data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 D2 N6 O6.50' _chemical_formula_weight 363.34 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' 'D' 'D' 0.0000 0.0000 '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 6.951(2) _cell_length_b 10.718(4) _cell_length_c 11.123(4) _cell_angle_alpha 102.48(2) _cell_angle_beta 98.378(17) _cell_angle_gamma 105.812(13) _cell_volume 759.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.5300 _exptl_crystal_size_mid 0.2400 _exptl_crystal_size_min 0.2300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8332 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6473 _diffrn_reflns_av_R_equivalents 0.0818 _diffrn_reflns_av_sigmaI/netI 0.1540 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3393 _reflns_number_gt 1808 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1445P)^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 3393 _refine_ls_number_parameters 243 _refine_ls_number_restraints 333 _refine_ls_R_factor_all 0.1057 _refine_ls_R_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.2663 _refine_ls_wR_factor_gt 0.2034 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.895 _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 1.0583(5) 0.8190(3) 0.7479(3) 0.0184(7) Uani 1 1 d U . . C2 C 0.9168(5) 0.9052(3) 0.7531(3) 0.0159(7) Uani 1 1 d U . . C3 C 0.9744(5) 1.0295(3) 0.8441(3) 0.0174(7) Uani 1 1 d U . . H3A H 1.1027(5) 1.0611(3) 0.9043(3) 0.021 Uiso 1 1 d RU . . C4 C 0.8404(5) 1.1050(3) 0.8444(3) 0.0179(7) Uani 1 1 d U . . N5 N 0.9004(5) 1.2356(3) 0.9399(3) 0.0243(7) Uani 1 1 d U . . C6 C 0.6550(5) 1.0653(3) 0.7613(4) 0.0189(8) Uani 1 1 d U . . H6A H 0.5658(5) 1.1197(3) 0.7638(4) 0.023 Uiso 1 1 d RU . . C7 C 0.6044(5) 0.9423(3) 0.6736(3) 0.0154(7) Uani 1 1 d U . . N6 N 0.4070(4) 0.8960(3) 0.5818(3) 0.0193(7) Uani 1 1 d U . . C9 C 0.7285(5) 0.8609(3) 0.6670(3) 0.0150(7) Uani 1 1 d U . . H9A H 0.6868(5) 0.7756(3) 0.6050(3) 0.018 Uiso 1 1 d RU . . C10 C 0.4183(5) 0.6075(3) 0.8174(3) 0.0218(8) Uani 1 1 d U . . H10A H 0.5207(5) 0.6771(3) 0.7992(3) 0.026 Uiso 1 1 d RU . . H10B H 0.3856(5) 0.6446(3) 0.8954(3) 0.026 Uiso 1 1 d RU . . C11 C 0.3390(5) 0.3905(3) 0.8560(4) 0.0199(8) Uani 1 1 d U . . H11A H 0.3053(5) 0.4269(3) 0.9340(4) 0.024 Uiso 1 1 d RU . . H11B H 0.3926(5) 0.3189(3) 0.8664(4) 0.024 Uiso 1 1 d RU . . C12 C 0.0703(5) 0.4451(3) 0.7425(4) 0.0203(8) Uani 1 1 d U . . H12A H 0.0328(5) 0.4807(3) 0.8193(4) 0.024 Uiso 1 1 d RU . . H12B H -0.0506(5) 0.4108(3) 0.6759(4) 0.024 Uiso 1 1 d RU . . C13 C 0.2821(5) 0.4970(3) 0.5916(3) 0.0185(8) Uani 1 1 d U . . H13A H 0.3834(5) 0.5654(3) 0.5713(3) 0.022 Uiso 1 1 d RU . . H13B H 0.1626(5) 0.4640(3) 0.5241(3) 0.022 Uiso 1 1 d RU . . C14 C 0.5428(5) 0.4407(4) 0.7092(4) 0.0206(8) Uani 1 1 d U . . H14A H 0.5982(5) 0.3693(4) 0.7175(4) 0.025 Uiso 1 1 d RU . . H14B H 0.6455(5) 0.5093(4) 0.6901(4) 0.025 Uiso 1 1 d RU . . C15 C 0.2048(5) 0.2838(3) 0.6368(4) 0.0205(8) Uani 1 1 d U . . H15A H 0.0837(5) 0.2503(3) 0.5705(4) 0.025 Uiso 1 1 d RU . . H15B H 0.2553(5) 0.2100(3) 0.6430(4) 0.025 Uiso 1 1 d RU . . N1 N 0.4963(4) 0.4969(3) 0.8290(3) 0.0201(7) Uani 1 1 d U . . N2 N 0.1507(4) 0.3363(3) 0.7558(3) 0.0174(7) Uani 1 1 d U . . N3 N 0.2279(4) 0.5555(3) 0.7128(3) 0.0186(7) Uani 1 1 d U . . D3 D 0.1812 0.6244 0.7068 0.022 Uiso 1 1 d R . . N4 N 0.3614(4) 0.3878(3) 0.6044(3) 0.0168(6) Uani 1 1 d U . . O1 O 0.9851(4) 0.7030(2) 0.6722(3) 0.0245(7) Uani 1 1 d U . . O2 O 1.2344(4) 0.8677(3) 0.8162(3) 0.0297(7) Uani 1 1 d U . . O3 O 1.0512(4) 1.2645(3) 1.0240(3) 0.0332(7) Uani 1 1 d U . . O4 O 0.7959(4) 1.3104(3) 0.9282(3) 0.0361(8) Uani 1 1 d U . . O5 O 0.3132(4) 0.9769(3) 0.5747(3) 0.0283(7) Uani 1 1 d U . . O6 O 0.3474(4) 0.7793(2) 0.5154(3) 0.0308(7) Uani 1 1 d U . . OW O 1.5562(8) 0.8932(5) 1.0056(5) 0.0303(13) Uani 0.50 1 d PDU . . D1 D 1.458(10) 0.881(7) 0.938(5) 0.04(3) Uiso 0.50 1 d PD . . D2 D 1.613(9) 0.976(3) 1.059(5) 0.02(2) Uiso 0.50 1 d PD . . 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 0.0146(16) 0.0175(16) 0.0238(19) 0.0052(14) 0.0034(14) 0.0069(13) C2 0.0122(15) 0.0147(15) 0.0218(18) 0.0058(13) 0.0036(14) 0.0050(13) C3 0.0129(16) 0.0150(16) 0.0209(18) 0.0037(13) 0.0017(14) 0.0011(12) C4 0.0202(17) 0.0084(14) 0.0225(18) 0.0005(13) 0.0072(15) 0.0016(13) N5 0.0272(17) 0.0138(14) 0.0265(18) -0.0005(13) 0.0084(14) 0.0011(12) C6 0.0190(17) 0.0109(15) 0.030(2) 0.0046(14) 0.0112(15) 0.0074(13) C7 0.0098(15) 0.0115(15) 0.0237(19) 0.0050(13) 0.0024(14) 0.0023(12) N6 0.0107(14) 0.0181(14) 0.0307(18) 0.0075(13) 0.0029(12) 0.0072(11) C9 0.0134(15) 0.0101(14) 0.0209(18) 0.0034(13) 0.0028(13) 0.0036(12) C10 0.0214(18) 0.0136(16) 0.0233(19) -0.0013(14) 0.0039(15) -0.0005(13) C11 0.0154(17) 0.0196(17) 0.0212(18) 0.0058(14) -0.0011(14) 0.0024(13) C12 0.0125(16) 0.0223(17) 0.028(2) 0.0063(15) 0.0058(14) 0.0079(13) C13 0.0200(17) 0.0169(16) 0.0214(18) 0.0036(14) 0.0037(14) 0.0120(14) C14 0.0069(15) 0.0243(18) 0.030(2) 0.0064(15) 0.0015(14) 0.0066(13) C15 0.0177(17) 0.0129(15) 0.0261(19) 0.0003(14) -0.0003(15) 0.0037(13) N1 0.0103(13) 0.0212(14) 0.0232(16) 0.0030(12) -0.0012(12) 0.0011(11) N2 0.0112(13) 0.0132(13) 0.0246(16) 0.0026(12) -0.0005(12) 0.0027(11) N3 0.0186(15) 0.0119(13) 0.0263(17) 0.0027(12) 0.0057(13) 0.0080(11) N4 0.0136(14) 0.0144(13) 0.0221(16) 0.0027(11) 0.0015(12) 0.0068(11) O1 0.0230(14) 0.0176(13) 0.0323(16) 0.0005(11) 0.0004(12) 0.0132(11) O2 0.0114(12) 0.0304(15) 0.0444(18) 0.0060(13) -0.0014(12) 0.0088(11) O3 0.0388(17) 0.0223(14) 0.0263(16) -0.0003(12) 0.0021(13) -0.0022(12) O4 0.0412(17) 0.0168(13) 0.049(2) -0.0032(13) 0.0122(15) 0.0146(13) O5 0.0234(14) 0.0271(14) 0.0409(18) 0.0128(13) 0.0024(13) 0.0179(12) O6 0.0171(13) 0.0195(13) 0.0438(18) -0.0053(12) -0.0078(12) 0.0049(11) OW 0.027(3) 0.021(3) 0.030(3) -0.004(2) -0.008(2) 0.002(2) _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 O2 1.248(4) . ? C1 O1 1.261(4) . ? C1 C2 1.521(4) . ? C2 C9 1.398(5) . ? C2 C3 1.403(5) . ? C3 H3A 0.9602 . ? C3 C4 1.390(4) . ? C4 C6 1.371(5) . ? C4 N5 1.474(4) . ? N5 O3 1.217(4) . ? N5 O4 1.234(4) . ? C6 H6A 0.9600 . ? C6 C7 1.380(5) . ? C7 C9 1.382(4) . ? C7 N6 1.474(4) . ? N6 O5 1.227(3) . ? N6 O6 1.229(4) . ? C9 H9A 0.9600 . ? C10 H10B 0.9598 . ? C10 H10A 0.9601 . ? C10 N1 1.453(4) . ? C10 N3 1.511(4) . ? C11 H11B 0.9600 . ? C11 H11A 0.9600 . ? C11 N1 1.467(5) . ? C11 N2 1.475(4) . ? C12 H12B 0.9600 . ? C12 H12A 0.9600 . ? C12 N2 1.449(4) . ? C12 N3 1.509(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9601 . ? C13 N4 1.448(4) . ? C13 N3 1.504(4) . ? C14 H14B 0.9598 . ? C14 H14A 0.9602 . ? C14 N1 1.459(5) . ? C14 N4 1.472(4) . ? C15 H15B 0.9599 . ? C15 H15A 0.9599 . ? C15 N2 1.465(5) . ? C15 N4 1.478(5) . ? N3 D3 0.8952 . ? OW D1 0.896(19) . ? OW D2 0.901(19) . ? 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 O2 C1 O1 125.8(3) . . ? O2 C1 C2 118.5(3) . . ? O1 C1 C2 115.8(3) . . ? C9 C2 C3 119.6(3) . . ? C9 C2 C1 120.1(3) . . ? C3 C2 C1 120.3(3) . . ? H3A C3 C4 121.2(2) . . ? H3A C3 C2 120.69(18) . . ? C4 C3 C2 118.1(3) . . ? C6 C4 C3 124.0(3) . . ? C6 C4 N5 117.8(3) . . ? C3 C4 N5 118.2(3) . . ? O3 N5 O4 123.8(3) . . ? O3 N5 C4 118.5(3) . . ? O4 N5 C4 117.6(3) . . ? H6A C6 C4 122.04(18) . . ? H6A C6 C7 121.96(18) . . ? C4 C6 C7 116.0(3) . . ? C6 C7 C9 123.7(3) . . ? C6 C7 N6 117.8(3) . . ? C9 C7 N6 118.5(3) . . ? O5 N6 O6 123.8(3) . . ? O5 N6 C7 118.1(3) . . ? O6 N6 C7 118.2(2) . . ? H9A C9 C7 121.0(2) . . ? H9A C9 C2 120.37(18) . . ? C7 C9 C2 118.6(3) . . ? H10B C10 H10A 108.4 . . ? H10B C10 N1 109.6(2) . . ? H10A C10 N1 109.90(19) . . ? H10B C10 N3 109.70(18) . . ? H10A C10 N3 110.18(19) . . ? N1 C10 N3 109.1(3) . . ? H11B C11 H11A 108.0 . . ? H11B C11 N1 109.51(17) . . ? H11A C11 N1 108.67(19) . . ? H11B C11 N2 109.51(16) . . ? H11A C11 N2 108.74(19) . . ? N1 C11 N2 112.3(3) . . ? H12B C12 H12A 108.2 . . ? H12B C12 N2 109.21(18) . . ? H12A C12 N2 109.6(2) . . ? H12B C12 N3 109.74(18) . . ? H12A C12 N3 109.65(18) . . ? N2 C12 N3 110.5(3) . . ? H13A C13 H13B 108.3 . . ? H13A C13 N4 109.50(19) . . ? H13B C13 N4 109.49(18) . . ? H13A C13 N3 109.79(18) . . ? H13B C13 N3 109.78(17) . . ? N4 C13 N3 109.9(3) . . ? H14B C14 H14A 107.9 . . ? H14B C14 N1 108.98(19) . . ? H14A C14 N1 108.99(18) . . ? H14B C14 N4 109.22(19) . . ? H14A C14 N4 109.03(16) . . ? N1 C14 N4 112.6(3) . . ? H15B C15 H15A 108.0 . . ? H15B C15 N2 109.37(17) . . ? H15A C15 N2 108.92(17) . . ? H15B C15 N4 109.19(16) . . ? H15A C15 N4 109.15(18) . . ? N2 C15 N4 112.2(3) . . ? C10 N1 C14 108.8(3) . . ? C10 N1 C11 109.7(3) . . ? C14 N1 C11 108.0(3) . . ? C12 N2 C15 108.1(3) . . ? C12 N2 C11 108.8(3) . . ? C15 N2 C11 108.3(3) . . ? C13 N3 C12 108.4(3) . . ? C13 N3 C10 108.9(3) . . ? C12 N3 C10 109.2(3) . . ? C13 N3 D3 110.9 . . ? C12 N3 D3 111.2 . . ? C10 N3 D3 108.2 . . ? C13 N4 C14 108.4(3) . . ? C13 N4 C15 108.9(3) . . ? C14 N4 C15 108.2(3) . . ? D1 OW D2 119(3) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.857 _refine_diff_density_min -0.916 _refine_diff_density_rms 0.244