Organic binary charge-transfer compounds of 2,2′ : 6′,2′′ : 6′′,6-trioxotriphenylamine and a pyrene-annulated azaacene as donors
Das, Rajorshi; Linseis, Michael; Schupp, Stefan M.; Gogesch, Franciska S.; Schmidt-Mende, Lukas; Winter, Rainer F.; RSC Advances 13 (2023) 3652–3660; doi:10.1039/D2RA07322F

data_7246215
_publ_section_title
;
 Organic binary charge-transfer compounds of
 2,2&#x2032;&#x2009;:&#x2009;6&#x2032;,2&#x2032;&#x2032;&#x2009;:&#x2009;6&#x2032;&#x2032;,6-trioxotriphenylamine
 and a pyrene-annulated azaacene as donors
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              3652
_journal_page_last               3660
_journal_paper_doi               10.1039/D2RA07322F
_journal_volume                  13
_journal_year                    2023
_chemical_compound_source        Dichloromethane
_chemical_formula_moiety         'C3 F2 O, C18 H9 N O3'
_chemical_formula_sum            'C21 H9 F2 N O4'
_chemical_formula_weight         377.29
_chemical_name_systematic        'TOTA F4BQ'
_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             2022-11-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-17 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                112.442(5)
_cell_angle_beta                 94.726(5)
_cell_angle_gamma                115.784(5)
_cell_formula_units_Z            2
_cell_length_a                   9.0452(6)
_cell_length_b                   10.1512(7)
_cell_length_c                   10.1574(7)
_cell_measurement_reflns_used    6284
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.52
_cell_volume                     740.80(11)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
 239 frames, detector distance = 80 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6260
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         2.486
_diffrn_source
'Sealed Mo X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.8496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0599P)^2^+0.2176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2678
_reflns_number_total             3312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra07322f2.cif
_cod_data_source_block           raj255
_cod_original_cell_volume        740.80(10)
_cod_database_code               7246215
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C3(H3), C5(H5), C10(H10), C4(H4), C15(H15), C16(H16),
 C17(H17)
;
_shelx_res_checksum              74221
_olex2_submission_special_instructions 'No special instructions were received'