##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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/  #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-02-24
_journal_date_accepted     2007-03-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     o2144
_journal_page_last     o2145
_journal_paper_category     EO
_journal_coeditor_code     LH2320
_publ_contact_author_name     'Doctor Zu-Pei Liang'
_publ_contact_author_address
;Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
P. R. China
;
_publ_contact_author_email     zupeiliang@yahoo.com.cn
_publ_contact_author_fax     '86536 794 2518'
_publ_contact_author_phone     '86536 794 2518'
_publ_section_title
;
(E)---N'-(5-Bromo-2-hydroxybenzylidene)furan-2-carbohydrazide
monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Tai, Xi-Shi' .
;
Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
People's Republic of China
;
    'Yin, Jie' .
;
Department of Chemistry and Chemical Engineering
Ningxia University
Yinchuan 750021
People's Republic of China
;
    'Hao, Ming-Yang' .
;
Clinical College of Weifang Medical University
Weifang 261060
People's Republic of China
;
    'Liang, Zu-Pei' .
;
Department of Chemistry and Chemical Engineering
Weifang University
Weifang 261061
People's Republic of China
;
data_I
_chemical_name_systematic
;
(E)-N'-(5-bromo-2-hydroxybenzylidene)furan-2-carbohydrazide monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H9 Br N2 O3, H2 O'
_chemical_formula_sum     'C12 H11 Br N2 O4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C12 H9 Br N2 O3, H2 O'
_chemical_formula_weight     327.13
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     4.8880(8)
_cell_length_b     12.495(2)
_cell_length_c     20.889(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1275.8(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2741
_cell_measurement_theta_min     2.54
_cell_measurement_theta_max     25.95
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.703
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     3.234
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1997)'
_exptl_absorpt_correction_T_min     0.541
_exptl_absorpt_correction_T_max     0.634
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6358
_diffrn_reflns_av_R_equivalents     0.0408
_diffrn_reflns_av_sigmaI/netI     0.0515
_diffrn_reflns_theta_min     1.90
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     24
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     .
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     .
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_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 > 2sigma(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     2238
_reflns_number_gt     1954
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0389
_refine_ls_R_factor_gt     0.0293
_refine_ls_wR_factor_gt     0.0654
_refine_ls_wR_factor_ref     0.0695
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.033
_refine_ls_number_reflns     2238
_refine_ls_number_parameters     174
_refine_ls_number_restraints     15
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0277P)²] 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     0.361
_refine_diff_density_min     -0.210
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0291(16)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 795 Friedel pairs'
_refine_ls_abs_structure_Flack     0.007(11)
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'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
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 1.41128(8) -0.14792(3) 0.98063(2) 0.05003(17) Uani d . 1 . .
    O O1 0.7552(6) 0.2278(2) 0.88643(12) 0.0511(7) Uani d . 1 . .
    H H1 0.6507 0.2109 0.8575 0.077 Uiso calc R 1 . .
    O O2 0.1747(5) 0.21596(19) 0.73398(14) 0.0495(7) Uani d . 1 . .
    O O3 -0.1923(6) 0.1312(2) 0.64777(14) 0.0615(8) Uani d . 1 . .
    N N1 0.5121(6) 0.0871(2) 0.80357(13) 0.0334(7) Uani d . 1 . .
    N N2 0.3298(5) 0.0499(2) 0.75851(14) 0.0337(7) Uani d . 1 . .
    H H2A 0.3203 -0.0176 0.7507 0.040 Uiso calc R 1 . .
    C C1 0.8979(7) 0.1406(3) 0.90580(15) 0.0356(7) Uani d . 1 . .
    C C2 1.0886(8) 0.1546(3) 0.95407(17) 0.0445(8) Uani d . 1 . .
    H H2 1.1144 0.2224 0.9715 0.053 Uiso calc R 1 . .
    C C3 1.2397(7) 0.0705(3) 0.97663(18) 0.0404(8) Uani d . 1 . .
    H H3 1.3663 0.0810 1.0093 0.049 Uiso calc R 1 . .
    C C4 1.2027(7) -0.0304(3) 0.95040(18) 0.0367(8) Uani d . 1 . .
    C C5 1.0162(7) -0.0465(3) 0.90293(17) 0.0362(9) Uani d . 1 . .
    H H5 0.9917 -0.1148 0.8862 0.043 Uiso calc R 1 . .
    C C6 0.8607(7) 0.0390(3) 0.87897(16) 0.0323(8) Uani d . 1 . .
    C C7 0.6598(7) 0.0159(3) 0.82990(16) 0.0351(9) Uani d . 1 . .
    H H7 0.6378 -0.0548 0.8170 0.042 Uiso calc R 1 . .
    C C8 0.1676(7) 0.1176(3) 0.72679(18) 0.0335(8) Uani d . 1 . .
    C C9 -0.0249(7) 0.0677(3) 0.68245(16) 0.0338(8) Uani d . 1 . .
    C C10 -0.0712(9) -0.0366(3) 0.6705(2) 0.0548(11) Uani d . 1 . .
    H H10 0.0143 -0.0960 0.6883 0.066 Uiso calc R 1 . .
    C C11 -0.2888(11) -0.0333(5) 0.6227(3) 0.0758(16) Uani d U 1 . .
    H H11 -0.3688 -0.0923 0.6030 0.091 Uiso calc R 1 . .
    C C12 -0.3509(9) 0.0651(5) 0.6124(2) 0.0707(14) Uani d U 1 . .
    H H12 -0.4867 0.0879 0.5843 0.085 Uiso calc R 1 . .
    O O4 0.3323(5) 0.82655(19) 0.75505(15) 0.0586(8) Uani d D 1 . .
    H H4A 0.1861 0.7896 0.7594 0.070 Uiso d RD 1 . .
    H H4B 0.4797 0.7956 0.7666 0.070 Uiso d RD 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 0.0437(2) 0.0460(2) 0.0604(3) -0.0003(2) -0.0092(2) 0.01499(19)
    O1 0.0588(17) 0.0379(15) 0.0565(18) 0.0076(14) -0.0135(15) -0.0044(13)
    O2 0.0410(16) 0.0263(13) 0.0812(19) 0.0029(11) -0.0137(14) -0.0038(12)
    O3 0.0524(17) 0.067(2) 0.0647(19) 0.0007(16) -0.0101(14) 0.0135(16)
    N1 0.0333(17) 0.0318(16) 0.0353(17) -0.0022(13) -0.0012(13) -0.0023(13)
    N2 0.0357(17) 0.0234(14) 0.0420(17) -0.0038(13) -0.0071(13) -0.0032(12)
    C1 0.0355(17) 0.0331(18) 0.0381(19) 0.000(2) 0.0005(16) -0.0007(16)
    C2 0.052(2) 0.0358(19) 0.0456(19) -0.007(2) -0.0062(19) -0.0080(17)
    C3 0.0359(18) 0.049(2) 0.037(2) -0.0075(17) -0.0073(19) 0.0026(18)
    C4 0.0298(17) 0.039(2) 0.041(2) -0.0030(16) 0.0006(16) 0.0067(17)
    C5 0.0344(19) 0.0317(19) 0.043(2) -0.0079(15) 0.0007(16) 0.0004(15)
    C6 0.0297(19) 0.0324(18) 0.035(2) -0.0049(16) 0.0064(15) 0.0026(14)
    C7 0.041(2) 0.0278(19) 0.036(2) -0.0035(16) 0.0010(16) -0.0025(15)
    C8 0.0254(19) 0.032(2) 0.043(2) 0.0011(14) 0.0029(15) 0.0016(15)
    C9 0.0295(18) 0.037(2) 0.0351(19) 0.0024(15) -0.0004(15) 0.0028(15)
    C10 0.046(2) 0.028(2) 0.091(3) -0.0015(19) -0.001(3) -0.0013(19)
    C11 0.061(3) 0.085(4) 0.082(4) -0.035(3) 0.015(3) -0.049(3)
    C12 0.050(3) 0.112(4) 0.050(3) -0.019(3) -0.014(2) 0.001(3)
    O4 0.0442(17) 0.0287(15) 0.103(2) -0.0017(12) -0.0168(15) 0.0056(13)
_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
    Br1 C4 . 1.895(4) ?
    O1 C1 . 1.356(4) ?
    O1 H1 . 0.8200 ?
    O2 C8 . 1.238(4) ?
    O3 C9 . 1.351(4) ?
    O3 C12 . 1.352(5) ?
    N1 C7 . 1.271(4) ?
    N1 N2 . 1.377(4) ?
    N2 C8 . 1.336(4) ?
    N2 H2A . 0.8600 ?
    C1 C2 . 1.384(5) ?
    C1 C6 . 1.400(5) ?
    C2 C3 . 1.368(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.387(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.362(5) ?
    C5 C6 . 1.403(5) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.448(5) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.460(5) ?
    C9 C10 . 1.346(5) ?
    C10 C11 . 1.460(7) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.285(8) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    O4 H4A . 0.8554 ?
    O4 H4B . 0.8526 ?
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    ? ? ? ? ? ?
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 H1 . . 109.5 ?
    C9 O3 C12 . . 106.4(4) ?
    C7 N1 N2 . . 115.3(3) ?
    C8 N2 N1 . . 120.6(3) ?
    C8 N2 H2A . . 119.7 ?
    N1 N2 H2A . . 119.7 ?
    O1 C1 C2 . . 117.5(3) ?
    O1 C1 C6 . . 122.9(3) ?
    C2 C1 C6 . . 119.6(3) ?
    C3 C2 C1 . . 121.2(3) ?
    C3 C2 H2 . . 119.4 ?
    C1 C2 H2 . . 119.4 ?
    C2 C3 C4 . . 119.5(3) ?
    C2 C3 H3 . . 120.3 ?
    C4 C3 H3 . . 120.3 ?
    C5 C4 C3 . . 120.6(3) ?
    C5 C4 Br1 . . 119.3(3) ?
    C3 C4 Br1 . . 120.2(3) ?
    C4 C5 C6 . . 120.7(3) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C1 C6 C5 . . 118.5(3) ?
    C1 C6 C7 . . 123.5(3) ?
    C5 C6 C7 . . 117.9(3) ?
    N1 C7 C6 . . 123.5(3) ?
    N1 C7 H7 . . 118.3 ?
    C6 C7 H7 . . 118.3 ?
    O2 C8 N2 . . 123.5(3) ?
    O2 C8 C9 . . 121.3(3) ?
    N2 C8 C9 . . 115.2(3) ?
    C10 C9 O3 . . 111.5(3) ?
    C10 C9 C8 . . 129.8(3) ?
    O3 C9 C8 . . 118.7(3) ?
    C9 C10 C11 . . 102.9(4) ?
    C9 C10 H10 . . 128.6 ?
    C11 C10 H10 . . 128.6 ?
    C12 C11 C10 . . 108.3(4) ?
    C12 C11 H11 . . 125.9 ?
    C10 C11 H11 . . 125.9 ?
    C11 C12 O3 . . 111.0(5) ?
    C11 C12 H12 . . 124.5 ?
    O3 C12 H12 . . 124.5 ?
    H4A O4 H4B . . 115.6 ?
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 . . . . -178.7(3) y
    O1 C1 C2 C3 . . . . 179.6(3) ?
    C6 C1 C2 C3 . . . . -0.7(6) ?
    C1 C2 C3 C4 . . . . 0.4(6) ?
    C2 C3 C4 C5 . . . . -0.5(6) ?
    C2 C3 C4 Br1 . . . . 179.7(3) ?
    C3 C4 C5 C6 . . . . 0.9(5) ?
    Br1 C4 C5 C6 . . . . -179.3(2) y
    O1 C1 C6 C5 . . . . -179.2(3) ?
    C2 C1 C6 C5 . . . . 1.1(5) ?
    O1 C1 C6 C7 . . . . -2.5(5) y
    C2 C1 C6 C7 . . . . 177.8(3) ?
    C4 C5 C6 C1 . . . . -1.2(5) ?
    C4 C5 C6 C7 . . . . -178.1(3) ?
    N2 N1 C7 C6 . . . . -179.1(3) y
    C1 C6 C7 N1 . . . . 5.0(5) y
    C5 C6 C7 N1 . . . . -178.2(3) y
    N1 N2 C8 O2 . . . . 2.2(5) y
    N1 N2 C8 C9 . . . . -177.3(3) y
    C12 O3 C9 C10 . . . . -0.1(4) y
    C12 O3 C9 C8 . . . . -178.6(3) y
    O2 C8 C9 C10 . . . . -176.6(4) y
    N2 C8 C9 C10 . . . . 2.9(6) y
    O2 C8 C9 O3 . . . . 1.7(5) y
    N2 C8 C9 O3 . . . . -178.8(3) y
    O3 C9 C10 C11 . . . . 0.7(5) ?
    C8 C9 C10 C11 . . . . 179.1(4) ?
    C9 C10 C11 C12 . . . . -1.2(5) ?
    C10 C11 C12 O3 . . . . 1.2(6) ?
    C9 O3 C12 C11 . . . . -0.8(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
    N2 H2A O4 1_545 0.86 1.95 2.792(3) 166
    O1 H1 N1 . 0.82 2.03 2.738(4) 145
    O4 H4A O2 3_556 0.86 1.99 2.847(3) 174
    O4 H4B O2 3_656 0.85 1.96 2.787(3) 163
    C7 H7 O4 1_545 0.93 2.47 3.257(4) 142
    C10 H10 O4 1_545 0.93 2.30 3.152(5) 152
