# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TFE-Form4b
_database_code_depnum_ccdc_archive 'CCDC 2280131'
loop_
_audit_author_name
_audit_author_address
'Sarah Barnett'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_TFE-Form4b          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.585 Why? 
RESPONSE: Data collected on a crystal within a diamond anvil cell. The fraction
of diffraction space that can be collected is limited due to the cell opening
angle.
;
_vrf_PLAT051_TFE-Form4b          
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 75.74 % 
RESPONSE: Data collected at a synchrotron
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,2,2-Trifluoroethanol
_chemical_name_common            Trifluoroethanol
_chemical_melting_point          229.7
_chemical_formula_moiety         'C2 D3 F3 O'
_chemical_formula_sum            'C2 D3 F3 O'
_chemical_formula_weight         103.06


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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   4.6413(3)
_cell_length_b                   16.1899(14)
_cell_length_c                   8.557(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.691(13)
_cell_angle_gamma                90
_cell_volume                     642.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2094
_cell_measurement_theta_min      2.9680
_cell_measurement_theta_max      22.2660

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.130
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81825
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.4859
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       '4-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  Newport
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-2'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            6244
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.720
_diffrn_reflns_theta_max         22.596
_diffrn_reflns_theta_full        17.000
_diffrn_measured_fraction_theta_max 0.467
_diffrn_measured_fraction_theta_full 0.585
_diffrn_reflns_Laue_measured_fraction_max 0.467
_diffrn_reflns_Laue_measured_fraction_full 0.585
_diffrn_reflns_point_group_measured_fraction_max 0.467
_diffrn_reflns_point_group_measured_fraction_full 0.585
_reflns_number_total             1247
_reflns_number_gt                769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA - generic data aquisition software'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al, 2006)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1342P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1247
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2122
_refine_ls_wR_factor_gt          0.1807
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.150


_exptl_crystal_recrystallization_method 
'Pressurisation within a diamond anvil cell'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TFE-Form4a
_database_code_depnum_ccdc_archive 'CCDC 2280132'
loop_
_audit_author_name
_audit_author_address
'Sarah Barnett'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_TFE-Form4a          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.526 Why? 
RESPONSE: Data collected on a crystal within a diamond anvil cell. The fraction
of diffraction space that can be collected is limited due to the cell opening
angle.
;
_vrf_PLAT051_TFE-Form4a          
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 76.94 % 
RESPONSE: Data collected at a synchrotron
;
_vrf_PLAT414_TFE-Form4a          
;
PROBLEM: Short Intra D-H..H-X D1 ..D1B . 1.68 Ang. 
RESPONSE: The hydrogen-bonded hydroxyl D was left as freely refined despite the
slightly small C-O-D angle.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,2,2-Trifluoroethanol
_chemical_name_common            Trifluoroethanol
_chemical_melting_point          229.7
_chemical_formula_moiety         'C2 D3 F3 O'
_chemical_formula_sum            'C2 D3 F3 O'
_chemical_formula_weight         103.06

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   4.6540(3)
_cell_length_b                   16.2590(18)
_cell_length_c                   8.577(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.615(13)
_cell_angle_gamma                90
_cell_volume                     648.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1306
_cell_measurement_theta_min      2.9800
_cell_measurement_theta_max      22.2480

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.110
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53995
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.4859
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       '4-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  Newport
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-2'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            4006
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.994
_diffrn_reflns_theta_max         22.703
_diffrn_reflns_theta_full        17.000
_diffrn_measured_fraction_theta_max 0.380
_diffrn_measured_fraction_theta_full 0.526
_diffrn_reflns_Laue_measured_fraction_max 0.380
_diffrn_reflns_Laue_measured_fraction_full 0.526
_diffrn_reflns_point_group_measured_fraction_max 0.380
_diffrn_reflns_point_group_measured_fraction_full 0.526
_reflns_number_total             1036
_reflns_number_gt                702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA - generic data aquisition software'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al, 2006)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1508P)²+0.1504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1036
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2327
_refine_ls_wR_factor_gt          0.2013
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8038(7) 0.3075(2) 0.4887(9) 0.045(3) Uani 1 1 d . . . . .
D1A D 1.0008 0.3104 0.5283 0.054 Uiso 1 1 calc R U . . .
D1B D 0.6937 0.2771 0.5638 0.054 Uiso 1 1 calc R U . . .
O1 O 0.7981(5) 0.26527(18) 0.3498(7) 0.0425(18) Uani 1 1 d . . . . .
D1 D 0.677(11) 0.238(3) 0.382(11) 0.049(14) Uiso 1 1 d . . . . .
C2 C 0.6849(7) 0.3934(2) 0.4756(10) 0.037(2) Uani 1 1 d . . . . .
F1 F 0.4073(4) 0.39253(15) 0.4300(6) 0.0628(19) Uani 1 1 d . . . . .
F2 F 0.8219(5) 0.43834(15) 0.3718(6) 0.0594(18) Uani 1 1 d . . . . .
F3 F 0.7054(6) 0.43287(16) 0.6138(7) 0.0568(19) Uani 1 1 d . . . . .
C3 C 0.2230(7) 0.10757(19) 0.3712(10) 0.041(3) Uani 1 1 d . . . . .
D3A D 0.3166 0.0631 0.3169 0.050 Uiso 1 1 calc R U . . .
D3B D 0.0171 0.0985 0.3631 0.050 Uiso 1 1 calc R U . . .
O2 O 0.2910(5) 0.18380(16) 0.2994(6) 0.0439(16) Uani 1 1 d . . . . .
D2 D 0.146(12) 0.214(4) 0.239(11) 0.082(19) Uiso 1 1 d . . . . .
C4 C 0.3165(7) 0.10681(19) 0.5368(9) 0.040(2) Uani 1 1 d . . . . .
F4 F 0.2444(5) 0.03654(14) 0.6079(6) 0.0580(18) Uani 1 1 d . . . . .
F5 F 0.6020(4) 0.11498(16) 0.5578(6) 0.0574(18) Uani 1 1 d . . . . .
F6 F 0.1998(5) 0.16861(15) 0.6182(6) 0.0539(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.374(9) . ?
C1 C2 1.505(5) . ?
C1 D1A 0.9700 . ?
C1 D1B 0.9700 . ?
C1 D1 1.56(6) . ?
O1 D1 0.77(6) . ?
C2 F2 1.329(7) . ?
C2 F1 1.339(4) . ?
C2 F3 1.349(9) . ?
C3 O2 1.424(6) . ?
C3 C4 1.474(10) . ?
C3 D3A 0.9700 . ?
C3 D3B 0.9700 . ?
O2 D2 0.97(7) . ?
C4 F4 1.342(6) . ?
C4 F5 1.342(4) . ?
C4 F6 1.347(6) . ?

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 113.7(6) . . ?
O1 C1 D1A 108.8 . . ?
C2 C1 D1A 108.8 . . ?
O1 C1 D1B 108.8 . . ?
C2 C1 D1B 108.8 . . ?
D1A C1 D1B 107.7 . . ?
O1 C1 D1 30(3) . . ?
C2 C1 D1 120(2) . . ?
D1A C1 D1 125.2 . . ?
D1B C1 D1 79.7 . . ?
C1 O1 D1 89(6) . . ?
F2 C2 F1 106.7(5) . . ?
F2 C2 F3 107.7(3) . . ?
F1 C2 F3 107.8(4) . . ?
F2 C2 C1 112.2(5) . . ?
F1 C2 C1 111.2(3) . . ?
F3 C2 C1 111.0(6) . . ?
O2 C3 C4 111.1(4) . . ?
O2 C3 D3A 109.4 . . ?
C4 C3 D3A 109.4 . . ?
O2 C3 D3B 109.4 . . ?
C4 C3 D3B 109.4 . . ?
D3A C3 D3B 108.0 . . ?
C3 O2 D2 121(4) . . ?
F4 C4 F5 106.4(3) . . ?
F4 C4 F6 106.8(5) . . ?
F5 C4 F6 105.6(4) . . ?
F4 C4 C3 112.0(4) . . ?
F5 C4 C3 113.1(5) . . ?
F6 C4 C3 112.4(3) . . ?

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 -57.2(5) . . . . ?
O1 C1 C2 F1 62.2(7) . . . . ?
O1 C1 C2 F3 -177.8(4) . . . . ?
O2 C3 C4 F4 177.7(3) . . . . ?
O2 C3 C4 F5 -62.1(4) . . . . ?
O2 C3 C4 F6 57.4(4) . . . . ?

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 0.77(6) 2.11(5) 2.730(3) 138(8) .
O1 D1 F5 0.77(6) 2.53(7) 3.174(6) 141(5) .
C1 D1 O2 1.56(6) 2.11(5) 3.487(6) 143(4) .
C1 D1A F1 0.97 2.48 3.183(4) 129.0 1_655
C1 D1A F6 0.97 2.59 3.101(5) 112.8 1_655
C1 D1A O2 0.97 2.66 3.453(8) 139.5 4_666
C1 D1B O1 0.97 2.58 3.317(10) 132.7 4_566
O2 D2 F6 0.97(7) 2.19(7) 2.884(5) 127(5) 4_565
C3 D3A F3 0.97 2.55 3.260(8) 130.3 4_565
C3 D3B F3 0.97 2.60 3.287(7) 128.0 4_465
C3 D3B F4 0.97 2.53 3.206(4) 127.0 3_556
O2 D2 O1 0.97(7) 2.07(7) 2.694(4) 120(7) 1_455
C3 D3B F5 0.97 2.60 3.345(6) 133.5 1_455

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.152


_exptl_crystal_recrystallization_method 
'Pressurisation within a diamond anvil cell'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TFE-Form3
_database_code_depnum_ccdc_archive 'CCDC 2280133'
loop_
_audit_author_name
_audit_author_address
'Sarah Barnett'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_TFE-Form3           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.473 Why?
RESPONSE: Data collected on a crystal within a diamond anvil cell. The fraction
of diffraction space that can be collected is limited due to the cell opening
angle.
;
_vrf_PLAT051_TFE-Form3           
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 75.48 %
RESPONSE: Data collected at a synchrotron
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,2,2-Trifluoroethanol-D
_chemical_name_common            Trifluoroethanol
_chemical_melting_point          229.7
_chemical_formula_moiety         'C2 D3 F3 O'
_chemical_formula_sum            'C2 D3 F3 O'
_chemical_formula_weight         103.06

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   4.8630(4)
_cell_length_b                   33.054(7)
_cell_length_c                   8.8694(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.519(9)
_cell_angle_gamma                90
_cell_volume                     1425.2(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2934
_cell_measurement_theta_min      1.6090
_cell_measurement_theta_max      22.5950

_exptl_crystal_description       Lath
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.056
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69140
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.4859
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       '4-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  Newport
_diffrn_detector_type            'Dectris Pilatus 300K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-2'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            9835
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.626
_diffrn_reflns_theta_max         22.825
_diffrn_reflns_theta_full        17.000
_diffrn_measured_fraction_theta_max 0.370
_diffrn_measured_fraction_theta_full 0.473
_diffrn_reflns_Laue_measured_fraction_max 0.370
_diffrn_reflns_Laue_measured_fraction_full 0.473
_diffrn_reflns_point_group_measured_fraction_max 0.370
_diffrn_reflns_point_group_measured_fraction_full 0.473
_reflns_number_total             2248
_reflns_number_gt                934
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'GDA - generic data acquisition software'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al, 2006)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1111P)²+0.6280P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.2279
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 
'Pressurisation within a diamond anvil cell'
