data_mha94a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 N3 O2 S' _chemical_formula_weight 239.29 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 12.8547(5) _cell_length_b 5.9945(2) _cell_length_c 16.0739(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.494(2) _cell_angle_gamma 90.00 _cell_volume 1217.90(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8849 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 16551 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 30.16 _reflns_number_total 3589 _reflns_number_gt 2785 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0354P)^2^+0.7655P] 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 3589 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 S1 S 0.36343(3) -0.22295(6) -0.00616(3) 0.02027(11) Uani 1 1 d . . . O1 O -0.12034(9) 0.30491(18) 0.07215(7) 0.0165(2) Uani 1 1 d . . . O2 O -0.20679(8) 0.63869(18) 0.14177(7) 0.0179(2) Uani 1 1 d . . . N1 N 0.19417(10) 0.2548(2) 0.06980(8) 0.0148(3) Uani 1 1 d . . . N2 N 0.22473(10) 0.0599(2) 0.03544(9) 0.0160(3) Uani 1 1 d . . . N3 N 0.39421(12) 0.1904(2) 0.05677(10) 0.0234(3) Uani 1 1 d . . . C1 C -0.05659(12) 0.4764(2) 0.10624(9) 0.0132(3) Uani 1 1 d . . . C2 C -0.10033(12) 0.6576(2) 0.14385(9) 0.0142(3) Uani 1 1 d . . . C3 C -0.03582(13) 0.8310(2) 0.17931(10) 0.0162(3) Uani 1 1 d . . . H3A H -0.0648 0.9540 0.2046 0.019 Uiso 1 1 calc R . . C4 C 0.07297(13) 0.8226(2) 0.17746(10) 0.0165(3) Uani 1 1 d . . . H4A H 0.1176 0.9403 0.2022 0.020 Uiso 1 1 calc R . . C5 C 0.11586(12) 0.6461(2) 0.14030(9) 0.0147(3) Uani 1 1 d . . . H5A H 0.1895 0.6439 0.1390 0.018 Uiso 1 1 calc R . . C6 C 0.05108(12) 0.4689(2) 0.10421(9) 0.0128(3) Uani 1 1 d . . . C7 C 0.09410(12) 0.2757(2) 0.06678(9) 0.0140(3) Uani 1 1 d . . . H7A H 0.0475 0.1638 0.0398 0.017 Uiso 1 1 calc R . . C8 C 0.32712(12) 0.0256(3) 0.03095(10) 0.0161(3) Uani 1 1 d . . . C9 C -0.25612(13) 0.8014(3) 0.18838(11) 0.0214(3) Uani 1 1 d . . . H9A H -0.2544 0.9508 0.1624 0.026 Uiso 1 1 calc R . . H9B H -0.2182 0.8094 0.2477 0.026 Uiso 1 1 calc R . . C10 C -0.36884(14) 0.7279(4) 0.18540(13) 0.0346(5) Uani 1 1 d . . . H10A H -0.4051 0.8356 0.2161 0.052 Uiso 1 1 calc R . . H10B H -0.3695 0.5807 0.2118 0.052 Uiso 1 1 calc R . . H10C H -0.4053 0.7195 0.1264 0.052 Uiso 1 1 calc R . . H1N2 H 0.1776(16) -0.040(3) 0.0178(12) 0.027(5) Uiso 1 1 d . . . H1N3 H 0.4565(17) 0.182(3) 0.0460(12) 0.027(5) Uiso 1 1 d . . . H2N3 H 0.3682(17) 0.321(4) 0.0688(14) 0.038(6) Uiso 1 1 d . . . H1O1 H -0.1848(19) 0.337(4) 0.0712(14) 0.041(6) Uiso 1 1 d . . . 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 S1 0.01307(19) 0.01477(18) 0.0339(2) -0.00448(16) 0.00670(16) 0.00066(14) O1 0.0109(5) 0.0156(5) 0.0232(6) -0.0049(4) 0.0035(4) -0.0010(4) O2 0.0141(5) 0.0198(5) 0.0208(6) -0.0040(4) 0.0056(4) 0.0035(4) N1 0.0163(6) 0.0135(6) 0.0156(6) -0.0006(5) 0.0053(5) 0.0013(5) N2 0.0123(6) 0.0128(6) 0.0238(7) -0.0041(5) 0.0054(5) -0.0006(5) N3 0.0131(7) 0.0200(7) 0.0388(9) -0.0101(6) 0.0090(6) -0.0026(6) C1 0.0146(7) 0.0129(6) 0.0121(7) -0.0004(5) 0.0024(6) -0.0011(5) C2 0.0152(7) 0.0159(6) 0.0120(7) 0.0018(5) 0.0036(6) 0.0019(5) C3 0.0223(8) 0.0127(6) 0.0144(8) -0.0003(5) 0.0055(6) 0.0018(6) C4 0.0200(8) 0.0143(7) 0.0156(8) -0.0010(5) 0.0040(6) -0.0036(6) C5 0.0153(7) 0.0142(6) 0.0151(8) 0.0012(5) 0.0042(6) -0.0010(5) C6 0.0151(7) 0.0123(6) 0.0114(7) 0.0016(5) 0.0031(5) 0.0012(5) C7 0.0148(7) 0.0133(6) 0.0142(7) -0.0006(5) 0.0033(6) -0.0008(5) C8 0.0135(7) 0.0173(7) 0.0181(8) -0.0003(6) 0.0046(6) -0.0005(6) C9 0.0210(8) 0.0239(8) 0.0201(8) -0.0039(6) 0.0064(7) 0.0070(6) C10 0.0208(9) 0.0475(12) 0.0381(11) -0.0100(9) 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 S1 C8 1.7017(16) . ? O1 C1 1.3658(17) . ? O1 H1O1 0.85(2) . ? O2 C2 1.3675(18) . ? O2 C9 1.4450(18) . ? N1 C7 1.2845(19) . ? N1 N2 1.3795(17) . ? N2 C8 1.3470(19) . ? N2 H1N2 0.86(2) . ? N3 C8 1.327(2) . ? N3 H1N3 0.85(2) . ? N3 H2N3 0.89(2) . ? C1 C6 1.391(2) . ? C1 C2 1.409(2) . ? C2 C3 1.386(2) . ? C3 C4 1.405(2) . ? C3 H3A 0.9500 . ? C4 C5 1.379(2) . ? C4 H4A 0.9500 . ? C5 C6 1.408(2) . ? C5 H5A 0.9500 . ? C6 C7 1.460(2) . ? C7 H7A 0.9500 . ? C9 C10 1.507(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 C1 O1 H1O1 110.6(16) . . ? C2 O2 C9 117.59(12) . . ? C7 N1 N2 115.06(13) . . ? C8 N2 N1 120.20(13) . . ? C8 N2 H1N2 120.7(13) . . ? N1 N2 H1N2 119.1(13) . . ? C8 N3 H1N3 118.4(14) . . ? C8 N3 H2N3 118.5(14) . . ? H1N3 N3 H2N3 120.0(19) . . ? O1 C1 C6 119.52(13) . . ? O1 C1 C2 119.69(13) . . ? C6 C1 C2 120.78(13) . . ? O2 C2 C3 126.39(14) . . ? O2 C2 C1 113.67(13) . . ? C3 C2 C1 119.93(14) . . ? C2 C3 C4 119.19(14) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C5 C4 C3 120.98(14) . . ? C5 C4 H4A 119.5 . . ? C3 C4 H4A 119.5 . . ? C4 C5 C6 120.29(14) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C1 C6 C5 118.82(13) . . ? C1 C6 C7 119.27(13) . . ? C5 C6 C7 121.89(13) . . ? N1 C7 C6 120.92(13) . . ? N1 C7 H7A 119.5 . . ? C6 C7 H7A 119.5 . . ? N3 C8 N2 117.09(14) . . ? N3 C8 S1 123.86(12) . . ? N2 C8 S1 119.05(11) . . ? O2 C9 C10 107.23(14) . . ? O2 C9 H9A 110.3 . . ? C10 C9 H9A 110.3 . . ? O2 C9 H9B 110.3 . . ? C10 C9 H9B 110.3 . . ? H9A C9 H9B 108.5 . . ? 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 . . ? 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 C7 N1 N2 C8 176.36(14) . . . . ? C9 O2 C2 C3 -7.0(2) . . . . ? C9 O2 C2 C1 172.11(13) . . . . ? O1 C1 C2 O2 0.15(19) . . . . ? C6 C1 C2 O2 -179.14(13) . . . . ? O1 C1 C2 C3 179.34(13) . . . . ? C6 C1 C2 C3 0.1(2) . . . . ? O2 C2 C3 C4 178.79(14) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 -0.7(2) . . . . ? O1 C1 C6 C5 -179.43(13) . . . . ? C2 C1 C6 C5 -0.1(2) . . . . ? O1 C1 C6 C7 -1.0(2) . . . . ? C2 C1 C6 C7 178.34(13) . . . . ? C4 C5 C6 C1 0.5(2) . . . . ? C4 C5 C6 C7 -177.96(14) . . . . ? N2 N1 C7 C6 177.22(13) . . . . ? C1 C6 C7 N1 -174.45(14) . . . . ? C5 C6 C7 N1 4.0(2) . . . . ? N1 N2 C8 N3 -3.3(2) . . . . ? N1 N2 C8 S1 176.26(11) . . . . ? C2 O2 C9 C10 -172.87(14) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.16 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.341 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.066