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_7060730
_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 H22 N2 O4 S9, 0.75 (C H2 Cl2)'
_chemical_formula_sum            'C24.75 H23.5 Cl1.5 N2 O4 S9'
_chemical_formula_weight         754.67
_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             2020-10-13
_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                90
_cell_angle_beta                 97.1341(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.54193(13)
_cell_length_b                   14.0748(3)
_cell_length_c                   27.4895(5)
_cell_measurement_reflns_used    12752
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2840
_cell_measurement_theta_min      3.2470
_cell_volume                     3279.37(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 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    -53.00  25.00   0.50    0.53    --  -47.95  53.00  13.00  156
  2  \w    -16.00  28.00   0.50    0.53    --  -47.95  19.00   0.00   88
  3  \w    -53.00 -14.00   0.50    2.11    --  -86.25  53.00  13.00   78
  4  \w    -43.00 -14.00   0.50    2.11    --  -86.25  45.00 150.00   58
  5  \w     34.00 119.00   0.50    0.53    --   47.95  53.00  13.00  170
  6  \w     94.00 178.00   0.50    2.11    --  107.75  53.00  13.00  168
  7  \w     95.00 178.00   0.50    2.11    --  107.75  45.00 -60.00  166
  8  \w    153.00 178.00   0.50    2.11    --  107.75   0.00-150.00   50
  9  \w    114.00 147.00   0.50    2.11    --  107.75   0.00-150.00   66
 10  \w     95.00 178.00   0.50    2.11    --  107.75  45.00 -90.00  166
 11  \w     95.00 178.00   0.50    2.11    --  107.75  45.00-120.00  166
 12  \w     91.00 178.00   0.50    2.11    --  107.75  61.00 -30.00  174
 13  \w     95.00 178.00   0.50    2.11    --  107.75  45.00  60.00  166
 14  \w     85.00 178.00   0.50    2.11    --  107.75  77.00  90.00  186
 15  \w     47.00  73.00   0.50    2.11    --  107.75   0.00-150.00   52
 16  \w     35.00  67.00   0.50    2.11    --  107.75 -53.00-131.00   64
 17  \w     35.00 106.00   0.50    2.11    --  107.75 -94.00-180.00  142
 18  \w     35.00  79.00   0.50    2.11    --  107.75 -61.00-120.00   88
 19  \w     35.00  79.00   0.50    2.11    --  107.75 -61.00-180.00   88
 20  \w     35.00  79.00   0.50    2.11    --  107.75 -61.00 -60.00   88
 21  \w     35.00 106.00   0.50    2.11    --  107.75 -94.00   0.00  142
 22  \w     45.00  70.00   0.50    2.11    --  107.75 -61.00  90.00   50
 23  \w     35.00  79.00   0.50    2.11    --  107.75 -61.00  30.00   88
 24  \w     35.00  79.00   0.50    2.11    --  107.75 -61.00 120.00   88
 25  \w     35.00 106.00   0.50    2.11    --  107.75 -94.00 150.00  142
 26  \w     34.00  96.00   0.50    0.53    --   47.95-125.00  30.00  124
 27  \w    -23.00  62.00   0.50    0.53    --   47.95 -53.00-131.00  170
 28  \w    -16.00  28.00   0.50    0.53    --  -47.95  19.00-180.00   88
 29  \w    -43.00 -14.00   0.50    2.11    --  -86.25  45.00-180.00   58
 30  \w   -119.00 -34.00   0.50    0.53    --  -47.95 -53.00-131.00  170
 31  \w   -159.00 -72.00   0.50    2.11    --  -86.25 -53.00-131.00  174
;
_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      0.0472783000
_diffrn_orient_matrix_UB_12      -0.0363661000
_diffrn_orient_matrix_UB_13      -0.0490069000
_diffrn_orient_matrix_UB_21      -0.1318784000
_diffrn_orient_matrix_UB_22      0.0605131000
_diffrn_orient_matrix_UB_23      -0.0280800000
_diffrn_orient_matrix_UB_31      0.1157655000
_diffrn_orient_matrix_UB_32      0.0837387000
_diffrn_orient_matrix_UB_33      -0.0009728000
_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  0.0576
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            41395
_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         77.441
_diffrn_reflns_theta_min         3.240
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.529
_exptl_crystal_description       plate
_exptl_crystal_F_000             1550
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.038
_refine_diff_density_max         1.196
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         6877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0672
_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^)+(0.0919P)^2^+8.4219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1818
_refine_ls_wR_factor_ref         0.1892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5878
_reflns_number_total             6877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02124a2.cif
_cod_data_source_block           a7-dimerno2_yellow
_cod_depositor_comments
'Adding full bibliography for 7060727--7060731.cif.'
_cod_original_cell_volume        3279.36(10)
_cod_original_formula_sum        'C24.75 H23.50 Cl1.50 N2 O4 S9'
_cod_database_code               7060730
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.775
_shelx_estimated_absorpt_t_min   0.288
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(S5A)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(S5)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
 Sof(Cl3S)=Sof(H1SC)=Sof(H1SD)=0.75*(1-FVAR(3))
 Sof(Cl2S)=Sof(H1SA)=Sof(H1SB)=0.75*FVAR(3)
 Fixed Sof: Cl1S(0.75) C1S(0.75)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C1S(H1SC,H1SD), C1S(H1SA,H1SB)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              93145
_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 1.540
_oxdiff_exptl_absorpt_empirical_full_min 0.724