#------------------------------------------------------------------------------
#$Date: 2020-06-04 03:53:36 +0300 (Thu, 04 Jun 2020) $
#$Revision: 252587 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/76/4517662.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_4517662
loop_
_publ_author_name
'Uekusa, Tomoki'
'Sato, Ryonosuke'
'Yoo, Dongho'
'Kawamoto, Tadashi'
'Mori, Takehiko'
_publ_section_title
;
 Transistor Characteristics of Charge-Transfer Complexes Observed across a
 Neutral-Ionic Transition.
;
_journal_issue                   21
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              24174
_journal_page_last               24183
_journal_paper_doi               10.1021/acsami.0c03898
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C14 H8 N4, C16 H20 N2 '
_chemical_formula_sum            'C30 H28 N6'
_chemical_formula_weight         472.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           58
_space_group_name_Hall           '-P 2 2n'
_space_group_name_H-M_alt        'P n n m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   22.0548(5)
_cell_length_b                   8.5264(2)
_cell_length_c                   6.69588(17)
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    274
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      4.01
_cell_volume                     1259.15(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      274
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0445
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5938
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.686
_diffrn_reflns_theta_min         4.009
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             500.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1232P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.2204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                560
_reflns_number_total             1202
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            am0c03898_si_002.cif
_cod_data_source_block           20190426
_cod_depositor_comments          'Adding full bibliography for 4517662.cif.'
_cod_database_code               4517662
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,+Z
3 1/2+X,1/2-Y,1/2-Z
4 1/2-X,1/2+Y,1/2-Z
5 -X,-Y,-Z
6 +X,+Y,-Z
7 -1/2-X,-1/2+Y,-1/2+Z
8 -1/2+X,-1/2-Y,-1/2+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
N1 N 0.21557(13) 0.8403(4) 0.500000 0.0725(12) Uani 1 2 d S T P . .
H1A H 0.225518 0.742825 0.500000 0.087 Uiso 1 2 calc R U P . .
H1B H 0.243241 0.911403 0.500000 0.087 Uiso 1 2 calc R U P . .
N2 N 0.3516(2) 0.0875(5) 0.500000 0.0947(16) Uani 1 2 d S T P . .
N3 N 0.28153(18) 0.5327(5) 0.500000 0.0877(14) Uani 1 2 d S T P . .
C1 C 0.15562(17) 0.8825(5) 0.500000 0.0549(12) Uani 1 2 d S T P . .
C2 C 0.10911(18) 0.7692(5) 0.500000 0.0533(12) Uani 1 2 d S T P . .
C3 C 0.13984(18) 1.0448(5) 0.500000 0.0571(12) Uani 1 2 d S T P . .
C4 C 0.05010(17) 0.8176(5) 0.500000 0.0529(11) Uani 1 2 d S T P . .
H4 H 0.020017 0.741227 0.500000 0.063 Uiso 1 2 calc R U P . .
C5 C 0.07979(17) 1.0853(5) 0.500000 0.0569(12) Uani 1 2 d S T P . .
H5 H 0.069995 1.191346 0.500000 0.068 Uiso 1 2 calc R U P . .
C6 C 0.03191(16) 0.9758(5) 0.500000 0.0519(11) Uani 1 2 d S T P . .
C7 C 0.1252(2) 0.5956(5) 0.500000 0.0701(14) Uani 1 2 d S T P . .
H7A H 0.088690 0.534346 0.500000 0.105 Uiso 1 2 calc R U P . .
H7B H 0.148548 0.571500 0.617063 0.105 Uiso 0.5 1 calc R U P . .
H7C H 0.148548 0.571500 0.382937 0.105 Uiso 0.5 1 calc R U P . .
C8 C 0.18922(19) 1.1687(6) 0.500000 0.0730(14) Uani 1 2 d S T P . .
H8A H 0.171062 1.270999 0.500000 0.109 Uiso 1 2 calc R U P . .
H8B H 0.213924 1.156711 0.382937 0.109 Uiso 0.5 1 calc R U P . .
H8C H 0.213924 1.156711 0.617063 0.109 Uiso 0.5 1 calc R U P . .
C9 C 0.36751(19) 0.2148(6) 0.500000 0.0633(13) Uani 1 2 d S T P . .
C10 C 0.3276(2) 0.4697(6) 0.500000 0.0642(13) Uani 1 2 d S T P . .
C11 C 0.38147(17) 0.3786(5) 0.500000 0.0585(13) Uani 1 2 d S T P . .
C12 C 0.43996(16) 0.4398(5) 0.500000 0.0503(11) Uani 1 2 d S T P A .
C13 C 0.49180(17) 0.3367(5) 0.500000 0.0599(13) Uani 1 2 d S T P . .
H13 H 0.485923 0.228732 0.500000 0.072 Uiso 0.589(7) 2 calc R U P A 1
C15A C 0.5967(3) 0.2617(9) 0.500000 0.075(3) Uani 0.589(7) 2 d S T P A 1
H15A H 0.576571 0.161891 0.500000 0.113 Uiso 0.589(7) 2 calc R U P A 1
H15B H 0.621597 0.270468 0.617063 0.113 Uiso 0.294(4) 1 calc R U P A 1
H15C H 0.621597 0.270468 0.382937 0.113 Uiso 0.294(4) 1 calc R U P A 1
C15B C 0.4921(4) 0.1541(10) 0.500000 0.059(3) Uani 0.411(7) 2 d S T P A 2
H15D H 0.451130 0.116087 0.500000 0.089 Uiso 0.411(7) 2 calc R U P A 2
H15E H 0.512687 0.116779 0.382937 0.089 Uiso 0.206(4) 1 calc R U P A 2
H15F H 0.512688 0.116779 0.617063 0.089 Uiso 0.206(4) 1 calc R U P A 2
C14 C 0.54872(18) 0.3948(5) 0.500000 0.0560(12) Uani 1 2 d S T P A .
H14 H 0.581369 0.325824 0.500000 0.067 Uiso 0.411(7) 2 calc R U P A 2
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
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(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
_geom_angle_publ_flag
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C1 C2 121.5(4) . . ?
N1 C1 C3 119.3(4) . . ?
C2 C1 C3 119.2(4) . . ?
C4 C2 C1 119.1(4) . . ?
C4 C2 C7 121.1(4) . . ?
C1 C2 C7 119.8(4) . . ?
C5 C3 C1 118.7(4) . . ?
C5 C3 C8 121.3(4) . . ?
C1 C3 C8 120.0(4) . . ?
C2 C4 C6 124.2(4) . . ?
C2 C4 H4 117.9 . . ?
C6 C4 H4 117.9 . . ?
C3 C5 C6 123.9(4) . . ?
C3 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C4 C6 C5 114.9(3) . . ?
C4 C6 C6 122.9(5) . 5_576 ?
C5 C6 C6 122.2(5) . 5_576 ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C11 174.5(5) . . ?
N3 C10 C11 174.6(5) . . ?
C12 C11 C10 124.8(4) . . ?
C12 C11 C9 124.5(4) . . ?
C10 C11 C9 110.8(4) . . ?
C11 C12 C14 122.1(4) . 5_666 ?
C11 C12 C13 120.4(4) . . ?
C14 C12 C13 117.5(3) 5_666 . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 C15B 111.3(5) . . ?
C12 C13 C15B 127.8(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C14 C15A H15A 109.5 . . ?
C14 C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14 C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C13 C15B H15D 109.5 . . ?
C13 C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C13 C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C13 C14 C12 121.6(4) . 5_666 ?
C13 C14 C15A 111.5(5) . . ?
C12 C14 C15A 127.0(4) 5_666 . ?
C13 C14 H14 119.2 . . ?
C12 C14 H14 119.2 5_666 . ?
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
N1 C1 1.370(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C9 1.140(6) . ?
N3 C10 1.150(5) . ?
C1 C2 1.409(5) . ?
C1 C3 1.427(5) . ?
C2 C4 1.365(5) . ?
C2 C7 1.522(5) . ?
C3 C5 1.369(5) . ?
C3 C8 1.517(6) . ?
C4 C6 1.407(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(5) . ?
C5 H5 0.9300 . ?
C6 C6 1.467(7) 5_576 ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C11 1.430(6) . ?
C10 C11 1.419(6) . ?
C11 C12 1.392(5) . ?
C12 C14 1.431(5) 5_666 ?
C12 C13 1.442(5) . ?
C13 C14 1.350(5) . ?
C13 C15B 1.557(9) . ?
C13 H13 0.9300 . ?
C15A C14 1.552(8) . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C14 H14 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A N3 . . . 2.999(5) 0.860 2.176 160.2 no
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
N1 C1 C2 C4 180.0 . . . . ?
C3 C1 C2 C4 0.0 . . . . ?
N1 C1 C2 C7 0.0 . . . . ?
C3 C1 C2 C7 180.0 . . . . ?
N1 C1 C3 C5 180.0 . . . . ?
C2 C1 C3 C5 0.0 . . . . ?
N1 C1 C3 C8 0.0 . . . . ?
C2 C1 C3 C8 180.0 . . . . ?
C1 C2 C4 C6 0.0 . . . . ?
C7 C2 C4 C6 180.0 . . . . ?
C1 C3 C5 C6 0.0 . . . . ?
C8 C3 C5 C6 180.0 . . . . ?
C2 C4 C6 C5 0.0 . . . . ?
C2 C4 C6 C6 180.0 . . . 5_576 ?
C3 C5 C6 C4 0.0 . . . . ?
C3 C5 C6 C6 180.0 . . . 5_576 ?
C10 C11 C12 C14 0.0 . . . 5_666 ?
C9 C11 C12 C14 180.0 . . . 5_666 ?
C10 C11 C12 C13 180.0 . . . . ?
C9 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 180.0 . . . . ?
C14 C12 C13 C14 0.0 5_666 . . . ?
C11 C12 C13 C15B 0.0 . . . . ?
C14 C12 C13 C15B 180.0 5_666 . . . ?
C12 C13 C14 C12 0.0 . . . 5_666 ?
C15B C13 C14 C12 180.0 . . . 5_666 ?
C12 C13 C14 C15A 180.0 . . . . ?
