#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/88/2228883.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_2228883
loop_
_publ_author_name
'Mao, Fu-Lin'
'Dai, Chun-Hua'
_publ_section_title
;
 (E)-N'-(3-Hydroxybenzylidene)-3-nitrobenzohydrazide
;
_journal_coeditor_code           SJ5070
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o7
_journal_paper_doi               10.1107/S1600536810049482
_journal_volume                  67
_journal_year                    2011
_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
;
(E)-N'-(3-Hydroxybenzylidene)-3-nitrobenzohydrazide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 120.324(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.154(3)
_cell_length_b                   13.295(3)
_cell_length_c                   13.537(2)
_cell_measurement_reflns_used    1285
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.3
_cell_volume                     2509.5(8)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6631
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9743
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0639P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                1588
_reflns_number_total             2738
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5070.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2228883
_cod_database_fobs_code          2228883
loop_
_symmetry_equiv_pos_as_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_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 1.05387(12) 0.55191(13) 0.15027(16) 0.0401(5) Uani d . 1 . .
N N2 0.95666(13) 0.55067(14) 0.10982(17) 0.0422(5) Uani d D 1 . .
N N3 0.59440(14) 0.63671(15) -0.07753(18) 0.0489(5) Uani d . 1 . .
O O1 1.36619(12) 0.85288(13) 0.36202(19) 0.0695(6) Uani d D 1 . .
O O2 0.95061(11) 0.38209(12) 0.09885(16) 0.0594(5) Uani d . 1 . .
O O3 0.50831(13) 0.62855(15) -0.1151(2) 0.0883(8) Uani d . 1 . .
O O4 0.63203(12) 0.71586(13) -0.07821(16) 0.0605(5) Uani d . 1 . .
C C1 1.19663(15) 0.65018(16) 0.22714(18) 0.0371(5) Uani d . 1 . .
C C2 1.23682(17) 0.74283(17) 0.2723(2) 0.0455(6) Uani d . 1 . .
H H2 1.1981 0.7940 0.2736 0.055 Uiso calc R 1 . .
C C3 1.33314(17) 0.76106(16) 0.3155(2) 0.0427(6) Uani d . 1 . .
C C4 1.39012(16) 0.68658(17) 0.3115(2) 0.0458(6) Uani d . 1 . .
H H4 1.4547 0.6986 0.3377 0.055 Uiso calc R 1 . .
C C5 1.35046(16) 0.59342(18) 0.2679(2) 0.0482(6) Uani d . 1 . .
H H5 1.3892 0.5425 0.2662 0.058 Uiso calc R 1 . .
C C6 1.25507(16) 0.57453(18) 0.22723(19) 0.0433(6) Uani d . 1 . .
H H6 1.2299 0.5110 0.1998 0.052 Uiso calc R 1 . .
C C7 1.09381(16) 0.63653(17) 0.1815(2) 0.0435(6) Uani d . 1 . .
H H7 1.0567 0.6922 0.1753 0.052 Uiso calc R 1 . .
C C8 0.91039(16) 0.46268(17) 0.08701(19) 0.0386(5) Uani d . 1 . .
C C9 0.80596(15) 0.46724(16) 0.04857(18) 0.0368(5) Uani d . 1 . .
C C10 0.75046(15) 0.55308(16) 0.00497(18) 0.0385(5) Uani d . 1 . .
H H10 0.7774 0.6130 -0.0008 0.046 Uiso calc R 1 . .
C C11 0.65446(15) 0.54756(16) -0.02961(19) 0.0383(5) Uani d . 1 . .
C C12 0.61190(17) 0.46063(17) -0.0223(2) 0.0458(6) Uani d . 1 . .
H H12 0.5469 0.4590 -0.0461 0.055 Uiso calc R 1 . .
C C13 0.66761(17) 0.37664(18) 0.0209(2) 0.0501(6) Uani d . 1 . .
H H13 0.6403 0.3169 0.0264 0.060 Uiso calc R 1 . .
C C14 0.76350(16) 0.37974(17) 0.0561(2) 0.0444(6) Uani d . 1 . .
H H14 0.8005 0.3220 0.0856 0.053 Uiso calc R 1 . .
H H2A 0.9284(18) 0.6098(12) 0.104(2) 0.080 Uiso d D 1 . .
H H1 1.4208(11) 0.863(2) 0.369(2) 0.080 Uiso d 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 . . 115.61(18) ?
C8 N2 N1 . . 119.61(18) ?
C8 N2 H2A . . 123.3(19) ?
N1 N2 H2A . . 117.0(19) ?
O4 N3 O3 . . 122.8(2) ?
O4 N3 C11 . . 118.86(19) ?
O3 N3 C11 . . 118.3(2) ?
C3 O1 H1 . . 110(2) ?
C6 C1 C2 . . 118.7(2) ?
C6 C1 C7 . . 122.8(2) ?
C2 C1 C7 . . 118.5(2) ?
C3 C2 C1 . . 121.4(2) ?
C3 C2 H2 . . 119.3 ?
C1 C2 H2 . . 119.3 ?
O1 C3 C4 . . 123.7(2) ?
O1 C3 C2 . . 116.8(2) ?
C4 C3 C2 . . 119.5(2) ?
C3 C4 C5 . . 119.2(2) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C6 C5 C4 . . 121.3(2) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C1 . . 119.8(2) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
N1 C7 C1 . . 122.2(2) ?
N1 C7 H7 . . 118.9 ?
C1 C7 H7 . . 118.9 ?
O2 C8 N2 . . 122.6(2) ?
O2 C8 C9 . . 120.9(2) ?
N2 C8 C9 . . 116.47(19) ?
C14 C9 C10 . . 119.1(2) ?
C14 C9 C8 . . 117.1(2) ?
C10 C9 C8 . . 123.7(2) ?
C11 C10 C9 . . 118.4(2) ?
C11 C10 H10 . . 120.8 ?
C9 C10 H10 . . 120.8 ?
C12 C11 C10 . . 122.6(2) ?
C12 C11 N3 . . 118.1(2) ?
C10 C11 N3 . . 119.30(19) ?
C13 C12 C11 . . 118.2(2) ?
C13 C12 H12 . . 120.9 ?
C11 C12 H12 . . 120.9 ?
C12 C13 C14 . . 120.5(2) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C13 C14 C9 . . 121.0(2) ?
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 . 1.259(3) ?
N1 N2 . 1.378(2) ?
N2 C8 . 1.338(3) ?
N2 H2A . 0.892(10) ?
N3 O4 . 1.218(2) ?
N3 O3 . 1.221(2) ?
N3 C11 . 1.460(3) ?
O1 C3 . 1.354(3) ?
O1 H1 . 0.850(10) ?
O2 C8 . 1.221(2) ?
C1 C6 . 1.379(3) ?
C1 C2 . 1.383(3) ?
C1 C7 . 1.462(3) ?
C2 C3 . 1.379(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.372(3) ?
C4 C5 . 1.382(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.372(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.495(3) ?
C9 C14 . 1.380(3) ?
C9 C10 . 1.386(3) ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.374(3) ?
C12 C13 . 1.366(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.372(3) ?
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
O1 H1 N1 4_755 0.850(10) 2.58(3) 2.986(2) 111(2)
O1 H1 O2 4_755 0.850(10) 1.912(11) 2.758(2) 174(3)
N2 H2A O4 7_665 0.892(10) 2.471(11) 3.354(3) 171(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7834926
