#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/91/2229117.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_2229117
loop_
_publ_author_name
'Mohd Lair, Nooraziah'
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
_publ_section_title
;
 (E)-N'-(2,4-Dihydroxybenzylidene)-4-nitrobenzohydrazide
;
_journal_coeditor_code           IS2667
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o459
_journal_paper_doi               10.1107/S1600536811002224
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H11 N3 O5'
_chemical_formula_moiety         'C14 H11 N3 O5'
_chemical_formula_sum            'C14 H11 N3 O5'
_chemical_formula_weight         301.26
_chemical_name_systematic
;
(E)-N'-(2,4-Dihydroxybenzylidene)-4-nitrobenzohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.7320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.02480(10)
_cell_length_b                   12.5674(2)
_cell_length_c                   12.8770(2)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      3.19
_cell_volume                     1289.70(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10373
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0584P)²+0.2741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2004
_reflns_number_total             2398
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2667.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229117
_cod_database_fobs_code          2229117
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O O1 0.01817(13) 0.64009(9) 1.21087(8) 0.0250(3) Uani d D 1 . .
H H1 0.073(2) 0.5985(14) 1.1740(14) 0.038 Uiso d D 1 . .
O O2 -0.25926(12) 0.97321(8) 1.19160(8) 0.0200(2) Uani d D 1 . .
H H2A -0.271(2) 0.9547(14) 1.2529(12) 0.030 Uiso d D 1 . .
O O3 0.31162(13) 0.40161(8) 1.11922(8) 0.0232(3) Uani d . 1 . .
O O4 0.70514(13) 0.04460(8) 0.83143(8) 0.0287(3) Uani d . 1 . .
O O5 0.69197(12) 0.15345(9) 0.70111(8) 0.0248(3) Uani d . 1 . .
N N1 0.15626(13) 0.57805(9) 1.04095(9) 0.0180(3) Uani d . 1 . .
N N2 0.23932(14) 0.50897(9) 0.98041(9) 0.0173(3) Uani d D 1 . .
H H2B 0.2412(19) 0.5289(12) 0.9163(11) 0.021 Uiso d D 1 . .
N N3 0.66607(14) 0.13011(10) 0.79089(9) 0.0193(3) Uani d . 1 . .
C C1 -0.02829(16) 0.72791(11) 1.15383(11) 0.0170(3) Uani d . 1 . .
C C2 -0.11597(16) 0.80504(11) 1.20227(11) 0.0171(3) Uani d . 1 . .
H H2 -0.1393 0.7950 1.2722 0.021 Uiso calc R 1 . .
C C3 -0.16953(16) 0.89687(11) 1.14835(11) 0.0168(3) Uani d . 1 . .
C C4 -0.13465(16) 0.91253(11) 1.04548(11) 0.0182(3) Uani d . 1 . .
H H4 -0.1708 0.9756 1.0088 0.022 Uiso calc R 1 . .
C C5 -0.04773(16) 0.83605(11) 0.99795(11) 0.0178(3) Uani d . 1 . .
H H5 -0.0243 0.8472 0.9282 0.021 Uiso calc R 1 . .
C C6 0.00759(16) 0.74153(11) 1.04988(11) 0.0165(3) Uani d . 1 . .
C C7 0.09681(16) 0.66335(11) 0.99533(11) 0.0178(3) Uani d . 1 . .
H H7 0.1119 0.6752 0.9242 0.021 Uiso calc R 1 . .
C C8 0.31525(16) 0.42271(11) 1.02595(11) 0.0162(3) Uani d . 1 . .
C C9 0.40734(15) 0.35067(11) 0.95936(10) 0.0156(3) Uani d . 1 . .
C C10 0.44714(16) 0.37683(11) 0.85999(11) 0.0171(3) Uani d . 1 . .
H H10 0.4134 0.4436 0.8299 0.020 Uiso calc R 1 . .
C C11 0.53565(16) 0.30596(11) 0.80500(11) 0.0178(3) Uani d . 1 . .
H H11 0.5651 0.3237 0.7378 0.021 Uiso calc R 1 . .
C C12 0.58004(16) 0.20868(11) 0.85038(11) 0.0171(3) Uani d . 1 . .
C C13 0.54399(16) 0.18076(11) 0.94917(11) 0.0183(3) Uani d . 1 . .
H H13 0.5776 0.1138 0.9788 0.022 Uiso calc R 1 . .
C C14 0.45772(16) 0.25303(11) 1.00359(11) 0.0174(3) Uani d . 1 . .
H H14 0.4325 0.2359 1.0719 0.021 Uiso calc R 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
C1 O1 H1 . . 108.8(13) ?
C3 O2 H2A . . 108.2(12) ?
C7 N1 N2 . . 116.19(12) ?
C8 N2 N1 . . 118.83(12) ?
C8 N2 H2B . . 126.4(11) ?
N1 N2 H2B . . 114.7(11) ?
O4 N3 O5 . . 123.19(12) ?
O4 N3 C12 . . 118.79(12) ?
O5 N3 C12 . . 118.00(12) ?
O1 C1 C2 . . 116.57(12) ?
O1 C1 C6 . . 122.64(12) ?
C2 C1 C6 . . 120.78(13) ?
C1 C2 C3 . . 119.94(13) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
O2 C3 C2 . . 122.02(12) ?
O2 C3 C4 . . 117.61(12) ?
C2 C3 C4 . . 120.36(12) ?
C5 C4 C3 . . 119.47(13) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 121.79(13) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C6 C1 . . 117.65(12) ?
C5 C6 C7 . . 119.27(13) ?
C1 C6 C7 . . 123.09(13) ?
N1 C7 C6 . . 121.51(13) ?
N1 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
O3 C8 N2 . . 122.48(12) ?
O3 C8 C9 . . 119.76(13) ?
N2 C8 C9 . . 117.77(12) ?
C14 C9 C10 . . 119.77(12) ?
C14 C9 C8 . . 115.90(12) ?
C10 C9 C8 . . 124.31(13) ?
C11 C10 C9 . . 120.27(13) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 118.33(13) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
C13 C12 C11 . . 122.80(13) ?
C13 C12 N3 . . 118.07(13) ?
C11 C12 N3 . . 119.12(12) ?
C14 C13 C12 . . 118.11(13) ?
C14 C13 H13 . . 120.9 ?
C12 C13 H13 . . 120.9 ?
C13 C14 C9 . . 120.69(13) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
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
O1 C1 . 1.3537(17) ?
O1 H1 . 0.860(15) ?
O2 C3 . 1.3576(16) ?
O2 H2A . 0.839(14) ?
O3 C8 . 1.2336(16) ?
O4 N3 . 1.2196(16) ?
O5 N3 . 1.2337(15) ?
N1 C7 . 1.2868(19) ?
N1 N2 . 1.3884(16) ?
N2 C8 . 1.3441(19) ?
N2 H2B . 0.865(13) ?
N3 C12 . 1.4705(17) ?
C1 C2 . 1.3880(19) ?
C1 C6 . 1.4121(19) ?
C2 C3 . 1.389(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3996(19) ?
C4 C5 . 1.3729(19) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.409(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4454(19) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.4999(18) ?
C9 C14 . 1.3927(19) ?
C9 C10 . 1.3939(19) ?
C10 C11 . 1.3847(19) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.384(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.3825(19) ?
C13 C14 . 1.3817(19) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
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 . 0.860(15) 1.929(16) 2.6818(15) 145.5(17)
O2 H2A O3 2_557 0.839(14) 1.841(15) 2.6759(14) 173.3(18)
N2 H2B O5 2_656 0.865(13) 2.283(14) 3.0606(16) 149.6(14)
C2 H2 O3 2_557 0.95 2.47 3.1730(17) 131
C4 H4 O4 1_465 0.95 2.54 3.3428(17) 143
C7 H7 O5 2_656 0.95 2.40 3.2082(17) 143
C10 H10 O4 2_656 0.95 2.52 3.3627(18) 147
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12230753
