data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H21 Br N2 O6 S' _chemical_formula_weight 545.40 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' '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 monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3854(8) _cell_length_b 5.7613(6) _cell_length_c 26.815(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.526(5) _cell_angle_gamma 90.00 _cell_volume 1139.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 1.940 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)' _exptl_absorpt_correction_T_min 0.5786 _exptl_absorpt_correction_T_max 0.7456 _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Bruker APEXII' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 23418 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.78 _reflns_number_total 5239 _reflns_number_gt 5090 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0265P)^2^+0.0865P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.021(5) _refine_ls_number_reflns 5239 _refine_ls_number_parameters 308 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0578 _refine_ls_wR_factor_gt 0.0575 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3172(2) 0.8495(3) 0.44603(6) 0.0178(4) Uani 1 1 d . . . C2 C 0.3402(2) 0.6829(3) 0.48306(7) 0.0180(3) Uani 1 1 d . . . H2 H 0.3952 0.5418 0.4764 0.024 Uiso 1 1 calc R . . C3 C 0.2795(2) 0.7303(3) 0.53065(6) 0.0170(4) Uani 1 1 d . . . H3 H 0.2920 0.6194 0.5558 0.023 Uiso 1 1 calc R . . C4 C 0.2003(2) 0.9434(3) 0.54028(6) 0.0150(3) Uani 1 1 d . . . C5 C 0.1808(2) 1.1095(3) 0.50261(7) 0.0184(4) Uani 1 1 d . . . H5 H 0.1291 1.2526 0.5094 0.024 Uiso 1 1 calc R . . C6 C 0.2381(2) 1.0626(3) 0.45518(7) 0.0199(4) Uani 1 1 d . . . H6 H 0.2237 1.1723 0.4299 0.026 Uiso 1 1 calc R . . C7 C 0.1273(2) 1.0000(3) 0.58978(6) 0.0164(3) Uani 1 1 d . . . C8 C 0.0257(3) 0.8357(3) 0.66474(6) 0.0197(4) Uani 1 1 d . . . H8A H -0.0998 0.8828 0.6594 0.026 Uiso 1 1 calc R . . H8B H 0.0887 0.9518 0.6851 0.026 Uiso 1 1 calc R . . C9 C 0.0375(2) 0.6018(3) 0.68941(7) 0.0177(3) Uani 1 1 d . . . H9 H -0.0192 0.4857 0.6670 0.024 Uiso 1 1 calc R . . C10 C 0.2338(2) 0.5310(3) 0.70193(6) 0.0172(3) Uani 1 1 d . . . H10A H 0.2831 0.4422 0.6750 0.023 Uiso 1 1 calc R . . H10B H 0.3096 0.6659 0.7086 0.023 Uiso 1 1 calc R . . C11 C 0.0325(2) 0.3828(3) 0.76642(6) 0.0157(3) Uani 1 1 d . . . H11 H -0.0298 0.2417 0.7546 0.021 Uiso 1 1 calc R . . C12 C -0.0525(2) 0.5938(3) 0.73965(7) 0.0194(4) Uani 1 1 d . . . H12A H -0.1827 0.5750 0.7349 0.026 Uiso 1 1 calc R . . H12B H -0.0278 0.7347 0.7585 0.026 Uiso 1 1 calc R . . C13 C 0.0330(2) 0.3912(3) 0.82276(6) 0.0159(3) Uani 1 1 d . . . C14 C -0.0319(2) 0.2031(3) 0.84891(7) 0.0187(3) Uani 1 1 d . . . H14 H -0.0804 0.0763 0.8315 0.025 Uiso 1 1 calc R . . C15 C -0.0251(3) 0.2021(4) 0.90104(7) 0.0229(4) Uani 1 1 d . . . H15 H -0.0686 0.0749 0.9182 0.031 Uiso 1 1 calc R . . C16 C 0.0463(3) 0.3900(4) 0.92710(7) 0.0231(4) Uani 1 1 d . . . H16 H 0.0527 0.3888 0.9618 0.031 Uiso 1 1 calc R . . C17 C 0.1085(2) 0.5814(3) 0.90117(7) 0.0201(4) Uani 1 1 d . . . H17 H 0.1547 0.7095 0.9186 0.027 Uiso 1 1 calc R . . C18 C 0.1017(2) 0.5814(3) 0.84944(7) 0.0167(3) Uani 1 1 d . . . H18 H 0.1436 0.7098 0.8324 0.022 Uiso 1 1 calc R . . C19 C 0.4621(2) 0.3135(3) 0.82401(6) 0.0147(3) Uani 1 1 d . . . C20 C 0.4409(2) 0.1825(3) 0.86658(7) 0.0166(3) Uani 1 1 d . . . H20 H 0.3823 0.0397 0.8646 0.022 Uiso 1 1 calc R . . C21 C 0.5084(2) 0.2668(4) 0.91233(6) 0.0181(3) Uani 1 1 d . . . H21 H 0.4975 0.1813 0.9415 0.024 Uiso 1 1 calc R . . C22 C 0.5917(2) 0.4805(3) 0.91315(6) 0.0176(4) Uani 1 1 d . . . C23 C 0.6146(2) 0.6141(3) 0.87101(7) 0.0179(3) Uani 1 1 d . . . H23 H 0.6731 0.7570 0.8731 0.024 Uiso 1 1 calc R . . C24 C 0.5475(2) 0.5283(3) 0.82565(7) 0.0167(3) Uani 1 1 d . . . H24 H 0.5595 0.6137 0.7965 0.022 Uiso 1 1 calc R . . N1 N 0.2192(2) 0.3875(3) 0.74710(5) 0.0179(3) Uani 1 1 d . . . N2 N 0.6632(2) 0.5709(3) 0.96170(6) 0.0224(3) Uani 1 1 d . . . O1 O 0.0839(2) 1.1904(2) 0.60280(5) 0.0250(3) Uani 1 1 d . . . O2 O 0.11127(16) 0.8079(3) 0.61744(4) 0.0204(3) Uani 1 1 d . . . O3 O 0.51821(18) 0.2240(2) 0.73145(5) 0.0232(3) Uani 1 1 d . . . O4 O 0.29535(19) -0.0140(2) 0.77539(5) 0.0226(3) Uani 1 1 d . . . O5 O 0.71154(19) 0.7734(3) 0.96353(5) 0.0313(3) Uani 1 1 d . . . O6 O 0.6693(2) 0.4389(3) 0.99748(5) 0.0296(3) Uani 1 1 d . . . S1 S 0.37459(6) 0.20785(7) 0.765593(15) 0.01620(9) Uani 1 1 d . . . Br1 Br 0.39482(2) 0.78254(4) 0.381293(6) 0.02417(6) 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 C1 0.0149(8) 0.0259(9) 0.0128(8) -0.0026(6) 0.0014(6) -0.0044(6) C2 0.0159(8) 0.0162(8) 0.0220(9) -0.0042(7) 0.0022(7) 0.0008(7) C3 0.0179(8) 0.0161(9) 0.0171(7) 0.0013(6) 0.0000(6) 0.0001(6) C4 0.0125(8) 0.0144(8) 0.0179(8) -0.0001(6) -0.0006(6) -0.0010(7) C5 0.0160(8) 0.0175(8) 0.0216(9) 0.0014(7) -0.0013(7) 0.0009(7) C6 0.0195(9) 0.0207(9) 0.0193(9) 0.0053(7) -0.0017(7) -0.0029(7) C7 0.0131(8) 0.0185(8) 0.0174(8) 0.0000(7) -0.0022(6) 0.0018(7) C8 0.0230(9) 0.0221(11) 0.0142(7) 0.0001(6) 0.0022(6) 0.0063(7) C9 0.0181(8) 0.0209(9) 0.0142(8) -0.0015(7) 0.0007(6) 0.0006(7) C10 0.0191(9) 0.0169(8) 0.0158(8) 0.0018(7) 0.0021(6) 0.0012(7) C11 0.0122(8) 0.0195(8) 0.0156(8) -0.0007(7) 0.0034(6) -0.0005(7) C12 0.0171(9) 0.0248(9) 0.0165(8) 0.0017(7) 0.0015(7) 0.0040(7) C13 0.0100(7) 0.0194(8) 0.0185(8) 0.0006(7) 0.0030(6) 0.0024(7) C14 0.0140(8) 0.0173(8) 0.0250(9) 0.0004(7) 0.0050(7) 0.0035(7) C15 0.0193(9) 0.0253(9) 0.0250(9) 0.0103(7) 0.0094(7) 0.0070(7) C16 0.0180(9) 0.0352(10) 0.0163(8) 0.0040(8) 0.0034(7) 0.0089(8) C17 0.0152(8) 0.0241(9) 0.0211(9) -0.0033(7) 0.0004(7) 0.0050(7) C18 0.0135(8) 0.0180(8) 0.0189(8) 0.0019(7) 0.0022(6) 0.0027(7) C19 0.0120(7) 0.0164(9) 0.0157(7) -0.0001(7) 0.0013(5) 0.0035(7) C20 0.0140(8) 0.0152(8) 0.0208(8) 0.0009(7) 0.0024(6) 0.0006(7) C21 0.0161(7) 0.0232(9) 0.0153(7) 0.0032(8) 0.0030(6) 0.0042(8) C22 0.0133(8) 0.0233(9) 0.0161(8) -0.0035(7) 0.0004(6) 0.0054(7) C23 0.0122(8) 0.0171(8) 0.0244(9) -0.0005(7) 0.0015(7) 0.0014(7) C24 0.0145(8) 0.0181(8) 0.0178(8) 0.0024(6) 0.0036(6) 0.0033(7) N1 0.0142(7) 0.0245(7) 0.0152(7) 0.0039(6) 0.0038(5) 0.0041(6) N2 0.0175(8) 0.0311(9) 0.0185(8) -0.0074(7) 0.0009(6) 0.0041(7) O1 0.0317(7) 0.0183(6) 0.0251(7) -0.0007(6) 0.0047(5) 0.0061(6) O2 0.0285(6) 0.0189(7) 0.0139(5) 0.0000(5) 0.0040(5) 0.0050(6) O3 0.0197(6) 0.0331(9) 0.0172(6) -0.0007(5) 0.0062(5) 0.0091(6) O4 0.0273(7) 0.0177(6) 0.0227(7) -0.0026(5) -0.0013(5) 0.0006(6) O5 0.0331(7) 0.0298(7) 0.0306(7) -0.0103(8) -0.0031(5) -0.0041(8) O6 0.0326(8) 0.0398(9) 0.0161(7) -0.0010(6) -0.0013(6) 0.0037(7) S1 0.0171(2) 0.01713(19) 0.01453(18) -0.00137(15) 0.00210(15) 0.00346(15) Br1 0.02036(9) 0.03532(10) 0.01709(8) -0.00166(8) 0.00391(6) -0.00282(9) 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 C1 C2 1.386(3) . ? C1 C6 1.386(3) . ? C1 Br1 1.8918(17) . ? C2 C3 1.398(2) . ? C3 C4 1.389(2) . ? C4 C5 1.394(2) . ? C4 C7 1.491(2) . ? C5 C6 1.385(3) . ? C7 O1 1.199(2) . ? C7 O2 1.341(2) . ? C8 O2 1.4507(19) . ? C8 C9 1.502(3) . ? C9 C10 1.529(3) . ? C9 C12 1.529(2) . ? C10 N1 1.474(2) . ? C11 N1 1.495(2) . ? C11 C13 1.511(2) . ? C11 C12 1.532(3) . ? C13 C14 1.387(3) . ? C13 C18 1.392(3) . ? C14 C15 1.397(3) . ? C15 C16 1.381(3) . ? C16 C17 1.393(3) . ? C17 C18 1.386(3) . ? C19 C20 1.383(2) . ? C19 C24 1.389(3) . ? C19 S1 1.7757(16) . ? C20 C21 1.391(2) . ? C21 C22 1.376(3) . ? C22 C23 1.384(3) . ? C22 N2 1.478(2) . ? C23 C24 1.384(3) . ? N1 S1 1.6075(15) . ? N2 O5 1.220(3) . ? N2 O6 1.223(2) . ? O3 S1 1.4345(13) . ? O4 S1 1.4349(14) . ? 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 121.72(16) . . ? C2 C1 Br1 118.93(14) . . ? C6 C1 Br1 119.35(13) . . ? C1 C2 C3 119.00(16) . . ? C4 C3 C2 119.79(16) . . ? C3 C4 C5 120.17(17) . . ? C3 C4 C7 122.06(16) . . ? C5 C4 C7 117.73(16) . . ? C6 C5 C4 120.39(17) . . ? C5 C6 C1 118.91(16) . . ? O1 C7 O2 124.27(16) . . ? O1 C7 C4 124.84(17) . . ? O2 C7 C4 110.86(15) . . ? O2 C8 C9 105.48(14) . . ? C8 C9 C10 111.86(16) . . ? C8 C9 C12 113.34(15) . . ? C10 C9 C12 104.09(14) . . ? N1 C10 C9 103.13(14) . . ? N1 C11 C13 112.59(14) . . ? N1 C11 C12 100.86(14) . . ? C13 C11 C12 115.21(15) . . ? C9 C12 C11 104.58(14) . . ? C14 C13 C18 118.77(16) . . ? C14 C13 C11 119.63(16) . . ? C18 C13 C11 121.57(16) . . ? C13 C14 C15 120.73(18) . . ? C16 C15 C14 119.95(18) . . ? C15 C16 C17 119.70(17) . . ? C18 C17 C16 120.09(18) . . ? C17 C18 C13 120.72(17) . . ? C20 C19 C24 121.87(16) . . ? C20 C19 S1 119.39(14) . . ? C24 C19 S1 118.73(13) . . ? C19 C20 C21 119.20(17) . . ? C22 C21 C20 117.98(16) . . ? C21 C22 C23 123.73(16) . . ? C21 C22 N2 118.13(16) . . ? C23 C22 N2 118.14(17) . . ? C22 C23 C24 117.84(17) . . ? C23 C24 C19 119.38(16) . . ? C10 N1 C11 113.38(13) . . ? C10 N1 S1 122.52(12) . . ? C11 N1 S1 122.58(12) . . ? O5 N2 O6 124.19(16) . . ? O5 N2 C22 117.70(16) . . ? O6 N2 C22 118.10(16) . . ? C7 O2 C8 116.41(15) . . ? O3 S1 O4 119.58(8) . . ? O3 S1 N1 107.41(8) . . ? O4 S1 N1 109.81(8) . . ? O3 S1 C19 106.86(8) . . ? O4 S1 C19 106.23(8) . . ? N1 S1 C19 106.17(8) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.78 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.524 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.055