data_mo_mha72_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N3 O S' _chemical_formula_weight 273.35 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' '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' _cell_length_a 9.2934(14) _cell_length_b 5.0115(8) _cell_length_c 14.736(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.620(3) _cell_angle_gamma 90.00 _cell_volume 667.03(18) _cell_formula_units_Z 2 _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 0.50 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8899 _exptl_absorpt_correction_T_max 0.9936 _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 7884 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3684 _reflns_number_gt 3196 _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^)+(0.0436P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.59(7) _refine_ls_number_reflns 3684 _refine_ls_number_parameters 185 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _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 0.70370(4) 1.06470(12) 0.56838(3) 0.01644(11) Uani 1 1 d . . . O1 O 0.56558(14) 0.3525(3) 0.87499(9) 0.0181(3) Uani 1 1 d . . . N1 N 0.52798(15) 0.5309(4) 0.70525(10) 0.0142(4) Uani 1 1 d . . . N2 N 0.55645(16) 0.6920(4) 0.63565(10) 0.0151(3) Uani 1 1 d . . . N3 N 0.73462(16) 0.9083(4) 0.74495(11) 0.0153(3) Uani 1 1 d . . . C1 C 0.45390(18) 0.1801(4) 0.84007(12) 0.0150(4) Uani 1 1 d . . . C2 C 0.41107(19) 0.0109(4) 0.90560(12) 0.0179(5) Uani 1 1 d . . . H2A H 0.4587 0.0244 0.9700 0.021 Uiso 1 1 calc R . . C3 C 0.30091(19) -0.1727(5) 0.87630(13) 0.0178(4) Uani 1 1 d . . . H3A H 0.2733 -0.2866 0.9209 0.021 Uiso 1 1 calc R . . C4 C 0.22704(18) -0.1964(4) 0.78070(12) 0.0147(4) Uani 1 1 d . . . C5 C 0.11366(18) -0.3895(4) 0.75014(13) 0.0175(5) Uani 1 1 d . . . H5A H 0.0869 -0.5046 0.7947 0.021 Uiso 1 1 calc R . . C6 C 0.04214(18) -0.4131(5) 0.65781(13) 0.0179(4) Uani 1 1 d . . . H6A H -0.0342 -0.5413 0.6385 0.022 Uiso 1 1 calc R . . C7 C 0.08402(18) -0.2434(4) 0.59196(13) 0.0169(4) Uani 1 1 d . . . H7A H 0.0354 -0.2593 0.5278 0.020 Uiso 1 1 calc R . . C8 C 0.19340(18) -0.0562(4) 0.61860(13) 0.0149(4) Uani 1 1 d . . . H8A H 0.2193 0.0544 0.5725 0.018 Uiso 1 1 calc R . . C9 C 0.26877(18) -0.0244(4) 0.71364(12) 0.0123(4) Uani 1 1 d . . . C10 C 0.38454(18) 0.1680(4) 0.74469(12) 0.0128(4) Uani 1 1 d . . . C11 C 0.42650(18) 0.3510(4) 0.67893(12) 0.0142(4) Uani 1 1 d . . . H11A H 0.3781 0.3384 0.6147 0.017 Uiso 1 1 calc R . . C12 C 0.66427(18) 0.8803(4) 0.65507(12) 0.0139(4) Uani 1 1 d . . . C13 C 0.85344(17) 1.1005(5) 0.77948(12) 0.0163(4) Uani 1 1 d . . . H13A H 0.8152 1.2846 0.7670 0.020 Uiso 1 1 calc R . . H13B H 0.9342 1.0743 0.7470 0.020 Uiso 1 1 calc R . . C14 C 0.91196(19) 1.0596(7) 0.88385(12) 0.0250(4) Uani 1 1 d . . . H14A H 0.9914 1.1880 0.9076 0.038 Uiso 1 1 calc R . . H14B H 0.9506 0.8777 0.8956 0.038 Uiso 1 1 calc R . . H14C H 0.8316 1.0866 0.9156 0.038 Uiso 1 1 calc R . . H1N3 H 0.705(2) 0.801(6) 0.7871(18) 0.031(7) Uiso 1 1 d . . . H1N2 H 0.513(3) 0.658(6) 0.5728(18) 0.044(8) Uiso 1 1 d . . . H1O1 H 0.576(3) 0.447(6) 0.830(2) 0.043(8) 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 0.01697(19) 0.0186(2) 0.01356(18) 0.0016(2) 0.00333(13) -0.0035(2) O1 0.0203(6) 0.0200(8) 0.0133(6) -0.0005(6) 0.0025(5) -0.0062(6) N1 0.0146(6) 0.0153(10) 0.0133(6) 0.0019(7) 0.0047(5) 0.0003(7) N2 0.0172(7) 0.0159(9) 0.0116(7) 0.0000(7) 0.0022(5) -0.0049(7) N3 0.0150(7) 0.0161(10) 0.0144(7) 0.0001(7) 0.0025(6) -0.0042(7) C1 0.0138(8) 0.0160(10) 0.0153(8) -0.0016(8) 0.0034(6) -0.0011(7) C2 0.0204(8) 0.0206(14) 0.0126(7) 0.0005(8) 0.0036(6) 0.0003(8) C3 0.0216(8) 0.0167(11) 0.0160(8) 0.0021(8) 0.0065(7) -0.0022(8) C4 0.0140(7) 0.0136(11) 0.0171(8) 0.0002(8) 0.0052(6) 0.0011(7) C5 0.0155(8) 0.0165(13) 0.0218(8) 0.0018(8) 0.0070(6) 0.0000(8) C6 0.0146(7) 0.0161(11) 0.0230(8) -0.0030(10) 0.0041(6) -0.0013(9) C7 0.0148(8) 0.0159(11) 0.0182(8) -0.0006(8) 0.0003(6) 0.0008(8) C8 0.0147(8) 0.0141(10) 0.0149(8) 0.0011(8) 0.0018(6) 0.0015(7) C9 0.0114(7) 0.0119(10) 0.0138(7) 0.0002(7) 0.0035(6) 0.0028(7) C10 0.0138(8) 0.0129(10) 0.0125(7) 0.0008(7) 0.0045(6) 0.0019(7) C11 0.0152(7) 0.0147(10) 0.0122(7) -0.0005(8) 0.0026(6) 0.0017(8) C12 0.0115(7) 0.0154(11) 0.0152(8) -0.0007(8) 0.0036(6) 0.0018(8) C13 0.0137(7) 0.0171(12) 0.0171(7) -0.0019(8) 0.0015(6) -0.0040(8) C14 0.0221(8) 0.0325(12) 0.0183(8) -0.0017(12) 0.0004(6) -0.0062(12) _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 C12 1.6856(19) . ? O1 C1 1.355(2) . ? O1 H1O1 0.84(3) . ? N1 C11 1.296(2) . ? N1 N2 1.379(2) . ? N2 C12 1.357(2) . ? N2 H1N2 0.94(3) . ? N3 C12 1.339(2) . ? N3 C13 1.464(3) . ? N3 H1N3 0.91(3) . ? C1 C10 1.403(2) . ? C1 C2 1.411(3) . ? C2 C3 1.368(3) . ? C2 H2A 0.9500 . ? C3 C4 1.419(3) . ? C3 H3A 0.9500 . ? C4 C5 1.423(3) . ? C4 C9 1.432(2) . ? C5 C6 1.372(3) . ? C5 H5A 0.9500 . ? C6 C7 1.412(3) . ? C6 H6A 0.9500 . ? C7 C8 1.371(3) . ? C7 H7A 0.9500 . ? C8 C9 1.420(2) . ? C8 H8A 0.9500 . ? C9 C10 1.437(3) . ? C10 C11 1.453(3) . ? C11 H11A 0.9500 . ? C13 C14 1.520(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 106.1(19) . . ? C11 N1 N2 115.99(14) . . ? C12 N2 N1 120.78(15) . . ? C12 N2 H1N2 117.4(17) . . ? N1 N2 H1N2 121.1(18) . . ? C12 N3 C13 124.43(17) . . ? C12 N3 H1N3 117.0(17) . . ? C13 N3 H1N3 118.5(17) . . ? O1 C1 C10 122.55(17) . . ? O1 C1 C2 115.94(16) . . ? C10 C1 C2 121.50(17) . . ? C3 C2 C1 119.91(16) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 121.37(18) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C3 C4 C5 121.33(17) . . ? C3 C4 C9 119.23(17) . . ? C5 C4 C9 119.44(16) . . ? C6 C5 C4 121.48(19) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C5 C6 C7 118.83(19) . . ? C5 C6 H6A 120.6 . . ? C7 C6 H6A 120.6 . . ? C8 C7 C6 121.40(17) . . ? C8 C7 H7A 119.3 . . ? C6 C7 H7A 119.3 . . ? C7 C8 C9 121.31(17) . . ? C7 C8 H8A 119.3 . . ? C9 C8 H8A 119.3 . . ? C8 C9 C4 117.53(17) . . ? C8 C9 C10 123.23(16) . . ? C4 C9 C10 119.23(15) . . ? C1 C10 C9 118.75(16) . . ? C1 C10 C11 120.58(17) . . ? C9 C10 C11 120.64(15) . . ? N1 C11 C10 122.02(16) . . ? N1 C11 H11A 119.0 . . ? C10 C11 H11A 119.0 . . ? N3 C12 N2 116.47(16) . . ? N3 C12 S1 123.33(15) . . ? N2 C12 S1 120.20(13) . . ? N3 C13 C14 108.89(18) . . ? N3 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? N3 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 N1 N2 C12 -177.57(17) . . . . ? O1 C1 C2 C3 -178.89(17) . . . . ? C10 C1 C2 C3 0.9(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 179.26(18) . . . . ? C2 C3 C4 C9 0.0(3) . . . . ? C3 C4 C5 C6 -179.95(19) . . . . ? C9 C4 C5 C6 -0.7(3) . . . . ? C4 C5 C6 C7 0.8(3) . . . . ? C5 C6 C7 C8 -0.4(3) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? C7 C8 C9 C4 0.4(3) . . . . ? C7 C8 C9 C10 179.66(18) . . . . ? C3 C4 C9 C8 179.33(18) . . . . ? C5 C4 C9 C8 0.0(2) . . . . ? C3 C4 C9 C10 0.1(2) . . . . ? C5 C4 C9 C10 -179.24(17) . . . . ? O1 C1 C10 C9 178.91(17) . . . . ? C2 C1 C10 C9 -0.9(3) . . . . ? O1 C1 C10 C11 -2.6(3) . . . . ? C2 C1 C10 C11 177.62(17) . . . . ? C8 C9 C10 C1 -178.85(18) . . . . ? C4 C9 C10 C1 0.4(2) . . . . ? C8 C9 C10 C11 2.7(3) . . . . ? C4 C9 C10 C11 -178.10(16) . . . . ? N2 N1 C11 C10 -179.77(16) . . . . ? C1 C10 C11 N1 -0.2(3) . . . . ? C9 C10 C11 N1 178.28(17) . . . . ? C13 N3 C12 N2 -179.84(17) . . . . ? C13 N3 C12 S1 0.1(3) . . . . ? N1 N2 C12 N3 -3.3(3) . . . . ? N1 N2 C12 S1 176.81(14) . . . . ? C12 N3 C13 C14 -176.24(19) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.328 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.058