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_7060727
_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         'C13 H14 O S4'
_chemical_formula_sum            'C13 H14 O S4'
_chemical_formula_weight         314.48
_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             2020-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-12 deposited with the CCDC.	2021-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5862(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.4907(2)
_cell_length_b                   5.32821(5)
_cell_length_c                   13.26611(11)
_cell_measurement_reflns_used    14713
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.9160
_cell_measurement_theta_min      2.1960
_cell_volume                     1423.73(2)
_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      100(2)
_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 0.996
_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     25.00 120.00   0.50    0.13    --   47.82  77.00-150.00  190
  2  \w     25.00 120.00   0.50    0.13    --   47.82  77.00 -90.00  190
  3  \w     25.00 120.00   0.50    0.13    --   47.82  77.00 -30.00  190
  4  \w     25.00 120.00   0.50    0.13    --   47.82  77.00  60.00  190
  5  \w     33.00 119.00   0.50    0.13    --   47.82  57.00  60.00  172
  6  \w     25.00 120.00   0.50    0.13    --   47.82  77.00 120.00  190
  7  \w     25.00 120.00   0.50    0.13    --   47.82  77.00 150.00  190
  8  \w     85.00 178.00   0.50    0.50    --  107.75  77.00 -90.00  186
  9  \w     85.00 178.00   0.50    0.50    --  107.75  77.00-120.00  186
 10  \w     91.00 178.00   0.50    0.50    --  107.75  61.00-180.00  174
 11  \w     95.00 178.00   0.50    0.50    --  107.75  45.00 -90.00  166
 12  \w     95.00 178.00   0.50    0.50    --  107.75  45.00 -60.00  166
 13  \w     95.00 178.00   0.50    0.50    --  107.75  30.00   0.00  166
 14  \w     95.00 178.00   0.50    0.50    --  107.75  30.00  30.00  166
 15  \w     85.00 178.00   0.50    0.50    --  107.75  77.00 150.00  186
 16  \w     95.00 135.00   0.50    0.50    --  107.75  45.00 120.00   80
 17  \w     94.00 178.00   0.50    0.50    --  107.75  15.00 -30.00  168
 18  \w    101.00 178.00   0.50    0.50    --  107.75  89.00-136.00  154
 19  \w     95.00 178.00   0.50    0.50    --  107.75 125.00-180.00  166
 20  \w     95.00 178.00   0.50    0.50    --  107.75 125.00 -60.00  166
 21  \w     95.00 178.00   0.50    0.50    --  107.75 125.00 -30.00  166
 22  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00 120.00   88
 23  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00 -30.00   88
 24  \w     35.00  79.00   0.50    0.50    --  107.75 -61.00 -90.00   88
 25  \w    -26.00  30.00   0.50    0.13    --   47.82 -19.00  90.00  112
 26  \w    -20.00  76.00   0.50    0.13    --   47.82 -89.00 107.00  192
 27  \w     35.00 112.00   0.50    0.50    --  107.75-125.00  90.00  154
 28  \w     35.00 112.00   0.50    0.50    --  107.75-125.00 -30.00  154
 29  \w     35.00 112.00   0.50    0.50    --  107.75-125.00 -90.00  154
 30  \w     35.00 112.00   0.50    0.50    --  107.75-125.00-150.00  154
 31  \w     35.00 108.00   0.50    0.50    --  107.75-109.00-144.78  146
 32  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00-150.00  142
 33  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00-120.00  142
 34  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 -90.00  142
 35  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00 -30.00  142
 36  \w     35.00 106.00   0.50    0.50    --  107.75 -94.00   0.00  142
 37  \w     35.00 106.00   0.50    0.50    --  107.75 -99.00 105.67  142
 38  \w     35.00 105.00   0.50    0.50    --  107.75 -89.00 107.00  140
 39  \w    -16.00  28.00   0.50    0.13    --  -47.82  19.00 -90.00   88
 40  \w    -16.00  28.00   0.50    0.13    --  -47.82  19.00 -30.00   88
 41  \w    -16.00  28.00   0.50    0.13    --  -47.82  19.00   0.00   88
 42  \w    -16.00  28.00   0.50    0.13    --  -47.82  19.00-150.00   88
 43  \w    -43.00 -14.00   0.50    0.50    --  -86.25  45.00-120.00   58
 44  \w    -79.00 -13.00   0.50    0.50    --  -86.25  89.00-136.00  132
 45  \w    -76.00  25.00   0.50    0.13    --  -47.82  89.00-136.00  202
 46  \w    -43.00 -14.00   0.50    0.50    --  -86.25  45.00 150.00   58
 47  \w   -159.00 -79.00   0.50    0.50    --  -86.25 -89.00 107.00  160
 48  \w   -119.00 -73.00   0.50    0.13    --  -47.82-125.00 -90.00   92
 49  \w   -119.00 -73.00   0.50    0.13    --  -47.82-125.00-180.00   92
;
_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      -0.0291390000
_diffrn_orient_matrix_UB_12      -0.2531569000
_diffrn_orient_matrix_UB_13      0.0261675000
_diffrn_orient_matrix_UB_21      -0.0662883000
_diffrn_orient_matrix_UB_22      0.0655162000
_diffrn_orient_matrix_UB_23      -0.0704723000
_diffrn_orient_matrix_UB_31      0.0246818000
_diffrn_orient_matrix_UB_32      -0.1233259000
_diffrn_orient_matrix_UB_33      -0.0911110000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33850
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.298
_diffrn_reflns_theta_min         2.193
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57499
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+1.0690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2744
_reflns_number_total             3010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02124a2.cif
_cod_data_source_block           metoxydtf
_cod_depositor_comments
'Adding full bibliography for 7060727--7060731.cif.'
_cod_database_code               7060727
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C13S4OH14
_shelx_estimated_absorpt_t_max   0.645
_shelx_estimated_absorpt_t_min   0.447
_diffrn_oxdiff_digest_frames
;
017d5c49f18452b5f89137c09e67e0246b00063c6bc
;
_diffrn_oxdiff_digest_hkl
;
01bafc30b317769138a6110c7b6aa250cc9b9f
;
_reflns_odcompleteness_completeness 100.00
_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), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              29739
_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 1.546
_oxdiff_exptl_absorpt_empirical_full_min 0.649