data_2a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 N2 O2' _chemical_formula_weight 182.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7692(3) _cell_length_b 7.9733(4) _cell_length_c 10.1316(5) _cell_angle_alpha 79.224(3) _cell_angle_beta 89.598(3) _cell_angle_gamma 81.603(3) _cell_volume 452.82(4) _cell_formula_units_Z 2 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 5494 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 4095 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0771 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2066 _reflns_number_gt 1486 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+0.1048P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.024(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2066 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1103 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4177(3) 0.8694(2) 0.26793(15) 0.0128(4) Uani 1 1 d . . . O2 O 0.2203(2) 0.82168(14) 0.48401(11) 0.0169(3) Uani 1 1 d . . . C2 C 0.2602(3) 0.9222(2) 0.38094(16) 0.0138(4) Uani 1 1 d . . . N3 N 0.1688(2) 1.09002(16) 0.35130(13) 0.0139(3) Uani 1 1 d . . . H3 H 0.0821 1.1405 0.4086 0.017 Uiso 1 1 calc R . . C4 C 0.2210(3) 1.1851(2) 0.21844(16) 0.0144(4) Uani 1 1 d . . . N5 N 0.1650(2) 1.08397(16) 0.11862(13) 0.0150(4) Uani 1 1 d . . . H5 H 0.0774 1.1310 0.0467 0.018 Uiso 1 1 calc R . . O6 O 0.2114(2) 0.80999(14) 0.07545(11) 0.0187(3) Uani 1 1 d . . . C6 C 0.2551(3) 0.9159(2) 0.14333(16) 0.0141(4) Uani 1 1 d . . . C7 C 0.6054(3) 0.9941(2) 0.24493(17) 0.0169(4) Uani 1 1 d . . . H7A H 0.7082 0.9740 0.3259 0.020 Uiso 1 1 calc R . . H7B H 0.7042 0.9700 0.1684 0.020 Uiso 1 1 calc R . . C8 C 0.4873(3) 1.1836(2) 0.21554(16) 0.0159(4) Uani 1 1 d . . . H8A H 0.5364 1.2456 0.2842 0.019 Uiso 1 1 calc R . . H8B H 0.5334 1.2419 0.1263 0.019 Uiso 1 1 calc R . . C9 C 0.5221(3) 0.6789(2) 0.29589(16) 0.0159(4) Uani 1 1 d . . . H9A H 0.5894 0.6484 0.2119 0.019 Uiso 1 1 calc R . . H9B H 0.3943 0.6095 0.3214 0.019 Uiso 1 1 calc R . . C10 C 0.7120(3) 0.6287(2) 0.40619(17) 0.0203(4) Uani 1 1 d . . . H10A H 0.8538(14) 0.6801(5) 0.3745(3) 0.030 Uiso 1 1 calc R . . H10B H 0.7519(5) 0.5012(13) 0.4281(3) 0.030 Uiso 1 1 calc R . . H10C H 0.6536(6) 0.6723(5) 0.4877(8) 0.030 Uiso 1 1 calc R . . C11 C 0.0803(3) 1.3635(2) 0.19061(17) 0.0186(4) Uani 1 1 d . . . H11A H 0.1241(5) 1.4265(7) 0.1032(9) 0.028 Uiso 1 1 calc R . . H11B H 0.1129(4) 1.4261(7) 0.2618(7) 0.028 Uiso 1 1 calc R . . H11C H -0.0878(17) 1.3542(2) 0.18867(17) 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0128(9) 0.0146(9) 0.0123(9) -0.0045(7) -0.0004(7) -0.0031(7) O2 0.0177(7) 0.0179(6) 0.0144(6) -0.0009(5) 0.0020(5) -0.0029(5) C2 0.0114(9) 0.0182(9) 0.0135(9) -0.0046(7) -0.0020(7) -0.0057(7) N3 0.0169(8) 0.0144(8) 0.0120(7) -0.0058(6) 0.0034(6) -0.0033(6) C4 0.0157(9) 0.0167(9) 0.0117(9) -0.0033(7) -0.0009(7) -0.0040(7) N5 0.0186(8) 0.0160(8) 0.0111(7) -0.0033(6) -0.0032(6) -0.0038(6) O6 0.0209(7) 0.0196(7) 0.0174(7) -0.0079(5) -0.0028(5) -0.0035(5) C6 0.0117(9) 0.0186(9) 0.0130(9) -0.0039(7) 0.0031(7) -0.0047(7) C7 0.0142(9) 0.0219(10) 0.0161(9) -0.0055(7) 0.0011(7) -0.0049(7) C8 0.0169(10) 0.0181(9) 0.0137(9) -0.0033(7) 0.0015(7) -0.0059(7) C9 0.0166(10) 0.0180(9) 0.0144(9) -0.0061(7) 0.0009(7) -0.0024(7) C10 0.0197(10) 0.0192(10) 0.0212(10) -0.0039(8) -0.0020(8) -0.0008(8) C11 0.0197(10) 0.0175(10) 0.0196(9) -0.0042(8) -0.0003(8) -0.0049(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C9 1.524(2) . ? C1 C6 1.533(2) . ? C1 C2 1.539(2) . ? C1 C7 1.562(2) . ? O2 C2 1.2340(19) . ? C2 N3 1.343(2) . ? N3 C4 1.469(2) . ? N3 H3 0.8800 . ? C4 N5 1.471(2) . ? C4 C11 1.509(2) . ? C4 C8 1.535(2) . ? N5 C6 1.342(2) . ? N5 H5 0.8800 . ? O6 C6 1.2373(18) . ? C7 C8 1.540(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.526(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9924 . ? C10 H10B 0.9924 . ? C10 H10C 0.9924 . ? C11 H11A 0.9839 . ? C11 H11B 0.9839 . ? C11 H11C 0.9839 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C1 C6 111.95(13) . . ? C9 C1 C2 113.18(13) . . ? C6 C1 C2 103.81(13) . . ? C9 C1 C7 113.69(13) . . ? C6 C1 C7 106.74(13) . . ? C2 C1 C7 106.76(13) . . ? O2 C2 N3 124.76(15) . . ? O2 C2 C1 123.99(14) . . ? N3 C2 C1 111.23(14) . . ? C2 N3 C4 116.68(13) . . ? C2 N3 H3 121.7 . . ? C4 N3 H3 121.7 . . ? N3 C4 N5 107.29(12) . . ? N3 C4 C11 111.04(13) . . ? N5 C4 C11 110.89(13) . . ? N3 C4 C8 106.67(13) . . ? N5 C4 C8 106.51(13) . . ? C11 C4 C8 114.07(14) . . ? C6 N5 C4 116.25(13) . . ? C6 N5 H5 121.9 . . ? C4 N5 H5 121.9 . . ? O6 C6 N5 124.62(15) . . ? O6 C6 C1 123.68(14) . . ? N5 C6 C1 111.70(13) . . ? C8 C7 C1 110.73(13) . . ? C8 C7 H7A 109.5 . . ? C1 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C4 C8 C7 107.91(13) . . ? C4 C8 H8A 110.1 . . ? C7 C8 H8A 110.1 . . ? C4 C8 H8B 110.1 . . ? C7 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C1 C9 C10 114.75(13) . . ? C1 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? C1 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 O2 -0.2(2) . . . . ? C6 C1 C2 O2 121.37(16) . . . . ? C7 C1 C2 O2 -126.06(16) . . . . ? C9 C1 C2 N3 -178.97(13) . . . . ? C6 C1 C2 N3 -57.36(16) . . . . ? C7 C1 C2 N3 55.20(17) . . . . ? O2 C2 N3 C4 -174.86(15) . . . . ? C1 C2 N3 C4 3.86(19) . . . . ? C2 N3 C4 N5 50.44(18) . . . . ? C2 N3 C4 C11 171.77(13) . . . . ? C2 N3 C4 C8 -63.38(17) . . . . ? N3 C4 N5 C6 -49.82(18) . . . . ? C11 C4 N5 C6 -171.24(14) . . . . ? C8 C4 N5 C6 64.11(17) . . . . ? C4 N5 C6 O6 174.37(15) . . . . ? C4 N5 C6 C1 -4.88(19) . . . . ? C9 C1 C6 O6 1.2(2) . . . . ? C2 C1 C6 O6 -121.23(17) . . . . ? C7 C1 C6 O6 126.19(16) . . . . ? C9 C1 C6 N5 -179.54(13) . . . . ? C2 C1 C6 N5 58.04(16) . . . . ? C7 C1 C6 N5 -54.55(17) . . . . ? C9 C1 C7 C8 179.26(13) . . . . ? C6 C1 C7 C8 55.32(17) . . . . ? C2 C1 C7 C8 -55.21(16) . . . . ? N3 C4 C8 C7 57.24(15) . . . . ? N5 C4 C8 C7 -57.12(15) . . . . ? C11 C4 C8 C7 -179.79(13) . . . . ? C1 C7 C8 C4 -0.21(17) . . . . ? C6 C1 C9 C10 171.75(14) . . . . ? C2 C1 C9 C10 -71.35(18) . . . . ? C7 C1 C9 C10 50.69(19) . . . . ? _diffrn_measured_fraction_theta_max .996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full .996 _refine_diff_density_max .282 _refine_diff_density_min -.282 _refine_diff_density_rms .053 #===END data_2b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 N2 O2' _chemical_formula_weight 210.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0180(4) _cell_length_b 9.7880(7) _cell_length_c 9.9340(8) _cell_angle_alpha 108.985(4) _cell_angle_beta 90.136(4) _cell_angle_gamma 96.233(4) _cell_volume 549.61(7) _cell_formula_units_Z 2 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 4720 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9724 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 3865 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2515 _reflns_number_gt 1789 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.2533P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2515 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3884(3) 0.12880(17) 0.28920(17) 0.0137(4) Uani 1 1 d . . . O2 O 0.18443(19) 0.17148(12) 0.50955(12) 0.0194(3) Uani 1 1 d . . . C2 C 0.2348(3) 0.08531(18) 0.39536(17) 0.0149(4) Uani 1 1 d . . . N3 N 0.1627(2) -0.05787(14) 0.34750(14) 0.0164(3) Uani 1 1 d . . . H3 H 0.0782 -0.0996 0.3986 0.020 Uiso 1 1 calc R . . C4 C 0.2324(3) -0.14084(17) 0.20566(17) 0.0156(4) Uani 1 1 d . . . N5 N 0.1781(2) -0.06398(14) 0.10750(14) 0.0154(3) Uani 1 1 d . . . H5 H 0.1046 -0.1092 0.0256 0.018 Uiso 1 1 calc R . . O6 O 0.19803(18) 0.16198(12) 0.08616(12) 0.0171(3) Uani 1 1 d . . . C6 C 0.2471(3) 0.07952(17) 0.14986(17) 0.0136(4) Uani 1 1 d . . . C7 C 0.5826(3) 0.03049(17) 0.26712(18) 0.0170(4) Uani 1 1 d . . . H7A H 0.6844 0.0504 0.1959 0.020 Uiso 1 1 calc R . . H7B H 0.6698 0.0539 0.3580 0.020 Uiso 1 1 calc R . . C8 C 0.4887(3) -0.13199(18) 0.21562(18) 0.0171(4) Uani 1 1 d . . . H8A H 0.5463 -0.1822 0.1212 0.020 Uiso 1 1 calc R . . H8B H 0.5349 -0.1793 0.2837 0.020 Uiso 1 1 calc R . . C9 C 0.1110(3) -0.29322(18) 0.15808(19) 0.0205(4) Uani 1 1 d . . . H9A H 0.1421 -0.3411 0.2276 0.031 Uiso 1 1 calc R . . H9B H 0.1626 -0.3487 0.0648 0.031 Uiso 1 1 calc R . . H9C H -0.0503 -0.2886 0.1510 0.031 Uiso 1 1 calc R . . C10 C 0.4655(3) 0.29169(17) 0.34016(17) 0.0154(4) Uani 1 1 d . . . H10A H 0.5402 0.3185 0.4356 0.018 Uiso 1 1 calc R . . H10B H 0.3319 0.3445 0.3509 0.018 Uiso 1 1 calc R . . C11 C 0.6272(3) 0.34410(18) 0.24137(18) 0.0166(4) Uani 1 1 d . . . H11 H 0.6336 0.2614 0.1508 0.020 Uiso 1 1 calc R . . C12 C 0.8628(3) 0.38917(19) 0.3092(2) 0.0241(4) Uani 1 1 d . . . H12A H 0.9661 0.4077 0.2394 0.036 Uiso 1 1 calc R . . H12B H 0.9100 0.3110 0.3401 0.036 Uiso 1 1 calc R . . H12C H 0.8637 0.4778 0.3917 0.036 Uiso 1 1 calc R . . C13 C 0.5419(3) 0.47002(19) 0.2049(2) 0.0228(4) Uani 1 1 d . . . H13A H 0.5351 0.5525 0.2924 0.034 Uiso 1 1 calc R . . H13B H 0.3922 0.4388 0.1591 0.034 Uiso 1 1 calc R . . H13C H 0.6439 0.4994 0.1399 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0123(8) 0.0158(8) 0.0131(8) 0.0051(7) 0.0008(7) 0.0013(6) O2 0.0220(7) 0.0203(7) 0.0149(6) 0.0049(5) 0.0038(5) 0.0008(5) C2 0.0129(8) 0.0186(9) 0.0141(8) 0.0064(7) -0.0023(7) 0.0028(7) N3 0.0182(8) 0.0165(7) 0.0160(7) 0.0077(6) 0.0050(6) 0.0012(6) C4 0.0179(9) 0.0154(9) 0.0153(8) 0.0071(7) 0.0016(7) 0.0034(7) N5 0.0173(8) 0.0155(7) 0.0133(7) 0.0051(6) -0.0024(6) 0.0009(6) O6 0.0169(6) 0.0180(6) 0.0179(6) 0.0084(5) -0.0024(5) 0.0009(5) C6 0.0099(8) 0.0175(9) 0.0136(8) 0.0049(7) 0.0029(7) 0.0026(6) C7 0.0134(8) 0.0209(9) 0.0180(9) 0.0081(7) -0.0018(7) 0.0027(7) C8 0.0164(9) 0.0196(9) 0.0177(8) 0.0087(7) 0.0024(7) 0.0053(7) C9 0.0228(10) 0.0172(9) 0.0215(9) 0.0065(8) 0.0020(8) 0.0019(7) C10 0.0131(8) 0.0182(9) 0.0143(8) 0.0044(7) -0.0004(7) 0.0021(7) C11 0.0162(9) 0.0165(9) 0.0160(8) 0.0042(7) 0.0005(7) 0.0006(7) C12 0.0175(9) 0.0257(10) 0.0297(10) 0.0106(8) 0.0006(8) -0.0006(7) C13 0.0229(10) 0.0225(10) 0.0253(10) 0.0107(8) 0.0045(8) 0.0039(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C10 1.525(2) . ? C1 C6 1.531(2) . ? C1 C2 1.536(2) . ? C1 C7 1.565(2) . ? O2 C2 1.2347(19) . ? C2 N3 1.346(2) . ? N3 C4 1.467(2) . ? N3 H3 0.8800 . ? C4 N5 1.467(2) . ? C4 C9 1.512(2) . ? C4 C8 1.536(2) . ? N5 C6 1.345(2) . ? N5 H5 0.8800 . ? O6 C6 1.2337(19) . ? C7 C8 1.544(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.548(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.525(2) . ? C11 C13 1.530(2) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C1 C6 112.48(13) . . ? C10 C1 C2 111.78(13) . . ? C6 C1 C2 104.36(12) . . ? C10 C1 C7 114.40(13) . . ? C6 C1 C7 107.45(13) . . ? C2 C1 C7 105.66(13) . . ? O2 C2 N3 124.79(15) . . ? O2 C2 C1 123.94(14) . . ? N3 C2 C1 111.28(14) . . ? C2 N3 C4 116.56(13) . . ? C2 N3 H3 121.7 . . ? C4 N3 H3 121.7 . . ? N5 C4 N3 107.57(13) . . ? N5 C4 C9 110.45(13) . . ? N3 C4 C9 110.14(13) . . ? N5 C4 C8 106.80(13) . . ? N3 C4 C8 106.49(13) . . ? C9 C4 C8 115.04(14) . . ? C6 N5 C4 116.16(13) . . ? C6 N5 H5 121.9 . . ? C4 N5 H5 121.9 . . ? O6 C6 N5 124.21(15) . . ? O6 C6 C1 124.09(14) . . ? N5 C6 C1 111.68(14) . . ? C8 C7 C1 110.65(13) . . ? C8 C7 H7A 109.5 . . ? C1 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C4 C8 C7 107.69(13) . . ? C4 C8 H8A 110.2 . . ? C7 C8 H8A 110.2 . . ? C4 C8 H8B 110.2 . . ? C7 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 C11 115.13(14) . . ? C1 C10 H10A 108.5 . . ? C11 C10 H10A 108.5 . . ? C1 C10 H10B 108.5 . . ? C11 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C13 110.29(14) . . ? C12 C11 C10 111.10(14) . . ? C13 C11 C10 110.78(14) . . ? C12 C11 H11 108.2 . . ? C13 C11 H11 108.2 . . ? C10 C11 H11 108.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 O2 -1.6(2) . . . . ? C6 C1 C2 O2 -123.42(16) . . . . ? C7 C1 C2 O2 123.42(16) . . . . ? C10 C1 C2 N3 178.27(13) . . . . ? C6 C1 C2 N3 56.45(17) . . . . ? C7 C1 C2 N3 -56.70(17) . . . . ? O2 C2 N3 C4 177.05(15) . . . . ? C1 C2 N3 C4 -2.83(19) . . . . ? C2 N3 C4 N5 -51.02(18) . . . . ? C2 N3 C4 C9 -171.45(14) . . . . ? C2 N3 C4 C8 63.18(17) . . . . ? N3 C4 N5 C6 49.65(18) . . . . ? C9 C4 N5 C6 169.89(13) . . . . ? C8 C4 N5 C6 -64.35(17) . . . . ? C4 N5 C6 O6 -173.29(14) . . . . ? C4 N5 C6 C1 5.08(19) . . . . ? C10 C1 C6 O6 -0.8(2) . . . . ? C2 C1 C6 O6 120.54(16) . . . . ? C7 C1 C6 O6 -127.60(16) . . . . ? C10 C1 C6 N5 -179.19(13) . . . . ? C2 C1 C6 N5 -57.83(16) . . . . ? C7 C1 C6 N5 54.04(16) . . . . ? C10 C1 C7 C8 -179.98(13) . . . . ? C6 C1 C7 C8 -54.34(17) . . . . ? C2 C1 C7 C8 56.64(17) . . . . ? N5 C4 C8 C7 57.74(16) . . . . ? N3 C4 C8 C7 -56.98(16) . . . . ? C9 C4 C8 C7 -179.31(14) . . . . ? C1 C7 C8 C4 -0.74(18) . . . . ? C6 C1 C10 C11 -64.78(18) . . . . ? C2 C1 C10 C11 178.20(13) . . . . ? C7 C1 C10 C11 58.18(19) . . . . ? C1 C10 C11 C12 -109.46(16) . . . . ? C1 C10 C11 C13 127.59(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.367 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.053 #===END data_2c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 N2 O2' _chemical_formula_weight 216.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.92500(10) _cell_length_b 7.7000(2) _cell_length_c 10.4730(2) _cell_angle_alpha 104.6480(9) _cell_angle_beta 103.7130(9) _cell_angle_gamma 91.7510(9) _cell_volume 522.456(18) _cell_formula_units_Z 2 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 2360 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 4715 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.43 _reflns_number_total 2370 _reflns_number_gt 1637 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2370 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4466(2) 0.45109(19) 0.15119(14) 0.0174(4) Uani 1 1 d . . . H1 H 0.5307 0.5413 0.1287 0.021 Uiso 1 1 calc R . . O2 O 0.59609(15) 0.60380(14) 0.38918(10) 0.0217(3) Uani 1 1 d . . . C2 C 0.4830(2) 0.4794(2) 0.30353(15) 0.0177(3) Uani 1 1 d . . . N3 N 0.37289(18) 0.35369(16) 0.33113(12) 0.0181(3) Uani 1 1 d . . . H3 H 0.3763 0.3524 0.4154 0.022 Uiso 1 1 calc R . . C4 C 0.2461(2) 0.21799(19) 0.21291(14) 0.0168(3) Uani 1 1 d . . . N5 N 0.37774(17) 0.14164(16) 0.12502(12) 0.0172(3) Uani 1 1 d . . . H5 H 0.3861 0.0248 0.0985 0.021 Uiso 1 1 calc R . . O6 O 0.59415(15) 0.22060(13) 0.00945(10) 0.0205(3) Uani 1 1 d . . . C6 C 0.4840(2) 0.26010(19) 0.08779(14) 0.0171(4) Uani 1 1 d . . . C7 C 0.2199(2) 0.4633(2) 0.09494(16) 0.0199(4) Uani 1 1 d . . . H7A H 0.1848 0.5855 0.1344 0.024 Uiso 1 1 calc R . . H7B H 0.1878 0.4411 -0.0055 0.024 Uiso 1 1 calc R . . C8 C 0.0986(2) 0.3216(2) 0.13289(15) 0.0201(4) Uani 1 1 d . . . H8A H 0.0111 0.3817 0.1895 0.024 Uiso 1 1 calc R . . H8B H 0.0135 0.2373 0.0493 0.024 Uiso 1 1 calc R . . C9 C 0.1547(2) 0.07159(19) 0.25994(14) 0.0173(3) Uani 1 1 d . . . C10 C -0.0505(2) 0.0283(2) 0.22729(15) 0.0206(4) Uani 1 1 d . . . H10 H -0.1373 0.0894 0.1724 0.025 Uiso 1 1 calc R . . C11 C -0.1292(2) -0.1045(2) 0.27489(16) 0.0237(4) Uani 1 1 d . . . H11 H -0.2696 -0.1341 0.2516 0.028 Uiso 1 1 calc R . . C12 C -0.0050(2) -0.1931(2) 0.35548(16) 0.0233(4) Uani 1 1 d . . . H12 H -0.0595 -0.2823 0.3886 0.028 Uiso 1 1 calc R . . C13 C 0.1994(2) -0.1511(2) 0.38772(15) 0.0218(4) Uani 1 1 d . . . H13 H 0.2856 -0.2120 0.4430 0.026 Uiso 1 1 calc R . . C14 C 0.2791(2) -0.0207(2) 0.33981(15) 0.0203(4) Uani 1 1 d . . . H14 H 0.4198 0.0062 0.3616 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0171(8) 0.0178(8) 0.0176(8) 0.0054(6) 0.0046(6) -0.0017(6) O2 0.0220(6) 0.0218(6) 0.0185(6) 0.0027(5) 0.0041(5) -0.0057(5) C2 0.0152(8) 0.0181(8) 0.0199(8) 0.0049(6) 0.0047(6) 0.0014(6) N3 0.0207(7) 0.0197(7) 0.0135(6) 0.0042(5) 0.0043(5) -0.0027(5) C4 0.0151(8) 0.0184(8) 0.0156(7) 0.0023(6) 0.0043(6) -0.0006(6) N5 0.0191(7) 0.0147(6) 0.0191(7) 0.0041(5) 0.0075(6) 0.0009(5) O6 0.0214(6) 0.0220(6) 0.0206(6) 0.0058(5) 0.0099(5) 0.0019(5) C6 0.0152(8) 0.0206(8) 0.0141(7) 0.0061(6) -0.0003(6) 0.0012(6) C7 0.0194(8) 0.0206(8) 0.0200(8) 0.0065(6) 0.0041(6) 0.0034(6) C8 0.0181(8) 0.0217(8) 0.0199(8) 0.0051(7) 0.0042(7) 0.0002(6) C9 0.0200(9) 0.0167(8) 0.0139(7) 0.0005(6) 0.0062(6) -0.0013(6) C10 0.0197(9) 0.0228(8) 0.0178(8) 0.0036(7) 0.0039(7) 0.0002(7) C11 0.0191(9) 0.0243(9) 0.0251(9) 0.0012(7) 0.0074(7) -0.0043(7) C12 0.0281(9) 0.0187(8) 0.0259(9) 0.0049(7) 0.0137(7) -0.0021(7) C13 0.0256(9) 0.0204(8) 0.0209(8) 0.0060(7) 0.0078(7) 0.0025(7) C14 0.0176(8) 0.0206(8) 0.0219(8) 0.0039(7) 0.0061(7) -0.0007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.5104(19) . ? C1 C2 1.512(2) . ? C1 C7 1.556(2) . ? C1 H1 1.0000 . ? O2 C2 1.2336(18) . ? C2 N3 1.3428(19) . ? N3 C4 1.4731(18) . ? N3 H3 0.8800 . ? C4 N5 1.4767(18) . ? C4 C9 1.516(2) . ? C4 C8 1.538(2) . ? N5 C6 1.3417(18) . ? N5 H5 0.8800 . ? O6 C6 1.2378(16) . ? C7 C8 1.542(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.389(2) . ? C9 C14 1.394(2) . ? C10 C11 1.394(2) . ? C10 H10 0.9500 . ? C11 C12 1.379(2) . ? C11 H11 0.9500 . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.384(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 108.74(11) . . ? C6 C1 C7 105.78(12) . . ? C2 C1 C7 106.83(11) . . ? C6 C1 H1 111.7 . . ? C2 C1 H1 111.7 . . ? C7 C1 H1 111.7 . . ? O2 C2 N3 125.48(14) . . ? O2 C2 C1 123.85(13) . . ? N3 C2 C1 110.66(12) . . ? C2 N3 C4 116.49(12) . . ? C2 N3 H3 121.8 . . ? C4 N3 H3 121.8 . . ? N3 C4 N5 106.44(11) . . ? N3 C4 C9 110.09(11) . . ? N5 C4 C9 110.43(11) . . ? N3 C4 C8 106.51(12) . . ? N5 C4 C8 106.65(11) . . ? C9 C4 C8 116.20(12) . . ? C6 N5 C4 116.38(12) . . ? C6 N5 H5 121.8 . . ? C4 N5 H5 121.8 . . ? O6 C6 N5 125.41(14) . . ? O6 C6 C1 123.81(13) . . ? N5 C6 C1 110.76(12) . . ? C8 C7 C1 109.27(11) . . ? C8 C7 H7A 109.8 . . ? C1 C7 H7A 109.8 . . ? C8 C7 H7B 109.8 . . ? C1 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C4 C8 C7 108.20(12) . . ? C4 C8 H8A 110.1 . . ? C7 C8 H8A 110.1 . . ? C4 C8 H8B 110.1 . . ? C7 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C10 C9 C14 118.87(14) . . ? C10 C9 C4 121.79(13) . . ? C14 C9 C4 119.33(13) . . ? C9 C10 C11 120.14(14) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 120.52(15) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 119.56(15) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 120.32(15) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C9 120.58(14) . . ? C13 C14 H14 119.7 . . ? C9 C14 H14 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O2 126.78(15) . . . . ? C7 C1 C2 O2 -119.47(15) . . . . ? C6 C1 C2 N3 -54.44(16) . . . . ? C7 C1 C2 N3 59.31(15) . . . . ? O2 C2 N3 C4 179.42(13) . . . . ? C1 C2 N3 C4 0.66(17) . . . . ? C2 N3 C4 N5 52.33(16) . . . . ? C2 N3 C4 C9 172.03(12) . . . . ? C2 N3 C4 C8 -61.18(16) . . . . ? N3 C4 N5 C6 -53.95(15) . . . . ? C9 C4 N5 C6 -173.42(11) . . . . ? C8 C4 N5 C6 59.48(15) . . . . ? C4 N5 C6 O6 -176.29(13) . . . . ? C4 N5 C6 C1 1.91(16) . . . . ? C2 C1 C6 O6 -128.81(14) . . . . ? C7 C1 C6 O6 116.76(15) . . . . ? C2 C1 C6 N5 52.95(15) . . . . ? C7 C1 C6 N5 -61.48(14) . . . . ? C6 C1 C7 C8 58.31(15) . . . . ? C2 C1 C7 C8 -57.44(15) . . . . ? N3 C4 C8 C7 56.86(15) . . . . ? N5 C4 C8 C7 -56.52(15) . . . . ? C9 C4 C8 C7 179.90(12) . . . . ? C1 C7 C8 C4 -0.15(16) . . . . ? N3 C4 C9 C10 123.91(14) . . . . ? N5 C4 C9 C10 -118.84(14) . . . . ? C8 C4 C9 C10 2.8(2) . . . . ? N3 C4 C9 C14 -55.13(17) . . . . ? N5 C4 C9 C14 62.12(16) . . . . ? C8 C4 C9 C14 -176.28(12) . . . . ? C14 C9 C10 C11 0.4(2) . . . . ? C4 C9 C10 C11 -178.61(14) . . . . ? C9 C10 C11 C12 0.5(2) . . . . ? C10 C11 C12 C13 -0.8(2) . . . . ? C11 C12 C13 C14 0.2(2) . . . . ? C12 C13 C14 C9 0.8(2) . . . . ? C10 C9 C14 C13 -1.1(2) . . . . ? C4 C9 C14 C13 177.99(14) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.286 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.051 #===END data_2e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 N2 O2' _chemical_formula_weight 196.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.6414(4) _cell_length_b 10.0737(7) _cell_length_c 8.6069(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.624(4) _cell_angle_gamma 90.00 _cell_volume 485.86(6) _cell_formula_units_Z 2 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 4692 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 3756 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0591 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1176 _reflns_number_gt 898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.2317P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1176 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 2.160 _refine_ls_shift/su_mean 0.030 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.31923(18) 0.04855(11) 0.81947(12) 0.0157(3) Uani 1 1 d . . . C1 C 0.0848(4) 0.2500 0.8555(3) 0.0119(5) Uani 1 2 d S . . C2 C 0.2472(3) 0.13123(16) 0.90894(18) 0.0123(4) Uani 1 1 d . . . N3 N 0.3075(2) 0.13264(13) 1.06464(14) 0.0133(3) Uani 1 1 d . . . H3 H 0.3858 0.0664 1.1135 0.016 Uiso 1 1 calc R . . C4 C 0.2366(4) 0.2500 1.1493(3) 0.0132(5) Uani 1 2 d S . . C5 C -0.1268(4) 0.2500 0.9581(3) 0.0144(5) Uani 1 2 d S . . H5A H -0.2271 0.3295 0.9330 0.017 Uiso 0.50 1 calc PR . . H5B H -0.2271 0.1705 0.9330 0.017 Uiso 0.50 1 calc PR . . C6 C -0.0366(4) 0.2500 1.1340(3) 0.0141(5) Uani 1 2 d S . . H6A H -0.0952 0.3298 1.1849 0.017 Uiso 0.50 1 calc PR . . H6B H -0.0952 0.1702 1.1849 0.017 Uiso 0.50 1 calc PR . . C7 C 0.3568(4) 0.2500 1.3154(2) 0.0164(5) Uani 1 2 d S . . H7A H 0.3048 0.3279 1.3707 0.025 Uiso 0.50 1 calc PR . . H7B H 0.5303 0.2530 1.3146 0.025 Uiso 1 2 calc SR . . H7C H 0.3132 0.1691 1.3686 0.025 Uiso 0.50 1 calc PR . . C8 C 0.0028(4) 0.2500 0.6789(3) 0.0147(5) Uani 1 2 d S . . H8 H 0.1492 0.2500 0.6236 0.018 Uiso 1 2 calc SR . . C9 C -0.1429(3) 0.12614(17) 0.62552(19) 0.0186(4) Uani 1 1 d . . . H9A H -0.2980 0.1296 0.6662 0.028 Uiso 1 1 calc R . . H9B H -0.0565 0.0465 0.6653 0.028 Uiso 1 1 calc R . . H9C H -0.1673 0.1233 0.5110 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0139(6) 0.0149(6) 0.0181(6) -0.0033(5) 0.0015(5) 0.0023(5) C1 0.0097(11) 0.0115(11) 0.0147(12) 0.000 0.0025(9) 0.000 C2 0.0082(7) 0.0118(8) 0.0171(8) -0.0001(7) 0.0021(6) -0.0032(6) N3 0.0127(7) 0.0116(7) 0.0155(7) 0.0016(5) 0.0014(5) 0.0035(5) C4 0.0117(11) 0.0125(12) 0.0154(12) 0.000 0.0017(9) 0.000 C5 0.0102(11) 0.0153(12) 0.0180(12) 0.000 0.0026(9) 0.000 C6 0.0118(11) 0.0130(12) 0.0180(12) 0.000 0.0038(9) 0.000 C7 0.0169(12) 0.0180(13) 0.0144(12) 0.000 0.0021(10) 0.000 C8 0.0136(11) 0.0149(12) 0.0154(12) 0.000 0.0012(9) 0.000 C9 0.0194(9) 0.0172(9) 0.0182(9) -0.0011(7) -0.0018(7) 0.0005(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.2346(18) . ? C1 C8 1.537(3) . ? C1 C2 1.544(2) . ? C1 C2 1.544(2) 4_565 ? C1 C5 1.565(3) . ? C2 N3 1.3442(19) . ? N3 C4 1.4681(18) . ? N3 H3 0.8800 . ? C4 N3 1.4681(18) 4_565 ? C4 C7 1.510(3) . ? C4 C6 1.532(3) . ? C5 C6 1.540(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9803 . ? C7 H7B 0.9803 . ? C7 H7C 0.9803 . ? C8 C9 1.535(2) 4_565 ? C8 C9 1.535(2) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C1 C2 113.27(12) . . ? C8 C1 C2 113.27(12) . 4_565 ? C2 C1 C2 101.58(16) . 4_565 ? C8 C1 C5 113.31(17) . . ? C2 C1 C5 107.27(12) . . ? C2 C1 C5 107.27(12) 4_565 . ? O1 C2 N3 124.42(14) . . ? O1 C2 C1 124.31(15) . . ? N3 C2 C1 111.22(14) . . ? C2 N3 C4 116.81(14) . . ? C2 N3 H3 121.6 . . ? C4 N3 H3 121.6 . . ? N3 C4 N3 107.27(17) 4_565 . ? N3 C4 C7 110.58(12) 4_565 . ? N3 C4 C7 110.58(12) . . ? N3 C4 C6 106.64(12) 4_565 . ? N3 C4 C6 106.64(12) . . ? C7 C4 C6 114.76(19) . . ? C6 C5 C1 111.56(17) . . ? C6 C5 H5A 109.3 . . ? C1 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C1 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C4 C6 C5 107.44(18) . . ? C4 C6 H6A 110.2 . . ? C5 C6 H6A 110.2 . . ? C4 C6 H6B 110.2 . . ? C5 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.4 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.4 . . ? H7B C7 H7C 109.4 . . ? C9 C8 C9 108.74(18) 4_565 . ? C9 C8 C1 112.71(12) 4_565 . ? C9 C8 C1 112.70(12) . . ? C9 C8 H8 107.5 4_565 . ? C9 C8 H8 107.5 . . ? C1 C8 H8 107.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C1 C2 O1 4.7(2) . . . . ? C2 C1 C2 O1 -117.10(15) 4_565 . . . ? C5 C1 C2 O1 130.50(16) . . . . ? C8 C1 C2 N3 -177.79(13) . . . . ? C2 C1 C2 N3 60.40(19) 4_565 . . . ? C5 C1 C2 N3 -51.99(16) . . . . ? O1 C2 N3 C4 170.40(15) . . . . ? C1 C2 N3 C4 -7.11(19) . . . . ? C2 N3 C4 N3 -48.2(2) . . . 4_565 ? C2 N3 C4 C7 -168.88(14) . . . . ? C2 N3 C4 C6 65.73(18) . . . . ? C8 C1 C5 C6 180.0 . . . . ? C2 C1 C5 C6 54.23(11) . . . . ? C2 C1 C5 C6 -54.23(10) 4_565 . . . ? N3 C4 C6 C5 57.19(11) 4_565 . . . ? N3 C4 C6 C5 -57.19(11) . . . . ? C7 C4 C6 C5 180.000(1) . . . . ? C1 C5 C6 C4 0.000(1) . . . . ? C2 C1 C8 C9 -175.74(14) . . . 4_565 ? C2 C1 C8 C9 -60.7(2) 4_565 . . 4_565 ? C5 C1 C8 C9 61.77(14) . . . 4_565 ? C2 C1 C8 C9 60.7(2) . . . . ? C2 C1 C8 C9 175.73(14) 4_565 . . . ? C5 C1 C8 C9 -61.77(14) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max .288 _refine_diff_density_min -.306 _refine_diff_density_rms .053 #===END data_2f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 N2 O2' _chemical_formula_weight 306.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.62800(10) _cell_length_b 10.2360(2) _cell_length_c 13.2680(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.1120(9) _cell_angle_gamma 90.00 _cell_volume 764.20(3) _cell_formula_units_Z 2 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9930 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 3422 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3422 _reflns_number_gt 3079 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.2003P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(12) _refine_ls_number_reflns 3422 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2910(3) -0.16101(19) 0.13755(11) 0.0163(3) Uani 1 1 d . . . O2 O 0.0686(2) 0.04256(12) 0.11973(9) 0.0207(3) Uani 1 1 d . . . C2 C 0.1747(3) -0.04785(17) 0.07868(13) 0.0174(3) Uani 1 1 d . . . N3 N 0.2054(3) -0.05915(14) -0.02100(11) 0.0180(3) Uani 1 1 d . . . H3 H 0.1501 -0.0005 -0.0639 0.022 Uiso 1 1 calc R . . C4 C 0.3369(3) -0.17514(17) -0.05445(12) 0.0165(3) Uani 1 1 d . . . N5 N 0.2263(3) -0.29011(15) -0.00904(11) 0.0184(3) Uani 1 1 d . . . H5 H 0.1901 -0.3598 -0.0450 0.022 Uiso 1 1 calc R . . O6 O 0.0638(2) -0.36530(12) 0.13589(9) 0.0222(3) Uani 1 1 d . . . C6 C 0.1827(3) -0.28407(17) 0.08991(13) 0.0165(3) Uani 1 1 d . . . C7 C 0.5596(3) -0.1573(2) 0.10902(12) 0.0197(3) Uani 1 1 d . . . H7A H 0.6328 -0.0759 0.1352 0.024 Uiso 1 1 calc R . . H7B H 0.6435 -0.2321 0.1409 0.024 Uiso 1 1 calc R . . C8 C 0.5878(3) -0.1637(2) -0.00644(12) 0.0203(3) Uani 1 1 d . . . H8A H 0.6676 -0.0838 -0.0308 0.024 Uiso 1 1 calc R . . H8B H 0.6852 -0.2403 -0.0248 0.024 Uiso 1 1 calc R . . C9 C 0.3223(3) -0.19253(16) -0.16825(12) 0.0176(4) Uani 1 1 d . . . C10 C 0.1184(3) -0.15402(19) -0.22243(12) 0.0213(4) Uani 1 1 d . . . H10 H -0.0042 -0.1077 -0.1896 0.026 Uiso 1 1 calc R . . C11 C 0.0954(3) -0.18367(19) -0.32449(13) 0.0233(4) Uani 1 1 d . . . H11 H -0.0421 -0.1560 -0.3612 0.028 Uiso 1 1 calc R . . C12 C 0.2702(3) -0.25297(18) -0.37305(14) 0.0233(4) Uani 1 1 d . . . H12 H 0.2516 -0.2748 -0.4423 0.028 Uiso 1 1 calc R . . C13 C 0.4727(3) -0.29019(19) -0.31955(14) 0.0236(4) Uani 1 1 d . . . H13 H 0.5953 -0.3359 -0.3529 0.028 Uiso 1 1 calc R . . C14 C 0.4984(3) -0.26132(18) -0.21755(14) 0.0222(4) Uani 1 1 d . . . H14 H 0.6370 -0.2887 -0.1814 0.027 Uiso 1 1 calc R . . C15 C 0.2441(3) -0.14770(18) 0.25063(12) 0.0187(3) Uani 1 1 d . . . H15A H 0.2605 -0.0546 0.2696 0.022 Uiso 1 1 calc R . . H15B H 0.0777 -0.1737 0.2628 0.022 Uiso 1 1 calc R . . C16 C 0.4062(3) -0.22783(18) 0.31885(13) 0.0202(4) Uani 1 1 d . . . C17 C 0.3570(3) -0.35824(19) 0.34096(13) 0.0240(4) Uani 1 1 d . . . H17 H 0.2175 -0.3980 0.3136 0.029 Uiso 1 1 calc R . . C18 C 0.5105(4) -0.4308(2) 0.40277(15) 0.0303(5) Uani 1 1 d . . . H18 H 0.4747 -0.5193 0.4178 0.036 Uiso 1 1 calc R . . C19 C 0.7149(4) -0.3739(2) 0.44232(15) 0.0315(5) Uani 1 1 d . . . H19 H 0.8210 -0.4239 0.4833 0.038 Uiso 1 1 calc R . . C20 C 0.7649(3) -0.2442(2) 0.42220(14) 0.0289(4) Uani 1 1 d . . . H20 H 0.9042 -0.2049 0.4501 0.035 Uiso 1 1 calc R . . C21 C 0.6111(3) -0.1715(2) 0.36120(13) 0.0249(4) Uani 1 1 d . . . H21 H 0.6458 -0.0823 0.3481 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0165(7) 0.0178(8) 0.0146(7) -0.0005(7) -0.0023(5) 0.0002(7) O2 0.0241(6) 0.0189(6) 0.0190(6) -0.0022(5) -0.0016(5) 0.0035(5) C2 0.0150(8) 0.0174(8) 0.0196(8) -0.0002(7) -0.0018(6) -0.0026(6) N3 0.0208(7) 0.0171(7) 0.0162(7) 0.0020(6) -0.0007(5) 0.0019(6) C4 0.0154(7) 0.0173(8) 0.0167(8) -0.0007(7) 0.0003(6) -0.0001(7) N5 0.0206(7) 0.0154(7) 0.0192(7) -0.0033(6) -0.0002(5) -0.0018(6) O6 0.0253(7) 0.0215(7) 0.0198(6) 0.0009(5) -0.0002(5) -0.0042(5) C6 0.0158(8) 0.0164(8) 0.0173(8) 0.0015(7) -0.0013(6) 0.0013(6) C7 0.0150(7) 0.0251(9) 0.0190(8) 0.0004(8) -0.0026(6) -0.0002(7) C8 0.0157(7) 0.0257(9) 0.0193(8) -0.0018(8) -0.0009(6) 0.0003(8) C9 0.0188(7) 0.0182(9) 0.0159(8) 0.0015(6) 0.0014(6) -0.0016(6) C10 0.0191(7) 0.0242(9) 0.0206(8) -0.0013(8) -0.0006(6) 0.0014(8) C11 0.0217(8) 0.0281(10) 0.0201(8) 0.0013(8) -0.0036(6) 0.0011(7) C12 0.0288(9) 0.0255(9) 0.0156(8) -0.0014(7) 0.0004(7) -0.0016(7) C13 0.0272(9) 0.0222(9) 0.0216(9) -0.0003(7) 0.0045(7) 0.0035(7) C14 0.0223(8) 0.0230(9) 0.0211(9) 0.0008(7) -0.0013(7) 0.0021(7) C15 0.0194(7) 0.0202(8) 0.0164(8) -0.0013(7) -0.0022(6) 0.0016(7) C16 0.0213(8) 0.0254(9) 0.0140(8) -0.0028(7) 0.0015(6) 0.0045(7) C17 0.0289(9) 0.0249(9) 0.0183(9) -0.0022(8) 0.0012(7) 0.0026(8) C18 0.0408(11) 0.0279(11) 0.0224(10) 0.0020(8) 0.0036(8) 0.0106(9) C19 0.0324(10) 0.0422(12) 0.0199(9) 0.0027(9) -0.0009(8) 0.0183(9) C20 0.0228(9) 0.0466(12) 0.0174(8) -0.0017(9) 0.0003(7) 0.0050(8) C21 0.0236(8) 0.0323(10) 0.0188(8) 0.0007(9) 0.0000(6) -0.0009(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.530(2) . ? C1 C15 1.534(2) . ? C1 C2 1.536(2) . ? C1 C7 1.566(2) . ? O2 C2 1.234(2) . ? C2 N3 1.342(2) . ? N3 C4 1.472(2) . ? N3 H3 0.8800 . ? C4 N5 1.466(2) . ? C4 C9 1.521(2) . ? C4 C8 1.542(2) . ? N5 C6 1.342(2) . ? N5 H5 0.8800 . ? O6 C6 1.236(2) . ? C7 C8 1.545(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.390(2) . ? C9 C10 1.399(2) . ? C10 C11 1.391(2) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.514(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.396(3) . ? C16 C21 1.398(2) . ? C17 C18 1.394(3) . ? C17 H17 0.9500 . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.384(3) . ? C19 H19 0.9500 . ? C20 C21 1.389(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C15 113.71(14) . . ? C6 C1 C2 104.37(12) . . ? C15 C1 C2 110.51(14) . . ? C6 C1 C7 107.37(14) . . ? C15 C1 C7 114.79(12) . . ? C2 C1 C7 105.24(14) . . ? O2 C2 N3 124.92(16) . . ? O2 C2 C1 123.11(15) . . ? N3 C2 C1 111.97(14) . . ? C2 N3 C4 116.22(14) . . ? C2 N3 H3 121.9 . . ? C4 N3 H3 121.9 . . ? N5 C4 N3 107.66(12) . . ? N5 C4 C9 107.38(13) . . ? N3 C4 C9 112.08(13) . . ? N5 C4 C8 106.50(13) . . ? N3 C4 C8 106.01(13) . . ? C9 C4 C8 116.77(13) . . ? C6 N5 C4 116.88(14) . . ? C6 N5 H5 121.6 . . ? C4 N5 H5 121.6 . . ? O6 C6 N5 124.27(16) . . ? O6 C6 C1 124.40(15) . . ? N5 C6 C1 111.30(14) . . ? C8 C7 C1 110.91(12) . . ? C8 C7 H7A 109.5 . . ? C1 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 108.0 . . ? C4 C8 C7 107.59(12) . . ? C4 C8 H8A 110.2 . . ? C7 C8 H8A 110.2 . . ? C4 C8 H8B 110.2 . . ? C7 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? C14 C9 C10 119.11(16) . . ? C14 C9 C4 120.08(15) . . ? C10 C9 C4 120.33(14) . . ? C11 C10 C9 119.90(16) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 120.79(16) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 119.25(17) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C12 C13 C14 120.65(17) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C9 C14 C13 120.29(17) . . ? C9 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C1 115.05(14) . . ? C16 C15 H15A 108.5 . . ? C1 C15 H15A 108.5 . . ? C16 C15 H15B 108.5 . . ? C1 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C17 C16 C21 118.39(17) . . ? C17 C16 C15 121.62(16) . . ? C21 C16 C15 119.99(16) . . ? C18 C17 C16 120.67(18) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C19 C18 C17 120.0(2) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.07(18) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C21 119.96(19) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C16 120.86(19) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O2 125.55(17) . . . . ? C15 C1 C2 O2 2.9(2) . . . . ? C7 C1 C2 O2 -121.54(17) . . . . ? C6 C1 C2 N3 -55.20(16) . . . . ? C15 C1 C2 N3 -177.82(13) . . . . ? C7 C1 C2 N3 57.71(17) . . . . ? O2 C2 N3 C4 -179.79(15) . . . . ? C1 C2 N3 C4 1.0(2) . . . . ? C2 N3 C4 N5 51.37(17) . . . . ? C2 N3 C4 C9 169.24(14) . . . . ? C2 N3 C4 C8 -62.29(18) . . . . ? N3 C4 N5 C6 -47.71(17) . . . . ? C9 C4 N5 C6 -168.57(13) . . . . ? C8 C4 N5 C6 65.63(17) . . . . ? C4 N5 C6 O6 170.29(15) . . . . ? C4 N5 C6 C1 -7.51(19) . . . . ? C15 C1 C6 O6 1.4(2) . . . . ? C2 C1 C6 O6 -119.08(17) . . . . ? C7 C1 C6 O6 129.55(17) . . . . ? C15 C1 C6 N5 179.22(13) . . . . ? C2 C1 C6 N5 58.72(16) . . . . ? C7 C1 C6 N5 -52.65(17) . . . . ? C6 C1 C7 C8 55.64(19) . . . . ? C15 C1 C7 C8 -176.87(16) . . . . ? C2 C1 C7 C8 -55.14(19) . . . . ? N5 C4 C8 C7 -55.94(18) . . . . ? N3 C4 C8 C7 58.53(18) . . . . ? C9 C4 C8 C7 -175.83(15) . . . . ? C1 C7 C8 C4 -1.4(2) . . . . ? N5 C4 C9 C14 -86.50(18) . . . . ? N3 C4 C9 C14 155.47(15) . . . . ? C8 C4 C9 C14 32.9(2) . . . . ? N5 C4 C9 C10 85.52(18) . . . . ? N3 C4 C9 C10 -32.5(2) . . . . ? C8 C4 C9 C10 -155.07(16) . . . . ? C14 C9 C10 C11 -0.6(3) . . . . ? C4 C9 C10 C11 -172.71(16) . . . . ? C9 C10 C11 C12 1.1(3) . . . . ? C10 C11 C12 C13 -1.6(3) . . . . ? C11 C12 C13 C14 1.6(3) . . . . ? C10 C9 C14 C13 0.6(3) . . . . ? C4 C9 C14 C13 172.73(16) . . . . ? C12 C13 C14 C9 -1.1(3) . . . . ? C6 C1 C15 C16 80.37(18) . . . . ? C2 C1 C15 C16 -162.64(14) . . . . ? C7 C1 C15 C16 -43.8(2) . . . . ? C1 C15 C16 C17 -85.3(2) . . . . ? C1 C15 C16 C21 94.51(19) . . . . ? C21 C16 C17 C18 -0.8(2) . . . . ? C15 C16 C17 C18 179.05(16) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C17 C18 C19 C20 1.3(3) . . . . ? C18 C19 C20 C21 -0.8(3) . . . . ? C19 C20 C21 C16 -0.5(3) . . . . ? C17 C16 C21 C20 1.3(2) . . . . ? C15 C16 C21 C20 -178.57(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.237 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.046 #===END data_2g _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 N2 O2' _chemical_formula_weight 154.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7000(3) _cell_length_b 7.4300(2) _cell_length_c 9.9090(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.5650(13) _cell_angle_gamma 90.00 _cell_volume 711.89(4) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 1714 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 3100 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1631 _reflns_number_gt 1343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+0.2126P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1631 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.29113(13) 0.12932(17) 0.16111(13) 0.0147(3) Uani 1 1 d . . . H1 H 0.3155 0.2484 0.2036 0.018 Uiso 1 1 calc R . . O2 O 0.06935(10) 0.15366(13) 0.25971(10) 0.0206(3) Uani 1 1 d . . . C2 C 0.14789(13) 0.06696(18) 0.19257(13) 0.0147(3) Uani 1 1 d . . . N3 N 0.11929(11) -0.09510(15) 0.13760(11) 0.0147(3) Uani 1 1 d . . . H3 H 0.0393 -0.1488 0.1449 0.018 Uiso 1 1 calc R . . C4 C 0.22910(13) -0.17792(18) 0.06453(13) 0.0142(3) Uani 1 1 d . . . N5 N 0.35614(11) -0.17620(15) 0.15544(11) 0.0146(3) Uani 1 1 d . . . H5 H 0.4053 -0.2742 0.1729 0.018 Uiso 1 1 calc R . . O6 O 0.49668(9) 0.00683(13) 0.28962(10) 0.0187(3) Uani 1 1 d . . . C6 C 0.39291(13) -0.01720(17) 0.21010(13) 0.0139(3) Uani 1 1 d . . . C7 C 0.29131(14) 0.13610(19) 0.00406(14) 0.0180(3) Uani 1 1 d . . . H7A H 0.2229 0.2257 -0.0331 0.022 Uiso 1 1 calc R . . H7B H 0.3838 0.1726 -0.0217 0.022 Uiso 1 1 calc R . . C8 C 0.25423(14) -0.05220(19) -0.05460(13) 0.0172(3) Uani 1 1 d . . . H8A H 0.1700 -0.0450 -0.1177 0.021 Uiso 1 1 calc R . . H8B H 0.3309 -0.0988 -0.1048 0.021 Uiso 1 1 calc R . . C9 C 0.19124(14) -0.36855(19) 0.02285(15) 0.0187(3) Uani 1 1 d . . . H9A H 0.1716 -0.4384 0.1030 0.028 Uiso 1 1 calc R . . H9B H 0.2685 -0.4238 -0.0200 0.028 Uiso 1 1 calc R . . H9C H 0.1091 -0.3669 -0.0415 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0157(6) 0.0126(6) 0.0157(6) -0.0001(5) 0.0010(5) -0.0004(5) O2 0.0185(5) 0.0219(6) 0.0220(5) -0.0046(4) 0.0049(4) 0.0045(4) C2 0.0156(6) 0.0158(6) 0.0124(6) 0.0018(5) -0.0005(5) 0.0021(5) N3 0.0125(5) 0.0155(6) 0.0164(6) -0.0017(4) 0.0033(4) -0.0012(4) C4 0.0126(6) 0.0151(6) 0.0149(6) -0.0020(5) 0.0009(5) 0.0004(5) N5 0.0143(5) 0.0123(5) 0.0168(6) -0.0008(4) -0.0010(4) 0.0024(4) O6 0.0164(5) 0.0175(5) 0.0213(5) 0.0003(4) -0.0035(4) -0.0020(4) C6 0.0127(6) 0.0157(6) 0.0138(6) 0.0008(5) 0.0037(5) -0.0015(5) C7 0.0197(7) 0.0174(7) 0.0171(7) 0.0037(5) 0.0034(5) -0.0010(5) C8 0.0171(6) 0.0203(7) 0.0144(6) 0.0000(5) 0.0028(5) -0.0004(5) C9 0.0196(7) 0.0163(7) 0.0199(7) -0.0035(5) 0.0008(5) -0.0013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5203(18) . ? C1 C6 1.5229(18) . ? C1 C7 1.5571(19) . ? C1 H1 1.0000 . ? O2 C2 1.2324(16) . ? C2 N3 1.3414(17) . ? N3 C4 1.4697(16) . ? N3 H3 0.8800 . ? C4 N5 1.4675(16) . ? C4 C9 1.5124(18) . ? C4 C8 1.5399(19) . ? N5 C6 1.3362(16) . ? N5 H5 0.8800 . ? O6 C6 1.2408(16) . ? C7 C8 1.5464(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 107.25(10) . . ? C2 C1 C7 106.77(11) . . ? C6 C1 C7 106.83(11) . . ? C2 C1 H1 111.9 . . ? C6 C1 H1 111.9 . . ? C7 C1 H1 111.9 . . ? O2 C2 N3 124.87(12) . . ? O2 C2 C1 124.45(12) . . ? N3 C2 C1 110.68(11) . . ? C2 N3 C4 116.19(10) . . ? C2 N3 H3 121.9 . . ? C4 N3 H3 121.9 . . ? N5 C4 N3 107.46(10) . . ? N5 C4 C9 110.46(10) . . ? N3 C4 C9 110.91(11) . . ? N5 C4 C8 106.79(10) . . ? N3 C4 C8 106.78(10) . . ? C9 C4 C8 114.11(11) . . ? C6 N5 C4 116.14(11) . . ? C6 N5 H5 121.9 . . ? C4 N5 H5 121.9 . . ? O6 C6 N5 124.15(12) . . ? O6 C6 C1 124.90(11) . . ? N5 C6 C1 110.94(11) . . ? C8 C7 C1 109.13(11) . . ? C8 C7 H7A 109.9 . . ? C1 C7 H7A 109.9 . . ? C8 C7 H7B 109.9 . . ? C1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C4 C8 C7 107.88(11) . . ? C4 C8 H8A 110.1 . . ? C7 C8 H8A 110.1 . . ? C4 C8 H8B 110.1 . . ? C7 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O2 124.56(13) . . . . ? C7 C1 C2 O2 -121.23(14) . . . . ? C6 C1 C2 N3 -55.26(14) . . . . ? C7 C1 C2 N3 58.95(14) . . . . ? O2 C2 N3 C4 -178.24(12) . . . . ? C1 C2 N3 C4 1.58(15) . . . . ? C2 N3 C4 N5 52.09(14) . . . . ? C2 N3 C4 C9 172.93(11) . . . . ? C2 N3 C4 C8 -62.18(14) . . . . ? N3 C4 N5 C6 -52.48(14) . . . . ? C9 C4 N5 C6 -173.59(11) . . . . ? C8 C4 N5 C6 61.79(14) . . . . ? C4 N5 C6 O6 179.45(12) . . . . ? C4 N5 C6 C1 -0.86(15) . . . . ? C2 C1 C6 O6 -125.28(13) . . . . ? C7 C1 C6 O6 120.54(14) . . . . ? C2 C1 C6 N5 55.04(14) . . . . ? C7 C1 C6 N5 -59.14(13) . . . . ? C2 C1 C7 C8 -57.79(14) . . . . ? C6 C1 C7 C8 56.72(13) . . . . ? N5 C4 C8 C7 -57.75(13) . . . . ? N3 C4 C8 C7 56.97(13) . . . . ? C9 C4 C8 C7 179.89(11) . . . . ? C1 C7 C8 C4 0.55(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.289 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.054 #===END data_2h _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N2 O2' _chemical_formula_weight 168.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P nma' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 10.535(2) _cell_length_b 9.0614(18) _cell_length_c 8.4297(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 804.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 3663 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 4858 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.44 _reflns_number_total 973 _reflns_number_gt 740 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.0211P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 973 _refine_ls_number_parameters 66 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 1.574 _refine_ls_shift/su_mean 0.031 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.85476(10) 0.38114(12) 0.21539(13) 0.0131(3) Uani 1 1 d . . . H1 H 0.8420 0.4528 0.2840 0.016 Uiso 1 1 calc R . . O1 O 0.73793(9) 0.48408(11) 0.01483(11) 0.0170(3) Uani 1 1 d . . . C1 C 0.80614(12) 0.38554(15) 0.06784(16) 0.0124(3) Uani 1 1 d . . . C2 C 0.84725(18) 0.2500 -0.0287(2) 0.0136(5) Uani 1 2 d S . . C3 C 0.99539(19) 0.2500 -0.0284(2) 0.0170(5) Uani 1 2 d S . . H3A H 1.0270 0.1615 -0.0849 0.020 Uiso 0.50 1 calc PR . . H3B H 1.0270 0.3385 -0.0849 0.020 Uiso 0.50 1 calc PR . . C4 C 1.04553(19) 0.2500 0.1427(2) 0.0178(5) Uani 1 2 d S . . H4A H 1.0984 0.3386 0.1614 0.021 Uiso 0.50 1 calc PR . . H4B H 1.0984 0.1614 0.1614 0.021 Uiso 0.50 1 calc PR . . C5 C 0.93040(18) 0.2500 0.2557(2) 0.0133(5) Uani 1 2 d S . . C6 C 0.96441(19) 0.2500 0.4287(2) 0.0173(5) Uani 1 2 d S . . H6A H 1.0027 0.3450 0.4569 0.026 Uiso 0.50 1 calc PR . . H6B H 1.0251 0.1705 0.4500 0.026 Uiso 0.50 1 calc PR . . H6C H 0.8876 0.2345 0.4922 0.026 Uiso 0.50 1 calc PR . . C7 C 0.7913(2) 0.2500 -0.1938(2) 0.0186(5) Uani 1 2 d S . . H7A H 0.6985 0.2502 -0.1868 0.028 Uiso 1 2 calc SR . . H7B H 0.8195 0.1616 -0.2508 0.028 Uiso 0.50 1 calc PR . . H7C H 0.8198 0.3382 -0.2509 0.028 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0162(6) 0.0113(7) 0.0119(7) -0.0027(4) -0.0005(5) 0.0014(5) O1 0.0223(6) 0.0145(6) 0.0141(6) 0.0012(4) -0.0008(4) 0.0040(4) C1 0.0126(7) 0.0130(7) 0.0117(7) 0.0018(5) 0.0025(5) -0.0021(6) C2 0.0162(10) 0.0133(10) 0.0112(10) 0.000 0.0019(8) 0.000 C3 0.0185(11) 0.0160(11) 0.0164(11) 0.000 0.0059(8) 0.000 C4 0.0135(10) 0.0220(11) 0.0179(11) 0.000 0.0028(8) 0.000 C5 0.0124(9) 0.0142(10) 0.0134(10) 0.000 0.0004(8) 0.000 C6 0.0170(10) 0.0182(11) 0.0166(11) 0.000 -0.0028(8) 0.000 C7 0.0289(11) 0.0170(11) 0.0099(10) 0.000 0.0015(9) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3457(17) . ? N1 C5 1.4706(15) . ? N1 H1 0.8800 . ? O1 C1 1.2302(17) . ? C1 C2 1.5358(18) . ? C2 C7 1.511(3) . ? C2 C1 1.5358(18) 7_565 ? C2 C3 1.561(3) . ? C3 C4 1.536(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.542(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N1 1.4706(15) 7_565 ? C5 C6 1.502(3) . ? C6 H6A 0.9811 . ? C6 H6B 0.9811 . ? C6 H6C 0.9811 . ? C7 H7A 0.9803 . ? C7 H7B 0.9803 . ? C7 H7C 0.9803 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 116.34(12) . . ? C1 N1 H1 121.8 . . ? C5 N1 H1 121.8 . . ? O1 C1 N1 125.42(13) . . ? O1 C1 C2 123.55(13) . . ? N1 C1 C2 111.03(12) . . ? C7 C2 C1 112.22(11) . 7_565 ? C7 C2 C1 112.22(11) . . ? C1 C2 C1 106.20(15) 7_565 . ? C7 C2 C3 113.04(16) . . ? C1 C2 C3 106.33(11) 7_565 . ? C1 C2 C3 106.33(11) . . ? C4 C3 C2 110.22(16) . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 108.03(16) . . ? C3 C4 H4A 110.1 . . ? C5 C4 H4A 110.1 . . ? C3 C4 H4B 110.1 . . ? C5 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? N1 C5 N1 107.81(14) 7_565 . ? N1 C5 C6 110.71(10) 7_565 . ? N1 C5 C6 110.71(10) . . ? N1 C5 C4 106.47(10) 7_565 . ? N1 C5 C4 106.47(11) . . ? C6 C5 C4 114.35(17) . . ? C5 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 109.4 . . ? C5 C6 H6C 109.6 . . ? H6A C6 H6C 109.4 . . ? H6B C6 H6C 109.4 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.4 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.4 . . ? H7B C7 H7C 109.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 O1 177.91(13) . . . . ? C5 N1 C1 C2 -2.26(17) . . . . ? O1 C1 C2 C7 -1.6(2) . . . . ? N1 C1 C2 C7 178.57(12) . . . . ? O1 C1 C2 C1 -124.57(13) . . . 7_565 ? N1 C1 C2 C1 55.61(18) . . . 7_565 ? O1 C1 C2 C3 122.47(15) . . . . ? N1 C1 C2 C3 -57.36(15) . . . . ? C7 C2 C3 C4 180.0 . . . . ? C1 C2 C3 C4 -56.44(10) 7_565 . . . ? C1 C2 C3 C4 56.44(10) . . . . ? C2 C3 C4 C5 0.0 . . . . ? C1 N1 C5 N1 -51.46(18) . . . 7_565 ? C1 N1 C5 C6 -172.69(12) . . . . ? C1 N1 C5 C4 62.46(16) . . . . ? C3 C4 C5 N1 57.42(10) . . . 7_565 ? C3 C4 C5 N1 -57.42(10) . . . . ? C3 C4 C5 C6 180.0 . . . . ? _diffrn_measured_fraction_theta_max .998 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full .998 _refine_diff_density_max .287 _refine_diff_density_min -.293 _refine_diff_density_rms .058 #===END data_2i _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N2 O2' _chemical_formula_weight 230.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P nma' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 15.4460(6) _cell_length_b 9.9980(8) _cell_length_c 6.8770(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1062.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 6572 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 6968 _diffrn_reflns_av_R_equivalents 0.1166 _diffrn_reflns_av_sigmaI/netI 0.0987 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.43 _reflns_number_total 1276 _reflns_number_gt 768 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1276 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1023 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _refine_ls_shift/su_max 0.247 _refine_ls_shift/su_mean 0.005 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.26095(17) 0.2500 0.2985(4) 0.0136(6) Uani 1 2 d S . . O2 O 0.20400(8) 0.03581(13) 0.18140(18) 0.0187(4) Uani 1 1 d . . . C2 C 0.25748(12) 0.12745(19) 0.1656(3) 0.0142(5) Uani 1 1 d . . . N3 N 0.31936(9) 0.13172(15) 0.0274(2) 0.0146(4) Uani 1 1 d . . . H3 H 0.3256 0.0676 -0.0592 0.017 Uiso 1 1 calc R . . C4 C 0.37564(17) 0.2500 0.0302(4) 0.0143(6) Uani 1 2 d S . . C5 C 0.35260(16) 0.2500 0.3908(4) 0.0160(7) Uani 1 2 d S . . H5A H 0.3597 0.3302 0.4737 0.019 Uiso 0.50 1 calc PR . . H5B H 0.3597 0.1698 0.4737 0.019 Uiso 0.50 1 calc PR . . C6 C 0.42202(17) 0.2500 0.2296(3) 0.0173(7) Uani 1 2 d S . . H6A H 0.4591 0.1697 0.2417 0.021 Uiso 0.50 1 calc PR . . H6B H 0.4591 0.3303 0.2417 0.021 Uiso 0.50 1 calc PR . . C7 C 0.44183(17) 0.2500 -0.1323(4) 0.0143(6) Uani 1 2 d S . . C8 C 0.47599(12) 0.37022(19) -0.2003(3) 0.0167(5) Uani 1 1 d . . . H8 H 0.4540 0.4527 -0.1529 0.020 Uiso 1 1 calc R . . C9 C 0.54217(12) 0.36973(19) -0.3372(3) 0.0186(5) Uani 1 1 d . . . H9 H 0.5649 0.4519 -0.3841 0.022 Uiso 1 1 calc R . . C10 C 0.57495(17) 0.2500 -0.4053(4) 0.0181(7) Uani 1 2 d S . . H10 H 0.6201 0.2500 -0.4991 0.022 Uiso 1 2 calc SR . . C11 C 0.18995(17) 0.2500 0.4509(4) 0.0195(7) Uani 1 2 d S . . H11A H 0.1333 0.2482 0.3866 0.029 Uiso 1 2 calc SR . . H11B H 0.1946 0.3309 0.5306 0.029 Uiso 0.50 1 calc PR . . H11C H 0.1960 0.1709 0.5339 0.029 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0164(15) 0.0117(14) 0.0127(15) 0.000 0.0010(12) 0.000 O2 0.0201(8) 0.0153(7) 0.0205(9) 0.0009(6) 0.0000(6) -0.0031(6) C2 0.0153(11) 0.0132(11) 0.0141(11) 0.0040(9) -0.0033(8) 0.0002(9) N3 0.0188(9) 0.0100(8) 0.0149(9) -0.0044(7) 0.0031(7) -0.0039(8) C4 0.0166(15) 0.0103(14) 0.0160(16) 0.000 0.0023(12) 0.000 C5 0.0215(16) 0.0121(15) 0.0143(16) 0.000 -0.0034(12) 0.000 C6 0.0167(16) 0.0164(15) 0.0188(17) 0.000 -0.0010(12) 0.000 C7 0.0156(15) 0.0146(15) 0.0126(15) 0.000 -0.0038(11) 0.000 C8 0.0178(11) 0.0150(11) 0.0175(11) -0.0008(9) -0.0010(9) 0.0030(9) C9 0.0188(11) 0.0162(11) 0.0209(12) 0.0029(9) -0.0009(9) -0.0025(9) C10 0.0163(15) 0.0212(17) 0.0168(16) 0.000 0.0022(12) 0.000 C11 0.0243(16) 0.0154(16) 0.0189(17) 0.000 0.0045(13) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C11 1.517(3) . ? C1 C2 1.529(2) . ? C1 C2 1.529(2) 8_565 ? C1 C5 1.551(3) . ? O2 C2 1.238(2) . ? C2 N3 1.349(2) . ? N3 C4 1.468(2) . ? N3 H3 0.8800 . ? C4 N3 1.468(2) 8_565 ? C4 C7 1.515(3) . ? C4 C6 1.547(3) . ? C5 C6 1.542(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.393(2) . ? C7 C8 1.393(2) 8_565 ? C8 C9 1.390(2) . ? C8 H8 0.9500 . ? C9 C10 1.382(2) . ? C9 H9 0.9500 . ? C10 C9 1.382(2) 8_565 ? C10 H10 0.9500 . ? C11 H11A 0.9801 . ? C11 H11B 0.9801 . ? C11 H11C 0.9801 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 C1 C2 112.79(14) . . ? C11 C1 C2 112.79(14) . 8_565 ? C2 C1 C2 106.5(2) . 8_565 ? C11 C1 C5 112.1(2) . . ? C2 C1 C5 106.04(14) . . ? C2 C1 C5 106.04(15) 8_565 . ? O2 C2 N3 123.90(17) . . ? O2 C2 C1 124.32(18) . . ? N3 C2 C1 111.77(17) . . ? C2 N3 C4 115.82(16) . . ? C2 N3 H3 122.1 . . ? C4 N3 H3 122.1 . . ? N3 C4 N3 107.4(2) 8_565 . ? N3 C4 C7 112.94(13) 8_565 . ? N3 C4 C7 112.94(13) . . ? N3 C4 C6 106.63(14) 8_565 . ? N3 C4 C6 106.63(14) . . ? C7 C4 C6 110.0(2) . . ? C6 C5 C1 109.9(2) . . ? C6 C5 H5A 109.7 . . ? C1 C5 H5A 109.7 . . ? C6 C5 H5B 109.7 . . ? C1 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C5 C6 C4 108.4(2) . . ? C5 C6 H6A 110.0 . . ? C4 C6 H6A 110.0 . . ? C5 C6 H6B 110.0 . . ? C4 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? C8 C7 C8 119.2(2) . 8_565 ? C8 C7 C4 120.20(12) . . ? C8 C7 C4 120.20(12) 8_565 . ? C9 C8 C7 120.17(19) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C9 120.1(3) 8_565 . ? C9 C10 H10 120.0 8_565 . ? C9 C10 H10 120.0 . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 C1 C2 O2 -1.4(3) . . . . ? C2 C1 C2 O2 -125.66(17) 8_565 . . . ? C5 C1 C2 O2 121.7(2) . . . . ? C11 C1 C2 N3 177.96(16) . . . . ? C2 C1 C2 N3 53.7(2) 8_565 . . . ? C5 C1 C2 N3 -58.9(2) . . . . ? O2 C2 N3 C4 178.86(18) . . . . ? C1 C2 N3 C4 -0.5(2) . . . . ? C2 N3 C4 N3 -53.2(2) . . . 8_565 ? C2 N3 C4 C7 -178.35(16) . . . . ? C2 N3 C4 C6 60.8(2) . . . . ? C11 C1 C5 C6 180.0 . . . . ? C2 C1 C5 C6 56.48(13) . . . . ? C2 C1 C5 C6 -56.48(13) 8_565 . . . ? C1 C5 C6 C4 0.0 . . . . ? N3 C4 C6 C5 57.23(13) 8_565 . . . ? N3 C4 C6 C5 -57.23(13) . . . . ? C7 C4 C6 C5 180.0 . . . . ? N3 C4 C7 C8 32.5(3) 8_565 . . . ? N3 C4 C7 C8 154.55(19) . . . . ? C6 C4 C7 C8 -86.5(2) . . . . ? N3 C4 C7 C8 -154.55(19) 8_565 . . 8_565 ? N3 C4 C7 C8 -32.5(3) . . . 8_565 ? C6 C4 C7 C8 86.5(2) . . . 8_565 ? C8 C7 C8 C9 1.3(4) 8_565 . . . ? C4 C7 C8 C9 174.3(2) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C8 C9 C10 C9 -0.1(4) . . . 8_565 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.272 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.062 #===END data_2j _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O2' _chemical_formula_weight 244.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6270(5) _cell_length_b 9.5935(5) _cell_length_c 12.1741(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.990(2) _cell_angle_gamma 90.00 _cell_volume 1199.10(9) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 9718 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 7200 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2109 _reflns_number_gt 1657 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+0.2955P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0093(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2109 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.11763(10) 0.12232(12) 0.10876(10) 0.0152(3) Uani 1 1 d . . . C1 C 0.28628(15) 0.18073(18) 0.04789(15) 0.0119(4) Uani 1 1 d . . . C2 C 0.15651(16) 0.11944(17) 0.02935(15) 0.0120(4) Uani 1 1 d . . . N3 N 0.08958(13) 0.06108(14) -0.08262(11) 0.0133(4) Uani 1 1 d . . . H3 H 0.0147 0.0188 -0.1048 0.016 Uiso 1 1 calc R . . C4 C 0.14721(16) 0.07099(18) -0.16694(14) 0.0135(4) Uani 1 1 d . . . N5 N 0.17708(13) 0.21832(14) -0.17045(12) 0.0140(4) Uani 1 1 d . . . H5 H 0.1479 0.2636 -0.2414 0.017 Uiso 1 1 calc R . . O6 O 0.28607(11) 0.40430(13) -0.04916(10) 0.0190(3) Uani 1 1 d . . . C6 C 0.25101(15) 0.28247(19) -0.06096(15) 0.0134(4) Uani 1 1 d . . . C7 C 0.36008(16) 0.05740(18) 0.02462(14) 0.0141(4) Uani 1 1 d . . . H7A H 0.4428 0.0920 0.0300 0.017 Uiso 1 1 calc R . . H7B H 0.3815 -0.0143 0.0899 0.017 Uiso 1 1 calc R . . C8 C 0.27668(15) -0.00846(18) -0.10414(15) 0.0147(4) Uani 1 1 d . . . H8A H 0.3223 -0.0017 -0.1551 0.018 Uiso 1 1 calc R . . H8B H 0.2608 -0.1081 -0.0951 0.018 Uiso 1 1 calc R . . C9 C 0.05181(16) 0.01991(19) -0.29523(15) 0.0178(4) Uani 1 1 d . . . H9A H -0.0278 0.0761 -0.3275 0.027 Uiso 1 1 calc R . . H9B H 0.0305 -0.0780 -0.2905 0.027 Uiso 1 1 calc R . . H9C H 0.0909 0.0285 -0.3508 0.027 Uiso 1 1 calc R . . C10 C 0.36129(15) 0.24877(19) 0.17598(14) 0.0154(4) Uani 1 1 d . . . H10A H 0.3284 0.3451 0.1701 0.018 Uiso 1 1 calc R . . H10B H 0.3399 0.1976 0.2347 0.018 Uiso 1 1 calc R . . C11 C 0.50837(16) 0.25557(18) 0.23204(15) 0.0132(4) Uani 1 1 d . . . C12 C 0.57160(17) 0.33652(17) 0.18131(15) 0.0144(4) Uani 1 1 d . . . H12 H 0.5216 0.3855 0.1058 0.017 Uiso 1 1 calc R . . C13 C 0.70598(16) 0.34636(19) 0.23954(15) 0.0164(4) Uani 1 1 d . . . H13 H 0.7474 0.4027 0.2043 0.020 Uiso 1 1 calc R . . C14 C 0.78057(16) 0.27433(18) 0.34925(15) 0.0176(4) Uani 1 1 d . . . H14 H 0.8728 0.2819 0.3897 0.021 Uiso 1 1 calc R . . C15 C 0.71945(16) 0.19136(19) 0.39917(16) 0.0186(5) Uani 1 1 d . . . H15 H 0.7699 0.1401 0.4732 0.022 Uiso 1 1 calc R . . C16 C 0.58474(16) 0.18291(18) 0.34135(15) 0.0162(4) Uani 1 1 d . . . H16 H 0.5438 0.1265 0.3770 0.019 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0148(7) 0.0189(7) 0.0144(6) -0.0014(5) 0.0089(5) -0.0013(5) C1 0.0099(9) 0.0134(10) 0.0129(9) -0.0003(7) 0.0056(7) 0.0004(8) C2 0.0117(9) 0.0113(10) 0.0127(9) 0.0038(7) 0.0055(8) 0.0042(8) N3 0.0081(7) 0.0184(9) 0.0122(8) -0.0027(6) 0.0038(6) -0.0035(6) C4 0.0144(9) 0.0157(10) 0.0124(9) -0.0009(7) 0.0080(8) -0.0007(8) N5 0.0152(8) 0.0142(9) 0.0103(8) 0.0032(6) 0.0041(6) 0.0009(7) O6 0.0213(7) 0.0129(8) 0.0213(7) 0.0009(5) 0.0087(6) -0.0023(6) C6 0.0090(9) 0.0160(11) 0.0175(10) 0.0002(8) 0.0081(8) 0.0014(8) C7 0.0120(9) 0.0157(10) 0.0140(9) 0.0020(7) 0.0056(7) 0.0012(8) C8 0.0140(10) 0.0151(10) 0.0163(9) -0.0007(7) 0.0082(8) 0.0008(8) C9 0.0156(10) 0.0213(11) 0.0167(10) -0.0016(8) 0.0077(8) -0.0008(8) C10 0.0147(10) 0.0175(10) 0.0142(9) -0.0025(8) 0.0070(8) -0.0014(8) C11 0.0135(9) 0.0119(9) 0.0129(9) -0.0040(7) 0.0052(8) -0.0008(8) C12 0.0178(10) 0.0116(10) 0.0127(9) -0.0006(7) 0.0062(8) 0.0013(8) C13 0.0178(10) 0.0148(11) 0.0206(10) -0.0047(8) 0.0125(8) -0.0047(8) C14 0.0112(10) 0.0174(11) 0.0219(10) -0.0055(8) 0.0058(8) -0.0020(8) C15 0.0171(10) 0.0155(11) 0.0156(9) 0.0011(8) 0.0013(8) 0.0006(8) C16 0.0172(10) 0.0149(10) 0.0158(9) -0.0016(8) 0.0073(8) -0.0047(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.2450(19) . ? C1 C10 1.530(2) . ? C1 C2 1.534(2) . ? C1 C6 1.538(2) . ? C1 C7 1.564(2) . ? C2 N3 1.335(2) . ? N3 C4 1.469(2) . ? N3 H3 0.8800 . ? C4 N5 1.461(2) . ? C4 C9 1.511(2) . ? C4 C8 1.533(2) . ? N5 C6 1.349(2) . ? N5 H5 0.8800 . ? O6 C6 1.224(2) . ? C7 C8 1.539(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.516(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.391(2) . ? C11 C12 1.397(2) . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 C15 1.383(2) . ? C14 H14 0.9500 . ? C15 C16 1.386(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C1 C2 111.36(13) . . ? C10 C1 C6 113.65(14) . . ? C2 C1 C6 105.68(13) . . ? C10 C1 C7 114.12(13) . . ? C2 C1 C7 105.59(13) . . ? C6 C1 C7 105.73(13) . . ? O1 C2 N3 123.52(15) . . ? O1 C2 C1 124.59(14) . . ? N3 C2 C1 111.89(14) . . ? C2 N3 C4 116.62(13) . . ? C2 N3 H3 121.7 . . ? C4 N3 H3 121.7 . . ? N5 C4 N3 106.01(13) . . ? N5 C4 C9 110.66(14) . . ? N3 C4 C9 110.30(13) . . ? N5 C4 C8 107.71(13) . . ? N3 C4 C8 106.41(13) . . ? C9 C4 C8 115.27(14) . . ? C6 N5 C4 117.56(13) . . ? C6 N5 H5 121.2 . . ? C4 N5 H5 121.2 . . ? O6 C6 N5 125.06(15) . . ? O6 C6 C1 124.43(14) . . ? N5 C6 C1 110.51(14) . . ? C8 C7 C1 110.99(13) . . ? C8 C7 H7A 109.4 . . ? C1 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C1 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C4 C8 C7 107.79(13) . . ? C4 C8 H8A 110.1 . . ? C7 C8 H8A 110.1 . . ? C4 C8 H8B 110.1 . . ? C7 C8 H8B 110.1 . . ? H8A C8 H8B 108.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C1 117.38(14) . . ? C11 C10 H10A 108.0 . . ? C1 C10 H10A 108.0 . . ? C11 C10 H10B 108.0 . . ? C1 C10 H10B 108.0 . . ? H10A C10 H10B 107.2 . . ? C16 C11 C12 117.99(15) . . ? C16 C11 C10 119.18(15) . . ? C12 C11 C10 122.78(15) . . ? C13 C12 C11 120.91(16) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.30(16) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 119.44(16) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 120.12(16) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 121.21(17) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 O1 -1.1(2) . . . . ? C6 C1 C2 O1 -124.96(17) . . . . ? C7 C1 C2 O1 123.28(16) . . . . ? C10 C1 C2 N3 179.34(14) . . . . ? C6 C1 C2 N3 55.48(17) . . . . ? C7 C1 C2 N3 -56.28(17) . . . . ? O1 C2 N3 C4 177.92(15) . . . . ? C1 C2 N3 C4 -2.5(2) . . . . ? C2 N3 C4 N5 -51.73(18) . . . . ? C2 N3 C4 C9 -171.56(14) . . . . ? C2 N3 C4 C8 62.75(18) . . . . ? N3 C4 N5 C6 54.03(18) . . . . ? C9 C4 N5 C6 173.63(14) . . . . ? C8 C4 N5 C6 -59.55(18) . . . . ? C4 N5 C6 O6 178.53(15) . . . . ? C4 N5 C6 C1 -1.1(2) . . . . ? C10 C1 C6 O6 4.9(2) . . . . ? C2 C1 C6 O6 127.27(17) . . . . ? C7 C1 C6 O6 -121.07(17) . . . . ? C10 C1 C6 N5 -175.48(13) . . . . ? C2 C1 C6 N5 -53.08(17) . . . . ? C7 C1 C6 N5 58.58(16) . . . . ? C10 C1 C7 C8 178.13(14) . . . . ? C2 C1 C7 C8 55.50(17) . . . . ? C6 C1 C7 C8 -56.22(17) . . . . ? N5 C4 C8 C7 56.16(16) . . . . ? N3 C4 C8 C7 -57.15(17) . . . . ? C9 C4 C8 C7 -179.76(14) . . . . ? C1 C7 C8 C4 0.06(18) . . . . ? C2 C1 C10 C11 153.30(15) . . . . ? C6 C1 C10 C11 -87.48(19) . . . . ? C7 C1 C10 C11 33.9(2) . . . . ? C1 C10 C11 C16 -115.95(17) . . . . ? C1 C10 C11 C12 66.6(2) . . . . ? C16 C11 C12 C13 -1.4(2) . . . . ? C10 C11 C12 C13 176.07(16) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C13 C14 C15 C16 -1.4(3) . . . . ? C14 C15 C16 C11 0.7(3) . . . . ? C12 C11 C16 C15 0.6(2) . . . . ? C10 C11 C16 C15 -176.89(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max .224 _refine_diff_density_min -.208 _refine_diff_density_rms .043 #===END data_2k _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O2' _chemical_formula_weight 244.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5250(3) _cell_length_b 10.6020(3) _cell_length_c 11.5520(3) _cell_angle_alpha 98.2850(11) _cell_angle_beta 91.3030(11) _cell_angle_gamma 109.8320(12) _cell_volume 1196.38(6) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 4911 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\w scans at fixed \c = 55\%' _diffrn_detector_area_resol_mean 18 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 9294 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.1028 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5483 _reflns_number_gt 3222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material ; SHELX97-2 (Sheldrick, 1997) and local procedures ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0057(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5483 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1A C 0.51361(18) 0.08416(18) 0.81783(16) 0.0136(4) Uani 1 1 d . . . O2A O 0.40126(12) -0.16429(12) 0.78799(10) 0.0165(3) Uani 1 1 d . . . C2A C 0.49861(19) -0.06468(19) 0.77200(16) 0.0139(4) Uani 1 1 d . . . N3A N 0.60662(15) -0.07151(15) 0.71628(13) 0.0148(4) Uani 1 1 d . . . H3A H 0.6110 -0.1499 0.6831 0.018 Uiso 1 1 calc R . . C4A C 0.71765(19) 0.05678(18) 0.71265(16) 0.0149(4) Uani 1 1 d . . . N5A N 0.65814(15) 0.14515(15) 0.66357(13) 0.0162(4) Uani 1 1 d . . . H5A H 0.6917 0.1856 0.6041 0.019 Uiso 1 1 calc R . . O6A O 0.48909(13) 0.23334(13) 0.68166(11) 0.0194(3) Uani 1 1 d . . . C6A C 0.54985(19) 0.16190(18) 0.71337(16) 0.0141(4) Uani 1 1 d . . . C7A C 0.64567(18) 0.14203(19) 0.90322(16) 0.0169(5) Uani 1 1 d . . . H7A1 H 0.6657 0.2401 0.9308 0.020 Uiso 1 1 calc R . . H7A2 H 0.6314 0.0952 0.9725 0.020 Uiso 1 1 calc R . . C8A C 0.76635(19) 0.12147(19) 0.84073(16) 0.0179(5) Uani 1 1 d . . . H8A1 H 0.8403 0.2099 0.8438 0.021 Uiso 1 1 calc R . . H8A2 H 0.8013 0.0615 0.8800 0.021 Uiso 1 1 calc R . . C9A C 0.82870(19) 0.03315(19) 0.64066(16) 0.0171(5) Uani 1 1 d . . . H9A1 H 0.8544 -0.0393 0.6691 0.020 Uiso 1 1 calc R . . H9A2 H 0.9093 0.1173 0.6545 0.020 Uiso 1 1 calc R . . C10A C 0.7912(2) -0.0070(2) 0.50905(17) 0.0210(5) Uani 1 1 d . . . H10A H 0.7082 -0.0870 0.4943 0.032 Uiso 1 1 calc R . . H10B H 0.8650 -0.0282 0.4703 0.032 Uiso 1 1 calc R . . H10C H 0.7762 0.0685 0.4779 0.032 Uiso 1 1 calc R . . C11A C 0.38822(19) 0.09979(18) 0.87182(16) 0.0151(4) Uani 1 1 d . . . C12A C 0.3941(2) 0.17442(18) 0.98196(16) 0.0171(5) Uani 1 1 d . . . H12A H 0.4784 0.2141 1.0275 0.020 Uiso 1 1 calc R . . C13A C 0.2790(2) 0.19228(19) 1.02690(17) 0.0207(5) Uani 1 1 d . . . H13A H 0.2854 0.2451 1.1020 0.025 Uiso 1 1 calc R . . C14A C 0.1556(2) 0.1337(2) 0.96288(18) 0.0234(5) Uani 1 1 d . . . H14A H 0.0767 0.1456 0.9935 0.028 Uiso 1 1 calc R . . C15A C 0.1478(2) 0.0573(2) 0.85356(18) 0.0222(5) Uani 1 1 d . . . H15A H 0.0628 0.0159 0.8093 0.027 Uiso 1 1 calc R . . C16A C 0.2625(2) 0.04063(19) 0.80807(17) 0.0188(5) Uani 1 1 d . . . H16A H 0.2557 -0.0117 0.7326 0.023 Uiso 1 1 calc R . . C1B C 0.81028(18) 0.57534(18) 0.53709(16) 0.0131(4) Uani 1 1 d . . . O2B O 0.77410(13) 0.33033(12) 0.50727(11) 0.0168(3) Uani 1 1 d . . . C2B C 0.75792(18) 0.42810(19) 0.47019(16) 0.0136(4) Uani 1 1 d . . . N3B N 0.69688(15) 0.42142(15) 0.36585(13) 0.0150(4) Uani 1 1 d . . . H3B H 0.6623 0.3437 0.3178 0.018 Uiso 1 1 calc R . . C4B C 0.68920(19) 0.54730(18) 0.33387(16) 0.0141(4) Uani 1 1 d . . . N5B N 0.63022(15) 0.60825(15) 0.43112(13) 0.0152(4) Uani 1 1 d . . . H5B H 0.5583 0.6306 0.4190 0.018 Uiso 1 1 calc R . . O6B O 0.66103(13) 0.68863(13) 0.62841(11) 0.0177(3) Uani 1 1 d . . . C6B C 0.69055(19) 0.62852(18) 0.53933(17) 0.0147(4) Uani 1 1 d . . . C7B C 0.90771(19) 0.66249(19) 0.45496(16) 0.0170(5) Uani 1 1 d . . . H7B1 H 0.9382 0.7597 0.4904 0.020 Uiso 1 1 calc R . . H7B2 H 0.9887 0.6353 0.4473 0.020 Uiso 1 1 calc R . . C8B C 0.83606(19) 0.64301(19) 0.33271(16) 0.0169(5) Uani 1 1 d . . . H8B1 H 0.8374 0.7317 0.3140 0.020 Uiso 1 1 calc R . . H8B2 H 0.8830 0.6033 0.2724 0.020 Uiso 1 1 calc R . . C9B C 0.6015(2) 0.5201(2) 0.22017(16) 0.0184(5) Uani 1 1 d . . . H9B1 H 0.5790 0.6021 0.2125 0.022 Uiso 1 1 calc R . . H9B2 H 0.5156 0.4450 0.2245 0.022 Uiso 1 1 calc R . . C10B C 0.6685(2) 0.4832(2) 0.11098(16) 0.0213(5) Uani 1 1 d . . . H10D H 0.7490 0.5606 0.1016 0.032 Uiso 1 1 calc R . . H10E H 0.6045 0.4607 0.0419 0.032 Uiso 1 1 calc R . . H10F H 0.6951 0.4047 0.1193 0.032 Uiso 1 1 calc R . . C11B C 0.87333(19) 0.58697(18) 0.65900(16) 0.0138(4) Uani 1 1 d . . . C12B C 1.00531(19) 0.67220(19) 0.69589(16) 0.0158(4) Uani 1 1 d . . . H12B H 1.0592 0.7247 0.6431 0.019 Uiso 1 1 calc R . . C13B C 1.05924(19) 0.68131(19) 0.80924(17) 0.0182(5) Uani 1 1 d . . . H13B H 1.1493 0.7402 0.8335 0.022 Uiso 1 1 calc R . . C14B C 0.9821(2) 0.60492(19) 0.88635(17) 0.0187(5) Uani 1 1 d . . . H14B H 1.0188 0.6110 0.9637 0.022 Uiso 1 1 calc R . . C15B C 0.8511(2) 0.51958(19) 0.85070(17) 0.0199(5) Uani 1 1 d . . . H15B H 0.7981 0.4666 0.9037 0.024 Uiso 1 1 calc R . . C16B C 0.79658(19) 0.51073(19) 0.73879(16) 0.0160(4) Uani 1 1 d . . . H16B H 0.7061 0.4523 0.7156 0.019 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0155(11) 0.0122(10) 0.0134(10) 0.0022(8) 0.0007(8) 0.0052(8) O2A 0.0176(8) 0.0129(7) 0.0165(8) 0.0019(6) 0.0019(6) 0.0020(6) C2A 0.0172(11) 0.0152(10) 0.0108(10) 0.0016(8) -0.0011(8) 0.0079(9) N3A 0.0172(9) 0.0095(8) 0.0183(9) 0.0009(7) 0.0030(7) 0.0058(7) C4A 0.0169(11) 0.0138(10) 0.0142(11) 0.0028(8) 0.0008(8) 0.0050(9) N5A 0.0204(10) 0.0174(9) 0.0147(9) 0.0072(7) 0.0051(7) 0.0094(8) O6A 0.0223(8) 0.0181(7) 0.0212(8) 0.0062(6) 0.0020(6) 0.0101(6) C6A 0.0153(11) 0.0099(10) 0.0146(11) -0.0013(8) -0.0003(8) 0.0026(8) C7A 0.0203(11) 0.0152(10) 0.0142(11) 0.0019(8) 0.0011(9) 0.0051(9) C8A 0.0187(11) 0.0182(11) 0.0169(11) 0.0028(9) 0.0004(9) 0.0068(9) C9A 0.0176(11) 0.0140(10) 0.0204(11) 0.0037(8) 0.0038(9) 0.0059(9) C10A 0.0229(12) 0.0213(11) 0.0208(12) 0.0042(9) 0.0054(9) 0.0096(10) C11A 0.0185(11) 0.0126(10) 0.0160(11) 0.0058(8) 0.0032(9) 0.0061(9) C12A 0.0190(11) 0.0129(10) 0.0182(11) 0.0037(9) 0.0009(9) 0.0037(9) C13A 0.0276(13) 0.0169(11) 0.0187(11) 0.0012(9) 0.0060(10) 0.0098(10) C14A 0.0236(12) 0.0228(12) 0.0295(13) 0.0082(10) 0.0108(10) 0.0132(10) C15A 0.0190(12) 0.0245(12) 0.0245(12) 0.0057(10) 0.0013(9) 0.0087(10) C16A 0.0219(12) 0.0193(11) 0.0151(11) 0.0016(9) 0.0000(9) 0.0078(9) C1B 0.0133(10) 0.0139(10) 0.0132(10) 0.0040(8) 0.0042(8) 0.0053(8) O2B 0.0215(8) 0.0127(7) 0.0189(8) 0.0049(6) 0.0046(6) 0.0083(6) C2B 0.0117(10) 0.0147(10) 0.0149(11) 0.0024(8) 0.0048(8) 0.0052(8) N3B 0.0188(9) 0.0095(8) 0.0154(9) -0.0007(7) -0.0015(7) 0.0045(7) C4B 0.0179(11) 0.0110(10) 0.0138(10) 0.0010(8) 0.0010(8) 0.0058(8) N5B 0.0165(9) 0.0185(9) 0.0143(9) 0.0031(7) 0.0017(7) 0.0105(7) O6B 0.0217(8) 0.0154(7) 0.0176(8) 0.0003(6) 0.0039(6) 0.0093(6) C6B 0.0145(11) 0.0096(10) 0.0183(12) 0.0024(8) 0.0017(9) 0.0019(8) C7B 0.0171(11) 0.0154(10) 0.0176(11) 0.0039(8) 0.0046(8) 0.0040(9) C8B 0.0203(11) 0.0162(11) 0.0145(11) 0.0035(8) 0.0031(9) 0.0062(9) C9B 0.0220(11) 0.0172(11) 0.0171(11) 0.0024(8) 0.0003(9) 0.0084(9) C10B 0.0249(12) 0.0203(11) 0.0174(11) 0.0018(9) 0.0007(9) 0.0067(10) C11B 0.0169(11) 0.0106(10) 0.0158(11) 0.0013(8) 0.0032(8) 0.0075(9) C12B 0.0165(11) 0.0147(10) 0.0169(11) 0.0037(8) 0.0041(9) 0.0056(9) C13B 0.0152(11) 0.0195(11) 0.0190(12) 0.0007(9) -0.0020(9) 0.0060(9) C14B 0.0253(12) 0.0195(11) 0.0120(11) 0.0000(9) -0.0030(9) 0.0102(10) C15B 0.0285(13) 0.0166(11) 0.0152(11) 0.0041(9) 0.0036(9) 0.0078(10) C16B 0.0155(11) 0.0134(10) 0.0177(11) 0.0012(8) 0.0012(9) 0.0040(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A C11A 1.521(3) . ? C1A C6A 1.541(3) . ? C1A C2A 1.543(3) . ? C1A C7A 1.570(3) . ? O2A C2A 1.237(2) . ? C2A N3A 1.337(2) . ? N3A C4A 1.469(2) . ? N3A H3A 0.8800 . ? C4A N5A 1.458(2) . ? C4A C9A 1.518(2) . ? C4A C8A 1.535(2) . ? N5A C6A 1.341(2) . ? N5A H5A 0.8800 . ? O6A C6A 1.231(2) . ? C7A C8A 1.538(2) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A C10A 1.523(3) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? C11A C12A 1.386(3) . ? C11A C16A 1.395(3) . ? C12A C13A 1.389(3) . ? C12A H12A 0.9500 . ? C13A C14A 1.377(3) . ? C13A H13A 0.9500 . ? C14A C15A 1.383(3) . ? C14A H14A 0.9500 . ? C15A C16A 1.383(3) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C1B C11B 1.513(3) . ? C1B C2B 1.545(2) . ? C1B C6B 1.545(3) . ? C1B C7B 1.568(2) . ? O2B C2B 1.238(2) . ? C2B N3B 1.334(2) . ? N3B C4B 1.462(2) . ? N3B H3B 0.8800 . ? C4B N5B 1.470(2) . ? C4B C9B 1.521(3) . ? C4B C8B 1.536(3) . ? N5B C6B 1.344(2) . ? N5B H5B 0.8800 . ? O6B C6B 1.233(2) . ? C7B C8B 1.539(3) . ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9B C10B 1.525(2) . ? C9B H9B1 0.9900 . ? C9B H9B2 0.9900 . ? C10B H10D 0.9800 . ? C10B H10E 0.9800 . ? C10B H10F 0.9800 . ? C11B C12B 1.392(3) . ? C11B C16B 1.400(2) . ? C12B C13B 1.392(3) . ? C12B H12B 0.9500 . ? C13B C14B 1.380(3) . ? C13B H13B 0.9500 . ? C14B C15B 1.382(3) . ? C14B H14B 0.9500 . ? C15B C16B 1.380(3) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11A C1A C6A 111.48(15) . . ? C11A C1A C2A 113.61(15) . . ? C6A C1A C2A 106.74(14) . . ? C11A C1A C7A 114.47(15) . . ? C6A C1A C7A 104.44(14) . . ? C2A C1A C7A 105.35(15) . . ? O2A C2A N3A 124.67(17) . . ? O2A C2A C1A 124.28(16) . . ? N3A C2A C1A 111.01(16) . . ? C2A N3A C4A 117.44(15) . . ? C2A N3A H3A 121.3 . . ? C4A N3A H3A 121.3 . . ? N5A C4A N3A 106.69(15) . . ? N5A C4A C9A 111.89(15) . . ? N3A C4A C9A 111.16(15) . . ? N5A C4A C8A 106.89(15) . . ? N3A C4A C8A 106.40(14) . . ? C9A C4A C8A 113.41(16) . . ? C6A N5A C4A 116.88(15) . . ? C6A N5A H5A 121.6 . . ? C4A N5A H5A 121.6 . . ? O6A C6A N5A 124.26(17) . . ? O6A C6A C1A 124.12(16) . . ? N5A C6A C1A 111.59(16) . . ? C8A C7A C1A 110.53(14) . . ? C8A C7A H7A1 109.5 . . ? C1A C7A H7A1 109.5 . . ? C8A C7A H7A2 109.5 . . ? C1A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 108.1 . . ? C4A C8A C7A 108.28(15) . . ? C4A C8A H8A1 110.0 . . ? C7A C8A H8A1 110.0 . . ? C4A C8A H8A2 110.0 . . ? C7A C8A H8A2 110.0 . . ? H8A1 C8A H8A2 108.4 . . ? C4A C9A C10A 114.84(16) . . ? C4A C9A H9A1 108.6 . . ? C10A C9A H9A1 108.6 . . ? C4A C9A H9A2 108.6 . . ? C10A C9A H9A2 108.6 . . ? H9A1 C9A H9A2 107.5 . . ? C9A C10A H10A 109.5 . . ? C9A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C9A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C12A C11A C16A 118.04(18) . . ? C12A C11A C1A 122.37(17) . . ? C16A C11A C1A 119.56(17) . . ? C11A C12A C13A 121.17(19) . . ? C11A C12A H12A 119.4 . . ? C13A C12A H12A 119.4 . . ? C14A C13A C12A 120.19(18) . . ? C14A C13A H13A 119.9 . . ? C12A C13A H13A 119.9 . . ? C13A C14A C15A 119.30(19) . . ? C13A C14A H14A 120.3 . . ? C15A C14A H14A 120.3 . . ? C16A C15A C14A 120.6(2) . . ? C16A C15A H15A 119.7 . . ? C14A C15A H15A 119.7 . . ? C15A C16A C11A 120.67(18) . . ? C15A C16A H16A 119.7 . . ? C11A C16A H16A 119.7 . . ? C11B C1B C2B 112.97(15) . . ? C11B C1B C6B 112.10(15) . . ? C2B C1B C6B 107.58(15) . . ? C11B C1B C7B 114.44(15) . . ? C2B C1B C7B 105.87(14) . . ? C6B C1B C7B 103.15(14) . . ? O2B C2B N3B 124.66(17) . . ? O2B C2B C1B 124.35(17) . . ? N3B C2B C1B 110.96(16) . . ? C2B N3B C4B 117.88(15) . . ? C2B N3B H3B 121.1 . . ? C4B N3B H3B 121.1 . . ? N3B C4B N5B 106.53(14) . . ? N3B C4B C9B 111.42(15) . . ? N5B C4B C9B 110.23(15) . . ? N3B C4B C8B 106.33(15) . . ? N5B C4B C8B 106.65(14) . . ? C9B C4B C8B 115.19(15) . . ? C6B N5B C4B 117.28(16) . . ? C6B N5B H5B 121.4 . . ? C4B N5B H5B 121.4 . . ? O6B C6B N5B 125.33(18) . . ? O6B C6B C1B 123.55(17) . . ? N5B C6B C1B 110.98(16) . . ? C8B C7B C1B 110.89(15) . . ? C8B C7B H7B1 109.5 . . ? C1B C7B H7B1 109.5 . . ? C8B C7B H7B2 109.5 . . ? C1B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 108.0 . . ? C4B C8B C7B 108.07(14) . . ? C4B C8B H8B1 110.1 . . ? C7B C8B H8B1 110.1 . . ? C4B C8B H8B2 110.1 . . ? C7B C8B H8B2 110.1 . . ? H8B1 C8B H8B2 108.4 . . ? C4B C9B C10B 113.72(16) . . ? C4B C9B H9B1 108.8 . . ? C10B C9B H9B1 108.8 . . ? C4B C9B H9B2 108.8 . . ? C10B C9B H9B2 108.8 . . ? H9B1 C9B H9B2 107.7 . . ? C9B C10B H10D 109.5 . . ? C9B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C9B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C12B C11B C16B 118.25(17) . . ? C12B C11B C1B 122.43(16) . . ? C16B C11B C1B 119.32(16) . . ? C13B C12B C11B 120.75(17) . . ? C13B C12B H12B 119.6 . . ? C11B C12B H12B 119.6 . . ? C14B C13B C12B 120.08(18) . . ? C14B C13B H13B 120.0 . . ? C12B C13B H13B 120.0 . . ? C13B C14B C15B 119.75(18) . . ? C13B C14B H14B 120.1 . . ? C15B C14B H14B 120.1 . . ? C16B C15B C14B 120.51(18) . . ? C16B C15B H15B 119.7 . . ? C14B C15B H15B 119.7 . . ? C15B C16B C11B 120.66(18) . . ? C15B C16B H16B 119.7 . . ? C11B C16B H16B 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11A C1A C2A O2A -7.6(3) . . . . ? C6A C1A C2A O2A -130.88(18) . . . . ? C7A C1A C2A O2A 118.48(19) . . . . ? C11A C1A C2A N3A 174.44(15) . . . . ? C6A C1A C2A N3A 51.15(19) . . . . ? C7A C1A C2A N3A -59.49(18) . . . . ? O2A C2A N3A C4A -175.64(17) . . . . ? C1A C2A N3A C4A 2.3(2) . . . . ? C2A N3A C4A N5A -54.5(2) . . . . ? C2A N3A C4A C9A -176.70(16) . . . . ? C2A N3A C4A C8A 59.4(2) . . . . ? N3A C4A N5A C6A 51.7(2) . . . . ? C9A C4A N5A C6A 173.49(16) . . . . ? C8A C4A N5A C6A -61.8(2) . . . . ? C4A N5A C6A O6A 179.91(17) . . . . ? C4A N5A C6A C1A 1.7(2) . . . . ? C11A C1A C6A O6A 3.5(3) . . . . ? C2A C1A C6A O6A 128.13(19) . . . . ? C7A C1A C6A O6A -120.59(19) . . . . ? C11A C1A C6A N5A -178.26(15) . . . . ? C2A C1A C6A N5A -53.67(19) . . . . ? C7A C1A C6A N5A 57.61(19) . . . . ? C11A C1A C7A C8A 179.99(15) . . . . ? C6A C1A C7A C8A -57.82(19) . . . . ? C2A C1A C7A C8A 54.46(19) . . . . ? N5A C4A C8A C7A 55.33(19) . . . . ? N3A C4A C8A C7A -58.38(19) . . . . ? C9A C4A C8A C7A 179.11(15) . . . . ? C1A C7A C8A C4A 2.8(2) . . . . ? N5A C4A C9A C10A -48.6(2) . . . . ? N3A C4A C9A C10A 70.6(2) . . . . ? C8A C4A C9A C10A -169.58(15) . . . . ? C6A C1A C11A C12A -110.32(19) . . . . ? C2A C1A C11A C12A 129.03(18) . . . . ? C7A C1A C11A C12A 7.9(3) . . . . ? C6A C1A C11A C16A 67.9(2) . . . . ? C2A C1A C11A C16A -52.8(2) . . . . ? C7A C1A C11A C16A -173.85(16) . . . . ? C16A C11A C12A C13A -1.3(3) . . . . ? C1A C11A C12A C13A 176.98(17) . . . . ? C11A C12A C13A C14A 1.1(3) . . . . ? C12A C13A C14A C15A -0.1(3) . . . . ? C13A C14A C15A C16A -0.6(3) . . . . ? C14A C15A C16A C11A 0.4(3) . . . . ? C12A C11A C16A C15A 0.5(3) . . . . ? C1A C11A C16A C15A -177.76(17) . . . . ? C11B C1B C2B O2B -5.2(2) . . . . ? C6B C1B C2B O2B -129.49(18) . . . . ? C7B C1B C2B O2B 120.75(19) . . . . ? C11B C1B C2B N3B 176.71(15) . . . . ? C6B C1B C2B N3B 52.46(19) . . . . ? C7B C1B C2B N3B -57.30(18) . . . . ? O2B C2B N3B C4B -178.38(16) . . . . ? C1B C2B N3B C4B -0.3(2) . . . . ? C2B N3B C4B N5B -52.4(2) . . . . ? C2B N3B C4B C9B -172.70(15) . . . . ? C2B N3B C4B C8B 61.04(19) . . . . ? N3B C4B N5B C6B 53.9(2) . . . . ? C9B C4B N5B C6B 174.96(15) . . . . ? C8B C4B N5B C6B -59.3(2) . . . . ? C4B N5B C6B O6B 173.55(16) . . . . ? C4B N5B C6B C1B -2.4(2) . . . . ? C11B C1B C6B O6B 8.4(2) . . . . ? C2B C1B C6B O6B 133.19(18) . . . . ? C7B C1B C6B O6B -115.18(18) . . . . ? C11B C1B C6B N5B -175.59(14) . . . . ? C2B C1B C6B N5B -50.81(19) . . . . ? C7B C1B C6B N5B 60.82(18) . . . . ? C11B C1B C7B C8B 179.21(15) . . . . ? C2B C1B C7B C8B 54.13(19) . . . . ? C6B C1B C7B C8B -58.75(19) . . . . ? N3B C4B C8B C7B -57.90(18) . . . . ? N5B C4B C8B C7B 55.50(19) . . . . ? C9B C4B C8B C7B 178.15(15) . . . . ? C1B C7B C8B C4B 2.1(2) . . . . ? N3B C4B C9B C10B -73.3(2) . . . . ? N5B C4B C9B C10B 168.61(15) . . . . ? C8B C4B C9B C10B 47.9(2) . . . . ? C2B C1B C11B C12B 123.58(18) . . . . ? C6B C1B C11B C12B -114.68(19) . . . . ? C7B C1B C11B C12B 2.3(2) . . . . ? C2B C1B C11B C16B -57.1(2) . . . . ? C6B C1B C11B C16B 64.6(2) . . . . ? C7B C1B C11B C16B -178.34(16) . . . . ? C16B C11B C12B C13B -0.1(3) . . . . ? C1B C11B C12B C13B 179.25(17) . . . . ? C11B C12B C13B C14B 0.3(3) . . . . ? C12B C13B C14B C15B -0.1(3) . . . . ? C13B C14B C15B C16B -0.4(3) . . . . ? C14B C15B C16B C11B 0.6(3) . . . . ? C12B C11B C16B C15B -0.4(3) . . . . ? C1B C11B C16B C15B -179.74(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.280 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.061 #===END