##############################################################################
###                                                                        ###
###        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     SHELXL97
_journal_date_recd_electronic     2006-12-12
_journal_date_accepted     2006-12-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      2
_journal_page_first     o474
_journal_page_last     o475
_journal_paper_category     EO
_journal_coeditor_code     DN2109
_publ_contact_author_name     'Mr Jian-Guo Chang'
_publ_contact_author_address
;
Department of Materials Science and Chemical Engineering
Taishan University
271021 Taian
Shandong
People's Republic of China
;
_publ_contact_author_email     tsucjg@163.com
_publ_contact_author_fax     '+86 538 6715156'
_publ_contact_author_phone     '+86 538 6715156'
_publ_section_title
;\
N'-[(1E)-(5-Chloro-2-hydroxyphenyl)(phenyl)methylene]-2-\
hydroxybenzohydrazide
;
loop_
    _publ_author_name
    _publ_author_address
    'Jian-Guo Chang'
;
Department of Materials Science and Chemical Engineering
Taishan University
271021 Taian
Shandong
People's Republic of China
;
    'Ying Cheng'
;
Jinan Petrochemical Design Insititute
250100 Jian
Shandong
People's Republic of China
;
    'Xi-Tao He'
;
Department of Materials Science and Chemical Engineering
Taishan University
271021 Taian
Shandong
People's Republic of China
;
data_I
_chemical_name_systematic
;
N'-[(1E)-(5-Chloro-2-hydroxyphenyl)(phenyl)methylene]-2-hydroxybenzohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H15 Cl N2 O3'
_chemical_formula_sum     'C20 H15 Cl N2 O3'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C20 H15 Cl N2 O3'
_chemical_formula_weight     366.79
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     15.3237(6)
_cell_length_b     12.0171(5)
_cell_length_c     20.0773(8)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3697.2(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5275
_cell_measurement_theta_min     2.38
_cell_measurement_theta_max     21.52
_cell_measurement_temperature     273(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.318
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1520
_exptl_absorpt_coefficient_mu     0.228
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9244
_exptl_absorpt_correction_T_max     0.9776
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     273(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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     39233
_diffrn_reflns_av_R_equivalents     0.0577
_diffrn_reflns_av_sigmaI/netI     0.0237
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     ?
_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     3248
_reflns_number_gt     2261
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0647
_refine_ls_R_factor_gt     0.0395
_refine_ls_wR_factor_gt     0.0967
_refine_ls_wR_factor_ref     0.1152
_refine_ls_goodness_of_fit_ref     1.000
_refine_ls_restrained_S_all     0.997
_refine_ls_number_reflns     3248
_refine_ls_number_parameters     237
_refine_ls_number_restraints     18
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0507P)²+1.2845P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.119
_refine_diff_density_min     -0.218
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_extinction_expression     ?
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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) and PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL'
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
    Cl Cl1 1.09963(5) 0.85633(6) 0.30089(4) 0.0975(3) Uani d . 1 . .
    O O1 0.99237(12) 1.16483(12) 0.09131(8) 0.0717(5) Uani d . 1 . .
    H H1 0.9591 1.1359 0.0644 0.107 Uiso calc R 1 . .
    O O2 0.84619(9) 1.14393(11) -0.05196(7) 0.0563(4) Uani d . 1 . .
    O O3 0.73116(14) 0.83443(13) -0.05047(9) 0.0882(6) Uani d . 1 . .
    H H3 0.7039 0.7763 -0.0555 0.132 Uiso calc R 1 . .
    N N1 0.90070(10) 1.00781(13) 0.04214(8) 0.0498(4) Uani d . 1 . .
    N N2 0.84440(10) 0.97365(13) -0.00650(8) 0.0499(4) Uani d . 1 . .
    H H2 0.8267 0.9058 -0.0080 0.060 Uiso calc R 1 . .
    C C1 1.01537(14) 1.08944(17) 0.13786(10) 0.0539(5) Uani d . 1 . .
    C C2 0.98516(12) 0.97898(15) 0.13790(9) 0.0454(5) Uani d . 1 . .
    C C3 1.01305(13) 0.90851(17) 0.18889(9) 0.0507(5) Uani d . 1 . .
    H H3A 0.9939 0.8351 0.1898 0.061 Uiso calc R 1 . .
    C C4 1.06837(14) 0.94629(19) 0.23773(10) 0.0594(6) Uani d . 1 . .
    C C5 1.09790(15) 1.0544(2) 0.23730(11) 0.0680(6) Uani d . 1 . .
    H H5 1.1353 1.0794 0.2706 0.082 Uiso calc R 1 . .
    C C6 1.07182(15) 1.12493(19) 0.18764(11) 0.0652(6) Uani d . 1 . .
    H H6 1.0922 1.1978 0.1872 0.078 Uiso calc R 1 . .
    C C7 0.92515(12) 0.93681(16) 0.08668(9) 0.0450(5) Uani d . 1 . .
    C C8 0.89440(13) 0.81937(16) 0.08701(9) 0.0480(5) Uani d . 1 . .
    C C9 0.81224(15) 0.7930(2) 0.10964(12) 0.0711(7) Uani d . 1 . .
    H H9 0.7767 0.8487 0.1270 0.085 Uiso calc R 1 . .
    C C10 0.78195(19) 0.6851(3) 0.10696(16) 0.0918(9) Uani d . 1 . .
    H H10 0.7264 0.6682 0.1226 0.110 Uiso calc R 1 . .
    C C11 0.8329(2) 0.6040(3) 0.08172(15) 0.0930(10) Uani d U 1 . .
    H H11 0.8119 0.5316 0.0791 0.112 Uiso calc R 1 . .
    C C12 0.9149(2) 0.6275(2) 0.06003(15) 0.0971(9) Uani d U 1 . .
    H H12 0.9502 0.5708 0.0437 0.116 Uiso calc R 1 . .
    C C13 0.94613(17) 0.73602(19) 0.06226(12) 0.0720(7) Uani d U 1 . .
    H H13 1.0020 0.7521 0.0470 0.086 Uiso calc R 1 . .
    C C14 0.81715(13) 1.04834(16) -0.05220(9) 0.0459(5) Uani d . 1 . .
    C C15 0.75267(13) 1.00895(15) -0.10192(9) 0.0469(5) Uani d . 1 . .
    C C16 0.71261(14) 0.90519(16) -0.10126(10) 0.0557(5) Uani d . 1 . .
    C C17 0.65505(15) 0.87517(19) -0.15125(12) 0.0679(6) Uani d . 1 . .
    H H17 0.6283 0.8057 -0.1501 0.081 Uiso calc R 1 . .
    C C18 0.63731(17) 0.9473(2) -0.20245(13) 0.0760(7) Uani d . 1 . .
    H H18 0.5992 0.9265 -0.2362 0.091 Uiso calc R 1 . .
    C C19 0.67607(17) 1.0507(2) -0.20376(12) 0.0774(7) Uani d . 1 . .
    H H19 0.6639 1.0999 -0.2383 0.093 Uiso calc R 1 . .
    C C20 0.73247(15) 1.08075(18) -0.15421(11) 0.0618(6) Uani d . 1 . .
    H H20 0.7580 1.1509 -0.1554 0.074 Uiso calc R 1 . .
_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
    Cl1 C4 . 1.734(2) ?
    O1 C1 . 1.349(2) ?
    O1 H1 . 0.8200 ?
    O2 C14 . 1.232(2) ?
    O3 C16 . 1.358(2) ?
    O3 H3 . 0.8200 ?
    N1 C7 . 1.292(2) ?
    N1 N2 . 1.366(2) ?
    N2 C14 . 1.350(2) ?
    N2 H2 . 0.8600 ?
    C1 C6 . 1.389(3) ?
    C1 C2 . 1.406(3) ?
    C2 C3 . 1.396(3) ?
    C2 C7 . 1.470(3) ?
    C3 C4 . 1.373(3) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.376(3) ?
    C5 C6 . 1.368(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.488(3) ?
    C8 C13 . 1.371(3) ?
    C8 C9 . 1.375(3) ?
    C9 C10 . 1.379(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.347(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.360(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.390(4) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.482(3) ?
    C15 C16 . 1.390(3) ?
    C15 C20 . 1.394(3) ?
    C16 C17 . 1.384(3) ?
    C17 C18 . 1.372(3) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.377(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.366(3) ?
    C19 H19 . 0.9300 ?
    C20 H20 . 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
    C1 O1 H1 . . 109.5 ?
    C16 O3 H3 . . 109.5 ?
    C7 N1 N2 . . 118.66(16) ?
    C14 N2 N1 . . 118.78(16) ?
    C14 N2 H2 . . 120.6 ?
    N1 N2 H2 . . 120.6 ?
    O1 C1 C6 . . 117.08(19) ?
    O1 C1 C2 . . 123.27(18) ?
    C6 C1 C2 . . 119.6(2) ?
    C3 C2 C1 . . 118.19(18) ?
    C3 C2 C7 . . 119.71(17) ?
    C1 C2 C7 . . 122.09(17) ?
    C4 C3 C2 . . 120.80(19) ?
    C4 C3 H3A . . 119.6 ?
    C2 C3 H3A . . 119.6 ?
    C3 C4 C5 . . 120.7(2) ?
    C3 C4 Cl1 . . 119.11(17) ?
    C5 C4 Cl1 . . 120.16(17) ?
    C6 C5 C4 . . 119.6(2) ?
    C6 C5 H5 . . 120.2 ?
    C4 C5 H5 . . 120.2 ?
    C5 C6 C1 . . 121.1(2) ?
    C5 C6 H6 . . 119.5 ?
    C1 C6 H6 . . 119.5 ?
    N1 C7 C2 . . 115.99(17) ?
    N1 C7 C8 . . 122.53(17) ?
    C2 C7 C8 . . 121.48(16) ?
    C13 C8 C9 . . 118.8(2) ?
    C13 C8 C7 . . 120.56(19) ?
    C9 C8 C7 . . 120.64(19) ?
    C8 C9 C10 . . 120.8(3) ?
    C8 C9 H9 . . 119.6 ?
    C10 C9 H9 . . 119.6 ?
    C11 C10 C9 . . 120.0(3) ?
    C11 C10 H10 . . 120.0 ?
    C9 C10 H10 . . 120.0 ?
    C10 C11 C12 . . 120.4(3) ?
    C10 C11 H11 . . 119.8 ?
    C12 C11 H11 . . 119.8 ?
    C11 C12 C13 . . 120.2(3) ?
    C11 C12 H12 . . 119.9 ?
    C13 C12 H12 . . 119.9 ?
    C8 C13 C12 . . 119.9(3) ?
    C8 C13 H13 . . 120.1 ?
    C12 C13 H13 . . 120.1 ?
    O2 C14 N2 . . 120.37(18) ?
    O2 C14 C15 . . 122.77(17) ?
    N2 C14 C15 . . 116.85(17) ?
    C16 C15 C20 . . 117.68(18) ?
    C16 C15 C14 . . 125.06(17) ?
    C20 C15 C14 . . 117.24(18) ?
    O3 C16 C17 . . 120.98(19) ?
    O3 C16 C15 . . 118.46(18) ?
    C17 C16 C15 . . 120.56(18) ?
    C18 C17 C16 . . 120.3(2) ?
    C18 C17 H17 . . 119.8 ?
    C16 C17 H17 . . 119.8 ?
    C17 C18 C19 . . 119.9(2) ?
    C17 C18 H18 . . 120.0 ?
    C19 C18 H18 . . 120.0 ?
    C20 C19 C18 . . 119.8(2) ?
    C20 C19 H19 . . 120.1 ?
    C18 C19 H19 . . 120.1 ?
    C19 C20 C15 . . 121.7(2) ?
    C19 C20 H20 . . 119.2 ?
    C15 C20 H20 . . 119.2 ?
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
    C7 N1 N2 C14 . . . . 178.47(17) ?
    O1 C1 C2 C3 . . . . -179.66(19) ?
    C6 C1 C2 C3 . . . . 0.4(3) ?
    O1 C1 C2 C7 . . . . -0.2(3) ?
    C6 C1 C2 C7 . . . . 179.79(18) ?
    C1 C2 C3 C4 . . . . 0.1(3) ?
    C7 C2 C3 C4 . . . . -179.30(18) ?
    C2 C3 C4 C5 . . . . -0.3(3) ?
    C2 C3 C4 Cl1 . . . . 178.83(15) ?
    C3 C4 C5 C6 . . . . 0.0(4) ?
    Cl1 C4 C5 C6 . . . . -179.15(18) ?
    C4 C5 C6 C1 . . . . 0.5(4) ?
    O1 C1 C6 C5 . . . . 179.3(2) ?
    C2 C1 C6 C5 . . . . -0.7(3) ?
    N2 N1 C7 C2 . . . . -179.53(15) ?
    N2 N1 C7 C8 . . . . 0.0(3) ?
    C3 C2 C7 N1 . . . . 178.37(17) ?
    C1 C2 C7 N1 . . . . -1.0(3) ?
    C3 C2 C7 C8 . . . . -1.2(3) ?
    C1 C2 C7 C8 . . . . 179.41(18) ?
    N1 C7 C8 C13 . . . . 100.0(2) ?
    C2 C7 C8 C13 . . . . -80.5(2) ?
    N1 C7 C8 C9 . . . . -77.3(3) ?
    C2 C7 C8 C9 . . . . 102.2(2) ?
    C13 C8 C9 C10 . . . . -0.6(3) ?
    C7 C8 C9 C10 . . . . 176.8(2) ?
    C8 C9 C10 C11 . . . . -0.3(4) ?
    C9 C10 C11 C12 . . . . 1.3(4) ?
    C10 C11 C12 C13 . . . . -1.5(4) ?
    C9 C8 C13 C12 . . . . 0.4(3) ?
    C7 C8 C13 C12 . . . . -177.0(2) ?
    C11 C12 C13 C8 . . . . 0.6(4) ?
    N1 N2 C14 O2 . . . . 3.8(3) ?
    N1 N2 C14 C15 . . . . -176.99(16) ?
    O2 C14 C15 C16 . . . . -174.5(2) ?
    N2 C14 C15 C16 . . . . 6.3(3) ?
    O2 C14 C15 C20 . . . . 7.1(3) ?
    N2 C14 C15 C20 . . . . -172.09(18) ?
    C20 C15 C16 O3 . . . . -179.6(2) ?
    C14 C15 C16 O3 . . . . 2.0(3) ?
    C20 C15 C16 C17 . . . . 0.3(3) ?
    C14 C15 C16 C17 . . . . -178.1(2) ?
    O3 C16 C17 C18 . . . . -179.6(2) ?
    C15 C16 C17 C18 . . . . 0.5(4) ?
    C16 C17 C18 C19 . . . . -0.8(4) ?
    C17 C18 C19 C20 . . . . 0.4(4) ?
    C18 C19 C20 C15 . . . . 0.4(4) ?
    C16 C15 C20 C19 . . . . -0.7(3) ?
    C14 C15 C20 C19 . . . . 177.8(2) ?
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
    _geom_hbond_publ_flag
    O1 H1 N1 . 0.820 1.835 2.5510(10)
                                    145.05 y
    N2 H2 O3 . 0.860 1.899 2.5670(10)
                                    133.43 y
    O3 H3 O2 8_755 0.820 1.768 2.5780(10)
                                        169.23 y
