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_7251081
_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         'C19 H23 F5 S Si'
_chemical_formula_sum            'C19 H23 F5 S Si'
_chemical_formula_weight         406.52
_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             2025-05-16
_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                 94.529(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5617(3)
_cell_length_b                   19.8126(6)
_cell_length_c                   11.6723(4)
_cell_measurement_reflns_used    11967
_cell_measurement_temperature    153
_cell_measurement_theta_max      76.1360
_cell_measurement_theta_min      2.2930
_cell_volume                     1973.78(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.971
_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  76.00   0.50    0.05    --   48.52  77.00  60.00   96
  2  \w     41.00 122.00   0.50    0.05    --   48.52  27.00  -5.00  162
  3  \w     95.00 174.00   0.50    0.06    --  102.75  37.00  90.00  158
  4  \w     95.00 175.00   0.50    0.06    --  102.75  27.00  -5.00  160
  5  \w     31.00 106.00   0.50    0.06    --  102.75 -99.00  30.00  150
  6  \w    -23.00  41.00   0.50    0.05    --   48.52 -37.00  30.00  128
  7  \w     31.00 106.00   0.50    0.06    --  102.75 -99.00  60.00  150
  8  \w     31.00 111.00   0.50    0.06    --  102.75-125.00-180.00  160
  9  \w     31.00  69.00   0.50    0.06    --  102.75 -57.00-150.00   76
 10  \w    -24.00  28.00   0.50    0.05    --   48.52 -27.00-168.00  104
 11  \w    -24.00  18.00   0.50    0.05    --   48.52 -19.00  60.00   84
 12  \w    -24.00  25.00   0.50    0.05    --  -48.52  27.00  -5.00   98
 13  \w    -65.00 -30.00   0.50    0.06    -- -102.00  57.00  90.00   70
 14  \w    -65.00 -30.00   0.50    0.06    -- -102.00  57.00 120.00   70
 15  \w    -65.00 -30.00   0.50    0.06    -- -102.00  57.00 150.00   70
 16  \w    -65.00 -30.00   0.50    0.06    -- -102.00  57.00  60.00   70
 17  \w    -65.00 -30.00   0.50    0.06    -- -102.00  57.00 -60.00   70
 18  \w    -65.00 -30.00   0.50    0.06    -- -102.00  57.00 -90.00   70
 19  \w    -65.00 -30.00   0.50    0.06    -- -102.00  57.00-180.00   70
 20  \w   -121.00 -41.00   0.50    0.05    --  -48.52 -27.00-168.00  160
 21  \w   -175.00 -94.00   0.50    0.06    -- -102.00 -27.00-168.00  162
 22  \w   -174.00 -87.00   0.50    0.06    -- -102.00 -99.00 -30.00  174
 23  \w   -119.00 -74.00   0.50    0.05    --  -48.52-125.00 -90.00   90
 24  \w   -119.00 -74.00   0.50    0.05    --  -48.52-125.00 -30.00   90
;
_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      -0.0341345000
_diffrn_orient_matrix_UB_12      0.0013693000
_diffrn_orient_matrix_UB_13      -0.1315541000
_diffrn_orient_matrix_UB_21      0.1657667000
_diffrn_orient_matrix_UB_22      -0.0272973000
_diffrn_orient_matrix_UB_23      -0.0144931000
_diffrn_orient_matrix_UB_31      -0.0627659000
_diffrn_orient_matrix_UB_32      -0.0728103000
_diffrn_orient_matrix_UB_33      0.0027881000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1155
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18066
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.217
_diffrn_reflns_theta_min         4.407
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05888
_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    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_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         -0.736
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0723
_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^)+(0.1415P)^2^+0.9637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2104
_refine_ls_wR_factor_ref         0.2166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3632
_reflns_number_total             4013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00898k2.cif
_cod_data_source_block           yne-084-150k
_cod_depositor_comments
'Adding full bibliography for 7251080--7251083.cif.'
_cod_database_code               7251081
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H F S Si'
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.887
_diffrn_oxdiff_digest_frames
;
01fc342350d806e1146b1316f165a1347d0009615a8
;
_diffrn_oxdiff_digest_hkl
;
0111e57fb5460dee0fb074f4bec8402bbb6c90
;
_reflns_odcompleteness_completeness 99.92
_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 Ternary CH refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00I(H00I)
2.c Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00G), C00M(H00H,H00J,H00K), C00N(H00L,H00M,H00N), C00O(H00O,
 H00P,H00Q), C00P(H00R,H00S,H00T), C00Q(H00U,H00V,H00W)
;
_shelx_res_checksum              5750
_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 4.825
_oxdiff_exptl_absorpt_empirical_full_min 0.316