# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_page_first ? _journal_page_last ? _journal_volume ? _journal_year ? _publ_contact_author 'Prof. Dr. Dietmar Stalke' _publ_contact_author_email dstalke@chemie.uni-goettingen.de _publ_contact_author_name 'Prof. Dr. Dietmar Stalke' loop_ _publ_author_name 'R\"udiger Schmidt' S.Gottling 'Dirk Leusser' 'Dietmar Stalke' F.Wurthner data_antra014 _database_code_depnum_ccdc_archive 'CCDC 294143' _ccdc_journal_depnumber ? _ccdc_compound_id antra014 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H30 O6' _chemical_formula_weight 558.60 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.0294(11) _cell_length_b 7.4771(17) _cell_length_c 19.701(4) _cell_angle_alpha 97.683(4) _cell_angle_beta 92.558(4) _cell_angle_gamma 109.440(4) _cell_volume 689.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3730 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 25.97 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 294 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.05' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Smart Apex with D8 goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11591 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 26.04 _reflns_number_total 2728 _reflns_number_gt 2205 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.6' _computing_cell_refinement 'SAINT-NT V6/6.0' _computing_data_reduction 'SAINT-NT V6/6.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-97 _computing_publication_material SHELXTL-97 _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^)+(0.0714P)^2^+0.2452P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2728 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1326 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 0.8777(3) 0.46906(19) 0.08483(6) 0.0205(3) Uani 1 1 d . . . C21 C 1.1294(4) 0.6363(3) 0.09452(10) 0.0214(4) Uani 1 1 d . . . H21A H 1.265(5) 0.625(3) 0.1282(12) 0.032 Uiso 1 1 d . . . H21B H 1.083(5) 0.753(3) 0.1078(12) 0.032 Uiso 1 1 d . . . H21C H 1.203(5) 0.637(3) 0.0501(12) 0.032 Uiso 1 1 d . . . O2 O 0.4125(3) 0.15368(18) 0.06604(6) 0.0205(3) Uani 1 1 d . . . C22 C 0.2665(4) 0.2068(3) 0.01199(10) 0.0203(4) Uani 1 1 d . . . H22A H 0.257(5) 0.114(3) -0.0298(12) 0.030 Uiso 1 1 d . . . H22B H 0.081(5) 0.201(3) 0.0231(11) 0.030 Uiso 1 1 d . . . H22C H 0.373(5) 0.341(3) 0.0038(11) 0.030 Uiso 1 1 d . . . O3 O 0.0425(3) 0.08613(18) 0.16103(6) 0.0210(3) Uani 1 1 d . . . C23 C -0.1596(4) 0.0506(3) 0.21104(10) 0.0205(4) Uani 1 1 d . . . H23A H -0.323(5) -0.059(3) 0.1871(12) 0.031 Uiso 1 1 d . . . H23B H -0.223(5) 0.165(3) 0.2235(12) 0.031 Uiso 1 1 d . . . H23C H -0.086(5) 0.016(3) 0.2513(12) 0.031 Uiso 1 1 d . . . C1 C 0.8838(4) 0.8714(3) 0.43772(9) 0.0151(4) Uani 1 1 d . . . C2 C 0.7703(4) 0.7431(3) 0.37470(9) 0.0158(4) Uani 1 1 d . . . C3 C 0.6858(4) 0.6383(3) 0.32052(9) 0.0167(4) Uani 1 1 d . . . C4 C 0.6034(4) 0.5177(3) 0.25455(9) 0.0162(4) Uani 1 1 d . . . C5 C 0.7870(4) 0.5576(3) 0.20261(9) 0.0171(4) Uani 1 1 d . . . H5 H 0.961(4) 0.666(3) 0.2110(10) 0.021 Uiso 1 1 d . . . C6 C 0.7165(4) 0.4404(3) 0.13895(9) 0.0170(4) Uani 1 1 d . . . H6 H 0.224(4) 0.336(3) 0.2785(11) 0.020 Uiso 1 1 d . . . C7 C 0.4673(4) 0.2798(3) 0.12665(9) 0.0170(4) Uani 1 1 d . . . C8 C 0.2821(4) 0.2438(3) 0.17836(9) 0.0174(4) Uani 1 1 d . . . C9 C 0.3487(4) 0.3616(3) 0.24221(9) 0.0176(4) Uani 1 1 d . . . C10 C 0.7288(4) 0.8546(2) 0.49626(9) 0.0144(4) Uani 1 1 d . . . C11 C 0.4571(4) 0.7113(3) 0.49449(9) 0.0176(4) Uani 1 1 d . . . H11 H 0.380(4) 0.623(3) 0.4524(11) 0.021 Uiso 1 1 d . . . C12 C 0.3115(4) 0.6956(3) 0.55147(10) 0.0189(4) Uani 1 1 d . . . H12 H 0.126(5) 0.598(3) 0.5506(11) 0.023 Uiso 1 1 d . . . C13 C 0.4277(4) 0.8233(3) 0.61344(9) 0.0197(4) Uani 1 1 d . . . H13 H 0.328(5) 0.812(3) 0.6534(11) 0.024 Uiso 1 1 d . . . C14 C 0.6846(4) 0.9639(3) 0.61717(9) 0.0169(4) Uani 1 1 d . . . H14 H 0.763(4) 1.052(3) 0.6593(11) 0.020 Uiso 1 1 d . . . C15 C 0.8465(4) 0.9839(3) 0.55903(9) 0.0149(4) 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 O1 0.0186(7) 0.0239(7) 0.0144(6) -0.0024(5) 0.0048(5) 0.0027(5) C21 0.0188(10) 0.0229(10) 0.0189(10) 0.0003(8) 0.0053(8) 0.0034(8) O2 0.0241(7) 0.0199(7) 0.0153(6) -0.0055(5) -0.0013(5) 0.0080(6) C22 0.0181(10) 0.0222(10) 0.0144(9) -0.0009(8) 0.0004(7) 0.0004(8) O3 0.0167(7) 0.0196(7) 0.0187(7) -0.0045(5) 0.0020(5) -0.0016(5) C23 0.0166(9) 0.0211(10) 0.0205(10) 0.0031(8) 0.0017(8) 0.0021(8) C1 0.0152(9) 0.0166(9) 0.0126(8) -0.0004(7) -0.0012(7) 0.0059(7) C2 0.0117(8) 0.0186(9) 0.0153(9) 0.0021(7) 0.0030(7) 0.0028(7) C3 0.0135(8) 0.0175(9) 0.0169(9) 0.0031(7) 0.0027(7) 0.0022(7) C4 0.0169(9) 0.0176(9) 0.0135(9) -0.0003(7) -0.0005(7) 0.0064(7) C5 0.0149(9) 0.0182(9) 0.0159(9) 0.0002(7) -0.0007(7) 0.0037(8) C6 0.0169(9) 0.0204(9) 0.0158(9) 0.0018(7) 0.0025(7) 0.0092(8) C7 0.0202(9) 0.0169(9) 0.0124(9) -0.0041(7) -0.0022(7) 0.0072(8) C8 0.0159(9) 0.0156(9) 0.0187(9) 0.0010(7) -0.0014(7) 0.0040(7) C9 0.0170(9) 0.0210(10) 0.0144(9) 0.0016(7) 0.0029(7) 0.0063(8) C10 0.0135(8) 0.0157(9) 0.0143(9) 0.0005(7) 0.0010(7) 0.0062(7) C11 0.0162(9) 0.0177(9) 0.0165(9) -0.0008(7) -0.0010(7) 0.0042(7) C12 0.0136(9) 0.0193(9) 0.0217(10) 0.0043(8) 0.0021(7) 0.0024(8) C13 0.0183(10) 0.0259(10) 0.0153(9) 0.0046(8) 0.0067(7) 0.0067(8) C14 0.0169(9) 0.0202(9) 0.0130(9) 0.0004(7) 0.0010(7) 0.0064(8) C15 0.0152(9) 0.0170(9) 0.0129(9) 0.0012(7) 0.0017(7) 0.0062(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.365(2) . ? O1 C21 1.436(2) . ? C21 H21A 0.96(2) . ? C21 H21B 0.98(2) . ? C21 H21C 0.97(2) . ? O2 C7 1.374(2) . ? O2 C22 1.439(2) . ? C22 H22A 0.99(2) . ? C22 H22B 0.96(2) . ? C22 H22C 1.00(2) . ? O3 C8 1.367(2) . ? O3 C23 1.433(2) . ? C23 H23A 0.99(2) . ? C23 H23B 1.01(2) . ? C23 H23C 0.96(2) . ? C1 C10 1.417(2) . ? C1 C15 1.418(3) 2_776 ? C1 C2 1.428(2) . ? C2 C3 1.204(3) . ? C3 C4 1.437(2) . ? C4 C9 1.402(3) . ? C4 C5 1.404(2) . ? C5 C6 1.388(3) . ? C5 H5 0.96(2) . ? C6 C7 1.402(3) . ? C7 C8 1.403(3) . ? C8 C9 1.393(3) . ? C9 H6 0.97(2) . ? C10 C11 1.424(2) . ? C10 C15 1.431(2) . ? C11 C12 1.364(3) . ? C11 H11 0.96(2) . ? C12 C13 1.413(3) . ? C12 H12 0.97(2) . ? C13 C14 1.359(3) . ? C13 H13 0.95(2) . ? C14 C15 1.430(2) . ? C14 H14 0.97(2) . ? C15 C1 1.418(3) 2_776 ? 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 C6 O1 C21 116.98(14) . . ? O1 C21 H21A 110.4(14) . . ? O1 C21 H21B 110.5(13) . . ? H21A C21 H21B 111.3(19) . . ? O1 C21 H21C 104.4(14) . . ? H21A C21 H21C 109.5(19) . . ? H21B C21 H21C 110.6(19) . . ? C7 O2 C22 113.30(14) . . ? O2 C22 H22A 105.7(13) . . ? O2 C22 H22B 111.0(13) . . ? H22A C22 H22B 110.9(18) . . ? O2 C22 H22C 111.2(13) . . ? H22A C22 H22C 109.7(18) . . ? H22B C22 H22C 108.3(19) . . ? C8 O3 C23 116.59(14) . . ? O3 C23 H23A 104.0(13) . . ? O3 C23 H23B 111.1(13) . . ? H23A C23 H23B 108.9(18) . . ? O3 C23 H23C 111.4(13) . . ? H23A C23 H23C 110.2(19) . . ? H23B C23 H23C 111.0(19) . . ? C10 C1 C15 120.35(16) . 2_776 ? C10 C1 C2 120.46(16) . . ? C15 C1 C2 119.19(16) 2_776 . ? C3 C2 C1 177.19(18) . . ? C2 C3 C4 176.23(19) . . ? C9 C4 C5 120.37(16) . . ? C9 C4 C3 121.19(16) . . ? C5 C4 C3 118.43(16) . . ? C6 C5 C4 119.69(17) . . ? C6 C5 H5 120.0(12) . . ? C4 C5 H5 120.3(12) . . ? O1 C6 C5 124.16(16) . . ? O1 C6 C7 115.27(15) . . ? C5 C6 C7 120.57(16) . . ? O2 C7 C6 120.29(16) . . ? O2 C7 C8 120.37(16) . . ? C6 C7 C8 119.25(16) . . ? O3 C8 C9 124.38(16) . . ? O3 C8 C7 114.91(15) . . ? C9 C8 C7 120.71(16) . . ? C8 C9 C4 119.35(17) . . ? C8 C9 H6 121.2(12) . . ? C4 C9 H6 119.5(12) . . ? C1 C10 C11 121.63(16) . . ? C1 C10 C15 119.65(16) . . ? C11 C10 C15 118.72(16) . . ? C12 C11 C10 120.99(17) . . ? C12 C11 H11 120.4(13) . . ? C10 C11 H11 118.6(12) . . ? C11 C12 C13 120.28(17) . . ? C11 C12 H12 121.5(12) . . ? C13 C12 H12 118.2(12) . . ? C14 C13 C12 120.69(17) . . ? C14 C13 H13 118.8(13) . . ? C12 C13 H13 120.5(13) . . ? C13 C14 C15 120.92(17) . . ? C13 C14 H14 120.8(13) . . ? C15 C14 H14 118.3(13) . . ? C1 C15 C14 121.62(16) 2_776 . ? C1 C15 C10 120.00(16) 2_776 . ? C14 C15 C10 118.37(16) . . ? 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 C10 C1 C2 C3 -171(4) . . . . ? C15 C1 C2 C3 9(4) 2_776 . . . ? C1 C2 C3 C4 6(7) . . . . ? C2 C3 C4 C9 163(3) . . . . ? C2 C3 C4 C5 -16(3) . . . . ? C9 C4 C5 C6 -0.6(3) . . . . ? C3 C4 C5 C6 178.26(17) . . . . ? C21 O1 C6 C5 -2.6(3) . . . . ? C21 O1 C6 C7 177.70(16) . . . . ? C4 C5 C6 O1 178.71(16) . . . . ? C4 C5 C6 C7 -1.6(3) . . . . ? C22 O2 C7 C6 -88.1(2) . . . . ? C22 O2 C7 C8 95.4(2) . . . . ? O1 C6 C7 O2 6.2(2) . . . . ? C5 C6 C7 O2 -173.51(16) . . . . ? O1 C6 C7 C8 -177.22(15) . . . . ? C5 C6 C7 C8 3.1(3) . . . . ? C23 O3 C8 C9 4.6(3) . . . . ? C23 O3 C8 C7 -176.60(15) . . . . ? O2 C7 C8 O3 -4.6(2) . . . . ? C6 C7 C8 O3 178.81(15) . . . . ? O2 C7 C8 C9 174.25(16) . . . . ? C6 C7 C8 C9 -2.3(3) . . . . ? O3 C8 C9 C4 178.88(16) . . . . ? C7 C8 C9 C4 0.1(3) . . . . ? C5 C4 C9 C8 1.4(3) . . . . ? C3 C4 C9 C8 -177.49(17) . . . . ? C15 C1 C10 C11 179.74(16) 2_776 . . . ? C2 C1 C10 C11 -0.1(3) . . . . ? C15 C1 C10 C15 -0.4(3) 2_776 . . . ? C2 C1 C10 C15 179.74(16) . . . . ? C1 C10 C11 C12 179.27(17) . . . . ? C15 C10 C11 C12 -0.5(3) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C12 C13 C14 C15 -1.3(3) . . . . ? C13 C14 C15 C1 -179.36(17) . . . 2_776 ? C13 C14 C15 C10 1.3(3) . . . . ? C1 C10 C15 C1 0.4(3) . . . 2_776 ? C11 C10 C15 C1 -179.74(16) . . . 2_776 ? C1 C10 C15 C14 179.79(16) . . . . ? C11 C10 C15 C14 -0.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.278 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.056 # Attachment '5_corrected.cif' data_rs007 _database_code_depnum_ccdc_archive 'CCDC 294144' _ccdc_compound_id rs007 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H34 Cl6 O6' _chemical_formula_weight 847.39 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 35.241(3) _cell_length_b 5.6021(5) _cell_length_c 20.1942(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.868(2) _cell_angle_gamma 90.00 _cell_volume 3986.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9159 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.02 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.05' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Smart Apex with D8 goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46446 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.04 _reflns_number_total 7040 _reflns_number_gt 6465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V5.6' _computing_cell_refinement 'SAINT-NT V6/6.0' _computing_data_reduction 'SAINT-NT V6/6.0' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-97 _computing_publication_material SHELXTL-97 _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^)+(0.0281P)^2^+8.0463P] 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 7040 _refine_ls_number_parameters 493 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.236 _refine_ls_restrained_S_all 1.236 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.45286(6) 1.3713(4) 0.49115(9) 0.0188(4) Uani 1 1 d . . . O2 O 0.45122(5) 1.0744(4) 0.38770(9) 0.0168(4) Uani 1 1 d . . . O3 O 0.39690(6) 0.7481(4) 0.37269(10) 0.0208(5) Uani 1 1 d . . . O4 O 0.06360(6) 0.2960(4) 0.90847(10) 0.0220(5) Uani 1 1 d . . . O5 O 0.05478(6) 0.5854(4) 1.01213(10) 0.0194(5) Uani 1 1 d . . . O6 O 0.10390(6) 0.9285(4) 1.04115(10) 0.0220(5) Uani 1 1 d . . . C1 C 0.29204(8) 0.8920(5) 0.67514(13) 0.0156(6) Uani 1 1 d . . . C2 C 0.29059(8) 1.0310(5) 0.73301(14) 0.0157(6) Uani 1 1 d . . . C3 C 0.31525(8) 1.2282(5) 0.74381(14) 0.0177(6) Uani 1 1 d . . . H3 H 0.3335 1.2662 0.7113 0.021 Uiso 1 1 calc R . . C4 C 0.31337(9) 1.3638(6) 0.79950(15) 0.0214(7) Uani 1 1 d . . . H4 H 0.3302 1.4946 0.8057 0.026 Uiso 1 1 calc R . . C5 C 0.28599(9) 1.3088(6) 0.84859(15) 0.0227(7) Uani 1 1 d . . . H5 H 0.2849 1.4021 0.8878 0.027 Uiso 1 1 calc R . . C6 C 0.26167(9) 1.1253(6) 0.83965(14) 0.0209(7) Uani 1 1 d . . . H6 H 0.2434 1.0934 0.8725 0.025 Uiso 1 1 calc R . . C7 C 0.26272(8) 0.9781(5) 0.78220(14) 0.0175(6) Uani 1 1 d . . . C8 C 0.23736(8) 0.7871(5) 0.77181(14) 0.0166(6) Uani 1 1 d . . . C9 C 0.23970(8) 0.6404(5) 0.71451(13) 0.0159(6) Uani 1 1 d . . . C10 C 0.21571(8) 0.4433(5) 0.70481(14) 0.0177(6) Uani 1 1 d . . . H10 H 0.1979 0.4044 0.7379 0.021 Uiso 1 1 calc R . . C11 C 0.21733(8) 0.3042(6) 0.64845(14) 0.0193(6) Uani 1 1 d . . . C12 C 0.19366(9) 0.0996(6) 0.63850(16) 0.0233(7) Uani 1 1 d . . . H12 H 0.1769 0.0522 0.6725 0.028 Uiso 1 1 calc R . . C13 C 0.19470(9) -0.0277(6) 0.58160(17) 0.0278(8) Uani 1 1 d . . . H13 H 0.1784 -0.1615 0.5758 0.033 Uiso 1 1 calc R . . C14 C 0.21984(9) 0.0372(6) 0.53074(17) 0.0279(8) Uani 1 1 d . . . H14 H 0.2200 -0.0514 0.4906 0.034 Uiso 1 1 calc R . . C15 C 0.24377(9) 0.2246(6) 0.53874(15) 0.0232(7) Uani 1 1 d . . . H15 H 0.2608 0.2633 0.5044 0.028 Uiso 1 1 calc R . . C16 C 0.24385(8) 0.3645(6) 0.59742(14) 0.0197(6) Uani 1 1 d . . . C17 C 0.26805(8) 0.5553(5) 0.60782(14) 0.0173(6) Uani 1 1 d . . . H17 H 0.2860 0.5930 0.5747 0.021 Uiso 1 1 calc R . . C18 C 0.26720(8) 0.6949(5) 0.66513(13) 0.0161(6) Uani 1 1 d . . . C19 C 0.31884(8) 0.9480(5) 0.62496(14) 0.0166(6) Uani 1 1 d . . . C20 C 0.34093(8) 0.9859(5) 0.58173(14) 0.0173(6) Uani 1 1 d . . . C21 C 0.36824(8) 1.0175(5) 0.53065(14) 0.0161(6) Uani 1 1 d . . . C22 C 0.39616(8) 1.1920(5) 0.53688(14) 0.0171(6) Uani 1 1 d . . . H22 H 0.3962 1.2979 0.5736 0.021 Uiso 1 1 calc R . . C23 C 0.42392(8) 1.2110(5) 0.48944(14) 0.0164(6) Uani 1 1 d . . . C24 C 0.42375(8) 1.0556(5) 0.43511(14) 0.0157(6) Uani 1 1 d . . . C25 C 0.39495(8) 0.8858(5) 0.42836(14) 0.0174(6) Uani 1 1 d . . . C26 C 0.36724(8) 0.8652(5) 0.47584(14) 0.0173(6) Uani 1 1 d . . . H26 H 0.3478 0.7488 0.4712 0.021 Uiso 1 1 calc R . . C27 C 0.20754(8) 0.7438(6) 0.81769(14) 0.0189(6) Uani 1 1 d . . . C28 C 0.18099(9) 0.7073(6) 0.85262(14) 0.0210(7) Uani 1 1 d . . . C29 C 0.14866(8) 0.6734(6) 0.89401(14) 0.0181(6) Uani 1 1 d . . . C30 C 0.14357(8) 0.8246(6) 0.94767(14) 0.0182(6) Uani 1 1 d . . . H30 H 0.1615 0.9471 0.9573 0.022 Uiso 1 1 calc R . . C31 C 0.11188(8) 0.7939(5) 0.98708(14) 0.0167(6) Uani 1 1 d . . . C32 C 0.08546(8) 0.6164(5) 0.97204(13) 0.0163(6) Uani 1 1 d . . . C33 C 0.09096(8) 0.4658(6) 0.91804(14) 0.0184(6) Uani 1 1 d . . . C34 C 0.12292(8) 0.4924(6) 0.87917(14) 0.0193(6) Uani 1 1 d . . . H34 H 0.1271 0.3881 0.8429 0.023 Uiso 1 1 calc R . . C35 C 0.45474(9) 1.5278(6) 0.54711(14) 0.0197(6) Uani 1 1 d . . . H35A H 0.4324 1.6318 0.5469 0.030 Uiso 1 1 calc R . . H35B H 0.4778 1.6255 0.5448 0.030 Uiso 1 1 calc R . . H35C H 0.4554 1.4332 0.5879 0.030 Uiso 1 1 calc R . . C36 C 0.48151(8) 0.9059(6) 0.39779(14) 0.0207(7) Uani 1 1 d . . . H36A H 0.4935 0.9334 0.4412 0.031 Uiso 1 1 calc R . . H36B H 0.5004 0.9260 0.3631 0.031 Uiso 1 1 calc R . . H36C H 0.4713 0.7433 0.3960 0.031 Uiso 1 1 calc R . . C37 C 0.36997(9) 0.5599(6) 0.36508(15) 0.0208(7) Uani 1 1 d . . . H37A H 0.3717 0.4529 0.4034 0.031 Uiso 1 1 calc R . . H37B H 0.3753 0.4702 0.3246 0.031 Uiso 1 1 calc R . . H37C H 0.3443 0.6274 0.3620 0.031 Uiso 1 1 calc R . . C38 C 0.06716(9) 0.1429(6) 0.85243(15) 0.0245(7) Uani 1 1 d . . . H38A H 0.0665 0.2387 0.8118 0.037 Uiso 1 1 calc R . . H38B H 0.0461 0.0286 0.8514 0.037 Uiso 1 1 calc R . . H38C H 0.0913 0.0563 0.8555 0.037 Uiso 1 1 calc R . . C39 C 0.02464(9) 0.7512(6) 0.99635(17) 0.0279(7) Uani 1 1 d . . . H39A H 0.0345 0.9147 0.9984 0.042 Uiso 1 1 calc R . . H39B H 0.0042 0.7328 1.0283 0.042 Uiso 1 1 calc R . . H39C H 0.0148 0.7187 0.9516 0.042 Uiso 1 1 calc R . . C40 C 0.12946(9) 1.1192(5) 1.05688(15) 0.0216(7) Uani 1 1 d . . . H40A H 0.1547 1.0538 1.0666 0.032 Uiso 1 1 calc R . . H40B H 0.1203 1.2056 1.0957 0.032 Uiso 1 1 calc R . . H40C H 0.1309 1.2287 1.0192 0.032 Uiso 1 1 calc R . . C50 C 0.93914(10) 0.2283(6) 0.83368(16) 0.0280(8) Uani 1 1 d . . . H50 H 0.9366 0.2859 0.8803 0.034 Uiso 1 1 calc R . . Cl1 Cl 0.89601(3) 0.2749(2) 0.79129(5) 0.0483(3) Uani 1 1 d . . . Cl2 Cl 0.97624(3) 0.38649(16) 0.79565(5) 0.0375(2) Uani 1 1 d . . . Cl3 Cl 0.95093(3) -0.07680(15) 0.83501(5) 0.0370(2) Uani 1 1 d . . . C52 C 0.42767(8) 0.5296(5) 0.73815(14) 0.0171(6) Uani 1 1 d . . . H52 H 0.4231 0.5557 0.7864 0.020 Uiso 1 1 calc R . . Cl4 Cl 0.39083(2) 0.66962(13) 0.69200(4) 0.02091(17) Uani 1 1 d . . . Cl5 Cl 0.47193(2) 0.65420(13) 0.71804(4) 0.02269(17) Uani 1 1 d . . . Cl6 Cl 0.42760(2) 0.22070(13) 0.72227(4) 0.02287(18) 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 O1 0.0195(11) 0.0229(11) 0.0141(10) -0.0019(9) 0.0045(8) -0.0063(9) O2 0.0165(10) 0.0218(11) 0.0121(10) 0.0026(8) 0.0054(8) 0.0000(9) O3 0.0244(12) 0.0223(11) 0.0157(10) -0.0045(9) 0.0045(8) -0.0074(9) O4 0.0221(11) 0.0256(12) 0.0185(11) -0.0050(9) 0.0050(9) -0.0038(9) O5 0.0177(11) 0.0230(11) 0.0179(10) 0.0000(9) 0.0081(8) -0.0017(9) O6 0.0209(11) 0.0266(12) 0.0186(11) -0.0075(9) 0.0056(8) -0.0078(9) C1 0.0128(14) 0.0207(15) 0.0133(14) 0.0037(12) 0.0001(11) 0.0038(12) C2 0.0139(14) 0.0186(15) 0.0145(14) 0.0043(12) 0.0009(11) 0.0038(12) C3 0.0160(15) 0.0205(16) 0.0167(14) 0.0052(12) 0.0029(11) 0.0010(12) C4 0.0217(16) 0.0181(16) 0.0244(16) 0.0007(13) -0.0008(13) -0.0008(13) C5 0.0277(17) 0.0248(17) 0.0158(15) -0.0046(13) 0.0018(12) 0.0047(14) C6 0.0218(16) 0.0268(17) 0.0142(14) 0.0029(13) 0.0047(12) 0.0049(14) C7 0.0172(15) 0.0208(16) 0.0144(14) 0.0032(12) 0.0018(11) 0.0067(12) C8 0.0153(15) 0.0204(16) 0.0141(14) 0.0053(12) 0.0041(11) 0.0038(12) C9 0.0133(14) 0.0219(16) 0.0125(14) 0.0043(12) 0.0000(11) 0.0035(12) C10 0.0148(15) 0.0210(16) 0.0173(15) 0.0047(12) 0.0004(11) 0.0001(12) C11 0.0188(15) 0.0208(16) 0.0183(15) 0.0039(13) -0.0024(12) 0.0046(13) C12 0.0188(16) 0.0207(16) 0.0302(17) 0.0087(14) -0.0033(13) 0.0001(13) C13 0.0269(18) 0.0181(16) 0.0382(19) 0.0023(15) -0.0115(15) 0.0001(14) C14 0.0316(19) 0.0241(17) 0.0279(17) -0.0047(14) -0.0099(14) 0.0026(15) C15 0.0247(17) 0.0262(17) 0.0187(15) -0.0009(13) -0.0006(13) 0.0022(14) C16 0.0205(16) 0.0213(16) 0.0171(15) 0.0036(12) -0.0035(12) 0.0044(13) C17 0.0147(14) 0.0244(16) 0.0130(14) 0.0043(12) 0.0031(11) 0.0044(13) C18 0.0134(14) 0.0211(16) 0.0137(14) 0.0037(12) -0.0007(11) 0.0045(12) C19 0.0109(14) 0.0206(16) 0.0184(15) -0.0004(12) -0.0011(12) 0.0017(12) C20 0.0147(15) 0.0203(15) 0.0170(14) 0.0000(12) 0.0005(12) -0.0004(12) C21 0.0132(14) 0.0203(15) 0.0147(14) 0.0047(12) 0.0024(11) 0.0002(12) C22 0.0196(15) 0.0201(15) 0.0117(13) -0.0001(12) 0.0014(11) 0.0023(13) C23 0.0159(15) 0.0181(15) 0.0151(14) 0.0042(12) -0.0008(11) 0.0003(12) C24 0.0139(14) 0.0195(15) 0.0140(14) 0.0054(12) 0.0035(11) 0.0020(12) C25 0.0192(15) 0.0208(16) 0.0122(14) 0.0018(12) 0.0014(11) 0.0003(12) C26 0.0152(14) 0.0213(16) 0.0153(14) 0.0038(12) 0.0016(11) -0.0043(12) C27 0.0191(16) 0.0222(16) 0.0156(14) 0.0026(12) 0.0018(12) -0.0001(13) C28 0.0213(16) 0.0245(17) 0.0171(15) 0.0011(13) 0.0015(13) -0.0005(13) C29 0.0139(14) 0.0250(16) 0.0154(14) 0.0058(12) 0.0043(11) 0.0037(13) C30 0.0154(15) 0.0245(16) 0.0146(14) 0.0046(12) 0.0006(11) -0.0017(13) C31 0.0167(15) 0.0205(15) 0.0129(14) 0.0019(12) 0.0029(11) 0.0024(12) C32 0.0142(14) 0.0229(16) 0.0119(14) 0.0019(12) 0.0039(11) 0.0009(12) C33 0.0178(15) 0.0225(16) 0.0148(14) 0.0054(12) 0.0006(11) -0.0011(13) C34 0.0179(15) 0.0274(17) 0.0127(14) -0.0009(13) 0.0033(11) 0.0031(13) C35 0.0188(15) 0.0231(16) 0.0174(15) -0.0048(13) 0.0039(12) -0.0032(13) C36 0.0181(15) 0.0279(17) 0.0162(15) 0.0017(13) 0.0033(12) -0.0009(13) C37 0.0221(16) 0.0215(16) 0.0188(15) -0.0025(13) 0.0023(12) -0.0046(13) C38 0.0302(18) 0.0267(17) 0.0168(15) -0.0054(13) 0.0002(13) -0.0035(14) C39 0.0173(16) 0.0283(18) 0.0383(19) 0.0029(15) 0.0085(14) 0.0008(14) C40 0.0223(16) 0.0194(16) 0.0231(16) -0.0029(13) 0.0019(12) -0.0037(13) C50 0.0352(19) 0.0276(18) 0.0216(16) 0.0012(14) 0.0089(14) 0.0052(15) Cl1 0.0381(5) 0.0663(7) 0.0403(5) 0.0025(5) -0.0025(4) 0.0123(5) Cl2 0.0404(5) 0.0288(5) 0.0439(5) 0.0093(4) 0.0157(4) 0.0055(4) Cl3 0.0458(5) 0.0239(4) 0.0416(5) -0.0005(4) 0.0175(4) 0.0043(4) C52 0.0237(16) 0.0134(14) 0.0142(14) 0.0006(12) 0.0018(12) -0.0007(12) Cl4 0.0197(4) 0.0188(4) 0.0241(4) 0.0011(3) -0.0027(3) 0.0024(3) Cl5 0.0201(4) 0.0203(4) 0.0276(4) 0.0007(3) -0.0027(3) -0.0039(3) Cl6 0.0296(4) 0.0125(3) 0.0267(4) 0.0023(3) 0.0049(3) -0.0004(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 C23 1.359(4) . ? O1 C35 1.431(3) . ? O2 C24 1.376(3) . ? O2 C36 1.437(4) . ? O3 C25 1.366(3) . ? O3 C37 1.425(4) . ? O4 C33 1.366(4) . ? O4 C38 1.427(4) . ? O5 C32 1.371(3) . ? O5 C39 1.443(4) . ? O6 C31 1.360(3) . ? O6 C40 1.430(4) . ? C1 C2 1.406(4) . ? C1 C18 1.421(4) . ? C1 C19 1.431(4) . ? C2 C3 1.420(4) . ? C2 C7 1.438(4) . ? C3 C4 1.360(4) . ? C3 H3 0.9500 . ? C4 C5 1.427(4) . ? C4 H4 0.9500 . ? C5 C6 1.349(5) . ? C5 H5 0.9500 . ? C6 C7 1.424(4) . ? C6 H6 0.9500 . ? C7 C8 1.408(4) . ? C8 C9 1.423(4) . ? C8 C27 1.432(4) . ? C9 C10 1.403(4) . ? C9 C18 1.434(4) . ? C10 C11 1.381(4) . ? C10 H10 0.9500 . ? C11 C12 1.430(4) . ? C11 C16 1.442(4) . ? C12 C13 1.353(5) . ? C12 H12 0.9500 . ? C13 C14 1.414(5) . ? C13 H13 0.9500 . ? C14 C15 1.355(5) . ? C14 H14 0.9500 . ? C15 C16 1.421(4) . ? C15 H15 0.9500 . ? C16 C17 1.381(4) . ? C17 C18 1.398(4) . ? C17 H17 0.9500 . ? C19 C20 1.197(4) . ? C20 C21 1.432(4) . ? C21 C22 1.391(4) . ? C21 C26 1.398(4) . ? C22 C23 1.384(4) . ? C22 H22 0.9500 . ? C23 C24 1.401(4) . ? C24 C25 1.396(4) . ? C25 C26 1.384(4) . ? C26 H26 0.9500 . ? C27 C28 1.198(4) . ? C28 C29 1.436(4) . ? C29 C30 1.389(4) . ? C29 C34 1.390(4) . ? C30 C31 1.392(4) . ? C30 H30 0.9500 . ? C31 C32 1.393(4) . ? C32 C33 1.395(4) . ? C33 C34 1.391(4) . ? C34 H34 0.9500 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C50 Cl1 1.753(4) . ? C50 Cl3 1.759(3) . ? C50 Cl2 1.765(3) . ? C50 H50 1.0000 . ? C52 Cl6 1.760(3) . ? C52 Cl5 1.762(3) . ? C52 Cl4 1.770(3) . ? C52 H52 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 C23 O1 C35 116.8(2) . . ? C24 O2 C36 112.3(2) . . ? C25 O3 C37 117.7(2) . . ? C33 O4 C38 117.4(2) . . ? C32 O5 C39 111.9(2) . . ? C31 O6 C40 117.1(2) . . ? C2 C1 C18 121.2(3) . . ? C2 C1 C19 120.0(3) . . ? C18 C1 C19 118.8(3) . . ? C1 C2 C3 121.9(3) . . ? C1 C2 C7 119.6(3) . . ? C3 C2 C7 118.5(3) . . ? C4 C3 C2 121.6(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 121.7(3) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C8 C7 C6 122.5(3) . . ? C8 C7 C2 119.5(3) . . ? C6 C7 C2 118.0(3) . . ? C7 C8 C9 121.1(3) . . ? C7 C8 C27 120.2(3) . . ? C9 C8 C27 118.7(3) . . ? C10 C9 C8 121.7(3) . . ? C10 C9 C18 118.9(3) . . ? C8 C9 C18 119.4(3) . . ? C11 C10 C9 121.8(3) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 C12 122.5(3) . . ? C10 C11 C16 119.5(3) . . ? C12 C11 C16 118.1(3) . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 121.4(3) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 123.2(3) . . ? C17 C16 C11 118.6(3) . . ? C15 C16 C11 118.3(3) . . ? C16 C17 C18 122.5(3) . . ? C16 C17 H17 118.7 . . ? C18 C17 H17 118.7 . . ? C17 C18 C1 122.1(3) . . ? C17 C18 C9 118.7(3) . . ? C1 C18 C9 119.2(3) . . ? C20 C19 C1 177.2(3) . . ? C19 C20 C21 176.7(3) . . ? C22 C21 C26 120.7(3) . . ? C22 C21 C20 120.2(3) . . ? C26 C21 C20 119.0(3) . . ? C23 C22 C21 119.8(3) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? O1 C23 C22 124.8(3) . . ? O1 C23 C24 115.1(2) . . ? C22 C23 C24 120.0(3) . . ? O2 C24 C25 120.2(3) . . ? O2 C24 C23 120.2(3) . . ? C25 C24 C23 119.6(3) . . ? O3 C25 C26 124.6(3) . . ? O3 C25 C24 114.8(2) . . ? C26 C25 C24 120.6(3) . . ? C25 C26 C21 119.2(3) . . ? C25 C26 H26 120.4 . . ? C21 C26 H26 120.4 . . ? C28 C27 C8 175.7(3) . . ? C27 C28 C29 177.7(3) . . ? C30 C29 C34 121.4(3) . . ? C30 C29 C28 119.1(3) . . ? C34 C29 C28 119.5(3) . . ? C29 C30 C31 119.0(3) . . ? C29 C30 H30 120.5 . . ? C31 C30 H30 120.5 . . ? O6 C31 C30 124.6(3) . . ? O6 C31 C32 115.2(2) . . ? C30 C31 C32 120.2(3) . . ? O5 C32 C31 119.5(3) . . ? O5 C32 C33 120.3(3) . . ? C31 C32 C33 120.1(3) . . ? O4 C33 C34 124.8(3) . . ? O4 C33 C32 115.2(2) . . ? C34 C33 C32 120.0(3) . . ? C29 C34 C33 119.2(3) . . ? C29 C34 H34 120.4 . . ? C33 C34 H34 120.4 . . ? O1 C35 H35A 109.5 . . ? O1 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O1 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O2 C36 H36A 109.5 . . ? O2 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O2 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O3 C37 H37A 109.5 . . ? O3 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O3 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O4 C38 H38A 109.5 . . ? O4 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O4 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O5 C39 H39A 109.5 . . ? O5 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O5 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? O6 C40 H40A 109.5 . . ? O6 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O6 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? Cl1 C50 Cl3 110.8(2) . . ? Cl1 C50 Cl2 110.81(18) . . ? Cl3 C50 Cl2 108.56(18) . . ? Cl1 C50 H50 108.9 . . ? Cl3 C50 H50 108.9 . . ? Cl2 C50 H50 108.9 . . ? Cl6 C52 Cl5 110.27(16) . . ? Cl6 C52 Cl4 109.94(16) . . ? Cl5 C52 Cl4 110.35(15) . . ? Cl6 C52 H52 108.7 . . ? Cl5 C52 H52 108.7 . . ? Cl4 C52 H52 108.7 . . ? 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 C18 C1 C2 C3 179.9(3) . . . . ? C19 C1 C2 C3 -0.2(4) . . . . ? C18 C1 C2 C7 -2.0(4) . . . . ? C19 C1 C2 C7 178.0(3) . . . . ? C1 C2 C3 C4 179.1(3) . . . . ? C7 C2 C3 C4 0.9(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 C6 -0.9(5) . . . . ? C4 C5 C6 C7 1.1(5) . . . . ? C5 C6 C7 C8 -179.5(3) . . . . ? C5 C6 C7 C2 -0.3(4) . . . . ? C1 C2 C7 C8 0.2(4) . . . . ? C3 C2 C7 C8 178.5(3) . . . . ? C1 C2 C7 C6 -178.9(3) . . . . ? C3 C2 C7 C6 -0.7(4) . . . . ? C6 C7 C8 C9 -178.7(3) . . . . ? C2 C7 C8 C9 2.2(4) . . . . ? C6 C7 C8 C27 4.1(4) . . . . ? C2 C7 C8 C27 -175.0(3) . . . . ? C7 C8 C9 C10 177.2(3) . . . . ? C27 C8 C9 C10 -5.5(4) . . . . ? C7 C8 C9 C18 -2.9(4) . . . . ? C27 C8 C9 C18 174.4(3) . . . . ? C8 C9 C10 C11 178.4(3) . . . . ? C18 C9 C10 C11 -1.5(4) . . . . ? C9 C10 C11 C12 178.6(3) . . . . ? C9 C10 C11 C16 -1.1(4) . . . . ? C10 C11 C12 C13 177.2(3) . . . . ? C16 C11 C12 C13 -3.1(4) . . . . ? C11 C12 C13 C14 1.0(5) . . . . ? C12 C13 C14 C15 1.3(5) . . . . ? C13 C14 C15 C16 -1.4(5) . . . . ? C14 C15 C16 C17 179.3(3) . . . . ? C14 C15 C16 C11 -0.8(4) . . . . ? C10 C11 C16 C17 2.6(4) . . . . ? C12 C11 C16 C17 -177.1(3) . . . . ? C10 C11 C16 C15 -177.3(3) . . . . ? C12 C11 C16 C15 3.0(4) . . . . ? C15 C16 C17 C18 178.4(3) . . . . ? C11 C16 C17 C18 -1.5(4) . . . . ? C16 C17 C18 C1 -179.5(3) . . . . ? C16 C17 C18 C9 -1.1(4) . . . . ? C2 C1 C18 C17 179.7(3) . . . . ? C19 C1 C18 C17 -0.3(4) . . . . ? C2 C1 C18 C9 1.2(4) . . . . ? C19 C1 C18 C9 -178.7(3) . . . . ? C10 C9 C18 C17 2.6(4) . . . . ? C8 C9 C18 C17 -177.3(3) . . . . ? C10 C9 C18 C1 -179.0(3) . . . . ? C8 C9 C18 C1 1.2(4) . . . . ? C2 C1 C19 C20 168(6) . . . . ? C18 C1 C19 C20 -13(7) . . . . ? C1 C19 C20 C21 -48(10) . . . . ? C19 C20 C21 C22 -116(5) . . . . ? C19 C20 C21 C26 61(6) . . . . ? C26 C21 C22 C23 -1.9(4) . . . . ? C20 C21 C22 C23 175.7(3) . . . . ? C35 O1 C23 C22 1.2(4) . . . . ? C35 O1 C23 C24 -177.9(2) . . . . ? C21 C22 C23 O1 -178.7(3) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? C36 O2 C24 C25 -83.7(3) . . . . ? C36 O2 C24 C23 98.1(3) . . . . ? O1 C23 C24 O2 -1.1(4) . . . . ? C22 C23 C24 O2 179.8(3) . . . . ? O1 C23 C24 C25 -179.3(3) . . . . ? C22 C23 C24 C25 1.5(4) . . . . ? C37 O3 C25 C26 -4.3(4) . . . . ? C37 O3 C25 C24 175.6(2) . . . . ? O2 C24 C25 O3 0.0(4) . . . . ? C23 C24 C25 O3 178.2(2) . . . . ? O2 C24 C25 C26 179.9(3) . . . . ? C23 C24 C25 C26 -1.9(4) . . . . ? O3 C25 C26 C21 -179.8(3) . . . . ? C24 C25 C26 C21 0.4(4) . . . . ? C22 C21 C26 C25 1.6(4) . . . . ? C20 C21 C26 C25 -176.1(3) . . . . ? C7 C8 C27 C28 129(4) . . . . ? C9 C8 C27 C28 -48(5) . . . . ? C8 C27 C28 C29 -72(10) . . . . ? C27 C28 C29 C30 -57(8) . . . . ? C27 C28 C29 C34 122(8) . . . . ? C34 C29 C30 C31 -0.3(4) . . . . ? C28 C29 C30 C31 178.9(3) . . . . ? C40 O6 C31 C30 2.0(4) . . . . ? C40 O6 C31 C32 -177.6(3) . . . . ? C29 C30 C31 O6 179.4(3) . . . . ? C29 C30 C31 C32 -1.0(4) . . . . ? C39 O5 C32 C31 82.4(3) . . . . ? C39 O5 C32 C33 -100.0(3) . . . . ? O6 C31 C32 O5 -1.7(4) . . . . ? C30 C31 C32 O5 178.7(3) . . . . ? O6 C31 C32 C33 -179.3(3) . . . . ? C30 C31 C32 C33 1.1(4) . . . . ? C38 O4 C33 C34 -3.4(4) . . . . ? C38 O4 C33 C32 177.8(3) . . . . ? O5 C32 C33 O4 1.5(4) . . . . ? C31 C32 C33 O4 179.1(3) . . . . ? O5 C32 C33 C34 -177.5(3) . . . . ? C31 C32 C33 C34 0.1(4) . . . . ? C30 C29 C34 C33 1.5(4) . . . . ? C28 C29 C34 C33 -177.7(3) . . . . ? O4 C33 C34 C29 179.8(3) . . . . ? C32 C33 C34 C29 -1.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.430 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.067