Systematic investigation of the effect of trialkylsilyl groups on the crystal structures of perfluorophenyl-substituted thiophene
Yonezawa, Takeharu; Ito, Hajime; Jin, Mingoo; CrystEngComm 28 (2026) 390–395; doi:10.1039/D5CE00898K

data_7251082
_publ_section_title
;
 Systematic investigation of the effect of trialkylsilyl groups on the
 crystal structures of perfluorophenyl-substituted thiophene
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              390
_journal_page_last               395
_journal_paper_doi               10.1039/D5CE00898K
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C13 H11 F5 S Si'
_chemical_formula_sum            'C13 H11 F5 S Si'
_chemical_formula_weight         322.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-09-12 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.7633(3)
_cell_length_b                   6.85410(10)
_cell_length_c                   13.4097(2)
_cell_measurement_reflns_used    17953
_cell_measurement_temperature    153
_cell_measurement_theta_max      75.9900
_cell_measurement_theta_min      2.8480
_cell_volume                     2827.50(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      153
_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 0.984
_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    -24.00  31.00   0.50    0.05    --   48.77 -29.00 -61.00  110
  2  \w    -24.00  18.00   0.50    0.05    --   48.77 -19.00-120.00   84
  3  \w     31.00  69.00   0.50    0.10    --  102.75 -57.00 -60.00   76
  4  \w     31.00  69.00   0.50    0.10    --  102.75 -57.00 -90.00   76
  5  \w     31.00  69.00   0.50    0.10    --  102.75 -57.00  60.00   76
  6  \w     31.00  69.00   0.50    0.10    --  102.75 -57.00  90.00   76
  7  \w     31.00  69.00   0.50    0.10    --  102.75 -57.00 150.00   76
  8  \w     31.00 106.00   0.50    0.10    --  102.75 -99.00  90.00  150
  9  \w     31.00 111.00   0.50    0.10    --  102.75-125.00  90.00  160
 10  \w    -22.00  78.00   0.50    0.05    --   48.77 -95.00 124.00  200
 11  \w    -14.00  25.00   0.50    0.05    --  -48.77  19.00 -30.00   78
 12  \w    -65.00 -30.00   0.50    0.10    -- -102.00  57.00-150.00   70
 13  \w   -109.00 -30.00   0.50    0.10    -- -102.00 120.00 -45.00  158
 14  \w   -105.00 -30.00   0.50    0.10    -- -102.00  95.00-125.00  150
 15  \w   -174.00 -94.00   0.50    0.10    -- -102.00 -29.00 -61.00  160
 16  \w   -174.00 -81.00   0.50    0.10    -- -102.00 -77.00-120.00  186
 17  \w   -174.00 -94.00   0.50    0.10    -- -102.00 -37.00 150.00  160
 18  \w     28.00 121.00   0.50    0.05    --   48.77  77.00-150.00  186
 19  \w     28.00  91.00   0.50    0.05    --   48.77  77.00 -60.00  126
 20  \w     36.00 121.00   0.50    0.05    --   48.77  57.00  30.00  170
;
_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      -0.2095337000
_diffrn_orient_matrix_UB_12      -0.0412644000
_diffrn_orient_matrix_UB_13      -0.0018736000
_diffrn_orient_matrix_UB_21      0.0013727000
_diffrn_orient_matrix_UB_22      -0.0141452000
_diffrn_orient_matrix_UB_23      0.0497073000
_diffrn_orient_matrix_UB_31      -0.0811515000
_diffrn_orient_matrix_UB_32      0.1063088000
_diffrn_orient_matrix_UB_33      0.0058042000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25659
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.299
_diffrn_reflns_theta_min         2.873
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 2068 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5340
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0498P)^2^+0.6078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                5113
_reflns_number_total             5340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00898k2.cif
_cod_data_source_block           yne-132-full-150k
_cod_depositor_comments
'Adding full bibliography for 7251080--7251083.cif.'
_cod_database_code               7251082
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H Si F S'
_shelx_estimated_absorpt_t_max   0.853
_shelx_estimated_absorpt_t_min   0.853
_diffrn_oxdiff_digest_frames
;
0172067ebf16a5cb12beaf25b6364887f600096e4c9
;
_diffrn_oxdiff_digest_hkl
;
01242e161eacd38f9c34f700efde9e53fcac9d
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00M(H00M), C00S(H00S)
2.b Idealised Me refined as rotating group:
 C00Y(H00A,H00B,H00C), C010(H01G,H01H,H01I), C011(H01J,H01K,H01L), C012(H01A,
 H01B,H01C), C013(H01D,H01E,H01F), C014(H01M,H01N,H01O)
;
_shelx_res_checksum              6361
_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 1.607
_oxdiff_exptl_absorpt_empirical_full_min 0.638