#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/41/2224138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224138
loop_
_publ_author_name
'Zhou, Jian-Cheng'
'Zhang, Zheng-Yun'
'Li, Nai-Xu'
'Zhang, Chuan-Ming'
_publ_section_title
;
 (E)-3-[(4-Diethylamino-2-hydroxybenzylidene)amino]benzonitrile
;
_journal_coeditor_code           BX2250
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3251
_journal_paper_doi               10.1107/S1600536809050144
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H19 N3 O'
_chemical_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_chemical_name_systematic
;
(E)-3-[(4-Diethylamino-2-hydroxybenzylidene)amino]benzonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.17(4)
_cell_angle_beta                 79.00(4)
_cell_angle_gamma                64.65(2)
_cell_formula_units_Z            2
_cell_length_a                   8.411(6)
_cell_length_b                   8.519(6)
_cell_length_c                   12.906(9)
_cell_measurement_reflns_used    2426
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4603
_cell_measurement_theta_min      2.2649
_cell_volume                     801.1(10)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       'ω scans'
_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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8686
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.182
_exptl_absorpt_correction_T_min  0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.1000
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0560
_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)+(0.0841P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                2592
_reflns_number_total             3620
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bx2250.cif
_cod_data_source_block           I
_cod_original_cell_volume        801.1(9)
_cod_database_code               2224138
_cod_database_fobs_code          2224138
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C3 0.2014(2) 1.0630(2) 0.37779(12) 0.0428(4) Uani d . 1 . .
H H3A 0.0814 1.1144 0.3988 0.051 Uiso calc R 1 . .
O O1 0.24337(15) 0.87525(17) 0.55059(9) 0.0544(3) Uani d . 1 . .
N N2 0.56035(17) 0.63888(18) 0.59125(10) 0.0456(3) Uani d . 1 . .
C C1 0.4976(2) 0.8526(2) 0.42381(12) 0.0417(4) Uani d . 1 . .
C C4 0.2656(2) 1.1212(2) 0.27203(12) 0.0415(4) Uani d . 1 . .
C C13 0.6447(2) 0.4627(2) 0.76732(12) 0.0455(4) Uani d . 1 . .
H H13A 0.5454 0.5452 0.7974 0.055 Uiso calc R 1 . .
N N1 0.15321(18) 1.24256(19) 0.19656(10) 0.0503(4) Uani d U 1 . .
C C2 0.31405(19) 0.9308(2) 0.45073(11) 0.0396(4) Uani d . 1 . .
C C11 0.6144(2) 0.7100(2) 0.49704(12) 0.0458(4) Uani d . 1 . .
H H11A 0.7348 0.6662 0.4761 0.055 Uiso calc R 1 . .
C C6 0.5599(2) 0.9187(2) 0.31953(12) 0.0485(4) Uani d . 1 . .
H H6A 0.6808 0.8729 0.3003 0.058 Uiso calc R 1 . .
C C12 0.6806(2) 0.4883(2) 0.65573(12) 0.0424(4) Uani d . 1 . .
C C9 0.2167(2) 1.3062(2) 0.08716(13) 0.0547(4) Uani d . 1 . .
H H9A 0.3286 1.3124 0.0891 0.066 Uiso calc R 1 . .
H H9B 0.1333 1.4255 0.0594 0.066 Uiso calc R 1 . .
C C17 0.8278(2) 0.3586(2) 0.61325(13) 0.0493(4) Uani d . 1 . .
H H17A 0.8512 0.3716 0.5387 0.059 Uiso calc R 1 . .
C C5 0.4508(2) 1.0469(2) 0.24531(13) 0.0490(4) Uani d . 1 . .
H H5A 0.4979 1.0858 0.1769 0.059 Uiso calc R 1 . .
C C18 0.7203(2) 0.2892(2) 0.95013(14) 0.0548(4) Uani d . 1 . .
C C14 0.7571(2) 0.3138(2) 0.83397(12) 0.0465(4) Uani d . 1 . .
C C15 0.9066(2) 0.1876(2) 0.79080(14) 0.0511(4) Uani d . 1 . .
H H15A 0.9828 0.0895 0.8358 0.061 Uiso calc R 1 . .
C C7 -0.0392(2) 1.3053(2) 0.21951(13) 0.0533(4) Uani d U 1 . .
H H7A -0.0677 1.2098 0.2678 0.064 Uiso calc R 1 . .
H H7B -0.0928 1.3357 0.1527 0.064 Uiso calc R 1 . .
C C16 0.9387(2) 0.2118(2) 0.68022(14) 0.0524(4) Uani d . 1 . .
H H16A 1.0366 0.1278 0.6502 0.063 Uiso calc R 1 . .
N N3 0.6938(2) 0.2678(3) 1.04170(13) 0.0772(5) Uani d . 1 . .
C C10 0.2415(3) 1.1884(3) 0.01095(15) 0.0798(7) Uani d . 1 . .
H H10A 0.2833 1.2364 -0.0598 0.120 Uiso calc R 1 . .
H H10B 0.1307 1.1837 0.0074 0.120 Uiso calc R 1 . .
H H10C 0.3261 1.0707 0.0370 0.120 Uiso calc R 1 . .
C C8 -0.1160(3) 1.4645(3) 0.27007(17) 0.0716(6) Uani d . 1 . .
H H8A -0.2415 1.4999 0.2842 0.107 Uiso calc R 1 . .
H H8B -0.0912 1.5606 0.2217 0.107 Uiso calc R 1 . .
H H8C -0.0644 1.4348 0.3367 0.107 Uiso calc R 1 . .
H H1A 0.342(3) 0.773(4) 0.5846(19) 0.109(8) Uiso d . 1 . .
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C3 C4 . . 120.82(15) ?
C2 C3 H3A . . 119.6 ?
C4 C3 H3A . . 119.6 ?
C2 O1 H1A . . 104.4(14) ?
C11 N2 C12 . . 120.13(14) ?
C6 C1 C2 . . 116.50(14) ?
C6 C1 C11 . . 121.36(15) ?
C2 C1 C11 . . 122.11(14) ?
N1 C4 C3 . . 121.23(15) ?
N1 C4 C5 . . 121.00(14) ?
C3 C4 C5 . . 117.75(15) ?
C14 C13 C12 . . 120.03(15) ?
C14 C13 H13A . . 120.0 ?
C12 C13 H13A . . 120.0 ?
C4 N1 C9 . . 122.17(15) ?
C4 N1 C7 . . 121.48(14) ?
C9 N1 C7 . . 116.19(13) ?
O1 C2 C3 . . 118.17(14) ?
O1 C2 C1 . . 120.13(14) ?
C3 C2 C1 . . 121.70(14) ?
N2 C11 C1 . . 123.02(15) ?
N2 C11 H11A . . 118.5 ?
C1 C11 H11A . . 118.5 ?
C5 C6 C1 . . 122.87(15) ?
C5 C6 H6A . . 118.6 ?
C1 C6 H6A . . 118.6 ?
C13 C12 C17 . . 118.42(15) ?
C13 C12 N2 . . 118.03(14) ?
C17 C12 N2 . . 123.44(14) ?
N1 C9 C10 . . 112.94(17) ?
N1 C9 H9A . . 109.0 ?
C10 C9 H9A . . 109.0 ?
N1 C9 H9B . . 109.0 ?
C10 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C16 C17 C12 . . 120.98(15) ?
C16 C17 H17A . . 119.5 ?
C12 C17 H17A . . 119.5 ?
C6 C5 C4 . . 120.24(15) ?
C6 C5 H5A . . 119.9 ?
C4 C5 H5A . . 119.9 ?
N3 C18 C14 . . 179.0(2) ?
C13 C14 C15 . . 121.09(15) ?
C13 C14 C18 . . 119.75(16) ?
C15 C14 C18 . . 119.16(16) ?
C16 C15 C14 . . 118.49(16) ?
C16 C15 H15A . . 120.8 ?
C14 C15 H15A . . 120.8 ?
N1 C7 C8 . . 112.48(16) ?
N1 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C15 C16 C17 . . 120.95(16) ?
C15 C16 H16A . . 119.5 ?
C17 C16 H16A . . 119.5 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C3 C2 . 1.379(2) ?
C3 C4 . 1.407(2) ?
C3 H3A . 0.9300 ?
O1 C2 . 1.3616(19) ?
O1 H1A . 0.98(3) ?
N2 C11 . 1.294(2) ?
N2 C12 . 1.410(2) ?
C1 C6 . 1.404(2) ?
C1 C2 . 1.410(2) ?
C1 C11 . 1.428(2) ?
C4 N1 . 1.370(2) ?
C4 C5 . 1.420(2) ?
C13 C14 . 1.390(2) ?
C13 C12 . 1.390(2) ?
C13 H13A . 0.9300 ?
N1 C9 . 1.454(2) ?
N1 C7 . 1.468(2) ?
C11 H11A . 0.9300 ?
C6 C5 . 1.363(2) ?
C6 H6A . 0.9300 ?
C12 C17 . 1.398(2) ?
C9 C10 . 1.516(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C17 C16 . 1.379(2) ?
C17 H17A . 0.9300 ?
C5 H5A . 0.9300 ?
C18 N3 . 1.139(2) ?
C18 C14 . 1.447(2) ?
C14 C15 . 1.396(2) ?
C15 C16 . 1.376(2) ?
C15 H15A . 0.9300 ?
C7 C8 . 1.502(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C16 H16A . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1A N2 . 0.98(3) 1.70(3) 2.607(3) 153(2)
C16 H16A O1 1_645 0.93 2.60 3.504(3) 164
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12550978
2 PubChem 721962
