#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/63/2226376.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_2226376
loop_
_publ_author_name
'Liu, Shi-Yong'
'You, Zhonglu'
_publ_section_title
;
 (E)-N'-(4-Hydroxybenzylidene)-2-nitrobenzohydrazide
;
_journal_coeditor_code           CI5099
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1652
_journal_paper_doi               10.1107/S1600536810022075
_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
;
(E)-N'-(4-Hydroxybenzylidene)-2-nitrobenzohydrazide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.720(2)
_cell_length_b                   11.398(3)
_cell_length_c                   15.072(5)
_cell_measurement_reflns_used    633
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     1326.2(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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0845
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7745
_diffrn_reflns_theta_full        26.60
_diffrn_reflns_theta_max         26.60
_diffrn_reflns_theta_min         2.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         1602
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_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)+(0.0542P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                961
_reflns_number_total             1602
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5099.cif
_cod_data_source_block           I
_cod_original_cell_volume        1326.3(7)
_cod_database_code               2226376
_cod_database_fobs_code          2226376
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
N N1 0.1071(5) 0.7318(3) 1.03691(19) 0.0490(10) Uani d . 1 . .
N N2 0.1251(5) 0.7909(3) 0.9568(2) 0.0486(9) Uani d D 1 . .
N N3 0.2475(6) 1.1354(4) 0.9364(3) 0.0729(13) Uani d . 1 . .
O O1 0.1478(4) 0.3516(2) 1.34410(16) 0.0478(8) Uani d . 1 . .
H H1 0.0826 0.3784 1.3820 0.072 Uiso calc R 1 . .
O O2 0.0109(4) 0.9556(2) 1.01482(16) 0.0498(8) Uani d . 1 . .
O O3 0.3197(5) 1.0807(4) 0.9939(2) 0.0846(12) Uani d . 1 . .
O O4 0.2255(9) 1.2411(4) 0.9389(3) 0.151(2) Uani d . 1 . .
C C1 0.1311(5) 0.5519(3) 1.1159(2) 0.0386(9) Uani d . 1 . .
C C2 0.0734(5) 0.5986(3) 1.1956(2) 0.0415(10) Uani d . 1 . .
H H2 0.0306 0.6749 1.1971 0.050 Uiso calc R 1 . .
C C3 0.0787(5) 0.5334(3) 1.2728(3) 0.0411(10) Uani d . 1 . .
H H3 0.0418 0.5657 1.3262 0.049 Uiso calc R 1 . .
C C4 0.1396(5) 0.4197(3) 1.2695(2) 0.0362(9) Uani d . 1 . .
C C5 0.1956(5) 0.3714(3) 1.1908(3) 0.0428(10) Uani d . 1 . .
H H5 0.2367 0.2948 1.1892 0.051 Uiso calc R 1 . .
C C6 0.1902(5) 0.4375(3) 1.1148(2) 0.0428(10) Uani d . 1 . .
H H6 0.2271 0.4047 1.0616 0.051 Uiso calc R 1 . .
C C7 0.1348(6) 0.6220(4) 1.0351(2) 0.0452(10) Uani d . 1 . .
H H7 0.1579 0.5856 0.9812 0.054 Uiso calc R 1 . .
C C8 0.0819(5) 0.9035(3) 0.9539(2) 0.0406(10) Uani d . 1 . .
C C9 0.1145(5) 0.9615(3) 0.8660(2) 0.0385(9) Uani d . 1 . .
C C10 0.1817(6) 1.0730(4) 0.8584(3) 0.0470(11) Uani d . 1 . .
C C11 0.1996(6) 1.1296(4) 0.7788(3) 0.0570(12) Uani d . 1 . .
H H11 0.2446 1.2052 0.7762 0.068 Uiso calc R 1 . .
C C12 0.1495(7) 1.0721(5) 0.7024(3) 0.0649(14) Uani d . 1 . .
H H12 0.1618 1.1088 0.6477 0.078 Uiso calc R 1 . .
C C13 0.0821(6) 0.9617(4) 0.7068(3) 0.0609(13) Uani d . 1 . .
H H13 0.0495 0.9228 0.6552 0.073 Uiso calc R 1 . .
C C14 0.0624(5) 0.9078(4) 0.7889(2) 0.0468(11) Uani d . 1 . .
H H14 0.0127 0.8336 0.7917 0.056 Uiso calc R 1 . .
H H2A 0.189(5) 0.755(4) 0.915(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 . . 116.2(3) ?
C8 N2 N1 . . 118.2(3) ?
C8 N2 H2A . . 123(3) ?
N1 N2 H2A . . 117(3) ?
O3 N3 O4 . . 123.7(5) ?
O3 N3 C10 . . 119.1(4) ?
O4 N3 C10 . . 117.2(5) ?
C4 O1 H1 . . 109.5 ?
C6 C1 C2 . . 118.6(3) ?
C6 C1 C7 . . 120.1(3) ?
C2 C1 C7 . . 121.3(3) ?
C3 C2 C1 . . 120.9(3) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C4 C3 C2 . . 119.0(3) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
O1 C4 C5 . . 117.8(3) ?
O1 C4 C3 . . 121.3(3) ?
C5 C4 C3 . . 120.9(3) ?
C6 C5 C4 . . 119.4(3) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 121.2(4) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
N1 C7 C1 . . 121.3(3) ?
N1 C7 H7 . . 119.3 ?
C1 C7 H7 . . 119.3 ?
O2 C8 N2 . . 123.9(3) ?
O2 C8 C9 . . 121.5(3) ?
N2 C8 C9 . . 114.4(3) ?
C14 C9 C10 . . 116.8(4) ?
C14 C9 C8 . . 120.0(4) ?
C10 C9 C8 . . 123.0(3) ?
C11 C10 C9 . . 123.2(4) ?
C11 C10 N3 . . 116.0(4) ?
C9 C10 N3 . . 120.7(4) ?
C10 C11 C12 . . 118.6(4) ?
C10 C11 H11 . . 120.7 ?
C12 C11 H11 . . 120.7 ?
C13 C12 C11 . . 120.4(4) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 119.5(4) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C9 C14 C13 . . 121.6(4) ?
C9 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
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 . 1.270(4) ?
N1 N2 . 1.389(4) ?
N2 C8 . 1.327(5) ?
N2 H2A . 0.900(10) ?
N3 O3 . 1.204(5) ?
N3 O4 . 1.217(5) ?
N3 C10 . 1.466(6) ?
O1 C4 . 1.368(4) ?
O1 H1 . 0.82 ?
O2 C8 . 1.224(4) ?
C1 C6 . 1.381(5) ?
C1 C2 . 1.388(5) ?
C1 C7 . 1.457(5) ?
C2 C3 . 1.381(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.380(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.377(5) ?
C5 C6 . 1.372(5) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 H7 . 0.93 ?
C8 C9 . 1.501(5) ?
C9 C14 . 1.374(5) ?
C9 C10 . 1.377(5) ?
C10 C11 . 1.369(5) ?
C11 C12 . 1.379(6) ?
C11 H11 . 0.93 ?
C12 C13 . 1.363(7) ?
C12 H12 . 0.93 ?
C13 C14 . 1.390(5) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
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 O2 3_547 0.82 1.93 2.725(3) 164
N2 H2A O1 2_564 0.900(10) 2.05(2) 2.932(4) 166(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12668606
