Synthesis, structure, and properties of twisted π-conjugated molecules featuring three-dimensional π-π interactions in solid states.
Nagase, Mai; Yoshida, Ryu; Nakano, Sachiko; Hirose, Takashi; Segawa, Yasutomo; Chemical communications (Cambridge, England) 61 (2025) 11187–11190; doi:10.1039/d5cc02387d

data_7134746
_publ_section_title
;
 Synthesis, structure, and properties of twisted &#x3c0;-conjugated
 molecules featuring three-dimensional &#x3c0;-&#x3c0; interactions in
 solid states.
;
_journal_issue                   60
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11187
_journal_page_last               11190
_journal_paper_doi               10.1039/d5cc02387d
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         '2(C12 H8 S2)'
_chemical_formula_sum            'C24 H16 S4'
_chemical_formula_weight         432.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-01-16 deposited with the CCDC.	2025-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.709(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0579(5)
_cell_length_b                   7.6145(3)
_cell_length_c                   21.3949(7)
_cell_measurement_reflns_used    5701
_cell_measurement_temperature    143.15
_cell_measurement_theta_max      28.7230
_cell_measurement_theta_min      3.2120
_cell_volume                     1891.00(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      143.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.812
_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    -45.00  18.00   0.50   20.00    --   -6.93  96.00 -88.00  126
  2  \w    -27.00  -2.00   0.50   20.00    --    8.33  96.00 -88.00   50
  3  \w    -29.00  60.00   0.50   20.00    --   -6.93  57.00-180.00  178
  4  \w    -14.00  15.00   0.50   20.00    --   -6.93 -57.00  60.00   58
  5  \w    -11.00  16.00   0.50   20.00    --    8.33 -96.00 162.00   54
  6  \w    -80.00 -17.00   0.50   20.00    --   -6.93 -57.00  60.00  126
  7  \w    -11.00  25.00   0.50   20.00    --   -6.93 -99.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0357698000
_diffrn_orient_matrix_UB_12      -0.0702011000
_diffrn_orient_matrix_UB_13      -0.0153980000
_diffrn_orient_matrix_UB_21      0.0494789000
_diffrn_orient_matrix_UB_22      -0.0517999000
_diffrn_orient_matrix_UB_23      0.0014776000
_diffrn_orient_matrix_UB_31      -0.0017310000
_diffrn_orient_matrix_UB_32      -0.0325840000
_diffrn_orient_matrix_UB_33      0.0307994000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.812
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16448
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.580
_diffrn_reflns_theta_min         2.675
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.626
_refine_diff_density_min         -1.222
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0843
_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^)+(0.0518P)^2^+13.3756P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3319
_reflns_number_total             4323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02387d3.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7134744--7134746.cif.'
_cod_database_code               7134746
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C5(H5), C6(H6), C17(H17)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              57829
_shelx_hkl_checksum              11160
_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 1.510
_oxdiff_exptl_absorpt_empirical_full_min 0.829