##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2006-07-30
_journal_date_accepted     2006-08-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      9
_journal_page_first     o3782
_journal_page_last     o3783
_journal_paper_category     EO
_journal_coeditor_code     CV2093
_publ_contact_author_name     'Prof. Zhang Shu-Sheng'
_publ_contact_author_address
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
_publ_contact_author_email     shushzhang@126.com
_publ_contact_author_fax     '+86 532 84022750'
_publ_contact_author_phone     '+86 532 84022750'
_publ_section_title
;
2-Hydroxy-N-(2-pyridylmethyl)benzamide monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Yong-Hong Wen' ?
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
    'Yue-Qin Yu' ?
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
    'Kun Zhang' ?
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
    'Xue-Mei Li' ?
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
    'Shu-Sheng Zhang' ?
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Hydroxy-N-(2-pyridylmethyl)benzamide monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H12 N2 O2, H2 O'
_chemical_formula_sum     'C13 H14 N2 O3'
_chemical_formula_iupac     'C13 H12 N2 O2, H2 O'
_chemical_formula_weight     246.26
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
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'
_cell_length_a     10.849(3)
_cell_length_b     4.6324(13)
_cell_length_c     25.094(6)
_cell_angle_alpha     90.00
_cell_angle_beta     102.484(9)
_cell_angle_gamma     90.00
_cell_volume     1231.3(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     704
_cell_measurement_theta_min     2.8
_cell_measurement_theta_max     21.2
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.328
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9537
_exptl_absorpt_correction_T_max     0.9933
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     6488
_diffrn_reflns_av_R_equivalents     0.0461
_diffrn_reflns_av_sigmaI/netI     0.0599
_diffrn_reflns_theta_min     1.92
_diffrn_reflns_theta_max     26.02
_diffrn_reflns_theta_full     26.02
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2434
_reflns_number_gt     1321
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1103
_refine_ls_R_factor_gt     0.0510
_refine_ls_wR_factor_gt     0.1278
_refine_ls_wR_factor_ref     0.1622
_refine_ls_goodness_of_fit_ref     0.886
_refine_ls_restrained_S_all     0.886
_refine_ls_number_reflns     2434
_refine_ls_number_parameters     171
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.0862P)²+0.05P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.145
_refine_diff_density_min     -0.128
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997a)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material
                       'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
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 0.08696(18) 1.1798(5) 0.09097(8) 0.0467(6) Uani d . 1 . .
    H H1A 0.0731 1.1599 0.0561 0.056 Uiso calc R 1 . .
    O O1 0.15356(17) 0.9487(4) 0.00438(7) 0.0629(6) Uani d . 1 . .
    H H1B 0.1573 0.9094 -0.0271 0.094 Uiso calc R 1 . .
    O O2 0.19698(17) 1.0424(4) 0.17269(7) 0.0584(6) Uani d . 1 . .
    N N2 -0.1750(2) 1.0794(5) 0.09991(9) 0.0511(6) Uani d . 1 . .
    C C1 0.2431(2) 0.7951(6) 0.03973(10) 0.0465(7) Uani d . 1 . .
    C C6 0.2554(2) 0.8271(5) 0.09591(10) 0.0409(6) Uani d . 1 . .
    C C5 0.3467(2) 0.6628(6) 0.13035(11) 0.0500(7) Uani d . 1 . .
    H H5A 0.3549 0.6798 0.1679 0.060 Uiso calc R 1 . .
    C C2 0.3217(3) 0.6055(7) 0.02009(12) 0.0587(8) Uani d . 1 . .
    H H2B 0.3135 0.5840 -0.0174 0.070 Uiso calc R 1 . .
    C C7 0.1783(2) 1.0254(5) 0.12258(10) 0.0427(6) Uani d . 1 . .
    C C8 0.0109(2) 1.3799(6) 0.11431(12) 0.0527(7) Uani d . 1 . .
    H H8A -0.0259 1.5202 0.0868 0.063 Uiso calc R 1 . .
    H H8B 0.0651 1.4832 0.1440 0.063 Uiso calc R 1 . .
    C C9 -0.0930(2) 1.2358(5) 0.13541(10) 0.0449(7) Uani d . 1 . .
    C C10 -0.1043(3) 1.2657(7) 0.18849(12) 0.0660(9) Uani d . 1 . .
    H H10A -0.0460 1.3751 0.2129 0.079 Uiso calc R 1 . .
    C C3 0.4114(3) 0.4495(6) 0.05536(13) 0.0612(8) Uani d . 1 . .
    H H3A 0.4636 0.3238 0.0416 0.073 Uiso calc R 1 . .
    C C11 -0.2032(3) 1.1316(9) 0.20538(13) 0.0775(10) Uani d . 1 . .
    H H11A -0.2126 1.1515 0.2412 0.093 Uiso calc R 1 . .
    C C13 -0.2695(3) 0.9513(7) 0.11734(13) 0.0652(8) Uani d . 1 . .
    H H13A -0.3269 0.8424 0.0924 0.078 Uiso calc R 1 . .
    C C4 0.4250(3) 0.4769(6) 0.11091(13) 0.0590(8) Uani d . 1 . .
    H H4A 0.4860 0.3714 0.1348 0.071 Uiso calc R 1 . .
    C C12 -0.2866(3) 0.9706(7) 0.16912(14) 0.0699(9) Uani d . 1 . .
    H H12A -0.3534 0.8765 0.1795 0.084 Uiso calc R 1 . .
    O O1W 0.4320(2) 0.1529(5) 0.24401(10) 0.0716(6) Uani d D 1 . .
    H H2W 0.3624(18) 0.128(8) 0.2214(11) 0.094(13) Uiso d D 1 . .
    H H1W 0.475(3) -0.003(5) 0.2490(16) 0.103(14) Uiso d D 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.0432(12) 0.0560(14) 0.0403(12) 0.0004(11) 0.0079(10) -0.0035(11)
    O1 0.0527(12) 0.0989(15) 0.0360(10) 0.0150(11) 0.0071(9) -0.0024(11)
    O2 0.0552(12) 0.0806(14) 0.0379(11) 0.0057(10) 0.0069(9) -0.0050(10)
    N2 0.0507(14) 0.0627(14) 0.0417(13) -0.0044(12) 0.0140(11) -0.0037(12)
    C1 0.0367(14) 0.0583(17) 0.0433(16) -0.0049(13) 0.0061(12) -0.0004(14)
    C6 0.0350(13) 0.0451(15) 0.0419(15) -0.0090(11) 0.0062(11) -0.0020(12)
    C5 0.0514(16) 0.0557(16) 0.0418(15) -0.0024(14) 0.0073(13) 0.0023(14)
    C2 0.0501(17) 0.080(2) 0.0498(17) 0.0008(16) 0.0187(14) -0.0065(16)
    C7 0.0368(14) 0.0499(16) 0.0407(15) -0.0102(12) 0.0068(12) 0.0005(13)
    C8 0.0510(17) 0.0499(16) 0.0578(18) 0.0026(13) 0.0131(14) -0.0018(14)
    C9 0.0433(15) 0.0489(16) 0.0415(16) 0.0084(12) 0.0068(12) -0.0009(13)
    C10 0.0608(19) 0.087(2) 0.0483(18) 0.0047(17) 0.0082(15) -0.0100(17)
    C3 0.0530(18) 0.0623(19) 0.074(2) 0.0022(15) 0.0267(16) -0.0086(17)
    C11 0.074(2) 0.117(3) 0.0492(18) 0.018(2) 0.0299(18) 0.006(2)
    C13 0.0527(18) 0.076(2) 0.068(2) -0.0099(16) 0.0157(16) -0.0030(17)
    C4 0.0526(18) 0.0579(18) 0.066(2) 0.0064(14) 0.0127(15) 0.0055(16)
    C12 0.058(2) 0.088(2) 0.070(2) 0.0066(17) 0.0286(17) 0.015(2)
    O1W 0.0620(15) 0.0675(16) 0.0752(16) -0.0019(13) -0.0075(12) -0.0134(13)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 . 1.336(3) ?
    N1 C8 . 1.446(3) ?
    N1 H1A . 0.8600 ?
    O1 C1 . 1.365(3) ?
    O1 H1B . 0.8200 ?
    O2 C7 . 1.232(3) ?
    N2 C9 . 1.330(3) ?
    N2 C13 . 1.337(3) ?
    C1 C2 . 1.387(4) ?
    C1 C6 . 1.395(3) ?
    C6 C5 . 1.392(3) ?
    C6 C7 . 1.494(4) ?
    C5 C4 . 1.371(4) ?
    C5 H5A . 0.9300 ?
    C2 C3 . 1.371(4) ?
    C2 H2B . 0.9300 ?
    C8 C9 . 1.501(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.371(4) ?
    C10 C11 . 1.384(4) ?
    C10 H10A . 0.9300 ?
    C3 C4 . 1.375(4) ?
    C3 H3A . 0.9300 ?
    C11 C12 . 1.359(4) ?
    C11 H11A . 0.9300 ?
    C13 C12 . 1.355(4) ?
    C13 H13A . 0.9300 ?
    C4 H4A . 0.9300 ?
    C12 H12A . 0.9300 ?
    O1W H2W . 0.85(2) ?
    O1W H1W . 0.85(3) ?
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 . . 121.2(2) ?
    C7 N1 H1A . . 119.4 ?
    C8 N1 H1A . . 119.4 ?
    C1 O1 H1B . . 109.5 ?
    C9 N2 C13 . . 118.2(2) ?
    O1 C1 C2 . . 120.3(2) ?
    O1 C1 C6 . . 120.0(2) ?
    C2 C1 C6 . . 119.6(3) ?
    C5 C6 C1 . . 118.0(2) ?
    C5 C6 C7 . . 116.7(2) ?
    C1 C6 C7 . . 125.3(2) ?
    C4 C5 C6 . . 122.3(3) ?
    C4 C5 H5A . . 118.8 ?
    C6 C5 H5A . . 118.8 ?
    C3 C2 C1 . . 120.6(3) ?
    C3 C2 H2B . . 119.7 ?
    C1 C2 H2B . . 119.7 ?
    O2 C7 N1 . . 120.6(2) ?
    O2 C7 C6 . . 120.8(2) ?
    N1 C7 C6 . . 118.6(2) ?
    N1 C8 C9 . . 113.3(2) ?
    N1 C8 H8A . . 108.9 ?
    C9 C8 H8A . . 108.9 ?
    N1 C8 H8B . . 108.9 ?
    C9 C8 H8B . . 108.9 ?
    H8A C8 H8B . . 107.7 ?
    N2 C9 C10 . . 121.2(2) ?
    N2 C9 C8 . . 116.8(2) ?
    C10 C9 C8 . . 122.0(3) ?
    C9 C10 C11 . . 119.4(3) ?
    C9 C10 H10A . . 120.3 ?
    C11 C10 H10A . . 120.3 ?
    C2 C3 C4 . . 120.7(3) ?
    C2 C3 H3A . . 119.6 ?
    C4 C3 H3A . . 119.6 ?
    C12 C11 C10 . . 119.3(3) ?
    C12 C11 H11A . . 120.3 ?
    C10 C11 H11A . . 120.3 ?
    N2 C13 C12 . . 123.9(3) ?
    N2 C13 H13A . . 118.0 ?
    C12 C13 H13A . . 118.0 ?
    C5 C4 C3 . . 118.7(3) ?
    C5 C4 H4A . . 120.7 ?
    C3 C4 H4A . . 120.7 ?
    C13 C12 C11 . . 118.0(3) ?
    C13 C12 H12A . . 121.0 ?
    C11 C12 H12A . . 121.0 ?
    H2W O1W H1W . . 111(4) ?
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
    O1 C1 C6 C5 . . . . 179.0(2) ?
    C2 C1 C6 C5 . . . . -0.5(4) ?
    O1 C1 C6 C7 . . . . -1.2(4) ?
    C2 C1 C6 C7 . . . . 179.3(2) ?
    C1 C6 C5 C4 . . . . 1.0(4) ?
    C7 C6 C5 C4 . . . . -178.8(2) ?
    O1 C1 C2 C3 . . . . -179.7(2) ?
    C6 C1 C2 C3 . . . . -0.1(4) ?
    C8 N1 C7 O2 . . . . 2.7(4) ?
    C8 N1 C7 C6 . . . . -178.7(2) ?
    C5 C6 C7 O2 . . . . 0.8(3) ?
    C1 C6 C7 O2 . . . . -179.0(2) ?
    C5 C6 C7 N1 . . . . -177.8(2) ?
    C1 C6 C7 N1 . . . . 2.3(4) ?
    C7 N1 C8 C9 . . . . -80.1(3) ?
    C13 N2 C9 C10 . . . . 0.1(4) ?
    C13 N2 C9 C8 . . . . -179.2(2) ?
    N1 C8 C9 N2 . . . . -57.4(3) ?
    N1 C8 C9 C10 . . . . 123.3(3) ?
    N2 C9 C10 C11 . . . . -0.3(4) ?
    C8 C9 C10 C11 . . . . 178.9(3) ?
    C1 C2 C3 C4 . . . . 0.3(4) ?
    C9 C10 C11 C12 . . . . 0.6(5) ?
    C9 N2 C13 C12 . . . . -0.2(4) ?
    C6 C5 C4 C3 . . . . -0.8(4) ?
    C2 C3 C4 C5 . . . . 0.2(4) ?
    N2 C13 C12 C11 . . . . 0.5(5) ?
    C10 C11 C12 C13 . . . . -0.7(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1A O1 . . 1_555 0.86 1.97 2.659(3) 136 yes
    C5 H5A O2 . . 1_555 0.93 2.42 2.758(3) 101 yes
    O1 H1B N2 . . 3_575 0.82 1.88 2.680(3) 165 yes
    O1W H1W O1W . . 2_645 0.85(3) 1.87(3) 2.728(3) 177(4) yes
    O1W H2W O2 . . 1_545 0.85(2) 1.98(2) 2.827(3) 175(3) yes
    C12 H12A O1W . . 2_555 0.93 2.49 3.300(4) 146 yes
