Synthesis and supramolecular properties of all-<i>cis</i>-2,4,6-trifluorocyclohexane-1,3,5-triol.
Haridas, Shyamkumar V.; von Delius, Max; Chemical communications (Cambridge, England) 60 (2024) 606–609; doi:10.1039/d3cc05510h

data_7132465
_publ_section_title
;
 Synthesis and supramolecular properties of
 all-<i>cis</i>-2,4,6-trifluorocyclohexane-1,3,5-triol.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              606
_journal_page_last               609
_journal_paper_doi               10.1039/d3cc05510h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C10 H15 F3 O4'
_chemical_formula_sum            'C10 H15 F3 O4'
_chemical_formula_weight         256.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-11-06 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.47780(10)
_cell_length_b                   8.90490(10)
_cell_length_c                   19.2107(2)
_cell_measurement_reflns_used    10831
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      72.8400
_cell_measurement_theta_min      4.6340
_cell_volume                     1094.62(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -84.00  37.00   1.00    1.00    --  -43.06  19.00   0.00  121
  2  \w   -117.00 -19.00   1.00    1.00    --  -43.06 -38.00-180.00   98
  3  \w     27.00  99.00   1.00    1.00    --   43.06-125.00 150.00   72
  4  \w     27.00  99.00   1.00    1.00    --   43.06-125.00 120.00   72
  5  \w     27.00  99.00   1.00    1.00    --   43.06-125.00  30.00   72
  6  \w     32.00 131.00   1.00    1.00    --  104.94 -45.00 -90.00   99
  7  \w     33.00 134.00   1.00    1.00    --  104.94 -61.00 150.00  101
  8  \w     23.00 106.00   1.00    1.00    --  104.94 -95.00  90.00   83
  9  \w     23.00 106.00   1.00    1.00    --  104.94 -95.00 150.00   83
 10  \w    103.00 178.00   1.00    1.00    --  104.94  77.00-120.00   75
 11  \w    103.00 178.00   1.00    1.00    --  104.94  77.00-150.00   75
 12  \w     29.00 133.00   1.00    1.00    --  104.94 -30.00-120.00  104
 13  \w     32.00 112.00   1.00    1.00    --  104.94-125.00 -90.00   80
 14  \w     23.00 106.00   1.00    1.00    --  104.94 -95.00  30.00   83
 15  \w     23.00 158.00   1.00    1.00    --  104.94 -15.00  60.00  135
 16  \w     23.00 106.00   1.00    1.00    --  104.94 -95.00 -60.00   83
 17  \w   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00  60.00  100
 18  \w   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00   0.00  100
 19  \w   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00 -60.00  100
 20  \w   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00-120.00  100
 21  \w   -115.00 -15.00   1.00    1.00    --  -43.06 -57.00 120.00  100
 22  \w     76.00 177.00   1.00    1.00    --  104.94  61.00-150.00  101
 23  \w     52.00 178.00   1.00    1.00    --  104.94  15.00 150.00  126
 24  \w     76.00 165.00   1.00    1.00    --  104.94  61.00  30.00   89
 25  \w     76.00 177.00   1.00    1.00    --  104.94  61.00 -30.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0045832000
_diffrn_orient_matrix_UB_12      0.0083150000
_diffrn_orient_matrix_UB_13      -0.0803560000
_diffrn_orient_matrix_UB_21      -0.1133920000
_diffrn_orient_matrix_UB_22      -0.1524151000
_diffrn_orient_matrix_UB_23      -0.0086415000
_diffrn_orient_matrix_UB_31      -0.2122964000
_diffrn_orient_matrix_UB_32      0.0813510000
_diffrn_orient_matrix_UB_33      -0.0080095000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15359
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.001
_diffrn_reflns_theta_min         4.661
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.322
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_preparation       'Solvent layering/Methanol/n-hexane'
_exptl_crystal_recrystallization_method 'Solvent layering/Methanol/n-hexane'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0082(7)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+0.3943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2059
_reflns_number_total             2170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05510h2.cif
_cod_data_source_block           svh22076
_cod_depositor_comments
'Adding full bibliography for 7132462--7132465.cif.'
_cod_database_code               7132465
_shelx_shelxl_version_number     2018/3
_publ_section_exptl
;
Any special experimental details
;
_chemical_oxdiff_formula         'C10 H15 F3 O4'
_chemical_oxdiff_usercomment     SVH-223
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.633
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
1.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00F), C00G(H00G,H00H)
1.c Idealised Me refined as rotating group:
 C00H(H00I,H00J,H00K)
1.d Idealised tetrahedral OH refined as rotating group:
 O8(H8), O005(H005)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.696
_oxdiff_exptl_absorpt_empirical_full_min 0.679