##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N'-[1-(5-Bromo-2-hydroxyphenyl)ethylidene]-3,4,5-
trihydroxybenzohydrazide dimethyl sulfoxide solvate trihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H13 Br N2 O5, C2 H6 O S, 3(H2 O)'
_chemical_formula_sum     'C17 H25 Br N2 O9 S'
_chemical_formula_iupac     'C15 H13 Br N2 O5, C2 H6 O S, 3H2 O'
_chemical_formula_weight     513.36
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     21.5690(15)
_cell_length_b     7.0302(4)
_cell_length_c     28.4771(18)
_cell_angle_alpha     90.00
_cell_angle_beta     103.061(2)
_cell_angle_gamma     90.00
_cell_volume     4206.4(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3053
_cell_measurement_theta_min     2.68
_cell_measurement_theta_max     27.88
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.03
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.621
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2112
_exptl_absorpt_coefficient_mu     2.106
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.6104
_exptl_absorpt_correction_T_max     0.9395
_exptl_special_details
;
;
_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 APEXII CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9543
_diffrn_reflns_av_R_equivalents     0.0295
_diffrn_reflns_av_sigmaI/netI     0.0351
_diffrn_reflns_theta_min     2.15
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -25
_diffrn_reflns_limit_h_max     25
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_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     3694
_reflns_number_gt     3052
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0419
_refine_ls_R_factor_gt     0.0287
_refine_ls_wR_factor_gt     0.0613
_refine_ls_wR_factor_ref     0.0655
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_restrained_S_all     1.019
_refine_ls_number_reflns     3694
_refine_ls_number_parameters     307
_refine_ls_number_restraints     11
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0311P)²+3.5353P] 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     0.336
_refine_diff_density_min     -0.296
_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'
    'S' 'S' 0.1246 0.1234
                         '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, 2010)'
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 0.525034(11) 1.15033(4) 1.066977(9) 0.01977(9) Uani d . 1 . .
    S S 0.15785(3) 0.18073(10) 0.73419(2) 0.02470(17) Uani d . 1 . .
    O O1 0.25101(8) 1.0736(3) 1.07882(6) 0.0201(4) Uani d D 1 . .
    H H1 0.2293(12) 1.052(4) 1.0519(7) 0.030 Uiso d D 1 . .
    O O2 0.78049(8) 0.7413(3) 0.83940(6) 0.0205(4) Uani d D 1 . .
    H H2A 0.7527(12) 0.791(4) 0.8174(8) 0.031 Uiso d D 1 . .
    H H2B 0.7763(14) 0.801(4) 0.8636(8) 0.031 Uiso d D 1 . .
    O O3 0.12345(8) 0.6895(3) 0.77600(6) 0.0193(4) Uani d D 1 . .
    H H3A 0.1436(13) 0.590(3) 0.7769(11) 0.029 Uiso d D 1 . .
    H H3B 0.1157(13) 0.721(4) 0.7481(7) 0.029 Uiso d D 1 . .
    O O4 0.19398(10) 0.9307(3) 0.84748(7) 0.0382(5) Uani d D 1 . .
    H H4A 0.2210(14) 1.012(4) 0.8408(12) 0.057 Uiso d D 1 . .
    H H4B 0.1779(16) 0.866(4) 0.8207(9) 0.057 Uiso d D 1 . .
    O O9 0.11275(8) 0.9528(3) 1.00576(6) 0.0188(4) Uani d . 1 . .
    O O10 0.18508(9) 0.3495(3) 0.76525(6) 0.0288(5) Uani d . 1 . .
    O O12 0.00733(8) 0.7056(3) 0.80056(6) 0.0302(5) Uani d D 1 . .
    H H12 0.0426(10) 0.702(5) 0.7930(11) 0.045 Uiso d D 1 . .
    O O13 -0.10287(8) 0.7412(3) 0.82391(6) 0.0210(4) Uani d D 1 . .
    H H13 -0.1337(11) 0.749(4) 0.8352(10) 0.032 Uiso d D 1 . .
    O O14 -0.11122(8) 0.8463(3) 0.91444(6) 0.0213(4) Uani d D 1 . .
    H H14 -0.1073(14) 0.900(4) 0.9405(7) 0.032 Uiso d D 1 . .
    N N1 0.22497(9) 0.9902(3) 0.99005(7) 0.0148(5) Uani d . 1 . .
    N N2 0.17589(9) 0.9350(3) 0.95289(7) 0.0146(5) Uani d D 1 . .
    H H2N 0.1813(11) 0.933(4) 0.9235(5) 0.018 Uiso d D 1 . .
    C C1 0.31207(11) 1.0888(4) 1.07379(8) 0.0156(5) Uani d . 1 . .
    C C2 0.35764(12) 1.1406(4) 1.11456(9) 0.0186(6) Uani d . 1 . .
    H H2 0.3452 1.1618 1.1441 0.022 Uiso calc R 1 . .
    C C3 0.42073(11) 1.1617(4) 1.11280(9) 0.0175(6) Uani d . 1 . .
    H H3 0.4516 1.1992 1.1407 0.021 Uiso calc R 1 . .
    C C4 0.43828(11) 1.1272(3) 1.06974(9) 0.0156(5) Uani d . 1 . .
    C C5 0.39418(11) 1.0743(3) 1.02900(9) 0.0150(5) Uani d . 1 . .
    H H5 0.4074 1.0523 0.9998 0.018 Uiso calc R 1 . .
    C C6 0.32987(11) 1.0524(3) 1.02996(8) 0.0135(5) Uani d . 1 . .
    C C7 0.28342(11) 0.9907(3) 0.98599(8) 0.0143(5) Uani d . 1 . .
    C C8 0.30638(12) 0.9305(4) 0.94239(9) 0.0199(6) Uani d . 1 . .
    H H8A 0.2713 0.8716 0.9190 0.030 Uiso calc R 1 . .
    H H8B 0.3411 0.8386 0.9519 0.030 Uiso calc R 1 . .
    H H8C 0.3218 1.0420 0.9278 0.030 Uiso calc R 1 . .
    C C9 0.11782(11) 0.9227(3) 0.96425(9) 0.0148(5) Uani d . 1 . .
    C C10 0.06185(11) 0.8702(3) 0.92563(8) 0.0131(5) Uani d . 1 . .
    C C11 0.06462(11) 0.8147(4) 0.87924(8) 0.0157(6) Uani d . 1 . .
    H H11 0.1045 0.8087 0.8703 0.019 Uiso calc R 1 . .
    C C12 0.00928(12) 0.7683(4) 0.84614(8) 0.0172(6) Uani d . 1 . .
    C C13 -0.04955(11) 0.7827(4) 0.85844(8) 0.0146(5) Uani d . 1 . .
    C C14 -0.05204(11) 0.8373(4) 0.90472(8) 0.0142(5) Uani d . 1 . .
    C C15 0.00347(11) 0.8764(3) 0.93839(9) 0.0145(5) Uani d . 1 . .
    H H15 0.0017 0.9078 0.9705 0.017 Uiso calc R 1 . .
    C C16 0.07421(15) 0.1949(6) 0.72909(17) 0.0685(13) Uani d . 1 . .
    H H16A 0.0645 0.1626 0.7601 0.103 Uiso calc R 1 . .
    H H16B 0.0525 0.1053 0.7044 0.103 Uiso calc R 1 . .
    H H16C 0.0596 0.3244 0.7199 0.103 Uiso calc R 1 . .
    C C17 0.15995(19) 0.2421(5) 0.67432(11) 0.0490(10) Uani d . 1 . .
    H H17A 0.1387 0.3648 0.6661 0.074 Uiso calc R 1 . .
    H H17B 0.1380 0.1441 0.6522 0.074 Uiso calc R 1 . .
    H H17C 0.2043 0.2514 0.6715 0.074 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
    Br C4 . 1.898(2) ?
    S O10 . 1.516(2) ?
    S C17 . 1.769(3) ?
    S C16 . 1.780(3) ?
    O1 C1 . 1.361(3) ?
    O1 H1 . 0.818(17) ?
    O2 H2A . 0.839(17) ?
    O2 H2B . 0.830(17) ?
    O3 H3A . 0.823(17) ?
    O3 H3B . 0.804(17) ?
    O4 H4A . 0.867(18) ?
    O4 H4B . 0.889(18) ?
    O9 C9 . 1.230(3) ?
    O12 C12 . 1.363(3) ?
    O12 H12 . 0.837(18) ?
    O13 C13 . 1.365(3) ?
    O13 H13 . 0.803(17) ?
    O14 C14 . 1.368(3) ?
    O14 H14 . 0.821(17) ?
    N1 C7 . 1.292(3) ?
    N1 N2 . 1.373(3) ?
    N2 C9 . 1.365(3) ?
    N2 H2N . 0.870(10) ?
    C1 C2 . 1.389(3) ?
    C1 C6 . 1.410(3) ?
    C2 C3 . 1.381(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.384(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.375(3) ?
    C5 C6 . 1.402(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.481(3) ?
    C7 C8 . 1.498(3) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 C10 . 1.484(3) ?
    C10 C15 . 1.388(3) ?
    C10 C11 . 1.391(3) ?
    C11 C12 . 1.383(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.394(3) ?
    C13 C14 . 1.385(3) ?
    C14 C15 . 1.382(3) ?
    C15 H15 . 0.9500 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
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
    O10 S C17 . . 106.27(14) ?
    O10 S C16 . . 104.83(14) ?
    C17 S C16 . . 98.9(2) ?
    C1 O1 H1 . . 106(2) ?
    H2A O2 H2B . . 103(3) ?
    H3A O3 H3B . . 105(3) ?
    H4A O4 H4B . . 107(3) ?
    C12 O12 H12 . . 115(2) ?
    C13 O13 H13 . . 110(2) ?
    C14 O14 H14 . . 107(2) ?
    C7 N1 N2 . . 122.0(2) ?
    C9 N2 N1 . . 115.11(19) ?
    C9 N2 H2N . . 123.8(17) ?
    N1 N2 H2N . . 119.9(17) ?
    O1 C1 C2 . . 116.8(2) ?
    O1 C1 C6 . . 122.9(2) ?
    C2 C1 C6 . . 120.3(2) ?
    C3 C2 C1 . . 121.0(2) ?
    C3 C2 H2 . . 119.5 ?
    C1 C2 H2 . . 119.5 ?
    C2 C3 C4 . . 118.8(2) ?
    C2 C3 H3 . . 120.6 ?
    C4 C3 H3 . . 120.6 ?
    C5 C4 C3 . . 121.3(2) ?
    C5 C4 Br . . 119.25(18) ?
    C3 C4 Br . . 119.44(18) ?
    C4 C5 C6 . . 120.8(2) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C5 C6 C1 . . 117.8(2) ?
    C5 C6 C7 . . 119.9(2) ?
    C1 C6 C7 . . 122.3(2) ?
    N1 C7 C6 . . 114.4(2) ?
    N1 C7 C8 . . 125.8(2) ?
    C6 C7 C8 . . 119.8(2) ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    O9 C9 N2 . . 120.2(2) ?
    O9 C9 C10 . . 121.4(2) ?
    N2 C9 C10 . . 118.4(2) ?
    C15 C10 C11 . . 119.6(2) ?
    C15 C10 C9 . . 115.6(2) ?
    C11 C10 C9 . . 124.8(2) ?
    C12 C11 C10 . . 119.8(2) ?
    C12 C11 H11 . . 120.1 ?
    C10 C11 H11 . . 120.1 ?
    O12 C12 C11 . . 124.2(2) ?
    O12 C12 C13 . . 115.4(2) ?
    C11 C12 C13 . . 120.4(2) ?
    O13 C13 C14 . . 122.5(2) ?
    O13 C13 C12 . . 118.0(2) ?
    C14 C13 C12 . . 119.5(2) ?
    O14 C14 C15 . . 123.5(2) ?
    O14 C14 C13 . . 116.4(2) ?
    C15 C14 C13 . . 120.1(2) ?
    C14 C15 C10 . . 120.5(2) ?
    C14 C15 H15 . . 119.8 ?
    C10 C15 H15 . . 119.8 ?
    S C16 H16A . . 109.5 ?
    S C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    S C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    S C17 H17A . . 109.5 ?
    S C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    S C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
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
    O1 H1 N1 . 0.818(17) 1.80(2) 2.531(3) 149(3)
    O1 H1 O9 . 0.818(17) 2.65(2) 3.338(2) 142(3)
    O2 H2A O10 3 0.839(17) 1.877(18) 2.703(2) 168(3)
    O2 H2A S 3 0.839(17) 2.86(2) 3.5458(19) 140(2)
    O2 H2B O1 5_677 0.830(17) 2.060(18) 2.880(2) 169(3)
    O3 H3A O10 . 0.823(17) 1.973(18) 2.785(3) 169(3)
    O3 H3B O13 2_556 0.804(17) 2.012(18) 2.802(2) 168(3)
    O4 H4A O2 3_455 0.867(18) 2.07(2) 2.915(3) 166(3)
    O4 H4B O3 . 0.889(18) 1.96(2) 2.817(3) 160(3)
    O12 H12 O3 . 0.837(18) 1.913(18) 2.751(2) 179(3)
    O13 H13 O2 1_455 0.803(17) 1.883(19) 2.651(2) 160(3)
    O13 H13 O14 . 0.803(17) 2.30(3) 2.727(2) 114(2)
    O14 H14 O9 5_577 0.821(17) 1.871(18) 2.682(2) 169(3)
    N2 H2N O4 . 0.870(10) 2.243(10) 3.113(3) 179(3)
data_global
_journal_date_recd_electronic     2010-02-10
_journal_date_accepted     2010-02-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      3
_journal_page_first     o721
_journal_page_last     o721
_journal_paper_category     QO
_journal_coeditor_code     HG2645
_publ_contact_author_name     'Hamid Khaledi'
_publ_contact_author_address
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email     'khaledi@perdana.um.edu.my'
_publ_contact_author_fax     '+60379674193'
_publ_contact_author_phone     '+60129195486'
_publ_section_title
;
N'-[1-(5-Bromo-2-hydroxyphenyl)ethylidene]-3,4,5-trihydroxybenzohydrazide
dimethyl sulfoxide solvate trihydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Suleiman Gwaram, Nura' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
    'Khaledi, Hamid' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
    'Mohd Ali, Hapipah' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
    'Robinson, Ward T.' .
;
Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
;
    'Abdulla, Mahmood A.' .
;
Department of Molecular Medicine, University of Malaya, 50603 Kuala Lumpur,
Malaysia
;
