##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-11-04
_journal_date_accepted     2009-11-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     12
_journal_page_first     o3154
_journal_page_last     o3154
_journal_paper_category     QO
_journal_coeditor_code     LX2124
_publ_contact_author_name     'Li Xu'
_publ_contact_author_address
;
 School of Chemical and Biological Engineering
 Lanzhou Jiaotong University
 Lanzhou 730070
 People's Republic of China
;
_publ_contact_author_email     xuli@mail.lzjtu.cn
_publ_contact_author_fax     '0086 931 4956512'
_publ_contact_author_phone     '0086 931 4939265'
_publ_section_title
;
4-Bromo-2-{(E)-3-[1-(hydroxyimino)ethyl]phenyliminomethyl}phenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Xu, Li'
;
 School of Chemical and Biological Engineering
 Lanzhou Jiaotong University
 Lanzhou 730070
 People's Republic of China
;
    'Wu, Lei'
;
 School of Chemical and Biological Engineering
 Lanzhou Jiaotong University
 Lanzhou 730070
 People's Republic of China
;
data_I
_chemical_name_systematic
;
4-Bromo-2-{(E)-3-[1-(hydroxyimino)ethyl]phenyliminomethyl}phenol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H13 Br N2 O2'
_chemical_formula_sum     'C15 H13 Br N2 O2'
_chemical_formula_iupac     'C15 H13 Br N2 O2'
_chemical_formula_weight     333.18
_chemical_melting_point     ?
_chemical_melting_point_gt     459
_chemical_melting_point_lt     461
_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     17.020(2)
_cell_length_b     6.1676(7)
_cell_length_c     13.6930(10)
_cell_angle_alpha     90.00
_cell_angle_beta     96.4610(10)
_cell_angle_gamma     90.00
_cell_volume     1428.3(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2173
_cell_measurement_theta_min     2.718
_cell_measurement_theta_max     23.774
_cell_measurement_temperature     298(2)
_exptl_crystal_description     needle-like
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.549
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     672
_exptl_absorpt_coefficient_mu     2.880
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.3573
_exptl_absorpt_correction_T_max     0.7616
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_measurement_device_type     'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     6906
_diffrn_reflns_av_R_equivalents     0.0511
_diffrn_reflns_av_sigmaI/netI     0.0596
_diffrn_reflns_theta_min     2.41
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_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     14
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_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     2492
_reflns_number_gt     1799
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0619
_refine_ls_R_factor_gt     0.0386
_refine_ls_wR_factor_gt     0.0904
_refine_ls_wR_factor_ref     0.1003
_refine_ls_goodness_of_fit_ref     0.991
_refine_ls_restrained_S_all     0.991
_refine_ls_number_reflns     2492
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0498P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.467
_refine_diff_density_min     -0.323
_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'
    'O' 'O' 0.0106 0.0060
                         '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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT (Siemens, 1996)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                     'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material     'SHELXTL (Sheldrick, 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 Br 0.46909(2) -0.34895(6) 0.66885(3) 0.05662(19) Uani d . 1 . .
    N N1 0.04843(18) 1.3049(4) 0.46740(19) 0.0451(7) Uani d . 1 . .
    N N2 0.25065(15) 0.4933(4) 0.52712(19) 0.0416(7) Uani d . 1 . .
    O O1 0.01134(16) 1.4311(4) 0.38885(16) 0.0609(8) Uani d . 1 . .
    H H1 -0.0096 1.5373 0.4110 0.091 Uiso calc R 1 . .
    O O2 0.29339(17) 0.2760(5) 0.37605(18) 0.0688(8) Uani d . 1 . .
    H H2 0.2718 0.3726 0.4044 0.103 Uiso calc R 1 . .
    C C1 0.0818(3) 1.0731(7) 0.3317(2) 0.0601(11) Uani d . 1 . .
    H H1A 0.0385 1.1454 0.2940 0.090 Uiso calc R 1 . .
    H H1B 0.0753 0.9191 0.3247 0.090 Uiso calc R 1 . .
    H H1C 0.1306 1.1160 0.3084 0.090 Uiso calc R 1 . .
    C C2 0.0833(2) 1.1340(5) 0.4385(2) 0.0355(8) Uani d . 1 . .
    C C3 0.12600(18) 0.9934(5) 0.5170(2) 0.0328(7) Uani d . 1 . .
    C C4 0.16790(19) 0.8077(5) 0.4921(2) 0.0361(8) Uani d . 1 . .
    H H4 0.1683 0.7723 0.4261 0.043 Uiso calc R 1 . .
    C C5 0.2089(2) 0.6749(5) 0.5637(2) 0.0372(8) Uani d . 1 . .
    C C6 0.2088(2) 0.7269(6) 0.6638(2) 0.0457(9) Uani d . 1 . .
    H H6 0.2355 0.6402 0.7123 0.055 Uiso calc R 1 . .
    C C7 0.1674(2) 0.9129(6) 0.6892(2) 0.0541(10) Uani d . 1 . .
    H H7 0.1670 0.9486 0.7551 0.065 Uiso calc R 1 . .
    C C8 0.1272(2) 1.0439(6) 0.6175(2) 0.0439(9) Uani d . 1 . .
    H H8 0.1007 1.1664 0.6362 0.053 Uiso calc R 1 . .
    C C9 0.2887(2) 0.3533(5) 0.5848(2) 0.0402(8) Uani d . 1 . .
    H H9 0.2886 0.3675 0.6524 0.048 Uiso calc R 1 . .
    C C10 0.33200(19) 0.1729(5) 0.5462(2) 0.0370(8) Uani d . 1 . .
    C C11 0.3322(2) 0.1382(6) 0.4443(3) 0.0455(9) Uani d . 1 . .
    C C12 0.3730(2) -0.0397(6) 0.4104(3) 0.0554(10) Uani d . 1 . .
    H H12 0.3726 -0.0625 0.3432 0.067 Uiso calc R 1 . .
    C C13 0.4141(2) -0.1828(6) 0.4770(3) 0.0520(10) Uani d . 1 . .
    H H13 0.4413 -0.3000 0.4544 0.062 Uiso calc R 1 . .
    C C14 0.4138(2) -0.1477(5) 0.5778(2) 0.0391(8) Uani d . 1 . .
    C C15 0.37336(19) 0.0263(5) 0.6123(2) 0.0393(8) Uani d . 1 . .
    H H15 0.3735 0.0467 0.6797 0.047 Uiso calc R 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
    Br 0.0571(3) 0.0476(3) 0.0643(3) 0.01472(19) 0.0030(2) 0.00954(19)
    N1 0.056(2) 0.0395(17) 0.0372(15) 0.0112(15) -0.0063(14) 0.0022(13)
    N2 0.0357(17) 0.0356(17) 0.0537(17) 0.0027(13) 0.0058(14) 0.0020(13)
    O1 0.083(2) 0.0526(16) 0.0436(13) 0.0295(15) -0.0089(13) 0.0039(12)
    O2 0.078(2) 0.079(2) 0.0479(14) 0.0289(17) 0.0001(15) 0.0108(14)
    C1 0.081(3) 0.062(2) 0.0367(19) 0.028(2) 0.0017(19) -0.0001(18)
    C2 0.036(2) 0.0329(19) 0.0373(17) -0.0002(15) 0.0027(15) -0.0020(14)
    C3 0.0309(19) 0.0315(18) 0.0353(16) 0.0001(14) 0.0005(14) 0.0005(14)
    C4 0.037(2) 0.037(2) 0.0338(16) -0.0039(15) 0.0021(15) -0.0024(14)
    C5 0.0311(19) 0.0339(19) 0.0462(19) -0.0012(14) 0.0031(15) 0.0022(15)
    C6 0.051(2) 0.043(2) 0.043(2) 0.0113(18) 0.0038(17) 0.0141(16)
    C7 0.071(3) 0.058(2) 0.0331(18) 0.014(2) 0.0074(18) 0.0027(17)
    C8 0.052(2) 0.040(2) 0.0395(18) 0.0097(17) 0.0060(17) 0.0024(16)
    C9 0.040(2) 0.0346(19) 0.0455(19) -0.0010(16) 0.0020(16) -0.0017(16)
    C10 0.0321(19) 0.0332(19) 0.0443(18) -0.0013(15) -0.0016(15) 0.0004(15)
    C11 0.037(2) 0.050(2) 0.048(2) 0.0033(17) 0.0018(17) 0.0052(18)
    C12 0.057(3) 0.070(3) 0.0408(19) 0.012(2) 0.0101(18) -0.0030(19)
    C13 0.051(3) 0.051(2) 0.055(2) 0.0117(18) 0.0109(19) -0.0053(18)
    C14 0.034(2) 0.0331(19) 0.050(2) -0.0024(16) 0.0022(16) 0.0017(15)
    C15 0.038(2) 0.038(2) 0.0411(18) 0.0003(16) 0.0013(16) -0.0041(15)
_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
    Br C14 . 1.928(3) ?
    Br Br 2_656 3.8768(5) ?
    Br Br 2_646 3.8768(5) ?
    N1 C2 . 1.293(4) ?
    N1 O1 . 1.417(3) ?
    N2 C9 . 1.294(4) ?
    N2 C5 . 1.446(4) ?
    O1 H1 . 0.8200 ?
    O2 C11 . 1.377(4) ?
    O2 H2 . 0.8200 ?
    C1 C2 . 1.507(4) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C3 . 1.504(4) ?
    C3 C8 . 1.409(4) ?
    C3 C4 . 1.411(4) ?
    C4 C5 . 1.401(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.409(5) ?
    C6 C7 . 1.410(5) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.390(5) ?
    C7 H7 . 0.9300 ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.466(4) ?
    C9 H9 . 0.9300 ?
    C10 C15 . 1.411(4) ?
    C10 C11 . 1.411(5) ?
    C11 C12 . 1.405(5) ?
    C12 C13 . 1.399(5) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.398(5) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.387(4) ?
    C15 H15 . 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
    C14 Br Br . 2_656 86.56(10) ?
    C14 Br Br . 2_646 164.58(10) ?
    Br Br Br 2_656 2_646 105.395(19) ?
    C2 N1 O1 . . 113.3(3) ?
    C9 N2 C5 . . 122.5(3) ?
    N1 O1 H1 . . 109.5 ?
    C11 O2 H2 . . 109.5 ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 C3 . . 116.9(3) ?
    N1 C2 C1 . . 122.8(3) ?
    C3 C2 C1 . . 120.2(3) ?
    C8 C3 C4 . . 117.6(3) ?
    C8 C3 C2 . . 121.6(3) ?
    C4 C3 C2 . . 120.8(3) ?
    C5 C4 C3 . . 122.0(3) ?
    C5 C4 H4 . . 119.0 ?
    C3 C4 H4 . . 119.0 ?
    C4 C5 C6 . . 119.5(3) ?
    C4 C5 N2 . . 115.8(3) ?
    C6 C5 N2 . . 124.6(3) ?
    C5 C6 C7 . . 118.7(3) ?
    C5 C6 H6 . . 120.6 ?
    C7 C6 H6 . . 120.6 ?
    C8 C7 C6 . . 121.3(3) ?
    C8 C7 H7 . . 119.4 ?
    C6 C7 H7 . . 119.4 ?
    C7 C8 C3 . . 120.9(3) ?
    C7 C8 H8 . . 119.6 ?
    C3 C8 H8 . . 119.6 ?
    N2 C9 C10 . . 121.6(3) ?
    N2 C9 H9 . . 119.2 ?
    C10 C9 H9 . . 119.2 ?
    C15 C10 C11 . . 118.7(3) ?
    C15 C10 C9 . . 119.3(3) ?
    C11 C10 C9 . . 122.0(3) ?
    O2 C11 C12 . . 118.3(3) ?
    O2 C11 C10 . . 121.5(3) ?
    C12 C11 C10 . . 120.1(3) ?
    C13 C12 C11 . . 120.4(3) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C14 C13 C12 . . 119.3(3) ?
    C14 C13 H13 . . 120.4 ?
    C12 C13 H13 . . 120.4 ?
    C15 C14 C13 . . 120.9(3) ?
    C15 C14 Br . . 120.2(2) ?
    C13 C14 Br . . 118.9(2) ?
    C14 C15 C10 . . 120.5(3) ?
    C14 C15 H15 . . 119.7 ?
    C10 C15 H15 . . 119.7 ?
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
    O1 N1 C2 C3 . . . . 178.5(3) ?
    O1 N1 C2 C1 . . . . -1.9(5) ?
    N1 C2 C3 C8 . . . . 0.8(5) ?
    C1 C2 C3 C8 . . . . -178.8(3) ?
    N1 C2 C3 C4 . . . . -177.9(3) ?
    C1 C2 C3 C4 . . . . 2.5(5) ?
    C8 C3 C4 C5 . . . . 0.6(5) ?
    C2 C3 C4 C5 . . . . 179.4(3) ?
    C3 C4 C5 C6 . . . . -0.1(5) ?
    C3 C4 C5 N2 . . . . -178.6(3) ?
    C9 N2 C5 C4 . . . . -177.6(3) ?
    C9 N2 C5 C6 . . . . 4.0(5) ?
    C4 C5 C6 C7 . . . . -0.3(5) ?
    N2 C5 C6 C7 . . . . 178.1(3) ?
    C5 C6 C7 C8 . . . . 0.0(6) ?
    C6 C7 C8 C3 . . . . 0.6(6) ?
    C4 C3 C8 C7 . . . . -0.9(5) ?
    C2 C3 C8 C7 . . . . -179.6(3) ?
    C5 N2 C9 C10 . . . . -178.8(3) ?
    N2 C9 C10 C15 . . . . 179.2(3) ?
    N2 C9 C10 C11 . . . . -2.2(5) ?
    C15 C10 C11 O2 . . . . -179.6(3) ?
    C9 C10 C11 O2 . . . . 1.8(5) ?
    C15 C10 C11 C12 . . . . 0.1(5) ?
    C9 C10 C11 C12 . . . . -178.5(3) ?
    O2 C11 C12 C13 . . . . 179.2(4) ?
    C10 C11 C12 C13 . . . . -0.5(6) ?
    C11 C12 C13 C14 . . . . 0.4(6) ?
    C12 C13 C14 C15 . . . . 0.0(5) ?
    C12 C13 C14 Br . . . . 178.9(3) ?
    Br Br C14 C15 2_656 . . . -39.2(3) ?
    Br Br C14 C15 2_646 . . . 102.3(4) ?
    Br Br C14 C13 2_656 . . . 141.9(3) ?
    Br Br C14 C13 2_646 . . . -76.7(5) ?
    C13 C14 C15 C10 . . . . -0.4(5) ?
    Br C14 C15 C10 . . . . -179.3(2) ?
    C11 C10 C15 C14 . . . . 0.3(5) ?
    C9 C10 C15 C14 . . . . 179.0(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
    O1 H1 N1 3_586 0.82 2.10 2.830(4) 148.5 y
    O2 H2 N2 . 0.82 1.91 2.635(4) 147.0 y
