##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H16 Cl N3 O2'
_chemical_formula_sum     'C20 H16 Cl N3 O2'
_chemical_formula_weight     365.81
_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     5.3454(9)
_cell_length_b     12.360(2)
_cell_length_c     26.292(4)
_cell_angle_alpha     90.00
_cell_angle_beta     94.994(3)
_cell_angle_gamma     90.00
_cell_volume     1730.5(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2736
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     25.3
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.404
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     760
_exptl_absorpt_coefficient_mu     0.241
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.921
_exptl_absorpt_correction_T_max     0.953
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     294(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 CCD area detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9564
_diffrn_reflns_av_R_equivalents     0.040
_diffrn_reflns_av_sigmaI/netI     0.048
_diffrn_reflns_theta_min     1.6
_diffrn_reflns_theta_max     26.4
_diffrn_reflns_theta_full     26.4
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -32
_diffrn_reflns_limit_l_max     32
_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 > 2σ(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     3542
_reflns_number_gt     2357
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.076
_refine_ls_R_factor_gt     0.042
_refine_ls_wR_factor_gt     0.103
_refine_ls_wR_factor_ref     0.118
_refine_ls_goodness_of_fit_ref     1.01
_refine_ls_restrained_S_all     1.01
_refine_ls_number_reflns     3542
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0630P)²+0.0411P] 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     0.21
_refine_diff_density_min     -0.22
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_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
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 0.23424(11) 0.71742(5) 0.31356(2) 0.04877(19) Uani d . 1 . .
    O O1 0.4847(3) 0.50544(11) 0.26878(5) 0.0396(4) Uani d . 1 . .
    O O2 -0.2293(3) 0.31310(14) -0.02373(5) 0.0541(4) Uani d . 1 . .
    N N1 0.1887(3) 0.36771(14) 0.03897(6) 0.0390(4) Uani d . 1 . .
    N N2 0.1948(3) 0.33651(14) -0.01162(6) 0.0393(4) Uani d . 1 . .
    H H2 0.3349 0.3358 -0.0254 0.047 Uiso calc R 1 . .
    N N3 0.0445(4) 0.19320(16) -0.19219(7) 0.0504(5) Uani d . 1 . .
    C C1 0.4228(4) 0.64991(16) 0.36025(7) 0.0369(5) Uani d . 1 . .
    C C2 0.3682(5) 0.66062(19) 0.41075(8) 0.0498(6) Uani d . 1 . .
    H H2A 0.2335 0.7027 0.4190 0.060 Uiso calc R 1 . .
    C C3 0.5170(6) 0.6079(2) 0.44822(9) 0.0636(8) Uani d . 1 . .
    H H3 0.4817 0.6139 0.4821 0.076 Uiso calc R 1 . .
    C C4 0.7169(6) 0.5464(2) 0.43603(9) 0.0655(8) Uani d . 1 . .
    H H4 0.8168 0.5114 0.4617 0.079 Uiso calc R 1 . .
    C C5 0.7707(5) 0.53603(19) 0.38578(9) 0.0525(6) Uani d . 1 . .
    H H5 0.9063 0.4939 0.3780 0.063 Uiso calc R 1 . .
    C C6 0.6244(4) 0.58793(16) 0.34656(7) 0.0362(5) Uani d . 1 . .
    C C7 0.6794(4) 0.57386(17) 0.29199(7) 0.0379(5) Uani d . 1 . .
    H H7A 0.6786 0.6433 0.2748 0.046 Uiso calc R 1 . .
    H H7B 0.8426 0.5405 0.2901 0.046 Uiso calc R 1 . .
    C C8 0.4772(4) 0.48520(15) 0.21743(7) 0.0305(4) Uani d . 1 . .
    C C9 0.6565(4) 0.51990(15) 0.18576(7) 0.0328(5) Uani d . 1 . .
    H H9 0.7932 0.5610 0.1987 0.039 Uiso calc R 1 . .
    C C10 0.6278(4) 0.49200(15) 0.13442(7) 0.0326(5) Uani d . 1 . .
    H H10 0.7495 0.5132 0.1133 0.039 Uiso calc R 1 . .
    C C11 0.4216(4) 0.43309(15) 0.11386(7) 0.0309(4) Uani d . 1 . .
    C C12 0.2450(4) 0.39907(16) 0.14678(7) 0.0341(5) Uani d . 1 . .
    H H12 0.1066 0.3589 0.1339 0.041 Uiso calc R 1 . .
    C C13 0.2728(4) 0.42407(16) 0.19781(7) 0.0336(5) Uani d . 1 . .
    H H13 0.1549 0.4001 0.2193 0.040 Uiso calc R 1 . .
    C C14 0.3958(4) 0.40478(16) 0.05991(7) 0.0356(5) Uani d . 1 . .
    H H14 0.5315 0.4138 0.0405 0.043 Uiso calc R 1 . .
    C C15 -0.0197(4) 0.30727(16) -0.03909(7) 0.0352(5) Uani d . 1 . .
    C C16 0.0153(4) 0.26728(15) -0.09221(7) 0.0311(5) Uani d . 1 . .
    C C17 0.2179(4) 0.20694(17) -0.10503(8) 0.0409(5) Uani d . 1 . .
    H H17 0.3487 0.1902 -0.0806 0.049 Uiso calc R 1 . .
    C C18 0.2224(4) 0.17181(19) -0.15504(8) 0.0481(6) Uani d . 1 . .
    H H18 0.3589 0.1305 -0.1631 0.058 Uiso calc R 1 . .
    C C19 -0.1479(5) 0.2520(2) -0.17900(8) 0.0488(6) Uani d . 1 . .
    H H19 -0.2748 0.2686 -0.2043 0.059 Uiso calc R 1 . .
    C C20 -0.1719(4) 0.29002(17) -0.13054(7) 0.0403(5) Uani d . 1 . .
    H H20 -0.3117 0.3304 -0.1236 0.048 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 C1 . 1.733(2) ?
    O1 C8 . 1.370(2) ?
    O1 C7 . 1.435(2) ?
    O2 C15 . 1.226(2) ?
    N1 C14 . 1.277(2) ?
    N1 N2 . 1.388(2) ?
    N2 C15 . 1.350(2) ?
    N2 H2 . 0.8600 ?
    N3 C18 . 1.329(3) ?
    N3 C19 . 1.330(3) ?
    C1 C2 . 1.390(3) ?
    C1 C6 . 1.395(3) ?
    C2 C3 . 1.375(3) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.372(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.382(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.395(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.500(3) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C13 . 1.390(3) ?
    C8 C9 . 1.391(3) ?
    C9 C10 . 1.389(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.391(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.400(3) ?
    C11 C14 . 1.456(3) ?
    C12 C13 . 1.372(3) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.508(3) ?
    C16 C17 . 1.381(3) ?
    C16 C20 . 1.386(3) ?
    C17 C18 . 1.387(3) ?
    C17 H17 . 0.9300 ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.374(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
    C8 O1 C7 . . 118.98(15) ?
    C14 N1 N2 . . 114.87(17) ?
    C15 N2 N1 . . 119.81(17) ?
    C15 N2 H2 . . 120.1 ?
    N1 N2 H2 . . 120.1 ?
    C18 N3 C19 . . 115.91(18) ?
    C2 C1 C6 . . 122.0(2) ?
    C2 C1 Cl1 . . 118.24(18) ?
    C6 C1 Cl1 . . 119.77(15) ?
    C3 C2 C1 . . 118.9(2) ?
    C3 C2 H2A . . 120.6 ?
    C1 C2 H2A . . 120.6 ?
    C4 C3 C2 . . 120.6(2) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    C3 C4 C5 . . 120.4(2) ?
    C3 C4 H4 . . 119.8 ?
    C5 C4 H4 . . 119.8 ?
    C4 C5 C6 . . 121.0(2) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C5 C6 C1 . . 117.2(2) ?
    C5 C6 C7 . . 120.7(2) ?
    C1 C6 C7 . . 122.05(18) ?
    O1 C7 C6 . . 106.26(16) ?
    O1 C7 H7A . . 110.5 ?
    C6 C7 H7A . . 110.5 ?
    O1 C7 H7B . . 110.5 ?
    C6 C7 H7B . . 110.5 ?
    H7A C7 H7B . . 108.7 ?
    O1 C8 C13 . . 114.81(16) ?
    O1 C8 C9 . . 124.81(17) ?
    C13 C8 C9 . . 120.38(17) ?
    C10 C9 C8 . . 118.78(18) ?
    C10 C9 H9 . . 120.6 ?
    C8 C9 H9 . . 120.6 ?
    C9 C10 C11 . . 121.67(18) ?
    C9 C10 H10 . . 119.2 ?
    C11 C10 H10 . . 119.2 ?
    C10 C11 C12 . . 118.11(17) ?
    C10 C11 C14 . . 120.62(18) ?
    C12 C11 C14 . . 121.23(18) ?
    C13 C12 C11 . . 121.03(18) ?
    C13 C12 H12 . . 119.5 ?
    C11 C12 H12 . . 119.5 ?
    C12 C13 C8 . . 120.00(18) ?
    C12 C13 H13 . . 120.0 ?
    C8 C13 H13 . . 120.0 ?
    N1 C14 C11 . . 120.73(18) ?
    N1 C14 H14 . . 119.6 ?
    C11 C14 H14 . . 119.6 ?
    O2 C15 N2 . . 124.47(18) ?
    O2 C15 C16 . . 120.98(17) ?
    N2 C15 C16 . . 114.54(17) ?
    C17 C16 C20 . . 117.65(18) ?
    C17 C16 C15 . . 124.47(17) ?
    C20 C16 C15 . . 117.86(18) ?
    C16 C17 C18 . . 118.63(19) ?
    C16 C17 H17 . . 120.7 ?
    C18 C17 H17 . . 120.7 ?
    N3 C18 C17 . . 124.4(2) ?
    N3 C18 H18 . . 117.8 ?
    C17 C18 H18 . . 117.8 ?
    N3 C19 C20 . . 124.4(2) ?
    N3 C19 H19 . . 117.8 ?
    C20 C19 H19 . . 117.8 ?
    C19 C20 C16 . . 119.0(2) ?
    C19 C20 H20 . . 120.5 ?
    C16 C20 H20 . . 120.5 ?
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
    C14 N1 N2 C15 . . . . -172.84(18) ?
    C6 C1 C2 C3 . . . . -0.4(3) ?
    Cl1 C1 C2 C3 . . . . -179.72(17) ?
    C1 C2 C3 C4 . . . . 0.5(4) ?
    C2 C3 C4 C5 . . . . -0.4(4) ?
    C3 C4 C5 C6 . . . . 0.3(4) ?
    C4 C5 C6 C1 . . . . -0.2(3) ?
    C4 C5 C6 C7 . . . . -178.3(2) ?
    C2 C1 C6 C5 . . . . 0.3(3) ?
    Cl1 C1 C6 C5 . . . . 179.57(16) ?
    C2 C1 C6 C7 . . . . 178.32(18) ?
    Cl1 C1 C6 C7 . . . . -2.4(3) ?
    C8 O1 C7 C6 . . . . 175.26(16) ?
    C5 C6 C7 O1 . . . . 106.9(2) ?
    C1 C6 C7 O1 . . . . -71.1(2) ?
    C7 O1 C8 C13 . . . . -175.94(17) ?
    C7 O1 C8 C9 . . . . 4.9(3) ?
    O1 C8 C9 C10 . . . . 178.91(17) ?
    C13 C8 C9 C10 . . . . -0.2(3) ?
    C8 C9 C10 C11 . . . . 1.8(3) ?
    C9 C10 C11 C12 . . . . -2.0(3) ?
    C9 C10 C11 C14 . . . . -179.97(18) ?
    C10 C11 C12 C13 . . . . 0.7(3) ?
    C14 C11 C12 C13 . . . . 178.65(18) ?
    C11 C12 C13 C8 . . . . 0.8(3) ?
    O1 C8 C13 C12 . . . . 179.74(17) ?
    C9 C8 C13 C12 . . . . -1.0(3) ?
    N2 N1 C14 C11 . . . . -175.46(16) ?
    C10 C11 C14 N1 . . . . -167.71(19) ?
    C12 C11 C14 N1 . . . . 14.4(3) ?
    N1 N2 C15 O2 . . . . 5.4(3) ?
    N1 N2 C15 C16 . . . . -175.67(16) ?
    O2 C15 C16 C17 . . . . -145.1(2) ?
    N2 C15 C16 C17 . . . . 35.9(3) ?
    O2 C15 C16 C20 . . . . 33.0(3) ?
    N2 C15 C16 C20 . . . . -145.97(19) ?
    C20 C16 C17 C18 . . . . -0.5(3) ?
    C15 C16 C17 C18 . . . . 177.6(2) ?
    C19 N3 C18 C17 . . . . -0.3(3) ?
    C16 C17 C18 N3 . . . . 0.7(4) ?
    C18 N3 C19 C20 . . . . -0.3(4) ?
    N3 C19 C20 C16 . . . . 0.5(4) ?
    C17 C16 C20 C19 . . . . 0.0(3) ?
    C15 C16 C20 C19 . . . . -178.28(19) ?
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
    N2 H2 O2 1_655 0.86 2.34 3.136(2) 153 yes
    C14 H14 O2 1_655 0.93 2.53 3.302(2) 141 yes
data_60910c
_journal_date_recd_electronic     2006-09-25
_journal_date_accepted     2006-10-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     11
_journal_page_first     o4928
_journal_page_last     o4929
_journal_paper_category     EO
_journal_coeditor_code     EZ2039
_publ_contact_author_name     "Zhao, Yan-Li"
_publ_contact_author_address
;
'College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
P. R. China'
;
_publ_contact_author_email     zhao_yanli@163.com
_publ_contact_author_fax     '086(022)23001002'
_publ_contact_author_phone     '086(022)60270087'
_publ_section_title
;
(E)-N'-(4-(2-Chlorobenzyloxy)benzylidene)isonicotinohydrazide
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    "Zhao, Yan-Li"
;
College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
People's Republic of China
;
    "Zhang, Qiao-Zhen"
;
College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
People's Republic of China
;
    "Chen, Xin"
;
College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
People's Republic of China
;
    "Yu, Ming"
;
College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
People's Republic of China
;
