#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/61/2236174.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236174
loop_
_publ_author_name
'Zhang, Dingjun'
'Yu, Hong'
'Jin, Yue-Bao'
'Lei, Ke-Wei'
_publ_section_title
;
 Bis{2,4-dibromo-6-[(E)-(4-fluorobenzyl)iminomethyl]phenolato-κ²N,O}zinc
;
_journal_coeditor_code           DS2215
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1424
_journal_paper_doi               10.1107/S1600536812043930
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Zn (C14 H9 Br2 F N O)2]'
_chemical_formula_moiety         'C28 H18 Br4 F2 N2 O2 Zn'
_chemical_formula_sum            'C28 H18 Br4 F2 N2 O2 Zn'
_chemical_formula_weight         837.43
_chemical_name_systematic
;
Bis{2,4-dibromo-6-[(E)-(4-fluorobenzyl)iminomethyl]phenolato-
κ²N,O}zinc
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 133.490(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.6277(11)
_cell_length_b                   9.8273(3)
_cell_length_c                   13.0879(10)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.82
_cell_volume                     1364.9(3)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16865
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    6.799
_exptl_absorpt_correction_T_max  0.442
_exptl_absorpt_correction_T_min  0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.038
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.240
_refine_ls_abs_structure_details 'Flack (1983), 1307 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.009(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0167
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0207P)²+0.6898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0404
_refine_ls_wR_factor_ref         0.0406
_reflns_number_gt                2733
_reflns_number_total             2785
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ds2215.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'C 2Y'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2236174
_cod_database_fobs_code          2236174
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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_symmetry_multiplicity
Br Br1 1.04547(2) 0.46777(3) 1.37836(3) 0.04434(8) Uani d . 1 1
Br Br2 0.66508(3) 0.09397(3) 1.20503(3) 0.05004(8) Uani d . 1 1
Zn Zn1 1.0000 0.30224(4) 1.0000 0.03419(10) Uani d S 1 2
F F1 1.0457(3) -0.1547(3) 0.6672(3) 0.1080(9) Uani d . 1 1
O O1 0.97414(16) 0.36983(17) 1.11706(18) 0.0347(4) Uani d . 1 1
N N1 0.83087(19) 0.2066(2) 0.8654(2) 0.0366(5) Uani d . 1 1
C C1 0.9037(2) 0.3095(2) 1.1302(2) 0.0281(4) Uani d . 1 1
C C2 0.9183(2) 0.3416(2) 1.2459(3) 0.0310(5) Uani d . 1 1
C C3 0.8483(2) 0.2810(3) 1.2690(3) 0.0346(5) Uani d . 1 1
H H3 0.8609 0.3047 1.3467 0.042 Uiso calc R 1 1
C C4 0.7589(2) 0.1838(3) 1.1733(3) 0.0360(5) Uani d . 1 1
C C5 0.7374(2) 0.1507(3) 1.0573(3) 0.0356(5) Uani d . 1 1
H H5 0.6754 0.0874 0.9933 0.043 Uiso calc R 1 1
C C6 0.8086(2) 0.2117(2) 1.0336(3) 0.0314(5) Uani d . 1 1
C C7 0.7726(2) 0.1769(3) 0.9027(3) 0.0364(5) Uani d . 1 1
H H7 0.6986 0.1271 0.8384 0.044 Uiso calc R 1 1
C C8 0.7676(2) 0.1760(3) 0.7192(3) 0.0445(6) Uani d . 1 1
H H8A 0.7485 0.2608 0.6700 0.053 Uiso calc R 1 1
H H8B 0.6883 0.1305 0.6725 0.053 Uiso calc R 1 1
C C9 0.8450(2) 0.0878(3) 0.7088(3) 0.0373(5) Uani d . 1 1
C C10 0.9129(3) -0.0210(4) 0.7977(3) 0.0583(8) Uani d . 1 1
H H10 0.9133 -0.0392 0.8677 0.070 Uiso calc R 1 1
C C11 0.9809(4) -0.1039(4) 0.7839(5) 0.0726(11) Uani d . 1 1
H H11 1.0268 -0.1776 0.8438 0.087 Uiso calc R 1 1
C C12 0.9785(3) -0.0746(4) 0.6806(4) 0.0613(9) Uani d . 1 1
C C13 0.9123(3) 0.0310(4) 0.5906(3) 0.0547(8) Uani d . 1 1
H H13 0.9120 0.0479 0.5205 0.066 Uiso calc R 1 1
C C14 0.8450(2) 0.1132(3) 0.6051(3) 0.0419(6) Uani d . 1 1
H H14 0.7993 0.1863 0.5443 0.050 Uiso calc R 1 1
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Zn Zn 0.2839 1.4301 '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'
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
O1 Zn1 O1 . 2_757 139.77(10)
O1 Zn1 N1 . . 93.47(7)
O1 Zn1 N1 2_757 . 104.97(8)
O1 Zn1 N1 . 2_757 104.97(8)
O1 Zn1 N1 2_757 2_757 93.47(7)
N1 Zn1 N1 . 2_757 124.76(13)
C1 O1 Zn1 . . 123.68(15)
C7 N1 C8 . . 117.5(2)
C7 N1 Zn1 . . 120.79(17)
C8 N1 Zn1 . . 121.59(16)
O1 C1 C2 . . 119.5(2)
O1 C1 C6 . . 124.7(2)
C2 C1 C6 . . 115.9(2)
C3 C2 C1 . . 123.3(2)
C3 C2 Br1 . . 119.44(18)
C1 C2 Br1 . . 117.22(16)
C2 C3 C4 . . 118.5(2)
C2 C3 H3 . . 120.7
C4 C3 H3 . . 120.7
C5 C4 C3 . . 121.3(2)
C5 C4 Br2 . . 119.04(19)
C3 C4 Br2 . . 119.68(18)
C4 C5 C6 . . 120.4(2)
C4 C5 H5 . . 119.8
C6 C5 H5 . . 119.8
C5 C6 C1 . . 120.6(2)
C5 C6 C7 . . 116.0(2)
C1 C6 C7 . . 123.2(2)
N1 C7 C6 . . 127.3(2)
N1 C7 H7 . . 116.3
C6 C7 H7 . . 116.3
N1 C8 C9 . . 113.3(2)
N1 C8 H8A . . 108.9
C9 C8 H8A . . 108.9
N1 C8 H8B . . 108.9
C9 C8 H8B . . 108.9
H8A C8 H8B . . 107.7
C10 C9 C14 . . 118.9(3)
C10 C9 C8 . . 121.4(2)
C14 C9 C8 . . 119.7(2)
C9 C10 C11 . . 120.7(3)
C9 C10 H10 . . 119.6
C11 C10 H10 . . 119.6
C12 C11 C10 . . 118.3(3)
C12 C11 H11 . . 120.9
C10 C11 H11 . . 120.9
C13 C12 C11 . . 122.7(3)
C13 C12 F1 . . 118.6(3)
C11 C12 F1 . . 118.7(3)
C12 C13 C14 . . 118.6(3)
C12 C13 H13 . . 120.7
C14 C13 H13 . . 120.7
C9 C14 C13 . . 120.8(3)
C9 C14 H14 . . 119.6
C13 C14 H14 . . 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C2 . 1.888(2)
Br2 C4 . 1.902(2)
Zn1 O1 . 1.9311(16)
Zn1 O1 2_757 1.9311(17)
Zn1 N1 . 2.027(2)
Zn1 N1 2_757 2.027(2)
F1 C12 . 1.361(4)
O1 C1 . 1.299(3)
N1 C7 . 1.274(3)
N1 C8 . 1.473(3)
C1 C2 . 1.412(3)
C1 C6 . 1.427(3)
C2 C3 . 1.384(3)
C3 C4 . 1.392(4)
C3 H3 . 0.9300
C4 C5 . 1.362(3)
C5 C6 . 1.408(3)
C5 H5 . 0.9300
C6 C7 . 1.446(3)
C7 H7 . 0.9300
C8 C9 . 1.505(4)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.375(4)
C9 C14 . 1.380(4)
C10 C11 . 1.390(5)
C10 H10 . 0.9300
C11 C12 . 1.360(5)
C11 H11 . 0.9300
C12 C13 . 1.353(5)
C13 C14 . 1.384(4)
C13 H13 . 0.9300
C14 H14 . 0.9300
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
O1 Zn1 O1 C1 2_757 145.92(19)
N1 Zn1 O1 C1 . 27.73(19)
N1 Zn1 O1 C1 2_757 -99.68(19)
O1 Zn1 N1 C7 . -20.3(2)
O1 Zn1 N1 C7 2_757 -164.2(2)
N1 Zn1 N1 C7 2_757 90.6(2)
O1 Zn1 N1 C8 . 156.2(2)
O1 Zn1 N1 C8 2_757 12.3(2)
N1 Zn1 N1 C8 2_757 -92.9(2)
Zn1 O1 C1 C2 . 161.59(16)
Zn1 O1 C1 C6 . -19.3(3)
O1 C1 C2 C3 . -179.2(2)
C6 C1 C2 C3 . 1.7(3)
O1 C1 C2 Br1 . -2.1(3)
C6 C1 C2 Br1 . 178.73(17)
C1 C2 C3 C4 . -0.2(4)
Br1 C2 C3 C4 . -177.20(19)
C2 C3 C4 C5 . -1.7(4)
C2 C3 C4 Br2 . 177.87(19)
C3 C4 C5 C6 . 1.9(4)
Br2 C4 C5 C6 . -177.63(19)
C4 C5 C6 C1 . -0.3(4)
C4 C5 C6 C7 . -175.8(2)
O1 C1 C6 C5 . 179.5(2)
C2 C1 C6 C5 . -1.4(3)
O1 C1 C6 C7 . -5.3(4)
C2 C1 C6 C7 . 173.8(2)
C8 N1 C7 C6 . -172.0(3)
Zn1 N1 C7 C6 . 4.6(4)
C5 C6 C7 N1 . -171.5(3)
C1 C6 C7 N1 . 13.1(4)
C7 N1 C8 C9 . -124.7(3)
Zn1 N1 C8 C9 . 58.7(3)
N1 C8 C9 C10 . 41.3(4)
N1 C8 C9 C14 . -140.9(3)
C14 C9 C10 C11 . 0.2(5)
C8 C9 C10 C11 . 178.0(3)
C9 C10 C11 C12 . 0.1(6)
C10 C11 C12 C13 . -0.4(6)
C10 C11 C12 F1 . 179.5(3)
C11 C12 C13 C14 . 0.5(5)
F1 C12 C13 C14 . -179.4(3)
C10 C9 C14 C13 . -0.1(4)
C8 C9 C14 C13 . -178.0(3)
C12 C13 C14 C9 . -0.2(4)
