data_k76h _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Br N O3 S' _chemical_formula_weight 380.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.252(2) _cell_length_b 7.4707(15) _cell_length_c 20.115(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.217(6) _cell_angle_gamma 90.00 _cell_volume 1516.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1432 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 5.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker IuS microfocus' _diffrn_radiation_monochromator 'Quazar MX Optics' _diffrn_measurement_device_type 'Bruker APEX II CCD detector' _diffrn_measurement_method 'w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 17720 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.47 _diffrn_reflns_theta_max 65.21 _reflns_number_total 2527 _reflns_number_gt 2432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0428P)^2^+2.8282P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2527 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Br Br 0.41250(4) 0.60333(5) 0.063654(15) 0.03967(15) Uani 1 1 d . . . S S 0.40633(7) 0.54231(10) 0.38217(3) 0.02732(19) Uani 1 1 d . . . O1 O 0.58871(19) 0.7684(3) 0.31729(10) 0.0278(4) Uani 1 1 d . . . O2 O 0.3095(2) 0.4099(3) 0.38690(11) 0.0347(5) Uani 1 1 d . . . O3 O 0.3943(2) 0.7144(3) 0.41159(10) 0.0334(5) Uani 1 1 d . . . N N 0.5516(2) 0.4634(3) 0.41564(12) 0.0272(5) Uani 1 1 d . . . C1 C 0.4045(3) 0.5680(4) 0.29390(14) 0.0261(6) Uani 1 1 d . . . C2 C 0.3078(3) 0.4825(4) 0.24751(16) 0.0296(6) Uani 1 1 d . . . H2 H 0.242(4) 0.416(5) 0.2625(19) 0.038(10) Uiso 1 1 d . . . C3 C 0.3077(3) 0.4954(4) 0.17880(16) 0.0324(7) Uani 1 1 d . . . H3 H 0.243(3) 0.445(5) 0.1488(17) 0.027(8) Uiso 1 1 d . . . C4 C 0.4061(3) 0.5926(4) 0.15739(15) 0.0304(7) Uani 1 1 d . . . C5 C 0.5021(3) 0.6824(4) 0.20195(15) 0.0293(6) Uani 1 1 d . . . H5 H 0.567(3) 0.751(5) 0.1883(17) 0.033(9) Uiso 1 1 d . . . C6 C 0.5003(3) 0.6708(4) 0.27073(14) 0.0266(6) Uani 1 1 d . . . C7 C 0.7196(3) 0.7043(4) 0.33241(14) 0.0276(6) Uani 1 1 d . . . C8 C 0.8073(3) 0.7405(5) 0.28969(16) 0.0333(7) Uani 1 1 d . . . H8 H 0.778(3) 0.803(5) 0.2522(19) 0.032(9) Uiso 1 1 d . . . C9 C 0.9368(3) 0.6815(5) 0.30737(18) 0.0391(8) Uani 1 1 d . . . H9 H 0.995(4) 0.704(5) 0.280(2) 0.048(11) Uiso 1 1 d . . . C10 C 0.9775(3) 0.5910(5) 0.36799(18) 0.0379(8) Uani 1 1 d . . . H10 H 1.054(4) 0.554(5) 0.380(2) 0.041(10) Uiso 1 1 d . . . C11 C 0.8881(3) 0.5585(5) 0.41021(17) 0.0347(7) Uani 1 1 d . . . H11 H 0.914(3) 0.498(5) 0.4530(19) 0.038(9) Uiso 1 1 d . . . C12 C 0.7576(3) 0.6158(4) 0.39359(15) 0.0294(7) Uani 1 1 d . . . C13 C 0.6609(3) 0.5874(4) 0.44114(15) 0.0302(7) Uani 1 1 d . . . H13A H 0.711(4) 0.533(5) 0.485(2) 0.043(10) Uiso 1 1 d . . . H13B H 0.624(3) 0.698(5) 0.4507(16) 0.024(8) Uiso 1 1 d . . . C14 C 0.5870(3) 0.2926(4) 0.39002(15) 0.0303(7) Uani 1 1 d . . . H14 H 0.600(3) 0.297(5) 0.3455(18) 0.032(9) Uiso 1 1 d . . . C15 C 0.5304(4) 0.1245(5) 0.4126(2) 0.0412(8) Uani 1 1 d . . . H15A H 0.471(4) 0.139(5) 0.442(2) 0.047(11) Uiso 1 1 d . . . H15B H 0.506(4) 0.034(6) 0.381(2) 0.043(10) Uiso 1 1 d . . . C16 C 0.6724(4) 0.1699(5) 0.43861(18) 0.0393(8) Uani 1 1 d . . . H16A H 0.739(3) 0.110(4) 0.4178(18) 0.030(9) Uiso 1 1 d . . . H16B H 0.695(4) 0.206(5) 0.485(2) 0.040(10) 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 Br 0.0490(2) 0.0489(3) 0.0209(2) -0.00483(13) 0.00547(15) -0.00158(15) S 0.0284(4) 0.0317(4) 0.0231(4) 0.0022(3) 0.0080(3) 0.0045(3) O1 0.0303(11) 0.0291(11) 0.0236(10) -0.0018(8) 0.0041(8) -0.0004(8) O2 0.0337(12) 0.0409(13) 0.0315(11) 0.0047(9) 0.0112(9) 0.0025(9) O3 0.0387(12) 0.0336(12) 0.0297(11) -0.0001(9) 0.0114(9) 0.0088(9) N 0.0312(13) 0.0279(13) 0.0231(12) 0.0013(10) 0.0058(10) 0.0040(10) C1 0.0276(15) 0.0299(15) 0.0211(14) 0.0021(12) 0.0050(11) 0.0041(12) C2 0.0273(15) 0.0308(16) 0.0308(16) 0.0004(13) 0.0051(12) -0.0005(13) C3 0.0309(16) 0.0338(17) 0.0303(16) -0.0033(13) -0.0009(13) -0.0012(13) C4 0.0363(17) 0.0334(17) 0.0216(15) -0.0016(12) 0.0053(12) 0.0028(13) C5 0.0314(16) 0.0326(17) 0.0243(15) 0.0008(13) 0.0058(12) -0.0006(13) C6 0.0285(15) 0.0267(15) 0.0241(14) 0.0002(12) 0.0032(12) 0.0026(12) C7 0.0281(15) 0.0278(15) 0.0261(15) -0.0061(12) 0.0026(12) -0.0028(12) C8 0.0345(17) 0.0377(18) 0.0272(16) 0.0012(14) 0.0041(13) -0.0094(14) C9 0.0326(18) 0.050(2) 0.0366(18) -0.0061(16) 0.0100(14) -0.0100(15) C10 0.0234(17) 0.045(2) 0.043(2) -0.0074(15) 0.0010(14) -0.0004(14) C11 0.0361(17) 0.0353(17) 0.0311(17) -0.0020(14) 0.0015(13) 0.0002(14) C12 0.0317(16) 0.0303(16) 0.0253(15) -0.0041(12) 0.0030(12) -0.0044(12) C13 0.0345(17) 0.0333(17) 0.0222(15) -0.0023(13) 0.0037(13) 0.0027(13) C14 0.0344(16) 0.0349(17) 0.0232(15) -0.0017(13) 0.0093(12) 0.0058(13) C15 0.051(2) 0.0307(18) 0.046(2) -0.0012(16) 0.0201(18) 0.0039(15) C16 0.049(2) 0.0391(19) 0.0305(17) 0.0024(15) 0.0085(15) 0.0142(16) _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 Br C4 1.900(3) . ? S O2 1.417(2) . ? S O3 1.429(2) . ? S N 1.632(2) . ? S C1 1.783(3) . ? O1 C6 1.389(4) . ? O1 C7 1.406(4) . ? N C14 1.446(4) . ? N C13 1.474(4) . ? C1 C2 1.390(4) . ? C1 C6 1.391(4) . ? C2 C3 1.385(4) . ? C2 H2 0.93(4) . ? C3 C4 1.373(5) . ? C3 H3 0.89(4) . ? C4 C5 1.382(5) . ? C5 C6 1.389(4) . ? C5 H5 0.92(4) . ? C7 C8 1.376(4) . ? C7 C12 1.391(4) . ? C8 C9 1.384(5) . ? C8 H8 0.89(4) . ? C9 C10 1.392(5) . ? C9 H9 0.90(4) . ? C10 C11 1.377(5) . ? C10 H10 0.83(4) . ? C11 C12 1.388(5) . ? C11 H11 0.97(4) . ? C12 C13 1.510(4) . ? C13 H13A 1.02(4) . ? C13 H13B 0.94(3) . ? C14 C15 1.488(5) . ? C14 C16 1.503(5) . ? C14 H14 0.93(4) . ? C15 C16 1.496(6) . ? C15 H15A 0.92(4) . ? C15 H15B 0.93(4) . ? C16 H16A 0.97(4) . ? C16 H16B 0.95(4) . ? 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 S O3 119.16(13) . . ? O2 S N 108.61(13) . . ? O3 S N 107.06(13) . . ? O2 S C1 104.97(14) . . ? O3 S C1 109.21(13) . . ? N S C1 107.30(13) . . ? C6 O1 C7 116.8(2) . . ? C14 N C13 117.0(2) . . ? C14 N S 116.1(2) . . ? C13 N S 119.9(2) . . ? C2 C1 C6 119.4(3) . . ? C2 C1 S 120.0(2) . . ? C6 C1 S 120.7(2) . . ? C3 C2 C1 120.8(3) . . ? C3 C2 H2 119(2) . . ? C1 C2 H2 120(2) . . ? C4 C3 C2 118.6(3) . . ? C4 C3 H3 120(2) . . ? C2 C3 H3 121(2) . . ? C3 C4 C5 122.1(3) . . ? C3 C4 Br 119.4(2) . . ? C5 C4 Br 118.5(2) . . ? C4 C5 C6 118.8(3) . . ? C4 C5 H5 123(2) . . ? C6 C5 H5 118(2) . . ? O1 C6 C5 121.1(3) . . ? O1 C6 C1 118.6(2) . . ? C5 C6 C1 120.2(3) . . ? C8 C7 C12 122.3(3) . . ? C8 C7 O1 120.2(3) . . ? C12 C7 O1 117.4(3) . . ? C7 C8 C9 118.7(3) . . ? C7 C8 H8 118(2) . . ? C9 C8 H8 123(2) . . ? C8 C9 C10 120.3(3) . . ? C8 C9 H9 120(3) . . ? C10 C9 H9 120(3) . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 117(3) . . ? C9 C10 H10 123(3) . . ? C10 C11 C12 121.0(3) . . ? C10 C11 H11 121(2) . . ? C12 C11 H11 117(2) . . ? C11 C12 C7 117.8(3) . . ? C11 C12 C13 121.2(3) . . ? C7 C12 C13 121.0(3) . . ? N C13 C12 114.3(2) . . ? N C13 H13A 107(2) . . ? C12 C13 H13A 108(2) . . ? N C13 H13B 108(2) . . ? C12 C13 H13B 109.7(19) . . ? H13A C13 H13B 110(3) . . ? N C14 C15 120.0(3) . . ? N C14 C16 117.4(3) . . ? C15 C14 C16 60.0(2) . . ? N C14 H14 114(2) . . ? C15 C14 H14 117(2) . . ? C16 C14 H14 119(2) . . ? C14 C15 C16 60.5(2) . . ? C14 C15 H15A 115(3) . . ? C16 C15 H15A 117(3) . . ? C14 C15 H15B 118(2) . . ? C16 C15 H15B 122(2) . . ? H15A C15 H15B 114(4) . . ? C15 C16 C14 59.5(2) . . ? C15 C16 H16A 117(2) . . ? C14 C16 H16A 112(2) . . ? C15 C16 H16B 117(2) . . ? C14 C16 H16B 118(2) . . ? H16A C16 H16B 119(3) . . ? 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 O2 S N C14 53.3(2) . . . . ? O3 S N C14 -176.9(2) . . . . ? C1 S N C14 -59.7(2) . . . . ? O2 S N C13 -156.8(2) . . . . ? O3 S N C13 -26.9(2) . . . . ? C1 S N C13 90.3(2) . . . . ? O2 S C1 C2 7.7(3) . . . . ? O3 S C1 C2 -121.1(3) . . . . ? N S C1 C2 123.1(2) . . . . ? O2 S C1 C6 -171.3(2) . . . . ? O3 S C1 C6 59.8(3) . . . . ? N S C1 C6 -55.9(3) . . . . ? C6 C1 C2 C3 1.5(5) . . . . ? S C1 C2 C3 -177.6(2) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? C2 C3 C4 C5 -2.3(5) . . . . ? C2 C3 C4 Br 177.2(2) . . . . ? C3 C4 C5 C6 1.4(5) . . . . ? Br C4 C5 C6 -178.1(2) . . . . ? C7 O1 C6 C5 -76.6(3) . . . . ? C7 O1 C6 C1 106.9(3) . . . . ? C4 C5 C6 O1 -175.5(3) . . . . ? C4 C5 C6 C1 1.0(5) . . . . ? C2 C1 C6 O1 174.2(3) . . . . ? S C1 C6 O1 -6.8(4) . . . . ? C2 C1 C6 C5 -2.4(4) . . . . ? S C1 C6 C5 176.7(2) . . . . ? C6 O1 C7 C8 80.7(3) . . . . ? C6 O1 C7 C12 -103.6(3) . . . . ? C12 C7 C8 C9 2.1(5) . . . . ? O1 C7 C8 C9 177.5(3) . . . . ? C7 C8 C9 C10 -1.4(5) . . . . ? C8 C9 C10 C11 0.7(5) . . . . ? C9 C10 C11 C12 -0.5(5) . . . . ? C10 C11 C12 C7 1.1(5) . . . . ? C10 C11 C12 C13 -177.3(3) . . . . ? C8 C7 C12 C11 -1.9(5) . . . . ? O1 C7 C12 C11 -177.4(3) . . . . ? C8 C7 C12 C13 176.5(3) . . . . ? O1 C7 C12 C13 1.0(4) . . . . ? C14 N C13 C12 49.8(4) . . . . ? S N C13 C12 -99.9(3) . . . . ? C11 C12 C13 N -114.0(3) . . . . ? C7 C12 C13 N 67.6(4) . . . . ? C13 N C14 C15 131.4(3) . . . . ? S N C14 C15 -77.7(3) . . . . ? C13 N C14 C16 62.0(4) . . . . ? S N C14 C16 -147.2(3) . . . . ? N C14 C15 C16 -106.3(3) . . . . ? N C14 C16 C15 110.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 65.21 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.375 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.074