##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2008-09-21
_journal_date_accepted     2008-09-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     11
_journal_page_first     o2070
_journal_page_last     o2070
_journal_paper_category     QO
_journal_coeditor_code     SU2066
_publ_contact_author_name     'Xu-Ming Deng'
_publ_contact_author_address
;
College of Animal Science and Veterinary Medicine
Jilin University
Jilin 130062
People's Republic of China
;
_publ_contact_author_email     xumingdeng08@126.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
(E)-4-Bromo-N'-(2-hydroxy-1-naphthylmethylene)benzohydrazide
;
loop_
    _publ_author_name
    _publ_author_address
    'Yun-Peng Diao'
;
College of Animal Science and Veterinary Medicine
Jilin University
Jilin 130062
People's Republic of China
and
College of Pharmacy
Dalian Medical University
Dalian 116044
People's Republic of China
;
    'Qi-Hui Zhang'
;
School of Traditional Chinese Materia Medica
Shenyang Pharmaceutical University
Shenyang 110016
People's Republic of China
;
    'Da-Cheng Wang'
;
College of Animal Science and Veterinary Medicine
Jilin University
Jilin 130062
People's Republic of China
;
    'Xu-Ming Deng'
;
College of Animal Science and Veterinary Medicine
Jilin University
Jilin 130062
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-4-Bromo-N'-(2-hydroxy-1-naphthylmethylene)benzohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H13 Br N2 O2'
_chemical_formula_sum     'C18 H13 Br N2 O2'
_chemical_formula_iupac     'C18 H13 Br N2 O2'
_chemical_formula_weight     369.21
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x, -y, z+1/2'
_cell_length_a     6.185(2)
_cell_length_b     4.7638(19)
_cell_length_c     25.689(10)
_cell_angle_alpha     90.00
_cell_angle_beta     95.449(7)
_cell_angle_gamma     90.00
_cell_volume     753.5(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1589
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     24.5
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.627
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     372
_exptl_absorpt_coefficient_mu     2.739
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.4937
_exptl_absorpt_correction_T_max     0.5143
_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 CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5817
_diffrn_reflns_av_R_equivalents     0.0338
_diffrn_reflns_av_sigmaI/netI     0.0930
_diffrn_reflns_theta_min     1.59
_diffrn_reflns_theta_max     26.98
_diffrn_reflns_theta_full     26.98
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_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 >
σ(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     3119
_reflns_number_gt     2443
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0562
_refine_ls_R_factor_gt     0.0395
_refine_ls_wR_factor_gt     0.0910
_refine_ls_wR_factor_ref     0.1013
_refine_ls_goodness_of_fit_ref     0.903
_refine_ls_restrained_S_all     0.903
_refine_ls_number_reflns     3119
_refine_ls_number_parameters     212
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details     'calc w=1/[σ²(Fo²)+]'
_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     0.307
_refine_diff_density_min     -0.238
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1493 Friedel pairs'
_refine_ls_abs_structure_Flack     0.026(12)
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (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
    Br Br1 1.08310(11) 0.22527(11) 1.13545(4) 0.0685(2) Uani d . 1 . .
    O O1 0.2012(5) -0.3701(5) 0.99811(12) 0.0474(7) Uani d . 1 . .
    O O2 -0.3678(6) -0.2844(6) 0.91908(13) 0.0509(8) Uani d . 1 . .
    H H2 -0.2458 -0.2481 0.9327 0.076 Uiso calc R 1 . .
    N N1 0.1759(5) 0.0647(6) 0.96274(13) 0.0379(7) Uani d D 1 . .
    N N2 -0.0057(5) -0.0129(6) 0.93167(12) 0.0377(7) Uani d . 1 . .
    C C18 0.7851(7) 0.2520(7) 1.04481(17) 0.0407(9) Uani d . 1 . .
    H H18 0.8775 0.3902 1.0342 0.049 Uiso calc R 1 . .
    C C1 0.8295(7) 0.1191(9) 1.09188(16) 0.0433(9) Uani d . 1 . .
    C C2 0.6996(7) -0.0854(9) 1.10869(16) 0.0480(10) Uani d . 1 . .
    H H2A 0.7329 -0.1711 1.1410 0.058 Uiso calc R 1 . .
    C C3 0.5173(7) -0.1632(8) 1.07685(17) 0.0432(10) Uani d . 1 . .
    H H3 0.4282 -0.3052 1.0875 0.052 Uiso calc R 1 . .
    C C4 0.4659(6) -0.0328(7) 1.02954(15) 0.0340(8) Uani d . 1 . .
    C C5 0.6012(6) 0.1770(7) 1.01362(16) 0.0369(8) Uani d . 1 . .
    H H5 0.5673 0.2669 0.9818 0.044 Uiso calc R 1 . .
    C C6 0.2705(6) -0.1305(8) 0.99609(15) 0.0350(8) Uani d . 1 . .
    C C7 -0.0776(6) 0.1545(8) 0.89501(16) 0.0357(8) Uani d . 1 . .
    H H7 -0.0023 0.3190 0.8893 0.043 Uiso calc R 1 . .
    C C8 -0.2727(6) 0.0903(7) 0.86278(15) 0.0361(8) Uani d . 1 . .
    C C9 -0.4138(6) -0.1175(8) 0.87700(16) 0.0399(9) Uani d . 1 . .
    C C10 -0.6139(7) -0.1627(9) 0.8477(2) 0.0513(11) Uani d . 1 . .
    H H10 -0.7084 -0.2975 0.8587 0.062 Uiso calc R 1 . .
    C C11 -0.6716(6) -0.0146(9) 0.80394(19) 0.0527(11) Uani d . 1 . .
    H H11 -0.8065 -0.0462 0.7857 0.063 Uiso calc R 1 . .
    C C12 -0.5319(7) 0.1866(8) 0.78536(19) 0.0459(10) Uani d . 1 . .
    C C13 -0.5851(8) 0.3322(10) 0.7382(2) 0.0558(12) Uani d . 1 . .
    H H13 -0.7177 0.2963 0.7191 0.067 Uiso calc R 1 . .
    C C14 -0.4491(8) 0.5229(10) 0.71980(18) 0.0596(12) Uani d . 1 . .
    H H14 -0.4861 0.6156 0.6883 0.071 Uiso calc R 1 . .
    C C15 -0.2513(8) 0.5774(10) 0.74925(17) 0.0568(11) Uani d . 1 . .
    H H15 -0.1576 0.7101 0.7372 0.068 Uiso calc R 1 . .
    C C16 -0.1927(6) 0.4422(8) 0.79472(15) 0.0441(9) Uani d . 1 . .
    H H16 -0.0587 0.4806 0.8129 0.053 Uiso calc R 1 . .
    C C17 -0.3314(6) 0.2444(7) 0.81494(17) 0.0377(9) Uani d . 1 . .
    H H1 0.209(11) 0.245(4) 0.969(3) 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
    Br1 0.0451(2) 0.0994(4) 0.0583(3) -0.0070(3) -0.00903(17) -0.0151(3)
    O1 0.0489(17) 0.0246(13) 0.068(2) -0.0093(12) -0.0010(14) 0.0020(13)
    O2 0.055(2) 0.0432(16) 0.055(2) -0.0164(13) 0.0070(15) -0.0067(14)
    N1 0.0431(18) 0.0268(15) 0.0425(18) -0.0060(14) -0.0022(14) -0.0048(13)
    N2 0.0343(15) 0.0308(15) 0.0473(19) -0.0038(13) 0.0002(13) -0.0074(14)
    C18 0.036(2) 0.043(2) 0.044(2) -0.0092(17) 0.0070(17) -0.0058(17)
    C1 0.036(2) 0.047(2) 0.046(3) -0.0004(18) 0.0002(17) -0.0128(19)
    C2 0.050(2) 0.050(3) 0.042(2) 0.000(2) -0.0038(19) 0.0053(19)
    C3 0.044(2) 0.035(2) 0.051(3) -0.0049(17) 0.0040(19) 0.0034(17)
    C4 0.038(2) 0.0274(18) 0.037(2) -0.0041(15) 0.0040(15) -0.0030(15)
    C5 0.038(2) 0.0343(19) 0.038(2) -0.0062(15) 0.0045(16) -0.0027(15)
    C6 0.038(2) 0.0250(18) 0.043(2) -0.0006(16) 0.0105(17) -0.0058(16)
    C7 0.035(2) 0.0306(18) 0.041(2) -0.0062(15) 0.0040(16) -0.0041(16)
    C8 0.036(2) 0.0308(18) 0.041(2) -0.0011(16) 0.0023(16) -0.0111(16)
    C9 0.041(2) 0.035(2) 0.044(2) -0.0055(17) 0.0084(17) -0.0101(17)
    C10 0.038(2) 0.049(2) 0.068(3) -0.0138(19) 0.008(2) -0.015(2)
    C11 0.031(2) 0.060(3) 0.064(3) -0.0061(18) -0.0082(18) -0.023(2)
    C12 0.038(2) 0.044(2) 0.055(3) 0.0017(17) -0.0037(19) -0.0178(18)
    C13 0.049(3) 0.057(3) 0.057(3) 0.009(2) -0.013(2) -0.015(2)
    C14 0.067(3) 0.068(3) 0.043(3) 0.010(3) -0.003(2) -0.001(2)
    C15 0.059(3) 0.066(3) 0.046(3) -0.002(2) 0.008(2) -0.001(2)
    C16 0.038(2) 0.051(3) 0.044(2) -0.0058(18) 0.0023(17) -0.0005(19)
    C17 0.033(2) 0.036(2) 0.043(2) 0.0018(15) 0.0005(16) -0.0104(16)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Br1 C1 . 1.907(4) ?
    O1 C6 . 1.222(5) ?
    O2 C9 . 1.350(5) ?
    O2 H2 . 0.8200 ?
    N1 C6 . 1.359(5) ?
    N1 N2 . 1.366(4) ?
    N1 H1 . 0.89(3) ?
    N2 C7 . 1.281(5) ?
    C18 C1 . 1.369(6) ?
    C18 C5 . 1.375(6) ?
    C18 H18 . 0.9300 ?
    C1 C2 . 1.359(6) ?
    C2 C3 . 1.379(6) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.375(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.389(5) ?
    C4 C6 . 1.490(5) ?
    C5 H5 . 0.9300 ?
    C7 C8 . 1.430(5) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.391(5) ?
    C8 C17 . 1.448(6) ?
    C9 C10 . 1.403(6) ?
    C10 C11 . 1.346(7) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.404(6) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.407(7) ?
    C12 C17 . 1.419(6) ?
    C13 C14 . 1.354(7) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.400(7) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.353(6) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.406(6) ?
    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
    C9 O2 H2 . . 109.5 ?
    C6 N1 N2 . . 117.7(3) ?
    C6 N1 H1 . . 118(5) ?
    N2 N1 H1 . . 121(5) ?
    C7 N2 N1 . . 118.0(3) ?
    C1 C18 C5 . . 118.7(4) ?
    C1 C18 H18 . . 120.7 ?
    C5 C18 H18 . . 120.7 ?
    C2 C1 C18 . . 122.5(4) ?
    C2 C1 Br1 . . 118.8(3) ?
    C18 C1 Br1 . . 118.7(3) ?
    C1 C2 C3 . . 118.6(4) ?
    C1 C2 H2A . . 120.7 ?
    C3 C2 H2A . . 120.7 ?
    C4 C3 C2 . . 120.7(4) ?
    C4 C3 H3 . . 119.7 ?
    C2 C3 H3 . . 119.7 ?
    C3 C4 C5 . . 119.3(4) ?
    C3 C4 C6 . . 118.4(3) ?
    C5 C4 C6 . . 122.2(4) ?
    C18 C5 C4 . . 120.2(4) ?
    C18 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    O1 C6 N1 . . 122.3(3) ?
    O1 C6 C4 . . 122.4(3) ?
    N1 C6 C4 . . 115.3(3) ?
    N2 C7 C8 . . 120.5(3) ?
    N2 C7 H7 . . 119.8 ?
    C8 C7 H7 . . 119.8 ?
    C9 C8 C7 . . 121.1(4) ?
    C9 C8 C17 . . 118.1(3) ?
    C7 C8 C17 . . 120.8(3) ?
    O2 C9 C8 . . 122.7(4) ?
    O2 C9 C10 . . 116.6(4) ?
    C8 C9 C10 . . 120.8(4) ?
    C11 C10 C9 . . 121.2(4) ?
    C11 C10 H10 . . 119.4 ?
    C9 C10 H10 . . 119.4 ?
    C10 C11 C12 . . 121.3(4) ?
    C10 C11 H11 . . 119.4 ?
    C12 C11 H11 . . 119.4 ?
    C11 C12 C13 . . 121.9(4) ?
    C11 C12 C17 . . 119.0(4) ?
    C13 C12 C17 . . 119.1(4) ?
    C14 C13 C12 . . 121.9(4) ?
    C14 C13 H13 . . 119.0 ?
    C12 C13 H13 . . 119.0 ?
    C13 C14 C15 . . 118.4(4) ?
    C13 C14 H14 . . 120.8 ?
    C15 C14 H14 . . 120.8 ?
    C16 C15 C14 . . 121.8(5) ?
    C16 C15 H15 . . 119.1 ?
    C14 C15 H15 . . 119.1 ?
    C15 C16 C17 . . 121.0(4) ?
    C15 C16 H16 . . 119.5 ?
    C17 C16 H16 . . 119.5 ?
    C16 C17 C12 . . 117.7(4) ?
    C16 C17 C8 . . 122.7(4) ?
    C12 C17 C8 . . 119.5(4) ?
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 1_565 0.89(3) 1.99(3) 2.841(4) 160(6)
    O2 H2 N2 . 0.82 1.86 2.580(4) 145.4
