#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/10/2221032.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_2221032
loop_
_publ_author_name
'Xiao, Ge-Jiang'
'Wei, Chao'
_publ_section_title
;
 N'-[1-(2-Hydroxyphenyl)ethylidene]-2-nitrobenzohydrazide
 methanol solvate
;
_journal_coeditor_code           CI2770
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o585
_journal_paper_doi               10.1107/S160053680900508X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H13 N3 O4, C H4 O'
_chemical_formula_moiety         'C15 H13 N3 O4, C H4 O'
_chemical_formula_sum            'C16 H17 N3 O5'
_chemical_formula_weight         331.33
_chemical_name_systematic
;
N'-[1-(2-Hydroxyphenyl)ethylidene]-2-nitrobenzohydrazide methanol
solvate
;
_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                101.950(2)
_cell_angle_beta                 92.972(2)
_cell_angle_gamma                114.889(2)
_cell_formula_units_Z            2
_cell_length_a                   7.124(2)
_cell_length_b                   8.066(2)
_cell_length_c                   15.764(3)
_cell_measurement_reflns_used    1968
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.6
_cell_volume                     794.0(3)
_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 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4659
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.228
_refine_ls_extinction_coef       0.066(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0434
_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)+(0.0585P)²+0.1607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                2660
_reflns_number_total             3371
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2770.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               2221032
_cod_database_fobs_code          2221032
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
O O1 0.46363(18) 0.2874(2) 0.22886(7) 0.0558(3) Uani d . 1 . .
O O2 0.2215(3) 0.7197(2) 0.41556(13) 0.0902(5) Uani d . 1 . .
O O3 0.4022(2) 0.65556(18) 0.32038(9) 0.0639(4) Uani d . 1 . .
O O4 0.3900(2) 0.2749(2) -0.00437(8) 0.0597(4) Uani d . 1 . .
H H4 0.3625 0.2787 0.0457 0.089 Uiso calc R 1 . .
O O5 0.81043(17) 0.27761(18) 0.30757(8) 0.0522(3) Uani d . 1 . .
H H5 0.7158 0.2968 0.2867 0.078 Uiso calc R 1 . .
N N1 0.13992(19) 0.27191(19) 0.20210(8) 0.0396(3) Uani d D 1 . .
N N2 0.1602(2) 0.27247(19) 0.11548(8) 0.0403(3) Uani d . 1 . .
N N3 0.2967(2) 0.61957(19) 0.37848(10) 0.0495(4) Uani d . 1 . .
C C1 0.2777(2) 0.2991(2) 0.34961(9) 0.0336(3) Uani d . 1 . .
C C2 0.2633(2) 0.4482(2) 0.40702(9) 0.0363(3) Uani d . 1 . .
C C3 0.2296(2) 0.4472(2) 0.49259(10) 0.0441(4) Uani d . 1 . .
H H3 0.2163 0.5472 0.5288 0.053 Uiso calc R 1 . .
C C4 0.2163(2) 0.2946(2) 0.52303(10) 0.0472(4) Uani d . 1 . .
H H4A 0.1947 0.2917 0.5805 0.057 Uiso calc R 1 . .
C C5 0.2348(2) 0.1460(2) 0.46837(11) 0.0450(4) Uani d . 1 . .
H H5A 0.2286 0.0448 0.4896 0.054 Uiso calc R 1 . .
C C6 0.2625(2) 0.1475(2) 0.38232(10) 0.0386(3) Uani d . 1 . .
H H6 0.2712 0.0453 0.3458 0.046 Uiso calc R 1 . .
C C7 0.3056(2) 0.2892(2) 0.25478(9) 0.0375(3) Uani d . 1 . .
C C8 0.0013(2) 0.2459(2) 0.06163(9) 0.0383(3) Uani d . 1 . .
C C9 -0.2106(3) 0.2077(3) 0.08602(11) 0.0564(5) Uani d . 1 . .
H H9A -0.2363 0.1373 0.1298 0.085 Uiso calc R 1 . .
H H9B -0.3155 0.1361 0.0350 0.085 Uiso calc R 1 . .
H H9C -0.2160 0.3253 0.1089 0.085 Uiso calc R 1 . .
C C10 0.0411(3) 0.2564(2) -0.02863(9) 0.0412(4) Uani d . 1 . .
C C11 0.2322(3) 0.2729(2) -0.05640(10) 0.0468(4) Uani d . 1 . .
C C12 0.2639(4) 0.2882(3) -0.14152(12) 0.0639(5) Uani d . 1 . .
H H12 0.3905 0.3006 -0.1595 0.077 Uiso calc R 1 . .
C C13 0.1107(4) 0.2853(3) -0.19919(12) 0.0712(6) Uani d . 1 . .
H H13 0.1341 0.2953 -0.2558 0.085 Uiso calc R 1 . .
C C14 -0.0770(4) 0.2676(3) -0.17371(12) 0.0678(6) Uani d . 1 . .
H H14 -0.1808 0.2648 -0.2131 0.081 Uiso calc R 1 . .
C C15 -0.1110(3) 0.2540(3) -0.08957(11) 0.0543(4) Uani d . 1 . .
H H15 -0.2382 0.2429 -0.0728 0.065 Uiso calc R 1 . .
C C16 0.7246(3) 0.1002(3) 0.32738(15) 0.0637(5) Uani d . 1 . .
H H16A 0.8322 0.0598 0.3340 0.096 Uiso calc R 1 . .
H H16B 0.6154 0.0097 0.2806 0.096 Uiso calc R 1 . .
H H16C 0.6675 0.1103 0.3810 0.096 Uiso calc R 1 . .
H H1 0.030(2) 0.277(3) 0.2252(11) 0.052(5) 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'
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
C11 O4 H4 . . 109.5 ?
C16 O5 H5 . . 109.5 ?
C7 N1 N2 . . 117.46(12) ?
C7 N1 H1 . . 119.7(12) ?
N2 N1 H1 . . 122.2(12) ?
C8 N2 N1 . . 119.43(12) ?
O2 N3 O3 . . 123.74(15) ?
O2 N3 C2 . . 118.16(15) ?
O3 N3 C2 . . 118.08(14) ?
C6 C1 C2 . . 117.14(13) ?
C6 C1 C7 . . 117.87(13) ?
C2 C1 C7 . . 124.98(13) ?
C3 C2 C1 . . 122.71(14) ?
C3 C2 N3 . . 117.65(14) ?
C1 C2 N3 . . 119.55(13) ?
C4 C3 C2 . . 118.57(15) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 120.24(14) ?
C3 C4 H4A . . 119.9 ?
C5 C4 H4A . . 119.9 ?
C6 C5 C4 . . 120.21(14) ?
C6 C5 H5A . . 119.9 ?
C4 C5 H5A . . 119.9 ?
C5 C6 C1 . . 121.08(14) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
O1 C7 N1 . . 123.95(14) ?
O1 C7 C1 . . 121.23(13) ?
N1 C7 C1 . . 114.72(12) ?
N2 C8 C10 . . 115.28(13) ?
N2 C8 C9 . . 124.13(14) ?
C10 C8 C9 . . 120.59(13) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C15 C10 C11 . . 117.60(15) ?
C15 C10 C8 . . 120.27(15) ?
C11 C10 C8 . . 122.11(14) ?
O4 C11 C12 . . 116.92(16) ?
O4 C11 C10 . . 123.35(14) ?
C12 C11 C10 . . 119.73(16) ?
C13 C12 C11 . . 120.8(2) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 120.37(18) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C13 C14 C15 . . 119.77(18) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C14 C15 C10 . . 121.72(19) ?
C14 C15 H15 . . 119.1 ?
C10 C15 H15 . . 119.1 ?
O5 C16 H16A . . 109.5 ?
O5 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O5 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
O1 C7 . 1.2218(18) ?
O2 N3 . 1.2172(19) ?
O3 N3 . 1.2192(19) ?
O4 C11 . 1.349(2) ?
O4 H4 . 0.82 ?
O5 C16 . 1.410(2) ?
O5 H5 . 0.82 ?
N1 C7 . 1.3472(18) ?
N1 N2 . 1.3812(17) ?
N1 H1 . 0.893(9) ?
N2 C8 . 1.2916(19) ?
N3 C2 . 1.4705(19) ?
C1 C6 . 1.389(2) ?
C1 C2 . 1.392(2) ?
C1 C7 . 1.5083(19) ?
C2 C3 . 1.383(2) ?
C3 C4 . 1.380(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.384(2) ?
C4 H4A . 0.93 ?
C5 C6 . 1.383(2) ?
C5 H5A . 0.93 ?
C6 H6 . 0.93 ?
C8 C10 . 1.478(2) ?
C8 C9 . 1.497(2) ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
C10 C15 . 1.401(2) ?
C10 C11 . 1.412(2) ?
C11 C12 . 1.394(2) ?
C12 C13 . 1.373(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.374(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.379(3) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 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
N1 H1 O5 1_455 0.893(9) 2.080(10) 2.9563(17) 165(2)
O5 H5 O1 . 0.82 1.94 2.7451(16) 168
O4 H4 N2 . 0.82 1.85 2.5612(17) 144
