#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/54/4515437.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_4515437
loop_
_publ_author_name
'Jin, Jianqun'
'Long, Guankui'
'Gao, Yongqian'
'Zhang, Jing'
'Ou, Changjin'
'Zhu, Caixia'
'Xu, Haixiao'
'Zhao, Jianfeng'
'Zhang, Mingtao'
'Huang, Wei'
_publ_section_title
;
 Supramolecular Design of Donor-Acceptor Complexes via Heteroatom
 Replacement toward Structure and Electrical Transporting Property
 Tailoring.
;
_journal_issue                   1
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              1109
_journal_page_last               1116
_journal_paper_doi               10.1021/acsami.8b16561
_journal_volume                  11
_journal_year                    2019
_chemical_formula_sum            'C26 H13 N6'
_chemical_formula_weight         409.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.311(6)
_cell_length_b                   9.744(7)
_cell_length_c                   28.77(2)
_cell_measurement_reflns_used    1115
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.106
_cell_measurement_theta_min      2.525
_cell_volume                     2048(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10098
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.525
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.101873
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0496
_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)+(0.0643P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1748
_reflns_number_total             3608
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am8b16561_si_003.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4515437
_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   0.984
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N5 N 0.8962(3) 0.4801(2) 0.45909(6) 0.0565(5) Uani 1 1 d . .
N6 N 1.0721(3) 0.6422(2) 0.42072(6) 0.0596(6) Uani 1 1 d . .
C14 C 1.0336(3) 0.5701(2) 0.46158(7) 0.0533(6) Uani 1 1 d . .
C9 C 0.3142(3) 0.1518(3) 0.63661(7) 0.0542(6) Uani 1 1 d . .
C4 C 0.4388(3) 0.4226(3) 0.62321(7) 0.0540(6) Uani 1 1 d . .
C13 C 0.8635(3) 0.4105(2) 0.49756(8) 0.0566(6) Uani 1 1 d . .
H13 H 0.7688 0.3468 0.4971 0.068 Uiso 1 1 calc R U
C8 C 0.3676(3) 0.1988(3) 0.59139(8) 0.0596(7) Uani 1 1 d . .
H8 H 0.3619 0.1387 0.5663 0.072 Uiso 1 1 calc R U
N2 N 0.6000(3) 0.6453(2) 0.53810(7) 0.0822(7) Uani 1 1 d . .
C6 C 0.4252(3) 0.3274(3) 0.58518(7) 0.0578(7) Uani 1 1 d . .
H6 H 0.4571 0.3557 0.5557 0.069 Uiso 1 1 calc R U
C10 C 0.2510(3) 0.0212(3) 0.64245(8) 0.0602(7) Uani 1 1 d . .
C3 C 0.4965(3) 0.5544(3) 0.61719(7) 0.0579(7) Uani 1 1 d . .
C5 C 0.3888(3) 0.3746(3) 0.66829(7) 0.0598(7) Uani 1 1 d . .
H5 H 0.3985 0.4339 0.6936 0.072 Uiso 1 1 calc R U
C15 C 1.1301(3) 0.7795(3) 0.41800(8) 0.0631(7) Uani 1 1 d . .
C7 C 0.3288(3) 0.2469(3) 0.67467(7) 0.0605(7) Uani 1 1 d . .
H7 H 0.2960 0.2191 0.7042 0.073 Uiso 1 1 calc R U
C2 C 0.5524(4) 0.6050(3) 0.57306(9) 0.0632(7) Uani 1 1 d . .
C26 C 1.0663(3) 0.5868(3) 0.37578(8) 0.0625(7) Uani 1 1 d . .
N4 N 0.2368(4) -0.1544(3) 0.57573(8) 0.0939(8) Uani 1 1 d . .
C20 C 1.1629(3) 0.8099(3) 0.37137(9) 0.0685(8) Uani 1 1 d . .
N1 N 0.5097(4) 0.7315(3) 0.68307(8) 0.0982(9) Uani 1 1 d . .
C12 C 0.2425(4) -0.0768(3) 0.60534(9) 0.0699(8) Uani 1 1 d . .
C1 C 0.5040(4) 0.6517(3) 0.65402(9) 0.0684(8) Uani 1 1 d . .
C21 C 1.1227(3) 0.6888(3) 0.34476(8) 0.0713(8) Uani 1 1 d . .
N3 N 0.1318(4) -0.0632(3) 0.72041(8) 0.1033(9) Uani 1 1 d . .
C16 C 1.1492(4) 0.8775(3) 0.45272(10) 0.0750(8) Uani 1 1 d . .
H16 H 1.1237 0.8571 0.4834 0.090 Uiso 1 1 calc R U
C25 C 1.0197(4) 0.4560(3) 0.36076(8) 0.0744(8) Uani 1 1 d . .
H25 H 0.9837 0.3887 0.3815 0.089 Uiso 1 1 calc R U
C11 C 0.1863(4) -0.0265(3) 0.68584(9) 0.0733(8) Uani 1 1 d . .
C19 C 1.2214(4) 0.9433(4) 0.36013(12) 0.0883(10) Uani 1 1 d . .
H19 H 1.2448 0.9663 0.3295 0.106 Uiso 1 1 calc R U
C22 C 1.1297(4) 0.6581(4) 0.29733(10) 0.0936(11) Uani 1 1 d . .
H22 H 1.1664 0.7242 0.2762 0.112 Uiso 1 1 calc R U
C23 C 1.0822(4) 0.5305(5) 0.28268(10) 0.1031(12) Uani 1 1 d . .
H23 H 1.0855 0.5100 0.2511 0.124 Uiso 1 1 calc R U
C17 C 1.2071(4) 1.0058(3) 0.44007(12) 0.0932(9) Uani 1 1 d . .
H17 H 1.2224 1.0729 0.4629 0.112 Uiso 1 1 calc R U
C24 C 1.0288(4) 0.4293(4) 0.31342(9) 0.0945(10) Uani 1 1 d . .
H24 H 0.9987 0.3424 0.3022 0.113 Uiso 1 1 calc R U
C18 C 1.2434(5) 1.0384(4) 0.39472(14) 0.1014(11) Uani 1 1 d . .
H18 H 1.2834 1.1263 0.3876 0.122 Uiso 1 1 calc R U
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
C13 N5 C14 116.6(2) . .
C26 N6 C14 125.4(2) . .
C26 N6 C15 108.4(2) . .
C14 N6 C15 126.2(2) . .
N5 C14 C13 121.4(2) . 3_766
N5 C14 N6 117.1(2) . .
C13 C14 N6 121.5(2) 3_766 .
C10 C9 C7 121.6(2) . .
C10 C9 C8 120.6(2) . .
C7 C9 C8 117.8(3) . .
C3 C4 C6 121.7(2) . .
C3 C4 C5 120.7(2) . .
C6 C4 C5 117.6(3) . .
N5 C13 C14 122.0(2) . 3_766
C6 C8 C9 120.9(2) . .
C8 C6 C4 121.3(2) . .
C9 C10 C11 122.3(2) . .
C9 C10 C12 122.4(2) . .
C11 C10 C12 115.3(2) . .
C4 C3 C1 122.5(2) . .
C4 C3 C2 122.3(2) . .
C1 C3 C2 115.2(2) . .
C7 C5 C4 121.5(2) . .
C16 C15 C20 121.8(3) . .
C16 C15 N6 129.7(2) . .
C20 C15 N6 108.4(2) . .
C5 C7 C9 120.9(2) . .
N2 C2 C3 178.9(3) . .
C25 C26 N6 130.0(2) . .
C25 C26 C21 121.8(3) . .
N6 C26 C21 108.2(3) . .
C15 C20 C19 118.5(3) . .
C15 C20 C21 107.4(3) . .
C19 C20 C21 134.1(3) . .
N4 C12 C10 179.5(3) . .
N1 C1 C3 178.9(3) . .
C22 C21 C26 119.2(3) . .
C22 C21 C20 133.1(3) . .
C26 C21 C20 107.6(2) . .
C17 C16 C15 117.5(3) . .
C26 C25 C24 117.3(3) . .
N3 C11 C10 178.7(3) . .
C18 C19 C20 119.2(3) . .
C23 C22 C21 118.8(3) . .
C22 C23 C24 121.9(3) . .
C16 C17 C18 122.1(3) . .
C23 C24 C25 120.9(3) . .
C19 C18 C17 120.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N5 C13 1.326(3) .
N5 C14 1.333(3) .
N6 C26 1.400(3) .
N6 C14 1.406(3) .
N6 C15 1.406(3) .
C14 C13 1.387(3) 3_766
C9 C10 1.366(3) .
C9 C7 1.436(3) .
C9 C8 1.445(3) .
C4 C3 1.364(3) .
C4 C6 1.436(3) .
C4 C5 1.437(3) .
C13 C14 1.387(3) 3_766
C8 C6 1.335(3) .
N2 C2 1.144(3) .
C10 C11 1.427(4) .
C10 C12 1.432(4) .
C3 C1 1.421(4) .
C3 C2 1.434(3) .
C5 C7 1.334(3) .
C15 C16 1.385(3) .
C15 C20 1.402(3) .
C26 C25 1.385(4) .
C26 C21 1.407(3) .
N4 C12 1.139(3) .
C20 C19 1.409(4) .
C20 C21 1.432(4) .
N1 C1 1.141(3) .
C21 C22 1.400(4) .
N3 C11 1.141(3) .
C16 C17 1.373(4) .
C25 C24 1.390(3) .
C19 C18 1.365(4) .
C22 C23 1.355(4) .
C23 C24 1.389(4) .
C17 C18 1.377(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345699
