A new donor for charge-transfer systems: synthesis and properties of 2,4,7,9-tetramethyl-1,6-dithiapyrene (TMDTP) and structure of (TMDTP)3(PF6)2·2THF and TMDTP‒TCNQ
Bendix, Jesper; Bechgaard, Klaus; Christensen, Jørn Bolstad; RSC Advances 11 (2021) 14607–14614; doi:10.1039/D1RA00587A

data_7242690
_publ_section_title
;
 A new donor for charge-transfer systems: synthesis and properties of
 2,4,7,9-tetramethyl-1,6-dithiapyrene (TMDTP) and structure of
 (TMDTP)3(PF6)2&#x00B7;2THF and TMDTP--TCNQ
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              14607
_journal_page_last               14614
_journal_paper_doi               10.1039/D1RA00587A
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         '2(C9 H8 S), C12 H4 N4'
_chemical_formula_sum            'C30 H20 N4 S2'
_chemical_formula_weight         500.62
_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
_audit_creation_date             2020-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-22 deposited with the CCDC.	2021-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                82.379(4)
_cell_angle_beta                 89.939(3)
_cell_angle_gamma                86.046(4)
_cell_formula_units_Z            2
_cell_length_a                   3.7098(3)
_cell_length_b                   17.1976(18)
_cell_length_c                   20.181(2)
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.239
_cell_measurement_theta_min      2.396
_cell_volume                     1273.1(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            69129
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.475
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1000 before and 0.0755 after correction. The Ratio of minimum to maximum transmission is 0.9399. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.078
_refine_diff_density_max         1.337
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0961
_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^)+(0.0724P)^2^+9.1065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2371
_refine_ls_wR_factor_ref         0.2448
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4801
_reflns_number_total             5812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra00587a2.cif
_cod_data_source_block           d8v4373_1_0m_a
_cod_database_code               7242690
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.893
_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:
 C5(H5), C9(H9), C13(H13), C14(H14), C19(H19), C20(H20), C27(H27), C29(H29)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C22(H22A,H22B,H22C), C30(H30A,H30B,H30C)
;
_olex2_exptl_crystal_mounting_method 'silicone grease on kapton loop'
_olex2_submission_special_instructions 'No special instructions were received'