Studies of a bola-type bis(dithiafulvene) molecular system: synthesis, crystal structure, and electrochemical properties
Afzali, Azedeh; Tabasi, Zahra A.; Zhang, Baiyu H.; Zhao, Yuming; New Journal of Chemistry 46 (2022) 18133–18145; doi:10.1039/D2NJ01796B

data_7061735
_publ_section_title
;
 Studies of a bola-type bis(dithiafulvene) molecular system: synthesis,
 crystal structure, and electrochemical properties
;
_journal_issue                   38
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18133
_journal_page_last               18145
_journal_paper_doi               10.1039/D2NJ01796B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C22 H22 O3 S4'
_chemical_formula_sum            'C22 H22 O3 S4'
_chemical_formula_weight         462.63
_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             2022-05-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-10 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                93.6610(10)
_cell_angle_beta                 114.2170(10)
_cell_angle_gamma                113.636(2)
_cell_formula_units_Z            4
_cell_length_a                   12.7578(2)
_cell_length_b                   13.5031(2)
_cell_length_c                   15.2145(2)
_cell_measurement_reflns_used    33182
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3240
_cell_measurement_theta_min      3.6790
_cell_volume                     2106.48(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.974
_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     95.00 178.00   0.50   24.05    --  107.75 125.00 -30.00  166
  2  \w     95.00 178.00   0.50   24.05    --  107.75  45.00 -97.00  166
  3  \w     95.00 178.00   0.50   24.05    --  107.75  30.00-180.00  166
  4  \w     95.00 178.00   0.50   24.05    --  107.75  45.00-150.00  166
  5  \w     91.00 178.00   0.50   24.05    --  107.75  61.00  90.00  174
  6  \w     95.00 178.00   0.50   24.05    --  107.75 125.00 120.00  166
  7  \w     95.00 178.00   0.50   24.05    --  107.75  45.00 120.00  166
  8  \w     35.00 119.00   0.50    6.01    --   47.70  45.00 -97.00  168
  9  \w     35.00 106.00   0.50   24.05    --  107.75 -94.00   0.00  142
 10  \w     34.00  95.00   0.50    6.01    --   47.70-125.00 -30.00  122
 11  \w     35.00 112.00   0.50   24.05    --  107.75-125.00 -30.00  154
 12  \w     35.00 112.00   0.50   24.05    --  107.75-125.00  90.00  154
 13  \w     35.00 106.00   0.50   24.05    --  107.75 -94.00 150.00  142
 14  \w     35.00 112.00   0.50   24.05    --  107.75-125.00   0.00  154
 15  \w     35.00 106.00   0.50   24.05    --  107.75 -94.00  60.00  142
 16  \w     35.00 106.00   0.50   24.05    --  107.75 -98.00 -88.50  142
 17  \w     35.00 106.00   0.50   24.05    --  107.75 -94.00-180.00  142
 18  \w     35.00 106.00   0.50   24.05    --  107.75 -94.00-120.00  142
 19  \w     35.00 106.00   0.50   24.05    --  107.75 -94.00  90.00  142
 20  \w    -24.00  57.00   0.50    6.01    --   47.70 -45.00 112.00  162
 21  \w    -43.00  24.00   0.50    6.01    --  -47.70  45.00 -97.00  134
 22  \w    -43.00 -14.00   0.50   24.05    --  -86.25  45.00 -97.00   58
 23  \w    -86.00 -13.00   0.50    6.01    --  -47.70 125.00 -60.00  146
 24  \w    -43.00 -14.00   0.50   24.05    --  -86.25  45.00  60.00   58
 25  \w   -119.00 -35.00   0.50    6.01    --  -47.70 -45.00 112.00  168
 26  \w   -119.00 -73.00   0.50    6.01    --  -47.70-125.00  60.00   92
 27  \w   -119.00 -25.00   0.50    6.01    --  -47.70 -77.00  90.00  188
 28  \w   -119.00 -33.00   0.50    6.01    --  -47.70 -57.00 -60.00  172
 29  \w   -119.00 -25.00   0.50    6.01    --  -47.70 -77.00-150.00  188
 30  \w   -119.00 -59.00   0.50    6.01    --  -47.70 -77.00 -90.00  120
 31  \w   -119.00 -33.00   0.50    6.01    --  -47.70 -57.00   0.00  172
 32  \w   -158.00 -73.00   0.50   24.05    --  -86.25 -45.00 112.00  170
 33  \w     53.00  78.00   0.50    6.01    --   47.95  45.00 -97.00   50
 34  \w     71.00  96.00   0.50    6.01    --   47.95-125.00   0.00   50
 35  \w     35.00  72.00   0.50   24.05    --  107.75 -61.00   0.00   74
 36  \w     36.00  62.00   0.50   24.05    --  107.75 -94.00-150.00   52
 37  \w    116.00 142.00   0.50   24.05    --  107.75  77.00 -60.00   52
 38  \w    148.00 173.00   0.50   24.05    --  107.75  77.00 -60.00   50
 39  \w     56.00 106.00   0.50   24.05    --  107.75 -94.00 120.00  100
 40  \w     41.00  71.00   0.50   24.05    --  107.75 -61.00 -90.00   60
 41  \w     81.00 106.00   0.50   24.05    --  107.75 -94.00-150.00   50
 42  \w    100.00 125.00   0.50   24.05    --  107.75  61.00  60.00   50
 43  \w    135.00 173.00   0.50   24.05    --  107.75  61.00  60.00   76
 44  \w     70.00 106.00   0.50   24.05    --  107.75 -94.00 -30.00   72
 45  \w     90.00 116.00   0.50   24.05    --  107.75 -77.00-180.00   52
 46  \w    100.00 159.00   0.50   24.05    --  107.75  30.00  60.00  118
 47  \w     39.00  65.00   0.50   24.05    --  107.75-125.00  30.00   52
 48  \w     60.00  86.00   0.50   24.05    --  107.75-125.00 120.00   52
 49  \w     98.00 123.00   0.50   24.05    --  107.75  45.00-180.00   50
 50  \w    153.00 178.00   0.50   24.05    --  107.75  45.00-180.00   50
 51  \w     48.00  74.00   0.50   24.05    --  107.75 -61.00  90.00   52
 52  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00   0.00  190
 53  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00 150.00  190
 54  \w   -120.00 -73.00   0.50    6.01    --  -47.95-125.00   0.00   94
 55  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00  60.00  190
 56  \w   -121.00 -35.00   0.50    6.01    --  -47.95 -37.00-150.00  172
 57  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00 -30.00  190
 58  \w   -121.00 -51.00   0.50    6.01    --  -47.95 -37.00  30.00  140
 59  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00 -90.00  190
 60  \w     -8.00  17.00   0.50    6.01    --   47.95 -45.00 112.00   50
 61  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00 -60.00  190
 62  \w   -119.00 -33.00   0.50    6.01    --  -47.95 -58.00 -47.33  172
 63  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00-180.00  190
 64  \w   -119.00 -33.00   0.50    6.01    --  -47.95 -57.00-120.00  172
 65  \w   -120.00 -30.00   0.50    6.01    --  -47.95 -64.00 156.95  180
 66  \w   -119.00 -33.00   0.50    6.01    --  -47.95 -57.00 120.00  172
 67  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00  30.00  190
 68  \w   -121.00 -35.00   0.50    6.01    --  -47.95 -37.00 -30.00  172
 69  \w   -122.00 -35.00   0.50    6.01    --  -47.95 -19.00 -30.00  174
 70  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00 120.00  190
 71  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00-150.00  190
 72  \w   -121.00 -35.00   0.50    6.01    --  -47.95 -37.00 150.00  172
 73  \w   -120.00 -25.00   0.50    6.01    --  -47.95 -77.00-120.00  190
 74  \w     33.00 119.00   0.50    6.01    --   47.95  57.00-120.00  172
 75  \w     36.00 121.00   0.50    6.01    --   47.95  37.00 -30.00  170
 76  \w     33.00 119.00   0.50    6.01    --   47.95  57.00 120.00  172
 77  \w    -24.00 120.00   0.50    6.01    --   47.95   0.00 -60.00  288
 78  \w     35.00 122.00   0.50    6.01    --   47.95  19.00 -90.00  174
 79  \w    -24.00 120.00   0.50    6.01    --   47.95   0.00-120.00  288
 80  \w     33.00 119.00   0.50    6.01    --   47.95  57.00   0.00  172
 81  \w    -24.00 120.00   0.50    6.01    --   47.95   0.00-150.00  288
 82  \w    -24.00 120.00   0.50    6.01    --   47.95   0.00 -90.00  288
 83  \w    -24.00  58.00   0.50    6.01    --   47.95   0.00-180.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0618772000
_diffrn_orient_matrix_UB_12      0.0152507000
_diffrn_orient_matrix_UB_13      0.0646293000
_diffrn_orient_matrix_UB_21      -0.0356289000
_diffrn_orient_matrix_UB_22      -0.1209648000
_diffrn_orient_matrix_UB_23      0.0086734000
_diffrn_orient_matrix_UB_31      0.1318463000
_diffrn_orient_matrix_UB_32      0.0435512000
_diffrn_orient_matrix_UB_33      0.0952048000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20864
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.565
_diffrn_reflns_theta_min         3.311
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.327
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.459
_exptl_crystal_description       irregular
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.917
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         20864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0769
_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^)+(0.1460P)^2^+3.6784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2380
_refine_ls_wR_factor_ref         0.2536
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15742
_reflns_number_total             20864
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.0235\% 
around [0.02 0.02 1.00] (reciprocal) or [0.52 0.28 0.81] (direct)
Component 3 rotated by 1.1688\% 
around [0.78 -0.38 -0.49] (reciprocal) or [0.98 -0.12 -0.16] (direct)
;
_cod_data_source_file            d2nj01796b2.cif
_cod_data_source_block           a21c1_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7061734--7061735.cif.'
_cod_original_cell_volume        2106.47(6)
_cod_database_code               7061735
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C22H22O3S4
_shelx_estimated_absorpt_t_max   0.819
_shelx_estimated_absorpt_t_min   0.616
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.511(4)
 0.1703(9) 0.319(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C35(H35A,H35B), C36(H36A,
 H36B), C37(H37A,H37B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C17(H17), C18(H18), C20(H20),
 C21(H21), C22(H22), C28(H28), C30(H30), C31(H31), C33(H33), C34(H34), C39(H39),
  C40(H40), C42(H42), C43(H43), C44(H44)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              84486
_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 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.517
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               3