#------------------------------------------------------------------------------ #$Date: 2023-11-02 01:41:32 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287230 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247640.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_7247640 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_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00737E _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 _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 91.691(13) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 4.6413(3) _cell_length_b 16.1899(14) _cell_length_c 8.557(4) _cell_measurement_reflns_used 2094 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 22.2660 _cell_measurement_theta_min 2.9680 _cell_volume 642.7(3) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'GDA - generic data aquisition software' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _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 0.585 _diffrn_measured_fraction_theta_max 0.467 _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 0.0510 _diffrn_reflns_av_unetI/netI 0.0388 _diffrn_reflns_Laue_measured_fraction_full 0.585 _diffrn_reflns_Laue_measured_fraction_max 0.467 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 6244 _diffrn_reflns_point_group_measured_fraction_full 0.585 _diffrn_reflns_point_group_measured_fraction_max 0.467 _diffrn_reflns_theta_full 17.000 _diffrn_reflns_theta_max 22.596 _diffrn_reflns_theta_min 1.720 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81825 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 2.130 _exptl_crystal_density_meas ? _exptl_crystal_description Plate _exptl_crystal_F_000 400 _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 0.481 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.150 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 117 _refine_ls_number_reflns 1247 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0693 _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^)+(0.1342P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1807 _refine_ls_wR_factor_ref 0.2122 _reflns_Friedel_coverage 0.000 _reflns_number_gt 769 _reflns_number_total 1247 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00737e2.cif _cod_data_source_block TFE-Form4b _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 ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7247640 _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 0.988 _shelx_estimated_absorpt_t_max 0.995 _shelx_res_file ; TFE-Form4b.res created by SHELXL-2014/7 TITL TFE_III_2_ in P2(1)/c CELL 0.48590 4.6413 16.1899 8.5566 90.000 91.691 90.000 ZERR 8.00 0.0003 0.0014 0.0041 0.000 0.013 0.000 LATT 1 SYMM -x, y+1/2,-z+1/2 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 16 24 8 24 TEMP 22 SIZE 0.200 0.200 0.075 L.S. 5 BOND $H CONF ACTA 34 FMAP 2 PLAN 8 EQIV $1 x+1, y, z EQIV $2 x+1, -y+1/2, z+1/2 EQIV $3 x, -y+1/2, z+1/2 EQIV $4 x, -y+1/2, z-1/2 EQIV $5 x-1, -y+1/2, z-1/2 EQIV $6 -x, -y, -z+1 EQIV $7 x-1, y, z HTAB O1 O2 HTAB O1 F5 HTAB C1 O2 HTAB C1 F1_$1 HTAB C1 F6_$1 HTAB C1 O2_$2 HTAB C1 O1_$3 HTAB O2 F6_$4 HTAB C3 F3_$4 HTAB C3 F3_$5 HTAB C3 F4_$6 HTAB O2 O1_$7 HTAB C3 F5_$7 OMIT 2 7 4 OMIT 2 2 0 WGHT 0.134200 FVAR 6.53706 C1 1 0.804193 0.307612 0.489902 11.00000 0.03376 0.03483 = 0.05142 0.00293 0.00113 0.00085 AFIX 23 D1A 2 1.001146 0.310276 0.530771 11.00000 -1.20000 D1B 2 0.691800 0.277063 0.564239 11.00000 -1.20000 AFIX 0 O1 3 0.799640 0.265214 0.347838 11.00000 0.03124 0.03992 = 0.06391 -0.00544 0.00568 -0.00064 D1 2 0.661934 0.234209 0.361510 11.00000 0.11055 C2 1 0.686210 0.393777 0.475415 11.00000 0.03017 0.03825 = 0.01830 -0.00104 0.00110 -0.00061 F1 4 0.405829 0.392757 0.429484 11.00000 0.02941 0.06202 = 0.06724 0.00057 -0.00422 0.00552 F2 4 0.822527 0.439379 0.371395 11.00000 0.04602 0.04750 = 0.05601 0.01326 0.00873 -0.00299 F3 4 0.704565 0.433092 0.613862 11.00000 0.06668 0.05151 = 0.04708 -0.01466 0.00513 0.00139 C3 1 0.223604 0.106743 0.372198 11.00000 0.03534 0.03589 = 0.02322 -0.00142 0.00040 -0.00261 AFIX 23 D3A 2 0.316942 0.061728 0.318593 11.00000 -1.20000 D3B 2 0.017040 0.097815 0.364137 11.00000 -1.20000 AFIX 0 O2 3 0.292746 0.183256 0.298036 11.00000 0.02980 0.04012 = 0.03919 0.00654 0.00426 0.00150 D2 2 0.175714 0.214756 0.300455 11.00000 0.06037 C4 1 0.316751 0.106562 0.537270 11.00000 0.02987 0.02789 = 0.05234 -0.00255 0.00228 -0.00055 F4 4 0.244312 0.036400 0.610296 11.00000 0.05528 0.04052 = 0.05844 0.00971 0.00385 -0.00678 F5 4 0.605031 0.114279 0.557023 11.00000 0.02995 0.06236 = 0.06013 0.00211 -0.00471 -0.00178 F6 4 0.201353 0.168995 0.618268 11.00000 0.05868 0.04429 = 0.06104 -0.01050 0.00491 0.01507 HKLF 4 REM TFE_III_2_ in P2(1)/c REM R1 = 0.0693 for 769 Fo > 4sig(Fo) and 0.1064 for all 1247 data REM 117 parameters refined using 0 restraints END WGHT 0.1342 0.0000 REM Highest difference peak 0.481, deepest hole -0.387, 1-sigma level 0.150 Q1 1 0.2768 0.1376 0.3220 11.00000 0.05 0.48 Q2 1 0.7493 0.3508 0.4743 11.00000 0.05 0.48 Q3 1 0.2446 0.0756 0.5584 11.00000 0.05 0.43 Q4 1 0.2361 0.1402 0.5001 11.00000 0.05 0.42 Q5 1 0.7311 0.3908 0.6141 11.00000 0.05 0.40 Q6 1 0.7419 0.4364 0.4932 11.00000 0.05 0.39 Q7 1 0.2570 0.2026 0.5239 11.00000 0.05 0.39 Q8 1 0.7339 0.4713 0.4319 11.00000 0.05 0.36 ; _shelx_res_checksum 59598 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 0.8042(6) 0.30761(18) 0.4899(8) 0.040(2) Uani 1 1 d . . . . . D1A D 1.0011 0.3103 0.5308 0.048 Uiso 1 1 calc R U . . . D1B D 0.6918 0.2771 0.5642 0.048 Uiso 1 1 calc R U . . . O1 O 0.7996(4) 0.26521(14) 0.3478(6) 0.0449(17) Uani 1 1 d . . . . . D1 D 0.662(12) 0.234(3) 0.362(14) 0.11(2) Uiso 1 1 d . . . . . C2 C 0.6862(6) 0.39378(17) 0.4754(8) 0.0289(19) Uani 1 1 d . . . . . F1 F 0.4058(3) 0.39276(12) 0.4295(5) 0.0530(15) Uani 1 1 d . . . . . F2 F 0.8225(4) 0.43938(12) 0.3714(5) 0.0497(16) Uani 1 1 d . . . . . F3 F 0.7046(5) 0.43309(13) 0.6139(6) 0.0550(17) Uani 1 1 d . . . . . C3 C 0.2236(6) 0.10674(15) 0.3722(8) 0.031(2) Uani 1 1 d . . . . . D3A D 0.3169 0.0617 0.3186 0.038 Uiso 1 1 calc R U . . . D3B D 0.0170 0.0978 0.3641 0.038 Uiso 1 1 calc R U . . . O2 O 0.2927(4) 0.18326(13) 0.2980(5) 0.0363(13) Uani 1 1 d . . . . . D2 D 0.176(9) 0.215(3) 0.300(9) 0.060(14) Uiso 1 1 d . . . . . C4 C 0.3168(6) 0.10656(15) 0.5373(8) 0.037(2) Uani 1 1 d . . . . . F4 F 0.2443(4) 0.03640(11) 0.6103(5) 0.0514(13) Uani 1 1 d . . . . . F5 F 0.6050(4) 0.11428(13) 0.5570(5) 0.0509(15) Uani 1 1 d . . . . . F6 F 0.2014(4) 0.16900(12) 0.6183(5) 0.0546(15) 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 0.0338(12) 0.0348(15) 0.051(7) 0.0029(18) 0.0011(19) 0.0009(10) O1 0.0312(9) 0.0399(12) 0.064(6) -0.0054(15) 0.0057(14) -0.0006(7) C2 0.0302(11) 0.0383(15) 0.018(7) -0.0010(16) 0.0011(17) -0.0006(9) F1 0.0294(8) 0.0620(13) 0.067(5) 0.0006(13) -0.0042(13) 0.0055(7) F2 0.0460(10) 0.0475(11) 0.056(5) 0.0133(12) 0.0087(14) -0.0030(7) F3 0.0667(13) 0.0515(13) 0.047(6) -0.0147(14) 0.0051(17) 0.0014(9) C3 0.0353(12) 0.0359(16) 0.023(7) -0.0014(16) 0.000(2) -0.0026(9) O2 0.0298(8) 0.0401(11) 0.039(4) 0.0065(12) 0.0043(12) 0.0015(7) C4 0.0299(11) 0.0279(14) 0.052(7) -0.0025(15) 0.002(2) -0.0005(8) F4 0.0553(10) 0.0405(10) 0.058(4) 0.0097(11) 0.0038(14) -0.0068(7) F5 0.0300(8) 0.0624(13) 0.060(5) 0.0021(14) -0.0047(13) -0.0018(7) F6 0.0587(11) 0.0443(11) 0.061(5) -0.0105(12) 0.0049(15) 0.0151(8) 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 112.9(5) . . ? O1 C1 D1A 109.0 . . ? C2 C1 D1A 109.0 . . ? O1 C1 D1B 109.0 . . ? C2 C1 D1B 109.0 . . ? D1A C1 D1B 107.8 . . ? C1 O1 D1 100(8) . . ? F2 C2 F3 107.9(3) . . ? F2 C2 F1 106.6(4) . . ? F3 C2 F1 107.3(3) . . ? F2 C2 C1 113.0(4) . . ? F3 C2 C1 110.7(5) . . ? F1 C2 C1 111.0(2) . . ? O2 C3 C4 111.4(3) . . ? O2 C3 D3A 109.3 . . ? C4 C3 D3A 109.3 . . ? O2 C3 D3B 109.3 . . ? C4 C3 D3B 109.3 . . ? D3A C3 D3B 108.0 . . ? C3 O2 D2 114(4) . . ? F4 C4 F6 106.7(4) . . ? F4 C4 F5 106.3(3) . . ? F6 C4 F5 105.9(3) . . ? F4 C4 C3 112.3(3) . . ? F6 C4 C3 112.6(3) . . ? F5 C4 C3 112.6(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 1.396(7) . ? C1 C2 1.502(4) . ? C1 D1A 0.9700 . ? C1 D1B 0.9700 . ? O1 D1 0.82(6) . ? C2 F2 1.331(6) . ? C2 F3 1.345(8) . ? C2 F1 1.348(4) . ? C3 O2 1.433(4) . ? C3 C4 1.465(8) . ? C3 D3A 0.9700 . ? C3 D3B 0.9700 . ? O2 D2 0.75(5) . ? C4 F4 1.344(5) . ? C4 F6 1.346(5) . ? C4 F5 1.349(3) . ? 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 O1 D1 O2 0.82(6) 1.96(6) 2.724(3) 153(10) . O1 D1 F5 0.82(6) 2.58(8) 3.176(5) 130(8) . C1 D1A F1 0.97 2.48 3.170(3) 127.8 1_655 C1 D1A F6 0.97 2.57 3.086(4) 113.2 1_655 C1 D1A O2 0.97 2.62 3.430(6) 140.5 4_666 C1 D1B O1 0.97 2.56 3.282(8) 131.7 4_566 O2 D2 F6 0.75(5) 2.45(6) 2.869(4) 117(5) 4_565 C3 D3A F3 0.97 2.55 3.252(7) 129.4 4_565 C3 D3B F3 0.97 2.60 3.285(7) 127.8 4_465 C3 D3B F4 0.97 2.50 3.183(3) 127.2 3_556 O2 D2 O1 0.75(5) 1.98(5) 2.690(3) 159(6) 1_455 C3 D3B F5 0.97 2.58 3.321(5) 133.6 1_455 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 O1 C1 C2 F2 -56.6(4) . . . . ? O1 C1 C2 F3 -177.8(3) . . . . ? O1 C1 C2 F1 63.1(5) . . . . ? O2 C3 C4 F4 177.7(2) . . . . ? O2 C3 C4 F6 57.3(4) . . . . ? O2 C3 C4 F5 -62.3(3) . . . . ?