Radical cation salts of dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene: characteristic crystal structures and properties
Dhara, Barun; Bulgarevich, Kirill; Takimiya, Kazuo; CrystEngComm 27 (2025) 6333–6340; doi:10.1039/D5CE00680E

data_1575417
_publ_section_title
;
 Radical cation salts of
 dinaphtho[2,3-b:2&#x2032;,3&#x2032;-f]thieno[3,2-b]thiophene:
 characteristic crystal structures and properties
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              6333
_journal_page_last               6340
_journal_paper_doi               10.1039/D5CE00680E
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C6 H5 Br, 2.5(C22 H12 S2), 2(F6 P)'
_chemical_formula_sum            'C61 H35 Br F12 P2 S5'
_chemical_formula_weight         1298.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-02-17
_audit_creation_method
;
Olex2 1.5-ac7-012
(compiled 2024.11.06 svn.r97f918c9 for Rigaku Oxford Diffraction, GUI svn.r7082)
;
_audit_update_record
;
2025-07-06 deposited with the CCDC.	2025-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                70.7150(10)
_cell_angle_beta                 85.9760(10)
_cell_angle_gamma                79.0570(10)
_cell_formula_units_Z            2
_cell_length_a                   13.57690(10)
_cell_length_b                   14.0578(2)
_cell_length_c                   14.6788(2)
_cell_measurement_reflns_used    29471
_cell_measurement_temperature    200
_cell_measurement_theta_max      77.4930
_cell_measurement_theta_min      3.8140
_cell_volume                     2596.24(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac7-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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   -110.00 -37.00   0.50    0.30    --  -47.91 154.00   2.00  146
  2  \w    -89.00 -20.00   0.50    0.30    --  -47.91 120.00-155.00  138
  3  \w   -120.00 -62.00   0.50    0.30    --  -47.91-154.00 -36.00  116
  4  \w     56.00 120.00   0.50    0.30    --   47.91 154.00   2.00  128
  5  \w     15.00  89.00   0.50    0.30    --   47.91-120.00 120.00  148
  6  \w     31.00 111.00   0.50    0.30    --   47.91-154.00 -36.00  160
  7  \w   -109.00 -28.00   0.50    2.00    --  -97.00 120.00-155.00  162
  8  \w   -162.00 -62.00   0.50    2.00    --  -97.00-154.00 -36.00  200
  9  \w   -166.00 -85.00   0.50    2.00    --  -97.00-120.00 120.00  162
 10  \w   -132.00 -37.00   0.50    2.00    --  -97.00 154.00   2.00  190
 11  \w     37.00 109.00   0.50    2.00    --  106.00-120.00 120.00  144
 12  \w     80.00 175.00   0.50    2.00    --  106.00 120.00-155.00  190
 13  \w     34.00 132.00   0.50    2.00    --  106.00-154.00 -36.00  196
 14  \w     56.00 162.00   0.50    2.00    --  106.00 154.00   2.00  212
 15  \w    -31.00  26.00   0.50    0.30    --  -47.91  19.00-150.00  114
 16  \w    -31.00  26.00   0.50    0.30    --  -47.91  19.00-180.00  114
 17  \w    -31.00  26.00   0.50    0.30    --  -47.91  19.00  60.00  114
 18  \w    -45.00  25.00   0.50    0.30    --  -47.91  37.00 120.00  140
 19  \w    -24.00  27.00   0.50    0.30    --   47.91 -19.00 -30.00  102
 20  \w    -23.00  41.00   0.50    0.30    --   47.91 -37.00-150.00  128
 21  \w   -169.00 -85.00   0.50    2.00    --  -97.00 -54.00-169.66  168
 22  \w     37.00 112.00   0.50    2.00    --  106.00-125.00  90.00  150
 23  \w     34.00 100.00   0.50    2.00    --  106.00 -77.00 -30.00  132
 24  \w     34.00 100.00   0.50    2.00    --  106.00 -77.00 -90.00  132
 25  \w     34.00 106.00   0.50    2.00    --  106.00 -94.00 -30.00  144
 26  \w     37.00 112.00   0.50    2.00    --  106.00-125.00  30.00  150
 27  \w     98.00 175.00   0.50    2.00    --  106.00  15.00 -90.00  154
 28  \w     34.00 106.00   0.50    2.00    --  106.00 -94.00-120.00  144
 29  \w     37.00 112.00   0.50    2.00    --  106.00-125.00-150.00  150
 30  \w     37.00 112.00   0.50    2.00    --  106.00-125.00-150.00  150
 31  \w     97.00 175.00   0.50    2.00    --  106.00  45.00   0.00  156
 32  \w     76.00 175.00   0.50    2.00    --  106.00 125.00-180.00  198
 33  \w     34.00 106.00   0.50    2.00    --  106.00 -94.00 -60.00  144
 34  \w     34.00 100.00   0.50    2.00    --  106.00 -77.00  90.00  132
 35  \w     34.00 106.00   0.50    2.00    --  106.00 -94.00-180.00  144
 36  \w     34.00 100.00   0.50    2.00    --  106.00 -77.00-180.00  132
 37  \w     37.00 112.00   0.50    2.00    --  106.00-125.00 -90.00  150
 38  \w     98.00 175.00   0.50    2.00    --  106.00  15.00-180.00  154
 39  \w     34.00 106.00   0.50    2.00    --  106.00 -94.00 120.00  144
 40  \w     34.00 106.00   0.50    2.00    --  106.00 -94.00 120.00  144
 41  \w     98.00 175.00   0.50    2.00    --  106.00  30.00  60.00  154
 42  \w     34.00 106.00   0.50    2.00    --  106.00 -94.00 -90.00  144
 43  \w     34.00 100.00   0.50    2.00    --  106.00 -77.00  30.00  132
 44  \w     34.00 106.00   0.50    2.00    --  106.00 -94.00 150.00  144
 45  \w     76.00 175.00   0.50    2.00    --  106.00 125.00-180.00  198
 46  \w     34.00  69.00   0.50    2.00    --  106.00 -61.00-180.00   70
 47  \w     34.00 100.00   0.50    2.00    --  106.00 -77.00 -60.00  132
 48  \w     85.00 175.00   0.50    2.00    --  106.00  77.00  60.00  180
 49  \w     37.00 112.00   0.50    2.00    --  106.00-125.00  60.00  150
 50  \w     37.00 112.00   0.50    2.00    --  106.00-125.00  60.00  150
 51  \w     98.00 175.00   0.50    2.00    --  106.00  15.00-150.00  154
 52  \w     37.00 112.00   0.50    2.00    --  106.00-125.00 150.00  150
 53  \w     37.00 112.00   0.50    2.00    --  106.00-125.00 150.00  150
 54  \w     85.00 175.00   0.50    2.00    --  106.00  77.00 -60.00  180
 55  \w     98.00 175.00   0.50    2.00    --  106.00  15.00  60.00  154
 56  \w     34.00 100.00   0.50    2.00    --  106.00 -77.00-150.00  132
 57  \w     85.00 175.00   0.50    2.00    --  106.00  77.00  60.00  180
 58  \w     92.00 175.00   0.50    2.00    --  106.00  61.00 -30.00  166
 59  \w     92.00 175.00   0.50    2.00    --  106.00  61.00 -30.00  166
 60  \w     34.00 100.00   0.50    2.00    --  106.00 -77.00   0.00  132
 61  \w     76.00 175.00   0.50    2.00    --  106.00 125.00  90.00  198
 62  \w     76.00 175.00   0.50    2.00    --  106.00 125.00-120.00  198
 63  \w     98.00 175.00   0.50    2.00    --  106.00  15.00   0.00  154
 64  \w     76.00 175.00   0.50    2.00    --  106.00 125.00  30.00  198
 65  \w     76.00 175.00   0.50    2.00    --  106.00 125.00  30.00  198
 66  \w     34.00 106.00   0.50    2.00    --  106.00 -94.00  90.00  144
 67  \w     37.00 112.00   0.50    2.00    --  106.00-125.00-120.00  150
 68  \w     98.00 175.00   0.50    2.00    --  106.00  30.00-150.00  154
 69  \w     98.00 175.00   0.50    2.00    --  106.00  30.00   0.00  154
 70  \w     97.00 175.00   0.50    2.00    --  106.00  45.00 -90.00  156
 71  \w     97.00 175.00   0.50    2.00    --  106.00  45.00 -60.00  156
 72  \w     92.00 175.00   0.50    2.00    --  106.00  61.00-120.00  166
 73  \w     85.00 154.00   0.50    2.00    --  106.00  77.00  30.00  138
 74  \w    133.00 175.00   0.50    2.00    --  106.00  77.00  30.00   84
 75  \w     86.00 130.00   0.50    2.00    --  106.00  77.00 150.00   88
 76  \w    130.00 172.00   0.50    2.00    --  106.00 125.00 -60.00   84
 77  \w     39.00  64.00   0.50    2.00    --  106.00 -61.00 120.00   50
 78  \w    116.00 149.00   0.50    2.00    --  106.00  45.00 120.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20949
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.379
_diffrn_reflns_theta_min         3.190
_exptl_absorpt_coefficient_mu    4.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       needle
_exptl_crystal_F_000             1308
_refine_diff_density_max         1.790
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     731
_refine_ls_number_reflns         20949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0684
_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^)+(0.1217P)^2^+2.3257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1906
_refine_ls_wR_factor_ref         0.1990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17935
_reflns_number_total             20949
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9980\% 
around [-0.00 -0.00 1.00] (reciprocal) or [-0.01 -0.33 0.95] (direct)
;
_cod_data_source_file            d5ce00680e2.cif
_cod_data_source_block           dntt-pf6-bb-200k
_cod_depositor_comments
'Adding full bibliography for 1575411--1575428.cif.'
_cod_database_code               1575417
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S Br P F'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5681(11)
 0.4319(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C53(H53), C27(H27), C11(H11), C35(H35), C46(H46), C22(H22),
 C42(H42), C18(H18), C51(H51), C37(H37), C24(H24), C25(H25), C13(H13), C63(H63),
  C26(H26), C14(H14), C15(H15), C65(H65), C6(H6), C48(H48), C38(H38), C39(H39),
 C62(H62), C16(H16), C60(H60), C49(H49), C40(H40), C50(H50), C61(H61), C58(H58),
  C2(H2), C5(H5), C3(H3), C4(H4)
;
_shelx_res_checksum              53039
_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 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.732
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2