# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl #TrackingRef '10TBPQ.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C58 H40 N4, 2(C H Cl3)' _chemical_formula_sum 'C60 H42 Cl6 N4' _chemical_formula_weight 1031.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 17.4912(6) _cell_length_b 12.3477(4) _cell_length_c 23.7674(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.3020(10) _cell_angle_gamma 90.00 _cell_volume 5124.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 18481 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 25.34 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.380 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9453 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35665 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 25.34 _reflns_number_total 4681 _reflns_number_gt 3939 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1110P)^2^+9.2306P] 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 4681 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1949 _refine_ls_wR_factor_gt 0.1881 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.40106(14) 0.3633(2) 0.07061(11) 0.0732(6) Uani 0.688(4) 1 d P A 1 Cl2 Cl 0.47751(13) 0.53626(12) 0.13127(8) 0.0813(7) Uani 0.688(4) 1 d P A 1 Cl3 Cl 0.4765(2) 0.32611(17) 0.18069(7) 0.0936(9) Uani 0.688(4) 1 d P A 1 C30 C 0.4753(8) 0.3970(9) 0.1152(5) 0.048(2) Uani 0.688(4) 1 d P A 1 H30 H 0.5236 0.3787 0.0966 0.057 Uiso 0.688(4) 1 calc PR A 1 Cl4 Cl 0.4328(2) 0.2785(4) 0.17756(14) 0.0646(12) Uani 0.312(4) 1 d P A 2 Cl5 Cl 0.3894(3) 0.4087(5) 0.0840(3) 0.0801(15) Uani 0.312(4) 1 d P A 2 Cl6 Cl 0.5213(2) 0.4660(5) 0.1536(2) 0.105(2) Uani 0.312(4) 1 d P A 2 C31 C 0.4724(14) 0.370(2) 0.1285(11) 0.059(8) Uani 0.312(4) 1 d P A 2 H31 H 0.5063 0.3260 0.1047 0.071 Uiso 0.312(4) 1 calc PR A 2 N1 N 0.21406(13) -0.19956(17) -0.11736(9) 0.0363(5) Uani 1 1 d . . . N2 N 0.09380(13) -0.19429(18) 0.03183(10) 0.0403(6) Uani 1 1 d . . . C1 C 0.48000(15) -0.0408(2) -0.11916(11) 0.0371(6) Uani 1 1 d . . . H1 H 0.4696 -0.1199 -0.1244 0.044 Uiso 1 1 calc R . . C2 C 0.41837(13) 0.0154(2) -0.08789(10) 0.0281(5) Uani 1 1 d . . . C3 C 0.35771(13) -0.03427(19) -0.06416(9) 0.0254(5) Uani 1 1 d . . . H3 H 0.3496 -0.1099 -0.0688 0.031 Uiso 1 1 calc R . . C4 C 0.30761(12) 0.02818(18) -0.03288(9) 0.0222(5) Uani 1 1 d . . . C5 C 0.24740(13) -0.02206(17) -0.00065(9) 0.0224(5) Uani 1 1 d . . . C6 C 0.23806(12) 0.02812(18) 0.05509(9) 0.0220(5) Uani 1 1 d . . . C7 C 0.22624(13) -0.03319(19) 0.10352(10) 0.0249(5) Uani 1 1 d . . . H7 H 0.2181 -0.1091 0.1005 0.030 Uiso 1 1 calc R . . C8 C 0.22643(14) 0.0166(2) 0.15530(10) 0.0283(5) Uani 1 1 d . . . C9 C 0.21877(17) -0.0378(2) 0.21164(11) 0.0394(6) Uani 1 1 d . . . H9 H 0.2095 -0.1174 0.2080 0.047 Uiso 1 1 calc R . . C10 C 0.15405(19) 0.0209(3) 0.24050(12) 0.0540(9) Uani 1 1 d . . . H10 H 0.1110 -0.0153 0.2544 0.065 Uiso 1 1 calc R . . C11 C 0.16501(19) 0.1325(3) 0.24421(12) 0.0512(8) Uani 1 1 d . . . H11 H 0.1298 0.1808 0.2601 0.061 Uiso 1 1 calc R . . C12 C 0.24004(16) 0.1687(2) 0.21989(10) 0.0370(6) Uani 1 1 d . . . H12 H 0.2478 0.2488 0.2226 0.044 Uiso 1 1 calc R . . C13 C 0.23831(13) 0.1287(2) 0.15986(10) 0.0276(5) Uani 1 1 d . . . C14 C 0.24896(13) 0.19023(19) 0.11246(10) 0.0258(5) Uani 1 1 d . . . H14 H 0.2564 0.2662 0.1159 0.031 Uiso 1 1 calc R . . C15 C 0.24889(12) 0.14110(17) 0.05937(9) 0.0223(5) Uani 1 1 d . . . C16 C 0.26522(12) 0.20097(18) 0.00722(9) 0.0222(5) Uani 1 1 d . . . C17 C 0.31899(12) 0.14013(18) -0.02727(9) 0.0235(5) Uani 1 1 d . . . C18 C 0.38183(13) 0.18861(19) -0.05114(10) 0.0264(5) Uani 1 1 d . . . H18 H 0.3906 0.2641 -0.0468 0.032 Uiso 1 1 calc R . . C19 C 0.43098(14) 0.1263(2) -0.08103(10) 0.0289(5) Uani 1 1 d . . . C20 C 0.50355(15) 0.1644(2) -0.10642(12) 0.0389(6) Uani 1 1 d . . . H20 H 0.5118 0.2442 -0.1020 0.047 Uiso 1 1 calc R . . C21 C 0.49828(17) 0.1288(4) -0.16834(13) 0.0571(10) Uani 1 1 d . . . H21 H 0.5029 0.1773 -0.1990 0.068 Uiso 1 1 calc R . . C22 C 0.48607(17) 0.0180(3) -0.17494(12) 0.0532(9) Uani 1 1 d . . . H22 H 0.4820 -0.0171 -0.2105 0.064 Uiso 1 1 calc R . . C23 C 0.55625(15) -0.0194(2) -0.08538(12) 0.0384(6) Uani 1 1 d . . . H23A H 0.5551 -0.0542 -0.0479 0.046 Uiso 1 1 calc R . . H23B H 0.5988 -0.0518 -0.1053 0.046 Uiso 1 1 calc R . . C24 C 0.56968(14) 0.0972(2) -0.07818(12) 0.0351(6) Uani 1 1 d . . . H24A H 0.6183 0.1171 -0.0949 0.042 Uiso 1 1 calc R . . H24B H 0.5748 0.1146 -0.0375 0.042 Uiso 1 1 calc R . . C25 C 0.29245(19) -0.0116(3) 0.24771(12) 0.0463(7) Uani 1 1 d . . . H25A H 0.2889 -0.0430 0.2858 0.056 Uiso 1 1 calc R . . H25B H 0.3368 -0.0452 0.2304 0.056 Uiso 1 1 calc R . . C26 C 0.30442(19) 0.1047(2) 0.25240(12) 0.0447(7) Uani 1 1 d . . . H26A H 0.3543 0.1235 0.2373 0.054 Uiso 1 1 calc R . . H26B H 0.3063 0.1258 0.2926 0.054 Uiso 1 1 calc R . . C27 C 0.20499(13) -0.10825(18) -0.01983(10) 0.0250(5) Uani 1 1 d . . . C28 C 0.21163(14) -0.15694(19) -0.07477(10) 0.0279(5) Uani 1 1 d . . . C29 C 0.14376(14) -0.15444(19) 0.01014(10) 0.0295(5) 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 Cl1 0.0497(10) 0.0769(16) 0.0906(14) -0.0125(11) -0.0167(8) -0.0081(10) Cl2 0.1104(15) 0.0436(8) 0.0873(11) 0.0017(7) -0.0162(10) -0.0107(8) Cl3 0.175(3) 0.0575(11) 0.0497(9) 0.0044(7) 0.0152(12) 0.0303(14) C30 0.052(4) 0.057(4) 0.033(5) -0.002(4) 0.000(4) 0.011(3) Cl4 0.066(2) 0.077(3) 0.0505(16) -0.0176(16) 0.0001(14) 0.0233(18) Cl5 0.058(2) 0.077(4) 0.101(4) 0.004(3) -0.028(2) 0.003(2) Cl6 0.068(2) 0.155(5) 0.094(3) -0.042(3) 0.004(2) -0.049(3) C31 0.034(9) 0.11(2) 0.034(11) 0.004(9) -0.014(7) 0.048(11) N1 0.0485(13) 0.0281(11) 0.0322(12) -0.0032(9) 0.0001(9) -0.0020(9) N2 0.0416(13) 0.0343(13) 0.0459(13) -0.0064(10) 0.0117(11) -0.0095(10) C1 0.0303(13) 0.0470(16) 0.0347(14) -0.0092(12) 0.0088(11) 0.0039(11) C2 0.0270(12) 0.0345(13) 0.0227(11) -0.0012(10) 0.0010(9) 0.0056(10) C3 0.0274(11) 0.0246(12) 0.0241(11) -0.0038(9) -0.0003(9) 0.0041(9) C4 0.0240(11) 0.0208(11) 0.0219(11) 0.0009(8) 0.0004(8) 0.0033(8) C5 0.0251(11) 0.0182(11) 0.0239(11) 0.0022(8) 0.0016(8) 0.0056(8) C6 0.0195(10) 0.0196(11) 0.0270(11) 0.0011(9) 0.0019(8) 0.0029(8) C7 0.0260(11) 0.0207(11) 0.0279(12) 0.0031(9) 0.0016(9) -0.0001(9) C8 0.0290(12) 0.0281(12) 0.0277(12) 0.0042(10) 0.0010(9) 0.0011(10) C9 0.0520(16) 0.0389(15) 0.0270(13) 0.0069(11) 0.0010(11) -0.0060(12) C10 0.0502(18) 0.082(3) 0.0312(15) 0.0086(15) 0.0114(13) -0.0021(17) C11 0.0546(19) 0.069(2) 0.0311(15) -0.0061(14) 0.0114(13) 0.0107(16) C12 0.0486(15) 0.0373(14) 0.0247(12) -0.0040(11) -0.0008(11) 0.0078(12) C13 0.0283(12) 0.0291(13) 0.0253(12) -0.0026(9) -0.0003(9) 0.0065(9) C14 0.0274(11) 0.0199(11) 0.0299(12) -0.0015(9) 0.0007(9) 0.0040(9) C15 0.0214(11) 0.0179(11) 0.0276(12) 0.0011(9) 0.0012(9) 0.0032(8) C16 0.0212(10) 0.0175(10) 0.0280(11) -0.0003(8) 0.0015(8) 0.0003(8) C17 0.0237(11) 0.0218(11) 0.0248(11) 0.0013(9) 0.0006(9) 0.0038(9) C18 0.0263(11) 0.0204(11) 0.0325(12) 0.0083(9) 0.0017(9) 0.0019(9) C19 0.0270(12) 0.0327(13) 0.0274(12) 0.0098(10) 0.0039(9) 0.0050(10) C20 0.0313(13) 0.0435(15) 0.0432(15) 0.0144(12) 0.0144(11) 0.0041(11) C21 0.0374(16) 0.102(3) 0.0331(15) 0.0270(17) 0.0114(12) 0.0103(17) C22 0.0363(15) 0.099(3) 0.0250(14) -0.0065(15) 0.0063(11) 0.0017(16) C23 0.0305(13) 0.0476(16) 0.0372(14) -0.0048(12) 0.0025(11) 0.0116(11) C24 0.0270(12) 0.0401(15) 0.0385(14) 0.0008(11) 0.0036(10) 0.0020(11) C25 0.0524(17) 0.0533(18) 0.0324(14) 0.0119(13) -0.0051(12) 0.0025(14) C26 0.0535(18) 0.0477(17) 0.0317(14) 0.0000(12) -0.0076(12) 0.0043(14) C27 0.0297(12) 0.0182(11) 0.0272(11) 0.0005(9) 0.0034(9) 0.0012(9) C28 0.0315(12) 0.0190(11) 0.0329(13) 0.0013(10) 0.0004(10) -0.0009(9) C29 0.0337(13) 0.0219(12) 0.0329(13) -0.0054(10) 0.0012(10) -0.0007(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C30 1.681(13) . ? Cl2 C30 1.762(12) . ? Cl3 C30 1.784(10) . ? C30 H30 1.0000 . ? Cl4 C31 1.79(2) . ? Cl5 C31 1.81(2) . ? Cl6 C31 1.56(3) . ? C31 H31 1.0000 . ? N1 C28 1.144(3) . ? N2 C29 1.151(3) . ? C1 C2 1.513(3) . ? C1 C22 1.521(4) . ? C1 C23 1.540(4) . ? C1 H1 1.0000 . ? C2 C3 1.374(3) . ? C2 C19 1.396(4) . ? C3 C4 1.411(3) . ? C3 H3 0.9500 . ? C4 C17 1.402(3) . ? C4 C5 1.474(3) . ? C5 C27 1.361(3) . ? C5 C6 1.480(3) . ? C6 C7 1.403(3) . ? C6 C15 1.411(3) . ? C7 C8 1.375(3) . ? C7 H7 0.9500 . ? C8 C13 1.404(4) . ? C8 C9 1.511(3) . ? C9 C10 1.538(4) . ? C9 C25 1.540(4) . ? C9 H9 1.0000 . ? C10 C11 1.393(5) . ? C10 H10 0.9500 . ? C11 C12 1.531(4) . ? C11 H11 0.9500 . ? C12 C13 1.508(3) . ? C12 C26 1.546(4) . ? C12 H12 1.0000 . ? C13 C14 1.380(3) . ? C14 C15 1.400(3) . ? C14 H14 0.9500 . ? C15 C16 1.485(3) . ? C16 C16 1.359(4) 7 ? C16 C17 1.487(3) . ? C17 C18 1.400(3) . ? C18 C19 1.381(3) . ? C18 H18 0.9500 . ? C19 C20 1.512(3) . ? C20 C21 1.533(4) . ? C20 C24 1.545(4) . ? C20 H20 1.0000 . ? C21 C22 1.392(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.467(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.455(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C29 1.438(3) . ? C27 C28 1.448(3) . ? 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 Cl1 C30 Cl2 112.6(6) . . ? Cl1 C30 Cl3 113.5(7) . . ? Cl2 C30 Cl3 106.9(6) . . ? Cl1 C30 H30 107.9 . . ? Cl2 C30 H30 107.9 . . ? Cl3 C30 H30 107.9 . . ? Cl6 C31 Cl4 117.0(16) . . ? Cl6 C31 Cl5 114.9(15) . . ? Cl4 C31 Cl5 102.8(13) . . ? Cl6 C31 H31 107.2 . . ? Cl4 C31 H31 107.2 . . ? Cl5 C31 H31 107.2 . . ? C2 C1 C22 107.3(2) . . ? C2 C1 C23 106.6(2) . . ? C22 C1 C23 105.7(2) . . ? C2 C1 H1 112.3 . . ? C22 C1 H1 112.3 . . ? C23 C1 H1 112.3 . . ? C3 C2 C19 120.7(2) . . ? C3 C2 C1 125.9(2) . . ? C19 C2 C1 113.3(2) . . ? C2 C3 C4 119.4(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C17 C4 C3 120.0(2) . . ? C17 C4 C5 117.85(19) . . ? C3 C4 C5 121.9(2) . . ? C27 C5 C4 123.1(2) . . ? C27 C5 C6 122.8(2) . . ? C4 C5 C6 114.08(19) . . ? C7 C6 C15 120.0(2) . . ? C7 C6 C5 122.5(2) . . ? C15 C6 C5 117.21(19) . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C13 120.2(2) . . ? C7 C8 C9 126.8(2) . . ? C13 C8 C9 113.0(2) . . ? C8 C9 C10 106.9(2) . . ? C8 C9 C25 106.6(2) . . ? C10 C9 C25 105.5(2) . . ? C8 C9 H9 112.4 . . ? C10 C9 H9 112.4 . . ? C25 C9 H9 112.4 . . ? C11 C10 C9 113.1(3) . . ? C11 C10 H10 123.5 . . ? C9 C10 H10 123.5 . . ? C10 C11 C12 112.5(3) . . ? C10 C11 H11 123.8 . . ? C12 C11 H11 123.8 . . ? C13 C12 C11 106.9(2) . . ? C13 C12 C26 106.3(2) . . ? C11 C12 C26 106.1(2) . . ? C13 C12 H12 112.4 . . ? C11 C12 H12 112.4 . . ? C26 C12 H12 112.4 . . ? C14 C13 C8 120.4(2) . . ? C14 C13 C12 126.6(2) . . ? C8 C13 C12 113.0(2) . . ? C13 C14 C15 120.3(2) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C6 119.1(2) . . ? C14 C15 C16 123.1(2) . . ? C6 C15 C16 117.62(19) . . ? C16 C16 C15 124.3(3) 7 . ? C16 C16 C17 124.2(3) 7 . ? C15 C16 C17 111.53(18) . . ? C18 C17 C4 119.6(2) . . ? C18 C17 C16 122.9(2) . . ? C4 C17 C16 117.4(2) . . ? C19 C18 C17 119.8(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C2 120.6(2) . . ? C18 C19 C20 126.4(2) . . ? C2 C19 C20 112.9(2) . . ? C19 C20 C21 106.8(2) . . ? C19 C20 C24 106.5(2) . . ? C21 C20 C24 105.4(2) . . ? C19 C20 H20 112.5 . . ? C21 C20 H20 112.5 . . ? C24 C20 H20 112.5 . . ? C22 C21 C20 113.0(3) . . ? C22 C21 H21 123.5 . . ? C20 C21 H21 123.5 . . ? C21 C22 C1 112.9(3) . . ? C21 C22 H22 123.5 . . ? C1 C22 H22 123.5 . . ? C24 C23 C1 111.0(2) . . ? C24 C23 H23A 109.4 . . ? C1 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? C1 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C20 111.4(2) . . ? C23 C24 H24A 109.3 . . ? C20 C24 H24A 109.3 . . ? C23 C24 H24B 109.3 . . ? C20 C24 H24B 109.3 . . ? H24A C24 H24B 108.0 . . ? C26 C25 C9 111.2(2) . . ? C26 C25 H25A 109.4 . . ? C9 C25 H25A 109.4 . . ? C26 C25 H25B 109.4 . . ? C9 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C25 C26 C12 111.6(2) . . ? C25 C26 H26A 109.3 . . ? C12 C26 H26A 109.3 . . ? C25 C26 H26B 109.3 . . ? C12 C26 H26B 109.3 . . ? H26A C26 H26B 108.0 . . ? C5 C27 C29 123.5(2) . . ? C5 C27 C28 123.8(2) . . ? C29 C27 C28 112.5(2) . . ? N1 C28 C27 176.3(3) . . ? N2 C29 C27 176.7(3) . . ? 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 C22 C1 C2 C3 129.4(3) . . . . ? C23 C1 C2 C3 -117.8(3) . . . . ? C22 C1 C2 C19 -55.0(3) . . . . ? C23 C1 C2 C19 57.8(3) . . . . ? C19 C2 C3 C4 0.4(3) . . . . ? C1 C2 C3 C4 175.7(2) . . . . ? C2 C3 C4 C17 1.4(3) . . . . ? C2 C3 C4 C5 -172.3(2) . . . . ? C17 C4 C5 C27 146.8(2) . . . . ? C3 C4 C5 C27 -39.4(3) . . . . ? C17 C4 C5 C6 -34.4(3) . . . . ? C3 C4 C5 C6 139.4(2) . . . . ? C27 C5 C6 C7 40.2(3) . . . . ? C4 C5 C6 C7 -138.6(2) . . . . ? C27 C5 C6 C15 -145.8(2) . . . . ? C4 C5 C6 C15 35.4(3) . . . . ? C15 C6 C7 C8 -1.0(3) . . . . ? C5 C6 C7 C8 172.8(2) . . . . ? C6 C7 C8 C13 0.1(3) . . . . ? C6 C7 C8 C9 -176.6(2) . . . . ? C7 C8 C9 C10 -127.9(3) . . . . ? C13 C8 C9 C10 55.2(3) . . . . ? C7 C8 C9 C25 119.6(3) . . . . ? C13 C8 C9 C25 -57.3(3) . . . . ? C8 C9 C10 C11 -54.1(3) . . . . ? C25 C9 C10 C11 59.1(3) . . . . ? C9 C10 C11 C12 -1.5(4) . . . . ? C10 C11 C12 C13 56.4(3) . . . . ? C10 C11 C12 C26 -56.8(3) . . . . ? C7 C8 C13 C14 0.8(4) . . . . ? C9 C8 C13 C14 177.9(2) . . . . ? C7 C8 C13 C12 -177.5(2) . . . . ? C9 C8 C13 C12 -0.4(3) . . . . ? C11 C12 C13 C14 126.3(3) . . . . ? C26 C12 C13 C14 -120.7(3) . . . . ? C11 C12 C13 C8 -55.5(3) . . . . ? C26 C12 C13 C8 57.5(3) . . . . ? C8 C13 C14 C15 -0.7(3) . . . . ? C12 C13 C14 C15 177.4(2) . . . . ? C13 C14 C15 C6 -0.2(3) . . . . ? C13 C14 C15 C16 -175.7(2) . . . . ? C7 C6 C15 C14 1.1(3) . . . . ? C5 C6 C15 C14 -173.0(2) . . . . ? C7 C6 C15 C16 176.85(19) . . . . ? C5 C6 C15 C16 2.7(3) . . . . ? C14 C15 C16 C16 -45.4(4) . . . 7 ? C6 C15 C16 C16 139.0(3) . . . 7 ? C14 C15 C16 C17 134.7(2) . . . . ? C6 C15 C16 C17 -40.9(3) . . . . ? C3 C4 C17 C18 -2.3(3) . . . . ? C5 C4 C17 C18 171.6(2) . . . . ? C3 C4 C17 C16 -178.7(2) . . . . ? C5 C4 C17 C16 -4.8(3) . . . . ? C16 C16 C17 C18 45.8(4) 7 . . . ? C15 C16 C17 C18 -134.2(2) . . . . ? C16 C16 C17 C4 -137.9(3) 7 . . . ? C15 C16 C17 C4 42.1(3) . . . . ? C4 C17 C18 C19 1.5(3) . . . . ? C16 C17 C18 C19 177.7(2) . . . . ? C17 C18 C19 C2 0.3(4) . . . . ? C17 C18 C19 C20 -176.2(2) . . . . ? C3 C2 C19 C18 -1.2(4) . . . . ? C1 C2 C19 C18 -177.1(2) . . . . ? C3 C2 C19 C20 175.7(2) . . . . ? C1 C2 C19 C20 -0.1(3) . . . . ? C18 C19 C20 C21 -128.3(3) . . . . ? C2 C19 C20 C21 55.0(3) . . . . ? C18 C19 C20 C24 119.5(3) . . . . ? C2 C19 C20 C24 -57.2(3) . . . . ? C19 C20 C21 C22 -55.4(3) . . . . ? C24 C20 C21 C22 57.6(3) . . . . ? C20 C21 C22 C1 0.6(4) . . . . ? C2 C1 C22 C21 54.4(3) . . . . ? C23 C1 C22 C21 -59.1(3) . . . . ? C2 C1 C23 C24 -56.4(3) . . . . ? C22 C1 C23 C24 57.5(3) . . . . ? C1 C23 C24 C20 0.1(3) . . . . ? C19 C20 C24 C23 56.3(3) . . . . ? C21 C20 C24 C23 -56.9(3) . . . . ? C8 C9 C25 C26 56.4(3) . . . . ? C10 C9 C25 C26 -57.0(3) . . . . ? C9 C25 C26 C12 -0.1(4) . . . . ? C13 C12 C26 C25 -56.4(3) . . . . ? C11 C12 C26 C25 57.1(3) . . . . ? C4 C5 C27 C29 -176.9(2) . . . . ? C6 C5 C27 C29 4.3(4) . . . . ? C4 C5 C27 C28 -3.0(4) . . . . ? C6 C5 C27 C28 178.3(2) . . . . ? C5 C27 C28 N1 176(100) . . . . ? C29 C27 C28 N1 -9(4) . . . . ? C5 C27 C29 N2 169(5) . . . . ? C28 C27 C29 N2 -5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.912 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 923849' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl2 #TrackingRef '2PQ_C.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H24 O2, C H Cl3' _chemical_formula_sum 'C45 H25 Cl3 O2' _chemical_formula_weight 704.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 24.8385(6) _cell_length_b 11.3087(2) _cell_length_c 12.6953(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.6680(10) _cell_angle_gamma 90.00 _cell_volume 3290.54(13) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 13900 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9388 _exptl_absorpt_correction_T_max 0.9566 _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16054 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3763 _reflns_number_gt 3484 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+3.1965P] 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 3763 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1529 _refine_ls_wR_factor_gt 0.1496 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.06064(8) 0.63529(18) 0.27183(17) 0.0373(4) Uani 0.50 1 d P A -1 Cl2 Cl 0.02710(6) 0.54095(10) 0.44775(10) 0.0593(4) Uani 0.50 1 d P A -1 Cl3 Cl -0.06185(18) 0.6365(4) 0.2265(5) 0.1044(16) Uani 0.50 1 d P A -1 C23 C 0.00945(15) 0.5597(3) 0.3003(4) 0.0414(9) Uani 0.50 1 d P A -1 H22 H 0.0063 0.4793 0.2655 0.050 Uiso 0.50 1 calc PR A -1 O1 O 0.07709(5) 0.35059(10) 0.21255(9) 0.0223(3) Uani 1 1 d . . . C1 C 0.11723(6) 0.29280(12) 0.27917(11) 0.0165(3) Uani 1 1 d . . . C2 C 0.16610(6) 0.24747(12) 0.24953(11) 0.0157(3) Uani 1 1 d . . . C3 C 0.15776(6) 0.23289(12) 0.13640(11) 0.0168(3) Uani 1 1 d . . . H3 H 0.1235 0.2635 0.0785 0.020 Uiso 1 1 calc R . . C4 C 0.19946(6) 0.17313(12) 0.10526(11) 0.0167(3) Uani 1 1 d . . . C5 C 0.19136(6) 0.15225(13) -0.01043(11) 0.0197(3) Uani 1 1 d . . . H5 H 0.1567 0.1785 -0.0702 0.024 Uiso 1 1 calc R . . C6 C 0.23321(7) 0.09454(13) -0.03612(12) 0.0220(3) Uani 1 1 d . . . H6 H 0.2275 0.0819 -0.1137 0.026 Uiso 1 1 calc R . . C7 C 0.28492(6) 0.05348(13) 0.05173(13) 0.0216(3) Uani 1 1 d . . . H7 H 0.3138 0.0143 0.0326 0.026 Uiso 1 1 calc R . . C8 C 0.29363(6) 0.06987(12) 0.16417(12) 0.0192(3) Uani 1 1 d . . . H8 H 0.3281 0.0407 0.2225 0.023 Uiso 1 1 calc R . . C9 C 0.25125(6) 0.13038(12) 0.19377(11) 0.0165(3) Uani 1 1 d . . . C10 C 0.25973(6) 0.14945(12) 0.30932(11) 0.0158(3) Uani 1 1 d . . . H10 H 0.2944 0.1213 0.3680 0.019 Uiso 1 1 calc R . . C11 C 0.21884(6) 0.20796(12) 0.33853(11) 0.0151(3) Uani 1 1 d . . . C12 C 0.22537(6) 0.22895(11) 0.45847(11) 0.0148(3) Uani 1 1 d . . . C13 C 0.17030(6) 0.20436(12) 0.47536(11) 0.0152(3) Uani 1 1 d . . . C14 C 0.16776(6) 0.14108(12) 0.56569(11) 0.0163(3) Uani 1 1 d . . . H14 H 0.2024 0.1073 0.6197 0.020 Uiso 1 1 calc R . . C15 C 0.11412(6) 0.12531(12) 0.57957(11) 0.0169(3) Uani 1 1 d . . . C16 C 0.11010(6) 0.05683(13) 0.67022(12) 0.0198(3) Uani 1 1 d . . . H16 H 0.1438 0.0187 0.7228 0.024 Uiso 1 1 calc R . . C17 C 0.05767(7) 0.04564(14) 0.68212(13) 0.0245(3) Uani 1 1 d . . . H17 H 0.0553 -0.0011 0.7424 0.029 Uiso 1 1 calc R . . C18 C 0.00720(7) 0.10293(16) 0.60573(14) 0.0275(4) Uani 1 1 d . . . H18 H -0.0286 0.0961 0.6162 0.033 Uiso 1 1 calc R . . C19 C 0.00946(6) 0.16816(15) 0.51694(13) 0.0246(3) Uani 1 1 d . . . H19 H -0.0248 0.2061 0.4659 0.030 Uiso 1 1 calc R . . C20 C 0.06268(6) 0.17977(13) 0.50039(12) 0.0186(3) Uani 1 1 d . . . C21 C 0.06550(6) 0.23987(13) 0.40521(12) 0.0185(3) Uani 1 1 d . . . H21 H 0.0312 0.2747 0.3509 0.022 Uiso 1 1 calc R . . C22 C 0.11751(6) 0.24861(12) 0.39016(11) 0.0161(3) 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 Cl1 0.0114(9) 0.0288(10) 0.0663(10) 0.0029(7) 0.0090(7) 0.0044(7) Cl2 0.0646(7) 0.0362(5) 0.0550(6) -0.0123(5) -0.0014(5) 0.0058(5) Cl3 0.050(2) 0.078(3) 0.181(4) 0.003(2) 0.040(2) -0.0029(19) C23 0.0220(16) 0.0249(17) 0.064(2) -0.0055(15) 0.0022(16) 0.0005(12) O1 0.0185(5) 0.0270(6) 0.0209(5) 0.0047(4) 0.0070(4) 0.0061(4) C1 0.0143(6) 0.0185(6) 0.0160(6) -0.0011(5) 0.0051(5) -0.0011(5) C2 0.0142(6) 0.0161(6) 0.0164(6) 0.0004(5) 0.0053(5) -0.0007(5) C3 0.0145(6) 0.0186(6) 0.0162(6) 0.0010(5) 0.0047(5) -0.0019(5) C4 0.0176(6) 0.0170(6) 0.0163(6) -0.0006(5) 0.0074(5) -0.0034(5) C5 0.0206(7) 0.0221(7) 0.0157(6) -0.0014(5) 0.0061(5) -0.0043(5) C6 0.0269(7) 0.0231(7) 0.0189(6) -0.0053(5) 0.0121(6) -0.0063(6) C7 0.0228(7) 0.0212(7) 0.0251(7) -0.0059(5) 0.0138(6) -0.0036(5) C8 0.0178(6) 0.0190(7) 0.0219(7) -0.0018(5) 0.0089(5) -0.0013(5) C9 0.0166(6) 0.0156(6) 0.0184(6) -0.0014(5) 0.0079(5) -0.0034(5) C10 0.0134(6) 0.0168(6) 0.0163(6) -0.0004(5) 0.0047(5) -0.0013(5) C11 0.0138(6) 0.0161(6) 0.0149(6) -0.0005(4) 0.0049(5) -0.0020(5) C12 0.0137(6) 0.0154(6) 0.0154(6) 0.0008(5) 0.0057(5) 0.0017(5) C13 0.0132(6) 0.0166(6) 0.0158(6) -0.0027(5) 0.0055(5) -0.0006(5) C14 0.0145(6) 0.0174(6) 0.0164(6) -0.0014(5) 0.0052(5) 0.0000(5) C15 0.0169(6) 0.0173(6) 0.0177(6) -0.0021(5) 0.0082(5) -0.0010(5) C16 0.0220(7) 0.0196(7) 0.0190(6) -0.0007(5) 0.0093(5) 0.0003(5) C17 0.0287(8) 0.0255(7) 0.0247(7) 0.0016(6) 0.0164(6) -0.0007(6) C18 0.0211(7) 0.0360(9) 0.0321(8) 0.0029(6) 0.0175(6) 0.0013(6) C19 0.0169(7) 0.0325(8) 0.0265(7) 0.0021(6) 0.0106(6) 0.0030(6) C20 0.0157(6) 0.0215(7) 0.0201(6) -0.0011(5) 0.0083(5) 0.0004(5) C21 0.0144(6) 0.0213(7) 0.0191(6) 0.0005(5) 0.0058(5) 0.0020(5) C22 0.0148(6) 0.0166(6) 0.0166(6) -0.0008(5) 0.0056(5) 0.0002(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C23 1.683(5) . ? Cl2 C23 1.764(5) . ? Cl3 C23 1.868(6) . ? C23 H22 1.0000 . ? O1 C1 1.2193(17) . ? C1 C22 1.4926(18) . ? C1 C2 1.4931(17) . ? C2 C3 1.3797(18) . ? C2 C11 1.4323(18) . ? C3 C4 1.4148(18) . ? C3 H3 0.9500 . ? C4 C5 1.4232(18) . ? C4 C9 1.4272(19) . ? C5 C6 1.369(2) . ? C5 H5 0.9500 . ? C6 C7 1.416(2) . ? C6 H6 0.9500 . ? C7 C8 1.3714(19) . ? C7 H7 0.9500 . ? C8 C9 1.4222(18) . ? C8 H8 0.9500 . ? C9 C10 1.4159(18) . ? C10 C11 1.3774(18) . ? C10 H10 0.9500 . ? C11 C12 1.4869(17) . ? C12 C12 1.357(3) 7_556 ? C12 C13 1.4901(17) . ? C13 C14 1.3736(18) . ? C13 C22 1.4307(18) . ? C14 C15 1.4208(18) . ? C14 H14 0.9500 . ? C15 C16 1.4223(19) . ? C15 C20 1.4257(19) . ? C16 C17 1.373(2) . ? C16 H16 0.9500 . ? C17 C18 1.412(2) . ? C17 H17 0.9500 . ? C18 C19 1.366(2) . ? C18 H18 0.9500 . ? C19 C20 1.4223(18) . ? C19 H19 0.9500 . ? C20 C21 1.4113(19) . ? C21 C22 1.3804(18) . ? C21 H21 0.9500 . ? 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 Cl1 C23 Cl2 112.9(2) . . ? Cl1 C23 Cl3 107.8(2) . . ? Cl2 C23 Cl3 112.8(3) . . ? Cl1 C23 H22 107.7 . . ? Cl2 C23 H22 107.7 . . ? Cl3 C23 H22 107.7 . . ? O1 C1 C22 122.63(12) . . ? O1 C1 C2 122.42(12) . . ? C22 C1 C2 114.49(11) . . ? C3 C2 C11 120.57(12) . . ? C3 C2 C1 119.53(12) . . ? C11 C2 C1 119.57(11) . . ? C2 C3 C4 121.04(12) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 122.68(12) . . ? C3 C4 C9 118.46(12) . . ? C5 C4 C9 118.84(12) . . ? C6 C5 C4 120.43(13) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.69(13) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.45(13) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.28(13) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 121.16(13) . . ? C10 C9 C4 119.55(12) . . ? C8 C9 C4 119.29(12) . . ? C11 C10 C9 121.43(12) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C2 118.86(12) . . ? C10 C11 C12 123.47(12) . . ? C2 C11 C12 117.63(11) . . ? C12 C12 C11 124.18(15) 7_556 . ? C12 C12 C13 123.81(15) 7_556 . ? C11 C12 C13 111.93(11) . . ? C14 C13 C22 119.32(12) . . ? C14 C13 C12 123.88(12) . . ? C22 C13 C12 116.79(11) . . ? C13 C14 C15 121.06(12) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C16 122.03(13) . . ? C14 C15 C20 119.12(12) . . ? C16 C15 C20 118.84(12) . . ? C17 C16 C15 120.30(13) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.71(13) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 120.41(13) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 120.52(14) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 121.77(13) . . ? C21 C20 C15 119.02(12) . . ? C19 C20 C15 119.17(13) . . ? C22 C21 C20 120.72(12) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C13 120.28(12) . . ? C21 C22 C1 119.39(12) . . ? C13 C22 C1 120.01(11) . . ? 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 O1 C1 C2 C3 -22.9(2) . . . . ? C22 C1 C2 C3 149.55(12) . . . . ? O1 C1 C2 C11 163.70(13) . . . . ? C22 C1 C2 C11 -23.89(17) . . . . ? C11 C2 C3 C4 3.4(2) . . . . ? C1 C2 C3 C4 -169.95(12) . . . . ? C2 C3 C4 C5 177.46(13) . . . . ? C2 C3 C4 C9 -1.4(2) . . . . ? C3 C4 C5 C6 179.63(13) . . . . ? C9 C4 C5 C6 -1.5(2) . . . . ? C4 C5 C6 C7 0.7(2) . . . . ? C5 C6 C7 C8 0.7(2) . . . . ? C6 C7 C8 C9 -1.2(2) . . . . ? C7 C8 C9 C10 -179.24(12) . . . . ? C7 C8 C9 C4 0.4(2) . . . . ? C3 C4 C9 C10 -0.49(19) . . . . ? C5 C4 C9 C10 -179.42(12) . . . . ? C3 C4 C9 C8 179.87(12) . . . . ? C5 C4 C9 C8 0.95(19) . . . . ? C8 C9 C10 C11 -179.98(12) . . . . ? C4 C9 C10 C11 0.4(2) . . . . ? C9 C10 C11 C2 1.5(2) . . . . ? C9 C10 C11 C12 179.26(12) . . . . ? C3 C2 C11 C10 -3.47(19) . . . . ? C1 C2 C11 C10 169.90(12) . . . . ? C3 C2 C11 C12 178.69(12) . . . . ? C1 C2 C11 C12 -7.94(18) . . . . ? C10 C11 C12 C12 47.1(2) . . . 7_556 ? C2 C11 C12 C12 -135.15(17) . . . 7_556 ? C10 C11 C12 C13 -135.95(13) . . . . ? C2 C11 C12 C13 41.79(16) . . . . ? C12 C12 C13 C14 -48.4(2) 7_556 . . . ? C11 C12 C13 C14 134.68(13) . . . . ? C12 C12 C13 C22 132.73(17) 7_556 . . . ? C11 C12 C13 C22 -44.23(16) . . . . ? C22 C13 C14 C15 -4.0(2) . . . . ? C12 C13 C14 C15 177.12(12) . . . . ? C13 C14 C15 C16 177.84(12) . . . . ? C13 C14 C15 C20 -2.2(2) . . . . ? C14 C15 C16 C17 178.67(13) . . . . ? C20 C15 C16 C17 -1.3(2) . . . . ? C15 C16 C17 C18 -0.8(2) . . . . ? C16 C17 C18 C19 1.6(2) . . . . ? C17 C18 C19 C20 -0.3(3) . . . . ? C18 C19 C20 C21 175.68(15) . . . . ? C18 C19 C20 C15 -1.8(2) . . . . ? C14 C15 C20 C21 5.0(2) . . . . ? C16 C15 C20 C21 -175.00(13) . . . . ? C14 C15 C20 C19 -177.39(13) . . . . ? C16 C15 C20 C19 2.6(2) . . . . ? C19 C20 C21 C22 -179.11(14) . . . . ? C15 C20 C21 C22 -1.6(2) . . . . ? C20 C21 C22 C13 -4.6(2) . . . . ? C20 C21 C22 C1 168.91(13) . . . . ? C14 C13 C22 C21 7.5(2) . . . . ? C12 C13 C22 C21 -173.54(12) . . . . ? C14 C13 C22 C1 -166.02(12) . . . . ? C12 C13 C22 C1 12.94(18) . . . . ? O1 C1 C22 C21 20.1(2) . . . . ? C2 C1 C22 C21 -152.27(13) . . . . ? O1 C1 C22 C13 -166.30(13) . . . . ? C2 C1 C22 C13 21.30(17) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.874 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.141 _database_code_depnum_ccdc_archive 'CCDC 923850' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl3 #TrackingRef '2PQ_P.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H24 O2, C H Cl3' _chemical_formula_sum 'C45 H25 Cl3 O2' _chemical_formula_weight 704.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _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 11.4108(3) _cell_length_b 11.8461(3) _cell_length_c 13.6538(3) _cell_angle_alpha 83.8430(10) _cell_angle_beta 66.3800(10) _cell_angle_gamma 84.2300(10) _cell_volume 1677.90(7) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 12896 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.49 _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9399 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16886 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7660 _reflns_number_gt 5983 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0822P)^2^+0.2873P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7660 _refine_ls_number_parameters 483 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1352 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.39938(13) 0.67293(15) 0.18415(9) 0.0555(4) Uani 0.552(4) 1 d P A 1 Cl2 Cl 0.31623(19) 0.45711(16) 0.1795(3) 0.0830(8) Uani 0.552(4) 1 d P A 1 Cl3 Cl 0.3426(2) 0.6283(2) 0.00719(10) 0.0809(8) Uani 0.552(4) 1 d P A 1 Cl4 Cl 0.2921(2) 0.5531(3) 0.02128(11) 0.0735(8) Uani 0.448(4) 1 d P A 2 Cl5 Cl 0.39617(18) 0.69551(19) 0.1207(5) 0.1311(19) Uani 0.448(4) 1 d P A 2 Cl6 Cl 0.3125(3) 0.4758(2) 0.21799(16) 0.0721(7) Uani 0.448(4) 1 d P A 2 O1 O -0.13422(10) 0.13678(9) 0.06480(8) 0.0306(3) Uani 1 1 d . . . O2 O -0.02694(10) 0.29649(9) 0.70310(8) 0.0268(2) Uani 1 1 d . . . C1 C -0.07097(13) 0.21774(12) 0.05491(11) 0.0218(3) Uani 1 1 d . . . C2 C 0.04042(13) 0.24827(12) -0.04523(10) 0.0211(3) Uani 1 1 d . . . C3 C 0.10365(14) 0.16518(13) -0.11457(11) 0.0237(3) Uani 1 1 d . . . H3 H 0.0689 0.0930 -0.1028 0.028 Uiso 1 1 calc R . . C4 C 0.21964(14) 0.18625(13) -0.20305(11) 0.0243(3) Uani 1 1 d . . . C5 C 0.28903(15) 0.10120(14) -0.27412(12) 0.0303(3) Uani 1 1 d . . . H5 H 0.2558 0.0285 -0.2642 0.036 Uiso 1 1 calc R . . C6 C 0.40360(16) 0.12345(15) -0.35687(12) 0.0344(4) Uani 1 1 d . . . H6 H 0.4491 0.0663 -0.4044 0.041 Uiso 1 1 calc R . . C7 C 0.45422(15) 0.23041(15) -0.37181(12) 0.0340(4) Uani 1 1 d . . . H7 H 0.5338 0.2448 -0.4294 0.041 Uiso 1 1 calc R . . C8 C 0.39044(14) 0.31380(14) -0.30459(12) 0.0298(3) Uani 1 1 d . . . H8 H 0.4262 0.3854 -0.3157 0.036 Uiso 1 1 calc R . . C9 C 0.27103(13) 0.29445(12) -0.21822(11) 0.0236(3) Uani 1 1 d . . . C10 C 0.20317(13) 0.37901(12) -0.14638(10) 0.0222(3) Uani 1 1 d . . . H10 H 0.2378 0.4511 -0.1565 0.027 Uiso 1 1 calc R . . C11 C 0.08836(13) 0.35876(11) -0.06249(10) 0.0201(3) Uani 1 1 d . . . C12 C 0.01227(13) 0.44502(11) 0.01474(10) 0.0200(3) Uani 1 1 d . . . C13 C -0.03833(12) 0.39436(11) 0.12745(10) 0.0193(3) Uani 1 1 d . . . C14 C -0.03545(13) 0.44473(11) 0.21283(10) 0.0201(3) Uani 1 1 d . . . H14 H 0.0027 0.5153 0.2006 0.024 Uiso 1 1 calc R . . C15 C -0.08849(12) 0.39301(11) 0.31870(10) 0.0194(3) Uani 1 1 d . . . C16 C -0.08361(14) 0.44287(12) 0.40699(11) 0.0240(3) Uani 1 1 d . . . H16 H -0.0428 0.5120 0.3956 0.029 Uiso 1 1 calc R . . C17 C -0.13747(15) 0.39172(14) 0.50859(11) 0.0284(3) Uani 1 1 d . . . H17 H -0.1349 0.4265 0.5672 0.034 Uiso 1 1 calc R . . C18 C -0.19666(14) 0.28817(13) 0.52725(11) 0.0274(3) Uani 1 1 d . . . H18 H -0.2334 0.2537 0.5981 0.033 Uiso 1 1 calc R . . C19 C -0.20133(13) 0.23725(12) 0.44376(11) 0.0241(3) Uani 1 1 d . . . H19 H -0.2406 0.1671 0.4569 0.029 Uiso 1 1 calc R . . C20 C -0.14788(12) 0.28833(12) 0.33747(10) 0.0202(3) Uani 1 1 d . . . C21 C -0.14537(13) 0.23571(12) 0.24876(11) 0.0209(3) Uani 1 1 d . . . H21 H -0.1825 0.1647 0.2598 0.025 Uiso 1 1 calc R . . C22 C -0.08992(12) 0.28558(12) 0.14654(10) 0.0201(3) Uani 1 1 d . . . C23 C 0.00155(13) 0.20510(12) 0.66133(11) 0.0212(3) Uani 1 1 d . . . C24 C -0.06810(13) 0.10179(12) 0.71333(11) 0.0212(3) Uani 1 1 d . . . C25 C -0.14723(14) 0.09744(13) 0.82107(11) 0.0244(3) Uani 1 1 d . . . H25 H -0.1609 0.1628 0.8599 0.029 Uiso 1 1 calc R . . C26 C -0.20817(14) -0.00278(13) 0.87435(11) 0.0253(3) Uani 1 1 d . . . C27 C -0.29881(15) -0.00736(15) 0.98236(12) 0.0308(3) Uani 1 1 d . . . H27 H -0.3203 0.0586 1.0215 0.037 Uiso 1 1 calc R . . C28 C -0.35510(15) -0.10653(15) 1.03015(12) 0.0339(4) Uani 1 1 d . . . H28 H -0.4178 -0.1084 1.1016 0.041 Uiso 1 1 calc R . . C29 C -0.32073(16) -0.20580(15) 0.97416(13) 0.0355(4) Uani 1 1 d . . . H29 H -0.3588 -0.2746 1.0090 0.043 Uiso 1 1 calc R . . C30 C -0.23355(15) -0.20457(14) 0.87071(13) 0.0311(3) Uani 1 1 d . . . H30 H -0.2106 -0.2726 0.8344 0.037 Uiso 1 1 calc R . . C31 C -0.17697(13) -0.10202(12) 0.81705(11) 0.0241(3) Uani 1 1 d . . . C32 C -0.09578(13) -0.09609(12) 0.70722(11) 0.0231(3) Uani 1 1 d . . . H32 H -0.0738 -0.1633 0.6697 0.028 Uiso 1 1 calc R . . C33 C -0.04779(13) 0.00470(12) 0.65327(11) 0.0206(3) Uani 1 1 d . . . C34 C 0.02081(13) 0.01979(11) 0.53496(10) 0.0202(3) Uani 1 1 d . . . C35 C 0.13190(13) 0.09163(12) 0.50192(10) 0.0206(3) Uani 1 1 d . . . C36 C 0.24796(13) 0.07058(12) 0.41826(11) 0.0233(3) Uani 1 1 d . . . H36 H 0.2637 0.0012 0.3847 0.028 Uiso 1 1 calc R . . C37 C 0.34428(13) 0.14995(12) 0.38125(11) 0.0236(3) Uani 1 1 d . . . C38 C 0.46013(14) 0.13325(14) 0.28941(12) 0.0282(3) Uani 1 1 d . . . H38 H 0.4748 0.0664 0.2524 0.034 Uiso 1 1 calc R . . C39 C 0.55003(15) 0.21208(15) 0.25403(12) 0.0325(4) Uani 1 1 d . . . H39 H 0.6268 0.1998 0.1927 0.039 Uiso 1 1 calc R . . C40 C 0.52976(15) 0.31211(15) 0.30813(13) 0.0345(4) Uani 1 1 d . . . H40 H 0.5932 0.3664 0.2831 0.041 Uiso 1 1 calc R . . C41 C 0.41942(15) 0.33135(14) 0.39615(12) 0.0311(3) Uani 1 1 d . . . H41 H 0.4068 0.3988 0.4319 0.037 Uiso 1 1 calc R . . C42 C 0.32372(13) 0.25122(12) 0.43434(11) 0.0244(3) Uani 1 1 d . . . C43 C 0.20887(13) 0.26733(12) 0.52568(11) 0.0240(3) Uani 1 1 d . . . H43 H 0.1958 0.3327 0.5644 0.029 Uiso 1 1 calc R . . C44 C 0.11562(13) 0.19003(12) 0.55949(11) 0.0210(3) Uani 1 1 d . . . C45 C 0.29467(18) 0.59866(16) 0.14433(15) 0.0416(4) Uani 1 1 d . . . H45 H 0.206(2) 0.6317(18) 0.1808(16) 0.046(5) 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 Cl1 0.0375(6) 0.0754(9) 0.0459(7) -0.0230(5) 0.0010(4) -0.0251(5) Cl2 0.0645(9) 0.0346(7) 0.149(2) 0.0096(11) -0.0443(13) -0.0081(6) Cl3 0.0854(11) 0.1223(18) 0.0344(6) -0.0216(7) -0.0282(6) 0.0320(12) Cl4 0.0694(11) 0.1023(18) 0.0404(7) -0.0036(7) -0.0176(6) 0.0138(11) Cl5 0.0365(8) 0.0551(11) 0.285(5) -0.039(2) -0.0376(18) -0.0079(7) Cl6 0.1055(15) 0.0664(13) 0.0434(9) -0.0172(7) -0.0340(8) 0.0339(10) O1 0.0300(6) 0.0323(6) 0.0284(6) -0.0074(4) -0.0067(4) -0.0120(5) O2 0.0281(5) 0.0230(5) 0.0264(5) -0.0069(4) -0.0058(4) -0.0047(4) C1 0.0205(7) 0.0216(7) 0.0234(7) -0.0029(5) -0.0083(5) -0.0023(5) C2 0.0205(6) 0.0230(7) 0.0198(7) -0.0017(5) -0.0079(5) -0.0012(5) C3 0.0264(7) 0.0231(7) 0.0219(7) -0.0035(5) -0.0093(5) -0.0014(6) C4 0.0250(7) 0.0266(8) 0.0210(7) -0.0043(5) -0.0093(5) 0.0037(6) C5 0.0332(8) 0.0296(8) 0.0271(8) -0.0070(6) -0.0112(6) 0.0046(6) C6 0.0333(8) 0.0393(9) 0.0257(8) -0.0110(6) -0.0081(6) 0.0132(7) C7 0.0233(7) 0.0463(10) 0.0248(8) -0.0048(6) -0.0032(6) 0.0069(7) C8 0.0237(7) 0.0343(9) 0.0255(8) 0.0008(6) -0.0047(6) 0.0003(6) C9 0.0216(7) 0.0279(8) 0.0194(7) -0.0007(5) -0.0073(5) 0.0029(6) C10 0.0226(7) 0.0210(7) 0.0204(7) 0.0006(5) -0.0066(5) -0.0006(5) C11 0.0214(7) 0.0192(7) 0.0184(6) -0.0013(5) -0.0071(5) 0.0010(5) C12 0.0186(6) 0.0208(7) 0.0180(6) -0.0016(5) -0.0041(5) -0.0029(5) C13 0.0172(6) 0.0178(7) 0.0201(7) -0.0007(5) -0.0049(5) 0.0000(5) C14 0.0200(6) 0.0163(6) 0.0228(7) -0.0007(5) -0.0073(5) -0.0022(5) C15 0.0170(6) 0.0196(7) 0.0200(7) -0.0021(5) -0.0058(5) 0.0009(5) C16 0.0243(7) 0.0229(7) 0.0253(7) -0.0039(5) -0.0094(5) -0.0029(5) C17 0.0313(8) 0.0338(8) 0.0213(7) -0.0036(6) -0.0110(6) -0.0032(6) C18 0.0265(7) 0.0331(8) 0.0193(7) 0.0027(5) -0.0062(6) -0.0036(6) C19 0.0216(7) 0.0232(7) 0.0239(7) 0.0020(5) -0.0058(5) -0.0029(5) C20 0.0163(6) 0.0205(7) 0.0216(7) -0.0005(5) -0.0054(5) -0.0008(5) C21 0.0175(6) 0.0191(7) 0.0241(7) -0.0016(5) -0.0057(5) -0.0035(5) C22 0.0180(6) 0.0205(7) 0.0211(7) -0.0019(5) -0.0071(5) -0.0007(5) C23 0.0204(6) 0.0226(7) 0.0209(7) -0.0037(5) -0.0080(5) -0.0021(5) C24 0.0200(6) 0.0234(7) 0.0210(7) -0.0016(5) -0.0081(5) -0.0035(5) C25 0.0247(7) 0.0286(8) 0.0203(7) -0.0041(5) -0.0078(5) -0.0052(6) C26 0.0220(7) 0.0333(8) 0.0215(7) 0.0001(5) -0.0090(5) -0.0055(6) C27 0.0294(8) 0.0406(9) 0.0224(7) -0.0014(6) -0.0086(6) -0.0096(7) C28 0.0300(8) 0.0474(10) 0.0222(8) 0.0061(6) -0.0084(6) -0.0110(7) C29 0.0335(9) 0.0349(9) 0.0344(9) 0.0117(7) -0.0114(7) -0.0089(7) C30 0.0311(8) 0.0251(8) 0.0334(8) 0.0065(6) -0.0109(6) -0.0023(6) C31 0.0217(7) 0.0257(7) 0.0253(7) 0.0035(5) -0.0107(6) -0.0025(6) C32 0.0213(7) 0.0218(7) 0.0258(7) -0.0018(5) -0.0091(5) 0.0000(5) C33 0.0178(6) 0.0217(7) 0.0218(7) -0.0030(5) -0.0073(5) -0.0005(5) C34 0.0191(6) 0.0167(7) 0.0221(7) -0.0036(5) -0.0053(5) 0.0008(5) C35 0.0203(6) 0.0202(7) 0.0206(7) -0.0009(5) -0.0074(5) -0.0019(5) C36 0.0218(7) 0.0229(7) 0.0243(7) -0.0046(5) -0.0078(5) 0.0001(5) C37 0.0194(7) 0.0269(8) 0.0228(7) -0.0007(5) -0.0072(5) -0.0001(5) C38 0.0220(7) 0.0306(8) 0.0284(8) -0.0049(6) -0.0063(6) 0.0008(6) C39 0.0205(7) 0.0409(9) 0.0284(8) -0.0009(6) -0.0017(6) -0.0024(6) C40 0.0256(8) 0.0350(9) 0.0375(9) 0.0022(7) -0.0060(6) -0.0108(7) C41 0.0270(8) 0.0298(8) 0.0326(8) -0.0014(6) -0.0069(6) -0.0068(6) C42 0.0218(7) 0.0251(7) 0.0253(7) -0.0004(5) -0.0083(5) -0.0032(6) C43 0.0232(7) 0.0222(7) 0.0257(7) -0.0027(5) -0.0080(6) -0.0027(5) C44 0.0204(7) 0.0212(7) 0.0207(7) -0.0019(5) -0.0074(5) -0.0013(5) C45 0.0365(10) 0.0381(10) 0.0440(10) -0.0085(7) -0.0094(8) 0.0033(8) _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 Cl1 C45 1.825(2) . ? Cl2 C45 1.715(3) . ? Cl3 C45 1.734(2) . ? Cl4 C45 1.831(3) . ? Cl5 C45 1.628(3) . ? Cl6 C45 1.721(3) . ? O1 C1 1.2215(17) . ? O2 C23 1.2313(17) . ? C1 C2 1.4865(18) . ? C1 C22 1.4906(18) . ? C2 C3 1.3768(19) . ? C2 C11 1.4291(19) . ? C3 C4 1.4120(19) . ? C3 H3 0.9500 . ? C4 C5 1.420(2) . ? C4 C9 1.424(2) . ? C5 C6 1.370(2) . ? C5 H5 0.9500 . ? C6 C7 1.406(3) . ? C6 H6 0.9500 . ? C7 C8 1.365(2) . ? C7 H7 0.9500 . ? C8 C9 1.4202(19) . ? C8 H8 0.9500 . ? C9 C10 1.4182(19) . ? C10 C11 1.3739(18) . ? C10 H10 0.9500 . ? C11 C12 1.4930(18) . ? C12 C12 1.357(3) 2_565 ? C12 C13 1.4904(18) . ? C13 C14 1.3784(19) . ? C13 C22 1.4256(19) . ? C14 C15 1.4195(18) . ? C14 H14 0.9500 . ? C15 C16 1.4206(19) . ? C15 C20 1.4229(19) . ? C16 C17 1.371(2) . ? C16 H16 0.9500 . ? C17 C18 1.410(2) . ? C17 H17 0.9500 . ? C18 C19 1.367(2) . ? C18 H18 0.9500 . ? C19 C20 1.4216(19) . ? C19 H19 0.9500 . ? C20 C21 1.4096(19) . ? C21 C22 1.3741(19) . ? C21 H21 0.9500 . ? C23 C24 1.4799(19) . ? C23 C44 1.4886(18) . ? C24 C25 1.3823(19) . ? C24 C33 1.4301(19) . ? C25 C26 1.413(2) . ? C25 H25 0.9500 . ? C26 C31 1.418(2) . ? C26 C27 1.421(2) . ? C27 C28 1.367(2) . ? C27 H27 0.9500 . ? C28 C29 1.407(3) . ? C28 H28 0.9500 . ? C29 C30 1.363(2) . ? C29 H29 0.9500 . ? C30 C31 1.420(2) . ? C30 H30 0.9500 . ? C31 C32 1.410(2) . ? C32 C33 1.374(2) . ? C32 H32 0.9500 . ? C33 C34 1.4857(18) . ? C34 C34 1.364(3) 2_556 ? C34 C35 1.4869(18) . ? C35 C36 1.3795(19) . ? C35 C44 1.4308(19) . ? C36 C37 1.417(2) . ? C36 H36 0.9500 . ? C37 C42 1.419(2) . ? C37 C38 1.4253(19) . ? C38 C39 1.362(2) . ? C38 H38 0.9500 . ? C39 C40 1.414(2) . ? C39 H39 0.9500 . ? C40 C41 1.368(2) . ? C40 H40 0.9500 . ? C41 C42 1.418(2) . ? C41 H41 0.9500 . ? C42 C43 1.4144(19) . ? C43 C44 1.3767(19) . ? C43 H43 0.9500 . ? C45 H45 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 C1 C2 122.95(12) . . ? O1 C1 C22 122.33(12) . . ? C2 C1 C22 114.35(11) . . ? C3 C2 C11 121.00(12) . . ? C3 C2 C1 118.81(13) . . ? C11 C2 C1 119.84(12) . . ? C2 C3 C4 120.65(13) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 121.95(14) . . ? C3 C4 C9 118.73(13) . . ? C5 C4 C9 119.25(13) . . ? C6 C5 C4 120.33(15) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.36(14) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.83(14) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 120.60(15) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 121.89(14) . . ? C10 C9 C4 119.47(12) . . ? C8 C9 C4 118.63(13) . . ? C11 C10 C9 121.30(13) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C2 118.75(12) . . ? C10 C11 C12 123.53(12) . . ? C2 C11 C12 117.69(11) . . ? C12 C12 C13 124.20(15) 2_565 . ? C12 C12 C11 123.97(15) 2_565 . ? C13 C12 C11 111.77(11) . . ? C14 C13 C22 118.58(12) . . ? C14 C13 C12 124.18(12) . . ? C22 C13 C12 117.22(12) . . ? C13 C14 C15 121.21(12) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C14 C15 C16 121.72(12) . . ? C14 C15 C20 119.47(12) . . ? C16 C15 C20 118.81(12) . . ? C17 C16 C15 120.33(13) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 120.85(13) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 120.21(13) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.59(13) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 122.19(13) . . ? C21 C20 C15 118.53(12) . . ? C19 C20 C15 119.18(12) . . ? C22 C21 C20 120.95(13) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C13 121.03(12) . . ? C21 C22 C1 118.36(12) . . ? C13 C22 C1 120.23(11) . . ? O2 C23 C24 122.34(12) . . ? O2 C23 C44 121.42(12) . . ? C24 C23 C44 116.04(12) . . ? C25 C24 C33 120.28(13) . . ? C25 C24 C23 119.84(12) . . ? C33 C24 C23 119.79(12) . . ? C24 C25 C26 121.00(13) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C25 C26 C31 118.24(13) . . ? C25 C26 C27 122.50(14) . . ? C31 C26 C27 119.26(14) . . ? C28 C27 C26 120.16(15) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C29 120.39(14) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C30 C29 C28 120.94(15) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? C29 C30 C31 120.23(15) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C32 C31 C26 119.75(13) . . ? C32 C31 C30 121.24(14) . . ? C26 C31 C30 118.94(13) . . ? C33 C32 C31 121.44(13) . . ? C33 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? C32 C33 C24 118.59(12) . . ? C32 C33 C34 123.59(12) . . ? C24 C33 C34 117.78(12) . . ? C34 C34 C35 124.00(15) 2_556 . ? C34 C34 C33 123.27(16) 2_556 . ? C35 C34 C33 112.49(11) . . ? C36 C35 C44 118.32(12) . . ? C36 C35 C34 124.15(12) . . ? C44 C35 C34 117.51(11) . . ? C35 C36 C37 121.56(13) . . ? C35 C36 H36 119.2 . . ? C37 C36 H36 119.2 . . ? C36 C37 C42 119.46(12) . . ? C36 C37 C38 121.93(13) . . ? C42 C37 C38 118.57(13) . . ? C39 C38 C37 120.79(14) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? C38 C39 C40 120.37(14) . . ? C38 C39 H39 119.8 . . ? C40 C39 H39 119.8 . . ? C41 C40 C39 120.47(14) . . ? C41 C40 H40 119.8 . . ? C39 C40 H40 119.8 . . ? C40 C41 C42 120.41(15) . . ? C40 C41 H41 119.8 . . ? C42 C41 H41 119.8 . . ? C43 C42 C41 122.19(13) . . ? C43 C42 C37 118.43(13) . . ? C41 C42 C37 119.37(13) . . ? C44 C43 C42 121.19(13) . . ? C44 C43 H43 119.4 . . ? C42 C43 H43 119.4 . . ? C43 C44 C35 120.62(12) . . ? C43 C44 C23 119.30(12) . . ? C35 C44 C23 119.92(12) . . ? Cl5 C45 Cl2 126.31(18) . . ? Cl5 C45 Cl6 117.4(2) . . ? Cl2 C45 Cl6 19.35(11) . . ? Cl5 C45 Cl3 78.5(2) . . ? Cl2 C45 Cl3 112.98(14) . . ? Cl6 C45 Cl3 131.03(14) . . ? Cl5 C45 Cl1 29.3(2) . . ? Cl2 C45 Cl1 106.13(14) . . ? Cl6 C45 Cl1 92.02(14) . . ? Cl3 C45 Cl1 106.50(13) . . ? Cl5 C45 Cl4 112.5(2) . . ? Cl2 C45 Cl4 86.59(13) . . ? Cl6 C45 Cl4 105.89(13) . . ? Cl3 C45 Cl4 34.73(7) . . ? Cl1 C45 Cl4 138.21(14) . . ? Cl5 C45 H45 109.7(12) . . ? Cl2 C45 H45 114.3(12) . . ? Cl6 C45 H45 107.8(12) . . ? Cl3 C45 H45 108.8(12) . . ? Cl1 C45 H45 107.6(12) . . ? Cl4 C45 H45 102.4(12) . . ? 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 O1 C1 C2 C3 -23.5(2) . . . . ? C22 C1 C2 C3 149.68(13) . . . . ? O1 C1 C2 C11 163.15(14) . . . . ? C22 C1 C2 C11 -23.67(18) . . . . ? C11 C2 C3 C4 1.8(2) . . . . ? C1 C2 C3 C4 -171.52(13) . . . . ? C2 C3 C4 C5 178.09(14) . . . . ? C2 C3 C4 C9 1.0(2) . . . . ? C3 C4 C5 C6 -177.63(14) . . . . ? C9 C4 C5 C6 -0.5(2) . . . . ? C4 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C8 -0.1(2) . . . . ? C6 C7 C8 C9 -0.3(2) . . . . ? C7 C8 C9 C10 179.33(14) . . . . ? C7 C8 C9 C4 0.2(2) . . . . ? C3 C4 C9 C10 -1.8(2) . . . . ? C5 C4 C9 C10 -178.93(13) . . . . ? C3 C4 C9 C8 177.34(14) . . . . ? C5 C4 C9 C8 0.2(2) . . . . ? C8 C9 C10 C11 -179.32(14) . . . . ? C4 C9 C10 C11 -0.2(2) . . . . ? C9 C10 C11 C2 2.9(2) . . . . ? C9 C10 C11 C12 -179.31(12) . . . . ? C3 C2 C11 C10 -3.7(2) . . . . ? C1 C2 C11 C10 169.47(13) . . . . ? C3 C2 C11 C12 178.38(13) . . . . ? C1 C2 C11 C12 -8.42(19) . . . . ? C10 C11 C12 C12 46.1(2) . . . 2_565 ? C2 C11 C12 C12 -136.12(18) . . . 2_565 ? C10 C11 C12 C13 -136.53(14) . . . . ? C2 C11 C12 C13 41.24(17) . . . . ? C12 C12 C13 C14 -46.7(2) 2_565 . . . ? C11 C12 C13 C14 135.96(14) . . . . ? C12 C12 C13 C22 134.88(18) 2_565 . . . ? C11 C12 C13 C22 -42.48(16) . . . . ? C22 C13 C14 C15 -3.3(2) . . . . ? C12 C13 C14 C15 178.33(12) . . . . ? C13 C14 C15 C16 178.61(13) . . . . ? C13 C14 C15 C20 -1.2(2) . . . . ? C14 C15 C16 C17 178.99(14) . . . . ? C20 C15 C16 C17 -1.2(2) . . . . ? C15 C16 C17 C18 1.0(2) . . . . ? C16 C17 C18 C19 -0.1(2) . . . . ? C17 C18 C19 C20 -0.6(2) . . . . ? C18 C19 C20 C21 176.87(14) . . . . ? C18 C19 C20 C15 0.4(2) . . . . ? C14 C15 C20 C21 3.71(19) . . . . ? C16 C15 C20 C21 -176.10(13) . . . . ? C14 C15 C20 C19 -179.72(12) . . . . ? C16 C15 C20 C19 0.48(19) . . . . ? C19 C20 C21 C22 -178.19(13) . . . . ? C15 C20 C21 C22 -1.7(2) . . . . ? C20 C21 C22 C13 -2.8(2) . . . . ? C20 C21 C22 C1 170.10(12) . . . . ? C14 C13 C22 C21 5.3(2) . . . . ? C12 C13 C22 C21 -176.16(12) . . . . ? C14 C13 C22 C1 -167.47(12) . . . . ? C12 C13 C22 C1 11.06(18) . . . . ? O1 C1 C22 C21 22.6(2) . . . . ? C2 C1 C22 C21 -150.59(13) . . . . ? O1 C1 C22 C13 -164.39(13) . . . . ? C2 C1 C22 C13 22.38(18) . . . . ? O2 C23 C24 C25 -15.4(2) . . . . ? C44 C23 C24 C25 159.59(13) . . . . ? O2 C23 C24 C33 168.03(13) . . . . ? C44 C23 C24 C33 -17.02(19) . . . . ? C33 C24 C25 C26 0.8(2) . . . . ? C23 C24 C25 C26 -175.77(13) . . . . ? C24 C25 C26 C31 5.7(2) . . . . ? C24 C25 C26 C27 -174.29(14) . . . . ? C25 C26 C27 C28 179.95(15) . . . . ? C31 C26 C27 C28 0.0(2) . . . . ? C26 C27 C28 C29 2.1(2) . . . . ? C27 C28 C29 C30 -1.7(3) . . . . ? C28 C29 C30 C31 -0.8(3) . . . . ? C25 C26 C31 C32 -5.5(2) . . . . ? C27 C26 C31 C32 174.50(13) . . . . ? C25 C26 C31 C30 177.55(14) . . . . ? C27 C26 C31 C30 -2.5(2) . . . . ? C29 C30 C31 C32 -174.02(14) . . . . ? C29 C30 C31 C26 2.9(2) . . . . ? C26 C31 C32 C33 -1.4(2) . . . . ? C30 C31 C32 C33 175.54(14) . . . . ? C31 C32 C33 C24 7.9(2) . . . . ? C31 C32 C33 C34 -170.06(13) . . . . ? C25 C24 C33 C32 -7.6(2) . . . . ? C23 C24 C33 C32 168.95(13) . . . . ? C25 C24 C33 C34 170.42(13) . . . . ? C23 C24 C33 C34 -12.99(19) . . . . ? C32 C33 C34 C34 45.0(2) . . . 2_556 ? C24 C33 C34 C34 -132.96(17) . . . 2_556 ? C32 C33 C34 C35 -140.38(14) . . . . ? C24 C33 C34 C35 41.66(17) . . . . ? C34 C34 C35 C36 -45.0(2) 2_556 . . . ? C33 C34 C35 C36 140.39(14) . . . . ? C34 C34 C35 C44 133.55(18) 2_556 . . . ? C33 C34 C35 C44 -41.03(17) . . . . ? C44 C35 C36 C37 -7.2(2) . . . . ? C34 C35 C36 C37 171.41(13) . . . . ? C35 C36 C37 C42 2.9(2) . . . . ? C35 C36 C37 C38 -174.75(14) . . . . ? C36 C37 C38 C39 178.53(14) . . . . ? C42 C37 C38 C39 0.8(2) . . . . ? C37 C38 C39 C40 0.0(2) . . . . ? C38 C39 C40 C41 -0.4(3) . . . . ? C39 C40 C41 C42 -0.1(3) . . . . ? C40 C41 C42 C43 179.35(15) . . . . ? C40 C41 C42 C37 0.9(2) . . . . ? C36 C37 C42 C43 2.5(2) . . . . ? C38 C37 C42 C43 -179.78(13) . . . . ? C36 C37 C42 C41 -179.04(13) . . . . ? C38 C37 C42 C41 -1.3(2) . . . . ? C41 C42 C43 C44 178.08(14) . . . . ? C37 C42 C43 C44 -3.5(2) . . . . ? C42 C43 C44 C35 -0.8(2) . . . . ? C42 C43 C44 C23 174.67(13) . . . . ? C36 C35 C44 C43 6.1(2) . . . . ? C34 C35 C44 C43 -172.54(13) . . . . ? C36 C35 C44 C23 -169.34(12) . . . . ? C34 C35 C44 C23 11.99(19) . . . . ? O2 C23 C44 C43 17.0(2) . . . . ? C24 C23 C44 C43 -158.00(13) . . . . ? O2 C23 C44 C35 -167.47(13) . . . . ? C24 C23 C44 C35 17.53(19) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.553 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.111 _database_code_depnum_ccdc_archive 'CCDC 923851' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl4 #TrackingRef '7BPQ.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H40 O2' _chemical_formula_sum 'C52 H40 O2' _chemical_formula_weight 696.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 10.2853(3) _cell_length_b 12.1795(4) _cell_length_c 14.7576(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.4150(10) _cell_angle_gamma 90.00 _cell_volume 1773.34(10) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 10511 _cell_measurement_theta_min 3.29 _cell_measurement_theta_max 25.36 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9877 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14260 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3241 _reflns_number_gt 2867 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1093P)^2^+1.4566P] 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 3241 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.1868 _refine_ls_wR_factor_gt 0.1822 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.25851(17) 0.18554(13) 0.02544(10) 0.0336(4) Uani 1 1 d . . . C1 C 0.2183(2) 0.27960(17) 0.03029(14) 0.0244(5) Uani 1 1 d . . . C2 C 0.1774(2) 0.31897(17) 0.11315(13) 0.0229(4) Uani 1 1 d . . . C3 C 0.2218(2) 0.26008(17) 0.19818(14) 0.0256(5) Uani 1 1 d . . . H3 H 0.2589 0.1886 0.1987 0.031 Uiso 1 1 calc R . . C4 C 0.2112(2) 0.30653(18) 0.28069(14) 0.0261(5) Uani 1 1 d . . . C5 C 0.2689(2) 0.2613(2) 0.37991(15) 0.0335(5) Uani 1 1 d . . . H5 H 0.3035 0.1846 0.3799 0.040 Uiso 1 1 calc R . . C6 C 0.1619(2) 0.2710(2) 0.43295(15) 0.0336(5) Uani 1 1 d . . . H6 H 0.1348 0.2110 0.4645 0.040 Uiso 1 1 calc R . . C7 C 0.1091(2) 0.3730(2) 0.43092(15) 0.0315(5) Uani 1 1 d . . . H7 H 0.0405 0.3909 0.4601 0.038 Uiso 1 1 calc R . . C8 C 0.1701(2) 0.45669(18) 0.37723(14) 0.0267(5) Uani 1 1 d . . . H8 H 0.1287 0.5312 0.3759 0.032 Uiso 1 1 calc R . . C9 C 0.15655(19) 0.41287(17) 0.28017(13) 0.0214(4) Uani 1 1 d . . . C10 C 0.10516(19) 0.46865(17) 0.19479(13) 0.0220(4) Uani 1 1 d . . . H10 H 0.0647 0.5388 0.1942 0.026 Uiso 1 1 calc R . . C11 C 0.11322(19) 0.42125(17) 0.10984(13) 0.0212(4) Uani 1 1 d . . . C12 C 0.0621(2) 0.47561(16) 0.01564(13) 0.0209(4) Uani 1 1 d . . . C13 C 0.15831(19) 0.46512(16) -0.04277(13) 0.0216(4) Uani 1 1 d . . . C14 C 0.1846(2) 0.54966(17) -0.09957(14) 0.0237(5) Uani 1 1 d . . . H14 H 0.1434 0.6195 -0.1000 0.028 Uiso 1 1 calc R . . C15 C 0.2709(2) 0.53124(18) -0.15515(14) 0.0264(5) Uani 1 1 d . . . C16 C 0.3071(2) 0.6126(2) -0.22140(17) 0.0348(5) Uani 1 1 d . . . H16 H 0.2583 0.6841 -0.2241 0.042 Uiso 1 1 calc R . . C17 C 0.2767(3) 0.5564(3) -0.31805(18) 0.0480(7) Uani 1 1 d . . . H17 H 0.2190 0.5873 -0.3742 0.058 Uiso 1 1 calc R . . C18 C 0.3413(3) 0.4563(3) -0.31566(17) 0.0471(7) Uani 1 1 d . . . H18 H 0.3329 0.4118 -0.3699 0.056 Uiso 1 1 calc R . . C19 C 0.4269(2) 0.4253(2) -0.21757(16) 0.0348(6) Uani 1 1 d . . . H19 H 0.4712 0.3520 -0.2163 0.042 Uiso 1 1 calc R . . C20 C 0.3350(2) 0.42936(19) -0.15361(14) 0.0274(5) Uani 1 1 d . . . C21 C 0.3143(2) 0.34702(18) -0.09548(14) 0.0259(5) Uani 1 1 d . . . H21 H 0.3592 0.2785 -0.0933 0.031 Uiso 1 1 calc R . . C22 C 0.2267(2) 0.36480(17) -0.03954(13) 0.0232(5) Uani 1 1 d . . . C23 C 0.5309(3) 0.5183(2) -0.1850(2) 0.0473(7) Uani 1 1 d . . . H23A H 0.5872 0.5034 -0.1197 0.057 Uiso 1 1 calc R . . H23B H 0.5916 0.5208 -0.2264 0.057 Uiso 1 1 calc R . . C24 C 0.4622(3) 0.6259(2) -0.1879(2) 0.0483(7) Uani 1 1 d . . . H24A H 0.4914 0.6759 -0.2314 0.058 Uiso 1 1 calc R . . H24B H 0.4890 0.6593 -0.1242 0.058 Uiso 1 1 calc R . . C25 C 0.3833(2) 0.3440(2) 0.43022(15) 0.0357(6) Uani 1 1 d . . . H25A H 0.4228 0.3217 0.4969 0.043 Uiso 1 1 calc R . . H25B H 0.4563 0.3430 0.3986 0.043 Uiso 1 1 calc R . . C26 C 0.3261(2) 0.4572(2) 0.42646(15) 0.0320(5) Uani 1 1 d . . . H26A H 0.3716 0.5060 0.3912 0.038 Uiso 1 1 calc R . . H26B H 0.3437 0.4865 0.4914 0.038 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 O1 0.0467(10) 0.0308(9) 0.0253(8) 0.0007(6) 0.0132(7) 0.0085(7) C1 0.0239(10) 0.0290(11) 0.0186(10) -0.0011(8) 0.0035(8) 0.0009(8) C2 0.0215(10) 0.0289(10) 0.0179(10) -0.0002(8) 0.0048(8) -0.0022(8) C3 0.0261(10) 0.0282(10) 0.0232(10) 0.0027(8) 0.0080(8) 0.0023(8) C4 0.0252(10) 0.0334(11) 0.0195(10) 0.0047(8) 0.0062(8) 0.0017(8) C5 0.0398(13) 0.0424(13) 0.0189(11) 0.0066(9) 0.0093(9) 0.0122(10) C6 0.0345(12) 0.0443(13) 0.0222(11) 0.0092(9) 0.0083(9) -0.0042(10) C7 0.0274(11) 0.0471(13) 0.0213(11) -0.0021(9) 0.0091(9) -0.0046(9) C8 0.0255(11) 0.0369(12) 0.0180(10) -0.0002(8) 0.0069(8) 0.0019(9) C9 0.0167(9) 0.0323(11) 0.0151(9) 0.0009(8) 0.0043(7) -0.0018(8) C10 0.0178(9) 0.0300(10) 0.0181(10) 0.0005(8) 0.0050(7) 0.0000(8) C11 0.0171(9) 0.0297(10) 0.0168(10) 0.0009(8) 0.0045(7) -0.0015(8) C12 0.0223(9) 0.0249(10) 0.0154(9) -0.0007(7) 0.0053(7) -0.0020(7) C13 0.0179(9) 0.0314(11) 0.0142(9) -0.0010(8) 0.0026(7) -0.0005(8) C14 0.0196(10) 0.0315(11) 0.0189(10) 0.0008(8) 0.0036(7) 0.0002(8) C15 0.0214(10) 0.0374(12) 0.0199(10) 0.0027(8) 0.0052(8) -0.0014(8) C16 0.0323(12) 0.0449(13) 0.0321(12) 0.0108(10) 0.0171(10) 0.0029(10) C17 0.0565(16) 0.0662(18) 0.0237(12) 0.0147(12) 0.0151(11) 0.0121(14) C18 0.0516(16) 0.0724(19) 0.0225(12) 0.0020(12) 0.0190(11) 0.0082(14) C19 0.0302(12) 0.0509(14) 0.0273(11) 0.0041(10) 0.0146(9) 0.0064(10) C20 0.0215(10) 0.0424(12) 0.0180(10) 0.0000(9) 0.0049(8) 0.0018(9) C21 0.0236(10) 0.0339(11) 0.0198(10) -0.0019(8) 0.0054(8) 0.0036(8) C22 0.0220(10) 0.0314(11) 0.0155(9) -0.0018(8) 0.0041(8) -0.0010(8) C23 0.0303(13) 0.0658(18) 0.0529(16) 0.0028(13) 0.0234(12) -0.0037(12) C24 0.0356(14) 0.0550(16) 0.0598(18) 0.0117(13) 0.0226(13) -0.0076(12) C25 0.0245(11) 0.0640(16) 0.0169(10) 0.0070(10) 0.0032(8) 0.0063(10) C26 0.0259(11) 0.0463(13) 0.0217(11) -0.0009(9) 0.0032(8) -0.0047(9) _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 O1 C1 1.227(3) . ? C1 C2 1.481(3) . ? C1 C22 1.482(3) . ? C2 C11 1.404(3) . ? C2 C3 1.405(3) . ? C3 C4 1.375(3) . ? C3 H3 0.9500 . ? C4 C9 1.411(3) . ? C4 C5 1.519(3) . ? C5 C6 1.525(3) . ? C5 C25 1.568(4) . ? C5 H5 1.0000 . ? C6 C7 1.352(3) . ? C6 H6 0.9500 . ? C7 C8 1.531(3) . ? C7 H7 0.9500 . ? C8 C9 1.498(3) . ? C8 C26 1.564(3) . ? C8 H8 1.0000 . ? C9 C10 1.397(3) . ? C10 C11 1.404(3) . ? C10 H10 0.9500 . ? C11 C12 1.495(3) . ? C12 C12 1.365(4) 3_565 ? C12 C13 1.490(3) . ? C13 C14 1.402(3) . ? C13 C22 1.404(3) . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 C20 1.402(3) . ? C15 C16 1.511(3) . ? C16 C17 1.532(4) . ? C16 C24 1.540(3) . ? C16 H16 1.0000 . ? C17 C18 1.385(4) . ? C17 H17 0.9500 . ? C18 C19 1.514(3) . ? C18 H18 0.9500 . ? C19 C20 1.513(3) . ? C19 C23 1.538(4) . ? C19 H19 1.0000 . ? C20 C21 1.375(3) . ? C21 C22 1.401(3) . ? C21 H21 0.9500 . ? C23 C24 1.484(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.494(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? 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 C1 C2 121.98(18) . . ? O1 C1 C22 121.75(18) . . ? C2 C1 C22 115.69(17) . . ? C11 C2 C3 120.98(18) . . ? C11 C2 C1 119.93(17) . . ? C3 C2 C1 118.43(18) . . ? C4 C3 C2 119.61(19) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C9 120.27(18) . . ? C3 C4 C5 126.7(2) . . ? C9 C4 C5 112.62(18) . . ? C4 C5 C6 108.92(18) . . ? C4 C5 C25 105.07(18) . . ? C6 C5 C25 105.14(18) . . ? C4 C5 H5 112.4 . . ? C6 C5 H5 112.4 . . ? C25 C5 H5 112.4 . . ? C7 C6 C5 113.81(19) . . ? C7 C6 H6 123.1 . . ? C5 C6 H6 123.1 . . ? C6 C7 C8 113.72(19) . . ? C6 C7 H7 123.1 . . ? C8 C7 H7 123.1 . . ? C9 C8 C7 108.47(17) . . ? C9 C8 C26 104.58(17) . . ? C7 C8 C26 106.24(17) . . ? C9 C8 H8 112.4 . . ? C7 C8 H8 112.4 . . ? C26 C8 H8 112.4 . . ? C10 C9 C4 119.99(18) . . ? C10 C9 C8 126.76(19) . . ? C4 C9 C8 113.12(17) . . ? C9 C10 C11 120.17(18) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C2 118.66(17) . . ? C10 C11 C12 123.66(18) . . ? C2 C11 C12 117.63(17) . . ? C12 C12 C13 123.5(2) 3_565 . ? C12 C12 C11 123.8(2) 3_565 . ? C13 C12 C11 112.54(16) . . ? C14 C13 C22 118.68(18) . . ? C14 C13 C12 123.72(18) . . ? C22 C13 C12 117.59(17) . . ? C15 C14 C13 119.94(19) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C20 120.69(19) . . ? C14 C15 C16 126.3(2) . . ? C20 C15 C16 112.96(18) . . ? C15 C16 C17 106.7(2) . . ? C15 C16 C24 106.51(19) . . ? C17 C16 C24 105.4(2) . . ? C15 C16 H16 112.6 . . ? C17 C16 H16 112.6 . . ? C24 C16 H16 112.6 . . ? C18 C17 C16 113.5(2) . . ? C18 C17 H17 123.2 . . ? C16 C17 H17 123.2 . . ? C17 C18 C19 112.9(2) . . ? C17 C18 H18 123.6 . . ? C19 C18 H18 123.6 . . ? C20 C19 C18 106.95(18) . . ? C20 C19 C23 106.43(19) . . ? C18 C19 C23 106.3(2) . . ? C20 C19 H19 112.2 . . ? C18 C19 H19 112.2 . . ? C23 C19 H19 112.2 . . ? C21 C20 C15 120.03(19) . . ? C21 C20 C19 126.8(2) . . ? C15 C20 C19 113.09(19) . . ? C20 C21 C22 119.6(2) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C21 C22 C13 120.96(19) . . ? C21 C22 C1 118.38(18) . . ? C13 C22 C1 120.38(17) . . ? C24 C23 C19 111.0(2) . . ? C24 C23 H23A 109.4 . . ? C19 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? C19 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C16 111.0(2) . . ? C23 C24 H24A 109.4 . . ? C16 C24 H24A 109.4 . . ? C23 C24 H24B 109.4 . . ? C16 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C26 C25 C5 109.92(18) . . ? C26 C25 H25A 109.7 . . ? C5 C25 H25A 109.7 . . ? C26 C25 H25B 109.7 . . ? C5 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? C25 C26 C8 110.79(18) . . ? C25 C26 H26A 109.5 . . ? C8 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? C8 C26 H26B 109.5 . . ? H26A C26 H26B 108.1 . . ? 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 O1 C1 C2 C11 -170.49(19) . . . . ? C22 C1 C2 C11 18.1(3) . . . . ? O1 C1 C2 C3 18.7(3) . . . . ? C22 C1 C2 C3 -152.68(19) . . . . ? C11 C2 C3 C4 -4.7(3) . . . . ? C1 C2 C3 C4 165.95(19) . . . . ? C2 C3 C4 C9 -0.2(3) . . . . ? C2 C3 C4 C5 -172.1(2) . . . . ? C3 C4 C5 C6 -135.6(2) . . . . ? C9 C4 C5 C6 52.0(3) . . . . ? C3 C4 C5 C25 112.2(2) . . . . ? C9 C4 C5 C25 -60.2(2) . . . . ? C4 C5 C6 C7 -52.2(3) . . . . ? C25 C5 C6 C7 60.0(2) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? C6 C7 C8 C9 54.4(2) . . . . ? C6 C7 C8 C26 -57.5(2) . . . . ? C3 C4 C9 C10 4.0(3) . . . . ? C5 C4 C9 C10 176.91(18) . . . . ? C3 C4 C9 C8 -172.06(19) . . . . ? C5 C4 C9 C8 0.9(2) . . . . ? C7 C8 C9 C10 130.7(2) . . . . ? C26 C8 C9 C10 -116.3(2) . . . . ? C7 C8 C9 C4 -53.6(2) . . . . ? C26 C8 C9 C4 59.5(2) . . . . ? C4 C9 C10 C11 -2.9(3) . . . . ? C8 C9 C10 C11 172.61(18) . . . . ? C9 C10 C11 C2 -2.0(3) . . . . ? C9 C10 C11 C12 -179.39(17) . . . . ? C3 C2 C11 C10 5.8(3) . . . . ? C1 C2 C11 C10 -164.74(18) . . . . ? C3 C2 C11 C12 -176.61(18) . . . . ? C1 C2 C11 C12 12.8(3) . . . . ? C10 C11 C12 C12 -47.0(3) . . . 3_565 ? C2 C11 C12 C12 135.5(3) . . . 3_565 ? C10 C11 C12 C13 136.30(19) . . . . ? C2 C11 C12 C13 -41.1(2) . . . . ? C12 C12 C13 C14 42.9(3) 3_565 . . . ? C11 C12 C13 C14 -140.43(19) . . . . ? C12 C12 C13 C22 -137.7(2) 3_565 . . . ? C11 C12 C13 C22 39.0(2) . . . . ? C22 C13 C14 C15 3.6(3) . . . . ? C12 C13 C14 C15 -176.96(18) . . . . ? C13 C14 C15 C20 -1.5(3) . . . . ? C13 C14 C15 C16 178.6(2) . . . . ? C14 C15 C16 C17 -126.3(2) . . . . ? C20 C15 C16 C17 53.8(2) . . . . ? C14 C15 C16 C24 121.5(2) . . . . ? C20 C15 C16 C24 -58.4(3) . . . . ? C15 C16 C17 C18 -55.0(3) . . . . ? C24 C16 C17 C18 58.0(3) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? C17 C18 C19 C20 55.0(3) . . . . ? C17 C18 C19 C23 -58.4(3) . . . . ? C14 C15 C20 C21 -1.0(3) . . . . ? C16 C15 C20 C21 178.86(19) . . . . ? C14 C15 C20 C19 -179.06(19) . . . . ? C16 C15 C20 C19 0.8(3) . . . . ? C18 C19 C20 C21 126.3(2) . . . . ? C23 C19 C20 C21 -120.4(2) . . . . ? C18 C19 C20 C15 -55.8(3) . . . . ? C23 C19 C20 C15 57.5(2) . . . . ? C15 C20 C21 C22 1.4(3) . . . . ? C19 C20 C21 C22 179.1(2) . . . . ? C20 C21 C22 C13 0.8(3) . . . . ? C20 C21 C22 C1 -173.15(19) . . . . ? C14 C13 C22 C21 -3.2(3) . . . . ? C12 C13 C22 C21 177.27(18) . . . . ? C14 C13 C22 C1 170.55(18) . . . . ? C12 C13 C22 C1 -8.9(3) . . . . ? O1 C1 C22 C21 -17.7(3) . . . . ? C2 C1 C22 C21 153.73(18) . . . . ? O1 C1 C22 C13 168.36(19) . . . . ? C2 C1 C22 C13 -20.2(3) . . . . ? C20 C19 C23 C24 -57.0(3) . . . . ? C18 C19 C23 C24 56.7(3) . . . . ? C19 C23 C24 C16 0.8(3) . . . . ? C15 C16 C24 C23 56.2(3) . . . . ? C17 C16 C24 C23 -56.9(3) . . . . ? C4 C5 C25 C26 56.5(2) . . . . ? C6 C5 C25 C26 -58.4(2) . . . . ? C5 C25 C26 C8 2.2(2) . . . . ? C9 C8 C26 C25 -59.9(2) . . . . ? C7 C8 C26 C25 54.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.629 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 923852' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_20915kaz #TrackingRef '8aBPPh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C64 H50, 3(C H Cl3)' _chemical_formula_sum 'C67 H53 Cl9' _chemical_formula_weight 1177.14 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.018(3) _cell_length_b 10.2100(14) _cell_length_c 22.028(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.352(2) _cell_angle_gamma 90.00 _cell_volume 5401.5(13) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 2628 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 24.89 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2432 _exptl_absorpt_coefficient_mu 0.511 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9046 _exptl_absorpt_correction_T_max 0.9949 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27392 _diffrn_reflns_av_R_equivalents 0.0821 _diffrn_reflns_av_sigmaI/netI 0.1223 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 0.85 _diffrn_reflns_theta_max 26.00 _reflns_number_total 10549 _reflns_number_gt 5290 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1180P)^2^+5.7886P] 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 10549 _refine_ls_number_parameters 685 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1651 _refine_ls_R_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.2429 _refine_ls_wR_factor_gt 0.1927 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0573(2) 1.0698(6) 0.6074(2) 0.0246(13) Uani 1 1 d . . . H30 H 0.0921 1.1195 0.6144 0.029 Uiso 1 1 calc R . . H31 H 0.0336 1.1214 0.5794 0.029 Uiso 1 1 calc R . . C2 C 0.0284(2) 1.0544(6) 0.6651(3) 0.0328(15) Uani 1 1 d . . . H32 H -0.0088 1.0959 0.6624 0.039 Uiso 1 1 calc R . . H33 H 0.0498 1.0989 0.6977 0.039 Uiso 1 1 calc R . . C3 C 0.0219(2) 0.9087(6) 0.6806(2) 0.0259(14) Uani 1 1 d . . . H34 H 0.0030 0.8954 0.7205 0.031 Uiso 1 1 calc R . . C4 C -0.0106(2) 0.8485(6) 0.6284(3) 0.0283(14) Uani 1 1 d . . . H1 H -0.0452 0.8045 0.6331 0.034 Uiso 1 1 calc R . . C5 C 0.0163(2) 0.8650(6) 0.5716(2) 0.0244(13) Uani 1 1 d . . . H2 H 0.0017 0.8337 0.5341 0.029 Uiso 1 1 calc R . . C6 C 0.0714(2) 0.9387(5) 0.5776(2) 0.0196(12) Uani 1 1 d . . . H35 H 0.0902 0.9503 0.5375 0.024 Uiso 1 1 calc R . . C7 C 0.1067(2) 0.8613(5) 0.6221(2) 0.0166(12) Uani 1 1 d . . . C8 C 0.1566(2) 0.8028(5) 0.6124(2) 0.0146(11) Uani 1 1 d . . . H3 H 0.1729 0.8073 0.5732 0.017 Uiso 1 1 calc R . . C9 C 0.1854(2) 0.7336(5) 0.6606(2) 0.0132(11) Uani 1 1 d . . . C10 C 0.2361(2) 0.6688(5) 0.6510(2) 0.0129(11) Uani 1 1 d . . . C11 C 0.2622(2) 0.6024(5) 0.7007(2) 0.0128(11) Uani 1 1 d . . . C12 C 0.3134(2) 0.5321(5) 0.6932(2) 0.0129(11) Uani 1 1 d . . . H4 H 0.3295 0.5257 0.6541 0.015 Uiso 1 1 calc R . . C13 C 0.3391(2) 0.4745(5) 0.7415(2) 0.0152(11) Uani 1 1 d . . . C14 C 0.3938(2) 0.4000(5) 0.7419(2) 0.0212(13) Uani 1 1 d . . . H36 H 0.4097 0.3908 0.7003 0.025 Uiso 1 1 calc R . . C15 C 0.3838(2) 0.2655(6) 0.7726(2) 0.0218(13) Uani 1 1 d . . . H5 H 0.3920 0.1838 0.7540 0.026 Uiso 1 1 calc R . . C16 C 0.3613(2) 0.2781(6) 0.8315(3) 0.0265(14) Uani 1 1 d . . . H6 H 0.3530 0.2058 0.8570 0.032 Uiso 1 1 calc R . . C17 C 0.3519(2) 0.4208(6) 0.8494(2) 0.0209(13) Uani 1 1 d . . . H37 H 0.3356 0.4289 0.8908 0.025 Uiso 1 1 calc R . . C18 C 0.4092(2) 0.4882(6) 0.8451(2) 0.0227(13) Uani 1 1 d . . . H38 H 0.4051 0.5823 0.8549 0.027 Uiso 1 1 calc R . . H39 H 0.4348 0.4490 0.8754 0.027 Uiso 1 1 calc R . . C19 C 0.4330(2) 0.4753(6) 0.7855(2) 0.0220(13) Uani 1 1 d . . . H40 H 0.4690 0.4284 0.7886 0.026 Uiso 1 1 calc R . . H41 H 0.4404 0.5635 0.7686 0.026 Uiso 1 1 calc R . . C20 C 0.3155(2) 0.4833(5) 0.8015(2) 0.0154(11) Uani 1 1 d . . . C21 C 0.2666(2) 0.5457(5) 0.8094(2) 0.0164(12) Uani 1 1 d . . . H7 H 0.2508 0.5481 0.8489 0.020 Uiso 1 1 calc R . . C22 C 0.2376(2) 0.6082(5) 0.7606(2) 0.0152(11) Uani 1 1 d . . . C23 C 0.1876(2) 0.6766(5) 0.7690(2) 0.0135(11) Uani 1 1 d . . . C24 C 0.1602(2) 0.7340(5) 0.7195(2) 0.0142(11) Uani 1 1 d . . . C25 C 0.1064(2) 0.7916(5) 0.7269(2) 0.0173(12) Uani 1 1 d . . . H8 H 0.0891 0.7884 0.7655 0.021 Uiso 1 1 calc R . . C26 C 0.0797(2) 0.8508(5) 0.6801(2) 0.0184(12) Uani 1 1 d . . . C27 C 0.1641(2) 0.6942(5) 0.8317(2) 0.0133(11) Uani 1 1 d . . . C28 C 0.1744(2) 0.8093(6) 0.8626(2) 0.0259(14) Uani 1 1 d . . . H9 H 0.1972 0.8745 0.8447 0.031 Uiso 1 1 calc R . . C29 C 0.1518(2) 0.8312(6) 0.9196(2) 0.0249(14) Uani 1 1 d . . . H10 H 0.1599 0.9101 0.9408 0.030 Uiso 1 1 calc R . . C30 C 0.1178(2) 0.7380(5) 0.9454(2) 0.0195(12) Uani 1 1 d . . . H11 H 0.1014 0.7535 0.9839 0.023 Uiso 1 1 calc R . . C31 C 0.1075(2) 0.6226(6) 0.9151(2) 0.0251(14) Uani 1 1 d . . . H12 H 0.0847 0.5574 0.9331 0.030 Uiso 1 1 calc R . . C32 C 0.1306(2) 0.6015(5) 0.8580(2) 0.0199(12) Uani 1 1 d . . . H13 H 0.1230 0.5221 0.8371 0.024 Uiso 1 1 calc R . . C33 C 0.1678(2) 0.2421(5) 0.5365(2) 0.0229(13) Uani 1 1 d . . . H42 H 0.1471 0.2491 0.5756 0.027 Uiso 1 1 calc R . . C34 C 0.1281(2) 0.2396(6) 0.4808(3) 0.0269(14) Uani 1 1 d . . . H43 H 0.1026 0.1638 0.4843 0.032 Uiso 1 1 calc R . . H44 H 0.1052 0.3203 0.4805 0.032 Uiso 1 1 calc R . . C35 C 0.1577(3) 0.2306(6) 0.4259(3) 0.0329(15) Uani 1 1 d . . . H45 H 0.1488 0.3077 0.4004 0.039 Uiso 1 1 calc R . . H46 H 0.1453 0.1515 0.4037 0.039 Uiso 1 1 calc R . . C36 C 0.2208(2) 0.2236(5) 0.4352(2) 0.0217(13) Uani 1 1 d . . . H47 H 0.2414 0.2167 0.3960 0.026 Uiso 1 1 calc R . . C37 C 0.2311(2) 0.1058(6) 0.4769(2) 0.0251(13) Uani 1 1 d . . . H14 H 0.2540 0.0335 0.4665 0.030 Uiso 1 1 calc R . . C38 C 0.2024(3) 0.1171(6) 0.5329(3) 0.0294(14) Uani 1 1 d . . . H15 H 0.2044 0.0539 0.5645 0.035 Uiso 1 1 calc R . . C39 C 0.2067(2) 0.3552(5) 0.5270(2) 0.0183(12) Uani 1 1 d . . . C40 C 0.2152(2) 0.4573(5) 0.5651(2) 0.0154(11) Uani 1 1 d . . . H16 H 0.1954 0.4611 0.6023 0.018 Uiso 1 1 calc R . . C41 C 0.2534(2) 0.5597(5) 0.5503(2) 0.0124(11) Uani 1 1 d . . . C42 C 0.2632(2) 0.6642(5) 0.5896(2) 0.0124(11) Uani 1 1 d . . . C43 C 0.2998(2) 0.7671(5) 0.5718(2) 0.0143(11) Uani 1 1 d . . . C44 C 0.3109(2) 0.8758(5) 0.6107(2) 0.0160(12) Uani 1 1 d . . . H17 H 0.2935 0.8803 0.6493 0.019 Uiso 1 1 calc R . . C45 C 0.3463(2) 0.9736(5) 0.5933(2) 0.0164(12) Uani 1 1 d . . . C46 C 0.3624(2) 1.0953(6) 0.6281(2) 0.0226(13) Uani 1 1 d . . . H48 H 0.3436 1.0999 0.6684 0.027 Uiso 1 1 calc R . . C47 C 0.3480(3) 1.2130(6) 0.5880(3) 0.0308(15) Uani 1 1 d . . . H18 H 0.3243 1.2825 0.6003 0.037 Uiso 1 1 calc R . . C48 C 0.3742(2) 1.2066(5) 0.5306(3) 0.0252(13) Uani 1 1 d . . . H19 H 0.3699 1.2712 0.4999 0.030 Uiso 1 1 calc R . . C49 C 0.4100(2) 1.0840(5) 0.5237(2) 0.0162(11) Uani 1 1 d . . . H49 H 0.4281 1.0796 0.4830 0.019 Uiso 1 1 calc R . . C50 C 0.4529(2) 1.0865(6) 0.5755(2) 0.0228(13) Uani 1 1 d . . . H50 H 0.4761 1.0065 0.5736 0.027 Uiso 1 1 calc R . . H51 H 0.4776 1.1632 0.5705 0.027 Uiso 1 1 calc R . . C51 C 0.4261(2) 1.0935(6) 0.6345(3) 0.0254(13) Uani 1 1 d . . . H52 H 0.4386 1.1737 0.6558 0.030 Uiso 1 1 calc R . . H53 H 0.4375 1.0170 0.6592 0.030 Uiso 1 1 calc R . . C52 C 0.3729(2) 0.9674(5) 0.5351(2) 0.0171(12) Uani 1 1 d . . . C53 C 0.3633(2) 0.8649(5) 0.4975(2) 0.0135(11) Uani 1 1 d . . . H20 H 0.3811 0.8627 0.4591 0.016 Uiso 1 1 calc R . . C54 C 0.3273(2) 0.7609(5) 0.5137(2) 0.0126(11) Uani 1 1 d . . . C55 C 0.3191(2) 0.6511(5) 0.4757(2) 0.0132(11) Uani 1 1 d . . . C56 C 0.2827(2) 0.5510(5) 0.4929(2) 0.0123(11) Uani 1 1 d . . . C57 C 0.2730(2) 0.4409(5) 0.4546(2) 0.0155(11) Uani 1 1 d . . . H21 H 0.2923 0.4341 0.4172 0.019 Uiso 1 1 calc R . . C58 C 0.2364(2) 0.3449(5) 0.4708(2) 0.0180(12) Uani 1 1 d . . . C59 C 0.3499(2) 0.6425(5) 0.4168(2) 0.0153(11) Uani 1 1 d . . . C60 C 0.3259(3) 0.6852(6) 0.3638(2) 0.0268(14) Uani 1 1 d . . . H22 H 0.2895 0.7213 0.3646 0.032 Uiso 1 1 calc R . . C61 C 0.3538(3) 0.6767(6) 0.3091(3) 0.0296(15) Uani 1 1 d . . . H23 H 0.3368 0.7105 0.2733 0.035 Uiso 1 1 calc R . . C62 C 0.4050(3) 0.6209(6) 0.3057(2) 0.0257(14) Uani 1 1 d . . . H24 H 0.4238 0.6140 0.2680 0.031 Uiso 1 1 calc R . . C63 C 0.4290(3) 0.5747(9) 0.3581(3) 0.055(2) Uani 1 1 d . . . H25 H 0.4646 0.5344 0.3567 0.066 Uiso 1 1 calc R . . C64 C 0.4017(3) 0.5864(8) 0.4133(3) 0.044(2) Uani 1 1 d . . . H26 H 0.4192 0.5550 0.4492 0.053 Uiso 1 1 calc R . . C65 C 0.0440(3) 0.5162(7) 0.6355(3) 0.0426(18) Uani 1 1 d . . . H27 H 0.0503 0.6095 0.6475 0.051 Uiso 1 1 calc R . . Cl1 Cl 0.08642(8) 0.41786(19) 0.68075(8) 0.0486(5) Uani 1 1 d . . . Cl2 Cl -0.02724(9) 0.4792(2) 0.64698(11) 0.0701(7) Uani 1 1 d . . . Cl3 Cl 0.06026(10) 0.5004(2) 0.55871(9) 0.0683(7) Uani 1 1 d . . . C66 C 0.2003(3) 0.3956(8) 0.2236(3) 0.060(2) Uani 1 1 d . . . H28 H 0.1867 0.4532 0.1899 0.072 Uiso 1 1 calc R . . Cl4 Cl 0.25561(9) 0.4738(2) 0.26170(9) 0.0576(6) Uani 1 1 d . . . Cl5 Cl 0.14484(10) 0.3649(3) 0.27427(11) 0.0756(7) Uani 1 1 d . . . Cl6 Cl 0.22383(10) 0.2471(2) 0.19309(11) 0.0746(7) Uani 1 1 d . . . C67 C 0.4457(3) 0.8281(6) 0.0920(3) 0.0292(14) Uani 1 1 d . . . H29 H 0.4141 0.7717 0.0779 0.035 Uiso 1 1 calc R . . Cl7 Cl 0.45844(8) 0.79415(19) 0.16772(8) 0.0519(5) Uani 1 1 d . . . Cl8 Cl 0.42717(6) 0.99227(15) 0.08048(6) 0.0294(4) Uani 1 1 d . . . Cl9 Cl 0.50490(8) 0.7909(2) 0.04756(9) 0.0579(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.021(3) 0.030(3) 0.023(3) 0.006(3) 0.002(2) 0.003(3) C2 0.018(3) 0.035(4) 0.045(4) -0.012(3) -0.015(3) 0.008(3) C3 0.019(3) 0.038(4) 0.021(3) 0.009(3) 0.006(2) 0.012(3) C4 0.013(3) 0.028(3) 0.044(4) 0.005(3) -0.002(3) 0.000(3) C5 0.022(3) 0.028(3) 0.023(3) -0.005(3) -0.008(2) 0.003(3) C6 0.019(3) 0.027(3) 0.013(3) 0.004(2) -0.001(2) 0.008(2) C7 0.017(3) 0.021(3) 0.013(3) 0.001(2) 0.000(2) 0.002(2) C8 0.020(3) 0.015(3) 0.008(2) 0.002(2) 0.001(2) -0.001(2) C9 0.013(3) 0.015(3) 0.012(3) 0.000(2) 0.002(2) -0.006(2) C10 0.014(3) 0.015(3) 0.009(2) 0.001(2) 0.001(2) 0.001(2) C11 0.010(3) 0.017(3) 0.011(3) 0.000(2) 0.000(2) -0.001(2) C12 0.015(3) 0.015(3) 0.008(2) 0.000(2) 0.000(2) -0.001(2) C13 0.012(3) 0.020(3) 0.013(3) -0.001(2) 0.001(2) -0.002(2) C14 0.024(3) 0.027(3) 0.012(3) 0.005(2) 0.002(2) 0.007(3) C15 0.024(3) 0.021(3) 0.021(3) 0.001(2) -0.004(2) 0.008(3) C16 0.030(4) 0.025(3) 0.025(3) 0.011(3) -0.001(3) -0.001(3) C17 0.019(3) 0.035(3) 0.008(3) 0.004(2) -0.002(2) 0.005(3) C18 0.017(3) 0.033(3) 0.018(3) 0.000(3) -0.008(2) 0.009(3) C19 0.011(3) 0.028(3) 0.026(3) 0.003(3) -0.003(2) 0.004(2) C20 0.019(3) 0.019(3) 0.009(2) 0.002(2) -0.004(2) -0.001(2) C21 0.015(3) 0.025(3) 0.009(3) 0.003(2) 0.001(2) -0.002(2) C22 0.017(3) 0.018(3) 0.011(3) 0.002(2) 0.002(2) -0.002(2) C23 0.013(3) 0.015(3) 0.012(3) -0.001(2) 0.005(2) -0.006(2) C24 0.014(3) 0.019(3) 0.009(2) 0.001(2) -0.001(2) -0.002(2) C25 0.017(3) 0.023(3) 0.012(3) -0.001(2) 0.003(2) 0.003(2) C26 0.014(3) 0.023(3) 0.019(3) -0.003(2) -0.002(2) 0.003(2) C27 0.010(3) 0.025(3) 0.005(2) 0.002(2) -0.0009(19) 0.003(2) C28 0.028(3) 0.031(3) 0.019(3) -0.001(3) 0.010(2) -0.013(3) C29 0.035(4) 0.021(3) 0.019(3) -0.007(2) 0.001(3) -0.005(3) C30 0.024(3) 0.028(3) 0.007(3) -0.001(2) 0.003(2) 0.000(3) C31 0.029(3) 0.031(3) 0.016(3) 0.001(2) 0.007(2) -0.006(3) C32 0.029(3) 0.017(3) 0.014(3) -0.003(2) 0.006(2) -0.008(3) C33 0.027(3) 0.022(3) 0.019(3) -0.003(2) 0.003(2) -0.010(3) C34 0.026(3) 0.017(3) 0.038(4) -0.007(3) -0.003(3) -0.006(3) C35 0.037(4) 0.021(3) 0.040(4) -0.003(3) -0.018(3) -0.006(3) C36 0.028(3) 0.021(3) 0.016(3) -0.008(2) 0.005(2) -0.003(3) C37 0.029(3) 0.018(3) 0.029(3) -0.007(3) -0.004(3) 0.004(3) C38 0.031(4) 0.022(3) 0.035(4) 0.004(3) -0.004(3) -0.010(3) C39 0.015(3) 0.020(3) 0.021(3) 0.002(2) 0.000(2) 0.001(2) C40 0.014(3) 0.019(3) 0.013(3) 0.001(2) 0.004(2) 0.000(2) C41 0.017(3) 0.010(3) 0.010(2) 0.006(2) 0.002(2) 0.003(2) C42 0.009(3) 0.018(3) 0.010(3) 0.003(2) -0.001(2) 0.003(2) C43 0.015(3) 0.018(3) 0.009(2) 0.000(2) 0.001(2) 0.004(2) C44 0.015(3) 0.019(3) 0.014(3) -0.005(2) 0.001(2) 0.001(2) C45 0.016(3) 0.017(3) 0.016(3) -0.005(2) -0.001(2) 0.000(2) C46 0.020(3) 0.026(3) 0.022(3) -0.013(2) 0.010(2) -0.010(3) C47 0.032(4) 0.020(3) 0.041(4) -0.011(3) -0.001(3) 0.000(3) C48 0.027(3) 0.012(3) 0.036(3) 0.002(3) 0.000(3) -0.003(3) C49 0.020(3) 0.017(3) 0.012(3) -0.001(2) 0.004(2) -0.005(2) C50 0.020(3) 0.021(3) 0.027(3) -0.003(3) -0.003(2) -0.008(3) C51 0.027(3) 0.018(3) 0.031(3) -0.006(3) -0.005(3) -0.005(3) C52 0.014(3) 0.015(3) 0.022(3) 0.000(2) 0.002(2) 0.001(2) C53 0.011(3) 0.016(3) 0.014(3) -0.001(2) 0.003(2) -0.001(2) C54 0.009(3) 0.019(3) 0.009(2) 0.003(2) -0.0019(19) 0.004(2) C55 0.012(3) 0.016(3) 0.012(3) 0.003(2) 0.001(2) 0.002(2) C56 0.011(3) 0.013(3) 0.012(3) 0.001(2) -0.006(2) 0.003(2) C57 0.014(3) 0.022(3) 0.010(3) -0.001(2) 0.000(2) 0.003(2) C58 0.016(3) 0.022(3) 0.016(3) -0.002(2) -0.006(2) -0.001(2) C59 0.017(3) 0.015(3) 0.014(3) -0.007(2) 0.001(2) -0.001(2) C60 0.029(4) 0.032(4) 0.019(3) 0.005(3) 0.005(3) 0.011(3) C61 0.032(4) 0.040(4) 0.017(3) 0.010(3) 0.000(3) 0.010(3) C62 0.038(4) 0.023(3) 0.017(3) -0.001(2) 0.011(3) -0.003(3) C63 0.035(4) 0.105(7) 0.025(4) 0.003(4) 0.012(3) 0.040(4) C64 0.033(4) 0.086(6) 0.013(3) 0.006(3) 0.002(3) 0.024(4) C65 0.046(5) 0.038(4) 0.044(4) 0.003(3) 0.005(3) -0.002(3) Cl1 0.0473(11) 0.0497(11) 0.0490(11) -0.0028(9) 0.0089(8) -0.0025(9) Cl2 0.0425(12) 0.0810(16) 0.0868(16) 0.0262(13) 0.0075(11) -0.0091(11) Cl3 0.0864(17) 0.0698(15) 0.0487(12) 0.0077(10) 0.0158(11) 0.0088(13) C66 0.071(6) 0.062(6) 0.046(5) 0.000(4) 0.001(4) 0.014(5) Cl4 0.0626(14) 0.0580(13) 0.0525(12) -0.0097(10) 0.0123(9) 0.0069(10) Cl5 0.0667(16) 0.0844(17) 0.0758(16) 0.0044(13) 0.0142(12) 0.0081(13) Cl6 0.0688(16) 0.0681(15) 0.0868(16) -0.0323(13) 0.0056(12) 0.0030(12) C67 0.025(3) 0.030(4) 0.032(3) -0.009(3) 0.003(3) 0.003(3) Cl7 0.0631(13) 0.0467(11) 0.0457(11) 0.0163(9) -0.0113(9) 0.0010(10) Cl8 0.0341(9) 0.0287(8) 0.0252(8) 0.0007(6) 0.0033(6) 0.0070(7) Cl9 0.0465(12) 0.0554(12) 0.0721(13) -0.0150(10) 0.0235(10) 0.0147(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.459(8) . ? C1 C6 1.530(8) . ? C1 H30 0.9900 . ? C1 H31 0.9900 . ? C2 C3 1.534(9) . ? C2 H32 0.9900 . ? C2 H33 0.9900 . ? C3 C26 1.509(7) . ? C3 C4 1.517(8) . ? C3 H34 1.0000 . ? C4 C5 1.421(8) . ? C4 H1 0.9500 . ? C5 C6 1.528(8) . ? C5 H2 0.9500 . ? C6 C7 1.515(7) . ? C6 H35 1.0000 . ? C7 C8 1.358(7) . ? C7 C26 1.439(7) . ? C8 C9 1.448(7) . ? C8 H3 0.9500 . ? C9 C10 1.403(7) . ? C9 C24 1.437(7) . ? C10 C11 1.428(7) . ? C10 C42 1.506(7) . ? C11 C12 1.434(7) . ? C11 C22 1.451(7) . ? C12 C13 1.360(7) . ? C12 H4 0.9500 . ? C13 C20 1.445(7) . ? C13 C14 1.517(7) . ? C14 C19 1.546(8) . ? C14 C15 1.549(8) . ? C14 H36 1.0000 . ? C15 C16 1.414(7) . ? C15 H5 0.9500 . ? C16 C17 1.527(8) . ? C16 H6 0.9500 . ? C17 C20 1.508(7) . ? C17 C18 1.542(8) . ? C17 H37 1.0000 . ? C18 C19 1.442(7) . ? C18 H38 0.9900 . ? C18 H39 0.9900 . ? C19 H40 0.9900 . ? C19 H41 0.9900 . ? C20 C21 1.348(7) . ? C21 C22 1.428(7) . ? C21 H7 0.9500 . ? C22 C23 1.402(7) . ? C23 C24 1.399(7) . ? C23 C27 1.505(6) . ? C24 C25 1.429(7) . ? C25 C26 1.354(7) . ? C25 H8 0.9500 . ? C27 C32 1.374(7) . ? C27 C28 1.380(8) . ? C28 C29 1.389(7) . ? C28 H9 0.9500 . ? C29 C30 1.379(8) . ? C29 H10 0.9500 . ? C30 C31 1.376(8) . ? C30 H11 0.9500 . ? C31 C32 1.395(7) . ? C31 H12 0.9500 . ? C32 H13 0.9500 . ? C33 C39 1.501(7) . ? C33 C38 1.525(8) . ? C33 C34 1.549(8) . ? C33 H42 1.0000 . ? C34 C35 1.411(8) . ? C34 H43 0.9900 . ? C34 H44 0.9900 . ? C35 C36 1.529(8) . ? C35 H45 0.9900 . ? C35 H46 0.9900 . ? C36 C58 1.512(7) . ? C36 C37 1.532(8) . ? C36 H47 1.0000 . ? C37 C38 1.422(8) . ? C37 H14 0.9500 . ? C38 H15 0.9500 . ? C39 C40 1.352(7) . ? C39 C58 1.436(7) . ? C40 C41 1.430(7) . ? C40 H16 0.9500 . ? C41 C42 1.394(7) . ? C41 C56 1.454(7) . ? C42 C43 1.425(7) . ? C43 C44 1.427(7) . ? C43 C54 1.446(7) . ? C44 C45 1.368(7) . ? C44 H17 0.9500 . ? C45 C52 1.438(7) . ? C45 C46 1.509(7) . ? C46 C47 1.530(8) . ? C46 C51 1.535(8) . ? C46 H48 1.0000 . ? C47 C48 1.417(8) . ? C47 H18 0.9500 . ? C48 C49 1.527(8) . ? C48 H19 0.9500 . ? C49 C52 1.508(7) . ? C49 C50 1.533(7) . ? C49 H49 1.0000 . ? C50 C51 1.454(8) . ? C50 H50 0.9900 . ? C50 H51 0.9900 . ? C51 H52 0.9900 . ? C51 H53 0.9900 . ? C52 C53 1.354(7) . ? C53 C54 1.416(7) . ? C53 H20 0.9500 . ? C54 C55 1.413(7) . ? C55 C56 1.397(7) . ? C55 C59 1.500(7) . ? C56 C57 1.423(7) . ? C57 C58 1.366(7) . ? C57 H21 0.9500 . ? C59 C64 1.371(8) . ? C59 C60 1.370(7) . ? C60 C61 1.386(8) . ? C60 H22 0.9500 . ? C61 C62 1.358(8) . ? C61 H23 0.9500 . ? C62 C63 1.369(9) . ? C62 H24 0.9500 . ? C63 C64 1.391(8) . ? C63 H25 0.9500 . ? C64 H26 0.9500 . ? C65 Cl1 1.741(7) . ? C65 Cl3 1.745(7) . ? C65 Cl2 1.771(7) . ? C65 H27 1.0000 . ? C66 Cl6 1.752(8) . ? C66 Cl4 1.759(9) . ? C66 Cl5 1.772(8) . ? C66 H28 1.0000 . ? C67 Cl7 1.728(6) . ? C67 Cl8 1.753(6) . ? C67 Cl9 1.773(6) . ? C67 H29 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 112.9(5) . . ? C2 C1 H30 109.0 . . ? C6 C1 H30 109.0 . . ? C2 C1 H31 109.0 . . ? C6 C1 H31 109.0 . . ? H30 C1 H31 107.8 . . ? C1 C2 C3 110.4(5) . . ? C1 C2 H32 109.6 . . ? C3 C2 H32 109.6 . . ? C1 C2 H33 109.6 . . ? C3 C2 H33 109.6 . . ? H32 C2 H33 108.1 . . ? C26 C3 C4 107.7(5) . . ? C26 C3 C2 106.5(5) . . ? C4 C3 C2 106.0(5) . . ? C26 C3 H34 112.1 . . ? C4 C3 H34 112.1 . . ? C2 C3 H34 112.1 . . ? C5 C4 C3 112.6(5) . . ? C5 C4 H1 123.7 . . ? C3 C4 H1 123.7 . . ? C4 C5 C6 112.4(5) . . ? C4 C5 H2 123.8 . . ? C6 C5 H2 123.8 . . ? C7 C6 C5 106.2(4) . . ? C7 C6 C1 107.6(4) . . ? C5 C6 C1 105.9(4) . . ? C7 C6 H35 112.3 . . ? C5 C6 H35 112.3 . . ? C1 C6 H35 112.3 . . ? C8 C7 C26 120.7(5) . . ? C8 C7 C6 128.1(5) . . ? C26 C7 C6 111.2(4) . . ? C7 C8 C9 121.2(4) . . ? C7 C8 H3 119.4 . . ? C9 C8 H3 119.4 . . ? C10 C9 C24 120.6(4) . . ? C10 C9 C8 122.1(4) . . ? C24 C9 C8 117.3(5) . . ? C9 C10 C11 119.0(4) . . ? C9 C10 C42 122.0(4) . . ? C11 C10 C42 119.0(4) . . ? C10 C11 C12 121.4(4) . . ? C10 C11 C22 119.9(4) . . ? C12 C11 C22 118.6(4) . . ? C13 C12 C11 120.8(4) . . ? C13 C12 H4 119.6 . . ? C11 C12 H4 119.6 . . ? C12 C13 C20 120.6(5) . . ? C12 C13 C14 127.6(4) . . ? C20 C13 C14 111.7(4) . . ? C13 C14 C19 106.2(4) . . ? C13 C14 C15 108.2(4) . . ? C19 C14 C15 105.4(4) . . ? C13 C14 H36 112.2 . . ? C19 C14 H36 112.2 . . ? C15 C14 H36 112.2 . . ? C16 C15 C14 112.4(5) . . ? C16 C15 H5 123.8 . . ? C14 C15 H5 123.8 . . ? C15 C16 C17 112.4(5) . . ? C15 C16 H6 123.8 . . ? C17 C16 H6 123.8 . . ? C20 C17 C16 108.1(4) . . ? C20 C17 C18 106.4(4) . . ? C16 C17 C18 106.1(4) . . ? C20 C17 H37 112.0 . . ? C16 C17 H37 112.0 . . ? C18 C17 H37 112.0 . . ? C19 C18 C17 112.0(4) . . ? C19 C18 H38 109.2 . . ? C17 C18 H38 109.2 . . ? C19 C18 H39 109.2 . . ? C17 C18 H39 109.2 . . ? H38 C18 H39 107.9 . . ? C18 C19 C14 111.5(5) . . ? C18 C19 H40 109.3 . . ? C14 C19 H40 109.3 . . ? C18 C19 H41 109.3 . . ? C14 C19 H41 109.3 . . ? H40 C19 H41 108.0 . . ? C21 C20 C13 119.7(5) . . ? C21 C20 C17 127.7(5) . . ? C13 C20 C17 112.6(5) . . ? C20 C21 C22 122.3(5) . . ? C20 C21 H7 118.8 . . ? C22 C21 H7 118.8 . . ? C23 C22 C21 122.5(4) . . ? C23 C22 C11 119.6(4) . . ? C21 C22 C11 117.9(5) . . ? C24 C23 C22 120.4(4) . . ? C24 C23 C27 119.2(5) . . ? C22 C23 C27 120.4(4) . . ? C23 C24 C25 120.3(4) . . ? C23 C24 C9 120.2(5) . . ? C25 C24 C9 119.4(4) . . ? C26 C25 C24 121.4(5) . . ? C26 C25 H8 119.3 . . ? C24 C25 H8 119.3 . . ? C25 C26 C7 119.7(5) . . ? C25 C26 C3 126.9(5) . . ? C7 C26 C3 113.4(4) . . ? C32 C27 C28 118.8(4) . . ? C32 C27 C23 121.9(5) . . ? C28 C27 C23 119.2(5) . . ? C27 C28 C29 120.9(5) . . ? C27 C28 H9 119.5 . . ? C29 C28 H9 119.5 . . ? C30 C29 C28 119.8(5) . . ? C30 C29 H10 120.1 . . ? C28 C29 H10 120.1 . . ? C31 C30 C29 119.8(5) . . ? C31 C30 H11 120.1 . . ? C29 C30 H11 120.1 . . ? C30 C31 C32 119.9(5) . . ? C30 C31 H12 120.1 . . ? C32 C31 H12 120.1 . . ? C27 C32 C31 120.8(5) . . ? C27 C32 H13 119.6 . . ? C31 C32 H13 119.6 . . ? C39 C33 C38 107.3(5) . . ? C39 C33 C34 106.5(4) . . ? C38 C33 C34 106.1(4) . . ? C39 C33 H42 112.2 . . ? C38 C33 H42 112.2 . . ? C34 C33 H42 112.2 . . ? C35 C34 C33 111.6(5) . . ? C35 C34 H43 109.3 . . ? C33 C34 H43 109.3 . . ? C35 C34 H44 109.3 . . ? C33 C34 H44 109.3 . . ? H43 C34 H44 108.0 . . ? C34 C35 C36 113.2(5) . . ? C34 C35 H45 108.9 . . ? C36 C35 H45 108.9 . . ? C34 C35 H46 108.9 . . ? C36 C35 H46 108.9 . . ? H45 C35 H46 107.8 . . ? C58 C36 C35 105.9(4) . . ? C58 C36 C37 107.1(4) . . ? C35 C36 C37 105.9(5) . . ? C58 C36 H47 112.5 . . ? C35 C36 H47 112.5 . . ? C37 C36 H47 112.5 . . ? C38 C37 C36 112.2(5) . . ? C38 C37 H14 123.9 . . ? C36 C37 H14 123.9 . . ? C37 C38 C33 112.4(5) . . ? C37 C38 H15 123.8 . . ? C33 C38 H15 123.8 . . ? C40 C39 C58 121.2(5) . . ? C40 C39 C33 126.8(5) . . ? C58 C39 C33 112.1(5) . . ? C39 C40 C41 121.1(5) . . ? C39 C40 H16 119.5 . . ? C41 C40 H16 119.5 . . ? C42 C41 C40 121.6(4) . . ? C42 C41 C56 120.4(5) . . ? C40 C41 C56 118.0(4) . . ? C41 C42 C43 119.7(4) . . ? C41 C42 C10 120.6(4) . . ? C43 C42 C10 119.6(4) . . ? C42 C43 C44 121.4(4) . . ? C42 C43 C54 119.8(5) . . ? C44 C43 C54 118.8(5) . . ? C45 C44 C43 120.9(5) . . ? C45 C44 H17 119.6 . . ? C43 C44 H17 119.6 . . ? C44 C45 C52 119.9(5) . . ? C44 C45 C46 128.0(5) . . ? C52 C45 C46 112.0(5) . . ? C45 C46 C47 107.3(4) . . ? C45 C46 C51 106.8(4) . . ? C47 C46 C51 106.5(5) . . ? C45 C46 H48 111.9 . . ? C47 C46 H48 111.9 . . ? C51 C46 H48 111.9 . . ? C48 C47 C46 112.2(5) . . ? C48 C47 H18 123.9 . . ? C46 C47 H18 123.9 . . ? C47 C48 C49 112.3(5) . . ? C47 C48 H19 123.9 . . ? C49 C48 H19 123.9 . . ? C52 C49 C48 107.3(4) . . ? C52 C49 C50 106.5(4) . . ? C48 C49 C50 106.8(4) . . ? C52 C49 H49 112.0 . . ? C48 C49 H49 112.0 . . ? C50 C49 H49 112.0 . . ? C51 C50 C49 111.5(5) . . ? C51 C50 H50 109.3 . . ? C49 C50 H50 109.3 . . ? C51 C50 H51 109.3 . . ? C49 C50 H51 109.3 . . ? H50 C50 H51 108.0 . . ? C50 C51 C46 111.4(5) . . ? C50 C51 H52 109.4 . . ? C46 C51 H52 109.4 . . ? C50 C51 H53 109.4 . . ? C46 C51 H53 109.4 . . ? H52 C51 H53 108.0 . . ? C53 C52 C45 120.3(5) . . ? C53 C52 C49 127.4(5) . . ? C45 C52 C49 112.3(4) . . ? C52 C53 C54 121.8(5) . . ? C52 C53 H20 119.1 . . ? C54 C53 H20 119.1 . . ? C55 C54 C53 121.9(4) . . ? C55 C54 C43 119.8(5) . . ? C53 C54 C43 118.3(4) . . ? C56 C55 C54 120.4(4) . . ? C56 C55 C59 120.3(4) . . ? C54 C55 C59 119.4(4) . . ? C55 C56 C57 121.2(4) . . ? C55 C56 C41 119.8(4) . . ? C57 C56 C41 119.0(5) . . ? C58 C57 C56 121.1(5) . . ? C58 C57 H21 119.5 . . ? C56 C57 H21 119.5 . . ? C57 C58 C39 119.7(5) . . ? C57 C58 C36 127.6(5) . . ? C39 C58 C36 112.6(5) . . ? C64 C59 C60 117.4(5) . . ? C64 C59 C55 121.8(5) . . ? C60 C59 C55 120.7(5) . . ? C59 C60 C61 121.2(6) . . ? C59 C60 H22 119.4 . . ? C61 C60 H22 119.4 . . ? C62 C61 C60 121.1(5) . . ? C62 C61 H23 119.4 . . ? C60 C61 H23 119.4 . . ? C61 C62 C63 118.4(5) . . ? C61 C62 H24 120.8 . . ? C63 C62 H24 120.8 . . ? C62 C63 C64 120.5(6) . . ? C62 C63 H25 119.7 . . ? C64 C63 H25 119.7 . . ? C59 C64 C63 121.3(6) . . ? C59 C64 H26 119.4 . . ? C63 C64 H26 119.4 . . ? Cl1 C65 Cl3 111.6(4) . . ? Cl1 C65 Cl2 111.0(4) . . ? Cl3 C65 Cl2 110.0(4) . . ? Cl1 C65 H27 108.1 . . ? Cl3 C65 H27 108.1 . . ? Cl2 C65 H27 108.1 . . ? Cl6 C66 Cl4 109.4(5) . . ? Cl6 C66 Cl5 109.5(5) . . ? Cl4 C66 Cl5 110.4(4) . . ? Cl6 C66 H28 109.2 . . ? Cl4 C66 H28 109.2 . . ? Cl5 C66 H28 109.2 . . ? Cl7 C67 Cl8 112.0(3) . . ? Cl7 C67 Cl9 110.6(3) . . ? Cl8 C67 Cl9 109.2(3) . . ? Cl7 C67 H29 108.3 . . ? Cl8 C67 H29 108.3 . . ? Cl9 C67 H29 108.3 . . ? 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 C6 C1 C2 C3 1.8(7) . . . . ? C1 C2 C3 C26 55.8(6) . . . . ? C1 C2 C3 C4 -58.7(6) . . . . ? C26 C3 C4 C5 -55.3(6) . . . . ? C2 C3 C4 C5 58.4(6) . . . . ? C3 C4 C5 C6 0.3(7) . . . . ? C4 C5 C6 C7 57.0(6) . . . . ? C4 C5 C6 C1 -57.2(6) . . . . ? C2 C1 C6 C7 -57.6(6) . . . . ? C2 C1 C6 C5 55.6(6) . . . . ? C5 C6 C7 C8 118.7(6) . . . . ? C1 C6 C7 C8 -128.3(6) . . . . ? C5 C6 C7 C26 -59.4(6) . . . . ? C1 C6 C7 C26 53.6(6) . . . . ? C26 C7 C8 C9 -3.0(8) . . . . ? C6 C7 C8 C9 179.0(5) . . . . ? C7 C8 C9 C10 177.9(5) . . . . ? C7 C8 C9 C24 -2.4(7) . . . . ? C24 C9 C10 C11 0.3(7) . . . . ? C8 C9 C10 C11 -179.9(5) . . . . ? C24 C9 C10 C42 178.8(5) . . . . ? C8 C9 C10 C42 -1.5(8) . . . . ? C9 C10 C11 C12 178.6(5) . . . . ? C42 C10 C11 C12 0.1(7) . . . . ? C9 C10 C11 C22 -3.0(7) . . . . ? C42 C10 C11 C22 178.5(5) . . . . ? C10 C11 C12 C13 176.9(5) . . . . ? C22 C11 C12 C13 -1.5(7) . . . . ? C11 C12 C13 C20 -0.3(8) . . . . ? C11 C12 C13 C14 -178.3(5) . . . . ? C12 C13 C14 C19 119.2(6) . . . . ? C20 C13 C14 C19 -58.9(6) . . . . ? C12 C13 C14 C15 -128.1(6) . . . . ? C20 C13 C14 C15 53.8(6) . . . . ? C13 C14 C15 C16 -55.8(6) . . . . ? C19 C14 C15 C16 57.5(6) . . . . ? C14 C15 C16 C17 0.7(7) . . . . ? C15 C16 C17 C20 55.6(6) . . . . ? C15 C16 C17 C18 -58.2(6) . . . . ? C20 C17 C18 C19 -58.0(6) . . . . ? C16 C17 C18 C19 57.0(6) . . . . ? C17 C18 C19 C14 1.3(7) . . . . ? C13 C14 C19 C18 56.7(6) . . . . ? C15 C14 C19 C18 -57.9(6) . . . . ? C12 C13 C20 C21 2.2(8) . . . . ? C14 C13 C20 C21 -179.5(5) . . . . ? C12 C13 C20 C17 -176.3(5) . . . . ? C14 C13 C20 C17 2.0(6) . . . . ? C16 C17 C20 C21 124.4(6) . . . . ? C18 C17 C20 C21 -122.1(6) . . . . ? C16 C17 C20 C13 -57.3(6) . . . . ? C18 C17 C20 C13 56.3(6) . . . . ? C13 C20 C21 C22 -2.2(8) . . . . ? C17 C20 C21 C22 176.0(5) . . . . ? C20 C21 C22 C23 -178.0(5) . . . . ? C20 C21 C22 C11 0.5(8) . . . . ? C10 C11 C22 C23 1.4(7) . . . . ? C12 C11 C22 C23 179.9(5) . . . . ? C10 C11 C22 C21 -177.0(5) . . . . ? C12 C11 C22 C21 1.4(7) . . . . ? C21 C22 C23 C24 -178.7(5) . . . . ? C11 C22 C23 C24 2.9(8) . . . . ? C21 C22 C23 C27 4.0(8) . . . . ? C11 C22 C23 C27 -174.4(5) . . . . ? C22 C23 C24 C25 173.4(5) . . . . ? C27 C23 C24 C25 -9.2(7) . . . . ? C22 C23 C24 C9 -5.6(8) . . . . ? C27 C23 C24 C9 171.7(5) . . . . ? C10 C9 C24 C23 4.0(7) . . . . ? C8 C9 C24 C23 -175.7(5) . . . . ? C10 C9 C24 C25 -175.0(5) . . . . ? C8 C9 C24 C25 5.2(7) . . . . ? C23 C24 C25 C26 178.2(5) . . . . ? C9 C24 C25 C26 -2.8(8) . . . . ? C24 C25 C26 C7 -2.7(8) . . . . ? C24 C25 C26 C3 176.4(5) . . . . ? C8 C7 C26 C25 5.7(8) . . . . ? C6 C7 C26 C25 -176.0(5) . . . . ? C8 C7 C26 C3 -173.6(5) . . . . ? C6 C7 C26 C3 4.7(7) . . . . ? C4 C3 C26 C25 -126.6(6) . . . . ? C2 C3 C26 C25 120.1(6) . . . . ? C4 C3 C26 C7 52.6(6) . . . . ? C2 C3 C26 C7 -60.8(6) . . . . ? C24 C23 C27 C32 96.6(6) . . . . ? C22 C23 C27 C32 -86.0(7) . . . . ? C24 C23 C27 C28 -80.4(6) . . . . ? C22 C23 C27 C28 97.0(6) . . . . ? C32 C27 C28 C29 0.7(8) . . . . ? C23 C27 C28 C29 177.7(5) . . . . ? C27 C28 C29 C30 -1.3(9) . . . . ? C28 C29 C30 C31 1.7(9) . . . . ? C29 C30 C31 C32 -1.4(9) . . . . ? C28 C27 C32 C31 -0.3(8) . . . . ? C23 C27 C32 C31 -177.3(5) . . . . ? C30 C31 C32 C27 0.7(9) . . . . ? C39 C33 C34 C35 56.5(6) . . . . ? C38 C33 C34 C35 -57.6(6) . . . . ? C33 C34 C35 C36 0.9(7) . . . . ? C34 C35 C36 C58 -57.1(6) . . . . ? C34 C35 C36 C37 56.4(6) . . . . ? C58 C36 C37 C38 55.0(6) . . . . ? C35 C36 C37 C38 -57.6(6) . . . . ? C36 C37 C38 C33 1.2(7) . . . . ? C39 C33 C38 C37 -57.3(6) . . . . ? C34 C33 C38 C37 56.3(6) . . . . ? C38 C33 C39 C40 -123.3(6) . . . . ? C34 C33 C39 C40 123.4(6) . . . . ? C38 C33 C39 C58 56.3(6) . . . . ? C34 C33 C39 C58 -57.0(6) . . . . ? C58 C39 C40 C41 1.0(8) . . . . ? C33 C39 C40 C41 -179.5(5) . . . . ? C39 C40 C41 C42 -178.9(5) . . . . ? C39 C40 C41 C56 0.3(7) . . . . ? C40 C41 C42 C43 -177.2(5) . . . . ? C56 C41 C42 C43 3.6(7) . . . . ? C40 C41 C42 C10 3.6(7) . . . . ? C56 C41 C42 C10 -175.6(4) . . . . ? C9 C10 C42 C41 -93.2(6) . . . . ? C11 C10 C42 C41 85.2(6) . . . . ? C9 C10 C42 C43 87.6(6) . . . . ? C11 C10 C42 C43 -94.0(6) . . . . ? C41 C42 C43 C44 180.0(5) . . . . ? C10 C42 C43 C44 -0.8(7) . . . . ? C41 C42 C43 C54 -1.3(7) . . . . ? C10 C42 C43 C54 177.9(4) . . . . ? C42 C43 C44 C45 179.7(5) . . . . ? C54 C43 C44 C45 0.9(8) . . . . ? C43 C44 C45 C52 -0.1(8) . . . . ? C43 C44 C45 C46 179.5(5) . . . . ? C44 C45 C46 C47 -123.4(6) . . . . ? C52 C45 C46 C47 56.3(6) . . . . ? C44 C45 C46 C51 122.7(6) . . . . ? C52 C45 C46 C51 -57.6(6) . . . . ? C45 C46 C47 C48 -56.3(6) . . . . ? C51 C46 C47 C48 57.8(6) . . . . ? C46 C47 C48 C49 -0.1(7) . . . . ? C47 C48 C49 C52 56.4(6) . . . . ? C47 C48 C49 C50 -57.5(6) . . . . ? C52 C49 C50 C51 -57.5(6) . . . . ? C48 C49 C50 C51 56.8(6) . . . . ? C49 C50 C51 C46 0.4(7) . . . . ? C45 C46 C51 C50 57.0(6) . . . . ? C47 C46 C51 C50 -57.5(6) . . . . ? C44 C45 C52 C53 -0.3(8) . . . . ? C46 C45 C52 C53 -180.0(5) . . . . ? C44 C45 C52 C49 179.6(5) . . . . ? C46 C45 C52 C49 -0.1(6) . . . . ? C48 C49 C52 C53 123.6(6) . . . . ? C50 C49 C52 C53 -122.3(6) . . . . ? C48 C49 C52 C45 -56.3(6) . . . . ? C50 C49 C52 C45 57.8(6) . . . . ? C45 C52 C53 C54 -0.2(8) . . . . ? C49 C52 C53 C54 179.9(5) . . . . ? C52 C53 C54 C55 -177.3(5) . . . . ? C52 C53 C54 C43 1.0(7) . . . . ? C42 C43 C54 C55 -1.8(7) . . . . ? C44 C43 C54 C55 177.0(5) . . . . ? C42 C43 C54 C53 179.9(5) . . . . ? C44 C43 C54 C53 -1.4(7) . . . . ? C53 C54 C55 C56 -179.2(5) . . . . ? C43 C54 C55 C56 2.5(7) . . . . ? C53 C54 C55 C59 1.2(7) . . . . ? C43 C54 C55 C59 -177.1(5) . . . . ? C54 C55 C56 C57 178.7(5) . . . . ? C59 C55 C56 C57 -1.6(7) . . . . ? C54 C55 C56 C41 -0.2(7) . . . . ? C59 C55 C56 C41 179.4(5) . . . . ? C42 C41 C56 C55 -2.9(7) . . . . ? C40 C41 C56 C55 177.9(5) . . . . ? C42 C41 C56 C57 178.1(5) . . . . ? C40 C41 C56 C57 -1.1(7) . . . . ? C55 C56 C57 C58 -178.4(5) . . . . ? C41 C56 C57 C58 0.6(7) . . . . ? C56 C57 C58 C39 0.6(8) . . . . ? C56 C57 C58 C36 179.0(5) . . . . ? C40 C39 C58 C57 -1.4(8) . . . . ? C33 C39 C58 C57 179.0(5) . . . . ? C40 C39 C58 C36 179.9(5) . . . . ? C33 C39 C58 C36 0.3(7) . . . . ? C35 C36 C58 C57 -121.9(6) . . . . ? C37 C36 C58 C57 125.4(6) . . . . ? C35 C36 C58 C39 56.6(6) . . . . ? C37 C36 C58 C39 -56.1(6) . . . . ? C56 C55 C59 C64 -91.0(7) . . . . ? C54 C55 C59 C64 88.6(7) . . . . ? C56 C55 C59 C60 85.8(7) . . . . ? C54 C55 C59 C60 -94.5(6) . . . . ? C64 C59 C60 C61 -2.5(9) . . . . ? C55 C59 C60 C61 -179.4(5) . . . . ? C59 C60 C61 C62 2.7(10) . . . . ? C60 C61 C62 C63 -1.0(10) . . . . ? C61 C62 C63 C64 -0.7(12) . . . . ? C60 C59 C64 C63 0.7(11) . . . . ? C55 C59 C64 C63 177.6(7) . . . . ? C62 C63 C64 C59 0.9(13) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.783 _refine_diff_density_min -0.711 _refine_diff_density_rms 0.101 _database_code_depnum_ccdc_archive 'CCDC 923853' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl5 #TrackingRef '8bBPCF3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C68 H46 F12, 4(C H Cl3) ' _chemical_formula_sum 'C72 H50 Cl12 F12' _chemical_formula_weight 1568.52 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 24.6901(5) _cell_length_b 21.1291(5) _cell_length_c 17.5492(4) _cell_angle_alpha 90.00 _cell_angle_beta 130.4530(10) _cell_angle_gamma 90.00 _cell_volume 6966.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 30347 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 25.39 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3176 _exptl_absorpt_coefficient_mu 0.552 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9317 _exptl_absorpt_correction_T_max 0.9469 _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48911 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.35 _reflns_number_total 6362 _reflns_number_gt 4725 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1354P)^2^+6.3719P] 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 6362 _refine_ls_number_parameters 530 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.2151 _refine_ls_wR_factor_gt 0.2002 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.5185(3) 0.1895(2) 0.5622(5) 0.0460(19) Uani 0.43(3) 1 d P A 1 Cl2 Cl 0.4239(3) 0.2660(2) 0.3823(6) 0.0487(19) Uani 0.43(3) 1 d P A 1 Cl3 Cl 0.5349(10) 0.3243(6) 0.5879(12) 0.082(2) Uani 0.43(3) 1 d P A 1 Cl7 Cl 0.5181(4) 0.1984(6) 0.5710(7) 0.115(3) Uani 0.57(3) 1 d P A 2 Cl8 Cl 0.4148(6) 0.2720(3) 0.4037(8) 0.105(3) Uani 0.57(3) 1 d P A 2 Cl9 Cl 0.5341(7) 0.3336(7) 0.5644(13) 0.111(3) Uani 0.57(3) 1 d P A 2 Cl4 Cl 0.74640(10) -0.05770(9) 0.99451(16) 0.0965(8) Uani 0.793(5) 1 d P B 1 Cl5 Cl 0.85031(8) -0.01162(10) 0.98418(14) 0.0659(5) Uani 0.793(5) 1 d P B 1 Cl6 Cl 0.75760(11) 0.07554(10) 0.9822(3) 0.1139(11) Uani 0.793(5) 1 d P B 1 Cl10 Cl 0.7586(4) 0.0897(3) 0.9270(7) 0.079(2) Uani 0.207(5) 1 d PD B 2 Cl11 Cl 0.7312(6) -0.0062(6) 1.0022(9) 0.148(5) Uiso 0.207(5) 1 d PD B 2 Cl12 Cl 0.8447(6) -0.0209(6) 1.0025(9) 0.101(4) Uiso 0.207(5) 1 d PD B 2 F1 F 0.3354(13) -0.2452(16) 0.1530(16) 0.142(9) Uani 0.45(5) 1 d P C 5 F2 F 0.3711(18) -0.3002(13) 0.094(3) 0.128(10) Uani 0.45(5) 1 d P C 5 F3 F 0.3251(11) -0.2161(10) 0.023(2) 0.099(5) Uani 0.45(5) 1 d P C 5 F7 F 0.3757(16) -0.3061(10) 0.131(2) 0.113(6) Uani 0.55(5) 1 d P C 6 F8 F 0.3349(15) -0.2351(17) 0.0291(18) 0.156(10) Uani 0.55(5) 1 d P C 6 F9 F 0.3226(7) -0.2290(7) 0.1289(16) 0.109(5) Uani 0.55(5) 1 d PU C 6 F4 F 0.6056(14) 0.4649(10) 0.1706(18) 0.086(6) Uani 0.37(5) 1 d P D 7 F6 F 0.6110(8) 0.5443(15) 0.2383(15) 0.083(6) Uani 0.37(5) 1 d P D 7 F10 F 0.6214(12) 0.4786(14) 0.216(4) 0.161(10) Uani 0.63(5) 1 d P D 8 F11 F 0.5905(17) 0.5655(10) 0.2389(10) 0.116(6) Uani 0.63(5) 1 d P D 8 F5 F 0.52112(16) 0.52241(15) 0.0938(2) 0.0938(9) Uani 1 1 d . D . C1 C 0.5000 -0.03946(17) 0.2500 0.0292(8) Uani 1 2 d S . . C2 C 0.53720(13) -0.00618(12) 0.2267(2) 0.0289(6) Uani 1 1 d . . . C3 C 0.57300(14) -0.03784(13) 0.1980(2) 0.0315(6) Uani 1 1 d . . . H3 H 0.5733 -0.0828 0.1967 0.038 Uiso 1 1 calc R . . C4 C 0.60641(14) -0.00493(13) 0.1727(2) 0.0317(6) Uani 1 1 d . . . C5 C 0.64267(15) -0.03208(14) 0.1364(2) 0.0382(7) Uani 1 1 d . . . H5 H 0.6414 -0.0794 0.1349 0.046 Uiso 1 1 calc R . . C6 C 0.71897(16) -0.00673(15) 0.2046(2) 0.0418(7) Uani 1 1 d . . . H6 H 0.7600 -0.0329 0.2399 0.050 Uiso 1 1 calc R . . C7 C 0.72128(16) 0.06012(15) 0.2089(2) 0.0410(7) Uani 1 1 d . . . H7 H 0.7642 0.0839 0.2480 0.049 Uiso 1 1 calc R . . C8 C 0.64683(15) 0.09017(13) 0.1435(2) 0.0367(7) Uani 1 1 d . . . H8 H 0.6490 0.1374 0.1472 0.044 Uiso 1 1 calc R . . C9 C 0.60798(14) 0.06301(13) 0.1752(2) 0.0313(6) Uani 1 1 d . . . C10 C 0.57426(14) 0.09497(12) 0.2012(2) 0.0302(6) Uani 1 1 d . . . H10 H 0.5752 0.1399 0.2022 0.036 Uiso 1 1 calc R . . C11 C 0.53731(13) 0.06228(12) 0.22700(19) 0.0283(6) Uani 1 1 d . . . C12 C 0.5000 0.09536(17) 0.2500 0.0273(8) Uani 1 2 d S . . C13 C 0.60487(17) -0.00387(16) 0.0322(2) 0.0435(7) Uani 1 1 d . . . H13A H 0.6278 -0.0197 0.0060 0.052 Uiso 1 1 calc R . . H13B H 0.5545 -0.0177 -0.0142 0.052 Uiso 1 1 calc R . . C14 C 0.60785(17) 0.06590(15) 0.0360(2) 0.0420(7) Uani 1 1 d . . . H14A H 0.5589 0.0832 -0.0098 0.050 Uiso 1 1 calc R . . H14B H 0.6330 0.0811 0.0128 0.050 Uiso 1 1 calc R . . C15 C 0.5000 0.16624(16) 0.2500 0.0268(8) Uani 1 2 d S . . C16 C 0.55232(14) 0.19949(12) 0.3395(2) 0.0285(6) Uani 1 1 d . . . C17 C 0.60614(14) 0.16727(12) 0.4308(2) 0.0308(6) Uani 1 1 d . . . H17 H 0.6063 0.1223 0.4323 0.037 Uiso 1 1 calc R . . C18 C 0.65716(15) 0.19985(13) 0.5157(2) 0.0328(6) Uani 1 1 d . . . C19 C 0.71951(15) 0.17265(14) 0.6165(2) 0.0373(7) Uani 1 1 d . . . H19 H 0.7188 0.1253 0.6165 0.045 Uiso 1 1 calc R . . C20 C 0.71814(17) 0.20062(15) 0.6957(2) 0.0427(7) Uani 1 1 d . . . H20 H 0.7171 0.1759 0.7399 0.051 Uiso 1 1 calc R . . C21 C 0.71863(18) 0.26800(16) 0.6953(2) 0.0462(8) Uani 1 1 d . . . H21 H 0.7177 0.2935 0.7391 0.055 Uiso 1 1 calc R . . C22 C 0.72083(17) 0.29472(14) 0.6159(2) 0.0414(7) Uani 1 1 d . . . H22 H 0.7205 0.3420 0.6150 0.050 Uiso 1 1 calc R . . C23 C 0.65813(15) 0.26705(13) 0.5159(2) 0.0342(6) Uani 1 1 d . . . C24 C 0.60717(15) 0.30028(13) 0.4306(2) 0.0342(6) Uani 1 1 d . . . H24 H 0.6080 0.3452 0.4319 0.041 Uiso 1 1 calc R . . C25 C 0.55245(14) 0.26776(12) 0.3390(2) 0.0294(6) Uani 1 1 d . . . C26 C 0.5000 0.30040(17) 0.2500 0.0311(8) Uani 1 2 d S . . C27 C 0.78701(16) 0.19886(16) 0.6396(2) 0.0441(7) Uani 1 1 d . . . H27A H 0.8295 0.1833 0.7059 0.053 Uiso 1 1 calc R . . H27B H 0.7895 0.1831 0.5888 0.053 Uiso 1 1 calc R . . C28 C 0.78745(17) 0.26755(15) 0.6394(2) 0.0454(8) Uani 1 1 d . . . H28A H 0.7905 0.2827 0.5889 0.054 Uiso 1 1 calc R . . H28B H 0.8300 0.2830 0.7059 0.054 Uiso 1 1 calc R . . C29 C 0.5000 -0.2429(2) 0.2500 0.0506(12) Uani 1 2 d S . . H29 H 0.5000 -0.2879 0.2500 0.061 Uiso 1 2 calc SR . . C30 C 0.43704(18) -0.20989(14) 0.1863(3) 0.0440(8) Uani 1 1 d . C . C31 C 0.43660(15) -0.14418(13) 0.1857(2) 0.0366(7) Uani 1 1 d . . . H31 H 0.3927 -0.1222 0.1410 0.044 Uiso 1 1 calc R . . C32 C 0.5000 -0.11005(17) 0.2500 0.0308(8) Uani 1 2 d S . . C33 C 0.3668(2) -0.24390(17) 0.1159(4) 0.0616(11) Uani 1 1 d . . . C34 C 0.5000 0.5035(2) 0.2500 0.0608(16) Uani 1 2 d S . . H34 H 0.5000 0.5484 0.2500 0.073 Uiso 1 2 calc SR . . C35 C 0.53242(17) 0.47069(15) 0.2211(3) 0.0509(9) Uani 1 1 d . D . C36 C 0.53206(15) 0.40463(14) 0.2200(2) 0.0409(7) Uani 1 1 d . . . H36 H 0.5536 0.3823 0.1987 0.049 Uiso 1 1 calc R . . C37 C 0.5000 0.37166(18) 0.2500 0.0348(9) Uani 1 2 d S . . C38 C 0.5664(2) 0.5050(2) 0.1870(4) 0.0789(15) Uani 1 1 d . . . C39 C 0.5077(2) 0.26178(17) 0.5025(3) 0.0565(9) Uani 1 1 d . . . H39 H 0.5431 0.2607 0.4923 0.068 Uiso 1 1 calc R A 1 C40 C 0.7648(2) 0.00271(19) 0.9446(3) 0.0619(10) Uani 1 1 d D . . H40 H 0.7290 0.0004 0.8698 0.074 Uiso 1 1 calc R B 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 Cl1 0.050(2) 0.032(3) 0.050(2) 0.0086(14) 0.0305(19) 0.0034(11) Cl2 0.048(2) 0.0352(19) 0.053(2) 0.0011(12) 0.0286(15) -0.0006(10) Cl3 0.104(3) 0.047(2) 0.096(4) -0.022(3) 0.065(3) -0.0137(18) Cl7 0.102(4) 0.146(6) 0.098(4) 0.042(3) 0.065(3) -0.004(3) Cl8 0.107(3) 0.071(2) 0.068(3) 0.0071(17) 0.026(2) 0.006(2) Cl9 0.100(3) 0.088(6) 0.125(7) -0.064(5) 0.064(5) -0.023(4) Cl4 0.1125(14) 0.0823(13) 0.1397(17) 0.0207(10) 0.1018(14) 0.0050(9) Cl5 0.0397(7) 0.0908(12) 0.0526(9) 0.0136(7) 0.0234(7) 0.0014(6) Cl6 0.0674(10) 0.0560(10) 0.140(2) -0.0260(13) 0.0321(13) 0.0023(8) Cl10 0.070(4) 0.053(3) 0.078(5) -0.020(3) 0.032(3) 0.000(3) F1 0.089(10) 0.25(2) 0.096(8) -0.024(10) 0.063(7) -0.088(11) F2 0.089(7) 0.046(12) 0.16(2) -0.058(13) 0.044(13) -0.026(8) F3 0.067(6) 0.061(7) 0.077(8) -0.007(4) 0.006(5) -0.036(5) F7 0.098(7) 0.035(4) 0.147(15) -0.012(7) 0.054(11) -0.033(4) F8 0.150(15) 0.16(2) 0.063(7) -0.019(11) 0.027(9) -0.113(14) F9 0.054(4) 0.085(6) 0.164(11) -0.071(6) 0.060(6) -0.040(4) F4 0.107(12) 0.060(7) 0.139(12) 0.022(8) 0.101(11) 0.003(6) F6 0.069(9) 0.056(10) 0.100(7) -0.011(7) 0.044(6) -0.040(6) F10 0.089(8) 0.145(14) 0.27(2) 0.126(14) 0.124(14) 0.034(8) F11 0.179(12) 0.055(7) 0.100(5) -0.013(4) 0.083(7) -0.065(8) F5 0.0882(19) 0.103(2) 0.0770(18) 0.0178(16) 0.0476(16) -0.0187(16) C1 0.0271(18) 0.0227(18) 0.0255(18) 0.000 0.0115(15) 0.000 C2 0.0244(13) 0.0221(13) 0.0290(14) -0.0011(10) 0.0123(11) 0.0007(10) C3 0.0296(13) 0.0221(13) 0.0332(14) -0.0023(11) 0.0161(12) 0.0011(10) C4 0.0257(13) 0.0285(14) 0.0322(15) -0.0021(11) 0.0149(12) 0.0024(10) C5 0.0356(15) 0.0297(14) 0.0489(18) -0.0048(13) 0.0273(14) 0.0013(12) C6 0.0317(15) 0.0437(17) 0.0438(18) -0.0013(13) 0.0217(14) 0.0042(12) C7 0.0324(15) 0.0430(17) 0.0457(18) -0.0100(14) 0.0245(14) -0.0040(12) C8 0.0395(15) 0.0294(14) 0.0460(17) -0.0033(12) 0.0298(14) -0.0019(12) C9 0.0279(13) 0.0284(14) 0.0307(14) -0.0029(11) 0.0160(12) -0.0001(10) C10 0.0315(13) 0.0205(12) 0.0330(14) -0.0016(10) 0.0185(12) -0.0001(10) C11 0.0281(13) 0.0217(13) 0.0268(13) -0.0007(10) 0.0141(11) 0.0003(10) C12 0.0265(17) 0.0215(17) 0.0265(18) 0.000 0.0140(15) 0.000 C13 0.0384(16) 0.0513(19) 0.0381(17) -0.0121(14) 0.0237(14) -0.0031(13) C14 0.0448(17) 0.0429(17) 0.0409(17) 0.0038(13) 0.0290(15) 0.0080(13) C15 0.0268(18) 0.0211(17) 0.033(2) 0.000 0.0197(16) 0.000 C16 0.0300(14) 0.0221(13) 0.0331(15) -0.0012(10) 0.0203(12) -0.0007(10) C17 0.0322(14) 0.0206(13) 0.0373(15) 0.0011(11) 0.0215(13) -0.0008(10) C18 0.0349(14) 0.0295(14) 0.0343(15) -0.0002(11) 0.0226(13) -0.0031(11) C19 0.0337(15) 0.0302(14) 0.0346(15) 0.0016(12) 0.0161(13) -0.0047(11) C20 0.0436(17) 0.0405(17) 0.0356(16) -0.0017(13) 0.0220(14) -0.0086(13) C21 0.0497(19) 0.0469(18) 0.0354(17) -0.0088(13) 0.0246(15) -0.0111(14) C22 0.0464(17) 0.0294(15) 0.0374(17) -0.0041(12) 0.0222(15) -0.0105(13) C23 0.0353(15) 0.0290(14) 0.0349(15) -0.0039(11) 0.0213(13) -0.0075(11) C24 0.0412(16) 0.0224(13) 0.0408(16) -0.0033(11) 0.0274(14) -0.0047(11) C25 0.0313(14) 0.0217(13) 0.0350(15) -0.0009(11) 0.0215(13) -0.0019(10) C26 0.037(2) 0.0191(18) 0.040(2) 0.000 0.0266(19) 0.000 C27 0.0354(16) 0.0471(18) 0.0364(16) 0.0026(13) 0.0173(14) -0.0054(13) C28 0.0398(17) 0.0465(18) 0.0353(16) -0.0032(13) 0.0179(14) -0.0149(14) C29 0.065(3) 0.0193(19) 0.069(3) 0.000 0.044(3) 0.000 C30 0.0511(19) 0.0279(15) 0.0491(19) -0.0069(13) 0.0307(16) -0.0089(13) C31 0.0381(16) 0.0265(14) 0.0368(16) -0.0016(11) 0.0206(13) -0.0027(11) C32 0.034(2) 0.0226(18) 0.032(2) 0.000 0.0194(17) 0.000 C33 0.061(2) 0.037(2) 0.071(3) -0.0134(18) 0.036(2) -0.0156(17) C34 0.043(3) 0.020(2) 0.065(3) 0.000 0.011(2) 0.000 C35 0.0371(16) 0.0287(16) 0.052(2) 0.0125(14) 0.0137(15) -0.0041(13) C36 0.0353(15) 0.0310(15) 0.0429(17) 0.0067(12) 0.0193(14) 0.0005(12) C37 0.031(2) 0.0218(19) 0.038(2) 0.000 0.0162(18) 0.000 C38 0.054(3) 0.049(2) 0.094(3) 0.031(2) 0.030(2) -0.009(2) C39 0.068(2) 0.046(2) 0.061(2) -0.0058(16) 0.044(2) -0.0068(16) C40 0.050(2) 0.066(2) 0.056(2) -0.0026(18) 0.0287(19) -0.0043(17) _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 Cl1 C39 1.770(6) . ? Cl2 C39 1.753(7) . ? Cl3 C39 1.770(16) . ? Cl7 C39 1.703(9) . ? Cl8 C39 1.774(11) . ? Cl9 C39 1.729(12) . ? Cl4 C40 1.767(4) . ? Cl5 C40 1.768(4) . ? Cl6 C40 1.729(5) . ? Cl10 C40 1.854(8) . ? Cl11 C40 1.685(11) . ? Cl12 C40 1.603(11) . ? F1 C33 1.298(17) . ? F2 C33 1.27(3) . ? F3 C33 1.38(3) . ? F7 C33 1.33(2) . ? F8 C33 1.19(3) . ? F9 C33 1.290(12) . ? F4 C38 1.45(2) . ? F6 C38 1.19(2) . ? F10 C38 1.232(16) . ? F11 C38 1.455(18) . ? F5 C38 1.298(5) . ? C1 C2 1.412(3) . ? C1 C2 1.412(3) 2_655 ? C1 C32 1.492(5) . ? C2 C3 1.435(4) . ? C2 C11 1.446(4) . ? C3 C4 1.355(4) . ? C3 H3 0.9500 . ? C4 C9 1.436(4) . ? C4 C5 1.509(4) . ? C5 C6 1.530(4) . ? C5 C13 1.535(5) . ? C5 H5 1.0000 . ? C6 C7 1.414(4) . ? C6 H6 0.9500 . ? C7 C8 1.537(4) . ? C7 H7 0.9500 . ? C8 C9 1.501(4) . ? C8 C14 1.547(4) . ? C8 H8 1.0000 . ? C9 C10 1.360(4) . ? C10 C11 1.432(4) . ? C10 H10 0.9500 . ? C11 C12 1.408(3) . ? C12 C11 1.408(3) 2_655 ? C12 C15 1.498(5) . ? C13 C14 1.475(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.413(3) . ? C15 C16 1.413(3) 2_655 ? C16 C17 1.426(4) . ? C16 C25 1.443(4) . ? C17 C18 1.358(4) . ? C17 H17 0.9500 . ? C18 C23 1.420(4) . ? C18 C19 1.515(4) . ? C19 C20 1.531(5) . ? C19 C27 1.540(4) . ? C19 H19 1.0000 . ? C20 C21 1.424(5) . ? C20 H20 0.9500 . ? C21 C22 1.537(5) . ? C21 H21 0.9500 . ? C22 C23 1.514(4) . ? C22 C28 1.525(5) . ? C22 H22 1.0000 . ? C23 C24 1.369(4) . ? C24 C25 1.436(4) . ? C24 H24 0.9500 . ? C25 C26 1.403(3) . ? C26 C25 1.403(3) 2_655 ? C26 C37 1.506(5) . ? C27 C28 1.451(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.377(4) 2_655 ? C29 C30 1.377(4) . ? C29 H29 0.9500 . ? C30 C31 1.388(4) . ? C30 C33 1.507(5) . ? C31 C32 1.397(3) . ? C31 H31 0.9500 . ? C32 C31 1.397(3) 2_655 ? C34 C35 1.380(5) . ? C34 C35 1.380(5) 2_655 ? C34 H34 0.9500 . ? C35 C36 1.396(4) . ? C35 C38 1.497(6) . ? C36 C37 1.390(4) . ? C36 H36 0.9500 . ? C37 C36 1.390(4) 2_655 ? C39 H39 1.0000 . ? C40 H40 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 120.3(3) . 2_655 ? C2 C1 C32 119.87(16) . . ? C2 C1 C32 119.87(16) 2_655 . ? C1 C2 C3 122.3(2) . . ? C1 C2 C11 119.8(2) . . ? C3 C2 C11 117.9(2) . . ? C4 C3 C2 121.3(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C9 120.9(3) . . ? C3 C4 C5 126.7(2) . . ? C9 C4 C5 112.4(2) . . ? C4 C5 C6 107.7(2) . . ? C4 C5 C13 106.7(2) . . ? C6 C5 C13 106.5(3) . . ? C4 C5 H5 111.9 . . ? C6 C5 H5 111.9 . . ? C13 C5 H5 111.9 . . ? C7 C6 C5 112.2(3) . . ? C7 C6 H6 123.9 . . ? C5 C6 H6 123.9 . . ? C6 C7 C8 112.7(3) . . ? C6 C7 H7 123.7 . . ? C8 C7 H7 123.7 . . ? C9 C8 C7 107.9(2) . . ? C9 C8 C14 106.5(2) . . ? C7 C8 C14 105.7(2) . . ? C9 C8 H8 112.1 . . ? C7 C8 H8 112.1 . . ? C14 C8 H8 112.1 . . ? C10 C9 C4 119.7(3) . . ? C10 C9 C8 127.8(3) . . ? C4 C9 C8 112.5(2) . . ? C9 C10 C11 121.4(2) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C12 C11 C10 121.4(2) . . ? C12 C11 C2 119.8(2) . . ? C10 C11 C2 118.8(2) . . ? C11 C12 C11 120.5(3) 2_655 . ? C11 C12 C15 119.77(16) 2_655 . ? C11 C12 C15 119.77(16) . . ? C14 C13 C5 111.1(3) . . ? C14 C13 H13A 109.4 . . ? C5 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C5 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C13 C14 C8 111.1(3) . . ? C13 C14 H14A 109.4 . . ? C8 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? C8 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C16 120.4(3) . 2_655 ? C16 C15 C12 119.81(16) . . ? C16 C15 C12 119.81(16) 2_655 . ? C15 C16 C17 121.7(2) . . ? C15 C16 C25 119.6(2) . . ? C17 C16 C25 118.7(2) . . ? C18 C17 C16 121.0(2) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C23 120.8(3) . . ? C17 C18 C19 127.2(3) . . ? C23 C18 C19 112.0(2) . . ? C18 C19 C20 108.0(2) . . ? C18 C19 C27 106.1(2) . . ? C20 C19 C27 106.3(2) . . ? C18 C19 H19 112.0 . . ? C20 C19 H19 112.0 . . ? C27 C19 H19 112.0 . . ? C21 C20 C19 112.1(3) . . ? C21 C20 H20 123.9 . . ? C19 C20 H20 123.9 . . ? C20 C21 C22 112.1(3) . . ? C20 C21 H21 123.9 . . ? C22 C21 H21 123.9 . . ? C23 C22 C28 106.3(3) . . ? C23 C22 C21 107.4(2) . . ? C28 C22 C21 106.4(3) . . ? C23 C22 H22 112.1 . . ? C28 C22 H22 112.1 . . ? C21 C22 H22 112.1 . . ? C24 C23 C18 120.6(3) . . ? C24 C23 C22 126.4(3) . . ? C18 C23 C22 113.1(2) . . ? C23 C24 C25 120.5(2) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C26 C25 C24 122.0(2) . . ? C26 C25 C16 119.6(2) . . ? C24 C25 C16 118.4(2) . . ? C25 C26 C25 121.1(3) 2_655 . ? C25 C26 C37 119.44(16) 2_655 . ? C25 C26 C37 119.44(16) . . ? C28 C27 C19 111.5(3) . . ? C28 C27 H27A 109.3 . . ? C19 C27 H27A 109.3 . . ? C28 C27 H27B 109.3 . . ? C19 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? C27 C28 C22 111.7(3) . . ? C27 C28 H28A 109.3 . . ? C22 C28 H28A 109.3 . . ? C27 C28 H28B 109.3 . . ? C22 C28 H28B 109.3 . . ? H28A C28 H28B 108.0 . . ? C30 C29 C30 119.2(4) 2_655 . ? C30 C29 H29 120.4 2_655 . ? C30 C29 H29 120.4 . . ? C29 C30 C31 120.8(3) . . ? C29 C30 C33 121.1(3) . . ? C31 C30 C33 118.1(3) . . ? C30 C31 C32 120.7(3) . . ? C30 C31 H31 119.6 . . ? C32 C31 H31 119.6 . . ? C31 C32 C31 117.9(4) . 2_655 ? C31 C32 C1 121.07(18) . . ? C31 C32 C1 121.07(18) 2_655 . ? F9 C33 F7 104.6(14) . . ? F9 C33 F3 92.3(16) . . ? F7 C33 F3 124.2(14) . . ? F9 C33 F2 121.7(19) . . ? F7 C33 F2 27(2) . . ? F3 C33 F2 101(2) . . ? F9 C33 F1 21.1(14) . . ? F7 C33 F1 87.1(16) . . ? F3 C33 F1 112.1(19) . . ? F2 C33 F1 108.8(17) . . ? F9 C33 F8 104.8(16) . . ? F7 C33 F8 107.5(16) . . ? F3 C33 F8 18(2) . . ? F2 C33 F8 82.9(16) . . ? F1 C33 F8 122.1(16) . . ? F9 C33 C30 113.2(6) . . ? F7 C33 C30 110.7(13) . . ? F3 C33 C30 110.2(10) . . ? F2 C33 C30 114.6(16) . . ? F1 C33 C30 110.1(8) . . ? F8 C33 C30 115.4(12) . . ? C35 C34 C35 119.8(4) . 2_655 ? C35 C34 H34 120.1 . . ? C35 C34 H34 120.1 2_655 . ? C34 C35 C36 120.5(3) . . ? C34 C35 C38 120.9(3) . . ? C36 C35 C38 118.6(4) . . ? C37 C36 C35 119.7(3) . . ? C37 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C36 C37 C36 119.8(4) . 2_655 ? C36 C37 C26 120.08(19) . . ? C36 C37 C26 120.08(19) 2_655 . ? F6 C38 F10 77.0(11) . . ? F6 C38 F5 111.9(10) . . ? F10 C38 F5 118(2) . . ? F6 C38 F4 98.5(14) . . ? F10 C38 F4 28(2) . . ? F5 C38 F4 93.2(11) . . ? F6 C38 F11 27.6(8) . . ? F10 C38 F11 104.3(11) . . ? F5 C38 F11 102.0(9) . . ? F4 C38 F11 125.7(14) . . ? F6 C38 C35 121.1(12) . . ? F10 C38 C35 111.7(8) . . ? F5 C38 C35 113.1(3) . . ? F4 C38 C35 114.6(9) . . ? F11 C38 C35 106.5(10) . . ? Cl7 C39 Cl9 115.1(5) . . ? Cl7 C39 Cl2 114.2(4) . . ? Cl9 C39 Cl2 112.4(7) . . ? Cl7 C39 Cl8 107.1(5) . . ? Cl9 C39 Cl8 103.2(7) . . ? Cl2 C39 Cl8 18.3(6) . . ? Cl7 C39 Cl1 7.9(6) . . ? Cl9 C39 Cl1 122.3(7) . . ? Cl2 C39 Cl1 111.3(3) . . ? Cl8 C39 Cl1 106.7(4) . . ? Cl7 C39 Cl3 100.9(5) . . ? Cl9 C39 Cl3 14.5(7) . . ? Cl2 C39 Cl3 119.0(6) . . ? Cl8 C39 Cl3 106.1(8) . . ? Cl1 C39 Cl3 108.3(4) . . ? Cl7 C39 H39 111.0 . . ? Cl9 C39 H39 96.6 . . ? Cl2 C39 H39 105.8 . . ? Cl8 C39 H39 123.6 . . ? Cl1 C39 H39 105.8 . . ? Cl3 C39 H39 105.8 . . ? Cl12 C40 Cl11 117.9(7) . . ? Cl12 C40 Cl6 115.1(5) . . ? Cl11 C40 Cl6 70.0(5) . . ? Cl12 C40 Cl4 93.9(5) . . ? Cl11 C40 Cl4 40.1(5) . . ? Cl6 C40 Cl4 109.3(3) . . ? Cl12 C40 Cl5 14.9(4) . . ? Cl11 C40 Cl5 132.3(5) . . ? Cl6 C40 Cl5 113.3(2) . . ? Cl4 C40 Cl5 107.9(2) . . ? Cl12 C40 Cl10 110.4(5) . . ? Cl11 C40 Cl10 101.0(6) . . ? Cl6 C40 Cl10 33.2(2) . . ? Cl4 C40 Cl10 141.2(4) . . ? Cl5 C40 Cl10 100.6(3) . . ? Cl12 C40 H40 119.6 . . ? Cl11 C40 H40 114.9 . . ? Cl6 C40 H40 108.8 . . ? Cl4 C40 H40 108.8 . . ? Cl5 C40 H40 108.8 . . ? Cl10 C40 H40 85.6 . . ? 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 C2 C1 C2 C3 -177.0(3) 2_655 . . . ? C32 C1 C2 C3 3.0(3) . . . . ? C2 C1 C2 C11 0.17(16) 2_655 . . . ? C32 C1 C2 C11 -179.83(16) . . . . ? C1 C2 C3 C4 177.8(2) . . . . ? C11 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 C9 0.9(4) . . . . ? C2 C3 C4 C5 -176.7(3) . . . . ? C3 C4 C5 C6 -125.6(3) . . . . ? C9 C4 C5 C6 56.6(3) . . . . ? C3 C4 C5 C13 120.4(3) . . . . ? C9 C4 C5 C13 -57.4(3) . . . . ? C4 C5 C6 C7 -55.3(3) . . . . ? C13 C5 C6 C7 58.8(3) . . . . ? C5 C6 C7 C8 -0.6(4) . . . . ? C6 C7 C8 C9 55.8(3) . . . . ? C6 C7 C8 C14 -57.9(3) . . . . ? C3 C4 C9 C10 -1.4(4) . . . . ? C5 C4 C9 C10 176.5(2) . . . . ? C3 C4 C9 C8 -179.3(2) . . . . ? C5 C4 C9 C8 -1.4(3) . . . . ? C7 C8 C9 C10 127.9(3) . . . . ? C14 C8 C9 C10 -119.0(3) . . . . ? C7 C8 C9 C4 -54.4(3) . . . . ? C14 C8 C9 C4 58.7(3) . . . . ? C4 C9 C10 C11 0.4(4) . . . . ? C8 C9 C10 C11 178.0(3) . . . . ? C9 C10 C11 C12 -177.4(2) . . . . ? C9 C10 C11 C2 1.0(4) . . . . ? C1 C2 C11 C12 -0.3(3) . . . . ? C3 C2 C11 C12 177.0(2) . . . . ? C1 C2 C11 C10 -178.8(2) . . . . ? C3 C2 C11 C10 -1.5(4) . . . . ? C10 C11 C12 C11 178.6(3) . . . 2_655 ? C2 C11 C12 C11 0.17(16) . . . 2_655 ? C10 C11 C12 C15 -1.4(3) . . . . ? C2 C11 C12 C15 -179.83(16) . . . . ? C4 C5 C13 C14 57.8(3) . . . . ? C6 C5 C13 C14 -57.0(3) . . . . ? C5 C13 C14 C8 -1.2(4) . . . . ? C9 C8 C14 C13 -56.6(3) . . . . ? C7 C8 C14 C13 58.0(3) . . . . ? C11 C12 C15 C16 88.29(17) 2_655 . . . ? C11 C12 C15 C16 -91.71(17) . . . . ? C11 C12 C15 C16 -91.71(17) 2_655 . . 2_655 ? C11 C12 C15 C16 88.29(17) . . . 2_655 ? C16 C15 C16 C17 -179.5(3) 2_655 . . . ? C12 C15 C16 C17 0.5(3) . . . . ? C16 C15 C16 C25 -0.45(17) 2_655 . . . ? C12 C15 C16 C25 179.55(17) . . . . ? C15 C16 C17 C18 178.3(2) . . . . ? C25 C16 C17 C18 -0.8(4) . . . . ? C16 C17 C18 C23 0.3(4) . . . . ? C16 C17 C18 C19 -176.8(3) . . . . ? C17 C18 C19 C20 -126.7(3) . . . . ? C23 C18 C19 C20 56.0(3) . . . . ? C17 C18 C19 C27 119.7(3) . . . . ? C23 C18 C19 C27 -57.6(3) . . . . ? C18 C19 C20 C21 -55.7(3) . . . . ? C27 C19 C20 C21 57.7(3) . . . . ? C19 C20 C21 C22 -0.3(4) . . . . ? C20 C21 C22 C23 55.7(3) . . . . ? C20 C21 C22 C28 -57.8(3) . . . . ? C17 C18 C23 C24 0.6(4) . . . . ? C19 C18 C23 C24 178.1(3) . . . . ? C17 C18 C23 C22 -177.4(3) . . . . ? C19 C18 C23 C22 0.1(3) . . . . ? C28 C22 C23 C24 -120.1(3) . . . . ? C21 C22 C23 C24 126.3(3) . . . . ? C28 C22 C23 C18 57.7(3) . . . . ? C21 C22 C23 C18 -55.9(3) . . . . ? C18 C23 C24 C25 -0.9(4) . . . . ? C22 C23 C24 C25 176.7(3) . . . . ? C23 C24 C25 C26 -179.1(2) . . . . ? C23 C24 C25 C16 0.4(4) . . . . ? C15 C16 C25 C26 0.9(3) . . . . ? C17 C16 C25 C26 180.0(2) . . . . ? C15 C16 C25 C24 -178.7(2) . . . . ? C17 C16 C25 C24 0.4(4) . . . . ? C24 C25 C26 C25 179.1(3) . . . 2_655 ? C16 C25 C26 C25 -0.45(17) . . . 2_655 ? C24 C25 C26 C37 -0.9(3) . . . . ? C16 C25 C26 C37 179.55(17) . . . . ? C18 C19 C27 C28 57.5(3) . . . . ? C20 C19 C27 C28 -57.3(3) . . . . ? C19 C27 C28 C22 -0.3(4) . . . . ? C23 C22 C28 C27 -56.6(3) . . . . ? C21 C22 C28 C27 57.6(3) . . . . ? C30 C29 C30 C31 0.1(2) 2_655 . . . ? C30 C29 C30 C33 -179.4(4) 2_655 . . . ? C29 C30 C31 C32 -0.3(4) . . . . ? C33 C30 C31 C32 179.3(3) . . . . ? C30 C31 C32 C31 0.1(2) . . . 2_655 ? C30 C31 C32 C1 -179.9(2) . . . . ? C2 C1 C32 C31 -119.37(19) . . . . ? C2 C1 C32 C31 60.63(19) 2_655 . . . ? C2 C1 C32 C31 60.63(19) . . . 2_655 ? C2 C1 C32 C31 -119.37(19) 2_655 . . 2_655 ? C29 C30 C33 F9 121.8(12) . . . . ? C31 C30 C33 F9 -57.8(12) . . . . ? C29 C30 C33 F7 4.8(16) . . . . ? C31 C30 C33 F7 -174.8(15) . . . . ? C29 C30 C33 F3 -136.4(13) . . . . ? C31 C30 C33 F3 44.1(14) . . . . ? C29 C30 C33 F2 -24(3) . . . . ? C31 C30 C33 F2 157(3) . . . . ? C29 C30 C33 F1 99.4(18) . . . . ? C31 C30 C33 F1 -80.2(18) . . . . ? C29 C30 C33 F8 -117(2) . . . . ? C31 C30 C33 F8 63(2) . . . . ? C35 C34 C35 C36 0.6(2) 2_655 . . . ? C35 C34 C35 C38 178.5(4) 2_655 . . . ? C34 C35 C36 C37 -1.2(4) . . . . ? C38 C35 C36 C37 -179.1(3) . . . . ? C35 C36 C37 C36 0.6(2) . . . 2_655 ? C35 C36 C37 C26 -179.4(2) . . . . ? C25 C26 C37 C36 -83.82(19) 2_655 . . . ? C25 C26 C37 C36 96.18(19) . . . . ? C25 C26 C37 C36 96.18(19) 2_655 . . 2_655 ? C25 C26 C37 C36 -83.82(19) . . . 2_655 ? C34 C35 C38 F6 55.1(17) . . . . ? C36 C35 C38 F6 -127.0(17) . . . . ? C34 C35 C38 F10 143(3) . . . . ? C36 C35 C38 F10 -40(3) . . . . ? C34 C35 C38 F5 -81.9(5) . . . . ? C36 C35 C38 F5 96.0(5) . . . . ? C34 C35 C38 F4 172.9(11) . . . . ? C36 C35 C38 F4 -9.2(12) . . . . ? C34 C35 C38 F11 29.4(14) . . . . ? C36 C35 C38 F11 -152.7(14) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.103 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 923854' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl6 #TrackingRef '8cBPH.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H42, C4 H10 O' _chemical_formula_sum 'C56 H52 O' _chemical_formula_weight 740.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 11.1984(5) _cell_length_b 11.3073(5) _cell_length_c 16.8154(7) _cell_angle_alpha 73.8090(10) _cell_angle_beta 86.8410(10) _cell_angle_gamma 75.5040(10) _cell_volume 1979.44(15) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 8014 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9872 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details ; 'ABSCOR (Rigaku, 1995)' ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19899 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.49 _reflns_number_total 9054 _reflns_number_gt 6560 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1500P)^2^+0.5251P] 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 9054 _refine_ls_number_parameters 558 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0902 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.2343 _refine_ls_wR_factor_gt 0.2024 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0192(8) 0.4840(12) 1.0045(11) 0.0475(17) Uani 0.50 1 d P A -1 C53 C 0.0511(9) 0.6351(10) 1.0697(6) 0.096(3) Uiso 0.50 1 d P A -1 H53 H 0.0503 0.5691 1.1217 0.145 Uiso 0.50 1 calc PR A -1 H54 H 0.0153 0.7188 1.0786 0.145 Uiso 0.50 1 calc PR A -1 H55 H 0.1363 0.6302 1.0512 0.145 Uiso 0.50 1 calc PR A -1 C54 C -0.0467(5) 0.4534(5) 0.9501(3) 0.0472(11) Uani 0.50 1 d P A -1 H56 H -0.0372 0.5047 0.8929 0.057 Uiso 0.50 1 calc PR A -1 H57 H -0.1353 0.4719 0.9637 0.057 Uiso 0.50 1 calc PR A -1 C55 C -0.0230(6) 0.6157(5) 1.0051(4) 0.0597(15) Uani 0.50 1 d P A -1 H58 H -0.1118 0.6356 1.0183 0.072 Uiso 0.50 1 calc PR A -1 H59 H -0.0112 0.6722 0.9502 0.072 Uiso 0.50 1 calc PR A -1 C56 C 0.0006(6) 0.3152(5) 0.9562(3) 0.0500(13) Uani 0.50 1 d P A -1 H60 H 0.0903 0.2955 0.9498 0.075 Uiso 0.50 1 calc PR A -1 H61 H -0.0376 0.2947 0.9123 0.075 Uiso 0.50 1 calc PR A -1 H62 H -0.0200 0.2648 1.0103 0.075 Uiso 0.50 1 calc PR A -1 C1 C 0.10342(17) -0.01686(17) 0.89433(11) 0.0264(4) Uani 1 1 d . . . H1 H 0.0719 -0.0715 0.9396 0.032 Uiso 1 1 calc R . . C2 C 0.23093(16) -0.03784(16) 0.88360(10) 0.0236(4) Uani 1 1 d . . . C3 C 0.31517(17) -0.13830(16) 0.94072(11) 0.0262(4) Uani 1 1 d . . . H3 H 0.2839 -0.1929 0.9861 0.031 Uiso 1 1 calc R . . C4 C 0.43885(17) -0.15644(16) 0.93080(11) 0.0262(4) Uani 1 1 d . . . C5 C 0.53840(18) -0.25621(18) 0.98623(12) 0.0328(4) Uani 1 1 d . . . H5 H 0.5033 -0.3142 1.0325 0.039 Uiso 1 1 calc R . . C6 C 0.62281(19) -0.32836(18) 0.93183(13) 0.0359(5) Uani 1 1 d . . . H6 H 0.6405 -0.4179 0.9415 0.043 Uiso 1 1 calc R . . C7 C 0.67168(19) -0.24732(19) 0.86553(12) 0.0339(4) Uani 1 1 d . . . H7 H 0.7262 -0.2764 0.8259 0.041 Uiso 1 1 calc R . . C8 C 0.62696(17) -0.10727(18) 0.86460(12) 0.0322(4) Uani 1 1 d . . . H8 H 0.6612 -0.0503 0.8173 0.039 Uiso 1 1 calc R . . C9 C 0.48752(16) -0.07475(16) 0.86270(11) 0.0254(4) Uani 1 1 d . . . C10 C 0.41097(16) 0.02033(16) 0.80625(11) 0.0243(4) Uani 1 1 d . . . H10 H 0.4449 0.0723 0.7608 0.029 Uiso 1 1 calc R . . C11 C 0.27945(16) 0.04311(16) 0.81448(10) 0.0225(4) Uani 1 1 d . . . C12 C 0.19726(16) 0.14287(16) 0.75834(10) 0.0225(4) Uani 1 1 d . . . C13 C 0.06884(16) 0.16465(16) 0.77094(10) 0.0238(4) Uani 1 1 d . . . C14 C -0.01705(16) 0.26961(17) 0.71825(11) 0.0259(4) Uani 1 1 d . . . H14 H 0.0120 0.3240 0.6716 0.031 Uiso 1 1 calc R . . C15 C -0.13985(16) 0.29213(17) 0.73439(11) 0.0276(4) Uani 1 1 d . . . C16 C -0.24010(17) 0.40216(19) 0.68664(13) 0.0338(4) Uani 1 1 d . . . H16 H -0.2068 0.4584 0.6384 0.041 Uiso 1 1 calc R . . C17 C -0.3024(2) 0.4736(2) 0.74921(15) 0.0452(6) Uani 1 1 d . . . H17 H -0.3091 0.5612 0.7428 0.054 Uiso 1 1 calc R . . C18 C -0.3496(2) 0.3917(2) 0.81900(16) 0.0506(6) Uani 1 1 d . . . H18 H -0.3910 0.4189 0.8640 0.061 Uiso 1 1 calc R . . C19 C -0.32506(18) 0.2555(2) 0.81173(14) 0.0394(5) Uani 1 1 d . . . H19 H -0.3577 0.1984 0.8599 0.047 Uiso 1 1 calc R . . C20 C -0.18679(17) 0.21049(18) 0.80337(12) 0.0298(4) Uani 1 1 d . . . C21 C -0.10909(17) 0.10827(17) 0.85378(11) 0.0284(4) Uani 1 1 d . . . H21 H -0.1414 0.0533 0.8984 0.034 Uiso 1 1 calc R . . C22 C 0.02157(17) 0.08245(17) 0.84014(11) 0.0253(4) Uani 1 1 d . . . C23 C -0.3844(2) 0.2656(2) 0.73029(16) 0.0486(6) Uani 1 1 d . . . H23A H -0.3697 0.1797 0.7222 0.058 Uiso 1 1 calc R . . H23B H -0.4747 0.2993 0.7330 0.058 Uiso 1 1 calc R . . C24 C -0.3371(2) 0.3469(2) 0.66034(15) 0.0438(5) Uani 1 1 d . . . H24A H -0.4059 0.4170 0.6314 0.053 Uiso 1 1 calc R . . H24B H -0.3003 0.2975 0.6210 0.053 Uiso 1 1 calc R . . C25 C 0.61640(19) -0.1836(2) 1.01842(12) 0.0362(5) Uani 1 1 d . . . H25A H 0.5645 -0.1328 1.0527 0.043 Uiso 1 1 calc R . . H25B H 0.6851 -0.2451 1.0537 0.043 Uiso 1 1 calc R . . C26 C 0.66603(19) -0.0997(2) 0.94945(14) 0.0375(5) Uani 1 1 d . . . H26A H 0.7572 -0.1232 0.9540 0.045 Uiso 1 1 calc R . . H26B H 0.6367 -0.0111 0.9529 0.045 Uiso 1 1 calc R . . C27 C 0.24627(15) 0.22871(16) 0.68587(10) 0.0227(4) Uani 1 1 d . . . C28 C 0.26820(15) 0.34272(16) 0.69308(11) 0.0235(4) Uani 1 1 d . . . C29 C 0.23919(17) 0.38477(17) 0.76635(11) 0.0270(4) Uani 1 1 d . . . H29 H 0.2091 0.3321 0.8134 0.032 Uiso 1 1 calc R . . C30 C 0.25424(18) 0.49942(18) 0.76942(12) 0.0305(4) Uani 1 1 d . . . C31 C 0.2203(2) 0.5600(2) 0.83978(13) 0.0423(5) Uani 1 1 d . . . H31 H 0.1892 0.5029 0.8887 0.051 Uiso 1 1 calc R . . C32 C 0.1228(2) 0.6859(2) 0.80426(16) 0.0467(6) Uani 1 1 d . . . H32A H 0.0482 0.6670 0.7869 0.056 Uiso 1 1 calc R . . H32B H 0.0988 0.7302 0.8480 0.056 Uiso 1 1 calc R . . C33 C 0.1707(2) 0.7696(2) 0.73271(15) 0.0439(5) Uani 1 1 d . . . H33A H 0.1687 0.8511 0.7446 0.053 Uiso 1 1 calc R . . H33B H 0.1177 0.7881 0.6834 0.053 Uiso 1 1 calc R . . C34 C 0.3050(2) 0.7055(2) 0.71455(13) 0.0409(5) Uani 1 1 d . . . H34 H 0.3396 0.7606 0.6664 0.049 Uiso 1 1 calc R . . C35 C 0.30170(19) 0.58005(18) 0.69978(12) 0.0324(4) Uani 1 1 d . . . C36 C 0.33355(17) 0.54212(18) 0.63033(12) 0.0297(4) Uani 1 1 d . . . H36 H 0.3676 0.5948 0.5853 0.036 Uiso 1 1 calc R . . C37 C 0.31674(15) 0.42417(17) 0.62371(11) 0.0257(4) Uani 1 1 d . . . C38 C 0.34089(16) 0.38826(18) 0.55070(11) 0.0278(4) Uani 1 1 d . . . H38 H 0.3763 0.4399 0.5060 0.033 Uiso 1 1 calc R . . C39 C 0.31478(16) 0.27902(17) 0.54101(11) 0.0255(4) Uani 1 1 d . . . C40 C 0.33249(17) 0.24771(18) 0.46372(11) 0.0295(4) Uani 1 1 d . . . H40 H 0.3654 0.3008 0.4184 0.035 Uiso 1 1 calc R . . C41 C 0.30286(18) 0.14319(18) 0.45435(11) 0.0313(4) Uani 1 1 d . . . C42 C 0.3189(2) 0.0958(2) 0.37785(12) 0.0388(5) Uani 1 1 d . . . H42 H 0.3534 0.1532 0.3309 0.047 Uiso 1 1 calc R . . C43 C 0.1929(2) 0.0818(2) 0.35561(14) 0.0481(6) Uani 1 1 d . . . H43 H 0.1531 0.1219 0.3031 0.058 Uiso 1 1 calc R . . C44 C 0.1434(2) 0.0026(2) 0.42214(13) 0.0427(5) Uani 1 1 d . . . H44 H 0.0658 -0.0162 0.4195 0.051 Uiso 1 1 calc R . . C45 C 0.2279(2) -0.0503(2) 0.49944(12) 0.0352(4) Uani 1 1 d . . . H45 H 0.1918 -0.1062 0.5463 0.042 Uiso 1 1 calc R . . C46 C 0.25302(17) 0.06187(18) 0.52211(11) 0.0294(4) Uani 1 1 d . . . C47 C 0.23650(16) 0.08717(17) 0.59729(11) 0.0269(4) Uani 1 1 d . . . H47 H 0.2053 0.0312 0.6419 0.032 Uiso 1 1 calc R . . C48 C 0.26560(15) 0.19688(16) 0.60975(10) 0.0233(4) Uani 1 1 d . . . C49 C 0.3515(2) -0.1210(2) 0.47211(14) 0.0428(5) Uani 1 1 d . . . H49A H 0.4106 -0.1541 0.5194 0.051 Uiso 1 1 calc R . . H49B H 0.3396 -0.1943 0.4550 0.051 Uiso 1 1 calc R . . C50 C 0.4027(2) -0.0380(2) 0.40326(13) 0.0416(5) Uani 1 1 d . . . H50A H 0.4137 -0.0741 0.3553 0.050 Uiso 1 1 calc R . . H50B H 0.4848 -0.0340 0.4198 0.050 Uiso 1 1 calc R . . C51 C 0.3329(2) 0.5970(2) 0.86133(13) 0.0425(5) Uani 1 1 d . . . H51 H 0.3687 0.5692 0.9154 0.051 Uiso 1 1 calc R . . C52 C 0.3790(2) 0.6763(2) 0.79362(14) 0.0438(5) Uani 1 1 d . . . H52 H 0.4489 0.7082 0.7969 0.053 Uiso 1 1 calc R . . O2 O -0.0201(3) 0.4776(3) 0.53454(18) 0.0389(7) Uani 0.50 1 d P B -1 C57 C -0.0007(4) 0.6276(5) 0.6050(4) 0.0522(13) Uani 0.50 1 d P B -1 H63 H -0.0857 0.6361 0.6245 0.078 Uiso 0.50 1 calc PR B -1 H64 H 0.0226 0.7079 0.5978 0.078 Uiso 0.50 1 calc PR B -1 H65 H 0.0549 0.5598 0.6459 0.078 Uiso 0.50 1 calc PR B -1 C58 C 0.0085(16) 0.5963(18) 0.5262(10) 0.061(5) Uani 0.50 1 d P B -1 H66 H -0.0490 0.6639 0.4854 0.073 Uiso 0.50 1 calc PR B -1 H67 H 0.0933 0.5925 0.5051 0.073 Uiso 0.50 1 calc PR B -1 C59 C -0.0565(4) 0.3080(5) 0.4888(3) 0.0474(11) Uani 0.50 1 d P B -1 H68 H -0.0071 0.2449 0.5351 0.071 Uiso 0.50 1 calc PR B -1 H69 H -0.0467 0.2751 0.4401 0.071 Uiso 0.50 1 calc PR B -1 H70 H -0.1436 0.3253 0.5041 0.071 Uiso 0.50 1 calc PR B -1 C58A C -0.0138(12) 0.4284(16) 0.4691(6) 0.034(2) Uani 0.50 1 d P B -1 H71 H 0.0725 0.4113 0.4502 0.040 Uiso 0.50 1 calc PR B -1 H72 H -0.0651 0.4921 0.4230 0.040 Uiso 0.50 1 calc PR B -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 O1 0.045(6) 0.047(6) 0.060(4) -0.027(4) 0.011(5) -0.015(3) C54 0.048(3) 0.058(3) 0.053(3) -0.033(3) 0.008(2) -0.025(2) C55 0.082(4) 0.049(3) 0.061(3) -0.026(3) 0.027(3) -0.031(3) C56 0.079(4) 0.041(3) 0.043(3) -0.018(2) 0.017(3) -0.033(3) C1 0.0293(9) 0.0247(8) 0.0246(8) -0.0026(7) 0.0038(7) -0.0111(7) C2 0.0280(9) 0.0220(8) 0.0213(8) -0.0049(7) 0.0018(7) -0.0086(7) C3 0.0317(9) 0.0217(8) 0.0236(8) -0.0022(7) 0.0023(7) -0.0088(7) C4 0.0295(9) 0.0226(8) 0.0245(8) -0.0031(7) -0.0013(7) -0.0063(7) C5 0.0311(9) 0.0278(9) 0.0304(10) 0.0043(8) -0.0012(8) -0.0046(7) C6 0.0375(10) 0.0240(9) 0.0430(11) -0.0081(8) -0.0028(9) -0.0019(8) C7 0.0351(10) 0.0326(10) 0.0286(9) -0.0059(8) 0.0007(8) -0.0013(8) C8 0.0263(9) 0.0292(9) 0.0349(10) 0.0013(8) -0.0005(8) -0.0065(7) C9 0.0270(9) 0.0236(8) 0.0263(9) -0.0062(7) 0.0009(7) -0.0081(7) C10 0.0271(9) 0.0232(8) 0.0230(8) -0.0038(7) 0.0027(7) -0.0102(7) C11 0.0261(8) 0.0213(8) 0.0212(8) -0.0061(7) 0.0018(7) -0.0077(6) C12 0.0261(8) 0.0223(8) 0.0211(8) -0.0055(7) 0.0014(7) -0.0100(7) C13 0.0266(8) 0.0244(8) 0.0221(8) -0.0062(7) 0.0023(7) -0.0098(7) C14 0.0255(8) 0.0274(9) 0.0239(8) -0.0028(7) 0.0016(7) -0.0099(7) C15 0.0260(9) 0.0269(9) 0.0279(9) -0.0029(7) 0.0014(7) -0.0084(7) C16 0.0256(9) 0.0317(10) 0.0362(10) 0.0024(8) 0.0017(8) -0.0064(7) C17 0.0438(12) 0.0312(11) 0.0502(13) -0.0023(10) 0.0126(10) -0.0030(9) C18 0.0446(12) 0.0398(12) 0.0538(14) -0.0038(11) 0.0194(11) 0.0000(10) C19 0.0274(9) 0.0360(11) 0.0446(12) 0.0044(9) 0.0080(9) -0.0084(8) C20 0.0264(9) 0.0297(9) 0.0317(9) -0.0037(8) 0.0044(8) -0.0100(7) C21 0.0285(9) 0.0276(9) 0.0286(9) -0.0027(7) 0.0055(7) -0.0125(7) C22 0.0276(9) 0.0254(9) 0.0245(8) -0.0057(7) 0.0035(7) -0.0112(7) C23 0.0289(10) 0.0523(14) 0.0575(14) 0.0044(11) -0.0064(10) -0.0177(9) C24 0.0333(10) 0.0437(12) 0.0458(12) 0.0039(10) -0.0090(9) -0.0102(9) C25 0.0363(10) 0.0399(11) 0.0280(9) -0.0074(8) -0.0085(8) -0.0016(8) C26 0.0309(10) 0.0336(10) 0.0474(12) -0.0093(9) -0.0100(9) -0.0065(8) C27 0.0186(7) 0.0250(8) 0.0216(8) -0.0013(7) -0.0011(6) -0.0055(6) C28 0.0197(8) 0.0252(8) 0.0226(8) -0.0004(7) -0.0021(6) -0.0063(6) C29 0.0296(9) 0.0267(9) 0.0231(8) -0.0006(7) -0.0006(7) -0.0107(7) C30 0.0370(10) 0.0273(9) 0.0282(9) -0.0047(8) 0.0004(8) -0.0130(8) C31 0.0670(15) 0.0320(11) 0.0344(11) -0.0107(9) 0.0083(10) -0.0236(10) C32 0.0530(13) 0.0393(12) 0.0531(14) -0.0188(11) 0.0099(11) -0.0159(10) C33 0.0561(14) 0.0275(10) 0.0457(12) -0.0049(9) -0.0068(11) -0.0101(9) C34 0.0577(13) 0.0321(10) 0.0370(11) -0.0049(9) 0.0013(10) -0.0240(10) C35 0.0369(10) 0.0289(9) 0.0313(10) -0.0012(8) -0.0017(8) -0.0153(8) C36 0.0293(9) 0.0287(9) 0.0288(9) 0.0019(7) -0.0010(7) -0.0135(7) C37 0.0200(8) 0.0258(9) 0.0273(9) 0.0011(7) -0.0017(7) -0.0072(6) C38 0.0239(8) 0.0300(9) 0.0249(9) 0.0015(7) 0.0019(7) -0.0087(7) C39 0.0215(8) 0.0269(9) 0.0232(8) -0.0011(7) 0.0007(7) -0.0040(7) C40 0.0298(9) 0.0313(9) 0.0204(8) 0.0005(7) 0.0018(7) -0.0039(7) C41 0.0332(9) 0.0320(10) 0.0240(9) -0.0047(8) 0.0014(8) -0.0031(8) C42 0.0496(12) 0.0405(11) 0.0241(9) -0.0086(8) 0.0041(9) -0.0078(9) C43 0.0519(13) 0.0603(15) 0.0322(11) -0.0184(11) -0.0070(10) -0.0056(11) C44 0.0435(12) 0.0538(14) 0.0352(11) -0.0166(10) -0.0016(9) -0.0144(10) C45 0.0421(11) 0.0375(11) 0.0282(9) -0.0120(8) 0.0036(8) -0.0113(9) C46 0.0308(9) 0.0309(9) 0.0243(9) -0.0061(7) 0.0010(7) -0.0055(7) C47 0.0264(9) 0.0277(9) 0.0248(8) -0.0037(7) 0.0012(7) -0.0071(7) C48 0.0203(8) 0.0247(8) 0.0208(8) -0.0009(7) -0.0005(6) -0.0039(6) C49 0.0475(12) 0.0385(11) 0.0428(12) -0.0176(10) -0.0011(10) -0.0036(9) C50 0.0443(12) 0.0443(12) 0.0353(11) -0.0158(9) 0.0078(9) -0.0053(9) C51 0.0636(15) 0.0325(11) 0.0335(10) -0.0061(9) -0.0118(10) -0.0161(10) C52 0.0553(13) 0.0378(11) 0.0469(12) -0.0140(10) -0.0006(11) -0.0239(10) O2 0.0375(16) 0.0333(16) 0.0471(17) -0.0096(14) -0.0107(14) -0.0096(13) C57 0.036(2) 0.043(2) 0.084(4) -0.031(3) -0.019(2) -0.0011(19) C58 0.043(6) 0.048(7) 0.084(8) 0.003(4) -0.013(4) -0.017(4) C59 0.042(2) 0.045(3) 0.054(3) -0.020(2) -0.023(2) 0.002(2) C58A 0.023(3) 0.047(6) 0.028(3) -0.013(3) -0.003(2) -0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C54 1.371(17) . ? O1 C55 1.449(13) . ? C53 C55 1.496(12) . ? C53 H53 0.9800 . ? C53 H54 0.9800 . ? C53 H55 0.9800 . ? C54 C56 1.495(7) . ? C54 H56 0.9900 . ? C54 H57 0.9900 . ? C55 H58 0.9900 . ? C55 H59 0.9900 . ? C56 H60 0.9800 . ? C56 H61 0.9800 . ? C56 H62 0.9800 . ? C1 C22 1.392(3) . ? C1 C2 1.398(2) . ? C1 H1 0.9500 . ? C2 C3 1.434(2) . ? C2 C11 1.439(2) . ? C3 C4 1.356(3) . ? C3 H3 0.9500 . ? C4 C9 1.434(2) . ? C4 C5 1.511(2) . ? C5 C6 1.527(3) . ? C5 C25 1.546(3) . ? C5 H5 1.0000 . ? C6 C7 1.413(3) . ? C6 H6 0.9500 . ? C7 C8 1.533(3) . ? C7 H7 0.9500 . ? C8 C9 1.512(2) . ? C8 C26 1.546(3) . ? C8 H8 1.0000 . ? C9 C10 1.360(2) . ? C10 C11 1.436(2) . ? C10 H10 0.9500 . ? C11 C12 1.412(2) . ? C12 C13 1.411(2) . ? C12 C27 1.504(2) . ? C13 C14 1.433(2) . ? C13 C22 1.440(2) . ? C14 C15 1.361(2) . ? C14 H14 0.9500 . ? C15 C20 1.433(2) . ? C15 C16 1.515(3) . ? C16 C24 1.521(3) . ? C16 C17 1.535(3) . ? C16 H16 1.0000 . ? C17 C18 1.444(3) . ? C17 H17 0.9500 . ? C18 C19 1.534(3) . ? C18 H18 0.9500 . ? C19 C20 1.516(3) . ? C19 C23 1.519(3) . ? C19 H19 1.0000 . ? C20 C21 1.358(3) . ? C21 C22 1.437(2) . ? C21 H21 0.9500 . ? C23 C24 1.443(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.461(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.409(2) . ? C27 C48 1.415(2) . ? C28 C29 1.434(3) . ? C28 C37 1.444(2) . ? C29 C30 1.364(3) . ? C29 H29 0.9500 . ? C30 C35 1.436(3) . ? C30 C31 1.512(3) . ? C31 C51 1.515(3) . ? C31 C32 1.547(3) . ? C31 H31 1.0000 . ? C32 C33 1.477(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.551(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.516(3) . ? C34 C52 1.518(3) . ? C34 H34 1.0000 . ? C35 C36 1.354(3) . ? C36 C37 1.427(3) . ? C36 H36 0.9500 . ? C37 C38 1.390(3) . ? C38 C39 1.391(3) . ? C38 H38 0.9500 . ? C39 C40 1.431(3) . ? C39 C48 1.445(2) . ? C40 C41 1.356(3) . ? C40 H40 0.9500 . ? C41 C46 1.434(3) . ? C41 C42 1.511(3) . ? C42 C50 1.525(3) . ? C42 C43 1.536(3) . ? C42 H42 1.0000 . ? C43 C44 1.408(3) . ? C43 H43 0.9500 . ? C44 C45 1.537(3) . ? C44 H44 0.9500 . ? C45 C46 1.514(3) . ? C45 C49 1.531(3) . ? C45 H45 1.0000 . ? C46 C47 1.365(3) . ? C47 C48 1.430(2) . ? C47 H47 0.9500 . ? C49 C50 1.463(3) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 C52 1.402(3) . ? C51 H51 0.9500 . ? C52 H52 0.9500 . ? O2 C58A 1.355(11) . ? O2 C58 1.42(2) . ? C57 C58 1.457(16) . ? C57 H63 0.9800 . ? C57 H64 0.9800 . ? C57 H65 0.9800 . ? C58 H66 0.9900 . ? C58 H67 0.9900 . ? C59 C58A 1.499(17) . ? C59 H68 0.9800 . ? C59 H69 0.9800 . ? C59 H70 0.9800 . ? C58A H71 0.9900 . ? C58A H72 0.9900 . ? 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 C54 O1 C55 112.7(7) . . ? O1 C54 C56 108.7(6) . . ? O1 C54 H56 109.9 . . ? C56 C54 H56 109.9 . . ? O1 C54 H57 109.9 . . ? C56 C54 H57 109.9 . . ? H56 C54 H57 108.3 . . ? O1 C55 C53 107.5(9) . . ? O1 C55 H58 110.2 . . ? C53 C55 H58 110.2 . . ? O1 C55 H59 110.2 . . ? C53 C55 H59 110.2 . . ? H58 C55 H59 108.5 . . ? C22 C1 C2 121.41(16) . . ? C22 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C1 C2 C3 121.28(16) . . ? C1 C2 C11 119.73(16) . . ? C3 C2 C11 118.98(15) . . ? C4 C3 C2 120.93(16) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C9 120.22(16) . . ? C3 C4 C5 126.95(16) . . ? C9 C4 C5 112.82(15) . . ? C4 C5 C6 107.54(16) . . ? C4 C5 C25 106.30(15) . . ? C6 C5 C25 106.55(16) . . ? C4 C5 H5 112.0 . . ? C6 C5 H5 112.0 . . ? C25 C5 H5 112.0 . . ? C7 C6 C5 112.59(16) . . ? C7 C6 H6 123.7 . . ? C5 C6 H6 123.7 . . ? C6 C7 C8 112.56(16) . . ? C6 C7 H7 123.7 . . ? C8 C7 H7 123.7 . . ? C9 C8 C7 107.22(16) . . ? C9 C8 C26 106.62(15) . . ? C7 C8 C26 105.85(16) . . ? C9 C8 H8 112.2 . . ? C7 C8 H8 112.2 . . ? C26 C8 H8 112.2 . . ? C10 C9 C4 120.82(16) . . ? C10 C9 C8 127.12(16) . . ? C4 C9 C8 112.05(15) . . ? C9 C10 C11 120.80(16) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 122.38(15) . . ? C12 C11 C2 119.37(15) . . ? C10 C11 C2 118.24(15) . . ? C13 C12 C11 120.28(15) . . ? C13 C12 C27 119.57(15) . . ? C11 C12 C27 120.14(15) . . ? C12 C13 C14 121.91(15) . . ? C12 C13 C22 119.72(16) . . ? C14 C13 C22 118.33(15) . . ? C15 C14 C13 120.64(16) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C20 120.99(17) . . ? C14 C15 C16 126.42(16) . . ? C20 C15 C16 112.57(15) . . ? C15 C16 C24 107.57(16) . . ? C15 C16 C17 106.20(17) . . ? C24 C16 C17 106.23(18) . . ? C15 C16 H16 112.1 . . ? C24 C16 H16 112.1 . . ? C17 C16 H16 112.1 . . ? C18 C17 C16 111.90(19) . . ? C18 C17 H17 124.1 . . ? C16 C17 H17 124.1 . . ? C17 C18 C19 111.9(2) . . ? C17 C18 H18 124.0 . . ? C19 C18 H18 124.0 . . ? C20 C19 C23 107.39(18) . . ? C20 C19 C18 106.48(17) . . ? C23 C19 C18 105.98(19) . . ? C20 C19 H19 112.2 . . ? C23 C19 H19 112.2 . . ? C18 C19 H19 112.2 . . ? C21 C20 C15 120.35(16) . . ? C21 C20 C19 127.33(17) . . ? C15 C20 C19 112.29(16) . . ? C20 C21 C22 120.55(16) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C1 C22 C21 121.37(16) . . ? C1 C22 C13 119.47(16) . . ? C21 C22 C13 119.11(16) . . ? C24 C23 C19 112.53(18) . . ? C24 C23 H23A 109.1 . . ? C19 C23 H23A 109.1 . . ? C24 C23 H23B 109.1 . . ? C19 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? C23 C24 C16 111.79(19) . . ? C23 C24 H24A 109.3 . . ? C16 C24 H24A 109.3 . . ? C23 C24 H24B 109.3 . . ? C16 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? C26 C25 C5 110.66(16) . . ? C26 C25 H25A 109.5 . . ? C5 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? C5 C25 H25B 109.5 . . ? H25A C25 H25B 108.1 . . ? C25 C26 C8 112.08(16) . . ? C25 C26 H26A 109.2 . . ? C8 C26 H26A 109.2 . . ? C25 C26 H26B 109.2 . . ? C8 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C28 C27 C48 120.31(15) . . ? C28 C27 C12 119.92(15) . . ? C48 C27 C12 119.73(15) . . ? C27 C28 C29 122.33(15) . . ? C27 C28 C37 119.79(16) . . ? C29 C28 C37 117.83(16) . . ? C30 C29 C28 120.86(16) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C29 C30 C35 120.78(17) . . ? C29 C30 C31 126.91(17) . . ? C35 C30 C31 112.24(16) . . ? C30 C31 C51 107.63(18) . . ? C30 C31 C32 106.33(18) . . ? C51 C31 C32 106.16(17) . . ? C30 C31 H31 112.1 . . ? C51 C31 H31 112.1 . . ? C32 C31 H31 112.1 . . ? C33 C32 C31 111.36(19) . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C31 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C32 C33 C34 110.47(18) . . ? C32 C33 H33A 109.6 . . ? C34 C33 H33A 109.6 . . ? C32 C33 H33B 109.6 . . ? C34 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? C35 C34 C52 107.70(17) . . ? C35 C34 C33 106.64(17) . . ? C52 C34 C33 106.30(18) . . ? C35 C34 H34 111.9 . . ? C52 C34 H34 111.9 . . ? C33 C34 H34 111.9 . . ? C36 C35 C30 120.14(17) . . ? C36 C35 C34 127.59(17) . . ? C30 C35 C34 112.23(17) . . ? C35 C36 C37 120.95(17) . . ? C35 C36 H36 119.5 . . ? C37 C36 H36 119.5 . . ? C38 C37 C36 121.49(16) . . ? C38 C37 C28 119.05(16) . . ? C36 C37 C28 119.39(16) . . ? C37 C38 C39 122.08(16) . . ? C37 C38 H38 119.0 . . ? C39 C38 H38 119.0 . . ? C38 C39 C40 121.45(16) . . ? C38 C39 C48 119.45(16) . . ? C40 C39 C48 119.09(16) . . ? C41 C40 C39 120.83(17) . . ? C41 C40 H40 119.6 . . ? C39 C40 H40 119.6 . . ? C40 C41 C46 120.35(17) . . ? C40 C41 C42 127.13(18) . . ? C46 C41 C42 112.50(17) . . ? C41 C42 C50 106.43(17) . . ? C41 C42 C43 107.65(17) . . ? C50 C42 C43 106.38(19) . . ? C41 C42 H42 112.0 . . ? C50 C42 H42 112.0 . . ? C43 C42 H42 112.0 . . ? C44 C43 C42 112.08(19) . . ? C44 C43 H43 124.0 . . ? C42 C43 H43 124.0 . . ? C43 C44 C45 112.92(19) . . ? C43 C44 H44 123.5 . . ? C45 C44 H44 123.5 . . ? C46 C45 C49 106.09(17) . . ? C46 C45 C44 107.43(17) . . ? C49 C45 C44 106.19(17) . . ? C46 C45 H45 112.2 . . ? C49 C45 H45 112.2 . . ? C44 C45 H45 112.2 . . ? C47 C46 C41 120.69(17) . . ? C47 C46 C45 127.11(17) . . ? C41 C46 C45 112.16(16) . . ? C46 C47 C48 120.82(16) . . ? C46 C47 H47 119.6 . . ? C48 C47 H47 119.6 . . ? C27 C48 C47 122.62(15) . . ? C27 C48 C39 119.18(16) . . ? C47 C48 C39 118.20(15) . . ? C50 C49 C45 111.50(18) . . ? C50 C49 H49A 109.3 . . ? C45 C49 H49A 109.3 . . ? C50 C49 H49B 109.3 . . ? C45 C49 H49B 109.3 . . ? H49A C49 H49B 108.0 . . ? C49 C50 C42 111.54(18) . . ? C49 C50 H50A 109.3 . . ? C42 C50 H50A 109.3 . . ? C49 C50 H50B 109.3 . . ? C42 C50 H50B 109.3 . . ? H50A C50 H50B 108.0 . . ? C52 C51 C31 113.29(18) . . ? C52 C51 H51 123.4 . . ? C31 C51 H51 123.4 . . ? C51 C52 C34 112.53(19) . . ? C51 C52 H52 123.7 . . ? C34 C52 H52 123.7 . . ? C58A O2 C58 121.2(11) . . ? O2 C58 C57 111.3(12) . . ? O2 C58 H66 109.4 . . ? C57 C58 H66 109.4 . . ? O2 C58 H67 109.4 . . ? C57 C58 H67 109.4 . . ? H66 C58 H67 108.0 . . ? O2 C58A C59 113.1(8) . . ? O2 C58A H71 109.0 . . ? C59 C58A H71 109.0 . . ? O2 C58A H72 109.0 . . ? C59 C58A H72 109.0 . . ? H71 C58A H72 107.8 . . ? 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 C55 O1 C54 C56 -178.0(8) . . . . ? C54 O1 C55 C53 177.0(9) . . . . ? C22 C1 C2 C3 178.42(16) . . . . ? C22 C1 C2 C11 -1.1(3) . . . . ? C1 C2 C3 C4 -178.66(16) . . . . ? C11 C2 C3 C4 0.8(3) . . . . ? C2 C3 C4 C9 0.1(3) . . . . ? C2 C3 C4 C5 178.98(17) . . . . ? C3 C4 C5 C6 126.3(2) . . . . ? C9 C4 C5 C6 -54.8(2) . . . . ? C3 C4 C5 C25 -119.9(2) . . . . ? C9 C4 C5 C25 59.05(19) . . . . ? C4 C5 C6 C7 55.7(2) . . . . ? C25 C5 C6 C7 -58.0(2) . . . . ? C5 C6 C7 C8 -0.4(2) . . . . ? C6 C7 C8 C9 -55.8(2) . . . . ? C6 C7 C8 C26 57.8(2) . . . . ? C3 C4 C9 C10 -1.3(3) . . . . ? C5 C4 C9 C10 179.73(16) . . . . ? C3 C4 C9 C8 177.69(16) . . . . ? C5 C4 C9 C8 -1.3(2) . . . . ? C7 C8 C9 C10 -124.64(19) . . . . ? C26 C8 C9 C10 122.35(19) . . . . ? C7 C8 C9 C4 56.5(2) . . . . ? C26 C8 C9 C4 -56.5(2) . . . . ? C4 C9 C10 C11 1.4(3) . . . . ? C8 C9 C10 C11 -177.36(16) . . . . ? C9 C10 C11 C12 178.34(16) . . . . ? C9 C10 C11 C2 -0.5(2) . . . . ? C1 C2 C11 C12 0.0(2) . . . . ? C3 C2 C11 C12 -179.48(15) . . . . ? C1 C2 C11 C10 178.84(15) . . . . ? C3 C2 C11 C10 -0.6(2) . . . . ? C10 C11 C12 C13 -177.42(15) . . . . ? C2 C11 C12 C13 1.4(2) . . . . ? C10 C11 C12 C27 1.0(2) . . . . ? C2 C11 C12 C27 179.82(14) . . . . ? C11 C12 C13 C14 176.11(15) . . . . ? C27 C12 C13 C14 -2.4(2) . . . . ? C11 C12 C13 C22 -1.7(2) . . . . ? C27 C12 C13 C22 179.84(14) . . . . ? C12 C13 C14 C15 -176.57(16) . . . . ? C22 C13 C14 C15 1.3(3) . . . . ? C13 C14 C15 C20 -1.1(3) . . . . ? C13 C14 C15 C16 177.09(17) . . . . ? C14 C15 C16 C24 125.8(2) . . . . ? C20 C15 C16 C24 -55.9(2) . . . . ? C14 C15 C16 C17 -120.8(2) . . . . ? C20 C15 C16 C17 57.5(2) . . . . ? C15 C16 C17 C18 -56.8(2) . . . . ? C24 C16 C17 C18 57.5(2) . . . . ? C16 C17 C18 C19 -0.1(3) . . . . ? C17 C18 C19 C20 56.9(3) . . . . ? C17 C18 C19 C23 -57.2(2) . . . . ? C14 C15 C20 C21 -0.4(3) . . . . ? C16 C15 C20 C21 -178.85(18) . . . . ? C14 C15 C20 C19 177.93(18) . . . . ? C16 C15 C20 C19 -0.5(2) . . . . ? C23 C19 C20 C21 -125.5(2) . . . . ? C18 C19 C20 C21 121.3(2) . . . . ? C23 C19 C20 C15 56.3(2) . . . . ? C18 C19 C20 C15 -56.9(2) . . . . ? C15 C20 C21 C22 1.8(3) . . . . ? C19 C20 C21 C22 -176.29(19) . . . . ? C2 C1 C22 C21 -176.51(16) . . . . ? C2 C1 C22 C13 0.7(3) . . . . ? C20 C21 C22 C1 175.66(17) . . . . ? C20 C21 C22 C13 -1.6(3) . . . . ? C12 C13 C22 C1 0.7(2) . . . . ? C14 C13 C22 C1 -177.22(16) . . . . ? C12 C13 C22 C21 177.96(16) . . . . ? C14 C13 C22 C21 0.1(2) . . . . ? C20 C19 C23 C24 -55.8(2) . . . . ? C18 C19 C23 C24 57.8(2) . . . . ? C19 C23 C24 C16 -0.4(3) . . . . ? C15 C16 C24 C23 56.1(2) . . . . ? C17 C16 C24 C23 -57.3(2) . . . . ? C4 C5 C25 C26 -57.2(2) . . . . ? C6 C5 C25 C26 57.3(2) . . . . ? C5 C25 C26 C8 0.0(2) . . . . ? C9 C8 C26 C25 57.0(2) . . . . ? C7 C8 C26 C25 -56.9(2) . . . . ? C13 C12 C27 C28 85.9(2) . . . . ? C11 C12 C27 C28 -92.6(2) . . . . ? C13 C12 C27 C48 -91.70(19) . . . . ? C11 C12 C27 C48 89.8(2) . . . . ? C48 C27 C28 C29 174.08(15) . . . . ? C12 C27 C28 C29 -3.5(3) . . . . ? C48 C27 C28 C37 -3.2(2) . . . . ? C12 C27 C28 C37 179.22(14) . . . . ? C27 C28 C29 C30 -175.79(17) . . . . ? C37 C28 C29 C30 1.6(3) . . . . ? C28 C29 C30 C35 -1.1(3) . . . . ? C28 C29 C30 C31 175.82(19) . . . . ? C29 C30 C31 C51 128.0(2) . . . . ? C35 C30 C31 C51 -54.9(2) . . . . ? C29 C30 C31 C32 -118.6(2) . . . . ? C35 C30 C31 C32 58.6(2) . . . . ? C30 C31 C32 C33 -57.8(2) . . . . ? C51 C31 C32 C33 56.6(2) . . . . ? C31 C32 C33 C34 0.2(3) . . . . ? C32 C33 C34 C35 57.4(2) . . . . ? C32 C33 C34 C52 -57.3(2) . . . . ? C29 C30 C35 C36 -0.8(3) . . . . ? C31 C30 C35 C36 -178.17(19) . . . . ? C29 C30 C35 C34 177.09(18) . . . . ? C31 C30 C35 C34 -0.3(3) . . . . ? C52 C34 C35 C36 -126.9(2) . . . . ? C33 C34 C35 C36 119.3(2) . . . . ? C52 C34 C35 C30 55.4(2) . . . . ? C33 C34 C35 C30 -58.4(2) . . . . ? C30 C35 C36 C37 2.2(3) . . . . ? C34 C35 C36 C37 -175.32(19) . . . . ? C35 C36 C37 C38 175.40(17) . . . . ? C35 C36 C37 C28 -1.7(3) . . . . ? C27 C28 C37 C38 0.1(2) . . . . ? C29 C28 C37 C38 -177.37(16) . . . . ? C27 C28 C37 C36 177.25(16) . . . . ? C29 C28 C37 C36 -0.2(2) . . . . ? C36 C37 C38 C39 -174.27(16) . . . . ? C28 C37 C38 C39 2.9(3) . . . . ? C37 C38 C39 C40 175.78(16) . . . . ? C37 C38 C39 C48 -2.5(3) . . . . ? C38 C39 C40 C41 -177.81(17) . . . . ? C48 C39 C40 C41 0.5(3) . . . . ? C39 C40 C41 C46 0.0(3) . . . . ? C39 C40 C41 C42 -178.39(18) . . . . ? C40 C41 C42 C50 121.0(2) . . . . ? C46 C41 C42 C50 -57.5(2) . . . . ? C40 C41 C42 C43 -125.3(2) . . . . ? C46 C41 C42 C43 56.2(2) . . . . ? C41 C42 C43 C44 -55.6(2) . . . . ? C50 C42 C43 C44 58.2(2) . . . . ? C42 C43 C44 C45 -0.5(3) . . . . ? C43 C44 C45 C46 56.0(2) . . . . ? C43 C44 C45 C49 -57.2(2) . . . . ? C40 C41 C46 C47 -1.1(3) . . . . ? C42 C41 C46 C47 177.56(18) . . . . ? C40 C41 C46 C45 -179.16(17) . . . . ? C42 C41 C46 C45 -0.6(2) . . . . ? C49 C45 C46 C47 -119.8(2) . . . . ? C44 C45 C46 C47 126.9(2) . . . . ? C49 C45 C46 C41 58.1(2) . . . . ? C44 C45 C46 C41 -55.1(2) . . . . ? C41 C46 C47 C48 1.5(3) . . . . ? C45 C46 C47 C48 179.34(17) . . . . ? C28 C27 C48 C47 -175.43(15) . . . . ? C12 C27 C48 C47 2.1(2) . . . . ? C28 C27 C48 C39 3.5(2) . . . . ? C12 C27 C48 C39 -178.92(15) . . . . ? C46 C47 C48 C27 177.98(16) . . . . ? C46 C47 C48 C39 -1.0(3) . . . . ? C38 C39 C48 C27 -0.7(2) . . . . ? C40 C39 C48 C27 -179.05(15) . . . . ? C38 C39 C48 C47 178.32(16) . . . . ? C40 C39 C48 C47 -0.1(2) . . . . ? C46 C45 C49 C50 -57.4(2) . . . . ? C44 C45 C49 C50 56.7(2) . . . . ? C45 C49 C50 C42 0.0(3) . . . . ? C41 C42 C50 C49 57.2(2) . . . . ? C43 C42 C50 C49 -57.4(2) . . . . ? C30 C31 C51 C52 55.7(2) . . . . ? C32 C31 C51 C52 -57.8(2) . . . . ? C31 C51 C52 C34 -0.3(3) . . . . ? C35 C34 C52 C51 -55.3(2) . . . . ? C33 C34 C52 C51 58.6(2) . . . . ? C58A O2 C58 C57 -178.1(4) . . . . ? C58 O2 C58A C59 -175.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.513 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 923855' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_20911kab #TrackingRef '8dBPBr.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C52 H40 Br2), 0.37(C2 Cl6), C Cl3, 1.13(C2 O2) ' _chemical_formula_sum 'C53.33 H40 Br2 Cl1.74 O0.75' _chemical_formula_weight 914.38 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _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 41.930(4) _cell_length_b 15.3835(14) _cell_length_c 18.8623(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.9120(10) _cell_angle_gamma 90.00 _cell_volume 11859.0(19) _cell_formula_units_Z 12 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 5905 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 24.77 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5587 _exptl_absorpt_coefficient_mu 2.210 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6737 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30227 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -51 _diffrn_reflns_limit_h_max 51 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 26.00 _reflns_number_total 11559 _reflns_number_gt 7013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1693P)^2^+133.7087P] 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 11559 _refine_ls_number_parameters 820 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1482 _refine_ls_R_factor_gt 0.0994 _refine_ls_wR_factor_ref 0.3153 _refine_ls_wR_factor_gt 0.2790 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2204(2) 0.4901(5) 0.1676(5) 0.040(2) Uani 1 1 d . . . H1 H 0.2137 0.5218 0.2062 0.047 Uiso 1 1 calc R . . H2 H 0.2140 0.4299 0.1704 0.047 Uiso 1 1 calc R . . C2 C 0.2569(2) 0.4949(5) 0.1789(5) 0.039(2) Uani 1 1 d . . . H3 H 0.2662 0.4372 0.1873 0.046 Uiso 1 1 calc R . . H4 H 0.2658 0.5305 0.2211 0.046 Uiso 1 1 calc R . . C3 C 0.2656(2) 0.5358(5) 0.1091(5) 0.041(2) Uani 1 1 d . . . H5 H 0.2893 0.5394 0.1137 0.049 Uiso 1 1 calc R . . C4 C 0.2493(3) 0.4821(5) 0.0443(4) 0.042(2) Uani 1 1 d . . . H6 H 0.2607 0.4541 0.0139 0.050 Uiso 1 1 calc R . . C5 C 0.2160(2) 0.4788(5) 0.0347(4) 0.039(2) Uani 1 1 d . . . H7 H 0.2025 0.4501 -0.0040 0.046 Uiso 1 1 calc R . . C6 C 0.2030(2) 0.5276(5) 0.0945(5) 0.0356(18) Uani 1 1 d . . . H8 H 0.1791 0.5241 0.0869 0.043 Uiso 1 1 calc R . . C7 C 0.21501(19) 0.6205(5) 0.0941(4) 0.0294(16) Uani 1 1 d . . . C8 C 0.19672(18) 0.6940(4) 0.0896(4) 0.0248(15) Uani 1 1 d . . . H9 H 0.1741 0.6895 0.0824 0.030 Uiso 1 1 calc R . . C9 C 0.21171(16) 0.7786(5) 0.0956(4) 0.0227(15) Uani 1 1 d . . . C10 C 0.19399(16) 0.8553(4) 0.0965(3) 0.0199(14) Uani 1 1 d . . . C11 C 0.20967(16) 0.9355(5) 0.1088(3) 0.0214(14) Uani 1 1 d . . . C12 C 0.19182(18) 1.0135(5) 0.1131(4) 0.0261(16) Uani 1 1 d . . . H10 H 0.1692 1.0112 0.1064 0.031 Uiso 1 1 calc R . . C13 C 0.2076(2) 1.0924(5) 0.1270(4) 0.0329(17) Uani 1 1 d . . . C14 C 0.1924(2) 1.1793(5) 0.1320(5) 0.043(2) Uani 1 1 d . . . H11 H 0.1685 1.1761 0.1235 0.051 Uiso 1 1 calc R . . C15 C 0.2084(2) 1.2162(6) 0.2091(4) 0.040(2) Uani 1 1 d . . . H12 H 0.1996 1.2736 0.2146 0.048 Uiso 1 1 calc R . . H13 H 0.2031 1.1787 0.2462 0.048 Uiso 1 1 calc R . . C16 C 0.2436(2) 1.2214(5) 0.2185(4) 0.039(2) Uani 1 1 d . . . H14 H 0.2539 1.1877 0.2609 0.046 Uiso 1 1 calc R . . H15 H 0.2504 1.2814 0.2274 0.046 Uiso 1 1 calc R . . C17 C 0.2553(2) 1.1883(5) 0.1533(5) 0.043(2) Uani 1 1 d . . . H16 H 0.2792 1.1915 0.1603 0.051 Uiso 1 1 calc R . . C18 C 0.2379(3) 1.2417(6) 0.0892(5) 0.060(3) Uani 1 1 d . . . H17 H 0.2488 1.2737 0.0603 0.072 Uiso 1 1 calc R . . C19 C 0.2038(3) 1.2389(7) 0.0772(5) 0.066(3) Uani 1 1 d . . . H18 H 0.1898 1.2694 0.0405 0.080 Uiso 1 1 calc R . . C20 C 0.2425(2) 1.0961(5) 0.1373(4) 0.0340(18) Uani 1 1 d . . . C21 C 0.26027(19) 1.0238(5) 0.1342(4) 0.0306(17) Uani 1 1 d . . . H19 H 0.2829 1.0280 0.1417 0.037 Uiso 1 1 calc R . . C22 C 0.24479(17) 0.9400(5) 0.1195(4) 0.0243(15) Uani 1 1 d . . . C23 C 0.26152(17) 0.8640(5) 0.1138(4) 0.0280(16) Uani 1 1 d . . . C24 C 0.24677(17) 0.7826(5) 0.1027(4) 0.0239(15) Uani 1 1 d . . . C25 C 0.26456(18) 0.7033(5) 0.1030(4) 0.0274(16) Uani 1 1 d . . . H20 H 0.2869 0.7054 0.1050 0.033 Uiso 1 1 calc R . . C26 C 0.24959(19) 0.6259(5) 0.1005(4) 0.0323(18) Uani 1 1 d . . . Br1 Br 0.30746(2) 0.86934(7) 0.12117(6) 0.0563(3) Uani 1 1 d . . . C27 C 0.1208(3) 0.7417(6) 0.3757(5) 0.051(2) Uani 1 1 d . . . H21 H 0.1156 0.7332 0.4228 0.061 Uiso 1 1 calc R . . H22 H 0.1109 0.6946 0.3442 0.061 Uiso 1 1 calc R . . C28 C 0.1557(2) 0.7384(6) 0.3841(4) 0.043(2) Uani 1 1 d . . . H23 H 0.1612 0.6905 0.3556 0.052 Uiso 1 1 calc R . . H24 H 0.1659 0.7276 0.4347 0.052 Uiso 1 1 calc R . . C29 C 0.1692(2) 0.8228(6) 0.3598(4) 0.0388(19) Uani 1 1 d . . . H25 H 0.1930 0.8208 0.3658 0.047 Uiso 1 1 calc R . . C30 C 0.1584(2) 0.8975(6) 0.4031(5) 0.044(2) Uani 1 1 d . . . H26 H 0.1728 0.9367 0.4311 0.053 Uiso 1 1 calc R . . C31 C 0.1243(2) 0.9001(6) 0.3957(5) 0.048(2) Uani 1 1 d . . . H27 H 0.1135 0.9405 0.4187 0.058 Uiso 1 1 calc R . . C32 C 0.1065(2) 0.8269(6) 0.3440(5) 0.039(2) Uani 1 1 d . . . H28 H 0.0827 0.8289 0.3386 0.047 Uiso 1 1 calc R . . C33 C 0.1162(2) 0.8383(5) 0.2722(5) 0.0317(18) Uani 1 1 d . . . C34 C 0.09635(19) 0.8465(5) 0.2048(5) 0.0334(18) Uani 1 1 d . . . H29 H 0.0738 0.8495 0.2003 0.040 Uiso 1 1 calc R . . C35 C 0.10888(17) 0.8505(5) 0.1418(4) 0.0264(16) Uani 1 1 d . . . C36 C 0.08946(16) 0.8538(5) 0.0708(5) 0.0280(16) Uani 1 1 d . . . C37 C 0.10236(17) 0.8549(4) 0.0078(4) 0.0255(15) Uani 1 1 d . . . C38 C 0.08199(18) 0.8547(5) -0.0638(5) 0.0341(18) Uani 1 1 d . . . H30 H 0.0594 0.8542 -0.0701 0.041 Uiso 1 1 calc R . . C39 C 0.0957(2) 0.8552(5) -0.1231(4) 0.0335(18) Uani 1 1 d . . . C40 C 0.0781(2) 0.8536(6) -0.2031(5) 0.041(2) Uani 1 1 d . . . H31 H 0.0543 0.8521 -0.2095 0.049 Uiso 1 1 calc R . . C41 C 0.0894(2) 0.9320(6) -0.2380(5) 0.043(2) Uani 1 1 d . . . H32 H 0.0784 0.9333 -0.2890 0.052 Uiso 1 1 calc R . . H33 H 0.0832 0.9840 -0.2153 0.052 Uiso 1 1 calc R . . C42 C 0.1239(2) 0.9327(6) -0.2321(5) 0.045(2) Uani 1 1 d . . . H34 H 0.1329 0.9869 -0.2098 0.054 Uiso 1 1 calc R . . H35 H 0.1284 0.9298 -0.2803 0.054 Uiso 1 1 calc R . . C43 C 0.14090(19) 0.8556(6) -0.1861(4) 0.0356(18) Uani 1 1 d . . . H36 H 0.1647 0.8571 -0.1798 0.043 Uiso 1 1 calc R . . C44 C 0.1256(2) 0.7733(6) -0.2270(5) 0.042(2) Uani 1 1 d . . . H37 H 0.1374 0.7295 -0.2435 0.051 Uiso 1 1 calc R . . C45 C 0.0912(2) 0.7736(6) -0.2358(5) 0.051(2) Uani 1 1 d . . . H38 H 0.0778 0.7294 -0.2594 0.061 Uiso 1 1 calc R . . C46 C 0.13064(18) 0.8565(5) -0.1149(4) 0.0292(16) Uani 1 1 d . . . C47 C 0.15053(17) 0.8565(5) -0.0463(4) 0.0261(15) Uani 1 1 d . . . H39 H 0.1731 0.8579 -0.0410 0.031 Uiso 1 1 calc R . . C48 C 0.13719(17) 0.8545(4) 0.0174(4) 0.0239(15) Uani 1 1 d . . . C49 C 0.15768(17) 0.8518(4) 0.0875(4) 0.0224(14) Uani 1 1 d . . . C50 C 0.14445(17) 0.8490(4) 0.1488(4) 0.0234(15) Uani 1 1 d . . . C51 C 0.16463(17) 0.8408(5) 0.2207(4) 0.0259(16) Uani 1 1 d . . . H40 H 0.1872 0.8389 0.2267 0.031 Uiso 1 1 calc R . . C52 C 0.15153(19) 0.8356(5) 0.2803(4) 0.0302(17) Uani 1 1 d . . . Br2 Br 0.04379(2) 0.85118(8) 0.06151(7) 0.0617(4) Uani 1 1 d . . . C53 C 0.0000 0.4465(7) 0.2500 0.042(3) Uani 1 2 d S . . C54 C 0.0258(2) 0.4894(5) 0.2303(5) 0.041(2) Uani 1 1 d . . . C55 C 0.0517(2) 0.4457(6) 0.2072(6) 0.048(2) Uani 1 1 d . . . H41 H 0.0512 0.3854 0.2032 0.058 Uiso 1 1 calc R . . C56 C 0.0766(2) 0.4892(6) 0.1912(5) 0.045(2) Uani 1 1 d . . . C57 C 0.1060(2) 0.4506(6) 0.1673(6) 0.053(2) Uani 1 1 d . . . H42 H 0.1049 0.3871 0.1634 0.063 Uiso 1 1 calc R . . C58 C 0.1069(3) 0.4925(8) 0.0976(6) 0.066(3) Uani 1 1 d . . . H43 H 0.1257 0.4707 0.0808 0.079 Uiso 1 1 calc R . . H44 H 0.0874 0.4765 0.0617 0.079 Uiso 1 1 calc R . . C59 C 0.1090(3) 0.5860(7) 0.1026(6) 0.057(3) Uani 1 1 d . . . H45 H 0.0906 0.6113 0.0683 0.068 Uiso 1 1 calc R . . H46 H 0.1289 0.6053 0.0895 0.068 Uiso 1 1 calc R . . C60 C 0.1087(2) 0.6177(5) 0.1771(6) 0.048(2) Uani 1 1 d . . . H47 H 0.1101 0.6811 0.1812 0.057 Uiso 1 1 calc R . . C61 C 0.1384(2) 0.5710(7) 0.2270(6) 0.060(3) Uani 1 1 d . . . H48 H 0.1557 0.6003 0.2572 0.072 Uiso 1 1 calc R . . C62 C 0.1364(3) 0.4813(8) 0.2216(6) 0.061(3) Uani 1 1 d . . . H49 H 0.1520 0.4438 0.2483 0.074 Uiso 1 1 calc R . . C63 C 0.0786(2) 0.5813(5) 0.1968(5) 0.0391(19) Uani 1 1 d . . . C64 C 0.0534(2) 0.6266(5) 0.2150(5) 0.0385(19) Uani 1 1 d . . . H50 H 0.0542 0.6870 0.2161 0.046 Uiso 1 1 calc R . . C65 C 0.02625(19) 0.5840(5) 0.2323(4) 0.0333(18) Uani 1 1 d . . . C66 C 0.0000 0.6291(7) 0.2500 0.033(2) Uani 1 2 d S . . C67 C 0.0000 0.7259(7) 0.2500 0.028(2) Uani 1 2 d S . . C68 C 0.01284(17) 0.7717(5) 0.3149(4) 0.0269(16) Uani 1 1 d . . . C69 C 0.0257(2) 0.7268(5) 0.3814(4) 0.0366(19) Uani 1 1 d . . . H51 H 0.0254 0.6663 0.3821 0.044 Uiso 1 1 calc R . . C70 C 0.0387(2) 0.7713(6) 0.4446(4) 0.040(2) Uani 1 1 d . . . C71 C 0.0519(2) 0.7328(8) 0.5192(5) 0.058(3) Uani 1 1 d . . . H52 H 0.0513 0.6691 0.5190 0.069 Uiso 1 1 calc R . . C72 C 0.0856(3) 0.7678(9) 0.5472(5) 0.061(3) Uani 1 1 d . . . H53 H 0.0940 0.7460 0.5960 0.073 Uiso 1 1 calc R . . H54 H 0.0997 0.7466 0.5168 0.073 Uiso 1 1 calc R . . C73 C 0.0867(3) 0.8598(10) 0.5486(5) 0.071(4) Uani 1 1 d . . . H55 H 0.1015 0.8796 0.5192 0.085 Uiso 1 1 calc R . . H56 H 0.0954 0.8790 0.5981 0.085 Uiso 1 1 calc R . . C74 C 0.0526(2) 0.9022(8) 0.5199(5) 0.056(3) Uani 1 1 d . . . H57 H 0.0532 0.9659 0.5202 0.067 Uiso 1 1 calc R . . C75 C 0.0320(3) 0.8649(8) 0.5685(5) 0.059(3) Uani 1 1 d . . . H58 H 0.0212 0.8995 0.5960 0.071 Uiso 1 1 calc R . . C76 C 0.0304(3) 0.7733(11) 0.5691(5) 0.078(4) Uani 1 1 d . . . H59 H 0.0183 0.7413 0.5956 0.094 Uiso 1 1 calc R . . C77 C 0.03913(19) 0.8640(6) 0.4446(4) 0.0367(19) Uani 1 1 d . . . C78 C 0.02682(17) 0.9095(5) 0.3820(4) 0.0294(17) Uani 1 1 d . . . H60 H 0.0274 0.9700 0.3829 0.035 Uiso 1 1 calc R . . C79 C 0.01292(16) 0.8653(5) 0.3146(4) 0.0239(15) Uani 1 1 d . . . C80 C 0.0000 0.9077(6) 0.2500 0.021(2) Uani 1 2 d S . . Br3 Br 0.0000 0.32154(10) 0.2500 0.0855(7) Uani 1 2 d S . . Br4 Br 0.0000 1.03090(8) 0.2500 0.0507(4) Uani 1 2 d S . . Cl1 Cl 0.1185(2) 0.3713(5) 0.4269(4) 0.0769(19) Uani 0.50 1 d P A -2 Cl2 Cl 0.0809(4) 0.5333(6) 0.3984(5) 0.124(4) Uani 0.50 1 d P A -2 Cl3 Cl 0.0526(2) 0.3730(7) 0.4238(6) 0.131(3) Uani 0.50 1 d P A -2 C81 C 0.0802(8) 0.427(2) 0.3902(17) 0.090(8) Uiso 0.50 1 d P A -2 Cl4 Cl 0.0587(4) 0.4962(10) 0.4185(6) 0.125(6) Uani 0.373(11) 1 d PD B -1 Cl5 Cl -0.0046(4) 0.5292(16) 0.4635(12) 0.193(10) Uani 0.373(11) 1 d PD B -1 Cl6 Cl 0.0309(6) 0.3626(13) 0.5059(14) 0.33(3) Uani 0.373(11) 1 d PD B -1 C82 C 0.0239(12) 0.454(3) 0.446(4) 0.29(6) Uiso 0.373(11) 1 d PD B -1 O1 O 0.1357(3) 0.5332(9) 0.4345(7) 0.053(3) Uiso 0.50 1 d PD B -1 O2 O 0.0936(13) 0.371(3) 0.402(2) 0.195(17) Uiso 0.50 1 d PD B -1 C84 C 0.1069(10) 0.488(3) 0.393(2) 0.134(14) Uiso 0.50 1 d PD B -1 C85 C 0.1250(17) 0.415(7) 0.421(5) 0.27(5) Uiso 0.50 1 d PD B -1 O3 O -0.0173(12) 0.576(3) 0.459(3) 0.036(12) Uiso 0.127(11) 1 d PD B -3 C83 C -0.0015(15) 0.495(3) 0.481(3) 0.016(13) Uiso 0.127(11) 1 d PD B -3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.049(5) 0.031(4) 0.041(5) -0.004(4) 0.014(4) 0.004(4) C2 0.052(5) 0.028(4) 0.035(4) 0.004(3) 0.007(4) 0.010(4) C3 0.039(5) 0.028(4) 0.057(6) 0.003(4) 0.012(4) 0.014(4) C4 0.076(7) 0.031(4) 0.023(4) 0.001(3) 0.020(4) 0.016(4) C5 0.055(6) 0.030(4) 0.026(4) -0.005(3) -0.002(4) 0.010(4) C6 0.039(5) 0.028(4) 0.041(5) 0.000(4) 0.012(4) 0.006(3) C7 0.036(4) 0.027(4) 0.026(4) -0.001(3) 0.007(3) 0.006(3) C8 0.024(4) 0.021(4) 0.029(4) 0.001(3) 0.004(3) 0.002(3) C9 0.022(3) 0.031(4) 0.017(3) 0.001(3) 0.007(3) 0.001(3) C10 0.019(3) 0.025(3) 0.015(3) -0.003(3) 0.003(3) 0.001(3) C11 0.022(3) 0.027(4) 0.014(3) -0.001(3) 0.003(3) -0.003(3) C12 0.021(4) 0.026(4) 0.029(4) 0.000(3) 0.001(3) -0.005(3) C13 0.039(4) 0.030(4) 0.027(4) -0.001(3) 0.003(3) -0.004(3) C14 0.050(5) 0.027(4) 0.047(5) -0.010(4) 0.000(4) -0.005(4) C15 0.058(6) 0.035(5) 0.025(4) -0.008(3) 0.006(4) -0.001(4) C16 0.058(6) 0.030(4) 0.027(4) -0.008(3) 0.009(4) -0.016(4) C17 0.057(6) 0.033(5) 0.043(5) -0.011(4) 0.019(4) -0.022(4) C18 0.103(9) 0.040(5) 0.040(5) -0.002(4) 0.022(6) -0.033(6) C19 0.108(10) 0.040(5) 0.037(5) 0.013(4) -0.015(6) -0.012(6) C20 0.044(5) 0.033(4) 0.025(4) -0.005(3) 0.009(3) -0.014(4) C21 0.025(4) 0.042(5) 0.024(4) -0.008(3) 0.005(3) -0.013(3) C22 0.028(4) 0.029(4) 0.017(3) -0.003(3) 0.005(3) -0.002(3) C23 0.015(3) 0.044(5) 0.025(4) 0.003(3) 0.005(3) -0.002(3) C24 0.024(4) 0.031(4) 0.015(3) 0.003(3) 0.002(3) 0.005(3) C25 0.021(4) 0.036(4) 0.026(4) -0.003(3) 0.009(3) 0.006(3) C26 0.032(4) 0.034(4) 0.030(4) 0.000(3) 0.007(3) 0.014(3) Br1 0.0326(5) 0.0712(7) 0.0647(7) 0.0021(5) 0.0098(4) -0.0031(4) C27 0.074(7) 0.046(5) 0.041(5) -0.005(4) 0.032(5) -0.015(5) C28 0.061(6) 0.044(5) 0.027(4) -0.003(4) 0.015(4) -0.003(4) C29 0.038(5) 0.052(5) 0.027(4) -0.005(4) 0.009(4) -0.001(4) C30 0.048(5) 0.053(6) 0.034(5) -0.014(4) 0.013(4) -0.017(4) C31 0.064(6) 0.053(6) 0.035(5) -0.011(4) 0.027(4) -0.002(5) C32 0.033(4) 0.046(5) 0.043(5) -0.009(4) 0.018(4) -0.011(4) C33 0.034(4) 0.025(4) 0.040(5) -0.007(3) 0.018(4) -0.003(3) C34 0.026(4) 0.028(4) 0.049(5) -0.009(4) 0.015(4) -0.005(3) C35 0.019(3) 0.019(3) 0.041(4) -0.008(3) 0.005(3) -0.002(3) C36 0.010(3) 0.023(4) 0.050(5) 0.002(3) 0.003(3) 0.001(3) C37 0.020(3) 0.016(3) 0.036(4) 0.003(3) -0.002(3) 0.002(3) C38 0.019(4) 0.027(4) 0.050(5) 0.002(4) -0.007(3) -0.003(3) C39 0.035(4) 0.026(4) 0.031(4) 0.002(3) -0.009(3) -0.003(3) C40 0.030(4) 0.040(5) 0.042(5) 0.006(4) -0.013(4) -0.005(4) C41 0.040(5) 0.047(5) 0.032(4) 0.008(4) -0.013(4) 0.004(4) C42 0.061(6) 0.039(5) 0.028(4) 0.000(4) -0.001(4) -0.007(4) C43 0.026(4) 0.052(5) 0.024(4) -0.002(4) -0.005(3) 0.001(4) C44 0.048(5) 0.037(5) 0.038(5) -0.012(4) 0.003(4) 0.000(4) C45 0.053(6) 0.049(6) 0.041(5) -0.008(4) -0.010(4) -0.010(5) C46 0.029(4) 0.026(4) 0.029(4) 0.002(3) -0.002(3) -0.003(3) C47 0.020(3) 0.025(4) 0.030(4) 0.001(3) -0.001(3) -0.001(3) C48 0.020(3) 0.018(3) 0.031(4) 0.000(3) 0.000(3) 0.003(3) C49 0.021(3) 0.017(3) 0.026(4) -0.006(3) 0.001(3) -0.002(3) C50 0.022(4) 0.015(3) 0.033(4) -0.002(3) 0.006(3) 0.000(3) C51 0.020(3) 0.024(4) 0.032(4) -0.004(3) 0.003(3) 0.001(3) C52 0.034(4) 0.027(4) 0.030(4) -0.002(3) 0.007(3) -0.002(3) Br2 0.0276(5) 0.0810(8) 0.0754(8) 0.0121(6) 0.0094(5) 0.0012(5) C53 0.048(7) 0.018(5) 0.063(8) 0.000 0.018(6) 0.000 C54 0.044(5) 0.017(4) 0.060(6) 0.000(4) 0.008(4) -0.002(3) C55 0.043(5) 0.031(5) 0.071(6) -0.006(4) 0.012(5) -0.001(4) C56 0.051(6) 0.036(5) 0.050(6) 0.001(4) 0.016(5) 0.005(4) C57 0.057(6) 0.029(5) 0.074(7) -0.003(5) 0.018(5) 0.004(4) C58 0.056(7) 0.088(9) 0.055(7) -0.023(6) 0.013(5) -0.004(6) C59 0.052(6) 0.057(6) 0.062(7) 0.013(5) 0.012(5) 0.000(5) C60 0.047(5) 0.023(4) 0.073(7) -0.006(4) 0.011(5) -0.002(4) C61 0.041(5) 0.063(7) 0.072(7) -0.031(6) 0.003(5) -0.006(5) C62 0.048(6) 0.075(8) 0.062(7) 0.003(6) 0.013(5) 0.014(5) C63 0.047(5) 0.025(4) 0.043(5) 0.000(4) 0.004(4) 0.000(4) C64 0.041(5) 0.023(4) 0.049(5) -0.004(4) 0.004(4) 0.000(3) C65 0.032(4) 0.027(4) 0.038(4) 0.001(3) 0.002(3) -0.004(3) C66 0.035(6) 0.033(6) 0.026(6) 0.000 -0.003(5) 0.000 C67 0.020(5) 0.031(6) 0.030(6) 0.000 -0.002(4) 0.000 C68 0.027(4) 0.028(4) 0.026(4) 0.001(3) 0.006(3) -0.002(3) C69 0.045(5) 0.028(4) 0.033(4) 0.004(3) -0.001(4) 0.000(4) C70 0.037(5) 0.055(6) 0.028(4) 0.007(4) 0.003(3) -0.001(4) C71 0.054(6) 0.078(7) 0.032(5) 0.012(5) -0.010(4) 0.007(5) C72 0.051(6) 0.100(10) 0.028(5) 0.007(5) 0.004(4) 0.002(6) C73 0.042(6) 0.144(13) 0.022(5) -0.006(6) -0.002(4) -0.011(7) C74 0.056(6) 0.078(7) 0.030(5) -0.025(5) -0.001(4) -0.004(5) C75 0.059(7) 0.087(9) 0.025(5) -0.016(5) -0.005(4) -0.005(6) C76 0.050(6) 0.160(15) 0.025(5) 0.023(7) 0.010(4) -0.015(8) C77 0.027(4) 0.052(5) 0.028(4) -0.014(4) -0.001(3) -0.004(4) C78 0.024(4) 0.031(4) 0.035(4) -0.014(3) 0.010(3) -0.008(3) C79 0.016(3) 0.028(4) 0.030(4) -0.004(3) 0.010(3) -0.003(3) C80 0.020(5) 0.014(4) 0.030(5) 0.000 0.010(4) 0.000 Br3 0.0884(13) 0.0294(7) 0.157(2) 0.000 0.0662(13) 0.000 Br4 0.0538(8) 0.0287(6) 0.0711(9) 0.000 0.0172(7) 0.000 Cl1 0.112(6) 0.065(4) 0.065(4) 0.000(3) 0.046(4) 0.023(4) Cl2 0.219(13) 0.068(5) 0.064(5) 0.018(4) -0.015(6) 0.004(6) Cl3 0.091(6) 0.132(8) 0.155(9) 0.007(7) -0.004(6) -0.019(5) Cl4 0.188(16) 0.118(11) 0.055(6) 0.025(6) -0.003(7) 0.073(10) Cl5 0.125(14) 0.24(3) 0.20(2) 0.074(18) 0.006(13) -0.013(16) Cl6 0.38(4) 0.21(3) 0.29(3) 0.14(2) -0.17(3) -0.22(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.496(12) . ? C1 C6 1.522(12) . ? C1 H1 0.9700 . ? C1 H2 0.9700 . ? C2 C3 1.575(12) . ? C2 H3 0.9700 . ? C2 H4 0.9700 . ? C3 C4 1.506(13) . ? C3 C26 1.533(10) . ? C3 H5 0.9800 . ? C4 C5 1.367(13) . ? C4 H6 0.9300 . ? C5 C6 1.553(11) . ? C5 H7 0.9300 . ? C6 C7 1.516(11) . ? C6 H8 0.9800 . ? C7 C8 1.358(10) . ? C7 C26 1.431(11) . ? C8 C9 1.439(10) . ? C8 H9 0.9300 . ? C9 C10 1.397(10) . ? C9 C24 1.447(10) . ? C10 C11 1.393(10) . ? C10 C49 1.495(9) . ? C11 C12 1.426(10) . ? C11 C22 1.443(10) . ? C12 C13 1.379(10) . ? C12 H10 0.9300 . ? C13 C20 1.433(12) . ? C13 C14 1.493(12) . ? C14 C19 1.537(14) . ? C14 C15 1.565(11) . ? C14 H11 0.9800 . ? C15 C16 1.451(12) . ? C15 H12 0.9700 . ? C15 H13 0.9700 . ? C16 C17 1.512(12) . ? C16 H14 0.9700 . ? C16 H15 0.9700 . ? C17 C18 1.508(15) . ? C17 C20 1.523(11) . ? C17 H16 0.9800 . ? C18 C19 1.394(17) . ? C18 H17 0.9300 . ? C19 H18 0.9300 . ? C20 C21 1.347(12) . ? C21 C22 1.442(10) . ? C21 H19 0.9300 . ? C22 C23 1.381(11) . ? C23 C24 1.391(11) . ? C23 Br1 1.901(7) . ? C24 C25 1.429(10) . ? C25 C26 1.343(11) . ? C25 H20 0.9300 . ? C27 C28 1.436(13) . ? C27 C32 1.510(14) . ? C27 H21 0.9700 . ? C27 H22 0.9700 . ? C28 C29 1.527(12) . ? C28 H23 0.9700 . ? C28 H24 0.9700 . ? C29 C52 1.529(11) . ? C29 C30 1.536(12) . ? C29 H25 0.9800 . ? C30 C31 1.407(13) . ? C30 H26 0.9300 . ? C31 C32 1.564(13) . ? C31 H27 0.9300 . ? C32 C33 1.509(12) . ? C32 H28 0.9800 . ? C33 C34 1.360(12) . ? C33 C52 1.457(11) . ? C34 C35 1.403(11) . ? C34 H29 0.9300 . ? C35 C36 1.405(11) . ? C35 C50 1.468(10) . ? C36 C37 1.410(11) . ? C36 Br2 1.884(7) . ? C37 C38 1.428(11) . ? C37 C48 1.431(10) . ? C38 C39 1.369(12) . ? C38 H30 0.9300 . ? C39 C46 1.437(11) . ? C39 C40 1.524(11) . ? C40 C41 1.502(12) . ? C40 C45 1.533(14) . ? C40 H31 0.9800 . ? C41 C42 1.426(13) . ? C41 H32 0.9700 . ? C41 H33 0.9700 . ? C42 C43 1.546(12) . ? C42 H34 0.9700 . ? C42 H35 0.9700 . ? C43 C46 1.500(11) . ? C43 C44 1.546(12) . ? C43 H36 0.9800 . ? C44 C45 1.412(13) . ? C44 H37 0.9300 . ? C45 H38 0.9300 . ? C46 C47 1.374(10) . ? C47 C48 1.433(11) . ? C47 H39 0.9300 . ? C48 C49 1.408(10) . ? C49 C50 1.390(10) . ? C50 C51 1.435(10) . ? C51 C52 1.359(11) . ? C51 H40 0.9300 . ? C53 C54 1.385(10) . ? C53 C54 1.385(10) 2 ? C53 Br3 1.923(11) . ? C54 C55 1.427(13) . ? C54 C65 1.456(11) . ? C55 C56 1.331(13) . ? C55 H41 0.9300 . ? C56 C63 1.423(12) . ? C56 C57 1.524(13) . ? C57 C58 1.473(16) . ? C57 C62 1.519(15) . ? C57 H42 0.9800 . ? C58 C59 1.444(16) . ? C58 H43 0.9700 . ? C58 H44 0.9700 . ? C59 C60 1.489(15) . ? C59 H45 0.9700 . ? C59 H46 0.9700 . ? C60 C63 1.504(13) . ? C60 C61 1.558(15) . ? C60 H47 0.9800 . ? C61 C62 1.386(16) . ? C61 H48 0.9300 . ? C62 H49 0.9300 . ? C63 C64 1.371(12) . ? C64 C65 1.414(12) . ? C64 H50 0.9300 . ? C65 C66 1.403(10) . ? C66 C65 1.403(10) 2 ? C66 C67 1.489(15) . ? C67 C68 1.411(9) 2 ? C67 C68 1.411(9) . ? C68 C69 1.429(11) . ? C68 C79 1.440(10) . ? C69 C70 1.376(12) . ? C69 H51 0.9300 . ? C70 C77 1.426(13) . ? C70 C71 1.514(12) . ? C71 C72 1.493(15) . ? C71 C76 1.570(17) . ? C71 H52 0.9800 . ? C72 C73 1.416(17) . ? C72 H53 0.9700 . ? C72 H54 0.9700 . ? C73 C74 1.555(15) . ? C73 H55 0.9700 . ? C73 H56 0.9700 . ? C74 C75 1.504(16) . ? C74 C77 1.523(11) . ? C74 H57 0.9800 . ? C75 C76 1.410(19) . ? C75 H58 0.9300 . ? C76 H59 0.9300 . ? C77 C78 1.372(12) . ? C78 C79 1.445(10) . ? C78 H60 0.9300 . ? C79 C80 1.381(9) . ? C80 C79 1.381(9) 2 ? C80 Br4 1.895(9) . ? Cl1 C81 1.81(4) . ? Cl2 C81 1.64(4) . ? Cl3 C81 1.66(3) . ? Cl4 C82 1.78(3) . ? Cl4 C84 2.19(5) . ? Cl5 C82 1.75(3) . ? Cl6 C82 1.78(3) . ? O1 C84 1.46(3) . ? O2 C85 1.45(3) . ? O2 C84 1.89(6) . ? C84 C85 1.39(11) . ? O3 C83 1.44(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 112.4(7) . . ? C2 C1 H1 109.1 . . ? C6 C1 H1 109.1 . . ? C2 C1 H2 109.1 . . ? C6 C1 H2 109.1 . . ? H1 C1 H2 107.9 . . ? C1 C2 C3 108.8(7) . . ? C1 C2 H3 109.9 . . ? C3 C2 H3 109.9 . . ? C1 C2 H4 109.9 . . ? C3 C2 H4 109.9 . . ? H3 C2 H4 108.3 . . ? C4 C3 C26 107.5(7) . . ? C4 C3 C2 108.1(7) . . ? C26 C3 C2 105.7(7) . . ? C4 C3 H5 111.8 . . ? C26 C3 H5 111.8 . . ? C2 C3 H5 111.8 . . ? C5 C4 C3 113.2(7) . . ? C5 C4 H6 123.4 . . ? C3 C4 H6 123.4 . . ? C4 C5 C6 113.7(7) . . ? C4 C5 H7 123.2 . . ? C6 C5 H7 123.2 . . ? C7 C6 C1 105.5(7) . . ? C7 C6 C5 106.2(7) . . ? C1 C6 C5 107.3(6) . . ? C7 C6 H8 112.4 . . ? C1 C6 H8 112.4 . . ? C5 C6 H8 112.4 . . ? C8 C7 C26 120.3(7) . . ? C8 C7 C6 126.9(7) . . ? C26 C7 C6 112.8(7) . . ? C7 C8 C9 121.2(7) . . ? C7 C8 H9 119.4 . . ? C9 C8 H9 119.4 . . ? C10 C9 C8 122.8(6) . . ? C10 C9 C24 119.6(6) . . ? C8 C9 C24 117.6(6) . . ? C11 C10 C9 121.2(6) . . ? C11 C10 C49 118.8(6) . . ? C9 C10 C49 120.0(6) . . ? C10 C11 C12 121.4(6) . . ? C10 C11 C22 119.7(6) . . ? C12 C11 C22 118.9(6) . . ? C13 C12 C11 121.0(7) . . ? C13 C12 H10 119.5 . . ? C11 C12 H10 119.5 . . ? C12 C13 C20 119.5(7) . . ? C12 C13 C14 127.3(7) . . ? C20 C13 C14 113.2(7) . . ? C13 C14 C19 106.8(8) . . ? C13 C14 C15 106.5(7) . . ? C19 C14 C15 106.0(7) . . ? C13 C14 H11 112.4 . . ? C19 C14 H11 112.4 . . ? C15 C14 H11 112.4 . . ? C16 C15 C14 110.3(7) . . ? C16 C15 H12 109.6 . . ? C14 C15 H12 109.6 . . ? C16 C15 H13 109.6 . . ? C14 C15 H13 109.6 . . ? H12 C15 H13 108.1 . . ? C15 C16 C17 112.9(7) . . ? C15 C16 H14 109.0 . . ? C17 C16 H14 109.0 . . ? C15 C16 H15 109.0 . . ? C17 C16 H15 109.0 . . ? H14 C16 H15 107.8 . . ? C18 C17 C16 106.2(8) . . ? C18 C17 C20 105.2(7) . . ? C16 C17 C20 108.0(7) . . ? C18 C17 H16 112.3 . . ? C16 C17 H16 112.3 . . ? C20 C17 H16 112.3 . . ? C19 C18 C17 114.2(8) . . ? C19 C18 H17 122.9 . . ? C17 C18 H17 122.9 . . ? C18 C19 C14 111.8(9) . . ? C18 C19 H18 124.1 . . ? C14 C19 H18 124.1 . . ? C21 C20 C13 121.3(7) . . ? C21 C20 C17 127.0(8) . . ? C13 C20 C17 111.7(8) . . ? C20 C21 C22 121.1(7) . . ? C20 C21 H19 119.5 . . ? C22 C21 H19 119.5 . . ? C23 C22 C21 123.9(7) . . ? C23 C22 C11 117.9(6) . . ? C21 C22 C11 118.1(7) . . ? C22 C23 C24 123.9(6) . . ? C22 C23 Br1 118.8(6) . . ? C24 C23 Br1 117.4(6) . . ? C23 C24 C25 123.6(6) . . ? C23 C24 C9 117.5(6) . . ? C25 C24 C9 118.8(7) . . ? C26 C25 C24 121.2(7) . . ? C26 C25 H20 119.4 . . ? C24 C25 H20 119.4 . . ? C25 C26 C7 120.8(7) . . ? C25 C26 C3 127.4(7) . . ? C7 C26 C3 111.7(7) . . ? C28 C27 C32 112.3(8) . . ? C28 C27 H21 109.2 . . ? C32 C27 H21 109.2 . . ? C28 C27 H22 109.2 . . ? C32 C27 H22 109.2 . . ? H21 C27 H22 107.9 . . ? C27 C28 C29 112.0(8) . . ? C27 C28 H23 109.2 . . ? C29 C28 H23 109.2 . . ? C27 C28 H24 109.2 . . ? C29 C28 H24 109.2 . . ? H23 C28 H24 107.9 . . ? C28 C29 C52 105.8(7) . . ? C28 C29 C30 107.6(7) . . ? C52 C29 C30 106.8(7) . . ? C28 C29 H25 112.1 . . ? C52 C29 H25 112.1 . . ? C30 C29 H25 112.1 . . ? C31 C30 C29 112.5(8) . . ? C31 C30 H26 123.7 . . ? C29 C30 H26 123.7 . . ? C30 C31 C32 111.9(8) . . ? C30 C31 H27 124.0 . . ? C32 C31 H27 124.0 . . ? C33 C32 C27 107.1(7) . . ? C33 C32 C31 106.8(7) . . ? C27 C32 C31 106.7(8) . . ? C33 C32 H28 112.0 . . ? C27 C32 H28 112.0 . . ? C31 C32 H28 112.0 . . ? C34 C33 C52 119.7(7) . . ? C34 C33 C32 128.3(7) . . ? C52 C33 C32 112.0(7) . . ? C33 C34 C35 121.9(7) . . ? C33 C34 H29 119.0 . . ? C35 C34 H29 119.0 . . ? C36 C35 C34 124.2(7) . . ? C36 C35 C50 116.5(7) . . ? C34 C35 C50 119.3(7) . . ? C35 C36 C37 123.6(6) . . ? C35 C36 Br2 116.6(6) . . ? C37 C36 Br2 119.7(5) . . ? C36 C37 C38 122.4(7) . . ? C36 C37 C48 117.8(6) . . ? C38 C37 C48 119.8(7) . . ? C39 C38 C37 120.1(7) . . ? C39 C38 H30 119.9 . . ? C37 C38 H30 119.9 . . ? C38 C39 C46 121.0(7) . . ? C38 C39 C40 127.6(8) . . ? C46 C39 C40 111.4(7) . . ? C41 C40 C39 106.9(7) . . ? C41 C40 C45 106.9(8) . . ? C39 C40 C45 105.9(7) . . ? C41 C40 H31 112.3 . . ? C39 C40 H31 112.3 . . ? C45 C40 H31 112.3 . . ? C42 C41 C40 112.8(7) . . ? C42 C41 H32 109.0 . . ? C40 C41 H32 109.0 . . ? C42 C41 H33 109.0 . . ? C40 C41 H33 109.0 . . ? H32 C41 H33 107.8 . . ? C41 C42 C43 111.7(8) . . ? C41 C42 H34 109.3 . . ? C43 C42 H34 109.3 . . ? C41 C42 H35 109.3 . . ? C43 C42 H35 109.3 . . ? H34 C42 H35 107.9 . . ? C46 C43 C42 107.9(7) . . ? C46 C43 C44 106.5(7) . . ? C42 C43 C44 105.1(6) . . ? C46 C43 H36 112.3 . . ? C42 C43 H36 112.3 . . ? C44 C43 H36 112.3 . . ? C45 C44 C43 110.9(8) . . ? C45 C44 H37 124.6 . . ? C43 C44 H37 124.6 . . ? C44 C45 C40 113.8(8) . . ? C44 C45 H38 123.1 . . ? C40 C45 H38 123.1 . . ? C47 C46 C39 119.4(7) . . ? C47 C46 C43 127.5(7) . . ? C39 C46 C43 113.1(7) . . ? C46 C47 C48 121.3(7) . . ? C46 C47 H39 119.3 . . ? C48 C47 H39 119.3 . . ? C49 C48 C37 120.6(7) . . ? C49 C48 C47 121.1(6) . . ? C37 C48 C47 118.2(6) . . ? C50 C49 C48 120.6(6) . . ? C50 C49 C10 119.5(6) . . ? C48 C49 C10 119.9(6) . . ? C49 C50 C51 121.9(6) . . ? C49 C50 C35 120.8(7) . . ? C51 C50 C35 117.3(6) . . ? C52 C51 C50 121.7(7) . . ? C52 C51 H40 119.2 . . ? C50 C51 H40 119.2 . . ? C51 C52 C33 120.1(7) . . ? C51 C52 C29 128.4(7) . . ? C33 C52 C29 111.4(7) . . ? C54 C53 C54 123.1(10) . 2 ? C54 C53 Br3 118.4(5) . . ? C54 C53 Br3 118.4(5) 2 . ? C53 C54 C55 123.4(8) . . ? C53 C54 C65 118.4(8) . . ? C55 C54 C65 118.1(8) . . ? C56 C55 C54 121.6(8) . . ? C56 C55 H41 119.2 . . ? C54 C55 H41 119.2 . . ? C55 C56 C63 121.2(9) . . ? C55 C56 C57 126.9(8) . . ? C63 C56 C57 111.9(8) . . ? C58 C57 C62 106.3(9) . . ? C58 C57 C56 106.2(8) . . ? C62 C57 C56 106.9(8) . . ? C58 C57 H42 112.3 . . ? C62 C57 H42 112.3 . . ? C56 C57 H42 112.3 . . ? C59 C58 C57 112.9(9) . . ? C59 C58 H43 109.0 . . ? C57 C58 H43 109.0 . . ? C59 C58 H44 109.0 . . ? C57 C58 H44 109.0 . . ? H43 C58 H44 107.8 . . ? C58 C59 C60 112.1(9) . . ? C58 C59 H45 109.2 . . ? C60 C59 H45 109.2 . . ? C58 C59 H46 109.2 . . ? C60 C59 H46 109.2 . . ? H45 C59 H46 107.9 . . ? C59 C60 C63 107.1(8) . . ? C59 C60 C61 104.3(8) . . ? C63 C60 C61 106.4(8) . . ? C59 C60 H47 112.8 . . ? C63 C60 H47 112.8 . . ? C61 C60 H47 112.8 . . ? C62 C61 C60 112.8(9) . . ? C62 C61 H48 123.6 . . ? C60 C61 H48 123.6 . . ? C61 C62 C57 112.8(9) . . ? C61 C62 H49 123.6 . . ? C57 C62 H49 123.6 . . ? C64 C63 C56 119.4(8) . . ? C64 C63 C60 127.6(8) . . ? C56 C63 C60 112.9(8) . . ? C63 C64 C65 121.8(8) . . ? C63 C64 H50 119.1 . . ? C65 C64 H50 119.1 . . ? C66 C65 C64 122.7(8) . . ? C66 C65 C54 119.6(8) . . ? C64 C65 C54 117.7(7) . . ? C65 C66 C65 120.7(10) . 2 ? C65 C66 C67 119.6(5) . . ? C65 C66 C67 119.6(5) 2 . ? C68 C67 C68 120.0(9) 2 . ? C68 C67 C66 120.0(5) 2 . ? C68 C67 C66 120.0(5) . . ? C67 C68 C69 121.1(7) . . ? C67 C68 C79 119.8(7) . . ? C69 C68 C79 119.1(7) . . ? C70 C69 C68 121.2(7) . . ? C70 C69 H51 119.4 . . ? C68 C69 H51 119.4 . . ? C69 C70 C77 120.1(7) . . ? C69 C70 C71 127.0(9) . . ? C77 C70 C71 112.9(8) . . ? C72 C71 C70 108.0(9) . . ? C72 C71 C76 105.6(9) . . ? C70 C71 C76 105.2(8) . . ? C72 C71 H52 112.5 . . ? C70 C71 H52 112.5 . . ? C76 C71 H52 112.5 . . ? C73 C72 C71 113.0(10) . . ? C73 C72 H53 109.0 . . ? C71 C72 H53 109.0 . . ? C73 C72 H54 109.0 . . ? C71 C72 H54 109.0 . . ? H53 C72 H54 107.8 . . ? C72 C73 C74 112.9(10) . . ? C72 C73 H55 109.0 . . ? C74 C73 H55 109.0 . . ? C72 C73 H56 109.0 . . ? C74 C73 H56 109.0 . . ? H55 C73 H56 107.8 . . ? C75 C74 C77 106.1(8) . . ? C75 C74 C73 103.6(9) . . ? C77 C74 C73 106.4(8) . . ? C75 C74 H57 113.3 . . ? C77 C74 H57 113.3 . . ? C73 C74 H57 113.3 . . ? C76 C75 C74 115.0(10) . . ? C76 C75 H58 122.5 . . ? C74 C75 H58 122.5 . . ? C75 C76 C71 110.9(10) . . ? C75 C76 H59 124.6 . . ? C71 C76 H59 124.6 . . ? C78 C77 C70 120.5(7) . . ? C78 C77 C74 126.6(8) . . ? C70 C77 C74 112.8(8) . . ? C77 C78 C79 121.2(7) . . ? C77 C78 H60 119.4 . . ? C79 C78 H60 119.4 . . ? C80 C79 C68 118.4(7) . . ? C80 C79 C78 123.7(7) . . ? C68 C79 C78 117.9(7) . . ? C79 C80 C79 123.6(9) 2 . ? C79 C80 Br4 118.2(4) 2 . ? C79 C80 Br4 118.2(4) . . ? Cl3 C81 Cl2 117(2) . . ? Cl3 C81 Cl1 104.5(19) . . ? Cl2 C81 Cl1 116.0(19) . . ? C82 Cl4 C84 154.3(19) . . ? Cl5 C82 Cl4 117(2) . . ? Cl5 C82 Cl6 115(2) . . ? Cl4 C82 Cl6 116(2) . . ? C85 O2 C84 47(5) . . ? O1 C84 C85 82(4) . . ? O1 C84 O2 129(4) . . ? C85 C84 O2 50(2) . . ? O1 C84 Cl4 123(3) . . ? C85 C84 Cl4 115(4) . . ? O2 C84 Cl4 74(2) . . ? O2 C85 C84 84(5) . . ? 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 C6 C1 C2 C3 -1.6(9) . . . . ? C1 C2 C3 C4 -55.7(8) . . . . ? C1 C2 C3 C26 59.1(9) . . . . ? C26 C3 C4 C5 -54.5(9) . . . . ? C2 C3 C4 C5 59.1(9) . . . . ? C3 C4 C5 C6 -2.5(10) . . . . ? C2 C1 C6 C7 -57.5(8) . . . . ? C2 C1 C6 C5 55.5(9) . . . . ? C4 C5 C6 C7 57.1(9) . . . . ? C4 C5 C6 C1 -55.4(9) . . . . ? C1 C6 C7 C8 -118.1(8) . . . . ? C5 C6 C7 C8 128.1(8) . . . . ? C1 C6 C7 C26 60.9(8) . . . . ? C5 C6 C7 C26 -52.8(9) . . . . ? C26 C7 C8 C9 -4.0(11) . . . . ? C6 C7 C8 C9 174.9(7) . . . . ? C7 C8 C9 C10 -175.2(7) . . . . ? C7 C8 C9 C24 3.4(10) . . . . ? C8 C9 C10 C11 174.3(6) . . . . ? C24 C9 C10 C11 -4.2(10) . . . . ? C8 C9 C10 C49 -2.9(10) . . . . ? C24 C9 C10 C49 178.6(6) . . . . ? C9 C10 C11 C12 -177.1(6) . . . . ? C49 C10 C11 C12 0.2(10) . . . . ? C9 C10 C11 C22 1.2(10) . . . . ? C49 C10 C11 C22 178.5(6) . . . . ? C10 C11 C12 C13 178.5(7) . . . . ? C22 C11 C12 C13 0.1(10) . . . . ? C11 C12 C13 C20 0.0(11) . . . . ? C11 C12 C13 C14 179.1(7) . . . . ? C12 C13 C14 C19 -124.5(9) . . . . ? C20 C13 C14 C19 54.7(9) . . . . ? C12 C13 C14 C15 122.7(9) . . . . ? C20 C13 C14 C15 -58.2(9) . . . . ? C13 C14 C15 C16 57.8(9) . . . . ? C19 C14 C15 C16 -55.7(10) . . . . ? C14 C15 C16 C17 -1.4(10) . . . . ? C15 C16 C17 C18 57.4(9) . . . . ? C15 C16 C17 C20 -55.0(10) . . . . ? C16 C17 C18 C19 -56.8(10) . . . . ? C20 C17 C18 C19 57.6(11) . . . . ? C17 C18 C19 C14 -1.4(12) . . . . ? C13 C14 C19 C18 -55.3(10) . . . . ? C15 C14 C19 C18 57.9(11) . . . . ? C12 C13 C20 C21 -0.5(12) . . . . ? C14 C13 C20 C21 -179.7(7) . . . . ? C12 C13 C20 C17 -179.0(7) . . . . ? C14 C13 C20 C17 1.8(10) . . . . ? C18 C17 C20 C21 124.1(10) . . . . ? C16 C17 C20 C21 -122.7(9) . . . . ? C18 C17 C20 C13 -57.4(9) . . . . ? C16 C17 C20 C13 55.7(10) . . . . ? C13 C20 C21 C22 0.8(11) . . . . ? C17 C20 C21 C22 179.1(7) . . . . ? C20 C21 C22 C23 178.2(7) . . . . ? C20 C21 C22 C11 -0.6(10) . . . . ? C10 C11 C22 C23 2.9(10) . . . . ? C12 C11 C22 C23 -178.8(6) . . . . ? C10 C11 C22 C21 -178.2(6) . . . . ? C12 C11 C22 C21 0.2(9) . . . . ? C21 C22 C23 C24 177.1(7) . . . . ? C11 C22 C23 C24 -4.1(10) . . . . ? C21 C22 C23 Br1 -3.0(10) . . . . ? C11 C22 C23 Br1 175.9(5) . . . . ? C22 C23 C24 C25 -174.5(7) . . . . ? Br1 C23 C24 C25 5.6(9) . . . . ? C22 C23 C24 C9 1.1(10) . . . . ? Br1 C23 C24 C9 -178.8(5) . . . . ? C10 C9 C24 C23 3.1(9) . . . . ? C8 C9 C24 C23 -175.5(6) . . . . ? C10 C9 C24 C25 178.9(6) . . . . ? C8 C9 C24 C25 0.3(9) . . . . ? C23 C24 C25 C26 172.2(7) . . . . ? C9 C24 C25 C26 -3.3(10) . . . . ? C24 C25 C26 C7 2.9(11) . . . . ? C24 C25 C26 C3 -172.5(7) . . . . ? C8 C7 C26 C25 0.9(11) . . . . ? C6 C7 C26 C25 -178.2(7) . . . . ? C8 C7 C26 C3 176.9(7) . . . . ? C6 C7 C26 C3 -2.2(9) . . . . ? C4 C3 C26 C25 -127.1(9) . . . . ? C2 C3 C26 C25 117.7(9) . . . . ? C4 C3 C26 C7 57.3(9) . . . . ? C2 C3 C26 C7 -58.0(9) . . . . ? C32 C27 C28 C29 0.9(10) . . . . ? C27 C28 C29 C52 -58.0(9) . . . . ? C27 C28 C29 C30 55.9(9) . . . . ? C28 C29 C30 C31 -55.4(10) . . . . ? C52 C29 C30 C31 57.8(10) . . . . ? C29 C30 C31 C32 -1.0(11) . . . . ? C28 C27 C32 C33 57.1(10) . . . . ? C28 C27 C32 C31 -57.0(9) . . . . ? C30 C31 C32 C33 -56.7(10) . . . . ? C30 C31 C32 C27 57.5(9) . . . . ? C27 C32 C33 C34 120.0(9) . . . . ? C31 C32 C33 C34 -126.1(9) . . . . ? C27 C32 C33 C52 -57.1(9) . . . . ? C31 C32 C33 C52 56.9(9) . . . . ? C52 C33 C34 C35 1.5(11) . . . . ? C32 C33 C34 C35 -175.4(7) . . . . ? C33 C34 C35 C36 176.0(7) . . . . ? C33 C34 C35 C50 -2.2(11) . . . . ? C34 C35 C36 C37 -177.8(7) . . . . ? C50 C35 C36 C37 0.5(10) . . . . ? C34 C35 C36 Br2 -0.7(10) . . . . ? C50 C35 C36 Br2 177.6(5) . . . . ? C35 C36 C37 C38 177.4(7) . . . . ? Br2 C36 C37 C38 0.4(10) . . . . ? C35 C36 C37 C48 -1.3(11) . . . . ? Br2 C36 C37 C48 -178.3(5) . . . . ? C36 C37 C38 C39 -179.5(7) . . . . ? C48 C37 C38 C39 -0.8(11) . . . . ? C37 C38 C39 C46 -0.5(12) . . . . ? C37 C38 C39 C40 178.9(7) . . . . ? C38 C39 C40 C41 123.5(9) . . . . ? C46 C39 C40 C41 -57.1(9) . . . . ? C38 C39 C40 C45 -122.8(9) . . . . ? C46 C39 C40 C45 56.6(9) . . . . ? C39 C40 C41 C42 59.4(10) . . . . ? C45 C40 C41 C42 -53.6(9) . . . . ? C40 C41 C42 C43 -4.2(11) . . . . ? C41 C42 C43 C46 -53.0(9) . . . . ? C41 C42 C43 C44 60.3(9) . . . . ? C46 C43 C44 C45 57.3(9) . . . . ? C42 C43 C44 C45 -57.0(9) . . . . ? C43 C44 C45 C40 -0.3(11) . . . . ? C41 C40 C45 C44 57.0(10) . . . . ? C39 C40 C45 C44 -56.7(10) . . . . ? C38 C39 C46 C47 0.6(12) . . . . ? C40 C39 C46 C47 -178.9(7) . . . . ? C38 C39 C46 C43 179.2(7) . . . . ? C40 C39 C46 C43 -0.3(10) . . . . ? C42 C43 C46 C47 -126.4(8) . . . . ? C44 C43 C46 C47 121.2(8) . . . . ? C42 C43 C46 C39 55.2(9) . . . . ? C44 C43 C46 C39 -57.2(9) . . . . ? C39 C46 C47 C48 0.5(11) . . . . ? C43 C46 C47 C48 -177.8(7) . . . . ? C36 C37 C48 C49 0.8(10) . . . . ? C38 C37 C48 C49 -177.9(6) . . . . ? C36 C37 C48 C47 -179.4(6) . . . . ? C38 C37 C48 C47 1.9(10) . . . . ? C46 C47 C48 C49 178.1(7) . . . . ? C46 C47 C48 C37 -1.7(10) . . . . ? C37 C48 C49 C50 0.4(10) . . . . ? C47 C48 C49 C50 -179.4(6) . . . . ? C37 C48 C49 C10 -177.4(6) . . . . ? C47 C48 C49 C10 2.8(10) . . . . ? C11 C10 C49 C50 -83.5(8) . . . . ? C9 C10 C49 C50 93.8(8) . . . . ? C11 C10 C49 C48 94.3(8) . . . . ? C9 C10 C49 C48 -88.4(8) . . . . ? C48 C49 C50 C51 176.0(6) . . . . ? C10 C49 C50 C51 -6.2(10) . . . . ? C48 C49 C50 C35 -1.2(10) . . . . ? C10 C49 C50 C35 176.6(6) . . . . ? C36 C35 C50 C49 0.8(10) . . . . ? C34 C35 C50 C49 179.2(7) . . . . ? C36 C35 C50 C51 -176.6(6) . . . . ? C34 C35 C50 C51 1.8(10) . . . . ? C49 C50 C51 C52 -178.1(7) . . . . ? C35 C50 C51 C52 -0.8(10) . . . . ? C50 C51 C52 C33 0.0(11) . . . . ? C50 C51 C52 C29 177.1(7) . . . . ? C34 C33 C52 C51 -0.3(11) . . . . ? C32 C33 C52 C51 177.0(7) . . . . ? C34 C33 C52 C29 -177.9(7) . . . . ? C32 C33 C52 C29 -0.5(9) . . . . ? C28 C29 C52 C51 -119.8(9) . . . . ? C30 C29 C52 C51 125.8(8) . . . . ? C28 C29 C52 C33 57.5(8) . . . . ? C30 C29 C52 C33 -57.0(8) . . . . ? C54 C53 C54 C55 -177.5(11) 2 . . . ? Br3 C53 C54 C55 2.5(11) . . . . ? C54 C53 C54 C65 1.8(6) 2 . . . ? Br3 C53 C54 C65 -178.2(6) . . . . ? C53 C54 C55 C56 -177.5(8) . . . . ? C65 C54 C55 C56 3.3(15) . . . . ? C54 C55 C56 C63 0.2(16) . . . . ? C54 C55 C56 C57 178.9(10) . . . . ? C55 C56 C57 C58 124.3(11) . . . . ? C63 C56 C57 C58 -57.0(11) . . . . ? C55 C56 C57 C62 -122.5(11) . . . . ? C63 C56 C57 C62 56.3(11) . . . . ? C62 C57 C58 C59 -56.3(12) . . . . ? C56 C57 C58 C59 57.4(12) . . . . ? C57 C58 C59 C60 -1.5(14) . . . . ? C58 C59 C60 C63 -55.2(11) . . . . ? C58 C59 C60 C61 57.3(11) . . . . ? C59 C60 C61 C62 -57.7(11) . . . . ? C63 C60 C61 C62 55.4(11) . . . . ? C60 C61 C62 C57 1.0(13) . . . . ? C58 C57 C62 C61 56.3(12) . . . . ? C56 C57 C62 C61 -56.9(11) . . . . ? C55 C56 C63 C64 -3.6(14) . . . . ? C57 C56 C63 C64 177.5(8) . . . . ? C55 C56 C63 C60 179.5(9) . . . . ? C57 C56 C63 C60 0.6(12) . . . . ? C59 C60 C63 C64 -121.0(10) . . . . ? C61 C60 C63 C64 127.8(10) . . . . ? C59 C60 C63 C56 55.5(10) . . . . ? C61 C60 C63 C56 -55.6(10) . . . . ? C56 C63 C64 C65 3.4(13) . . . . ? C60 C63 C64 C65 179.8(9) . . . . ? C63 C64 C65 C66 -179.0(7) . . . . ? C63 C64 C65 C54 0.0(13) . . . . ? C53 C54 C65 C66 -3.6(11) . . . . ? C55 C54 C65 C66 175.7(7) . . . . ? C53 C54 C65 C64 177.3(7) . . . . ? C55 C54 C65 C64 -3.4(13) . . . . ? C64 C65 C66 C65 -179.2(9) . . . 2 ? C54 C65 C66 C65 1.8(6) . . . 2 ? C64 C65 C66 C67 0.8(9) . . . . ? C54 C65 C66 C67 -178.2(6) . . . . ? C65 C66 C67 C68 87.1(5) . . . 2 ? C65 C66 C67 C68 -92.9(5) 2 . . 2 ? C65 C66 C67 C68 -92.9(5) . . . . ? C65 C66 C67 C68 87.1(5) 2 . . . ? C68 C67 C68 C69 179.5(8) 2 . . . ? C66 C67 C68 C69 -0.5(8) . . . . ? C68 C67 C68 C79 -0.3(4) 2 . . . ? C66 C67 C68 C79 179.7(4) . . . . ? C67 C68 C69 C70 179.1(7) . . . . ? C79 C68 C69 C70 -1.2(12) . . . . ? C68 C69 C70 C77 0.6(13) . . . . ? C68 C69 C70 C71 177.5(8) . . . . ? C69 C70 C71 C72 127.1(11) . . . . ? C77 C70 C71 C72 -55.8(11) . . . . ? C69 C70 C71 C76 -120.5(11) . . . . ? C77 C70 C71 C76 56.6(11) . . . . ? C70 C71 C72 C73 55.9(12) . . . . ? C76 C71 C72 C73 -56.2(11) . . . . ? C71 C72 C73 C74 -0.6(12) . . . . ? C72 C73 C74 C75 57.4(10) . . . . ? C72 C73 C74 C77 -54.2(11) . . . . ? C77 C74 C75 C76 54.8(12) . . . . ? C73 C74 C75 C76 -57.1(11) . . . . ? C74 C75 C76 C71 1.7(12) . . . . ? C72 C71 C76 C75 56.5(11) . . . . ? C70 C71 C76 C75 -57.6(11) . . . . ? C69 C70 C77 C78 -0.2(13) . . . . ? C71 C70 C77 C78 -177.5(8) . . . . ? C69 C70 C77 C74 176.8(8) . . . . ? C71 C70 C77 C74 -0.5(11) . . . . ? C75 C74 C77 C78 121.1(10) . . . . ? C73 C74 C77 C78 -129.1(10) . . . . ? C75 C74 C77 C70 -55.7(11) . . . . ? C73 C74 C77 C70 54.2(11) . . . . ? C70 C77 C78 C79 0.4(11) . . . . ? C74 C77 C78 C79 -176.2(8) . . . . ? C67 C68 C79 C80 0.5(9) . . . . ? C69 C68 C79 C80 -179.2(6) . . . . ? C67 C68 C79 C78 -179.0(5) . . . . ? C69 C68 C79 C78 1.3(10) . . . . ? C77 C78 C79 C80 179.6(6) . . . . ? C77 C78 C79 C68 -0.9(10) . . . . ? C68 C79 C80 C79 -0.3(4) . . . 2 ? C78 C79 C80 C79 179.2(7) . . . 2 ? C68 C79 C80 Br4 179.7(4) . . . . ? C78 C79 C80 Br4 -0.8(7) . . . . ? C84 Cl4 C82 Cl5 171(3) . . . . ? C84 Cl4 C82 Cl6 30(10) . . . . ? C85 O2 C84 O1 -24(6) . . . . ? C85 O2 C84 Cl4 -144(6) . . . . ? C82 Cl4 C84 O1 -117(7) . . . . ? C82 Cl4 C84 C85 -20(8) . . . . ? C82 Cl4 C84 O2 10(7) . . . . ? O1 C84 C85 O2 162(5) . . . . ? Cl4 C84 C85 O2 39(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.733 _refine_diff_density_min -1.358 _refine_diff_density_rms 0.182 _database_code_depnum_ccdc_archive 'CCDC 923856' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl7 #TrackingRef '9PCF3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C60 H30 F12' _chemical_formula_sum 'C60 H30 F12' _chemical_formula_weight 978.84 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _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 13.271(10) _cell_length_b 30.35(2) _cell_length_c 12.823(10) _cell_angle_alpha 90.00 _cell_angle_beta 121.152(11) _cell_angle_gamma 90.00 _cell_volume 4420(6) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 574 _cell_measurement_theta_min 9.08 _cell_measurement_theta_max 25.31 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1992 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.9869 _exptl_absorpt_correction_T_max 0.9976 _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25074 _diffrn_reflns_av_R_equivalents 0.1214 _diffrn_reflns_av_sigmaI/netI 0.0929 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 23.49 _reflns_number_total 3255 _reflns_number_gt 1272 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1500P)^2^+1.5564P] 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 3255 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2213 _refine_ls_R_factor_gt 0.1051 _refine_ls_wR_factor_ref 0.3304 _refine_ls_wR_factor_gt 0.2478 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.5939(5) 0.1018(2) 0.5717(6) 0.204(3) Uani 1 1 d . A . F2 F 0.5086(7) 0.0448(5) 0.4968(14) 0.155(6) Uani 0.72(2) 1 d P A 3 F3 F 0.5793(6) 0.0837(4) 0.4185(8) 0.144(5) Uani 0.72(2) 1 d P A 3 F4 F 0.0865(8) 0.1678(3) 0.4128(7) 0.142(5) Uani 0.646(13) 1 d P A 1 F5 F 0.2385(14) 0.2071(5) 0.5002(15) 0.150(4) Uani 0.646(13) 1 d P A 1 F6 F 0.2335(9) 0.1467(3) 0.5777(6) 0.134(4) Uani 0.646(13) 1 d P A 1 C1 C 0.4490(7) 0.2290(3) 0.0726(6) 0.118(3) Uani 1 1 d . . . H1 H 0.4905 0.2317 0.1588 0.142 Uiso 1 1 calc R . . C2 C 0.4891(8) 0.2487(3) 0.0122(7) 0.130(3) Uani 1 1 d . . . H2 H 0.5613 0.2645 0.0545 0.156 Uiso 1 1 calc R . . C3 C 0.4230(8) 0.2469(3) -0.1229(6) 0.136(3) Uani 1 1 d . . . H3 H 0.4530 0.2615 -0.1669 0.163 Uiso 1 1 calc R . . C4 C 0.3252(7) 0.2257(3) -0.1806(6) 0.107(2) Uani 1 1 d . . . H4 H 0.2827 0.2259 -0.2671 0.128 Uiso 1 1 calc R . . C5 C 0.2793(7) 0.2025(3) -0.1207(6) 0.107(2) Uani 1 1 d . . . C6 C 0.1793(7) 0.1774(3) -0.1792(5) 0.098(2) Uani 1 1 d . . . H6 H 0.1370 0.1772 -0.2658 0.118 Uiso 1 1 calc R . . C7 C 0.1339(6) 0.1514(2) -0.1193(5) 0.089(2) Uani 1 1 d . . . C8 C 0.0330(6) 0.1249(2) -0.1819(5) 0.089(2) Uani 1 1 d . . . C9 C -0.0041(6) 0.0991(3) -0.1193(5) 0.094(2) Uani 1 1 d . . . C10 C -0.1075(6) 0.0732(3) -0.1806(5) 0.099(2) Uani 1 1 d . . . H10 H -0.1501 0.0728 -0.2672 0.119 Uiso 1 1 calc R . . C11 C -0.1493(7) 0.0484(3) -0.1203(5) 0.101(2) Uani 1 1 d . . . C12 C -0.2563(6) 0.0249(3) -0.1796(6) 0.106(2) Uani 1 1 d . . . H12 H -0.3004 0.0250 -0.2661 0.127 Uiso 1 1 calc R . . C13 C -0.2992(7) 0.0029(3) -0.1226(6) 0.134(3) Uani 1 1 d . . . H13 H -0.3735 -0.0113 -0.1672 0.161 Uiso 1 1 calc R . . C14 C -0.2308(8) 0.0006(3) 0.0097(6) 0.127(3) Uani 1 1 d . . . H14 H -0.2589 -0.0157 0.0529 0.153 Uiso 1 1 calc R . . C15 C -0.1285(7) 0.0217(3) 0.0690(6) 0.120(3) Uani 1 1 d . . . H15 H -0.0840 0.0191 0.1552 0.145 Uiso 1 1 calc R . . C16 C -0.0796(7) 0.0484(2) 0.0119(5) 0.093(2) Uani 1 1 d . . . C17 C 0.0214(6) 0.0708(3) 0.0721(5) 0.096(2) Uani 1 1 d . . . H17 H 0.0677 0.0676 0.1581 0.116 Uiso 1 1 calc R . . C18 C 0.0636(6) 0.0991(3) 0.0150(5) 0.093(2) Uani 1 1 d . . . C19 C 0.1635(6) 0.1248(3) 0.0772(5) 0.089(2) Uani 1 1 d . . . C20 C 0.2014(6) 0.1509(2) 0.0142(5) 0.088(2) Uani 1 1 d . . . C21 C 0.3012(6) 0.1791(3) 0.0721(5) 0.101(2) Uani 1 1 d . . . H21 H 0.3415 0.1815 0.1584 0.122 Uiso 1 1 calc R . . C22 C 0.3430(7) 0.2028(3) 0.0127(5) 0.096(2) Uani 1 1 d . . . C23 C 0.2314(6) 0.1249(3) 0.2126(5) 0.091(2) Uani 1 1 d . A . C24 C 0.3364(7) 0.1039(3) 0.2769(5) 0.109(3) Uani 1 1 d . . . H24 H 0.3667 0.0885 0.2346 0.131 Uiso 1 1 calc R . . C25 C 0.4007(6) 0.1046(3) 0.4040(5) 0.103(2) Uani 1 1 d . A . C26 C 0.5227(15) 0.0813(6) 0.4691(8) 0.136(4) Uani 1 1 d . . . C27 C 0.3569(7) 0.1253(3) 0.4655(5) 0.098(2) Uani 1 1 d . . . H27 H 0.4003 0.1251 0.5521 0.118 Uiso 1 1 calc R A . C28 C 0.2518(7) 0.1465(3) 0.4049(5) 0.103(2) Uani 1 1 d . A . C29 C 0.2064(16) 0.1691(7) 0.4708(9) 0.152(5) Uani 1 1 d . . . C30 C 0.1899(6) 0.1468(3) 0.2776(5) 0.107(2) Uani 1 1 d . . . H30 H 0.1176 0.1625 0.2346 0.128 Uiso 1 1 calc R A . F10 F 0.509(2) 0.0523(10) 0.570(2) 0.141(10) Uani 0.28(2) 1 d P A 4 F7 F 0.1600(19) 0.2163(6) 0.407(2) 0.163(8) Uiso 0.354(13) 1 d P A 2 F11 F 0.498(2) 0.0359(8) 0.4018(18) 0.158(13) Uani 0.28(2) 1 d P A 4 F8 F 0.3110(18) 0.1961(9) 0.5641(17) 0.152(9) Uani 0.354(13) 1 d P A 2 F9 F 0.154(3) 0.1601(9) 0.497(3) 0.171(11) Uiso 0.354(13) 1 d P A 2 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 F1 0.152(5) 0.247(7) 0.119(5) 0.024(5) 0.003(4) 0.002(5) F2 0.111(5) 0.182(10) 0.119(16) 0.029(12) 0.022(7) -0.003(6) F3 0.100(5) 0.214(11) 0.101(6) 0.027(5) 0.040(4) 0.035(5) F4 0.117(7) 0.230(10) 0.068(5) -0.021(5) 0.038(4) 0.033(6) F5 0.167(13) 0.160(10) 0.133(13) -0.005(10) 0.086(12) 0.028(10) F6 0.170(7) 0.192(9) 0.050(4) 0.013(4) 0.064(4) 0.026(6) C1 0.133(7) 0.164(8) 0.046(4) -0.007(4) 0.038(4) -0.032(6) C2 0.139(6) 0.173(9) 0.068(5) -0.024(5) 0.046(5) -0.038(6) C3 0.150(7) 0.184(9) 0.057(5) -0.007(5) 0.042(5) -0.041(7) C4 0.129(6) 0.136(7) 0.042(4) -0.007(4) 0.035(4) -0.043(5) C5 0.101(5) 0.144(7) 0.046(4) -0.013(4) 0.016(4) -0.016(5) C6 0.117(6) 0.132(6) 0.043(3) 0.009(4) 0.040(4) 0.019(5) C7 0.097(5) 0.115(5) 0.037(3) -0.004(3) 0.022(3) 0.006(4) C8 0.095(5) 0.121(6) 0.033(3) -0.002(4) 0.019(3) -0.002(4) C9 0.099(5) 0.129(6) 0.038(3) -0.001(4) 0.024(3) 0.009(5) C10 0.108(5) 0.127(6) 0.038(3) 0.005(4) 0.020(4) 0.007(5) C11 0.113(5) 0.133(6) 0.036(3) 0.009(4) 0.023(4) 0.003(5) C12 0.105(5) 0.138(7) 0.042(4) 0.000(4) 0.015(4) -0.029(5) C13 0.138(7) 0.184(9) 0.051(4) 0.010(5) 0.028(4) -0.044(6) C14 0.125(6) 0.156(8) 0.067(5) 0.020(5) 0.026(5) -0.032(6) C15 0.128(6) 0.146(7) 0.045(4) 0.009(4) 0.015(4) -0.006(6) C16 0.111(5) 0.106(5) 0.046(4) 0.011(4) 0.030(4) -0.001(4) C17 0.104(5) 0.130(6) 0.038(3) 0.001(4) 0.024(4) -0.005(5) C18 0.099(5) 0.134(6) 0.036(3) 0.007(4) 0.027(3) 0.005(5) C19 0.084(4) 0.124(6) 0.043(3) 0.001(4) 0.022(3) 0.005(4) C20 0.089(5) 0.109(5) 0.040(3) -0.006(4) 0.014(3) -0.002(4) C21 0.107(5) 0.147(7) 0.035(3) -0.006(4) 0.027(4) 0.005(5) C22 0.112(5) 0.118(6) 0.044(4) 0.004(4) 0.029(4) 0.007(5) C23 0.091(5) 0.131(6) 0.033(3) 0.003(4) 0.019(3) 0.003(4) C24 0.115(5) 0.153(7) 0.040(3) 0.001(4) 0.026(4) 0.004(5) C25 0.104(5) 0.139(7) 0.042(3) -0.001(4) 0.021(4) 0.006(5) C26 0.180(13) 0.159(12) 0.042(5) 0.011(7) 0.038(6) 0.024(10) C27 0.108(6) 0.137(6) 0.033(3) 0.005(4) 0.025(4) -0.001(5) C28 0.109(5) 0.140(7) 0.039(3) -0.004(4) 0.023(4) -0.001(5) C29 0.177(16) 0.203(16) 0.056(6) -0.042(7) 0.046(8) 0.012(11) C30 0.105(5) 0.148(7) 0.048(4) 0.003(4) 0.027(4) 0.020(5) F10 0.173(18) 0.19(2) 0.052(10) 0.072(13) 0.054(12) 0.067(16) F11 0.170(18) 0.19(2) 0.029(10) -0.007(10) -0.007(9) 0.079(17) F8 0.135(15) 0.20(2) 0.096(13) -0.031(12) 0.041(10) 0.031(14) _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 F1 C26 1.313(12) . ? F2 C26 1.206(14) . ? F3 C26 1.223(15) . ? F4 C29 1.365(18) . ? F5 C29 1.218(17) . ? F6 C29 1.401(17) . ? C1 C2 1.292(9) . ? C1 C22 1.443(9) . ? C1 H1 0.9500 . ? C2 C3 1.484(10) . ? C2 H2 0.9500 . ? C3 C4 1.286(9) . ? C3 H3 0.9500 . ? C4 C5 1.392(9) . ? C4 H4 0.9500 . ? C5 C6 1.369(9) . ? C5 C22 1.465(9) . ? C6 C7 1.434(9) . ? C6 H6 0.9500 . ? C7 C8 1.404(9) . ? C7 C20 1.465(8) . ? C8 C9 1.382(9) . ? C8 C8 1.496(10) 2_554 ? C9 C10 1.416(9) . ? C9 C18 1.474(8) . ? C10 C11 1.384(9) . ? C10 H10 0.9500 . ? C11 C12 1.409(9) . ? C11 C16 1.451(8) . ? C12 C13 1.317(9) . ? C12 H12 0.9500 . ? C13 C14 1.453(9) . ? C13 H13 0.9500 . ? C14 C15 1.328(9) . ? C14 H14 0.9500 . ? C15 C16 1.452(10) . ? C15 H15 0.9500 . ? C16 C17 1.336(9) . ? C17 C18 1.418(9) . ? C17 H17 0.9500 . ? C18 C19 1.381(9) . ? C19 C20 1.398(9) . ? C19 C23 1.485(8) . ? C20 C21 1.421(9) . ? C21 C22 1.357(9) . ? C21 H21 0.9500 . ? C23 C24 1.356(9) . ? C23 C30 1.384(9) . ? C24 C25 1.396(8) . ? C24 H24 0.9500 . ? C25 C27 1.352(9) . ? C25 C26 1.556(14) . ? C26 F11 1.57(3) . ? C26 F10 1.65(2) . ? C27 C28 1.357(9) . ? C27 H27 0.9500 . ? C28 C30 1.397(8) . ? C28 C29 1.440(13) . ? C29 F9 0.96(2) . ? C29 F8 1.52(3) . ? C29 F7 1.61(3) . ? C30 H30 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C22 121.8(7) . . ? C2 C1 H1 119.1 . . ? C22 C1 H1 119.1 . . ? C1 C2 C3 120.3(8) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.0(8) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 122.4(7) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C6 C5 C4 123.8(6) . . ? C6 C5 C22 116.9(7) . . ? C4 C5 C22 119.2(7) . . ? C5 C6 C7 124.7(6) . . ? C5 C6 H6 117.6 . . ? C7 C6 H6 117.6 . . ? C8 C7 C6 123.4(6) . . ? C8 C7 C20 119.2(6) . . ? C6 C7 C20 117.3(6) . . ? C9 C8 C7 120.9(5) . . ? C9 C8 C8 120.6(6) . 2_554 ? C7 C8 C8 118.5(6) . 2_554 ? C8 C9 C10 121.8(6) . . ? C8 C9 C18 119.6(7) . . ? C10 C9 C18 118.6(7) . . ? C11 C10 C9 123.0(6) . . ? C11 C10 H10 118.5 . . ? C9 C10 H10 118.5 . . ? C10 C11 C12 123.8(6) . . ? C10 C11 C16 117.1(7) . . ? C12 C11 C16 119.0(7) . . ? C13 C12 C11 124.2(6) . . ? C13 C12 H12 117.9 . . ? C11 C12 H12 117.9 . . ? C12 C13 C14 118.9(7) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 118.8(7) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 124.9(7) . . ? C14 C15 H15 117.6 . . ? C16 C15 H15 117.6 . . ? C17 C16 C11 121.2(7) . . ? C17 C16 C15 124.7(6) . . ? C11 C16 C15 114.1(7) . . ? C16 C17 C18 123.8(6) . . ? C16 C17 H17 118.1 . . ? C18 C17 H17 118.1 . . ? C19 C18 C17 124.1(6) . . ? C19 C18 C9 119.8(6) . . ? C17 C18 C9 116.0(6) . . ? C18 C19 C20 120.7(5) . . ? C18 C19 C23 119.8(6) . . ? C20 C19 C23 119.5(6) . . ? C19 C20 C21 123.8(6) . . ? C19 C20 C7 119.7(6) . . ? C21 C20 C7 116.5(6) . . ? C22 C21 C20 124.5(6) . . ? C22 C21 H21 117.7 . . ? C20 C21 H21 117.7 . . ? C21 C22 C1 124.2(6) . . ? C21 C22 C5 119.7(7) . . ? C1 C22 C5 116.0(7) . . ? C24 C23 C30 117.6(5) . . ? C24 C23 C19 121.4(6) . . ? C30 C23 C19 121.0(6) . . ? C23 C24 C25 121.3(7) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C27 C25 C24 120.0(7) . . ? C27 C25 C26 122.7(7) . . ? C24 C25 C26 117.3(8) . . ? F2 C26 F3 116.3(14) . . ? F2 C26 F1 106.3(10) . . ? F3 C26 F1 100.5(18) . . ? F2 C26 C25 107.3(16) . . ? F3 C26 C25 116.3(9) . . ? F1 C26 C25 109.4(9) . . ? F2 C26 F11 48.3(16) . . ? F3 C26 F11 76.8(12) . . ? F1 C26 F11 143.6(11) . . ? C25 C26 F11 103.9(11) . . ? F2 C26 F10 35.4(14) . . ? F3 C26 F10 142.6(13) . . ? F1 C26 F10 77.2(10) . . ? C25 C26 F10 99.1(14) . . ? F11 C26 F10 84(2) . . ? C25 C27 C28 120.7(6) . . ? C25 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C27 C28 C30 118.8(7) . . ? C27 C28 C29 120.5(7) . . ? C30 C28 C29 120.7(8) . . ? F9 C29 F5 111(2) . . ? F9 C29 F4 48(3) . . ? F5 C29 F4 108.7(15) . . ? F9 C29 F6 52(2) . . ? F5 C29 F6 106.5(9) . . ? F4 C29 F6 98.9(15) . . ? F9 C29 C28 132(3) . . ? F5 C29 C28 116.5(18) . . ? F4 C29 C28 112.9(9) . . ? F6 C29 C28 111.7(12) . . ? F9 C29 F8 114(2) . . ? F5 C29 F8 38.4(11) . . ? F4 C29 F8 141.1(14) . . ? F6 C29 F8 79.8(10) . . ? C28 C29 F8 103.3(13) . . ? F9 C29 F7 106(3) . . ? F5 C29 F7 45.2(14) . . ? F4 C29 F7 73.6(11) . . ? F6 C29 F7 140.3(11) . . ? C28 C29 F7 106.9(12) . . ? F8 C29 F7 82.8(19) . . ? C23 C30 C28 121.6(7) . . ? C23 C30 H30 119.2 . . ? C28 C30 H30 119.2 . . ? 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 C22 C1 C2 C3 3.2(14) . . . . ? C1 C2 C3 C4 0.1(14) . . . . ? C2 C3 C4 C5 -2.3(14) . . . . ? C3 C4 C5 C6 -175.8(8) . . . . ? C3 C4 C5 C22 1.2(13) . . . . ? C4 C5 C6 C7 176.5(7) . . . . ? C22 C5 C6 C7 -0.5(11) . . . . ? C5 C6 C7 C8 -177.9(7) . . . . ? C5 C6 C7 C20 -1.7(11) . . . . ? C6 C7 C8 C9 177.3(6) . . . . ? C20 C7 C8 C9 1.2(10) . . . . ? C6 C7 C8 C8 -2.2(10) . . . 2_554 ? C20 C7 C8 C8 -178.4(6) . . . 2_554 ? C7 C8 C9 C10 178.1(6) . . . . ? C8 C8 C9 C10 -2.4(10) 2_554 . . . ? C7 C8 C9 C18 -0.5(10) . . . . ? C8 C8 C9 C18 179.0(6) 2_554 . . . ? C8 C9 C10 C11 -177.4(7) . . . . ? C18 C9 C10 C11 1.2(11) . . . . ? C9 C10 C11 C12 175.2(7) . . . . ? C9 C10 C11 C16 -2.3(11) . . . . ? C10 C11 C12 C13 -176.8(8) . . . . ? C16 C11 C12 C13 0.5(13) . . . . ? C11 C12 C13 C14 -2.7(14) . . . . ? C12 C13 C14 C15 1.6(14) . . . . ? C13 C14 C15 C16 1.8(13) . . . . ? C10 C11 C16 C17 -1.3(11) . . . . ? C12 C11 C16 C17 -178.8(7) . . . . ? C10 C11 C16 C15 -179.9(6) . . . . ? C12 C11 C16 C15 2.6(10) . . . . ? C14 C15 C16 C17 177.6(8) . . . . ? C14 C15 C16 C11 -3.8(12) . . . . ? C11 C16 C17 C18 6.0(12) . . . . ? C15 C16 C17 C18 -175.5(7) . . . . ? C16 C17 C18 C19 175.1(7) . . . . ? C16 C17 C18 C9 -6.8(11) . . . . ? C8 C9 C18 C19 -0.1(10) . . . . ? C10 C9 C18 C19 -178.8(6) . . . . ? C8 C9 C18 C17 -178.3(7) . . . . ? C10 C9 C18 C17 3.1(10) . . . . ? C17 C18 C19 C20 178.0(7) . . . . ? C9 C18 C19 C20 0.1(11) . . . . ? C17 C18 C19 C23 -2.2(11) . . . . ? C9 C18 C19 C23 179.8(6) . . . . ? C18 C19 C20 C21 178.0(6) . . . . ? C23 C19 C20 C21 -1.7(11) . . . . ? C18 C19 C20 C7 0.6(10) . . . . ? C23 C19 C20 C7 -179.1(6) . . . . ? C8 C7 C20 C19 -1.2(10) . . . . ? C6 C7 C20 C19 -177.6(6) . . . . ? C8 C7 C20 C21 -178.8(6) . . . . ? C6 C7 C20 C21 4.8(9) . . . . ? C19 C20 C21 C22 176.3(7) . . . . ? C7 C20 C21 C22 -6.2(10) . . . . ? C20 C21 C22 C1 -175.5(7) . . . . ? C20 C21 C22 C5 4.1(12) . . . . ? C2 C1 C22 C21 175.5(9) . . . . ? C2 C1 C22 C5 -4.1(12) . . . . ? C6 C5 C22 C21 -0.5(11) . . . . ? C4 C5 C22 C21 -177.7(8) . . . . ? C6 C5 C22 C1 179.1(7) . . . . ? C4 C5 C22 C1 1.9(11) . . . . ? C18 C19 C23 C24 106.0(9) . . . . ? C20 C19 C23 C24 -74.2(10) . . . . ? C18 C19 C23 C30 -74.4(10) . . . . ? C20 C19 C23 C30 105.3(9) . . . . ? C30 C23 C24 C25 -0.3(12) . . . . ? C19 C23 C24 C25 179.2(7) . . . . ? C23 C24 C25 C27 1.9(12) . . . . ? C23 C24 C25 C26 -177.3(11) . . . . ? C27 C25 C26 F2 84.1(14) . . . . ? C24 C25 C26 F2 -96.8(12) . . . . ? C27 C25 C26 F3 -143.8(12) . . . . ? C24 C25 C26 F3 35(2) . . . . ? C27 C25 C26 F1 -31(2) . . . . ? C24 C25 C26 F1 148.3(12) . . . . ? C27 C25 C26 F11 134.3(15) . . . . ? C24 C25 C26 F11 -47(2) . . . . ? C27 C25 C26 F10 48.7(19) . . . . ? C24 C25 C26 F10 -132.2(13) . . . . ? C24 C25 C27 C28 -1.4(12) . . . . ? C26 C25 C27 C28 177.7(12) . . . . ? C25 C27 C28 C30 -0.6(12) . . . . ? C25 C27 C28 C29 -179.1(12) . . . . ? C27 C28 C29 F9 -94(4) . . . . ? C30 C28 C29 F9 88(4) . . . . ? C27 C28 C29 F5 86.5(17) . . . . ? C30 C28 C29 F5 -92.0(15) . . . . ? C27 C28 C29 F4 -146.7(11) . . . . ? C30 C28 C29 F4 35(2) . . . . ? C27 C28 C29 F6 -36(2) . . . . ? C30 C28 C29 F6 145.2(11) . . . . ? C27 C28 C29 F8 48(2) . . . . ? C30 C28 C29 F8 -130.6(13) . . . . ? C27 C28 C29 F7 134.3(12) . . . . ? C30 C28 C29 F7 -44.2(19) . . . . ? C24 C23 C30 C28 -1.7(12) . . . . ? C19 C23 C30 C28 178.8(7) . . . . ? C27 C28 C30 C23 2.2(12) . . . . ? C29 C28 C30 C23 -179.3(12) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 23.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.256 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 923857'