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_7060728
_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         'C26 H26 O2 S8'
_chemical_formula_sum            'C26 H26 O2 S8'
_chemical_formula_weight         626.95
_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             2020-03-13
_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                98.3050(10)
_cell_angle_beta                 93.3530(10)
_cell_angle_gamma                94.9550(10)
_cell_formula_units_Z            4
_cell_length_a                   10.11380(10)
_cell_length_b                   13.0705(2)
_cell_length_c                   21.6545(2)
_cell_measurement_reflns_used    23110
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2050
_cell_measurement_theta_min      3.4190
_cell_volume                     2814.64(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.985
_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     31.00 120.00   0.50    2.17    --   47.70  61.00   8.00  178
  2  \w     91.00 178.00   0.50    8.67    --  107.75  61.00   8.00  174
  3  \w     95.00 178.00   0.50    8.67    --  107.75  45.00 -30.00  166
  4  \w     95.00 178.00   0.50    8.67    --  107.75  30.00  60.00  166
  5  \w     95.00 178.00   0.50    8.67    --  107.75  45.00   0.00  166
  6  \w     95.00 178.00   0.50    8.67    --  107.75  45.00-150.00  166
  7  \w     94.00 178.00   0.50    8.67    --  107.75  15.00 -60.00  168
  8  \w     95.00 178.00   0.50    8.67    --  107.75  45.00  90.00  166
  9  \w     95.00 178.00   0.50    8.67    --  107.75 125.00 120.00  166
 10  \w     85.00 178.00   0.50    8.67    --  107.75  77.00 -60.00  186
 11  \w     94.00 178.00   0.50    8.67    --  107.75  15.00-120.00  168
 12  \w     35.00  79.00   0.50    8.67    --  107.75 -61.00-130.00   88
 13  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00 -60.00  142
 14  \w     38.00  72.00   0.50    8.67    --  107.75 -61.00  30.00   68
 15  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00 -30.00  142
 16  \w     34.00  95.00   0.50    2.17    --   47.70-125.00  90.00  122
 17  \w     35.00 106.00   0.50    8.67    --  107.75-100.00  95.83  142
 18  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00 120.00  142
 19  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00 150.00  142
 20  \w     35.00 131.00   0.50    8.67    --  107.75 -77.00  30.00  192
 21  \w     94.00 178.00   0.50    8.67    --  107.75  15.00 150.00  168
 22  \w     35.00 107.00   0.50    8.67    --  107.75-107.00   3.46  144
 23  \w     35.00  79.00   0.50    8.67    --  107.75 -61.00  90.00   88
 24  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00  30.00  142
 25  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00 -90.00  142
 26  \w     35.00 112.00   0.50    8.67    --  107.75-125.00-180.00  154
 27  \w     35.00  79.00   0.50    8.67    --  107.75 -61.00-180.00   88
 28  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00-120.00  142
 29  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00   0.00  142
 30  \w     35.00 112.00   0.50    8.67    --  107.75-125.00 -30.00  154
 31  \w     35.00 107.00   0.50    8.67    --  107.75-105.00-173.92  144
 32  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00-150.00  142
 33  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00-180.00  142
 34  \w     35.00 112.00   0.50    8.67    --  107.75-125.00 -60.00  154
 35  \w     35.00 106.00   0.50    8.67    --  107.75 -94.00  60.00  142
 36  \w     35.00 108.00   0.50    8.67    --  107.75-110.00-112.65  146
 37  \w     35.00 112.00   0.50    8.67    --  107.75-125.00-120.00  154
 38  \w    -27.00  30.00   0.50    2.17    --   47.70 -19.00 -90.00  114
 39  \w    -24.00  64.00   0.50    2.17    --   47.70 -61.00-130.00  176
 40  \w    -16.00  28.00   0.50    2.17    --  -47.70  19.00 -60.00   88
 41  \w    -43.00 -14.00   0.50    8.67    --  -86.25  45.00-150.00   58
 42  \w    -65.00 -13.00   0.50    8.67    --  -86.25  61.00-180.00  104
 43  \w    -64.00  25.00   0.50    2.17    --  -47.70  61.00   8.00  178
 44  \w    -16.00  28.00   0.50    2.17    --  -47.70  19.00 120.00   88
 45  \w    -43.00 -14.00   0.50    8.67    --  -86.25  45.00 120.00   58
 46  \w    -65.00 -13.00   0.50    8.67    --  -86.25  61.00   8.00  104
 47  \w   -119.00 -31.00   0.50    2.17    --  -47.70 -61.00-130.00  176
 48  \w   -119.00 -73.00   0.50    2.17    --  -47.70-125.00  60.00   92
 49  \w   -119.00 -73.00   0.50    2.17    --  -47.70-125.00 -30.00   92
 50  \w   -159.00 -70.00   0.50    8.67    --  -86.25 -61.00-130.00  178
;
_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      -0.0445788000
_diffrn_orient_matrix_UB_12      -0.1009605000
_diffrn_orient_matrix_UB_13      0.0251053000
_diffrn_orient_matrix_UB_21      -0.1255904000
_diffrn_orient_matrix_UB_22      -0.0157506000
_diffrn_orient_matrix_UB_23      -0.0454203000
_diffrn_orient_matrix_UB_31      0.0757522000
_diffrn_orient_matrix_UB_32      -0.0622824000
_diffrn_orient_matrix_UB_33      -0.0500278000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22234
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.658
_diffrn_reflns_theta_min         2.067
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       plate
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         22234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0651
_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^)+(0.1043P)^2^+6.2614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.1957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18156
_reflns_number_total             22234
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 1.5233\% 
 around [0.64 -0.21 -0.74] (reciprocal) or [0.95 -0.20 -0.24] (direct)
;
_cod_data_source_file            d1nj02124a2.cif
_cod_data_source_block           p-och3_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7060727--7060731.cif.'
_cod_original_cell_volume        2814.63(6)
_cod_database_code               7060728
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C26H26O2S8
_shelx_estimated_absorpt_t_max   0.751
_shelx_estimated_absorpt_t_min   0.539
_diffrn_oxdiff_digest_frames
;
0177539f48f817f3222ac28f72244cd0d90694400a7
;
_diffrn_oxdiff_digest_hkl
;
01ef5dd9a0189fbef3a7680fe68e746057f1bf
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4657(15)
 0.5343(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C21(H21), C22(H22), C24(H24), C25(H25),
 C34(H34), C35(H35), C37(H37), C38(H38), C47(H47), C48(H48), C50(H50), C51(H51)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C),
 C19(H19A,H19B,H19C), C26(H26A,H26B,H26C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C39(H39A,H39B,H39C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C52(H52A,
 H52B,H52C)
;
_shelx_res_checksum              72464
_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 1.582
_oxdiff_exptl_absorpt_empirical_full_min 0.657
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2