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_1575414
_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         '0.4(C6 H5 Br), C22 H12 S2, 0.8(F6 P)'
_chemical_formula_sum            'C24.4 H14 Br0.4 F4.8 P0.8 S2'
_chemical_formula_weight         519.22
_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                70.481(3)
_cell_angle_beta                 86.305(2)
_cell_angle_gamma                79.140(2)
_cell_formula_units_Z            5
_cell_length_a                   13.6133(3)
_cell_length_b                   14.2244(3)
_cell_length_c                   14.7406(5)
_cell_measurement_reflns_used    23024
_cell_measurement_temperature    300
_cell_measurement_theta_max      77.0820
_cell_measurement_theta_min      3.1520
_cell_volume                     2642.16(13)
_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      300.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_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   -118.00 -64.00   0.50    0.50    --  -47.66-151.00 -39.00  108
  2  \w    -89.00 -21.00   0.50    0.50    --  -47.66 121.00-156.00  136
  3  \w   -108.00 -35.00   0.50    0.50    --  -47.66 151.00   3.00  146
  4  \w     59.00 119.00   0.50    0.50    --   47.66 151.00   3.00  120
  5  \w     15.00  89.00   0.50    0.50    --   47.66-121.00 120.00  148
  6  \w   -165.00 -64.00   0.50    1.50    --  -97.00-151.00 -39.00  202
  7  \w   -109.00 -28.00   0.50    1.50    --  -97.00 121.00-156.00  162
  8  \w   -129.00 -35.00   0.50    1.50    --  -97.00 151.00   3.00  188
  9  \w   -166.00 -85.00   0.50    1.50    --  -97.00-121.00 120.00  162
 10  \w     79.00 175.00   0.50    1.50    --  106.00 121.00-156.00  192
 11  \w     34.00 130.00   0.50    1.50    --  106.00-151.00 -39.00  192
 12  \w     59.00 165.00   0.50    1.50    --  106.00 151.00   3.00  212
 13  \w     37.00 110.00   0.50    1.50    --  106.00-121.00 120.00  146
 14  \w     37.00 110.00   0.50    1.50    --  106.00-121.00 120.00  146
 15  \w   -118.00 -27.00   0.50    0.50    --  -47.66 -77.00  90.00  182
 16  \w    -31.00  26.00   0.50    0.50    --  -47.66  19.00  30.00  114
 17  \w   -118.00 -27.00   0.50    0.50    --  -47.66 -77.00 150.00  182
 18  \w    -31.00  26.00   0.50    0.50    --  -47.66  19.00 120.00  114
 19  \w     30.00 109.00   0.50    0.50    --   47.66-151.00 -39.00  158
 20  \w   -169.00 -85.00   0.50    1.50    --  -97.00 -53.00-170.32  168
 21  \w    -53.00 -25.00   0.50    1.50    --  -97.00  45.00 -30.00   56
 22  \w     34.00 100.00   0.50    1.50    --  106.00 -77.00 -90.00  132
 23  \w     34.00 100.00   0.50    1.50    --  106.00 -77.00 120.00  132
 24  \w     34.00  69.00   0.50    1.50    --  106.00 -61.00 -30.00   70
 25  \w     34.00 100.00   0.50    1.50    --  106.00 -77.00-180.00  132
 26  \w     34.00 100.00   0.50    1.50    --  106.00 -77.00 150.00  132
 27  \w     98.00 175.00   0.50    1.50    --  106.00  30.00  90.00  154
 28  \w     98.00 175.00   0.50    1.50    --  106.00  30.00  90.00  154
 29  \w     34.00  69.00   0.50    1.50    --  106.00 -61.00-180.00   70
 30  \w     34.00 106.00   0.50    1.50    --  106.00 -94.00 -30.00  144
 31  \w     97.00 175.00   0.50    1.50    --  106.00  45.00 120.00  156
 32  \w     37.00 112.00   0.50    1.50    --  106.00-125.00 -30.00  150
 33  \w     37.00 112.00   0.50    1.50    --  106.00-125.00 150.00  150
 34  \w     34.00  69.00   0.50    1.50    --  106.00 -61.00-150.00   70
 35  \w     98.00 175.00   0.50    1.50    --  106.00  30.00 -60.00  154
 36  \w     37.00 112.00   0.50    1.50    --  106.00-125.00  90.00  150
 37  \w     98.00 175.00   0.50    1.50    --  106.00  30.00-150.00  154
 38  \w     34.00 100.00   0.50    1.50    --  106.00 -77.00-180.00  132
 39  \w     98.00 175.00   0.50    1.50    --  106.00  30.00-120.00  154
 40  \w     37.00 112.00   0.50    1.50    --  106.00-125.00 -30.00  150
 41  \w     37.00 112.00   0.50    1.50    --  106.00-125.00-150.00  150
 42  \w     37.00 112.00   0.50    1.50    --  106.00-125.00-150.00  150
 43  \w     37.00 112.00   0.50    1.50    --  106.00-125.00  60.00  150
 44  \w     37.00 112.00   0.50    1.50    --  106.00-125.00  60.00  150
 45  \w     37.00 112.00   0.50    1.50    --  106.00-125.00  30.00  150
 46  \w     92.00 175.00   0.50    1.50    --  106.00  61.00  90.00  166
 47  \w     34.00 100.00   0.50    1.50    --  106.00 -77.00   0.00  132
 48  \w     37.00 112.00   0.50    1.50    --  106.00-125.00-180.00  150
 49  \w     34.00 106.00   0.50    1.50    --  106.00 -94.00 -90.00  144
 50  \w     98.00 175.00   0.50    1.50    --  106.00  30.00-180.00  154
 51  \w     34.00 100.00   0.50    1.50    --  106.00 -77.00  30.00  132
 52  \w     34.00 100.00   0.50    1.50    --  106.00 -77.00-150.00  132
 53  \w     98.00 175.00   0.50    1.50    --  106.00  30.00 -30.00  154
 54  \w     76.00 153.00   0.50    1.50    --  106.00 125.00  90.00  154
;
_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     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.141
_diffrn_reflns_theta_min         3.306
_exptl_absorpt_coefficient_mu    4.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57565
_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    1.632
_exptl_crystal_description       needle
_exptl_crystal_F_000             1308
_refine_diff_density_max         1.685
_refine_diff_density_min         -1.086
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     731
_refine_ls_number_reflns         20995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0859
_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^)+(0.1749P)^2^+0.4261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2478
_refine_ls_wR_factor_ref         0.2778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13761
_reflns_number_total             20995
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9874\% 
around [-0.00 -0.00 1.00] (reciprocal) or [-0.00 -0.33 0.94] (direct)
;
_cod_data_source_file            d5ce00680e2.cif
_cod_data_source_block           dntt-pf6-bb-300k
_cod_depositor_comments
'Adding full bibliography for 1575411--1575428.cif.'
_cod_original_formula_sum        'C24.40 H14 Br0.40 F4.80 P0.80 S2'
_cod_database_code               1575414
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S Br P F'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5676(15)
 0.4324(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C1B(H1B), C1C(H1C), C1E(H1E), C1G(H1G), C1H(H1H), C1J(H1J),
 C1M(H1M), C1N(H1N), C1O(H1O), C1P(H1P), C1Q(H1Q), C1V(H1V), C1X(H1X), C1Y(H1Y),
  C1Z(H1Z), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29), C2A(H2A), C2B(H2B), C2C(H2C), C2D(H2D),
  C2E(H2E), C2G(H2G), C2H(H2H), C2I(H2I), C2J(H2J)
;
_shelx_res_checksum              9422
_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 1.936
_oxdiff_exptl_absorpt_empirical_full_min 0.623
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2