# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_chan126 _database_code_depnum_ccdc_archive 'CCDC 850184' #TrackingRef 'chan126.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N O2 S' _chemical_formula_sum 'C20 H21 N O2 S' _chemical_formula_weight 339.44 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6482(3) _cell_length_b 9.8196(4) _cell_length_c 11.8305(5) _cell_angle_alpha 76.306(2) _cell_angle_beta 82.629(2) _cell_angle_gamma 65.289(2) _cell_volume 886.24(6) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6894 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 32.46 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9299 _exptl_absorpt_correction_T_max 0.9513 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21352 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 32.62 _reflns_number_total 6394 _reflns_number_gt 5249 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0557P)^2^+0.2323P] 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 6394 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 C1 C 0.49534(16) 0.19539(15) 0.35780(11) 0.0279(2) Uani 1 1 d . . . H1 H 0.3835 0.2227 0.3342 0.034 Uiso 1 1 calc R . . C2 C 0.63553(15) 0.16112(13) 0.38737(10) 0.0215(2) Uani 1 1 d . . . C3 C 0.80888(14) 0.11306(12) 0.42686(9) 0.0189(2) Uani 1 1 d . . . H3A H 0.8051 0.0953 0.5129 0.023 Uiso 1 1 calc R . . H3B H 0.8828 0.0145 0.4042 0.023 Uiso 1 1 calc R . . C4 C 0.78328(15) 0.38313(13) 0.39353(10) 0.0229(2) Uani 1 1 d . . . H4A H 0.6676 0.4173 0.3650 0.028 Uiso 1 1 calc R . . H4B H 0.8360 0.4511 0.3461 0.028 Uiso 1 1 calc R . . C5 C 0.77073(16) 0.39538(14) 0.52116(11) 0.0263(2) Uani 1 1 d . . . H5A H 0.7019 0.5030 0.5281 0.032 Uiso 1 1 calc R . . H5B H 0.7120 0.3319 0.5677 0.032 Uiso 1 1 calc R . . C6 C 0.94406(16) 0.34320(14) 0.56917(11) 0.0245(2) Uani 1 1 d . . . H6 H 1.0293 0.3628 0.5174 0.029 Uiso 1 1 calc R . . C7 C 0.98755(15) 0.27200(13) 0.67804(10) 0.0230(2) Uani 1 1 d . . . H7 H 0.9033 0.2502 0.7295 0.028 Uiso 1 1 calc R . . C8 C 1.15598(15) 0.22428(12) 0.72511(10) 0.0216(2) Uani 1 1 d . . . C9 C 1.17301(17) 0.19979(14) 0.84566(11) 0.0271(2) Uani 1 1 d . . . H9 H 1.0750 0.2163 0.8962 0.033 Uiso 1 1 calc R . . C10 C 1.33208(19) 0.15155(16) 0.89185(12) 0.0326(3) Uani 1 1 d . . . H10 H 1.3415 0.1370 0.9734 0.039 Uiso 1 1 calc R . . C11 C 1.47609(18) 0.12471(16) 0.81988(13) 0.0333(3) Uani 1 1 d . . . H11 H 1.5846 0.0900 0.8518 0.040 Uiso 1 1 calc R . . C12 C 1.46134(18) 0.14860(17) 0.70105(13) 0.0326(3) Uani 1 1 d . . . H12 H 1.5601 0.1313 0.6513 0.039 Uiso 1 1 calc R . . C13 C 1.30380(16) 0.19749(15) 0.65403(11) 0.0270(2) Uani 1 1 d . . . H13 H 1.2959 0.2131 0.5722 0.032 Uiso 1 1 calc R . . C14 C 0.89577(13) 0.27342(12) 0.14055(9) 0.01719(19) Uani 1 1 d . . . C15 C 0.83111(15) 0.18402(13) 0.10325(10) 0.0223(2) Uani 1 1 d . . . H15 H 0.8532 0.0826 0.1448 0.027 Uiso 1 1 calc R . . C16 C 0.73387(16) 0.24487(14) 0.00454(10) 0.0245(2) Uani 1 1 d . . . H16 H 0.6889 0.1843 -0.0208 0.029 Uiso 1 1 calc R . . C17 C 0.70092(14) 0.39310(13) -0.05811(9) 0.0211(2) Uani 1 1 d . . . C18 C 0.59774(16) 0.45892(15) -0.16626(10) 0.0279(3) Uani 1 1 d . . . H18A H 0.4977 0.5514 -0.1553 0.042 Uiso 1 1 calc R . . H18B H 0.5608 0.3833 -0.1812 0.042 Uiso 1 1 calc R . . H18C H 0.6677 0.4849 -0.2327 0.042 Uiso 1 1 calc R . . C19 C 0.76608(14) 0.48059(13) -0.01842(10) 0.0222(2) Uani 1 1 d . . . H19 H 0.7442 0.5820 -0.0599 0.027 Uiso 1 1 calc R . . C20 C 0.86234(14) 0.42248(13) 0.08059(10) 0.0206(2) Uani 1 1 d . . . H20 H 0.9049 0.4838 0.1071 0.025 Uiso 1 1 calc R . . N1 N 0.88627(12) 0.22395(10) 0.37982(8) 0.01797(17) Uani 1 1 d . . . O1 O 1.10529(10) 0.03531(10) 0.27582(7) 0.02417(18) Uani 1 1 d . . . O2 O 1.11256(11) 0.28853(11) 0.26303(8) 0.0284(2) Uani 1 1 d . . . S1 S 1.01720(3) 0.19783(3) 0.26662(2) 0.01831(7) 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 0.0241(6) 0.0319(6) 0.0278(6) 0.0012(5) -0.0049(5) -0.0140(5) C2 0.0213(5) 0.0232(5) 0.0194(5) -0.0002(4) -0.0020(4) -0.0103(4) C3 0.0180(5) 0.0200(5) 0.0165(5) 0.0006(4) -0.0026(4) -0.0073(4) C4 0.0248(5) 0.0188(5) 0.0228(5) -0.0029(4) -0.0077(4) -0.0052(4) C5 0.0261(6) 0.0260(6) 0.0256(6) -0.0089(4) -0.0037(4) -0.0064(5) C6 0.0284(6) 0.0241(5) 0.0233(5) -0.0065(4) -0.0025(4) -0.0116(5) C7 0.0237(5) 0.0212(5) 0.0220(5) -0.0070(4) 0.0005(4) -0.0060(4) C8 0.0252(5) 0.0172(5) 0.0227(5) -0.0056(4) -0.0019(4) -0.0076(4) C9 0.0305(6) 0.0247(6) 0.0228(5) -0.0071(4) 0.0000(5) -0.0069(5) C10 0.0394(7) 0.0308(6) 0.0264(6) -0.0072(5) -0.0105(5) -0.0095(6) C11 0.0309(7) 0.0325(7) 0.0402(7) -0.0106(5) -0.0105(5) -0.0120(5) C12 0.0264(6) 0.0374(7) 0.0371(7) -0.0098(5) 0.0005(5) -0.0150(5) C13 0.0288(6) 0.0303(6) 0.0231(5) -0.0066(4) 0.0006(4) -0.0129(5) C14 0.0148(4) 0.0206(5) 0.0146(4) 0.0006(3) -0.0019(3) -0.0074(4) C15 0.0278(6) 0.0212(5) 0.0182(5) 0.0009(4) -0.0060(4) -0.0111(4) C16 0.0301(6) 0.0263(6) 0.0195(5) -0.0020(4) -0.0074(4) -0.0131(5) C17 0.0179(5) 0.0269(5) 0.0140(4) -0.0009(4) -0.0012(4) -0.0063(4) C18 0.0255(6) 0.0340(6) 0.0169(5) -0.0003(4) -0.0061(4) -0.0059(5) C19 0.0202(5) 0.0216(5) 0.0200(5) 0.0038(4) -0.0030(4) -0.0074(4) C20 0.0186(5) 0.0216(5) 0.0218(5) 0.0010(4) -0.0028(4) -0.0105(4) N1 0.0188(4) 0.0190(4) 0.0156(4) -0.0009(3) -0.0034(3) -0.0078(3) O1 0.0177(4) 0.0244(4) 0.0219(4) -0.0001(3) -0.0032(3) -0.0020(3) O2 0.0220(4) 0.0372(5) 0.0301(5) 0.0032(4) -0.0084(3) -0.0191(4) S1 0.01349(12) 0.02257(14) 0.01729(12) 0.00099(9) -0.00424(8) -0.00736(10) _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 C1 C2 1.1905(17) . ? C1 H1 0.9500 . ? C2 C3 1.4739(15) . ? C3 N1 1.4732(13) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.4771(14) . ? C4 C5 1.5295(16) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5069(17) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.3294(17) . ? C6 H6 0.9500 . ? C7 C8 1.4715(17) . ? C7 H7 0.9500 . ? C8 C13 1.3994(17) . ? C8 C9 1.4055(17) . ? C9 C10 1.3932(19) . ? C9 H9 0.9500 . ? C10 C11 1.380(2) . ? C10 H10 0.9500 . ? C11 C12 1.383(2) . ? C11 H11 0.9500 . ? C12 C13 1.3847(18) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.3912(15) . ? C14 C20 1.3915(15) . ? C14 S1 1.7618(11) . ? C15 C16 1.3890(16) . ? C15 H15 0.9500 . ? C16 C17 1.3949(16) . ? C16 H16 0.9500 . ? C17 C19 1.3926(17) . ? C17 C18 1.5067(16) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.3884(16) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? N1 S1 1.6347(9) . ? O1 S1 1.4358(9) . ? O2 S1 1.4361(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 C2 C1 H1 180.0 . . ? C1 C2 C3 177.73(12) . . ? N1 C3 C2 114.36(9) . . ? N1 C3 H3A 108.7 . . ? C2 C3 H3A 108.7 . . ? N1 C3 H3B 108.7 . . ? C2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? N1 C4 C5 110.80(9) . . ? N1 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 111.58(10) . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 125.38(12) . . ? C7 C6 H6 117.3 . . ? C5 C6 H6 117.3 . . ? C6 C7 C8 125.13(11) . . ? C6 C7 H7 117.4 . . ? C8 C7 H7 117.4 . . ? C13 C8 C9 117.74(11) . . ? C13 C8 C7 122.26(11) . . ? C9 C8 C7 119.97(11) . . ? C10 C9 C8 120.69(12) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 120.40(12) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.58(13) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 120.55(13) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 121.03(12) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C15 C14 C20 120.57(10) . . ? C15 C14 S1 119.44(8) . . ? C20 C14 S1 119.98(8) . . ? C16 C15 C14 119.17(10) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 121.33(11) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C19 C17 C16 118.36(10) . . ? C19 C17 C18 120.06(10) . . ? C16 C17 C18 121.58(11) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C17 121.25(10) . . ? C20 C19 H19 119.4 . . ? C17 C19 H19 119.4 . . ? C19 C20 C14 119.32(10) . . ? C19 C20 H20 120.3 . . ? C14 C20 H20 120.3 . . ? C3 N1 C4 116.21(9) . . ? C3 N1 S1 118.80(7) . . ? C4 N1 S1 117.64(7) . . ? O1 S1 O2 119.58(5) . . ? O1 S1 N1 106.67(5) . . ? O2 S1 N1 106.52(5) . . ? O1 S1 C14 108.15(5) . . ? O2 S1 C14 107.26(5) . . ? N1 S1 C14 108.23(5) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 32.62 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.508 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.060 data_chan150 _database_code_depnum_ccdc_archive 'CCDC 850185' #TrackingRef 'chan150.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 F N O2 S' _chemical_formula_sum 'C20 H20 F N O2 S' _chemical_formula_weight 357.43 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' F F 0.0171 0.0103 '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 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 28.8723(11) _cell_length_b 8.1821(3) _cell_length_c 17.9935(7) _cell_angle_alpha 90.00 _cell_angle_beta 124.4450(10) _cell_angle_gamma 90.00 _cell_volume 3505.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6454 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 29.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9596 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22939 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5069 _reflns_number_gt 3915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0773P)^2^+1.2931P] 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 5069 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 C1 C 0.33081(6) 0.11834(19) 0.59431(10) 0.0246(3) Uani 1 1 d . . . C2 C 0.33415(8) 0.0806(2) 0.67301(11) 0.0335(4) Uani 1 1 d . . . H2 H 0.3043 0.0223 0.6689 0.040 Uiso 1 1 calc R . . C3 C 0.38034(8) 0.1269(3) 0.75696(11) 0.0359(4) Uani 1 1 d . . . H3 H 0.3828 0.0985 0.8103 0.043 Uiso 1 1 calc R . . C4 C 0.42242(8) 0.2147(2) 0.76140(11) 0.0323(4) Uani 1 1 d . . . C5 C 0.42061(8) 0.2567(3) 0.68622(13) 0.0431(5) Uani 1 1 d . . . H5 H 0.4501 0.3181 0.6908 0.052 Uiso 1 1 calc R . . C6 C 0.37440(8) 0.2070(3) 0.60289(12) 0.0378(4) Uani 1 1 d . . . H6 H 0.3727 0.2347 0.5501 0.045 Uiso 1 1 calc R . . C7 C 0.13603(6) -0.01533(17) 0.09191(9) 0.0184(3) Uani 1 1 d . . . C8 C 0.16216(6) 0.13692(18) 0.11485(10) 0.0207(3) Uani 1 1 d . . . H8 H 0.2001 0.1480 0.1650 0.025 Uiso 1 1 calc R . . C9 C 0.13202(7) 0.27258(18) 0.06337(11) 0.0241(3) Uani 1 1 d . . . H9 H 0.1497 0.3766 0.0789 0.029 Uiso 1 1 calc R . . C10 C 0.07623(7) 0.25907(19) -0.01071(10) 0.0242(3) Uani 1 1 d . . . C11 C 0.05142(6) 0.10413(19) -0.03310(10) 0.0237(3) Uani 1 1 d . . . H11 H 0.0138 0.0924 -0.0840 0.028 Uiso 1 1 calc R . . C12 C 0.08051(6) -0.03249(18) 0.01724(10) 0.0219(3) Uani 1 1 d . . . H12 H 0.0630 -0.1368 0.0013 0.026 Uiso 1 1 calc R . . C13 C 0.04378(8) 0.4072(2) -0.06496(13) 0.0386(5) Uani 1 1 d . . . H13A H 0.0431 0.4115 -0.1200 0.058 Uiso 1 1 calc R . . H13B H 0.0619 0.5060 -0.0292 0.058 Uiso 1 1 calc R . . H13C H 0.0052 0.4006 -0.0810 0.058 Uiso 1 1 calc R . . C14 C 0.10365(6) -0.1588(2) 0.21678(11) 0.0272(4) Uani 1 1 d . . . H14A H 0.0798 -0.2315 0.1645 0.033 Uiso 1 1 calc R . . H14B H 0.0900 -0.0453 0.1981 0.033 Uiso 1 1 calc R . . C15 C 0.09934(7) -0.2080(2) 0.29416(12) 0.0337(4) Uani 1 1 d . . . H15A H 0.0642 -0.1631 0.2834 0.040 Uiso 1 1 calc R . . H15B H 0.0975 -0.3286 0.2960 0.040 Uiso 1 1 calc R . . C16 C 0.14807(7) -0.1478(3) 0.38275(12) 0.0339(4) Uani 1 1 d . . . H16 H 0.1466 -0.1612 0.4338 0.041 Uiso 1 1 calc R . . C17 C 0.19381(6) -0.0763(2) 0.39552(10) 0.0245(3) Uani 1 1 d . . . C18 C 0.20009(6) -0.05466(19) 0.31853(10) 0.0220(3) Uani 1 1 d . . . H18A H 0.1903 0.0588 0.2957 0.026 Uiso 1 1 calc R . . H18B H 0.2396 -0.0747 0.3398 0.026 Uiso 1 1 calc R . . C19 C 0.23878(6) -0.0186(2) 0.48420(10) 0.0273(4) Uani 1 1 d . . . H19 H 0.2356 -0.0428 0.5328 0.033 Uiso 1 1 calc R . . C20 C 0.28410(7) 0.06493(19) 0.50411(10) 0.0244(3) Uani 1 1 d . . . H20 H 0.2865 0.0928 0.4551 0.029 Uiso 1 1 calc R . . F1 F 0.46770(5) 0.26218(15) 0.84396(7) 0.0427(3) Uani 1 1 d . . . N1 N 0.16278(5) -0.17045(15) 0.24530(8) 0.0197(3) Uani 1 1 d . . . O1 O 0.22994(4) -0.17230(14) 0.20135(7) 0.0247(3) Uani 1 1 d . . . O2 O 0.14087(5) -0.32868(13) 0.11197(8) 0.0262(3) Uani 1 1 d . . . S1 S 0.170868(14) -0.18500(4) 0.16234(2) 0.01885(12) 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 0.0231(7) 0.0235(7) 0.0180(7) -0.0015(6) 0.0062(6) 0.0092(6) C2 0.0345(9) 0.0415(10) 0.0231(8) -0.0096(7) 0.0153(7) -0.0025(7) C3 0.0389(10) 0.0446(11) 0.0203(8) -0.0083(8) 0.0144(8) 0.0046(8) C4 0.0285(8) 0.0317(8) 0.0194(8) -0.0070(7) 0.0031(7) 0.0100(7) C5 0.0312(10) 0.0542(12) 0.0285(10) -0.0015(9) 0.0076(8) -0.0085(9) C6 0.0324(9) 0.0483(11) 0.0204(8) 0.0026(8) 0.0075(7) -0.0043(8) C7 0.0170(6) 0.0167(6) 0.0175(7) -0.0019(5) 0.0073(5) 0.0008(5) C8 0.0189(7) 0.0204(7) 0.0158(7) -0.0033(5) 0.0057(6) -0.0031(5) C9 0.0284(8) 0.0159(6) 0.0225(8) -0.0029(6) 0.0110(7) -0.0033(6) C10 0.0271(8) 0.0185(7) 0.0226(8) 0.0010(6) 0.0115(7) 0.0047(6) C11 0.0168(7) 0.0225(7) 0.0227(7) -0.0013(6) 0.0056(6) 0.0020(5) C12 0.0173(7) 0.0177(6) 0.0226(7) -0.0030(6) 0.0064(6) -0.0010(5) C13 0.0371(10) 0.0221(8) 0.0374(10) 0.0063(7) 0.0094(8) 0.0077(7) C14 0.0147(7) 0.0346(8) 0.0251(8) -0.0031(7) 0.0070(6) 0.0026(6) C15 0.0183(7) 0.0498(11) 0.0336(10) -0.0035(8) 0.0150(7) 0.0001(7) C16 0.0239(8) 0.0530(11) 0.0266(9) -0.0035(8) 0.0154(7) 0.0017(8) C17 0.0200(7) 0.0294(8) 0.0205(7) -0.0026(6) 0.0093(6) 0.0059(6) C18 0.0205(7) 0.0220(7) 0.0166(7) -0.0015(6) 0.0062(6) -0.0004(5) C19 0.0236(8) 0.0372(9) 0.0191(7) -0.0017(7) 0.0109(6) 0.0078(6) C20 0.0250(8) 0.0252(8) 0.0167(7) -0.0005(6) 0.0079(6) 0.0073(6) F1 0.0333(6) 0.0481(7) 0.0227(5) -0.0105(5) 0.0014(5) 0.0055(5) N1 0.0149(6) 0.0217(6) 0.0183(6) -0.0009(5) 0.0068(5) 0.0007(4) O1 0.0176(5) 0.0301(6) 0.0227(6) 0.0028(5) 0.0091(5) 0.0067(4) O2 0.0307(6) 0.0156(5) 0.0249(6) -0.0042(4) 0.0112(5) 0.0004(4) S1 0.01731(19) 0.01627(18) 0.01792(19) -0.00094(13) 0.00692(15) 0.00273(12) _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 C1 C6 1.384(3) . ? C1 C2 1.398(2) . ? C1 C20 1.472(2) . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C3 C4 1.374(3) . ? C3 H3 0.9500 . ? C4 F1 1.3675(19) . ? C4 C5 1.368(3) . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.393(2) . ? C7 C12 1.3992(19) . ? C7 S1 1.7616(14) . ? C8 C9 1.391(2) . ? C8 H8 0.9500 . ? C9 C10 1.398(2) . ? C9 H9 0.9500 . ? C10 C11 1.399(2) . ? C10 C13 1.505(2) . ? C11 C12 1.384(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N1 1.4818(19) . ? C14 C15 1.521(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.492(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.341(2) . ? C16 H16 0.9500 . ? C17 C19 1.453(2) . ? C17 C18 1.506(2) . ? C18 N1 1.4795(18) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.333(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? N1 S1 1.6406(14) . ? O1 S1 1.4347(11) . ? O2 S1 1.4373(11) . ? 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 117.74(15) . . ? C6 C1 C20 119.12(16) . . ? C2 C1 C20 123.12(16) . . ? C3 C2 C1 121.03(18) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C4 C3 C2 118.67(17) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? F1 C4 C5 118.77(18) . . ? F1 C4 C3 118.82(17) . . ? C5 C4 C3 122.41(16) . . ? C4 C5 C6 118.0(2) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C1 C6 C5 122.11(18) . . ? C1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C8 C7 C12 120.58(13) . . ? C8 C7 S1 119.90(11) . . ? C12 C7 S1 119.32(11) . . ? C9 C8 C7 119.11(13) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 121.41(14) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C9 C10 C11 118.20(14) . . ? C9 C10 C13 120.90(15) . . ? C11 C10 C13 120.91(14) . . ? C12 C11 C10 121.41(13) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C7 119.28(13) . . ? C11 C12 H12 120.4 . . ? C7 C12 H12 120.4 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 C15 109.92(13) . . ? N1 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? N1 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C16 C15 C14 112.02(15) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 124.71(16) . . ? C17 C16 H16 117.6 . . ? C15 C16 H16 117.6 . . ? C16 C17 C19 120.79(15) . . ? C16 C17 C18 120.89(14) . . ? C19 C17 C18 118.33(14) . . ? N1 C18 C17 109.77(13) . . ? N1 C18 H18A 109.7 . . ? C17 C18 H18A 109.7 . . ? N1 C18 H18B 109.7 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C20 C19 C17 126.38(16) . . ? C20 C19 H19 116.8 . . ? C17 C19 H19 116.8 . . ? C19 C20 C1 126.60(16) . . ? C19 C20 H20 116.7 . . ? C1 C20 H20 116.7 . . ? C18 N1 C14 112.53(12) . . ? C18 N1 S1 116.75(10) . . ? C14 N1 S1 114.75(10) . . ? O1 S1 O2 119.56(7) . . ? O1 S1 N1 106.93(7) . . ? O2 S1 N1 106.74(7) . . ? O1 S1 C7 109.39(7) . . ? O2 S1 C7 107.20(7) . . ? N1 S1 C7 106.27(7) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.566 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.130 data_chan156 _database_code_depnum_ccdc_archive 'CCDC 850186' #TrackingRef 'chan156.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H25 N O2 S' _chemical_formula_sum 'C26 H25 N O2 S' _chemical_formula_weight 415.53 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 8.1540(3) _cell_length_b 11.6860(5) _cell_length_c 22.9788(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.734(3) _cell_angle_gamma 90.00 _cell_volume 2182.13(16) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 4695 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 31.70 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9349 _exptl_absorpt_correction_T_max 0.9380 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20165 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 31.82 _reflns_number_total 7116 _reflns_number_gt 5418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0633P)^2^+0.6188P] 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 7116 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.004 _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 C1 C 0.32416(17) 0.86373(12) 0.57323(6) 0.0207(3) Uani 1 1 d . . . H1A H 0.3226 0.8128 0.6076 0.025 Uiso 1 1 calc R . . H1B H 0.2092 0.8845 0.5603 0.025 Uiso 1 1 calc R . . C2 C 0.42212(17) 0.97145(12) 0.58989(6) 0.0196(3) Uani 1 1 d . . . H2A H 0.4118 1.0260 0.5568 0.024 Uiso 1 1 calc R . . H2B H 0.3755 1.0083 0.6236 0.024 Uiso 1 1 calc R . . C3 C 0.60223(16) 0.94572(11) 0.60546(5) 0.0163(2) Uani 1 1 d . . . C4 C 0.67198(16) 0.87173(11) 0.56119(5) 0.0175(2) Uani 1 1 d . . . C5 C 0.80614(17) 0.89958(13) 0.53490(6) 0.0224(3) Uani 1 1 d . . . H5A H 0.8615 0.9695 0.5443 0.027 Uiso 1 1 calc R . . H5B H 0.8464 0.8495 0.5068 0.027 Uiso 1 1 calc R . . C6 C 0.57059(17) 0.76691(11) 0.54311(6) 0.0196(3) Uani 1 1 d . . . H6A H 0.6177 0.7283 0.5100 0.024 Uiso 1 1 calc R . . H6B H 0.5717 0.7123 0.5761 0.024 Uiso 1 1 calc R . . C7 C 0.68818(16) 0.98698(10) 0.65374(5) 0.0155(2) Uani 1 1 d . . . C8 C 0.86150(16) 0.95603(11) 0.67313(6) 0.0177(2) Uani 1 1 d . . . C9 C 0.91726(17) 0.84309(12) 0.67594(6) 0.0208(3) Uani 1 1 d . . . H9 H 0.8452 0.7826 0.6631 0.025 Uiso 1 1 calc R . . C10 C 1.07827(19) 0.81859(15) 0.69748(6) 0.0293(3) Uani 1 1 d . . . H10 H 1.1156 0.7416 0.6994 0.035 Uiso 1 1 calc R . . C11 C 1.18411(19) 0.90657(19) 0.71616(7) 0.0372(4) Uani 1 1 d . . . H11 H 1.2938 0.8895 0.7308 0.045 Uiso 1 1 calc R . . C12 C 1.1312(2) 1.01823(18) 0.71363(8) 0.0372(4) Uani 1 1 d . . . H12 H 1.2043 1.0783 0.7262 0.045 Uiso 1 1 calc R . . C13 C 0.97026(19) 1.04309(14) 0.69254(7) 0.0277(3) Uani 1 1 d . . . H13 H 0.9338 1.1203 0.6913 0.033 Uiso 1 1 calc R . . C14 C 0.61341(16) 1.07014(10) 0.69320(5) 0.0158(2) Uani 1 1 d . . . C15 C 0.61866(17) 1.04848(11) 0.75300(6) 0.0191(3) Uani 1 1 d . . . H15 H 0.6713 0.9812 0.7684 0.023 Uiso 1 1 calc R . . C16 C 0.54790(19) 1.12408(13) 0.79033(6) 0.0245(3) Uani 1 1 d . . . H16 H 0.5498 1.1073 0.8308 0.029 Uiso 1 1 calc R . . C17 C 0.47464(19) 1.22383(14) 0.76850(7) 0.0284(3) Uani 1 1 d . . . H17 H 0.4253 1.2754 0.7938 0.034 Uiso 1 1 calc R . . C18 C 0.4738(2) 1.24793(13) 0.70938(7) 0.0305(3) Uani 1 1 d . . . H18 H 0.4258 1.3171 0.6944 0.037 Uiso 1 1 calc R . . C19 C 0.54235(19) 1.17196(12) 0.67189(6) 0.0239(3) Uani 1 1 d . . . H19 H 0.5409 1.1894 0.6315 0.029 Uiso 1 1 calc R . . C20 C 0.20856(17) 0.61039(11) 0.53531(6) 0.0199(3) Uani 1 1 d . . . C21 C 0.30222(19) 0.51341(12) 0.54876(6) 0.0239(3) Uani 1 1 d . . . H21 H 0.4047 0.5032 0.5326 0.029 Uiso 1 1 calc R . . C22 C 0.2460(2) 0.43153(12) 0.58582(6) 0.0255(3) Uani 1 1 d . . . H22 H 0.3104 0.3651 0.5946 0.031 Uiso 1 1 calc R . . C23 C 0.09715(19) 0.44471(12) 0.61037(6) 0.0235(3) Uani 1 1 d . . . C24 C 0.0360(2) 0.35576(14) 0.65077(7) 0.0309(3) Uani 1 1 d . . . H24A H 0.0909 0.2827 0.6446 0.046 Uiso 1 1 calc R . . H24B H -0.0832 0.3464 0.6427 0.046 Uiso 1 1 calc R . . H24C H 0.0604 0.3803 0.6913 0.046 Uiso 1 1 calc R . . C25 C 0.0060(2) 0.54308(14) 0.59695(7) 0.0319(3) Uani 1 1 d . . . H25 H -0.0956 0.5538 0.6137 0.038 Uiso 1 1 calc R . . C26 C 0.05952(19) 0.62565(14) 0.55985(7) 0.0298(3) Uani 1 1 d . . . H26 H -0.0048 0.6922 0.5512 0.036 Uiso 1 1 calc R . . N1 N 0.39962(14) 0.80354(10) 0.52576(5) 0.0185(2) Uani 1 1 d . . . O1 O 0.13683(13) 0.77988(9) 0.46560(4) 0.0235(2) Uani 1 1 d . . . O2 O 0.37799(13) 0.65837(9) 0.44754(4) 0.0236(2) Uani 1 1 d . . . S1 S 0.27771(4) 0.71456(3) 0.487430(14) 0.01892(9) 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 0.0189(7) 0.0257(6) 0.0178(6) -0.0050(5) 0.0023(5) 0.0049(5) C2 0.0189(6) 0.0214(6) 0.0180(6) -0.0037(5) -0.0017(5) 0.0069(5) C3 0.0170(6) 0.0169(5) 0.0152(6) 0.0017(4) 0.0027(4) 0.0045(4) C4 0.0183(6) 0.0195(6) 0.0144(5) 0.0012(4) 0.0002(4) 0.0061(5) C5 0.0202(7) 0.0288(7) 0.0187(6) 0.0025(5) 0.0037(5) 0.0067(5) C6 0.0204(7) 0.0197(6) 0.0186(6) -0.0012(4) 0.0013(5) 0.0063(5) C7 0.0167(6) 0.0137(5) 0.0163(6) 0.0024(4) 0.0030(4) 0.0011(4) C8 0.0151(6) 0.0212(6) 0.0170(6) 0.0011(4) 0.0032(4) 0.0005(5) C9 0.0208(7) 0.0243(6) 0.0175(6) 0.0011(5) 0.0032(5) 0.0055(5) C10 0.0242(8) 0.0437(9) 0.0203(7) 0.0036(6) 0.0045(5) 0.0163(7) C11 0.0148(7) 0.0701(13) 0.0267(8) -0.0034(8) 0.0009(6) 0.0078(8) C12 0.0190(8) 0.0540(11) 0.0387(9) -0.0086(8) 0.0039(6) -0.0092(7) C13 0.0208(7) 0.0305(7) 0.0322(8) -0.0031(6) 0.0040(6) -0.0066(6) C14 0.0152(6) 0.0145(5) 0.0178(6) -0.0010(4) 0.0007(4) 0.0002(4) C15 0.0209(7) 0.0184(6) 0.0180(6) 0.0010(4) 0.0015(5) -0.0031(5) C16 0.0265(7) 0.0273(7) 0.0202(6) -0.0063(5) 0.0050(5) -0.0064(6) C17 0.0247(8) 0.0300(7) 0.0306(8) -0.0144(6) 0.0031(6) 0.0018(6) C18 0.0352(9) 0.0222(6) 0.0327(8) -0.0072(6) -0.0056(6) 0.0114(6) C19 0.0309(8) 0.0192(6) 0.0212(6) -0.0008(5) -0.0011(5) 0.0060(5) C20 0.0232(7) 0.0197(6) 0.0166(6) -0.0017(4) 0.0008(5) 0.0020(5) C21 0.0278(8) 0.0244(6) 0.0202(6) 0.0006(5) 0.0059(5) 0.0067(6) C22 0.0340(8) 0.0230(6) 0.0197(6) 0.0023(5) 0.0027(6) 0.0068(6) C23 0.0291(8) 0.0237(6) 0.0177(6) -0.0012(5) 0.0004(5) -0.0036(6) C24 0.0355(9) 0.0330(8) 0.0239(7) 0.0045(6) 0.0019(6) -0.0064(7) C25 0.0266(8) 0.0329(8) 0.0376(9) 0.0045(6) 0.0113(6) 0.0027(6) C26 0.0248(8) 0.0265(7) 0.0390(9) 0.0060(6) 0.0090(6) 0.0077(6) N1 0.0183(6) 0.0192(5) 0.0177(5) -0.0032(4) 0.0006(4) 0.0034(4) O1 0.0245(5) 0.0226(5) 0.0222(5) 0.0007(4) -0.0054(4) 0.0033(4) O2 0.0303(6) 0.0245(5) 0.0165(4) -0.0032(4) 0.0047(4) 0.0025(4) S1 0.02257(18) 0.01894(15) 0.01499(15) -0.00094(11) -0.00004(11) 0.00237(12) _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 C1 N1 1.4744(16) . ? C1 C2 1.523(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5128(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C7 1.3513(18) . ? C3 C4 1.4839(17) . ? C4 C5 1.3328(19) . ? C4 C6 1.5165(19) . ? C5 H5A 0.9500 . ? C5 H5B 0.9500 . ? C6 N1 1.4811(17) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.4908(18) . ? C7 C14 1.4932(17) . ? C8 C9 1.3957(18) . ? C8 C13 1.398(2) . ? C9 C10 1.394(2) . ? C9 H9 0.9500 . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C11 C12 1.374(3) . ? C11 H11 0.9500 . ? C12 C13 1.392(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.3945(18) . ? C14 C15 1.3945(18) . ? C15 C16 1.3896(19) . ? C15 H15 0.9500 . ? C16 C17 1.385(2) . ? C16 H16 0.9500 . ? C17 C18 1.387(2) . ? C17 H17 0.9500 . ? C18 C19 1.386(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.3872(19) . ? C20 C26 1.393(2) . ? C20 S1 1.7642(14) . ? C21 C22 1.384(2) . ? C21 H21 0.9500 . ? C22 C23 1.389(2) . ? C22 H22 0.9500 . ? C23 C25 1.390(2) . ? C23 C24 1.506(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.382(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N1 S1 1.6434(12) . ? O1 S1 1.4348(10) . ? O2 S1 1.4365(10) . ? 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 N1 C1 C2 109.77(11) . . ? N1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? N1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C3 C2 C1 111.97(11) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C7 C3 C4 124.65(12) . . ? C7 C3 C2 123.43(11) . . ? C4 C3 C2 111.91(11) . . ? C5 C4 C3 122.94(13) . . ? C5 C4 C6 121.49(12) . . ? C3 C4 C6 115.30(11) . . ? C4 C5 H5A 120.0 . . ? C4 C5 H5B 120.0 . . ? H5A C5 H5B 120.0 . . ? N1 C6 C4 108.67(10) . . ? N1 C6 H6A 110.0 . . ? C4 C6 H6A 110.0 . . ? N1 C6 H6B 110.0 . . ? C4 C6 H6B 110.0 . . ? H6A C6 H6B 108.3 . . ? C3 C7 C8 124.99(11) . . ? C3 C7 C14 121.37(11) . . ? C8 C7 C14 113.64(11) . . ? C9 C8 C13 118.53(13) . . ? C9 C8 C7 122.71(12) . . ? C13 C8 C7 118.65(12) . . ? C10 C9 C8 120.28(14) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 120.08(15) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 120.38(15) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.78(16) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C8 120.94(15) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C19 C14 C15 118.62(12) . . ? C19 C14 C7 121.39(12) . . ? C15 C14 C7 119.96(11) . . ? C16 C15 C14 120.82(13) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.02(13) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 119.53(13) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C19 C18 C17 120.60(14) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C14 120.36(13) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? C21 C20 C26 119.80(13) . . ? C21 C20 S1 120.29(11) . . ? C26 C20 S1 119.91(11) . . ? C22 C21 C20 119.86(14) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 121.22(14) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C22 C23 C25 118.10(13) . . ? C22 C23 C24 121.27(14) . . ? C25 C23 C24 120.63(14) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C23 121.60(15) . . ? C26 C25 H25 119.2 . . ? C23 C25 H25 119.2 . . ? C25 C26 C20 119.40(14) . . ? C25 C26 H26 120.3 . . ? C20 C26 H26 120.3 . . ? C1 N1 C6 112.32(10) . . ? C1 N1 S1 115.31(9) . . ? C6 N1 S1 118.40(9) . . ? O1 S1 O2 120.10(6) . . ? O1 S1 N1 106.39(6) . . ? O2 S1 N1 106.27(6) . . ? O1 S1 C20 107.29(7) . . ? O2 S1 C20 108.09(6) . . ? N1 S1 C20 108.22(6) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.472 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.062 data_chan177s _database_code_depnum_ccdc_archive 'CCDC 850187' #TrackingRef 'chan177s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 Br2 N O2 S' _chemical_formula_sum 'C26 H23 Br2 N O2 S' _chemical_formula_weight 573.33 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 P2(1)/c 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 14.6259(2) _cell_length_b 8.4133(2) _cell_length_c 18.8218(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.8040(10) _cell_angle_gamma 90.00 _cell_volume 2307.93(7) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 5430 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 29.05 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 3.627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5025 _exptl_absorpt_correction_T_max 0.7130 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27699 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 31.02 _reflns_number_total 7369 _reflns_number_gt 5367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0526P)^2^+0.2105P] 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 7369 _refine_ls_number_parameters 318 _refine_ls_number_restraints 77 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _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 0.019407(15) 0.15710(3) 0.236640(14) 0.02705(8) Uani 1 1 d . A . Br2 Br 0.215705(19) 1.12506(3) 0.503608(13) 0.03119(8) Uani 1 1 d . A . C1 C 0.5059(5) 0.8941(7) 0.0966(4) 0.0265(14) Uani 0.487(7) 1 d PDU A 1 H1A H 0.4627 0.8905 0.0532 0.032 Uiso 0.487(7) 1 calc PR A 1 H1B H 0.5556 0.9698 0.0882 0.032 Uiso 0.487(7) 1 calc PR A 1 C2 C 0.5458(3) 0.7295(6) 0.1124(3) 0.0217(13) Uani 0.487(7) 1 d PDU A 1 H2A H 0.5837 0.6985 0.0735 0.026 Uiso 0.487(7) 1 calc PR A 1 H2B H 0.5865 0.7340 0.1571 0.026 Uiso 0.487(7) 1 calc PR A 1 C3 C 0.4730(5) 0.6038(13) 0.1198(5) 0.0156(17) Uani 0.487(7) 1 d PDU A 1 H3 H 0.4768 0.5153 0.0888 0.019 Uiso 0.487(7) 1 calc PR A 1 C1A C 0.5294(4) 0.8761(7) 0.1256(3) 0.0222(12) Uani 0.513(7) 1 d PDU A 2 H1A1 H 0.5758 0.8341 0.1622 0.027 Uiso 0.513(7) 1 calc PR A 2 H1A2 H 0.5594 0.9582 0.0980 0.027 Uiso 0.513(7) 1 calc PR A 2 C2A C 0.4969(3) 0.7437(6) 0.0766(3) 0.0232(13) Uani 0.513(7) 1 d PDU A 2 H2A1 H 0.4533 0.7895 0.0390 0.028 Uiso 0.513(7) 1 calc PR A 2 H2A2 H 0.5504 0.7044 0.0529 0.028 Uiso 0.513(7) 1 calc PR A 2 C3A C 0.4514(5) 0.6032(12) 0.1072(5) 0.0182(17) Uani 0.513(7) 1 d PDU A 2 H3A H 0.4583 0.5055 0.0829 0.022 Uiso 0.513(7) 1 calc PR A 2 N1 N 0.45486(13) 0.9495(2) 0.16128(12) 0.0254(5) Uani 1 1 d D . . C4 C 0.40347(14) 0.5957(3) 0.16284(12) 0.0177(4) Uani 1 1 d D . . H4A H 0.3783 0.4935 0.1702 0.021 Uiso 0.513(7) 1 calc PR A 2 H4 H 0.3650 0.5047 0.1580 0.021 Uiso 0.487(7) 1 d PR A 1 C5 C 0.38071(14) 0.7134(3) 0.21616(12) 0.0170(4) Uani 1 1 d . A . C6 C 0.43967(16) 0.8613(3) 0.22672(14) 0.0235(5) Uani 1 1 d . A . H6A H 0.4105 0.9337 0.2596 0.028 Uiso 1 1 calc R . . H6B H 0.5001 0.8300 0.2502 0.028 Uiso 1 1 calc R . . C7 C 0.31118(14) 0.6878(3) 0.25832(12) 0.0200(5) Uani 1 1 d . . . C8 C 0.24586(14) 0.5505(3) 0.24985(12) 0.0194(5) Uani 1 1 d . A . C9 C 0.19697(14) 0.5161(3) 0.18471(12) 0.0200(5) Uani 1 1 d . . . H9 H 0.2089 0.5743 0.1433 0.024 Uiso 1 1 calc R A . C10 C 0.13054(15) 0.3963(3) 0.18026(13) 0.0226(5) Uani 1 1 d . A . H10 H 0.0975 0.3721 0.1359 0.027 Uiso 1 1 calc R . . C11 C 0.11350(15) 0.3137(3) 0.24098(13) 0.0209(5) Uani 1 1 d . . . C12 C 0.16162(16) 0.3444(3) 0.30599(13) 0.0239(5) Uani 1 1 d . A . H12 H 0.1498 0.2854 0.3473 0.029 Uiso 1 1 calc R . . C13 C 0.22738(16) 0.4631(3) 0.30951(13) 0.0232(5) Uani 1 1 d . . . H13 H 0.2607 0.4854 0.3539 0.028 Uiso 1 1 calc R A . C14 C 0.29062(15) 0.7937(3) 0.31819(12) 0.0204(5) Uani 1 1 d . A . C15 C 0.20265(15) 0.8569(3) 0.31930(12) 0.0198(5) Uani 1 1 d . . . H15 H 0.1576 0.8323 0.2816 0.024 Uiso 1 1 calc R A . C16 C 0.17938(15) 0.9548(3) 0.37404(12) 0.0209(5) Uani 1 1 d . A . H16 H 0.1196 0.9989 0.3738 0.025 Uiso 1 1 calc R . . C17 C 0.24547(16) 0.9869(3) 0.42934(12) 0.0232(5) Uani 1 1 d . . . C18 C 0.33207(16) 0.9222(3) 0.43126(13) 0.0255(5) Uani 1 1 d . A . H18 H 0.3759 0.9436 0.4702 0.031 Uiso 1 1 calc R . . C19 C 0.35456(16) 0.8257(3) 0.37588(13) 0.0249(5) Uani 1 1 d . . . H19 H 0.4142 0.7806 0.3770 0.030 Uiso 1 1 calc R A . C20 C 0.28288(15) 1.0043(3) 0.09560(12) 0.0202(5) Uani 1 1 d . . . C21 C 0.21024(16) 0.9792(3) 0.13738(13) 0.0247(5) Uani 1 1 d . A . H21 H 0.2145 1.0124 0.1858 0.030 Uiso 1 1 calc R . . C22 C 0.13138(17) 0.9050(3) 0.10755(14) 0.0277(6) Uani 1 1 d . . . H22 H 0.0818 0.8868 0.1361 0.033 Uiso 1 1 calc R A . C23 C 0.12377(17) 0.8569(3) 0.03663(14) 0.0274(5) Uani 1 1 d . A . C24 C 0.03752(19) 0.7749(4) 0.00525(16) 0.0399(7) Uani 1 1 d . . . H24A H 0.0281 0.7986 -0.0458 0.060 Uiso 1 1 calc R A . H24B H -0.0152 0.8131 0.0292 0.060 Uiso 1 1 calc R . . H24C H 0.0438 0.6598 0.0120 0.060 Uiso 1 1 calc R . . C25 C 0.19659(18) 0.8855(3) -0.00426(13) 0.0280(6) Uani 1 1 d . . . H25 H 0.1919 0.8539 -0.0529 0.034 Uiso 1 1 calc R A . C26 C 0.27597(17) 0.9591(3) 0.02434(13) 0.0256(5) Uani 1 1 d . A . H26 H 0.3252 0.9784 -0.0044 0.031 Uiso 1 1 calc R . . O1 O 0.36114(11) 1.1756(2) 0.19642(9) 0.0260(4) Uani 1 1 d . . . O2 O 0.42801(13) 1.1732(2) 0.07967(11) 0.0349(5) Uani 1 1 d . . . S1 S 0.38506(4) 1.09089(7) 0.13473(3) 0.02087(13) Uani 1 1 d . A . 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 0.01357(10) 0.03021(15) 0.03729(15) 0.00485(11) 0.00171(9) -0.00494(9) Br2 0.03896(15) 0.03283(16) 0.02155(13) -0.00980(11) 0.00111(11) 0.00948(11) C1 0.028(3) 0.024(3) 0.029(3) 0.009(3) 0.014(3) 0.010(2) C2 0.018(2) 0.016(2) 0.031(3) 0.002(2) 0.006(2) 0.0031(18) C3 0.019(4) 0.019(3) 0.008(3) -0.004(2) -0.005(3) 0.003(3) C1A 0.016(2) 0.022(3) 0.030(3) 0.006(2) 0.007(2) 0.0016(19) C2A 0.024(2) 0.022(2) 0.025(3) 0.0020(19) 0.009(2) 0.0042(18) C3A 0.022(4) 0.015(3) 0.016(3) 0.001(2) -0.008(3) -0.001(3) N1 0.0167(9) 0.0170(10) 0.0434(13) -0.0028(9) 0.0072(8) -0.0028(8) C4 0.0153(9) 0.0155(11) 0.0215(11) -0.0001(9) -0.0028(8) -0.0006(8) C5 0.0157(9) 0.0133(10) 0.0211(11) -0.0011(9) -0.0048(8) -0.0002(8) C6 0.0178(10) 0.0169(12) 0.0342(13) -0.0040(10) -0.0075(9) 0.0008(9) C7 0.0154(9) 0.0222(12) 0.0212(11) -0.0061(9) -0.0049(8) 0.0004(9) C8 0.0135(9) 0.0244(13) 0.0204(11) -0.0061(9) 0.0021(8) -0.0004(8) C9 0.0161(10) 0.0267(13) 0.0176(11) -0.0032(9) 0.0042(8) -0.0042(9) C10 0.0172(10) 0.0312(14) 0.0193(11) -0.0016(10) 0.0012(9) -0.0053(9) C11 0.0129(9) 0.0225(12) 0.0280(12) 0.0003(10) 0.0053(8) -0.0024(8) C12 0.0201(10) 0.0280(14) 0.0237(12) 0.0009(10) 0.0030(9) 0.0000(9) C13 0.0214(11) 0.0277(13) 0.0200(11) -0.0029(10) -0.0022(9) 0.0001(10) C14 0.0157(10) 0.0234(13) 0.0216(11) -0.0068(9) -0.0022(8) 0.0017(9) C15 0.0146(9) 0.0252(13) 0.0190(11) -0.0039(9) -0.0033(8) 0.0010(8) C16 0.0175(10) 0.0260(13) 0.0192(11) -0.0021(10) 0.0008(8) 0.0049(9) C17 0.0276(12) 0.0248(13) 0.0168(11) -0.0065(9) 0.0003(9) 0.0043(10) C18 0.0222(11) 0.0301(14) 0.0225(12) -0.0069(10) -0.0079(9) 0.0021(10) C19 0.0173(10) 0.0282(14) 0.0280(13) -0.0073(10) -0.0049(9) 0.0057(9) C20 0.0205(10) 0.0179(11) 0.0218(11) -0.0007(9) -0.0006(9) -0.0059(9) C21 0.0229(11) 0.0328(15) 0.0183(11) -0.0028(10) 0.0019(9) -0.0058(10) C22 0.0222(11) 0.0343(15) 0.0269(13) -0.0007(11) 0.0037(10) -0.0085(11) C23 0.0258(11) 0.0273(14) 0.0283(13) -0.0010(11) -0.0025(10) -0.0092(10) C24 0.0297(14) 0.0452(19) 0.0435(17) -0.0087(14) -0.0054(12) -0.0175(13) C25 0.0333(13) 0.0293(14) 0.0210(12) -0.0060(10) 0.0000(10) -0.0114(11) C26 0.0282(12) 0.0282(14) 0.0211(12) -0.0012(10) 0.0067(9) -0.0102(10) O1 0.0234(8) 0.0199(9) 0.0331(10) -0.0111(7) -0.0067(7) 0.0036(7) O2 0.0316(10) 0.0323(11) 0.0403(11) 0.0045(9) -0.0002(8) -0.0192(8) S1 0.0193(2) 0.0159(3) 0.0269(3) -0.0025(2) -0.0009(2) -0.0060(2) _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 C11 1.902(2) . ? Br2 C17 1.896(2) . ? C1 C2 1.522(7) . ? C1 N1 1.552(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.516(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.354(8) . ? C3 H3 0.9500 . ? C1A N1 1.464(5) . ? C1A C2A 1.499(7) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A C3A 1.495(9) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4 1.310(9) . ? C3A H3A 0.9500 . ? N1 C6 1.471(3) . ? N1 S1 1.619(2) . ? C4 C5 1.468(3) . ? C4 H4A 0.9500 . ? C4 H4 0.9500 . ? C5 C7 1.358(3) . ? C5 C6 1.517(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C14 1.487(3) . ? C7 C8 1.499(3) . ? C8 C13 1.387(3) . ? C8 C9 1.397(3) . ? C9 C10 1.397(3) . ? C9 H9 0.9500 . ? C10 C11 1.378(3) . ? C10 H10 0.9500 . ? C11 C12 1.384(3) . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.394(3) . ? C14 C19 1.399(3) . ? C15 C16 1.383(3) . ? C15 H15 0.9500 . ? C16 C17 1.386(3) . ? C16 H16 0.9500 . ? C17 C18 1.376(3) . ? C18 C19 1.382(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C26 1.390(3) . ? C20 C21 1.390(3) . ? C20 S1 1.767(2) . ? C21 C22 1.388(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(4) . ? C22 H22 0.9500 . ? C23 C25 1.386(4) . ? C23 C24 1.514(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.384(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O1 S1 1.4307(18) . ? O2 S1 1.4344(19) . ? 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 N1 108.8(4) . . ? C2 C1 H1A 109.9 . . ? N1 C1 H1A 109.9 . . ? C2 C1 H1B 109.9 . . ? N1 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? C3 C2 C1 113.0(6) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 131.2(8) . . ? C4 C3 H3 114.4 . . ? C2 C3 H3 114.4 . . ? N1 C1A C2A 112.7(4) . . ? N1 C1A H1A1 109.1 . . ? C2A C1A H1A1 109.1 . . ? N1 C1A H1A2 109.1 . . ? C2A C1A H1A2 109.1 . . ? H1A1 C1A H1A2 107.8 . . ? C3A C2A C1A 118.6(5) . . ? C3A C2A H2A1 107.7 . . ? C1A C2A H2A1 107.7 . . ? C3A C2A H2A2 107.7 . . ? C1A C2A H2A2 107.7 . . ? H2A1 C2A H2A2 107.1 . . ? C4 C3A C2A 129.1(8) . . ? C4 C3A H3A 115.4 . . ? C2A C3A H3A 115.4 . . ? C1A N1 C6 110.0(3) . . ? C1A N1 C1 24.2(2) . . ? C6 N1 C1 128.4(3) . . ? C1A N1 S1 130.0(3) . . ? C6 N1 S1 119.58(16) . . ? C1 N1 S1 108.1(3) . . ? C3A C4 C3 16.2(5) . . ? C3A C4 C5 133.0(5) . . ? C3 C4 C5 126.9(5) . . ? C3A C4 H4A 113.5 . . ? C3 C4 H4A 116.8 . . ? C5 C4 H4A 113.5 . . ? C3A C4 H4 108.4 . . ? C3 C4 H4 116.9 . . ? C5 C4 H4 116.2 . . ? H4A C4 H4 18.3 . . ? C7 C5 C4 121.1(2) . . ? C7 C5 C6 119.9(2) . . ? C4 C5 C6 118.9(2) . . ? N1 C6 C5 115.3(2) . . ? N1 C6 H6A 108.4 . . ? C5 C6 H6A 108.4 . . ? N1 C6 H6B 108.4 . . ? C5 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C5 C7 C14 123.8(2) . . ? C5 C7 C8 124.2(2) . . ? C14 C7 C8 112.0(2) . . ? C13 C8 C9 118.7(2) . . ? C13 C8 C7 119.2(2) . . ? C9 C8 C7 121.9(2) . . ? C8 C9 C10 120.3(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 119.1(2) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 121.7(2) . . ? C10 C11 Br1 119.61(17) . . ? C12 C11 Br1 118.68(18) . . ? C11 C12 C13 118.5(2) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C12 C13 C8 121.7(2) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? C15 C14 C19 118.2(2) . . ? C15 C14 C7 119.05(19) . . ? C19 C14 C7 122.6(2) . . ? C16 C15 C14 121.5(2) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C17 118.4(2) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C18 C17 C16 121.6(2) . . ? C18 C17 Br2 119.39(17) . . ? C16 C17 Br2 118.96(18) . . ? C17 C18 C19 119.3(2) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C14 120.8(2) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? C26 C20 C21 120.5(2) . . ? C26 C20 S1 120.38(18) . . ? C21 C20 S1 119.13(18) . . ? C22 C21 C20 119.2(2) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 121.1(2) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C25 C23 C22 118.6(2) . . ? C25 C23 C24 121.1(2) . . ? C22 C23 C24 120.3(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C23 121.3(2) . . ? C26 C25 H25 119.3 . . ? C23 C25 H25 119.3 . . ? C25 C26 C20 119.2(2) . . ? C25 C26 H26 120.4 . . ? C20 C26 H26 120.4 . . ? O1 S1 O2 119.83(12) . . ? O1 S1 N1 107.85(11) . . ? O2 S1 N1 105.94(12) . . ? O1 S1 C20 106.74(11) . . ? O2 S1 C20 107.71(11) . . ? N1 S1 C20 108.37(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 31.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.551 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.117