#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/45/7234543.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_7234543
loop_
_publ_author_name
'Filip Bures'
'Daniel Cvejn'
'Klara Melanova'
'Ludvik Benes'
'Jan Svoboda'
'Vitezslav Zima'
'Oldrich Pytela'
'Tomas Mikysek'
'Zdenka Ruzickova'
'I. V. Kityk'
'Artur Wojciechowski'
'Nasser AlZayed'
_publ_section_title
;
 Effect of intercalation and chromophore arrangement on the linear and
 nonlinear optical properties of model aminopyridine push-pull molecules
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              468
_journal_page_last               478
_journal_paper_doi               10.1039/C5TC03499J
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C15 H12 N4'
_chemical_formula_sum            'C15 H12 N4'
_chemical_formula_weight         248.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 111.714(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7080(4)
_cell_length_b                   15.9311(9)
_cell_length_c                   9.5590(6)
_cell_measurement_reflns_used    10076
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1232.00(12)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10026
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.7337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                2267
_reflns_number_total             2795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-468.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7234543
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N4 N 0.59760(16) 0.07684(8) 0.25833(15) 0.0229(3) Uani 1 1 d . . .
N1 N 0.97517(15) 0.25765(8) 0.43942(14) 0.0189(3) Uani 1 1 d . . .
N3 N 1.42023(15) 0.19303(8) 0.79324(14) 0.0222(3) Uani 1 1 d . . .
C4 C 0.78364(19) 0.46322(9) 0.30023(17) 0.0214(3) Uani 1 1 d . . .
H4 H 0.6812 0.4890 0.2758 0.026 Uiso 1 1 d R . .
C13 C 0.6964(2) 0.07803(10) 0.40406(18) 0.0223(3) Uani 1 1 d . . .
H13 H 0.6792 0.0373 0.4665 0.027 Uiso 1 1 d R . .
C2 C 1.08185(18) 0.38798(9) 0.37725(16) 0.0186(3) Uani 1 1 d . . .
H2 H 1.1865 0.3644 0.4039 0.022 Uiso 1 1 d R . .
C12 C 0.82146(18) 0.13537(9) 0.46826(16) 0.0193(3) Uani 1 1 d . . .
H12 H 0.8861 0.1326 0.5704 0.023 Uiso 1 1 d R . .
C10 C 1.19756(18) 0.29022(9) 0.67788(17) 0.0193(3) Uani 1 1 d . . .
H10 H 1.1493 0.3417 0.6825 0.023 Uiso 1 1 d R . .
C1 C 0.95166(18) 0.34183(9) 0.38861(16) 0.0167(3) Uani 1 1 d . . .
C9 C 1.34459(18) 0.26633(10) 0.78986(17) 0.0205(3) Uani 1 1 d . . .
H9 H 1.3941 0.3038 0.8682 0.025 Uiso 1 1 d R . .
C6 C 1.12376(17) 0.23542(9) 0.55864(16) 0.0171(3) Uani 1 1 d . . .
N2 N 0.90660(17) 0.50840(8) 0.28544(15) 0.0237(3) Uani 1 1 d . . .
C5 C 0.79849(18) 0.38098(9) 0.34930(16) 0.0191(3) Uani 1 1 d . . .
H5 H 0.7083 0.3524 0.3560 0.023 Uiso 1 1 d R . .
C15 C 0.74853(18) 0.19697(10) 0.22567(17) 0.0205(3) Uani 1 1 d . . .
H15 H 0.7630 0.2369 0.1606 0.025 Uiso 1 1 d R . .
C11 C 0.84950(17) 0.19721(9) 0.37777(16) 0.0173(3) Uani 1 1 d . . .
C8 C 1.34587(19) 0.14081(10) 0.67814(18) 0.0225(3) Uani 1 1 d . . .
H8 H 1.3955 0.0891 0.6782 0.027 Uiso 1 1 d R . .
C14 C 0.62647(19) 0.13655(10) 0.17279(17) 0.0224(3) Uani 1 1 d . . .
H14 H 0.5602 0.1375 0.0710 0.027 Uiso 1 1 d R . .
C3 C 1.05266(19) 0.46979(10) 0.32541(17) 0.0213(3) Uani 1 1 d . . .
H3 H 1.1408 0.5000 0.3179 0.026 Uiso 1 1 d R . .
C7 C 1.20004(18) 0.15849(10) 0.55914(17) 0.0206(3) Uani 1 1 d . . .
H7 H 1.1541 0.1201 0.4816 0.025 Uiso 1 1 d 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 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.108
1 0 0 0.120
-1 0 1 0.136
1 0 -1 0.130
0 -1 0 0.066
0 1 0 0.049
1 -1 0 0.119
-1 1 0 0.093
-1 1 -1 0.131
0 0 -1 0.154
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
C14 N4 C13 115.61(13) . .
C11 N1 C1 120.76(12) . .
C11 N1 C6 120.08(12) . .
C1 N1 C6 119.08(12) . .
C9 N3 C8 116.04(13) . .
N2 C4 C5 124.54(14) . .
N2 C4 H4 117.7 . .
C5 C4 H4 117.7 . .
N4 C13 C12 124.71(15) . .
N4 C13 H13 117.6 . .
C12 C13 H13 117.6 . .
C3 C2 C1 118.65(14) . .
C3 C2 H2 120.7 . .
C1 C2 H2 120.7 . .
C13 C12 C11 118.93(14) . .
C13 C12 H12 120.5 . .
C11 C12 H12 120.6 . .
C9 C10 C6 118.44(14) . .
C9 C10 H10 120.7 . .
C6 C10 H10 120.8 . .
C2 C1 C5 118.03(13) . .
C2 C1 N1 120.66(13) . .
C5 C1 N1 121.31(13) . .
N3 C9 C10 124.48(14) . .
N3 C9 H9 117.7 . .
C10 C9 H9 117.8 . .
C10 C6 C7 118.32(14) . .
C10 C6 N1 120.67(13) . .
C7 C6 N1 121.00(13) . .
C3 N2 C4 115.85(13) . .
C4 C5 C1 118.46(14) . .
C4 C5 H5 120.8 . .
C1 C5 H5 120.8 . .
C14 C15 C11 119.08(14) . .
C14 C15 H15 120.4 . .
C11 C15 H15 120.5 . .
C12 C11 C15 117.31(14) . .
C12 C11 N1 120.70(13) . .
C15 C11 N1 121.98(13) . .
N3 C8 C7 124.48(14) . .
N3 C8 H8 117.8 . .
C7 C8 H8 117.8 . .
N4 C14 C15 124.35(14) . .
N4 C14 H14 117.8 . .
C15 C14 H14 117.8 . .
N2 C3 C2 124.45(14) . .
N2 C3 H3 117.7 . .
C2 C3 H3 117.8 . .
C8 C7 C6 118.23(14) . .
C8 C7 H7 120.9 . .
C6 C7 H7 120.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N4 C14 1.337(2) .
N4 C13 1.339(2) .
N1 C11 1.4124(18) .
N1 C1 1.4151(18) .
N1 C6 1.4168(18) .
N3 C9 1.335(2) .
N3 C8 1.340(2) .
C4 N2 1.340(2) .
C4 C5 1.381(2) .
C4 H4 0.9301 .
C13 C12 1.380(2) .
C13 H13 0.9299 .
C2 C3 1.384(2) .
C2 C1 1.389(2) .
C2 H2 0.9300 .
C12 C11 1.391(2) .
C12 H12 0.9300 .
C10 C9 1.384(2) .
C10 C6 1.390(2) .
C10 H10 0.9302 .
C1 C5 1.392(2) .
C9 H9 0.9300 .
C6 C7 1.393(2) .
N2 C3 1.335(2) .
C5 H5 0.9300 .
C15 C14 1.384(2) .
C15 C11 1.393(2) .
C15 H15 0.9300 .
C8 C7 1.385(2) .
C8 H8 0.9299 .
C14 H14 0.9300 .
C3 H3 0.9302 .
C7 H7 0.9301 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 54183160
