#------------------------------------------------------------------------------
#$Date: 2023-01-31 04:45:18 +0200 (Tue, 31 Jan 2023) $
#$Revision: 280688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/62/7246215.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246215
loop_
_publ_author_name
'Das, Rajorshi'
'Linseis, Michael'
'Schupp, Stefan M.'
'Gogesch, Franciska S.'
'Schmidt-Mende, Lukas'
'Winter, Rainer F.'
_publ_section_title
;
 Organic binary charge-transfer compounds of
 2,2′ : 6′,2′′ : 6′′,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, ω 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/[σ²(Fo²)+(0.0599P)²+0.2176P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.73536(9) 0.82867(9) 0.17606(9) 0.02296(19) Uani 1 1 d . . . . .
F1 F 0.40724(9) 0.73329(9) 0.04364(9) 0.02281(19) Uani 1 1 d . . . . .
O4 O 0.82191(11) 0.59338(12) 0.13523(11) 0.0226(2) Uani 1 1 d . . . . .
O1 O 0.83782(11) 0.58856(11) 0.46479(11) 0.0217(2) Uani 1 1 d . . . . .
O3 O 0.43118(11) 0.75103(11) 0.35831(10) 0.0215(2) Uani 1 1 d . . . . .
O2 O 0.26620(11) 0.17409(11) 0.12548(11) 0.0214(2) Uani 1 1 d . . . . .
N1 N 0.52096(13) 0.50717(13) 0.29436(12) 0.0183(2) Uani 1 1 d . . . . .
C19 C 0.67607(16) 0.55105(15) 0.07304(14) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.34934(16) 0.46255(16) 0.24598(14) 0.0186(3) Uani 1 1 d . . . . .
C21 C 0.45656(16) 0.62293(15) 0.02483(14) 0.0186(3) Uani 1 1 d . . . . .
C18 C 0.79085(16) 0.70752(16) 0.49121(14) 0.0195(3) Uani 1 1 d . . . . .
C6 C 0.42657(16) 0.21791(16) 0.20615(14) 0.0197(3) Uani 1 1 d . . . . .
C20 C 0.61771(16) 0.66956(15) 0.08942(14) 0.0188(3) Uani 1 1 d . . . . .
C8 C 0.22362(16) 0.29688(16) 0.16078(14) 0.0196(3) Uani 1 1 d . . . . .
C13 C 0.63333(16) 0.66808(15) 0.40990(14) 0.0186(3) Uani 1 1 d . . . . .
C12 C 0.30575(16) 0.58495(16) 0.27727(14) 0.0194(3) Uani 1 1 d . . . . .
C14 C 0.58921(16) 0.78942(16) 0.43886(14) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.55215(16) 0.38274(16) 0.29355(14) 0.0188(3) Uani 1 1 d . . . . .
C11 C 0.13820(17) 0.54295(17) 0.22267(15) 0.0226(3) Uani 1 1 d . . . . .
H11 H 0.108615 0.624174 0.243123 0.027 Uiso 1 1 calc R U . . .
C9 C 0.05475(16) 0.25213(17) 0.10562(15) 0.0229(3) Uani 1 1 d . . . . .
H9 H -0.029971 0.141449 0.049262 0.027 Uiso 1 1 calc R U . . .
C3 C 0.74649(17) 0.30220(17) 0.36538(15) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.852428 0.329613 0.419858 0.027 Uiso 1 1 calc R U . . .
C2 C 0.71075(16) 0.42455(16) 0.37481(14) 0.0193(3) Uani 1 1 d . . . . .
C5 C 0.46007(17) 0.09420(17) 0.19361(15) 0.0228(3) Uani 1 1 d . . . . .
H5 H 0.376716 -0.016253 0.133291 0.027 Uiso 1 1 calc R U . . .
C10 C 0.01423(16) 0.37632(17) 0.13624(15) 0.0237(3) Uani 1 1 d . . . . .
H10 H -0.098611 0.347244 0.097971 0.028 Uiso 1 1 calc R U . . .
C4 C 0.62132(17) 0.13772(17) 0.27307(16) 0.0246(3) Uani 1 1 d . . . . .
H4 H 0.645560 0.055100 0.264128 0.030 Uiso 1 1 calc R U . . .
C15 C 0.70324(17) 0.95112(16) 0.54415(15) 0.0221(3) Uani 1 1 d . . . . .
H15 H 0.674950 1.032860 0.561781 0.027 Uiso 1 1 calc R U . . .
C16 C 0.86193(17) 0.98917(16) 0.62354(15) 0.0232(3) Uani 1 1 d . . . . .
H16 H 0.939980 1.097675 0.694545 0.028 Uiso 1 1 calc R U . . .
C17 C 0.90563(16) 0.86795(17) 0.59853(15) 0.0223(3) Uani 1 1 d . . . . .
H17 H 1.010986 0.894713 0.653488 0.027 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 2 -3 0.0610
-6 -2 3 0.0360
1 -5 -3 0.1080
5 -2 -4 0.1270
2 -5 3 0.1000
-1 3 2 0.1050
-3 8 -5 0.0800
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C2 117.35(10) . . ?
C12 O3 C14 117.33(10) . . ?
C8 O2 C6 117.40(10) . . ?
C7 N1 C13 117.00(10) . . ?
C7 N1 C1 116.86(10) . . ?
C13 N1 C1 116.57(10) . . ?
O4 C19 C21 122.81(12) . 2_665 ?
O4 C19 C20 122.86(12) . . ?
C21 C19 C20 114.33(11) 2_665 . ?
C8 C7 N1 120.01(11) . . ?
C8 C7 C12 120.14(11) . . ?
C12 C7 N1 119.77(11) . . ?
F1 C21 C19 115.84(11) . 2_665 ?
F1 C21 C20 121.38(11) . . ?
C20 C21 C19 122.76(11) . 2_665 ?
O1 C18 C13 121.19(11) . . ?
C17 C18 O1 118.67(11) . . ?
C17 C18 C13 120.13(12) . . ?
C1 C6 O2 120.73(11) . . ?
C5 C6 O2 118.63(11) . . ?
C5 C6 C1 120.60(12) . . ?
F2 C20 C19 115.92(11) . . ?
F2 C20 C21 121.19(11) . . ?
C21 C20 C19 122.88(11) . . ?
O2 C8 C7 120.69(11) . . ?
C9 C8 O2 118.91(11) . . ?
C9 C8 C7 120.37(12) . . ?
C18 C13 N1 120.16(11) . . ?
C18 C13 C14 120.05(12) . . ?
C14 C13 N1 119.74(11) . . ?
O3 C12 C7 120.63(11) . . ?
C11 C12 O3 118.92(11) . . ?
C11 C12 C7 120.39(12) . . ?
C13 C14 O3 120.51(11) . . ?
C15 C14 O3 118.76(11) . . ?
C15 C14 C13 120.69(12) . . ?
C6 C1 N1 119.75(11) . . ?
C6 C1 C2 120.08(12) . . ?
C2 C1 N1 120.10(11) . . ?
C12 C11 H11 120.7 . . ?
C12 C11 C10 118.65(12) . . ?
C10 C11 H11 120.7 . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.63(12) . . ?
C10 C9 H9 120.7 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.89(12) . . ?
C4 C3 H3 120.6 . . ?
C1 C2 O1 121.24(11) . . ?
C3 C2 O1 118.50(11) . . ?
C3 C2 C1 120.25(12) . . ?
C6 C5 H5 120.6 . . ?
C6 C5 C4 118.79(12) . . ?
C4 C5 H5 120.6 . . ?
C11 C10 H10 119.1 . . ?
C9 C10 C11 121.80(12) . . ?
C9 C10 H10 119.1 . . ?
C3 C4 C5 121.31(12) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.53(12) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.30(12) . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 119.26(12) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C20 1.3345(14) . ?
F1 C21 1.3326(14) . ?
O4 C19 1.2191(15) . ?
O1 C18 1.3887(15) . ?
O1 C2 1.3888(15) . ?
O3 C12 1.3892(15) . ?
O3 C14 1.3941(15) . ?
O2 C6 1.3921(15) . ?
O2 C8 1.3892(15) . ?
N1 C7 1.3961(16) . ?
N1 C13 1.4050(16) . ?
N1 C1 1.4062(16) . ?
C19 C21 1.4718(18) 2_665 ?
C19 C20 1.4724(17) . ?
C7 C8 1.3903(18) . ?
C7 C12 1.3948(17) . ?
C21 C20 1.3358(18) . ?
C18 C13 1.3892(17) . ?
C18 C17 1.3804(19) . ?
C6 C1 1.3872(18) . ?
C6 C5 1.3785(18) . ?
C8 C9 1.3837(17) . ?
C13 C14 1.3905(17) . ?
C12 C11 1.3803(18) . ?
C14 C15 1.3809(18) . ?
C1 C2 1.3883(17) . ?
C11 H11 0.9300 . ?
C11 C10 1.3940(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3935(18) . ?
C3 H3 0.9300 . ?
C3 C2 1.3855(18) . ?
C3 C4 1.3907(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.3954(18) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.3961(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.3913(18) . ?
C17 H17 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C21 C20 F2 0.4(2) . . . . ?
F1 C21 C20 C19 179.03(11) . . . . ?
O4 C19 C20 F2 0.74(19) . . . . ?
O4 C19 C20 C21 -177.98(12) . . . . ?
O1 C18 C13 N1 -2.64(18) . . . . ?
O1 C18 C13 C14 179.81(11) . . . . ?
O1 C18 C17 C16 178.42(12) . . . . ?
O3 C12 C11 C10 177.39(12) . . . . ?
O3 C14 C15 C16 -179.43(11) . . . . ?
O2 C6 C1 N1 -3.59(18) . . . . ?
O2 C6 C1 C2 179.21(11) . . . . ?
O2 C6 C5 C4 179.33(12) . . . . ?
O2 C8 C9 C10 -177.35(12) . . . . ?
N1 C7 C8 O2 1.34(18) . . . . ?
N1 C7 C8 C9 -176.50(12) . . . . ?
N1 C7 C12 O3 -1.06(18) . . . . ?
N1 C7 C12 C11 176.18(12) . . . . ?
N1 C13 C14 O3 2.70(18) . . . . ?
N1 C13 C14 C15 -175.05(12) . . . . ?
N1 C1 C2 O1 3.72(18) . . . . ?
N1 C1 C2 C3 -175.10(12) . . . . ?
C19 C21 C20 F2 179.13(11) 2_665 . . . ?
C19 C21 C20 C19 -2.2(2) 2_665 . . . ?
C7 N1 C13 C18 162.42(11) . . . . ?
C7 N1 C13 C14 -20.03(17) . . . . ?
C7 N1 C1 C6 19.81(17) . . . . ?
C7 N1 C1 C2 -162.99(11) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C7 C12 C11 C10 0.1(2) . . . . ?
C21 C19 C20 F2 -179.24(10) 2_665 . . . ?
C21 C19 C20 C21 2.0(2) 2_665 . . . ?
C18 O1 C2 C1 11.07(17) . . . . ?
C18 O1 C2 C3 -170.09(11) . . . . ?
C18 C13 C14 O3 -179.75(11) . . . . ?
C18 C13 C14 C15 2.50(19) . . . . ?
C6 O2 C8 C7 15.08(17) . . . . ?
C6 O2 C8 C9 -167.04(11) . . . . ?
C6 C1 C2 O1 -179.09(11) . . . . ?
C6 C1 C2 C3 2.08(19) . . . . ?
C6 C5 C4 C3 0.9(2) . . . . ?
C8 O2 C6 C1 -13.92(17) . . . . ?
C8 O2 C6 C5 168.17(11) . . . . ?
C8 C7 C12 O3 -177.97(11) . . . . ?
C8 C7 C12 C11 -0.7(2) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C13 N1 C7 C8 -163.87(11) . . . . ?
C13 N1 C7 C12 19.21(17) . . . . ?
C13 N1 C1 C6 165.13(11) . . . . ?
C13 N1 C1 C2 -17.67(17) . . . . ?
C13 C18 C17 C16 -0.29(19) . . . . ?
C13 C14 C15 C16 -1.64(19) . . . . ?
C12 O3 C14 C13 15.54(17) . . . . ?
C12 O3 C14 C15 -166.66(11) . . . . ?
C12 C7 C8 O2 178.25(11) . . . . ?
C12 C7 C8 C9 0.41(19) . . . . ?
C12 C11 C10 C9 0.9(2) . . . . ?
C14 O3 C12 C7 -16.40(17) . . . . ?
C14 O3 C12 C11 166.32(12) . . . . ?
C14 C15 C16 C17 -0.18(19) . . . . ?
C1 N1 C7 C8 -18.70(17) . . . . ?
C1 N1 C7 C12 164.38(11) . . . . ?
C1 N1 C13 C18 17.14(17) . . . . ?
C1 N1 C13 C14 -165.31(11) . . . . ?
C1 C6 C5 C4 1.4(2) . . . . ?
C2 O1 C18 C13 -11.61(17) . . . . ?
C2 O1 C18 C17 169.69(11) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C5 C6 C1 N1 174.28(12) . . . . ?
C5 C6 C1 C2 -2.92(19) . . . . ?
C4 C3 C2 O1 -178.65(12) . . . . ?
C4 C3 C2 C1 0.21(19) . . . . ?
C15 C16 C17 C18 1.1(2) . . . . ?
C17 C18 C13 N1 176.03(12) . . . . ?
C17 C18 C13 C14 -1.51(19) . . . . ?
