#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:06:30 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288810 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247642.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_7247642 loop_ _publ_author_name 'Barnett, S. A.' 'Bull, C. L.' 'Funnell, N. P.' 'Allan, D. R.' _publ_section_title ; The rich structural phase behaviour of 2,2,2-trifluoroethanol ; _journal_issue 45 _journal_name_full CrystEngComm _journal_page_first 6291 _journal_page_last 6302 _journal_paper_doi 10.1039/D3CE00737E _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C2 D3 F3 O' _chemical_formula_sum 'C2 D3 F3 O' _chemical_formula_weight 103.06 _chemical_melting_point 229.7 _chemical_name_common Trifluoroethanol _chemical_name_systematic 2,2,2-Trifluoroethanol-D _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 mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2023-07-07 deposited with the CCDC. 2023-10-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.519(9) _cell_angle_gamma 90 _cell_formula_units_Z 16 _cell_length_a 4.8630(4) _cell_length_b 33.054(7) _cell_length_c 8.8694(14) _cell_measurement_reflns_used 2934 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 22.5950 _cell_measurement_theta_min 1.6090 _cell_volume 1425.2(4) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'GDA - generic data acquisition software' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_molecular_graphics 'Mercury (Macrae et al, 2006)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 295(2) _diffrn_detector 'Photon counting pixel array' _diffrn_detector_area_resol_mean 0 _diffrn_detector_type 'Dectris Pilatus 300K' _diffrn_measured_fraction_theta_full 0.473 _diffrn_measured_fraction_theta_max 0.370 _diffrn_measurement_device '4-circle \k-geometry diffractometer' _diffrn_measurement_device_type Newport _diffrn_measurement_method 'shutterless scans' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_radiation_source 'Diamond Light Source Beamline I19-2' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.4859 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_unetI/netI 0.0358 _diffrn_reflns_Laue_measured_fraction_full 0.473 _diffrn_reflns_Laue_measured_fraction_max 0.370 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 9835 _diffrn_reflns_point_group_measured_fraction_full 0.473 _diffrn_reflns_point_group_measured_fraction_max 0.370 _diffrn_reflns_theta_full 17.000 _diffrn_reflns_theta_max 22.825 _diffrn_reflns_theta_min 1.626 _exptl_absorpt_coefficient_mu 0.056 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.69140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.921 _exptl_crystal_density_meas ? _exptl_crystal_description Lath _exptl_crystal_F_000 800 _exptl_crystal_recrystallization_method 'Pressurisation within a diamond anvil cell' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.075 _refine_diff_density_max 0.198 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 233 _refine_ls_number_reflns 2248 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.1288 _refine_ls_R_factor_gt 0.0556 _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^)+(0.1111P)^2^+0.6280P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1608 _refine_ls_wR_factor_ref 0.2279 _reflns_Friedel_coverage 0.000 _reflns_number_gt 934 _reflns_number_total 2248 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00737e2.cif _cod_data_source_block TFE-Form3 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas Adding full bibliography for 7247640--7247642.cif. ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247642 _shelx_shelxl_version_number 2014/7 _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 0.989 _shelx_estimated_absorpt_t_max 0.996 _shelx_res_file ; TFE-Form3.res created by SHELXL-2014/7 TITL shelxt_a.res in P2(1)/c REM Old TITL 06_TFE_7141bar_100per_ in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.178, Rweak 0.167, Alpha 0.033, Orientation as input REM Formula found by SHELXT: C8 O16 CELL 0.48590 4.8630 33.054 8.8694 90.000 91.519 90.000 ZERR 16.000 0.0004 0.007 0.0014 0.000 0.009 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C D O F DISP C 0.0006 0.0007 1.86 DISP O 0.0036 0.0026 7.16 DISP F 0.0067 0.0045 12.28 UNIT 32 48 16 48 TEMP 22 SIZE 0.200 0.200 0.075 L.S. 5 BOND $D EQIV $1 x-1, y, z EQIV $2 x+1, y, z EQIV $3 -x, -y+1, -z+1 EQIV $4 x, -y+3/2, z+1/2 EQIV $5 x-1, -y+3/2, z+1/2 EQIV $6 -x+1, -y+1, -z+1 HTAB O2 O1 HTAB O4 O3 HTAB C1 F2_$1 HTAB C5 F7_$1 HTAB O1 O2_$2 HTAB O3 O4_$2 HTAB O2 O2_$3 HTAB O4 F12_$4 HTAB C7 F3_$4 HTAB C7 F9_$5 BIND O1 O1_$6 BIND O2 O2_$3 CONF ACTA 34 FMAP 2 PLAN 8 OMIT -4 10 3 rem EXTI refines to 0.000000 WGHT 0.111100 0.628000 FVAR 0.43442 C1 1 0.466104 0.535170 0.223474 11.00000 0.05633 0.07601 = 0.03921 0.00315 0.00595 -0.00204 AFIX 23 D1A 2 0.284268 0.540772 0.180930 11.00000 -1.20000 D1B 2 0.576481 0.523760 0.144502 11.00000 -1.20000 AFIX 0 O1 3 0.445205 0.507066 0.341319 11.00000 0.05150 0.07227 = 0.05394 0.00968 0.01233 0.00104 D1 2 0.600375 0.502054 0.369644 11.00000 0.11495 C2 1 0.595448 0.574014 0.278863 11.00000 0.05380 0.07025 = 0.04508 0.00897 0.00890 0.00851 F1 4 0.467108 0.589456 0.396337 11.00000 0.10395 0.07987 = 0.07150 -0.01674 0.02279 0.01018 F2 4 0.857868 0.569013 0.321469 11.00000 0.05871 0.08853 = 0.10014 0.00035 -0.00714 -0.00384 F3 4 0.590178 0.602274 0.170015 11.00000 0.10884 0.08389 = 0.07128 0.02516 0.00535 0.00088 C3 1 0.009219 0.431777 0.315385 11.00000 0.05941 0.04688 = 0.04860 -0.00010 0.00361 0.00310 AFIX 23 D3A 2 -0.092788 0.411403 0.369307 11.00000 -1.20000 D3B 2 0.203872 0.426045 0.329254 11.00000 -1.20000 AFIX 0 O2 3 -0.049636 0.470510 0.373847 11.00000 0.05265 0.05893 = 0.05617 -0.00995 0.01111 -0.00122 D2 2 0.098950 0.485556 0.393082 11.00000 0.09568 C4 1 -0.067599 0.430215 0.152798 11.00000 0.05420 0.06875 = 0.03798 0.00185 0.00569 0.00028 F4 4 -0.012918 0.394316 0.091259 11.00000 0.10724 0.07578 = 0.06424 -0.02690 0.00545 0.01480 F5 4 0.057339 0.458233 0.070990 11.00000 0.09482 0.09567 = 0.05054 0.01184 0.01560 -0.01561 F6 4 -0.338676 0.436457 0.128290 11.00000 0.05865 0.11327 = 0.06029 -0.00787 -0.00496 0.00524 C5 1 0.976439 0.721090 0.305990 11.00000 0.05835 0.06552 = 0.04142 0.00288 0.00262 -0.00213 AFIX 23 D5A 2 1.082220 0.735762 0.232631 11.00000 -1.20000 D5B 2 0.789344 0.718752 0.266271 11.00000 -1.20000 AFIX 0 O3 3 0.974938 0.743242 0.440578 11.00000 0.05601 0.06917 = 0.04100 -0.00510 0.00807 0.00007 D3 2 1.125170 0.752622 0.464426 11.00000 0.05739 C6 1 1.093516 0.680287 0.325150 11.00000 0.06022 0.07491 = 0.03777 -0.00802 0.00856 -0.00421 F7 4 1.359233 0.681693 0.369643 11.00000 0.05302 0.09497 = 0.09332 -0.01038 -0.00781 0.00730 F8 4 0.964236 0.657618 0.428001 11.00000 0.09274 0.07375 = 0.06279 0.00776 0.01926 -0.00977 F9 4 1.082958 0.659603 0.194179 11.00000 0.09269 0.09255 = 0.06345 -0.02458 0.01260 -0.00595 C7 1 0.543307 0.819843 0.427960 11.00000 0.05343 0.04565 = 0.05423 -0.00472 0.00049 -0.00036 AFIX 23 D7A 2 0.738987 0.825056 0.439765 11.00000 -1.20000 D7B 2 0.445884 0.840656 0.482158 11.00000 -1.20000 AFIX 0 O4 3 0.482114 0.781761 0.488441 11.00000 0.05659 0.05949 = 0.04749 0.00341 0.00375 -0.00240 D4 2 0.631078 0.762934 0.490537 11.00000 0.08850 C8 1 0.460041 0.821365 0.262529 11.00000 0.05096 0.05630 = 0.04613 -0.00259 0.00022 0.00244 F10 4 0.523611 0.857403 0.202477 11.00000 0.09308 0.06826 = 0.06371 0.01410 0.00452 -0.01218 F11 4 0.190395 0.816889 0.240257 11.00000 0.06156 0.09585 = 0.07090 0.01414 -0.01124 -0.00373 F12 4 0.582879 0.792959 0.183183 11.00000 0.10321 0.08174 = 0.05169 -0.01212 0.01227 0.02259 HKLF 4 REM shelxt_a.res in P2(1)/c REM R1 = 0.0556 for 934 Fo > 4sig(Fo) and 0.1288 for all 2248 data REM 233 parameters refined using 0 restraints END WGHT 0.1111 0.6280 REM Highest difference peak 0.198, deepest hole -0.231, 1-sigma level 0.060 Q1 1 0.7847 0.8588 0.2722 11.00000 0.05 0.20 Q2 1 0.3201 0.5727 0.0918 11.00000 0.05 0.20 Q3 1 0.7087 0.5851 0.4950 11.00000 0.05 0.19 Q4 1 0.6058 0.5508 0.2624 11.00000 0.05 0.19 Q5 1 0.3781 0.5819 0.1264 11.00000 0.05 0.19 Q6 1 0.3314 0.8201 0.0674 11.00000 0.05 0.18 Q7 1 0.4354 0.5913 0.1811 11.00000 0.05 0.18 Q8 1 0.5744 0.7178 0.5070 11.00000 0.05 0.18 ; _shelx_res_checksum 78728 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 C1 C 0.4661(10) 0.53517(19) 0.2235(6) 0.0571(14) Uani 1 1 d . . . . . D1A D 0.2843 0.5408 0.1809 0.069 Uiso 1 1 calc R U . . . D1B D 0.5765 0.5238 0.1445 0.069 Uiso 1 1 calc R U . . . O1 O 0.4452(7) 0.50707(13) 0.3413(4) 0.0590(11) Uani 1 1 d . . . . . D1 D 0.600(13) 0.502(2) 0.370(9) 0.11(3) Uiso 1 1 d . . . . . C2 C 0.5954(9) 0.57401(19) 0.2789(6) 0.0562(14) Uani 1 1 d . . . . . F1 F 0.4671(7) 0.58946(13) 0.3963(4) 0.0847(11) Uani 1 1 d . . . . . F2 F 0.8579(6) 0.56901(12) 0.3215(4) 0.0826(12) Uani 1 1 d . . . . . F3 F 0.5902(7) 0.60227(13) 0.1700(4) 0.0880(13) Uani 1 1 d . . . . . C3 C 0.0092(9) 0.43178(17) 0.3154(5) 0.0516(13) Uani 1 1 d . . . . . D3A D -0.0928 0.4114 0.3693 0.062 Uiso 1 1 calc R U . . . D3B D 0.2039 0.4260 0.3293 0.062 Uiso 1 1 calc R U . . . O2 O -0.0496(7) 0.47051(13) 0.3738(4) 0.0557(10) Uani 1 1 d . . . . . D2 D 0.099(12) 0.486(2) 0.393(7) 0.10(2) Uiso 1 1 d . . . . . C4 C -0.0676(9) 0.43021(18) 0.1528(6) 0.0536(14) Uani 1 1 d . . . . . F4 F -0.0129(7) 0.39432(13) 0.0913(4) 0.0824(12) Uani 1 1 d . . . . . F5 F 0.0573(7) 0.45823(13) 0.0710(4) 0.0801(11) Uani 1 1 d . . . . . F6 F -0.3387(6) 0.43646(12) 0.1283(4) 0.0775(11) Uani 1 1 d . . . . . C5 C 0.9764(10) 0.72109(19) 0.3060(6) 0.0551(14) Uani 1 1 d . . . . . D5A D 1.0822 0.7358 0.2326 0.066 Uiso 1 1 calc R U . . . D5B D 0.7893 0.7188 0.2663 0.066 Uiso 1 1 calc R U . . . O3 O 0.9749(7) 0.74324(12) 0.4406(4) 0.0553(10) Uani 1 1 d . . . . . D3 D 1.125(9) 0.7526(18) 0.464(6) 0.057(16) Uiso 1 1 d . . . . . C6 C 1.0935(10) 0.68029(19) 0.3251(6) 0.0575(15) Uani 1 1 d . . . . . F7 F 1.3592(6) 0.68169(12) 0.3696(4) 0.0806(12) Uani 1 1 d . . . . . F8 F 0.9642(7) 0.65762(12) 0.4280(4) 0.0761(10) Uani 1 1 d . . . . . F9 F 1.0830(7) 0.65960(13) 0.1942(4) 0.0827(12) Uani 1 1 d . . . . . C7 C 0.5433(9) 0.81984(17) 0.4280(5) 0.0511(13) Uani 1 1 d . . . . . D7A D 0.7390 0.8251 0.4398 0.061 Uiso 1 1 calc R U . . . D7B D 0.4459 0.8407 0.4822 0.061 Uiso 1 1 calc R U . . . O4 O 0.4821(7) 0.78176(13) 0.4884(4) 0.0545(10) Uani 1 1 d . . . . . D4 D 0.631(12) 0.763(2) 0.491(7) 0.09(2) Uiso 1 1 d . . . . . C8 C 0.4600(9) 0.82137(18) 0.2625(6) 0.0511(13) Uani 1 1 d . . . . . F10 F 0.5236(7) 0.85740(12) 0.2025(4) 0.0750(10) Uani 1 1 d . . . . . F11 F 0.1904(6) 0.81689(11) 0.2403(4) 0.0763(10) Uani 1 1 d . . . . . F12 F 0.5829(7) 0.79296(12) 0.1832(4) 0.0787(11) 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 C1 0.056(2) 0.076(6) 0.039(4) 0.003(2) 0.006(2) -0.002(2) O1 0.0515(16) 0.072(4) 0.054(3) 0.0097(16) 0.0123(15) 0.0010(17) C2 0.054(2) 0.070(6) 0.045(4) 0.009(2) 0.009(2) 0.009(2) F1 0.104(2) 0.080(4) 0.071(3) -0.0167(17) 0.0228(19) 0.010(2) F2 0.0587(15) 0.089(4) 0.100(3) 0.0004(18) -0.0071(16) -0.0038(17) F3 0.109(2) 0.084(4) 0.071(3) 0.0252(19) 0.0053(19) 0.001(2) C3 0.059(2) 0.047(5) 0.049(4) -0.0001(19) 0.004(2) 0.003(2) O2 0.0526(16) 0.059(4) 0.056(3) -0.0099(15) 0.0111(15) -0.0012(17) C4 0.054(2) 0.069(5) 0.038(4) 0.002(2) 0.006(2) 0.000(3) F4 0.107(2) 0.076(4) 0.064(3) -0.0269(17) 0.0055(18) 0.015(2) F5 0.095(2) 0.096(4) 0.051(2) 0.0118(15) 0.0156(16) -0.016(2) F6 0.0587(15) 0.113(4) 0.060(2) -0.0079(15) -0.0050(14) 0.0052(16) C5 0.058(2) 0.066(5) 0.041(4) 0.003(2) 0.003(2) -0.002(2) O3 0.0560(17) 0.069(4) 0.041(2) -0.0051(15) 0.0081(15) 0.0001(18) C6 0.060(3) 0.075(6) 0.038(4) -0.008(2) 0.009(2) -0.004(3) F7 0.0530(14) 0.095(4) 0.093(3) -0.0104(18) -0.0078(15) 0.0073(15) F8 0.0927(19) 0.074(4) 0.063(3) 0.0078(15) 0.0193(16) -0.0098(18) F9 0.093(2) 0.093(4) 0.063(3) -0.0246(18) 0.0126(17) -0.006(2) C7 0.053(2) 0.046(5) 0.054(4) -0.005(2) 0.000(2) 0.000(2) O4 0.0566(16) 0.059(4) 0.047(3) 0.0034(15) 0.0038(14) -0.0024(17) C8 0.051(2) 0.056(5) 0.046(4) -0.003(2) 0.000(2) 0.002(2) F10 0.093(2) 0.068(3) 0.064(3) 0.0141(15) 0.0045(16) -0.0122(18) F11 0.0616(16) 0.096(4) 0.071(3) 0.0141(17) -0.0112(15) -0.0037(16) F12 0.103(2) 0.082(4) 0.052(3) -0.0121(14) 0.0123(16) 0.0226(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0006 0.0007 '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' O O 0.0036 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0067 0.0045 '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 O1 C1 C2 111.0(5) . . ? O1 C1 D1A 109.4 . . ? C2 C1 D1A 109.4 . . ? O1 C1 D1B 109.4 . . ? C2 C1 D1B 109.4 . . ? D1A C1 D1B 108.0 . . ? C1 O1 O1 144.8(5) . 3_666 ? C1 O1 D1 106(5) . . ? O1 O1 D1 61(5) 3_666 . ? F1 C2 F2 106.9(5) . . ? F1 C2 F3 107.2(5) . . ? F2 C2 F3 106.9(4) . . ? F1 C2 C1 112.5(4) . . ? F2 C2 C1 112.1(5) . . ? F3 C2 C1 111.0(5) . . ? O2 C3 C4 109.9(4) . . ? O2 C3 D3A 109.7 . . ? C4 C3 D3A 109.7 . . ? O2 C3 D3B 109.7 . . ? C4 C3 D3B 109.7 . . ? D3A C3 D3B 108.2 . . ? C3 O2 O2 146.4(3) . 3_566 ? C3 O2 D2 114(4) . . ? O2 O2 D2 52(4) 3_566 . ? F5 C4 F4 107.2(4) . . ? F5 C4 F6 105.3(4) . . ? F4 C4 F6 106.0(4) . . ? F5 C4 C3 113.5(5) . . ? F4 C4 C3 112.4(5) . . ? F6 C4 C3 111.9(4) . . ? O3 C5 C6 113.0(4) . . ? O3 C5 D5A 109.0 . . ? C6 C5 D5A 109.0 . . ? O3 C5 D5B 109.0 . . ? C6 C5 D5B 109.0 . . ? D5A C5 D5B 107.8 . . ? C5 O3 D3 113(4) . . ? F7 C6 F9 106.6(4) . . ? F7 C6 F8 106.4(5) . . ? F9 C6 F8 107.1(5) . . ? F7 C6 C5 111.6(5) . . ? F9 C6 C5 111.1(5) . . ? F8 C6 C5 113.7(4) . . ? O4 C7 C8 110.3(4) . . ? O4 C7 D7A 109.6 . . ? C8 C7 D7A 109.6 . . ? O4 C7 D7B 109.6 . . ? C8 C7 D7B 109.6 . . ? D7A C7 D7B 108.1 . . ? C7 O4 D4 115(4) . . ? F12 C8 F11 107.4(4) . . ? F12 C8 F10 107.8(4) . . ? F11 C8 F10 106.0(4) . . ? F12 C8 C7 112.3(4) . . ? F11 C8 C7 112.2(4) . . ? F10 C8 C7 110.8(4) . . ? 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 O1 1.404(7) . ? C1 C2 1.506(9) . ? C1 D1A 0.9700 . ? C1 D1B 0.9700 . ? O1 O1 2.889(7) 3_666 ? O1 D1 0.81(7) . ? C2 F1 1.330(6) . ? C2 F2 1.332(6) . ? C2 F3 1.343(7) . ? C3 O2 1.413(6) . ? C3 C4 1.481(7) . ? C3 D3A 0.9700 . ? C3 D3B 0.9700 . ? O2 O2 2.997(7) 3_566 ? O2 D2 0.89(6) . ? C4 F5 1.333(6) . ? C4 F4 1.336(7) . ? C4 F6 1.346(5) . ? C5 O3 1.401(6) . ? C5 C6 1.472(9) . ? C5 D5A 0.9700 . ? C5 D5B 0.9700 . ? O3 D3 0.82(5) . ? C6 F7 1.342(6) . ? C6 F9 1.348(6) . ? C6 F8 1.349(6) . ? C7 O4 1.403(6) . ? C7 C8 1.513(7) . ? C7 D7A 0.9700 . ? C7 D7B 0.9700 . ? O4 D4 0.95(7) . ? C8 F12 1.325(6) . ? C8 F11 1.329(5) . ? C8 F10 1.344(6) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 D2 O1 0.89(6) 1.90(6) 2.715(5) 152(6) . O4 D4 O3 0.95(7) 1.86(6) 2.757(5) 156(6) . C1 D1A F2 0.97 2.62 3.300(6) 127.4 1_455 C5 D5B F7 0.97 2.61 3.334(6) 131.5 1_455 O1 D1 O2 0.81(7) 2.00(7) 2.746(5) 155(8) 1_655 O3 D3 O4 0.82(5) 1.99(5) 2.798(5) 169(6) 1_655 O2 D2 O2 0.89(6) 2.54(7) 2.997(7) 112(5) 3_566 O4 D4 F12 0.95(7) 2.53(7) 3.046(5) 114(4) 4_576 C7 D7B F3 0.97 2.60 3.356(6) 134.8 4_576 C7 D7B F9 0.97 2.61 3.366(6) 134.6 4_476 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 C2 C1 O1 O1 -0.2(8) . . . 3_666 ? O1 C1 C2 F1 -53.7(6) . . . . ? O1 C1 C2 F2 66.8(5) . . . . ? O1 C1 C2 F3 -173.8(4) . . . . ? C4 C3 O2 O2 -163.0(5) . . . 3_566 ? O2 C3 C4 F5 57.3(5) . . . . ? O2 C3 C4 F4 179.2(4) . . . . ? O2 C3 C4 F6 -61.7(6) . . . . ? O3 C5 C6 F7 -63.2(5) . . . . ? O3 C5 C6 F9 178.0(4) . . . . ? O3 C5 C6 F8 57.2(6) . . . . ? O4 C7 C8 F12 -57.9(5) . . . . ? O4 C7 C8 F11 63.1(6) . . . . ? O4 C7 C8 F10 -178.6(4) . . . . ?