##############################################################################
###                                                                        ###
###        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     2008-09-03
_journal_date_accepted     2008-09-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     10
_journal_page_first     o2022
_journal_page_last     o2022
_journal_paper_category     QO
_journal_coeditor_code     BH2193
_publ_contact_author_name     'Guo-Biao Cao'
_publ_contact_author_address
;
Department of Chemistry
Ankang University
Ankang Shanxi 725000
People's Republic of China
;
_publ_contact_author_email     guobiao_cao@126.com
_publ_section_title
;
(<i>E</i>)-<i>N</i>'-(3,5-Dibromo-2-hydroxybenzylidene)-4-hydroxybenzohydrazide
monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    "Wang, Xiao-Ya"
;
Department of Biology
Ankang University
Ankang Shanxi 725000
People's Republic of China
;
    "Cao, Guo-Biao"
;
Department of Chemistry
Ankang University
Ankang Shanxi 725000
People's Republic of China
;
    "Yang, Tao"
;
Department of Chemistry
Ankang University
Ankang Shanxi 725000
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(<i>E</i>)-<i>N</i>'-(3,5-Dibromo-2-hydroxybenzylidene)-4-hydroxybenzohydrazide
monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H10 Br2 N2 O3, H2 O'
_chemical_formula_sum     'C14 H12 Br2 N2 O4'
_chemical_formula_iupac     'C14 H10 Br2 N2 O3, H2 O'
_chemical_formula_weight     432.08
_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     6.9840(16)
_cell_length_b     12.678(3)
_cell_length_c     17.722(4)
_cell_angle_alpha     90.00
_cell_angle_beta     96.999(4)
_cell_angle_gamma     90.00
_cell_volume     1557.4(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1545
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     24.9
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.23
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.843
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     848
_exptl_absorpt_coefficient_mu     5.223
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.30748
_exptl_absorpt_correction_T_max     0.31817
_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     \w
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12695
_diffrn_reflns_av_R_equivalents     0.0751
_diffrn_reflns_av_sigmaI/netI     0.0803
_diffrn_reflns_theta_min     1.98
_diffrn_reflns_theta_max     26.99
_diffrn_reflns_theta_full     26.99
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details     ?
_reflns_number_total     3366
_reflns_number_gt     2045
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0934
_refine_ls_R_factor_gt     0.0461
_refine_ls_wR_factor_gt     0.0907
_refine_ls_wR_factor_ref     0.1064
_refine_ls_goodness_of_fit_ref     0.995
_refine_ls_restrained_S_all     0.994
_refine_ls_number_reflns     3366
_refine_ls_number_parameters     210
_refine_ls_number_restraints     4
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^] 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     0.001
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.424
_refine_diff_density_min     -0.423
_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'
    '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, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_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 0.07183(8) 0.86697(4) -0.00493(3) 0.0601(2) Uani d . 1 . .
    Br Br2 0.05286(8) 0.71867(5) -0.30593(3) 0.0664(2) Uani d . 1 . .
    O O1 0.1871(5) 0.6446(2) 0.03203(16) 0.0405(7) Uani d . 1 . .
    H H1 0.2190 0.5834 0.0420 0.061 Uiso calc R 1 . .
    O O2 0.3386(4) 0.4075(2) 0.14777(16) 0.0426(8) Uani d . 1 . .
    O O3 0.5946(6) -0.0702(2) 0.20309(16) 0.0594(10) Uani d . 1 . .
    H H3 0.6086 -0.0733 0.2497 0.089 Uiso calc R 1 . .
    O O4 0.4571(5) 0.2539(3) 0.39995(18) 0.0494(8) Uani d D 1 . .
    N N1 0.2698(5) 0.4520(3) 0.00247(19) 0.0323(8) Uani d . 1 . .
    N N2 0.3257(5) 0.3529(3) 0.02714(19) 0.0336(8) Uani d D 1 . .
    C C1 0.1784(6) 0.5746(3) -0.0955(2) 0.0301(10) Uani d . 1 . .
    C C2 0.1564(6) 0.6572(3) -0.0440(2) 0.0336(10) Uani d . 1 . .
    C C3 0.1013(6) 0.7560(3) -0.0737(3) 0.0388(11) Uani d . 1 . .
    C C4 0.0691(6) 0.7749(4) -0.1503(3) 0.0422(11) Uani d . 1 . .
    H H4 0.0323 0.8414 -0.1687 0.051 Uiso calc R 1 . .
    C C5 0.0927(6) 0.6928(4) -0.1997(2) 0.0385(11) Uani d . 1 . .
    C C6 0.1470(6) 0.5942(4) -0.1731(2) 0.0398(11) Uani d . 1 . .
    H H6 0.1628 0.5401 -0.2073 0.048 Uiso calc R 1 . .
    C C7 0.2368(6) 0.4704(3) -0.0687(2) 0.0358(10) Uani d . 1 . .
    H H7 0.2504 0.4166 -0.1033 0.043 Uiso calc R 1 . .
    C C8 0.3580(6) 0.3355(3) 0.1033(2) 0.0311(10) Uani d . 1 . .
    C C9 0.4152(6) 0.2264(3) 0.1270(2) 0.0292(9) Uani d . 1 . .
    C C10 0.4475(7) 0.2041(3) 0.2037(2) 0.0430(12) Uani d . 1 . .
    H H10 0.4294 0.2573 0.2383 0.052 Uiso calc R 1 . .
    C C11 0.5056(7) 0.1059(3) 0.2311(2) 0.0438(12) Uani d . 1 . .
    H H11 0.5262 0.0933 0.2832 0.053 Uiso calc R 1 . .
    C C12 0.5325(7) 0.0275(3) 0.1807(2) 0.0385(11) Uani d . 1 . .
    C C13 0.4980(7) 0.0477(3) 0.1040(2) 0.0528(14) Uani d . 1 . .
    H H13 0.5146 -0.0059 0.0696 0.063 Uiso calc R 1 . .
    C C14 0.4397(7) 0.1452(3) 0.0773(2) 0.0462(12) Uani d . 1 . .
    H H14 0.4163 0.1569 0.0252 0.055 Uiso calc R 1 . .
    H H2 0.356(7) 0.307(3) -0.008(2) 0.080 Uiso d D 1 . .
    H H4A 0.436(6) 0.309(3) 0.373(3) 0.080 Uiso d D 1 . .
    H H4B 0.5787(19) 0.245(4) 0.408(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 0.0799(4) 0.0359(3) 0.0643(4) 0.0158(3) 0.0076(3) -0.0051(3)
    Br2 0.0707(4) 0.0883(5) 0.0380(3) 0.0029(3) -0.0022(2) 0.0233(3)
    O1 0.061(2) 0.0292(17) 0.0304(16) 0.0048(16) 0.0005(15) 0.0034(13)
    O2 0.066(2) 0.0267(16) 0.0348(17) 0.0075(15) 0.0035(15) -0.0053(14)
    O3 0.122(3) 0.0215(17) 0.0333(18) 0.0134(19) 0.003(2) 0.0046(14)
    O4 0.070(2) 0.041(2) 0.0359(18) -0.0058(18) 0.0031(17) 0.0069(15)
    N1 0.035(2) 0.026(2) 0.034(2) 0.0008(16) 0.0007(16) 0.0021(16)
    N2 0.046(2) 0.023(2) 0.031(2) 0.0049(17) 0.0024(17) 0.0037(15)
    C1 0.032(2) 0.032(2) 0.026(2) 0.0011(19) 0.0028(18) 0.0022(19)
    C2 0.032(2) 0.035(3) 0.033(2) 0.001(2) 0.0032(19) 0.004(2)
    C3 0.039(3) 0.030(2) 0.047(3) 0.004(2) 0.004(2) 0.001(2)
    C4 0.041(3) 0.035(3) 0.050(3) 0.006(2) 0.001(2) 0.016(2)
    C5 0.035(2) 0.049(3) 0.030(2) 0.000(2) 0.0011(19) 0.015(2)
    C6 0.042(3) 0.045(3) 0.032(2) 0.004(2) 0.001(2) 0.000(2)
    C7 0.043(3) 0.032(3) 0.032(2) 0.003(2) 0.002(2) -0.0007(19)
    C8 0.029(2) 0.029(2) 0.034(2) -0.0019(19) 0.0004(19) 0.000(2)
    C9 0.034(2) 0.023(2) 0.030(2) -0.0003(19) 0.0010(18) 0.0003(18)
    C10 0.067(3) 0.033(3) 0.030(2) 0.007(2) 0.006(2) -0.010(2)
    C11 0.073(3) 0.032(3) 0.026(2) 0.009(2) 0.006(2) 0.001(2)
    C12 0.064(3) 0.019(2) 0.033(3) 0.003(2) 0.009(2) 0.0036(19)
    C13 0.104(4) 0.025(3) 0.029(3) 0.014(3) 0.006(3) -0.008(2)
    C14 0.081(4) 0.030(3) 0.026(2) 0.009(3) 0.001(2) -0.001(2)
_geom_special_details     ?
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 C3 . 1.888(4) ?
    Br2 C5 . 1.897(4) ?
    O1 C2 . 1.348(5) ?
    O1 H1 . 0.8200 ?
    O2 C8 . 1.225(5) ?
    O3 C12 . 1.355(5) ?
    O3 H3 . 0.8200 ?
    O4 H4A . 0.847(10) ?
    O4 H4B . 0.851(10) ?
    N1 C7 . 1.275(5) ?
    N1 N2 . 1.371(4) ?
    N2 C8 . 1.359(5) ?
    N2 H2 . 0.898(10) ?
    C1 C6 . 1.387(5) ?
    C1 C2 . 1.411(6) ?
    C1 C7 . 1.446(6) ?
    C2 C3 . 1.395(6) ?
    C3 C4 . 1.371(6) ?
    C4 C5 . 1.382(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.374(6) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.486(5) ?
    C9 C14 . 1.379(5) ?
    C9 C10 . 1.379(6) ?
    C10 C11 . 1.380(6) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.365(6) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.375(6) ?
    C13 C14 . 1.368(6) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 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
    C2 O1 H1 . . 109.5 ?
    C12 O3 H3 . . 109.5 ?
    H4A O4 H4B . . 108(2) ?
    C7 N1 N2 . . 119.5(4) ?
    C8 N2 N1 . . 118.2(3) ?
    C8 N2 H2 . . 124(4) ?
    N1 N2 H2 . . 117(4) ?
    C6 C1 C2 . . 119.4(4) ?
    C6 C1 C7 . . 119.6(4) ?
    C2 C1 C7 . . 120.9(4) ?
    O1 C2 C3 . . 119.1(4) ?
    O1 C2 C1 . . 122.8(4) ?
    C3 C2 C1 . . 118.1(4) ?
    C4 C3 C2 . . 122.3(4) ?
    C4 C3 Br1 . . 119.5(3) ?
    C2 C3 Br1 . . 118.2(3) ?
    C3 C4 C5 . . 118.6(4) ?
    C3 C4 H4 . . 120.7 ?
    C5 C4 H4 . . 120.7 ?
    C6 C5 C4 . . 121.1(4) ?
    C6 C5 Br2 . . 120.0(4) ?
    C4 C5 Br2 . . 118.9(3) ?
    C5 C6 C1 . . 120.5(4) ?
    C5 C6 H6 . . 119.7 ?
    C1 C6 H6 . . 119.7 ?
    N1 C7 C1 . . 120.2(4) ?
    N1 C7 H7 . . 119.9 ?
    C1 C7 H7 . . 119.9 ?
    O2 C8 N2 . . 120.0(4) ?
    O2 C8 C9 . . 123.9(4) ?
    N2 C8 C9 . . 116.1(4) ?
    C14 C9 C10 . . 117.3(4) ?
    C14 C9 C8 . . 124.3(4) ?
    C10 C9 C8 . . 118.4(4) ?
    C9 C10 C11 . . 122.5(4) ?
    C9 C10 H10 . . 118.7 ?
    C11 C10 H10 . . 118.7 ?
    C12 C11 C10 . . 119.0(4) ?
    C12 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 120.5 ?
    O3 C12 C11 . . 122.6(4) ?
    O3 C12 C13 . . 118.1(4) ?
    C11 C12 C13 . . 119.3(4) ?
    C14 C13 C12 . . 121.3(4) ?
    C14 C13 H13 . . 119.4 ?
    C12 C13 H13 . . 119.4 ?
    C13 C14 C9 . . 120.6(4) ?
    C13 C14 H14 . . 119.7 ?
    C9 C14 H14 . . 119.7 ?
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 . 0.82 1.86 2.578(4) 145.7 yes
    O3 H3 O2 2_645 0.82 1.83 2.642(4) 173.1 yes
    O4 H4A O3 2_655 0.847(10) 2.038(14) 2.878(4) 171(5) yes
    O4 H4B O1 2_645 0.851(10) 2.24(3) 2.969(5) 144(4) yes
    N2 H2 O4 4_565 0.898(10) 2.01(2) 2.874(5) 162(5) yes