#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/22/8102271.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102271
loop_
_publ_author_name
'Shan-Shan Huang'
'Yun-Peng Diao'
'Ting-Guo Kang'
_publ_section_title
;
 Crystal structure of 3,5-dihydroxybenzoic acid
 [1-(2-hydroxy-3-methoxyphenyl)methylidene]hydrazide - methanol - water
 (1:1:1), (C15H14N2O) · CH3OH · H2O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              167
_journal_volume                  223
_journal_year                    2008
_chemical_formula_moiety         'C15 H14 N2 O5, C H4 O, H2 O'
_chemical_formula_sum            'C16 H20 N2 O7'
_chemical_formula_weight         352.34
_space_group_IT_number           2
_symmetry_cell_setting           monoclinic
_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                94.82(3)
_cell_angle_beta                 99.36(3)
_cell_angle_gamma                107.13(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0230(16)
_cell_length_b                   9.7140(19)
_cell_length_c                   11.583(2)
_cell_measurement_reflns_used    2799
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.2
_cell_volume                     842.8(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Siemens P4'
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5334
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9784
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3726
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0457
_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)+(0.0530P)²+0.1847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                2400
_reflns_number_total             3726
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-2241.cff
_cod_data_source_block           diao
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               8102271
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.19359(18) 0.05973(15) 0.96442(12) 0.0380(3) Uani 1 1 d . . .
N2 N 0.10896(18) 0.11486(15) 0.87552(12) 0.0391(3) Uani 1 1 d D . .
O1 O 0.35748(17) 0.07631(13) 1.17996(11) 0.0475(3) Uani 1 1 d . . .
H1 H 0.3005 0.1018 1.1251 0.071 Uiso 1 1 calc R . .
O2 O 0.52744(19) -0.03896(15) 1.33647(11) 0.0575(4) Uani 1 1 d . . .
O3 O 0.14301(18) 0.31601(14) 1.00087(11) 0.0529(4) Uani 1 1 d . . .
O4 O -0.1348(2) 0.24628(16) 0.48265(11) 0.0652(4) Uani 1 1 d . . .
H4 H -0.2074 0.2753 0.4418 0.098 Uiso 1 1 calc R . .
O5 O -0.1406(2) 0.62728(14) 0.76723(11) 0.0569(4) Uani 1 1 d . . .
H5 H -0.1351 0.6437 0.8386 0.085 Uiso 1 1 calc R . .
O6 O 0.0344(3) 0.10216(16) 0.33943(14) 0.0701(5) Uani 1 1 d D . .
O7 O 0.6163(3) 0.30176(17) 0.33900(19) 0.1138(9) Uani 1 1 d . . .
H7 H 0.5410 0.2312 0.2974 0.171 Uiso 1 1 calc R . .
C1 C 0.3137(2) -0.12361(17) 1.02699(15) 0.0364(4) Uani 1 1 d . . .
C2 C 0.3781(2) -0.05350(17) 1.14317(15) 0.0363(4) Uani 1 1 d . . .
C3 C 0.4675(2) -0.11741(19) 1.22644(16) 0.0415(4) Uani 1 1 d . . .
C4 C 0.4894(2) -0.2498(2) 1.19271(18) 0.0472(5) Uani 1 1 d . . .
H4A H 0.5479 -0.2927 1.2479 0.057 Uiso 1 1 calc R . .
C5 C 0.4253(3) -0.3193(2) 1.07793(18) 0.0504(5) Uani 1 1 d . . .
H5A H 0.4402 -0.4087 1.0565 0.060 Uiso 1 1 calc R . .
C6 C 0.3396(2) -0.25681(19) 0.99543(17) 0.0447(4) Uani 1 1 d . . .
H6 H 0.2985 -0.3034 0.9180 0.054 Uiso 1 1 calc R . .
C7 C 0.6129(3) -0.1020(3) 1.42597(18) 0.0644(6) Uani 1 1 d . . .
H7A H 0.5314 -0.1925 1.4367 0.097 Uiso 1 1 calc R . .
H7B H 0.6497 -0.0367 1.4989 0.097 Uiso 1 1 calc R . .
H7C H 0.7152 -0.1193 1.4024 0.097 Uiso 1 1 calc R . .
C8 C 0.2226(2) -0.06085(18) 0.93756(15) 0.0387(4) Uani 1 1 d . . .
H8 H 0.1851 -0.1082 0.8603 0.046 Uiso 1 1 calc R . .
C9 C 0.0919(2) 0.24773(18) 0.90065(14) 0.0373(4) Uani 1 1 d . . .
C10 C 0.0102(2) 0.30916(18) 0.80032(14) 0.0359(4) Uani 1 1 d . . .
C11 C -0.0242(2) 0.43820(18) 0.82930(15) 0.0393(4) Uani 1 1 d . . .
H11 H 0.0041 0.4819 0.9075 0.047 Uiso 1 1 calc R . .
C12 C -0.1006(2) 0.50171(18) 0.74185(15) 0.0409(4) Uani 1 1 d . . .
C13 C -0.1375(2) 0.44027(19) 0.62507(16) 0.0438(4) Uani 1 1 d . . .
H13 H -0.1860 0.4846 0.5661 0.053 Uiso 1 1 calc R . .
C14 C -0.1015(2) 0.31184(19) 0.59643(15) 0.0438(4) Uani 1 1 d . . .
C15 C -0.0286(2) 0.24513(19) 0.68312(15) 0.0419(4) Uani 1 1 d . . .
H15 H -0.0059 0.1585 0.6633 0.050 Uiso 1 1 calc R . .
C16 C 0.5894(3) 0.4267(3) 0.3063(2) 0.0758(7) Uani 1 1 d . . .
H16A H 0.5177 0.4578 0.3552 0.114 Uiso 1 1 calc R . .
H16B H 0.5297 0.4089 0.2251 0.114 Uiso 1 1 calc R . .
H16C H 0.7020 0.5013 0.3157 0.114 Uiso 1 1 calc R . .
H2 H 0.070(3) 0.062(2) 0.8034(12) 0.080 Uiso 1 1 d D . .
H6A H -0.017(3) 0.132(2) 0.3902(17) 0.080 Uiso 1 1 d D . .
H6B H 0.091(3) 0.1776(17) 0.313(2) 0.080 Uiso 1 1 d D . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 N2 117.67(14) . . ?
C9 N2 N1 118.03(14) . . ?
C9 N2 H2 123.5(15) . . ?
N1 N2 H2 118.5(15) . . ?
C2 O1 H1 109.5 . . ?
C3 O2 C7 117.27(16) . . ?
C14 O4 H4 109.5 . . ?
C12 O5 H5 109.5 . . ?
H6A O6 H6B 105.8(17) . . ?
C16 O7 H7 109.5 . . ?
C2 C1 C6 119.35(16) . . ?
C2 C1 C8 121.73(15) . . ?
C6 C1 C8 118.92(16) . . ?
O1 C2 C1 122.44(15) . . ?
O1 C2 C3 117.80(15) . . ?
C1 C2 C3 119.76(15) . . ?
O2 C3 C4 125.53(16) . . ?
O2 C3 C2 115.01(15) . . ?
C4 C3 C2 119.46(16) . . ?
C3 C4 C5 120.78(17) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 120.20(17) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C1 120.43(17) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C1 120.34(16) . . ?
N1 C8 H8 119.8 . . ?
C1 C8 H8 119.8 . . ?
O3 C9 N2 121.73(16) . . ?
O3 C9 C10 121.43(16) . . ?
N2 C9 C10 116.83(14) . . ?
C11 C10 C15 120.13(16) . . ?
C11 C10 C9 116.29(15) . . ?
C15 C10 C9 123.57(15) . . ?
C12 C11 C10 119.95(16) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
O5 C12 C13 117.88(16) . . ?
O5 C12 C11 121.71(16) . . ?
C13 C12 C11 120.41(16) . . ?
C12 C13 C14 119.39(16) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
O4 C14 C15 117.07(16) . . ?
O4 C14 C13 122.00(16) . . ?
C15 C14 C13 120.93(16) . . ?
C14 C15 C10 119.15(16) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.283(2) . ?
N1 N2 1.3739(19) . ?
N2 C9 1.350(2) . ?
N2 H2 0.900(10) . ?
O1 C2 1.3619(19) . ?
O1 H1 0.8200 . ?
O2 C3 1.363(2) . ?
O2 C7 1.430(2) . ?
O3 C9 1.229(2) . ?
O4 C14 1.363(2) . ?
O4 H4 0.8200 . ?
O5 C12 1.371(2) . ?
O5 H5 0.8200 . ?
O6 H6A 0.850(9) . ?
O6 H6B 0.852(9) . ?
O7 C16 1.367(3) . ?
O7 H7 0.8200 . ?
C1 C2 1.398(2) . ?
C1 C6 1.398(2) . ?
C1 C8 1.449(2) . ?
C2 C3 1.403(2) . ?
C3 C4 1.382(3) . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.373(3) . ?
C5 H5A 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C9 C10 1.495(2) . ?
C10 C11 1.387(2) . ?
C10 C15 1.390(2) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(2) . ?
C13 C14 1.387(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(2) . ?
C15 H15 0.9300 . ?
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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6B O5 0.852(9) 2.139(13) 2.954(2) 160(2) 2_566
O6 H6A O4 0.850(9) 2.003(12) 2.831(2) 164(2) .
N2 H2 O6 0.900(10) 2.072(11) 2.954(2) 166(2) 2_556
O7 H7 O1 0.82 2.00 2.811(2) 172 1_554
O5 H5 O3 0.82 1.88 2.7007(19) 175 2_567
O4 H4 O7 0.82 1.79 2.598(2) 169 1_455
O1 H1 N1 0.82 1.87 2.5937(19) 146 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653935
