#------------------------------------------------------------------------------
#$Date: 2025-08-22 16:55:42 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301864 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/37/7213761.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_7213761
loop_
_publ_author_name
'Dobrowolski, Michał A.'
'Garbarino, Gaston'
'Mezouar, Mohamed'
'Ciesielski, Arkadiusz'
'Cyrański, Michał K.'
_publ_section_title
;
 Structural diversities of charge transfer organic complexes. Focus on
 benzenoid hydrocarbons and 7,7,8,8-tetracyanoquinodimethane
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              415
_journal_paper_doi               10.1039/c3ce41703d
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H4 N4, 2(C16 H10)'
_chemical_formula_sum            'C44 H24 N4'
_chemical_formula_weight         608.67
_chemical_name_systematic
; 
 Pyrene-7,7,8,8-tetracyanoquinodimethane complex (2:1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.42(5)
_cell_angle_beta                 106.46(3)
_cell_angle_gamma                93.44(4)
_cell_formula_units_Z            1
_cell_length_a                   7.004(2)
_cell_length_b                   10.090(5)
_cell_length_c                   11.783(5)
_cell_measurement_temperature    100(2)
_cell_volume                     752.4(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2214
_diffrn_reflns_av_sigmaI/netI    0.1286
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10917
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0945
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1590P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2292
_refine_ls_wR_factor_ref         0.2737
_reflns_number_gt                1454
_reflns_number_total             2667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41703d.txt
_cod_data_source_block           pyrentq
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7213761
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
C1 C 0.0621(5) 0.6450(4) 0.0309(4) 0.0395(10) Uani 1 1 d
C2 C -0.0274(5) 0.5563(4) -0.0984(4) 0.0386(10) Uani 1 1 d
H2 H -0.053(6) 0.600(4) -0.167(4) 0.042(11) Uiso 1 1 d
C3 C 0.1229(5) 0.7864(4) 0.0573(4) 0.0393(10) Uani 1 1 d
N7 N 0.0658(5) 0.8966(4) -0.1174(4) 0.0491(10) Uani 1 1 d
C5 C 0.0875(5) 0.5839(4) 0.1264(4) 0.0401(10) Uani 1 1 d
H5 H 0.158(6) 0.659(4) 0.217(4) 0.047(11) Uiso 1 1 d
N8 N 0.2987(6) 0.9483(4) 0.2858(4) 0.0571(11) Uani 1 1 d
C4 C 0.0945(6) 0.8486(4) -0.0376(4) 0.0407(10) Uani 1 1 d
C6 C 0.2196(6) 0.8781(4) 0.1843(4) 0.0450(11) Uani 1 1 d
C9 C 0.5109(5) 0.5640(4) 0.9865(4) 0.0376(9) Uani 1 1 d
C10 C 0.4420(5) 0.5624(4) 0.8599(4) 0.0389(10) Uani 1 1 d
C11 C 0.5998(5) 0.6921(4) 1.0858(4) 0.0396(10) Uani 1 1 d
C12 C 0.4650(6) 0.6889(5) 0.8362(4) 0.0439(10) Uani 1 1 d
H12 H 0.404(6) 0.685(4) 0.739(4) 0.040(10) Uiso 1 1 d
C13 C 0.3542(6) 0.4310(4) 0.7624(4) 0.0425(10) Uani 1 1 d
H13 H 0.323(5) 0.435(4) 0.672(4) 0.032(9) Uiso 1 1 d
C14 C 0.6662(6) 0.6896(5) 1.2119(4) 0.0437(10) Uani 1 1 d
H14 H 0.723(7) 0.784(5) 1.279(4) 0.053(12) Uiso 1 1 d
C15 C 0.6206(6) 0.8163(4) 1.0565(4) 0.0456(11) Uani 1 1 d
H15 H 0.685(6) 0.909(4) 1.127(4) 0.041(10) Uiso 1 1 d
C16 C 0.5544(6) 0.8143(5) 0.9347(4) 0.0493(11) Uani 1 1 d
H16 H 0.557(7) 0.908(5) 0.908(4) 0.064(13) Uiso 1 1 d
C17 C 0.0430(6) 0.5690(4) 0.5063(3) 0.0396(10) Uani 1 1 d
C18 C 0.2074(6) 0.5845(4) 0.4605(3) 0.0430(10) Uani 1 1 d
C19 C 0.2788(6) 0.4626(5) 0.4016(4) 0.0472(11) Uani 1 1 d
H19 H 0.384(7) 0.475(5) 0.368(4) 0.062(14) Uiso 1 1 d
C20 C -0.0322(6) 0.6889(5) 0.5657(4) 0.0460(11) Uani 1 1 d
C21 C 0.1970(6) 0.3314(5) 0.3878(4) 0.0469(11) Uani 1 1 d
H21 H 0.246(6) 0.244(4) 0.340(4) 0.042(10) Uiso 1 1 d
C22 C 0.0551(7) 0.8212(5) 0.5775(4) 0.0496(11) Uani 1 1 d
H22 H -0.006(6) 0.901(5) 0.613(4) 0.052(12) Uiso 1 1 d
C23 C 0.2880(7) 0.7208(5) 0.4739(4) 0.0509(12) Uani 1 1 d
H23 H 0.407(6) 0.737(4) 0.437(3) 0.032(9) Uiso 1 1 d
C24 C 0.2142(7) 0.8379(5) 0.5318(4) 0.0552(12) Uani 1 1 d
H24 H 0.267(6) 0.933(5) 0.532(4) 0.046(11) Uiso 1 1 d
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'
N N 0.0061 0.0033 '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
C3 C1 C5 121.9(4) . .
C3 C1 C2 119.1(4) . .
C5 C1 C2 119.1(4) . .
C5 C2 C1 119.9(4) 2_565 .
C1 C3 C4 122.1(4) . .
C1 C3 C6 121.2(4) . .
C4 C3 C6 116.7(4) . .
C2 C5 C1 121.0(4) 2_565 .
N7 C4 C3 177.9(4) . .
N8 C6 C3 178.3(5) . .
C11 C9 C10 120.4(4) . .
C11 C9 C9 119.8(5) . 2_667
C10 C9 C9 119.8(4) . 2_667
C12 C10 C9 118.6(4) . .
C12 C10 C13 122.7(4) . .
C9 C10 C13 118.6(4) . .
C15 C11 C9 118.6(4) . .
C15 C11 C14 122.7(4) . .
C9 C11 C14 118.7(4) . .
C10 C12 C16 120.6(4) . .
C14 C13 C10 121.4(4) 2_667 .
C13 C14 C11 121.6(4) 2_667 .
C16 C15 C11 120.9(4) . .
C15 C16 C12 121.0(4) . .
C20 C17 C18 120.4(4) . .
C20 C17 C17 120.5(5) . 2_566
C18 C17 C17 119.1(5) . 2_566
C23 C18 C19 123.2(4) . .
C23 C18 C17 117.8(4) . .
C19 C18 C17 119.0(4) . .
C21 C19 C18 122.4(4) . .
C22 C20 C17 119.2(4) . .
C22 C20 C21 122.2(4) . 2_566
C17 C20 C21 118.6(4) . 2_566
C19 C21 C20 120.4(4) . 2_566
C20 C22 C24 121.1(5) . .
C24 C23 C18 121.7(4) . .
C23 C24 C22 119.8(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.379(5) .
C1 C5 1.412(6) .
C1 C2 1.445(6) .
C2 C5 1.363(6) 2_565
C3 C4 1.411(6) .
C3 C6 1.441(6) .
N7 C4 1.157(5) .
C5 C2 1.363(6) 2_565
N8 C6 1.144(5) .
C9 C11 1.419(6) .
C9 C10 1.427(6) .
C9 C9 1.428(8) 2_667
C10 C12 1.396(6) .
C10 C13 1.430(6) .
C11 C15 1.406(6) .
C11 C14 1.434(6) .
C12 C16 1.397(6) .
C13 C14 1.347(6) 2_667
C14 C13 1.347(6) 2_667
C15 C16 1.371(6) .
C17 C20 1.418(6) .
C17 C18 1.422(6) .
C17 C17 1.430(8) 2_566
C18 C23 1.401(6) .
C18 C19 1.415(6) .
C19 C21 1.355(6) .
C20 C22 1.385(6) .
C20 C21 1.439(6) 2_566
C21 C20 1.439(6) 2_566
C22 C24 1.389(7) .
C23 C24 1.385(7) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168354143
