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#$Date: 2023-06-07 10:57:29 +0300 (Wed, 07 Jun 2023) $
#$Revision: 284396 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107305.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_8107305
loop_
_publ_author_name
'Setshedi, Itumeleng B.'
'Lemmerer, Andreas'
'Smith, Mark G.'
_publ_section_title
;
 The crystal structure of
 N′-[bis(2-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide,
 C19H15N3O3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1105
_journal_page_last               1107
_journal_paper_doi               10.1515/ncrs-2022-0356
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C19 H15 N3 O3'
_chemical_formula_sum            'C19 H15 N3 O3'
_chemical_formula_weight         333.34
_chemical_name_systematic
;
N'-[bis(2-hydroxyphenyl)methylidene]pyridine-4-carbohydrazide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 115.7390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.6917(6)
_cell_length_b                   10.1392(3)
_cell_length_c                   16.9544(5)
_cell_measurement_reflns_used    8181
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.19
_cell_measurement_wavelength     0.71073
_cell_volume                     3204.07(17)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016) [1]'
_computing_data_collection       'APEX3 (Bruker, 2016) [1]'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016) [1]'
_computing_molecular_graphics
'Ortep for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006) [4]'
_computing_publication_material
'WinGX publication routines (Farrugia, 2012) [5]'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015) [3]'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015) [2]'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.995
_diffrn_reflns_theta_min         2.185
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016) [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0473P)²+2.1225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0
_reflns_number_gt                3340
_reflns_number_total             3872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0356_suppl.cif
_cod_data_source_block           13ms_mgs129_p
_cod_original_cell_volume        3204.07(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8107305
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.18530(6) 0.48217(11) 0.00875(7) 0.0229(2) Uani 1 1 d . . . . .
C2 C -0.18090(7) 0.59801(12) -0.03244(8) 0.0313(3) Uani 1 1 d . . . . .
H2A H -0.135895 0.629967 -0.02665 0.038 Uiso 1 1 calc R U . . .
C3 C -0.24367(7) 0.66582(13) -0.08216(8) 0.0357(3) Uani 1 1 d . . . . .
H3A H -0.240643 0.744564 -0.110745 0.043 Uiso 1 1 calc R U . . .
C4 C -0.31206(6) 0.51342(12) -0.05324(8) 0.0309(3) Uani 1 1 d . . . . .
H4 H -0.357842 0.483541 -0.060549 0.037 Uiso 1 1 calc R U . . .
C5 C -0.25246(6) 0.43823(11) -0.00302(8) 0.0266(2) Uani 1 1 d . . . . .
H5 H -0.257386 0.358104 0.022907 0.032 Uiso 1 1 calc R U . . .
C6 C -0.12008(6) 0.39996(11) 0.06116(7) 0.0222(2) Uani 1 1 d . . . . .
C7 C 0.06093(5) 0.48892(10) 0.18322(7) 0.0188(2) Uani 1 1 d . . . . .
C8 C 0.05681(5) 0.63347(10) 0.16316(7) 0.0192(2) Uani 1 1 d . . . . .
C9 C 0.03440(6) 0.67069(11) 0.07594(8) 0.0273(2) Uani 1 1 d . . . . .
H9 H 0.023726 0.604289 0.032532 0.033 Uiso 1 1 calc R U . . .
C10 C 0.02733(7) 0.80184(12) 0.05115(8) 0.0352(3) Uani 1 1 d . . . . .
H10 H 0.012886 0.825523 -0.008337 0.042 Uiso 1 1 calc R U . . .
C11 C 0.04170(7) 0.89814(12) 0.11462(9) 0.0341(3) Uani 1 1 d . . . . .
H11 H 0.036033 0.988493 0.09816 0.041 Uiso 1 1 calc R U . . .
C12 C 0.06415(6) 0.86438(10) 0.20145(8) 0.0261(2) Uani 1 1 d . . . . .
H12 H 0.0739 0.931475 0.244231 0.031 Uiso 1 1 calc R U . . .
C13 C 0.07259(5) 0.73183(10) 0.22665(7) 0.0195(2) Uani 1 1 d . . . . .
C14 C 0.13043(6) 0.42320(10) 0.23167(7) 0.0203(2) Uani 1 1 d . . . . .
C15 C 0.13587(6) 0.28567(11) 0.24744(7) 0.0244(2) Uani 1 1 d . . . . .
C16 C 0.20348(7) 0.22849(12) 0.29311(8) 0.0302(3) Uani 1 1 d . . . . .
H16 H 0.207129 0.136371 0.30448 0.036 Uiso 1 1 calc R U . . .
C17 C 0.26498(7) 0.30374(13) 0.32192(8) 0.0321(3) Uani 1 1 d . . . . .
H17 H 0.310523 0.263249 0.35287 0.038 Uiso 1 1 calc R U . . .
C18 C 0.26061(6) 0.43870(13) 0.30584(8) 0.0301(3) Uani 1 1 d . . . . .
H18 H 0.302982 0.490499 0.325066 0.036 Uiso 1 1 calc R U . . .
C19 C 0.19407(6) 0.49667(11) 0.26166(7) 0.0246(2) Uani 1 1 d . . . . .
H19 H 0.191331 0.589034 0.25127 0.03 Uiso 1 1 calc R U . . .
N1 N -0.06094(5) 0.47504(9) 0.10727(6) 0.0233(2) Uani 1 1 d . . . . .
N2 N -0.30829(6) 0.62593(10) -0.09190(7) 0.0324(2) Uani 1 1 d . . . . .
N3 N 0.00444(5) 0.41459(9) 0.15336(6) 0.02117(19) Uani 1 1 d . . . . .
O1 O -0.12054(4) 0.28042(8) 0.05804(6) 0.0318(2) Uani 1 1 d . . . . .
O2 O 0.09561(4) 0.69679(8) 0.31188(5) 0.02388(18) Uani 1 1 d . . . . .
O3 O 0.07849(5) 0.20449(8) 0.21997(6) 0.0337(2) Uani 1 1 d . . . . .
H1 H -0.0664(8) 0.5585(16) 0.1199(10) 0.037(4) Uiso 1 1 d . . . . .
H2 H 0.1230(10) 0.768(2) 0.3467(12) 0.062(5) Uiso 1 1 d . . . . .
H3 H 0.0405(11) 0.2535(19) 0.1922(12) 0.058(5) Uiso 1 1 d . . . . .
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 0 '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 0.006 '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
C5 C1 C2 118.61(10) . .
C5 C1 C6 119.47(10) . .
C2 C1 C6 121.82(10) . .
C3 C2 C1 118.46(11) . .
C3 C2 H2A 120.8 . .
C1 C2 H2A 120.8 . .
N2 C3 C2 123.24(12) . .
N2 C3 H3A 118.4 . .
C2 C3 H3A 118.4 . .
N2 C4 C5 123.12(11) . .
N2 C4 H4 118.4 . .
C5 C4 H4 118.4 . .
C4 C5 C1 118.71(11) . .
C4 C5 H5 120.6 . .
C1 C5 H5 120.6 . .
O1 C6 N1 124.84(10) . .
O1 C6 C1 122.67(10) . .
N1 C6 C1 112.39(9) . .
N3 C7 C14 116.90(9) . .
N3 C7 C8 121.86(9) . .
C14 C7 C8 121.03(9) . .
C9 C8 C13 118.81(10) . .
C9 C8 C7 117.69(9) . .
C13 C8 C7 123.48(9) . .
C10 C9 C8 121.63(11) . .
C10 C9 H9 119.2 . .
C8 C9 H9 119.2 . .
C9 C10 C11 118.86(11) . .
C9 C10 H10 120.6 . .
C11 C10 H10 120.6 . .
C12 C11 C10 120.83(11) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C11 C12 C13 120.24(11) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
O2 C13 C12 121.08(10) . .
O2 C13 C8 119.30(9) . .
C12 C13 C8 119.61(10) . .
C19 C14 C15 118.02(10) . .
C19 C14 C7 119.91(9) . .
C15 C14 C7 122.05(10) . .
O3 C15 C16 117.19(10) . .
O3 C15 C14 123.33(10) . .
C16 C15 C14 119.48(10) . .
C17 C16 C15 120.98(11) . .
C17 C16 H16 119.5 . .
C15 C16 H16 119.5 . .
C16 C17 C18 120.26(11) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C19 C18 C17 119.33(11) . .
C19 C18 H18 120.3 . .
C17 C18 H18 120.3 . .
C18 C19 C14 121.92(11) . .
C18 C19 H19 119 . .
C14 C19 H19 119 . .
C6 N1 N3 119.52(9) . .
C6 N1 H1 119.4(10) . .
N3 N1 H1 118.8(10) . .
C4 N2 C3 117.82(11) . .
C7 N3 N1 117.39(9) . .
C13 O2 H2 107.7(11) . .
C15 O3 H3 106.8(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C5 1.3886(15) .
C1 C2 1.3896(16) .
C1 C6 1.5047(15) .
C2 C3 1.3854(17) .
C2 H2A 0.95 .
C3 N2 1.3366(18) .
C3 H3A 0.95 .
C4 N2 1.3347(17) .
C4 C5 1.3840(16) .
C4 H4 0.95 .
C5 H5 0.95 .
C6 O1 1.2130(13) .
C6 N1 1.3628(13) .
C7 N3 1.2948(13) .
C7 C14 1.4699(14) .
C7 C8 1.4986(14) .
C8 C9 1.3959(15) .
C8 C13 1.3980(14) .
C9 C10 1.3831(16) .
C9 H9 0.95 .
C10 C11 1.3862(19) .
C10 H10 0.95 .
C11 C12 1.3807(17) .
C11 H11 0.95 .
C12 C13 1.3980(14) .
C12 H12 0.95 .
C13 O2 1.3577(13) .
C14 C19 1.4022(15) .
C14 C15 1.4151(15) .
C15 O3 1.3506(14) .
C15 C16 1.3972(16) .
C16 C17 1.3785(18) .
C16 H16 0.95 .
C17 C18 1.3905(18) .
C17 H17 0.95 .
C18 C19 1.3808(15) .
C18 H18 0.95 .
C19 H19 0.95 .
N1 N3 1.3779(12) .
N1 H1 0.892(16) .
O2 H2 0.95(2) .
O3 H3 0.88(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.892(16) 2.068(16) 2.8814(12) 151.1(14) 2 yes
O2 H2 N2 0.95(2) 1.73(2) 2.6512(13) 164.5(18) 8_566 yes
O3 H3 N3 0.88(2) 1.80(2) 2.5802(12) 147.8(18) . yes
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
C5 C1 C2 C3 1.17(18) . . . .
C6 C1 C2 C3 177.68(11) . . . .
C1 C2 C3 N2 0.6(2) . . . .
N2 C4 C5 C1 0.74(19) . . . .
C2 C1 C5 C4 -1.80(17) . . . .
C6 C1 C5 C4 -178.38(10) . . . .
C5 C1 C6 O1 37.58(16) . . . .
C2 C1 C6 O1 -138.90(12) . . . .
C5 C1 C6 N1 -146.01(11) . . . .
C2 C1 C6 N1 37.52(15) . . . .
N3 C7 C8 C9 -63.94(14) . . . .
C14 C7 C8 C9 110.79(11) . . . .
N3 C7 C8 C13 114.55(12) . . . .
C14 C7 C8 C13 -70.72(14) . . . .
C13 C8 C9 C10 -0.18(17) . . . .
C7 C8 C9 C10 178.39(11) . . . .
C8 C9 C10 C11 -1.2(2) . . . .
C9 C10 C11 C12 1.4(2) . . . .
C10 C11 C12 C13 -0.14(19) . . . .
C11 C12 C13 O2 179.04(10) . . . .
C11 C12 C13 C8 -1.25(16) . . . .
C9 C8 C13 O2 -178.89(9) . . . .
C7 C8 C13 O2 2.63(15) . . . .
C9 C8 C13 C12 1.40(15) . . . .
C7 C8 C13 C12 -177.08(10) . . . .
N3 C7 C14 C19 176.51(10) . . . .
C8 C7 C14 C19 1.53(15) . . . .
N3 C7 C14 C15 -1.69(15) . . . .
C8 C7 C14 C15 -176.67(10) . . . .
C19 C14 C15 O3 -178.47(10) . . . .
C7 C14 C15 O3 -0.24(17) . . . .
C19 C14 C15 C16 1.10(16) . . . .
C7 C14 C15 C16 179.33(10) . . . .
O3 C15 C16 C17 178.66(11) . . . .
C14 C15 C16 C17 -0.94(18) . . . .
C15 C16 C17 C18 0.01(19) . . . .
C16 C17 C18 C19 0.73(19) . . . .
C17 C18 C19 C14 -0.54(18) . . . .
C15 C14 C19 C18 -0.37(16) . . . .
C7 C14 C19 C18 -178.64(10) . . . .
O1 C6 N1 N3 1.25(17) . . . .
C1 C6 N1 N3 -175.07(9) . . . .
C5 C4 N2 C3 0.97(19) . . . .
C2 C3 N2 C4 -1.6(2) . . . .
C14 C7 N3 N1 -179.52(9) . . . .
C8 C7 N3 N1 -4.59(15) . . . .
C6 N1 N3 C7 168.07(10) . . . .
