#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227413.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_2227413
loop_
_publ_author_name
'Dai, Chun-Hua'
'Mao, Fu-Lin'
_publ_section_title
;
 N'-(3-Hydroxybenzylidene)-4-nitrobenzohydrazide
;
_journal_coeditor_code           FB2226
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3004
_journal_page_last               o3005
_journal_paper_doi               10.1107/S1600536810043564
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H11 N3 O4'
_chemical_formula_moiety         'C14 H11 N3 O4'
_chemical_formula_sum            'C14 H11 N3 O4'
_chemical_formula_weight         285.26
_chemical_name_systematic
;
N'-(3-Hydroxybenzylidene)-4-nitrobenzohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.560(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.987(3)
_cell_length_b                   8.967(3)
_cell_length_c                   15.108(4)
_cell_measurement_reflns_used    1436
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.7
_cell_volume                     1296.9(7)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6579
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.173
_refine_ls_extinction_coef       0.0088(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0444
_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)+(0.0537P)²+0.0632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1787
_reflns_number_total             2768
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2226.cif
_cod_data_source_block           I
_cod_original_cell_volume        1296.8(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227413
_cod_database_fobs_code          2227413
loop_
_symmetry_equiv_pos_as_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_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
N N1 0.00619(14) 0.30350(16) 0.94081(9) 0.0406(4) Uani d . 1 . .
N N2 0.12358(14) 0.36267(16) 1.00310(10) 0.0398(4) Uani d . 1 . .
N N3 0.69398(17) 0.6801(2) 1.24192(14) 0.0589(5) Uani d . 1 . .
O O1 -0.42069(13) 0.13866(16) 0.68671(8) 0.0555(4) Uani d . 1 . .
H H1 -0.493(2) 0.089(2) 0.6608(16) 0.083 Uiso d . 1 . .
O O2 0.16825(12) 0.52109(15) 0.89819(8) 0.0533(4) Uani d . 1 . .
O O3 0.76141(18) 0.7733(2) 1.21577(13) 0.0993(6) Uani d . 1 . .
O O4 0.72752(16) 0.62850(19) 1.31937(12) 0.0842(6) Uani d . 1 . .
C C1 -0.18157(16) 0.12789(18) 0.91821(11) 0.0359(4) Uani d . 1 . .
C C2 -0.24225(16) 0.16628(19) 0.82649(11) 0.0372(4) Uani d . 1 . .
H H2A -0.2025 0.2405 0.7992 0.045 Uiso calc R 1 . .
C C3 -0.36203(17) 0.0939(2) 0.77569(11) 0.0385(4) Uani d . 1 . .
C C4 -0.42103(19) -0.0178(2) 0.81556(13) 0.0452(5) Uani d . 1 . .
H H4 -0.5005 -0.0675 0.7810 0.054 Uiso calc R 1 . .
C C5 -0.3613(2) -0.0546(2) 0.90643(14) 0.0502(5) Uani d . 1 . .
H H5 -0.4015 -0.1290 0.9334 0.060 Uiso calc R 1 . .
C C6 -0.24222(18) 0.0171(2) 0.95848(13) 0.0449(5) Uani d . 1 . .
H H6 -0.2029 -0.0086 1.0201 0.054 Uiso calc R 1 . .
C C7 -0.05675(17) 0.20413(19) 0.97439(12) 0.0393(4) Uani d . 1 . .
H H7 -0.0222 0.1794 1.0365 0.047 Uiso calc R 1 . .
C C8 0.19947(16) 0.4687(2) 0.97659(12) 0.0369(4) Uani d . 1 . .
C C9 0.32783(16) 0.52089(18) 1.04872(11) 0.0341(4) Uani d . 1 . .
C C10 0.39976(17) 0.64059(19) 1.02656(12) 0.0400(4) Uani d . 1 . .
H H10 0.3676 0.6855 0.9689 0.048 Uiso calc R 1 . .
C C11 0.51947(18) 0.6937(2) 1.09002(13) 0.0438(5) Uani d . 1 . .
H H11 0.5681 0.7742 1.0756 0.053 Uiso calc R 1 . .
C C12 0.56488(16) 0.62500(19) 1.17461(12) 0.0410(5) Uani d . 1 . .
C C13 0.49633(17) 0.50675(19) 1.19882(12) 0.0437(5) Uani d . 1 . .
H H13 0.5292 0.4624 1.2566 0.052 Uiso calc R 1 . .
C C14 0.37696(16) 0.45478(19) 1.13512(11) 0.0407(5) Uani d . 1 . .
H H14 0.3289 0.3745 1.1503 0.049 Uiso calc R 1 . .
H H2 0.1392(19) 0.341(2) 1.0640(14) 0.061 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
C7 N1 N2 . . 114.55(14) ?
C8 N2 N1 . . 120.57(14) ?
C8 N2 H2 . . 120.2(12) ?
N1 N2 H2 . . 118.3(12) ?
O3 N3 O4 . . 123.56(18) ?
O3 N3 C12 . . 117.62(19) ?
O4 N3 C12 . . 118.81(18) ?
C3 O1 H1 . . 111.7(16) ?
C2 C1 C6 . . 119.55(15) ?
C2 C1 C7 . . 121.39(16) ?
C6 C1 C7 . . 119.04(15) ?
C3 C2 C1 . . 119.96(17) ?
C3 C2 H2A . . 120.0 ?
C1 C2 H2A . . 120.0 ?
O1 C3 C4 . . 121.66(15) ?
O1 C3 C2 . . 117.95(16) ?
C4 C3 C2 . . 120.37(16) ?
C5 C4 C3 . . 119.48(16) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 120.98(18) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C5 C6 C1 . . 119.64(17) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
N1 C7 C1 . . 122.05(16) ?
N1 C7 H7 . . 119.0 ?
C1 C7 H7 . . 119.0 ?
O2 C8 N2 . . 123.16(15) ?
O2 C8 C9 . . 120.68(16) ?
N2 C8 C9 . . 116.16(15) ?
C10 C9 C14 . . 119.29(15) ?
C10 C9 C8 . . 117.42(15) ?
C14 C9 C8 . . 123.29(16) ?
C9 C10 C11 . . 120.24(16) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C12 C11 C10 . . 118.70(17) ?
C12 C11 H11 . . 120.7 ?
C10 C11 H11 . . 120.7 ?
C13 C12 C11 . . 122.60(15) ?
C13 C12 N3 . . 118.64(17) ?
C11 C12 N3 . . 118.75(17) ?
C12 C13 C14 . . 118.26(16) ?
C12 C13 H13 . . 120.9 ?
C14 C13 H13 . . 120.9 ?
C13 C14 C9 . . 120.91(17) ?
C13 C14 H14 . . 119.5 ?
C9 C14 H14 . . 119.5 ?
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
N1 C7 . 1.276(2) ?
N1 N2 . 1.3830(18) ?
N2 C8 . 1.346(2) ?
N2 H2 . 0.91(2) ?
N3 O3 . 1.208(2) ?
N3 O4 . 1.213(2) ?
N3 C12 . 1.481(2) ?
O1 C3 . 1.365(2) ?
O1 H1 . 0.85(2) ?
O2 C8 . 1.229(2) ?
C1 C2 . 1.388(2) ?
C1 C6 . 1.391(2) ?
C1 C7 . 1.462(2) ?
C2 C3 . 1.385(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.384(2) ?
C4 C5 . 1.372(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.501(2) ?
C9 C10 . 1.385(2) ?
C9 C14 . 1.390(2) ?
C10 C11 . 1.386(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.374(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.367(2) ?
C13 C14 . 1.382(2) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
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
N2 H2 O1 4_666 0.91(2) 2.11(2) 2.931(2) 149.3(16)
O1 H1 O2 2_446 0.85(2) 1.82(2) 2.6573(17) 167(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7891324
