# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Choon-Hong Tan' _publ_contact_author_email CHMTANCH@NUS.EDU.SG _publ_section_title ; Tandem Conjugate Addition-Elimination Reaction Promoted by Chiral Pyrrolidinyl Sulphonamide (CPS)a ; loop_ _publ_author_name 'Choon-Hong Tan.' 'Xiao Fu.' 'Yong-Peng Goh.' 'Zhiyong Jiang.' ; Ruijuan Low ; 'Junye Xu.' # Attachment '11.cif' data_8430 _database_code_depnum_ccdc_archive 'CCDC 692929' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H28 O3 S2' _chemical_formula_weight 344.51 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' 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.7296(18) _cell_length_b 11.309(2) _cell_length_c 11.780(2) _cell_angle_alpha 65.152(4) _cell_angle_beta 68.166(4) _cell_angle_gamma 64.564(4) _cell_volume 1032.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2203 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 19.35 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9149 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details 'Sadabs, (sheldrik 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 area detector' _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 11759 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7994 _reflns_number_gt 5534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. The flack value indicates that the absolute structure reported is correct. ; _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^)+(0.1082P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.17(11) _chemical_absolute_configuration ad _refine_ls_number_reflns 7994 _refine_ls_number_parameters 411 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1174 _refine_ls_R_factor_gt 0.0860 _refine_ls_wR_factor_ref 0.2129 _refine_ls_wR_factor_gt 0.1925 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 S1 S 0.85501(16) 0.75341(18) 0.84748(16) 0.0759(5) Uani 1 1 d . . . S2 S 1.06182(17) 0.38159(16) 0.79332(17) 0.0768(5) Uani 1 1 d . . . S3 S 0.62697(18) 0.52431(19) 0.4818(2) 0.0855(6) Uani 1 1 d . . . S4 S 0.47102(18) 0.92420(16) 0.43234(17) 0.0751(5) Uani 1 1 d . . . O1 O 0.9989(12) 0.8770(7) 0.1951(6) 0.160(3) Uani 1 1 d . . . O2 O 0.6661(5) 0.8048(5) 0.7076(4) 0.0841(14) Uani 1 1 d . . . O3 O 0.7792(5) 0.4857(5) 0.7553(5) 0.0881(14) Uani 1 1 d . . . O4 O 0.3164(9) 0.4925(7) 1.0870(5) 0.147(3) Uani 1 1 d . . . O5 O 0.3239(5) 0.5653(5) 0.5648(4) 0.0785(12) Uani 1 1 d . . . O6 O 0.1985(5) 0.8804(5) 0.5380(4) 0.0826(12) Uani 1 1 d . . . C1 C 0.9215(5) 0.6458(5) 0.6580(5) 0.0475(11) Uani 1 1 d . . . H1 H 1.0241 0.6423 0.6577 0.057 Uiso 1 1 calc R . . C2 C 0.9113(6) 0.6849(5) 0.5204(5) 0.0521(12) Uani 1 1 d . . . H2 H 0.8013 0.7111 0.5205 0.062 Uiso 1 1 calc R . . C3 C 0.9711(7) 0.8036(6) 0.4253(6) 0.0636(14) Uani 1 1 d . . . H3 H 1.0743 0.7824 0.4378 0.076 Uiso 1 1 calc R . . C4 C 0.9992(10) 0.7860(8) 0.2964(6) 0.092(2) Uani 1 1 d . . . C5 C 1.0129(10) 0.6418(7) 0.3180(6) 0.090(2) Uani 1 1 d . . . H5A H 1.1109 0.5977 0.2665 0.108 Uiso 1 1 calc R . . H5B H 0.9271 0.6408 0.2956 0.108 Uiso 1 1 calc R . . C6 C 1.0069(7) 0.5702(6) 0.4583(5) 0.0618(14) Uani 1 1 d . . . H6A H 1.1114 0.5264 0.4737 0.074 Uiso 1 1 calc R . . H6B H 0.9563 0.5008 0.4917 0.074 Uiso 1 1 calc R . . C7 C 0.8797(9) 0.9463(6) 0.4306(7) 0.0784(17) Uani 1 1 d . . . H7A H 0.7710 0.9637 0.4402 0.118 Uiso 1 1 calc R . . H7B H 0.9168 1.0106 0.3525 0.118 Uiso 1 1 calc R . . H7C H 0.8923 0.9569 0.5025 0.118 Uiso 1 1 calc R . . C8 C 0.7940(6) 0.7461(6) 0.7266(5) 0.0558(13) Uani 1 1 d . . . C9 C 0.6793(8) 0.8574(8) 0.9396(7) 0.0787(19) Uani 1 1 d . . . C10 C 0.6326(13) 1.0028(9) 0.8579(11) 0.134(4) Uani 1 1 d . . . H10A H 0.5949 1.0098 0.7900 0.202 Uiso 1 1 calc R . . H10B H 0.7213 1.0347 0.8217 0.202 Uiso 1 1 calc R . . H10C H 0.5512 1.0583 0.9093 0.202 Uiso 1 1 calc R . . C11 C 0.5478(9) 0.8007(11) 0.9879(8) 0.108(3) Uani 1 1 d . . . H11A H 0.4688 0.8399 1.0524 0.162 Uiso 1 1 calc R . . H11B H 0.5864 0.7024 1.0244 0.162 Uiso 1 1 calc R . . H11C H 0.5037 0.8234 0.9178 0.162 Uiso 1 1 calc R . . C12 C 0.7380(10) 0.8421(12) 1.0506(10) 0.126(4) Uani 1 1 d . . . H12A H 0.8308 0.8681 1.0166 0.189 Uiso 1 1 calc R . . H12B H 0.7616 0.7480 1.1049 0.189 Uiso 1 1 calc R . . H12C H 0.6585 0.9005 1.0999 0.189 Uiso 1 1 calc R . . C13 C 0.8984(6) 0.5049(6) 0.7394(5) 0.0555(13) Uani 1 1 d . . . C14 C 1.0086(9) 0.2240(8) 0.8939(8) 0.097(3) Uani 1 1 d . . . C15 C 0.9674(14) 0.1745(11) 0.8179(15) 0.156(5) Uani 1 1 d . . . H15A H 0.9756 0.0792 0.8608 0.234 Uiso 1 1 calc R . . H15B H 1.0376 0.1843 0.7343 0.234 Uiso 1 1 calc R . . H15C H 0.8620 0.2275 0.8089 0.234 Uiso 1 1 calc R . . C16 C 1.1591(13) 0.1240(10) 0.9340(15) 0.171(6) Uani 1 1 d . . . H16A H 1.1523 0.0326 0.9726 0.256 Uiso 1 1 calc R . . H16B H 1.1752 0.1494 0.9951 0.256 Uiso 1 1 calc R . . H16C H 1.2451 0.1266 0.8598 0.256 Uiso 1 1 calc R . . C17 C 0.8722(14) 0.2551(12) 1.0064(10) 0.157(5) Uani 1 1 d . . . H17A H 0.7771 0.3060 0.9770 0.235 Uiso 1 1 calc R . . H17B H 0.8903 0.3085 1.0414 0.235 Uiso 1 1 calc R . . H17C H 0.8633 0.1702 1.0717 0.235 Uiso 1 1 calc R . . C18 C 0.4123(5) 0.6968(5) 0.6197(5) 0.0484(12) Uani 1 1 d . . . H18 H 0.5159 0.6916 0.6187 0.058 Uiso 1 1 calc R . . C19 C 0.3145(6) 0.6703(5) 0.7577(5) 0.0523(12) Uani 1 1 d . . . H19 H 0.2211 0.6557 0.7600 0.063 Uiso 1 1 calc R . . C20 C 0.4001(7) 0.5442(6) 0.8569(6) 0.0627(14) Uani 1 1 d . . . H20 H 0.5044 0.5500 0.8379 0.075 Uiso 1 1 calc R . . C21 C 0.3115(8) 0.5739(8) 0.9836(7) 0.0816(19) Uani 1 1 d . . . C22 C 0.2153(9) 0.7244(7) 0.9552(7) 0.086(2) Uani 1 1 d . . . H22A H 0.1045 0.7355 0.9825 0.103 Uiso 1 1 calc R . . H22B H 0.2367 0.7672 1.0001 0.103 Uiso 1 1 calc R . . C23 C 0.2611(7) 0.7884(6) 0.8133(6) 0.0679(15) Uani 1 1 d . . . H23A H 0.3456 0.8240 0.7907 0.082 Uiso 1 1 calc R . . H23B H 0.1729 0.8630 0.7814 0.082 Uiso 1 1 calc R . . C24 C 0.4245(11) 0.4021(7) 0.8617(8) 0.095(2) Uani 1 1 d . . . H24A H 0.4726 0.3355 0.9312 0.143 Uiso 1 1 calc R . . H24B H 0.4912 0.3865 0.7820 0.143 Uiso 1 1 calc R . . H24C H 0.3254 0.3934 0.8749 0.143 Uiso 1 1 calc R . . C25 C 0.4312(6) 0.5928(5) 0.5595(5) 0.0537(12) Uani 1 1 d . . . C26 C 0.6259(10) 0.4036(8) 0.4151(8) 0.094(2) Uani 1 1 d . . . C27 C 0.5734(14) 0.2886(9) 0.5212(11) 0.129(3) Uani 1 1 d . . . H27A H 0.4648 0.3241 0.5608 0.193 Uiso 1 1 calc R . . H27B H 0.6344 0.2481 0.5842 0.193 Uiso 1 1 calc R . . H27C H 0.5874 0.2201 0.4865 0.193 Uiso 1 1 calc R . . C28 C 0.7978(14) 0.3519(14) 0.3456(15) 0.178(6) Uani 1 1 d . . . H28A H 0.8606 0.2964 0.4078 0.267 Uiso 1 1 calc R . . H28B H 0.8327 0.4293 0.2889 0.267 Uiso 1 1 calc R . . H28C H 0.8077 0.2978 0.2966 0.267 Uiso 1 1 calc R . . C29 C 0.5250(15) 0.4795(10) 0.3202(9) 0.131(3) Uani 1 1 d . . . H29A H 0.5277 0.4167 0.2837 0.197 Uiso 1 1 calc R . . H29B H 0.5632 0.5511 0.2531 0.197 Uiso 1 1 calc R . . H29C H 0.4193 0.5194 0.3629 0.197 Uiso 1 1 calc R . . C30 C 0.3342(6) 0.8381(6) 0.5351(5) 0.0576(13) Uani 1 1 d . . . C31 C 0.3623(8) 1.0931(6) 0.3353(6) 0.0734(17) Uani 1 1 d . . . C32 C 0.2515(13) 1.1774(9) 0.4200(10) 0.126(3) Uani 1 1 d . . . H32A H 0.1982 1.2666 0.3689 0.189 Uiso 1 1 calc R . . H32B H 0.3078 1.1873 0.4654 0.189 Uiso 1 1 calc R . . H32C H 0.1765 1.1329 0.4806 0.189 Uiso 1 1 calc R . . C33 C 0.4956(11) 1.1536(8) 0.2474(8) 0.105(3) Uani 1 1 d . . . H33A H 0.5651 1.0994 0.1913 0.157 Uiso 1 1 calc R . . H33B H 0.5527 1.1523 0.2994 0.157 Uiso 1 1 calc R . . H33C H 0.4519 1.2468 0.1969 0.157 Uiso 1 1 calc R . . C34 C 0.2854(12) 1.0798(10) 0.2561(8) 0.110(3) Uani 1 1 d . . . H34A H 0.1866 1.0671 0.3071 0.165 Uiso 1 1 calc R . . H34B H 0.3509 1.0017 0.2260 0.165 Uiso 1 1 calc R . . H34C H 0.2687 1.1617 0.1837 0.165 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 S1 0.0562(8) 0.1054(13) 0.0791(11) -0.0544(10) -0.0215(7) -0.0076(8) S2 0.0599(9) 0.0649(9) 0.0945(12) 0.0023(8) -0.0367(8) -0.0213(7) S3 0.0573(9) 0.0894(12) 0.1216(15) -0.0648(11) -0.0032(9) -0.0180(8) S4 0.0681(9) 0.0620(9) 0.0847(11) 0.0024(8) -0.0301(8) -0.0261(7) O1 0.295(10) 0.098(4) 0.055(3) -0.006(3) -0.012(4) -0.078(5) O2 0.054(2) 0.116(4) 0.077(3) -0.047(3) -0.029(2) 0.006(2) O3 0.057(3) 0.091(3) 0.106(4) 0.001(3) -0.026(2) -0.040(2) O4 0.193(7) 0.119(5) 0.047(3) -0.012(3) -0.025(3) 0.006(4) O5 0.062(2) 0.097(3) 0.102(3) -0.045(3) -0.013(2) -0.040(2) O6 0.053(2) 0.089(3) 0.084(3) -0.008(2) -0.024(2) -0.015(2) C1 0.036(2) 0.055(3) 0.053(3) -0.022(2) -0.011(2) -0.010(2) C2 0.042(2) 0.057(3) 0.057(3) -0.015(2) -0.016(2) -0.014(2) C3 0.058(3) 0.062(3) 0.070(4) -0.009(3) -0.022(3) -0.024(3) C4 0.125(6) 0.089(5) 0.043(4) -0.016(4) -0.004(4) -0.036(4) C5 0.136(6) 0.073(4) 0.054(4) -0.025(3) -0.005(4) -0.037(4) C6 0.067(3) 0.057(3) 0.060(3) -0.018(3) -0.019(3) -0.015(3) C7 0.097(5) 0.059(4) 0.073(4) -0.015(3) -0.025(4) -0.021(3) C8 0.041(3) 0.067(3) 0.052(3) -0.018(3) -0.013(2) -0.009(2) C9 0.072(4) 0.101(5) 0.073(4) -0.053(4) -0.008(3) -0.019(4) C10 0.137(8) 0.076(6) 0.155(9) -0.047(6) -0.025(7) -0.001(5) C11 0.075(5) 0.171(9) 0.082(5) -0.053(6) -0.002(4) -0.044(5) C12 0.093(6) 0.188(10) 0.137(8) -0.122(8) -0.025(5) -0.013(6) C13 0.049(3) 0.062(3) 0.044(3) -0.007(2) -0.008(2) -0.018(2) C14 0.082(5) 0.069(4) 0.101(6) 0.012(4) -0.016(4) -0.031(4) C15 0.159(10) 0.095(7) 0.227(14) -0.048(8) -0.034(9) -0.063(7) C16 0.135(9) 0.086(6) 0.224(14) 0.049(8) -0.089(9) -0.031(6) C17 0.166(10) 0.140(9) 0.079(6) 0.009(6) 0.004(6) -0.046(8) C18 0.036(2) 0.056(3) 0.056(3) -0.014(2) -0.014(2) -0.019(2) C19 0.039(2) 0.058(3) 0.056(3) -0.011(2) -0.015(2) -0.015(2) C20 0.053(3) 0.069(4) 0.060(3) -0.019(3) -0.014(3) -0.014(3) C21 0.083(4) 0.090(5) 0.051(4) -0.014(4) -0.017(3) -0.016(4) C22 0.083(4) 0.088(5) 0.077(5) -0.038(4) -0.015(4) -0.010(4) C23 0.061(3) 0.075(4) 0.068(4) -0.035(3) -0.013(3) -0.011(3) C24 0.133(7) 0.067(4) 0.079(5) 0.002(4) -0.042(5) -0.036(4) C25 0.049(3) 0.056(3) 0.054(3) -0.016(2) -0.010(2) -0.018(2) C26 0.112(6) 0.078(5) 0.099(6) -0.054(5) -0.009(5) -0.024(4) C27 0.189(10) 0.061(4) 0.128(7) -0.030(5) -0.048(7) -0.024(5) C28 0.150(10) 0.169(11) 0.221(15) -0.156(12) 0.027(9) -0.022(8) C29 0.200(10) 0.116(7) 0.084(6) -0.036(5) -0.038(7) -0.049(7) C30 0.050(3) 0.065(3) 0.058(3) -0.018(3) -0.018(2) -0.014(3) C31 0.095(5) 0.050(3) 0.064(4) -0.005(3) -0.034(3) -0.012(3) C32 0.152(9) 0.082(5) 0.113(7) -0.041(5) -0.032(6) 0.002(5) C33 0.135(7) 0.076(5) 0.088(5) 0.009(4) -0.033(5) -0.048(5) C34 0.141(7) 0.110(6) 0.086(5) -0.005(5) -0.064(5) -0.040(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 S1 C8 1.777(5) . ? S1 C9 1.857(6) . ? S2 C13 1.726(5) . ? S2 C14 1.847(7) . ? S3 C25 1.760(5) . ? S3 C26 1.844(7) . ? S4 C30 1.763(6) . ? S4 C31 1.844(6) . ? O1 C4 1.205(9) . ? O2 C8 1.188(6) . ? O3 C13 1.203(6) . ? O4 C21 1.181(8) . ? O5 C25 1.186(6) . ? O6 C30 1.188(6) . ? C1 C8 1.515(7) . ? C1 C2 1.520(7) . ? C1 C13 1.540(8) . ? C2 C3 1.522(8) . ? C2 C6 1.530(8) . ? C3 C7 1.486(9) . ? C3 C4 1.523(9) . ? C4 C5 1.494(10) . ? C5 C6 1.495(9) . ? C9 C10 1.480(12) . ? C9 C11 1.492(10) . ? C9 C12 1.532(10) . ? C14 C15 1.469(15) . ? C14 C16 1.512(12) . ? C14 C17 1.524(13) . ? C18 C30 1.519(7) . ? C18 C19 1.524(7) . ? C18 C25 1.529(7) . ? C19 C23 1.538(8) . ? C19 C20 1.548(8) . ? C20 C24 1.500(10) . ? C20 C21 1.516(9) . ? C21 C22 1.507(10) . ? C22 C23 1.491(10) . ? C26 C29 1.495(13) . ? C26 C27 1.498(13) . ? C26 C28 1.534(14) . ? C31 C32 1.478(10) . ? C31 C34 1.479(10) . ? C31 C33 1.546(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 C8 S1 C9 106.6(3) . . ? C13 S2 C14 106.7(3) . . ? C25 S3 C26 105.6(3) . . ? C30 S4 C31 107.1(3) . . ? C8 C1 C2 112.3(4) . . ? C8 C1 C13 105.1(4) . . ? C2 C1 C13 111.2(4) . . ? C1 C2 C3 114.9(4) . . ? C1 C2 C6 114.5(4) . . ? C3 C2 C6 102.8(4) . . ? C7 C3 C2 119.9(5) . . ? C7 C3 C4 114.0(5) . . ? C2 C3 C4 102.3(5) . . ? O1 C4 C5 125.8(7) . . ? O1 C4 C3 125.0(7) . . ? C5 C4 C3 109.1(6) . . ? C4 C5 C6 105.2(5) . . ? C5 C6 C2 104.4(5) . . ? O2 C8 C1 123.9(5) . . ? O2 C8 S1 124.5(4) . . ? C1 C8 S1 111.4(3) . . ? C10 C9 C11 110.8(8) . . ? C10 C9 C12 111.1(8) . . ? C11 C9 C12 111.4(7) . . ? C10 C9 S1 109.9(6) . . ? C11 C9 S1 110.9(5) . . ? C12 C9 S1 102.6(5) . . ? O3 C13 C1 121.1(5) . . ? O3 C13 S2 125.5(4) . . ? C1 C13 S2 113.2(4) . . ? C15 C14 C16 110.5(10) . . ? C15 C14 C17 110.7(9) . . ? C16 C14 C17 113.5(10) . . ? C15 C14 S2 110.8(7) . . ? C16 C14 S2 102.1(6) . . ? C17 C14 S2 108.9(7) . . ? C30 C18 C19 110.8(4) . . ? C30 C18 C25 106.3(4) . . ? C19 C18 C25 112.0(4) . . ? C18 C19 C23 114.3(5) . . ? C18 C19 C20 114.5(4) . . ? C23 C19 C20 103.0(4) . . ? C24 C20 C21 113.8(6) . . ? C24 C20 C19 119.2(5) . . ? C21 C20 C19 103.7(5) . . ? O4 C21 C22 125.9(7) . . ? O4 C21 C20 125.7(7) . . ? C22 C21 C20 108.4(6) . . ? C23 C22 C21 106.5(5) . . ? C22 C23 C19 104.5(5) . . ? O5 C25 C18 122.5(5) . . ? O5 C25 S3 125.6(4) . . ? C18 C25 S3 111.9(4) . . ? C29 C26 C27 111.9(8) . . ? C29 C26 C28 110.0(9) . . ? C27 C26 C28 111.7(8) . . ? C29 C26 S3 109.9(6) . . ? C27 C26 S3 110.3(6) . . ? C28 C26 S3 102.7(7) . . ? O6 C30 C18 122.7(5) . . ? O6 C30 S4 125.9(4) . . ? C18 C30 S4 111.4(3) . . ? C32 C31 C34 112.7(7) . . ? C32 C31 C33 110.4(7) . . ? C34 C31 C33 109.9(6) . . ? C32 C31 S4 109.5(5) . . ? C34 C31 S4 112.3(5) . . ? C33 C31 S4 101.5(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.462 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.068 # Attachment '12.cif' data_8372 _database_code_depnum_ccdc_archive 'CCDC 692930' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H36 O3 S2' _chemical_formula_weight 400.62 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' 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 Cc 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' _cell_length_a 18.8390(19) _cell_length_b 12.6378(14) _cell_length_c 10.2009(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.756(3) _cell_angle_gamma 90.00 _cell_volume 2416.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 914 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 18.19 _exptl_crystal_description ROD _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.101 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9199 _exptl_absorpt_correction_T_max 0.9906 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 area detector' _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 8416 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4012 _reflns_number_gt 2491 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0638P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(11) _refine_ls_number_reflns 4012 _refine_ls_number_parameters 242 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 S1 S 0.74230(8) 0.26383(9) 0.66245(12) 0.0655(4) Uani 1 1 d . . . S2 S 0.67835(6) 0.57355(9) 0.63414(9) 0.0553(3) Uani 1 1 d . . . O1 O 1.0204(2) 0.5968(4) 0.8649(5) 0.1132(16) Uani 1 1 d . . . O2 O 0.7965(2) 0.3415(3) 0.4548(3) 0.0772(11) Uani 1 1 d . . . O3 O 0.77624(15) 0.5855(2) 0.4651(3) 0.0587(8) Uani 1 1 d . . . C1 C 0.8007(2) 0.4590(3) 0.6397(4) 0.0442(10) Uani 1 1 d . . . H1 H 0.7852 0.4537 0.7294 0.053 Uiso 1 1 calc R . . C2 C 0.8805(2) 0.4819(3) 0.6497(4) 0.0472(10) Uani 1 1 d . . . H2 H 0.8939 0.5019 0.5617 0.057 Uiso 1 1 calc R . . C3 C 0.9043(2) 0.5696(4) 0.7484(4) 0.0553(12) Uani 1 1 d . . . H3 H 0.8764 0.5592 0.8246 0.066 Uiso 1 1 calc R . . C4 C 0.9799(3) 0.5421(5) 0.7962(5) 0.0740(16) Uani 1 1 d . . . C5 C 0.9967(3) 0.4330(4) 0.7470(7) 0.0836(18) Uani 1 1 d . . . H5A H 1.0269 0.4375 0.6745 0.100 Uiso 1 1 calc R . . H5B H 1.0212 0.3904 0.8180 0.100 Uiso 1 1 calc R . . C6 C 0.9253(2) 0.3857(4) 0.7006(5) 0.0673(14) Uani 1 1 d . . . H6A H 0.9042 0.3508 0.7732 0.081 Uiso 1 1 calc R . . H6B H 0.9296 0.3342 0.6300 0.081 Uiso 1 1 calc R . . C7 C 0.8939(3) 0.6852(4) 0.7077(5) 0.0674(14) Uani 1 1 d . . . H7A H 0.8430 0.6976 0.6830 0.081 Uiso 1 1 calc R . . H7B H 0.9086 0.7300 0.7840 0.081 Uiso 1 1 calc R . . C8 C 0.9344(3) 0.7188(4) 0.5954(6) 0.0805(16) Uani 1 1 d . . . H8A H 0.9256 0.6671 0.5240 0.097 Uiso 1 1 calc R . . H8B H 0.9855 0.7169 0.6250 0.097 Uiso 1 1 calc R . . C9 C 0.9159(4) 0.8281(5) 0.5408(9) 0.110(2) Uani 1 1 d . . . H9A H 0.9225 0.8797 0.6128 0.132 Uiso 1 1 calc R . . H9B H 0.8655 0.8292 0.5063 0.132 Uiso 1 1 calc R . . C10 C 0.9619(4) 0.8625(6) 0.4295(9) 0.116(3) Uani 1 1 d . . . H10A H 1.0108 0.8757 0.4681 0.139 Uiso 1 1 calc R . . H10B H 0.9633 0.8042 0.3664 0.139 Uiso 1 1 calc R . . C11 C 0.9352(4) 0.9563(8) 0.3597(9) 0.139(3) Uani 1 1 d . . . H11A H 0.8872 0.9433 0.3192 0.209 Uiso 1 1 calc R . . H11B H 0.9659 0.9737 0.2921 0.209 Uiso 1 1 calc R . . H11C H 0.9346 1.0149 0.4211 0.209 Uiso 1 1 calc R . . C12 C 0.7826(2) 0.3562(3) 0.5652(4) 0.0480(10) Uani 1 1 d . . . C13 C 0.7197(3) 0.1488(4) 0.5555(6) 0.0705(14) Uani 1 1 d . . . C14 C 0.7863(4) 0.0979(5) 0.5168(8) 0.119(3) Uani 1 1 d . . . H14A H 0.8156 0.0747 0.5952 0.179 Uiso 1 1 calc R . . H14B H 0.8128 0.1487 0.4695 0.179 Uiso 1 1 calc R . . H14C H 0.7738 0.0375 0.4605 0.179 Uiso 1 1 calc R . . C15 C 0.6829(6) 0.0752(6) 0.6474(10) 0.166(4) Uani 1 1 d . . . H15A H 0.6675 0.0113 0.6003 0.249 Uiso 1 1 calc R . . H15B H 0.6419 0.1109 0.6772 0.249 Uiso 1 1 calc R . . H15C H 0.7162 0.0571 0.7228 0.249 Uiso 1 1 calc R . . C16 C 0.6707(3) 0.1796(6) 0.4360(8) 0.114(2) Uani 1 1 d . . . H16A H 0.6961 0.2248 0.3796 0.171 Uiso 1 1 calc R . . H16B H 0.6299 0.2175 0.4634 0.171 Uiso 1 1 calc R . . H16C H 0.6545 0.1165 0.3879 0.171 Uiso 1 1 calc R . . C17 C 0.7571(2) 0.5448(3) 0.5627(4) 0.0462(10) Uani 1 1 d . . . C18 C 0.6294(2) 0.6714(4) 0.5249(4) 0.0560(12) Uani 1 1 d . . . C19 C 0.6105(3) 0.6259(4) 0.3886(5) 0.0644(13) Uani 1 1 d . . . H19A H 0.5799 0.6750 0.3363 0.097 Uiso 1 1 calc R . . H19B H 0.5857 0.5592 0.3956 0.097 Uiso 1 1 calc R . . H19C H 0.6538 0.6142 0.3466 0.097 Uiso 1 1 calc R . . C20 C 0.6721(3) 0.7719(4) 0.5198(5) 0.0752(15) Uani 1 1 d . . . H20A H 0.6458 0.8224 0.4621 0.113 Uiso 1 1 calc R . . H20B H 0.7173 0.7564 0.4864 0.113 Uiso 1 1 calc R . . H20C H 0.6806 0.8016 0.6077 0.113 Uiso 1 1 calc R . . C21 C 0.5623(3) 0.6885(5) 0.5943(6) 0.0842(18) Uani 1 1 d . . . H21A H 0.5754 0.7151 0.6826 0.126 Uiso 1 1 calc R . . H21B H 0.5371 0.6219 0.5991 0.126 Uiso 1 1 calc R . . H21C H 0.5316 0.7395 0.5452 0.126 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 S1 0.0966(10) 0.0460(7) 0.0581(8) -0.0012(6) 0.0282(6) -0.0073(7) S2 0.0559(7) 0.0599(7) 0.0531(7) 0.0090(6) 0.0200(5) 0.0133(6) O1 0.099(3) 0.110(4) 0.121(4) -0.023(3) -0.037(3) -0.022(3) O2 0.107(3) 0.076(2) 0.054(2) -0.0214(18) 0.0331(19) -0.0335(19) O3 0.0565(18) 0.070(2) 0.0517(19) 0.0186(16) 0.0172(14) 0.0108(15) C1 0.051(3) 0.045(2) 0.038(2) 0.0008(19) 0.0113(18) 0.0010(18) C2 0.049(3) 0.049(3) 0.044(2) -0.002(2) 0.0056(18) 0.0014(19) C3 0.067(3) 0.051(3) 0.048(3) -0.011(2) 0.004(2) -0.004(2) C4 0.072(4) 0.074(4) 0.072(4) -0.010(3) -0.013(3) -0.016(3) C5 0.067(4) 0.073(4) 0.106(5) -0.002(3) -0.014(3) 0.005(3) C6 0.061(3) 0.054(3) 0.085(4) 0.003(3) -0.006(3) 0.009(2) C7 0.081(4) 0.058(3) 0.063(3) -0.014(3) 0.008(3) -0.005(2) C8 0.094(4) 0.058(3) 0.093(4) 0.003(3) 0.024(3) -0.014(3) C9 0.108(5) 0.071(4) 0.154(7) 0.008(4) 0.024(4) -0.010(4) C10 0.136(6) 0.076(5) 0.137(7) 0.027(4) 0.027(5) -0.020(4) C11 0.127(7) 0.164(9) 0.126(7) 0.011(6) 0.008(5) -0.022(6) C12 0.043(2) 0.054(3) 0.048(3) -0.006(2) 0.0068(18) -0.0009(19) C13 0.086(4) 0.053(3) 0.073(3) -0.015(3) 0.014(3) -0.010(3) C14 0.118(6) 0.089(5) 0.147(7) -0.055(5) -0.014(5) 0.034(4) C15 0.278(11) 0.077(5) 0.160(8) -0.035(5) 0.100(7) -0.090(7) C16 0.089(5) 0.100(5) 0.145(6) -0.022(4) -0.026(4) -0.022(4) C17 0.050(2) 0.051(3) 0.039(2) -0.002(2) 0.010(2) -0.0031(18) C18 0.054(3) 0.055(3) 0.058(3) 0.001(2) 0.002(2) 0.011(2) C19 0.063(3) 0.072(3) 0.056(3) -0.006(2) 0.000(2) -0.003(2) C20 0.097(4) 0.055(3) 0.071(4) -0.004(3) -0.007(3) 0.013(3) C21 0.069(4) 0.099(4) 0.086(4) 0.009(3) 0.016(3) 0.038(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C12 1.753(5) . ? S1 C13 1.842(5) . ? S2 C17 1.756(4) . ? S2 C18 1.848(4) . ? O1 C4 1.202(6) . ? O2 C12 1.195(5) . ? O3 C17 1.207(5) . ? C1 C2 1.525(6) . ? C1 C12 1.527(6) . ? C1 C17 1.528(6) . ? C2 C3 1.533(6) . ? C2 C6 1.540(6) . ? C3 C4 1.499(7) . ? C3 C7 1.526(7) . ? C4 C5 1.512(8) . ? C5 C6 1.504(7) . ? C7 C8 1.500(8) . ? C8 C9 1.517(8) . ? C9 C10 1.557(11) . ? C10 C11 1.448(10) . ? C13 C14 1.499(8) . ? C13 C16 1.505(8) . ? C13 C15 1.533(9) . ? C18 C20 1.506(7) . ? C18 C19 1.514(6) . ? C18 C21 1.524(7) . ? 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 C12 S1 C13 106.1(2) . . ? C17 S2 C18 106.3(2) . . ? C2 C1 C12 111.4(3) . . ? C2 C1 C17 112.0(3) . . ? C12 C1 C17 105.5(3) . . ? C1 C2 C3 113.7(3) . . ? C1 C2 C6 112.1(4) . . ? C3 C2 C6 103.6(3) . . ? C4 C3 C7 113.7(4) . . ? C4 C3 C2 104.6(4) . . ? C7 C3 C2 119.5(4) . . ? O1 C4 C3 125.7(5) . . ? O1 C4 C5 125.2(5) . . ? C3 C4 C5 109.1(4) . . ? C6 C5 C4 104.9(4) . . ? C5 C6 C2 103.6(4) . . ? C8 C7 C3 114.7(5) . . ? C7 C8 C9 115.0(5) . . ? C8 C9 C10 113.4(6) . . ? C11 C10 C9 113.4(7) . . ? O2 C12 C1 122.8(4) . . ? O2 C12 S1 125.3(3) . . ? C1 C12 S1 111.9(3) . . ? C14 C13 C16 111.1(6) . . ? C14 C13 C15 110.0(7) . . ? C16 C13 C15 112.0(7) . . ? C14 C13 S1 110.1(4) . . ? C16 C13 S1 111.2(4) . . ? C15 C13 S1 102.0(4) . . ? O3 C17 C1 122.5(4) . . ? O3 C17 S2 126.1(3) . . ? C1 C17 S2 111.4(3) . . ? C20 C18 C19 111.5(4) . . ? C20 C18 C21 111.5(4) . . ? C19 C18 C21 110.5(4) . . ? C20 C18 S2 110.4(3) . . ? C19 C18 S2 110.9(3) . . ? C21 C18 S2 101.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.234 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.044 # Attachment '8.cif' data_8058a _database_code_depnum_ccdc_archive 'CCDC 692931' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H44 O3 S2' _chemical_formula_weight 564.81 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' 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 18.7796(12) _cell_length_b 13.0947(8) _cell_length_c 11.9738(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.651(2) _cell_angle_gamma 90.00 _cell_volume 2934.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2140 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 20.28 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9304 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _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 area detector' _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 19592 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6730 _reflns_number_gt 4206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0755P)^2^+0.0000P] 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 6730 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1132 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1418 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 S1 S 0.24287(4) 0.54501(6) 0.79207(6) 0.0480(2) Uani 1 1 d . . . S2 S 0.20937(4) 0.70076(5) 1.05552(6) 0.04022(19) Uani 1 1 d . . . O1 O 0.35331(13) 0.68311(18) 1.31396(17) 0.0681(7) Uani 1 1 d . . . O2 O 0.37354(11) 0.48293(16) 0.85725(17) 0.0572(6) Uani 1 1 d . . . O3 O 0.24979(11) 0.50804(15) 1.08210(17) 0.0525(5) Uani 1 1 d . . . C1 C 0.32631(13) 0.61045(18) 0.97655(19) 0.0318(5) Uani 1 1 d . . . H1 H 0.3219 0.6800 0.9466 0.038 Uiso 1 1 calc R . . C2 C 0.39873(13) 0.60305(17) 1.0481(2) 0.0331(6) Uani 1 1 d . . . H2 H 0.4370 0.6087 0.9976 0.040 Uiso 1 1 calc R . . C3 C 0.41106(14) 0.68591(18) 1.1395(2) 0.0365(6) Uani 1 1 d . . . C4 C 0.37935(15) 0.6383(2) 1.2400(2) 0.0458(7) Uani 1 1 d . . . C5 C 0.38644(18) 0.5238(2) 1.2323(2) 0.0527(8) Uani 1 1 d . . . H5A H 0.3411 0.4909 1.2421 0.063 Uiso 1 1 calc R . . H5B H 0.4217 0.4988 1.2894 0.063 Uiso 1 1 calc R . . C6 C 0.41003(16) 0.5024(2) 1.1153(2) 0.0459(7) Uani 1 1 d . . . H6A H 0.3816 0.4479 1.0796 0.055 Uiso 1 1 calc R . . H6B H 0.4599 0.4824 1.1198 0.055 Uiso 1 1 calc R . . C7 C 0.49444(15) 0.6980(2) 1.1768(3) 0.0502(7) Uani 1 1 d . . . H7 H 0.5173 0.6398 1.2168 0.060 Uiso 1 1 calc R . . C8 C 0.52836(17) 0.7330(3) 1.0758(3) 0.0625(9) Uani 1 1 d . . . H8 H 0.5588 0.6947 1.0348 0.075 Uiso 1 1 calc R . . C9 C 0.50794(18) 0.8273(3) 1.0544(3) 0.0657(9) Uani 1 1 d . . . H9 H 0.5211 0.8676 0.9955 0.079 Uiso 1 1 calc R . . C10 C 0.45943(17) 0.8582(2) 1.1425(3) 0.0613(9) Uani 1 1 d . . . H10 H 0.4541 0.9318 1.1541 0.074 Uiso 1 1 calc R . . C11 C 0.49348(17) 0.7979(2) 1.2425(3) 0.0593(9) Uani 1 1 d . . . H11A H 0.5409 0.8221 1.2678 0.071 Uiso 1 1 calc R . . H11B H 0.4635 0.7948 1.3047 0.071 Uiso 1 1 calc R . . C12 C 0.38903(15) 0.79755(19) 1.1144(2) 0.0450(7) Uani 1 1 d . . . H12A H 0.3521 0.8194 1.1612 0.054 Uiso 1 1 calc R . . H12B H 0.3719 0.8061 1.0363 0.054 Uiso 1 1 calc R . . C13 C 0.32455(15) 0.53661(19) 0.8766(2) 0.0385(6) Uani 1 1 d . . . C14 C 0.24355(14) 0.44113(18) 0.6882(2) 0.0345(6) Uani 1 1 d . . . C15 C 0.29972(16) 0.4560(2) 0.6056(2) 0.0488(7) Uani 1 1 d . . . H15A H 0.3470 0.4531 0.6445 0.059 Uiso 1 1 calc R . . H15B H 0.2938 0.5224 0.5701 0.059 Uiso 1 1 calc R . . C16 C 0.29188(17) 0.3716(2) 0.5163(2) 0.0543(8) Uani 1 1 d . . . H16 H 0.3286 0.3803 0.4634 0.065 Uiso 1 1 calc R . . C17 C 0.30079(18) 0.2683(2) 0.5728(3) 0.0601(9) Uani 1 1 d . . . H17A H 0.2968 0.2147 0.5167 0.072 Uiso 1 1 calc R . . H17B H 0.3477 0.2637 0.6127 0.072 Uiso 1 1 calc R . . C18 C 0.24377(19) 0.2542(2) 0.6540(3) 0.0578(9) Uani 1 1 d . . . H18 H 0.2496 0.1871 0.6897 0.069 Uiso 1 1 calc R . . C19 C 0.25163(17) 0.3371(2) 0.7438(2) 0.0487(7) Uani 1 1 d . . . H19A H 0.2154 0.3284 0.7963 0.058 Uiso 1 1 calc R . . H19B H 0.2982 0.3319 0.7850 0.058 Uiso 1 1 calc R . . C20 C 0.21825(19) 0.3794(2) 0.4541(2) 0.0632(9) Uani 1 1 d . . . H20A H 0.2125 0.4459 0.4188 0.076 Uiso 1 1 calc R . . H20B H 0.2131 0.3277 0.3960 0.076 Uiso 1 1 calc R . . C21 C 0.16156(17) 0.3644(2) 0.5361(3) 0.0594(9) Uani 1 1 d . . . H21 H 0.1141 0.3688 0.4958 0.071 Uiso 1 1 calc R . . C22 C 0.16913(15) 0.4488(2) 0.6251(2) 0.0512(8) Uani 1 1 d . . . H22A H 0.1325 0.4410 0.6772 0.061 Uiso 1 1 calc R . . H22B H 0.1632 0.5152 0.5897 0.061 Uiso 1 1 calc R . . C23 C 0.1703(2) 0.2606(3) 0.5918(3) 0.0728(10) Uani 1 1 d . . . H23A H 0.1338 0.2510 0.6437 0.087 Uiso 1 1 calc R . . H23B H 0.1650 0.2072 0.5355 0.087 Uiso 1 1 calc R . . C25 C 0.26174(13) 0.59032(19) 1.0433(2) 0.0346(6) Uani 1 1 d . . . C26 C 0.13540(13) 0.66259(19) 1.1377(2) 0.0355(6) Uani 1 1 d . . . C27 C 0.09293(16) 0.5734(2) 1.0839(2) 0.0518(8) Uani 1 1 d . . . H27A H 0.1231 0.5133 1.0829 0.062 Uiso 1 1 calc R . . H27B H 0.0765 0.5903 1.0072 0.062 Uiso 1 1 calc R . . C28 C 0.02893(17) 0.5518(3) 1.1514(3) 0.0640(9) Uani 1 1 d . . . H28 H 0.0019 0.4938 1.1182 0.077 Uiso 1 1 calc R . . C29 C -0.01902(17) 0.6461(3) 1.1478(3) 0.0740(11) Uani 1 1 d . . . H29A H -0.0347 0.6625 1.0707 0.089 Uiso 1 1 calc R . . H29B H -0.0609 0.6327 1.1878 0.089 Uiso 1 1 calc R . . C30 C 0.02242(16) 0.7350(3) 1.2015(3) 0.0600(9) Uani 1 1 d . . . H30 H -0.0084 0.7954 1.1998 0.072 Uiso 1 1 calc R . . C31 C 0.08750(16) 0.7576(2) 1.1368(3) 0.0516(7) Uani 1 1 d . . . H31A H 0.1141 0.8146 1.1712 0.062 Uiso 1 1 calc R . . H31B H 0.0721 0.7761 1.0602 0.062 Uiso 1 1 calc R . . C32 C 0.05499(18) 0.5263(3) 1.2721(3) 0.0655(9) Uani 1 1 d . . . H32A H 0.0145 0.5108 1.3147 0.079 Uiso 1 1 calc R . . H32B H 0.0858 0.4668 1.2737 0.079 Uiso 1 1 calc R . . C33 C 0.09573(17) 0.6167(3) 1.3239(2) 0.0579(8) Uani 1 1 d . . . H33 H 0.1118 0.6006 1.4018 0.069 Uiso 1 1 calc R . . C34 C 0.16134(14) 0.6382(2) 1.2585(2) 0.0448(7) Uani 1 1 d . . . H34A H 0.1881 0.6955 1.2917 0.054 Uiso 1 1 calc R . . H34B H 0.1924 0.5790 1.2610 0.054 Uiso 1 1 calc R . . C35 C 0.04736(18) 0.7103(3) 1.3217(3) 0.0647(9) Uani 1 1 d . . . H35A H 0.0065 0.6967 1.3640 0.078 Uiso 1 1 calc R . . H35B H 0.0733 0.7679 1.3558 0.078 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 S1 0.0514(5) 0.0498(4) 0.0411(4) -0.0168(3) -0.0075(3) 0.0131(3) S2 0.0422(4) 0.0357(4) 0.0441(4) 0.0001(3) 0.0122(3) 0.0031(3) O1 0.0836(17) 0.0795(16) 0.0428(13) -0.0189(11) 0.0160(11) 0.0121(13) O2 0.0489(13) 0.0715(14) 0.0500(13) -0.0285(11) -0.0029(9) 0.0171(11) O3 0.0554(13) 0.0397(11) 0.0648(14) 0.0138(10) 0.0185(10) 0.0043(9) C1 0.0373(14) 0.0294(13) 0.0291(14) -0.0029(10) 0.0047(10) 0.0030(10) C2 0.0351(14) 0.0309(13) 0.0335(14) -0.0044(10) 0.0040(10) 0.0041(10) C3 0.0372(15) 0.0351(14) 0.0364(15) -0.0112(11) -0.0014(11) 0.0048(11) C4 0.0460(17) 0.0557(18) 0.0343(16) -0.0088(13) -0.0049(12) 0.0075(13) C5 0.066(2) 0.0504(18) 0.0402(18) 0.0067(13) -0.0023(14) 0.0088(14) C6 0.0566(19) 0.0362(15) 0.0440(17) -0.0043(12) -0.0013(13) 0.0078(13) C7 0.0445(18) 0.0430(16) 0.061(2) -0.0103(14) -0.0064(14) 0.0084(13) C8 0.0435(19) 0.065(2) 0.079(3) -0.0141(18) 0.0056(16) -0.0042(16) C9 0.055(2) 0.062(2) 0.080(3) 0.0025(18) 0.0075(17) -0.0094(17) C10 0.051(2) 0.0344(15) 0.098(3) -0.0121(16) 0.0022(17) 0.0000(13) C11 0.052(2) 0.0595(19) 0.063(2) -0.0248(16) -0.0137(15) -0.0008(15) C12 0.0464(17) 0.0366(14) 0.0511(18) -0.0120(13) -0.0009(12) 0.0035(12) C13 0.0440(16) 0.0383(14) 0.0329(15) -0.0041(11) 0.0009(11) 0.0004(12) C14 0.0425(15) 0.0345(13) 0.0262(14) -0.0060(10) 0.0018(10) 0.0006(11) C15 0.058(2) 0.0482(17) 0.0413(17) -0.0033(13) 0.0106(13) -0.0086(14) C16 0.065(2) 0.062(2) 0.0378(17) -0.0114(14) 0.0154(14) 0.0025(16) C17 0.073(2) 0.0543(19) 0.051(2) -0.0200(15) -0.0063(16) 0.0233(16) C18 0.090(3) 0.0321(15) 0.051(2) -0.0002(13) 0.0026(17) 0.0011(15) C19 0.072(2) 0.0392(15) 0.0350(16) 0.0028(12) 0.0053(13) -0.0042(14) C20 0.094(3) 0.062(2) 0.0321(17) -0.0129(14) -0.0083(16) 0.0142(18) C21 0.055(2) 0.065(2) 0.055(2) -0.0230(16) -0.0154(15) 0.0045(16) C22 0.0470(18) 0.0591(19) 0.0458(18) -0.0133(14) -0.0055(13) 0.0077(14) C23 0.077(3) 0.063(2) 0.079(3) -0.0188(19) 0.0035(19) -0.0226(19) C25 0.0379(15) 0.0352(14) 0.0305(14) -0.0030(11) 0.0011(10) 0.0031(11) C26 0.0350(14) 0.0410(14) 0.0308(14) -0.0028(11) 0.0056(10) -0.0016(11) C27 0.0476(18) 0.0648(19) 0.0428(18) -0.0123(14) 0.0025(13) -0.0129(14) C28 0.050(2) 0.084(2) 0.058(2) -0.0094(17) 0.0019(15) -0.0291(18) C29 0.0378(19) 0.128(3) 0.057(2) 0.012(2) 0.0037(14) -0.005(2) C30 0.0438(19) 0.078(2) 0.060(2) 0.0092(17) 0.0171(15) 0.0213(16) C31 0.0521(19) 0.0581(18) 0.0458(18) 0.0052(14) 0.0112(13) 0.0120(15) C32 0.059(2) 0.075(2) 0.065(2) 0.0120(18) 0.0183(16) -0.0094(17) C33 0.056(2) 0.085(2) 0.0327(17) 0.0090(15) 0.0026(13) 0.0018(17) C34 0.0417(17) 0.0589(18) 0.0332(15) -0.0028(13) -0.0008(11) 0.0009(13) C35 0.057(2) 0.094(3) 0.045(2) -0.0121(17) 0.0170(14) 0.0060(18) _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 S1 C13 1.771(3) . ? S1 C14 1.844(2) . ? S2 C25 1.762(3) . ? S2 C26 1.836(3) . ? O1 C4 1.200(3) . ? O2 C13 1.195(3) . ? O3 C25 1.202(3) . ? C1 C25 1.528(3) . ? C1 C13 1.537(3) . ? C1 C2 1.551(3) . ? C2 C3 1.545(3) . ? C2 C6 1.550(3) . ? C3 C4 1.519(4) . ? C3 C12 1.542(3) . ? C3 C7 1.601(4) . ? C4 C5 1.508(4) . ? C5 C6 1.529(4) . ? C7 C8 1.484(5) . ? C7 C11 1.527(4) . ? C8 C9 1.312(5) . ? C9 C10 1.505(5) . ? C10 C11 1.530(5) . ? C10 C12 1.556(4) . ? C14 C15 1.516(4) . ? C14 C19 1.519(3) . ? C14 C22 1.537(4) . ? C15 C16 1.535(4) . ? C16 C17 1.516(4) . ? C16 C20 1.520(4) . ? C17 C18 1.515(5) . ? C18 C23 1.516(5) . ? C18 C19 1.527(4) . ? C20 C21 1.519(5) . ? C21 C23 1.518(5) . ? C21 C22 1.533(4) . ? C26 C34 1.521(4) . ? C26 C27 1.527(4) . ? C26 C31 1.535(4) . ? C27 C28 1.529(4) . ? C28 C32 1.524(4) . ? C28 C29 1.527(5) . ? C29 C30 1.515(5) . ? C30 C35 1.512(4) . ? C30 C31 1.528(4) . ? C32 C33 1.515(4) . ? C33 C35 1.524(4) . ? C33 C34 1.539(4) . ? 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 C13 S1 C14 106.65(12) . . ? C25 S2 C26 105.83(12) . . ? C25 C1 C13 109.3(2) . . ? C25 C1 C2 113.4(2) . . ? C13 C1 C2 110.7(2) . . ? C3 C2 C6 102.90(19) . . ? C3 C2 C1 114.95(19) . . ? C6 C2 C1 114.7(2) . . ? C4 C3 C12 115.3(2) . . ? C4 C3 C2 103.1(2) . . ? C12 C3 C2 120.3(2) . . ? C4 C3 C7 104.9(2) . . ? C12 C3 C7 101.6(2) . . ? C2 C3 C7 110.7(2) . . ? O1 C4 C5 125.1(3) . . ? O1 C4 C3 126.4(3) . . ? C5 C4 C3 108.5(2) . . ? C4 C5 C6 105.8(2) . . ? C5 C6 C2 106.4(2) . . ? C8 C7 C11 100.3(3) . . ? C8 C7 C3 106.1(2) . . ? C11 C7 C3 100.2(2) . . ? C9 C8 C7 108.2(3) . . ? C8 C9 C10 107.5(3) . . ? C9 C10 C11 99.9(3) . . ? C9 C10 C12 105.2(3) . . ? C11 C10 C12 101.5(2) . . ? C7 C11 C10 93.5(2) . . ? C3 C12 C10 103.4(2) . . ? O2 C13 C1 123.5(2) . . ? O2 C13 S1 124.8(2) . . ? C1 C13 S1 111.64(18) . . ? C15 C14 C19 110.6(2) . . ? C15 C14 C22 108.9(2) . . ? C19 C14 C22 109.2(2) . . ? C15 C14 S1 112.87(18) . . ? C19 C14 S1 111.80(17) . . ? C22 C14 S1 103.14(17) . . ? C14 C15 C16 109.2(2) . . ? C17 C16 C20 110.0(3) . . ? C17 C16 C15 109.3(2) . . ? C20 C16 C15 109.0(2) . . ? C18 C17 C16 109.7(2) . . ? C17 C18 C23 109.9(3) . . ? C17 C18 C19 109.4(3) . . ? C23 C18 C19 109.8(3) . . ? C14 C19 C18 109.2(2) . . ? C21 C20 C16 109.4(2) . . ? C23 C21 C20 110.1(3) . . ? C23 C21 C22 109.9(3) . . ? C20 C21 C22 109.0(3) . . ? C21 C22 C14 108.9(2) . . ? C18 C23 C21 109.1(3) . . ? O3 C25 C1 122.5(2) . . ? O3 C25 S2 125.5(2) . . ? C1 C25 S2 111.94(18) . . ? C34 C26 C27 110.9(2) . . ? C34 C26 C31 108.6(2) . . ? C27 C26 C31 109.3(2) . . ? C34 C26 S2 111.63(18) . . ? C27 C26 S2 111.93(18) . . ? C31 C26 S2 104.11(18) . . ? C26 C27 C28 108.9(2) . . ? C32 C28 C29 110.3(3) . . ? C32 C28 C27 109.7(3) . . ? C29 C28 C27 108.8(3) . . ? C30 C29 C28 109.2(3) . . ? C35 C30 C29 110.4(3) . . ? C35 C30 C31 109.0(3) . . ? C29 C30 C31 109.8(3) . . ? C30 C31 C26 109.4(2) . . ? C33 C32 C28 109.3(3) . . ? C32 C33 C35 109.9(3) . . ? C32 C33 C34 109.5(3) . . ? C35 C33 C34 110.2(3) . . ? C26 C34 C33 108.3(2) . . ? C30 C35 C33 109.1(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.411 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.056 # Attachment 'ref21.cif' data_6373 _database_code_depnum_ccdc_archive 'CCDC 692932' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H41 Br Cl2 N2 O3 S' _chemical_formula_weight 612.48 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1010(7) _cell_length_b 12.7221(10) _cell_length_c 28.619(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2949.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3322 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 21.22 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 1.675 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.4649 _exptl_absorpt_correction_T_max 0.9062 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 area detector' _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 20732 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6762 _reflns_number_gt 5181 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. The flack value indicates that the absolute structure reported is correct. ; _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^)+(0.0751P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(11) _chemical_absolute_configuration rmad _refine_ls_number_reflns 6762 _refine_ls_number_parameters 329 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1549 _refine_ls_wR_factor_gt 0.1430 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.023 _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 0.18182(6) 0.30280(4) 0.247701(18) 0.05269(18) Uani 1 1 d . . . S1 S 0.42744(12) 0.44765(8) 0.12892(3) 0.0273(2) Uani 1 1 d . . . O1 O 0.2518(5) 0.7790(3) 0.09208(13) 0.0564(10) Uani 1 1 d . . . O2 O 0.5102(3) 0.5459(2) 0.12367(11) 0.0342(7) Uani 1 1 d . . . O3 O 0.5122(4) 0.3638(2) 0.15186(11) 0.0371(7) Uani 1 1 d . . . N1 N 0.3344(4) 0.6752(3) 0.22282(11) 0.0300(7) Uani 1 1 d . . . N2 N 0.2628(4) 0.4684(2) 0.15939(11) 0.0262(7) Uani 1 1 d D . . C1 C 0.2160(6) 0.8372(4) 0.1231(2) 0.0464(12) Uani 1 1 d . . . C2 C 0.0981(8) 0.9301(4) 0.1205(3) 0.0726(19) Uani 1 1 d . . . H2A H 0.1385 0.9826 0.0982 0.087 Uiso 1 1 calc R . . H2B H -0.0119 0.9070 0.1107 0.087 Uiso 1 1 calc R . . C3 C 0.0918(9) 0.9760(5) 0.1693(3) 0.079(2) Uani 1 1 d . . . H3A H 0.1255 1.0500 0.1692 0.095 Uiso 1 1 calc R . . H3B H -0.0196 0.9706 0.1824 0.095 Uiso 1 1 calc R . . C4 C 0.2114(8) 0.9104(4) 0.1966(2) 0.0604(16) Uani 1 1 d . . . H4 H 0.2378 0.9231 0.2281 0.073 Uiso 1 1 calc R . . C5 C 0.2775(5) 0.8312(3) 0.17146(17) 0.0388(10) Uani 1 1 d . . . C6 C 0.3989(5) 0.7501(3) 0.18665(15) 0.0319(9) Uani 1 1 d . . . H6A H 0.4966 0.7856 0.1992 0.038 Uiso 1 1 calc R . . H6B H 0.4340 0.7097 0.1592 0.038 Uiso 1 1 calc R . . C7 C 0.2998(6) 0.7309(4) 0.26879(15) 0.0410(11) Uani 1 1 d . . . H7A H 0.3816 0.7862 0.2745 0.049 Uiso 1 1 calc R . . H7B H 0.1895 0.7625 0.2686 0.049 Uiso 1 1 calc R . . C8 C 0.3113(7) 0.6466(4) 0.30547(16) 0.0503(13) Uani 1 1 d . . . H8A H 0.2028 0.6148 0.3110 0.060 Uiso 1 1 calc R . . H8B H 0.3522 0.6758 0.3350 0.060 Uiso 1 1 calc R . . C9 C 0.4306(10) 0.5656(5) 0.2866(2) 0.0703(18) Uani 1 1 d . . . H9A H 0.5314 0.5640 0.3055 0.084 Uiso 1 1 calc R . . H9B H 0.3804 0.4956 0.2870 0.084 Uiso 1 1 calc R . . C10 C 0.4689(5) 0.5981(4) 0.23774(16) 0.0395(11) Uani 1 1 d . . . H10A H 0.4696 0.5367 0.2171 0.047 Uiso 1 1 calc R . . H10B H 0.5775 0.6319 0.2363 0.047 Uiso 1 1 calc R . . C11 C 0.1762(5) 0.6196(3) 0.20771(13) 0.0268(8) Uani 1 1 d . . . H11A H 0.0862 0.6709 0.2091 0.032 Uiso 1 1 calc R . . H11B H 0.1520 0.5651 0.2310 0.032 Uiso 1 1 calc R . . C12 C 0.1712(4) 0.5676(3) 0.15915(13) 0.0241(7) Uani 1 1 d . . . H12 H 0.2239 0.6157 0.1364 0.029 Uiso 1 1 calc R . . C13 C -0.0139(4) 0.5521(3) 0.14462(15) 0.0294(9) Uani 1 1 d . . . C14 C -0.1115(6) 0.4975(4) 0.18351(18) 0.0442(12) Uani 1 1 d . . . H14A H -0.1217 0.5445 0.2100 0.066 Uiso 1 1 calc R . . H14B H -0.0540 0.4341 0.1930 0.066 Uiso 1 1 calc R . . H14C H -0.2205 0.4793 0.1721 0.066 Uiso 1 1 calc R . . C15 C -0.0195(6) 0.4851(4) 0.10066(19) 0.0511(14) Uani 1 1 d . . . H15A H 0.0349 0.4184 0.1065 0.077 Uiso 1 1 calc R . . H15B H 0.0367 0.5215 0.0755 0.077 Uiso 1 1 calc R . . H15C H -0.1335 0.4726 0.0919 0.077 Uiso 1 1 calc R . . C16 C -0.0937(5) 0.6575(3) 0.13334(17) 0.0368(10) Uani 1 1 d . . . H16A H -0.2078 0.6465 0.1243 0.055 Uiso 1 1 calc R . . H16B H -0.0345 0.6907 0.1078 0.055 Uiso 1 1 calc R . . H16C H -0.0894 0.7024 0.1607 0.055 Uiso 1 1 calc R . . C17 C 0.3704(5) 0.4014(3) 0.07195(14) 0.0283(9) Uani 1 1 d . . . C18 C 0.4082(5) 0.4607(3) 0.03209(14) 0.0330(9) Uani 1 1 d . . . C19 C 0.3666(6) 0.4160(4) -0.01120(16) 0.0405(11) Uani 1 1 d . . . H19 H 0.3906 0.4541 -0.0385 0.049 Uiso 1 1 calc R . . C20 C 0.2931(6) 0.3198(4) -0.01562(16) 0.0417(11) Uani 1 1 d . . . C21 C 0.2559(6) 0.2650(4) 0.02528(18) 0.0426(11) Uani 1 1 d . . . H21 H 0.2016 0.1999 0.0228 0.051 Uiso 1 1 calc R . . C22 C 0.2951(5) 0.3019(3) 0.06876(15) 0.0347(9) Uani 1 1 d . . . C23 C 0.4833(7) 0.5704(4) 0.03028(19) 0.0532(14) Uani 1 1 d . . . H23A H 0.4226 0.6168 0.0510 0.080 Uiso 1 1 calc R . . H23B H 0.4774 0.5972 -0.0014 0.080 Uiso 1 1 calc R . . H23C H 0.5978 0.5672 0.0401 0.080 Uiso 1 1 calc R . . C24 C 0.2518(9) 0.2748(5) -0.0628(2) 0.0673(17) Uani 1 1 d . . . H24A H 0.1370 0.2892 -0.0700 0.101 Uiso 1 1 calc R . . H24B H 0.2698 0.1994 -0.0624 0.101 Uiso 1 1 calc R . . H24C H 0.3219 0.3067 -0.0863 0.101 Uiso 1 1 calc R . . C25 C 0.2516(7) 0.2355(4) 0.10967(17) 0.0453(12) Uani 1 1 d . . . H25A H 0.1699 0.1837 0.1005 0.068 Uiso 1 1 calc R . . H25B H 0.2068 0.2795 0.1343 0.068 Uiso 1 1 calc R . . H25C H 0.3498 0.2000 0.1210 0.068 Uiso 1 1 calc R . . Cl1A Cl 0.4330(3) 1.00553(19) 0.03286(10) 0.1192(8) Uani 1 1 d D . . C1S C 0.5486(16) 0.8935(8) 0.0413(3) 0.091(3) Uiso 0.709(8) 1 d PD A 1 H1S1 H 0.6362 0.8890 0.0178 0.110 Uiso 0.709(8) 1 calc PR A 1 H1S2 H 0.4785 0.8310 0.0386 0.110 Uiso 0.709(8) 1 calc PR A 1 Cl1B Cl 0.6345(4) 0.9005(5) 0.09756(16) 0.140(3) Uani 0.709(8) 1 d PD A 1 C2S C 0.520(3) 0.8791(13) 0.0229(7) 0.086(8) Uiso 0.291(8) 1 d PD A 2 H2S1 H 0.4295 0.8285 0.0208 0.104 Uiso 0.291(8) 1 calc PR A 2 H2S2 H 0.5748 0.8805 -0.0076 0.104 Uiso 0.291(8) 1 calc PR A 2 Cl2B Cl 0.6638(11) 0.8304(7) 0.0641(4) 0.107(3) Uiso 0.291(8) 1 d PD A 2 H1N H 0.254(6) 0.420(2) 0.1814(11) 0.032 Uiso 1 1 d 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 0.0382(3) 0.0634(3) 0.0565(3) 0.0290(3) 0.0070(3) 0.0098(2) S1 0.0209(4) 0.0323(5) 0.0286(5) -0.0029(4) -0.0023(4) 0.0017(4) O1 0.072(3) 0.052(2) 0.045(2) 0.0084(18) -0.0072(19) -0.013(2) O2 0.0227(13) 0.0445(16) 0.0355(16) -0.0065(14) 0.0018(12) -0.0057(13) O3 0.0326(16) 0.0426(16) 0.0361(17) -0.0017(14) -0.0038(13) 0.0106(14) N1 0.0257(17) 0.0351(18) 0.0292(17) -0.0051(15) -0.0039(15) -0.0047(15) N2 0.0233(15) 0.0270(17) 0.0284(17) 0.0011(14) 0.0016(14) -0.0014(13) C1 0.036(3) 0.040(2) 0.063(3) 0.021(3) -0.002(2) -0.008(2) C2 0.058(4) 0.053(3) 0.107(6) 0.031(4) -0.010(4) 0.005(3) C3 0.074(4) 0.052(3) 0.111(6) 0.031(4) 0.046(4) 0.018(3) C4 0.066(4) 0.046(3) 0.069(4) 0.008(3) 0.027(3) 0.007(3) C5 0.031(2) 0.035(2) 0.050(3) 0.005(2) 0.005(2) -0.0041(18) C6 0.029(2) 0.031(2) 0.036(2) -0.0046(18) 0.0028(18) -0.0055(17) C7 0.042(3) 0.047(2) 0.034(2) -0.016(2) -0.002(2) -0.003(2) C8 0.059(3) 0.055(3) 0.037(2) -0.006(2) 0.001(3) -0.019(3) C9 0.093(5) 0.071(4) 0.047(3) 0.002(3) -0.015(3) 0.034(4) C10 0.031(2) 0.048(2) 0.040(3) -0.001(2) -0.0161(19) 0.002(2) C11 0.0191(17) 0.0310(19) 0.0303(19) -0.0014(16) -0.0028(17) -0.0014(17) C12 0.0183(16) 0.0264(18) 0.0277(18) -0.0013(15) 0.0000(16) -0.0017(15) C13 0.0190(18) 0.035(2) 0.035(2) -0.0005(18) -0.0026(15) -0.0001(17) C14 0.027(2) 0.048(3) 0.058(3) 0.015(2) -0.007(2) -0.010(2) C15 0.032(2) 0.064(3) 0.058(3) -0.026(3) -0.024(2) 0.010(2) C16 0.027(2) 0.039(2) 0.045(2) 0.002(2) -0.007(2) 0.0043(19) C17 0.0250(19) 0.033(2) 0.027(2) -0.0069(17) -0.0036(15) 0.0022(17) C18 0.031(2) 0.036(2) 0.033(2) -0.0002(18) -0.0004(18) 0.0015(19) C19 0.040(2) 0.050(3) 0.032(2) 0.000(2) 0.0010(19) 0.004(2) C20 0.042(2) 0.048(3) 0.036(2) -0.007(2) 0.001(2) 0.008(2) C21 0.034(2) 0.037(2) 0.057(3) -0.010(2) -0.007(2) -0.003(2) C22 0.037(2) 0.031(2) 0.037(2) -0.0088(18) -0.0006(18) 0.002(2) C23 0.074(4) 0.049(3) 0.036(3) 0.006(2) 0.002(2) -0.012(3) C24 0.070(4) 0.080(4) 0.051(3) -0.029(3) -0.011(3) 0.005(3) C25 0.051(3) 0.033(2) 0.052(3) 0.002(2) 0.001(2) -0.007(2) Cl1A 0.0993(16) 0.1166(17) 0.142(2) 0.0311(16) 0.0176(16) 0.0006(15) Cl1B 0.072(2) 0.221(6) 0.126(4) 0.077(4) -0.0112(19) -0.051(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.427(3) . ? S1 O3 1.429(3) . ? S1 N2 1.615(3) . ? S1 C17 1.794(4) . ? O1 C1 1.191(6) . ? N1 C6 1.501(5) . ? N1 C7 1.521(5) . ? N1 C11 1.526(5) . ? N1 C10 1.527(5) . ? N2 C12 1.464(5) . ? C1 C5 1.474(7) . ? C1 C2 1.522(7) . ? C2 C3 1.515(10) . ? C3 C4 1.498(9) . ? C4 C5 1.349(7) . ? C5 C6 1.490(6) . ? C7 C8 1.504(7) . ? C8 C9 1.512(8) . ? C9 C10 1.490(8) . ? C11 C12 1.540(5) . ? C12 C13 1.569(5) . ? C13 C15 1.520(6) . ? C13 C16 1.523(5) . ? C13 C14 1.532(6) . ? C17 C18 1.401(6) . ? C17 C22 1.408(6) . ? C18 C19 1.404(6) . ? C18 C23 1.524(6) . ? C19 C20 1.366(7) . ? C20 C21 1.396(7) . ? C20 C24 1.504(7) . ? C21 C22 1.367(6) . ? C22 C25 1.486(6) . ? Cl1A C1S 1.722(8) . ? Cl1A C2S 1.780(10) . ? C1S Cl1B 1.755(8) . ? C2S Cl2B 1.766(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 O2 S1 O3 118.50(17) . . ? O2 S1 N2 107.54(17) . . ? O3 S1 N2 105.72(18) . . ? O2 S1 C17 108.23(19) . . ? O3 S1 C17 107.25(19) . . ? N2 S1 C17 109.36(18) . . ? C6 N1 C7 111.4(3) . . ? C6 N1 C11 113.0(3) . . ? C7 N1 C11 107.8(3) . . ? C6 N1 C10 110.6(3) . . ? C7 N1 C10 100.9(3) . . ? C11 N1 C10 112.4(3) . . ? C12 N2 S1 123.9(3) . . ? O1 C1 C5 125.8(4) . . ? O1 C1 C2 126.9(5) . . ? C5 C1 C2 107.3(5) . . ? C3 C2 C1 106.0(5) . . ? C4 C3 C2 104.1(5) . . ? C5 C4 C3 113.3(6) . . ? C4 C5 C1 109.2(5) . . ? C4 C5 C6 128.6(5) . . ? C1 C5 C6 122.2(4) . . ? C5 C6 N1 114.3(3) . . ? C8 C7 N1 105.0(4) . . ? C7 C8 C9 106.0(4) . . ? C10 C9 C8 106.2(4) . . ? C9 C10 N1 107.0(4) . . ? N1 C11 C12 118.5(3) . . ? N2 C12 C11 110.6(3) . . ? N2 C12 C13 112.2(3) . . ? C11 C12 C13 108.6(3) . . ? C15 C13 C16 107.8(4) . . ? C15 C13 C14 109.4(4) . . ? C16 C13 C14 109.5(3) . . ? C15 C13 C12 108.5(3) . . ? C16 C13 C12 110.5(3) . . ? C14 C13 C12 111.0(3) . . ? C18 C17 C22 121.7(4) . . ? C18 C17 S1 120.5(3) . . ? C22 C17 S1 117.7(3) . . ? C17 C18 C19 116.6(4) . . ? C17 C18 C23 127.5(4) . . ? C19 C18 C23 115.9(4) . . ? C20 C19 C18 123.3(4) . . ? C19 C20 C21 117.7(4) . . ? C19 C20 C24 121.4(5) . . ? C21 C20 C24 120.9(5) . . ? C22 C21 C20 122.8(4) . . ? C21 C22 C17 117.9(4) . . ? C21 C22 C25 117.8(4) . . ? C17 C22 C25 124.2(4) . . ? C1S Cl1A C2S 19.7(5) . . ? Cl1A C1S Cl1B 107.6(5) . . ? Cl2B C2S Cl1A 118.2(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.699 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.089