#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229385.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229385
loop_
_publ_author_name
'Betz, Richard'
'Gerber, Thomas'
'Schalekamp, Henk'
_publ_section_title
;
 4,4,4-Trifluoro-3-hydroxy-3-(trifluoromethyl)butanoic acid
;
_journal_coeditor_code           GK2344
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o616
_journal_paper_doi               10.1107/S1600536811004764
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H4 F6 O3'
_chemical_formula_moiety         'C5 H4 F6 O3'
_chemical_formula_sum            'C5 H4 F6 O3'
_chemical_formula_weight         226.08
_chemical_name_systematic
;
4,4,4-Trifluoro-3-hydroxy-3-(trifluoromethyl)butanoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.4543(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.5031(2)
_cell_length_b                   20.5490(8)
_cell_length_c                   14.0342(6)
_cell_measurement_reflns_used    9089
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.93
_cell_volume                     1569.79(11)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0093
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25936
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.447
_exptl_crystal_size_min          0.326
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.377
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.8289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                3469
_reflns_number_total             3897
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2344.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229385
_cod_database_fobs_code          2229385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.86328(18) 0.71888(5) 0.08430(10) 0.0429(3) Uani d . 1 . .
H H1 0.8645 0.6811 0.1073 0.064 Uiso calc R 1 . .
O O2 0.45964(17) 0.70927(5) 0.08404(8) 0.0326(2) Uani d . 1 . .
O O3 0.17625(19) 0.80005(7) -0.02218(11) 0.0520(4) Uani d . 1 . .
H H3 0.2000 0.7657 0.0103 0.078 Uiso calc R 1 . .
O O4 0.47274(16) 0.59040(4) 0.16029(7) 0.0285(2) Uani d . 1 . .
H H4 0.4717 0.6280 0.1367 0.043 Uiso calc R 1 . .
O O5 0.87553(17) 0.59872(5) 0.15635(8) 0.0337(2) Uani d . 1 . .
O O6 1.13316(16) 0.48391(5) 0.18383(8) 0.0316(2) Uani d . 1 . .
H H6 1.1185 0.5241 0.1733 0.047 Uiso calc R 1 . .
C C1 0.6381(2) 0.74043(6) 0.06831(9) 0.0261(2) Uani d . 1 . .
C C2 0.6189(2) 0.80980(6) 0.03285(10) 0.0281(3) Uani d . 1 . .
H H2A 0.7714 0.8211 0.0069 0.034 Uiso calc R 1 . .
H H2B 0.6071 0.8389 0.0882 0.034 Uiso calc R 1 . .
C C3 0.3986(2) 0.82251(7) -0.04523(10) 0.0301(3) Uani d . 1 . .
C C4 0.3661(3) 0.89678(8) -0.05702(13) 0.0431(4) Uani d . 1 . .
C C5 0.4440(4) 0.79138(8) -0.14087(12) 0.0477(4) Uani d . 1 . .
C C6 0.6980(2) 0.56870(6) 0.17642(9) 0.0233(2) Uani d . 1 . .
C C7 0.7220(2) 0.50386(6) 0.22712(9) 0.0246(2) Uani d . 1 . .
H H7A 0.5583 0.4829 0.2201 0.030 Uiso calc R 1 . .
H H7B 0.7761 0.5113 0.2967 0.030 Uiso calc R 1 . .
C C8 0.9032(2) 0.45714(6) 0.18926(9) 0.0237(2) Uani d . 1 . .
C C9 0.9528(3) 0.40037(7) 0.26098(11) 0.0343(3) Uani d . 1 . .
C C10 0.7933(3) 0.43236(7) 0.08834(10) 0.0333(3) Uani d . 1 . .
F F1 0.1814(3) 0.91197(7) -0.12449(13) 0.0885(5) Uani d . 1 . .
F F2 0.5634(2) 0.92505(5) -0.08100(10) 0.0611(3) Uani d . 1 . .
F F3 0.3264(3) 0.92357(6) 0.02449(11) 0.0842(5) Uani d . 1 . .
F F4 0.2561(3) 0.79879(8) -0.21017(9) 0.0852(5) Uani d . 1 . .
F F5 0.6404(2) 0.81581(6) -0.17319(8) 0.0595(3) Uani d . 1 . .
F F6 0.4835(4) 0.72803(6) -0.12768(9) 0.0885(5) Uani d . 1 . .
F F7 0.74664(19) 0.36955(5) 0.27353(8) 0.0483(2) Uani d . 1 . .
F F8 1.1068(2) 0.35676(5) 0.23401(9) 0.0582(3) Uani d . 1 . .
F F9 1.05355(19) 0.42287(5) 0.34686(7) 0.0486(3) Uani d . 1 . .
F F10 0.75894(18) 0.48279(5) 0.02779(6) 0.0430(2) Uani d . 1 . .
F F11 0.9385(2) 0.39072(6) 0.05224(8) 0.0601(3) Uani d . 1 . .
F F12 0.57504(19) 0.40413(5) 0.08745(7) 0.0503(3) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 113.34(11) ?
O2 C1 O1 . . 124.10(12) ?
O2 C1 C2 . . 122.48(11) ?
O3 C3 C2 . . 114.09(11) ?
O3 C3 C4 . . 105.15(12) ?
O3 C3 C5 . . 109.04(13) ?
O4 C6 C7 . . 113.50(10) ?
O5 C6 O4 . . 123.94(11) ?
O5 C6 C7 . . 122.50(11) ?
O6 C8 C7 . . 114.46(10) ?
O6 C8 C9 . . 105.08(10) ?
O6 C8 C10 . . 108.49(10) ?
C1 O1 H1 . . 109.5 ?
C1 C2 C3 . . 113.99(11) ?
C1 C2 H2A . . 108.8 ?
C1 C2 H2B . . 108.8 ?
C2 C3 C4 . . 108.21(12) ?
C2 C3 C5 . . 109.85(12) ?
C3 O3 H3 . . 109.5 ?
C3 C2 H2A . . 108.8 ?
C3 C2 H2B . . 108.8 ?
C5 C3 C4 . . 110.40(12) ?
C6 O4 H4 . . 109.5 ?
C6 C7 C8 . . 113.94(10) ?
C6 C7 H7A . . 108.8 ?
C6 C7 H7B . . 108.8 ?
C7 C8 C9 . . 108.03(10) ?
C7 C8 C10 . . 109.71(10) ?
C8 O6 H6 . . 109.5 ?
C8 C7 H7A . . 108.8 ?
C8 C7 H7B . . 108.8 ?
C9 C8 C10 . . 111.00(11) ?
F1 C4 C3 . . 112.06(16) ?
F2 C4 C3 . . 112.11(13) ?
F2 C4 F1 . . 106.79(14) ?
F3 C4 C3 . . 110.61(13) ?
F3 C4 F1 . . 108.40(16) ?
F3 C4 F2 . . 106.61(16) ?
F4 C5 C3 . . 112.59(17) ?
F4 C5 F5 . . 107.03(14) ?
F4 C5 F6 . . 108.05(16) ?
F5 C5 C3 . . 112.62(14) ?
F6 C5 C3 . . 109.26(13) ?
F6 C5 F5 . . 107.04(18) ?
F7 C9 C8 . . 111.95(11) ?
F8 C9 C8 . . 112.64(12) ?
F8 C9 F7 . . 107.96(13) ?
F8 C9 F9 . . 107.12(12) ?
F9 C9 C8 . . 109.80(12) ?
F9 C9 F7 . . 107.10(12) ?
F10 C10 C8 . . 109.13(11) ?
F11 C10 C8 . . 112.85(12) ?
F11 C10 F10 . . 107.19(12) ?
F11 C10 F12 . . 108.03(13) ?
F12 C10 C8 . . 112.56(11) ?
F12 C10 F10 . . 106.78(12) ?
H2A C2 H2B . . 107.6 ?
H7A C7 H7B . . 107.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.3042(16) ?
O1 H1 . 0.8400 ?
O2 C1 . 1.2192(16) ?
O3 C3 . 1.3896(16) ?
O3 H3 . 0.8400 ?
O4 C6 . 1.3055(15) ?
O4 H4 . 0.8400 ?
O5 C6 . 1.2228(15) ?
O6 C8 . 1.3920(14) ?
O6 H6 . 0.8400 ?
C1 C2 . 1.5084(17) ?
C2 C3 . 1.5325(18) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C5 . 1.540(2) ?
C3 C4 . 1.543(2) ?
C7 C6 . 1.5073(17) ?
C7 C8 . 1.5347(16) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.5387(18) ?
C8 C10 . 1.5425(19) ?
F1 C4 . 1.321(2) ?
F2 C4 . 1.3183(19) ?
F3 C4 . 1.316(2) ?
F4 C5 . 1.320(2) ?
F5 C5 . 1.330(2) ?
F6 C5 . 1.328(2) ?
F7 C9 . 1.3336(18) ?
F8 C9 . 1.3259(17) ?
F9 C9 . 1.3330(19) ?
F10 C10 . 1.3359(17) ?
F11 C10 . 1.3213(17) ?
F12 C10 . 1.3323(17) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O5 . 0.84 1.83 2.6653(14) 178
O3 H3 O2 . 0.84 2.01 2.7296(14) 144
O3 H3 O1 1_455 0.84 2.45 2.9561(15) 120
O4 H4 O2 . 0.84 1.82 2.6635(13) 178
O6 H6 O5 . 0.84 2.03 2.7502(13) 144
O6 H6 O4 1_655 0.84 2.41 2.9276(13) 121
C2 H2A O3 1_655 0.99 2.36 3.2773(16) 153
C7 H7A O6 1_455 0.99 2.32 3.2340(14) 153
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 140.99(13) ?
O2 C1 C2 C3 . . . . -41.98(19) ?
O3 C3 C4 F1 . . . . -58.76(18) ?
O3 C3 C4 F2 . . . . -178.84(14) ?
O3 C3 C4 F3 . . . . 62.33(18) ?
O3 C3 C5 F4 . . . . 52.05(17) ?
O3 C3 C5 F5 . . . . 173.18(13) ?
O3 C3 C5 F6 . . . . -68.01(19) ?
O6 C8 C9 F7 . . . . -179.87(11) ?
O6 C8 C9 F8 . . . . -57.98(15) ?
O6 C8 C9 F9 . . . . 61.31(14) ?
O6 C8 C10 F10 . . . . -63.45(14) ?
O6 C8 C10 F11 . . . . 55.60(15) ?
O6 C8 C10 F12 . . . . 178.20(11) ?
C1 C2 C3 O3 . . . . 50.06(17) ?
C1 C2 C3 C5 . . . . -72.71(15) ?
C1 C2 C3 C4 . . . . 166.70(12) ?
C2 C3 C4 F1 . . . . 178.96(14) ?
C2 C3 C4 F2 . . . . 58.88(18) ?
C2 C3 C4 F3 . . . . -59.96(18) ?
C2 C3 C5 F4 . . . . 177.75(13) ?
C2 C3 C5 F5 . . . . -61.12(17) ?
C2 C3 C5 F6 . . . . 57.69(19) ?
C4 C3 C5 F4 . . . . -63.00(18) ?
C4 C3 C5 F5 . . . . 58.14(18) ?
C4 C3 C5 F6 . . . . 176.95(16) ?
C5 C3 C4 F1 . . . . 58.71(18) ?
C5 C3 C4 F2 . . . . -61.37(19) ?
C5 C3 C4 F3 . . . . 179.80(15) ?
C6 C7 C8 O6 . . . . 50.77(14) ?
C6 C7 C8 C9 . . . . 167.43(11) ?
C6 C7 C8 C10 . . . . -71.45(13) ?
C7 C8 C9 F7 . . . . 57.53(15) ?
C7 C8 C9 F8 . . . . 179.43(12) ?
C7 C8 C9 F9 . . . . -61.29(14) ?
C7 C8 C10 F10 . . . . 62.26(14) ?
C7 C8 C10 F11 . . . . -178.69(12) ?
C7 C8 C10 F12 . . . . -56.09(15) ?
C8 C7 C6 O4 . . . . 139.87(11) ?
C8 C7 C6 O5 . . . . -42.93(17) ?
C9 C8 C10 F10 . . . . -178.42(11) ?
C9 C8 C10 F11 . . . . -59.37(15) ?
C9 C8 C10 F12 . . . . 63.22(15) ?
C10 C8 C9 F7 . . . . -62.79(15) ?
C10 C8 C9 F8 . . . . 59.10(16) ?
C10 C8 C9 F9 . . . . 178.39(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139080677
