#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/41/1554134.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_1554134
loop_
_publ_author_name
'Sanada, Ryo'
'Yoo, Dongho'
'Sato, Ryonosuke'
'Iijima, Kodai'
'Kawamoto, Tadashi'
'Mori, Takehiko'
_publ_section_title
;
 Ambipolar Transistor Properties of Charge-Transfer Complexes Containing
 Perylene and Dicyanoquinonediimines
;
_journal_issue                   19
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              12088
_journal_paper_doi               10.1021/acs.jpcc.9b01453
_journal_volume                  123
_journal_year                    2019
_chemical_formula_moiety         'C20 H12, C8 H2 Cl2 N4'
_chemical_formula_sum            'C28 H14 Cl2 N4'
_chemical_formula_weight         477.35
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                67.9300(8)
_cell_angle_beta                 77.0956(8)
_cell_angle_gamma                87.4287(9)
_cell_formula_units_Z            1
_cell_length_a                   7.33915(13)
_cell_length_b                   8.13493(15)
_cell_length_c                   9.97271(18)
_cell_measurement_reflns_used    6039
_cell_measurement_temperature    274
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      4.91
_cell_volume                     537.339(17)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      274
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6348
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.922
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             244.00
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1931
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0592P)²+0.0880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                1744
_reflns_number_total             1931
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jp9b01453_si_002.cif
_cod_data_source_block           20180115
_cod_original_cell_volume        537.339(18)
_cod_database_code               1554134
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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
_atom_site_refinement_flags
Cl1 Cl 0.71603(6) 0.76485(5) 0.19084(4) 0.04705(18) Uani 1.0 2 d .
N1 N 0.55798(19) 0.41418(18) 0.25421(15) 0.0410(4) Uani 1.0 2 d .
N2 N 0.4593(3) 0.1219(3) 0.2626(2) 0.0626(5) Uani 1.0 2 d .
C1 C 0.2629(3) 0.7410(3) 0.10795(19) 0.0533(5) Uani 1.0 2 d .
C2 C 0.2062(3) 0.5897(3) 0.09742(18) 0.0520(5) Uani 1.0 2 d .
C3 C 0.0961(3) 0.4560(3) 0.22163(17) 0.0421(4) Uani 1.0 2 d .
C4 C 0.0325(3) 0.3005(3) 0.2112(2) 0.0495(5) Uani 1.0 2 d .
C5 C -0.0747(3) 0.1734(3) 0.3319(3) 0.0497(5) Uani 1.0 2 d .
C6 C -0.1237(3) 0.1936(3) 0.4687(2) 0.0439(4) Uani 1.0 2 d .
C7 C -0.0635(2) 0.3423(2) 0.48628(17) 0.0356(4) Uani 1.0 2 d .
C8 C 0.0480(2) 0.4779(2) 0.36078(16) 0.0351(4) Uani 1.0 2 d .
C9 C 0.1118(2) 0.6359(2) 0.37024(16) 0.0364(4) Uani 1.0 2 d .
C10 C 0.2157(3) 0.7641(3) 0.24364(19) 0.0460(4) Uani 1.0 2 d .
C11 C 0.5691(3) 0.6686(2) 0.48025(17) 0.0375(4) Uani 1.0 2 d .
C12 C 0.5966(2) 0.6230(2) 0.36150(16) 0.0354(4) Uani 1.0 2 d .
C13 C 0.5277(2) 0.4504(2) 0.37405(17) 0.0353(4) Uani 1.0 2 d .
C14 C 0.5000(3) 0.2545(3) 0.26568(18) 0.0452(4) Uani 1.0 2 d .
H1 H 0.3332 0.8292 0.0246 0.0639 Uiso 1.0 2 calc R
H2 H 0.2406 0.5746 0.0073 0.0624 Uiso 1.0 2 calc R
H4 H 0.0643 0.2850 0.1212 0.0594 Uiso 1.0 2 calc R
H5 H -0.1159 0.0721 0.3234 0.0597 Uiso 1.0 2 calc R
H6 H -0.1980 0.1056 0.5495 0.0526 Uiso 1.0 2 calc R
H10 H 0.2551 0.8682 0.2488 0.0552 Uiso 1.0 2 calc R
H11 H 0.6134 0.7795 0.4687 0.0449 Uiso 1.0 2 calc R
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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C13 N1 C14 118.45(13) yes . .
C2 C1 C10 120.32(15) yes . .
C1 C2 C3 120.74(19) yes . .
C2 C3 C4 121.28(18) yes . .
C2 C3 C8 119.36(19) yes . .
C4 C3 C8 119.36(13) yes . .
C3 C4 C5 120.5(2) yes . .
C4 C5 C6 120.7(2) yes . .
C5 C6 C7 121.40(14) yes . .
C6 C7 C8 118.79(17) yes . .
C6 C7 C9 121.97(13) yes . 2_566
C8 C7 C9 119.24(16) yes . 2_566
C3 C8 C7 119.21(17) yes . .
C3 C8 C9 119.04(13) yes . .
C7 C8 C9 121.76(16) yes . .
C7 C9 C8 119.00(12) yes 2_566 .
C7 C9 C10 122.11(17) yes 2_566 .
C8 C9 C10 118.88(17) yes . .
C1 C10 C9 121.63(19) yes . .
C12 C11 C13 121.70(16) yes . 2_666
Cl1 C12 C11 120.70(13) yes . .
Cl1 C12 C13 118.23(13) yes . .
C11 C12 C13 121.06(13) yes . .
N1 C13 C11 124.62(16) yes . 2_666
N1 C13 C12 118.15(12) yes . .
C11 C13 C12 117.23(16) yes 2_666 .
N1 C14 N2 173.85(18) yes . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
Cl1 C12 1.7163(13) yes .
N1 C13 1.306(3) yes .
N1 C14 1.340(3) yes .
N2 C14 1.146(3) yes .
C1 C2 1.364(4) yes .
C1 C10 1.401(3) yes .
C2 C3 1.411(2) yes .
C3 C4 1.415(3) yes .
C3 C8 1.430(3) yes .
C4 C5 1.361(3) yes .
C5 C6 1.401(4) yes .
C6 C7 1.389(3) yes .
C7 C8 1.4279(18) yes .
C7 C9 1.471(3) yes 2_566
C8 C9 1.430(3) yes .
C9 C10 1.3839(19) yes .
C11 C12 1.341(3) yes .
C11 C13 1.4480(19) yes 2_666
C12 C13 1.465(3) yes .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304243
