# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'A. W. Coleman' 'Oksana Danylyuk' 'Bernard Bertino Ghera' 'Helene Parrot-Lopez' 'Florent Perret' 'Kinga Suwinska' _publ_contact_author_name 'A. W. Coleman' _publ_contact_author_address ; CNRS Institute de Biologie et Chimie des Proteines (IBCP) 7, Passage du Vercors Lyon Cedex 7 69367 FRANCE ; _publ_contact_author_email AW.COLEMAN@IBCP.FR _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Synthesis, solid state structures and interfacial properties of new para- phosphonato-O-alkyloxy-calix[8]arene derivatives ; data_awc8040_ks _database_code_depnum_ccdc_archive 'CCDC 637889' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common awc8040_KS _chemical_melting_point ? _chemical_formula_moiety 'C64 H56 Br8 O8 . H2 O1' _chemical_formula_sum 'C64 H56 Br8 O9' _chemical_formula_weight 1608.37 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' 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7192(7) _cell_length_b 26.300(1) _cell_length_c 15.251(2) _cell_angle_alpha 90.000(5) _cell_angle_beta 91.521(6) _cell_angle_gamma 90.000(4) _cell_volume 3496.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 343537 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 23.26 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 4.637 _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 KappaApexII _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 342487 _diffrn_reflns_av_R_equivalents 0.0799 _diffrn_reflns_av_sigmaI/netI 0.0816 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 23.32 _reflns_number_total 4980 _reflns_number_gt 2800 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect data collection software (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _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^)+(0.1639P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4980 _refine_ls_number_parameters 386 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1470 _refine_ls_R_factor_gt 0.0850 _refine_ls_wR_factor_ref 0.2693 _refine_ls_wR_factor_gt 0.2370 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 C9 C 0.3152(13) -0.0213(4) 0.1285(6) 0.055(3) Uani 1 1 d . . . C10 C 0.3670(14) -0.0580(5) 0.1823(9) 0.079(4) Uani 1 1 d . . . C11 C 0.5142(15) -0.0537(5) 0.2217(9) 0.086(4) Uani 1 1 d . . . H11 H 0.5510 -0.0788 0.2599 0.103 Uiso 1 1 calc R . . C12 C 0.6068(14) -0.0104(4) 0.2021(8) 0.066(3) Uani 1 1 d . . . C13 C 0.5467(14) 0.0263(4) 0.1451(7) 0.061(3) Uani 1 1 d . . . H13 H 0.6060 0.0546 0.1321 0.073 Uiso 1 1 calc R . . C14 C 0.4058(14) 0.0221(4) 0.1086(7) 0.055(3) Uani 1 1 d . . . C15 C 0.3430(14) 0.0630(4) 0.0475(7) 0.067(3) Uani 1 1 d . . . H15A H 0.3773 0.0564 -0.0115 0.080 Uiso 1 1 calc R . . H15B H 0.2318 0.0615 0.0462 0.080 Uiso 1 1 calc R . . C16 C 0.3368(13) 0.1366(4) 0.1489(7) 0.058(3) Uani 1 1 d . . . C17 C 0.3937(15) 0.1152(4) 0.0753(7) 0.067(3) Uani 1 1 d . . . C18 C 0.5009(14) 0.1433(5) 0.0272(7) 0.067(3) Uani 1 1 d . . . H18 H 0.5390 0.1299 -0.0243 0.081 Uiso 1 1 calc R . . C19 C 0.5478(14) 0.1890(5) 0.0553(7) 0.072(3) Uani 1 1 d . . . C20 C 0.4948(15) 0.2112(4) 0.1327(7) 0.069(3) Uani 1 1 d . . . H20 H 0.5312 0.2428 0.1515 0.083 Uiso 1 1 calc R . . C21 C 0.3854(13) 0.1847(4) 0.1811(7) 0.059(3) Uani 1 1 d . . . C22 C 0.3330(14) 0.2054(4) 0.2660(7) 0.065(3) Uani 1 1 d . . . H22A H 0.2826 0.1784 0.2976 0.078 Uiso 1 1 calc R . . H22B H 0.2572 0.2316 0.2538 0.078 Uiso 1 1 calc R . . C23 C 0.5484(15) 0.1982(5) 0.3807(7) 0.067(3) Uani 1 1 d . . . C24 C 0.4573(13) 0.2274(5) 0.3243(8) 0.066(3) Uani 1 1 d . . . C25 C 0.4858(14) 0.2815(4) 0.3210(7) 0.064(3) Uani 1 1 d . . . H25 H 0.4271 0.3021 0.2836 0.077 Uiso 1 1 calc R . . C26 C 0.5996(14) 0.3022(4) 0.3732(8) 0.065(3) Uani 1 1 d . . . C27 C 0.6855(14) 0.2727(5) 0.4312(8) 0.071(3) Uani 1 1 d . . . H27 H 0.7603 0.2877 0.4673 0.085 Uiso 1 1 calc R . . C28 C 0.6599(15) 0.2206(5) 0.4356(8) 0.072(3) Uani 1 1 d . . . C29 C 0.7573(16) 0.1906(5) 0.5009(8) 0.083(4) Uani 1 1 d . . . H29A H 0.8557 0.2073 0.5095 0.100 Uiso 1 1 calc R . . H29B H 0.7758 0.1569 0.4776 0.100 Uiso 1 1 calc R . . C30 C 0.7343(17) 0.1468(5) 0.6471(9) 0.079(4) Uani 1 1 d . A . C31 C 0.6787(17) 0.1858(5) 0.5897(7) 0.080(4) Uani 1 1 d . . . C32 C 0.5652(16) 0.2169(4) 0.6157(8) 0.071(3) Uani 1 1 d . . . H32 H 0.5281 0.2419 0.5777 0.086 Uiso 1 1 calc R . . C33 C 0.5034(16) 0.2122(5) 0.6976(7) 0.081(4) Uani 1 1 d . . . C34 C 0.5549(17) 0.1743(6) 0.7544(9) 0.087(4) Uani 1 1 d . . . H34 H 0.5096 0.1705 0.8085 0.105 Uiso 1 1 calc R . . C35 C 0.6694(17) 0.1429(5) 0.7323(8) 0.078(4) Uani 1 1 d . . . C36 C 0.7332(16) 0.1058(6) 0.7997(9) 0.102(5) Uani 1 1 d . . . H36A H 0.7494 0.1238 0.8547 0.123 Uiso 1 1 calc R . . H36B H 0.8328 0.0943 0.7808 0.123 Uiso 1 1 calc R . . C37 C 0.1526(16) -0.0471(5) 0.0129(10) 0.089(4) Uani 1 1 d . . . H37A H 0.2010 -0.0799 0.0141 0.134 Uiso 1 1 calc R . . H37B H 0.2008 -0.0259 -0.0296 0.134 Uiso 1 1 calc R . . H37C H 0.0458 -0.0509 -0.0026 0.134 Uiso 1 1 calc R . . C38 C 0.0815(19) 0.1222(6) 0.1756(10) 0.104(5) Uani 1 1 d . . . H38A H 0.0569 0.1129 0.1160 0.157 Uiso 1 1 calc R . . H38B H 0.0688 0.1582 0.1828 0.157 Uiso 1 1 calc R . . H38C H 0.0144 0.1045 0.2142 0.157 Uiso 1 1 calc R . . C39 C 0.6076(19) 0.1165(5) 0.3349(10) 0.098(5) Uani 1 1 d . . . H39A H 0.6153 0.0829 0.3595 0.147 Uiso 1 1 calc R . . H39B H 0.7082 0.1311 0.3316 0.147 Uiso 1 1 calc R . . H39C H 0.5616 0.1145 0.2771 0.147 Uiso 1 1 calc R . . C40A C 1.009(2) 0.1246(10) 0.6218(17) 0.102(11) Uani 0.58(3) 1 d PD A 1 H40A H 1.0284 0.1528 0.5839 0.153 Uiso 0.58(3) 1 calc PR A 1 H40B H 1.0585 0.0948 0.6001 0.153 Uiso 0.58(3) 1 calc PR A 1 H40C H 1.0474 0.1321 0.6799 0.153 Uiso 0.58(3) 1 calc PR A 1 C40B C 0.810(4) 0.0645(10) 0.604(3) 0.14(2) Uani 0.42(3) 1 d PD A 2 H40D H 0.7311 0.0532 0.6421 0.206 Uiso 0.42(3) 1 calc PR A 2 H40E H 0.8993 0.0434 0.6124 0.206 Uiso 0.42(3) 1 calc PR A 2 H40F H 0.7743 0.0622 0.5441 0.206 Uiso 0.42(3) 1 calc PR A 2 Br1 Br 0.80328(15) -0.00391(5) 0.25163(10) 0.0851(6) Uani 1 1 d . . . Br2 Br 0.64293(15) 0.37253(5) 0.36408(9) 0.0787(6) Uani 1 1 d . . . Br3 Br 0.35377(19) 0.25821(6) 0.73305(9) 0.0996(6) Uani 1 1 d . . . Br4 Br 0.6920(2) 0.22610(7) -0.01311(9) 0.1087(7) Uani 1 1 d . . . O5 O 0.1681(10) -0.0238(3) 0.0986(5) 0.078(2) Uani 1 1 d . . . O6 O 0.2347(10) 0.1087(3) 0.1961(5) 0.068(2) Uani 1 1 d . . . O7 O 0.5159(11) 0.1472(3) 0.3886(5) 0.084(2) Uani 1 1 d . . . O8 O 0.8491(14) 0.1160(6) 0.6242(8) 0.127(4) Uani 1 1 d D . . O1W O 0.881(3) -0.0244(12) 0.522(2) 0.162(11) Uani 0.50 1 d P . . 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 C9 0.048(7) 0.077(8) 0.039(6) 0.015(6) -0.016(5) 0.004(6) C10 0.066(9) 0.093(9) 0.079(9) 0.016(8) 0.012(7) -0.011(7) C11 0.076(9) 0.091(9) 0.090(10) 0.048(8) -0.023(8) -0.013(8) C12 0.076(8) 0.055(7) 0.067(7) 0.007(6) 0.007(6) 0.012(6) C13 0.077(9) 0.039(6) 0.068(7) -0.002(6) 0.017(7) -0.003(6) C14 0.063(8) 0.050(6) 0.053(6) 0.007(5) -0.001(6) 0.004(6) C15 0.087(8) 0.063(7) 0.051(7) 0.011(6) 0.005(6) 0.012(6) C16 0.066(7) 0.059(7) 0.049(7) -0.004(6) -0.002(6) 0.007(6) C17 0.105(9) 0.056(7) 0.040(6) -0.002(6) -0.011(6) 0.020(7) C18 0.088(9) 0.073(8) 0.042(6) 0.010(6) 0.004(6) -0.008(7) C19 0.086(8) 0.090(9) 0.039(7) 0.008(6) -0.007(6) -0.021(7) C20 0.104(9) 0.052(7) 0.050(7) -0.003(6) -0.010(7) 0.007(7) C21 0.072(7) 0.046(6) 0.058(7) 0.007(6) -0.004(6) 0.003(6) C22 0.081(8) 0.064(7) 0.050(7) -0.006(6) 0.004(6) 0.009(6) C23 0.086(9) 0.071(8) 0.045(7) 0.006(6) 0.003(7) 0.005(7) C24 0.066(8) 0.075(8) 0.058(7) -0.002(6) 0.017(7) -0.001(6) C25 0.080(8) 0.055(7) 0.058(7) -0.001(6) -0.002(7) 0.010(6) C26 0.084(8) 0.050(6) 0.063(7) -0.010(6) 0.015(7) 0.001(6) C27 0.077(8) 0.079(9) 0.056(7) 0.005(6) 0.011(6) 0.031(7) C28 0.096(9) 0.072(8) 0.048(7) 0.013(6) 0.002(7) 0.016(7) C29 0.110(10) 0.076(8) 0.062(8) 0.006(6) -0.001(7) 0.012(7) C30 0.085(10) 0.066(8) 0.083(10) 0.005(7) -0.025(8) -0.006(7) C31 0.123(11) 0.071(8) 0.045(7) 0.025(6) -0.001(7) -0.013(8) C32 0.108(10) 0.051(7) 0.055(8) 0.005(6) 0.006(7) 0.003(7) C33 0.119(11) 0.083(9) 0.041(7) 0.028(6) -0.017(7) -0.038(8) C34 0.086(10) 0.108(11) 0.068(9) 0.004(9) 0.004(8) -0.043(9) C35 0.097(10) 0.079(9) 0.057(8) 0.029(7) -0.004(8) -0.016(8) C36 0.086(10) 0.140(13) 0.079(9) 0.049(9) -0.011(8) -0.030(9) C37 0.088(10) 0.078(9) 0.100(11) 0.005(8) -0.016(8) -0.010(7) C38 0.104(13) 0.131(13) 0.080(10) -0.025(9) 0.025(9) -0.020(10) C39 0.145(13) 0.056(7) 0.093(10) -0.007(7) 0.007(9) 0.033(8) C40A 0.10(3) 0.11(2) 0.094(19) 0.006(15) -0.025(15) -0.017(15) C40B 0.12(3) 0.11(4) 0.19(5) 0.08(3) 0.04(3) 0.05(3) Br1 0.0789(10) 0.0664(9) 0.1091(12) 0.0123(7) -0.0141(8) -0.0034(6) Br2 0.0969(11) 0.0624(8) 0.0760(9) -0.0088(6) -0.0125(7) 0.0077(6) Br3 0.1264(14) 0.1073(12) 0.0669(10) -0.0027(8) 0.0327(9) -0.0230(9) Br4 0.1389(15) 0.1358(14) 0.0519(9) 0.0040(8) 0.0139(8) -0.0573(11) O5 0.091(7) 0.085(6) 0.059(5) 0.016(5) 0.007(5) 0.008(5) O6 0.075(6) 0.064(5) 0.067(5) -0.004(4) 0.023(4) -0.006(4) O7 0.126(7) 0.054(5) 0.071(5) 0.002(4) 0.004(5) -0.004(5) O8 0.088(9) 0.168(13) 0.125(9) 0.084(9) 0.014(7) 0.029(9) O1W 0.108(17) 0.18(2) 0.20(3) -0.07(2) 0.064(18) -0.009(16) _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 C9 C10 1.337(16) . ? C9 O5 1.352(12) . ? C9 C14 1.425(15) . ? C10 C11 1.407(16) . ? C10 C36 1.560(18) 3_656 ? C11 C12 1.433(17) . ? C11 H11 0.9300 . ? C12 C13 1.392(15) . ? C12 Br1 1.862(12) . ? C13 C14 1.340(15) . ? C13 H13 0.9300 . ? C14 C15 1.515(15) . ? C15 C17 1.500(16) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.361(15) . ? C16 O6 1.372(13) . ? C16 C21 1.418(15) . ? C17 C18 1.412(16) . ? C18 C19 1.338(16) . ? C18 H18 0.9300 . ? C19 C20 1.406(16) . ? C19 Br4 1.921(11) . ? C20 C21 1.407(16) . ? C20 H20 0.9300 . ? C21 C22 1.488(15) . ? C22 C24 1.500(16) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 O7 1.376(14) . ? C23 C24 1.388(16) . ? C23 C28 1.396(17) . ? C24 C25 1.446(16) . ? C25 C26 1.369(16) . ? C25 H25 0.9300 . ? C26 C27 1.381(16) . ? C26 Br2 1.893(11) . ? C27 C28 1.391(17) . ? C27 H27 0.9300 . ? C28 C29 1.514(17) . ? C29 C31 1.538(18) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 O8 1.342(17) . ? C30 C31 1.426(17) . ? C30 C35 1.434(19) . ? C31 C32 1.351(17) . ? C32 C33 1.379(16) . ? C32 H32 0.9300 . ? C33 C34 1.388(18) . ? C33 Br3 1.869(15) . ? C34 C35 1.345(18) . ? C34 H34 0.9300 . ? C35 C36 1.514(18) . ? C36 C10 1.560(18) 3_656 ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 O5 1.446(16) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 O6 1.409(17) . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 O7 1.414(14) . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40A O8 1.411(16) . ? C40A H40A 0.9600 . ? C40A H40B 0.9600 . ? C40A H40C 0.9600 . ? C40B O8 1.426(19) . ? C40B H40D 0.9600 . ? C40B H40E 0.9600 . ? C40B H40F 0.9600 . ? 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 C10 C9 O5 118.2(10) . . ? C10 C9 C14 121.9(11) . . ? O5 C9 C14 119.6(10) . . ? C9 C10 C11 119.6(11) . . ? C9 C10 C36 120.5(12) . 3_656 ? C11 C10 C36 119.8(11) . 3_656 ? C10 C11 C12 119.1(11) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C13 C12 C11 118.5(11) . . ? C13 C12 Br1 121.1(9) . . ? C11 C12 Br1 120.4(9) . . ? C14 C13 C12 121.9(10) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C9 119.0(10) . . ? C13 C14 C15 120.6(10) . . ? C9 C14 C15 120.4(11) . . ? C17 C15 C14 112.1(10) . . ? C17 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C17 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C17 C16 O6 117.9(10) . . ? C17 C16 C21 122.9(11) . . ? O6 C16 C21 119.1(9) . . ? C16 C17 C18 118.2(11) . . ? C16 C17 C15 120.1(11) . . ? C18 C17 C15 121.8(10) . . ? C19 C18 C17 120.4(11) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 122.6(11) . . ? C18 C19 Br4 118.8(9) . . ? C20 C19 Br4 118.6(9) . . ? C19 C20 C21 118.4(10) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C20 C21 C16 117.5(10) . . ? C20 C21 C22 120.2(10) . . ? C16 C21 C22 122.2(10) . . ? C21 C22 C24 115.1(10) . . ? C21 C22 H22A 108.5 . . ? C24 C22 H22A 108.5 . . ? C21 C22 H22B 108.5 . . ? C24 C22 H22B 108.5 . . ? H22A C22 H22B 107.5 . . ? O7 C23 C24 118.5(11) . . ? O7 C23 C28 120.0(11) . . ? C24 C23 C28 121.0(11) . . ? C23 C24 C25 118.1(11) . . ? C23 C24 C22 123.2(11) . . ? C25 C24 C22 118.7(11) . . ? C26 C25 C24 119.6(11) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C27 121.4(11) . . ? C25 C26 Br2 119.2(9) . . ? C27 C26 Br2 119.3(10) . . ? C26 C27 C28 120.0(12) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C27 C28 C23 119.8(11) . . ? C27 C28 C29 117.3(12) . . ? C23 C28 C29 122.9(12) . . ? C28 C29 C31 111.5(11) . . ? C28 C29 H29A 109.3 . . ? C31 C29 H29A 109.3 . . ? C28 C29 H29B 109.3 . . ? C31 C29 H29B 109.3 . . ? H29A C29 H29B 108.0 . . ? O8 C30 C31 121.2(13) . . ? O8 C30 C35 120.5(12) . . ? C31 C30 C35 118.2(14) . . ? C32 C31 C30 119.6(12) . . ? C32 C31 C29 123.8(11) . . ? C30 C31 C29 116.5(13) . . ? C31 C32 C33 121.3(12) . . ? C31 C32 H32 119.4 . . ? C33 C32 H32 119.4 . . ? C32 C33 C34 120.1(14) . . ? C32 C33 Br3 119.8(10) . . ? C34 C33 Br3 120.1(10) . . ? C35 C34 C33 121.0(13) . . ? C35 C34 H34 119.5 . . ? C33 C34 H34 119.5 . . ? C34 C35 C30 119.7(12) . . ? C34 C35 C36 119.2(13) . . ? C30 C35 C36 121.0(14) . . ? C35 C36 C10 116.2(11) . 3_656 ? C35 C36 H36A 108.2 . . ? C10 C36 H36A 108.2 3_656 . ? C35 C36 H36B 108.2 . . ? C10 C36 H36B 108.2 3_656 . ? H36A C36 H36B 107.4 . . ? O5 C37 H37A 109.5 . . ? O5 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O5 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O6 C38 H38A 109.5 . . ? O6 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O6 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O7 C39 H39A 109.5 . . ? O7 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O7 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? O8 C40A H40A 109.5 . . ? O8 C40A H40B 109.5 . . ? O8 C40A H40C 109.5 . . ? O8 C40B H40D 109.5 . . ? O8 C40B H40E 109.5 . . ? H40D C40B H40E 109.5 . . ? O8 C40B H40F 109.5 . . ? H40D C40B H40F 109.5 . . ? H40E C40B H40F 109.5 . . ? C9 O5 C37 113.0(9) . . ? C16 O6 C38 112.0(9) . . ? C23 O7 C39 112.7(9) . . ? C30 O8 C40A 130.7(19) . . ? C30 O8 C40B 117.1(18) . . ? C40A O8 C40B 112(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 23.32 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.193 _refine_diff_density_min -0.827 _refine_diff_density_rms 0.138 # Attachment 'awc8044.cif' data_awc8044 _database_code_depnum_ccdc_archive 'CCDC 637890' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common awc8044 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C88 H104 Br8 O8' _chemical_formula_weight 1928.99 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' _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 15.8507(3) _cell_length_b 16.6896(3) _cell_length_c 18.4507(4) _cell_angle_alpha 107.079(1) _cell_angle_beta 90.820(1) _cell_angle_gamma 114.725(1) _cell_volume 4186.09(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 68169 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour transparent _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 3.886 _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 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 KappaApexII _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 68169 _diffrn_reflns_av_R_equivalents 0.0927 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.47 _reflns_number_total 18835 _reflns_number_gt 13533 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect data collection software (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _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^)+(0.0463P)^2^+39.1913P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 18835 _refine_ls_number_parameters 944 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.119 _refine_ls_R_factor_gt 0.079 _refine_ls_wR_factor_ref 0.181 _refine_ls_wR_factor_gt 0.164 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.07 _refine_ls_shift/su_max 0.068 _refine_ls_shift/su_mean 0.004 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 0.0777(4) 0.3539(4) 0.1678(3) 0.0190(13) Uani 1 1 d . . . C2 C 0.0492(5) 0.3126(4) 0.0880(4) 0.0214(13) Uani 1 1 d . . . C3 C 0.0743(5) 0.2420(5) 0.0495(4) 0.0237(14) Uani 1 1 d . . . H3 H 0.0558 0.2124 -0.0044 0.028 Uiso 1 1 calc R . . C4 C 0.1254(5) 0.2157(5) 0.0897(4) 0.0255(14) Uani 1 1 d . . . C5 C 0.1530(5) 0.2553(4) 0.1685(4) 0.0227(14) Uani 1 1 d . . . H5 H 0.1876 0.2348 0.1950 0.027 Uiso 1 1 calc R . . C6 C 0.1287(4) 0.3261(4) 0.2086(4) 0.0211(13) Uani 1 1 d . . . C7 C -0.0295(5) 0.4098(5) 0.2292(4) 0.0326(17) Uani 1 1 d . . . H7A H -0.0434 0.3685 0.2609 0.039 Uiso 1 1 calc R . . H7B H -0.0786 0.3783 0.1832 0.039 Uiso 1 1 calc R . . C8 C -0.0273(6) 0.5033(6) 0.2753(5) 0.043(2) Uani 1 1 d . . . H8A H -0.0001 0.5481 0.2471 0.052 Uiso 1 1 calc R . . H8B H -0.0926 0.4944 0.2799 0.052 Uiso 1 1 calc R . . C9 C 0.0277(9) 0.5428(9) 0.3523(6) 0.084(4) Uani 1 1 d . . . H9A H 0.0924 0.5499 0.3480 0.101 Uiso 1 1 calc R . . H9B H -0.0009 0.4995 0.3814 0.101 Uiso 1 1 calc R . . C10 C 0.0313(11) 0.6390(10) 0.3960(8) 0.116(6) Uani 1 1 d . . . H10A H 0.0651 0.6836 0.3699 0.173 Uiso 1 1 calc R . . H10B H 0.0640 0.6614 0.4486 0.173 Uiso 1 1 calc R . . H10C H -0.0329 0.6328 0.3973 0.173 Uiso 1 1 calc R . . C11 C 0.1597(5) 0.3763(5) 0.2952(4) 0.0255(15) Uani 1 1 d . . . H11A H 0.2035 0.4426 0.3044 0.031 Uiso 1 1 calc R . . H11B H 0.1038 0.3746 0.3193 0.031 Uiso 1 1 calc R . . C12 C 0.1546(4) 0.2543(4) 0.3530(3) 0.0183(12) Uani 1 1 d . . . C13 C 0.2073(5) 0.3342(4) 0.3335(4) 0.0213(13) Uani 1 1 d . . . C14 C 0.3051(5) 0.3720(4) 0.3478(3) 0.0209(13) Uani 1 1 d . . . H14 H 0.3428 0.4276 0.3372 0.025 Uiso 1 1 calc R . . C15 C 0.3468(4) 0.3277(4) 0.3775(4) 0.0201(13) Uani 1 1 d . . . C16 C 0.2949(4) 0.2457(4) 0.3917(3) 0.0176(12) Uani 1 1 d . . . H16 H 0.3256 0.2154 0.4096 0.021 Uiso 1 1 calc R . . C17 C 0.1977(4) 0.2078(4) 0.3795(3) 0.0168(12) Uani 1 1 d . . . C18 C 0.0225(5) 0.2434(5) 0.4137(4) 0.0302(16) Uani 1 1 d . . . H18A H 0.0432 0.3117 0.4344 0.036 Uiso 1 1 calc R . . H18B H 0.0467 0.2244 0.4521 0.036 Uiso 1 1 calc R . . C19 C -0.0858(5) 0.1912(5) 0.3964(4) 0.0310(16) Uani 1 1 d . . . H19A H -0.1048 0.1243 0.3688 0.037 Uiso 1 1 calc R . . H19B H -0.1106 0.1960 0.4457 0.037 Uiso 1 1 calc R . . C20 C -0.1302(5) 0.2275(5) 0.3494(5) 0.0365(18) Uani 1 1 d . . . H20A H -0.1067 0.2218 0.2996 0.044 Uiso 1 1 calc R . . H20B H -0.1113 0.2946 0.3766 0.044 Uiso 1 1 calc R . . C21 C -0.2365(6) 0.1750(6) 0.3348(6) 0.054(2) Uani 1 1 d . . . H21A H -0.2556 0.1081 0.3107 0.080 Uiso 1 1 calc R . . H21B H -0.2622 0.1974 0.3006 0.080 Uiso 1 1 calc R . . H21C H -0.2605 0.1857 0.3836 0.080 Uiso 1 1 calc R . . C22 C 0.1375(4) 0.1169(4) 0.3940(4) 0.0197(13) Uani 1 1 d . . . H22A H 0.1273 0.1315 0.4482 0.024 Uiso 1 1 calc R . . H22B H 0.0752 0.0866 0.3613 0.024 Uiso 1 1 calc R . . C23 C 0.1790(4) -0.0025(4) 0.3021(3) 0.0167(12) Uani 1 1 d . . . C24 C 0.1801(4) 0.0481(4) 0.3779(3) 0.0165(12) Uani 1 1 d . . . C25 C 0.2195(4) 0.0351(4) 0.4386(4) 0.0197(13) Uani 1 1 d . . . H25 H 0.2226 0.0708 0.4901 0.024 Uiso 1 1 calc R . . C26 C 0.2541(4) -0.0304(5) 0.4229(4) 0.0224(13) Uani 1 1 d . . . C27 C 0.2524(4) -0.0822(5) 0.3485(4) 0.0238(14) Uani 1 1 d . . . H27 H 0.2765 -0.1271 0.3396 0.029 Uiso 1 1 calc R . . C28 C 0.2156(4) -0.0685(4) 0.2870(4) 0.0205(13) Uani 1 1 d . . . C29 C 0.0430(5) -0.0343(5) 0.2203(4) 0.0254(14) Uani 1 1 d . . . H29A H 0.0132 -0.0444 0.2656 0.030 Uiso 1 1 calc R . . H29B H 0.0241 -0.0960 0.1806 0.030 Uiso 1 1 calc R . . C30 C 0.0105(5) 0.0235(5) 0.1897(4) 0.0303(16) Uani 1 1 d . . . H30A H 0.0306 0.0230 0.1390 0.036 Uiso 1 1 calc R . . H30B H 0.0410 0.0889 0.2248 0.036 Uiso 1 1 calc R . . C31 C -0.0954(6) -0.0115(6) 0.1809(5) 0.0396(19) Uani 1 1 d . . . H31A H -0.1256 -0.0761 0.1443 0.047 Uiso 1 1 calc R . . H31B H -0.1155 -0.0135 0.2311 0.047 Uiso 1 1 calc R . . C32 C -0.1294(7) 0.0476(7) 0.1531(5) 0.057(3) Uani 1 1 d . . . H32A H -0.1031 0.1107 0.1906 0.086 Uiso 1 1 calc R . . H32B H -0.1982 0.0198 0.1468 0.086 Uiso 1 1 calc R . . H32C H -0.1090 0.0507 0.1037 0.086 Uiso 1 1 calc R . . C33 C 0.2158(4) -0.1223(5) 0.2063(4) 0.0238(14) Uani 1 1 d . . . H33A H 0.2598 -0.1502 0.2074 0.029 Uiso 1 1 calc R . . H33B H 0.2405 -0.0781 0.1773 0.029 Uiso 1 1 calc R . . C34 C 0.1063(5) -0.2337(5) 0.0828(4) 0.0230(14) Uani 1 1 d . . . C35 C 0.1201(4) -0.2002(4) 0.1627(4) 0.0200(13) Uani 1 1 d . . . C36 C 0.0479(4) -0.2393(4) 0.2015(4) 0.0191(13) Uani 1 1 d . . . H36 H 0.0569 -0.2175 0.2560 0.023 Uiso 1 1 calc R . . C37 C -0.0375(5) -0.3106(4) 0.1599(4) 0.0219(13) Uani 1 1 d . . . C38 C -0.0512(4) -0.3449(4) 0.0811(4) 0.0214(13) Uani 1 1 d . . . H38 H -0.1099 -0.3947 0.0539 0.026 Uiso 1 1 calc R . . C39 C 0.0213(5) -0.3066(4) 0.0406(4) 0.0215(13) Uani 1 1 d . . . C40 C 0.1794(5) -0.1208(5) 0.0224(4) 0.0224(13) Uani 1 1 d . . . H40A H 0.1810 -0.0700 0.0676 0.027 Uiso 1 1 calc R . . H40B H 0.1212 -0.1441 -0.0140 0.027 Uiso 1 1 calc R . . C41 C 0.2650(5) -0.0845(5) -0.0158(4) 0.0266(15) Uani 1 1 d . . . H41A H 0.3221 -0.0635 0.0210 0.032 Uiso 1 1 calc R . . H41B H 0.2682 -0.0294 -0.0279 0.032 Uiso 1 1 calc R . . C42 C 0.2654(5) -0.1562(5) -0.0892(5) 0.0341(17) Uani 1 1 d . . . H42A H 0.2067 -0.1801 -0.1251 0.041 Uiso 1 1 calc R . . H42B H 0.2667 -0.2095 -0.0769 0.041 Uiso 1 1 calc R . . C43 C 0.3500(6) -0.1146(6) -0.1282(5) 0.045(2) Uani 1 1 d . . . H43A H 0.3473 -0.0636 -0.1427 0.067 Uiso 1 1 calc R . . H43B H 0.3487 -0.1631 -0.1743 0.067 Uiso 1 1 calc R . . H43C H 0.4082 -0.0903 -0.0926 0.067 Uiso 1 1 calc R . . C44 C 0.0068(5) -0.3451(5) -0.0460(4) 0.0236(14) Uani 1 1 d . . . H44A H -0.0257 -0.4142 -0.0619 0.028 Uiso 1 1 calc R . . H44B H 0.0693 -0.3276 -0.0626 0.028 Uiso 1 1 calc R . . C45 C 0.4008(4) 0.1466(4) -0.1743(4) 0.0189(13) Uani 1 1 d . . . C46 C 0.3420(5) 0.1657(4) -0.2166(4) 0.0223(13) Uani 1 1 d . . . C47 C 0.3071(5) 0.2285(5) -0.1772(4) 0.0258(14) Uani 1 1 d . . . H47 H 0.2660 0.2422 -0.2039 0.031 Uiso 1 1 calc R . . C48 C 0.3342(5) 0.2695(5) -0.0991(4) 0.0274(15) Uani 1 1 d . . . C49 C 0.3942(5) 0.2529(5) -0.0570(4) 0.0231(14) Uani 1 1 d . . . H49 H 0.4117 0.2835 -0.0031 0.028 Uiso 1 1 calc R . . C50 C 0.4287(5) 0.1897(5) -0.0957(4) 0.0233(14) Uani 1 1 d . . . C51 C 0.5112(5) 0.1080(5) -0.2460(4) 0.0325(17) Uani 1 1 d . . . H51A H 0.5667 0.1285 -0.2077 0.039 Uiso 1 1 calc R . . H51B H 0.5182 0.1615 -0.2626 0.039 Uiso 1 1 calc R . . C52 C 0.5040(5) 0.0268(5) -0.3147(4) 0.0324(17) Uani 1 1 d . . . H52A H 0.4442 0.0024 -0.3494 0.039 Uiso 1 1 calc R . . H52B H 0.5563 0.0498 -0.3434 0.039 Uiso 1 1 calc R . . C53 C 0.5075(5) -0.0513(5) -0.2925(5) 0.0357(18) Uani 1 1 d . . . H53A H 0.4551 -0.0750 -0.2641 0.043 Uiso 1 1 calc R . . H53B H 0.5673 -0.0275 -0.2579 0.043 Uiso 1 1 calc R . . C54 C 0.5002(7) -0.1326(6) -0.3643(5) 0.047(2) Uani 1 1 d . . . H54A H 0.4423 -0.1545 -0.3995 0.071 Uiso 1 1 calc R . . H54B H 0.4989 -0.1841 -0.3483 0.071 Uiso 1 1 calc R . . H54C H 0.5546 -0.1104 -0.3902 0.071 Uiso 1 1 calc R . . C55 C 0.4946(5) 0.1663(5) -0.0533(4) 0.0244(14) Uani 1 1 d . . . H55A H 0.4696 0.0975 -0.0692 0.029 Uiso 1 1 calc R . . H55B H 0.5569 0.1908 -0.0700 0.029 Uiso 1 1 calc R . . C56 C 0.5928(4) 0.2771(4) 0.0770(4) 0.0189(13) Uani 1 1 d . . . C57 C 0.5082(5) 0.2046(4) 0.0332(4) 0.0232(14) Uani 1 1 d . . . C58 C 0.4344(4) 0.1679(4) 0.0728(4) 0.0236(14) Uani 1 1 d . . . H58 H 0.3751 0.1199 0.0449 0.028 Uiso 1 1 calc R . . C59 C 0.4472(5) 0.2008(5) 0.1515(4) 0.0245(14) Uani 1 1 d . . . C60 C 0.5327(4) 0.2704(4) 0.1950(4) 0.0223(13) Uani 1 1 d . . . H60 H 0.5404 0.2910 0.2495 0.027 Uiso 1 1 calc R . . C61 C 0.6069(4) 0.3094(4) 0.1571(4) 0.0203(13) Uani 1 1 d . . . C62 C 0.6685(5) 0.3895(5) 0.0165(4) 0.0252(14) Uani 1 1 d . . . H62A H 0.6771 0.4429 0.0623 0.030 Uiso 1 1 calc R . . H62B H 0.6078 0.3687 -0.0155 0.030 Uiso 1 1 calc R . . C63 C 0.7474(5) 0.4186(5) -0.0283(4) 0.0281(15) Uani 1 1 d . . . H63A H 0.8069 0.4356 0.0036 0.034 Uiso 1 1 calc R . . H63B H 0.7526 0.4753 -0.0388 0.034 Uiso 1 1 calc R . . C64 C 0.7360(5) 0.3442(5) -0.1043(4) 0.0314(16) Uani 1 1 d . . . H64A H 0.6758 0.3257 -0.1360 0.038 Uiso 1 1 calc R . . H64B H 0.7333 0.2882 -0.0940 0.038 Uiso 1 1 calc R . . C65 C 0.8169(7) 0.3784(6) -0.1494(6) 0.049(2) Uani 1 1 d . . . H65A H 0.8195 0.4334 -0.1602 0.073 Uiso 1 1 calc R . . H65B H 0.8064 0.3287 -0.1978 0.073 Uiso 1 1 calc R . . H65C H 0.8765 0.3950 -0.1189 0.073 Uiso 1 1 calc R . . C66 C 0.7041(4) 0.3805(4) 0.2007(4) 0.0231(14) Uani 1 1 d . . . H66A H 0.7447 0.3482 0.1975 0.028 Uiso 1 1 calc R . . H66B H 0.7311 0.4276 0.1746 0.028 Uiso 1 1 calc R . . C67 C 0.6763(4) 0.5007(4) 0.3047(4) 0.0211(13) Uani 1 1 d . . . C68 C 0.7077(4) 0.4308(4) 0.2844(4) 0.0198(13) Uani 1 1 d . . . C69 C 0.7434(5) 0.4106(5) 0.3424(4) 0.0268(15) Uani 1 1 d . . . H69 H 0.7646 0.3634 0.3296 0.032 Uiso 1 1 calc R . . C70 C 0.7483(5) 0.4583(5) 0.4181(4) 0.0295(15) Uani 1 1 d . . . C71 C 0.7167(4) 0.5267(4) 0.4389(4) 0.0228(14) Uani 1 1 d . . . H71 H 0.7203 0.5587 0.4916 0.027 Uiso 1 1 calc R . . C72 C 0.6796(4) 0.5484(4) 0.3822(4) 0.0215(13) Uani 1 1 d . . . C73 C 0.5539(6) 0.5115(7) 0.2334(5) 0.046(2) Uani 1 1 d . . . H73A H 0.5489 0.5662 0.2691 0.055 Uiso 1 1 calc R . . H73B H 0.5098 0.4549 0.2440 0.055 Uiso 1 1 calc R . . C74 C 0.5282(7) 0.5034(8) 0.1544(6) 0.057(3) Uani 1 1 d . . . H74A H 0.5119 0.4387 0.1212 0.069 Uiso 1 1 calc R . . H74B H 0.5844 0.5456 0.1384 0.069 Uiso 1 1 calc R . . C75 C 0.4486(7) 0.5253(7) 0.1393(6) 0.054(2) Uani 1 1 d . . . H75A H 0.4332 0.5100 0.0832 0.065 Uiso 1 1 calc R . . H75B H 0.4695 0.5933 0.1634 0.065 Uiso 1 1 calc R . . C76 C 0.3601(7) 0.4735(9) 0.1688(5) 0.062(3) Uani 1 1 d . . . H76A H 0.3379 0.4061 0.1445 0.093 Uiso 1 1 calc R . . H76B H 0.3114 0.4911 0.1563 0.093 Uiso 1 1 calc R . . H76C H 0.3738 0.4899 0.2245 0.093 Uiso 1 1 calc R . . C77 C 0.6458(4) 0.6232(4) 0.4064(3) 0.0180(12) Uani 1 1 d . . . H77A H 0.6428 0.6387 0.4620 0.022 Uiso 1 1 calc R . . H77B H 0.5814 0.5984 0.3788 0.022 Uiso 1 1 calc R . . C78 C 0.6728(4) 0.7620(4) 0.3625(3) 0.0204(13) Uani 1 1 d . . . C79 C 0.7092(4) 0.7117(4) 0.3900(3) 0.0171(12) Uani 1 1 d . . . C80 C 0.8067(4) 0.7453(4) 0.4033(3) 0.0180(12) Uani 1 1 d . . . H80 H 0.8335 0.7128 0.4226 0.022 Uiso 1 1 calc R . . C81 C 0.8647(4) 0.8262(4) 0.3886(4) 0.0216(13) Uani 1 1 d . . . C82 C 0.8278(5) 0.8736(4) 0.3579(4) 0.0233(14) Uani 1 1 d . . . H82 H 0.8684 0.9281 0.3471 0.028 Uiso 1 1 calc R . . C83 C 0.7303(5) 0.8401(4) 0.3430(3) 0.0204(13) Uani 1 1 d . . . C84 C 0.5402(5) 0.7557(6) 0.4235(4) 0.0337(18) Uani 1 1 d . . . H84A H 0.5453 0.7185 0.4548 0.040 Uiso 1 1 calc R A 1 H84B H 0.5785 0.8227 0.4530 0.040 Uiso 1 1 calc R A 1 C85A C 0.442(2) 0.737(2) 0.4075(18) 0.111(10) Uiso 0.548(19) 1 d P B 1 H85A H 0.4182 0.7358 0.4565 0.133 Uiso 0.548(19) 1 calc PR B 1 H85B H 0.4451 0.7946 0.4000 0.133 Uiso 0.548(19) 1 calc PR B 1 C86A C 0.3728(9) 0.6671(9) 0.3535(7) 0.026(3) Uiso 0.548(19) 1 d P B 1 H86A H 0.3526 0.6080 0.3649 0.031 Uiso 0.548(19) 1 calc PR B 1 H86B H 0.3930 0.6586 0.3024 0.031 Uiso 0.548(19) 1 calc PR B 1 C85B C 0.4338(11) 0.6754(12) 0.4092(10) 0.031(5) Uiso 0.452(19) 1 d P B 2 H85C H 0.4099 0.6701 0.4577 0.037 Uiso 0.452(19) 1 calc PR B 2 H85D H 0.4263 0.6138 0.3754 0.037 Uiso 0.452(19) 1 calc PR B 2 C86B C 0.3797(18) 0.7302(18) 0.3600(14) 0.060(7) Uiso 0.452(19) 1 d P B 2 H86C H 0.4065 0.7980 0.3886 0.072 Uiso 0.452(19) 1 calc PR B 2 H86D H 0.3960 0.7224 0.3076 0.072 Uiso 0.452(19) 1 calc PR B 2 C87 C 0.2946(18) 0.696(2) 0.3559(13) 0.207(14) Uani 1 1 d . . . H87A H 0.2380 0.6442 0.3221 0.311 Uiso 1 1 calc R B 1 H87B H 0.3134 0.7503 0.3387 0.311 Uiso 1 1 calc R B 1 H87C H 0.2814 0.7121 0.4086 0.311 Uiso 1 1 calc R B 1 C88 C 0.6873(5) 0.8850(5) 0.3029(4) 0.0242(14) Uani 1 1 d . . . H88A H 0.7335 0.9506 0.3121 0.029 Uiso 1 1 calc R . . H88B H 0.6315 0.8859 0.3258 0.029 Uiso 1 1 calc R . . O1 O 0.0623(3) 0.4298(3) 0.2068(2) 0.0207(9) Uani 1 1 d . . . O2 O 0.0577(3) 0.2197(3) 0.3421(2) 0.0205(9) Uani 1 1 d . . . O3 O 0.1445(3) 0.0132(3) 0.2416(3) 0.0229(10) Uani 1 1 d . . . O4 O 0.1806(3) -0.1958(3) 0.0460(2) 0.0217(9) Uani 1 1 d . . . O5 O 0.4263(3) 0.0766(3) -0.2129(2) 0.0200(9) Uani 1 1 d . . . O6 O 0.6682(3) 0.3140(3) 0.0399(2) 0.0213(9) Uani 1 1 d . . . O7 O 0.6483(3) 0.5224(3) 0.2459(3) 0.0270(10) Uani 1 1 d . . . O8 O 0.5757(3) 0.7316(3) 0.3517(3) 0.0257(10) Uani 1 1 d . B . Br1 Br 0.16101(6) 0.12216(5) 0.03433(4) 0.03351(18) Uani 1 1 d . . . Br2 Br 0.48055(4) 0.38362(5) 0.40106(4) 0.02750(16) Uani 1 1 d . . . Br3 Br 0.30829(6) -0.04864(6) 0.50631(4) 0.03783(19) Uani 1 1 d . . . Br4 Br -0.13972(5) -0.35932(5) 0.21236(4) 0.02623(16) Uani 1 1 d . . . Br5 Br 0.28064(6) 0.34840(6) -0.04387(4) 0.03672(19) Uani 1 1 d . . . Br6 Br 0.34392(5) 0.14784(5) 0.20230(4) 0.02772(16) Uani 1 1 d . . . Br7 Br 0.80104(7) 0.43285(7) 0.49713(5) 0.0473(2) Uani 1 1 d . . . Br8 Br 0.99664(4) 0.87496(5) 0.41291(4) 0.02546(16) 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 0.023(3) 0.016(3) 0.014(3) 0.001(2) 0.003(2) 0.008(3) C2 0.025(3) 0.022(3) 0.018(3) 0.007(3) 0.005(3) 0.010(3) C3 0.030(4) 0.026(3) 0.012(3) 0.001(3) 0.006(3) 0.013(3) C4 0.034(4) 0.022(3) 0.022(3) 0.004(3) 0.010(3) 0.016(3) C5 0.030(4) 0.020(3) 0.022(3) 0.006(3) 0.002(3) 0.015(3) C6 0.023(3) 0.017(3) 0.017(3) 0.001(2) 0.005(2) 0.006(3) C7 0.031(4) 0.035(4) 0.036(4) 0.013(3) 0.015(3) 0.017(3) C8 0.037(4) 0.054(5) 0.046(5) 0.015(4) 0.010(4) 0.028(4) C9 0.095(9) 0.113(10) 0.044(6) -0.021(6) -0.024(6) 0.078(8) C10 0.131(12) 0.115(11) 0.084(9) -0.054(8) -0.021(8) 0.098(11) C11 0.041(4) 0.020(3) 0.018(3) 0.006(3) 0.002(3) 0.016(3) C12 0.021(3) 0.023(3) 0.012(3) 0.004(2) 0.002(2) 0.012(3) C13 0.024(3) 0.020(3) 0.016(3) 0.001(2) 0.004(2) 0.009(3) C14 0.026(3) 0.015(3) 0.017(3) 0.006(2) 0.008(3) 0.004(3) C15 0.017(3) 0.015(3) 0.018(3) 0.001(2) 0.006(2) 0.000(2) C16 0.018(3) 0.021(3) 0.013(3) 0.005(2) 0.007(2) 0.008(3) C17 0.017(3) 0.012(3) 0.016(3) 0.004(2) 0.008(2) 0.001(2) C18 0.030(4) 0.040(4) 0.022(3) 0.007(3) 0.007(3) 0.019(3) C19 0.028(4) 0.030(4) 0.032(4) 0.011(3) 0.014(3) 0.009(3) C20 0.026(4) 0.028(4) 0.048(5) 0.008(3) 0.000(3) 0.008(3) C21 0.031(4) 0.041(5) 0.083(7) 0.021(5) -0.001(5) 0.012(4) C22 0.017(3) 0.020(3) 0.021(3) 0.007(3) 0.004(2) 0.007(3) C23 0.010(3) 0.016(3) 0.014(3) 0.002(2) 0.002(2) -0.001(2) C24 0.010(3) 0.016(3) 0.022(3) 0.009(2) 0.003(2) 0.003(2) C25 0.016(3) 0.022(3) 0.018(3) 0.004(2) 0.002(2) 0.007(3) C26 0.016(3) 0.028(3) 0.022(3) 0.011(3) -0.003(2) 0.008(3) C27 0.019(3) 0.025(3) 0.030(4) 0.010(3) 0.005(3) 0.012(3) C28 0.013(3) 0.018(3) 0.021(3) 0.003(2) 0.002(2) 0.001(2) C29 0.021(3) 0.026(3) 0.030(4) 0.011(3) -0.001(3) 0.010(3) C30 0.039(4) 0.028(4) 0.021(3) 0.004(3) -0.003(3) 0.014(3) C31 0.037(4) 0.060(5) 0.032(4) 0.017(4) 0.005(3) 0.031(4) C32 0.063(6) 0.077(7) 0.040(5) 0.001(5) -0.008(4) 0.051(6) C33 0.018(3) 0.025(3) 0.022(3) 0.005(3) 0.003(3) 0.006(3) C34 0.022(3) 0.029(3) 0.024(3) 0.011(3) 0.005(3) 0.015(3) C35 0.015(3) 0.021(3) 0.022(3) 0.003(3) 0.002(2) 0.008(3) C36 0.023(3) 0.018(3) 0.016(3) 0.005(2) 0.003(2) 0.010(3) C37 0.023(3) 0.018(3) 0.026(3) 0.006(3) 0.006(3) 0.012(3) C38 0.015(3) 0.019(3) 0.024(3) 0.002(3) 0.001(2) 0.005(3) C39 0.028(3) 0.024(3) 0.017(3) 0.006(3) 0.000(3) 0.017(3) C40 0.025(3) 0.026(3) 0.020(3) 0.007(3) 0.005(3) 0.014(3) C41 0.024(3) 0.029(4) 0.031(4) 0.015(3) 0.006(3) 0.012(3) C42 0.037(4) 0.034(4) 0.040(4) 0.016(3) 0.018(3) 0.022(4) C43 0.052(5) 0.051(5) 0.063(6) 0.042(5) 0.037(5) 0.036(4) C44 0.029(4) 0.028(3) 0.017(3) 0.003(3) 0.000(3) 0.018(3) C45 0.021(3) 0.015(3) 0.021(3) 0.007(2) 0.006(2) 0.008(3) C46 0.031(4) 0.022(3) 0.018(3) 0.007(3) 0.003(3) 0.015(3) C47 0.034(4) 0.029(4) 0.025(3) 0.010(3) 0.003(3) 0.023(3) C48 0.036(4) 0.027(4) 0.024(4) 0.004(3) 0.005(3) 0.023(3) C49 0.031(4) 0.025(3) 0.017(3) 0.004(3) 0.000(3) 0.018(3) C50 0.022(3) 0.025(3) 0.020(3) 0.006(3) 0.004(3) 0.009(3) C51 0.020(3) 0.032(4) 0.038(4) 0.002(3) 0.009(3) 0.010(3) C52 0.031(4) 0.039(4) 0.033(4) 0.010(3) 0.015(3) 0.022(3) C53 0.024(4) 0.040(4) 0.047(5) 0.017(4) 0.007(3) 0.017(3) C54 0.050(5) 0.039(5) 0.055(6) 0.008(4) 0.011(4) 0.027(4) C55 0.026(3) 0.028(4) 0.023(3) 0.005(3) 0.000(3) 0.018(3) C56 0.016(3) 0.023(3) 0.023(3) 0.011(3) 0.007(2) 0.011(3) C57 0.027(3) 0.022(3) 0.023(3) 0.005(3) 0.002(3) 0.015(3) C58 0.017(3) 0.021(3) 0.025(3) 0.000(3) -0.004(3) 0.006(3) C59 0.020(3) 0.026(3) 0.026(4) 0.005(3) 0.008(3) 0.011(3) C60 0.019(3) 0.023(3) 0.026(3) 0.008(3) 0.002(3) 0.010(3) C61 0.013(3) 0.018(3) 0.021(3) 0.000(2) 0.001(2) 0.002(2) C62 0.032(4) 0.022(3) 0.026(3) 0.005(3) 0.007(3) 0.018(3) C63 0.026(4) 0.017(3) 0.036(4) 0.008(3) 0.002(3) 0.005(3) C64 0.039(4) 0.025(4) 0.038(4) 0.013(3) 0.020(3) 0.019(3) C65 0.061(6) 0.043(5) 0.069(6) 0.040(5) 0.045(5) 0.034(5) C66 0.019(3) 0.022(3) 0.021(3) 0.004(3) 0.002(3) 0.005(3) C67 0.014(3) 0.021(3) 0.018(3) 0.008(3) 0.004(2) -0.002(2) C68 0.014(3) 0.014(3) 0.020(3) 0.002(2) 0.006(2) -0.002(2) C69 0.026(4) 0.028(4) 0.026(4) 0.003(3) 0.005(3) 0.016(3) C70 0.029(4) 0.034(4) 0.026(4) 0.013(3) 0.000(3) 0.012(3) C71 0.018(3) 0.021(3) 0.021(3) 0.002(3) -0.002(2) 0.005(3) C72 0.013(3) 0.021(3) 0.024(3) 0.006(3) 0.003(2) 0.003(3) C73 0.028(4) 0.076(6) 0.044(5) 0.026(5) 0.002(4) 0.027(4) C74 0.040(5) 0.080(7) 0.062(6) 0.039(6) 0.010(4) 0.025(5) C75 0.050(6) 0.072(7) 0.048(6) 0.027(5) 0.003(4) 0.029(5) C76 0.043(5) 0.108(9) 0.042(5) 0.040(6) 0.010(4) 0.030(6) C77 0.014(3) 0.021(3) 0.018(3) 0.007(2) 0.010(2) 0.005(2) C78 0.017(3) 0.023(3) 0.016(3) 0.001(2) 0.003(2) 0.008(3) C79 0.014(3) 0.018(3) 0.013(3) 0.003(2) 0.003(2) 0.003(2) C80 0.020(3) 0.021(3) 0.018(3) 0.009(2) 0.002(2) 0.012(3) C81 0.019(3) 0.020(3) 0.017(3) 0.003(2) 0.005(2) 0.003(3) C82 0.022(3) 0.021(3) 0.018(3) 0.006(3) 0.008(3) 0.001(3) C83 0.031(3) 0.021(3) 0.009(3) 0.000(2) 0.000(2) 0.015(3) C84 0.022(3) 0.056(5) 0.025(4) 0.005(3) 0.005(3) 0.024(4) C87 0.28(3) 0.40(4) 0.22(2) 0.24(3) 0.17(2) 0.31(3) C88 0.031(4) 0.026(3) 0.019(3) 0.005(3) -0.001(3) 0.017(3) O1 0.021(2) 0.018(2) 0.020(2) 0.0029(18) 0.0049(18) 0.0078(19) O2 0.016(2) 0.029(2) 0.016(2) 0.0034(18) 0.0021(17) 0.0126(19) O3 0.014(2) 0.029(2) 0.024(2) 0.0119(19) 0.0001(17) 0.0050(19) O4 0.027(2) 0.025(2) 0.019(2) 0.0098(18) 0.0097(18) 0.015(2) O5 0.019(2) 0.019(2) 0.020(2) 0.0015(17) 0.0052(17) 0.0093(18) O6 0.025(2) 0.023(2) 0.018(2) 0.0067(18) 0.0056(18) 0.012(2) O7 0.027(3) 0.035(3) 0.019(2) 0.010(2) 0.0013(19) 0.013(2) O8 0.020(2) 0.034(3) 0.021(2) 0.004(2) -0.0020(18) 0.014(2) Br1 0.0488(5) 0.0376(4) 0.0235(4) 0.0038(3) 0.0051(3) 0.0320(4) Br2 0.0166(3) 0.0249(3) 0.0297(4) 0.0053(3) 0.0066(3) 0.0012(3) Br3 0.0464(5) 0.0476(5) 0.0258(4) 0.0117(3) -0.0048(3) 0.0272(4) Br4 0.0202(3) 0.0261(3) 0.0305(4) 0.0115(3) 0.0059(3) 0.0069(3) Br5 0.0526(5) 0.0488(5) 0.0263(4) 0.0090(3) 0.0101(3) 0.0407(4) Br6 0.0200(3) 0.0303(4) 0.0266(3) 0.0082(3) 0.0046(3) 0.0062(3) Br7 0.0650(6) 0.0673(6) 0.0304(4) 0.0203(4) 0.0042(4) 0.0456(5) Br8 0.0141(3) 0.0283(3) 0.0272(3) 0.0094(3) 0.0043(2) 0.0029(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 O1 1.384(7) . ? C1 C6 1.390(9) . ? C1 C2 1.405(8) . ? C2 C3 1.400(9) . ? C2 C44 1.522(9) 2 ? C3 C4 1.369(10) . ? C3 H3 0.9500 . ? C4 C5 1.385(9) . ? C4 Br1 1.902(6) . ? C5 C6 1.403(9) . ? C5 H5 0.9500 . ? C6 C11 1.531(9) . ? C7 O1 1.446(8) . ? C7 C8 1.527(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.465(12) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.546(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C13 1.512(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O2 1.383(7) . ? C12 C13 1.400(9) . ? C12 C17 1.402(9) . ? C13 C14 1.393(9) . ? C14 C15 1.387(9) . ? C14 H14 0.9500 . ? C15 C16 1.376(9) . ? C15 Br2 1.907(6) . ? C16 C17 1.385(8) . ? C16 H16 0.9500 . ? C17 C22 1.522(8) . ? C18 O2 1.453(8) . ? C18 C19 1.542(10) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.504(11) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.514(11) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C24 1.522(8) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O3 1.374(7) . ? C23 C24 1.402(8) . ? C23 C28 1.408(9) . ? C24 C25 1.389(9) . ? C25 C26 1.378(9) . ? C25 H25 0.9500 . ? C26 C27 1.385(9) . ? C26 Br3 1.912(6) . ? C27 C28 1.390(9) . ? C27 H27 0.9500 . ? C28 C33 1.498(9) . ? C29 O3 1.450(7) . ? C29 C30 1.497(9) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.517(10) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.505(12) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C35 1.529(8) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 O4 1.378(8) . ? C34 C35 1.394(9) . ? C34 C39 1.395(9) . ? C35 C36 1.386(9) . ? C36 C37 1.388(9) . ? C36 H36 0.9500 . ? C37 C38 1.374(9) . ? C37 Br4 1.904(6) . ? C38 C39 1.407(9) . ? C38 H38 0.9500 . ? C39 C44 1.510(9) . ? C40 O4 1.448(8) . ? C40 C41 1.515(9) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.523(10) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.531(10) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 C2 1.522(9) 2 ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C50 1.386(9) . ? C45 O5 1.396(7) . ? C45 C46 1.398(9) . ? C46 C47 1.408(9) . ? C46 C88 1.526(9) 2_665 ? C47 C48 1.373(9) . ? C47 H47 0.9500 . ? C48 C49 1.383(9) . ? C48 Br5 1.915(6) . ? C49 C50 1.404(9) . ? C49 H49 0.9500 . ? C50 C55 1.533(9) . ? C51 O5 1.443(8) . ? C51 C52 1.521(10) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 C53 1.499(11) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.554(11) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 C57 1.511(9) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 O6 1.391(7) . ? C56 C61 1.394(9) . ? C56 C57 1.398(9) . ? C57 C58 1.402(9) . ? C58 C59 1.372(9) . ? C58 H58 0.9500 . ? C59 C60 1.391(9) . ? C59 Br6 1.912(6) . ? C60 C61 1.396(9) . ? C60 H60 0.9500 . ? C61 C66 1.517(8) . ? C62 O6 1.444(8) . ? C62 C63 1.496(9) . ? C62 H62A 0.9900 . ? C62 H62B 0.9900 . ? C63 C64 1.525(10) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 C65 1.537(10) . ? C64 H64A 0.9900 . ? C64 H64B 0.9900 . ? C65 H65A 0.9800 . ? C65 H65B 0.9800 . ? C65 H65C 0.9800 . ? C66 C68 1.514(8) . ? C66 H66A 0.9900 . ? C66 H66B 0.9900 . ? C67 O7 1.362(8) . ? C67 C72 1.406(9) . ? C67 C68 1.409(9) . ? C68 C69 1.391(10) . ? C69 C70 1.372(10) . ? C69 H69 0.9500 . ? C70 C71 1.388(10) . ? C70 Br7 1.906(7) . ? C71 C72 1.398(9) . ? C71 H71 0.9500 . ? C72 C77 1.511(9) . ? C73 O7 1.437(9) . ? C73 C74 1.459(12) . ? C73 H73A 0.9900 . ? C73 H73B 0.9900 . ? C74 C75 1.497(13) . ? C74 H74A 0.9900 . ? C74 H74B 0.9900 . ? C75 C76 1.514(13) . ? C75 H75A 0.9900 . ? C75 H75B 0.9900 . ? C76 H76A 0.9800 . ? C76 H76B 0.9800 . ? C76 H76C 0.9800 . ? C77 C79 1.521(8) . ? C77 H77A 0.9900 . ? C77 H77B 0.9900 . ? C78 C79 1.393(9) . ? C78 O8 1.395(7) . ? C78 C83 1.398(9) . ? C79 C80 1.395(8) . ? C80 C81 1.389(9) . ? C80 H80 0.9500 . ? C81 C82 1.389(10) . ? C81 Br8 1.890(6) . ? C82 C83 1.396(9) . ? C82 H82 0.9500 . ? C83 C88 1.520(9) . ? C84 C85A 1.46(3) . ? C84 O8 1.459(8) . ? C84 C85B 1.612(18) . ? C84 H84A 0.9900 . ? C84 H84B 0.9900 . ? C85A C86A 1.33(3) . ? C85A H85A 0.9900 . ? C85A H85B 0.9900 . ? C86A C87 1.503(19) . ? C86A H86A 0.9900 . ? C86A H86B 0.9900 . ? C85B C86B 1.87(3) . ? C85B H85C 0.9900 . ? C85B H85D 0.9900 . ? C86B C87 1.22(3) . ? C86B H86C 0.9900 . ? C86B H86D 0.9900 . ? C87 H87A 0.9800 . ? C87 H87B 0.9800 . ? C87 H87C 0.9800 . ? C88 C46 1.526(9) 2_665 ? C88 H88A 0.9900 . ? C88 H88B 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 C6 118.2(5) . . ? O1 C1 C2 119.6(6) . . ? C6 C1 C2 122.0(6) . . ? C3 C2 C1 117.9(6) . . ? C3 C2 C44 122.0(6) . 2 ? C1 C2 C44 120.1(6) . 2 ? C4 C3 C2 119.9(6) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 122.6(6) . . ? C3 C4 Br1 118.3(5) . . ? C5 C4 Br1 119.1(5) . . ? C4 C5 C6 118.7(6) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C1 C6 C5 118.9(6) . . ? C1 C6 C11 119.0(5) . . ? C5 C6 C11 122.1(6) . . ? O1 C7 C8 107.0(6) . . ? O1 C7 H7A 110.3 . . ? C8 C7 H7A 110.3 . . ? O1 C7 H7B 110.3 . . ? C8 C7 H7B 110.3 . . ? H7A C7 H7B 108.6 . . ? C9 C8 C7 112.7(8) . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C8 C9 C10 111.2(10) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C11 C6 113.6(5) . . ? C13 C11 H11A 108.8 . . ? C6 C11 H11A 108.8 . . ? C13 C11 H11B 108.8 . . ? C6 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? O2 C12 C13 118.1(6) . . ? O2 C12 C17 120.4(5) . . ? C13 C12 C17 121.5(6) . . ? C14 C13 C12 118.3(6) . . ? C14 C13 C11 120.6(6) . . ? C12 C13 C11 121.0(6) . . ? C15 C14 C13 119.3(6) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C16 C15 C14 122.3(6) . . ? C16 C15 Br2 119.0(5) . . ? C14 C15 Br2 118.7(5) . . ? C15 C16 C17 119.4(6) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C16 C17 C12 118.8(6) . . ? C16 C17 C22 121.2(6) . . ? C12 C17 C22 119.9(5) . . ? O2 C18 C19 107.7(5) . . ? O2 C18 H18A 110.2 . . ? C19 C18 H18A 110.2 . . ? O2 C18 H18B 110.2 . . ? C19 C18 H18B 110.2 . . ? H18A C18 H18B 108.5 . . ? C20 C19 C18 114.0(6) . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 112.2(7) . . ? C19 C20 H20A 109.2 . . ? C21 C20 H20A 109.2 . . ? C19 C20 H20B 109.2 . . ? C21 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C24 C22 C17 113.9(5) . . ? C24 C22 H22A 108.8 . . ? C17 C22 H22A 108.8 . . ? C24 C22 H22B 108.8 . . ? C17 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? O3 C23 C24 120.5(6) . . ? O3 C23 C28 119.2(5) . . ? C24 C23 C28 120.3(6) . . ? C25 C24 C23 120.0(6) . . ? C25 C24 C22 119.8(5) . . ? C23 C24 C22 120.2(6) . . ? C26 C25 C24 119.0(6) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C25 C26 C27 122.0(6) . . ? C25 C26 Br3 119.1(5) . . ? C27 C26 Br3 118.9(5) . . ? C26 C27 C28 119.9(6) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C27 C28 C23 118.8(6) . . ? C27 C28 C33 120.3(6) . . ? C23 C28 C33 120.9(6) . . ? O3 C29 C30 109.6(5) . . ? O3 C29 H29A 109.7 . . ? C30 C29 H29A 109.7 . . ? O3 C29 H29B 109.7 . . ? C30 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? C29 C30 C31 112.7(6) . . ? C29 C30 H30A 109.0 . . ? C31 C30 H30A 109.0 . . ? C29 C30 H30B 109.0 . . ? C31 C30 H30B 109.0 . . ? H30A C30 H30B 107.8 . . ? C32 C31 C30 113.7(8) . . ? C32 C31 H31A 108.8 . . ? C30 C31 H31A 108.8 . . ? C32 C31 H31B 108.8 . . ? C30 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C28 C33 C35 115.3(5) . . ? C28 C33 H33A 108.5 . . ? C35 C33 H33A 108.5 . . ? C28 C33 H33B 108.5 . . ? C35 C33 H33B 108.5 . . ? H33A C33 H33B 107.5 . . ? O4 C34 C35 118.3(6) . . ? O4 C34 C39 120.3(6) . . ? C35 C34 C39 121.3(6) . . ? C36 C35 C34 119.7(6) . . ? C36 C35 C33 121.1(6) . . ? C34 C35 C33 119.2(6) . . ? C35 C36 C37 119.4(6) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C38 C37 C36 121.3(6) . . ? C38 C37 Br4 119.0(5) . . ? C36 C37 Br4 119.7(5) . . ? C37 C38 C39 120.3(6) . . ? C37 C38 H38 119.8 . . ? C39 C38 H38 119.8 . . ? C34 C39 C38 118.0(6) . . ? C34 C39 C44 121.6(6) . . ? C38 C39 C44 120.4(6) . . ? O4 C40 C41 108.0(5) . . ? O4 C40 H40A 110.1 . . ? C41 C40 H40A 110.1 . . ? O4 C40 H40B 110.1 . . ? C41 C40 H40B 110.1 . . ? H40A C40 H40B 108.4 . . ? C40 C41 C42 113.9(6) . . ? C40 C41 H41A 108.8 . . ? C42 C41 H41A 108.8 . . ? C40 C41 H41B 108.8 . . ? C42 C41 H41B 108.8 . . ? H41A C41 H41B 107.7 . . ? C41 C42 C43 112.0(7) . . ? C41 C42 H42A 109.2 . . ? C43 C42 H42A 109.2 . . ? C41 C42 H42B 109.2 . . ? C43 C42 H42B 109.2 . . ? H42A C42 H42B 107.9 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C39 C44 C2 115.6(5) . 2 ? C39 C44 H44A 108.4 . . ? C2 C44 H44A 108.4 2 . ? C39 C44 H44B 108.4 . . ? C2 C44 H44B 108.4 2 . ? H44A C44 H44B 107.4 . . ? C50 C45 O5 119.6(6) . . ? C50 C45 C46 122.5(6) . . ? O5 C45 C46 117.7(5) . . ? C45 C46 C47 118.5(6) . . ? C45 C46 C88 120.0(6) . 2_665 ? C47 C46 C88 121.4(6) . 2_665 ? C48 C47 C46 118.2(6) . . ? C48 C47 H47 120.9 . . ? C46 C47 H47 120.9 . . ? C47 C48 C49 123.7(6) . . ? C47 C48 Br5 118.6(5) . . ? C49 C48 Br5 117.6(5) . . ? C48 C49 C50 118.5(6) . . ? C48 C49 H49 120.8 . . ? C50 C49 H49 120.8 . . ? C45 C50 C49 118.5(6) . . ? C45 C50 C55 119.6(6) . . ? C49 C50 C55 121.9(6) . . ? O5 C51 C52 107.9(6) . . ? O5 C51 H51A 110.1 . . ? C52 C51 H51A 110.1 . . ? O5 C51 H51B 110.1 . . ? C52 C51 H51B 110.1 . . ? H51A C51 H51B 108.4 . . ? C53 C52 C51 113.0(7) . . ? C53 C52 H52A 109.0 . . ? C51 C52 H52A 109.0 . . ? C53 C52 H52B 109.0 . . ? C51 C52 H52B 109.0 . . ? H52A C52 H52B 107.8 . . ? C52 C53 C54 111.2(7) . . ? C52 C53 H53A 109.4 . . ? C54 C53 H53A 109.4 . . ? C52 C53 H53B 109.4 . . ? C54 C53 H53B 109.4 . . ? H53A C53 H53B 108.0 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C57 C55 C50 115.3(5) . . ? C57 C55 H55A 108.4 . . ? C50 C55 H55A 108.4 . . ? C57 C55 H55B 108.4 . . ? C50 C55 H55B 108.4 . . ? H55A C55 H55B 107.5 . . ? O6 C56 C61 118.4(5) . . ? O6 C56 C57 118.9(6) . . ? C61 C56 C57 122.5(6) . . ? C56 C57 C58 117.3(6) . . ? C56 C57 C55 122.4(6) . . ? C58 C57 C55 120.2(6) . . ? C59 C58 C57 120.4(6) . . ? C59 C58 H58 119.8 . . ? C57 C58 H58 119.8 . . ? C58 C59 C60 122.1(6) . . ? C58 C59 Br6 118.5(5) . . ? C60 C59 Br6 119.5(5) . . ? C59 C60 C61 118.7(6) . . ? C59 C60 H60 120.6 . . ? C61 C60 H60 120.6 . . ? C56 C61 C60 118.9(6) . . ? C56 C61 C66 119.3(5) . . ? C60 C61 C66 121.6(6) . . ? O6 C62 C63 108.7(5) . . ? O6 C62 H62A 110.0 . . ? C63 C62 H62A 110.0 . . ? O6 C62 H62B 110.0 . . ? C63 C62 H62B 110.0 . . ? H62A C62 H62B 108.3 . . ? C62 C63 C64 114.3(6) . . ? C62 C63 H63A 108.7 . . ? C64 C63 H63A 108.7 . . ? C62 C63 H63B 108.7 . . ? C64 C63 H63B 108.7 . . ? H63A C63 H63B 107.6 . . ? C63 C64 C65 112.3(6) . . ? C63 C64 H64A 109.1 . . ? C65 C64 H64A 109.1 . . ? C63 C64 H64B 109.1 . . ? C65 C64 H64B 109.1 . . ? H64A C64 H64B 107.9 . . ? C64 C65 H65A 109.5 . . ? C64 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? C64 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? C68 C66 C61 115.4(5) . . ? C68 C66 H66A 108.4 . . ? C61 C66 H66A 108.4 . . ? C68 C66 H66B 108.4 . . ? C61 C66 H66B 108.4 . . ? H66A C66 H66B 107.5 . . ? O7 C67 C72 122.8(6) . . ? O7 C67 C68 116.5(6) . . ? C72 C67 C68 120.6(6) . . ? C69 C68 C67 118.9(6) . . ? C69 C68 C66 121.1(6) . . ? C67 C68 C66 120.0(6) . . ? C70 C69 C68 120.5(6) . . ? C70 C69 H69 119.8 . . ? C68 C69 H69 119.8 . . ? C69 C70 C71 121.2(7) . . ? C69 C70 Br7 120.1(6) . . ? C71 C70 Br7 118.6(5) . . ? C70 C71 C72 119.9(6) . . ? C70 C71 H71 120.0 . . ? C72 C71 H71 120.0 . . ? C71 C72 C67 118.8(6) . . ? C71 C72 C77 118.9(6) . . ? C67 C72 C77 122.3(6) . . ? O7 C73 C74 110.5(7) . . ? O7 C73 H73A 109.5 . . ? C74 C73 H73A 109.6 . . ? O7 C73 H73B 109.5 . . ? C74 C73 H73B 109.5 . . ? H73A C73 H73B 108.1 . . ? C73 C74 C75 116.6(9) . . ? C73 C74 H74A 108.2 . . ? C75 C74 H74A 108.1 . . ? C73 C74 H74B 108.1 . . ? C75 C74 H74B 108.1 . . ? H74A C74 H74B 107.3 . . ? C74 C75 C76 114.4(8) . . ? C74 C75 H75A 108.7 . . ? C76 C75 H75A 108.7 . . ? C74 C75 H75B 108.7 . . ? C76 C75 H75B 108.7 . . ? H75A C75 H75B 107.6 . . ? C75 C76 H76A 109.5 . . ? C75 C76 H76B 109.5 . . ? H76A C76 H76B 109.5 . . ? C75 C76 H76C 109.5 . . ? H76A C76 H76C 109.5 . . ? H76B C76 H76C 109.5 . . ? C72 C77 C79 112.7(5) . . ? C72 C77 H77A 109.1 . . ? C79 C77 H77A 109.1 . . ? C72 C77 H77B 109.1 . . ? C79 C77 H77B 109.1 . . ? H77A C77 H77B 107.8 . . ? C79 C78 O8 119.0(6) . . ? C79 C78 C83 122.1(6) . . ? O8 C78 C83 118.9(6) . . ? C78 C79 C80 118.1(6) . . ? C78 C79 C77 121.8(5) . . ? C80 C79 C77 120.1(6) . . ? C81 C80 C79 120.2(6) . . ? C81 C80 H80 119.9 . . ? C79 C80 H80 119.9 . . ? C80 C81 C82 121.3(6) . . ? C80 C81 Br8 119.6(5) . . ? C82 C81 Br8 119.1(5) . . ? C81 C82 C83 119.3(6) . . ? C81 C82 H82 120.3 . . ? C83 C82 H82 120.3 . . ? C82 C83 C78 118.8(6) . . ? C82 C83 C88 120.7(6) . . ? C78 C83 C88 120.5(6) . . ? C85A C84 O8 110.1(13) . . ? C85A C84 C85B 37.3(13) . . ? O8 C84 C85B 105.1(8) . . ? C85A C84 H84A 109.6 . . ? O8 C84 H84A 109.6 . . ? C85B C84 H84A 77.4 . . ? C85A C84 H84B 109.7 . . ? O8 C84 H84B 109.6 . . ? C85B C84 H84B 139.9 . . ? H84A C84 H84B 108.2 . . ? C86A C85A C84 130(2) . . ? C86A C85A H85A 104.9 . . ? C84 C85A H85A 104.9 . . ? C86A C85A H85B 104.8 . . ? C84 C85A H85B 104.8 . . ? H85A C85A H85B 105.8 . . ? C85A C86A C87 105(2) . . ? C85A C86A H86A 110.7 . . ? C87 C86A H86A 110.8 . . ? C85A C86A H86B 110.8 . . ? C87 C86A H86B 110.8 . . ? H86A C86A H86B 108.9 . . ? C84 C85B C86B 95.9(12) . . ? C84 C85B H85C 112.6 . . ? C86B C85B H85C 112.6 . . ? C84 C85B H85D 112.6 . . ? C86B C85B H85D 112.5 . . ? H85C C85B H85D 110.1 . . ? C87 C86B C85B 112(2) . . ? C87 C86B H86C 109.1 . . ? C85B C86B H86C 109.2 . . ? C87 C86B H86D 109.2 . . ? C85B C86B H86D 109.2 . . ? H86C C86B H86D 107.9 . . ? C86B C87 C86A 40.7(13) . . ? C86B C87 H87A 139.9 . . ? C86A C87 H87A 109.4 . . ? C86B C87 H87B 72.8 . . ? C86A C87 H87B 109.5 . . ? H87A C87 H87B 109.5 . . ? C86B C87 H87C 106.8 . . ? C86A C87 H87C 109.5 . . ? H87A C87 H87C 109.5 . . ? H87B C87 H87C 109.5 . . ? C83 C88 C46 113.1(5) . 2_665 ? C83 C88 H88A 109.0 . . ? C46 C88 H88A 109.0 2_665 . ? C83 C88 H88B 109.0 . . ? C46 C88 H88B 109.0 2_665 . ? H88A C88 H88B 107.8 . . ? C1 O1 C7 116.8(5) . . ? C12 O2 C18 112.2(5) . . ? C23 O3 C29 115.2(5) . . ? C34 O4 C40 113.3(5) . . ? C45 O5 C51 115.1(5) . . ? C56 O6 C62 113.1(5) . . ? C67 O7 C73 120.2(5) . . ? C78 O8 C84 112.7(5) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 4.761 _refine_diff_density_min -1.844 _refine_diff_density_rms 0.161