data_mah1mnph_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Br N3 O S' _chemical_formula_weight 288.17 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' 'Br' 'Br' -0.2901 2.4595 '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 8.37760(10) _cell_length_b 6.20100(10) _cell_length_c 21.1050(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.5520(10) _cell_angle_gamma 90.00 _cell_volume 1092.94(3) _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 0.45 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.751 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 3.928 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.2727 _exptl_absorpt_correction_T_max 0.7625 _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 22785 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 35.17 _reflns_number_total 4831 _reflns_number_gt 3856 _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^)+(0.0221P)^2^+0.8634P] 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 4831 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0694 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.002 _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 Br1 Br 0.325997(19) 0.52891(3) 0.261749(7) 0.02172(5) Uani 1 1 d . . . S2 S 1.02742(5) -0.02858(6) 0.63174(2) 0.02126(8) Uani 1 1 d . . . O1 O 0.70308(14) 0.79122(19) 0.50511(6) 0.0206(2) Uani 1 1 d . . . N1 N 0.81176(15) 0.3848(2) 0.51377(6) 0.0157(2) Uani 1 1 d . . . N2 N 0.88851(16) 0.2049(2) 0.53985(6) 0.0178(2) Uani 1 1 d . . . N3 N 0.99562(16) 0.3992(2) 0.62610(6) 0.0171(2) Uani 1 1 d . . . C1 C 0.61682(17) 0.7238(2) 0.45101(7) 0.0145(2) Uani 1 1 d . . . C2 C 0.51142(18) 0.8689(2) 0.41976(8) 0.0187(3) Uani 1 1 d . . . H2A H 0.4987 1.0088 0.4370 0.022 Uiso 1 1 calc R . . C3 C 0.42473(18) 0.8111(2) 0.36369(7) 0.0177(3) Uani 1 1 d . . . H3A H 0.3537 0.9113 0.3422 0.021 Uiso 1 1 calc R . . C4 C 0.44242(17) 0.6057(3) 0.33910(7) 0.0164(3) Uani 1 1 d . . . C5 C 0.54324(17) 0.4567(2) 0.37074(7) 0.0168(3) Uani 1 1 d . . . H5A H 0.5524 0.3155 0.3540 0.020 Uiso 1 1 calc R . . C6 C 0.63165(17) 0.5141(2) 0.42740(7) 0.0144(2) Uani 1 1 d . . . C7 C 0.73102(17) 0.3502(2) 0.46023(7) 0.0164(3) Uani 1 1 d . . . H7A H 0.7366 0.2116 0.4414 0.020 Uiso 1 1 calc R . . C8 C 0.96802(17) 0.2088(2) 0.59850(7) 0.0153(3) Uani 1 1 d . . . C9 C 1.0821(2) 0.4251(3) 0.68817(8) 0.0215(3) Uani 1 1 d . . . H9A H 1.0869 0.5784 0.6994 0.032 Uiso 1 1 calc R . . H9B H 1.1910 0.3687 0.6868 0.032 Uiso 1 1 calc R . . H9C H 1.0266 0.3457 0.7200 0.032 Uiso 1 1 calc R . . H1N3 H 0.967(3) 0.502(3) 0.6079(11) 0.022(5) Uiso 1 1 d . . . H1N2 H 0.862(3) 0.086(4) 0.5271(11) 0.027(6) Uiso 1 1 d . . . H1O1 H 0.752(3) 0.699(5) 0.5199(12) 0.047(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 Br1 0.02343(8) 0.02415(8) 0.01614(8) -0.00118(6) -0.00742(5) -0.00061(6) S2 0.02866(19) 0.01404(16) 0.01976(18) 0.00101(14) -0.00644(14) 0.00511(14) O1 0.0267(6) 0.0143(5) 0.0189(5) -0.0040(4) -0.0097(4) 0.0040(4) N1 0.0163(5) 0.0130(6) 0.0172(6) 0.0014(5) -0.0014(4) 0.0023(4) N2 0.0229(6) 0.0117(6) 0.0175(6) 0.0000(5) -0.0058(5) 0.0036(4) N3 0.0215(6) 0.0136(6) 0.0151(6) 0.0011(5) -0.0047(4) 0.0010(5) C1 0.0176(6) 0.0149(6) 0.0105(6) -0.0008(5) -0.0019(5) 0.0004(5) C2 0.0215(7) 0.0138(7) 0.0202(7) 0.0001(5) -0.0023(5) 0.0032(5) C3 0.0174(6) 0.0175(7) 0.0177(7) 0.0030(5) -0.0025(5) 0.0024(5) C4 0.0161(6) 0.0188(7) 0.0137(6) -0.0007(5) -0.0029(5) -0.0015(5) C5 0.0195(6) 0.0149(6) 0.0155(6) -0.0012(5) -0.0020(5) 0.0008(5) C6 0.0151(6) 0.0140(6) 0.0137(6) 0.0011(5) -0.0010(4) 0.0011(5) C7 0.0198(6) 0.0140(6) 0.0146(6) -0.0004(5) -0.0024(5) 0.0020(5) C8 0.0156(6) 0.0147(6) 0.0155(7) 0.0003(5) -0.0003(5) 0.0022(5) C9 0.0261(7) 0.0186(7) 0.0185(7) -0.0018(6) -0.0065(6) 0.0003(6) _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 Br1 C4 1.8949(14) . ? S2 C8 1.6884(15) . ? O1 C1 1.3673(18) . ? O1 H1O1 0.76(3) . ? N1 C7 1.2879(19) . ? N1 N2 1.3801(17) . ? N2 C8 1.3585(19) . ? N2 H1N2 0.81(2) . ? N3 C8 1.329(2) . ? N3 C9 1.455(2) . ? N3 H1N3 0.77(2) . ? C1 C2 1.390(2) . ? C1 C6 1.402(2) . ? C2 C3 1.386(2) . ? C2 H2A 0.9500 . ? C3 C4 1.387(2) . ? C3 H3A 0.9500 . ? C4 C5 1.387(2) . ? C5 C6 1.402(2) . ? C5 H5A 0.9500 . ? C6 C7 1.454(2) . ? C7 H7A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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(2) . . ? C7 N1 N2 114.27(13) . . ? C8 N2 N1 121.90(13) . . ? C8 N2 H1N2 114.8(16) . . ? N1 N2 H1N2 119.9(16) . . ? C8 N3 C9 123.35(13) . . ? C8 N3 H1N3 118.6(16) . . ? C9 N3 H1N3 118.0(17) . . ? O1 C1 C2 118.19(13) . . ? O1 C1 C6 121.63(13) . . ? C2 C1 C6 120.18(13) . . ? C3 C2 C1 120.54(14) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C2 C3 C4 119.52(13) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C5 C4 C3 120.69(13) . . ? C5 C4 Br1 119.97(11) . . ? C3 C4 Br1 119.34(11) . . ? C4 C5 C6 120.13(14) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C5 C6 C1 118.88(13) . . ? C5 C6 C7 118.22(13) . . ? C1 C6 C7 122.86(13) . . ? N1 C7 C6 122.86(14) . . ? N1 C7 H7A 118.6 . . ? C6 C7 H7A 118.6 . . ? N3 C8 N2 118.09(13) . . ? N3 C8 S2 123.86(11) . . ? N2 C8 S2 118.05(11) . . ? 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 . . ? 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 -174.56(14) . . . . ? O1 C1 C2 C3 178.02(14) . . . . ? C6 C1 C2 C3 -2.6(2) . . . . ? C1 C2 C3 C4 0.7(2) . . . . ? C2 C3 C4 C5 1.4(2) . . . . ? C2 C3 C4 Br1 -179.06(12) . . . . ? C3 C4 C5 C6 -1.5(2) . . . . ? Br1 C4 C5 C6 178.91(11) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? C4 C5 C6 C7 177.65(14) . . . . ? O1 C1 C6 C5 -178.23(14) . . . . ? C2 C1 C6 C5 2.4(2) . . . . ? O1 C1 C6 C7 3.9(2) . . . . ? C2 C1 C6 C7 -175.51(14) . . . . ? N2 N1 C7 C6 175.11(14) . . . . ? C5 C6 C7 N1 -177.27(14) . . . . ? C1 C6 C7 N1 0.7(2) . . . . ? C9 N3 C8 N2 -178.76(14) . . . . ? C9 N3 C8 S2 0.7(2) . . . . ? N1 N2 C8 N3 -11.9(2) . . . . ? N1 N2 C8 S2 168.60(11) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 35.17 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.683 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.103