#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/35/2223509.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_2223509
loop_
_publ_author_name
'Cao, Guo-Biao'
_publ_section_title
;
 (E)-4-Chloro-N'-(5-hydroxy-2-nitrobenzylidene)benzohydrazide
;
_journal_coeditor_code           OM2273
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2415
_journal_paper_doi               10.1107/S1600536809035740
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H10 Cl N3 O4'
_chemical_formula_moiety         'C14 H10 Cl N3 O4'
_chemical_formula_sum            'C14 H10 Cl N3 O4'
_chemical_formula_weight         319.70
_chemical_name_systematic
;
(E)-4-Chloro-N'-(5-hydroxy-2-nitrobenzylidene)benzohydrazide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.820(3)
_cell_angle_beta                 106.056(2)
_cell_angle_gamma                109.014(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5386(2)
_cell_length_b                   8.1677(2)
_cell_length_c                   12.3435(4)
_cell_measurement_reflns_used    2079
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      2.6
_cell_volume                     685.95(4)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART 1K'
_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  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4267
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_correction_T_min  0.9339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.366
_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     203
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0414
_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)+(0.051P)²+0.2581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                2444
_reflns_number_total             2933
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2273.cif
_cod_data_source_block           I
_cod_database_code               2223509
_cod_database_fobs_code          2223509
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl1 1.99310(8) 1.22131(10) 1.02766(6) 0.0873(3) Uani d . 1 . .
N N1 0.89654(18) 0.85347(17) 0.58743(11) 0.0363(3) Uani d . 1 . .
N N2 1.08279(18) 0.88906(18) 0.65933(12) 0.0365(3) Uani d D 1 . .
N N3 0.6482(2) 0.46355(18) 0.30087(13) 0.0424(3) Uani d . 1 . .
O O1 0.7870(2) 0.43682(18) 0.36768(12) 0.0570(4) Uani d . 1 . .
O O2 0.5932(3) 0.4105(2) 0.20048(13) 0.0756(5) Uani d . 1 . .
O O3 0.22232(17) 0.82467(17) 0.43739(11) 0.0489(3) Uani d . 1 . .
H H3 0.1313 0.8286 0.3839 0.073 Uiso calc R 1 . .
O O4 1.08646(17) 1.14913(16) 0.72801(11) 0.0458(3) Uani d . 1 . .
C C1 0.6246(2) 0.67228(19) 0.44254(13) 0.0299(3) Uani d . 1 . .
C C2 0.5411(2) 0.55749(19) 0.34209(13) 0.0332(3) Uani d . 1 . .
C C3 0.3510(2) 0.5302(2) 0.27424(14) 0.0407(4) Uani d . 1 . .
H H3A 0.2995 0.4535 0.2079 0.049 Uiso calc R 1 . .
C C4 0.2379(2) 0.6149(2) 0.30395(15) 0.0407(4) Uani d . 1 . .
H H4 0.1098 0.5944 0.2590 0.049 Uiso calc R 1 . .
C C5 0.3180(2) 0.7317(2) 0.40214(14) 0.0352(3) Uani d . 1 . .
C C6 0.5077(2) 0.75750(19) 0.46992(13) 0.0322(3) Uani d . 1 . .
H H6 0.5584 0.8346 0.5361 0.039 Uiso calc R 1 . .
C C7 0.8272(2) 0.7162(2) 0.51835(13) 0.0326(3) Uani d . 1 . .
H H7 0.9012 0.6456 0.5154 0.039 Uiso calc R 1 . .
C C8 1.1687(2) 1.0418(2) 0.72753(13) 0.0337(3) Uani d . 1 . .
C C9 1.3720(2) 1.0754(2) 0.80277(13) 0.0335(3) Uani d . 1 . .
C C10 1.4371(3) 1.1911(2) 0.90032(14) 0.0438(4) Uani d . 1 . .
H H10 1.3523 1.2403 0.9185 0.053 Uiso calc R 1 . .
C C11 1.6278(3) 1.2339(3) 0.97075(15) 0.0511(5) Uani d . 1 . .
H H11 1.6716 1.3107 1.0366 0.061 Uiso calc R 1 . .
C C12 1.7510(3) 1.1612(3) 0.94169(15) 0.0474(4) Uani d . 1 . .
C C13 1.6913(2) 1.0459(2) 0.84568(15) 0.0437(4) Uani d . 1 . .
H H13 1.7774 0.9981 0.8278 0.052 Uiso calc R 1 . .
C C14 1.5000(2) 1.0026(2) 0.77637(14) 0.0362(3) Uani d . 1 . .
H H14 1.4565 0.9239 0.7115 0.043 Uiso calc R 1 . .
H H2 1.141(3) 0.809(2) 0.660(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'
Cl Cl 0.1484 0.1585 '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 . . 116.59(12) ?
C8 N2 N1 . . 118.41(12) ?
C8 N2 H2 . . 122.9(16) ?
N1 N2 H2 . . 118.7(16) ?
O2 N3 O1 . . 121.99(15) ?
O2 N3 C2 . . 118.32(15) ?
O1 N3 C2 . . 119.67(14) ?
C5 O3 H3 . . 109.5 ?
C6 C1 C2 . . 116.51(13) ?
C6 C1 C7 . . 117.54(13) ?
C2 C1 C7 . . 125.89(13) ?
C3 C2 C1 . . 121.43(14) ?
C3 C2 N3 . . 115.96(14) ?
C1 C2 N3 . . 122.59(14) ?
C4 C3 C2 . . 120.83(15) ?
C4 C3 H3A . . 119.6 ?
C2 C3 H3A . . 119.6 ?
C3 C4 C5 . . 119.00(14) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
O3 C5 C6 . . 116.31(14) ?
O3 C5 C4 . . 123.86(14) ?
C6 C5 C4 . . 119.83(14) ?
C5 C6 C1 . . 122.38(14) ?
C5 C6 H6 . . 118.8 ?
C1 C6 H6 . . 118.8 ?
N1 C7 C1 . . 117.56(13) ?
N1 C7 H7 . . 121.2 ?
C1 C7 H7 . . 121.2 ?
O4 C8 N2 . . 122.68(14) ?
O4 C8 C9 . . 120.98(14) ?
N2 C8 C9 . . 116.33(13) ?
C10 C9 C14 . . 119.36(14) ?
C10 C9 C8 . . 117.71(14) ?
C14 C9 C8 . . 122.85(14) ?
C11 C10 C9 . . 120.34(16) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C12 C11 C10 . . 118.85(16) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
C11 C12 C13 . . 122.33(16) ?
C11 C12 Cl1 . . 118.73(14) ?
C13 C12 Cl1 . . 118.92(15) ?
C12 C13 C14 . . 118.43(16) ?
C12 C13 H13 . . 120.8 ?
C14 C13 H13 . . 120.8 ?
C13 C14 C9 . . 120.67(15) ?
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
Cl1 C12 . 1.7399(17) ?
N1 C7 . 1.266(2) ?
N1 N2 . 1.3714(17) ?
N2 C8 . 1.351(2) ?
N2 H2 . 0.896(10) ?
N3 O2 . 1.2160(19) ?
N3 O1 . 1.2245(19) ?
N3 C2 . 1.456(2) ?
O3 C5 . 1.3447(19) ?
O3 H3 . 0.8200 ?
O4 C8 . 1.2285(18) ?
C1 C6 . 1.391(2) ?
C1 C2 . 1.401(2) ?
C1 C7 . 1.476(2) ?
C2 C3 . 1.388(2) ?
C3 C4 . 1.375(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.389(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(2) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.489(2) ?
C9 C10 . 1.387(2) ?
C9 C14 . 1.390(2) ?
C10 C11 . 1.385(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.372(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(3) ?
C13 C14 . 1.383(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
O3 H3 O4 2_676 0.82 1.89 2.7093(17) 173.7
N2 H2 O1 2_766 0.896(10) 2.290(11) 3.1649(18) 165(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5694927
