Charge transfer in mixed and segregated stacks of tetrathiafulvalene, tetrathianaphthalene and naphthalene diimide: a structural, spectroscopic and computational study
Leong, Chanel F.; Chan, Bun; Liu, Tianfu; Moore, Harrison S.; Hod, Idan; Solomon, Marcello B.; Usov, Pavel M.; Hupp, Joseph T.; Farha, Omar; D’Alessandro, Deanna M.; New Journal of Chemistry 46 (2022) 10026–10036; doi:10.1039/D2NJ00643J

data_7061489
_publ_section_title
;
 Charge transfer in mixed and segregated stacks of tetrathiafulvalene,
 tetrathianaphthalene and naphthalene diimide: a structural, spectroscopic
 and computational study
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10026
_journal_page_last               10036
_journal_paper_doi               10.1039/D2NJ00643J
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C24 H12 N4 O4, C6 H4 S4'
_chemical_formula_sum            'C30 H16 N4 O4 S4'
_chemical_formula_weight         624.71
_chemical_name_systematic
'2,7-bis(pyridin-4-yl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone [1,4]dithiino[2,3-b][1,4]dithiine'
_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     direct
_audit_creation_date             2022-03-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-29 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.51
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.044
_cell_length_b                   8.232
_cell_length_c                   11.711
_cell_measurement_reflns_used    9458
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.24
_cell_volume                     1316.447
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      299.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11251
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.261
_diffrn_reflns_theta_min         3.236
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.721
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0384 after correction.
The Ratio of minimum to maximum transmission is 0.7282.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0460P)^2^+0.4216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0823
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2328
_reflns_number_total             2375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj00643j2.cif
_cod_data_source_block           TTN-DPNI
_cod_depositor_comments
'Adding full bibliography for 7061488--7061490.cif.'
_cod_original_cell_volume        1316.4
_cod_database_code               7061489
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.897
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C4(H4), C1(H1), C2(H2), C5(H5), C14(H14), C15(H15)
;
_shelx_res_checksum              41821
_olex2_submission_special_instructions 'No special instructions were received'