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_1575426
_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(F6 Sb), C22 H12 S2, 0.4(C6 H5 Cl)'
_chemical_formula_sum            'C24.4 H14 Cl0.4 F4.8 S2 Sb0.8'
_chemical_formula_weight         574.06
_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                89.627(2)
_cell_angle_beta                 73.391(2)
_cell_angle_gamma                84.665(2)
_cell_formula_units_Z            10
_cell_length_a                   14.7753(4)
_cell_length_b                   17.2538(4)
_cell_length_c                   21.4333(5)
_cell_measurement_reflns_used    41874
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.5090
_cell_measurement_theta_min      3.1320
_cell_volume                     5212.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.128a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.128a (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_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 0.944
_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    -68.00 -25.00   0.50    0.40    --  -97.00  57.00 -30.00   86
  2  \w   -104.00 -25.00   0.50    0.40    --  -97.00  77.00 150.00  158
  3  \w    -31.00  26.00   0.50    0.31    --  -47.91  19.00  60.00  114
  4  \w     27.00  67.00   0.50    0.31    --   47.91  77.00  60.00   80
  5  \w     97.00 175.00   0.50    0.40    --  104.77  37.00 120.00  156
  6  \w     35.00 120.00   0.50    0.31    --   47.91  57.00-120.00  170
  7  \w     35.00 106.00   0.50    0.40    --  104.77 -99.00-150.00  142
  8  \w     20.00  95.00   0.50    0.31    --   47.91-130.00-117.00  150
  9  \w     35.00 115.00   0.50    0.40    --  104.77-130.00-117.00  160
 10  \w     35.00 106.00   0.50    0.40    --  104.77 -99.00 -60.00  142
 11  \w     25.00 101.00   0.50    0.31    --   47.91-139.00  68.00  152
 12  \w     33.00 122.00   0.50    0.40    --  104.77-139.00  68.00  178
 13  \w     36.00 111.00   0.50    0.40    --  104.77-125.00 120.00  150
 14  \w     35.00 106.00   0.50    0.40    --  104.77 -99.00 120.00  142
 15  \w     36.00 108.00   0.50    0.40    --  104.77-107.00  95.77  144
 16  \w     35.00 106.00   0.50    0.40    --  104.77 -99.00 -90.00  142
 17  \w     33.00 100.00   0.50    0.40    --  104.77 -77.00-150.00  134
 18  \w     33.00  63.00   0.50    0.40    --  104.77 -57.00 -60.00   60
 19  \w     33.00  63.00   0.50    0.40    --  104.77 -57.00   0.00   60
 20  \w     33.00  63.00   0.50    0.40    --  104.77 -57.00 120.00   60
 21  \w     73.00 175.00   0.50    0.40    --  104.77 130.00 -45.00  204
 22  \w     67.00 174.00   0.50    0.40    --  104.77 139.00 128.00  214
 23  \w     67.00 174.00   0.50    0.40    --  104.77 139.00 128.00  214
 24  \w     67.00 120.00   0.50    0.31    --   47.91 139.00 128.00  106
 25  \w   -101.00 -30.00   0.50    0.31    --  -47.91 139.00 128.00  142
 26  \w   -121.00 -30.00   0.50    0.40    --  -97.00 139.00 128.00  182
 27  \w   -111.00 -28.00   0.50    0.40    --  -97.00 125.00   0.00  166
 28  \w   -115.00 -27.00   0.50    0.40    --  -97.00 130.00 -45.00  176
 29  \w    -95.00 -26.00   0.50    0.31    --  -47.91 130.00 -45.00  138
 30  \w   -167.00 -79.00   0.50    0.40    --  -97.00-130.00-117.00  176
 31  \w   -120.00 -27.00   0.50    0.31    --  -47.91 -77.00  30.00  186
 32  \w   -120.00 -27.00   0.50    0.31    --  -47.91 -77.00 -90.00  186
 33  \w   -169.00 -85.00   0.50    0.40    --  -97.00 -55.00 -94.12  168
 34  \w   -169.00 -76.00   0.50    0.40    --  -97.00 -77.00   0.00  186
 35  \w   -120.00 -73.00   0.50    0.31    --  -47.91-139.00  68.00   94
 36  \w   -169.00 -85.00   0.50    0.40    --  -97.00 -54.00 135.48  168
 37  \w   -169.00 -85.00   0.50    0.40    --  -97.00 -54.00 135.48  168
 38  \w   -169.00 -73.00   0.50    0.40    --  -97.00-139.00  68.00  192
 39  \w   -169.00 -89.00   0.50    0.40    --  -97.00 -37.00 -60.00  160
 40  \w   -169.00 -85.00   0.50    0.40    --  -97.00 -54.00-107.96  168
 41  \w   -170.00 -89.00   0.50    0.40    --  -97.00 -19.00-180.00  162
;
_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      0.0984955000
_diffrn_orient_matrix_UB_12      -0.0163350000
_diffrn_orient_matrix_UB_13      0.0110505000
_diffrn_orient_matrix_UB_21      0.0459757000
_diffrn_orient_matrix_UB_22      -0.0072159000
_diffrn_orient_matrix_UB_23      -0.0741651000
_diffrn_orient_matrix_UB_31      0.0114729000
_diffrn_orient_matrix_UB_32      0.0879010000
_diffrn_orient_matrix_UB_33      -0.0024249000
_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  0.0831
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            111765
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.957
_diffrn_reflns_theta_min         2.152
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.128a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_description       block
_exptl_crystal_F_000             2832
_refine_diff_density_max         1.979
_refine_diff_density_min         -2.122
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1497
_refine_ls_number_reflns         21035
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0650
_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^)+(0.0890P)^2^+33.4171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15334
_reflns_number_total             21035
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00680e2.cif
_cod_data_source_block           dntt_sbf6_100k
_cod_depositor_comments
'Adding full bibliography for 1575411--1575428.cif.'
_cod_original_formula_sum        'C24.40 H14 Cl0.40 F4.80 S2 Sb0.80'
_cod_database_code               1575426
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S Cl F Sb'
_diffrn_oxdiff_digest_hkl
;
430aa282bd052e89df7d253e1ec031727eefb9
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Sb22-F28 \\sim Sb22-F28A
 with sigma of 0.02
 Sb22-F25 \\sim Sb22-F25A
 with sigma of 0.02
 Sb22-F26 \\sim Sb22-F26A
 with sigma of 0.02
 Sb22-F27 \\sim Sb22-F27A
 with sigma of 0.02
3. Others
 Sof(F28A)=Sof(F25A)=1-FVAR(1)
 Sof(F28)=Sof(F25)=FVAR(1)
 Sof(F27A)=Sof(F26A)=1-FVAR(2)
 Sof(F26)=Sof(F27)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C50(H50), C39(H39), C104(H104), C45(H45), C80(H80), C67(H67), C32(H32),
 C126(H126), C48(H48), C91(H91), C61(H61), C43(H43), C115(H115), C98(H98),
 C74(H74), C133(H133), C37(H37), C128(H128), C69(H69), C87(H87), C72(H72),
 C111(H111), C109(H109), C142(H142), C34(H34), C35(H35), C139(H139), C122(H122),
  C96(H96), C47(H47), C106(H106), C82(H82), C36(H36), C56(H56), C63(H63),
 C71(H71), C58(H58), C117(H117), C93(H93), C129(H129), C144(H144), C108(H108),
 C130(H130), C60(H60), C146(H146), C70(H70), C131(H131), C107(H107), C46(H46),
 C59(H59), C143(H143), C94(H94), C120(H120), C118(H118), C119(H119), C85(H85),
 C95(H95), C141(H141), C83(H83), C84(H84), C150(H150), C161(H161), C154(H154),
 C159(H159), C157(H157), C160(H160), C158(H158), C153(H153), C151(H151),
 C152(H152)
;
_shelx_res_checksum              2444
_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.745