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_1575423
_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
_atom_sites_solution_primary     dual
_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                70.167(3)
_cell_angle_beta                 85.807(3)
_cell_angle_gamma                78.842(2)
_cell_formula_units_Z            5
_cell_length_a                   13.6803(4)
_cell_length_b                   14.0780(4)
_cell_length_c                   14.7274(5)
_cell_measurement_reflns_used    15553
_cell_measurement_temperature    200
_cell_measurement_theta_max      73.8170
_cell_measurement_theta_min      3.1560
_cell_volume                     2617.61(15)
_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)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.952
_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   -100.00 -28.00   0.50    0.35    --  -40.28 134.00  43.00  144
  2  \w   -101.00 -28.00   0.50    0.35    --  -40.28 135.00-136.00  146
  3  \w     23.00 102.00   0.50    0.35    --   40.28-135.00 157.00  158
  4  \w     22.00 100.00   0.50    0.35    --   40.28-134.00 -23.00  156
  5  \w   -118.00 -28.00   0.50    1.41    --  -97.00 134.00  43.00  180
  6  \w   -119.00 -28.00   0.50    1.41    --  -97.00 135.00-136.00  182
  7  \w   -170.00 -76.00   0.50    1.41    --  -97.00-134.00 -23.00  188
  8  \w   -172.00 -75.00   0.50    1.41    --  -97.00-135.00 157.00  194
  9  \w     32.00 119.00   0.50    1.41    --  106.28-135.00 157.00  174
 10  \w     70.00 175.00   0.50    1.41    --  106.28 135.00-136.00  210
 11  \w     70.00 175.00   0.50    1.41    --  106.28 134.00  43.00  210
 12  \w     34.00 118.00   0.50    1.41    --  106.28-134.00 -23.00  168
 13  \w    -31.00  41.00   0.50    0.35    --  -40.28  19.00-150.00  144
 14  \w    -31.00  41.00   0.50    0.35    --  -40.28  19.00 150.00  144
 15  \w   -114.00 -16.00   0.50    0.35    --  -40.28 -57.00-150.00  196
 16  \w      9.00 114.00   0.50    0.35    --   40.28  77.00  60.00  210
 17  \w    -41.00  27.00   0.50    0.35    --   40.28 -19.00-120.00  136
 18  \w   -112.00 -24.00   0.50    1.41    --  -97.00 125.00   0.00  176
 19  \w   -112.00 -24.00   0.50    1.41    --  -97.00 125.00 120.00  176
 20  \w   -172.00 -71.00   0.50    1.41    --  -97.00 -59.00-135.62  202
 21  \w    -53.00 -20.00   0.50    1.41    --  -97.00  45.00 -90.00   66
 22  \w   -172.00 -72.00   0.50    1.41    --  -97.00 -62.00 178.93  200
 23  \w    -53.00 -20.00   0.50    1.41    --  -97.00  45.00  30.00   66
 24  \w   -171.00 -73.00   0.50    1.41    --  -97.00 -54.00 -76.90  196
 25  \w   -173.00 -87.00   0.50    1.41    --  -97.00 -94.00  90.00  172
 26  \w    -53.00 -20.00   0.50    1.41    --  -97.00  45.00  60.00   66
 27  \w    -73.00 -22.00   0.50    1.41    --  -97.00  61.00 -90.00  102
 28  \w   -171.00 -73.00   0.50    1.41    --  -97.00 -54.00  40.50  196
 29  \w   -171.00 -73.00   0.50    1.41    --  -97.00 -54.00  40.50  196
 30  \w   -172.00 -72.00   0.50    1.41    --  -97.00 -62.00 178.93  200
 31  \w     76.00 175.00   0.50    1.41    --  106.28 125.00  90.00  198
 32  \w     33.00 111.00   0.50    1.41    --  106.28-125.00-150.00  156
 33  \w     32.00  69.00   0.50    1.41    --  106.28 -61.00 120.00   74
 34  \w     30.00 105.00   0.50    1.41    --  106.28 -94.00 -90.00  150
 35  \w     33.00 111.00   0.50    1.41    --  106.28-125.00  60.00  156
 36  \w     32.00 100.00   0.50    1.41    --  106.28 -77.00 120.00  136
 37  \w     81.00 175.00   0.50    1.41    --  106.28  45.00  90.00  188
 38  \w     33.00 111.00   0.50    1.41    --  106.28-125.00-120.00  156
 39  \w     72.00 110.00   0.50    1.41    --  106.28-125.00  90.00   76
 40  \w     81.00 134.00   0.50    1.41    --  106.28  61.00 120.00  106
 41  \w    146.00 172.00   0.50    1.41    --  106.28  61.00 120.00   52
 42  \w    123.00 173.00   0.50    1.41    --  106.28 125.00  90.00  100
 43  \w     34.00  90.00   0.50    1.41    --  106.28 -77.00 -30.00  112
 44  \w     36.00  69.00   0.50    1.41    --  106.28 -61.00-180.00   66
;
_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      0.0191286000
_diffrn_orient_matrix_UB_12      -0.0348346000
_diffrn_orient_matrix_UB_13      0.1092287000
_diffrn_orient_matrix_UB_21      -0.1079940000
_diffrn_orient_matrix_UB_22      -0.0185289000
_diffrn_orient_matrix_UB_23      0.0208071000
_diffrn_orient_matrix_UB_31      0.0338685000
_diffrn_orient_matrix_UB_32      -0.1114819000
_diffrn_orient_matrix_UB_33      0.0016080000
_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  0.0688
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            51703
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.584
_diffrn_reflns_theta_min         3.190
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86553
_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    1.702
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_refine_diff_density_max         1.850
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     785
_refine_ls_number_reflns         10211
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0432P)^2^+10.6872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8107
_reflns_number_total             10211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00680e2.cif
_cod_data_source_block           dntt_asf6_200k
_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               1575423
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C244  H140  Cl4  F48  S20  As8  '
_diffrn_oxdiff_digest_hkl
;
43e601cf39ad0bce8380fdb3c3ae8f253d1228
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 As1-F9 \\sim As1-F9A
 with sigma of 0.02
 As1-F5 \\sim As1-F5A
 with sigma of 0.02
 As1-F3 \\sim As1-F3A
 with sigma of 0.02
 As1-F7 \\sim As1-F7A
 with sigma of 0.02
 As1-F4 \\sim As1-F4A
 with sigma of 0.02
 As1-F8 \\sim As1-F8A
 with sigma of 0.02
3. Others
 Sof(F7A)=Sof(F4A)=Sof(F3A)=Sof(F8A)=Sof(F5A)=Sof(F9A)=1-FVAR(1)
 Sof(F9)=Sof(F5)=Sof(F3)=Sof(F7)=Sof(F4)=Sof(F8)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C49(H49), C38(H38), C55(H55), C27(H27), C31(H31), C20(H20), C62(H62),
 C23(H23), C42(H42), C60(H60), C25(H25), C44(H44), C57(H57), C36(H36), C33(H33),
  C67(H67), C59(H59), C72(H72), C22(H22), C45(H45), C74(H74), C24(H24),
 C58(H58), C34(H34), C47(H47), C35(H35), C69(H69), C71(H71), C46(H46), C70(H70),
  C78(H78), C81(H81), C82(H82), C79(H79), C80(H80)
;
_shelx_res_checksum              66819
_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 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.817