# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-gf-118K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-gf, 118 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Cl3 O3' _chemical_formula_sum 'C33 H33 Cl3 O3' _chemical_formula_weight 583.94 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 19.0393(3) _cell_length_b 13.3551(2) _cell_length_c 24.7011(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.139(2) _cell_angle_gamma 90.00 _cell_volume 5896.77(17) _cell_formula_units_Z 8 _cell_measurement_reflns_used 21222 _cell_measurement_temperature 118(2) _cell_measurement_theta_max 29.1675 _cell_measurement_theta_min 3.8013 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.95904 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2448 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_unetI/netI 0.0414 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 67739 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.23 _diffrn_reflns_theta_min 3.81 _diffrn_ambient_temperature 118(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.900 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0090722000 _diffrn_orient_matrix_UB_12 -0.0508825000 _diffrn_orient_matrix_UB_13 -0.0025344000 _diffrn_orient_matrix_UB_21 0.0289315000 _diffrn_orient_matrix_UB_22 0.0027207000 _diffrn_orient_matrix_UB_23 0.0272772000 _diffrn_orient_matrix_UB_31 -0.0256021000 _diffrn_orient_matrix_UB_32 -0.0149417000 _diffrn_orient_matrix_UB_33 0.0136066000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 10836 _reflns_number_total 14417 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.864 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.057 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 14417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0452 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+3.4038P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0999 _refine_ls_wR_factor_ref 0.1093 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C63(H63A,H63B), C47(H47A,H47B), C14(H14A,H14B), C54(H54A, H54B), C61(H61A,H61B), C40(H40A,H40B), C7(H7A,H7B), C30(H30A,H30B), C28(H28A, H28B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C42(H42), C50(H50), C13(H13), C43(H43), C60(H60), C53(H53), C46(H46), C49(H49), C56(H56), C12(H12), C10(H10), C16(H16), C20(H20), C17(H17), C9(H9), C23(H23), C57(H57), C59(H59), C45(H45), C27(H27), C26(H26), C52(H52), C19(H19), C24(H24) 2.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C29(H29A,H29B, H29C), C31(H31A,H31B,H31C), C62(H62A,H62B,H62C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl2 Cl 0.45536(3) 0.18383(4) 0.71545(2) 0.02901(11) Uani 1 1 d . . . Cl5 Cl -0.01011(3) 0.15171(4) 0.73588(2) 0.03297(12) Uani 1 1 d . . . Cl1 Cl 1.02468(3) 0.99929(3) 0.59198(3) 0.03669(14) Uani 1 1 d . . . Cl3 Cl 0.65916(3) -0.03768(4) 0.22352(2) 0.03433(12) Uani 1 1 d . . . Cl6 Cl 0.16520(3) -0.06367(4) 0.21439(2) 0.03764(13) Uani 1 1 d . . . Cl4 Cl 0.53535(3) 0.99983(4) 0.60499(3) 0.04899(17) Uani 1 1 d . . . O5 O 0.18896(7) 0.29886(10) 0.61707(5) 0.0234(3) Uani 1 1 d . . . O2 O 0.68122(6) 0.29251(10) 0.61255(5) 0.0204(3) Uani 1 1 d . . . O1 O 0.90208(7) 0.59067(9) 0.55769(5) 0.0219(3) Uani 1 1 d . . . O3 O 0.75966(7) 0.22727(9) 0.42621(5) 0.0214(3) Uani 1 1 d . . . C4 C 0.80076(9) 0.24335(12) 0.55609(7) 0.0152(3) Uani 1 1 d . . . O4 O 0.41715(7) 0.58891(9) 0.57678(5) 0.0214(3) Uani 1 1 d . . . C37 C 0.28957(9) 0.25654(13) 0.54410(8) 0.0170(3) Uani 1 1 d . . . O6 O 0.23262(7) 0.22413(9) 0.40539(5) 0.0223(3) Uani 1 1 d . . . C41 C 0.44197(9) 0.68594(13) 0.58019(8) 0.0180(3) Uani 1 1 d . . . C5 C 0.83884(9) 0.27844(13) 0.52027(7) 0.0164(3) Uani 1 1 d . . . C1 C 0.88161(9) 0.42329(13) 0.58259(7) 0.0164(3) Uani 1 1 d . . . C3 C 0.80096(9) 0.30079(13) 0.60350(7) 0.0152(3) Uani 1 1 d . . . C48 C 0.14727(10) 0.26262(13) 0.64815(8) 0.0184(3) Uani 1 1 d . . . C55 C 0.22144(9) 0.15791(13) 0.36080(7) 0.0179(3) Uani 1 1 d . . . C42 C 0.41415(10) 0.75653(13) 0.53703(8) 0.0215(4) Uani 1 1 d . . . H42 H 0.3758 0.7395 0.5031 0.026 Uiso 1 1 calc . . R C8 C 0.93633(9) 0.68276(13) 0.56818(7) 0.0171(3) Uani 1 1 d . . . C50 C 0.12767(11) 0.18226(13) 0.72893(8) 0.0224(4) Uani 1 1 d . . . H50 H 0.1465 0.1513 0.7648 0.027 Uiso 1 1 calc . . R C13 C 0.99558(10) 0.70784(13) 0.61764(8) 0.0192(4) Uani 1 1 d . . . H13 H 1.0166 0.6600 0.6460 0.023 Uiso 1 1 calc . . R C43 C 0.44369(10) 0.85297(14) 0.54450(9) 0.0269(4) Uani 1 1 d . . . H43 H 0.4254 0.9006 0.5155 0.032 Uiso 1 1 calc . . R C60 C 0.27788(10) 0.10523(14) 0.34999(8) 0.0228(4) Uani 1 1 d . . . H60 H 0.3274 0.1151 0.3733 0.027 Uiso 1 1 calc . . R C15 C 0.63159(9) 0.26580(13) 0.63957(7) 0.0173(3) Uani 1 1 d . . . C38 C 0.30540(9) 0.29460(13) 0.49648(7) 0.0176(3) Uani 1 1 d . . . C53 C 0.07009(10) 0.27490(14) 0.62210(8) 0.0232(4) Uani 1 1 d . . . H53 H 0.0509 0.3064 0.5864 0.028 Uiso 1 1 calc . . R C51 C 0.05144(10) 0.19443(13) 0.70219(8) 0.0218(4) Uani 1 1 d . . . C46 C 0.49989(10) 0.71134(14) 0.63083(8) 0.0224(4) Uani 1 1 d . . . H46 H 0.5192 0.6635 0.6595 0.027 Uiso 1 1 calc . . R C35 C 0.31462(9) 0.42111(13) 0.58946(7) 0.0168(3) Uani 1 1 d . . . C49 C 0.17606(10) 0.21692(13) 0.70167(8) 0.0200(4) Uani 1 1 d . . . H49 H 0.2275 0.2094 0.7193 0.024 Uiso 1 1 calc . . R C21 C 0.83463(9) 0.21753(13) 0.46770(7) 0.0192(4) Uani 1 1 d . . . H21A H 0.8709 0.2419 0.4513 0.023 Uiso 1 1 calc . . R H21B H 0.8456 0.1478 0.4782 0.023 Uiso 1 1 calc . . R C63 C 0.26749(10) 0.14710(13) 0.54449(8) 0.0207(4) Uani 1 1 d . . . H63A H 0.2410 0.1259 0.5052 0.025 Uiso 1 1 calc . . R H63B H 0.2335 0.1408 0.5659 0.025 Uiso 1 1 calc . . R C56 C 0.14709(10) 0.14332(14) 0.32575(8) 0.0215(4) Uani 1 1 d . . . H56 H 0.1091 0.1787 0.3328 0.026 Uiso 1 1 calc . . R C12 C 1.02326(10) 0.80579(14) 0.62443(8) 0.0218(4) Uani 1 1 d . . . H12 H 1.0625 0.8236 0.6576 0.026 Uiso 1 1 calc . . R C10 C 0.93498(10) 0.84986(14) 0.53147(9) 0.0255(4) Uani 1 1 d . . . H10 H 0.9154 0.8971 0.5025 0.031 Uiso 1 1 calc . . R C22 C 0.73991(10) 0.16318(13) 0.38003(7) 0.0184(3) Uani 1 1 d . . . C58 C 0.18699(10) 0.02344(14) 0.27056(8) 0.0231(4) Uani 1 1 d . . . C16 C 0.55642(10) 0.28690(14) 0.60899(8) 0.0214(4) Uani 1 1 d . . . H16 H 0.5429 0.3173 0.5730 0.026 Uiso 1 1 calc . . R C36 C 0.29402(9) 0.31984(13) 0.59023(7) 0.0167(3) Uani 1 1 d . . . C18 C 0.52332(10) 0.21749(13) 0.68593(8) 0.0199(4) Uani 1 1 d . . . C44 C 0.50038(10) 0.87757(14) 0.59519(9) 0.0277(4) Uani 1 1 d . . . C20 C 0.65209(10) 0.22151(13) 0.69343(7) 0.0189(4) Uani 1 1 d . . . H20 H 0.7021 0.2079 0.7139 0.023 Uiso 1 1 calc . . R C17 C 0.50207(10) 0.26274(14) 0.63219(8) 0.0222(4) Uani 1 1 d . . . H17 H 0.4520 0.2766 0.6120 0.027 Uiso 1 1 calc . . R C9 C 0.90719(10) 0.75292(13) 0.52476(8) 0.0215(4) Uani 1 1 d . . . H9 H 0.8689 0.7349 0.4911 0.026 Uiso 1 1 calc . . R C23 C 0.66418(10) 0.16060(14) 0.34634(8) 0.0230(4) Uani 1 1 d . . . H23 H 0.6304 0.2010 0.3559 0.028 Uiso 1 1 calc . . R C57 C 0.13016(10) 0.07620(14) 0.28061(8) 0.0244(4) Uani 1 1 d . . . H57 H 0.0807 0.0665 0.2570 0.029 Uiso 1 1 calc . . R C25 C 0.69002(11) 0.03872(14) 0.28481(8) 0.0230(4) Uani 1 1 d . . . C59 C 0.26085(10) 0.03777(15) 0.30453(8) 0.0250(4) Uani 1 1 d . . . H59 H 0.2987 0.0027 0.2971 0.030 Uiso 1 1 calc . . R C47 C 0.26853(9) 0.28212(14) 0.63804(8) 0.0193(4) Uani 1 1 d . . . H47A H 0.2798 0.2115 0.6452 0.023 Uiso 1 1 calc . . R H47B H 0.2925 0.3191 0.6734 0.023 Uiso 1 1 calc . . R C14 C 0.75814(9) 0.26412(14) 0.64102(7) 0.0183(3) Uani 1 1 d . . . H14A H 0.7624 0.1920 0.6454 0.022 Uiso 1 1 calc . . R H14B H 0.7777 0.2946 0.6789 0.022 Uiso 1 1 calc . . R C54 C 0.30646(10) 0.22556(13) 0.44859(8) 0.0201(4) Uani 1 1 d . . . H54A H 0.3426 0.2490 0.4318 0.024 Uiso 1 1 calc . . R H54B H 0.3206 0.1586 0.4636 0.024 Uiso 1 1 calc . . R C61 C 0.32601(10) 0.48614(14) 0.64217(8) 0.0228(4) Uani 1 1 d . . . H61A H 0.2864 0.4730 0.6576 0.027 Uiso 1 1 calc . . R H61B H 0.3231 0.5561 0.6311 0.027 Uiso 1 1 calc . . R C45 C 0.52859(10) 0.80755(15) 0.63846(9) 0.0268(4) Uani 1 1 d . . . H45 H 0.5666 0.8250 0.6725 0.032 Uiso 1 1 calc . . R C40 C 0.34261(9) 0.56988(13) 0.53683(8) 0.0195(4) Uani 1 1 d . . . H40A H 0.3396 0.5873 0.4980 0.023 Uiso 1 1 calc . . R H40B H 0.3065 0.6100 0.5469 0.023 Uiso 1 1 calc . . R C34 C 0.32592(9) 0.45970(13) 0.54008(7) 0.0173(3) Uani 1 1 d . . . C7 C 0.93126(10) 0.51440(13) 0.60012(7) 0.0192(4) Uani 1 1 d . . . H7A H 0.9324 0.5381 0.6375 0.023 Uiso 1 1 calc . . R H7B H 0.9819 0.4975 0.6028 0.023 Uiso 1 1 calc . . R C30 C 0.83773(10) 0.45362(13) 0.66764(7) 0.0197(4) Uani 1 1 d . . . H30A H 0.7894 0.4457 0.6721 0.024 Uiso 1 1 calc . . R H30B H 0.8440 0.5239 0.6604 0.024 Uiso 1 1 calc . . R C2 C 0.83948(9) 0.39209(12) 0.61637(7) 0.0154(3) Uani 1 1 d . . . C33 C 0.82119(12) 0.06016(14) 0.57700(9) 0.0284(4) Uani 1 1 d . . . H33A H 0.8633 0.0626 0.5641 0.043 Uiso 1 1 calc . . GR H33B H 0.7981 -0.0046 0.5687 0.043 Uiso 1 1 calc . . GR H33C H 0.8378 0.0720 0.6178 0.043 Uiso 1 1 calc . . GR C27 C 0.78993(10) 0.10231(14) 0.36589(8) 0.0235(4) Uani 1 1 d . . . H27 H 0.8404 0.1031 0.3885 0.028 Uiso 1 1 calc . . R C26 C 0.76486(11) 0.03998(15) 0.31785(9) 0.0267(4) Uani 1 1 d . . . H26 H 0.7985 -0.0005 0.3081 0.032 Uiso 1 1 calc . . R C28 C 0.92197(10) 0.40517(14) 0.49514(7) 0.0195(4) Uani 1 1 d . . . H28A H 0.9470 0.3493 0.4845 0.023 Uiso 1 1 calc . . R H28B H 0.9599 0.4528 0.5164 0.023 Uiso 1 1 calc . . R C6 C 0.88026(9) 0.36775(12) 0.53374(7) 0.0154(3) Uani 1 1 d . . . C32 C 0.76450(10) 0.14073(13) 0.54575(8) 0.0192(4) Uani 1 1 d . . . H32A H 0.7455 0.1267 0.5047 0.023 Uiso 1 1 calc . . R H32B H 0.7226 0.1397 0.5596 0.023 Uiso 1 1 calc . . R C11 C 0.99243(10) 0.87565(13) 0.58201(9) 0.0220(4) Uani 1 1 d . . . C64 C 0.33431(11) 0.07745(14) 0.57128(9) 0.0294(4) Uani 1 1 d . . . H64A H 0.3584 0.0944 0.6112 0.044 Uiso 1 1 calc . . GR H64B H 0.3692 0.0849 0.5512 0.044 Uiso 1 1 calc . . GR H64C H 0.3172 0.0093 0.5682 0.044 Uiso 1 1 calc . . GR C52 C 0.02201(10) 0.24040(14) 0.64904(8) 0.0233(4) Uani 1 1 d . . . H52 H -0.0294 0.2480 0.6316 0.028 Uiso 1 1 calc . . R C66 C 0.41112(11) 0.45277(16) 0.44510(9) 0.0308(4) Uani 1 1 d . . . H66A H 0.4366 0.3896 0.4538 0.046 Uiso 1 1 calc . . GR H66B H 0.4338 0.4991 0.4759 0.046 Uiso 1 1 calc . . GR H66C H 0.4146 0.4787 0.4099 0.046 Uiso 1 1 calc . . GR C19 C 0.59728(10) 0.19752(13) 0.71659(8) 0.0203(4) Uani 1 1 d . . . H19 H 0.6106 0.1680 0.7528 0.024 Uiso 1 1 calc . . R C24 C 0.63910(10) 0.09829(14) 0.29878(8) 0.0242(4) Uani 1 1 d . . . H24 H 0.5886 0.0964 0.2764 0.029 Uiso 1 1 calc . . R C29 C 0.86954(11) 0.45520(15) 0.44049(8) 0.0249(4) Uani 1 1 d . . . H29A H 0.8980 0.4785 0.4176 0.037 Uiso 1 1 calc . . GR H29B H 0.8449 0.5109 0.4509 0.037 Uiso 1 1 calc . . GR H29C H 0.8328 0.4077 0.4187 0.037 Uiso 1 1 calc . . GR C31 C 0.89936(10) 0.42179(15) 0.72355(8) 0.0250(4) Uani 1 1 d . . . H31A H 0.9474 0.4312 0.7196 0.037 Uiso 1 1 calc . . GR H31B H 0.8930 0.3525 0.7311 0.037 Uiso 1 1 calc . . GR H31C H 0.8963 0.4618 0.7550 0.037 Uiso 1 1 calc . . GR C65 C 0.32911(10) 0.43837(14) 0.43830(8) 0.0218(4) Uani 1 1 d . . . H65A H 0.3034 0.5022 0.4289 0.026 Uiso 1 1 calc . . R H65B H 0.3061 0.3928 0.4066 0.026 Uiso 1 1 calc . . R C39 C 0.31974(9) 0.39689(13) 0.49281(7) 0.0173(3) Uani 1 1 d . . . C62 C 0.40231(12) 0.46564(15) 0.68912(8) 0.0298(4) Uani 1 1 d . . . H62A H 0.4068 0.5051 0.7226 0.045 Uiso 1 1 calc . . GR H62B H 0.4417 0.4831 0.6749 0.045 Uiso 1 1 calc . . GR H62C H 0.4060 0.3959 0.6991 0.045 Uiso 1 1 calc . . GR 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 Cl2 0.0270(2) 0.0386(3) 0.0276(2) 0.0017(2) 0.01734(19) -0.0049(2) Cl5 0.0388(3) 0.0331(3) 0.0371(3) 0.0073(2) 0.0260(2) 0.0003(2) Cl1 0.0242(2) 0.0141(2) 0.0674(4) -0.0022(2) 0.0101(2) -0.00350(18) Cl3 0.0362(3) 0.0382(3) 0.0256(2) -0.0126(2) 0.0069(2) -0.0077(2) Cl6 0.0367(3) 0.0467(3) 0.0248(2) -0.0166(2) 0.0046(2) -0.0092(2) Cl4 0.0245(2) 0.0175(2) 0.0912(5) -0.0107(3) 0.0022(3) -0.0042(2) O5 0.0155(6) 0.0331(7) 0.0223(6) 0.0110(6) 0.0075(5) 0.0032(5) O2 0.0125(6) 0.0298(7) 0.0196(6) 0.0074(5) 0.0063(5) 0.0011(5) O1 0.0249(6) 0.0143(6) 0.0218(6) 0.0018(5) 0.0021(5) -0.0039(5) O3 0.0228(6) 0.0211(6) 0.0190(6) -0.0042(5) 0.0056(5) 0.0050(5) C4 0.0131(7) 0.0136(8) 0.0168(8) 0.0016(7) 0.0024(6) 0.0000(6) O4 0.0191(6) 0.0146(6) 0.0248(7) 0.0009(5) 0.0004(5) -0.0020(5) C37 0.0112(7) 0.0156(8) 0.0222(9) -0.0003(7) 0.0029(6) -0.0003(6) O6 0.0174(6) 0.0221(6) 0.0249(7) -0.0081(6) 0.0041(5) 0.0014(5) C41 0.0171(8) 0.0155(8) 0.0219(9) -0.0029(7) 0.0073(7) 0.0001(7) C5 0.0148(8) 0.0157(8) 0.0183(8) 0.0001(7) 0.0053(6) 0.0024(6) C1 0.0142(7) 0.0165(8) 0.0171(8) 0.0021(7) 0.0037(6) 0.0000(6) C3 0.0104(7) 0.0179(8) 0.0165(8) 0.0008(7) 0.0036(6) 0.0000(6) C48 0.0202(8) 0.0170(8) 0.0201(9) 0.0010(7) 0.0097(7) 0.0001(7) C55 0.0191(8) 0.0151(8) 0.0196(8) 0.0007(7) 0.0069(7) -0.0016(7) C42 0.0201(8) 0.0186(9) 0.0229(9) -0.0015(8) 0.0037(7) -0.0005(7) C8 0.0180(8) 0.0147(8) 0.0207(9) -0.0012(7) 0.0095(7) -0.0022(7) C50 0.0336(10) 0.0179(9) 0.0164(8) 0.0014(7) 0.0094(8) 0.0011(8) C13 0.0212(8) 0.0181(8) 0.0188(8) 0.0020(7) 0.0076(7) -0.0016(7) C43 0.0218(9) 0.0173(9) 0.0371(11) 0.0030(8) 0.0045(8) 0.0005(7) C60 0.0144(8) 0.0268(10) 0.0255(9) -0.0074(8) 0.0048(7) -0.0031(7) C15 0.0168(8) 0.0168(8) 0.0202(8) -0.0016(7) 0.0086(7) -0.0026(7) C38 0.0138(8) 0.0178(8) 0.0198(8) -0.0024(7) 0.0039(6) 0.0002(6) C53 0.0211(9) 0.0277(10) 0.0204(9) 0.0061(8) 0.0068(7) 0.0030(8) C51 0.0294(9) 0.0171(8) 0.0245(9) -0.0030(8) 0.0167(8) -0.0028(7) C46 0.0209(9) 0.0237(9) 0.0207(9) -0.0012(8) 0.0047(7) 0.0023(7) C35 0.0128(7) 0.0175(8) 0.0198(8) -0.0027(7) 0.0051(6) 0.0019(6) C49 0.0217(9) 0.0170(8) 0.0200(9) -0.0004(7) 0.0054(7) 0.0000(7) C21 0.0182(8) 0.0186(8) 0.0207(9) -0.0020(7) 0.0068(7) 0.0016(7) C63 0.0210(8) 0.0153(8) 0.0244(9) -0.0010(7) 0.0059(7) -0.0041(7) C56 0.0170(8) 0.0217(9) 0.0250(9) 0.0051(8) 0.0064(7) 0.0021(7) C12 0.0189(8) 0.0219(9) 0.0244(9) -0.0059(8) 0.0073(7) -0.0051(7) C10 0.0199(9) 0.0171(9) 0.0366(11) 0.0069(8) 0.0058(8) 0.0015(7) C22 0.0226(8) 0.0159(8) 0.0179(8) 0.0010(7) 0.0086(7) 0.0002(7) C58 0.0268(9) 0.0242(9) 0.0162(8) -0.0039(8) 0.0048(7) -0.0071(8) C16 0.0187(8) 0.0255(9) 0.0201(9) 0.0046(8) 0.0069(7) 0.0006(7) C36 0.0122(7) 0.0184(8) 0.0189(8) 0.0005(7) 0.0047(6) 0.0011(6) C18 0.0211(8) 0.0199(9) 0.0230(9) -0.0037(8) 0.0133(7) -0.0050(7) C44 0.0182(9) 0.0160(9) 0.0467(12) -0.0081(9) 0.0085(8) -0.0016(7) C20 0.0175(8) 0.0196(8) 0.0184(8) -0.0001(7) 0.0047(7) -0.0019(7) C17 0.0160(8) 0.0253(9) 0.0259(9) -0.0006(8) 0.0076(7) -0.0004(7) C9 0.0164(8) 0.0195(9) 0.0250(9) 0.0018(8) 0.0023(7) -0.0006(7) C23 0.0226(9) 0.0234(9) 0.0226(9) 0.0022(8) 0.0075(7) 0.0074(7) C57 0.0181(8) 0.0272(10) 0.0223(9) 0.0038(8) -0.0001(7) -0.0039(7) C25 0.0283(9) 0.0219(9) 0.0185(9) -0.0027(8) 0.0076(7) -0.0056(8) C59 0.0205(9) 0.0286(10) 0.0263(10) -0.0079(8) 0.0087(8) -0.0022(8) C47 0.0150(8) 0.0212(9) 0.0202(9) 0.0008(7) 0.0041(7) 0.0006(7) C14 0.0133(8) 0.0223(9) 0.0172(8) 0.0017(7) 0.0025(6) -0.0001(7) C54 0.0189(8) 0.0180(8) 0.0227(9) -0.0052(7) 0.0063(7) -0.0013(7) C61 0.0275(9) 0.0185(9) 0.0226(9) -0.0033(8) 0.0088(8) 0.0022(7) C45 0.0153(8) 0.0289(10) 0.0312(10) -0.0128(9) 0.0014(7) -0.0014(8) C40 0.0173(8) 0.0164(8) 0.0212(9) -0.0021(7) 0.0019(7) 0.0001(7) C34 0.0136(7) 0.0156(8) 0.0212(8) -0.0006(7) 0.0038(6) 0.0011(6) C7 0.0196(8) 0.0190(9) 0.0175(8) 0.0018(7) 0.0045(7) -0.0026(7) C30 0.0206(8) 0.0189(8) 0.0196(9) -0.0023(7) 0.0071(7) 0.0003(7) C2 0.0132(7) 0.0164(8) 0.0156(8) -0.0003(7) 0.0037(6) 0.0009(6) C33 0.0376(11) 0.0158(9) 0.0303(10) 0.0025(8) 0.0099(9) 0.0006(8) C27 0.0183(8) 0.0260(10) 0.0266(10) -0.0066(8) 0.0083(7) -0.0020(7) C26 0.0242(9) 0.0272(10) 0.0318(10) -0.0105(9) 0.0137(8) -0.0024(8) C28 0.0180(8) 0.0218(9) 0.0199(9) 0.0003(7) 0.0082(7) -0.0015(7) C6 0.0118(7) 0.0172(8) 0.0161(8) 0.0028(7) 0.0033(6) 0.0012(6) C32 0.0206(8) 0.0164(8) 0.0195(8) -0.0004(7) 0.0054(7) -0.0050(7) C11 0.0171(8) 0.0136(8) 0.0373(11) -0.0019(8) 0.0118(8) -0.0018(7) C64 0.0317(10) 0.0167(9) 0.0334(11) 0.0006(8) 0.0033(9) 0.0019(8) C52 0.0200(9) 0.0233(9) 0.0278(10) 0.0001(8) 0.0097(8) 0.0015(7) C66 0.0304(10) 0.0344(11) 0.0311(11) -0.0012(9) 0.0151(9) -0.0055(9) C19 0.0266(9) 0.0185(8) 0.0163(8) -0.0005(7) 0.0080(7) -0.0030(7) C24 0.0208(9) 0.0267(10) 0.0214(9) 0.0038(8) 0.0027(7) 0.0012(8) C29 0.0279(10) 0.0291(10) 0.0174(9) 0.0045(8) 0.0076(7) -0.0005(8) C31 0.0238(9) 0.0284(10) 0.0200(9) -0.0033(8) 0.0041(7) -0.0003(8) C65 0.0240(9) 0.0203(9) 0.0183(9) -0.0005(7) 0.0038(7) -0.0017(7) C39 0.0116(7) 0.0189(8) 0.0201(8) 0.0001(7) 0.0039(6) 0.0004(6) C62 0.0354(11) 0.0235(10) 0.0236(10) -0.0064(8) 0.0012(8) -0.0015(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl2 C18 1.7486(17) . ? Cl5 C51 1.7500(18) . ? Cl1 C11 1.7493(18) . ? Cl3 C25 1.7507(19) . ? Cl6 C58 1.7477(18) . ? Cl4 C44 1.7484(19) . ? O5 C48 1.369(2) . ? O5 C47 1.440(2) . ? O2 C15 1.378(2) . ? O2 C14 1.4402(19) . ? O1 C8 1.374(2) . ? O1 C7 1.430(2) . ? O3 C21 1.448(2) . ? O3 C22 1.371(2) . ? C4 C5 1.403(2) . ? C4 C3 1.399(2) . ? C4 C32 1.516(2) . ? O4 C41 1.372(2) . ? O4 C40 1.445(2) . ? C37 C38 1.406(2) . ? C37 C63 1.522(2) . ? C37 C36 1.398(2) . ? O6 C55 1.371(2) . ? O6 C54 1.443(2) . ? C41 C42 1.385(3) . ? C41 C46 1.395(2) . ? C5 C21 1.511(2) . ? C5 C6 1.405(2) . ? C1 C7 1.510(2) . ? C1 C2 1.405(2) . ? C1 C6 1.409(2) . ? C3 C14 1.511(2) . ? C3 C2 1.402(2) . ? C48 C53 1.396(2) . ? C48 C49 1.386(2) . ? C55 C60 1.385(2) . ? C55 C56 1.396(2) . ? C42 C43 1.392(3) . ? C8 C13 1.389(2) . ? C8 C9 1.388(2) . ? C50 C51 1.382(3) . ? C50 C49 1.394(3) . ? C13 C12 1.399(2) . ? C43 C44 1.382(3) . ? C60 C59 1.388(3) . ? C15 C16 1.398(2) . ? C15 C20 1.384(2) . ? C38 C54 1.505(2) . ? C38 C39 1.402(2) . ? C53 C52 1.383(3) . ? C51 C52 1.381(3) . ? C46 C45 1.384(3) . ? C35 C36 1.410(2) . ? C35 C61 1.517(2) . ? C35 C34 1.407(2) . ? C63 C64 1.530(3) . ? C56 C57 1.380(3) . ? C12 C11 1.375(3) . ? C10 C9 1.387(3) . ? C10 C11 1.390(3) . ? C22 C23 1.395(2) . ? C22 C27 1.385(2) . ? C58 C57 1.383(3) . ? C58 C59 1.380(3) . ? C16 C17 1.383(2) . ? C36 C47 1.510(2) . ? C18 C17 1.386(3) . ? C18 C19 1.376(3) . ? C44 C45 1.382(3) . ? C20 C19 1.389(2) . ? C23 C24 1.384(3) . ? C25 C26 1.377(3) . ? C25 C24 1.387(3) . ? C61 C62 1.540(3) . ? C40 C34 1.513(2) . ? C34 C39 1.409(2) . ? C30 C2 1.520(2) . ? C30 C31 1.533(2) . ? C33 C32 1.531(3) . ? C27 C26 1.392(3) . ? C28 C6 1.520(2) . ? C28 C29 1.529(2) . ? C66 C65 1.524(3) . ? C65 C39 1.522(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C48 O5 C47 119.00(13) . . ? C15 O2 C14 116.55(13) . . ? C8 O1 C7 117.39(13) . . ? C22 O3 C21 116.99(13) . . ? C5 C4 C32 119.98(15) . . ? C3 C4 C5 119.44(15) . . ? C3 C4 C32 120.44(15) . . ? C41 O4 C40 116.40(13) . . ? C38 C37 C63 119.46(15) . . ? C36 C37 C38 119.55(16) . . ? C36 C37 C63 121.00(16) . . ? C55 O6 C54 116.42(13) . . ? O4 C41 C42 124.29(16) . . ? O4 C41 C46 115.72(16) . . ? C42 C41 C46 119.98(17) . . ? C4 C5 C21 118.42(15) . . ? C4 C5 C6 120.25(15) . . ? C6 C5 C21 121.32(15) . . ? C2 C1 C7 119.85(15) . . ? C2 C1 C6 120.44(15) . . ? C6 C1 C7 119.66(15) . . ? C4 C3 C14 119.29(15) . . ? C4 C3 C2 121.15(15) . . ? C2 C3 C14 119.56(15) . . ? O5 C48 C53 114.93(15) . . ? O5 C48 C49 125.11(16) . . ? C49 C48 C53 119.95(16) . . ? O6 C55 C60 124.50(15) . . ? O6 C55 C56 115.62(15) . . ? C60 C55 C56 119.87(16) . . ? C41 C42 C43 119.87(17) . . ? O1 C8 C13 124.80(16) . . ? O1 C8 C9 114.90(15) . . ? C9 C8 C13 120.30(16) . . ? C51 C50 C49 119.35(17) . . ? C8 C13 C12 119.31(17) . . ? C44 C43 C42 119.59(18) . . ? C55 C60 C59 120.33(16) . . ? O2 C15 C16 115.55(15) . . ? O2 C15 C20 124.24(15) . . ? C20 C15 C16 120.21(16) . . ? C37 C38 C54 120.05(16) . . ? C39 C38 C37 120.58(16) . . ? C39 C38 C54 119.37(16) . . ? C52 C53 C48 120.33(17) . . ? C50 C51 Cl5 119.97(14) . . ? C52 C51 Cl5 118.55(14) . . ? C52 C51 C50 121.48(16) . . ? C45 C46 C41 120.08(18) . . ? C36 C35 C61 119.71(16) . . ? C34 C35 C36 119.29(15) . . ? C34 C35 C61 120.99(16) . . ? C48 C49 C50 119.78(17) . . ? O3 C21 C5 107.92(13) . . ? C37 C63 C64 113.34(15) . . ? C57 C56 C55 119.80(17) . . ? C11 C12 C13 119.94(17) . . ? C9 C10 C11 119.23(17) . . ? O3 C22 C23 116.28(15) . . ? O3 C22 C27 124.11(16) . . ? C27 C22 C23 119.61(16) . . ? C57 C58 Cl6 119.67(14) . . ? C59 C58 Cl6 119.24(15) . . ? C59 C58 C57 121.09(17) . . ? C17 C16 C15 120.13(17) . . ? C37 C36 C35 120.54(16) . . ? C37 C36 C47 119.37(15) . . ? C35 C36 C47 119.77(15) . . ? C17 C18 Cl2 119.83(14) . . ? C19 C18 Cl2 118.99(14) . . ? C19 C18 C17 121.18(16) . . ? C43 C44 Cl4 119.26(16) . . ? C45 C44 Cl4 119.78(15) . . ? C45 C44 C43 120.95(17) . . ? C15 C20 C19 119.43(16) . . ? C16 C17 C18 119.04(17) . . ? C10 C9 C8 120.23(17) . . ? C24 C23 C22 120.33(17) . . ? C56 C57 C58 119.77(17) . . ? C26 C25 Cl3 119.37(15) . . ? C26 C25 C24 121.00(17) . . ? C24 C25 Cl3 119.62(14) . . ? C58 C59 C60 119.14(17) . . ? O5 C47 C36 104.39(13) . . ? O2 C14 C3 106.73(13) . . ? O6 C54 C38 108.42(13) . . ? C35 C61 C62 111.32(15) . . ? C44 C45 C46 119.53(17) . . ? O4 C40 C34 108.03(13) . . ? C35 C34 C40 119.97(15) . . ? C35 C34 C39 120.40(16) . . ? C39 C34 C40 119.60(16) . . ? O1 C7 C1 108.48(14) . . ? C2 C30 C31 111.79(14) . . ? C1 C2 C30 121.02(15) . . ? C3 C2 C1 118.97(15) . . ? C3 C2 C30 119.96(15) . . ? C22 C27 C26 120.13(17) . . ? C25 C26 C27 119.58(17) . . ? C6 C28 C29 111.98(14) . . ? C5 C6 C1 119.53(15) . . ? C5 C6 C28 120.16(15) . . ? C1 C6 C28 120.31(15) . . ? C4 C32 C33 110.44(14) . . ? C12 C11 Cl1 119.76(14) . . ? C12 C11 C10 120.91(17) . . ? C10 C11 Cl1 119.32(14) . . ? C51 C52 C53 119.10(17) . . ? C18 C19 C20 120.01(16) . . ? C23 C24 C25 119.34(17) . . ? C39 C65 C66 112.10(15) . . ? C38 C39 C34 119.28(16) . . ? C38 C39 C65 119.76(15) . . ? C34 C39 C65 120.96(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 Cl2 C18 C17 C16 -178.63(14) . . . . ? Cl2 C18 C19 C20 178.54(13) . . . . ? Cl5 C51 C52 C53 179.70(14) . . . . ? Cl3 C25 C26 C27 178.56(15) . . . . ? Cl3 C25 C24 C23 -178.19(14) . . . . ? Cl6 C58 C57 C56 178.52(14) . . . . ? Cl6 C58 C59 C60 -178.46(15) . . . . ? Cl4 C44 C45 C46 179.00(15) . . . . ? O5 C48 C53 C52 179.34(17) . . . . ? O5 C48 C49 C50 -179.49(16) . . . . ? O2 C15 C16 C17 179.77(16) . . . . ? O2 C15 C20 C19 -179.91(16) . . . . ? O1 C8 C13 C12 -176.91(16) . . . . ? O1 C8 C9 C10 177.22(16) . . . . ? O3 C22 C23 C24 179.86(16) . . . . ? O3 C22 C27 C26 -179.53(17) . . . . ? C4 C5 C21 O3 71.35(19) . . . . ? C4 C5 C6 C1 -1.8(2) . . . . ? C4 C5 C6 C28 179.51(15) . . . . ? C4 C3 C14 O2 -82.13(18) . . . . ? C4 C3 C2 C1 -3.3(2) . . . . ? C4 C3 C2 C30 179.08(15) . . . . ? O4 C41 C42 C43 -179.38(17) . . . . ? O4 C41 C46 C45 -179.76(16) . . . . ? O4 C40 C34 C35 70.51(19) . . . . ? O4 C40 C34 C39 -111.26(17) . . . . ? C37 C38 C54 O6 91.44(18) . . . . ? C37 C38 C39 C34 6.6(2) . . . . ? C37 C38 C39 C65 -173.94(15) . . . . ? C37 C36 C47 O5 -84.40(18) . . . . ? O6 C55 C60 C59 178.37(17) . . . . ? O6 C55 C56 C57 -178.43(16) . . . . ? C41 O4 C40 C34 -179.42(14) . . . . ? C41 C42 C43 C44 -0.4(3) . . . . ? C41 C46 C45 C44 -1.2(3) . . . . ? C5 C4 C3 C14 178.34(15) . . . . ? C5 C4 C3 C2 -1.0(2) . . . . ? C5 C4 C32 C33 86.50(19) . . . . ? C3 C4 C5 C21 -177.04(15) . . . . ? C3 C4 C5 C6 3.5(2) . . . . ? C3 C4 C32 C33 -89.16(19) . . . . ? C48 O5 C47 C36 173.14(14) . . . . ? C48 C53 C52 C51 0.5(3) . . . . ? C55 O6 C54 C38 -174.33(14) . . . . ? C55 C60 C59 C58 -0.4(3) . . . . ? C55 C56 C57 C58 0.3(3) . . . . ? C42 C41 C46 C45 1.3(3) . . . . ? C42 C43 C44 Cl4 -178.24(15) . . . . ? C42 C43 C44 C45 0.5(3) . . . . ? C8 O1 C7 C1 175.08(14) . . . . ? C8 C13 C12 C11 -0.9(3) . . . . ? C50 C51 C52 C53 0.0(3) . . . . ? C13 C8 C9 C10 -2.7(3) . . . . ? C13 C12 C11 Cl1 177.41(14) . . . . ? C13 C12 C11 C10 -1.6(3) . . . . ? C43 C44 C45 C46 0.3(3) . . . . ? C60 C55 C56 C57 0.2(3) . . . . ? C15 O2 C14 C3 179.77(14) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C15 C20 C19 C18 0.2(3) . . . . ? C38 C37 C63 C64 90.1(2) . . . . ? C38 C37 C36 C35 -0.3(2) . . . . ? C38 C37 C36 C47 173.04(15) . . . . ? C53 C48 C49 C50 0.8(3) . . . . ? C51 C50 C49 C48 -0.3(3) . . . . ? C46 C41 C42 C43 -0.5(3) . . . . ? C35 C36 C47 O5 89.04(18) . . . . ? C35 C34 C39 C38 -2.8(2) . . . . ? C35 C34 C39 C65 177.82(15) . . . . ? C49 C48 C53 C52 -0.9(3) . . . . ? C49 C50 C51 Cl5 -179.81(13) . . . . ? C49 C50 C51 C52 -0.1(3) . . . . ? C21 O3 C22 C23 168.65(15) . . . . ? C21 O3 C22 C27 -10.9(2) . . . . ? C21 C5 C6 C1 178.82(15) . . . . ? C21 C5 C6 C28 0.1(2) . . . . ? C63 C37 C38 C54 -4.9(2) . . . . ? C63 C37 C38 C39 174.63(15) . . . . ? C63 C37 C36 C35 179.93(15) . . . . ? C63 C37 C36 C47 -6.7(2) . . . . ? C56 C55 C60 C59 -0.2(3) . . . . ? C22 O3 C21 C5 -168.14(14) . . . . ? C22 C23 C24 C25 -0.2(3) . . . . ? C22 C27 C26 C25 -0.5(3) . . . . ? C16 C15 C20 C19 0.5(3) . . . . ? C36 C37 C38 C54 175.41(15) . . . . ? C36 C37 C38 C39 -5.1(2) . . . . ? C36 C37 C63 C64 -90.2(2) . . . . ? C36 C35 C61 C62 78.1(2) . . . . ? C36 C35 C34 C40 175.64(15) . . . . ? C36 C35 C34 C39 -2.6(2) . . . . ? C20 C15 C16 C17 -0.6(3) . . . . ? C17 C18 C19 C20 -0.9(3) . . . . ? C9 C8 C13 C12 3.0(3) . . . . ? C9 C10 C11 Cl1 -177.10(14) . . . . ? C9 C10 C11 C12 1.9(3) . . . . ? C23 C22 C27 C26 0.9(3) . . . . ? C57 C58 C59 C60 1.0(3) . . . . ? C59 C58 C57 C56 -0.9(3) . . . . ? C47 O5 C48 C53 -174.77(16) . . . . ? C47 O5 C48 C49 5.5(3) . . . . ? C14 O2 C15 C16 -175.06(15) . . . . ? C14 O2 C15 C20 5.4(2) . . . . ? C14 C3 C2 C1 177.38(15) . . . . ? C14 C3 C2 C30 -0.2(2) . . . . ? C54 O6 C55 C60 -10.5(2) . . . . ? C54 O6 C55 C56 168.08(15) . . . . ? C54 C38 C39 C34 -173.88(15) . . . . ? C54 C38 C39 C65 5.5(2) . . . . ? C61 C35 C36 C37 -174.45(15) . . . . ? C61 C35 C36 C47 12.2(2) . . . . ? C61 C35 C34 C40 -5.8(2) . . . . ? C61 C35 C34 C39 176.00(15) . . . . ? C40 O4 C41 C42 -22.8(2) . . . . ? C40 O4 C41 C46 158.24(15) . . . . ? C40 C34 C39 C38 179.03(15) . . . . ? C40 C34 C39 C65 -0.4(2) . . . . ? C34 C35 C36 C37 4.1(2) . . . . ? C34 C35 C36 C47 -169.22(15) . . . . ? C34 C35 C61 C62 -100.43(19) . . . . ? C7 O1 C8 C13 -2.0(2) . . . . ? C7 O1 C8 C9 178.10(15) . . . . ? C7 C1 C2 C3 -172.27(15) . . . . ? C7 C1 C2 C30 5.3(2) . . . . ? C7 C1 C6 C5 174.77(15) . . . . ? C7 C1 C6 C28 -6.5(2) . . . . ? C2 C1 C7 O1 -113.79(17) . . . . ? C2 C1 C6 C5 -2.6(2) . . . . ? C2 C1 C6 C28 176.13(15) . . . . ? C2 C3 C14 O2 97.20(17) . . . . ? C27 C22 C23 C24 -0.5(3) . . . . ? C26 C25 C24 C23 0.7(3) . . . . ? C6 C5 C21 O3 -109.22(17) . . . . ? C6 C1 C7 O1 68.8(2) . . . . ? C6 C1 C2 C3 5.1(2) . . . . ? C6 C1 C2 C30 -177.33(15) . . . . ? C32 C4 C5 C21 7.3(2) . . . . ? C32 C4 C5 C6 -172.18(15) . . . . ? C32 C4 C3 C14 -6.0(2) . . . . ? C32 C4 C3 C2 174.71(15) . . . . ? C11 C10 C9 C8 0.2(3) . . . . ? C66 C65 C39 C38 -100.31(19) . . . . ? C66 C65 C39 C34 79.1(2) . . . . ? C19 C18 C17 C16 0.8(3) . . . . ? C24 C25 C26 C27 -0.3(3) . . . . ? C29 C28 C6 C5 77.8(2) . . . . ? C29 C28 C6 C1 -100.87(19) . . . . ? C31 C30 C2 C1 -90.7(2) . . . . ? C31 C30 C2 C3 86.88(19) . . . . ? C39 C38 C54 O6 -88.05(18) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962405' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-gf-154K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-gf, 154 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Cl3 O3' _chemical_formula_sum 'C33 H33 Cl3 O3' _chemical_formula_weight 583.94 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 19.0690(7) _cell_length_b 13.3847(4) _cell_length_c 24.7369(9) _cell_angle_alpha 90.00 _cell_angle_beta 110.263(4) _cell_angle_gamma 90.00 _cell_volume 5922.9(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 7529 _cell_measurement_temperature 154(2) _cell_measurement_theta_max 29.1988 _cell_measurement_theta_min 3.9541 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90921 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2448 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_unetI/netI 0.0741 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 28969 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.26 _diffrn_reflns_theta_min 3.96 _diffrn_ambient_temperature 154(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.842 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0090078000 _diffrn_orient_matrix_UB_12 -0.0507925000 _diffrn_orient_matrix_UB_13 -0.0025457000 _diffrn_orient_matrix_UB_21 0.0289231000 _diffrn_orient_matrix_UB_22 0.0026974000 _diffrn_orient_matrix_UB_23 0.0272739000 _diffrn_orient_matrix_UB_31 -0.0255695000 _diffrn_orient_matrix_UB_32 -0.0148947000 _diffrn_orient_matrix_UB_33 0.0135601000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 8906 _reflns_number_total 13589 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.673 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.056 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 13589 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0892 _refine_ls_R_factor_gt 0.0506 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1133 _refine_ls_wR_factor_ref 0.1310 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C63(H63A,H63B), C47(H47A,H47B), C14(H14A,H14B), C54(H54A, H54B), C61(H61A,H61B), C40(H40A,H40B), C7(H7A,H7B), C30(H30A,H30B), C28(H28A, H28B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C42(H42), C50(H50), C13(H13), C43(H43), C60(H60), C53(H53), C46(H46), C49(H49), C56(H56), C12(H12), C10(H10), C16(H16), C20(H20), C17(H17), C9(H9), C23(H23), C57(H57), C59(H59), C45(H45), C27(H27), C26(H26), C52(H52), C19(H19), C24(H24) 2.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C29(H29A,H29B, H29C), C31(H31A,H31B,H31C), C62(H62A,H62B,H62C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl2 Cl 0.45681(3) 0.18362(5) 0.71515(3) 0.03824(16) Uani 1 1 d . . . Cl5 Cl -0.00919(4) 0.15232(5) 0.73573(3) 0.04334(17) Uani 1 1 d . . . Cl1 Cl 1.02481(3) 0.99789(4) 0.59210(3) 0.04782(19) Uani 1 1 d . . . Cl3 Cl 0.65879(4) -0.03624(5) 0.22381(3) 0.04586(18) Uani 1 1 d . . . Cl6 Cl 0.16460(4) -0.06117(6) 0.21461(3) 0.05034(19) Uani 1 1 d . . . Cl4 Cl 0.53512(4) 0.99785(5) 0.60514(4) 0.0638(3) Uani 1 1 d . . . O5 O 0.18918(8) 0.29762(12) 0.61693(6) 0.0301(4) Uani 1 1 d . . . O2 O 0.68169(7) 0.29237(11) 0.61231(6) 0.0260(3) Uani 1 1 d . . . O1 O 0.90191(8) 0.59035(10) 0.55796(6) 0.0277(4) Uani 1 1 d . . . O3 O 0.75987(8) 0.22820(11) 0.42615(6) 0.0265(3) Uani 1 1 d . . . C4 C 0.80076(11) 0.24356(15) 0.55582(8) 0.0188(4) Uani 1 1 d . . . O4 O 0.41718(8) 0.58791(10) 0.57698(6) 0.0275(4) Uani 1 1 d . . . C37 C 0.28981(11) 0.25580(15) 0.54438(9) 0.0213(5) Uani 1 1 d . . . O6 O 0.23285(8) 0.22396(11) 0.40596(6) 0.0284(4) Uani 1 1 d . . . C41 C 0.44200(11) 0.68501(15) 0.58051(9) 0.0218(5) Uani 1 1 d . . . C5 C 0.83906(11) 0.27907(15) 0.51995(8) 0.0194(4) Uani 1 1 d . . . C1 C 0.88172(11) 0.42321(15) 0.58260(9) 0.0205(4) Uani 1 1 d . . . C3 C 0.80114(11) 0.30102(15) 0.60313(8) 0.0189(4) Uani 1 1 d . . . C48 C 0.14764(12) 0.26211(15) 0.64807(9) 0.0234(5) Uani 1 1 d . . . C55 C 0.22164(11) 0.15795(15) 0.36137(9) 0.0228(5) Uani 1 1 d . . . C42 C 0.41432(12) 0.75504(16) 0.53764(9) 0.0273(5) Uani 1 1 d . . . H42 H 0.3759 0.7381 0.5038 0.033 Uiso 1 1 calc . . R C8 C 0.93621(11) 0.68221(15) 0.56849(9) 0.0208(4) Uani 1 1 d . . . C50 C 0.12790(13) 0.18252(16) 0.72855(9) 0.0284(5) Uani 1 1 d . . . H50 H 0.1468 0.1519 0.7644 0.034 Uiso 1 1 calc . . R C13 C 0.99568(12) 0.70726(16) 0.61795(9) 0.0237(5) Uani 1 1 d . . . H13 H 1.0168 0.6596 0.6463 0.028 Uiso 1 1 calc . . R C43 C 0.44388(13) 0.85111(17) 0.54506(11) 0.0347(6) Uani 1 1 d . . . H43 H 0.4254 0.8984 0.5160 0.042 Uiso 1 1 calc . . R C60 C 0.27762(12) 0.10606(17) 0.35028(9) 0.0285(5) Uani 1 1 d . . . H60 H 0.3272 0.1159 0.3734 0.034 Uiso 1 1 calc . . R C15 C 0.63216(11) 0.26563(15) 0.63914(9) 0.0217(5) Uani 1 1 d . . . C38 C 0.30572(11) 0.29390(15) 0.49702(9) 0.0223(5) Uani 1 1 d . . . C53 C 0.07087(12) 0.27387(17) 0.62220(10) 0.0299(5) Uani 1 1 d . . . H53 H 0.0516 0.3048 0.5864 0.036 Uiso 1 1 calc . . R C51 C 0.05191(13) 0.19437(16) 0.70200(9) 0.0260(5) Uani 1 1 d . . . C46 C 0.49973(12) 0.71037(17) 0.63089(9) 0.0291(5) Uani 1 1 d . . . H46 H 0.5191 0.6628 0.6596 0.035 Uiso 1 1 calc . . R C35 C 0.31472(11) 0.42012(15) 0.58973(9) 0.0208(5) Uani 1 1 d . . . C49 C 0.17639(12) 0.21662(15) 0.70143(9) 0.0244(5) Uani 1 1 d . . . H49 H 0.2278 0.2088 0.7191 0.029 Uiso 1 1 calc . . R C21 C 0.83462(12) 0.21796(16) 0.46747(9) 0.0241(5) Uani 1 1 d . . . H21A H 0.8709 0.2419 0.4511 0.029 Uiso 1 1 calc . . R H21B H 0.8453 0.1483 0.4780 0.029 Uiso 1 1 calc . . R C63 C 0.26800(12) 0.14669(15) 0.54483(9) 0.0268(5) Uani 1 1 d . . . H63A H 0.2414 0.1255 0.5055 0.032 Uiso 1 1 calc . . R H63B H 0.2341 0.1404 0.5662 0.032 Uiso 1 1 calc . . R C56 C 0.14743(12) 0.14360(17) 0.32660(9) 0.0274(5) Uani 1 1 d . . . H56 H 0.1096 0.1789 0.3338 0.033 Uiso 1 1 calc . . R C12 C 1.02324(12) 0.80484(16) 0.62460(10) 0.0285(5) Uani 1 1 d . . . H12 H 1.0624 0.8227 0.6578 0.034 Uiso 1 1 calc . . R C10 C 0.93521(12) 0.84886(17) 0.53218(11) 0.0323(6) Uani 1 1 d . . . H10 H 0.9155 0.8960 0.5033 0.039 Uiso 1 1 calc . . R C22 C 0.74010(12) 0.16395(16) 0.37984(9) 0.0236(5) Uani 1 1 d . . . C58 C 0.18652(13) 0.02513(17) 0.27092(9) 0.0294(5) Uani 1 1 d . . . C16 C 0.55726(12) 0.28699(17) 0.60918(9) 0.0267(5) Uani 1 1 d . . . H16 H 0.5435 0.3178 0.5733 0.032 Uiso 1 1 calc . . R C36 C 0.29412(11) 0.31940(15) 0.59033(9) 0.0205(4) Uani 1 1 d . . . C18 C 0.52468(12) 0.21711(16) 0.68561(9) 0.0249(5) Uani 1 1 d . . . C44 C 0.50038(12) 0.87616(17) 0.59531(11) 0.0347(6) Uani 1 1 d . . . C20 C 0.65275(12) 0.22117(16) 0.69284(9) 0.0245(5) Uani 1 1 d . . . H20 H 0.7028 0.2077 0.7133 0.029 Uiso 1 1 calc . . R C17 C 0.50351(12) 0.26280(17) 0.63229(9) 0.0279(5) Uani 1 1 d . . . H17 H 0.4535 0.2770 0.6123 0.034 Uiso 1 1 calc . . R C9 C 0.90719(12) 0.75234(16) 0.52528(10) 0.0277(5) Uani 1 1 d . . . H9 H 0.8688 0.7346 0.4916 0.033 Uiso 1 1 calc . . R C23 C 0.66456(12) 0.16179(17) 0.34625(9) 0.0296(5) Uani 1 1 d . . . H23 H 0.6310 0.2025 0.3557 0.036 Uiso 1 1 calc . . R C57 C 0.13031(12) 0.07696(17) 0.28147(9) 0.0312(5) Uani 1 1 d . . . H57 H 0.0808 0.0670 0.2582 0.037 Uiso 1 1 calc . . R C25 C 0.68966(13) 0.04059(17) 0.28495(9) 0.0300(5) Uani 1 1 d . . . C59 C 0.26015(13) 0.03946(18) 0.30482(10) 0.0317(5) Uani 1 1 d . . . H59 H 0.2979 0.0046 0.2972 0.038 Uiso 1 1 calc . . R C47 C 0.26890(11) 0.28179(17) 0.63802(9) 0.0247(5) Uani 1 1 d . . . H47A H 0.2806 0.2115 0.6454 0.030 Uiso 1 1 calc . . R H47B H 0.2927 0.3190 0.6733 0.030 Uiso 1 1 calc . . R C14 C 0.75864(11) 0.26405(16) 0.64048(9) 0.0231(5) Uani 1 1 d . . . H14A H 0.7629 0.1920 0.6447 0.028 Uiso 1 1 calc . . R H14B H 0.7783 0.2941 0.6785 0.028 Uiso 1 1 calc . . R C54 C 0.30640(11) 0.22553(16) 0.44891(9) 0.0250(5) Uani 1 1 d . . . H54A H 0.3423 0.2492 0.4321 0.030 Uiso 1 1 calc . . R H54B H 0.3208 0.1587 0.4637 0.030 Uiso 1 1 calc . . R C61 C 0.32585(13) 0.48491(16) 0.64234(9) 0.0288(5) Uani 1 1 d . . . H61A H 0.2861 0.4717 0.6574 0.035 Uiso 1 1 calc . . R H61B H 0.3229 0.5547 0.6312 0.035 Uiso 1 1 calc . . R C45 C 0.52823(12) 0.80602(18) 0.63834(10) 0.0339(6) Uani 1 1 d . . . H45 H 0.5662 0.8233 0.6724 0.041 Uiso 1 1 calc . . R C40 C 0.34280(11) 0.56868(16) 0.53749(9) 0.0251(5) Uani 1 1 d . . . H40A H 0.3393 0.5862 0.4986 0.030 Uiso 1 1 calc . . R H40B H 0.3069 0.6086 0.5478 0.030 Uiso 1 1 calc . . R C34 C 0.32620(11) 0.45874(15) 0.54064(9) 0.0218(5) Uani 1 1 d . . . C7 C 0.93119(12) 0.51398(15) 0.60002(9) 0.0242(5) Uani 1 1 d . . . H7A H 0.9327 0.5373 0.6375 0.029 Uiso 1 1 calc . . R H7B H 0.9817 0.4972 0.6025 0.029 Uiso 1 1 calc . . R C30 C 0.83837(12) 0.45302(16) 0.66723(9) 0.0251(5) Uani 1 1 d . . . H30A H 0.7900 0.4455 0.6716 0.030 Uiso 1 1 calc . . R H30B H 0.8448 0.5231 0.6601 0.030 Uiso 1 1 calc . . R C2 C 0.83957(11) 0.39219(15) 0.61603(8) 0.0192(4) Uani 1 1 d . . . C33 C 0.82104(14) 0.06107(16) 0.57642(11) 0.0366(6) Uani 1 1 d . . . H33A H 0.8624 0.0618 0.5627 0.055 Uiso 1 1 calc . . GR H33B H 0.7972 -0.0032 0.5690 0.055 Uiso 1 1 calc . . GR H33C H 0.8388 0.0739 0.6171 0.055 Uiso 1 1 calc . . GR C27 C 0.78939(12) 0.10352(17) 0.36554(10) 0.0303(5) Uani 1 1 d . . . H27 H 0.8399 0.1043 0.3880 0.036 Uiso 1 1 calc . . R C26 C 0.76421(13) 0.04124(18) 0.31760(10) 0.0348(6) Uani 1 1 d . . . H26 H 0.7975 0.0006 0.3078 0.042 Uiso 1 1 calc . . R C28 C 0.92178(11) 0.40552(16) 0.49514(9) 0.0245(5) Uani 1 1 d . . . H28A H 0.9596 0.4531 0.5165 0.029 Uiso 1 1 calc . . R H28B H 0.9469 0.3498 0.4846 0.029 Uiso 1 1 calc . . R C6 C 0.88008(11) 0.36799(15) 0.53354(8) 0.0193(4) Uani 1 1 d . . . C32 C 0.76505(12) 0.14136(15) 0.54542(9) 0.0248(5) Uani 1 1 d . . . H32A H 0.7462 0.1275 0.5044 0.030 Uiso 1 1 calc . . R H32B H 0.7231 0.1402 0.5590 0.030 Uiso 1 1 calc . . R C11 C 0.99250(12) 0.87465(16) 0.58212(10) 0.0284(5) Uani 1 1 d . . . C64 C 0.33434(14) 0.07738(17) 0.57143(11) 0.0383(6) Uani 1 1 d . . . H64A H 0.3579 0.0932 0.6115 0.057 Uiso 1 1 calc . . GR H64B H 0.3697 0.0859 0.5520 0.057 Uiso 1 1 calc . . GR H64C H 0.3173 0.0094 0.5675 0.057 Uiso 1 1 calc . . GR C52 C 0.02280(12) 0.24017(16) 0.64907(10) 0.0287(5) Uani 1 1 d . . . H52 H -0.0286 0.2483 0.6316 0.034 Uiso 1 1 calc . . R C66 C 0.41093(14) 0.4516(2) 0.44580(11) 0.0420(6) Uani 1 1 d . . . H66A H 0.4359 0.3881 0.4538 0.063 Uiso 1 1 calc . . GR H66B H 0.4339 0.4966 0.4772 0.063 Uiso 1 1 calc . . GR H66C H 0.4146 0.4787 0.4110 0.063 Uiso 1 1 calc . . GR C19 C 0.59822(12) 0.19683(16) 0.71591(9) 0.0253(5) Uani 1 1 d . . . H19 H 0.6116 0.1667 0.7520 0.030 Uiso 1 1 calc . . R C24 C 0.63913(13) 0.09953(17) 0.29891(9) 0.0310(5) Uani 1 1 d . . . H24 H 0.5886 0.0974 0.2767 0.037 Uiso 1 1 calc . . R C29 C 0.86983(13) 0.45511(18) 0.44073(9) 0.0328(6) Uani 1 1 d . . . H29A H 0.8984 0.4791 0.4182 0.049 Uiso 1 1 calc . . GR H29B H 0.8447 0.5101 0.4510 0.049 Uiso 1 1 calc . . GR H29C H 0.8336 0.4074 0.4187 0.049 Uiso 1 1 calc . . GR C31 C 0.89935(13) 0.42160(18) 0.72305(9) 0.0332(6) Uani 1 1 d . . . H31A H 0.9474 0.4307 0.7194 0.050 Uiso 1 1 calc . . GR H31B H 0.8928 0.3525 0.7307 0.050 Uiso 1 1 calc . . GR H31C H 0.8962 0.4618 0.7543 0.050 Uiso 1 1 calc . . GR C65 C 0.32921(12) 0.43780(17) 0.43870(9) 0.0278(5) Uani 1 1 d . . . H65A H 0.3061 0.3924 0.4070 0.033 Uiso 1 1 calc . . R H65B H 0.3037 0.5016 0.4293 0.033 Uiso 1 1 calc . . R C39 C 0.32012(11) 0.39639(16) 0.49341(9) 0.0217(5) Uani 1 1 d . . . C62 C 0.40157(14) 0.46486(18) 0.68949(10) 0.0397(6) Uani 1 1 d . . . H62A H 0.4055 0.5039 0.7230 0.060 Uiso 1 1 calc . . GR H62B H 0.4411 0.4830 0.6757 0.060 Uiso 1 1 calc . . GR H62C H 0.4055 0.3952 0.6993 0.060 Uiso 1 1 calc . . GR 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 Cl2 0.0352(3) 0.0506(4) 0.0372(3) 0.0024(3) 0.0231(3) -0.0061(3) Cl5 0.0518(4) 0.0426(4) 0.0492(4) 0.0094(3) 0.0348(3) 0.0007(3) Cl1 0.0323(3) 0.0181(3) 0.0868(5) -0.0029(3) 0.0126(3) -0.0047(3) Cl3 0.0494(4) 0.0493(4) 0.0341(3) -0.0174(3) 0.0084(3) -0.0102(3) Cl6 0.0499(4) 0.0612(5) 0.0335(3) -0.0228(3) 0.0062(3) -0.0121(4) Cl4 0.0323(4) 0.0222(3) 0.1186(7) -0.0138(4) 0.0031(4) -0.0057(3) O5 0.0206(8) 0.0415(10) 0.0288(8) 0.0129(7) 0.0093(6) 0.0036(7) O2 0.0169(7) 0.0377(9) 0.0242(8) 0.0088(7) 0.0080(6) 0.0005(7) O1 0.0328(9) 0.0165(7) 0.0282(8) 0.0022(6) 0.0034(7) -0.0056(7) O3 0.0288(8) 0.0248(8) 0.0253(8) -0.0055(6) 0.0085(6) 0.0065(7) C4 0.0164(10) 0.0176(10) 0.0197(10) 0.0002(8) 0.0028(8) -0.0005(9) O4 0.0254(8) 0.0182(8) 0.0331(8) 0.0006(6) 0.0029(7) -0.0031(7) C37 0.0146(10) 0.0178(11) 0.0294(11) 0.0006(9) 0.0047(8) 0.0003(9) O6 0.0240(8) 0.0274(8) 0.0314(8) -0.0090(7) 0.0064(6) 0.0034(7) C41 0.0221(11) 0.0173(11) 0.0276(11) -0.0037(9) 0.0106(9) -0.0018(9) C5 0.0179(10) 0.0187(10) 0.0209(10) 0.0001(8) 0.0058(8) 0.0033(9) C1 0.0193(10) 0.0189(11) 0.0220(10) 0.0010(8) 0.0055(8) -0.0008(9) C3 0.0157(10) 0.0199(11) 0.0207(10) 0.0003(8) 0.0056(8) -0.0016(9) C48 0.0269(11) 0.0207(11) 0.0244(11) 0.0012(9) 0.0113(9) 0.0000(10) C55 0.0239(11) 0.0198(11) 0.0247(11) 0.0001(9) 0.0085(9) -0.0021(10) C42 0.0253(11) 0.0223(12) 0.0298(12) -0.0014(9) 0.0037(9) -0.0021(10) C8 0.0210(11) 0.0175(11) 0.0270(11) -0.0022(9) 0.0124(9) -0.0024(9) C50 0.0412(14) 0.0215(11) 0.0216(11) 0.0019(9) 0.0099(10) 0.0020(11) C13 0.0260(11) 0.0217(11) 0.0245(11) 0.0024(9) 0.0102(9) -0.0033(10) C43 0.0286(13) 0.0209(12) 0.0501(15) 0.0047(11) 0.0077(11) 0.0007(11) C60 0.0184(11) 0.0340(13) 0.0318(12) -0.0108(10) 0.0070(9) -0.0045(10) C15 0.0223(11) 0.0224(11) 0.0219(10) -0.0016(9) 0.0097(8) -0.0045(10) C38 0.0189(10) 0.0204(11) 0.0266(11) -0.0035(9) 0.0066(8) 0.0011(9) C53 0.0272(12) 0.0338(13) 0.0287(12) 0.0103(10) 0.0097(9) 0.0050(11) C51 0.0348(13) 0.0208(11) 0.0282(11) -0.0019(9) 0.0183(10) -0.0025(10) C46 0.0261(12) 0.0311(13) 0.0272(12) -0.0029(10) 0.0053(9) 0.0016(11) C35 0.0152(10) 0.0209(11) 0.0256(11) -0.0028(9) 0.0060(8) 0.0040(9) C49 0.0272(11) 0.0209(11) 0.0229(11) -0.0001(9) 0.0060(9) -0.0002(10) C21 0.0262(11) 0.0215(11) 0.0256(11) -0.0027(9) 0.0104(9) 0.0022(10) C63 0.0263(12) 0.0193(11) 0.0322(12) -0.0008(9) 0.0069(9) -0.0048(10) C56 0.0234(11) 0.0270(12) 0.0309(12) 0.0070(10) 0.0082(9) 0.0051(10) C12 0.0261(12) 0.0280(12) 0.0313(12) -0.0076(10) 0.0097(9) -0.0074(11) C10 0.0242(12) 0.0220(12) 0.0467(14) 0.0094(11) 0.0072(10) 0.0021(10) C22 0.0271(11) 0.0210(11) 0.0240(11) 0.0001(9) 0.0106(9) 0.0003(10) C58 0.0334(13) 0.0313(13) 0.0210(11) -0.0059(10) 0.0063(9) -0.0110(11) C16 0.0247(11) 0.0311(13) 0.0249(11) 0.0044(10) 0.0093(9) -0.0006(10) C36 0.0168(10) 0.0203(11) 0.0240(10) -0.0001(9) 0.0064(8) 0.0006(9) C18 0.0277(12) 0.0237(12) 0.0292(11) -0.0047(9) 0.0172(9) -0.0069(10) C44 0.0224(12) 0.0196(12) 0.0586(16) -0.0107(11) 0.0098(11) -0.0019(10) C20 0.0245(11) 0.0242(12) 0.0235(11) 0.0008(9) 0.0068(9) -0.0030(10) C17 0.0224(11) 0.0313(13) 0.0312(12) 0.0015(10) 0.0107(9) 0.0015(10) C9 0.0213(11) 0.0248(12) 0.0327(12) 0.0026(10) 0.0038(9) -0.0011(10) C23 0.0287(12) 0.0316(13) 0.0283(12) 0.0027(10) 0.0095(9) 0.0096(11) C57 0.0250(12) 0.0341(13) 0.0270(12) 0.0034(10) -0.0007(9) -0.0042(11) C25 0.0360(13) 0.0274(12) 0.0249(11) -0.0055(10) 0.0086(10) -0.0073(11) C59 0.0265(12) 0.0357(13) 0.0342(13) -0.0099(11) 0.0123(10) -0.0020(11) C47 0.0182(10) 0.0272(12) 0.0264(11) 0.0007(9) 0.0047(8) 0.0014(10) C14 0.0159(10) 0.0289(12) 0.0218(10) 0.0013(9) 0.0031(8) -0.0020(10) C54 0.0234(11) 0.0208(11) 0.0307(12) -0.0051(9) 0.0092(9) -0.0009(10) C61 0.0358(13) 0.0226(12) 0.0282(12) -0.0031(9) 0.0111(10) 0.0034(11) C45 0.0200(11) 0.0368(14) 0.0400(14) -0.0157(11) 0.0040(10) -0.0027(11) C40 0.0225(11) 0.0212(11) 0.0275(11) -0.0015(9) 0.0035(9) -0.0013(10) C34 0.0185(10) 0.0182(11) 0.0279(11) -0.0017(9) 0.0070(8) 0.0017(9) C7 0.0260(11) 0.0247(12) 0.0196(10) 0.0031(9) 0.0049(9) -0.0025(10) C30 0.0269(11) 0.0238(12) 0.0257(11) -0.0034(9) 0.0104(9) 0.0008(10) C2 0.0188(10) 0.0194(11) 0.0190(10) -0.0013(8) 0.0059(8) 0.0018(9) C33 0.0475(15) 0.0179(11) 0.0421(14) 0.0030(10) 0.0127(12) 0.0009(12) C27 0.0231(11) 0.0328(13) 0.0354(13) -0.0100(11) 0.0107(10) -0.0010(11) C26 0.0311(13) 0.0347(14) 0.0414(14) -0.0146(11) 0.0163(11) -0.0021(12) C28 0.0219(11) 0.0279(12) 0.0243(11) -0.0003(9) 0.0089(9) -0.0023(10) C6 0.0154(10) 0.0202(11) 0.0210(10) 0.0035(8) 0.0047(8) 0.0015(9) C32 0.0264(11) 0.0210(11) 0.0258(11) -0.0006(9) 0.0076(9) -0.0074(10) C11 0.0221(11) 0.0165(11) 0.0495(14) -0.0025(10) 0.0162(10) -0.0017(10) C64 0.0436(15) 0.0202(12) 0.0444(15) 0.0002(11) 0.0067(12) 0.0017(12) C52 0.0242(11) 0.0287(12) 0.0344(12) -0.0002(10) 0.0116(10) 0.0000(10) C66 0.0415(15) 0.0465(16) 0.0428(15) -0.0024(13) 0.0205(12) -0.0057(13) C19 0.0319(12) 0.0222(11) 0.0223(11) -0.0011(9) 0.0099(9) -0.0059(10) C24 0.0270(12) 0.0335(13) 0.0290(12) 0.0044(10) 0.0053(10) 0.0023(11) C29 0.0372(13) 0.0377(14) 0.0244(11) 0.0054(10) 0.0115(10) -0.0007(12) C31 0.0328(13) 0.0353(14) 0.0269(12) -0.0073(10) 0.0044(10) -0.0013(11) C65 0.0290(12) 0.0235(12) 0.0273(11) -0.0019(9) 0.0053(9) -0.0016(10) C39 0.0164(10) 0.0234(11) 0.0248(11) -0.0003(9) 0.0065(8) 0.0007(9) C62 0.0482(15) 0.0329(14) 0.0303(13) -0.0088(11) 0.0036(11) -0.0022(13) _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 Cl2 C18 1.751(2) . ? Cl5 C51 1.745(2) . ? Cl1 C11 1.748(2) . ? Cl3 C25 1.754(2) . ? Cl6 C58 1.745(2) . ? Cl4 C44 1.743(2) . ? O5 C48 1.367(2) . ? O5 C47 1.442(2) . ? O2 C15 1.377(2) . ? O2 C14 1.440(2) . ? O1 C8 1.375(2) . ? O1 C7 1.427(2) . ? O3 C21 1.444(2) . ? O3 C22 1.376(2) . ? C4 C5 1.413(3) . ? C4 C3 1.398(3) . ? C4 C32 1.510(3) . ? O4 C41 1.376(2) . ? O4 C40 1.440(2) . ? C37 C38 1.404(3) . ? C37 C63 1.520(3) . ? C37 C36 1.400(3) . ? O6 C55 1.371(2) . ? O6 C54 1.437(2) . ? C41 C42 1.376(3) . ? C41 C46 1.389(3) . ? C5 C21 1.512(3) . ? C5 C6 1.400(3) . ? C1 C7 1.507(3) . ? C1 C2 1.401(3) . ? C1 C6 1.412(3) . ? C3 C14 1.508(3) . ? C3 C2 1.402(3) . ? C48 C53 1.389(3) . ? C48 C49 1.383(3) . ? C55 C60 1.378(3) . ? C55 C56 1.391(3) . ? C42 H42 0.9300 . ? C42 C43 1.390(3) . ? C8 C13 1.391(3) . ? C8 C9 1.386(3) . ? C50 H50 0.9300 . ? C50 C51 1.377(3) . ? C50 C49 1.394(3) . ? C13 H13 0.9300 . ? C13 C12 1.396(3) . ? C43 H43 0.9300 . ? C43 C44 1.375(3) . ? C60 H60 0.9300 . ? C60 C59 1.382(3) . ? C15 C16 1.392(3) . ? C15 C20 1.382(3) . ? C38 C54 1.505(3) . ? C38 C39 1.408(3) . ? C53 H53 0.9300 . ? C53 C52 1.381(3) . ? C51 C52 1.377(3) . ? C46 H46 0.9300 . ? C46 C45 1.378(3) . ? C35 C36 1.406(3) . ? C35 C61 1.516(3) . ? C35 C34 1.405(3) . ? C49 H49 0.9300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C63 C64 1.522(3) . ? C56 H56 0.9300 . ? C56 C57 1.377(3) . ? C12 H12 0.9300 . ? C12 C11 1.376(3) . ? C10 H10 0.9300 . ? C10 C9 1.386(3) . ? C10 C11 1.380(3) . ? C22 C23 1.392(3) . ? C22 C27 1.376(3) . ? C58 C57 1.376(3) . ? C58 C59 1.377(3) . ? C16 H16 0.9300 . ? C16 C17 1.374(3) . ? C36 C47 1.507(3) . ? C18 C17 1.381(3) . ? C18 C19 1.369(3) . ? C44 C45 1.380(3) . ? C20 H20 0.9300 . ? C20 C19 1.387(3) . ? C17 H17 0.9300 . ? C9 H9 0.9300 . ? C23 H23 0.9300 . ? C23 C24 1.381(3) . ? C57 H57 0.9300 . ? C25 C26 1.370(3) . ? C25 C24 1.378(3) . ? C59 H59 0.9300 . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C61 H61A 0.9700 . ? C61 H61B 0.9700 . ? C61 C62 1.533(3) . ? C45 H45 0.9300 . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C40 C34 1.513(3) . ? C34 C39 1.408(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C30 C2 1.513(3) . ? C30 C31 1.524(3) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C33 C32 1.522(3) . ? C27 H27 0.9300 . ? C27 C26 1.392(3) . ? C26 H26 0.9300 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C6 1.520(3) . ? C28 C29 1.520(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C64 H64A 0.9600 . ? C64 H64B 0.9600 . ? C64 H64C 0.9600 . ? C52 H52 0.9300 . ? C66 H66A 0.9600 . ? C66 H66B 0.9600 . ? C66 H66C 0.9600 . ? C66 C65 1.518(3) . ? C19 H19 0.9300 . ? C24 H24 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C65 C39 1.527(3) . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 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 C48 O5 C47 119.27(16) . . ? C15 O2 C14 116.90(15) . . ? C8 O1 C7 117.53(15) . . ? C22 O3 C21 116.65(15) . . ? C5 C4 C32 119.91(18) . . ? C3 C4 C5 119.13(18) . . ? C3 C4 C32 120.81(18) . . ? C41 O4 C40 116.64(15) . . ? C38 C37 C63 119.62(19) . . ? C36 C37 C38 119.21(19) . . ? C36 C37 C63 121.18(19) . . ? C55 O6 C54 116.40(15) . . ? O4 C41 C42 124.26(18) . . ? O4 C41 C46 115.86(19) . . ? C42 C41 C46 119.9(2) . . ? C4 C5 C21 118.02(18) . . ? C6 C5 C4 120.17(18) . . ? C6 C5 C21 121.80(18) . . ? C2 C1 C7 120.03(18) . . ? C2 C1 C6 120.37(19) . . ? C6 C1 C7 119.56(18) . . ? C4 C3 C14 118.96(18) . . ? C4 C3 C2 121.32(19) . . ? C2 C3 C14 119.72(18) . . ? O5 C48 C53 115.15(18) . . ? O5 C48 C49 125.13(19) . . ? C49 C48 C53 119.7(2) . . ? O6 C55 C60 124.69(18) . . ? O6 C55 C56 115.35(19) . . ? C60 C55 C56 120.0(2) . . ? C41 C42 H42 120.0 . . ? C41 C42 C43 119.9(2) . . ? C43 C42 H42 120.0 . . ? O1 C8 C13 124.89(19) . . ? O1 C8 C9 115.03(17) . . ? C9 C8 C13 120.09(19) . . ? C51 C50 H50 120.1 . . ? C51 C50 C49 119.8(2) . . ? C49 C50 H50 120.1 . . ? C8 C13 H13 120.4 . . ? C8 C13 C12 119.2(2) . . ? C12 C13 H13 120.4 . . ? C42 C43 H43 120.0 . . ? C44 C43 C42 120.0(2) . . ? C44 C43 H43 120.0 . . ? C55 C60 H60 119.9 . . ? C55 C60 C59 120.12(19) . . ? C59 C60 H60 119.9 . . ? O2 C15 C16 116.02(18) . . ? O2 C15 C20 124.14(19) . . ? C20 C15 C16 119.84(19) . . ? C37 C38 C54 120.17(19) . . ? C37 C38 C39 120.68(19) . . ? C39 C38 C54 119.14(19) . . ? C48 C53 H53 119.6 . . ? C52 C53 C48 120.7(2) . . ? C52 C53 H53 119.6 . . ? C50 C51 Cl5 120.09(17) . . ? C52 C51 Cl5 118.85(17) . . ? C52 C51 C50 121.1(2) . . ? C41 C46 H46 120.0 . . ? C45 C46 C41 120.0(2) . . ? C45 C46 H46 120.0 . . ? C36 C35 C61 119.74(19) . . ? C34 C35 C36 119.32(18) . . ? C34 C35 C61 120.92(19) . . ? C48 C49 C50 119.6(2) . . ? C48 C49 H49 120.2 . . ? C50 C49 H49 120.2 . . ? O3 C21 C5 107.73(15) . . ? O3 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C5 C21 H21A 110.2 . . ? C5 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C37 C63 H63A 108.8 . . ? C37 C63 H63B 108.8 . . ? C37 C63 C64 113.60(18) . . ? H63A C63 H63B 107.7 . . ? C64 C63 H63A 108.8 . . ? C64 C63 H63B 108.8 . . ? C55 C56 H56 120.1 . . ? C57 C56 C55 119.7(2) . . ? C57 C56 H56 120.1 . . ? C13 C12 H12 119.9 . . ? C11 C12 C13 120.1(2) . . ? C11 C12 H12 119.9 . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C11 C10 C9 119.7(2) . . ? O3 C22 C23 116.00(18) . . ? C27 C22 O3 124.51(19) . . ? C27 C22 C23 119.5(2) . . ? C57 C58 Cl6 119.89(17) . . ? C57 C58 C59 120.8(2) . . ? C59 C58 Cl6 119.35(18) . . ? C15 C16 H16 119.8 . . ? C17 C16 C15 120.4(2) . . ? C17 C16 H16 119.8 . . ? C37 C36 C35 120.85(19) . . ? C37 C36 C47 119.21(19) . . ? C35 C36 C47 119.66(18) . . ? C17 C18 Cl2 119.88(17) . . ? C19 C18 Cl2 119.08(17) . . ? C19 C18 C17 121.0(2) . . ? C43 C44 Cl4 119.7(2) . . ? C43 C44 C45 120.2(2) . . ? C45 C44 Cl4 120.12(18) . . ? C15 C20 H20 120.3 . . ? C15 C20 C19 119.5(2) . . ? C19 C20 H20 120.3 . . ? C16 C17 C18 119.2(2) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C8 C9 C10 120.2(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C22 C23 H23 119.8 . . ? C24 C23 C22 120.4(2) . . ? C24 C23 H23 119.8 . . ? C56 C57 H57 120.0 . . ? C58 C57 C56 119.9(2) . . ? C58 C57 H57 120.0 . . ? C26 C25 Cl3 118.81(18) . . ? C26 C25 C24 121.4(2) . . ? C24 C25 Cl3 119.78(17) . . ? C60 C59 H59 120.2 . . ? C58 C59 C60 119.5(2) . . ? C58 C59 H59 120.2 . . ? O5 C47 C36 104.48(16) . . ? O5 C47 H47A 110.9 . . ? O5 C47 H47B 110.9 . . ? C36 C47 H47A 110.9 . . ? C36 C47 H47B 110.9 . . ? H47A C47 H47B 108.9 . . ? O2 C14 C3 106.90(15) . . ? O2 C14 H14A 110.3 . . ? O2 C14 H14B 110.3 . . ? C3 C14 H14A 110.3 . . ? C3 C14 H14B 110.3 . . ? H14A C14 H14B 108.6 . . ? O6 C54 C38 108.67(16) . . ? O6 C54 H54A 110.0 . . ? O6 C54 H54B 110.0 . . ? C38 C54 H54A 110.0 . . ? C38 C54 H54B 110.0 . . ? H54A C54 H54B 108.3 . . ? C35 C61 H61A 109.3 . . ? C35 C61 H61B 109.3 . . ? C35 C61 C62 111.58(18) . . ? H61A C61 H61B 108.0 . . ? C62 C61 H61A 109.3 . . ? C62 C61 H61B 109.3 . . ? C46 C45 C44 120.0(2) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? O4 C40 H40A 110.0 . . ? O4 C40 H40B 110.0 . . ? O4 C40 C34 108.27(16) . . ? H40A C40 H40B 108.4 . . ? C34 C40 H40A 110.0 . . ? C34 C40 H40B 110.0 . . ? C35 C34 C40 120.04(18) . . ? C35 C34 C39 120.44(19) . . ? C39 C34 C40 119.50(19) . . ? O1 C7 C1 108.72(16) . . ? O1 C7 H7A 109.9 . . ? O1 C7 H7B 109.9 . . ? C1 C7 H7A 109.9 . . ? C1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? H30A C30 H30B 107.8 . . ? C2 C30 H30A 109.1 . . ? C2 C30 H30B 109.1 . . ? C2 C30 C31 112.45(17) . . ? C31 C30 H30A 109.1 . . ? C31 C30 H30B 109.1 . . ? C1 C2 C3 119.03(18) . . ? C1 C2 C30 120.86(18) . . ? C3 C2 C30 120.04(18) . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? C22 C27 H27 119.8 . . ? C22 C27 C26 120.4(2) . . ? C26 C27 H27 119.8 . . ? C25 C26 C27 119.2(2) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? H28A C28 H28B 107.9 . . ? C6 C28 H28A 109.2 . . ? C6 C28 H28B 109.2 . . ? C29 C28 H28A 109.2 . . ? C29 C28 H28B 109.2 . . ? C29 C28 C6 112.10(17) . . ? C5 C6 C1 119.73(18) . . ? C5 C6 C28 120.04(18) . . ? C1 C6 C28 120.23(18) . . ? C4 C32 C33 110.96(17) . . ? C4 C32 H32A 109.4 . . ? C4 C32 H32B 109.4 . . ? C33 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C12 C11 Cl1 119.78(17) . . ? C12 C11 C10 120.6(2) . . ? C10 C11 Cl1 119.58(18) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C53 C52 H52 120.4 . . ? C51 C52 C53 119.1(2) . . ? C51 C52 H52 120.4 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C23 C24 H24 120.4 . . ? C25 C24 C23 119.1(2) . . ? C25 C24 H24 120.4 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C66 C65 H65A 109.3 . . ? C66 C65 H65B 109.3 . . ? C66 C65 C39 111.64(18) . . ? H65A C65 H65B 108.0 . . ? C39 C65 H65A 109.3 . . ? C39 C65 H65B 109.3 . . ? C38 C39 C65 119.64(18) . . ? C34 C39 C38 119.13(19) . . ? C34 C39 C65 121.23(19) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C18 C17 C16 -178.81(17) . . . . ? Cl2 C18 C19 C20 178.89(16) . . . . ? Cl5 C51 C52 C53 179.83(17) . . . . ? Cl3 C25 C26 C27 178.71(18) . . . . ? Cl3 C25 C24 C23 -178.17(17) . . . . ? Cl6 C58 C57 C56 178.71(17) . . . . ? Cl6 C58 C59 C60 -178.53(18) . . . . ? Cl4 C44 C45 C46 178.82(18) . . . . ? O5 C48 C53 C52 179.4(2) . . . . ? O5 C48 C49 C50 -179.3(2) . . . . ? O2 C15 C16 C17 179.8(2) . . . . ? O2 C15 C20 C19 -179.74(19) . . . . ? O1 C8 C13 C12 -176.96(19) . . . . ? O1 C8 C9 C10 177.3(2) . . . . ? O3 C22 C23 C24 -179.83(19) . . . . ? O3 C22 C27 C26 -179.6(2) . . . . ? C4 C5 C21 O3 71.7(2) . . . . ? C4 C5 C6 C1 -1.4(3) . . . . ? C4 C5 C6 C28 179.47(17) . . . . ? C4 C3 C14 O2 -82.4(2) . . . . ? C4 C3 C2 C1 -3.6(3) . . . . ? C4 C3 C2 C30 179.49(18) . . . . ? O4 C41 C42 C43 -179.2(2) . . . . ? O4 C41 C46 C45 -179.94(19) . . . . ? O4 C40 C34 C35 71.1(2) . . . . ? O4 C40 C34 C39 -110.8(2) . . . . ? C37 C38 C54 O6 90.9(2) . . . . ? C37 C38 C39 C34 6.6(3) . . . . ? C37 C38 C39 C65 -173.64(18) . . . . ? C37 C36 C47 O5 -84.3(2) . . . . ? O6 C55 C60 C59 178.6(2) . . . . ? O6 C55 C56 C57 -178.50(19) . . . . ? C41 O4 C40 C34 -179.35(17) . . . . ? C41 C42 C43 C44 -0.4(4) . . . . ? C41 C46 C45 C44 -1.2(3) . . . . ? C5 C4 C3 C14 178.54(17) . . . . ? C5 C4 C3 C2 -0.9(3) . . . . ? C5 C4 C32 C33 86.5(2) . . . . ? C3 C4 C5 C21 -177.08(17) . . . . ? C3 C4 C5 C6 3.4(3) . . . . ? C3 C4 C32 C33 -88.9(2) . . . . ? C48 O5 C47 C36 173.69(17) . . . . ? C48 C53 C52 C51 -0.1(3) . . . . ? C55 O6 C54 C38 -174.14(17) . . . . ? C55 C60 C59 C58 -0.2(3) . . . . ? C55 C56 C57 C58 -0.1(3) . . . . ? C42 C41 C46 C45 1.2(3) . . . . ? C42 C43 C44 Cl4 -178.03(18) . . . . ? C42 C43 C44 C45 0.4(4) . . . . ? C8 O1 C7 C1 175.15(17) . . . . ? C8 C13 C12 C11 -1.1(3) . . . . ? C50 C51 C52 C53 0.5(3) . . . . ? C13 C8 C9 C10 -2.7(3) . . . . ? C13 C12 C11 Cl1 177.41(17) . . . . ? C13 C12 C11 C10 -1.1(3) . . . . ? C43 C44 C45 C46 0.4(4) . . . . ? C60 C55 C56 C57 0.5(3) . . . . ? C15 O2 C14 C3 179.86(17) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C15 C20 C19 C18 -0.2(3) . . . . ? C38 C37 C63 C64 89.8(2) . . . . ? C38 C37 C36 C35 -0.6(3) . . . . ? C38 C37 C36 C47 173.28(18) . . . . ? C53 C48 C49 C50 0.4(3) . . . . ? C51 C50 C49 C48 0.0(3) . . . . ? C46 C41 C42 C43 -0.4(3) . . . . ? C35 C36 C47 O5 89.7(2) . . . . ? C35 C34 C39 C38 -2.8(3) . . . . ? C35 C34 C39 C65 177.45(18) . . . . ? C49 C48 C53 C52 -0.3(3) . . . . ? C49 C50 C51 Cl5 -179.77(16) . . . . ? C49 C50 C51 C52 -0.5(3) . . . . ? C21 O3 C22 C23 168.63(19) . . . . ? C21 O3 C22 C27 -11.2(3) . . . . ? C21 C5 C6 C1 179.13(17) . . . . ? C21 C5 C6 C28 0.0(3) . . . . ? C63 C37 C38 C54 -4.2(3) . . . . ? C63 C37 C38 C39 174.82(18) . . . . ? C63 C37 C36 C35 179.67(18) . . . . ? C63 C37 C36 C47 -6.5(3) . . . . ? C56 C55 C60 C59 -0.3(3) . . . . ? C22 O3 C21 C5 -168.36(16) . . . . ? C22 C23 C24 C25 -0.8(3) . . . . ? C22 C27 C26 C25 -0.2(4) . . . . ? C16 C15 C20 C19 1.0(3) . . . . ? C36 C37 C38 C54 175.98(18) . . . . ? C36 C37 C38 C39 -5.0(3) . . . . ? C36 C37 C63 C64 -90.4(2) . . . . ? C36 C35 C61 C62 78.2(2) . . . . ? C36 C35 C34 C40 175.51(18) . . . . ? C36 C35 C34 C39 -2.5(3) . . . . ? C20 C15 C16 C17 -1.0(3) . . . . ? C17 C18 C19 C20 -0.8(3) . . . . ? C9 C8 C13 C12 3.0(3) . . . . ? C9 C10 C11 Cl1 -177.08(18) . . . . ? C9 C10 C11 C12 1.5(4) . . . . ? C23 C22 C27 C26 0.5(3) . . . . ? C57 C58 C59 C60 0.6(4) . . . . ? C59 C58 C57 C56 -0.4(3) . . . . ? C47 O5 C48 C53 -175.12(19) . . . . ? C47 O5 C48 C49 4.5(3) . . . . ? C14 O2 C15 C16 -175.35(18) . . . . ? C14 O2 C15 C20 5.4(3) . . . . ? C14 C3 C2 C1 176.97(18) . . . . ? C14 C3 C2 C30 0.0(3) . . . . ? C54 O6 C55 C60 -10.8(3) . . . . ? C54 O6 C55 C56 168.12(19) . . . . ? C54 C38 C39 C34 -174.29(18) . . . . ? C54 C38 C39 C65 5.4(3) . . . . ? C61 C35 C36 C37 -174.42(18) . . . . ? C61 C35 C36 C47 11.8(3) . . . . ? C61 C35 C34 C40 -5.8(3) . . . . ? C61 C35 C34 C39 176.14(18) . . . . ? C40 O4 C41 C42 -23.3(3) . . . . ? C40 O4 C41 C46 157.90(19) . . . . ? C40 C34 C39 C38 179.10(18) . . . . ? C40 C34 C39 C65 -0.6(3) . . . . ? C34 C35 C36 C37 4.3(3) . . . . ? C34 C35 C36 C47 -169.53(18) . . . . ? C34 C35 C61 C62 -100.5(2) . . . . ? C7 O1 C8 C13 -2.3(3) . . . . ? C7 O1 C8 C9 177.77(18) . . . . ? C7 C1 C2 C3 -172.29(18) . . . . ? C7 C1 C2 C30 4.6(3) . . . . ? C7 C1 C6 C5 174.73(18) . . . . ? C7 C1 C6 C28 -6.1(3) . . . . ? C2 C1 C7 O1 -113.2(2) . . . . ? C2 C1 C6 C5 -3.2(3) . . . . ? C2 C1 C6 C28 175.96(18) . . . . ? C2 C3 C14 O2 97.0(2) . . . . ? C27 C22 C23 C24 0.0(3) . . . . ? C26 C25 C24 C23 1.2(4) . . . . ? C6 C5 C21 O3 -108.8(2) . . . . ? C6 C1 C7 O1 68.9(2) . . . . ? C6 C1 C2 C3 5.6(3) . . . . ? C6 C1 C2 C30 -177.46(18) . . . . ? C32 C4 C5 C21 7.5(3) . . . . ? C32 C4 C5 C6 -172.05(17) . . . . ? C32 C4 C3 C14 -6.1(3) . . . . ? C32 C4 C3 C2 174.50(18) . . . . ? C11 C10 C9 C8 0.4(3) . . . . ? C66 C65 C39 C38 -100.2(2) . . . . ? C66 C65 C39 C34 79.5(3) . . . . ? C19 C18 C17 C16 0.8(3) . . . . ? C24 C25 C26 C27 -0.6(4) . . . . ? C29 C28 C6 C5 77.9(2) . . . . ? C29 C28 C6 C1 -101.3(2) . . . . ? C31 C30 C2 C1 -90.5(2) . . . . ? C31 C30 C2 C3 86.4(2) . . . . ? C39 C38 C54 O6 -88.2(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962406' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-gf-190K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-gf, 190 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Cl3 O3' _chemical_formula_sum 'C33 H33 Cl3 O3' _chemical_formula_weight 583.94 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 19.0913(8) _cell_length_b 13.3962(5) _cell_length_c 24.8034(11) _cell_angle_alpha 90.00 _cell_angle_beta 110.348(5) _cell_angle_gamma 90.00 _cell_volume 5947.6(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 6809 _cell_measurement_temperature 190(2) _cell_measurement_theta_max 29.1040 _cell_measurement_theta_min 3.8307 _exptl_absorpt_coefficient_mu 0.341 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.96615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2448 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_unetI/netI 0.0546 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 29950 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.17 _diffrn_reflns_theta_min 3.84 _diffrn_ambient_temperature 190(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.852 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0089573000 _diffrn_orient_matrix_UB_12 -0.0507489000 _diffrn_orient_matrix_UB_13 0.0025702000 _diffrn_orient_matrix_UB_21 -0.0288751000 _diffrn_orient_matrix_UB_22 0.0025545000 _diffrn_orient_matrix_UB_23 -0.0272601000 _diffrn_orient_matrix_UB_31 0.0255945000 _diffrn_orient_matrix_UB_32 -0.0148672000 _diffrn_orient_matrix_UB_33 -0.0134564000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 9254 _reflns_number_total 13686 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.863 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.057 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 13686 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0554 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+1.4312P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1301 _refine_ls_wR_factor_ref 0.1508 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C63(H63A,H63B), C47(H47A,H47B), C14(H14A,H14B), C54(H54A, H54B), C61(H61A,H61B), C40(H40A,H40B), C7(H7A,H7B), C30(H30A,H30B), C28(H28A, H28B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C42(H42), C50(H50), C13(H13), C43(H43), C60(H60), C53(H53), C46(H46), C49(H49), C56(H56), C12(H12), C10(H10), C16(H16), C20(H20), C17(H17), C9(H9), C23(H23), C57(H57), C59(H59), C45(H45), C27(H27), C26(H26), C52(H52), C19(H19), C24(H24) 2.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C29(H29A,H29B, H29C), C31(H31A,H31B,H31C), C62(H62A,H62B,H62C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl2 Cl 0.45837(4) 0.18349(6) 0.71484(3) 0.04761(18) Uani 1 1 d . . . Cl5 Cl -0.00860(4) 0.15281(6) 0.73544(3) 0.0540(2) Uani 1 1 d . . . Cl1 Cl 1.02496(4) 0.99669(5) 0.59224(4) 0.0590(2) Uani 1 1 d . . . Cl3 Cl 0.65845(4) -0.03520(6) 0.22414(3) 0.0570(2) Uani 1 1 d . . . Cl6 Cl 0.16421(4) -0.05869(7) 0.21491(3) 0.0624(2) Uani 1 1 d . . . Cl4 Cl 0.53485(4) 0.99624(5) 0.60511(5) 0.0784(3) Uani 1 1 d . . . O5 O 0.18949(8) 0.29705(13) 0.61704(7) 0.0369(4) Uani 1 1 d . . . O2 O 0.68211(8) 0.29266(12) 0.61197(6) 0.0323(4) Uani 1 1 d . . . O1 O 0.90197(9) 0.59005(11) 0.55841(7) 0.0353(4) Uani 1 1 d . . . O3 O 0.75993(9) 0.22887(12) 0.42589(7) 0.0338(4) Uani 1 1 d . . . C4 C 0.80100(11) 0.24412(16) 0.55542(9) 0.0242(4) Uani 1 1 d . . . O4 O 0.41751(8) 0.58716(11) 0.57740(7) 0.0347(4) Uani 1 1 d . . . C37 C 0.29037(11) 0.25515(16) 0.54475(10) 0.0276(5) Uani 1 1 d . . . O6 O 0.23345(9) 0.22349(12) 0.40700(7) 0.0371(4) Uani 1 1 d . . . C41 C 0.44205(12) 0.68380(16) 0.58061(9) 0.0274(5) Uani 1 1 d . . . C5 C 0.83874(11) 0.27940(16) 0.51974(9) 0.0252(5) Uani 1 1 d . . . C1 C 0.88170(11) 0.42298(16) 0.58227(9) 0.0264(5) Uani 1 1 d . . . C3 C 0.80119(11) 0.30105(16) 0.60246(9) 0.0243(4) Uani 1 1 d . . . C48 C 0.14786(12) 0.26144(17) 0.64787(10) 0.0290(5) Uani 1 1 d . . . C55 C 0.22178(12) 0.15846(17) 0.36231(10) 0.0292(5) Uani 1 1 d . . . C42 C 0.41438(13) 0.75367(17) 0.53773(10) 0.0343(5) Uani 1 1 d . . . H42 H 0.3753 0.7364 0.5031 0.041 Uiso 1 1 calc . . R C8 C 0.93626(12) 0.68180(16) 0.56883(9) 0.0269(5) Uani 1 1 d . . . C50 C 0.12831(14) 0.18228(18) 0.72838(10) 0.0361(6) Uani 1 1 d . . . H50 H 0.1475 0.1507 0.7649 0.043 Uiso 1 1 calc . . R C13 C 0.99542(12) 0.70710(17) 0.61796(10) 0.0312(5) Uani 1 1 d . . . H13 H 1.0168 0.6585 0.6469 0.037 Uiso 1 1 calc . . R C43 C 0.44394(14) 0.84972(19) 0.54530(12) 0.0424(6) Uani 1 1 d . . . H43 H 0.4252 0.8981 0.5157 0.051 Uiso 1 1 calc . . R C60 C 0.27762(12) 0.10670(18) 0.35081(10) 0.0358(6) Uani 1 1 d . . . H60 H 0.3283 0.1165 0.3743 0.043 Uiso 1 1 calc . . R C15 C 0.63293(11) 0.26540(16) 0.63891(9) 0.0264(5) Uani 1 1 d . . . C38 C 0.30642(12) 0.29354(17) 0.49756(10) 0.0288(5) Uani 1 1 d . . . C53 C 0.07143(13) 0.27367(19) 0.62207(10) 0.0362(6) Uani 1 1 d . . . H53 H 0.0518 0.3054 0.5856 0.043 Uiso 1 1 calc . . R C51 C 0.05236(14) 0.19483(17) 0.70177(10) 0.0340(5) Uani 1 1 d . . . C46 C 0.49988(13) 0.70960(19) 0.63100(10) 0.0352(5) Uani 1 1 d . . . H46 H 0.5197 0.6611 0.6603 0.042 Uiso 1 1 calc . . R C35 C 0.31504(11) 0.41963(16) 0.59000(9) 0.0265(5) Uani 1 1 d . . . C49 C 0.17685(13) 0.21629(17) 0.70130(10) 0.0314(5) Uani 1 1 d . . . H49 H 0.2293 0.2085 0.7194 0.038 Uiso 1 1 calc . . R C21 C 0.83459(12) 0.21862(17) 0.46736(10) 0.0311(5) Uani 1 1 d . . . H21A H 0.8717 0.2432 0.4509 0.037 Uiso 1 1 calc . . R H21B H 0.8455 0.1476 0.4780 0.037 Uiso 1 1 calc . . R C63 C 0.26796(13) 0.14624(17) 0.54504(10) 0.0338(5) Uani 1 1 d . . . H63A H 0.2408 0.1247 0.5050 0.041 Uiso 1 1 calc . . R H63B H 0.2333 0.1401 0.5667 0.041 Uiso 1 1 calc . . R C56 C 0.14787(13) 0.14372(18) 0.32753(10) 0.0351(5) Uani 1 1 d . . . H56 H 0.1092 0.1794 0.3350 0.042 Uiso 1 1 calc . . R C12 C 1.02339(12) 0.80416(18) 0.62474(10) 0.0341(5) Uani 1 1 d . . . H12 H 1.0636 0.8221 0.6585 0.041 Uiso 1 1 calc . . R C10 C 0.93522(13) 0.84792(18) 0.53240(12) 0.0400(6) Uani 1 1 d . . . H10 H 0.9153 0.8959 0.5028 0.048 Uiso 1 1 calc . . R C22 C 0.74013(12) 0.16484(17) 0.37967(9) 0.0289(5) Uani 1 1 d . . . C58 C 0.18639(14) 0.02662(19) 0.27155(10) 0.0366(6) Uani 1 1 d . . . C16 C 0.55819(12) 0.28721(19) 0.60900(10) 0.0341(5) Uani 1 1 d . . . H16 H 0.5441 0.3189 0.5725 0.041 Uiso 1 1 calc . . R C36 C 0.29442(11) 0.31890(16) 0.59065(9) 0.0262(5) Uani 1 1 d . . . C18 C 0.52573(13) 0.21701(17) 0.68522(10) 0.0310(5) Uani 1 1 d . . . C44 C 0.50024(13) 0.87467(18) 0.59555(13) 0.0432(6) Uani 1 1 d . . . C20 C 0.65360(12) 0.22014(17) 0.69214(9) 0.0298(5) Uani 1 1 d . . . H20 H 0.7046 0.2056 0.7128 0.036 Uiso 1 1 calc . . R C17 C 0.50467(13) 0.26291(19) 0.63223(10) 0.0352(6) Uani 1 1 d . . . H17 H 0.4536 0.2776 0.6119 0.042 Uiso 1 1 calc . . R C9 C 0.90710(12) 0.75171(17) 0.52577(10) 0.0341(5) Uani 1 1 d . . . H9 H 0.8676 0.7336 0.4915 0.041 Uiso 1 1 calc . . R C23 C 0.66462(13) 0.16284(19) 0.34629(10) 0.0365(6) Uani 1 1 d . . . H23 H 0.6304 0.2042 0.3561 0.044 Uiso 1 1 calc . . R C57 C 0.13036(13) 0.07782(19) 0.28235(10) 0.0386(6) Uani 1 1 d . . . H57 H 0.0797 0.0677 0.2587 0.046 Uiso 1 1 calc . . R C25 C 0.68942(14) 0.04177(19) 0.28488(10) 0.0372(6) Uani 1 1 d . . . C59 C 0.25994(13) 0.0406(2) 0.30516(11) 0.0393(6) Uani 1 1 d . . . H59 H 0.2983 0.0052 0.2971 0.047 Uiso 1 1 calc . . R C47 C 0.26902(12) 0.28065(18) 0.63807(10) 0.0312(5) Uani 1 1 d . . . H47A H 0.2807 0.2088 0.6452 0.037 Uiso 1 1 calc . . R H47B H 0.2934 0.3180 0.6742 0.037 Uiso 1 1 calc . . R C14 C 0.75894(11) 0.26412(18) 0.64005(9) 0.0281(5) Uani 1 1 d . . . H14A H 0.7632 0.1907 0.6443 0.034 Uiso 1 1 calc . . R H14B H 0.7792 0.2948 0.6787 0.034 Uiso 1 1 calc . . R C54 C 0.30683(13) 0.22504(18) 0.44952(10) 0.0332(5) Uani 1 1 d . . . H54A H 0.3433 0.2491 0.4323 0.040 Uiso 1 1 calc . . R H54B H 0.3215 0.1569 0.4646 0.040 Uiso 1 1 calc . . R C61 C 0.32580(14) 0.48397(18) 0.64246(10) 0.0363(6) Uani 1 1 d . . . H61A H 0.2853 0.4701 0.6577 0.044 Uiso 1 1 calc . . R H61B H 0.3226 0.5552 0.6313 0.044 Uiso 1 1 calc . . R C45 C 0.52845(13) 0.8048(2) 0.63849(11) 0.0420(6) Uani 1 1 d . . . H45 H 0.5675 0.8225 0.6731 0.050 Uiso 1 1 calc . . R C40 C 0.34309(12) 0.56775(17) 0.53784(10) 0.0317(5) Uani 1 1 d . . . H40A H 0.3396 0.5856 0.4982 0.038 Uiso 1 1 calc . . R H40B H 0.3064 0.6084 0.5482 0.038 Uiso 1 1 calc . . R C34 C 0.32659(12) 0.45757(16) 0.54100(10) 0.0278(5) Uani 1 1 d . . . C7 C 0.93115(12) 0.51390(17) 0.60000(10) 0.0306(5) Uani 1 1 d . . . H7A H 0.9326 0.5373 0.6382 0.037 Uiso 1 1 calc . . R H7B H 0.9827 0.4970 0.6026 0.037 Uiso 1 1 calc . . R C30 C 0.83832(12) 0.45305(18) 0.66685(10) 0.0317(5) Uani 1 1 d . . . H30A H 0.7890 0.4451 0.6712 0.038 Uiso 1 1 calc . . R H30B H 0.8448 0.5245 0.6596 0.038 Uiso 1 1 calc . . R C2 C 0.83977(11) 0.39219(16) 0.61557(9) 0.0251(5) Uani 1 1 d . . . C33 C 0.82132(16) 0.06163(18) 0.57594(12) 0.0452(7) Uani 1 1 d . . . H33A H 0.8645 0.0643 0.5632 0.068 Uiso 1 1 calc . . GR H33B H 0.7977 -0.0042 0.5671 0.068 Uiso 1 1 calc . . GR H33C H 0.8379 0.0731 0.6175 0.068 Uiso 1 1 calc . . GR C27 C 0.78937(13) 0.10415(19) 0.36559(11) 0.0390(6) Uani 1 1 d . . . H27 H 0.8409 0.1046 0.3886 0.047 Uiso 1 1 calc . . R C26 C 0.76405(14) 0.0424(2) 0.31786(11) 0.0424(6) Uani 1 1 d . . . H26 H 0.7981 0.0007 0.3080 0.051 Uiso 1 1 calc . . R C28 C 0.92162(12) 0.40564(18) 0.49510(9) 0.0309(5) Uani 1 1 d . . . H28A H 0.9471 0.3488 0.4843 0.037 Uiso 1 1 calc . . R H28B H 0.9603 0.4541 0.5168 0.037 Uiso 1 1 calc . . R C6 C 0.88018(11) 0.36823(16) 0.53352(9) 0.0257(5) Uani 1 1 d . . . C32 C 0.76506(12) 0.14203(16) 0.54484(10) 0.0309(5) Uani 1 1 d . . . H32A H 0.7459 0.1280 0.5030 0.037 Uiso 1 1 calc . . R H32B H 0.7223 0.1408 0.5587 0.037 Uiso 1 1 calc . . R C11 C 0.99285(13) 0.87371(17) 0.58265(12) 0.0359(6) Uani 1 1 d . . . C64 C 0.33453(15) 0.07676(19) 0.57180(13) 0.0473(7) Uani 1 1 d . . . H64A H 0.3597 0.0947 0.6123 0.071 Uiso 1 1 calc . . GR H64B H 0.3696 0.0835 0.5511 0.071 Uiso 1 1 calc . . GR H64C H 0.3170 0.0076 0.5692 0.071 Uiso 1 1 calc . . GR C52 C 0.02333(13) 0.24007(18) 0.64892(11) 0.0366(6) Uani 1 1 d . . . H52 H -0.0291 0.2482 0.6310 0.044 Uiso 1 1 calc . . R C66 C 0.41093(15) 0.4507(2) 0.44655(13) 0.0526(7) Uani 1 1 d . . . H66A H 0.4367 0.3864 0.4557 0.079 Uiso 1 1 calc . . GR H66B H 0.4340 0.4980 0.4779 0.079 Uiso 1 1 calc . . GR H66C H 0.4148 0.4768 0.4108 0.079 Uiso 1 1 calc . . GR C19 C 0.59926(13) 0.19603(17) 0.71525(10) 0.0311(5) Uani 1 1 d . . . H19 H 0.6130 0.1650 0.7519 0.037 Uiso 1 1 calc . . R C24 C 0.63917(13) 0.10080(19) 0.29889(10) 0.0382(6) Uani 1 1 d . . . H24 H 0.5876 0.0989 0.2762 0.046 Uiso 1 1 calc . . R C29 C 0.86945(14) 0.4554(2) 0.44076(10) 0.0404(6) Uani 1 1 d . . . H29A H 0.8983 0.4779 0.4172 0.061 Uiso 1 1 calc . . GR H29B H 0.8451 0.5128 0.4512 0.061 Uiso 1 1 calc . . GR H29C H 0.8314 0.4074 0.4189 0.061 Uiso 1 1 calc . . GR C31 C 0.89940(14) 0.4214(2) 0.72264(10) 0.0411(6) Uani 1 1 d . . . H31A H 0.9484 0.4297 0.7187 0.062 Uiso 1 1 calc . . GR H31B H 0.8923 0.3513 0.7306 0.062 Uiso 1 1 calc . . GR H31C H 0.8968 0.4631 0.7544 0.062 Uiso 1 1 calc . . GR C65 C 0.32949(13) 0.43695(19) 0.43923(10) 0.0370(6) Uani 1 1 d . . . H65A H 0.3061 0.3904 0.4070 0.044 Uiso 1 1 calc . . R H65B H 0.3034 0.5019 0.4294 0.044 Uiso 1 1 calc . . R C39 C 0.32028(12) 0.39596(17) 0.49377(10) 0.0299(5) Uani 1 1 d . . . C62 C 0.40152(16) 0.4641(2) 0.68957(11) 0.0486(7) Uani 1 1 d . . . H62A H 0.4058 0.5046 0.7235 0.073 Uiso 1 1 calc . . GR H62B H 0.4418 0.4818 0.6753 0.073 Uiso 1 1 calc . . GR H62C H 0.4054 0.3933 0.7000 0.073 Uiso 1 1 calc . . GR 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 Cl2 0.0435(3) 0.0634(5) 0.0475(4) 0.0036(3) 0.0304(3) -0.0069(3) Cl5 0.0637(4) 0.0536(4) 0.0628(5) 0.0111(4) 0.0448(4) 0.0010(4) Cl1 0.0389(3) 0.0228(3) 0.1082(6) -0.0034(4) 0.0166(4) -0.0061(3) Cl3 0.0601(4) 0.0617(5) 0.0432(4) -0.0216(3) 0.0105(3) -0.0119(4) Cl6 0.0613(4) 0.0768(6) 0.0420(4) -0.0276(4) 0.0089(3) -0.0160(4) Cl4 0.0390(4) 0.0286(4) 0.1474(9) -0.0164(5) 0.0067(4) -0.0071(3) O5 0.0251(8) 0.0519(11) 0.0359(9) 0.0150(8) 0.0135(7) 0.0038(7) O2 0.0211(7) 0.0467(10) 0.0315(8) 0.0110(7) 0.0121(6) -0.0001(7) O1 0.0405(9) 0.0228(8) 0.0367(9) 0.0023(7) 0.0060(7) -0.0060(7) O3 0.0366(9) 0.0330(9) 0.0312(8) -0.0067(7) 0.0109(7) 0.0072(7) C4 0.0215(10) 0.0212(11) 0.0282(11) 0.0011(9) 0.0063(8) -0.0013(8) O4 0.0323(8) 0.0242(9) 0.0419(9) 0.0027(7) 0.0058(7) -0.0016(7) C37 0.0224(10) 0.0231(12) 0.0363(12) -0.0010(10) 0.0089(9) -0.0019(9) O6 0.0326(8) 0.0366(10) 0.0407(9) -0.0116(8) 0.0112(7) 0.0045(7) C41 0.0262(10) 0.0231(12) 0.0340(12) -0.0052(9) 0.0120(9) -0.0009(9) C5 0.0247(10) 0.0243(11) 0.0272(11) 0.0005(9) 0.0097(8) 0.0024(9) C1 0.0247(10) 0.0248(12) 0.0286(11) 0.0016(9) 0.0077(9) -0.0023(9) C3 0.0188(9) 0.0269(12) 0.0265(11) 0.0018(9) 0.0071(8) -0.0014(9) C48 0.0315(11) 0.0272(12) 0.0311(12) 0.0013(10) 0.0146(9) 0.0008(10) C55 0.0312(11) 0.0254(12) 0.0320(12) -0.0022(10) 0.0120(9) -0.0018(9) C42 0.0330(12) 0.0273(13) 0.0371(13) 0.0004(10) 0.0053(10) -0.0010(10) C8 0.0273(10) 0.0218(11) 0.0338(12) -0.0012(9) 0.0134(9) -0.0031(9) C50 0.0495(14) 0.0313(13) 0.0296(12) 0.0036(10) 0.0165(11) 0.0010(11) C13 0.0325(12) 0.0305(13) 0.0314(12) 0.0024(10) 0.0121(9) -0.0024(10) C43 0.0363(13) 0.0253(13) 0.0604(17) 0.0036(12) 0.0102(12) -0.0003(11) C60 0.0243(11) 0.0403(14) 0.0415(14) -0.0128(11) 0.0099(10) -0.0048(10) C15 0.0259(10) 0.0264(12) 0.0299(11) -0.0018(9) 0.0134(9) -0.0041(9) C38 0.0262(10) 0.0264(12) 0.0341(12) -0.0058(10) 0.0110(9) -0.0002(9) C53 0.0315(12) 0.0435(15) 0.0343(13) 0.0106(11) 0.0124(10) 0.0059(11) C51 0.0442(13) 0.0273(13) 0.0388(13) -0.0032(10) 0.0249(11) -0.0026(11) C46 0.0328(12) 0.0367(14) 0.0326(12) -0.0027(11) 0.0069(10) 0.0025(11) C35 0.0219(10) 0.0260(12) 0.0320(11) -0.0039(9) 0.0098(9) 0.0029(9) C49 0.0332(12) 0.0286(13) 0.0308(12) -0.0001(10) 0.0091(9) 0.0021(10) C21 0.0313(11) 0.0290(13) 0.0336(12) -0.0042(10) 0.0122(9) 0.0019(10) C63 0.0339(12) 0.0244(12) 0.0394(13) -0.0023(10) 0.0082(10) -0.0063(10) C56 0.0287(11) 0.0355(14) 0.0398(13) 0.0065(11) 0.0101(10) 0.0035(10) C12 0.0302(11) 0.0320(13) 0.0399(13) -0.0085(11) 0.0120(10) -0.0084(10) C10 0.0314(12) 0.0257(13) 0.0588(16) 0.0084(12) 0.0104(11) 0.0015(10) C22 0.0348(11) 0.0251(12) 0.0288(11) 0.0015(9) 0.0136(9) 0.0015(10) C58 0.0409(13) 0.0396(15) 0.0259(12) -0.0049(10) 0.0074(10) -0.0100(11) C16 0.0286(11) 0.0423(15) 0.0327(12) 0.0068(11) 0.0124(9) 0.0011(10) C36 0.0206(9) 0.0276(12) 0.0300(11) -0.0003(9) 0.0083(8) 0.0003(9) C18 0.0347(12) 0.0304(13) 0.0356(12) -0.0063(10) 0.0220(10) -0.0074(10) C44 0.0288(12) 0.0237(13) 0.0746(19) -0.0116(13) 0.0146(12) -0.0028(10) C20 0.0303(11) 0.0298(13) 0.0292(11) 0.0038(10) 0.0105(9) -0.0013(10) C17 0.0262(11) 0.0432(15) 0.0387(13) 0.0026(11) 0.0144(10) 0.0007(10) C9 0.0280(11) 0.0295(13) 0.0399(13) 0.0023(11) 0.0057(10) -0.0028(10) C23 0.0374(13) 0.0404(15) 0.0325(12) 0.0027(11) 0.0130(10) 0.0107(11) C57 0.0305(12) 0.0424(15) 0.0359(13) 0.0066(11) 0.0025(10) -0.0055(11) C25 0.0443(14) 0.0328(14) 0.0330(12) -0.0061(11) 0.0116(11) -0.0080(11) C59 0.0327(12) 0.0453(15) 0.0421(14) -0.0141(12) 0.0158(11) -0.0029(11) C47 0.0237(10) 0.0349(13) 0.0333(12) 0.0005(10) 0.0078(9) 0.0009(10) C14 0.0211(10) 0.0358(13) 0.0260(11) 0.0031(10) 0.0064(8) -0.0005(9) C54 0.0334(12) 0.0285(13) 0.0391(13) -0.0088(10) 0.0144(10) -0.0034(10) C61 0.0459(14) 0.0274(13) 0.0381(13) -0.0059(10) 0.0177(11) 0.0042(11) C45 0.0285(12) 0.0428(16) 0.0475(15) -0.0170(13) 0.0040(11) -0.0010(11) C40 0.0311(11) 0.0246(12) 0.0355(12) -0.0031(10) 0.0067(10) -0.0037(10) C34 0.0262(10) 0.0215(11) 0.0351(12) -0.0033(9) 0.0099(9) 0.0004(9) C7 0.0316(11) 0.0293(13) 0.0300(12) 0.0029(10) 0.0095(9) -0.0036(10) C30 0.0304(11) 0.0328(13) 0.0337(12) -0.0052(10) 0.0135(10) 0.0003(10) C2 0.0230(10) 0.0256(12) 0.0269(11) -0.0021(9) 0.0090(8) -0.0005(9) C33 0.0589(17) 0.0227(13) 0.0507(16) 0.0037(12) 0.0147(13) 0.0005(12) C27 0.0315(12) 0.0411(15) 0.0471(15) -0.0139(12) 0.0172(11) -0.0021(11) C26 0.0376(13) 0.0441(16) 0.0494(15) -0.0194(13) 0.0203(12) -0.0043(12) C28 0.0289(11) 0.0351(13) 0.0320(12) 0.0012(10) 0.0149(9) -0.0021(10) C6 0.0225(10) 0.0275(12) 0.0275(11) 0.0035(9) 0.0094(8) 0.0017(9) C32 0.0319(11) 0.0258(12) 0.0342(12) -0.0009(10) 0.0106(10) -0.0081(10) C11 0.0290(11) 0.0214(12) 0.0607(16) -0.0038(11) 0.0200(11) -0.0027(10) C64 0.0523(16) 0.0259(14) 0.0562(17) 0.0014(12) 0.0092(13) 0.0034(12) C52 0.0335(12) 0.0362(14) 0.0441(14) 0.0021(11) 0.0185(11) 0.0010(11) C66 0.0500(16) 0.0606(19) 0.0541(17) -0.0011(15) 0.0269(14) -0.0065(14) C19 0.0386(12) 0.0290(13) 0.0283(11) -0.0002(10) 0.0148(10) -0.0044(10) C24 0.0340(12) 0.0409(15) 0.0350(13) 0.0039(11) 0.0059(10) 0.0038(11) C29 0.0443(14) 0.0477(16) 0.0308(13) 0.0084(11) 0.0151(11) 0.0010(12) C31 0.0411(13) 0.0444(16) 0.0323(13) -0.0077(11) 0.0059(11) -0.0012(12) C65 0.0383(13) 0.0332(14) 0.0370(13) -0.0029(11) 0.0098(10) -0.0001(11) C39 0.0265(11) 0.0292(12) 0.0345(12) -0.0003(10) 0.0112(9) -0.0004(10) C62 0.0538(16) 0.0407(16) 0.0414(15) -0.0110(12) 0.0041(12) -0.0015(13) _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 Cl2 C18 1.747(2) . ? Cl5 C51 1.745(2) . ? Cl1 C11 1.745(2) . ? Cl3 C25 1.750(2) . ? Cl6 C58 1.745(2) . ? Cl4 C44 1.742(3) . ? O5 C48 1.366(3) . ? O5 C47 1.440(2) . ? O2 C15 1.378(2) . ? O2 C14 1.439(2) . ? O1 C8 1.374(3) . ? O1 C7 1.420(3) . ? O3 C21 1.445(3) . ? O3 C22 1.375(3) . ? C4 C5 1.403(3) . ? C4 C3 1.393(3) . ? C4 C32 1.512(3) . ? O4 C41 1.370(3) . ? O4 C40 1.442(3) . ? C37 C38 1.407(3) . ? C37 C63 1.521(3) . ? C37 C36 1.404(3) . ? O6 C55 1.366(3) . ? O6 C54 1.431(3) . ? C41 C42 1.377(3) . ? C41 C46 1.393(3) . ? C5 C21 1.512(3) . ? C5 C6 1.404(3) . ? C1 C7 1.510(3) . ? C1 C2 1.398(3) . ? C1 C6 1.406(3) . ? C3 C14 1.512(3) . ? C3 C2 1.404(3) . ? C48 C53 1.384(3) . ? C48 C49 1.385(3) . ? C55 C60 1.382(3) . ? C55 C56 1.388(3) . ? C42 H42 0.9500 . ? C42 C43 1.391(3) . ? C8 C13 1.385(3) . ? C8 C9 1.384(3) . ? C50 H50 0.9500 . ? C50 C51 1.379(3) . ? C50 C49 1.397(3) . ? C13 H13 0.9500 . ? C13 C12 1.393(3) . ? C43 H43 0.9500 . ? C43 C44 1.374(4) . ? C60 H60 0.9500 . ? C60 C59 1.383(3) . ? C15 C16 1.391(3) . ? C15 C20 1.380(3) . ? C38 C54 1.506(3) . ? C38 C39 1.407(3) . ? C53 H53 0.9500 . ? C53 C52 1.384(3) . ? C51 C52 1.374(3) . ? C46 H46 0.9500 . ? C46 C45 1.375(3) . ? C35 C36 1.407(3) . ? C35 C61 1.514(3) . ? C35 C34 1.404(3) . ? C49 H49 0.9500 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C63 C64 1.528(3) . ? C56 H56 0.9500 . ? C56 C57 1.373(3) . ? C12 H12 0.9500 . ? C12 C11 1.369(3) . ? C10 H10 0.9500 . ? C10 C9 1.384(3) . ? C10 C11 1.389(4) . ? C22 C23 1.391(3) . ? C22 C27 1.377(3) . ? C58 C57 1.373(3) . ? C58 C59 1.374(3) . ? C16 H16 0.9500 . ? C16 C17 1.375(3) . ? C36 C47 1.509(3) . ? C18 C17 1.378(3) . ? C18 C19 1.370(3) . ? C44 C45 1.378(4) . ? C20 H20 0.9500 . ? C20 C19 1.387(3) . ? C17 H17 0.9500 . ? C9 H9 0.9500 . ? C23 H23 0.9500 . ? C23 C24 1.383(3) . ? C57 H57 0.9500 . ? C25 C26 1.374(3) . ? C25 C24 1.378(3) . ? C59 H59 0.9500 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C61 C62 1.533(3) . ? C45 H45 0.9500 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C40 C34 1.517(3) . ? C34 C39 1.404(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 C2 1.519(3) . ? C30 C31 1.527(3) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C33 C32 1.527(3) . ? C27 H27 0.9500 . ? C27 C26 1.386(3) . ? C26 H26 0.9500 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C6 1.520(3) . ? C28 C29 1.523(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C52 H52 0.9500 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C66 C65 1.513(3) . ? C19 H19 0.9500 . ? C24 H24 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C65 C39 1.526(3) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? 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 C48 O5 C47 119.29(17) . . ? C15 O2 C14 116.53(16) . . ? C8 O1 C7 117.72(17) . . ? C22 O3 C21 116.82(16) . . ? C5 C4 C32 119.79(19) . . ? C3 C4 C5 119.45(19) . . ? C3 C4 C32 120.64(19) . . ? C41 O4 C40 116.50(17) . . ? C38 C37 C63 119.8(2) . . ? C36 C37 C38 119.1(2) . . ? C36 C37 C63 121.1(2) . . ? C55 O6 C54 116.68(17) . . ? O4 C41 C42 124.5(2) . . ? O4 C41 C46 115.8(2) . . ? C42 C41 C46 119.7(2) . . ? C4 C5 C21 118.40(19) . . ? C4 C5 C6 120.08(19) . . ? C6 C5 C21 121.50(19) . . ? C2 C1 C7 119.6(2) . . ? C2 C1 C6 120.63(19) . . ? C6 C1 C7 119.69(19) . . ? C4 C3 C14 119.39(19) . . ? C4 C3 C2 121.22(19) . . ? C2 C3 C14 119.40(19) . . ? O5 C48 C53 115.1(2) . . ? O5 C48 C49 124.8(2) . . ? C53 C48 C49 120.0(2) . . ? O6 C55 C60 124.6(2) . . ? O6 C55 C56 116.0(2) . . ? C60 C55 C56 119.4(2) . . ? C41 C42 H42 120.1 . . ? C41 C42 C43 119.7(2) . . ? C43 C42 H42 120.1 . . ? O1 C8 C13 125.0(2) . . ? O1 C8 C9 115.01(19) . . ? C9 C8 C13 120.0(2) . . ? C51 C50 H50 120.2 . . ? C51 C50 C49 119.5(2) . . ? C49 C50 H50 120.2 . . ? C8 C13 H13 120.1 . . ? C8 C13 C12 119.7(2) . . ? C12 C13 H13 120.1 . . ? C42 C43 H43 120.0 . . ? C44 C43 C42 120.0(2) . . ? C44 C43 H43 120.0 . . ? C55 C60 H60 119.9 . . ? C55 C60 C59 120.2(2) . . ? C59 C60 H60 119.9 . . ? O2 C15 C16 115.56(19) . . ? O2 C15 C20 124.35(19) . . ? C20 C15 C16 120.09(19) . . ? C37 C38 C54 119.9(2) . . ? C37 C38 C39 120.8(2) . . ? C39 C38 C54 119.3(2) . . ? C48 C53 H53 119.7 . . ? C52 C53 C48 120.5(2) . . ? C52 C53 H53 119.7 . . ? C50 C51 Cl5 119.79(19) . . ? C52 C51 Cl5 118.96(19) . . ? C52 C51 C50 121.3(2) . . ? C41 C46 H46 119.8 . . ? C45 C46 C41 120.3(2) . . ? C45 C46 H46 119.8 . . ? C36 C35 C61 119.4(2) . . ? C34 C35 C36 119.07(19) . . ? C34 C35 C61 121.5(2) . . ? C48 C49 C50 119.4(2) . . ? C48 C49 H49 120.3 . . ? C50 C49 H49 120.3 . . ? O3 C21 C5 107.72(16) . . ? O3 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C5 C21 H21A 110.2 . . ? C5 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C37 C63 H63A 108.9 . . ? C37 C63 H63B 108.9 . . ? C37 C63 C64 113.17(19) . . ? H63A C63 H63B 107.8 . . ? C64 C63 H63A 108.9 . . ? C64 C63 H63B 108.9 . . ? C55 C56 H56 119.8 . . ? C57 C56 C55 120.3(2) . . ? C57 C56 H56 119.8 . . ? C13 C12 H12 120.0 . . ? C11 C12 C13 119.9(2) . . ? C11 C12 H12 120.0 . . ? C9 C10 H10 120.3 . . ? C9 C10 C11 119.4(2) . . ? C11 C10 H10 120.3 . . ? O3 C22 C23 115.84(19) . . ? O3 C22 C27 124.5(2) . . ? C27 C22 C23 119.7(2) . . ? C57 C58 Cl6 119.78(18) . . ? C57 C58 C59 121.0(2) . . ? C59 C58 Cl6 119.2(2) . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.0(2) . . ? C17 C16 H16 120.0 . . ? C37 C36 C35 120.7(2) . . ? C37 C36 C47 118.9(2) . . ? C35 C36 C47 120.10(19) . . ? C17 C18 Cl2 120.15(18) . . ? C19 C18 Cl2 118.92(18) . . ? C19 C18 C17 120.9(2) . . ? C43 C44 Cl4 119.4(2) . . ? C43 C44 C45 120.5(2) . . ? C45 C44 Cl4 120.1(2) . . ? C15 C20 H20 120.3 . . ? C15 C20 C19 119.5(2) . . ? C19 C20 H20 120.3 . . ? C16 C17 C18 119.5(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C8 C9 C10 120.2(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C22 C23 H23 119.9 . . ? C24 C23 C22 120.2(2) . . ? C24 C23 H23 119.9 . . ? C56 C57 H57 120.2 . . ? C58 C57 C56 119.7(2) . . ? C58 C57 H57 120.2 . . ? C26 C25 Cl3 119.07(19) . . ? C26 C25 C24 121.0(2) . . ? C24 C25 Cl3 119.92(19) . . ? C60 C59 H59 120.3 . . ? C58 C59 C60 119.4(2) . . ? C58 C59 H59 120.3 . . ? O5 C47 C36 104.47(17) . . ? O5 C47 H47A 110.9 . . ? O5 C47 H47B 110.9 . . ? C36 C47 H47A 110.9 . . ? C36 C47 H47B 110.9 . . ? H47A C47 H47B 108.9 . . ? O2 C14 C3 106.68(16) . . ? O2 C14 H14A 110.4 . . ? O2 C14 H14B 110.4 . . ? C3 C14 H14A 110.4 . . ? C3 C14 H14B 110.4 . . ? H14A C14 H14B 108.6 . . ? O6 C54 C38 108.60(18) . . ? O6 C54 H54A 110.0 . . ? O6 C54 H54B 110.0 . . ? C38 C54 H54A 110.0 . . ? C38 C54 H54B 110.0 . . ? H54A C54 H54B 108.4 . . ? C35 C61 H61A 109.3 . . ? C35 C61 H61B 109.3 . . ? C35 C61 C62 111.51(19) . . ? H61A C61 H61B 108.0 . . ? C62 C61 H61A 109.3 . . ? C62 C61 H61B 109.3 . . ? C46 C45 C44 119.7(2) . . ? C46 C45 H45 120.2 . . ? C44 C45 H45 120.2 . . ? O4 C40 H40A 110.0 . . ? O4 C40 H40B 110.0 . . ? O4 C40 C34 108.27(17) . . ? H40A C40 H40B 108.4 . . ? C34 C40 H40A 110.0 . . ? C34 C40 H40B 110.0 . . ? C35 C34 C40 119.67(19) . . ? C39 C34 C35 121.1(2) . . ? C39 C34 C40 119.2(2) . . ? O1 C7 C1 108.69(17) . . ? O1 C7 H7A 110.0 . . ? O1 C7 H7B 110.0 . . ? C1 C7 H7A 110.0 . . ? C1 C7 H7B 110.0 . . ? H7A C7 H7B 108.3 . . ? H30A C30 H30B 107.9 . . ? C2 C30 H30A 109.1 . . ? C2 C30 H30B 109.1 . . ? C2 C30 C31 112.29(19) . . ? C31 C30 H30A 109.1 . . ? C31 C30 H30B 109.1 . . ? C1 C2 C3 118.81(19) . . ? C1 C2 C30 121.16(19) . . ? C3 C2 C30 119.98(19) . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? C22 C27 H27 119.9 . . ? C22 C27 C26 120.2(2) . . ? C26 C27 H27 119.9 . . ? C25 C26 C27 119.6(2) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? H28A C28 H28B 107.9 . . ? C6 C28 H28A 109.2 . . ? C6 C28 H28B 109.2 . . ? C6 C28 C29 112.11(18) . . ? C29 C28 H28A 109.2 . . ? C29 C28 H28B 109.2 . . ? C5 C6 C1 119.55(19) . . ? C5 C6 C28 119.93(19) . . ? C1 C6 C28 120.51(19) . . ? C4 C32 C33 110.69(19) . . ? C4 C32 H32A 109.5 . . ? C4 C32 H32B 109.5 . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? C12 C11 Cl1 120.15(19) . . ? C12 C11 C10 120.6(2) . . ? C10 C11 Cl1 119.2(2) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C53 C52 H52 120.4 . . ? C51 C52 C53 119.2(2) . . ? C51 C52 H52 120.4 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C23 C24 H24 120.3 . . ? C25 C24 C23 119.3(2) . . ? C25 C24 H24 120.3 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C66 C65 H65A 109.3 . . ? C66 C65 H65B 109.3 . . ? C66 C65 C39 111.6(2) . . ? H65A C65 H65B 108.0 . . ? C39 C65 H65A 109.3 . . ? C39 C65 H65B 109.3 . . ? C38 C39 C65 119.5(2) . . ? C34 C39 C38 118.8(2) . . ? C34 C39 C65 121.7(2) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C18 C17 C16 -178.81(19) . . . . ? Cl2 C18 C19 C20 178.74(17) . . . . ? Cl5 C51 C52 C53 179.90(19) . . . . ? Cl3 C25 C26 C27 179.1(2) . . . . ? Cl3 C25 C24 C23 -178.63(19) . . . . ? Cl6 C58 C57 C56 178.94(19) . . . . ? Cl6 C58 C59 C60 -178.7(2) . . . . ? Cl4 C44 C45 C46 178.82(19) . . . . ? O5 C48 C53 C52 179.6(2) . . . . ? O5 C48 C49 C50 -179.6(2) . . . . ? O2 C15 C16 C17 180.0(2) . . . . ? O2 C15 C20 C19 179.9(2) . . . . ? O1 C8 C13 C12 -177.1(2) . . . . ? O1 C8 C9 C10 177.5(2) . . . . ? O3 C22 C23 C24 -180.0(2) . . . . ? O3 C22 C27 C26 -179.7(2) . . . . ? C4 C5 C21 O3 72.0(2) . . . . ? C4 C5 C6 C1 -1.9(3) . . . . ? C4 C5 C6 C28 179.37(19) . . . . ? C4 C3 C14 O2 -82.7(2) . . . . ? C4 C3 C2 C1 -3.4(3) . . . . ? C4 C3 C2 C30 179.43(19) . . . . ? O4 C41 C42 C43 -179.4(2) . . . . ? O4 C41 C46 C45 -179.9(2) . . . . ? O4 C40 C34 C35 71.3(2) . . . . ? O4 C40 C34 C39 -111.2(2) . . . . ? C37 C38 C54 O6 90.6(2) . . . . ? C37 C38 C39 C34 7.5(3) . . . . ? C37 C38 C39 C65 -173.7(2) . . . . ? C37 C36 C47 O5 -84.9(2) . . . . ? O6 C55 C60 C59 178.5(2) . . . . ? O6 C55 C56 C57 -178.4(2) . . . . ? C41 O4 C40 C34 -179.64(18) . . . . ? C41 C42 C43 C44 -0.4(4) . . . . ? C41 C46 C45 C44 -0.8(4) . . . . ? C5 C4 C3 C14 178.53(19) . . . . ? C5 C4 C3 C2 -1.3(3) . . . . ? C5 C4 C32 C33 86.9(3) . . . . ? C3 C4 C5 C21 -177.11(18) . . . . ? C3 C4 C5 C6 4.0(3) . . . . ? C3 C4 C32 C33 -89.0(2) . . . . ? C48 O5 C47 C36 173.79(19) . . . . ? C48 C53 C52 C51 0.4(4) . . . . ? C55 O6 C54 C38 -174.69(19) . . . . ? C55 C60 C59 C58 -0.3(4) . . . . ? C55 C56 C57 C58 -0.2(4) . . . . ? C42 C41 C46 C45 1.2(3) . . . . ? C42 C43 C44 Cl4 -178.2(2) . . . . ? C42 C43 C44 C45 0.7(4) . . . . ? C8 O1 C7 C1 175.55(18) . . . . ? C8 C13 C12 C11 -0.7(3) . . . . ? C50 C51 C52 C53 -0.1(4) . . . . ? C13 C8 C9 C10 -2.1(4) . . . . ? C13 C12 C11 Cl1 177.25(18) . . . . ? C13 C12 C11 C10 -1.6(4) . . . . ? C43 C44 C45 C46 -0.2(4) . . . . ? C60 C55 C56 C57 0.4(4) . . . . ? C15 O2 C14 C3 179.48(17) . . . . ? C15 C16 C17 C18 0.0(4) . . . . ? C15 C20 C19 C18 0.1(3) . . . . ? C38 C37 C63 C64 89.9(3) . . . . ? C38 C37 C36 C35 -0.7(3) . . . . ? C38 C37 C36 C47 173.33(19) . . . . ? C53 C48 C49 C50 0.8(3) . . . . ? C51 C50 C49 C48 -0.5(3) . . . . ? C46 C41 C42 C43 -0.6(4) . . . . ? C35 C36 C47 O5 89.2(2) . . . . ? C35 C34 C39 C38 -3.7(3) . . . . ? C35 C34 C39 C65 177.4(2) . . . . ? C49 C48 C53 C52 -0.7(4) . . . . ? C49 C50 C51 Cl5 -179.83(18) . . . . ? C49 C50 C51 C52 0.1(4) . . . . ? C21 O3 C22 C23 168.4(2) . . . . ? C21 O3 C22 C27 -11.0(3) . . . . ? C21 C5 C6 C1 179.21(19) . . . . ? C21 C5 C6 C28 0.5(3) . . . . ? C63 C37 C38 C54 -4.4(3) . . . . ? C63 C37 C38 C39 173.9(2) . . . . ? C63 C37 C36 C35 -179.86(19) . . . . ? C63 C37 C36 C47 -5.8(3) . . . . ? C56 C55 C60 C59 -0.2(4) . . . . ? C22 O3 C21 C5 -168.15(18) . . . . ? C22 C23 C24 C25 -0.5(4) . . . . ? C22 C27 C26 C25 -0.3(4) . . . . ? C16 C15 C20 C19 0.5(3) . . . . ? C36 C37 C38 C54 176.39(19) . . . . ? C36 C37 C38 C39 -5.3(3) . . . . ? C36 C37 C63 C64 -90.9(3) . . . . ? C36 C35 C61 C62 78.5(3) . . . . ? C36 C35 C34 C40 175.41(18) . . . . ? C36 C35 C34 C39 -2.1(3) . . . . ? C20 C15 C16 C17 -0.6(4) . . . . ? C17 C18 C19 C20 -0.6(4) . . . . ? C9 C8 C13 C12 2.5(3) . . . . ? C9 C10 C11 Cl1 -176.89(19) . . . . ? C9 C10 C11 C12 1.9(4) . . . . ? C23 C22 C27 C26 1.0(4) . . . . ? C57 C58 C59 C60 0.5(4) . . . . ? C59 C58 C57 C56 -0.3(4) . . . . ? C47 O5 C48 C53 -175.0(2) . . . . ? C47 O5 C48 C49 5.3(3) . . . . ? C14 O2 C15 C16 -175.5(2) . . . . ? C14 O2 C15 C20 5.1(3) . . . . ? C14 C3 C2 C1 176.78(19) . . . . ? C14 C3 C2 C30 -0.4(3) . . . . ? C54 O6 C55 C60 -10.5(3) . . . . ? C54 O6 C55 C56 168.2(2) . . . . ? C54 C38 C39 C34 -174.21(19) . . . . ? C54 C38 C39 C65 4.7(3) . . . . ? C61 C35 C36 C37 -174.41(19) . . . . ? C61 C35 C36 C47 11.6(3) . . . . ? C61 C35 C34 C40 -5.9(3) . . . . ? C61 C35 C34 C39 176.63(19) . . . . ? C40 O4 C41 C42 -23.2(3) . . . . ? C40 O4 C41 C46 158.0(2) . . . . ? C40 C34 C39 C38 178.77(19) . . . . ? C40 C34 C39 C65 -0.1(3) . . . . ? C34 C35 C36 C37 4.3(3) . . . . ? C34 C35 C36 C47 -169.62(19) . . . . ? C34 C35 C61 C62 -100.2(3) . . . . ? C7 O1 C8 C13 -2.7(3) . . . . ? C7 O1 C8 C9 177.66(19) . . . . ? C7 C1 C2 C3 -172.43(19) . . . . ? C7 C1 C2 C30 4.8(3) . . . . ? C7 C1 C6 C5 175.02(19) . . . . ? C7 C1 C6 C28 -6.3(3) . . . . ? C2 C1 C7 O1 -113.1(2) . . . . ? C2 C1 C6 C5 -2.9(3) . . . . ? C2 C1 C6 C28 175.8(2) . . . . ? C2 C3 C14 O2 97.2(2) . . . . ? C27 C22 C23 C24 -0.5(4) . . . . ? C26 C25 C24 C23 1.2(4) . . . . ? C6 C5 C21 O3 -109.2(2) . . . . ? C6 C1 C7 O1 69.0(3) . . . . ? C6 C1 C2 C3 5.4(3) . . . . ? C6 C1 C2 C30 -177.36(19) . . . . ? C32 C4 C5 C21 7.0(3) . . . . ? C32 C4 C5 C6 -171.95(19) . . . . ? C32 C4 C3 C14 -5.6(3) . . . . ? C32 C4 C3 C2 174.56(19) . . . . ? C11 C10 C9 C8 -0.1(4) . . . . ? C66 C65 C39 C38 -99.9(3) . . . . ? C66 C65 C39 C34 78.9(3) . . . . ? C19 C18 C17 C16 0.5(4) . . . . ? C24 C25 C26 C27 -0.7(4) . . . . ? C29 C28 C6 C5 77.6(3) . . . . ? C29 C28 C6 C1 -101.1(2) . . . . ? C31 C30 C2 C1 -90.5(3) . . . . ? C31 C30 C2 C3 86.6(2) . . . . ? C39 C38 C54 O6 -87.8(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962407' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-gf-226K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-gf, 226 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Cl3 O3' _chemical_formula_sum 'C33 H33 Cl3 O3' _chemical_formula_weight 583.94 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/a 1' _space_group_name_Hall '-P 2yab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z' _cell_length_a 24.8803(10) _cell_length_b 13.4318(4) _cell_length_c 28.8166(11) _cell_angle_alpha 90.00 _cell_angle_beta 110.512(5) _cell_angle_gamma 90.00 _cell_volume 9019.5(6) _cell_formula_units_Z 12 _cell_measurement_reflns_used 9745 _cell_measurement_temperature 226(2) _cell_measurement_theta_max 29.1694 _cell_measurement_theta_min 3.6953 _exptl_absorpt_coefficient_mu 0.337 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.93680 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 3672 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_unetI/netI 0.0918 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_number 55419 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.23 _diffrn_reflns_theta_min 3.70 _diffrn_ambient_temperature 226(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0025959000 _diffrn_orient_matrix_UB_12 0.0506004000 _diffrn_orient_matrix_UB_13 0.0059396000 _diffrn_orient_matrix_UB_21 0.0272253000 _diffrn_orient_matrix_UB_22 -0.0024992000 _diffrn_orient_matrix_UB_23 0.0191753000 _diffrn_orient_matrix_UB_31 0.0133549000 _diffrn_orient_matrix_UB_32 0.0149036000 _diffrn_orient_matrix_UB_33 -0.0169616000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 11190 _reflns_number_total 21164 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.375 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.052 _refine_ls_extinction_coef 0.00059(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 1123 _refine_ls_number_reflns 21164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1437 _refine_ls_R_factor_gt 0.0717 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+3.8725P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1417 _refine_ls_wR_factor_ref 0.1786 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Sof(H86C)=Sof(H86D)=Sof(H93C)=Sof(H93D)=Sof(C75A)=Sof(H75C)=Sof(H75D)= Sof(C70A)=Sof(C76A)=Sof(H76D)=Sof(H76E)=Sof(H76F)=Sof(C71A)=Sof(C69A)=1-FVAR(1) Sof(C69B)=Sof(C71B)=Sof(C70B)=Sof(H86A)=Sof(H86B)=Sof(H93A)=Sof(H93B)= Sof(C75B)=Sof(H75A)=Sof(H75B)=Sof(C76B)=Sof(H76A)=Sof(H76B)=Sof(H76C)=FVAR(1) Sof(H53C)=Sof(H53D)=Sof(H60C)=Sof(H60D)=Sof(C37B)=Sof(C42B)=Sof(H42C)= Sof(H42D)=Sof(C43B)=Sof(H43D)=Sof(H43E)=Sof(H43F)=Sof(C36B)=Sof(C38B)=1-FVAR(2) Sof(C36A)=Sof(C37A)=Sof(H53A)=Sof(H53B)=Sof(C38A)=Sof(H60A)=Sof(H60B)= Sof(C43A)=Sof(H43A)=Sof(H43B)=Sof(H43C)=Sof(C42A)=Sof(H42A)=Sof(H42B)=FVAR(2) 3.a Secondary CH2 refined with riding coordinates: C46(H46A,H46B), C79(H79A,H79B), C27(H27A,H27B), C40(H40A,H40B), C11(H11A, H11B), C73(H73A,H73B), C44(H44A,H44B), C9(H9A,H9B), C13(H13A,H13B), C20(H20A, H20B), C53(H53A,H53B), C53(H53C,H53D), C77(H77A,H77B), C86(H86A,H86B), C86(H86C,H86D), C93(H93A,H93B), C93(H93C,H93D), C75B(H75A,H75B), C60(H60A, H60B), C60(H60C,H60D), C7(H7A,H7B), C42A(H42A,H42B), C75A(H75C,H75D), C42B(H42C,H42D) 3.b Aromatic/amide H refined with riding coordinates: C48(H48), C29(H29), C66(H66), C85(H85), C95(H95), C49(H49), C91(H91), C81(H81), C26(H26), C33(H33), C96(H96), C56(H56), C30(H30), C25(H25), C52(H52), C98(H98), C92(H92), C65(H65), C55(H55), C84(H84), C15(H15), C88(H88), C32(H32), C63(H63), C99(H99), C59(H59), C19(H19), C22(H22), C62(H62), C82(H82), C89(H89), C23(H23), C58(H58), C18(H18), C16(H16), C51(H51) 3.c Idealised Me refined as rotating group: C74(H74A,H74B,H74C), C12(H12A,H12B,H12C), C41(H41A,H41B,H41C), C45(H45A,H45B, H45C), C78(H78A,H78B,H78C), C8(H8A,H8B,H8C), C43A(H43A,H43B,H43C), C10(H10A, H10B,H10C), C76B(H76A,H76B,H76C), C76A(H76D,H76E,H76F), C43B(H43D,H43E,H43F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl4 Cl 0.39852(7) 0.00447(7) 0.14599(4) 0.1036(5) Uani 1 1 d . . . Cl2 Cl 0.41000(5) 0.00521(6) 0.48401(3) 0.0726(3) Uani 1 1 d . . . Cl7 Cl 0.60662(6) 0.99959(7) 0.18934(4) 0.0953(4) Uani 1 1 d . . . Cl9 Cl 0.71871(4) 0.18270(8) -0.18355(4) 0.0688(3) Uani 1 1 d . . . Cl3 Cl 0.28693(4) 0.81568(7) 0.85979(4) 0.0624(3) Uani 1 1 d . . . Cl5 Cl 0.26506(4) 0.84941(7) 0.50556(4) 0.0657(3) Uani 1 1 d . . . Cl1 Cl 0.77309(4) 1.03486(8) 0.72778(4) 0.0793(3) Uani 1 1 d . . . Cl6 Cl 0.78475(4) 1.05219(8) 0.39088(4) 0.0789(3) Uani 1 1 d . . . Cl8 Cl 0.21831(5) -0.05912(9) -0.05902(5) 0.0893(4) Uani 1 1 d . . . O3 O 0.38736(8) 0.70896(15) 0.70976(7) 0.0405(5) Uani 1 1 d . . . O9 O 0.60882(9) 0.30692(16) -0.04294(8) 0.0484(5) Uani 1 1 d . . . O5 O 0.38127(9) 0.70616(16) 0.37300(8) 0.0484(5) Uani 1 1 d . . . O1 O 0.57366(8) 0.76853(14) 0.65821(8) 0.0418(5) Uani 1 1 d . . . O8 O 0.40960(10) 0.22390(16) -0.00566(9) 0.0559(6) Uani 1 1 d A . . C28 C 0.36112(12) 0.7355(2) 0.74291(11) 0.0342(6) Uani 1 1 d . . . C80 C 0.63738(13) 0.2764(2) -0.07345(12) 0.0388(7) Uani 1 1 d . . . O4 O 0.42038(9) 0.41252(14) 0.22345(8) 0.0502(6) Uani 1 1 d B . . O2 O 0.44017(8) 0.41042(14) 0.56584(8) 0.0419(5) Uani 1 1 d . . . C47 C 0.35074(12) 0.7411(2) 0.40086(11) 0.0360(7) Uani 1 1 d . . . O6 O 0.58873(10) 0.78029(15) 0.34324(9) 0.0525(6) Uani 1 1 d B . . C46 C 0.35957(12) 0.7211(2) 0.32005(11) 0.0392(7) Uani 1 1 d . . . H46A H 0.3519 0.7918 0.3120 0.047 Uiso 1 1 calc . . R H46B H 0.3241 0.6833 0.3045 0.047 Uiso 1 1 calc . . R O7 O 0.58050(9) 0.58549(14) 0.11990(8) 0.0493(6) Uani 1 1 d A . . C79 C 0.63356(13) 0.2872(2) 0.00940(11) 0.0416(7) Uani 1 1 d . . . H79A H 0.6694 0.3243 0.0243 0.050 Uiso 1 1 calc . . R H79B H 0.6415 0.2160 0.0155 0.050 Uiso 1 1 calc . . R C35 C 0.45178(12) 0.7469(2) 0.30493(10) 0.0357(6) Uani 1 1 d . . . C48 C 0.29736(12) 0.7861(2) 0.38194(12) 0.0398(7) Uani 1 1 d . . . H48 H 0.2793 0.7943 0.3476 0.048 Uiso 1 1 calc . . R C27 C 0.35964(12) 0.7382(2) 0.65916(10) 0.0342(6) Uani 1 1 d . . . H27A H 0.3561 0.8108 0.6566 0.041 Uiso 1 1 calc . . R H27B H 0.3211 0.7090 0.6458 0.041 Uiso 1 1 calc . . R C67 C 0.58899(12) 0.3212(2) 0.03039(11) 0.0368(7) Uani 1 1 d A . . C68 C 0.54426(13) 0.2566(2) 0.02833(11) 0.0384(7) Uani 1 1 d . . . C14 C 0.61952(12) 0.8324(2) 0.67165(11) 0.0365(7) Uani 1 1 d . . . C61 C 0.41843(13) 0.3158(2) 0.20755(11) 0.0394(7) Uani 1 1 d . . . C5 C 0.39630(11) 0.70088(19) 0.63086(10) 0.0290(6) Uani 1 1 d . . . C87 C 0.36536(14) 0.1566(2) -0.01524(12) 0.0448(8) Uani 1 1 d . . . C29 C 0.30797(12) 0.7809(2) 0.72938(11) 0.0378(7) Uani 1 1 d . . . H29 H 0.2874 0.7958 0.6960 0.045 Uiso 1 1 calc . . R C34 C 0.40662(12) 0.6836(2) 0.30313(10) 0.0348(6) Uani 1 1 d B . . C6 C 0.44387(11) 0.75704(18) 0.63120(10) 0.0293(6) Uani 1 1 d . . . C66 C 0.46200(13) 0.2481(2) 0.22638(12) 0.0434(7) Uani 1 1 d . . . H66 H 0.4957 0.2664 0.2523 0.052 Uiso 1 1 calc . . R C85 C 0.69035(12) 0.2293(2) -0.05688(12) 0.0414(7) Uani 1 1 d . . . H85 H 0.7093 0.2169 -0.0229 0.050 Uiso 1 1 calc . . R C21 C 0.43073(12) 0.31920(19) 0.54305(10) 0.0327(6) Uani 1 1 d . . . C54 C 0.63452(13) 0.8431(2) 0.35141(12) 0.0396(7) Uani 1 1 d . . . C95 C 0.54125(14) 0.7527(2) 0.11342(12) 0.0478(8) Uani 1 1 d . . . H95 H 0.5077 0.7343 0.0873 0.057 Uiso 1 1 calc . . R C40 C 0.45157(14) 0.8556(2) 0.31998(12) 0.0428(7) Uani 1 1 d B . . H40A H 0.4912 0.8775 0.3369 0.051 Uiso 1 1 calc . . R H40B H 0.4312 0.8614 0.3435 0.051 Uiso 1 1 calc . . R C49 C 0.27064(13) 0.8192(2) 0.41439(13) 0.0434(7) Uani 1 1 d . . . H49 H 0.2342 0.8491 0.4019 0.052 Uiso 1 1 calc . . R C91 C 0.30792(17) 0.0361(3) 0.00686(14) 0.0641(10) Uani 1 1 d . . . H91 H 0.2992 -0.0009 0.0310 0.077 Uiso 1 1 calc . . R C94 C 0.58377(13) 0.6833(2) 0.13434(11) 0.0392(7) Uani 1 1 d . . . C81 C 0.61023(14) 0.2945(2) -0.12336(12) 0.0487(8) Uani 1 1 d . . . H81 H 0.5743 0.3264 -0.1343 0.058 Uiso 1 1 calc . . R C11 C 0.45539(12) 0.8587(2) 0.65514(11) 0.0387(7) Uani 1 1 d . . . H11A H 0.4968 0.8714 0.6677 0.046 Uiso 1 1 calc . . R H11B H 0.4419 0.8604 0.6832 0.046 Uiso 1 1 calc . . R C26 C 0.47379(13) 0.2498(2) 0.56305(11) 0.0419(7) Uani 1 1 d . . . H26 H 0.5072 0.2678 0.5895 0.050 Uiso 1 1 calc . . R C33 C 0.39081(13) 0.7131(2) 0.79211(11) 0.0451(8) Uani 1 1 d . . . H33 H 0.4268 0.6816 0.8010 0.054 Uiso 1 1 calc . . R C96 C 0.54826(16) 0.8501(2) 0.13110(12) 0.0537(9) Uani 1 1 d . . . H96 H 0.5192 0.8975 0.1173 0.064 Uiso 1 1 calc . . R C56 C 0.69235(14) 0.9601(2) 0.32689(13) 0.0503(8) Uani 1 1 d . . . H56 H 0.7002 0.9964 0.3021 0.060 Uiso 1 1 calc . . R C30 C 0.28525(12) 0.8045(2) 0.76607(12) 0.0409(7) Uani 1 1 d . . . H30 H 0.2491 0.8351 0.7573 0.049 Uiso 1 1 calc . . R C72 C 0.59030(13) 0.4194(2) 0.04727(11) 0.0384(7) Uani 1 1 d . . . C90 C 0.27537(15) 0.0250(3) -0.04263(14) 0.0553(9) Uani 1 1 d . . . C25 C 0.46781(14) 0.1540(2) 0.54424(12) 0.0475(8) Uani 1 1 d . . . H25 H 0.4970 0.1068 0.5578 0.057 Uiso 1 1 calc . . R C52 C 0.37710(13) 0.7299(2) 0.45186(12) 0.0439(8) Uani 1 1 d . . . H52 H 0.4133 0.6992 0.4647 0.053 Uiso 1 1 calc . . R C73 C 0.54211(14) 0.1506(2) 0.00928(12) 0.0444(7) Uani 1 1 d A . . H73A H 0.5019 0.1308 -0.0066 0.053 Uiso 1 1 calc . . R H73B H 0.5602 0.1488 -0.0160 0.053 Uiso 1 1 calc . . R C74 C 0.57204(17) 0.0762(2) 0.04979(15) 0.0669(11) Uani 1 1 d . . . H74A H 0.5673 0.0096 0.0359 0.100 Uiso 1 1 calc A . GR H74B H 0.5553 0.0793 0.0755 0.100 Uiso 1 1 calc . . GR H74C H 0.6126 0.0921 0.0638 0.100 Uiso 1 1 calc . . GR C44 C 0.35553(13) 0.5177(2) 0.28305(12) 0.0457(8) Uani 1 1 d B . . H44A H 0.3407 0.5312 0.3098 0.055 Uiso 1 1 calc . . R H44B H 0.3671 0.4477 0.2853 0.055 Uiso 1 1 calc . . R C64 C 0.40643(17) 0.1257(2) 0.16908(12) 0.0562(9) Uani 1 1 d . . . C98 C 0.63989(15) 0.8081(3) 0.18963(13) 0.0537(9) Uani 1 1 d . . . H98 H 0.6735 0.8268 0.2156 0.064 Uiso 1 1 calc . . R C92 C 0.35330(16) 0.1019(3) 0.02054(13) 0.0578(9) Uani 1 1 d . . . H92 H 0.3760 0.1096 0.0541 0.069 Uiso 1 1 calc . . R C65 C 0.45597(16) 0.1522(2) 0.20690(13) 0.0545(9) Uani 1 1 d . . . H65 H 0.4857 0.1056 0.2196 0.065 Uiso 1 1 calc . . R C83 C 0.68722(14) 0.2192(2) -0.14066(13) 0.0438(8) Uani 1 1 d . . . C57 C 0.72691(13) 0.9700(2) 0.37582(13) 0.0469(8) Uani 1 1 d . . . C55 C 0.64584(14) 0.8959(2) 0.31460(12) 0.0480(8) Uani 1 1 d . . . H55 H 0.6220 0.8883 0.2813 0.058 Uiso 1 1 calc . . R C50 C 0.29768(13) 0.8078(2) 0.46441(12) 0.0408(7) Uani 1 1 d . . . C1 C 0.47936(11) 0.72049(19) 0.60593(10) 0.0304(6) Uani 1 1 d . . . C84 C 0.71517(13) 0.2006(2) -0.09148(13) 0.0437(8) Uani 1 1 d . . . H84 H 0.7510 0.1685 -0.0809 0.052 Uiso 1 1 calc . . R C15 C 0.63308(14) 0.8950(2) 0.63954(12) 0.0479(8) Uani 1 1 d . . . H15 H 0.6103 0.8955 0.6057 0.058 Uiso 1 1 calc . . R C88 C 0.33225(15) 0.1438(2) -0.06487(13) 0.0518(9) Uani 1 1 d . . . H88 H 0.3407 0.1803 -0.0893 0.062 Uiso 1 1 calc . . R C32 C 0.36832(14) 0.7364(2) 0.82824(12) 0.0470(8) Uani 1 1 d . . . H32 H 0.3886 0.7207 0.8616 0.056 Uiso 1 1 calc . . R C17 C 0.71332(12) 0.9569(2) 0.70626(13) 0.0465(8) Uani 1 1 d . . . C63 C 0.36272(16) 0.1933(3) 0.15029(12) 0.0582(9) Uani 1 1 d . . . H63 H 0.3288 0.1747 0.1246 0.070 Uiso 1 1 calc . . R C31 C 0.31566(13) 0.7830(2) 0.81471(12) 0.0401(7) Uani 1 1 d . . . C99 C 0.63292(14) 0.7109(2) 0.17252(12) 0.0481(8) Uani 1 1 d . . . H99 H 0.6618 0.6636 0.1870 0.058 Uiso 1 1 calc . . R C24 C 0.41871(14) 0.1281(2) 0.50542(11) 0.0416(7) Uani 1 1 d . . . C59 C 0.66979(14) 0.8545(2) 0.40037(12) 0.0480(8) Uani 1 1 d . . . H59 H 0.6623 0.8188 0.4255 0.058 Uiso 1 1 calc . . R C69B C 0.4971(3) 0.2918(4) 0.0420(2) 0.0371(11) Uani 0.791(9) 1 d A 3 . C19 C 0.65327(13) 0.8331(2) 0.72167(12) 0.0450(8) Uani 1 1 d . . . H19 H 0.6441 0.7907 0.7438 0.054 Uiso 1 1 calc . . R C36A C 0.5015(2) 0.7073(4) 0.2975(2) 0.0340(11) Uani 0.767(13) 1 d B 1 . C22 C 0.38274(12) 0.2933(2) 0.50324(11) 0.0361(7) Uani 1 1 d . . . H22 H 0.3541 0.3409 0.4886 0.043 Uiso 1 1 calc . . R C39 C 0.40723(12) 0.5831(2) 0.28966(11) 0.0363(7) Uani 1 1 d . . . C12 C 0.42502(15) 0.9395(2) 0.61800(14) 0.0541(9) Uani 1 1 d . . . H12A H 0.4338 1.0042 0.6338 0.081 Uiso 1 1 calc . . GR H12B H 0.3839 0.9284 0.6065 0.081 Uiso 1 1 calc . . GR H12C H 0.4381 0.9373 0.5900 0.081 Uiso 1 1 calc . . GR C9 C 0.33175(11) 0.5501(2) 0.60590(11) 0.0377(7) Uani 1 1 d . . . H9A H 0.3274 0.5581 0.6382 0.045 Uiso 1 1 calc . . R H9B H 0.3387 0.4795 0.6017 0.045 Uiso 1 1 calc . . R C97 C 0.59778(16) 0.8768(2) 0.16876(12) 0.0530(9) Uani 1 1 d . . . C71B C 0.5407(2) 0.4553(4) 0.0579(2) 0.0361(11) Uani 0.791(9) 1 d A 3 . C3 C 0.41645(11) 0.57823(19) 0.57756(10) 0.0307(6) Uani 1 1 d . . . C62 C 0.36896(14) 0.2886(2) 0.16928(12) 0.0500(8) Uani 1 1 d . . . H62 H 0.3394 0.3354 0.1561 0.060 Uiso 1 1 calc . . R C41 C 0.42316(16) 0.9240(2) 0.27593(14) 0.0620(10) Uani 1 1 d . . . H41A H 0.4420 0.9164 0.2518 0.093 Uiso 1 1 calc B . GR H41B H 0.4265 0.9926 0.2872 0.093 Uiso 1 1 calc . . GR H41C H 0.3829 0.9066 0.2608 0.093 Uiso 1 1 calc . . GR C13 C 0.53173(12) 0.7801(2) 0.60850(11) 0.0370(7) Uani 1 1 d . . . H13A H 0.5475 0.7557 0.5839 0.044 Uiso 1 1 calc . . R H13B H 0.5216 0.8504 0.6017 0.044 Uiso 1 1 calc . . R C82 C 0.63480(14) 0.2667(2) -0.15743(12) 0.0478(8) Uani 1 1 d . . . H82 H 0.6162 0.2797 -0.1914 0.057 Uiso 1 1 calc . . R C89 C 0.28747(15) 0.0782(3) -0.07823(14) 0.0568(9) Uani 1 1 d . . . H89 H 0.2650 0.0697 -0.1118 0.068 Uiso 1 1 calc . . R C23 C 0.37679(13) 0.1966(2) 0.48488(11) 0.0416(7) Uani 1 1 d . . . H23 H 0.3437 0.1785 0.4582 0.050 Uiso 1 1 calc . . R C58 C 0.71554(14) 0.9180(3) 0.41194(13) 0.0527(9) Uani 1 1 d . . . H58 H 0.7394 0.9259 0.4452 0.063 Uiso 1 1 calc . . R C18 C 0.69990(13) 0.8953(2) 0.73900(13) 0.0497(8) Uani 1 1 d . . . H18 H 0.7225 0.8960 0.7729 0.060 Uiso 1 1 calc . . R C45 C 0.30802(15) 0.5365(3) 0.23301(14) 0.0615(10) Uani 1 1 d . . . H45A H 0.3217 0.5188 0.2065 0.092 Uiso 1 1 calc B . GR H45B H 0.2974 0.6063 0.2303 0.092 Uiso 1 1 calc . . GR H45C H 0.2748 0.4962 0.2306 0.092 Uiso 1 1 calc . . GR C20 C 0.39879(12) 0.48683(19) 0.54550(11) 0.0364(7) Uani 1 1 d . . . H20A H 0.3609 0.4644 0.5444 0.044 Uiso 1 1 calc . . R H20B H 0.3966 0.5022 0.5116 0.044 Uiso 1 1 calc . . R C16 C 0.68014(15) 0.9572(2) 0.65699(14) 0.0549(9) Uani 1 1 d . . . H16 H 0.6894 0.9999 0.6350 0.066 Uiso 1 1 calc . . R C37A C 0.5054(2) 0.6054(4) 0.2891(2) 0.0343(11) Uani 0.767(13) 1 d B 1 . C51 C 0.35088(13) 0.7629(2) 0.48356(12) 0.0437(7) Uani 1 1 d . . . H51 H 0.3689 0.7551 0.5180 0.052 Uiso 1 1 calc . . R C53 C 0.54689(14) 0.7782(2) 0.29444(13) 0.0506(9) Uani 1 1 d . . . H53A H 0.5639 0.7545 0.2705 0.061 Uiso 0.767(13) 1 calc B 1 R H53B H 0.5307 0.8446 0.2844 0.061 Uiso 0.767(13) 1 calc B 1 R H53C H 0.5662 0.7525 0.2726 0.061 Uiso 0.233(13) 1 calc B 2 R H53D H 0.5368 0.8476 0.2847 0.061 Uiso 0.233(13) 1 calc B 2 R C4 C 0.38332(11) 0.61007(19) 0.60538(10) 0.0300(6) Uani 1 1 d . . . C70B C 0.4954(2) 0.3925(3) 0.05492(17) 0.0357(11) Uani 0.791(9) 1 d A 3 . C77 C 0.64151(14) 0.4855(2) 0.05360(12) 0.0469(8) Uani 1 1 d A . . H77A H 0.6299 0.5554 0.0530 0.056 Uiso 1 1 calc . . R H77B H 0.6550 0.4748 0.0258 0.056 Uiso 1 1 calc . . R C86 C 0.45203(15) 0.2211(2) 0.04327(13) 0.0510(9) Uani 1 1 d . . . H86A H 0.4678 0.1539 0.0514 0.061 Uiso 0.791(9) 1 calc A 3 R H86B H 0.4354 0.2417 0.0680 0.061 Uiso 0.791(9) 1 calc A 3 R H86C H 0.4617 0.1510 0.0515 0.061 Uiso 0.209(9) 1 calc A 4 R H86D H 0.4337 0.2456 0.0662 0.061 Uiso 0.209(9) 1 calc A 4 R C38A C 0.4587(2) 0.5432(4) 0.2845(2) 0.0327(11) Uani 0.767(13) 1 d B 1 . C78 C 0.69077(15) 0.4644(3) 0.10247(14) 0.0625(10) Uani 1 1 d . . . H78A H 0.7029 0.3956 0.1029 0.094 Uiso 1 1 calc A . GR H78B H 0.6778 0.4760 0.1300 0.094 Uiso 1 1 calc . . GR H78C H 0.7228 0.5081 0.1053 0.094 Uiso 1 1 calc . . GR C93 C 0.53976(15) 0.5635(2) 0.07171(13) 0.0504(8) Uani 1 1 d . . . H93A H 0.5481 0.6049 0.0471 0.061 Uiso 0.791(9) 1 calc A 3 R H93B H 0.5012 0.5807 0.0710 0.061 Uiso 0.791(9) 1 calc A 3 R H93C H 0.5462 0.6029 0.0455 0.061 Uiso 0.209(9) 1 calc A 4 R H93D H 0.5000 0.5708 0.0701 0.061 Uiso 0.209(9) 1 calc A 4 R C8 C 0.55805(13) 0.5432(2) 0.58681(13) 0.0501(8) Uani 1 1 d . . . H8A H 0.5805 0.5913 0.6109 0.075 Uiso 1 1 calc . . GR H8B H 0.5806 0.5181 0.5678 0.075 Uiso 1 1 calc . . GR H8C H 0.5475 0.4884 0.6038 0.075 Uiso 1 1 calc . . GR C2 C 0.46566(11) 0.63135(19) 0.57920(10) 0.0299(6) Uani 1 1 d . . . C75B C 0.4431(2) 0.4311(3) 0.06521(17) 0.0461(13) Uani 0.791(9) 1 d A 3 . H75A H 0.4327 0.4969 0.0500 0.055 Uiso 0.791(9) 1 calc A 3 R H75B H 0.4107 0.3862 0.0501 0.055 Uiso 0.791(9) 1 calc A 3 R C60 C 0.46027(14) 0.4349(2) 0.27235(13) 0.0462(8) Uani 1 1 d . . . H60A H 0.4992 0.4169 0.2743 0.055 Uiso 0.767(13) 1 calc B 1 R H60B H 0.4507 0.3949 0.2968 0.055 Uiso 0.767(13) 1 calc B 1 R H60C H 0.5002 0.4222 0.2757 0.055 Uiso 0.233(13) 1 calc B 2 R H60D H 0.4510 0.4002 0.2985 0.055 Uiso 0.233(13) 1 calc B 2 R C7 C 0.50383(12) 0.5931(2) 0.55192(11) 0.0369(7) Uani 1 1 d . . . H7A H 0.5147 0.6488 0.5351 0.044 Uiso 1 1 calc . . R H7B H 0.4823 0.5451 0.5266 0.044 Uiso 1 1 calc . . R C43A C 0.5560(3) 0.5491(5) 0.2317(2) 0.066(2) Uani 0.767(13) 1 d B 1 . H43A H 0.5458 0.6117 0.2140 0.099 Uiso 0.767(13) 1 calc B 1 GR H43B H 0.5265 0.5000 0.2163 0.099 Uiso 0.767(13) 1 calc B 1 GR H43C H 0.5925 0.5261 0.2306 0.099 Uiso 0.767(13) 1 calc B 1 GR C10 C 0.27620(13) 0.5817(2) 0.56535(13) 0.0524(9) Uani 1 1 d . . . H10A H 0.2686 0.6512 0.5697 0.079 Uiso 1 1 calc . . GR H10B H 0.2447 0.5413 0.5673 0.079 Uiso 1 1 calc . . GR H10C H 0.2799 0.5726 0.5332 0.079 Uiso 1 1 calc . . GR C76B C 0.4545(2) 0.4388(4) 0.12009(19) 0.0657(17) Uani 0.791(9) 1 d A 3 . H76A H 0.4206 0.4643 0.1253 0.099 Uiso 0.791(9) 1 calc A 3 GR H76B H 0.4865 0.4837 0.1351 0.099 Uiso 0.791(9) 1 calc A 3 GR H76C H 0.4638 0.3735 0.1351 0.099 Uiso 0.791(9) 1 calc A 3 GR C42A C 0.5607(3) 0.5639(4) 0.28477(19) 0.0429(15) Uani 0.767(13) 1 d B 1 . H42A H 0.5924 0.6098 0.3009 0.051 Uiso 0.767(13) 1 calc B 1 R H42B H 0.5698 0.5000 0.3022 0.051 Uiso 0.767(13) 1 calc B 1 R C75A C 0.4809(6) 0.4060(11) 0.1085(5) 0.033(4) Uiso 0.209(9) 1 d A 4 . H75C H 0.5005 0.4601 0.1308 0.040 Uiso 0.209(9) 1 calc A 4 R H75D H 0.4781 0.3495 0.1290 0.040 Uiso 0.209(9) 1 calc A 4 R C37B C 0.4871(8) 0.6195(11) 0.2651(9) 0.032(4) Uani 0.233(13) 1 d B 2 . C42B C 0.5292(7) 0.5854(12) 0.2420(7) 0.047(5) Uani 0.233(13) 1 d B 2 . H42C H 0.5355 0.6395 0.2217 0.056 Uiso 0.233(13) 1 calc B 2 R H42D H 0.5125 0.5293 0.2199 0.056 Uiso 0.233(13) 1 calc B 2 R C70A C 0.5166(8) 0.3757(13) 0.0781(8) 0.040(4) Uiso 0.209(9) 1 d A 4 . C76A C 0.4190(9) 0.4412(14) 0.0771(8) 0.058(6) Uiso 0.209(9) 1 d A 4 . H76D H 0.3994 0.3888 0.0542 0.087 Uiso 0.209(9) 1 calc A 4 GR H76E H 0.4212 0.5004 0.0586 0.087 Uiso 0.209(9) 1 calc A 4 GR H76F H 0.3979 0.4560 0.0989 0.087 Uiso 0.209(9) 1 calc A 4 GR C43B C 0.5888(10) 0.5524(17) 0.2807(9) 0.075(7) Uani 0.233(13) 1 d B 2 . H43D H 0.6129 0.5269 0.2633 0.112 Uiso 0.233(13) 1 calc B 2 GR H43E H 0.5828 0.5007 0.3019 0.112 Uiso 0.233(13) 1 calc B 2 GR H43F H 0.6073 0.6092 0.3007 0.112 Uiso 0.233(13) 1 calc B 2 GR C36B C 0.4872(7) 0.7178(11) 0.2811(6) 0.021(4) Uiso 0.233(13) 1 d B 2 . C38B C 0.4446(8) 0.5545(13) 0.2694(7) 0.028(4) Uiso 0.233(13) 1 d B 2 . C71A C 0.5589(9) 0.4455(17) 0.0711(8) 0.036(6) Uiso 0.209(9) 1 d A 4 . C69A C 0.5140(8) 0.2831(15) 0.0558(7) 0.028(5) Uiso 0.209(9) 1 d A 4 . 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 Cl4 0.1992(14) 0.0396(5) 0.0476(6) -0.0097(5) 0.0126(7) -0.0197(7) Cl2 0.1305(9) 0.0299(4) 0.0485(5) -0.0063(4) 0.0201(6) -0.0023(5) Cl7 0.1745(12) 0.0374(5) 0.0520(6) -0.0111(5) 0.0124(7) -0.0259(6) Cl9 0.0699(6) 0.0833(7) 0.0693(6) -0.0010(5) 0.0447(5) 0.0105(5) Cl3 0.0685(6) 0.0759(6) 0.0577(6) -0.0095(5) 0.0408(5) 0.0014(5) Cl5 0.0751(6) 0.0655(6) 0.0751(7) 0.0066(5) 0.0496(6) 0.0188(5) Cl1 0.0585(6) 0.0757(7) 0.0867(8) -0.0076(6) 0.0043(5) -0.0313(5) Cl6 0.0521(5) 0.0982(8) 0.0749(7) -0.0203(6) 0.0080(5) -0.0291(5) Cl8 0.0776(7) 0.0963(8) 0.0820(8) -0.0198(7) 0.0130(6) -0.0352(6) O3 0.0395(11) 0.0545(12) 0.0295(11) -0.0001(10) 0.0148(9) 0.0132(10) O9 0.0510(13) 0.0612(14) 0.0350(12) 0.0040(11) 0.0173(10) 0.0159(11) O5 0.0447(12) 0.0645(14) 0.0379(12) 0.0056(11) 0.0167(10) 0.0197(11) O1 0.0355(11) 0.0432(12) 0.0412(12) 0.0095(10) 0.0065(9) -0.0091(9) O8 0.0669(15) 0.0478(13) 0.0547(15) 0.0015(12) 0.0235(13) -0.0141(12) C28 0.0346(15) 0.0354(15) 0.0349(16) -0.0029(13) 0.0151(13) 0.0004(13) C80 0.0396(16) 0.0374(16) 0.0412(17) -0.0039(14) 0.0165(14) 0.0011(13) O4 0.0601(14) 0.0324(11) 0.0505(14) -0.0001(10) 0.0098(11) 0.0061(10) O2 0.0407(11) 0.0304(10) 0.0430(12) -0.0071(9) 0.0003(10) 0.0021(9) C47 0.0365(15) 0.0342(15) 0.0394(16) 0.0022(13) 0.0157(14) 0.0062(13) O6 0.0608(14) 0.0446(12) 0.0573(15) -0.0020(11) 0.0270(13) -0.0162(11) C46 0.0373(16) 0.0430(16) 0.0342(16) 0.0026(14) 0.0086(13) 0.0035(13) O7 0.0644(14) 0.0326(11) 0.0492(14) -0.0049(10) 0.0177(12) -0.0004(10) C79 0.0475(18) 0.0417(16) 0.0347(16) -0.0001(14) 0.0132(14) 0.0028(14) C35 0.0432(16) 0.0312(14) 0.0329(15) -0.0031(13) 0.0136(13) -0.0020(13) C48 0.0373(16) 0.0359(15) 0.0435(18) 0.0028(14) 0.0106(14) 0.0006(13) C27 0.0344(15) 0.0382(15) 0.0290(14) -0.0032(13) 0.0097(12) 0.0044(13) C67 0.0463(17) 0.0320(15) 0.0328(15) -0.0014(13) 0.0146(14) 0.0002(13) C68 0.0487(18) 0.0294(14) 0.0351(16) -0.0013(13) 0.0123(14) -0.0015(14) C14 0.0333(15) 0.0366(15) 0.0404(17) 0.0018(14) 0.0136(13) -0.0020(13) C61 0.0459(17) 0.0314(15) 0.0403(17) 0.0013(14) 0.0143(14) -0.0015(14) C5 0.0294(13) 0.0310(14) 0.0242(13) -0.0013(11) 0.0064(11) 0.0022(11) C87 0.057(2) 0.0353(16) 0.0474(19) -0.0009(15) 0.0247(17) -0.0015(15) C29 0.0356(15) 0.0428(16) 0.0347(16) -0.0013(14) 0.0118(13) 0.0022(13) C34 0.0388(15) 0.0342(15) 0.0306(15) 0.0023(13) 0.0112(13) -0.0004(13) C6 0.0323(14) 0.0250(13) 0.0269(14) -0.0002(11) 0.0057(12) 0.0016(11) C66 0.0491(18) 0.0322(15) 0.0431(18) 0.0004(14) 0.0087(15) -0.0026(14) C85 0.0399(17) 0.0389(16) 0.0429(18) 0.0010(14) 0.0114(14) 0.0018(14) C21 0.0369(15) 0.0267(14) 0.0350(15) -0.0018(12) 0.0131(13) -0.0027(12) C54 0.0450(17) 0.0297(15) 0.0503(19) -0.0022(14) 0.0242(16) -0.0024(13) C95 0.055(2) 0.0370(16) 0.0438(19) -0.0037(15) 0.0074(16) -0.0024(15) C40 0.0522(18) 0.0299(15) 0.0433(18) -0.0077(14) 0.0129(15) -0.0015(14) C49 0.0325(15) 0.0402(17) 0.057(2) 0.0028(16) 0.0157(15) 0.0045(13) C91 0.084(3) 0.064(2) 0.045(2) -0.0069(19) 0.024(2) -0.030(2) C94 0.0492(18) 0.0324(15) 0.0398(17) -0.0006(14) 0.0206(15) -0.0051(14) C81 0.0453(18) 0.060(2) 0.0420(18) 0.0026(17) 0.0162(16) 0.0120(16) C11 0.0402(16) 0.0324(15) 0.0434(18) -0.0105(14) 0.0145(14) -0.0022(13) C26 0.0440(17) 0.0381(16) 0.0332(16) 0.0019(14) 0.0004(13) 0.0035(14) C33 0.0424(17) 0.0561(19) 0.0357(17) 0.0034(15) 0.0124(14) 0.0092(15) C96 0.076(2) 0.0352(16) 0.0396(18) 0.0035(15) 0.0072(17) 0.0072(17) C56 0.056(2) 0.0532(19) 0.0439(19) -0.0081(16) 0.0209(16) -0.0198(17) C30 0.0343(15) 0.0379(16) 0.051(2) -0.0057(15) 0.0157(15) 0.0006(13) C72 0.0496(18) 0.0326(15) 0.0345(16) 0.0029(13) 0.0166(14) -0.0033(14) C90 0.058(2) 0.050(2) 0.057(2) -0.0055(18) 0.0198(19) -0.0059(17) C25 0.063(2) 0.0328(16) 0.0407(18) 0.0033(14) 0.0106(16) 0.0133(15) C52 0.0366(16) 0.0528(19) 0.0410(18) 0.0074(15) 0.0120(14) 0.0152(14) C73 0.0544(19) 0.0304(15) 0.0433(18) -0.0091(14) 0.0108(15) 0.0031(14) C74 0.078(3) 0.0300(17) 0.077(3) 0.0073(18) 0.008(2) 0.0048(17) C44 0.0463(18) 0.0373(16) 0.053(2) 0.0060(15) 0.0165(16) -0.0061(14) C64 0.094(3) 0.0370(17) 0.0311(17) -0.0020(15) 0.0142(18) -0.0154(19) C98 0.059(2) 0.056(2) 0.0399(18) -0.0003(17) 0.0094(16) -0.0203(18) C92 0.077(2) 0.059(2) 0.0369(18) -0.0047(17) 0.0194(18) -0.0251(19) C65 0.077(2) 0.0353(17) 0.046(2) 0.0018(16) 0.0149(19) 0.0052(17) C83 0.0456(18) 0.0409(17) 0.052(2) -0.0044(15) 0.0258(16) -0.0038(14) C57 0.0391(17) 0.0487(18) 0.050(2) -0.0147(17) 0.0113(15) -0.0030(15) C55 0.055(2) 0.0510(19) 0.0385(17) -0.0097(16) 0.0170(16) -0.0202(16) C50 0.0439(17) 0.0328(15) 0.052(2) 0.0008(15) 0.0245(16) -0.0039(14) C1 0.0289(14) 0.0308(14) 0.0291(14) 0.0052(12) 0.0072(12) 0.0016(12) C84 0.0379(17) 0.0377(16) 0.057(2) -0.0018(16) 0.0186(16) 0.0019(14) C15 0.054(2) 0.0529(19) 0.0369(17) -0.0058(16) 0.0165(15) -0.0192(16) C88 0.067(2) 0.0482(19) 0.0436(19) 0.0097(17) 0.0241(18) 0.0124(18) C32 0.054(2) 0.0553(19) 0.0346(17) -0.0010(15) 0.0188(15) 0.0015(16) C17 0.0328(16) 0.0440(18) 0.056(2) -0.0098(16) 0.0074(15) -0.0095(14) C63 0.064(2) 0.062(2) 0.0364(18) 0.0017(18) 0.0031(17) -0.0213(19) C31 0.0466(18) 0.0387(16) 0.0428(18) -0.0069(14) 0.0254(15) -0.0066(14) C99 0.0456(18) 0.0511(19) 0.0449(19) 0.0011(16) 0.0123(16) -0.0001(15) C24 0.065(2) 0.0290(15) 0.0313(16) -0.0043(13) 0.0172(15) -0.0018(15) C59 0.057(2) 0.0473(18) 0.0427(19) 0.0078(16) 0.0208(17) 0.0106(17) C69B 0.042(3) 0.031(2) 0.034(3) 0.004(2) 0.008(2) -0.002(2) C19 0.0390(17) 0.0473(18) 0.0448(18) 0.0140(16) 0.0099(15) 0.0010(14) C36A 0.035(2) 0.034(2) 0.026(2) 0.005(2) 0.002(2) -0.0046(19) C22 0.0319(15) 0.0373(15) 0.0360(16) -0.0054(13) 0.0082(13) 0.0016(12) C39 0.0390(16) 0.0360(15) 0.0337(16) 0.0019(13) 0.0126(13) -0.0072(13) C12 0.061(2) 0.0300(16) 0.067(2) -0.0009(16) 0.0176(19) 0.0061(15) C9 0.0340(15) 0.0381(16) 0.0407(17) 0.0022(14) 0.0128(14) -0.0032(13) C97 0.085(3) 0.0350(17) 0.0333(17) -0.0026(15) 0.0140(18) -0.0160(18) C71B 0.041(3) 0.028(2) 0.033(3) -0.005(2) 0.006(2) 0.000(2) C3 0.0332(14) 0.0278(13) 0.0290(14) 0.0004(12) 0.0082(12) 0.0021(12) C62 0.0458(18) 0.0504(19) 0.0452(19) 0.0045(16) 0.0053(16) -0.0005(16) C41 0.074(2) 0.0362(17) 0.064(2) 0.0037(18) 0.010(2) 0.0024(17) C13 0.0402(16) 0.0362(15) 0.0332(16) 0.0028(13) 0.0110(13) -0.0045(13) C82 0.0521(19) 0.056(2) 0.0396(18) 0.0050(16) 0.0211(16) 0.0056(16) C89 0.058(2) 0.060(2) 0.046(2) -0.0043(18) 0.0108(18) 0.0067(19) C23 0.0471(18) 0.0400(16) 0.0364(17) -0.0095(14) 0.0128(14) -0.0113(14) C58 0.051(2) 0.062(2) 0.0397(18) -0.0025(17) 0.0084(16) 0.0100(18) C18 0.0395(17) 0.0534(19) 0.0452(19) 0.0029(17) 0.0012(15) 0.0000(15) C45 0.053(2) 0.052(2) 0.066(3) -0.0024(19) 0.0040(19) -0.0104(17) C20 0.0326(15) 0.0340(15) 0.0393(16) -0.0050(13) 0.0086(13) 0.0040(12) C16 0.059(2) 0.0500(19) 0.056(2) -0.0050(18) 0.0213(19) -0.0235(17) C37A 0.035(3) 0.034(2) 0.029(3) 0.003(2) 0.005(2) -0.0003(19) C51 0.0457(18) 0.0472(18) 0.0378(17) 0.0042(15) 0.0141(15) 0.0060(15) C53 0.058(2) 0.0406(17) 0.062(2) -0.0124(17) 0.0313(19) -0.0157(16) C4 0.0298(14) 0.0307(14) 0.0279(14) 0.0022(12) 0.0080(12) -0.0010(12) C70B 0.045(2) 0.030(2) 0.031(2) 0.0017(18) 0.013(2) -0.0005(18) C77 0.0556(19) 0.0379(16) 0.0467(19) 0.0016(15) 0.0174(16) -0.0093(15) C86 0.064(2) 0.0357(17) 0.059(2) -0.0057(16) 0.0283(19) -0.0114(16) C38A 0.036(3) 0.029(2) 0.026(2) 0.002(2) 0.002(2) 0.0000(19) C78 0.066(2) 0.054(2) 0.055(2) -0.0024(19) 0.0061(19) -0.0164(19) C93 0.059(2) 0.0387(17) 0.052(2) -0.0144(16) 0.0172(17) -0.0093(16) C8 0.0378(17) 0.057(2) 0.056(2) -0.0003(17) 0.0169(16) 0.0099(15) C2 0.0304(14) 0.0323(14) 0.0270(14) 0.0008(12) 0.0100(12) 0.0056(12) C75B 0.049(3) 0.043(2) 0.048(3) -0.001(2) 0.019(2) -0.001(2) C60 0.0468(18) 0.0384(16) 0.052(2) -0.0061(15) 0.0153(16) -0.0051(14) C7 0.0370(16) 0.0416(16) 0.0331(15) -0.0027(14) 0.0135(13) 0.0005(13) C43A 0.067(4) 0.072(4) 0.065(4) -0.014(3) 0.031(3) -0.004(3) C10 0.0362(17) 0.058(2) 0.057(2) -0.0008(18) 0.0092(16) -0.0070(15) C76B 0.068(4) 0.080(3) 0.055(3) -0.001(3) 0.030(3) 0.002(3) C42A 0.036(3) 0.039(2) 0.051(3) 0.000(2) 0.013(3) -0.004(2) C37B 0.029(8) 0.034(7) 0.040(10) 0.002(7) 0.020(8) 0.011(6) C42B 0.042(9) 0.040(8) 0.068(12) 0.002(8) 0.031(9) 0.005(7) C43B 0.034(11) 0.084(14) 0.103(18) -0.010(12) 0.021(11) -0.005(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl4 C64 1.743(3) . ? Cl2 C24 1.748(3) . ? Cl7 C97 1.740(3) . ? Cl9 C83 1.749(3) . ? Cl3 C31 1.744(3) . ? Cl5 C50 1.747(3) . ? Cl1 C17 1.746(3) . ? Cl6 C57 1.744(3) . ? Cl8 C90 1.745(3) . ? O3 C28 1.379(3) . ? O3 C27 1.432(3) . ? O9 C80 1.373(3) . ? O9 C79 1.440(3) . ? O5 C47 1.367(3) . ? O5 C46 1.443(3) . ? O1 C14 1.370(3) . ? O1 C13 1.455(3) . ? O8 C87 1.376(4) . ? O8 C86 1.436(4) . ? C28 C29 1.383(4) . ? C28 C33 1.383(4) . ? C80 C85 1.387(4) . ? C80 C81 1.380(4) . ? O4 C61 1.373(3) . ? O4 C60 1.442(4) . ? O2 C21 1.371(3) . ? O2 C20 1.426(3) . ? C47 C48 1.385(4) . ? C47 C52 1.392(4) . ? O6 C54 1.370(3) . ? O6 C53 1.427(4) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 C34 1.504(4) . ? O7 C94 1.372(3) . ? O7 C93 1.434(4) . ? C79 H79A 0.9800 . ? C79 H79B 0.9800 . ? C79 C67 1.508(4) . ? C35 C34 1.395(4) . ? C35 C40 1.524(4) . ? C35 C36A 1.429(6) . ? C35 C36B 1.350(15) . ? C48 H48 0.9400 . ? C48 C49 1.396(4) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 C5 1.506(3) . ? C67 C68 1.396(4) . ? C67 C72 1.403(4) . ? C68 C73 1.520(4) . ? C68 C69B 1.442(6) . ? C68 C69A 1.32(2) . ? C14 C15 1.377(4) . ? C14 C19 1.391(4) . ? C61 C66 1.373(4) . ? C61 C62 1.383(4) . ? C5 C6 1.401(3) . ? C5 C4 1.402(3) . ? C87 C92 1.381(4) . ? C87 C88 1.388(4) . ? C29 H29 0.9400 . ? C29 C30 1.399(4) . ? C34 C39 1.406(4) . ? C6 C11 1.511(3) . ? C6 C1 1.415(4) . ? C66 H66 0.9400 . ? C66 C65 1.392(4) . ? C85 H85 0.9400 . ? C85 C84 1.399(4) . ? C21 C26 1.384(4) . ? C21 C22 1.379(4) . ? C54 C55 1.385(4) . ? C54 C59 1.384(4) . ? C95 H95 0.9400 . ? C95 C94 1.380(4) . ? C95 C96 1.393(4) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 C41 1.525(4) . ? C49 H49 0.9400 . ? C49 C50 1.369(4) . ? C91 H91 0.9400 . ? C91 C90 1.380(5) . ? C91 C92 1.378(4) . ? C94 C99 1.378(4) . ? C81 H81 0.9400 . ? C81 C82 1.378(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 C12 1.526(4) . ? C26 H26 0.9400 . ? C26 C25 1.385(4) . ? C33 H33 0.9400 . ? C33 C32 1.380(4) . ? C96 H96 0.9400 . ? C96 C97 1.374(5) . ? C56 H56 0.9400 . ? C56 C57 1.377(4) . ? C56 C55 1.385(4) . ? C30 H30 0.9400 . ? C30 C31 1.370(4) . ? C72 C71B 1.452(6) . ? C72 C77 1.511(4) . ? C72 C71A 1.26(2) . ? C90 C89 1.368(5) . ? C25 H25 0.9400 . ? C25 C24 1.381(4) . ? C52 H52 0.9400 . ? C52 C51 1.369(4) . ? C73 H73A 0.9800 . ? C73 H73B 0.9800 . ? C73 C74 1.519(4) . ? C74 H74A 0.9700 . ? C74 H74B 0.9700 . ? C74 H74C 0.9700 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 C39 1.513(4) . ? C44 C45 1.531(4) . ? C64 C65 1.376(5) . ? C64 C63 1.374(5) . ? C98 H98 0.9400 . ? C98 C99 1.385(4) . ? C98 C97 1.368(5) . ? C92 H92 0.9400 . ? C65 H65 0.9400 . ? C83 C84 1.365(4) . ? C83 C82 1.378(4) . ? C57 C58 1.363(4) . ? C55 H55 0.9400 . ? C50 C51 1.382(4) . ? C1 C13 1.509(4) . ? C1 C2 1.400(4) . ? C84 H84 0.9400 . ? C15 H15 0.9400 . ? C15 C16 1.382(4) . ? C88 H88 0.9400 . ? C88 C89 1.365(5) . ? C32 H32 0.9400 . ? C32 C31 1.379(4) . ? C17 C18 1.380(4) . ? C17 C16 1.370(5) . ? C63 H63 0.9400 . ? C63 C62 1.379(4) . ? C99 H99 0.9400 . ? C24 C23 1.361(4) . ? C59 H59 0.9400 . ? C59 C58 1.367(4) . ? C69B C70B 1.408(6) . ? C69B C86 1.479(6) . ? C19 H19 0.9400 . ? C19 C18 1.374(4) . ? C36A C37A 1.398(6) . ? C36A C53 1.504(5) . ? C22 H22 0.9400 . ? C22 C23 1.391(4) . ? C39 C38A 1.444(6) . ? C39 C38B 1.317(17) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 C4 1.519(4) . ? C9 C10 1.524(4) . ? C71B C70B 1.387(6) . ? C71B C93 1.510(5) . ? C3 C20 1.507(4) . ? C3 C4 1.403(4) . ? C3 C2 1.403(4) . ? C62 H62 0.9400 . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C41 H41C 0.9700 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C82 H82 0.9400 . ? C89 H89 0.9400 . ? C23 H23 0.9400 . ? C58 H58 0.9400 . ? C18 H18 0.9400 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C45 H45C 0.9700 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C16 H16 0.9400 . ? C37A C38A 1.398(7) . ? C37A C42A 1.532(9) . ? C51 H51 0.9400 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C53 H53D 0.9800 . ? C53 C36B 1.616(15) . ? C70B C75B 1.523(7) . ? C77 H77A 0.9800 . ? C77 H77B 0.9800 . ? C77 C78 1.535(5) . ? C86 H86A 0.9800 . ? C86 H86B 0.9800 . ? C86 H86C 0.9800 . ? C86 H86D 0.9800 . ? C86 C69A 1.68(2) . ? C38A C60 1.500(5) . ? C78 H78A 0.9700 . ? C78 H78B 0.9700 . ? C78 H78C 0.9700 . ? C93 H93A 0.9800 . ? C93 H93B 0.9800 . ? C93 H93C 0.9800 . ? C93 H93D 0.9800 . ? C93 C71A 1.66(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C8 C7 1.526(4) . ? C2 C7 1.519(3) . ? C75B H75A 0.9800 . ? C75B H75B 0.9800 . ? C75B C76B 1.509(7) . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 0.9800 . ? C60 H60D 0.9800 . ? C60 C38B 1.649(18) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C43A H43A 0.9700 . ? C43A H43B 0.9700 . ? C43A H43C 0.9700 . ? C43A C42A 1.504(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C76B H76A 0.9700 . ? C76B H76B 0.9700 . ? C76B H76C 0.9700 . ? C42A H42A 0.9800 . ? C42A H42B 0.9800 . ? C75A H75C 0.9800 . ? C75A H75D 0.9800 . ? C75A C70A 1.51(2) . ? C75A C76A 1.56(3) . ? C37B C42B 1.50(2) . ? C37B C36B 1.40(2) . ? C37B C38B 1.41(2) . ? C42B H42C 0.9800 . ? C42B H42D 0.9800 . ? C42B C43B 1.58(3) . ? C70A C71A 1.47(3) . ? C70A C69A 1.39(3) . ? C76A H76D 0.9700 . ? C76A H76E 0.9700 . ? C76A H76F 0.9700 . ? C43B H43D 0.9700 . ? C43B H43E 0.9700 . ? C43B H43F 0.9700 . ? 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 O3 C27 117.3(2) . . ? C80 O9 C79 119.3(2) . . ? C47 O5 C46 119.6(2) . . ? C14 O1 C13 116.8(2) . . ? C87 O8 C86 116.2(2) . . ? O3 C28 C29 123.8(3) . . ? O3 C28 C33 116.2(2) . . ? C33 C28 C29 120.0(3) . . ? O9 C80 C85 123.9(3) . . ? O9 C80 C81 116.2(3) . . ? C81 C80 C85 119.9(3) . . ? C61 O4 C60 117.1(2) . . ? C21 O2 C20 117.9(2) . . ? O5 C47 C48 124.9(3) . . ? O5 C47 C52 115.4(2) . . ? C48 C47 C52 119.7(3) . . ? C54 O6 C53 117.2(2) . . ? O5 C46 H46A 110.8 . . ? O5 C46 H46B 110.8 . . ? O5 C46 C34 104.5(2) . . ? H46A C46 H46B 108.9 . . ? C34 C46 H46A 110.8 . . ? C34 C46 H46B 110.8 . . ? C94 O7 C93 116.0(2) . . ? O9 C79 H79A 110.7 . . ? O9 C79 H79B 110.7 . . ? O9 C79 C67 105.1(2) . . ? H79A C79 H79B 108.8 . . ? C67 C79 H79A 110.7 . . ? C67 C79 H79B 110.7 . . ? C34 C35 C40 120.8(2) . . ? C34 C35 C36A 119.7(3) . . ? C36A C35 C40 119.2(3) . . ? C36B C35 C34 117.7(7) . . ? C36B C35 C40 119.3(7) . . ? C36B C35 C36A 20.5(6) . . ? C47 C48 H48 120.3 . . ? C47 C48 C49 119.4(3) . . ? C49 C48 H48 120.3 . . ? O3 C27 H27A 110.3 . . ? O3 C27 H27B 110.3 . . ? O3 C27 C5 107.0(2) . . ? H27A C27 H27B 108.6 . . ? C5 C27 H27A 110.3 . . ? C5 C27 H27B 110.3 . . ? C68 C67 C79 118.8(2) . . ? C68 C67 C72 121.4(3) . . ? C72 C67 C79 119.6(3) . . ? C67 C68 C73 121.6(3) . . ? C67 C68 C69B 119.9(3) . . ? C69B C68 C73 118.4(3) . . ? C69A C68 C67 114.9(9) . . ? C69A C68 C73 121.0(9) . . ? C69A C68 C69B 19.5(8) . . ? O1 C14 C15 124.6(3) . . ? O1 C14 C19 115.9(2) . . ? C15 C14 C19 119.4(3) . . ? O4 C61 C66 124.4(3) . . ? O4 C61 C62 115.7(3) . . ? C66 C61 C62 119.9(3) . . ? C6 C5 C27 119.2(2) . . ? C6 C5 C4 120.7(2) . . ? C4 C5 C27 120.1(2) . . ? O8 C87 C92 124.6(3) . . ? O8 C87 C88 115.6(3) . . ? C92 C87 C88 119.8(3) . . ? C28 C29 H29 120.4 . . ? C28 C29 C30 119.1(3) . . ? C30 C29 H29 120.4 . . ? C35 C34 C46 119.5(2) . . ? C35 C34 C39 120.6(2) . . ? C39 C34 C46 119.7(2) . . ? C5 C6 C11 121.0(2) . . ? C5 C6 C1 119.2(2) . . ? C1 C6 C11 119.7(2) . . ? C61 C66 H66 120.2 . . ? C61 C66 C65 119.7(3) . . ? C65 C66 H66 120.2 . . ? C80 C85 H85 120.5 . . ? C80 C85 C84 118.9(3) . . ? C84 C85 H85 120.5 . . ? O2 C21 C26 115.1(2) . . ? O2 C21 C22 125.2(2) . . ? C22 C21 C26 119.7(3) . . ? O6 C54 C55 124.3(3) . . ? O6 C54 C59 115.8(3) . . ? C59 C54 C55 119.8(3) . . ? C94 C95 H95 120.1 . . ? C94 C95 C96 119.8(3) . . ? C96 C95 H95 120.1 . . ? C35 C40 H40A 109.0 . . ? C35 C40 H40B 109.0 . . ? C35 C40 C41 112.8(3) . . ? H40A C40 H40B 107.8 . . ? C41 C40 H40A 109.0 . . ? C41 C40 H40B 109.0 . . ? C48 C49 H49 120.1 . . ? C50 C49 C48 119.7(3) . . ? C50 C49 H49 120.1 . . ? C90 C91 H91 120.3 . . ? C92 C91 H91 120.3 . . ? C92 C91 C90 119.4(3) . . ? O7 C94 C95 124.0(3) . . ? O7 C94 C99 116.2(3) . . ? C99 C94 C95 119.8(3) . . ? C80 C81 H81 119.4 . . ? C82 C81 C80 121.2(3) . . ? C82 C81 H81 119.4 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? C6 C11 C12 110.8(2) . . ? H11A C11 H11B 108.1 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C21 C26 H26 119.9 . . ? C21 C26 C25 120.1(3) . . ? C25 C26 H26 119.9 . . ? C28 C33 H33 119.6 . . ? C32 C33 C28 120.8(3) . . ? C32 C33 H33 119.6 . . ? C95 C96 H96 120.1 . . ? C97 C96 C95 119.8(3) . . ? C97 C96 H96 120.1 . . ? C57 C56 H56 120.4 . . ? C57 C56 C55 119.2(3) . . ? C55 C56 H56 120.4 . . ? C29 C30 H30 120.0 . . ? C31 C30 C29 120.1(3) . . ? C31 C30 H30 120.0 . . ? C67 C72 C71B 117.8(3) . . ? C67 C72 C77 120.7(3) . . ? C71B C72 C77 121.5(3) . . ? C71A C72 C67 120.5(11) . . ? C71A C72 C71B 19.5(9) . . ? C71A C72 C77 115.4(10) . . ? C91 C90 Cl8 118.5(3) . . ? C89 C90 Cl8 120.5(3) . . ? C89 C90 C91 121.0(3) . . ? C26 C25 H25 120.2 . . ? C24 C25 C26 119.6(3) . . ? C24 C25 H25 120.2 . . ? C47 C52 H52 119.6 . . ? C51 C52 C47 120.7(3) . . ? C51 C52 H52 119.6 . . ? C68 C73 H73A 108.9 . . ? C68 C73 H73B 108.9 . . ? H73A C73 H73B 107.8 . . ? C74 C73 C68 113.2(3) . . ? C74 C73 H73A 108.9 . . ? C74 C73 H73B 108.9 . . ? C73 C74 H74A 109.5 . . ? C73 C74 H74B 109.5 . . ? C73 C74 H74C 109.5 . . ? H74A C74 H74B 109.5 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? H44A C44 H44B 108.0 . . ? C39 C44 H44A 109.4 . . ? C39 C44 H44B 109.4 . . ? C39 C44 C45 111.4(2) . . ? C45 C44 H44A 109.4 . . ? C45 C44 H44B 109.4 . . ? C65 C64 Cl4 119.6(3) . . ? C63 C64 Cl4 119.9(3) . . ? C63 C64 C65 120.4(3) . . ? C99 C98 H98 120.0 . . ? C97 C98 H98 120.0 . . ? C97 C98 C99 119.9(3) . . ? C87 C92 H92 120.1 . . ? C91 C92 C87 119.9(3) . . ? C91 C92 H92 120.1 . . ? C66 C65 H65 120.0 . . ? C64 C65 C66 120.0(3) . . ? C64 C65 H65 120.0 . . ? C84 C83 Cl9 119.4(2) . . ? C84 C83 C82 121.6(3) . . ? C82 C83 Cl9 119.0(3) . . ? C56 C57 Cl6 118.7(3) . . ? C58 C57 Cl6 120.6(3) . . ? C58 C57 C56 120.7(3) . . ? C54 C55 C56 119.9(3) . . ? C54 C55 H55 120.0 . . ? C56 C55 H55 120.0 . . ? C49 C50 Cl5 120.4(2) . . ? C49 C50 C51 121.2(3) . . ? C51 C50 Cl5 118.5(3) . . ? C6 C1 C13 118.3(2) . . ? C2 C1 C6 120.3(2) . . ? C2 C1 C13 121.4(2) . . ? C85 C84 H84 120.1 . . ? C83 C84 C85 119.9(3) . . ? C83 C84 H84 120.1 . . ? C14 C15 H15 120.0 . . ? C14 C15 C16 120.0(3) . . ? C16 C15 H15 120.0 . . ? C87 C88 H88 120.0 . . ? C89 C88 C87 120.1(3) . . ? C89 C88 H88 120.0 . . ? C33 C32 H32 120.5 . . ? C31 C32 C33 119.1(3) . . ? C31 C32 H32 120.5 . . ? C18 C17 Cl1 119.8(3) . . ? C16 C17 Cl1 119.7(3) . . ? C16 C17 C18 120.6(3) . . ? C64 C63 H63 120.2 . . ? C64 C63 C62 119.6(3) . . ? C62 C63 H63 120.2 . . ? C30 C31 Cl3 119.1(2) . . ? C30 C31 C32 120.9(3) . . ? C32 C31 Cl3 120.0(2) . . ? C94 C99 C98 120.2(3) . . ? C94 C99 H99 119.9 . . ? C98 C99 H99 119.9 . . ? C25 C24 Cl2 119.3(2) . . ? C23 C24 Cl2 120.2(2) . . ? C23 C24 C25 120.5(3) . . ? C54 C59 H59 120.2 . . ? C58 C59 C54 119.6(3) . . ? C58 C59 H59 120.2 . . ? C68 C69B C86 119.6(4) . . ? C70B C69B C68 119.3(4) . . ? C70B C69B C86 121.2(4) . . ? C14 C19 H19 119.8 . . ? C18 C19 C14 120.4(3) . . ? C18 C19 H19 119.8 . . ? C35 C36A C53 118.7(4) . . ? C37A C36A C35 120.4(4) . . ? C37A C36A C53 120.7(4) . . ? C21 C22 H22 120.1 . . ? C21 C22 C23 119.9(3) . . ? C23 C22 H22 120.1 . . ? C34 C39 C44 120.1(3) . . ? C34 C39 C38A 118.7(3) . . ? C38A C39 C44 121.2(3) . . ? C38B C39 C34 118.7(8) . . ? C38B C39 C44 118.5(8) . . ? C38B C39 C38A 19.2(7) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H9A C9 H9B 107.8 . . ? C4 C9 H9A 109.0 . . ? C4 C9 H9B 109.0 . . ? C4 C9 C10 112.8(2) . . ? C10 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C96 C97 Cl7 119.2(3) . . ? C98 C97 Cl7 120.3(3) . . ? C98 C97 C96 120.5(3) . . ? C72 C71B C93 117.9(4) . . ? C70B C71B C72 121.2(4) . . ? C70B C71B C93 120.9(4) . . ? C4 C3 C20 119.7(2) . . ? C4 C3 C2 120.4(2) . . ? C2 C3 C20 119.9(2) . . ? C61 C62 H62 119.8 . . ? C63 C62 C61 120.4(3) . . ? C63 C62 H62 119.8 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41B 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O1 C13 C1 107.5(2) . . ? O1 C13 H13A 110.2 . . ? O1 C13 H13B 110.2 . . ? C1 C13 H13A 110.2 . . ? C1 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? C81 C82 C83 118.5(3) . . ? C81 C82 H82 120.7 . . ? C83 C82 H82 120.7 . . ? C90 C89 H89 120.1 . . ? C88 C89 C90 119.9(3) . . ? C88 C89 H89 120.1 . . ? C24 C23 C22 120.2(3) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C57 C58 C59 120.8(3) . . ? C57 C58 H58 119.6 . . ? C59 C58 H58 119.6 . . ? C17 C18 H18 120.3 . . ? C19 C18 C17 119.4(3) . . ? C19 C18 H18 120.3 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45B 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O2 C20 C3 108.7(2) . . ? O2 C20 H20A 109.9 . . ? O2 C20 H20B 109.9 . . ? C3 C20 H20A 109.9 . . ? C3 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 120.0 . . ? C36A C37A C38A 119.7(4) . . ? C36A C37A C42A 119.3(4) . . ? C38A C37A C42A 121.0(4) . . ? C52 C51 C50 119.3(3) . . ? C52 C51 H51 120.4 . . ? C50 C51 H51 120.4 . . ? O6 C53 C36A 104.9(3) . . ? O6 C53 H53A 110.8 . . ? O6 C53 H53B 110.8 . . ? O6 C53 H53C 106.7 . . ? O6 C53 H53D 106.7 . . ? O6 C53 C36B 122.4(6) . . ? C36A C53 H53A 110.8 . . ? C36A C53 H53B 110.8 . . ? C36A C53 H53C 111.3 . . ? C36A C53 H53D 119.8 . . ? C36A C53 C36B 18.0(5) . . ? H53A C53 H53B 108.8 . . ? H53A C53 H53C 4.2 . . ? H53A C53 H53D 103.8 . . ? H53B C53 H53C 112.1 . . ? H53B C53 H53D 9.0 . . ? H53C C53 H53D 106.6 . . ? C36B C53 H53A 104.9 . . ? C36B C53 H53B 98.0 . . ? C36B C53 H53C 106.7 . . ? C36B C53 H53D 106.7 . . ? C5 C4 C9 119.8(2) . . ? C5 C4 C3 119.4(2) . . ? C3 C4 C9 120.8(2) . . ? C69B C70B C75B 119.0(4) . . ? C71B C70B C69B 120.1(4) . . ? C71B C70B C75B 120.8(4) . . ? C72 C77 H77A 109.3 . . ? C72 C77 H77B 109.3 . . ? C72 C77 C78 111.7(3) . . ? H77A C77 H77B 107.9 . . ? C78 C77 H77A 109.3 . . ? C78 C77 H77B 109.3 . . ? O8 C86 C69B 105.1(3) . . ? O8 C86 H86A 110.7 . . ? O8 C86 H86B 110.7 . . ? O8 C86 H86C 107.3 . . ? O8 C86 H86D 107.3 . . ? O8 C86 C69A 120.2(7) . . ? C69B C86 H86A 110.7 . . ? C69B C86 H86B 110.7 . . ? C69B C86 H86C 120.0 . . ? C69B C86 H86D 109.6 . . ? C69B C86 C69A 16.0(7) . . ? H86A C86 H86B 108.8 . . ? H86A C86 H86C 9.3 . . ? H86A C86 H86D 113.0 . . ? H86B C86 H86C 102.9 . . ? H86B C86 H86D 4.4 . . ? H86C C86 H86D 106.9 . . ? C69A C86 H86A 98.3 . . ? C69A C86 H86B 107.1 . . ? C69A C86 H86C 107.3 . . ? C69A C86 H86D 107.3 . . ? C39 C38A C60 118.7(4) . . ? C37A C38A C39 120.3(4) . . ? C37A C38A C60 120.9(4) . . ? C77 C78 H78A 109.5 . . ? C77 C78 H78B 109.5 . . ? C77 C78 H78C 109.5 . . ? H78A C78 H78B 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? O7 C93 C71B 112.5(3) . . ? O7 C93 H93A 109.1 . . ? O7 C93 H93B 109.1 . . ? O7 C93 H93C 112.6 . . ? O7 C93 H93D 112.6 . . ? O7 C93 C71A 95.7(7) . . ? C71B C93 H93A 109.1 . . ? C71B C93 H93B 109.1 . . ? C71B C93 H93C 107.1 . . ? C71B C93 H93D 101.2 . . ? C71B C93 C71A 17.2(7) . . ? H93A C93 H93B 107.8 . . ? H93A C93 H93C 3.5 . . ? H93A C93 H93D 112.2 . . ? H93B C93 H93C 106.2 . . ? H93B C93 H93D 8.0 . . ? H93C C93 H93D 110.1 . . ? C71A C93 H93A 113.6 . . ? C71A C93 H93B 120.5 . . ? C71A C93 H93C 112.6 . . ? C71A C93 H93D 112.6 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? C1 C2 C3 119.7(2) . . ? C1 C2 C7 119.9(2) . . ? C3 C2 C7 120.4(2) . . ? C70B C75B H75A 109.3 . . ? C70B C75B H75B 109.3 . . ? H75A C75B H75B 108.0 . . ? C76B C75B C70B 111.6(5) . . ? C76B C75B H75A 109.3 . . ? C76B C75B H75B 109.3 . . ? O4 C60 C38A 111.4(3) . . ? O4 C60 H60A 109.3 . . ? O4 C60 H60B 109.3 . . ? O4 C60 H60C 112.8 . . ? O4 C60 H60D 112.8 . . ? O4 C60 C38B 94.8(7) . . ? C38A C60 H60A 109.3 . . ? C38A C60 H60B 109.3 . . ? C38A C60 H60C 104.7 . . ? C38A C60 H60D 104.4 . . ? C38A C60 C38B 16.6(6) . . ? H60A C60 H60B 108.0 . . ? H60A C60 H60C 4.8 . . ? H60A C60 H60D 109.5 . . ? H60B C60 H60C 109.2 . . ? H60B C60 H60D 5.1 . . ? H60C C60 H60D 110.2 . . ? C38B C60 H60A 117.0 . . ? C38B C60 H60B 117.3 . . ? C38B C60 H60C 112.8 . . ? C38B C60 H60D 112.8 . . ? C8 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C2 C7 C8 112.1(2) . . ? C2 C7 H7A 109.2 . . ? C2 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C37A C42A H42A 109.2 . . ? C37A C42A H42B 109.2 . . ? C43A C42A C37A 112.2(7) . . ? C43A C42A H42A 109.2 . . ? C43A C42A H42B 109.2 . . ? H42A C42A H42B 107.9 . . ? H75C C75A H75D 107.6 . . ? C70A C75A H75C 108.7 . . ? C70A C75A H75D 108.7 . . ? C70A C75A C76A 114.1(18) . . ? C76A C75A H75C 108.7 . . ? C76A C75A H75D 108.7 . . ? C36B C37B C42B 121.0(13) . . ? C36B C37B C38B 118.1(13) . . ? C38B C37B C42B 120.9(14) . . ? C37B C42B H42C 108.8 . . ? C37B C42B H42D 108.8 . . ? C37B C42B C43B 114(2) . . ? H42C C42B H42D 107.7 . . ? C43B C42B H42C 108.8 . . ? C43B C42B H42D 108.8 . . ? C71A C70A C75A 120.1(15) . . ? C69A C70A C75A 124.7(15) . . ? C69A C70A C71A 115.2(16) . . ? C42B C43B H43D 109.5 . . ? C42B C43B H43E 109.5 . . ? C42B C43B H43F 109.5 . . ? H43D C43B H43E 109.5 . . ? H43D C43B H43F 109.5 . . ? H43E C43B H43F 109.5 . . ? C35 C36B C53 116.3(10) . . ? C35 C36B C37B 121.0(12) . . ? C37B C36B C53 116.6(11) . . ? C39 C38B C60 116.9(12) . . ? C39 C38B C37B 121.8(14) . . ? C37B C38B C60 116.0(12) . . ? C72 C71A C93 120.5(16) . . ? C72 C71A C70A 120.4(18) . . ? C70A C71A C93 112.7(14) . . ? C68 C69A C86 114.4(13) . . ? C68 C69A C70A 125.1(17) . . ? C70A C69A C86 115.7(14) . . ? 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 Cl4 C64 C65 C66 -178.4(2) . . . . ? Cl4 C64 C63 C62 179.0(3) . . . . ? Cl2 C24 C23 C22 177.4(2) . . . . ? Cl9 C83 C84 C85 -179.9(2) . . . . ? Cl9 C83 C82 C81 179.6(2) . . . . ? Cl5 C50 C51 C52 -180.0(2) . . . . ? Cl1 C17 C18 C19 -179.0(2) . . . . ? Cl1 C17 C16 C15 179.3(3) . . . . ? Cl6 C57 C58 C59 179.1(2) . . . . ? Cl8 C90 C89 C88 180.0(3) . . . . ? O3 C28 C29 C30 179.9(3) . . . . ? O3 C28 C33 C32 -179.9(3) . . . . ? O3 C27 C5 C6 -82.7(3) . . . . ? O3 C27 C5 C4 96.1(3) . . . . ? O9 C80 C85 C84 179.4(3) . . . . ? O9 C80 C81 C82 -179.7(3) . . . . ? O9 C79 C67 C68 83.4(3) . . . . ? O9 C79 C67 C72 -90.8(3) . . . . ? O5 C47 C48 C49 -179.7(3) . . . . ? O5 C47 C52 C51 179.4(3) . . . . ? O5 C46 C34 C35 -84.8(3) . . . . ? O5 C46 C34 C39 89.9(3) . . . . ? O1 C14 C15 C16 179.5(3) . . . . ? O1 C14 C19 C18 -179.3(3) . . . . ? O8 C87 C92 C91 -179.8(3) . . . . ? O8 C87 C88 C89 179.7(3) . . . . ? O8 C86 C69A C68 -58.5(15) . . . . ? O8 C86 C69A C70A 98.3(14) . . . . ? C28 O3 C27 C5 180.0(2) . . . . ? C28 C29 C30 C31 0.3(4) . . . . ? C28 C33 C32 C31 -0.3(5) . . . . ? C80 O9 C79 C67 -174.7(2) . . . . ? C80 C85 C84 C83 0.1(4) . . . . ? C80 C81 C82 C83 0.5(5) . . . . ? O4 C61 C66 C65 -178.8(3) . . . . ? O4 C61 C62 C63 179.6(3) . . . . ? O4 C60 C38B C39 96.7(12) . . . . ? O4 C60 C38B C37B -108.6(12) . . . . ? O2 C21 C26 C25 177.5(3) . . . . ? O2 C21 C22 C23 -176.8(2) . . . . ? C47 O5 C46 C34 174.1(2) . . . . ? C47 C48 C49 C50 0.7(4) . . . . ? C47 C52 C51 C50 0.0(5) . . . . ? O6 C54 C55 C56 178.0(3) . . . . ? O6 C54 C59 C58 -178.2(3) . . . . ? O6 C53 C36B C35 61.3(13) . . . . ? O6 C53 C36B C37B -91.6(12) . . . . ? C46 O5 C47 C48 4.1(4) . . . . ? C46 O5 C47 C52 -175.4(3) . . . . ? C46 C34 C39 C44 11.2(4) . . . . ? C46 C34 C39 C38A -166.0(4) . . . . ? C46 C34 C39 C38B 172.0(9) . . . . ? O7 C94 C99 C98 -179.8(3) . . . . ? O7 C93 C71A C72 -101.6(15) . . . . ? O7 C93 C71A C70A 106.2(13) . . . . ? C79 O9 C80 C85 -2.0(4) . . . . ? C79 O9 C80 C81 177.7(3) . . . . ? C79 C67 C68 C73 4.9(4) . . . . ? C79 C67 C68 C69B -171.7(4) . . . . ? C79 C67 C68 C69A 167.1(9) . . . . ? C79 C67 C72 C71B 167.9(3) . . . . ? C79 C67 C72 C77 -11.5(4) . . . . ? C79 C67 C72 C71A -170.0(11) . . . . ? C35 C34 C39 C44 -174.1(3) . . . . ? C35 C34 C39 C38A 8.6(5) . . . . ? C35 C34 C39 C38B -13.4(10) . . . . ? C35 C36A C37A C38A 4.5(7) . . . . ? C35 C36A C37A C42A -175.9(5) . . . . ? C35 C36A C53 O6 96.3(5) . . . . ? C35 C36A C53 C36B -70(2) . . . . ? C48 C47 C52 C51 -0.1(5) . . . . ? C48 C49 C50 Cl5 179.6(2) . . . . ? C48 C49 C50 C51 -0.9(4) . . . . ? C27 O3 C28 C29 5.4(4) . . . . ? C27 O3 C28 C33 -175.3(2) . . . . ? C27 C5 C6 C11 -6.1(4) . . . . ? C27 C5 C6 C1 178.0(2) . . . . ? C27 C5 C4 C9 0.7(4) . . . . ? C27 C5 C4 C3 177.5(2) . . . . ? C67 C68 C73 C74 90.1(4) . . . . ? C67 C68 C69B C70B 3.0(6) . . . . ? C67 C68 C69B C86 -175.5(4) . . . . ? C67 C68 C69A C86 166.5(8) . . . . ? C67 C68 C69A C70A 12.3(19) . . . . ? C67 C72 C71B C70B 4.7(6) . . . . ? C67 C72 C71B C93 -174.8(3) . . . . ? C67 C72 C77 C78 -80.5(4) . . . . ? C67 C72 C71A C93 -155.2(10) . . . . ? C67 C72 C71A C70A -5(2) . . . . ? C68 C67 C72 C71B -6.1(5) . . . . ? C68 C67 C72 C77 174.5(3) . . . . ? C68 C67 C72 C71A 16.0(12) . . . . ? C68 C69B C70B C71B -4.5(7) . . . . ? C68 C69B C70B C75B 175.1(4) . . . . ? C68 C69B C86 O8 -90.1(5) . . . . ? C68 C69B C86 C69A 71(3) . . . . ? C14 O1 C13 C1 -167.0(2) . . . . ? C14 C15 C16 C17 -0.1(5) . . . . ? C14 C19 C18 C17 -0.5(5) . . . . ? C61 O4 C60 C38A 178.9(3) . . . . ? C61 O4 C60 C38B 178.7(6) . . . . ? C61 C66 C65 C64 -0.2(5) . . . . ? C5 C6 C11 C12 -89.0(3) . . . . ? C5 C6 C1 C13 -177.5(2) . . . . ? C5 C6 C1 C2 2.7(4) . . . . ? C87 O8 C86 C69B 174.0(3) . . . . ? C87 O8 C86 C69A 168.0(8) . . . . ? C87 C88 C89 C90 -0.1(5) . . . . ? C29 C28 C33 C32 -0.6(5) . . . . ? C29 C30 C31 Cl3 178.6(2) . . . . ? C29 C30 C31 C32 -1.3(4) . . . . ? C34 C35 C40 C41 -90.4(3) . . . . ? C34 C35 C36A C37A -0.8(6) . . . . ? C34 C35 C36A C53 173.8(4) . . . . ? C34 C35 C36B C53 -165.9(7) . . . . ? C34 C35 C36B C37B -14.2(15) . . . . ? C34 C39 C38A C37A -4.9(6) . . . . ? C34 C39 C38A C60 177.3(4) . . . . ? C34 C39 C38B C60 158.8(8) . . . . ? C34 C39 C38B C37B 5.8(17) . . . . ? C6 C5 C4 C9 179.5(2) . . . . ? C6 C5 C4 C3 -3.8(4) . . . . ? C6 C1 C13 O1 72.6(3) . . . . ? C6 C1 C2 C3 0.0(4) . . . . ? C6 C1 C2 C7 179.6(2) . . . . ? C66 C61 C62 C63 0.9(5) . . . . ? C85 C80 C81 C82 0.0(5) . . . . ? C21 O2 C20 C3 177.5(2) . . . . ? C21 C26 C25 C24 0.1(5) . . . . ? C21 C22 C23 C24 -1.3(4) . . . . ? C54 O6 C53 C36A -177.5(3) . . . . ? C54 O6 C53 C36B -172.6(7) . . . . ? C54 C59 C58 C57 -0.2(5) . . . . ? C95 C94 C99 C98 -0.5(5) . . . . ? C95 C96 C97 Cl7 178.4(2) . . . . ? C95 C96 C97 C98 -1.1(5) . . . . ? C40 C35 C34 C46 -4.8(4) . . . . ? C40 C35 C34 C39 -179.4(3) . . . . ? C40 C35 C36A C37A 172.9(4) . . . . ? C40 C35 C36A C53 -12.5(6) . . . . ? C40 C35 C36B C53 30.8(14) . . . . ? C40 C35 C36B C37B -177.6(10) . . . . ? C49 C50 C51 C52 0.5(5) . . . . ? C91 C90 C89 C88 -0.2(5) . . . . ? C94 O7 C93 C71B 177.5(3) . . . . ? C94 O7 C93 C71A 173.7(8) . . . . ? C94 C95 C96 C97 0.9(5) . . . . ? C81 C80 C85 C84 -0.3(4) . . . . ? C11 C6 C1 C13 6.5(4) . . . . ? C11 C6 C1 C2 -173.3(2) . . . . ? C26 C21 C22 C23 2.8(4) . . . . ? C26 C25 C24 Cl2 -176.8(2) . . . . ? C26 C25 C24 C23 1.4(5) . . . . ? C33 C28 C29 C30 0.6(4) . . . . ? C33 C32 C31 Cl3 -178.7(2) . . . . ? C33 C32 C31 C30 1.3(5) . . . . ? C96 C95 C94 O7 179.2(3) . . . . ? C96 C95 C94 C99 -0.1(5) . . . . ? C56 C57 C58 C59 0.3(5) . . . . ? C72 C67 C68 C73 179.0(3) . . . . ? C72 C67 C68 C69B 2.4(5) . . . . ? C72 C67 C68 C69A -18.8(10) . . . . ? C72 C71B C70B C69B 0.6(7) . . . . ? C72 C71B C70B C75B -178.9(4) . . . . ? C72 C71B C93 O7 -70.6(5) . . . . ? C72 C71B C93 C71A -58(3) . . . . ? C90 C91 C92 C87 0.6(6) . . . . ? C25 C24 C23 C22 -0.8(5) . . . . ? C52 C47 C48 C49 -0.2(4) . . . . ? C73 C68 C69B C70B -173.7(4) . . . . ? C73 C68 C69B C86 7.8(6) . . . . ? C73 C68 C69A C86 -31.2(16) . . . . ? C73 C68 C69A C70A 174.6(13) . . . . ? C44 C39 C38A C37A 177.9(4) . . . . ? C44 C39 C38A C60 0.1(6) . . . . ? C44 C39 C38B C60 -40.1(15) . . . . ? C44 C39 C38B C37B 166.8(11) . . . . ? C64 C63 C62 C61 -1.0(5) . . . . ? C92 C87 C88 C89 0.8(5) . . . . ? C92 C91 C90 Cl8 179.8(3) . . . . ? C92 C91 C90 C89 0.0(6) . . . . ? C65 C64 C63 C62 0.6(5) . . . . ? C57 C56 C55 C54 0.3(5) . . . . ? C55 C54 C59 C58 0.0(4) . . . . ? C55 C56 C57 Cl6 -179.2(2) . . . . ? C55 C56 C57 C58 -0.4(5) . . . . ? C1 C6 C11 C12 86.8(3) . . . . ? C1 C2 C7 C8 78.3(3) . . . . ? C84 C83 C82 C81 -0.8(5) . . . . ? C15 C14 C19 C18 -0.3(5) . . . . ? C88 C87 C92 C91 -1.0(5) . . . . ? C63 C64 C65 C66 0.1(5) . . . . ? C99 C98 C97 Cl7 -179.0(2) . . . . ? C99 C98 C97 C96 0.5(5) . . . . ? C59 C54 C55 C56 -0.1(5) . . . . ? C69B C68 C73 C74 -93.2(4) . . . . ? C69B C68 C69A C86 57(3) . . . . ? C69B C68 C69A C70A -97(4) . . . . ? C69B C70B C75B C76B 100.9(5) . . . . ? C69B C86 C69A C68 -80(3) . . . . ? C69B C86 C69A C70A 77(3) . . . . ? C19 C14 C15 C16 0.5(5) . . . . ? C36A C35 C34 C46 168.8(4) . . . . ? C36A C35 C34 C39 -5.9(5) . . . . ? C36A C35 C40 C41 96.0(4) . . . . ? C36A C35 C36B C53 -64.8(19) . . . . ? C36A C35 C36B C37B 87(2) . . . . ? C36A C37A C38A C39 -1.6(7) . . . . ? C36A C37A C38A C60 176.1(5) . . . . ? C36A C37A C42A C43A -99.6(5) . . . . ? C36A C53 C36B C35 77(2) . . . . ? C36A C53 C36B C37B -76(2) . . . . ? C22 C21 C26 C25 -2.2(4) . . . . ? C39 C38A C60 O4 66.2(5) . . . . ? C39 C38A C60 C38B 67(2) . . . . ? C97 C98 C99 C94 0.3(5) . . . . ? C71B C72 C77 C78 100.1(4) . . . . ? C71B C72 C71A C93 -68(3) . . . . ? C71B C72 C71A C70A 82(3) . . . . ? C71B C70B C75B C76B -79.6(5) . . . . ? C71B C93 C71A C72 90(3) . . . . ? C71B C93 C71A C70A -62(3) . . . . ? C3 C2 C7 C8 -102.1(3) . . . . ? C62 C61 C66 C65 -0.2(5) . . . . ? C13 O1 C14 C15 -10.5(4) . . . . ? C13 O1 C14 C19 168.5(2) . . . . ? C13 C1 C2 C3 -179.8(2) . . . . ? C13 C1 C2 C7 -0.2(4) . . . . ? C82 C83 C84 C85 0.4(5) . . . . ? C18 C17 C16 C15 -0.6(5) . . . . ? C45 C44 C39 C34 78.6(4) . . . . ? C45 C44 C39 C38A -104.2(4) . . . . ? C45 C44 C39 C38B -82.2(10) . . . . ? C20 O2 C21 C26 176.9(2) . . . . ? C20 O2 C21 C22 -3.5(4) . . . . ? C20 C3 C4 C5 -173.1(2) . . . . ? C20 C3 C4 C9 3.6(4) . . . . ? C20 C3 C2 C1 175.0(2) . . . . ? C20 C3 C2 C7 -4.6(4) . . . . ? C16 C17 C18 C19 0.9(5) . . . . ? C37A C36A C53 O6 -89.1(5) . . . . ? C37A C36A C53 C36B 104(2) . . . . ? C37A C38A C60 O4 -111.6(4) . . . . ? C37A C38A C60 C38B -111(3) . . . . ? C53 O6 C54 C55 -7.2(4) . . . . ? C53 O6 C54 C59 170.9(3) . . . . ? C53 C36A C37A C38A -170.1(5) . . . . ? C53 C36A C37A C42A 9.5(7) . . . . ? C4 C5 C6 C11 175.1(2) . . . . ? C4 C5 C6 C1 -0.8(4) . . . . ? C4 C3 C20 O2 -112.1(3) . . . . ? C4 C3 C2 C1 -4.6(4) . . . . ? C4 C3 C2 C7 175.8(2) . . . . ? C70B C69B C86 O8 91.4(5) . . . . ? C70B C69B C86 C69A -108(3) . . . . ? C70B C71B C93 O7 110.0(5) . . . . ? C70B C71B C93 C71A 123(3) . . . . ? C77 C72 C71B C70B -176.0(4) . . . . ? C77 C72 C71B C93 4.6(6) . . . . ? C77 C72 C71A C93 45.2(17) . . . . ? C77 C72 C71A C70A -164.8(13) . . . . ? C86 O8 C87 C92 13.1(4) . . . . ? C86 O8 C87 C88 -165.8(3) . . . . ? C86 C69B C70B C71B 174.0(5) . . . . ? C86 C69B C70B C75B -6.4(7) . . . . ? C38A C39 C38B C60 63(2) . . . . ? C38A C39 C38B C37B -90(3) . . . . ? C38A C37A C42A C43A 80.0(6) . . . . ? C38A C60 C38B C39 -83(3) . . . . ? C38A C60 C38B C37B 72(2) . . . . ? C93 O7 C94 C95 19.6(4) . . . . ? C93 O7 C94 C99 -161.1(3) . . . . ? C93 C71B C70B C69B -180.0(4) . . . . ? C93 C71B C70B C75B 0.5(7) . . . . ? C2 C1 C13 O1 -107.6(3) . . . . ? C2 C3 C20 O2 68.3(3) . . . . ? C2 C3 C4 C5 6.5(4) . . . . ? C2 C3 C4 C9 -176.9(2) . . . . ? C60 O4 C61 C66 -21.8(4) . . . . ? C60 O4 C61 C62 159.6(3) . . . . ? C10 C9 C4 C5 86.3(3) . . . . ? C10 C9 C4 C3 -90.4(3) . . . . ? C42A C37A C38A C39 178.8(5) . . . . ? C42A C37A C38A C60 -3.4(7) . . . . ? C75A C70A C71A C72 177.5(17) . . . . ? C75A C70A C71A C93 -30(2) . . . . ? C75A C70A C69A C68 178.5(17) . . . . ? C75A C70A C69A C86 25(2) . . . . ? C42B C37B C36B C35 -175.6(18) . . . . ? C42B C37B C36B C53 -24(2) . . . . ? C42B C37B C38B C39 180.0(18) . . . . ? C42B C37B C38B C60 27(2) . . . . ? C76A C75A C70A C71A 99.4(18) . . . . ? C76A C75A C70A C69A -82(2) . . . . ? C36B C35 C34 C46 -167.9(8) . . . . ? C36B C35 C34 C39 17.5(9) . . . . ? C36B C35 C40 C41 72.4(9) . . . . ? C36B C35 C36A C37A -91(2) . . . . ? C36B C35 C36A C53 84(2) . . . . ? C36B C37B C42B C43B 85.0(19) . . . . ? C36B C37B C38B C39 -3(2) . . . . ? C36B C37B C38B C60 -155.9(14) . . . . ? C38B C39 C38A C37A 90(3) . . . . ? C38B C39 C38A C60 -87(3) . . . . ? C38B C37B C42B C43B -97.7(19) . . . . ? C38B C37B C36B C35 7(2) . . . . ? C38B C37B C36B C53 158.5(14) . . . . ? C71A C72 C71B C70B -99(4) . . . . ? C71A C72 C71B C93 82(3) . . . . ? C71A C72 C77 C78 79.0(11) . . . . ? C71A C70A C69A C68 -3(2) . . . . ? C71A C70A C69A C86 -156.5(14) . . . . ? C69A C68 C73 C74 -71.0(10) . . . . ? C69A C68 C69B C70B 83(3) . . . . ? C69A C68 C69B C86 -95(3) . . . . ? C69A C70A C71A C72 -1(2) . . . . ? C69A C70A C71A C93 150.7(15) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962408' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-gf-262K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-gf, 262 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Cl3 O3' _chemical_formula_sum 'C33 H33 Cl3 O3' _chemical_formula_weight 583.94 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/a 1' _space_group_name_Hall '-P 2yab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z' _cell_length_a 24.9516(10) _cell_length_b 13.4628(4) _cell_length_c 28.8673(11) _cell_angle_alpha 90.00 _cell_angle_beta 110.600(4) _cell_angle_gamma 90.00 _cell_volume 9077.0(6) _cell_formula_units_Z 12 _cell_measurement_reflns_used 8513 _cell_measurement_temperature 262(2) _cell_measurement_theta_max 29.1148 _cell_measurement_theta_min 4.0434 _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92447 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 3672 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_unetI/netI 0.1137 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 57490 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.18 _diffrn_reflns_theta_min 4.05 _diffrn_ambient_temperature 262(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.866 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0026214000 _diffrn_orient_matrix_UB_12 0.0504755000 _diffrn_orient_matrix_UB_13 -0.0059133000 _diffrn_orient_matrix_UB_21 -0.0272020000 _diffrn_orient_matrix_UB_22 -0.0024039000 _diffrn_orient_matrix_UB_23 -0.0191448000 _diffrn_orient_matrix_UB_31 -0.0132589000 _diffrn_orient_matrix_UB_32 0.0148896000 _diffrn_orient_matrix_UB_33 0.0169532000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 9112 _reflns_number_total 21259 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.385 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef 0.00058(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 1123 _refine_ls_number_reflns 21259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1769 _refine_ls_R_factor_gt 0.0753 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1627 _refine_ls_wR_factor_ref 0.2145 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Sof(H86C)=Sof(H86D)=Sof(H93C)=Sof(H93D)=Sof(C75A)=Sof(H75C)=Sof(H75D)= Sof(C70A)=Sof(C76A)=Sof(H76D)=Sof(H76E)=Sof(H76F)=Sof(C71A)=Sof(C69A)=1-FVAR(1) Sof(C69B)=Sof(C71B)=Sof(C70B)=Sof(H86A)=Sof(H86B)=Sof(H93A)=Sof(H93B)= Sof(C75B)=Sof(H75A)=Sof(H75B)=Sof(C76B)=Sof(H76A)=Sof(H76B)=Sof(H76C)=FVAR(1) Sof(H53C)=Sof(H53D)=Sof(H60C)=Sof(H60D)=Sof(C37B)=Sof(C42B)=Sof(H42C)= Sof(H42D)=Sof(C43B)=Sof(H43D)=Sof(H43E)=Sof(H43F)=Sof(C36B)=Sof(C38B)=1-FVAR(2) Sof(C36A)=Sof(C37A)=Sof(H53A)=Sof(H53B)=Sof(C38A)=Sof(H60A)=Sof(H60B)= Sof(C43A)=Sof(H43A)=Sof(H43B)=Sof(H43C)=Sof(C42A)=Sof(H42A)=Sof(H42B)=FVAR(2) 3.a Secondary CH2 refined with riding coordinates: C46(H46A,H46B), C79(H79A,H79B), C27(H27A,H27B), C40(H40A,H40B), C11(H11A, H11B), C73(H73A,H73B), C44(H44A,H44B), C9(H9A,H9B), C13(H13A,H13B), C20(H20A, H20B), C53(H53A,H53B), C53(H53C,H53D), C77(H77A,H77B), C86(H86A,H86B), C86(H86C,H86D), C93(H93A,H93B), C93(H93C,H93D), C75B(H75A,H75B), C60(H60A, H60B), C60(H60C,H60D), C7(H7A,H7B), C42A(H42A,H42B), C75A(H75C,H75D), C42B(H42C,H42D) 3.b Aromatic/amide H refined with riding coordinates: C48(H48), C29(H29), C66(H66), C85(H85), C95(H95), C49(H49), C91(H91), C81(H81), C26(H26), C33(H33), C96(H96), C56(H56), C30(H30), C25(H25), C52(H52), C98(H98), C92(H92), C65(H65), C55(H55), C84(H84), C15(H15), C88(H88), C32(H32), C63(H63), C99(H99), C59(H59), C19(H19), C22(H22), C62(H62), C82(H82), C89(H89), C23(H23), C58(H58), C18(H18), C16(H16), C51(H51) 3.c Idealised Me refined as rotating group: C74(H74A,H74B,H74C), C12(H12A,H12B,H12C), C41(H41A,H41B,H41C), C45(H45A,H45B, H45C), C78(H78A,H78B,H78C), C8(H8A,H8B,H8C), C43A(H43A,H43B,H43C), C10(H10A, H10B,H10C), C76B(H76A,H76B,H76C), C76A(H76D,H76E,H76F), C43B(H43D,H43E,H43F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl4 Cl 0.39878(8) 0.00632(8) 0.14628(4) 0.1212(6) Uani 1 1 d . . . Cl2 Cl 0.40978(6) 0.00680(7) 0.48381(4) 0.0867(4) Uani 1 1 d . . . Cl7 Cl 0.60691(7) 0.99783(8) 0.18899(4) 0.1117(5) Uani 1 1 d . . . Cl9 Cl 0.71874(5) 0.18289(9) -0.18268(4) 0.0820(4) Uani 1 1 d . . . Cl3 Cl 0.28715(5) 0.81585(8) 0.85849(4) 0.0753(3) Uani 1 1 d . . . Cl5 Cl 0.26551(5) 0.84847(8) 0.50517(4) 0.0803(4) Uani 1 1 d . . . Cl1 Cl 0.77284(5) 1.03307(9) 0.72815(5) 0.0954(4) Uani 1 1 d . . . Cl6 Cl 0.78408(5) 1.04906(10) 0.39133(5) 0.0955(4) Uani 1 1 d . . . Cl8 Cl 0.21908(6) -0.05704(11) -0.05910(5) 0.1064(4) Uani 1 1 d . . . O3 O 0.38752(9) 0.70882(17) 0.70931(7) 0.0492(6) Uani 1 1 d . . . O9 O 0.60883(10) 0.30628(18) -0.04284(8) 0.0580(6) Uani 1 1 d . . . O5 O 0.38164(10) 0.70710(18) 0.37296(8) 0.0569(6) Uani 1 1 d . . . O1 O 0.57365(9) 0.76744(17) 0.65788(8) 0.0509(6) Uani 1 1 d . . . O8 O 0.41031(12) 0.22440(18) -0.00505(10) 0.0654(7) Uani 1 1 d A . . C28 C 0.36114(13) 0.7353(2) 0.74215(11) 0.0400(7) Uani 1 1 d . . . C80 C 0.63753(14) 0.2753(2) -0.07289(12) 0.0446(8) Uani 1 1 d . . . O4 O 0.41996(10) 0.41372(17) 0.22288(9) 0.0598(6) Uani 1 1 d B . . O2 O 0.43965(9) 0.41082(16) 0.56582(8) 0.0515(6) Uani 1 1 d . . . C47 C 0.35109(13) 0.7419(2) 0.40081(12) 0.0431(8) Uani 1 1 d . . . O6 O 0.58721(11) 0.78042(18) 0.34197(10) 0.0633(7) Uani 1 1 d B . . C46 C 0.35934(13) 0.7224(3) 0.31978(11) 0.0467(8) Uani 1 1 d . . . H46A H 0.3518 0.7922 0.3118 0.056 Uiso 1 1 calc . . R H46B H 0.3243 0.6850 0.3044 0.056 Uiso 1 1 calc . . R O7 O 0.58043(11) 0.58503(17) 0.11981(9) 0.0594(6) Uani 1 1 d A . . C79 C 0.63375(15) 0.2863(3) 0.00967(11) 0.0504(8) Uani 1 1 d . . . H79A H 0.6691 0.3230 0.0244 0.060 Uiso 1 1 calc . . R H79B H 0.6416 0.2160 0.0157 0.060 Uiso 1 1 calc . . R C35 C 0.45121(14) 0.7473(2) 0.30477(11) 0.0425(7) Uani 1 1 d . . . C48 C 0.29775(13) 0.7862(2) 0.38189(12) 0.0462(8) Uani 1 1 d . . . H48 H 0.2798 0.7939 0.3479 0.055 Uiso 1 1 calc . . R C27 C 0.36021(13) 0.7383(2) 0.65852(11) 0.0424(7) Uani 1 1 d . . . H27A H 0.3570 0.8100 0.6560 0.051 Uiso 1 1 calc . . R H27B H 0.3221 0.7099 0.6450 0.051 Uiso 1 1 calc . . R C67 C 0.58882(15) 0.3208(2) 0.03048(11) 0.0450(8) Uani 1 1 d A . . C68 C 0.54464(14) 0.2574(2) 0.02859(11) 0.0442(8) Uani 1 1 d . . . C14 C 0.61978(13) 0.8316(2) 0.67189(12) 0.0427(8) Uani 1 1 d . . . C61 C 0.41801(15) 0.3166(2) 0.20683(13) 0.0478(8) Uani 1 1 d . . . C5 C 0.39694(12) 0.7006(2) 0.63064(10) 0.0367(7) Uani 1 1 d . . . C87 C 0.36612(16) 0.1575(3) -0.01483(14) 0.0521(9) Uani 1 1 d . . . C29 C 0.30852(14) 0.7818(2) 0.72887(12) 0.0462(8) Uani 1 1 d . . . H29 H 0.2883 0.7972 0.6959 0.055 Uiso 1 1 calc . . R C34 C 0.40658(13) 0.6846(2) 0.30287(11) 0.0407(7) Uani 1 1 d B . . C6 C 0.44449(12) 0.7561(2) 0.63129(10) 0.0351(7) Uani 1 1 d . . . C66 C 0.46167(15) 0.2500(2) 0.22608(13) 0.0522(9) Uani 1 1 d . . . H66 H 0.4948 0.2686 0.2518 0.063 Uiso 1 1 calc . . R C85 C 0.69006(14) 0.2283(2) -0.05647(13) 0.0489(8) Uani 1 1 d . . . H85 H 0.7087 0.2156 -0.0230 0.059 Uiso 1 1 calc . . R C21 C 0.43037(13) 0.3196(2) 0.54302(11) 0.0376(7) Uani 1 1 d . . . C54 C 0.63300(15) 0.8426(2) 0.35049(13) 0.0473(8) Uani 1 1 d . . . C95 C 0.54172(15) 0.7518(2) 0.11372(12) 0.0536(9) Uani 1 1 d . . . H95 H 0.5085 0.7336 0.0880 0.064 Uiso 1 1 calc . . R C40 C 0.45116(15) 0.8558(2) 0.31966(12) 0.0487(8) Uani 1 1 d B . . H40A H 0.4313 0.8615 0.3430 0.058 Uiso 1 1 calc . . R H40B H 0.4904 0.8771 0.3363 0.058 Uiso 1 1 calc . . R C49 C 0.27104(14) 0.8193(2) 0.41403(14) 0.0512(9) Uani 1 1 d . . . H49 H 0.2351 0.8489 0.4017 0.061 Uiso 1 1 calc . . R C91 C 0.30823(19) 0.0371(3) 0.00651(15) 0.0764(12) Uani 1 1 d . . . H91 H 0.2997 0.0003 0.0303 0.092 Uiso 1 1 calc . . R C94 C 0.58370(15) 0.6824(2) 0.13433(12) 0.0470(8) Uani 1 1 d . . . C81 C 0.61043(16) 0.2937(3) -0.12278(13) 0.0593(10) Uani 1 1 d . . . H81 H 0.5749 0.3249 -0.1336 0.071 Uiso 1 1 calc . . R C11 C 0.45555(14) 0.8573(2) 0.65496(12) 0.0465(8) Uani 1 1 d . . . H11A H 0.4964 0.8700 0.6678 0.056 Uiso 1 1 calc . . R H11B H 0.4419 0.8590 0.6825 0.056 Uiso 1 1 calc . . R C26 C 0.47332(14) 0.2511(2) 0.56304(12) 0.0494(8) Uani 1 1 d . . . H26 H 0.5062 0.2690 0.5892 0.059 Uiso 1 1 calc . . R C33 C 0.39039(16) 0.7135(3) 0.79117(13) 0.0559(9) Uani 1 1 d . . . H33 H 0.4260 0.6830 0.8002 0.067 Uiso 1 1 calc . . R C96 C 0.54853(18) 0.8490(3) 0.13096(13) 0.0645(10) Uani 1 1 d . . . H96 H 0.5200 0.8958 0.1169 0.077 Uiso 1 1 calc . . R C56 C 0.69164(16) 0.9591(3) 0.32698(14) 0.0593(10) Uani 1 1 d . . . H56 H 0.6995 0.9955 0.3027 0.071 Uiso 1 1 calc . . R C30 C 0.28612(14) 0.8053(2) 0.76529(13) 0.0499(9) Uani 1 1 d . . . H30 H 0.2506 0.8362 0.7567 0.060 Uiso 1 1 calc . . R C72 C 0.59067(15) 0.4191(2) 0.04736(11) 0.0457(8) Uani 1 1 d . . . C90 C 0.27614(17) 0.0268(3) -0.04243(15) 0.0636(10) Uani 1 1 d . . . C25 C 0.46747(17) 0.1552(3) 0.54410(13) 0.0576(9) Uani 1 1 d . . . H25 H 0.4964 0.1088 0.5573 0.069 Uiso 1 1 calc . . R C52 C 0.37728(14) 0.7306(3) 0.45133(13) 0.0539(9) Uani 1 1 d . . . H52 H 0.4131 0.7006 0.4640 0.065 Uiso 1 1 calc . . R C73 C 0.54199(16) 0.1510(2) 0.00965(12) 0.0538(9) Uani 1 1 d A . . H73A H 0.5022 0.1317 -0.0057 0.065 Uiso 1 1 calc . . R H73B H 0.5593 0.1489 -0.0156 0.065 Uiso 1 1 calc . . R C74 C 0.57207(19) 0.0764(3) 0.04980(15) 0.0779(12) Uani 1 1 d . . . H74A H 0.5668 0.0107 0.0360 0.117 Uiso 1 1 calc A . GR H74B H 0.5562 0.0798 0.0756 0.117 Uiso 1 1 calc . . GR H74C H 0.6122 0.0915 0.0632 0.117 Uiso 1 1 calc . . GR C44 C 0.35552(14) 0.5190(3) 0.28310(13) 0.0525(9) Uani 1 1 d B . . H44A H 0.3411 0.5322 0.3096 0.063 Uiso 1 1 calc . . R H44B H 0.3670 0.4498 0.2853 0.063 Uiso 1 1 calc . . R C64 C 0.4069(2) 0.1272(3) 0.16921(13) 0.0651(11) Uani 1 1 d . . . C98 C 0.63956(17) 0.8070(3) 0.18939(14) 0.0647(11) Uani 1 1 d . . . H98 H 0.6729 0.8258 0.2148 0.078 Uiso 1 1 calc . . R C92 C 0.35355(18) 0.1029(3) 0.02032(14) 0.0687(11) Uani 1 1 d . . . H92 H 0.3757 0.1104 0.0536 0.082 Uiso 1 1 calc . . R C65 C 0.45608(18) 0.1540(3) 0.20673(13) 0.0641(10) Uani 1 1 d . . . H65 H 0.4857 0.1084 0.2193 0.077 Uiso 1 1 calc . . R C83 C 0.68716(15) 0.2189(3) -0.13996(14) 0.0508(9) Uani 1 1 d . . . C57 C 0.72612(14) 0.9675(3) 0.37579(14) 0.0565(9) Uani 1 1 d . . . C55 C 0.64494(15) 0.8956(3) 0.31440(13) 0.0560(9) Uani 1 1 d . . . H55 H 0.6215 0.8888 0.2814 0.067 Uiso 1 1 calc . . R C50 C 0.29838(15) 0.8076(2) 0.46419(14) 0.0499(9) Uani 1 1 d . . . C1 C 0.47957(12) 0.7201(2) 0.60612(11) 0.0381(7) Uani 1 1 d . . . C84 C 0.71480(15) 0.2001(2) -0.09110(14) 0.0533(9) Uani 1 1 d . . . H84 H 0.7502 0.1685 -0.0807 0.064 Uiso 1 1 calc . . R C15 C 0.63329(16) 0.8933(3) 0.64000(13) 0.0569(10) Uani 1 1 d . . . H15 H 0.6109 0.8932 0.6066 0.068 Uiso 1 1 calc . . R C88 C 0.33308(17) 0.1443(3) -0.06430(14) 0.0616(10) Uani 1 1 d . . . H88 H 0.3416 0.1801 -0.0884 0.074 Uiso 1 1 calc . . R C32 C 0.36805(16) 0.7360(3) 0.82688(13) 0.0559(9) Uani 1 1 d . . . H32 H 0.3879 0.7195 0.8598 0.067 Uiso 1 1 calc . . R C17 C 0.71309(14) 0.9548(3) 0.70626(14) 0.0545(9) Uani 1 1 d . . . C63 C 0.36301(19) 0.1942(3) 0.15019(14) 0.0698(11) Uani 1 1 d . . . H63 H 0.3297 0.1754 0.1248 0.084 Uiso 1 1 calc . . R C31 C 0.31590(15) 0.7832(2) 0.81355(13) 0.0481(8) Uani 1 1 d . . . C99 C 0.63281(16) 0.7105(3) 0.17265(13) 0.0580(9) Uani 1 1 d . . . H99 H 0.6614 0.6640 0.1871 0.070 Uiso 1 1 calc . . R C24 C 0.41830(16) 0.1294(2) 0.50548(12) 0.0497(9) Uani 1 1 d . . . C59 C 0.66796(16) 0.8535(3) 0.39954(13) 0.0562(9) Uani 1 1 d . . . H59 H 0.6602 0.8181 0.4241 0.067 Uiso 1 1 calc . . R C69B C 0.4969(3) 0.2926(5) 0.0418(3) 0.0468(15) Uani 0.769(11) 1 d A 3 . C19 C 0.65324(15) 0.8320(3) 0.72139(13) 0.0560(9) Uani 1 1 d . . . H19 H 0.6444 0.7897 0.7431 0.067 Uiso 1 1 calc . . R C36A C 0.5019(3) 0.7082(5) 0.2983(3) 0.0381(15) Uani 0.668(15) 1 d B 1 . C22 C 0.38248(14) 0.2937(2) 0.50336(12) 0.0450(8) Uani 1 1 d . . . H22 H 0.3542 0.3407 0.4891 0.054 Uiso 1 1 calc . . R C39 C 0.40722(14) 0.5843(2) 0.28970(11) 0.0444(8) Uani 1 1 d . . . C12 C 0.42560(17) 0.9384(3) 0.61795(15) 0.0668(11) Uani 1 1 d . . . H12A H 0.4334 1.0020 0.6340 0.100 Uiso 1 1 calc . . GR H12B H 0.3851 0.9266 0.6056 0.100 Uiso 1 1 calc . . GR H12C H 0.4395 0.9376 0.5909 0.100 Uiso 1 1 calc . . GR C9 C 0.33237(13) 0.5504(3) 0.60565(12) 0.0479(8) Uani 1 1 d . . . H9A H 0.3281 0.5581 0.6376 0.057 Uiso 1 1 calc . . R H9B H 0.3393 0.4806 0.6014 0.057 Uiso 1 1 calc . . R C97 C 0.59720(19) 0.8756(3) 0.16858(13) 0.0624(11) Uani 1 1 d . . . C71B C 0.5408(3) 0.4556(4) 0.0577(2) 0.0400(13) Uani 0.769(11) 1 d A 3 . C3 C 0.41657(13) 0.5781(2) 0.57723(11) 0.0389(7) Uani 1 1 d . . . C62 C 0.36846(16) 0.2886(3) 0.16869(13) 0.0580(9) Uani 1 1 d . . . H62 H 0.3389 0.3341 0.1557 0.070 Uiso 1 1 calc . . R C41 C 0.42284(18) 0.9246(3) 0.27608(15) 0.0730(11) Uani 1 1 d . . . H41A H 0.4410 0.9170 0.2520 0.109 Uiso 1 1 calc B . GR H41B H 0.4267 0.9922 0.2874 0.109 Uiso 1 1 calc . . GR H41C H 0.3830 0.9081 0.2613 0.109 Uiso 1 1 calc . . GR C13 C 0.53156(13) 0.7796(2) 0.60862(12) 0.0460(8) Uani 1 1 d . . . H13A H 0.5469 0.7561 0.5840 0.055 Uiso 1 1 calc . . R H13B H 0.5215 0.8492 0.6022 0.055 Uiso 1 1 calc . . R C82 C 0.63502(16) 0.2667(3) -0.15680(13) 0.0594(10) Uani 1 1 d . . . H82 H 0.6169 0.2804 -0.1903 0.071 Uiso 1 1 calc . . R C89 C 0.28852(17) 0.0796(3) -0.07790(15) 0.0679(11) Uani 1 1 d . . . H89 H 0.2665 0.0713 -0.1112 0.082 Uiso 1 1 calc . . R C23 C 0.37639(15) 0.1976(3) 0.48464(12) 0.0504(9) Uani 1 1 d . . . H23 H 0.3439 0.1800 0.4580 0.061 Uiso 1 1 calc . . R C58 C 0.71386(17) 0.9162(3) 0.41172(14) 0.0619(10) Uani 1 1 d . . . H58 H 0.7370 0.9241 0.4447 0.074 Uiso 1 1 calc . . R C18 C 0.69969(16) 0.8946(3) 0.73897(14) 0.0605(10) Uani 1 1 d . . . H18 H 0.7216 0.8960 0.7725 0.073 Uiso 1 1 calc . . R C45 C 0.30800(16) 0.5372(3) 0.23350(14) 0.0703(11) Uani 1 1 d . . . H45A H 0.3216 0.5212 0.2071 0.105 Uiso 1 1 calc B . GR H45B H 0.2968 0.6058 0.2311 0.105 Uiso 1 1 calc . . GR H45C H 0.2757 0.4962 0.2310 0.105 Uiso 1 1 calc . . GR C20 C 0.39882(13) 0.4869(2) 0.54525(12) 0.0454(8) Uani 1 1 d . . . H20A H 0.3612 0.4652 0.5439 0.055 Uiso 1 1 calc . . R H20B H 0.3970 0.5018 0.5118 0.055 Uiso 1 1 calc . . R C16 C 0.68029(17) 0.9562(3) 0.65724(14) 0.0655(11) Uani 1 1 d . . . H16 H 0.6893 0.9986 0.6356 0.079 Uiso 1 1 calc . . R C37A C 0.5050(3) 0.6065(5) 0.2885(3) 0.0358(15) Uani 0.668(15) 1 d B 1 . C51 C 0.35107(14) 0.7631(3) 0.48314(13) 0.0512(9) Uani 1 1 d . . . H51 H 0.3689 0.7551 0.5171 0.061 Uiso 1 1 calc . . R C53 C 0.54556(16) 0.7788(3) 0.29317(15) 0.0618(11) Uani 1 1 d . . . H53A H 0.5619 0.7548 0.2694 0.074 Uiso 0.668(15) 1 calc B 1 R H53B H 0.5293 0.8442 0.2832 0.074 Uiso 0.668(15) 1 calc B 1 R H53C H 0.5648 0.7551 0.2713 0.074 Uiso 0.332(15) 1 calc B 2 R H53D H 0.5347 0.8472 0.2840 0.074 Uiso 0.332(15) 1 calc B 2 R C4 C 0.38338(12) 0.6102(2) 0.60510(11) 0.0383(7) Uani 1 1 d . . . C70B C 0.4956(2) 0.3923(4) 0.0548(2) 0.0423(14) Uani 0.769(11) 1 d A 3 . C77 C 0.64182(16) 0.4847(3) 0.05358(13) 0.0566(9) Uani 1 1 d A . . H77A H 0.6305 0.5537 0.0530 0.068 Uiso 1 1 calc . . R H77B H 0.6549 0.4739 0.0261 0.068 Uiso 1 1 calc . . R C86 C 0.45291(17) 0.2216(3) 0.04391(15) 0.0616(10) Uani 1 1 d . . . H86A H 0.4688 0.1554 0.0519 0.074 Uiso 0.769(11) 1 calc A 3 R H86B H 0.4367 0.2418 0.0685 0.074 Uiso 0.769(11) 1 calc A 3 R H86C H 0.4630 0.1526 0.0519 0.074 Uiso 0.231(11) 1 calc A 4 R H86D H 0.4349 0.2448 0.0667 0.074 Uiso 0.231(11) 1 calc A 4 R C38A C 0.4583(3) 0.5434(5) 0.2850(3) 0.0377(15) Uani 0.668(15) 1 d B 1 . C78 C 0.69068(17) 0.4633(3) 0.10198(14) 0.0749(12) Uani 1 1 d . . . H78A H 0.7009 0.3944 0.1032 0.112 Uiso 1 1 calc A . GR H78B H 0.6787 0.4787 0.1293 0.112 Uiso 1 1 calc . . GR H78C H 0.7232 0.5035 0.1039 0.112 Uiso 1 1 calc . . GR C93 C 0.54006(16) 0.5630(3) 0.07160(14) 0.0602(10) Uani 1 1 d . . . H93A H 0.5486 0.6037 0.0473 0.072 Uiso 0.769(11) 1 calc A 3 R H93B H 0.5019 0.5802 0.0706 0.072 Uiso 0.769(11) 1 calc A 3 R H93C H 0.5467 0.6009 0.0456 0.072 Uiso 0.231(11) 1 calc A 4 R H93D H 0.5006 0.5701 0.0696 0.072 Uiso 0.231(11) 1 calc A 4 R C8 C 0.55797(15) 0.5433(3) 0.58694(14) 0.0618(10) Uani 1 1 d . . . H8A H 0.5802 0.5910 0.6106 0.093 Uiso 1 1 calc . . GR H8B H 0.5801 0.5181 0.5682 0.093 Uiso 1 1 calc . . GR H8C H 0.5476 0.4895 0.6039 0.093 Uiso 1 1 calc . . GR C2 C 0.46586(13) 0.6311(2) 0.57913(11) 0.0383(7) Uani 1 1 d . . . C75B C 0.4439(2) 0.4314(4) 0.06581(19) 0.0555(16) Uani 0.769(11) 1 d A 3 . H75A H 0.4336 0.4966 0.0511 0.067 Uiso 0.769(11) 1 calc A 3 R H75B H 0.4115 0.3875 0.0511 0.067 Uiso 0.769(11) 1 calc A 3 R C60 C 0.45972(16) 0.4367(3) 0.27128(14) 0.0590(9) Uani 1 1 d . . . H60A H 0.4981 0.4201 0.2727 0.071 Uiso 0.668(15) 1 calc B 1 R H60B H 0.4511 0.3957 0.2954 0.071 Uiso 0.668(15) 1 calc B 1 R H60C H 0.4989 0.4218 0.2747 0.071 Uiso 0.332(15) 1 calc B 2 R H60D H 0.4502 0.4037 0.2973 0.071 Uiso 0.332(15) 1 calc B 2 R C7 C 0.50384(13) 0.5929(3) 0.55199(12) 0.0468(8) Uani 1 1 d . . . H7A H 0.5145 0.6478 0.5353 0.056 Uiso 1 1 calc . . R H7B H 0.4825 0.5453 0.5270 0.056 Uiso 1 1 calc . . R C43A C 0.5549(4) 0.5505(6) 0.2312(3) 0.068(3) Uani 0.668(15) 1 d B 1 . H43A H 0.5442 0.6119 0.2135 0.102 Uiso 0.668(15) 1 calc B 1 GR H43B H 0.5262 0.5011 0.2163 0.102 Uiso 0.668(15) 1 calc B 1 GR H43C H 0.5910 0.5286 0.2302 0.102 Uiso 0.668(15) 1 calc B 1 GR C10 C 0.27669(14) 0.5821(3) 0.56490(13) 0.0647(10) Uani 1 1 d . . . H10A H 0.2696 0.6511 0.5689 0.097 Uiso 1 1 calc . . GR H10B H 0.2455 0.5432 0.5672 0.097 Uiso 1 1 calc . . GR H10C H 0.2801 0.5720 0.5331 0.097 Uiso 1 1 calc . . GR C76B C 0.4565(3) 0.4382(5) 0.1206(2) 0.078(2) Uani 0.769(11) 1 d A 3 . H76A H 0.4253 0.4704 0.1266 0.117 Uiso 0.769(11) 1 calc A 3 GR H76B H 0.4910 0.4758 0.1357 0.117 Uiso 0.769(11) 1 calc A 3 GR H76C H 0.4615 0.3726 0.1345 0.117 Uiso 0.769(11) 1 calc A 3 GR C42A C 0.5599(3) 0.5658(5) 0.2847(3) 0.050(2) Uani 0.668(15) 1 d B 1 . H42A H 0.5690 0.5030 0.3021 0.060 Uiso 0.668(15) 1 calc B 1 R H42B H 0.5909 0.6117 0.3004 0.060 Uiso 0.668(15) 1 calc B 1 R C75A C 0.4809(6) 0.4044(12) 0.1074(6) 0.041(5) Uiso 0.231(11) 1 d A 4 . H75C H 0.4999 0.4562 0.1307 0.050 Uiso 0.231(11) 1 calc A 4 R H75D H 0.4780 0.3467 0.1265 0.050 Uiso 0.231(11) 1 calc A 4 R C37B C 0.4860(8) 0.6210(12) 0.2652(8) 0.052(4) Uani 0.332(15) 1 d B 2 . C42B C 0.5295(6) 0.5859(10) 0.2429(6) 0.066(5) Uani 0.332(15) 1 d B 2 . H42C H 0.5368 0.6398 0.2236 0.079 Uiso 0.332(15) 1 calc B 2 R H42D H 0.5128 0.5316 0.2203 0.079 Uiso 0.332(15) 1 calc B 2 R C70A C 0.5184(9) 0.3777(13) 0.0785(8) 0.048(5) Uiso 0.231(11) 1 d A 4 . C76A C 0.4194(10) 0.4402(16) 0.0776(9) 0.075(7) Uiso 0.231(11) 1 d A 4 . H76D H 0.3993 0.3889 0.0550 0.112 Uiso 0.231(11) 1 calc A 4 GR H76E H 0.4213 0.4988 0.0592 0.112 Uiso 0.231(11) 1 calc A 4 GR H76F H 0.3997 0.4550 0.0999 0.112 Uiso 0.231(11) 1 calc A 4 GR C43B C 0.5878(10) 0.5505(14) 0.2810(10) 0.114(8) Uani 0.332(15) 1 d B 2 . H43D H 0.6112 0.5242 0.2637 0.171 Uiso 0.332(15) 1 calc B 2 GR H43E H 0.5811 0.4997 0.3017 0.171 Uiso 0.332(15) 1 calc B 2 GR H43F H 0.6070 0.6056 0.3011 0.171 Uiso 0.332(15) 1 calc B 2 GR C36B C 0.4885(5) 0.7175(9) 0.2807(5) 0.025(3) Uiso 0.332(15) 1 d B 2 . C38B C 0.4473(6) 0.5552(12) 0.2693(6) 0.037(4) Uiso 0.332(15) 1 d B 2 . C71A C 0.5602(10) 0.4455(18) 0.0730(9) 0.054(7) Uiso 0.231(11) 1 d A 4 . C69A C 0.5126(8) 0.2838(17) 0.0558(7) 0.030(5) Uiso 0.231(11) 1 d A 4 . 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 Cl4 0.2322(18) 0.0455(6) 0.0596(7) -0.0122(5) 0.0186(9) -0.0218(9) Cl2 0.1522(11) 0.0366(5) 0.0607(6) -0.0088(5) 0.0243(7) -0.0025(6) Cl7 0.2024(15) 0.0440(6) 0.0649(7) -0.0131(5) 0.0173(8) -0.0299(8) Cl9 0.0831(7) 0.0993(9) 0.0829(7) -0.0005(6) 0.0535(6) 0.0118(6) Cl3 0.0818(7) 0.0910(8) 0.0719(7) -0.0107(6) 0.0506(6) 0.0034(6) Cl5 0.0916(8) 0.0805(7) 0.0933(8) 0.0076(6) 0.0631(7) 0.0207(6) Cl1 0.0694(7) 0.0931(9) 0.1043(9) -0.0093(7) 0.0066(6) -0.0350(6) Cl6 0.0617(7) 0.1163(10) 0.0958(8) -0.0248(8) 0.0118(6) -0.0344(7) Cl8 0.0890(9) 0.1149(10) 0.1005(9) -0.0222(8) 0.0148(7) -0.0424(8) O3 0.0472(13) 0.0672(15) 0.0354(12) 0.0012(11) 0.0172(10) 0.0168(12) O9 0.0625(15) 0.0714(17) 0.0421(13) 0.0046(12) 0.0211(12) 0.0205(13) O5 0.0510(14) 0.0764(17) 0.0457(14) 0.0052(12) 0.0201(11) 0.0219(13) O1 0.0435(13) 0.0504(14) 0.0552(14) 0.0121(12) 0.0126(11) -0.0079(11) O8 0.0773(18) 0.0566(16) 0.0644(17) 0.0082(14) 0.0273(15) -0.0133(14) C28 0.0402(17) 0.0416(18) 0.0400(18) -0.0022(15) 0.0164(15) 0.0023(15) C80 0.0489(19) 0.0432(19) 0.0462(19) 0.0001(16) 0.0222(16) 0.0011(16) O4 0.0644(16) 0.0418(14) 0.0644(16) -0.0002(12) 0.0116(13) 0.0042(12) O2 0.0488(13) 0.0356(12) 0.0599(14) -0.0086(11) 0.0064(11) 0.0027(11) C47 0.0419(18) 0.0443(19) 0.0458(19) 0.0004(16) 0.0186(15) 0.0057(15) O6 0.0691(17) 0.0559(16) 0.0725(18) -0.0040(14) 0.0345(15) -0.0206(14) C46 0.0446(19) 0.051(2) 0.0401(18) 0.0026(16) 0.0095(15) 0.0036(16) O7 0.0762(17) 0.0392(14) 0.0604(16) -0.0049(12) 0.0210(14) -0.0030(13) C79 0.056(2) 0.054(2) 0.0397(19) -0.0025(16) 0.0154(16) 0.0033(17) C35 0.0513(19) 0.0351(18) 0.0407(18) -0.0038(15) 0.0159(15) 0.0021(15) C48 0.0439(18) 0.045(2) 0.0487(19) 0.0030(16) 0.0151(16) 0.0020(16) C27 0.0413(17) 0.0451(19) 0.0395(17) -0.0025(15) 0.0126(14) 0.0068(15) C67 0.060(2) 0.0370(19) 0.0403(18) -0.0018(15) 0.0207(17) -0.0014(16) C68 0.057(2) 0.0339(18) 0.0381(17) -0.0020(15) 0.0122(16) -0.0027(16) C14 0.0369(17) 0.0411(19) 0.050(2) 0.0048(16) 0.0157(16) -0.0017(15) C61 0.056(2) 0.0345(19) 0.053(2) 0.0025(16) 0.0194(18) -0.0057(16) C5 0.0395(17) 0.0349(17) 0.0343(16) 0.0004(14) 0.0113(14) 0.0023(14) C87 0.062(2) 0.042(2) 0.058(2) 0.0002(18) 0.029(2) -0.0030(18) C29 0.0457(19) 0.049(2) 0.0425(18) -0.0055(16) 0.0140(16) 0.0004(16) C34 0.0457(18) 0.0400(18) 0.0363(17) 0.0000(14) 0.0141(14) -0.0034(15) C6 0.0384(16) 0.0281(16) 0.0359(16) -0.0026(13) 0.0096(13) 0.0026(13) C66 0.058(2) 0.0359(19) 0.055(2) 0.0002(17) 0.0098(17) -0.0014(17) C85 0.048(2) 0.045(2) 0.051(2) 0.0037(17) 0.0147(17) 0.0025(16) C21 0.0420(17) 0.0302(17) 0.0409(17) -0.0071(14) 0.0151(15) -0.0049(14) C54 0.052(2) 0.0376(19) 0.058(2) -0.0006(17) 0.0261(18) -0.0045(16) C95 0.060(2) 0.041(2) 0.048(2) -0.0047(17) 0.0036(17) -0.0009(18) C40 0.052(2) 0.0405(19) 0.052(2) -0.0087(17) 0.0165(17) -0.0030(16) C49 0.0360(18) 0.045(2) 0.072(2) 0.0019(18) 0.0184(18) 0.0040(15) C91 0.095(3) 0.078(3) 0.062(3) -0.008(2) 0.034(2) -0.035(3) C94 0.060(2) 0.0370(19) 0.048(2) -0.0024(16) 0.0242(18) -0.0081(17) C81 0.057(2) 0.074(3) 0.047(2) 0.0074(19) 0.0185(18) 0.016(2) C11 0.0468(19) 0.0393(19) 0.052(2) -0.0107(16) 0.0161(16) -0.0012(15) C26 0.050(2) 0.042(2) 0.0447(19) 0.0003(16) 0.0022(16) 0.0049(16) C33 0.057(2) 0.065(2) 0.050(2) 0.0019(19) 0.0231(18) 0.0124(19) C96 0.093(3) 0.037(2) 0.053(2) -0.0036(18) 0.012(2) 0.005(2) C56 0.063(2) 0.063(2) 0.055(2) -0.0064(19) 0.0249(19) -0.020(2) C30 0.0454(19) 0.044(2) 0.065(2) -0.0073(18) 0.0256(18) 0.0024(16) C72 0.066(2) 0.0363(18) 0.0383(18) -0.0044(15) 0.0225(17) -0.0104(17) C90 0.066(2) 0.062(2) 0.057(2) -0.013(2) 0.013(2) -0.012(2) C25 0.076(3) 0.040(2) 0.052(2) -0.0001(17) 0.016(2) 0.0129(19) C52 0.0426(19) 0.066(2) 0.053(2) 0.0071(19) 0.0168(17) 0.0200(18) C73 0.067(2) 0.0350(19) 0.055(2) -0.0118(17) 0.0151(18) -0.0051(18) C74 0.096(3) 0.037(2) 0.081(3) 0.003(2) 0.006(2) 0.001(2) C44 0.050(2) 0.045(2) 0.064(2) 0.0083(18) 0.0232(18) -0.0059(17) C64 0.104(3) 0.041(2) 0.043(2) -0.0032(18) 0.017(2) -0.013(2) C98 0.068(3) 0.068(3) 0.049(2) -0.007(2) 0.010(2) -0.030(2) C92 0.092(3) 0.071(3) 0.046(2) -0.011(2) 0.027(2) -0.032(2) C65 0.088(3) 0.044(2) 0.055(2) -0.0031(19) 0.018(2) 0.004(2) C83 0.053(2) 0.046(2) 0.061(2) -0.0030(18) 0.0294(19) -0.0018(17) C57 0.044(2) 0.058(2) 0.064(2) -0.015(2) 0.0141(18) -0.0079(17) C55 0.061(2) 0.064(2) 0.0435(19) -0.0105(18) 0.0193(17) -0.0215(19) C50 0.054(2) 0.0387(19) 0.066(2) 0.0000(17) 0.032(2) -0.0064(16) C1 0.0370(16) 0.0363(17) 0.0408(17) 0.0056(15) 0.0133(14) 0.0013(14) C84 0.046(2) 0.046(2) 0.074(3) -0.0023(19) 0.027(2) 0.0013(16) C15 0.066(2) 0.060(2) 0.0443(19) -0.0014(18) 0.0195(18) -0.027(2) C88 0.069(3) 0.059(2) 0.060(2) 0.011(2) 0.027(2) 0.016(2) C32 0.066(2) 0.064(2) 0.045(2) -0.0005(18) 0.0285(18) 0.005(2) C17 0.044(2) 0.049(2) 0.065(2) -0.0053(19) 0.0120(18) -0.0081(17) C63 0.078(3) 0.074(3) 0.047(2) -0.004(2) 0.009(2) -0.025(2) C31 0.060(2) 0.046(2) 0.048(2) -0.0078(17) 0.0310(18) -0.0079(17) C99 0.057(2) 0.061(2) 0.052(2) -0.0037(19) 0.0138(18) -0.0039(19) C24 0.074(2) 0.0381(19) 0.0389(19) -0.0069(16) 0.0223(18) -0.0086(18) C59 0.066(2) 0.057(2) 0.050(2) 0.0116(19) 0.024(2) 0.010(2) C69B 0.052(4) 0.039(3) 0.044(4) -0.001(3) 0.011(3) -0.006(3) C19 0.047(2) 0.057(2) 0.059(2) 0.0187(19) 0.0127(18) -0.0005(18) C36A 0.042(3) 0.041(3) 0.023(3) 0.004(3) 0.002(3) -0.008(2) C22 0.0419(18) 0.043(2) 0.049(2) -0.0052(16) 0.0148(16) 0.0024(15) C39 0.0461(19) 0.043(2) 0.0438(19) 0.0027(16) 0.0160(16) -0.0078(16) C12 0.077(3) 0.036(2) 0.081(3) 0.000(2) 0.019(2) 0.0052(19) C9 0.0414(18) 0.050(2) 0.056(2) -0.0014(17) 0.0216(16) -0.0081(16) C97 0.099(3) 0.040(2) 0.044(2) -0.0059(18) 0.020(2) -0.019(2) C71B 0.048(3) 0.030(3) 0.038(3) -0.003(2) 0.010(3) -0.002(2) C3 0.0400(17) 0.0355(17) 0.0377(17) 0.0006(14) 0.0090(14) 0.0047(14) C62 0.052(2) 0.058(2) 0.057(2) 0.0063(19) 0.0103(18) -0.0022(19) C41 0.090(3) 0.041(2) 0.074(3) 0.004(2) 0.012(2) 0.003(2) C13 0.0464(19) 0.0435(19) 0.0474(19) 0.0037(16) 0.0155(16) -0.0083(15) C82 0.067(2) 0.068(3) 0.047(2) 0.0078(19) 0.0254(19) 0.007(2) C89 0.062(3) 0.077(3) 0.053(2) 0.002(2) 0.006(2) 0.010(2) C23 0.057(2) 0.046(2) 0.046(2) -0.0096(17) 0.0144(17) -0.0115(18) C58 0.065(3) 0.067(3) 0.046(2) -0.003(2) 0.0108(19) 0.012(2) C18 0.054(2) 0.063(2) 0.054(2) 0.006(2) 0.0056(18) 0.005(2) C45 0.057(2) 0.062(3) 0.076(3) -0.003(2) 0.004(2) -0.014(2) C20 0.0407(17) 0.0448(19) 0.0455(19) -0.0081(16) 0.0085(15) 0.0038(15) C16 0.075(3) 0.064(3) 0.062(2) -0.008(2) 0.030(2) -0.027(2) C37A 0.030(3) 0.036(3) 0.035(3) 0.004(3) 0.002(3) -0.005(2) C51 0.050(2) 0.057(2) 0.0448(19) 0.0031(17) 0.0138(17) 0.0084(18) C53 0.064(2) 0.052(2) 0.082(3) -0.018(2) 0.040(2) -0.0260(19) C4 0.0379(16) 0.0390(18) 0.0373(17) -0.0010(14) 0.0122(14) -0.0031(14) C70B 0.042(3) 0.041(3) 0.045(3) -0.003(2) 0.017(3) -0.007(2) C77 0.070(2) 0.045(2) 0.057(2) -0.0008(18) 0.0247(19) -0.0131(19) C86 0.079(3) 0.042(2) 0.076(3) -0.002(2) 0.042(2) -0.017(2) C38A 0.050(4) 0.031(3) 0.027(3) 0.007(3) 0.007(3) -0.004(2) C78 0.076(3) 0.071(3) 0.067(3) -0.001(2) 0.012(2) -0.018(2) C93 0.065(2) 0.041(2) 0.072(3) -0.0168(19) 0.021(2) -0.0071(18) C8 0.048(2) 0.071(3) 0.068(2) 0.001(2) 0.0220(19) 0.0098(19) C2 0.0377(16) 0.0394(18) 0.0375(17) 0.0023(14) 0.0128(14) 0.0043(14) C75B 0.058(3) 0.052(3) 0.059(3) 0.004(3) 0.024(3) 0.005(3) C60 0.058(2) 0.045(2) 0.071(3) -0.0093(19) 0.019(2) -0.0100(18) C7 0.0453(19) 0.055(2) 0.0437(18) -0.0016(16) 0.0202(16) 0.0052(16) C43A 0.068(5) 0.075(5) 0.070(5) -0.012(4) 0.035(4) -0.004(4) C10 0.043(2) 0.077(3) 0.066(2) -0.003(2) 0.0086(18) -0.0120(19) C76B 0.091(5) 0.089(4) 0.063(4) -0.005(3) 0.039(3) -0.005(4) C42A 0.045(4) 0.045(4) 0.053(4) 0.001(3) 0.008(3) 0.005(3) C37B 0.043(8) 0.056(8) 0.062(11) -0.001(8) 0.027(8) 0.014(7) C42B 0.064(9) 0.046(7) 0.109(13) -0.008(7) 0.057(10) 0.007(6) C43B 0.077(14) 0.076(11) 0.19(2) -0.004(12) 0.043(15) 0.038(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl4 C64 1.742(4) . ? Cl2 C24 1.752(3) . ? Cl7 C97 1.736(4) . ? Cl9 C83 1.750(3) . ? Cl3 C31 1.745(3) . ? Cl5 C50 1.749(3) . ? Cl1 C17 1.752(3) . ? Cl6 C57 1.744(4) . ? Cl8 C90 1.747(4) . ? O3 C28 1.378(3) . ? O3 C27 1.438(3) . ? O9 C80 1.370(3) . ? O9 C79 1.447(4) . ? O5 C47 1.370(3) . ? O5 C46 1.452(3) . ? O1 C14 1.381(4) . ? O1 C13 1.450(4) . ? O8 C87 1.374(4) . ? O8 C86 1.439(4) . ? C28 C29 1.382(4) . ? C28 C33 1.376(4) . ? C80 C85 1.380(4) . ? C80 C81 1.381(4) . ? O4 C61 1.382(4) . ? O4 C60 1.434(4) . ? O2 C21 1.374(3) . ? O2 C20 1.419(4) . ? C47 C48 1.383(4) . ? C47 C52 1.381(4) . ? O6 C54 1.367(4) . ? O6 C53 1.427(4) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C46 C34 1.514(4) . ? O7 C94 1.370(4) . ? O7 C93 1.433(4) . ? C79 H79A 0.9700 . ? C79 H79B 0.9700 . ? C79 C67 1.519(4) . ? C35 C34 1.383(4) . ? C35 C40 1.522(4) . ? C35 C36A 1.441(7) . ? C35 C36B 1.402(12) . ? C48 H48 0.9300 . ? C48 C49 1.392(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 C5 1.504(4) . ? C67 C68 1.380(4) . ? C67 C72 1.406(4) . ? C68 C73 1.525(4) . ? C68 C69B 1.451(7) . ? C68 C69A 1.35(2) . ? C14 C15 1.367(4) . ? C14 C19 1.378(4) . ? C61 C66 1.369(4) . ? C61 C62 1.387(5) . ? C5 C6 1.396(4) . ? C5 C4 1.402(4) . ? C87 C92 1.375(5) . ? C87 C88 1.387(5) . ? C29 H29 0.9300 . ? C29 C30 1.390(4) . ? C34 C39 1.404(4) . ? C6 C11 1.507(4) . ? C6 C1 1.406(4) . ? C66 H66 0.9300 . ? C66 C65 1.395(5) . ? C85 H85 0.9300 . ? C85 C84 1.400(4) . ? C21 C26 1.377(4) . ? C21 C22 1.377(4) . ? C54 C55 1.379(4) . ? C54 C59 1.385(5) . ? C95 H95 0.9300 . ? C95 C94 1.373(5) . ? C95 C96 1.389(5) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C40 C41 1.522(5) . ? C49 H49 0.9300 . ? C49 C50 1.376(5) . ? C91 H91 0.9300 . ? C91 C90 1.364(5) . ? C91 C92 1.380(5) . ? C94 C99 1.383(5) . ? C81 H81 0.9300 . ? C81 C82 1.377(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.526(5) . ? C26 H26 0.9300 . ? C26 C25 1.389(4) . ? C33 H33 0.9300 . ? C33 C32 1.367(4) . ? C96 H96 0.9300 . ? C96 C97 1.362(5) . ? C56 H56 0.9300 . ? C56 C57 1.373(5) . ? C56 C55 1.386(4) . ? C30 H30 0.9300 . ? C30 C31 1.361(5) . ? C72 C71B 1.464(7) . ? C72 C77 1.509(4) . ? C72 C71A 1.28(2) . ? C90 C89 1.368(5) . ? C25 H25 0.9300 . ? C25 C24 1.381(5) . ? C52 H52 0.9300 . ? C52 C51 1.373(4) . ? C73 H73A 0.9700 . ? C73 H73B 0.9700 . ? C73 C74 1.518(5) . ? C74 H74A 0.9600 . ? C74 H74B 0.9600 . ? C74 H74C 0.9600 . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C44 C39 1.517(4) . ? C44 C45 1.524(5) . ? C64 C65 1.369(5) . ? C64 C63 1.376(5) . ? C98 H98 0.9300 . ? C98 C99 1.376(5) . ? C98 C97 1.372(5) . ? C92 H92 0.9300 . ? C65 H65 0.9300 . ? C83 C84 1.358(5) . ? C83 C82 1.377(5) . ? C57 C58 1.367(5) . ? C55 H55 0.9300 . ? C50 C51 1.371(4) . ? C1 C13 1.505(4) . ? C1 C2 1.404(4) . ? C84 H84 0.9300 . ? C15 H15 0.9300 . ? C15 C16 1.389(5) . ? C88 H88 0.9300 . ? C88 C89 1.357(5) . ? C32 H32 0.9300 . ? C32 C31 1.376(5) . ? C17 C18 1.372(5) . ? C17 C16 1.363(5) . ? C63 H63 0.9300 . ? C63 C62 1.366(5) . ? C99 H99 0.9300 . ? C24 C23 1.362(5) . ? C59 H59 0.9300 . ? C59 C58 1.366(5) . ? C69B C70B 1.397(8) . ? C69B C86 1.473(7) . ? C19 H19 0.9300 . ? C19 C18 1.377(5) . ? C36A C37A 1.406(9) . ? C36A C53 1.493(6) . ? C22 H22 0.9300 . ? C22 C23 1.390(4) . ? C39 C38A 1.438(8) . ? C39 C38B 1.383(15) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C4 1.511(4) . ? C9 C10 1.532(5) . ? C71B C70B 1.391(7) . ? C71B C93 1.502(6) . ? C3 C20 1.506(4) . ? C3 C4 1.410(4) . ? C3 C2 1.406(4) . ? C62 H62 0.9300 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C82 H82 0.9300 . ? C89 H89 0.9300 . ? C23 H23 0.9300 . ? C58 H58 0.9300 . ? C18 H18 0.9300 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C16 H16 0.9300 . ? C37A C38A 1.417(9) . ? C37A C42A 1.513(11) . ? C51 H51 0.9300 . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C53 H53C 0.9700 . ? C53 H53D 0.9700 . ? C53 C36B 1.574(12) . ? C70B C75B 1.528(8) . ? C77 H77A 0.9700 . ? C77 H77B 0.9700 . ? C77 C78 1.524(5) . ? C86 H86A 0.9700 . ? C86 H86B 0.9700 . ? C86 H86C 0.9700 . ? C86 H86D 0.9700 . ? C86 C69A 1.64(2) . ? C38A C60 1.494(7) . ? C78 H78A 0.9600 . ? C78 H78B 0.9600 . ? C78 H78C 0.9600 . ? C93 H93A 0.9700 . ? C93 H93B 0.9700 . ? C93 H93C 0.9700 . ? C93 H93D 0.9700 . ? C93 C71A 1.66(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C8 C7 1.526(4) . ? C2 C7 1.516(4) . ? C75B H75A 0.9700 . ? C75B H75B 0.9700 . ? C75B C76B 1.503(8) . ? C60 H60A 0.9700 . ? C60 H60B 0.9700 . ? C60 H60C 0.9700 . ? C60 H60D 0.9700 . ? C60 C38B 1.623(16) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C43A H43A 0.9600 . ? C43A H43B 0.9600 . ? C43A H43C 0.9600 . ? C43A C42A 1.517(12) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C76B H76A 0.9600 . ? C76B H76B 0.9600 . ? C76B H76C 0.9600 . ? C42A H42A 0.9700 . ? C42A H42B 0.9700 . ? C75A H75C 0.9700 . ? C75A H75D 0.9700 . ? C75A C70A 1.50(2) . ? C75A C76A 1.55(3) . ? C37B C42B 1.52(2) . ? C37B C36B 1.368(18) . ? C37B C38B 1.35(2) . ? C42B H42C 0.9700 . ? C42B H42D 0.9700 . ? C42B C43B 1.56(3) . ? C70A C71A 1.44(3) . ? C70A C69A 1.41(3) . ? C76A H76D 0.9600 . ? C76A H76E 0.9600 . ? C76A H76F 0.9600 . ? C43B H43D 0.9600 . ? C43B H43E 0.9600 . ? C43B H43F 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 C28 O3 C27 117.4(2) . . ? C80 O9 C79 118.6(2) . . ? C47 O5 C46 119.1(2) . . ? C14 O1 C13 117.3(2) . . ? C87 O8 C86 116.5(3) . . ? O3 C28 C29 124.3(3) . . ? C33 C28 O3 116.3(3) . . ? C33 C28 C29 119.3(3) . . ? O9 C80 C85 124.5(3) . . ? O9 C80 C81 115.6(3) . . ? C85 C80 C81 119.8(3) . . ? C61 O4 C60 117.5(3) . . ? C21 O2 C20 118.0(2) . . ? O5 C47 C48 124.9(3) . . ? O5 C47 C52 115.3(3) . . ? C52 C47 C48 119.8(3) . . ? C54 O6 C53 117.3(3) . . ? O5 C46 H46A 111.0 . . ? O5 C46 H46B 111.0 . . ? O5 C46 C34 104.0(2) . . ? H46A C46 H46B 109.0 . . ? C34 C46 H46A 111.0 . . ? C34 C46 H46B 111.0 . . ? C94 O7 C93 116.2(3) . . ? O9 C79 H79A 110.8 . . ? O9 C79 H79B 110.8 . . ? O9 C79 C67 104.6(3) . . ? H79A C79 H79B 108.9 . . ? C67 C79 H79A 110.8 . . ? C67 C79 H79B 110.8 . . ? C34 C35 C40 121.1(3) . . ? C34 C35 C36A 120.1(3) . . ? C34 C35 C36B 118.1(5) . . ? C36A C35 C40 118.4(3) . . ? C36B C35 C40 118.8(5) . . ? C36B C35 C36A 20.9(4) . . ? C47 C48 H48 120.2 . . ? C47 C48 C49 119.6(3) . . ? C49 C48 H48 120.2 . . ? O3 C27 H27A 110.3 . . ? O3 C27 H27B 110.3 . . ? O3 C27 C5 107.1(2) . . ? H27A C27 H27B 108.6 . . ? C5 C27 H27A 110.3 . . ? C5 C27 H27B 110.3 . . ? C68 C67 C79 119.1(3) . . ? C68 C67 C72 121.6(3) . . ? C72 C67 C79 119.1(3) . . ? C67 C68 C73 121.9(3) . . ? C67 C68 C69B 120.3(4) . . ? C69B C68 C73 117.7(4) . . ? C69A C68 C67 116.2(10) . . ? C69A C68 C73 119.7(10) . . ? C69A C68 C69B 18.8(8) . . ? C15 C14 O1 124.1(3) . . ? C15 C14 C19 119.5(3) . . ? C19 C14 O1 116.4(3) . . ? O4 C61 C62 116.1(3) . . ? C66 C61 O4 123.7(3) . . ? C66 C61 C62 120.2(3) . . ? C6 C5 C27 119.2(3) . . ? C6 C5 C4 121.2(2) . . ? C4 C5 C27 119.6(3) . . ? O8 C87 C92 125.0(3) . . ? O8 C87 C88 116.0(3) . . ? C92 C87 C88 118.9(3) . . ? C28 C29 H29 120.4 . . ? C28 C29 C30 119.3(3) . . ? C30 C29 H29 120.4 . . ? C35 C34 C46 119.3(3) . . ? C35 C34 C39 120.8(3) . . ? C39 C34 C46 119.7(3) . . ? C5 C6 C11 120.6(2) . . ? C5 C6 C1 119.3(3) . . ? C1 C6 C11 119.9(3) . . ? C61 C66 H66 120.3 . . ? C61 C66 C65 119.4(3) . . ? C65 C66 H66 120.3 . . ? C80 C85 H85 120.6 . . ? C80 C85 C84 118.9(3) . . ? C84 C85 H85 120.6 . . ? O2 C21 C26 115.0(3) . . ? O2 C21 C22 125.1(3) . . ? C26 C21 C22 120.0(3) . . ? O6 C54 C55 124.8(3) . . ? O6 C54 C59 115.8(3) . . ? C55 C54 C59 119.4(3) . . ? C94 C95 H95 119.8 . . ? C94 C95 C96 120.5(3) . . ? C96 C95 H95 119.8 . . ? C35 C40 H40A 108.9 . . ? C35 C40 H40B 108.9 . . ? H40A C40 H40B 107.7 . . ? C41 C40 C35 113.4(3) . . ? C41 C40 H40A 108.9 . . ? C41 C40 H40B 108.9 . . ? C48 C49 H49 120.4 . . ? C50 C49 C48 119.2(3) . . ? C50 C49 H49 120.4 . . ? C90 C91 H91 120.4 . . ? C90 C91 C92 119.1(4) . . ? C92 C91 H91 120.4 . . ? O7 C94 C95 124.3(3) . . ? O7 C94 C99 116.5(3) . . ? C95 C94 C99 119.1(3) . . ? C80 C81 H81 119.4 . . ? C82 C81 C80 121.2(3) . . ? C82 C81 H81 119.4 . . ? C6 C11 H11A 109.4 . . ? C6 C11 H11B 109.4 . . ? C6 C11 C12 111.3(3) . . ? H11A C11 H11B 108.0 . . ? C12 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? C21 C26 H26 120.1 . . ? C21 C26 C25 119.9(3) . . ? C25 C26 H26 120.1 . . ? C28 C33 H33 119.4 . . ? C32 C33 C28 121.3(3) . . ? C32 C33 H33 119.4 . . ? C95 C96 H96 120.2 . . ? C97 C96 C95 119.7(4) . . ? C97 C96 H96 120.2 . . ? C57 C56 H56 120.5 . . ? C57 C56 C55 119.0(3) . . ? C55 C56 H56 120.5 . . ? C29 C30 H30 119.9 . . ? C31 C30 C29 120.3(3) . . ? C31 C30 H30 119.9 . . ? C67 C72 C71B 117.4(3) . . ? C67 C72 C77 121.0(3) . . ? C71B C72 C77 121.6(3) . . ? C71A C72 C67 120.4(11) . . ? C71A C72 C71B 21.6(10) . . ? C71A C72 C77 114.6(11) . . ? C91 C90 Cl8 118.4(3) . . ? C91 C90 C89 121.2(4) . . ? C89 C90 Cl8 120.4(3) . . ? C26 C25 H25 120.3 . . ? C24 C25 C26 119.5(3) . . ? C24 C25 H25 120.3 . . ? C47 C52 H52 119.6 . . ? C51 C52 C47 120.8(3) . . ? C51 C52 H52 119.6 . . ? C68 C73 H73A 108.9 . . ? C68 C73 H73B 108.9 . . ? H73A C73 H73B 107.7 . . ? C74 C73 C68 113.6(3) . . ? C74 C73 H73A 108.9 . . ? C74 C73 H73B 108.9 . . ? C73 C74 H74A 109.5 . . ? C73 C74 H74B 109.5 . . ? C73 C74 H74C 109.5 . . ? H74A C74 H74B 109.5 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? H44A C44 H44B 107.9 . . ? C39 C44 H44A 109.3 . . ? C39 C44 H44B 109.3 . . ? C39 C44 C45 111.8(3) . . ? C45 C44 H44A 109.3 . . ? C45 C44 H44B 109.3 . . ? C65 C64 Cl4 119.9(3) . . ? C65 C64 C63 120.6(3) . . ? C63 C64 Cl4 119.5(3) . . ? C99 C98 H98 120.0 . . ? C97 C98 H98 120.0 . . ? C97 C98 C99 120.1(4) . . ? C87 C92 C91 120.4(4) . . ? C87 C92 H92 119.8 . . ? C91 C92 H92 119.8 . . ? C66 C65 H65 120.1 . . ? C64 C65 C66 119.8(4) . . ? C64 C65 H65 120.1 . . ? C84 C83 Cl9 119.3(3) . . ? C84 C83 C82 121.7(3) . . ? C82 C83 Cl9 119.0(3) . . ? C56 C57 Cl6 118.6(3) . . ? C58 C57 Cl6 120.6(3) . . ? C58 C57 C56 120.7(3) . . ? C54 C55 C56 120.4(3) . . ? C54 C55 H55 119.8 . . ? C56 C55 H55 119.8 . . ? C49 C50 Cl5 119.9(3) . . ? C51 C50 Cl5 118.7(3) . . ? C51 C50 C49 121.4(3) . . ? C6 C1 C13 118.3(3) . . ? C2 C1 C6 120.4(3) . . ? C2 C1 C13 121.3(3) . . ? C85 C84 H84 120.0 . . ? C83 C84 C85 120.1(3) . . ? C83 C84 H84 120.0 . . ? C14 C15 H15 119.8 . . ? C14 C15 C16 120.4(3) . . ? C16 C15 H15 119.8 . . ? C87 C88 H88 119.7 . . ? C89 C88 C87 120.7(4) . . ? C89 C88 H88 119.7 . . ? C33 C32 H32 120.4 . . ? C33 C32 C31 119.2(3) . . ? C31 C32 H32 120.4 . . ? C18 C17 Cl1 119.3(3) . . ? C16 C17 Cl1 119.4(3) . . ? C16 C17 C18 121.3(3) . . ? C64 C63 H63 120.1 . . ? C62 C63 C64 119.9(4) . . ? C62 C63 H63 120.1 . . ? C30 C31 Cl3 119.1(3) . . ? C30 C31 C32 120.6(3) . . ? C32 C31 Cl3 120.3(3) . . ? C94 C99 H99 119.9 . . ? C98 C99 C94 120.2(4) . . ? C98 C99 H99 119.9 . . ? C25 C24 Cl2 119.2(3) . . ? C23 C24 Cl2 120.0(3) . . ? C23 C24 C25 120.8(3) . . ? C54 C59 H59 120.1 . . ? C58 C59 C54 119.9(3) . . ? C58 C59 H59 120.1 . . ? C68 C69B C86 119.4(5) . . ? C70B C69B C68 118.9(5) . . ? C70B C69B C86 121.6(5) . . ? C14 C19 H19 119.7 . . ? C18 C19 C14 120.6(3) . . ? C18 C19 H19 119.7 . . ? C35 C36A C53 119.0(5) . . ? C37A C36A C35 119.8(5) . . ? C37A C36A C53 120.4(5) . . ? C21 C22 H22 119.9 . . ? C21 C22 C23 120.2(3) . . ? C23 C22 H22 119.9 . . ? C34 C39 C44 120.1(3) . . ? C34 C39 C38A 119.3(4) . . ? C38A C39 C44 120.6(4) . . ? C38B C39 C34 117.8(7) . . ? C38B C39 C44 119.5(7) . . ? C38B C39 C38A 18.9(6) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H9A C9 H9B 107.8 . . ? C4 C9 H9A 109.1 . . ? C4 C9 H9B 109.1 . . ? C4 C9 C10 112.5(3) . . ? C10 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C96 C97 Cl7 119.9(3) . . ? C96 C97 C98 120.4(3) . . ? C98 C97 Cl7 119.7(3) . . ? C72 C71B C93 117.8(4) . . ? C70B C71B C72 120.7(4) . . ? C70B C71B C93 121.4(5) . . ? C4 C3 C20 119.6(3) . . ? C2 C3 C20 120.1(3) . . ? C2 C3 C4 120.2(3) . . ? C61 C62 H62 120.0 . . ? C63 C62 C61 120.1(4) . . ? C63 C62 H62 120.0 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41B 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O1 C13 C1 107.5(2) . . ? O1 C13 H13A 110.2 . . ? O1 C13 H13B 110.2 . . ? C1 C13 H13A 110.2 . . ? C1 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? C81 C82 C83 118.3(3) . . ? C81 C82 H82 120.9 . . ? C83 C82 H82 120.9 . . ? C90 C89 H89 120.2 . . ? C88 C89 C90 119.6(4) . . ? C88 C89 H89 120.2 . . ? C24 C23 C22 119.6(3) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C57 C58 H58 119.7 . . ? C59 C58 C57 120.5(3) . . ? C59 C58 H58 119.7 . . ? C17 C18 C19 119.0(3) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45B 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O2 C20 C3 108.6(2) . . ? O2 C20 H20A 110.0 . . ? O2 C20 H20B 110.0 . . ? C3 C20 H20A 110.0 . . ? C3 C20 H20B 110.0 . . ? H20A C20 H20B 108.3 . . ? C15 C16 H16 120.4 . . ? C17 C16 C15 119.1(3) . . ? C17 C16 H16 120.4 . . ? C36A C37A C38A 119.6(6) . . ? C36A C37A C42A 118.9(6) . . ? C38A C37A C42A 121.4(6) . . ? C52 C51 H51 120.4 . . ? C50 C51 C52 119.2(3) . . ? C50 C51 H51 120.4 . . ? O6 C53 C36A 102.4(4) . . ? O6 C53 H53A 111.3 . . ? O6 C53 H53B 111.3 . . ? O6 C53 H53C 107.0 . . ? O6 C53 H53D 107.0 . . ? O6 C53 C36B 121.4(6) . . ? C36A C53 H53A 111.3 . . ? C36A C53 H53B 111.3 . . ? C36A C53 H53C 113.6 . . ? C36A C53 H53D 119.3 . . ? C36A C53 C36B 19.2(4) . . ? H53A C53 H53B 109.2 . . ? H53A C53 H53C 4.4 . . ? H53A C53 H53D 105.5 . . ? H53B C53 H53C 110.9 . . ? H53B C53 H53D 8.0 . . ? H53C C53 H53D 106.7 . . ? C36B C53 H53A 103.6 . . ? C36B C53 H53B 99.0 . . ? C36B C53 H53C 107.0 . . ? C36B C53 H53D 107.0 . . ? C5 C4 C9 120.4(3) . . ? C5 C4 C3 119.0(3) . . ? C3 C4 C9 120.6(3) . . ? C69B C70B C75B 119.3(5) . . ? C71B C70B C69B 120.6(5) . . ? C71B C70B C75B 120.1(4) . . ? C72 C77 H77A 109.3 . . ? C72 C77 H77B 109.3 . . ? C72 C77 C78 111.7(3) . . ? H77A C77 H77B 107.9 . . ? C78 C77 H77A 109.3 . . ? C78 C77 H77B 109.3 . . ? O8 C86 C69B 104.3(4) . . ? O8 C86 H86A 110.9 . . ? O8 C86 H86B 110.9 . . ? O8 C86 H86C 107.4 . . ? O8 C86 H86D 107.4 . . ? O8 C86 C69A 119.8(7) . . ? C69B C86 H86A 110.9 . . ? C69B C86 H86B 110.9 . . ? C69B C86 H86C 119.7 . . ? C69B C86 H86D 110.5 . . ? C69B C86 C69A 16.3(7) . . ? H86A C86 H86B 108.9 . . ? H86A C86 H86C 8.8 . . ? H86A C86 H86D 112.5 . . ? H86B C86 H86C 103.6 . . ? H86B C86 H86D 4.0 . . ? H86C C86 H86D 106.9 . . ? C69A C86 H86A 98.8 . . ? C69A C86 H86B 106.6 . . ? C69A C86 H86C 107.4 . . ? C69A C86 H86D 107.4 . . ? C39 C38A C60 119.9(5) . . ? C37A C38A C39 119.9(5) . . ? C37A C38A C60 119.9(6) . . ? C77 C78 H78A 109.5 . . ? C77 C78 H78B 109.5 . . ? C77 C78 H78C 109.5 . . ? H78A C78 H78B 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? O7 C93 C71B 112.8(4) . . ? O7 C93 H93A 109.0 . . ? O7 C93 H93B 109.0 . . ? O7 C93 H93C 112.9 . . ? O7 C93 H93D 112.9 . . ? O7 C93 C71A 94.0(8) . . ? C71B C93 H93A 109.0 . . ? C71B C93 H93B 109.0 . . ? C71B C93 H93C 106.3 . . ? C71B C93 H93D 100.7 . . ? C71B C93 C71A 19.1(7) . . ? H93A C93 H93B 107.8 . . ? H93A C93 H93C 4.0 . . ? H93A C93 H93D 112.1 . . ? H93B C93 H93C 106.5 . . ? H93B C93 H93D 8.3 . . ? H93C C93 H93D 110.3 . . ? C71A C93 H93A 114.6 . . ? C71A C93 H93B 121.1 . . ? C71A C93 H93C 112.9 . . ? C71A C93 H93D 112.9 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? C1 C2 C3 119.6(3) . . ? C1 C2 C7 120.1(3) . . ? C3 C2 C7 120.3(3) . . ? C70B C75B H75A 109.4 . . ? C70B C75B H75B 109.4 . . ? H75A C75B H75B 108.0 . . ? C76B C75B C70B 111.1(6) . . ? C76B C75B H75A 109.4 . . ? C76B C75B H75B 109.4 . . ? O4 C60 C38A 113.1(4) . . ? O4 C60 H60A 109.0 . . ? O4 C60 H60B 109.0 . . ? O4 C60 H60C 112.4 . . ? O4 C60 H60D 112.4 . . ? O4 C60 C38B 96.8(6) . . ? C38A C60 H60A 109.0 . . ? C38A C60 H60B 109.0 . . ? C38A C60 H60C 106.8 . . ? C38A C60 H60D 101.5 . . ? C38A C60 C38B 16.6(5) . . ? H60A C60 H60B 107.8 . . ? H60A C60 H60C 3.4 . . ? H60A C60 H60D 111.7 . . ? H60B C60 H60C 106.3 . . ? H60B C60 H60D 7.5 . . ? H60C C60 H60D 109.9 . . ? C38B C60 H60A 113.6 . . ? C38B C60 H60B 119.8 . . ? C38B C60 H60C 112.4 . . ? C38B C60 H60D 112.4 . . ? C8 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C2 C7 C8 112.1(3) . . ? C2 C7 H7A 109.2 . . ? C2 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C37A C42A C43A 111.8(8) . . ? C37A C42A H42A 109.3 . . ? C37A C42A H42B 109.3 . . ? C43A C42A H42A 109.3 . . ? C43A C42A H42B 109.3 . . ? H42A C42A H42B 107.9 . . ? H75C C75A H75D 107.3 . . ? C70A C75A H75C 108.0 . . ? C70A C75A H75D 108.0 . . ? C70A C75A C76A 117(2) . . ? C76A C75A H75C 108.0 . . ? C76A C75A H75D 108.0 . . ? C36B C37B C42B 118.5(12) . . ? C38B C37B C42B 118.3(13) . . ? C38B C37B C36B 123.1(12) . . ? C37B C42B H42C 108.5 . . ? C37B C42B H42D 108.5 . . ? C37B C42B C43B 115(2) . . ? H42C C42B H42D 107.5 . . ? C43B C42B H42C 108.5 . . ? C43B C42B H42D 108.5 . . ? C71A C70A C75A 121.9(16) . . ? C69A C70A C75A 119.4(16) . . ? C69A C70A C71A 118.7(17) . . ? C42B C43B H43D 109.5 . . ? C42B C43B H43E 109.5 . . ? C42B C43B H43F 109.5 . . ? H43D C43B H43E 109.5 . . ? H43D C43B H43F 109.5 . . ? H43E C43B H43F 109.5 . . ? C35 C36B C53 116.1(8) . . ? C37B C36B C35 118.3(10) . . ? C37B C36B C53 120.4(10) . . ? C39 C38B C60 115.0(10) . . ? C37B C38B C39 120.0(12) . . ? C37B C38B C60 121.0(11) . . ? C72 C71A C93 119.1(16) . . ? C72 C71A C70A 119.2(19) . . ? C70A C71A C93 112.6(15) . . ? C68 C69A C86 115.1(15) . . ? C68 C69A C70A 121.4(18) . . ? C70A C69A C86 119.6(15) . . ? 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 Cl4 C64 C65 C66 -177.9(3) . . . . ? Cl4 C64 C63 C62 178.5(3) . . . . ? Cl2 C24 C23 C22 177.4(2) . . . . ? Cl9 C83 C84 C85 -179.9(2) . . . . ? Cl9 C83 C82 C81 179.3(3) . . . . ? Cl5 C50 C51 C52 179.9(3) . . . . ? Cl1 C17 C18 C19 -178.9(3) . . . . ? Cl1 C17 C16 C15 179.4(3) . . . . ? Cl6 C57 C58 C59 179.0(3) . . . . ? Cl8 C90 C89 C88 -179.8(3) . . . . ? O3 C28 C29 C30 -179.8(3) . . . . ? O3 C28 C33 C32 -179.6(3) . . . . ? O3 C27 C5 C6 -82.8(3) . . . . ? O3 C27 C5 C4 96.4(3) . . . . ? O9 C80 C85 C84 179.9(3) . . . . ? O9 C80 C81 C82 179.6(3) . . . . ? O9 C79 C67 C68 83.7(3) . . . . ? O9 C79 C67 C72 -91.0(4) . . . . ? O5 C47 C48 C49 -179.6(3) . . . . ? O5 C47 C52 C51 179.6(3) . . . . ? O5 C46 C34 C35 -84.8(3) . . . . ? O5 C46 C34 C39 89.6(3) . . . . ? O1 C14 C15 C16 179.5(3) . . . . ? O1 C14 C19 C18 -179.0(3) . . . . ? O8 C87 C92 C91 -179.7(4) . . . . ? O8 C87 C88 C89 179.8(3) . . . . ? O8 C86 C69A C68 -60.1(16) . . . . ? O8 C86 C69A C70A 98.2(16) . . . . ? C28 O3 C27 C5 -179.8(2) . . . . ? C28 C29 C30 C31 0.4(5) . . . . ? C28 C33 C32 C31 -1.5(6) . . . . ? C80 O9 C79 C67 -174.6(3) . . . . ? C80 C85 C84 C83 -0.1(5) . . . . ? C80 C81 C82 C83 1.2(6) . . . . ? O4 C61 C66 C65 -178.8(3) . . . . ? O4 C61 C62 C63 179.4(3) . . . . ? O4 C60 C38B C39 94.5(10) . . . . ? O4 C60 C38B C37B -108.2(12) . . . . ? O2 C21 C26 C25 177.6(3) . . . . ? O2 C21 C22 C23 -177.0(3) . . . . ? C47 O5 C46 C34 174.3(3) . . . . ? C47 C48 C49 C50 0.3(5) . . . . ? C47 C52 C51 C50 -0.2(5) . . . . ? O6 C54 C55 C56 178.1(3) . . . . ? O6 C54 C59 C58 -178.2(3) . . . . ? O6 C53 C36B C35 63.4(10) . . . . ? O6 C53 C36B C37B -90.6(11) . . . . ? C46 O5 C47 C48 4.2(5) . . . . ? C46 O5 C47 C52 -175.5(3) . . . . ? C46 C34 C39 C44 11.5(4) . . . . ? C46 C34 C39 C38A -165.5(4) . . . . ? C46 C34 C39 C38B 173.0(8) . . . . ? O7 C94 C99 C98 179.8(3) . . . . ? O7 C93 C71A C72 -105.1(16) . . . . ? O7 C93 C71A C70A 108.2(14) . . . . ? C79 O9 C80 C85 -2.1(5) . . . . ? C79 O9 C80 C81 177.9(3) . . . . ? C79 C67 C68 C73 4.5(5) . . . . ? C79 C67 C68 C69B -171.5(4) . . . . ? C79 C67 C68 C69A 167.6(9) . . . . ? C79 C67 C72 C71B 168.0(4) . . . . ? C79 C67 C72 C77 -11.0(5) . . . . ? C79 C67 C72 C71A -167.5(12) . . . . ? C35 C34 C39 C44 -174.2(3) . . . . ? C35 C34 C39 C38A 8.8(6) . . . . ? C35 C34 C39 C38B -12.7(9) . . . . ? C35 C36A C37A C38A 0.0(9) . . . . ? C35 C36A C37A C42A -176.7(6) . . . . ? C35 C36A C53 O6 98.8(6) . . . . ? C35 C36A C53 C36B -72.8(18) . . . . ? C48 C47 C52 C51 -0.2(5) . . . . ? C48 C49 C50 Cl5 -179.9(2) . . . . ? C48 C49 C50 C51 -0.7(5) . . . . ? C27 O3 C28 C29 4.7(4) . . . . ? C27 O3 C28 C33 -174.8(3) . . . . ? C27 C5 C6 C11 -6.4(4) . . . . ? C27 C5 C6 C1 178.7(3) . . . . ? C27 C5 C4 C9 -0.3(4) . . . . ? C27 C5 C4 C3 177.1(3) . . . . ? C67 C68 C73 C74 89.6(4) . . . . ? C67 C68 C69B C70B 2.2(8) . . . . ? C67 C68 C69B C86 -174.5(4) . . . . ? C67 C68 C69A C86 167.4(8) . . . . ? C67 C68 C69A C70A 9.5(19) . . . . ? C67 C72 C71B C70B 5.1(7) . . . . ? C67 C72 C71B C93 -174.9(4) . . . . ? C67 C72 C77 C78 -80.5(4) . . . . ? C67 C72 C71A C93 -153.1(10) . . . . ? C67 C72 C71A C70A -9(2) . . . . ? C68 C67 C72 C71B -6.6(5) . . . . ? C68 C67 C72 C77 174.4(3) . . . . ? C68 C67 C72 C71A 17.9(13) . . . . ? C68 C69B C70B C71B -3.7(9) . . . . ? C68 C69B C70B C75B 176.5(5) . . . . ? C68 C69B C86 O8 -91.4(6) . . . . ? C68 C69B C86 C69A 72(3) . . . . ? C14 O1 C13 C1 -166.7(2) . . . . ? C14 C15 C16 C17 0.7(6) . . . . ? C14 C19 C18 C17 -1.6(5) . . . . ? C61 O4 C60 C38A -179.9(4) . . . . ? C61 O4 C60 C38B 176.7(6) . . . . ? C61 C66 C65 C64 -0.7(5) . . . . ? C5 C6 C11 C12 -88.8(3) . . . . ? C5 C6 C1 C13 -178.2(3) . . . . ? C5 C6 C1 C2 2.3(4) . . . . ? C87 O8 C86 C69B 174.3(4) . . . . ? C87 O8 C86 C69A 168.9(9) . . . . ? C87 C88 C89 C90 -0.1(6) . . . . ? C29 C28 C33 C32 0.8(5) . . . . ? C29 C30 C31 Cl3 178.8(2) . . . . ? C29 C30 C31 C32 -1.1(5) . . . . ? C34 C35 C40 C41 -90.1(4) . . . . ? C34 C35 C36A C37A 2.1(7) . . . . ? C34 C35 C36A C53 171.1(4) . . . . ? C34 C35 C36B C53 -167.3(6) . . . . ? C34 C35 C36B C37B -12.7(12) . . . . ? C34 C39 C38A C37A -6.6(8) . . . . ? C34 C39 C38A C60 179.6(4) . . . . ? C34 C39 C38B C60 161.2(6) . . . . ? C34 C39 C38B C37B 3.7(14) . . . . ? C6 C5 C4 C9 178.8(3) . . . . ? C6 C5 C4 C3 -3.8(4) . . . . ? C6 C1 C13 O1 73.2(3) . . . . ? C6 C1 C2 C3 0.2(4) . . . . ? C6 C1 C2 C7 179.9(3) . . . . ? C66 C61 C62 C63 0.1(5) . . . . ? C85 C80 C81 C82 -0.5(6) . . . . ? C21 O2 C20 C3 177.9(2) . . . . ? C21 C26 C25 C24 -0.4(5) . . . . ? C21 C22 C23 C24 -0.6(5) . . . . ? C54 O6 C53 C36A -177.5(3) . . . . ? C54 O6 C53 C36B -174.3(5) . . . . ? C54 C59 C58 C57 -0.9(5) . . . . ? C95 C94 C99 C98 -0.7(5) . . . . ? C95 C96 C97 Cl7 178.0(3) . . . . ? C95 C96 C97 C98 0.2(6) . . . . ? C40 C35 C34 C46 -4.9(4) . . . . ? C40 C35 C34 C39 -179.2(3) . . . . ? C40 C35 C36A C37A 174.9(4) . . . . ? C40 C35 C36A C53 -16.0(8) . . . . ? C40 C35 C36B C53 28.8(12) . . . . ? C40 C35 C36B C37B -176.7(9) . . . . ? C49 C50 C51 C52 0.7(5) . . . . ? C91 C90 C89 C88 -0.7(6) . . . . ? C94 O7 C93 C71B 177.8(3) . . . . ? C94 O7 C93 C71A 174.2(8) . . . . ? C94 C95 C96 C97 0.0(6) . . . . ? C81 C80 C85 C84 -0.1(5) . . . . ? C11 C6 C1 C13 6.9(4) . . . . ? C11 C6 C1 C2 -172.7(3) . . . . ? C26 C21 C22 C23 2.4(5) . . . . ? C26 C25 C24 Cl2 -176.9(2) . . . . ? C26 C25 C24 C23 2.3(5) . . . . ? C33 C28 C29 C30 -0.3(5) . . . . ? C33 C32 C31 Cl3 -178.2(3) . . . . ? C33 C32 C31 C30 1.6(5) . . . . ? C96 C95 C94 O7 179.7(3) . . . . ? C96 C95 C94 C99 0.3(5) . . . . ? C56 C57 C58 C59 1.9(6) . . . . ? C72 C67 C68 C73 179.2(3) . . . . ? C72 C67 C68 C69B 3.2(6) . . . . ? C72 C67 C68 C69A -17.7(10) . . . . ? C72 C71B C70B C69B 0.0(8) . . . . ? C72 C71B C70B C75B 179.9(5) . . . . ? C72 C71B C93 O7 -70.6(5) . . . . ? C72 C71B C93 C71A -60(3) . . . . ? C90 C91 C92 C87 0.1(6) . . . . ? C25 C24 C23 C22 -1.8(5) . . . . ? C52 C47 C48 C49 0.2(5) . . . . ? C73 C68 C69B C70B -174.0(4) . . . . ? C73 C68 C69B C86 9.4(8) . . . . ? C73 C68 C69A C86 -29.1(16) . . . . ? C73 C68 C69A C70A 173.0(13) . . . . ? C44 C39 C38A C37A 176.5(4) . . . . ? C44 C39 C38A C60 2.7(8) . . . . ? C44 C39 C38B C60 -37.1(12) . . . . ? C44 C39 C38B C37B 165.3(10) . . . . ? C64 C63 C62 C61 -0.4(6) . . . . ? C92 C87 C88 C89 0.9(6) . . . . ? C92 C91 C90 Cl8 179.9(3) . . . . ? C92 C91 C90 C89 0.7(7) . . . . ? C65 C64 C63 C62 0.2(6) . . . . ? C57 C56 C55 C54 0.7(5) . . . . ? C55 C54 C59 C58 -0.2(5) . . . . ? C55 C56 C57 Cl6 -179.0(3) . . . . ? C55 C56 C57 C58 -1.8(6) . . . . ? C1 C6 C11 C12 86.0(4) . . . . ? C1 C2 C7 C8 77.8(4) . . . . ? C84 C83 C82 C81 -1.3(6) . . . . ? C15 C14 C19 C18 0.6(5) . . . . ? C88 C87 C92 C91 -0.9(6) . . . . ? C63 C64 C65 C66 0.4(6) . . . . ? C99 C98 C97 Cl7 -178.5(3) . . . . ? C99 C98 C97 C96 -0.7(6) . . . . ? C59 C54 C55 C56 0.2(5) . . . . ? C69B C68 C73 C74 -94.3(5) . . . . ? C69B C68 C69A C86 60(3) . . . . ? C69B C68 C69A C70A -98(4) . . . . ? C69B C70B C75B C76B 100.5(6) . . . . ? C69B C86 C69A C68 -79(3) . . . . ? C69B C86 C69A C70A 79(4) . . . . ? C19 C14 C15 C16 -0.1(5) . . . . ? C36A C35 C34 C46 167.7(4) . . . . ? C36A C35 C34 C39 -6.6(6) . . . . ? C36A C35 C40 C41 97.2(5) . . . . ? C36A C35 C36B C53 -65.8(17) . . . . ? C36A C35 C36B C37B 89(2) . . . . ? C36A C37A C38A C39 2.3(9) . . . . ? C36A C37A C38A C60 176.0(5) . . . . ? C36A C37A C42A C43A -102.0(6) . . . . ? C36A C53 C36B C35 73.0(18) . . . . ? C36A C53 C36B C37B -80.9(19) . . . . ? C22 C21 C26 C25 -1.9(5) . . . . ? C39 C38A C60 O4 63.8(7) . . . . ? C39 C38A C60 C38B 76(3) . . . . ? C97 C98 C99 C94 0.9(6) . . . . ? C71B C72 C77 C78 100.6(5) . . . . ? C71B C72 C71A C93 -65(3) . . . . ? C71B C72 C71A C70A 79(3) . . . . ? C71B C70B C75B C76B -79.4(6) . . . . ? C71B C93 C71A C72 85(3) . . . . ? C71B C93 C71A C70A -62(2) . . . . ? C3 C2 C7 C8 -102.5(3) . . . . ? C62 C61 C66 C65 0.5(5) . . . . ? C13 O1 C14 C15 -11.7(4) . . . . ? C13 O1 C14 C19 167.9(3) . . . . ? C13 C1 C2 C3 -179.3(3) . . . . ? C13 C1 C2 C7 0.4(4) . . . . ? C82 C83 C84 C85 0.8(5) . . . . ? C18 C17 C16 C15 -1.7(6) . . . . ? C45 C44 C39 C34 78.1(4) . . . . ? C45 C44 C39 C38A -105.0(5) . . . . ? C45 C44 C39 C38B -83.1(8) . . . . ? C20 O2 C21 C26 176.2(3) . . . . ? C20 O2 C21 C22 -4.4(4) . . . . ? C20 C3 C4 C5 -173.5(3) . . . . ? C20 C3 C4 C9 3.9(4) . . . . ? C20 C3 C2 C1 175.3(3) . . . . ? C20 C3 C2 C7 -4.4(4) . . . . ? C16 C17 C18 C19 2.2(6) . . . . ? C37A C36A C53 O6 -92.2(6) . . . . ? C37A C36A C53 C36B 96.2(18) . . . . ? C37A C38A C60 O4 -110.0(6) . . . . ? C37A C38A C60 C38B -98(3) . . . . ? C53 O6 C54 C55 -7.2(5) . . . . ? C53 O6 C54 C59 170.8(3) . . . . ? C53 C36A C37A C38A -168.9(6) . . . . ? C53 C36A C37A C42A 14.4(8) . . . . ? C4 C5 C6 C11 174.5(3) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? C4 C3 C20 O2 -111.7(3) . . . . ? C4 C3 C2 C1 -4.5(4) . . . . ? C4 C3 C2 C7 175.8(3) . . . . ? C70B C69B C86 O8 92.1(6) . . . . ? C70B C69B C86 C69A -105(4) . . . . ? C70B C71B C93 O7 109.5(5) . . . . ? C70B C71B C93 C71A 120(3) . . . . ? C77 C72 C71B C70B -176.0(4) . . . . ? C77 C72 C71B C93 4.1(7) . . . . ? C77 C72 C71A C93 49.0(19) . . . . ? C77 C72 C71A C70A -166.5(13) . . . . ? C86 O8 C87 C92 13.3(5) . . . . ? C86 O8 C87 C88 -165.4(3) . . . . ? C86 C69B C70B C71B 172.9(5) . . . . ? C86 C69B C70B C75B -6.9(8) . . . . ? C38A C39 C38B C60 62(2) . . . . ? C38A C39 C38B C37B -96(3) . . . . ? C38A C37A C42A C43A 81.4(8) . . . . ? C38A C60 C38B C39 -74(2) . . . . ? C38A C60 C38B C37B 83(3) . . . . ? C93 O7 C94 C95 19.8(5) . . . . ? C93 O7 C94 C99 -160.8(3) . . . . ? C93 C71B C70B C69B 180.0(5) . . . . ? C93 C71B C70B C75B -0.2(8) . . . . ? C2 C1 C13 O1 -107.3(3) . . . . ? C2 C3 C20 O2 68.6(3) . . . . ? C2 C3 C4 C5 6.3(4) . . . . ? C2 C3 C4 C9 -176.4(3) . . . . ? C60 O4 C61 C66 -21.1(5) . . . . ? C60 O4 C61 C62 159.5(3) . . . . ? C10 C9 C4 C5 86.7(4) . . . . ? C10 C9 C4 C3 -90.6(4) . . . . ? C42A C37A C38A C39 178.9(6) . . . . ? C42A C37A C38A C60 -7.4(9) . . . . ? C75A C70A C71A C72 -179.1(18) . . . . ? C75A C70A C71A C93 -32(2) . . . . ? C75A C70A C69A C68 178.6(16) . . . . ? C75A C70A C69A C86 22(2) . . . . ? C42B C37B C36B C35 -175.1(15) . . . . ? C42B C37B C36B C53 -21.6(18) . . . . ? C42B C37B C38B C39 179.6(15) . . . . ? C42B C37B C38B C60 23(2) . . . . ? C76A C75A C70A C71A 99(2) . . . . ? C76A C75A C70A C69A -81(2) . . . . ? C36B C35 C34 C46 -168.4(7) . . . . ? C36B C35 C34 C39 17.3(8) . . . . ? C36B C35 C40 C41 73.3(8) . . . . ? C36B C35 C36A C37A -88.2(18) . . . . ? C36B C35 C36A C53 80.9(18) . . . . ? C36B C37B C42B C43B 85.2(18) . . . . ? C36B C37B C38B C39 0(2) . . . . ? C36B C37B C38B C60 -155.8(13) . . . . ? C38B C39 C38A C37A 84(3) . . . . ? C38B C39 C38A C60 -89(3) . . . . ? C38B C37B C42B C43B -94.0(17) . . . . ? C38B C37B C36B C35 4.1(19) . . . . ? C38B C37B C36B C53 157.6(14) . . . . ? C71A C72 C71B C70B -99(3) . . . . ? C71A C72 C71B C93 81(3) . . . . ? C71A C72 C77 C78 77.3(12) . . . . ? C71A C70A C69A C68 -1(3) . . . . ? C71A C70A C69A C86 -158.1(15) . . . . ? C69A C68 C73 C74 -72.9(10) . . . . ? C69A C68 C69B C70B 85(4) . . . . ? C69A C68 C69B C86 -92(4) . . . . ? C69A C70A C71A C72 1(3) . . . . ? C69A C70A C71A C93 147.3(17) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962409' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-gf-298K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-gf, 298 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Cl3 O3' _chemical_formula_sum 'C33 H33 Cl3 O3' _chemical_formula_weight 583.94 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/a 1' _space_group_name_Hall '-P 2yab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z' _cell_length_a 25.0300(11) _cell_length_b 13.4909(5) _cell_length_c 28.9380(11) _cell_angle_alpha 90.00 _cell_angle_beta 110.676(5) _cell_angle_gamma 90.00 _cell_volume 9142.3(6) _cell_formula_units_Z 12 _cell_measurement_reflns_used 8170 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.1435 _cell_measurement_theta_min 4.0014 _exptl_absorpt_coefficient_mu 0.332 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.95901 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 3672 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0692 _diffrn_reflns_av_unetI/netI 0.0859 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 74716 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.21 _diffrn_reflns_theta_min 4.03 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.880 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0026399000 _diffrn_orient_matrix_UB_12 0.0504312000 _diffrn_orient_matrix_UB_13 -0.0057946000 _diffrn_orient_matrix_UB_21 -0.0272037000 _diffrn_orient_matrix_UB_22 -0.0021777000 _diffrn_orient_matrix_UB_23 -0.0190440000 _diffrn_orient_matrix_UB_31 -0.0130592000 _diffrn_orient_matrix_UB_32 0.0147196000 _diffrn_orient_matrix_UB_33 0.0170299000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 9005 _reflns_number_total 21821 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.413 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.044 _refine_ls_extinction_coef 0.00000(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 1123 _refine_ls_number_reflns 21821 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1864 _refine_ls_R_factor_gt 0.0710 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.554 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0810P)^2^+0.5090P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1684 _refine_ls_wR_factor_ref 0.2235 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Sof(H86C)=Sof(H86D)=Sof(H93C)=Sof(H93D)=Sof(C75A)=Sof(H75C)=Sof(H75D)= Sof(C70A)=Sof(C76A)=Sof(H76D)=Sof(H76E)=Sof(H76F)=Sof(C71A)=Sof(C69A)=1-FVAR(1) Sof(C69B)=Sof(C71B)=Sof(C70B)=Sof(H86A)=Sof(H86B)=Sof(H93A)=Sof(H93B)= Sof(C75B)=Sof(H75A)=Sof(H75B)=Sof(C76B)=Sof(H76A)=Sof(H76B)=Sof(H76C)=FVAR(1) Sof(H53C)=Sof(H53D)=Sof(H60C)=Sof(H60D)=Sof(C37B)=Sof(C42B)=Sof(H42C)= Sof(H42D)=Sof(C43B)=Sof(H43D)=Sof(H43E)=Sof(H43F)=Sof(C36B)=Sof(C38B)=1-FVAR(2) Sof(C36A)=Sof(C37A)=Sof(H53A)=Sof(H53B)=Sof(C38A)=Sof(H60A)=Sof(H60B)= Sof(C43A)=Sof(H43A)=Sof(H43B)=Sof(H43C)=Sof(C42A)=Sof(H42A)=Sof(H42B)=FVAR(2) 3.a Secondary CH2 refined with riding coordinates: C46(H46A,H46B), C79(H79A,H79B), C27(H27A,H27B), C40(H40A,H40B), C11(H11A, H11B), C73(H73A,H73B), C44(H44A,H44B), C9(H9A,H9B), C13(H13A,H13B), C20(H20A, H20B), C53(H53A,H53B), C53(H53C,H53D), C77(H77A,H77B), C86(H86A,H86B), C86(H86C,H86D), C93(H93A,H93B), C93(H93C,H93D), C75B(H75A,H75B), C60(H60A, H60B), C60(H60C,H60D), C7(H7A,H7B), C42A(H42A,H42B), C75A(H75C,H75D), C42B(H42C,H42D) 3.b Aromatic/amide H refined with riding coordinates: C48(H48), C29(H29), C66(H66), C85(H85), C95(H95), C49(H49), C91(H91), C81(H81), C26(H26), C33(H33), C96(H96), C56(H56), C30(H30), C25(H25), C52(H52), C98(H98), C92(H92), C65(H65), C55(H55), C84(H84), C15(H15), C88(H88), C32(H32), C63(H63), C99(H99), C59(H59), C19(H19), C22(H22), C62(H62), C82(H82), C89(H89), C23(H23), C58(H58), C18(H18), C16(H16), C51(H51) 3.c Idealised Me refined as rotating group: C74(H74A,H74B,H74C), C12(H12A,H12B,H12C), C41(H41A,H41B,H41C), C45(H45A,H45B, H45C), C78(H78A,H78B,H78C), C8(H8A,H8B,H8C), C43A(H43A,H43B,H43C), C10(H10A, H10B,H10C), C76B(H76A,H76B,H76C), C76A(H76D,H76E,H76F), C43B(H43D,H43E,H43F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl4 Cl 0.39898(7) 0.00776(8) 0.14653(4) 0.1380(6) Uani 1 1 d . . . Cl2 Cl 0.40912(6) 0.00803(7) 0.48351(4) 0.1009(4) Uani 1 1 d . . . Cl7 Cl 0.60672(7) 0.99618(7) 0.18853(4) 0.1282(6) Uani 1 1 d . . . Cl9 Cl 0.71881(5) 0.18256(9) -0.18171(4) 0.0950(4) Uani 1 1 d . . . Cl3 Cl 0.28699(5) 0.81644(8) 0.85685(4) 0.0876(3) Uani 1 1 d . . . Cl5 Cl 0.26652(5) 0.84702(8) 0.50498(4) 0.0946(4) Uani 1 1 d . . . Cl1 Cl 0.77276(5) 1.03178(9) 0.72814(5) 0.1100(4) Uani 1 1 d . . . Cl6 Cl 0.78329(5) 1.04605(10) 0.39156(5) 0.1097(4) Uani 1 1 d . . . Cl8 Cl 0.22017(5) -0.05432(11) -0.05896(5) 0.1200(5) Uani 1 1 d . . . O3 O 0.38781(8) 0.70867(16) 0.70893(7) 0.0569(6) Uani 1 1 d . . . O9 O 0.60870(9) 0.30519(17) -0.04267(8) 0.0652(6) Uani 1 1 d . . . O5 O 0.38220(9) 0.70794(18) 0.37262(8) 0.0640(6) Uani 1 1 d . . . O1 O 0.57420(9) 0.76685(16) 0.65826(8) 0.0604(6) Uani 1 1 d . . . O8 O 0.41115(11) 0.22503(18) -0.00428(9) 0.0744(7) Uani 1 1 d A . . C28 C 0.36116(12) 0.7357(2) 0.74141(11) 0.0452(7) Uani 1 1 d . . . C80 C 0.63783(14) 0.2744(2) -0.07262(12) 0.0519(8) Uani 1 1 d . . . O4 O 0.41934(10) 0.41535(16) 0.22215(9) 0.0687(6) Uani 1 1 d B . . O2 O 0.43913(9) 0.41088(16) 0.56576(8) 0.0622(6) Uani 1 1 d . . . C47 C 0.35172(13) 0.7420(2) 0.40082(11) 0.0496(8) Uani 1 1 d . . . O6 O 0.58623(11) 0.78068(17) 0.34094(9) 0.0727(7) Uani 1 1 d B . . C46 C 0.35990(13) 0.7228(2) 0.32004(11) 0.0539(8) Uani 1 1 d . . . H46A H 0.3522 0.7925 0.3121 0.065 Uiso 1 1 calc . . R H46B H 0.3249 0.6856 0.3049 0.065 Uiso 1 1 calc . . R O7 O 0.58030(10) 0.58377(16) 0.11946(8) 0.0684(6) Uani 1 1 d A . . C79 C 0.63324(13) 0.2850(2) 0.00953(10) 0.0548(8) Uani 1 1 d . . . H79A H 0.6688 0.3209 0.0243 0.066 Uiso 1 1 calc . . R H79B H 0.6406 0.2147 0.0154 0.066 Uiso 1 1 calc . . R C35 C 0.45100(13) 0.7483(2) 0.30389(10) 0.0482(7) Uani 1 1 d . . . C48 C 0.29878(13) 0.7860(2) 0.38177(12) 0.0537(8) Uani 1 1 d . . . H48 H 0.2809 0.7940 0.3479 0.064 Uiso 1 1 calc . . R C27 C 0.36065(12) 0.7370(2) 0.65814(10) 0.0492(8) Uani 1 1 d . . . H27A H 0.3570 0.8085 0.6553 0.059 Uiso 1 1 calc . . R H27B H 0.3229 0.7079 0.6446 0.059 Uiso 1 1 calc . . R C67 C 0.58931(13) 0.3197(2) 0.03051(10) 0.0497(8) Uani 1 1 d A . . C68 C 0.54465(14) 0.2564(2) 0.02880(11) 0.0496(8) Uani 1 1 d . . . C14 C 0.61987(13) 0.8303(2) 0.67211(12) 0.0521(8) Uani 1 1 d . . . C61 C 0.41790(14) 0.3184(2) 0.20674(12) 0.0536(8) Uani 1 1 d . . . C5 C 0.39783(12) 0.6996(2) 0.63072(10) 0.0423(7) Uani 1 1 d . . . C87 C 0.36705(15) 0.1583(2) -0.01458(13) 0.0597(9) Uani 1 1 d . . . C29 C 0.30897(13) 0.7819(2) 0.72787(11) 0.0506(8) Uani 1 1 d . . . H29 H 0.2890 0.7971 0.6949 0.061 Uiso 1 1 calc . . R C34 C 0.40637(13) 0.6855(2) 0.30244(10) 0.0475(7) Uani 1 1 d B . . C6 C 0.44501(12) 0.7557(2) 0.63116(10) 0.0421(7) Uani 1 1 d . . . C66 C 0.46123(15) 0.2514(2) 0.22554(12) 0.0585(8) Uani 1 1 d . . . H66 H 0.4944 0.2700 0.2510 0.070 Uiso 1 1 calc . . R C85 C 0.68987(13) 0.2275(2) -0.05630(12) 0.0560(8) Uani 1 1 d . . . H85 H 0.7083 0.2146 -0.0229 0.067 Uiso 1 1 calc . . R C21 C 0.42937(13) 0.3196(2) 0.54270(11) 0.0471(7) Uani 1 1 d . . . C54 C 0.63178(14) 0.8429(2) 0.34979(13) 0.0560(8) Uani 1 1 d . . . C95 C 0.54156(15) 0.7511(2) 0.11333(12) 0.0630(9) Uani 1 1 d . . . H95 H 0.5084 0.7333 0.0875 0.076 Uiso 1 1 calc . . R C40 C 0.45135(14) 0.8556(2) 0.31973(11) 0.0579(8) Uani 1 1 d B . . H40A H 0.4905 0.8767 0.3363 0.070 Uiso 1 1 calc . . R H40B H 0.4318 0.8605 0.3433 0.070 Uiso 1 1 calc . . R C49 C 0.27245(14) 0.8185(2) 0.41432(14) 0.0616(9) Uani 1 1 d . . . H49 H 0.2366 0.8481 0.4020 0.074 Uiso 1 1 calc . . R C91 C 0.30952(18) 0.0395(3) 0.00683(14) 0.0852(12) Uani 1 1 d . . . H91 H 0.3012 0.0029 0.0307 0.102 Uiso 1 1 calc . . R C94 C 0.58326(14) 0.6818(2) 0.13383(12) 0.0519(8) Uani 1 1 d . . . C81 C 0.61075(15) 0.2933(3) -0.12223(12) 0.0673(10) Uani 1 1 d . . . H81 H 0.5756 0.3252 -0.1332 0.081 Uiso 1 1 calc . . R C11 C 0.45596(14) 0.8567(2) 0.65485(11) 0.0544(8) Uani 1 1 d . . . H11A H 0.4967 0.8695 0.6676 0.065 Uiso 1 1 calc . . R H11B H 0.4424 0.8582 0.6824 0.065 Uiso 1 1 calc . . R C26 C 0.47208(14) 0.2513(2) 0.56259(11) 0.0581(8) Uani 1 1 d . . . H26 H 0.5049 0.2690 0.5887 0.070 Uiso 1 1 calc . . R C33 C 0.39012(14) 0.7130(3) 0.79024(11) 0.0612(9) Uani 1 1 d . . . H33 H 0.4253 0.6811 0.7993 0.073 Uiso 1 1 calc . . R C96 C 0.54862(18) 0.8474(3) 0.13095(13) 0.0746(11) Uani 1 1 d . . . H96 H 0.5200 0.8940 0.1171 0.090 Uiso 1 1 calc . . R C56 C 0.69069(15) 0.9571(3) 0.32675(13) 0.0703(10) Uani 1 1 d . . . H56 H 0.6993 0.9926 0.3027 0.084 Uiso 1 1 calc . . R C30 C 0.28631(14) 0.8058(2) 0.76395(12) 0.0562(8) Uani 1 1 d . . . H30 H 0.2509 0.8367 0.7551 0.067 Uiso 1 1 calc . . R C72 C 0.59081(14) 0.4181(2) 0.04733(11) 0.0547(8) Uani 1 1 d . . . C90 C 0.27684(16) 0.0288(3) -0.04195(15) 0.0727(10) Uani 1 1 d . . . C25 C 0.46602(16) 0.1562(3) 0.54354(12) 0.0665(10) Uani 1 1 d . . . H25 H 0.4950 0.1100 0.5568 0.080 Uiso 1 1 calc . . R C52 C 0.37780(14) 0.7305(3) 0.45095(12) 0.0625(9) Uani 1 1 d . . . H52 H 0.4135 0.7004 0.4635 0.075 Uiso 1 1 calc . . R C73 C 0.54205(15) 0.1513(2) 0.00964(11) 0.0614(9) Uani 1 1 d A . . H73A H 0.5593 0.1495 -0.0155 0.074 Uiso 1 1 calc . . R H73B H 0.5024 0.1318 -0.0057 0.074 Uiso 1 1 calc . . R C74 C 0.57259(18) 0.0766(3) 0.05029(14) 0.0880(12) Uani 1 1 d . . . H74A H 0.5667 0.0108 0.0368 0.132 Uiso 1 1 calc A . GR H74B H 0.5575 0.0813 0.0764 0.132 Uiso 1 1 calc . . GR H74C H 0.6127 0.0909 0.0631 0.132 Uiso 1 1 calc . . GR C44 C 0.35534(13) 0.5200(2) 0.28288(13) 0.0617(9) Uani 1 1 d B . . H44A H 0.3415 0.5328 0.3097 0.074 Uiso 1 1 calc . . R H44B H 0.3669 0.4510 0.2849 0.074 Uiso 1 1 calc . . R C64 C 0.4069(2) 0.1289(3) 0.16929(13) 0.0739(11) Uani 1 1 d . . . C98 C 0.63917(17) 0.8055(3) 0.18887(13) 0.0721(11) Uani 1 1 d . . . H98 H 0.6724 0.8238 0.2144 0.087 Uiso 1 1 calc . . R C92 C 0.35434(17) 0.1038(3) 0.02054(13) 0.0786(12) Uani 1 1 d . . . H92 H 0.3765 0.1110 0.0538 0.094 Uiso 1 1 calc . . R C65 C 0.45579(18) 0.1559(3) 0.20669(13) 0.0747(11) Uani 1 1 d . . . H65 H 0.4853 0.1105 0.2194 0.090 Uiso 1 1 calc . . R C83 C 0.68721(15) 0.2178(2) -0.13927(13) 0.0581(9) Uani 1 1 d . . . C57 C 0.72464(14) 0.9658(3) 0.37580(14) 0.0644(9) Uani 1 1 d . . . C55 C 0.64385(15) 0.8952(3) 0.31379(12) 0.0670(10) Uani 1 1 d . . . H55 H 0.6205 0.8889 0.2808 0.080 Uiso 1 1 calc . . R C50 C 0.29887(15) 0.8073(2) 0.46388(13) 0.0568(9) Uani 1 1 d . . . C1 C 0.47994(12) 0.7193(2) 0.60643(11) 0.0460(7) Uani 1 1 d . . . C84 C 0.71445(14) 0.1997(2) -0.09027(13) 0.0609(9) Uani 1 1 d . . . H84 H 0.7498 0.1684 -0.0796 0.073 Uiso 1 1 calc . . R C15 C 0.63398(15) 0.8924(3) 0.64031(12) 0.0673(10) Uani 1 1 d . . . H15 H 0.6118 0.8927 0.6069 0.081 Uiso 1 1 calc . . R C88 C 0.33404(17) 0.1463(3) -0.06368(13) 0.0700(10) Uani 1 1 d . . . H88 H 0.3422 0.1827 -0.0877 0.084 Uiso 1 1 calc . . R C32 C 0.36749(15) 0.7372(3) 0.82568(12) 0.0627(9) Uani 1 1 d . . . H32 H 0.3872 0.7217 0.8586 0.075 Uiso 1 1 calc . . R C17 C 0.71364(14) 0.9538(3) 0.70681(15) 0.0650(9) Uani 1 1 d . . . C63 C 0.36335(18) 0.1954(3) 0.14992(13) 0.0772(11) Uani 1 1 d . . . H63 H 0.3302 0.1765 0.1244 0.093 Uiso 1 1 calc . . R C31 C 0.31575(14) 0.7842(2) 0.81216(12) 0.0546(8) Uani 1 1 d . . . C99 C 0.63218(15) 0.7101(3) 0.17178(13) 0.0648(9) Uani 1 1 d . . . H99 H 0.6608 0.6637 0.1859 0.078 Uiso 1 1 calc . . R C24 C 0.41748(16) 0.1299(2) 0.50517(12) 0.0583(9) Uani 1 1 d . . . C59 C 0.66621(16) 0.8521(3) 0.39853(13) 0.0679(10) Uani 1 1 d . . . H59 H 0.6582 0.8162 0.4228 0.081 Uiso 1 1 calc . . R C69B C 0.4974(3) 0.2923(5) 0.0414(3) 0.0501(16) Uani 0.717(12) 1 d A 3 . C19 C 0.65297(15) 0.8316(3) 0.72125(13) 0.0661(10) Uani 1 1 d . . . H19 H 0.6438 0.7901 0.7430 0.079 Uiso 1 1 calc . . R C36A C 0.5012(3) 0.7086(5) 0.2979(3) 0.0461(17) Uani 0.609(17) 1 d B 1 . C22 C 0.38150(13) 0.2942(2) 0.50299(11) 0.0533(8) Uani 1 1 d . . . H22 H 0.3533 0.3412 0.4887 0.064 Uiso 1 1 calc . . R C39 C 0.40666(13) 0.5855(2) 0.28898(11) 0.0495(8) Uani 1 1 d . . . C12 C 0.42583(16) 0.9371(2) 0.61773(14) 0.0762(11) Uani 1 1 d . . . H12A H 0.4340 1.0008 0.6335 0.114 Uiso 1 1 calc . . GR H12B H 0.3854 0.9257 0.6059 0.114 Uiso 1 1 calc . . GR H12C H 0.4392 0.9355 0.5905 0.114 Uiso 1 1 calc . . GR C9 C 0.33330(13) 0.5499(2) 0.60550(12) 0.0591(9) Uani 1 1 d . . . H9A H 0.3288 0.5581 0.6372 0.071 Uiso 1 1 calc . . R H9B H 0.3402 0.4802 0.6016 0.071 Uiso 1 1 calc . . R C97 C 0.5970(2) 0.8742(3) 0.16825(13) 0.0713(11) Uani 1 1 d . . . C71B C 0.5415(3) 0.4551(4) 0.0578(2) 0.0427(14) Uani 0.717(12) 1 d A 3 . C3 C 0.41737(13) 0.5770(2) 0.57782(11) 0.0500(8) Uani 1 1 d . . . C62 C 0.36898(16) 0.2906(3) 0.16844(13) 0.0675(10) Uani 1 1 d . . . H62 H 0.3397 0.3363 0.1551 0.081 Uiso 1 1 calc . . R C41 C 0.42256(17) 0.9254(3) 0.27634(14) 0.0812(11) Uani 1 1 d . . . H41A H 0.4411 0.9198 0.2525 0.122 Uiso 1 1 calc B . GR H41B H 0.4255 0.9924 0.2881 0.122 Uiso 1 1 calc . . GR H41C H 0.3830 0.9077 0.2612 0.122 Uiso 1 1 calc . . GR C13 C 0.53215(13) 0.7790(2) 0.60900(11) 0.0567(8) Uani 1 1 d . . . H13A H 0.5474 0.7555 0.5845 0.068 Uiso 1 1 calc . . R H13B H 0.5222 0.8484 0.6026 0.068 Uiso 1 1 calc . . R C82 C 0.63582(15) 0.2649(3) -0.15565(12) 0.0673(10) Uani 1 1 d . . . H82 H 0.6177 0.2778 -0.1891 0.081 Uiso 1 1 calc . . R C89 C 0.28937(17) 0.0812(3) -0.07712(14) 0.0762(11) Uani 1 1 d . . . H89 H 0.2675 0.0726 -0.1103 0.091 Uiso 1 1 calc . . R C23 C 0.37562(15) 0.1986(3) 0.48448(12) 0.0592(9) Uani 1 1 d . . . H23 H 0.3432 0.1810 0.4579 0.071 Uiso 1 1 calc . . R C58 C 0.71244(16) 0.9145(3) 0.41123(13) 0.0695(10) Uani 1 1 d . . . H58 H 0.7355 0.9217 0.4442 0.083 Uiso 1 1 calc . . R C18 C 0.69969(15) 0.8937(3) 0.73899(13) 0.0705(10) Uani 1 1 d . . . H18 H 0.7215 0.8947 0.7725 0.085 Uiso 1 1 calc . . R C45 C 0.30727(15) 0.5380(3) 0.23380(14) 0.0837(12) Uani 1 1 d . . . H45A H 0.3193 0.5175 0.2072 0.126 Uiso 1 1 calc B . GR H45B H 0.2980 0.6073 0.2305 0.126 Uiso 1 1 calc . . GR H45C H 0.2742 0.5006 0.2328 0.126 Uiso 1 1 calc . . GR C20 C 0.39953(14) 0.4861(2) 0.54519(12) 0.0600(9) Uani 1 1 d . . . H20A H 0.3617 0.4650 0.5431 0.072 Uiso 1 1 calc . . R H20B H 0.3985 0.5014 0.5121 0.072 Uiso 1 1 calc . . R C16 C 0.68066(16) 0.9536(3) 0.65775(14) 0.0760(11) Uani 1 1 d . . . H16 H 0.6899 0.9953 0.6361 0.091 Uiso 1 1 calc . . R C37A C 0.5045(4) 0.6069(5) 0.2885(4) 0.0416(17) Uani 0.609(17) 1 d B 1 . C51 C 0.35167(15) 0.7630(3) 0.48267(13) 0.0629(9) Uani 1 1 d . . . H51 H 0.3696 0.7552 0.5166 0.075 Uiso 1 1 calc . . R C53 C 0.54443(15) 0.7801(3) 0.29197(14) 0.0690(10) Uani 1 1 d . . . H53A H 0.5605 0.7566 0.2680 0.083 Uiso 0.609(17) 1 calc B 1 R H53B H 0.5280 0.8454 0.2823 0.083 Uiso 0.609(17) 1 calc B 1 R H53C H 0.5633 0.7573 0.2699 0.083 Uiso 0.391(17) 1 calc B 2 R H53D H 0.5332 0.8483 0.2831 0.083 Uiso 0.391(17) 1 calc B 2 R C4 C 0.38454(12) 0.6094(2) 0.60518(10) 0.0479(7) Uani 1 1 d . . . C70B C 0.4956(3) 0.3931(4) 0.0543(2) 0.0500(16) Uani 0.717(12) 1 d A 3 . C77 C 0.64224(15) 0.4832(2) 0.05320(12) 0.0646(9) Uani 1 1 d A . . H77A H 0.6550 0.4718 0.0257 0.078 Uiso 1 1 calc . . R H77B H 0.6311 0.5523 0.0523 0.078 Uiso 1 1 calc . . R C86 C 0.45349(16) 0.2223(3) 0.04419(14) 0.0684(10) Uani 1 1 d . . . H86A H 0.4692 0.1562 0.0523 0.082 Uiso 0.717(12) 1 calc A 3 R H86B H 0.4377 0.2434 0.0687 0.082 Uiso 0.717(12) 1 calc A 3 R H86C H 0.4639 0.1535 0.0520 0.082 Uiso 0.283(12) 1 calc A 4 R H86D H 0.4354 0.2446 0.0670 0.082 Uiso 0.283(12) 1 calc A 4 R C38A C 0.4583(4) 0.5447(5) 0.2845(3) 0.0400(17) Uani 0.609(17) 1 d B 1 . C78 C 0.69115(17) 0.4629(3) 0.10119(14) 0.0876(12) Uani 1 1 d . . . H78A H 0.7028 0.3949 0.1019 0.131 Uiso 1 1 calc A . GR H78B H 0.6789 0.4754 0.1286 0.131 Uiso 1 1 calc . . GR H78C H 0.7227 0.5054 0.1035 0.131 Uiso 1 1 calc . . GR C93 C 0.54091(16) 0.5623(3) 0.07148(14) 0.0726(10) Uani 1 1 d . . . H93A H 0.5500 0.6026 0.0475 0.087 Uiso 0.717(12) 1 calc A 3 R H93B H 0.5028 0.5800 0.0700 0.087 Uiso 0.717(12) 1 calc A 3 R H93C H 0.5484 0.5996 0.0458 0.087 Uiso 0.283(12) 1 calc A 4 R H93D H 0.5015 0.5708 0.0689 0.087 Uiso 0.283(12) 1 calc A 4 R C8 C 0.55809(15) 0.5433(3) 0.58676(15) 0.0788(11) Uani 1 1 d . . . H8A H 0.5795 0.5902 0.6113 0.118 Uiso 1 1 calc . . GR H8B H 0.5808 0.5212 0.5681 0.118 Uiso 1 1 calc . . GR H8C H 0.5481 0.4876 0.6027 0.118 Uiso 1 1 calc . . GR C2 C 0.46648(12) 0.6306(2) 0.57927(10) 0.0469(7) Uani 1 1 d . . . C75B C 0.4444(3) 0.4322(4) 0.0651(2) 0.0654(18) Uani 0.717(12) 1 d A 3 . H75A H 0.4346 0.4976 0.0507 0.078 Uiso 0.717(12) 1 calc A 3 R H75B H 0.4120 0.3889 0.0501 0.078 Uiso 0.717(12) 1 calc A 3 R C60 C 0.45882(15) 0.4382(2) 0.27035(13) 0.0664(9) Uani 1 1 d . . . H60A H 0.4970 0.4209 0.2718 0.080 Uiso 0.609(17) 1 calc B 1 R H60B H 0.4499 0.3975 0.2943 0.080 Uiso 0.609(17) 1 calc B 1 R H60C H 0.4980 0.4241 0.2737 0.080 Uiso 0.391(17) 1 calc B 2 R H60D H 0.4495 0.4046 0.2962 0.080 Uiso 0.391(17) 1 calc B 2 R C7 C 0.50439(13) 0.5921(2) 0.55253(11) 0.0560(8) Uani 1 1 d . . . H7A H 0.4831 0.5445 0.5277 0.067 Uiso 1 1 calc . . R H7B H 0.5148 0.6467 0.5356 0.067 Uiso 1 1 calc . . R C43A C 0.5530(5) 0.5511(7) 0.2301(3) 0.081(3) Uani 0.609(17) 1 d B 1 . H43A H 0.5436 0.6135 0.2132 0.122 Uiso 0.609(17) 1 calc B 1 GR H43B H 0.5231 0.5042 0.2148 0.122 Uiso 0.609(17) 1 calc B 1 GR H43C H 0.5882 0.5270 0.2282 0.122 Uiso 0.609(17) 1 calc B 1 GR C10 C 0.27813(15) 0.5812(3) 0.56460(13) 0.0782(11) Uani 1 1 d . . . H10A H 0.2710 0.6501 0.5683 0.117 Uiso 1 1 calc . . GR H10B H 0.2469 0.5424 0.5667 0.117 Uiso 1 1 calc . . GR H10C H 0.2818 0.5707 0.5330 0.117 Uiso 1 1 calc . . GR C76B C 0.4568(3) 0.4382(5) 0.1200(2) 0.087(2) Uani 0.717(12) 1 d A 3 . H76A H 0.4227 0.4565 0.1258 0.131 Uiso 0.717(12) 1 calc A 3 GR H76B H 0.4859 0.4870 0.1343 0.131 Uiso 0.717(12) 1 calc A 3 GR H76C H 0.4698 0.3748 0.1347 0.131 Uiso 0.717(12) 1 calc A 3 GR C42A C 0.5594(4) 0.5649(5) 0.2846(3) 0.053(2) Uani 0.609(17) 1 d B 1 . H42A H 0.5680 0.5016 0.3016 0.064 Uiso 0.609(17) 1 calc B 1 R H42B H 0.5909 0.6098 0.3005 0.064 Uiso 0.609(17) 1 calc B 1 R C75A C 0.4811(6) 0.4055(11) 0.1075(5) 0.061(5) Uiso 0.283(12) 1 d A 4 . H75C H 0.5005 0.4570 0.1308 0.074 Uiso 0.283(12) 1 calc A 4 R H75D H 0.4775 0.3482 0.1264 0.074 Uiso 0.283(12) 1 calc A 4 R C37B C 0.4869(6) 0.6219(9) 0.2634(7) 0.051(3) Uani 0.391(17) 1 d B 2 . C42B C 0.5291(6) 0.5868(9) 0.2415(6) 0.075(5) Uani 0.391(17) 1 d B 2 . H42C H 0.5351 0.6398 0.2212 0.090 Uiso 0.391(17) 1 calc B 2 R H42D H 0.5123 0.5316 0.2198 0.090 Uiso 0.391(17) 1 calc B 2 R C70A C 0.5178(7) 0.3776(10) 0.0780(6) 0.048(4) Uiso 0.283(12) 1 d A 4 . C76A C 0.4196(8) 0.4432(13) 0.0762(7) 0.083(6) Uiso 0.283(12) 1 d A 4 . H76D H 0.3983 0.3903 0.0557 0.124 Uiso 0.283(12) 1 calc A 4 GR H76E H 0.4224 0.4976 0.0557 0.124 Uiso 0.283(12) 1 calc A 4 GR H76F H 0.4005 0.4647 0.0979 0.124 Uiso 0.283(12) 1 calc A 4 GR C43B C 0.5873(8) 0.5542(12) 0.2772(9) 0.129(7) Uani 0.391(17) 1 d B 2 . H43D H 0.6114 0.5367 0.2589 0.194 Uiso 0.391(17) 1 calc B 2 GR H43E H 0.5828 0.4978 0.2957 0.194 Uiso 0.391(17) 1 calc B 2 GR H43F H 0.6046 0.6075 0.2994 0.194 Uiso 0.391(17) 1 calc B 2 GR C36B C 0.4886(5) 0.7181(8) 0.2805(4) 0.033(3) Uiso 0.391(17) 1 d B 2 . C38B C 0.4459(6) 0.5553(10) 0.2686(5) 0.048(4) Uiso 0.391(17) 1 d B 2 . C71A C 0.5598(9) 0.4428(16) 0.0728(8) 0.071(7) Uiso 0.283(12) 1 d A 4 . C69A C 0.5130(7) 0.2855(14) 0.0564(6) 0.039(5) Uiso 0.283(12) 1 d A 4 . 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 Cl4 0.2679(18) 0.0529(6) 0.0653(7) -0.0140(5) 0.0243(9) -0.0249(9) Cl2 0.1807(12) 0.0428(5) 0.0683(6) -0.0109(5) 0.0302(7) -0.0040(7) Cl7 0.2388(16) 0.0503(6) 0.0714(7) -0.0157(5) 0.0247(8) -0.0345(8) Cl9 0.0998(8) 0.1149(9) 0.0947(7) -0.0009(6) 0.0647(7) 0.0152(7) Cl3 0.0989(8) 0.1057(8) 0.0834(7) -0.0124(6) 0.0633(6) 0.0030(6) Cl5 0.1122(9) 0.0960(8) 0.1067(8) 0.0069(6) 0.0773(7) 0.0218(7) Cl1 0.0782(8) 0.1087(9) 0.1200(9) -0.0099(7) 0.0062(7) -0.0392(7) Cl6 0.0735(7) 0.1306(11) 0.1106(9) -0.0265(8) 0.0146(6) -0.0425(7) Cl8 0.0986(9) 0.1292(11) 0.1138(9) -0.0233(8) 0.0149(7) -0.0476(8) O3 0.0543(13) 0.0773(16) 0.0430(12) 0.0020(11) 0.0221(10) 0.0216(11) O9 0.0676(15) 0.0827(17) 0.0485(13) 0.0057(12) 0.0247(11) 0.0227(13) O5 0.0569(14) 0.0899(18) 0.0482(13) 0.0069(12) 0.0222(11) 0.0231(12) O1 0.0530(14) 0.0614(15) 0.0660(14) 0.0118(12) 0.0200(11) -0.0107(12) O8 0.0863(19) 0.0664(17) 0.0740(17) 0.0080(13) 0.0326(15) -0.0167(15) C28 0.0461(18) 0.0461(18) 0.0472(18) -0.0043(14) 0.0213(15) 0.0018(15) C80 0.056(2) 0.049(2) 0.056(2) -0.0037(16) 0.0253(17) -0.0010(16) O4 0.0804(17) 0.0443(14) 0.0770(16) -0.0056(12) 0.0225(14) 0.0020(13) O2 0.0618(15) 0.0398(13) 0.0751(15) -0.0071(11) 0.0117(12) 0.0052(12) C47 0.0498(19) 0.051(2) 0.0522(19) 0.0032(16) 0.0236(16) 0.0047(16) O6 0.0773(18) 0.0655(17) 0.0830(18) 0.0002(13) 0.0378(15) -0.0220(14) C46 0.0512(19) 0.059(2) 0.0482(18) 0.0037(16) 0.0138(15) 0.0049(16) O7 0.0890(18) 0.0470(14) 0.0692(15) -0.0093(12) 0.0281(14) -0.0035(13) C79 0.062(2) 0.059(2) 0.0419(17) -0.0022(15) 0.0165(15) 0.0018(17) C35 0.055(2) 0.0418(18) 0.0474(18) -0.0053(14) 0.0170(15) -0.0025(16) C48 0.051(2) 0.051(2) 0.059(2) 0.0004(16) 0.0181(16) 0.0029(16) C27 0.0465(18) 0.057(2) 0.0430(17) -0.0038(15) 0.0141(14) 0.0065(15) C67 0.062(2) 0.0455(19) 0.0435(17) -0.0030(14) 0.0203(15) -0.0020(16) C68 0.066(2) 0.0385(18) 0.0451(18) -0.0016(14) 0.0204(16) -0.0007(16) C14 0.0469(19) 0.053(2) 0.059(2) 0.0009(17) 0.0220(16) -0.0017(16) C61 0.062(2) 0.044(2) 0.0554(19) -0.0005(16) 0.0217(17) -0.0048(17) C5 0.0465(18) 0.0444(18) 0.0376(16) -0.0062(13) 0.0167(13) 0.0016(14) C87 0.071(2) 0.050(2) 0.066(2) -0.0043(18) 0.035(2) -0.0033(18) C29 0.0505(19) 0.052(2) 0.0510(18) -0.0040(15) 0.0203(15) 0.0058(16) C34 0.0504(19) 0.0468(19) 0.0459(17) -0.0026(14) 0.0179(14) -0.0009(16) C6 0.0471(18) 0.0356(16) 0.0431(16) -0.0036(13) 0.0154(14) -0.0020(14) C66 0.066(2) 0.044(2) 0.059(2) -0.0010(16) 0.0136(17) -0.0005(18) C85 0.057(2) 0.053(2) 0.058(2) 0.0017(16) 0.0205(17) 0.0063(17) C21 0.054(2) 0.0406(18) 0.0503(18) -0.0057(15) 0.0234(16) -0.0037(16) C54 0.064(2) 0.0430(19) 0.072(2) -0.0049(17) 0.0368(19) -0.0058(17) C95 0.072(2) 0.046(2) 0.062(2) -0.0081(17) 0.0128(18) -0.0018(19) C40 0.065(2) 0.0457(19) 0.060(2) -0.0108(16) 0.0179(17) -0.0022(17) C49 0.048(2) 0.055(2) 0.085(3) 0.0036(19) 0.0282(19) 0.0058(17) C91 0.104(3) 0.087(3) 0.068(3) -0.010(2) 0.035(2) -0.043(3) C94 0.066(2) 0.0424(19) 0.0542(19) -0.0025(16) 0.0305(17) -0.0070(18) C81 0.066(2) 0.088(3) 0.053(2) 0.0057(19) 0.0262(18) 0.019(2) C11 0.060(2) 0.0448(19) 0.058(2) -0.0129(16) 0.0205(16) -0.0034(16) C26 0.067(2) 0.047(2) 0.0506(19) -0.0021(16) 0.0092(16) 0.0044(18) C33 0.061(2) 0.077(3) 0.049(2) 0.0037(17) 0.0235(17) 0.0136(18) C96 0.106(3) 0.044(2) 0.062(2) -0.0029(18) 0.016(2) 0.003(2) C56 0.078(3) 0.076(3) 0.064(2) -0.005(2) 0.034(2) -0.023(2) C30 0.051(2) 0.055(2) 0.070(2) -0.0092(17) 0.0307(18) 0.0019(16) C72 0.072(2) 0.046(2) 0.0502(19) -0.0034(15) 0.0262(17) -0.0121(17) C90 0.072(3) 0.070(3) 0.073(3) -0.011(2) 0.022(2) -0.011(2) C25 0.089(3) 0.045(2) 0.060(2) 0.0048(17) 0.019(2) 0.013(2) C52 0.057(2) 0.074(3) 0.059(2) 0.0096(18) 0.0248(18) 0.0193(18) C73 0.074(2) 0.047(2) 0.059(2) -0.0130(17) 0.0175(18) 0.0009(18) C74 0.109(3) 0.043(2) 0.094(3) 0.004(2) 0.013(3) 0.007(2) C44 0.062(2) 0.051(2) 0.078(2) 0.0077(18) 0.0310(19) -0.0112(17) C64 0.129(4) 0.043(2) 0.048(2) -0.0043(17) 0.029(2) -0.012(2) C98 0.080(3) 0.074(3) 0.056(2) -0.011(2) 0.017(2) -0.030(2) C92 0.101(3) 0.085(3) 0.050(2) -0.009(2) 0.027(2) -0.040(2) C65 0.105(3) 0.052(2) 0.058(2) -0.0003(18) 0.017(2) 0.007(2) C83 0.063(2) 0.057(2) 0.065(2) -0.0059(18) 0.0353(19) -0.0057(18) C57 0.053(2) 0.070(2) 0.065(2) -0.013(2) 0.0145(18) -0.0030(18) C55 0.074(2) 0.075(3) 0.055(2) -0.0086(18) 0.0259(18) -0.029(2) C50 0.061(2) 0.048(2) 0.072(2) 0.0015(17) 0.0369(19) -0.0023(17) C1 0.0482(18) 0.0403(18) 0.0521(18) 0.0011(14) 0.0210(15) -0.0002(15) C84 0.053(2) 0.057(2) 0.077(3) -0.0014(18) 0.0285(19) 0.0051(17) C15 0.078(3) 0.073(3) 0.054(2) -0.0041(18) 0.0273(18) -0.028(2) C88 0.083(3) 0.072(3) 0.057(2) 0.013(2) 0.028(2) 0.014(2) C32 0.071(2) 0.077(3) 0.0428(18) -0.0006(17) 0.0241(17) 0.002(2) C17 0.055(2) 0.056(2) 0.082(3) -0.006(2) 0.022(2) -0.0079(18) C63 0.093(3) 0.074(3) 0.052(2) -0.002(2) 0.010(2) -0.027(2) C31 0.061(2) 0.055(2) 0.058(2) -0.0125(17) 0.0347(18) -0.0076(17) C99 0.064(2) 0.063(2) 0.066(2) -0.0014(19) 0.0220(19) -0.0038(19) C24 0.094(3) 0.0401(19) 0.0462(19) -0.0048(15) 0.0307(19) -0.0045(19) C59 0.072(3) 0.075(3) 0.060(2) 0.013(2) 0.027(2) 0.010(2) C69B 0.059(4) 0.039(3) 0.047(4) 0.000(3) 0.012(3) -0.009(3) C19 0.057(2) 0.073(3) 0.067(2) 0.018(2) 0.0197(19) 0.002(2) C36A 0.053(4) 0.045(4) 0.030(4) 0.005(3) 0.003(3) -0.004(3) C22 0.054(2) 0.049(2) 0.056(2) -0.0045(16) 0.0191(16) -0.0003(16) C39 0.055(2) 0.0468(19) 0.0496(18) 0.0013(15) 0.0212(15) -0.0075(16) C12 0.091(3) 0.040(2) 0.092(3) -0.0017(19) 0.025(2) 0.008(2) C9 0.057(2) 0.059(2) 0.065(2) -0.0046(17) 0.0269(18) -0.0159(17) C97 0.119(3) 0.045(2) 0.048(2) -0.0074(17) 0.028(2) -0.021(2) C71B 0.051(4) 0.029(3) 0.043(3) -0.006(2) 0.010(3) -0.002(3) C3 0.056(2) 0.0442(19) 0.0503(18) -0.0067(15) 0.0200(15) -0.0030(16) C62 0.067(2) 0.068(3) 0.062(2) 0.0082(19) 0.0163(19) -0.002(2) C41 0.102(3) 0.046(2) 0.084(3) 0.007(2) 0.018(2) 0.006(2) C13 0.056(2) 0.060(2) 0.056(2) 0.0015(17) 0.0219(17) -0.0090(17) C82 0.072(3) 0.082(3) 0.051(2) 0.0024(19) 0.0251(18) 0.006(2) C89 0.080(3) 0.082(3) 0.058(2) -0.006(2) 0.013(2) 0.007(2) C23 0.066(2) 0.056(2) 0.055(2) -0.0106(17) 0.0213(17) -0.0110(19) C58 0.070(3) 0.079(3) 0.051(2) 0.000(2) 0.0110(19) 0.014(2) C18 0.059(2) 0.079(3) 0.061(2) 0.006(2) 0.0067(18) 0.006(2) C45 0.069(3) 0.076(3) 0.090(3) -0.003(2) 0.007(2) -0.019(2) C20 0.055(2) 0.064(2) 0.058(2) -0.0114(18) 0.0159(16) -0.0019(18) C16 0.082(3) 0.079(3) 0.073(3) -0.008(2) 0.034(2) -0.036(2) C37A 0.049(4) 0.041(4) 0.035(4) 0.005(3) 0.014(3) 0.000(3) C51 0.072(2) 0.065(2) 0.056(2) 0.0056(18) 0.0285(18) 0.004(2) C53 0.072(3) 0.056(2) 0.096(3) -0.020(2) 0.051(2) -0.0236(19) C4 0.0505(19) 0.0467(19) 0.0477(17) -0.0045(15) 0.0188(15) -0.0086(15) C70B 0.056(4) 0.044(3) 0.048(4) -0.003(2) 0.017(3) -0.003(3) C77 0.081(3) 0.053(2) 0.064(2) -0.0026(17) 0.0294(19) -0.0180(19) C86 0.083(3) 0.050(2) 0.085(3) -0.0062(19) 0.045(2) -0.014(2) C38A 0.050(4) 0.034(3) 0.030(4) 0.004(3) 0.007(3) 0.003(3) C78 0.092(3) 0.080(3) 0.079(3) -0.005(2) 0.016(2) -0.026(2) C93 0.080(3) 0.055(2) 0.081(3) -0.014(2) 0.027(2) -0.012(2) C8 0.060(2) 0.081(3) 0.100(3) 0.007(2) 0.033(2) 0.018(2) C2 0.0507(19) 0.0479(19) 0.0459(17) -0.0019(15) 0.0218(15) 0.0020(15) C75B 0.068(4) 0.061(3) 0.072(4) 0.001(3) 0.030(3) -0.002(3) C60 0.067(2) 0.052(2) 0.079(2) -0.0134(19) 0.024(2) -0.0092(18) C7 0.063(2) 0.059(2) 0.0535(19) -0.0062(16) 0.0295(17) 0.0015(18) C43A 0.081(6) 0.090(6) 0.081(6) -0.026(4) 0.041(5) -0.014(5) C10 0.062(2) 0.088(3) 0.072(2) -0.003(2) 0.0081(19) -0.018(2) C76B 0.105(5) 0.096(5) 0.073(4) 0.002(3) 0.046(4) 0.001(4) C42A 0.054(5) 0.048(4) 0.058(5) -0.001(3) 0.021(4) 0.002(3) C37B 0.048(7) 0.054(7) 0.052(8) -0.003(6) 0.020(6) 0.005(5) C42B 0.082(9) 0.054(7) 0.111(12) -0.015(7) 0.061(9) -0.002(6) C43B 0.071(11) 0.104(11) 0.22(2) -0.028(12) 0.058(13) 0.011(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 Cl4 C64 1.747(3) . ? Cl2 C24 1.745(3) . ? Cl7 C97 1.735(3) . ? Cl9 C83 1.745(3) . ? Cl3 C31 1.743(3) . ? Cl5 C50 1.743(3) . ? Cl1 C17 1.742(3) . ? Cl6 C57 1.750(4) . ? Cl8 C90 1.737(4) . ? O3 C28 1.380(3) . ? O3 C27 1.436(3) . ? O9 C80 1.379(3) . ? O9 C79 1.442(3) . ? O5 C47 1.378(3) . ? O5 C46 1.438(3) . ? O1 C14 1.370(4) . ? O1 C13 1.452(3) . ? O8 C87 1.373(4) . ? O8 C86 1.429(4) . ? C28 C29 1.374(4) . ? C28 C33 1.376(4) . ? C80 C85 1.373(4) . ? C80 C81 1.378(4) . ? O4 C61 1.379(4) . ? O4 C60 1.429(4) . ? O2 C21 1.381(3) . ? O2 C20 1.397(4) . ? C47 C48 1.377(4) . ? C47 C52 1.373(4) . ? O6 C54 1.365(4) . ? O6 C53 1.434(4) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C46 C34 1.511(4) . ? O7 C94 1.381(4) . ? O7 C93 1.420(4) . ? C79 H79A 0.9700 . ? C79 H79B 0.9700 . ? C79 C67 1.506(4) . ? C35 C34 1.391(4) . ? C35 C40 1.518(4) . ? C35 C36A 1.433(7) . ? C35 C36B 1.400(11) . ? C48 H48 0.9300 . ? C48 C49 1.397(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 C5 1.507(4) . ? C67 C68 1.394(4) . ? C67 C72 1.409(4) . ? C68 C73 1.515(4) . ? C68 C69B 1.440(8) . ? C68 C69A 1.367(18) . ? C14 C15 1.379(4) . ? C14 C19 1.370(4) . ? C61 C66 1.368(4) . ? C61 C62 1.382(4) . ? C5 C6 1.399(4) . ? C5 C4 1.402(4) . ? C87 C92 1.380(4) . ? C87 C88 1.378(5) . ? C29 H29 0.9300 . ? C29 C30 1.390(4) . ? C34 C39 1.405(4) . ? C6 C11 1.506(4) . ? C6 C1 1.400(4) . ? C66 H66 0.9300 . ? C66 C65 1.387(4) . ? C85 H85 0.9300 . ? C85 C84 1.383(4) . ? C21 C26 1.374(4) . ? C21 C22 1.379(4) . ? C54 C55 1.378(4) . ? C54 C59 1.374(4) . ? C95 H95 0.9300 . ? C95 C94 1.370(4) . ? C95 C96 1.385(4) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C40 C41 1.531(4) . ? C49 H49 0.9300 . ? C49 C50 1.359(4) . ? C91 H91 0.9300 . ? C91 C90 1.366(5) . ? C91 C92 1.362(5) . ? C94 C99 1.379(4) . ? C81 H81 0.9300 . ? C81 C82 1.380(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.526(4) . ? C26 H26 0.9300 . ? C26 C25 1.384(4) . ? C33 H33 0.9300 . ? C33 C32 1.374(4) . ? C96 H96 0.9300 . ? C96 C97 1.355(5) . ? C56 H56 0.9300 . ? C56 C57 1.378(5) . ? C56 C55 1.379(4) . ? C30 H30 0.9300 . ? C30 C31 1.360(4) . ? C72 C71B 1.459(7) . ? C72 C77 1.518(4) . ? C72 C71A 1.29(2) . ? C90 C89 1.364(5) . ? C25 H25 0.9300 . ? C25 C24 1.372(5) . ? C52 H52 0.9300 . ? C52 C51 1.374(4) . ? C73 H73A 0.9700 . ? C73 H73B 0.9700 . ? C73 C74 1.532(4) . ? C74 H74A 0.9600 . ? C74 H74B 0.9600 . ? C74 H74C 0.9600 . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C44 C39 1.517(4) . ? C44 C45 1.522(5) . ? C64 C65 1.366(5) . ? C64 C63 1.370(5) . ? C98 H98 0.9300 . ? C98 C99 1.368(4) . ? C98 C97 1.373(5) . ? C92 H92 0.9300 . ? C65 H65 0.9300 . ? C83 C84 1.361(4) . ? C83 C82 1.361(4) . ? C57 C58 1.358(5) . ? C55 H55 0.9300 . ? C50 C51 1.375(4) . ? C1 C13 1.514(4) . ? C1 C2 1.405(4) . ? C84 H84 0.9300 . ? C15 H15 0.9300 . ? C15 C16 1.373(4) . ? C88 H88 0.9300 . ? C88 C89 1.366(5) . ? C32 H32 0.9300 . ? C32 C31 1.369(4) . ? C17 C18 1.369(5) . ? C17 C16 1.367(5) . ? C63 H63 0.9300 . ? C63 C62 1.380(5) . ? C99 H99 0.9300 . ? C24 C23 1.369(4) . ? C59 H59 0.9300 . ? C59 C58 1.372(5) . ? C69B C70B 1.415(8) . ? C69B C86 1.472(7) . ? C19 H19 0.9300 . ? C19 C18 1.381(5) . ? C36A C37A 1.407(9) . ? C36A C53 1.503(7) . ? C22 H22 0.9300 . ? C22 C23 1.385(4) . ? C39 C38A 1.452(8) . ? C39 C38B 1.372(13) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C4 1.516(4) . ? C9 C10 1.527(4) . ? C71B C70B 1.395(7) . ? C71B C93 1.500(6) . ? C3 C20 1.516(4) . ? C3 C4 1.397(4) . ? C3 C2 1.414(4) . ? C62 H62 0.9300 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C82 H82 0.9300 . ? C89 H89 0.9300 . ? C23 H23 0.9300 . ? C58 H58 0.9300 . ? C18 H18 0.9300 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C16 H16 0.9300 . ? C37A C38A 1.400(9) . ? C37A C42A 1.527(13) . ? C51 H51 0.9300 . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C53 H53C 0.9700 . ? C53 H53D 0.9700 . ? C53 C36B 1.560(11) . ? C70B C75B 1.517(9) . ? C77 H77A 0.9700 . ? C77 H77B 0.9700 . ? C77 C78 1.517(5) . ? C86 H86A 0.9700 . ? C86 H86B 0.9700 . ? C86 H86C 0.9700 . ? C86 H86D 0.9700 . ? C86 C69A 1.641(19) . ? C38A C60 1.496(7) . ? C78 H78A 0.9600 . ? C78 H78B 0.9600 . ? C78 H78C 0.9600 . ? C93 H93A 0.9700 . ? C93 H93B 0.9700 . ? C93 H93C 0.9700 . ? C93 H93D 0.9700 . ? C93 C71A 1.68(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C8 C7 1.510(4) . ? C2 C7 1.513(4) . ? C75B H75A 0.9700 . ? C75B H75B 0.9700 . ? C75B C76B 1.507(10) . ? C60 H60A 0.9700 . ? C60 H60B 0.9700 . ? C60 H60C 0.9700 . ? C60 H60D 0.9700 . ? C60 C38B 1.611(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C43A H43A 0.9600 . ? C43A H43B 0.9600 . ? C43A H43C 0.9600 . ? C43A C42A 1.540(14) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C76B H76A 0.9600 . ? C76B H76B 0.9600 . ? C76B H76C 0.9600 . ? C42A H42A 0.9700 . ? C42A H42B 0.9700 . ? C75A H75C 0.9700 . ? C75A H75D 0.9700 . ? C75A C70A 1.50(2) . ? C75A C76A 1.57(3) . ? C37B C42B 1.489(19) . ? C37B C36B 1.383(15) . ? C37B C38B 1.412(17) . ? C42B H42C 0.9700 . ? C42B H42D 0.9700 . ? C42B C43B 1.52(3) . ? C70A C71A 1.42(2) . ? C70A C69A 1.38(2) . ? C76A H76D 0.9600 . ? C76A H76E 0.9600 . ? C76A H76F 0.9600 . ? C43B H43D 0.9600 . ? C43B H43E 0.9600 . ? C43B H43F 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 C28 O3 C27 117.3(2) . . ? C80 O9 C79 118.5(2) . . ? C47 O5 C46 119.4(2) . . ? C14 O1 C13 117.2(2) . . ? C87 O8 C86 117.2(3) . . ? C29 C28 O3 124.4(3) . . ? C29 C28 C33 119.8(3) . . ? C33 C28 O3 115.8(3) . . ? C85 C80 O9 124.8(3) . . ? C85 C80 C81 120.1(3) . . ? C81 C80 O9 115.1(3) . . ? C61 O4 C60 116.7(3) . . ? C21 O2 C20 117.7(2) . . ? C48 C47 O5 124.2(3) . . ? C52 C47 O5 115.6(3) . . ? C52 C47 C48 120.2(3) . . ? C54 O6 C53 117.3(3) . . ? O5 C46 H46A 110.8 . . ? O5 C46 H46B 110.8 . . ? O5 C46 C34 104.6(2) . . ? H46A C46 H46B 108.9 . . ? C34 C46 H46A 110.8 . . ? C34 C46 H46B 110.8 . . ? C94 O7 C93 115.8(3) . . ? O9 C79 H79A 110.7 . . ? O9 C79 H79B 110.7 . . ? O9 C79 C67 105.2(2) . . ? H79A C79 H79B 108.8 . . ? C67 C79 H79A 110.7 . . ? C67 C79 H79B 110.7 . . ? C34 C35 C40 120.6(3) . . ? C34 C35 C36A 119.9(4) . . ? C34 C35 C36B 118.6(5) . . ? C36A C35 C40 118.8(4) . . ? C36B C35 C40 119.4(5) . . ? C36B C35 C36A 20.6(4) . . ? C47 C48 H48 120.6 . . ? C47 C48 C49 118.8(3) . . ? C49 C48 H48 120.6 . . ? O3 C27 H27A 110.3 . . ? O3 C27 H27B 110.3 . . ? O3 C27 C5 107.0(2) . . ? H27A C27 H27B 108.6 . . ? C5 C27 H27A 110.3 . . ? C5 C27 H27B 110.3 . . ? C68 C67 C79 119.0(3) . . ? C68 C67 C72 120.8(3) . . ? C72 C67 C79 119.9(3) . . ? C67 C68 C73 121.1(3) . . ? C67 C68 C69B 120.3(4) . . ? C69B C68 C73 118.4(4) . . ? C69A C68 C67 115.2(8) . . ? C69A C68 C73 121.6(9) . . ? C69A C68 C69B 19.4(7) . . ? O1 C14 C15 124.6(3) . . ? O1 C14 C19 116.6(3) . . ? C19 C14 C15 118.8(3) . . ? O4 C61 C62 115.5(3) . . ? C66 C61 O4 124.9(3) . . ? C66 C61 C62 119.6(3) . . ? C6 C5 C27 119.3(2) . . ? C6 C5 C4 121.1(2) . . ? C4 C5 C27 119.5(3) . . ? O8 C87 C92 124.5(3) . . ? O8 C87 C88 116.4(3) . . ? C88 C87 C92 119.1(3) . . ? C28 C29 H29 120.3 . . ? C28 C29 C30 119.3(3) . . ? C30 C29 H29 120.3 . . ? C35 C34 C46 119.5(3) . . ? C35 C34 C39 120.7(3) . . ? C39 C34 C46 119.6(3) . . ? C5 C6 C11 120.7(2) . . ? C5 C6 C1 118.9(3) . . ? C1 C6 C11 120.3(3) . . ? C61 C66 H66 119.9 . . ? C61 C66 C65 120.2(3) . . ? C65 C66 H66 119.9 . . ? C80 C85 H85 120.4 . . ? C80 C85 C84 119.1(3) . . ? C84 C85 H85 120.4 . . ? C26 C21 O2 114.6(3) . . ? C26 C21 C22 120.1(3) . . ? C22 C21 O2 125.3(3) . . ? O6 C54 C55 124.4(3) . . ? O6 C54 C59 115.3(3) . . ? C59 C54 C55 120.3(3) . . ? C94 C95 H95 119.9 . . ? C94 C95 C96 120.1(3) . . ? C96 C95 H95 119.9 . . ? C35 C40 H40A 109.0 . . ? C35 C40 H40B 109.0 . . ? C35 C40 C41 112.8(3) . . ? H40A C40 H40B 107.8 . . ? C41 C40 H40A 109.0 . . ? C41 C40 H40B 109.0 . . ? C48 C49 H49 119.8 . . ? C50 C49 C48 120.4(3) . . ? C50 C49 H49 119.8 . . ? C90 C91 H91 120.0 . . ? C92 C91 H91 120.0 . . ? C92 C91 C90 120.0(4) . . ? C95 C94 O7 124.8(3) . . ? C95 C94 C99 118.9(3) . . ? C99 C94 O7 116.3(3) . . ? C80 C81 H81 120.0 . . ? C80 C81 C82 120.0(3) . . ? C82 C81 H81 120.0 . . ? C6 C11 H11A 109.4 . . ? C6 C11 H11B 109.4 . . ? C6 C11 C12 111.0(3) . . ? H11A C11 H11B 108.0 . . ? C12 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? C21 C26 H26 120.2 . . ? C21 C26 C25 119.7(3) . . ? C25 C26 H26 120.2 . . ? C28 C33 H33 119.8 . . ? C32 C33 C28 120.5(3) . . ? C32 C33 H33 119.8 . . ? C95 C96 H96 119.8 . . ? C97 C96 C95 120.3(4) . . ? C97 C96 H96 119.8 . . ? C57 C56 H56 120.4 . . ? C57 C56 C55 119.2(3) . . ? C55 C56 H56 120.4 . . ? C29 C30 H30 119.9 . . ? C31 C30 C29 120.3(3) . . ? C31 C30 H30 119.9 . . ? C67 C72 C71B 118.2(3) . . ? C67 C72 C77 120.1(3) . . ? C71B C72 C77 121.6(3) . . ? C71A C72 C67 119.6(10) . . ? C71A C72 C71B 21.3(9) . . ? C71A C72 C77 116.4(10) . . ? C91 C90 Cl8 119.5(3) . . ? C89 C90 Cl8 120.2(3) . . ? C89 C90 C91 120.3(4) . . ? C26 C25 H25 119.9 . . ? C24 C25 C26 120.3(3) . . ? C24 C25 H25 119.9 . . ? C47 C52 H52 119.7 . . ? C47 C52 C51 120.6(3) . . ? C51 C52 H52 119.7 . . ? C68 C73 H73A 109.0 . . ? C68 C73 H73B 109.0 . . ? C68 C73 C74 112.9(3) . . ? H73A C73 H73B 107.8 . . ? C74 C73 H73A 109.0 . . ? C74 C73 H73B 109.0 . . ? C73 C74 H74A 109.5 . . ? C73 C74 H74B 109.5 . . ? C73 C74 H74C 109.5 . . ? H74A C74 H74B 109.5 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? H44A C44 H44B 107.9 . . ? C39 C44 H44A 109.2 . . ? C39 C44 H44B 109.2 . . ? C39 C44 C45 111.9(3) . . ? C45 C44 H44A 109.2 . . ? C45 C44 H44B 109.2 . . ? C65 C64 Cl4 119.9(3) . . ? C65 C64 C63 120.7(3) . . ? C63 C64 Cl4 119.4(3) . . ? C99 C98 H98 120.1 . . ? C99 C98 C97 119.8(3) . . ? C97 C98 H98 120.1 . . ? C87 C92 H92 119.8 . . ? C91 C92 C87 120.4(3) . . ? C91 C92 H92 119.8 . . ? C66 C65 H65 120.2 . . ? C64 C65 C66 119.7(4) . . ? C64 C65 H65 120.2 . . ? C84 C83 Cl9 120.0(3) . . ? C82 C83 Cl9 119.3(3) . . ? C82 C83 C84 120.7(3) . . ? C56 C57 Cl6 118.5(3) . . ? C58 C57 Cl6 120.7(3) . . ? C58 C57 C56 120.9(3) . . ? C54 C55 C56 119.8(3) . . ? C54 C55 H55 120.1 . . ? C56 C55 H55 120.1 . . ? C49 C50 Cl5 121.0(3) . . ? C49 C50 C51 120.5(3) . . ? C51 C50 Cl5 118.5(3) . . ? C6 C1 C13 118.2(3) . . ? C6 C1 C2 121.0(3) . . ? C2 C1 C13 120.8(3) . . ? C85 C84 H84 119.8 . . ? C83 C84 C85 120.5(3) . . ? C83 C84 H84 119.8 . . ? C14 C15 H15 119.8 . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.8 . . ? C87 C88 H88 120.0 . . ? C89 C88 C87 120.1(3) . . ? C89 C88 H88 120.0 . . ? C33 C32 H32 120.2 . . ? C31 C32 C33 119.6(3) . . ? C31 C32 H32 120.2 . . ? C18 C17 Cl1 120.4(3) . . ? C16 C17 Cl1 119.7(3) . . ? C16 C17 C18 120.0(3) . . ? C64 C63 H63 120.2 . . ? C64 C63 C62 119.6(4) . . ? C62 C63 H63 120.2 . . ? C30 C31 Cl3 119.5(3) . . ? C30 C31 C32 120.5(3) . . ? C32 C31 Cl3 120.0(3) . . ? C94 C99 H99 119.6 . . ? C98 C99 C94 120.8(3) . . ? C98 C99 H99 119.6 . . ? C25 C24 Cl2 119.6(3) . . ? C23 C24 Cl2 120.3(3) . . ? C23 C24 C25 120.1(3) . . ? C54 C59 H59 120.2 . . ? C58 C59 C54 119.6(3) . . ? C58 C59 H59 120.2 . . ? C68 C69B C86 119.6(5) . . ? C70B C69B C68 119.7(5) . . ? C70B C69B C86 120.6(6) . . ? C14 C19 H19 119.5 . . ? C14 C19 C18 121.1(3) . . ? C18 C19 H19 119.5 . . ? C35 C36A C53 118.1(5) . . ? C37A C36A C35 120.0(5) . . ? C37A C36A C53 120.7(6) . . ? C21 C22 H22 120.1 . . ? C21 C22 C23 119.7(3) . . ? C23 C22 H22 120.1 . . ? C34 C39 C44 120.3(3) . . ? C34 C39 C38A 118.7(4) . . ? C38A C39 C44 120.9(4) . . ? C38B C39 C34 118.5(6) . . ? C38B C39 C44 118.8(6) . . ? C38B C39 C38A 19.1(5) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H9A C9 H9B 107.8 . . ? C4 C9 H9A 109.1 . . ? C4 C9 H9B 109.1 . . ? C4 C9 C10 112.6(3) . . ? C10 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C96 C97 Cl7 120.1(3) . . ? C96 C97 C98 120.0(3) . . ? C98 C97 Cl7 119.9(3) . . ? C72 C71B C93 118.2(4) . . ? C70B C71B C72 121.0(4) . . ? C70B C71B C93 120.8(5) . . ? C4 C3 C20 120.2(3) . . ? C4 C3 C2 120.2(3) . . ? C2 C3 C20 119.6(3) . . ? C61 C62 H62 119.9 . . ? C63 C62 C61 120.2(3) . . ? C63 C62 H62 119.9 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41B 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O1 C13 C1 107.6(2) . . ? O1 C13 H13A 110.2 . . ? O1 C13 H13B 110.2 . . ? C1 C13 H13A 110.2 . . ? C1 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? C81 C82 H82 120.2 . . ? C83 C82 C81 119.6(3) . . ? C83 C82 H82 120.2 . . ? C90 C89 C88 120.1(3) . . ? C90 C89 H89 119.9 . . ? C88 C89 H89 119.9 . . ? C24 C23 C22 120.1(3) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C57 C58 C59 120.2(3) . . ? C57 C58 H58 119.9 . . ? C59 C58 H58 119.9 . . ? C17 C18 C19 119.4(3) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45B 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O2 C20 C3 108.3(3) . . ? O2 C20 H20A 110.0 . . ? O2 C20 H20B 110.0 . . ? C3 C20 H20A 110.0 . . ? C3 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? C15 C16 H16 119.8 . . ? C17 C16 C15 120.4(3) . . ? C17 C16 H16 119.8 . . ? C36A C37A C42A 119.4(6) . . ? C38A C37A C36A 119.9(6) . . ? C38A C37A C42A 120.7(6) . . ? C52 C51 C50 119.5(3) . . ? C52 C51 H51 120.3 . . ? C50 C51 H51 120.3 . . ? O6 C53 C36A 101.2(4) . . ? O6 C53 H53A 111.5 . . ? O6 C53 H53B 111.5 . . ? O6 C53 H53C 107.3 . . ? O6 C53 H53D 107.3 . . ? O6 C53 C36B 119.9(5) . . ? C36A C53 H53A 111.5 . . ? C36A C53 H53B 111.5 . . ? C36A C53 H53C 114.1 . . ? C36A C53 H53D 119.0 . . ? C36A C53 C36B 18.9(4) . . ? H53A C53 H53B 109.3 . . ? H53A C53 H53C 4.3 . . ? H53A C53 H53D 106.1 . . ? H53B C53 H53C 110.7 . . ? H53B C53 H53D 7.6 . . ? H53C C53 H53D 106.9 . . ? C36B C53 H53A 103.8 . . ? C36B C53 H53B 99.8 . . ? C36B C53 H53C 107.3 . . ? C36B C53 H53D 107.3 . . ? C5 C4 C9 120.0(3) . . ? C3 C4 C5 119.5(3) . . ? C3 C4 C9 120.4(3) . . ? C69B C70B C75B 119.7(5) . . ? C71B C70B C69B 119.6(5) . . ? C71B C70B C75B 120.7(4) . . ? C72 C77 H77A 109.2 . . ? C72 C77 H77B 109.2 . . ? H77A C77 H77B 107.9 . . ? C78 C77 C72 112.1(3) . . ? C78 C77 H77A 109.2 . . ? C78 C77 H77B 109.2 . . ? O8 C86 C69B 103.9(4) . . ? O8 C86 H86A 111.0 . . ? O8 C86 H86B 111.0 . . ? O8 C86 H86C 107.3 . . ? O8 C86 H86D 107.3 . . ? O8 C86 C69A 120.0(6) . . ? C69B C86 H86A 111.0 . . ? C69B C86 H86B 111.0 . . ? C69B C86 H86C 118.8 . . ? C69B C86 H86D 112.0 . . ? C69B C86 C69A 16.5(6) . . ? H86A C86 H86B 109.0 . . ? H86A C86 H86C 7.8 . . ? H86A C86 H86D 111.4 . . ? H86B C86 H86C 104.8 . . ? H86B C86 H86D 3.7 . . ? H86C C86 H86D 106.9 . . ? C69A C86 H86A 99.6 . . ? C69A C86 H86B 105.4 . . ? C69A C86 H86C 107.3 . . ? C69A C86 H86D 107.3 . . ? C39 C38A C60 118.8(5) . . ? C37A C38A C39 120.1(5) . . ? C37A C38A C60 120.8(6) . . ? C77 C78 H78A 109.5 . . ? C77 C78 H78B 109.5 . . ? C77 C78 H78C 109.5 . . ? H78A C78 H78B 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? O7 C93 C71B 112.8(4) . . ? O7 C93 H93A 109.0 . . ? O7 C93 H93B 109.0 . . ? O7 C93 H93C 112.8 . . ? O7 C93 H93D 112.8 . . ? O7 C93 C71A 94.7(7) . . ? C71B C93 H93A 109.0 . . ? C71B C93 H93B 109.0 . . ? C71B C93 H93C 106.0 . . ? C71B C93 H93D 101.5 . . ? C71B C93 C71A 18.3(7) . . ? H93A C93 H93B 107.8 . . ? H93A C93 H93C 3.9 . . ? H93A C93 H93D 111.6 . . ? H93B C93 H93C 107.0 . . ? H93B C93 H93D 7.6 . . ? H93C C93 H93D 110.2 . . ? C71A C93 H93A 114.9 . . ? C71A C93 H93B 120.2 . . ? C71A C93 H93C 112.8 . . ? C71A C93 H93D 112.8 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? C1 C2 C3 119.1(2) . . ? C1 C2 C7 120.6(3) . . ? C3 C2 C7 120.3(3) . . ? C70B C75B H75A 109.4 . . ? C70B C75B H75B 109.4 . . ? H75A C75B H75B 108.0 . . ? C76B C75B C70B 111.1(7) . . ? C76B C75B H75A 109.4 . . ? C76B C75B H75B 109.4 . . ? O4 C60 C38A 113.8(4) . . ? O4 C60 H60A 108.8 . . ? O4 C60 H60B 108.8 . . ? O4 C60 H60C 112.4 . . ? O4 C60 H60D 112.4 . . ? O4 C60 C38B 96.8(5) . . ? C38A C60 H60A 108.8 . . ? C38A C60 H60B 108.8 . . ? C38A C60 H60C 105.5 . . ? C38A C60 H60D 102.1 . . ? C38A C60 C38B 17.1(5) . . ? H60A C60 H60B 107.7 . . ? H60A C60 H60C 3.9 . . ? H60A C60 H60D 110.8 . . ? H60B C60 H60C 107.3 . . ? H60B C60 H60D 6.7 . . ? H60C C60 H60D 110.0 . . ? C38B C60 H60A 114.9 . . ? C38B C60 H60B 118.9 . . ? C38B C60 H60C 112.4 . . ? C38B C60 H60D 112.4 . . ? C8 C7 C2 112.8(3) . . ? C8 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C2 C7 H7A 109.0 . . ? C2 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C37A C42A C43A 110.4(11) . . ? C37A C42A H42A 109.6 . . ? C37A C42A H42B 109.6 . . ? C43A C42A H42A 109.6 . . ? C43A C42A H42B 109.6 . . ? H42A C42A H42B 108.1 . . ? H75C C75A H75D 107.5 . . ? C70A C75A H75C 108.5 . . ? C70A C75A H75D 108.5 . . ? C70A C75A C76A 115.2(17) . . ? C76A C75A H75C 108.5 . . ? C76A C75A H75D 108.5 . . ? C36B C37B C42B 120.9(10) . . ? C36B C37B C38B 119.4(10) . . ? C38B C37B C42B 119.7(10) . . ? C37B C42B H42C 108.0 . . ? C37B C42B H42D 108.0 . . ? C37B C42B C43B 117(2) . . ? H42C C42B H42D 107.3 . . ? C43B C42B H42C 108.0 . . ? C43B C42B H42D 108.0 . . ? C71A C70A C75A 121.9(14) . . ? C69A C70A C75A 120.6(13) . . ? C69A C70A C71A 117.4(15) . . ? C42B C43B H43D 109.5 . . ? C42B C43B H43E 109.5 . . ? C42B C43B H43F 109.5 . . ? H43D C43B H43E 109.5 . . ? H43D C43B H43F 109.5 . . ? H43E C43B H43F 109.5 . . ? C35 C36B C53 116.5(7) . . ? C37B C36B C35 120.3(9) . . ? C37B C36B C53 119.4(8) . . ? C39 C38B C60 116.4(9) . . ? C39 C38B C37B 121.0(11) . . ? C37B C38B C60 118.8(10) . . ? C72 C71A C93 117.3(15) . . ? C72 C71A C70A 121.3(17) . . ? C70A C71A C93 112.7(14) . . ? C68 C69A C86 113.2(12) . . ? C68 C69A C70A 123.3(15) . . ? C70A C69A C86 119.6(13) . . ? 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 Cl4 C64 C65 C66 -178.3(3) . . . . ? Cl4 C64 C63 C62 178.8(3) . . . . ? Cl2 C24 C23 C22 177.6(2) . . . . ? Cl9 C83 C84 C85 179.9(2) . . . . ? Cl9 C83 C82 C81 -179.7(3) . . . . ? Cl5 C50 C51 C52 179.6(3) . . . . ? Cl1 C17 C18 C19 -179.4(3) . . . . ? Cl1 C17 C16 C15 179.8(3) . . . . ? Cl6 C57 C58 C59 179.7(3) . . . . ? Cl8 C90 C89 C88 -179.9(3) . . . . ? O3 C28 C29 C30 -179.9(3) . . . . ? O3 C28 C33 C32 179.7(3) . . . . ? O3 C27 C5 C6 -83.0(3) . . . . ? O3 C27 C5 C4 97.1(3) . . . . ? O9 C80 C85 C84 179.6(3) . . . . ? O9 C80 C81 C82 -179.5(3) . . . . ? O9 C79 C67 C68 84.0(3) . . . . ? O9 C79 C67 C72 -90.2(3) . . . . ? O5 C47 C48 C49 -179.3(3) . . . . ? O5 C47 C52 C51 179.1(3) . . . . ? O5 C46 C34 C35 -84.6(3) . . . . ? O5 C46 C34 C39 89.7(3) . . . . ? O1 C14 C15 C16 179.9(3) . . . . ? O1 C14 C19 C18 -179.4(3) . . . . ? O8 C87 C92 C91 179.8(4) . . . . ? O8 C87 C88 C89 179.8(3) . . . . ? O8 C86 C69A C68 -61.4(13) . . . . ? O8 C86 C69A C70A 97.1(12) . . . . ? C28 O3 C27 C5 179.8(2) . . . . ? C28 C29 C30 C31 0.5(5) . . . . ? C28 C33 C32 C31 -0.1(5) . . . . ? C80 O9 C79 C67 -175.4(2) . . . . ? C80 C85 C84 C83 -0.5(5) . . . . ? C80 C81 C82 C83 0.3(5) . . . . ? O4 C61 C66 C65 -178.8(3) . . . . ? O4 C61 C62 C63 179.5(3) . . . . ? O4 C60 C38B C39 95.0(9) . . . . ? O4 C60 C38B C37B -107.0(9) . . . . ? O2 C21 C26 C25 177.8(3) . . . . ? O2 C21 C22 C23 -177.2(3) . . . . ? C47 O5 C46 C34 174.8(3) . . . . ? C47 C48 C49 C50 0.3(5) . . . . ? C47 C52 C51 C50 0.1(5) . . . . ? O6 C54 C55 C56 179.3(3) . . . . ? O6 C54 C59 C58 -178.7(3) . . . . ? O6 C53 C36B C35 65.6(10) . . . . ? O6 C53 C36B C37B -92.4(9) . . . . ? C46 O5 C47 C48 3.5(4) . . . . ? C46 O5 C47 C52 -175.9(3) . . . . ? C46 C34 C39 C44 11.4(4) . . . . ? C46 C34 C39 C38A -164.4(5) . . . . ? C46 C34 C39 C38B 173.8(7) . . . . ? O7 C94 C99 C98 -179.7(3) . . . . ? O7 C93 C71A C72 -104.6(14) . . . . ? O7 C93 C71A C70A 107.4(12) . . . . ? C79 O9 C80 C85 -1.8(4) . . . . ? C79 O9 C80 C81 177.9(3) . . . . ? C79 C67 C68 C73 4.4(4) . . . . ? C79 C67 C68 C69B -170.4(4) . . . . ? C79 C67 C68 C69A 168.4(8) . . . . ? C79 C67 C72 C71B 167.6(4) . . . . ? C79 C67 C72 C77 -11.2(4) . . . . ? C79 C67 C72 C71A -168.2(11) . . . . ? C35 C34 C39 C44 -174.3(3) . . . . ? C35 C34 C39 C38A 9.9(6) . . . . ? C35 C34 C39 C38B -11.9(8) . . . . ? C35 C36A C37A C38A 0.7(9) . . . . ? C35 C36A C37A C42A -177.0(8) . . . . ? C35 C36A C53 O6 100.1(7) . . . . ? C35 C36A C53 C36B -72.5(18) . . . . ? C48 C47 C52 C51 -0.3(5) . . . . ? C48 C49 C50 Cl5 -179.8(2) . . . . ? C48 C49 C50 C51 -0.5(5) . . . . ? C27 O3 C28 C29 4.3(4) . . . . ? C27 O3 C28 C33 -176.0(3) . . . . ? C27 C5 C6 C11 -5.4(4) . . . . ? C27 C5 C6 C1 178.7(3) . . . . ? C27 C5 C4 C9 -0.4(4) . . . . ? C27 C5 C4 C3 176.9(3) . . . . ? C67 C68 C73 C74 89.9(4) . . . . ? C67 C68 C69B C70B 1.7(8) . . . . ? C67 C68 C69B C86 -174.0(4) . . . . ? C67 C68 C69A C86 167.8(7) . . . . ? C67 C68 C69A C70A 10.2(15) . . . . ? C67 C72 C71B C70B 4.1(7) . . . . ? C67 C72 C71B C93 -174.8(4) . . . . ? C67 C72 C77 C78 -80.8(4) . . . . ? C67 C72 C71A C93 -154.6(9) . . . . ? C67 C72 C71A C70A -9.5(19) . . . . ? C68 C67 C72 C71B -6.5(5) . . . . ? C68 C67 C72 C77 174.6(3) . . . . ? C68 C67 C72 C71A 17.7(11) . . . . ? C68 C69B C70B C71B -4.1(9) . . . . ? C68 C69B C70B C75B 176.9(6) . . . . ? C68 C69B C86 O8 -92.2(6) . . . . ? C68 C69B C86 C69A 76(3) . . . . ? C14 O1 C13 C1 -166.7(2) . . . . ? C14 C15 C16 C17 0.0(6) . . . . ? C14 C19 C18 C17 -1.0(5) . . . . ? C61 O4 C60 C38A 179.6(4) . . . . ? C61 O4 C60 C38B 177.5(5) . . . . ? C61 C66 C65 C64 -0.1(5) . . . . ? C5 C6 C11 C12 -89.3(3) . . . . ? C5 C6 C1 C13 -177.6(3) . . . . ? C5 C6 C1 C2 3.4(4) . . . . ? C87 O8 C86 C69B 173.2(4) . . . . ? C87 O8 C86 C69A 169.2(8) . . . . ? C87 C88 C89 C90 0.9(6) . . . . ? C29 C28 C33 C32 -0.6(5) . . . . ? C29 C30 C31 Cl3 179.1(2) . . . . ? C29 C30 C31 C32 -1.2(5) . . . . ? C34 C35 C40 C41 -90.9(4) . . . . ? C34 C35 C36A C37A 2.6(8) . . . . ? C34 C35 C36A C53 170.9(5) . . . . ? C34 C35 C36B C53 -168.1(5) . . . . ? C34 C35 C36B C37B -10.3(10) . . . . ? C34 C39 C38A C37A -6.5(8) . . . . ? C34 C39 C38A C60 179.7(5) . . . . ? C34 C39 C38B C60 160.6(6) . . . . ? C34 C39 C38B C37B 3.0(12) . . . . ? C6 C5 C4 C9 179.7(3) . . . . ? C6 C5 C4 C3 -3.0(4) . . . . ? C6 C1 C13 O1 73.6(3) . . . . ? C6 C1 C2 C3 -1.1(4) . . . . ? C6 C1 C2 C7 179.8(3) . . . . ? C66 C61 C62 C63 1.3(5) . . . . ? C85 C80 C81 C82 0.2(5) . . . . ? C21 O2 C20 C3 177.3(2) . . . . ? C21 C26 C25 C24 -0.4(5) . . . . ? C21 C22 C23 C24 -0.8(5) . . . . ? C54 O6 C53 C36A -177.2(4) . . . . ? C54 O6 C53 C36B -174.5(5) . . . . ? C54 C59 C58 C57 -1.0(5) . . . . ? C95 C94 C99 C98 0.1(5) . . . . ? C95 C96 C97 Cl7 177.5(3) . . . . ? C95 C96 C97 C98 -0.2(6) . . . . ? C40 C35 C34 C46 -4.1(4) . . . . ? C40 C35 C34 C39 -178.4(3) . . . . ? C40 C35 C36A C37A 173.1(4) . . . . ? C40 C35 C36A C53 -18.6(9) . . . . ? C40 C35 C36B C53 25.6(11) . . . . ? C40 C35 C36B C37B -176.6(8) . . . . ? C49 C50 C51 C52 0.3(5) . . . . ? C91 C90 C89 C88 -1.4(6) . . . . ? C94 O7 C93 C71B 178.1(3) . . . . ? C94 O7 C93 C71A 175.1(8) . . . . ? C94 C95 C96 C97 0.6(5) . . . . ? C81 C80 C85 C84 -0.1(5) . . . . ? C11 C6 C1 C13 6.5(4) . . . . ? C11 C6 C1 C2 -172.5(3) . . . . ? C26 C21 C22 C23 2.5(4) . . . . ? C26 C25 C24 Cl2 -177.0(2) . . . . ? C26 C25 C24 C23 2.2(5) . . . . ? C33 C28 C29 C30 0.4(5) . . . . ? C33 C32 C31 Cl3 -179.3(3) . . . . ? C33 C32 C31 C30 1.0(5) . . . . ? C96 C95 C94 O7 179.3(3) . . . . ? C96 C95 C94 C99 -0.5(5) . . . . ? C56 C57 C58 C59 0.7(5) . . . . ? C72 C67 C68 C73 178.6(3) . . . . ? C72 C67 C68 C69B 3.8(6) . . . . ? C72 C67 C68 C69A -17.4(9) . . . . ? C72 C71B C70B C69B 1.2(9) . . . . ? C72 C71B C70B C75B -179.8(5) . . . . ? C72 C71B C93 O7 -71.6(6) . . . . ? C72 C71B C93 C71A -62(3) . . . . ? C90 C91 C92 C87 0.0(6) . . . . ? C25 C24 C23 C22 -1.6(5) . . . . ? C52 C47 C48 C49 0.0(5) . . . . ? C73 C68 C69B C70B -173.3(4) . . . . ? C73 C68 C69B C86 11.1(8) . . . . ? C73 C68 C69A C86 -28.3(13) . . . . ? C73 C68 C69A C70A 174.1(10) . . . . ? C44 C39 C38A C37A 177.7(5) . . . . ? C44 C39 C38A C60 4.0(9) . . . . ? C44 C39 C38B C60 -36.7(12) . . . . ? C44 C39 C38B C37B 165.7(8) . . . . ? C64 C63 C62 C61 -0.9(5) . . . . ? C92 C87 C88 C89 0.0(5) . . . . ? C92 C91 C90 Cl8 179.4(3) . . . . ? C92 C91 C90 C89 0.9(6) . . . . ? C65 C64 C63 C62 -0.1(6) . . . . ? C57 C56 C55 C54 -0.3(5) . . . . ? C55 C54 C59 C58 0.6(5) . . . . ? C55 C56 C57 Cl6 -179.1(3) . . . . ? C55 C56 C57 C58 -0.1(5) . . . . ? C1 C6 C11 C12 86.6(4) . . . . ? C1 C2 C7 C8 77.2(4) . . . . ? C84 C83 C82 C81 -0.9(5) . . . . ? C15 C14 C19 C18 0.0(5) . . . . ? C88 C87 C92 C91 -0.4(6) . . . . ? C63 C64 C65 C66 0.6(6) . . . . ? C99 C98 C97 Cl7 -177.9(3) . . . . ? C99 C98 C97 C96 -0.2(5) . . . . ? C59 C54 C55 C56 0.0(5) . . . . ? C69B C68 C73 C74 -95.2(5) . . . . ? C69B C68 C69A C86 58(3) . . . . ? C69B C68 C69A C70A -100(3) . . . . ? C69B C70B C75B C76B 99.7(6) . . . . ? C69B C86 C69A C68 -75(3) . . . . ? C69B C86 C69A C70A 83(3) . . . . ? C19 C14 C15 C16 0.5(5) . . . . ? C36A C35 C34 C46 166.3(5) . . . . ? C36A C35 C34 C39 -8.1(6) . . . . ? C36A C35 C40 C41 98.7(5) . . . . ? C36A C35 C36B C53 -68.5(17) . . . . ? C36A C35 C36B C37B 89.3(19) . . . . ? C36A C37A C38A C39 1.3(9) . . . . ? C36A C37A C38A C60 174.9(6) . . . . ? C36A C37A C42A C43A -100.8(7) . . . . ? C36A C53 C36B C35 74.0(18) . . . . ? C36A C53 C36B C37B -84.0(19) . . . . ? C22 C21 C26 C25 -2.0(5) . . . . ? C39 C38A C60 O4 63.6(7) . . . . ? C39 C38A C60 C38B 71(2) . . . . ? C97 C98 C99 C94 0.3(5) . . . . ? C71B C72 C77 C78 100.5(5) . . . . ? C71B C72 C71A C93 -62(3) . . . . ? C71B C72 C71A C70A 83(3) . . . . ? C71B C70B C75B C76B -79.3(7) . . . . ? C71B C93 C71A C72 84(3) . . . . ? C71B C93 C71A C70A -64(3) . . . . ? C3 C2 C7 C8 -101.9(3) . . . . ? C62 C61 C66 C65 -0.8(5) . . . . ? C13 O1 C14 C15 -12.0(4) . . . . ? C13 O1 C14 C19 167.4(3) . . . . ? C13 C1 C2 C3 180.0(3) . . . . ? C13 C1 C2 C7 0.9(4) . . . . ? C82 C83 C84 C85 1.0(5) . . . . ? C18 C17 C16 C15 -1.0(6) . . . . ? C45 C44 C39 C34 78.3(4) . . . . ? C45 C44 C39 C38A -106.1(5) . . . . ? C45 C44 C39 C38B -84.1(8) . . . . ? C20 O2 C21 C26 175.3(3) . . . . ? C20 O2 C21 C22 -5.0(4) . . . . ? C20 C3 C4 C5 -172.8(3) . . . . ? C20 C3 C4 C9 4.5(4) . . . . ? C20 C3 C2 C1 174.8(3) . . . . ? C20 C3 C2 C7 -6.1(4) . . . . ? C16 C17 C18 C19 1.5(5) . . . . ? C37A C36A C53 O6 -91.7(6) . . . . ? C37A C36A C53 C36B 95.7(19) . . . . ? C37A C38A C60 O4 -110.0(6) . . . . ? C37A C38A C60 C38B -103(3) . . . . ? C53 O6 C54 C55 -8.5(5) . . . . ? C53 O6 C54 C59 170.8(3) . . . . ? C53 C36A C37A C38A -167.3(7) . . . . ? C53 C36A C37A C42A 15.0(9) . . . . ? C4 C5 C6 C11 174.5(3) . . . . ? C4 C5 C6 C1 -1.4(4) . . . . ? C4 C3 C20 O2 -111.3(3) . . . . ? C4 C3 C2 C1 -3.3(4) . . . . ? C4 C3 C2 C7 175.8(3) . . . . ? C70B C69B C86 O8 92.2(6) . . . . ? C70B C69B C86 C69A -100(3) . . . . ? C70B C71B C93 O7 109.5(6) . . . . ? C70B C71B C93 C71A 119(3) . . . . ? C77 C72 C71B C70B -177.1(4) . . . . ? C77 C72 C71B C93 4.0(7) . . . . ? C77 C72 C71A C93 47.6(16) . . . . ? C77 C72 C71A C70A -167.3(11) . . . . ? C86 O8 C87 C92 13.9(5) . . . . ? C86 O8 C87 C88 -166.0(3) . . . . ? C86 C69B C70B C71B 171.5(6) . . . . ? C86 C69B C70B C75B -7.5(8) . . . . ? C38A C39 C38B C60 65(2) . . . . ? C38A C39 C38B C37B -93(2) . . . . ? C38A C37A C42A C43A 81.5(8) . . . . ? C38A C60 C38B C39 -78(2) . . . . ? C38A C60 C38B C37B 80(2) . . . . ? C93 O7 C94 C95 20.5(4) . . . . ? C93 O7 C94 C99 -159.7(3) . . . . ? C93 C71B C70B C69B -179.9(5) . . . . ? C93 C71B C70B C75B -1.0(8) . . . . ? C2 C1 C13 O1 -107.5(3) . . . . ? C2 C3 C20 O2 70.5(4) . . . . ? C2 C3 C4 C5 5.3(4) . . . . ? C2 C3 C4 C9 -177.4(3) . . . . ? C60 O4 C61 C66 -21.7(4) . . . . ? C60 O4 C61 C62 160.3(3) . . . . ? C10 C9 C4 C5 87.0(4) . . . . ? C10 C9 C4 C3 -90.3(4) . . . . ? C42A C37A C38A C39 179.0(8) . . . . ? C42A C37A C38A C60 -7.4(9) . . . . ? C75A C70A C71A C72 -179.7(16) . . . . ? C75A C70A C71A C93 -33.2(19) . . . . ? C75A C70A C69A C68 179.2(14) . . . . ? C75A C70A C69A C86 23.0(19) . . . . ? C42B C37B C36B C35 -175.9(14) . . . . ? C42B C37B C36B C53 -18.8(16) . . . . ? C42B C37B C38B C39 179.6(14) . . . . ? C42B C37B C38B C60 22.6(16) . . . . ? C76A C75A C70A C71A 99.3(16) . . . . ? C76A C75A C70A C69A -82.7(17) . . . . ? C36B C35 C34 C46 -170.2(6) . . . . ? C36B C35 C34 C39 15.5(7) . . . . ? C36B C35 C40 C41 75.2(7) . . . . ? C36B C35 C36A C37A -89.5(18) . . . . ? C36B C35 C36A C53 78.8(18) . . . . ? C36B C37B C42B C43B 82.0(16) . . . . ? C36B C37B C38B C39 2.0(15) . . . . ? C36B C37B C38B C60 -155.1(11) . . . . ? C38B C39 C38A C37A 88(2) . . . . ? C38B C39 C38A C60 -85(2) . . . . ? C38B C37B C42B C43B -95.6(14) . . . . ? C38B C37B C36B C35 1.7(14) . . . . ? C38B C37B C36B C53 158.9(11) . . . . ? C71A C72 C71B C70B -95(3) . . . . ? C71A C72 C71B C93 86(3) . . . . ? C71A C72 C77 C78 76.9(11) . . . . ? C71A C70A C69A C68 -3(2) . . . . ? C71A C70A C69A C86 -159.0(12) . . . . ? C69A C68 C73 C74 -73.1(9) . . . . ? C69A C68 C69B C70B 82(3) . . . . ? C69A C68 C69B C86 -94(3) . . . . ? C69A C70A C71A C72 2(2) . . . . ? C69A C70A C71A C93 148.8(13) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962410' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-gf-118K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-gf, 118 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Br3 O3' _chemical_formula_sum 'C33 H33 Br3 O3' _chemical_formula_weight 717.32 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 19.1589(7) _cell_length_b 13.3863(4) _cell_length_c 25.1489(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.755(4) _cell_angle_gamma 90.00 _cell_volume 6070.3(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 5693 _cell_measurement_temperature 118(2) _cell_measurement_theta_max 29.1714 _cell_measurement_theta_min 3.7085 _exptl_absorpt_coefficient_mu 4.019 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59944 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2880 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_unetI/netI 0.0823 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 38122 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.24 _diffrn_reflns_theta_min 3.72 _diffrn_ambient_temperature 118(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.857 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0295733000 _diffrn_orient_matrix_UB_12 -0.0333421000 _diffrn_orient_matrix_UB_13 0.0131471000 _diffrn_orient_matrix_UB_21 -0.0014683000 _diffrn_orient_matrix_UB_22 0.0136379000 _diffrn_orient_matrix_UB_23 0.0268590000 _diffrn_orient_matrix_UB_31 -0.0258955000 _diffrn_orient_matrix_UB_32 -0.0388612000 _diffrn_orient_matrix_UB_33 -0.0018751000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 9354 _reflns_number_total 14148 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 3.008 _refine_diff_density_min -1.184 _refine_diff_density_rms 0.135 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 14148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0587 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+3.0947P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1247 _refine_ls_wR_factor_ref 0.1471 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C63(H63A,H63B), C47(H47A,H47B), C14(H14A,H14B), C54(H54A, H54B), C61(H61A,H61B), C40(H40A,H40B), C7(H7A,H7B), C30(H30A,H30B), C28(H28A, H28B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C42(H42), C50(H50), C13(H13), C43(H43), C60(H60), C53(H53), C46(H46), C49(H49), C56(H56), C12(H12), C10(H10), C16(H16), C20(H20), C17(H17), C9(H9), C23(H23), C57(H57), C59(H59), C45(H45), C27(H27), C26(H26), C52(H52), C19(H19), C24(H24) 2.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C29(H29A,H29B, H29C), C31(H31A,H31B,H31C), C62(H62A,H62B,H62C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.45283(3) 0.18012(4) 0.71760(2) 0.02938(14) Uani 1 1 d . . . Br5 Br -0.01619(3) 0.15532(4) 0.73532(2) 0.03184(14) Uani 1 1 d . . . Br1 Br 1.02362(3) 1.01075(4) 0.59227(3) 0.03478(15) Uani 1 1 d . . . Br3 Br 0.66253(3) -0.03295(4) 0.22139(2) 0.03087(14) Uani 1 1 d . . . Br6 Br 0.16348(3) -0.06089(5) 0.21147(2) 0.03726(15) Uani 1 1 d . . . Br4 Br 0.53551(3) 1.00831(4) 0.60012(3) 0.04689(19) Uani 1 1 d . . . O5 O 0.18756(16) 0.3005(2) 0.61439(13) 0.0219(7) Uani 1 1 d . . . O2 O 0.68116(16) 0.2971(2) 0.61258(13) 0.0195(7) Uani 1 1 d . . . O1 O 0.90346(17) 0.5904(2) 0.55726(13) 0.0227(7) Uani 1 1 d . . . O3 O 0.76110(18) 0.2284(2) 0.42968(13) 0.0233(7) Uani 1 1 d . . . C4 C 0.8002(2) 0.2452(3) 0.55673(19) 0.0156(9) Uani 1 1 d . . . O4 O 0.41477(17) 0.5878(2) 0.57407(14) 0.0225(7) Uani 1 1 d . . . C37 C 0.2888(2) 0.2550(3) 0.54311(19) 0.0173(9) Uani 1 1 d . . . O6 O 0.23352(17) 0.2254(2) 0.40702(14) 0.0264(8) Uani 1 1 d . . . C41 C 0.4399(2) 0.6839(3) 0.57688(19) 0.0172(9) Uani 1 1 d . . . C5 C 0.8386(2) 0.2791(3) 0.52179(19) 0.0173(9) Uani 1 1 d . . . C1 C 0.8816(2) 0.4239(3) 0.58238(19) 0.0176(9) Uani 1 1 d . . . C3 C 0.8000(2) 0.3044(3) 0.60304(19) 0.0159(9) Uani 1 1 d . . . C48 C 0.1460(2) 0.2656(3) 0.64525(19) 0.0171(9) Uani 1 1 d . . . C55 C 0.2220(3) 0.1615(3) 0.3624(2) 0.0221(10) Uani 1 1 d . . . C42 C 0.4128(3) 0.7540(3) 0.5345(2) 0.0217(10) Uani 1 1 d . . . H42 H 0.3742 0.7363 0.5006 0.026 Uiso 1 1 calc . . R C8 C 0.9366(2) 0.6822(3) 0.56755(19) 0.0158(9) Uani 1 1 d . . . C50 C 0.1261(3) 0.1863(3) 0.7249(2) 0.0230(10) Uani 1 1 d . . . H50 H 0.1449 0.1543 0.7606 0.028 Uiso 1 1 calc . . R C13 C 0.9946(2) 0.7081(3) 0.6159(2) 0.0206(10) Uani 1 1 d . . . H13 H 1.0161 0.6593 0.6441 0.025 Uiso 1 1 calc . . R C43 C 0.4417(3) 0.8504(4) 0.5410(2) 0.0265(11) Uani 1 1 d . . . H43 H 0.4232 0.8986 0.5119 0.032 Uiso 1 1 calc . . R C60 C 0.2777(3) 0.1088(4) 0.3515(2) 0.0261(11) Uani 1 1 d . . . H60 H 0.3279 0.1177 0.3749 0.031 Uiso 1 1 calc . . R C15 C 0.6324(2) 0.2696(3) 0.63921(19) 0.0164(9) Uani 1 1 d . . . C38 C 0.3057(2) 0.2932(3) 0.4963(2) 0.0210(10) Uani 1 1 d . . . C53 C 0.0694(3) 0.2807(4) 0.6202(2) 0.0227(10) Uani 1 1 d . . . H53 H 0.0503 0.3136 0.5848 0.027 Uiso 1 1 calc . . R C51 C 0.0508(3) 0.2008(3) 0.6996(2) 0.0213(10) Uani 1 1 d . . . C46 C 0.4972(2) 0.7101(4) 0.6262(2) 0.0218(10) Uani 1 1 d . . . H46 H 0.5166 0.6619 0.6551 0.026 Uiso 1 1 calc . . R C35 C 0.3131(2) 0.4209(3) 0.5869(2) 0.0190(10) Uani 1 1 d . . . C49 C 0.1745(3) 0.2189(3) 0.69770(19) 0.0214(10) Uani 1 1 d . . . H49 H 0.2265 0.2093 0.7148 0.026 Uiso 1 1 calc . . R C21 C 0.8350(2) 0.2168(4) 0.4709(2) 0.0217(10) Uani 1 1 d . . . H21A H 0.8728 0.2397 0.4548 0.026 Uiso 1 1 calc . . R H21B H 0.8446 0.1457 0.4818 0.026 Uiso 1 1 calc . . R C63 C 0.2654(2) 0.1473(3) 0.5432(2) 0.0188(10) Uani 1 1 d . . . H63A H 0.2386 0.1264 0.5038 0.023 Uiso 1 1 calc . . R H63B H 0.2306 0.1419 0.5645 0.023 Uiso 1 1 calc . . R C56 C 0.1485(3) 0.1478(4) 0.3285(2) 0.0237(11) Uani 1 1 d . . . H56 H 0.1102 0.1833 0.3364 0.028 Uiso 1 1 calc . . R C12 C 1.0215(3) 0.8061(3) 0.6230(2) 0.0221(10) Uani 1 1 d . . . H12 H 1.0607 0.8247 0.6563 0.026 Uiso 1 1 calc . . R C10 C 0.9338(3) 0.8496(3) 0.5318(2) 0.0242(11) Uani 1 1 d . . . H10 H 0.9133 0.8980 0.5032 0.029 Uiso 1 1 calc . . R C22 C 0.7423(2) 0.1654(3) 0.3835(2) 0.0199(10) Uani 1 1 d . . . C58 C 0.1871(3) 0.0304(4) 0.2728(2) 0.0228(10) Uani 1 1 d . . . C16 C 0.5578(3) 0.2901(3) 0.6100(2) 0.0204(10) Uani 1 1 d . . . H16 H 0.5438 0.3211 0.5739 0.024 Uiso 1 1 calc . . R C36 C 0.2927(2) 0.3199(3) 0.58800(19) 0.0168(9) Uani 1 1 d . . . C18 C 0.5253(2) 0.2202(3) 0.6855(2) 0.0198(10) Uani 1 1 d . . . C44 C 0.4980(3) 0.8749(3) 0.5907(2) 0.0275(12) Uani 1 1 d . . . C20 C 0.6529(2) 0.2244(3) 0.69195(19) 0.0191(10) Uani 1 1 d . . . H20 H 0.7036 0.2102 0.7120 0.023 Uiso 1 1 calc . . R C17 C 0.5042(3) 0.2657(3) 0.6331(2) 0.0214(10) Uani 1 1 d . . . H17 H 0.4535 0.2799 0.6132 0.026 Uiso 1 1 calc . . R C9 C 0.9076(2) 0.7524(4) 0.5250(2) 0.0221(10) Uani 1 1 d . . . H9 H 0.8696 0.7336 0.4911 0.026 Uiso 1 1 calc . . R C23 C 0.6677(3) 0.1654(4) 0.3497(2) 0.0260(11) Uani 1 1 d . . . H23 H 0.6334 0.2065 0.3594 0.031 Uiso 1 1 calc . . R C57 C 0.1310(3) 0.0826(4) 0.2833(2) 0.0257(11) Uani 1 1 d . . . H57 H 0.0809 0.0738 0.2597 0.031 Uiso 1 1 calc . . R C25 C 0.6945(3) 0.0459(4) 0.28860(19) 0.0229(11) Uani 1 1 d . . . C59 C 0.2600(3) 0.0427(4) 0.3062(2) 0.0264(11) Uani 1 1 d . . . H59 H 0.2980 0.0063 0.2984 0.032 Uiso 1 1 calc . . R C47 C 0.2666(2) 0.2824(4) 0.63470(19) 0.0195(10) Uani 1 1 d . . . H47A H 0.2773 0.2102 0.6415 0.023 Uiso 1 1 calc . . R H47B H 0.2911 0.3193 0.6702 0.023 Uiso 1 1 calc . . R C14 C 0.7581(2) 0.2689(3) 0.64004(19) 0.0183(10) Uani 1 1 d . . . H14A H 0.7624 0.1955 0.6447 0.022 Uiso 1 1 calc . . R H14B H 0.7780 0.3003 0.6778 0.022 Uiso 1 1 calc . . R C54 C 0.3062(3) 0.2243(3) 0.4495(2) 0.0206(10) Uani 1 1 d . . . H54A H 0.3437 0.2467 0.4330 0.025 Uiso 1 1 calc . . R H54B H 0.3189 0.1557 0.4643 0.025 Uiso 1 1 calc . . R C61 C 0.3223(3) 0.4866(4) 0.6378(2) 0.0252(11) Uani 1 1 d . . . H61A H 0.2816 0.4729 0.6526 0.030 Uiso 1 1 calc . . R H61B H 0.3188 0.5576 0.6261 0.030 Uiso 1 1 calc . . R C45 C 0.5260(3) 0.8059(4) 0.6331(2) 0.0255(11) Uani 1 1 d . . . H45 H 0.5647 0.8238 0.6668 0.031 Uiso 1 1 calc . . R C40 C 0.3415(3) 0.5680(3) 0.5348(2) 0.0223(10) Uani 1 1 d . . . H40A H 0.3392 0.5850 0.4959 0.027 Uiso 1 1 calc . . R H40B H 0.3045 0.6092 0.5443 0.027 Uiso 1 1 calc . . R C34 C 0.3247(2) 0.4586(3) 0.53828(19) 0.0196(10) Uani 1 1 d . . . C7 C 0.9314(3) 0.5153(3) 0.5989(2) 0.0207(10) Uani 1 1 d . . . H7A H 0.9323 0.5404 0.6362 0.025 Uiso 1 1 calc . . R H7B H 0.9826 0.4974 0.6017 0.025 Uiso 1 1 calc . . R C30 C 0.8371(3) 0.4574(3) 0.6649(2) 0.0218(10) Uani 1 1 d . . . H30A H 0.7879 0.4503 0.6692 0.026 Uiso 1 1 calc . . R H30B H 0.8440 0.5286 0.6573 0.026 Uiso 1 1 calc . . R C2 C 0.8392(2) 0.3953(3) 0.61528(19) 0.0176(9) Uani 1 1 d . . . C33 C 0.8161(3) 0.0611(4) 0.5770(2) 0.0294(12) Uani 1 1 d . . . H33A H 0.8590 0.0611 0.5640 0.044 Uiso 1 1 calc . . GR H33B H 0.7908 -0.0036 0.5683 0.044 Uiso 1 1 calc . . GR H33C H 0.8328 0.0725 0.6178 0.044 Uiso 1 1 calc . . GR C27 C 0.7919(3) 0.1054(4) 0.3695(2) 0.0253(11) Uani 1 1 d . . . H27 H 0.8426 0.1049 0.3928 0.030 Uiso 1 1 calc . . R C26 C 0.7682(3) 0.0454(4) 0.3214(2) 0.0276(11) Uani 1 1 d . . . H26 H 0.8025 0.0048 0.3114 0.033 Uiso 1 1 calc . . R C28 C 0.9227(2) 0.4032(4) 0.49718(19) 0.0216(10) Uani 1 1 d . . . H28A H 0.9482 0.3456 0.4871 0.026 Uiso 1 1 calc . . R H28B H 0.9610 0.4518 0.5182 0.026 Uiso 1 1 calc . . R C6 C 0.8806(2) 0.3678(3) 0.53472(19) 0.0168(9) Uani 1 1 d . . . C32 C 0.7624(2) 0.1442(3) 0.5468(2) 0.0198(10) Uani 1 1 d . . . H32A H 0.7430 0.1302 0.5057 0.024 Uiso 1 1 calc . . R H32B H 0.7199 0.1454 0.5607 0.024 Uiso 1 1 calc . . R C11 C 0.9905(2) 0.8753(3) 0.5812(2) 0.0208(10) Uani 1 1 d . . . C64 C 0.3309(3) 0.0755(4) 0.5693(2) 0.0308(12) Uani 1 1 d . . . H64A H 0.3557 0.0929 0.6091 0.046 Uiso 1 1 calc . . GR H64B H 0.3661 0.0813 0.5489 0.046 Uiso 1 1 calc . . GR H64C H 0.3124 0.0068 0.5666 0.046 Uiso 1 1 calc . . GR C52 C 0.0218(3) 0.2474(3) 0.6474(2) 0.0225(10) Uani 1 1 d . . . H52 H -0.0302 0.2564 0.6305 0.027 Uiso 1 1 calc . . R C66 C 0.4114(3) 0.4507(4) 0.4469(2) 0.0366(13) Uani 1 1 d . . . H66A H 0.4371 0.3863 0.4555 0.055 Uiso 1 1 calc . . GR H66B H 0.4336 0.4973 0.4782 0.055 Uiso 1 1 calc . . GR H66C H 0.4161 0.4779 0.4121 0.055 Uiso 1 1 calc . . GR C19 C 0.5986(3) 0.1999(3) 0.71524(19) 0.0201(10) Uani 1 1 d . . . H19 H 0.6121 0.1693 0.7514 0.024 Uiso 1 1 calc . . R C24 C 0.6437(3) 0.1054(4) 0.3022(2) 0.0277(11) Uani 1 1 d . . . H24 H 0.5929 0.1049 0.2791 0.033 Uiso 1 1 calc . . R C29 C 0.8711(3) 0.4524(4) 0.4428(2) 0.0279(11) Uani 1 1 d . . . H29A H 0.9003 0.4742 0.4195 0.042 Uiso 1 1 calc . . GR H29B H 0.8466 0.5103 0.4526 0.042 Uiso 1 1 calc . . GR H29C H 0.8336 0.4041 0.4216 0.042 Uiso 1 1 calc . . GR C31 C 0.8978(3) 0.4260(4) 0.7204(2) 0.0286(12) Uani 1 1 d . . . H31A H 0.9465 0.4300 0.7158 0.043 Uiso 1 1 calc . . GR H31B H 0.8887 0.3573 0.7298 0.043 Uiso 1 1 calc . . GR H31C H 0.8966 0.4708 0.7509 0.043 Uiso 1 1 calc . . GR C65 C 0.3306(3) 0.4364(4) 0.4392(2) 0.0248(11) Uani 1 1 d . . . H65A H 0.3083 0.3898 0.4074 0.030 Uiso 1 1 calc . . R H65B H 0.3046 0.5013 0.4294 0.030 Uiso 1 1 calc . . R C39 C 0.3200(2) 0.3954(3) 0.49220(19) 0.0205(10) Uani 1 1 d . . . C62 C 0.3968(3) 0.4690(4) 0.6848(2) 0.0362(13) Uani 1 1 d . . . H62A H 0.4005 0.5126 0.7170 0.054 Uiso 1 1 calc . . GR H62B H 0.4374 0.4841 0.6706 0.054 Uiso 1 1 calc . . GR H62C H 0.4002 0.3991 0.6970 0.054 Uiso 1 1 calc . . GR 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 Br2 0.0271(3) 0.0401(3) 0.0272(3) 0.0013(2) 0.0174(2) -0.0063(2) Br5 0.0390(3) 0.0312(3) 0.0353(3) 0.0045(2) 0.0256(3) -0.0010(2) Br1 0.0245(3) 0.0132(3) 0.0620(4) -0.0047(2) 0.0086(3) -0.0039(2) Br3 0.0316(3) 0.0376(3) 0.0229(3) -0.0059(2) 0.0086(2) -0.0088(2) Br6 0.0347(3) 0.0526(4) 0.0231(3) -0.0130(3) 0.0079(2) -0.0142(3) Br4 0.0264(3) 0.0165(3) 0.0863(5) -0.0114(3) 0.0042(3) -0.0048(2) O5 0.0170(16) 0.0287(19) 0.0211(18) 0.0096(14) 0.0078(14) 0.0038(14) O2 0.0142(15) 0.0280(19) 0.0180(17) 0.0055(14) 0.0074(13) -0.0017(13) O1 0.0294(18) 0.0139(17) 0.0240(18) 0.0022(14) 0.0080(15) -0.0040(13) O3 0.0281(18) 0.0222(18) 0.0217(18) -0.0057(14) 0.0113(15) 0.0042(14) C4 0.015(2) 0.013(2) 0.020(2) 0.0029(18) 0.0058(18) 0.0004(17) O4 0.0220(17) 0.0147(17) 0.0280(19) -0.0019(14) 0.0048(14) -0.0039(13) C37 0.013(2) 0.014(2) 0.024(3) -0.0001(19) 0.0056(19) 0.0015(17) O6 0.0230(18) 0.0247(19) 0.031(2) -0.0078(15) 0.0090(15) 0.0028(14) C41 0.017(2) 0.016(2) 0.019(2) -0.0051(19) 0.0070(19) -0.0017(18) C5 0.017(2) 0.016(2) 0.018(2) -0.0030(19) 0.0051(19) 0.0019(18) C1 0.017(2) 0.016(2) 0.019(2) 0.0003(19) 0.0053(19) 0.0000(18) C3 0.011(2) 0.016(2) 0.022(2) 0.0014(19) 0.0061(18) 0.0023(17) C48 0.019(2) 0.014(2) 0.022(3) -0.0018(19) 0.012(2) -0.0005(18) C55 0.025(2) 0.019(3) 0.024(3) -0.001(2) 0.012(2) -0.002(2) C42 0.024(2) 0.015(2) 0.024(3) -0.004(2) 0.004(2) -0.0032(19) C8 0.014(2) 0.014(2) 0.020(2) -0.0040(19) 0.0066(18) -0.0014(17) C50 0.032(3) 0.018(2) 0.021(3) -0.001(2) 0.011(2) 0.002(2) C13 0.021(2) 0.020(3) 0.021(3) 0.002(2) 0.006(2) -0.0008(19) C43 0.024(3) 0.015(2) 0.037(3) -0.001(2) 0.007(2) -0.002(2) C60 0.016(2) 0.030(3) 0.032(3) -0.008(2) 0.008(2) -0.005(2) C15 0.020(2) 0.014(2) 0.017(2) -0.0017(18) 0.0081(19) -0.0035(18) C38 0.021(2) 0.017(2) 0.025(3) -0.004(2) 0.007(2) 0.0012(19) C53 0.022(2) 0.025(3) 0.020(3) 0.003(2) 0.006(2) 0.002(2) C51 0.029(3) 0.016(2) 0.025(3) -0.007(2) 0.017(2) -0.0065(19) C46 0.022(2) 0.022(3) 0.021(3) -0.002(2) 0.007(2) 0.0008(19) C35 0.013(2) 0.018(2) 0.027(3) -0.007(2) 0.0073(19) 0.0038(18) C49 0.028(3) 0.019(3) 0.019(3) 0.001(2) 0.010(2) 0.000(2) C21 0.019(2) 0.021(3) 0.025(3) -0.002(2) 0.007(2) 0.0021(19) C63 0.019(2) 0.012(2) 0.024(3) -0.0023(19) 0.0040(19) -0.0039(18) C56 0.019(2) 0.023(3) 0.028(3) 0.008(2) 0.006(2) 0.004(2) C12 0.019(2) 0.022(3) 0.024(3) -0.007(2) 0.005(2) -0.0064(19) C10 0.022(2) 0.015(2) 0.036(3) 0.004(2) 0.010(2) -0.0022(19) C22 0.021(2) 0.019(3) 0.021(2) 0.005(2) 0.009(2) 0.0019(19) C58 0.027(3) 0.025(3) 0.019(2) -0.004(2) 0.010(2) -0.011(2) C16 0.023(2) 0.022(3) 0.019(2) 0.003(2) 0.010(2) 0.0003(19) C36 0.011(2) 0.017(2) 0.020(2) -0.0019(19) 0.0030(18) -0.0011(17) C18 0.022(2) 0.019(2) 0.024(3) -0.009(2) 0.017(2) -0.0048(19) C44 0.019(2) 0.012(2) 0.051(3) -0.008(2) 0.011(2) -0.0021(19) C20 0.016(2) 0.020(2) 0.022(3) -0.002(2) 0.0081(19) -0.0035(18) C17 0.018(2) 0.025(3) 0.022(3) -0.002(2) 0.008(2) -0.0009(19) C9 0.019(2) 0.022(3) 0.024(3) 0.000(2) 0.004(2) -0.0017(19) C23 0.026(3) 0.028(3) 0.025(3) 0.004(2) 0.010(2) 0.010(2) C57 0.017(2) 0.029(3) 0.028(3) 0.004(2) 0.003(2) -0.004(2) C25 0.027(3) 0.025(3) 0.019(2) 0.000(2) 0.010(2) -0.008(2) C59 0.020(2) 0.032(3) 0.028(3) -0.008(2) 0.009(2) -0.002(2) C47 0.016(2) 0.022(3) 0.017(2) -0.0008(19) 0.0004(19) 0.0015(18) C14 0.012(2) 0.021(3) 0.020(2) -0.0001(19) 0.0031(18) 0.0018(18) C54 0.024(2) 0.017(2) 0.023(3) -0.005(2) 0.011(2) -0.0031(19) C61 0.031(3) 0.020(3) 0.026(3) -0.007(2) 0.010(2) 0.001(2) C45 0.019(2) 0.025(3) 0.028(3) -0.012(2) 0.003(2) -0.004(2) C40 0.023(2) 0.019(3) 0.022(3) -0.003(2) 0.003(2) -0.001(2) C34 0.018(2) 0.019(2) 0.022(3) 0.000(2) 0.0065(19) -0.0016(18) C7 0.022(2) 0.017(2) 0.022(3) 0.004(2) 0.006(2) 0.0011(19) C30 0.018(2) 0.020(3) 0.027(3) -0.006(2) 0.009(2) -0.0036(19) C2 0.015(2) 0.019(2) 0.019(2) -0.0009(19) 0.0058(19) -0.0019(18) C33 0.037(3) 0.014(3) 0.034(3) 0.002(2) 0.008(2) 0.002(2) C27 0.018(2) 0.029(3) 0.030(3) -0.009(2) 0.010(2) -0.002(2) C26 0.023(3) 0.030(3) 0.033(3) -0.006(2) 0.014(2) 0.001(2) C28 0.021(2) 0.024(3) 0.022(3) -0.001(2) 0.011(2) 0.001(2) C6 0.015(2) 0.017(2) 0.019(2) 0.0032(19) 0.0050(18) 0.0033(18) C32 0.020(2) 0.016(2) 0.022(3) -0.005(2) 0.005(2) -0.0081(18) C11 0.015(2) 0.012(2) 0.037(3) -0.006(2) 0.011(2) -0.0035(18) C64 0.038(3) 0.016(3) 0.033(3) 0.000(2) 0.004(2) 0.002(2) C52 0.021(2) 0.022(3) 0.028(3) -0.003(2) 0.014(2) -0.002(2) C66 0.039(3) 0.036(3) 0.040(3) -0.003(3) 0.021(3) -0.008(3) C19 0.026(3) 0.017(2) 0.018(2) -0.0017(19) 0.008(2) -0.0037(19) C24 0.025(3) 0.028(3) 0.031(3) 0.011(2) 0.010(2) 0.003(2) C29 0.036(3) 0.029(3) 0.018(3) 0.005(2) 0.007(2) -0.002(2) C31 0.029(3) 0.028(3) 0.025(3) -0.009(2) 0.004(2) -0.001(2) C65 0.029(3) 0.025(3) 0.019(3) -0.003(2) 0.007(2) 0.000(2) C39 0.018(2) 0.020(3) 0.022(3) -0.004(2) 0.0051(19) -0.0019(19) C62 0.048(3) 0.026(3) 0.028(3) -0.010(2) 0.004(3) -0.006(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 Br2 C18 1.904(4) . ? Br5 C51 1.899(4) . ? Br1 C11 1.910(4) . ? Br3 C25 1.910(5) . ? Br6 C58 1.899(5) . ? Br4 C44 1.910(5) . ? O5 C48 1.368(5) . ? O5 C47 1.446(5) . ? O2 C15 1.371(5) . ? O2 C14 1.450(5) . ? O1 C8 1.367(5) . ? O1 C7 1.420(5) . ? O3 C21 1.453(5) . ? O3 C22 1.381(6) . ? C4 C5 1.399(6) . ? C4 C3 1.409(6) . ? C4 C32 1.514(6) . ? O4 C41 1.367(5) . ? O4 C40 1.443(5) . ? C37 C38 1.417(6) . ? C37 C63 1.509(6) . ? C37 C36 1.406(6) . ? O6 C55 1.367(5) . ? O6 C54 1.440(5) . ? C41 C42 1.384(6) . ? C41 C46 1.395(6) . ? C5 C21 1.510(6) . ? C5 C6 1.409(6) . ? C1 C7 1.520(6) . ? C1 C2 1.395(6) . ? C1 C6 1.410(6) . ? C3 C14 1.498(6) . ? C3 C2 1.408(6) . ? C48 C53 1.403(6) . ? C48 C49 1.393(6) . ? C55 C60 1.383(6) . ? C55 C56 1.390(6) . ? C42 H42 0.9500 . ? C42 C43 1.392(6) . ? C8 C13 1.385(6) . ? C8 C9 1.391(6) . ? C50 H50 0.9500 . ? C50 C51 1.380(7) . ? C50 C49 1.394(6) . ? C13 H13 0.9500 . ? C13 C12 1.399(6) . ? C43 H43 0.9500 . ? C43 C44 1.387(7) . ? C60 H60 0.9500 . ? C60 C59 1.392(7) . ? C15 C16 1.396(6) . ? C15 C20 1.388(6) . ? C38 C54 1.498(6) . ? C38 C39 1.406(6) . ? C53 H53 0.9500 . ? C53 C52 1.385(6) . ? C51 C52 1.389(7) . ? C46 H46 0.9500 . ? C46 C45 1.384(6) . ? C35 C36 1.410(6) . ? C35 C61 1.514(6) . ? C35 C34 1.408(6) . ? C49 H49 0.9500 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C63 C64 1.539(6) . ? C56 H56 0.9500 . ? C56 C57 1.382(7) . ? C12 H12 0.9500 . ? C12 C11 1.378(7) . ? C10 H10 0.9500 . ? C10 C9 1.384(6) . ? C10 C11 1.387(7) . ? C22 C23 1.394(6) . ? C22 C27 1.378(6) . ? C58 C57 1.381(7) . ? C58 C59 1.375(6) . ? C16 H16 0.9500 . ? C16 C17 1.379(6) . ? C36 C47 1.509(6) . ? C18 C17 1.384(7) . ? C18 C19 1.376(6) . ? C44 C45 1.374(7) . ? C20 H20 0.9500 . ? C20 C19 1.395(6) . ? C17 H17 0.9500 . ? C9 H9 0.9500 . ? C23 H23 0.9500 . ? C23 C24 1.384(7) . ? C57 H57 0.9500 . ? C25 C26 1.374(7) . ? C25 C24 1.386(7) . ? C59 H59 0.9500 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C61 C62 1.532(7) . ? C45 H45 0.9500 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C40 C34 1.509(6) . ? C34 C39 1.413(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 C2 1.510(6) . ? C30 C31 1.542(7) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C33 C32 1.531(7) . ? C27 H27 0.9500 . ? C27 C26 1.394(7) . ? C26 H26 0.9500 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C6 1.510(6) . ? C28 C29 1.540(6) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C52 H52 0.9500 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C66 C65 1.506(7) . ? C19 H19 0.9500 . ? C24 H24 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C65 C39 1.518(6) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? 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 C48 O5 C47 118.9(3) . . ? C15 O2 C14 116.6(3) . . ? C8 O1 C7 117.5(4) . . ? C22 O3 C21 116.7(3) . . ? C5 C4 C3 119.0(4) . . ? C5 C4 C32 120.6(4) . . ? C3 C4 C32 120.3(4) . . ? C41 O4 C40 116.9(3) . . ? C38 C37 C63 119.8(4) . . ? C36 C37 C38 118.6(4) . . ? C36 C37 C63 121.7(4) . . ? C55 O6 C54 116.7(3) . . ? O4 C41 C42 124.4(4) . . ? O4 C41 C46 116.1(4) . . ? C42 C41 C46 119.5(4) . . ? C4 C5 C21 118.1(4) . . ? C4 C5 C6 120.6(4) . . ? C6 C5 C21 121.3(4) . . ? C2 C1 C7 119.8(4) . . ? C2 C1 C6 121.0(4) . . ? C6 C1 C7 119.2(4) . . ? C4 C3 C14 119.1(4) . . ? C2 C3 C4 121.1(4) . . ? C2 C3 C14 119.8(4) . . ? O5 C48 C53 114.6(4) . . ? O5 C48 C49 125.0(4) . . ? C49 C48 C53 120.4(4) . . ? O6 C55 C60 124.1(4) . . ? O6 C55 C56 115.8(4) . . ? C60 C55 C56 120.1(4) . . ? C41 C42 H42 119.8 . . ? C41 C42 C43 120.4(4) . . ? C43 C42 H42 119.8 . . ? O1 C8 C13 125.1(4) . . ? O1 C8 C9 115.0(4) . . ? C13 C8 C9 119.9(4) . . ? C51 C50 H50 120.1 . . ? C51 C50 C49 119.7(4) . . ? C49 C50 H50 120.1 . . ? C8 C13 H13 120.0 . . ? C8 C13 C12 120.0(4) . . ? C12 C13 H13 120.0 . . ? C42 C43 H43 120.5 . . ? C44 C43 C42 118.9(5) . . ? C44 C43 H43 120.5 . . ? C55 C60 H60 120.1 . . ? C55 C60 C59 119.8(4) . . ? C59 C60 H60 120.1 . . ? O2 C15 C16 115.8(4) . . ? O2 C15 C20 124.4(4) . . ? C20 C15 C16 119.8(4) . . ? C37 C38 C54 119.6(4) . . ? C39 C38 C37 121.2(4) . . ? C39 C38 C54 119.1(4) . . ? C48 C53 H53 120.1 . . ? C52 C53 C48 119.7(4) . . ? C52 C53 H53 120.1 . . ? C50 C51 Br5 120.4(4) . . ? C50 C51 C52 121.3(4) . . ? C52 C51 Br5 118.2(4) . . ? C41 C46 H46 119.8 . . ? C45 C46 C41 120.4(4) . . ? C45 C46 H46 119.8 . . ? C36 C35 C61 119.6(4) . . ? C34 C35 C36 119.1(4) . . ? C34 C35 C61 121.3(4) . . ? C48 C49 C50 119.4(4) . . ? C48 C49 H49 120.3 . . ? C50 C49 H49 120.3 . . ? O3 C21 C5 107.4(3) . . ? O3 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C5 C21 H21A 110.2 . . ? C5 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C37 C63 H63A 108.9 . . ? C37 C63 H63B 108.9 . . ? C37 C63 C64 113.4(4) . . ? H63A C63 H63B 107.7 . . ? C64 C63 H63A 108.9 . . ? C64 C63 H63B 108.9 . . ? C55 C56 H56 119.9 . . ? C57 C56 C55 120.2(4) . . ? C57 C56 H56 119.9 . . ? C13 C12 H12 120.4 . . ? C11 C12 C13 119.1(4) . . ? C11 C12 H12 120.4 . . ? C9 C10 H10 120.5 . . ? C9 C10 C11 119.1(4) . . ? C11 C10 H10 120.5 . . ? O3 C22 C23 115.8(4) . . ? C27 C22 O3 124.4(4) . . ? C27 C22 C23 119.9(4) . . ? C57 C58 Br6 119.6(4) . . ? C59 C58 Br6 119.2(4) . . ? C59 C58 C57 121.3(4) . . ? C15 C16 H16 119.7 . . ? C17 C16 C15 120.5(4) . . ? C17 C16 H16 119.7 . . ? C37 C36 C35 121.1(4) . . ? C37 C36 C47 118.5(4) . . ? C35 C36 C47 120.1(4) . . ? C17 C18 Br2 120.5(3) . . ? C19 C18 Br2 118.1(4) . . ? C19 C18 C17 121.4(4) . . ? C43 C44 Br4 118.5(4) . . ? C45 C44 Br4 120.1(4) . . ? C45 C44 C43 121.4(4) . . ? C15 C20 H20 120.2 . . ? C15 C20 C19 119.6(4) . . ? C19 C20 H20 120.2 . . ? C16 C17 C18 119.1(4) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C8 C9 H9 119.8 . . ? C10 C9 C8 120.4(4) . . ? C10 C9 H9 119.8 . . ? C22 C23 H23 120.0 . . ? C24 C23 C22 120.0(4) . . ? C24 C23 H23 120.0 . . ? C56 C57 H57 120.4 . . ? C58 C57 C56 119.3(4) . . ? C58 C57 H57 120.4 . . ? C26 C25 Br3 119.0(4) . . ? C26 C25 C24 121.4(5) . . ? C24 C25 Br3 119.6(4) . . ? C60 C59 H59 120.3 . . ? C58 C59 C60 119.5(4) . . ? C58 C59 H59 120.3 . . ? O5 C47 C36 104.6(3) . . ? O5 C47 H47A 110.8 . . ? O5 C47 H47B 110.8 . . ? C36 C47 H47A 110.8 . . ? C36 C47 H47B 110.8 . . ? H47A C47 H47B 108.9 . . ? O2 C14 C3 107.1(3) . . ? O2 C14 H14A 110.3 . . ? O2 C14 H14B 110.3 . . ? C3 C14 H14A 110.3 . . ? C3 C14 H14B 110.3 . . ? H14A C14 H14B 108.6 . . ? O6 C54 C38 108.4(4) . . ? O6 C54 H54A 110.0 . . ? O6 C54 H54B 110.0 . . ? C38 C54 H54A 110.0 . . ? C38 C54 H54B 110.0 . . ? H54A C54 H54B 108.4 . . ? C35 C61 H61A 109.2 . . ? C35 C61 H61B 109.2 . . ? C35 C61 C62 112.1(4) . . ? H61A C61 H61B 107.9 . . ? C62 C61 H61A 109.2 . . ? C62 C61 H61B 109.2 . . ? C46 C45 H45 120.3 . . ? C44 C45 C46 119.4(5) . . ? C44 C45 H45 120.3 . . ? O4 C40 H40A 110.0 . . ? O4 C40 H40B 110.0 . . ? O4 C40 C34 108.4(4) . . ? H40A C40 H40B 108.4 . . ? C34 C40 H40A 110.0 . . ? C34 C40 H40B 110.0 . . ? C35 C34 C40 119.9(4) . . ? C35 C34 C39 120.9(4) . . ? C39 C34 C40 119.3(4) . . ? O1 C7 C1 108.8(4) . . ? O1 C7 H7A 109.9 . . ? O1 C7 H7B 109.9 . . ? C1 C7 H7A 109.9 . . ? C1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? H30A C30 H30B 107.9 . . ? C2 C30 H30A 109.2 . . ? C2 C30 H30B 109.2 . . ? C2 C30 C31 112.1(4) . . ? C31 C30 H30A 109.2 . . ? C31 C30 H30B 109.2 . . ? C1 C2 C3 118.8(4) . . ? C1 C2 C30 121.4(4) . . ? C3 C2 C30 119.7(4) . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? C22 C27 H27 119.8 . . ? C22 C27 C26 120.5(4) . . ? C26 C27 H27 119.8 . . ? C25 C26 C27 119.0(4) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? H28A C28 H28B 107.9 . . ? C6 C28 H28A 109.3 . . ? C6 C28 H28B 109.3 . . ? C6 C28 C29 111.8(4) . . ? C29 C28 H28A 109.3 . . ? C29 C28 H28B 109.3 . . ? C5 C6 C1 119.2(4) . . ? C5 C6 C28 120.3(4) . . ? C1 C6 C28 120.5(4) . . ? C4 C32 C33 111.3(4) . . ? C4 C32 H32A 109.4 . . ? C4 C32 H32B 109.4 . . ? C33 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C12 C11 Br1 119.3(4) . . ? C12 C11 C10 121.4(4) . . ? C10 C11 Br1 119.2(4) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C53 C52 C51 119.4(4) . . ? C53 C52 H52 120.3 . . ? C51 C52 H52 120.3 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? C18 C19 C20 119.6(4) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C23 C24 C25 119.3(5) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C66 C65 H65A 109.3 . . ? C66 C65 H65B 109.3 . . ? C66 C65 C39 111.7(4) . . ? H65A C65 H65B 107.9 . . ? C39 C65 H65A 109.3 . . ? C39 C65 H65B 109.3 . . ? C38 C39 C34 118.8(4) . . ? C38 C39 C65 120.3(4) . . ? C34 C39 C65 120.9(4) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 -177.3(3) . . . . ? Br2 C18 C19 C20 177.3(3) . . . . ? Br5 C51 C52 C53 -179.6(3) . . . . ? Br3 C25 C26 C27 178.0(4) . . . . ? Br3 C25 C24 C23 -177.5(4) . . . . ? Br6 C58 C57 C56 179.1(4) . . . . ? Br6 C58 C59 C60 -179.5(4) . . . . ? Br4 C44 C45 C46 178.7(3) . . . . ? O5 C48 C53 C52 179.3(4) . . . . ? O5 C48 C49 C50 -179.8(4) . . . . ? O2 C15 C16 C17 -179.8(4) . . . . ? O2 C15 C20 C19 179.7(4) . . . . ? O1 C8 C13 C12 -176.6(4) . . . . ? O1 C8 C9 C10 176.5(4) . . . . ? O3 C22 C23 C24 179.4(4) . . . . ? O3 C22 C27 C26 -178.8(4) . . . . ? C4 C5 C21 O3 72.7(5) . . . . ? C4 C5 C6 C1 -2.1(6) . . . . ? C4 C5 C6 C28 179.2(4) . . . . ? C4 C3 C14 O2 -82.8(5) . . . . ? C4 C3 C2 C1 -3.3(6) . . . . ? C4 C3 C2 C30 179.3(4) . . . . ? O4 C41 C42 C43 180.0(4) . . . . ? O4 C41 C46 C45 -179.6(4) . . . . ? O4 C40 C34 C35 69.8(5) . . . . ? O4 C40 C34 C39 -110.8(4) . . . . ? C37 C38 C54 O6 92.0(5) . . . . ? C37 C38 C39 C34 6.3(7) . . . . ? C37 C38 C39 C65 -174.1(4) . . . . ? C37 C36 C47 O5 -85.6(5) . . . . ? O6 C55 C60 C59 177.6(4) . . . . ? O6 C55 C56 C57 -178.2(4) . . . . ? C41 O4 C40 C34 -180.0(3) . . . . ? C41 C42 C43 C44 0.0(7) . . . . ? C41 C46 C45 C44 -0.6(7) . . . . ? C5 C4 C3 C14 179.2(4) . . . . ? C5 C4 C3 C2 -1.4(6) . . . . ? C5 C4 C32 C33 86.7(5) . . . . ? C3 C4 C5 C21 -177.2(4) . . . . ? C3 C4 C5 C6 4.1(6) . . . . ? C3 C4 C32 C33 -90.3(5) . . . . ? C48 O5 C47 C36 173.8(4) . . . . ? C48 C53 C52 C51 1.0(7) . . . . ? C55 O6 C54 C38 -175.8(4) . . . . ? C55 C60 C59 C58 -0.1(8) . . . . ? C55 C56 C57 C58 0.9(7) . . . . ? C42 C41 C46 C45 1.1(7) . . . . ? C42 C43 C44 Br4 -178.4(3) . . . . ? C42 C43 C44 C45 0.6(7) . . . . ? C8 O1 C7 C1 173.6(3) . . . . ? C8 C13 C12 C11 -1.0(7) . . . . ? C50 C51 C52 C53 -0.4(7) . . . . ? C13 C8 C9 C10 -3.2(7) . . . . ? C13 C12 C11 Br1 176.9(3) . . . . ? C13 C12 C11 C10 -0.9(7) . . . . ? C43 C44 C45 C46 -0.3(7) . . . . ? C60 C55 C56 C57 -1.0(7) . . . . ? C15 O2 C14 C3 178.7(3) . . . . ? C15 C16 C17 C18 -0.3(7) . . . . ? C15 C20 C19 C18 0.4(7) . . . . ? C38 C37 C63 C64 90.1(5) . . . . ? C38 C37 C36 C35 -0.1(6) . . . . ? C38 C37 C36 C47 173.3(4) . . . . ? C53 C48 C49 C50 0.7(7) . . . . ? C51 C50 C49 C48 -0.1(7) . . . . ? C46 C41 C42 C43 -0.8(7) . . . . ? C35 C36 C47 O5 87.9(5) . . . . ? C35 C34 C39 C38 -1.8(7) . . . . ? C35 C34 C39 C65 178.5(4) . . . . ? C49 C48 C53 C52 -1.2(7) . . . . ? C49 C50 C51 Br5 179.1(3) . . . . ? C49 C50 C51 C52 0.0(7) . . . . ? C21 O3 C22 C23 169.2(4) . . . . ? C21 O3 C22 C27 -11.2(6) . . . . ? C21 C5 C6 C1 179.3(4) . . . . ? C21 C5 C6 C28 0.7(6) . . . . ? C63 C37 C38 C54 -4.9(6) . . . . ? C63 C37 C38 C39 173.3(4) . . . . ? C63 C37 C36 C35 -178.6(4) . . . . ? C63 C37 C36 C47 -5.2(6) . . . . ? C56 C55 C60 C59 0.6(7) . . . . ? C22 O3 C21 C5 -170.2(4) . . . . ? C22 C23 C24 C25 -0.1(7) . . . . ? C22 C27 C26 C25 -1.0(7) . . . . ? C16 C15 C20 C19 0.0(7) . . . . ? C36 C37 C38 C54 176.5(4) . . . . ? C36 C37 C38 C39 -5.3(7) . . . . ? C36 C37 C63 C64 -91.4(5) . . . . ? C36 C35 C61 C62 78.8(5) . . . . ? C36 C35 C34 C40 175.9(4) . . . . ? C36 C35 C34 C39 -3.4(6) . . . . ? C20 C15 C16 C17 0.0(7) . . . . ? C17 C18 C19 C20 -0.7(7) . . . . ? C9 C8 C13 C12 3.1(6) . . . . ? C9 C10 C11 Br1 -177.1(3) . . . . ? C9 C10 C11 C12 0.7(7) . . . . ? C23 C22 C27 C26 0.8(7) . . . . ? C57 C58 C59 C60 0.1(8) . . . . ? C59 C58 C57 C56 -0.5(7) . . . . ? C47 O5 C48 C53 -175.8(4) . . . . ? C47 O5 C48 C49 4.7(6) . . . . ? C14 O2 C15 C16 -174.9(4) . . . . ? C14 O2 C15 C20 5.3(6) . . . . ? C14 C3 C2 C1 176.1(4) . . . . ? C14 C3 C2 C30 -1.3(6) . . . . ? C54 O6 C55 C60 -10.4(6) . . . . ? C54 O6 C55 C56 166.8(4) . . . . ? C54 C38 C39 C34 -175.6(4) . . . . ? C54 C38 C39 C65 4.1(6) . . . . ? C61 C35 C36 C37 -175.4(4) . . . . ? C61 C35 C36 C47 11.3(6) . . . . ? C61 C35 C34 C40 -4.3(6) . . . . ? C61 C35 C34 C39 176.4(4) . . . . ? C40 O4 C41 C42 -21.7(6) . . . . ? C40 O4 C41 C46 159.0(4) . . . . ? C40 C34 C39 C38 178.8(4) . . . . ? C40 C34 C39 C65 -0.8(6) . . . . ? C34 C35 C36 C37 4.3(6) . . . . ? C34 C35 C36 C47 -169.0(4) . . . . ? C34 C35 C61 C62 -101.0(5) . . . . ? C7 O1 C8 C13 -1.1(6) . . . . ? C7 O1 C8 C9 179.2(4) . . . . ? C7 C1 C2 C3 -172.8(4) . . . . ? C7 C1 C2 C30 4.5(6) . . . . ? C7 C1 C6 C5 175.5(4) . . . . ? C7 C1 C6 C28 -5.9(6) . . . . ? C2 C1 C7 O1 -113.1(4) . . . . ? C2 C1 C6 C5 -2.7(6) . . . . ? C2 C1 C6 C28 175.9(4) . . . . ? C2 C3 C14 O2 97.8(5) . . . . ? C27 C22 C23 C24 -0.2(7) . . . . ? C26 C25 C24 C23 0.0(7) . . . . ? C6 C5 C21 O3 -108.7(5) . . . . ? C6 C1 C7 O1 68.7(5) . . . . ? C6 C1 C2 C3 5.4(6) . . . . ? C6 C1 C2 C30 -177.3(4) . . . . ? C32 C4 C5 C21 5.8(6) . . . . ? C32 C4 C5 C6 -172.8(4) . . . . ? C32 C4 C3 C14 -3.8(6) . . . . ? C32 C4 C3 C2 175.6(4) . . . . ? C11 C10 C9 C8 1.3(7) . . . . ? C66 C65 C39 C38 -100.4(5) . . . . ? C66 C65 C39 C34 79.2(6) . . . . ? C19 C18 C17 C16 0.7(7) . . . . ? C24 C25 C26 C27 0.6(7) . . . . ? C29 C28 C6 C5 77.2(5) . . . . ? C29 C28 C6 C1 -101.4(5) . . . . ? C31 C30 C2 C1 -90.3(5) . . . . ? C31 C30 C2 C3 87.0(5) . . . . ? C39 C38 C54 O6 -86.2(5) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962411' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-gf-154K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-gf, 154 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Br3 O3' _chemical_formula_sum 'C33 H33 Br3 O3' _chemical_formula_weight 717.32 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 19.1937(7) _cell_length_b 13.4082(4) _cell_length_c 25.1997(11) _cell_angle_alpha 90.00 _cell_angle_beta 109.775(4) _cell_angle_gamma 90.00 _cell_volume 6102.8(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4984 _cell_measurement_temperature 154(2) _cell_measurement_theta_max 29.0860 _cell_measurement_theta_min 3.7023 _exptl_absorpt_coefficient_mu 3.998 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.53765 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2880 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_unetI/netI 0.0913 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 38033 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.15 _diffrn_reflns_theta_min 3.71 _diffrn_ambient_temperature 154(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0295150000 _diffrn_orient_matrix_UB_12 -0.0332646000 _diffrn_orient_matrix_UB_13 0.0132008000 _diffrn_orient_matrix_UB_21 -0.0016192000 _diffrn_orient_matrix_UB_22 0.0135756000 _diffrn_orient_matrix_UB_23 0.0267669000 _diffrn_orient_matrix_UB_31 -0.0258467000 _diffrn_orient_matrix_UB_32 -0.0388352000 _diffrn_orient_matrix_UB_33 -0.0019677000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 8636 _reflns_number_total 14202 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 2.329 _refine_diff_density_min -1.151 _refine_diff_density_rms 0.128 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 14202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1250 _refine_ls_R_factor_gt 0.0638 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+2.8569P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1303 _refine_ls_wR_factor_ref 0.1569 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C63(H63A,H63B), C47(H47A,H47B), C14(H14A,H14B), C54(H54A, H54B), C61(H61A,H61B), C40(H40A,H40B), C7(H7A,H7B), C30(H30A,H30B), C28(H28A, H28B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C42(H42), C50(H50), C13(H13), C43(H43), C60(H60), C53(H53), C46(H46), C49(H49), C56(H56), C12(H12), C10(H10), C16(H16), C20(H20), C17(H17), C9(H9), C23(H23), C57(H57), C59(H59), C45(H45), C27(H27), C26(H26), C52(H52), C19(H19), C24(H24) 2.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C29(H29A,H29B, H29C), C31(H31A,H31B,H31C), C62(H62A,H62B,H62C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.45363(3) 0.17991(4) 0.71724(2) 0.03705(16) Uani 1 1 d . . . Br5 Br -0.01587(3) 0.15565(4) 0.73501(3) 0.04000(17) Uani 1 1 d . . . Br1 Br 1.02365(3) 1.00964(4) 0.59237(3) 0.04393(18) Uani 1 1 d . . . Br3 Br 0.66238(3) -0.03229(5) 0.22171(2) 0.03908(16) Uani 1 1 d . . . Br6 Br 0.16312(3) -0.05920(5) 0.21172(2) 0.04697(18) Uani 1 1 d . . . Br4 Br 0.53534(3) 1.00677(4) 0.60039(4) 0.0597(2) Uani 1 1 d . . . O5 O 0.18778(17) 0.2997(3) 0.61427(14) 0.0270(8) Uani 1 1 d . . . O2 O 0.68136(17) 0.2967(2) 0.61245(14) 0.0245(8) Uani 1 1 d . . . O1 O 0.90345(18) 0.5900(2) 0.55760(14) 0.0272(8) Uani 1 1 d . . . O3 O 0.76099(19) 0.2289(3) 0.42924(14) 0.0294(8) Uani 1 1 d . . . C4 C 0.8004(2) 0.2458(3) 0.5565(2) 0.0204(10) Uani 1 1 d . . . O4 O 0.41509(18) 0.5872(2) 0.57414(15) 0.0287(8) Uani 1 1 d . . . C37 C 0.2894(2) 0.2554(3) 0.5432(2) 0.0201(10) Uani 1 1 d . . . O6 O 0.23394(18) 0.2251(3) 0.40751(15) 0.0316(9) Uani 1 1 d . . . C41 C 0.4400(3) 0.6832(3) 0.5771(2) 0.0218(11) Uani 1 1 d . . . C5 C 0.8387(3) 0.2796(3) 0.5216(2) 0.0226(11) Uani 1 1 d . . . C1 C 0.8813(3) 0.4237(4) 0.5821(2) 0.0224(10) Uani 1 1 d . . . C3 C 0.8000(2) 0.3044(3) 0.6027(2) 0.0199(10) Uani 1 1 d . . . C48 C 0.1461(3) 0.2652(3) 0.6451(2) 0.0219(11) Uani 1 1 d . . . C55 C 0.2222(3) 0.1616(3) 0.3630(2) 0.0241(11) Uani 1 1 d . . . C42 C 0.4126(3) 0.7532(4) 0.5348(2) 0.0265(11) Uani 1 1 d . . . H42 H 0.3738 0.7359 0.5011 0.032 Uiso 1 1 calc . . R C8 C 0.9366(2) 0.6818(3) 0.5677(2) 0.0207(10) Uani 1 1 d . . . C50 C 0.1261(3) 0.1859(4) 0.7242(2) 0.0272(11) Uani 1 1 d . . . H50 H 0.1448 0.1532 0.7596 0.033 Uiso 1 1 calc . . R C13 C 0.9946(3) 0.7073(4) 0.6161(2) 0.0259(11) Uani 1 1 d . . . H13 H 1.0158 0.6589 0.6445 0.031 Uiso 1 1 calc . . R C43 C 0.4421(3) 0.8491(4) 0.5418(2) 0.0323(13) Uani 1 1 d . . . H43 H 0.4237 0.8974 0.5128 0.039 Uiso 1 1 calc . . R C60 C 0.2778(3) 0.1090(4) 0.3516(2) 0.0321(13) Uani 1 1 d . . . H60 H 0.3280 0.1181 0.3748 0.039 Uiso 1 1 calc . . R C15 C 0.6329(3) 0.2695(3) 0.6392(2) 0.0200(10) Uani 1 1 d . . . C38 C 0.3059(3) 0.2927(4) 0.4967(2) 0.0253(11) Uani 1 1 d . . . C53 C 0.0696(3) 0.2800(4) 0.6200(2) 0.0256(11) Uani 1 1 d . . . H53 H 0.0504 0.3124 0.5844 0.031 Uiso 1 1 calc . . R C51 C 0.0510(3) 0.2009(4) 0.6992(2) 0.0276(12) Uani 1 1 d . . . C46 C 0.4969(3) 0.7091(4) 0.6265(2) 0.0281(12) Uani 1 1 d . . . H46 H 0.5159 0.6613 0.6556 0.034 Uiso 1 1 calc . . R C35 C 0.3129(2) 0.4203(4) 0.5869(2) 0.0231(11) Uani 1 1 d . . . C49 C 0.1745(3) 0.2189(4) 0.6974(2) 0.0253(11) Uani 1 1 d . . . H49 H 0.2264 0.2098 0.7146 0.030 Uiso 1 1 calc . . R C21 C 0.8351(3) 0.2178(4) 0.4706(2) 0.0259(11) Uani 1 1 d . . . H21A H 0.8726 0.2412 0.4545 0.031 Uiso 1 1 calc . . R H21B H 0.8450 0.1469 0.4813 0.031 Uiso 1 1 calc . . R C63 C 0.2657(3) 0.1476(3) 0.5431(2) 0.0252(11) Uani 1 1 d . . . H63A H 0.2391 0.1267 0.5037 0.030 Uiso 1 1 calc . . R H63B H 0.2307 0.1423 0.5642 0.030 Uiso 1 1 calc . . R C56 C 0.1492(3) 0.1483(4) 0.3295(2) 0.0291(12) Uani 1 1 d . . . H56 H 0.1111 0.1839 0.3375 0.035 Uiso 1 1 calc . . R C12 C 1.0215(3) 0.8052(4) 0.6226(2) 0.0290(12) Uani 1 1 d . . . H12 H 1.0613 0.8236 0.6554 0.035 Uiso 1 1 calc . . R C10 C 0.9340(3) 0.8490(4) 0.5323(2) 0.0295(12) Uani 1 1 d . . . H10 H 0.9138 0.8973 0.5036 0.035 Uiso 1 1 calc . . R C22 C 0.7419(3) 0.1662(4) 0.3831(2) 0.0240(11) Uani 1 1 d . . . C58 C 0.1870(3) 0.0311(4) 0.2734(2) 0.0289(12) Uani 1 1 d . . . C16 C 0.5585(3) 0.2897(4) 0.6099(2) 0.0255(11) Uani 1 1 d . . . H16 H 0.5445 0.3203 0.5738 0.031 Uiso 1 1 calc . . R C36 C 0.2927(2) 0.3198(3) 0.5881(2) 0.0209(10) Uani 1 1 d . . . C18 C 0.5262(3) 0.2196(4) 0.6854(2) 0.0256(11) Uani 1 1 d . . . C44 C 0.4978(3) 0.8732(4) 0.5909(3) 0.0342(13) Uani 1 1 d . . . C20 C 0.6530(3) 0.2240(4) 0.6913(2) 0.0227(11) Uani 1 1 d . . . H20 H 0.7036 0.2092 0.7112 0.027 Uiso 1 1 calc . . R C17 C 0.5050(3) 0.2655(4) 0.6331(2) 0.0287(12) Uani 1 1 d . . . H17 H 0.4544 0.2801 0.6135 0.034 Uiso 1 1 calc . . R C9 C 0.9072(3) 0.7519(4) 0.5254(2) 0.0252(11) Uani 1 1 d . . . H9 H 0.8687 0.7334 0.4917 0.030 Uiso 1 1 calc . . R C23 C 0.6678(3) 0.1657(4) 0.3497(2) 0.0294(12) Uani 1 1 d . . . H23 H 0.6333 0.2062 0.3594 0.035 Uiso 1 1 calc . . R C57 C 0.1313(3) 0.0829(4) 0.2841(2) 0.0322(12) Uani 1 1 d . . . H57 H 0.0812 0.0740 0.2607 0.039 Uiso 1 1 calc . . R C25 C 0.6948(3) 0.0470(4) 0.2887(2) 0.0267(11) Uani 1 1 d . . . C59 C 0.2602(3) 0.0432(4) 0.3066(2) 0.0326(13) Uani 1 1 d . . . H59 H 0.2980 0.0070 0.2986 0.039 Uiso 1 1 calc . . R C47 C 0.2665(3) 0.2820(4) 0.6345(2) 0.0249(11) Uani 1 1 d . . . H47A H 0.2773 0.2100 0.6411 0.030 Uiso 1 1 calc . . R H47B H 0.2908 0.3187 0.6700 0.030 Uiso 1 1 calc . . R C14 C 0.7582(2) 0.2692(4) 0.6398(2) 0.0228(11) Uani 1 1 d . . . H14A H 0.7628 0.1960 0.6448 0.027 Uiso 1 1 calc . . R H14B H 0.7781 0.3011 0.6774 0.027 Uiso 1 1 calc . . R C54 C 0.3063(3) 0.2241(4) 0.4493(2) 0.0265(11) Uani 1 1 d . . . H54A H 0.3434 0.2471 0.4326 0.032 Uiso 1 1 calc . . R H54B H 0.3194 0.1556 0.4638 0.032 Uiso 1 1 calc . . R C61 C 0.3217(3) 0.4856(4) 0.6375(2) 0.0307(12) Uani 1 1 d . . . H61A H 0.2810 0.4716 0.6522 0.037 Uiso 1 1 calc . . R H61B H 0.3179 0.5565 0.6258 0.037 Uiso 1 1 calc . . R C45 C 0.5257(3) 0.8051(4) 0.6328(2) 0.0340(13) Uani 1 1 d . . . H45 H 0.5647 0.8232 0.6663 0.041 Uiso 1 1 calc . . R C40 C 0.3415(3) 0.5680(4) 0.5350(2) 0.0286(12) Uani 1 1 d . . . H40A H 0.3389 0.5850 0.4962 0.034 Uiso 1 1 calc . . R H40B H 0.3048 0.6092 0.5448 0.034 Uiso 1 1 calc . . R C34 C 0.3248(3) 0.4578(4) 0.5388(2) 0.0245(11) Uani 1 1 d . . . C7 C 0.9316(3) 0.5151(4) 0.5991(2) 0.0265(11) Uani 1 1 d . . . H7A H 0.9327 0.5398 0.6364 0.032 Uiso 1 1 calc . . R H7B H 0.9827 0.4972 0.6017 0.032 Uiso 1 1 calc . . R C30 C 0.8373(3) 0.4577(4) 0.6646(2) 0.0269(11) Uani 1 1 d . . . H30A H 0.7881 0.4514 0.6690 0.032 Uiso 1 1 calc . . R H30B H 0.8444 0.5287 0.6568 0.032 Uiso 1 1 calc . . R C2 C 0.8387(3) 0.3950(4) 0.6151(2) 0.0222(11) Uani 1 1 d . . . C33 C 0.8161(3) 0.0617(4) 0.5765(2) 0.0348(13) Uani 1 1 d . . . H33A H 0.8595 0.0631 0.5644 0.052 Uiso 1 1 calc . . GR H33B H 0.7915 -0.0032 0.5672 0.052 Uiso 1 1 calc . . GR H33C H 0.8317 0.0724 0.6173 0.052 Uiso 1 1 calc . . GR C27 C 0.7922(3) 0.1063(4) 0.3694(2) 0.0317(13) Uani 1 1 d . . . H27 H 0.8428 0.1060 0.3926 0.038 Uiso 1 1 calc . . R C26 C 0.7678(3) 0.0467(4) 0.3214(2) 0.0346(13) Uani 1 1 d . . . H26 H 0.8019 0.0059 0.3114 0.041 Uiso 1 1 calc . . R C28 C 0.9226(3) 0.4033(4) 0.4969(2) 0.0267(11) Uani 1 1 d . . . H28A H 0.9478 0.3457 0.4867 0.032 Uiso 1 1 calc . . R H28B H 0.9610 0.4516 0.5179 0.032 Uiso 1 1 calc . . R C6 C 0.8804(3) 0.3679(3) 0.5344(2) 0.0211(10) Uani 1 1 d . . . C32 C 0.7623(3) 0.1442(3) 0.5462(2) 0.0241(11) Uani 1 1 d . . . H32A H 0.7432 0.1302 0.5052 0.029 Uiso 1 1 calc . . R H32B H 0.7197 0.1452 0.5600 0.029 Uiso 1 1 calc . . R C11 C 0.9902(3) 0.8747(4) 0.5812(2) 0.0269(12) Uani 1 1 d . . . C64 C 0.3308(3) 0.0760(4) 0.5694(2) 0.0378(14) Uani 1 1 d . . . H64A H 0.3551 0.0928 0.6093 0.057 Uiso 1 1 calc . . GR H64B H 0.3665 0.0822 0.5495 0.057 Uiso 1 1 calc . . GR H64C H 0.3124 0.0073 0.5662 0.057 Uiso 1 1 calc . . GR C52 C 0.0223(3) 0.2471(4) 0.6471(2) 0.0273(12) Uani 1 1 d . . . H52 H -0.0296 0.2562 0.6302 0.033 Uiso 1 1 calc . . R C66 C 0.4116(3) 0.4501(5) 0.4476(3) 0.0467(16) Uani 1 1 d . . . H66A H 0.4375 0.3861 0.4574 0.070 Uiso 1 1 calc . . GR H66B H 0.4333 0.4981 0.4781 0.070 Uiso 1 1 calc . . GR H66C H 0.4166 0.4754 0.4126 0.070 Uiso 1 1 calc . . GR C19 C 0.5991(3) 0.1998(4) 0.7147(2) 0.0246(11) Uani 1 1 d . . . H19 H 0.6129 0.1696 0.7508 0.029 Uiso 1 1 calc . . R C24 C 0.6443(3) 0.1064(4) 0.3025(2) 0.0311(12) Uani 1 1 d . . . H24 H 0.5936 0.1061 0.2794 0.037 Uiso 1 1 calc . . R C29 C 0.8714(3) 0.4527(4) 0.4429(2) 0.0344(13) Uani 1 1 d . . . H29A H 0.9008 0.4770 0.4205 0.052 Uiso 1 1 calc . . GR H29B H 0.8455 0.5089 0.4528 0.052 Uiso 1 1 calc . . GR H29C H 0.8351 0.4039 0.4208 0.052 Uiso 1 1 calc . . GR C31 C 0.8976(3) 0.4266(4) 0.7201(2) 0.0362(13) Uani 1 1 d . . . H31A H 0.9464 0.4328 0.7160 0.054 Uiso 1 1 calc . . GR H31B H 0.8895 0.3572 0.7288 0.054 Uiso 1 1 calc . . GR H31C H 0.8952 0.4700 0.7508 0.054 Uiso 1 1 calc . . GR C65 C 0.3307(3) 0.4357(4) 0.4397(2) 0.0303(12) Uani 1 1 d . . . H65A H 0.3085 0.3891 0.4080 0.036 Uiso 1 1 calc . . R H65B H 0.3047 0.5004 0.4298 0.036 Uiso 1 1 calc . . R C39 C 0.3199(3) 0.3947(4) 0.4927(2) 0.0260(11) Uani 1 1 d . . . C62 C 0.3963(4) 0.4685(4) 0.6847(3) 0.0463(16) Uani 1 1 d . . . H62A H 0.4003 0.5131 0.7164 0.070 Uiso 1 1 calc . . GR H62B H 0.4368 0.4824 0.6703 0.070 Uiso 1 1 calc . . GR H62C H 0.3995 0.3991 0.6975 0.070 Uiso 1 1 calc . . GR 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 Br2 0.0335(3) 0.0515(4) 0.0339(3) 0.0020(3) 0.0215(3) -0.0073(3) Br5 0.0481(4) 0.0400(3) 0.0449(4) 0.0057(3) 0.0327(3) -0.0008(3) Br1 0.0305(3) 0.0176(3) 0.0781(5) -0.0054(3) 0.0109(3) -0.0049(2) Br3 0.0403(3) 0.0478(4) 0.0283(3) -0.0088(3) 0.0106(3) -0.0110(3) Br6 0.0438(3) 0.0662(5) 0.0291(3) -0.0168(3) 0.0101(3) -0.0182(3) Br4 0.0332(3) 0.0215(3) 0.1103(6) -0.0142(3) 0.0058(4) -0.0063(2) O5 0.0182(17) 0.038(2) 0.026(2) 0.0110(16) 0.0090(15) 0.0026(15) O2 0.0162(16) 0.034(2) 0.0242(19) 0.0056(15) 0.0087(15) -0.0015(14) O1 0.034(2) 0.0157(18) 0.030(2) 0.0028(15) 0.0084(16) -0.0059(15) O3 0.033(2) 0.030(2) 0.027(2) -0.0052(16) 0.0127(17) 0.0055(16) C4 0.018(2) 0.019(3) 0.023(3) 0.004(2) 0.007(2) 0.0001(19) O4 0.0267(19) 0.0211(19) 0.035(2) 0.0003(16) 0.0057(16) -0.0061(15) C37 0.014(2) 0.016(2) 0.028(3) -0.002(2) 0.005(2) -0.0001(18) O6 0.028(2) 0.030(2) 0.035(2) -0.0076(17) 0.0082(17) 0.0047(16) C41 0.021(2) 0.020(3) 0.027(3) -0.007(2) 0.012(2) -0.001(2) C5 0.022(2) 0.022(3) 0.023(3) -0.004(2) 0.007(2) 0.001(2) C1 0.021(2) 0.023(3) 0.022(3) 0.002(2) 0.005(2) -0.001(2) C3 0.017(2) 0.017(2) 0.028(3) 0.000(2) 0.010(2) 0.0002(18) C48 0.022(2) 0.020(3) 0.024(3) 0.000(2) 0.008(2) -0.002(2) C55 0.030(3) 0.017(3) 0.029(3) -0.001(2) 0.015(2) -0.003(2) C42 0.027(3) 0.018(3) 0.031(3) -0.003(2) 0.005(2) -0.001(2) C8 0.018(2) 0.018(2) 0.027(3) -0.005(2) 0.009(2) -0.0034(19) C50 0.040(3) 0.019(3) 0.023(3) -0.002(2) 0.012(2) -0.003(2) C13 0.027(3) 0.021(3) 0.030(3) 0.003(2) 0.010(2) -0.003(2) C43 0.028(3) 0.020(3) 0.043(3) -0.001(2) 0.005(3) 0.001(2) C60 0.026(3) 0.036(3) 0.034(3) -0.013(3) 0.010(2) -0.006(2) C15 0.023(2) 0.021(3) 0.019(3) -0.001(2) 0.011(2) -0.004(2) C38 0.024(3) 0.023(3) 0.029(3) -0.006(2) 0.010(2) -0.001(2) C53 0.022(3) 0.033(3) 0.022(3) 0.004(2) 0.009(2) 0.005(2) C51 0.038(3) 0.023(3) 0.029(3) -0.004(2) 0.020(3) -0.003(2) C46 0.030(3) 0.026(3) 0.026(3) 0.000(2) 0.008(2) 0.003(2) C35 0.019(2) 0.022(3) 0.028(3) -0.006(2) 0.008(2) 0.003(2) C49 0.030(3) 0.023(3) 0.023(3) 0.001(2) 0.009(2) -0.001(2) C21 0.026(3) 0.020(3) 0.032(3) -0.002(2) 0.011(2) 0.004(2) C63 0.025(3) 0.017(3) 0.030(3) -0.001(2) 0.005(2) -0.005(2) C56 0.025(3) 0.027(3) 0.036(3) 0.011(2) 0.011(2) 0.007(2) C12 0.023(3) 0.031(3) 0.034(3) -0.004(2) 0.012(2) -0.005(2) C10 0.030(3) 0.017(3) 0.041(3) 0.005(2) 0.011(3) -0.001(2) C22 0.025(3) 0.023(3) 0.026(3) 0.001(2) 0.011(2) 0.000(2) C58 0.031(3) 0.037(3) 0.017(3) -0.008(2) 0.005(2) -0.012(2) C16 0.027(3) 0.031(3) 0.020(3) 0.004(2) 0.010(2) 0.001(2) C36 0.018(2) 0.020(3) 0.026(3) -0.002(2) 0.009(2) 0.0008(19) C18 0.030(3) 0.025(3) 0.030(3) -0.007(2) 0.021(2) -0.009(2) C44 0.023(3) 0.018(3) 0.060(4) -0.012(3) 0.013(3) -0.001(2) C20 0.022(2) 0.025(3) 0.022(3) 0.002(2) 0.008(2) -0.003(2) C17 0.022(3) 0.038(3) 0.026(3) -0.001(2) 0.009(2) 0.002(2) C9 0.020(2) 0.024(3) 0.028(3) -0.001(2) 0.003(2) 0.000(2) C23 0.031(3) 0.028(3) 0.029(3) -0.002(2) 0.010(2) 0.006(2) C57 0.026(3) 0.037(3) 0.029(3) 0.005(3) 0.004(2) -0.001(2) C25 0.038(3) 0.025(3) 0.020(3) -0.002(2) 0.013(2) -0.008(2) C59 0.028(3) 0.037(3) 0.035(3) -0.012(3) 0.013(2) -0.005(2) C47 0.019(2) 0.027(3) 0.027(3) -0.006(2) 0.005(2) 0.000(2) C14 0.017(2) 0.028(3) 0.022(3) 0.002(2) 0.004(2) 0.000(2) C54 0.032(3) 0.020(3) 0.030(3) -0.008(2) 0.014(2) -0.006(2) C61 0.037(3) 0.023(3) 0.033(3) -0.005(2) 0.013(3) -0.002(2) C45 0.023(3) 0.038(3) 0.035(3) -0.012(3) 0.002(2) -0.002(2) C40 0.028(3) 0.025(3) 0.030(3) -0.002(2) 0.006(2) -0.003(2) C34 0.024(3) 0.018(3) 0.033(3) -0.003(2) 0.011(2) -0.001(2) C7 0.025(3) 0.030(3) 0.023(3) 0.002(2) 0.005(2) -0.003(2) C30 0.026(3) 0.029(3) 0.027(3) -0.009(2) 0.011(2) -0.003(2) C2 0.024(3) 0.022(3) 0.023(3) -0.005(2) 0.012(2) -0.003(2) C33 0.044(3) 0.022(3) 0.037(3) 0.001(2) 0.012(3) 0.002(2) C27 0.025(3) 0.035(3) 0.037(3) -0.013(3) 0.013(2) -0.004(2) C26 0.024(3) 0.042(3) 0.041(3) -0.010(3) 0.014(3) 0.002(2) C28 0.024(3) 0.027(3) 0.033(3) -0.002(2) 0.014(2) -0.003(2) C6 0.021(2) 0.020(3) 0.023(3) -0.002(2) 0.008(2) 0.003(2) C32 0.024(3) 0.021(3) 0.025(3) 0.000(2) 0.005(2) -0.006(2) C11 0.018(2) 0.018(3) 0.046(3) -0.005(2) 0.013(2) -0.001(2) C64 0.047(3) 0.019(3) 0.040(3) 0.003(2) 0.005(3) 0.003(2) C52 0.023(3) 0.023(3) 0.038(3) -0.001(2) 0.014(2) 0.002(2) C66 0.051(4) 0.047(4) 0.051(4) -0.003(3) 0.029(3) -0.007(3) C19 0.034(3) 0.022(3) 0.020(3) -0.001(2) 0.011(2) -0.003(2) C24 0.029(3) 0.036(3) 0.028(3) 0.010(2) 0.007(2) 0.002(2) C29 0.045(3) 0.038(3) 0.020(3) 0.008(2) 0.011(3) 0.001(3) C31 0.034(3) 0.036(3) 0.033(3) -0.009(3) 0.004(3) -0.003(2) C65 0.032(3) 0.033(3) 0.026(3) -0.002(2) 0.009(2) -0.001(2) C39 0.021(2) 0.029(3) 0.026(3) -0.003(2) 0.004(2) 0.001(2) C62 0.061(4) 0.034(4) 0.037(4) -0.014(3) 0.007(3) -0.008(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 Br2 C18 1.904(4) . ? Br5 C51 1.901(5) . ? Br1 C11 1.909(5) . ? Br3 C25 1.913(5) . ? Br6 C58 1.900(5) . ? Br4 C44 1.915(5) . ? O5 C48 1.370(5) . ? O5 C47 1.441(5) . ? O2 C15 1.370(5) . ? O2 C14 1.448(5) . ? O1 C8 1.370(5) . ? O1 C7 1.418(6) . ? O3 C21 1.458(6) . ? O3 C22 1.380(6) . ? C4 C5 1.400(6) . ? C4 C3 1.405(6) . ? C4 C32 1.527(6) . ? O4 C41 1.368(6) . ? O4 C40 1.446(6) . ? C37 C38 1.406(7) . ? C37 C63 1.516(6) . ? C37 C36 1.408(6) . ? O6 C55 1.364(6) . ? O6 C54 1.431(6) . ? C41 C42 1.383(7) . ? C41 C46 1.393(7) . ? C5 C21 1.510(7) . ? C5 C6 1.404(6) . ? C1 C7 1.529(7) . ? C1 C2 1.402(6) . ? C1 C6 1.410(6) . ? C3 C14 1.500(6) . ? C3 C2 1.404(6) . ? C48 C53 1.402(6) . ? C48 C49 1.390(7) . ? C55 C60 1.387(7) . ? C55 C56 1.382(7) . ? C42 H42 0.9500 . ? C42 C43 1.390(7) . ? C8 C13 1.388(7) . ? C8 C9 1.390(7) . ? C50 H50 0.9500 . ? C50 C51 1.378(7) . ? C50 C49 1.393(6) . ? C13 H13 0.9500 . ? C13 C12 1.398(7) . ? C43 H43 0.9500 . ? C43 C44 1.373(7) . ? C60 H60 0.9500 . ? C60 C59 1.387(7) . ? C15 C16 1.395(7) . ? C15 C20 1.380(6) . ? C38 C54 1.508(6) . ? C38 C39 1.404(7) . ? C53 H53 0.9500 . ? C53 C52 1.381(6) . ? C51 C52 1.385(7) . ? C46 H46 0.9500 . ? C46 C45 1.389(7) . ? C35 C36 1.405(6) . ? C35 C61 1.509(7) . ? C35 C34 1.401(7) . ? C49 H49 0.9500 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C63 C64 1.537(7) . ? C56 H56 0.9500 . ? C56 C57 1.390(7) . ? C12 H12 0.9500 . ? C12 C11 1.376(7) . ? C10 H10 0.9500 . ? C10 C9 1.389(7) . ? C10 C11 1.378(7) . ? C22 C23 1.387(7) . ? C22 C27 1.384(7) . ? C58 C57 1.375(7) . ? C58 C59 1.380(7) . ? C16 H16 0.9500 . ? C16 C17 1.381(6) . ? C36 C47 1.507(6) . ? C18 C17 1.385(7) . ? C18 C19 1.369(7) . ? C44 C45 1.362(8) . ? C20 H20 0.9500 . ? C20 C19 1.390(6) . ? C17 H17 0.9500 . ? C9 H9 0.9500 . ? C23 H23 0.9500 . ? C23 C24 1.373(7) . ? C57 H57 0.9500 . ? C25 C26 1.363(7) . ? C25 C24 1.386(7) . ? C59 H59 0.9500 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C61 C62 1.539(8) . ? C45 H45 0.9500 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C40 C34 1.523(7) . ? C34 C39 1.413(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 C2 1.514(6) . ? C30 C31 1.541(7) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C33 C32 1.529(7) . ? C27 H27 0.9500 . ? C27 C26 1.393(7) . ? C26 H26 0.9500 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C6 1.514(6) . ? C28 C29 1.534(7) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C52 H52 0.9500 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C66 C65 1.509(7) . ? C19 H19 0.9500 . ? C24 H24 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C65 C39 1.524(7) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? 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 C48 O5 C47 119.2(4) . . ? C15 O2 C14 116.7(3) . . ? C8 O1 C7 117.5(4) . . ? C22 O3 C21 117.2(4) . . ? C5 C4 C3 119.4(4) . . ? C5 C4 C32 120.3(4) . . ? C3 C4 C32 120.2(4) . . ? C41 O4 C40 116.6(4) . . ? C38 C37 C63 119.3(4) . . ? C38 C37 C36 119.4(4) . . ? C36 C37 C63 121.2(4) . . ? C55 O6 C54 116.6(4) . . ? O4 C41 C42 124.2(4) . . ? O4 C41 C46 115.9(4) . . ? C42 C41 C46 119.9(5) . . ? C4 C5 C21 118.4(4) . . ? C4 C5 C6 120.5(4) . . ? C6 C5 C21 121.1(4) . . ? C2 C1 C7 119.6(4) . . ? C2 C1 C6 121.1(4) . . ? C6 C1 C7 119.2(4) . . ? C4 C3 C14 119.7(4) . . ? C2 C3 C4 121.1(4) . . ? C2 C3 C14 119.2(4) . . ? O5 C48 C53 114.8(4) . . ? O5 C48 C49 124.9(4) . . ? C49 C48 C53 120.3(4) . . ? O6 C55 C60 124.2(5) . . ? O6 C55 C56 115.8(4) . . ? C56 C55 C60 120.0(5) . . ? C41 C42 H42 120.1 . . ? C41 C42 C43 119.9(5) . . ? C43 C42 H42 120.1 . . ? O1 C8 C13 124.7(4) . . ? O1 C8 C9 115.0(4) . . ? C13 C8 C9 120.3(4) . . ? C51 C50 H50 120.0 . . ? C51 C50 C49 119.9(5) . . ? C49 C50 H50 120.0 . . ? C8 C13 H13 120.4 . . ? C8 C13 C12 119.2(5) . . ? C12 C13 H13 120.4 . . ? C42 C43 H43 120.3 . . ? C44 C43 C42 119.4(5) . . ? C44 C43 H43 120.3 . . ? C55 C60 H60 119.9 . . ? C59 C60 C55 120.1(5) . . ? C59 C60 H60 119.9 . . ? O2 C15 C16 115.6(4) . . ? O2 C15 C20 124.6(4) . . ? C20 C15 C16 119.8(4) . . ? C37 C38 C54 120.4(4) . . ? C39 C38 C37 120.5(4) . . ? C39 C38 C54 119.1(4) . . ? C48 C53 H53 120.2 . . ? C52 C53 C48 119.7(5) . . ? C52 C53 H53 120.2 . . ? C50 C51 Br5 120.4(4) . . ? C50 C51 C52 121.1(5) . . ? C52 C51 Br5 118.5(4) . . ? C41 C46 H46 120.2 . . ? C45 C46 C41 119.6(5) . . ? C45 C46 H46 120.2 . . ? C36 C35 C61 119.4(4) . . ? C34 C35 C36 119.4(4) . . ? C34 C35 C61 121.2(4) . . ? C48 C49 C50 119.3(5) . . ? C48 C49 H49 120.3 . . ? C50 C49 H49 120.3 . . ? O3 C21 C5 107.8(4) . . ? O3 C21 H21A 110.1 . . ? O3 C21 H21B 110.1 . . ? C5 C21 H21A 110.1 . . ? C5 C21 H21B 110.1 . . ? H21A C21 H21B 108.5 . . ? C37 C63 H63A 108.9 . . ? C37 C63 H63B 108.9 . . ? C37 C63 C64 113.2(4) . . ? H63A C63 H63B 107.7 . . ? C64 C63 H63A 108.9 . . ? C64 C63 H63B 108.9 . . ? C55 C56 H56 119.9 . . ? C55 C56 C57 120.1(5) . . ? C57 C56 H56 119.9 . . ? C13 C12 H12 120.1 . . ? C11 C12 C13 119.9(5) . . ? C11 C12 H12 120.1 . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C11 C10 C9 119.4(5) . . ? O3 C22 C23 116.1(4) . . ? O3 C22 C27 123.7(4) . . ? C27 C22 C23 120.3(5) . . ? C57 C58 Br6 119.6(4) . . ? C57 C58 C59 121.4(5) . . ? C59 C58 Br6 119.0(4) . . ? C15 C16 H16 119.9 . . ? C17 C16 C15 120.2(5) . . ? C17 C16 H16 119.9 . . ? C37 C36 C47 118.7(4) . . ? C35 C36 C37 120.5(4) . . ? C35 C36 C47 120.5(4) . . ? C17 C18 Br2 120.3(4) . . ? C19 C18 Br2 118.6(4) . . ? C19 C18 C17 121.1(4) . . ? C43 C44 Br4 118.6(4) . . ? C45 C44 Br4 119.8(4) . . ? C45 C44 C43 121.5(5) . . ? C15 C20 H20 120.1 . . ? C15 C20 C19 119.8(4) . . ? C19 C20 H20 120.1 . . ? C16 C17 C18 119.2(5) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C8 C9 H9 120.0 . . ? C10 C9 C8 119.9(5) . . ? C10 C9 H9 120.0 . . ? C22 C23 H23 120.1 . . ? C24 C23 C22 119.8(5) . . ? C24 C23 H23 120.1 . . ? C56 C57 H57 120.4 . . ? C58 C57 C56 119.2(5) . . ? C58 C57 H57 120.4 . . ? C26 C25 Br3 119.5(4) . . ? C26 C25 C24 120.9(5) . . ? C24 C25 Br3 119.6(4) . . ? C60 C59 H59 120.4 . . ? C58 C59 C60 119.2(5) . . ? C58 C59 H59 120.4 . . ? O5 C47 C36 104.8(4) . . ? O5 C47 H47A 110.8 . . ? O5 C47 H47B 110.8 . . ? C36 C47 H47A 110.8 . . ? C36 C47 H47B 110.8 . . ? H47A C47 H47B 108.9 . . ? O2 C14 C3 107.2(4) . . ? O2 C14 H14A 110.3 . . ? O2 C14 H14B 110.3 . . ? C3 C14 H14A 110.3 . . ? C3 C14 H14B 110.3 . . ? H14A C14 H14B 108.5 . . ? O6 C54 C38 108.3(4) . . ? O6 C54 H54A 110.0 . . ? O6 C54 H54B 110.0 . . ? C38 C54 H54A 110.0 . . ? C38 C54 H54B 110.0 . . ? H54A C54 H54B 108.4 . . ? C35 C61 H61A 109.2 . . ? C35 C61 H61B 109.2 . . ? C35 C61 C62 112.1(4) . . ? H61A C61 H61B 107.9 . . ? C62 C61 H61A 109.2 . . ? C62 C61 H61B 109.2 . . ? C46 C45 H45 120.1 . . ? C44 C45 C46 119.7(5) . . ? C44 C45 H45 120.1 . . ? O4 C40 H40A 110.1 . . ? O4 C40 H40B 110.1 . . ? O4 C40 C34 107.9(4) . . ? H40A C40 H40B 108.4 . . ? C34 C40 H40A 110.1 . . ? C34 C40 H40B 110.1 . . ? C35 C34 C40 120.1(4) . . ? C35 C34 C39 120.7(4) . . ? C39 C34 C40 119.1(4) . . ? O1 C7 C1 108.3(4) . . ? O1 C7 H7A 110.0 . . ? O1 C7 H7B 110.0 . . ? C1 C7 H7A 110.0 . . ? C1 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? H30A C30 H30B 107.9 . . ? C2 C30 H30A 109.1 . . ? C2 C30 H30B 109.1 . . ? C2 C30 C31 112.3(4) . . ? C31 C30 H30A 109.1 . . ? C31 C30 H30B 109.1 . . ? C1 C2 C3 118.5(4) . . ? C1 C2 C30 120.9(4) . . ? C3 C2 C30 120.6(4) . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? C22 C27 H27 120.3 . . ? C22 C27 C26 119.4(5) . . ? C26 C27 H27 120.3 . . ? C25 C26 C27 119.8(5) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? H28A C28 H28B 107.9 . . ? C6 C28 H28A 109.2 . . ? C6 C28 H28B 109.2 . . ? C6 C28 C29 111.9(4) . . ? C29 C28 H28A 109.2 . . ? C29 C28 H28B 109.2 . . ? C5 C6 C1 119.1(4) . . ? C5 C6 C28 120.2(4) . . ? C1 C6 C28 120.7(4) . . ? C4 C32 C33 110.9(4) . . ? C4 C32 H32A 109.5 . . ? C4 C32 H32B 109.5 . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 108.0 . . ? C12 C11 Br1 119.4(4) . . ? C12 C11 C10 121.2(5) . . ? C10 C11 Br1 119.4(4) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C53 C52 C51 119.7(5) . . ? C53 C52 H52 120.2 . . ? C51 C52 H52 120.2 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? C18 C19 C20 119.9(4) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C23 C24 C25 119.8(5) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C66 C65 H65A 109.3 . . ? C66 C65 H65B 109.3 . . ? C66 C65 C39 111.7(4) . . ? H65A C65 H65B 107.9 . . ? C39 C65 H65A 109.3 . . ? C39 C65 H65B 109.3 . . ? C38 C39 C34 119.1(4) . . ? C38 C39 C65 120.0(4) . . ? C34 C39 C65 120.9(4) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 -177.3(4) . . . . ? Br2 C18 C19 C20 177.2(4) . . . . ? Br5 C51 C52 C53 -179.5(4) . . . . ? Br3 C25 C26 C27 178.2(4) . . . . ? Br3 C25 C24 C23 -178.1(4) . . . . ? Br6 C58 C57 C56 179.6(4) . . . . ? Br6 C58 C59 C60 -179.9(4) . . . . ? Br4 C44 C45 C46 178.1(4) . . . . ? O5 C48 C53 C52 179.3(4) . . . . ? O5 C48 C49 C50 -179.2(4) . . . . ? O2 C15 C16 C17 -179.9(4) . . . . ? O2 C15 C20 C19 179.8(4) . . . . ? O1 C8 C13 C12 -177.0(4) . . . . ? O1 C8 C9 C10 176.8(4) . . . . ? O3 C22 C23 C24 179.1(4) . . . . ? O3 C22 C27 C26 -179.0(5) . . . . ? C4 C5 C21 O3 72.2(5) . . . . ? C4 C5 C6 C1 -1.9(7) . . . . ? C4 C5 C6 C28 179.1(4) . . . . ? C4 C3 C14 O2 -82.5(5) . . . . ? C4 C3 C2 C1 -3.3(7) . . . . ? C4 C3 C2 C30 179.5(4) . . . . ? O4 C41 C42 C43 -179.7(4) . . . . ? O4 C41 C46 C45 179.7(4) . . . . ? O4 C40 C34 C35 70.7(5) . . . . ? O4 C40 C34 C39 -110.8(5) . . . . ? C37 C38 C54 O6 91.6(5) . . . . ? C37 C38 C39 C34 6.5(7) . . . . ? C37 C38 C39 C65 -174.5(4) . . . . ? C37 C36 C47 O5 -85.8(5) . . . . ? O6 C55 C60 C59 177.6(5) . . . . ? O6 C55 C56 C57 -178.2(4) . . . . ? C41 O4 C40 C34 -179.6(4) . . . . ? C41 C42 C43 C44 -0.4(8) . . . . ? C41 C46 C45 C44 0.4(7) . . . . ? C5 C4 C3 C14 179.2(4) . . . . ? C5 C4 C3 C2 -1.5(7) . . . . ? C5 C4 C32 C33 87.1(5) . . . . ? C3 C4 C5 C21 -176.9(4) . . . . ? C3 C4 C5 C6 4.2(7) . . . . ? C3 C4 C32 C33 -90.2(5) . . . . ? C48 O5 C47 C36 174.4(4) . . . . ? C48 C53 C52 C51 0.7(7) . . . . ? C55 O6 C54 C38 -175.5(4) . . . . ? C55 C60 C59 C58 0.1(8) . . . . ? C55 C56 C57 C58 0.7(8) . . . . ? C42 C41 C46 C45 -0.1(7) . . . . ? C42 C43 C44 Br4 -178.1(4) . . . . ? C42 C43 C44 C45 0.8(8) . . . . ? C8 O1 C7 C1 173.9(4) . . . . ? C8 C13 C12 C11 0.2(7) . . . . ? C50 C51 C52 C53 -0.8(8) . . . . ? C13 C8 C9 C10 -2.3(7) . . . . ? C13 C12 C11 Br1 176.5(4) . . . . ? C13 C12 C11 C10 -2.1(7) . . . . ? C43 C44 C45 C46 -0.7(8) . . . . ? C60 C55 C56 C57 -0.5(8) . . . . ? C15 O2 C14 C3 178.8(4) . . . . ? C15 C16 C17 C18 -0.9(8) . . . . ? C15 C20 C19 C18 1.2(7) . . . . ? C38 C37 C63 C64 90.7(6) . . . . ? C38 C37 C36 C35 -0.6(7) . . . . ? C38 C37 C36 C47 173.0(4) . . . . ? C53 C48 C49 C50 0.9(7) . . . . ? C51 C50 C49 C48 -1.0(7) . . . . ? C46 C41 C42 C43 0.1(7) . . . . ? C35 C36 C47 O5 87.8(5) . . . . ? C35 C34 C39 C38 -2.6(7) . . . . ? C35 C34 C39 C65 178.3(4) . . . . ? C49 C48 C53 C52 -0.8(7) . . . . ? C49 C50 C51 Br5 179.6(4) . . . . ? C49 C50 C51 C52 1.0(7) . . . . ? C21 O3 C22 C23 169.1(4) . . . . ? C21 O3 C22 C27 -11.0(7) . . . . ? C21 C5 C6 C1 179.2(4) . . . . ? C21 C5 C6 C28 0.3(7) . . . . ? C63 C37 C38 C54 -5.2(7) . . . . ? C63 C37 C38 C39 172.8(4) . . . . ? C63 C37 C36 C35 -178.3(4) . . . . ? C63 C37 C36 C47 -4.6(7) . . . . ? C56 C55 C60 C59 0.2(8) . . . . ? C22 O3 C21 C5 -169.9(4) . . . . ? C22 C23 C24 C25 0.4(8) . . . . ? C22 C27 C26 C25 -0.7(8) . . . . ? C16 C15 C20 C19 -0.8(7) . . . . ? C36 C37 C38 C54 177.1(4) . . . . ? C36 C37 C38 C39 -4.8(7) . . . . ? C36 C37 C63 C64 -91.7(5) . . . . ? C36 C35 C61 C62 79.1(6) . . . . ? C36 C35 C34 C40 175.8(4) . . . . ? C36 C35 C34 C39 -2.7(7) . . . . ? C20 C15 C16 C17 0.7(7) . . . . ? C17 C18 C19 C20 -1.4(7) . . . . ? C9 C8 C13 C12 2.0(7) . . . . ? C9 C10 C11 Br1 -176.9(4) . . . . ? C9 C10 C11 C12 1.8(7) . . . . ? C23 C22 C27 C26 0.9(8) . . . . ? C57 C58 C59 C60 0.1(8) . . . . ? C59 C58 C57 C56 -0.4(8) . . . . ? C47 O5 C48 C53 -175.7(4) . . . . ? C47 O5 C48 C49 4.4(7) . . . . ? C14 O2 C15 C16 -175.1(4) . . . . ? C14 O2 C15 C20 4.3(7) . . . . ? C14 C3 C2 C1 176.0(4) . . . . ? C14 C3 C2 C30 -1.2(7) . . . . ? C54 O6 C55 C60 -10.3(7) . . . . ? C54 O6 C55 C56 167.2(4) . . . . ? C54 C38 C39 C34 -175.5(4) . . . . ? C54 C38 C39 C65 3.6(7) . . . . ? C61 C35 C36 C37 -175.3(4) . . . . ? C61 C35 C36 C47 11.2(7) . . . . ? C61 C35 C34 C40 -4.6(7) . . . . ? C61 C35 C34 C39 176.9(4) . . . . ? C40 O4 C41 C42 -22.0(6) . . . . ? C40 O4 C41 C46 158.2(4) . . . . ? C40 C34 C39 C38 178.8(4) . . . . ? C40 C34 C39 C65 -0.3(7) . . . . ? C34 C35 C36 C37 4.4(7) . . . . ? C34 C35 C36 C47 -169.1(4) . . . . ? C34 C35 C61 C62 -100.6(6) . . . . ? C7 O1 C8 C13 -1.5(6) . . . . ? C7 O1 C8 C9 179.4(4) . . . . ? C7 C1 C2 C3 -172.4(4) . . . . ? C7 C1 C2 C30 4.8(7) . . . . ? C7 C1 C6 C5 175.0(4) . . . . ? C7 C1 C6 C28 -6.1(7) . . . . ? C2 C1 C7 O1 -113.0(5) . . . . ? C2 C1 C6 C5 -3.0(7) . . . . ? C2 C1 C6 C28 175.9(4) . . . . ? C2 C3 C14 O2 98.2(5) . . . . ? C27 C22 C23 C24 -0.7(8) . . . . ? C26 C25 C24 C23 -0.2(8) . . . . ? C6 C5 C21 O3 -108.8(5) . . . . ? C6 C1 C7 O1 69.0(5) . . . . ? C6 C1 C2 C3 5.6(7) . . . . ? C6 C1 C2 C30 -177.2(4) . . . . ? C32 C4 C5 C21 5.8(7) . . . . ? C32 C4 C5 C6 -173.1(4) . . . . ? C32 C4 C3 C14 -3.5(7) . . . . ? C32 C4 C3 C2 175.8(4) . . . . ? C11 C10 C9 C8 0.4(7) . . . . ? C66 C65 C39 C38 -100.3(6) . . . . ? C66 C65 C39 C34 78.8(6) . . . . ? C19 C18 C17 C16 1.2(8) . . . . ? C24 C25 C26 C27 0.3(8) . . . . ? C29 C28 C6 C5 77.6(6) . . . . ? C29 C28 C6 C1 -101.3(5) . . . . ? C31 C30 C2 C1 -90.5(6) . . . . ? C31 C30 C2 C3 86.6(6) . . . . ? C39 C38 C54 O6 -86.5(5) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962412' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-gf-190K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-gf, 190 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Br3 O3' _chemical_formula_sum 'C33 H33 Br3 O3' _chemical_formula_weight 717.32 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 19.2260(7) _cell_length_b 13.4255(5) _cell_length_c 25.2443(13) _cell_angle_alpha 90.00 _cell_angle_beta 109.776(5) _cell_angle_gamma 90.00 _cell_volume 6131.7(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4390 _cell_measurement_temperature 190(2) _cell_measurement_theta_max 29.0943 _cell_measurement_theta_min 3.4792 _exptl_absorpt_coefficient_mu 3.979 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.51967 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2880 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_unetI/netI 0.1062 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 38242 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.16 _diffrn_reflns_theta_min 3.49 _diffrn_ambient_temperature 190(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.866 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0294574000 _diffrn_orient_matrix_UB_12 -0.0332516000 _diffrn_orient_matrix_UB_13 -0.0131901000 _diffrn_orient_matrix_UB_21 0.0016259000 _diffrn_orient_matrix_UB_22 0.0135387000 _diffrn_orient_matrix_UB_23 -0.0267108000 _diffrn_orient_matrix_UB_31 0.0258231000 _diffrn_orient_matrix_UB_32 -0.0387662000 _diffrn_orient_matrix_UB_33 0.0019802000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 7843 _reflns_number_total 14340 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 2.266 _refine_diff_density_min -0.945 _refine_diff_density_rms 0.117 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 14340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1484 _refine_ls_R_factor_gt 0.0680 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0766P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1404 _refine_ls_wR_factor_ref 0.1754 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C63(H63A,H63B), C47(H47A,H47B), C14(H14A,H14B), C54(H54A, H54B), C61(H61A,H61B), C40(H40A,H40B), C7(H7A,H7B), C30(H30A,H30B), C28(H28A, H28B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C42(H42), C50(H50), C13(H13), C43(H43), C60(H60), C53(H53), C46(H46), C49(H49), C56(H56), C12(H12), C10(H10), C16(H16), C20(H20), C17(H17), C9(H9), C23(H23), C57(H57), C59(H59), C45(H45), C27(H27), C26(H26), C52(H52), C19(H19), C24(H24) 2.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C29(H29A,H29B, H29C), C31(H31A,H31B,H31C), C62(H62A,H62B,H62C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.45483(3) 0.17976(5) 0.71687(3) 0.04623(19) Uani 1 1 d . . . Br5 Br -0.01580(4) 0.15612(5) 0.73447(3) 0.0500(2) Uani 1 1 d . . . Br1 Br 1.02386(3) 1.00831(4) 0.59254(3) 0.0541(2) Uani 1 1 d . . . Br3 Br 0.66221(3) -0.03163(5) 0.22208(3) 0.04895(19) Uani 1 1 d . . . Br6 Br 0.16276(4) -0.05710(6) 0.21219(3) 0.0577(2) Uani 1 1 d . . . Br4 Br 0.53491(4) 1.00522(5) 0.60055(4) 0.0745(3) Uani 1 1 d . . . O5 O 0.18781(18) 0.2989(3) 0.61427(16) 0.0330(9) Uani 1 1 d . . . O2 O 0.68177(17) 0.2966(3) 0.61220(16) 0.0315(9) Uani 1 1 d . . . O1 O 0.90348(19) 0.5897(3) 0.55820(16) 0.0350(9) Uani 1 1 d . . . O3 O 0.7614(2) 0.2294(3) 0.42925(16) 0.0351(9) Uani 1 1 d . . . C4 C 0.8003(2) 0.2459(4) 0.5560(2) 0.0228(11) Uani 1 1 d . . . O4 O 0.41508(19) 0.5861(3) 0.57468(16) 0.0358(9) Uani 1 1 d . . . C37 C 0.2895(3) 0.2548(4) 0.5437(2) 0.0268(12) Uani 1 1 d . . . O6 O 0.23460(19) 0.2248(3) 0.40831(17) 0.0404(10) Uani 1 1 d . . . C41 C 0.4396(3) 0.6822(4) 0.5772(2) 0.0268(12) Uani 1 1 d . . . C5 C 0.8384(3) 0.2799(4) 0.5214(2) 0.0274(12) Uani 1 1 d . . . C1 C 0.8810(3) 0.4236(4) 0.5821(2) 0.0285(12) Uani 1 1 d . . . C3 C 0.8002(2) 0.3047(4) 0.6023(2) 0.0242(11) Uani 1 1 d . . . C48 C 0.1462(3) 0.2644(4) 0.6451(2) 0.0263(12) Uani 1 1 d . . . C55 C 0.2229(3) 0.1611(4) 0.3639(2) 0.0298(12) Uani 1 1 d . . . C42 C 0.4136(3) 0.7521(4) 0.5357(3) 0.0348(14) Uani 1 1 d . . . H42 H 0.3752 0.7346 0.5018 0.042 Uiso 1 1 calc . . R C8 C 0.9368(3) 0.6817(4) 0.5685(2) 0.0256(12) Uani 1 1 d . . . C50 C 0.1258(3) 0.1863(4) 0.7239(2) 0.0336(13) Uani 1 1 d . . . H50 H 0.1444 0.1541 0.7594 0.040 Uiso 1 1 calc . . R C13 C 0.9946(3) 0.7071(4) 0.6159(2) 0.0315(13) Uani 1 1 d . . . H13 H 1.0162 0.6584 0.6439 0.038 Uiso 1 1 calc . . R C43 C 0.4419(3) 0.8472(4) 0.5420(3) 0.0400(15) Uani 1 1 d . . . H43 H 0.4232 0.8949 0.5128 0.048 Uiso 1 1 calc . . R C60 C 0.2771(3) 0.1093(4) 0.3518(3) 0.0386(15) Uani 1 1 d . . . H60 H 0.3273 0.1179 0.3748 0.046 Uiso 1 1 calc . . R C15 C 0.6333(3) 0.2689(4) 0.6388(2) 0.0245(11) Uani 1 1 d . . . C38 C 0.3069(3) 0.2918(4) 0.4976(2) 0.0299(13) Uani 1 1 d . . . C53 C 0.0701(3) 0.2798(4) 0.6201(2) 0.0339(13) Uani 1 1 d . . . H53 H 0.0510 0.3126 0.5847 0.041 Uiso 1 1 calc . . R C51 C 0.0516(3) 0.2009(4) 0.6991(2) 0.0314(13) Uani 1 1 d . . . C46 C 0.4967(3) 0.7084(4) 0.6263(2) 0.0343(14) Uani 1 1 d . . . H46 H 0.5160 0.6602 0.6551 0.041 Uiso 1 1 calc . . R C35 C 0.3123(3) 0.4190(4) 0.5870(2) 0.0281(12) Uani 1 1 d . . . C49 C 0.1742(3) 0.2185(4) 0.6971(2) 0.0296(12) Uani 1 1 d . . . H49 H 0.2260 0.2091 0.7143 0.035 Uiso 1 1 calc . . R C21 C 0.8350(3) 0.2183(4) 0.4705(2) 0.0323(13) Uani 1 1 d . . . H21A H 0.8726 0.2417 0.4546 0.039 Uiso 1 1 calc . . R H21B H 0.8449 0.1475 0.4812 0.039 Uiso 1 1 calc . . R C63 C 0.2655(3) 0.1467(4) 0.5433(2) 0.0303(13) Uani 1 1 d . . . H63A H 0.2389 0.1262 0.5040 0.036 Uiso 1 1 calc . . R H63B H 0.2306 0.1414 0.5644 0.036 Uiso 1 1 calc . . R C56 C 0.1492(3) 0.1484(4) 0.3306(2) 0.0355(14) Uani 1 1 d . . . H56 H 0.1112 0.1832 0.3391 0.043 Uiso 1 1 calc . . R C12 C 1.0214(3) 0.8042(4) 0.6230(2) 0.0334(13) Uani 1 1 d . . . H12 H 1.0608 0.8224 0.6560 0.040 Uiso 1 1 calc . . R C10 C 0.9344(3) 0.8477(4) 0.5327(3) 0.0385(15) Uani 1 1 d . . . H10 H 0.9145 0.8956 0.5038 0.046 Uiso 1 1 calc . . R C22 C 0.7419(3) 0.1675(4) 0.3829(2) 0.0306(13) Uani 1 1 d . . . C58 C 0.1867(3) 0.0325(4) 0.2738(2) 0.0332(13) Uani 1 1 d . . . C16 C 0.5592(3) 0.2899(4) 0.6100(2) 0.0317(13) Uani 1 1 d . . . H16 H 0.5452 0.3209 0.5741 0.038 Uiso 1 1 calc . . R C36 C 0.2920(2) 0.3192(4) 0.5884(2) 0.0231(11) Uani 1 1 d . . . C18 C 0.5268(3) 0.2198(4) 0.6850(2) 0.0311(13) Uani 1 1 d . . . C44 C 0.4975(3) 0.8726(4) 0.5912(3) 0.0415(16) Uani 1 1 d . . . C20 C 0.6540(3) 0.2238(4) 0.6907(2) 0.0270(12) Uani 1 1 d . . . H20 H 0.7045 0.2093 0.7106 0.032 Uiso 1 1 calc . . R C17 C 0.5061(3) 0.2657(4) 0.6334(2) 0.0337(13) Uani 1 1 d . . . H17 H 0.4555 0.2807 0.6139 0.040 Uiso 1 1 calc . . R C9 C 0.9076(3) 0.7510(4) 0.5262(3) 0.0327(13) Uani 1 1 d . . . H9 H 0.8691 0.7322 0.4926 0.039 Uiso 1 1 calc . . R C23 C 0.6683(3) 0.1670(4) 0.3497(2) 0.0353(14) Uani 1 1 d . . . H23 H 0.6342 0.2082 0.3593 0.042 Uiso 1 1 calc . . R C57 C 0.1317(3) 0.0842(4) 0.2848(3) 0.0386(15) Uani 1 1 d . . . H57 H 0.0817 0.0761 0.2612 0.046 Uiso 1 1 calc . . R C25 C 0.6943(3) 0.0477(4) 0.2890(2) 0.0323(13) Uani 1 1 d . . . C59 C 0.2596(3) 0.0450(4) 0.3067(3) 0.0394(15) Uani 1 1 d . . . H59 H 0.2975 0.0096 0.2984 0.047 Uiso 1 1 calc . . R C47 C 0.2663(3) 0.2814(4) 0.6345(2) 0.0297(13) Uani 1 1 d . . . H47A H 0.2772 0.2095 0.6412 0.036 Uiso 1 1 calc . . R H47B H 0.2905 0.3182 0.6700 0.036 Uiso 1 1 calc . . R C14 C 0.7581(2) 0.2695(4) 0.6390(2) 0.0287(12) Uani 1 1 d . . . H14A H 0.7628 0.1964 0.6438 0.034 Uiso 1 1 calc . . R H14B H 0.7780 0.3010 0.6766 0.034 Uiso 1 1 calc . . R C54 C 0.3065(3) 0.2244(4) 0.4497(2) 0.0340(14) Uani 1 1 d . . . H54A H 0.3432 0.2481 0.4329 0.041 Uiso 1 1 calc . . R H54B H 0.3201 0.1558 0.4638 0.041 Uiso 1 1 calc . . R C61 C 0.3215(3) 0.4849(4) 0.6379(3) 0.0390(15) Uani 1 1 d . . . H61A H 0.2808 0.4711 0.6527 0.047 Uiso 1 1 calc . . R H61B H 0.3177 0.5556 0.6261 0.047 Uiso 1 1 calc . . R C45 C 0.5254(3) 0.8034(4) 0.6333(3) 0.0402(15) Uani 1 1 d . . . H45 H 0.5641 0.8210 0.6669 0.048 Uiso 1 1 calc . . R C40 C 0.3416(3) 0.5672(4) 0.5355(3) 0.0359(14) Uani 1 1 d . . . H40A H 0.3390 0.5844 0.4968 0.043 Uiso 1 1 calc . . R H40B H 0.3049 0.6079 0.5454 0.043 Uiso 1 1 calc . . R C34 C 0.3258(3) 0.4573(4) 0.5393(2) 0.0300(12) Uani 1 1 d . . . C7 C 0.9311(3) 0.5144(4) 0.5992(2) 0.0332(13) Uani 1 1 d . . . H7A H 0.9320 0.5388 0.6365 0.040 Uiso 1 1 calc . . R H7B H 0.9821 0.4965 0.6020 0.040 Uiso 1 1 calc . . R C30 C 0.8370(3) 0.4571(4) 0.6640(2) 0.0346(13) Uani 1 1 d . . . H30A H 0.7881 0.4499 0.6686 0.041 Uiso 1 1 calc . . R H30B H 0.8435 0.5282 0.6563 0.041 Uiso 1 1 calc . . R C2 C 0.8385(3) 0.3953(4) 0.6146(2) 0.0251(12) Uani 1 1 d . . . C33 C 0.8164(3) 0.0628(4) 0.5760(3) 0.0437(16) Uani 1 1 d . . . H33A H 0.8586 0.0627 0.5625 0.066 Uiso 1 1 calc . . GR H33B H 0.7913 -0.0018 0.5679 0.066 Uiso 1 1 calc . . GR H33C H 0.8340 0.0747 0.6167 0.066 Uiso 1 1 calc . . GR C27 C 0.7914(3) 0.1059(4) 0.3690(3) 0.0402(15) Uani 1 1 d . . . H27 H 0.8419 0.1046 0.3923 0.048 Uiso 1 1 calc . . R C26 C 0.7677(3) 0.0470(4) 0.3217(3) 0.0407(15) Uani 1 1 d . . . H26 H 0.8017 0.0062 0.3118 0.049 Uiso 1 1 calc . . R C28 C 0.9224(3) 0.4035(4) 0.4967(2) 0.0342(14) Uani 1 1 d . . . H28A H 0.9607 0.4517 0.5179 0.041 Uiso 1 1 calc . . R H28B H 0.9478 0.3461 0.4866 0.041 Uiso 1 1 calc . . R C6 C 0.8798(3) 0.3674(4) 0.5344(2) 0.0259(12) Uani 1 1 d . . . C32 C 0.7623(3) 0.1454(4) 0.5461(2) 0.0291(12) Uani 1 1 d . . . H32A H 0.7425 0.1315 0.5052 0.035 Uiso 1 1 calc . . R H32B H 0.7202 0.1465 0.5604 0.035 Uiso 1 1 calc . . R C11 C 0.9904(3) 0.8737(4) 0.5819(3) 0.0327(14) Uani 1 1 d . . . C64 C 0.3299(3) 0.0756(4) 0.5691(3) 0.0489(17) Uani 1 1 d . . . H64A H 0.3552 0.0936 0.6086 0.073 Uiso 1 1 calc . . GR H64B H 0.3646 0.0802 0.5484 0.073 Uiso 1 1 calc . . GR H64C H 0.3112 0.0073 0.5670 0.073 Uiso 1 1 calc . . GR C52 C 0.0230(3) 0.2468(4) 0.6472(3) 0.0357(14) Uani 1 1 d . . . H52 H -0.0289 0.2555 0.6303 0.043 Uiso 1 1 calc . . R C66 C 0.4111(3) 0.4479(5) 0.4481(3) 0.060(2) Uani 1 1 d . . . H66A H 0.4356 0.3828 0.4552 0.091 Uiso 1 1 calc . . GR H66B H 0.4335 0.4916 0.4805 0.091 Uiso 1 1 calc . . GR H66C H 0.4170 0.4777 0.4144 0.091 Uiso 1 1 calc . . GR C19 C 0.6001(3) 0.1995(4) 0.7138(2) 0.0308(13) Uani 1 1 d . . . H19 H 0.6139 0.1687 0.7497 0.037 Uiso 1 1 calc . . R C24 C 0.6438(3) 0.1067(4) 0.3023(3) 0.0404(15) Uani 1 1 d . . . H24 H 0.5931 0.1060 0.2794 0.048 Uiso 1 1 calc . . R C29 C 0.8724(3) 0.4525(5) 0.4434(3) 0.0446(16) Uani 1 1 d . . . H29A H 0.9021 0.4756 0.4209 0.067 Uiso 1 1 calc . . GR H29B H 0.8472 0.5094 0.4531 0.067 Uiso 1 1 calc . . GR H29C H 0.8357 0.4042 0.4215 0.067 Uiso 1 1 calc . . GR C31 C 0.8972(3) 0.4268(4) 0.7188(3) 0.0433(16) Uani 1 1 d . . . H31A H 0.9458 0.4371 0.7152 0.065 Uiso 1 1 calc . . GR H31B H 0.8913 0.3563 0.7265 0.065 Uiso 1 1 calc . . GR H31C H 0.8930 0.4675 0.7498 0.065 Uiso 1 1 calc . . GR C65 C 0.3316(3) 0.4353(5) 0.4393(3) 0.0422(15) Uani 1 1 d . . . H65A H 0.3094 0.3889 0.4076 0.051 Uiso 1 1 calc . . R H65B H 0.3062 0.5003 0.4294 0.051 Uiso 1 1 calc . . R C39 C 0.3206(3) 0.3940(4) 0.4932(2) 0.0306(13) Uani 1 1 d . . . C62 C 0.3958(4) 0.4683(5) 0.6851(3) 0.0543(18) Uani 1 1 d . . . H62A H 0.3979 0.5092 0.7178 0.081 Uiso 1 1 calc . . GR H62B H 0.4362 0.4872 0.6717 0.081 Uiso 1 1 calc . . GR H62C H 0.4007 0.3979 0.6960 0.081 Uiso 1 1 calc . . GR 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 Br2 0.0425(3) 0.0633(4) 0.0431(4) 0.0025(3) 0.0277(3) -0.0090(3) Br5 0.0603(4) 0.0484(4) 0.0575(5) 0.0075(3) 0.0413(4) -0.0010(3) Br1 0.0381(3) 0.0207(3) 0.0967(6) -0.0068(3) 0.0137(3) -0.0061(3) Br3 0.0518(4) 0.0585(4) 0.0356(4) -0.0108(3) 0.0134(3) -0.0130(3) Br6 0.0559(4) 0.0788(5) 0.0365(4) -0.0210(4) 0.0131(3) -0.0227(4) Br4 0.0410(4) 0.0263(4) 0.1388(8) -0.0179(4) 0.0075(4) -0.0077(3) O5 0.0261(18) 0.044(2) 0.030(2) 0.0108(18) 0.0118(17) 0.0036(17) O2 0.0220(17) 0.042(2) 0.034(2) 0.0086(18) 0.0143(16) -0.0030(16) O1 0.045(2) 0.018(2) 0.039(3) 0.0027(17) 0.0113(19) -0.0054(16) O3 0.044(2) 0.033(2) 0.032(2) -0.0072(18) 0.0174(18) 0.0066(17) C4 0.020(2) 0.020(3) 0.026(3) 0.002(2) 0.004(2) -0.002(2) O4 0.038(2) 0.025(2) 0.042(3) -0.0001(18) 0.0100(18) -0.0079(17) C37 0.023(2) 0.019(3) 0.038(3) 0.001(2) 0.009(2) 0.002(2) O6 0.037(2) 0.037(2) 0.047(3) -0.010(2) 0.015(2) 0.0042(18) C41 0.032(3) 0.021(3) 0.030(3) -0.007(2) 0.014(2) -0.003(2) C5 0.026(3) 0.025(3) 0.035(3) -0.003(2) 0.015(2) 0.003(2) C1 0.027(3) 0.027(3) 0.029(3) 0.003(2) 0.007(2) -0.002(2) C3 0.020(2) 0.024(3) 0.028(3) -0.002(2) 0.008(2) -0.002(2) C48 0.031(3) 0.022(3) 0.033(3) 0.001(2) 0.019(2) -0.002(2) C55 0.036(3) 0.024(3) 0.034(3) -0.003(2) 0.017(3) -0.002(2) C42 0.040(3) 0.021(3) 0.039(4) 0.000(3) 0.008(3) -0.003(2) C8 0.024(3) 0.019(3) 0.035(3) -0.002(2) 0.012(2) 0.000(2) C50 0.054(4) 0.026(3) 0.023(3) 0.003(2) 0.015(3) 0.002(3) C13 0.031(3) 0.028(3) 0.034(3) 0.004(3) 0.008(3) 0.003(2) C43 0.030(3) 0.019(3) 0.064(5) 0.004(3) 0.005(3) 0.001(2) C60 0.027(3) 0.045(4) 0.045(4) -0.017(3) 0.013(3) -0.009(3) C15 0.026(3) 0.026(3) 0.023(3) -0.001(2) 0.011(2) -0.004(2) C38 0.036(3) 0.018(3) 0.036(3) -0.004(2) 0.013(3) -0.003(2) C53 0.031(3) 0.041(3) 0.031(3) 0.005(3) 0.012(3) 0.003(2) C51 0.044(3) 0.026(3) 0.031(3) -0.006(2) 0.021(3) -0.005(2) C46 0.032(3) 0.037(3) 0.033(4) 0.000(3) 0.010(3) 0.003(3) C35 0.027(3) 0.024(3) 0.038(3) -0.008(2) 0.016(2) 0.002(2) C49 0.034(3) 0.031(3) 0.023(3) -0.001(2) 0.008(2) -0.003(2) C21 0.034(3) 0.031(3) 0.035(4) -0.003(3) 0.017(3) 0.002(2) C63 0.029(3) 0.024(3) 0.034(3) -0.005(2) 0.007(2) -0.002(2) C56 0.029(3) 0.036(3) 0.041(4) 0.008(3) 0.011(3) 0.005(2) C12 0.031(3) 0.030(3) 0.037(4) -0.003(3) 0.009(3) -0.006(2) C10 0.031(3) 0.029(3) 0.051(4) 0.007(3) 0.009(3) -0.003(2) C22 0.039(3) 0.026(3) 0.032(3) -0.001(2) 0.019(3) 0.001(2) C58 0.035(3) 0.038(3) 0.026(3) -0.001(3) 0.010(2) -0.009(3) C16 0.030(3) 0.038(3) 0.029(3) 0.005(3) 0.013(2) 0.000(2) C36 0.018(2) 0.019(3) 0.032(3) -0.003(2) 0.007(2) -0.003(2) C18 0.036(3) 0.030(3) 0.037(4) -0.011(3) 0.026(3) -0.012(2) C44 0.027(3) 0.025(3) 0.072(5) -0.015(3) 0.016(3) -0.006(2) C20 0.025(3) 0.026(3) 0.029(3) -0.003(2) 0.009(2) -0.002(2) C17 0.028(3) 0.038(3) 0.039(4) 0.002(3) 0.016(3) 0.001(2) C9 0.027(3) 0.027(3) 0.040(4) 0.002(3) 0.005(2) -0.002(2) C23 0.035(3) 0.037(3) 0.031(3) 0.005(3) 0.008(3) 0.010(3) C57 0.027(3) 0.044(4) 0.041(4) 0.009(3) 0.007(3) -0.007(3) C25 0.041(3) 0.032(3) 0.026(3) 0.000(2) 0.015(3) -0.009(3) C59 0.030(3) 0.041(4) 0.050(4) -0.014(3) 0.018(3) -0.004(3) C47 0.022(3) 0.033(3) 0.032(3) -0.003(2) 0.006(2) 0.004(2) C14 0.021(2) 0.035(3) 0.030(3) 0.002(2) 0.008(2) -0.001(2) C54 0.040(3) 0.027(3) 0.038(4) -0.010(3) 0.017(3) -0.008(2) C61 0.046(3) 0.029(3) 0.046(4) -0.011(3) 0.021(3) -0.001(3) C45 0.027(3) 0.043(4) 0.043(4) -0.015(3) 0.003(3) 0.000(3) C40 0.032(3) 0.029(3) 0.041(4) -0.004(3) 0.006(3) -0.005(2) C34 0.035(3) 0.022(3) 0.034(3) -0.005(2) 0.014(3) 0.001(2) C7 0.036(3) 0.032(3) 0.032(3) 0.007(3) 0.012(3) -0.001(2) C30 0.042(3) 0.030(3) 0.036(4) -0.010(3) 0.018(3) 0.001(3) C2 0.027(3) 0.021(3) 0.028(3) -0.001(2) 0.011(2) 0.000(2) C33 0.056(4) 0.023(3) 0.051(4) 0.001(3) 0.017(3) -0.003(3) C27 0.032(3) 0.045(4) 0.048(4) -0.011(3) 0.019(3) -0.001(3) C26 0.033(3) 0.045(4) 0.048(4) -0.015(3) 0.018(3) 0.000(3) C28 0.028(3) 0.036(3) 0.043(4) -0.004(3) 0.017(3) -0.003(2) C6 0.029(3) 0.021(3) 0.031(3) 0.000(2) 0.014(2) 0.001(2) C32 0.030(3) 0.025(3) 0.032(3) -0.002(2) 0.009(2) -0.012(2) C11 0.024(3) 0.023(3) 0.054(4) -0.008(3) 0.018(3) -0.006(2) C64 0.062(4) 0.025(3) 0.050(4) -0.004(3) 0.006(3) -0.001(3) C52 0.031(3) 0.030(3) 0.048(4) -0.001(3) 0.016(3) 0.000(2) C66 0.063(4) 0.057(5) 0.071(5) -0.011(4) 0.034(4) -0.014(4) C19 0.042(3) 0.026(3) 0.026(3) -0.003(2) 0.014(3) -0.011(2) C24 0.033(3) 0.041(4) 0.044(4) 0.010(3) 0.009(3) 0.005(3) C29 0.060(4) 0.042(4) 0.036(4) 0.010(3) 0.021(3) 0.003(3) C31 0.043(3) 0.040(4) 0.042(4) -0.014(3) 0.007(3) -0.005(3) C65 0.044(3) 0.038(4) 0.038(4) -0.001(3) 0.005(3) -0.002(3) C39 0.032(3) 0.026(3) 0.035(3) -0.004(3) 0.013(2) -0.003(2) C62 0.071(4) 0.038(4) 0.047(4) -0.015(3) 0.011(4) -0.005(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 Br2 C18 1.899(5) . ? Br5 C51 1.904(5) . ? Br1 C11 1.906(5) . ? Br3 C25 1.913(5) . ? Br6 C58 1.897(6) . ? Br4 C44 1.904(5) . ? O5 C48 1.371(6) . ? O5 C47 1.439(6) . ? O2 C15 1.372(6) . ? O2 C14 1.440(6) . ? O1 C8 1.375(6) . ? O1 C7 1.415(6) . ? O3 C21 1.453(6) . ? O3 C22 1.380(6) . ? C4 C5 1.394(7) . ? C4 C3 1.411(7) . ? C4 C32 1.514(7) . ? O4 C41 1.367(6) . ? O4 C40 1.446(6) . ? C37 C38 1.405(7) . ? C37 C63 1.522(7) . ? C37 C36 1.410(7) . ? O6 C55 1.368(6) . ? O6 C54 1.424(6) . ? C41 C42 1.368(7) . ? C41 C46 1.395(7) . ? C5 C21 1.510(7) . ? C5 C6 1.394(7) . ? C1 C7 1.523(7) . ? C1 C2 1.392(7) . ? C1 C6 1.414(7) . ? C3 C14 1.496(7) . ? C3 C2 1.402(7) . ? C48 C53 1.400(7) . ? C48 C49 1.384(7) . ? C55 C60 1.371(7) . ? C55 C56 1.392(7) . ? C42 H42 0.9500 . ? C42 C43 1.377(7) . ? C8 C13 1.373(7) . ? C8 C9 1.384(7) . ? C50 H50 0.9500 . ? C50 C51 1.364(7) . ? C50 C49 1.392(7) . ? C13 H13 0.9500 . ? C13 C12 1.391(7) . ? C43 H43 0.9500 . ? C43 C44 1.380(8) . ? C60 H60 0.9500 . ? C60 C59 1.377(8) . ? C15 C16 1.393(7) . ? C15 C20 1.374(7) . ? C38 C54 1.508(7) . ? C38 C39 1.409(7) . ? C53 H53 0.9500 . ? C53 C52 1.380(7) . ? C51 C52 1.381(8) . ? C46 H46 0.9500 . ? C46 C45 1.377(8) . ? C35 C36 1.399(7) . ? C35 C61 1.520(7) . ? C35 C34 1.413(7) . ? C49 H49 0.9500 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C63 C64 1.523(7) . ? C56 H56 0.9500 . ? C56 C57 1.389(8) . ? C12 H12 0.9500 . ? C12 C11 1.372(8) . ? C10 H10 0.9500 . ? C10 C9 1.387(7) . ? C10 C11 1.384(8) . ? C22 C23 1.379(7) . ? C22 C27 1.393(7) . ? C58 C57 1.369(8) . ? C58 C59 1.377(7) . ? C16 H16 0.9500 . ? C16 C17 1.381(7) . ? C36 C47 1.499(7) . ? C18 C17 1.373(8) . ? C18 C19 1.376(7) . ? C44 C45 1.377(8) . ? C20 H20 0.9500 . ? C20 C19 1.388(7) . ? C17 H17 0.9500 . ? C9 H9 0.9500 . ? C23 H23 0.9500 . ? C23 C24 1.388(8) . ? C57 H57 0.9500 . ? C25 C26 1.373(7) . ? C25 C24 1.380(8) . ? C59 H59 0.9500 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C61 C62 1.536(8) . ? C45 H45 0.9500 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C40 C34 1.515(7) . ? C34 C39 1.418(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 C2 1.508(7) . ? C30 C31 1.528(8) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C33 C32 1.533(7) . ? C27 H27 0.9500 . ? C27 C26 1.373(8) . ? C26 H26 0.9500 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C6 1.529(7) . ? C28 C29 1.514(8) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C52 H52 0.9500 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C66 C65 1.478(8) . ? C19 H19 0.9500 . ? C24 H24 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C65 C39 1.547(8) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? 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 C48 O5 C47 119.1(4) . . ? C15 O2 C14 117.0(4) . . ? C8 O1 C7 117.9(4) . . ? C22 O3 C21 117.7(4) . . ? C5 C4 C3 119.0(4) . . ? C5 C4 C32 121.0(5) . . ? C3 C4 C32 120.0(5) . . ? C41 O4 C40 116.0(4) . . ? C38 C37 C63 119.2(5) . . ? C38 C37 C36 119.5(5) . . ? C36 C37 C63 121.2(5) . . ? C55 O6 C54 116.7(4) . . ? O4 C41 C42 125.5(5) . . ? O4 C41 C46 115.7(5) . . ? C42 C41 C46 118.8(5) . . ? C4 C5 C21 118.3(5) . . ? C6 C5 C4 120.5(5) . . ? C6 C5 C21 121.2(5) . . ? C2 C1 C7 119.4(5) . . ? C2 C1 C6 120.8(5) . . ? C6 C1 C7 119.8(5) . . ? C4 C3 C14 119.2(4) . . ? C2 C3 C4 121.4(5) . . ? C2 C3 C14 119.4(5) . . ? O5 C48 C53 114.5(5) . . ? O5 C48 C49 125.1(4) . . ? C49 C48 C53 120.4(5) . . ? O6 C55 C60 124.9(5) . . ? O6 C55 C56 115.1(5) . . ? C60 C55 C56 120.0(5) . . ? C41 C42 H42 119.3 . . ? C41 C42 C43 121.3(5) . . ? C43 C42 H42 119.3 . . ? O1 C8 C9 114.6(5) . . ? C13 C8 O1 125.1(5) . . ? C13 C8 C9 120.2(5) . . ? C51 C50 H50 120.0 . . ? C51 C50 C49 120.0(5) . . ? C49 C50 H50 120.0 . . ? C8 C13 H13 120.0 . . ? C8 C13 C12 120.0(5) . . ? C12 C13 H13 120.0 . . ? C42 C43 H43 120.4 . . ? C42 C43 C44 119.3(6) . . ? C44 C43 H43 120.4 . . ? C55 C60 H60 119.7 . . ? C55 C60 C59 120.6(5) . . ? C59 C60 H60 119.7 . . ? O2 C15 C16 115.6(5) . . ? O2 C15 C20 124.2(4) . . ? C20 C15 C16 120.2(5) . . ? C37 C38 C54 120.9(5) . . ? C37 C38 C39 120.9(5) . . ? C39 C38 C54 118.1(5) . . ? C48 C53 H53 120.3 . . ? C52 C53 C48 119.3(5) . . ? C52 C53 H53 120.3 . . ? C50 C51 Br5 120.7(4) . . ? C50 C51 C52 121.3(5) . . ? C52 C51 Br5 118.0(4) . . ? C41 C46 H46 119.7 . . ? C45 C46 C41 120.6(5) . . ? C45 C46 H46 119.7 . . ? C36 C35 C61 119.3(5) . . ? C36 C35 C34 120.2(5) . . ? C34 C35 C61 120.5(5) . . ? C48 C49 C50 119.3(5) . . ? C48 C49 H49 120.3 . . ? C50 C49 H49 120.3 . . ? O3 C21 C5 107.7(4) . . ? O3 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C5 C21 H21A 110.2 . . ? C5 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C37 C63 H63A 108.9 . . ? C37 C63 H63B 108.9 . . ? C37 C63 C64 113.3(4) . . ? H63A C63 H63B 107.7 . . ? C64 C63 H63A 108.9 . . ? C64 C63 H63B 108.9 . . ? C55 C56 H56 120.4 . . ? C57 C56 C55 119.3(5) . . ? C57 C56 H56 120.4 . . ? C13 C12 H12 120.2 . . ? C11 C12 C13 119.6(5) . . ? C11 C12 H12 120.2 . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C11 C10 C9 119.3(5) . . ? O3 C22 C27 124.0(5) . . ? C23 C22 O3 116.6(5) . . ? C23 C22 C27 119.5(5) . . ? C57 C58 Br6 119.8(4) . . ? C57 C58 C59 121.0(5) . . ? C59 C58 Br6 119.1(4) . . ? C15 C16 H16 119.9 . . ? C17 C16 C15 120.2(5) . . ? C17 C16 H16 119.9 . . ? C37 C36 C47 118.9(5) . . ? C35 C36 C37 120.1(5) . . ? C35 C36 C47 120.8(5) . . ? C17 C18 Br2 120.6(4) . . ? C17 C18 C19 120.5(5) . . ? C19 C18 Br2 118.9(4) . . ? C43 C44 Br4 119.2(5) . . ? C45 C44 Br4 120.2(4) . . ? C45 C44 C43 120.6(5) . . ? C15 C20 H20 120.4 . . ? C15 C20 C19 119.1(5) . . ? C19 C20 H20 120.4 . . ? C16 C17 H17 120.3 . . ? C18 C17 C16 119.5(5) . . ? C18 C17 H17 120.3 . . ? C8 C9 C10 120.0(5) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C22 C23 H23 119.8 . . ? C22 C23 C24 120.4(5) . . ? C24 C23 H23 119.8 . . ? C56 C57 H57 120.1 . . ? C58 C57 C56 119.7(5) . . ? C58 C57 H57 120.1 . . ? C26 C25 Br3 119.1(4) . . ? C26 C25 C24 121.4(5) . . ? C24 C25 Br3 119.4(4) . . ? C60 C59 C58 119.3(5) . . ? C60 C59 H59 120.4 . . ? C58 C59 H59 120.4 . . ? O5 C47 C36 104.5(4) . . ? O5 C47 H47A 110.8 . . ? O5 C47 H47B 110.8 . . ? C36 C47 H47A 110.8 . . ? C36 C47 H47B 110.8 . . ? H47A C47 H47B 108.9 . . ? O2 C14 C3 108.0(4) . . ? O2 C14 H14A 110.1 . . ? O2 C14 H14B 110.1 . . ? C3 C14 H14A 110.1 . . ? C3 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? O6 C54 C38 109.0(4) . . ? O6 C54 H54A 109.9 . . ? O6 C54 H54B 109.9 . . ? C38 C54 H54A 109.9 . . ? C38 C54 H54B 109.9 . . ? H54A C54 H54B 108.3 . . ? C35 C61 H61A 109.1 . . ? C35 C61 H61B 109.1 . . ? C35 C61 C62 112.5(5) . . ? H61A C61 H61B 107.8 . . ? C62 C61 H61A 109.1 . . ? C62 C61 H61B 109.1 . . ? C46 C45 H45 120.3 . . ? C44 C45 C46 119.4(5) . . ? C44 C45 H45 120.3 . . ? O4 C40 H40A 110.2 . . ? O4 C40 H40B 110.2 . . ? O4 C40 C34 107.4(4) . . ? H40A C40 H40B 108.5 . . ? C34 C40 H40A 110.2 . . ? C34 C40 H40B 110.2 . . ? C35 C34 C40 120.5(5) . . ? C35 C34 C39 120.1(5) . . ? C39 C34 C40 119.4(5) . . ? O1 C7 C1 108.6(4) . . ? O1 C7 H7A 110.0 . . ? O1 C7 H7B 110.0 . . ? C1 C7 H7A 110.0 . . ? C1 C7 H7B 110.0 . . ? H7A C7 H7B 108.3 . . ? H30A C30 H30B 107.8 . . ? C2 C30 H30A 109.1 . . ? C2 C30 H30B 109.1 . . ? C2 C30 C31 112.4(4) . . ? C31 C30 H30A 109.1 . . ? C31 C30 H30B 109.1 . . ? C1 C2 C3 118.4(5) . . ? C1 C2 C30 121.2(5) . . ? C3 C2 C30 120.3(5) . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? C22 C27 H27 119.8 . . ? C26 C27 C22 120.4(5) . . ? C26 C27 H27 119.8 . . ? C25 C26 H26 120.3 . . ? C27 C26 C25 119.4(5) . . ? C27 C26 H26 120.3 . . ? H28A C28 H28B 107.9 . . ? C6 C28 H28A 109.1 . . ? C6 C28 H28B 109.1 . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? C29 C28 C6 112.3(4) . . ? C5 C6 C1 119.6(5) . . ? C5 C6 C28 120.2(5) . . ? C1 C6 C28 120.1(4) . . ? C4 C32 C33 110.7(4) . . ? C4 C32 H32A 109.5 . . ? C4 C32 H32B 109.5 . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? C12 C11 Br1 119.9(4) . . ? C12 C11 C10 120.8(5) . . ? C10 C11 Br1 119.3(4) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C53 C52 C51 119.7(5) . . ? C53 C52 H52 120.1 . . ? C51 C52 H52 120.1 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? C18 C19 C20 120.6(5) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C23 C24 H24 120.6 . . ? C25 C24 C23 118.9(5) . . ? C25 C24 H24 120.6 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C66 C65 H65A 109.5 . . ? C66 C65 H65B 109.5 . . ? C66 C65 C39 110.6(5) . . ? H65A C65 H65B 108.1 . . ? C39 C65 H65A 109.5 . . ? C39 C65 H65B 109.5 . . ? C38 C39 C34 118.7(5) . . ? C38 C39 C65 120.3(5) . . ? C34 C39 C65 121.0(5) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 -177.0(4) . . . . ? Br2 C18 C19 C20 177.2(4) . . . . ? Br5 C51 C52 C53 -179.6(4) . . . . ? Br3 C25 C26 C27 178.2(5) . . . . ? Br3 C25 C24 C23 -177.4(4) . . . . ? Br6 C58 C57 C56 178.8(4) . . . . ? Br6 C58 C59 C60 -179.4(5) . . . . ? Br4 C44 C45 C46 178.7(4) . . . . ? O5 C48 C53 C52 179.1(5) . . . . ? O5 C48 C49 C50 -179.5(5) . . . . ? O2 C15 C16 C17 -179.4(5) . . . . ? O2 C15 C20 C19 179.6(5) . . . . ? O1 C8 C13 C12 -176.8(5) . . . . ? O1 C8 C9 C10 177.2(5) . . . . ? O3 C22 C23 C24 -179.8(5) . . . . ? O3 C22 C27 C26 -179.5(5) . . . . ? C4 C5 C21 O3 72.6(6) . . . . ? C4 C5 C6 C1 -2.2(7) . . . . ? C4 C5 C6 C28 179.0(4) . . . . ? C4 C3 C14 O2 -82.4(6) . . . . ? C4 C3 C2 C1 -4.0(7) . . . . ? C4 C3 C2 C30 179.5(5) . . . . ? O4 C41 C42 C43 -179.9(5) . . . . ? O4 C41 C46 C45 -179.8(5) . . . . ? O4 C40 C34 C35 72.1(6) . . . . ? O4 C40 C34 C39 -111.2(5) . . . . ? C37 C38 C54 O6 89.8(6) . . . . ? C37 C38 C39 C34 7.8(7) . . . . ? C37 C38 C39 C65 -173.6(5) . . . . ? C37 C36 C47 O5 -86.3(5) . . . . ? O6 C55 C60 C59 178.5(5) . . . . ? O6 C55 C56 C57 -179.3(5) . . . . ? C41 O4 C40 C34 179.8(4) . . . . ? C41 C42 C43 C44 0.0(9) . . . . ? C41 C46 C45 C44 -0.4(8) . . . . ? C5 C4 C3 C14 178.7(4) . . . . ? C5 C4 C3 C2 -1.2(7) . . . . ? C5 C4 C32 C33 86.5(6) . . . . ? C3 C4 C5 C21 -177.2(4) . . . . ? C3 C4 C5 C6 4.3(7) . . . . ? C3 C4 C32 C33 -90.8(6) . . . . ? C48 O5 C47 C36 174.6(4) . . . . ? C48 C53 C52 C51 1.3(8) . . . . ? C55 O6 C54 C38 -174.9(4) . . . . ? C55 C60 C59 C58 -0.4(9) . . . . ? C55 C56 C57 C58 1.7(8) . . . . ? C42 C41 C46 C45 1.3(8) . . . . ? C42 C43 C44 Br4 -178.5(4) . . . . ? C42 C43 C44 C45 0.9(9) . . . . ? C8 O1 C7 C1 173.9(4) . . . . ? C8 C13 C12 C11 -1.0(8) . . . . ? C50 C51 C52 C53 -0.9(9) . . . . ? C13 C8 C9 C10 -3.0(8) . . . . ? C13 C12 C11 Br1 177.3(4) . . . . ? C13 C12 C11 C10 -1.9(8) . . . . ? C43 C44 C45 C46 -0.7(9) . . . . ? C60 C55 C56 C57 -1.1(8) . . . . ? C15 O2 C14 C3 178.6(4) . . . . ? C15 C16 C17 C18 -0.8(8) . . . . ? C15 C20 C19 C18 0.4(8) . . . . ? C38 C37 C63 C64 89.8(6) . . . . ? C38 C37 C36 C35 -0.4(7) . . . . ? C38 C37 C36 C47 174.1(4) . . . . ? C53 C48 C49 C50 1.0(8) . . . . ? C51 C50 C49 C48 -0.6(8) . . . . ? C46 C41 C42 C43 -1.1(8) . . . . ? C35 C36 C47 O5 88.2(5) . . . . ? C35 C34 C39 C38 -4.2(7) . . . . ? C35 C34 C39 C65 177.2(5) . . . . ? C49 C48 C53 C52 -1.4(8) . . . . ? C49 C50 C51 Br5 179.3(4) . . . . ? C49 C50 C51 C52 0.5(8) . . . . ? C21 O3 C22 C23 168.9(5) . . . . ? C21 O3 C22 C27 -9.9(8) . . . . ? C21 C5 C6 C1 179.4(5) . . . . ? C21 C5 C6 C28 0.7(7) . . . . ? C63 C37 C38 C54 -3.7(7) . . . . ? C63 C37 C38 C39 172.4(4) . . . . ? C63 C37 C36 C35 -178.3(4) . . . . ? C63 C37 C36 C47 -3.7(7) . . . . ? C56 C55 C60 C59 0.5(9) . . . . ? C22 O3 C21 C5 -170.1(4) . . . . ? C22 C23 C24 C25 -0.2(9) . . . . ? C22 C27 C26 C25 -1.4(9) . . . . ? C16 C15 C20 C19 0.0(8) . . . . ? C36 C37 C38 C54 178.4(5) . . . . ? C36 C37 C38 C39 -5.5(7) . . . . ? C36 C37 C63 C64 -92.4(6) . . . . ? C36 C35 C61 C62 79.1(6) . . . . ? C36 C35 C34 C40 175.0(4) . . . . ? C36 C35 C34 C39 -1.6(7) . . . . ? C20 C15 C16 C17 0.1(8) . . . . ? C17 C18 C19 C20 -1.0(8) . . . . ? C9 C8 C13 C12 3.4(8) . . . . ? C9 C10 C11 Br1 -176.8(4) . . . . ? C9 C10 C11 C12 2.4(9) . . . . ? C23 C22 C27 C26 1.8(9) . . . . ? C57 C58 C59 C60 1.1(9) . . . . ? C59 C58 C57 C56 -1.7(9) . . . . ? C47 O5 C48 C53 -176.2(5) . . . . ? C47 O5 C48 C49 4.3(7) . . . . ? C14 O2 C15 C16 -175.6(5) . . . . ? C14 O2 C15 C20 4.9(7) . . . . ? C14 C3 C2 C1 176.1(4) . . . . ? C14 C3 C2 C30 -0.4(7) . . . . ? C54 O6 C55 C60 -10.6(8) . . . . ? C54 O6 C55 C56 167.5(5) . . . . ? C54 C38 C39 C34 -176.0(5) . . . . ? C54 C38 C39 C65 2.6(7) . . . . ? C61 C35 C36 C37 -174.5(4) . . . . ? C61 C35 C36 C47 11.0(7) . . . . ? C61 C35 C34 C40 -6.5(7) . . . . ? C61 C35 C34 C39 176.9(5) . . . . ? C40 O4 C41 C42 -22.3(7) . . . . ? C40 O4 C41 C46 158.8(5) . . . . ? C40 C34 C39 C38 179.1(4) . . . . ? C40 C34 C39 C65 0.5(7) . . . . ? C34 C35 C36 C37 3.9(7) . . . . ? C34 C35 C36 C47 -170.5(4) . . . . ? C34 C35 C61 C62 -99.4(6) . . . . ? C7 O1 C8 C13 -0.7(7) . . . . ? C7 O1 C8 C9 179.1(5) . . . . ? C7 C1 C2 C3 -172.0(5) . . . . ? C7 C1 C2 C30 4.4(7) . . . . ? C7 C1 C6 C5 175.0(4) . . . . ? C7 C1 C6 C28 -6.3(7) . . . . ? C2 C1 C7 O1 -112.8(5) . . . . ? C2 C1 C6 C5 -3.1(8) . . . . ? C2 C1 C6 C28 175.6(5) . . . . ? C2 C3 C14 O2 97.5(5) . . . . ? C27 C22 C23 C24 -0.9(9) . . . . ? C26 C25 C24 C23 0.5(9) . . . . ? C6 C5 C21 O3 -109.0(5) . . . . ? C6 C1 C7 O1 69.0(6) . . . . ? C6 C1 C2 C3 6.2(7) . . . . ? C6 C1 C2 C30 -177.4(5) . . . . ? C32 C4 C5 C21 5.4(7) . . . . ? C32 C4 C5 C6 -173.1(5) . . . . ? C32 C4 C3 C14 -3.9(7) . . . . ? C32 C4 C3 C2 176.3(4) . . . . ? C11 C10 C9 C8 0.1(9) . . . . ? C66 C65 C39 C38 -99.6(6) . . . . ? C66 C65 C39 C34 79.0(7) . . . . ? C19 C18 C17 C16 1.2(8) . . . . ? C24 C25 C26 C27 0.3(9) . . . . ? C29 C28 C6 C5 77.4(6) . . . . ? C29 C28 C6 C1 -101.4(6) . . . . ? C31 C30 C2 C1 -89.5(6) . . . . ? C31 C30 C2 C3 86.9(6) . . . . ? C39 C38 C54 O6 -86.3(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962413' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-gf-226K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-gf, 226 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Br3 O3' _chemical_formula_sum 'C33 H33 Br3 O3' _chemical_formula_weight 717.32 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 19.2670(8) _cell_length_b 13.4479(5) _cell_length_c 25.3027(16) _cell_angle_alpha 90.00 _cell_angle_beta 109.815(6) _cell_angle_gamma 90.00 _cell_volume 6167.8(5) _cell_formula_units_Z 8 _cell_measurement_reflns_used 3569 _cell_measurement_temperature 226(2) _cell_measurement_theta_max 29.1095 _cell_measurement_theta_min 3.4730 _exptl_absorpt_coefficient_mu 3.956 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.58239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2880 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0806 _diffrn_reflns_av_unetI/netI 0.1285 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 38333 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.17 _diffrn_reflns_theta_min 3.48 _diffrn_ambient_temperature 226(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0293993000 _diffrn_orient_matrix_UB_12 -0.0332034000 _diffrn_orient_matrix_UB_13 -0.0131747000 _diffrn_orient_matrix_UB_21 0.0016047000 _diffrn_orient_matrix_UB_22 0.0135309000 _diffrn_orient_matrix_UB_23 -0.0266519000 _diffrn_orient_matrix_UB_31 0.0257810000 _diffrn_orient_matrix_UB_32 -0.0386850000 _diffrn_orient_matrix_UB_33 0.0019783000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 6682 _reflns_number_total 14411 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 2.503 _refine_diff_density_min -1.099 _refine_diff_density_rms 0.124 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 14411 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1953 _refine_ls_R_factor_gt 0.0824 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1046P)^2^+0.0434P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1825 _refine_ls_wR_factor_ref 0.2408 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C63(H63A,H63B), C47(H47A,H47B), C14(H14A,H14B), C54(H54A, H54B), C61(H61A,H61B), C40(H40A,H40B), C7(H7A,H7B), C30(H30A,H30B), C28(H28A, H28B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C42(H42), C50(H50), C13(H13), C43(H43), C60(H60), C53(H53), C46(H46), C49(H49), C56(H56), C12(H12), C10(H10), C16(H16), C20(H20), C17(H17), C9(H9), C23(H23), C57(H57), C59(H59), C45(H45), C27(H27), C26(H26), C52(H52), C19(H19), C24(H24) 2.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C29(H29A,H29B, H29C), C31(H31A,H31B,H31C), C62(H62A,H62B,H62C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br2 Br 0.45687(4) 0.17930(7) 0.71679(4) 0.0587(3) Uani 1 1 d . . . Br5 Br -0.01659(5) 0.15728(7) 0.73316(4) 0.0646(3) Uani 1 1 d . . . Br1 Br 1.02448(4) 1.00710(6) 0.59293(5) 0.0671(3) Uani 1 1 d . . . Br3 Br 0.66213(5) -0.03176(7) 0.22232(4) 0.0630(3) Uani 1 1 d . . . Br6 Br 0.16241(5) -0.05414(8) 0.21301(4) 0.0714(3) Uani 1 1 d . . . Br4 Br 0.53405(5) 1.00403(6) 0.60033(6) 0.0899(4) Uani 1 1 d . . . O5 O 0.1877(2) 0.2979(4) 0.6136(2) 0.0397(12) Uani 1 1 d . . . O2 O 0.6825(2) 0.2969(4) 0.6119(2) 0.0397(12) Uani 1 1 d . . . O1 O 0.9037(3) 0.5897(3) 0.5592(2) 0.0462(13) Uani 1 1 d . . . O3 O 0.7609(3) 0.2300(4) 0.4286(2) 0.0468(13) Uani 1 1 d . . . C4 C 0.7997(3) 0.2467(5) 0.5549(3) 0.0300(15) Uani 1 1 d . . . O4 O 0.4153(2) 0.5854(3) 0.5747(2) 0.0454(13) Uani 1 1 d . . . C37 C 0.2900(3) 0.2534(5) 0.5439(3) 0.0343(16) Uani 1 1 d . . . O6 O 0.2356(3) 0.2241(4) 0.4095(2) 0.0505(14) Uani 1 1 d . . . C41 C 0.4403(3) 0.6817(5) 0.5771(3) 0.0350(16) Uani 1 1 d . . . C5 C 0.8377(4) 0.2808(5) 0.5204(3) 0.0387(17) Uani 1 1 d . . . C1 C 0.8811(4) 0.4240(5) 0.5813(3) 0.0397(17) Uani 1 1 d . . . C3 C 0.7999(3) 0.3058(5) 0.6011(3) 0.0305(15) Uani 1 1 d . . . C48 C 0.1455(3) 0.2649(5) 0.6441(3) 0.0336(16) Uani 1 1 d . . . C55 C 0.2227(4) 0.1612(5) 0.3646(3) 0.0368(17) Uani 1 1 d . . . C42 C 0.4130(4) 0.7507(5) 0.5354(3) 0.0414(18) Uani 1 1 d . . . H42 H 0.3748 0.7336 0.5021 0.050 Uiso 1 1 calc . . R C8 C 0.9368(3) 0.6818(5) 0.5694(3) 0.0323(16) Uani 1 1 d . . . C50 C 0.1248(4) 0.1866(5) 0.7229(3) 0.0429(18) Uani 1 1 d . . . H50 H 0.1429 0.1549 0.7581 0.051 Uiso 1 1 calc . . R C13 C 0.9947(4) 0.7066(5) 0.6168(3) 0.0406(18) Uani 1 1 d . . . H13 H 1.0160 0.6584 0.6444 0.049 Uiso 1 1 calc . . R C43 C 0.4423(4) 0.8461(5) 0.5426(4) 0.050(2) Uani 1 1 d . . . H43 H 0.4238 0.8934 0.5139 0.060 Uiso 1 1 calc . . R C60 C 0.2780(4) 0.1093(6) 0.3533(4) 0.052(2) Uani 1 1 d . . . H60 H 0.3276 0.1167 0.3764 0.063 Uiso 1 1 calc . . R C15 C 0.6343(3) 0.2689(5) 0.6387(3) 0.0304(15) Uani 1 1 d . . . C38 C 0.3086(4) 0.2915(5) 0.4990(3) 0.0413(18) Uani 1 1 d . . . C53 C 0.0698(4) 0.2796(6) 0.6193(3) 0.0433(18) Uani 1 1 d . . . H53 H 0.0509 0.3117 0.5843 0.052 Uiso 1 1 calc . . R C51 C 0.0506(4) 0.2013(5) 0.6980(3) 0.0393(17) Uani 1 1 d . . . C46 C 0.4967(4) 0.7083(6) 0.6263(3) 0.0437(18) Uani 1 1 d . . . H46 H 0.5156 0.6612 0.6551 0.052 Uiso 1 1 calc . . R C35 C 0.3134(3) 0.4176(5) 0.5877(3) 0.0381(17) Uani 1 1 d . . . C49 C 0.1738(4) 0.2183(5) 0.6966(3) 0.0384(17) Uani 1 1 d . . . H49 H 0.2248 0.2086 0.7138 0.046 Uiso 1 1 calc . . R C21 C 0.8345(4) 0.2186(5) 0.4701(3) 0.0394(17) Uani 1 1 d . . . H21A H 0.8719 0.2410 0.4545 0.047 Uiso 1 1 calc . . R H21B H 0.8440 0.1486 0.4810 0.047 Uiso 1 1 calc . . R C63 C 0.2652(3) 0.1467(5) 0.5438(3) 0.0359(17) Uani 1 1 d . . . H63A H 0.2385 0.1262 0.5051 0.043 Uiso 1 1 calc . . R H63B H 0.2310 0.1423 0.5649 0.043 Uiso 1 1 calc . . R C56 C 0.1504(4) 0.1483(6) 0.3322(3) 0.0451(19) Uani 1 1 d . . . H56 H 0.1132 0.1823 0.3411 0.054 Uiso 1 1 calc . . R C12 C 1.0221(4) 0.8045(6) 0.6237(3) 0.0448(19) Uani 1 1 d . . . H12 H 1.0612 0.8227 0.6561 0.054 Uiso 1 1 calc . . R C10 C 0.9350(4) 0.8468(5) 0.5339(3) 0.0429(19) Uani 1 1 d . . . H10 H 0.9152 0.8943 0.5055 0.052 Uiso 1 1 calc . . R C22 C 0.7414(4) 0.1685(5) 0.3825(3) 0.0402(18) Uani 1 1 d . . . C58 C 0.1870(4) 0.0346(5) 0.2751(3) 0.0400(17) Uani 1 1 d . . . C16 C 0.5601(3) 0.2901(5) 0.6101(3) 0.0382(17) Uani 1 1 d . . . H16 H 0.5460 0.3218 0.5749 0.046 Uiso 1 1 calc . . R C36 C 0.2925(3) 0.3177(5) 0.5889(3) 0.0321(16) Uani 1 1 d . . . C18 C 0.5282(4) 0.2199(5) 0.6841(3) 0.0398(18) Uani 1 1 d . . . C44 C 0.4970(4) 0.8719(5) 0.5903(4) 0.050(2) Uani 1 1 d . . . C20 C 0.6546(4) 0.2233(5) 0.6903(3) 0.0382(17) Uani 1 1 d . . . H20 H 0.7045 0.2090 0.7099 0.046 Uiso 1 1 calc . . R C17 C 0.5077(4) 0.2648(5) 0.6334(3) 0.0405(18) Uani 1 1 d . . . H17 H 0.4577 0.2787 0.6140 0.049 Uiso 1 1 calc . . R C9 C 0.9079(3) 0.7501(5) 0.5270(3) 0.0402(18) Uani 1 1 d . . . H9 H 0.8702 0.7314 0.4937 0.048 Uiso 1 1 calc . . R C23 C 0.6689(4) 0.1674(6) 0.3495(3) 0.048(2) Uani 1 1 d . . . H23 H 0.6351 0.2079 0.3590 0.057 Uiso 1 1 calc . . R C57 C 0.1317(4) 0.0849(6) 0.2860(3) 0.049(2) Uani 1 1 d . . . H57 H 0.0823 0.0769 0.2628 0.059 Uiso 1 1 calc . . R C25 C 0.6942(4) 0.0482(5) 0.2889(3) 0.0453(19) Uani 1 1 d . . . C59 C 0.2592(4) 0.0465(6) 0.3076(3) 0.050(2) Uani 1 1 d . . . H59 H 0.2962 0.0118 0.2988 0.060 Uiso 1 1 calc . . R C47 C 0.2661(3) 0.2812(5) 0.6342(3) 0.0376(17) Uani 1 1 d . . . H47A H 0.2771 0.2103 0.6413 0.045 Uiso 1 1 calc . . R H47B H 0.2895 0.3181 0.6691 0.045 Uiso 1 1 calc . . R C14 C 0.7593(3) 0.2700(5) 0.6385(3) 0.0367(17) Uani 1 1 d . . . H14A H 0.7642 0.1977 0.6432 0.044 Uiso 1 1 calc . . R H14B H 0.7793 0.3012 0.6756 0.044 Uiso 1 1 calc . . R C54 C 0.3068(4) 0.2235(5) 0.4504(3) 0.0437(19) Uani 1 1 d . . . H54A H 0.3429 0.2464 0.4336 0.052 Uiso 1 1 calc . . R H54B H 0.3200 0.1556 0.4642 0.052 Uiso 1 1 calc . . R C61 C 0.3215(4) 0.4836(6) 0.6381(3) 0.050(2) Uani 1 1 d . . . H61A H 0.2807 0.4702 0.6520 0.060 Uiso 1 1 calc . . R H61B H 0.3182 0.5534 0.6264 0.060 Uiso 1 1 calc . . R C45 C 0.5248(4) 0.8028(6) 0.6327(4) 0.049(2) Uani 1 1 d . . . H45 H 0.5629 0.8207 0.6658 0.058 Uiso 1 1 calc . . R C40 C 0.3429(4) 0.5662(5) 0.5360(4) 0.049(2) Uani 1 1 d . . . H40A H 0.3404 0.5826 0.4977 0.059 Uiso 1 1 calc . . R H40B H 0.3064 0.6066 0.5455 0.059 Uiso 1 1 calc . . R C34 C 0.3273(4) 0.4558(5) 0.5404(3) 0.0462(19) Uani 1 1 d . . . C7 C 0.9307(4) 0.5154(5) 0.5994(3) 0.0457(19) Uani 1 1 d . . . H7A H 0.9307 0.5389 0.6361 0.055 Uiso 1 1 calc . . R H7B H 0.9814 0.4984 0.6027 0.055 Uiso 1 1 calc . . R C30 C 0.8369(4) 0.4582(6) 0.6625(3) 0.051(2) Uani 1 1 d . . . H30A H 0.7886 0.4516 0.6670 0.061 Uiso 1 1 calc . . R H30B H 0.8437 0.5282 0.6547 0.061 Uiso 1 1 calc . . R C2 C 0.8382(3) 0.3959(5) 0.6135(3) 0.0362(17) Uani 1 1 d . . . C33 C 0.8169(4) 0.0643(5) 0.5755(4) 0.057(2) Uani 1 1 d . . . H33A H 0.8582 0.0641 0.5617 0.086 Uiso 1 1 calc . . GR H33B H 0.7924 0.0002 0.5681 0.086 Uiso 1 1 calc . . GR H33C H 0.8349 0.0768 0.6156 0.086 Uiso 1 1 calc . . GR C27 C 0.7903(4) 0.1072(6) 0.3681(4) 0.051(2) Uani 1 1 d . . . H27 H 0.8403 0.1064 0.3909 0.061 Uiso 1 1 calc . . R C26 C 0.7670(4) 0.0477(6) 0.3211(3) 0.048(2) Uani 1 1 d . . . H26 H 0.8007 0.0074 0.3114 0.058 Uiso 1 1 calc . . R C28 C 0.9221(4) 0.4038(6) 0.4962(3) 0.048(2) Uani 1 1 d . . . H28A H 0.9598 0.4518 0.5170 0.057 Uiso 1 1 calc . . R H28B H 0.9473 0.3472 0.4862 0.057 Uiso 1 1 calc . . R C6 C 0.8793(3) 0.3676(5) 0.5338(3) 0.0356(16) Uani 1 1 d . . . C32 C 0.7625(3) 0.1458(5) 0.5457(3) 0.0378(17) Uani 1 1 d . . . H32A H 0.7427 0.1315 0.5054 0.045 Uiso 1 1 calc . . R H32B H 0.7212 0.1466 0.5600 0.045 Uiso 1 1 calc . . R C11 C 0.9907(4) 0.8727(5) 0.5823(3) 0.0420(19) Uani 1 1 d . . . C64 C 0.3292(4) 0.0757(5) 0.5696(4) 0.060(2) Uani 1 1 d . . . H64A H 0.3552 0.0948 0.6083 0.090 Uiso 1 1 calc . . GR H64B H 0.3628 0.0787 0.5484 0.090 Uiso 1 1 calc . . GR H64C H 0.3106 0.0085 0.5685 0.090 Uiso 1 1 calc . . GR C52 C 0.0225(4) 0.2466(6) 0.6464(4) 0.047(2) Uani 1 1 d . . . H52 H -0.0287 0.2553 0.6295 0.056 Uiso 1 1 calc . . R C66 C 0.4108(5) 0.4456(8) 0.4500(5) 0.089(3) Uani 1 1 d . . . H66A H 0.4355 0.3828 0.4629 0.133 Uiso 1 1 calc . . GR H66B H 0.4310 0.4962 0.4784 0.133 Uiso 1 1 calc . . GR H66C H 0.4183 0.4652 0.4154 0.133 Uiso 1 1 calc . . GR C19 C 0.6012(4) 0.1987(5) 0.7130(3) 0.0392(17) Uani 1 1 d . . . H19 H 0.6146 0.1673 0.7482 0.047 Uiso 1 1 calc . . R C24 C 0.6441(4) 0.1072(6) 0.3021(4) 0.052(2) Uani 1 1 d . . . H24 H 0.5940 0.1069 0.2796 0.063 Uiso 1 1 calc . . R C29 C 0.8718(5) 0.4519(6) 0.4433(4) 0.062(2) Uani 1 1 d . . . H29A H 0.9007 0.4760 0.4212 0.092 Uiso 1 1 calc . . GR H29B H 0.8461 0.5071 0.4531 0.092 Uiso 1 1 calc . . GR H29C H 0.8361 0.4035 0.4217 0.092 Uiso 1 1 calc . . GR C31 C 0.8975(4) 0.4275(7) 0.7176(4) 0.066(3) Uani 1 1 d . . . H31A H 0.9454 0.4329 0.7132 0.099 Uiso 1 1 calc . . GR H31B H 0.8895 0.3593 0.7266 0.099 Uiso 1 1 calc . . GR H31C H 0.8958 0.4709 0.7478 0.099 Uiso 1 1 calc . . GR C65 C 0.3336(4) 0.4347(6) 0.4401(4) 0.061(2) Uani 1 1 d . . . H65A H 0.3118 0.3892 0.4085 0.073 Uiso 1 1 calc . . R H65B H 0.3090 0.4993 0.4304 0.073 Uiso 1 1 calc . . R C39 C 0.3219(4) 0.3927(6) 0.4943(3) 0.049(2) Uani 1 1 d . . . C62 C 0.3949(5) 0.4669(7) 0.6859(4) 0.070(3) Uani 1 1 d . . . H62A H 0.3961 0.5070 0.7181 0.104 Uiso 1 1 calc . . GR H62B H 0.4354 0.4859 0.6734 0.104 Uiso 1 1 calc . . GR H62C H 0.3996 0.3972 0.6964 0.104 Uiso 1 1 calc . . GR 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 Br2 0.0549(5) 0.0790(6) 0.0555(6) 0.0024(5) 0.0360(4) -0.0118(4) Br5 0.0774(6) 0.0640(6) 0.0746(7) 0.0041(5) 0.0547(5) -0.0053(5) Br1 0.0469(5) 0.0265(4) 0.1199(9) -0.0085(5) 0.0178(5) -0.0082(3) Br3 0.0641(5) 0.0751(6) 0.0477(6) -0.0105(5) 0.0162(4) -0.0158(4) Br6 0.0687(6) 0.0953(8) 0.0473(6) -0.0232(5) 0.0159(5) -0.0256(5) Br4 0.0501(5) 0.0322(5) 0.1674(12) -0.0217(6) 0.0109(6) -0.0098(4) O5 0.032(2) 0.053(3) 0.036(3) 0.011(2) 0.014(2) 0.005(2) O2 0.028(2) 0.054(3) 0.040(3) 0.009(2) 0.015(2) -0.005(2) O1 0.064(3) 0.020(3) 0.052(4) 0.003(2) 0.017(3) -0.005(2) O3 0.059(3) 0.044(3) 0.043(3) -0.004(3) 0.025(3) 0.009(2) C4 0.028(3) 0.028(4) 0.035(4) 0.001(3) 0.013(3) 0.002(3) O4 0.046(3) 0.030(3) 0.060(4) -0.003(2) 0.017(3) -0.008(2) C37 0.035(3) 0.023(4) 0.044(5) -0.005(3) 0.013(3) -0.005(3) O6 0.046(3) 0.051(3) 0.055(4) -0.012(3) 0.019(3) 0.004(2) C41 0.037(4) 0.031(4) 0.038(4) -0.010(3) 0.013(3) -0.002(3) C5 0.046(4) 0.029(4) 0.050(5) -0.008(3) 0.028(4) -0.005(3) C1 0.042(4) 0.036(4) 0.041(5) 0.004(3) 0.014(3) 0.001(3) C3 0.022(3) 0.030(4) 0.042(4) -0.001(3) 0.015(3) 0.000(3) C48 0.036(4) 0.029(4) 0.040(5) -0.003(3) 0.019(3) 0.001(3) C55 0.047(4) 0.027(4) 0.042(5) -0.009(3) 0.023(3) -0.007(3) C42 0.046(4) 0.029(4) 0.043(5) 0.001(3) 0.007(3) -0.002(3) C8 0.029(3) 0.029(4) 0.040(4) -0.002(3) 0.013(3) -0.001(3) C50 0.063(5) 0.033(4) 0.039(5) 0.000(3) 0.024(4) -0.002(4) C13 0.038(4) 0.036(4) 0.047(5) 0.006(4) 0.012(3) 0.000(3) C43 0.050(4) 0.026(4) 0.066(6) 0.009(4) 0.011(4) -0.003(3) C60 0.043(4) 0.056(5) 0.061(6) -0.019(4) 0.021(4) -0.010(4) C15 0.032(3) 0.028(4) 0.034(4) -0.006(3) 0.015(3) -0.006(3) C38 0.052(4) 0.023(4) 0.059(5) -0.007(3) 0.032(4) -0.007(3) C53 0.037(4) 0.055(5) 0.038(5) 0.006(4) 0.013(3) 0.004(3) C51 0.058(5) 0.035(4) 0.033(4) -0.007(3) 0.026(4) -0.007(3) C46 0.050(4) 0.041(5) 0.043(5) -0.003(4) 0.019(4) 0.000(4) C35 0.037(4) 0.035(4) 0.050(5) -0.011(3) 0.024(3) -0.004(3) C49 0.039(4) 0.039(4) 0.039(5) -0.001(3) 0.016(3) -0.001(3) C21 0.048(4) 0.031(4) 0.047(5) 0.000(3) 0.025(4) 0.008(3) C63 0.035(4) 0.025(4) 0.043(5) -0.004(3) 0.008(3) -0.006(3) C56 0.035(4) 0.049(5) 0.053(5) 0.012(4) 0.016(4) 0.008(3) C12 0.039(4) 0.041(5) 0.052(5) -0.006(4) 0.013(4) -0.009(3) C10 0.040(4) 0.029(4) 0.056(5) 0.007(4) 0.011(4) 0.001(3) C22 0.042(4) 0.037(4) 0.046(5) -0.003(4) 0.020(4) 0.001(3) C58 0.041(4) 0.046(4) 0.032(4) 0.000(3) 0.010(3) -0.008(3) C16 0.038(4) 0.044(4) 0.034(4) 0.006(3) 0.015(3) -0.005(3) C36 0.025(3) 0.026(4) 0.046(5) -0.003(3) 0.013(3) -0.001(3) C18 0.041(4) 0.041(4) 0.044(5) -0.006(4) 0.023(4) -0.010(3) C44 0.030(4) 0.024(4) 0.091(7) -0.017(4) 0.015(4) -0.007(3) C20 0.043(4) 0.032(4) 0.042(5) 0.003(3) 0.017(3) -0.001(3) C17 0.036(4) 0.046(5) 0.043(5) 0.000(4) 0.018(3) -0.004(3) C9 0.032(4) 0.030(4) 0.054(5) 0.000(4) 0.008(3) -0.003(3) C23 0.055(5) 0.051(5) 0.042(5) 0.002(4) 0.023(4) 0.013(4) C57 0.032(4) 0.055(5) 0.054(6) 0.009(4) 0.006(4) -0.002(4) C25 0.064(5) 0.039(4) 0.038(5) -0.001(4) 0.023(4) -0.005(4) C59 0.045(4) 0.045(5) 0.064(6) -0.018(4) 0.024(4) -0.007(4) C47 0.035(4) 0.037(4) 0.040(5) -0.007(3) 0.012(3) -0.001(3) C14 0.029(3) 0.045(4) 0.039(4) 0.002(3) 0.015(3) 0.000(3) C54 0.056(5) 0.029(4) 0.057(5) -0.011(4) 0.032(4) -0.009(3) C61 0.056(5) 0.041(5) 0.051(5) -0.021(4) 0.017(4) -0.003(4) C45 0.032(4) 0.052(5) 0.055(6) -0.020(4) 0.007(4) -0.007(4) C40 0.055(5) 0.032(4) 0.060(6) -0.008(4) 0.020(4) -0.009(3) C34 0.055(4) 0.032(4) 0.059(6) -0.009(4) 0.030(4) -0.006(3) C7 0.047(4) 0.049(5) 0.040(5) -0.001(4) 0.013(4) -0.001(4) C30 0.052(5) 0.050(5) 0.058(6) -0.020(4) 0.029(4) -0.005(4) C2 0.037(4) 0.031(4) 0.047(5) -0.010(3) 0.024(3) -0.007(3) C33 0.070(5) 0.033(4) 0.070(6) 0.007(4) 0.024(5) 0.001(4) C27 0.036(4) 0.058(5) 0.063(6) -0.010(4) 0.023(4) 0.004(4) C26 0.039(4) 0.051(5) 0.059(6) -0.021(4) 0.025(4) -0.004(4) C28 0.042(4) 0.055(5) 0.053(5) -0.005(4) 0.025(4) -0.002(4) C6 0.041(4) 0.030(4) 0.042(5) 0.001(3) 0.023(3) -0.001(3) C32 0.039(4) 0.027(4) 0.047(5) -0.008(3) 0.013(3) -0.014(3) C11 0.030(4) 0.029(4) 0.069(6) -0.008(4) 0.020(4) -0.002(3) C64 0.067(5) 0.033(4) 0.063(6) -0.006(4) 0.002(4) 0.000(4) C52 0.037(4) 0.049(5) 0.061(6) 0.000(4) 0.026(4) 0.002(3) C66 0.084(7) 0.086(8) 0.110(10) -0.022(7) 0.049(7) -0.017(6) C19 0.058(5) 0.032(4) 0.033(4) 0.003(3) 0.021(4) -0.006(3) C24 0.040(4) 0.064(6) 0.051(6) 0.024(5) 0.014(4) 0.014(4) C29 0.089(6) 0.055(6) 0.043(5) 0.012(4) 0.024(5) 0.012(5) C31 0.058(5) 0.070(6) 0.063(6) -0.033(5) 0.011(5) -0.008(4) C65 0.061(5) 0.056(6) 0.059(6) 0.001(5) 0.012(4) 0.000(4) C39 0.066(5) 0.038(5) 0.053(5) -0.016(4) 0.032(4) -0.012(4) C62 0.080(6) 0.063(6) 0.059(6) -0.024(5) 0.014(5) -0.015(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br2 C18 1.909(7) . ? Br5 C51 1.897(7) . ? Br1 C11 1.909(7) . ? Br3 C25 1.915(7) . ? Br6 C58 1.901(7) . ? Br4 C44 1.899(7) . ? O5 C48 1.371(8) . ? O5 C47 1.439(7) . ? O2 C15 1.375(7) . ? O2 C14 1.448(7) . ? O1 C8 1.377(8) . ? O1 C7 1.395(8) . ? O3 C21 1.458(8) . ? O3 C22 1.374(9) . ? C4 C5 1.395(9) . ? C4 C3 1.411(9) . ? C4 C32 1.515(9) . ? O4 C41 1.376(8) . ? O4 C40 1.431(8) . ? C37 C38 1.399(10) . ? C37 C63 1.513(9) . ? C37 C36 1.418(9) . ? O6 C55 1.369(8) . ? O6 C54 1.410(8) . ? C41 C42 1.368(10) . ? C41 C46 1.393(10) . ? C5 C21 1.506(10) . ? C5 C6 1.392(9) . ? C1 C7 1.529(10) . ? C1 C2 1.393(9) . ? C1 C6 1.413(10) . ? C3 C14 1.498(9) . ? C3 C2 1.397(9) . ? C48 C53 1.392(9) . ? C48 C49 1.402(10) . ? C55 C60 1.383(10) . ? C55 C56 1.367(9) . ? C42 H42 0.9400 . ? C42 C43 1.388(9) . ? C8 C13 1.374(9) . ? C8 C9 1.379(9) . ? C50 H50 0.9400 . ? C50 C51 1.367(10) . ? C50 C49 1.392(9) . ? C13 H13 0.9400 . ? C13 C12 1.406(10) . ? C43 H43 0.9400 . ? C43 C44 1.350(11) . ? C60 H60 0.9400 . ? C60 C59 1.377(10) . ? C15 C16 1.394(9) . ? C15 C20 1.375(10) . ? C38 C54 1.524(10) . ? C38 C39 1.398(10) . ? C53 H53 0.9400 . ? C53 C52 1.386(10) . ? C51 C52 1.376(10) . ? C46 H46 0.9400 . ? C46 C45 1.369(10) . ? C35 C36 1.406(9) . ? C35 C61 1.519(10) . ? C35 C34 1.408(10) . ? C49 H49 0.9400 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C63 H63A 0.9800 . ? C63 H63B 0.9800 . ? C63 C64 1.521(10) . ? C56 H56 0.9400 . ? C56 C57 1.392(11) . ? C12 H12 0.9400 . ? C12 C11 1.368(10) . ? C10 H10 0.9400 . ? C10 C9 1.391(9) . ? C10 C11 1.373(10) . ? C22 C23 1.364(10) . ? C22 C27 1.391(9) . ? C58 C57 1.365(10) . ? C58 C59 1.365(9) . ? C16 H16 0.9400 . ? C16 C17 1.373(9) . ? C36 C47 1.485(9) . ? C18 C17 1.351(10) . ? C18 C19 1.377(9) . ? C44 C45 1.383(11) . ? C20 H20 0.9400 . ? C20 C19 1.377(9) . ? C17 H17 0.9400 . ? C9 H9 0.9400 . ? C23 H23 0.9400 . ? C23 C24 1.391(11) . ? C57 H57 0.9400 . ? C25 C26 1.363(10) . ? C25 C24 1.376(10) . ? C59 H59 0.9400 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C61 H61A 0.9800 . ? C61 H61B 0.9800 . ? C61 C62 1.533(11) . ? C45 H45 0.9400 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 C34 1.526(10) . ? C34 C39 1.417(10) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 C2 1.504(10) . ? C30 C31 1.541(11) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C33 C32 1.528(10) . ? C27 H27 0.9400 . ? C27 C26 1.377(10) . ? C26 H26 0.9400 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 C6 1.534(9) . ? C28 C29 1.506(10) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C64 H64A 0.9700 . ? C64 H64B 0.9700 . ? C64 H64C 0.9700 . ? C52 H52 0.9400 . ? C66 H66A 0.9700 . ? C66 H66B 0.9700 . ? C66 H66C 0.9700 . ? C66 C65 1.431(11) . ? C19 H19 0.9400 . ? C24 H24 0.9400 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 H31C 0.9700 . ? C65 H65A 0.9800 . ? C65 H65B 0.9800 . ? C65 C39 1.569(11) . ? C62 H62A 0.9700 . ? C62 H62B 0.9700 . ? C62 H62C 0.9700 . ? 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 C48 O5 C47 119.7(5) . . ? C15 O2 C14 117.2(5) . . ? C8 O1 C7 118.2(5) . . ? C22 O3 C21 117.8(5) . . ? C5 C4 C3 118.6(6) . . ? C5 C4 C32 121.3(6) . . ? C3 C4 C32 120.1(6) . . ? C41 O4 C40 116.4(5) . . ? C38 C37 C63 120.9(6) . . ? C38 C37 C36 118.7(6) . . ? C36 C37 C63 120.3(6) . . ? C55 O6 C54 117.6(5) . . ? O4 C41 C46 115.8(6) . . ? C42 C41 O4 124.6(6) . . ? C42 C41 C46 119.6(7) . . ? C4 C5 C21 117.9(6) . . ? C6 C5 C4 120.3(6) . . ? C6 C5 C21 121.7(6) . . ? C2 C1 C7 118.5(7) . . ? C2 C1 C6 120.3(6) . . ? C6 C1 C7 121.2(6) . . ? C4 C3 C14 119.0(6) . . ? C2 C3 C4 121.8(6) . . ? C2 C3 C14 119.1(6) . . ? O5 C48 C53 115.5(6) . . ? O5 C48 C49 124.4(6) . . ? C53 C48 C49 120.1(6) . . ? O6 C55 C60 123.1(6) . . ? C56 C55 O6 116.0(6) . . ? C56 C55 C60 120.8(7) . . ? C41 C42 H42 120.3 . . ? C41 C42 C43 119.5(7) . . ? C43 C42 H42 120.3 . . ? O1 C8 C9 114.4(6) . . ? C13 C8 O1 124.8(6) . . ? C13 C8 C9 120.8(6) . . ? C51 C50 H50 119.8 . . ? C51 C50 C49 120.5(7) . . ? C49 C50 H50 119.8 . . ? C8 C13 H13 120.2 . . ? C8 C13 C12 119.7(7) . . ? C12 C13 H13 120.2 . . ? C42 C43 H43 119.5 . . ? C44 C43 C42 121.0(7) . . ? C44 C43 H43 119.5 . . ? C55 C60 H60 120.6 . . ? C59 C60 C55 118.7(7) . . ? C59 C60 H60 120.6 . . ? O2 C15 C16 115.7(6) . . ? C20 C15 O2 124.6(6) . . ? C20 C15 C16 119.7(6) . . ? C37 C38 C54 119.7(6) . . ? C39 C38 C37 122.1(7) . . ? C39 C38 C54 118.0(7) . . ? C48 C53 H53 120.1 . . ? C52 C53 C48 119.7(7) . . ? C52 C53 H53 120.1 . . ? C50 C51 Br5 120.8(6) . . ? C50 C51 C52 121.0(7) . . ? C52 C51 Br5 118.1(5) . . ? C41 C46 H46 120.0 . . ? C45 C46 C41 120.0(7) . . ? C45 C46 H46 120.0 . . ? C36 C35 C61 119.2(7) . . ? C36 C35 C34 120.4(7) . . ? C34 C35 C61 120.4(6) . . ? C48 C49 H49 120.6 . . ? C50 C49 C48 118.8(6) . . ? C50 C49 H49 120.6 . . ? O3 C21 C5 107.5(5) . . ? O3 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C5 C21 H21A 110.2 . . ? C5 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C37 C63 H63A 109.1 . . ? C37 C63 H63B 109.1 . . ? C37 C63 C64 112.6(5) . . ? H63A C63 H63B 107.8 . . ? C64 C63 H63A 109.1 . . ? C64 C63 H63B 109.1 . . ? C55 C56 H56 119.9 . . ? C55 C56 C57 120.2(7) . . ? C57 C56 H56 119.9 . . ? C13 C12 H12 120.5 . . ? C11 C12 C13 118.9(7) . . ? C11 C12 H12 120.5 . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C11 C10 C9 119.7(7) . . ? O3 C22 C27 124.4(6) . . ? C23 C22 O3 117.1(6) . . ? C23 C22 C27 118.6(7) . . ? C57 C58 Br6 119.0(5) . . ? C59 C58 Br6 119.2(6) . . ? C59 C58 C57 121.8(7) . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.0(7) . . ? C17 C16 H16 120.0 . . ? C37 C36 C47 119.3(6) . . ? C35 C36 C37 119.8(6) . . ? C35 C36 C47 120.6(6) . . ? C17 C18 Br2 121.2(5) . . ? C17 C18 C19 120.9(6) . . ? C19 C18 Br2 117.8(6) . . ? C43 C44 Br4 120.3(6) . . ? C43 C44 C45 119.9(7) . . ? C45 C44 Br4 119.7(6) . . ? C15 C20 H20 120.3 . . ? C15 C20 C19 119.4(6) . . ? C19 C20 H20 120.3 . . ? C16 C17 H17 120.1 . . ? C18 C17 C16 119.8(7) . . ? C18 C17 H17 120.1 . . ? C8 C9 C10 119.3(7) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C22 C23 H23 119.5 . . ? C22 C23 C24 121.0(7) . . ? C24 C23 H23 119.5 . . ? C56 C57 H57 120.8 . . ? C58 C57 C56 118.3(6) . . ? C58 C57 H57 120.8 . . ? C26 C25 Br3 118.9(6) . . ? C26 C25 C24 121.4(7) . . ? C24 C25 Br3 119.6(6) . . ? C60 C59 H59 119.9 . . ? C58 C59 C60 120.2(7) . . ? C58 C59 H59 119.9 . . ? O5 C47 C36 105.1(5) . . ? O5 C47 H47A 110.7 . . ? O5 C47 H47B 110.7 . . ? C36 C47 H47A 110.7 . . ? C36 C47 H47B 110.7 . . ? H47A C47 H47B 108.8 . . ? O2 C14 C3 107.3(5) . . ? O2 C14 H14A 110.3 . . ? O2 C14 H14B 110.3 . . ? C3 C14 H14A 110.3 . . ? C3 C14 H14B 110.3 . . ? H14A C14 H14B 108.5 . . ? O6 C54 C38 109.9(6) . . ? O6 C54 H54A 109.7 . . ? O6 C54 H54B 109.7 . . ? C38 C54 H54A 109.7 . . ? C38 C54 H54B 109.7 . . ? H54A C54 H54B 108.2 . . ? C35 C61 H61A 109.1 . . ? C35 C61 H61B 109.1 . . ? C35 C61 C62 112.4(6) . . ? H61A C61 H61B 107.9 . . ? C62 C61 H61A 109.1 . . ? C62 C61 H61B 109.1 . . ? C46 C45 C44 120.0(7) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? O4 C40 H40A 110.3 . . ? O4 C40 H40B 110.3 . . ? O4 C40 C34 107.2(6) . . ? H40A C40 H40B 108.5 . . ? C34 C40 H40A 110.3 . . ? C34 C40 H40B 110.3 . . ? C35 C34 C40 121.0(7) . . ? C35 C34 C39 119.9(7) . . ? C39 C34 C40 119.0(7) . . ? O1 C7 C1 108.5(6) . . ? O1 C7 H7A 110.0 . . ? O1 C7 H7B 110.0 . . ? C1 C7 H7A 110.0 . . ? C1 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? H30A C30 H30B 107.9 . . ? C2 C30 H30A 109.2 . . ? C2 C30 H30B 109.2 . . ? C2 C30 C31 112.2(6) . . ? C31 C30 H30A 109.2 . . ? C31 C30 H30B 109.2 . . ? C1 C2 C3 118.5(6) . . ? C1 C2 C30 120.6(6) . . ? C3 C2 C30 120.8(6) . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? C22 C27 H27 119.4 . . ? C26 C27 C22 121.3(7) . . ? C26 C27 H27 119.4 . . ? C25 C26 C27 118.9(7) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? H28A C28 H28B 108.0 . . ? C6 C28 H28A 109.3 . . ? C6 C28 H28B 109.3 . . ? C29 C28 H28A 109.3 . . ? C29 C28 H28B 109.3 . . ? C29 C28 C6 111.5(6) . . ? C5 C6 C1 120.2(6) . . ? C5 C6 C28 120.1(6) . . ? C1 C6 C28 119.7(6) . . ? C4 C32 C33 110.9(5) . . ? C4 C32 H32A 109.5 . . ? C4 C32 H32B 109.5 . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? C12 C11 Br1 119.1(6) . . ? C12 C11 C10 121.4(7) . . ? C10 C11 Br1 119.5(6) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C53 C52 H52 120.1 . . ? C51 C52 C53 119.8(7) . . ? C51 C52 H52 120.1 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? C18 C19 H19 119.9 . . ? C20 C19 C18 120.1(7) . . ? C20 C19 H19 119.9 . . ? C23 C24 H24 120.6 . . ? C25 C24 C23 118.8(7) . . ? C25 C24 H24 120.6 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C66 C65 H65A 109.8 . . ? C66 C65 H65B 109.8 . . ? C66 C65 C39 109.4(8) . . ? H65A C65 H65B 108.2 . . ? C39 C65 H65A 109.8 . . ? C39 C65 H65B 109.8 . . ? C38 C39 C34 118.5(7) . . ? C38 C39 C65 120.7(7) . . ? C34 C39 C65 120.7(7) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 C18 C17 C16 -177.8(5) . . . . ? Br2 C18 C19 C20 177.7(5) . . . . ? Br5 C51 C52 C53 -179.8(6) . . . . ? Br3 C25 C26 C27 178.3(6) . . . . ? Br3 C25 C24 C23 -177.7(6) . . . . ? Br6 C58 C57 C56 178.9(6) . . . . ? Br6 C58 C59 C60 -179.0(6) . . . . ? Br4 C44 C45 C46 178.1(6) . . . . ? O5 C48 C53 C52 178.5(6) . . . . ? O5 C48 C49 C50 -178.9(6) . . . . ? O2 C15 C16 C17 179.9(6) . . . . ? O2 C15 C20 C19 180.0(6) . . . . ? O1 C8 C13 C12 -177.4(6) . . . . ? O1 C8 C9 C10 177.3(6) . . . . ? O3 C22 C23 C24 -179.8(7) . . . . ? O3 C22 C27 C26 -179.8(7) . . . . ? C4 C5 C21 O3 73.2(8) . . . . ? C4 C5 C6 C1 -2.4(10) . . . . ? C4 C5 C6 C28 178.9(6) . . . . ? C4 C3 C14 O2 -82.9(7) . . . . ? C4 C3 C2 C1 -4.3(10) . . . . ? C4 C3 C2 C30 179.3(6) . . . . ? O4 C41 C42 C43 179.6(7) . . . . ? O4 C41 C46 C45 -179.5(6) . . . . ? O4 C40 C34 C35 72.5(8) . . . . ? O4 C40 C34 C39 -111.7(8) . . . . ? C37 C38 C54 O6 88.4(8) . . . . ? C37 C38 C39 C34 9.3(11) . . . . ? C37 C38 C39 C65 -172.8(7) . . . . ? C37 C36 C47 O5 -85.3(7) . . . . ? O6 C55 C60 C59 179.0(7) . . . . ? O6 C55 C56 C57 -179.4(7) . . . . ? C41 O4 C40 C34 179.7(6) . . . . ? C41 C42 C43 C44 -0.3(12) . . . . ? C41 C46 C45 C44 0.0(11) . . . . ? C5 C4 C3 C14 180.0(6) . . . . ? C5 C4 C3 C2 -1.4(10) . . . . ? C5 C4 C32 C33 85.8(8) . . . . ? C3 C4 C5 C21 -177.8(6) . . . . ? C3 C4 C5 C6 4.7(10) . . . . ? C3 C4 C32 C33 -90.6(8) . . . . ? C48 O5 C47 C36 175.1(5) . . . . ? C48 C53 C52 C51 1.2(11) . . . . ? C55 O6 C54 C38 -175.3(6) . . . . ? C55 C60 C59 C58 -1.5(12) . . . . ? C55 C56 C57 C58 1.8(11) . . . . ? C42 C41 C46 C45 -0.2(11) . . . . ? C42 C43 C44 Br4 -178.0(6) . . . . ? C42 C43 C44 C45 0.2(12) . . . . ? C8 O1 C7 C1 174.8(6) . . . . ? C8 C13 C12 C11 -1.0(11) . . . . ? C50 C51 C52 C53 -1.0(11) . . . . ? C13 C8 C9 C10 -3.9(11) . . . . ? C13 C12 C11 Br1 177.1(5) . . . . ? C13 C12 C11 C10 -2.0(11) . . . . ? C43 C44 C45 C46 -0.1(12) . . . . ? C60 C55 C56 C57 -2.2(11) . . . . ? C15 O2 C14 C3 178.5(5) . . . . ? C15 C16 C17 C18 0.4(11) . . . . ? C15 C20 C19 C18 -0.1(11) . . . . ? C38 C37 C63 C64 89.0(8) . . . . ? C38 C37 C36 C35 -0.1(9) . . . . ? C38 C37 C36 C47 174.2(6) . . . . ? C53 C48 C49 C50 0.5(10) . . . . ? C51 C50 C49 C48 -0.4(10) . . . . ? C46 C41 C42 C43 0.3(11) . . . . ? C35 C36 C47 O5 88.9(7) . . . . ? C35 C34 C39 C38 -4.9(11) . . . . ? C35 C34 C39 C65 177.2(7) . . . . ? C49 C48 C53 C52 -0.9(11) . . . . ? C49 C50 C51 Br5 179.4(5) . . . . ? C49 C50 C51 C52 0.6(11) . . . . ? C21 O3 C22 C23 168.5(6) . . . . ? C21 O3 C22 C27 -10.5(10) . . . . ? C21 C5 C6 C1 -179.9(6) . . . . ? C21 C5 C6 C28 1.5(10) . . . . ? C63 C37 C38 C54 -2.5(10) . . . . ? C63 C37 C38 C39 171.2(6) . . . . ? C63 C37 C36 C35 -178.0(6) . . . . ? C63 C37 C36 C47 -3.8(9) . . . . ? C56 C55 C60 C59 2.0(12) . . . . ? C22 O3 C21 C5 -170.5(6) . . . . ? C22 C23 C24 C25 0.1(12) . . . . ? C22 C27 C26 C25 -1.1(12) . . . . ? C16 C15 C20 C19 0.3(10) . . . . ? C36 C37 C38 C54 179.6(6) . . . . ? C36 C37 C38 C39 -6.8(10) . . . . ? C36 C37 C63 C64 -93.1(8) . . . . ? C36 C35 C61 C62 79.4(8) . . . . ? C36 C35 C34 C40 174.1(6) . . . . ? C36 C35 C34 C39 -1.7(11) . . . . ? C20 C15 C16 C17 -0.5(10) . . . . ? C17 C18 C19 C20 0.1(11) . . . . ? C9 C8 C13 C12 3.9(11) . . . . ? C9 C10 C11 Br1 -177.1(5) . . . . ? C9 C10 C11 C12 2.0(11) . . . . ? C23 C22 C27 C26 1.2(12) . . . . ? C57 C58 C59 C60 1.1(12) . . . . ? C59 C58 C57 C56 -1.3(12) . . . . ? C47 O5 C48 C53 -176.6(6) . . . . ? C47 O5 C48 C49 2.8(10) . . . . ? C14 O2 C15 C16 -175.9(6) . . . . ? C14 O2 C15 C20 4.5(9) . . . . ? C14 C3 C2 C1 174.4(6) . . . . ? C14 C3 C2 C30 -2.1(10) . . . . ? C54 O6 C55 C60 -10.1(10) . . . . ? C54 O6 C55 C56 167.0(6) . . . . ? C54 C38 C39 C34 -177.0(7) . . . . ? C54 C38 C39 C65 0.9(10) . . . . ? C61 C35 C36 C37 -175.3(6) . . . . ? C61 C35 C36 C47 10.4(9) . . . . ? C61 C35 C34 C40 -6.3(10) . . . . ? C61 C35 C34 C39 177.9(7) . . . . ? C40 O4 C41 C42 -21.0(10) . . . . ? C40 O4 C41 C46 158.3(6) . . . . ? C40 C34 C39 C38 179.2(6) . . . . ? C40 C34 C39 C65 1.3(11) . . . . ? C34 C35 C36 C37 4.2(10) . . . . ? C34 C35 C36 C47 -170.0(6) . . . . ? C34 C35 C61 C62 -100.2(9) . . . . ? C7 O1 C8 C13 -0.1(10) . . . . ? C7 O1 C8 C9 178.6(6) . . . . ? C7 C1 C2 C3 -172.3(6) . . . . ? C7 C1 C2 C30 4.1(10) . . . . ? C7 C1 C6 C5 175.5(6) . . . . ? C7 C1 C6 C28 -5.8(10) . . . . ? C2 C1 C7 O1 -112.7(7) . . . . ? C2 C1 C6 C5 -3.3(10) . . . . ? C2 C1 C6 C28 175.3(6) . . . . ? C2 C3 C14 O2 98.4(7) . . . . ? C27 C22 C23 C24 -0.7(12) . . . . ? C26 C25 C24 C23 0.0(12) . . . . ? C6 C5 C21 O3 -109.3(7) . . . . ? C6 C1 C7 O1 68.4(8) . . . . ? C6 C1 C2 C3 6.6(10) . . . . ? C6 C1 C2 C30 -177.0(7) . . . . ? C32 C4 C5 C21 5.8(9) . . . . ? C32 C4 C5 C6 -171.8(6) . . . . ? C32 C4 C3 C14 -3.5(9) . . . . ? C32 C4 C3 C2 175.2(6) . . . . ? C11 C10 C9 C8 1.0(11) . . . . ? C66 C65 C39 C38 -98.9(9) . . . . ? C66 C65 C39 C34 78.9(10) . . . . ? C19 C18 C17 C16 -0.2(11) . . . . ? C24 C25 C26 C27 0.5(12) . . . . ? C29 C28 C6 C5 76.8(9) . . . . ? C29 C28 C6 C1 -101.9(8) . . . . ? C31 C30 C2 C1 -89.4(9) . . . . ? C31 C30 C2 C3 87.0(8) . . . . ? C39 C38 C54 O6 -85.5(8) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962414' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-gf-262K _audit_creation_date 2013-12-28 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-gf, 262 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Br3 O3' _chemical_formula_sum 'C33 H33 Br3 O3' _chemical_formula_weight 717.32 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6682(4) _cell_length_b 13.4772(7) _cell_length_c 23.8893(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.463(5) _cell_angle_gamma 90.00 _cell_volume 3109.9(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2091 _cell_measurement_temperature 262.0(2) _cell_measurement_theta_max 29.1003 _cell_measurement_theta_min 4.0825 _exptl_absorpt_coefficient_mu 3.923 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.57411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1440 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_unetI/netI 0.0989 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 17096 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.16 _diffrn_reflns_theta_min 4.36 _diffrn_ambient_temperature 262.0(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.840 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0453162000 _diffrn_orient_matrix_UB_12 0.0332287000 _diffrn_orient_matrix_UB_13 -0.0131308000 _diffrn_orient_matrix_UB_21 -0.0298048000 _diffrn_orient_matrix_UB_22 -0.0134607000 _diffrn_orient_matrix_UB_23 -0.0265756000 _diffrn_orient_matrix_UB_31 -0.0494794000 _diffrn_orient_matrix_UB_32 0.0385569000 _diffrn_orient_matrix_UB_33 0.0020596000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3062 _reflns_number_total 7074 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.798 _refine_diff_density_min -0.774 _refine_diff_density_rms 0.065 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 448 _refine_ls_number_reflns 7074 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1786 _refine_ls_R_factor_gt 0.0644 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+2.6676P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1162 _refine_ls_wR_factor_ref 0.1538 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C20B-C15B \\sim C20B-C19B \\sim C19B-C18B \\sim C18B-C17B \\sim C17B-C16B \\sim C16B-C15B with sigma of 0.02 C20A-C15A \\sim C20A-C19A \\sim C19A-C18A \\sim C18A-C17A \\sim C16A-C15A \\sim C17A-C16A with sigma of 0.02 O3-C21B \\sim O3-C21A with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C21A) = Uanis(C21B) 4. Others Fixed Sof: Br2A(0.5) C20B(0.5) H20B(0.5) C15B(0.5) O2A(0.5) C6B(0.5) C16B(0.5) H16B(0.5) C3A(0.5) C14A(0.5) H14A(0.5) H14B(0.5) C17B(0.5) H17B(0.5) C19B(0.5) H19B(0.5) C21A(0.5) H21A(0.5) H21B(0.5) C18A(0.5) C4B(0.5) C32B(0.5) H32A(0.5) H32B(0.5) C33B(0.5) H33A(0.5) H33B(0.5) H33C(0.5) C30A(0.5) H30A(0.5) H30B(0.5) C31B(0.5) H31A(0.5) H31B(0.5) H31C(0.5) C31A(0.5) H31D(0.5) H31E(0.5) H31F(0.5) C30B(0.5) H30C(0.5) H30D(0.5) C4A(0.5) C21B(0.5) H21C(0.5) H21D(0.5) C5B(0.5) C5A(0.5) C33A(0.5) H33D(0.5) H33E(0.5) H33F(0.5) C32A(0.5) H32C(0.5) H32D(0.5) C6A(0.5) C3B(0.5) C14B(0.5) H14C(0.5) H14D(0.5) O2B(0.5) C15A(0.5) C20A(0.5) H20A(0.5) C19A(0.5) H19A(0.5) C18B(0.5) C17A(0.5) H17A(0.5) C16A(0.5) H16A(0.5) Br2B(0.5) 5.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C7(H7A,H7B), C14A(H14A,H14B), C21A(H21A,H21B), C32B(H32A, H32B), C30A(H30A,H30B), C30B(H30C,H30D), C21B(H21C,H21D), C32A(H32C,H32D), C14B(H14C,H14D) 5.b Aromatic/amide H refined with riding coordinates: C9(H9), C26(H26), C27(H27), C24(H24), C20B(H20B), C10(H10), C13(H13), C12(H12), C16B(H16B), C23(H23), C17B(H17B), C19B(H19B), C20A(H20A), C19A(H19A), C17A(H17A), C16A(H16A) 5.c Idealised Me refined as rotating group: C29(H29A,H29B,H29C), C33B(H33A,H33B,H33C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F), C33A(H33D,H33E,H33F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br3 Br 0.03903(7) -0.00544(4) 0.59631(4) 0.1068(3) Uani 1 1 d . . . Br1 Br 1.28337(7) 0.82813(6) 0.72238(4) 0.1104(4) Uani 1 1 d . . . Br2A Br 0.3882(8) 1.0565(5) 0.2130(3) 0.0815(11) Uani 0.50 1 d A 1 . O1 O 0.7409(3) 0.7011(3) 0.61187(15) 0.0559(9) Uani 1 1 d . . . C8 C 0.8600(5) 0.7311(4) 0.6407(2) 0.0495(13) Uani 1 1 d . . . C2 C 0.4600(5) 0.7489(3) 0.5494(2) 0.0504(13) Uani 1 1 d . . . C9 C 0.8640(6) 0.7774(4) 0.6922(2) 0.0569(14) Uani 1 1 d . . . H9 H 0.7829 0.7897 0.7106 0.068 Uiso 1 1 calc . . R C26 C 0.0815(6) 0.1956(4) 0.6292(3) 0.0662(16) Uani 1 1 d . . . H26 H 0.0384 0.1774 0.6618 0.079 Uiso 1 1 calc . . R C27 C 0.1292(6) 0.2915(4) 0.6225(3) 0.0617(15) Uani 1 1 d . . . H27 H 0.1165 0.3381 0.6505 0.074 Uiso 1 1 calc . . R C22 C 0.1950(5) 0.3192(4) 0.5752(3) 0.0531(14) Uani 1 1 d . . . C24 C 0.1617(6) 0.1539(4) 0.5392(3) 0.0642(16) Uani 1 1 d . . . H24 H 0.1718 0.1078 0.5108 0.077 Uiso 1 1 calc . . R O3 O 0.2456(4) 0.4135(3) 0.5693(2) 0.0794(13) Uani 1 1 d . . . C20B C 0.2895(12) 0.9002(8) 0.3698(5) 0.046(4) Uiso 0.50 1 d A 2 . H20B H 0.2171 0.9052 0.3940 0.055 Uiso 0.50 1 calc A 2 R C10 C 0.9921(7) 0.8053(4) 0.7162(3) 0.0681(17) Uani 1 1 d . . . H10 H 0.9968 0.8369 0.7508 0.082 Uiso 1 1 calc . . R C15B C 0.3965(11) 0.8331(11) 0.3819(7) 0.048(4) Uiso 0.50 1 d A 2 . C28 C 0.5161(5) 0.8526(3) 0.5445(2) 0.0518(14) Uani 1 1 d . . . H28A H 0.5205 0.8697 0.5052 0.062 Uiso 1 1 calc . . R H28B H 0.6096 0.8547 0.5609 0.062 Uiso 1 1 calc . . R C11 C 1.1104(7) 0.7866(5) 0.6891(3) 0.0696(19) Uani 1 1 d . . . C7 C 0.6110(5) 0.7230(4) 0.6358(2) 0.0558(14) Uani 1 1 d . . . H7A H 0.6017 0.7938 0.6420 0.067 Uiso 1 1 calc A . R H7B H 0.6035 0.6890 0.6713 0.067 Uiso 1 1 calc . . R C13 C 0.9814(6) 0.7127(4) 0.6139(2) 0.0633(16) Uani 1 1 d . . . H13 H 0.9781 0.6812 0.5792 0.076 Uiso 1 1 calc . . R C1 C 0.5013(5) 0.6870(4) 0.5939(2) 0.0547(14) Uani 1 1 d A . . O2A O 0.439(2) 0.7782(16) 0.4086(7) 0.056(4) Uani 0.50 1 d A 1 . C12 C 1.1071(6) 0.7408(5) 0.6383(3) 0.0730(18) Uani 1 1 d . . . H12 H 1.1887 0.7285 0.6202 0.088 Uiso 1 1 calc . . R C6B C 0.4365(15) 0.6038(11) 0.6106(7) 0.048(4) Uani 0.50 1 d A 2 . C16B C 0.5125(13) 0.8321(9) 0.3498(5) 0.052(3) Uiso 0.50 1 d A 2 . H16B H 0.5878 0.7920 0.3598 0.062 Uiso 0.50 1 calc A 2 R C3A C 0.3844(15) 0.7110(11) 0.4974(6) 0.038(4) Uani 0.50 1 d A 1 . C29 C 0.4276(7) 0.9291(4) 0.5735(3) 0.0817(19) Uani 1 1 d . . . H29A H 0.3362 0.9297 0.5561 0.122 Uiso 1 1 calc A . GR H29B H 0.4686 0.9936 0.5702 0.122 Uiso 1 1 calc . . GR H29C H 0.4222 0.9122 0.6124 0.122 Uiso 1 1 calc . . GR C25 C 0.0987(5) 0.1276(4) 0.5873(3) 0.0644(17) Uani 1 1 d . . . C23 C 0.2103(5) 0.2502(4) 0.5334(2) 0.0584(15) Uani 1 1 d . . . H23 H 0.2538 0.2682 0.5009 0.070 Uiso 1 1 calc A . R C14A C 0.339(2) 0.7755(15) 0.4506(9) 0.046(5) Uiso 0.50 1 d A 1 . H14A H 0.2513 0.7512 0.4344 0.055 Uiso 0.50 1 calc A 1 R H14B H 0.3235 0.8421 0.4645 0.055 Uiso 0.50 1 calc A 1 R C17B C 0.5147(14) 0.8920(10) 0.3022(6) 0.060(4) Uiso 0.50 1 d A 2 . H17B H 0.5917 0.8916 0.2802 0.072 Uiso 0.50 1 calc A 2 R C19B C 0.2888(14) 0.9601(10) 0.3222(6) 0.055(4) Uiso 0.50 1 d A 2 . H19B H 0.2160 1.0035 0.3137 0.065 Uiso 0.50 1 calc A 2 R C21A C 0.3434(11) 0.4397(8) 0.5377(4) 0.054(2) Uani 0.50 1 d A 1 . H21A H 0.3158 0.4237 0.4993 0.065 Uiso 0.50 1 calc A 1 R H21B H 0.4249 0.4005 0.5477 0.065 Uiso 0.50 1 calc A 1 R C18A C 0.4007(13) 0.9671(13) 0.2753(8) 0.063(7) Uiso 0.50 1 d A 1 . C4B C 0.2789(10) 0.6293(7) 0.5309(5) 0.048(3) Uani 0.50 1 d A 2 . C32B C 0.489(2) 0.5402(12) 0.6609(9) 0.057(5) Uani 0.50 1 d A 2 . H32A H 0.5876 0.5503 0.6669 0.069 Uiso 0.50 1 calc A 2 R H32B H 0.4737 0.4707 0.6521 0.069 Uiso 0.50 1 calc A 2 R C33B C 0.4164(18) 0.5651(15) 0.7156(8) 0.097(6) Uani 0.50 1 d A 2 . H33A H 0.3215 0.5440 0.7123 0.146 Uiso 0.50 1 calc A 2 GR H33B H 0.4200 0.6354 0.7219 0.146 Uiso 0.50 1 calc A 2 GR H33C H 0.4626 0.5313 0.7464 0.146 Uiso 0.50 1 calc A 2 GR C30A C 0.2708(18) 0.5690(15) 0.4423(9) 0.074(5) Uani 0.50 1 d A 1 . H30A H 0.2857 0.6140 0.4114 0.088 Uiso 0.50 1 calc A 1 R H30B H 0.3093 0.5050 0.4328 0.088 Uiso 0.50 1 calc A 1 R C31B C 0.202(2) 0.550(2) 0.4410(11) 0.095(9) Uani 0.50 1 d A 2 . H31A H 0.1245 0.5198 0.4208 0.143 Uiso 0.50 1 calc A 2 GR H31B H 0.2705 0.4999 0.4497 0.143 Uiso 0.50 1 calc A 2 GR H31C H 0.2411 0.6003 0.4183 0.143 Uiso 0.50 1 calc A 2 GR C31A C 0.119(2) 0.558(2) 0.4495(11) 0.113(9) Uani 0.50 1 d A 1 . H31D H 0.0755 0.5351 0.4150 0.170 Uiso 0.50 1 calc A 1 GR H31E H 0.0808 0.6210 0.4593 0.170 Uiso 0.50 1 calc A 1 GR H31F H 0.1038 0.5109 0.4787 0.170 Uiso 0.50 1 calc A 1 GR C30B C 0.1551(12) 0.5940(9) 0.4933(5) 0.064(3) Uani 0.50 1 d A 2 . H30C H 0.1024 0.5453 0.5133 0.076 Uiso 0.50 1 calc A 2 R H30D H 0.0948 0.6498 0.4844 0.076 Uiso 0.50 1 calc A 2 R C4A C 0.3469(11) 0.6084(8) 0.4950(5) 0.048(3) Uani 0.50 1 d A 1 . C21B C 0.2360(11) 0.4843(8) 0.5983(4) 0.054(2) Uani 0.50 1 d A 2 . H21C H 0.2663 0.4671 0.6363 0.065 Uiso 0.50 1 calc A 2 R H21D H 0.1397 0.5041 0.5988 0.065 Uiso 0.50 1 calc A 2 R C5B C 0.3229(13) 0.5724(9) 0.5784(6) 0.067(3) Uani 0.50 1 d A 2 . C5A C 0.3823(10) 0.5465(7) 0.5405(4) 0.033(2) Uani 0.50 1 d A 1 . C33A C 0.395(2) 0.5309(12) 0.6825(6) 0.063(4) Uani 0.50 1 d A 1 . H33D H 0.3011 0.5271 0.6677 0.094 Uiso 0.50 1 calc A 1 GR H33E H 0.4118 0.5956 0.6980 0.094 Uiso 0.50 1 calc A 1 GR H33F H 0.4094 0.4817 0.7112 0.094 Uiso 0.50 1 calc A 1 GR C32A C 0.495(2) 0.5118(11) 0.6350(6) 0.048(4) Uani 0.50 1 d A 1 . H32C H 0.5895 0.5234 0.6489 0.058 Uiso 0.50 1 calc A 1 R H32D H 0.4877 0.4431 0.6231 0.058 Uiso 0.50 1 calc A 1 R C6A C 0.4622(16) 0.5787(10) 0.5860(6) 0.038(4) Uani 0.50 1 d A 1 . C3B C 0.3435(14) 0.7185(11) 0.5202(6) 0.034(3) Uani 0.50 1 d A 2 . C14B C 0.3023(14) 0.7834(9) 0.4702(6) 0.046(4) Uani 0.50 1 d A 2 . H14C H 0.2116 0.7644 0.4549 0.055 Uiso 0.50 1 calc A 2 R H14D H 0.2991 0.8525 0.4814 0.055 Uiso 0.50 1 calc A 2 R O2B O 0.4061(18) 0.7690(15) 0.4288(7) 0.051(4) Uani 0.50 1 d A 2 . C15A C 0.4208(12) 0.8397(10) 0.3649(6) 0.049(4) Uiso 0.50 1 d A 1 . C20A C 0.2960(14) 0.8849(9) 0.3511(6) 0.061(5) Uiso 0.50 1 d A 1 . H20A H 0.2185 0.8735 0.3720 0.073 Uiso 0.50 1 calc A 1 R C19A C 0.2897(15) 0.9467(11) 0.3061(6) 0.061(5) Uiso 0.50 1 d A 1 . H19A H 0.2054 0.9762 0.2959 0.074 Uiso 0.50 1 calc A 1 R C18B C 0.4010(12) 0.9527(12) 0.2877(7) 0.052(6) Uiso 0.50 1 d A 2 . C17A C 0.5195(14) 0.9173(10) 0.2869(6) 0.061(4) Uiso 0.50 1 d A 1 . H17A H 0.5949 0.9263 0.2645 0.073 Uiso 0.50 1 calc A 1 R C16A C 0.5294(12) 0.8541(9) 0.3312(5) 0.049(3) Uiso 0.50 1 d A 1 . H16A H 0.6118 0.8201 0.3388 0.059 Uiso 0.50 1 calc A 1 R Br2B Br 0.3988(9) 1.0303(5) 0.2241(3) 0.0852(12) Uani 0.50 1 d 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 Br3 0.0864(5) 0.0407(3) 0.1970(9) 0.0192(5) 0.0490(5) -0.0053(3) Br1 0.0792(5) 0.1256(7) 0.1216(7) 0.0294(5) -0.0508(4) -0.0368(5) Br2A 0.0877(17) 0.097(3) 0.060(2) 0.0351(17) 0.0027(14) -0.017(2) O1 0.039(2) 0.068(2) 0.060(2) -0.0101(19) -0.0002(17) -0.0026(18) C8 0.044(3) 0.046(3) 0.058(4) 0.007(3) -0.009(3) -0.008(3) C2 0.046(3) 0.034(3) 0.070(4) 0.011(3) -0.001(3) -0.001(2) C9 0.067(4) 0.050(3) 0.053(4) 0.003(3) -0.005(3) -0.010(3) C26 0.053(4) 0.063(4) 0.084(5) 0.014(4) 0.017(3) -0.003(3) C27 0.061(4) 0.055(4) 0.069(4) -0.006(3) 0.003(3) -0.001(3) C22 0.052(3) 0.034(3) 0.073(4) 0.002(3) -0.009(3) -0.001(2) C24 0.064(4) 0.036(3) 0.093(5) -0.004(3) 0.015(3) -0.002(3) O3 0.092(3) 0.031(2) 0.114(4) -0.004(2) -0.013(3) -0.009(2) C10 0.088(5) 0.052(3) 0.063(4) 0.011(3) -0.023(4) -0.019(3) C28 0.057(3) 0.036(3) 0.064(4) 0.005(3) 0.009(3) -0.013(2) C11 0.065(4) 0.066(4) 0.075(5) 0.034(4) -0.029(4) -0.023(3) C7 0.048(3) 0.062(4) 0.058(4) 0.014(3) 0.010(3) 0.005(3) C13 0.051(4) 0.076(4) 0.062(4) 0.000(3) -0.007(3) -0.006(3) C1 0.037(3) 0.050(3) 0.077(4) 0.016(3) 0.001(3) -0.005(3) O2A 0.065(9) 0.057(6) 0.049(11) 0.023(8) 0.020(6) 0.002(6) C12 0.047(4) 0.088(5) 0.083(5) 0.023(4) -0.009(3) -0.005(3) C6B 0.029(8) 0.042(8) 0.073(13) -0.001(7) -0.010(8) -0.001(6) C3A 0.041(8) 0.042(7) 0.030(9) 0.011(7) 0.014(6) -0.002(6) C29 0.108(5) 0.047(3) 0.091(5) 0.003(3) 0.026(4) 0.007(3) C25 0.048(3) 0.040(3) 0.106(5) 0.015(3) 0.013(3) 0.001(3) C23 0.060(3) 0.039(3) 0.077(4) 0.005(3) 0.011(3) -0.005(3) C21A 0.060(5) 0.054(5) 0.047(5) 0.009(4) 0.005(4) -0.016(4) C4B 0.034(6) 0.039(6) 0.070(9) -0.005(6) -0.011(6) -0.008(5) C32B 0.044(8) 0.040(9) 0.088(18) 0.009(9) -0.001(11) 0.005(8) C33B 0.082(11) 0.125(16) 0.086(13) 0.049(12) 0.018(11) 0.007(10) C30A 0.078(14) 0.055(9) 0.085(11) 0.011(8) -0.037(12) -0.009(10) C31B 0.051(16) 0.095(16) 0.135(18) -0.036(13) -0.045(17) 0.003(15) C31A 0.103(17) 0.120(18) 0.110(17) 0.040(13) -0.059(16) -0.034(16) C30B 0.052(7) 0.054(7) 0.084(10) -0.007(7) -0.012(7) 0.008(6) C4A 0.050(7) 0.045(6) 0.049(8) 0.001(6) 0.001(6) -0.009(5) C21B 0.060(5) 0.054(5) 0.047(5) 0.009(4) 0.005(4) -0.016(4) C5B 0.062(9) 0.047(7) 0.092(11) 0.023(7) -0.015(8) -0.014(6) C5A 0.040(6) 0.030(5) 0.028(6) 0.001(5) 0.004(5) -0.002(4) C33A 0.091(12) 0.076(10) 0.021(8) 0.011(7) -0.002(8) 0.015(9) C32A 0.070(9) 0.032(8) 0.041(11) 0.002(6) -0.003(8) 0.019(7) C6A 0.039(8) 0.028(7) 0.047(10) 0.000(6) 0.012(7) 0.014(5) C3B 0.033(8) 0.042(6) 0.027(9) 0.012(7) 0.005(6) 0.003(6) C14B 0.046(8) 0.042(7) 0.050(10) -0.008(6) 0.010(7) 0.010(6) O2B 0.052(10) 0.060(7) 0.042(11) 0.022(7) 0.014(7) 0.014(7) Br2B 0.1008(18) 0.086(3) 0.068(3) 0.0290(17) 0.0021(18) -0.0127(19) _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 Br3 C25 1.899(5) . ? Br1 C11 1.905(6) . ? Br2A C18A 1.916(19) . ? O1 C8 1.376(5) . ? O1 C7 1.433(6) . ? C8 C9 1.379(7) . ? C8 C13 1.383(7) . ? C2 C28 1.506(6) . ? C2 C1 1.397(7) . ? C2 C3A 1.504(16) . ? C2 C3B 1.362(15) . ? C9 H9 0.9300 . ? C9 C10 1.394(7) . ? C26 H26 0.9300 . ? C26 C27 1.385(7) . ? C26 C25 1.373(8) . ? C27 H27 0.9300 . ? C27 C22 1.372(7) . ? C22 O3 1.371(6) . ? C22 C23 1.377(7) . ? C24 H24 0.9300 . ? C24 C25 1.369(8) . ? C24 C23 1.389(7) . ? O3 C21A 1.285(9) . ? O3 C21B 1.185(10) . ? C20B H20B 0.9300 . ? C20B C15B 1.395(12) . ? C20B C19B 1.395(12) . ? C10 H10 0.9300 . ? C10 C11 1.362(9) . ? C15B C16B 1.386(13) . ? C15B O2B 1.41(2) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C29 1.525(7) . ? C11 C12 1.361(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C1 1.506(7) . ? C13 H13 0.9300 . ? C13 C12 1.378(7) . ? C1 C6B 1.353(16) . ? C1 C6A 1.518(15) . ? O2A C14A 1.42(2) . ? O2A C15A 1.34(2) . ? C12 H12 0.9300 . ? C6B C32B 1.54(2) . ? C6B C5B 1.38(2) . ? C16B H16B 0.9300 . ? C16B C17B 1.394(13) . ? C3A C14A 1.47(3) . ? C3A C4A 1.430(18) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C23 H23 0.9300 . ? C14A H14A 0.9700 . ? C14A H14B 0.9700 . ? C17B H17B 0.9300 . ? C17B C18B 1.402(12) . ? C19B H19B 0.9300 . ? C19B C18B 1.394(12) . ? C21A H21A 0.9700 . ? C21A H21B 0.9700 . ? C21A C5A 1.488(13) . ? C18A C19A 1.354(13) . ? C18A C17A 1.348(13) . ? C4B C30B 1.542(15) . ? C4B C5B 1.419(15) . ? C4B C3B 1.383(17) . ? C32B H32A 0.9700 . ? C32B H32B 0.9700 . ? C32B C33B 1.54(2) . ? C33B H33A 0.9600 . ? C33B H33B 0.9600 . ? C33B H33C 0.9600 . ? C30A H30A 0.9700 . ? C30A H30B 0.9700 . ? C30A C31A 1.49(3) . ? C30A C4A 1.53(2) . ? C31B H31A 0.9600 . ? C31B H31B 0.9600 . ? C31B H31C 0.9600 . ? C31B C30B 1.47(3) . ? C31A H31D 0.9600 . ? C31A H31E 0.9600 . ? C31A H31F 0.9600 . ? C30B H30C 0.9700 . ? C30B H30D 0.9700 . ? C4A C5A 1.400(13) . ? C21B H21C 0.9700 . ? C21B H21D 0.9700 . ? C21B C5B 1.542(15) . ? C5A C6A 1.377(19) . ? C33A H33D 0.9600 . ? C33A H33E 0.9600 . ? C33A H33F 0.9600 . ? C33A C32A 1.54(2) . ? C32A H32C 0.9700 . ? C32A H32D 0.9700 . ? C32A C6A 1.50(2) . ? C3B C14B 1.52(2) . ? C14B H14C 0.9700 . ? C14B H14D 0.9700 . ? C14B O2B 1.452(19) . ? C15A C20A 1.379(12) . ? C15A C16A 1.363(13) . ? C20A H20A 0.9300 . ? C20A C19A 1.359(12) . ? C19A H19A 0.9300 . ? C18B Br2B 1.844(17) . ? C17A H17A 0.9300 . ? C17A C16A 1.359(13) . ? C16A H16A 0.9300 . ? 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 C8 O1 C7 118.0(4) . . ? O1 C8 C9 124.8(5) . . ? O1 C8 C13 115.1(5) . . ? C9 C8 C13 120.1(5) . . ? C1 C2 C28 121.4(5) . . ? C1 C2 C3A 122.7(7) . . ? C3A C2 C28 114.5(7) . . ? C3B C2 C28 122.1(7) . . ? C3B C2 C1 114.4(7) . . ? C3B C2 C3A 27.5(5) . . ? C8 C9 H9 120.7 . . ? C8 C9 C10 118.7(6) . . ? C10 C9 H9 120.7 . . ? C27 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? C25 C26 C27 119.1(6) . . ? C26 C27 H27 119.4 . . ? C22 C27 C26 121.2(5) . . ? C22 C27 H27 119.4 . . ? C27 C22 C23 118.8(5) . . ? O3 C22 C27 121.1(5) . . ? O3 C22 C23 120.1(6) . . ? C25 C24 H24 120.3 . . ? C25 C24 C23 119.4(5) . . ? C23 C24 H24 120.3 . . ? C21A O3 C22 126.2(7) . . ? C21B O3 C22 130.5(7) . . ? C21B O3 C21A 101.5(7) . . ? C15B C20B H20B 119.3 . . ? C19B C20B H20B 119.3 . . ? C19B C20B C15B 121.5(13) . . ? C9 C10 H10 119.9 . . ? C11 C10 C9 120.3(6) . . ? C11 C10 H10 119.9 . . ? C20B C15B O2B 125.7(12) . . ? C16B C15B C20B 120.1(14) . . ? C16B C15B O2B 114.0(12) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? C2 C28 C29 112.4(4) . . ? H28A C28 H28B 107.9 . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? C10 C11 Br1 119.2(6) . . ? C12 C11 Br1 119.5(6) . . ? C12 C11 C10 121.3(5) . . ? O1 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? O1 C7 C1 105.8(4) . . ? H7A C7 H7B 108.7 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? C8 C13 H13 119.8 . . ? C12 C13 C8 120.4(6) . . ? C12 C13 H13 119.8 . . ? C2 C1 C7 118.9(4) . . ? C2 C1 C6A 114.7(7) . . ? C7 C1 C6A 123.9(7) . . ? C6B C1 C2 126.8(8) . . ? C6B C1 C7 113.2(8) . . ? C6B C1 C6A 28.8(7) . . ? C15A O2A C14A 120(2) . . ? C11 C12 C13 119.2(6) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C1 C6B C32B 123.3(13) . . ? C1 C6B C5B 117.2(13) . . ? C5B C6B C32B 119.4(14) . . ? C15B C16B H16B 120.4 . . ? C15B C16B C17B 119.2(12) . . ? C17B C16B H16B 120.4 . . ? C14A C3A C2 123.2(13) . . ? C4A C3A C2 118.3(11) . . ? C4A C3A C14A 118.3(14) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C25 Br3 120.0(5) . . ? C24 C25 Br3 119.2(5) . . ? C24 C25 C26 120.8(5) . . ? C22 C23 C24 120.7(5) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? O2A C14A C3A 111.0(18) . . ? O2A C14A H14A 109.4 . . ? O2A C14A H14B 109.4 . . ? C3A C14A H14A 109.4 . . ? C3A C14A H14B 109.4 . . ? H14A C14A H14B 108.0 . . ? C16B C17B H17B 120.0 . . ? C16B C17B C18B 120.0(13) . . ? C18B C17B H17B 120.0 . . ? C20B C19B H19B 121.2 . . ? C18B C19B C20B 117.6(12) . . ? C18B C19B H19B 121.2 . . ? O3 C21A H21A 108.4 . . ? O3 C21A H21B 108.4 . . ? O3 C21A C5A 115.5(9) . . ? H21A C21A H21B 107.5 . . ? C5A C21A H21A 108.4 . . ? C5A C21A H21B 108.4 . . ? C19A C18A Br2A 121.6(12) . . ? C17A C18A Br2A 119.8(12) . . ? C17A C18A C19A 118.4(17) . . ? C5B C4B C30B 119.8(9) . . ? C3B C4B C30B 120.4(11) . . ? C3B C4B C5B 119.7(10) . . ? C6B C32B H32A 109.0 . . ? C6B C32B H32B 109.0 . . ? C6B C32B C33B 113.1(13) . . ? H32A C32B H32B 107.8 . . ? C33B C32B H32A 109.0 . . ? C33B C32B H32B 109.0 . . ? C32B C33B H33A 109.5 . . ? C32B C33B H33B 109.5 . . ? C32B C33B H33C 109.5 . . ? H33A C33B H33B 109.5 . . ? H33A C33B H33C 109.5 . . ? H33B C33B H33C 109.5 . . ? H30A C30A H30B 107.9 . . ? C31A C30A H30A 109.1 . . ? C31A C30A H30B 109.1 . . ? C31A C30A C4A 112(2) . . ? C4A C30A H30A 109.1 . . ? C4A C30A H30B 109.1 . . ? H31A C31B H31B 109.5 . . ? H31A C31B H31C 109.5 . . ? H31B C31B H31C 109.5 . . ? C30B C31B H31A 109.5 . . ? C30B C31B H31B 109.5 . . ? C30B C31B H31C 109.5 . . ? C4B C30B H30C 109.4 . . ? C4B C30B H30D 109.4 . . ? C31B C30B C4B 111.2(12) . . ? C31B C30B H30C 109.4 . . ? C31B C30B H30D 109.4 . . ? H30C C30B H30D 108.0 . . ? C3A C4A C30A 118.8(12) . . ? C5A C4A C3A 119.5(10) . . ? C5A C4A C30A 121.7(11) . . ? O3 C21B H21C 109.1 . . ? O3 C21B H21D 109.1 . . ? O3 C21B C5B 112.5(10) . . ? H21C C21B H21D 107.8 . . ? C5B C21B H21C 109.1 . . ? C5B C21B H21D 109.1 . . ? C6B C5B C4B 119.0(11) . . ? C6B C5B C21B 119.6(12) . . ? C4B C5B C21B 121.0(10) . . ? C4A C5A C21A 119.3(9) . . ? C6A C5A C21A 118.2(9) . . ? C6A C5A C4A 122.3(10) . . ? C33A C32A H32C 109.5 . . ? C33A C32A H32D 109.5 . . ? H32C C32A H32D 108.1 . . ? C6A C32A C33A 110.7(13) . . ? C6A C32A H32C 109.5 . . ? C6A C32A H32D 109.5 . . ? C5A C6A C1 122.0(11) . . ? C5A C6A C32A 121.3(13) . . ? C32A C6A C1 115.9(12) . . ? C2 C3B C4B 122.4(11) . . ? C2 C3B C14B 114.3(11) . . ? C4B C3B C14B 122.7(12) . . ? C3B C14B H14C 110.3 . . ? C3B C14B H14D 110.3 . . ? H14C C14B H14D 108.6 . . ? O2B C14B C3B 107.1(12) . . ? O2B C14B H14C 110.3 . . ? O2B C14B H14D 110.3 . . ? C15B O2B C14B 115.8(14) . . ? O2A C15A C20A 122.8(14) . . ? O2A C15A C16A 118.1(14) . . ? C16A C15A C20A 119.0(12) . . ? C15A C20A H20A 121.0 . . ? C19A C20A C15A 117.9(13) . . ? C19A C20A H20A 121.0 . . ? C18A C19A C20A 122.9(15) . . ? C18A C19A H19A 118.5 . . ? C20A C19A H19A 118.5 . . ? C17B C18B Br2B 121.1(11) . . ? C19B C18B C17B 121.2(14) . . ? C19B C18B Br2B 117.7(10) . . ? C18A C17A H17A 119.9 . . ? C18A C17A C16A 120.2(14) . . ? C16A C17A H17A 119.9 . . ? C15A C16A H16A 119.4 . . ? C17A C16A C15A 121.2(12) . . ? C17A C16A H16A 119.4 . . ? 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 Br1 C11 C12 C13 -178.7(4) . . . . ? Br2A C18A C19A C20A -178.9(13) . . . . ? Br2A C18A C17A C16A 179.7(11) . . . . ? O1 C8 C9 C10 -178.9(5) . . . . ? O1 C8 C13 C12 179.1(5) . . . . ? O1 C7 C1 C2 -84.1(6) . . . . ? O1 C7 C1 C6B 107.4(8) . . . . ? O1 C7 C1 C6A 76.8(8) . . . . ? C8 O1 C7 C1 176.8(4) . . . . ? C8 C9 C10 C11 -0.3(8) . . . . ? C8 C13 C12 C11 0.2(9) . . . . ? C2 C1 C6B C32B -179.3(11) . . . . ? C2 C1 C6B C5B 4.6(18) . . . . ? C2 C1 C6A C5A -5.2(14) . . . . ? C2 C1 C6A C32A -175.3(11) . . . . ? C2 C3A C14A O2A 94(2) . . . . ? C2 C3A C4A C30A -179.7(12) . . . . ? C2 C3A C4A C5A -0.6(17) . . . . ? C2 C3B C14B O2B 69.0(16) . . . . ? C9 C8 C13 C12 -0.3(8) . . . . ? C9 C10 C11 Br1 178.8(4) . . . . ? C9 C10 C11 C12 0.2(9) . . . . ? C26 C27 C22 O3 -178.2(5) . . . . ? C26 C27 C22 C23 1.5(8) . . . . ? C27 C26 C25 Br3 178.2(4) . . . . ? C27 C26 C25 C24 -0.2(8) . . . . ? C27 C22 O3 C21A 156.3(8) . . . . ? C27 C22 O3 C21B -5.4(11) . . . . ? C27 C22 C23 C24 -0.7(8) . . . . ? C22 O3 C21A C5A -177.9(6) . . . . ? C22 O3 C21B C5B 173.9(7) . . . . ? O3 C22 C23 C24 178.9(5) . . . . ? O3 C21A C5A C4A -108.3(12) . . . . ? O3 C21A C5A C6A 77.0(13) . . . . ? O3 C21B C5B C6B -112.2(15) . . . . ? O3 C21B C5B C4B 75.3(16) . . . . ? C20B C15B C16B C17B -6.1(17) . . . . ? C20B C15B O2B C14B -7(2) . . . . ? C20B C19B C18B C17B -4(2) . . . . ? C20B C19B C18B Br2B 179.0(11) . . . . ? C10 C11 C12 C13 -0.1(9) . . . . ? C15B C20B C19B C18B -2(2) . . . . ? C15B C16B C17B C18B 0.4(18) . . . . ? C28 C2 C1 C7 -3.9(7) . . . . ? C28 C2 C1 C6B 162.9(9) . . . . ? C28 C2 C1 C6A -166.5(7) . . . . ? C28 C2 C3A C14A -14.3(16) . . . . ? C28 C2 C3A C4A 170.2(9) . . . . ? C28 C2 C3B C4B -169.5(10) . . . . ? C28 C2 C3B C14B 18.4(14) . . . . ? C7 O1 C8 C9 2.8(7) . . . . ? C7 O1 C8 C13 -176.6(4) . . . . ? C7 C1 C6B C32B -11.9(17) . . . . ? C7 C1 C6B C5B 172.1(11) . . . . ? C7 C1 C6A C5A -166.9(9) . . . . ? C7 C1 C6A C32A 23.0(15) . . . . ? C13 C8 C9 C10 0.4(7) . . . . ? C1 C2 C28 C29 -90.5(6) . . . . ? C1 C2 C3A C14A 179.0(12) . . . . ? C1 C2 C3A C4A 3.5(14) . . . . ? C1 C2 C3B C4B -5.3(15) . . . . ? C1 C2 C3B C14B -177.5(9) . . . . ? C1 C6B C32B C33B 96.4(19) . . . . ? C1 C6B C5B C4B -1(2) . . . . ? C1 C6B C5B C21B -174.0(11) . . . . ? O2A C15A C20A C19A 179.4(17) . . . . ? O2A C15A C16A C17A -178.4(15) . . . . ? C6B C1 C6A C5A 117(3) . . . . ? C6B C1 C6A C32A -53(2) . . . . ? C16B C15B O2B C14B 166.9(14) . . . . ? C16B C17B C18B C19B 5(2) . . . . ? C16B C17B C18B Br2B -178.4(11) . . . . ? C3A C2 C28 C29 102.7(8) . . . . ? C3A C2 C1 C7 161.9(7) . . . . ? C3A C2 C1 C6B -31.4(12) . . . . ? C3A C2 C1 C6A -0.7(10) . . . . ? C3A C2 C3B C4B 109(3) . . . . ? C3A C2 C3B C14B -63(2) . . . . ? C3A C4A C5A C21A -179.8(10) . . . . ? C3A C4A C5A C6A -5.4(19) . . . . ? C25 C26 C27 C22 -1.0(8) . . . . ? C25 C24 C23 C22 -0.4(8) . . . . ? C23 C22 O3 C21A -23.4(9) . . . . ? C23 C22 O3 C21B 175.0(8) . . . . ? C23 C24 C25 Br3 -177.5(4) . . . . ? C23 C24 C25 C26 0.9(8) . . . . ? C14A O2A C15A C20A -15(3) . . . . ? C14A O2A C15A C16A 168.0(19) . . . . ? C14A C3A C4A C30A 5(2) . . . . ? C14A C3A C4A C5A -176.3(13) . . . . ? C19B C20B C15B C16B 6.9(19) . . . . ? C19B C20B C15B O2B -179.6(15) . . . . ? C21A O3 C21B C5B 9.0(11) . . . . ? C21A C5A C6A C1 -177.0(9) . . . . ? C21A C5A C6A C32A -7.4(18) . . . . ? C18A C17A C16A C15A -0.2(19) . . . . ? C4B C3B C14B O2B -103.1(16) . . . . ? C32B C6B C5B C4B -177.5(14) . . . . ? C32B C6B C5B C21B 10(2) . . . . ? C30A C4A C5A C21A -0.7(19) . . . . ? C30A C4A C5A C6A 173.7(14) . . . . ? C31A C30A C4A C3A -101.2(19) . . . . ? C31A C30A C4A C5A 80(2) . . . . ? C30B C4B C5B C6B 178.1(13) . . . . ? C30B C4B C5B C21B -9(2) . . . . ? C30B C4B C3B C2 -174.5(10) . . . . ? C30B C4B C3B C14B -3.0(19) . . . . ? C4A C3A C14A O2A -90(2) . . . . ? C4A C5A C6A C1 8.5(19) . . . . ? C4A C5A C6A C32A 178.1(13) . . . . ? C21B O3 C21A C5A -12.1(11) . . . . ? C5B C6B C32B C33B -87.6(19) . . . . ? C5B C4B C30B C31B -103.3(18) . . . . ? C5B C4B C3B C2 8(2) . . . . ? C5B C4B C3B C14B 179.9(13) . . . . ? C33A C32A C6A C1 73.0(17) . . . . ? C33A C32A C6A C5A -97.2(15) . . . . ? C6A C1 C6B C32B 107(3) . . . . ? C6A C1 C6B C5B -69(2) . . . . ? C3B C2 C28 C29 72.6(9) . . . . ? C3B C2 C1 C7 -168.1(7) . . . . ? C3B C2 C1 C6B -1.4(12) . . . . ? C3B C2 C1 C6A 29.2(10) . . . . ? C3B C2 C3A C14A 99(3) . . . . ? C3B C2 C3A C4A -77(2) . . . . ? C3B C4B C30B C31B 79.6(17) . . . . ? C3B C4B C5B C6B -5(2) . . . . ? C3B C4B C5B C21B 167.7(12) . . . . ? C3B C14B O2B C15B -171.9(14) . . . . ? O2B C15B C16B C17B 179.6(14) . . . . ? C15A O2A C14A C3A -174.3(15) . . . . ? C15A C20A C19A C18A -2(2) . . . . ? C20A C15A C16A C17A 4.6(18) . . . . ? C19A C18A C17A C16A -5(2) . . . . ? C17A C18A C19A C20A 6(3) . . . . ? C16A C15A C20A C19A -4(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962415' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Br-gf-298K _audit_creation_date 2013-12-28 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Br-gf, 298 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-bromophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 Br3 O3' _chemical_formula_sum 'C33 H33 Br3 O3' _chemical_formula_weight 717.32 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.6977(5) _cell_length_b 13.4907(7) _cell_length_c 23.9687(19) _cell_angle_alpha 90.00 _cell_angle_beta 92.416(6) _cell_angle_gamma 90.00 _cell_volume 3133.0(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1855 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.0780 _cell_measurement_theta_min 3.7159 _exptl_absorpt_coefficient_mu 3.894 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.55575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1440 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_unetI/netI 0.1136 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 17120 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.14 _diffrn_reflns_theta_min 3.72 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.857 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0448948000 _diffrn_orient_matrix_UB_12 0.0334640000 _diffrn_orient_matrix_UB_13 0.0130788000 _diffrn_orient_matrix_UB_21 0.0297894000 _diffrn_orient_matrix_UB_22 -0.0132904000 _diffrn_orient_matrix_UB_23 0.0264772000 _diffrn_orient_matrix_UB_31 0.0495868000 _diffrn_orient_matrix_UB_32 0.0383064000 _diffrn_orient_matrix_UB_33 -0.0022178000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2772 _reflns_number_total 7244 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.575 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.064 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 377 _refine_ls_number_reflns 7244 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.2023 _refine_ls_R_factor_gt 0.0701 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0723P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1436 _refine_ls_wR_factor_ref 0.1989 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C20A-C15A \\sim C20A-C19A \\sim C19A-C18A \\sim C18A-C17A \\sim C16A-C15A \\sim C17A-C16A with sigma of 0.02 C20B-C15B \\sim C20B-C19B \\sim C19B-C18B \\sim C18B-C17B \\sim C17B-C16B \\sim C16B-C15B with sigma of 0.02 O3-C21B \\sim O3-C21A with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C5B) = Uanis(C5A) Uanis(C21B) = Uanis(C21A) 4. Others Fixed Sof: Br2A(0.5) C20B(0.5) H20B(0.5) C15B(0.5) O2A(0.5) C6B(0.5) C16B(0.5) H16B(0.5) C3A(0.5) C14A(0.5) H14A(0.5) H14B(0.5) C17B(0.5) H17B(0.5) C19B(0.5) H19B(0.5) C21A(0.5) H21A(0.5) H21B(0.5) C18A(0.5) C4B(0.5) C32B(0.5) H32A(0.5) H32B(0.5) C33B(0.5) H33A(0.5) H33B(0.5) H33C(0.5) C30A(0.5) H30A(0.5) H30B(0.5) C31B(0.5) H31A(0.5) H31B(0.5) H31C(0.5) C31A(0.5) H31D(0.5) H31E(0.5) H31F(0.5) C30B(0.5) H30C(0.5) H30D(0.5) C4A(0.5) C21B(0.5) H21C(0.5) H21D(0.5) C5B(0.5) C5A(0.5) C33A(0.5) H33D(0.5) H33E(0.5) H33F(0.5) C32A(0.5) H32C(0.5) H32D(0.5) C6A(0.5) C3B(0.5) C14B(0.5) H14C(0.5) H14D(0.5) O2B(0.5) C15A(0.5) C20A(0.5) H20A(0.5) C19A(0.5) H19A(0.5) C18B(0.5) C17A(0.5) H17A(0.5) C16A(0.5) H16A(0.5) Br2B(0.5) 5.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C7(H7A,H7B), C14A(H14A,H14B), C21A(H21A,H21B), C32B(H32A, H32B), C30A(H30A,H30B), C30B(H30C,H30D), C21B(H21C,H21D), C32A(H32C,H32D), C14B(H14C,H14D) 5.b Aromatic/amide H refined with riding coordinates: C9(H9), C26(H26), C27(H27), C24(H24), C20B(H20B), C10(H10), C13(H13), C12(H12), C16B(H16B), C23(H23), C17B(H17B), C19B(H19B), C20A(H20A), C19A(H19A), C17A(H17A), C16A(H16A) 5.c Idealised Me refined as rotating group: C29(H29A,H29B,H29C), C33B(H33A,H33B,H33C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F), C33A(H33D,H33E,H33F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Br3 Br 0.03932(9) -0.00459(5) 0.59644(5) 0.1243(4) Uani 1 1 d . . . Br1 Br 1.28064(8) 0.82727(7) 0.72162(4) 0.1160(4) Uani 1 1 d . . . Br2A Br 0.3871(11) 1.0558(7) 0.2158(5) 0.0946(15) Uani 0.50 1 d A 1 . O1 O 0.7401(4) 0.7005(3) 0.61145(17) 0.0662(11) Uani 1 1 d . . . C8 C 0.8583(6) 0.7310(4) 0.6401(3) 0.0562(15) Uani 1 1 d . . . C2 C 0.4603(6) 0.7485(4) 0.5494(3) 0.0588(16) Uani 1 1 d . . . C9 C 0.8628(6) 0.7765(4) 0.6910(3) 0.0613(16) Uani 1 1 d . . . H9 H 0.7817 0.7886 0.7093 0.074 Uiso 1 1 calc . . R C26 C 0.0811(6) 0.1949(5) 0.6292(3) 0.081(2) Uani 1 1 d . . . H26 H 0.0376 0.1763 0.6614 0.098 Uiso 1 1 calc . . R C27 C 0.1294(6) 0.2921(5) 0.6229(3) 0.0724(18) Uani 1 1 d . . . H27 H 0.1171 0.3383 0.6511 0.087 Uiso 1 1 calc . . R C22 C 0.1947(6) 0.3198(4) 0.5757(3) 0.0611(16) Uani 1 1 d . . . C24 C 0.1622(7) 0.1553(4) 0.5398(3) 0.079(2) Uani 1 1 d . . . H24 H 0.1735 0.1098 0.5112 0.095 Uiso 1 1 calc . . R O3 O 0.2439(5) 0.4138(3) 0.5705(2) 0.0959(16) Uani 1 1 d . . . C20B C 0.2929(14) 0.9029(10) 0.3701(6) 0.060(5) Uiso 0.50 1 d A 2 . H20B H 0.2224 0.9097 0.3950 0.072 Uiso 0.50 1 calc A 2 R C10 C 0.9892(8) 0.8047(5) 0.7154(3) 0.0744(19) Uani 1 1 d . . . H10 H 0.9931 0.8363 0.7499 0.089 Uiso 1 1 calc . . R C15B C 0.3971(13) 0.8321(12) 0.3815(7) 0.058(5) Uiso 0.50 1 d A 2 . C28 C 0.5159(6) 0.8524(4) 0.5444(3) 0.0611(16) Uani 1 1 d . . . H28A H 0.5199 0.8696 0.5052 0.073 Uiso 1 1 calc . . R H28B H 0.6091 0.8547 0.5607 0.073 Uiso 1 1 calc . . R C11 C 1.1078(7) 0.7858(5) 0.6885(3) 0.0712(18) Uani 1 1 d . . . C7 C 0.6099(6) 0.7218(5) 0.6351(3) 0.0644(16) Uani 1 1 d . . . H7A H 0.6002 0.7925 0.6414 0.077 Uiso 1 1 calc A . R H7B H 0.6022 0.6876 0.6704 0.077 Uiso 1 1 calc . . R C13 C 0.9799(6) 0.7130(5) 0.6137(3) 0.0734(18) Uani 1 1 d . . . H13 H 0.9769 0.6819 0.5791 0.088 Uiso 1 1 calc . . R C1 C 0.5024(5) 0.6861(4) 0.5935(3) 0.0595(16) Uani 1 1 d A . . O2A O 0.4366(12) 0.7756(9) 0.4102(6) 0.078(5) Uiso 0.50 1 d A 1 . C12 C 1.1054(6) 0.7404(5) 0.6381(3) 0.0782(19) Uani 1 1 d . . . H12 H 1.1869 0.7280 0.6202 0.094 Uiso 1 1 calc . . R C6B C 0.4388(13) 0.6023(10) 0.6089(6) 0.059(4) Uiso 0.50 1 d A 2 . C16B C 0.5117(15) 0.8310(11) 0.3484(6) 0.065(4) Uiso 0.50 1 d A 2 . H16B H 0.5855 0.7893 0.3575 0.078 Uiso 0.50 1 calc A 2 R C3A C 0.382(2) 0.7095(16) 0.4980(7) 0.048(4) Uani 0.50 1 d A 1 . C29 C 0.4277(8) 0.9281(4) 0.5734(3) 0.093(2) Uani 1 1 d . . . H29A H 0.3352 0.9260 0.5575 0.140 Uiso 1 1 calc A . GR H29B H 0.4655 0.9932 0.5684 0.140 Uiso 1 1 calc . . GR H29C H 0.4267 0.9131 0.6125 0.140 Uiso 1 1 calc . . GR C25 C 0.0990(6) 0.1278(5) 0.5872(4) 0.075(2) Uani 1 1 d . . . C23 C 0.2094(6) 0.2517(4) 0.5348(3) 0.0659(16) Uani 1 1 d . . . H23 H 0.2523 0.2703 0.5024 0.079 Uiso 1 1 calc A . R C14A C 0.337(2) 0.7743(11) 0.4506(8) 0.066(5) Uiso 0.50 1 d A 1 . H14A H 0.2507 0.7502 0.4342 0.080 Uiso 0.50 1 calc A 1 R H14B H 0.3229 0.8411 0.4641 0.080 Uiso 0.50 1 calc A 1 R C17B C 0.5162(18) 0.8926(12) 0.3014(7) 0.070(5) Uiso 0.50 1 d A 2 . H17B H 0.5941 0.8935 0.2800 0.084 Uiso 0.50 1 calc A 2 R C19B C 0.2919(18) 0.9632(12) 0.3227(7) 0.072(6) Uiso 0.50 1 d A 2 . H19B H 0.2212 1.0085 0.3151 0.086 Uiso 0.50 1 calc A 2 R C21A C 0.3422(13) 0.4409(9) 0.5387(5) 0.066(2) Uani 0.50 1 d A 1 . H21A H 0.3149 0.4242 0.5004 0.080 Uiso 0.50 1 calc A 1 R H21B H 0.4236 0.4021 0.5488 0.080 Uiso 0.50 1 calc A 1 R C18A C 0.3992(17) 0.9651(19) 0.2784(11) 0.076(11) Uiso 0.50 1 d A 1 . C4B C 0.2804(12) 0.6276(8) 0.5280(6) 0.054(3) Uani 0.50 1 d A 2 . C32B C 0.4831(16) 0.5391(11) 0.6617(7) 0.072(4) Uiso 0.50 1 d A 2 . H32A H 0.4625 0.4700 0.6539 0.087 Uiso 0.50 1 calc A 2 R H32B H 0.5823 0.5448 0.6680 0.087 Uiso 0.50 1 calc A 2 R C33B C 0.4163(18) 0.5675(14) 0.7134(7) 0.107(6) Uiso 0.50 1 d A 2 . H33A H 0.3183 0.5591 0.7084 0.161 Uiso 0.50 1 calc A 2 GR H33B H 0.4367 0.6356 0.7218 0.161 Uiso 0.50 1 calc A 2 GR H33C H 0.4504 0.5263 0.7435 0.161 Uiso 0.50 1 calc A 2 GR C30A C 0.266(2) 0.5679(15) 0.4412(8) 0.101(6) Uiso 0.50 1 d A 1 . H30A H 0.2756 0.6133 0.4103 0.122 Uiso 0.50 1 calc A 1 R H30B H 0.3012 0.5035 0.4308 0.122 Uiso 0.50 1 calc A 1 R C31B C 0.197(3) 0.5507(16) 0.4391(9) 0.112(7) Uiso 0.50 1 d A 2 . H31A H 0.1239 0.5590 0.4113 0.168 Uiso 0.50 1 calc A 2 GR H31B H 0.2148 0.4813 0.4447 0.168 Uiso 0.50 1 calc A 2 GR H31C H 0.2791 0.5824 0.4267 0.168 Uiso 0.50 1 calc A 2 GR C31A C 0.122(2) 0.5604(16) 0.4558(10) 0.128(7) Uiso 0.50 1 d A 1 . H31D H 0.0700 0.5280 0.4262 0.191 Uiso 0.50 1 calc A 1 GR H31E H 0.0854 0.6256 0.4614 0.191 Uiso 0.50 1 calc A 1 GR H31F H 0.1160 0.5226 0.4896 0.191 Uiso 0.50 1 calc A 1 GR C30B C 0.1577(14) 0.5950(11) 0.4911(6) 0.076(4) Uiso 0.50 1 d A 2 . H30C H 0.1039 0.5474 0.5114 0.091 Uiso 0.50 1 calc A 2 R H30D H 0.0993 0.6520 0.4829 0.091 Uiso 0.50 1 calc A 2 R C4A C 0.3474(14) 0.6084(10) 0.4960(6) 0.058(3) Uani 0.50 1 d A 1 . C21B C 0.2341(13) 0.4840(9) 0.5989(5) 0.066(2) Uani 0.50 1 d A 2 . H21C H 0.2648 0.4681 0.6369 0.080 Uiso 0.50 1 calc A 2 R H21D H 0.1383 0.5046 0.5993 0.080 Uiso 0.50 1 calc A 2 R C5B C 0.3249(13) 0.5709(9) 0.5760(6) 0.061(3) Uani 0.50 1 d A 2 . C5A C 0.3814(13) 0.5482(9) 0.5405(6) 0.061(3) Uani 0.50 1 d A 1 . C33A C 0.3942(14) 0.5283(9) 0.6848(6) 0.062(3) Uiso 0.50 1 d A 1 . H33D H 0.3005 0.5224 0.6705 0.093 Uiso 0.50 1 calc A 1 GR H33E H 0.4080 0.5928 0.7010 0.093 Uiso 0.50 1 calc A 1 GR H33F H 0.4124 0.4785 0.7127 0.093 Uiso 0.50 1 calc A 1 GR C32A C 0.4958(11) 0.5139(8) 0.6354(5) 0.047(3) Uiso 0.50 1 d A 1 . H32C H 0.5894 0.5268 0.6493 0.056 Uiso 0.50 1 calc A 1 R H32D H 0.4913 0.4455 0.6230 0.056 Uiso 0.50 1 calc A 1 R C6A C 0.4633(11) 0.5812(8) 0.5855(5) 0.039(3) Uiso 0.50 1 d A 1 . C3B C 0.3462(19) 0.7199(14) 0.5203(7) 0.041(4) Uani 0.50 1 d A 2 . C14B C 0.3023(13) 0.7835(10) 0.4694(6) 0.053(4) Uiso 0.50 1 d A 2 . H14C H 0.2128 0.7621 0.4544 0.064 Uiso 0.50 1 calc A 2 R H14D H 0.2956 0.8525 0.4803 0.064 Uiso 0.50 1 calc A 2 R O2B O 0.4064(16) 0.7719(8) 0.4273(6) 0.068(4) Uiso 0.50 1 d A 2 . C15A C 0.4206(13) 0.8410(11) 0.3656(7) 0.058(5) Uiso 0.50 1 d A 1 . C20A C 0.2933(14) 0.8821(10) 0.3522(6) 0.063(5) Uiso 0.50 1 d A 1 . H20A H 0.2154 0.8676 0.3721 0.076 Uiso 0.50 1 calc A 1 R C19A C 0.2895(17) 0.9449(12) 0.3085(6) 0.067(6) Uiso 0.50 1 d A 1 . H19A H 0.2062 0.9757 0.2986 0.080 Uiso 0.50 1 calc A 1 R C18B C 0.4025(15) 0.9528(17) 0.2868(10) 0.064(10) Uiso 0.50 1 d A 2 . C17A C 0.5173(18) 0.9165(13) 0.2873(7) 0.076(6) Uiso 0.50 1 d A 1 . H17A H 0.5899 0.9239 0.2635 0.091 Uiso 0.50 1 calc A 1 R C16A C 0.5279(15) 0.8561(12) 0.3321(6) 0.068(4) Uiso 0.50 1 d A 1 . H16A H 0.6111 0.8238 0.3403 0.081 Uiso 0.50 1 calc A 1 R Br2B Br 0.4012(13) 1.0283(7) 0.2228(5) 0.1051(19) Uani 0.50 1 d 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 Br3 0.0989(6) 0.0518(5) 0.2261(12) 0.0238(5) 0.0554(6) -0.0063(4) Br1 0.0810(5) 0.1362(8) 0.1266(8) 0.0163(6) -0.0449(5) -0.0279(5) Br2A 0.100(2) 0.108(5) 0.076(2) 0.031(3) 0.0068(18) -0.010(3) O1 0.048(2) 0.082(3) 0.068(3) -0.013(2) 0.001(2) -0.004(2) C8 0.050(3) 0.055(3) 0.063(4) 0.010(3) -0.005(3) -0.009(3) C2 0.053(3) 0.038(3) 0.085(5) 0.007(3) -0.006(3) -0.004(3) C9 0.064(4) 0.061(4) 0.058(4) -0.003(3) -0.005(3) -0.010(3) C26 0.067(4) 0.075(5) 0.102(6) 0.022(4) 0.015(4) 0.000(4) C27 0.070(4) 0.062(4) 0.085(5) -0.008(4) 0.003(4) 0.002(3) C22 0.058(4) 0.046(4) 0.078(5) 0.001(3) -0.004(4) -0.002(3) C24 0.080(4) 0.044(4) 0.116(6) -0.006(4) 0.019(4) -0.007(3) O3 0.113(4) 0.034(2) 0.138(5) -0.006(3) -0.018(4) -0.008(3) C10 0.090(5) 0.066(4) 0.066(5) 0.007(3) -0.017(4) -0.008(4) C28 0.065(4) 0.046(3) 0.072(4) 0.004(3) 0.006(3) -0.004(3) C11 0.071(5) 0.071(4) 0.070(5) 0.021(4) -0.021(4) -0.012(4) C7 0.057(4) 0.076(4) 0.060(4) 0.004(3) 0.005(3) 0.001(3) C13 0.062(4) 0.094(5) 0.064(4) -0.007(4) -0.005(4) -0.008(4) C1 0.049(3) 0.047(3) 0.082(5) 0.018(3) -0.007(3) -0.006(3) C12 0.058(4) 0.093(5) 0.083(6) 0.017(4) -0.008(4) -0.002(4) C3A 0.068(12) 0.048(9) 0.030(10) 0.000(9) 0.001(8) 0.010(8) C29 0.120(6) 0.047(4) 0.114(6) 0.004(4) 0.022(5) 0.006(4) C25 0.054(4) 0.049(4) 0.122(7) 0.005(4) 0.016(4) -0.001(3) C23 0.069(4) 0.047(4) 0.083(5) 0.005(4) 0.012(3) -0.003(3) C21A 0.072(6) 0.068(6) 0.060(6) 0.016(5) 0.010(5) -0.015(5) C4B 0.043(7) 0.032(6) 0.085(11) -0.004(7) -0.025(7) 0.000(6) C4A 0.059(8) 0.054(9) 0.062(10) -0.003(7) -0.001(7) -0.009(7) C21B 0.072(6) 0.068(6) 0.060(6) 0.016(5) 0.010(5) -0.015(5) C5B 0.070(7) 0.042(5) 0.070(8) 0.011(6) -0.007(5) -0.010(5) C5A 0.070(7) 0.042(5) 0.070(8) 0.011(6) -0.007(5) -0.010(5) C3B 0.055(10) 0.037(7) 0.031(10) -0.004(8) 0.008(7) 0.005(7) Br2B 0.118(3) 0.101(4) 0.096(4) 0.028(3) -0.002(2) -0.011(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 Br3 C25 1.893(6) . ? Br1 C11 1.908(6) . ? Br2A C18A 1.94(3) . ? O1 C8 1.374(6) . ? O1 C7 1.434(6) . ? C8 C9 1.366(8) . ? C8 C13 1.383(8) . ? C2 C28 1.509(7) . ? C2 C1 1.400(7) . ? C2 C3A 1.51(2) . ? C2 C3B 1.34(2) . ? C9 H9 0.9300 . ? C9 C10 1.389(8) . ? C26 H26 0.9300 . ? C26 C27 1.403(9) . ? C26 C25 1.371(9) . ? C27 H27 0.9300 . ? C27 C22 1.372(8) . ? C22 O3 1.362(7) . ? C22 C23 1.356(8) . ? C24 H24 0.9300 . ? C24 C25 1.364(9) . ? C24 C23 1.387(8) . ? O3 C21A 1.298(10) . ? O3 C21B 1.173(11) . ? C20B H20B 0.9300 . ? C20B C15B 1.409(13) . ? C20B C19B 1.398(13) . ? C10 H10 0.9300 . ? C10 C11 1.366(9) . ? C15B C16B 1.392(14) . ? C15B O2B 1.37(2) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C29 1.519(8) . ? C11 C12 1.355(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C1 1.492(7) . ? C13 H13 0.9300 . ? C13 C12 1.378(8) . ? C1 C6B 1.346(13) . ? C1 C6A 1.475(12) . ? O2A C14A 1.39(2) . ? O2A C15A 1.39(2) . ? C12 H12 0.9300 . ? C6B C32B 1.570(18) . ? C6B C5B 1.397(17) . ? C16B H16B 0.9300 . ? C16B C17B 1.403(15) . ? C3A C14A 1.48(2) . ? C3A C4A 1.41(2) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C23 H23 0.9300 . ? C14A H14A 0.9700 . ? C14A H14B 0.9700 . ? C17B H17B 0.9300 . ? C17B C18B 1.401(14) . ? C19B H19B 0.9300 . ? C19B C18B 1.411(14) . ? C21A H21A 0.9700 . ? C21A H21B 0.9700 . ? C21A C5A 1.497(16) . ? C18A C19A 1.338(14) . ? C18A C17A 1.329(14) . ? C4B C30B 1.517(17) . ? C4B C5B 1.433(17) . ? C4B C3B 1.41(2) . ? C32B H32A 0.9700 . ? C32B H32B 0.9700 . ? C32B C33B 1.47(2) . ? C33B H33A 0.9600 . ? C33B H33B 0.9600 . ? C33B H33C 0.9600 . ? C30A H30A 0.9700 . ? C30A H30B 0.9700 . ? C30A C31A 1.46(3) . ? C30A C4A 1.60(2) . ? C31B H31A 0.9600 . ? C31B H31B 0.9600 . ? C31B H31C 0.9600 . ? C31B C30B 1.45(3) . ? C31A H31D 0.9600 . ? C31A H31E 0.9600 . ? C31A H31F 0.9600 . ? C30B H30C 0.9700 . ? C30B H30D 0.9700 . ? C4A C5A 1.370(18) . ? C21B H21C 0.9700 . ? C21B H21D 0.9700 . ? C21B C5B 1.580(17) . ? C5A C6A 1.386(16) . ? C33A H33D 0.9600 . ? C33A H33E 0.9600 . ? C33A H33F 0.9600 . ? C33A C32A 1.584(18) . ? C32A H32C 0.9700 . ? C32A H32D 0.9700 . ? C32A C6A 1.522(15) . ? C3B C14B 1.54(2) . ? C14B H14C 0.9700 . ? C14B H14D 0.9700 . ? C14B O2B 1.47(2) . ? C15A C20A 1.379(12) . ? C15A C16A 1.356(14) . ? C20A H20A 0.9300 . ? C20A C19A 1.347(13) . ? C19A H19A 0.9300 . ? C18B Br2B 1.84(2) . ? C17A H17A 0.9300 . ? C17A C16A 1.350(15) . ? C16A H16A 0.9300 . ? 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 C8 O1 C7 118.1(4) . . ? O1 C8 C13 115.4(6) . . ? C9 C8 O1 125.2(5) . . ? C9 C8 C13 119.4(5) . . ? C28 C2 C3A 115.3(9) . . ? C1 C2 C28 121.7(5) . . ? C1 C2 C3A 121.8(9) . . ? C3B C2 C28 121.1(9) . . ? C3B C2 C1 115.4(9) . . ? C3B C2 C3A 26.0(7) . . ? C8 C9 H9 120.2 . . ? C8 C9 C10 119.6(6) . . ? C10 C9 H9 120.2 . . ? C27 C26 H26 120.5 . . ? C25 C26 H26 120.5 . . ? C25 C26 C27 119.0(7) . . ? C26 C27 H27 119.6 . . ? C22 C27 C26 120.8(6) . . ? C22 C27 H27 119.6 . . ? O3 C22 C27 120.3(6) . . ? C23 C22 C27 118.6(6) . . ? C23 C22 O3 121.1(6) . . ? C25 C24 H24 120.3 . . ? C25 C24 C23 119.3(6) . . ? C23 C24 H24 120.3 . . ? C21A O3 C22 125.8(8) . . ? C21B O3 C22 131.4(9) . . ? C21B O3 C21A 101.1(9) . . ? C15B C20B H20B 118.9 . . ? C19B C20B H20B 118.9 . . ? C19B C20B C15B 122.1(15) . . ? C9 C10 H10 120.1 . . ? C11 C10 C9 119.7(6) . . ? C11 C10 H10 120.1 . . ? C16B C15B C20B 118.7(15) . . ? O2B C15B C20B 125.5(13) . . ? O2B C15B C16B 115.1(14) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? C2 C28 C29 112.3(5) . . ? H28A C28 H28B 107.9 . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? C10 C11 Br1 119.4(6) . . ? C12 C11 Br1 119.0(6) . . ? C12 C11 C10 121.5(6) . . ? O1 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? O1 C7 C1 105.8(5) . . ? H7A C7 H7B 108.7 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? C8 C13 H13 119.5 . . ? C12 C13 C8 121.0(6) . . ? C12 C13 H13 119.5 . . ? C2 C1 C7 118.9(5) . . ? C2 C1 C6A 114.4(6) . . ? C6B C1 C2 126.1(7) . . ? C6B C1 C7 113.8(7) . . ? C6B C1 C6A 27.4(6) . . ? C6A C1 C7 124.5(6) . . ? C15A O2A C14A 119.0(12) . . ? C11 C12 C13 118.7(7) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C1 C6B C32B 124.3(11) . . ? C1 C6B C5B 117.4(10) . . ? C5B C6B C32B 118.3(11) . . ? C15B C16B H16B 119.8 . . ? C15B C16B C17B 120.3(13) . . ? C17B C16B H16B 119.8 . . ? C14A C3A C2 122.6(16) . . ? C4A C3A C2 118.4(14) . . ? C4A C3A C14A 119.0(16) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C25 Br3 119.2(6) . . ? C24 C25 Br3 120.3(6) . . ? C24 C25 C26 120.5(6) . . ? C22 C23 C24 121.8(6) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? O2A C14A C3A 110.6(16) . . ? O2A C14A H14A 109.5 . . ? O2A C14A H14B 109.5 . . ? C3A C14A H14A 109.5 . . ? C3A C14A H14B 109.5 . . ? H14A C14A H14B 108.1 . . ? C16B C17B H17B 120.2 . . ? C18B C17B C16B 119.5(16) . . ? C18B C17B H17B 120.2 . . ? C20B C19B H19B 121.3 . . ? C20B C19B C18B 117.3(16) . . ? C18B C19B H19B 121.3 . . ? O3 C21A H21A 108.1 . . ? O3 C21A H21B 108.1 . . ? O3 C21A C5A 116.6(10) . . ? H21A C21A H21B 107.3 . . ? C5A C21A H21A 108.1 . . ? C5A C21A H21B 108.1 . . ? C19A C18A Br2A 121.5(15) . . ? C17A C18A Br2A 117.3(14) . . ? C17A C18A C19A 121(2) . . ? C5B C4B C30B 121.0(11) . . ? C3B C4B C30B 121.8(12) . . ? C3B C4B C5B 116.9(12) . . ? C6B C32B H32A 108.5 . . ? C6B C32B H32B 108.5 . . ? H32A C32B H32B 107.5 . . ? C33B C32B C6B 114.9(13) . . ? C33B C32B H32A 108.5 . . ? C33B C32B H32B 108.5 . . ? C32B C33B H33A 109.5 . . ? C32B C33B H33B 109.5 . . ? C32B C33B H33C 109.5 . . ? H33A C33B H33B 109.5 . . ? H33A C33B H33C 109.5 . . ? H33B C33B H33C 109.5 . . ? H30A C30A H30B 108.7 . . ? C31A C30A H30A 110.6 . . ? C31A C30A H30B 110.6 . . ? C31A C30A C4A 105.8(15) . . ? C4A C30A H30A 110.6 . . ? C4A C30A H30B 110.6 . . ? H31A C31B H31B 109.5 . . ? H31A C31B H31C 109.5 . . ? H31B C31B H31C 109.5 . . ? C30B C31B H31A 109.5 . . ? C30B C31B H31B 109.5 . . ? C30B C31B H31C 109.5 . . ? C4B C30B H30C 109.0 . . ? C4B C30B H30D 109.0 . . ? C31B C30B C4B 113.0(16) . . ? C31B C30B H30C 109.0 . . ? C31B C30B H30D 109.0 . . ? H30C C30B H30D 107.8 . . ? C3A C4A C30A 118.0(14) . . ? C5A C4A C3A 120.0(13) . . ? C5A C4A C30A 122.1(12) . . ? O3 C21B H21C 109.7 . . ? O3 C21B H21D 109.7 . . ? O3 C21B C5B 109.6(10) . . ? H21C C21B H21D 108.2 . . ? C5B C21B H21C 109.7 . . ? C5B C21B H21D 109.7 . . ? C6B C5B C4B 119.8(11) . . ? C6B C5B C21B 117.8(11) . . ? C4B C5B C21B 121.5(11) . . ? C4A C5A C21A 119.9(12) . . ? C4A C5A C6A 121.8(11) . . ? C6A C5A C21A 118.0(11) . . ? C33A C32A H32C 108.9 . . ? C33A C32A H32D 108.9 . . ? H32C C32A H32D 107.7 . . ? C6A C32A C33A 113.5(9) . . ? C6A C32A H32C 108.9 . . ? C6A C32A H32D 108.9 . . ? C1 C6A C32A 115.2(9) . . ? C5A C6A C1 123.0(9) . . ? C5A C6A C32A 120.8(10) . . ? C2 C3B C4B 123.6(15) . . ? C2 C3B C14B 116.6(14) . . ? C4B C3B C14B 118.9(15) . . ? C3B C14B H14C 110.1 . . ? C3B C14B H14D 110.1 . . ? H14C C14B H14D 108.4 . . ? O2B C14B C3B 108.1(10) . . ? O2B C14B H14C 110.1 . . ? O2B C14B H14D 110.1 . . ? C15B O2B C14B 117.8(12) . . ? C20A C15A O2A 120.2(13) . . ? C16A C15A O2A 119.1(13) . . ? C16A C15A C20A 120.3(14) . . ? C15A C20A H20A 122.3 . . ? C19A C20A C15A 115.4(15) . . ? C19A C20A H20A 122.3 . . ? C18A C19A C20A 123.5(19) . . ? C18A C19A H19A 118.3 . . ? C20A C19A H19A 118.3 . . ? C17B C18B C19B 121.1(18) . . ? C17B C18B Br2B 120.4(13) . . ? C19B C18B Br2B 118.3(12) . . ? C18A C17A H17A 121.2 . . ? C18A C17A C16A 117.5(18) . . ? C16A C17A H17A 121.2 . . ? C15A C16A H16A 119.1 . . ? C17A C16A C15A 121.8(14) . . ? C17A C16A H16A 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 C11 C12 C13 -178.3(5) . . . . ? Br2A C18A C19A C20A 179.9(16) . . . . ? Br2A C18A C17A C16A 177.6(15) . . . . ? O1 C8 C9 C10 -179.3(5) . . . . ? O1 C8 C13 C12 179.7(5) . . . . ? O1 C7 C1 C2 -84.7(6) . . . . ? O1 C7 C1 C6B 106.6(8) . . . . ? O1 C7 C1 C6A 77.4(8) . . . . ? C8 O1 C7 C1 176.6(4) . . . . ? C8 C9 C10 C11 -0.6(9) . . . . ? C8 C13 C12 C11 -0.1(10) . . . . ? C2 C1 C6B C32B -174.9(11) . . . . ? C2 C1 C6B C5B 4.1(17) . . . . ? C2 C1 C6A C5A -5.5(14) . . . . ? C2 C1 C6A C32A -174.4(8) . . . . ? C2 C3A C14A O2A 92.5(16) . . . . ? C2 C3A C4A C30A -179.4(12) . . . . ? C2 C3A C4A C5A 2(2) . . . . ? C2 C3B C14B O2B 67.3(14) . . . . ? C9 C8 C13 C12 -0.1(9) . . . . ? C9 C10 C11 Br1 178.7(4) . . . . ? C9 C10 C11 C12 0.4(10) . . . . ? C26 C27 C22 O3 -178.6(5) . . . . ? C26 C27 C22 C23 1.1(9) . . . . ? C27 C26 C25 Br3 178.0(4) . . . . ? C27 C26 C25 C24 -0.3(10) . . . . ? C27 C22 O3 C21A 156.4(9) . . . . ? C27 C22 O3 C21B -5.8(12) . . . . ? C27 C22 C23 C24 -0.9(9) . . . . ? C22 O3 C21A C5A -178.8(8) . . . . ? C22 O3 C21B C5B 174.1(7) . . . . ? O3 C22 C23 C24 178.8(5) . . . . ? O3 C21A C5A C4A -108.2(15) . . . . ? O3 C21A C5A C6A 77.9(15) . . . . ? O3 C21B C5B C6B -113.7(13) . . . . ? O3 C21B C5B C4B 76.9(16) . . . . ? C20B C15B C16B C17B -6(2) . . . . ? C20B C15B O2B C14B -2(2) . . . . ? C20B C19B C18B C17B -7(3) . . . . ? C20B C19B C18B Br2B 178.1(15) . . . . ? C10 C11 C12 C13 0.0(10) . . . . ? C15B C20B C19B C18B -2(3) . . . . ? C15B C16B C17B C18B -2(2) . . . . ? C28 C2 C1 C7 -3.0(9) . . . . ? C28 C2 C1 C6B 164.2(9) . . . . ? C28 C2 C1 C6A -166.9(7) . . . . ? C28 C2 C3A C14A -12.2(19) . . . . ? C28 C2 C3A C4A 169.6(11) . . . . ? C28 C2 C3B C4B -172.4(11) . . . . ? C28 C2 C3B C14B 18.9(15) . . . . ? C7 O1 C8 C9 3.1(8) . . . . ? C7 O1 C8 C13 -176.7(5) . . . . ? C7 C1 C6B C32B -7.2(16) . . . . ? C7 C1 C6B C5B 171.9(10) . . . . ? C7 C1 C6A C5A -168.3(10) . . . . ? C7 C1 C6A C32A 22.8(13) . . . . ? C13 C8 C9 C10 0.5(8) . . . . ? C1 C2 C28 C29 -90.8(7) . . . . ? C1 C2 C3A C14A -179.6(14) . . . . ? C1 C2 C3A C4A 2.1(18) . . . . ? C1 C2 C3B C4B -7.8(17) . . . . ? C1 C2 C3B C14B -176.5(9) . . . . ? C1 C6B C32B C33B 89.8(18) . . . . ? C1 C6B C5B C4B 0(2) . . . . ? C1 C6B C5B C21B -169.6(11) . . . . ? O2A C15A C20A C19A 179.7(14) . . . . ? O2A C15A C16A C17A 178.1(14) . . . . ? C6B C1 C6A C5A 117(2) . . . . ? C6B C1 C6A C32A -52.2(15) . . . . ? C16B C15B O2B C14B 168.5(11) . . . . ? C16B C17B C18B C19B 9(3) . . . . ? C16B C17B C18B Br2B -176.2(14) . . . . ? C3A C2 C28 C29 101.8(9) . . . . ? C3A C2 C1 C7 163.6(9) . . . . ? C3A C2 C1 C6B -29.2(14) . . . . ? C3A C2 C1 C6A -0.3(11) . . . . ? C3A C2 C3B C4B 103(4) . . . . ? C3A C2 C3B C14B -66(3) . . . . ? C3A C4A C5A C21A 178.9(13) . . . . ? C3A C4A C5A C6A -7(2) . . . . ? C25 C26 C27 C22 -0.5(9) . . . . ? C25 C24 C23 C22 0.1(10) . . . . ? C23 C22 O3 C21A -23.3(11) . . . . ? C23 C22 O3 C21B 174.5(10) . . . . ? C23 C24 C25 Br3 -177.8(5) . . . . ? C23 C24 C25 C26 0.6(10) . . . . ? C14A O2A C15A C20A -18.8(19) . . . . ? C14A O2A C15A C16A 167.8(13) . . . . ? C14A C3A C4A C30A 2(2) . . . . ? C14A C3A C4A C5A -176.7(16) . . . . ? C19B C20B C15B C16B 8(2) . . . . ? C19B C20B C15B O2B 178.8(15) . . . . ? C21A O3 C21B C5B 8.7(12) . . . . ? C21A C5A C6A C1 -176.6(10) . . . . ? C21A C5A C6A C32A -8.3(18) . . . . ? C18A C17A C16A C15A 3(2) . . . . ? C4B C3B C14B O2B -101.9(14) . . . . ? C32B C6B C5B C4B 179.1(13) . . . . ? C32B C6B C5B C21B 9.5(19) . . . . ? C30A C4A C5A C21A 0(2) . . . . ? C30A C4A C5A C6A 173.7(13) . . . . ? C31A C30A C4A C3A -101.0(18) . . . . ? C31A C30A C4A C5A 77.9(19) . . . . ? C30B C4B C5B C6B 179.6(13) . . . . ? C30B C4B C5B C21B -11(2) . . . . ? C30B C4B C3B C2 -175.3(12) . . . . ? C30B C4B C3B C14B -7(2) . . . . ? C4A C3A C14A O2A -89.3(18) . . . . ? C4A C5A C6A C1 10(2) . . . . ? C4A C5A C6A C32A 178.0(13) . . . . ? C21B O3 C21A C5A -12.3(13) . . . . ? C5B C6B C32B C33B -89.2(18) . . . . ? C5B C4B C30B C31B -103.8(17) . . . . ? C5B C4B C3B C2 11(2) . . . . ? C5B C4B C3B C14B 179.9(13) . . . . ? C33A C32A C6A C1 74.6(12) . . . . ? C33A C32A C6A C5A -94.6(15) . . . . ? C6A C1 C6B C32B 112(2) . . . . ? C6A C1 C6B C5B -68.6(17) . . . . ? C3B C2 C28 C29 72.8(10) . . . . ? C3B C2 C1 C7 -167.6(8) . . . . ? C3B C2 C1 C6B -0.4(13) . . . . ? C3B C2 C1 C6A 28.5(11) . . . . ? C3B C2 C3A C14A 97(4) . . . . ? C3B C2 C3A C4A -81(3) . . . . ? C3B C4B C30B C31B 83.3(19) . . . . ? C3B C4B C5B C6B -7(2) . . . . ? C3B C4B C5B C21B 162.1(12) . . . . ? C3B C14B O2B C15B -171.6(13) . . . . ? O2B C15B C16B C17B -177.7(14) . . . . ? C15A O2A C14A C3A -172.7(14) . . . . ? C15A C20A C19A C18A 2(3) . . . . ? C20A C15A C16A C17A 5(2) . . . . ? C19A C18A C17A C16A -9(3) . . . . ? C17A C18A C19A C20A 6(4) . . . . ? C16A C15A C20A C19A -7(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962416' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-gf-118K _audit_creation_date 2013-12-25 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-gf, 118 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 I3 O3' _chemical_formula_sum 'C33 H33 I3 O3' _chemical_formula_weight 858.29 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.4397(4) _cell_length_b 13.3256(3) _cell_length_c 26.3234(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.968(3) _cell_angle_gamma 90.00 _cell_volume 6448.7(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 8059 _cell_measurement_temperature 118(2) _cell_measurement_theta_max 29.0819 _cell_measurement_theta_min 3.7014 _exptl_absorpt_coefficient_mu 2.939 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.53371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 3312 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.07 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_unetI/netI 0.0523 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 35754 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.15 _diffrn_reflns_theta_min 3.71 _diffrn_ambient_temperature 118(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0348517000 _diffrn_orient_matrix_UB_12 0.0217131000 _diffrn_orient_matrix_UB_13 -0.0119558000 _diffrn_orient_matrix_UB_21 -0.0090686000 _diffrn_orient_matrix_UB_22 -0.0111751000 _diffrn_orient_matrix_UB_23 0.0234043000 _diffrn_orient_matrix_UB_31 0.0138412000 _diffrn_orient_matrix_UB_32 0.0472888000 _diffrn_orient_matrix_UB_33 0.0110048000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 11107 _reflns_number_total 15017 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.818 _refine_diff_density_min -1.154 _refine_diff_density_rms 0.126 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 15017 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0388 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+1.3804P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0767 _refine_ls_wR_factor_ref 0.0873 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C47(H47A,H47B), C54(H54A,H54B), C14(H14A,H14B), C21(H21A,H21B), C63(H63A,H63B), C28(H28A,H28B), C61(H61A,H61B), C40(H40A,H40B), C30(H30A,H30B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C26(H26), C49(H49), C52(H52), C19(H19), C57(H57), C23(H23), C20(H20), C59(H59), C13(H13), C50(H50), C17(H17), C60(H60), C42(H42), C27(H27), C46(H46), C16(H16), C9(H9), C12(H12), C43(H43), C10(H10), C24(H24), C53(H53), C56(H56), C45(H45) 2.c Idealised Me refined as rotating group: C62(H62A,H62B,H62C), C64(H64A,H64B,H64C), C33(H33A,H33B,H33C), C31(H31A,H31B, H31C), C66(H66A,H66B,H66C), C29(H29A,H29B,H29C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I5 I 0.542971(14) 0.69161(2) 0.286325(11) 0.02904(7) Uani 1 1 d . . . I2 I -0.034894(14) 0.30559(2) 0.727105(10) 0.02968(7) Uani 1 1 d . . . I6 I 0.327284(15) 0.45237(2) 0.775392(10) 0.03155(8) Uani 1 1 d . . . I3 I 0.170108(15) 0.56549(2) 0.211393(11) 0.03405(8) Uani 1 1 d . . . I4 I -0.019930(14) 1.54447(2) 0.410156(14) 0.03876(9) Uani 1 1 d . . . I1 I 0.529151(15) -0.52477(2) 0.594374(15) 0.04588(10) Uani 1 1 d . . . O2 O 0.17645(13) 0.18680(19) 0.60292(10) 0.0216(6) Uani 1 1 d . . . O3 O 0.23514(13) 0.2779(2) 0.40836(10) 0.0247(6) Uani 1 1 d . . . O1 O 0.40930(12) -0.08702(18) 0.56869(10) 0.0201(6) Uani 1 1 d . . . O6 O 0.23658(13) 0.71673(19) 0.56848(10) 0.0235(6) Uani 1 1 d . . . O5 O 0.31359(13) 0.82337(19) 0.39291(10) 0.0209(6) Uani 1 1 d . . . C7 C 0.34097(18) -0.0643(3) 0.52755(14) 0.0195(8) Uani 1 1 d . . . H7A H 0.3020 -0.1075 0.5321 0.023 Uiso 1 1 calc . . R H7B H 0.3450 -0.0774 0.4916 0.023 Uiso 1 1 calc . . R C26 C 0.1375(2) 0.4171(3) 0.28827(16) 0.0262(9) Uani 1 1 d . . . H26 H 0.0887 0.4254 0.2655 0.031 Uiso 1 1 calc . . R C8 C 0.43252(19) -0.1843(3) 0.57185(15) 0.0186(8) Uani 1 1 d . . . O4 O 0.05966(13) 1.08972(18) 0.41730(10) 0.0215(6) Uani 1 1 d . . . C3 C 0.28229(18) 0.1773(3) 0.57890(14) 0.0178(8) Uani 1 1 d . . . C36 C 0.20042(18) 0.8276(3) 0.40834(14) 0.0173(8) Uani 1 1 d . . . C48 C 0.36057(19) 0.7943(3) 0.36655(14) 0.0187(8) Uani 1 1 d . . . C25 C 0.1933(2) 0.4688(3) 0.27778(15) 0.0266(9) Uani 1 1 d . . . C51 C 0.4652(2) 0.7400(3) 0.32058(15) 0.0200(8) Uani 1 1 d . . . C47 C 0.23696(18) 0.8005(3) 0.36804(14) 0.0206(8) Uani 1 1 d . . . H47A H 0.2302 0.7283 0.3589 0.025 Uiso 1 1 calc . . R H47B H 0.2163 0.8401 0.3347 0.025 Uiso 1 1 calc . . R C54 C 0.16583(18) 0.7038(3) 0.52814(14) 0.0200(8) Uani 1 1 d . . . H54A H 0.1266 0.7175 0.5435 0.024 Uiso 1 1 calc . . R H54B H 0.1601 0.6345 0.5138 0.024 Uiso 1 1 calc . . R C49 C 0.3397(2) 0.7483(3) 0.31655(14) 0.0202(8) Uani 1 1 d . . . H49 H 0.2897 0.7356 0.2979 0.024 Uiso 1 1 calc . . R C35 C 0.17195(17) 0.9244(3) 0.40928(14) 0.0161(8) Uani 1 1 d . . . C2 C 0.30489(18) 0.0775(3) 0.57734(14) 0.0171(8) Uani 1 1 d . . . C37 C 0.19964(18) 0.7557(3) 0.44769(14) 0.0167(8) Uani 1 1 d . . . C5 C 0.30231(18) 0.2124(3) 0.49455(14) 0.0179(8) Uani 1 1 d . . . C18 C 0.0390(2) 0.2593(3) 0.68882(15) 0.0201(8) Uani 1 1 d . . . C4 C 0.27987(18) 0.2450(3) 0.53737(14) 0.0173(8) Uani 1 1 d . . . C41 C 0.04493(18) 1.1905(3) 0.41844(15) 0.0177(8) Uani 1 1 d . . . C55 C 0.25281(19) 0.6551(3) 0.61289(15) 0.0204(8) Uani 1 1 d . . . C14 C 0.25386(18) 0.2100(3) 0.62283(15) 0.0196(8) Uani 1 1 d . . . H14A H 0.2783 0.1729 0.6564 0.024 Uiso 1 1 calc . . R H14B H 0.2618 0.2828 0.6298 0.024 Uiso 1 1 calc . . R C52 C 0.4862(2) 0.7869(3) 0.37062(15) 0.0242(9) Uani 1 1 d . . . H52 H 0.5361 0.8005 0.3890 0.029 Uiso 1 1 calc . . R C15 C 0.13506(19) 0.2113(3) 0.63433(14) 0.0174(8) Uani 1 1 d . . . C19 C 0.01355(19) 0.2116(3) 0.63925(14) 0.0204(8) Uani 1 1 d . . . H19 H -0.0365 0.1952 0.6241 0.024 Uiso 1 1 calc . . R C21 C 0.3043(2) 0.2848(3) 0.45083(15) 0.0223(8) Uani 1 1 d . . . H21A H 0.3123 0.3541 0.4651 0.027 Uiso 1 1 calc . . R H21B H 0.3444 0.2671 0.4370 0.027 Uiso 1 1 calc . . R C57 C 0.3460(2) 0.6008(3) 0.69285(15) 0.0260(9) Uani 1 1 d . . . H57 H 0.3947 0.6039 0.7165 0.031 Uiso 1 1 calc . . R C23 C 0.2802(2) 0.3932(3) 0.35440(16) 0.0293(10) Uani 1 1 d . . . H23 H 0.3291 0.3852 0.3771 0.035 Uiso 1 1 calc . . R C11 C 0.4894(2) -0.3763(3) 0.58468(18) 0.0285(10) Uani 1 1 d . . . C63 C 0.23698(19) 0.6552(3) 0.44952(15) 0.0210(8) Uani 1 1 d . . . H63A H 0.2585 0.6342 0.4875 0.025 Uiso 1 1 calc . . R H63B H 0.2772 0.6633 0.4345 0.025 Uiso 1 1 calc . . R C20 C 0.06151(19) 0.1883(3) 0.61233(15) 0.0200(8) Uani 1 1 d . . . H20 H 0.0442 0.1561 0.5783 0.024 Uiso 1 1 calc . . R C39 C 0.13027(18) 0.8721(3) 0.48376(14) 0.0171(8) Uani 1 1 d . . . C22 C 0.2250(2) 0.3411(3) 0.36509(15) 0.0221(8) Uani 1 1 d . . . C59 C 0.2255(2) 0.5317(3) 0.66998(16) 0.0267(9) Uani 1 1 d . . . H59 H 0.1917 0.4880 0.6779 0.032 Uiso 1 1 calc . . R C13 C 0.4059(2) -0.2549(3) 0.53145(16) 0.0241(9) Uani 1 1 d . . . H13 H 0.3684 -0.2370 0.4993 0.029 Uiso 1 1 calc . . R C50 C 0.3921(2) 0.7208(3) 0.29395(15) 0.0213(8) Uani 1 1 d . . . H50 H 0.3780 0.6885 0.2599 0.026 Uiso 1 1 calc . . R C28 C 0.3436(2) 0.0782(3) 0.44321(15) 0.0218(8) Uani 1 1 d . . . H28A H 0.3227 0.1246 0.4127 0.026 Uiso 1 1 calc . . R H28B H 0.3239 0.0103 0.4319 0.026 Uiso 1 1 calc . . R C61 C 0.1718(2) 1.0013(3) 0.36764(15) 0.0223(8) Uani 1 1 d . . . H61A H 0.2164 0.9935 0.3576 0.027 Uiso 1 1 calc . . R H61B H 0.1727 1.0693 0.3831 0.027 Uiso 1 1 calc . . R C17 C 0.1123(2) 0.2813(3) 0.71131(15) 0.0216(8) Uani 1 1 d . . . H17 H 0.1296 0.3128 0.7455 0.026 Uiso 1 1 calc . . R C60 C 0.20389(19) 0.5904(3) 0.62395(15) 0.0236(9) Uani 1 1 d . . . H60 H 0.1554 0.5862 0.6000 0.028 Uiso 1 1 calc . . R C44 C 0.00679(19) 1.3909(3) 0.41351(16) 0.0229(9) Uani 1 1 d . . . C1 C 0.32286(18) 0.0443(3) 0.53221(15) 0.0179(8) Uani 1 1 d . . . C42 C 0.07833(19) 1.2530(3) 0.46166(16) 0.0217(8) Uani 1 1 d . . . H42 H 0.1141 1.2271 0.4928 0.026 Uiso 1 1 calc . . R C27 C 0.1532(2) 0.3532(3) 0.33217(15) 0.0228(9) Uani 1 1 d . . . H27 H 0.1152 0.3178 0.3397 0.027 Uiso 1 1 calc . . R C46 C -0.00716(19) 1.2282(3) 0.37276(15) 0.0219(8) Uani 1 1 d . . . H46 H -0.0297 1.1852 0.3433 0.026 Uiso 1 1 calc . . R C16 C 0.16068(19) 0.2576(3) 0.68434(14) 0.0198(8) Uani 1 1 d . . . H16 H 0.2109 0.2728 0.6999 0.024 Uiso 1 1 calc . . R C58 C 0.2961(2) 0.5372(3) 0.70410(15) 0.0233(9) Uani 1 1 d . . . C38 C 0.16327(18) 0.7787(3) 0.48423(14) 0.0173(8) Uani 1 1 d . . . C40 C 0.12334(19) 1.0550(3) 0.45880(15) 0.0208(8) Uani 1 1 d . . . H40A H 0.1156 1.0605 0.4940 0.025 Uiso 1 1 calc . . R H40B H 0.1653 1.0980 0.4597 0.025 Uiso 1 1 calc . . R C30 C 0.3101(2) 0.0067(3) 0.62348(15) 0.0224(8) Uani 1 1 d . . . H30A H 0.3057 -0.0632 0.6102 0.027 Uiso 1 1 calc . . R H30B H 0.2691 0.0198 0.6370 0.027 Uiso 1 1 calc . . R C34 C 0.14011(18) 0.9473(3) 0.44926(14) 0.0159(7) Uani 1 1 d . . . C9 C 0.4878(2) -0.2109(3) 0.61845(16) 0.0253(9) Uani 1 1 d . . . H9 H 0.5065 -0.1626 0.6461 0.030 Uiso 1 1 calc . . R C32 C 0.25381(19) 0.3521(3) 0.53833(16) 0.0227(9) Uani 1 1 d . . . H32A H 0.2176 0.3537 0.5575 0.027 Uiso 1 1 calc . . R H32B H 0.2292 0.3747 0.5010 0.027 Uiso 1 1 calc . . R C62 C 0.1049(2) 0.9917(3) 0.31708(16) 0.0323(10) Uani 1 1 d . . . H62A H 0.0608 1.0045 0.3263 0.048 Uiso 1 1 calc . . GR H62B H 0.1030 0.9238 0.3024 0.048 Uiso 1 1 calc . . GR H62C H 0.1083 1.0407 0.2902 0.048 Uiso 1 1 calc . . GR C12 C 0.4340(2) -0.3514(3) 0.53790(17) 0.0290(10) Uani 1 1 d . . . H12 H 0.4155 -0.4000 0.5105 0.035 Uiso 1 1 calc . . R C6 C 0.32187(17) 0.1116(3) 0.49077(15) 0.0179(8) Uani 1 1 d . . . C43 C 0.0590(2) 1.3535(3) 0.45890(16) 0.0248(9) Uani 1 1 d . . . H43 H 0.0816 1.3969 0.4882 0.030 Uiso 1 1 calc . . R C10 C 0.5157(2) -0.3071(3) 0.62478(16) 0.0261(9) Uani 1 1 d . . . H10 H 0.5532 -0.3252 0.6569 0.031 Uiso 1 1 calc . . R C24 C 0.2645(2) 0.4571(3) 0.31076(17) 0.0309(10) Uani 1 1 d . . . H24 H 0.3024 0.4929 0.3034 0.037 Uiso 1 1 calc . . R C64 C 0.1865(2) 0.5723(3) 0.41862(17) 0.0311(10) Uani 1 1 d . . . H64A H 0.1458 0.5646 0.4326 0.047 Uiso 1 1 calc . . GR H64B H 0.2135 0.5091 0.4229 0.047 Uiso 1 1 calc . . GR H64C H 0.1676 0.5900 0.3804 0.047 Uiso 1 1 calc . . GR C33 C 0.3153(2) 0.4249(3) 0.56556(17) 0.0308(10) Uani 1 1 d . . . H33A H 0.3525 0.4214 0.5479 0.046 Uiso 1 1 calc . . GR H33B H 0.3370 0.4068 0.6035 0.046 Uiso 1 1 calc . . GR H33C H 0.2960 0.4934 0.5628 0.046 Uiso 1 1 calc . . GR C53 C 0.4341(2) 0.8136(3) 0.39340(15) 0.0226(8) Uani 1 1 d . . . H53 H 0.4484 0.8453 0.4276 0.027 Uiso 1 1 calc . . R C56 C 0.3246(2) 0.6598(3) 0.64705(15) 0.0241(9) Uani 1 1 d . . . H56 H 0.3585 0.7030 0.6390 0.029 Uiso 1 1 calc . . R C65 C 0.08381(19) 0.8925(3) 0.51931(14) 0.0204(8) Uani 1 1 d . . . H65A H 0.0560 0.8309 0.5207 0.024 Uiso 1 1 calc . . R H65B H 0.0482 0.9456 0.5022 0.024 Uiso 1 1 calc . . R C45 C -0.0260(2) 1.3287(3) 0.37041(16) 0.0250(9) Uani 1 1 d . . . H45 H -0.0615 1.3549 0.3392 0.030 Uiso 1 1 calc . . R C31 C 0.3819(2) 0.0181(3) 0.66995(16) 0.0312(10) Uani 1 1 d . . . H31A H 0.4228 0.0048 0.6569 0.047 Uiso 1 1 calc . . GR H31B H 0.3830 -0.0298 0.6984 0.047 Uiso 1 1 calc . . GR H31C H 0.3857 0.0865 0.6842 0.047 Uiso 1 1 calc . . GR C66 C 0.1251(2) 0.9245(3) 0.57667(15) 0.0278(9) Uani 1 1 d . . . H66A H 0.1587 0.8710 0.5949 0.042 Uiso 1 1 calc . . GR H66B H 0.0906 0.9373 0.5960 0.042 Uiso 1 1 calc . . GR H66C H 0.1527 0.9859 0.5761 0.042 Uiso 1 1 calc . . GR C29 C 0.4260(2) 0.0764(4) 0.45755(17) 0.0355(11) Uani 1 1 d . . . H29A H 0.4390 0.0487 0.4274 0.053 Uiso 1 1 calc . . GR H29B H 0.4470 0.0345 0.4894 0.053 Uiso 1 1 calc . . GR H29C H 0.4450 0.1449 0.4650 0.053 Uiso 1 1 calc . . GR 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 I5 0.02601(13) 0.03764(17) 0.02831(14) -0.00560(13) 0.01549(12) 0.00218(12) I2 0.02907(14) 0.03989(17) 0.02452(14) -0.00481(13) 0.01482(11) 0.00303(12) I6 0.03683(15) 0.03822(17) 0.01896(13) 0.00904(13) 0.00817(12) 0.01034(13) I3 0.03965(16) 0.04217(18) 0.02212(14) 0.01030(13) 0.01252(12) 0.01390(13) I4 0.02704(14) 0.01637(14) 0.0672(2) 0.00970(15) 0.00750(14) 0.00427(11) I1 0.03071(15) 0.01940(15) 0.0805(3) 0.01354(16) 0.00836(16) 0.00732(12) O2 0.0177(12) 0.0272(15) 0.0208(13) -0.0071(12) 0.0074(11) -0.0018(11) O3 0.0212(13) 0.0280(16) 0.0230(14) 0.0106(13) 0.0048(12) -0.0008(11) O1 0.0185(12) 0.0135(13) 0.0247(14) -0.0033(12) 0.0019(11) 0.0005(10) O6 0.0228(13) 0.0237(15) 0.0195(13) 0.0092(12) 0.0006(11) -0.0032(11) O5 0.0185(12) 0.0265(15) 0.0196(13) -0.0050(12) 0.0087(11) -0.0007(11) C7 0.0179(17) 0.018(2) 0.0183(18) 0.0035(17) -0.0001(15) 0.0017(15) C26 0.0240(19) 0.027(2) 0.024(2) -0.0018(19) 0.0032(17) 0.0042(17) C8 0.0181(17) 0.018(2) 0.0220(19) 0.0024(17) 0.0093(16) 0.0011(15) O4 0.0198(12) 0.0157(14) 0.0252(14) -0.0007(12) 0.0020(11) 0.0035(11) C3 0.0134(16) 0.021(2) 0.0186(18) -0.0008(17) 0.0050(15) 0.0010(14) C36 0.0143(16) 0.021(2) 0.0149(17) 0.0007(16) 0.0027(14) -0.0001(15) C48 0.0227(18) 0.019(2) 0.0175(18) 0.0026(16) 0.0109(16) 0.0029(15) C25 0.035(2) 0.024(2) 0.022(2) 0.0019(18) 0.0113(18) 0.0051(18) C51 0.0249(18) 0.019(2) 0.0209(19) 0.0022(17) 0.0136(16) 0.0050(16) C47 0.0159(16) 0.027(2) 0.0189(18) -0.0016(18) 0.0056(15) 0.0029(15) C54 0.0183(17) 0.019(2) 0.0214(19) 0.0020(17) 0.0054(16) -0.0031(15) C49 0.0225(18) 0.018(2) 0.0193(19) 0.0009(17) 0.0060(16) 0.0040(15) C35 0.0138(16) 0.0136(18) 0.0194(18) 0.0012(16) 0.0033(15) -0.0027(14) C2 0.0128(16) 0.0180(19) 0.0210(19) 0.0034(16) 0.0063(15) 0.0005(14) C37 0.0177(17) 0.0154(19) 0.0162(18) -0.0010(16) 0.0043(15) -0.0002(14) C5 0.0145(16) 0.0178(19) 0.0200(19) 0.0036(17) 0.0035(15) -0.0001(15) C18 0.0247(18) 0.020(2) 0.0202(19) 0.0010(17) 0.0135(16) 0.0032(16) C4 0.0147(16) 0.0155(19) 0.0200(19) 0.0000(16) 0.0033(15) 0.0002(14) C41 0.0184(17) 0.0131(18) 0.0242(19) 0.0032(17) 0.0104(16) 0.0025(14) C55 0.0233(18) 0.018(2) 0.0198(19) 0.0013(17) 0.0063(16) 0.0029(15) C14 0.0137(16) 0.022(2) 0.0223(19) -0.0058(17) 0.0053(15) -0.0011(15) C52 0.0219(18) 0.026(2) 0.025(2) -0.0027(18) 0.0074(17) -0.0009(16) C15 0.0208(17) 0.0146(19) 0.0191(18) 0.0023(16) 0.0098(15) 0.0041(15) C19 0.0194(17) 0.021(2) 0.0203(19) -0.0021(17) 0.0053(16) -0.0023(15) C21 0.0223(18) 0.019(2) 0.024(2) 0.0034(18) 0.0055(16) 0.0016(16) C57 0.0245(19) 0.030(2) 0.019(2) -0.0042(19) 0.0024(17) 0.0000(17) C23 0.0202(18) 0.036(2) 0.033(2) 0.015(2) 0.0102(18) 0.0060(18) C11 0.0228(19) 0.017(2) 0.046(3) 0.014(2) 0.0106(19) 0.0046(16) C63 0.0222(18) 0.0154(19) 0.022(2) -0.0033(17) 0.0032(16) 0.0038(15) C20 0.0212(18) 0.022(2) 0.0171(18) -0.0077(17) 0.0060(16) -0.0035(15) C39 0.0141(16) 0.019(2) 0.0165(18) 0.0004(16) 0.0019(15) 0.0011(14) C22 0.0266(19) 0.018(2) 0.022(2) 0.0013(17) 0.0079(17) 0.0042(16) C59 0.0220(19) 0.031(2) 0.029(2) 0.0076(19) 0.0101(18) 0.0004(17) C13 0.0221(19) 0.022(2) 0.025(2) 0.0001(18) 0.0032(17) 0.0004(16) C50 0.0261(19) 0.021(2) 0.0166(18) -0.0028(17) 0.0060(16) 0.0027(16) C28 0.0251(19) 0.018(2) 0.023(2) 0.0036(17) 0.0090(17) 0.0032(16) C61 0.0245(19) 0.021(2) 0.024(2) 0.0074(18) 0.0111(17) 0.0025(16) C17 0.0278(19) 0.022(2) 0.0148(18) -0.0002(17) 0.0061(16) 0.0030(16) C60 0.0181(17) 0.025(2) 0.025(2) 0.0086(18) 0.0039(16) -0.0007(16) C44 0.0205(18) 0.0123(19) 0.038(2) 0.0056(18) 0.0118(18) 0.0035(15) C1 0.0155(16) 0.0150(19) 0.0229(19) 0.0015(16) 0.0060(15) 0.0009(14) C42 0.0198(18) 0.017(2) 0.026(2) 0.0030(18) 0.0036(16) 0.0033(15) C27 0.0208(18) 0.022(2) 0.025(2) -0.0041(18) 0.0061(17) -0.0024(16) C46 0.0203(18) 0.024(2) 0.022(2) 0.0018(18) 0.0073(16) 0.0002(16) C16 0.0184(17) 0.020(2) 0.0195(19) 0.0001(17) 0.0037(16) 0.0011(15) C58 0.029(2) 0.024(2) 0.0172(19) 0.0042(17) 0.0083(17) 0.0083(17) C38 0.0174(17) 0.0170(19) 0.0160(18) -0.0002(16) 0.0034(15) -0.0048(15) C40 0.0193(17) 0.019(2) 0.023(2) -0.0003(17) 0.0051(16) 0.0031(15) C30 0.0264(19) 0.020(2) 0.0210(19) 0.0009(17) 0.0087(17) 0.0004(16) C34 0.0156(16) 0.0120(18) 0.0172(18) 0.0013(16) 0.0012(15) -0.0004(14) C9 0.0244(19) 0.026(2) 0.024(2) -0.0011(19) 0.0059(17) -0.0001(17) C32 0.0200(18) 0.019(2) 0.029(2) 0.0012(18) 0.0071(17) 0.0037(15) C62 0.035(2) 0.032(2) 0.031(2) 0.012(2) 0.0107(19) 0.0038(19) C12 0.027(2) 0.019(2) 0.035(2) 0.000(2) 0.0006(19) 0.0005(17) C6 0.0105(15) 0.020(2) 0.0231(19) 0.0022(17) 0.0047(15) 0.0025(14) C43 0.0224(18) 0.019(2) 0.029(2) -0.0021(19) 0.0035(17) -0.0006(16) C10 0.0223(19) 0.024(2) 0.028(2) 0.010(2) 0.0024(17) 0.0034(17) C24 0.0234(19) 0.040(3) 0.033(2) 0.012(2) 0.0145(18) 0.0051(18) C64 0.035(2) 0.021(2) 0.035(2) -0.006(2) 0.008(2) 0.0050(18) C33 0.035(2) 0.020(2) 0.034(2) -0.006(2) 0.007(2) -0.0027(18) C53 0.0251(19) 0.022(2) 0.0212(19) -0.0035(18) 0.0087(17) -0.0017(16) C56 0.0242(19) 0.023(2) 0.025(2) -0.0013(18) 0.0080(17) -0.0043(16) C65 0.0175(17) 0.019(2) 0.025(2) 0.0008(17) 0.0068(16) 0.0015(15) C45 0.0194(18) 0.027(2) 0.029(2) 0.0116(19) 0.0078(17) 0.0062(16) C31 0.033(2) 0.034(3) 0.025(2) 0.008(2) 0.0059(19) 0.0034(19) C66 0.030(2) 0.031(2) 0.025(2) -0.0064(19) 0.0118(18) -0.0055(18) C29 0.030(2) 0.045(3) 0.037(2) 0.000(2) 0.019(2) 0.006(2) _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 I5 C51 2.099(4) . ? I2 C18 2.098(4) . ? I6 C58 2.104(4) . ? I3 C25 2.099(4) . ? I4 C44 2.106(4) . ? I1 C11 2.109(4) . ? O2 C14 1.457(4) . ? O2 C15 1.367(4) . ? O3 C21 1.446(4) . ? O3 C22 1.378(4) . ? O1 C7 1.447(4) . ? O1 C8 1.366(4) . ? O6 C54 1.449(4) . ? O6 C55 1.379(4) . ? O5 C48 1.370(4) . ? O5 C47 1.451(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C1 1.503(5) . ? C26 H26 0.9500 . ? C26 C25 1.387(6) . ? C26 C27 1.387(5) . ? C8 C13 1.387(5) . ? C8 C9 1.389(5) . ? O4 C41 1.376(4) . ? O4 C40 1.435(4) . ? C3 C2 1.405(5) . ? C3 C4 1.406(5) . ? C3 C14 1.499(5) . ? C36 C47 1.500(5) . ? C36 C35 1.407(5) . ? C36 C37 1.415(5) . ? C48 C49 1.388(5) . ? C48 C53 1.397(5) . ? C25 C24 1.382(5) . ? C51 C52 1.394(5) . ? C51 C50 1.388(5) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C54 C38 1.515(5) . ? C49 H49 0.9500 . ? C49 C50 1.386(5) . ? C35 C61 1.500(5) . ? C35 C34 1.417(5) . ? C2 C1 1.414(5) . ? C2 C30 1.515(5) . ? C37 C63 1.517(5) . ? C37 C38 1.401(5) . ? C5 C4 1.403(5) . ? C5 C21 1.512(5) . ? C5 C6 1.408(5) . ? C18 C19 1.390(5) . ? C18 C17 1.384(5) . ? C4 C32 1.518(5) . ? C41 C42 1.389(5) . ? C41 C46 1.390(5) . ? C55 C60 1.383(5) . ? C55 C56 1.394(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C52 H52 0.9500 . ? C52 C53 1.380(5) . ? C15 C20 1.391(5) . ? C15 C16 1.391(5) . ? C19 H19 0.9500 . ? C19 C20 1.377(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C57 H57 0.9500 . ? C57 C58 1.391(5) . ? C57 C56 1.385(5) . ? C23 H23 0.9500 . ? C23 C22 1.382(5) . ? C23 C24 1.381(5) . ? C11 C12 1.387(5) . ? C11 C10 1.370(6) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C63 C64 1.525(5) . ? C20 H20 0.9500 . ? C39 C38 1.398(5) . ? C39 C34 1.407(5) . ? C39 C65 1.521(5) . ? C22 C27 1.392(5) . ? C59 H59 0.9500 . ? C59 C60 1.388(5) . ? C59 C58 1.377(5) . ? C13 H13 0.9500 . ? C13 C12 1.386(5) . ? C50 H50 0.9500 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C6 1.513(5) . ? C28 C29 1.521(5) . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C61 C62 1.534(5) . ? C17 H17 0.9500 . ? C17 C16 1.386(5) . ? C60 H60 0.9500 . ? C44 C43 1.384(5) . ? C44 C45 1.382(6) . ? C1 C6 1.408(5) . ? C42 H42 0.9500 . ? C42 C43 1.387(5) . ? C27 H27 0.9500 . ? C46 H46 0.9500 . ? C46 C45 1.384(5) . ? C16 H16 0.9500 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C40 C34 1.511(5) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 C31 1.535(5) . ? C9 H9 0.9500 . ? C9 C10 1.381(5) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C33 1.526(5) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C12 H12 0.9500 . ? C43 H43 0.9500 . ? C10 H10 0.9500 . ? C24 H24 0.9500 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C53 H53 0.9500 . ? C56 H56 0.9500 . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C65 C66 1.523(5) . ? C45 H45 0.9500 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O2 C14 118.3(3) . . ? C22 O3 C21 116.5(3) . . ? C8 O1 C7 116.7(3) . . ? C55 O6 C54 116.9(3) . . ? C48 O5 C47 117.9(3) . . ? O1 C7 H7A 109.9 . . ? O1 C7 H7B 109.9 . . ? O1 C7 C1 108.8(3) . . ? H7A C7 H7B 108.3 . . ? C1 C7 H7A 109.9 . . ? C1 C7 H7B 109.9 . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C27 C26 C25 119.7(3) . . ? O1 C8 C13 124.2(3) . . ? O1 C8 C9 116.2(3) . . ? C13 C8 C9 119.6(3) . . ? C41 O4 C40 115.6(3) . . ? C2 C3 C4 121.1(3) . . ? C2 C3 C14 119.7(3) . . ? C4 C3 C14 119.0(3) . . ? C35 C36 C47 120.8(3) . . ? C35 C36 C37 120.7(3) . . ? C37 C36 C47 118.4(3) . . ? O5 C48 C49 124.5(3) . . ? O5 C48 C53 115.7(3) . . ? C49 C48 C53 119.8(3) . . ? C26 C25 I3 120.0(3) . . ? C24 C25 I3 119.5(3) . . ? C24 C25 C26 120.5(4) . . ? C52 C51 I5 120.9(3) . . ? C50 C51 I5 119.2(3) . . ? C50 C51 C52 119.8(4) . . ? O5 C47 C36 106.4(3) . . ? O5 C47 H47A 110.4 . . ? O5 C47 H47B 110.4 . . ? C36 C47 H47A 110.4 . . ? C36 C47 H47B 110.4 . . ? H47A C47 H47B 108.6 . . ? O6 C54 H54A 110.6 . . ? O6 C54 H54B 110.6 . . ? O6 C54 C38 105.6(3) . . ? H54A C54 H54B 108.8 . . ? C38 C54 H54A 110.6 . . ? C38 C54 H54B 110.6 . . ? C48 C49 H49 120.2 . . ? C50 C49 C48 119.6(3) . . ? C50 C49 H49 120.2 . . ? C36 C35 C61 121.4(3) . . ? C36 C35 C34 118.7(3) . . ? C34 C35 C61 119.9(3) . . ? C3 C2 C1 119.1(3) . . ? C3 C2 C30 120.4(3) . . ? C1 C2 C30 120.5(3) . . ? C36 C37 C63 120.2(3) . . ? C38 C37 C36 118.8(3) . . ? C38 C37 C63 121.0(3) . . ? C4 C5 C21 120.4(3) . . ? C4 C5 C6 120.9(3) . . ? C6 C5 C21 118.7(3) . . ? C19 C18 I2 119.6(3) . . ? C17 C18 I2 120.2(3) . . ? C17 C18 C19 120.1(3) . . ? C3 C4 C32 121.2(3) . . ? C5 C4 C3 119.0(3) . . ? C5 C4 C32 119.8(3) . . ? O4 C41 C42 123.9(3) . . ? O4 C41 C46 115.6(3) . . ? C42 C41 C46 120.5(3) . . ? O6 C55 C60 124.5(3) . . ? O6 C55 C56 115.2(3) . . ? C60 C55 C56 120.3(3) . . ? O2 C14 C3 104.9(3) . . ? O2 C14 H14A 110.8 . . ? O2 C14 H14B 110.8 . . ? C3 C14 H14A 110.8 . . ? C3 C14 H14B 110.8 . . ? H14A C14 H14B 108.8 . . ? C51 C52 H52 120.2 . . ? C53 C52 C51 119.7(3) . . ? C53 C52 H52 120.2 . . ? O2 C15 C20 115.0(3) . . ? O2 C15 C16 125.3(3) . . ? C16 C15 C20 119.7(3) . . ? C18 C19 H19 120.3 . . ? C20 C19 C18 119.4(3) . . ? C20 C19 H19 120.3 . . ? O3 C21 C5 107.5(3) . . ? O3 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C5 C21 H21A 110.2 . . ? C5 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C58 C57 H57 120.1 . . ? C56 C57 H57 120.1 . . ? C56 C57 C58 119.8(3) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C24 C23 C22 120.1(4) . . ? C12 C11 I1 118.7(3) . . ? C10 C11 I1 120.5(3) . . ? C10 C11 C12 120.7(4) . . ? C37 C63 H63A 108.8 . . ? C37 C63 H63B 108.8 . . ? C37 C63 C64 113.8(3) . . ? H63A C63 H63B 107.7 . . ? C64 C63 H63A 108.8 . . ? C64 C63 H63B 108.8 . . ? C15 C20 H20 119.6 . . ? C19 C20 C15 120.8(3) . . ? C19 C20 H20 119.6 . . ? C38 C39 C34 118.8(3) . . ? C38 C39 C65 121.1(3) . . ? C34 C39 C65 120.1(3) . . ? O3 C22 C23 124.3(3) . . ? O3 C22 C27 115.5(3) . . ? C23 C22 C27 120.2(4) . . ? C60 C59 H59 120.2 . . ? C58 C59 H59 120.2 . . ? C58 C59 C60 119.6(4) . . ? C8 C13 H13 120.0 . . ? C12 C13 C8 120.1(3) . . ? C12 C13 H13 120.0 . . ? C51 C50 H50 119.7 . . ? C49 C50 C51 120.6(3) . . ? C49 C50 H50 119.7 . . ? H28A C28 H28B 108.1 . . ? C6 C28 H28A 109.5 . . ? C6 C28 H28B 109.5 . . ? C6 C28 C29 110.7(3) . . ? C29 C28 H28A 109.5 . . ? C29 C28 H28B 109.5 . . ? C35 C61 H61A 109.2 . . ? C35 C61 H61B 109.2 . . ? C35 C61 C62 112.1(3) . . ? H61A C61 H61B 107.9 . . ? C62 C61 H61A 109.2 . . ? C62 C61 H61B 109.2 . . ? C18 C17 H17 119.7 . . ? C18 C17 C16 120.5(3) . . ? C16 C17 H17 119.7 . . ? C55 C60 C59 120.1(3) . . ? C55 C60 H60 119.9 . . ? C59 C60 H60 119.9 . . ? C43 C44 I4 119.2(3) . . ? C45 C44 I4 120.4(3) . . ? C45 C44 C43 120.4(3) . . ? C2 C1 C7 119.9(3) . . ? C6 C1 C7 119.7(3) . . ? C6 C1 C2 120.4(3) . . ? C41 C42 H42 120.3 . . ? C43 C42 C41 119.3(3) . . ? C43 C42 H42 120.3 . . ? C26 C27 C22 119.7(4) . . ? C26 C27 H27 120.2 . . ? C22 C27 H27 120.2 . . ? C41 C46 H46 120.1 . . ? C45 C46 C41 119.7(4) . . ? C45 C46 H46 120.1 . . ? C15 C16 H16 120.3 . . ? C17 C16 C15 119.5(3) . . ? C17 C16 H16 120.3 . . ? C57 C58 I6 119.9(3) . . ? C59 C58 I6 119.4(3) . . ? C59 C58 C57 120.7(4) . . ? C37 C38 C54 118.7(3) . . ? C39 C38 C54 119.6(3) . . ? C39 C38 C37 121.4(3) . . ? O4 C40 H40A 109.4 . . ? O4 C40 H40B 109.4 . . ? O4 C40 C34 111.0(3) . . ? H40A C40 H40B 108.0 . . ? C34 C40 H40A 109.4 . . ? C34 C40 H40B 109.4 . . ? C2 C30 H30A 109.1 . . ? C2 C30 H30B 109.1 . . ? C2 C30 C31 112.6(3) . . ? H30A C30 H30B 107.8 . . ? C31 C30 H30A 109.1 . . ? C31 C30 H30B 109.1 . . ? C35 C34 C40 119.9(3) . . ? C39 C34 C35 120.7(3) . . ? C39 C34 C40 119.2(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 C8 120.3(4) . . ? C10 C9 H9 119.9 . . ? C4 C32 H32A 109.0 . . ? C4 C32 H32B 109.0 . . ? C4 C32 C33 113.0(3) . . ? H32A C32 H32B 107.8 . . ? C33 C32 H32A 109.0 . . ? C33 C32 H32B 109.0 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C11 C12 H12 120.2 . . ? C13 C12 C11 119.5(4) . . ? C13 C12 H12 120.2 . . ? C5 C6 C28 119.6(3) . . ? C1 C6 C5 119.3(3) . . ? C1 C6 C28 121.1(3) . . ? C44 C43 C42 120.2(4) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C11 C10 C9 119.9(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C25 C24 H24 120.1 . . ? C23 C24 C25 119.9(4) . . ? C23 C24 H24 120.1 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C48 C53 H53 119.8 . . ? C52 C53 C48 120.5(4) . . ? C52 C53 H53 119.8 . . ? C55 C56 H56 120.3 . . ? C57 C56 C55 119.5(4) . . ? C57 C56 H56 120.3 . . ? C39 C65 H65A 108.4 . . ? C39 C65 H65B 108.4 . . ? C39 C65 C66 115.7(3) . . ? H65A C65 H65B 107.4 . . ? C66 C65 H65A 108.4 . . ? C66 C65 H65B 108.4 . . ? C44 C45 C46 119.9(3) . . ? C44 C45 H45 120.1 . . ? C46 C45 H45 120.1 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I5 C51 C52 C53 -176.8(3) . . . . ? I5 C51 C50 C49 177.4(3) . . . . ? I2 C18 C19 C20 175.0(3) . . . . ? I2 C18 C17 C16 -175.2(3) . . . . ? I3 C25 C24 C23 -179.7(3) . . . . ? I4 C44 C43 C42 -178.9(3) . . . . ? I4 C44 C45 C46 179.0(3) . . . . ? I1 C11 C12 C13 178.3(3) . . . . ? I1 C11 C10 C9 -178.3(3) . . . . ? O2 C15 C20 C19 -178.2(3) . . . . ? O2 C15 C16 C17 177.9(3) . . . . ? O3 C22 C27 C26 178.6(3) . . . . ? O1 C7 C1 C2 -68.0(4) . . . . ? O1 C7 C1 C6 113.8(3) . . . . ? O1 C8 C13 C12 178.6(4) . . . . ? O1 C8 C9 C10 -178.8(4) . . . . ? O6 C54 C38 C37 78.3(4) . . . . ? O6 C54 C38 C39 -96.3(4) . . . . ? O6 C55 C60 C59 -179.7(4) . . . . ? O6 C55 C56 C57 179.8(3) . . . . ? O5 C48 C49 C50 -179.1(3) . . . . ? O5 C48 C53 C52 179.7(3) . . . . ? C7 O1 C8 C13 16.7(5) . . . . ? C7 O1 C8 C9 -165.2(3) . . . . ? C7 C1 C6 C5 177.7(3) . . . . ? C7 C1 C6 C28 -4.1(5) . . . . ? C26 C25 C24 C23 0.2(6) . . . . ? C8 O1 C7 C1 177.1(3) . . . . ? C8 C13 C12 C11 -0.7(6) . . . . ? C8 C9 C10 C11 0.8(6) . . . . ? O4 C41 C42 C43 -179.4(4) . . . . ? O4 C41 C46 C45 179.5(3) . . . . ? O4 C40 C34 C35 75.9(4) . . . . ? O4 C40 C34 C39 -110.2(4) . . . . ? C3 C2 C1 C7 -174.8(3) . . . . ? C3 C2 C1 C6 3.4(5) . . . . ? C3 C2 C30 C31 -82.8(4) . . . . ? C3 C4 C32 C33 91.3(4) . . . . ? C36 C35 C61 C62 85.6(4) . . . . ? C36 C35 C34 C39 -6.5(5) . . . . ? C36 C35 C34 C40 167.3(3) . . . . ? C36 C37 C63 C64 -94.0(4) . . . . ? C36 C37 C38 C54 -176.8(3) . . . . ? C36 C37 C38 C39 -2.3(5) . . . . ? C48 O5 C47 C36 172.5(3) . . . . ? C48 C49 C50 C51 -0.8(6) . . . . ? C25 C26 C27 C22 -0.4(6) . . . . ? C51 C52 C53 C48 -0.3(6) . . . . ? C47 O5 C48 C49 2.9(5) . . . . ? C47 O5 C48 C53 -176.9(3) . . . . ? C47 C36 C35 C61 4.8(5) . . . . ? C47 C36 C35 C34 -177.9(3) . . . . ? C47 C36 C37 C63 1.7(5) . . . . ? C47 C36 C37 C38 -177.6(3) . . . . ? C54 O6 C55 C60 -7.2(5) . . . . ? C54 O6 C55 C56 171.5(3) . . . . ? C49 C48 C53 C52 -0.2(6) . . . . ? C35 C36 C47 O5 90.5(4) . . . . ? C35 C36 C37 C63 -174.0(3) . . . . ? C35 C36 C37 C38 6.6(5) . . . . ? C2 C3 C4 C5 -1.7(5) . . . . ? C2 C3 C4 C32 178.6(3) . . . . ? C2 C3 C14 O2 -87.1(4) . . . . ? C2 C1 C6 C5 -0.4(5) . . . . ? C2 C1 C6 C28 177.7(3) . . . . ? C37 C36 C47 O5 -85.3(4) . . . . ? C37 C36 C35 C61 -179.5(3) . . . . ? C37 C36 C35 C34 -2.2(5) . . . . ? C5 C4 C32 C33 -88.5(4) . . . . ? C18 C19 C20 C15 0.4(6) . . . . ? C18 C17 C16 C15 0.0(6) . . . . ? C4 C3 C2 C1 -2.3(5) . . . . ? C4 C3 C2 C30 177.5(3) . . . . ? C4 C3 C14 O2 87.4(4) . . . . ? C4 C5 C21 O3 -92.5(4) . . . . ? C4 C5 C6 C28 178.1(3) . . . . ? C4 C5 C6 C1 -3.7(5) . . . . ? C41 O4 C40 C34 -172.1(3) . . . . ? C41 C42 C43 C44 0.1(6) . . . . ? C41 C46 C45 C44 -0.2(6) . . . . ? C55 O6 C54 C38 -179.1(3) . . . . ? C14 O2 C15 C20 179.1(3) . . . . ? C14 O2 C15 C16 0.3(5) . . . . ? C14 C3 C2 C1 172.1(3) . . . . ? C14 C3 C2 C30 -8.1(5) . . . . ? C14 C3 C4 C5 -176.1(3) . . . . ? C14 C3 C4 C32 4.1(5) . . . . ? C52 C51 C50 C49 0.3(6) . . . . ? C15 O2 C14 C3 -178.2(3) . . . . ? C19 C18 C17 C16 1.1(6) . . . . ? C21 O3 C22 C23 14.4(5) . . . . ? C21 O3 C22 C27 -163.4(3) . . . . ? C21 C5 C4 C3 -176.6(3) . . . . ? C21 C5 C4 C32 3.1(5) . . . . ? C21 C5 C6 C28 -0.5(5) . . . . ? C21 C5 C6 C1 177.6(3) . . . . ? C23 C22 C27 C26 0.7(6) . . . . ? C63 C37 C38 C54 3.8(5) . . . . ? C63 C37 C38 C39 178.4(3) . . . . ? C20 C15 C16 C17 -0.8(5) . . . . ? C22 O3 C21 C5 177.9(3) . . . . ? C22 C23 C24 C25 0.0(7) . . . . ? C13 C8 C9 C10 -0.6(6) . . . . ? C50 C51 C52 C53 0.2(6) . . . . ? C61 C35 C34 C39 170.8(3) . . . . ? C61 C35 C34 C40 -15.4(5) . . . . ? C17 C18 C19 C20 -1.3(6) . . . . ? C60 C55 C56 C57 -1.5(6) . . . . ? C60 C59 C58 I6 177.5(3) . . . . ? C60 C59 C58 C57 -0.1(6) . . . . ? C1 C2 C30 C31 97.0(4) . . . . ? C42 C41 C46 C45 -0.2(6) . . . . ? C27 C26 C25 I3 179.9(3) . . . . ? C27 C26 C25 C24 0.0(6) . . . . ? C46 C41 C42 C43 0.3(6) . . . . ? C16 C15 C20 C19 0.6(6) . . . . ? C58 C57 C56 C55 0.5(6) . . . . ? C58 C59 C60 C55 -0.9(6) . . . . ? C38 C37 C63 C64 85.3(4) . . . . ? C38 C39 C34 C35 10.7(5) . . . . ? C38 C39 C34 C40 -163.2(3) . . . . ? C38 C39 C65 C66 84.4(4) . . . . ? C40 O4 C41 C42 -13.0(5) . . . . ? C40 O4 C41 C46 167.4(3) . . . . ? C30 C2 C1 C7 5.4(5) . . . . ? C30 C2 C1 C6 -176.4(3) . . . . ? C34 C35 C61 C62 -91.7(4) . . . . ? C34 C39 C38 C54 168.2(3) . . . . ? C34 C39 C38 C37 -6.2(5) . . . . ? C34 C39 C65 C66 -96.2(4) . . . . ? C9 C8 C13 C12 0.5(6) . . . . ? C12 C11 C10 C9 -0.9(6) . . . . ? C6 C5 C4 C3 4.7(5) . . . . ? C6 C5 C4 C32 -175.5(3) . . . . ? C6 C5 C21 O3 86.2(4) . . . . ? C43 C44 C45 C46 0.6(6) . . . . ? C10 C11 C12 C13 0.9(6) . . . . ? C24 C23 C22 O3 -178.2(4) . . . . ? C24 C23 C22 C27 -0.5(6) . . . . ? C53 C48 C49 C50 0.7(5) . . . . ? C56 C55 C60 C59 1.8(6) . . . . ? C56 C57 C58 I6 -177.3(3) . . . . ? C56 C57 C58 C59 0.3(6) . . . . ? C65 C39 C38 C54 -12.4(5) . . . . ? C65 C39 C38 C37 173.1(3) . . . . ? C65 C39 C34 C35 -168.6(3) . . . . ? C65 C39 C34 C40 17.5(5) . . . . ? C45 C44 C43 C42 -0.5(6) . . . . ? C29 C28 C6 C5 97.7(4) . . . . ? C29 C28 C6 C1 -80.4(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962417' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-gf-154K _audit_creation_date 2013-12-25 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C33 H33 I3 O3' _chemical_formula_sum 'C33 H33 I3 O3' _chemical_formula_weight 858.29 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.4896(6) _cell_length_b 13.3369(3) _cell_length_c 26.3205(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.892(3) _cell_angle_gamma 90.00 _cell_volume 6473.0(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4954 _cell_measurement_temperature 154(2) _cell_measurement_theta_max 29.1584 _cell_measurement_theta_min 3.6320 _exptl_absorpt_coefficient_mu 2.928 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.58210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 3312 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.07 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_unetI/netI 0.0754 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 30368 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.22 _diffrn_reflns_theta_min 3.64 _diffrn_ambient_temperature 154(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.840 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0348072000 _diffrn_orient_matrix_UB_12 0.0215571000 _diffrn_orient_matrix_UB_13 -0.0119245000 _diffrn_orient_matrix_UB_21 -0.0089626000 _diffrn_orient_matrix_UB_22 -0.0111244000 _diffrn_orient_matrix_UB_23 0.0234438000 _diffrn_orient_matrix_UB_31 0.0137157000 _diffrn_orient_matrix_UB_32 0.0473210000 _diffrn_orient_matrix_UB_33 0.0109326000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 9568 _reflns_number_total 14787 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.916 _refine_diff_density_min -1.588 _refine_diff_density_rms 0.136 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 14787 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0504 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0899 _refine_ls_wR_factor_ref 0.1090 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C47(H47A,H47B), C54(H54A,H54B), C14(H14A,H14B), C21(H21A,H21B), C63(H63A,H63B), C28(H28A,H28B), C61(H61A,H61B), C40(H40A,H40B), C30(H30A,H30B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C26(H26), C49(H49), C52(H52), C19(H19), C57(H57), C23(H23), C20(H20), C59(H59), C13(H13), C50(H50), C17(H17), C60(H60), C42(H42), C27(H27), C46(H46), C16(H16), C9(H9), C12(H12), C43(H43), C10(H10), C24(H24), C53(H53), C56(H56), C45(H45) 2.c Idealised Me refined as rotating group: C62(H62A,H62B,H62C), C64(H64A,H64B,H64C), C33(H33A,H33B,H33C), C31(H31A,H31B, H31C), C66(H66A,H66B,H66C), C29(H29A,H29B,H29C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I5 I 0.54226(2) 0.69188(3) 0.286500(15) 0.03822(11) Uani 1 1 d . . . I2 I -0.03456(2) 0.30532(3) 0.726826(15) 0.03927(11) Uani 1 1 d . . . I6 I 0.32723(2) 0.45232(3) 0.775089(15) 0.04131(11) Uani 1 1 d . . . I3 I 0.17022(2) 0.56478(3) 0.211895(15) 0.04401(12) Uani 1 1 d . . . I4 I -0.01998(2) 1.54288(3) 0.40982(2) 0.05148(13) Uani 1 1 d . . . I1 I 0.52887(2) -0.52367(3) 0.59443(2) 0.05827(15) Uani 1 1 d . . . O2 O 0.17676(17) 0.1869(3) 0.60288(13) 0.0282(8) Uani 1 1 d . . . O3 O 0.23561(18) 0.2775(3) 0.40848(14) 0.0317(9) Uani 1 1 d . . . O1 O 0.40908(17) -0.0865(2) 0.56886(13) 0.0263(8) Uani 1 1 d . . . O6 O 0.23612(18) 0.7171(3) 0.56877(13) 0.0297(8) Uani 1 1 d . . . O5 O 0.31365(17) 0.8233(3) 0.39322(13) 0.0266(8) Uani 1 1 d . . . C7 C 0.3410(3) -0.0646(4) 0.5280(2) 0.0251(11) Uani 1 1 d . . . H7A H 0.3023 -0.1079 0.5328 0.030 Uiso 1 1 calc . . R H7B H 0.3448 -0.0780 0.4920 0.030 Uiso 1 1 calc . . R C26 C 0.1376(3) 0.4163(4) 0.2892(2) 0.0322(13) Uani 1 1 d . . . H26 H 0.0888 0.4245 0.2668 0.039 Uiso 1 1 calc . . R C8 C 0.4322(2) -0.1840(4) 0.57181(19) 0.0225(11) Uani 1 1 d . . . O4 O 0.06036(17) 1.0892(2) 0.41760(13) 0.0269(8) Uani 1 1 d . . . C3 C 0.2819(2) 0.1775(4) 0.57884(19) 0.0218(11) Uani 1 1 d . . . C36 C 0.2005(2) 0.8270(4) 0.40871(19) 0.0230(11) Uani 1 1 d . . . C48 C 0.3605(3) 0.7939(4) 0.3668(2) 0.0231(11) Uani 1 1 d . . . C25 C 0.1930(3) 0.4682(4) 0.2781(2) 0.0333(13) Uani 1 1 d . . . C51 C 0.4645(3) 0.7398(4) 0.3209(2) 0.0259(12) Uani 1 1 d . . . C47 C 0.2371(3) 0.8013(4) 0.3681(2) 0.0259(12) Uani 1 1 d . . . H47A H 0.2301 0.7295 0.3583 0.031 Uiso 1 1 calc . . R H47B H 0.2168 0.8421 0.3352 0.031 Uiso 1 1 calc . . R C54 C 0.1658(3) 0.7039(4) 0.5280(2) 0.0273(12) Uani 1 1 d . . . H54A H 0.1263 0.7171 0.5431 0.033 Uiso 1 1 calc . . R H54B H 0.1605 0.6347 0.5136 0.033 Uiso 1 1 calc . . R C49 C 0.3396(3) 0.7477(4) 0.3169(2) 0.0269(12) Uani 1 1 d . . . H49 H 0.2898 0.7346 0.2985 0.032 Uiso 1 1 calc . . R C35 C 0.1722(2) 0.9241(4) 0.40996(19) 0.0220(11) Uani 1 1 d . . . C2 C 0.3045(2) 0.0774(4) 0.57708(19) 0.0213(11) Uani 1 1 d . . . C37 C 0.2001(2) 0.7555(3) 0.44771(19) 0.0201(11) Uani 1 1 d . . . C5 C 0.3024(3) 0.2119(4) 0.4947(2) 0.0237(11) Uani 1 1 d . . . C18 C 0.0393(3) 0.2597(4) 0.6884(2) 0.0243(11) Uani 1 1 d . . . C4 C 0.2795(2) 0.2450(4) 0.53722(19) 0.0224(11) Uani 1 1 d . . . C41 C 0.0454(3) 1.1896(4) 0.4185(2) 0.0230(11) Uani 1 1 d . . . C55 C 0.2527(3) 0.6556(4) 0.6130(2) 0.0246(11) Uani 1 1 d . . . C14 C 0.2532(3) 0.2097(4) 0.6231(2) 0.0263(12) Uani 1 1 d . . . H14A H 0.2773 0.1721 0.6565 0.032 Uiso 1 1 calc . . R H14B H 0.2612 0.2823 0.6304 0.032 Uiso 1 1 calc . . R C52 C 0.4856(3) 0.7876(4) 0.3704(2) 0.0296(12) Uani 1 1 d . . . H52 H 0.5353 0.8020 0.3886 0.036 Uiso 1 1 calc . . R C15 C 0.1347(3) 0.2116(4) 0.63444(19) 0.0219(11) Uani 1 1 d . . . C19 C 0.0137(3) 0.2119(4) 0.6392(2) 0.0257(12) Uani 1 1 d . . . H19 H -0.0363 0.1958 0.6241 0.031 Uiso 1 1 calc . . R C21 C 0.3043(3) 0.2843(4) 0.4510(2) 0.0279(12) Uani 1 1 d . . . H21A H 0.3122 0.3535 0.4654 0.033 Uiso 1 1 calc . . R H21B H 0.3444 0.2668 0.4372 0.033 Uiso 1 1 calc . . R C57 C 0.3456(3) 0.6002(4) 0.6929(2) 0.0325(13) Uani 1 1 d . . . H57 H 0.3943 0.6024 0.7163 0.039 Uiso 1 1 calc . . R C23 C 0.2802(3) 0.3927(4) 0.3546(2) 0.0391(14) Uani 1 1 d . . . H23 H 0.3291 0.3846 0.3770 0.047 Uiso 1 1 calc . . R C11 C 0.4889(3) -0.3755(4) 0.5848(2) 0.0339(13) Uani 1 1 d . . . C63 C 0.2370(3) 0.6551(3) 0.4497(2) 0.0261(12) Uani 1 1 d . . . H63A H 0.2583 0.6342 0.4877 0.031 Uiso 1 1 calc . . R H63B H 0.2772 0.6627 0.4347 0.031 Uiso 1 1 calc . . R C20 C 0.0621(3) 0.1878(4) 0.6120(2) 0.0256(11) Uani 1 1 d . . . H20 H 0.0452 0.1551 0.5781 0.031 Uiso 1 1 calc . . R C39 C 0.1309(2) 0.8720(4) 0.48380(19) 0.0221(11) Uani 1 1 d . . . C22 C 0.2251(3) 0.3409(4) 0.3655(2) 0.0268(12) Uani 1 1 d . . . C59 C 0.2258(3) 0.5322(4) 0.6702(2) 0.0349(14) Uani 1 1 d . . . H59 H 0.1925 0.4880 0.6782 0.042 Uiso 1 1 calc . . R C13 C 0.4057(3) -0.2539(4) 0.5316(2) 0.0301(13) Uani 1 1 d . . . H13 H 0.3679 -0.2363 0.4997 0.036 Uiso 1 1 calc . . R C50 C 0.3921(3) 0.7208(4) 0.2941(2) 0.0282(12) Uani 1 1 d . . . H50 H 0.3781 0.6891 0.2600 0.034 Uiso 1 1 calc . . R C28 C 0.3442(3) 0.0779(4) 0.4434(2) 0.0291(12) Uani 1 1 d . . . H28A H 0.3249 0.0099 0.4321 0.035 Uiso 1 1 calc . . R H28B H 0.3235 0.1240 0.4128 0.035 Uiso 1 1 calc . . R C61 C 0.1727(3) 1.0014(4) 0.3680(2) 0.0279(12) Uani 1 1 d . . . H61A H 0.2174 0.9933 0.3581 0.034 Uiso 1 1 calc . . R H61B H 0.1736 1.0694 0.3833 0.034 Uiso 1 1 calc . . R C17 C 0.1123(3) 0.2817(4) 0.7109(2) 0.0270(12) Uani 1 1 d . . . H17 H 0.1295 0.3137 0.7449 0.032 Uiso 1 1 calc . . R C60 C 0.2034(3) 0.5913(4) 0.6242(2) 0.0321(13) Uani 1 1 d . . . H60 H 0.1549 0.5876 0.6006 0.039 Uiso 1 1 calc . . R C44 C 0.0068(3) 1.3897(4) 0.4135(2) 0.0326(13) Uani 1 1 d . . . C1 C 0.3229(2) 0.0444(3) 0.53262(19) 0.0215(11) Uani 1 1 d . . . C42 C 0.0784(3) 1.2521(4) 0.4616(2) 0.0286(12) Uani 1 1 d . . . H42 H 0.1140 1.2265 0.4927 0.034 Uiso 1 1 calc . . R C27 C 0.1543(3) 0.3526(4) 0.3330(2) 0.0287(12) Uani 1 1 d . . . H27 H 0.1167 0.3167 0.3407 0.034 Uiso 1 1 calc . . R C46 C -0.0067(3) 1.2274(4) 0.3727(2) 0.0298(12) Uani 1 1 d . . . H46 H -0.0292 1.1844 0.3432 0.036 Uiso 1 1 calc . . R C16 C 0.1605(3) 0.2571(4) 0.68393(19) 0.0249(11) Uani 1 1 d . . . H16 H 0.2107 0.2716 0.6994 0.030 Uiso 1 1 calc . . R C58 C 0.2963(3) 0.5380(4) 0.7041(2) 0.0306(13) Uani 1 1 d . . . C38 C 0.1635(2) 0.7785(3) 0.48448(19) 0.0206(11) Uani 1 1 d . . . C40 C 0.1237(3) 1.0553(4) 0.4586(2) 0.0263(12) Uani 1 1 d . . . H40A H 0.1165 1.0617 0.4940 0.032 Uiso 1 1 calc . . R H40B H 0.1655 1.0979 0.4589 0.032 Uiso 1 1 calc . . R C30 C 0.3101(3) 0.0066(4) 0.62409(19) 0.0269(12) Uani 1 1 d . . . H30A H 0.2690 0.0196 0.6375 0.032 Uiso 1 1 calc . . R H30B H 0.3061 -0.0635 0.6111 0.032 Uiso 1 1 calc . . R C34 C 0.1404(2) 0.9467(3) 0.4495(2) 0.0227(11) Uani 1 1 d . . . C9 C 0.4877(3) -0.2103(4) 0.6185(2) 0.0311(13) Uani 1 1 d . . . H9 H 0.5065 -0.1619 0.6460 0.037 Uiso 1 1 calc . . R C32 C 0.2538(3) 0.3522(4) 0.5383(2) 0.0282(12) Uani 1 1 d . . . H32A H 0.2176 0.3539 0.5573 0.034 Uiso 1 1 calc . . R H32B H 0.2296 0.3749 0.5009 0.034 Uiso 1 1 calc . . R C62 C 0.1065(3) 0.9917(5) 0.3175(2) 0.0411(15) Uani 1 1 d . . . H62A H 0.0623 1.0039 0.3266 0.062 Uiso 1 1 calc . . GR H62B H 0.1049 0.9239 0.3027 0.062 Uiso 1 1 calc . . GR H62C H 0.1098 1.0409 0.2907 0.062 Uiso 1 1 calc . . GR C12 C 0.4346(3) -0.3507(4) 0.5380(2) 0.0344(13) Uani 1 1 d . . . H12 H 0.4169 -0.3990 0.5103 0.041 Uiso 1 1 calc . . R C6 C 0.3219(2) 0.1119(4) 0.4912(2) 0.0231(11) Uani 1 1 d . . . C43 C 0.0586(3) 1.3532(4) 0.4589(2) 0.0338(13) Uani 1 1 d . . . H43 H 0.0807 1.3966 0.4882 0.041 Uiso 1 1 calc . . R C10 C 0.5153(3) -0.3062(4) 0.6248(2) 0.0344(13) Uani 1 1 d . . . H10 H 0.5527 -0.3243 0.6569 0.041 Uiso 1 1 calc . . R C24 C 0.2635(3) 0.4565(4) 0.3109(2) 0.0381(14) Uani 1 1 d . . . H24 H 0.3012 0.4927 0.3034 0.046 Uiso 1 1 calc . . R C64 C 0.1860(3) 0.5732(4) 0.4188(2) 0.0386(14) Uani 1 1 d . . . H64A H 0.1459 0.5652 0.4334 0.058 Uiso 1 1 calc . . GR H64B H 0.2126 0.5098 0.4224 0.058 Uiso 1 1 calc . . GR H64C H 0.1666 0.5917 0.3808 0.058 Uiso 1 1 calc . . GR C33 C 0.3152(3) 0.4247(4) 0.5656(2) 0.0405(15) Uani 1 1 d . . . H33A H 0.3521 0.4220 0.5477 0.061 Uiso 1 1 calc . . GR H33B H 0.3371 0.4058 0.6034 0.061 Uiso 1 1 calc . . GR H33C H 0.2958 0.4930 0.5634 0.061 Uiso 1 1 calc . . GR C53 C 0.4330(3) 0.8138(4) 0.3929(2) 0.0292(12) Uani 1 1 d . . . H53 H 0.4470 0.8462 0.4269 0.035 Uiso 1 1 calc . . R C56 C 0.3241(3) 0.6602(4) 0.6469(2) 0.0290(12) Uani 1 1 d . . . H56 H 0.3579 0.7037 0.6388 0.035 Uiso 1 1 calc . . R C65 C 0.0844(3) 0.8933(4) 0.51936(19) 0.0275(12) Uani 1 1 d . . . H65A H 0.0494 0.9468 0.5022 0.033 Uiso 1 1 calc . . R H65B H 0.0562 0.8322 0.5206 0.033 Uiso 1 1 calc . . R C45 C -0.0252(3) 1.3272(4) 0.3704(2) 0.0340(13) Uani 1 1 d . . . H45 H -0.0603 1.3533 0.3391 0.041 Uiso 1 1 calc . . R C31 C 0.3808(3) 0.0187(4) 0.6701(2) 0.0405(15) Uani 1 1 d . . . H31A H 0.4217 0.0059 0.6571 0.061 Uiso 1 1 calc . . GR H31B H 0.3821 -0.0292 0.6986 0.061 Uiso 1 1 calc . . GR H31C H 0.3842 0.0871 0.6843 0.061 Uiso 1 1 calc . . GR C66 C 0.1250(3) 0.9250(4) 0.5766(2) 0.0343(13) Uani 1 1 d . . . H66A H 0.1589 0.8719 0.5946 0.051 Uiso 1 1 calc . . GR H66B H 0.0903 0.9367 0.5958 0.051 Uiso 1 1 calc . . GR H66C H 0.1520 0.9868 0.5762 0.051 Uiso 1 1 calc . . GR C29 C 0.4265(3) 0.0768(5) 0.4583(2) 0.0474(16) Uani 1 1 d . . . H29A H 0.4402 0.0488 0.4285 0.071 Uiso 1 1 calc . . GR H29B H 0.4472 0.0354 0.4904 0.071 Uiso 1 1 calc . . GR H29C H 0.4451 0.1454 0.4656 0.071 Uiso 1 1 calc . . GR 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 I5 0.0334(2) 0.0487(2) 0.0385(2) -0.0076(2) 0.01988(17) 0.00274(18) I2 0.0374(2) 0.0522(2) 0.0337(2) -0.0066(2) 0.01908(17) 0.00356(19) I6 0.0478(2) 0.0487(2) 0.0261(2) 0.01210(19) 0.01010(17) 0.0131(2) I3 0.0508(3) 0.0531(3) 0.0298(2) 0.0132(2) 0.01535(18) 0.0172(2) I4 0.0346(2) 0.02160(18) 0.0906(4) 0.0133(2) 0.0097(2) 0.00611(17) I1 0.0389(2) 0.0251(2) 0.1018(4) 0.0168(2) 0.0103(2) 0.00957(18) O2 0.0230(18) 0.035(2) 0.030(2) -0.0138(18) 0.0121(15) -0.0038(16) O3 0.028(2) 0.032(2) 0.031(2) 0.0068(18) 0.0030(16) -0.0035(17) O1 0.0240(19) 0.0201(18) 0.030(2) -0.0026(17) 0.0012(15) 0.0036(15) O6 0.0280(19) 0.031(2) 0.027(2) 0.0087(18) 0.0042(16) -0.0046(17) O5 0.0239(18) 0.033(2) 0.0246(19) -0.0086(17) 0.0106(15) 0.0013(16) C7 0.026(3) 0.022(3) 0.024(3) 0.003(2) 0.003(2) 0.002(2) C26 0.034(3) 0.036(3) 0.022(3) -0.003(3) 0.001(2) -0.003(3) C8 0.020(2) 0.025(3) 0.024(3) 0.003(2) 0.009(2) 0.002(2) O4 0.0228(18) 0.0187(17) 0.035(2) -0.0008(17) 0.0029(15) 0.0045(15) C3 0.018(2) 0.025(3) 0.020(3) -0.005(2) 0.002(2) -0.001(2) C36 0.018(2) 0.030(3) 0.021(3) -0.001(2) 0.007(2) 0.005(2) C48 0.025(3) 0.022(3) 0.024(3) 0.004(2) 0.011(2) 0.004(2) C25 0.038(3) 0.034(3) 0.027(3) 0.002(3) 0.010(3) 0.007(3) C51 0.030(3) 0.022(3) 0.033(3) 0.001(3) 0.019(2) 0.004(2) C47 0.022(3) 0.028(3) 0.027(3) 0.001(2) 0.007(2) 0.004(2) C54 0.024(3) 0.024(3) 0.031(3) 0.002(3) 0.006(2) -0.004(2) C49 0.024(3) 0.030(3) 0.025(3) -0.001(3) 0.005(2) -0.002(2) C35 0.020(2) 0.022(3) 0.025(3) 0.004(2) 0.007(2) -0.003(2) C2 0.014(2) 0.024(3) 0.027(3) -0.002(2) 0.008(2) 0.000(2) C37 0.019(2) 0.015(2) 0.025(3) -0.003(2) 0.005(2) 0.002(2) C5 0.021(3) 0.021(3) 0.028(3) 0.006(2) 0.008(2) 0.000(2) C18 0.028(3) 0.024(3) 0.025(3) 0.003(2) 0.014(2) 0.008(2) C4 0.022(3) 0.021(3) 0.023(3) 0.000(2) 0.005(2) 0.002(2) C41 0.020(2) 0.021(3) 0.031(3) 0.000(3) 0.013(2) 0.003(2) C55 0.027(3) 0.016(2) 0.027(3) 0.005(2) 0.005(2) 0.003(2) C14 0.021(3) 0.025(3) 0.030(3) -0.006(2) 0.006(2) -0.003(2) C52 0.029(3) 0.031(3) 0.031(3) -0.003(3) 0.012(2) -0.003(2) C15 0.028(3) 0.020(2) 0.019(3) 0.000(2) 0.010(2) 0.001(2) C19 0.022(3) 0.026(3) 0.027(3) -0.003(2) 0.006(2) 0.002(2) C21 0.027(3) 0.024(3) 0.035(3) 0.002(3) 0.012(2) 0.001(2) C57 0.028(3) 0.039(3) 0.024(3) -0.008(3) 0.000(2) -0.002(3) C23 0.028(3) 0.041(3) 0.048(4) 0.019(3) 0.011(3) 0.008(3) C11 0.035(3) 0.022(3) 0.045(4) 0.009(3) 0.013(3) 0.005(3) C63 0.031(3) 0.017(2) 0.029(3) -0.002(2) 0.007(2) 0.003(2) C20 0.026(3) 0.026(3) 0.023(3) -0.007(2) 0.006(2) -0.002(2) C39 0.020(2) 0.020(2) 0.026(3) -0.003(2) 0.008(2) -0.007(2) C22 0.033(3) 0.021(3) 0.027(3) 0.004(2) 0.011(2) 0.009(2) C59 0.030(3) 0.040(3) 0.036(3) 0.013(3) 0.014(3) 0.004(3) C13 0.024(3) 0.031(3) 0.028(3) 0.002(3) -0.002(2) 0.006(2) C50 0.036(3) 0.026(3) 0.022(3) 0.000(2) 0.009(2) 0.004(2) C28 0.032(3) 0.030(3) 0.026(3) 0.001(3) 0.011(2) 0.004(2) C61 0.030(3) 0.025(3) 0.032(3) 0.010(3) 0.014(2) 0.006(2) C17 0.030(3) 0.028(3) 0.019(3) -0.003(2) 0.003(2) 0.004(2) C60 0.023(3) 0.039(3) 0.032(3) 0.010(3) 0.006(2) -0.004(3) C44 0.028(3) 0.021(3) 0.050(4) 0.005(3) 0.015(3) 0.003(2) C1 0.020(2) 0.019(2) 0.024(3) 0.001(2) 0.005(2) 0.001(2) C42 0.026(3) 0.021(3) 0.035(3) 0.003(3) 0.006(2) 0.008(2) C27 0.025(3) 0.029(3) 0.031(3) -0.007(3) 0.007(2) -0.006(2) C46 0.031(3) 0.031(3) 0.028(3) -0.002(3) 0.009(2) 0.000(3) C16 0.020(3) 0.027(3) 0.025(3) 0.001(2) 0.002(2) 0.005(2) C58 0.039(3) 0.033(3) 0.024(3) 0.007(3) 0.017(2) 0.007(3) C38 0.021(2) 0.018(2) 0.018(3) 0.003(2) 0.002(2) -0.002(2) C40 0.025(3) 0.021(3) 0.031(3) 0.004(2) 0.006(2) 0.004(2) C30 0.032(3) 0.029(3) 0.024(3) 0.002(3) 0.015(2) -0.005(2) C34 0.018(2) 0.018(2) 0.030(3) 0.002(2) 0.004(2) 0.000(2) C9 0.032(3) 0.034(3) 0.026(3) 0.000(3) 0.007(2) -0.003(3) C32 0.026(3) 0.021(3) 0.035(3) 0.003(3) 0.007(2) 0.004(2) C62 0.046(4) 0.043(4) 0.037(3) 0.016(3) 0.017(3) 0.010(3) C12 0.032(3) 0.023(3) 0.042(4) -0.003(3) 0.004(3) -0.001(2) C6 0.017(2) 0.023(3) 0.029(3) 0.003(2) 0.006(2) 0.003(2) C43 0.030(3) 0.024(3) 0.044(4) -0.003(3) 0.006(3) 0.004(2) C10 0.030(3) 0.037(3) 0.034(3) 0.016(3) 0.009(2) 0.009(3) C24 0.034(3) 0.043(3) 0.041(4) 0.014(3) 0.016(3) 0.007(3) C64 0.043(3) 0.024(3) 0.044(4) -0.005(3) 0.008(3) -0.001(3) C33 0.043(4) 0.025(3) 0.050(4) -0.008(3) 0.009(3) -0.004(3) C53 0.030(3) 0.029(3) 0.031(3) -0.007(3) 0.013(2) -0.003(2) C56 0.030(3) 0.029(3) 0.026(3) 0.000(3) 0.006(2) -0.009(2) C65 0.030(3) 0.025(3) 0.029(3) -0.003(3) 0.010(2) 0.000(2) C45 0.032(3) 0.033(3) 0.037(3) 0.014(3) 0.012(3) 0.010(3) C31 0.042(3) 0.040(3) 0.034(3) 0.006(3) 0.004(3) 0.006(3) C66 0.037(3) 0.038(3) 0.030(3) -0.009(3) 0.013(2) -0.008(3) C29 0.038(3) 0.059(4) 0.050(4) 0.001(4) 0.021(3) 0.006(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 I5 C51 2.100(5) . ? I2 C18 2.100(5) . ? I6 C58 2.105(5) . ? I3 C25 2.096(5) . ? I4 C44 2.103(5) . ? I1 C11 2.109(5) . ? O2 C14 1.443(5) . ? O2 C15 1.382(5) . ? O3 C21 1.444(6) . ? O3 C22 1.374(6) . ? O1 C7 1.442(5) . ? O1 C8 1.370(6) . ? O6 C54 1.452(5) . ? O6 C55 1.375(6) . ? O5 C48 1.372(5) . ? O5 C47 1.452(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C1 1.510(6) . ? C26 H26 0.9500 . ? C26 C25 1.390(7) . ? C26 C27 1.384(7) . ? C8 C13 1.378(7) . ? C8 C9 1.393(7) . ? O4 C41 1.372(5) . ? O4 C40 1.425(5) . ? C3 C2 1.411(6) . ? C3 C4 1.407(7) . ? C3 C14 1.508(6) . ? C36 C47 1.503(6) . ? C36 C35 1.412(7) . ? C36 C37 1.403(7) . ? C48 C49 1.386(7) . ? C48 C53 1.382(7) . ? C25 C24 1.374(7) . ? C51 C52 1.390(7) . ? C51 C50 1.381(7) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C54 C38 1.507(6) . ? C49 H49 0.9500 . ? C49 C50 1.391(7) . ? C35 C61 1.515(6) . ? C35 C34 1.407(6) . ? C2 C1 1.401(6) . ? C2 C30 1.531(7) . ? C37 C63 1.513(6) . ? C37 C38 1.409(6) . ? C5 C4 1.404(6) . ? C5 C21 1.511(7) . ? C5 C6 1.398(6) . ? C18 C19 1.384(7) . ? C18 C17 1.384(7) . ? C4 C32 1.517(6) . ? C41 C42 1.387(7) . ? C41 C46 1.395(7) . ? C55 C60 1.388(7) . ? C55 C56 1.390(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C52 H52 0.9500 . ? C52 C53 1.385(7) . ? C15 C20 1.383(6) . ? C15 C16 1.376(6) . ? C19 H19 0.9500 . ? C19 C20 1.394(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C57 H57 0.9500 . ? C57 C58 1.372(7) . ? C57 C56 1.398(7) . ? C23 H23 0.9500 . ? C23 C22 1.383(7) . ? C23 C24 1.383(7) . ? C11 C12 1.379(7) . ? C11 C10 1.371(8) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C63 C64 1.524(7) . ? C20 H20 0.9500 . ? C39 C38 1.397(6) . ? C39 C34 1.396(6) . ? C39 C65 1.524(6) . ? C22 C27 1.377(7) . ? C59 H59 0.9500 . ? C59 C60 1.391(7) . ? C59 C58 1.378(7) . ? C13 H13 0.9500 . ? C13 C12 1.396(7) . ? C50 H50 0.9500 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C6 1.528(6) . ? C28 C29 1.522(7) . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C61 C62 1.529(7) . ? C17 H17 0.9500 . ? C17 C16 1.387(7) . ? C60 H60 0.9500 . ? C44 C43 1.379(7) . ? C44 C45 1.382(8) . ? C1 C6 1.410(7) . ? C42 H42 0.9500 . ? C42 C43 1.397(7) . ? C27 H27 0.9500 . ? C46 H46 0.9500 . ? C46 C45 1.375(7) . ? C16 H16 0.9500 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C40 C34 1.519(6) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 C31 1.520(7) . ? C9 H9 0.9500 . ? C9 C10 1.377(7) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C33 1.526(7) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C12 H12 0.9500 . ? C43 H43 0.9500 . ? C10 H10 0.9500 . ? C24 H24 0.9500 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C53 H53 0.9500 . ? C56 H56 0.9500 . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C65 C66 1.516(7) . ? C45 H45 0.9500 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O2 C14 118.1(4) . . ? C22 O3 C21 117.0(4) . . ? C8 O1 C7 116.1(4) . . ? C55 O6 C54 117.4(4) . . ? C48 O5 C47 117.8(4) . . ? O1 C7 H7A 110.0 . . ? O1 C7 H7B 110.0 . . ? O1 C7 C1 108.5(4) . . ? H7A C7 H7B 108.4 . . ? C1 C7 H7A 110.0 . . ? C1 C7 H7B 110.0 . . ? C25 C26 H26 120.3 . . ? C27 C26 H26 120.3 . . ? C27 C26 C25 119.5(5) . . ? O1 C8 C13 124.3(4) . . ? O1 C8 C9 115.8(4) . . ? C13 C8 C9 119.8(5) . . ? C41 O4 C40 115.7(4) . . ? C2 C3 C14 119.5(4) . . ? C4 C3 C2 120.8(4) . . ? C4 C3 C14 119.4(4) . . ? C35 C36 C47 120.3(4) . . ? C37 C36 C47 118.8(4) . . ? C37 C36 C35 120.8(4) . . ? O5 C48 C49 124.5(4) . . ? O5 C48 C53 115.7(4) . . ? C53 C48 C49 119.8(5) . . ? C26 C25 I3 120.7(4) . . ? C24 C25 I3 119.4(4) . . ? C24 C25 C26 119.9(5) . . ? C52 C51 I5 120.5(4) . . ? C50 C51 I5 119.0(4) . . ? C50 C51 C52 120.4(5) . . ? O5 C47 C36 106.6(4) . . ? O5 C47 H47A 110.4 . . ? O5 C47 H47B 110.4 . . ? C36 C47 H47A 110.4 . . ? C36 C47 H47B 110.4 . . ? H47A C47 H47B 108.6 . . ? O6 C54 H54A 110.6 . . ? O6 C54 H54B 110.6 . . ? O6 C54 C38 105.7(4) . . ? H54A C54 H54B 108.7 . . ? C38 C54 H54A 110.6 . . ? C38 C54 H54B 110.6 . . ? C48 C49 H49 120.3 . . ? C48 C49 C50 119.4(5) . . ? C50 C49 H49 120.3 . . ? C36 C35 C61 120.8(4) . . ? C34 C35 C36 118.9(4) . . ? C34 C35 C61 120.2(4) . . ? C3 C2 C30 119.9(4) . . ? C1 C2 C3 119.5(4) . . ? C1 C2 C30 120.7(4) . . ? C36 C37 C63 120.8(4) . . ? C36 C37 C38 118.6(4) . . ? C38 C37 C63 120.6(4) . . ? C4 C5 C21 119.9(4) . . ? C6 C5 C4 121.1(5) . . ? C6 C5 C21 119.0(4) . . ? C19 C18 I2 119.2(4) . . ? C17 C18 I2 120.2(4) . . ? C17 C18 C19 120.5(4) . . ? C3 C4 C32 121.1(4) . . ? C5 C4 C3 118.7(4) . . ? C5 C4 C32 120.1(4) . . ? O4 C41 C42 123.8(4) . . ? O4 C41 C46 115.9(4) . . ? C42 C41 C46 120.3(5) . . ? O6 C55 C60 124.0(4) . . ? O6 C55 C56 115.3(4) . . ? C60 C55 C56 120.7(5) . . ? O2 C14 C3 104.6(4) . . ? O2 C14 H14A 110.8 . . ? O2 C14 H14B 110.8 . . ? C3 C14 H14A 110.8 . . ? C3 C14 H14B 110.8 . . ? H14A C14 H14B 108.9 . . ? C51 C52 H52 120.6 . . ? C53 C52 C51 118.8(5) . . ? C53 C52 H52 120.6 . . ? O2 C15 C20 114.4(4) . . ? C16 C15 O2 124.7(4) . . ? C16 C15 C20 121.0(5) . . ? C18 C19 H19 120.4 . . ? C18 C19 C20 119.2(5) . . ? C20 C19 H19 120.4 . . ? O3 C21 C5 107.7(4) . . ? O3 C21 H21A 110.2 . . ? O3 C21 H21B 110.2 . . ? C5 C21 H21A 110.2 . . ? C5 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C58 C57 H57 120.0 . . ? C58 C57 C56 119.9(5) . . ? C56 C57 H57 120.0 . . ? C22 C23 H23 120.3 . . ? C22 C23 C24 119.4(5) . . ? C24 C23 H23 120.3 . . ? C12 C11 I1 118.7(4) . . ? C10 C11 I1 120.5(4) . . ? C10 C11 C12 120.8(5) . . ? C37 C63 H63A 108.9 . . ? C37 C63 H63B 108.9 . . ? C37 C63 C64 113.3(4) . . ? H63A C63 H63B 107.7 . . ? C64 C63 H63A 108.9 . . ? C64 C63 H63B 108.9 . . ? C15 C20 C19 119.8(5) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C38 C39 C65 121.2(4) . . ? C34 C39 C38 119.3(4) . . ? C34 C39 C65 119.5(4) . . ? O3 C22 C23 124.0(5) . . ? O3 C22 C27 115.7(5) . . ? C27 C22 C23 120.3(5) . . ? C60 C59 H59 120.0 . . ? C58 C59 H59 120.0 . . ? C58 C59 C60 119.9(5) . . ? C8 C13 H13 120.1 . . ? C8 C13 C12 119.7(5) . . ? C12 C13 H13 120.1 . . ? C51 C50 C49 120.4(5) . . ? C51 C50 H50 119.8 . . ? C49 C50 H50 119.8 . . ? H28A C28 H28B 108.1 . . ? C6 C28 H28A 109.6 . . ? C6 C28 H28B 109.6 . . ? C29 C28 H28A 109.6 . . ? C29 C28 H28B 109.6 . . ? C29 C28 C6 110.3(4) . . ? C35 C61 H61A 109.2 . . ? C35 C61 H61B 109.2 . . ? C35 C61 C62 111.9(4) . . ? H61A C61 H61B 107.9 . . ? C62 C61 H61A 109.2 . . ? C62 C61 H61B 109.2 . . ? C18 C17 H17 119.9 . . ? C18 C17 C16 120.2(5) . . ? C16 C17 H17 119.9 . . ? C55 C60 C59 119.4(5) . . ? C55 C60 H60 120.3 . . ? C59 C60 H60 120.3 . . ? C43 C44 I4 118.9(4) . . ? C43 C44 C45 120.5(5) . . ? C45 C44 I4 120.6(4) . . ? C2 C1 C7 120.0(4) . . ? C2 C1 C6 120.1(4) . . ? C6 C1 C7 119.8(4) . . ? C41 C42 H42 120.3 . . ? C41 C42 C43 119.4(5) . . ? C43 C42 H42 120.3 . . ? C26 C27 H27 119.9 . . ? C22 C27 C26 120.3(5) . . ? C22 C27 H27 119.9 . . ? C41 C46 H46 120.2 . . ? C45 C46 C41 119.6(5) . . ? C45 C46 H46 120.2 . . ? C15 C16 C17 119.3(5) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C57 C58 I6 120.0(4) . . ? C57 C58 C59 121.0(5) . . ? C59 C58 I6 119.0(4) . . ? C37 C38 C54 118.7(4) . . ? C39 C38 C54 120.0(4) . . ? C39 C38 C37 121.0(4) . . ? O4 C40 H40A 109.4 . . ? O4 C40 H40B 109.4 . . ? O4 C40 C34 111.1(4) . . ? H40A C40 H40B 108.0 . . ? C34 C40 H40A 109.4 . . ? C34 C40 H40B 109.4 . . ? C2 C30 H30A 109.0 . . ? C2 C30 H30B 109.0 . . ? H30A C30 H30B 107.8 . . ? C31 C30 C2 112.8(4) . . ? C31 C30 H30A 109.0 . . ? C31 C30 H30B 109.0 . . ? C35 C34 C40 119.2(4) . . ? C39 C34 C35 120.5(4) . . ? C39 C34 C40 120.0(4) . . ? C8 C9 H9 119.9 . . ? C10 C9 C8 120.1(5) . . ? C10 C9 H9 119.9 . . ? C4 C32 H32A 108.9 . . ? C4 C32 H32B 108.9 . . ? C4 C32 C33 113.2(4) . . ? H32A C32 H32B 107.8 . . ? C33 C32 H32A 108.9 . . ? C33 C32 H32B 108.9 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C11 C12 C13 119.5(5) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C5 C6 C28 119.6(4) . . ? C5 C6 C1 119.6(4) . . ? C1 C6 C28 120.8(4) . . ? C44 C43 C42 119.8(5) . . ? C44 C43 H43 120.1 . . ? C42 C43 H43 120.1 . . ? C11 C10 C9 119.9(5) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.0 . . ? C25 C24 C23 120.7(5) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C48 C53 C52 121.3(5) . . ? C48 C53 H53 119.4 . . ? C52 C53 H53 119.4 . . ? C55 C56 C57 119.1(5) . . ? C55 C56 H56 120.5 . . ? C57 C56 H56 120.5 . . ? C39 C65 H65A 108.3 . . ? C39 C65 H65B 108.3 . . ? H65A C65 H65B 107.4 . . ? C66 C65 C39 116.1(4) . . ? C66 C65 H65A 108.3 . . ? C66 C65 H65B 108.3 . . ? C44 C45 H45 119.8 . . ? C46 C45 C44 120.4(5) . . ? C46 C45 H45 119.8 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I5 C51 C52 C53 -177.0(4) . . . . ? I5 C51 C50 C49 177.2(4) . . . . ? I2 C18 C19 C20 175.7(4) . . . . ? I2 C18 C17 C16 -176.0(4) . . . . ? I3 C25 C24 C23 -179.5(4) . . . . ? I4 C44 C43 C42 -178.6(4) . . . . ? I4 C44 C45 C46 179.0(4) . . . . ? I1 C11 C12 C13 177.8(4) . . . . ? I1 C11 C10 C9 -178.6(4) . . . . ? O2 C15 C20 C19 -177.9(4) . . . . ? O2 C15 C16 C17 177.5(4) . . . . ? O3 C22 C27 C26 178.8(5) . . . . ? O1 C7 C1 C2 -68.9(6) . . . . ? O1 C7 C1 C6 113.4(5) . . . . ? O1 C8 C13 C12 178.0(5) . . . . ? O1 C8 C9 C10 -179.0(4) . . . . ? O6 C54 C38 C37 78.9(5) . . . . ? O6 C54 C38 C39 -95.7(5) . . . . ? O6 C55 C60 C59 -179.9(5) . . . . ? O6 C55 C56 C57 179.9(5) . . . . ? O5 C48 C49 C50 -179.7(4) . . . . ? O5 C48 C53 C52 179.8(4) . . . . ? C7 O1 C8 C13 16.9(7) . . . . ? C7 O1 C8 C9 -165.2(4) . . . . ? C7 C1 C6 C5 177.5(4) . . . . ? C7 C1 C6 C28 -4.3(7) . . . . ? C26 C25 C24 C23 0.7(8) . . . . ? C8 O1 C7 C1 177.3(4) . . . . ? C8 C13 C12 C11 0.7(8) . . . . ? C8 C9 C10 C11 1.0(8) . . . . ? O4 C41 C42 C43 -179.1(5) . . . . ? O4 C41 C46 C45 179.5(4) . . . . ? O4 C40 C34 C35 76.7(6) . . . . ? O4 C40 C34 C39 -109.6(5) . . . . ? C3 C2 C1 C7 -174.8(4) . . . . ? C3 C2 C1 C6 2.9(7) . . . . ? C3 C2 C30 C31 -82.2(6) . . . . ? C3 C4 C32 C33 90.8(6) . . . . ? C36 C35 C61 C62 85.4(6) . . . . ? C36 C35 C34 C39 -5.9(7) . . . . ? C36 C35 C34 C40 167.7(4) . . . . ? C36 C37 C63 C64 -93.8(6) . . . . ? C36 C37 C38 C54 -177.3(4) . . . . ? C36 C37 C38 C39 -2.7(7) . . . . ? C48 O5 C47 C36 171.7(4) . . . . ? C48 C49 C50 C51 0.0(8) . . . . ? C25 C26 C27 C22 0.2(8) . . . . ? C51 C52 C53 C48 -0.4(8) . . . . ? C47 O5 C48 C49 2.3(7) . . . . ? C47 O5 C48 C53 -178.3(4) . . . . ? C47 C36 C35 C61 4.9(7) . . . . ? C47 C36 C35 C34 -177.9(4) . . . . ? C47 C36 C37 C63 1.2(7) . . . . ? C47 C36 C37 C38 -177.8(4) . . . . ? C54 O6 C55 C60 -8.4(7) . . . . ? C54 O6 C55 C56 170.7(4) . . . . ? C49 C48 C53 C52 -0.7(8) . . . . ? C35 C36 C47 O5 90.9(5) . . . . ? C35 C36 C37 C63 -173.8(4) . . . . ? C35 C36 C37 C38 7.2(7) . . . . ? C2 C3 C4 C5 -2.1(7) . . . . ? C2 C3 C4 C32 178.8(4) . . . . ? C2 C3 C14 O2 -87.3(5) . . . . ? C2 C1 C6 C5 -0.2(7) . . . . ? C2 C1 C6 C28 178.0(4) . . . . ? C37 C36 C47 O5 -84.2(5) . . . . ? C37 C36 C35 C61 179.9(4) . . . . ? C37 C36 C35 C34 -2.9(7) . . . . ? C5 C4 C32 C33 -88.3(6) . . . . ? C18 C19 C20 C15 0.1(7) . . . . ? C18 C17 C16 C15 0.6(7) . . . . ? C4 C3 C2 C1 -1.7(7) . . . . ? C4 C3 C2 C30 177.1(4) . . . . ? C4 C3 C14 O2 86.9(5) . . . . ? C4 C5 C21 O3 -92.2(5) . . . . ? C4 C5 C6 C28 178.0(4) . . . . ? C4 C5 C6 C1 -3.8(7) . . . . ? C41 O4 C40 C34 -172.7(4) . . . . ? C41 C42 C43 C44 -0.2(8) . . . . ? C41 C46 C45 C44 -0.7(8) . . . . ? C55 O6 C54 C38 -178.7(4) . . . . ? C14 O2 C15 C20 179.6(4) . . . . ? C14 O2 C15 C16 0.4(7) . . . . ? C14 C3 C2 C1 172.4(4) . . . . ? C14 C3 C2 C30 -8.8(6) . . . . ? C14 C3 C4 C5 -176.3(4) . . . . ? C14 C3 C4 C32 4.6(7) . . . . ? C52 C51 C50 C49 -1.1(8) . . . . ? C15 O2 C14 C3 -177.9(4) . . . . ? C19 C18 C17 C16 0.8(7) . . . . ? C21 O3 C22 C23 15.3(7) . . . . ? C21 O3 C22 C27 -163.3(4) . . . . ? C21 C5 C4 C3 -176.7(4) . . . . ? C21 C5 C4 C32 2.5(7) . . . . ? C21 C5 C6 C28 -0.4(7) . . . . ? C21 C5 C6 C1 177.8(4) . . . . ? C23 C22 C27 C26 0.0(8) . . . . ? C63 C37 C38 C54 3.7(7) . . . . ? C63 C37 C38 C39 178.3(4) . . . . ? C20 C15 C16 C17 -1.6(7) . . . . ? C22 O3 C21 C5 177.4(4) . . . . ? C22 C23 C24 C25 -0.5(9) . . . . ? C13 C8 C9 C10 -1.0(8) . . . . ? C50 C51 C52 C53 1.3(7) . . . . ? C61 C35 C34 C39 171.3(4) . . . . ? C61 C35 C34 C40 -15.1(7) . . . . ? C17 C18 C19 C20 -1.2(7) . . . . ? C60 C55 C56 C57 -0.9(8) . . . . ? C60 C59 C58 I6 177.4(4) . . . . ? C60 C59 C58 C57 -1.1(8) . . . . ? C1 C2 C30 C31 96.5(5) . . . . ? C42 C41 C46 C45 0.0(8) . . . . ? C27 C26 C25 I3 179.7(4) . . . . ? C27 C26 C25 C24 -0.6(8) . . . . ? C46 C41 C42 C43 0.4(8) . . . . ? C16 C15 C20 C19 1.3(7) . . . . ? C58 C57 C56 C55 -0.2(8) . . . . ? C58 C59 C60 C55 0.0(8) . . . . ? C38 C37 C63 C64 85.2(6) . . . . ? C38 C39 C34 C35 10.3(7) . . . . ? C38 C39 C34 C40 -163.2(4) . . . . ? C38 C39 C65 C66 84.0(6) . . . . ? C40 O4 C41 C42 -13.7(7) . . . . ? C40 O4 C41 C46 166.9(4) . . . . ? C30 C2 C1 C7 6.4(7) . . . . ? C30 C2 C1 C6 -175.9(4) . . . . ? C34 C35 C61 C62 -91.7(6) . . . . ? C34 C39 C38 C54 168.5(4) . . . . ? C34 C39 C38 C37 -6.0(7) . . . . ? C34 C39 C65 C66 -96.6(6) . . . . ? C9 C8 C13 C12 0.1(8) . . . . ? C12 C11 C10 C9 -0.1(8) . . . . ? C6 C5 C4 C3 4.9(7) . . . . ? C6 C5 C4 C32 -176.0(4) . . . . ? C6 C5 C21 O3 86.2(5) . . . . ? C43 C44 C45 C46 0.9(8) . . . . ? C10 C11 C12 C13 -0.7(8) . . . . ? C24 C23 C22 O3 -178.5(5) . . . . ? C24 C23 C22 C27 0.1(8) . . . . ? C53 C48 C49 C50 0.9(7) . . . . ? C56 C55 C60 C59 1.0(8) . . . . ? C56 C57 C58 I6 -177.3(4) . . . . ? C56 C57 C58 C59 1.2(8) . . . . ? C65 C39 C38 C54 -12.1(7) . . . . ? C65 C39 C38 C37 173.4(4) . . . . ? C65 C39 C34 C35 -169.0(4) . . . . ? C65 C39 C34 C40 17.4(7) . . . . ? C45 C44 C43 C42 -0.5(8) . . . . ? C29 C28 C6 C5 97.6(5) . . . . ? C29 C28 C6 C1 -80.5(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962418' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-gf-190K _audit_creation_date 2013-12-25 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-gf, 190 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 I3 O3' _chemical_formula_sum 'C33 H33 I3 O3' _chemical_formula_weight 858.29 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.5482(7) _cell_length_b 13.3514(5) _cell_length_c 26.3226(8) _cell_angle_alpha 90.00 _cell_angle_beta 108.848(4) _cell_angle_gamma 90.00 _cell_volume 6501.7(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4078 _cell_measurement_temperature 190(2) _cell_measurement_theta_max 29.1237 _cell_measurement_theta_min 3.6296 _exptl_absorpt_coefficient_mu 2.915 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 3312 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.07 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_unetI/netI 0.0797 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 27189 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.19 _diffrn_reflns_theta_min 3.64 _diffrn_ambient_temperature 190(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.835 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0346664000 _diffrn_orient_matrix_UB_12 0.0215516000 _diffrn_orient_matrix_UB_13 -0.0120011000 _diffrn_orient_matrix_UB_21 -0.0090329000 _diffrn_orient_matrix_UB_22 -0.0109232000 _diffrn_orient_matrix_UB_23 0.0234249000 _diffrn_orient_matrix_UB_31 0.0136812000 _diffrn_orient_matrix_UB_32 0.0473072000 _diffrn_orient_matrix_UB_33 0.0108631000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 8901 _reflns_number_total 14718 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 1.990 _refine_diff_density_min -1.668 _refine_diff_density_rms 0.127 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 14718 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1101 _refine_ls_R_factor_gt 0.0542 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0930 _refine_ls_wR_factor_ref 0.1150 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C47(H47A,H47B), C54(H54A,H54B), C14(H14A,H14B), C21(H21A,H21B), C63(H63A,H63B), C28(H28A,H28B), C61(H61A,H61B), C40(H40A,H40B), C30(H30A,H30B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C26(H26), C49(H49), C52(H52), C19(H19), C57(H57), C23(H23), C20(H20), C59(H59), C13(H13), C50(H50), C17(H17), C60(H60), C42(H42), C27(H27), C46(H46), C16(H16), C9(H9), C12(H12), C43(H43), C10(H10), C24(H24), C53(H53), C56(H56), C45(H45) 2.c Idealised Me refined as rotating group: C62(H62A,H62B,H62C), C64(H64A,H64B,H64C), C33(H33A,H33B,H33C), C31(H31A,H31B, H31C), C66(H66A,H66B,H66C), C29(H29A,H29B,H29C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I5 I 0.54153(2) 0.69208(3) 0.286627(16) 0.04666(13) Uani 1 1 d . . . I2 I -0.03421(2) 0.30512(3) 0.726473(16) 0.04793(13) Uani 1 1 d . . . I6 I 0.32723(2) 0.45230(3) 0.774792(16) 0.04989(13) Uani 1 1 d . . . I3 I 0.17034(2) 0.56405(4) 0.212420(16) 0.05285(14) Uani 1 1 d . . . I4 I -0.02007(2) 1.54119(3) 0.40946(2) 0.06320(16) Uani 1 1 d . . . I1 I 0.52867(2) -0.52252(3) 0.59447(2) 0.06970(18) Uani 1 1 d . . . O2 O 0.17664(18) 0.1871(3) 0.60284(14) 0.0327(9) Uani 1 1 d . . . O3 O 0.23626(18) 0.2773(3) 0.40872(15) 0.0358(9) Uani 1 1 d . . . O1 O 0.40945(18) -0.0864(3) 0.56904(14) 0.0323(9) Uani 1 1 d . . . O6 O 0.23619(19) 0.7176(3) 0.56885(14) 0.0363(10) Uani 1 1 d . . . O5 O 0.31350(18) 0.8224(3) 0.39345(14) 0.0324(9) Uani 1 1 d . . . C7 C 0.3410(3) -0.0642(4) 0.5281(2) 0.0276(12) Uani 1 1 d . . . H7A H 0.3024 -0.1073 0.5330 0.033 Uiso 1 1 calc . . R H7B H 0.3446 -0.0774 0.4920 0.033 Uiso 1 1 calc . . R C26 C 0.1385(3) 0.4155(5) 0.2894(2) 0.0402(15) Uani 1 1 d . . . H26 H 0.0898 0.4237 0.2669 0.048 Uiso 1 1 calc . . R C8 C 0.4322(3) -0.1833(4) 0.5717(2) 0.0256(12) Uani 1 1 d . . . O4 O 0.06075(18) 1.0884(3) 0.41777(14) 0.0329(9) Uani 1 1 d . . . C3 C 0.2821(3) 0.1773(4) 0.5792(2) 0.0255(12) Uani 1 1 d . . . C36 C 0.2005(3) 0.8274(4) 0.4092(2) 0.0270(12) Uani 1 1 d . . . C48 C 0.3603(3) 0.7931(4) 0.3668(2) 0.0267(12) Uani 1 1 d . . . C25 C 0.1935(3) 0.4664(4) 0.2790(2) 0.0360(14) Uani 1 1 d . . . C51 C 0.4637(3) 0.7399(4) 0.3213(2) 0.0311(13) Uani 1 1 d . . . C47 C 0.2372(2) 0.8000(4) 0.3682(2) 0.0299(13) Uani 1 1 d . . . H47A H 0.2303 0.7281 0.3589 0.036 Uiso 1 1 calc . . R H47B H 0.2170 0.8400 0.3350 0.036 Uiso 1 1 calc . . R C54 C 0.1662(3) 0.7041(4) 0.5284(2) 0.0326(13) Uani 1 1 d . . . H54A H 0.1270 0.7174 0.5436 0.039 Uiso 1 1 calc . . R H54B H 0.1610 0.6348 0.5142 0.039 Uiso 1 1 calc . . R C49 C 0.3397(3) 0.7471(4) 0.3172(2) 0.0298(13) Uani 1 1 d . . . H49 H 0.2901 0.7339 0.2987 0.036 Uiso 1 1 calc . . R C35 C 0.1726(3) 0.9239(4) 0.4096(2) 0.0240(11) Uani 1 1 d . . . C2 C 0.3044(2) 0.0780(4) 0.5775(2) 0.0234(11) Uani 1 1 d . . . C37 C 0.2001(3) 0.7558(4) 0.4481(2) 0.0264(12) Uani 1 1 d . . . C5 C 0.3028(3) 0.2120(4) 0.4949(2) 0.0276(12) Uani 1 1 d . . . C18 C 0.0399(3) 0.2596(4) 0.6882(2) 0.0309(13) Uani 1 1 d . . . C4 C 0.2798(3) 0.2446(4) 0.5375(2) 0.0278(12) Uani 1 1 d . . . C41 C 0.0462(3) 1.1883(4) 0.4186(2) 0.0276(12) Uani 1 1 d . . . C55 C 0.2526(3) 0.6568(4) 0.6131(2) 0.0291(13) Uani 1 1 d . . . C14 C 0.2531(3) 0.2099(4) 0.6231(2) 0.0321(13) Uani 1 1 d . . . H14A H 0.2769 0.1726 0.6567 0.038 Uiso 1 1 calc . . R H14B H 0.2609 0.2825 0.6303 0.038 Uiso 1 1 calc . . R C52 C 0.4843(3) 0.7864(4) 0.3703(2) 0.0375(14) Uani 1 1 d . . . H52 H 0.5339 0.8005 0.3883 0.045 Uiso 1 1 calc . . R C15 C 0.1350(3) 0.2127(4) 0.6338(2) 0.0260(12) Uani 1 1 d . . . C19 C 0.0145(3) 0.2133(4) 0.6391(2) 0.0296(13) Uani 1 1 d . . . H19 H -0.0354 0.1981 0.6238 0.036 Uiso 1 1 calc . . R C21 C 0.3042(3) 0.2842(4) 0.4512(2) 0.0328(13) Uani 1 1 d . . . H21A H 0.3117 0.3533 0.4655 0.039 Uiso 1 1 calc . . R H21B H 0.3443 0.2671 0.4375 0.039 Uiso 1 1 calc . . R C57 C 0.3453(3) 0.6008(5) 0.6925(2) 0.0389(15) Uani 1 1 d . . . H57 H 0.3940 0.6028 0.7155 0.047 Uiso 1 1 calc . . R C23 C 0.2804(3) 0.3921(5) 0.3550(2) 0.0470(17) Uani 1 1 d . . . H23 H 0.3290 0.3841 0.3775 0.056 Uiso 1 1 calc . . R C11 C 0.4888(3) -0.3748(4) 0.5847(2) 0.0369(14) Uani 1 1 d . . . C63 C 0.2370(3) 0.6553(4) 0.4501(2) 0.0306(13) Uani 1 1 d . . . H63A H 0.2582 0.6343 0.4880 0.037 Uiso 1 1 calc . . R H63B H 0.2769 0.6628 0.4349 0.037 Uiso 1 1 calc . . R C20 C 0.0623(3) 0.1891(4) 0.6121(2) 0.0303(13) Uani 1 1 d . . . H20 H 0.0452 0.1561 0.5784 0.036 Uiso 1 1 calc . . R C39 C 0.1310(3) 0.8721(4) 0.4839(2) 0.0253(12) Uani 1 1 d . . . C22 C 0.2253(3) 0.3399(4) 0.3658(2) 0.0328(13) Uani 1 1 d . . . C59 C 0.2262(3) 0.5333(5) 0.6700(2) 0.0426(16) Uani 1 1 d . . . H59 H 0.1930 0.4886 0.6776 0.051 Uiso 1 1 calc . . R C13 C 0.4059(3) -0.2532(4) 0.5321(2) 0.0356(14) Uani 1 1 d . . . H13 H 0.3684 -0.2357 0.5001 0.043 Uiso 1 1 calc . . R C50 C 0.3924(3) 0.7202(4) 0.2946(2) 0.0313(13) Uani 1 1 d . . . H50 H 0.3788 0.6882 0.2606 0.038 Uiso 1 1 calc . . R C28 C 0.3449(3) 0.0776(4) 0.4442(2) 0.0352(14) Uani 1 1 d . . . H28A H 0.3259 0.0094 0.4333 0.042 Uiso 1 1 calc . . R H28B H 0.3240 0.1231 0.4134 0.042 Uiso 1 1 calc . . R C61 C 0.1738(3) 1.0008(4) 0.3681(2) 0.0354(14) Uani 1 1 d . . . H61A H 0.2181 0.9917 0.3581 0.042 Uiso 1 1 calc . . R H61B H 0.1754 1.0686 0.3836 0.042 Uiso 1 1 calc . . R C17 C 0.1121(3) 0.2819(4) 0.7108(2) 0.0339(14) Uani 1 1 d . . . H17 H 0.1291 0.3140 0.7448 0.041 Uiso 1 1 calc . . R C60 C 0.2040(3) 0.5925(4) 0.6245(2) 0.0389(15) Uani 1 1 d . . . H60 H 0.1555 0.5891 0.6012 0.047 Uiso 1 1 calc . . R C44 C 0.0068(3) 1.3884(4) 0.4136(3) 0.0368(14) Uani 1 1 d . . . C1 C 0.3233(2) 0.0440(4) 0.5329(2) 0.0255(12) Uani 1 1 d . . . C42 C 0.0784(3) 1.2516(4) 0.4618(2) 0.0337(14) Uani 1 1 d . . . H42 H 0.1135 1.2262 0.4931 0.040 Uiso 1 1 calc . . R C27 C 0.1553(3) 0.3521(4) 0.3332(2) 0.0355(14) Uani 1 1 d . . . H27 H 0.1177 0.3164 0.3409 0.043 Uiso 1 1 calc . . R C46 C -0.0056(3) 1.2265(4) 0.3730(2) 0.0347(14) Uani 1 1 d . . . H46 H -0.0280 1.1838 0.3435 0.042 Uiso 1 1 calc . . R C16 C 0.1602(3) 0.2571(4) 0.6836(2) 0.0293(13) Uani 1 1 d . . . H16 H 0.2103 0.2708 0.6993 0.035 Uiso 1 1 calc . . R C58 C 0.2963(3) 0.5390(4) 0.7044(2) 0.0339(14) Uani 1 1 d . . . C38 C 0.1635(3) 0.7785(4) 0.4844(2) 0.0242(12) Uani 1 1 d . . . C40 C 0.1244(3) 1.0545(4) 0.4585(2) 0.0325(13) Uani 1 1 d . . . H40A H 0.1177 1.0609 0.4941 0.039 Uiso 1 1 calc . . R H40B H 0.1659 1.0971 0.4585 0.039 Uiso 1 1 calc . . R C30 C 0.3099(3) 0.0075(4) 0.6239(2) 0.0328(13) Uani 1 1 d . . . H30A H 0.2688 0.0204 0.6373 0.039 Uiso 1 1 calc . . R H30B H 0.3056 -0.0623 0.6105 0.039 Uiso 1 1 calc . . R C34 C 0.1407(3) 0.9466(4) 0.4493(2) 0.0268(12) Uani 1 1 d . . . C9 C 0.4875(3) -0.2101(4) 0.6186(2) 0.0372(14) Uani 1 1 d . . . H9 H 0.5057 -0.1623 0.6464 0.045 Uiso 1 1 calc . . R C32 C 0.2536(3) 0.3510(4) 0.5384(2) 0.0356(14) Uani 1 1 d . . . H32A H 0.2176 0.3525 0.5575 0.043 Uiso 1 1 calc . . R H32B H 0.2292 0.3735 0.5010 0.043 Uiso 1 1 calc . . R C62 C 0.1077(3) 0.9923(5) 0.3179(2) 0.0496(17) Uani 1 1 d . . . H62A H 0.0639 1.0061 0.3272 0.074 Uiso 1 1 calc . . GR H62B H 0.1050 0.9245 0.3031 0.074 Uiso 1 1 calc . . GR H62C H 0.1116 1.0409 0.2910 0.074 Uiso 1 1 calc . . GR C12 C 0.4345(3) -0.3504(4) 0.5388(2) 0.0400(15) Uani 1 1 d . . . H12 H 0.4162 -0.3991 0.5115 0.048 Uiso 1 1 calc . . R C6 C 0.3223(2) 0.1118(4) 0.4915(2) 0.0264(12) Uani 1 1 d . . . C43 C 0.0588(3) 1.3522(4) 0.4587(2) 0.0377(15) Uani 1 1 d . . . H43 H 0.0814 1.3960 0.4878 0.045 Uiso 1 1 calc . . R C10 C 0.5154(3) -0.3053(5) 0.6245(2) 0.0405(15) Uani 1 1 d . . . H10 H 0.5531 -0.3231 0.6563 0.049 Uiso 1 1 calc . . R C24 C 0.2640(3) 0.4558(5) 0.3112(2) 0.0471(17) Uani 1 1 d . . . H24 H 0.3014 0.4920 0.3036 0.057 Uiso 1 1 calc . . R C64 C 0.1857(3) 0.5731(4) 0.4191(2) 0.0463(16) Uani 1 1 d . . . H64A H 0.1457 0.5657 0.4335 0.069 Uiso 1 1 calc . . GR H64B H 0.2121 0.5097 0.4228 0.069 Uiso 1 1 calc . . GR H64C H 0.1666 0.5914 0.3810 0.069 Uiso 1 1 calc . . GR C33 C 0.3151(3) 0.4238(4) 0.5657(2) 0.0475(17) Uani 1 1 d . . . H33A H 0.3523 0.4198 0.5482 0.071 Uiso 1 1 calc . . GR H33B H 0.3363 0.4059 0.6037 0.071 Uiso 1 1 calc . . GR H33C H 0.2961 0.4922 0.5627 0.071 Uiso 1 1 calc . . GR C53 C 0.4326(3) 0.8129(4) 0.3934(2) 0.0346(14) Uani 1 1 d . . . H53 H 0.4467 0.8447 0.4276 0.042 Uiso 1 1 calc . . R C56 C 0.3233(3) 0.6602(4) 0.6469(2) 0.0374(14) Uani 1 1 d . . . H56 H 0.3570 0.7034 0.6389 0.045 Uiso 1 1 calc . . R C65 C 0.0845(3) 0.8930(4) 0.5194(2) 0.0309(13) Uani 1 1 d . . . H65A H 0.0491 0.9458 0.5020 0.037 Uiso 1 1 calc . . R H65B H 0.0569 0.8316 0.5209 0.037 Uiso 1 1 calc . . R C45 C -0.0241(3) 1.3262(5) 0.3709(3) 0.0426(16) Uani 1 1 d . . . H45 H -0.0588 1.3523 0.3395 0.051 Uiso 1 1 calc . . R C31 C 0.3797(3) 0.0179(5) 0.6701(2) 0.0482(17) Uani 1 1 d . . . H31A H 0.4207 0.0041 0.6574 0.072 Uiso 1 1 calc . . GR H31B H 0.3800 -0.0299 0.6984 0.072 Uiso 1 1 calc . . GR H31C H 0.3837 0.0862 0.6844 0.072 Uiso 1 1 calc . . GR C66 C 0.1249(3) 0.9256(5) 0.5763(2) 0.0422(15) Uani 1 1 d . . . H66A H 0.1586 0.8727 0.5947 0.063 Uiso 1 1 calc . . GR H66B H 0.0904 0.9380 0.5955 0.063 Uiso 1 1 calc . . GR H66C H 0.1519 0.9872 0.5756 0.063 Uiso 1 1 calc . . GR C29 C 0.4264(3) 0.0769(5) 0.4588(3) 0.0516(18) Uani 1 1 d . . . H29A H 0.4398 0.0503 0.4286 0.077 Uiso 1 1 calc . . GR H29B H 0.4473 0.0346 0.4904 0.077 Uiso 1 1 calc . . GR H29C H 0.4449 0.1454 0.4667 0.077 Uiso 1 1 calc . . GR 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 I5 0.0415(2) 0.0593(3) 0.0466(3) -0.0088(2) 0.02456(19) 0.0034(2) I2 0.0462(2) 0.0637(3) 0.0405(2) -0.0079(2) 0.02315(19) 0.0048(2) I6 0.0577(3) 0.0584(3) 0.0315(2) 0.0147(2) 0.01152(19) 0.0155(2) I3 0.0609(3) 0.0632(3) 0.0360(2) 0.0158(2) 0.0178(2) 0.0203(2) I4 0.0412(2) 0.0251(2) 0.1138(4) 0.0173(3) 0.0121(2) 0.00752(19) I1 0.0466(3) 0.0292(2) 0.1225(5) 0.0200(3) 0.0125(3) 0.0118(2) O2 0.0274(19) 0.041(2) 0.031(2) -0.0144(19) 0.0110(16) -0.0030(17) O3 0.030(2) 0.036(2) 0.037(2) 0.012(2) 0.0049(17) -0.0038(18) O1 0.031(2) 0.024(2) 0.038(2) -0.0006(18) 0.0051(17) 0.0040(16) O6 0.036(2) 0.035(2) 0.032(2) 0.0118(19) 0.0031(17) -0.0097(18) O5 0.032(2) 0.037(2) 0.031(2) -0.0089(19) 0.0132(16) 0.0021(18) C7 0.026(3) 0.023(3) 0.029(3) 0.000(3) 0.002(2) 0.004(2) C26 0.033(3) 0.045(4) 0.037(3) -0.007(3) 0.004(3) 0.002(3) C8 0.025(3) 0.018(3) 0.033(3) 0.002(3) 0.008(2) 0.000(2) O4 0.031(2) 0.022(2) 0.041(2) -0.0009(19) 0.0050(17) 0.0043(16) C3 0.024(3) 0.022(3) 0.029(3) 0.002(3) 0.006(2) 0.002(2) C36 0.021(3) 0.032(3) 0.027(3) 0.001(3) 0.007(2) 0.003(2) C48 0.032(3) 0.022(3) 0.029(3) 0.003(3) 0.013(2) 0.005(2) C25 0.042(3) 0.039(4) 0.027(3) -0.004(3) 0.011(3) 0.008(3) C51 0.036(3) 0.027(3) 0.036(3) 0.003(3) 0.021(3) 0.004(3) C47 0.020(3) 0.034(3) 0.031(3) -0.003(3) 0.003(2) 0.000(2) C54 0.033(3) 0.031(3) 0.033(3) 0.003(3) 0.009(2) -0.003(3) C49 0.030(3) 0.028(3) 0.032(3) 0.002(3) 0.009(2) 0.002(2) C35 0.025(3) 0.020(3) 0.024(3) 0.002(2) 0.006(2) -0.001(2) C2 0.019(2) 0.023(3) 0.027(3) 0.002(2) 0.005(2) -0.001(2) C37 0.026(3) 0.021(3) 0.030(3) 0.000(3) 0.005(2) 0.005(2) C5 0.023(3) 0.020(3) 0.037(3) 0.005(3) 0.006(2) 0.000(2) C18 0.039(3) 0.028(3) 0.028(3) 0.003(3) 0.014(2) 0.002(3) C4 0.024(3) 0.022(3) 0.035(3) -0.002(3) 0.006(2) 0.002(2) C41 0.025(3) 0.022(3) 0.038(3) 0.001(3) 0.014(2) 0.005(2) C55 0.029(3) 0.026(3) 0.033(3) 0.004(3) 0.011(2) 0.001(2) C14 0.027(3) 0.037(3) 0.029(3) -0.007(3) 0.006(2) 0.000(3) C52 0.040(3) 0.035(4) 0.039(4) -0.007(3) 0.014(3) 0.000(3) C15 0.028(3) 0.025(3) 0.025(3) -0.002(3) 0.008(2) 0.003(2) C19 0.027(3) 0.029(3) 0.035(3) -0.003(3) 0.012(2) -0.002(2) C21 0.040(3) 0.026(3) 0.034(3) 0.005(3) 0.013(3) -0.001(3) C57 0.035(3) 0.045(4) 0.030(3) -0.009(3) 0.001(3) 0.001(3) C23 0.034(3) 0.053(4) 0.051(4) 0.024(4) 0.011(3) 0.010(3) C11 0.040(3) 0.017(3) 0.052(4) 0.007(3) 0.011(3) 0.007(3) C63 0.035(3) 0.022(3) 0.033(3) -0.002(3) 0.009(2) 0.003(2) C20 0.035(3) 0.028(3) 0.028(3) -0.009(3) 0.010(2) -0.002(3) C39 0.024(3) 0.025(3) 0.027(3) -0.004(3) 0.009(2) -0.002(2) C22 0.037(3) 0.029(3) 0.030(3) 0.003(3) 0.008(3) 0.004(3) C59 0.032(3) 0.048(4) 0.047(4) 0.017(3) 0.011(3) 0.005(3) C13 0.033(3) 0.029(3) 0.040(3) 0.000(3) 0.004(3) 0.000(3) C50 0.038(3) 0.029(3) 0.026(3) -0.007(3) 0.009(2) 0.005(3) C28 0.033(3) 0.036(3) 0.037(3) 0.003(3) 0.012(3) 0.000(3) C61 0.034(3) 0.033(3) 0.043(4) 0.007(3) 0.017(3) 0.001(3) C17 0.037(3) 0.035(3) 0.024(3) -0.005(3) 0.003(2) -0.001(3) C60 0.029(3) 0.045(4) 0.038(3) 0.013(3) 0.004(3) 0.001(3) C44 0.035(3) 0.020(3) 0.057(4) 0.003(3) 0.017(3) 0.002(3) C1 0.021(2) 0.023(3) 0.031(3) -0.002(3) 0.006(2) 0.001(2) C42 0.030(3) 0.025(3) 0.040(3) 0.006(3) 0.004(3) 0.006(2) C27 0.031(3) 0.037(4) 0.035(3) -0.002(3) 0.006(3) -0.003(3) C46 0.035(3) 0.038(4) 0.031(3) 0.002(3) 0.011(3) 0.005(3) C16 0.027(3) 0.031(3) 0.027(3) 0.002(3) 0.004(2) 0.005(2) C58 0.042(3) 0.033(3) 0.029(3) 0.006(3) 0.014(3) 0.012(3) C38 0.027(3) 0.020(3) 0.025(3) 0.003(2) 0.008(2) -0.003(2) C40 0.032(3) 0.028(3) 0.036(3) 0.003(3) 0.008(2) 0.003(3) C30 0.039(3) 0.027(3) 0.034(3) -0.001(3) 0.015(3) 0.000(3) C34 0.027(3) 0.017(3) 0.036(3) 0.001(3) 0.010(2) 0.007(2) C9 0.039(3) 0.039(4) 0.031(3) 0.002(3) 0.007(3) 0.002(3) C32 0.037(3) 0.028(3) 0.039(3) 0.002(3) 0.008(3) 0.006(3) C62 0.054(4) 0.052(4) 0.042(4) 0.020(3) 0.016(3) 0.008(3) C12 0.042(3) 0.021(3) 0.050(4) 0.001(3) 0.005(3) 0.001(3) C6 0.021(3) 0.031(3) 0.026(3) 0.002(3) 0.007(2) 0.004(2) C43 0.032(3) 0.027(3) 0.048(4) -0.002(3) 0.004(3) 0.005(3) C10 0.032(3) 0.046(4) 0.040(4) 0.015(3) 0.006(3) 0.008(3) C24 0.040(3) 0.053(4) 0.052(4) 0.024(4) 0.021(3) 0.005(3) C64 0.053(4) 0.027(3) 0.055(4) -0.010(3) 0.011(3) 0.004(3) C33 0.057(4) 0.024(3) 0.054(4) -0.006(3) 0.007(3) -0.003(3) C53 0.035(3) 0.034(3) 0.037(3) -0.008(3) 0.015(3) -0.002(3) C56 0.039(3) 0.036(3) 0.034(3) -0.004(3) 0.007(3) -0.008(3) C65 0.031(3) 0.032(3) 0.031(3) -0.001(3) 0.011(2) 0.002(3) C45 0.038(3) 0.039(4) 0.050(4) 0.020(3) 0.014(3) 0.016(3) C31 0.050(4) 0.052(4) 0.036(4) 0.013(3) 0.005(3) 0.008(3) C66 0.042(3) 0.051(4) 0.035(3) -0.011(3) 0.014(3) -0.005(3) C29 0.047(4) 0.060(5) 0.055(4) 0.008(4) 0.028(3) 0.004(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 I5 C51 2.110(5) . ? I2 C18 2.103(5) . ? I6 C58 2.102(5) . ? I3 C25 2.111(6) . ? I4 C44 2.101(5) . ? I1 C11 2.105(5) . ? O2 C14 1.447(6) . ? O2 C15 1.368(6) . ? O3 C21 1.436(6) . ? O3 C22 1.366(6) . ? O1 C7 1.452(5) . ? O1 C8 1.362(6) . ? O6 C54 1.448(6) . ? O6 C55 1.371(6) . ? O5 C48 1.378(6) . ? O5 C47 1.454(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C1 1.500(7) . ? C26 H26 0.9500 . ? C26 C25 1.373(8) . ? C26 C27 1.383(8) . ? C8 C13 1.370(7) . ? C8 C9 1.398(7) . ? O4 C41 1.366(6) . ? O4 C40 1.429(6) . ? C3 C2 1.401(7) . ? C3 C4 1.407(7) . ? C3 C14 1.509(7) . ? C36 C47 1.520(7) . ? C36 C35 1.401(7) . ? C36 C37 1.404(7) . ? C48 C49 1.378(7) . ? C48 C53 1.386(7) . ? C25 C24 1.373(7) . ? C51 C52 1.369(7) . ? C51 C50 1.369(7) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C54 C38 1.512(7) . ? C49 H49 0.9500 . ? C49 C50 1.393(7) . ? C35 C61 1.506(7) . ? C35 C34 1.411(7) . ? C2 C1 1.416(7) . ? C2 C30 1.518(7) . ? C37 C63 1.516(7) . ? C37 C38 1.400(7) . ? C5 C4 1.405(7) . ? C5 C21 1.507(7) . ? C5 C6 1.402(7) . ? C18 C19 1.373(7) . ? C18 C17 1.375(7) . ? C4 C32 1.513(7) . ? C41 C42 1.392(7) . ? C41 C46 1.392(7) . ? C55 C60 1.383(7) . ? C55 C56 1.382(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C52 H52 0.9500 . ? C52 C53 1.383(7) . ? C15 C20 1.387(7) . ? C15 C16 1.375(7) . ? C19 H19 0.9500 . ? C19 C20 1.383(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C57 H57 0.9500 . ? C57 C58 1.374(8) . ? C57 C56 1.385(8) . ? C23 H23 0.9500 . ? C23 C22 1.387(7) . ? C23 C24 1.385(8) . ? C11 C12 1.365(7) . ? C11 C10 1.371(8) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C63 C64 1.531(7) . ? C20 H20 0.9500 . ? C39 C38 1.400(7) . ? C39 C34 1.403(7) . ? C39 C65 1.524(7) . ? C22 C27 1.370(7) . ? C59 H59 0.9500 . ? C59 C60 1.382(7) . ? C59 C58 1.378(7) . ? C13 H13 0.9500 . ? C13 C12 1.402(7) . ? C50 H50 0.9500 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C6 1.519(7) . ? C28 C29 1.514(7) . ? C61 H61A 0.9900 . ? C61 H61B 0.9900 . ? C61 C62 1.525(7) . ? C17 H17 0.9500 . ? C17 C16 1.395(7) . ? C60 H60 0.9500 . ? C44 C43 1.377(7) . ? C44 C45 1.371(8) . ? C1 C6 1.412(7) . ? C42 H42 0.9500 . ? C42 C43 1.392(7) . ? C27 H27 0.9500 . ? C46 H46 0.9500 . ? C46 C45 1.377(8) . ? C16 H16 0.9500 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C40 C34 1.511(7) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 C31 1.513(7) . ? C9 H9 0.9500 . ? C9 C10 1.372(8) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C33 1.533(7) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C12 H12 0.9500 . ? C43 H43 0.9500 . ? C10 H10 0.9500 . ? C24 H24 0.9500 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C53 H53 0.9500 . ? C56 H56 0.9500 . ? C65 H65A 0.9900 . ? C65 H65B 0.9900 . ? C65 C66 1.515(7) . ? C45 H45 0.9500 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O2 C14 117.9(4) . . ? C22 O3 C21 117.6(4) . . ? C8 O1 C7 116.1(4) . . ? C55 O6 C54 117.3(4) . . ? C48 O5 C47 117.4(4) . . ? O1 C7 H7A 110.0 . . ? O1 C7 H7B 110.0 . . ? O1 C7 C1 108.5(4) . . ? H7A C7 H7B 108.4 . . ? C1 C7 H7A 110.0 . . ? C1 C7 H7B 110.0 . . ? C25 C26 H26 120.7 . . ? C25 C26 C27 118.7(5) . . ? C27 C26 H26 120.7 . . ? O1 C8 C13 124.8(5) . . ? O1 C8 C9 115.8(5) . . ? C13 C8 C9 119.4(5) . . ? C41 O4 C40 115.6(4) . . ? C2 C3 C4 120.8(5) . . ? C2 C3 C14 119.6(5) . . ? C4 C3 C14 119.3(5) . . ? C35 C36 C47 120.1(5) . . ? C35 C36 C37 121.7(5) . . ? C37 C36 C47 118.0(5) . . ? O5 C48 C49 124.7(5) . . ? O5 C48 C53 115.1(5) . . ? C49 C48 C53 120.2(5) . . ? C26 C25 I3 120.0(4) . . ? C24 C25 I3 118.7(4) . . ? C24 C25 C26 121.3(6) . . ? C52 C51 I5 120.8(4) . . ? C50 C51 I5 118.5(4) . . ? C50 C51 C52 120.7(5) . . ? O5 C47 C36 106.0(4) . . ? O5 C47 H47A 110.5 . . ? O5 C47 H47B 110.5 . . ? C36 C47 H47A 110.5 . . ? C36 C47 H47B 110.5 . . ? H47A C47 H47B 108.7 . . ? O6 C54 H54A 110.6 . . ? O6 C54 H54B 110.6 . . ? O6 C54 C38 105.8(4) . . ? H54A C54 H54B 108.7 . . ? C38 C54 H54A 110.6 . . ? C38 C54 H54B 110.6 . . ? C48 C49 H49 120.4 . . ? C48 C49 C50 119.2(5) . . ? C50 C49 H49 120.4 . . ? C36 C35 C61 121.5(5) . . ? C36 C35 C34 118.1(5) . . ? C34 C35 C61 120.4(5) . . ? C3 C2 C1 119.8(5) . . ? C3 C2 C30 120.3(5) . . ? C1 C2 C30 119.9(5) . . ? C36 C37 C63 120.8(5) . . ? C38 C37 C36 118.4(5) . . ? C38 C37 C63 120.8(5) . . ? C4 C5 C21 120.0(5) . . ? C6 C5 C4 120.7(5) . . ? C6 C5 C21 119.3(5) . . ? C19 C18 I2 119.0(4) . . ? C19 C18 C17 120.9(5) . . ? C17 C18 I2 120.0(4) . . ? C3 C4 C32 120.9(5) . . ? C5 C4 C3 119.1(5) . . ? C5 C4 C32 120.0(5) . . ? O4 C41 C42 124.4(5) . . ? O4 C41 C46 116.1(5) . . ? C42 C41 C46 119.5(5) . . ? O6 C55 C60 124.2(5) . . ? O6 C55 C56 116.1(5) . . ? C56 C55 C60 119.7(5) . . ? O2 C14 C3 104.8(4) . . ? O2 C14 H14A 110.8 . . ? O2 C14 H14B 110.8 . . ? C3 C14 H14A 110.8 . . ? C3 C14 H14B 110.8 . . ? H14A C14 H14B 108.9 . . ? C51 C52 H52 120.1 . . ? C51 C52 C53 119.8(5) . . ? C53 C52 H52 120.1 . . ? O2 C15 C20 115.2(4) . . ? O2 C15 C16 125.2(4) . . ? C16 C15 C20 119.7(5) . . ? C18 C19 H19 120.3 . . ? C18 C19 C20 119.4(5) . . ? C20 C19 H19 120.3 . . ? O3 C21 C5 108.3(4) . . ? O3 C21 H21A 110.0 . . ? O3 C21 H21B 110.0 . . ? C5 C21 H21A 110.0 . . ? C5 C21 H21B 110.0 . . ? H21A C21 H21B 108.4 . . ? C58 C57 H57 120.1 . . ? C58 C57 C56 119.8(5) . . ? C56 C57 H57 120.1 . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C24 C23 C22 119.5(5) . . ? C12 C11 I1 118.9(4) . . ? C12 C11 C10 120.6(5) . . ? C10 C11 I1 120.4(4) . . ? C37 C63 H63A 108.9 . . ? C37 C63 H63B 108.9 . . ? C37 C63 C64 113.2(4) . . ? H63A C63 H63B 107.7 . . ? C64 C63 H63A 108.9 . . ? C64 C63 H63B 108.9 . . ? C15 C20 H20 119.7 . . ? C19 C20 C15 120.5(5) . . ? C19 C20 H20 119.7 . . ? C38 C39 C34 118.9(5) . . ? C38 C39 C65 121.0(5) . . ? C34 C39 C65 120.0(5) . . ? O3 C22 C23 123.5(5) . . ? O3 C22 C27 116.6(5) . . ? C27 C22 C23 119.9(5) . . ? C60 C59 H59 119.8 . . ? C58 C59 H59 119.8 . . ? C58 C59 C60 120.3(5) . . ? C8 C13 H13 120.0 . . ? C8 C13 C12 119.9(5) . . ? C12 C13 H13 120.0 . . ? C51 C50 C49 120.2(5) . . ? C51 C50 H50 119.9 . . ? C49 C50 H50 119.9 . . ? H28A C28 H28B 108.1 . . ? C6 C28 H28A 109.5 . . ? C6 C28 H28B 109.5 . . ? C29 C28 H28A 109.5 . . ? C29 C28 H28B 109.5 . . ? C29 C28 C6 110.8(4) . . ? C35 C61 H61A 109.3 . . ? C35 C61 H61B 109.3 . . ? C35 C61 C62 111.8(4) . . ? H61A C61 H61B 107.9 . . ? C62 C61 H61A 109.3 . . ? C62 C61 H61B 109.3 . . ? C18 C17 H17 120.2 . . ? C18 C17 C16 119.6(5) . . ? C16 C17 H17 120.2 . . ? C55 C60 H60 120.1 . . ? C59 C60 C55 119.8(5) . . ? C59 C60 H60 120.1 . . ? C43 C44 I4 119.2(4) . . ? C45 C44 I4 120.6(4) . . ? C45 C44 C43 120.1(5) . . ? C2 C1 C7 120.6(5) . . ? C6 C1 C7 119.9(5) . . ? C6 C1 C2 119.5(5) . . ? C41 C42 H42 120.2 . . ? C41 C42 C43 119.7(5) . . ? C43 C42 H42 120.2 . . ? C26 C27 H27 119.5 . . ? C22 C27 C26 120.9(5) . . ? C22 C27 H27 119.5 . . ? C41 C46 H46 120.1 . . ? C45 C46 C41 119.9(5) . . ? C45 C46 H46 120.1 . . ? C15 C16 C17 119.9(5) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C57 C58 I6 120.5(4) . . ? C57 C58 C59 120.1(5) . . ? C59 C58 I6 119.4(4) . . ? C37 C38 C54 118.7(5) . . ? C39 C38 C54 119.9(5) . . ? C39 C38 C37 121.1(5) . . ? O4 C40 H40A 109.4 . . ? O4 C40 H40B 109.4 . . ? O4 C40 C34 111.0(4) . . ? H40A C40 H40B 108.0 . . ? C34 C40 H40A 109.4 . . ? C34 C40 H40B 109.4 . . ? C2 C30 H30A 108.9 . . ? C2 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? C31 C30 C2 113.6(4) . . ? C31 C30 H30A 108.9 . . ? C31 C30 H30B 108.9 . . ? C35 C34 C40 119.3(5) . . ? C39 C34 C35 120.8(5) . . ? C39 C34 C40 119.5(5) . . ? C8 C9 H9 119.9 . . ? C10 C9 C8 120.2(5) . . ? C10 C9 H9 119.9 . . ? C4 C32 H32A 109.1 . . ? C4 C32 H32B 109.1 . . ? C4 C32 C33 112.6(4) . . ? H32A C32 H32B 107.8 . . ? C33 C32 H32A 109.1 . . ? C33 C32 H32B 109.1 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C11 C12 C13 119.8(5) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C5 C6 C28 119.8(5) . . ? C5 C6 C1 119.9(5) . . ? C1 C6 C28 120.3(5) . . ? C44 C43 C42 120.1(5) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C11 C10 C9 120.1(5) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C25 C24 C23 119.6(6) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C48 C53 H53 120.1 . . ? C52 C53 C48 119.9(5) . . ? C52 C53 H53 120.1 . . ? C55 C56 C57 120.3(5) . . ? C55 C56 H56 119.8 . . ? C57 C56 H56 119.8 . . ? C39 C65 H65A 108.3 . . ? C39 C65 H65B 108.3 . . ? H65A C65 H65B 107.4 . . ? C66 C65 C39 115.8(4) . . ? C66 C65 H65A 108.3 . . ? C66 C65 H65B 108.3 . . ? C44 C45 C46 120.8(5) . . ? C44 C45 H45 119.6 . . ? C46 C45 H45 119.6 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I5 C51 C52 C53 -177.0(4) . . . . ? I5 C51 C50 C49 177.5(4) . . . . ? I2 C18 C19 C20 175.8(4) . . . . ? I2 C18 C17 C16 -176.0(4) . . . . ? I3 C25 C24 C23 -179.9(5) . . . . ? I4 C44 C43 C42 -178.8(4) . . . . ? I4 C44 C45 C46 178.7(4) . . . . ? I1 C11 C12 C13 178.3(4) . . . . ? I1 C11 C10 C9 -177.8(4) . . . . ? O2 C15 C20 C19 -178.6(5) . . . . ? O2 C15 C16 C17 178.5(5) . . . . ? O3 C22 C27 C26 178.7(5) . . . . ? O1 C7 C1 C2 -69.4(6) . . . . ? O1 C7 C1 C6 113.3(5) . . . . ? O1 C8 C13 C12 178.6(5) . . . . ? O1 C8 C9 C10 -178.3(5) . . . . ? O6 C54 C38 C37 78.3(6) . . . . ? O6 C54 C38 C39 -95.4(5) . . . . ? O6 C55 C60 C59 179.3(5) . . . . ? O6 C55 C56 C57 -179.5(5) . . . . ? O5 C48 C49 C50 -179.5(5) . . . . ? O5 C48 C53 C52 179.9(5) . . . . ? C7 O1 C8 C13 16.7(7) . . . . ? C7 O1 C8 C9 -164.7(5) . . . . ? C7 C1 C6 C5 177.3(4) . . . . ? C7 C1 C6 C28 -4.8(7) . . . . ? C26 C25 C24 C23 0.4(9) . . . . ? C8 O1 C7 C1 177.3(4) . . . . ? C8 C13 C12 C11 -0.5(9) . . . . ? C8 C9 C10 C11 -0.4(9) . . . . ? O4 C41 C42 C43 -179.1(5) . . . . ? O4 C41 C46 C45 179.2(5) . . . . ? O4 C40 C34 C35 77.3(6) . . . . ? O4 C40 C34 C39 -109.2(5) . . . . ? C3 C2 C1 C7 -174.6(4) . . . . ? C3 C2 C1 C6 2.7(7) . . . . ? C3 C2 C30 C31 -82.4(6) . . . . ? C3 C4 C32 C33 91.4(6) . . . . ? C36 C35 C61 C62 86.7(6) . . . . ? C36 C35 C34 C39 -6.1(7) . . . . ? C36 C35 C34 C40 167.2(4) . . . . ? C36 C37 C63 C64 -93.9(6) . . . . ? C36 C37 C38 C54 -176.7(4) . . . . ? C36 C37 C38 C39 -3.1(7) . . . . ? C48 O5 C47 C36 172.5(4) . . . . ? C48 C49 C50 C51 -0.3(8) . . . . ? C25 C26 C27 C22 0.0(9) . . . . ? C51 C52 C53 C48 -0.5(8) . . . . ? C47 O5 C48 C49 2.2(7) . . . . ? C47 O5 C48 C53 -177.8(4) . . . . ? C47 C36 C35 C61 3.7(7) . . . . ? C47 C36 C35 C34 -178.3(4) . . . . ? C47 C36 C37 C63 1.6(7) . . . . ? C47 C36 C37 C38 -177.0(4) . . . . ? C54 O6 C55 C60 -8.1(8) . . . . ? C54 O6 C55 C56 170.3(5) . . . . ? C49 C48 C53 C52 -0.1(8) . . . . ? C35 C36 C47 O5 91.0(5) . . . . ? C35 C36 C37 C63 -174.1(4) . . . . ? C35 C36 C37 C38 7.2(7) . . . . ? C2 C3 C4 C5 -2.3(7) . . . . ? C2 C3 C4 C32 178.1(4) . . . . ? C2 C3 C14 O2 -87.1(5) . . . . ? C2 C1 C6 C5 0.0(7) . . . . ? C2 C1 C6 C28 177.9(4) . . . . ? C37 C36 C47 O5 -84.9(5) . . . . ? C37 C36 C35 C61 179.4(5) . . . . ? C37 C36 C35 C34 -2.6(7) . . . . ? C5 C4 C32 C33 -88.2(6) . . . . ? C18 C19 C20 C15 -1.0(8) . . . . ? C18 C17 C16 C15 1.5(8) . . . . ? C4 C3 C2 C1 -1.5(7) . . . . ? C4 C3 C2 C30 177.2(4) . . . . ? C4 C3 C14 O2 86.8(5) . . . . ? C4 C5 C21 O3 -92.2(5) . . . . ? C4 C5 C6 C28 178.2(4) . . . . ? C4 C5 C6 C1 -3.9(7) . . . . ? C41 O4 C40 C34 -172.3(4) . . . . ? C41 C42 C43 C44 1.3(8) . . . . ? C41 C46 C45 C44 -1.2(9) . . . . ? C55 O6 C54 C38 -178.9(4) . . . . ? C14 O2 C15 C20 179.8(4) . . . . ? C14 O2 C15 C16 -1.3(7) . . . . ? C14 C3 C2 C1 172.3(4) . . . . ? C14 C3 C2 C30 -9.0(7) . . . . ? C14 C3 C4 C5 -176.1(4) . . . . ? C14 C3 C4 C32 4.3(7) . . . . ? C52 C51 C50 C49 -0.3(8) . . . . ? C15 O2 C14 C3 -177.4(4) . . . . ? C19 C18 C17 C16 -0.1(8) . . . . ? C21 O3 C22 C23 15.4(8) . . . . ? C21 O3 C22 C27 -163.0(5) . . . . ? C21 C5 C4 C3 -177.1(4) . . . . ? C21 C5 C4 C32 2.4(7) . . . . ? C21 C5 C6 C28 0.4(7) . . . . ? C21 C5 C6 C1 178.2(4) . . . . ? C23 C22 C27 C26 0.3(9) . . . . ? C63 C37 C38 C54 4.6(7) . . . . ? C63 C37 C38 C39 178.2(4) . . . . ? C20 C15 C16 C17 -2.7(8) . . . . ? C22 O3 C21 C5 177.5(4) . . . . ? C22 C23 C24 C25 -0.1(10) . . . . ? C13 C8 C9 C10 0.4(8) . . . . ? C50 C51 C52 C53 0.7(8) . . . . ? C61 C35 C34 C39 171.9(4) . . . . ? C61 C35 C34 C40 -14.8(7) . . . . ? C17 C18 C19 C20 -0.2(8) . . . . ? C60 C55 C56 C57 -1.0(8) . . . . ? C60 C59 C58 I6 177.5(5) . . . . ? C60 C59 C58 C57 -2.5(9) . . . . ? C1 C2 C30 C31 96.3(6) . . . . ? C42 C41 C46 C45 0.3(8) . . . . ? C27 C26 C25 I3 180.0(4) . . . . ? C27 C26 C25 C24 -0.3(9) . . . . ? C46 C41 C42 C43 -0.4(8) . . . . ? C16 C15 C20 C19 2.5(8) . . . . ? C58 C57 C56 C55 -0.6(9) . . . . ? C58 C59 C60 C55 0.9(9) . . . . ? C38 C37 C63 C64 84.7(6) . . . . ? C38 C39 C34 C35 10.1(7) . . . . ? C38 C39 C34 C40 -163.3(4) . . . . ? C38 C39 C65 C66 85.0(6) . . . . ? C40 O4 C41 C42 -14.9(7) . . . . ? C40 O4 C41 C46 166.3(5) . . . . ? C30 C2 C1 C7 6.6(7) . . . . ? C30 C2 C1 C6 -176.1(4) . . . . ? C34 C35 C61 C62 -91.2(6) . . . . ? C34 C39 C38 C54 168.2(4) . . . . ? C34 C39 C38 C37 -5.3(7) . . . . ? C34 C39 C65 C66 -96.2(6) . . . . ? C9 C8 C13 C12 0.1(8) . . . . ? C12 C11 C10 C9 -0.1(9) . . . . ? C6 C5 C4 C3 5.0(7) . . . . ? C6 C5 C4 C32 -175.4(4) . . . . ? C6 C5 C21 O3 85.7(6) . . . . ? C43 C44 C45 C46 2.1(9) . . . . ? C10 C11 C12 C13 0.5(9) . . . . ? C24 C23 C22 O3 -178.5(6) . . . . ? C24 C23 C22 C27 -0.2(9) . . . . ? C53 C48 C49 C50 0.5(8) . . . . ? C56 C55 C60 C59 0.9(9) . . . . ? C56 C57 C58 I6 -177.7(4) . . . . ? C56 C57 C58 C59 2.4(9) . . . . ? C65 C39 C38 C54 -13.1(7) . . . . ? C65 C39 C38 C37 173.5(5) . . . . ? C65 C39 C34 C35 -168.7(4) . . . . ? C65 C39 C34 C40 17.9(7) . . . . ? C45 C44 C43 C42 -2.1(9) . . . . ? C29 C28 C6 C5 97.0(6) . . . . ? C29 C28 C6 C1 -80.9(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962419' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-gf-226K _audit_creation_date 2013-12-25 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-gf, 226 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 I3 O3' _chemical_formula_sum 'C33 H33 I3 O3' _chemical_formula_weight 858.29 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.6173(7) _cell_length_b 13.3722(4) _cell_length_c 26.3254(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.829(4) _cell_angle_gamma 90.00 _cell_volume 6536.3(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4202 _cell_measurement_temperature 226(2) _cell_measurement_theta_max 29.0935 _cell_measurement_theta_min 3.6262 _exptl_absorpt_coefficient_mu 2.899 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.57048 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 3312 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.07 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_unetI/netI 0.0789 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 30745 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.16 _diffrn_reflns_theta_min 3.63 _diffrn_ambient_temperature 226(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.845 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0345737000 _diffrn_orient_matrix_UB_12 0.0214003000 _diffrn_orient_matrix_UB_13 -0.0120268000 _diffrn_orient_matrix_UB_21 -0.0089769000 _diffrn_orient_matrix_UB_22 -0.0107717000 _diffrn_orient_matrix_UB_23 0.0234436000 _diffrn_orient_matrix_UB_31 0.0135511000 _diffrn_orient_matrix_UB_32 0.0473347000 _diffrn_orient_matrix_UB_33 0.0107625000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 8369 _reflns_number_total 14919 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 2.199 _refine_diff_density_min -1.672 _refine_diff_density_rms 0.118 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 14919 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0576 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+4.0510P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1084 _refine_ls_wR_factor_ref 0.1373 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C47(H47A,H47B), C54(H54A,H54B), C14(H14A,H14B), C21(H21A,H21B), C63(H63A,H63B), C28(H28A,H28B), C61(H61A,H61B), C40(H40A,H40B), C30(H30A,H30B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C26(H26), C49(H49), C52(H52), C19(H19), C57(H57), C23(H23), C20(H20), C59(H59), C13(H13), C50(H50), C17(H17), C60(H60), C42(H42), C27(H27), C46(H46), C16(H16), C9(H9), C12(H12), C43(H43), C10(H10), C24(H24), C53(H53), C56(H56), C45(H45) 2.c Idealised Me refined as rotating group: C62(H62A,H62B,H62C), C64(H64A,H64B,H64C), C33(H33A,H33B,H33C), C31(H31A,H31B, H31C), C66(H66A,H66B,H66C), C29(H29A,H29B,H29C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I5 I 0.54060(2) 0.69241(4) 0.286624(19) 0.05768(15) Uani 1 1 d . . . I2 I -0.03382(3) 0.30507(4) 0.725986(18) 0.05897(15) Uani 1 1 d . . . I6 I 0.32722(3) 0.45220(4) 0.774617(18) 0.06065(15) Uani 1 1 d . . . I3 I 0.17045(3) 0.56313(4) 0.213151(18) 0.06364(16) Uani 1 1 d . . . I4 I -0.02024(3) 1.53908(3) 0.40908(3) 0.0782(2) Uani 1 1 d . . . I1 I 0.52838(3) -0.52142(4) 0.59448(3) 0.0830(2) Uani 1 1 d . . . O2 O 0.1768(2) 0.1873(3) 0.60286(16) 0.0417(10) Uani 1 1 d . . . O3 O 0.2371(2) 0.2766(3) 0.40932(16) 0.0439(11) Uani 1 1 d . . . O1 O 0.4091(2) -0.0862(3) 0.56906(15) 0.0385(10) Uani 1 1 d . . . O6 O 0.2358(2) 0.7178(3) 0.56937(16) 0.0454(11) Uani 1 1 d . . . O5 O 0.3138(2) 0.8223(3) 0.39357(15) 0.0401(10) Uani 1 1 d . . . C7 C 0.3418(3) -0.0639(4) 0.5291(2) 0.0354(14) Uani 1 1 d . . . H7A H 0.3039 -0.1065 0.5342 0.042 Uiso 1 1 calc . . R H7B H 0.3450 -0.0772 0.4933 0.042 Uiso 1 1 calc . . R C26 C 0.1393(4) 0.4151(5) 0.2906(2) 0.0474(16) Uani 1 1 d . . . H26 H 0.0911 0.4240 0.2690 0.057 Uiso 1 1 calc . . R C8 C 0.4328(3) -0.1829(4) 0.5723(2) 0.0310(13) Uani 1 1 d . . . O4 O 0.0624(2) 1.0878(3) 0.41836(16) 0.0420(10) Uani 1 1 d . . . C3 C 0.2816(3) 0.1771(4) 0.5791(2) 0.0335(13) Uani 1 1 d . . . C36 C 0.2012(3) 0.8268(4) 0.4092(2) 0.0319(13) Uani 1 1 d . . . C48 C 0.3603(3) 0.7927(4) 0.3668(2) 0.0340(13) Uani 1 1 d . . . C25 C 0.1937(4) 0.4661(5) 0.2792(2) 0.0460(16) Uani 1 1 d . . . C51 C 0.4632(3) 0.7386(5) 0.3212(2) 0.0391(15) Uani 1 1 d . . . C47 C 0.2373(3) 0.8005(5) 0.3686(2) 0.0367(14) Uani 1 1 d . . . H47A H 0.2302 0.7295 0.3590 0.044 Uiso 1 1 calc . . R H47B H 0.2173 0.8404 0.3359 0.044 Uiso 1 1 calc . . R C54 C 0.1666(3) 0.7044(4) 0.5285(2) 0.0412(15) Uani 1 1 d . . . H54A H 0.1274 0.7171 0.5432 0.049 Uiso 1 1 calc . . R H54B H 0.1617 0.6361 0.5142 0.049 Uiso 1 1 calc . . R C49 C 0.3399(3) 0.7471(4) 0.3174(2) 0.0355(14) Uani 1 1 d . . . H49 H 0.2910 0.7344 0.2992 0.043 Uiso 1 1 calc . . R C35 C 0.1735(3) 0.9238(4) 0.4102(2) 0.0325(13) Uani 1 1 d . . . C2 C 0.3047(3) 0.0780(4) 0.5777(2) 0.0307(13) Uani 1 1 d . . . C37 C 0.2002(3) 0.7559(4) 0.4483(2) 0.0312(13) Uani 1 1 d . . . C5 C 0.3028(3) 0.2117(4) 0.4954(2) 0.0331(13) Uani 1 1 d . . . C18 C 0.0400(3) 0.2603(4) 0.6879(2) 0.0354(14) Uani 1 1 d . . . C4 C 0.2798(3) 0.2444(4) 0.5377(2) 0.0316(13) Uani 1 1 d . . . C41 C 0.0468(3) 1.1876(4) 0.4189(2) 0.0352(14) Uani 1 1 d . . . C55 C 0.2528(3) 0.6559(4) 0.6137(2) 0.0393(15) Uani 1 1 d . . . C14 C 0.2532(3) 0.2093(5) 0.6233(2) 0.0384(14) Uani 1 1 d . . . H14A H 0.2766 0.1718 0.6563 0.046 Uiso 1 1 calc . . R H14B H 0.2615 0.2809 0.6307 0.046 Uiso 1 1 calc . . R C52 C 0.4839(3) 0.7867(5) 0.3703(3) 0.0439(16) Uani 1 1 d . . . H52 H 0.5327 0.8014 0.3881 0.053 Uiso 1 1 calc . . R C15 C 0.1352(3) 0.2128(4) 0.6340(2) 0.0319(13) Uani 1 1 d . . . C19 C 0.0151(3) 0.2127(4) 0.6382(2) 0.0382(14) Uani 1 1 d . . . H19 H -0.0339 0.1963 0.6231 0.046 Uiso 1 1 calc . . R C21 C 0.3046(3) 0.2834(4) 0.4519(2) 0.0382(14) Uani 1 1 d . . . H21A H 0.3122 0.3517 0.4660 0.046 Uiso 1 1 calc . . R H21B H 0.3443 0.2661 0.4384 0.046 Uiso 1 1 calc . . R C57 C 0.3447(3) 0.6004(5) 0.6928(2) 0.0466(16) Uani 1 1 d . . . H57 H 0.3926 0.6024 0.7158 0.056 Uiso 1 1 calc . . R C23 C 0.2798(4) 0.3909(5) 0.3553(3) 0.0569(19) Uani 1 1 d . . . H23 H 0.3279 0.3819 0.3770 0.068 Uiso 1 1 calc . . R C11 C 0.4888(3) -0.3740(5) 0.5846(3) 0.0471(17) Uani 1 1 d . . . C63 C 0.2370(3) 0.6550(4) 0.4505(2) 0.0372(14) Uani 1 1 d . . . H63A H 0.2766 0.6619 0.4358 0.045 Uiso 1 1 calc . . R H63B H 0.2575 0.6340 0.4881 0.045 Uiso 1 1 calc . . R C20 C 0.0628(3) 0.1897(4) 0.6116(2) 0.0393(15) Uani 1 1 d . . . H20 H 0.0462 0.1582 0.5779 0.047 Uiso 1 1 calc . . R C39 C 0.1320(3) 0.8725(4) 0.4842(2) 0.0332(13) Uani 1 1 d . . . C22 C 0.2261(3) 0.3396(4) 0.3669(2) 0.0389(14) Uani 1 1 d . . . C59 C 0.2259(3) 0.5348(5) 0.6707(3) 0.0521(18) Uani 1 1 d . . . H59 H 0.1928 0.4920 0.6788 0.062 Uiso 1 1 calc . . R C13 C 0.4056(3) -0.2525(4) 0.5323(3) 0.0416(15) Uani 1 1 d . . . H13 H 0.3681 -0.2352 0.5009 0.050 Uiso 1 1 calc . . R C50 C 0.3919(3) 0.7198(4) 0.2945(2) 0.0413(15) Uani 1 1 d . . . H50 H 0.3781 0.6885 0.2608 0.050 Uiso 1 1 calc . . R C28 C 0.3459(3) 0.0774(5) 0.4449(3) 0.0445(16) Uani 1 1 d . . . H28A H 0.3277 0.0098 0.4341 0.053 Uiso 1 1 calc . . R H28B H 0.3253 0.1222 0.4143 0.053 Uiso 1 1 calc . . R C61 C 0.1748(3) 0.9998(4) 0.3682(2) 0.0423(15) Uani 1 1 d . . . H61A H 0.2187 0.9907 0.3587 0.051 Uiso 1 1 calc . . R H61B H 0.1760 1.0671 0.3832 0.051 Uiso 1 1 calc . . R C17 C 0.1122(3) 0.2822(5) 0.7102(2) 0.0409(15) Uani 1 1 d . . . H17 H 0.1289 0.3144 0.7437 0.049 Uiso 1 1 calc . . R C60 C 0.2041(3) 0.5934(5) 0.6252(3) 0.0499(17) Uani 1 1 d . . . H60 H 0.1562 0.5906 0.6021 0.060 Uiso 1 1 calc . . R C44 C 0.0071(3) 1.3860(5) 0.4138(3) 0.0460(16) Uani 1 1 d . . . C1 C 0.3236(3) 0.0439(4) 0.5334(2) 0.0317(13) Uani 1 1 d . . . C42 C 0.0787(3) 1.2509(4) 0.4617(3) 0.0425(15) Uani 1 1 d . . . H42 H 0.1136 1.2264 0.4927 0.051 Uiso 1 1 calc . . R C27 C 0.1560(3) 0.3510(5) 0.3340(2) 0.0448(16) Uani 1 1 d . . . H27 H 0.1191 0.3147 0.3412 0.054 Uiso 1 1 calc . . R C46 C -0.0046(3) 1.2239(5) 0.3731(3) 0.0453(16) Uani 1 1 d . . . H46 H -0.0259 1.1810 0.3440 0.054 Uiso 1 1 calc . . R C16 C 0.1602(3) 0.2572(5) 0.6836(2) 0.0369(14) Uani 1 1 d . . . H16 H 0.2096 0.2705 0.6995 0.044 Uiso 1 1 calc . . R C58 C 0.2960(3) 0.5389(5) 0.7042(2) 0.0413(15) Uani 1 1 d . . . C38 C 0.1644(3) 0.7791(4) 0.4850(2) 0.0319(13) Uani 1 1 d . . . C40 C 0.1251(3) 1.0544(4) 0.4591(2) 0.0393(15) Uani 1 1 d . . . H40A H 0.1178 1.0599 0.4941 0.047 Uiso 1 1 calc . . R H40B H 0.1659 1.0971 0.4596 0.047 Uiso 1 1 calc . . R C30 C 0.3095(3) 0.0072(5) 0.6241(2) 0.0415(15) Uani 1 1 d . . . H30A H 0.2688 0.0200 0.6371 0.050 Uiso 1 1 calc . . R H30B H 0.3053 -0.0618 0.6108 0.050 Uiso 1 1 calc . . R C34 C 0.1421(3) 0.9470(4) 0.4496(2) 0.0329(13) Uani 1 1 d . . . C9 C 0.4872(3) -0.2097(5) 0.6188(3) 0.0453(16) Uani 1 1 d . . . H9 H 0.5050 -0.1626 0.6465 0.054 Uiso 1 1 calc . . R C32 C 0.2541(3) 0.3513(4) 0.5386(3) 0.0412(15) Uani 1 1 d . . . H32A H 0.2180 0.3530 0.5570 0.049 Uiso 1 1 calc . . R H32B H 0.2308 0.3739 0.5016 0.049 Uiso 1 1 calc . . R C62 C 0.1094(4) 0.9907(6) 0.3176(3) 0.064(2) Uani 1 1 d . . . H62A H 0.0658 1.0029 0.3266 0.097 Uiso 1 1 calc . . GR H62B H 0.1077 0.9239 0.3029 0.097 Uiso 1 1 calc . . GR H62C H 0.1130 1.0394 0.2914 0.097 Uiso 1 1 calc . . GR C12 C 0.4342(3) -0.3491(5) 0.5388(3) 0.0504(17) Uani 1 1 d . . . H12 H 0.4160 -0.3971 0.5117 0.061 Uiso 1 1 calc . . R C6 C 0.3228(3) 0.1115(4) 0.4920(2) 0.0354(14) Uani 1 1 d . . . C43 C 0.0585(3) 1.3519(4) 0.4581(3) 0.0459(16) Uani 1 1 d . . . H43 H 0.0806 1.3958 0.4866 0.055 Uiso 1 1 calc . . R C10 C 0.5152(3) -0.3051(5) 0.6247(3) 0.0473(17) Uani 1 1 d . . . H10 H 0.5525 -0.3228 0.6561 0.057 Uiso 1 1 calc . . R C24 C 0.2643(4) 0.4555(5) 0.3121(3) 0.0573(19) Uani 1 1 d . . . H24 H 0.3013 0.4919 0.3051 0.069 Uiso 1 1 calc . . R C64 C 0.1855(4) 0.5748(5) 0.4194(3) 0.0578(19) Uani 1 1 d . . . H64A H 0.1474 0.5653 0.4350 0.087 Uiso 1 1 calc . . GR H64B H 0.2115 0.5125 0.4211 0.087 Uiso 1 1 calc . . GR H64C H 0.1648 0.5954 0.3823 0.087 Uiso 1 1 calc . . GR C33 C 0.3153(4) 0.4233(5) 0.5666(3) 0.0564(19) Uani 1 1 d . . . H33A H 0.3525 0.4192 0.5498 0.085 Uiso 1 1 calc . . GR H33B H 0.3354 0.4053 0.6042 0.085 Uiso 1 1 calc . . GR H33C H 0.2968 0.4911 0.5636 0.085 Uiso 1 1 calc . . GR C53 C 0.4319(3) 0.8129(5) 0.3928(2) 0.0423(15) Uani 1 1 d . . . H53 H 0.4455 0.8450 0.4264 0.051 Uiso 1 1 calc . . R C56 C 0.3232(3) 0.6603(5) 0.6469(2) 0.0452(16) Uani 1 1 d . . . H56 H 0.3563 0.7030 0.6388 0.054 Uiso 1 1 calc . . R C65 C 0.0851(3) 0.8938(5) 0.5191(2) 0.0431(15) Uani 1 1 d . . . H65A H 0.0507 0.9464 0.5019 0.052 Uiso 1 1 calc . . R H65B H 0.0573 0.8334 0.5204 0.052 Uiso 1 1 calc . . R C45 C -0.0242(3) 1.3232(5) 0.3705(3) 0.0509(18) Uani 1 1 d . . . H45 H -0.0587 1.3485 0.3394 0.061 Uiso 1 1 calc . . R C31 C 0.3792(4) 0.0178(6) 0.6705(3) 0.062(2) Uani 1 1 d . . . H31A H 0.4198 0.0064 0.6578 0.093 Uiso 1 1 calc . . GR H31B H 0.3801 -0.0309 0.6981 0.093 Uiso 1 1 calc . . GR H31C H 0.3822 0.0847 0.6854 0.093 Uiso 1 1 calc . . GR C66 C 0.1254(4) 0.9259(5) 0.5765(2) 0.0542(18) Uani 1 1 d . . . H66A H 0.1587 0.8736 0.5944 0.081 Uiso 1 1 calc . . GR H66B H 0.0912 0.9374 0.5955 0.081 Uiso 1 1 calc . . GR H66C H 0.1518 0.9870 0.5760 0.081 Uiso 1 1 calc . . GR C29 C 0.4268(4) 0.0778(6) 0.4600(3) 0.068(2) Uani 1 1 d . . . H29A H 0.4408 0.0519 0.4304 0.102 Uiso 1 1 calc . . GR H29B H 0.4472 0.0362 0.4914 0.102 Uiso 1 1 calc . . GR H29C H 0.4445 0.1457 0.4680 0.102 Uiso 1 1 calc . . GR 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 I5 0.0521(3) 0.0739(3) 0.0564(3) -0.0107(3) 0.0304(2) 0.0043(2) I2 0.0567(3) 0.0790(4) 0.0498(3) -0.0093(3) 0.0291(2) 0.0063(3) I6 0.0701(3) 0.0717(3) 0.0382(3) 0.0169(2) 0.0147(2) 0.0179(3) I3 0.0740(3) 0.0757(4) 0.0429(3) 0.0181(3) 0.0214(2) 0.0233(3) I4 0.0506(3) 0.0330(2) 0.1408(6) 0.0221(3) 0.0166(3) 0.0099(2) I1 0.0564(3) 0.0365(3) 0.1443(6) 0.0240(3) 0.0161(3) 0.0148(2) O2 0.038(2) 0.048(3) 0.040(2) -0.015(2) 0.0149(19) -0.002(2) O3 0.039(2) 0.045(3) 0.045(3) 0.014(2) 0.008(2) -0.002(2) O1 0.039(2) 0.028(2) 0.041(2) -0.002(2) 0.0035(19) 0.0061(18) O6 0.049(3) 0.042(2) 0.042(3) 0.014(2) 0.011(2) -0.006(2) O5 0.039(2) 0.046(2) 0.039(2) -0.013(2) 0.0169(19) 0.002(2) C7 0.039(3) 0.029(3) 0.033(3) -0.001(3) 0.005(3) 0.004(3) C26 0.049(4) 0.049(4) 0.040(4) -0.006(3) 0.009(3) 0.002(3) C8 0.034(3) 0.030(3) 0.032(3) 0.002(3) 0.015(3) 0.005(3) O4 0.042(2) 0.030(2) 0.051(3) 0.002(2) 0.009(2) 0.0085(19) C3 0.029(3) 0.033(3) 0.035(3) -0.004(3) 0.006(2) 0.002(3) C36 0.031(3) 0.035(3) 0.029(3) -0.001(3) 0.009(2) 0.006(3) C48 0.045(4) 0.028(3) 0.030(3) -0.004(3) 0.013(3) 0.003(3) C25 0.056(4) 0.044(4) 0.043(4) 0.002(3) 0.021(3) 0.016(3) C51 0.039(3) 0.039(3) 0.043(4) 0.006(3) 0.018(3) 0.006(3) C47 0.032(3) 0.042(3) 0.038(3) -0.001(3) 0.013(3) 0.004(3) C54 0.043(4) 0.038(3) 0.043(4) 0.006(3) 0.014(3) -0.002(3) C49 0.038(3) 0.035(3) 0.033(3) -0.001(3) 0.011(3) 0.003(3) C35 0.035(3) 0.034(3) 0.030(3) -0.002(3) 0.013(3) 0.000(3) C2 0.027(3) 0.028(3) 0.037(3) 0.002(3) 0.011(2) 0.000(2) C37 0.032(3) 0.025(3) 0.035(3) -0.001(3) 0.009(3) 0.004(2) C5 0.026(3) 0.029(3) 0.039(3) 0.005(3) 0.003(3) -0.002(2) C18 0.038(3) 0.035(3) 0.036(3) 0.008(3) 0.017(3) 0.007(3) C4 0.032(3) 0.027(3) 0.035(3) -0.004(3) 0.008(3) 0.004(3) C41 0.034(3) 0.033(3) 0.041(4) 0.004(3) 0.015(3) 0.003(3) C55 0.051(4) 0.029(3) 0.038(4) 0.005(3) 0.015(3) 0.003(3) C14 0.033(3) 0.039(3) 0.041(4) -0.004(3) 0.010(3) -0.001(3) C52 0.041(4) 0.043(4) 0.050(4) -0.010(3) 0.018(3) -0.006(3) C15 0.037(3) 0.027(3) 0.032(3) -0.003(3) 0.011(3) 0.006(3) C19 0.036(3) 0.037(3) 0.042(4) -0.006(3) 0.013(3) -0.005(3) C21 0.042(4) 0.033(3) 0.042(4) 0.007(3) 0.016(3) 0.001(3) C57 0.043(4) 0.054(4) 0.035(4) -0.007(3) 0.001(3) -0.007(3) C23 0.045(4) 0.065(5) 0.063(5) 0.031(4) 0.021(3) 0.015(4) C11 0.047(4) 0.030(3) 0.064(5) 0.010(4) 0.017(3) 0.008(3) C63 0.039(3) 0.030(3) 0.041(4) -0.005(3) 0.010(3) 0.003(3) C20 0.041(4) 0.042(4) 0.035(3) -0.009(3) 0.013(3) 0.002(3) C39 0.032(3) 0.032(3) 0.035(3) -0.002(3) 0.010(3) -0.001(3) C22 0.046(4) 0.035(3) 0.040(4) 0.004(3) 0.019(3) 0.005(3) C59 0.038(4) 0.057(4) 0.064(5) 0.024(4) 0.019(3) 0.003(3) C13 0.036(3) 0.037(3) 0.044(4) -0.001(3) 0.003(3) 0.005(3) C50 0.050(4) 0.038(3) 0.035(3) -0.007(3) 0.013(3) 0.006(3) C28 0.051(4) 0.038(3) 0.048(4) 0.007(3) 0.022(3) 0.011(3) C61 0.051(4) 0.033(3) 0.047(4) 0.011(3) 0.021(3) 0.007(3) C17 0.046(4) 0.042(4) 0.030(3) -0.007(3) 0.006(3) 0.002(3) C60 0.031(3) 0.059(4) 0.055(4) 0.026(4) 0.008(3) 0.003(3) C44 0.041(4) 0.033(3) 0.065(5) 0.003(4) 0.018(3) 0.005(3) C1 0.029(3) 0.031(3) 0.032(3) 0.004(3) 0.005(2) 0.003(3) C42 0.041(4) 0.033(3) 0.049(4) 0.006(3) 0.008(3) 0.005(3) C27 0.041(4) 0.044(4) 0.045(4) -0.002(3) 0.009(3) -0.006(3) C46 0.043(4) 0.047(4) 0.047(4) -0.001(3) 0.016(3) 0.003(3) C16 0.031(3) 0.045(4) 0.034(3) -0.003(3) 0.008(3) 0.000(3) C58 0.053(4) 0.041(4) 0.033(3) 0.008(3) 0.019(3) 0.008(3) C38 0.035(3) 0.025(3) 0.035(3) 0.003(3) 0.010(3) 0.000(3) C40 0.042(4) 0.032(3) 0.042(4) 0.003(3) 0.011(3) 0.006(3) C30 0.046(4) 0.037(3) 0.044(4) 0.003(3) 0.018(3) 0.000(3) C34 0.037(3) 0.025(3) 0.036(3) 0.005(3) 0.010(3) 0.008(3) C9 0.042(4) 0.046(4) 0.040(4) 0.000(3) 0.003(3) -0.001(3) C32 0.040(3) 0.027(3) 0.054(4) 0.001(3) 0.011(3) 0.007(3) C62 0.073(5) 0.064(5) 0.054(5) 0.031(4) 0.018(4) 0.013(4) C12 0.048(4) 0.034(3) 0.062(5) -0.004(4) 0.008(3) 0.006(3) C6 0.031(3) 0.035(3) 0.038(3) 0.003(3) 0.009(3) 0.006(3) C43 0.038(4) 0.033(3) 0.059(4) 0.002(3) 0.005(3) 0.009(3) C10 0.045(4) 0.050(4) 0.041(4) 0.018(4) 0.006(3) 0.007(3) C24 0.049(4) 0.065(5) 0.062(5) 0.024(4) 0.024(4) 0.006(4) C64 0.060(5) 0.036(4) 0.071(5) -0.011(4) 0.013(4) -0.001(3) C33 0.064(5) 0.030(3) 0.070(5) -0.009(4) 0.014(4) -0.007(3) C53 0.040(4) 0.050(4) 0.037(4) -0.010(3) 0.013(3) -0.006(3) C56 0.043(4) 0.051(4) 0.038(4) -0.004(3) 0.008(3) -0.010(3) C65 0.043(4) 0.042(4) 0.046(4) 0.001(3) 0.018(3) 0.001(3) C45 0.040(4) 0.054(4) 0.058(5) 0.022(4) 0.015(3) 0.012(3) C31 0.065(5) 0.068(5) 0.047(4) 0.014(4) 0.010(4) 0.012(4) C66 0.058(4) 0.059(4) 0.048(4) -0.014(4) 0.020(3) -0.011(4) C29 0.058(5) 0.076(5) 0.076(5) 0.011(5) 0.031(4) 0.012(4) _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 I5 C51 2.099(6) . ? I2 C18 2.098(6) . ? I6 C58 2.104(6) . ? I3 C25 2.098(6) . ? I4 C44 2.109(6) . ? I1 C11 2.103(6) . ? O2 C14 1.451(6) . ? O2 C15 1.373(6) . ? O3 C21 1.435(7) . ? O3 C22 1.360(7) . ? O1 C7 1.429(6) . ? O1 C8 1.368(6) . ? O6 C54 1.446(7) . ? O6 C55 1.381(7) . ? O5 C48 1.379(6) . ? O5 C47 1.459(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 C1 1.498(7) . ? C26 H26 0.9400 . ? C26 C25 1.379(9) . ? C26 C27 1.381(8) . ? C8 C13 1.377(8) . ? C8 C9 1.387(8) . ? O4 C41 1.370(6) . ? O4 C40 1.418(6) . ? C3 C2 1.404(7) . ? C3 C4 1.405(8) . ? C3 C14 1.505(8) . ? C36 C47 1.502(7) . ? C36 C35 1.411(7) . ? C36 C37 1.404(8) . ? C48 C49 1.373(7) . ? C48 C53 1.376(8) . ? C25 C24 1.382(9) . ? C51 C52 1.383(8) . ? C51 C50 1.371(8) . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 C38 1.509(8) . ? C49 H49 0.9400 . ? C49 C50 1.390(8) . ? C35 C61 1.507(8) . ? C35 C34 1.402(7) . ? C2 C1 1.409(7) . ? C2 C30 1.524(8) . ? C37 C63 1.523(7) . ? C37 C38 1.400(7) . ? C5 C4 1.400(8) . ? C5 C21 1.503(8) . ? C5 C6 1.408(7) . ? C18 C19 1.393(8) . ? C18 C17 1.378(8) . ? C4 C32 1.518(7) . ? C41 C42 1.386(8) . ? C41 C46 1.386(8) . ? C55 C60 1.374(8) . ? C55 C56 1.377(8) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C52 H52 0.9400 . ? C52 C53 1.381(8) . ? C15 C20 1.386(8) . ? C15 C16 1.374(7) . ? C19 H19 0.9400 . ? C19 C20 1.373(8) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C57 H57 0.9400 . ? C57 C58 1.364(8) . ? C57 C56 1.396(8) . ? C23 H23 0.9400 . ? C23 C22 1.371(8) . ? C23 C24 1.382(9) . ? C11 C12 1.369(9) . ? C11 C10 1.372(9) . ? C63 H63A 0.9800 . ? C63 H63B 0.9800 . ? C63 C64 1.518(8) . ? C20 H20 0.9400 . ? C39 C38 1.398(7) . ? C39 C34 1.408(8) . ? C39 C65 1.522(8) . ? C22 C27 1.377(8) . ? C59 H59 0.9400 . ? C59 C60 1.379(8) . ? C59 C58 1.375(8) . ? C13 H13 0.9400 . ? C13 C12 1.397(8) . ? C50 H50 0.9400 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 C6 1.523(8) . ? C28 C29 1.506(8) . ? C61 H61A 0.9800 . ? C61 H61B 0.9800 . ? C61 C62 1.527(9) . ? C17 H17 0.9400 . ? C17 C16 1.382(8) . ? C60 H60 0.9400 . ? C44 C43 1.352(8) . ? C44 C45 1.389(9) . ? C1 C6 1.412(8) . ? C42 H42 0.9400 . ? C42 C43 1.402(8) . ? C27 H27 0.9400 . ? C46 H46 0.9400 . ? C46 C45 1.379(9) . ? C16 H16 0.9400 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 C34 1.513(7) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 C31 1.519(8) . ? C9 H9 0.9400 . ? C9 C10 1.378(8) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 C33 1.531(8) . ? C62 H62A 0.9700 . ? C62 H62B 0.9700 . ? C62 H62C 0.9700 . ? C12 H12 0.9400 . ? C43 H43 0.9400 . ? C10 H10 0.9400 . ? C24 H24 0.9400 . ? C64 H64A 0.9700 . ? C64 H64B 0.9700 . ? C64 H64C 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C53 H53 0.9400 . ? C56 H56 0.9400 . ? C65 H65A 0.9800 . ? C65 H65B 0.9800 . ? C65 C66 1.522(8) . ? C45 H45 0.9400 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 H31C 0.9700 . ? C66 H66A 0.9700 . ? C66 H66B 0.9700 . ? C66 H66C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O2 C14 118.1(4) . . ? C22 O3 C21 117.7(4) . . ? C8 O1 C7 117.2(4) . . ? C55 O6 C54 117.9(4) . . ? C48 O5 C47 117.8(4) . . ? O1 C7 H7A 109.8 . . ? O1 C7 H7B 109.8 . . ? O1 C7 C1 109.3(4) . . ? H7A C7 H7B 108.3 . . ? C1 C7 H7A 109.8 . . ? C1 C7 H7B 109.8 . . ? C25 C26 H26 120.2 . . ? C25 C26 C27 119.5(6) . . ? C27 C26 H26 120.2 . . ? O1 C8 C13 123.5(5) . . ? O1 C8 C9 116.6(5) . . ? C13 C8 C9 120.0(5) . . ? C41 O4 C40 116.2(4) . . ? C2 C3 C4 120.7(5) . . ? C2 C3 C14 119.6(5) . . ? C4 C3 C14 119.5(5) . . ? C35 C36 C47 120.1(5) . . ? C37 C36 C47 119.0(5) . . ? C37 C36 C35 120.7(5) . . ? C49 C48 O5 124.9(5) . . ? C49 C48 C53 119.8(5) . . ? C53 C48 O5 115.3(5) . . ? C26 C25 I3 120.6(5) . . ? C26 C25 C24 120.1(6) . . ? C24 C25 I3 119.2(5) . . ? C52 C51 I5 120.4(4) . . ? C50 C51 I5 119.1(5) . . ? C50 C51 C52 120.5(6) . . ? O5 C47 C36 106.5(4) . . ? O5 C47 H47A 110.4 . . ? O5 C47 H47B 110.4 . . ? C36 C47 H47A 110.4 . . ? C36 C47 H47B 110.4 . . ? H47A C47 H47B 108.6 . . ? O6 C54 H54A 110.6 . . ? O6 C54 H54B 110.6 . . ? O6 C54 C38 105.8(4) . . ? H54A C54 H54B 108.7 . . ? C38 C54 H54A 110.6 . . ? C38 C54 H54B 110.6 . . ? C48 C49 H49 120.1 . . ? C48 C49 C50 119.8(6) . . ? C50 C49 H49 120.1 . . ? C36 C35 C61 120.6(5) . . ? C34 C35 C36 118.8(5) . . ? C34 C35 C61 120.6(5) . . ? C3 C2 C1 120.1(5) . . ? C3 C2 C30 120.1(5) . . ? C1 C2 C30 119.7(5) . . ? C36 C37 C63 120.5(5) . . ? C38 C37 C36 119.0(5) . . ? C38 C37 C63 120.4(5) . . ? C4 C5 C21 120.1(5) . . ? C4 C5 C6 121.0(5) . . ? C6 C5 C21 118.9(5) . . ? C19 C18 I2 119.4(4) . . ? C17 C18 I2 120.6(4) . . ? C17 C18 C19 119.9(5) . . ? C3 C4 C32 121.1(5) . . ? C5 C4 C3 118.9(5) . . ? C5 C4 C32 119.9(5) . . ? O4 C41 C42 124.0(5) . . ? O4 C41 C46 115.7(5) . . ? C42 C41 C46 120.3(6) . . ? C60 C55 O6 123.7(6) . . ? C60 C55 C56 120.8(6) . . ? C56 C55 O6 115.5(5) . . ? O2 C14 C3 104.5(4) . . ? O2 C14 H14A 110.8 . . ? O2 C14 H14B 110.8 . . ? C3 C14 H14A 110.8 . . ? C3 C14 H14B 110.8 . . ? H14A C14 H14B 108.9 . . ? C51 C52 H52 120.5 . . ? C53 C52 C51 118.9(6) . . ? C53 C52 H52 120.5 . . ? O2 C15 C20 114.6(5) . . ? O2 C15 C16 125.2(5) . . ? C16 C15 C20 120.2(5) . . ? C18 C19 H19 120.3 . . ? C20 C19 C18 119.4(6) . . ? C20 C19 H19 120.3 . . ? O3 C21 C5 108.2(4) . . ? O3 C21 H21A 110.1 . . ? O3 C21 H21B 110.1 . . ? C5 C21 H21A 110.1 . . ? C5 C21 H21B 110.1 . . ? H21A C21 H21B 108.4 . . ? C58 C57 H57 120.1 . . ? C58 C57 C56 119.8(6) . . ? C56 C57 H57 120.1 . . ? C22 C23 H23 119.5 . . ? C22 C23 C24 120.9(6) . . ? C24 C23 H23 119.5 . . ? C12 C11 I1 119.3(5) . . ? C12 C11 C10 120.5(6) . . ? C10 C11 I1 120.1(5) . . ? C37 C63 H63A 109.1 . . ? C37 C63 H63B 109.1 . . ? H63A C63 H63B 107.9 . . ? C64 C63 C37 112.4(5) . . ? C64 C63 H63A 109.1 . . ? C64 C63 H63B 109.1 . . ? C15 C20 H20 119.8 . . ? C19 C20 C15 120.5(6) . . ? C19 C20 H20 119.8 . . ? C38 C39 C34 118.9(5) . . ? C38 C39 C65 121.3(5) . . ? C34 C39 C65 119.8(5) . . ? O3 C22 C23 124.3(6) . . ? O3 C22 C27 116.5(6) . . ? C23 C22 C27 119.3(6) . . ? C60 C59 H59 120.0 . . ? C58 C59 H59 120.0 . . ? C58 C59 C60 120.0(6) . . ? C8 C13 H13 120.4 . . ? C8 C13 C12 119.3(6) . . ? C12 C13 H13 120.4 . . ? C51 C50 C49 120.0(6) . . ? C51 C50 H50 120.0 . . ? C49 C50 H50 120.0 . . ? H28A C28 H28B 108.1 . . ? C6 C28 H28A 109.6 . . ? C6 C28 H28B 109.6 . . ? C29 C28 H28A 109.6 . . ? C29 C28 H28B 109.6 . . ? C29 C28 C6 110.4(5) . . ? C35 C61 H61A 109.2 . . ? C35 C61 H61B 109.2 . . ? C35 C61 C62 112.2(5) . . ? H61A C61 H61B 107.9 . . ? C62 C61 H61A 109.2 . . ? C62 C61 H61B 109.2 . . ? C18 C17 H17 119.8 . . ? C18 C17 C16 120.5(6) . . ? C16 C17 H17 119.8 . . ? C55 C60 C59 119.6(6) . . ? C55 C60 H60 120.2 . . ? C59 C60 H60 120.2 . . ? C43 C44 I4 118.9(5) . . ? C43 C44 C45 120.9(6) . . ? C45 C44 I4 120.1(5) . . ? C2 C1 C7 120.5(5) . . ? C2 C1 C6 119.3(5) . . ? C6 C1 C7 120.1(5) . . ? C41 C42 H42 120.3 . . ? C41 C42 C43 119.4(6) . . ? C43 C42 H42 120.3 . . ? C26 C27 H27 119.6 . . ? C22 C27 C26 120.7(6) . . ? C22 C27 H27 119.6 . . ? C41 C46 H46 120.2 . . ? C45 C46 C41 119.6(6) . . ? C45 C46 H46 120.2 . . ? C15 C16 C17 119.5(5) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C57 C58 I6 120.0(5) . . ? C57 C58 C59 120.7(6) . . ? C59 C58 I6 119.3(5) . . ? C37 C38 C54 118.6(5) . . ? C39 C38 C54 120.2(5) . . ? C39 C38 C37 121.0(5) . . ? O4 C40 H40A 109.4 . . ? O4 C40 H40B 109.4 . . ? O4 C40 C34 111.0(5) . . ? H40A C40 H40B 108.0 . . ? C34 C40 H40A 109.4 . . ? C34 C40 H40B 109.4 . . ? C2 C30 H30A 108.9 . . ? C2 C30 H30B 108.9 . . ? H30A C30 H30B 107.8 . . ? C31 C30 C2 113.2(5) . . ? C31 C30 H30A 108.9 . . ? C31 C30 H30B 108.9 . . ? C35 C34 C39 120.7(5) . . ? C35 C34 C40 120.3(5) . . ? C39 C34 C40 118.8(5) . . ? C8 C9 H9 119.9 . . ? C10 C9 C8 120.2(6) . . ? C10 C9 H9 119.9 . . ? C4 C32 H32A 109.0 . . ? C4 C32 H32B 109.0 . . ? C4 C32 C33 112.8(5) . . ? H32A C32 H32B 107.8 . . ? C33 C32 H32A 109.0 . . ? C33 C32 H32B 109.0 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C11 C12 C13 120.2(6) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C5 C6 C28 119.9(5) . . ? C5 C6 C1 119.7(5) . . ? C1 C6 C28 120.4(5) . . ? C44 C43 C42 119.9(6) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C11 C10 C9 119.9(6) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C25 C24 H24 120.3 . . ? C23 C24 C25 119.4(6) . . ? C23 C24 H24 120.3 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C48 C53 C52 120.9(6) . . ? C48 C53 H53 119.5 . . ? C52 C53 H53 119.5 . . ? C55 C56 C57 119.1(6) . . ? C55 C56 H56 120.4 . . ? C57 C56 H56 120.4 . . ? C39 C65 H65A 108.4 . . ? C39 C65 H65B 108.4 . . ? H65A C65 H65B 107.5 . . ? C66 C65 C39 115.5(5) . . ? C66 C65 H65A 108.4 . . ? C66 C65 H65B 108.4 . . ? C44 C45 H45 120.0 . . ? C46 C45 C44 119.9(6) . . ? C46 C45 H45 120.0 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I5 C51 C52 C53 -177.7(5) . . . . ? I5 C51 C50 C49 178.1(4) . . . . ? I2 C18 C19 C20 175.5(4) . . . . ? I2 C18 C17 C16 -176.7(4) . . . . ? I3 C25 C24 C23 -179.4(5) . . . . ? I4 C44 C43 C42 -178.5(5) . . . . ? I4 C44 C45 C46 178.0(5) . . . . ? I1 C11 C12 C13 177.9(5) . . . . ? I1 C11 C10 C9 -177.5(5) . . . . ? O2 C15 C20 C19 -179.0(5) . . . . ? O2 C15 C16 C17 177.8(5) . . . . ? O3 C22 C27 C26 178.5(6) . . . . ? O1 C7 C1 C2 -69.8(7) . . . . ? O1 C7 C1 C6 112.6(6) . . . . ? O1 C8 C13 C12 178.8(5) . . . . ? O1 C8 C9 C10 -178.5(5) . . . . ? O6 C54 C38 C37 79.9(6) . . . . ? O6 C54 C38 C39 -95.3(6) . . . . ? O6 C55 C60 C59 -179.5(6) . . . . ? O6 C55 C56 C57 179.7(6) . . . . ? O5 C48 C49 C50 -179.5(5) . . . . ? O5 C48 C53 C52 179.8(5) . . . . ? C7 O1 C8 C13 16.1(8) . . . . ? C7 O1 C8 C9 -163.8(5) . . . . ? C7 C1 C6 C5 177.4(5) . . . . ? C7 C1 C6 C28 -4.7(8) . . . . ? C26 C25 C24 C23 2.3(10) . . . . ? C8 O1 C7 C1 177.6(4) . . . . ? C8 C13 C12 C11 0.1(10) . . . . ? C8 C9 C10 C11 -0.7(10) . . . . ? O4 C41 C42 C43 -179.6(5) . . . . ? O4 C41 C46 C45 179.2(5) . . . . ? O4 C40 C34 C35 76.4(7) . . . . ? O4 C40 C34 C39 -109.3(6) . . . . ? C3 C2 C1 C7 -174.4(5) . . . . ? C3 C2 C1 C6 3.3(8) . . . . ? C3 C2 C30 C31 -83.3(7) . . . . ? C3 C4 C32 C33 90.8(7) . . . . ? C36 C35 C61 C62 85.6(7) . . . . ? C36 C35 C34 C39 -6.2(8) . . . . ? C36 C35 C34 C40 168.0(5) . . . . ? C36 C37 C63 C64 -93.8(7) . . . . ? C36 C37 C38 C54 -177.1(5) . . . . ? C36 C37 C38 C39 -2.0(8) . . . . ? C48 O5 C47 C36 172.1(5) . . . . ? C48 C49 C50 C51 -0.1(9) . . . . ? C25 C26 C27 C22 1.9(9) . . . . ? C51 C52 C53 C48 -0.7(9) . . . . ? C47 O5 C48 C49 2.3(8) . . . . ? C47 O5 C48 C53 -178.4(5) . . . . ? C47 C36 C35 C61 4.5(8) . . . . ? C47 C36 C35 C34 -178.0(5) . . . . ? C47 C36 C37 C63 1.8(8) . . . . ? C47 C36 C37 C38 -177.8(5) . . . . ? C54 O6 C55 C60 -10.3(8) . . . . ? C54 O6 C55 C56 169.8(5) . . . . ? C49 C48 C53 C52 -0.9(9) . . . . ? C35 C36 C47 O5 90.8(6) . . . . ? C35 C36 C37 C63 -173.7(5) . . . . ? C35 C36 C37 C38 6.6(8) . . . . ? C2 C3 C4 C5 -1.2(8) . . . . ? C2 C3 C4 C32 179.2(5) . . . . ? C2 C3 C14 O2 -88.5(6) . . . . ? C2 C1 C6 C5 -0.3(8) . . . . ? C2 C1 C6 C28 177.6(5) . . . . ? C37 C36 C47 O5 -84.7(6) . . . . ? C37 C36 C35 C61 180.0(5) . . . . ? C37 C36 C35 C34 -2.6(8) . . . . ? C5 C4 C32 C33 -88.8(7) . . . . ? C18 C19 C20 C15 0.7(9) . . . . ? C18 C17 C16 C15 1.8(9) . . . . ? C4 C3 C2 C1 -2.6(8) . . . . ? C4 C3 C2 C30 177.3(5) . . . . ? C4 C3 C14 O2 86.9(6) . . . . ? C4 C5 C21 O3 -92.2(6) . . . . ? C4 C5 C6 C28 178.6(5) . . . . ? C4 C5 C6 C1 -3.5(8) . . . . ? C41 O4 C40 C34 -172.1(5) . . . . ? C41 C42 C43 C44 1.4(9) . . . . ? C41 C46 C45 C44 -0.5(10) . . . . ? C55 O6 C54 C38 -178.3(5) . . . . ? C14 O2 C15 C20 179.7(5) . . . . ? C14 O2 C15 C16 -0.5(8) . . . . ? C14 C3 C2 C1 172.9(5) . . . . ? C14 C3 C2 C30 -7.3(8) . . . . ? C14 C3 C4 C5 -176.6(5) . . . . ? C14 C3 C4 C32 3.8(8) . . . . ? C52 C51 C50 C49 -1.5(9) . . . . ? C15 O2 C14 C3 -177.4(5) . . . . ? C19 C18 C17 C16 0.0(9) . . . . ? C21 O3 C22 C23 16.8(9) . . . . ? C21 O3 C22 C27 -163.4(5) . . . . ? C21 C5 C4 C3 -177.3(5) . . . . ? C21 C5 C4 C32 2.3(8) . . . . ? C21 C5 C6 C28 0.0(8) . . . . ? C21 C5 C6 C1 178.0(5) . . . . ? C23 C22 C27 C26 -1.7(10) . . . . ? C63 C37 C38 C54 3.2(8) . . . . ? C63 C37 C38 C39 178.3(5) . . . . ? C20 C15 C16 C17 -2.4(9) . . . . ? C22 O3 C21 C5 176.7(5) . . . . ? C22 C23 C24 C25 -2.1(11) . . . . ? C13 C8 C9 C10 1.5(9) . . . . ? C50 C51 C52 C53 1.9(9) . . . . ? C61 C35 C34 C39 171.2(5) . . . . ? C61 C35 C34 C40 -14.6(8) . . . . ? C17 C18 C19 C20 -1.3(9) . . . . ? C60 C55 C56 C57 -0.2(9) . . . . ? C60 C59 C58 I6 178.1(5) . . . . ? C60 C59 C58 C57 -0.2(10) . . . . ? C1 C2 C30 C31 96.6(6) . . . . ? C42 C41 C46 C45 -0.5(9) . . . . ? C27 C26 C25 I3 179.4(5) . . . . ? C27 C26 C25 C24 -2.2(9) . . . . ? C46 C41 C42 C43 0.1(9) . . . . ? C16 C15 C20 C19 1.2(9) . . . . ? C58 C57 C56 C55 -0.2(10) . . . . ? C58 C59 C60 C55 -0.2(11) . . . . ? C38 C37 C63 C64 85.9(7) . . . . ? C38 C39 C34 C35 10.7(8) . . . . ? C38 C39 C34 C40 -163.5(5) . . . . ? C38 C39 C65 C66 84.5(7) . . . . ? C40 O4 C41 C42 -13.7(8) . . . . ? C40 O4 C41 C46 166.6(5) . . . . ? C30 C2 C1 C7 5.8(8) . . . . ? C30 C2 C1 C6 -176.5(5) . . . . ? C34 C35 C61 C62 -91.8(7) . . . . ? C34 C39 C38 C54 168.5(5) . . . . ? C34 C39 C38 C37 -6.6(8) . . . . ? C34 C39 C65 C66 -96.7(7) . . . . ? C9 C8 C13 C12 -1.2(9) . . . . ? C12 C11 C10 C9 -0.5(10) . . . . ? C6 C5 C4 C3 4.3(8) . . . . ? C6 C5 C4 C32 -176.2(5) . . . . ? C6 C5 C21 O3 86.3(6) . . . . ? C43 C44 C45 C46 2.1(10) . . . . ? C10 C11 C12 C13 0.8(10) . . . . ? C24 C23 C22 O3 -178.4(6) . . . . ? C24 C23 C22 C27 1.8(10) . . . . ? C53 C48 C49 C50 1.3(9) . . . . ? C56 C55 C60 C59 0.5(10) . . . . ? C56 C57 C58 I6 -177.9(5) . . . . ? C56 C57 C58 C59 0.4(10) . . . . ? C65 C39 C38 C54 -12.8(8) . . . . ? C65 C39 C38 C37 172.2(5) . . . . ? C65 C39 C34 C35 -168.0(5) . . . . ? C65 C39 C34 C40 17.7(8) . . . . ? C45 C44 C43 C42 -2.5(10) . . . . ? C29 C28 C6 C5 96.9(6) . . . . ? C29 C28 C6 C1 -81.0(7) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962420' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-gf-262K _audit_creation_date 2013-12-25 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-gf, 262 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 I3 O3' _chemical_formula_sum 'C33 H33 I3 O3' _chemical_formula_weight 858.29 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.7104(9) _cell_length_b 13.3901(5) _cell_length_c 26.3231(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.829(5) _cell_angle_gamma 90.00 _cell_volume 6575.5(5) _cell_formula_units_Z 8 _cell_measurement_reflns_used 3511 _cell_measurement_temperature 262(2) _cell_measurement_theta_max 29.0859 _cell_measurement_theta_min 3.6224 _exptl_absorpt_coefficient_mu 2.882 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.49104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.734 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 3312 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.07 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_unetI/netI 0.0822 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 30554 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.15 _diffrn_reflns_theta_min 3.63 _diffrn_ambient_temperature 262(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.844 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0344667000 _diffrn_orient_matrix_UB_12 0.0211689000 _diffrn_orient_matrix_UB_13 -0.0120656000 _diffrn_orient_matrix_UB_21 -0.0088707000 _diffrn_orient_matrix_UB_22 -0.0105697000 _diffrn_orient_matrix_UB_23 0.0234952000 _diffrn_orient_matrix_UB_31 0.0133801000 _diffrn_orient_matrix_UB_32 0.0474029000 _diffrn_orient_matrix_UB_33 0.0106162000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 7380 _reflns_number_total 14981 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 2.027 _refine_diff_density_min -1.660 _refine_diff_density_rms 0.110 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 709 _refine_ls_number_reflns 14981 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1501 _refine_ls_R_factor_gt 0.0625 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+6.2648P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1214 _refine_ls_wR_factor_ref 0.1596 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C47(H47A,H47B), C54(H54A,H54B), C14(H14A,H14B), C21(H21A,H21B), C63(H63A,H63B), C28(H28A,H28B), C61(H61A,H61B), C40(H40A,H40B), C30(H30A,H30B), C32(H32A,H32B), C65(H65A,H65B) 2.b Aromatic/amide H refined with riding coordinates: C26(H26), C49(H49), C52(H52), C19(H19), C57(H57), C23(H23), C20(H20), C59(H59), C13(H13), C50(H50), C17(H17), C60(H60), C42(H42), C27(H27), C46(H46), C16(H16), C9(H9), C12(H12), C43(H43), C10(H10), C24(H24), C53(H53), C56(H56), C45(H45) 2.c Idealised Me refined as rotating group: C62(H62A,H62B,H62C), C64(H64A,H64B,H64C), C33(H33A,H33B,H33C), C31(H31A,H31B, H31C), C66(H66A,H66B,H66C), C29(H29A,H29B,H29C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I5 I 0.53939(3) 0.69297(5) 0.28613(2) 0.06964(19) Uani 1 1 d . . . I2 I -0.03341(3) 0.30504(5) 0.72496(2) 0.07143(19) Uani 1 1 d . . . I6 I 0.32736(3) 0.45145(5) 0.77486(2) 0.07291(19) Uani 1 1 d . . . I3 I 0.17045(3) 0.56184(5) 0.21434(2) 0.0752(2) Uani 1 1 d . . . I4 I -0.02083(3) 1.53589(4) 0.40846(3) 0.0949(3) Uani 1 1 d . . . I1 I 0.52794(3) -0.52080(4) 0.59458(3) 0.0976(3) Uani 1 1 d . . . O2 O 0.1770(2) 0.1873(3) 0.60256(17) 0.0469(11) Uani 1 1 d . . . O3 O 0.2384(2) 0.2767(4) 0.41034(19) 0.0562(13) Uani 1 1 d . . . O1 O 0.4102(2) -0.0856(3) 0.56975(18) 0.0471(12) Uani 1 1 d . . . O6 O 0.2372(3) 0.7186(3) 0.57021(19) 0.0545(13) Uani 1 1 d . . . O5 O 0.3139(2) 0.8210(3) 0.39366(17) 0.0479(12) Uani 1 1 d . . . C7 C 0.3428(3) -0.0639(5) 0.5299(3) 0.0446(17) Uani 1 1 d . . . H7A H 0.3058 -0.1062 0.5352 0.054 Uiso 1 1 calc . . R H7B H 0.3457 -0.0772 0.4944 0.054 Uiso 1 1 calc . . R C26 C 0.1412(4) 0.4140(6) 0.2921(3) 0.057(2) Uani 1 1 d . . . H26 H 0.0938 0.4221 0.2704 0.068 Uiso 1 1 calc . . R C8 C 0.4333(3) -0.1827(5) 0.5728(3) 0.0380(15) Uani 1 1 d . . . O4 O 0.0649(2) 1.0870(3) 0.41891(18) 0.0510(12) Uani 1 1 d . . . C3 C 0.2830(3) 0.1769(5) 0.5797(3) 0.0397(15) Uani 1 1 d . . . C36 C 0.2024(3) 0.8254(5) 0.4100(2) 0.0379(15) Uani 1 1 d . . . C48 C 0.3602(4) 0.7918(5) 0.3671(2) 0.0403(16) Uani 1 1 d . . . C25 C 0.1944(4) 0.4655(5) 0.2808(3) 0.0503(18) Uani 1 1 d . . . C51 C 0.4625(4) 0.7392(5) 0.3210(3) 0.0467(17) Uani 1 1 d . . . C47 C 0.2382(3) 0.7983(5) 0.3689(2) 0.0436(16) Uani 1 1 d . . . H47A H 0.2315 0.7280 0.3598 0.052 Uiso 1 1 calc . . R H47B H 0.2181 0.8372 0.3364 0.052 Uiso 1 1 calc . . R C54 C 0.1675(4) 0.7059(5) 0.5295(3) 0.0519(19) Uani 1 1 d . . . H54A H 0.1293 0.7203 0.5443 0.062 Uiso 1 1 calc . . R H54B H 0.1617 0.6381 0.5158 0.062 Uiso 1 1 calc . . R C49 C 0.3398(4) 0.7453(5) 0.3175(3) 0.0436(16) Uani 1 1 d . . . H49 H 0.2918 0.7319 0.2996 0.052 Uiso 1 1 calc . . R C35 C 0.1755(3) 0.9220(5) 0.4105(3) 0.0405(16) Uani 1 1 d . . . C2 C 0.3052(3) 0.0778(5) 0.5784(3) 0.0392(15) Uani 1 1 d . . . C37 C 0.2012(3) 0.7550(5) 0.4490(2) 0.0382(15) Uani 1 1 d . . . C5 C 0.3045(4) 0.2116(5) 0.4962(3) 0.0428(16) Uani 1 1 d . . . C18 C 0.0405(4) 0.2605(5) 0.6872(3) 0.0486(18) Uani 1 1 d . . . C4 C 0.2810(3) 0.2444(5) 0.5383(3) 0.0379(15) Uani 1 1 d . . . C41 C 0.0486(4) 1.1858(5) 0.4195(3) 0.0414(16) Uani 1 1 d . . . C55 C 0.2537(4) 0.6575(5) 0.6146(3) 0.0463(17) Uani 1 1 d . . . C14 C 0.2536(3) 0.2093(5) 0.6236(3) 0.0421(16) Uani 1 1 d . . . H14A H 0.2761 0.1723 0.6564 0.050 Uiso 1 1 calc . . R H14B H 0.2616 0.2801 0.6310 0.050 Uiso 1 1 calc . . R C52 C 0.4827(4) 0.7865(5) 0.3699(3) 0.0489(18) Uani 1 1 d . . . H52 H 0.5307 0.8015 0.3873 0.059 Uiso 1 1 calc . . R C15 C 0.1358(3) 0.2128(5) 0.6335(2) 0.0382(15) Uani 1 1 d . . . C19 C 0.0160(4) 0.2135(5) 0.6380(3) 0.0497(18) Uani 1 1 d . . . H19 H -0.0323 0.1975 0.6230 0.060 Uiso 1 1 calc . . R C21 C 0.3056(4) 0.2837(5) 0.4523(3) 0.0495(18) Uani 1 1 d . . . H21A H 0.3130 0.3513 0.4663 0.059 Uiso 1 1 calc . . R H21B H 0.3444 0.2670 0.4386 0.059 Uiso 1 1 calc . . R C57 C 0.3448(4) 0.5989(6) 0.6930(3) 0.058(2) Uani 1 1 d . . . H57 H 0.3924 0.5986 0.7150 0.070 Uiso 1 1 calc . . R C23 C 0.2809(4) 0.3927(6) 0.3567(3) 0.070(2) Uani 1 1 d . . . H23 H 0.3282 0.3866 0.3789 0.083 Uiso 1 1 calc . . R C11 C 0.4889(4) -0.3730(5) 0.5853(3) 0.0543(19) Uani 1 1 d . . . C63 C 0.2368(4) 0.6540(5) 0.4510(3) 0.0482(17) Uani 1 1 d . . . H63A H 0.2754 0.6601 0.4359 0.058 Uiso 1 1 calc . . R H63B H 0.2576 0.6337 0.4882 0.058 Uiso 1 1 calc . . R C20 C 0.0634(4) 0.1906(5) 0.6114(3) 0.0488(18) Uani 1 1 d . . . H20 H 0.0467 0.1595 0.5781 0.059 Uiso 1 1 calc . . R C39 C 0.1341(4) 0.8731(5) 0.4847(3) 0.0463(17) Uani 1 1 d . . . C22 C 0.2271(4) 0.3398(5) 0.3673(3) 0.0475(17) Uani 1 1 d . . . C59 C 0.2270(4) 0.5361(6) 0.6721(3) 0.060(2) Uani 1 1 d . . . H59 H 0.1946 0.4940 0.6805 0.072 Uiso 1 1 calc . . R C13 C 0.4065(4) -0.2517(5) 0.5330(3) 0.0471(17) Uani 1 1 d . . . H13 H 0.3699 -0.2344 0.5019 0.057 Uiso 1 1 calc . . R C50 C 0.3919(4) 0.7190(5) 0.2948(3) 0.0488(18) Uani 1 1 d . . . H50 H 0.3785 0.6874 0.2616 0.059 Uiso 1 1 calc . . R C28 C 0.3473(4) 0.0775(6) 0.4457(3) 0.058(2) Uani 1 1 d . . . H28A H 0.3303 0.0102 0.4354 0.070 Uiso 1 1 calc . . R H28B H 0.3265 0.1210 0.4151 0.070 Uiso 1 1 calc . . R C61 C 0.1763(4) 0.9985(5) 0.3684(3) 0.0521(18) Uani 1 1 d . . . H61A H 0.2194 0.9896 0.3587 0.062 Uiso 1 1 calc . . R H61B H 0.1778 1.0649 0.3835 0.062 Uiso 1 1 calc . . R C17 C 0.1120(4) 0.2820(5) 0.7097(3) 0.0487(18) Uani 1 1 d . . . H17 H 0.1283 0.3133 0.7430 0.058 Uiso 1 1 calc . . R C60 C 0.2045(4) 0.5949(6) 0.6258(3) 0.062(2) Uani 1 1 d . . . H60 H 0.1574 0.5920 0.6030 0.074 Uiso 1 1 calc . . R C44 C 0.0079(4) 1.3835(5) 0.4137(3) 0.0516(19) Uani 1 1 d . . . C1 C 0.3243(3) 0.0440(5) 0.5342(3) 0.0409(16) Uani 1 1 d . . . C42 C 0.0799(4) 1.2499(5) 0.4617(3) 0.0497(18) Uani 1 1 d . . . H42 H 0.1147 1.2263 0.4924 0.060 Uiso 1 1 calc . . R C27 C 0.1571(4) 0.3501(6) 0.3352(3) 0.0536(19) Uani 1 1 d . . . H27 H 0.1209 0.3144 0.3426 0.064 Uiso 1 1 calc . . R C46 C -0.0030(4) 1.2219(5) 0.3737(3) 0.0532(19) Uani 1 1 d . . . H46 H -0.0240 1.1792 0.3451 0.064 Uiso 1 1 calc . . R C16 C 0.1600(3) 0.2578(5) 0.6835(3) 0.0455(17) Uani 1 1 d . . . H16 H 0.2085 0.2717 0.6993 0.055 Uiso 1 1 calc . . R C58 C 0.2962(4) 0.5404(5) 0.7048(3) 0.0486(18) Uani 1 1 d . . . C38 C 0.1661(4) 0.7796(5) 0.4855(3) 0.0427(16) Uani 1 1 d . . . C40 C 0.1268(4) 1.0547(5) 0.4592(3) 0.0519(19) Uani 1 1 d . . . H40A H 0.1197 1.0605 0.4938 0.062 Uiso 1 1 calc . . R H40B H 0.1668 1.0972 0.4595 0.062 Uiso 1 1 calc . . R C30 C 0.3094(4) 0.0071(5) 0.6245(3) 0.0503(18) Uani 1 1 d . . . H30A H 0.2691 0.0197 0.6370 0.060 Uiso 1 1 calc . . R H30B H 0.3055 -0.0610 0.6114 0.060 Uiso 1 1 calc . . R C34 C 0.1442(4) 0.9472(5) 0.4501(3) 0.0467(17) Uani 1 1 d . . . C9 C 0.4881(4) -0.2093(6) 0.6192(3) 0.0545(19) Uani 1 1 d . . . H9 H 0.5064 -0.1627 0.6463 0.065 Uiso 1 1 calc . . R C32 C 0.2549(4) 0.3503(5) 0.5390(3) 0.0503(18) Uani 1 1 d . . . H32A H 0.2194 0.3517 0.5573 0.060 Uiso 1 1 calc . . R H32B H 0.2318 0.3724 0.5024 0.060 Uiso 1 1 calc . . R C62 C 0.1115(4) 0.9906(7) 0.3183(3) 0.076(3) Uani 1 1 d . . . H62A H 0.0687 1.0023 0.3273 0.114 Uiso 1 1 calc . . GR H62B H 0.1097 0.9250 0.3032 0.114 Uiso 1 1 calc . . GR H62C H 0.1151 1.0395 0.2926 0.114 Uiso 1 1 calc . . GR C12 C 0.4343(4) -0.3468(5) 0.5394(3) 0.060(2) Uani 1 1 d . . . H12 H 0.4160 -0.3940 0.5125 0.072 Uiso 1 1 calc . . R C6 C 0.3234(3) 0.1119(5) 0.4931(3) 0.0437(16) Uani 1 1 d . . . C43 C 0.0596(4) 1.3493(5) 0.4583(3) 0.059(2) Uani 1 1 d . . . H43 H 0.0813 1.3927 0.4865 0.071 Uiso 1 1 calc . . R C10 C 0.5154(4) -0.3045(6) 0.6248(3) 0.059(2) Uani 1 1 d . . . H10 H 0.5521 -0.3223 0.6558 0.071 Uiso 1 1 calc . . R C24 C 0.2637(4) 0.4548(6) 0.3127(3) 0.067(2) Uani 1 1 d . . . H24 H 0.2997 0.4897 0.3046 0.080 Uiso 1 1 calc . . R C64 C 0.1852(4) 0.5744(5) 0.4208(3) 0.069(2) Uani 1 1 d . . . H64A H 0.1471 0.5675 0.4359 0.103 Uiso 1 1 calc . . GR H64B H 0.2101 0.5120 0.4235 0.103 Uiso 1 1 calc . . GR H64C H 0.1655 0.5932 0.3837 0.103 Uiso 1 1 calc . . GR C33 C 0.3158(4) 0.4229(5) 0.5669(3) 0.068(2) Uani 1 1 d . . . H33A H 0.3516 0.4206 0.5495 0.102 Uiso 1 1 calc . . GR H33B H 0.3367 0.4040 0.6039 0.102 Uiso 1 1 calc . . GR H33C H 0.2969 0.4894 0.5649 0.102 Uiso 1 1 calc . . GR C53 C 0.4313(4) 0.8116(5) 0.3929(3) 0.0484(18) Uani 1 1 d . . . H53 H 0.4451 0.8424 0.4263 0.058 Uiso 1 1 calc . . R C56 C 0.3231(4) 0.6596(6) 0.6479(3) 0.058(2) Uani 1 1 d . . . H56 H 0.3559 0.7019 0.6402 0.070 Uiso 1 1 calc . . R C65 C 0.0857(4) 0.8940(6) 0.5197(3) 0.060(2) Uani 1 1 d . . . H65A H 0.0515 0.9458 0.5027 0.072 Uiso 1 1 calc . . R H65B H 0.0588 0.8340 0.5212 0.072 Uiso 1 1 calc . . R C45 C -0.0230(4) 1.3206(6) 0.3707(3) 0.057(2) Uani 1 1 d . . . H45 H -0.0572 1.3450 0.3399 0.069 Uiso 1 1 calc . . R C31 C 0.3780(4) 0.0176(6) 0.6711(3) 0.073(2) Uani 1 1 d . . . H31A H 0.4181 0.0017 0.6594 0.109 Uiso 1 1 calc . . GR H31B H 0.3770 -0.0273 0.6993 0.109 Uiso 1 1 calc . . GR H31C H 0.3825 0.0850 0.6842 0.109 Uiso 1 1 calc . . GR C66 C 0.1261(4) 0.9256(7) 0.5753(3) 0.077(3) Uani 1 1 d . . . H66A H 0.1567 0.8722 0.5936 0.115 Uiso 1 1 calc . . GR H66B H 0.0931 0.9421 0.5940 0.115 Uiso 1 1 calc . . GR H66C H 0.1547 0.9832 0.5742 0.115 Uiso 1 1 calc . . GR C29 C 0.4267(5) 0.0800(7) 0.4607(4) 0.091(3) Uani 1 1 d . . . H29A H 0.4409 0.0556 0.4314 0.137 Uiso 1 1 calc . . GR H29B H 0.4472 0.0386 0.4917 0.137 Uiso 1 1 calc . . GR H29C H 0.4432 0.1474 0.4689 0.137 Uiso 1 1 calc . . GR 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 I5 0.0654(4) 0.0879(4) 0.0671(4) -0.0118(3) 0.0373(3) 0.0050(3) I2 0.0693(4) 0.0951(5) 0.0605(3) -0.0100(3) 0.0357(3) 0.0080(3) I6 0.0827(4) 0.0866(4) 0.0469(3) 0.0185(3) 0.0175(3) 0.0205(3) I3 0.0866(4) 0.0889(4) 0.0521(3) 0.0190(3) 0.0250(3) 0.0260(3) I4 0.0614(4) 0.0389(3) 0.1726(7) 0.0278(4) 0.0216(4) 0.0138(3) I1 0.0681(4) 0.0412(3) 0.1701(7) 0.0281(4) 0.0200(4) 0.0176(3) O2 0.043(3) 0.054(3) 0.046(3) -0.017(2) 0.018(2) -0.004(2) O3 0.050(3) 0.056(3) 0.058(3) 0.013(3) 0.011(2) -0.007(2) O1 0.048(3) 0.031(2) 0.057(3) -0.008(2) 0.010(2) 0.006(2) O6 0.061(3) 0.049(3) 0.053(3) 0.017(3) 0.017(3) -0.009(2) O5 0.049(3) 0.050(3) 0.048(3) -0.012(2) 0.021(2) -0.001(2) C7 0.050(4) 0.030(3) 0.049(4) 0.000(3) 0.010(3) 0.003(3) C26 0.054(5) 0.063(5) 0.049(5) -0.008(4) 0.011(4) 0.000(4) C8 0.041(4) 0.032(3) 0.041(4) -0.002(3) 0.013(3) 0.002(3) O4 0.054(3) 0.035(3) 0.060(3) -0.002(2) 0.013(2) 0.010(2) C3 0.039(4) 0.034(4) 0.046(4) -0.009(3) 0.014(3) -0.003(3) C36 0.037(4) 0.039(4) 0.036(4) -0.003(3) 0.010(3) 0.004(3) C48 0.055(4) 0.036(4) 0.031(3) 0.003(3) 0.016(3) 0.007(3) C25 0.059(5) 0.051(4) 0.041(4) -0.005(4) 0.018(4) 0.010(4) C51 0.049(4) 0.045(4) 0.052(4) 0.007(4) 0.024(4) 0.006(4) C47 0.038(4) 0.053(4) 0.041(4) 0.000(3) 0.013(3) 0.005(3) C54 0.062(5) 0.042(4) 0.052(4) 0.015(4) 0.018(4) -0.004(4) C49 0.051(4) 0.040(4) 0.042(4) 0.005(3) 0.019(3) 0.002(3) C35 0.045(4) 0.034(4) 0.045(4) 0.003(3) 0.018(3) -0.007(3) C2 0.043(4) 0.031(3) 0.045(4) -0.001(3) 0.016(3) -0.004(3) C37 0.042(4) 0.032(3) 0.039(4) 0.000(3) 0.012(3) 0.006(3) C5 0.050(4) 0.027(3) 0.050(4) 0.009(3) 0.014(3) 0.000(3) C18 0.056(5) 0.042(4) 0.051(4) 0.007(4) 0.022(4) 0.012(4) C4 0.038(4) 0.030(3) 0.049(4) -0.001(3) 0.019(3) 0.007(3) C41 0.047(4) 0.032(4) 0.051(4) 0.002(4) 0.024(3) 0.005(3) C55 0.055(5) 0.039(4) 0.047(4) 0.002(4) 0.019(4) -0.003(4) C14 0.036(4) 0.045(4) 0.044(4) -0.007(3) 0.011(3) 0.002(3) C52 0.049(4) 0.053(4) 0.046(4) -0.007(4) 0.017(3) -0.009(4) C15 0.044(4) 0.034(3) 0.037(4) 0.001(3) 0.014(3) 0.009(3) C19 0.047(4) 0.051(4) 0.052(4) -0.002(4) 0.018(3) 0.000(4) C21 0.058(5) 0.040(4) 0.057(5) 0.008(4) 0.029(4) 0.000(4) C57 0.054(5) 0.067(5) 0.048(4) -0.007(4) 0.009(4) -0.006(4) C23 0.044(4) 0.074(6) 0.092(6) 0.041(5) 0.024(4) 0.011(4) C11 0.050(5) 0.035(4) 0.075(5) 0.012(4) 0.016(4) 0.006(4) C63 0.049(4) 0.034(4) 0.060(5) -0.001(4) 0.017(4) 0.006(3) C20 0.055(5) 0.048(4) 0.043(4) -0.007(4) 0.015(3) 0.003(4) C39 0.056(4) 0.039(4) 0.051(4) 0.000(4) 0.027(4) 0.004(3) C22 0.054(5) 0.040(4) 0.051(4) 0.008(4) 0.020(4) 0.003(4) C59 0.048(5) 0.064(5) 0.072(5) 0.024(5) 0.024(4) 0.004(4) C13 0.045(4) 0.032(4) 0.057(4) 0.001(4) 0.006(3) 0.006(3) C50 0.068(5) 0.041(4) 0.038(4) 0.001(3) 0.018(4) 0.012(4) C28 0.062(5) 0.048(4) 0.066(5) 0.007(4) 0.022(4) 0.004(4) C61 0.062(5) 0.042(4) 0.061(5) 0.009(4) 0.031(4) 0.003(4) C17 0.052(5) 0.053(4) 0.040(4) -0.002(4) 0.013(3) 0.006(4) C60 0.040(4) 0.067(5) 0.072(5) 0.033(5) 0.011(4) 0.003(4) C44 0.041(4) 0.036(4) 0.079(6) 0.006(4) 0.020(4) 0.002(3) C1 0.043(4) 0.033(3) 0.046(4) 0.007(3) 0.012(3) 0.005(3) C42 0.049(4) 0.036(4) 0.057(5) 0.005(4) 0.008(4) 0.008(3) C27 0.048(5) 0.054(5) 0.057(5) -0.008(4) 0.015(4) -0.010(4) C46 0.053(5) 0.048(4) 0.057(5) 0.011(4) 0.016(4) 0.004(4) C16 0.037(4) 0.052(4) 0.043(4) 0.005(4) 0.005(3) 0.005(3) C58 0.058(5) 0.052(4) 0.042(4) 0.004(4) 0.024(4) 0.010(4) C38 0.056(4) 0.030(3) 0.042(4) 0.004(3) 0.016(3) -0.002(3) C40 0.067(5) 0.035(4) 0.053(4) 0.001(4) 0.018(4) 0.010(4) C30 0.063(5) 0.043(4) 0.050(4) 0.003(4) 0.025(4) 0.000(4) C34 0.059(5) 0.030(3) 0.054(4) 0.008(3) 0.022(4) 0.013(3) C9 0.054(5) 0.055(5) 0.048(4) -0.002(4) 0.007(4) 0.004(4) C32 0.054(5) 0.032(4) 0.062(5) -0.003(4) 0.015(4) 0.005(3) C62 0.081(6) 0.081(6) 0.064(5) 0.034(5) 0.019(5) 0.009(5) C12 0.064(5) 0.037(4) 0.074(6) -0.004(4) 0.015(4) 0.000(4) C6 0.042(4) 0.048(4) 0.045(4) 0.002(4) 0.020(3) 0.006(3) C43 0.052(5) 0.039(4) 0.079(6) -0.003(4) 0.009(4) 0.005(4) C10 0.056(5) 0.065(5) 0.050(5) 0.015(4) 0.009(4) 0.012(4) C24 0.057(5) 0.076(6) 0.071(5) 0.034(5) 0.027(4) 0.016(4) C64 0.070(6) 0.040(4) 0.088(6) -0.011(4) 0.015(5) 0.003(4) C33 0.080(6) 0.035(4) 0.081(6) -0.012(4) 0.016(5) 0.002(4) C53 0.046(4) 0.056(5) 0.043(4) -0.011(4) 0.014(3) 0.000(4) C56 0.067(5) 0.058(5) 0.049(5) -0.004(4) 0.018(4) -0.019(4) C65 0.066(5) 0.058(5) 0.054(5) -0.005(4) 0.015(4) -0.003(4) C45 0.047(4) 0.057(5) 0.066(5) 0.028(5) 0.016(4) 0.017(4) C31 0.083(6) 0.069(6) 0.064(5) 0.023(5) 0.020(5) 0.014(5) C66 0.077(6) 0.082(6) 0.064(5) -0.021(5) 0.013(4) -0.013(5) C29 0.072(6) 0.098(7) 0.117(8) 0.024(6) 0.049(6) 0.010(6) _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 I5 C51 2.103(6) . ? I2 C18 2.099(7) . ? I6 C58 2.113(7) . ? I3 C25 2.100(7) . ? I4 C44 2.111(7) . ? I1 C11 2.109(7) . ? O2 C14 1.461(7) . ? O2 C15 1.364(7) . ? O3 C21 1.428(8) . ? O3 C22 1.373(8) . ? O1 C7 1.431(7) . ? O1 C8 1.371(7) . ? O6 C54 1.453(8) . ? O6 C55 1.377(8) . ? O5 C48 1.373(7) . ? O5 C47 1.455(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C1 1.504(8) . ? C26 H26 0.9300 . ? C26 C25 1.366(10) . ? C26 C27 1.373(10) . ? C8 C13 1.368(9) . ? C8 C9 1.391(9) . ? O4 C41 1.363(7) . ? O4 C40 1.400(7) . ? C3 C2 1.401(8) . ? C3 C4 1.407(9) . ? C3 C14 1.514(8) . ? C36 C47 1.514(8) . ? C36 C35 1.400(8) . ? C36 C37 1.399(8) . ? C48 C49 1.384(8) . ? C48 C53 1.371(9) . ? C25 C24 1.361(10) . ? C51 C52 1.372(9) . ? C51 C50 1.367(9) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C54 C38 1.516(9) . ? C49 H49 0.9300 . ? C49 C50 1.388(9) . ? C35 C61 1.514(9) . ? C35 C34 1.410(9) . ? C2 C1 1.408(8) . ? C2 C30 1.520(9) . ? C37 C63 1.517(8) . ? C37 C38 1.392(8) . ? C5 C4 1.403(8) . ? C5 C21 1.512(9) . ? C5 C6 1.396(9) . ? C18 C19 1.378(9) . ? C18 C17 1.372(9) . ? C4 C32 1.510(8) . ? C41 C42 1.382(9) . ? C41 C46 1.389(9) . ? C55 C60 1.383(9) . ? C55 C56 1.365(9) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C52 H52 0.9300 . ? C52 C53 1.379(9) . ? C15 C20 1.389(9) . ? C15 C16 1.385(9) . ? C19 H19 0.9300 . ? C19 C20 1.371(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C57 H57 0.9300 . ? C57 C58 1.349(9) . ? C57 C56 1.389(10) . ? C23 H23 0.9300 . ? C23 C22 1.378(9) . ? C23 C24 1.377(10) . ? C11 C12 1.379(10) . ? C11 C10 1.358(10) . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C63 C64 1.511(9) . ? C20 H20 0.9300 . ? C39 C38 1.400(9) . ? C39 C34 1.405(9) . ? C39 C65 1.551(9) . ? C22 C27 1.372(9) . ? C59 H59 0.9300 . ? C59 C60 1.396(9) . ? C59 C58 1.359(9) . ? C13 H13 0.9300 . ? C13 C12 1.375(9) . ? C50 H50 0.9300 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 C6 1.541(9) . ? C28 C29 1.485(10) . ? C61 H61A 0.9700 . ? C61 H61B 0.9700 . ? C61 C62 1.515(10) . ? C17 H17 0.9300 . ? C17 C16 1.378(9) . ? C60 H60 0.9300 . ? C44 C43 1.361(10) . ? C44 C45 1.385(10) . ? C1 C6 1.408(9) . ? C42 H42 0.9300 . ? C42 C43 1.384(9) . ? C27 H27 0.9300 . ? C46 H46 0.9300 . ? C46 C45 1.374(9) . ? C16 H16 0.9300 . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C40 C34 1.518(8) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C30 C31 1.510(10) . ? C9 H9 0.9300 . ? C9 C10 1.373(10) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C33 1.534(9) . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 0.9600 . ? C12 H12 0.9300 . ? C43 H43 0.9300 . ? C10 H10 0.9300 . ? C24 H24 0.9300 . ? C64 H64A 0.9600 . ? C64 H64B 0.9600 . ? C64 H64C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C53 H53 0.9300 . ? C56 H56 0.9300 . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C65 C66 1.484(9) . ? C45 H45 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C66 H66A 0.9600 . ? C66 H66B 0.9600 . ? C66 H66C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 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 C15 O2 C14 117.6(5) . . ? C22 O3 C21 117.4(5) . . ? C8 O1 C7 116.5(5) . . ? C55 O6 C54 117.7(5) . . ? C48 O5 C47 117.8(5) . . ? O1 C7 H7A 109.8 . . ? O1 C7 H7B 109.8 . . ? O1 C7 C1 109.3(5) . . ? H7A C7 H7B 108.3 . . ? C1 C7 H7A 109.8 . . ? C1 C7 H7B 109.8 . . ? C25 C26 H26 119.7 . . ? C25 C26 C27 120.5(7) . . ? C27 C26 H26 119.7 . . ? O1 C8 C9 116.3(6) . . ? C13 C8 O1 123.9(6) . . ? C13 C8 C9 119.8(6) . . ? C41 O4 C40 116.2(5) . . ? C2 C3 C4 121.3(6) . . ? C2 C3 C14 119.4(6) . . ? C4 C3 C14 119.0(6) . . ? C35 C36 C47 119.6(6) . . ? C37 C36 C47 119.0(6) . . ? C37 C36 C35 121.2(6) . . ? O5 C48 C49 124.7(6) . . ? C53 C48 O5 115.8(6) . . ? C53 C48 C49 119.5(6) . . ? C26 C25 I3 120.7(6) . . ? C24 C25 I3 119.3(6) . . ? C24 C25 C26 120.0(7) . . ? C52 C51 I5 120.9(5) . . ? C50 C51 I5 118.8(5) . . ? C50 C51 C52 120.3(6) . . ? O5 C47 C36 106.0(5) . . ? O5 C47 H47A 110.5 . . ? O5 C47 H47B 110.5 . . ? C36 C47 H47A 110.5 . . ? C36 C47 H47B 110.5 . . ? H47A C47 H47B 108.7 . . ? O6 C54 H54A 110.6 . . ? O6 C54 H54B 110.6 . . ? O6 C54 C38 105.5(5) . . ? H54A C54 H54B 108.8 . . ? C38 C54 H54A 110.6 . . ? C38 C54 H54B 110.6 . . ? C48 C49 H49 120.3 . . ? C48 C49 C50 119.4(6) . . ? C50 C49 H49 120.3 . . ? C36 C35 C61 121.6(6) . . ? C36 C35 C34 119.1(6) . . ? C34 C35 C61 119.3(6) . . ? C3 C2 C1 119.7(6) . . ? C3 C2 C30 120.4(6) . . ? C1 C2 C30 120.0(6) . . ? C36 C37 C63 120.6(6) . . ? C38 C37 C36 118.5(6) . . ? C38 C37 C63 120.9(6) . . ? C4 C5 C21 119.6(6) . . ? C6 C5 C4 120.6(6) . . ? C6 C5 C21 119.8(6) . . ? C19 C18 I2 119.2(5) . . ? C17 C18 I2 120.6(5) . . ? C17 C18 C19 120.1(6) . . ? C3 C4 C32 121.3(6) . . ? C5 C4 C3 118.5(6) . . ? C5 C4 C32 120.2(6) . . ? O4 C41 C42 124.5(6) . . ? O4 C41 C46 116.0(6) . . ? C42 C41 C46 119.5(6) . . ? O6 C55 C60 123.4(6) . . ? C56 C55 O6 116.4(6) . . ? C56 C55 C60 120.1(7) . . ? O2 C14 C3 104.9(5) . . ? O2 C14 H14A 110.8 . . ? O2 C14 H14B 110.8 . . ? C3 C14 H14A 110.8 . . ? C3 C14 H14B 110.8 . . ? H14A C14 H14B 108.9 . . ? C51 C52 H52 120.3 . . ? C51 C52 C53 119.5(7) . . ? C53 C52 H52 120.3 . . ? O2 C15 C20 115.2(6) . . ? O2 C15 C16 125.9(6) . . ? C16 C15 C20 118.9(6) . . ? C18 C19 H19 120.3 . . ? C20 C19 C18 119.4(7) . . ? C20 C19 H19 120.3 . . ? O3 C21 C5 108.1(5) . . ? O3 C21 H21A 110.1 . . ? O3 C21 H21B 110.1 . . ? C5 C21 H21A 110.1 . . ? C5 C21 H21B 110.1 . . ? H21A C21 H21B 108.4 . . ? C58 C57 H57 120.3 . . ? C58 C57 C56 119.4(7) . . ? C56 C57 H57 120.3 . . ? C22 C23 H23 120.5 . . ? C24 C23 H23 120.5 . . ? C24 C23 C22 118.9(7) . . ? C12 C11 I1 119.5(6) . . ? C10 C11 I1 120.6(6) . . ? C10 C11 C12 119.9(7) . . ? C37 C63 H63A 109.1 . . ? C37 C63 H63B 109.1 . . ? H63A C63 H63B 107.8 . . ? C64 C63 C37 112.7(6) . . ? C64 C63 H63A 109.1 . . ? C64 C63 H63B 109.1 . . ? C15 C20 H20 119.4 . . ? C19 C20 C15 121.1(7) . . ? C19 C20 H20 119.4 . . ? C38 C39 C34 118.9(6) . . ? C38 C39 C65 120.9(6) . . ? C34 C39 C65 120.1(6) . . ? O3 C22 C23 123.6(7) . . ? C27 C22 O3 115.7(6) . . ? C27 C22 C23 120.7(7) . . ? C60 C59 H59 120.0 . . ? C58 C59 H59 120.0 . . ? C58 C59 C60 120.0(7) . . ? C8 C13 H13 120.2 . . ? C8 C13 C12 119.5(6) . . ? C12 C13 H13 120.2 . . ? C51 C50 C49 120.4(7) . . ? C51 C50 H50 119.8 . . ? C49 C50 H50 119.8 . . ? H28A C28 H28B 108.1 . . ? C6 C28 H28A 109.6 . . ? C6 C28 H28B 109.6 . . ? C29 C28 H28A 109.6 . . ? C29 C28 H28B 109.6 . . ? C29 C28 C6 110.4(6) . . ? C35 C61 H61A 109.1 . . ? C35 C61 H61B 109.1 . . ? C35 C61 C62 112.7(6) . . ? H61A C61 H61B 107.8 . . ? C62 C61 H61A 109.1 . . ? C62 C61 H61B 109.1 . . ? C18 C17 H17 119.7 . . ? C18 C17 C16 120.7(7) . . ? C16 C17 H17 119.7 . . ? C55 C60 C59 118.7(7) . . ? C55 C60 H60 120.7 . . ? C59 C60 H60 120.7 . . ? C43 C44 I4 119.5(6) . . ? C43 C44 C45 120.7(7) . . ? C45 C44 I4 119.8(5) . . ? C2 C1 C7 120.4(6) . . ? C6 C1 C7 120.4(6) . . ? C6 C1 C2 119.1(6) . . ? C41 C42 H42 120.0 . . ? C41 C42 C43 120.1(7) . . ? C43 C42 H42 120.0 . . ? C26 C27 H27 120.4 . . ? C22 C27 C26 119.2(7) . . ? C22 C27 H27 120.4 . . ? C41 C46 H46 120.0 . . ? C45 C46 C41 120.1(7) . . ? C45 C46 H46 120.0 . . ? C15 C16 H16 120.1 . . ? C17 C16 C15 119.8(6) . . ? C17 C16 H16 120.1 . . ? C57 C58 I6 120.0(6) . . ? C57 C58 C59 121.4(7) . . ? C59 C58 I6 118.6(5) . . ? C37 C38 C54 119.0(6) . . ? C37 C38 C39 121.6(6) . . ? C39 C38 C54 119.3(6) . . ? O4 C40 H40A 109.4 . . ? O4 C40 H40B 109.4 . . ? O4 C40 C34 111.0(5) . . ? H40A C40 H40B 108.0 . . ? C34 C40 H40A 109.4 . . ? C34 C40 H40B 109.4 . . ? C2 C30 H30A 108.9 . . ? C2 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? C31 C30 C2 113.3(6) . . ? C31 C30 H30A 108.9 . . ? C31 C30 H30B 108.9 . . ? C35 C34 C40 121.2(6) . . ? C39 C34 C35 119.9(6) . . ? C39 C34 C40 118.7(6) . . ? C8 C9 H9 120.0 . . ? C10 C9 C8 120.0(7) . . ? C10 C9 H9 120.0 . . ? C4 C32 H32A 109.1 . . ? C4 C32 H32B 109.1 . . ? C4 C32 C33 112.6(6) . . ? H32A C32 H32B 107.8 . . ? C33 C32 H32A 109.1 . . ? C33 C32 H32B 109.1 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62B 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C11 C12 H12 119.7 . . ? C13 C12 C11 120.6(7) . . ? C13 C12 H12 119.7 . . ? C5 C6 C28 119.4(6) . . ? C5 C6 C1 120.7(6) . . ? C1 C6 C28 119.9(6) . . ? C44 C43 C42 119.9(7) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C11 C10 C9 120.3(7) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C25 C24 C23 120.6(7) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64B 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C48 C53 C52 121.0(6) . . ? C48 C53 H53 119.5 . . ? C52 C53 H53 119.5 . . ? C55 C56 C57 120.3(7) . . ? C55 C56 H56 119.9 . . ? C57 C56 H56 119.9 . . ? C39 C65 H65A 108.9 . . ? C39 C65 H65B 108.9 . . ? H65A C65 H65B 107.7 . . ? C66 C65 C39 113.5(7) . . ? C66 C65 H65A 108.9 . . ? C66 C65 H65B 108.9 . . ? C44 C45 H45 120.2 . . ? C46 C45 C44 119.7(7) . . ? C46 C45 H45 120.2 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66B 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I5 C51 C52 C53 -176.9(5) . . . . ? I5 C51 C50 C49 177.8(5) . . . . ? I2 C18 C19 C20 175.5(5) . . . . ? I2 C18 C17 C16 -176.3(5) . . . . ? I3 C25 C24 C23 179.6(6) . . . . ? I4 C44 C43 C42 -178.7(5) . . . . ? I4 C44 C45 C46 178.5(5) . . . . ? I1 C11 C12 C13 178.2(5) . . . . ? I1 C11 C10 C9 -177.9(6) . . . . ? O2 C15 C20 C19 -179.1(6) . . . . ? O2 C15 C16 C17 178.2(6) . . . . ? O3 C22 C27 C26 178.3(6) . . . . ? O1 C7 C1 C2 -70.2(8) . . . . ? O1 C7 C1 C6 112.0(7) . . . . ? O1 C8 C13 C12 178.6(6) . . . . ? O1 C8 C9 C10 -178.5(6) . . . . ? O6 C54 C38 C37 79.3(7) . . . . ? O6 C54 C38 C39 -96.1(7) . . . . ? O6 C55 C60 C59 -179.9(7) . . . . ? O6 C55 C56 C57 -178.8(7) . . . . ? O5 C48 C49 C50 -179.8(6) . . . . ? O5 C48 C53 C52 -179.4(6) . . . . ? C7 O1 C8 C13 17.1(9) . . . . ? C7 O1 C8 C9 -164.2(6) . . . . ? C7 C1 C6 C5 178.4(6) . . . . ? C7 C1 C6 C28 -4.9(9) . . . . ? C26 C25 C24 C23 -0.4(12) . . . . ? C8 O1 C7 C1 177.1(5) . . . . ? C8 C13 C12 C11 -0.3(11) . . . . ? C8 C9 C10 C11 -0.1(12) . . . . ? O4 C41 C42 C43 180.0(6) . . . . ? O4 C41 C46 C45 179.8(6) . . . . ? O4 C40 C34 C35 76.3(8) . . . . ? O4 C40 C34 C39 -108.9(7) . . . . ? C3 C2 C1 C7 -175.3(6) . . . . ? C3 C2 C1 C6 2.5(9) . . . . ? C3 C2 C30 C31 -82.5(8) . . . . ? C3 C4 C32 C33 91.0(8) . . . . ? C36 C35 C61 C62 85.6(8) . . . . ? C36 C35 C34 C39 -6.2(10) . . . . ? C36 C35 C34 C40 168.6(6) . . . . ? C36 C37 C63 C64 -94.3(8) . . . . ? C36 C37 C38 C54 -177.1(6) . . . . ? C36 C37 C38 C39 -1.7(10) . . . . ? C48 O5 C47 C36 172.2(5) . . . . ? C48 C49 C50 C51 -0.4(10) . . . . ? C25 C26 C27 C22 0.9(11) . . . . ? C51 C52 C53 C48 -1.4(10) . . . . ? C47 O5 C48 C49 2.4(9) . . . . ? C47 O5 C48 C53 -177.8(5) . . . . ? C47 C36 C35 C61 4.5(9) . . . . ? C47 C36 C35 C34 -178.1(6) . . . . ? C47 C36 C37 C63 1.5(9) . . . . ? C47 C36 C37 C38 -177.9(6) . . . . ? C54 O6 C55 C60 -8.9(10) . . . . ? C54 O6 C55 C56 169.9(6) . . . . ? C49 C48 C53 C52 0.5(10) . . . . ? C35 C36 C47 O5 90.2(7) . . . . ? C35 C36 C37 C63 -174.2(6) . . . . ? C35 C36 C37 C38 6.4(9) . . . . ? C2 C3 C4 C5 -2.5(9) . . . . ? C2 C3 C4 C32 178.1(6) . . . . ? C2 C3 C14 O2 -87.7(7) . . . . ? C2 C1 C6 C5 0.6(10) . . . . ? C2 C1 C6 C28 177.3(6) . . . . ? C37 C36 C47 O5 -85.6(7) . . . . ? C37 C36 C35 C61 -179.8(6) . . . . ? C37 C36 C35 C34 -2.4(10) . . . . ? C5 C4 C32 C33 -88.3(8) . . . . ? C18 C19 C20 C15 0.8(10) . . . . ? C18 C17 C16 C15 1.1(10) . . . . ? C4 C3 C2 C1 -1.5(9) . . . . ? C4 C3 C2 C30 177.9(6) . . . . ? C4 C3 C14 O2 86.2(7) . . . . ? C4 C5 C21 O3 -91.2(7) . . . . ? C4 C5 C6 C28 178.5(6) . . . . ? C4 C5 C6 C1 -4.8(10) . . . . ? C41 O4 C40 C34 -172.8(5) . . . . ? C41 C42 C43 C44 1.0(11) . . . . ? C41 C46 C45 C44 -0.7(11) . . . . ? C55 O6 C54 C38 -177.9(6) . . . . ? C14 O2 C15 C20 179.8(5) . . . . ? C14 O2 C15 C16 -0.2(9) . . . . ? C14 C3 C2 C1 172.2(6) . . . . ? C14 C3 C2 C30 -8.3(9) . . . . ? C14 C3 C4 C5 -176.3(6) . . . . ? C14 C3 C4 C32 4.4(9) . . . . ? C52 C51 C50 C49 -0.5(10) . . . . ? C15 O2 C14 C3 -177.6(5) . . . . ? C19 C18 C17 C16 0.5(10) . . . . ? C21 O3 C22 C23 14.6(10) . . . . ? C21 O3 C22 C27 -163.5(6) . . . . ? C21 C5 C4 C3 -177.7(6) . . . . ? C21 C5 C4 C32 1.6(9) . . . . ? C21 C5 C6 C28 1.8(10) . . . . ? C21 C5 C6 C1 178.6(6) . . . . ? C23 C22 C27 C26 0.2(11) . . . . ? C63 C37 C38 C54 3.5(9) . . . . ? C63 C37 C38 C39 178.8(6) . . . . ? C20 C15 C16 C17 -1.7(10) . . . . ? C22 O3 C21 C5 177.2(6) . . . . ? C22 C23 C24 C25 1.5(13) . . . . ? C13 C8 C9 C10 0.2(11) . . . . ? C50 C51 C52 C53 1.4(10) . . . . ? C61 C35 C34 C39 171.2(6) . . . . ? C61 C35 C34 C40 -14.0(10) . . . . ? C17 C18 C19 C20 -1.4(10) . . . . ? C60 C55 C56 C57 0.1(11) . . . . ? C60 C59 C58 I6 179.2(6) . . . . ? C60 C59 C58 C57 -1.7(12) . . . . ? C1 C2 C30 C31 96.9(8) . . . . ? C42 C41 C46 C45 -0.5(10) . . . . ? C27 C26 C25 I3 179.2(5) . . . . ? C27 C26 C25 C24 -0.8(11) . . . . ? C46 C41 C42 C43 0.3(10) . . . . ? C16 C15 C20 C19 0.8(10) . . . . ? C58 C57 C56 C55 -2.3(11) . . . . ? C58 C59 C60 C55 -0.6(12) . . . . ? C38 C37 C63 C64 85.1(8) . . . . ? C38 C39 C34 C35 10.7(10) . . . . ? C38 C39 C34 C40 -164.2(6) . . . . ? C38 C39 C65 C66 85.6(9) . . . . ? C40 O4 C41 C42 -12.9(9) . . . . ? C40 O4 C41 C46 166.8(6) . . . . ? C30 C2 C1 C7 5.3(9) . . . . ? C30 C2 C1 C6 -176.9(6) . . . . ? C34 C35 C61 C62 -91.7(8) . . . . ? C34 C39 C38 C54 168.6(6) . . . . ? C34 C39 C38 C37 -6.7(10) . . . . ? C34 C39 C65 C66 -96.9(8) . . . . ? C9 C8 C13 C12 0.0(10) . . . . ? C12 C11 C10 C9 -0.2(12) . . . . ? C6 C5 C4 C3 5.7(10) . . . . ? C6 C5 C4 C32 -175.0(6) . . . . ? C6 C5 C21 O3 85.5(8) . . . . ? C43 C44 C45 C46 2.0(11) . . . . ? C10 C11 C12 C13 0.4(12) . . . . ? C24 C23 C22 O3 -179.3(7) . . . . ? C24 C23 C22 C27 -1.4(12) . . . . ? C53 C48 C49 C50 0.4(9) . . . . ? C56 C55 C60 C59 1.3(11) . . . . ? C56 C57 C58 I6 -177.8(5) . . . . ? C56 C57 C58 C59 3.1(11) . . . . ? C65 C39 C38 C54 -13.8(10) . . . . ? C65 C39 C38 C37 170.8(6) . . . . ? C65 C39 C34 C35 -166.9(6) . . . . ? C65 C39 C34 C40 18.2(10) . . . . ? C45 C44 C43 C42 -2.2(12) . . . . ? C29 C28 C6 C5 94.9(8) . . . . ? C29 C28 C6 C1 -81.9(8) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962421' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_I-gf-298K _audit_creation_date 2013-12-25 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'I-gf, 298 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-iodophenoxy)methylbenzene ; _chemical_formula_moiety 'C33 H33 I3 O3' _chemical_formula_sum 'C33 H33 I3 O3' _chemical_formula_weight 858.29 _chemical_melting_point ? 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9304(5) _cell_length_b 13.4111(6) _cell_length_c 24.9283(15) _cell_angle_alpha 90.00 _cell_angle_beta 93.303(5) _cell_angle_gamma 90.00 _cell_volume 3314.4(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2737 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.1262 _cell_measurement_theta_min 3.6027 _exptl_absorpt_coefficient_mu 2.859 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.56901 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1656 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.07 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_unetI/netI 0.0477 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 16131 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.19 _diffrn_reflns_theta_min 3.61 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.839 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0565442000 _diffrn_orient_matrix_UB_12 -0.0204326000 _diffrn_orient_matrix_UB_13 -0.0122690000 _diffrn_orient_matrix_UB_21 0.0409951000 _diffrn_orient_matrix_UB_22 0.0101031000 _diffrn_orient_matrix_UB_23 0.0236144000 _diffrn_orient_matrix_UB_31 -0.0154519000 _diffrn_orient_matrix_UB_32 -0.0476971000 _diffrn_orient_matrix_UB_33 0.0102562000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4145 _reflns_number_total 7532 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.828 _refine_diff_density_min -0.951 _refine_diff_density_rms 0.073 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 405 _refine_ls_number_reflns 7532 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0471 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+3.9177P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0962 _refine_ls_wR_factor_ref 0.1198 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C22B-C21B \\sim C23B-C22B \\sim C24B-C23B \\sim C25B-C24B \\sim C26B-C25B \\sim C26B-C21B with sigma of 0.02 C22A-C21A \\sim C23A-C22A \\sim C24A-C23A \\sim C25A-C24A \\sim C26A-C25A \\sim C26A-C21A with sigma of 0.02 3. Others Fixed Sof: I3A(0.5) C23A(0.5) H23A(0.5) C22A(0.5) H22A(0.5) C21A(0.5) C25A(0.5) H25A(0.5) O3B(0.5) O2B(0.5) C5B(0.5) C24A(0.5) C26A(0.5) H26A(0.5) C27B(0.5) H27A(0.5) H27B(0.5) C20B(0.5) H20A(0.5) H20B(0.5) C3B(0.5) C4A(0.5) C9B(0.5) H9BA(0.5) H9BB(0.5) C10A(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C10B(0.5) H10D(0.5) H10E(0.5) H10F(0.5) C9A(0.5) H9AA(0.5) H9AB(0.5) C4B(0.5) C5A(0.5) C3A(0.5) C27A(0.5) H27C(0.5) H27D(0.5) O2A(0.5) C20A(0.5) H20C(0.5) H20D(0.5) O3A(0.5) C21B(0.5) C26B(0.5) H26B(0.5) C25B(0.5) H25B(0.5) C24B(0.5) C23B(0.5) H23B(0.5) C22B(0.5) H22B(0.5) I3B(0.5) 4.a Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C13(H13A,H13B), C27B(H27A,H27B), C20B(H20A,H20B), C7(H7A,H7B), C9B(H9BA,H9BB), C9A(H9AA,H9AB), C27A(H27C,H27D), C20A(H20C,H20D) 4.b Aromatic/amide H refined with riding coordinates: C19(H19), C23A(H23A), C22A(H22A), C25A(H25A), C33(H33), C18(H18), C15(H15), C16(H16), C29(H29), C26A(H26A), C30(H30), C32(H32), C26B(H26B), C25B(H25B), C23B(H23B), C22B(H22B) 4.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C8(H8A,H8B,H8C), C10A(H10A,H10B,H10C), C10B(H10D,H10E, H10F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn I3A I 0.0534(6) -0.0223(4) 0.6011(3) 0.1263(18) Uani 0.50 1 d A 2 . I1 I 1.28966(4) 0.80538(4) 0.719076(19) 0.09384(18) Uani 1 1 d . . . I2 I 0.37750(5) 1.05552(4) 0.220316(18) 0.09833(19) Uani 1 1 d . . . O1 O 0.7407(4) 0.6846(3) 0.60474(14) 0.0648(9) Uani 1 1 d . . . C14 C 0.8570(5) 0.7110(3) 0.6330(2) 0.0516(12) Uani 1 1 d . . . C6 C 0.4656(5) 0.7443(3) 0.5454(2) 0.0595(13) Uani 1 1 d . . . C19 C 0.8625(5) 0.7569(4) 0.6829(2) 0.0566(13) Uani 1 1 d . . . H19 H 0.7836 0.7712 0.6997 0.068 Uiso 1 1 calc . . R C23A C 0.0877(17) 0.1999(10) 0.6323(6) 0.070(5) Uiso 0.50 1 d A 2 . H23A H 0.0416 0.1841 0.6626 0.084 Uiso 0.50 1 calc A 2 R C22A C 0.134(3) 0.2927(15) 0.6253(10) 0.072(9) Uiso 0.50 1 d A 2 . H22A H 0.1296 0.3397 0.6526 0.086 Uiso 0.50 1 calc A 2 R C21A C 0.188(2) 0.3174(14) 0.5788(7) 0.050(7) Uiso 0.50 1 d A 2 . C25A C 0.1752(11) 0.1520(8) 0.5492(5) 0.051(3) Uiso 0.50 1 d A 2 . H25A H 0.1894 0.1027 0.5239 0.061 Uiso 0.50 1 calc A 2 R O3B O 0.2490(11) 0.4110(7) 0.5719(4) 0.057(3) Uiso 0.50 1 d B 1 . C33 C 0.2896(6) 0.8983(5) 0.3653(3) 0.091(2) Uani 1 1 d . . . H33 H 0.2183 0.8960 0.3879 0.109 Uiso 1 1 calc . . R C18 C 0.9863(6) 0.7814(4) 0.7072(2) 0.0612(13) Uani 1 1 d . . . H18 H 0.9907 0.8125 0.7406 0.073 Uiso 1 1 calc . . R C28 C 0.4026(7) 0.8407(4) 0.3759(3) 0.0748(17) Uani 1 1 d . . . C11 C 0.5253(6) 0.8481(3) 0.5444(2) 0.0659(14) Uani 1 1 d . . . H11A H 0.6159 0.8465 0.5612 0.079 Uiso 1 1 calc . . R H11B H 0.5318 0.8690 0.5074 0.079 Uiso 1 1 calc . . R C17 C 1.1037(5) 0.7600(4) 0.6825(2) 0.0594(13) Uani 1 1 d . . . C13 C 0.6139(5) 0.7058(4) 0.6276(2) 0.0599(13) Uani 1 1 d . . . H13A H 0.6069 0.7762 0.6359 0.072 Uiso 1 1 calc B . R H13B H 0.6053 0.6678 0.6603 0.072 Uiso 1 1 calc . . R C15 C 0.9759(6) 0.6903(4) 0.6089(2) 0.0640(14) Uani 1 1 d . . . H15 H 0.9724 0.6594 0.5755 0.077 Uiso 1 1 calc . . R C1 C 0.5060(5) 0.6757(4) 0.5854(2) 0.0566(13) Uani 1 1 d . . . O2B O 0.4311(10) 0.7761(7) 0.4115(5) 0.069(4) Uiso 0.50 1 d B 1 . C16 C 1.0987(6) 0.7145(4) 0.6334(2) 0.0660(14) Uani 1 1 d . . . H16 H 1.1778 0.7001 0.6167 0.079 Uiso 1 1 calc . . R C2 C 0.4571(5) 0.5771(3) 0.5843(2) 0.0606(13) Uani 1 1 d . . . C29 C 0.5092(7) 0.8458(5) 0.3443(3) 0.0862(19) Uani 1 1 d B . . H29 H 0.5861 0.8080 0.3526 0.103 Uiso 1 1 calc . . R C5B C 0.3916(14) 0.7091(12) 0.5011(9) 0.049(4) Uani 0.50 1 d B 1 . C12 C 0.4421(7) 0.9235(4) 0.5733(3) 0.092(2) Uani 1 1 d . . . H12A H 0.3511 0.9227 0.5581 0.137 Uiso 1 1 calc B . GR H12B H 0.4798 0.9888 0.5693 0.137 Uiso 1 1 calc . . GR H12C H 0.4427 0.9067 0.6107 0.137 Uiso 1 1 calc . . GR C24A C 0.1084(12) 0.1294(10) 0.5948(5) 0.053(4) Uiso 0.50 1 d A 2 . C26A C 0.2210(14) 0.2480(9) 0.5413(6) 0.052(4) Uiso 0.50 1 d A 2 . H26A H 0.2713 0.2646 0.5122 0.062 Uiso 0.50 1 calc A 2 R C27B C 0.3420(17) 0.7818(11) 0.4525(7) 0.055(4) Uiso 0.50 1 d B 1 . H27A H 0.2524 0.7625 0.4389 0.066 Uiso 0.50 1 calc B 1 R H27B H 0.3379 0.8499 0.4655 0.066 Uiso 0.50 1 calc B 1 R C30 C 0.5030(7) 0.9065(5) 0.3004(3) 0.0833(18) Uani 1 1 d . . . H30 H 0.5759 0.9099 0.2787 0.100 Uiso 1 1 calc B . R C32 C 0.2835(7) 0.9594(5) 0.3208(3) 0.091(2) Uani 1 1 d . . . H32 H 0.2074 0.9983 0.3129 0.109 Uiso 1 1 calc B . R C20B C 0.3453(12) 0.4351(8) 0.5315(4) 0.048(3) Uiso 0.50 1 d B 1 . H20A H 0.3055 0.4206 0.4959 0.057 Uiso 0.50 1 calc B 1 R H20B H 0.4255 0.3944 0.5373 0.057 Uiso 0.50 1 calc B 1 R C31 C 0.3899(6) 0.9626(4) 0.2881(2) 0.0717(15) Uani 1 1 d B . . C3B C 0.383(2) 0.5428(17) 0.5350(10) 0.050(4) Uani 0.50 1 d B 1 . C4A C 0.2875(13) 0.6276(9) 0.5152(5) 0.057(3) Uani 0.50 1 d A 2 . C7 C 0.4985(6) 0.5046(4) 0.6288(2) 0.0725(16) Uani 1 1 d B . . H7A H 0.4909 0.4372 0.6148 0.087 Uiso 1 1 calc . . R H7B H 0.5924 0.5161 0.6399 0.087 Uiso 1 1 calc . . R C8 C 0.4152(8) 0.5130(5) 0.6771(3) 0.102(2) Uani 1 1 d . . . H8A H 0.3226 0.4987 0.6668 0.153 Uiso 1 1 calc B . GR H8B H 0.4223 0.5795 0.6913 0.153 Uiso 1 1 calc . . GR H8C H 0.4476 0.4663 0.7040 0.153 Uiso 1 1 calc . . GR C9B C 0.2509(12) 0.5799(9) 0.4488(5) 0.055(3) Uani 0.50 1 d B 1 . H9BA H 0.2745 0.5129 0.4381 0.066 Uiso 0.50 1 calc B 1 R H9BB H 0.2635 0.6238 0.4186 0.066 Uiso 0.50 1 calc B 1 R C10A C 0.180(2) 0.5710(13) 0.4255(7) 0.098(5) Uani 0.50 1 d A 2 . H10A H 0.2204 0.6248 0.4067 0.146 Uiso 0.50 1 calc A 2 GR H10B H 0.0959 0.5531 0.4073 0.146 Uiso 0.50 1 calc A 2 GR H10C H 0.2397 0.5145 0.4266 0.146 Uiso 0.50 1 calc A 2 GR C10B C 0.1019(16) 0.5815(16) 0.4617(8) 0.090(6) Uani 0.50 1 d B 1 . H10D H 0.0472 0.5629 0.4303 0.135 Uiso 0.50 1 calc B 1 GR H10E H 0.0777 0.6475 0.4727 0.135 Uiso 0.50 1 calc B 1 GR H10F H 0.0874 0.5353 0.4902 0.135 Uiso 0.50 1 calc B 1 GR C9A C 0.1563(18) 0.6033(12) 0.4818(7) 0.077(4) Uani 0.50 1 d A 2 . H9AA H 0.1087 0.5507 0.4996 0.092 Uiso 0.50 1 calc A 2 R H9AB H 0.0989 0.6619 0.4804 0.092 Uiso 0.50 1 calc A 2 R C4B C 0.3443(11) 0.6111(8) 0.4947(5) 0.041(3) Uani 0.50 1 d B 1 . C5A C 0.3444(14) 0.7221(13) 0.5108(8) 0.049(4) Uani 0.50 1 d A 2 . C3A C 0.346(2) 0.5560(16) 0.5500(10) 0.056(5) Uani 0.50 1 d A 2 . C27A C 0.3076(14) 0.7916(8) 0.4691(5) 0.053(3) Uani 0.50 1 d A 2 . H27C H 0.3090 0.8591 0.4831 0.064 Uiso 0.50 1 calc A 2 R H27D H 0.2177 0.7773 0.4538 0.064 Uiso 0.50 1 calc A 2 R O2A O 0.4086(13) 0.7802(7) 0.4278(5) 0.068(3) Uiso 0.50 1 d A 2 . C20A C 0.2981(14) 0.4455(9) 0.5406(6) 0.065(4) Uiso 0.50 1 d A 2 . H20C H 0.2497 0.4400 0.5058 0.078 Uiso 0.50 1 calc A 2 R H20D H 0.3759 0.4018 0.5408 0.078 Uiso 0.50 1 calc A 2 R O3A O 0.2168(11) 0.4172(8) 0.5796(4) 0.067(4) Uiso 0.50 1 d A 2 . C21B C 0.203(2) 0.3140(15) 0.5742(7) 0.055(7) Uiso 0.50 1 d B 1 . C26B C 0.1999(15) 0.2512(9) 0.5298(6) 0.057(5) Uiso 0.50 1 d B 1 . H26B H 0.2287 0.2758 0.4975 0.069 Uiso 0.50 1 calc B 1 R C25B C 0.1556(12) 0.1528(8) 0.5318(5) 0.054(4) Uiso 0.50 1 d B 1 . H25B H 0.1617 0.1110 0.5022 0.065 Uiso 0.50 1 calc B 1 R C24B C 0.1025(12) 0.1185(9) 0.5781(5) 0.049(3) Uiso 0.50 1 d B 1 . C23B C 0.0910(16) 0.1798(10) 0.6227(6) 0.058(4) Uiso 0.50 1 d B 1 . H23B H 0.0562 0.1555 0.6540 0.070 Uiso 0.50 1 calc B 1 R C22B C 0.134(2) 0.2806(13) 0.6190(9) 0.067(9) Uiso 0.50 1 d B 1 . H22B H 0.1164 0.3252 0.6463 0.081 Uiso 0.50 1 calc B 1 R I3B I 0.0364(7) -0.0280(4) 0.5880(3) 0.1022(10) Uani 0.50 1 d B 1 . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I3A 0.0830(15) 0.0577(17) 0.243(5) 0.056(2) 0.052(3) -0.0015(13) I1 0.0699(3) 0.1197(4) 0.0894(3) -0.0107(3) -0.0176(2) -0.0137(3) I2 0.1020(4) 0.1190(4) 0.0734(3) 0.0131(3) -0.0007(2) -0.0207(3) O1 0.060(2) 0.073(2) 0.061(2) -0.0179(19) -0.0029(17) -0.0065(18) C14 0.057(3) 0.048(3) 0.049(3) 0.001(2) -0.002(2) -0.010(2) C6 0.065(3) 0.042(3) 0.070(4) 0.000(3) -0.007(3) -0.009(2) C19 0.064(3) 0.055(3) 0.052(3) -0.005(3) 0.005(3) -0.007(2) C33 0.065(4) 0.093(4) 0.115(6) 0.046(4) 0.002(4) 0.006(3) C18 0.075(4) 0.061(3) 0.047(3) -0.005(3) -0.005(3) -0.009(3) C28 0.076(4) 0.056(3) 0.089(5) 0.017(3) -0.020(4) 0.001(3) C11 0.070(4) 0.047(3) 0.081(4) 0.000(3) 0.006(3) -0.010(3) C17 0.059(3) 0.058(3) 0.060(4) 0.008(3) -0.007(3) -0.010(3) C13 0.058(3) 0.062(3) 0.059(3) -0.003(3) 0.001(2) -0.005(3) C15 0.067(4) 0.065(3) 0.060(3) -0.014(3) 0.006(3) -0.004(3) C1 0.058(3) 0.052(3) 0.059(3) 0.003(3) -0.005(2) -0.006(2) C16 0.057(3) 0.077(4) 0.064(4) 0.001(3) 0.005(3) -0.005(3) C2 0.064(3) 0.044(3) 0.073(4) 0.009(3) -0.009(3) -0.001(2) C29 0.087(5) 0.077(4) 0.092(5) -0.014(4) -0.015(4) 0.028(4) C5B 0.027(8) 0.037(6) 0.084(10) 0.016(6) 0.010(7) 0.013(6) C12 0.111(5) 0.055(3) 0.111(5) -0.008(3) 0.027(4) -0.003(3) C30 0.074(4) 0.094(5) 0.082(5) -0.028(4) 0.007(3) 0.006(4) C32 0.063(4) 0.096(5) 0.111(5) 0.044(4) -0.002(4) 0.004(3) C31 0.073(4) 0.070(4) 0.071(4) -0.002(3) -0.004(3) -0.008(3) C3B 0.055(11) 0.039(7) 0.056(12) -0.007(7) 0.009(7) 0.001(7) C4A 0.053(8) 0.054(7) 0.065(9) 0.003(6) -0.004(6) -0.010(6) C7 0.080(4) 0.057(3) 0.079(4) 0.017(3) -0.014(3) 0.002(3) C8 0.118(6) 0.102(5) 0.086(5) 0.034(4) 0.004(4) -0.002(4) C9B 0.054(7) 0.055(6) 0.054(8) -0.006(6) -0.008(6) -0.008(6) C10A 0.112(15) 0.095(10) 0.085(12) -0.033(9) 0.003(11) -0.008(10) C10B 0.054(10) 0.135(15) 0.079(13) 0.018(11) -0.010(8) -0.006(9) C9A 0.077(12) 0.064(8) 0.088(13) -0.002(8) -0.019(9) 0.012(8) C4B 0.036(6) 0.042(5) 0.047(7) 0.005(5) 0.008(5) -0.002(4) C5A 0.027(8) 0.041(7) 0.078(11) 0.004(6) -0.014(7) 0.010(6) C3A 0.066(13) 0.036(8) 0.067(15) 0.006(8) 0.003(8) -0.001(7) C27A 0.065(8) 0.049(6) 0.047(8) 0.007(5) 0.015(6) 0.009(5) I3B 0.101(2) 0.0589(11) 0.1487(15) 0.0127(9) 0.0284(12) -0.0258(11) _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 I3A C24A 2.114(14) . ? I1 C17 2.101(5) . ? I2 C31 2.098(6) . ? O1 C14 1.365(6) . ? O1 C13 1.440(6) . ? C14 C19 1.387(7) . ? C14 C15 1.382(7) . ? C6 C11 1.514(6) . ? C6 C1 1.399(7) . ? C6 C5B 1.37(2) . ? C6 C5A 1.470(18) . ? C19 H19 0.9300 . ? C19 C18 1.379(7) . ? C23A H23A 0.9300 . ? C23A C22A 1.343(14) . ? C23A C24A 1.353(14) . ? C22A H22A 0.9300 . ? C22A C21A 1.345(14) . ? C21A C26A 1.372(13) . ? C21A O3A 1.37(2) . ? C25A H25A 0.9300 . ? C25A C24A 1.382(12) . ? C25A C26A 1.384(12) . ? O3B C20B 1.465(16) . ? O3B C21B 1.38(2) . ? C33 H33 0.9300 . ? C33 C28 1.375(8) . ? C33 C32 1.379(8) . ? C18 H18 0.9300 . ? C18 C17 1.379(7) . ? C28 O2B 1.261(11) . ? C28 C29 1.357(9) . ? C28 O2A 1.525(13) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.513(8) . ? C17 C16 1.368(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C1 1.512(7) . ? C15 H15 0.9300 . ? C15 C16 1.371(7) . ? C1 C2 1.409(7) . ? O2B C27B 1.392(19) . ? C16 H16 0.9300 . ? C2 C3B 1.47(3) . ? C2 C7 1.513(7) . ? C2 C3A 1.39(3) . ? C29 H29 0.9300 . ? C29 C30 1.363(9) . ? C5B C27B 1.61(2) . ? C5B C4B 1.40(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C26A H26A 0.9300 . ? C27B H27A 0.9700 . ? C27B H27B 0.9700 . ? C30 H30 0.9300 . ? C30 C31 1.372(8) . ? C32 H32 0.9300 . ? C32 C31 1.371(8) . ? C20B H20A 0.9700 . ? C20B H20B 0.9700 . ? C20B C3B 1.49(3) . ? C3B C4B 1.40(3) . ? C4A C9A 1.541(19) . ? C4A C5A 1.39(2) . ? C4A C3A 1.40(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.505(9) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9B H9BA 0.9700 . ? C9B H9BB 0.9700 . ? C9B C10B 1.53(2) . ? C9B C4B 1.491(16) . ? C10A H10A 0.9600 . ? C10A H10B 0.9600 . ? C10A H10C 0.9600 . ? C10A C9A 1.50(2) . ? C10B H10D 0.9600 . ? C10B H10E 0.9600 . ? C10B H10F 0.9600 . ? C9A H9AA 0.9700 . ? C9A H9AB 0.9700 . ? C5A C27A 1.43(2) . ? C3A C20A 1.57(3) . ? C27A H27C 0.9700 . ? C27A H27D 0.9700 . ? C27A O2A 1.487(17) . ? C20A H20C 0.9700 . ? C20A H20D 0.9700 . ? C20A O3A 1.352(18) . ? C21B C26B 1.389(13) . ? C21B C22B 1.417(14) . ? C26B H26B 0.9300 . ? C26B C25B 1.392(12) . ? C25B H25B 0.9300 . ? C25B C24B 1.377(12) . ? C24B C23B 1.392(14) . ? C24B I3B 2.090(13) . ? C23B H23B 0.9300 . ? C23B C22B 1.422(14) . ? C22B H22B 0.9300 . ? 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 C14 O1 C13 118.6(4) . . ? O1 C14 C19 124.5(5) . . ? O1 C14 C15 116.3(4) . . ? C15 C14 C19 119.2(5) . . ? C1 C6 C11 121.3(5) . . ? C1 C6 C5A 118.4(8) . . ? C5B C6 C11 119.7(9) . . ? C5B C6 C1 117.7(8) . . ? C5B C6 C5A 22.7(7) . . ? C5A C6 C11 119.1(8) . . ? C14 C19 H19 120.4 . . ? C18 C19 C14 119.2(5) . . ? C18 C19 H19 120.4 . . ? C22A C23A H23A 120.3 . . ? C22A C23A C24A 119.5(17) . . ? C24A C23A H23A 120.3 . . ? C23A C22A H22A 120.2 . . ? C23A C22A C21A 120(2) . . ? C21A C22A H22A 120.2 . . ? C22A C21A C26A 122.9(19) . . ? C22A C21A O3A 108.7(13) . . ? O3A C21A C26A 127.9(15) . . ? C24A C25A H25A 120.0 . . ? C24A C25A C26A 120.0(12) . . ? C26A C25A H25A 120.0 . . ? C21B O3B C20B 117.9(10) . . ? C28 C33 H33 120.5 . . ? C28 C33 C32 119.0(6) . . ? C32 C33 H33 120.5 . . ? C19 C18 H18 119.7 . . ? C19 C18 C17 120.6(5) . . ? C17 C18 H18 119.7 . . ? C33 C28 O2A 116.9(7) . . ? O2B C28 C33 131.9(8) . . ? O2B C28 C29 107.0(7) . . ? O2B C28 O2A 16.5(7) . . ? C29 C28 C33 121.1(6) . . ? C29 C28 O2A 121.6(8) . . ? C6 C11 H11A 109.1 . . ? C6 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C12 C11 C6 112.4(5) . . ? C12 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C18 C17 I1 119.4(4) . . ? C16 C17 I1 120.2(4) . . ? C16 C17 C18 120.3(5) . . ? O1 C13 H13A 110.6 . . ? O1 C13 H13B 110.6 . . ? O1 C13 C1 105.8(4) . . ? H13A C13 H13B 108.7 . . ? C1 C13 H13A 110.6 . . ? C1 C13 H13B 110.6 . . ? C14 C15 H15 119.3 . . ? C16 C15 C14 121.3(5) . . ? C16 C15 H15 119.3 . . ? C6 C1 C13 118.9(4) . . ? C6 C1 C2 121.3(5) . . ? C2 C1 C13 119.6(5) . . ? C28 O2B C27B 110.7(10) . . ? C17 C16 C15 119.3(5) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C1 C2 C3B 117.7(11) . . ? C1 C2 C7 120.7(5) . . ? C3B C2 C7 120.9(10) . . ? C3A C2 C1 117.7(10) . . ? C3A C2 C3B 22.7(8) . . ? C3A C2 C7 119.6(11) . . ? C28 C29 H29 120.2 . . ? C28 C29 C30 119.7(6) . . ? C30 C29 H29 120.2 . . ? C6 C5B C27B 121.5(13) . . ? C6 C5B C4B 125.0(15) . . ? C4B C5B C27B 113.3(16) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C23A C24A I3A 124.8(9) . . ? C23A C24A C25A 120.9(12) . . ? C25A C24A I3A 114.3(9) . . ? C21A C26A C25A 116.0(13) . . ? C21A C26A H26A 122.0 . . ? C25A C26A H26A 122.0 . . ? O2B C27B C5B 109.9(12) . . ? O2B C27B H27A 109.7 . . ? O2B C27B H27B 109.7 . . ? C5B C27B H27A 109.7 . . ? C5B C27B H27B 109.7 . . ? H27A C27B H27B 108.2 . . ? C29 C30 H30 119.8 . . ? C29 C30 C31 120.4(6) . . ? C31 C30 H30 119.8 . . ? C33 C32 H32 120.1 . . ? C31 C32 C33 119.8(6) . . ? C31 C32 H32 120.1 . . ? O3B C20B H20A 109.6 . . ? O3B C20B H20B 109.6 . . ? O3B C20B C3B 110.2(10) . . ? H20A C20B H20B 108.1 . . ? C3B C20B H20A 109.6 . . ? C3B C20B H20B 109.6 . . ? C30 C31 I2 121.0(5) . . ? C32 C31 I2 119.1(5) . . ? C32 C31 C30 119.9(6) . . ? C2 C3B C20B 117.6(19) . . ? C4B C3B C2 120.0(17) . . ? C4B C3B C20B 122(2) . . ? C5A C4A C9A 118.9(13) . . ? C5A C4A C3A 121.2(16) . . ? C3A C4A C9A 119.9(15) . . ? C2 C7 H7A 108.9 . . ? C2 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C8 C7 C2 113.6(5) . . ? C8 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? H9BA C9B H9BB 107.7 . . ? C10B C9B H9BA 108.8 . . ? C10B C9B H9BB 108.8 . . ? C4B C9B H9BA 108.8 . . ? C4B C9B H9BB 108.8 . . ? C4B C9B C10B 113.6(14) . . ? H10A C10A H10B 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C9A C10A H10A 109.5 . . ? C9A C10A H10B 109.5 . . ? C9A C10A H10C 109.5 . . ? C4A C9A H9AA 109.0 . . ? C4A C9A H9AB 109.0 . . ? C10A C9A C4A 113.1(17) . . ? C10A C9A H9AA 109.0 . . ? C10A C9A H9AB 109.0 . . ? H9AA C9A H9AB 107.8 . . ? C5B C4B C9B 122.7(13) . . ? C3B C4B C5B 117.2(16) . . ? C3B C4B C9B 120.0(14) . . ? C4A C5A C6 117.4(14) . . ? C4A C5A C27A 124.2(15) . . ? C27A C5A C6 117.5(13) . . ? C2 C3A C4A 122.0(18) . . ? C2 C3A C20A 120.5(18) . . ? C4A C3A C20A 116(2) . . ? C5A C27A H27C 110.4 . . ? C5A C27A H27D 110.4 . . ? C5A C27A O2A 106.4(10) . . ? H27C C27A H27D 108.6 . . ? O2A C27A H27C 110.4 . . ? O2A C27A H27D 110.4 . . ? C27A O2A C28 122.5(9) . . ? C3A C20A H20C 109.6 . . ? C3A C20A H20D 109.6 . . ? H20C C20A H20D 108.1 . . ? O3A C20A C3A 110.3(11) . . ? O3A C20A H20C 109.6 . . ? O3A C20A H20D 109.6 . . ? C20A O3A C21A 113.4(11) . . ? O3B C21B C26B 122.0(14) . . ? O3B C21B C22B 120.4(13) . . ? C26B C21B C22B 116.6(17) . . ? C21B C26B H26B 118.7 . . ? C21B C26B C25B 122.6(15) . . ? C25B C26B H26B 118.7 . . ? C26B C25B H25B 120.5 . . ? C24B C25B C26B 118.9(12) . . ? C24B C25B H25B 120.5 . . ? C25B C24B C23B 121.7(11) . . ? C25B C24B I3B 123.5(8) . . ? C23B C24B I3B 114.8(8) . . ? C24B C23B H23B 120.9 . . ? C24B C23B C22B 118.1(14) . . ? C22B C23B H23B 120.9 . . ? C21B C22B C23B 120.7(18) . . ? C21B C22B H22B 119.6 . . ? C23B C22B H22B 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I1 C17 C16 C15 -176.5(4) . . . . ? O1 C14 C19 C18 -179.1(4) . . . . ? O1 C14 C15 C16 179.3(5) . . . . ? O1 C13 C1 C6 -85.6(6) . . . . ? O1 C13 C1 C2 88.6(6) . . . . ? C14 O1 C13 C1 175.6(4) . . . . ? C14 C19 C18 C17 -0.3(8) . . . . ? C14 C15 C16 C17 0.0(8) . . . . ? C6 C1 C2 C3B 11.2(10) . . . . ? C6 C1 C2 C7 -178.2(5) . . . . ? C6 C1 C2 C3A -14.5(11) . . . . ? C6 C5B C27B O2B 97.0(13) . . . . ? C6 C5B C4B C3B -4.4(18) . . . . ? C6 C5B C4B C9B 172.6(10) . . . . ? C6 C5A C27A O2A 71.8(14) . . . . ? C19 C14 C15 C16 -0.1(8) . . . . ? C19 C18 C17 I1 176.7(4) . . . . ? C19 C18 C17 C16 0.2(8) . . . . ? C23A C22A C21A C26A -13(4) . . . . ? C23A C22A C21A O3A 175(2) . . . . ? C22A C23A C24A I3A 176.0(16) . . . . ? C22A C23A C24A C25A -1(2) . . . . ? C22A C21A C26A C25A 11(3) . . . . ? C22A C21A O3A C20A 165.8(18) . . . . ? O3B C20B C3B C2 65.1(16) . . . . ? O3B C20B C3B C4B -111.5(14) . . . . ? O3B C21B C26B C25B 179.1(16) . . . . ? O3B C21B C22B C23B -177.4(19) . . . . ? C33 C28 O2B C27B -15.1(14) . . . . ? C33 C28 C29 C30 -2.0(10) . . . . ? C33 C28 O2A C27A -8.0(12) . . . . ? C33 C32 C31 I2 179.6(5) . . . . ? C33 C32 C31 C30 -1.2(10) . . . . ? C18 C17 C16 C15 0.0(8) . . . . ? C28 C33 C32 C31 -0.6(11) . . . . ? C28 O2B C27B C5B -172.5(11) . . . . ? C28 C29 C30 C31 0.2(10) . . . . ? C11 C6 C1 C13 -1.5(8) . . . . ? C11 C6 C1 C2 -175.7(5) . . . . ? C11 C6 C5B C27B -12.0(14) . . . . ? C11 C6 C5B C4B 172.4(9) . . . . ? C11 C6 C5A C4A -176.1(10) . . . . ? C11 C6 C5A C27A 14.4(16) . . . . ? C13 O1 C14 C19 0.2(7) . . . . ? C13 O1 C14 C15 -179.1(4) . . . . ? C13 C1 C2 C3B -163.0(8) . . . . ? C13 C1 C2 C7 7.7(8) . . . . ? C13 C1 C2 C3A 171.4(9) . . . . ? C15 C14 C19 C18 0.2(7) . . . . ? C1 C6 C11 C12 -93.1(7) . . . . ? C1 C6 C5B C27B -179.2(10) . . . . ? C1 C6 C5B C4B 5.2(15) . . . . ? C1 C6 C5A C4A -8.6(16) . . . . ? C1 C6 C5A C27A -178.1(10) . . . . ? C1 C2 C3B C20B 173.1(9) . . . . ? C1 C2 C3B C4B -10.2(16) . . . . ? C1 C2 C7 C8 83.7(7) . . . . ? C1 C2 C3A C4A 3.5(19) . . . . ? C1 C2 C3A C20A 171.6(11) . . . . ? O2B C28 C29 C30 176.5(7) . . . . ? O2B C28 O2A C27A -166(3) . . . . ? C2 C3B C4B C5B 6.7(18) . . . . ? C2 C3B C4B C9B -170.3(11) . . . . ? C2 C3A C20A O3A 84.7(16) . . . . ? C29 C28 O2B C27B 166.5(9) . . . . ? C29 C28 O2A C27A 165.5(9) . . . . ? C29 C30 C31 I2 -179.4(5) . . . . ? C29 C30 C31 C32 1.4(9) . . . . ? C5B C6 C11 C12 100.1(8) . . . . ? C5B C6 C1 C13 165.5(7) . . . . ? C5B C6 C1 C2 -8.7(10) . . . . ? C5B C6 C5A C4A 86(3) . . . . ? C5B C6 C5A C27A -84(4) . . . . ? C24A C23A C22A C21A 7(3) . . . . ? C24A C25A C26A C21A -4(2) . . . . ? C26A C21A O3A C20A -6(3) . . . . ? C26A C25A C24A I3A -177.7(10) . . . . ? C26A C25A C24A C23A -1(2) . . . . ? C27B C5B C4B C3B 179.7(12) . . . . ? C27B C5B C4B C9B -3.3(17) . . . . ? C32 C33 C28 O2B -175.9(9) . . . . ? C32 C33 C28 C29 2.2(10) . . . . ? C32 C33 C28 O2A 175.8(7) . . . . ? C20B O3B C21B C26B -26(3) . . . . ? C20B O3B C21B C22B 166.2(19) . . . . ? C20B C3B C4B C5B -176.7(12) . . . . ? C20B C3B C4B C9B 6.2(19) . . . . ? C3B C2 C7 C8 -105.9(10) . . . . ? C3B C2 C3A C4A -93(5) . . . . ? C3B C2 C3A C20A 75(4) . . . . ? C4A C5A C27A O2A -96.9(15) . . . . ? C4A C3A C20A O3A -106.6(16) . . . . ? C7 C2 C3B C20B 2.5(16) . . . . ? C7 C2 C3B C4B 179.2(10) . . . . ? C7 C2 C3A C4A 167.4(12) . . . . ? C7 C2 C3A C20A -24.6(17) . . . . ? C10B C9B C4B C5B -95.0(15) . . . . ? C10B C9B C4B C3B 81.9(16) . . . . ? C9A C4A C5A C6 176.9(13) . . . . ? C9A C4A C5A C27A -14(2) . . . . ? C9A C4A C3A C2 -174.3(13) . . . . ? C9A C4A C3A C20A 17(2) . . . . ? C4B C5B C27B O2B -86.9(14) . . . . ? C5A C6 C11 C12 74.0(10) . . . . ? C5A C6 C1 C13 -168.8(8) . . . . ? C5A C6 C1 C2 17.0(10) . . . . ? C5A C6 C5B C27B 83(3) . . . . ? C5A C6 C5B C4B -93(4) . . . . ? C5A C4A C9A C10A 83.7(18) . . . . ? C5A C4A C3A C2 5(2) . . . . ? C5A C4A C3A C20A -164.0(14) . . . . ? C5A C27A O2A C28 178.9(11) . . . . ? C3A C2 C3B C20B -91(5) . . . . ? C3A C2 C3B C4B 86(5) . . . . ? C3A C2 C7 C8 -79.7(10) . . . . ? C3A C4A C9A C10A -97.5(18) . . . . ? C3A C4A C5A C6 -2(2) . . . . ? C3A C4A C5A C27A 166.8(14) . . . . ? C3A C20A O3A C21A -170.6(17) . . . . ? O2A C28 O2B C27B 12(2) . . . . ? O2A C28 C29 C30 -175.2(7) . . . . ? O3A C21A C26A C25A -178.0(18) . . . . ? C21B O3B C20B C3B 179.8(18) . . . . ? C21B C26B C25B C24B 5(2) . . . . ? C26B C21B C22B C23B 14(3) . . . . ? C26B C25B C24B C23B 0.6(19) . . . . ? C26B C25B C24B I3B -178.3(10) . . . . ? C25B C24B C23B C22B 1(2) . . . . ? C24B C23B C22B C21B -8(3) . . . . ? C22B C21B C26B C25B -12(3) . . . . ? I3B C24B C23B C22B -180.0(15) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 962422' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-ea-118K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-ea, 118 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Cl3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Cl3 O5' _chemical_formula_weight 672.05 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.6153(3) _cell_length_b 13.3561(6) _cell_length_c 14.5104(8) _cell_angle_alpha 111.810(5) _cell_angle_beta 92.311(4) _cell_angle_gamma 90.228(3) _cell_volume 1728.31(13) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5766 _cell_measurement_temperature 118(2) _cell_measurement_theta_max 29.1095 _cell_measurement_theta_min 3.6105 _exptl_absorpt_coefficient_mu 0.306 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.77049 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 708 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_unetI/netI 0.0640 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 17252 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.17 _diffrn_reflns_theta_min 3.62 _diffrn_ambient_temperature 118(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.844 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0171091000 _diffrn_orient_matrix_UB_12 -0.0094490000 _diffrn_orient_matrix_UB_13 0.0432122000 _diffrn_orient_matrix_UB_21 -0.0007241000 _diffrn_orient_matrix_UB_22 0.0564256000 _diffrn_orient_matrix_UB_23 0.0272267000 _diffrn_orient_matrix_UB_31 -0.0718303000 _diffrn_orient_matrix_UB_32 0.0004791000 _diffrn_orient_matrix_UB_33 -0.0130072000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5903 _reflns_number_total 7900 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.707 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.120 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 401 _refine_ls_number_reflns 7900 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1399 _refine_ls_R_factor_gt 0.1196 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1247P)^2^+9.6580P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3345 _refine_ls_wR_factor_ref 0.3444 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 O2B-C15 \\sim O2A-C15 with sigma of 0.02 C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 3. Others Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)= Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C14A)=Sof(H14C)= Sof(H14D)=Sof(O3A)=Sof(C22A)=Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)= Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=Sof(Cl3A)=Sof(O2A)=1-FVAR(1) Sof(Cl3B)=Sof(O3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)= Sof(C25B)=Sof(C26B)=Sof(H26B)=Sof(C3B)=Sof(C5B)=Sof(C14B)=Sof(H14A)=Sof(H14B)= Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C4B)= Sof(C24B)=Sof(H24B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21A(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C14A(H14C,H14D), C21B(H21C,H21D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl2 Cl 0.98353(17) 0.11197(13) 0.96721(11) 0.0403(4) Uani 1 1 d . . . Cl1 Cl 1.71895(15) 0.03606(15) 0.12551(12) 0.0462(4) Uani 1 1 d . . . Cl3B Cl 0.5290(9) 0.9348(9) 0.3130(9) 0.077(3) Uani 0.605(14) 1 d A 1 . C9 C 1.3173(5) 0.1011(5) 0.1727(4) 0.0296(11) Uani 1 1 d . . . H9 H 1.2302 0.0748 0.1390 0.036 Uiso 1 1 calc . . R O3B O 0.6915(10) 0.5348(7) 0.3562(6) 0.030(2) Uiso 0.605(14) 1 d A 1 . C8 C 1.3236(5) 0.1868(4) 0.2644(4) 0.0274(10) Uani 1 1 d . . . C15 C 0.9342(6) 0.2457(4) 0.7242(4) 0.0342(13) Uani 1 1 d . . . C19 C 0.8394(6) 0.1482(5) 0.8184(5) 0.0348(12) Uani 1 1 d . . . H19 H 0.7643 0.1095 0.8312 0.042 Uiso 1 1 calc A . R C18 C 0.9644(6) 0.1655(4) 0.8749(4) 0.0297(11) Uani 1 1 d A . . C10 C 1.4399(6) 0.0551(5) 0.1317(4) 0.0322(11) Uani 1 1 d . . . H10 H 1.4372 -0.0044 0.0701 0.039 Uiso 1 1 calc . . R C12 C 1.5731(5) 0.1811(5) 0.2705(4) 0.0324(12) Uani 1 1 d . . . H12 H 1.6606 0.2086 0.3031 0.039 Uiso 1 1 calc . . R C13 C 1.4515(6) 0.2256(5) 0.3125(4) 0.0328(12) Uani 1 1 d . . . H13 H 1.4549 0.2836 0.3752 0.039 Uiso 1 1 calc . . R C20 C 0.8270(6) 0.1884(5) 0.7436(5) 0.0358(13) Uani 1 1 d A . . H20 H 0.7426 0.1762 0.7044 0.043 Uiso 1 1 calc . . R C22B C 0.6641(14) 0.6284(10) 0.3479(9) 0.035(3) Uiso 0.605(14) 1 d A 1 . C27B C 0.6984(12) 0.7273(8) 0.4218(10) 0.032(3) Uiso 0.605(14) 1 d A 1 . H27B H 0.7522 0.7309 0.4793 0.039 Uiso 0.605(14) 1 calc A 1 R C23B C 0.5930(12) 0.6213(11) 0.2620(10) 0.036(3) Uiso 0.605(14) 1 d A 1 . H23B H 0.5736 0.5529 0.2109 0.043 Uiso 0.605(14) 1 calc A 1 R C11 C 1.5659(5) 0.0954(5) 0.1800(4) 0.0316(11) Uani 1 1 d . . . C16 C 1.0594(7) 0.2638(5) 0.7821(5) 0.0405(14) Uani 1 1 d A . . H16 H 1.1342 0.3029 0.7694 0.049 Uiso 1 1 calc . . R C25B C 0.5794(10) 0.8126(9) 0.3245(9) 0.034(2) Uiso 0.605(14) 1 d A 1 . C26B C 0.6533(10) 0.8214(8) 0.4111(9) 0.032(2) Uiso 0.605(14) 1 d A 1 . H26B H 0.6727 0.8899 0.4619 0.038 Uiso 0.605(14) 1 calc A 1 R O1 O 1.2095(4) 0.2361(3) 0.3145(3) 0.0284(8) Uani 1 1 d A . . C2 C 0.9414(6) 0.2271(4) 0.4217(4) 0.0279(11) Uani 1 1 d . . . C1 C 0.9729(5) 0.2640(4) 0.3457(4) 0.0268(10) Uani 1 1 d A . . C28 C 0.9978(5) 0.1218(4) 0.4245(4) 0.0292(11) Uani 1 1 d A . . H28A H 1.0895 0.1086 0.3940 0.035 Uiso 1 1 calc . . R H28B H 1.0116 0.1286 0.4945 0.035 Uiso 1 1 calc . . R C21A C 0.837(2) 0.5485(13) 0.4382(11) 0.027(3) Uiso 0.395(14) 1 d A 2 . H21A H 0.8052 0.5926 0.5051 0.033 Uiso 0.395(14) 1 calc A 2 R H21B H 0.9214 0.5834 0.4263 0.033 Uiso 0.395(14) 1 calc A 2 R C7 C 1.0729(5) 0.2001(4) 0.2699(4) 0.0273(10) Uani 1 1 d . . . H7A H 1.0597 0.1219 0.2544 0.033 Uiso 1 1 calc A . R H7B H 1.0591 0.2141 0.2078 0.033 Uiso 1 1 calc . . R C32 C 0.9528(6) 0.4000(5) 0.2619(4) 0.0322(11) Uani 1 1 d A . . H32A H 1.0467 0.3767 0.2380 0.039 Uiso 1 1 calc . . R H32B H 0.9516 0.4798 0.2865 0.039 Uiso 1 1 calc . . R C6 C 0.9223(6) 0.3628(4) 0.3459(4) 0.0281(11) Uani 1 1 d . . . C33 C 0.8435(7) 0.3526(5) 0.1751(4) 0.0396(13) Uani 1 1 d . . . H33A H 0.8669 0.3750 0.1205 0.059 Uiso 1 1 calc A . GR H33B H 0.7512 0.3790 0.1979 0.059 Uiso 1 1 calc . . GR H33C H 0.8430 0.2737 0.1520 0.059 Uiso 1 1 calc . . GR C3B C 0.8361(14) 0.2814(12) 0.4884(11) 0.019(2) Uani 0.605(14) 1 d A 1 . C29 C 0.9012(6) 0.0263(4) 0.3700(5) 0.0368(13) Uani 1 1 d . . . H29A H 0.8939 0.0150 0.2993 0.055 Uiso 1 1 calc A . GR H29B H 0.8088 0.0404 0.3977 0.055 Uiso 1 1 calc . . GR H29C H 0.9384 -0.0385 0.3778 0.055 Uiso 1 1 calc . . GR C5B C 0.8248(15) 0.4194(11) 0.4179(11) 0.020(3) Uani 0.605(14) 1 d A 1 . C14B C 0.8019(12) 0.2437(8) 0.5709(8) 0.026(2) Uiso 0.605(14) 1 d A 1 . H14A H 0.7130 0.2744 0.5999 0.031 Uiso 0.605(14) 1 calc A 1 R H14B H 0.7934 0.1641 0.5454 0.031 Uiso 0.605(14) 1 calc A 1 R C4A C 0.8413(19) 0.4008(11) 0.5110(11) 0.023(3) Uani 0.395(14) 1 d A 2 . C30A C 0.7665(16) 0.4738(12) 0.6020(10) 0.034(4) Uani 0.395(14) 1 d A 2 . H30A H 0.7874 0.4515 0.6589 0.040 Uiso 0.395(14) 1 calc A 2 R H30B H 0.7993 0.5494 0.6206 0.040 Uiso 0.395(14) 1 calc A 2 R C30B C 0.6553(11) 0.4262(8) 0.5514(7) 0.026(2) Uani 0.605(14) 1 d A 1 . H30C H 0.5938 0.3678 0.5539 0.031 Uiso 0.605(14) 1 calc A 1 R H30D H 0.6002 0.4686 0.5201 0.031 Uiso 0.605(14) 1 calc A 1 R C31B C 0.6987(9) 0.5011(7) 0.6596(7) 0.029(2) Uani 0.605(14) 1 d A 1 . H31A H 0.7390 0.5686 0.6596 0.044 Uiso 0.605(14) 1 calc A 1 GR H31B H 0.7677 0.4650 0.6874 0.044 Uiso 0.605(14) 1 calc A 1 GR H31C H 0.6166 0.5169 0.7002 0.044 Uiso 0.605(14) 1 calc A 1 GR C17 C 1.0727(7) 0.2247(5) 0.8572(5) 0.0406(14) Uani 1 1 d . . . H17 H 1.1565 0.2380 0.8973 0.049 Uiso 1 1 calc A . R C4B C 0.7733(12) 0.3762(7) 0.4866(7) 0.0218(19) Uani 0.605(14) 1 d A 1 . C24B C 0.5498(13) 0.7142(9) 0.2503(10) 0.045(3) Uiso 0.605(14) 1 d A 1 . H24B H 0.4997 0.7103 0.1913 0.054 Uiso 0.605(14) 1 calc A 1 R C31A C 0.611(2) 0.465(2) 0.578(2) 0.057(6) Uani 0.395(14) 1 d A 2 . H31D H 0.5933 0.4665 0.5113 0.086 Uiso 0.395(14) 1 calc A 2 GR H31E H 0.5655 0.5265 0.6268 0.086 Uiso 0.395(14) 1 calc A 2 GR H31F H 0.5744 0.3978 0.5801 0.086 Uiso 0.395(14) 1 calc A 2 GR C3A C 0.883(2) 0.295(2) 0.504(2) 0.031(5) Uani 0.395(14) 1 d A 2 . C5A C 0.870(2) 0.436(2) 0.434(2) 0.025(5) Uani 0.395(14) 1 d A 2 . C14A C 0.841(2) 0.2591(13) 0.5890(13) 0.028(4) Uiso 0.395(14) 1 d A 2 . H14C H 0.7560 0.2961 0.6198 0.034 Uiso 0.395(14) 1 calc A 2 R H14D H 0.8239 0.1801 0.5643 0.034 Uiso 0.395(14) 1 calc A 2 R C21B C 0.7899(12) 0.5354(8) 0.4338(7) 0.024(2) Uiso 0.605(14) 1 d A 1 . H21C H 0.7494 0.5708 0.4995 0.029 Uiso 0.605(14) 1 calc A 1 R H21D H 0.8754 0.5760 0.4319 0.029 Uiso 0.605(14) 1 calc A 1 R O2B O 0.9173(10) 0.2819(6) 0.6456(5) 0.0284(19) Uiso 0.605(14) 1 d A 1 . O3A O 0.7292(16) 0.5430(11) 0.3644(10) 0.034(3) Uiso 0.395(14) 1 d A 2 . C22A C 0.6718(16) 0.6451(13) 0.3689(11) 0.022(4) Uiso 0.395(14) 1 d A 2 . C27A C 0.6970(15) 0.7416(10) 0.4489(13) 0.022(3) Uiso 0.395(14) 1 d A 2 . H27A H 0.7484 0.7418 0.5063 0.026 Uiso 0.395(14) 1 calc A 2 R C26A C 0.6471(12) 0.8380(10) 0.4453(10) 0.017(3) Uiso 0.395(14) 1 d A 2 . H26A H 0.6648 0.9039 0.5000 0.021 Uiso 0.395(14) 1 calc A 2 R C25A C 0.5718(11) 0.8375(9) 0.3617(9) 0.014(2) Uiso 0.395(14) 1 d A 2 . C24A C 0.5466(12) 0.7437(10) 0.2805(10) 0.017(3) Uiso 0.395(14) 1 d A 2 . H24A H 0.4995 0.7448 0.2221 0.021 Uiso 0.395(14) 1 calc A 2 R C23A C 0.5921(15) 0.6468(13) 0.2862(12) 0.024(4) Uiso 0.395(14) 1 d A 2 . H23A H 0.5686 0.5808 0.2331 0.029 Uiso 0.395(14) 1 calc A 2 R Cl3A Cl 0.5076(13) 0.9545(10) 0.3532(10) 0.053(2) Uani 0.395(14) 1 d A 2 . O2A O 0.9584(16) 0.2903(9) 0.6585(9) 0.032(3) Uiso 0.395(14) 1 d 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 Cl2 0.0481(8) 0.0435(8) 0.0350(7) 0.0205(6) 0.0067(6) 0.0060(6) Cl1 0.0258(7) 0.0616(10) 0.0480(9) 0.0162(8) 0.0059(6) 0.0097(6) Cl3B 0.034(3) 0.073(5) 0.165(9) 0.093(6) -0.018(4) -0.003(2) C9 0.021(2) 0.034(3) 0.032(3) 0.010(2) 0.0018(19) -0.003(2) C8 0.024(2) 0.025(2) 0.031(3) 0.008(2) 0.003(2) -0.0005(19) C15 0.048(3) 0.020(2) 0.040(3) 0.015(2) 0.021(3) 0.008(2) C19 0.032(3) 0.037(3) 0.046(3) 0.026(3) 0.011(2) 0.007(2) C18 0.038(3) 0.022(2) 0.031(3) 0.012(2) 0.012(2) 0.008(2) C10 0.031(3) 0.034(3) 0.030(3) 0.009(2) 0.004(2) 0.001(2) C12 0.021(2) 0.036(3) 0.040(3) 0.015(2) -0.007(2) -0.010(2) C13 0.032(3) 0.029(3) 0.033(3) 0.006(2) -0.002(2) 0.001(2) C20 0.035(3) 0.035(3) 0.049(3) 0.027(3) 0.013(2) 0.007(2) C11 0.024(2) 0.034(3) 0.039(3) 0.016(2) 0.005(2) 0.004(2) C16 0.055(4) 0.025(3) 0.041(3) 0.010(2) 0.019(3) -0.009(2) O1 0.0218(17) 0.0251(18) 0.0326(18) 0.0043(15) -0.0001(14) -0.0007(14) C2 0.033(3) 0.018(2) 0.034(3) 0.011(2) 0.005(2) 0.0020(19) C1 0.026(2) 0.027(3) 0.027(2) 0.009(2) 0.0003(19) -0.001(2) C28 0.028(2) 0.022(2) 0.039(3) 0.013(2) 0.005(2) 0.009(2) C7 0.024(2) 0.024(2) 0.032(3) 0.008(2) -0.001(2) -0.0024(19) C32 0.030(3) 0.036(3) 0.036(3) 0.020(2) 0.001(2) -0.002(2) C6 0.037(3) 0.022(2) 0.029(2) 0.013(2) 0.005(2) 0.001(2) C33 0.045(3) 0.043(3) 0.031(3) 0.015(3) -0.004(2) 0.002(3) C3B 0.022(7) 0.015(5) 0.024(6) 0.013(5) 0.005(5) 0.006(5) C29 0.040(3) 0.020(3) 0.050(3) 0.012(2) 0.007(3) 0.005(2) C5B 0.029(8) 0.012(5) 0.020(6) 0.007(4) -0.006(5) 0.001(5) C4A 0.022(7) 0.018(6) 0.033(7) 0.013(5) 0.003(6) -0.001(6) C30A 0.049(9) 0.027(7) 0.027(7) 0.012(6) 0.000(6) -0.007(6) C30B 0.018(5) 0.021(5) 0.037(5) 0.009(4) 0.003(4) 0.005(3) C31B 0.031(5) 0.024(4) 0.029(5) 0.005(3) 0.006(4) -0.002(3) C17 0.044(3) 0.035(3) 0.038(3) 0.007(3) 0.006(3) -0.009(3) C4B 0.019(5) 0.016(4) 0.029(4) 0.007(3) 0.002(4) 0.001(3) C31A 0.028(10) 0.071(16) 0.103(19) 0.066(15) 0.024(10) 0.014(9) C3A 0.025(12) 0.032(10) 0.037(11) 0.013(8) -0.007(9) -0.005(9) C5A 0.024(11) 0.024(10) 0.026(10) 0.008(8) -0.012(8) -0.004(8) Cl3A 0.033(4) 0.041(3) 0.103(7) 0.050(4) -0.008(3) -0.001(2) _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 Cl2 C18 1.742(5) . ? Cl1 C11 1.749(5) . ? Cl3B C25B 1.768(13) . ? C9 H9 0.9500 . ? C9 C8 1.394(7) . ? C9 C10 1.382(7) . ? O3B C22B 1.326(15) . ? O3B C21B 1.439(13) . ? C8 C13 1.387(7) . ? C8 O1 1.372(6) . ? C15 C20 1.380(8) . ? C15 C16 1.406(10) . ? C15 O2B 1.400(8) . ? C15 O2A 1.326(11) . ? C19 H19 0.9500 . ? C19 C18 1.395(8) . ? C19 C20 1.379(8) . ? C18 C17 1.393(8) . ? C10 H10 0.9500 . ? C10 C11 1.376(8) . ? C12 H12 0.9500 . ? C12 C13 1.373(8) . ? C12 C11 1.384(8) . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C22B C27B 1.385(12) . ? C22B C23B 1.369(12) . ? C27B H27B 0.9500 . ? C27B C26B 1.391(10) . ? C23B H23B 0.9500 . ? C23B C24B 1.377(11) . ? C16 H16 0.9500 . ? C16 C17 1.375(9) . ? C25B C26B 1.383(11) . ? C25B C24B 1.374(11) . ? C26B H26B 0.9500 . ? O1 C7 1.438(6) . ? C2 C1 1.407(7) . ? C2 C28 1.523(7) . ? C2 C3B 1.432(15) . ? C2 C3A 1.35(3) . ? C1 C7 1.502(7) . ? C1 C6 1.407(7) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.516(8) . ? C21A H21A 0.9900 . ? C21A H21B 0.9900 . ? C21A C5A 1.51(3) . ? C21A O3A 1.44(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C6 1.516(7) . ? C32 C33 1.545(8) . ? C6 C5B 1.428(17) . ? C6 C5A 1.40(3) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C3B C14B 1.507(17) . ? C3B C4B 1.413(16) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C5B C4B 1.427(17) . ? C5B C21B 1.520(17) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C14B O2B 1.468(13) . ? C4A C30A 1.528(19) . ? C4A C3A 1.45(3) . ? C4A C5A 1.40(3) . ? C30A H30A 0.9900 . ? C30A H30B 0.9900 . ? C30A C31A 1.51(2) . ? C30B H30C 0.9900 . ? C30B H30D 0.9900 . ? C30B C31B 1.554(13) . ? C30B C4B 1.498(14) . ? C31B H31A 0.9800 . ? C31B H31B 0.9800 . ? C31B H31C 0.9800 . ? C17 H17 0.9500 . ? C24B H24B 0.9500 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C3A C14A 1.54(3) . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? C14A O2A 1.43(2) . ? C21B H21C 0.9900 . ? C21B H21D 0.9900 . ? O3A C22A 1.45(2) . ? C22A C27A 1.389(13) . ? C22A C23A 1.404(13) . ? C27A H27A 0.9500 . ? C27A C26A 1.394(12) . ? C26A H26A 0.9500 . ? C26A C25A 1.386(12) . ? C25A C24A 1.376(12) . ? C25A Cl3A 1.727(16) . ? C24A H24A 0.9500 . ? C24A C23A 1.398(12) . ? C23A H23A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C10 C9 C8 119.0(5) . . ? C22B O3B C21B 117.6(9) . . ? C13 C8 C9 120.1(5) . . ? O1 C8 C9 124.5(5) . . ? O1 C8 C13 115.4(5) . . ? C20 C15 C16 119.3(5) . . ? C20 C15 O2B 119.2(7) . . ? O2B C15 C16 121.5(6) . . ? O2A C15 C20 136.9(9) . . ? O2A C15 C16 103.7(8) . . ? O2A C15 O2B 17.7(6) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C20 C19 C18 118.7(5) . . ? C19 C18 Cl2 119.3(4) . . ? C17 C18 Cl2 120.5(5) . . ? C17 C18 C19 120.2(5) . . ? C9 C10 H10 119.9 . . ? C11 C10 C9 120.1(5) . . ? C11 C10 H10 119.9 . . ? C13 C12 H12 120.6 . . ? C13 C12 C11 118.8(5) . . ? C11 C12 H12 120.6 . . ? C8 C13 H13 119.6 . . ? C12 C13 C8 120.8(5) . . ? C12 C13 H13 119.6 . . ? C15 C20 H20 119.2 . . ? C19 C20 C15 121.7(6) . . ? C19 C20 H20 119.2 . . ? O3B C22B C27B 123.4(10) . . ? O3B C22B C23B 115.2(10) . . ? C23B C22B C27B 121.4(11) . . ? C22B C27B H27B 120.3 . . ? C22B C27B C26B 119.5(10) . . ? C26B C27B H27B 120.3 . . ? C22B C23B H23B 120.3 . . ? C22B C23B C24B 119.3(12) . . ? C24B C23B H23B 120.3 . . ? C10 C11 Cl1 118.9(4) . . ? C10 C11 C12 121.3(5) . . ? C12 C11 Cl1 119.8(4) . . ? C15 C16 H16 120.2 . . ? C17 C16 C15 119.6(5) . . ? C17 C16 H16 120.2 . . ? C26B C25B Cl3B 116.5(8) . . ? C24B C25B Cl3B 121.8(8) . . ? C24B C25B C26B 121.7(10) . . ? C27B C26B H26B 120.9 . . ? C25B C26B C27B 118.3(10) . . ? C25B C26B H26B 120.9 . . ? C8 O1 C7 118.9(4) . . ? C1 C2 C28 121.9(5) . . ? C1 C2 C3B 118.2(7) . . ? C3B C2 C28 119.1(7) . . ? C3A C2 C1 119.6(13) . . ? C3A C2 C28 117.3(13) . . ? C3A C2 C3B 20.4(8) . . ? C2 C1 C7 118.0(5) . . ? C2 C1 C6 120.9(5) . . ? C6 C1 C7 120.9(5) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? H28A C28 H28B 107.8 . . ? C29 C28 C2 112.5(5) . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? H21A C21A H21B 108.1 . . ? C5A C21A H21A 109.6 . . ? C5A C21A H21B 109.6 . . ? O3A C21A H21A 109.6 . . ? O3A C21A H21B 109.6 . . ? O3A C21A C5A 110.1(14) . . ? O1 C7 C1 105.5(4) . . ? O1 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? H7A C7 H7B 108.8 . . ? H32A C32 H32B 108.1 . . ? C6 C32 H32A 109.5 . . ? C6 C32 H32B 109.5 . . ? C6 C32 C33 110.6(5) . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? C1 C6 C32 120.5(5) . . ? C1 C6 C5B 118.9(7) . . ? C5B C6 C32 119.9(7) . . ? C5A C6 C1 118.6(12) . . ? C5A C6 C32 119.4(12) . . ? C5A C6 C5B 20.2(7) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 119.0(10) . . ? C4B C3B C2 122.4(11) . . ? C4B C3B C14B 118.3(11) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C21B 120.2(11) . . ? C4B C5B C6 121.7(11) . . ? C4B C5B C21B 117.5(12) . . ? C3B C14B H14A 110.5 . . ? C3B C14B H14B 110.5 . . ? H14A C14B H14B 108.7 . . ? O2B C14B C3B 106.1(9) . . ? O2B C14B H14A 110.5 . . ? O2B C14B H14B 110.5 . . ? C3A C4A C30A 119.9(16) . . ? C5A C4A C30A 120.5(15) . . ? C5A C4A C3A 119.7(19) . . ? C4A C30A H30A 109.8 . . ? C4A C30A H30B 109.8 . . ? H30A C30A H30B 108.3 . . ? C31A C30A C4A 109.2(17) . . ? C31A C30A H30A 109.8 . . ? C31A C30A H30B 109.8 . . ? H30C C30B H30D 107.5 . . ? C31B C30B H30C 108.5 . . ? C31B C30B H30D 108.5 . . ? C4B C30B H30C 108.5 . . ? C4B C30B H30D 108.5 . . ? C4B C30B C31B 115.2(9) . . ? C18 C17 H17 119.8 . . ? C16 C17 C18 120.5(6) . . ? C16 C17 H17 119.8 . . ? C3B C4B C5B 116.8(10) . . ? C3B C4B C30B 121.3(9) . . ? C5B C4B C30B 122.0(9) . . ? C23B C24B H24B 120.1 . . ? C25B C24B C23B 119.8(11) . . ? C25B C24B H24B 120.1 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 120(2) . . ? C2 C3A C14A 123(2) . . ? C4A C3A C14A 117(2) . . ? C6 C5A C21A 118(2) . . ? C6 C5A C4A 119(2) . . ? C4A C5A C21A 123(2) . . ? C3A C14A H14C 111.0 . . ? C3A C14A H14D 111.0 . . ? H14C C14A H14D 109.0 . . ? O2A C14A C3A 104.0(13) . . ? O2A C14A H14C 111.0 . . ? O2A C14A H14D 111.0 . . ? O3B C21B C5B 108.5(9) . . ? O3B C21B H21C 110.0 . . ? O3B C21B H21D 110.0 . . ? C5B C21B H21C 110.0 . . ? C5B C21B H21D 110.0 . . ? H21C C21B H21D 108.4 . . ? C15 O2B C14B 122.2(7) . . ? C21A O3A C22A 116.4(12) . . ? C27A C22A O3A 123.2(12) . . ? C27A C22A C23A 118.6(14) . . ? C23A C22A O3A 118.2(13) . . ? C22A C27A H27A 119.9 . . ? C22A C27A C26A 120.3(13) . . ? C26A C27A H27A 119.9 . . ? C27A C26A H26A 120.1 . . ? C25A C26A C27A 119.8(12) . . ? C25A C26A H26A 120.1 . . ? C26A C25A Cl3A 121.8(9) . . ? C24A C25A C26A 121.5(10) . . ? C24A C25A Cl3A 116.7(9) . . ? C25A C24A H24A 120.8 . . ? C25A C24A C23A 118.3(11) . . ? C23A C24A H24A 120.8 . . ? C22A C23A H23A 119.3 . . ? C24A C23A C22A 121.4(14) . . ? C24A C23A H23A 119.3 . . ? C15 O2A C14A 105.1(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C18 C17 C16 177.8(5) . . . . ? Cl3B C25B C26B C27B -178.2(9) . . . . ? Cl3B C25B C24B C23B 179.0(10) . . . . ? C9 C8 C13 C12 0.5(9) . . . . ? C9 C8 O1 C7 -1.6(8) . . . . ? C9 C10 C11 Cl1 -179.4(4) . . . . ? C9 C10 C11 C12 0.9(9) . . . . ? O3B C22B C27B C26B -173.5(11) . . . . ? O3B C22B C23B C24B 174.6(11) . . . . ? C8 C9 C10 C11 -1.5(8) . . . . ? C8 O1 C7 C1 176.1(4) . . . . ? C15 C16 C17 C18 1.2(9) . . . . ? C19 C18 C17 C16 -1.9(9) . . . . ? C18 C19 C20 C15 -0.6(9) . . . . ? C10 C9 C8 C13 0.8(8) . . . . ? C10 C9 C8 O1 -177.2(5) . . . . ? C13 C8 O1 C7 -179.7(5) . . . . ? C13 C12 C11 Cl1 -179.2(4) . . . . ? C13 C12 C11 C10 0.5(9) . . . . ? C20 C15 C16 C17 -0.3(8) . . . . ? C20 C15 O2B C14B -12.3(10) . . . . ? C20 C15 O2A C14A -5.7(15) . . . . ? C20 C19 C18 Cl2 -178.1(4) . . . . ? C20 C19 C18 C17 1.6(8) . . . . ? C22B O3B C21B C5B -169.8(11) . . . . ? C22B C27B C26B C25B -2.3(17) . . . . ? C22B C23B C24B C25B 0.5(18) . . . . ? C27B C22B C23B C24B -2.6(19) . . . . ? C23B C22B C27B C26B 3.5(19) . . . . ? C11 C12 C13 C8 -1.1(9) . . . . ? C16 C15 C20 C19 0.0(9) . . . . ? C16 C15 O2B C14B 165.9(7) . . . . ? C16 C15 O2A C14A 171.5(9) . . . . ? C26B C25B C24B C23B 0.6(18) . . . . ? O1 C8 C13 C12 178.7(5) . . . . ? C2 C1 C7 O1 -83.1(6) . . . . ? C2 C1 C6 C32 -177.9(5) . . . . ? C2 C1 C6 C5B -7.3(10) . . . . ? C2 C1 C6 C5A 15.8(12) . . . . ? C2 C3B C14B O2B 74.8(12) . . . . ? C2 C3B C4B C5B -3.1(17) . . . . ? C2 C3B C4B C30B 174.9(11) . . . . ? C2 C3A C14A O2A 95.1(18) . . . . ? C1 C2 C28 C29 -90.5(6) . . . . ? C1 C2 C3B C14B -179.4(8) . . . . ? C1 C2 C3B C4B -6.3(15) . . . . ? C1 C2 C3A C4A 6(2) . . . . ? C1 C2 C3A C14A 177.8(13) . . . . ? C1 C6 C5B C4B -2.7(14) . . . . ? C1 C6 C5B C21B 167.9(8) . . . . ? C1 C6 C5A C21A 170.8(11) . . . . ? C1 C6 C5A C4A -14.1(19) . . . . ? C28 C2 C1 C7 -4.2(8) . . . . ? C28 C2 C1 C6 -178.5(5) . . . . ? C28 C2 C3B C14B 10.5(14) . . . . ? C28 C2 C3B C4B -176.5(9) . . . . ? C28 C2 C3A C4A 173.2(13) . . . . ? C28 C2 C3A C14A -15(2) . . . . ? C21A O3A C22A C27A -12(2) . . . . ? C21A O3A C22A C23A 165.2(14) . . . . ? C7 C1 C6 C32 7.9(8) . . . . ? C7 C1 C6 C5B 178.5(7) . . . . ? C7 C1 C6 C5A -158.4(10) . . . . ? C32 C6 C5B C4B 168.0(9) . . . . ? C32 C6 C5B C21B -21.4(14) . . . . ? C32 C6 C5A C21A 4.4(19) . . . . ? C32 C6 C5A C4A 179.5(12) . . . . ? C6 C1 C7 O1 91.3(6) . . . . ? C6 C5B C4B C3B 7.7(17) . . . . ? C6 C5B C4B C30B -170.3(11) . . . . ? C6 C5B C21B O3B 79.6(12) . . . . ? C33 C32 C6 C1 86.1(6) . . . . ? C33 C32 C6 C5B -84.4(9) . . . . ? C33 C32 C6 C5A -107.7(11) . . . . ? C3B C2 C1 C7 -174.0(8) . . . . ? C3B C2 C1 C6 11.6(10) . . . . ? C3B C2 C28 C29 79.2(9) . . . . ? C3B C2 C3A C4A -86(5) . . . . ? C3B C2 C3A C14A 86(5) . . . . ? C3B C14B O2B C15 -168.2(8) . . . . ? C5B C6 C5A C21A -93(5) . . . . ? C5B C6 C5A C4A 82(5) . . . . ? C14B C3B C4B C5B 170.0(11) . . . . ? C14B C3B C4B C30B -12.0(17) . . . . ? C4A C3A C14A O2A -92.6(17) . . . . ? C30A C4A C3A C2 175.9(16) . . . . ? C30A C4A C3A C14A 3(2) . . . . ? C30A C4A C5A C21A 3(3) . . . . ? C30A C4A C5A C6 -171.7(15) . . . . ? C31B C30B C4B C3B 83.1(13) . . . . ? C31B C30B C4B C5B -99.0(12) . . . . ? C4B C3B C14B O2B -98.6(11) . . . . ? C4B C5B C21B O3B -109.4(11) . . . . ? C24B C25B C26B C27B 0.3(16) . . . . ? C3A C2 C1 C7 162.7(11) . . . . ? C3A C2 C1 C6 -11.7(13) . . . . ? C3A C2 C28 C29 102.4(11) . . . . ? C3A C2 C3B C14B -80(5) . . . . ? C3A C2 C3B C4B 93(5) . . . . ? C3A C4A C30A C31A -97.9(18) . . . . ? C3A C4A C5A C21A -176.6(17) . . . . ? C3A C4A C5A C6 9(2) . . . . ? C3A C14A O2A C15 -170.5(15) . . . . ? C5A C21A O3A C22A 171.5(16) . . . . ? C5A C6 C5B C4B -98(5) . . . . ? C5A C6 C5B C21B 73(4) . . . . ? C5A C4A C30A C31A 82.4(19) . . . . ? C5A C4A C3A C2 -4(3) . . . . ? C5A C4A C3A C14A -176.9(16) . . . . ? C21B O3B C22B C27B -15.6(17) . . . . ? C21B O3B C22B C23B 167.3(10) . . . . ? C21B C5B C4B C3B -163.2(11) . . . . ? C21B C5B C4B C30B 18.8(16) . . . . ? O2B C15 C20 C19 178.2(6) . . . . ? O2B C15 C16 C17 -178.5(6) . . . . ? O2B C15 O2A C14A -9.5(18) . . . . ? O3A C21A C5A C6 62(2) . . . . ? O3A C21A C5A C4A -113.0(17) . . . . ? O3A C22A C27A C26A 175.3(14) . . . . ? O3A C22A C23A C24A -172.8(14) . . . . ? C22A C27A C26A C25A 0(2) . . . . ? C27A C22A C23A C24A 4(2) . . . . ? C27A C26A C25A C24A -1.2(18) . . . . ? C27A C26A C25A Cl3A 180.0(11) . . . . ? C26A C25A C24A C23A 3.7(18) . . . . ? C25A C24A C23A C22A -5(2) . . . . ? C23A C22A C27A C26A -2(2) . . . . ? Cl3A C25A C24A C23A -177.4(11) . . . . ? O2A C15 C20 C19 176.9(9) . . . . ? O2A C15 C16 C17 -178.1(7) . . . . ? O2A C15 O2B C14B 165(3) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.007 0.000 0.500 345 38 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962423' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cl-ea-154K _audit_creation_date 2013-12-24 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_name_common 'Cl-ea, 154 K' _chemical_name_systematic ; 2,4,6-triethyl-1,3,5-tris(4-chlorophenoxy)methylbenzene, ethyl acetate ; _chemical_formula_moiety 'C33 H33 Cl3 O3, C4 H8 O2' _chemical_formula_sum 'C37 H41 Cl3 O5' _chemical_formula_weight 672.05 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.6338(4) _cell_length_b 13.3820(8) _cell_length_c 14.5496(11) _cell_angle_alpha 111.658(6) _cell_angle_beta 92.203(5) _cell_angle_gamma 90.170(4) _cell_volume 1741.71(18) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4108 _cell_measurement_temperature 154(2) _cell_measurement_theta_max 29.1360 _cell_measurement_theta_min 4.0747 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 708 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_unetI/netI 0.0705 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 15021 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.20 _diffrn_reflns_theta_min 4.08 _diffrn_ambient_temperature 154(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.833 _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0169853000 _diffrn_orient_matrix_UB_12 -0.0098834000 _diffrn_orient_matrix_UB_13 0.0429296000 _diffrn_orient_matrix_UB_21 -0.0011149000 _diffrn_orient_matrix_UB_22 0.0561756000 _diffrn_orient_matrix_UB_23 0.0273359000 _diffrn_orient_matrix_UB_31 -0.0717007000 _diffrn_orient_matrix_UB_32 0.0003851000 _diffrn_orient_matrix_UB_33 -0.0128898000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5478 _reflns_number_total 7875 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.542 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.103 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 401 _refine_ls_number_reflns 7875 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1350 _refine_ls_R_factor_gt 0.1068 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1358P)^2^+6.7705P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3099 _refine_ls_wR_factor_ref 0.3252 _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. 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C27B-C22B \\sim C27B-C26B \\sim C26B-C25B \\sim C25B-C24B \\sim C24B-C23B \\sim C23B-C22B with sigma of 0.02 C27A-C22A \\sim C27A-C26A \\sim C26A-C25A \\sim C25A-C24A \\sim C24A-C23A \\sim C23A-C22A with sigma of 0.02 O2B-C15 \\sim O2A-C15 with sigma of 0.02 3. Others Sof(O2A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C4A)=Sof(C30A)=Sof(H30A)=Sof(H30B)= Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C3A)=Sof(C5A)=Sof(C14A)=Sof(H14C)= Sof(H14D)=Sof(O3A)=Sof(C22A)=Sof(C27A)=Sof(H27A)=Sof(C26A)=Sof(H26A)=Sof(C25A)= Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=Sof(Cl3A)=1-FVAR(1) Sof(Cl3B)=Sof(O3B)=Sof(C22B)=Sof(C27B)=Sof(H27B)=Sof(C23B)=Sof(H23B)= Sof(C25B)=Sof(C26B)=Sof(H26B)=Sof(C3B)=Sof(C5B)=Sof(C14B)=Sof(H14A)=Sof(H14B)= Sof(C30B)=Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C4B)= Sof(C24B)=Sof(H24B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(O2B)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C28(H28A,H28B), C21A(H21A,H21B), C7(H7A,H7B), C32(H32A,H32B), C14B(H14A,H14B), C30A(H30A,H30B), C30B(H30C,H30D), C14A(H14C,H14D), C21B(H21C,H21D) 4.b Aromatic/amide H refined with riding coordinates: C9(H9), C19(H19), C10(H10), C12(H12), C13(H13), C20(H20), C27B(H27B), C23B(H23B), C16(H16), C26B(H26B), C17(H17), C24B(H24B), C27A(H27A), C26A(H26A), C24A(H24A), C23A(H23A) 4.c Idealised Me refined as rotating group: C33(H33A,H33B,H33C), C29(H29A,H29B,H29C), C31B(H31A,H31B,H31C), C31A(H31D, H31E,H31F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn Cl2 Cl 0.98186(16) 0.11192(13) 0.96608(10) 0.0479(4) Uani 1 1 d . . . Cl1 Cl 1.71866(14) 0.03637(14) 0.12589(11) 0.0516(4) Uani 1 1 d . . . Cl3B Cl 0.5267(16) 0.9365(12) 0.3185(11) 0.084(4) Uani 0.633(13) 1 d A 1 . O2A O 0.9568(16) 0.2903(10) 0.6583(9) 0.037(3) Uiso 0.367(13) 1 d A 2 . C9 C 1.3180(5) 0.1020(4) 0.1732(4) 0.0309(10) Uani 1 1 d . . . H9 H 1.2310 0.0764 0.1395 0.037 Uiso 1 1 calc . . R O3B O 0.6944(9) 0.5348(6) 0.3568(5) 0.0327(19) Uiso 0.633(13) 1 d A 1 . C8 C 1.3241(5) 0.1874(4) 0.2652(4) 0.0295(10) Uani 1 1 d . . . C15 C 0.9332(6) 0.2452(4) 0.7233(4) 0.0356(11) Uani 1 1 d . . . C19 C 0.8387(5) 0.1476(5) 0.8176(4) 0.0384(12) Uani 1 1 d . . . H19 H 0.7641 0.1085 0.8303 0.046 Uiso 1 1 calc A . R C18 C 0.9623(5) 0.1655(4) 0.8739(4) 0.0345(11) Uani 1 1 d A . . C10 C 1.4402(5) 0.0553(4) 0.1322(4) 0.0330(10) Uani 1 1 d . . . H10 H 1.4373 -0.0042 0.0710 0.040 Uiso 1 1 calc . . R C12 C 1.5732(5) 0.1805(4) 0.2705(4) 0.0366(11) Uani 1 1 d . . . H12 H 1.6604 0.2073 0.3032 0.044 Uiso 1 1 calc . . R C13 C 1.4511(5) 0.2253(4) 0.3119(4) 0.0366(11) Uani 1 1 d . . . H13 H 1.4547 0.2835 0.3740 0.044 Uiso 1 1 calc . . R C20 C 0.8260(6) 0.1877(4) 0.7424(4) 0.0386(12) Uani 1 1 d A . . H20 H 0.7420 0.1753 0.7032 0.046 Uiso 1 1 calc . . R C22B C 0.6649(12) 0.6294(9) 0.3502(8) 0.035(3) Uiso 0.633(13) 1 d A 1 . C27B C 0.6970(12) 0.7274(8) 0.4241(9) 0.037(3) Uiso 0.633(13) 1 d A 1 . H27B H 0.7485 0.7301 0.4820 0.044 Uiso 0.633(13) 1 calc A 1 R C23B C 0.5930(11) 0.6220(10) 0.2639(9) 0.040(3) Uiso 0.633(13) 1 d A 1 . H23B H 0.5739 0.5542 0.2126 0.048 Uiso 0.633(13) 1 calc A 1 R C11 C 1.5656(5) 0.0953(4) 0.1800(4) 0.0343(11) Uani 1 1 d . . . C16 C 1.0572(6) 0.2634(4) 0.7807(4) 0.0424(13) Uani 1 1 d A . . H16 H 1.1316 0.3025 0.7679 0.051 Uiso 1 1 calc . . R C25B C 0.5793(9) 0.8140(8) 0.3275(8) 0.036(2) Uiso 0.633(13) 1 d A 1 . C26B C 0.6541(9) 0.8227(8) 0.4140(8) 0.035(2) Uiso 0.633(13) 1 d A 1 . H26B H 0.6751 0.8908 0.4643 0.042 Uiso 0.633(13) 1 calc A 1 R O1 O 1.2097(3) 0.2363(3) 0.3144(3) 0.0323(7) Uani 1 1 d A . . C2 C 0.9415(5) 0.2270(4) 0.4216(4) 0.0293(10) Uani 1 1 d . . . C1 C 0.9734(5) 0.2638(4) 0.3457(3) 0.0293(9) Uani 1 1 d A . . C28 C 0.9984(5) 0.1221(4) 0.4242(4) 0.0306(10) Uani 1 1 d A . . H28A H 1.0897 0.1090 0.3932 0.037 Uiso 1 1 calc . . R H28B H 1.0130 0.1288 0.4940 0.037 Uiso 1 1 calc . . R C21A C 0.8373(19) 0.5484(13) 0.4379(11) 0.029(3) Uiso 0.367(13) 1 d A 2 . H21A H 0.8073 0.5925 0.5049 0.035 Uiso 0.367(13) 1 calc A 2 R H21B H 0.9221 0.5823 0.4251 0.035 Uiso 0.367(13) 1 calc A 2 R C7 C 1.0741(5) 0.2004(4) 0.2705(4) 0.0303(10) Uani 1 1 d . . . H7A H 1.0613 0.1224 0.2554 0.036 Uiso 1 1 calc A . R H7B H 1.0602 0.2140 0.2084 0.036 Uiso 1 1 calc . . R C32 C 0.9540(5) 0.4008(4) 0.2630(4) 0.0365(11) Uani 1 1 d A . . H32A H 1.0481 0.3779 0.2395 0.044 Uiso 1 1 calc . . R H32B H 0.9524 0.4803 0.2877 0.044 Uiso 1 1 calc . . R C6 C 0.9233(5) 0.3630(4) 0.3465(4) 0.0324(10) Uani 1 1 d . . . C33 C 0.8454(6) 0.3535(5) 0.1759(4) 0.0467(14) Uani 1 1 d . . . H33A H 0.8692 0.3765 0.1217 0.070 Uiso 1 1 calc A . GR H33B H 0.7530 0.3794 0.1983 0.070 Uiso 1 1 calc . . GR H33C H 0.8455 0.2748 0.1525 0.070 Uiso 1 1 calc . . GR C3B C 0.8365(11) 0.2818(12) 0.4892(10) 0.023(2) Uani 0.633(13) 1 d A 1 . C29 C 0.9017(6) 0.0266(4) 0.3705(4) 0.0412(12) Uani 1 1 d . . . H29A H 0.8959 0.0141 0.2997 0.062 Uiso 1 1 calc A . GR H29B H 0.8090 0.0416 0.3973 0.062 Uiso 1 1 calc . . GR H29C H 0.9379 -0.0375 0.3799 0.062 Uiso 1 1 calc . . GR C5B C 0.8266(16) 0.4188(14) 0.4176(13) 0.027(3) Uani 0.633(13) 1 d A 1 . C14B C 0.8018(11) 0.2437(8) 0.5705(7) 0.030(2) Uiso 0.633(13) 1 d A 1 . H14A H 0.7132 0.2747 0.5998 0.036 Uiso 0.633(13) 1 calc A 1 R H14B H 0.7929 0.1643 0.5450 0.036 Uiso 0.633(13) 1 calc A 1 R C4A C 0.8406(18) 0.4004(12) 0.5103(11) 0.025(3) Uani 0.367(13) 1 d A 2 . C30A C 0.7672(14) 0.4732(11) 0.6004(10) 0.031(4) Uani 0.367(13) 1 d A 2 . H30A H 0.8015 0.5482 0.6197 0.038 Uiso 0.367(13) 1 calc A 2 R H30B H 0.7853 0.4498 0.6569 0.038 Uiso 0.367(13) 1 calc A 2 R C30B C 0.6573(10) 0.4268(7) 0.5514(7) 0.032(2) Uani 0.633(13) 1 d A 1 . H30C H 0.5950 0.3689 0.5537 0.038 Uiso 0.633(13) 1 calc A 1 R H30D H 0.6033 0.4694 0.5201 0.038 Uiso 0.633(13) 1 calc A 1 R C31B C 0.6989(9) 0.5011(7) 0.6596(6) 0.038(2) Uani 0.633(13) 1 d A 1 . H31A H 0.7363 0.5695 0.6601 0.057 Uiso 0.633(13) 1 calc A 1 GR H31B H 0.7696 0.4660 0.6868 0.057 Uiso 0.633(13) 1 calc A 1 GR H31C H 0.6168 0.5146 0.6999 0.057 Uiso 0.633(13) 1 calc A 1 GR C17 C 1.0711(6) 0.2240(5) 0.8567(4) 0.0445(13) Uani 1 1 d . . . H17 H 1.1546 0.2370 0.8967 0.053 Uiso 1 1 calc A . R C4B C 0.7749(11) 0.3756(7) 0.4863(6) 0.0266(18) Uani 0.633(13) 1 d A 1 . C24B C 0.5497(12) 0.7158(8) 0.2543(9) 0.047(3) Uiso 0.633(13) 1 d A 1 . H24B H 0.4986 0.7125 0.1961 0.057 Uiso 0.633(13) 1 calc A 1 R C31A C 0.610(2) 0.466(2) 0.573(2) 0.068(7) Uani 0.367(13) 1 d A 2 . H31D H 0.5938 0.4844 0.5144 0.103 Uiso 0.367(13) 1 calc A 2 GR H31E H 0.5604 0.5160 0.6284 0.103 Uiso 0.367(13) 1 calc A 2 GR H31F H 0.5756 0.3924 0.5589 0.103 Uiso 0.367(13) 1 calc A 2 GR C3A C 0.884(2) 0.294(2) 0.503(2) 0.029(5) Uani 0.367(13) 1 d A 2 . C5A C 0.868(3) 0.437(3) 0.433(2) 0.026(5) Uani 0.367(13) 1 d A 2 . C14A C 0.8396(18) 0.2577(12) 0.5875(12) 0.027(3) Uiso 0.367(13) 1 d A 2 . H14C H 0.7538 0.2937 0.6174 0.032 Uiso 0.367(13) 1 calc A 2 R H14D H 0.8241 0.1788 0.5628 0.032 Uiso 0.367(13) 1 calc A 2 R C21B C 0.7913(11) 0.5344(7) 0.4330(6) 0.029(2) Uiso 0.633(13) 1 d A 1 . H21C H 0.7508 0.5696 0.4985 0.034 Uiso 0.633(13) 1 calc A 1 R H21D H 0.8767 0.5748 0.4312 0.034 Uiso 0.633(13) 1 calc A 1 R O2B O 0.9177(8) 0.2811(5) 0.6447(5) 0.0304(17) Uiso 0.633(13) 1 d A 1 . O3A O 0.7301(16) 0.5441(11) 0.3661(10) 0.037(4) Uiso 0.367(13) 1 d A 2 . C22A C 0.6739(17) 0.6455(13) 0.3693(11) 0.023(4) Uiso 0.367(13) 1 d A 2 . C27A C 0.7005(16) 0.7413(10) 0.4479(13) 0.023(4) Uiso 0.367(13) 1 d A 2 . H27A H 0.7548 0.7419 0.5040 0.027 Uiso 0.367(13) 1 calc A 2 R C26A C 0.6479(13) 0.8369(10) 0.4451(11) 0.022(3) Uiso 0.367(13) 1 d A 2 . H26A H 0.6631 0.9020 0.5005 0.026 Uiso 0.367(13) 1 calc A 2 R C25A C 0.5736(11) 0.8376(9) 0.3619(9) 0.017(3) Uiso 0.367(13) 1 d A 2 . C24A C 0.5477(13) 0.7443(10) 0.2813(10) 0.021(3) Uiso 0.367(13) 1 d A 2 . H24A H 0.4998 0.7458 0.2236 0.025 Uiso 0.367(13) 1 calc A 2 R C23A C 0.5935(15) 0.6466(12) 0.2860(12) 0.023(4) Uiso 0.367(13) 1 d A 2 . H23A H 0.5704 0.5809 0.2330 0.028 Uiso 0.367(13) 1 calc A 2 R Cl3A Cl 0.511(3) 0.9527(19) 0.3506(17) 0.061(3) Uani 0.367(13) 1 d 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 Cl2 0.0581(9) 0.0535(9) 0.0402(7) 0.0263(6) 0.0083(6) 0.0100(7) Cl1 0.0306(6) 0.0710(10) 0.0519(8) 0.0205(7) 0.0092(6) 0.0136(6) Cl3B 0.044(4) 0.072(7) 0.175(11) 0.093(7) -0.030(6) -0.008(4) C9 0.024(2) 0.036(3) 0.033(2) 0.012(2) -0.0001(18) -0.0049(19) C8 0.027(2) 0.028(2) 0.034(2) 0.0116(19) 0.0020(18) -0.0014(18) C15 0.046(3) 0.025(2) 0.042(3) 0.018(2) 0.020(2) 0.009(2) C19 0.031(2) 0.044(3) 0.051(3) 0.030(3) 0.010(2) 0.006(2) C18 0.040(3) 0.031(2) 0.036(2) 0.015(2) 0.013(2) 0.010(2) C10 0.032(2) 0.036(3) 0.030(2) 0.011(2) 0.0047(19) 0.001(2) C12 0.026(2) 0.042(3) 0.041(3) 0.015(2) -0.005(2) -0.006(2) C13 0.036(3) 0.034(3) 0.033(2) 0.005(2) -0.003(2) -0.001(2) C20 0.036(3) 0.040(3) 0.051(3) 0.029(2) 0.011(2) 0.007(2) C11 0.027(2) 0.041(3) 0.040(3) 0.020(2) 0.0065(19) 0.007(2) C16 0.052(3) 0.033(3) 0.043(3) 0.013(2) 0.015(2) -0.010(2) O1 0.0244(16) 0.0297(17) 0.0358(17) 0.0039(14) 0.0005(13) -0.0010(13) C2 0.034(2) 0.020(2) 0.037(2) 0.0135(19) 0.0053(19) 0.0030(18) C1 0.029(2) 0.027(2) 0.032(2) 0.0105(19) 0.0018(18) 0.0011(18) C28 0.030(2) 0.027(2) 0.038(2) 0.015(2) 0.0049(19) 0.0097(19) C7 0.024(2) 0.030(2) 0.034(2) 0.0091(19) 0.0017(18) -0.0001(18) C32 0.035(3) 0.040(3) 0.040(3) 0.022(2) 0.002(2) -0.001(2) C6 0.041(3) 0.028(2) 0.033(2) 0.017(2) 0.005(2) 0.001(2) C33 0.050(3) 0.054(4) 0.037(3) 0.018(3) 0.000(2) 0.005(3) C3B 0.017(6) 0.027(5) 0.030(5) 0.017(4) 0.006(5) 0.006(5) C29 0.045(3) 0.027(3) 0.051(3) 0.013(2) 0.004(2) 0.006(2) C5B 0.036(8) 0.018(7) 0.028(7) 0.011(5) -0.005(5) -0.001(5) C4A 0.020(7) 0.023(7) 0.033(7) 0.012(6) 0.003(6) -0.002(6) C30A 0.040(8) 0.027(7) 0.027(7) 0.009(5) 0.003(6) -0.001(6) C30B 0.026(5) 0.027(4) 0.043(5) 0.014(4) 0.002(4) 0.006(3) C31B 0.041(5) 0.031(4) 0.039(5) 0.007(3) 0.010(4) 0.002(3) C17 0.046(3) 0.041(3) 0.041(3) 0.010(2) 0.003(2) -0.009(2) C4B 0.025(4) 0.018(4) 0.035(4) 0.007(3) 0.002(3) -0.002(3) C31A 0.035(11) 0.072(15) 0.13(2) 0.065(15) 0.041(12) 0.018(10) C3A 0.016(10) 0.033(9) 0.040(10) 0.018(8) -0.003(9) -0.004(9) C5A 0.031(13) 0.019(11) 0.024(10) 0.004(8) -0.007(9) -0.002(9) Cl3A 0.045(5) 0.040(3) 0.113(8) 0.048(5) -0.015(5) 0.001(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 Cl2 C18 1.744(5) . ? Cl1 C11 1.747(5) . ? Cl3B C25B 1.766(17) . ? O2A C15 1.322(11) . ? O2A C14A 1.45(2) . ? C9 H9 0.9500 . ? C9 C8 1.402(7) . ? C9 C10 1.384(7) . ? O3B C22B 1.335(13) . ? O3B C21B 1.424(11) . ? C8 C13 1.376(7) . ? C8 O1 1.369(6) . ? C15 C20 1.383(7) . ? C15 C16 1.398(8) . ? C15 O2B 1.397(7) . ? C19 H19 0.9500 . ? C19 C18 1.387(8) . ? C19 C20 1.387(7) . ? C18 C17 1.390(8) . ? C10 H10 0.9500 . ? C10 C11 1.374(7) . ? C12 H12 0.9500 . ? C12 C13 1.377(7) . ? C12 C11 1.387(8) . ? C13 H13 0.9500 . ? C20 H20 0.9500 . ? C22B C27B 1.379(11) . ? C22B C23B 1.381(11) . ? C27B H27B 0.9500 . ? C27B C26B 1.399(10) . ? C23B H23B 0.9500 . ? C23B C24B 1.377(11) . ? C16 H16 0.9500 . ? C16 C17 1.393(8) . ? C25B C26B 1.392(10) . ? C25B C24B 1.372(11) . ? C26B H26B 0.9500 . ? O1 C7 1.432(5) . ? C2 C1 1.409(6) . ? C2 C28 1.521(6) . ? C2 C3B 1.441(14) . ? C2 C3A 1.34(3) . ? C1 C7 1.503(6) . ? C1 C6 1.410(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.521(7) . ? C21A H21A 0.9900 . ? C21A H21B 0.9900 . ? C21A C5A 1.49(4) . ? C21A O3A 1.43(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C32 C6 1.516(6) . ? C32 C33 1.550(8) . ? C6 C5B 1.42(2) . ? C6 C5A 1.41(3) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C3B C14B 1.498(16) . ? C3B C4B 1.405(16) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C5B C4B 1.43(2) . ? C5B C21B 1.52(2) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C14B O2B 1.473(11) . ? C4A C30A 1.516(19) . ? C4A C3A 1.44(3) . ? C4A C5A 1.42(4) . ? C30A H30A 0.9900 . ? C30A H30B 0.9900 . ? C30A C31A 1.55(3) . ? C30B H30C 0.9900 . ? C30B H30D 0.9900 . ? C30B C31B 1.555(13) . ? C30B C4B 1.502(14) . ? C31B H31A 0.9800 . ? C31B H31B 0.9800 . ? C31B H31C 0.9800 . ? C17 H17 0.9500 . ? C24B H24B 0.9500 . ? C31A H31D 0.9800 . ? C31A H31E 0.9800 . ? C31A H31F 0.9800 . ? C3A C14A 1.56(3) . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? C21B H21C 0.9900 . ? C21B H21D 0.9900 . ? O3A C22A 1.45(2) . ? C22A C27A 1.383(13) . ? C22A C23A 1.418(13) . ? C27A H27A 0.9500 . ? C27A C26A 1.391(12) . ? C26A H26A 0.9500 . ? C26A C25A 1.386(12) . ? C25A C24A 1.375(12) . ? C25A Cl3A 1.72(3) . ? C24A H24A 0.9500 . ? C24A C23A 1.405(12) . ? C23A H23A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O2A C14A 105.2(11) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C10 C9 C8 119.2(4) . . ? C22B O3B C21B 117.8(8) . . ? C13 C8 C9 119.7(4) . . ? O1 C8 C9 124.0(4) . . ? O1 C8 C13 116.3(4) . . ? O2A C15 C20 136.7(9) . . ? O2A C15 C16 103.7(8) . . ? O2A C15 O2B 17.2(6) . . ? C20 C15 C16 119.5(5) . . ? C20 C15 O2B 119.5(6) . . ? O2B C15 C16 121.0(5) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C20 C19 C18 118.8(5) . . ? C19 C18 Cl2 119.3(4) . . ? C19 C18 C17 121.0(5) . . ? C17 C18 Cl2 119.7(4) . . ? C9 C10 H10 120.0 . . ? C11 C10 C9 119.9(5) . . ? C11 C10 H10 120.0 . . ? C13 C12 H12 120.8 . . ? C13 C12 C11 118.4(5) . . ? C11 C12 H12 120.8 . . ? C8 C13 C12 121.4(5) . . ? C8 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C15 C20 C19 121.4(5) . . ? C15 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? O3B C22B C27B 123.9(9) . . ? O3B C22B C23B 114.4(9) . . ? C27B C22B C23B 121.7(10) . . ? C22B C27B H27B 119.9 . . ? C22B C27B C26B 120.2(10) . . ? C26B C27B H27B 119.9 . . ? C22B C23B H23B 121.0 . . ? C24B C23B C22B 118.1(11) . . ? C24B C23B H23B 121.0 . . ? C10 C11 Cl1 119.1(4) . . ? C10 C11 C12 121.4(5) . . ? C12 C11 Cl1 119.4(4) . . ? C15 C16 H16 120.1 . . ? C17 C16 C15 119.7(5) . . ? C17 C16 H16 120.1 . . ? C26B C25B Cl3B 115.8(8) . . ? C24B C25B Cl3B 122.8(8) . . ? C24B C25B C26B 121.5(8) . . ? C27B C26B H26B 121.3 . . ? C25B C26B C27B 117.4(9) . . ? C25B C26B H26B 121.3 . . ? C8 O1 C7 119.3(4) . . ? C1 C2 C28 121.5(4) . . ? C1 C2 C3B 118.5(6) . . ? C3B C2 C28 119.3(6) . . ? C3A C2 C1 119.1(12) . . ? C3A C2 C28 118.1(12) . . ? C3A C2 C3B 20.0(8) . . ? C2 C1 C7 118.0(4) . . ? C2 C1 C6 120.6(4) . . ? C6 C1 C7 121.1(4) . . ? C2 C28 H28A 109.1 . . ? C2 C28 H28B 109.1 . . ? H28A C28 H28B 107.8 . . ? C29 C28 C2 112.5(4) . . ? C29 C28 H28A 109.1 . . ? C29 C28 H28B 109.1 . . ? H21A C21A H21B 108.2 . . ? C5A C21A H21A 109.7 . . ? C5A C21A H21B 109.7 . . ? O3A C21A H21A 109.7 . . ? O3A C21A H21B 109.7 . . ? O3A C21A C5A 109.7(14) . . ? O1 C7 C1 105.8(4) . . ? O1 C7 H7A 110.6 . . ? O1 C7 H7B 110.6 . . ? C1 C7 H7A 110.6 . . ? C1 C7 H7B 110.6 . . ? H7A C7 H7B 108.7 . . ? H32A C32 H32B 108.1 . . ? C6 C32 H32A 109.5 . . ? C6 C32 H32B 109.5 . . ? C6 C32 C33 110.7(4) . . ? C33 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? C1 C6 C32 120.5(4) . . ? C1 C6 C5B 119.0(8) . . ? C5B C6 C32 119.9(8) . . ? C5A C6 C1 120.2(14) . . ? C5A C6 C32 118.2(14) . . ? C5A C6 C5B 19.3(8) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 C3B C14B 119.1(10) . . ? C4B C3B C2 121.7(10) . . ? C4B C3B C14B 119.0(10) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C6 C5B C4B 121.9(14) . . ? C6 C5B C21B 120.0(12) . . ? C4B C5B C21B 117.5(14) . . ? C3B C14B H14A 110.6 . . ? C3B C14B H14B 110.6 . . ? H14A C14B H14B 108.7 . . ? O2B C14B C3B 105.8(8) . . ? O2B C14B H14A 110.6 . . ? O2B C14B H14B 110.6 . . ? C3A C4A C30A 120.8(15) . . ? C5A C4A C30A 119.6(17) . . ? C5A C4A C3A 120(2) . . ? C4A C30A H30A 110.2 . . ? C4A C30A H30B 110.2 . . ? C4A C30A C31A 107.7(16) . . ? H30A C30A H30B 108.5 . . ? C31A C30A H30A 110.2 . . ? C31A C30A H30B 110.2 . . ? H30C C30B H30D 107.4 . . ? C31B C30B H30C 108.2 . . ? C31B C30B H30D 108.2 . . ? C4B C30B H30C 108.2 . . ? C4B C30B H30D 108.2 . . ? C4B C30B C31B 116.1(9) . . ? C18 C17 C16 119.6(5) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C3B C4B C5B 117.3(11) . . ? C3B C4B C30B 121.1(8) . . ? C5B C4B C30B 121.6(10) . . ? C23B C24B H24B 119.5 . . ? C25B C24B C23B 121.1(10) . . ? C25B C24B H24B 119.5 . . ? C30A C31A H31D 109.5 . . ? C30A C31A H31E 109.5 . . ? C30A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 109.5 . . ? C2 C3A C4A 122(2) . . ? C2 C3A C14A 122(2) . . ? C4A C3A C14A 116(2) . . ? C6 C5A C21A 119(2) . . ? C6 C5A C4A 117(2) . . ? C4A C5A C21A 123(3) . . ? O2A C14A C3A 103.5(12) . . ? O2A C14A H14C 111.1 . . ? O2A C14A H14D 111.1 . . ? C3A C14A H14C 111.1 . . ? C3A C14A H14D 111.1 . . ? H14C C14A H14D 109.0 . . ? O3B C21B C5B 109.1(8) . . ? O3B C21B H21C 109.9 . . ? O3B C21B H21D 109.9 . . ? C5B C21B H21C 109.9 . . ? C5B C21B H21D 109.9 . . ? H21C C21B H21D 108.3 . . ? C15 O2B C14B 121.9(6) . . ? C21A O3A C22A 117.1(13) . . ? C27A C22A O3A 122.8(12) . . ? C27A C22A C23A 119.0(14) . . ? C23A C22A O3A 118.2(12) . . ? C22A C27A H27A 119.9 . . ? C22A C27A C26A 120.2(14) . . ? C26A C27A H27A 119.9 . . ? C27A C26A H26A 119.8 . . ? C25A C26A C27A 120.4(12) . . ? C25A C26A H26A 119.8 . . ? C26A C25A Cl3A 123.2(12) . . ? C24A C25A C26A 121.1(10) . . ? C24A C25A Cl3A 115.7(12) . . ? C25A C24A H24A 120.6 . . ? C25A C24A C23A 118.8(11) . . ? C23A C24A H24A 120.6 . . ? C22A C23A H23A 119.8 . . ? C24A C23A C22A 120.4(13) . . ? C24A C23A H23A 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 C18 C17 C16 177.7(4) . . . . ? Cl3B C25B C26B C27B 179.7(9) . . . . ? Cl3B C25B C24B C23B 179.8(10) . . . . ? O2A C15 C20 C19 177.5(9) . . . . ? O2A C15 C16 C17 -178.5(7) . . . . ? O2A C15 O2B C14B 168(3) . . . . ? C9 C8 C13 C12 -0.5(8) . . . . ? C9 C8 O1 C7 -0.7(7) . . . . ? C9 C10 C11 Cl1 -179.1(4) . . . . ? C9 C10 C11 C12 1.6(8) . . . . ? O3B C22B C27B C26B -175.6(10) . . . . ? O3B C22B C23B C24B 175.4(10) . . . . ? C8 C9 C10 C11 -2.2(7) . . . . ? C8 O1 C7 C1 175.8(4) . . . . ? C15 O2A C14A C3A -170.2(14) . . . . ? C15 C16 C17 C18 1.0(8) . . . . ? C19 C18 C17 C16 -1.3(8) . . . . ? C18 C19 C20 C15 -0.4(8) . . . . ? C10 C9 C8 C13 1.7(7) . . . . ? C10 C9 C8 O1 -177.2(4) . . . . ? C13 C8 O1 C7 -179.5(4) . . . . ? C13 C12 C11 Cl1 -179.7(4) . . . . ? C13 C12 C11 C10 -0.3(8) . . . . ? C20 C15 C16 C17 -0.4(8) . . . . ? C20 C15 O2B C14B -11.1(9) . . . . ? C20 C19 C18 Cl2 -177.9(4) . . . . ? C20 C19 C18 C17 1.0(8) . . . . ? C22B O3B C21B C5B -171.3(11) . . . . ? C22B C27B C26B C25B -0.2(16) . . . . ? C22B C23B C24B C25B 1.2(17) . . . . ? C27B C22B C23B C24B -2.0(18) . . . . ? C23B C22B C27B C26B 1.5(18) . . . . ? C11 C12 C13 C8 -0.2(8) . . . . ? C16 C15 C20 C19 0.1(8) . . . . ? C16 C15 O2B C14B 166.7(6) . . . . ? C26B C25B C24B C23B 0.1(16) . . . . ? O1 C8 C13 C12 178.5(5) . . . . ? C2 C1 C7 O1 -83.3(5) . . . . ? C2 C1 C6 C32 -178.0(5) . . . . ? C2 C1 C6 C5B -7.7(9) . . . . ? C2 C1 C6 C5A 14.5(12) . . . . ? C2 C3B C14B O2B 75.1(11) . . . . ? C2 C3B C4B C5B -3.8(16) . . . . ? C2 C3B C4B C30B 174.9(10) . . . . ? C2 C3A C14A O2A 96.4(17) . . . . ? C1 C2 C28 C29 -91.1(6) . . . . ? C1 C2 C3B C14B -179.8(8) . . . . ? C1 C2 C3B C4B -5.6(13) . . . . ? C1 C2 C3A C4A 6.3(19) . . . . ? C1 C2 C3A C14A 177.2(11) . . . . ? C1 C6 C5B C4B -2.2(14) . . . . ? C1 C6 C5B C21B 168.6(8) . . . . ? C1 C6 C5A C21A 170.0(12) . . . . ? C1 C6 C5A C4A -12(2) . . . . ? C28 C2 C1 C7 -4.2(7) . . . . ? C28 C2 C1 C6 -177.9(5) . . . . ? C28 C2 C3B C14B 9.4(13) . . . . ? C28 C2 C3B C4B -176.4(8) . . . . ? C28 C2 C3A C4A 173.3(12) . . . . ? C28 C2 C3A C14A -15.8(19) . . . . ? C21A O3A C22A C27A -12(2) . . . . ? C21A O3A C22A C23A 164.8(14) . . . . ? C7 C1 C6 C32 8.4(7) . . . . ? C7 C1 C6 C5B 178.8(7) . . . . ? C7 C1 C6 C5A -159.0(11) . . . . ? C32 C6 C5B C4B 168.2(8) . . . . ? C32 C6 C5B C21B -21.0(13) . . . . ? C32 C6 C5A C21A 2(2) . . . . ? C32 C6 C5A C4A -179.8(12) . . . . ? C6 C1 C7 O1 90.4(5) . . . . ? C6 C5B C4B C3B 7.8(16) . . . . ? C6 C5B C4B C30B -170.9(10) . . . . ? C6 C5B C21B O3B 79.5(11) . . . . ? C33 C32 C6 C1 85.6(6) . . . . ? C33 C32 C6 C5B -84.7(8) . . . . ? C33 C32 C6 C5A -106.7(11) . . . . ? C3B C2 C1 C7 -174.8(7) . . . . ? C3B C2 C1 C6 11.5(9) . . . . ? C3B C2 C28 C29 79.4(8) . . . . ? C3B C2 C3A C4A -88(5) . . . . ? C3B C2 C3A C14A 83(5) . . . . ? C3B C14B O2B C15 -169.0(8) . . . . ? C5B C6 C5A C21A -98(6) . . . . ? C5B C6 C5A C4A 80(6) . . . . ? C14B C3B C4B C5B 170.3(10) . . . . ? C14B C3B C4B C30B -11.0(15) . . . . ? C4A C3A C14A O2A -92.2(16) . . . . ? C30A C4A C3A C2 176.2(15) . . . . ? C30A C4A C3A C14A 5(2) . . . . ? C30A C4A C5A C21A 4(3) . . . . ? C30A C4A C5A C6 -173.5(15) . . . . ? C31B C30B C4B C3B 82.2(12) . . . . ? C31B C30B C4B C5B -99.1(11) . . . . ? C4B C3B C14B O2B -99.2(10) . . . . ? C4B C5B C21B O3B -109.3(11) . . . . ? C24B C25B C26B C27B -0.6(15) . . . . ? C3A C2 C1 C7 162.3(10) . . . . ? C3A C2 C1 C6 -11.4(12) . . . . ? C3A C2 C28 C29 102.2(10) . . . . ? C3A C2 C3B C14B -83(5) . . . . ? C3A C2 C3B C4B 91(5) . . . . ? C3A C4A C30A C31A -100.0(17) . . . . ? C3A C4A C5A C21A -175.2(16) . . . . ? C3A C4A C5A C6 7(2) . . . . ? C5A C21A O3A C22A 172.1(18) . . . . ? C5A C6 C5B C4B -101(6) . . . . ? C5A C6 C5B C21B 69(6) . . . . ? C5A C4A C30A C31A 80.5(19) . . . . ? C5A C4A C3A C2 -4(2) . . . . ? C5A C4A C3A C14A -175.7(16) . . . . ? C14A O2A C15 C20 -6.9(15) . . . . ? C14A O2A C15 C16 170.8(8) . . . . ? C14A O2A C15 O2B -7.9(19) . . . . ? C21B O3B C22B C27B -15.0(16) . . . . ? C21B O3B C22B C23B 167.6(9) . . . . ? C21B C5B C4B C3B -163.2(10) . . . . ? C21B C5B C4B C30B 18.1(15) . . . . ? O2B C15 C20 C19 177.9(5) . . . . ? O2B C15 C16 C17 -178.1(5) . . . . ? O3A C21A C5A C6 64(2) . . . . ? O3A C21A C5A C4A -113.5(18) . . . . ? O3A C22A C27A C26A 177.5(15) . . . . ? O3A C22A C23A C24A -173.9(14) . . . . ? C22A C27A C26A C25A -3(2) . . . . ? C27A C22A C23A C24A 3(2) . . . . ? C27A C26A C25A C24A 1(2) . . . . ? C27A C26A C25A Cl3A -177.3(15) . . . . ? C26A C25A C24A C23A 2.4(19) . . . . ? C25A C24A C23A C22A -5(2) . . . . ? C23A C22A C27A C26A 0(2) . . . . ? Cl3A C25A C24A C23A -178.9(14) . . . . ? # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.007 0.000 0.000 351 35 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 962424'