#------------------------------------------------------------------------------ #$Date: 2020-04-25 04:19:33 +0300 (Sat, 25 Apr 2020) $ #$Revision: 251173 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240400.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_7240400 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_paper_doi 10.1039/D0RA01569E _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C15 H6 Cl F3 I2' _chemical_formula_sum 'C15 H6 Cl F3 I2' _chemical_formula_weight 532.45 _chemical_name_systematic ; 5-chloro-1,2-diiodo-3-{[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 72.6614(8) _cell_angle_beta 71.6046(7) _cell_angle_gamma 64.6041(7) _cell_formula_units_Z 2 _cell_length_a 8.4281(5) _cell_length_b 9.5746(5) _cell_length_c 11.4227(6) _cell_measurement_reflns_used 9944 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 30.57 _cell_measurement_theta_min 2.40 _cell_volume 775.78(7) _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 173(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0091 _diffrn_reflns_av_unetI/netI 0.0133 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9508 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.631 _diffrn_reflns_theta_min 1.914 _exptl_absorpt_coefficient_mu 4.246 _exptl_absorpt_correction_T_max 0.4694 _exptl_absorpt_correction_T_min 0.3060 _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 2.279 _exptl_crystal_description fragment _exptl_crystal_F_000 492 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: hexanes/dichloromethane' _exptl_crystal_size_max 0.215 _exptl_crystal_size_mid 0.181 _exptl_crystal_size_min 0.071 _refine_diff_density_max 1.103 _refine_diff_density_min -0.604 _refine_diff_density_rms 0.071 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 4763 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0180 _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^)+(0.0165P)^2^+0.6203P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0426 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4325 _reflns_number_total 4763 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra01569e2.cif _cod_data_source_block jus1810 _cod_database_code 7240400 _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 0.462 _shelx_estimated_absorpt_t_max 0.753 _shelx_res_file ; TITL jus1810 in P-1 jus1810.res created by SHELXL-2017/1 at 09:43:15 on 03-Dec-2018 CELL 0.71073 8.42810 9.57460 11.42270 72.6614 71.6046 64.6041 ZERR 2.00 0.00050 0.00050 0.00060 0.0008 0.0007 0.0007 LATT 1 SFAC C H F CL I UNIT 30 12 6 2 4 TEMP -100.000 SIZE 0.071 0.181 0.215 L.S. 4 ACTA CONF WGHT 0.016500 0.620300 FVAR 0.11990 0.91172 I1 5 0.449082 0.085271 0.147136 11.00000 0.03946 0.04242 = 0.03313 -0.01448 -0.01690 -0.00749 I2 5 0.257240 0.371218 0.353740 11.00000 0.02610 0.02719 = 0.04124 -0.01034 -0.01030 0.00095 CL1 4 1.057472 -0.193023 0.363305 11.00000 0.02440 0.03703 = 0.04264 -0.02023 -0.00876 0.00449 PART 1 F1A 3 0.179146 0.769765 1.030124 21.00000 0.06942 0.09273 = 0.07759 -0.06663 0.00631 -0.03726 F2A 3 -0.012093 0.662893 1.094642 21.00000 0.11849 0.07095 = 0.05455 -0.04278 0.05334 -0.06049 F3A 3 -0.048643 0.871185 0.950651 21.00000 0.07731 0.05835 = 0.07946 -0.05143 -0.02573 0.02304 PART 2 F1B 3 0.137310 0.695159 1.083670 -21.00000 0.05495 F2B 3 -0.095979 0.724618 1.039773 -21.00000 0.03403 F3B 3 0.030258 0.868544 0.956894 -21.00000 0.03196 PART 0 C1 1 0.579923 0.079077 0.277879 11.00000 0.02618 0.02416 = 0.02137 -0.00686 -0.00586 -0.00756 C2 1 0.502696 0.182854 0.362002 11.00000 0.02004 0.01962 = 0.02292 -0.00607 -0.00331 -0.00463 C3 1 0.594589 0.162388 0.453132 11.00000 0.02305 0.02012 = 0.02201 -0.00837 -0.00134 -0.00746 C4 1 0.764136 0.042670 0.455406 11.00000 0.02304 0.02563 = 0.02463 -0.00993 -0.00493 -0.00611 AFIX 43 H4 2 0.825829 0.026761 0.517786 11.00000 -1.20000 AFIX 0 C5 1 0.841370 -0.052302 0.366431 11.00000 0.02064 0.02244 = 0.02691 -0.00977 -0.00367 -0.00238 C6 1 0.750218 -0.038278 0.279069 11.00000 0.02655 0.02522 = 0.02469 -0.01191 -0.00281 -0.00531 AFIX 43 H6 2 0.802955 -0.107557 0.220897 11.00000 -1.20000 AFIX 0 C7 1 0.517064 0.261155 0.545095 11.00000 0.02339 0.02419 = 0.02550 -0.00814 -0.00263 -0.00693 C8 1 0.451446 0.340734 0.623783 11.00000 0.02445 0.02560 = 0.02546 -0.00933 -0.00243 -0.00793 C9 1 0.358673 0.439643 0.716343 11.00000 0.02406 0.02444 = 0.02332 -0.01022 -0.00035 -0.00853 C10 1 0.205040 0.572028 0.696268 11.00000 0.02620 0.03009 = 0.02331 -0.00975 -0.00362 -0.00667 AFIX 43 H10 2 0.164151 0.596713 0.621359 11.00000 -1.20000 AFIX 0 C11 1 0.111319 0.668144 0.785309 11.00000 0.02567 0.02543 = 0.03037 -0.01046 -0.00122 -0.00385 AFIX 43 H11 2 0.006301 0.758089 0.771689 11.00000 -1.20000 AFIX 0 C12 1 0.172158 0.631807 0.893899 11.00000 0.03084 0.02746 = 0.02686 -0.01441 0.00372 -0.01239 C13 1 0.324362 0.500008 0.915474 11.00000 0.03909 0.03743 = 0.02787 -0.01544 -0.00964 -0.00779 AFIX 43 H13 2 0.364075 0.475653 0.990826 11.00000 -1.20000 AFIX 0 C14 1 0.418528 0.403785 0.826807 11.00000 0.03137 0.02975 = 0.03216 -0.01420 -0.00989 -0.00111 AFIX 43 H14 2 0.523292 0.313854 0.841038 11.00000 -1.20000 AFIX 0 C15 1 0.071810 0.733175 0.991846 11.00000 0.04401 0.03612 = 0.03489 -0.02081 0.00547 -0.01622 HKLF 4 REM jus1810 in P-1 REM R1 = 0.0180 for 4325 Fo > 4sig(Fo) and 0.0207 for all 4763 data REM 203 parameters refined using 0 restraints END WGHT 0.0165 0.6203 REM Highest difference peak 1.103, deepest hole -0.604, 1-sigma level 0.071 Q1 1 0.4598 0.1631 0.1263 11.00000 0.05 1.10 Q2 1 -0.1138 0.7994 0.9995 11.00000 0.05 0.58 Q3 1 0.2576 0.2842 0.3717 11.00000 0.05 0.44 Q4 1 0.6808 0.1046 0.4558 11.00000 0.05 0.40 Q5 1 0.5472 0.1801 0.4095 11.00000 0.05 0.37 Q6 1 0.0182 0.6046 1.1086 11.00000 0.05 0.37 Q7 1 0.0800 0.6608 1.0990 11.00000 0.05 0.36 Q8 1 0.1364 0.6758 0.9391 11.00000 0.05 0.36 Q9 1 0.5413 0.1391 0.3139 11.00000 0.05 0.35 Q10 1 0.1000 0.8552 0.9662 11.00000 0.05 0.34 Q11 1 0.6608 0.0208 0.2780 11.00000 0.05 0.34 Q12 1 0.2356 0.5592 0.9000 11.00000 0.05 0.34 Q13 1 0.8076 0.0002 0.4072 11.00000 0.05 0.33 Q14 1 0.2965 0.5060 0.7012 11.00000 0.05 0.33 Q15 1 0.4229 -0.0240 0.1794 11.00000 0.05 0.32 Q16 1 0.3621 0.4467 0.8806 11.00000 0.05 0.32 Q17 1 0.7982 -0.0567 0.3292 11.00000 0.05 0.31 Q18 1 0.1418 0.6440 0.8434 11.00000 0.05 0.31 Q19 1 0.1756 0.6222 0.7396 11.00000 0.05 0.31 Q20 1 -0.0601 0.9025 0.9048 11.00000 0.05 0.30 ; _shelx_res_checksum 43488 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 0.44908(2) 0.08527(2) 0.14714(2) 0.03707(4) Uani 1 1 d . . . . . I2 I 0.25724(2) 0.37122(2) 0.35374(2) 0.03377(4) Uani 1 1 d . . . . . Cl1 Cl 1.05747(6) -0.19302(6) 0.36331(5) 0.03706(11) Uani 1 1 d . . . . . F1A F 0.1791(3) 0.7698(3) 1.0301(2) 0.0708(8) Uani 0.912(5) 1 d . . P A 1 F2A F -0.0121(4) 0.6629(3) 1.0946(2) 0.0831(11) Uani 0.912(5) 1 d . . P A 1 F3A F -0.0486(4) 0.8712(2) 0.9507(2) 0.0779(8) Uani 0.912(5) 1 d . . P A 1 F1B F 0.137(3) 0.695(2) 1.0837(19) 0.055(5) Uiso 0.088(5) 1 d . . P A 2 F2B F -0.096(2) 0.7246(18) 1.0398(15) 0.034(4) Uiso 0.088(5) 1 d . . P A 2 F3B F 0.030(2) 0.8685(19) 0.9569(15) 0.032(4) Uiso 0.088(5) 1 d . . P A 2 C1 C 0.5799(2) 0.07908(19) 0.27788(15) 0.0238(3) Uani 1 1 d . . . . . C2 C 0.5027(2) 0.18285(18) 0.36200(15) 0.0217(3) Uani 1 1 d . . . . . C3 C 0.5946(2) 0.16239(18) 0.45313(15) 0.0218(3) Uani 1 1 d . . . . . C4 C 0.7641(2) 0.0427(2) 0.45541(16) 0.0243(3) Uani 1 1 d . . . . . H4 H 0.825829 0.026761 0.517786 0.029 Uiso 1 1 calc R U . . . C5 C 0.8414(2) -0.05230(19) 0.36643(16) 0.0245(3) Uani 1 1 d . . . . . C6 C 0.7502(2) -0.0383(2) 0.27907(16) 0.0260(3) Uani 1 1 d . . . . . H6 H 0.802955 -0.107557 0.220897 0.031 Uiso 1 1 calc R U . . . C7 C 0.5171(2) 0.2612(2) 0.54510(16) 0.0249(3) Uani 1 1 d . . . . . C8 C 0.4514(2) 0.3407(2) 0.62378(16) 0.0253(3) Uani 1 1 d . . . . . C9 C 0.3587(2) 0.4396(2) 0.71634(16) 0.0240(3) Uani 1 1 d . . . . . C10 C 0.2050(2) 0.5720(2) 0.69627(16) 0.0272(3) Uani 1 1 d . . . . . H10 H 0.164151 0.596713 0.621359 0.033 Uiso 1 1 calc R U . . . C11 C 0.1113(2) 0.6681(2) 0.78531(17) 0.0292(4) Uani 1 1 d . . . . . H11 H 0.006301 0.758089 0.771689 0.035 Uiso 1 1 calc R U . . . C12 C 0.1722(3) 0.6318(2) 0.89390(17) 0.0281(3) Uani 1 1 d . . . . . C13 C 0.3244(3) 0.5000(2) 0.91547(18) 0.0343(4) Uani 1 1 d . . . . . H13 H 0.364075 0.475653 0.990826 0.041 Uiso 1 1 calc R U . . . C14 C 0.4185(3) 0.4038(2) 0.82681(18) 0.0320(4) Uani 1 1 d . . . . . H14 H 0.523292 0.313854 0.841038 0.038 Uiso 1 1 calc R U . . . C15 C 0.0718(3) 0.7332(3) 0.9918(2) 0.0380(4) 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 0.03946(7) 0.04242(7) 0.03313(7) -0.01448(5) -0.01690(5) -0.00749(6) I2 0.02610(6) 0.02719(6) 0.04124(7) -0.01034(5) -0.01030(5) 0.00095(4) Cl1 0.0244(2) 0.0370(2) 0.0426(3) -0.0202(2) -0.00876(18) 0.00449(17) F1A 0.0694(12) 0.0927(16) 0.0776(15) -0.0666(13) 0.0063(10) -0.0373(11) F2A 0.118(2) 0.0710(14) 0.0545(13) -0.0428(11) 0.0533(14) -0.0605(16) F3A 0.0773(17) 0.0584(11) 0.0795(14) -0.0514(11) -0.0257(12) 0.0230(11) C1 0.0262(8) 0.0242(7) 0.0214(7) -0.0069(6) -0.0059(6) -0.0076(6) C2 0.0200(7) 0.0196(7) 0.0229(7) -0.0061(5) -0.0033(6) -0.0046(6) C3 0.0230(7) 0.0201(7) 0.0220(7) -0.0084(6) -0.0013(6) -0.0075(6) C4 0.0230(8) 0.0256(8) 0.0246(8) -0.0099(6) -0.0049(6) -0.0061(6) C5 0.0206(7) 0.0224(7) 0.0269(8) -0.0098(6) -0.0037(6) -0.0024(6) C6 0.0265(8) 0.0252(8) 0.0247(8) -0.0119(6) -0.0028(6) -0.0053(6) C7 0.0234(8) 0.0242(7) 0.0255(8) -0.0081(6) -0.0026(6) -0.0069(6) C8 0.0244(8) 0.0256(8) 0.0255(8) -0.0093(6) -0.0024(6) -0.0079(6) C9 0.0241(8) 0.0244(7) 0.0233(7) -0.0102(6) -0.0003(6) -0.0085(6) C10 0.0262(8) 0.0301(8) 0.0233(8) -0.0098(6) -0.0036(6) -0.0067(7) C11 0.0257(8) 0.0254(8) 0.0304(9) -0.0105(7) -0.0012(7) -0.0038(7) C12 0.0308(9) 0.0275(8) 0.0269(8) -0.0144(7) 0.0037(7) -0.0124(7) C13 0.0391(10) 0.0374(10) 0.0279(9) -0.0154(7) -0.0096(8) -0.0078(8) C14 0.0314(9) 0.0297(9) 0.0322(9) -0.0142(7) -0.0099(7) -0.0011(7) C15 0.0440(11) 0.0361(10) 0.0349(10) -0.0208(8) 0.0055(8) -0.0162(9) 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 120.80(15) . . ? C6 C1 I1 116.08(12) . . ? C2 C1 I1 123.10(12) . . ? C1 C2 C3 119.20(15) . . ? C1 C2 I2 121.91(12) . . ? C3 C2 I2 118.87(11) . . ? C4 C3 C2 119.74(14) . . ? C4 C3 C7 119.03(15) . . ? C2 C3 C7 121.23(15) . . ? C5 C4 C3 119.64(16) . . ? C4 C5 C6 121.50(16) . . ? C4 C5 Cl1 119.64(13) . . ? C6 C5 Cl1 118.86(13) . . ? C5 C6 C1 118.95(15) . . ? C8 C7 C3 178.48(19) . . ? C7 C8 C9 175.39(19) . . ? C10 C9 C14 119.64(15) . . ? C10 C9 C8 119.25(16) . . ? C14 C9 C8 121.10(16) . . ? C11 C10 C9 120.33(17) . . ? C12 C11 C10 119.49(17) . . ? C11 C12 C13 120.83(16) . . ? C11 C12 C15 120.32(18) . . ? C13 C12 C15 118.83(18) . . ? C12 C13 C14 119.90(17) . . ? C13 C14 C9 119.80(17) . . ? F3B C15 F1B 108.8(12) . . ? F2A C15 F1A 105.2(2) . . ? F2A C15 F3A 108.1(2) . . ? F1A C15 F3A 104.9(2) . . ? F3B C15 F2B 99.5(10) . . ? F1B C15 F2B 104.9(12) . . ? F3B C15 C12 116.9(8) . . ? F1B C15 C12 116.2(9) . . ? F2A C15 C12 112.55(17) . . ? F1A C15 C12 112.51(18) . . ? F3A C15 C12 113.06(19) . . ? F2B C15 C12 108.5(6) . . ? 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 2.0930(17) . ? I2 C2 2.0887(16) . ? Cl1 C5 1.7368(17) . ? F1A C15 1.321(3) . ? F2A C15 1.321(3) . ? F3A C15 1.334(3) . ? F1B C15 1.226(19) . ? F2B C15 1.375(15) . ? F3B C15 1.163(16) . ? C1 C6 1.394(2) . ? C1 C2 1.398(2) . ? C2 C3 1.407(2) . ? C3 C4 1.399(2) . ? C3 C7 1.433(2) . ? C4 C5 1.382(2) . ? C5 C6 1.385(2) . ? C7 C8 1.195(2) . ? C8 C9 1.437(2) . ? C9 C10 1.394(2) . ? C9 C14 1.400(3) . ? C10 C11 1.390(2) . ? C11 C12 1.383(3) . ? C12 C13 1.387(3) . ? C12 C15 1.502(2) . ? C13 C14 1.388(2) . ? 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 -3.5(3) . . . . ? I1 C1 C2 C3 175.11(12) . . . . ? C6 C1 C2 I2 175.00(13) . . . . ? I1 C1 C2 I2 -6.4(2) . . . . ? C1 C2 C3 C4 2.3(2) . . . . ? I2 C2 C3 C4 -176.20(12) . . . . ? C1 C2 C3 C7 -177.05(16) . . . . ? I2 C2 C3 C7 4.4(2) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? C7 C3 C4 C5 -179.28(16) . . . . ? C3 C4 C5 C6 -4.0(3) . . . . ? C3 C4 C5 Cl1 176.10(13) . . . . ? C4 C5 C6 C1 2.8(3) . . . . ? Cl1 C5 C6 C1 -177.24(14) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? I1 C1 C6 C5 -177.74(13) . . . . ? C14 C9 C10 C11 -0.1(3) . . . . ? C8 C9 C10 C11 178.98(17) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? C10 C11 C12 C15 -179.38(18) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C15 C12 C13 C14 179.47(19) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? C10 C9 C14 C13 0.1(3) . . . . ? C8 C9 C14 C13 -178.88(19) . . . . ? C11 C12 C15 F3B -47.4(10) . . . . ? C13 C12 C15 F3B 133.8(10) . . . . ? C11 C12 C15 F1B -178.2(13) . . . . ? C13 C12 C15 F1B 3.0(13) . . . . ? C11 C12 C15 F2A 109.0(3) . . . . ? C13 C12 C15 F2A -69.8(3) . . . . ? C11 C12 C15 F1A -132.4(2) . . . . ? C13 C12 C15 F1A 48.8(3) . . . . ? C11 C12 C15 F3A -13.8(3) . . . . ? C13 C12 C15 F3A 167.4(2) . . . . ? C11 C12 C15 F2B 64.0(8) . . . . ? C13 C12 C15 F2B -114.8(8) . . . . ?