data_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H21 Br N O4 S' _chemical_formula_sum 'C23 H21 Br N O4 S' _chemical_formula_weight 487.38 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.503(2) _cell_length_b 11.062(2) _cell_length_c 12.012(2) _cell_angle_alpha 91.99(3) _cell_angle_beta 112.83(3) _cell_angle_gamma 116.73(3) _cell_volume 1111.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4099 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 1.973 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.5058 _exptl_absorpt_correction_T_max 0.6937 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker APEX II CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6145 _diffrn_reflns_av_R_equivalents 0.0132 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4099 _reflns_number_gt 3464 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material '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^)+(0.0550P)^2^+0.3199P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4099 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0909 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.001 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 0.39448(3) 1.31007(3) 0.39440(2) 0.05415(11) Uani 1 1 d . . . C1 C -0.4486(5) 0.8351(6) -0.0831(4) 0.1230(18) Uani 1 1 d . . . H1A H -0.4849 0.7999 -0.0228 0.123 Uiso 1 1 calc R . . H1B H -0.5377 0.7951 -0.1650 0.123 Uiso 1 1 calc R . . H1C H -0.4006 0.9351 -0.0636 0.123 Uiso 1 1 calc R . . C2 C -0.1966(3) 0.8508(3) 0.0268(2) 0.0587(7) Uani 1 1 d . . . C3 C -0.1638(3) 0.9274(3) 0.1358(3) 0.0583(7) Uani 1 1 d . . . H3 H -0.2382 0.9484 0.1405 0.070 Uiso 1 1 calc R . . C4 C -0.0186(3) 0.9736(3) 0.2394(2) 0.0505(6) Uani 1 1 d . . . H4 H 0.0033 1.0250 0.3139 0.061 Uiso 1 1 calc R . . C5 C 0.0946(3) 0.9450(2) 0.2344(2) 0.0388(5) Uani 1 1 d . . . C6 C 0.0589(3) 0.8684(3) 0.1217(2) 0.0530(6) Uani 1 1 d . . . H6 H 0.1335 0.8487 0.1155 0.064 Uiso 1 1 calc R . . C7 C -0.0851(4) 0.8219(3) 0.0198(3) 0.0668(8) Uani 1 1 d . . . H7 H -0.1078 0.7702 -0.0550 0.080 Uiso 1 1 calc R . . C8 C 0.2483(3) 0.9900(2) 0.3437(2) 0.0396(5) Uani 1 1 d . . . C9 C 0.2831(2) 1.0605(2) 0.47283(19) 0.0358(5) Uani 1 1 d . . . H9 H 0.1914 1.0682 0.4668 0.043 Uiso 1 1 calc R . . C10 C 0.4322(3) 1.2061(2) 0.5220(2) 0.0391(5) Uani 1 1 d . . . H10 H 0.5222 1.1948 0.5291 0.047 Uiso 1 1 calc R . . C11 C 0.4771(3) 1.2864(2) 0.6468(2) 0.0411(5) Uani 1 1 d . . . C12 C 0.3822(4) 1.3313(3) 0.6657(3) 0.0614(8) Uani 1 1 d . . . H12 H 0.2850 1.3096 0.5999 0.074 Uiso 1 1 calc R . . C13 C 0.4311(4) 1.4082(4) 0.7817(3) 0.0788(10) Uani 1 1 d . . . H13 H 0.3675 1.4398 0.7930 0.095 Uiso 1 1 calc R . . C14 C 0.5714(4) 1.4385(4) 0.8799(3) 0.0797(10) Uani 1 1 d . . . H14 H 0.6031 1.4901 0.9580 0.096 Uiso 1 1 calc R . . C15 C 0.6651(4) 1.3928(4) 0.8631(3) 0.0798(10) Uani 1 1 d . . . H15 H 0.7605 1.4126 0.9303 0.096 Uiso 1 1 calc R . . C16 C 0.6191(3) 1.3165(3) 0.7461(3) 0.0591(7) Uani 1 1 d . . . H16 H 0.6837 1.2861 0.7351 0.071 Uiso 1 1 calc R . . C17 C 0.1160(3) 0.6972(2) 0.4654(2) 0.0393(5) Uani 1 1 d . . . C18 C -0.0064(3) 0.6593(3) 0.3472(2) 0.0489(6) Uani 1 1 d . . . H18 H -0.0601 0.7092 0.3265 0.059 Uiso 1 1 calc R . . C19 C -0.0484(3) 0.5465(3) 0.2601(3) 0.0567(7) Uani 1 1 d . . . H19 H -0.1301 0.5217 0.1800 0.068 Uiso 1 1 calc R . . C20 C 0.0281(4) 0.4696(3) 0.2889(3) 0.0560(7) Uani 1 1 d . . . C21 C -0.0144(5) 0.3502(3) 0.1912(4) 0.0809(10) Uani 1 1 d . . . H21A H -0.1279 0.2998 0.1389 0.121 Uiso 1 1 calc R . . H21B H 0.0179 0.2884 0.2313 0.121 Uiso 1 1 calc R . . H21C H 0.0395 0.3866 0.1411 0.121 Uiso 1 1 calc R . . C22 C 0.1481(4) 0.5083(3) 0.4086(3) 0.0591(7) Uani 1 1 d . . . H22 H 0.2001 0.4570 0.4299 0.071 Uiso 1 1 calc R . . C23 C 0.1934(3) 0.6212(3) 0.4979(3) 0.0494(6) Uani 1 1 d . . . H23 H 0.2744 0.6455 0.5782 0.059 Uiso 1 1 calc R . . N1 N 0.3176(2) 0.98082(19) 0.56347(18) 0.0401(4) Uani 1 1 d . . . O1 O 0.0445(2) 0.86782(19) 0.54188(17) 0.0529(4) Uani 1 1 d . . . O2 O 0.2503(2) 0.8281(2) 0.69675(17) 0.0608(5) Uani 1 1 d . . . O3 O 0.3499(2) 0.9686(2) 0.33696(17) 0.0548(5) Uani 1 1 d . . . O4 O -0.3349(3) 0.7987(3) -0.0801(2) 0.0962(8) Uani 1 1 d . . . S1 S 0.17713(7) 0.84571(6) 0.57602(5) 0.04096(15) Uani 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 0.06235(19) 0.04747(17) 0.04857(17) 0.01436(12) 0.02267(13) 0.02639(13) C1 0.070(3) 0.173(5) 0.086(3) 0.017(3) -0.007(2) 0.068(3) C2 0.0469(15) 0.0667(18) 0.0387(14) 0.0022(12) 0.0041(12) 0.0240(14) C3 0.0446(14) 0.078(2) 0.0488(15) 0.0057(14) 0.0127(12) 0.0363(15) C4 0.0470(14) 0.0650(16) 0.0372(13) -0.0026(11) 0.0125(11) 0.0330(13) C5 0.0394(12) 0.0385(12) 0.0357(12) 0.0026(9) 0.0146(10) 0.0201(10) C6 0.0563(16) 0.0600(16) 0.0443(14) -0.0009(12) 0.0202(12) 0.0336(14) C7 0.0686(19) 0.081(2) 0.0364(14) -0.0104(13) 0.0129(13) 0.0369(17) C8 0.0404(12) 0.0377(12) 0.0401(12) 0.0021(10) 0.0162(10) 0.0215(10) C9 0.0311(11) 0.0378(12) 0.0354(11) 0.0023(9) 0.0117(9) 0.0183(10) C10 0.0386(12) 0.0393(12) 0.0382(12) 0.0057(10) 0.0150(10) 0.0208(10) C11 0.0389(12) 0.0354(12) 0.0383(12) 0.0019(10) 0.0151(10) 0.0130(10) C12 0.0525(16) 0.0713(19) 0.0508(16) -0.0081(14) 0.0142(13) 0.0331(15) C13 0.074(2) 0.092(2) 0.067(2) -0.0138(18) 0.0288(18) 0.043(2) C14 0.075(2) 0.084(2) 0.0519(18) -0.0180(16) 0.0255(17) 0.0233(19) C15 0.0595(19) 0.106(3) 0.0387(15) -0.0066(16) 0.0053(14) 0.0301(19) C16 0.0523(16) 0.0700(18) 0.0466(15) 0.0029(13) 0.0157(13) 0.0307(14) C17 0.0380(12) 0.0357(11) 0.0473(13) 0.0102(10) 0.0248(11) 0.0165(10) C18 0.0476(14) 0.0430(13) 0.0527(15) 0.0076(11) 0.0187(12) 0.0239(12) C19 0.0577(16) 0.0490(15) 0.0511(15) 0.0010(12) 0.0216(13) 0.0206(13) C20 0.0672(18) 0.0412(14) 0.0698(18) 0.0110(13) 0.0457(16) 0.0229(13) C21 0.111(3) 0.0561(18) 0.091(2) 0.0062(17) 0.066(2) 0.0386(19) C22 0.0718(19) 0.0510(15) 0.083(2) 0.0241(15) 0.0489(17) 0.0405(15) C23 0.0493(14) 0.0488(14) 0.0576(15) 0.0164(12) 0.0275(12) 0.0276(12) N1 0.0355(10) 0.0358(10) 0.0419(10) 0.0070(8) 0.0131(8) 0.0162(8) O1 0.0445(10) 0.0546(10) 0.0637(11) 0.0020(9) 0.0295(9) 0.0248(8) O2 0.0698(13) 0.0630(12) 0.0432(10) 0.0156(9) 0.0244(9) 0.0293(10) O3 0.0450(10) 0.0693(12) 0.0515(10) -0.0029(9) 0.0160(8) 0.0361(9) O4 0.0667(14) 0.128(2) 0.0480(12) -0.0087(13) -0.0084(10) 0.0452(16) S1 0.0407(3) 0.0427(3) 0.0396(3) 0.0066(2) 0.0198(3) 0.0200(3) _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 C10 1.973(2) . ? C1 O4 1.411(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O4 1.356(3) . ? C2 C3 1.366(4) . ? C2 C7 1.375(4) . ? C3 C4 1.385(4) . ? C3 H3 0.9300 . ? C4 C5 1.381(3) . ? C4 H4 0.9300 . ? C5 C6 1.391(3) . ? C5 C8 1.471(3) . ? C6 C7 1.367(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O3 1.223(3) . ? C8 C9 1.539(3) . ? C9 N1 1.463(3) . ? C9 C10 1.530(3) . ? C9 H9 0.9800 . ? C10 C11 1.496(3) . ? C10 H10 0.9800 . ? C11 C12 1.380(4) . ? C11 C16 1.380(4) . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 C14 1.362(5) . ? C13 H13 0.9300 . ? C14 C15 1.364(5) . ? C14 H14 0.9300 . ? C15 C16 1.394(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.378(4) . ? C17 C23 1.383(3) . ? C17 S1 1.765(2) . ? C18 C19 1.379(4) . ? C18 H18 0.9300 . ? C19 C20 1.382(4) . ? C19 H19 0.9300 . ? C20 C22 1.380(4) . ? C20 C21 1.508(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.383(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? N1 S1 1.624(2) . ? O1 S1 1.4276(18) . ? O2 S1 1.421(2) . ? 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 O4 C1 H1A 109.5 . . ? O4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O4 C2 C3 124.6(3) . . ? O4 C2 C7 115.3(3) . . ? C3 C2 C7 120.1(2) . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 121.5(2) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.0(2) . . ? C4 C5 C8 122.6(2) . . ? C6 C5 C8 119.4(2) . . ? C7 C6 C5 120.5(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C2 120.6(2) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? O3 C8 C5 122.0(2) . . ? O3 C8 C9 117.6(2) . . ? C5 C8 C9 120.42(19) . . ? N1 C9 C10 106.55(17) . . ? N1 C9 C8 110.76(17) . . ? C10 C9 C8 109.90(19) . . ? N1 C9 H9 109.9 . . ? C10 C9 H9 109.9 . . ? C8 C9 H9 109.9 . . ? C11 C10 C9 115.0(2) . . ? C11 C10 Br1 110.81(15) . . ? C9 C10 Br1 107.10(15) . . ? C11 C10 H10 107.9 . . ? C9 C10 H10 107.9 . . ? Br1 C10 H10 107.9 . . ? C12 C11 C16 119.1(2) . . ? C12 C11 C10 122.5(2) . . ? C16 C11 C10 118.3(2) . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.6(3) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.7(3) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C18 C17 C23 120.7(2) . . ? C18 C17 S1 119.88(18) . . ? C23 C17 S1 119.41(19) . . ? C17 C18 C19 119.3(2) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C20 121.5(3) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C22 C20 C19 117.9(2) . . ? C22 C20 C21 121.1(3) . . ? C19 C20 C21 120.9(3) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 C23 121.9(3) . . ? C20 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? C17 C23 C22 118.7(3) . . ? C17 C23 H23 120.7 . . ? C22 C23 H23 120.7 . . ? C9 N1 S1 122.26(15) . . ? C2 O4 C1 118.3(3) . . ? O2 S1 O1 120.41(12) . . ? O2 S1 N1 105.71(12) . . ? O1 S1 N1 107.00(11) . . ? O2 S1 C17 107.60(12) . . ? O1 S1 C17 107.42(12) . . ? N1 S1 C17 108.22(11) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.561 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.053