Donor/acceptor substituted dithiafulvenes and tetrathiafulvalene vinylogues: electronic absorption, crystallographic, and computational analyses
Afzali, Azadeh; Abdollahi, Maryam F.; Zhang, Baiyu; Zhao, Yuming; New Journal of Chemistry 45 (2021) 11918–11926; doi:10.1039/D1NJ02124A

data_7060729
_publ_section_title
;
 Donor/acceptor substituted dithiafulvenes and tetrathiafulvalene
 vinylogues: electronic absorption, crystallographic, and computational
 analyses
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11918
_journal_page_last               11926
_journal_paper_doi               10.1039/D1NJ02124A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C24 H20 N2 O4 S8'
_chemical_formula_sum            'C24 H20 N2 O4 S8'
_chemical_formula_weight         656.90
_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             2020-10-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                81.281(3)
_cell_angle_beta                 88.789(3)
_cell_angle_gamma                72.880(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0328(4)
_cell_length_b                   11.4799(6)
_cell_length_c                   12.7909(4)
_cell_measurement_reflns_used    7750
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.9090
_cell_measurement_theta_min      3.4530
_cell_volume                     1391.22(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.977
_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    -10.00  28.00   0.50    0.69    --  -46.95   7.00-100.00   76
  2  \w    -16.00  29.00   0.50    0.69    --  -46.95  19.00  30.00   90
  3  \w    -34.00  26.00   0.50    0.69    --  -46.95  37.00 -30.00  120
  4  \w    -34.00  26.00   0.50    0.69    --  -46.95  37.00  90.00  120
  5  \w      4.00 120.00   0.50    0.69    --   46.95   7.00-100.00  232
  6  \w     64.00 178.00   0.50    4.00    --  107.75   7.00-100.00  228
  7  \w     95.00 178.00   0.50    4.00    --  107.75  30.00-180.00  166
  8  \w     95.00 178.00   0.50    4.00    --  107.75  45.00-120.00  166
  9  \w     95.00 178.00   0.50    4.00    --  107.75  30.00 -60.00  166
 10  \w     94.00 178.00   0.50    4.00    --  107.75  15.00  90.00  168
 11  \w     95.00 178.00   0.50    4.00    --  107.75  30.00 150.00  166
 12  \w     95.00 178.00   0.50    4.00    --  107.75  45.00 120.00  166
 13  \w     92.00 178.00   0.50    4.00    --  107.75  60.00  99.77  172
 14  \w     34.00  95.00   0.50    0.69    --   46.95-125.00  30.00  122
 15  \w     35.00 106.00   0.50    4.00    --  107.75 -94.00  60.00  142
 16  \w     35.00  79.00   0.50    4.00    --  107.75 -61.00  30.00   88
 17  \w     35.00 107.00   0.50    4.00    --  107.75-105.00  17.89  144
 18  \w     35.00  79.00   0.50    4.00    --  107.75 -61.00-120.00   88
 19  \w     35.00  79.00   0.50    4.00    --  107.75 -61.00-180.00   88
 20  \w     35.00  79.00   0.50    4.00    --  107.75 -61.00-150.00   88
 21  \w     35.00 106.00   0.50    4.00    --  107.75 -94.00-180.00  142
 22  \w     34.00  95.00   0.50    0.69    --   46.95-125.00-150.00  122
 23  \w     35.00 112.00   0.50    4.00    --  107.75-125.00 -30.00  154
 24  \w     35.00 112.00   0.50    4.00    --  107.75-125.00   0.00  154
 25  \w     35.00 106.00   0.50    4.00    --  107.75 -94.00 120.00  142
 26  \w     35.00 106.00   0.50    4.00    --  107.75 -94.00 150.00  142
 27  \w     35.00 106.00   0.50    4.00    --  107.75 -94.00  90.00  142
 28  \w     35.00  79.00   0.50    4.00    --  107.75 -61.00  90.00   88
 29  \w     35.00 106.00   0.50    4.00    --  107.75 -94.00  30.00  142
 30  \w     35.00  79.00   0.50    4.00    --  107.75 -61.00 -90.00   88
 31  \w     35.00 106.00   0.50    4.00    --  107.75 -94.00-150.00  142
 32  \w     35.00 131.00   0.50    4.00    --  107.75 -77.00-180.00  192
 33  \w     35.00  79.00   0.50    4.00    --  107.75 -61.00   0.00   88
 34  \w     35.00 106.00   0.50    4.00    --  107.75 -94.00 -30.00  142
 35  \w     35.00 106.00   0.50    4.00    --  107.75 -94.00-120.00  142
 36  \w     35.00 107.00   0.50    4.00    --  107.75-102.00  25.84  144
 37  \w     35.00 112.00   0.50    4.00    --  107.75-125.00  90.00  154
 38  \w    -26.00  24.00   0.50    0.69    --   46.95  -7.00  84.00  100
 39  \w     24.00 119.00   0.50    0.69    --   46.95  77.00  30.00  190
 40  \w     24.00 119.00   0.50    0.69    --   46.95  77.00  90.00  190
 41  \w     24.00 119.00   0.50    0.69    --   46.95  77.00 -90.00  190
 42  \w     24.00 119.00   0.50    0.69    --   46.95  77.00-180.00  190
 43  \w     24.00 119.00   0.50    0.69    --   46.95  77.00-120.00  190
 44  \w     24.00 119.00   0.50    0.69    --   46.95  77.00 -30.00  190
 45  \w     24.00 119.00   0.50    0.69    --   46.95  77.00 150.00  190
 46  \w    -43.00 -14.00   0.50    4.00    --  -86.25  45.00-120.00   58
 47  \w    -43.00 -14.00   0.50    4.00    --  -86.25  45.00-180.00   58
 48  \w    -86.00 -13.00   0.50    0.69    --  -46.95 125.00 -30.00  146
 49  \w   -120.00 -25.00   0.50    0.69    --  -46.95  -7.00  84.00  190
 50  \w   -119.00 -73.00   0.50    0.69    --  -46.95-125.00  60.00   92
 51  \w   -120.00 -34.00   0.50    0.69    --  -46.95 -37.00 -30.00  172
 52  \w   -161.00 -65.00   0.50    4.00    --  -86.25  -7.00  84.00  192
;
_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      -0.1590894000
_diffrn_orient_matrix_UB_12      0.0255021000
_diffrn_orient_matrix_UB_13      -0.0104967000
_diffrn_orient_matrix_UB_21      -0.0207853000
_diffrn_orient_matrix_UB_22      0.1381544000
_diffrn_orient_matrix_UB_23      0.0014605000
_diffrn_orient_matrix_UB_31      0.0094921000
_diffrn_orient_matrix_UB_32      0.0211540000
_diffrn_orient_matrix_UB_33      -0.1214263000
_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  0.0530
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.303
_diffrn_reflns_theta_min         3.497
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.252
_exptl_absorpt_correction_T_max  0.37585
_exptl_absorpt_correction_T_min  0.30067
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       plate
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          0.067
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0643P)^2^+1.0722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4978
_reflns_number_total             5776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02124a2.cif
_cod_data_source_block           a7-dimerno2_red
_cod_depositor_comments
'Adding full bibliography for 7060727--7060731.cif.'
_cod_original_cell_volume        1391.22(10)
_cod_database_code               7060729
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C24H20N2O4S8
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              40036
_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 1.814
_oxdiff_exptl_absorpt_empirical_full_min 0.614