# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Duncan Bruce' 'Carsten Prasang' 'Adrian C. Whitwood' _publ_contact_author_name 'Duncan Bruce' _publ_contact_author_address ; Department of Chemistry University of York Heslington York YO10 5DD UNITED KINGDOM ; _publ_contact_author_email DB519@YORK.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Chirality from nowhere: spontaneous symmetry breaking in halogen-bonded, bent-core liquid crystals and observation of a Iso-N-N* phase sequence ; data_dwb0617m _database_code_depnum_ccdc_archive 'CCDC 671520' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '8(C19 H23 N O), 2(C4 H8 O), C4 H8 O, 4(C6 F4 I2)' _chemical_formula_sum 'C188 H208 F16 I8 N8 O11' _chemical_formula_weight 4074.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.217(5) _cell_length_b 14.835(9) _cell_length_c 32.431(19) _cell_angle_alpha 89.206(12) _cell_angle_beta 82.332(12) _cell_angle_gamma 89.607(12) _cell_volume 4394(5) _cell_formula_units_Z 1 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5348 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.07 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 1.490 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.145 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16353 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0884 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 0.63 _diffrn_reflns_theta_max 25.17 _reflns_number_total 12876 _reflns_number_gt 9342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1377P)^2^+140.2920P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12876 _refine_ls_number_parameters 1067 _refine_ls_number_restraints 724 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.1001 _refine_ls_wR_factor_ref 0.2854 _refine_ls_wR_factor_gt 0.2702 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1421(16) 0.4518(9) 0.8746(5) 0.020(3) Uani 1 1 d U . . H1 H 1.2238 0.4454 0.8894 0.024 Uiso 1 1 calc R . . C2 C 1.0553(16) 0.5290(9) 0.8810(5) 0.019(3) Uani 1 1 d U . . H2 H 1.0765 0.5724 0.9006 0.022 Uiso 1 1 calc R . . C3 C 0.9376(15) 0.5429(8) 0.8588(4) 0.014(3) Uani 1 1 d U . . C4 C 0.9119(17) 0.4749(8) 0.8323(5) 0.018(3) Uani 1 1 d U . . H4 H 0.8318 0.4795 0.8168 0.022 Uiso 1 1 calc R . . C5 C 1.0043(16) 0.3981(9) 0.8282(5) 0.019(3) Uani 1 1 d U . . H5 H 0.9843 0.3522 0.8096 0.023 Uiso 1 1 calc R . . C6 C 0.8398(16) 0.6195(9) 0.8634(4) 0.017(3) Uani 1 1 d U . . H6 H 0.7548 0.6171 0.8498 0.020 Uiso 1 1 calc R . . C7 C 0.8583(16) 0.6938(8) 0.8851(4) 0.015(3) Uani 1 1 d U . . H7 H 0.9439 0.6965 0.8984 0.018 Uiso 1 1 calc R . . C8 C 0.7574(16) 0.7718(8) 0.8901(5) 0.018(3) Uani 1 1 d U . . C9 C 0.6349(17) 0.7799(10) 0.8688(5) 0.023(3) Uani 1 1 d U . . H9 H 0.6162 0.7352 0.8496 0.028 Uiso 1 1 calc R . . C10 C 0.5407(16) 0.8537(8) 0.8760(4) 0.015(3) Uani 1 1 d U . . H10 H 0.4571 0.8580 0.8618 0.018 Uiso 1 1 calc R . . C11 C 0.5666(16) 0.9204(9) 0.9032(5) 0.019(3) Uani 1 1 d U . . C12 C 0.6879(16) 0.9145(8) 0.9236(4) 0.016(3) Uani 1 1 d U . . H12 H 0.7079 0.9606 0.9421 0.019 Uiso 1 1 calc R . . C13 C 0.7821(17) 0.8395(9) 0.9169(5) 0.022(3) Uani 1 1 d U . . H13 H 0.8653 0.8355 0.9312 0.026 Uiso 1 1 calc R . . C14 C 0.4847(15) 1.0585(8) 0.9364(4) 0.015(3) Uani 1 1 d U . . H14A H 0.5765 1.0910 0.9265 0.018 Uiso 1 1 calc R . . H14B H 0.4912 1.0337 0.9646 0.018 Uiso 1 1 calc R . . C15 C 0.3529(16) 1.1219(9) 0.9371(5) 0.020(3) Uani 1 1 d U . . H15A H 0.3451 1.1436 0.9085 0.024 Uiso 1 1 calc R . . H15B H 0.2623 1.0886 0.9474 0.024 Uiso 1 1 calc R . . C16 C 0.3679(16) 1.2019(8) 0.9649(4) 0.016(3) Uani 1 1 d U . . H16A H 0.4587 1.2348 0.9543 0.019 Uiso 1 1 calc R . . H16B H 0.3775 1.1795 0.9933 0.019 Uiso 1 1 calc R . . C17 C 0.2379(16) 1.2674(8) 0.9671(5) 0.018(3) Uani 1 1 d U . . H17A H 0.2275 1.2892 0.9387 0.022 Uiso 1 1 calc R . . H17B H 0.1473 1.2347 0.9780 0.022 Uiso 1 1 calc R . . C18 C 0.2541(16) 1.3478(8) 0.9945(5) 0.019(3) Uani 1 1 d U . . H18A H 0.3434 1.3814 0.9832 0.023 Uiso 1 1 calc R . . H18B H 0.2668 1.3259 1.0228 0.023 Uiso 1 1 calc R . . C19 C 0.1222(17) 1.4118(10) 0.9974(5) 0.028(4) Uani 1 1 d U . . H19A H 0.1017 1.4279 0.9694 0.042 Uiso 1 1 calc R . . H19B H 0.1439 1.4666 1.0120 0.042 Uiso 1 1 calc R . . H19C H 0.0366 1.3820 1.0128 0.042 Uiso 1 1 calc R . . N1 N 1.1170(13) 0.3872(7) 0.8490(4) 0.017(3) Uani 1 1 d U . . O1 O 0.4612(11) 0.9873(6) 0.9082(3) 0.021(2) Uani 1 1 d U . . C20 C 1.022(2) 0.8691(11) 0.5891(6) 0.039(4) Uani 1 1 d U . . H20 H 1.1223 0.8825 0.5804 0.046 Uiso 1 1 calc R . . C21 C 0.943(2) 0.8215(11) 0.5615(6) 0.036(4) Uani 1 1 d U . . H21 H 0.9906 0.8047 0.5349 0.043 Uiso 1 1 calc R . . C22 C 0.8023(19) 0.8002(10) 0.5732(5) 0.030(4) Uani 1 1 d U . . C23 C 0.741(2) 0.8287(11) 0.6125(5) 0.033(4) Uani 1 1 d U . . H23 H 0.6416 0.8154 0.6220 0.039 Uiso 1 1 calc R . . C24 C 0.820(2) 0.8750(11) 0.6378(6) 0.037(4) Uani 1 1 d U . . H24 H 0.7735 0.8933 0.6644 0.044 Uiso 1 1 calc R . . C25 C 0.711(2) 0.7508(10) 0.5483(5) 0.033(4) Uani 1 1 d U . . H25 H 0.6180 0.7319 0.5616 0.039 Uiso 1 1 calc R . . C26 C 0.746(2) 0.7295(11) 0.5083(6) 0.038(4) Uani 1 1 d U . . H26 H 0.8392 0.7488 0.4951 0.045 Uiso 1 1 calc R . . C27 C 0.6578(19) 0.6806(10) 0.4834(5) 0.029(4) Uani 1 1 d U . . C28 C 0.527(2) 0.6399(13) 0.4993(6) 0.046(5) Uani 1 1 d U . . H28 H 0.4948 0.6446 0.5283 0.055 Uiso 1 1 calc R . . C29 C 0.444(3) 0.5940(14) 0.4758(6) 0.054(5) Uani 1 1 d U . . H29 H 0.3572 0.5651 0.4886 0.065 Uiso 1 1 calc R . . C30 C 0.483(2) 0.5887(11) 0.4335(5) 0.034(4) Uani 1 1 d U . . C31 C 0.610(2) 0.6286(13) 0.4155(6) 0.046(5) Uani 1 1 d U . . H31 H 0.6415 0.6217 0.3866 0.056 Uiso 1 1 calc R . . C32 C 0.698(2) 0.6814(12) 0.4405(6) 0.041(4) Uani 1 1 d U . . H32 H 0.7792 0.7153 0.4279 0.049 Uiso 1 1 calc R . . C33 C 0.431(2) 0.5204(11) 0.3701(5) 0.036(4) Uani 1 1 d U . . H33A H 0.5330 0.4981 0.3653 0.043 Uiso 1 1 calc R . . H33B H 0.4232 0.5752 0.3527 0.043 Uiso 1 1 calc R . . C34 C 0.329(2) 0.4498(11) 0.3591(5) 0.035(4) Uani 1 1 d U . . H34A H 0.2265 0.4699 0.3677 0.042 Uiso 1 1 calc R . . H34B H 0.3447 0.3936 0.3747 0.042 Uiso 1 1 calc R . . C35 C 0.349(2) 0.4302(11) 0.3128(5) 0.034(4) Uani 1 1 d U . . H35A H 0.3296 0.4860 0.2973 0.040 Uiso 1 1 calc R . . H35B H 0.4520 0.4121 0.3040 0.040 Uiso 1 1 calc R . . C36 C 0.249(2) 0.3566(11) 0.3018(5) 0.034(4) Uani 1 1 d U . . H36A H 0.2624 0.3031 0.3195 0.041 Uiso 1 1 calc R . . H36B H 0.1466 0.3773 0.3087 0.041 Uiso 1 1 calc R . . C37 C 0.273(2) 0.3288(12) 0.2574(5) 0.038(4) Uani 1 1 d U . . H37A H 0.3761 0.3094 0.2503 0.045 Uiso 1 1 calc R . . H37B H 0.2572 0.3820 0.2397 0.045 Uiso 1 1 calc R . . C38 C 0.1758(18) 0.2542(10) 0.2469(5) 0.027(4) Uani 1 1 d U . . H38A H 0.1892 0.2014 0.2645 0.041 Uiso 1 1 calc R . . H38B H 0.2013 0.2385 0.2176 0.041 Uiso 1 1 calc R . . H38C H 0.0734 0.2741 0.2518 0.041 Uiso 1 1 calc R . . N2 N 0.9617(16) 0.8956(9) 0.6263(4) 0.034(3) Uani 1 1 d U . . O2 O 0.3906(15) 0.5406(9) 0.4127(4) 0.047(3) Uani 1 1 d U . . C39 C 0.084(2) 0.6726(11) 0.3711(6) 0.036(4) Uani 1 1 d U . . H39 H 0.1179 0.6122 0.3676 0.043 Uiso 1 1 calc R . . C40 C 0.137(2) 0.7241(10) 0.4006(5) 0.032(4) Uani 1 1 d U . . H40 H 0.2091 0.6997 0.4160 0.038 Uiso 1 1 calc R . . C41 C 0.0864(18) 0.8118(10) 0.4082(5) 0.024(3) Uani 1 1 d U . . C42 C -0.0165(18) 0.8424(10) 0.3824(5) 0.028(4) Uani 1 1 d U . . H42 H -0.0564 0.9015 0.3857 0.034 Uiso 1 1 calc R . . C43 C -0.058(2) 0.7885(11) 0.3530(6) 0.035(4) Uani 1 1 d U . . H43 H -0.1247 0.8124 0.3355 0.042 Uiso 1 1 calc R . . C44 C 0.135(2) 0.8703(11) 0.4388(5) 0.032(4) Uani 1 1 d U . . H44 H 0.0934 0.9290 0.4407 0.039 Uiso 1 1 calc R . . C45 C 0.2306(19) 0.8514(11) 0.4644(5) 0.031(4) Uani 1 1 d U . . H45 H 0.2745 0.7933 0.4619 0.037 Uiso 1 1 calc R . . C46 C 0.2768(17) 0.9087(9) 0.4958(5) 0.024(3) Uani 1 1 d U . . C47 C 0.2192(19) 0.9970(10) 0.5035(5) 0.029(4) Uani 1 1 d U . . H47 H 0.1513 1.0208 0.4865 0.035 Uiso 1 1 calc R . . C48 C 0.258(2) 1.0474(12) 0.5341(6) 0.038(4) Uani 1 1 d U . . H48 H 0.2145 1.1050 0.5394 0.046 Uiso 1 1 calc R . . C49 C 0.3637(19) 1.0159(10) 0.5583(5) 0.031(4) Uani 1 1 d U . . C50 C 0.4228(19) 0.9298(11) 0.5512(5) 0.032(4) Uani 1 1 d U . . H50 H 0.4912 0.9055 0.5679 0.038 Uiso 1 1 calc R . . C51 C 0.379(2) 0.8808(11) 0.5192(5) 0.035(4) Uani 1 1 d U . . H51 H 0.4235 0.8237 0.5133 0.042 Uiso 1 1 calc R . . C52 C 0.4988(18) 1.0402(10) 0.6146(5) 0.027(4) Uani 1 1 d U . . H52A H 0.5936 1.0239 0.5983 0.032 Uiso 1 1 calc R . . H52B H 0.4588 0.9864 0.6306 0.032 Uiso 1 1 calc R . . C53 C 0.5172(17) 1.1170(10) 0.6433(5) 0.024(3) Uani 1 1 d U . . H53A H 0.4220 1.1306 0.6601 0.029 Uiso 1 1 calc R . . H53B H 0.5488 1.1714 0.6266 0.029 Uiso 1 1 calc R . . C54 C 0.6298(18) 1.0941(10) 0.6722(5) 0.025(3) Uani 1 1 d U . . H54A H 0.5996 1.0383 0.6881 0.030 Uiso 1 1 calc R . . H54B H 0.7255 1.0822 0.6553 0.030 Uiso 1 1 calc R . . C55 C 0.6476(18) 1.1690(10) 0.7025(5) 0.025(3) Uani 1 1 d U . . H55A H 0.5522 1.1796 0.7198 0.030 Uiso 1 1 calc R . . H55B H 0.6744 1.2251 0.6865 0.030 Uiso 1 1 calc R . . C56 C 0.7628(18) 1.1495(11) 0.7312(5) 0.029(4) Uani 1 1 d U . . H56A H 0.7318 1.0964 0.7489 0.035 Uiso 1 1 calc R . . H56B H 0.8563 1.1340 0.7140 0.035 Uiso 1 1 calc R . . C57 C 0.788(2) 1.2268(12) 0.7587(6) 0.038(4) Uani 1 1 d U . . H57A H 0.8171 1.2802 0.7415 0.056 Uiso 1 1 calc R . . H57B H 0.8661 1.2108 0.7754 0.056 Uiso 1 1 calc R . . H57C H 0.6978 1.2399 0.7773 0.056 Uiso 1 1 calc R . . N3 N -0.0123(16) 0.7038(9) 0.3471(4) 0.033(3) Uani 1 1 d U . . O3 O 0.3968(13) 1.0738(7) 0.5876(4) 0.033(3) Uani 1 1 d U . . C58 C -0.1416(17) 1.0481(9) 0.1320(5) 0.021(3) Uani 1 1 d U . . H58 H -0.2245 1.0550 0.1177 0.025 Uiso 1 1 calc R . . C59 C -0.0511(16) 0.9751(9) 0.1217(5) 0.018(3) Uani 1 1 d U . . H59 H -0.0676 0.9366 0.0996 0.021 Uiso 1 1 calc R . . C60 C 0.0653(16) 0.9587(8) 0.1444(4) 0.015(3) Uani 1 1 d U . . C61 C 0.0872(17) 1.0219(9) 0.1745(5) 0.020(3) Uani 1 1 d U . . H61 H 0.1675 1.0165 0.1899 0.023 Uiso 1 1 calc R . . C62 C -0.0131(16) 1.0935(9) 0.1812(5) 0.020(3) Uani 1 1 d U . . H62 H -0.0005 1.1340 0.2029 0.024 Uiso 1 1 calc R . . C63 C 0.1676(17) 0.8832(9) 0.1370(4) 0.019(3) Uani 1 1 d U . . H63 H 0.2548 0.8854 0.1496 0.023 Uiso 1 1 calc R . . C64 C 0.1484(16) 0.8111(8) 0.1140(4) 0.015(3) Uani 1 1 d U . . H64 H 0.0630 0.8096 0.1005 0.018 Uiso 1 1 calc R . . C65 C 0.2516(16) 0.7331(9) 0.1079(4) 0.018(3) Uani 1 1 d U . . C66 C 0.3757(16) 0.7239(8) 0.1266(5) 0.017(3) Uani 1 1 d U . . H66 H 0.3980 0.7697 0.1450 0.020 Uiso 1 1 calc R . . C67 C 0.4698(16) 0.6514(9) 0.1201(5) 0.019(3) Uani 1 1 d U . . H67 H 0.5547 0.6474 0.1337 0.023 Uiso 1 1 calc R . . C68 C 0.4379(16) 0.5838(8) 0.0931(5) 0.017(3) Uani 1 1 d U . . C69 C 0.3146(16) 0.5904(9) 0.0739(4) 0.018(3) Uani 1 1 d U . . H69 H 0.2917 0.5444 0.0558 0.022 Uiso 1 1 calc R . . C70 C 0.2218(17) 0.6660(9) 0.0812(5) 0.021(3) Uani 1 1 d U . . H70 H 0.1372 0.6709 0.0675 0.025 Uiso 1 1 calc R . . C71 C 0.5119(15) 0.4410(8) 0.0636(4) 0.015(3) Uani 1 1 d U . . H71A H 0.5007 0.4625 0.0351 0.018 Uiso 1 1 calc R . . H71B H 0.4209 0.4098 0.0754 0.018 Uiso 1 1 calc R . . C72 C 0.6416(17) 0.3775(9) 0.0624(5) 0.022(3) Uani 1 1 d U . . H72A H 0.6538 0.3587 0.0911 0.026 Uiso 1 1 calc R . . H72B H 0.7315 0.4096 0.0503 0.026 Uiso 1 1 calc R . . C73 C 0.6225(15) 0.2942(8) 0.0367(4) 0.014(3) Uani 1 1 d U . . H73A H 0.6095 0.3132 0.0081 0.017 Uiso 1 1 calc R . . H73B H 0.5329 0.2620 0.0489 0.017 Uiso 1 1 calc R . . C74 C 0.7546(17) 0.2295(9) 0.0351(5) 0.021(3) Uani 1 1 d U . . H74A H 0.8448 0.2626 0.0242 0.025 Uiso 1 1 calc R . . H74B H 0.7647 0.2084 0.0637 0.025 Uiso 1 1 calc R . . C75 C 0.7396(17) 0.1494(8) 0.0082(5) 0.022(3) Uani 1 1 d U . . H75A H 0.7246 0.1707 -0.0200 0.026 Uiso 1 1 calc R . . H75B H 0.6518 0.1148 0.0199 0.026 Uiso 1 1 calc R . . C76 C 0.8729(18) 0.0871(9) 0.0047(5) 0.028(4) Uani 1 1 d U . . H76A H 0.9576 0.1184 -0.0104 0.041 Uiso 1 1 calc R . . H76B H 0.8530 0.0328 -0.0104 0.041 Uiso 1 1 calc R . . H76C H 0.8940 0.0702 0.0326 0.041 Uiso 1 1 calc R . . N4 N -0.1234(14) 1.1091(8) 0.1600(4) 0.024(3) Uani 1 1 d U . . O4 O 0.5389(11) 0.5157(6) 0.0892(3) 0.019(2) Uani 1 1 d U . . C77 C 0.3054(16) 0.0991(9) 0.7853(4) 0.018(3) Uani 1 1 d U . . C78 C 0.2269(16) 0.0689(9) 0.7557(4) 0.016(3) Uani 1 1 d U . . C79 C 0.2568(17) -0.0096(9) 0.7323(4) 0.018(3) Uani 1 1 d U . . C80 C 0.3787(18) -0.0582(9) 0.7415(5) 0.022(3) Uani 1 1 d U . . C81 C 0.4650(17) -0.0334(9) 0.7708(5) 0.022(3) Uani 1 1 d U . . C82 C 0.4249(17) 0.0465(9) 0.7926(5) 0.019(3) Uani 1 1 d U . . F1 F 0.1100(10) 0.1180(5) 0.7475(3) 0.029(2) Uani 1 1 d U . . F2 F 0.4209(10) -0.1325(6) 0.7199(3) 0.034(2) Uani 1 1 d U . . F3 F 0.5815(10) -0.0782(6) 0.7772(3) 0.031(2) Uani 1 1 d U . . F4 F 0.5098(9) 0.0733(6) 0.8202(3) 0.026(2) Uani 1 1 d U . . I1 I 0.24804(10) 0.21955(6) 0.81660(3) 0.0200(3) Uani 1 1 d U . . I2 I 0.13195(12) -0.04900(6) 0.68780(3) 0.0265(3) Uani 1 1 d U . . C83 C 0.7297(18) 0.5339(9) 0.2538(4) 0.020(3) Uani 1 1 d U . . C84 C 0.7702(16) 0.4506(9) 0.2364(5) 0.019(3) Uani 1 1 d U . . C85 C 0.6951(15) 0.4077(9) 0.2094(4) 0.013(3) Uani 1 1 d U . . C86 C 0.5652(17) 0.4497(9) 0.2001(5) 0.020(3) Uani 1 1 d U . . C87 C 0.5201(15) 0.5313(8) 0.2171(4) 0.013(3) Uani 1 1 d U . . C88 C 0.5955(18) 0.5704(9) 0.2448(5) 0.022(3) Uani 1 1 d U . . F5 F 0.8960(10) 0.4147(5) 0.2447(3) 0.026(2) Uani 1 1 d U . . F6 F 0.4861(9) 0.4114(5) 0.1743(3) 0.025(2) Uani 1 1 d U . . F7 F 0.3923(10) 0.5666(5) 0.2104(3) 0.029(2) Uani 1 1 d U . . F8 F 0.5410(10) 0.6464(5) 0.2637(3) 0.032(2) Uani 1 1 d U . . I3 I 0.84879(11) 0.60162(6) 0.29401(3) 0.0252(3) Uani 1 1 d U . . I4 I 0.75667(10) 0.28022(6) 0.18604(3) 0.0209(3) Uani 1 1 d U . . C89 C 0.333(3) 0.7234(14) 0.6410(7) 0.057(6) Uani 1 1 d U . . H89A H 0.3098 0.7869 0.6344 0.069 Uiso 1 1 calc R . . H89B H 0.4084 0.7229 0.6600 0.069 Uiso 1 1 calc R . . C90 C 0.201(3) 0.6769(17) 0.6605(8) 0.075(7) Uani 1 1 d U . . H90A H 0.2256 0.6303 0.6805 0.090 Uiso 1 1 calc R . . H90B H 0.1306 0.7202 0.6753 0.090 Uiso 1 1 calc R . . C91 C 0.138(3) 0.6355(16) 0.6262(7) 0.066(6) Uani 1 1 d U . . H91A H 0.0506 0.6696 0.6197 0.079 Uiso 1 1 calc R . . H91B H 0.1090 0.5723 0.6331 0.079 Uiso 1 1 calc R . . C92 C 0.259(3) 0.6399(15) 0.5906(7) 0.060(6) Uani 1 1 d U . . H92A H 0.2815 0.5787 0.5797 0.072 Uiso 1 1 calc R . . H92B H 0.2285 0.6779 0.5679 0.072 Uiso 1 1 calc R . . O5 O 0.3823(18) 0.6767(11) 0.6046(5) 0.066(4) Uani 1 1 d U . . C93 C 0.035(8) 0.444(4) 0.4735(18) 0.11(2) Uani 0.50 1 d PDU A -1 H93A H 0.0279 0.4057 0.4491 0.133 Uiso 0.50 1 calc PR A -1 H93B H 0.1396 0.4484 0.4772 0.133 Uiso 0.50 1 calc PR A -1 C94 C -0.023(9) 0.535(4) 0.466(2) 0.09(2) Uani 0.50 1 d PDU A -1 H94A H -0.1301 0.5392 0.4663 0.113 Uiso 0.50 1 calc PR A -1 H94B H 0.0308 0.5682 0.4417 0.113 Uiso 0.50 1 calc PR A -1 C95 C 0.049(9) 0.554(5) 0.520(3) 0.13(3) Uani 0.50 1 d PDU A -1 H95A H 0.1543 0.5394 0.5197 0.151 Uiso 0.50 1 calc PR A -1 H95B H 0.0229 0.6128 0.5324 0.151 Uiso 0.50 1 calc PR A -1 C96 C -0.052(8) 0.480(3) 0.5341(16) 0.082(18) Uani 0.50 1 d PDU A -1 H96A H -0.0334 0.4608 0.5624 0.099 Uiso 0.50 1 calc PR A -1 H96B H -0.1534 0.5030 0.5364 0.099 Uiso 0.50 1 calc PR A -1 O6 O -0.042(4) 0.403(2) 0.5090(12) 0.081(10) Uani 0.50 1 d PDU A -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 C1 0.009(7) 0.025(6) 0.028(7) -0.007(5) -0.002(6) 0.001(5) C2 0.013(7) 0.017(6) 0.027(6) -0.004(5) -0.004(6) 0.004(5) C3 0.009(6) 0.008(5) 0.024(6) -0.002(5) 0.000(5) -0.005(4) C4 0.014(7) 0.012(5) 0.032(7) -0.007(5) -0.011(6) -0.003(4) C5 0.014(7) 0.020(6) 0.025(6) -0.007(5) -0.004(6) 0.004(5) C6 0.006(6) 0.018(6) 0.027(6) -0.002(5) -0.007(5) -0.003(4) C7 0.009(6) 0.016(6) 0.022(6) -0.004(5) -0.006(5) 0.003(4) C8 0.014(7) 0.011(5) 0.030(7) 0.001(5) -0.004(6) 0.004(5) C9 0.020(7) 0.023(6) 0.029(7) -0.011(5) -0.008(6) 0.008(5) C10 0.007(6) 0.016(5) 0.024(6) -0.005(5) -0.003(5) -0.003(4) C11 0.011(7) 0.017(6) 0.029(7) -0.001(5) -0.002(6) 0.003(5) C12 0.012(7) 0.011(5) 0.026(6) -0.006(5) -0.007(5) -0.001(4) C13 0.018(7) 0.022(6) 0.025(6) -0.010(5) -0.003(6) -0.003(5) C14 0.012(6) 0.011(5) 0.023(6) -0.005(5) -0.003(5) 0.001(4) C15 0.016(7) 0.019(6) 0.028(6) -0.008(5) -0.006(6) 0.004(5) C16 0.017(7) 0.008(5) 0.023(6) -0.002(5) -0.008(5) 0.004(4) C17 0.019(7) 0.011(5) 0.026(6) -0.005(5) -0.007(6) 0.002(5) C18 0.016(7) 0.012(5) 0.031(7) -0.003(5) -0.007(6) -0.001(5) C19 0.020(9) 0.021(7) 0.043(9) -0.011(6) -0.004(7) 0.005(6) N1 0.010(4) 0.018(4) 0.022(4) -0.002(3) -0.004(3) 0.002(3) O1 0.010(5) 0.015(4) 0.038(5) -0.015(4) -0.007(4) 0.002(3) C20 0.039(8) 0.032(7) 0.045(8) -0.001(6) -0.007(7) -0.005(6) C21 0.039(8) 0.033(7) 0.035(7) 0.000(6) -0.004(7) 0.003(6) C22 0.031(8) 0.028(6) 0.031(7) -0.005(6) -0.009(6) 0.000(5) C23 0.022(7) 0.038(7) 0.042(7) -0.007(6) -0.014(6) -0.004(6) C24 0.039(8) 0.036(7) 0.036(7) -0.008(6) -0.010(7) 0.006(6) C25 0.035(8) 0.028(7) 0.036(7) 0.000(6) -0.009(6) 0.001(6) C26 0.036(8) 0.036(7) 0.042(8) -0.006(6) -0.008(7) -0.010(6) C27 0.033(8) 0.026(6) 0.031(7) -0.009(6) -0.012(6) -0.008(5) C28 0.049(9) 0.046(8) 0.043(8) -0.017(7) -0.005(7) -0.013(7) C29 0.053(9) 0.059(8) 0.051(8) -0.018(7) -0.003(7) -0.013(7) C30 0.035(8) 0.031(7) 0.038(7) -0.013(6) -0.010(6) -0.006(6) C31 0.048(9) 0.048(8) 0.043(8) -0.008(7) -0.006(7) -0.015(7) C32 0.045(8) 0.038(7) 0.039(8) -0.005(6) -0.002(7) 0.003(6) C33 0.034(8) 0.035(7) 0.039(7) -0.005(6) -0.009(7) 0.003(6) C34 0.033(8) 0.033(7) 0.038(7) -0.012(6) -0.004(6) -0.003(6) C35 0.028(8) 0.033(7) 0.041(7) -0.009(6) -0.005(6) -0.012(6) C36 0.033(8) 0.037(7) 0.034(7) -0.010(6) -0.013(6) -0.004(6) C37 0.034(8) 0.041(7) 0.039(7) -0.008(6) -0.009(7) -0.010(6) C38 0.023(9) 0.021(7) 0.037(8) -0.009(6) -0.002(7) -0.004(6) N2 0.033(7) 0.032(6) 0.037(7) -0.002(5) -0.010(6) -0.004(5) O2 0.042(7) 0.055(6) 0.047(6) -0.023(5) -0.011(6) -0.001(5) C39 0.039(8) 0.025(6) 0.045(8) -0.006(6) -0.006(7) -0.001(6) C40 0.028(8) 0.030(7) 0.040(7) -0.005(6) -0.017(6) -0.009(5) C41 0.022(7) 0.023(6) 0.028(7) 0.000(5) -0.004(6) -0.001(5) C42 0.025(7) 0.026(6) 0.034(7) 0.001(6) -0.004(6) -0.003(5) C43 0.029(8) 0.037(7) 0.040(7) -0.002(6) -0.007(6) -0.009(6) C44 0.033(8) 0.034(7) 0.031(7) -0.005(6) -0.008(6) -0.002(6) C45 0.023(8) 0.037(7) 0.035(7) -0.007(6) -0.006(6) -0.010(6) C46 0.025(7) 0.008(5) 0.041(7) -0.009(5) -0.010(6) -0.008(5) C47 0.027(8) 0.028(6) 0.035(7) -0.004(6) -0.011(6) -0.001(5) C48 0.033(8) 0.040(7) 0.041(8) -0.007(6) -0.001(7) -0.003(6) C49 0.029(8) 0.028(6) 0.035(7) -0.003(6) -0.005(6) -0.008(5) C50 0.028(8) 0.038(7) 0.032(7) -0.008(6) -0.014(6) 0.006(6) C51 0.033(8) 0.037(7) 0.035(7) -0.006(6) -0.007(7) -0.005(6) C52 0.022(7) 0.030(6) 0.031(7) -0.003(6) -0.014(6) -0.006(5) C53 0.016(7) 0.026(6) 0.031(7) -0.003(5) -0.007(6) -0.002(5) C54 0.019(7) 0.029(6) 0.029(7) -0.004(5) -0.012(6) -0.004(5) C55 0.017(7) 0.028(6) 0.031(7) -0.007(5) -0.008(6) -0.003(5) C56 0.021(7) 0.040(7) 0.026(7) -0.005(6) -0.002(6) -0.003(5) C57 0.035(10) 0.042(9) 0.037(9) -0.008(7) -0.010(8) 0.007(7) N3 0.029(7) 0.032(6) 0.035(6) -0.005(5) 0.000(6) -0.008(5) O3 0.034(6) 0.033(5) 0.037(6) -0.010(4) -0.017(5) -0.004(4) C58 0.011(7) 0.019(6) 0.030(7) -0.001(5) 0.002(6) 0.001(5) C59 0.012(7) 0.017(6) 0.026(6) -0.003(5) -0.009(6) -0.004(5) C60 0.011(7) 0.014(5) 0.020(6) -0.003(5) 0.001(5) -0.006(4) C61 0.014(7) 0.014(6) 0.032(7) -0.007(5) -0.007(6) -0.001(5) C62 0.010(7) 0.020(6) 0.030(7) -0.009(5) -0.003(6) 0.004(5) C63 0.014(7) 0.019(6) 0.025(6) -0.001(5) -0.008(5) 0.002(5) C64 0.009(6) 0.010(5) 0.027(6) 0.001(5) -0.010(5) 0.002(4) C65 0.012(7) 0.015(5) 0.025(6) 0.001(5) -0.001(5) 0.004(5) C66 0.012(7) 0.010(5) 0.029(6) 0.002(5) -0.005(6) -0.010(4) C67 0.009(7) 0.025(6) 0.026(6) -0.009(5) -0.011(5) 0.001(5) C68 0.012(7) 0.013(5) 0.028(6) -0.002(5) -0.007(6) -0.003(4) C69 0.015(7) 0.016(6) 0.025(6) -0.009(5) -0.005(6) 0.000(5) C70 0.015(7) 0.017(6) 0.032(7) -0.009(5) -0.005(6) -0.007(5) C71 0.015(7) 0.009(5) 0.024(6) -0.001(5) -0.008(5) -0.002(4) C72 0.022(7) 0.020(6) 0.024(6) -0.002(5) -0.007(6) 0.008(5) C73 0.011(6) 0.007(5) 0.025(6) -0.001(5) -0.007(5) -0.001(4) C74 0.022(7) 0.013(6) 0.027(6) -0.006(5) -0.002(6) 0.004(5) C75 0.023(7) 0.010(5) 0.034(7) -0.003(5) -0.007(6) -0.002(5) C76 0.026(9) 0.016(7) 0.042(9) -0.010(6) -0.008(7) 0.007(6) N4 0.013(6) 0.025(5) 0.034(6) -0.007(5) -0.003(5) 0.005(4) O4 0.015(5) 0.010(4) 0.034(5) -0.010(4) -0.009(4) 0.003(3) C77 0.010(7) 0.022(6) 0.023(6) -0.001(5) -0.009(6) 0.000(5) C78 0.012(7) 0.017(6) 0.021(6) -0.002(5) -0.010(5) -0.002(5) C79 0.019(7) 0.013(5) 0.023(6) -0.004(5) -0.005(6) -0.006(5) C80 0.026(7) 0.018(6) 0.021(6) -0.006(5) 0.000(6) 0.000(5) C81 0.015(7) 0.024(6) 0.027(7) 0.008(5) 0.000(6) 0.009(5) C82 0.015(7) 0.019(6) 0.023(6) 0.003(5) -0.002(6) 0.001(5) F1 0.018(5) 0.027(4) 0.046(5) -0.016(4) -0.019(4) 0.009(3) F2 0.028(6) 0.029(5) 0.045(5) -0.018(4) -0.008(4) 0.007(4) F3 0.016(5) 0.033(5) 0.046(5) -0.005(4) -0.012(4) 0.015(4) F4 0.011(5) 0.032(5) 0.039(5) -0.010(4) -0.016(4) 0.002(3) I1 0.0146(6) 0.0147(4) 0.0319(5) -0.0078(4) -0.0066(4) -0.0007(3) I2 0.0240(6) 0.0219(5) 0.0360(6) -0.0119(4) -0.0117(5) -0.0028(4) C83 0.026(7) 0.022(6) 0.016(6) -0.008(5) -0.015(6) -0.003(5) C84 0.012(7) 0.020(6) 0.024(6) -0.002(5) -0.001(6) 0.001(5) C85 0.009(6) 0.021(6) 0.010(6) -0.003(5) -0.007(5) -0.006(4) C86 0.016(7) 0.019(6) 0.026(7) 0.001(5) -0.007(6) -0.006(5) C87 0.013(5) 0.008(4) 0.021(4) 0.002(3) -0.007(4) -0.003(3) C88 0.027(7) 0.018(6) 0.023(6) -0.002(5) -0.006(6) 0.002(5) F5 0.023(5) 0.026(4) 0.032(5) -0.009(4) -0.012(4) 0.004(3) F6 0.015(5) 0.028(4) 0.036(5) -0.013(4) -0.017(4) -0.003(3) F7 0.020(5) 0.023(4) 0.045(5) -0.005(4) -0.010(4) 0.010(3) F8 0.024(5) 0.024(4) 0.049(6) -0.012(4) -0.004(4) 0.005(3) I3 0.0217(6) 0.0215(5) 0.0345(6) -0.0088(4) -0.0105(5) -0.0036(4) I4 0.0141(6) 0.0150(4) 0.0339(6) -0.0086(4) -0.0038(4) 0.0001(3) C89 0.059(9) 0.046(8) 0.064(9) -0.014(7) 0.004(8) -0.009(7) C90 0.077(11) 0.066(10) 0.074(10) -0.008(8) 0.012(8) -0.007(8) C91 0.064(10) 0.065(9) 0.068(10) 0.016(8) -0.005(8) 0.010(8) C92 0.058(10) 0.059(9) 0.060(9) -0.004(7) -0.001(8) 0.004(7) O5 0.056(8) 0.075(8) 0.060(7) -0.012(6) 0.010(6) 0.008(6) C93 0.11(3) 0.11(3) 0.11(3) -0.002(10) -0.014(10) 0.001(10) C94 0.09(2) 0.10(2) 0.09(2) 0.003(10) -0.006(10) 0.004(10) C95 0.12(3) 0.13(3) 0.13(3) -0.002(10) -0.014(10) -0.002(10) C96 0.08(2) 0.083(19) 0.082(19) 0.005(10) -0.012(10) -0.004(10) O6 0.083(13) 0.083(13) 0.079(13) -0.001(9) -0.014(9) -0.002(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 C1 N1 1.318(19) . ? C1 C2 1.395(18) . ? C1 H1 0.9500 . ? C2 C3 1.39(2) . ? C2 H2 0.9500 . ? C3 C4 1.376(19) . ? C3 C6 1.442(18) . ? C4 C5 1.416(18) . ? C4 H4 0.9500 . ? C5 N1 1.319(19) . ? C5 H5 0.9500 . ? C6 C7 1.339(19) . ? C6 H6 0.9500 . ? C7 C8 1.478(17) . ? C7 H7 0.9500 . ? C8 C13 1.37(2) . ? C8 C9 1.40(2) . ? C9 C10 1.395(18) . ? C9 H9 0.9500 . ? C10 C11 1.38(2) . ? C10 H10 0.9500 . ? C11 C12 1.38(2) . ? C11 O1 1.379(16) . ? C12 C13 1.409(19) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O1 1.442(16) . ? C14 C15 1.528(17) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.519(18) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.532(17) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.518(18) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.532(18) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N2 1.32(2) . ? C20 C21 1.42(3) . ? C20 H20 0.9500 . ? C21 C22 1.34(3) . ? C21 H21 0.9500 . ? C22 C23 1.39(2) . ? C22 C25 1.45(2) . ? C23 C24 1.36(3) . ? C23 H23 0.9500 . ? C24 N2 1.35(2) . ? C24 H24 0.9500 . ? C25 C26 1.34(2) . ? C25 H25 0.9500 . ? C26 C27 1.43(2) . ? C26 H26 0.9500 . ? C27 C28 1.38(3) . ? C27 C32 1.39(2) . ? C28 C29 1.35(3) . ? C28 H28 0.9500 . ? C29 C30 1.37(3) . ? C29 H29 0.9500 . ? C30 O2 1.37(2) . ? C30 C31 1.37(3) . ? C31 C32 1.46(3) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 O2 1.42(2) . ? C33 C34 1.49(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.52(2) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.51(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.49(2) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.50(2) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 N3 1.34(2) . ? C39 C40 1.37(2) . ? C39 H39 0.9500 . ? C40 C41 1.39(2) . ? C40 H40 0.9500 . ? C41 C42 1.42(2) . ? C41 C44 1.44(2) . ? C42 C43 1.35(2) . ? C42 H42 0.9500 . ? C43 N3 1.33(2) . ? C43 H43 0.9500 . ? C44 C45 1.31(2) . ? C44 H44 0.9500 . ? C45 C46 1.45(2) . ? C45 H45 0.9500 . ? C46 C51 1.34(2) . ? C46 C47 1.42(2) . ? C47 C48 1.34(2) . ? C47 H47 0.9500 . ? C48 C49 1.40(3) . ? C48 H48 0.9500 . ? C49 O3 1.355(19) . ? C49 C50 1.40(2) . ? C50 C51 1.38(2) . ? C50 H50 0.9500 . ? C51 H51 0.9500 . ? C52 O3 1.45(2) . ? C52 C53 1.51(2) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.52(2) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.52(2) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 C56 1.53(2) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 C57 1.50(2) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? C58 N4 1.32(2) . ? C58 C59 1.381(19) . ? C58 H58 0.9500 . ? C59 C60 1.40(2) . ? C59 H59 0.9500 . ? C60 C61 1.398(19) . ? C60 C63 1.461(18) . ? C61 C62 1.403(18) . ? C61 H61 0.9500 . ? C62 N4 1.32(2) . ? C62 H62 0.9500 . ? C63 C64 1.34(2) . ? C63 H63 0.9500 . ? C64 C65 1.491(17) . ? C64 H64 0.9500 . ? C65 C66 1.37(2) . ? C65 C70 1.38(2) . ? C66 C67 1.378(19) . ? C66 H66 0.9500 . ? C67 C68 1.40(2) . ? C67 H67 0.9500 . ? C68 O4 1.365(16) . ? C68 C69 1.37(2) . ? C69 C70 1.408(19) . ? C69 H69 0.9500 . ? C70 H70 0.9500 . ? C71 O4 1.435(15) . ? C71 C72 1.514(17) . ? C71 H71A 0.9900 . ? C71 H71B 0.9900 . ? C72 C73 1.524(18) . ? C72 H72A 0.9900 . ? C72 H72B 0.9900 . ? C73 C74 1.541(17) . ? C73 H73A 0.9900 . ? C73 H73B 0.9900 . ? C74 C75 1.502(19) . ? C74 H74A 0.9900 . ? C74 H74B 0.9900 . ? C75 C76 1.526(19) . ? C75 H75A 0.9900 . ? C75 H75B 0.9900 . ? C76 H76A 0.9800 . ? C76 H76B 0.9800 . ? C76 H76C 0.9800 . ? C77 C78 1.36(2) . ? C77 C82 1.390(19) . ? C77 I1 2.098(13) . ? C78 F1 1.351(16) . ? C78 C79 1.405(18) . ? C79 C80 1.40(2) . ? C79 I2 2.054(15) . ? C80 F2 1.342(15) . ? C80 C81 1.37(2) . ? C81 F3 1.298(16) . ? C81 C82 1.41(2) . ? C82 F4 1.331(18) . ? C83 C84 1.392(19) . ? C83 C88 1.41(2) . ? C83 I3 2.085(15) . ? C84 F5 1.331(16) . ? C84 C85 1.35(2) . ? C85 C86 1.41(2) . ? C85 I4 2.094(13) . ? C86 F6 1.317(18) . ? C86 C87 1.376(18) . ? C87 F7 1.329(16) . ? C87 C88 1.35(2) . ? C88 F8 1.353(15) . ? C89 O5 1.40(2) . ? C89 C90 1.47(3) . ? C89 H89A 0.9900 . ? C89 H89B 0.9900 . ? C90 C91 1.47(4) . ? C90 H90A 0.9900 . ? C90 H90B 0.9900 . ? C91 C92 1.50(3) . ? C91 H91A 0.9900 . ? C91 H91B 0.9900 . ? C92 O5 1.40(3) . ? C92 H92A 0.9900 . ? C92 H92B 0.9900 . ? C93 O6 1.400(5) . ? C93 C94 1.480(5) . ? C93 H93A 0.9900 . ? C93 H93B 0.9900 . ? C94 C95 1.97(10) . ? C94 H94A 0.9900 . ? C94 H94B 0.9900 . ? C95 C96 1.480(5) . ? C95 H95A 0.9900 . ? C95 H95B 0.9900 . ? C96 O6 1.400(5) . ? C96 H96A 0.9900 . ? C96 H96B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.5(16) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C3 C2 C1 120.3(14) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 115.7(12) . . ? C4 C3 C6 119.4(14) . . ? C2 C3 C6 124.9(13) . . ? C3 C4 C5 120.3(15) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 123.0(14) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C7 C6 C3 125.8(15) . . ? C7 C6 H6 117.1 . . ? C3 C6 H6 117.1 . . ? C6 C7 C8 125.8(15) . . ? C6 C7 H7 117.1 . . ? C8 C7 H7 117.1 . . ? C13 C8 C9 117.9(13) . . ? C13 C8 C7 119.6(15) . . ? C9 C8 C7 122.5(13) . . ? C10 C9 C8 119.9(14) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 121.3(15) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 119.5(12) . . ? C12 C11 O1 125.8(13) . . ? C10 C11 O1 114.7(14) . . ? C11 C12 C13 119.3(13) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C8 C13 C12 122.1(16) . . ? C8 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? O1 C14 C15 106.0(11) . . ? O1 C14 H14A 110.5 . . ? C15 C14 H14A 110.5 . . ? O1 C14 H14B 110.5 . . ? C15 C14 H14B 110.5 . . ? H14A C14 H14B 108.7 . . ? C16 C15 C14 110.8(12) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 113.1(12) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 113.0(12) . . ? C18 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? C18 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C17 C18 C19 112.7(13) . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 N1 C5 117.2(12) . . ? C11 O1 C14 116.3(12) . . ? N2 C20 C21 122.8(17) . . ? N2 C20 H20 118.6 . . ? C21 C20 H20 118.6 . . ? C22 C21 C20 119.9(16) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 116.2(16) . . ? C21 C22 C25 125.2(15) . . ? C23 C22 C25 118.6(16) . . ? C24 C23 C22 122.1(17) . . ? C24 C23 H23 118.9 . . ? C22 C23 H23 118.9 . . ? N2 C24 C23 121.8(16) . . ? N2 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? C26 C25 C22 125.9(17) . . ? C26 C25 H25 117.0 . . ? C22 C25 H25 117.0 . . ? C25 C26 C27 126.6(17) . . ? C25 C26 H26 116.7 . . ? C27 C26 H26 116.7 . . ? C28 C27 C32 118.2(17) . . ? C28 C27 C26 123.3(16) . . ? C32 C27 C26 118.2(16) . . ? C29 C28 C27 123.2(18) . . ? C29 C28 H28 118.4 . . ? C27 C28 H28 118.4 . . ? C28 C29 C30 120(2) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? O2 C30 C31 125.0(16) . . ? O2 C30 C29 115.6(17) . . ? C31 C30 C29 119.4(18) . . ? C30 C31 C32 120.3(17) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? C27 C32 C31 117.9(17) . . ? C27 C32 H32 121.1 . . ? C31 C32 H32 121.1 . . ? O2 C33 C34 107.5(14) . . ? O2 C33 H33A 110.2 . . ? C34 C33 H33A 110.2 . . ? O2 C33 H33B 110.2 . . ? C34 C33 H33B 110.2 . . ? H33A C33 H33B 108.5 . . ? C33 C34 C35 112.5(14) . . ? C33 C34 H34A 109.1 . . ? C35 C34 H34A 109.1 . . ? C33 C34 H34B 109.1 . . ? C35 C34 H34B 109.1 . . ? H34A C34 H34B 107.8 . . ? C36 C35 C34 112.5(14) . . ? C36 C35 H35A 109.1 . . ? C34 C35 H35A 109.1 . . ? C36 C35 H35B 109.1 . . ? C34 C35 H35B 109.1 . . ? H35A C35 H35B 107.8 . . ? C37 C36 C35 115.1(15) . . ? C37 C36 H36A 108.5 . . ? C35 C36 H36A 108.5 . . ? C37 C36 H36B 108.5 . . ? C35 C36 H36B 108.5 . . ? H36A C36 H36B 107.5 . . ? C36 C37 C38 114.8(15) . . ? C36 C37 H37A 108.6 . . ? C38 C37 H37A 108.6 . . ? C36 C37 H37B 108.6 . . ? C38 C37 H37B 108.6 . . ? H37A C37 H37B 107.5 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C20 N2 C24 117.2(16) . . ? C30 O2 C33 120.1(14) . . ? N3 C39 C40 122.8(15) . . ? N3 C39 H39 118.6 . . ? C40 C39 H39 118.6 . . ? C39 C40 C41 120.9(17) . . ? C39 C40 H40 119.5 . . ? C41 C40 H40 119.5 . . ? C40 C41 C42 114.6(15) . . ? C40 C41 C44 124.5(16) . . ? C42 C41 C44 120.9(14) . . ? C43 C42 C41 120.7(15) . . ? C43 C42 H42 119.7 . . ? C41 C42 H42 119.7 . . ? N3 C43 C42 123.7(18) . . ? N3 C43 H43 118.1 . . ? C42 C43 H43 118.1 . . ? C45 C44 C41 127.4(16) . . ? C45 C44 H44 116.3 . . ? C41 C44 H44 116.3 . . ? C44 C45 C46 127.6(16) . . ? C44 C45 H45 116.2 . . ? C46 C45 H45 116.2 . . ? C51 C46 C47 116.5(15) . . ? C51 C46 C45 121.0(14) . . ? C47 C46 C45 122.5(16) . . ? C48 C47 C46 121.6(17) . . ? C48 C47 H47 119.2 . . ? C46 C47 H47 119.2 . . ? C47 C48 C49 120.5(16) . . ? C47 C48 H48 119.8 . . ? C49 C48 H48 119.8 . . ? O3 C49 C50 125.9(17) . . ? O3 C49 C48 115.1(14) . . ? C50 C49 C48 119.1(16) . . ? C51 C50 C49 118.0(17) . . ? C51 C50 H50 121.0 . . ? C49 C50 H50 121.0 . . ? C46 C51 C50 124.2(16) . . ? C46 C51 H51 117.9 . . ? C50 C51 H51 117.9 . . ? O3 C52 C53 104.8(12) . . ? O3 C52 H52A 110.8 . . ? C53 C52 H52A 110.8 . . ? O3 C52 H52B 110.8 . . ? C53 C52 H52B 110.8 . . ? H52A C52 H52B 108.9 . . ? C52 C53 C54 111.2(12) . . ? C52 C53 H53A 109.4 . . ? C54 C53 H53A 109.4 . . ? C52 C53 H53B 109.4 . . ? C54 C53 H53B 109.4 . . ? H53A C53 H53B 108.0 . . ? C55 C54 C53 112.6(13) . . ? C55 C54 H54A 109.1 . . ? C53 C54 H54A 109.1 . . ? C55 C54 H54B 109.1 . . ? C53 C54 H54B 109.1 . . ? H54A C54 H54B 107.8 . . ? C54 C55 C56 114.1(13) . . ? C54 C55 H55A 108.7 . . ? C56 C55 H55A 108.7 . . ? C54 C55 H55B 108.7 . . ? C56 C55 H55B 108.7 . . ? H55A C55 H55B 107.6 . . ? C57 C56 C55 113.8(14) . . ? C57 C56 H56A 108.8 . . ? C55 C56 H56A 108.8 . . ? C57 C56 H56B 108.8 . . ? C55 C56 H56B 108.8 . . ? H56A C56 H56B 107.7 . . ? C56 C57 H57A 109.5 . . ? C56 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C56 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C43 N3 C39 117.1(15) . . ? C49 O3 C52 115.8(12) . . ? N4 C58 C59 125.8(16) . . ? N4 C58 H58 117.1 . . ? C59 C58 H58 117.1 . . ? C58 C59 C60 118.7(14) . . ? C58 C59 H59 120.6 . . ? C60 C59 H59 120.6 . . ? C59 C60 C61 116.7(12) . . ? C59 C60 C63 124.2(13) . . ? C61 C60 C63 119.0(14) . . ? C60 C61 C62 118.0(15) . . ? C60 C61 H61 121.0 . . ? C62 C61 H61 121.0 . . ? N4 C62 C61 125.4(14) . . ? N4 C62 H62 117.3 . . ? C61 C62 H62 117.3 . . ? C64 C63 C60 125.3(15) . . ? C64 C63 H63 117.4 . . ? C60 C63 H63 117.4 . . ? C63 C64 C65 124.6(14) . . ? C63 C64 H64 117.7 . . ? C65 C64 H64 117.7 . . ? C66 C65 C70 117.5(13) . . ? C66 C65 C64 124.4(13) . . ? C70 C65 C64 118.1(14) . . ? C65 C66 C67 123.1(14) . . ? C65 C66 H66 118.5 . . ? C67 C66 H66 118.5 . . ? C66 C67 C68 118.8(15) . . ? C66 C67 H67 120.6 . . ? C68 C67 H67 120.6 . . ? O4 C68 C69 126.9(13) . . ? O4 C68 C67 113.3(14) . . ? C69 C68 C67 119.8(12) . . ? C68 C69 C70 119.6(13) . . ? C68 C69 H69 120.2 . . ? C70 C69 H69 120.2 . . ? C65 C70 C69 121.2(15) . . ? C65 C70 H70 119.4 . . ? C69 C70 H70 119.4 . . ? O4 C71 C72 107.4(12) . . ? O4 C71 H71A 110.2 . . ? C72 C71 H71A 110.2 . . ? O4 C71 H71B 110.2 . . ? C72 C71 H71B 110.2 . . ? H71A C71 H71B 108.5 . . ? C71 C72 C73 111.8(12) . . ? C71 C72 H72A 109.3 . . ? C73 C72 H72A 109.3 . . ? C71 C72 H72B 109.3 . . ? C73 C72 H72B 109.3 . . ? H72A C72 H72B 107.9 . . ? C72 C73 C74 112.1(12) . . ? C72 C73 H73A 109.2 . . ? C74 C73 H73A 109.2 . . ? C72 C73 H73B 109.2 . . ? C74 C73 H73B 109.2 . . ? H73A C73 H73B 107.9 . . ? C75 C74 C73 112.4(13) . . ? C75 C74 H74A 109.1 . . ? C73 C74 H74A 109.1 . . ? C75 C74 H74B 109.1 . . ? C73 C74 H74B 109.1 . . ? H74A C74 H74B 107.9 . . ? C74 C75 C76 112.9(13) . . ? C74 C75 H75A 109.0 . . ? C76 C75 H75A 109.0 . . ? C74 C75 H75B 109.0 . . ? C76 C75 H75B 109.0 . . ? H75A C75 H75B 107.8 . . ? C75 C76 H76A 109.5 . . ? C75 C76 H76B 109.5 . . ? H76A C76 H76B 109.5 . . ? C75 C76 H76C 109.5 . . ? H76A C76 H76C 109.5 . . ? H76B C76 H76C 109.5 . . ? C58 N4 C62 115.0(12) . . ? C68 O4 C71 117.3(12) . . ? C78 C77 C82 116.1(13) . . ? C78 C77 I1 120.8(10) . . ? C82 C77 I1 123.0(11) . . ? F1 C78 C77 118.1(12) . . ? F1 C78 C79 116.1(13) . . ? C77 C78 C79 125.8(13) . . ? C80 C79 C78 114.4(13) . . ? C80 C79 I2 122.8(10) . . ? C78 C79 I2 122.8(11) . . ? F2 C80 C81 116.1(13) . . ? F2 C80 C79 119.6(14) . . ? C81 C80 C79 124.3(13) . . ? F3 C81 C80 122.6(13) . . ? F3 C81 C82 120.8(15) . . ? C80 C81 C82 116.6(13) . . ? F4 C82 C77 119.6(12) . . ? F4 C82 C81 117.6(13) . . ? C77 C82 C81 122.8(15) . . ? C84 C83 C88 116.4(13) . . ? C84 C83 I3 123.9(12) . . ? C88 C83 I3 119.5(10) . . ? F5 C84 C85 118.3(12) . . ? F5 C84 C83 117.5(13) . . ? C85 C84 C83 124.0(14) . . ? C84 C85 C86 116.8(12) . . ? C84 C85 I4 122.3(10) . . ? C86 C85 I4 120.7(10) . . ? F6 C86 C87 118.9(13) . . ? F6 C86 C85 120.1(12) . . ? C87 C86 C85 121.0(13) . . ? F7 C87 C88 119.0(12) . . ? F7 C87 C86 120.1(13) . . ? C88 C87 C86 120.3(13) . . ? C87 C88 F8 118.8(14) . . ? C87 C88 C83 121.1(12) . . ? F8 C88 C83 120.2(13) . . ? O5 C89 C90 106.5(18) . . ? O5 C89 H89A 110.4 . . ? C90 C89 H89A 110.4 . . ? O5 C89 H89B 110.4 . . ? C90 C89 H89B 110.4 . . ? H89A C89 H89B 108.6 . . ? C91 C90 C89 106(2) . . ? C91 C90 H90A 110.6 . . ? C89 C90 H90A 110.6 . . ? C91 C90 H90B 110.6 . . ? C89 C90 H90B 110.6 . . ? H90A C90 H90B 108.8 . . ? C90 C91 C92 104(2) . . ? C90 C91 H91A 111.0 . . ? C92 C91 H91A 111.0 . . ? C90 C91 H91B 111.0 . . ? C92 C91 H91B 111.0 . . ? H91A C91 H91B 109.0 . . ? O5 C92 C91 109(2) . . ? O5 C92 H92A 109.9 . . ? C91 C92 H92A 109.9 . . ? O5 C92 H92B 109.9 . . ? C91 C92 H92B 109.9 . . ? H92A C92 H92B 108.3 . . ? C92 O5 C89 106.7(17) . . ? O6 C93 C94 112(5) . . ? O6 C93 H93A 109.2 . . ? C94 C93 H93A 109.2 . . ? O6 C93 H93B 109.2 . . ? C94 C93 H93B 109.2 . . ? H93A C93 H93B 107.9 . . ? C93 C94 C95 80(5) . . ? C93 C94 H94A 115.3 . . ? C95 C94 H94A 115.3 . . ? C93 C94 H94B 115.3 . . ? C95 C94 H94B 115.3 . . ? H94A C94 H94B 112.4 . . ? C96 C95 C94 84(4) . . ? C96 C95 H95A 114.7 . . ? C94 C95 H95A 114.7 . . ? C96 C95 H95B 114.7 . . ? C94 C95 H95B 114.7 . . ? H95A C95 H95B 111.7 . . ? O6 C96 C95 116(5) . . ? O6 C96 H96A 108.4 . . ? C95 C96 H96A 108.4 . . ? O6 C96 H96B 108.4 . . ? C95 C96 H96B 108.4 . . ? H96A C96 H96B 107.4 . . ? C93 O6 C96 97(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -2(2) . . . . ? C1 C2 C3 C4 2.5(19) . . . . ? C1 C2 C3 C6 179.2(13) . . . . ? C2 C3 C4 C5 -2(2) . . . . ? C6 C3 C4 C5 -178.4(13) . . . . ? C3 C4 C5 N1 0(2) . . . . ? C4 C3 C6 C7 -173.8(14) . . . . ? C2 C3 C6 C7 10(2) . . . . ? C3 C6 C7 C8 -179.3(13) . . . . ? C6 C7 C8 C13 173.2(14) . . . . ? C6 C7 C8 C9 -6(2) . . . . ? C13 C8 C9 C10 -2(2) . . . . ? C7 C8 C9 C10 177.8(13) . . . . ? C8 C9 C10 C11 1(2) . . . . ? C9 C10 C11 C12 0(2) . . . . ? C9 C10 C11 O1 -177.7(13) . . . . ? C10 C11 C12 C13 -1(2) . . . . ? O1 C11 C12 C13 176.7(13) . . . . ? C9 C8 C13 C12 1(2) . . . . ? C7 C8 C13 C12 -178.6(13) . . . . ? C11 C12 C13 C8 0(2) . . . . ? O1 C14 C15 C16 -178.2(11) . . . . ? C14 C15 C16 C17 -179.5(12) . . . . ? C15 C16 C17 C18 -179.3(12) . . . . ? C16 C17 C18 C19 -178.7(12) . . . . ? C2 C1 N1 C5 1(2) . . . . ? C4 C5 N1 C1 0(2) . . . . ? C12 C11 O1 C14 2(2) . . . . ? C10 C11 O1 C14 -179.8(11) . . . . ? C15 C14 O1 C11 -178.8(11) . . . . ? N2 C20 C21 C22 -1(3) . . . . ? C20 C21 C22 C23 1(2) . . . . ? C20 C21 C22 C25 -179.0(15) . . . . ? C21 C22 C23 C24 0(2) . . . . ? C25 C22 C23 C24 179.7(16) . . . . ? C22 C23 C24 N2 0(3) . . . . ? C21 C22 C25 C26 -10(3) . . . . ? C23 C22 C25 C26 170.4(17) . . . . ? C22 C25 C26 C27 179.7(16) . . . . ? C25 C26 C27 C28 -7(3) . . . . ? C25 C26 C27 C32 166.3(17) . . . . ? C32 C27 C28 C29 6(3) . . . . ? C26 C27 C28 C29 180(2) . . . . ? C27 C28 C29 C30 -3(3) . . . . ? C28 C29 C30 O2 -180.0(19) . . . . ? C28 C29 C30 C31 2(3) . . . . ? O2 C30 C31 C32 177.6(17) . . . . ? C29 C30 C31 C32 -4(3) . . . . ? C28 C27 C32 C31 -8(3) . . . . ? C26 C27 C32 C31 177.7(17) . . . . ? C30 C31 C32 C27 8(3) . . . . ? O2 C33 C34 C35 173.3(14) . . . . ? C33 C34 C35 C36 178.1(15) . . . . ? C34 C35 C36 C37 -175.0(15) . . . . ? C35 C36 C37 C38 178.6(16) . . . . ? C21 C20 N2 C24 1(2) . . . . ? C23 C24 N2 C20 0(2) . . . . ? C31 C30 O2 C33 7(3) . . . . ? C29 C30 O2 C33 -171.4(16) . . . . ? C34 C33 O2 C30 166.3(15) . . . . ? N3 C39 C40 C41 3(3) . . . . ? C39 C40 C41 C42 -2(2) . . . . ? C39 C40 C41 C44 179.5(16) . . . . ? C40 C41 C42 C43 0(2) . . . . ? C44 C41 C42 C43 178.0(15) . . . . ? C41 C42 C43 N3 3(3) . . . . ? C40 C41 C44 C45 -1(3) . . . . ? C42 C41 C44 C45 -179.1(16) . . . . ? C41 C44 C45 C46 -178.1(16) . . . . ? C44 C45 C46 C51 -178.5(17) . . . . ? C44 C45 C46 C47 1(3) . . . . ? C51 C46 C47 C48 -4(2) . . . . ? C45 C46 C47 C48 176.9(16) . . . . ? C46 C47 C48 C49 3(3) . . . . ? C47 C48 C49 O3 178.5(15) . . . . ? C47 C48 C49 C50 -3(3) . . . . ? O3 C49 C50 C51 -178.5(16) . . . . ? C48 C49 C50 C51 3(2) . . . . ? C47 C46 C51 C50 4(3) . . . . ? C45 C46 C51 C50 -176.5(16) . . . . ? C49 C50 C51 C46 -4(3) . . . . ? O3 C52 C53 C54 -176.4(12) . . . . ? C52 C53 C54 C55 -178.2(13) . . . . ? C53 C54 C55 C56 -178.4(13) . . . . ? C54 C55 C56 C57 175.4(14) . . . . ? C42 C43 N3 C39 -2(2) . . . . ? C40 C39 N3 C43 -1(3) . . . . ? C50 C49 O3 C52 -2(2) . . . . ? C48 C49 O3 C52 176.4(14) . . . . ? C53 C52 O3 C49 179.4(13) . . . . ? N4 C58 C59 C60 5(2) . . . . ? C58 C59 C60 C61 -4.0(19) . . . . ? C58 C59 C60 C63 179.1(13) . . . . ? C59 C60 C61 C62 3.4(19) . . . . ? C63 C60 C61 C62 -179.5(13) . . . . ? C60 C61 C62 N4 -4(2) . . . . ? C59 C60 C63 C64 -14(2) . . . . ? C61 C60 C63 C64 169.5(14) . . . . ? C60 C63 C64 C65 -177.9(13) . . . . ? C63 C64 C65 C66 3(2) . . . . ? C63 C64 C65 C70 -176.1(14) . . . . ? C70 C65 C66 C67 0(2) . . . . ? C64 C65 C66 C67 -179.3(13) . . . . ? C65 C66 C67 C68 0(2) . . . . ? C66 C67 C68 O4 180.0(12) . . . . ? C66 C67 C68 C69 0(2) . . . . ? O4 C68 C69 C70 -179.6(13) . . . . ? C67 C68 C69 C70 1(2) . . . . ? C66 C65 C70 C69 1(2) . . . . ? C64 C65 C70 C69 179.9(13) . . . . ? C68 C69 C70 C65 -1(2) . . . . ? O4 C71 C72 C73 178.6(11) . . . . ? C71 C72 C73 C74 179.6(12) . . . . ? C72 C73 C74 C75 -177.3(12) . . . . ? C73 C74 C75 C76 177.3(12) . . . . ? C59 C58 N4 C62 -5(2) . . . . ? C61 C62 N4 C58 4(2) . . . . ? C69 C68 O4 C71 -3(2) . . . . ? C67 C68 O4 C71 177.1(12) . . . . ? C72 C71 O4 C68 177.2(11) . . . . ? C82 C77 C78 F1 -179.9(12) . . . . ? I1 C77 C78 F1 -0.8(18) . . . . ? C82 C77 C78 C79 0(2) . . . . ? I1 C77 C78 C79 178.7(11) . . . . ? F1 C78 C79 C80 179.7(12) . . . . ? C77 C78 C79 C80 0(2) . . . . ? F1 C78 C79 I2 0.0(18) . . . . ? C77 C78 C79 I2 -179.5(11) . . . . ? C78 C79 C80 F2 -177.4(12) . . . . ? I2 C79 C80 F2 2.3(19) . . . . ? C78 C79 C80 C81 0(2) . . . . ? I2 C79 C80 C81 179.5(11) . . . . ? F2 C80 C81 F3 0(2) . . . . ? C79 C80 C81 F3 -176.8(13) . . . . ? F2 C80 C81 C82 177.7(12) . . . . ? C79 C80 C81 C82 0(2) . . . . ? C78 C77 C82 F4 177.9(12) . . . . ? I1 C77 C82 F4 -1.1(18) . . . . ? C78 C77 C82 C81 1(2) . . . . ? I1 C77 C82 C81 -178.5(11) . . . . ? F3 C81 C82 F4 -1(2) . . . . ? C80 C81 C82 F4 -178.0(12) . . . . ? F3 C81 C82 C77 176.7(13) . . . . ? C80 C81 C82 C77 -1(2) . . . . ? C88 C83 C84 F5 -179.7(12) . . . . ? I3 C83 C84 F5 -3.2(19) . . . . ? C88 C83 C84 C85 5(2) . . . . ? I3 C83 C84 C85 -178.2(11) . . . . ? F5 C84 C85 C86 -177.5(12) . . . . ? C83 C84 C85 C86 -3(2) . . . . ? F5 C84 C85 I4 7.4(18) . . . . ? C83 C84 C85 I4 -177.6(11) . . . . ? C84 C85 C86 F6 -179.5(12) . . . . ? I4 C85 C86 F6 -4.3(17) . . . . ? C84 C85 C86 C87 1(2) . . . . ? I4 C85 C86 C87 176.6(10) . . . . ? F6 C86 C87 F7 5.8(19) . . . . ? C85 C86 C87 F7 -175.1(12) . . . . ? F6 C86 C87 C88 177.4(12) . . . . ? C85 C86 C87 C88 -3(2) . . . . ? F7 C87 C88 F8 -2(2) . . . . ? C86 C87 C88 F8 -174.1(13) . . . . ? F7 C87 C88 C83 178.2(12) . . . . ? C86 C87 C88 C83 7(2) . . . . ? C84 C83 C88 C87 -7(2) . . . . ? I3 C83 C88 C87 176.1(11) . . . . ? C84 C83 C88 F8 173.3(13) . . . . ? I3 C83 C88 F8 -3.3(19) . . . . ? O5 C89 C90 C91 -28(3) . . . . ? C89 C90 C91 C92 15(3) . . . . ? C90 C91 C92 O5 3(3) . . . . ? C91 C92 O5 C89 -20(2) . . . . ? C90 C89 O5 C92 30(3) . . . . ? O6 C93 C94 C95 64(6) . . . . ? C93 C94 C95 C96 -58(4) . . . . ? C94 C95 C96 O6 49(6) . . . . ? C94 C93 O6 C96 -42(8) . . . . ? C95 C96 O6 C93 -17(8) . . . . ? _diffrn_measured_fraction_theta_max 0.817 _diffrn_reflns_theta_full 25.17 _diffrn_measured_fraction_theta_full 0.817 _refine_diff_density_max 4.794 _refine_diff_density_min -2.544 _refine_diff_density_rms 0.265 # Attachment 'dwb0712m.cif' data_dwb0712m _database_code_depnum_ccdc_archive 'CCDC 671521' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 N O, C6 F4 I2' _chemical_formula_sum 'C20 H13 F4 I2 N O' _chemical_formula_weight 613.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1780(4) _cell_length_b 8.0465(5) _cell_length_c 19.8272(12) _cell_angle_alpha 80.4310(10) _cell_angle_beta 86.8850(10) _cell_angle_gamma 87.1540(10) _cell_volume 969.66(10) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 6403 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 28.27 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.100 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 3.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.498 _exptl_absorpt_correction_T_max 0.790 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9869 _diffrn_reflns_av_R_equivalents 0.0802 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4743 _reflns_number_gt 4267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+1.9475P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4743 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.1319(6) 0.7324(5) 0.55980(19) 0.0226(8) Uani 1 1 d . . . C1 C 0.5835(6) 0.6925(5) 0.8865(2) 0.0166(7) Uani 1 1 d . . . C2 C 0.4708(7) 0.7179(5) 0.8263(2) 0.0170(8) Uani 1 1 d . . . C3 C 0.5506(6) 0.6658(5) 0.7666(2) 0.0163(7) Uani 1 1 d . . . C4 C 0.7532(7) 0.5832(5) 0.7681(2) 0.0173(8) Uani 1 1 d . . . C5 C 0.8712(6) 0.5569(5) 0.8265(2) 0.0180(8) Uani 1 1 d . . . C6 C 0.7861(7) 0.6116(5) 0.8851(2) 0.0167(7) Uani 1 1 d . . . F1 F 0.2734(4) 0.7981(3) 0.82691(13) 0.0210(5) Uani 1 1 d . . . F2 F 0.8384(4) 0.5243(3) 0.71256(13) 0.0236(5) Uani 1 1 d . . . F3 F 1.0661(4) 0.4747(3) 0.82683(14) 0.0235(5) Uani 1 1 d . . . F4 F 0.9050(4) 0.5852(3) 0.94067(13) 0.0225(5) Uani 1 1 d . . . I1 I 0.45375(4) 0.76865(3) 0.976245(13) 0.01876(9) Uani 1 1 d . . . I2 I 0.36999(4) 0.69853(3) 0.677913(13) 0.01813(9) Uani 1 1 d . . . C7 C 0.9303(8) 0.7994(6) 0.5546(2) 0.0256(9) Uani 1 1 d . . . H7 H 0.8644 0.8426 0.5928 0.031 Uiso 1 1 calc R . . C8 C 0.8110(7) 0.8096(6) 0.4963(2) 0.0211(8) Uani 1 1 d . . . H8 H 0.6681 0.8589 0.4953 0.025 Uiso 1 1 calc R . . C9 C 0.9027(7) 0.7470(5) 0.4397(2) 0.0185(8) Uani 1 1 d . . . C10 C 1.1137(7) 0.6756(5) 0.4454(2) 0.0195(8) Uani 1 1 d . . . H10 H 1.1831 0.6302 0.4081 0.023 Uiso 1 1 calc R . . C11 C 1.2208(7) 0.6711(6) 0.5049(2) 0.0220(8) Uani 1 1 d . . . H11 H 1.3641 0.6226 0.5073 0.026 Uiso 1 1 calc R . . C12 C 0.7963(7) 0.7503(5) 0.3753(2) 0.0192(8) Uani 1 1 d . . . H12 H 0.8686 0.6915 0.3423 0.023 Uiso 1 1 calc R . . C13 C 0.6044(7) 0.8298(5) 0.3588(2) 0.0165(7) Uani 1 1 d . . . H13 H 0.5307 0.8859 0.3924 0.020 Uiso 1 1 calc R . . C14 C 0.4983(7) 0.8377(5) 0.2933(2) 0.0156(7) Uani 1 1 d . . . C15 C 0.2967(7) 0.9185(5) 0.2826(2) 0.0176(8) Uani 1 1 d . . . H15 H 0.2274 0.9711 0.3179 0.021 Uiso 1 1 calc R . . C16 C 0.1930(7) 0.9249(5) 0.2217(2) 0.0180(8) Uani 1 1 d . . . H16 H 0.0549 0.9813 0.2156 0.022 Uiso 1 1 calc R . . C17 C 0.2928(6) 0.8483(5) 0.1697(2) 0.0157(7) Uani 1 1 d . . . C18 C 0.4960(7) 0.7652(5) 0.1795(2) 0.0162(7) Uani 1 1 d . . . H18 H 0.5648 0.7122 0.1442 0.019 Uiso 1 1 calc R . . C19 C 0.5971(6) 0.7600(5) 0.2406(2) 0.0170(8) Uani 1 1 d . . . H19 H 0.7349 0.7032 0.2468 0.020 Uiso 1 1 calc R . . C20 C 0.0029(6) 0.9286(6) 0.0940(2) 0.0216(8) Uani 1 1 d . . . H20A H 0.0204 1.0503 0.0897 0.032 Uiso 1 1 calc R . . H20B H -0.1034 0.8925 0.1314 0.032 Uiso 1 1 calc R . . H20C H -0.0480 0.9029 0.0510 0.032 Uiso 1 1 calc R . . O1 O 0.2079(5) 0.8407(4) 0.10834(15) 0.0187(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0230(19) 0.0237(18) 0.0219(18) -0.0050(14) -0.0059(14) -0.0013(15) C1 0.0141(18) 0.0132(17) 0.023(2) -0.0050(14) -0.0010(14) 0.0005(14) C2 0.0114(17) 0.0152(18) 0.024(2) -0.0030(15) -0.0034(14) 0.0033(14) C3 0.0148(18) 0.0156(18) 0.0196(19) -0.0043(14) -0.0037(14) -0.0022(14) C4 0.0154(18) 0.0175(18) 0.0202(19) -0.0069(15) 0.0007(15) -0.0019(15) C5 0.0087(17) 0.0180(19) 0.027(2) -0.0043(16) -0.0001(15) 0.0016(14) C6 0.0136(18) 0.0208(19) 0.0161(18) -0.0039(15) -0.0042(14) 0.0019(15) F1 0.0140(12) 0.0245(13) 0.0255(13) -0.0085(10) -0.0046(9) 0.0077(10) F2 0.0186(12) 0.0303(14) 0.0239(13) -0.0122(11) 0.0026(10) 0.0014(10) F3 0.0128(12) 0.0269(13) 0.0308(14) -0.0073(11) -0.0015(10) 0.0086(10) F4 0.0152(12) 0.0306(14) 0.0228(12) -0.0063(10) -0.0080(9) 0.0041(10) I1 0.01751(15) 0.02077(15) 0.01935(15) -0.00815(10) -0.00211(10) 0.00362(10) I2 0.01727(15) 0.01957(15) 0.01826(15) -0.00387(10) -0.00383(10) -0.00189(10) C7 0.027(2) 0.030(2) 0.023(2) -0.0111(18) -0.0036(17) -0.0005(18) C8 0.0151(19) 0.024(2) 0.025(2) -0.0078(17) -0.0036(16) 0.0012(16) C9 0.019(2) 0.0161(18) 0.020(2) -0.0014(15) -0.0025(15) -0.0018(15) C10 0.019(2) 0.0205(19) 0.0191(19) -0.0044(15) -0.0001(15) 0.0010(16) C11 0.019(2) 0.021(2) 0.026(2) -0.0028(16) -0.0053(16) 0.0007(16) C12 0.0173(19) 0.022(2) 0.0189(19) -0.0065(15) -0.0003(15) 0.0005(16) C13 0.0188(19) 0.0146(17) 0.0165(18) -0.0028(14) -0.0006(14) -0.0046(15) C14 0.0158(18) 0.0163(18) 0.0145(18) -0.0018(14) -0.0023(14) 0.0007(14) C15 0.0174(19) 0.0160(18) 0.0202(19) -0.0065(15) 0.0014(15) 0.0009(15) C16 0.0141(18) 0.0162(18) 0.024(2) -0.0049(15) -0.0009(15) 0.0032(14) C17 0.0126(17) 0.0148(17) 0.0192(19) -0.0013(14) -0.0014(14) 0.0006(14) C18 0.0133(18) 0.0181(18) 0.0181(18) -0.0060(14) -0.0003(14) 0.0010(14) C19 0.0113(17) 0.0166(18) 0.022(2) -0.0021(15) -0.0010(14) 0.0018(14) C20 0.0100(18) 0.030(2) 0.023(2) -0.0024(17) -0.0016(15) 0.0036(16) O1 0.0147(14) 0.0236(15) 0.0186(14) -0.0062(11) -0.0050(11) 0.0048(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. Distance for halogen bonds are O1 I1 3.080(3) N1 I2 2.801(4) ; 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 N1 C7 1.335(6) . ? N1 C11 1.348(6) . ? C1 C6 1.383(5) . ? C1 C2 1.394(6) . ? C1 I1 2.084(4) . ? C2 F1 1.352(4) . ? C2 C3 1.380(6) . ? C3 C4 1.387(6) . ? C3 I2 2.105(4) . ? C4 F2 1.341(5) . ? C4 C5 1.383(6) . ? C5 F3 1.345(4) . ? C5 C6 1.379(6) . ? C6 F4 1.338(4) . ? C7 C8 1.393(6) . ? C7 H7 0.9500 . ? C8 C9 1.387(6) . ? C8 H8 0.9500 . ? C9 C10 1.401(6) . ? C9 C12 1.464(6) . ? C10 C11 1.379(6) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.349(6) . ? C12 H12 0.9500 . ? C13 C14 1.476(5) . ? C13 H13 0.9500 . ? C14 C15 1.386(6) . ? C14 C19 1.402(6) . ? C15 C16 1.390(6) . ? C15 H15 0.9500 . ? C16 C17 1.387(6) . ? C16 H16 0.9500 . ? C17 O1 1.363(5) . ? C17 C18 1.400(5) . ? C18 C19 1.386(6) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 O1 1.439(5) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C7 N1 C11 116.8(4) . . ? C6 C1 C2 117.5(4) . . ? C6 C1 I1 120.4(3) . . ? C2 C1 I1 122.1(3) . . ? F1 C2 C3 118.6(4) . . ? F1 C2 C1 118.0(4) . . ? C3 C2 C1 123.4(4) . . ? C2 C3 C4 116.9(4) . . ? C2 C3 I2 122.2(3) . . ? C4 C3 I2 120.8(3) . . ? F2 C4 C5 118.2(4) . . ? F2 C4 C3 120.3(4) . . ? C5 C4 C3 121.5(4) . . ? F3 C5 C6 119.9(4) . . ? F3 C5 C4 120.2(4) . . ? C6 C5 C4 119.8(4) . . ? F4 C6 C5 118.4(3) . . ? F4 C6 C1 120.7(4) . . ? C5 C6 C1 120.9(4) . . ? N1 C7 C8 123.8(4) . . ? N1 C7 H7 118.1 . . ? C8 C7 H7 118.1 . . ? C9 C8 C7 119.4(4) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 116.8(4) . . ? C8 C9 C12 125.1(4) . . ? C10 C9 C12 118.1(4) . . ? C11 C10 C9 120.1(4) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N1 C11 C10 123.1(4) . . ? N1 C11 H11 118.4 . . ? C10 C11 H11 118.4 . . ? C13 C12 C9 125.6(4) . . ? C13 C12 H12 117.2 . . ? C9 C12 H12 117.2 . . ? C12 C13 C14 126.1(4) . . ? C12 C13 H13 117.0 . . ? C14 C13 H13 117.0 . . ? C15 C14 C19 118.0(4) . . ? C15 C14 C13 121.3(4) . . ? C19 C14 C13 120.7(4) . . ? C14 C15 C16 122.0(4) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C17 C16 C15 119.4(4) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? O1 C17 C16 125.8(4) . . ? O1 C17 C18 114.6(3) . . ? C16 C17 C18 119.6(4) . . ? C19 C18 C17 120.2(4) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C14 120.7(4) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? O1 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 O1 C20 117.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 -179.5(4) . . . . ? I1 C1 C2 F1 1.5(5) . . . . ? C6 C1 C2 C3 0.4(6) . . . . ? I1 C1 C2 C3 -178.6(3) . . . . ? F1 C2 C3 C4 -179.7(4) . . . . ? C1 C2 C3 C4 0.5(6) . . . . ? F1 C2 C3 I2 -2.5(5) . . . . ? C1 C2 C3 I2 177.6(3) . . . . ? C2 C3 C4 F2 178.0(4) . . . . ? I2 C3 C4 F2 0.8(5) . . . . ? C2 C3 C4 C5 -1.1(6) . . . . ? I2 C3 C4 C5 -178.3(3) . . . . ? F2 C4 C5 F3 0.2(6) . . . . ? C3 C4 C5 F3 179.2(4) . . . . ? F2 C4 C5 C6 -178.2(4) . . . . ? C3 C4 C5 C6 0.8(6) . . . . ? F3 C5 C6 F4 2.0(6) . . . . ? C4 C5 C6 F4 -179.6(4) . . . . ? F3 C5 C6 C1 -178.3(4) . . . . ? C4 C5 C6 C1 0.1(6) . . . . ? C2 C1 C6 F4 178.9(4) . . . . ? I1 C1 C6 F4 -2.0(6) . . . . ? C2 C1 C6 C5 -0.7(6) . . . . ? I1 C1 C6 C5 178.4(3) . . . . ? C11 N1 C7 C8 -0.4(7) . . . . ? N1 C7 C8 C9 0.2(7) . . . . ? C7 C8 C9 C10 0.3(6) . . . . ? C7 C8 C9 C12 -179.7(4) . . . . ? C8 C9 C10 C11 -0.5(6) . . . . ? C12 C9 C10 C11 179.4(4) . . . . ? C7 N1 C11 C10 0.1(7) . . . . ? C9 C10 C11 N1 0.3(7) . . . . ? C8 C9 C12 C13 7.4(7) . . . . ? C10 C9 C12 C13 -172.5(4) . . . . ? C9 C12 C13 C14 178.3(4) . . . . ? C12 C13 C14 C15 177.8(4) . . . . ? C12 C13 C14 C19 -0.7(6) . . . . ? C19 C14 C15 C16 -0.4(6) . . . . ? C13 C14 C15 C16 -179.0(4) . . . . ? C14 C15 C16 C17 0.1(6) . . . . ? C15 C16 C17 O1 178.1(4) . . . . ? C15 C16 C17 C18 0.2(6) . . . . ? O1 C17 C18 C19 -178.3(4) . . . . ? C16 C17 C18 C19 -0.2(6) . . . . ? C17 C18 C19 C14 -0.1(6) . . . . ? C15 C14 C19 C18 0.4(6) . . . . ? C13 C14 C19 C18 179.0(4) . . . . ? C16 C17 O1 C20 4.2(6) . . . . ? C18 C17 O1 C20 -177.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 2.776 _refine_diff_density_min -1.230 _refine_diff_density_rms 0.192