##############################################################################
###                                                                        ###
###        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 # 
# article from which it was obtained.                                        #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2008-10-22
_journal_date_accepted     2008-11-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     12
_journal_page_first     o2320
_journal_page_last     o2320
_journal_paper_category     QO
_journal_coeditor_code     AT2659
_publ_contact_author_name     'Fang-Fang Jian'
_publ_contact_author_address
;
New Materials and Function Coordination
Chemistry Laboratory
Qingdao University of Science and Technology,
Qingdao 266042,
People's Republic of China
;
_publ_contact_author_email     'ffjian2008@163.com'
_publ_contact_author_fax     '86-0536-8785802'
_publ_contact_author_phone     '86-0536-8785802'
_publ_section_title
;
N'-(4-Bromobenzylidene)isonicotinohydrazide
;
loop_
    _publ_author_name
    _publ_author_address
    'Li-Min Li'
;
  Microscale Science Institute,
  Weifang University,
  Weifang 261061,
  People's Republic of China
;
    'Fang-Fang Jian'
;
  Microscale Science Institute,
  Weifang University,
  Weifang 261061,
  People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N'-(4-Bromobenzylidene)isonicotinohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 Br N3 O'
_chemical_formula_sum     'C13 H10 Br N3 O'
_chemical_formula_iupac     'C13 H10 Br N3 O'
_chemical_formula_weight     304.15
_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     18.715(9)
_cell_length_b     6.517(3)
_cell_length_c     10.126(5)
_cell_angle_alpha     90.00
_cell_angle_beta     95.512(9)
_cell_angle_gamma     90.00
_cell_volume     1229.3(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2167
_cell_measurement_theta_min     3.31
_cell_measurement_theta_max     24.29
_cell_measurement_temperature     273(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.643
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     3.334
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_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     7721
_diffrn_reflns_av_R_equivalents     0.0335
_diffrn_reflns_av_sigmaI/netI     0.0459
_diffrn_reflns_theta_min     2.19
_diffrn_reflns_theta_max     28.37
_diffrn_reflns_theta_full     28.37
_diffrn_measured_fraction_theta_max     0.970
_diffrn_measured_fraction_theta_full     0.970
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     25
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_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 >
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     2992
_reflns_number_gt     1914
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0728
_refine_ls_R_factor_gt     0.0363
_refine_ls_wR_factor_gt     0.0831
_refine_ls_wR_factor_ref     0.0944
_refine_ls_goodness_of_fit_ref     1.006
_refine_ls_restrained_S_all     1.006
_refine_ls_number_reflns     2992
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0429P)²+0.1134P] 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     0.390
_refine_diff_density_min     -0.553
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0072(10)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (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 Br 0.038461(17) 0.64201(4) 0.85386(4) 0.08031(18) Uani d . 1 . .
    N N3 0.25010(10) 1.5120(3) 0.93706(17) 0.0390(4) Uani d . 1 . .
    N N2 0.29511(10) 1.6713(3) 0.90925(18) 0.0386(4) Uani d . 1 . .
    H H2A 0.3079 1.6847 0.8304 0.046 Uiso calc R 1 . .
    O O1 0.30311(10) 1.7983(3) 1.11880(16) 0.0529(4) Uani d . 1 . .
    C C7 0.10215(13) 0.8680(3) 0.8543(3) 0.0457(6) Uani d . 1 . .
    C C10 0.19040(12) 1.2072(3) 0.8503(2) 0.0369(5) Uani d . 1 . .
    N N1 0.46415(11) 2.2729(3) 0.8926(2) 0.0545(6) Uani d . 1 . .
    C C4 0.36913(11) 1.9665(3) 0.9610(2) 0.0349(5) Uani d . 1 . .
    C C13 0.31906(12) 1.8058(3) 1.0047(2) 0.0362(5) Uani d . 1 . .
    C C9 0.19163(13) 1.0539(4) 0.7549(2) 0.0446(6) Uani d . 1 . .
    H H9A 0.2229 1.0656 0.6893 0.054 Uiso calc R 1 . .
    C C12 0.23656(13) 1.3861(3) 0.8414(2) 0.0417(5) Uani d . 1 . .
    H H12A 0.2570 1.4094 0.7626 0.050 Uiso calc R 1 . .
    C C3 0.37459(13) 2.1531(3) 1.0273(2) 0.0448(6) Uani d . 1 . .
    H H3B 0.3471 2.1787 1.0972 0.054 Uiso calc R 1 . .
    C C5 0.41305(13) 1.9365(4) 0.8605(2) 0.0455(6) Uani d . 1 . .
    H H5A 0.4115 1.8140 0.8133 0.055 Uiso calc R 1 . .
    C C11 0.14423(13) 1.1841(4) 0.9499(2) 0.0438(6) Uani d . 1 . .
    H H11A 0.1429 1.2844 1.0150 0.053 Uiso calc R 1 . .
    C C8 0.14730(14) 0.8850(3) 0.7560(3) 0.0488(6) Uani d . 1 . .
    H H8A 0.1480 0.7843 0.6911 0.059 Uiso calc R 1 . .
    C C6 0.10088(13) 1.0151(4) 0.9526(2) 0.0473(6) Uani d . 1 . .
    H H6A 0.0708 0.9994 1.0199 0.057 Uiso calc R 1 . .
    C C2 0.42134(14) 2.3003(4) 0.9882(3) 0.0515(6) Uani d . 1 . .
    H H2B 0.4229 2.4263 1.0315 0.062 Uiso calc R 1 . .
    C C1 0.45933(14) 2.0919(4) 0.8314(3) 0.0552(7) Uani d . 1 . .
    H H1B 0.4891 2.0684 0.7646 0.066 Uiso calc R 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
    Br 0.0729(3) 0.04607(19) 0.1216(4) -0.01855(14) 0.0075(2) -0.00034(16)
    N3 0.0430(11) 0.0399(10) 0.0350(10) -0.0045(8) 0.0083(8) 0.0038(9)
    N2 0.0456(11) 0.0415(10) 0.0301(10) -0.0063(8) 0.0103(8) 0.0034(8)
    O1 0.0674(12) 0.0593(10) 0.0341(9) -0.0110(9) 0.0160(8) -0.0036(8)
    C7 0.0409(13) 0.0333(12) 0.0618(16) 0.0013(9) -0.0016(12) 0.0032(11)
    C10 0.0383(12) 0.0367(11) 0.0352(12) 0.0003(9) 0.0013(10) 0.0032(10)
    N1 0.0568(14) 0.0567(14) 0.0492(13) -0.0143(11) 0.0019(11) 0.0077(11)
    C4 0.0363(12) 0.0387(12) 0.0294(11) 0.0036(9) 0.0022(9) 0.0023(9)
    C13 0.0380(13) 0.0390(11) 0.0321(12) 0.0051(9) 0.0055(10) 0.0024(10)
    C9 0.0509(14) 0.0462(13) 0.0375(13) 0.0051(11) 0.0081(11) -0.0005(11)
    C12 0.0469(14) 0.0440(13) 0.0355(12) -0.0016(10) 0.0102(11) 0.0037(11)
    C3 0.0457(14) 0.0457(14) 0.0437(13) 0.0035(10) 0.0086(11) -0.0041(11)
    C5 0.0482(14) 0.0493(13) 0.0400(13) -0.0052(11) 0.0097(11) -0.0050(11)
    C11 0.0472(14) 0.0443(13) 0.0403(13) -0.0005(10) 0.0060(11) -0.0057(10)
    C8 0.0571(16) 0.0396(13) 0.0487(15) 0.0076(11) 0.0005(13) -0.0090(11)
    C6 0.0431(14) 0.0510(14) 0.0489(14) -0.0025(11) 0.0103(11) 0.0065(12)
    C2 0.0532(16) 0.0402(13) 0.0596(16) -0.0022(11) -0.0029(14) -0.0006(12)
    C1 0.0541(16) 0.0706(18) 0.0428(14) -0.0117(13) 0.0139(12) 0.0010(13)
_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
    Br C7 . 1.894(2) ?
    N3 C12 . 1.276(3) ?
    N3 N2 . 1.383(2) ?
    N2 C13 . 1.349(3) ?
    N2 H2A . 0.8600 ?
    O1 C13 . 1.222(3) ?
    C7 C8 . 1.371(4) ?
    C7 C6 . 1.384(3) ?
    C10 C9 . 1.391(3) ?
    C10 C11 . 1.398(3) ?
    C10 C12 . 1.459(3) ?
    N1 C2 . 1.326(3) ?
    N1 C1 . 1.331(3) ?
    C4 C5 . 1.382(3) ?
    C4 C3 . 1.388(3) ?
    C4 C13 . 1.500(3) ?
    C9 C8 . 1.379(3) ?
    C9 H9A . 0.9300 ?
    C12 H12A . 0.9300 ?
    C3 C2 . 1.382(3) ?
    C3 H3B . 0.9300 ?
    C5 C1 . 1.382(3) ?
    C5 H5A . 0.9300 ?
    C11 C6 . 1.370(3) ?
    C11 H11A . 0.9300 ?
    C8 H8A . 0.9300 ?
    C6 H6A . 0.9300 ?
    C2 H2B . 0.9300 ?
    C1 H1B . 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
    C12 N3 N2 . . 114.10(18) ?
    C13 N2 N3 . . 120.59(18) ?
    C13 N2 H2A . . 119.7 ?
    N3 N2 H2A . . 119.7 ?
    C8 C7 C6 . . 121.4(2) ?
    C8 C7 Br . . 119.52(19) ?
    C6 C7 Br . . 119.09(19) ?
    C9 C10 C11 . . 118.4(2) ?
    C9 C10 C12 . . 118.8(2) ?
    C11 C10 C12 . . 122.8(2) ?
    C2 N1 C1 . . 116.1(2) ?
    C5 C4 C3 . . 117.3(2) ?
    C5 C4 C13 . . 123.5(2) ?
    C3 C4 C13 . . 119.2(2) ?
    O1 C13 N2 . . 123.8(2) ?
    O1 C13 C4 . . 121.6(2) ?
    N2 C13 C4 . . 114.59(18) ?
    C8 C9 C10 . . 121.2(2) ?
    C8 C9 H9A . . 119.4 ?
    C10 C9 H9A . . 119.4 ?
    N3 C12 C10 . . 122.9(2) ?
    N3 C12 H12A . . 118.6 ?
    C10 C12 H12A . . 118.6 ?
    C4 C3 C2 . . 119.3(2) ?
    C4 C3 H3B . . 120.4 ?
    C2 C3 H3B . . 120.4 ?
    C4 C5 C1 . . 118.9(2) ?
    C4 C5 H5A . . 120.6 ?
    C1 C5 H5A . . 120.6 ?
    C6 C11 C10 . . 120.6(2) ?
    C6 C11 H11A . . 119.7 ?
    C10 C11 H11A . . 119.7 ?
    C7 C8 C9 . . 118.9(2) ?
    C7 C8 H8A . . 120.5 ?
    C9 C8 H8A . . 120.5 ?
    C11 C6 C7 . . 119.5(2) ?
    C11 C6 H6A . . 120.3 ?
    C7 C6 H6A . . 120.3 ?
    N1 C2 C3 . . 124.0(2) ?
    N1 C2 H2B . . 118.0 ?
    C3 C2 H2B . . 118.0 ?
    N1 C1 C5 . . 124.4(2) ?
    N1 C1 H1B . . 117.8 ?
    C5 C1 H1B . . 117.8 ?
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 H2A O1 4_595 0.86 2.14 2.966(3) 161 yes
    C12 H12A O1 4_595 0.93 2.60 3.377(3) 142 yes
