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_1575424
_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         '0.8(As F6), C22 H12 S2, 0.4(C6 H5 Cl)'
_chemical_formula_sum            'C24.4 H14 As0.8 Cl0.4 F4.8 S2'
_chemical_formula_weight         536.59
_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                69.962(2)
_cell_angle_beta                 85.719(2)
_cell_angle_gamma                78.822(2)
_cell_formula_units_Z            5
_cell_length_a                   13.6804(3)
_cell_length_b                   14.2592(4)
_cell_length_c                   14.8005(4)
_cell_measurement_reflns_used    14230
_cell_measurement_temperature    300
_cell_measurement_theta_max      74.1230
_cell_measurement_theta_min      3.2820
_cell_volume                     2660.82(12)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (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)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.957
_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   -104.00 -30.00   0.50    0.73    --  -40.28 139.00-140.00  148
  2  \w    -98.00 -26.00   0.50    0.73    --  -40.28 130.00  46.00  144
  3  \w     25.00 104.00   0.50    0.73    --   40.28-139.00 159.00  158
  4  \w     20.00  98.00   0.50    0.73    --   40.28-130.00 -26.00  156
  5  \w     67.00 114.00   0.50    0.73    --   40.28 139.00-140.00   94
  6  \w   -122.00 -30.00   0.50    2.90    --  -97.00 139.00-140.00  184
  7  \w   -115.00 -26.00   0.50    2.90    --  -97.00 130.00  46.00  178
  8  \w   -170.00 -79.00   0.50    2.90    --  -97.00-130.00 -26.00  182
  9  \w   -172.00 -73.00   0.50    2.90    --  -97.00-139.00 159.00  198
 10  \w     32.00 122.00   0.50    2.90    --  106.28-139.00 159.00  180
 11  \w     67.00 174.00   0.50    2.90    --  106.28 139.00-140.00  214
 12  \w     33.00 115.00   0.50    2.90    --  106.28-130.00 -26.00  164
 13  \w     73.00 175.00   0.50    2.90    --  106.28 130.00  46.00  204
 14  \w    -45.00  39.00   0.50    0.73    --  -40.28  37.00-150.00  168
 15  \w    -31.00  41.00   0.50    0.73    --  -40.28  19.00 -60.00  144
 16  \w    -31.00  41.00   0.50    0.73    --  -40.28  19.00-180.00  144
 17  \w    -33.00  63.00   0.50    0.73    --   40.28 -57.00  90.00  192
 18  \w      9.00 114.00   0.50    0.73    --   40.28  77.00-150.00  210
 19  \w    -53.00 -20.00   0.50    2.90    --  -97.00  45.00-150.00   66
 20  \w   -104.00 -22.00   0.50    2.90    --  -97.00  77.00  60.00  164
 21  \w    -53.00 -20.00   0.50    2.90    --  -97.00  45.00   0.00   66
 22  \w    -73.00 -22.00   0.50    2.90    --  -97.00  61.00 -90.00  102
 23  \w   -170.00 -82.00   0.50    2.90    --  -97.00-125.00 -60.00  176
 24  \w    -53.00 -20.00   0.50    2.90    --  -97.00  45.00  90.00   66
 25  \w   -171.00 -74.00   0.50    2.90    --  -97.00 -55.00-141.62  194
 26  \w   -173.00 -87.00   0.50    2.90    --  -97.00 -94.00-150.00  172
 27  \w    -53.00 -20.00   0.50    2.90    --  -97.00  45.00-180.00   66
 28  \w     32.00 100.00   0.50    2.90    --  106.28 -77.00-180.00  136
 29  \w     32.00  69.00   0.50    2.90    --  106.28 -61.00-120.00   74
 30  \w     32.00 100.00   0.50    2.90    --  106.28 -77.00-180.00  136
 31  \w     30.00 105.00   0.50    2.90    --  106.28 -94.00-180.00  150
 32  \w     32.00  69.00   0.50    2.90    --  106.28 -61.00-180.00   74
 33  \w     81.00 175.00   0.50    2.90    --  106.28  45.00 -90.00  188
 34  \w     81.00 175.00   0.50    2.90    --  106.28  45.00 -90.00  188
 35  \w     81.00 175.00   0.50    2.90    --  106.28  45.00  30.00  188
 36  \w     33.00 111.00   0.50    2.90    --  106.28-125.00  30.00  156
 37  \w     76.00 175.00   0.50    2.90    --  106.28 125.00 -90.00  198
 38  \w     33.00 111.00   0.50    2.90    --  106.28-125.00-180.00  156
 39  \w     32.00  69.00   0.50    2.90    --  106.28 -61.00 -60.00   74
 40  \w     81.00 146.00   0.50    2.90    --  106.28  45.00 -30.00  130
 41  \w     32.00  69.00   0.50    2.90    --  106.28 -61.00 -90.00   74
 42  \w     30.00 105.00   0.50    2.90    --  106.28 -94.00 -60.00  150
 43  \w     76.00 175.00   0.50    2.90    --  106.28 125.00-180.00  198
 44  \w     76.00 175.00   0.50    2.90    --  106.28 125.00-180.00  198
 45  \w     81.00 146.00   0.50    2.90    --  106.28  45.00 -30.00  130
 46  \w     52.00  78.00   0.50    2.90    --  106.28 -77.00 150.00   52
 47  \w     42.00  67.00   0.50    2.90    --  106.28 -61.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0187449000
_diffrn_orient_matrix_UB_12      -0.0405038000
_diffrn_orient_matrix_UB_13      0.1091315000
_diffrn_orient_matrix_UB_21      -0.1080864000
_diffrn_orient_matrix_UB_22      -0.0185375000
_diffrn_orient_matrix_UB_23      0.0187531000
_diffrn_orient_matrix_UB_31      0.0338154000
_diffrn_orient_matrix_UB_32      -0.1080832000
_diffrn_orient_matrix_UB_33      -0.0039123000
_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  0.0565
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            53481
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.228
_diffrn_reflns_theta_min         3.178
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.121a (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    1.674
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_refine_diff_density_max         1.218
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     768
_refine_ls_number_reflns         10516
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0779
_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^)+(0.0670P)^2^+8.5187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1991
_refine_ls_wR_factor_ref         0.2093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8284
_reflns_number_total             10516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00680e2.cif
_cod_data_source_block           dntt_asf6_300k
_cod_depositor_comments
'Adding full bibliography for 1575411--1575428.cif.'
_cod_original_formula_sum        'C24.40 H14 As0.80 Cl0.40 F4.80 S2'
_cod_database_code               1575424
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C244  H140  Cl4  F48  S20  As8  '
_diffrn_oxdiff_digest_hkl
;
432a6a65322eaf8b28309b3f5f7ec4bc37a31c
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 As1-F2H \\sim As1-F2I
 with sigma of 0.02
 As1-F2C \\sim As1-F2D
 with sigma of 0.02
 As-F8 \\sim As-F8A
 with sigma of 0.02
 As-F9 \\sim As-F9A
 with sigma of 0.02
3. Others
 Sof(F2I)=Sof(F2D)=1-FVAR(1)
 Sof(F2H)=Sof(F2C)=FVAR(1)
 Sof(F8A)=Sof(F9A)=1-FVAR(2)
 Sof(F8)=Sof(F9)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C12(H12), C17(H17), C1B(H1B), C1F(H1F), C1H(H1H), C1L(H1L),
 C1M(H1M), C1O(H1O), C1Q(H1Q), C1R(H1R), C1S(H1S), C1T(H1T), C1U(H1U), C1V(H1V),
  C1W(H1W), 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), C2B(H2B),
  C2F(H2F), C2G(H2G), C30(H30), C31(H31)
;
_shelx_res_checksum              19285
_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 1.775
_oxdiff_exptl_absorpt_empirical_full_min 0.726