# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jay Siegel' 'Kim K Baldridge' 'Kenneth I Hardcastle' 'T. Jon Seiders' _publ_contact_author_name 'Jay Siegel' _publ_contact_author_email JSS@OCI.UZH.CH _publ_section_title ; Synthesis Structure and Properties of Decaphenylthiocorannulene ; # Attachment 'Cmpnd_5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 748565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C80 H50 S10' _chemical_formula_sum 'C80 H50 S10' _chemical_formula_weight 1331.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.227(3) _cell_length_b 15.372(3) _cell_length_c 16.161(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.447(3) _cell_angle_gamma 90.00 _cell_volume 3779.3(11) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4792 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 28.50 _exptl_crystal_description plate _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1380 _exptl_absorpt_coefficient_mu 0.332 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 39908 _diffrn_reflns_av_R_equivalents 0.1263 _diffrn_reflns_av_sigmaI/netI 0.1738 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8616 _reflns_number_gt 3014 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.218 0.437 0.290 158.6 47.2 2 -0.218 0.563 0.710 158.8 48.0 3 0.282 0.936 0.209 157.7 46.7 4 0.718 0.063 0.791 157.5 47.9 _platon_squeeze_details ; A.L. Spek (1990) Acta Cryst. A46, C34 "PLATON-A Multipurpose Crystallographic Tool," Utrecht University, Utrecht, The Netherlands, A.L. Spek (2006) ; _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^)+(0.0570P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8616 _refine_ls_number_parameters 381 _refine_ls_number_restraints 77 _refine_ls_R_factor_all 0.2242 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.1743 _refine_ls_wR_factor_gt 0.1485 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6281(5) 1.1437(3) 0.0976(5) 0.035(2) Uiso 0.50 1 d PD A -1 C2 C 0.6336(4) 1.0520(3) 0.0885(4) 0.030(2) Uiso 0.50 1 d PD A -1 C3 C 0.6692(5) 0.9779(4) 0.1355(5) 0.031(2) Uiso 0.50 1 d PD A -1 C4 C 0.6512(5) 0.8927(4) 0.1128(5) 0.033(2) Uiso 0.50 1 d PD A -1 C5 C 0.5901(4) 0.8652(4) 0.0461(4) 0.029(2) Uiso 0.50 1 d PD A -1 C6 C 0.5452(5) 0.7875(5) 0.0194(5) 0.034(2) Uiso 0.50 1 d PD A -1 C7 C 0.4827(5) 0.7893(5) -0.0453(5) 0.038(2) Uiso 0.50 1 d PD A -1 C8 C 0.4464(4) 0.8660(4) -0.0840(5) 0.037(2) Uiso 0.50 1 d PD A -1 C9 C 0.3696(5) 0.8920(5) -0.1331(5) 0.037(2) Uiso 0.50 1 d PD . -1 C10 C 0.3504(5) 0.9767(4) -0.1566(5) 0.032(2) Uiso 0.50 1 d PD . -1 C11 C 0.3981(4) 1.0513(5) -0.1215(5) 0.037(2) Uiso 0.50 1 d PD A -1 C12 C 0.3864(5) 1.1436(5) -0.1150(5) 0.031(2) Uiso 0.50 1 d PD . -1 C13 C 0.4427(5) 1.1967(5) -0.0683(5) 0.034(2) Uiso 0.50 1 d PD . -1 C14 C 0.5141(5) 1.1651(4) -0.0157(5) 0.035(2) Uiso 0.50 1 d PD A -1 C15 C 0.5681(5) 1.1965(5) 0.0548(5) 0.036(2) Uiso 0.50 1 d PD . -1 C16 C 0.5308(4) 1.0785(3) -0.0301(4) 0.034(2) Uiso 0.50 1 d PD A -1 C17 C 0.5867(4) 1.0240(3) 0.0189(4) 0.033(2) Uiso 0.50 1 d PD A -1 C18 C 0.5666(4) 0.9364(3) -0.0015(4) 0.037(2) Uiso 0.50 1 d PD A -1 C19 C 0.4960(4) 0.9377(3) -0.0616(4) 0.034(2) Uiso 0.50 1 d PD A -1 C20 C 0.4750(4) 1.0253(3) -0.0809(4) 0.034(2) Uiso 0.50 1 d PD A -1 C21 C 0.6664(3) 0.9587(3) 0.3064(3) 0.0527(13) Uani 1 1 d D A . C22 C 0.5808(3) 0.9871(4) 0.3143(4) 0.093(2) Uani 1 1 d D . . H22 H 0.5570 1.0272 0.2766 0.111 Uiso 1 1 calc R . . C23 C 0.5301(4) 0.9568(5) 0.3774(4) 0.134(3) Uani 1 1 d D . . H23 H 0.4717 0.9740 0.3795 0.161 Uiso 1 1 calc R . . C24 C 0.5655(4) 0.9010(5) 0.4375(5) 0.119(3) Uani 1 1 d D . . H24 H 0.5320 0.8815 0.4806 0.143 Uiso 1 1 calc R . . C25 C 0.6521(4) 0.8751(4) 0.4316(3) 0.097(2) Uani 1 1 d D . . H25 H 0.6773 0.8382 0.4716 0.116 Uiso 1 1 calc R . . C26 C 0.7019(4) 0.9035(3) 0.3668(3) 0.0731(16) Uani 1 1 d D . . H26 H 0.7599 0.8851 0.3638 0.088 Uiso 1 1 calc R . . C31 C 0.7594(3) 0.7587(3) 0.0769(3) 0.0537(13) Uani 1 1 d . A . C32 C 0.7763(4) 0.8020(4) 0.0055(4) 0.0852(18) Uani 1 1 d . . . H32 H 0.7631 0.8609 0.0009 0.102 Uiso 1 1 calc R . . C33 C 0.8131(5) 0.7588(6) -0.0603(5) 0.132(3) Uani 1 1 d . . . H33 H 0.8219 0.7870 -0.1102 0.159 Uiso 1 1 calc R . . C34 C 0.8361(5) 0.6724(6) -0.0491(5) 0.128(3) Uani 1 1 d . . . H34 H 0.8598 0.6414 -0.0922 0.153 Uiso 1 1 calc R . . C35 C 0.8242(4) 0.6331(5) 0.0246(5) 0.112(2) Uani 1 1 d . . . H35 H 0.8427 0.5759 0.0324 0.135 Uiso 1 1 calc R . . C36 C 0.7858(4) 0.6753(4) 0.0870(4) 0.0776(18) Uani 1 1 d . . . H36 H 0.7776 0.6469 0.1369 0.093 Uiso 1 1 calc R . . C41 C 0.4664(4) 0.6458(3) 0.0923(3) 0.0600(14) Uani 1 1 d . A . C42 C 0.3949(5) 0.6916(4) 0.1129(4) 0.097(2) Uani 1 1 d . . . H42 H 0.3983 0.7518 0.1175 0.116 Uiso 1 1 calc R . . C43 C 0.3168(5) 0.6499(6) 0.1271(5) 0.126(3) Uani 1 1 d . . . H43 H 0.2672 0.6809 0.1411 0.151 Uiso 1 1 calc R . . C44 C 0.3147(5) 0.5595(6) 0.1196(5) 0.128(3) Uani 1 1 d . . . H44 H 0.2622 0.5299 0.1262 0.153 Uiso 1 1 calc R . . C45 C 0.3865(6) 0.5156(5) 0.1033(5) 0.133(3) Uani 1 1 d . . . H45 H 0.3848 0.4551 0.1020 0.160 Uiso 1 1 calc R . . C46 C 0.4620(4) 0.5568(4) 0.0887(4) 0.087(2) Uani 1 1 d . . . H46 H 0.5115 0.5249 0.0762 0.104 Uiso 1 1 calc R . . C51 C 0.4797(3) 0.7109(4) -0.1968(3) 0.0602(14) Uani 1 1 d . A . C52 C 0.5384(5) 0.7724(5) -0.2176(5) 0.111(3) Uani 1 1 d . . . H52 H 0.5668 0.8059 -0.1767 0.134 Uiso 1 1 calc R . . C53 C 0.5556(7) 0.7850(6) -0.2983(8) 0.180(5) Uani 1 1 d . . . H53 H 0.5925 0.8302 -0.3129 0.216 Uiso 1 1 calc R . . C54 C 0.5200(9) 0.7329(8) -0.3572(7) 0.158(5) Uani 1 1 d . . . H54 H 0.5328 0.7415 -0.4124 0.190 Uiso 1 1 calc R . . C55 C 0.4664(6) 0.6689(7) -0.3368(6) 0.130(3) Uani 1 1 d . . . H55 H 0.4440 0.6314 -0.3776 0.156 Uiso 1 1 calc R . . C56 C 0.4438(3) 0.6573(4) -0.2563(4) 0.086(2) Uani 1 1 d . . . H56 H 0.4047 0.6137 -0.2425 0.103 Uiso 1 1 calc R . . C61 C 0.8068(3) 1.1534(3) 0.1315(3) 0.0491(13) Uani 1 1 d . A . C62 C 0.8166(4) 1.1247(4) 0.0511(4) 0.0810(18) Uani 1 1 d . . . H62 H 0.7691 1.1244 0.0130 0.097 Uiso 1 1 calc R . . C63 C 0.8973(5) 1.0971(5) 0.0293(4) 0.110(2) Uani 1 1 d . . . H63 H 0.9039 1.0755 -0.0239 0.131 Uiso 1 1 calc R . . C64 C 0.9694(4) 1.1002(5) 0.0835(5) 0.106(2) Uani 1 1 d . . . H64 H 1.0241 1.0816 0.0670 0.127 Uiso 1 1 calc R . . C65 C 0.9598(4) 1.1306(4) 0.1618(4) 0.098(2) Uani 1 1 d . . . H65 H 1.0079 1.1333 0.1992 0.117 Uiso 1 1 calc R . . C66 C 0.87824(3) 1.15734(4) 0.18497(3) 0.0703(16) Uani 1 1 d . . . H66 H 0.8717 1.1785 0.2383 0.084 Uiso 1 1 calc R . . S1 S 0.70558(3) 1.19407(4) 0.16492(3) 0.0518(4) Uani 1 1 d RD . . S2 S 0.73170(3) 1.00139(4) 0.23113(3) 0.0490(3) Uani 1 1 d RD . . S3 S 0.71313(3) 0.81168(4) 0.16251(3) 0.0532(4) Uani 1 1 d RD . . S4 S 0.57088(3) 0.69031(4) 0.07592(3) 0.0600(4) Uani 1 1 d RD . . S5 S 0.45211(3) 0.69187(4) -0.09248(3) 0.0579(4) Uani 1 1 d RD . . 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 C21 0.061(3) 0.050(3) 0.046(3) 0.000(3) -0.013(3) 0.005(3) C22 0.069(4) 0.133(6) 0.076(4) 0.040(4) 0.003(3) -0.007(4) C23 0.091(6) 0.164(8) 0.149(8) 0.051(6) 0.017(6) 0.004(5) C24 0.117(7) 0.124(7) 0.118(7) -0.009(6) 0.028(6) -0.022(5) C25 0.176(7) 0.059(4) 0.056(4) 0.014(3) 0.004(5) -0.009(5) C26 0.106(5) 0.051(4) 0.062(4) 0.003(3) -0.003(4) 0.022(3) C31 0.051(3) 0.050(3) 0.059(4) 0.007(3) -0.005(3) 0.003(3) C32 0.092(4) 0.083(4) 0.081(5) 0.019(4) 0.009(4) 0.018(4) C33 0.149(7) 0.157(8) 0.094(6) 0.034(6) 0.049(5) 0.058(6) C34 0.135(6) 0.148(8) 0.103(7) 0.010(6) 0.029(5) 0.074(6) C35 0.130(6) 0.095(6) 0.112(7) 0.003(5) 0.003(5) 0.057(5) C36 0.089(4) 0.070(4) 0.075(4) 0.002(4) 0.008(3) 0.038(3) C41 0.078(4) 0.042(3) 0.058(4) 0.007(3) -0.011(3) -0.003(3) C42 0.100(5) 0.066(4) 0.126(6) 0.018(4) 0.020(4) -0.009(4) C43 0.096(6) 0.111(7) 0.172(8) 0.040(6) 0.029(5) 0.001(5) C44 0.099(6) 0.103(7) 0.181(9) 0.049(6) -0.006(6) -0.055(5) C45 0.112(6) 0.081(6) 0.209(10) 0.020(6) 0.031(6) -0.004(6) C46 0.094(5) 0.055(4) 0.112(6) 0.007(4) 0.014(4) -0.016(4) C51 0.057(3) 0.064(4) 0.059(4) -0.010(3) 0.003(3) 0.011(3) C52 0.135(6) 0.116(6) 0.087(6) -0.015(5) 0.049(5) -0.039(5) C53 0.249(13) 0.119(8) 0.183(12) -0.005(8) 0.131(11) -0.007(8) C54 0.231(14) 0.163(12) 0.085(8) 0.041(7) 0.062(9) 0.086(10) C55 0.121(7) 0.196(11) 0.071(7) -0.047(6) -0.016(5) 0.053(7) C56 0.063(4) 0.118(6) 0.076(5) -0.026(4) -0.007(4) 0.002(4) C61 0.059(3) 0.043(3) 0.045(3) 0.002(3) -0.006(3) -0.007(2) C62 0.065(4) 0.100(5) 0.079(5) -0.003(4) 0.002(4) -0.007(4) C63 0.091(5) 0.152(7) 0.089(5) -0.044(5) 0.039(5) -0.013(5) C64 0.054(4) 0.138(6) 0.127(7) -0.017(6) 0.023(5) 0.001(4) C65 0.057(4) 0.149(6) 0.086(5) -0.022(5) -0.007(4) 0.007(4) C66 0.055(4) 0.088(4) 0.067(4) -0.015(3) -0.007(3) 0.008(3) S1 0.0478(8) 0.0420(8) 0.0638(9) -0.0113(7) -0.0189(7) -0.0035(6) S2 0.0473(7) 0.0531(7) 0.0449(7) 0.0043(7) -0.0183(5) -0.0024(7) S3 0.0617(8) 0.0424(8) 0.0536(9) 0.0016(7) -0.0212(7) 0.0126(7) S4 0.0712(9) 0.0346(7) 0.0723(10) 0.0076(7) -0.0204(8) -0.0005(7) S5 0.0733(9) 0.0398(8) 0.0590(9) -0.0030(7) -0.0168(7) -0.0049(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C15 1.386(3) . ? C1 C2 1.4205(10) . ? C1 S1 1.751(7) . ? C2 C17 1.376(3) . ? C2 C3 1.460(8) . ? C3 C4 1.384(3) . ? C3 S2 1.816(7) . ? C4 C5 1.456(8) . ? C4 S3 1.738(7) . ? C5 C18 1.376(3) . ? C5 C6 1.434(8) . ? C6 C7 1.384(3) . ? C6 S4 1.786(7) . ? C7 C8 1.435(9) . ? C7 S5 1.735(7) . ? C8 C19 1.375(3) . ? C8 C9 1.442(8) . ? C9 C10 1.384(3) . ? C9 S1 1.809(8) 3_675 ? C10 C11 1.460(9) . ? C10 S2 1.732(8) 3_675 ? C11 C20 1.377(3) . ? C11 C12 1.435(8) . ? C12 C13 1.384(3) . ? C12 S3 1.805(7) 3_675 ? C13 C14 1.436(8) . ? C13 S4 1.753(8) 3_675 ? C14 C16 1.377(3) . ? C14 C15 1.458(8) . ? C15 S5 1.850(8) 3_675 ? C16 C17 1.413(3) . ? C16 C20 1.416(3) . ? C17 C18 1.416(3) . ? C18 C19 1.418(3) . ? C19 C20 1.415(3) . ? C21 C26 1.385(2) . ? C21 C22 1.386(2) . ? C21 S2 1.732(5) . ? C22 C23 1.386(2) . ? C22 H22 0.9300 . ? C23 C24 1.388(2) . ? C23 H23 0.9300 . ? C24 C25 1.384(2) . ? C24 H24 0.9300 . ? C25 C26 1.390(2) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C36 1.351(6) . ? C31 C32 1.366(7) . ? C31 S3 1.777(5) . ? C32 C33 1.392(8) . ? C32 H32 0.9300 . ? C33 C34 1.383(9) . ? C33 H33 0.9300 . ? C34 C35 1.355(9) . ? C34 H34 0.9300 . ? C35 C36 1.354(8) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C41 C42 1.350(7) . ? C41 C46 1.370(7) . ? C41 S4 1.762(5) . ? C42 C43 1.379(8) . ? C42 H42 0.9300 . ? C43 C44 1.394(9) . ? C43 H43 0.9300 . ? C44 C45 1.322(9) . ? C44 H44 0.9300 . ? C45 C46 1.342(8) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? C51 C52 1.353(7) . ? C51 C56 1.363(7) . ? C51 S5 1.778(5) . ? C52 C53 1.355(11) . ? C52 H52 0.9300 . ? C53 C54 1.341(12) . ? C53 H53 0.9300 . ? C54 C55 1.329(11) . ? C54 H54 0.9300 . ? C55 C56 1.372(9) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? C61 C66 1.361(5) . ? C61 C62 1.386(7) . ? C61 S1 1.769(5) . ? C62 C63 1.360(7) . ? C62 H62 0.9300 . ? C63 C64 1.377(8) . ? C63 H63 0.9300 . ? C64 C65 1.363(8) . ? C64 H64 0.9300 . ? C65 C66 1.375(6) . ? C65 H65 0.9300 . ? C66 H66 0.9300 . ? S1 C9 1.809(8) 3_675 ? S2 C10 1.732(8) 3_675 ? S3 C12 1.805(7) 3_675 ? S4 C13 1.753(8) 3_675 ? S5 C15 1.850(8) 3_675 ? 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 C15 C1 C2 124.8(7) . . ? C15 C1 S1 117.6(5) . . ? C2 C1 S1 117.5(5) . . ? C17 C2 C1 111.3(5) . . ? C17 C2 C3 110.5(5) . . ? C1 C2 C3 137.9(6) . . ? C4 C3 C2 122.3(6) . . ? C4 C3 S2 120.3(5) . . ? C2 C3 S2 117.2(4) . . ? C3 C4 C5 125.7(6) . . ? C3 C4 S3 117.3(5) . . ? C5 C4 S3 116.8(5) . . ? C18 C5 C6 112.6(6) . . ? C18 C5 C4 109.1(6) . . ? C6 C5 C4 138.3(6) . . ? C7 C6 C5 121.0(6) . . ? C7 C6 S4 122.1(6) . . ? C5 C6 S4 116.9(5) . . ? C6 C7 C8 125.8(7) . . ? C6 C7 S5 118.6(6) . . ? C8 C7 S5 115.3(5) . . ? C19 C8 C7 110.3(6) . . ? C19 C8 C9 110.2(6) . . ? C7 C8 C9 139.1(6) . . ? C10 C9 C8 124.6(7) . . ? C10 C9 S1 119.1(6) . 3_675 ? C8 C9 S1 116.3(5) . 3_675 ? C9 C10 C11 122.5(7) . . ? C9 C10 S2 120.8(6) . 3_675 ? C11 C10 S2 116.7(5) . 3_675 ? C20 C11 C12 111.0(6) . . ? C20 C11 C10 110.8(6) . . ? C12 C11 C10 138.1(6) . . ? C13 C12 C11 123.1(7) . . ? C13 C12 S3 119.8(6) . 3_675 ? C11 C12 S3 116.8(5) . 3_675 ? C12 C13 C14 124.0(7) . . ? C12 C13 S4 118.5(6) . 3_675 ? C14 C13 S4 117.4(5) . 3_675 ? C16 C14 C13 111.5(6) . . ? C16 C14 C15 110.5(6) . . ? C13 C14 C15 137.5(6) . . ? C1 C15 C14 122.2(7) . . ? C1 C15 S5 119.6(5) . 3_675 ? C14 C15 S5 117.9(5) . 3_675 ? C14 C16 C17 126.1(6) . . ? C14 C16 C20 123.2(5) . . ? C17 C16 C20 108.3(4) . . ? C2 C17 C16 123.5(5) . . ? C2 C17 C18 125.9(5) . . ? C16 C17 C18 108.3(5) . . ? C5 C18 C17 125.2(5) . . ? C5 C18 C19 124.5(5) . . ? C17 C18 C19 107.2(5) . . ? C8 C19 C20 126.1(5) . . ? C8 C19 C18 124.1(5) . . ? C20 C19 C18 108.8(5) . . ? C11 C20 C19 124.1(5) . . ? C11 C20 C16 125.8(5) . . ? C19 C20 C16 107.4(5) . . ? C26 C21 C22 117.9(5) . . ? C26 C21 S2 120.6(4) . . ? C22 C21 S2 121.0(4) . . ? C23 C22 C21 121.2(6) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 120.7(7) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C25 C24 C23 118.2(7) . . ? C25 C24 H24 120.9 . . ? C23 C24 H24 120.9 . . ? C24 C25 C26 120.9(6) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C21 C26 C25 120.9(5) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? C36 C31 C32 119.9(5) . . ? C36 C31 S3 117.8(4) . . ? C32 C31 S3 121.9(4) . . ? C31 C32 C33 120.6(6) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C34 C33 C32 117.8(7) . . ? C34 C33 H33 121.1 . . ? C32 C33 H33 121.1 . . ? C35 C34 C33 120.1(7) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C36 121.3(7) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C31 C36 C35 120.0(6) . . ? C31 C36 H36 120.0 . . ? C35 C36 H36 120.0 . . ? C42 C41 C46 119.4(6) . . ? C42 C41 S4 125.3(5) . . ? C46 C41 S4 115.1(5) . . ? C41 C42 C43 120.6(6) . . ? C41 C42 H42 119.7 . . ? C43 C42 H42 119.7 . . ? C42 C43 C44 117.7(7) . . ? C42 C43 H43 121.1 . . ? C44 C43 H43 121.1 . . ? C45 C44 C43 120.7(7) . . ? C45 C44 H44 119.6 . . ? C43 C44 H44 119.6 . . ? C44 C45 C46 121.0(7) . . ? C44 C45 H45 119.5 . . ? C46 C45 H45 119.5 . . ? C45 C46 C41 120.4(7) . . ? C45 C46 H46 119.8 . . ? C41 C46 H46 119.8 . . ? C52 C51 C56 119.7(6) . . ? C52 C51 S5 122.4(5) . . ? C56 C51 S5 117.7(5) . . ? C51 C52 C53 119.8(8) . . ? C51 C52 H52 120.1 . . ? C53 C52 H52 120.1 . . ? C54 C53 C52 120.6(11) . . ? C54 C53 H53 119.7 . . ? C52 C53 H53 119.7 . . ? C55 C54 C53 120.0(11) . . ? C55 C54 H54 120.0 . . ? C53 C54 H54 120.0 . . ? C54 C55 C56 120.9(10) . . ? C54 C55 H55 119.5 . . ? C56 C55 H55 119.5 . . ? C51 C56 C55 118.8(7) . . ? C51 C56 H56 120.6 . . ? C55 C56 H56 120.6 . . ? C66 C61 C62 119.6(4) . . ? C66 C61 S1 118.3(3) . . ? C62 C61 S1 121.9(4) . . ? C63 C62 C61 118.5(6) . . ? C63 C62 H62 120.7 . . ? C61 C62 H62 120.7 . . ? C62 C63 C64 121.9(6) . . ? C62 C63 H63 119.1 . . ? C64 C63 H63 119.1 . . ? C65 C64 C63 119.3(6) . . ? C65 C64 H64 120.4 . . ? C63 C64 H64 120.4 . . ? C64 C65 C66 119.3(5) . . ? C64 C65 H65 120.4 . . ? C66 C65 H65 120.4 . . ? C61 C66 C65 121.4(4) . . ? C61 C66 H66 119.3 . . ? C65 C66 H66 119.3 . . ? C1 S1 C61 103.1(3) . . ? C1 S1 C9 25.7(3) . 3_675 ? C61 S1 C9 101.8(3) . 3_675 ? C21 S2 C10 98.2(3) . 3_675 ? C21 S2 C3 103.1(3) . . ? C10 S2 C3 27.2(3) 3_675 . ? C4 S3 C31 101.2(3) . . ? C4 S3 C12 26.1(3) . 3_675 ? C31 S3 C12 101.3(3) . 3_675 ? C13 S4 C41 106.9(3) 3_675 . ? C13 S4 C6 27.4(3) 3_675 . ? C41 S4 C6 102.9(3) . . ? C7 S5 C51 101.8(3) . . ? C7 S5 C15 25.9(3) . 3_675 ? C51 S5 C15 102.0(3) . 3_675 ? 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 C15 C1 C2 C17 14.1(12) . . . . ? S1 C1 C2 C17 -163.2(6) . . . . ? C15 C1 C2 C3 -159.5(9) . . . . ? S1 C1 C2 C3 23.2(13) . . . . ? C17 C2 C3 C4 -3.7(11) . . . . ? C1 C2 C3 C4 170.0(9) . . . . ? C17 C2 C3 S2 -178.8(5) . . . . ? C1 C2 C3 S2 -5.2(13) . . . . ? C2 C3 C4 C5 -6.0(13) . . . . ? S2 C3 C4 C5 169.0(6) . . . . ? C2 C3 C4 S3 168.6(6) . . . . ? S2 C3 C4 S3 -16.4(10) . . . . ? C3 C4 C5 C18 12.2(11) . . . . ? S3 C4 C5 C18 -162.4(6) . . . . ? C3 C4 C5 C6 -163.7(9) . . . . ? S3 C4 C5 C6 21.7(13) . . . . ? C18 C5 C6 C7 -2.8(11) . . . . ? C4 C5 C6 C7 173.0(9) . . . . ? C18 C5 C6 S4 179.6(6) . . . . ? C4 C5 C6 S4 -4.6(13) . . . . ? C5 C6 C7 C8 -9.7(14) . . . . ? S4 C6 C7 C8 167.9(6) . . . . ? C5 C6 C7 S5 163.3(6) . . . . ? S4 C6 C7 S5 -19.2(10) . . . . ? C6 C7 C8 C19 13.9(12) . . . . ? S5 C7 C8 C19 -159.3(6) . . . . ? C6 C7 C8 C9 -158.8(10) . . . . ? S5 C7 C8 C9 28.1(14) . . . . ? C19 C8 C9 C10 2.1(12) . . . . ? C7 C8 C9 C10 174.8(9) . . . . ? C19 C8 C9 S1 -177.8(6) . . . 3_675 ? C7 C8 C9 S1 -5.1(14) . . . 3_675 ? C8 C9 C10 C11 -11.4(13) . . . . ? S1 C9 C10 C11 168.5(6) 3_675 . . . ? C8 C9 C10 S2 167.7(6) . . . 3_675 ? S1 C9 C10 S2 -12.4(10) 3_675 . . 3_675 ? C9 C10 C11 C20 15.2(11) . . . . ? S2 C10 C11 C20 -164.0(6) 3_675 . . . ? C9 C10 C11 C12 -162.1(10) . . . . ? S2 C10 C11 C12 18.7(13) 3_675 . . . ? C20 C11 C12 C13 -4.4(12) . . . . ? C10 C11 C12 C13 172.9(9) . . . . ? C20 C11 C12 S3 -178.3(6) . . . 3_675 ? C10 C11 C12 S3 -0.9(14) . . . 3_675 ? C11 C12 C13 C14 -5.8(13) . . . . ? S3 C12 C13 C14 167.9(6) 3_675 . . . ? C11 C12 C13 S4 172.0(6) . . . 3_675 ? S3 C12 C13 S4 -14.3(9) 3_675 . . 3_675 ? C12 C13 C14 C16 12.4(11) . . . . ? S4 C13 C14 C16 -165.4(6) 3_675 . . . ? C12 C13 C14 C15 -159.4(9) . . . . ? S4 C13 C14 C15 22.8(13) 3_675 . . . ? C2 C1 C15 C14 -11.5(13) . . . . ? S1 C1 C15 C14 165.9(6) . . . . ? C2 C1 C15 S5 163.3(6) . . . 3_675 ? S1 C1 C15 S5 -19.4(10) . . . 3_675 ? C16 C14 C15 C1 1.3(11) . . . . ? C13 C14 C15 C1 173.1(9) . . . . ? C16 C14 C15 S5 -173.5(6) . . . 3_675 ? C13 C14 C15 S5 -1.7(13) . . . 3_675 ? C13 C14 C16 C17 -169.5(7) . . . . ? C15 C14 C16 C17 4.6(11) . . . . ? C13 C14 C16 C20 -9.4(11) . . . . ? C15 C14 C16 C20 164.7(7) . . . . ? C1 C2 C17 C16 -8.0(11) . . . . ? C3 C2 C17 C16 167.4(7) . . . . ? C1 C2 C17 C18 -169.2(8) . . . . ? C3 C2 C17 C18 6.3(11) . . . . ? C14 C16 C17 C2 -1.0(13) . . . . ? C20 C16 C17 C2 -163.5(7) . . . . ? C14 C16 C17 C18 163.0(8) . . . . ? C20 C16 C17 C18 0.5(9) . . . . ? C6 C5 C18 C17 167.4(7) . . . . ? C4 C5 C18 C17 -9.6(11) . . . . ? C6 C5 C18 C19 9.7(11) . . . . ? C4 C5 C18 C19 -167.3(7) . . . . ? C2 C17 C18 C5 0.9(13) . . . . ? C16 C17 C18 C5 -162.6(8) . . . . ? C2 C17 C18 C19 161.7(8) . . . . ? C16 C17 C18 C19 -1.8(9) . . . . ? C7 C8 C19 C20 -173.1(8) . . . . ? C9 C8 C19 C20 1.8(11) . . . . ? C7 C8 C19 C18 -6.7(11) . . . . ? C9 C8 C19 C18 168.3(7) . . . . ? C5 C18 C19 C8 -5.0(13) . . . . ? C17 C18 C19 C8 -166.0(8) . . . . ? C5 C18 C19 C20 163.5(7) . . . . ? C17 C18 C19 C20 2.4(9) . . . . ? C12 C11 C20 C19 166.4(7) . . . . ? C10 C11 C20 C19 -11.7(11) . . . . ? C12 C11 C20 C16 7.5(12) . . . . ? C10 C11 C20 C16 -170.6(7) . . . . ? C8 C19 C20 C11 3.9(13) . . . . ? C18 C19 C20 C11 -164.3(8) . . . . ? C8 C19 C20 C16 166.0(8) . . . . ? C18 C19 C20 C16 -2.2(9) . . . . ? C14 C16 C20 C11 -0.4(13) . . . . ? C17 C16 C20 C11 162.8(8) . . . . ? C14 C16 C20 C19 -162.1(7) . . . . ? C17 C16 C20 C19 1.0(9) . . . . ? C26 C21 C22 C23 -4.3(9) . . . . ? S2 C21 C22 C23 -176.3(6) . . . . ? C21 C22 C23 C24 4.0(12) . . . . ? C22 C23 C24 C25 -1.4(12) . . . . ? C23 C24 C25 C26 -0.6(11) . . . . ? C22 C21 C26 C25 2.2(8) . . . . ? S2 C21 C26 C25 174.2(4) . . . . ? C24 C25 C26 C21 0.2(9) . . . . ? C36 C31 C32 C33 6.2(9) . . . . ? S3 C31 C32 C33 179.6(5) . . . . ? C31 C32 C33 C34 -3.5(11) . . . . ? C32 C33 C34 C35 -1.2(12) . . . . ? C33 C34 C35 C36 3.4(13) . . . . ? C32 C31 C36 C35 -4.0(9) . . . . ? S3 C31 C36 C35 -177.7(5) . . . . ? C34 C35 C36 C31 -0.7(11) . . . . ? C46 C41 C42 C43 -2.6(10) . . . . ? S4 C41 C42 C43 -177.7(5) . . . . ? C41 C42 C43 C44 0.2(11) . . . . ? C42 C43 C44 C45 3.1(13) . . . . ? C43 C44 C45 C46 -3.9(14) . . . . ? C44 C45 C46 C41 1.4(13) . . . . ? C42 C41 C46 C45 1.9(10) . . . . ? S4 C41 C46 C45 177.5(6) . . . . ? C56 C51 C52 C53 5.4(11) . . . . ? S5 C51 C52 C53 -178.8(6) . . . . ? C51 C52 C53 C54 -4.9(15) . . . . ? C52 C53 C54 C55 0.9(18) . . . . ? C53 C54 C55 C56 2.8(17) . . . . ? C52 C51 C56 C55 -1.8(9) . . . . ? S5 C51 C56 C55 -177.8(5) . . . . ? C54 C55 C56 C51 -2.2(12) . . . . ? C66 C61 C62 C63 3.2(8) . . . . ? S1 C61 C62 C63 177.8(5) . . . . ? C61 C62 C63 C64 -2.6(10) . . . . ? C62 C63 C64 C65 0.9(12) . . . . ? C63 C64 C65 C66 0.3(11) . . . . ? C62 C61 C66 C65 -2.2(6) . . . . ? S1 C61 C66 C65 -177.0(4) . . . . ? C64 C65 C66 C61 0.4(8) . . . . ? C15 C1 S1 C61 -126.5(7) . . . . ? C2 C1 S1 C61 51.0(7) . . . . ? C15 C1 S1 C9 143.6(13) . . . 3_675 ? C2 C1 S1 C9 -38.9(7) . . . 3_675 ? C66 C61 S1 C1 -159.8(3) . . . . ? C62 C61 S1 C1 25.4(5) . . . . ? C66 C61 S1 C9 -133.6(4) . . . 3_675 ? C62 C61 S1 C9 51.7(5) . . . 3_675 ? C26 C21 S2 C10 157.0(5) . . . 3_675 ? C22 C21 S2 C10 -31.2(5) . . . 3_675 ? C26 C21 S2 C3 129.8(4) . . . . ? C22 C21 S2 C3 -58.5(5) . . . . ? C4 C3 S2 C21 -61.7(7) . . . . ? C2 C3 S2 C21 113.6(6) . . . . ? C4 C3 S2 C10 -144.2(12) . . . 3_675 ? C2 C3 S2 C10 31.1(7) . . . 3_675 ? C3 C4 S3 C31 -122.7(6) . . . . ? C5 C4 S3 C31 52.3(6) . . . . ? C3 C4 S3 C12 144.3(13) . . . 3_675 ? C5 C4 S3 C12 -40.7(7) . . . 3_675 ? C36 C31 S3 C4 -156.9(5) . . . . ? C32 C31 S3 C4 29.5(5) . . . . ? C36 C31 S3 C12 -130.3(5) . . . 3_675 ? C32 C31 S3 C12 56.1(5) . . . 3_675 ? C42 C41 S4 C13 -13.0(6) . . . 3_675 ? C46 C41 S4 C13 171.7(5) . . . 3_675 ? C42 C41 S4 C6 -41.1(6) . . . . ? C46 C41 S4 C6 143.6(5) . . . . ? C7 C6 S4 C13 -146.0(13) . . . 3_675 ? C5 C6 S4 C13 31.6(7) . . . 3_675 ? C7 C6 S4 C41 -44.0(8) . . . . ? C5 C6 S4 C41 133.6(6) . . . . ? C6 C7 S5 C51 -120.7(7) . . . . ? C8 C7 S5 C51 53.0(7) . . . . ? C6 C7 S5 C15 146.0(14) . . . 3_675 ? C8 C7 S5 C15 -40.3(8) . . . 3_675 ? C52 C51 S5 C7 21.1(6) . . . . ? C56 C51 S5 C7 -163.0(5) . . . . ? C52 C51 S5 C15 47.6(6) . . . 3_675 ? C56 C51 S5 C15 -136.5(5) . . . 3_675 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.282 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.063