#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/80/2218076.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_2218076
loop_
_publ_author_name
'Han, Ling'
'Huang, Shan-Shan'
'Huang, Qing-Bai'
'Zhou, Xue-Mei'
'Diao, Yun-Peng'
_publ_section_title
;
 N'-(2-Hydroxy-5-chlorobenzylidene)-4-nitrobenzohydrazide
 methanol solvate
;
_journal_coeditor_code           CI2574
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o781
_journal_paper_doi               10.1107/S160053680800843X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H10 Cl N3 O4, C H4 O'
_chemical_formula_moiety         'C14 H10 Cl N3 O4, C H4 O'
_chemical_formula_sum            'C15 H14 Cl N3 O5'
_chemical_formula_weight         351.74
_chemical_name_systematic
;
N'-(2-Hydroxy-5-chlorobenzylidene)-4-nitrobenzohydrazide methanol
solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.29(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6280(10)
_cell_length_b                   18.980(3)
_cell_length_c                   12.521(2)
_cell_measurement_reflns_used    1014
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      2.5
_cell_volume                     1574.7(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 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  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9258
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.9548
_exptl_absorpt_correction_T_min  0.9472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0546
_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)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                1776
_reflns_number_total             3259
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2574.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218076
_cod_database_fobs_code          2218076
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl Cl1 0.68929(13) 0.04557(4) 0.92197(7) 0.0738(3) Uani d . 1
N N1 0.5353(5) 0.73926(13) 0.88443(19) 0.0595(7) Uani d . 1
N N2 0.8868(3) 0.42344(11) 0.86323(19) 0.0495(6) Uani d D 1
N N3 0.9879(3) 0.35976(11) 0.86989(17) 0.0478(6) Uani d . 1
O O1 0.3541(4) 0.73510(11) 0.89719(19) 0.0807(7) Uani d . 1
O O2 0.6246(4) 0.79469(11) 0.87488(19) 0.0824(7) Uani d . 1
O O3 1.1727(3) 0.48808(10) 0.86669(16) 0.0623(6) Uani d . 1
O O4 1.2997(3) 0.26460(10) 0.87161(18) 0.0659(6) Uani d . 1
H H4 1.2520 0.3044 0.8735 0.099 Uiso calc R 1
O O5 0.4676(3) 0.40021(11) 0.80587(18) 0.0674(6) Uani d . 1
H H5 0.3727 0.4232 0.8281 0.101 Uiso calc R 1
C C1 0.6514(4) 0.67373(13) 0.8806(2) 0.0470(7) Uani d . 1
C C2 0.5546(4) 0.61164(14) 0.9009(2) 0.0548(8) Uani d . 1
H H2 0.4187 0.6113 0.9177 0.066 Uiso calc R 1
C C3 0.6617(4) 0.54978(14) 0.8959(2) 0.0518(8) Uani d . 1
H H3 0.5977 0.5074 0.9108 0.062 Uiso calc R 1
C C4 0.8634(4) 0.54947(13) 0.8691(2) 0.0426(6) Uani d . 1
C C5 0.9558(4) 0.61350(14) 0.8499(2) 0.0521(7) Uani d . 1
H H5A 1.0915 0.6143 0.8327 0.063 Uiso calc R 1
C C6 0.8517(5) 0.67595(14) 0.8558(2) 0.0549(8) Uani d . 1
H H6 0.9156 0.7187 0.8432 0.066 Uiso calc R 1
C C7 0.9882(4) 0.48478(14) 0.8649(2) 0.0443(6) Uani d . 1
C C8 0.8723(4) 0.30647(14) 0.8789(2) 0.0488(7) Uani d . 1
H H8 0.7338 0.3140 0.8806 0.059 Uiso calc R 1
C C9 0.9467(4) 0.23460(13) 0.8868(2) 0.0443(7) Uani d . 1
C C10 1.1506(4) 0.21677(14) 0.8820(2) 0.0499(7) Uani d . 1
C C11 1.2063(5) 0.14648(15) 0.8879(3) 0.0635(9) Uani d . 1
H H11 1.3419 0.1344 0.8842 0.076 Uiso calc R 1
C C12 1.0660(5) 0.09492(15) 0.8992(2) 0.0607(8) Uani d . 1
H H12 1.1058 0.0480 0.9025 0.073 Uiso calc R 1
C C13 0.8651(4) 0.11224(14) 0.9058(2) 0.0503(7) Uani d . 1
C C14 0.8072(4) 0.18097(14) 0.8996(2) 0.0497(7) Uani d . 1
H H14 0.6711 0.1922 0.9042 0.060 Uiso calc R 1
C C15 0.4413(6) 0.38939(17) 0.6953(3) 0.0850(11) Uani d . 1
H H15A 0.3767 0.4298 0.6636 0.127 Uiso calc R 1
H H15B 0.3587 0.3485 0.6830 0.127 Uiso calc R 1
H H15C 0.5704 0.3824 0.6637 0.127 Uiso calc R 1
H H2A 0.7515(16) 0.4223(17) 0.856(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
O2 N1 O1 123.6(3)
O2 N1 C1 118.3(3)
O1 N1 C1 118.0(3)
C7 N2 N3 121.0(2)
C7 N2 H2A 121(2)
N3 N2 H2A 118(2)
C8 N3 N2 114.0(2)
C10 O4 H4 109.5
C15 O5 H5 109.5
C2 C1 C6 121.9(3)
C2 C1 N1 118.5(3)
C6 C1 N1 119.6(3)
C1 C2 C3 118.9(3)
C1 C2 H2 120.6
C3 C2 H2 120.6
C2 C3 C4 121.1(3)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 118.1(2)
C5 C4 C7 118.2(2)
C3 C4 C7 123.7(2)
C6 C5 C4 121.6(3)
C6 C5 H5A 119.2
C4 C5 H5A 119.2
C1 C6 C5 118.4(3)
C1 C6 H6 120.8
C5 C6 H6 120.8
O3 C7 N2 122.9(2)
O3 C7 C4 121.0(2)
N2 C7 C4 116.0(2)
N3 C8 C9 123.2(3)
N3 C8 H8 118.4
C9 C8 H8 118.4
C14 C9 C10 118.4(2)
C14 C9 C8 118.1(2)
C10 C9 C8 123.5(3)
O4 C10 C11 117.2(3)
O4 C10 C9 123.6(2)
C11 C10 C9 119.2(3)
C12 C11 C10 121.1(3)
C12 C11 H11 119.4
C10 C11 H11 119.4
C11 C12 C13 120.0(3)
C11 C12 H12 120.0
C13 C12 H12 120.0
C14 C13 C12 119.8(3)
C14 C13 Cl1 121.1(2)
C12 C13 Cl1 119.1(2)
C13 C14 C9 121.5(3)
C13 C14 H14 119.3
C9 C14 H14 119.3
O5 C15 H15A 109.5
O5 C15 H15B 109.5
H15A C15 H15B 109.5
O5 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C13 1.735(3)
N1 O2 1.215(3)
N1 O1 1.217(3)
N1 C1 1.464(3)
N2 C7 1.344(3)
N2 N3 1.384(3)
N2 H2A 0.899(10)
N3 C8 1.275(3)
O3 C7 1.225(3)
O4 C10 1.350(3)
O4 H4 0.82
O5 C15 1.407(4)
O5 H5 0.82
C1 C2 1.368(4)
C1 C6 1.371(4)
C2 C3 1.374(3)
C2 H2 0.93
C3 C4 1.386(4)
C3 H3 0.93
C4 C5 1.384(3)
C4 C7 1.482(4)
C5 C6 1.374(4)
C5 H5A 0.93
C6 H6 0.93
C8 C9 1.453(3)
C8 H8 0.93
C9 C14 1.387(4)
C9 C10 1.396(4)
C10 C11 1.386(4)
C11 C12 1.360(4)
C11 H11 0.93
C12 C13 1.375(4)
C12 H12 0.93
C13 C14 1.362(3)
C14 H14 0.93
C15 H15A 0.96
C15 H15B 0.96
C15 H15C 0.96
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
O4 H4 N3 . 0.82 2.04 2.745(3) 144
O4 H4 O5 1_655 0.82 2.47 2.930(3) 116
O5 H5 O3 1_455 0.82 1.88 2.692(3) 171
N2 H2A O5 . 0.899(10) 2.016(13) 2.888(3) 163(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194606
