#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225947.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_2225947
loop_
_publ_author_name
'Han, You-Yue'
'Li, Yong-Hong'
'Zhao, Qiu-Rong'
_publ_section_title
;
 N'-(2,5-Dihydroxybenzylidene)-2-hydroxy-3-methylbenzohydrazide
;
_journal_coeditor_code           OM2333
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1091
_journal_paper_doi               10.1107/S1600536810013395
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H14 N2 O4'
_chemical_formula_moiety         'C15 H14 N2 O4'
_chemical_formula_sum            'C15 H14 N2 O4'
_chemical_formula_weight         286.28
_chemical_name_systematic
;
N'-(2,5-Dihydroxybenzylidene)-2-hydroxy-3-methylbenzohydrazide
;
_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                 94.742(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.333(2)
_cell_length_b                   7.3160(10)
_cell_length_c                   13.738(2)
_cell_measurement_reflns_used    1316
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.7
_cell_volume                     1335.5(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 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART 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  0.0865
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7636
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.823
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0519
_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)+(0.0615P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                1457
_reflns_number_total             3002
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2333.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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225947
_cod_database_fobs_code          2225947
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 0.25674(12) 0.4205(2) 0.31421(10) 0.0660(5) Uani d . 1 . .
H H1 0.2036 0.3785 0.2893 0.099 Uiso calc R 1 . .
O O2 0.12591(10) 0.3298(2) 0.17731(10) 0.0530(4) Uani d . 1 . .
O O3 -0.10549(10) 0.1488(2) 0.03610(9) 0.0528(4) Uani d . 1 . .
H H3 -0.0498 0.1958 0.0467 0.079 Uiso calc R 1 . .
O O4 -0.22237(11) 0.1219(2) -0.35891(9) 0.0555(4) Uani d . 1 . .
H H4 -0.1937 0.2007 -0.3888 0.083 Uiso calc R 1 . .
N N1 0.15386(12) 0.3685(2) 0.01891(11) 0.0451(4) Uani d D 1 . .
H H1A 0.1913(15) 0.405(3) -0.0290(12) 0.080 Uiso d D 1 . .
N N2 0.06052(11) 0.2950(2) -0.00814(11) 0.0441(4) Uani d . 1 . .
C C1 0.28436(13) 0.4534(3) 0.14397(13) 0.0401(5) Uani d . 1 . .
C C2 0.31477(14) 0.4737(3) 0.24325(14) 0.0447(5) Uani d . 1 . .
C C3 0.40822(15) 0.5532(3) 0.27436(15) 0.0513(6) Uani d . 1 . .
C C4 0.46896(16) 0.6081(3) 0.20408(17) 0.0573(6) Uani d . 1 . .
H H4A 0.5310 0.6606 0.2235 0.069 Uiso calc R 1 . .
C C5 0.44147(15) 0.5884(3) 0.10597(16) 0.0570(6) Uani d . 1 . .
H H5 0.4846 0.6271 0.0602 0.068 Uiso calc R 1 . .
C C6 0.34987(14) 0.5113(3) 0.07559(14) 0.0496(5) Uani d . 1 . .
H H6 0.3315 0.4976 0.0092 0.060 Uiso calc R 1 . .
C C7 0.43835(18) 0.5770(4) 0.38160(16) 0.0771(8) Uani d . 1 . .
H H7A 0.5062 0.6219 0.3903 0.116 Uiso calc R 1 . .
H H7B 0.4342 0.4615 0.4142 0.116 Uiso calc R 1 . .
H H7C 0.3939 0.6628 0.4088 0.116 Uiso calc R 1 . .
C C8 0.18276(14) 0.3793(3) 0.11571(14) 0.0412(5) Uani d . 1 . .
C C9 0.03111(14) 0.2882(3) -0.09837(14) 0.0436(5) Uani d . 1 . .
H H9 0.0720 0.3335 -0.1444 0.052 Uiso calc R 1 . .
C C10 -0.06605(13) 0.2097(3) -0.12963(13) 0.0385(5) Uani d . 1 . .
C C11 -0.13067(14) 0.1425(3) -0.06259(13) 0.0404(5) Uani d . 1 . .
C C12 -0.22281(14) 0.0702(3) -0.09566(15) 0.0470(5) Uani d . 1 . .
H H12 -0.2653 0.0246 -0.0511 0.056 Uiso calc R 1 . .
C C13 -0.25242(14) 0.0648(3) -0.19390(14) 0.0462(5) Uani d . 1 . .
H H13 -0.3150 0.0168 -0.2152 0.055 Uiso calc R 1 . .
C C14 -0.18970(14) 0.1304(3) -0.26101(13) 0.0413(5) Uani d . 1 . .
C C15 -0.09706(13) 0.2005(3) -0.22897(13) 0.0418(5) Uani d . 1 . .
H H15 -0.0544 0.2425 -0.2743 0.050 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 ?
C11 O3 H3 . . 109.5 ?
C14 O4 H4 . . 109.5 ?
C8 N1 N2 . . 117.67(16) ?
C8 N1 H1A . . 124.8(15) ?
N2 N1 H1A . . 117.5(15) ?
C9 N2 N1 . . 118.55(16) ?
C2 C1 C6 . . 118.40(17) ?
C2 C1 C8 . . 118.67(18) ?
C6 C1 C8 . . 122.87(17) ?
O1 C2 C1 . . 122.42(18) ?
O1 C2 C3 . . 116.41(18) ?
C1 C2 C3 . . 121.17(19) ?
C4 C3 C2 . . 117.80(18) ?
C4 C3 C7 . . 122.02(19) ?
C2 C3 C7 . . 120.2(2) ?
C3 C4 C5 . . 122.33(19) ?
C3 C4 H4A . . 118.8 ?
C5 C4 H4A . . 118.8 ?
C4 C5 C6 . . 119.8(2) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C6 C1 . . 120.46(19) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
C3 C7 H7A . . 109.5 ?
C3 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C3 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O2 C8 N1 . . 120.92(18) ?
O2 C8 C1 . . 121.82(17) ?
N1 C8 C1 . . 117.26(18) ?
N2 C9 C10 . . 120.09(18) ?
N2 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C15 C10 C11 . . 118.53(17) ?
C15 C10 C9 . . 119.64(18) ?
C11 C10 C9 . . 121.83(17) ?
O3 C11 C12 . . 118.53(18) ?
O3 C11 C10 . . 121.64(17) ?
C12 C11 C10 . . 119.82(17) ?
C13 C12 C11 . . 120.65(19) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C14 . . 120.31(17) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C15 C14 O4 . . 122.08(18) ?
C15 C14 C13 . . 119.55(17) ?
O4 C14 C13 . . 118.36(16) ?
C14 C15 C10 . . 121.11(18) ?
C14 C15 H15 . . 119.4 ?
C10 C15 H15 . . 119.4 ?
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 . 1.351(2) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.236(2) ?
O3 C11 . 1.370(2) ?
O3 H3 . 0.8200 ?
O4 C14 . 1.380(2) ?
O4 H4 . 0.8200 ?
N1 C8 . 1.356(2) ?
N1 N2 . 1.378(2) ?
N1 H1A . 0.899(19) ?
N2 C9 . 1.270(2) ?
C1 C2 . 1.398(2) ?
C1 C6 . 1.400(3) ?
C1 C8 . 1.481(3) ?
C2 C3 . 1.409(3) ?
C3 C4 . 1.371(3) ?
C3 C7 . 1.505(3) ?
C4 C5 . 1.375(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.378(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C9 C10 . 1.449(3) ?
C9 H9 . 0.9300 ?
C10 C15 . 1.395(2) ?
C10 C11 . 1.401(3) ?
C11 C12 . 1.379(3) ?
C12 C13 . 1.375(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.381(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.376(2) ?
C15 H15 . 0.9300 ?
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 O2 . 0.82 1.82 2.5452(19) 147.0
O3 H3 N2 . 0.82 1.85 2.576(2) 146.0
O4 H4 O3 4_565 0.82 1.97 2.774(2) 168.6
N1 H1A O4 2_554 0.899(19) 2.272(15) 3.072(2) 148(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744881
