#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/59/2225991.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_2225991
loop_
_publ_author_name
'Han, You-Yue'
'Li, Yong-Hong'
'Zhao, Qiu-Rong'
_publ_section_title
;
 (E)-2,4-Dihydroxy-N'-(2-hydroxy-3-methoxy-5-nitrobenzylidene)benzohydrazide
 dihydrate
;
_journal_coeditor_code           SU2173
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1085
_journal_page_last               o1086
_journal_paper_doi               10.1107/S1600536810013000
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 N3 O7 , 2H2 O'
_chemical_formula_moiety         'C15 H13 N3 O7 , 2H2 O'
_chemical_formula_sum            'C15 H17 N3 O9'
_chemical_formula_weight         383.32
_chemical_name_systematic
;
(E)-2,4-Dihydroxy-N'-(2-hydroxy-3-methoxy-5-
nitrobenzylidene)benzohydrazide dihydrate
;
_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           SHELXL97
_cell_angle_alpha                95.43(2)
_cell_angle_beta                 96.21(2)
_cell_angle_gamma                102.01(2)
_cell_formula_units_Z            2
_cell_length_a                   7.976(2)
_cell_length_b                   9.325(2)
_cell_length_c                   11.547(3)
_cell_measurement_reflns_used    1898
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      2.6
_cell_volume                     829.0(4)
_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  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11747
_diffrn_reflns_theta_full        29.24
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4268
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.0500
_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)+(0.0611P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1431
_reflns_number_gt                1790
_reflns_number_total             4268
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2173.cif
_cod_data_source_block           I
_cod_database_code               2225991
_cod_database_fobs_code          2225991
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 0.8600(2) 0.84330(17) 1.02241(12) 0.0573(5) Uani d . 1 . .
H H1 0.8627 0.7814 1.0681 0.086 Uiso calc R 1 . .
O O2 0.6371(2) 0.89359(17) 0.64100(13) 0.0605(5) Uani d . 1 . .
H H2 0.5636 0.8519 0.5863 0.091 Uiso calc R 1 . .
O O3 0.4100(2) 0.68584(17) 0.52377(12) 0.0534(4) Uani d . 1 . .
O O4 0.0820(2) 0.45944(17) 0.28656(12) 0.0534(4) Uani d . 1 . .
H H4 0.1460 0.4812 0.3491 0.080 Uiso calc R 1 . .
O O5 -0.3563(2) -0.1600(2) 0.34555(17) 0.0764(6) Uani d . 1 . .
O O6 -0.4541(2) -0.1357(2) 0.16969(16) 0.0838(6) Uani d . 1 . .
O O7 -0.1224(2) 0.36004(18) 0.09529(12) 0.0555(5) Uani d . 1 . .
O O8 0.8842(2) 0.6698(2) 0.19713(15) 0.0631(5) Uani d D 1 . .
O O9 0.8089(2) 0.1954(2) 0.65935(17) 0.0796(6) Uani d D 1 . .
N N1 0.3056(2) 0.4776(2) 0.59954(14) 0.0453(5) Uani d D 1 . .
N N2 0.1982(2) 0.4267(2) 0.49649(14) 0.0441(5) Uani d . 1 . .
N N3 -0.3569(3) -0.0901(2) 0.26028(19) 0.0568(6) Uani d . 1 . .
C C1 0.5283(3) 0.6659(2) 0.71728(17) 0.0384(5) Uani d . 1 . .
C C2 0.6353(3) 0.8076(2) 0.72930(18) 0.0423(6) Uani d . 1 . .
C C3 0.7446(3) 0.8642(3) 0.83179(19) 0.0472(6) Uani d . 1 . .
H H3 0.8159 0.9579 0.8379 0.057 Uiso calc R 1 . .
C C4 0.7485(3) 0.7825(3) 0.92498(17) 0.0427(6) Uani d . 1 . .
C C5 0.6437(3) 0.6424(3) 0.91557(18) 0.0466(6) Uani d . 1 . .
H H5 0.6457 0.5871 0.9784 0.056 Uiso calc R 1 . .
C C6 0.5371(3) 0.5857(2) 0.81357(18) 0.0455(6) Uani d . 1 . .
H H6 0.4684 0.4909 0.8079 0.055 Uiso calc R 1 . .
C C7 0.4131(3) 0.6119(2) 0.60768(17) 0.0390(5) Uani d . 1 . .
C C8 0.0968(3) 0.3000(3) 0.48753(18) 0.0464(6) Uani d . 1 . .
H H8 0.0971 0.2439 0.5500 0.056 Uiso calc R 1 . .
C C9 -0.0187(3) 0.2433(2) 0.38010(17) 0.0417(5) Uani d . 1 . .
C C10 -0.0196(3) 0.3255(2) 0.28470(18) 0.0419(5) Uani d . 1 . .
C C11 -0.1331(3) 0.2684(3) 0.18101(18) 0.0443(6) Uani d . 1 . .
C C12 -0.2421(3) 0.1325(3) 0.17254(19) 0.0481(6) Uani d . 1 . .
H H12 -0.3166 0.0939 0.1040 0.058 Uiso calc R 1 . .
C C13 -0.2392(3) 0.0535(3) 0.26850(19) 0.0471(6) Uani d . 1 . .
C C14 -0.1305(3) 0.1057(3) 0.37055(18) 0.0475(6) Uani d . 1 . .
H H14 -0.1315 0.0496 0.4330 0.057 Uiso calc R 1 . .
C C15 -0.2229(3) 0.3030(3) -0.01694(19) 0.0638(7) Uani d . 1 . .
H H15A -0.1958 0.2112 -0.0447 0.096 Uiso calc R 1 . .
H H15B -0.1962 0.3727 -0.0719 0.096 Uiso calc R 1 . .
H H15C -0.3438 0.2869 -0.0090 0.096 Uiso calc R 1 . .
H H1A 0.296(3) 0.418(2) 0.6542(17) 0.080 Uiso d D 1 . .
H H8A 0.977(2) 0.715(2) 0.2410(19) 0.080 Uiso d D 1 . .
H H9A 0.759(3) 0.1042(12) 0.657(2) 0.080 Uiso d D 1 . .
H H9B 0.743(3) 0.234(2) 0.615(2) 0.080 Uiso d D 1 . .
H H8B 0.906(3) 0.5873(17) 0.172(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'
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
C4 O1 H1 . . 109.5 ?
C2 O2 H2 . . 109.5 ?
C10 O4 H4 . . 109.5 ?
C11 O7 C15 . . 117.01(18) ?
H8A O8 H8B . . 104.2(19) ?
H9A O9 H9B . . 106.7(19) ?
C7 N1 N2 . . 117.96(17) ?
C7 N1 H1A . . 127.0(17) ?
N2 N1 H1A . . 115.1(17) ?
C8 N2 N1 . . 118.57(18) ?
O6 N3 O5 . . 122.4(2) ?
O6 N3 C13 . . 118.6(2) ?
O5 N3 C13 . . 118.98(19) ?
C2 C1 C6 . . 117.07(18) ?
C2 C1 C7 . . 118.85(19) ?
C6 C1 C7 . . 124.1(2) ?
O2 C2 C3 . . 117.5(2) ?
O2 C2 C1 . . 121.57(18) ?
C3 C2 C1 . . 120.9(2) ?
C4 C3 C2 . . 120.3(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
O1 C4 C3 . . 117.5(2) ?
O1 C4 C5 . . 122.60(19) ?
C3 C4 C5 . . 119.93(19) ?
C6 C5 C4 . . 119.8(2) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C1 . . 122.0(2) ?
C5 C6 H6 . . 119.0 ?
C1 C6 H6 . . 119.0 ?
O3 C7 N1 . . 119.77(18) ?
O3 C7 C1 . . 122.2(2) ?
N1 C7 C1 . . 118.00(19) ?
N2 C8 C9 . . 120.0(2) ?
N2 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C14 C9 C10 . . 119.15(19) ?
C14 C9 C8 . . 120.0(2) ?
C10 C9 C8 . . 120.8(2) ?
O4 C10 C9 . . 123.22(18) ?
O4 C10 C11 . . 116.9(2) ?
C9 C10 C11 . . 119.9(2) ?
O7 C11 C12 . . 125.54(19) ?
O7 C11 C10 . . 114.1(2) ?
C12 C11 C10 . . 120.4(2) ?
C11 C12 C13 . . 118.6(2) ?
C11 C12 H12 . . 120.7 ?
C13 C12 H12 . . 120.7 ?
C14 C13 C12 . . 122.6(2) ?
C14 C13 N3 . . 118.8(2) ?
C12 C13 N3 . . 118.6(2) ?
C13 C14 C9 . . 119.4(2) ?
C13 C14 H14 . . 120.3 ?
C9 C14 H14 . . 120.3 ?
O7 C15 H15A . . 109.5 ?
O7 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O7 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.353(2) ?
O1 H1 . 0.8200 ?
O2 C2 . 1.355(2) ?
O2 H2 . 0.8200 ?
O3 C7 . 1.242(2) ?
O4 C10 . 1.337(2) ?
O4 H4 . 0.8200 ?
O5 N3 . 1.232(2) ?
O6 N3 . 1.216(2) ?
O7 C11 . 1.366(3) ?
O7 C15 . 1.439(2) ?
O8 H8A . 0.855(19) ?
O8 H8B . 0.855(19) ?
O9 H9A . 0.857(9) ?
O9 H9B . 0.85(2) ?
N1 C7 . 1.352(3) ?
N1 N2 . 1.370(2) ?
N1 H1A . 0.881(10) ?
N2 C8 . 1.274(3) ?
N3 C13 . 1.455(3) ?
C1 C2 . 1.401(3) ?
C1 C6 . 1.402(3) ?
C1 C7 . 1.461(3) ?
C2 C3 . 1.381(3) ?
C3 C4 . 1.377(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.384(3) ?
C5 C6 . 1.367(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 C9 . 1.447(3) ?
C8 H8 . 0.9300 ?
C9 C14 . 1.389(3) ?
C9 C10 . 1.401(3) ?
C10 C11 . 1.407(3) ?
C11 C12 . 1.368(3) ?
C12 C13 . 1.388(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.368(3) ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
O8 H8B O4 1_655 0.855(19) 2.39(2) 2.953(2) 124(2)
O8 H8B O7 1_655 0.855(19) 2.175(11) 3.001(3) 163(2)
O9 H9B O3 2_666 0.85(2) 2.188(11) 3.032(2) 170(3)
O9 H9A O2 1_545 0.857(9) 1.984(10) 2.840(2) 176(2)
O8 H8A O9 2_766 0.855(19) 1.932(10) 2.786(2) 176(2)
N1 H1A O5 2_556 0.881(10) 2.55(2) 3.183(3) 130(2)
N1 H1A O8 2_666 0.881(10) 2.445(18) 3.195(3) 143(2)
O4 H4 N2 . 0.82 1.85 2.569(2) 146
O2 H2 O3 . 0.82 1.80 2.526(2) 147
O1 H1 O8 1_556 0.82 1.91 2.718(2) 169
