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_7246214
_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_formula_moiety         '2(C32 H28 N2 Si2), C6 F2 N2, 0.75[CH2Cl2]'
_chemical_formula_sum            'C70 H56 F2 N6 Si4'
_chemical_formula_weight         1131.56
_chemical_name_systematic        'PAA F4TCNQ'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-02
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-11-17 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.364(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.921(4)
_cell_length_b                   19.255(2)
_cell_length_c                   25.544(3)
_cell_measurement_reflns_used    28086
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.58
_cell_measurement_theta_min      2.84
_cell_volume                     12981(3)
_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
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.86, Darmstadt 2018
;
_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 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
 776 frames, detector distance = 41 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'X-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            45229
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.644
_diffrn_reflns_theta_max         67.644
_diffrn_reflns_theta_min         3.349
_diffrn_source                   'GeniX 3D Cu Microfocus Source'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.248
_exptl_absorpt_correction_T_max  0.9264
_exptl_absorpt_correction_T_min  0.2417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4736
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     751
_refine_ls_number_reflns         11390
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1707
_refine_ls_R_factor_gt           0.0835
_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^)+(0.0578P)^2^+113.9006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1720
_refine_ls_wR_factor_ref         0.2267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5898
_reflns_number_total             11390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra07322f2.cif
_cod_data_source_block           kt9
_cod_original_cell_volume        12982(3)
_cod_database_code               7246214
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.885
_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. Rigid body (RIGU) restrains
 C1, Si1, C3, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C34, Si4, C33, C35
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 C32(H32), C7(H7), C60(H60), C39(H39), C57(H57), C64(H64), C40(H40), C62(H62),
 C55(H55), C23(H23), C8(H8), C59(H59), C56(H56), C25(H25), C28(H28), C24(H24),
 C63(H63), C31(H31), C27(H27), C30(H30)
3.b Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C46(H46A,H46B,
 H46C), C16(H16A,H16B,H16C), C34(H34A,H34B,H34C), C15(H15A,H15B,H15C), C47(H47A,
 H47B,H47C), C3(H3A,H3B,H3C), C2(H2A,H2B,H2C), C14(H14A,H14B,H14C), C1(H1A,H1B,
 H1C)
;
_smtbx_masks_void_probe_radius   1.15
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              97080
_shelx_fab_checksum              24531
_olex2_submission_special_instructions 'No special instructions were received'