#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/92/2229244.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_2229244
loop_
_publ_author_name
'Zhang, Zhen'
_publ_section_title
;
 2-Hydroxy-N'-(4-hydroxy-3-nitrobenzylidene)benzohydrazide
;
_journal_coeditor_code           SU2244
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o301
_journal_paper_doi               10.1107/S1600536811000201
_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
;
2-Hydroxy-N'-(4-hydroxy-3-nitrobenzylidene)benzohydrazide
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 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                 131.426(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.769(2)
_cell_length_b                   13.089(2)
_cell_length_c                   19.999(3)
_cell_measurement_reflns_used    2499
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     2702.5(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2008'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20705
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5704
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0741
_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)+(0.0590P)²+0.7268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1653
_reflns_number_gt                3336
_reflns_number_total             5704
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2244.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               2229244
_cod_database_fobs_code          2229244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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 0.2000(3) 0.18864(15) 0.83343(17) 0.0670(7) Uani d . 1 . .
H H1A 0.1778 0.1291 0.8178 0.100 Uiso calc R 1 . .
O O2 0.1875(2) 0.50089(14) 0.86317(14) 0.0588(6) Uani d . 1 . .
O O3 0.4530(4) 0.29706(19) 0.5827(2) 0.1199(13) Uani d . 1 . .
O O4 0.4754(2) 0.42998(17) 0.53343(16) 0.0676(7) Uani d . 1 . .
O O5 0.4360(2) 0.61199(15) 0.56619(16) 0.0591(6) Uani d . 1 . .
H H5 0.4648 0.5741 0.5502 0.089 Uiso calc R 1 . .
O O6 0.2115(2) 0.69519(14) 0.82854(13) 0.0543(6) Uani d . 1 . .
H H6 0.2037 0.6340 0.8329 0.082 Uiso calc R 1 . .
O O7 0.1398(2) 1.00436(14) 0.76080(14) 0.0621(7) Uani d . 1 . .
O O8 0.7151(3) 0.85882(19) 1.33786(16) 0.0998(10) Uani d . 1 . .
O O9 0.8001(3) 0.99999(19) 1.40763(16) 0.0896(9) Uani d . 1 . .
O O10 0.7080(2) 1.17289(16) 1.32351(15) 0.0645(6) Uani d . 1 . .
H H10 0.7641 1.1385 1.3674 0.097 Uiso calc R 1 . .
N N1 0.2146(3) 0.37642(17) 0.79853(17) 0.0477(6) Uani d D 1 . .
N N2 0.2490(2) 0.44197(17) 0.76341(15) 0.0450(6) Uani d . 1 . .
N N3 0.4419(3) 0.3884(2) 0.56981(18) 0.0582(7) Uani d . 1 . .
N N4 0.2472(3) 0.89030(17) 0.87275(16) 0.0480(6) Uani d D 1 . .
N N5 0.3115(2) 0.96498(17) 0.93740(17) 0.0465(6) Uani d . 1 . .
N N6 0.7213(3) 0.9512(2) 1.33793(19) 0.0682(8) Uani d . 1 . .
C C1 0.1415(3) 0.3304(2) 0.87495(17) 0.0387(7) Uani d . 1 . .
C C2 0.1469(3) 0.2249(2) 0.86681(19) 0.0457(7) Uani d . 1 . .
C C3 0.1009(3) 0.1584(2) 0.8941(2) 0.0602(9) Uani d . 1 . .
H H3 0.1042 0.0883 0.8881 0.072 Uiso calc R 1 . .
C C4 0.0508(3) 0.1945(3) 0.9297(2) 0.0618(9) Uani d . 1 . .
H H4A 0.0202 0.1488 0.9477 0.074 Uiso calc R 1 . .
C C5 0.0451(3) 0.2982(3) 0.9393(2) 0.0609(9) Uani d . 1 . .
H H5A 0.0113 0.3228 0.9639 0.073 Uiso calc R 1 . .
C C6 0.0900(3) 0.3642(2) 0.91194(19) 0.0509(8) Uani d . 1 . .
H H6A 0.0860 0.4341 0.9183 0.061 Uiso calc R 1 . .
C C7 0.1842(3) 0.4105(2) 0.84622(17) 0.0398(7) Uani d . 1 . .
C C8 0.2731(3) 0.3978(2) 0.7192(2) 0.0498(8) Uani d . 1 . .
H H8 0.2666 0.3270 0.7141 0.060 Uiso calc R 1 . .
C C9 0.3104(3) 0.4536(2) 0.67645(18) 0.0418(7) Uani d . 1 . .
C C10 0.3520(3) 0.3994(2) 0.64042(19) 0.0468(8) Uani d . 1 . .
H H10A 0.3514 0.3284 0.6412 0.056 Uiso calc R 1 . .
C C11 0.3948(3) 0.4498(2) 0.60285(18) 0.0432(7) Uani d . 1 . .
C C12 0.3946(3) 0.5558(2) 0.59936(18) 0.0425(7) Uani d . 1 . .
C C13 0.3491(3) 0.6095(2) 0.6339(2) 0.0488(8) Uani d . 1 . .
H H13 0.3462 0.6805 0.6311 0.059 Uiso calc R 1 . .
C C14 0.3088(3) 0.5604(2) 0.67171(19) 0.0469(8) Uani d . 1 . .
H H14 0.2798 0.5984 0.6948 0.056 Uiso calc R 1 . .
C C15 0.0970(3) 0.8290(2) 0.72103(18) 0.0370(7) Uani d . 1 . .
C C16 0.1181(3) 0.7249(2) 0.74221(19) 0.0391(7) Uani d . 1 . .
C C17 0.0450(3) 0.6528(2) 0.6754(2) 0.0500(8) Uani d . 1 . .
H H17 0.0587 0.5837 0.6899 0.060 Uiso calc R 1 . .
C C18 -0.0476(3) 0.6822(2) 0.5879(2) 0.0571(9) Uani d . 1 . .
H H18 -0.0967 0.6329 0.5436 0.069 Uiso calc R 1 . .
C C19 -0.0682(3) 0.7839(3) 0.5651(2) 0.0579(9) Uani d . 1 . .
H H19 -0.1298 0.8036 0.5057 0.070 Uiso calc R 1 . .
C C20 0.0033(3) 0.8557(2) 0.6311(2) 0.0470(8) Uani d . 1 . .
H H20 -0.0110 0.9245 0.6155 0.056 Uiso calc R 1 . .
C C21 0.1630(3) 0.9152(2) 0.7860(2) 0.0426(7) Uani d . 1 . .
C C22 0.3914(3) 0.9314(2) 1.0165(2) 0.0625(10) Uani d . 1 . .
H H22 0.3997 0.8609 1.0246 0.075 Uiso calc R 1 . .
C C23 0.4704(3) 0.9952(2) 1.0952(2) 0.0507(8) Uani d . 1 . .
C C24 0.5549(3) 0.9492(2) 1.1772(2) 0.0553(9) Uani d . 1 . .
H H24 0.5581 0.8782 1.1807 0.066 Uiso calc R 1 . .
C C25 0.6354(3) 1.0058(2) 1.2550(2) 0.0477(8) Uani d . 1 . .
C C26 0.6330(3) 1.1123(2) 1.2519(2) 0.0474(8) Uani d . 1 . .
C C27 0.5487(3) 1.1584(2) 1.1691(2) 0.0546(9) Uani d . 1 . .
H H27 0.5465 1.2294 1.1655 0.066 Uiso calc R 1 . .
C C28 0.4687(3) 1.1026(2) 1.0926(2) 0.0535(8) Uani d . 1 . .
H H28 0.4123 1.1360 1.0379 0.064 Uiso calc R 1 . .
H H4 0.270(3) 0.8247(11) 0.891(2) 0.080 Uiso d D 1 . .
H H1 0.212(3) 0.3085(9) 0.791(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
C2 O1 H1A . . 109.5 ?
C12 O5 H5 . . 109.5 ?
C16 O6 H6 . . 109.5 ?
C26 O10 H10 . . 109.5 ?
C7 N1 N2 . . 121.9(2) ?
C7 N1 H1 . . 117(2) ?
N2 N1 H1 . . 121(2) ?
C8 N2 N1 . . 114.1(2) ?
O3 N3 O4 . . 121.6(3) ?
O3 N3 C11 . . 119.1(3) ?
O4 N3 C11 . . 119.2(3) ?
C21 N4 N5 . . 120.7(2) ?
C21 N4 H4 . . 121(2) ?
N5 N4 H4 . . 118(2) ?
C22 N5 N4 . . 114.5(2) ?
O8 N6 O9 . . 121.7(3) ?
O8 N6 C25 . . 119.4(3) ?
O9 N6 C25 . . 118.9(3) ?
C6 C1 C2 . . 117.4(3) ?
C6 C1 C7 . . 116.8(2) ?
C2 C1 C7 . . 125.8(3) ?
O1 C2 C3 . . 120.6(3) ?
O1 C2 C1 . . 119.3(3) ?
C3 C2 C1 . . 120.1(3) ?
C4 C3 C2 . . 120.7(3) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4A . . 119.7 ?
C5 C4 H4A . . 119.7 ?
C6 C5 C4 . . 118.8(3) ?
C6 C5 H5A . . 120.6 ?
C4 C5 H5A . . 120.6 ?
C5 C6 C1 . . 122.3(3) ?
C5 C6 H6A . . 118.8 ?
C1 C6 H6A . . 118.8 ?
O2 C7 N1 . . 123.0(3) ?
O2 C7 C1 . . 121.7(3) ?
N1 C7 C1 . . 115.3(2) ?
N2 C8 C9 . . 122.5(3) ?
N2 C8 H8 . . 118.8 ?
C9 C8 H8 . . 118.8 ?
C10 C9 C14 . . 118.2(3) ?
C10 C9 C8 . . 118.7(3) ?
C14 C9 C8 . . 123.1(3) ?
C9 C10 C11 . . 120.7(3) ?
C9 C10 H10A . . 119.7 ?
C11 C10 H10A . . 119.7 ?
C12 C11 C10 . . 120.9(3) ?
C12 C11 N3 . . 121.5(3) ?
C10 C11 N3 . . 117.7(3) ?
O5 C12 C11 . . 125.7(3) ?
O5 C12 C13 . . 116.5(3) ?
C11 C12 C13 . . 117.8(3) ?
C14 C13 C12 . . 121.4(3) ?
C14 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
C13 C14 C9 . . 121.1(3) ?
C13 C14 H14 . . 119.5 ?
C9 C14 H14 . . 119.5 ?
C20 C15 C16 . . 117.6(3) ?
C20 C15 C21 . . 116.3(2) ?
C16 C15 C21 . . 126.0(3) ?
O6 C16 C17 . . 120.3(2) ?
O6 C16 C15 . . 119.7(3) ?
C17 C16 C15 . . 120.0(3) ?
C18 C17 C16 . . 120.6(3) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C17 C18 C19 . . 120.5(3) ?
C17 C18 H18 . . 119.7 ?
C19 C18 H18 . . 119.7 ?
C20 C19 C18 . . 119.1(3) ?
C20 C19 H19 . . 120.4 ?
C18 C19 H19 . . 120.4 ?
C19 C20 C15 . . 122.1(3) ?
C19 C20 H20 . . 119.0 ?
C15 C20 H20 . . 119.0 ?
O7 C21 N4 . . 121.9(3) ?
O7 C21 C15 . . 121.3(3) ?
N4 C21 C15 . . 116.7(2) ?
N5 C22 C23 . . 124.4(3) ?
N5 C22 H22 . . 117.8 ?
C23 C22 H22 . . 117.8 ?
C24 C23 C28 . . 117.6(3) ?
C24 C23 C22 . . 118.7(3) ?
C28 C23 C22 . . 123.6(3) ?
C23 C24 C25 . . 121.5(3) ?
C23 C24 H24 . . 119.2 ?
C25 C24 H24 . . 119.2 ?
C24 C25 C26 . . 120.6(3) ?
C24 C25 N6 . . 117.8(3) ?
C26 C25 N6 . . 121.6(3) ?
O10 C26 C27 . . 117.7(3) ?
O10 C26 C25 . . 124.6(3) ?
C27 C26 C25 . . 117.7(3) ?
C28 C27 C26 . . 121.7(3) ?
C28 C27 H27 . . 119.2 ?
C26 C27 H27 . . 119.2 ?
C27 C28 C23 . . 120.8(3) ?
C27 C28 H28 . . 119.6 ?
C23 C28 H28 . . 119.6 ?
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 C2 . 1.361(3) ?
O1 H1A . 0.8200 ?
O2 C7 . 1.224(3) ?
O3 N3 . 1.211(3) ?
O4 N3 . 1.217(3) ?
O5 C12 . 1.344(3) ?
O5 H5 . 0.8200 ?
O6 C16 . 1.359(3) ?
O6 H6 . 0.8200 ?
O7 C21 . 1.227(3) ?
O8 N6 . 1.213(3) ?
O9 N6 . 1.235(3) ?
O10 C26 . 1.337(3) ?
O10 H10 . 0.8200 ?
N1 C7 . 1.346(3) ?
N1 N2 . 1.377(3) ?
N1 H1 . 0.898(10) ?
N2 C8 . 1.269(3) ?
N3 C11 . 1.439(4) ?
N4 C21 . 1.342(4) ?
N4 N5 . 1.377(3) ?
N4 H4 . 0.903(10) ?
N5 C22 . 1.266(4) ?
N6 C25 . 1.438(4) ?
C1 C6 . 1.393(4) ?
C1 C2 . 1.398(4) ?
C1 C7 . 1.490(4) ?
C2 C3 . 1.385(4) ?
C3 C4 . 1.361(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.370(4) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C8 C9 . 1.454(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.377(4) ?
C9 C14 . 1.400(4) ?
C10 C11 . 1.391(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.389(4) ?
C12 C13 . 1.391(4) ?
C13 C14 . 1.358(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C20 . 1.397(4) ?
C15 C16 . 1.399(4) ?
C15 C21 . 1.491(4) ?
C16 C17 . 1.381(4) ?
C17 C18 . 1.373(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.374(4) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.369(4) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C22 C23 . 1.446(4) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.371(4) ?
C23 C28 . 1.407(4) ?
C24 C25 . 1.384(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.394(4) ?
C26 C27 . 1.383(4) ?
C27 C28 . 1.364(4) ?
C27 H27 . 0.9300 ?
C28 H28 . 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 H1A O7 1_545 0.82 1.86 2.650(3) 162
O5 H5 O4 . 0.82 1.94 2.621(3) 140
O5 H5 O4 3_666 0.82 2.30 2.997(3) 143
O5 H5 N3 . 0.82 2.51 2.928(3) 112
O6 H6 O2 . 0.82 1.91 2.713(3) 168
O10 H10 O9 . 0.82 1.91 2.596(3) 140
O10 H10 N6 . 0.82 2.50 2.909(4) 112
N4 H4 O6 . 0.903(10) 1.93(3) 2.640(3) 134(3)
N1 H1 O1 . 0.898(10) 1.84(2) 2.599(3) 141(3)
