data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H25 Br O4 S' _chemical_formula_weight 549.46 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' '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 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 11.508(4) _cell_length_b 9.580(4) _cell_length_c 23.335(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.596(6) _cell_angle_gamma 90.00 _cell_volume 2520.3(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5047 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 26.04 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.748 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6998 _exptl_absorpt_correction_T_max 0.7438 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 CCD _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14890 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4448 _reflns_number_gt 3209 _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^)+(0.1075P)^2^+13.9261P] 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 4448 _refine_ls_number_parameters 328 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1951 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 0.825 _refine_ls_restrained_S_all 0.825 _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 Br1 Br -0.19461(6) -0.01096(7) 1.00177(3) 0.0608(3) Uani 1 1 d . . . C1 C -0.1734(4) 0.1776(6) 0.9803(2) 0.0394(12) Uani 1 1 d . . . C2 C -0.2324(5) 0.2825(7) 1.0046(2) 0.0503(14) Uani 1 1 d . . . H2 H -0.2810 0.2606 1.0307 0.060 Uiso 1 1 calc R . . C3 C -0.2176(5) 0.4155(7) 0.9896(2) 0.0489(14) Uani 1 1 d . . . H3 H -0.2576 0.4854 1.0054 0.059 Uiso 1 1 calc R . . C4 C -0.1440(4) 0.4525(6) 0.9512(2) 0.0386(12) Uani 1 1 d . . . C5 C -0.0845(4) 0.3452(5) 0.9260(2) 0.0324(10) Uani 1 1 d . . . C6 C -0.1018(4) 0.2062(5) 0.9419(2) 0.0367(11) Uani 1 1 d . . . H6 H -0.0645 0.1338 0.9261 0.044 Uiso 1 1 calc R . . C7 C -0.0094(4) 0.3805(5) 0.8870(2) 0.0316(10) Uani 1 1 d . . . C8 C 0.0032(4) 0.5182(5) 0.8733(2) 0.0348(11) Uani 1 1 d . . . C9 C -0.0541(5) 0.6252(5) 0.8993(3) 0.0441(13) Uani 1 1 d . . . H9 H -0.0420 0.7182 0.8907 0.053 Uiso 1 1 calc R . . C10 C -0.1261(5) 0.5929(6) 0.9364(2) 0.0441(13) Uani 1 1 d . . . H10 H -0.1644 0.6639 0.9524 0.053 Uiso 1 1 calc R . . C11 C 0.0544(4) 0.2687(5) 0.8602(2) 0.0329(11) Uani 1 1 d . . . H11 H 0.084(4) 0.204(6) 0.892(2) 0.039 Uiso 1 1 d . . . C12 C -0.0232(4) 0.1944(5) 0.8081(2) 0.0358(11) Uani 1 1 d . . . C13 C -0.1201(5) 0.2615(6) 0.7738(3) 0.0472(13) Uani 1 1 d . . . H13 H -0.1369 0.3527 0.7831 0.057 Uiso 1 1 calc R . . C14 C -0.1919(5) 0.1980(8) 0.7269(3) 0.0607(17) Uani 1 1 d . . . H14 H -0.2562 0.2452 0.7048 0.073 Uiso 1 1 calc R . . C15 C -0.1664(6) 0.0626(8) 0.7132(3) 0.0664(19) Uani 1 1 d . . . H15 H -0.2142 0.0177 0.6817 0.080 Uiso 1 1 calc R . . C16 C -0.0730(7) -0.0046(7) 0.7453(3) 0.0662(19) Uani 1 1 d . . . H16 H -0.0577 -0.0958 0.7353 0.079 Uiso 1 1 calc R . . C17 C 0.0026(5) 0.0576(6) 0.7935(3) 0.0478(14) Uani 1 1 d . . . C18 C 0.1078(7) -0.0224(6) 0.8271(3) 0.069(2) Uani 1 1 d . . . H18A H 0.1794 0.0128 0.8173 0.104 Uiso 1 1 calc R . . H18B H 0.0992 -0.1196 0.8172 0.104 Uiso 1 1 calc R . . H18C H 0.1115 -0.0111 0.8684 0.104 Uiso 1 1 calc R . . C19 C 0.1530(4) 0.4743(5) 0.8152(2) 0.0371(11) Uani 1 1 d . . . C20 C 0.1668(4) 0.3323(5) 0.8448(2) 0.0316(10) Uani 1 1 d . . . H20 H 0.191(4) 0.264(6) 0.818(2) 0.038 Uiso 1 1 d . . . C21 C 0.2677(4) 0.3519(5) 0.8973(2) 0.0350(11) Uani 1 1 d . . . C22 C 0.3361(5) 0.4738(5) 0.8850(2) 0.0373(11) Uani 1 1 d . . . C23 C 0.2724(4) 0.5446(5) 0.8365(2) 0.0347(11) Uani 1 1 d . . . C24 C 0.3196(5) 0.6617(6) 0.8156(3) 0.0463(13) Uani 1 1 d . . . H24 H 0.2776 0.7099 0.7834 0.056 Uiso 1 1 calc R . . C25 C 0.4309(6) 0.7055(7) 0.8435(3) 0.0591(16) Uani 1 1 d . . . H25 H 0.4649 0.7828 0.8292 0.071 Uiso 1 1 calc R . . C26 C 0.4926(6) 0.6373(8) 0.8920(3) 0.0651(18) Uani 1 1 d . . . H26 H 0.5664 0.6710 0.9104 0.078 Uiso 1 1 calc R . . C27 C 0.4478(5) 0.5208(6) 0.9138(3) 0.0491(14) Uani 1 1 d . . . H27 H 0.4900 0.4746 0.9465 0.059 Uiso 1 1 calc R . . O1 O 0.0685(3) 0.5647(4) 0.83461(19) 0.0492(10) Uani 1 1 d . . . O2 O 0.1205(4) 0.4601(4) 0.75548(17) 0.0514(10) Uani 1 1 d D . . H1O H 0.118(6) 0.540(3) 0.741(3) 0.062 Uiso 1 1 d D . . O3 O 0.2870(3) 0.2808(4) 0.94052(17) 0.0486(9) Uani 1 1 d . . . S1 S 0.9772(2) 0.6790(2) 0.63870(10) 0.0863(7) Uani 1 1 d . . . O4 O 1.0846(4) 0.6838(5) 0.6841(2) 0.0808(16) Uani 1 1 d . . . C29 C 1.0084(8) 0.5651(10) 0.5857(4) 0.092(3) Uani 1 1 d . . . H29A H 1.0620 0.6092 0.5646 0.138 Uiso 1 1 calc R . . H29B H 0.9361 0.5415 0.5590 0.138 Uiso 1 1 calc R . . H29C H 1.0442 0.4818 0.6042 0.138 Uiso 1 1 calc R . . C28 C 0.8732(7) 0.5832(11) 0.6652(4) 0.089(3) Uani 1 1 d . . . H28A H 0.9064 0.4946 0.6790 0.133 Uiso 1 1 calc R . . H28B H 0.8050 0.5686 0.6345 0.133 Uiso 1 1 calc R . . H28C H 0.8499 0.6328 0.6968 0.133 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 0.0583(4) 0.0564(4) 0.0685(5) 0.0264(3) 0.0148(3) -0.0002(3) C1 0.038(3) 0.040(3) 0.040(3) 0.011(2) 0.007(2) -0.004(2) C2 0.049(3) 0.065(4) 0.042(3) 0.002(3) 0.021(3) 0.003(3) C3 0.049(3) 0.058(4) 0.043(3) -0.013(3) 0.016(3) 0.006(3) C4 0.039(3) 0.037(3) 0.038(3) -0.010(2) 0.004(2) 0.002(2) C5 0.032(2) 0.032(3) 0.031(3) -0.005(2) 0.0033(19) -0.001(2) C6 0.035(3) 0.038(3) 0.037(3) -0.003(2) 0.006(2) 0.001(2) C7 0.032(2) 0.029(3) 0.034(3) -0.004(2) 0.006(2) 0.0022(19) C8 0.030(2) 0.031(3) 0.043(3) 0.000(2) 0.005(2) 0.002(2) C9 0.043(3) 0.027(3) 0.060(4) -0.005(2) 0.003(3) 0.005(2) C10 0.041(3) 0.039(3) 0.051(3) -0.014(2) 0.008(2) 0.008(2) C11 0.037(3) 0.024(2) 0.039(3) 0.002(2) 0.010(2) 0.005(2) C12 0.042(3) 0.026(2) 0.042(3) -0.004(2) 0.014(2) -0.006(2) C13 0.046(3) 0.045(3) 0.051(3) -0.007(3) 0.010(3) -0.002(3) C14 0.044(3) 0.077(5) 0.058(4) -0.008(3) 0.003(3) -0.013(3) C15 0.066(4) 0.076(5) 0.057(4) -0.020(4) 0.012(3) -0.032(4) C16 0.095(5) 0.039(3) 0.070(5) -0.021(3) 0.029(4) -0.020(4) C17 0.063(4) 0.030(3) 0.054(3) -0.005(2) 0.020(3) -0.006(3) C18 0.095(5) 0.033(3) 0.083(5) -0.005(3) 0.023(4) 0.016(3) C19 0.033(2) 0.038(3) 0.042(3) 0.001(2) 0.011(2) 0.001(2) C20 0.033(2) 0.025(2) 0.038(3) -0.002(2) 0.009(2) 0.0015(19) C21 0.037(3) 0.030(3) 0.039(3) -0.003(2) 0.010(2) 0.004(2) C22 0.042(3) 0.035(3) 0.037(3) -0.002(2) 0.012(2) -0.001(2) C23 0.039(3) 0.032(3) 0.036(3) 0.000(2) 0.013(2) 0.000(2) C24 0.051(3) 0.040(3) 0.052(3) 0.002(3) 0.018(3) -0.005(2) C25 0.058(4) 0.051(4) 0.071(4) 0.005(3) 0.020(3) -0.016(3) C26 0.047(3) 0.071(5) 0.077(5) -0.009(4) 0.009(3) -0.021(3) C27 0.040(3) 0.057(4) 0.049(3) -0.005(3) 0.005(2) 0.000(3) O1 0.050(2) 0.0286(19) 0.076(3) 0.0152(19) 0.030(2) 0.0108(17) O2 0.066(3) 0.045(2) 0.039(2) 0.0058(18) -0.0012(19) -0.009(2) O3 0.054(2) 0.045(2) 0.045(2) 0.0114(18) 0.0050(18) 0.0036(18) S1 0.0954(15) 0.0770(14) 0.0803(14) 0.0186(11) 0.0025(11) -0.0026(11) O4 0.079(3) 0.074(3) 0.079(3) 0.028(3) -0.010(3) -0.020(3) C29 0.088(6) 0.108(7) 0.084(6) -0.021(5) 0.027(5) -0.043(5) C28 0.061(4) 0.117(7) 0.089(6) 0.007(5) 0.016(4) 0.014(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 C1 1.903(5) . ? C1 C6 1.363(7) . ? C1 C2 1.394(8) . ? C2 C3 1.341(9) . ? C3 C4 1.398(8) . ? C4 C10 1.414(8) . ? C4 C5 1.425(7) . ? C5 C6 1.408(7) . ? C5 C7 1.417(7) . ? C7 C8 1.372(7) . ? C7 C11 1.504(6) . ? C8 O1 1.361(6) . ? C8 C9 1.419(7) . ? C9 C10 1.349(8) . ? C11 C12 1.531(7) . ? C11 C20 1.536(7) . ? C12 C13 1.392(8) . ? C12 C17 1.401(7) . ? C13 C14 1.374(8) . ? C14 C15 1.381(10) . ? C15 C16 1.345(11) . ? C16 C17 1.408(9) . ? C17 C18 1.512(9) . ? C19 O2 1.375(7) . ? C19 O1 1.442(6) . ? C19 C20 1.519(7) . ? C19 C23 1.522(7) . ? C20 C21 1.521(7) . ? C21 O3 1.200(6) . ? C21 C22 1.469(7) . ? C22 C23 1.394(7) . ? C22 C27 1.400(8) . ? C23 C24 1.378(7) . ? C24 C25 1.380(8) . ? C25 C26 1.374(10) . ? C26 C27 1.370(9) . ? S1 O4 1.458(5) . ? S1 C28 1.719(9) . ? S1 C29 1.740(9) . ? 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 C6 C1 C2 122.0(5) . . ? C6 C1 Br1 119.4(4) . . ? C2 C1 Br1 118.6(4) . . ? C3 C2 C1 118.8(5) . . ? C2 C3 C4 122.2(5) . . ? C3 C4 C10 122.4(5) . . ? C3 C4 C5 119.0(5) . . ? C10 C4 C5 118.7(5) . . ? C4 C5 C6 118.0(5) . . ? C4 C5 C7 119.9(5) . . ? C6 C5 C7 122.1(4) . . ? C1 C6 C5 120.0(5) . . ? C8 C7 C5 119.0(4) . . ? C8 C7 C11 120.3(4) . . ? C5 C7 C11 120.7(4) . . ? O1 C8 C7 124.6(4) . . ? O1 C8 C9 114.3(4) . . ? C7 C8 C9 121.0(5) . . ? C10 C9 C8 120.4(5) . . ? C9 C10 C4 120.9(5) . . ? C7 C11 C12 114.0(4) . . ? C7 C11 C20 108.6(4) . . ? C12 C11 C20 112.5(4) . . ? C13 C12 C17 118.5(5) . . ? C13 C12 C11 120.9(4) . . ? C17 C12 C11 120.7(5) . . ? C14 C13 C12 122.5(6) . . ? C15 C14 C13 118.6(6) . . ? C16 C15 C14 120.2(6) . . ? C15 C16 C17 122.6(6) . . ? C12 C17 C16 117.6(6) . . ? C12 C17 C18 122.3(5) . . ? C16 C17 C18 120.1(6) . . ? O2 C19 O1 108.3(4) . . ? O2 C19 C20 110.8(4) . . ? O1 C19 C20 114.2(4) . . ? O2 C19 C23 114.8(4) . . ? O1 C19 C23 104.7(4) . . ? C20 C19 C23 104.1(4) . . ? C19 C20 C21 104.4(4) . . ? C19 C20 C11 116.5(4) . . ? C21 C20 C11 113.8(4) . . ? O3 C21 C22 126.9(5) . . ? O3 C21 C20 126.1(5) . . ? C22 C21 C20 107.0(4) . . ? C23 C22 C27 121.0(5) . . ? C23 C22 C21 109.3(4) . . ? C27 C22 C21 129.6(5) . . ? C22 C23 C24 120.2(5) . . ? C22 C23 C19 110.0(4) . . ? C24 C23 C19 129.7(5) . . ? C25 C24 C23 118.3(6) . . ? C26 C25 C24 121.4(6) . . ? C25 C26 C27 121.5(6) . . ? C26 C27 C22 117.4(6) . . ? C8 O1 C19 120.5(4) . . ? O4 S1 C28 107.8(4) . . ? O4 S1 C29 105.7(4) . . ? C28 S1 C29 100.3(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.779 _refine_diff_density_min -0.959 _refine_diff_density_rms 0.094