Rethinking aromaticity of reduced thienoquinoids: insights from an S-Pechmann dye dianion
Shiokawa, Takumi; Fukazawa, Aiko; Chemical Communications 61 (2025) 10095–10098; doi:10.1039/D5CC02327K

data_7134619
_publ_section_title
;
 Rethinking aromaticity of reduced thienoquinoids: insights from an
 S-Pechmann dye dianion
;
_journal_issue                   55
_journal_name_full               'Chemical Communications'
_journal_page_first              10095
_journal_page_last               10098
_journal_paper_doi               10.1039/D5CC02327K
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C28 H30 S2'
_chemical_formula_sum            'C28 H30 S2'
_chemical_formula_weight         430.64
_chemical_melting_point          207.9(5)
_chemical_name_common            4
_chemical_name_systematic        5,5'-Bis(4-tert-butylphenyl)-3,3'-bithiophene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7205)
;
_audit_update_record
;
2025-04-25 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.958(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2850(8)
_cell_length_b                   6.0285(2)
_cell_length_c                   15.0211(6)
_cell_measurement_reflns_used    10397
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.4810
_cell_measurement_theta_min      1.6180
_cell_volume                     1156.66(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024) (IMPORT)'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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      0.00 180.00   1.00    1.00    --   30.00  45.00   0.00  180
  2  \w      0.00 180.00   1.00    1.00    --   30.00  45.00 -90.00  180
  3  \w      0.00 180.00   1.00    1.00    --   30.00  45.00-180.00  180
  4  \w      0.00 180.00   1.00    1.00    --   30.00  45.00-270.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0046747000
_diffrn_orient_matrix_UB_12      -0.0241354000
_diffrn_orient_matrix_UB_13      -0.0265204000
_diffrn_orient_matrix_UB_21      -0.0315384000
_diffrn_orient_matrix_UB_22      -0.0075652000
_diffrn_orient_matrix_UB_23      -0.0023189000
_diffrn_orient_matrix_UB_31      -0.0055110000
_diffrn_orient_matrix_UB_32      0.0636685000
_diffrn_orient_matrix_UB_33      -0.0103824000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.413
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        14.347
_diffrn_reflns_theta_max         15.553
_diffrn_reflns_theta_min         1.639
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.058
_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     139
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.4659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2347
_reflns_number_total             2647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02327k2.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '207.4-208.4' was changed
to '207.9(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134618--7134620.cif.
;
_cod_database_code               7134619
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.993
_diffrn_oxdiff_ac3_digest_hkl    01bf1ba6b24011d1a4e3873a9d2fc87d8d270b
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C8(H8), C6(H6), C9(H9), C7(H7)
1.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              58219
_shelx_hkl_checksum              33893
_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 4.212
_oxdiff_exptl_absorpt_empirical_full_min 0.386