Modulating the ferroelectric phases in cholesteryl-based organic compounds with perfluoroalkyl tail engineering.
Jiang, Huan-Huan; Zhang, Nan; Mao, Wei-Xin; Lan, Jin-Fei; Zhou, Long-Xing; Xu, Hua-Ming; Zhang, Han-Yue; Liao, Wei-Qiang; Chemical communications (Cambridge, England) 60 (2024) 4322–4325; doi:10.1039/d4cc00840e

data_7132862
_publ_section_title
;
 Modulating the ferroelectric phases in cholesteryl-based organic
 compounds with perfluoroalkyl tail engineering.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4322
_journal_page_last               4325
_journal_paper_doi               10.1039/d4cc00840e
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C33 H45 F11 O2'
_chemical_formula_sum            'C33 H45 F11 O2'
_chemical_formula_weight         682.69
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-05-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-01-01 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2360(4)
_cell_length_b                   12.5420(4)
_cell_length_c                   29.3792(10)
_cell_measurement_reflns_used    5238
_cell_measurement_temperature    295(5)
_cell_measurement_theta_max      70.2580
_cell_measurement_theta_min      3.0080
_cell_volume                     3403.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.957
_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   -147.00 -94.00   0.50    1.00    -- -102.00 -94.00 134.00  106
  2  \w    -13.00  20.00   0.50    0.40    --  -45.28  19.00 150.00   66
  3  \w    -40.00  26.00   0.50    0.40    --  -45.28  37.00 -90.00  132
  4  \w   -162.00 -86.00   0.50    1.00    -- -102.00 -49.00-122.00  152
  5  \w     39.00  72.00   0.50    1.00    --  108.29 -61.00  60.00   66
  6  \w     35.00  73.00   0.50    1.00    --  108.29 -61.00  30.00   76
  7  \w     39.00  64.00   0.50    1.00    --  108.29 -61.00 -30.00   50
  8  \w     41.00  67.00   0.50    1.00    --  108.29 -61.00-150.00   52
  9  \w     43.00  68.00   0.50    1.00    --  108.29 -61.00-180.00   50
 10  \w    -21.00  20.00   0.50    0.40    --   45.28 -84.00  27.00   82
 11  \w     22.00  73.00   0.50    0.40    --   45.28 -84.00  27.00  102
 12  \w     56.00 102.00   0.50    1.00    --  108.29 -94.00 134.00   92
 13  \w     36.00 105.00   0.50    1.00    --  108.29 -94.00  30.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0663655000
_diffrn_orient_matrix_UB_12      0.0046303000
_diffrn_orient_matrix_UB_13      -0.0480795000
_diffrn_orient_matrix_UB_21      0.0748790000
_diffrn_orient_matrix_UB_22      0.1080326000
_diffrn_orient_matrix_UB_23      -0.0083021000
_diffrn_orient_matrix_UB_31      0.1333765000
_diffrn_orient_matrix_UB_32      -0.0583376000
_diffrn_orient_matrix_UB_33      -0.0192479000
_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  0.0211
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            12654
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.615
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EA'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1529 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6256
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0817
_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^)+(0.1772P)^2^+0.3692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2499
_refine_ls_wR_factor_ref         0.2702
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_full    0.847
_reflns_Friedel_fraction_max     0.766
_reflns_number_gt                4820
_reflns_number_total             6256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00840e2.cif
_cod_data_source_block           jhh-230301-2-300k_auto
_cod_depositor_comments
'Adding full bibliography for 7132858--7132863.cif.'
_cod_database_code               7132862
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'c h o f'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3-C1 \\sim C3A-C1
 with sigma of 0.02
 C3-C2 \\sim C3A-C2
 with sigma of 0.02
 F31-C6 \\sim F31A-C6
 with sigma of 0.02
3. Rigid bond restraints
 C8, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of
0.02 and sigma for terminal atoms of 0.02
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Others
 Sof(F31A)=1-FVAR(1)
 Sof(F31)=FVAR(1)
 Fixed Sof: H21A(0.5) H21B(0.5) H21C(0.5) H21D(0.5) F12(0.75) C3(0.5) H3A(0.5)
 H3B(0.5) H3C(0.5) C1(0.5) H1(0.5) C5(0.75) H5A(0.75) H5B(0.75) H5C(0.75)
 C11(0.25) H11A(0.25) H11B(0.25) H11C(0.25) C2(0.5) H3D(0.5) F2(0.25) C3A(0.5)
 H3AA(0.5) H3AB(0.5) H3AC(0.5)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C23(H23), C14(H14), C32(H32), C18(H18), C36(H36), C1(H1), C2(H3D)
6.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C16(H16A,H16B), C17(H17A,H17B), C31(H31A,H31B), C13(H13A,
 H13B), C19(H19A,H19B), C20(H20A,H20B), C26(H26A,H26B), C21(H21A,H21B),
 C21(H21C,H21D), C34(H34A,H34B), C35(H35A,H35B)
6.c Me refined with riding coordinates:
 C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC)
6.d Aromatic/amide H refined with riding coordinates:
 C28(H28)
6.e Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C5(H5A,H5B,
 H5C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              77817
_shelx_hkl_checksum              94932
_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 1.139
_oxdiff_exptl_absorpt_empirical_full_min 0.843