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#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/65/4516523.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_4516523
loop_
_publ_author_name
'Kataeva, Olga'
'Khrizanforov, Mikhail'
'Budnikova, Yulia'
'Islamov, Daut'
'Burganov, Timur'
'Vandyukov, Alexander'
'Lyssenko, Konstantin'
'Mahns, Benjamin'
'Nohr, Markus'
'Hampel, Silke'
'Knupfer, Martin'
_publ_section_title
;
 Crystal Growth, Dynamic and Charge Transfer Properties of New Coronene
 Charge Transfer Complexes
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              331
_journal_paper_doi               10.1021/acs.cgd.5b01301
_journal_volume                  16
_journal_year                    2015
_chemical_formula_moiety         'C24 H12, C12 F4 N4, C2 H3 N'
_chemical_formula_sum            'C38 H15 F4 N5'
_chemical_formula_weight         617.55
_chemical_name_common            'Coronene F4TCNQ acetonitrile'
_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'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.494(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6173(6)
_cell_length_b                   6.9678(2)
_cell_length_c                   18.3594(5)
_cell_measurement_reflns_used    2780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.44
_cell_measurement_theta_min      4.98
_cell_volume                     2677.37(13)
_computing_cell_refinement       'APEX2  v2, 1-4  (Bruker AXS, 2005-2007)'
_computing_data_collection       'APEX2  v2, 1-4  (Bruker AXS, 2005-2007)'
_computing_data_reduction        'SAINT NT v6.0 (Bruker AXS, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18373
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.479
_diffrn_reflns_theta_max         66.479
_diffrn_reflns_theta_min         4.225
_diffrn_source                   'microfocus tube'
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  0.9715
_exptl_absorpt_correction_T_min  0.7596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       needle
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0341
_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)+(0.1000P)²+0.2287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1964
_reflns_number_total             2352
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b01301_si_009.cif
_cod_data_source_block           mar136-100k
_cod_original_cell_volume        2677.38(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4516523
_shelx_shelxl_version_number     2014/7
_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_min   0.760
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C1 C 0.18307(7) 0.3506(2) 0.66515(8) 0.0229(3) Uani 1 1 d . . . . .
H1 H 0.1801 0.3895 0.7138 0.028 Uiso 1 1 calc R U . . .
C2 C 0.12980(7) 0.2827(2) 0.61483(9) 0.0230(3) Uani 1 1 d . . . . .
H2 H 0.0906 0.2745 0.6292 0.028 Uiso 1 1 calc R U . . .
C3 C 0.07758(7) 0.1536(2) 0.48731(9) 0.0220(3) Uani 1 1 d . . . . .
H3 H 0.0380 0.1439 0.5007 0.026 Uiso 1 1 calc R U . . .
C4 C 0.08075(7) 0.0994(2) 0.41668(8) 0.0216(3) Uani 1 1 d . . . . .
H4 H 0.0434 0.0536 0.3819 0.026 Uiso 1 1 calc R U . . .
C5 C 0.14417(7) 0.0553(2) 0.32181(8) 0.0229(3) Uani 1 1 d . . . . .
H5 H 0.1074 0.0096 0.2861 0.027 Uiso 1 1 calc R U . . .
C6 C 0.20091(7) 0.0667(2) 0.30242(8) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.2030 0.0277 0.2535 0.028 Uiso 1 1 calc R U . . .
C7 C 0.13209(7) 0.2240(2) 0.54120(8) 0.0201(3) Uani 1 1 d . . . . .
C8 C 0.13918(7) 0.1110(2) 0.39475(8) 0.0202(3) Uani 1 1 d . . . . .
C9 C 0.25719(7) 0.1358(2) 0.35381(8) 0.0206(3) Uani 1 1 d . . . . .
C10 C 0.19083(7) 0.2368(2) 0.52053(8) 0.0186(3) Uani 1 1 d . . . . .
C11 C 0.19431(7) 0.1803(2) 0.44716(8) 0.0188(3) Uani 1 1 d . . . . .
C12 C 0.25346(7) 0.1929(2) 0.42643(8) 0.0188(3) Uani 1 1 d . . . . .
C13 C 0.20124(7) 0.6781(2) 0.44265(8) 0.0181(3) Uani 1 1 d . . . . .
F13 F 0.15484(4) 0.60930(13) 0.38667(4) 0.0213(2) Uani 1 1 d . . . . .
C14 C 0.18611(7) 0.7294(2) 0.51216(8) 0.0180(3) Uani 1 1 d . . . . .
C15 C 0.23971(7) 0.8026(2) 0.56849(8) 0.0181(3) Uani 1 1 d . . . . .
F15 F 0.23042(4) 0.85433(13) 0.63499(4) 0.0214(2) Uani 1 1 d . . . . .
C16 C 0.12565(7) 0.7115(2) 0.52337(8) 0.0189(3) Uani 1 1 d . . . . .
C17 C 0.07211(7) 0.6374(2) 0.46770(8) 0.0207(3) Uani 1 1 d . . . . .
N17 N 0.02667(6) 0.5794(2) 0.42702(7) 0.0249(3) Uani 1 1 d . . . . .
C18 C 0.10824(6) 0.7692(2) 0.59062(8) 0.0201(3) Uani 1 1 d . . . . .
N18 N 0.08933(6) 0.8160(2) 0.64111(7) 0.0264(3) Uani 1 1 d . . . . .
C19 C 0.49117(18) -0.0674(4) 0.2459(3) 0.0308(4) Uani 0.5 1 d . . P A -1
H19A H 0.5200 -0.1238 0.2182 0.046 Uiso 0.5 1 calc R U P A -1
H19B H 0.4468 -0.0971 0.2199 0.046 Uiso 0.5 1 calc R U P A -1
H19C H 0.5008 -0.1207 0.2969 0.046 Uiso 0.5 1 calc R U P A -1
C20 C 0.5000 0.1416(4) 0.2500 0.0308(4) Uani 1 2 d S T P . .
N20 N 0.5036(3) 0.3060(4) 0.2435(3) 0.0308(4) Uani 0.5 1 d . . P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 C1 C9 121.35(14) . 7_556
C2 C1 H1 119.3 . .
C9 C1 H1 119.3 7_556 .
C1 C2 C7 121.11(14) . .
C1 C2 H2 119.4 . .
C7 C2 H2 119.4 . .
C4 C3 C7 121.66(13) . .
C4 C3 H3 119.2 . .
C7 C3 H3 119.2 . .
C3 C4 C8 120.77(13) . .
C3 C4 H4 119.6 . .
C8 C4 H4 119.6 . .
C6 C5 C8 120.99(13) . .
C6 C5 H5 119.5 . .
C8 C5 H5 119.5 . .
C5 C6 C9 121.50(14) . .
C5 C6 H6 119.3 . .
C9 C6 H6 119.3 . .
C10 C7 C3 118.51(13) . .
C10 C7 C2 118.85(13) . .
C3 C7 C2 122.63(13) . .
C11 C8 C4 118.91(14) . .
C11 C8 C5 118.88(13) . .
C4 C8 C5 122.21(13) . .
C12 C9 C1 118.80(13) . 7_556
C12 C9 C6 118.65(13) . .
C1 C9 C6 122.55(14) 7_556 .
C7 C10 C11 119.97(13) . .
C7 C10 C12 119.80(14) . 7_556
C11 C10 C12 120.23(13) . 7_556
C8 C11 C10 120.17(13) . .
C8 C11 C12 119.89(14) . .
C10 C11 C12 119.94(13) . .
C9 C12 C11 120.09(13) . .
C9 C12 C10 120.08(13) . 7_556
C11 C12 C10 119.83(14) . 7_556
F13 C13 C15 118.50(13) . 7_566
F13 C13 C14 118.61(12) . .
C15 C13 C14 122.89(13) 7_566 .
C16 C14 C15 123.20(13) . .
C16 C14 C13 122.96(13) . .
C15 C14 C13 113.85(13) . .
F15 C15 C13 118.43(12) . 7_566
F15 C15 C14 118.31(12) . .
C13 C15 C14 123.26(13) 7_566 .
C14 C16 C17 123.51(13) . .
C14 C16 C18 124.43(13) . .
C17 C16 C18 112.03(12) . .
N17 C17 C16 174.94(15) . .
N18 C18 C16 174.52(15) . .
C20 C19 H19A 109.5 . .
C20 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C20 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
N20 C20 C19 171.3(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.368(2) .
C1 C9 1.422(2) 7_556
C1 H1 0.9500 .
C2 C7 1.425(2) .
C2 H2 0.9500 .
C3 C4 1.369(2) .
C3 C7 1.423(2) .
C3 H3 0.9500 .
C4 C8 1.421(2) .
C4 H4 0.9500 .
C5 C6 1.362(2) .
C5 C8 1.424(2) .
C5 H5 0.9500 .
C6 C9 1.424(2) .
C6 H6 0.9500 .
C7 C10 1.416(2) .
C8 C11 1.416(2) .
C9 C12 1.413(2) .
C9 C1 1.422(2) 7_556
C10 C11 1.423(2) .
C10 C12 1.432(2) 7_556
C11 C12 1.425(2) .
C12 C10 1.432(2) 7_556
C13 F13 1.3326(16) .
C13 C15 1.349(2) 7_566
C13 C14 1.440(2) .
C14 C16 1.379(2) .
C14 C15 1.439(2) .
C15 F15 1.3355(16) .
C15 C13 1.349(2) 7_566
C16 C17 1.435(2) .
C16 C18 1.435(2) .
C17 N17 1.149(2) .
C18 N18 1.150(2) .
C19 C20 1.468(4) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 N20 1.156(4) .
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_4
C9 C1 C2 C7 -0.4(2) 7_556 .
C7 C3 C4 C8 0.3(2) . .
C8 C5 C6 C9 -0.5(2) . .
C4 C3 C7 C10 -0.3(2) . .
C4 C3 C7 C2 179.48(14) . .
C1 C2 C7 C10 0.1(2) . .
C1 C2 C7 C3 -179.69(14) . .
C3 C4 C8 C11 -0.2(2) . .
C3 C4 C8 C5 179.83(14) . .
C6 C5 C8 C11 0.5(2) . .
C6 C5 C8 C4 -179.57(14) . .
C5 C6 C9 C12 0.1(2) . .
C5 C6 C9 C1 -179.85(14) . 7_556
C3 C7 C10 C11 0.1(2) . .
C2 C7 C10 C11 -179.61(13) . .
C3 C7 C10 C12 -179.96(13) . 7_556
C2 C7 C10 C12 0.3(2) . 7_556
C4 C8 C11 C10 0.1(2) . .
C5 C8 C11 C10 -179.95(13) . .
C4 C8 C11 C12 179.94(13) . .
C5 C8 C11 C12 -0.1(2) . .
C7 C10 C11 C8 -0.1(2) . .
C12 C10 C11 C8 -179.97(13) 7_556 .
C7 C10 C11 C12 -179.91(13) . .
C12 C10 C11 C12 0.2(2) 7_556 .
C1 C9 C12 C11 -179.78(13) 7_556 .
C6 C9 C12 C11 0.2(2) . .
C1 C9 C12 C10 0.0(2) 7_556 7_556
C6 C9 C12 C10 -179.97(13) . 7_556
C8 C11 C12 C9 -0.2(2) . .
C10 C11 C12 C9 179.59(13) . .
C8 C11 C12 C10 179.97(13) . 7_556
C10 C11 C12 C10 -0.2(2) . 7_556
F13 C13 C14 C16 -0.3(2) . .
C15 C13 C14 C16 179.34(13) 7_566 .
F13 C13 C14 C15 -179.79(12) . .
C15 C13 C14 C15 -0.2(2) 7_566 .
C16 C14 C15 F15 0.5(2) . .
C13 C14 C15 F15 179.96(12) . .
C16 C14 C15 C13 -179.34(13) . 7_566
C13 C14 C15 C13 0.2(2) . 7_566
C15 C14 C16 C17 -179.54(13) . .
C13 C14 C16 C17 1.0(2) . .
C15 C14 C16 C18 2.4(2) . .
C13 C14 C16 C18 -177.08(14) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346173
