#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/07/2230787.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_2230787
loop_
_publ_author_name
'Zhang, Zhen'
_publ_section_title
;
 3-Chloro-N'-(4-hydroxy-3-nitrobenzylidene)benzohydrazide
 methanol disolvate
;
_journal_coeditor_code           LH5265
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1630
_journal_paper_doi               10.1107/S1600536811021568
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H10 Cl N3 O4, 2C H4 O'
_chemical_formula_moiety         'C14 H10 Cl N3 O4, 2(C H4 O)'
_chemical_formula_sum            'C16 H18 Cl N3 O6'
_chemical_formula_weight         383.78
_chemical_name_systematic
;
3-Chloro-N'-(4-hydroxy-3-nitrobenzylidene)benzohydrazide methanol
disolvate
;
_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                 94.689(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.626(2)
_cell_length_b                   18.846(5)
_cell_length_c                   12.739(3)
_cell_measurement_reflns_used    954
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     1824.7(8)
_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  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_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  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0854
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7726
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9499
_exptl_absorpt_correction_T_min  0.9454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.0666
_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)+(0.0891P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.2082
_reflns_number_gt                1842
_reflns_number_total             3695
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5265.cif
_cod_data_source_block           I
_cod_original_cell_volume        1824.6(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230787
_cod_database_fobs_code          2230787
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.06078(17) -0.35391(5) 0.03312(9) 0.0708(4) Uani d . 1 1 . .
N N1 0.4832(5) 0.32118(17) -0.0141(3) 0.0546(9) Uani d . 1 1 . .
N N2 0.7478(4) 0.02147(15) 0.0491(2) 0.0526(9) Uani d . 1 1 . .
N N3 0.7737(5) -0.03895(16) -0.0091(2) 0.0518(9) Uani d D 1 1 . .
O O1 0.4617(5) 0.37833(14) 0.0290(2) 0.0781(10) Uani d . 1 1 . .
O O2 0.4421(4) 0.31188(15) -0.1072(2) 0.0768(10) Uani d . 1 1 . .
O O3 0.5851(4) 0.32945(13) 0.21283(19) 0.0652(9) Uani d . 1 1 . .
H H3A 0.5220 0.3575 0.1780 0.098 Uiso calc R 1 1 . .
O O4 0.8426(5) -0.10265(14) 0.1374(2) 0.0773(10) Uani d . 1 1 . .
O O5 0.3664(4) 0.45501(16) 0.2154(2) 0.0744(9) Uani d . 1 1 . .
H H5 0.3000 0.4414 0.2587 0.112 Uiso calc R 1 1 . .
O O6 0.6850(6) 0.5111(2) 0.2745(3) 0.1082(14) Uani d . 1 1 . .
H H6 0.5888 0.4937 0.2563 0.162 Uiso calc R 1 1 . .
C C1 0.6684(5) 0.14309(18) 0.0505(3) 0.0474(10) Uani d . 1 1 . .
C C2 0.5915(5) 0.19991(18) -0.0036(3) 0.0452(9) Uani d . 1 1 . .
H H2 0.5575 0.1957 -0.0751 0.054 Uiso calc R 1 1 . .
C C3 0.5644(5) 0.26316(18) 0.0480(3) 0.0437(9) Uani d . 1 1 . .
C C4 0.6108(5) 0.27168(19) 0.1552(3) 0.0482(10) Uani d . 1 1 . .
C C5 0.6913(6) 0.2144(2) 0.2073(3) 0.0566(11) Uani d . 1 1 . .
H H5A 0.7265 0.2186 0.2787 0.068 Uiso calc R 1 1 . .
C C6 0.7208(6) 0.1523(2) 0.1581(3) 0.0559(11) Uani d . 1 1 . .
H H6A 0.7765 0.1153 0.1959 0.067 Uiso calc R 1 1 . .
C C7 0.6967(5) 0.07624(19) -0.0032(3) 0.0530(10) Uani d . 1 1 . .
H H7 0.6772 0.0736 -0.0761 0.064 Uiso calc R 1 1 . .
C C8 0.8224(5) -0.09925(19) 0.0410(3) 0.0495(10) Uani d . 1 1 . .
C C9 0.8502(5) -0.16287(17) -0.0252(3) 0.0402(9) Uani d . 1 1 . .
C C10 0.9332(5) -0.22067(18) 0.0246(3) 0.0459(9) Uani d . 1 1 . .
H H10 0.9724 -0.2180 0.0956 0.055 Uiso calc R 1 1 . .
C C11 0.9576(5) -0.28200(18) -0.0311(3) 0.0452(9) Uani d . 1 1 . .
C C12 0.9009(5) -0.2878(2) -0.1355(3) 0.0543(11) Uani d . 1 1 . .
H H12 0.9173 -0.3296 -0.1722 0.065 Uiso calc R 1 1 . .
C C13 0.8189(6) -0.2303(2) -0.1848(3) 0.0564(11) Uani d . 1 1 . .
H H13 0.7805 -0.2333 -0.2558 0.068 Uiso calc R 1 1 . .
C C14 0.7929(5) -0.16866(19) -0.1309(3) 0.0498(10) Uani d . 1 1 . .
H H14 0.7365 -0.1305 -0.1656 0.060 Uiso calc R 1 1 . .
H H3 0.771(5) -0.0374(19) -0.0792(9) 0.060 Uiso d D 1 1 . .
C C15 0.2719(8) 0.4968(2) 0.1385(4) 0.0930(17) Uani d . 1 1 . .
H H15A 0.2107 0.5338 0.1724 0.139 Uiso calc R 1 1 . .
H H15B 0.1885 0.4676 0.0979 0.139 Uiso calc R 1 1 . .
H H15C 0.3520 0.5175 0.0929 0.139 Uiso calc R 1 1 . .
C C16 0.7983(9) 0.5025(3) 0.1930(5) 0.132(2) Uani d . 1 1 . .
H H16A 0.7729 0.5382 0.1402 0.198 Uiso calc R 1 1 . .
H H16B 0.7808 0.4563 0.1620 0.198 Uiso calc R 1 1 . .
H H16C 0.9183 0.5071 0.2215 0.198 Uiso calc R 1 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
O2 N1 O1 . . 122.1(3) ?
O2 N1 C3 . . 119.1(3) ?
O1 N1 C3 . . 118.8(3) ?
C7 N2 N3 . . 116.0(3) ?
C8 N3 N2 . . 119.3(3) ?
C8 N3 H3 . . 119(2) ?
N2 N3 H3 . . 121(2) ?
C4 O3 H3A . . 109.5 ?
C15 O5 H5 . . 109.5 ?
C16 O6 H6 . . 109.5 ?
C2 C1 C6 . . 117.8(3) ?
C2 C1 C7 . . 120.7(3) ?
C6 C1 C7 . . 121.5(3) ?
C1 C2 C3 . . 120.4(3) ?
C1 C2 H2 . . 119.8 ?
C3 C2 H2 . . 119.8 ?
C2 C3 C4 . . 122.0(3) ?
C2 C3 N1 . . 117.5(3) ?
C4 C3 N1 . . 120.6(3) ?
O3 C4 C5 . . 116.8(3) ?
O3 C4 C3 . . 126.6(3) ?
C5 C4 C3 . . 116.6(3) ?
C6 C5 C4 . . 122.4(4) ?
C6 C5 H5A . . 118.8 ?
C4 C5 H5A . . 118.8 ?
C5 C6 C1 . . 120.9(3) ?
C5 C6 H6A . . 119.6 ?
C1 C6 H6A . . 119.6 ?
N2 C7 C1 . . 120.4(3) ?
N2 C7 H7 . . 119.8 ?
C1 C7 H7 . . 119.8 ?
O4 C8 N3 . . 121.8(3) ?
O4 C8 C9 . . 120.8(3) ?
N3 C8 C9 . . 117.4(3) ?
C14 C9 C10 . . 118.6(3) ?
C14 C9 C8 . . 124.4(3) ?
C10 C9 C8 . . 117.0(3) ?
C11 C10 C9 . . 119.9(3) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C12 C11 C10 . . 121.5(3) ?
C12 C11 Cl1 . . 119.3(3) ?
C10 C11 Cl1 . . 119.1(3) ?
C11 C12 C13 . . 118.4(3) ?
C11 C12 H12 . . 120.8 ?
C13 C12 H12 . . 120.8 ?
C14 C13 C12 . . 121.2(4) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C13 C14 C9 . . 120.4(3) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
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 ?
O6 C16 H16A . . 109.5 ?
O6 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O6 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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 C11 . 1.738(3) ?
N1 O2 . 1.214(4) ?
N1 O1 . 1.226(4) ?
N1 C3 . 1.458(4) ?
N2 C7 . 1.272(4) ?
N2 N3 . 1.382(4) ?
N3 C8 . 1.341(4) ?
N3 H3 . 0.893(10) ?
O3 C4 . 1.336(4) ?
O3 H3A . 0.8200 ?
O4 C8 . 1.227(4) ?
O5 C15 . 1.409(5) ?
O5 H5 . 0.8200 ?
O6 C16 . 1.413(6) ?
O6 H6 . 0.8200 ?
C1 C2 . 1.378(5) ?
C1 C6 . 1.406(5) ?
C1 C7 . 1.458(5) ?
C2 C3 . 1.385(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.392(5) ?
C4 C5 . 1.385(5) ?
C5 C6 . 1.355(5) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.491(5) ?
C9 C14 . 1.386(5) ?
C9 C10 . 1.387(4) ?
C10 C11 . 1.377(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.369(5) ?
C12 C13 . 1.377(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.371(5) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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 H3A O1 . 0.82 1.96 2.618(4) 137
O3 H3A O5 . 0.82 2.26 2.896(4) 135
O6 H6 O5 . 0.82 1.88 2.700(5) 179
N3 H3 O6 4_565 0.893(10) 1.988(18) 2.834(4) 158(4)
O5 H5 O4 2_655 0.82 1.96 2.779(4) 173
