#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:11:10 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257961 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240399.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_7240399 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 'C15 H7 F3 I2' _chemical_formula_sum 'C15 H7 F3 I2' _chemical_formula_weight 498.01 _chemical_name_systematic ; 1,2-diiodo-3-{[4-(trifluoromethyl)phenyl]ethynyl}benzene ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 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 90 _cell_angle_beta 90.1567(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.1687(8) _cell_length_b 4.3193(3) _cell_length_c 27.7962(17) _cell_measurement_reflns_used 9886 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 30.51 _cell_measurement_theta_min 2.22 _cell_volume 1460.97(17) _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 (Sheldrick 2015)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.0171 _diffrn_reflns_av_unetI/netI 0.0138 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 16567 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.530 _diffrn_reflns_theta_min 1.465 _exptl_absorpt_coefficient_mu 4.324 _exptl_absorpt_correction_T_max 0.3623 _exptl_absorpt_correction_T_min 0.2634 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.264 _exptl_crystal_description block _exptl_crystal_F_000 920 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: hexanes/dichloromethane' _exptl_crystal_size_max 0.185 _exptl_crystal_size_mid 0.183 _exptl_crystal_size_min 0.119 _refine_diff_density_max 1.059 _refine_diff_density_min -0.795 _refine_diff_density_rms 0.094 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 4473 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.161 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0250 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+1.1974P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.0575 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4127 _reflns_number_total 4473 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra01569e2.cif _cod_data_source_block jus1808 _cod_depositor_comments 'Adding full bibliography for 7240398--7240401.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240399 _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 0.502 _shelx_estimated_absorpt_t_max 0.627 _shelx_res_file ; TITL jus1808 in P2(1)/c jus1808.res created by SHELXL-2017/1 at 14:54:31 on 05-Dec-2018 CELL 0.71073 12.16870 4.31930 27.79620 90.0000 90.1567 90.0000 ZERR 4.00 0.00080 0.00030 0.00170 0.0000 0.0009 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H F I UNIT 60 28 12 8 TEMP -100.000 SIZE 0.119 0.183 0.185 L.S. 12 ACTA CONF WGHT 0.024100 1.197400 FVAR 0.07900 0.50238 I1 4 0.574360 0.089744 0.929831 11.00000 0.03233 0.03586 = 0.03837 0.00274 -0.00175 0.00537 I2 4 0.470384 0.042058 0.807110 11.00000 0.04156 0.03051 = 0.02917 -0.00087 0.00960 0.00302 PART 1 F1A 3 -0.017634 0.528178 0.555731 21.00000 0.05718 0.09345 = 0.03962 0.00998 -0.00750 0.01960 F2A 3 0.145645 0.381187 0.536141 21.00000 0.05080 0.10011 = 0.03263 0.00846 0.01471 -0.00188 F3A 3 0.020813 0.050216 0.554311 21.00000 0.08837 0.07474 = 0.04238 -0.01380 -0.00922 -0.02044 PART 2 F1B 3 -0.004418 0.367500 0.552147 -21.00000 0.04301 0.16807 = 0.03478 0.01127 -0.01110 -0.04876 F2B 3 0.159006 0.522946 0.541647 -21.00000 0.05247 0.08637 = 0.03735 0.01678 0.00224 -0.02315 F3B 3 0.126147 0.041933 0.544452 -21.00000 0.19828 0.07680 = 0.04030 -0.02213 -0.00298 0.00094 PART 0 C1 1 0.420638 0.267346 0.909824 11.00000 0.02688 0.02326 = 0.03149 0.00253 0.00217 -0.00162 C2 1 0.381291 0.249552 0.862770 11.00000 0.02904 0.02256 = 0.02772 0.00124 0.00587 -0.00323 C3 1 0.277837 0.379112 0.851826 11.00000 0.02885 0.03233 = 0.03005 0.00137 0.00148 -0.00266 C4 1 0.217599 0.524861 0.888237 11.00000 0.02931 0.04470 = 0.03901 -0.00148 0.00170 0.00378 AFIX 43 H4 2 0.148358 0.615176 0.880922 11.00000 -1.20000 AFIX 0 C5 1 0.258014 0.538471 0.934738 11.00000 0.03707 0.05132 = 0.03383 -0.00844 0.00654 0.00774 AFIX 43 H5 2 0.216279 0.636256 0.959251 11.00000 -1.20000 AFIX 0 C6 1 0.359284 0.409623 0.945578 11.00000 0.03702 0.04045 = 0.02759 -0.00315 0.00160 0.00326 AFIX 43 H6 2 0.386839 0.418613 0.977558 11.00000 -1.20000 AFIX 0 C7 1 0.233800 0.369250 0.803819 11.00000 0.03151 0.03852 = 0.03704 0.00124 -0.00043 -0.00144 C8 1 0.198571 0.362580 0.763856 11.00000 0.03065 0.03992 = 0.03689 0.00035 -0.00020 -0.00218 C9 1 0.164886 0.347567 0.714263 11.00000 0.02892 0.03534 = 0.03141 0.00053 0.00052 -0.00835 C10 1 0.228282 0.177440 0.681848 11.00000 0.02846 0.04181 = 0.04718 -0.00332 0.00353 -0.00366 AFIX 43 H10 2 0.291283 0.067694 0.692721 11.00000 -1.20000 AFIX 0 C11 1 0.198373 0.169959 0.633412 11.00000 0.04660 0.04439 = 0.04322 -0.01013 0.01581 -0.01027 AFIX 43 H11 2 0.241337 0.055183 0.611187 11.00000 -1.20000 AFIX 0 C12 1 0.106793 0.328215 0.617602 11.00000 0.05285 0.04163 = 0.02882 0.00105 0.00120 -0.02001 C13 1 0.042369 0.493560 0.649612 11.00000 0.03989 0.04260 = 0.03662 0.00610 -0.00693 -0.00694 AFIX 43 H13 2 -0.021146 0.600429 0.638620 11.00000 -1.20000 AFIX 0 C14 1 0.071549 0.501426 0.697835 11.00000 0.03490 0.04079 = 0.03198 -0.00062 0.00111 0.00006 AFIX 43 H14 2 0.027300 0.613203 0.719944 11.00000 -1.20000 AFIX 0 PART 1 C15A 1 0.059013 0.328745 0.565701 21.00000 0.03898 0.05230 = 0.03388 0.00289 0.00928 -0.01068 PART 2 C15B 1 0.098869 0.316089 0.563891 -21.00000 0.05601 0.05523 = 0.03062 -0.00281 0.00257 -0.02166 PART 0 HKLF 4 REM jus1808 in P2(1)/c REM R1 = 0.0250 for 4127 Fo > 4sig(Fo) and 0.0281 for all 4473 data REM 218 parameters refined using 0 restraints END WGHT 0.0241 1.2414 REM Highest difference peak 1.059, deepest hole -0.795, 1-sigma level 0.094 Q1 1 0.5707 0.0912 0.9008 11.00000 0.05 1.06 Q2 1 0.4731 0.0454 0.8370 11.00000 0.05 0.90 Q3 1 0.4597 0.0190 0.7778 11.00000 0.05 0.74 Q4 1 0.5902 0.1145 0.9625 11.00000 0.05 0.63 Q5 1 0.4229 0.0482 0.7884 11.00000 0.05 0.59 Q6 1 0.5251 0.1431 0.8123 11.00000 0.05 0.58 Q7 1 0.6169 0.0336 0.9478 11.00000 0.05 0.49 Q8 1 0.5051 -0.0949 0.8029 11.00000 0.05 0.47 Q9 1 0.5148 0.0746 0.9390 11.00000 0.05 0.47 Q10 1 0.4704 0.2298 0.8068 11.00000 0.05 0.45 Q11 1 0.4261 -0.1510 0.8109 11.00000 0.05 0.44 Q12 1 0.3892 0.2210 0.8873 11.00000 0.05 0.44 Q13 1 0.6035 -0.0828 0.9225 11.00000 0.05 0.41 Q14 1 0.2106 0.1971 0.6584 11.00000 0.05 0.40 Q15 1 0.3303 0.2985 0.8569 11.00000 0.05 0.40 Q16 1 0.5007 0.1368 0.9228 11.00000 0.05 0.39 Q17 1 0.0877 0.3395 0.5972 11.00000 0.05 0.39 Q18 1 0.5737 0.2878 0.9283 11.00000 0.05 0.39 Q19 1 0.2478 0.5590 0.9096 11.00000 0.05 0.37 Q20 1 0.1800 0.3162 0.7382 11.00000 0.05 0.37 ; _shelx_res_checksum 89203 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 0.57436(2) 0.08974(4) 0.92983(2) 0.03552(5) Uani 1 1 d . . . . . I2 I 0.47038(2) 0.04206(4) 0.80711(2) 0.03373(5) Uani 1 1 d . . . . . F1A F -0.0176(7) 0.5282(19) 0.5557(3) 0.063(2) Uani 0.502(10) 1 d . . P A 1 F2A F 0.1456(7) 0.381(2) 0.5361(3) 0.061(2) Uani 0.502(10) 1 d . . P A 1 F3A F 0.0208(6) 0.0502(14) 0.55431(17) 0.069(2) Uani 0.502(10) 1 d . . P A 1 F1B F -0.0044(7) 0.367(3) 0.5521(3) 0.082(4) Uani 0.498(10) 1 d . . P A 2 F2B F 0.1590(7) 0.523(2) 0.5416(3) 0.0587(19) Uani 0.498(10) 1 d . . P A 2 F3B F 0.1261(10) 0.0419(14) 0.54445(18) 0.105(4) Uani 0.498(10) 1 d . . P A 2 C1 C 0.42064(19) 0.2673(5) 0.90982(8) 0.0272(4) Uani 1 1 d . . . . . C2 C 0.38129(19) 0.2496(5) 0.86277(8) 0.0264(4) Uani 1 1 d . . . . . C3 C 0.2778(2) 0.3791(6) 0.85183(9) 0.0304(5) Uani 1 1 d . . . . . C4 C 0.2176(2) 0.5249(7) 0.88824(10) 0.0377(6) Uani 1 1 d . . . . . H4 H 0.148358 0.615176 0.880922 0.045 Uiso 1 1 calc R U . . . C5 C 0.2580(2) 0.5385(7) 0.93474(10) 0.0407(6) Uani 1 1 d . . . . . H5 H 0.216279 0.636256 0.959251 0.049 Uiso 1 1 calc R U . . . C6 C 0.3593(2) 0.4096(6) 0.94558(9) 0.0350(5) Uani 1 1 d . . . . . H6 H 0.386839 0.418613 0.977558 0.042 Uiso 1 1 calc R U . . . C7 C 0.2338(2) 0.3693(7) 0.80382(10) 0.0357(5) Uani 1 1 d . . . . . C8 C 0.1986(2) 0.3626(7) 0.76386(10) 0.0358(5) Uani 1 1 d . . . . . C9 C 0.1649(2) 0.3476(6) 0.71426(9) 0.0319(5) Uani 1 1 d . . . . . C10 C 0.2283(2) 0.1774(7) 0.68185(10) 0.0391(6) Uani 1 1 d . . . . . H10 H 0.291283 0.067694 0.692721 0.047 Uiso 1 1 calc R U . . . C11 C 0.1984(3) 0.1700(7) 0.63341(11) 0.0447(7) Uani 1 1 d . . . . . H11 H 0.241337 0.055183 0.611187 0.054 Uiso 1 1 calc R U . . . C12 C 0.1068(3) 0.3282(7) 0.61760(9) 0.0411(6) Uani 1 1 d . . . . . C13 C 0.0424(2) 0.4936(7) 0.64961(10) 0.0397(6) Uani 1 1 d . . . . . H13 H -0.021146 0.600429 0.638620 0.048 Uiso 1 1 calc R U . . . C14 C 0.0715(2) 0.5014(7) 0.69783(10) 0.0359(5) Uani 1 1 d . . . . . H14 H 0.027300 0.613203 0.719944 0.043 Uiso 1 1 calc R U . . . C15A C 0.0590(9) 0.329(4) 0.5657(6) 0.042(2) Uani 0.502(10) 1 d . . P A 1 C15B C 0.0989(12) 0.316(4) 0.5639(5) 0.047(3) Uani 0.498(10) 1 d . . P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03233(9) 0.03586(9) 0.03837(9) 0.00274(6) -0.00175(6) 0.00537(6) I2 0.04156(10) 0.03051(8) 0.02917(8) -0.00087(6) 0.00960(6) 0.00302(6) F1A 0.057(3) 0.093(5) 0.040(3) 0.010(3) -0.008(2) 0.020(4) F2A 0.051(3) 0.100(6) 0.033(2) 0.008(4) 0.015(2) -0.002(4) F3A 0.088(5) 0.075(4) 0.042(2) -0.014(2) -0.009(2) -0.020(3) F1B 0.043(4) 0.168(12) 0.035(3) 0.011(5) -0.011(3) -0.049(5) F2B 0.052(3) 0.086(5) 0.037(3) 0.017(3) 0.002(2) -0.023(3) F3B 0.198(11) 0.077(4) 0.040(3) -0.022(2) -0.003(4) 0.001(4) C1 0.0269(10) 0.0233(10) 0.0315(11) 0.0025(8) 0.0022(8) -0.0016(8) C2 0.0290(11) 0.0226(10) 0.0277(10) 0.0012(8) 0.0059(8) -0.0032(8) C3 0.0288(11) 0.0323(12) 0.0300(11) 0.0014(9) 0.0015(9) -0.0027(9) C4 0.0293(12) 0.0447(15) 0.0390(14) -0.0015(11) 0.0017(10) 0.0038(11) C5 0.0371(14) 0.0513(16) 0.0338(13) -0.0084(12) 0.0065(11) 0.0077(12) C6 0.0370(13) 0.0404(14) 0.0276(11) -0.0031(10) 0.0016(9) 0.0033(11) C7 0.0315(12) 0.0385(13) 0.0370(13) 0.0012(11) -0.0004(10) -0.0014(10) C8 0.0306(12) 0.0399(14) 0.0369(13) 0.0003(11) -0.0002(10) -0.0022(10) C9 0.0289(11) 0.0353(12) 0.0314(11) 0.0005(10) 0.0005(9) -0.0083(10) C10 0.0285(12) 0.0418(14) 0.0472(15) -0.0033(12) 0.0035(10) -0.0037(11) C11 0.0466(16) 0.0444(15) 0.0432(15) -0.0101(13) 0.0158(12) -0.0103(13) C12 0.0528(16) 0.0416(14) 0.0288(12) 0.0011(11) 0.0012(11) -0.0200(13) C13 0.0399(14) 0.0426(15) 0.0366(13) 0.0061(11) -0.0069(11) -0.0069(12) C14 0.0349(13) 0.0408(14) 0.0320(12) -0.0006(10) 0.0011(10) 0.0001(11) C15A 0.039(6) 0.052(4) 0.034(4) 0.003(3) 0.009(5) -0.011(6) C15B 0.056(7) 0.055(5) 0.031(4) -0.003(3) 0.003(6) -0.022(7) 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' 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 120.8(2) . . ? C6 C1 I1 116.97(18) . . ? C2 C1 I1 122.21(17) . . ? C1 C2 C3 119.0(2) . . ? C1 C2 I2 122.68(17) . . ? C3 C2 I2 118.32(17) . . ? C4 C3 C2 119.4(2) . . ? C4 C3 C7 119.3(2) . . ? C2 C3 C7 121.3(2) . . ? C5 C4 C3 120.6(2) . . ? C4 C5 C6 120.0(2) . . ? C5 C6 C1 120.2(2) . . ? C8 C7 C3 179.2(3) . . ? C7 C8 C9 175.3(3) . . ? C10 C9 C14 119.4(2) . . ? C10 C9 C8 119.0(2) . . ? C14 C9 C8 121.5(2) . . ? C9 C10 C11 119.5(3) . . ? C10 C11 C12 120.3(3) . . ? C11 C12 C13 120.6(3) . . ? C11 C12 C15B 110.5(7) . . ? C13 C12 C15B 128.6(7) . . ? C11 C12 C15A 126.6(6) . . ? C13 C12 C15A 112.6(6) . . ? C14 C13 C12 119.3(3) . . ? C13 C14 C9 120.8(3) . . ? F1A C15A F3A 107.4(10) . . ? F1A C15A F2A 108.6(13) . . ? F3A C15A F2A 106.2(11) . . ? F1A C15A C12 117.8(11) . . ? F3A C15A C12 110.5(11) . . ? F2A C15A C12 105.8(8) . . ? F2B C15B F1B 107.6(14) . . ? F2B C15B F3B 105.8(10) . . ? F1B C15B F3B 106.6(13) . . ? F2B C15B C12 114.3(11) . . ? F1B C15B C12 107.5(9) . . ? F3B C15B C12 114.6(13) . . ? 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 C1 2.096(2) . ? I2 C2 2.093(2) . ? F1A C15A 1.299(15) . ? F2A C15A 1.357(12) . ? F3A C15A 1.328(17) . ? F1B C15B 1.317(14) . ? F2B C15B 1.311(15) . ? F3B C15B 1.344(18) . ? C1 C6 1.388(3) . ? C1 C2 1.394(3) . ? C2 C3 1.410(3) . ? C3 C4 1.401(4) . ? C3 C7 1.437(4) . ? C4 C5 1.383(4) . ? C5 C6 1.385(4) . ? C7 C8 1.190(4) . ? C8 C9 1.439(4) . ? C9 C10 1.397(4) . ? C9 C14 1.392(4) . ? C10 C11 1.394(4) . ? C11 C12 1.378(5) . ? C12 C13 1.386(4) . ? C12 C15B 1.497(15) . ? C12 C15A 1.554(16) . ? C13 C14 1.386(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 C6 C1 C2 C3 0.1(4) . . . . ? I1 C1 C2 C3 -178.90(17) . . . . ? C6 C1 C2 I2 179.39(19) . . . . ? I1 C1 C2 I2 0.4(3) . . . . ? C1 C2 C3 C4 0.6(4) . . . . ? I2 C2 C3 C4 -178.7(2) . . . . ? C1 C2 C3 C7 179.5(2) . . . . ? I2 C2 C3 C7 0.2(3) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C7 C3 C4 C5 -179.9(3) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C4 C5 C6 C1 0.2(5) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? I1 C1 C6 C5 178.5(2) . . . . ? C14 C9 C10 C11 1.4(4) . . . . ? C8 C9 C10 C11 -177.9(3) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C10 C11 C12 C13 -0.8(4) . . . . ? C10 C11 C12 C15B 173.5(7) . . . . ? C10 C11 C12 C15A -176.4(8) . . . . ? C11 C12 C13 C14 0.7(4) . . . . ? C15B C12 C13 C14 -172.5(8) . . . . ? C15A C12 C13 C14 176.9(7) . . . . ? C12 C13 C14 C9 0.5(4) . . . . ? C10 C9 C14 C13 -1.5(4) . . . . ? C8 C9 C14 C13 177.7(3) . . . . ? C11 C12 C15A F1A -169.6(8) . . . . ? C13 C12 C15A F1A 14.5(14) . . . . ? C11 C12 C15A F3A 66.5(10) . . . . ? C13 C12 C15A F3A -109.4(8) . . . . ? C11 C12 C15A F2A -48.1(14) . . . . ? C13 C12 C15A F2A 136.1(9) . . . . ? C11 C12 C15B F2B -82.7(14) . . . . ? C13 C12 C15B F2B 91.0(13) . . . . ? C11 C12 C15B F1B 157.9(10) . . . . ? C13 C12 C15B F1B -28.3(16) . . . . ? C11 C12 C15B F3B 39.7(11) . . . . ? C13 C12 C15B F3B -146.6(8) . . . . ?