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_7132858
_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         'C30 H45 F5 O2'
_chemical_formula_sum            'C30 H45 F5 O2'
_chemical_formula_weight         532.66
_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     dual
_audit_creation_date             2023-05-30
_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                 105.661(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4586(2)
_cell_length_b                   9.2797(2)
_cell_length_c                   13.4386(3)
_cell_measurement_reflns_used    15472
_cell_measurement_temperature    476(200)
_cell_measurement_theta_max      76.0270
_cell_measurement_theta_min      3.3880
_cell_volume                     1495.99(5)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_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     28.00  66.00   0.50    0.06    --   45.15  77.00 150.00   76
  2  \w     19.00  52.00   0.50    0.06    --   45.15  77.00 120.00   66
  3  \w     19.00  81.00   0.50    0.06    --   45.15  77.00  60.00  124
  4  \w     33.00  84.00   0.50    0.06    --   45.15  37.00  30.00  102
  5  \w     84.00 110.00   0.50    0.06    --   45.15   5.00   3.00   52
  6  \w     25.00  69.00   0.50    0.06    --   45.15  19.00-180.00   88
  7  \w     92.00 132.00   0.50    0.25    --  108.29   5.00   3.00   80
  8  \w     83.00 109.00   0.50    0.25    --  108.29  77.00  90.00   52
  9  \w     82.00 113.00   0.50    0.25    --  108.29  77.00 150.00   62
 10  \w    134.00 159.00   0.50    0.25    --  108.29  77.00  90.00   50
 11  \w     47.00  72.00   0.50    0.25    --  108.29 -61.00   0.00   50
 12  \w     44.00  69.00   0.50    0.25    --  108.29 -61.00  60.00   50
 13  \w    -13.00  28.00   0.50    0.06    --   45.15 -19.00  90.00   82
 14  \w    151.00 178.00   0.50    0.25    --  108.29  -5.00-173.00   54
 15  \w     67.00  97.00   0.50    0.25    --  108.29 -94.00-150.00   60
 16  \w     39.00  64.00   0.50    0.25    --  108.29 -94.00-150.00   50
 17  \w     21.00  94.00   0.50    0.06    --   45.15-125.00  30.00  146
 18  \w     39.00  64.00   0.50    0.25    --  108.29-125.00 120.00   50
 19  \w     47.00 110.00   0.50    0.25    --  108.29-125.00 150.00  126
 20  \w     76.00 111.00   0.50    0.25    --  108.29-125.00 120.00   70
 21  \w     35.00  91.00   0.50    0.25    --  108.29 -94.00 150.00  112
 22  \w    -45.00 -19.00   0.50    0.06    --  -45.15 -77.00  90.00   52
 23  \w   -116.00 -27.00   0.50    0.06    --  -45.15 -47.00  58.22  178
 24  \w   -100.00 -28.00   0.50    0.06    --  -45.15 -57.00-180.00  144
 25  \w    -73.00 -34.00   0.50    0.06    --  -45.15  -5.00-173.00   78
 26  \w   -121.00 -70.00   0.50    0.25    -- -102.00  -5.00-173.00  102
 27  \w   -101.00 -76.00   0.50    0.25    -- -102.00 -77.00-180.00   50
 28  \w   -175.00-111.00   0.50    0.25    -- -102.00 -77.00-150.00  128
 29  \w   -103.00 -78.00   0.50    0.25    -- -102.00 -77.00-150.00   50
 30  \w   -101.00 -76.00   0.50    0.25    -- -102.00 -77.00  30.00   50
 31  \w   -109.00 -76.00   0.50    0.25    -- -102.00 -77.00  90.00   66
 32  \w   -102.00 -77.00   0.50    0.25    -- -102.00 -77.00 120.00   50
 33  \w   -102.00 -77.00   0.50    0.25    -- -102.00 -77.00 150.00   50
 34  \w   -103.00 -78.00   0.50    0.25    -- -102.00 -75.00  53.22   50
 35  \w   -103.00 -77.00   0.50    0.25    -- -102.00 -74.00  37.80   52
 36  \w   -107.00 -79.00   0.50    0.25    -- -102.00 -75.00  83.65   56
 37  \w   -154.00-128.00   0.50    0.25    -- -102.00 -72.00 149.81   52
 38  \w   -174.00-148.00   0.50    0.25    -- -102.00 -75.00  53.22   52
 39  \w   -174.00-149.00   0.50    0.25    -- -102.00 -77.00  30.00   50
 40  \w   -173.00 -78.00   0.50    0.25    -- -102.00 -72.00  68.34  190
 41  \w   -103.00 -78.00   0.50    0.25    -- -102.00 -71.00 115.00   50
 42  \w   -103.00 -78.00   0.50    0.25    -- -102.00 -71.00 121.91   50
 43  \w   -123.00 -78.00   0.50    0.25    -- -102.00 -72.00 149.81   90
 44  \w   -167.00-142.00   0.50    0.25    -- -102.00 -71.00  90.86   50
 45  \w   -169.00-143.00   0.50    0.25    -- -102.00 -70.00 127.99   52
 46  \w   -105.00 -79.00   0.50    0.25    -- -102.00 -70.00 127.99   52
 47  \w   -104.00 -79.00   0.50    0.25    -- -102.00 -69.00  97.18   50
 48  \w   -103.00 -78.00   0.50    0.25    -- -102.00 -71.00  90.86   50
 49  \w   -104.00 -79.00   0.50    0.25    -- -102.00 -69.00  90.37   50
 50  \w   -104.00 -79.00   0.50    0.25    -- -102.00 -70.00  73.49   50
 51  \w   -103.00 -78.00   0.50    0.25    -- -102.00 -71.00  39.27   50
 52  \w   -106.00 -81.00   0.50    0.25    -- -102.00 -65.00  49.49   50
 53  \w   -109.00 -84.00   0.50    0.25    -- -102.00 -61.00 150.00   50
 54  \w   -165.00-140.00   0.50    0.25    -- -102.00 -69.00  97.18   50
 55  \w   -173.00-147.00   0.50    0.25    -- -102.00 -65.00  49.49   52
 56  \w   -108.00 -83.00   0.50    0.25    -- -102.00 -59.00  92.74   50
 57  \w   -174.00 -83.00   0.50    0.25    -- -102.00 -55.00 145.26  182
 58  \w   -175.00 -83.00   0.50    0.25    -- -102.00 -55.00 115.60  184
 59  \w   -109.00 -84.00   0.50    0.25    -- -102.00 -48.00 160.77   50
 60  \w   -119.00 -82.00   0.50    0.25    -- -102.00 -61.00   0.00   74
 61  \w   -117.00 -85.00   0.50    0.25    -- -102.00 -45.00  30.00   64
 62  \w   -127.00-101.00   0.50    0.25    -- -102.00 -55.00  26.45   52
 63  \w   -168.00-143.00   0.50    0.25    -- -102.00 -61.00   0.00   50
 64  \w   -102.00 -77.00   0.50    0.25    -- -102.00 -75.00-174.50   50
 65  \w    -59.00 -33.00   0.50    0.25    -- -102.00  -5.00-173.00   52
 66  \w    -68.00 -43.00   0.50    0.25    -- -102.00 115.00  13.97   50
 67  \w   -109.00 -78.00   0.50    0.25    -- -102.00 115.00  13.97   62
 68  \w   -172.00-147.00   0.50    0.25    -- -102.00   5.00   3.00   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      -0.0342607000
_diffrn_orient_matrix_UB_12      0.0005318000
_diffrn_orient_matrix_UB_13      -0.1190403000
_diffrn_orient_matrix_UB_21      0.1234629000
_diffrn_orient_matrix_UB_22      -0.0119063000
_diffrn_orient_matrix_UB_23      0.0003639000
_diffrn_orient_matrix_UB_31      -0.0090123000
_diffrn_orient_matrix_UB_32      -0.1655749000
_diffrn_orient_matrix_UB_33      -0.0003824000
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23956
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.548
_diffrn_reflns_theta_min         3.416
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56484
_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    1.182
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EA'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0577
_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^)+(0.1159P)^2^+0.0676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.1840
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4941
_reflns_number_total             5674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00840e2.cif
_cod_data_source_block           jhh-bingsuan-300k_auto
_cod_depositor_comments
'Adding full bibliography for 7132858--7132863.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132858
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H O F'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.3(4)
 -0.3(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(F3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F4) = Uanis(C7)
4. Others
 Fixed Sof: F7(0.5) F5(0.5) F3(0.5) F2(0.5) F1(0.5) F6(0.5) F10(0.5) F4(0.5)
 F39(0.5) F11(0.5)
5.a Ternary CH refined with riding coordinates:
 C006(H006), C00B(H00M), C00C(H00N), C00D(H00O), C00H(H00T), C00M(H00Z),
 C00U(H4)
5.b Secondary CH2 refined with riding coordinates:
 C001(H00A,H00B), C003(H00C,H00D), C005(H00E,H00F), C00F(H00P,H00Q), C00G(H00R,
 H00S), C00J(H00U,H00V), C00K(H00W,H00X), C00L(H00Y,H), C00O(H1,HC), C00S(H2,
 HD), C00T(H3,HE)
5.c Aromatic/amide H refined with riding coordinates:
 C002(H002)
5.d Idealised Me refined as rotating group:
 C007(H00G,H00H,H00I), C008(H00J,H00K,H00L), C00N(H00,HA,HB), C00W(H5,HF,HG),
 C010(H01A,H01B,H01C)
;
_shelx_res_checksum              63539
_shelx_hkl_checksum              98406
_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 1.895
_oxdiff_exptl_absorpt_empirical_full_min 0.533