# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Han, Jianlin' _publ_contact_author_email hanjl@nju.edu.cn _publ_section_title ; Tandem copper-catalyzed aminobromination/olefination process: an efficient access to \^I+-,\^I^2^-unsaturated vicinal haloamino ketones and esters ; loop_ _publ_author_name 'Hao Sun' 'Guangqian Zhang' 'Sanjun Zhi' 'Jianlin Han' 'Guigen Li' ; Yi Pan ; # Attachment '- 2aa.cif' data_ss _database_code_depnum_ccdc_archive 'CCDC 724865' #TrackingRef '- 2aa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C24 H22 Br N O4 S), H2 O' _chemical_formula_sum 'C96 H90 Br4 N4 O17 S4' _chemical_formula_weight 2019.60 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 39.577(12) _cell_length_b 6.966(2) _cell_length_c 18.429(6) _cell_angle_alpha 90.00 _cell_angle_beta 116.465(4) _cell_angle_gamma 90.00 _cell_volume 4548(2) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2067 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 23.51 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2068 _exptl_absorpt_coefficient_mu 1.931 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.613 _exptl_absorpt_correction_T_max 0.684 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11686 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4464 _reflns_number_gt 3100 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _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^)+(0.05P)^2^+1.55P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4464 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 Br1 Br 0.295927(12) 0.05145(6) 0.40047(3) 0.04653(14) Uani 1 1 d . . . C1 C 0.29953(11) 0.1287(6) 0.2527(2) 0.0422(9) Uani 1 1 d . . . C2 C 0.32185(13) 0.0664(6) 0.2167(3) 0.0491(10) Uani 1 1 d . . . H2 H 0.3478 0.0558 0.2474 0.059 Uiso 1 1 calc R . . C3 C 0.30534(11) 0.0201(6) 0.1347(2) 0.0430(9) Uani 1 1 d . . . H3 H 0.3203 -0.0215 0.1106 0.052 Uiso 1 1 calc R . . C4 C 0.26649(11) 0.0361(6) 0.0888(2) 0.0418(9) Uani 1 1 d . . . C5 C 0.24417(12) 0.0983(6) 0.1248(3) 0.0448(10) Uani 1 1 d . . . H5 H 0.2182 0.1090 0.0941 0.054 Uiso 1 1 calc R . . C6 C 0.26069(12) 0.1446(6) 0.2068(2) 0.0470(10) Uani 1 1 d . . . H6 H 0.2458 0.1863 0.2309 0.056 Uiso 1 1 calc R . . C7 C 0.21083(10) -0.0310(6) -0.0220(2) 0.0446(9) Uani 1 1 d . . . H7B H 0.2020 -0.1194 0.0058 0.054 Uiso 1 1 calc R . . H7C H 0.2022 -0.0716 -0.0772 0.054 Uiso 1 1 calc R . . H7A H 0.2012 0.0949 -0.0210 0.054 Uiso 1 1 calc R . . C8 C 0.31643(12) 0.1816(6) 0.3380(2) 0.0453(9) Uani 1 1 d . . . C9 C 0.34503(11) 0.2951(6) 0.3766(2) 0.0451(10) Uani 1 1 d . . . C10 C 0.35988(12) 0.3588(7) 0.4634(2) 0.0449(9) Uani 1 1 d . . . C11 C 0.37633(12) 0.2230(6) 0.5317(2) 0.0491(10) Uani 1 1 d . . . C12 C 0.38300(11) 0.0296(6) 0.5219(2) 0.0443(9) Uani 1 1 d . . . H12 H 0.3769 -0.0173 0.4703 0.053 Uiso 1 1 calc R . . C13 C 0.39824(12) -0.0902(6) 0.5865(3) 0.0547(12) Uani 1 1 d . . . H13 H 0.4019 -0.2190 0.5789 0.066 Uiso 1 1 calc R . . C14 C 0.40802(11) -0.0226(6) 0.6618(2) 0.0444(9) Uani 1 1 d . . . H14 H 0.4183 -0.1055 0.7059 0.053 Uiso 1 1 calc R . . C15 C 0.40284(11) 0.1697(6) 0.6741(2) 0.0443(10) Uani 1 1 d . . . H15 H 0.4101 0.2161 0.7263 0.053 Uiso 1 1 calc R . . C16 C 0.38673(12) 0.2919(6) 0.6081(2) 0.0465(10) Uani 1 1 d . . . H16 H 0.3830 0.4206 0.6159 0.056 Uiso 1 1 calc R . . C17 C 0.43397(11) 0.5036(6) 0.4352(2) 0.0412(9) Uani 1 1 d . . . C18 C 0.43753(12) 0.6986(6) 0.4272(2) 0.0488(10) Uani 1 1 d . . . H18 H 0.4246 0.7565 0.3767 0.059 Uiso 1 1 calc R . . C19 C 0.45972(11) 0.8060(6) 0.4923(2) 0.0475(10) Uani 1 1 d . . . H19 H 0.4626 0.9362 0.4855 0.057 Uiso 1 1 calc R . . C20 C 0.47834(11) 0.7247(6) 0.5694(3) 0.0493(10) Uani 1 1 d . . . C21 C 0.47452(11) 0.5302(6) 0.5760(2) 0.0452(9) Uani 1 1 d . . . H21 H 0.4875 0.4722 0.6264 0.054 Uiso 1 1 calc R . . C22 C 0.45216(11) 0.4183(6) 0.5105(3) 0.0469(10) Uani 1 1 d . . . H22 H 0.4494 0.2877 0.5168 0.056 Uiso 1 1 calc R . . C23 C 0.34125(12) 0.5751(6) 0.2914(2) 0.0463(10) Uani 1 1 d . . . H23A H 0.3148 0.5503 0.2603 0.069 Uiso 1 1 calc R . . H23B H 0.3514 0.6219 0.2563 0.069 Uiso 1 1 calc R . . H23C H 0.3449 0.6696 0.3322 0.069 Uiso 1 1 calc R . . C24 C 0.50163(12) 0.8510(7) 0.6414(3) 0.0545(11) Uani 1 1 d . . . H24A H 0.5009 0.8002 0.6891 0.082 Uiso 1 1 calc R . . H24B H 0.4915 0.9788 0.6316 0.082 Uiso 1 1 calc R . . H24C H 0.5273 0.8541 0.6492 0.082 Uiso 1 1 calc R . . N1 N 0.36053(10) 0.3977(4) 0.3303(2) 0.0431(8) Uani 1 1 d . . . O1 O 0.24831(8) -0.0267(4) 0.01437(16) 0.0506(7) Uani 1 1 d . . . O2 O 0.35859(8) 0.5299(4) 0.47563(18) 0.0511(7) Uani 1 1 d . . . O3 O 0.41241(8) 0.1626(4) 0.37169(16) 0.0490(7) Uani 1 1 d . . . O4 O 0.40888(8) 0.4356(4) 0.28207(17) 0.0474(7) Uani 1 1 d . . . H5B H 0.4806 0.3298 0.7567 0.071 Uiso 0.25 1 d PR . . H5C H 0.5127 0.2553 0.7547 0.071 Uiso 0.25 1 d PR . . O5 O 0.5000 0.3567(11) 0.7500 0.0449(18) Uani 0.50 2 d SP . . S1 S 0.40467(3) 0.36317(17) 0.34992(7) 0.0488(3) 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 0.0437(2) 0.0412(2) 0.0476(2) -0.00475(19) 0.01398(17) -0.01739(19) C1 0.044(2) 0.046(2) 0.035(2) 0.0000(17) 0.0162(18) 0.0004(18) C2 0.049(2) 0.050(2) 0.042(2) -0.006(2) 0.0144(19) -0.005(2) C3 0.045(2) 0.040(2) 0.041(2) -0.0004(17) 0.0168(17) -0.0107(17) C4 0.042(2) 0.033(2) 0.042(2) 0.0101(18) 0.0122(17) 0.0087(17) C5 0.040(2) 0.043(3) 0.046(2) -0.0067(17) 0.0141(19) -0.0136(16) C6 0.045(2) 0.048(3) 0.043(2) -0.0142(19) 0.0153(19) -0.0059(18) C7 0.039(2) 0.039(2) 0.044(2) 0.0109(18) 0.0075(17) 0.0144(17) C8 0.055(2) 0.034(2) 0.039(2) -0.0004(17) 0.0144(19) -0.0040(18) C9 0.054(2) 0.033(2) 0.043(2) 0.0073(17) 0.016(2) 0.0076(18) C10 0.049(2) 0.044(3) 0.038(2) 0.0008(19) 0.0167(19) -0.0108(19) C11 0.059(3) 0.048(3) 0.031(2) -0.0014(17) 0.0115(19) -0.004(2) C12 0.041(2) 0.052(3) 0.037(2) -0.0039(19) 0.0138(16) 0.0002(19) C13 0.053(3) 0.042(3) 0.042(2) -0.0082(18) -0.003(2) 0.0126(18) C14 0.040(2) 0.043(2) 0.043(2) 0.0124(18) 0.0118(17) 0.0086(17) C15 0.040(2) 0.055(3) 0.036(2) -0.0075(18) 0.0142(17) -0.0026(18) C16 0.062(3) 0.029(2) 0.037(2) -0.0024(17) 0.0112(19) -0.0024(18) C17 0.0348(19) 0.045(2) 0.042(2) 0.0038(17) 0.0157(16) 0.0007(16) C18 0.051(2) 0.039(2) 0.040(2) 0.0061(18) 0.0055(19) -0.0092(19) C19 0.041(2) 0.043(2) 0.051(2) -0.001(2) 0.0142(19) -0.0145(18) C20 0.045(2) 0.049(3) 0.049(2) -0.013(2) 0.016(2) 0.0025(18) C21 0.041(2) 0.042(2) 0.046(2) 0.0032(19) 0.0130(18) 0.0053(18) C22 0.046(2) 0.043(3) 0.047(2) -0.0031(18) 0.0159(19) -0.0146(17) C23 0.048(2) 0.042(2) 0.040(2) 0.0184(17) 0.0119(19) 0.0123(18) C24 0.050(3) 0.056(3) 0.049(2) -0.016(2) 0.013(2) -0.010(2) N1 0.053(2) 0.0367(19) 0.0368(18) 0.0050(13) 0.0171(16) -0.0012(14) O1 0.0421(15) 0.0475(18) 0.0429(16) -0.0092(13) 0.0016(12) 0.0146(13) O2 0.0507(16) 0.0365(17) 0.0536(17) -0.0075(14) 0.0120(14) -0.0042(13) O3 0.0483(16) 0.0444(18) 0.0473(16) 0.0120(13) 0.0151(13) 0.0124(13) O4 0.0473(16) 0.0420(16) 0.0454(16) -0.0022(12) 0.0139(13) -0.0094(13) O5 0.054(5) 0.039(4) 0.042(4) 0.000 0.021(4) 0.000 S1 0.0435(6) 0.0455(6) 0.0493(6) 0.0037(5) 0.0134(5) 0.0026(5) _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 C8 1.908(4) . ? C1 C2 1.390(6) . ? C1 C6 1.390(6) . ? C1 C8 1.454(5) . ? C2 C3 1.390(5) . ? C2 H2 0.9300 . ? C3 C4 1.390(5) . ? C3 H3 0.9300 . ? C4 O1 1.308(5) . ? C4 C5 1.390(6) . ? C5 C6 1.390(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.328(5) . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C7 H7A 0.9600 . ? C8 C9 1.302(6) . ? C9 N1 1.443(5) . ? C9 C10 1.505(6) . ? C10 O2 1.218(5) . ? C10 C11 1.474(6) . ? C11 C16 1.367(5) . ? C11 C12 1.400(6) . ? C12 C13 1.356(6) . ? C12 H12 0.9300 . ? C13 C14 1.349(6) . ? C13 H13 0.9300 . ? C14 C15 1.389(6) . ? C14 H14 0.9300 . ? C15 C16 1.385(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.380(6) . ? C17 C22 1.381(6) . ? C17 S1 1.774(4) . ? C18 C19 1.353(5) . ? C18 H18 0.9300 . ? C19 C20 1.396(6) . ? C19 H19 0.9300 . ? C20 C21 1.375(6) . ? C20 C24 1.515(6) . ? C21 C22 1.377(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 N1 1.461(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? N1 S1 1.636(4) . ? O3 S1 1.448(3) . ? O4 S1 1.425(3) . ? O5 H5B 0.8499 . ? O5 H5C 0.8500 . ? 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 C2 C1 C6 120.0(4) . . ? C2 C1 C8 120.7(4) . . ? C6 C1 C8 119.3(4) . . ? C1 C2 C3 120.0(4) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 120.0(4) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? O1 C4 C5 115.8(3) . . ? O1 C4 C3 123.6(4) . . ? C5 C4 C3 120.0(4) . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.0(4) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O1 C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C7 H7A 109.5 . . ? H7B C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? C9 C8 C1 127.9(4) . . ? C9 C8 Br1 117.3(3) . . ? C1 C8 Br1 114.7(3) . . ? C8 C9 N1 118.2(4) . . ? C8 C9 C10 126.4(4) . . ? N1 C9 C10 114.5(3) . . ? O2 C10 C11 120.5(4) . . ? O2 C10 C9 117.2(4) . . ? C11 C10 C9 122.2(4) . . ? C16 C11 C12 118.9(4) . . ? C16 C11 C10 118.1(4) . . ? C12 C11 C10 123.0(4) . . ? C13 C12 C11 121.0(4) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 120.0(4) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.6(4) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 119.5(4) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C11 C16 C15 119.9(4) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C18 C17 C22 119.9(4) . . ? C18 C17 S1 120.4(3) . . ? C22 C17 S1 119.7(3) . . ? C19 C18 C17 120.4(4) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 121.2(4) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C21 C20 C19 117.4(4) . . ? C21 C20 C24 122.9(4) . . ? C19 C20 C24 119.7(4) . . ? C20 C21 C22 122.3(4) . . ? C20 C21 O5 118.1(3) . . ? C22 C21 O5 117.7(3) . . ? C20 C21 H21 118.9 . . ? C22 C21 H21 118.9 . . ? C21 C22 C17 118.7(4) . . ? C21 C22 H22 120.6 . . ? C17 C22 H22 120.6 . . ? N1 C23 H23A 109.5 . . ? N1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C9 N1 C23 116.2(3) . . ? C9 N1 S1 119.3(3) . . ? C23 N1 S1 120.4(3) . . ? C4 O1 C7 120.4(3) . . ? C21 O5 H5B 109.5 . . ? C21 O5 H5C 109.3 . . ? H5B O5 H5C 109.5 . . ? O4 S1 O3 119.43(19) . . ? O4 S1 N1 106.53(17) . . ? O3 S1 N1 106.04(17) . . ? O4 S1 C17 107.23(18) . . ? O3 S1 C17 108.21(18) . . ? N1 S1 C17 109.08(18) . . ? 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 C6 C1 C2 C3 0.0(6) . . . . ? C8 C1 C2 C3 -178.7(4) . . . . ? C1 C2 C3 C4 0.0(6) . . . . ? C2 C3 C4 O1 -171.2(4) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? O1 C4 C5 C6 171.9(4) . . . . ? C3 C4 C5 C6 0.0(6) . . . . ? C4 C5 C6 C1 0.0(6) . . . . ? C2 C1 C6 C5 0.0(7) . . . . ? C8 C1 C6 C5 178.7(4) . . . . ? C2 C1 C8 C9 48.9(7) . . . . ? C6 C1 C8 C9 -129.7(5) . . . . ? C2 C1 C8 Br1 -126.0(4) . . . . ? C6 C1 C8 Br1 55.3(5) . . . . ? C1 C8 C9 N1 6.3(7) . . . . ? Br1 C8 C9 N1 -178.9(3) . . . . ? C1 C8 C9 C10 174.9(4) . . . . ? Br1 C8 C9 C10 -10.3(6) . . . . ? C8 C9 C10 O2 -117.1(5) . . . . ? N1 C9 C10 O2 51.8(5) . . . . ? C8 C9 C10 C11 64.5(6) . . . . ? N1 C9 C10 C11 -126.6(4) . . . . ? O2 C10 C11 C16 6.0(6) . . . . ? C9 C10 C11 C16 -175.6(4) . . . . ? O2 C10 C11 C12 -171.5(4) . . . . ? C9 C10 C11 C12 6.9(7) . . . . ? C16 C11 C12 C13 2.4(6) . . . . ? C10 C11 C12 C13 179.9(4) . . . . ? C11 C12 C13 C14 -1.5(7) . . . . ? C12 C13 C14 C15 -0.4(7) . . . . ? C13 C14 C15 C16 1.4(6) . . . . ? C12 C11 C16 C15 -1.3(6) . . . . ? C10 C11 C16 C15 -179.0(4) . . . . ? C14 C15 C16 C11 -0.5(6) . . . . ? C22 C17 C18 C19 2.1(6) . . . . ? S1 C17 C18 C19 179.7(3) . . . . ? C17 C18 C19 C20 -2.5(7) . . . . ? C18 C19 C20 C21 2.7(6) . . . . ? C18 C19 C20 C24 -177.4(4) . . . . ? C19 C20 C21 C22 -2.5(6) . . . . ? C24 C20 C21 C22 177.6(4) . . . . ? C19 C20 C21 O5 -166.5(3) . . . . ? C24 C20 C21 O5 13.7(5) . . . . ? C20 C21 C22 C17 2.2(6) . . . . ? O5 C21 C22 C17 166.2(3) . . . . ? C18 C17 C22 C21 -1.9(6) . . . . ? S1 C17 C22 C21 -179.5(3) . . . . ? C8 C9 N1 C23 82.7(5) . . . . ? C10 C9 N1 C23 -87.2(4) . . . . ? C8 C9 N1 S1 -119.8(4) . . . . ? C10 C9 N1 S1 70.3(4) . . . . ? C5 C4 O1 C7 -0.9(5) . . . . ? C3 C4 O1 C7 170.6(4) . . . . ? C9 N1 S1 O4 163.5(3) . . . . ? C23 N1 S1 O4 -40.0(3) . . . . ? C9 N1 S1 O3 35.3(3) . . . . ? C23 N1 S1 O3 -168.2(3) . . . . ? C9 N1 S1 C17 -81.1(3) . . . . ? C23 N1 S1 C17 75.4(3) . . . . ? C18 C17 S1 O4 38.0(4) . . . . ? C22 C17 S1 O4 -144.4(3) . . . . ? C18 C17 S1 O3 168.1(3) . . . . ? C22 C17 S1 O3 -14.3(4) . . . . ? C18 C17 S1 N1 -77.0(4) . . . . ? C22 C17 S1 N1 100.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.305 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.061 # Attachment '- 5.cif' data_sh2 _database_code_depnum_ccdc_archive 'CCDC 772637' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H26 Br N O4 S' _chemical_formula_sum 'C25 H26 Br N O4 S' _chemical_formula_weight 516.44 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 14.2872(18) _cell_length_b 11.9099(15) _cell_length_c 16.8217(16) _cell_angle_alpha 90.00 _cell_angle_beta 121.648(8) _cell_angle_gamma 90.00 _cell_volume 2436.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3002 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 22.11 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.803 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6322 _exptl_absorpt_correction_T_max 0.6924 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13136 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4790 _reflns_number_gt 3504 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _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^)+(0.05P)^2^+1.99P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4790 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 Br1 Br 0.65986(4) -0.10750(4) 0.80638(3) 0.04728(16) Uani 1 1 d . . . C1 C 0.4712(4) 0.1123(4) 0.8069(3) 0.0469(11) Uani 1 1 d . . . H1 H 0.5285 0.1373 0.8645 0.056 Uiso 1 1 calc R . . C2 C 0.3632(3) 0.1247(4) 0.7838(3) 0.0401(10) Uani 1 1 d . . . H2 H 0.3479 0.1587 0.8255 0.048 Uiso 1 1 calc R . . C3 C 0.2778(4) 0.0860(4) 0.6979(3) 0.0428(10) Uani 1 1 d . . . C4 C 0.3005(4) 0.0365(4) 0.6357(3) 0.0457(11) Uani 1 1 d . . . H4 H 0.2431 0.0116 0.5781 0.055 Uiso 1 1 calc R . . C5 C 0.4087(4) 0.0238(4) 0.6583(3) 0.0457(11) Uani 1 1 d . . . H5 H 0.4237 -0.0104 0.6165 0.055 Uiso 1 1 calc R . . C6 C 0.4940(4) 0.0623(3) 0.7438(3) 0.0373(9) Uani 1 1 d . . . C7 C 0.6123(4) 0.0503(4) 0.7722(3) 0.0465(11) Uani 1 1 d . . . H7 H 0.6569 0.0971 0.8275 0.056 Uiso 1 1 calc R . . C8 C 0.6355(4) 0.0856(4) 0.6980(3) 0.0479(12) Uani 1 1 d . . . H8 H 0.5957 0.0336 0.6455 0.057 Uiso 1 1 calc R . . C9 C 0.7612(4) 0.0714(4) 0.7355(3) 0.0464(11) Uani 1 1 d . . . C10 C 0.8045(3) -0.0022(4) 0.6900(3) 0.0424(10) Uani 1 1 d . . . C11 C 0.7401(4) -0.0817(4) 0.6193(3) 0.0518(12) Uani 1 1 d . . . H11 H 0.6659 -0.0884 0.5986 0.062 Uiso 1 1 calc R . . C12 C 0.7824(4) -0.1478(4) 0.5810(3) 0.0442(11) Uani 1 1 d . . . H12 H 0.7378 -0.1990 0.5346 0.053 Uiso 1 1 calc R . . C13 C 0.8928(4) -0.1391(4) 0.6110(3) 0.0425(10) Uani 1 1 d . . . C14 C 0.9596(4) -0.0634(4) 0.6801(3) 0.0493(11) Uani 1 1 d . . . H14 H 1.0338 -0.0586 0.7002 0.059 Uiso 1 1 calc R . . C15 C 0.9160(3) 0.0061(4) 0.7201(3) 0.0427(10) Uani 1 1 d . . . H15 H 0.9608 0.0574 0.7663 0.051 Uiso 1 1 calc R . . C16 C 0.6586(4) 0.2918(4) 0.5490(3) 0.0429(10) Uani 1 1 d . . . C17 C 0.7257(4) 0.2228(4) 0.5333(3) 0.0447(11) Uani 1 1 d . . . H17 H 0.7135 0.1457 0.5268 0.054 Uiso 1 1 calc R . . C18 C 0.8114(4) 0.2692(4) 0.5274(3) 0.0409(10) Uani 1 1 d . . . H18 H 0.8566 0.2232 0.5170 0.049 Uiso 1 1 calc R . . C19 C 0.8290(4) 0.3846(4) 0.5370(3) 0.0494(11) Uani 1 1 d . . . C20 C 0.7624(4) 0.4533(4) 0.5531(3) 0.0474(11) Uani 1 1 d . . . H20 H 0.7748 0.5304 0.5598 0.057 Uiso 1 1 calc R . . C21 C 0.6767(4) 0.4070(4) 0.5593(3) 0.0441(10) Uani 1 1 d . . . H21 H 0.6319 0.4529 0.5701 0.053 Uiso 1 1 calc R . . C22 C 0.1399(4) 0.1716(4) 0.7227(3) 0.0494(12) Uani 1 1 d . . . H22A H 0.1710 0.1424 0.7847 0.074 Uiso 1 1 calc R . . H22B H 0.0614 0.1760 0.6929 0.074 Uiso 1 1 calc R . . H22C H 0.1690 0.2452 0.7257 0.074 Uiso 1 1 calc R . . C23 C 0.9399(4) -0.2125(4) 0.5645(3) 0.0483(11) Uani 1 1 d . . . H23A H 0.9836 -0.1668 0.5492 0.072 Uiso 1 1 calc R . . H23B H 0.8805 -0.2456 0.5086 0.072 Uiso 1 1 calc R . . H23C H 0.9848 -0.2708 0.6069 0.072 Uiso 1 1 calc R . . C24 C 0.9202(4) 0.4365(4) 0.5283(3) 0.0493(12) Uani 1 1 d . . . H24A H 0.9900 0.4191 0.5830 0.074 Uiso 1 1 calc R . . H24B H 0.9107 0.5164 0.5223 0.074 Uiso 1 1 calc R . . H24C H 0.9175 0.4067 0.4741 0.074 Uiso 1 1 calc R . . C25 C 0.6348(4) 0.2906(4) 0.7300(3) 0.0446(11) Uani 1 1 d . . . H25A H 0.6335 0.2684 0.7842 0.067 Uiso 1 1 calc R . . H25B H 0.5867 0.3537 0.7010 0.067 Uiso 1 1 calc R . . H25C H 0.7083 0.3113 0.7481 0.067 Uiso 1 1 calc R . . N1 N 0.5975(3) 0.1960(3) 0.6631(3) 0.0437(9) Uani 1 1 d . . . O1 O 0.1684(3) 0.0958(3) 0.6677(2) 0.0465(7) Uani 1 1 d . . . O2 O 0.8228(3) 0.1296(3) 0.8026(2) 0.0521(8) Uani 1 1 d . . . O3 O 0.5228(2) 0.1277(3) 0.5035(2) 0.0498(8) Uani 1 1 d . . . O4 O 0.4701(3) 0.3151(3) 0.5293(2) 0.0493(8) Uani 1 1 d . . . S2 S 0.55108(9) 0.22983(10) 0.55495(8) 0.0454(3) 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 0.0405(2) 0.0467(3) 0.0461(3) 0.0203(2) 0.01673(19) 0.0135(2) C1 0.051(3) 0.047(3) 0.045(2) -0.005(2) 0.027(2) -0.007(2) C2 0.048(2) 0.042(3) 0.040(2) 0.0030(19) 0.0301(19) -0.0036(19) C3 0.045(2) 0.038(2) 0.043(2) 0.0014(19) 0.022(2) -0.0011(19) C4 0.037(2) 0.050(3) 0.040(2) -0.003(2) 0.0124(19) 0.001(2) C5 0.056(3) 0.044(3) 0.044(3) -0.006(2) 0.031(2) -0.009(2) C6 0.046(2) 0.031(2) 0.040(2) -0.0004(18) 0.0258(19) -0.0069(18) C7 0.050(3) 0.030(2) 0.050(3) 0.0005(19) 0.020(2) -0.0016(19) C8 0.049(3) 0.028(2) 0.048(3) -0.0025(19) 0.012(2) -0.0055(19) C9 0.038(2) 0.042(3) 0.045(3) -0.006(2) 0.013(2) -0.0060(19) C10 0.033(2) 0.046(3) 0.048(3) 0.006(2) 0.0212(19) -0.0010(18) C11 0.039(2) 0.053(3) 0.055(3) -0.007(2) 0.019(2) -0.005(2) C12 0.042(2) 0.034(2) 0.042(2) -0.0045(19) 0.0123(19) 0.0072(18) C13 0.046(2) 0.038(2) 0.047(3) 0.0134(19) 0.027(2) 0.0110(19) C14 0.045(2) 0.052(3) 0.047(3) -0.011(2) 0.022(2) 0.004(2) C15 0.040(2) 0.047(3) 0.040(2) -0.014(2) 0.0201(19) -0.0102(19) C16 0.053(3) 0.040(2) 0.039(2) -0.0022(19) 0.027(2) -0.011(2) C17 0.046(2) 0.044(3) 0.046(3) 0.001(2) 0.025(2) -0.009(2) C18 0.047(2) 0.038(2) 0.044(2) -0.0056(19) 0.028(2) -0.0094(19) C19 0.045(2) 0.050(3) 0.051(3) -0.018(2) 0.024(2) -0.018(2) C20 0.045(2) 0.038(2) 0.047(3) -0.012(2) 0.015(2) -0.016(2) C21 0.046(2) 0.050(3) 0.041(2) -0.013(2) 0.027(2) -0.013(2) C22 0.043(3) 0.052(3) 0.045(3) -0.012(2) 0.017(2) 0.007(2) C23 0.051(3) 0.047(3) 0.037(2) 0.010(2) 0.016(2) 0.016(2) C24 0.049(3) 0.044(3) 0.047(3) -0.010(2) 0.020(2) -0.019(2) C25 0.045(2) 0.036(2) 0.044(2) -0.010(2) 0.018(2) -0.0069(19) N1 0.0382(19) 0.0328(19) 0.048(2) -0.0044(16) 0.0146(16) -0.0062(15) O1 0.0507(18) 0.0393(17) 0.0486(18) -0.0099(14) 0.0254(15) -0.0033(14) O2 0.0500(18) 0.050(2) 0.0417(17) -0.0147(15) 0.0137(14) -0.0176(15) O3 0.0400(16) 0.053(2) 0.0494(18) -0.0107(15) 0.0186(14) -0.0143(14) O4 0.0479(17) 0.0426(18) 0.0431(18) 0.0107(14) 0.0139(14) 0.0059(14) S2 0.0395(6) 0.0432(6) 0.0494(6) 0.0033(5) 0.0206(5) -0.0073(5) _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 C7 1.978(4) . ? C1 C2 1.388(6) . ? C1 C6 1.395(6) . ? C1 H1 0.9300 . ? C2 C3 1.392(6) . ? C2 H2 0.9300 . ? C3 O1 1.372(5) . ? C3 C4 1.380(7) . ? C4 C5 1.393(6) . ? C4 H4 0.9300 . ? C5 C6 1.387(6) . ? C5 H5 0.9300 . ? C6 C7 1.503(6) . ? C7 C8 1.509(7) . ? C7 H7 0.9800 . ? C8 N1 1.426(5) . ? C8 C9 1.569(6) . ? C8 H8 0.9800 . ? C9 O2 1.219(5) . ? C9 C10 1.495(7) . ? C10 C15 1.399(6) . ? C10 C11 1.418(6) . ? C11 C12 1.345(7) . ? C11 H11 0.9300 . ? C12 C13 1.385(6) . ? C12 H12 0.9300 . ? C13 C14 1.383(6) . ? C13 C23 1.543(6) . ? C14 C15 1.402(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.389(7) . ? C16 C21 1.390(6) . ? C16 S2 1.753(5) . ? C17 C18 1.394(6) . ? C17 H17 0.9300 . ? C18 C19 1.392(6) . ? C18 H18 0.9300 . ? C19 C20 1.385(7) . ? C19 C24 1.517(6) . ? C20 C21 1.395(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 O1 1.494(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N1 1.481(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? N1 S2 1.626(4) . ? O3 S2 1.423(3) . ? O4 S2 1.426(3) . ? 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 C2 C1 C6 120.1(4) . . ? C2 C1 H1 120.0 . . ? C6 C1 H1 120.0 . . ? C1 C2 C3 119.7(4) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? O1 C3 C4 115.5(4) . . ? O1 C3 C2 124.3(4) . . ? C4 C3 C2 120.2(4) . . ? C3 C4 C5 120.5(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 119.5(4) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 120.1(4) . . ? C5 C6 C7 121.8(4) . . ? C1 C6 C7 118.1(4) . . ? C6 C7 C8 114.2(4) . . ? C6 C7 Br1 109.9(3) . . ? C8 C7 Br1 108.3(3) . . ? C6 C7 H7 108.1 . . ? C8 C7 H7 108.1 . . ? Br1 C7 H7 108.1 . . ? N1 C8 C7 113.3(4) . . ? N1 C8 C9 111.9(4) . . ? C7 C8 C9 109.8(4) . . ? N1 C8 H8 107.2 . . ? C7 C8 H8 107.2 . . ? C9 C8 H8 107.2 . . ? O2 C9 C10 121.0(4) . . ? O2 C9 C8 115.4(4) . . ? C10 C9 C8 123.4(4) . . ? C15 C10 C11 117.7(4) . . ? C15 C10 C9 118.2(4) . . ? C11 C10 C9 124.1(4) . . ? C12 C11 C10 122.4(4) . . ? C12 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? C11 C12 C13 119.6(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.4(4) . . ? C14 C13 C23 120.3(4) . . ? C12 C13 C23 119.3(4) . . ? C13 C14 C15 120.3(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C10 C15 C14 119.5(4) . . ? C10 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C17 C16 C21 120.3(4) . . ? C17 C16 S2 118.3(3) . . ? C21 C16 S2 121.3(4) . . ? C16 C17 C18 119.9(4) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 119.6(4) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C20 C19 C18 120.4(4) . . ? C20 C19 C24 119.4(4) . . ? C18 C19 C24 120.2(4) . . ? C19 C20 C21 120.0(4) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C16 C21 C20 119.7(4) . . ? C16 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? O1 C22 H22A 109.5 . . ? O1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C13 C23 H23A 109.5 . . ? C13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N1 C25 H25A 109.5 . . ? N1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C8 N1 C25 118.8(4) . . ? C8 N1 S2 122.2(3) . . ? C25 N1 S2 115.7(3) . . ? C3 O1 C22 116.7(3) . . ? O3 S2 O4 119.91(19) . . ? O3 S2 N1 106.7(2) . . ? O4 S2 N1 107.8(2) . . ? O3 S2 C16 107.6(2) . . ? O4 S2 C16 106.2(2) . . ? N1 S2 C16 108.2(2) . . ? 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 C6 C1 C2 C3 0.7(7) . . . . ? C1 C2 C3 O1 -178.9(4) . . . . ? C1 C2 C3 C4 -0.7(7) . . . . ? O1 C3 C4 C5 179.1(4) . . . . ? C2 C3 C4 C5 0.7(7) . . . . ? C3 C4 C5 C6 -0.7(7) . . . . ? C4 C5 C6 C1 0.7(7) . . . . ? C4 C5 C6 C7 179.7(4) . . . . ? C2 C1 C6 C5 -0.7(7) . . . . ? C2 C1 C6 C7 -179.8(4) . . . . ? C5 C6 C7 C8 47.2(6) . . . . ? C1 C6 C7 C8 -133.8(4) . . . . ? C5 C6 C7 Br1 -74.7(5) . . . . ? C1 C6 C7 Br1 104.3(4) . . . . ? C6 C7 C8 N1 53.2(5) . . . . ? Br1 C7 C8 N1 175.9(3) . . . . ? C6 C7 C8 C9 179.1(4) . . . . ? Br1 C7 C8 C9 -58.1(4) . . . . ? N1 C8 C9 O2 63.9(6) . . . . ? C7 C8 C9 O2 -62.8(5) . . . . ? N1 C8 C9 C10 -112.4(5) . . . . ? C7 C8 C9 C10 120.8(5) . . . . ? O2 C9 C10 C15 -6.6(7) . . . . ? C8 C9 C10 C15 169.5(4) . . . . ? O2 C9 C10 C11 172.2(5) . . . . ? C8 C9 C10 C11 -11.7(7) . . . . ? C15 C10 C11 C12 -0.1(7) . . . . ? C9 C10 C11 C12 -179.0(5) . . . . ? C10 C11 C12 C13 0.1(7) . . . . ? C11 C12 C13 C14 0.2(7) . . . . ? C11 C12 C13 C23 -178.1(4) . . . . ? C12 C13 C14 C15 -0.5(7) . . . . ? C23 C13 C14 C15 177.7(4) . . . . ? C11 C10 C15 C14 -0.2(7) . . . . ? C9 C10 C15 C14 178.7(4) . . . . ? C13 C14 C15 C10 0.5(7) . . . . ? C21 C16 C17 C18 -0.3(7) . . . . ? S2 C16 C17 C18 179.4(3) . . . . ? C16 C17 C18 C19 -0.1(7) . . . . ? C17 C18 C19 C20 0.4(7) . . . . ? C17 C18 C19 C24 -178.5(4) . . . . ? C18 C19 C20 C21 -0.3(7) . . . . ? C24 C19 C20 C21 178.6(4) . . . . ? C17 C16 C21 C20 0.4(7) . . . . ? S2 C16 C21 C20 -179.3(3) . . . . ? C19 C20 C21 C16 -0.1(7) . . . . ? C7 C8 N1 C25 55.2(5) . . . . ? C9 C8 N1 C25 -69.7(5) . . . . ? C7 C8 N1 S2 -146.1(3) . . . . ? C9 C8 N1 S2 89.0(4) . . . . ? C4 C3 O1 C22 -166.2(4) . . . . ? C2 C3 O1 C22 12.1(6) . . . . ? C8 N1 S2 O3 19.2(4) . . . . ? C25 N1 S2 O3 178.5(3) . . . . ? C8 N1 S2 O4 149.2(3) . . . . ? C25 N1 S2 O4 -51.5(4) . . . . ? C8 N1 S2 C16 -96.4(4) . . . . ? C25 N1 S2 C16 62.9(4) . . . . ? C17 C16 S2 O3 -24.9(4) . . . . ? C21 C16 S2 O3 154.8(4) . . . . ? C17 C16 S2 O4 -154.5(4) . . . . ? C21 C16 S2 O4 25.2(4) . . . . ? C17 C16 S2 N1 90.0(4) . . . . ? C21 C16 S2 N1 -90.3(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.539 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.078 # Attachment '- 2ab.cif' data_sh1 _database_code_depnum_ccdc_archive 'CCDC 772859' #TrackingRef '- 2ab.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H22 Br N O4 S' _chemical_formula_sum 'C24 H22 Br N O4 S' _chemical_formula_weight 500.40 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 10.5553(14) _cell_length_b 8.6908(12) _cell_length_c 26.008(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.346(4) _cell_angle_gamma 90.00 _cell_volume 2251.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3166 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 22.86 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 1.950 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6113 _exptl_absorpt_correction_T_max 0.6965 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11831 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4415 _reflns_number_gt 3681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _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^)+(0.06P)^2^+1.99P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4415 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 Br1 Br 0.94240(3) 0.51737(4) 0.902490(16) 0.04246(14) Uani 1 1 d . . . S1 S 1.21305(9) 0.17037(12) 0.93354(4) 0.0419(2) Uani 1 1 d . . . O1 O 1.2065(3) 0.1474(3) 0.87855(11) 0.0454(7) Uani 1 1 d . . . O2 O 1.2892(3) 0.2962(3) 0.96447(11) 0.0456(6) Uani 1 1 d . . . O3 O 0.9241(2) -0.0659(3) 0.87539(11) 0.0432(6) Uani 1 1 d . . . O4 O 0.4692(3) 0.3643(3) 0.66295(11) 0.0479(7) Uani 1 1 d . . . N1 N 1.0577(3) 0.1879(4) 0.93088(12) 0.0373(7) Uani 1 1 d . . . C1 C 1.4264(4) -0.4068(5) 1.06341(16) 0.0429(9) Uani 1 1 d . . . H1A H 1.4844 -0.4585 1.0473 0.064 Uiso 1 1 calc R . . H1B H 1.3535 -0.4736 1.0628 0.064 Uiso 1 1 calc R . . H1C H 1.4762 -0.3798 1.1004 0.064 Uiso 1 1 calc R . . C2 C 1.3712(4) -0.2622(4) 1.03133(16) 0.0400(8) Uani 1 1 d . . . C3 C 1.4090(4) -0.1185(4) 1.05375(15) 0.0401(8) Uani 1 1 d . . . H3 H 1.4685 -0.1120 1.0892 0.048 Uiso 1 1 calc R . . C4 C 1.3612(4) 0.0186(5) 1.02506(16) 0.0424(9) Uani 1 1 d . . . H4 H 1.3864 0.1149 1.0407 0.051 Uiso 1 1 calc R . . C5 C 1.2735(4) 0.0017(4) 0.97161(15) 0.0395(8) Uani 1 1 d . . . C6 C 1.2364(4) -0.1402(5) 0.94790(16) 0.0429(9) Uani 1 1 d . . . H6 H 1.1789 -0.1466 0.9121 0.051 Uiso 1 1 calc R . . C7 C 1.2845(4) -0.2738(5) 0.97717(15) 0.0422(9) Uani 1 1 d . . . H7 H 1.2596 -0.3697 0.9612 0.051 Uiso 1 1 calc R . . C8 C 1.0279(4) 0.2105(5) 0.98237(16) 0.0448(9) Uani 1 1 d . . . H8A H 1.0643 0.3072 0.9984 0.067 Uiso 1 1 calc R . . H8B H 1.0676 0.1286 1.0073 0.067 Uiso 1 1 calc R . . H8C H 0.9324 0.2103 0.9747 0.067 Uiso 1 1 calc R . . C9 C 0.9547(4) 0.2009(5) 0.87974(15) 0.0398(8) Uani 1 1 d . . . C10 C 0.8874(4) 0.3302(5) 0.86297(16) 0.0423(9) Uani 1 1 d . . . C11 C 0.9218(4) 0.0519(5) 0.84906(15) 0.0410(8) Uani 1 1 d . . . C12 C 0.8878(4) 0.0464(4) 0.78900(16) 0.0415(9) Uani 1 1 d . . . C13 C 0.8026(4) -0.0729(5) 0.76076(17) 0.0452(9) Uani 1 1 d . . . H13 H 0.7712 -0.1459 0.7797 0.054 Uiso 1 1 calc R . . C14 C 0.7656(4) -0.0807(5) 0.70399(15) 0.0416(9) Uani 1 1 d . . . H14 H 0.7085 -0.1581 0.6849 0.050 Uiso 1 1 calc R . . C15 C 0.8140(4) 0.0263(5) 0.67691(18) 0.0491(10) Uani 1 1 d . . . H15 H 0.7886 0.0213 0.6391 0.059 Uiso 1 1 calc R . . C16 C 0.9005(4) 0.1426(5) 0.70447(17) 0.0459(9) Uani 1 1 d . . . H16 H 0.9338 0.2130 0.6852 0.055 Uiso 1 1 calc R . . C17 C 0.9376(4) 0.1533(5) 0.76154(17) 0.0444(9) Uani 1 1 d . . . H17 H 0.9946 0.2312 0.7804 0.053 Uiso 1 1 calc R . . C18 C 0.7671(4) 0.3489(5) 0.81322(17) 0.0459(9) Uani 1 1 d . . . C19 C 0.7690(4) 0.4570(5) 0.77391(16) 0.0407(8) Uani 1 1 d . . . H19 H 0.8387 0.5280 0.7812 0.049 Uiso 1 1 calc R . . C20 C 0.6675(4) 0.4587(5) 0.72428(16) 0.0442(9) Uani 1 1 d . . . H20 H 0.6693 0.5303 0.6979 0.053 Uiso 1 1 calc R . . C21 C 0.5630(4) 0.3544(5) 0.71352(19) 0.0529(10) Uani 1 1 d . . . C22 C 0.5567(4) 0.2507(5) 0.75275(17) 0.0497(10) Uani 1 1 d . . . H22 H 0.4850 0.1826 0.7457 0.060 Uiso 1 1 calc R . . C23 C 0.6601(4) 0.2492(5) 0.80356(18) 0.0478(9) Uani 1 1 d . . . H23 H 0.6563 0.1810 0.8306 0.057 Uiso 1 1 calc R . . C24 C 0.3794(4) 0.2378(5) 0.64440(17) 0.0471(9) Uani 1 1 d . . . H24A H 0.4301 0.1445 0.6474 0.071 Uiso 1 1 calc R . . H24B H 0.3256 0.2539 0.6070 0.071 Uiso 1 1 calc R . . H24C H 0.3221 0.2298 0.6663 0.071 Uiso 1 1 calc R . . 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 0.0331(2) 0.0418(2) 0.0434(2) -0.01418(16) 0.00044(15) 0.00734(14) S1 0.0317(4) 0.0479(5) 0.0383(5) 0.0056(4) 0.0014(4) 0.0014(4) O1 0.0527(16) 0.0472(16) 0.0417(15) 0.0133(12) 0.0230(13) 0.0166(12) O2 0.0386(13) 0.0424(15) 0.0475(15) 0.0077(12) 0.0030(11) -0.0066(11) O3 0.0310(12) 0.0483(16) 0.0429(15) 0.0059(13) 0.0024(11) -0.0040(11) O4 0.0446(15) 0.0455(15) 0.0462(16) 0.0132(12) 0.0049(12) -0.0111(12) N1 0.0342(15) 0.0408(16) 0.0329(15) -0.0091(13) 0.0058(12) 0.0076(13) C1 0.0334(18) 0.046(2) 0.041(2) 0.0145(17) 0.0016(16) 0.0030(15) C2 0.0368(18) 0.040(2) 0.043(2) 0.0107(16) 0.0136(16) 0.0043(15) C3 0.0372(19) 0.043(2) 0.0332(19) 0.0032(16) 0.0023(15) 0.0041(15) C4 0.0336(18) 0.041(2) 0.043(2) -0.0064(17) 0.0003(15) 0.0024(15) C5 0.0320(17) 0.045(2) 0.0354(19) 0.0068(16) 0.0035(14) 0.0034(15) C6 0.0391(19) 0.045(2) 0.0355(19) -0.0092(16) 0.0000(15) 0.0042(16) C7 0.0360(18) 0.044(2) 0.039(2) -0.0014(16) 0.0023(16) -0.0008(15) C8 0.052(2) 0.049(2) 0.042(2) -0.0133(17) 0.0272(18) 0.0043(18) C9 0.0400(19) 0.042(2) 0.0384(19) -0.0086(16) 0.0137(16) -0.0018(16) C10 0.044(2) 0.041(2) 0.041(2) -0.0151(17) 0.0127(16) -0.0014(16) C11 0.0402(19) 0.043(2) 0.0355(19) 0.0015(16) 0.0067(16) 0.0050(16) C12 0.0372(19) 0.0391(19) 0.047(2) -0.0044(17) 0.0123(16) 0.0126(15) C13 0.0345(19) 0.045(2) 0.048(2) -0.0131(18) 0.0023(17) 0.0062(16) C14 0.0375(19) 0.049(2) 0.0366(19) -0.0132(17) 0.0093(16) 0.0080(16) C15 0.045(2) 0.053(2) 0.048(2) -0.0153(19) 0.0136(18) 0.0127(18) C16 0.039(2) 0.048(2) 0.048(2) -0.0031(18) 0.0113(17) 0.0162(16) C17 0.039(2) 0.050(2) 0.046(2) -0.0023(18) 0.0160(17) 0.0095(16) C18 0.043(2) 0.041(2) 0.052(2) -0.0046(18) 0.0136(18) 0.0049(16) C19 0.0296(17) 0.041(2) 0.044(2) 0.0028(16) 0.0031(15) 0.0064(15) C20 0.041(2) 0.047(2) 0.043(2) 0.0036(17) 0.0107(16) 0.0004(16) C21 0.048(2) 0.054(3) 0.054(3) 0.002(2) 0.014(2) 0.0035(19) C22 0.041(2) 0.055(2) 0.048(2) 0.0046(19) 0.0079(17) 0.0011(17) C23 0.040(2) 0.054(2) 0.050(2) -0.0024(19) 0.0164(18) 0.0009(17) C24 0.044(2) 0.048(2) 0.045(2) -0.0153(18) 0.0080(17) -0.0152(17) _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 1.909(4) . ? S1 O1 1.423(3) . ? S1 O2 1.435(3) . ? S1 N1 1.625(3) . ? S1 C5 1.765(4) . ? O3 C11 1.227(5) . ? O4 C21 1.362(5) . ? O4 C24 1.427(5) . ? N1 C9 1.416(5) . ? N1 C8 1.487(5) . ? C1 C2 1.514(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.380(6) . ? C2 C7 1.406(5) . ? C3 C4 1.408(5) . ? C3 H3 0.9300 . ? C4 C5 1.399(5) . ? C4 H4 0.9300 . ? C5 C6 1.376(5) . ? C6 C7 1.389(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.324(6) . ? C9 C11 1.501(5) . ? C10 C18 1.492(6) . ? C11 C12 1.483(5) . ? C12 C17 1.378(6) . ? C12 C13 1.409(6) . ? C13 C14 1.398(6) . ? C13 H13 0.9300 . ? C14 C15 1.364(6) . ? C14 H14 0.9300 . ? C15 C16 1.391(6) . ? C15 H15 0.9300 . ? C16 C17 1.407(6) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C23 1.378(6) . ? C18 C19 1.393(6) . ? C19 C20 1.377(5) . ? C19 H19 0.9300 . ? C20 C21 1.383(6) . ? C20 H20 0.9300 . ? C21 C22 1.379(6) . ? C22 C23 1.408(6) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 O1 S1 O2 120.14(19) . . ? O1 S1 N1 104.93(16) . . ? O2 S1 N1 108.82(17) . . ? O1 S1 C5 109.59(18) . . ? O2 S1 C5 106.66(17) . . ? N1 S1 C5 105.89(18) . . ? C21 O4 C24 117.8(3) . . ? C9 N1 C8 120.6(3) . . ? C9 N1 S1 119.8(3) . . ? C8 N1 S1 119.1(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C7 119.3(3) . . ? C3 C2 C1 120.9(3) . . ? C7 C2 C1 119.8(4) . . ? C2 C3 C4 122.6(3) . . ? C2 C3 H3 118.7 . . ? C4 C3 H3 118.7 . . ? C5 C4 C3 116.1(3) . . ? C5 C4 H4 121.9 . . ? C3 C4 H4 121.9 . . ? C6 C5 C4 122.4(3) . . ? C6 C5 S1 119.8(3) . . ? C4 C5 S1 117.9(3) . . ? C5 C6 C7 120.4(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 119.2(4) . . ? C6 C7 H7 120.4 . . ? C2 C7 H7 120.4 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N1 122.6(3) . . ? C10 C9 C11 123.6(3) . . ? N1 C9 C11 113.6(3) . . ? C9 C10 C18 126.0(3) . . ? C9 C10 Br1 120.8(3) . . ? C18 C10 Br1 113.2(3) . . ? O3 C11 C12 120.9(4) . . ? O3 C11 C9 117.7(3) . . ? C12 C11 C9 121.4(3) . . ? C17 C12 C13 120.9(4) . . ? C17 C12 C11 121.5(4) . . ? C13 C12 C11 117.6(4) . . ? C14 C13 C12 119.5(4) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 119.4(4) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 121.6(4) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C15 C16 C17 119.8(4) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C12 C17 C16 118.8(4) . . ? C12 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C23 C18 C19 120.0(4) . . ? C23 C18 C10 120.0(4) . . ? C19 C18 C10 119.7(4) . . ? C20 C19 C18 119.9(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.2(4) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? O4 C21 C22 123.9(4) . . ? O4 C21 C20 115.5(4) . . ? C22 C21 C20 120.6(4) . . ? C21 C22 C23 119.2(4) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C18 C23 C22 119.9(4) . . ? C18 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? O4 C24 H24A 109.5 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 O1 S1 N1 C9 -9.2(3) . . . . ? O2 S1 N1 C9 120.6(3) . . . . ? C5 S1 N1 C9 -125.1(3) . . . . ? O1 S1 N1 C8 178.8(3) . . . . ? O2 S1 N1 C8 -51.4(3) . . . . ? C5 S1 N1 C8 62.9(3) . . . . ? C7 C2 C3 C4 1.9(6) . . . . ? C1 C2 C3 C4 179.3(4) . . . . ? C2 C3 C4 C5 -0.9(6) . . . . ? C3 C4 C5 C6 -0.5(6) . . . . ? C3 C4 C5 S1 -178.9(3) . . . . ? O1 S1 C5 C6 -36.8(4) . . . . ? O2 S1 C5 C6 -168.4(3) . . . . ? N1 S1 C5 C6 75.8(4) . . . . ? O1 S1 C5 C4 141.6(3) . . . . ? O2 S1 C5 C4 10.1(4) . . . . ? N1 S1 C5 C4 -105.7(3) . . . . ? C4 C5 C6 C7 0.9(6) . . . . ? S1 C5 C6 C7 179.3(3) . . . . ? C5 C6 C7 C2 0.1(6) . . . . ? C3 C2 C7 C6 -1.5(6) . . . . ? C1 C2 C7 C6 -178.9(4) . . . . ? C8 N1 C9 C10 61.9(5) . . . . ? S1 N1 C9 C10 -110.0(4) . . . . ? C8 N1 C9 C11 -113.0(4) . . . . ? S1 N1 C9 C11 75.1(4) . . . . ? N1 C9 C10 C18 -172.0(4) . . . . ? C11 C9 C10 C18 2.5(7) . . . . ? N1 C9 C10 Br1 9.1(6) . . . . ? C11 C9 C10 Br1 -176.5(3) . . . . ? C10 C9 C11 O3 -137.5(4) . . . . ? N1 C9 C11 O3 37.5(5) . . . . ? C10 C9 C11 C12 42.6(6) . . . . ? N1 C9 C11 C12 -142.5(4) . . . . ? O3 C11 C12 C17 -151.5(4) . . . . ? C9 C11 C12 C17 28.4(5) . . . . ? O3 C11 C12 C13 28.3(5) . . . . ? C9 C11 C12 C13 -151.8(3) . . . . ? C17 C12 C13 C14 -1.5(5) . . . . ? C11 C12 C13 C14 178.7(3) . . . . ? C12 C13 C14 C15 0.8(5) . . . . ? C13 C14 C15 C16 0.6(6) . . . . ? C14 C15 C16 C17 -1.4(6) . . . . ? C13 C12 C17 C16 0.7(5) . . . . ? C11 C12 C17 C16 -179.5(3) . . . . ? C15 C16 C17 C12 0.7(5) . . . . ? C9 C10 C18 C23 50.0(6) . . . . ? Br1 C10 C18 C23 -130.9(4) . . . . ? C9 C10 C18 C19 -123.3(5) . . . . ? Br1 C10 C18 C19 55.7(4) . . . . ? C23 C18 C19 C20 -3.5(6) . . . . ? C10 C18 C19 C20 169.9(4) . . . . ? C18 C19 C20 C21 0.6(6) . . . . ? C24 O4 C21 C22 -16.8(6) . . . . ? C24 O4 C21 C20 164.3(4) . . . . ? C19 C20 C21 O4 -179.0(4) . . . . ? C19 C20 C21 C22 2.0(7) . . . . ? O4 C21 C22 C23 179.3(4) . . . . ? C20 C21 C22 C23 -1.8(7) . . . . ? C19 C18 C23 C22 3.7(6) . . . . ? C10 C18 C23 C22 -169.7(4) . . . . ? C21 C22 C23 C18 -1.1(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.322 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.077