data_wue4935 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H12 N4' _chemical_formula_weight 272.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21/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 14.52870(10) _cell_length_b 5.13100(10) _cell_length_c 18.09840(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.7350(10) _cell_angle_gamma 90.00 _cell_volume 1292.03(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2190 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.690 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8465 _exptl_absorpt_correction_T_max 0.9533 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8735 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 67.68 _reflns_number_total 2213 _reflns_number_gt 1744 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _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 (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The hydrogens at N1 and N2 atoms were refined freely. ; _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^)+(0.0570P)^2^+0.3782P] 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 2213 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 N1 N 0.32446(10) 0.5027(3) 0.24390(8) 0.0383(4) Uani 1 1 d . . . H1A H 0.3626(15) 0.387(4) 0.2785(12) 0.059(6) Uiso 1 1 d . . . N2 N 0.45495(11) 0.6667(3) 0.20693(10) 0.0511(4) Uani 1 1 d . . . H2A H 0.4861(14) 0.523(4) 0.2426(12) 0.062(6) Uiso 1 1 d . . . N3 N 0.19471(10) 0.3246(3) 0.28228(8) 0.0392(4) Uani 1 1 d . . . N4 N 0.34752(10) 0.1370(3) 0.34821(8) 0.0481(4) Uani 1 1 d . . . C1 C 0.22963(11) 0.4899(3) 0.24265(9) 0.0354(4) Uani 1 1 d . . . C2 C 0.36523(12) 0.6716(3) 0.20251(9) 0.0386(4) Uani 1 1 d . . . C3 C 0.30058(12) 0.8611(3) 0.15233(9) 0.0377(4) Uani 1 1 d . . . C4 C 0.33504(13) 1.0386(3) 0.10988(10) 0.0440(4) Uani 1 1 d . . . H4 H 0.4007 1.0384 0.1128 0.053 Uiso 1 1 calc R . . C5 C 0.27345(14) 1.2194(4) 0.06236(10) 0.0489(5) Uani 1 1 d . . . H5 H 0.2979 1.3388 0.0334 0.059 Uiso 1 1 calc R . . C6 C 0.17799(14) 1.2233(3) 0.05787(10) 0.0477(5) Uani 1 1 d . . . H6 H 0.1374 1.3457 0.0257 0.057 Uiso 1 1 calc R . . C7 C 0.13930(13) 1.0464(3) 0.10076(9) 0.0408(4) Uani 1 1 d . . . C8 C 0.04149(13) 1.0496(4) 0.09966(10) 0.0473(5) Uani 1 1 d . . . H8 H -0.0004 1.1721 0.0686 0.057 Uiso 1 1 calc R . . C9 C 0.00707(13) 0.8782(4) 0.14282(10) 0.0493(5) Uani 1 1 d . . . H9 H -0.0580 0.8849 0.1417 0.059 Uiso 1 1 calc R . . C10 C 0.06812(12) 0.6917(4) 0.18886(10) 0.0435(4) Uani 1 1 d . . . H10 H 0.0431 0.5726 0.2175 0.052 Uiso 1 1 calc R . . C11 C 0.16422(11) 0.6803(3) 0.19269(9) 0.0361(4) Uani 1 1 d . . . C12 C 0.20143(11) 0.8610(3) 0.14881(9) 0.0356(4) Uani 1 1 d . . . C13 C 0.25124(12) 0.1418(3) 0.33252(9) 0.0384(4) Uani 1 1 d . . . C14 C 0.39695(14) -0.0431(4) 0.39748(11) 0.0543(5) Uani 1 1 d . . . H14 H 0.4642 -0.0452 0.4083 0.065 Uiso 1 1 calc R . . C15 C 0.35484(16) -0.2243(4) 0.43301(11) 0.0543(5) Uani 1 1 d . . . H15 H 0.3922 -0.3469 0.4675 0.065 Uiso 1 1 calc R . . C16 C 0.25580(15) -0.2217(4) 0.41666(10) 0.0511(5) Uani 1 1 d . . . H16 H 0.2245 -0.3440 0.4397 0.061 Uiso 1 1 calc R . . C17 C 0.20386(13) -0.0392(3) 0.36662(9) 0.0455(4) Uani 1 1 d . . . H17 H 0.1365 -0.0353 0.3552 0.055 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 N1 0.0384(8) 0.0376(8) 0.0384(8) 0.0022(6) 0.0105(6) 0.0022(6) N2 0.0408(9) 0.0479(9) 0.0655(10) 0.0049(8) 0.0167(7) 0.0005(7) N3 0.0444(8) 0.0352(8) 0.0374(7) 0.0008(6) 0.0109(6) -0.0009(6) N4 0.0472(9) 0.0488(9) 0.0478(8) 0.0081(7) 0.0127(7) 0.0061(7) C1 0.0389(9) 0.0332(9) 0.0337(8) -0.0061(7) 0.0100(7) -0.0007(7) C2 0.0407(9) 0.0346(9) 0.0412(9) -0.0044(7) 0.0131(7) -0.0042(7) C3 0.0438(9) 0.0341(9) 0.0348(8) -0.0052(7) 0.0110(7) -0.0024(7) C4 0.0493(10) 0.0416(10) 0.0420(9) -0.0028(8) 0.0149(8) -0.0068(8) C5 0.0654(12) 0.0409(10) 0.0410(10) 0.0018(8) 0.0161(9) -0.0081(9) C6 0.0653(12) 0.0384(10) 0.0354(9) 0.0017(7) 0.0080(8) 0.0021(9) C7 0.0498(10) 0.0370(9) 0.0325(8) -0.0032(7) 0.0069(7) 0.0016(8) C8 0.0494(10) 0.0448(10) 0.0419(9) 0.0002(8) 0.0038(8) 0.0085(8) C9 0.0400(10) 0.0555(12) 0.0500(10) -0.0013(9) 0.0093(8) 0.0054(8) C10 0.0415(9) 0.0469(10) 0.0417(9) 0.0006(8) 0.0112(7) -0.0007(8) C11 0.0404(9) 0.0337(9) 0.0323(8) -0.0039(7) 0.0077(7) 0.0004(7) C12 0.0431(9) 0.0328(9) 0.0304(8) -0.0060(6) 0.0096(7) -0.0014(7) C13 0.0462(10) 0.0347(9) 0.0340(8) -0.0026(7) 0.0111(7) 0.0012(7) C14 0.0546(11) 0.0541(12) 0.0519(11) 0.0100(9) 0.0118(9) 0.0137(9) C15 0.0745(14) 0.0431(11) 0.0427(10) 0.0062(8) 0.0126(9) 0.0119(10) C16 0.0709(13) 0.0398(10) 0.0423(10) 0.0022(8) 0.0159(9) -0.0052(9) C17 0.0543(11) 0.0420(10) 0.0393(9) -0.0004(8) 0.0121(8) -0.0051(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 N1 C1 1.373(2) . ? N1 C2 1.385(2) . ? N1 H1A 0.92(2) . ? N2 C2 1.283(2) . ? N2 H2A 1.00(2) . ? N3 C1 1.304(2) . ? N3 C13 1.397(2) . ? N4 C14 1.340(2) . ? N4 C13 1.345(2) . ? C1 C11 1.477(2) . ? C2 C3 1.470(2) . ? C3 C4 1.375(2) . ? C3 C12 1.423(2) . ? C4 C5 1.399(3) . ? C4 H4 0.9400 . ? C5 C6 1.366(3) . ? C5 H5 0.9400 . ? C6 C7 1.412(3) . ? C6 H6 0.9400 . ? C7 C8 1.416(2) . ? C7 C12 1.423(2) . ? C8 C9 1.364(3) . ? C8 H8 0.9400 . ? C9 C10 1.404(2) . ? C9 H9 0.9400 . ? C10 C11 1.379(2) . ? C10 H10 0.9400 . ? C11 C12 1.425(2) . ? C13 C17 1.401(2) . ? C14 C15 1.371(3) . ? C14 H14 0.9400 . ? C15 C16 1.383(3) . ? C15 H15 0.9400 . ? C16 C17 1.369(3) . ? C16 H16 0.9400 . ? C17 H17 0.9400 . ? 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 C2 127.19(15) . . ? C1 N1 H1A 112.6(12) . . ? C2 N1 H1A 120.2(13) . . ? C2 N2 H2A 108.5(12) . . ? C1 N3 C13 123.09(14) . . ? C14 N4 C13 118.59(16) . . ? N3 C1 N1 124.71(15) . . ? N3 C1 C11 118.91(14) . . ? N1 C1 C11 116.38(14) . . ? N2 C2 N1 122.64(16) . . ? N2 C2 C3 120.54(15) . . ? N1 C2 C3 116.82(15) . . ? C4 C3 C12 120.11(15) . . ? C4 C3 C2 120.83(15) . . ? C12 C3 C2 119.06(14) . . ? C3 C4 C5 120.73(17) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 120.34(17) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 121.06(17) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C8 122.79(16) . . ? C6 C7 C12 118.88(16) . . ? C8 C7 C12 118.30(16) . . ? C9 C8 C7 121.10(16) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 120.44(17) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 121.06(16) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 119.06(15) . . ? C10 C11 C1 121.50(15) . . ? C12 C11 C1 119.43(14) . . ? C7 C12 C3 118.88(15) . . ? C7 C12 C11 120.01(15) . . ? C3 C12 C11 121.12(14) . . ? N4 C13 N3 122.03(15) . . ? N4 C13 C17 120.53(15) . . ? N3 C13 C17 117.43(15) . . ? N4 C14 C15 123.64(19) . . ? N4 C14 H14 118.2 . . ? C15 C14 H14 118.2 . . ? C14 C15 C16 118.05(17) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C17 C16 C15 119.33(18) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C13 119.86(17) . . ? C16 C17 H17 120.1 . . ? C13 C17 H17 120.1 . . ? 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 C13 N3 C1 N1 1.3(2) . . . . ? C13 N3 C1 C11 -178.35(13) . . . . ? C2 N1 C1 N3 179.21(15) . . . . ? C2 N1 C1 C11 -1.2(2) . . . . ? C1 N1 C2 N2 -179.22(15) . . . . ? C1 N1 C2 C3 0.9(2) . . . . ? N2 C2 C3 C4 -0.7(2) . . . . ? N1 C2 C3 C4 179.14(14) . . . . ? N2 C2 C3 C12 180.00(15) . . . . ? N1 C2 C3 C12 -0.1(2) . . . . ? C12 C3 C4 C5 -0.5(2) . . . . ? C2 C3 C4 C5 -179.77(15) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 C8 177.87(16) . . . . ? C5 C6 C7 C12 -0.4(2) . . . . ? C6 C7 C8 C9 -178.97(16) . . . . ? C12 C7 C8 C9 -0.7(2) . . . . ? C7 C8 C9 C10 -0.7(3) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? C9 C10 C11 C1 178.22(15) . . . . ? N3 C1 C11 C10 1.9(2) . . . . ? N1 C1 C11 C10 -177.75(14) . . . . ? N3 C1 C11 C12 -179.68(14) . . . . ? N1 C1 C11 C12 0.7(2) . . . . ? C6 C7 C12 C3 0.3(2) . . . . ? C8 C7 C12 C3 -178.03(14) . . . . ? C6 C7 C12 C11 180.00(14) . . . . ? C8 C7 C12 C11 1.6(2) . . . . ? C4 C3 C12 C7 0.1(2) . . . . ? C2 C3 C12 C7 179.39(14) . . . . ? C4 C3 C12 C11 -179.53(15) . . . . ? C2 C3 C12 C11 -0.3(2) . . . . ? C10 C11 C12 C7 -1.2(2) . . . . ? C1 C11 C12 C7 -179.67(13) . . . . ? C10 C11 C12 C3 178.45(14) . . . . ? C1 C11 C12 C3 0.0(2) . . . . ? C14 N4 C13 N3 179.50(16) . . . . ? C14 N4 C13 C17 -0.5(2) . . . . ? C1 N3 C13 N4 5.4(2) . . . . ? C1 N3 C13 C17 -174.66(15) . . . . ? C13 N4 C14 C15 0.1(3) . . . . ? N4 C14 C15 C16 0.4(3) . . . . ? C14 C15 C16 C17 -0.5(3) . . . . ? C15 C16 C17 C13 0.1(3) . . . . ? N4 C13 C17 C16 0.4(2) . . . . ? N3 C13 C17 C16 -179.61(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N4 0.92(2) 1.86(2) 2.614(2) 137.8(17) . N2 H2A N2 1.00(2) 2.11(2) 3.0903(19) 166.2(17) 2_645 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 67.68 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.148 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.035