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_7242689
_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         'C9 H8 S'
_chemical_formula_sum            'C9 H8 S'
_chemical_formula_weight         148.21
_chemical_name_systematic        tetramethyldithiopyrene
_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             2020-07-31
_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                105.537(3)
_cell_angle_beta                 90.439(3)
_cell_angle_gamma                96.653(3)
_cell_formula_units_Z            2
_cell_length_a                   3.9618(4)
_cell_length_b                   9.2110(8)
_cell_length_c                   9.8478(8)
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.889
_cell_measurement_theta_min      2.697
_cell_volume                     343.62(5)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.999
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14877
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.724
_diffrn_reflns_theta_min         2.148
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1253 before and 0.0927 after correction. The Ratio of minimum to maximum transmission is 0.9045. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.183
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0408P)^2^+0.1158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2392
_reflns_number_total             2736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra00587a2.cif
_cod_data_source_block           mo_d8v4529_0m_a
_cod_database_code               7242689
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.856
_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:
 C1(H1), C4(H4)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_olex2_exptl_crystal_mounting_method 'silicone grease on kapton loop'
_olex2_submission_special_instructions 'No special instructions were received'