##############################################################################
###                                                                        ###
###        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     SHELXL-97
_journal_date_recd_electronic     2008-07-16
_journal_date_accepted     2008-07-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1584
_journal_page_last     o1584
_journal_paper_category     QO
_journal_coeditor_code     BT2751
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
N'-(5-Bromo-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide
dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Alhadi, Abeer A.'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    'Ali, Hapipah M.'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    'Puvaneswary, Subramaniam'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    'Robinson, Ward T.'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N'-(5-Bromo-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide
dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 Br N2 O5, 2H2 O'
_chemical_formula_sum     'C14 H15 Br N2 O7'
_chemical_formula_weight     403.19
_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     30.8424(8)
_cell_length_b     3.79990(10)
_cell_length_c     12.8484(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.280(2)
_cell_angle_gamma     90.00
_cell_volume     1505.79(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2758
_cell_measurement_theta_min     3.2
_cell_measurement_theta_max     27.4
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Needle
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.03
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.779
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     816
_exptl_absorpt_coefficient_mu     2.773
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.658
_exptl_absorpt_correction_T_max     0.921
_diffrn_ambient_temperature     100(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'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9964
_diffrn_reflns_av_R_equivalents     0.0391
_diffrn_reflns_av_sigmaI/netI     0.0461
_diffrn_reflns_theta_min     1.32
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -38
_diffrn_reflns_limit_h_max     40
_diffrn_reflns_limit_k_min     -4
_diffrn_reflns_limit_k_max     4
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3424
_reflns_number_gt     2914
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0786
_refine_ls_R_factor_gt     0.0644
_refine_ls_wR_factor_gt     0.1441
_refine_ls_wR_factor_ref     0.1547
_refine_ls_goodness_of_fit_ref     1.222
_refine_ls_restrained_S_all     1.220
_refine_ls_number_reflns     3424
_refine_ls_number_parameters     241
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w=1/[σ²(Fo²)+(0.0499P)²+10.2476P] 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     1.084
_refine_diff_density_min     -1.822
_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     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 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 0.467910(16) 0.31017(16) 0.89799(4) 0.01787(17) Uani d . 1 . .
    O O1 0.32358(12) 0.6446(12) 0.5944(3) 0.0201(9) Uani d D 1 . .
    H H1O 0.3020(15) 0.745(18) 0.621(5) 0.030 Uiso d D 1 . .
    O O2 0.20078(11) 0.9755(11) 0.6545(3) 0.0182(8) Uani d . 1 . .
    O O3 0.05472(13) 1.3768(13) 0.7962(4) 0.0295(11) Uani d D 1 . .
    H H3O 0.0335(16) 1.36(2) 0.836(5) 0.044 Uiso d D 1 . .
    O O4 0.05208(14) 1.1036(15) 0.9894(4) 0.0353(12) Uani d D 1 . .
    H H4O 0.048(3) 0.933(15) 1.030(6) 0.053 Uiso d D 1 . .
    O O5 0.12324(12) 0.7692(12) 1.0737(3) 0.0182(9) Uani d D 1 . .
    H H5O 0.1471(12) 0.682(18) 1.092(5) 0.027 Uiso d D 1 . .
    O O1W 0.25912(12) 1.3152(13) 0.9988(3) 0.0209(9) Uani d D 1 . .
    H H1W1 0.2444(17) 1.382(18) 1.050(3) 0.031 Uiso d D 1 . .
    H H1W2 0.2806(14) 1.199(17) 1.020(4) 0.031 Uiso d D 1 . .
    O O2W -0.02887(15) 1.3435(17) 0.8657(5) 0.0506(16) Uani d D 1 . .
    H H2W1 -0.042(3) 1.30(2) 0.810(4) 0.076 Uiso d D 1 . .
    H H2W2 -0.038(3) 1.534(14) 0.890(7) 0.076 Uiso d D 1 . .
    N N1 0.27850(13) 0.8683(12) 0.7531(3) 0.0139(9) Uani d . 1 . .
    N N2 0.24174(13) 0.9859(13) 0.8027(3) 0.0138(9) Uani d . 1 . .
    H H2N 0.2431 1.0511 0.8684 0.017 Uiso calc R 1 . .
    C C1 0.35563(16) 0.5778(15) 0.6648(4) 0.0144(10) Uani d . 1 . .
    C C2 0.39381(16) 0.4251(16) 0.6295(4) 0.0173(11) Uani d . 1 . .
    H H2 0.3970 0.3730 0.5576 0.021 Uiso calc R 1 . .
    C C3 0.42746(17) 0.3479(16) 0.6985(4) 0.0193(12) Uani d . 1 . .
    H H3 0.4535 0.2431 0.6743 0.023 Uiso calc R 1 . .
    C C4 0.42245(16) 0.4256(16) 0.8025(4) 0.0160(11) Uani d . 1 . .
    C C5 0.38470(16) 0.5781(15) 0.8398(4) 0.0143(10) Uani d . 1 . .
    H H5 0.3820 0.6294 0.9118 0.017 Uiso calc R 1 . .
    C C6 0.35065(15) 0.6562(15) 0.7712(4) 0.0126(10) Uani d . 1 . .
    C C7 0.31105(16) 0.7988(15) 0.8138(4) 0.0130(10) Uani d . 1 . .
    H H7 0.3089 0.8415 0.8865 0.016 Uiso calc R 1 . .
    C C8 0.20343(16) 1.0010(13) 0.7503(4) 0.0108(10) Uani d . 1 . .
    C C9 0.16507(16) 1.0460(15) 0.8180(4) 0.0130(10) Uani d . 1 . .
    C C10 0.12793(16) 1.2046(16) 0.7771(4) 0.0163(11) Uani d . 1 . .
    H H10 0.1281 1.2984 0.7086 0.020 Uiso calc R 1 . .
    C C11 0.09101(17) 1.2242(15) 0.8368(4) 0.0176(12) Uani d . 1 . .
    C C12 0.09010(17) 1.0775(17) 0.9364(4) 0.0204(12) Uani d . 1 . .
    C C13 0.12713(17) 0.9146(15) 0.9777(4) 0.0152(11) Uani d . 1 . .
    C C14 0.16479(17) 0.9040(15) 0.9188(4) 0.0149(11) Uani d . 1 . .
    H H14 0.1903 0.8006 0.9468 0.018 Uiso calc R 1 . .
_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 C4 . 1.909(5) ?
    O1 C1 . 1.361(6) ?
    O1 H1O . 0.840(10) ?
    O2 C8 . 1.236(6) ?
    O3 C11 . 1.362(6) ?
    O3 H3O . 0.838(10) ?
    O4 C12 . 1.362(7) ?
    O4 H4O . 0.840(10) ?
    O5 C13 . 1.357(7) ?
    O5 H5O . 0.841(10) ?
    O1W H1W1 . 0.839(10) ?
    O1W H1W2 . 0.838(10) ?
    O2W H2W1 . 0.838(10) ?
    O2W H2W2 . 0.839(10) ?
    N1 C7 . 1.296(7) ?
    N1 N2 . 1.378(6) ?
    N2 C8 . 1.359(6) ?
    N2 H2N . 0.8800 ?
    C1 C2 . 1.391(7) ?
    C1 C6 . 1.408(7) ?
    C2 C3 . 1.393(8) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.378(8) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.388(7) ?
    C5 C6 . 1.400(7) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.446(7) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.482(7) ?
    C9 C10 . 1.395(7) ?
    C9 C14 . 1.403(7) ?
    C10 C11 . 1.378(7) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.396(8) ?
    C12 C13 . 1.401(8) ?
    C13 C14 . 1.390(7) ?
    C14 H14 . 0.9500 ?
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 H1O . . 113(5) ?
    C11 O3 H3O . . 111(6) ?
    C12 O4 H4O . . 112(6) ?
    C13 O5 H5O . . 110(5) ?
    H1W1 O1W H1W2 . . 109.6(18) ?
    H2W1 O2W H2W2 . . 109.5(18) ?
    C7 N1 N2 . . 115.1(4) ?
    C8 N2 N1 . . 120.0(4) ?
    C8 N2 H2N . . 120.0 ?
    N1 N2 H2N . . 120.0 ?
    O1 C1 C2 . . 118.3(5) ?
    O1 C1 C6 . . 121.6(5) ?
    C2 C1 C6 . . 120.1(5) ?
    C1 C2 C3 . . 120.6(5) ?
    C1 C2 H2 . . 119.7 ?
    C3 C2 H2 . . 119.7 ?
    C4 C3 C2 . . 119.1(5) ?
    C4 C3 H3 . . 120.5 ?
    C2 C3 H3 . . 120.5 ?
    C3 C4 C5 . . 121.5(5) ?
    C3 C4 Br1 . . 119.2(4) ?
    C5 C4 Br1 . . 119.3(4) ?
    C4 C5 C6 . . 120.0(5) ?
    C4 C5 H5 . . 120.0 ?
    C6 C5 H5 . . 120.0 ?
    C5 C6 C1 . . 118.7(5) ?
    C5 C6 C7 . . 118.3(4) ?
    C1 C6 C7 . . 122.9(5) ?
    N1 C7 C6 . . 120.1(4) ?
    N1 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    O2 C8 N2 . . 122.9(4) ?
    O2 C8 C9 . . 123.0(4) ?
    N2 C8 C9 . . 114.1(4) ?
    C10 C9 C14 . . 120.3(5) ?
    C10 C9 C8 . . 119.0(5) ?
    C14 C9 C8 . . 120.4(5) ?
    C11 C10 C9 . . 119.5(5) ?
    C11 C10 H10 . . 120.2 ?
    C9 C10 H10 . . 120.2 ?
    O3 C11 C10 . . 119.3(5) ?
    O3 C11 C12 . . 120.1(5) ?
    C10 C11 C12 . . 120.6(5) ?
    O4 C12 C11 . . 116.7(5) ?
    O4 C12 C13 . . 123.0(5) ?
    C11 C12 C13 . . 120.3(5) ?
    O5 C13 C14 . . 124.1(5) ?
    O5 C13 C12 . . 116.7(5) ?
    C14 C13 C12 . . 119.2(5) ?
    C13 C14 C9 . . 120.0(5) ?
    C13 C14 H14 . . 120.0 ?
    C9 C14 H14 . . 120.0 ?
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 C8 . . . . -167.2(5) ?
    O1 C1 C2 C3 . . . . -179.3(5) ?
    C6 C1 C2 C3 . . . . 0.1(9) ?
    C1 C2 C3 C4 . . . . -0.1(9) ?
    C2 C3 C4 C5 . . . . 0.1(9) ?
    C2 C3 C4 Br1 . . . . 178.5(4) ?
    C3 C4 C5 C6 . . . . 0.0(9) ?
    Br1 C4 C5 C6 . . . . -178.4(4) ?
    C4 C5 C6 C1 . . . . -0.1(8) ?
    C4 C5 C6 C7 . . . . 177.0(5) ?
    O1 C1 C6 C5 . . . . 179.4(5) ?
    C2 C1 C6 C5 . . . . 0.1(8) ?
    O1 C1 C6 C7 . . . . 2.5(9) ?
    C2 C1 C6 C7 . . . . -176.9(5) ?
    N2 N1 C7 C6 . . . . 176.8(5) ?
    C5 C6 C7 N1 . . . . -178.7(5) ?
    C1 C6 C7 N1 . . . . -1.8(8) ?
    N1 N2 C8 O2 . . . . -13.6(8) ?
    N1 N2 C8 C9 . . . . 165.7(5) ?
    O2 C8 C9 C10 . . . . -26.7(8) ?
    N2 C8 C9 C10 . . . . 154.0(5) ?
    O2 C8 C9 C14 . . . . 147.8(5) ?
    N2 C8 C9 C14 . . . . -31.4(7) ?
    C14 C9 C10 C11 . . . . 0.6(9) ?
    C8 C9 C10 C11 . . . . 175.2(5) ?
    C9 C10 C11 O3 . . . . -179.5(5) ?
    C9 C10 C11 C12 . . . . -2.0(9) ?
    O3 C11 C12 O4 . . . . -1.4(8) ?
    C10 C11 C12 O4 . . . . -178.9(6) ?
    O3 C11 C12 C13 . . . . 178.9(5) ?
    C10 C11 C12 C13 . . . . 1.4(9) ?
    O4 C12 C13 O5 . . . . 2.2(9) ?
    C11 C12 C13 O5 . . . . -178.1(5) ?
    O4 C12 C13 C14 . . . . -179.1(6) ?
    C11 C12 C13 C14 . . . . 0.6(9) ?
    O5 C13 C14 C9 . . . . 176.7(5) ?
    C12 C13 C14 C9 . . . . -1.9(8) ?
    C10 C9 C14 C13 . . . . 1.3(8) ?
    C8 C9 C14 C13 . . . . -173.2(5) ?
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 H1o N1 . 0.840(10)
                        1.91(5) 2.616(6) 141(7) yes
    O3 H3o O2w . 0.840(10)
                         1.96(4) 2.736(6) 153(7) yes
    O4 H4o O2w 3_577 0.840(10)
                             1.81(3) 2.623(8) 163(9) yes
    O5 H5o O2 4_576 0.840(10)
                            1.93(2) 2.764(5) 171(7) yes
    O1w H1w1 O2 4_586 0.840(10)
                              1.98(2) 2.812(5) 170(6) yes
    O1w H1w2 O1 4_576 0.840(10)
                              2.09(2) 2.914(6) 167(6) yes
    O2w H2w1 O3 2_546 0.840(10)
                              2.13(5) 2.845(9) 142(8) yes
    O2w H2w2 O4 3_587 0.840(10)
                              2.12(4) 2.900(8) 154(8) yes
