Electronic Supplementary Material for CrystEngComm. This journal is © The Royal Society of Chemistry 2004. data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Louis Farrugia' 'Laura Ballie' 'D. MacNicol' 'Ross MacSween' _publ_contact_author_name 'Dr Louis Farrugia' _publ_contact_author_address ; Department of Chemistry University of Glasgow University Avenue Glasgow G12 8QQ UNITED KINGDOM ; _publ_contact_author_email LOUIS@CHEM.GLA.AC.UK _publ_requested_journal Cryst.Eng.Comm. _publ_section_title ; 2,7-Di-p-chlorobenzoylnaphtho[2'3'-4:5]thiepin: A conformationally flexible new host molecule showing solvatochromic effects. ; data_dioxane-clathrate _database_code_depnum_ccdc_archive 'CCDC 239491' _audit_creation_date 2004-02-16T18:07:52-00:00 _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 'C28 H16 Cl2 O2 S, C4 H8 O2' _chemical_formula_sum 'C32 H24 Cl2 O4 S' _chemical_formula_weight 575.47 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.2438(3) _cell_length_b 14.3080(2) _cell_length_c 19.1313(3) _cell_angle_alpha 90 _cell_angle_beta 105.6880(10) _cell_angle_gamma 90 _cell_volume 5334.92(14) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7908 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 30.034 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.129 -1 0 0 0.179 -1 -1 1 0.13 1 1 -1 0.13 1 -1 1 0.1 -1 1 -1 0.14 1 1 1 0.15 -1 -1 -1 0.15 -1 1 1 0.15 1 -1 -1 0.1 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.36 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst. (1965), 18, 1035-1038 ; _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.938 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(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 -0.150562E-1 _diffrn_orient_matrix_ub_12 0.244974E-1 _diffrn_orient_matrix_ub_13 0.421815E-1 _diffrn_orient_matrix_ub_21 0.488382E-1 _diffrn_orient_matrix_ub_22 0.135266E-1 _diffrn_orient_matrix_ub_23 0.264017E-1 _diffrn_orient_matrix_ub_31 -0.45559E-2 _diffrn_orient_matrix_ub_32 0.640442E-1 _diffrn_orient_matrix_ub_33 -0.21711E-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 0.0324 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_number 46956 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 30.04 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 7807 _reflns_number_gt 6885 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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^)+(0.0377P)^2^+5.6181P] 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 7807 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.083 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.416 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 C2 C 0.03380(5) 0.15127(8) 0.16218(6) 0.01557(19) Uani 1 1 d . . . C3 C -0.02448(6) 0.20234(8) 0.14503(6) 0.01621(19) Uani 1 1 d . . . H3 H -0.0646 0.1665 0.1247 0.019 Uiso 1 1 calc R . . C4 C -0.03822(5) 0.30216(7) 0.15155(5) 0.01432(19) Uani 1 1 d . . . C5 C 0.00994(5) 0.37717(7) 0.15548(5) 0.01343(18) Uani 1 1 d . . . C6 C 0.08149(5) 0.36903(7) 0.15379(5) 0.01391(19) Uani 1 1 d . . . H6 H 0.0993 0.4246 0.1386 0.017 Uiso 1 1 calc R . . C7 C 0.12739(5) 0.29846(7) 0.16939(5) 0.01330(18) Uani 1 1 d . . . C8 C -0.01202(5) 0.46821(8) 0.15945(5) 0.01483(19) Uani 1 1 d . . . H8 H 0.0192 0.5178 0.1596 0.018 Uiso 1 1 calc R . . C9 C -0.07917(6) 0.49052(8) 0.16329(5) 0.0160(2) Uani 1 1 d . . . C10 C -0.09987(6) 0.58389(8) 0.17079(6) 0.0210(2) Uani 1 1 d . . . H10 H -0.0685 0.6338 0.1727 0.025 Uiso 1 1 calc R . . C11 C -0.16529(7) 0.60218(9) 0.17524(7) 0.0254(3) Uani 1 1 d . . . H11 H -0.1788 0.6648 0.1804 0.03 Uiso 1 1 calc R . . C12 C -0.21250(6) 0.52874(10) 0.17224(7) 0.0254(3) Uani 1 1 d . . . H12 H -0.2575 0.5423 0.1756 0.03 Uiso 1 1 calc R . . C13 C -0.19391(6) 0.43784(9) 0.16451(6) 0.0213(2) Uani 1 1 d . . . H13 H -0.2261 0.3889 0.1622 0.026 Uiso 1 1 calc R . . C14 C -0.12655(6) 0.41666(8) 0.15990(6) 0.0162(2) Uani 1 1 d . . . C15 C -0.10474(6) 0.32387(8) 0.15209(6) 0.0164(2) Uani 1 1 d . . . H15 H -0.1371 0.2746 0.147 0.02 Uiso 1 1 calc R . . C16 C 0.02901(6) 0.04665(8) 0.16369(6) 0.0184(2) Uani 1 1 d . . . C17 C -0.02933(6) -0.00465(7) 0.11412(6) 0.0171(2) Uani 1 1 d . . . C18 C -0.05133(6) -0.08762(8) 0.13957(6) 0.0201(2) Uani 1 1 d . . . H18 H -0.0313 -0.1069 0.1882 0.024 Uiso 1 1 calc R . . C19 C -0.10184(6) -0.14180(8) 0.09458(7) 0.0202(2) Uani 1 1 d . . . H19 H -0.1177 -0.197 0.1123 0.024 Uiso 1 1 calc R . . C20 C -0.12894(6) -0.11399(8) 0.02288(6) 0.0182(2) Uani 1 1 d . . . C21 C -0.10760(6) -0.03278(8) -0.00394(6) 0.0188(2) Uani 1 1 d . . . H21 H -0.1264 -0.0153 -0.0532 0.023 Uiso 1 1 calc R . . C22 C -0.05824(6) 0.02284(8) 0.04232(6) 0.0181(2) Uani 1 1 d . . . H22 H -0.0442 0.0796 0.025 0.022 Uiso 1 1 calc R . . C23 C 0.20122(5) 0.32069(7) 0.17755(5) 0.01390(19) Uani 1 1 d . . . C24 C 0.22051(5) 0.40108(7) 0.13726(6) 0.01404(19) Uani 1 1 d . . . C25 C 0.18639(6) 0.42025(8) 0.06483(6) 0.0160(2) Uani 1 1 d . . . H25 H 0.1486 0.3826 0.0402 0.019 Uiso 1 1 calc R . . C26 C 0.20743(6) 0.49397(8) 0.02868(6) 0.0173(2) Uani 1 1 d . . . H26 H 0.1852 0.5061 -0.0209 0.021 Uiso 1 1 calc R . . C27 C 0.26156(6) 0.54956(8) 0.06649(6) 0.0171(2) Uani 1 1 d . . . C28 C 0.29642(6) 0.53194(8) 0.13838(6) 0.0181(2) Uani 1 1 d . . . H28 H 0.3333 0.5709 0.1633 0.022 Uiso 1 1 calc R . . C29 C 0.27633(5) 0.45637(8) 0.17318(6) 0.0166(2) Uani 1 1 d . . . H29 H 0.3007 0.4421 0.2218 0.02 Uiso 1 1 calc R . . Cl1 Cl -0.191760(15) -0.18281(2) -0.033600(16) 0.02395(7) Uani 1 1 d . . . Cl2 Cl 0.285460(16) 0.64530(2) 0.022744(17) 0.02412(7) Uani 1 1 d . . . O30 O 0.24565(4) 0.27449(6) 0.21983(4) 0.01924(16) Uani 1 1 d . . . O31 O 0.07421(5) 0.00326(6) 0.20717(5) 0.0275(2) Uani 1 1 d . . . S1 S 0.120404(13) 0.183308(18) 0.199673(14) 0.01573(6) Uani 1 1 d . . . C33 C 0.48383(7) 0.21502(10) 0.46187(7) 0.0292(3) Uani 1 1 d . . . H33A H 0.5128 0.2269 0.5117 0.035 Uiso 1 1 calc R . . H33B H 0.5145 0.2055 0.43 0.035 Uiso 1 1 calc R . . C34 C 0.44126(8) 0.12828(10) 0.46143(7) 0.0300(3) Uani 1 1 d . . . H34A H 0.4719 0.0741 0.4782 0.036 Uiso 1 1 calc R . . H34B H 0.4124 0.1366 0.4953 0.036 Uiso 1 1 calc R . . C36 C 0.35457(7) 0.18894(9) 0.36632(7) 0.0272(3) Uani 1 1 d . . . H36A H 0.3247 0.1983 0.3991 0.033 Uiso 1 1 calc R . . H36B H 0.3248 0.177 0.3168 0.033 Uiso 1 1 calc R . . C37 C 0.39688(8) 0.27558(10) 0.36596(8) 0.0331(3) Uani 1 1 d . . . H37A H 0.4251 0.2673 0.3314 0.04 Uiso 1 1 calc R . . H37B H 0.3661 0.3297 0.3497 0.04 Uiso 1 1 calc R . . O32 O 0.44073(6) 0.29341(7) 0.43722(6) 0.0334(2) Uani 1 1 d . . . O35 O 0.39862(5) 0.11047(6) 0.39031(5) 0.02682(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0160(5) 0.0133(5) 0.0170(5) 0.0017(4) 0.0038(4) 0.0001(4) C3 0.0155(5) 0.0147(5) 0.0185(5) 0.0010(4) 0.0047(4) 0.0001(4) C4 0.0138(5) 0.0150(5) 0.0140(4) 0.0017(3) 0.0034(3) 0.0018(4) C5 0.0131(4) 0.0144(5) 0.0124(4) 0.0000(3) 0.0029(3) 0.0020(4) C6 0.0143(5) 0.0141(5) 0.0132(4) -0.0004(3) 0.0034(3) 0.0007(4) C7 0.0137(4) 0.0135(4) 0.0126(4) 0.0002(3) 0.0034(3) 0.0004(4) C8 0.0148(5) 0.0149(5) 0.0142(4) 0.0002(3) 0.0029(3) 0.0027(4) C9 0.0172(5) 0.0177(5) 0.0128(4) 0.0012(4) 0.0037(4) 0.0052(4) C10 0.0226(6) 0.0191(5) 0.0213(5) 0.0008(4) 0.0061(4) 0.0071(4) C11 0.0280(6) 0.0253(6) 0.0245(6) 0.0029(5) 0.0100(5) 0.0136(5) C12 0.0216(6) 0.0338(7) 0.0240(5) 0.0080(5) 0.0116(4) 0.0136(5) C13 0.0174(5) 0.0282(6) 0.0207(5) 0.0083(4) 0.0092(4) 0.0068(4) C14 0.0149(5) 0.0210(5) 0.0134(4) 0.0042(4) 0.0050(4) 0.0054(4) C15 0.0144(5) 0.0188(5) 0.0162(5) 0.0034(4) 0.0044(4) 0.0020(4) C16 0.0190(5) 0.0135(5) 0.0226(5) 0.0018(4) 0.0053(4) 0.0007(4) C17 0.0179(5) 0.0120(5) 0.0219(5) 0.0005(4) 0.0060(4) 0.0013(4) C18 0.0234(5) 0.0145(5) 0.0226(5) 0.0029(4) 0.0065(4) 0.0015(4) C19 0.0233(5) 0.0123(5) 0.0272(6) 0.0007(4) 0.0106(4) -0.0008(4) C20 0.0179(5) 0.0140(5) 0.0242(5) -0.0046(4) 0.0083(4) -0.0003(4) C21 0.0203(5) 0.0174(5) 0.0196(5) 0.0002(4) 0.0071(4) 0.0016(4) C22 0.0194(5) 0.0135(5) 0.0229(5) 0.0022(4) 0.0085(4) 0.0009(4) C23 0.0137(4) 0.0135(4) 0.0144(4) -0.0022(3) 0.0035(3) 0.0018(4) C24 0.0119(4) 0.0143(5) 0.0163(4) -0.0012(4) 0.0045(3) 0.0022(4) C25 0.0145(5) 0.0156(5) 0.0170(5) -0.0017(4) 0.0030(4) 0.0001(4) C26 0.0176(5) 0.0170(5) 0.0169(5) 0.0007(4) 0.0038(4) 0.0022(4) C27 0.0177(5) 0.0129(5) 0.0225(5) 0.0008(4) 0.0085(4) 0.0016(4) C28 0.0154(5) 0.0170(5) 0.0219(5) -0.0039(4) 0.0049(4) -0.0018(4) C29 0.0141(5) 0.0189(5) 0.0160(4) -0.0019(4) 0.0027(4) 0.0007(4) Cl1 0.02416(14) 0.01938(13) 0.02910(14) -0.00766(10) 0.00857(11) -0.00461(10) Cl2 0.02631(14) 0.01551(13) 0.03151(15) 0.00507(10) 0.00950(11) -0.00078(10) O30 0.0159(4) 0.0186(4) 0.0214(4) 0.0026(3) 0.0020(3) 0.0042(3) O31 0.0244(4) 0.0173(4) 0.0350(5) 0.0070(3) -0.0020(4) 0.0013(3) S1 0.01433(12) 0.01342(12) 0.01849(12) 0.00329(9) 0.00281(9) 0.00215(9) C33 0.0300(7) 0.0315(7) 0.0249(6) -0.0022(5) 0.0055(5) -0.0048(5) C34 0.0397(7) 0.0259(6) 0.0199(5) 0.0042(5) 0.0003(5) -0.0029(5) C36 0.0265(6) 0.0246(6) 0.0288(6) 0.0037(5) 0.0048(5) -0.0001(5) C37 0.0350(7) 0.0224(6) 0.0400(7) 0.0092(5) 0.0069(6) -0.0001(5) O32 0.0395(6) 0.0209(5) 0.0411(5) -0.0073(4) 0.0130(4) -0.0051(4) O35 0.0365(5) 0.0182(4) 0.0223(4) -0.0008(3) 0.0021(4) 0.0007(4) #----------------------------------------------------------------------------# # 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 C2 C3 1.3506(15) . ? C2 C16 1.5008(15) . ? C2 S1 1.7659(11) . ? C3 C4 1.4669(15) . ? C3 H3 0.95 . ? C4 C15 1.3847(15) . ? C4 C5 1.4381(15) . ? C5 C8 1.3850(14) . ? C5 C6 1.4623(14) . ? C6 C7 1.3498(14) . ? C6 H6 0.95 . ? C7 C23 1.4943(14) . ? C7 S1 1.7648(11) . ? C8 C9 1.4175(15) . ? C8 H8 0.95 . ? C9 C14 1.4168(16) . ? C9 C10 1.4188(15) . ? C10 C11 1.3752(17) . ? C10 H10 0.95 . ? C11 C12 1.411(2) . ? C11 H11 0.95 . ? C12 C13 1.3730(18) . ? C12 H12 0.95 . ? C13 C14 1.4227(15) . ? C13 H13 0.95 . ? C14 C15 1.4197(15) . ? C15 H15 0.95 . ? C16 O31 1.2260(14) . ? C16 C17 1.4924(16) . ? C17 C22 1.3962(15) . ? C17 C18 1.4007(15) . ? C18 C19 1.3824(16) . ? C18 H18 0.95 . ? C19 C20 1.3906(16) . ? C19 H19 0.95 . ? C20 C21 1.3858(16) . ? C20 Cl1 1.7352(11) . ? C21 C22 1.3917(16) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? C23 O30 1.2275(13) . ? C23 C24 1.4942(15) . ? C24 C25 1.3981(14) . ? C24 C29 1.3983(15) . ? C25 C26 1.3898(15) . ? C25 H25 0.95 . ? C26 C27 1.3884(16) . ? C26 H26 0.95 . ? C27 C28 1.3887(16) . ? C27 Cl2 1.7407(11) . ? C28 C29 1.3871(16) . ? C28 H28 0.95 . ? C29 H29 0.95 . ? C33 O32 1.4209(18) . ? C33 C34 1.5097(19) . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C34 O35 1.4234(15) . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C36 O35 1.4301(16) . ? C36 C37 1.5078(19) . ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? C37 O32 1.4342(18) . ? C37 H37A 0.99 . ? C37 H37B 0.99 . ? 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 C3 C2 C16 119.18(10) . . ? C3 C2 S1 131.63(9) . . ? C16 C2 S1 108.26(8) . . ? C2 C3 C4 132.80(10) . . ? C2 C3 H3 113.6 . . ? C4 C3 H3 113.6 . . ? C15 C4 C5 118.62(10) . . ? C15 C4 C3 115.23(10) . . ? C5 C4 C3 126.13(9) . . ? C8 C5 C4 118.79(10) . . ? C8 C5 C6 114.24(9) . . ? C4 C5 C6 126.94(9) . . ? C7 C6 C5 132.96(10) . . ? C7 C6 H6 113.5 . . ? C5 C6 H6 113.5 . . ? C6 C7 C23 118.24(9) . . ? C6 C7 S1 131.26(8) . . ? C23 C7 S1 109.34(7) . . ? C5 C8 C9 122.76(10) . . ? C5 C8 H8 118.6 . . ? C9 C8 H8 118.6 . . ? C14 C9 C8 118.45(10) . . ? C14 C9 C10 119.48(10) . . ? C8 C9 C10 122.07(11) . . ? C11 C10 C9 120.08(12) . . ? C11 C10 H10 120 . . ? C9 C10 H10 120 . . ? C10 C11 C12 120.58(12) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 120.50(11) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.24(12) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C9 C14 C15 118.45(10) . . ? C9 C14 C13 119.12(10) . . ? C15 C14 C13 122.43(11) . . ? C4 C15 C14 122.78(10) . . ? C4 C15 H15 118.6 . . ? C14 C15 H15 118.6 . . ? O31 C16 C17 119.95(10) . . ? O31 C16 C2 118.55(10) . . ? C17 C16 C2 121.50(9) . . ? C22 C17 C18 119.51(10) . . ? C22 C17 C16 122.40(10) . . ? C18 C17 C16 117.86(10) . . ? C19 C18 C17 120.67(11) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 118.80(10) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C21 C20 C19 121.72(10) . . ? C21 C20 Cl1 119.64(9) . . ? C19 C20 Cl1 118.63(9) . . ? C20 C21 C22 119.08(10) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C21 C22 C17 120.17(10) . . ? C21 C22 H22 119.9 . . ? C17 C22 H22 119.9 . . ? O30 C23 C24 120.49(10) . . ? O30 C23 C7 119.22(10) . . ? C24 C23 C7 120.23(9) . . ? C25 C24 C29 119.55(10) . . ? C25 C24 C23 122.30(9) . . ? C29 C24 C23 118.11(9) . . ? C26 C25 C24 120.41(10) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C27 C26 C25 118.72(10) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? C26 C27 C28 122.01(10) . . ? C26 C27 Cl2 118.89(9) . . ? C28 C27 Cl2 119.09(9) . . ? C29 C28 C27 118.71(10) . . ? C29 C28 H28 120.6 . . ? C27 C28 H28 120.6 . . ? C28 C29 C24 120.53(10) . . ? C28 C29 H29 119.7 . . ? C24 C29 H29 119.7 . . ? C7 S1 C2 105.54(5) . . ? O32 C33 C34 110.41(11) . . ? O32 C33 H33A 109.6 . . ? C34 C33 H33A 109.6 . . ? O32 C33 H33B 109.6 . . ? C34 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? O35 C34 C33 110.51(10) . . ? O35 C34 H34A 109.5 . . ? C33 C34 H34A 109.5 . . ? O35 C34 H34B 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 108.1 . . ? O35 C36 C37 109.96(11) . . ? O35 C36 H36A 109.7 . . ? C37 C36 H36A 109.7 . . ? O35 C36 H36B 109.7 . . ? C37 C36 H36B 109.7 . . ? H36A C36 H36B 108.2 . . ? O32 C37 C36 110.38(11) . . ? O32 C37 H37A 109.6 . . ? C36 C37 H37A 109.6 . . ? O32 C37 H37B 109.6 . . ? C36 C37 H37B 109.6 . . ? H37A C37 H37B 108.1 . . ? C33 O32 C37 109.99(10) . . ? C34 O35 C36 109.30(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C2 C3 C4 166.74(11) . . . . ? S1 C2 C3 C4 -0.8(2) . . . . ? C2 C3 C4 C15 -158.44(12) . . . . ? C2 C3 C4 C5 23.17(19) . . . . ? C15 C4 C5 C8 -0.18(14) . . . . ? C3 C4 C5 C8 178.16(10) . . . . ? C15 C4 C5 C6 -178.34(10) . . . . ? C3 C4 C5 C6 0.00(17) . . . . ? C8 C5 C6 C7 159.12(11) . . . . ? C4 C5 C6 C7 -22.65(18) . . . . ? C5 C6 C7 C23 -166.55(10) . . . . ? C5 C6 C7 S1 -0.37(18) . . . . ? C4 C5 C8 C9 3.09(15) . . . . ? C6 C5 C8 C9 -178.52(9) . . . . ? C5 C8 C9 C14 -2.67(15) . . . . ? C5 C8 C9 C10 176.96(10) . . . . ? C14 C9 C10 C11 0.47(16) . . . . ? C8 C9 C10 C11 -179.16(10) . . . . ? C9 C10 C11 C12 -0.16(18) . . . . ? C10 C11 C12 C13 -0.28(18) . . . . ? C11 C12 C13 C14 0.40(18) . . . . ? C8 C9 C14 C15 -0.62(14) . . . . ? C10 C9 C14 C15 179.74(10) . . . . ? C8 C9 C14 C13 179.29(10) . . . . ? C10 C9 C14 C13 -0.35(15) . . . . ? C12 C13 C14 C9 -0.08(16) . . . . ? C12 C13 C14 C15 179.82(11) . . . . ? C5 C4 C15 C14 -3.14(15) . . . . ? C3 C4 C15 C14 178.34(10) . . . . ? C9 C14 C15 C4 3.54(15) . . . . ? C13 C14 C15 C4 -176.36(10) . . . . ? C3 C2 C16 O31 -147.73(12) . . . . ? S1 C2 C16 O31 22.49(14) . . . . ? C3 C2 C16 C17 31.88(16) . . . . ? S1 C2 C16 C17 -157.90(9) . . . . ? O31 C16 C17 C22 -142.46(12) . . . . ? C2 C16 C17 C22 37.94(16) . . . . ? O31 C16 C17 C18 32.06(16) . . . . ? C2 C16 C17 C18 -147.54(11) . . . . ? C22 C17 C18 C19 -0.74(17) . . . . ? C16 C17 C18 C19 -175.43(11) . . . . ? C17 C18 C19 C20 1.98(18) . . . . ? C18 C19 C20 C21 -1.29(17) . . . . ? C18 C19 C20 Cl1 179.41(9) . . . . ? C19 C20 C21 C22 -0.65(17) . . . . ? Cl1 C20 C21 C22 178.65(9) . . . . ? C20 C21 C22 C17 1.90(17) . . . . ? C18 C17 C22 C21 -1.23(17) . . . . ? C16 C17 C22 C21 173.21(10) . . . . ? C6 C7 C23 O30 148.49(10) . . . . ? S1 C7 C23 O30 -20.53(12) . . . . ? C6 C7 C23 C24 -28.68(14) . . . . ? S1 C7 C23 C24 162.30(8) . . . . ? O30 C23 C24 C25 140.89(11) . . . . ? C7 C23 C24 C25 -41.98(14) . . . . ? O30 C23 C24 C29 -36.74(15) . . . . ? C7 C23 C24 C29 140.39(10) . . . . ? C29 C24 C25 C26 -0.31(16) . . . . ? C23 C24 C25 C26 -177.91(10) . . . . ? C24 C25 C26 C27 -1.81(16) . . . . ? C25 C26 C27 C28 1.98(17) . . . . ? C25 C26 C27 Cl2 -176.98(8) . . . . ? C26 C27 C28 C29 0.02(17) . . . . ? Cl2 C27 C28 C29 178.99(8) . . . . ? C27 C28 C29 C24 -2.21(16) . . . . ? C25 C24 C29 C28 2.37(16) . . . . ? C23 C24 C29 C28 -179.93(10) . . . . ? C6 C7 S1 C2 31.00(12) . . . . ? C23 C7 S1 C2 -161.89(7) . . . . ? C3 C2 S1 C7 -30.49(12) . . . . ? C16 C2 S1 C7 160.96(7) . . . . ? O32 C33 C34 O35 58.60(15) . . . . ? O35 C36 C37 O32 -58.81(15) . . . . ? C34 C33 O32 C37 -57.25(14) . . . . ? C36 C37 O32 C33 57.68(15) . . . . ? C33 C34 O35 C36 -59.10(15) . . . . ? C37 C36 O35 C34 59.21(14) . . . . ? data_benzene-clathrate _database_code_depnum_ccdc_archive 'CCDC 239492' _audit_creation_date 2004-02-27T17:15:42-00:00 _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 'C28 H16 Cl2 O2 S, 0.5(C6 H6)' _chemical_formula_sum 'C31 H19 Cl2 O2 S' _chemical_formula_weight 526.42 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.3796(10) _cell_length_b 10.1112(2) _cell_length_c 14.2492(4) _cell_angle_alpha 90 _cell_angle_beta 91.1170(10) _cell_angle_gamma 90 _cell_volume 4808.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12248 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 29.987 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.386 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 0.973 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(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 0.180302E-1 _diffrn_orient_matrix_ub_12 0.789918E-1 _diffrn_orient_matrix_ub_13 0.7987E-3 _diffrn_orient_matrix_ub_21 -0.200432E-1 _diffrn_orient_matrix_ub_22 0.498637E-1 _diffrn_orient_matrix_ub_23 0.374187E-1 _diffrn_orient_matrix_ub_31 0.130778E-1 _diffrn_orient_matrix_ub_32 -0.324834E-1 _diffrn_orient_matrix_ub_33 0.59382E-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 0.0387 _diffrn_reflns_av_unetI/netI 0.0287 _diffrn_reflns_number 38910 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 30.03 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 7011 _reflns_number_gt 5746 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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^)+(0.0333P)^2^+5.6272P] 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 7011 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.362 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.051 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 C2 C 0.23075(4) 0.36036(12) 0.31790(8) 0.0166(2) Uani 1 1 d . . . C3 C 0.26120(4) 0.41863(12) 0.36568(9) 0.0169(2) Uani 1 1 d . . . H3 H 0.256 0.5052 0.3883 0.02 Uiso 1 1 calc R . . C4 C 0.30122(4) 0.36644(12) 0.38736(8) 0.0166(2) Uani 1 1 d . . . C5 C 0.30937(4) 0.23127(12) 0.41314(9) 0.0177(2) Uani 1 1 d . . . C6 C 0.27893(4) 0.12788(12) 0.42330(9) 0.0179(2) Uani 1 1 d . . . H6 H 0.2831 0.069 0.4745 0.021 Uiso 1 1 calc R . . C7 C 0.24599(4) 0.10518(12) 0.37002(9) 0.0168(2) Uani 1 1 d . . . C8 C 0.34831(4) 0.19605(13) 0.43762(9) 0.0204(2) Uani 1 1 d . . . H8 H 0.3534 0.1082 0.4582 0.024 Uiso 1 1 calc R . . C9 C 0.38069(4) 0.28529(13) 0.43318(9) 0.0202(2) Uani 1 1 d . . . C10 C 0.42080(4) 0.24621(15) 0.45376(10) 0.0260(3) Uani 1 1 d . . . H10 H 0.4266 0.1564 0.4681 0.031 Uiso 1 1 calc R . . C11 C 0.45125(4) 0.33739(16) 0.45308(11) 0.0290(3) Uani 1 1 d . . . H11 H 0.4779 0.3105 0.4674 0.035 Uiso 1 1 calc R . . C12 C 0.44301(4) 0.47104(16) 0.43116(11) 0.0286(3) Uani 1 1 d . . . H12 H 0.4643 0.5336 0.4312 0.034 Uiso 1 1 calc R . . C13 C 0.40479(4) 0.51133(14) 0.40989(10) 0.0243(3) Uani 1 1 d . . . H13 H 0.3997 0.6014 0.3948 0.029 Uiso 1 1 calc R . . C14 C 0.37254(4) 0.41942(13) 0.41015(9) 0.0193(2) Uani 1 1 d . . . C15 C 0.33255(4) 0.45708(13) 0.38986(9) 0.0187(2) Uani 1 1 d . . . H15 H 0.3269 0.5475 0.3775 0.022 Uiso 1 1 calc R . . C16 C 0.19144(4) 0.43246(12) 0.31019(9) 0.0182(2) Uani 1 1 d . . . C17 C 0.16270(4) 0.40509(13) 0.23067(9) 0.0184(2) Uani 1 1 d . . . C18 C 0.12227(4) 0.43450(14) 0.24436(10) 0.0231(3) Uani 1 1 d . . . H18 H 0.114 0.467 0.3034 0.028 Uiso 1 1 calc R . . C19 C 0.09418(4) 0.41654(15) 0.17229(10) 0.0253(3) Uani 1 1 d . . . H19 H 0.0667 0.4356 0.1817 0.03 Uiso 1 1 calc R . . C20 C 0.10698(4) 0.37039(13) 0.08665(10) 0.0225(3) Uani 1 1 d . . . C21 C 0.14688(4) 0.34154(13) 0.07033(10) 0.0218(3) Uani 1 1 d . . . H21 H 0.155 0.3108 0.0106 0.026 Uiso 1 1 calc R . . C22 C 0.17470(4) 0.35859(13) 0.14327(9) 0.0189(2) Uani 1 1 d . . . H22 H 0.2021 0.3384 0.1336 0.023 Uiso 1 1 calc R . . C23 C 0.22071(4) -0.01419(12) 0.39188(9) 0.0176(2) Uani 1 1 d . . . C24 C 0.17772(4) -0.02337(13) 0.36131(9) 0.0176(2) Uani 1 1 d . . . C25 C 0.16215(4) -0.14967(13) 0.34351(9) 0.0218(3) Uani 1 1 d . . . H25 H 0.1795 -0.2241 0.344 0.026 Uiso 1 1 calc R . . C26 C 0.12156(4) -0.16679(14) 0.32513(10) 0.0254(3) Uani 1 1 d . . . H26 H 0.1111 -0.2521 0.3113 0.03 Uiso 1 1 calc R . . C27 C 0.09651(4) -0.05736(15) 0.32720(10) 0.0249(3) Uani 1 1 d . . . C28 C 0.11119(4) 0.06880(15) 0.34258(10) 0.0246(3) Uani 1 1 d . . . H28 H 0.0936 0.1428 0.3419 0.029 Uiso 1 1 calc R . . C29 C 0.15214(4) 0.08560(13) 0.35908(9) 0.0210(3) Uani 1 1 d . . . H29 H 0.1627 0.1719 0.3689 0.025 Uiso 1 1 calc R . . Cl1 Cl 0.071611(11) 0.35041(4) -0.00404(3) 0.03514(10) Uani 1 1 d . . . Cl2 Cl 0.044990(10) -0.07979(4) 0.31235(3) 0.03588(10) Uani 1 1 d . . . O30 O 0.23572(3) -0.10572(10) 0.43632(7) 0.0249(2) Uani 1 1 d . . . O31 O 0.18279(3) 0.51335(10) 0.37048(7) 0.0267(2) Uani 1 1 d . . . S1 S 0.235269(9) 0.19974(3) 0.26769(2) 0.01762(7) Uani 1 1 d . . . C32 C 0.00781(5) 0.30112(17) 0.29542(13) 0.0381(4) Uani 1 1 d . . . H32 H 0.0132 0.2198 0.3265 0.046 Uiso 1 1 calc R . . C33 C 0.01552(5) 0.41985(18) 0.34087(12) 0.0351(4) Uani 1 1 d . . . H33 H 0.0261 0.42 0.4032 0.042 Uiso 1 1 calc R . . C34 C 0.00779(5) 0.53807(17) 0.29535(12) 0.0336(3) Uani 1 1 d . . . H34 H 0.0132 0.6195 0.3264 0.04 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 C2 0.0182(6) 0.0150(5) 0.0166(5) 0.0003(4) 0.0000(4) 0.0019(4) C3 0.0184(6) 0.0152(5) 0.0172(5) 0.0008(4) 0.0000(4) 0.0009(4) C4 0.0171(5) 0.0171(6) 0.0154(5) -0.0015(4) -0.0016(4) -0.0001(4) C5 0.0172(6) 0.0179(6) 0.0181(5) -0.0011(4) -0.0016(4) -0.0007(4) C6 0.0176(6) 0.0160(6) 0.0200(6) 0.0006(5) 0.0006(4) 0.0005(4) C7 0.0172(5) 0.0147(5) 0.0185(6) 0.0003(4) 0.0005(4) 0.0015(4) C8 0.0199(6) 0.0166(6) 0.0245(6) -0.0001(5) -0.0041(5) 0.0009(5) C9 0.0175(6) 0.0215(6) 0.0215(6) -0.0022(5) -0.0017(5) 0.0001(5) C10 0.0201(6) 0.0239(7) 0.0337(7) -0.0026(6) -0.0048(5) 0.0018(5) C11 0.0175(6) 0.0341(8) 0.0353(8) -0.0032(6) -0.0033(5) -0.0004(6) C12 0.0207(6) 0.0315(8) 0.0337(8) -0.0036(6) 0.0001(5) -0.0078(6) C13 0.0226(6) 0.0222(6) 0.0282(7) -0.0009(5) 0.0002(5) -0.0046(5) C14 0.0186(6) 0.0200(6) 0.0193(6) -0.0022(5) -0.0013(5) -0.0021(5) C15 0.0202(6) 0.0168(6) 0.0190(6) -0.0008(5) -0.0016(5) 0.0000(5) C16 0.0176(6) 0.0171(6) 0.0199(6) 0.0016(5) -0.0009(4) 0.0007(4) C17 0.0173(6) 0.0172(6) 0.0206(6) 0.0023(5) -0.0020(5) 0.0006(4) C18 0.0193(6) 0.0268(7) 0.0231(6) -0.0004(5) -0.0003(5) 0.0030(5) C19 0.0162(6) 0.0293(7) 0.0303(7) 0.0016(6) -0.0024(5) 0.0016(5) C20 0.0214(6) 0.0204(6) 0.0255(6) 0.0023(5) -0.0083(5) -0.0005(5) C21 0.0240(6) 0.0206(6) 0.0209(6) 0.0017(5) -0.0017(5) 0.0011(5) C22 0.0171(6) 0.0178(6) 0.0217(6) 0.0031(5) -0.0002(5) -0.0005(5) C23 0.0168(5) 0.0173(6) 0.0188(6) -0.0010(4) 0.0010(4) -0.0002(4) C24 0.0163(5) 0.0198(6) 0.0167(5) 0.0006(5) 0.0010(4) -0.0019(5) C25 0.0225(6) 0.0199(6) 0.0230(6) 0.0011(5) 0.0019(5) -0.0016(5) C26 0.0252(7) 0.0255(7) 0.0256(7) 0.0006(5) 0.0009(5) -0.0091(5) C27 0.0170(6) 0.0363(8) 0.0213(6) 0.0029(6) -0.0008(5) -0.0060(5) C28 0.0183(6) 0.0291(7) 0.0264(7) -0.0001(6) 0.0002(5) 0.0024(5) C29 0.0181(6) 0.0217(6) 0.0233(6) -0.0013(5) 0.0001(5) -0.0015(5) Cl1 0.02962(19) 0.0413(2) 0.03389(19) -0.00495(16) -0.01575(15) 0.00489(16) Cl2 0.01772(16) 0.0513(2) 0.0385(2) 0.00334(17) -0.00389(14) -0.00889(15) O30 0.0217(5) 0.0205(5) 0.0325(5) 0.0069(4) -0.0019(4) -0.0002(4) O31 0.0257(5) 0.0267(5) 0.0275(5) -0.0073(4) -0.0030(4) 0.0073(4) S1 0.02049(15) 0.01540(14) 0.01687(14) -0.00092(11) -0.00196(11) 0.00099(11) C32 0.0272(8) 0.0330(8) 0.0543(10) 0.0121(7) 0.0026(7) 0.0037(6) C33 0.0230(7) 0.0494(10) 0.0328(8) 0.0048(7) -0.0056(6) -0.0013(7) C34 0.0246(7) 0.0338(8) 0.0424(9) -0.0069(7) -0.0018(6) -0.0038(6) #----------------------------------------------------------------------------# # 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 C2 C3 1.3478(17) . ? C2 C16 1.5034(17) . ? C2 S1 1.7823(13) . ? C3 C4 1.4636(17) . ? C3 H3 0.95 . ? C4 C15 1.3905(17) . ? C4 C5 1.4398(17) . ? C5 C8 1.3859(17) . ? C5 C6 1.4668(17) . ? C6 C7 1.3438(17) . ? C6 H6 0.95 . ? C7 C23 1.5086(17) . ? C7 S1 1.7743(13) . ? C8 C9 1.4102(18) . ? C8 H8 0.95 . ? C9 C14 1.4204(18) . ? C9 C10 1.4211(18) . ? C10 C11 1.372(2) . ? C10 H10 0.95 . ? C11 C12 1.413(2) . ? C11 H11 0.95 . ? C12 C13 1.368(2) . ? C12 H12 0.95 . ? C13 C14 1.4222(18) . ? C13 H13 0.95 . ? C14 C15 1.4127(17) . ? C15 H15 0.95 . ? C16 O31 1.2247(16) . ? C16 C17 1.4961(17) . ? C17 C22 1.3971(18) . ? C17 C18 1.3993(18) . ? C18 C19 1.3889(19) . ? C18 H18 0.95 . ? C19 C20 1.382(2) . ? C19 H19 0.95 . ? C20 C21 1.3876(19) . ? C20 Cl1 1.7450(13) . ? C21 C22 1.3909(18) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? C23 O30 1.2233(16) . ? C23 C24 1.4941(17) . ? C24 C29 1.3941(18) . ? C24 C25 1.4001(18) . ? C25 C26 1.3859(19) . ? C25 H25 0.95 . ? C26 C27 1.388(2) . ? C26 H26 0.95 . ? C27 C28 1.383(2) . ? C27 Cl2 1.7432(14) . ? C28 C29 1.3927(18) . ? C28 H28 0.95 . ? C29 H29 0.95 . ? C32 C33 1.386(3) . ? C32 C32 1.386(4) 2 ? C32 H32 0.95 . ? C33 C34 1.382(2) . ? C33 H33 0.95 . ? C34 C34 1.384(3) 2 ? C34 H34 0.95 . ? 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 C3 C2 C16 118.26(11) . . ? C3 C2 S1 122.16(10) . . ? C16 C2 S1 119.54(9) . . ? C2 C3 C4 128.69(12) . . ? C2 C3 H3 115.7 . . ? C4 C3 H3 115.7 . . ? C15 C4 C5 118.74(11) . . ? C15 C4 C3 116.78(11) . . ? C5 C4 C3 124.28(11) . . ? C8 C5 C4 118.67(11) . . ? C8 C5 C6 116.11(11) . . ? C4 C5 C6 125.03(11) . . ? C7 C6 C5 128.81(12) . . ? C7 C6 H6 115.6 . . ? C5 C6 H6 115.6 . . ? C6 C7 C23 118.35(11) . . ? C6 C7 S1 121.46(10) . . ? C23 C7 S1 119.75(9) . . ? C5 C8 C9 122.69(12) . . ? C5 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C8 C9 C14 118.55(12) . . ? C8 C9 C10 122.18(12) . . ? C14 C9 C10 119.24(12) . . ? C11 C10 C9 120.44(14) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 120.22(13) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.69(13) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.51(13) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C9 118.72(12) . . ? C15 C14 C13 122.38(12) . . ? C9 C14 C13 118.89(12) . . ? C4 C15 C14 122.33(12) . . ? C4 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? O31 C16 C17 119.89(11) . . ? O31 C16 C2 119.34(11) . . ? C17 C16 C2 120.76(11) . . ? C22 C17 C18 119.33(12) . . ? C22 C17 C16 123.13(11) . . ? C18 C17 C16 117.45(12) . . ? C19 C18 C17 120.54(13) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 118.77(12) . . ? C20 C19 H19 120.6 . . ? C18 C19 H19 120.6 . . ? C19 C20 C21 122.23(12) . . ? C19 C20 Cl1 118.47(10) . . ? C21 C20 Cl1 119.30(11) . . ? C20 C21 C22 118.53(13) . . ? C20 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? C21 C22 C17 120.59(12) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? O30 C23 C24 119.03(11) . . ? O30 C23 C7 119.14(11) . . ? C24 C23 C7 121.82(11) . . ? C29 C24 C25 119.45(12) . . ? C29 C24 C23 122.81(11) . . ? C25 C24 C23 117.42(11) . . ? C26 C25 C24 120.42(13) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C27 118.93(13) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C28 C27 C26 121.81(12) . . ? C28 C27 Cl2 119.02(11) . . ? C26 C27 Cl2 119.15(11) . . ? C27 C28 C29 118.89(13) . . ? C27 C28 H28 120.6 . . ? C29 C28 H28 120.6 . . ? C28 C29 C24 120.41(12) . . ? C28 C29 H29 119.8 . . ? C24 C29 H29 119.8 . . ? C7 S1 C2 100.28(6) . . ? C33 C32 C32 119.97(10) . 2 ? C33 C32 H32 120 . . ? C32 C32 H32 120 2 . ? C34 C33 C32 119.92(15) . . ? C34 C33 H33 120 . . ? C32 C33 H33 120 . . ? C33 C34 C34 120.11(10) . 2 ? C33 C34 H34 119.9 . . ? C34 C34 H34 119.9 2 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C2 C3 C4 176.32(12) . . . . ? S1 C2 C3 C4 -1.52(19) . . . . ? C2 C3 C4 C15 146.16(13) . . . . ? C2 C3 C4 C5 -39.0(2) . . . . ? C15 C4 C5 C8 -1.32(18) . . . . ? C3 C4 C5 C8 -176.07(12) . . . . ? C15 C4 C5 C6 173.38(12) . . . . ? C3 C4 C5 C6 -1.4(2) . . . . ? C8 C5 C6 C7 -145.37(14) . . . . ? C4 C5 C6 C7 39.8(2) . . . . ? C5 C6 C7 C23 176.07(12) . . . . ? C5 C6 C7 S1 3.72(19) . . . . ? C4 C5 C8 C9 -3.72(19) . . . . ? C6 C5 C8 C9 -178.88(12) . . . . ? C5 C8 C9 C14 5.3(2) . . . . ? C5 C8 C9 C10 -176.65(13) . . . . ? C8 C9 C10 C11 -176.83(14) . . . . ? C14 C9 C10 C11 1.2(2) . . . . ? C9 C10 C11 C12 -0.5(2) . . . . ? C10 C11 C12 C13 -0.3(2) . . . . ? C11 C12 C13 C14 0.5(2) . . . . ? C8 C9 C14 C15 -1.90(19) . . . . ? C10 C9 C14 C15 -179.98(12) . . . . ? C8 C9 C14 C13 177.05(12) . . . . ? C10 C9 C14 C13 -1.02(19) . . . . ? C12 C13 C14 C15 179.13(13) . . . . ? C12 C13 C14 C9 0.2(2) . . . . ? C5 C4 C15 C14 4.71(19) . . . . ? C3 C4 C15 C14 179.85(12) . . . . ? C9 C14 C15 C4 -3.08(19) . . . . ? C13 C14 C15 C4 178.01(12) . . . . ? C3 C2 C16 O31 -25.60(18) . . . . ? S1 C2 C16 O31 152.30(11) . . . . ? C3 C2 C16 C17 155.24(12) . . . . ? S1 C2 C16 C17 -26.87(16) . . . . ? O31 C16 C17 C22 154.12(13) . . . . ? C2 C16 C17 C22 -26.72(18) . . . . ? O31 C16 C17 C18 -22.53(18) . . . . ? C2 C16 C17 C18 156.63(12) . . . . ? C22 C17 C18 C19 0.6(2) . . . . ? C16 C17 C18 C19 177.43(12) . . . . ? C17 C18 C19 C20 -0.6(2) . . . . ? C18 C19 C20 C21 0.0(2) . . . . ? C18 C19 C20 Cl1 -179.08(11) . . . . ? C19 C20 C21 C22 0.7(2) . . . . ? Cl1 C20 C21 C22 179.72(10) . . . . ? C20 C21 C22 C17 -0.67(19) . . . . ? C18 C17 C22 C21 0.02(19) . . . . ? C16 C17 C22 C21 -176.58(12) . . . . ? C6 C7 C23 O30 -21.13(18) . . . . ? S1 C7 C23 O30 151.36(10) . . . . ? C6 C7 C23 C24 158.45(12) . . . . ? S1 C7 C23 C24 -29.07(16) . . . . ? O30 C23 C24 C29 143.61(13) . . . . ? C7 C23 C24 C29 -35.97(18) . . . . ? O30 C23 C24 C25 -29.89(18) . . . . ? C7 C23 C24 C25 150.53(12) . . . . ? C29 C24 C25 C26 -0.9(2) . . . . ? C23 C24 C25 C26 172.79(12) . . . . ? C24 C25 C26 C27 -1.7(2) . . . . ? C25 C26 C27 C28 3.2(2) . . . . ? C25 C26 C27 Cl2 -175.52(11) . . . . ? C26 C27 C28 C29 -1.9(2) . . . . ? Cl2 C27 C28 C29 176.83(11) . . . . ? C27 C28 C29 C24 -0.9(2) . . . . ? C25 C24 C29 C28 2.3(2) . . . . ? C23 C24 C29 C28 -171.11(12) . . . . ? C6 C7 S1 C2 -61.47(12) . . . . ? C23 C7 S1 C2 126.28(10) . . . . ? C3 C2 S1 C7 60.32(12) . . . . ? C16 C2 S1 C7 -117.49(10) . . . . ? C32 C32 C33 C34 -0.3(3) 2 . . . ? C32 C33 C34 C34 0.3(3) . . . 2 ? data_unsolvated _database_code_depnum_ccdc_archive 'CCDC 239493' _audit_creation_date 2004-03-08T16:27:37-00:00 _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 'C28 H16 Cl2 O2 S' _chemical_formula_sum 'C28 H16 Cl2 O2 S' _chemical_formula_weight 487.37 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 13.9910(13) _cell_length_b 10.2442(8) _cell_length_c 15.5461(13) _cell_angle_alpha 90 _cell_angle_beta 99.564(3) _cell_angle_gamma 90 _cell_volume 2197.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5303 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 30.034 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.072 0 0 1 0.038 -1 0 0 0.116 1 0 0 0.178 1 -1 0 0.116 -1 1 0 0.154 -1 6 0 0.183 1 1 0 0.231 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.416 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; P. Coppens, L. Leiserowitz, D Rabinovich, Acta Cryst. (1965), 18, 1035-1038 ; _exptl_absorpt_correction_T_min 0.873 _exptl_absorpt_correction_T_max 0.955 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(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 0.588179E-1 _diffrn_orient_matrix_ub_12 -0.246627E-1 _diffrn_orient_matrix_ub_13 0.426907E-1 _diffrn_orient_matrix_ub_21 -0.422453E-1 _diffrn_orient_matrix_ub_22 -0.27774E-1 _diffrn_orient_matrix_ub_23 0.426435E-1 _diffrn_orient_matrix_ub_31 -0.30717E-2 _diffrn_orient_matrix_ub_32 -0.902734E-1 _diffrn_orient_matrix_ub_33 -0.24783E-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 0.041 _diffrn_reflns_av_unetI/netI 0.0363 _diffrn_reflns_number 5040 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 5040 _reflns_number_gt 4060 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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^)+(0.0541P)^2^+0.8037P] 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 5040 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.284 _refine_diff_density_min -0.28 _refine_diff_density_rms 0.074 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 C2 C 0.19021(12) 0.39040(16) 0.05054(12) 0.0197(4) Uani 1 1 d . . . C3 C 0.13097(12) 0.33256(16) -0.01543(12) 0.0200(4) Uani 1 1 d . . . H3 H 0.1098 0.2475 -0.0032 0.024 Uiso 1 1 calc R . . C4 C 0.09448(12) 0.38100(17) -0.10286(11) 0.0194(4) Uani 1 1 d . . . C5 C 0.06722(12) 0.51431(17) -0.12323(12) 0.0201(4) Uani 1 1 d . . . C6 C 0.07180(13) 0.62017(16) -0.05939(12) 0.0207(4) Uani 1 1 d . . . H6 H 0.0204 0.6817 -0.0703 0.025 Uiso 1 1 calc R . . C7 C 0.13730(12) 0.64346(16) 0.01195(12) 0.0202(4) Uani 1 1 d . . . C8 C 0.02532(13) 0.54490(17) -0.20729(12) 0.0236(4) Uani 1 1 d . . . H8 H 0.004 0.6319 -0.2197 0.028 Uiso 1 1 calc R . . C9 C 0.01265(13) 0.45324(17) -0.27565(12) 0.0226(4) Uani 1 1 d . . . C10 C -0.02902(14) 0.48543(19) -0.36239(13) 0.0290(4) Uani 1 1 d . . . H10 H -0.0465 0.5733 -0.3768 0.035 Uiso 1 1 calc R . . C11 C -0.04438(15) 0.3912(2) -0.42563(13) 0.0318(4) Uani 1 1 d . . . H11 H -0.0731 0.4138 -0.4834 0.038 Uiso 1 1 calc R . . C12 C -0.01755(14) 0.2604(2) -0.40509(13) 0.0304(4) Uani 1 1 d . . . H12 H -0.028 0.1957 -0.4494 0.036 Uiso 1 1 calc R . . C13 C 0.02308(13) 0.22629(18) -0.32250(13) 0.0259(4) Uani 1 1 d . . . H13 H 0.0409 0.138 -0.3098 0.031 Uiso 1 1 calc R . . C14 C 0.03912(12) 0.32124(17) -0.25526(12) 0.0219(4) Uani 1 1 d . . . C15 C 0.07715(12) 0.28865(17) -0.16851(12) 0.0213(4) Uani 1 1 d . . . H15 H 0.0915 0.1998 -0.1544 0.026 Uiso 1 1 calc R . . C16 C 0.20952(13) 0.32127(17) 0.13674(12) 0.0223(4) Uani 1 1 d . . . C17 C 0.29940(13) 0.34680(17) 0.20085(12) 0.0226(4) Uani 1 1 d . . . C18 C 0.29621(14) 0.3245(2) 0.28883(13) 0.0296(4) Uani 1 1 d . . . H18 H 0.2368 0.2998 0.3062 0.036 Uiso 1 1 calc R . . C19 C 0.37857(15) 0.3378(2) 0.35113(13) 0.0329(5) Uani 1 1 d . . . H19 H 0.376 0.3245 0.4112 0.039 Uiso 1 1 calc R . . C20 C 0.46489(14) 0.37103(18) 0.32401(13) 0.0263(4) Uani 1 1 d . . . C21 C 0.47026(14) 0.39357(17) 0.23749(13) 0.0247(4) Uani 1 1 d . . . H21 H 0.5302 0.4164 0.2204 0.03 Uiso 1 1 calc R . . C22 C 0.38651(13) 0.38235(16) 0.17557(12) 0.0219(4) Uani 1 1 d . . . H22 H 0.3889 0.399 0.1159 0.026 Uiso 1 1 calc R . . C23 C 0.12510(12) 0.76571(17) 0.06360(12) 0.0216(4) Uani 1 1 d . . . C24 C 0.17087(12) 0.78168(17) 0.15657(12) 0.0219(4) Uani 1 1 d . . . C25 C 0.18962(13) 0.90944(18) 0.18687(13) 0.0255(4) Uani 1 1 d . . . H25 H 0.1781 0.9804 0.1472 0.031 Uiso 1 1 calc R . . C26 C 0.22465(14) 0.9333(2) 0.27376(14) 0.0302(4) Uani 1 1 d . . . H26 H 0.2384 1.0199 0.294 0.036 Uiso 1 1 calc R . . C27 C 0.23936(14) 0.8288(2) 0.33103(13) 0.0305(4) Uani 1 1 d . . . C28 C 0.22232(14) 0.7016(2) 0.30301(13) 0.0294(4) Uani 1 1 d . . . H28 H 0.2336 0.6311 0.3432 0.035 Uiso 1 1 calc R . . C29 C 0.18864(13) 0.67842(18) 0.21569(13) 0.0243(4) Uani 1 1 d . . . H29 H 0.1774 0.5913 0.1956 0.029 Uiso 1 1 calc R . . Cl1 Cl 0.56988(4) 0.38392(6) 0.40128(3) 0.03979(15) Uani 1 1 d . . . Cl2 Cl 0.27805(4) 0.85870(7) 0.44164(4) 0.04581(17) Uani 1 1 d . . . O30 O 0.07508(10) 0.85417(12) 0.02735(9) 0.0278(3) Uani 1 1 d . . . O31 O 0.15002(10) 0.24235(13) 0.15454(9) 0.0297(3) Uani 1 1 d . . . S1 S 0.24317(3) 0.54632(4) 0.03864(3) 0.02120(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0197(8) 0.0159(8) 0.0233(9) 0.0019(7) 0.0032(7) 0.0014(6) C3 0.0202(8) 0.0163(8) 0.0237(9) 0.0013(7) 0.0041(7) 0.0012(6) C4 0.0181(8) 0.0211(8) 0.0188(9) 0.0000(7) 0.0023(7) -0.0003(6) C5 0.0194(8) 0.0193(8) 0.0219(9) 0.0003(7) 0.0040(7) -0.0014(6) C6 0.0221(8) 0.0177(8) 0.0227(9) 0.0018(7) 0.0049(7) 0.0014(7) C7 0.0212(8) 0.0171(8) 0.0232(9) 0.0014(7) 0.0061(7) -0.0006(6) C8 0.0266(9) 0.0171(8) 0.0264(10) 0.0011(7) 0.0025(7) -0.0003(7) C9 0.0234(8) 0.0229(9) 0.0212(9) 0.0023(7) 0.0029(7) -0.0046(7) C10 0.0365(10) 0.0265(9) 0.0225(10) 0.0038(8) 0.0008(8) -0.0031(8) C11 0.0387(11) 0.0358(11) 0.0197(10) 0.0032(8) 0.0011(8) -0.0063(9) C12 0.0349(10) 0.0333(10) 0.0228(10) -0.0073(8) 0.0046(8) -0.0055(8) C13 0.0287(9) 0.0237(9) 0.0251(10) -0.0030(8) 0.0035(8) -0.0006(7) C14 0.0202(8) 0.0229(9) 0.0228(9) -0.0007(7) 0.0045(7) -0.0021(7) C15 0.0202(8) 0.0193(8) 0.0241(9) 0.0003(7) 0.0031(7) 0.0004(7) C16 0.0245(9) 0.0177(8) 0.0239(10) -0.0007(7) 0.0022(7) 0.0023(7) C17 0.0265(9) 0.0192(8) 0.0206(9) 0.0007(7) -0.0002(7) 0.0028(7) C18 0.0269(9) 0.0363(11) 0.0252(10) 0.0049(8) 0.0032(8) -0.0022(8) C19 0.0365(11) 0.0408(11) 0.0200(10) 0.0061(9) 0.0009(8) -0.0051(9) C20 0.0277(9) 0.0244(9) 0.0236(10) 0.0010(7) -0.0047(8) -0.0007(7) C21 0.0265(9) 0.0199(9) 0.0275(10) -0.0005(7) 0.0034(7) 0.0013(7) C22 0.0269(9) 0.0187(8) 0.0199(9) -0.0001(7) 0.0032(7) 0.0027(7) C23 0.0226(8) 0.0194(8) 0.0238(10) -0.0010(7) 0.0066(7) -0.0020(7) C24 0.0211(8) 0.0227(9) 0.0226(10) -0.0017(7) 0.0061(7) -0.0002(7) C25 0.0257(9) 0.0237(9) 0.0285(10) -0.0029(8) 0.0085(8) 0.0013(7) C26 0.0281(10) 0.0301(10) 0.0325(11) -0.0127(8) 0.0058(8) -0.0015(8) C27 0.0238(9) 0.0435(12) 0.0243(10) -0.0090(9) 0.0047(8) -0.0002(8) C28 0.0273(9) 0.0363(11) 0.0246(10) 0.0026(8) 0.0040(8) 0.0024(8) C29 0.0250(9) 0.0241(9) 0.0246(10) -0.0004(7) 0.0059(7) 0.0006(7) Cl1 0.0339(3) 0.0517(3) 0.0291(3) 0.0069(2) -0.0085(2) -0.0074(2) Cl2 0.0395(3) 0.0692(4) 0.0263(3) -0.0142(3) -0.0017(2) 0.0028(3) O30 0.0358(7) 0.0211(6) 0.0253(7) 0.0002(5) 0.0019(6) 0.0067(6) O31 0.0311(7) 0.0285(7) 0.0282(8) 0.0069(6) 0.0009(6) -0.0060(6) S1 0.0202(2) 0.0175(2) 0.0253(2) 0.00055(17) 0.00203(17) -0.00056(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 C2 C3 1.344(2) . ? C2 C16 1.500(3) . ? C2 S1 1.7833(17) . ? C3 C4 1.457(2) . ? C3 H3 0.95 . ? C4 C15 1.383(2) . ? C4 C5 1.439(2) . ? C5 C8 1.377(3) . ? C5 C6 1.464(2) . ? C6 C7 1.338(3) . ? C6 H6 0.95 . ? C7 C23 1.513(2) . ? C7 S1 1.7755(17) . ? C8 C9 1.407(3) . ? C8 H8 0.95 . ? C9 C10 1.416(3) . ? C9 C14 1.424(2) . ? C10 C11 1.369(3) . ? C10 H10 0.95 . ? C11 C12 1.414(3) . ? C11 H11 0.95 . ? C12 C13 1.361(3) . ? C12 H12 0.95 . ? C13 C14 1.418(3) . ? C13 H13 0.95 . ? C14 C15 1.405(3) . ? C15 H15 0.95 . ? C16 O31 1.225(2) . ? C16 C17 1.492(2) . ? C17 C22 1.390(3) . ? C17 C18 1.395(3) . ? C18 C19 1.383(3) . ? C18 H18 0.95 . ? C19 C20 1.386(3) . ? C19 H19 0.95 . ? C20 C21 1.379(3) . ? C20 Cl1 1.7413(19) . ? C21 C22 1.392(3) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? C23 O30 1.224(2) . ? C23 C24 1.489(3) . ? C24 C29 1.396(3) . ? C24 C25 1.401(3) . ? C25 C26 1.380(3) . ? C25 H25 0.95 . ? C26 C27 1.386(3) . ? C26 H26 0.95 . ? C27 C28 1.382(3) . ? C27 Cl2 1.742(2) . ? C28 C29 1.382(3) . ? C28 H28 0.95 . ? C29 H29 0.95 . ? 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 C3 C2 C16 118.05(15) . . ? C3 C2 S1 121.99(14) . . ? C16 C2 S1 119.95(13) . . ? C2 C3 C4 129.61(16) . . ? C2 C3 H3 115.2 . . ? C4 C3 H3 115.2 . . ? C15 C4 C5 118.64(16) . . ? C15 C4 C3 116.52(15) . . ? C5 C4 C3 124.57(16) . . ? C8 C5 C4 118.71(16) . . ? C8 C5 C6 116.02(16) . . ? C4 C5 C6 125.00(16) . . ? C7 C6 C5 129.86(16) . . ? C7 C6 H6 115.1 . . ? C5 C6 H6 115.1 . . ? C6 C7 C23 117.75(15) . . ? C6 C7 S1 121.59(14) . . ? C23 C7 S1 120.23(13) . . ? C5 C8 C9 123.05(16) . . ? C5 C8 H8 118.5 . . ? C9 C8 H8 118.5 . . ? C8 C9 C10 122.96(17) . . ? C8 C9 C14 118.05(17) . . ? C10 C9 C14 118.93(17) . . ? C11 C10 C9 120.69(18) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.13(19) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.68(18) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.63(18) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 122.19(17) . . ? C15 C14 C9 118.83(16) . . ? C13 C14 C9 118.94(17) . . ? C4 C15 C14 122.52(16) . . ? C4 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? O31 C16 C17 119.59(17) . . ? O31 C16 C2 119.03(16) . . ? C17 C16 C2 121.38(16) . . ? C22 C17 C18 119.52(17) . . ? C22 C17 C16 122.57(17) . . ? C18 C17 C16 117.74(17) . . ? C19 C18 C17 120.78(18) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 118.54(19) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C21 C20 C19 121.95(17) . . ? C21 C20 Cl1 118.94(15) . . ? C19 C20 Cl1 119.11(15) . . ? C20 C21 C22 118.99(18) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C17 C22 C21 120.20(18) . . ? C17 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? O30 C23 C24 119.10(16) . . ? O30 C23 C7 118.36(16) . . ? C24 C23 C7 122.53(15) . . ? C29 C24 C25 118.92(17) . . ? C29 C24 C23 123.81(16) . . ? C25 C24 C23 117.08(16) . . ? C26 C25 C24 120.73(18) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C25 C26 C27 118.83(18) . . ? C25 C26 H26 120.6 . . ? C27 C26 H26 120.6 . . ? C28 C27 C26 121.79(19) . . ? C28 C27 Cl2 119.08(17) . . ? C26 C27 Cl2 119.12(16) . . ? C29 C28 C27 118.97(19) . . ? C29 C28 H28 120.5 . . ? C27 C28 H28 120.5 . . ? C28 C29 C24 120.74(18) . . ? C28 C29 H29 119.6 . . ? C24 C29 H29 119.6 . . ? C7 S1 C2 100.45(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C2 C3 C4 175.05(17) . . . . ? S1 C2 C3 C4 -3.5(3) . . . . ? C2 C3 C4 C15 148.84(18) . . . . ? C2 C3 C4 C5 -37.3(3) . . . . ? C15 C4 C5 C8 -0.3(2) . . . . ? C3 C4 C5 C8 -174.02(16) . . . . ? C15 C4 C5 C6 173.54(16) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C8 C5 C6 C7 -148.86(19) . . . . ? C4 C5 C6 C7 37.2(3) . . . . ? C5 C6 C7 C23 177.21(17) . . . . ? C5 C6 C7 S1 4.7(3) . . . . ? C4 C5 C8 C9 -3.6(3) . . . . ? C6 C5 C8 C9 -177.97(16) . . . . ? C5 C8 C9 C10 -178.93(17) . . . . ? C5 C8 C9 C14 4.0(3) . . . . ? C8 C9 C10 C11 -176.58(18) . . . . ? C14 C9 C10 C11 0.5(3) . . . . ? C9 C10 C11 C12 -0.8(3) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C15 177.29(17) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? C8 C9 C14 C15 -0.5(2) . . . . ? C10 C9 C14 C15 -177.68(16) . . . . ? C8 C9 C14 C13 177.34(16) . . . . ? C10 C9 C14 C13 0.1(3) . . . . ? C5 C4 C15 C14 3.7(3) . . . . ? C3 C4 C15 C14 177.99(16) . . . . ? C13 C14 C15 C4 178.91(17) . . . . ? C9 C14 C15 C4 -3.4(3) . . . . ? C3 C2 C16 O31 -24.4(3) . . . . ? S1 C2 C16 O31 154.23(14) . . . . ? C3 C2 C16 C17 155.61(17) . . . . ? S1 C2 C16 C17 -25.8(2) . . . . ? O31 C16 C17 C22 149.59(18) . . . . ? C2 C16 C17 C22 -30.4(2) . . . . ? O31 C16 C17 C18 -25.7(3) . . . . ? C2 C16 C17 C18 154.28(17) . . . . ? C22 C17 C18 C19 0.3(3) . . . . ? C16 C17 C18 C19 175.71(18) . . . . ? C17 C18 C19 C20 -1.4(3) . . . . ? C18 C19 C20 C21 1.4(3) . . . . ? C18 C19 C20 Cl1 -178.29(16) . . . . ? C19 C20 C21 C22 -0.1(3) . . . . ? Cl1 C20 C21 C22 179.53(13) . . . . ? C18 C17 C22 C21 1.0(3) . . . . ? C16 C17 C22 C21 -174.21(16) . . . . ? C20 C21 C22 C17 -1.1(3) . . . . ? C6 C7 C23 O30 -20.1(2) . . . . ? S1 C7 C23 O30 152.53(14) . . . . ? C6 C7 C23 C24 159.47(17) . . . . ? S1 C7 C23 C24 -27.9(2) . . . . ? O30 C23 C24 C29 148.53(18) . . . . ? C7 C23 C24 C29 -31.0(3) . . . . ? O30 C23 C24 C25 -26.3(2) . . . . ? C7 C23 C24 C25 154.21(16) . . . . ? C29 C24 C25 C26 -0.3(3) . . . . ? C23 C24 C25 C26 174.77(16) . . . . ? C24 C25 C26 C27 -1.2(3) . . . . ? C25 C26 C27 C28 1.7(3) . . . . ? C25 C26 C27 Cl2 -176.96(14) . . . . ? C26 C27 C28 C29 -0.8(3) . . . . ? Cl2 C27 C28 C29 177.92(14) . . . . ? C27 C28 C29 C24 -0.8(3) . . . . ? C25 C24 C29 C28 1.3(3) . . . . ? C23 C24 C29 C28 -173.43(17) . . . . ? C6 C7 S1 C2 -60.85(16) . . . . ? C23 C7 S1 C2 126.86(14) . . . . ? C3 C2 S1 C7 60.40(16) . . . . ? C16 C2 S1 C7 -118.17(14) . . . . ?