#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/55/2225514.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_2225514
loop_
_publ_author_name
'Wei, Jing-Yuan'
'Song, De-Guang'
'Wang, Da-Cheng'
'Deng, Xu-Ming'
'Liu, Ju-Xiong'
'Liu, Bo'
_publ_section_title
;
 (E)-N'-(2,5-Dimethoxybenzylidene)-2,4-dihydroxybenzohydrazide
;
_journal_coeditor_code           HB5375
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o996
_journal_paper_doi               10.1107/S160053681001130X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H16 N2 O5'
_chemical_formula_moiety         'C16 H16 N2 O5'
_chemical_formula_sum            'C16 H16 N2 O5'
_chemical_formula_weight         316.31
_chemical_name_systematic
;
(E)-N'-(2,5-Dimethoxybenzylidene)-2,4-dihydroxybenzohydrazide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.80(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8600(16)
_cell_length_b                   15.358(3)
_cell_length_c                   12.425(3)
_cell_measurement_reflns_used    1224
_cell_measurement_temperature    295
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      2.65
_cell_volume                     1478.0(6)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and 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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7757
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.2321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                1698
_reflns_number_total             2626
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5375.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 
;
_cod_original_cell_volume        1478.0(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225514
_cod_database_fobs_code          2225514
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_disorder_assembly
_atom_site_disorder_group
O O1 0.5668(2) 0.18995(10) 0.34476(11) 0.0523(5) Uani d . 1 . .
H H1 0.6007 0.2404 0.3438 0.078 Uiso calc R 1 . .
O O2 0.2931(2) -0.02763(10) 0.10807(13) 0.0623(5) Uani d . 1 . .
H H2 0.3162 -0.0573 0.1635 0.093 Uiso calc R 1 . .
O O3 0.6343(2) 0.33256(9) 0.26549(11) 0.0477(4) Uani d . 1 . .
O O4 0.7730(2) 0.58885(10) -0.13674(12) 0.0569(5) Uani d . 1 . .
O O5 1.0792(2) 0.67891(10) 0.28127(12) 0.0529(4) Uani d . 1 . .
N N1 0.6247(2) 0.35121(10) 0.08522(13) 0.0390(5) Uani d . 1 . .
H H1A 0.5957 0.3331 0.0192 0.047 Uiso calc R 1 . .
N N2 0.7069(2) 0.42982(11) 0.10809(13) 0.0390(5) Uani d . 1 . .
C C1 0.5091(3) 0.21858(13) 0.15178(15) 0.0329(5) Uani d . 1 . .
C C2 0.5058(3) 0.16342(13) 0.24143(16) 0.0354(5) Uani d . 1 . .
C C3 0.4396(3) 0.08035(14) 0.22852(16) 0.0391(5) Uani d . 1 . .
H H3 0.4436 0.0439 0.2887 0.047 Uiso calc R 1 . .
C C4 0.3674(3) 0.05154(14) 0.12604(17) 0.0421(6) Uani d . 1 . .
C C5 0.3657(3) 0.10522(15) 0.03614(17) 0.0527(7) Uani d . 1 . .
H H5 0.3168 0.0857 -0.0331 0.063 Uiso calc R 1 . .
C C6 0.4356(3) 0.18663(14) 0.04918(16) 0.0451(6) Uani d . 1 . .
H H6 0.4342 0.2218 -0.0119 0.054 Uiso calc R 1 . .
C C7 0.5915(3) 0.30376(13) 0.17057(16) 0.0368(5) Uani d . 1 . .
C C8 0.7456(3) 0.47279(13) 0.02779(17) 0.0386(5) Uani d . 1 . .
H H8 0.7160 0.4520 -0.0432 0.046 Uiso calc R 1 . .
C C9 0.8368(3) 0.55503(13) 0.04948(16) 0.0365(5) Uani d . 1 . .
C C10 0.8507(3) 0.61312(14) -0.03424(16) 0.0405(5) Uani d . 1 . .
C C11 0.9361(3) 0.69144(14) -0.01112(19) 0.0463(6) Uani d . 1 . .
H H11 0.9448 0.7304 -0.0672 0.056 Uiso calc R 1 . .
C C12 1.0081(3) 0.71168(15) 0.09455(18) 0.0468(6) Uani d . 1 . .
H H12 1.0627 0.7651 0.1097 0.056 Uiso calc R 1 . .
C C13 1.0003(3) 0.65342(14) 0.17882(17) 0.0405(5) Uani d . 1 . .
C C14 0.9151(3) 0.57596(14) 0.15574(17) 0.0380(5) Uani d . 1 . .
H H14 0.9094 0.5366 0.2119 0.046 Uiso calc R 1 . .
C C15 1.1064(3) 0.61377(16) 0.36363(18) 0.0576(7) Uani d . 1 . .
H H15A 0.9970 0.5938 0.3785 0.086 Uiso calc R 1 . .
H H15B 1.1726 0.6377 0.4290 0.086 Uiso calc R 1 . .
H H15C 1.1680 0.5658 0.3390 0.086 Uiso calc R 1 . .
C C16 0.8212(4) 0.63418(17) -0.22690(18) 0.0649(8) Uani d . 1 . .
H H16A 0.7839 0.6936 -0.2260 0.097 Uiso calc R 1 . .
H H16B 0.7679 0.6070 -0.2938 0.097 Uiso calc R 1 . .
H H16C 0.9445 0.6324 -0.2216 0.097 Uiso calc R 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
C2 O1 H1 . . 109.5 ?
C4 O2 H2 . . 109.5 ?
C10 O4 C16 . . 117.56(18) ?
C13 O5 C15 . . 117.08(17) ?
C7 N1 N2 . . 117.31(17) ?
C7 N1 H1A . . 121.3 ?
N2 N1 H1A . . 121.3 ?
C8 N2 N1 . . 117.29(17) ?
C6 C1 C2 . . 116.88(19) ?
C6 C1 C7 . . 124.33(18) ?
C2 C1 C7 . . 118.77(18) ?
O1 C2 C3 . . 117.07(18) ?
O1 C2 C1 . . 121.30(19) ?
C3 C2 C1 . . 121.64(19) ?
C4 C3 C2 . . 119.61(19) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
O2 C4 C3 . . 122.76(19) ?
O2 C4 C5 . . 117.22(19) ?
C3 C4 C5 . . 120.0(2) ?
C6 C5 C4 . . 120.1(2) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C1 . . 121.75(19) ?
C5 C6 H6 . . 119.1 ?
C1 C6 H6 . . 119.1 ?
O3 C7 N1 . . 119.56(19) ?
O3 C7 C1 . . 120.54(18) ?
N1 C7 C1 . . 119.89(18) ?
N2 C8 C9 . . 118.67(19) ?
N2 C8 H8 . . 120.7 ?
C9 C8 H8 . . 120.7 ?
C10 C9 C14 . . 118.8(2) ?
C10 C9 C8 . . 121.21(19) ?
C14 C9 C8 . . 119.95(19) ?
O4 C10 C11 . . 123.68(19) ?
O4 C10 C9 . . 116.29(19) ?
C11 C10 C9 . . 120.0(2) ?
C12 C11 C10 . . 120.1(2) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 120.8(2) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C14 C13 O5 . . 124.6(2) ?
C14 C13 C12 . . 119.0(2) ?
O5 C13 C12 . . 116.4(2) ?
C13 C14 C9 . . 121.2(2) ?
C13 C14 H14 . . 119.4 ?
C9 C14 H14 . . 119.4 ?
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 ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 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 C2 . 1.355(2) ?
O1 H1 . 0.8200 ?
O2 C4 . 1.351(2) ?
O2 H2 . 0.8200 ?
O3 C7 . 1.251(2) ?
O4 C10 . 1.367(2) ?
O4 C16 . 1.424(3) ?
O5 C13 . 1.375(2) ?
O5 C15 . 1.421(3) ?
N1 C7 . 1.348(2) ?
N1 N2 . 1.376(2) ?
N1 H1A . 0.8600 ?
N2 C8 . 1.275(2) ?
C1 C6 . 1.396(3) ?
C1 C2 . 1.403(3) ?
C1 C7 . 1.461(3) ?
C2 C3 . 1.377(3) ?
C3 C4 . 1.376(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.387(3) ?
C5 C6 . 1.364(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 C9 . 1.455(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.389(3) ?
C9 C14 . 1.396(3) ?
C10 C11 . 1.384(3) ?
C11 C12 . 1.374(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.387(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.371(3) ?
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
O1 H1 O3 . 0.82 1.76 2.495(2) 148
O2 H2 O3 2_645 0.82 1.92 2.664(2) 151
N1 H1A O1 4_565 0.86 2.17 3.012(2) 166
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C8 . . . . 176.80(19) ?
C6 C1 C2 O1 . . . . -176.99(19) ?
C7 C1 C2 O1 . . . . 4.5(3) ?
C6 C1 C2 C3 . . . . 2.6(3) ?
C7 C1 C2 C3 . . . . -175.98(19) ?
O1 C2 C3 C4 . . . . 176.54(19) ?
C1 C2 C3 C4 . . . . -3.0(3) ?
C2 C3 C4 O2 . . . . -176.9(2) ?
C2 C3 C4 C5 . . . . 1.7(3) ?
O2 C4 C5 C6 . . . . 178.7(2) ?
C3 C4 C5 C6 . . . . 0.0(4) ?
C4 C5 C6 C1 . . . . -0.4(4) ?
C2 C1 C6 C5 . . . . -0.8(3) ?
C7 C1 C6 C5 . . . . 177.6(2) ?
N2 N1 C7 O3 . . . . 0.6(3) ?
N2 N1 C7 C1 . . . . -178.22(17) ?
C6 C1 C7 O3 . . . . 170.6(2) ?
C2 C1 C7 O3 . . . . -11.0(3) ?
C6 C1 C7 N1 . . . . -10.6(3) ?
C2 C1 C7 N1 . . . . 167.86(19) ?
N1 N2 C8 C9 . . . . -178.34(17) ?
N2 C8 C9 C10 . . . . -166.4(2) ?
N2 C8 C9 C14 . . . . 14.8(3) ?
C16 O4 C10 C11 . . . . 17.6(3) ?
C16 O4 C10 C9 . . . . -163.9(2) ?
C14 C9 C10 O4 . . . . 179.36(18) ?
C8 C9 C10 O4 . . . . 0.6(3) ?
C14 C9 C10 C11 . . . . -2.1(3) ?
C8 C9 C10 C11 . . . . 179.09(19) ?
O4 C10 C11 C12 . . . . 178.8(2) ?
C9 C10 C11 C12 . . . . 0.4(3) ?
C10 C11 C12 C13 . . . . 1.7(3) ?
C15 O5 C13 C14 . . . . 14.2(3) ?
C15 O5 C13 C12 . . . . -166.4(2) ?
C11 C12 C13 C14 . . . . -1.9(3) ?
C11 C12 C13 O5 . . . . 178.70(19) ?
O5 C13 C14 C9 . . . . 179.43(19) ?
C12 C13 C14 C9 . . . . 0.0(3) ?
C10 C9 C14 C13 . . . . 1.9(3) ?
C8 C9 C14 C13 . . . . -179.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744775
