##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-06-10
_journal_date_accepted     2012-06-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      7
_journal_page_first     o2270
_journal_page_last     o2271
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812028863
_journal_coeditor_code     SU2461
_publ_contact_author_name     'Prof. Tahir, Muhammad Nawaz '
_publ_contact_author_address
;
Department of Physics
University of Sargodha
Punjab, Pakistan
;
_publ_contact_author_email     'dmntahir_uos@yahoo.com, zsrkk@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
4,6-Dibromo-2-[(<i>E</i>)-(4-{[(<i>E</i>)-3,5-dibromo-2-hydroxybenzylidene]\
amino}butyl)iminomethyl]phenol
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kargar, Hadi' .
;
Department of Chemistry,
Payame Noor University,
PO Box 19395-3697 Tehran,
I. R. of Iran
;
    'Kia, Reza'
;
Present address:
Structural Dynamics of (Bio)Chemical Systems,
Max Planck Institute for Biophysical Chemistry,
Am Fassberg 11,
37077 G\"ottingen,
Germany.
;
;
      Department of Chemistry,
      Science and Research Branch,
      Islamic Azad University,
      Tehran,
      Iran
;
    'Adabi Ardakani, Amir' .
;
Department of Chemistry,
Payame Noor University,
PO Box 19395-3697 Tehran,
I. R. of Iran
;
    'Tahir, Muhammad Nawaz' .
;
Department of Physics
University of Sargodha
Punjab, Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4,6-Dibromo-2-[(<i>E</i>)-(4-{[(<i>E</i>)-3,5-dibromo-2-
hydroxybenzylidene]amino}butyl)iminomethyl]phenol
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C18 H16 Br4 N2 O2'
_chemical_formula_sum     'C18 H16 Br4 N2 O2'
_chemical_formula_iupac     'C18 H16 Br4 N2 O2'
_chemical_formula_weight     611.97
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-P 2n 2ab'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,1/2-y,1/2+z
    3 1/2+x,1/2-y,-z
    4 -x,y,1/2-z
    5 -x,-y,-z
    6 1/2+x,1/2+y,1/2-z
    7 1/2-x,1/2+y,z
    8 x,-y,1/2+z
_cell_length_a     15.9537(12)
_cell_length_b     12.8784(10)
_cell_length_c     9.5566(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1963.5(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2045
_cell_measurement_theta_min     3.27
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     291(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     2.070
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1176
_exptl_absorpt_coefficient_mu     8.214
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(<i>SADABS</i>; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.1612
_exptl_absorpt_correction_T_max     0.4389
_exptl_special_details     ?
_diffrn_ambient_temperature     291(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 APEXII CCD area-detector
;
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15023
_diffrn_reflns_av_R_equivalents     0.0689
_diffrn_reflns_av_sigmaI/netI     0.0493
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     27.15
_diffrn_reflns_theta_full     27.15
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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     2164
_reflns_number_gt     1381
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0747
_refine_ls_R_factor_gt     0.0347
_refine_ls_wR_factor_gt     0.0650
_refine_ls_wR_factor_ref     0.0743
_refine_ls_goodness_of_fit_ref     0.993
_refine_ls_restrained_S_all     0.993
_refine_ls_number_reflns     2164
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0269P)^2^+1.1226P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.740
_refine_diff_density_min     -0.573
_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, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 0.13066(3) -0.24496(3) 0.17601(5) 0.0577(2) Uani d . 1.000 . .
    Br Br2 0.05752(3) 0.17551(3) 0.07666(5) 0.0549(2) Uani d . 1.000 . .
    O O1 0.25622(17) -0.15166(19) 0.3764(3) 0.0456(9) Uani d . 1.000 . .
    N N1 0.3337(2) -0.0051(2) 0.5060(3) 0.0374(11) Uani d . 1.000 . .
    C C1 0.2230(2) 0.0284(3) 0.3459(4) 0.0320(11) Uani d . 1.000 . .
    C C2 0.2109(2) -0.0776(3) 0.3154(4) 0.0324(11) Uani d . 1.000 . .
    C C3 0.1493(2) -0.1035(3) 0.2181(4) 0.0359(11) Uani d . 1.000 . .
    C C4 0.1036(2) -0.0293(3) 0.1493(4) 0.0373(12) Uani d . 1.000 . .
    C C5 0.1186(2) 0.0745(3) 0.1788(4) 0.0373(12) Uani d . 1.000 . .
    C C6 0.1761(2) 0.1035(3) 0.2756(4) 0.0349(11) Uani d . 1.000 . .
    C C7 0.2860(2) 0.0599(3) 0.4468(4) 0.0360(12) Uani d . 1.000 . .
    C C8 0.3979(2) 0.0338(3) 0.6028(4) 0.0433(14) Uani d . 1.000 . .
    C C9 0.4818(3) 0.0488(3) 0.5281(5) 0.0537(17) Uani d . 1.000 . .
    H H1 0.28180 -0.12680 0.42830 0.0680 Uiso d R 1.000 . .
    H H3 0.06320 -0.04820 0.08400 0.0450 Uiso c R 1.000 . .
    H H6 0.18440 0.17350 0.29520 0.0420 Uiso c R 1.000 . .
    H H7 0.29150 0.13000 0.46860 0.0430 Uiso c R 1.000 . .
    H H8A 0.40490 -0.01510 0.67920 0.0520 Uiso c R 1.000 . .
    H H8B 0.37970 0.09950 0.64210 0.0520 Uiso c R 1.000 . .
    H H9A 0.47400 0.09730 0.45150 0.0650 Uiso c R 1.000 . .
    H H9B 0.52140 0.07960 0.59310 0.0650 Uiso c R 1.000 . .
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 0.0699(3) 0.0317(2) 0.0716(3) -0.0021(2) -0.0215(3) -0.0097(2)
    Br2 0.0590(3) 0.0417(2) 0.0641(3) 0.0064(2) -0.0152(2) 0.0100(2)
    O1 0.0460(17) 0.0348(14) 0.0561(18) 0.0052(13) -0.0166(14) -0.0036(13)
    N1 0.0298(17) 0.0403(18) 0.042(2) -0.0008(16) -0.0012(16) -0.0022(15)
    C1 0.027(2) 0.0309(19) 0.038(2) -0.0025(17) 0.0029(19) 0.0002(17)
    C2 0.029(2) 0.0313(19) 0.037(2) 0.0010(17) 0.0004(18) 0.0008(17)
    C3 0.037(2) 0.0267(18) 0.044(2) -0.0035(18) 0.0021(19) -0.0057(17)
    C4 0.035(2) 0.038(2) 0.039(2) -0.0024(19) -0.0080(19) -0.0016(18)
    C5 0.033(2) 0.034(2) 0.045(2) 0.0023(18) -0.0035(19) 0.0043(18)
    C6 0.038(2) 0.0258(18) 0.041(2) -0.0018(17) 0.005(2) -0.0003(17)
    C7 0.037(2) 0.034(2) 0.037(2) -0.0042(18) 0.003(2) -0.0058(18)
    C8 0.038(2) 0.053(3) 0.039(2) -0.003(2) -0.006(2) -0.006(2)
    C9 0.043(3) 0.049(3) 0.069(3) -0.003(2) -0.013(3) -0.011(2)
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Br1 C3 . . 1.889(4) no
    Br2 C5 . . 1.896(4) no
    O1 C2 . . 1.331(5) no
    O1 H1 . . 0.7200 no
    N1 C7 . . 1.265(5) no
    N1 C8 . . 1.468(5) no
    C1 C2 . . 1.409(5) no
    C1 C6 . . 1.395(5) no
    C1 C7 . . 1.451(5) no
    C2 C3 . . 1.393(5) no
    C3 C4 . . 1.370(5) no
    C4 C5 . . 1.387(5) no
    C5 C6 . . 1.355(5) no
    C8 C9 . . 1.529(6) no
    C9 C9 . 5_656 1.485(6) no
    C4 H3 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C7 H7 . . 0.9300 no
    C8 H8A . . 0.9700 no
    C8 H8B . . 0.9700 no
    C9 H9A . . 0.9700 no
    C9 H9B . . 0.9700 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 O1 H1 . . . 107.00 no
    C7 N1 C8 . . . 118.4(3) no
    C2 C1 C6 . . . 119.9(3) no
    C2 C1 C7 . . . 120.2(3) no
    C6 C1 C7 . . . 119.9(3) no
    O1 C2 C3 . . . 120.3(3) no
    C1 C2 C3 . . . 117.8(3) no
    O1 C2 C1 . . . 121.9(3) no
    Br1 C3 C2 . . . 118.9(3) no
    C2 C3 C4 . . . 121.9(4) no
    Br1 C3 C4 . . . 119.1(3) no
    C3 C4 C5 . . . 118.9(3) no
    Br2 C5 C6 . . . 120.7(3) no
    C4 C5 C6 . . . 121.4(3) no
    Br2 C5 C4 . . . 117.9(3) no
    C1 C6 C5 . . . 120.0(4) no
    N1 C7 C1 . . . 121.9(3) no
    N1 C8 C9 . . . 111.1(3) no
    C8 C9 C9 . . 5_656 113.8(3) no
    C3 C4 H3 . . . 121.00 no
    C5 C4 H3 . . . 121.00 no
    C1 C6 H6 . . . 120.00 no
    C5 C6 H6 . . . 120.00 no
    N1 C7 H7 . . . 119.00 no
    C1 C7 H7 . . . 119.00 no
    N1 C8 H8A . . . 109.00 no
    N1 C8 H8B . . . 109.00 no
    C9 C8 H8A . . . 109.00 no
    C9 C8 H8B . . . 109.00 no
    H8A C8 H8B . . . 108.00 no
    C8 C9 H9A . . . 109.00 no
    C8 C9 H9B . . . 109.00 no
    H9A C9 H9B . . . 108.00 no
    C9 C9 H9A 5_656 . . 109.00 no
    C9 C9 H9B 5_656 . . 109.00 no
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
    C8 N1 C7 C1 . . . . 177.7(3) no
    C7 N1 C8 C9 . . . . -94.4(4) no
    C6 C1 C2 O1 . . . . 177.7(3) no
    C6 C1 C2 C3 . . . . -2.3(5) no
    C7 C1 C2 O1 . . . . -0.3(5) no
    C7 C1 C2 C3 . . . . 179.7(3) no
    C2 C1 C6 C5 . . . . 0.4(5) no
    C7 C1 C6 C5 . . . . 178.4(3) no
    C2 C1 C7 N1 . . . . 2.7(5) no
    C6 C1 C7 N1 . . . . -175.2(3) no
    O1 C2 C3 Br1 . . . . 0.6(5) no
    O1 C2 C3 C4 . . . . -177.5(3) no
    C1 C2 C3 Br1 . . . . -179.4(3) no
    C1 C2 C3 C4 . . . . 2.5(5) no
    Br1 C3 C4 C5 . . . . -178.9(3) no
    C2 C3 C4 C5 . . . . -0.8(5) no
    C3 C4 C5 Br2 . . . . 177.6(3) no
    C3 C4 C5 C6 . . . . -1.2(5) no
    Br2 C5 C6 C1 . . . . -177.4(3) no
    C4 C5 C6 C1 . . . . 1.4(5) no
    N1 C8 C9 C9 . . . 5_656 -62.9(5) no
    C8 C9 C9 C8 . . 5_656 5_656 -180.0(3) no
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 . 0.72 1.92 2.574(4) 151 y
    C6 H6 O1 7_555 0.93 2.56 3.469(5) 165 y
    C4 H3 Br2 5 0.93 2.96 3.849(4) 161 y