#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/64/2226497.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_2226497
loop_
_publ_author_name
'Hang, Zhi-Xi'
'Dong, Bo'
'Wang, Xing-Wen'
_publ_section_title
;
 2-[(2-Hydroxy-4-methoxybenzylidene)azaniumyl]benzoate monohydrate
;
_journal_coeditor_code           HB5506
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1776
_journal_paper_doi               10.1107/S1600536810023949
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 N O4, H2 O'
_chemical_formula_moiety         'C15 H13 N O4, H2 O'
_chemical_formula_sum            'C15 H15 N O5'
_chemical_formula_weight         289.28
_chemical_name_systematic
;
2-[(2-Hydroxy-4-methoxybenzylidene)azaniumyl]benzoate monohydrate
;
_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                111.312(2)
_cell_angle_beta                 93.084(3)
_cell_angle_gamma                117.500(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7240(5)
_cell_length_b                   8.9252(4)
_cell_length_c                   10.7967(5)
_cell_measurement_reflns_used    1109
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.2
_cell_measurement_theta_min      2.6
_cell_volume                     669.24(6)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0131
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4045
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0431
_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)+(0.0595P)²+0.0161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1218
_reflns_number_gt                1992
_reflns_number_total             2810
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5506.cif
_cod_data_source_block           I
_cod_database_code               2226497
_cod_database_fobs_code          2226497
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
N N1 0.91763(18) 0.38037(19) 0.21508(14) 0.0364(3) Uani d D 1 . .
O O1 0.65275(15) 0.22394(15) -0.01717(12) 0.0446(3) Uani d D 1 . .
O O2 0.65944(15) 0.04540(16) 0.17602(12) 0.0491(3) Uani d . 1 . .
O O3 0.65792(17) -0.01967(18) 0.35525(13) 0.0611(4) Uani d . 1 . .
O O4 0.59187(15) 0.62901(16) -0.17000(12) 0.0459(3) Uani d . 1 . .
O O5 0.68483(19) 0.0450(2) 0.63223(16) 0.0715(5) Uani d D 1 . .
C C1 0.8648(2) 0.5485(2) 0.10069(16) 0.0356(4) Uani d . 1 . .
C C2 0.7092(2) 0.3956(2) -0.00735(16) 0.0341(4) Uani d . 1 . .
C C3 0.6248(2) 0.4303(2) -0.09650(16) 0.0364(4) Uani d . 1 . .
H H3 0.5244 0.3306 -0.1682 0.044 Uiso calc R 1 . .
C C4 0.6884(2) 0.6120(2) -0.07994(16) 0.0371(4) Uani d . 1 . .
C C5 0.8428(2) 0.7642(2) 0.02468(18) 0.0431(4) Uani d . 1 . .
H H5 0.8866 0.8859 0.0346 0.052 Uiso calc R 1 . .
C C6 0.9272(2) 0.7302(2) 0.11142(18) 0.0430(4) Uani d . 1 . .
H H6 1.0301 0.8309 0.1805 0.052 Uiso calc R 1 . .
C C7 0.9597(2) 0.5313(2) 0.19950(17) 0.0377(4) Uani d . 1 . .
H H7 1.0645 0.6404 0.2605 0.045 Uiso calc R 1 . .
C C8 1.0163(2) 0.3714(2) 0.31829(16) 0.0371(4) Uani d . 1 . .
C C9 0.9308(2) 0.2225(2) 0.35416(16) 0.0381(4) Uani d . 1 . .
C C10 1.0311(2) 0.2180(3) 0.45585(19) 0.0486(5) Uani d . 1 . .
H H10 0.9764 0.1205 0.4813 0.058 Uiso calc R 1 . .
C C11 1.2094(3) 0.3539(3) 0.5200(2) 0.0542(5) Uani d . 1 . .
H H11 1.2743 0.3465 0.5865 0.065 Uiso calc R 1 . .
C C12 1.2902(2) 0.5003(3) 0.48467(19) 0.0520(5) Uani d . 1 . .
H H12 1.4098 0.5937 0.5289 0.062 Uiso calc R 1 . .
C C13 1.1959(2) 0.5100(2) 0.38442(18) 0.0449(4) Uani d . 1 . .
H H13 1.2520 0.6092 0.3608 0.054 Uiso calc R 1 . .
C C14 0.7341(2) 0.0706(2) 0.29112(17) 0.0408(4) Uani d . 1 . .
C C15 0.6600(3) 0.8098(3) -0.1699(2) 0.0545(5) Uani d . 1 . .
H H15A 0.6832 0.9017 -0.0787 0.082 Uiso calc R 1 . .
H H15B 0.5730 0.8035 -0.2330 0.082 Uiso calc R 1 . .
H H15C 0.7693 0.8447 -0.1978 0.082 Uiso calc R 1 . .
H H5B 0.675(3) 0.022(3) 0.5468(12) 0.080 Uiso d D 1 . .
H H5A 0.591(2) 0.046(3) 0.648(2) 0.080 Uiso d D 1 . .
H H1 0.8112(18) 0.2707(19) 0.166(2) 0.080 Uiso d D 1 . .
H H1A 0.5504(18) 0.145(3) -0.0780(19) 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
C7 N1 C8 . . 125.26(14) ?
C7 N1 H1 . . 121.8(13) ?
C8 N1 H1 . . 112.5(13) ?
C2 O1 H1A . . 109.4(15) ?
C4 O4 C15 . . 118.67(13) ?
H5B O5 H5A . . 105.0(17) ?
C6 C1 C7 . . 117.43(14) ?
C6 C1 C2 . . 117.96(14) ?
C7 C1 C2 . . 124.60(14) ?
O1 C2 C3 . . 123.29(14) ?
O1 C2 C1 . . 117.29(14) ?
C3 C2 C1 . . 119.42(14) ?
C2 C3 C4 . . 120.63(14) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
O4 C4 C3 . . 115.29(14) ?
O4 C4 C5 . . 123.87(14) ?
C3 C4 C5 . . 120.83(14) ?
C6 C5 C4 . . 118.62(15) ?
C6 C5 H5 . . 120.7 ?
C4 C5 H5 . . 120.7 ?
C5 C6 C1 . . 122.51(15) ?
C5 C6 H6 . . 118.7 ?
C1 C6 H6 . . 118.7 ?
N1 C7 C1 . . 127.47(15) ?
N1 C7 H7 . . 116.3 ?
C1 C7 H7 . . 116.3 ?
C13 C8 C9 . . 120.22(15) ?
C13 C8 N1 . . 120.48(15) ?
C9 C8 N1 . . 119.29(14) ?
C10 C9 C8 . . 117.87(16) ?
C10 C9 C14 . . 118.71(16) ?
C8 C9 C14 . . 123.39(15) ?
C11 C10 C9 . . 121.89(18) ?
C11 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
C12 C11 C10 . . 119.34(17) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C13 . . 120.63(17) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C12 C13 C8 . . 120.03(17) ?
C12 C13 H13 . . 120.0 ?
C8 C13 H13 . . 120.0 ?
O3 C14 O2 . . 124.52(16) ?
O3 C14 C9 . . 118.27(15) ?
O2 C14 C9 . . 117.21(15) ?
O4 C15 H15A . . 109.5 ?
O4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O4 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
N1 C7 . 1.301(2) ?
N1 C8 . 1.420(2) ?
N1 H1 . 0.912(9) ?
O1 C2 . 1.3346(18) ?
O1 H1A . 0.863(10) ?
O2 C14 . 1.2625(19) ?
O3 C14 . 1.237(2) ?
O4 C4 . 1.3474(18) ?
O4 C15 . 1.438(2) ?
O5 H5B . 0.858(9) ?
O5 H5A . 0.851(9) ?
C1 C6 . 1.408(2) ?
C1 C7 . 1.410(2) ?
C1 C2 . 1.424(2) ?
C2 C3 . 1.384(2) ?
C3 C4 . 1.384(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.403(2) ?
C5 C6 . 1.360(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C13 . 1.393(2) ?
C8 C9 . 1.400(2) ?
C9 C10 . 1.391(2) ?
C9 C14 . 1.517(2) ?
C10 C11 . 1.379(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.375(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.377(2) ?
C12 H12 . 0.9300 ?
C13 H13 . 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
N1 H1 O1 . 0.912(9) 2.137(19) 2.7257(17) 121.4(17)
N1 H1 O2 . 0.912(9) 1.877(16) 2.6366(17) 139.3(19)
O1 H1A O2 2_655 0.863(10) 1.724(11) 2.5675(16) 165(2)
O5 H5A O3 2_656 0.851(9) 2.068(11) 2.907(2) 169(2)
O5 H5B O3 . 0.858(9) 1.948(9) 2.806(2) 178(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656122
