data_mha92_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H15 N3 O2 S' _chemical_formula_weight 253.32 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 14.3413(7) _cell_length_b 6.0078(3) _cell_length_c 16.2414(7) _cell_angle_alpha 90.00 _cell_angle_beta 117.557(3) _cell_angle_gamma 90.00 _cell_volume 1240.60(10) _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 0.65 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8521 _exptl_absorpt_correction_T_max 0.9799 _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 12899 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 28.99 _reflns_number_total 3287 _reflns_number_gt 2224 _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^)+(0.0323P)^2^+0.6060P] 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 3287 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.13715(4) 1.20743(8) 0.92648(4) 0.02385(15) Uani 1 1 d . . . O1 O 0.69829(10) 0.3708(2) 0.90702(9) 0.0195(3) Uani 1 1 d . . . O2 O 0.61501(11) 0.6992(2) 0.95666(9) 0.0185(3) Uani 1 1 d . . . N1 N 0.30387(12) 0.7420(2) 0.88592(11) 0.0172(4) Uani 1 1 d . . . N2 N 0.27398(13) 0.9356(3) 0.91250(12) 0.0183(4) Uani 1 1 d . . . N3 N 0.10983(13) 0.7903(3) 0.86142(13) 0.0233(4) Uani 1 1 d . . . C1 C 0.38028(15) 0.3565(3) 0.83118(13) 0.0176(4) Uani 1 1 d . . . H1A H 0.3075 0.3570 0.8146 0.021 Uiso 1 1 calc R . . C2 C 0.42204(15) 0.1824(3) 0.80421(13) 0.0188(4) Uani 1 1 d . . . H2A H 0.3774 0.0646 0.7685 0.023 Uiso 1 1 calc R . . C3 C 0.52951(15) 0.1756(3) 0.82860(13) 0.0175(4) Uani 1 1 d . . . H3A H 0.5580 0.0537 0.8104 0.021 Uiso 1 1 calc R . . C4 C 0.59310(14) 0.3487(3) 0.87944(13) 0.0160(4) Uani 1 1 d . . . C5 C 0.55096(14) 0.5285(3) 0.90682(12) 0.0155(4) Uani 1 1 d . . . C6 C 0.44456(14) 0.5345(3) 0.88326(13) 0.0151(4) Uani 1 1 d . . . C7 C 0.40250(14) 0.7253(3) 0.91044(13) 0.0158(4) Uani 1 1 d . . . H7A H 0.4489 0.8397 0.9470 0.019 Uiso 1 1 calc R . . C8 C 0.17326(15) 0.9633(3) 0.89746(13) 0.0178(4) Uani 1 1 d . . . C9 C 0.00005(16) 0.7866(4) 0.84092(17) 0.0320(5) Uani 1 1 d . . . H9A H -0.0289 0.6375 0.8198 0.048 Uiso 1 1 calc R . . H9B H -0.0393 0.8953 0.7921 0.048 Uiso 1 1 calc R . . H9C H -0.0058 0.8243 0.8971 0.048 Uiso 1 1 calc R . . C10 C 0.74644(15) 0.2198(3) 0.86907(14) 0.0220(4) Uani 1 1 d . . . H10A H 0.7010 0.2003 0.8015 0.026 Uiso 1 1 calc R . . H10B H 0.7576 0.0725 0.8995 0.026 Uiso 1 1 calc R . . C11 C 0.84951(17) 0.3208(4) 0.88700(18) 0.0401(6) Uani 1 1 d . . . H11A H 0.8860 0.2211 0.8637 0.060 Uiso 1 1 calc R . . H11B H 0.8929 0.3429 0.9539 0.060 Uiso 1 1 calc R . . H11C H 0.8371 0.4646 0.8551 0.060 Uiso 1 1 calc R . . H1N2 H 0.3185(17) 1.037(4) 0.9423(15) 0.027(6) Uiso 1 1 d . . . H1N3 H 0.1379(16) 0.675(4) 0.8550(14) 0.021(6) Uiso 1 1 d . . . H1O2 H 0.6765(19) 0.670(4) 0.9703(16) 0.036(7) 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 0.0201(3) 0.0171(3) 0.0342(3) -0.0021(2) 0.0125(2) 0.0033(2) O1 0.0187(7) 0.0199(7) 0.0227(7) -0.0034(6) 0.0120(6) 0.0022(6) O2 0.0152(7) 0.0160(7) 0.0238(8) -0.0043(6) 0.0086(6) -0.0009(6) N1 0.0215(8) 0.0132(8) 0.0195(8) -0.0008(7) 0.0116(7) 0.0013(6) N2 0.0180(9) 0.0120(8) 0.0248(9) -0.0048(7) 0.0097(8) -0.0011(7) N3 0.0175(9) 0.0175(9) 0.0359(11) -0.0044(8) 0.0131(8) -0.0009(7) C1 0.0193(10) 0.0173(10) 0.0185(10) 0.0010(8) 0.0106(8) -0.0020(8) C2 0.0253(10) 0.0136(10) 0.0195(10) -0.0030(8) 0.0120(9) -0.0059(8) C3 0.0260(10) 0.0133(10) 0.0176(10) 0.0005(8) 0.0137(9) 0.0018(8) C4 0.0185(10) 0.0162(10) 0.0158(10) 0.0032(8) 0.0099(8) 0.0026(8) C5 0.0195(10) 0.0138(9) 0.0141(9) -0.0004(8) 0.0084(8) -0.0025(7) C6 0.0201(10) 0.0129(9) 0.0141(9) 0.0020(8) 0.0096(8) 0.0003(7) C7 0.0177(9) 0.0139(9) 0.0163(9) 0.0011(8) 0.0082(8) -0.0006(7) C8 0.0171(10) 0.0176(10) 0.0178(10) 0.0021(8) 0.0072(8) 0.0002(8) C9 0.0184(11) 0.0282(12) 0.0481(14) -0.0060(11) 0.0142(10) -0.0053(9) C10 0.0260(10) 0.0194(10) 0.0254(11) 0.0002(9) 0.0160(9) 0.0063(8) C11 0.0297(13) 0.0461(15) 0.0520(16) -0.0132(13) 0.0252(12) 0.0006(11) _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 1.693(2) . ? O1 C4 1.367(2) . ? O1 C10 1.440(2) . ? O2 C5 1.365(2) . ? O2 H1O2 0.82(2) . ? N1 C7 1.284(2) . ? N1 N2 1.376(2) . ? N2 C8 1.359(2) . ? N2 H1N2 0.85(2) . ? N3 C8 1.326(2) . ? N3 C9 1.451(3) . ? N3 H1N3 0.83(2) . ? C1 C2 1.374(3) . ? C1 C6 1.410(3) . ? C1 H1A 0.9500 . ? C2 C3 1.403(3) . ? C2 H2A 0.9500 . ? C3 C4 1.378(3) . ? C3 H3A 0.9500 . ? C4 C5 1.406(3) . ? C5 C6 1.391(3) . ? C6 C7 1.455(3) . ? C7 H7A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.497(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 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 C4 O1 C10 118.25(15) . . ? C5 O2 H1O2 110.1(17) . . ? C7 N1 N2 115.29(16) . . ? C8 N2 N1 120.43(16) . . ? C8 N2 H1N2 118.1(14) . . ? N1 N2 H1N2 121.3(15) . . ? C8 N3 C9 124.30(18) . . ? C8 N3 H1N3 115.9(14) . . ? C9 N3 H1N3 119.6(14) . . ? C2 C1 C6 120.57(17) . . ? C2 C1 H1A 119.7 . . ? C6 C1 H1A 119.7 . . ? C1 C2 C3 121.04(18) . . ? C1 C2 H2A 119.5 . . ? C3 C2 H2A 119.5 . . ? C4 C3 C2 118.91(17) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? O1 C4 C3 126.44(17) . . ? O1 C4 C5 113.09(16) . . ? C3 C4 C5 120.46(17) . . ? O2 C5 C6 119.66(17) . . ? O2 C5 C4 119.66(16) . . ? C6 C5 C4 120.68(17) . . ? C5 C6 C1 118.33(17) . . ? C5 C6 C7 119.53(17) . . ? C1 C6 C7 122.11(17) . . ? N1 C7 C6 121.28(17) . . ? N1 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? N3 C8 N2 116.00(17) . . ? N3 C8 S1 124.49(15) . . ? N2 C8 S1 119.51(14) . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 C11 106.69(17) . . ? O1 C10 H10A 110.4 . . ? C11 C10 H10A 110.4 . . ? O1 C10 H10B 110.4 . . ? C11 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 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 C7 N1 N2 C8 -174.28(17) . . . . ? C6 C1 C2 C3 0.8(3) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? C10 O1 C4 C3 10.1(3) . . . . ? C10 O1 C4 C5 -168.78(16) . . . . ? C2 C3 C4 O1 -178.41(17) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? O1 C4 C5 O2 -0.7(2) . . . . ? C3 C4 C5 O2 -179.59(17) . . . . ? O1 C4 C5 C6 179.03(16) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? O2 C5 C6 C1 179.55(16) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? O2 C5 C6 C7 1.3(3) . . . . ? C4 C5 C6 C7 -178.43(16) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C2 C1 C6 C7 177.95(17) . . . . ? N2 N1 C7 C6 -177.00(16) . . . . ? C5 C6 C7 N1 176.44(18) . . . . ? C1 C6 C7 N1 -1.8(3) . . . . ? C9 N3 C8 N2 179.56(19) . . . . ? C9 N3 C8 S1 0.6(3) . . . . ? N1 N2 C8 N3 3.7(3) . . . . ? N1 N2 C8 S1 -177.32(13) . . . . ? C4 O1 C10 C11 163.28(18) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.363 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.072