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#$Date: 2022-06-27 11:25:53 +0300 (Mon, 27 Jun 2022) $
#$Revision: 276275 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105523.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_8105523
loop_
_publ_author_name
'Wei, Ping'
'Li, Qing-Lin'
'Ma, Jin-Xia'
'Fu, Tao'
'Zhao, Ji-Xing'
'Zhao, Li'
_publ_section_title
;
 Crystal structure of
 1-{4-[(2-hydroxy-5-nitrobenzylidene)amino]phenyl}ethanone O-methyl oxime,
 C16H15N3O4
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              9
_journal_page_last               10
_journal_paper_doi               10.1515/ncrs-2017-0382
_journal_volume                  234
_journal_year                    2018
_chemical_formula_moiety         'C16 H15 N3 O4'
_chemical_formula_sum            'C16 H15 N3 O4'
_chemical_formula_weight         313.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.113(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4730(5)
_cell_length_b                   8.1564(6)
_cell_length_c                   27.511(2)
_cell_measurement_reflns_used    2968
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.60
_cell_volume                     1452.48(19)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10517
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         2.605
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0623
_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)+(0.0402P)²+1.5999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1360
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1994
_reflns_number_total             2761
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0382_suppl.cif
_cod_data_source_block           2
_cod_original_cell_volume        1452.47(19)
_cod_database_code               8105523
_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_max   0.981
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C9(H9), C5(H5), C10(H10), C12(H12), C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
loop_
_space_group_symop_operation_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_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
O4 O -0.3329(3) 0.2071(2) 0.74924(6) 0.0245(4) Uani 1 1 d . . . . .
O1 O 0.3377(3) 0.0958(2) 0.43386(7) 0.0270(5) Uani 1 1 d . . . . .
H1 H 0.301816 0.114338 0.462674 0.041 Uiso 1 1 calc GR . . . .
O3 O 1.1878(3) 0.4547(2) 0.42946(7) 0.0312(5) Uani 1 1 d . . . . .
O2 O 1.1718(3) 0.3664(3) 0.35528(7) 0.0371(5) Uani 1 1 d . . . . .
N2 N 0.3586(3) 0.2081(3) 0.52036(8) 0.0214(5) Uani 1 1 d . . . . .
N1 N 1.1006(3) 0.3794(3) 0.39660(8) 0.0267(5) Uani 1 1 d . . . . .
N3 N -0.2372(3) 0.1849(3) 0.70339(7) 0.0212(5) Uani 1 1 d . . . . .
C8 C 0.2620(4) 0.2284(3) 0.56615(9) 0.0201(6) Uani 1 1 d . . . . .
C11 C 0.0405(4) 0.2599(3) 0.65329(9) 0.0192(6) Uani 1 1 d . . . . .
C7 C 0.5400(4) 0.2657(3) 0.51103(9) 0.0228(6) Uani 1 1 d . . . . .
H7 H 0.615311 0.320955 0.535772 0.027 Uiso 1 1 calc R . . . .
C1 C 0.5217(4) 0.1635(3) 0.42570(9) 0.0216(6) Uani 1 1 d . . . . .
C14 C -0.0775(4) 0.2767(3) 0.69943(9) 0.0201(6) Uani 1 1 d . . . . .
C6 C 0.6297(4) 0.2469(3) 0.46310(9) 0.0207(6) Uani 1 1 d . . . . .
C13 C 0.3455(4) 0.3148(3) 0.60506(10) 0.0247(6) Uani 1 1 d . . . . .
H13 H 0.478052 0.363809 0.602306 0.030 Uiso 1 1 calc R . . . .
C9 C 0.0675(4) 0.1574(3) 0.57121(9) 0.0222(6) Uani 1 1 d . . . . .
H9 H 0.009638 0.097859 0.544810 0.027 Uiso 1 1 calc R . . . .
C5 C 0.8218(4) 0.3150(3) 0.45297(10) 0.0234(6) Uani 1 1 d . . . . .
H5 H 0.896612 0.370242 0.477793 0.028 Uiso 1 1 calc R . . . .
C4 C 0.9032(4) 0.3025(3) 0.40707(10) 0.0233(6) Uani 1 1 d . . . . .
C10 C -0.0428(4) 0.1720(3) 0.61390(10) 0.0230(6) Uani 1 1 d . . . . .
H10 H -0.175170 0.122617 0.616664 0.028 Uiso 1 1 calc R . . . .
C15 C -0.0023(4) 0.3938(4) 0.73773(9) 0.0253(6) Uani 1 1 d . . . . .
H15A H -0.118197 0.426558 0.758429 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.056782 0.491037 0.722132 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.103684 0.340065 0.757630 0.038 Uiso 1 1 calc GR . . . .
C12 C 0.2352(4) 0.3292(3) 0.64766(10) 0.0245(6) Uani 1 1 d . . . . .
H12 H 0.294147 0.388250 0.674011 0.029 Uiso 1 1 calc R . . . .
C3 C 0.7966(4) 0.2219(3) 0.36985(10) 0.0263(6) Uani 1 1 d . . . . .
H3 H 0.854936 0.214907 0.338257 0.032 Uiso 1 1 calc R . . . .
C16 C -0.5094(4) 0.1022(4) 0.75079(10) 0.0281(7) Uani 1 1 d . . . . .
H16A H -0.605984 0.133166 0.724903 0.042 Uiso 1 1 calc GR . . . .
H16B H -0.577560 0.113213 0.782398 0.042 Uiso 1 1 calc GR . . . .
H16C H -0.465680 -0.011745 0.746140 0.042 Uiso 1 1 calc GR . . . .
C2 C 0.6078(4) 0.1533(4) 0.37912(10) 0.0269(7) Uani 1 1 d . . . . .
H2 H 0.535009 0.098460 0.353891 0.032 Uiso 1 1 calc 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N3 O4 C16 107.52(19) . .
C1 O1 H1 109.5 . .
C7 N2 C8 122.5(2) . .
O3 N1 O2 123.3(2) . .
O3 N1 C4 118.2(2) . .
O2 N1 C4 118.5(2) . .
C14 N3 O4 110.8(2) . .
C13 C8 N2 124.9(2) . .
C13 C8 C9 118.9(2) . .
C9 C8 N2 116.2(2) . .
C10 C11 C14 120.5(2) . .
C12 C11 C14 121.6(2) . .
C12 C11 C10 117.9(2) . .
N2 C7 H7 119.7 . .
N2 C7 C6 120.5(2) . .
C6 C7 H7 119.7 . .
O1 C1 C6 121.1(2) . .
O1 C1 C2 119.2(2) . .
C2 C1 C6 119.7(2) . .
N3 C14 C11 115.7(2) . .
N3 C14 C15 124.9(2) . .
C11 C14 C15 119.4(2) . .
C1 C6 C7 120.9(2) . .
C5 C6 C7 120.0(2) . .
C5 C6 C1 119.1(2) . .
C8 C13 H13 120.1 . .
C12 C13 C8 119.8(3) . .
C12 C13 H13 120.1 . .
C8 C9 H9 119.4 . .
C10 C9 C8 121.2(2) . .
C10 C9 H9 119.4 . .
C6 C5 H5 120.0 . .
C4 C5 C6 120.0(3) . .
C4 C5 H5 120.0 . .
C5 C4 N1 119.3(2) . .
C5 C4 C3 121.3(3) . .
C3 C4 N1 119.4(2) . .
C11 C10 H10 120.0 . .
C9 C10 C11 120.1(2) . .
C9 C10 H10 120.0 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C11 C12 H12 118.9 . .
C13 C12 C11 122.1(3) . .
C13 C12 H12 118.9 . .
C4 C3 H3 120.2 . .
C2 C3 C4 119.7(2) . .
C2 C3 H3 120.2 . .
O4 C16 H16A 109.5 . .
O4 C16 H16B 109.5 . .
O4 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C1 C2 H2 119.9 . .
C3 C2 C1 120.2(3) . .
C3 C2 H2 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 N3 1.418(3) .
O4 C16 1.428(3) .
O1 H1 0.8400 .
O1 C1 1.332(3) .
O3 N1 1.229(3) .
O2 N1 1.232(3) .
N2 C8 1.417(3) .
N2 C7 1.291(3) .
N1 C4 1.453(3) .
N3 C14 1.281(3) .
C8 C13 1.390(4) .
C8 C9 1.393(4) .
C11 C14 1.489(4) .
C11 C10 1.406(4) .
C11 C12 1.390(4) .
C7 H7 0.9500 .
C7 C6 1.450(4) .
C1 C6 1.417(4) .
C1 C2 1.401(4) .
C14 C15 1.502(4) .
C6 C5 1.391(4) .
C13 H13 0.9500 .
C13 C12 1.378(4) .
C9 H9 0.9500 .
C9 C10 1.381(4) .
C5 H5 0.9500 .
C5 C4 1.373(4) .
C4 C3 1.398(4) .
C10 H10 0.9500 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C12 H12 0.9500 .
C3 H3 0.9500 .
C3 C2 1.369(4) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C2 H2 0.9500 .
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
O4 N3 C14 C11 178.0(2) . . . .
O4 N3 C14 C15 -0.6(3) . . . .
O1 C1 C6 C7 -2.0(4) . . . .
O1 C1 C6 C5 179.7(2) . . . .
O1 C1 C2 C3 179.9(3) . . . .
O3 N1 C4 C5 -0.5(4) . . . .
O3 N1 C4 C3 177.3(2) . . . .
O2 N1 C4 C5 179.7(3) . . . .
O2 N1 C4 C3 -2.4(4) . . . .
N2 C8 C13 C12 178.7(3) . . . .
N2 C8 C9 C10 -178.7(3) . . . .
N2 C7 C6 C1 -0.7(4) . . . .
N2 C7 C6 C5 177.5(3) . . . .
N1 C4 C3 C2 -178.2(2) . . . .
C8 N2 C7 C6 -177.9(2) . . . .
C8 C13 C12 C11 -0.2(4) . . . .
C8 C9 C10 C11 0.1(4) . . . .
C7 N2 C8 C13 2.1(4) . . . .
C7 N2 C8 C9 -179.0(3) . . . .
C7 C6 C5 C4 -177.5(3) . . . .
C1 C6 C5 C4 0.7(4) . . . .
C14 C11 C10 C9 179.8(2) . . . .
C14 C11 C12 C13 -179.8(3) . . . .
C6 C1 C2 C3 0.7(4) . . . .
C6 C5 C4 N1 177.8(2) . . . .
C6 C5 C4 C3 0.0(4) . . . .
C13 C8 C9 C10 0.2(4) . . . .
C9 C8 C13 C12 -0.1(4) . . . .
C5 C4 C3 C2 -0.3(4) . . . .
C4 C3 C2 C1 0.0(4) . . . .
C10 C11 C14 N3 11.5(4) . . . .
C10 C11 C14 C15 -169.8(2) . . . .
C10 C11 C12 C13 0.5(4) . . . .
C12 C11 C14 N3 -168.3(2) . . . .
C12 C11 C14 C15 10.4(4) . . . .
C12 C11 C10 C9 -0.4(4) . . . .
C16 O4 N3 C14 179.6(2) . . . .
C2 C1 C6 C7 177.2(3) . . . .
C2 C1 C6 C5 -1.0(4) . . . .
