#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/49/2224917.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_2224917
loop_
_publ_author_name
'Zhou, Cong-Shan'
'Yang, Tao'
_publ_section_title
;
 2-Chloro-N'-(5-hydroxy-2-nitrobenzylidene)benzohydrazide
;
_journal_coeditor_code           CI5018
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o365
_journal_paper_doi               10.1107/S1600536810001303
_journal_volume                  66
_journal_year                    2010
_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
;
2-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                100.623(2)
_cell_angle_beta                 97.433(2)
_cell_angle_gamma                96.127(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2490(2)
_cell_length_b                   9.4719(3)
_cell_length_c                   10.4749(4)
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.6
_cell_volume                     694.64(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 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4097
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.9567
_exptl_absorpt_correction_T_min  0.9511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0369
_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)+(0.0433P)²+0.2231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                2332
_reflns_number_total             2900
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5018.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224917
_cod_database_fobs_code          2224917
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 0.21511(7) 0.78685(7) 0.05703(5) 0.06308(19) Uani d . 1 . .
N N1 0.2273(2) 0.77176(15) 0.47983(14) 0.0378(3) Uani d . 1 . .
N N2 0.3525(2) 0.78387(15) 0.39232(15) 0.0387(3) Uani d D 1 . .
N N3 0.3042(2) 0.46714(16) 0.72546(17) 0.0469(4) Uani d . 1 . .
O O1 0.30056(19) 1.01035(13) 0.37374(13) 0.0487(3) Uani d . 1 . .
O O2 0.3739(2) 0.42683(16) 0.62639(16) 0.0618(4) Uani d . 1 . .
O O3 0.3681(2) 0.44819(19) 0.83292(17) 0.0740(5) Uani d . 1 . .
O O4 -0.33418(18) 0.74516(14) 0.71890(14) 0.0501(3) Uani d . 1 . .
H H4 -0.3206 0.8188 0.6885 0.075 Uiso calc R 1 . .
C C1 0.1112(2) 0.63648(17) 0.62866(16) 0.0356(4) Uani d . 1 . .
C C2 0.1367(2) 0.54064(17) 0.71438(17) 0.0370(4) Uani d . 1 . .
C C3 0.0078(3) 0.51237(18) 0.79603(18) 0.0427(4) Uani d . 1 . .
H H3 0.0290 0.4480 0.8518 0.051 Uiso calc R 1 . .
C C4 -0.1514(3) 0.57918(19) 0.79491(18) 0.0418(4) Uani d . 1 . .
H H4A -0.2407 0.5575 0.8471 0.050 Uiso calc R 1 . .
C C5 -0.1775(2) 0.67960(18) 0.71488(17) 0.0381(4) Uani d . 1 . .
C C6 -0.0480(2) 0.70698(18) 0.63260(17) 0.0372(4) Uani d . 1 . .
H H6 -0.0679 0.7737 0.5790 0.045 Uiso calc R 1 . .
C C7 0.2412(2) 0.66589(18) 0.53720(18) 0.0396(4) Uani d . 1 . .
H H7 0.3336 0.6068 0.5214 0.047 Uiso calc R 1 . .
C C8 0.3786(2) 0.90324(17) 0.34225(16) 0.0342(4) Uani d . 1 . .
C C9 0.5138(2) 0.89383(17) 0.24509(17) 0.0352(4) Uani d . 1 . .
C C10 0.4520(2) 0.84446(18) 0.11239(18) 0.0391(4) Uani d . 1 . .
C C11 0.5744(3) 0.8381(2) 0.02143(19) 0.0480(5) Uani d . 1 . .
H H11 0.5302 0.8060 -0.0677 0.058 Uiso calc R 1 . .
C C12 0.7634(3) 0.8801(2) 0.0653(2) 0.0551(5) Uani d . 1 . .
H H12 0.8473 0.8770 0.0051 0.066 Uiso calc R 1 . .
C C13 0.8291(3) 0.9268(2) 0.1973(2) 0.0598(6) Uani d . 1 . .
H H13 0.9571 0.9537 0.2260 0.072 Uiso calc R 1 . .
C C14 0.7048(3) 0.9337(2) 0.2875(2) 0.0497(5) Uani d . 1 . .
H H14 0.7495 0.9651 0.3767 0.060 Uiso calc R 1 . .
H H2 0.421(3) 0.713(2) 0.373(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 . . 114.29(13) ?
C8 N2 N1 . . 121.18(13) ?
C8 N2 H2 . . 119.8(16) ?
N1 N2 H2 . . 119.0(16) ?
O3 N3 O2 . . 122.61(16) ?
O3 N3 C2 . . 118.25(16) ?
O2 N3 C2 . . 119.14(16) ?
C5 O4 H4 . . 109.5 ?
C6 C1 C2 . . 116.75(14) ?
C6 C1 C7 . . 119.39(14) ?
C2 C1 C7 . . 123.86(15) ?
C3 C2 C1 . . 122.08(15) ?
C3 C2 N3 . . 115.99(15) ?
C1 C2 N3 . . 121.91(15) ?
C4 C3 C2 . . 120.15(15) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 119.29(15) ?
C3 C4 H4A . . 120.4 ?
C5 C4 H4A . . 120.4 ?
O4 C5 C6 . . 122.39(15) ?
O4 C5 C4 . . 117.36(15) ?
C6 C5 C4 . . 120.23(15) ?
C5 C6 C1 . . 121.40(15) ?
C5 C6 H6 . . 119.3 ?
C1 C6 H6 . . 119.3 ?
N1 C7 C1 . . 120.03(14) ?
N1 C7 H7 . . 120.0 ?
C1 C7 H7 . . 120.0 ?
O1 C8 N2 . . 123.19(14) ?
O1 C8 C9 . . 123.39(14) ?
N2 C8 C9 . . 113.42(13) ?
C10 C9 C14 . . 118.64(15) ?
C10 C9 C8 . . 121.08(15) ?
C14 C9 C8 . . 120.28(16) ?
C9 C10 C11 . . 121.74(17) ?
C9 C10 Cl1 . . 119.70(12) ?
C11 C10 Cl1 . . 118.56(15) ?
C12 C11 C10 . . 118.78(18) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
C13 C12 C11 . . 120.62(17) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C14 . . 120.08(19) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C13 C14 C9 . . 120.11(19) ?
C13 C14 H14 . . 119.9 ?
C9 C14 H14 . . 119.9 ?
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 C10 . 1.7346(18) ?
N1 C7 . 1.267(2) ?
N1 N2 . 1.3814(18) ?
N2 C8 . 1.337(2) ?
N2 H2 . 0.891(10) ?
N3 O3 . 1.213(2) ?
N3 O2 . 1.228(2) ?
N3 C2 . 1.465(2) ?
O1 C8 . 1.2268(19) ?
O4 C5 . 1.353(2) ?
O4 H4 . 0.82 ?
C1 C6 . 1.395(2) ?
C1 C2 . 1.399(2) ?
C1 C7 . 1.470(2) ?
C2 C3 . 1.384(2) ?
C3 C4 . 1.374(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.391(2) ?
C4 H4A . 0.93 ?
C5 C6 . 1.390(2) ?
C6 H6 . 0.93 ?
C7 H7 . 0.93 ?
C8 C9 . 1.500(2) ?
C9 C10 . 1.381(2) ?
C9 C14 . 1.387(3) ?
C10 C11 . 1.381(2) ?
C11 C12 . 1.378(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.376(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.385(3) ?
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
N2 H2 O2 2_666 0.890(10) 2.090(10) 2.9591(18) 165(2)
O4 H4 O1 2_576 0.82 1.85 2.6708(17) 176
C7 H7 O2 . 0.93 2.22 2.817(2) 122
