#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/41/1554136.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_1554136
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         'C14 H8 N4, C16 H10'
_chemical_formula_sum            'C30 H18 N4'
_chemical_formula_weight         434.50
_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                105.15(7)
_cell_angle_beta                 101.29(2)
_cell_angle_gamma                95.70(8)
_cell_formula_units_Z            1
_cell_length_a                   6.896(3)
_cell_length_b                   9.01(3)
_cell_length_c                   9.5168(18)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      17.36
_cell_measurement_theta_min      15.65
_cell_volume                     552.6(19)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        WinAFC
_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      295
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3546
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_standards_decay_%        -0.462
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             226.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0768P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1974
_reflns_number_gt                1172
_reflns_number_total             2946
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jp9b01453_si_002.cif
_cod_data_source_block           Cytidine_(Rigaku_Master_fo
_cod_original_cell_volume        552.6(14)
_cod_database_code               1554136
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
N1 N 0.3716(6) -0.0372(3) 0.2996(4) 0.0882(10) Uani 1.0 2 d .
N2 N 0.3040(5) 0.1969(3) -0.0289(3) 0.0794(9) Uani 1.0 2 d .
C1 C -0.0257(5) 0.2431(4) 0.5603(5) 0.0714(10) Uani 1.0 2 d .
C2 C -0.0558(4) 0.2823(3) 0.4209(4) 0.0570(8) Uani 1.0 2 d .
C3 C -0.1100(6) 0.1730(4) 0.2823(5) 0.0805(11) Uani 1.0 2 d .
C4 C -0.1359(6) 0.2162(5) 0.1572(5) 0.0906(13) Uani 1.0 2 d .
C5 C -0.1114(5) 0.3690(5) 0.1578(4) 0.0789(11) Uani 1.0 2 d .
C6 C -0.0555(4) 0.4892(4) 0.2969(3) 0.0571(8) Uani 1.0 2 d .
C7 C -0.0250(5) 0.6502(5) 0.3098(5) 0.0722(10) Uani 1.0 2 d .
C8 C -0.0276(4) 0.4435(3) 0.4289(3) 0.0440(7) Uani 1.0 2 d .
C9 C 0.5706(5) 0.4445(3) 0.7963(3) 0.0490(7) Uani 1.0 2 d .
C10 C 0.5361(4) 0.4750(3) 0.6457(3) 0.0384(6) Uani 1.0 2 d .
C11 C 0.4861(4) 0.3547(3) 0.5212(3) 0.0390(6) Uani 1.0 2 d .
C12 C 0.4466(4) 0.3684(3) 0.3713(3) 0.0360(6) Uani 1.0 2 d .
C13 C 0.3948(4) 0.2334(3) 0.2540(3) 0.0434(7) Uani 1.0 2 d .
C14 C 0.3829(5) 0.0841(3) 0.2826(3) 0.0572(8) Uani 1.0 2 d .
C15 C 0.3473(5) 0.2195(3) 0.0980(4) 0.0543(7) Uani 1.0 2 d .
H1 H -0.0429 0.1388 0.5579 0.0857 Uiso 1.0 2 calc R
H3 H -0.1286 0.0677 0.2762 0.0966 Uiso 1.0 2 calc R
H4 H -0.1722 0.1394 0.0657 0.1087 Uiso 1.0 2 calc R
H5 H -0.1310 0.3946 0.0680 0.0947 Uiso 1.0 2 calc R
H7 H -0.0415 0.6814 0.2231 0.0866 Uiso 1.0 2 calc R
H9A H 0.5425 0.3345 0.7828 0.0588 Uiso 1.0 2 calc R
H9B H 0.4837 0.4965 0.8531 0.0588 Uiso 1.0 2 calc R
H9C H 0.7075 0.4829 0.8489 0.0588 Uiso 1.0 2 calc R
H11 H 0.4762 0.2549 0.5324 0.0468 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 0.0033 0.0016
;
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 0.0061 0.0033
;
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
C2 C1 C7 122.1(4) yes . 2_566
C1 C2 C3 123.6(4) yes . .
C1 C2 C8 117.4(3) yes . .
C3 C2 C8 119.0(4) yes . .
C2 C3 C4 120.9(4) yes . .
C3 C4 C5 122.7(4) yes . .
C4 C5 C6 119.7(4) yes . .
C5 C6 C7 124.2(4) yes . .
C5 C6 C8 117.6(4) yes . .
C7 C6 C8 118.3(3) yes . .
C1 C7 C6 122.3(4) yes 2_566 .
C2 C8 C6 120.1(3) yes . .
C2 C8 C8 119.3(3) yes . 2_566
C6 C8 C8 120.7(3) yes . 2_566
C9 C10 C11 119.5(3) yes . .
C9 C10 C12 122.69(19) yes . 2_666
C11 C10 C12 117.8(3) yes . 2_666
C10 C11 C12 124.8(3) yes . .
C10 C12 C11 117.36(19) yes 2_666 .
C10 C12 C13 124.5(3) yes 2_666 .
C11 C12 C13 118.1(3) yes . .
C12 C13 C14 120.3(3) yes . .
C12 C13 C15 127.6(3) yes . .
C14 C13 C15 112.2(2) yes . .
N1 C14 C13 177.4(3) yes . .
N2 C15 C13 174.9(3) 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
N1 C14 1.143(5) yes .
N2 C15 1.143(4) yes .
C1 C2 1.442(6) yes .
C1 C7 1.310(5) yes 2_566
C2 C3 1.380(5) yes .
C2 C8 1.426(5) yes .
C3 C4 1.333(7) yes .
C4 C5 1.369(7) yes .
C5 C6 1.429(5) yes .
C6 C7 1.414(6) yes .
C6 C8 1.405(5) yes .
C8 C8 1.419(4) yes 2_566
C9 C10 1.508(4) yes .
C10 C11 1.338(4) yes .
C10 C12 1.458(5) yes 2_666
C11 C12 1.439(4) yes .
C12 C13 1.378(4) yes .
C13 C14 1.439(5) yes .
C13 C15 1.426(4) yes .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304245
