##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     'cif_core.dic'
_audit_conform_dict_version     2.2
_journal_date_recd_electronic     2002-12-20
_journal_date_accepted     2003-01-14
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2003
_journal_volume     59
_journal_issue      3
_journal_page_first     m73
_journal_page_last     m75
_journal_paper_category     FM
_publ_contact_author_name     'Dr Ljiljana Karanovic'
_publ_contact_author_address
;
Faculty of Mining and Geology
Laboratory of Crystallography
Djusina 7
11000 Belgrade
Yugoslavia
;
_publ_contact_author_email     'ljika2002@yahoo.com'
_publ_contact_author_fax     '381 11 635217'
_publ_contact_author_phone     '381 11 635217'
_publ_section_title
;
Dibromo(pyridoxal semicarbazone-κ³N¹,O³,O^3'^)copper(II)
;
loop_
    _publ_author_name
    _publ_author_address
    'Poleti, Dejan'
;
Department of General and Inorganic Chemistry
Faculty of Technology and Metallurgy
Karnegijeva 4
11000 Belgrade
Yugoslavia
;
    "Karanović, Ljiljana"
;
Faculty of Mining and Geology
Laboratory of Crystallography
Djušina 7
11000 Belgrade
Yugoslavia
;
    'Leovac, Vukadin M.'
;
Institute of Chemistry
Faculty of Natural Sciences
Trg Dositeja Obradovića 4
21000 Novi Sad
Yugoslavia
;
    "Jevtović, Violeta S."
;
Institute of Chemistry
Faculty of Natural Sciences
Trg Dositeja Obradovića 4
21000 Novi Sad
Yugoslavia
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Dibromo(pyridoxal semicarbazone-κ³N¹,O³,O^3'^)copper(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H12 Br2 Cu N4 O3'
_chemical_formula_sum     'C9 H12 Br2 Cu N4 O3'
_chemical_formula_iupac     '[Cu Br2 (C9 H12 N4 O3)]'
_chemical_formula_weight     447.59
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.5764(10)
_cell_length_b     8.7614(11)
_cell_length_c     10.8154(14)
_cell_angle_alpha     92.965(3)
_cell_angle_beta     97.881(2)
_cell_angle_gamma     108.709(3)
_cell_volume     670.05(15)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     769
_cell_measurement_theta_min     4.93
_cell_measurement_theta_max     56.71
_cell_measurement_temperature     298.0(10)
_exptl_crystal_description     plate
_exptl_crystal_colour     green
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     2.218
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     434
_exptl_absorpt_coefficient_mu     7.601
_exptl_absorpt_correction_type     empirical
_exptl_absorpt_process_details     '(XPREP in SHELXTL; Bruker, 1997)'
_exptl_absorpt_correction_T_min     0.291
_exptl_absorpt_correction_T_max     0.587
_exptl_special_details
;
Preliminary cell constants are calculated from 119 strong reflections
(120 frames, each 0.3° in ω). Final cell parameters are determined
using 769 reflections in a global refinement of data obtained after
integration of intensities. During data collection, five sets of
exposures in combination of ω and φ scans nominally covered over a
hemisphere of the reciprocal space. Each exposure was collected 20 s
and covered 0.25° in ω. The crystal-to-detector distance was 3.8 cm.
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Model CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     81.92
_diffrn_reflns_number     7646
_diffrn_reflns_av_R_equivalents     0.037
_diffrn_reflns_av_sigmaI/netI     0.067
_diffrn_reflns_theta_min     2.96
_diffrn_reflns_theta_max     30.49
_diffrn_reflns_theta_full     30.49
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     none
_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     4057
_reflns_number_gt     2678
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.061
_refine_ls_R_factor_gt     0.033
_refine_ls_wR_factor_gt     0.058
_refine_ls_wR_factor_ref     0.063
_refine_ls_goodness_of_fit_ref     0.852
_refine_ls_restrained_S_all     0.852
_refine_ls_number_reflns     4057
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0213P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.16
_refine_diff_density_min     -0.56
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.0016(3)
_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'
    'Cu' 'Cu' 0.3201 1.2651
                         '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-NT (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SHELXTL (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                             'ORTEX-8a (McArdle, 1995; Burnett & Johnson, 1996)'
_computing_publication_material     'SHELXL97 and PARST (Nardelli, 1983, 1995)'
loop_
    _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
    _atom_site_type_symbol
    Br1 1.06532(5) 0.76179(4) 0.71736(4) 0.04243(11) Uani d . 1 . . Br
    Br2 0.68362(5) 0.95380(4) 0.84096(3) 0.03304(10) Uani d . 1 . . Br
    Cu 0.73454(5) 0.72847(4) 0.68497(4) 0.02544(10) Uani d . 1 . . Cu
    O1 0.7549(3) 0.8643(2) 0.5434(2) 0.0292(5) Uani d . 1 . . O
    O2 0.6829(3) 0.5569(2) 0.7888(2) 0.0339(5) Uani d . 1 . . O
    O3 -0.1085(4) 0.3557(3) 0.6695(4) 0.0867(12) Uani d . 1 . . O
    H3O -0.0496 0.4293 0.7246 0.130 Uiso calc R 1 . . H
    N1 0.4704(3) 0.6393(2) 0.5941(2) 0.0223(5) Uani d . 1 . . N
    N2 0.4442(3) 0.7228(3) 0.4936(2) 0.0280(6) Uani d . 1 . . N
    H2N 0.3364 0.7016 0.4465 0.034 Uiso calc R 1 . . H
    N3 0.5843(4) 0.9275(3) 0.3789(3) 0.0325(6) Uani d . 1 . . N
    H3AN 0.6816 1.0025 0.3630 0.039 Uiso calc R 1 . . H
    H3BN 0.4761 0.9085 0.3329 0.039 Uiso calc R 1 . . H
    N4 0.3654(4) 0.2429(3) 0.9149(2) 0.0283(6) Uani d . 1 . . N
    H4N 0.3695 0.1848 0.9763 0.034 Uiso calc R 1 . . H
    C1 0.5263(4) 0.3524(3) 0.8985(3) 0.0238(6) Uani d . 1 . . C
    C2 0.5213(4) 0.4534(3) 0.7997(3) 0.0232(6) Uani d . 1 . . C
    C3 0.3467(4) 0.4293(3) 0.7224(3) 0.0218(6) Uani d . 1 . . C
    C4 0.1826(4) 0.3048(3) 0.7442(3) 0.0275(7) Uani d . 1 . . C
    C5 0.1973(4) 0.2158(3) 0.8434(3) 0.0317(7) Uani d . 1 . . C
    H5C 0.0906 0.1368 0.8610 0.038 Uiso calc R 1 . . H
    C6 0.7024(4) 0.3646(4) 0.9819(3) 0.0326(7) Uani d . 1 . . C
    H6AC 0.7670 0.4756 1.0146 0.049 Uiso calc R 1 . . H
    H6BC 0.7818 0.3265 0.9354 0.049 Uiso calc R 1 . . H
    H6CC 0.6729 0.2998 1.0500 0.049 Uiso calc R 1 . . H
    C7 -0.0058(5) 0.2559(4) 0.6541(4) 0.0379(8) Uani d . 1 . . C
    H71C 0.0192 0.2549 0.5686 0.045 Uiso calc R 1 . . H
    H72C -0.0806 0.1466 0.6663 0.045 Uiso calc R 1 . . H
    C8 0.3292(4) 0.5236(3) 0.6186(3) 0.0249(6) Uani d . 1 . . C
    H8C 0.2122 0.4999 0.5680 0.030 Uiso calc R 1 . . H
    C9 0.6012(4) 0.8416(3) 0.4739(3) 0.0237(6) Uani d . 1 . . C
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 0.02325(17) 0.0475(2) 0.0602(3) 0.01147(14) 0.01120(16) 0.02805(18)
    Br2 0.0451(2) 0.03091(16) 0.02657(18) 0.01427(13) 0.01006(14) 0.01159(13)
    Cu 0.02213(19) 0.02415(17) 0.0257(2) 0.00150(14) 0.00129(15) 0.01071(15)
    O1 0.0267(11) 0.0275(10) 0.0274(12) 0.0010(8) 0.0013(10) 0.0109(9)
    O2 0.0239(11) 0.0326(11) 0.0382(14) -0.0003(9) -0.0010(10) 0.0201(10)
    O3 0.0464(18) 0.0639(19) 0.137(3) 0.0231(15) -0.027(2) -0.026(2)
    N1 0.0249(12) 0.0187(11) 0.0225(14) 0.0057(9) 0.0032(10) 0.0081(10)
    N2 0.0252(13) 0.0275(12) 0.0290(15) 0.0062(10) -0.0015(11) 0.0159(11)
    N3 0.0339(15) 0.0317(13) 0.0330(16) 0.0094(11) 0.0071(12) 0.0185(12)
    N4 0.0356(15) 0.0283(12) 0.0221(14) 0.0092(11) 0.0073(12) 0.0142(11)
    C1 0.0296(16) 0.0204(13) 0.0205(16) 0.0070(11) 0.0034(13) 0.0033(12)
    C2 0.0239(15) 0.0199(13) 0.0234(16) 0.0033(11) 0.0054(12) 0.0032(12)
    C3 0.0243(15) 0.0177(12) 0.0228(16) 0.0049(10) 0.0051(12) 0.0063(11)
    C4 0.0245(15) 0.0239(14) 0.0321(19) 0.0047(12) 0.0040(14) 0.0068(13)
    C5 0.0270(17) 0.0295(15) 0.0352(19) 0.0018(12) 0.0082(14) 0.0141(14)
    C6 0.0346(18) 0.0327(16) 0.0294(18) 0.0116(13) -0.0013(14) 0.0075(14)
    C7 0.0308(18) 0.0288(16) 0.051(2) 0.0018(13) 0.0129(16) 0.0077(15)
    C8 0.0223(14) 0.0231(13) 0.0268(17) 0.0046(11) 0.0015(13) 0.0062(12)
    C9 0.0292(16) 0.0210(13) 0.0217(16) 0.0079(11) 0.0068(13) 0.0037(12)
_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 Cu . 2.4017(6) yes
    Br2 Cu . 2.6860(6) yes
    Cu O2 . 1.895(2) yes
    Cu O1 . 1.980(2) yes
    Cu N1 . 1.990(2) yes
    O1 C9 . 1.247(3) ?
    O2 C2 . 1.294(3) ?
    O3 C7 . 1.362(4) ?
    O3 H3O . 0.8200 ?
    N1 C8 . 1.286(3) ?
    N1 N2 . 1.368(3) ?
    N2 C9 . 1.358(3) ?
    N2 H2N . 0.8600 ?
    N3 C9 . 1.321(4) ?
    N3 H3AN . 0.8600 ?
    N3 H3BN . 0.8600 ?
    N4 C1 . 1.329(3) ?
    N4 C5 . 1.339(4) ?
    N4 H4N . 0.8600 ?
    C1 C2 . 1.426(4) ?
    C1 C6 . 1.474(4) ?
    C2 C3 . 1.411(4) ?
    C3 C4 . 1.424(4) ?
    C3 C8 . 1.444(4) ?
    C4 C5 . 1.372(4) ?
    C4 C7 . 1.534(5) ?
    C5 H5C . 0.9300 ?
    C6 H6AC . 0.9600 ?
    C6 H6BC . 0.9600 ?
    C6 H6CC . 0.9600 ?
    C7 H71C . 0.9700 ?
    C7 H72C . 0.9700 ?
    C8 H8C . 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
    O2 Cu O1 . . 165.90(9) yes
    O2 Cu N1 . . 89.77(9) yes
    O1 Cu N1 . . 80.23(9) yes
    O2 Cu Br1 . . 91.72(7) yes
    O1 Cu Br1 . . 93.06(6) yes
    N1 Cu Br1 . . 154.38(7) yes
    O2 Cu Br2 . . 97.85(7) yes
    O1 Cu Br2 . . 93.30(6) yes
    N1 Cu Br2 . . 97.30(7) yes
    Br1 Cu Br2 . . 107.81(2) yes
    C9 O1 Cu . . 113.6(2) ?
    C2 O2 Cu . . 128.5(2) ?
    C7 O3 H3O . . 109.5 ?
    C8 N1 N2 . . 118.9(2) ?
    C8 N1 Cu . . 129.9(2) ?
    N2 N1 Cu . . 111.2(2) ?
    C9 N2 N1 . . 114.9(2) ?
    C9 N2 H2N . . 122.6 ?
    N1 N2 H2N . . 122.6 ?
    C9 N3 H3AN . . 120.0 ?
    C9 N3 H3BN . . 120.0 ?
    H3AN N3 H3BN . . 120.0 ?
    C1 N4 C5 . . 125.1(3) ?
    C1 N4 H4N . . 117.4 ?
    C5 N4 H4N . . 117.4 ?
    N4 C1 C2 . . 118.3(3) ?
    N4 C1 C6 . . 119.2(3) ?
    C2 C1 C6 . . 122.6(3) ?
    O2 C2 C3 . . 126.6(3) ?
    O2 C2 C1 . . 115.0(3) ?
    C3 C2 C1 . . 118.4(2) ?
    C2 C3 C4 . . 119.4(3) ?
    C2 C3 C8 . . 122.2(2) ?
    C4 C3 C8 . . 118.4(3) ?
    C5 C4 C3 . . 118.8(3) ?
    C5 C4 C7 . . 118.4(3) ?
    C3 C4 C7 . . 122.5(3) ?
    N4 C5 C4 . . 119.9(3) ?
    N4 C5 H5C . . 120.1 ?
    C4 C5 H5C . . 120.1 ?
    C1 C6 H6AC . . 109.5 ?
    C1 C6 H6BC . . 109.5 ?
    H6AC C6 H6BC . . 109.5 ?
    C1 C6 H6CC . . 109.5 ?
    H6AC C6 H6CC . . 109.5 ?
    H6BC C6 H6CC . . 109.5 ?
    O3 C7 C4 . . 113.8(3) ?
    O3 C7 H71C . . 108.8 ?
    C4 C7 H71C . . 108.8 ?
    O3 C7 H72C . . 108.8 ?
    C4 C7 H72C . . 108.8 ?
    H71C C7 H72C . . 107.7 ?
    N1 C8 C3 . . 122.0(3) ?
    N1 C8 H8C . . 119.0 ?
    C3 C8 H8C . . 119.0 ?
    O1 C9 N3 . . 122.5(3) ?
    O1 C9 N2 . . 119.8(3) ?
    N3 C9 N2 . . 117.7(3) ?
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
    O3 H3O Br1 1_455 0.82 2.77 3.358(3) 130 yes
    N2 H2N O3 2_566 0.86 1.90 2.752(4) 174 yes
    N3 H3AN Br1 2_776 0.86 2.61 3.457(2) 170 yes
    N3 H3BN Br2 2_676 0.86 2.65 3.338(3) 138 yes
    N4 H4N Br2 2_667 0.86 2.39 3.226(3) 165 yes
