#------------------------------------------------------------------------------ #$Date: 2023-10-24 03:13:16 +0300 (Tue, 24 Oct 2023) $ #$Revision: 287083 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247570.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_7247570 loop_ _publ_author_name 'Uchiyama, Hiromasa' 'Ban, Kazuho' 'Nozaki, Shiho' 'Ikeda, Yui' 'Ishimoto, Takayoshi' 'Fujioka, Hiroyoshi' 'Kamiya, Mako' 'Amari, Ryugo' 'Tsujino, Hirofumi' 'Arai, Masayoshi' 'Yamazoe, Sachi' 'Maekawa, Keiko' 'Kato, Takuma' 'Doi, Mitsunobu' 'Kadota, Kazunori' 'Tozuka, Yuichi' 'Tomita, Naohito' 'Sajiki, Hironao' 'Akai, Shuji' 'Sawama, Yoshinari' _publ_section_title ; Impact of multiple H/D replacements on the physicochemical properties of flurbiprofen ; _journal_name_full 'RSC Medicinal Chemistry' _journal_paper_doi 10.1039/D3MD00357D _journal_year 2023 _chemical_formula_moiety 'C15 H13 F O2' _chemical_formula_sum 'C15 H13 F O2' _chemical_formula_weight 244.25 _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 _audit_block_doi 10.5517/ccdc.csd.cc2gfvwn _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-06-28 deposited with the CCDC. 2023-10-09 downloaded from the CCDC. ; _cell_angle_alpha 73.094(3) _cell_angle_beta 82.925(3) _cell_angle_gamma 72.866(3) _cell_formula_units_Z 2 _cell_length_a 5.7122(2) _cell_length_b 9.2022(3) _cell_length_c 12.6766(4) _cell_measurement_reflns_used 7947 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 70.4900 _cell_measurement_theta_min 3.6470 _cell_volume 608.74(4) _computing_cell_refinement 'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-2014/6 (Sheldrick, 2014)' _diffrn_ambient_temperature 93(2) _diffrn_detector_area_resol_mean 5.8140 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_unetI/netI 0.0153 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9695 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.917 _diffrn_reflns_theta_min 3.647 _diffrn_source 'Rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 0.809 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.333 _exptl_crystal_description plate _exptl_crystal_F_000 256 _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.068 _refine_diff_density_max 0.631 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2284 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0481 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0693P)^2^+0.3593P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1282 _refine_ls_wR_factor_ref 0.1288 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2208 _reflns_number_total 2284 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3md00357d2.cif _cod_data_source_block Me60 _cod_database_code 7247570 _shelx_shelxl_version_number 2018/3 _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_res_file ; TITL 20221007_Me60_auto in P-1 Me60.res created by SHELXL-2018/3 at 14:47:14 on 07-Oct-2022 CELL 1.54184 5.7122 9.2022 12.6766 73.094 82.925 72.866 ZERR 2.00 0.0002 0.0003 0.0004 0.003 0.003 0.003 LATT 1 SFAC C H O F UNIT 30 26 4 2 MERG 2 FMAP 2 PLAN 20 HTAB BOND $H CONF ACTA L.S. 40 TEMP -180.00 WGHT 0.069300 0.359300 FVAR 15.07842 MOLE 1 C1 1 0.006737 0.799583 0.102160 11.00000 0.03307 0.02419 = 0.01848 -0.00639 -0.00118 -0.00915 C2 1 0.011042 0.645703 0.189213 11.00000 0.03444 0.02198 = 0.02335 -0.00427 -0.00005 -0.00915 AFIX 13 H2 2 0.179892 0.572653 0.189283 11.00000 -1.20000 AFIX 0 C3 1 -0.169761 0.567624 0.163749 11.00000 0.04483 0.02721 = 0.02858 -0.00564 -0.00357 -0.01562 AFIX 137 H3A 2 -0.334881 0.640416 0.159373 11.00000 -1.50000 H3B 2 -0.169158 0.470832 0.222448 11.00000 -1.50000 H3C 2 -0.121043 0.541617 0.093118 11.00000 -1.50000 AFIX 0 O1 3 0.224209 0.818420 0.068471 11.00000 0.03346 0.03114 = 0.03613 0.00321 0.00261 -0.01214 AFIX 83 H1 2 0.209878 0.905282 0.020584 11.00000 -1.50000 AFIX 0 O2 3 -0.183081 0.898014 0.069376 11.00000 0.03407 0.03195 = 0.02562 -0.00091 0.00140 -0.01506 C11 1 -0.044215 0.684701 0.300492 11.00000 0.03212 0.01679 = 0.02224 -0.00189 0.00243 -0.01208 C12 1 0.140796 0.639184 0.374188 11.00000 0.02610 0.01724 = 0.02562 -0.00308 0.00292 -0.00880 AFIX 43 H12 2 0.301821 0.582729 0.356364 11.00000 -1.20000 AFIX 0 C13 1 0.088371 0.676814 0.473681 11.00000 0.02557 0.01739 = 0.02415 -0.00160 -0.00142 -0.01004 C14 1 -0.141475 0.759842 0.505472 11.00000 0.02572 0.01652 = 0.02218 -0.00234 0.00003 -0.01028 C15 1 -0.324844 0.805468 0.429579 11.00000 0.02525 0.02004 = 0.02445 -0.00362 -0.00055 -0.00750 AFIX 43 H15 2 -0.485272 0.862991 0.447215 11.00000 -1.20000 AFIX 0 C16 1 -0.277595 0.768496 0.328774 11.00000 0.03118 0.02416 = 0.02198 -0.00043 -0.00446 -0.01232 AFIX 43 H16 2 -0.405759 0.800727 0.278787 11.00000 -1.20000 AFIX 0 F13 4 0.271238 0.624945 0.545817 11.00000 0.02713 0.03071 = 0.03102 -0.00786 -0.00499 -0.00629 C21 1 -0.192019 0.795587 0.614490 11.00000 0.02436 0.01632 = 0.02331 -0.00400 -0.00312 -0.00414 C22 1 -0.049236 0.871416 0.649797 11.00000 0.02833 0.02095 = 0.02954 -0.00650 -0.00303 -0.00770 AFIX 43 H22 2 0.083642 0.899848 0.603927 11.00000 -1.20000 AFIX 0 C23 1 -0.100260 0.905356 0.751219 11.00000 0.03529 0.02758 = 0.03781 -0.01478 -0.00917 -0.00695 AFIX 43 H23 2 -0.004134 0.958590 0.773826 11.00000 -1.20000 AFIX 0 C24 1 -0.291204 0.861887 0.819878 11.00000 0.03814 0.03684 = 0.02806 -0.01665 -0.00458 -0.00313 AFIX 43 H24 2 -0.324123 0.883601 0.889874 11.00000 -1.20000 AFIX 0 C25 1 -0.433701 0.786522 0.785644 11.00000 0.03049 0.03608 = 0.02762 -0.01055 0.00204 -0.00810 AFIX 43 H25 2 -0.564339 0.756407 0.832416 11.00000 -1.20000 AFIX 0 C26 1 -0.385915 0.754964 0.683166 11.00000 0.02589 0.02422 = 0.02564 -0.00758 -0.00139 -0.00755 AFIX 43 H26 2 -0.486362 0.705246 0.659732 11.00000 -1.20000 AFIX 0 HKLF 4 REM 20221007_Me60_auto in P-1 REM wR2 = 0.1288, GooF = S = 1.046, Restrained GooF = 1.046 for all data REM R1 = 0.0481 for 2208 Fo > 4sig(Fo) and 0.0489 for all 2284 data REM 164 parameters refined using 0 restraints END WGHT 0.0694 0.3574 REM Instructions for potential hydrogen bonds EQIV $1 -x, -y+2, -z HTAB O1 O2_$1 REM Highest difference peak 0.631, deepest hole -0.305, 1-sigma level 0.061 Q1 1 -0.5416 0.8774 0.4587 11.00000 0.05 0.63 Q2 1 0.0502 0.5444 0.1595 11.00000 0.05 0.34 Q3 1 -0.1586 0.6814 0.1749 11.00000 0.05 0.31 Q4 1 -0.3023 0.9865 0.0596 11.00000 0.05 0.25 Q5 1 -0.0971 1.0620 0.7241 11.00000 0.05 0.15 Q6 1 0.2394 0.5790 0.6572 11.00000 0.05 0.15 Q7 1 -0.5031 0.9829 0.4634 11.00000 0.05 0.14 Q8 1 -0.1872 0.8048 0.5598 11.00000 0.05 0.14 Q9 1 -0.2664 0.7573 0.6556 11.00000 0.05 0.14 Q10 1 -0.3790 0.5465 0.7248 11.00000 0.05 0.13 Q11 1 -0.0176 0.9964 0.5406 11.00000 0.05 0.13 Q12 1 -0.5807 0.9423 0.6226 11.00000 0.05 0.13 Q13 1 -0.5916 0.9398 0.5385 11.00000 0.05 0.13 Q14 1 0.4287 0.5456 0.6280 11.00000 0.05 0.13 Q15 1 -0.4718 0.9761 0.8557 11.00000 0.05 0.13 Q16 1 0.1991 0.9737 0.5390 11.00000 0.05 0.13 Q17 1 0.2937 0.4747 0.5862 11.00000 0.05 0.13 Q18 1 0.4845 0.5194 0.5536 11.00000 0.05 0.13 Q19 1 0.3132 0.9626 0.7430 11.00000 0.05 0.13 Q20 1 -0.0612 1.0195 0.5240 11.00000 0.05 0.12 ; _shelx_res_checksum 45288 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 C1 C 0.0067(3) 0.79958(18) 0.10216(12) 0.0248(4) Uani 1 1 d . . . . . C2 C 0.0110(3) 0.64570(19) 0.18921(13) 0.0268(4) Uani 1 1 d . . . . . H2 H 0.179892 0.572653 0.189283 0.032 Uiso 1 1 calc R U . . . C3 C -0.1698(3) 0.5676(2) 0.16375(14) 0.0325(4) Uani 1 1 d . . . . . H3A H -0.334881 0.640416 0.159373 0.049 Uiso 1 1 calc R U . . . H3B H -0.169158 0.470832 0.222448 0.049 Uiso 1 1 calc R U . . . H3C H -0.121043 0.541617 0.093118 0.049 Uiso 1 1 calc R U . . . O1 O 0.2242(2) 0.81842(14) 0.06847(10) 0.0359(3) Uani 1 1 d . . . . . H1 H 0.209878 0.905282 0.020584 0.054 Uiso 1 1 calc R U . . . O2 O -0.1831(2) 0.89801(14) 0.06938(9) 0.0309(3) Uani 1 1 d . . . . . C11 C -0.0442(3) 0.68470(17) 0.30049(12) 0.0236(3) Uani 1 1 d . . . . . C12 C 0.1408(3) 0.63918(17) 0.37419(12) 0.0233(3) Uani 1 1 d . . . . . H12 H 0.301821 0.582729 0.356364 0.028 Uiso 1 1 calc R U . . . C13 C 0.0884(3) 0.67681(17) 0.47368(12) 0.0223(3) Uani 1 1 d . . . . . C14 C -0.1415(3) 0.75984(17) 0.50547(12) 0.0212(3) Uani 1 1 d . . . . . C15 C -0.3248(3) 0.80547(18) 0.42958(12) 0.0235(3) Uani 1 1 d . . . . . H15 H -0.485272 0.862991 0.447215 0.028 Uiso 1 1 calc R U . . . C16 C -0.2776(3) 0.76850(18) 0.32877(13) 0.0257(4) Uani 1 1 d . . . . . H16 H -0.405759 0.800727 0.278787 0.031 Uiso 1 1 calc R U . . . F13 F 0.27124(17) 0.62494(11) 0.54582(8) 0.0297(3) Uani 1 1 d . . . . . C21 C -0.1920(3) 0.79559(17) 0.61449(12) 0.0217(3) Uani 1 1 d . . . . . C22 C -0.0492(3) 0.87142(18) 0.64980(13) 0.0259(4) Uani 1 1 d . . . . . H22 H 0.083642 0.899848 0.603927 0.031 Uiso 1 1 calc R U . . . C23 C -0.1003(3) 0.9054(2) 0.75122(15) 0.0319(4) Uani 1 1 d . . . . . H23 H -0.004134 0.958590 0.773826 0.038 Uiso 1 1 calc R U . . . C24 C -0.2912(3) 0.8619(2) 0.81988(14) 0.0339(4) Uani 1 1 d . . . . . H24 H -0.324123 0.883601 0.889874 0.041 Uiso 1 1 calc R U . . . C25 C -0.4337(3) 0.7865(2) 0.78564(14) 0.0315(4) Uani 1 1 d . . . . . H25 H -0.564339 0.756407 0.832416 0.038 Uiso 1 1 calc R U . . . C26 C -0.3859(3) 0.75496(18) 0.68317(13) 0.0249(3) Uani 1 1 d . . . . . H26 H -0.486362 0.705246 0.659732 0.030 Uiso 1 1 calc R U . . . 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 0.0331(9) 0.0242(8) 0.0185(7) -0.0064(6) -0.0012(6) -0.0092(7) C2 0.0344(9) 0.0220(8) 0.0234(8) -0.0043(6) 0.0000(6) -0.0091(7) C3 0.0448(10) 0.0272(8) 0.0286(8) -0.0056(7) -0.0036(7) -0.0156(8) O1 0.0335(7) 0.0311(7) 0.0361(7) 0.0032(5) 0.0026(5) -0.0121(5) O2 0.0341(7) 0.0319(6) 0.0256(6) -0.0009(5) 0.0014(5) -0.0151(5) C11 0.0321(9) 0.0168(7) 0.0222(7) -0.0019(6) 0.0024(6) -0.0121(6) C12 0.0261(8) 0.0172(7) 0.0256(8) -0.0031(6) 0.0029(6) -0.0088(6) C13 0.0256(8) 0.0174(7) 0.0241(7) -0.0016(6) -0.0014(6) -0.0100(6) C14 0.0257(8) 0.0165(7) 0.0222(7) -0.0023(5) 0.0000(6) -0.0103(6) C15 0.0252(8) 0.0200(7) 0.0244(8) -0.0036(6) -0.0005(6) -0.0075(6) C16 0.0312(9) 0.0242(8) 0.0220(7) -0.0004(6) -0.0045(6) -0.0123(7) F13 0.0271(5) 0.0307(5) 0.0310(5) -0.0079(4) -0.0050(4) -0.0063(4) C21 0.0244(8) 0.0163(7) 0.0233(7) -0.0040(6) -0.0031(6) -0.0041(6) C22 0.0283(8) 0.0209(7) 0.0295(8) -0.0065(6) -0.0030(6) -0.0077(6) C23 0.0353(9) 0.0276(8) 0.0378(9) -0.0148(7) -0.0092(7) -0.0069(7) C24 0.0381(10) 0.0368(9) 0.0281(8) -0.0167(7) -0.0046(7) -0.0031(8) C25 0.0305(9) 0.0361(9) 0.0276(8) -0.0105(7) 0.0020(7) -0.0081(7) C26 0.0259(8) 0.0242(8) 0.0256(8) -0.0076(6) -0.0014(6) -0.0076(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 '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 O2 C1 O1 123.41(14) . . ? O2 C1 C2 122.63(15) . . ? O1 C1 C2 113.93(14) . . ? C1 C2 C11 106.81(12) . . ? C1 C2 C3 110.75(13) . . ? C11 C2 C3 113.29(13) . . ? C1 C2 H2 108.6 . . ? C11 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 O1 H1 109.5 . . ? C12 C11 C16 118.94(14) . . ? C12 C11 C2 119.96(14) . . ? C16 C11 C2 121.09(14) . . ? C13 C12 C11 119.20(14) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? F13 C13 C12 117.69(14) . . ? F13 C13 C14 118.41(13) . . ? C12 C13 C14 123.87(14) . . ? C13 C14 C15 115.95(14) . . ? C13 C14 C21 122.29(13) . . ? C15 C14 C21 121.75(14) . . ? C16 C15 C14 121.44(15) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C11 120.60(14) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C26 C21 C22 118.73(14) . . ? C26 C21 C14 120.06(13) . . ? C22 C21 C14 121.20(14) . . ? C23 C22 C21 120.51(15) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 120.30(15) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 119.61(15) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.22(16) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 120.60(15) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? 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 O2 1.217(2) . ? C1 O1 1.307(2) . ? C1 C2 1.517(2) . ? C2 C11 1.528(2) . ? C2 C3 1.530(2) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? O1 H1 0.8400 . ? C11 C12 1.386(2) . ? C11 C16 1.392(2) . ? C12 C13 1.378(2) . ? C12 H12 0.9500 . ? C13 F13 1.3575(18) . ? C13 C14 1.388(2) . ? C14 C15 1.398(2) . ? C14 C21 1.487(2) . ? C15 C16 1.391(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.393(2) . ? C21 C22 1.400(2) . ? C22 C23 1.387(2) . ? C22 H22 0.9500 . ? C23 C24 1.388(3) . ? C23 H23 0.9500 . ? C24 C25 1.388(3) . ? C24 H24 0.9500 . ? C25 C26 1.390(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 O2 C1 C2 C11 -77.35(18) . . . . ? O1 C1 C2 C11 100.67(15) . . . . ? O2 C1 C2 C3 46.4(2) . . . . ? O1 C1 C2 C3 -135.53(15) . . . . ? C1 C2 C11 C12 -107.70(15) . . . . ? C3 C2 C11 C12 130.09(15) . . . . ? C1 C2 C11 C16 71.02(18) . . . . ? C3 C2 C11 C16 -51.20(19) . . . . ? C16 C11 C12 C13 0.6(2) . . . . ? C2 C11 C12 C13 179.30(13) . . . . ? C11 C12 C13 F13 177.39(12) . . . . ? C11 C12 C13 C14 -0.5(2) . . . . ? F13 C13 C14 C15 -177.80(12) . . . . ? C12 C13 C14 C15 0.0(2) . . . . ? F13 C13 C14 C21 1.0(2) . . . . ? C12 C13 C14 C21 178.82(13) . . . . ? C13 C14 C15 C16 0.3(2) . . . . ? C21 C14 C15 C16 -178.51(13) . . . . ? C14 C15 C16 C11 -0.2(2) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C2 C11 C16 C15 -178.99(13) . . . . ? C13 C14 C21 C26 -126.95(16) . . . . ? C15 C14 C21 C26 51.8(2) . . . . ? C13 C14 C21 C22 53.7(2) . . . . ? C15 C14 C21 C22 -127.59(16) . . . . ? C26 C21 C22 C23 0.0(2) . . . . ? C14 C21 C22 C23 179.35(14) . . . . ? C21 C22 C23 C24 1.2(2) . . . . ? C22 C23 C24 C25 -1.1(3) . . . . ? C23 C24 C25 C26 -0.1(3) . . . . ? C24 C25 C26 C21 1.3(2) . . . . ? C22 C21 C26 C25 -1.2(2) . . . . ? C14 C21 C26 C25 179.44(14) . . . . ?