# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Gareth J. Rowlands' 'Peter B. Hitchcock' 'Richard Seacome' _publ_contact_author_name 'Gareth J. Rowlands' _publ_contact_author_address ; Chemistry University of Sussex Falmer Brighton Sussex BN1 9QJ UNITED KINGDOM ; _publ_contact_author_email G.ROWLANDS@SUSSEX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; The synthesis and directed ortho-lithiation of 4-t-butylsulfinyl[2.2]paracyclophane ; _publ_requested_category FO data_jun2504 _database_code_depnum_ccdc_archive 'CCDC 278337' _audit_creation_date 2004-06-23T13:25:51-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H24 O1 S1' _chemical_formula_sum 'C20 H24 O1 S1' _chemical_formula_weight 312.45 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.9320(5) _cell_length_b 11.5642(6) _cell_length_c 14.7502(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1694.14(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6688 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.65779E-1 _diffrn_orient_matrix_ub_12 0.144074E-1 _diffrn_orient_matrix_ub_13 -0.500687E-1 _diffrn_orient_matrix_ub_21 -0.744329E-1 _diffrn_orient_matrix_ub_22 0.60521E-2 _diffrn_orient_matrix_ub_23 0.454072E-1 _diffrn_orient_matrix_ub_31 0.164395E-1 _diffrn_orient_matrix_ub_32 0.850501E-1 _diffrn_orient_matrix_ub_33 0.52504E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_unetI/netI 0.0458 _diffrn_reflns_number 12874 _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 16 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 25.07 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.967 _reflns_number_total 2909 _reflns_number_gt 2406 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0627P)^2^+0.0356P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 2909 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 0.97 _refine_ls_restrained_S_all 0.97 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(11) _refine_diff_density_max 0.19 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 S S 0.49878(6) 0.48424(4) 0.50138(4) 0.02991(18) Uani 1 1 d . . . O O 0.39801(18) 0.40471(18) 0.54349(12) 0.0462(5) Uani 1 1 d . . . C1 C 0.4244(4) 0.7799(3) 0.4158(3) 0.0573(9) Uani 1 1 d . . . H1B H 0.437(4) 0.776(3) 0.481(3) 0.082(12) Uiso 1 1 d . . . H1A H 0.438(3) 0.853(3) 0.388(2) 0.075(11) Uiso 1 1 d . . . C2 C 0.5439(3) 0.7042(2) 0.3779(2) 0.0442(7) Uani 1 1 d . . . H2B H 0.604(3) 0.688(2) 0.423(2) 0.047(8) Uiso 1 1 d . . . H2A H 0.591(3) 0.745(2) 0.3323(19) 0.046(8) Uiso 1 1 d . . . C3 C 0.4974(3) 0.59334(18) 0.33408(15) 0.0320(5) Uani 1 1 d . . . C4 C 0.4569(2) 0.49593(19) 0.38326(16) 0.0281(5) Uani 1 1 d . . . C5 C 0.3631(3) 0.4193(2) 0.34784(17) 0.0316(6) Uani 1 1 d . . . H5 H 0.326(2) 0.366(2) 0.3901(17) 0.031(7) Uiso 1 1 d . . . C6 C 0.3089(3) 0.4365(2) 0.26195(17) 0.0347(6) Uani 1 1 d . . . C7 C 0.3727(3) 0.5165(2) 0.20623(18) 0.0402(7) Uani 1 1 d . . . H7 H 0.339(3) 0.529(2) 0.146(2) 0.050(8) Uiso 1 1 d . . . C8 C 0.4663(3) 0.5918(3) 0.24214(18) 0.0405(7) Uani 1 1 d . . . H8 H 0.499(3) 0.650(3) 0.2090(19) 0.053(8) Uiso 1 1 d . . . C9 C 0.1712(3) 0.3912(3) 0.2367(2) 0.0475(8) Uani 1 1 d . . . H9B H 0.162(3) 0.319(3) 0.254(2) 0.072(11) Uiso 1 1 d . . . H9A H 0.158(4) 0.390(3) 0.169(3) 0.081(11) Uiso 1 1 d . . . C10 C 0.0552(4) 0.4639(5) 0.2757(4) 0.0710(12) Uani 1 1 d . . . H10B H 0.009(5) 0.421(4) 0.312(3) 0.109(17) Uiso 1 1 d . . . H10A H -0.006(5) 0.481(4) 0.232(3) 0.119(18) Uiso 1 1 d . . . C11 C 0.1000(3) 0.5747(3) 0.3230(2) 0.0486(8) Uani 1 1 d . . . C12 C 0.1340(3) 0.5734(3) 0.41418(19) 0.0461(7) Uani 1 1 d . . . H12 H 0.103(3) 0.502(3) 0.4540(19) 0.055(8) Uiso 1 1 d . . . C13 C 0.2265(3) 0.6526(3) 0.4484(2) 0.0422(7) Uani 1 1 d . . . H13 H 0.262(3) 0.641(3) 0.512(2) 0.054(8) Uiso 1 1 d . . . C14 C 0.2875(3) 0.7322(2) 0.39264(19) 0.0423(7) Uani 1 1 d . . . C15 C 0.2299(3) 0.7489(3) 0.3073(2) 0.0515(8) Uani 1 1 d . . . H15 H 0.267(3) 0.806(3) 0.268(2) 0.064(9) Uiso 1 1 d . . . C16 C 0.1376(3) 0.6697(3) 0.2727(2) 0.0533(8) Uani 1 1 d . . . H16 H 0.107(3) 0.675(2) 0.206(2) 0.056(8) Uiso 1 1 d . . . C17 C 0.6584(2) 0.4009(2) 0.4962(2) 0.0372(6) Uani 1 1 d . . . C18 C 0.7612(3) 0.4682(4) 0.4407(3) 0.0597(10) Uani 1 1 d . . . H18C H 0.782(4) 0.554(4) 0.466(3) 0.100(14) Uiso 1 1 d . . . H18B H 0.728(3) 0.474(3) 0.372(2) 0.065(9) Uiso 1 1 d . . . H18A H 0.841(4) 0.424(3) 0.449(2) 0.083(12) Uiso 1 1 d . . . C19 C 0.7038(4) 0.3929(3) 0.5949(2) 0.0507(8) Uani 1 1 d . . . H19C H 0.726(4) 0.472(4) 0.618(3) 0.094(13) Uiso 1 1 d . . . H19A H 0.637(4) 0.352(3) 0.629(2) 0.070(10) Uiso 1 1 d . . . H19B H 0.787(3) 0.355(3) 0.593(2) 0.066(10) Uiso 1 1 d . . . C20 C 0.6299(5) 0.2820(3) 0.4571(3) 0.0606(10) Uani 1 1 d . . . H20C H 0.721(4) 0.237(4) 0.457(3) 0.105(14) Uiso 1 1 d . . . H20A H 0.564(4) 0.250(3) 0.490(3) 0.072(13) Uiso 1 1 d . . . H20B H 0.603(3) 0.284(3) 0.396(2) 0.057(9) Uiso 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 S 0.0279(3) 0.0329(3) 0.0289(3) 0.0010(3) 0.0003(3) 0.0004(3) O 0.0368(10) 0.0628(13) 0.0391(10) 0.0199(9) 0.0019(8) -0.0089(10) C1 0.062(2) 0.0405(19) 0.069(2) -0.0127(17) -0.0034(17) -0.0066(16) C2 0.0438(17) 0.0353(15) 0.0535(18) 0.0086(14) -0.0072(16) -0.0092(12) C3 0.0270(12) 0.0322(12) 0.0370(14) 0.0049(10) 0.0015(11) -0.0010(13) C4 0.0247(11) 0.0284(12) 0.0311(14) -0.0017(10) 0.0026(10) 0.0050(10) C5 0.0335(14) 0.0254(13) 0.0359(14) 0.0002(11) 0.0028(11) 0.0022(12) C6 0.0384(14) 0.0313(13) 0.0344(15) -0.0090(11) -0.0074(11) 0.0068(12) C7 0.0466(17) 0.0475(17) 0.0265(15) 0.0005(12) 0.0011(12) 0.0114(15) C8 0.0406(17) 0.0432(15) 0.0378(16) 0.0105(13) 0.0081(13) 0.0019(13) C9 0.0449(18) 0.0417(18) 0.056(2) -0.0039(15) -0.0180(15) -0.0017(14) C10 0.045(2) 0.091(3) 0.077(3) -0.037(2) 0.003(2) -0.013(2) C11 0.0309(15) 0.067(2) 0.0482(19) -0.0207(16) 0.0006(13) 0.0081(15) C12 0.0318(16) 0.0598(19) 0.0467(18) -0.0093(15) 0.0087(13) 0.0066(14) C13 0.0387(16) 0.0491(18) 0.0389(16) -0.0107(14) -0.0007(14) 0.0152(14) C14 0.0484(17) 0.0331(14) 0.0455(17) -0.0104(12) -0.0022(14) 0.0111(13) C15 0.060(2) 0.0437(17) 0.0510(19) 0.0022(15) 0.0008(16) 0.0154(17) C16 0.0489(18) 0.069(2) 0.0417(17) -0.0134(16) -0.0114(15) 0.0237(17) C17 0.0297(13) 0.0381(14) 0.0438(14) -0.0023(14) -0.0075(13) 0.0059(10) C18 0.0257(16) 0.090(3) 0.063(2) 0.0031(19) 0.0015(15) 0.0075(18) C19 0.0460(19) 0.060(2) 0.0464(18) 0.0021(16) -0.0139(16) 0.0100(17) C20 0.064(3) 0.049(2) 0.069(2) -0.0163(18) -0.023(2) 0.0205(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S O 1.4943(18) . ? S C4 1.796(2) . ? S C17 1.857(2) . ? C1 C14 1.507(4) . ? C1 C2 1.577(5) . ? C2 C3 1.509(4) . ? C3 C8 1.391(4) . ? C3 C4 1.399(3) . ? C4 C5 1.388(3) . ? C5 C6 1.391(4) . ? C6 C7 1.391(4) . ? C6 C9 1.511(4) . ? C7 C8 1.380(4) . ? C9 C10 1.537(5) . ? C10 C11 1.526(5) . ? C11 C16 1.377(5) . ? C11 C12 1.387(4) . ? C12 C13 1.392(4) . ? C13 C14 1.375(4) . ? C14 C15 1.396(4) . ? C15 C16 1.392(5) . ? C17 C20 1.518(4) . ? C17 C18 1.523(4) . ? C17 C19 1.527(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 O S C4 107.11(11) . . ? O S C17 105.62(11) . . ? C4 S C17 101.36(11) . . ? C14 C1 C2 113.3(2) . . ? C3 C2 C1 113.2(2) . . ? C8 C3 C4 115.5(2) . . ? C8 C3 C2 119.8(2) . . ? C4 C3 C2 123.4(2) . . ? C5 C4 C3 120.8(2) . . ? C5 C4 S 118.21(18) . . ? C3 C4 S 119.79(17) . . ? C6 C5 C4 120.8(2) . . ? C5 C6 C7 117.2(2) . . ? C5 C6 C9 121.7(3) . . ? C7 C6 C9 119.8(3) . . ? C8 C7 C6 120.0(2) . . ? C7 C8 C3 122.2(2) . . ? C6 C9 C10 113.4(3) . . ? C11 C10 C9 114.3(3) . . ? C16 C11 C12 117.7(3) . . ? C16 C11 C10 120.2(3) . . ? C12 C11 C10 120.4(4) . . ? C11 C12 C13 120.4(3) . . ? C14 C13 C12 121.0(3) . . ? C13 C14 C15 116.8(3) . . ? C13 C14 C1 120.5(3) . . ? C15 C14 C1 121.6(3) . . ? C16 C15 C14 120.6(3) . . ? C11 C16 C15 120.4(3) . . ? C20 C17 C18 112.5(3) . . ? C20 C17 C19 111.3(3) . . ? C18 C17 C19 110.2(3) . . ? C20 C17 S 109.1(2) . . ? C18 C17 S 109.2(2) . . ? C19 C17 S 104.1(2) . . ? #===END data_jul2004 _database_code_depnum_ccdc_archive 'CCDC 278338' _audit_creation_date 2004-07-21T14:25:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H24 O1 S1' _chemical_formula_sum 'C20 H24 O1 S1' _chemical_formula_weight 312.45 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.9622(3) _cell_length_b 11.5421(3) _cell_length_c 14.9696(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1721.28(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 15410 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.197426E-1 _diffrn_orient_matrix_ub_12 -0.492042E-1 _diffrn_orient_matrix_ub_13 -0.533909E-1 _diffrn_orient_matrix_ub_21 0.391286E-1 _diffrn_orient_matrix_ub_22 0.687277E-1 _diffrn_orient_matrix_ub_23 -0.312465E-1 _diffrn_orient_matrix_ub_31 0.903062E-1 _diffrn_orient_matrix_ub_32 -0.190219E-1 _diffrn_orient_matrix_ub_33 0.252109E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_unetI/netI 0.0349 _diffrn_reflns_number 23660 _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 -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 3022 _reflns_number_gt 2694 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0606P)^2^+0.2763P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 3022 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(9) _refine_diff_density_max 0.341 _refine_diff_density_min -0.16 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 S S 0.96363(6) 0.53669(5) 0.24181(4) 0.03489(18) Uani 1 1 d . . . O O 0.9185(2) 0.64307(18) 0.29029(12) 0.0539(6) Uani 1 1 d . . . C1 C 0.6594(3) 0.7313(4) 0.1713(3) 0.0676(10) Uani 1 1 d . . . H1B H 0.664(5) 0.729(4) 0.229(3) 0.108(17) Uiso 1 1 d . . . H1A H 0.610(4) 0.794(3) 0.147(2) 0.068(10) Uiso 1 1 d . . . C2 C 0.8010(3) 0.7430(3) 0.1243(2) 0.0506(7) Uani 1 1 d . . . H2A H 0.791(3) 0.799(3) 0.080(2) 0.058(9) Uiso 1 1 d . . . H2B H 0.867(3) 0.775(3) 0.172(2) 0.066(9) Uiso 1 1 d . . . C3 C 0.8474(2) 0.6291(2) 0.08301(17) 0.0351(6) Uani 1 1 d . . . C4 C 0.8933(2) 0.5332(2) 0.13145(14) 0.0304(5) Uani 1 1 d . . . C5 C 0.8744(3) 0.4219(2) 0.09843(17) 0.0350(6) Uani 1 1 d . . . H5 H 0.899(3) 0.361(2) 0.1388(18) 0.043(7) Uiso 1 1 d . . . C6 C 0.8165(3) 0.4027(2) 0.01510(17) 0.0388(6) Uani 1 1 d . . . C7 C 0.8035(3) 0.4982(2) -0.03996(17) 0.0419(6) Uani 1 1 d . . . H7 H 0.766(3) 0.487(3) -0.098(2) 0.056(8) Uiso 1 1 d . . . C8 C 0.8194(3) 0.6088(2) -0.00632(17) 0.0408(6) Uani 1 1 d . . . H8 H 0.791(3) 0.677(3) -0.041(2) 0.054(8) Uiso 1 1 d . . . C9 C 0.7459(3) 0.2906(3) -0.0067(2) 0.0514(8) Uani 1 1 d . . . H9A H 0.786(3) 0.223(3) 0.0212(19) 0.051(8) Uiso 1 1 d . . . H9B H 0.736(4) 0.275(3) -0.077(3) 0.096(12) Uiso 1 1 d . . . C10 C 0.5951(3) 0.2919(3) 0.0195(3) 0.0636(9) Uani 1 1 d . . . H10A H 0.578(3) 0.247(3) 0.069(2) 0.057(10) Uiso 1 1 d . . . H10B H 0.540(4) 0.291(3) -0.048(3) 0.088(11) Uiso 1 1 d . . . C11 C 0.5542(3) 0.4003(3) 0.0715(2) 0.0480(7) Uani 1 1 d . . . C12 C 0.5795(3) 0.4122(3) 0.1611(2) 0.0532(8) Uani 1 1 d . . . H12 H 0.599(3) 0.328(3) 0.2157(19) 0.064 Uiso 1 1 d . . . C13 C 0.5941(3) 0.5231(4) 0.1983(2) 0.0560(9) Uani 1 1 d . . . H13 H 0.617(3) 0.535(3) 0.254(2) 0.067(9) Uiso 1 1 d . . . C14 C 0.5849(3) 0.6222(3) 0.1453(2) 0.0488(7) Uani 1 1 d . . . C15 C 0.5299(3) 0.6080(3) 0.06102(19) 0.0461(7) Uani 1 1 d . . . H15 H 0.509(2) 0.681(2) 0.0264(16) 0.037(7) Uiso 1 1 d . . . C16 C 0.5145(2) 0.4977(3) 0.02524(19) 0.0480(7) Uani 1 1 d . . . H16 H 0.474(3) 0.491(2) -0.0401(18) 0.053(7) Uiso 1 1 d . . . C17 C 1.1434(2) 0.5602(2) 0.21283(16) 0.0354(6) Uani 1 1 d . . . C18 C 1.1615(3) 0.6750(3) 0.1655(2) 0.0510(8) Uani 1 1 d . . . H18A H 1.117(3) 0.673(3) 0.106(2) 0.058(9) Uiso 1 1 d . . . H18B H 1.117(3) 0.732(3) 0.197(2) 0.061(10) Uiso 1 1 d . . . H18C H 1.265(4) 0.689(3) 0.157(2) 0.065(9) Uiso 1 1 d . . . C19 C 1.2143(3) 0.5618(3) 0.30294(19) 0.0449(7) Uani 1 1 d . . . H19A H 1.165(4) 0.628(3) 0.342(2) 0.071(10) Uiso 1 1 d . . . H19B H 1.316(4) 0.566(3) 0.294(2) 0.080(11) Uiso 1 1 d . . . H19C H 1.197(3) 0.492(3) 0.3363(19) 0.050(8) Uiso 1 1 d . . . C20 C 1.1897(3) 0.4582(3) 0.15641(19) 0.0477(7) Uani 1 1 d . . . H20A H 1.294(4) 0.456(3) 0.156(2) 0.091(11) Uiso 1 1 d . . . H20B H 1.154(3) 0.378(3) 0.190(2) 0.068(10) Uiso 1 1 d . . . H20C H 1.153(3) 0.461(2) 0.0967(17) 0.039(7) Uiso 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 S 0.0334(3) 0.0415(3) 0.0297(3) -0.0022(3) 0.0041(2) -0.0056(3) O 0.0485(12) 0.0680(14) 0.0452(10) -0.0257(10) 0.0050(9) 0.0085(10) C1 0.0458(19) 0.065(2) 0.092(3) -0.030(2) 0.0012(19) 0.0146(17) C2 0.0478(17) 0.0366(16) 0.067(2) -0.0071(15) -0.0072(15) 0.0089(14) C3 0.0311(13) 0.0304(13) 0.0437(14) 0.0028(11) 0.0050(11) -0.0005(11) C4 0.0268(11) 0.0333(12) 0.0310(11) -0.0021(11) 0.0035(9) -0.0008(11) C5 0.0322(14) 0.0319(14) 0.0411(14) 0.0003(11) -0.0008(11) 0.0037(11) C6 0.0352(13) 0.0405(14) 0.0406(14) -0.0108(11) -0.0006(11) 0.0063(12) C7 0.0359(13) 0.0589(18) 0.0308(13) -0.0028(12) 0.0002(11) 0.0044(12) C8 0.0335(14) 0.0469(16) 0.0418(15) 0.0123(12) 0.0027(12) 0.0032(12) C9 0.0561(18) 0.0402(16) 0.0578(19) -0.0140(14) -0.0167(15) 0.0048(14) C10 0.0482(18) 0.056(2) 0.086(3) -0.011(2) -0.0062(18) -0.0094(16) C11 0.0285(14) 0.0547(18) 0.0607(18) -0.0021(14) -0.0020(13) -0.0107(14) C12 0.0316(15) 0.068(2) 0.0596(19) 0.0129(16) 0.0052(13) -0.0080(14) C13 0.0285(13) 0.104(3) 0.0350(15) -0.0021(18) 0.0022(11) 0.0012(17) C14 0.0298(14) 0.0625(18) 0.0541(17) -0.0188(15) 0.0045(12) 0.0090(13) C15 0.0284(13) 0.0554(18) 0.0546(17) 0.0023(13) -0.0001(13) 0.0109(14) C16 0.0287(13) 0.067(2) 0.0486(15) -0.0047(14) -0.0080(12) -0.0019(12) C17 0.0298(12) 0.0384(14) 0.0379(12) 0.0025(11) 0.0025(10) -0.0022(10) C18 0.0403(17) 0.0534(19) 0.059(2) 0.0172(16) -0.0012(16) -0.0105(15) C19 0.0423(17) 0.0477(18) 0.0448(15) 0.0012(13) -0.0078(12) -0.0053(14) C20 0.0370(14) 0.0611(19) 0.0451(16) -0.0058(16) 0.0012(12) 0.0116(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S O 1.495(2) . ? S C4 1.795(2) . ? S C17 1.863(2) . ? C1 C14 1.512(5) . ? C1 C2 1.583(5) . ? C2 C3 1.524(4) . ? C3 C8 1.386(4) . ? C3 C4 1.400(3) . ? C4 C5 1.390(4) . ? C5 C6 1.392(4) . ? C6 C7 1.383(4) . ? C6 C9 1.508(4) . ? C7 C8 1.381(4) . ? C9 C10 1.553(5) . ? C10 C11 1.529(4) . ? C11 C12 1.371(5) . ? C11 C16 1.378(4) . ? C12 C13 1.404(5) . ? C13 C14 1.395(5) . ? C14 C15 1.385(4) . ? C15 C16 1.389(4) . ? C17 C18 1.512(4) . ? C17 C20 1.521(4) . ? C17 C19 1.523(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 O S C4 110.36(11) . . ? O S C17 106.38(11) . . ? C4 S C17 99.46(11) . . ? C14 C1 C2 113.2(3) . . ? C3 C2 C1 112.1(3) . . ? C8 C3 C4 115.6(2) . . ? C8 C3 C2 118.4(3) . . ? C4 C3 C2 124.8(2) . . ? C5 C4 C3 120.2(2) . . ? C5 C4 S 113.63(18) . . ? C3 C4 S 125.92(18) . . ? C4 C5 C6 121.4(2) . . ? C7 C6 C5 116.5(2) . . ? C7 C6 C9 120.8(2) . . ? C5 C6 C9 121.5(3) . . ? C8 C7 C6 120.6(2) . . ? C7 C8 C3 122.0(2) . . ? C6 C9 C10 112.8(2) . . ? C11 C10 C9 113.2(2) . . ? C12 C11 C16 117.5(3) . . ? C12 C11 C10 122.1(3) . . ? C16 C11 C10 119.2(3) . . ? C11 C12 C13 119.9(3) . . ? C14 C13 C12 121.0(3) . . ? C15 C14 C13 116.6(3) . . ? C15 C14 C1 121.8(3) . . ? C13 C14 C1 120.3(3) . . ? C14 C15 C16 120.2(3) . . ? C11 C16 C15 121.5(3) . . ? C18 C17 C20 112.5(3) . . ? C18 C17 C19 110.4(2) . . ? C20 C17 C19 111.1(2) . . ? C18 C17 S 110.56(19) . . ? C20 C17 S 107.95(18) . . ? C19 C17 S 103.99(17) . . ? #===END data_may1705 _database_code_depnum_ccdc_archive 'CCDC 283984' _audit_creation_date 2005-05-20T10:18:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H30 O2 S' _chemical_formula_sum 'C27 H30 O2 S' _chemical_formula_weight 418.57 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8751(3) _cell_length_b 13.6785(4) _cell_length_c 16.9532(4) _cell_angle_alpha 74.165(2) _cell_angle_beta 75.054(2) _cell_angle_gamma 69.839(1) _cell_volume 2239.71(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 22721 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.408738E-1 _diffrn_orient_matrix_ub_12 0.109711E-1 _diffrn_orient_matrix_ub_13 0.421814E-1 _diffrn_orient_matrix_ub_21 -0.37384E-1 _diffrn_orient_matrix_ub_22 0.78749E-1 _diffrn_orient_matrix_ub_23 -0.176225E-1 _diffrn_orient_matrix_ub_31 -0.827865E-1 _diffrn_orient_matrix_ub_32 -0.19067E-2 _diffrn_orient_matrix_ub_33 0.423955E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_unetI/netI 0.047 _diffrn_reflns_number 34192 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 26.09 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 8788 _reflns_number_gt 6596 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0448P)^2^+0.8708P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 8788 _refine_ls_number_parameters 781 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.109 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.255 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.044 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 S S 1.02404(5) 0.18721(4) 0.88333(3) 0.02832(13) Uani 1 1 d . . . O1 O 1.01931(13) 0.11315(10) 0.96688(8) 0.0355(3) Uani 1 1 d . . . O2 O 0.74843(16) 0.06331(11) 1.02845(9) 0.0370(4) Uani 1 1 d . . . H1C H 0.828(3) 0.029(2) 1.0235(15) 0.049(8) Uiso 1 1 d . . . C1 C 1.0741(3) 0.0997(3) 0.6809(3) 0.0759(11) Uani 1 1 d . . . H1A H 1.113(4) 0.095(3) 0.632(2) 0.104(13) Uiso 1 1 d . . . H1B H 1.161(5) 0.066(4) 0.697(3) 0.153(18) Uiso 1 1 d . . . C2 C 1.0225(2) 0.21416(18) 0.69759(14) 0.0370(5) Uani 1 1 d . . . H2B H 1.093(3) 0.228(2) 0.7160(15) 0.058(7) Uiso 1 1 d . . . H2A H 1.010(2) 0.261(2) 0.6436(17) 0.064(8) Uiso 1 1 d . . . C3 C 0.88954(19) 0.23662(14) 0.75720(11) 0.0269(4) Uani 1 1 d . . . C4 C 0.87275(18) 0.21466(14) 0.84513(11) 0.0237(4) Uani 1 1 d . . . C5 C 0.75632(18) 0.19462(14) 0.89648(11) 0.0237(4) Uani 1 1 d . . . C6 C 0.65831(18) 0.19107(15) 0.85742(12) 0.0272(4) Uani 1 1 d . . . C7 C 0.6637(2) 0.23696(16) 0.77345(12) 0.0315(5) Uani 1 1 d . . . H7 H 0.592(2) 0.2428(15) 0.7495(12) 0.029(5) Uiso 1 1 d . . . C8 C 0.7757(2) 0.26115(16) 0.72446(13) 0.0313(5) Uani 1 1 d . . . H8 H 0.7788(19) 0.2837(16) 0.6670(13) 0.031(5) Uiso 1 1 d . . . C9 C 0.5631(2) 0.12547(18) 0.89803(15) 0.0371(5) Uani 1 1 d . . . H9B H 0.536(2) 0.1228(18) 0.9564(15) 0.046(7) Uiso 1 1 d . . . H9A H 0.485(3) 0.1569(19) 0.8691(15) 0.058(7) Uiso 1 1 d . . . C10 C 0.6216(3) 0.0077(2) 0.8848(2) 0.0588(7) Uani 1 1 d . . . H10B H 0.636(3) -0.040(2) 0.9391(19) 0.076(9) Uiso 1 1 d . . . H10A H 0.560(3) -0.009(3) 0.8646(19) 0.091(11) Uiso 1 1 d . . . C11 C 0.7549(2) -0.01415(16) 0.82704(14) 0.0383(5) Uani 1 1 d . . . C12 C 0.8711(3) -0.04102(16) 0.85822(15) 0.0414(6) Uani 1 1 d . . . H12 H 0.868(2) -0.0640(18) 0.9137(15) 0.047(7) Uiso 1 1 d . . . C13 C 0.9829(2) -0.01702(17) 0.80762(16) 0.0429(6) Uani 1 1 d . . . H13 H 1.054(3) -0.0241(19) 0.8308(15) 0.056(7) Uiso 1 1 d . . . C14 C 0.9820(2) 0.03283(17) 0.72506(14) 0.0395(5) Uani 1 1 d . . . C15 C 0.8781(2) 0.03495(18) 0.69102(15) 0.0411(5) Uani 1 1 d . . . H15 H 0.880(2) 0.0652(18) 0.6333(15) 0.049(7) Uiso 1 1 d . . . C16 C 0.7658(2) 0.01212(18) 0.74126(15) 0.0408(5) Uani 1 1 d . . . H16 H 0.689(2) 0.0262(18) 0.7177(14) 0.047(6) Uiso 1 1 d . . . C17 C 1.0173(2) 0.31751(16) 0.90136(13) 0.0351(5) Uani 1 1 d . . . C18 C 0.9943(3) 0.4008(2) 0.82220(18) 0.0532(7) Uani 1 1 d . . . H18B H 1.065(3) 0.378(2) 0.7739(17) 0.065(8) Uiso 1 1 d . . . H18C H 1.004(3) 0.469(2) 0.8277(16) 0.068(8) Uiso 1 1 d . . . H18A H 0.902(3) 0.411(2) 0.8103(16) 0.069(8) Uiso 1 1 d . . . C19 C 1.1562(3) 0.2967(3) 0.9193(2) 0.0618(8) Uani 1 1 d . . . H19B H 1.171(2) 0.239(2) 0.9720(17) 0.061(8) Uiso 1 1 d . . . H19C H 1.161(3) 0.364(2) 0.9299(17) 0.075(9) Uiso 1 1 d . . . H19A H 1.230(3) 0.275(3) 0.870(2) 0.091(11) Uiso 1 1 d . . . C20 C 0.9106(3) 0.3488(2) 0.97503(19) 0.0557(7) Uani 1 1 d . . . H20B H 0.924(3) 0.292(2) 1.0237(18) 0.069(9) Uiso 1 1 d . . . H20A H 0.820(3) 0.363(2) 0.9662(16) 0.063(8) Uiso 1 1 d . . . H20C H 0.920(3) 0.409(2) 0.9868(17) 0.074(8) Uiso 1 1 d . . . C21 C 0.7340(2) 0.17285(15) 0.99191(12) 0.0277(4) Uani 1 1 d . . . H21 H 0.7982(18) 0.1943(14) 1.0089(11) 0.022(5) Uiso 1 1 d . . . C22 C 0.59690(19) 0.23742(15) 1.02903(11) 0.0264(4) Uani 1 1 d . . . C23 C 0.5388(2) 0.34194(16) 0.99126(13) 0.0343(5) Uani 1 1 d . . . H23 H 0.588(2) 0.3715(16) 0.9400(13) 0.034(5) Uiso 1 1 d . . . C24 C 0.4131(2) 0.39921(19) 1.02540(14) 0.0425(5) Uani 1 1 d . . . H24 H 0.374(2) 0.471(2) 0.9973(14) 0.048(6) Uiso 1 1 d . . . C25 C 0.3430(3) 0.3528(2) 1.09739(14) 0.0445(6) Uani 1 1 d . . . H25 H 0.255(3) 0.392(2) 1.1197(15) 0.058(7) Uiso 1 1 d . . . C26 C 0.3999(2) 0.25010(19) 1.13620(14) 0.0417(5) Uani 1 1 d . . . H26 H 0.352(2) 0.2163(17) 1.1849(14) 0.042(6) Uiso 1 1 d . . . C27 C 0.5259(2) 0.19358(17) 1.10256(12) 0.0321(5) Uani 1 1 d . . . H27 H 0.5646(19) 0.1221(17) 1.1295(12) 0.030(5) Uiso 1 1 d . . . S1B S 0.37927(5) 0.45489(4) 0.38235(3) 0.02502(12) Uani 1 1 d . A 1 O1B O 0.36655(14) 0.49292(10) 0.46051(8) 0.0326(3) Uani 1 1 d . A 1 O2B O 0.62559(16) 0.30146(13) 0.56258(9) 0.0408(4) Uani 1 1 d . A 1 H2D H 0.614(2) 0.366(2) 0.5522(14) 0.043(7) Uiso 1 1 d . B 1 C1B C 0.6414(4) 0.5007(4) 0.1984(3) 0.0880(13) Uani 1 1 d . A 1 H1Y H 0.593(7) 0.572(6) 0.202(4) 0.26(4) Uiso 1 1 d . C 1 H1X H 0.675(3) 0.513(3) 0.142(2) 0.102(12) Uiso 1 1 d . D 1 C2B C 0.5502(2) 0.4284(2) 0.21174(13) 0.0381(5) Uani 1 1 d . A 1 H2X H 0.571(3) 0.399(2) 0.1618(17) 0.065(8) Uiso 1 1 d . E 1 H2Y H 0.460(3) 0.4750(19) 0.2145(14) 0.048(7) Uiso 1 1 d . F 1 C3B C 0.57285(19) 0.33574(16) 0.28549(11) 0.0282(4) Uani 1 1 d . A 1 C4B C 0.52242(17) 0.34093(14) 0.37053(11) 0.0228(4) Uani 1 1 d . A 1 C5B C 0.58981(19) 0.27122(14) 0.43468(12) 0.0263(4) Uani 1 1 d . A 1 C6B C 0.7126(2) 0.19682(15) 0.41064(13) 0.0323(5) Uani 1 1 d . A 1 C7B C 0.7403(2) 0.17610(17) 0.33138(14) 0.0365(5) Uani 1 1 d . A 1 H7X H 0.819(2) 0.1193(18) 0.3167(13) 0.042(6) Uiso 1 1 d . G 1 C8B C 0.6712(2) 0.24282(17) 0.27028(13) 0.0341(5) Uani 1 1 d . A 1 H8X H 0.704(2) 0.2333(18) 0.2143(14) 0.045(6) Uiso 1 1 d . H 1 C9B C 0.8234(3) 0.1484(2) 0.46118(18) 0.0484(6) Uani 1 1 d . A 1 H9Y H 0.790(2) 0.1475(18) 0.5194(15) 0.046(7) Uiso 1 1 d . I 1 H9X H 0.867(3) 0.071(2) 0.4564(15) 0.066(8) Uiso 1 1 d . J 1 C10B C 0.9345(3) 0.2062(3) 0.4315(2) 0.0709(9) Uani 1 1 d . A 1 H10Y H 0.947(3) 0.224(2) 0.477(2) 0.081(10) Uiso 1 1 d . K 1 H10X H 1.010(4) 0.160(3) 0.420(2) 0.104(13) Uiso 1 1 d . L 1 C11B C 0.9034(2) 0.3036(2) 0.36326(15) 0.0463(6) Uani 1 1 d . A 1 C12B C 0.8104(2) 0.3966(2) 0.38230(17) 0.0473(6) Uani 1 1 d . A 1 H12X H 0.788(2) 0.4021(19) 0.4378(15) 0.049(7) Uiso 1 1 d . M 1 C13B C 0.7368(3) 0.4679(2) 0.32510(18) 0.0497(6) Uani 1 1 d . A 1 H13X H 0.663(3) 0.525(2) 0.3435(16) 0.066(8) Uiso 1 1 d . N 1 C14B C 0.7548(3) 0.4501(2) 0.24575(16) 0.0529(7) Uani 1 1 d . A 1 C15B C 0.8683(3) 0.3705(3) 0.22168(18) 0.0583(8) Uani 1 1 d . A 1 H15X H 0.889(3) 0.359(2) 0.1661(18) 0.068(8) Uiso 1 1 d . O 1 C16B C 0.9421(3) 0.2975(2) 0.27961(18) 0.0534(7) Uani 1 1 d . A 1 H16X H 1.007(3) 0.238(2) 0.2643(16) 0.061(8) Uiso 1 1 d . P 1 C17B C 0.23795(18) 0.39904(15) 0.40044(12) 0.0280(4) Uani 1 1 d . A 1 C18B C 0.2560(2) 0.3471(2) 0.32762(16) 0.0421(6) Uani 1 1 d . A 1 H18X H 0.333(3) 0.282(2) 0.3286(14) 0.050(7) Uiso 1 1 d . Q 1 H18Y H 0.269(3) 0.397(2) 0.2731(17) 0.065(8) Uiso 1 1 d . R 1 H18Z H 0.174(3) 0.3274(19) 0.3306(14) 0.055(7) Uiso 1 1 d . S 1 C19B C 0.1169(2) 0.4977(2) 0.39896(16) 0.0404(5) Uani 1 1 d . A 1 H19Z H 0.107(2) 0.536(2) 0.4414(15) 0.053(7) Uiso 1 1 d . T 1 H19Y H 0.032(3) 0.4757(19) 0.4084(14) 0.055(7) Uiso 1 1 d . U 1 H19X H 0.126(2) 0.548(2) 0.3439(16) 0.059(7) Uiso 1 1 d . V 1 C20B C 0.2281(2) 0.3218(2) 0.48334(15) 0.0416(6) Uani 1 1 d . A 1 H20Z H 0.304(2) 0.2578(19) 0.4840(13) 0.040(6) Uiso 1 1 d . W 1 H20X H 0.149(2) 0.3007(18) 0.4927(13) 0.047(6) Uiso 1 1 d . X 1 H20Y H 0.224(2) 0.356(2) 0.5307(16) 0.060(8) Uiso 1 1 d . Y 1 C21B C 0.5354(2) 0.27899(16) 0.52608(12) 0.0290(4) Uani 1 1 d . A 1 H21X H 0.449(2) 0.3362(16) 0.5295(11) 0.026(5) Uiso 1 1 d . Z 1 C22B C 0.5033(2) 0.17963(15) 0.58290(12) 0.0302(4) Uani 1 1 d . A 1 C23B C 0.5420(2) 0.08070(17) 0.56185(14) 0.0400(5) Uani 1 1 d . A 1 H23X H 0.592(2) 0.0733(17) 0.5070(14) 0.042(6) Uiso 1 1 d . A 1 C24B C 0.5063(3) -0.00466(19) 0.61792(15) 0.0474(6) Uani 1 1 d . A 1 H24X H 0.539(3) -0.077(2) 0.6010(15) 0.064(7) Uiso 1 1 d . B 1 C25B C 0.4316(2) 0.00743(19) 0.69517(15) 0.0459(6) Uani 1 1 d . A 1 H25X H 0.404(2) -0.0493(18) 0.7327(13) 0.040(6) Uiso 1 1 d . C 1 C26B C 0.3914(2) 0.1055(2) 0.71748(15) 0.0422(6) Uani 1 1 d . A 1 H26X H 0.341(2) 0.1139(18) 0.7697(15) 0.044(6) Uiso 1 1 d . D 1 C27B C 0.4265(2) 0.19089(18) 0.66175(13) 0.0353(5) Uani 1 1 d . A 1 H27X H 0.396(2) 0.2610(19) 0.6772(14) 0.050(7) Uiso 1 1 d . E 1 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 S 0.0220(3) 0.0260(3) 0.0365(3) -0.0047(2) -0.0077(2) -0.0060(2) O1 0.0331(8) 0.0303(8) 0.0417(8) 0.0018(6) -0.0176(6) -0.0070(6) O2 0.0334(9) 0.0263(8) 0.0394(9) 0.0026(6) -0.0041(7) -0.0031(7) C1 0.0491(19) 0.061(2) 0.115(3) -0.050(2) 0.0341(19) -0.0239(16) C2 0.0350(13) 0.0399(13) 0.0318(12) -0.0074(10) 0.0004(9) -0.0101(10) C3 0.0298(11) 0.0220(10) 0.0269(10) -0.0048(8) -0.0022(8) -0.0074(8) C4 0.0217(10) 0.0185(9) 0.0306(10) -0.0054(8) -0.0070(8) -0.0036(7) C5 0.0229(10) 0.0185(9) 0.0276(10) -0.0050(7) -0.0064(8) -0.0018(7) C6 0.0233(10) 0.0265(10) 0.0325(11) -0.0105(8) -0.0058(8) -0.0040(8) C7 0.0292(11) 0.0336(11) 0.0342(11) -0.0106(9) -0.0122(9) -0.0049(9) C8 0.0382(12) 0.0281(11) 0.0260(11) -0.0050(8) -0.0092(9) -0.0056(9) C9 0.0298(12) 0.0481(14) 0.0415(13) -0.0142(10) -0.0054(10) -0.0182(10) C10 0.0632(19) 0.0511(16) 0.0683(19) -0.0226(15) 0.0134(15) -0.0350(14) C11 0.0483(14) 0.0271(11) 0.0460(13) -0.0116(9) -0.0074(10) -0.0167(10) C12 0.0655(17) 0.0247(11) 0.0336(13) -0.0087(9) -0.0200(12) -0.0027(11) C13 0.0383(13) 0.0327(12) 0.0645(17) -0.0267(11) -0.0254(12) 0.0059(10) C14 0.0301(12) 0.0323(12) 0.0540(14) -0.0242(10) -0.0009(10) 0.0005(9) C15 0.0485(14) 0.0361(12) 0.0345(13) -0.0127(10) -0.0102(11) -0.0010(10) C16 0.0387(13) 0.0408(13) 0.0512(14) -0.0198(11) -0.0180(11) -0.0067(10) C17 0.0350(12) 0.0301(11) 0.0469(13) -0.0075(9) -0.0113(10) -0.0152(9) C18 0.070(2) 0.0354(14) 0.0626(18) 0.0005(12) -0.0189(15) -0.0287(14) C19 0.0507(18) 0.0561(18) 0.094(2) -0.0136(18) -0.0304(17) -0.0233(14) C20 0.064(2) 0.0470(16) 0.0671(19) -0.0271(15) -0.0028(15) -0.0251(14) C21 0.0279(11) 0.0262(10) 0.0285(10) -0.0019(8) -0.0072(8) -0.0089(8) C22 0.0297(11) 0.0289(10) 0.0250(10) -0.0083(8) -0.0065(8) -0.0107(8) C23 0.0391(12) 0.0308(11) 0.0286(11) -0.0061(9) -0.0029(9) -0.0069(10) C24 0.0458(14) 0.0357(13) 0.0400(13) -0.0138(10) -0.0093(11) 0.0014(11) C25 0.0382(14) 0.0503(15) 0.0445(14) -0.0259(12) 0.0010(11) -0.0059(12) C26 0.0461(14) 0.0511(15) 0.0314(12) -0.0170(11) 0.0081(10) -0.0232(12) C27 0.0388(12) 0.0328(12) 0.0284(11) -0.0080(9) -0.0044(9) -0.0148(10) S1B 0.0264(3) 0.0222(2) 0.0270(3) -0.00442(19) -0.00530(19) -0.00790(19) O1B 0.0411(8) 0.0255(7) 0.0350(8) -0.0133(6) -0.0088(6) -0.0075(6) O2B 0.0668(11) 0.0304(9) 0.0394(9) -0.0012(7) -0.0282(8) -0.0228(8) C1B 0.096(3) 0.095(3) 0.087(3) 0.044(2) -0.048(2) -0.071(2) C2B 0.0384(14) 0.0499(14) 0.0251(11) -0.0034(10) -0.0032(9) -0.0169(11) C3B 0.0258(10) 0.0366(11) 0.0290(10) -0.0093(8) -0.0041(8) -0.0161(9) C4B 0.0222(10) 0.0228(9) 0.0271(10) -0.0079(7) -0.0030(7) -0.0100(8) C5B 0.0298(11) 0.0216(9) 0.0329(10) -0.0073(8) -0.0087(8) -0.0108(8) C6B 0.0315(11) 0.0250(10) 0.0430(12) -0.0103(9) -0.0108(9) -0.0058(9) C7B 0.0281(12) 0.0332(12) 0.0511(14) -0.0218(10) -0.0001(10) -0.0076(10) C8B 0.0337(12) 0.0430(13) 0.0326(12) -0.0185(10) 0.0025(9) -0.0180(10) C9B 0.0425(14) 0.0384(14) 0.0632(18) -0.0147(12) -0.0248(13) 0.0038(11) C10B 0.0455(18) 0.085(2) 0.090(2) -0.0157(19) -0.0348(17) -0.0147(17) C11B 0.0274(12) 0.0633(16) 0.0610(16) -0.0278(13) -0.0089(11) -0.0168(11) C12B 0.0414(14) 0.0656(17) 0.0525(16) -0.0327(13) 0.0058(12) -0.0317(13) C13B 0.0380(14) 0.0429(15) 0.0748(19) -0.0181(13) 0.0019(13) -0.0241(12) C14B 0.0528(16) 0.0569(16) 0.0581(16) 0.0039(13) -0.0095(13) -0.0397(14) C15B 0.066(2) 0.089(2) 0.0455(16) -0.0249(15) 0.0072(14) -0.0589(18) C16B 0.0328(14) 0.0707(19) 0.0714(19) -0.0435(16) 0.0099(13) -0.0251(14) C17B 0.0224(10) 0.0317(11) 0.0310(10) -0.0063(8) -0.0043(8) -0.0099(8) C18B 0.0307(13) 0.0560(16) 0.0508(15) -0.0256(13) -0.0067(11) -0.0159(12) C19B 0.0280(12) 0.0434(14) 0.0443(14) -0.0093(12) -0.0061(10) -0.0037(10) C20B 0.0330(13) 0.0436(14) 0.0476(14) 0.0041(11) -0.0089(11) -0.0195(12) C21B 0.0376(12) 0.0246(10) 0.0282(10) -0.0069(8) -0.0124(9) -0.0077(9) C22B 0.0364(11) 0.0303(11) 0.0295(11) -0.0035(8) -0.0165(9) -0.0109(9) C23B 0.0602(15) 0.0307(12) 0.0340(12) -0.0054(10) -0.0157(11) -0.0151(11) C24B 0.0746(18) 0.0346(13) 0.0431(14) 0.0010(11) -0.0273(13) -0.0235(13) C25B 0.0601(16) 0.0451(14) 0.0433(14) 0.0104(11) -0.0266(12) -0.0313(13) C26B 0.0418(14) 0.0575(16) 0.0334(13) -0.0010(11) -0.0112(11) -0.0255(12) C27B 0.0342(12) 0.0397(13) 0.0358(12) -0.0063(10) -0.0119(9) -0.0126(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S O1 1.5001(14) . ? S C4 1.8051(18) . ? S C17 1.863(2) . ? O2 C21 1.427(2) . ? O2 H1C 0.83(3) . ? C1 C14 1.506(4) . ? C1 C2 1.550(4) . ? C1 H1A 0.84(4) . ? C1 H1B 0.97(5) . ? C2 C3 1.521(3) . ? C2 H2B 0.99(3) . ? C2 H2A 0.97(3) . ? C3 C8 1.385(3) . ? C3 C4 1.414(3) . ? C4 C5 1.406(3) . ? C5 C6 1.412(2) . ? C5 C21 1.533(3) . ? C6 C7 1.385(3) . ? C6 C9 1.512(3) . ? C7 C8 1.374(3) . ? C7 H7 0.94(2) . ? C8 H8 0.93(2) . ? C9 C10 1.571(3) . ? C9 H9B 0.95(2) . ? C9 H9A 0.99(3) . ? C10 C11 1.510(3) . ? C10 H10B 0.99(3) . ? C10 H10A 0.94(3) . ? C11 C16 1.383(3) . ? C11 C12 1.390(3) . ? C12 C13 1.380(3) . ? C12 H12 0.90(2) . ? C13 C14 1.380(3) . ? C13 H13 0.92(3) . ? C14 C15 1.384(3) . ? C15 C16 1.377(3) . ? C15 H15 0.95(2) . ? C16 H16 0.95(2) . ? C17 C20 1.513(4) . ? C17 C18 1.518(3) . ? C17 C19 1.532(3) . ? C18 H18B 1.01(3) . ? C18 H18C 1.01(3) . ? C18 H18A 1.02(3) . ? C19 H19B 1.02(3) . ? C19 H19C 1.00(3) . ? C19 H19A 1.02(3) . ? C20 H20B 0.97(3) . ? C20 H20A 0.97(3) . ? C20 H20C 0.95(3) . ? C21 C22 1.520(3) . ? C21 H21 0.973(19) . ? C22 C27 1.387(3) . ? C22 C23 1.393(3) . ? C23 C24 1.385(3) . ? C23 H23 0.96(2) . ? C24 C25 1.380(3) . ? C24 H24 0.97(2) . ? C25 C26 1.377(3) . ? C25 H25 0.96(3) . ? C26 C27 1.381(3) . ? C26 H26 0.95(2) . ? C27 H27 0.96(2) . ? S1B O1B 1.5092(13) . ? S1B C4B 1.7973(19) . ? S1B C17B 1.8650(18) . ? O2B C21B 1.436(2) . ? O2B H2D 0.82(2) . ? C1B C14B 1.504(4) . ? C1B C2B 1.565(4) . ? C1B H1Y 0.94(7) . ? C1B H1X 0.93(4) . ? C2B C3B 1.520(3) . ? C2B H2X 0.98(3) . ? C2B H2Y 0.97(2) . ? C3B C8B 1.388(3) . ? C3B C4B 1.416(3) . ? C4B C5B 1.412(3) . ? C5B C6B 1.412(3) . ? C5B C21B 1.528(3) . ? C6B C7B 1.385(3) . ? C6B C9B 1.515(3) . ? C7B C8B 1.372(3) . ? C7B H7X 0.97(2) . ? C8B H8X 0.95(2) . ? C9B C10B 1.571(4) . ? C9B H9Y 0.96(2) . ? C9B H9X 1.02(3) . ? C10B C11B 1.510(4) . ? C10B H10Y 0.92(3) . ? C10B H10X 0.86(4) . ? C11B C12B 1.383(3) . ? C11B C16B 1.388(3) . ? C12B C13B 1.370(4) . ? C12B H12X 0.93(2) . ? C13B C14B 1.385(4) . ? C13B H13X 0.96(3) . ? C14B C15B 1.390(4) . ? C15B C16B 1.387(4) . ? C15B H15X 0.95(3) . ? C16B H16X 0.92(3) . ? C17B C20B 1.514(3) . ? C17B C18B 1.524(3) . ? C17B C19B 1.526(3) . ? C18B H18X 0.99(3) . ? C18B H18Y 1.00(3) . ? C18B H18Z 1.01(3) . ? C19B H19Z 0.96(3) . ? C19B H19Y 1.03(2) . ? C19B H19X 1.00(3) . ? C20B H20Z 0.98(2) . ? C20B H20X 0.96(2) . ? C20B H20Y 1.02(3) . ? C21B C22B 1.529(3) . ? C21B H21X 0.99(2) . ? C22B C23B 1.389(3) . ? C22B C27B 1.399(3) . ? C23B C24B 1.391(3) . ? C23B H23X 0.96(2) . ? C24B C25B 1.371(4) . ? C24B H24X 1.02(3) . ? C25B C26B 1.386(3) . ? C25B H25X 0.94(2) . ? C26B C27B 1.386(3) . ? C26B H26X 0.93(2) . ? C27B H27X 0.99(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S C4 109.72(8) . . ? O1 S C17 106.66(9) . . ? C4 S C17 104.29(9) . . ? C21 O2 H1C 109.9(17) . . ? C14 C1 C2 114.1(2) . . ? C14 C1 H1A 120(3) . . ? C2 C1 H1A 114(3) . . ? C14 C1 H1B 110(3) . . ? C2 C1 H1B 108(3) . . ? H1A C1 H1B 86(3) . . ? C3 C2 C1 113.57(19) . . ? C3 C2 H2B 113.0(14) . . ? C1 C2 H2B 108.6(15) . . ? C3 C2 H2A 108.2(15) . . ? C1 C2 H2A 105.5(16) . . ? H2B C2 H2A 107(2) . . ? C8 C3 C4 116.15(17) . . ? C8 C3 C2 117.20(18) . . ? C4 C3 C2 125.44(18) . . ? C5 C4 C3 121.85(16) . . ? C5 C4 S 123.15(13) . . ? C3 C4 S 113.74(13) . . ? C4 C5 C6 117.71(16) . . ? C4 C5 C21 123.07(16) . . ? C6 C5 C21 119.19(16) . . ? C7 C6 C5 117.54(17) . . ? C7 C6 C9 118.19(18) . . ? C5 C6 C9 123.51(17) . . ? C8 C7 C6 121.74(19) . . ? C8 C7 H7 120.5(12) . . ? C6 C7 H7 117.3(12) . . ? C7 C8 C3 120.67(18) . . ? C7 C8 H8 118.6(12) . . ? C3 C8 H8 120.0(12) . . ? C6 C9 C10 113.20(18) . . ? C6 C9 H9B 112.7(14) . . ? C10 C9 H9B 107.5(14) . . ? C6 C9 H9A 107.1(14) . . ? C10 C9 H9A 104.8(14) . . ? H9B C9 H9A 111(2) . . ? C11 C10 C9 113.79(19) . . ? C11 C10 H10B 106.1(17) . . ? C9 C10 H10B 108.5(17) . . ? C11 C10 H10A 110(2) . . ? C9 C10 H10A 109(2) . . ? H10B C10 H10A 109(3) . . ? C16 C11 C12 116.9(2) . . ? C16 C11 C10 121.9(2) . . ? C12 C11 C10 119.9(2) . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12 120.2(15) . . ? C11 C12 H12 118.6(15) . . ? C12 C13 C14 120.8(2) . . ? C12 C13 H13 119.6(15) . . ? C14 C13 H13 118.8(15) . . ? C13 C14 C15 116.9(2) . . ? C13 C14 C1 120.2(3) . . ? C15 C14 C1 121.8(3) . . ? C16 C15 C14 120.9(2) . . ? C16 C15 H15 120.7(14) . . ? C14 C15 H15 117.4(14) . . ? C15 C16 C11 120.5(2) . . ? C15 C16 H16 119.5(13) . . ? C11 C16 H16 119.1(14) . . ? C20 C17 C18 111.4(2) . . ? C20 C17 C19 110.8(2) . . ? C18 C17 C19 111.1(2) . . ? C20 C17 S 111.48(15) . . ? C18 C17 S 108.63(16) . . ? C19 C17 S 103.09(17) . . ? C17 C18 H18B 110.2(16) . . ? C17 C18 H18C 109.9(15) . . ? H18B C18 H18C 106(2) . . ? C17 C18 H18A 109.8(15) . . ? H18B C18 H18A 110(2) . . ? H18C C18 H18A 112(2) . . ? C17 C19 H19B 110.1(14) . . ? C17 C19 H19C 108.1(16) . . ? H19B C19 H19C 107(2) . . ? C17 C19 H19A 111.7(18) . . ? H19B C19 H19A 110(2) . . ? H19C C19 H19A 109(2) . . ? C17 C20 H20B 109.6(17) . . ? C17 C20 H20A 113.7(16) . . ? H20B C20 H20A 108(2) . . ? C17 C20 H20C 108.1(17) . . ? H20B C20 H20C 108(2) . . ? H20A C20 H20C 110(2) . . ? O2 C21 C22 108.01(15) . . ? O2 C21 C5 112.44(16) . . ? C22 C21 C5 112.02(15) . . ? O2 C21 H21 108.5(11) . . ? C22 C21 H21 106.4(11) . . ? C5 C21 H21 109.2(10) . . ? C27 C22 C23 117.85(19) . . ? C27 C22 C21 120.56(17) . . ? C23 C22 C21 121.59(17) . . ? C24 C23 C22 120.8(2) . . ? C24 C23 H23 121.6(12) . . ? C22 C23 H23 117.6(12) . . ? C25 C24 C23 120.2(2) . . ? C25 C24 H24 120.5(14) . . ? C23 C24 H24 119.2(14) . . ? C26 C25 C24 119.6(2) . . ? C26 C25 H25 120.5(15) . . ? C24 C25 H25 119.9(15) . . ? C25 C26 C27 120.1(2) . . ? C25 C26 H26 120.9(14) . . ? C27 C26 H26 119.1(14) . . ? C26 C27 C22 121.4(2) . . ? C26 C27 H27 119.7(12) . . ? C22 C27 H27 118.9(12) . . ? O1B S1B C4B 111.44(8) . . ? O1B S1B C17B 106.23(8) . . ? C4B S1B C17B 102.64(8) . . ? C21B O2B H2D 109.3(16) . . ? C14B C1B C2B 113.4(2) . . ? C14B C1B H1Y 116(5) . . ? C2B C1B H1Y 113(5) . . ? C14B C1B H1X 110(2) . . ? C2B C1B H1X 105(2) . . ? H1Y C1B H1X 97(4) . . ? C3B C2B C1B 112.74(19) . . ? C3B C2B H2X 107.5(15) . . ? C1B C2B H2X 108.3(15) . . ? C3B C2B H2Y 115.0(13) . . ? C1B C2B H2Y 106.4(14) . . ? H2X C2B H2Y 107(2) . . ? C8B C3B C4B 115.73(18) . . ? C8B C3B C2B 117.12(18) . . ? C4B C3B C2B 125.94(19) . . ? C5B C4B C3B 122.06(17) . . ? C5B C4B S1B 126.03(14) . . ? C3B C4B S1B 111.45(14) . . ? C4B C5B C6B 117.21(17) . . ? C4B C5B C21B 121.49(17) . . ? C6B C5B C21B 121.24(17) . . ? C7B C6B C5B 117.79(18) . . ? C7B C6B C9B 117.3(2) . . ? C5B C6B C9B 124.44(19) . . ? C8B C7B C6B 121.8(2) . . ? C8B C7B H7X 119.2(12) . . ? C6B C7B H7X 118.2(13) . . ? C7B C8B C3B 120.67(19) . . ? C7B C8B H8X 118.8(14) . . ? C3B C8B H8X 119.1(14) . . ? C6B C9B C10B 113.3(2) . . ? C6B C9B H9Y 111.9(14) . . ? C10B C9B H9Y 108.5(14) . . ? C6B C9B H9X 108.9(14) . . ? C10B C9B H9X 108.2(15) . . ? H9Y C9B H9X 106(2) . . ? C11B C10B C9B 113.3(2) . . ? C11B C10B H10Y 110(2) . . ? C9B C10B H10Y 109(2) . . ? C11B C10B H10X 114(2) . . ? C9B C10B H10X 109(3) . . ? H10Y C10B H10X 101(3) . . ? C12B C11B C16B 116.9(3) . . ? C12B C11B C10B 119.9(3) . . ? C16B C11B C10B 121.6(3) . . ? C13B C12B C11B 121.2(2) . . ? C13B C12B H12X 120.9(15) . . ? C11B C12B H12X 116.8(15) . . ? C12B C13B C14B 121.1(3) . . ? C12B C13B H13X 118.5(16) . . ? C14B C13B H13X 119.8(16) . . ? C13B C14B C15B 116.4(3) . . ? C13B C14B C1B 118.9(3) . . ? C15B C14B C1B 123.6(3) . . ? C16B C15B C14B 121.2(3) . . ? C16B C15B H15X 118.6(17) . . ? C14B C15B H15X 119.6(17) . . ? C15B C16B C11B 120.0(3) . . ? C15B C16B H16X 119.7(16) . . ? C11B C16B H16X 119.4(16) . . ? C20B C17B C18B 111.94(19) . . ? C20B C17B C19B 111.35(18) . . ? C18B C17B C19B 110.21(18) . . ? C20B C17B S1B 111.70(14) . . ? C18B C17B S1B 108.23(14) . . ? C19B C17B S1B 103.02(14) . . ? C17B C18B H18X 111.1(14) . . ? C17B C18B H18Y 111.2(15) . . ? H18X C18B H18Y 109(2) . . ? C17B C18B H18Z 110.0(14) . . ? H18X C18B H18Z 108.5(19) . . ? H18Y C18B H18Z 106.6(19) . . ? C17B C19B H19Z 112.5(15) . . ? C17B C19B H19Y 109.5(14) . . ? H19Z C19B H19Y 108.1(19) . . ? C17B C19B H19X 110.3(14) . . ? H19Z C19B H19X 107(2) . . ? H19Y C19B H19X 109.4(19) . . ? C17B C20B H20Z 111.6(12) . . ? C17B C20B H20X 108.9(13) . . ? H20Z C20B H20X 108.0(19) . . ? C17B C20B H20Y 110.8(14) . . ? H20Z C20B H20Y 108.0(19) . . ? H20X C20B H20Y 109.5(19) . . ? O2B C21B C5B 112.23(16) . . ? O2B C21B C22B 106.43(15) . . ? C5B C21B C22B 114.96(16) . . ? O2B C21B H21X 109.6(11) . . ? C5B C21B H21X 108.5(10) . . ? C22B C21B H21X 104.8(11) . . ? C23B C22B C27B 117.99(19) . . ? C23B C22B C21B 125.33(19) . . ? C27B C22B C21B 116.67(18) . . ? C22B C23B C24B 120.9(2) . . ? C22B C23B H23X 118.2(13) . . ? C24B C23B H23X 120.9(13) . . ? C25B C24B C23B 120.5(2) . . ? C25B C24B H24X 120.6(14) . . ? C23B C24B H24X 118.9(14) . . ? C24B C25B C26B 119.7(2) . . ? C24B C25B H25X 120.9(13) . . ? C26B C25B H25X 119.3(13) . . ? C27B C26B C25B 120.0(2) . . ? C27B C26B H26X 120.0(14) . . ? C25B C26B H26X 119.9(14) . . ? C26B C27B C22B 120.9(2) . . ? C26B C27B H27X 120.0(13) . . ? C22B C27B H27X 119.1(13) . . ? #===END data_jun2305 _database_code_depnum_ccdc_archive 'CCDC 283985' _audit_creation_date 2005-06-22T10:19:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H32 O2 S' _chemical_formula_sum 'C24 H32 O2 S' _chemical_formula_weight 384.56 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 42/n' _symmetry_space_group_name_Hall '-P 4bc' _symmetry_Int_Tables_number 86 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 21.1744(9) _cell_length_b 21.1744(9) _cell_length_c 9.5008(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4259.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13954 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 22.986 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.414191E-1 _diffrn_orient_matrix_ub_12 0.193651E-1 _diffrn_orient_matrix_ub_13 -0.263536E-1 _diffrn_orient_matrix_ub_21 0.174607E-1 _diffrn_orient_matrix_ub_22 0.114858E-1 _diffrn_orient_matrix_ub_23 -0.943867E-1 _diffrn_orient_matrix_ub_31 -0.144898E-1 _diffrn_orient_matrix_ub_32 -0.415144E-1 _diffrn_orient_matrix_ub_33 -0.38407E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.1631 _diffrn_reflns_av_unetI/netI 0.079 _diffrn_reflns_number 20986 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 22.96 _diffrn_reflns_theta_full 22.96 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 2935 _reflns_number_gt 1767 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Weak and limited diffraction. The H on N2 was refined; other H atoms were in riding mode. 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^)+(0.0683P)^2^+3.6511P] 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_number_reflns 2935 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1263 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.178 _refine_ls_wR_factor_gt 0.1453 _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_restrained_S_all 1.01 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.175 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 S S 0.08814(5) 0.01856(5) 0.25012(14) 0.0525(4) Uani 1 1 d . . . O1 O 0.03143(12) 0.02866(14) 0.3427(4) 0.0622(10) Uani 1 1 d . . . O2 O 0.07532(16) 0.04532(16) 0.6783(4) 0.0701(11) Uani 1 1 d . . . H2X H 0.046(2) 0.024(2) 0.637(5) 0.059(15) Uiso 1 1 d . . . C1 C 0.1552(3) -0.0900(3) 0.7615(7) 0.099(2) Uani 1 1 d . . . H1A H 0.1788 -0.1173 0.8279 0.119 Uiso 1 1 calc R . . H1B H 0.1136 -0.0806 0.8044 0.119 Uiso 1 1 calc R . . C2 C 0.1926(2) -0.0261(2) 0.7421(6) 0.0778(17) Uani 1 1 d . . . H2A H 0.1688 0.0084 0.7883 0.093 Uiso 1 1 calc R . . H2B H 0.234 -0.0297 0.7897 0.093 Uiso 1 1 calc R . . C3 C 0.2032(2) -0.00895(19) 0.5894(6) 0.0550(13) Uani 1 1 d . . . C4 C 0.15786(17) 0.02258(17) 0.5036(6) 0.0464(12) Uani 1 1 d . . . C5 C 0.15735(17) 0.00806(17) 0.3596(6) 0.0472(12) Uani 1 1 d . . . C6 C 0.20333(19) -0.03082(18) 0.2957(6) 0.0531(13) Uani 1 1 d . . . C7 C 0.2558(2) -0.04469(19) 0.3789(8) 0.0650(16) Uani 1 1 d . . . H7 H 0.2928 -0.0612 0.3361 0.078 Uiso 1 1 calc R . . C8 C 0.2548(2) -0.0348(2) 0.5217(8) 0.0649(16) Uani 1 1 d . . . H8 H 0.2908 -0.0462 0.5757 0.078 Uiso 1 1 calc R . . C9 C 0.1951(2) -0.0685(2) 0.1615(6) 0.0760(17) Uani 1 1 d . . . H9A H 0.2372 -0.0763 0.1198 0.091 Uiso 1 1 calc R . . H9B H 0.1705 -0.0429 0.0936 0.091 Uiso 1 1 calc R . . C10 C 0.1612(3) -0.1329(3) 0.1820(8) 0.113(2) Uani 1 1 d . . . H10A H 0.1211 -0.1323 0.1286 0.136 Uiso 1 1 calc R . . H10B H 0.1881 -0.1667 0.1419 0.136 Uiso 1 1 calc R . . C11 C 0.1472(3) -0.1485(2) 0.3325(8) 0.0798(19) Uani 1 1 d . . . C12 C 0.0939(2) -0.1255(2) 0.4002(8) 0.0734(18) Uani 1 1 d . . . H12 H 0.057 -0.1174 0.3462 0.088 Uiso 1 1 calc R . . C13 C 0.0924(2) -0.1138(2) 0.5436(7) 0.0676(16) Uani 1 1 d . . . H13 H 0.055 -0.0976 0.5851 0.081 Uiso 1 1 calc R . . C14 C 0.1449(2) -0.1256(2) 0.6277(7) 0.0725(16) Uani 1 1 d . . . C15 C 0.1917(2) -0.1628(2) 0.5661(10) 0.089(2) Uani 1 1 d . . . H15 H 0.2232 -0.1814 0.624 0.106 Uiso 1 1 calc R . . C16 C 0.1931(3) -0.1735(2) 0.4211(11) 0.096(3) Uani 1 1 d . . . H16 H 0.2261 -0.1984 0.3822 0.115 Uiso 1 1 calc R . . C17 C 0.0987(2) 0.0933(2) 0.1505(6) 0.0620(14) Uani 1 1 d . . . C18 C 0.0834(3) 0.1512(2) 0.2416(6) 0.0812(17) Uani 1 1 d . . . H18A H 0.0402 0.1475 0.2782 0.122 Uiso 1 1 calc R . . H18B H 0.0869 0.1895 0.1845 0.122 Uiso 1 1 calc R . . H18C H 0.1132 0.1534 0.3204 0.122 Uiso 1 1 calc R . . C19 C 0.1651(2) 0.0973(3) 0.0892(7) 0.095(2) Uani 1 1 d . . . H19A H 0.1733 0.0599 0.0312 0.143 Uiso 1 1 calc R . . H19B H 0.196 0.0991 0.166 0.143 Uiso 1 1 calc R . . H19C H 0.1688 0.1353 0.0312 0.143 Uiso 1 1 calc R . . C20 C 0.0490(3) 0.0873(3) 0.0328(6) 0.0973(19) Uani 1 1 d . . . H20A H 0.0068 0.0843 0.0747 0.146 Uiso 1 1 calc R . . H20B H 0.0575 0.0493 -0.0228 0.146 Uiso 1 1 calc R . . H20C H 0.0511 0.1245 -0.0283 0.146 Uiso 1 1 calc R . . C21 C 0.11325(18) 0.07125(18) 0.5692(5) 0.0518(12) Uani 1 1 d . . . H21 H 0.0848 0.0879 0.4938 0.062 Uiso 1 1 calc R . . C22 C 0.1487(2) 0.12722(19) 0.6357(6) 0.0628(14) Uani 1 1 d . . . H22 H 0.1672 0.1121 0.7266 0.075 Uiso 1 1 calc R . . C23 C 0.1006(3) 0.1790(2) 0.6710(7) 0.097(2) Uani 1 1 d . . . H23A H 0.0669 0.1612 0.7294 0.145 Uiso 1 1 calc R . . H23B H 0.0825 0.1957 0.5837 0.145 Uiso 1 1 calc R . . H23C H 0.1217 0.2131 0.7224 0.145 Uiso 1 1 calc R . . C24 C 0.2025(2) 0.1533(2) 0.5478(7) 0.0838(18) Uani 1 1 d . . . H24A H 0.2328 0.1195 0.5277 0.126 Uiso 1 1 calc R . . H24B H 0.2237 0.1872 0.5997 0.126 Uiso 1 1 calc R . . H24C H 0.1858 0.17 0.4591 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 S 0.0428(6) 0.0498(7) 0.0650(10) -0.0059(6) -0.0001(6) 0.0015(5) O1 0.0361(15) 0.0729(19) 0.078(3) -0.0052(19) 0.0020(16) 0.0008(13) O2 0.058(2) 0.083(2) 0.069(3) -0.013(2) 0.006(2) -0.0165(19) C1 0.115(5) 0.086(4) 0.096(6) 0.034(4) -0.006(4) -0.025(4) C2 0.068(3) 0.074(3) 0.091(5) 0.023(3) -0.013(3) -0.006(3) C3 0.046(3) 0.045(2) 0.074(4) 0.008(3) -0.009(3) -0.008(2) C4 0.037(2) 0.035(2) 0.068(4) 0.003(2) 0.000(2) -0.0069(18) C5 0.037(2) 0.034(2) 0.071(4) 0.000(2) 0.002(2) 0.0002(18) C6 0.042(2) 0.036(2) 0.082(4) -0.002(2) 0.015(3) -0.0031(19) C7 0.037(3) 0.040(3) 0.118(6) -0.002(3) 0.008(3) 0.003(2) C8 0.038(3) 0.042(2) 0.115(6) 0.009(3) -0.011(3) -0.004(2) C9 0.066(3) 0.057(3) 0.104(5) -0.026(3) 0.020(3) 0.005(2) C10 0.147(6) 0.072(4) 0.120(7) -0.030(4) 0.043(5) -0.033(4) C11 0.077(4) 0.034(3) 0.128(7) -0.016(3) 0.018(4) -0.007(3) C12 0.054(3) 0.042(3) 0.124(6) -0.004(3) -0.004(4) -0.015(2) C13 0.048(3) 0.047(3) 0.108(5) 0.008(3) 0.017(3) -0.007(2) C14 0.064(3) 0.051(3) 0.102(5) 0.020(3) 0.000(4) -0.010(3) C15 0.049(3) 0.044(3) 0.172(8) 0.032(4) -0.011(4) -0.002(3) C16 0.071(4) 0.036(3) 0.181(8) -0.008(4) 0.036(5) -0.002(3) C17 0.059(3) 0.062(3) 0.064(4) 0.008(3) 0.006(3) 0.008(2) C18 0.100(4) 0.054(3) 0.090(5) 0.010(3) -0.007(4) 0.014(3) C19 0.089(4) 0.086(4) 0.111(6) 0.033(4) 0.037(4) 0.011(3) C20 0.119(5) 0.107(4) 0.066(5) 0.008(4) -0.025(4) 0.007(4) C21 0.045(2) 0.048(2) 0.062(4) -0.002(2) 0.006(2) 0.001(2) C22 0.074(3) 0.052(3) 0.063(4) -0.006(3) 0.000(3) -0.006(2) C23 0.122(5) 0.062(3) 0.107(6) -0.030(3) 0.002(4) 0.011(3) C24 0.088(4) 0.062(3) 0.101(5) 0.000(3) -0.015(4) -0.023(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S O1 1.504(3) . ? S C5 1.811(4) . ? S C17 1.857(5) . ? O2 C21 1.422(5) . ? O2 H2X 0.86(4) . ? C1 C14 1.493(8) . ? C1 C2 1.579(7) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.512(7) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C8 1.381(7) . ? C3 C4 1.426(6) . ? C4 C5 1.403(6) . ? C4 C21 1.530(6) . ? C5 C6 1.412(6) . ? C6 C7 1.395(7) . ? C6 C9 1.514(7) . ? C7 C8 1.373(7) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C10 1.551(7) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.497(9) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.388(7) . ? C11 C16 1.390(9) . ? C12 C13 1.385(7) . ? C12 H12 0.95 . ? C13 C14 1.392(7) . ? C13 H13 0.95 . ? C14 C15 1.395(8) . ? C15 C16 1.396(9) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 C19 1.525(6) . ? C17 C18 1.535(7) . ? C17 C20 1.539(7) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 C22 1.539(6) . ? C21 H21 1 . ? C22 C24 1.517(7) . ? C22 C23 1.534(6) . ? C22 H22 1 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S C5 109.2(2) . . ? O1 S C17 105.82(19) . . ? C5 S C17 107.5(2) . . ? C21 O2 H2X 106(3) . . ? C14 C1 C2 113.9(5) . . ? C14 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? C14 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 113.1(5) . . ? C3 C2 H2A 109 . . ? C1 C2 H2A 109 . . ? C3 C2 H2B 109 . . ? C1 C2 H2B 109 . . ? H2A C2 H2B 107.8 . . ? C8 C3 C4 116.9(5) . . ? C8 C3 C2 118.0(5) . . ? C4 C3 C2 124.1(4) . . ? C5 C4 C3 117.4(4) . . ? C5 C4 C21 122.7(4) . . ? C3 C4 C21 119.9(5) . . ? C4 C5 C6 122.8(4) . . ? C4 C5 S 122.7(3) . . ? C6 C5 S 112.5(4) . . ? C7 C6 C5 115.3(5) . . ? C7 C6 C9 117.3(4) . . ? C5 C6 C9 126.1(4) . . ? C8 C7 C6 121.1(5) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C3 122.2(5) . . ? C7 C8 H8 118.9 . . ? C3 C8 H8 118.9 . . ? C6 C9 C10 114.3(5) . . ? C6 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? C6 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C9 113.9(5) . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C16 114.9(7) . . ? C12 C11 C10 121.7(6) . . ? C16 C11 C10 121.6(6) . . ? C13 C12 C11 122.4(6) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C12 C13 C14 121.1(5) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C15 115.3(6) . . ? C13 C14 C1 121.0(5) . . ? C15 C14 C1 122.6(6) . . ? C14 C15 C16 121.4(6) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C11 C16 C15 121.4(6) . . ? C11 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C19 C17 C18 111.4(4) . . ? C19 C17 C20 110.9(5) . . ? C18 C17 C20 109.4(4) . . ? C19 C17 S 110.6(3) . . ? C18 C17 S 111.5(4) . . ? C20 C17 S 102.6(3) . . ? 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 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 C21 C4 112.7(3) . . ? O2 C21 C22 105.9(4) . . ? C4 C21 C22 112.6(3) . . ? O2 C21 H21 108.5 . . ? C4 C21 H21 108.5 . . ? C22 C21 H21 108.5 . . ? C24 C22 C23 111.1(4) . . ? C24 C22 C21 114.9(4) . . ? C23 C22 C21 108.4(4) . . ? C24 C22 H22 107.4 . . ? C23 C22 H22 107.4 . . ? C21 C22 H22 107.4 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? #===END