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_7132860
_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         'C32 H45 F9 O2'
_chemical_formula_sum            'C32 H45 F9 O2'
_chemical_formula_weight         632.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 94.027(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2990(6)
_cell_length_b                   9.2607(5)
_cell_length_c                   14.5611(9)
_cell_measurement_reflns_used    4028
_cell_measurement_temperature    299.1(6)
_cell_measurement_theta_max      74.5790
_cell_measurement_theta_min      3.0270
_cell_volume                     1654.38(16)
_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      299.1(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_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     36.00  64.00   0.50    0.40    --  108.29 -61.00-150.00   56
  2  \w    -24.00  64.00   0.50    0.29    --   45.28 -72.00   3.00  176
  3  \w     45.00  89.00   0.50    0.40    --  108.29 -72.00   3.00   88
  4  \w     35.00  72.00   0.50    0.40    --  108.29 -61.00  30.00   74
  5  \w     37.00  63.00   0.50    0.40    --  108.29 -61.00 150.00   52
  6  \w    105.00 140.00   0.50    0.40    --  108.29  45.00  30.00   70
  7  \w    152.00 177.00   0.50    0.40    --  108.29  45.00  30.00   50
  8  \w    107.00 176.00   0.50    0.40    --  108.29  72.00 133.00  138
  9  \w     27.00 108.00   0.50    0.29    --   45.28  72.00 133.00  162
 10  \w    -12.00  33.00   0.50    0.29    --  -45.28  19.00 120.00   90
 11  \w    -11.00  14.00   0.50    0.29    --  -45.28  72.00 133.00   50
 12  \w    -67.00 -41.00   0.50    0.29    --  -45.28  72.00 133.00   52
 13  \w     35.00 104.00   0.50    0.40    --  108.29 -94.00-180.00  138
 14  \w     -6.00  31.00   0.50    0.29    --  -45.28  19.00 -90.00   74
 15  \w    -54.00 -29.00   0.50    0.40    -- -102.00  77.00 -30.00   50
 16  \w    -61.00 -36.00   0.50    0.40    -- -102.00  61.00 -60.00   50
 17  \w    -65.00 -32.00   0.50    0.40    -- -102.00  61.00 -30.00   66
 18  \w   -100.00 -57.00   0.50    0.40    -- -102.00  77.00 -30.00   86
 19  \w    -85.00 -45.00   0.50    0.40    -- -102.00  72.00 133.00   80
 20  \w    -55.00 -29.00   0.50    0.40    -- -102.00  61.00 120.00   52
 21  \w   -147.00 -97.00   0.50    0.40    -- -102.00 -30.00  60.00  100
 22  \w   -175.00-123.00   0.50    0.40    -- -102.00 -72.00   3.00  104
 23  \w   -147.00-121.00   0.50    0.40    -- -102.00 -45.00 -60.00   52
 24  \w   -109.00 -84.00   0.50    0.40    -- -102.00 -45.00 -60.00   50
;
_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      -0.0188261000
_diffrn_orient_matrix_UB_12      0.0514160000
_diffrn_orient_matrix_UB_13      0.0982752000
_diffrn_orient_matrix_UB_21      -0.0719482000
_diffrn_orient_matrix_UB_22      0.1243222000
_diffrn_orient_matrix_UB_23      -0.0398875000
_diffrn_orient_matrix_UB_31      -0.1011387000
_diffrn_orient_matrix_UB_32      -0.0979100000
_diffrn_orient_matrix_UB_33      0.0008153000
_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  0.0381
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10586
_diffrn_reflns_point_group_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.768
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.774
_diffrn_reflns_theta_min         3.042
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75560
_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    1.270
_exptl_crystal_description       needle
_exptl_crystal_F_000             668
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EA'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1080 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         5354
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0811
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1796P)^2^+0.0318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2260
_refine_ls_wR_factor_ref         0.2564
_reflns_Friedel_coverage         0.524
_reflns_Friedel_fraction_full    0.632
_reflns_Friedel_fraction_max     0.565
_reflns_number_gt                3692
_reflns_number_total             5354
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00840e2.cif
_cod_data_source_block           jhh-230220-1_auto
_cod_depositor_comments
'Adding full bibliography for 7132858--7132863.cif.'
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7132860
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H O N 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
 C1-C5
 1.5 with sigma of 0.02
 C00Z-C010
 1.5 with sigma of 0.02
 C00U-C1
 1.5 with sigma of 0.02
3. Rigid bond restraints
 F1, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C1, C5
 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: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: F001(0.5) HB(0.5) HC(0.5) H1(0.5) HD(0.5) C2(0.5) H2A(0.5) C3(0.5)
 H3A(0.5) H3B(0.5) H3C(0.5) C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5) C4(0.5) H4(0.5)
 C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5) C8(0.5) H8A(0.5) H8B(0.5) H8C(0.5) F6(0.5)
6.a Ternary CH refined with riding coordinates:
 C004(H004), C006(H006), C00A(H00G), C00B(H00H), C00G(H00M), C00H(H00N),
 C2(H2A), C4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C003(H00A,H00B), C008(H00C,H00D), C009(H00E,H00F), C00E(H00I,H00J), C00F(H00K,
 H00L), C00I(H00O,H00P), C00O(H00X,H00Y), C00P(H00Z,H), C00Q(H00,HA), C00R(HB,
 HC), C00R(H1,HD), C00W(H3,HG)
6.c Me refined with riding coordinates:
 C8(H8A,H8B,H8C)
6.d Aromatic/amide H refined with riding coordinates:
 C00L(H00Q)
6.e Idealised Me refined as rotating group:
 C00M(H00R,H00S,H00T), C00N(H00U,H00V,H00W), C00V(H2,HE,HF), C3(H3A,H3B,H3C),
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              45534
_shelx_hkl_checksum              73186
_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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.572