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###                                                                        ###
###        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/  #
# cif/home.html                                                              #
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data_global
_audit_creation_method     ?
_journal_date_recd_electronic     2008-01-04
_journal_date_accepted     2008-01-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o471
_journal_page_last     o471
_journal_paper_category     QO
_journal_coeditor_code     SU2040
_publ_contact_author_name     'Nie, Yi'
_publ_contact_author_address
;
Department of Chemistry
Qufu Normal University
Qufu 273165
People's Republic of China
;
_publ_contact_author_email     nieyi68@126.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
<i>N</i>'-[4-(Dimethylamino)benzylidene]3-hydroxybenzohydrazide
;
loop_
    _publ_author_name
    _publ_author_address
    'Nie, Yi'
;
Department of Chemistry
Qufu Normal University
Qufu 273165
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N'-[4-(Dimethylamino)benzylidene]3-hydroxybenzohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H17 N3 O2'
_chemical_formula_sum     'C16 H17 N3 O2'
_chemical_formula_iupac     'C16 H17 N3 O2'
_chemical_formula_weight     283.33
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     13.397(3)
_cell_length_b     9.663(2)
_cell_length_c     11.183(2)
_cell_angle_alpha     90.00
_cell_angle_beta     101.97(3)
_cell_angle_gamma     90.00
_cell_volume     1416.2(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4593
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     27.7
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.329
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9753
_exptl_absorpt_correction_T_max     0.9761
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     298(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
                                'Bruker SMART APEX area-detector diffractometer'
_diffrn_measurement_method     '\w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11531
_diffrn_reflns_av_R_equivalents     0.0209
_diffrn_reflns_av_sigmaI/netI     0.0216
_diffrn_reflns_theta_min     2.62
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     o
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     o
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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     3094
_reflns_number_gt     2579
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0521
_refine_ls_R_factor_gt     0.0444
_refine_ls_wR_factor_gt     0.1233
_refine_ls_wR_factor_ref     0.1303
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.047
_refine_ls_number_reflns     3094
_refine_ls_number_parameters     196
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.1729P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     0.211
_refine_diff_density_min     -0.289
_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 (Siemens, 1996)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Version 5.1; Sheldrick, 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.51231(8) 0.27675(11) 0.29293(9) 0.0574(3) Uani d . 1 . .
    O O2 0.28657(7) 0.69755(10) 0.22473(9) 0.0486(3) Uani d . 1 . .
    H H2 0.3315 0.7006 0.1849 0.073 Uiso calc R 1 . .
    N N1 0.97117(10) -0.30631(15) 0.63913(13) 0.0654(4) Uani d . 1 . .
    N N2 0.60441(8) 0.13189(10) 0.48763(10) 0.0416(3) Uani d . 1 . .
    N N3 0.52359(8) 0.22033(11) 0.49046(10) 0.0420(3) Uani d D 1 . .
    C C1 0.72192(9) -0.03254(12) 0.59700(11) 0.0379(3) Uani d . 1 . .
    C C2 0.78863(10) -0.03161(13) 0.51647(11) 0.0430(3) Uani d . 1 . .
    H H2A 0.7774 0.0302 0.4513 0.052 Uiso calc R 1 . .
    C C3 0.87041(10) -0.11981(14) 0.53134(12) 0.0445(3) Uani d . 1 . .
    H H3 0.9138 -0.1157 0.4764 0.053 Uiso calc R 1 . .
    C C4 0.89036(9) -0.21613(13) 0.62715(12) 0.0425(3) Uani d . 1 . .
    C C5 0.82405(10) -0.21577(14) 0.70911(12) 0.0456(3) Uani d . 1 . .
    H H5 0.8352 -0.2770 0.7747 0.055 Uiso calc R 1 . .
    C C6 0.74284(10) -0.12595(14) 0.69358(11) 0.0424(3) Uani d . 1 . .
    H H6 0.7004 -0.1277 0.7496 0.051 Uiso calc R 1 . .
    C C7 0.99119(16) -0.4061(2) 0.73523(17) 0.0793(6) Uani d . 1 . .
    H H7A 1.0129 -0.3597 0.8121 0.119 Uiso calc R 1 . .
    H H7B 1.0439 -0.4679 0.7219 0.119 Uiso calc R 1 . .
    H H7C 0.9302 -0.4578 0.7363 0.119 Uiso calc R 1 . .
    C C8 1.04154(15) -0.2992(2) 0.5584(2) 0.0903(7) Uani d . 1 . .
    H H8A 1.0063 -0.3194 0.4764 0.135 Uiso calc R 1 . .
    H H8B 1.0952 -0.3655 0.5835 0.135 Uiso calc R 1 . .
    H H8C 1.0702 -0.2079 0.5612 0.135 Uiso calc R 1 . .
    C C9 0.63422(9) 0.05897(13) 0.58348(11) 0.0411(3) Uani d . 1 . .
    H H9 0.5988 0.0645 0.6466 0.049 Uiso calc R 1 . .
    C C10 0.48449(9) 0.29458(12) 0.38962(12) 0.0397(3) Uani d . 1 . .
    C C11 0.40510(9) 0.39961(12) 0.40150(11) 0.0375(3) Uani d . 1 . .
    C C12 0.38258(9) 0.49733(12) 0.30887(11) 0.0375(3) Uani d . 1 . .
    H H12 0.4168 0.4954 0.2446 0.045 Uiso calc R 1 . .
    C C13 0.30939(9) 0.59770(12) 0.31174(11) 0.0380(3) Uani d . 1 . .
    C C14 0.25681(10) 0.59887(14) 0.40629(12) 0.0453(3) Uani d . 1 . .
    H H14 0.2067 0.6651 0.4080 0.054 Uiso calc R 1 . .
    C C15 0.27927(11) 0.50121(16) 0.49776(13) 0.0530(4) Uani d . 1 . .
    H H15 0.2440 0.5021 0.5611 0.064 Uiso calc R 1 . .
    C C16 0.35350(10) 0.40181(14) 0.49689(12) 0.0469(3) Uani d . 1 . .
    H H16 0.3686 0.3372 0.5596 0.056 Uiso calc R 1 . .
    H H3A 0.5095(14) 0.2388(19) 0.5637(11) 0.080 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
    O1 0.0646(6) 0.0592(6) 0.0572(6) 0.0197(5) 0.0327(5) 0.0044(5)
    O2 0.0480(5) 0.0487(5) 0.0530(6) 0.0081(4) 0.0192(4) 0.0094(4)
    N1 0.0552(7) 0.0751(9) 0.0698(8) 0.0289(7) 0.0219(6) 0.0220(7)
    N2 0.0369(5) 0.0388(6) 0.0501(6) 0.0050(4) 0.0114(4) -0.0082(4)
    N3 0.0380(5) 0.0417(6) 0.0485(6) 0.0072(4) 0.0137(5) -0.0065(5)
    C1 0.0368(6) 0.0382(6) 0.0391(6) -0.0001(5) 0.0087(5) -0.0057(5)
    C2 0.0452(7) 0.0451(7) 0.0400(6) 0.0056(5) 0.0115(5) 0.0069(5)
    C3 0.0427(7) 0.0535(8) 0.0407(7) 0.0056(5) 0.0162(5) 0.0024(5)
    C4 0.0388(6) 0.0447(7) 0.0432(7) 0.0046(5) 0.0067(5) 0.0001(5)
    C5 0.0467(7) 0.0504(7) 0.0397(7) 0.0023(6) 0.0085(5) 0.0086(5)
    C6 0.0428(7) 0.0499(7) 0.0373(6) -0.0026(5) 0.0149(5) -0.0027(5)
    C7 0.0834(12) 0.0834(13) 0.0713(11) 0.0421(10) 0.0162(9) 0.0196(9)
    C8 0.0656(11) 0.1028(15) 0.1139(16) 0.0410(11) 0.0449(11) 0.0305(13)
    C9 0.0394(6) 0.0403(6) 0.0456(7) 0.0004(5) 0.0131(5) -0.0074(5)
    C10 0.0359(6) 0.0369(6) 0.0497(7) 0.0000(5) 0.0165(5) -0.0046(5)
    C11 0.0332(6) 0.0371(6) 0.0442(7) -0.0012(5) 0.0122(5) -0.0055(5)
    C12 0.0352(6) 0.0394(6) 0.0412(6) -0.0024(5) 0.0156(5) -0.0044(5)
    C13 0.0345(6) 0.0378(6) 0.0423(6) -0.0024(5) 0.0095(5) -0.0018(5)
    C14 0.0393(6) 0.0472(7) 0.0530(7) 0.0094(5) 0.0182(5) -0.0002(6)
    C15 0.0532(8) 0.0630(9) 0.0511(8) 0.0150(6) 0.0302(6) 0.0071(6)
    C16 0.0486(7) 0.0502(7) 0.0464(7) 0.0102(6) 0.0199(6) 0.0079(6)
_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
    O1 C10 . 1.2267(15) ?
    O2 C13 . 1.3593(15) ?
    O2 H2 . 0.8200 ?
    N1 C4 . 1.3745(17) ?
    N1 C7 . 1.427(2) ?
    N1 C8 . 1.436(2) ?
    N2 C9 . 1.2757(16) ?
    N2 N3 . 1.3848(14) ?
    N3 C10 . 1.3475(17) ?
    N3 H3A . 0.895(9) ?
    C1 C6 . 1.3907(17) ?
    C1 C2 . 1.3942(17) ?
    C1 C9 . 1.4531(17) ?
    C2 C3 . 1.3706(17) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.4025(18) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.4025(19) ?
    C5 C6 . 1.3744(18) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.4958(16) ?
    C11 C16 . 1.3864(18) ?
    C11 C12 . 1.3878(17) ?
    C12 C13 . 1.3842(17) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.3868(17) ?
    C14 C15 . 1.3783(19) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.3841(18) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
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
    C13 O2 H2 . . 109.5 ?
    C4 N1 C7 . . 121.53(13) ?
    C4 N1 C8 . . 120.99(13) ?
    C7 N1 C8 . . 117.43(13) ?
    C9 N2 N3 . . 115.57(10) ?
    C10 N3 N2 . . 118.66(10) ?
    C10 N3 H3A . . 122.7(12) ?
    N2 N3 H3A . . 117.2(12) ?
    C6 C1 C2 . . 116.93(11) ?
    C6 C1 C9 . . 120.27(11) ?
    C2 C1 C9 . . 122.80(11) ?
    C3 C2 C1 . . 121.39(12) ?
    C3 C2 H2A . . 119.3 ?
    C1 C2 H2A . . 119.3 ?
    C2 C3 C4 . . 121.75(11) ?
    C2 C3 H3 . . 119.1 ?
    C4 C3 H3 . . 119.1 ?
    N1 C4 C5 . . 122.05(12) ?
    N1 C4 C3 . . 121.11(12) ?
    C5 C4 C3 . . 116.84(11) ?
    C6 C5 C4 . . 120.73(12) ?
    C6 C5 H5 . . 119.6 ?
    C4 C5 H5 . . 119.6 ?
    C5 C6 C1 . . 122.33(11) ?
    C5 C6 H6 . . 118.8 ?
    C1 C6 H6 . . 118.8 ?
    N1 C7 H7A . . 109.5 ?
    N1 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    N1 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    N1 C8 H8A . . 109.5 ?
    N1 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    N1 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    N2 C9 C1 . . 121.94(11) ?
    N2 C9 H9 . . 119.0 ?
    C1 C9 H9 . . 119.0 ?
    O1 C10 N3 . . 121.76(11) ?
    O1 C10 C11 . . 121.68(12) ?
    N3 C10 C11 . . 116.56(10) ?
    C16 C11 C12 . . 119.87(11) ?
    C16 C11 C10 . . 123.77(11) ?
    C12 C11 C10 . . 116.35(10) ?
    C13 C12 C11 . . 120.32(10) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    O2 C13 C12 . . 122.41(10) ?
    O2 C13 C14 . . 117.75(11) ?
    C12 C13 C14 . . 119.84(11) ?
    C15 C14 C13 . . 119.55(11) ?
    C15 C14 H14 . . 120.2 ?
    C13 C14 H14 . . 120.2 ?
    C14 C15 C16 . . 121.09(12) ?
    C14 C15 H15 . . 119.5 ?
    C16 C15 H15 . . 119.5 ?
    C15 C16 C11 . . 119.32(12) ?
    C15 C16 H16 . . 120.3 ?
    C11 C16 H16 . . 120.3 ?
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
    O2 H2 O1 2_655 0.82 2.18 2.8470(14) 138.1
    O2 H2 N2 2_655 0.82 2.36 3.1008(16) 149.9
    N3 H3A O1 4_566 0.895(9) 2.561(11) 3.4172(16) 160.4(16)