#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:11:10 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257961 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240398.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7240398 loop_ _publ_author_name 'Al-Zoubi, Raed M.' 'Al-Omari, Mothana K.' 'Al-Jammal, Walid K.' 'Ferguson, Michael J.' _publ_section_title ; Palladium-catalyzed highly regioselective mono and double Sonogashira cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under ambient conditions ; _journal_issue 28 _journal_name_full 'RSC Advances' _journal_page_first 16366 _journal_page_last 16376 _journal_paper_doi 10.1039/D0RA01569E _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C24 H10 Cl F6 I' _chemical_formula_sum 'C24 H10 Cl F6 I' _chemical_formula_weight 574.67 _chemical_name_systematic ; 5-chloro-2-iodo-1,3-bis{[4-trifluoromethyl)phenyl]ethynyl}benzene ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2020-02-05 deposited with the CCDC. 2020-04-16 downloaded from the CCDC. ; _cell_angle_alpha 91.3034(15) _cell_angle_beta 91.6389(14) _cell_angle_gamma 111.5614(14) _cell_formula_units_Z 2 _cell_length_a 9.8013(12) _cell_length_b 10.0715(12) _cell_length_c 11.7314(14) _cell_measurement_reflns_used 4048 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 26.27 _cell_measurement_theta_min 2.24 _cell_volume 1075.9(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXT-2014/5 (Sheldrick 2015)' _diffrn_ambient_temperature 193(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 8291 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.590 _diffrn_reflns_theta_min 1.738 _exptl_absorpt_coefficient_mu 1.673 _exptl_absorpt_correction_T_max 0.9260 _exptl_absorpt_correction_T_min 0.7647 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details SADABS-2016/2 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.774 _exptl_crystal_description fragment _exptl_crystal_F_000 556 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichloromethane' _exptl_crystal_size_max 0.241 _exptl_crystal_size_mid 0.122 _exptl_crystal_size_min 0.103 _refine_diff_density_max 0.504 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.077 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 4456 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0356 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.8785P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0967 _refine_ls_wR_factor_ref 0.1027 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3710 _reflns_number_total 4456 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra01569e2.cif _cod_data_source_block jus1803 _cod_depositor_comments 'Adding full bibliography for 7240398--7240401.cif.' _cod_database_code 7240398 _shelx_shelxl_version_number 2017/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.689 _shelx_estimated_absorpt_t_max 0.847 _shelx_res_file ; TITL jus1803 in P-1 jus1803.res created by SHELXL-2017/1 at 10:47:51 on 24-Sep-2018 CELL 0.71073 9.80130 10.07150 11.73140 91.3034 91.6389 111.5614 ZERR 2.00 0.00120 0.00120 0.00140 0.0015 0.0014 0.0014 LATT 1 SFAC C H F CL I UNIT 48 20 12 2 2 TEMP -80 SIZE 0.103 0.122 0.241 L.S. 4 ACTA CONF WGHT 0.051000 0.878500 FVAR 0.12304 I1 5 0.331584 0.651151 0.253993 11.00000 0.06492 0.05985 = 0.05778 -0.00224 -0.00423 0.03966 CL1 4 -0.053185 1.065067 0.220571 11.00000 0.05676 0.05469 = 0.06325 -0.00880 -0.00794 0.03702 F1 3 0.548566 0.671675 0.992628 11.00000 0.05682 0.09328 = 0.06637 0.04573 -0.00747 0.01111 F2 3 0.759306 0.769374 0.924987 11.00000 0.05185 0.10850 = 0.06422 0.02777 -0.00600 0.03708 F3 3 0.667656 0.895262 1.017644 11.00000 0.11932 0.10116 = 0.05015 -0.01529 -0.04331 0.05519 F4 3 0.325425 0.411607 -0.497157 11.00000 0.09430 0.06207 = 0.07865 -0.01014 0.05006 0.01777 F5 3 0.095199 0.296642 -0.516919 11.00000 0.09636 0.11702 = 0.05367 -0.04716 -0.01537 0.04651 F6 3 0.226167 0.210441 -0.420657 11.00000 0.12484 0.04976 = 0.06919 -0.01043 0.02457 0.04312 C1 1 0.203592 0.865606 0.339319 11.00000 0.02909 0.03173 = 0.02725 -0.00161 -0.00425 0.00712 C2 1 0.212185 0.783776 0.242985 11.00000 0.03148 0.03142 = 0.03081 -0.00155 -0.00152 0.01203 C3 1 0.140690 0.791079 0.139608 11.00000 0.03085 0.02924 = 0.02848 -0.00345 -0.00191 0.00818 C4 1 0.058440 0.879255 0.134213 11.00000 0.03547 0.03542 = 0.03148 -0.00325 -0.00876 0.01330 AFIX 43 H4 2 0.007930 0.884074 0.065037 11.00000 -1.20000 AFIX 0 C5 1 0.050946 0.958549 0.228865 11.00000 0.03099 0.03104 = 0.04436 -0.00360 -0.00353 0.01589 C6 1 0.122097 0.953307 0.331172 11.00000 0.03578 0.03296 = 0.03222 -0.00822 -0.00254 0.01153 AFIX 43 H6 2 0.115507 1.009177 0.395615 11.00000 -1.20000 AFIX 0 C7 1 0.277594 0.860681 0.445773 11.00000 0.03407 0.04079 = 0.03010 -0.00258 -0.00368 0.01019 C8 1 0.339916 0.857916 0.533601 11.00000 0.03405 0.04299 = 0.03285 -0.00172 0.00003 0.01124 C9 1 0.148179 0.711015 0.038819 11.00000 0.03750 0.03384 = 0.03299 -0.00250 -0.00127 0.01172 C10 1 0.152439 0.645757 -0.046336 11.00000 0.03811 0.03396 = 0.03381 -0.00144 0.00055 0.01020 C11 1 0.418379 0.846783 0.636273 11.00000 0.03001 0.03643 = 0.02736 0.00150 -0.00205 0.00790 C12 1 0.420664 0.926466 0.735369 11.00000 0.03927 0.04250 = 0.03484 -0.00500 -0.00434 0.02110 AFIX 43 H12 2 0.372872 0.993197 0.735534 11.00000 -1.20000 AFIX 0 C13 1 0.492426 0.908472 0.833423 11.00000 0.04313 0.05102 = 0.02741 -0.00733 -0.00415 0.02138 AFIX 43 H13 2 0.493120 0.962492 0.901033 11.00000 -1.20000 AFIX 0 C14 1 0.562787 0.813055 0.833900 11.00000 0.03406 0.03877 = 0.03072 0.00308 -0.00550 0.01024 C15 1 0.564049 0.735160 0.735678 11.00000 0.04748 0.04045 = 0.04539 -0.00100 -0.00631 0.02458 AFIX 43 H15 2 0.614870 0.670985 0.735828 11.00000 -1.20000 AFIX 0 C16 1 0.491114 0.750774 0.637002 11.00000 0.04527 0.04298 = 0.03329 -0.00871 -0.00154 0.01888 AFIX 43 H16 2 0.490584 0.696131 0.569793 11.00000 -1.20000 AFIX 0 C17 1 0.633749 0.787272 0.941629 11.00000 0.04691 0.05524 = 0.04011 0.00764 -0.00719 0.01643 C21 1 0.161732 0.563568 -0.145393 11.00000 0.03343 0.02988 = 0.02919 -0.00520 0.00036 0.00816 C22 1 0.101043 0.578850 -0.250499 11.00000 0.05314 0.03711 = 0.04128 -0.00885 -0.00697 0.02564 AFIX 43 H22 2 0.050579 0.642960 -0.257173 11.00000 -1.20000 AFIX 0 C23 1 0.113963 0.500956 -0.345338 11.00000 0.06033 0.04830 = 0.02874 -0.00693 -0.01086 0.02482 AFIX 43 H23 2 0.072076 0.511694 -0.416921 11.00000 -1.20000 AFIX 0 C24 1 0.186993 0.408056 -0.336824 11.00000 0.03658 0.03438 = 0.03638 -0.00752 0.00468 0.00973 C25 1 0.246962 0.390848 -0.233075 11.00000 0.04401 0.03886 = 0.04753 -0.00415 0.00195 0.02220 AFIX 43 H25 2 0.296429 0.325840 -0.226874 11.00000 -1.20000 AFIX 0 C26 1 0.234502 0.469418 -0.137477 11.00000 0.04866 0.04062 = 0.03148 -0.00178 -0.00510 0.02012 AFIX 43 H26 2 0.276421 0.458271 -0.066027 11.00000 -1.20000 AFIX 0 C27 1 0.208212 0.331569 -0.441945 11.00000 0.05798 0.04650 = 0.04589 -0.01075 0.01297 0.01469 HKLF 4 REM jus1803 in P-1 REM R1 = 0.0356 for 3710 Fo > 4sig(Fo) and 0.0441 for all 4456 data REM 289 parameters refined using 0 restraints END WGHT 0.0510 0.8770 REM Highest difference peak 0.504, deepest hole -0.518, 1-sigma level 0.077 Q1 1 0.0042 1.0399 0.2362 11.00000 0.05 0.50 Q2 1 -0.0812 1.0529 0.2691 11.00000 0.05 0.48 Q3 1 0.5579 0.8237 1.0305 11.00000 0.05 0.42 Q4 1 0.3746 0.3716 -0.4363 11.00000 0.05 0.40 Q5 1 0.0945 0.8218 0.1449 11.00000 0.05 0.38 Q6 1 0.7286 0.8700 0.9811 11.00000 0.05 0.37 Q7 1 0.1675 0.7824 0.1816 11.00000 0.05 0.36 Q8 1 0.1743 0.9215 0.3313 11.00000 0.05 0.34 Q9 1 0.0632 0.9381 0.2812 11.00000 0.05 0.33 Q10 1 0.1988 0.3949 -0.5374 11.00000 0.05 0.32 Q11 1 0.1239 0.5603 -0.1926 11.00000 0.05 0.32 Q12 1 0.4495 0.8033 0.6506 11.00000 0.05 0.31 Q13 1 0.2164 0.3952 -0.3741 11.00000 0.05 0.31 Q14 1 0.5004 0.7195 0.9995 11.00000 0.05 0.30 Q15 1 0.4484 0.9028 0.6768 11.00000 0.05 0.29 Q16 1 0.2806 0.7651 0.7180 11.00000 0.05 0.29 Q17 1 0.2459 0.4372 -0.1786 11.00000 0.05 0.29 Q18 1 0.3207 0.2683 -0.4001 11.00000 0.05 0.29 Q19 1 0.6836 0.6769 0.9197 11.00000 0.05 0.28 Q20 1 0.2322 0.4230 -0.2972 11.00000 0.05 0.27 ; _shelx_res_checksum 8656 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.33158(3) 0.65115(3) 0.25399(2) 0.05633(12) Uani 1 1 d . . . . . Cl1 Cl -0.05318(11) 1.06507(11) 0.22057(9) 0.0539(2) Uani 1 1 d . . . . . F1 F 0.5486(3) 0.6717(3) 0.9926(2) 0.0763(8) Uani 1 1 d . . . . . F2 F 0.7593(3) 0.7694(3) 0.9250(2) 0.0725(8) Uani 1 1 d . . . . . F3 F 0.6677(4) 0.8953(3) 1.0176(2) 0.0873(9) Uani 1 1 d . . . . . F4 F 0.3254(3) 0.4116(3) -0.4972(2) 0.0807(9) Uani 1 1 d . . . . . F5 F 0.0952(4) 0.2966(4) -0.5169(2) 0.0882(10) Uani 1 1 d . . . . . F6 F 0.2262(4) 0.2104(3) -0.4207(2) 0.0779(8) Uani 1 1 d . . . . . C1 C 0.2036(3) 0.8656(3) 0.3393(2) 0.0307(6) Uani 1 1 d . . . . . C2 C 0.2122(3) 0.7838(3) 0.2430(3) 0.0312(6) Uani 1 1 d . . . . . C3 C 0.1407(3) 0.7911(3) 0.1396(3) 0.0305(6) Uani 1 1 d . . . . . C4 C 0.0584(4) 0.8793(3) 0.1342(3) 0.0343(7) Uani 1 1 d . . . . . H4 H 0.007930 0.884074 0.065037 0.041 Uiso 1 1 calc R U . . . C5 C 0.0509(3) 0.9585(3) 0.2289(3) 0.0344(7) Uani 1 1 d . . . . . C6 C 0.1221(4) 0.9533(3) 0.3312(3) 0.0342(7) Uani 1 1 d . . . . . H6 H 0.115507 1.009177 0.395615 0.041 Uiso 1 1 calc R U . . . C7 C 0.2776(4) 0.8607(4) 0.4458(3) 0.0362(7) Uani 1 1 d . . . . . C8 C 0.3399(4) 0.8579(4) 0.5336(3) 0.0375(7) Uani 1 1 d . . . . . C9 C 0.1482(4) 0.7110(3) 0.0388(3) 0.0353(7) Uani 1 1 d . . . . . C10 C 0.1524(4) 0.6458(4) -0.0463(3) 0.0362(7) Uani 1 1 d . . . . . C11 C 0.4184(3) 0.8468(3) 0.6363(3) 0.0326(7) Uani 1 1 d . . . . . C12 C 0.4207(4) 0.9265(4) 0.7354(3) 0.0374(7) Uani 1 1 d . . . . . H12 H 0.372872 0.993197 0.735534 0.045 Uiso 1 1 calc R U . . . C13 C 0.4924(4) 0.9085(4) 0.8334(3) 0.0396(8) Uani 1 1 d . . . . . H13 H 0.493120 0.962492 0.901033 0.048 Uiso 1 1 calc R U . . . C14 C 0.5628(4) 0.8131(4) 0.8339(3) 0.0355(7) Uani 1 1 d . . . . . C15 C 0.5640(4) 0.7352(4) 0.7357(3) 0.0423(8) Uani 1 1 d . . . . . H15 H 0.614870 0.670985 0.735828 0.051 Uiso 1 1 calc R U . . . C16 C 0.4911(4) 0.7508(4) 0.6370(3) 0.0400(8) Uani 1 1 d . . . . . H16 H 0.490584 0.696131 0.569793 0.048 Uiso 1 1 calc R U . . . C17 C 0.6337(4) 0.7873(4) 0.9416(3) 0.0482(9) Uani 1 1 d . . . . . C21 C 0.1617(3) 0.5636(3) -0.1454(3) 0.0319(7) Uani 1 1 d . . . . . C22 C 0.1010(4) 0.5789(4) -0.2505(3) 0.0416(8) Uani 1 1 d . . . . . H22 H 0.050579 0.642960 -0.257173 0.050 Uiso 1 1 calc R U . . . C23 C 0.1140(4) 0.5010(4) -0.3453(3) 0.0448(9) Uani 1 1 d . . . . . H23 H 0.072076 0.511694 -0.416921 0.054 Uiso 1 1 calc R U . . . C24 C 0.1870(4) 0.4081(4) -0.3368(3) 0.0368(7) Uani 1 1 d . . . . . C25 C 0.2470(4) 0.3908(4) -0.2331(3) 0.0416(8) Uani 1 1 d . . . . . H25 H 0.296429 0.325840 -0.226874 0.050 Uiso 1 1 calc R U . . . C26 C 0.2345(4) 0.4694(4) -0.1375(3) 0.0394(8) Uani 1 1 d . . . . . H26 H 0.276421 0.458271 -0.066027 0.047 Uiso 1 1 calc R U . . . C27 C 0.2082(5) 0.3316(4) -0.4419(3) 0.0514(10) 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 I1 0.0649(2) 0.05985(19) 0.05778(18) -0.00224(13) -0.00423(13) 0.03966(15) Cl1 0.0568(6) 0.0547(6) 0.0632(6) -0.0088(4) -0.0079(5) 0.0370(5) F1 0.0568(15) 0.093(2) 0.0664(16) 0.0457(15) -0.0075(12) 0.0111(14) F2 0.0518(15) 0.108(2) 0.0642(15) 0.0278(15) -0.0060(12) 0.0371(15) F3 0.119(3) 0.101(2) 0.0502(14) -0.0153(14) -0.0433(15) 0.0552(19) F4 0.094(2) 0.0621(16) 0.0786(18) -0.0101(13) 0.0501(16) 0.0178(15) F5 0.096(2) 0.117(2) 0.0537(15) -0.0472(16) -0.0154(14) 0.0465(19) F6 0.125(2) 0.0498(14) 0.0692(16) -0.0104(12) 0.0246(16) 0.0431(16) C1 0.0291(16) 0.0317(16) 0.0273(14) -0.0016(12) -0.0043(12) 0.0071(13) C2 0.0315(16) 0.0314(16) 0.0308(15) -0.0015(12) -0.0015(12) 0.0120(13) C3 0.0308(16) 0.0292(15) 0.0285(14) -0.0035(12) -0.0019(12) 0.0082(13) C4 0.0355(17) 0.0354(17) 0.0315(15) -0.0033(13) -0.0088(13) 0.0133(14) C5 0.0310(16) 0.0310(16) 0.0444(18) -0.0036(13) -0.0035(13) 0.0159(13) C6 0.0358(17) 0.0330(16) 0.0322(16) -0.0082(13) -0.0025(13) 0.0115(14) C7 0.0341(17) 0.0408(18) 0.0301(16) -0.0026(13) -0.0037(13) 0.0102(14) C8 0.0341(17) 0.0430(19) 0.0329(16) -0.0017(14) 0.0000(13) 0.0112(15) C9 0.0375(18) 0.0338(17) 0.0330(16) -0.0025(13) -0.0013(13) 0.0117(14) C10 0.0381(18) 0.0340(17) 0.0338(16) -0.0014(13) 0.0006(13) 0.0102(14) C11 0.0300(16) 0.0364(17) 0.0274(14) 0.0015(12) -0.0021(12) 0.0079(13) C12 0.0393(18) 0.0425(18) 0.0348(16) -0.0050(14) -0.0043(14) 0.0211(15) C13 0.0431(19) 0.051(2) 0.0274(15) -0.0073(14) -0.0041(14) 0.0214(17) C14 0.0341(17) 0.0388(18) 0.0307(15) 0.0031(13) -0.0055(13) 0.0102(14) C15 0.047(2) 0.0405(19) 0.0454(19) -0.0010(15) -0.0063(16) 0.0246(16) C16 0.045(2) 0.0430(19) 0.0333(16) -0.0087(14) -0.0015(14) 0.0189(16) C17 0.047(2) 0.055(2) 0.0401(19) 0.0076(17) -0.0072(16) 0.0164(18) C21 0.0334(16) 0.0299(15) 0.0292(15) -0.0052(12) 0.0004(12) 0.0082(13) C22 0.053(2) 0.0371(18) 0.0413(18) -0.0089(14) -0.0070(16) 0.0256(17) C23 0.060(2) 0.048(2) 0.0287(16) -0.0069(15) -0.0109(15) 0.0248(18) C24 0.0366(18) 0.0344(17) 0.0364(17) -0.0075(14) 0.0047(14) 0.0097(14) C25 0.044(2) 0.0389(18) 0.0475(19) -0.0041(15) 0.0019(16) 0.0222(16) C26 0.049(2) 0.0406(18) 0.0315(16) -0.0018(14) -0.0051(14) 0.0201(16) C27 0.058(2) 0.046(2) 0.046(2) -0.0108(17) 0.0130(18) 0.0147(19) 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' F F 0.0171 0.0103 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.3(3) . . ? C6 C1 C7 119.5(3) . . ? C2 C1 C7 121.2(3) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 I1 119.8(2) . . ? C1 C2 I1 119.9(2) . . ? C2 C3 C4 119.0(3) . . ? C2 C3 C9 122.3(3) . . ? C4 C3 C9 118.7(3) . . ? C5 C4 C3 120.0(3) . . ? C4 C5 C6 121.6(3) . . ? C4 C5 Cl1 119.2(2) . . ? C6 C5 Cl1 119.3(2) . . ? C5 C6 C1 119.7(3) . . ? C8 C7 C1 179.3(4) . . ? C7 C8 C11 175.9(4) . . ? C10 C9 C3 178.5(4) . . ? C9 C10 C21 177.0(4) . . ? C12 C11 C16 119.3(3) . . ? C12 C11 C8 121.8(3) . . ? C16 C11 C8 118.9(3) . . ? C13 C12 C11 120.0(3) . . ? C14 C13 C12 120.5(3) . . ? C13 C14 C15 120.3(3) . . ? C13 C14 C17 120.7(3) . . ? C15 C14 C17 119.0(3) . . ? C14 C15 C16 119.9(3) . . ? C15 C16 C11 120.0(3) . . ? F1 C17 F2 106.2(3) . . ? F1 C17 F3 106.8(3) . . ? F2 C17 F3 104.9(3) . . ? F1 C17 C14 112.2(3) . . ? F2 C17 C14 113.2(3) . . ? F3 C17 C14 112.9(3) . . ? C26 C21 C22 119.0(3) . . ? C26 C21 C10 119.9(3) . . ? C22 C21 C10 121.1(3) . . ? C23 C22 C21 120.1(3) . . ? C24 C23 C22 120.5(3) . . ? C23 C24 C25 120.1(3) . . ? C23 C24 C27 119.7(3) . . ? C25 C24 C27 120.1(3) . . ? C24 C25 C26 119.5(3) . . ? C21 C26 C25 120.7(3) . . ? F6 C27 F5 105.5(3) . . ? F6 C27 F4 106.7(3) . . ? F5 C27 F4 106.1(4) . . ? F6 C27 C24 113.4(3) . . ? F5 C27 C24 113.0(3) . . ? F4 C27 C24 111.6(3) . . ? 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 I1 C2 2.078(3) . ? Cl1 C5 1.734(3) . ? F1 C17 1.325(5) . ? F2 C17 1.327(5) . ? F3 C17 1.327(5) . ? F4 C27 1.332(5) . ? F5 C27 1.330(5) . ? F6 C27 1.323(5) . ? C1 C6 1.395(5) . ? C1 C2 1.406(4) . ? C1 C7 1.437(4) . ? C2 C3 1.400(4) . ? C3 C4 1.403(4) . ? C3 C9 1.435(4) . ? C4 C5 1.372(4) . ? C5 C6 1.383(5) . ? C7 C8 1.189(5) . ? C8 C11 1.439(4) . ? C9 C10 1.193(4) . ? C10 C21 1.436(4) . ? C11 C12 1.392(4) . ? C11 C16 1.396(5) . ? C12 C13 1.381(5) . ? C13 C14 1.373(5) . ? C14 C15 1.382(5) . ? C14 C17 1.499(5) . ? C15 C16 1.385(5) . ? C21 C26 1.383(5) . ? C21 C22 1.390(5) . ? C22 C23 1.382(5) . ? C23 C24 1.375(5) . ? C24 C25 1.379(5) . ? C24 C27 1.499(5) . ? C25 C26 1.392(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 C6 C1 C2 C3 0.5(5) . . . . ? C7 C1 C2 C3 -179.3(3) . . . . ? C6 C1 C2 I1 -179.5(2) . . . . ? C7 C1 C2 I1 0.7(4) . . . . ? C1 C2 C3 C4 -1.1(5) . . . . ? I1 C2 C3 C4 178.9(2) . . . . ? C1 C2 C3 C9 179.1(3) . . . . ? I1 C2 C3 C9 -0.9(4) . . . . ? C2 C3 C4 C5 1.1(5) . . . . ? C9 C3 C4 C5 -179.1(3) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? C3 C4 C5 Cl1 -179.2(3) . . . . ? C4 C5 C6 C1 -0.1(5) . . . . ? Cl1 C5 C6 C1 178.7(2) . . . . ? C2 C1 C6 C5 0.1(5) . . . . ? C7 C1 C6 C5 179.9(3) . . . . ? C16 C11 C12 C13 -1.0(5) . . . . ? C8 C11 C12 C13 177.4(3) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C12 C13 C14 C15 0.8(5) . . . . ? C12 C13 C14 C17 -176.6(3) . . . . ? C13 C14 C15 C16 -1.5(5) . . . . ? C17 C14 C15 C16 175.9(3) . . . . ? C14 C15 C16 C11 1.0(5) . . . . ? C12 C11 C16 C15 0.2(5) . . . . ? C8 C11 C16 C15 -178.2(3) . . . . ? C13 C14 C17 F1 97.8(4) . . . . ? C15 C14 C17 F1 -79.7(5) . . . . ? C13 C14 C17 F2 -142.0(4) . . . . ? C15 C14 C17 F2 40.6(5) . . . . ? C13 C14 C17 F3 -23.0(5) . . . . ? C15 C14 C17 F3 159.5(4) . . . . ? C26 C21 C22 C23 -0.1(5) . . . . ? C10 C21 C22 C23 178.6(3) . . . . ? C21 C22 C23 C24 -0.1(6) . . . . ? C22 C23 C24 C25 0.6(6) . . . . ? C22 C23 C24 C27 -176.1(4) . . . . ? C23 C24 C25 C26 -0.8(5) . . . . ? C27 C24 C25 C26 175.9(3) . . . . ? C22 C21 C26 C25 0.0(5) . . . . ? C10 C21 C26 C25 -178.8(3) . . . . ? C24 C25 C26 C21 0.5(5) . . . . ? C23 C24 C27 F6 -155.4(4) . . . . ? C25 C24 C27 F6 27.9(5) . . . . ? C23 C24 C27 F5 -35.4(5) . . . . ? C25 C24 C27 F5 147.9(4) . . . . ? C23 C24 C27 F4 84.0(5) . . . . ? C25 C24 C27 F4 -92.7(4) . . . . ?