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_7060731
_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         'C12 H11 N O2 S4'
_chemical_formula_sum            'C12 H11 N O2 S4'
_chemical_formula_weight         329.46
_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             2020-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                82.169(2)
_cell_angle_beta                 89.492(2)
_cell_angle_gamma                73.337(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3968(3)
_cell_length_b                   8.3340(2)
_cell_length_c                   11.6041(3)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.2220
_cell_measurement_theta_min      3.8340
_cell_volume                     678.56(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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     24.00 120.00   0.50    0.05    --   47.70  80.00 133.00  192
  2  \w     84.00 178.00   0.50    0.50    --  107.75  80.00 133.00  188
  3  \w     95.00 178.00   0.50    0.50    --  107.75  30.00 150.00  166
  4  \w     91.00 178.00   0.50    0.50    --  107.75  61.00  90.00  174
  5  \w     94.00 178.00   0.50    0.50    --  107.75  15.00  60.00  168
  6  \w     85.00 178.00   0.50    0.50    --  107.75  77.00 -60.00  186
  7  \w     95.00 178.00   0.50    0.50    --  107.75  30.00 -90.00  166
  8  \w     94.00 178.00   0.50    0.50    --  107.75  15.00-120.00  168
  9  \w     95.00 178.00   0.50    0.50    --  107.75  30.00-180.00  166
 10  \w    -72.00  25.00   0.50    0.05    --  -47.70  80.00 133.00  194
 11  \w    -16.00  28.00   0.50    0.05    --  -47.70  19.00 120.00   88
 12  \w    -59.00  25.00   0.50    0.05    --  -47.70  57.00 -60.00  168
 13  \w    -16.00  28.00   0.50    0.05    --  -47.70  19.00-180.00   88
 14  \w    -43.00 -14.00   0.50    0.50    --  -86.25  45.00 -90.00   58
 15  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 -90.00  188
 16  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 -30.00  188
 17  \w   -119.00 -24.00   0.50    0.05    --  -47.70 -80.00   9.00  190
 18  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00  60.00  188
 19  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 150.00  188
 20  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00  90.00  188
 21  \w   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00  30.00  172
 22  \w   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00-180.00  172
 23  \w   -110.00 -13.00   0.50    0.50    --  -86.25  80.00 133.00  194
 24  \w   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00 150.00  172
 25  \w   -159.00 -66.00   0.50    0.50    --  -86.25 -70.00  53.67  186
 26  \w   -159.00 -62.00   0.50    0.50    --  -86.25 -80.00   9.00  194
 27  \w     34.00  95.00   0.50    0.05    --   47.70-125.00  30.00  122
 28  \w     35.00 112.00   0.50    0.50    --  107.75-125.00 -90.00  154
 29  \w     35.00 112.00   0.50    0.50    --  107.75-125.00 -30.00  154
 30  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 -60.00  142
 31  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00   0.00  142
 32  \w     35.00 107.00   0.50    0.50    --  107.75-105.00  74.74  144
 33  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 150.00  142
 34  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 120.00  142
 35  \w     35.00 112.00   0.50    0.50    --  107.75-125.00  60.00  154
 36  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00  60.00  142
 37  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 -30.00  142
 38  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 -90.00  142
 39  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00-180.00  142
 40  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00 -60.00   88
 41  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00  30.00   88
 42  \w     35.00 132.00   0.50    0.50    --  107.75 -80.00   9.00  194
 43  \w    -24.00  72.00   0.50    0.05    --   47.70 -80.00   9.00  192
 44  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00-120.00   88
 45  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00-180.00   88
 46  \w     95.00 178.00   0.50    0.50    --  107.75 125.00 -30.00  166
;
_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      -0.1902818000
_diffrn_orient_matrix_UB_12      -0.0226460000
_diffrn_orient_matrix_UB_13      -0.0358052000
_diffrn_orient_matrix_UB_21      0.0894462000
_diffrn_orient_matrix_UB_22      -0.0731489000
_diffrn_orient_matrix_UB_23      -0.1090037000
_diffrn_orient_matrix_UB_31      0.0557127000
_diffrn_orient_matrix_UB_32      -0.1791864000
_diffrn_orient_matrix_UB_33      0.0693750000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17088
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.214
_diffrn_reflns_theta_min         3.847
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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    1.612
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0491P)^2^+0.3644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2704
_reflns_number_total             2845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02124a2.cif
_cod_data_source_block           p-no2
_cod_depositor_comments
'Adding full bibliography for 7060727--7060731.cif.'
_cod_database_code               7060731
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H11NO2S4
_shelx_estimated_absorpt_t_max   0.740
_shelx_estimated_absorpt_t_min   0.539
_diffrn_oxdiff_digest_frames
;
01314e129e7144f2301018d3779676050000084fc4c
;
_diffrn_oxdiff_digest_hkl
;
01df64d896e894367ecfd2756aeb4a56e1073c
;
_reflns_odcompleteness_completeness 99.75
_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:
 C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              23153
_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 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.746