# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 loop_ _publ_author_name 'Felix Caroline' 'Roselyne Baudry' 'Claude Bavoux' 'Isabelle Dumazet-Bonnamour' 'Roger Lamartine' ; M.Perrin ; 'Francis Vocanson' _publ_contact_author_name 'Dr Caroline Felix' _publ_contact_author_address ; LACE UMR CNRS 5634 Universite Claude Bernard Lyon 1 Bat. J. Raulin 43 Bd du 11 Novembre 1918 Villeurbanne 69622 FRANCE ; _publ_contact_author_email C.FELIX@CDLYON.UNIV-LYON1.FR _publ_section_title ; Biaryl cross-coupling reactions : convenient route to new functionalized calix[8]arene ; data_rb126 _database_code_CSD 201017 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H28 Br4 Cl4 O4' _chemical_formula_weight 949.99 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 27.894(6) _cell_length_b 14.665(3) _cell_length_c 21.659(4) _cell_angle_alpha 90.00 _cell_angle_beta 126.01(3) _cell_angle_gamma 90.00 _cell_volume 7167(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3728 _exptl_absorpt_coefficient_mu 4.827 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12771 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.1324 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.41 _reflns_number_total 7763 _reflns_number_gt 3776 _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^)+(0.0803P)^2^+32.7233P] 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 7763 _refine_ls_number_parameters 461 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1806 _refine_ls_R_factor_gt 0.0740 _refine_ls_wR_factor_ref 0.2033 _refine_ls_wR_factor_gt 0.1470 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.615 _refine_ls_shift/su_mean 0.030 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 Br27 Br 0.10881(4) 0.32201(6) 0.07349(6) 0.0514(3) Uani 1 1 d . . . Br28 Br 0.04465(5) -0.08708(7) -0.13846(5) 0.0557(3) Uani 1 1 d . . . Br25 Br 0.55304(4) 0.04325(7) 0.21328(6) 0.0585(3) Uani 1 1 d . . . Br26 Br 0.37224(6) 0.37035(7) 0.14206(7) 0.0797(4) Uani 1 1 d . . . O28 O 0.0749(3) -0.2149(4) 0.1468(3) 0.0415(15) Uani 1 1 d . . . O27 O 0.2079(2) -0.0528(4) 0.1919(3) 0.0412(14) Uani 1 1 d . . . O25 O 0.3326(3) -0.0690(4) -0.0907(3) 0.0460(15) Uani 1 1 d . . . O26 O 0.2818(3) -0.0154(4) 0.0866(3) 0.0471(15) Uani 1 1 d . . . C27 C 0.1869(4) 0.0346(5) 0.1694(4) 0.0294(18) Uani 1 1 d . . . C1 C 0.0575(4) -0.3503(5) 0.0448(5) 0.040(2) Uani 1 1 d . . . H1A H 0.0896 -0.3619 0.0979 0.048 Uiso 1 1 calc R . . H1B H 0.0206 -0.3627 0.0385 0.048 Uiso 1 1 calc R . . C5 C 0.0666(3) -0.0653(5) 0.0069(5) 0.035(2) Uani 1 1 d . . . H5 H 0.0691 -0.0038 -0.0011 0.042 Uiso 1 1 calc R . . C3 C 0.0521(4) -0.2205(6) -0.0370(5) 0.040(2) Uani 1 1 d . . . H3 H 0.0449 -0.2621 -0.0739 0.048 Uiso 1 1 calc R . . C6 C 0.0730(3) -0.0931(5) 0.0719(4) 0.0331(19) Uani 1 1 d . . . C15 C 0.3279(4) 0.2133(5) 0.1692(5) 0.038(2) Uani 1 1 d . . . H15 H 0.3339 0.2470 0.2096 0.046 Uiso 1 1 calc R . . C8 C 0.1278(4) 0.0512(5) 0.1389(4) 0.0288(18) Uani 1 1 d . . . C10 C 0.1406(4) 0.2049(5) 0.1136(5) 0.037(2) Uani 1 1 d . . . C4 C 0.0563(4) -0.1290(5) -0.0465(4) 0.036(2) Uani 1 1 d . . . C16 C 0.3420(4) 0.2505(6) 0.1228(5) 0.045(2) Uani 1 1 d . . . C20 C 0.3774(4) 0.0117(5) 0.0269(5) 0.037(2) Uani 1 1 d . . . C14 C 0.3048(4) 0.1254(6) 0.1550(5) 0.038(2) Uani 1 1 d . . . C22 C 0.4822(4) 0.0040(5) 0.1192(4) 0.036(2) Uani 1 1 d . . . C9 C 0.1043(4) 0.1359(6) 0.1110(4) 0.037(2) Uani 1 1 d . . . H9 H 0.0648 0.1478 0.0907 0.044 Uiso 1 1 calc R . . C28 C 0.0677(3) -0.1854(5) 0.0815(4) 0.0322(19) Uani 1 1 d . . . C7 C 0.0889(4) -0.0242(5) 0.1338(5) 0.036(2) Uani 1 1 d . . . H7A H 0.0528 0.0019 0.1231 0.043 Uiso 1 1 calc R . . H7B H 0.1093 -0.0553 0.1826 0.043 Uiso 1 1 calc R . . C12 C 0.2232(3) 0.1023(5) 0.1724(4) 0.0309(18) Uani 1 1 d . . . C25 C 0.3830(4) -0.0494(5) -0.0181(5) 0.039(2) Uani 1 1 d . . . C18 C 0.3160(4) 0.1091(6) 0.0523(5) 0.041(2) Uani 1 1 d . . . C23 C 0.4873(4) -0.0564(5) 0.0743(5) 0.039(2) Uani 1 1 d . . . H23 H 0.5243 -0.0786 0.0910 0.046 Uiso 1 1 calc R . . C26 C 0.2997(3) 0.0733(5) 0.0965(5) 0.0339(19) Uani 1 1 d . . . C24 C 0.4372(4) -0.0838(5) 0.0042(5) 0.037(2) Uani 1 1 d . . . C11 C 0.1990(4) 0.1876(5) 0.1434(5) 0.037(2) Uani 1 1 d . . . H11 H 0.2223 0.2335 0.1441 0.044 Uiso 1 1 calc R . . C13 C 0.2872(4) 0.0842(6) 0.2031(5) 0.040(2) Uani 1 1 d . . . H13A H 0.3129 0.1086 0.2545 0.048 Uiso 1 1 calc R . . H13B H 0.2935 0.0188 0.2062 0.048 Uiso 1 1 calc R . . C2 C 0.0586(3) -0.2498(5) 0.0283(4) 0.0343(19) Uani 1 1 d . . . C19 C 0.3166(4) 0.0514(6) -0.0043(5) 0.050(2) Uani 1 1 d . . . H19A H 0.3035 0.0880 -0.0489 0.060 Uiso 1 1 calc R . . H19B H 0.2886 0.0018 -0.0203 0.060 Uiso 1 1 calc R . . C21 C 0.4284(4) 0.0385(6) 0.0967(5) 0.042(2) Uani 1 1 d . . . H21 H 0.4261 0.0793 0.1277 0.051 Uiso 1 1 calc R . . C17 C 0.3362(4) 0.1997(6) 0.0648(5) 0.049(2) Uani 1 1 d . . . H17 H 0.3456 0.2256 0.0340 0.059 Uiso 1 1 calc R . . C260 C 0.2197(4) -0.0319(6) 0.0349(6) 0.058(3) Uani 1 1 d . . . H26A H 0.2123 -0.0962 0.0324 0.088 Uiso 1 1 calc R . . H26B H 0.2055 -0.0099 -0.0149 0.088 Uiso 1 1 calc R . . H26C H 0.1995 -0.0007 0.0524 0.088 Uiso 1 1 calc R . . C270 C 0.2364(5) -0.0706(6) 0.2701(5) 0.059(3) Uani 1 1 d . . . H27A H 0.2496 -0.1328 0.2809 0.089 Uiso 1 1 calc R . . H27B H 0.2092 -0.0603 0.2828 0.089 Uiso 1 1 calc R . . H27C H 0.2699 -0.0307 0.2998 0.089 Uiso 1 1 calc R . . C280 C 0.0220(5) -0.2087(6) 0.1428(5) 0.057(3) Uani 1 1 d . . . H28A H 0.0298 -0.2301 0.1898 0.086 Uiso 1 1 calc R . . H28B H -0.0084 -0.2455 0.1013 0.086 Uiso 1 1 calc R . . H28C H 0.0091 -0.1464 0.1346 0.086 Uiso 1 1 calc R . . C250 C 0.3040(4) -0.1516(7) -0.0973(6) 0.066(3) Uani 1 1 d . . . H25A H 0.2699 -0.1594 -0.1492 0.099 Uiso 1 1 calc R . . H25B H 0.2917 -0.1500 -0.0643 0.099 Uiso 1 1 calc R . . H25C H 0.3309 -0.2015 -0.0831 0.099 Uiso 1 1 calc R . . C1S C 0.1383(5) 0.2518(7) 0.3149(6) 0.061(3) Uani 1 1 d . . . Cl1 Cl 0.1741(6) 0.2636(8) 0.4153(6) 0.093(4) Uani 0.63 1 d P A 1 Cl2 Cl 0.1390(7) 0.1364(7) 0.3001(8) 0.065(3) Uani 0.63 1 d P A 1 Cl3 Cl 0.0664(4) 0.2949(6) 0.2651(6) 0.128(3) Uani 0.63 1 d P A 1 Cl4 Cl 0.1760(9) 0.3100(15) 0.2908(16) 0.079(5) Uani 0.63 1 d P A 1 Cl22 Cl 0.101(2) 0.338(3) 0.331(3) 0.134(14) Uiso 0.12 1 d P A 3 Cl23 Cl 0.1144(14) 0.166(2) 0.2737(17) 0.063(10) Uiso 0.12 1 d P A 3 Cl24 Cl 0.196(5) 0.218(6) 0.425(5) 0.28(5) Uiso 0.12 1 d P A 3 Cl21 Cl 0.190(3) 0.323(4) 0.303(3) 0.028(9) Uiso 0.12 1 d P A 3 Cl11 Cl 0.194(3) 0.309(3) 0.301(4) 0.081(13) Uani 0.25 1 d P A 2 Cl12 Cl 0.1450(11) 0.2915(16) 0.3904(12) 0.075(8) Uani 0.25 1 d P A 2 Cl13 Cl 0.152(2) 0.129(2) 0.319(2) 0.130(16) Uani 0.25 1 d P A 2 Cl14 Cl 0.0671(8) 0.2670(14) 0.2282(10) 0.093(6) Uani 0.25 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 Br27 0.0471(6) 0.0387(5) 0.0690(7) 0.0101(5) 0.0345(6) 0.0108(4) Br28 0.0762(8) 0.0533(6) 0.0496(6) 0.0024(5) 0.0437(6) -0.0008(5) Br25 0.0437(6) 0.0704(7) 0.0506(6) -0.0162(5) 0.0217(5) -0.0034(5) Br26 0.0908(10) 0.0487(6) 0.1008(9) 0.0032(6) 0.0570(8) -0.0131(6) O28 0.055(4) 0.041(3) 0.036(3) 0.001(3) 0.031(3) 0.001(3) O27 0.044(4) 0.036(3) 0.038(3) 0.006(3) 0.021(3) 0.003(3) O25 0.039(4) 0.055(4) 0.037(3) -0.002(3) 0.018(3) 0.002(3) O26 0.047(4) 0.031(3) 0.057(4) -0.007(3) 0.027(4) -0.002(3) C27 0.042(5) 0.026(4) 0.027(4) 0.004(3) 0.024(4) 0.010(4) C1 0.047(6) 0.034(4) 0.040(5) -0.003(4) 0.026(5) 0.001(4) C5 0.028(5) 0.030(4) 0.043(5) -0.004(4) 0.018(4) -0.007(4) C3 0.040(6) 0.042(5) 0.039(5) -0.008(4) 0.024(5) 0.003(4) C6 0.023(5) 0.045(5) 0.029(5) -0.003(4) 0.015(4) -0.005(4) C15 0.032(5) 0.036(5) 0.048(5) -0.001(4) 0.024(5) 0.003(4) C8 0.033(5) 0.026(4) 0.025(4) -0.004(3) 0.016(4) -0.001(4) C10 0.049(6) 0.027(4) 0.046(5) 0.006(4) 0.034(5) 0.017(4) C4 0.034(5) 0.036(5) 0.036(5) 0.008(4) 0.019(4) 0.004(4) C16 0.039(6) 0.033(5) 0.064(6) 0.003(4) 0.031(5) 0.000(4) C20 0.038(5) 0.041(5) 0.037(5) 0.005(4) 0.025(5) 0.007(4) C14 0.028(5) 0.048(5) 0.038(5) 0.014(4) 0.020(4) 0.013(4) C22 0.043(6) 0.032(4) 0.035(5) -0.002(4) 0.024(5) -0.004(4) C9 0.024(5) 0.049(5) 0.036(5) -0.012(4) 0.016(4) 0.001(4) C28 0.025(5) 0.035(4) 0.029(4) -0.002(4) 0.012(4) -0.001(4) C7 0.030(5) 0.035(4) 0.042(5) -0.011(4) 0.021(4) -0.010(4) C12 0.027(5) 0.036(4) 0.032(4) -0.004(4) 0.019(4) 0.002(4) C25 0.045(6) 0.036(4) 0.035(5) 0.003(4) 0.023(5) 0.000(4) C18 0.029(5) 0.054(6) 0.041(5) 0.006(4) 0.022(5) 0.009(4) C23 0.028(5) 0.041(5) 0.050(6) 0.012(4) 0.024(5) 0.012(4) C26 0.024(5) 0.036(4) 0.036(5) 0.000(4) 0.014(4) 0.006(4) C24 0.044(6) 0.032(4) 0.038(5) 0.005(4) 0.027(5) 0.006(4) C11 0.037(5) 0.032(4) 0.044(5) -0.006(4) 0.026(5) -0.001(4) C13 0.029(5) 0.044(5) 0.037(5) -0.009(4) 0.013(4) -0.005(4) C2 0.025(5) 0.036(4) 0.032(5) 0.005(4) 0.012(4) 0.002(4) C19 0.052(6) 0.067(6) 0.041(5) -0.002(5) 0.032(5) 0.008(5) C21 0.047(6) 0.040(5) 0.048(6) -0.004(4) 0.033(5) 0.008(4) C17 0.045(6) 0.060(6) 0.058(6) 0.016(5) 0.039(5) 0.012(5) C260 0.059(7) 0.050(6) 0.066(7) -0.011(5) 0.037(6) -0.008(5) C270 0.064(7) 0.052(6) 0.055(6) 0.015(5) 0.031(6) 0.011(5) C280 0.078(8) 0.052(6) 0.061(7) -0.007(5) 0.052(7) -0.012(5) C250 0.044(7) 0.073(7) 0.064(7) -0.004(6) 0.021(6) -0.022(6) C1S 0.062(7) 0.054(6) 0.074(7) 0.011(5) 0.045(6) 0.003(5) Cl1 0.142(10) 0.081(6) 0.054(5) -0.013(4) 0.057(6) -0.032(6) Cl2 0.079(6) 0.047(4) 0.085(5) -0.018(4) 0.058(5) -0.005(4) Cl3 0.085(5) 0.118(7) 0.168(9) 0.072(7) 0.068(7) 0.046(5) Cl4 0.103(13) 0.078(5) 0.096(10) -0.018(6) 0.081(11) -0.034(8) Cl11 0.08(3) 0.046(16) 0.15(2) -0.010(12) 0.09(2) -0.019(14) Cl12 0.121(19) 0.080(15) 0.055(14) -0.047(11) 0.069(15) -0.067(14) Cl13 0.14(3) 0.113(18) 0.17(3) 0.059(15) 0.11(3) -0.006(15) Cl14 0.053(9) 0.147(15) 0.078(10) -0.026(9) 0.039(8) -0.005(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 Br27 C10 1.893(7) . ? Br28 C4 1.920(8) . ? Br25 C22 1.911(8) . ? Br26 C16 1.888(8) . ? O28 C28 1.375(9) . ? O28 C280 1.430(10) . ? O27 C27 1.373(8) . ? O27 C270 1.409(10) . ? O25 C25 1.390(10) . ? O25 C250 1.411(10) . ? O26 C26 1.364(9) . ? O26 C260 1.426(11) . ? C27 C8 1.391(10) . ? C27 C12 1.392(11) . ? C1 C24 1.509(11) 7_545 ? C1 C2 1.521(11) . ? C5 C6 1.372(11) . ? C5 C4 1.379(11) . ? C3 C4 1.373(11) . ? C3 C2 1.383(11) . ? C6 C28 1.392(10) . ? C6 C7 1.521(10) . ? C15 C16 1.386(12) . ? C15 C14 1.392(11) . ? C8 C9 1.368(11) . ? C8 C7 1.507(10) . ? C10 C11 1.377(11) . ? C10 C9 1.411(11) . ? C16 C17 1.387(12) . ? C20 C21 1.390(12) . ? C20 C25 1.399(11) . ? C20 C19 1.524(11) . ? C14 C26 1.413(11) . ? C14 C13 1.515(11) . ? C22 C21 1.375(11) . ? C22 C23 1.382(11) . ? C28 C2 1.393(11) . ? C12 C11 1.384(10) . ? C12 C13 1.520(11) . ? C25 C24 1.382(11) . ? C18 C26 1.384(11) . ? C18 C17 1.404(12) . ? C18 C19 1.498(11) . ? C23 C24 1.387(11) . ? C24 C1 1.509(11) 7_545 ? C1S Cl23 1.45(3) . ? C1S Cl12 1.64(2) . ? C1S Cl4 1.66(2) . ? C1S Cl2 1.724(13) . ? C1S Cl3 1.744(12) . ? C1S Cl14 1.77(2) . ? C1S Cl22 1.79(4) . ? C1S Cl1 1.791(15) . ? C1S Cl13 1.83(4) . ? C1S Cl21 1.91(7) . ? C1S Cl24 2.00(10) . ? C1S Cl11 1.94(5) . ? 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 C28 O28 C280 113.3(6) . . ? C27 O27 C270 114.9(6) . . ? C25 O25 C250 115.3(7) . . ? C26 O26 C260 116.6(6) . . ? O27 C27 C8 118.1(7) . . ? O27 C27 C12 120.2(7) . . ? C8 C27 C12 121.5(7) . . ? C24 C1 C2 115.5(7) 7_545 . ? C6 C5 C4 119.9(7) . . ? C4 C3 C2 119.1(7) . . ? C5 C6 C28 118.7(7) . . ? C5 C6 C7 120.1(7) . . ? C28 C6 C7 121.0(7) . . ? C16 C15 C14 119.7(8) . . ? C9 C8 C27 119.7(7) . . ? C9 C8 C7 119.8(7) . . ? C27 C8 C7 120.5(7) . . ? C11 C10 C9 120.7(7) . . ? C11 C10 Br27 119.3(6) . . ? C9 C10 Br27 120.0(6) . . ? C3 C4 C5 121.9(7) . . ? C3 C4 Br28 119.4(6) . . ? C5 C4 Br28 118.6(6) . . ? C17 C16 C15 120.9(8) . . ? C17 C16 Br26 119.9(7) . . ? C15 C16 Br26 119.1(7) . . ? C21 C20 C25 118.5(8) . . ? C21 C20 C19 122.3(7) . . ? C25 C20 C19 119.1(8) . . ? C15 C14 C26 119.3(7) . . ? C15 C14 C13 120.9(7) . . ? C26 C14 C13 119.8(8) . . ? C21 C22 C23 121.9(8) . . ? C21 C22 Br25 119.7(6) . . ? C23 C22 Br25 118.3(7) . . ? C8 C9 C10 119.1(7) . . ? O28 C28 C6 119.7(7) . . ? O28 C28 C2 118.9(7) . . ? C6 C28 C2 121.3(7) . . ? C8 C7 C6 112.1(6) . . ? C11 C12 C27 118.5(7) . . ? C11 C12 C13 119.3(7) . . ? C27 C12 C13 122.1(7) . . ? C24 C25 O25 119.4(7) . . ? C24 C25 C20 122.4(8) . . ? O25 C25 C20 117.9(8) . . ? C26 C18 C17 118.9(8) . . ? C26 C18 C19 121.2(8) . . ? C17 C18 C19 119.7(8) . . ? C22 C23 C24 120.0(8) . . ? O26 C26 C18 119.5(7) . . ? O26 C26 C14 119.5(7) . . ? C18 C26 C14 120.9(8) . . ? C25 C24 C23 118.0(7) . . ? C25 C24 C1 121.9(8) . 7_545 ? C23 C24 C1 120.1(8) . 7_545 ? C10 C11 C12 120.3(8) . . ? C14 C13 C12 113.7(7) . . ? C3 C2 C28 119.0(7) . . ? C3 C2 C1 122.3(7) . . ? C28 C2 C1 118.7(7) . . ? C18 C19 C20 113.4(7) . . ? C22 C21 C20 119.2(7) . . ? C16 C17 C18 120.1(8) . . ? Cl23 C1S Cl12 131.3(16) . . ? Cl23 C1S Cl4 113.5(16) . . ? Cl12 C1S Cl4 114.2(13) . . ? Cl23 C1S Cl2 24.6(11) . . ? Cl12 C1S Cl2 121.7(11) . . ? Cl4 C1S Cl2 111.6(10) . . ? Cl23 C1S Cl3 89.3(14) . . ? Cl12 C1S Cl3 84.4(10) . . ? Cl4 C1S Cl3 109.3(10) . . ? Cl2 C1S Cl3 112.0(9) . . ? Cl23 C1S Cl14 68.6(14) . . ? Cl12 C1S Cl14 114.2(11) . . ? Cl4 C1S Cl14 97.2(12) . . ? Cl2 C1S Cl14 93.2(10) . . ? Cl3 C1S Cl14 29.8(5) . . ? Cl23 C1S Cl22 128(2) . . ? Cl12 C1S Cl22 45.1(17) . . ? Cl4 C1S Cl22 104.1(17) . . ? Cl2 C1S Cl22 143.0(16) . . ? Cl3 C1S Cl22 44.0(17) . . ? Cl14 C1S Cl22 72.7(19) . . ? Cl23 C1S Cl1 123.7(13) . . ? Cl12 C1S Cl1 25.7(9) . . ? Cl4 C1S Cl1 109.2(11) . . ? Cl2 C1S Cl1 105.1(8) . . ? Cl3 C1S Cl1 109.5(8) . . ? Cl14 C1S Cl1 138.7(9) . . ? Cl22 C1S Cl1 70.5(18) . . ? Cl23 C1S Cl13 36(2) . . ? Cl12 C1S Cl13 113.6(15) . . ? Cl4 C1S Cl13 111.7(15) . . ? Cl2 C1S Cl13 11.5(18) . . ? Cl3 C1S Cl13 121.2(15) . . ? Cl14 C1S Cl13 104.4(16) . . ? Cl22 C1S Cl13 144.1(19) . . ? Cl1 C1S Cl13 94.8(14) . . ? Cl23 C1S Cl21 120(2) . . ? Cl12 C1S Cl21 107(2) . . ? Cl4 C1S Cl21 8(2) . . ? Cl2 C1S Cl21 115(2) . . ? Cl3 C1S Cl21 113(2) . . ? Cl14 C1S Cl21 104.4(18) . . ? Cl22 C1S Cl21 102(3) . . ? Cl1 C1S Cl21 100.8(17) . . ? Cl13 C1S Cl21 113(2) . . ? Cl23 C1S Cl24 106(3) . . ? Cl12 C1S Cl24 50(3) . . ? Cl4 C1S Cl24 107(3) . . ? Cl2 C1S Cl24 84(3) . . ? Cl3 C1S Cl24 131(3) . . ? Cl14 C1S Cl24 156(3) . . ? Cl22 C1S Cl24 96(3) . . ? Cl1 C1S Cl24 25(3) . . ? Cl13 C1S Cl24 72(3) . . ? Cl21 C1S Cl24 99(3) . . ? Cl23 C1S Cl11 113.5(19) . . ? Cl12 C1S Cl11 111.7(18) . . ? Cl4 C1S Cl11 10(3) . . ? Cl2 C1S Cl11 107.3(15) . . ? Cl3 C1S Cl11 119(2) . . ? Cl14 C1S Cl11 107(2) . . ? Cl22 C1S Cl11 110(2) . . ? Cl1 C1S Cl11 103(2) . . ? Cl13 C1S Cl11 105.6(19) . . ? Cl21 C1S Cl11 8(3) . . ? Cl24 C1S Cl11 97(4) . . ? 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 C1 C2 C28 C6 175.8(7) . . . . ? C2 C28 C6 C7 -173.9(7) . . . . ? C28 C6 C7 C8 144.4(8) . . . . ? C6 C7 C8 C27 -72.6(9) . . . . ? C7 C8 C27 C12 177.9(7) . . . . ? C8 C27 C12 C13 -177.9(7) . . . . ? C27 C12 C13 C14 136.1(8) . . . . ? C12 C13 C14 C26 -92.1(9) . . . . ? C13 C14 C26 C18 -179.3(7) . . . . ? C14 C26 C18 C19 173.6(8) . . . . ? C26 C18 C19 C20 -95.5(10) . . . . ? C18 C19 C20 C25 174.9(8) . . . . ? C19 C20 C25 C24 175.8(8) . . . . ? C20 C25 C24 C1 180.0(7) . . . 7_545 ? C20 C25 C24 C1 180.0(7) . . . 7_545 ? C25 C24 C1 C2 -92.8(10) . . 7_545 7_545 ? C24 C1 C2 C28 165.3(7) . 7_545 7_545 7_545 ? C1 C2 C28 C6 -175.8(7) 7_545 7_545 7_545 7_545 ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.783 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.162