#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/80/2228001.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_2228001
loop_
_publ_author_name
'Dai, Chun-Hua'
'Mao, Fu-Lin'
_publ_section_title
;
 N'-(4-Hydroxybenzylidene)-4-nitrobenzohydrazide
;
_journal_coeditor_code           SJ5045
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2942
_journal_paper_doi               10.1107/S1600536810042364
_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'-(4-Hydroxybenzylidene)-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                 95.748(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.856(3)
_cell_length_b                   13.368(5)
_cell_length_c                   12.527(5)
_cell_measurement_reflns_used    1632
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.2
_cell_volume                     1309.0(9)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7505
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0447
_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)+(0.0494P)²+0.1504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                1736
_reflns_number_total             2822
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5045.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228001
_cod_database_fobs_code          2228001
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
N N1 0.20526(19) -0.05033(11) 0.04617(11) 0.0433(4) Uani d . 1 . .
N N2 0.2594(2) 0.02540(11) -0.01727(11) 0.0420(4) Uani d D 1 . .
N N3 0.4845(2) 0.44506(12) -0.22229(13) 0.0510(4) Uani d . 1 . .
O O1 0.0039(2) -0.46112(9) 0.25453(11) 0.0598(4) Uani d . 1 . .
H H1 -0.0521 -0.4411 0.3021 0.090 Uiso calc R 1 . .
O O2 0.17995(17) 0.13969(9) 0.09997(10) 0.0512(4) Uani d . 1 . .
O O3 0.4755(2) 0.52833(11) -0.18407(13) 0.0872(6) Uani d . 1 . .
O O4 0.54671(18) 0.42836(10) -0.30610(10) 0.0603(4) Uani d . 1 . .
C C1 0.1654(2) -0.22332(13) 0.07612(14) 0.0395(4) Uani d . 1 . .
C C2 0.1046(2) -0.20626(13) 0.17594(14) 0.0433(5) Uani d . 1 . .
H H2A 0.1006 -0.1412 0.2020 0.052 Uiso calc R 1 . .
C C3 0.0511(2) -0.28366(13) 0.23572(14) 0.0444(5) Uani d . 1 . .
H H3 0.0107 -0.2708 0.3017 0.053 Uiso calc R 1 . .
C C4 0.0567(2) -0.38146(13) 0.19834(14) 0.0424(5) Uani d . 1 . .
C C5 0.1185(2) -0.39987(13) 0.10044(15) 0.0463(5) Uani d . 1 . .
H H5 0.1240 -0.4651 0.0753 0.056 Uiso calc R 1 . .
C C6 0.1721(2) -0.32147(13) 0.04010(14) 0.0446(5) Uani d . 1 . .
H H6 0.2132 -0.3346 -0.0256 0.053 Uiso calc R 1 . .
C C7 0.2197(2) -0.13939(13) 0.01282(14) 0.0422(4) Uani d . 1 . .
H H7 0.2649 -0.1512 -0.0519 0.051 Uiso calc R 1 . .
C C8 0.2426(2) 0.12013(13) 0.01678(13) 0.0372(4) Uani d . 1 . .
C C9 0.3070(2) 0.20201(12) -0.05002(13) 0.0352(4) Uani d . 1 . .
C C10 0.2986(2) 0.29875(13) -0.01120(14) 0.0454(5) Uani d . 1 . .
H H10 0.2541 0.3099 0.0538 0.055 Uiso calc R 1 . .
C C11 0.3552(2) 0.37861(13) -0.06733(15) 0.0482(5) Uani d . 1 . .
H H11 0.3492 0.4435 -0.0411 0.058 Uiso calc R 1 . .
C C12 0.4209(2) 0.36016(13) -0.16304(14) 0.0395(4) Uani d . 1 . .
C C13 0.4312(2) 0.26543(14) -0.20412(14) 0.0449(5) Uani d . 1 . .
H H13 0.4760 0.2548 -0.2691 0.054 Uiso calc R 1 . .
C C14 0.3738(2) 0.18647(13) -0.14713(14) 0.0446(5) Uani d . 1 . .
H H14 0.3799 0.1219 -0.1740 0.054 Uiso calc R 1 . .
H H2 0.299(3) 0.0083(16) -0.0797(11) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 . . 117.08(14) ?
C8 N2 N1 . . 117.50(13) ?
C8 N2 H2 . . 124.6(15) ?
N1 N2 H2 . . 117.9(15) ?
O3 N3 O4 . . 123.30(16) ?
O3 N3 C12 . . 118.13(16) ?
O4 N3 C12 . . 118.55(16) ?
C4 O1 H1 . . 109.5 ?
C6 C1 C2 . . 118.08(16) ?
C6 C1 C7 . . 121.71(15) ?
C2 C1 C7 . . 120.20(16) ?
C3 C2 C1 . . 121.08(16) ?
C3 C2 H2A . . 119.5 ?
C1 C2 H2A . . 119.5 ?
C2 C3 C4 . . 120.32(16) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
O1 C4 C5 . . 118.02(16) ?
O1 C4 C3 . . 122.60(15) ?
C5 C4 C3 . . 119.38(16) ?
C6 C5 C4 . . 120.15(17) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C1 . . 120.97(16) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
N1 C7 C1 . . 120.02(15) ?
N1 C7 H7 . . 120.0 ?
C1 C7 H7 . . 120.0 ?
O2 C8 N2 . . 122.05(15) ?
O2 C8 C9 . . 120.45(15) ?
N2 C8 C9 . . 117.49(14) ?
C10 C9 C14 . . 118.85(15) ?
C10 C9 C8 . . 117.14(14) ?
C14 C9 C8 . . 124.01(15) ?
C11 C10 C9 . . 121.04(16) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C12 C11 C10 . . 118.37(17) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
C13 C12 C11 . . 122.28(16) ?
C13 C12 N3 . . 119.15(15) ?
C11 C12 N3 . . 118.56(16) ?
C12 C13 C14 . . 118.62(15) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C13 C14 C9 . . 120.83(16) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 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
N1 C7 . 1.271(2) ?
N1 N2 . 1.3803(19) ?
N2 C8 . 1.347(2) ?
N2 H2 . 0.899(9) ?
N3 O3 . 1.217(2) ?
N3 O4 . 1.2220(19) ?
N3 C12 . 1.471(2) ?
O1 C4 . 1.364(2) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.2247(19) ?
C1 C6 . 1.390(2) ?
C1 C2 . 1.401(2) ?
C1 C7 . 1.462(2) ?
C2 C3 . 1.368(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.391(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(2) ?
C5 C6 . 1.382(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.496(2) ?
C9 C10 . 1.386(2) ?
C9 C14 . 1.388(2) ?
C10 C11 . 1.376(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.374(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.372(2) ?
C13 C14 . 1.375(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
O1 H1 O2 2_545 0.82 1.98 2.7841(18) 165.8
N2 H2 O4 2_644 0.899(9) 2.239(12) 3.094(2) 158.9(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12972746
