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_7242688
_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         '0.16(C18 H16 S2), 0.11(F6 P), 0.11(C4 H8 O)'
_chemical_formula_sum            'C3.26 H3.37 F0.63 O0.11 P0.11 S0.32'
_chemical_formula_weight         69.65
_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             2020-07-23
_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                71.857(10)
_cell_angle_beta                 77.095(10)
_cell_angle_gamma                72.995(10)
_cell_formula_units_Z            19
_cell_length_a                   10.825(4)
_cell_length_b                   11.925(4)
_cell_length_c                   12.194(4)
_cell_measurement_reflns_used    6531
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.774
_cell_measurement_theta_min      2.450
_cell_volume                     1415.2(9)
_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)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.642
_diffrn_measured_fraction_theta_max 0.958
_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  0.0837
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.642
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13127
_diffrn_reflns_point_group_measured_fraction_full 0.642
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         21.874
_diffrn_reflns_theta_min         2.369
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1231 before and 0.0884 after correction. The Ratio of minimum to maximum transmission is 0.8249. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             686
_exptl_crystal_preparation       'From THF'
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.131
_refine_diff_density_max         1.030
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.1392
_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^)+(0.1111P)^2^+40.1471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3674
_refine_ls_wR_factor_ref         0.3821
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2480
_reflns_number_total             3278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra00587a2.cif
_cod_data_source_block           d8v4392_0m_a
_cod_original_cell_volume        1415.2(8)
_cod_database_code               7242688
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.944
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C00I, C00K, C00X, C00T, C00L, C00R, C17, C00Q, C00U, C00Z, C00G, C00E, C00D,
 C00M, C00P, C00H, C010, C00J, C00O, C00F, C00W
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C013(H01G,H01H), C014(H01I,H01J), C015(H01K,H01L), C016(H01M,H01N)
3.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00K(H00K), C00M(H00M), C00P(H00P), C00T(H00T)
3.c Idealised Me refined as rotating group:
 C00N(H00H,H00I,H00L), C00S(H00A,H00B,H00C), C00V(H00N,H00O,H00Q), C00Y(H00D,
 H00E,H00F), C011(H01A,H01B,H01C), C012(H01D,H01E,H01F)
;
_olex2_exptl_crystal_mounting_method 'silicone grease on kapton loop'
_olex2_submission_special_instructions 'No special instructions were received'