#------------------------------------------------------------------------------ #$Date: 2023-10-24 03:13:16 +0300 (Tue, 24 Oct 2023) $ #$Revision: 287083 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247571.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_7247571 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 H5 D8 F O2' _chemical_formula_sum 'C15 H5 D8 F O2' _chemical_formula_weight 252.30 _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.cc2gfvxp _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 73.270(3) _cell_angle_beta 82.917(3) _cell_angle_gamma 72.913(3) _cell_formula_units_Z 2 _cell_length_a 5.7120(2) _cell_length_b 9.1610(3) _cell_length_c 12.6671(5) _cell_measurement_reflns_used 8692 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 70.3290 _cell_measurement_theta_min 3.6700 _cell_volume 606.22(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 0.986 _diffrn_measured_fraction_theta_max 0.974 _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 0.0227 _diffrn_reflns_av_unetI/netI 0.0127 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.974 _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 10225 _diffrn_reflns_point_group_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.660 _diffrn_reflns_theta_min 3.647 _diffrn_source 'Rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 0.813 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.42090 _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 1.382 _exptl_crystal_description needle _exptl_crystal_F_000 256 _exptl_crystal_size_max 0.505 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.146 _refine_diff_density_max 0.525 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.059 _refine_ls_extinction_coef 0.015(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 2265 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0544 _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^)+(0.0834P)^2^+0.4906P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1539 _refine_ls_wR_factor_ref 0.1542 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2229 _reflns_number_total 2265 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3md00357d2.cif _cod_data_source_block D8_Flu _cod_database_code 7247571 _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 20221013_D8_Flu_auto in P-1 D8_Flu.res created by SHELXL-2018/3 at 16:03:36 on 13-Oct-2022 CELL 1.54184 5.7120 9.1610 12.6671 73.270 82.917 72.913 ZERR 2.00 0.0002 0.0003 0.0005 0.003 0.003 0.003 LATT 1 SFAC C H F O D UNIT 30 10 2 4 16 MERG 2 FMAP 2 PLAN 20 HTAB CONF BOND $H ACTA L.S. 40 DELU 0.001 C13 F13 TEMP -180.00 WGHT 0.083400 0.490600 EXTI 0.014691 FVAR 15.52041 MOLE 1 C1 1 0.005918 0.799118 0.101742 11.00000 0.03333 0.02516 = 0.01656 -0.00493 -0.00219 -0.01011 C2 1 0.009876 0.644667 0.188816 11.00000 0.03380 0.02210 = 0.02155 -0.00250 -0.00127 -0.00877 AFIX 13 H2 2 0.178690 0.571425 0.188717 11.00000 -1.20000 AFIX 0 C3 1 -0.170317 0.566232 0.163014 11.00000 0.04387 0.02601 = 0.02775 -0.00474 -0.00503 -0.01364 AFIX 137 H3A 2 -0.335343 0.639314 0.158411 11.00000 -1.50000 H3B 2 -0.170310 0.469316 0.221660 11.00000 -1.50000 H3C 2 -0.120855 0.539766 0.092424 11.00000 -1.50000 AFIX 0 O1 4 0.224064 0.817366 0.067807 11.00000 0.03367 0.02991 = 0.03407 0.00493 0.00108 -0.01125 AFIX 147 H1 2 0.210195 0.905085 0.020772 11.00000 -1.50000 AFIX 0 O2 4 -0.183465 0.897960 0.069427 11.00000 0.03335 0.03159 = 0.02353 0.00117 -0.00009 -0.01446 C11 1 -0.044640 0.683862 0.299818 11.00000 0.03409 0.01678 = 0.02029 -0.00013 0.00125 -0.01214 C12 1 0.141259 0.639445 0.373084 11.00000 0.02746 0.01739 = 0.02419 -0.00108 0.00125 -0.00864 AFIX 43 D12 5 0.302423 0.583616 0.354667 11.00000 -1.20000 AFIX 0 C13 1 0.090029 0.677032 0.472788 11.00000 0.02798 0.01656 = 0.02405 -0.00062 -0.00226 -0.00944 F13 3 0.271300 0.624775 0.544859 11.00000 0.03571 0.03798 = 0.03709 -0.00724 -0.00819 -0.00805 C14 1 -0.141441 0.759671 0.504966 11.00000 0.02687 0.01553 = 0.02010 0.00000 -0.00168 -0.01001 C15 1 -0.325547 0.804379 0.429607 11.00000 0.02584 0.01969 = 0.02305 -0.00050 -0.00286 -0.00737 AFIX 43 D15 5 -0.486201 0.861277 0.447753 11.00000 -1.20000 AFIX 0 C16 1 -0.278660 0.767409 0.328784 11.00000 0.03163 0.02338 = 0.02093 0.00186 -0.00694 -0.01151 AFIX 43 D16 5 -0.407138 0.799308 0.279071 11.00000 -1.20000 AFIX 0 C21 1 -0.191942 0.795854 0.613993 11.00000 0.02500 0.01574 = 0.02143 -0.00167 -0.00459 -0.00390 C22 1 -0.048447 0.871718 0.649247 11.00000 0.02625 0.01936 = 0.02894 -0.00422 -0.00528 -0.00655 AFIX 43 D22 5 0.084487 0.900141 0.603353 11.00000 -1.20000 AFIX 0 C23 1 -0.099560 0.905684 0.751142 11.00000 0.03515 0.02600 = 0.03608 -0.01211 -0.01124 -0.00590 AFIX 43 D23 5 -0.002649 0.958419 0.774129 11.00000 -1.20000 AFIX 0 C24 1 -0.290857 0.863079 0.819254 11.00000 0.03911 0.03495 = 0.02582 -0.01370 -0.00585 -0.00327 AFIX 43 D24 5 -0.324035 0.885551 0.889136 11.00000 -1.20000 AFIX 0 C25 1 -0.434066 0.787522 0.785335 11.00000 0.02882 0.03426 = 0.02632 -0.00849 0.00052 -0.00616 AFIX 43 D25 5 -0.564779 0.757570 0.832203 11.00000 -1.20000 AFIX 0 C26 1 -0.386262 0.755551 0.682567 11.00000 0.02715 0.02346 = 0.02376 -0.00534 -0.00379 -0.00732 AFIX 43 D26 5 -0.487038 0.705827 0.659019 11.00000 -1.20000 AFIX 0 HKLF 4 REM 20221013_D8_Flu_auto in P-1 REM wR2 = 0.1542, GooF = S = 1.066, Restrained GooF = 1.069 for all data REM R1 = 0.0544 for 2229 Fo > 4sig(Fo) and 0.0548 for all 2265 data REM 166 parameters refined using 1 restraints END WGHT 0.0846 0.4950 REM Instructions for potential hydrogen bonds EQIV $1 -x, -y+2, -z HTAB O1 O2_$1 REM Highest difference peak 0.525, deepest hole -0.525, 1-sigma level 0.059 Q1 1 -0.5458 0.8769 0.4595 11.00000 0.05 0.52 Q2 1 0.0475 0.5405 0.1602 11.00000 0.05 0.41 Q3 1 -0.1630 0.6765 0.1710 11.00000 0.05 0.33 Q4 1 -0.3087 0.9718 0.0522 11.00000 0.05 0.30 Q5 1 -0.1624 0.7778 0.5585 11.00000 0.05 0.28 Q6 1 -0.0125 0.6651 0.2463 11.00000 0.05 0.27 Q7 1 -0.1570 0.8589 0.6221 11.00000 0.05 0.26 Q8 1 -0.2121 0.7919 0.4642 11.00000 0.05 0.25 Q9 1 -0.0261 0.7410 0.4848 11.00000 0.05 0.25 Q10 1 0.1055 0.6370 0.4371 11.00000 0.05 0.23 Q11 1 -0.0701 0.8878 0.7038 11.00000 0.05 0.21 Q12 1 0.0268 0.6677 0.3464 11.00000 0.05 0.20 Q13 1 0.0886 0.8492 0.0571 11.00000 0.05 0.19 Q14 1 -0.2933 0.7730 0.3831 11.00000 0.05 0.19 Q15 1 -0.4248 0.7958 0.7253 11.00000 0.05 0.19 Q16 1 -0.1176 0.8377 0.7833 11.00000 0.05 0.19 Q17 1 -0.1740 0.7238 0.3023 11.00000 0.05 0.19 Q18 1 -0.3224 0.7905 0.8026 11.00000 0.05 0.18 Q19 1 -0.3474 0.8161 0.6421 11.00000 0.05 0.18 Q20 1 -0.1165 0.9283 0.0199 11.00000 0.05 0.17 ; _shelx_res_checksum 29777 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 0.0059(4) 0.7991(2) 0.10174(14) 0.0246(4) Uani 1 1 d . . . . . C2 C 0.0099(4) 0.6447(2) 0.18882(15) 0.0263(4) Uani 1 1 d . . . . . H2 H 0.178690 0.571425 0.188717 0.032 Uiso 1 1 calc R U . . . C3 C -0.1703(4) 0.5662(2) 0.16301(17) 0.0318(5) Uani 1 1 d . . . . . H3A H -0.335343 0.639314 0.158411 0.048 Uiso 1 1 calc R U . . . H3B H -0.170310 0.469316 0.221660 0.048 Uiso 1 1 calc R U . . . H3C H -0.120855 0.539766 0.092424 0.048 Uiso 1 1 calc R U . . . O1 O 0.2241(3) 0.81737(17) 0.06781(12) 0.0351(4) Uani 1 1 d . . . . . H1 H 0.210195 0.905085 0.020772 0.053 Uiso 1 1 calc R U . . . O2 O -0.1835(3) 0.89796(16) 0.06943(11) 0.0302(4) Uani 1 1 d . . . . . C11 C -0.0446(4) 0.6839(2) 0.29982(15) 0.0238(4) Uani 1 1 d . . . . . C12 C 0.1413(3) 0.6394(2) 0.37308(15) 0.0236(4) Uani 1 1 d . . . . . D12 D 0.302423 0.583616 0.354667 0.028 Uiso 1 1 calc R U . . . C13 C 0.0900(3) 0.6770(2) 0.47279(15) 0.0230(4) Uani 1 1 d . U . . . F13 F 0.2713(2) 0.62478(15) 0.54486(10) 0.0374(4) Uani 1 1 d . U . . . C14 C -0.1414(3) 0.75967(19) 0.50497(14) 0.0209(4) Uani 1 1 d . . . . . C15 C -0.3255(3) 0.8044(2) 0.42961(15) 0.0236(4) Uani 1 1 d . . . . . D15 D -0.486201 0.861277 0.447753 0.028 Uiso 1 1 calc R U . . . C16 C -0.2787(4) 0.7674(2) 0.32878(15) 0.0256(4) Uani 1 1 d . . . . . D16 D -0.407138 0.799308 0.279071 0.031 Uiso 1 1 calc R U . . . C21 C -0.1919(3) 0.79585(19) 0.61399(14) 0.0215(4) Uani 1 1 d . . . . . C22 C -0.0484(3) 0.8717(2) 0.64925(16) 0.0249(4) Uani 1 1 d . . . . . D22 D 0.084487 0.900141 0.603353 0.030 Uiso 1 1 calc R U . . . C23 C -0.0996(4) 0.9057(2) 0.75114(17) 0.0312(5) Uani 1 1 d . . . . . D23 D -0.002649 0.958419 0.774129 0.037 Uiso 1 1 calc R U . . . C24 C -0.2909(4) 0.8631(2) 0.81925(16) 0.0332(5) Uani 1 1 d . . . . . D24 D -0.324035 0.885551 0.889136 0.040 Uiso 1 1 calc R U . . . C25 C -0.4341(4) 0.7875(2) 0.78534(16) 0.0304(5) Uani 1 1 d . . . . . D25 D -0.564779 0.757570 0.832203 0.036 Uiso 1 1 calc R U . . . C26 C -0.3863(3) 0.7556(2) 0.68257(15) 0.0246(4) Uani 1 1 d . . . . . D26 D -0.487038 0.705827 0.659019 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 0.0333(11) 0.0252(9) 0.0166(8) -0.0049(7) -0.0022(7) -0.0101(8) C2 0.0338(11) 0.0221(9) 0.0216(9) -0.0025(7) -0.0013(8) -0.0088(7) C3 0.0439(12) 0.0260(10) 0.0277(10) -0.0047(8) -0.0050(8) -0.0136(8) O1 0.0337(8) 0.0299(8) 0.0341(8) 0.0049(6) 0.0011(6) -0.0113(6) O2 0.0334(8) 0.0316(7) 0.0235(7) 0.0012(6) -0.0001(6) -0.0145(6) C11 0.0341(10) 0.0168(8) 0.0203(9) -0.0001(7) 0.0013(7) -0.0121(7) C12 0.0275(10) 0.0174(8) 0.0242(9) -0.0011(7) 0.0012(7) -0.0086(7) C13 0.0280(10) 0.0166(8) 0.0241(9) -0.0006(7) -0.0023(7) -0.0094(7) F13 0.0357(7) 0.0380(7) 0.0371(7) -0.0072(5) -0.0082(5) -0.0080(5) C14 0.0269(9) 0.0155(8) 0.0201(9) 0.0000(6) -0.0017(7) -0.0100(7) C15 0.0258(9) 0.0197(8) 0.0231(9) -0.0005(7) -0.0029(7) -0.0074(7) C16 0.0316(10) 0.0234(9) 0.0209(9) 0.0019(7) -0.0069(7) -0.0115(7) C21 0.0250(9) 0.0157(8) 0.0214(9) -0.0017(7) -0.0046(7) -0.0039(7) C22 0.0263(10) 0.0194(8) 0.0289(10) -0.0042(7) -0.0053(7) -0.0066(7) C23 0.0351(11) 0.0260(10) 0.0361(11) -0.0121(8) -0.0112(9) -0.0059(8) C24 0.0391(12) 0.0350(11) 0.0258(10) -0.0137(8) -0.0059(8) -0.0033(9) C25 0.0288(10) 0.0343(10) 0.0263(10) -0.0085(8) 0.0005(8) -0.0062(8) C26 0.0271(10) 0.0235(9) 0.0238(9) -0.0053(7) -0.0038(7) -0.0073(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' F F 0.0727 0.0534 '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' D D 0.0000 0.0000 '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 123.54(17) . . ? O2 C1 C2 122.62(17) . . ? O1 C1 C2 113.81(16) . . ? C1 C2 C11 106.84(14) . . ? C1 C2 C3 110.69(15) . . ? C11 C2 C3 113.56(16) . . ? C1 C2 H2 108.5 . . ? C11 C2 H2 108.5 . . ? C3 C2 H2 108.5 . . ? 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 118.88(17) . . ? C12 C11 C2 120.01(17) . . ? C16 C11 C2 121.10(17) . . ? C13 C12 C11 119.42(17) . . ? C13 C12 D12 120.3 . . ? C11 C12 D12 120.3 . . ? F13 C13 C12 118.06(17) . . ? F13 C13 C14 118.44(16) . . ? C12 C13 C14 123.43(17) . . ? C13 C14 C15 116.22(17) . . ? C13 C14 C21 122.14(16) . . ? C15 C14 C21 121.63(16) . . ? C16 C15 C14 121.42(17) . . ? C16 C15 D15 119.3 . . ? C14 C15 D15 119.3 . . ? C15 C16 C11 120.62(17) . . ? C15 C16 D16 119.7 . . ? C11 C16 D16 119.7 . . ? C26 C21 C22 118.86(17) . . ? C26 C21 C14 120.04(16) . . ? C22 C21 C14 121.09(17) . . ? C23 C22 C21 120.29(18) . . ? C23 C22 D22 119.9 . . ? C21 C22 D22 119.9 . . ? C24 C23 C22 120.35(18) . . ? C24 C23 D23 119.8 . . ? C22 C23 D23 119.8 . . ? C23 C24 C25 119.89(18) . . ? C23 C24 D24 120.1 . . ? C25 C24 D24 120.1 . . ? C24 C25 C26 120.01(19) . . ? C24 C25 D25 120.0 . . ? C26 C25 D25 120.0 . . ? C25 C26 C21 120.58(17) . . ? C25 C26 D26 119.7 . . ? C21 C26 D26 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 1.216(2) . ? C1 O1 1.309(2) . ? C1 C2 1.519(2) . ? C2 C11 1.523(2) . ? C2 C3 1.528(3) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? O1 H1 0.8400 . ? C11 C12 1.388(3) . ? C11 C16 1.395(3) . ? C12 C13 1.378(3) . ? C12 D12 0.9500 . ? C13 F13 1.351(2) . ? C13 C14 1.394(3) . ? C14 C15 1.398(3) . ? C14 C21 1.486(2) . ? C15 C16 1.389(3) . ? C15 D15 0.9500 . ? C16 D16 0.9500 . ? C21 C26 1.393(3) . ? C21 C22 1.399(3) . ? C22 C23 1.390(3) . ? C22 D22 0.9500 . ? C23 C24 1.384(3) . ? C23 D23 0.9500 . ? C24 C25 1.387(3) . ? C24 D24 0.9500 . ? C25 C26 1.393(3) . ? C25 D25 0.9500 . ? C26 D26 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 -77.2(2) . . . . ? O1 C1 C2 C11 100.80(18) . . . . ? O2 C1 C2 C3 46.9(2) . . . . ? O1 C1 C2 C3 -135.09(17) . . . . ? C1 C2 C11 C12 -107.09(18) . . . . ? C3 C2 C11 C12 130.59(18) . . . . ? C1 C2 C11 C16 71.5(2) . . . . ? C3 C2 C11 C16 -50.9(2) . . . . ? C16 C11 C12 C13 0.8(2) . . . . ? C2 C11 C12 C13 179.35(15) . . . . ? C11 C12 C13 F13 176.46(15) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? F13 C13 C14 C15 -176.95(14) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? F13 C13 C14 C21 1.9(2) . . . . ? C12 C13 C14 C21 178.85(15) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C21 C14 C15 C16 -178.64(15) . . . . ? C14 C15 C16 C11 0.0(3) . . . . ? C12 C11 C16 C15 -0.6(3) . . . . ? C2 C11 C16 C15 -179.12(15) . . . . ? C13 C14 C21 C26 -127.65(18) . . . . ? C15 C14 C21 C26 51.1(2) . . . . ? C13 C14 C21 C22 53.0(2) . . . . ? C15 C14 C21 C22 -128.23(18) . . . . ? C26 C21 C22 C23 0.1(3) . . . . ? C14 C21 C22 C23 179.51(16) . . . . ? C21 C22 C23 C24 0.8(3) . . . . ? C22 C23 C24 C25 -0.7(3) . . . . ? C23 C24 C25 C26 -0.4(3) . . . . ? C24 C25 C26 C21 1.4(3) . . . . ? C22 C21 C26 C25 -1.2(3) . . . . ? C14 C21 C26 C25 179.41(16) . . . . ?