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_1575428
_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                88.523(2)
_cell_angle_beta                 72.579(2)
_cell_angle_gamma                84.1070(10)
_cell_formula_units_Z            10
_cell_length_a                   14.9609(3)
_cell_length_b                   17.5144(2)
_cell_length_c                   21.7009(5)
_cell_measurement_reflns_used    35328
_cell_measurement_temperature    300
_cell_measurement_theta_max      76.2000
_cell_measurement_theta_min      3.0970
_cell_volume                     5396.74(19)
_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      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 0.949
_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   -120.00 -74.00   0.50    0.70    --  -47.91-137.00  66.00   92
  2  \w    -95.00 -26.00   0.50    0.70    --  -47.91 131.00 -47.00  138
  3  \w   -100.00 -29.00   0.50    0.70    --  -47.91 137.00 128.00  142
  4  \w     68.00 120.00   0.50    0.70    --   47.91 137.00 128.00  104
  5  \w     21.00  96.00   0.50    0.70    --   47.91-131.00-117.00  150
  6  \w     72.00 118.00   0.50    0.70    --   47.91 131.00 -47.00   92
  7  \w     24.00 100.00   0.50    0.70    --   47.91-137.00  66.00  152
  8  \w   -120.00 -29.00   0.50    2.50    --  -97.00 137.00 128.00  182
  9  \w   -120.00 -29.00   0.50    2.50    --  -97.00 137.00 128.00  182
 10  \w   -167.00 -78.00   0.50    2.50    --  -97.00-131.00-117.00  178
 11  \w   -116.00 -27.00   0.50    2.50    --  -97.00 131.00 -47.00  178
 12  \w     35.00 116.00   0.50    2.50    --  104.77-131.00-117.00  162
 13  \w     35.00 116.00   0.50    2.50    --  104.77-131.00-117.00  162
 14  \w     33.00 120.00   0.50    2.50    --  104.77-137.00  66.00  174
 15  \w     72.00 175.00   0.50    2.50    --  104.77 131.00 -47.00  206
 16  \w    -45.00  25.00   0.50    0.70    --  -47.91  37.00-120.00  140
 17  \w    -31.00  26.00   0.50    0.70    --  -47.91  19.00 -30.00  114
 18  \w    -24.00  27.00   0.50    0.70    --   47.91 -19.00 -30.00  102
 19  \w     27.00 120.00   0.50    0.70    --   47.91  77.00-120.00  186
 20  \w    -24.00  27.00   0.50    0.70    --   47.91 -19.00 -90.00  102
 21  \w   -169.00 -83.00   0.50    2.50    --  -97.00 -61.00 -94.51  172
 22  \w   -169.00 -81.00   0.50    2.50    --  -97.00 -64.00  -9.16  176
 23  \w   -169.00 -80.00   0.50    2.50    --  -97.00 -67.00 150.59  178
 24  \w   -169.00 -89.00   0.50    2.50    --  -97.00 -37.00 -60.00  160
 25  \w   -169.00 -81.00   0.50    2.50    --  -97.00 -66.00-109.51  176
 26  \w   -169.00 -74.00   0.50    2.50    --  -97.00-137.00  66.00  190
 27  \w    -68.00 -25.00   0.50    2.50    --  -97.00  57.00-180.00   86
 28  \w   -169.00 -80.00   0.50    2.50    --  -97.00 -67.00 150.59  178
 29  \w     35.00 106.00   0.50    2.50    --  104.77 -99.00  90.00  142
 30  \w     33.00 100.00   0.50    2.50    --  104.77 -77.00-150.00  134
 31  \w     35.00 107.00   0.50    2.50    --  104.77-102.00  68.09  144
 32  \w     97.00 175.00   0.50    2.50    --  104.77  37.00-120.00  156
 33  \w     97.00 175.00   0.50    2.50    --  104.77  37.00-120.00  156
 34  \w     33.00  63.00   0.50    2.50    --  104.77 -57.00  60.00   60
 35  \w     35.00 106.00   0.50    2.50    --  104.77 -99.00-120.00  142
 36  \w     33.00  63.00   0.50    2.50    --  104.77 -57.00   0.00   60
 37  \w     33.00 100.00   0.50    2.50    --  104.77 -77.00 -90.00  134
 38  \w     33.00  63.00   0.50    2.50    --  104.77 -57.00  90.00   60
 39  \w     36.00 111.00   0.50    2.50    --  104.77-125.00  90.00  150
 40  \w     33.00  63.00   0.50    2.50    --  104.77 -57.00  30.00   60
 41  \w     35.00 106.00   0.50    2.50    --  104.77 -99.00 -90.00  142
 42  \w     97.00 175.00   0.50    2.50    --  104.77  37.00 120.00  156
 43  \w     33.00 100.00   0.50    2.50    --  104.77 -77.00  90.00  134
 44  \w     68.00 175.00   0.50    2.50    --  104.77 137.00 128.00  214
 45  \w     27.00 120.00   0.50    0.70    --   47.91  77.00 120.00  186
 46  \w     27.00 120.00   0.50    0.70    --   47.91  77.00  30.00  186
;
_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      0.0982688000
_diffrn_orient_matrix_UB_12      -0.0115084000
_diffrn_orient_matrix_UB_13      0.0098667000
_diffrn_orient_matrix_UB_21      0.0457189000
_diffrn_orient_matrix_UB_22      -0.0040466000
_diffrn_orient_matrix_UB_23      -0.0737272000
_diffrn_orient_matrix_UB_31      0.0041227000
_diffrn_orient_matrix_UB_32      0.0875829000
_diffrn_orient_matrix_UB_33      -0.0017167000
_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  0.0638
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            126514
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.690
_diffrn_reflns_theta_min         2.134
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.938
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63992
_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    1.766
_exptl_crystal_description       block
_exptl_crystal_F_000             2832
_refine_diff_density_max         2.005
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1460
_refine_ls_number_reflns         21818
_refine_ls_number_restraints     240
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0848
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+19.6019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17406
_reflns_number_total             21818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00680e2.cif
_cod_data_source_block           dntt_sbf6_300k
_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               1575428
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S Cl F Sb'
_diffrn_oxdiff_ac3_digest_hkl    41ed537ea4ed7dfd9c97278987f6e2e7f4b0da
_diffrn_oxdiff_digest_hkl
;
43e6e2dda98c039ea0d08002d1c4ec8446b98a
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Sb21-F144 \\sim Sb21-F23
 with sigma of 0.02
 Sb21-F145 \\sim Sb21-F1A
 with sigma of 0.02
 Sb21-F8 \\sim Sb21-F8A
 with sigma of 0.02
 Sb21-F15 \\sim Sb21-F15A
 with sigma of 0.02
 C7-C3 \\sim C7-C12 \\sim C12-C10 \\sim C4-C10 \\sim C6-C4 \\sim C6-C3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F21 \\sim Sb21 \\sim F144 \\sim F145 \\sim F1 \\sim F8 \\sim F15 \\sim F23
\\sim F1A \\sim F8A \\sim F15A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
Uanis(C9) = Uanis(C2) = Uanis(C8)
4. Rigid body (RIGU) restrains
 F21, Sb21, F144, F145, F1, F8, F15, F23, F1A, F8A, F15A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F23)=Sof(F1A)=Sof(F8A)=Sof(F15A)=1-FVAR(1)
 Sof(F144)=Sof(F145)=Sof(F8)=Sof(F15)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C25(H25), C36(H36), C32(H32), C43(H43), C49(H49), C56(H56), C60(H60),
 C67(H67), C84(H84), C91(H91), C73(H73), C112(H112), C120(H120), C97(H97),
 C38(H38), C109(H109), C27(H27), C86(H86), C139(H139), C80(H80), C41(H41),
 C127(H127), C62(H62), C104(H104), C30(H30), C89(H89), C132(H132), C54(H54),
 C88(H88), C75(H75), C99(H99), C40(H40), C28(H28), C114(H114), C122(H122),
 C65(H65), C125(H125), C64(H64), C136(H136), C78(H78), C77(H77), C137(H137),
 C102(H102), C116(H116), C135(H135), C29(H29), C39(H39), C87(H87), C100(H100),
 C134(H134), C63(H63), C101(H101), C76(H76), C124(H124), C123(H123), C51(H51),
 C52(H52), C53(H53), C6(H6), C4(H4), C10(H10), C12(H12), C7(H7), C2(H2),
 C11(H11), C9(H9), C8(H8), C5(H5), C13(H13), C14(H14)
6.b Fitted hexagon refined as free rotating group:
 C3(C6,C4,C10,C12,C7), C1(C2,C11,C9,C8,C5)
;
_shelx_res_checksum              73042
_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 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.710