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_1575419
_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         'C22 H12 S2, 0.667(C6 H5 Cl), 0.667(Cl O4)'
_chemical_formula_sum            'C26 H15.33 Cl1.33 O2.67 S2'
_chemical_formula_weight         481.77
_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                101.9045(16)
_cell_angle_beta                 107.3219(19)
_cell_angle_gamma                101.3854(16)
_cell_formula_units_Z            3
_cell_length_a                   10.5374(2)
_cell_length_b                   10.58339(18)
_cell_length_c                   15.8290(3)
_cell_measurement_reflns_used    15874
_cell_measurement_temperature    300
_cell_measurement_theta_max      76.9170
_cell_measurement_theta_min      3.0160
_cell_volume                     1584.41(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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 0.957
_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     35.00  92.00   0.50    0.20    --   47.91  57.00 120.00  114
  2  \w     27.00 120.00   0.50    0.20    --   47.91  77.00   0.00  186
  3  \w     27.00 120.00   0.50    0.20    --   47.91  77.00 -90.00  186
  4  \w     27.00 120.00   0.50    0.20    --   47.91  77.00-180.00  186
  5  \w     81.00 173.00   0.50    0.80    --  104.77 118.00 -82.00  184
  6  \w     54.00 120.00   0.50    0.20    --   47.91 158.00  71.00  132
  7  \w     54.00 160.00   0.50    0.80    --  104.77 158.00  71.00  212
  8  \w     76.00 174.00   0.50    0.80    --  104.77 125.00  30.00  196
  9  \w     97.00 175.00   0.50    0.80    --  104.77  37.00 -90.00  156
 10  \w     97.00 175.00   0.50    0.80    --  104.77  19.00-150.00  156
 11  \w     97.00 175.00   0.50    0.80    --  104.77  37.00   0.00  156
 12  \w    -24.00  24.00   0.50    0.20    --   47.91 -19.00 120.00   96
 13  \w    -24.00  24.00   0.50    0.20    --   47.91 -19.00  60.00   96
 14  \w    -24.00  24.00   0.50    0.20    --   47.91 -19.00 -60.00   96
 15  \w    -24.00  24.00   0.50    0.20    --   47.91 -19.00 -90.00   96
 16  \w     33.00  64.00   0.50    0.80    --  104.77 -57.00   0.00   62
 17  \w     33.00 105.00   0.50    0.80    --  104.77 -77.00-150.00  144
 18  \w     33.00  64.00   0.50    0.80    --  104.77 -57.00  30.00   62
 19  \w     33.00  64.00   0.50    0.80    --  104.77 -57.00 150.00   62
 20  \w     33.00 105.00   0.50    0.80    --  104.77 -77.00  60.00  144
 21  \w     35.00 106.00   0.50    0.80    --  104.77 -99.00  30.00  142
 22  \w     36.00 111.00   0.50    0.80    --  104.77-125.00  30.00  150
 23  \w     33.00 134.00   0.50    0.80    --  104.77-158.00  37.00  202
 24  \w     32.00 114.00   0.50    0.20    --   47.91-158.00  37.00  164
 25  \w     36.00 111.00   0.50    0.80    --  104.77-125.00-120.00  150
 26  \w     37.00 109.00   0.50    0.80    --  104.77-118.00-168.00  144
 27  \w     13.00  87.00   0.50    0.20    --   47.91-118.00-168.00  148
 28  \w    -28.00  26.00   0.50    0.20    --  -47.91  19.00 -60.00  108
 29  \w    -68.00 -25.00   0.50    0.80    --  -97.00  57.00 -90.00   86
 30  \w   -109.00 -25.00   0.50    0.80    --  -97.00  77.00 120.00  168
 31  \w    -68.00 -25.00   0.50    0.80    --  -97.00  57.00 120.00   86
 32  \w   -113.00 -38.00   0.50    0.20    --  -47.91 158.00  71.00  150
 33  \w   -134.00 -38.00   0.50    0.80    --  -97.00 158.00  71.00  192
 34  \w   -109.00 -29.00   0.50    0.80    --  -97.00 118.00 -82.00  160
 35  \w    -87.00 -19.00   0.50    0.20    --  -47.91 118.00 -82.00  136
 36  \w   -170.00 -89.00   0.50    0.80    --  -97.00 -19.00-120.00  162
 37  \w   -169.00 -89.00   0.50    0.80    --  -97.00 -37.00 -90.00  160
 38  \w    -64.50 -40.00   0.50    0.20    --  -47.91 -37.00 -60.00   49
;
_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      0.0893658000
_diffrn_orient_matrix_UB_12      -0.0087331000
_diffrn_orient_matrix_UB_13      -0.0611727000
_diffrn_orient_matrix_UB_21      -0.1313986000
_diffrn_orient_matrix_UB_22      -0.0708665000
_diffrn_orient_matrix_UB_23      -0.0857685000
_diffrn_orient_matrix_UB_31      -0.0123294000
_diffrn_orient_matrix_UB_32      0.1373778000
_diffrn_orient_matrix_UB_33      -0.0142016000
_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  0.0739
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31010
_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         77.651
_diffrn_reflns_theta_min         3.049
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.515
_exptl_crystal_description       needle
_exptl_crystal_F_000             742
_refine_diff_density_max         1.092
_refine_diff_density_min         -1.368
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6460
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0847
_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^)+(0.1375P)^2^+1.7129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2427
_refine_ls_wR_factor_ref         0.2568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5190
_reflns_number_total             6460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00680e2.cif
_cod_data_source_block           dntt-clo4-300k
_cod_depositor_comments
'Adding full bibliography for 1575411--1575428.cif.'
_cod_original_cell_volume        1584.40(6)
_cod_database_code               1575419
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O Cl S'
_chemical_oxdiff_usercomment     ' '
_diffrn_oxdiff_digest_hkl
;
0180f2bf1f778c106b9483486d6da4b41b90a4
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
O3 \\sim Cl37 \\sim O39 \\sim O40 \\sim O41 \\sim O42 \\sim O2 \\sim O5 \\sim
O1: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
1.7A
Uanis(O39) = Uanis(O41) = Uanis(O40) = Uanis(O42) = Uanis(Cl37)
3. Rigid body (RIGU) restrains
 O3, Cl37, O39, O40, O41, O42, O2, O5, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O39(0.5) O40(0.5) O41(0.5) O42(0.5) O2(0.5) O3(0.5) O5(0.5) O1(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C34(H34), C22(H22), C11(H11), C27(H27), C20(H20), C31(H31), C4(H4), C32(H32),
 C9(H9), C15(H15), C17(H17), C30(H30), C19(H19), C29(H29), C6(H6), C8(H8),
 C18(H18), C7(H7), C44(H44), C48(H48), C47(H47), C46(H46), C45(H45)
;
_shelx_res_checksum              16075
_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 2.086
_oxdiff_exptl_absorpt_empirical_full_min 0.558