#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/52/2235249.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_2235249
loop_
_publ_author_name
'Kargar, Hadi'
'Kia, Reza'
'Tahir, Muhammad Nawaz'
_publ_section_title
;
 {4,4',6,6'-Tetrabromo-2,2'-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]diphenolato}nickel(II)
;
_journal_coeditor_code           SU2421
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m753
_journal_paper_doi               10.1107/S1600536812020375
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Ni (C19 H16 Br4 N2 O2)]'
_chemical_formula_moiety         'C19 H16 Br4 N2 Ni O2'
_chemical_formula_sum            'C19 H16 Br4 N2 Ni O2'
_chemical_formula_weight         682.69
_chemical_name_systematic
{4,4',6,6'-Tetrabromo-2,2'-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]diphenolato}nickel(II)
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1125(11)
_cell_length_b                   15.4789(12)
_cell_length_c                   8.4734(5)
_cell_measurement_reflns_used    2540
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.45
_cell_volume                     2113.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and 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  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16236
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.499
_exptl_absorpt_correction_T_max  0.8710
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            dark-red
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.783
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0387P)²+0.4809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                1574
_reflns_number_total             2086
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2421.cif
_cod_data_source_block           I
_cod_database_code               2235249
_cod_database_fobs_code          2235249
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'
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 0.34274(3) -0.24016(2) 0.18392(5) 0.04218(15) Uani d . 1 1
Br Br2 0.10156(3) -0.05088(3) -0.14763(7) 0.06551(19) Uani d . 1 1
Ni Ni1 0.5000 0.02131(4) 0.2500 0.02663(17) Uani d S 1 2
O O1 0.43065(15) -0.06700(15) 0.1850(3) 0.0344(6) Uani d . 1 1
N N1 0.44411(18) 0.10588(18) 0.1331(3) 0.0281(7) Uani d . 1 1
C C1 0.3595(2) -0.0600(2) 0.1155(4) 0.0284(8) Uani d . 1 1
C C2 0.3081(2) -0.1331(2) 0.0964(4) 0.0293(8) Uani d . 1 1
C C3 0.2334(2) -0.1309(3) 0.0186(4) 0.0337(9) Uani d . 1 1
H H3 0.2019 -0.1809 0.0073 0.040 Uiso calc R 1 1
C C4 0.2054(2) -0.0533(3) -0.0427(4) 0.0372(9) Uani d . 1 1
C C5 0.2510(2) 0.0203(3) -0.0270(5) 0.0391(10) Uani d . 1 1
H H5 0.2312 0.0721 -0.0681 0.047 Uiso calc R 1 1
C C6 0.3279(2) 0.0180(2) 0.0515(4) 0.0304(8) Uani d . 1 1
C C7 0.3763(2) 0.0952(2) 0.0563(4) 0.0317(8) Uani d . 1 1
H H7 0.3569 0.1420 -0.0017 0.038 Uiso calc R 1 1
C C8 0.4910(2) 0.1859(2) 0.1043(4) 0.0334(9) Uani d . 1 1
H H8A 0.4631 0.2189 0.0227 0.040 Uiso calc R 1 1
H H8B 0.5458 0.1711 0.0655 0.040 Uiso calc R 1 1
C C9 0.5000 0.2419(3) 0.2500 0.0320(12) Uani d S 1 2
C C10 0.4239(3) 0.2995(3) 0.2735(5) 0.0499(11) Uani d . 1 1
H H10A 0.3746 0.2647 0.2718 0.075 Uiso calc R 1 1
H H10B 0.4213 0.3415 0.1901 0.075 Uiso calc R 1 1
H H10C 0.4280 0.3286 0.3732 0.075 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'
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'
Ni Ni 0.3393 1.1124 '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'
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 Ni1 O1 . 3_655 84.69(15)
O1 Ni1 N1 . 3_655 164.78(11)
O1 Ni1 N1 3_655 3_655 93.94(11)
O1 Ni1 N1 . . 93.94(11)
O1 Ni1 N1 3_655 . 164.78(11)
N1 Ni1 N1 3_655 . 91.27(17)
C1 O1 Ni1 . . 127.5(2)
C7 N1 C8 . . 117.5(3)
C7 N1 Ni1 . . 126.0(3)
C8 N1 Ni1 . . 115.5(2)
O1 C1 C2 . . 120.4(3)
O1 C1 C6 . . 124.4(3)
C2 C1 C6 . . 115.3(3)
C3 C2 C1 . . 123.3(3)
C3 C2 Br1 . . 117.8(3)
C1 C2 Br1 . . 118.8(3)
C2 C3 C4 . . 119.2(3)
C2 C3 H3 . . 120.4
C4 C3 H3 . . 120.4
C5 C4 C3 . . 120.9(3)
C5 C4 Br2 . . 120.4(3)
C3 C4 Br2 . . 118.7(3)
C4 C5 C6 . . 120.0(4)
C4 C5 H5 . . 120.0
C6 C5 H5 . . 120.0
C5 C6 C1 . . 121.3(3)
C5 C6 C7 . . 118.3(3)
C1 C6 C7 . . 120.3(3)
N1 C7 C6 . . 126.0(3)
N1 C7 H7 . . 117.0
C6 C7 H7 . . 117.0
N1 C8 C9 . . 113.3(3)
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
C8 C9 C8 . 3_655 110.2(4)
C8 C9 C10 . 3_655 107.7(2)
C8 C9 C10 3_655 3_655 111.3(2)
C8 C9 C10 . . 111.3(2)
C8 C9 C10 3_655 . 107.7(2)
C10 C9 C10 3_655 . 108.7(5)
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C2 . 1.899(3)
Br2 C4 . 1.895(4)
Ni1 O1 . 1.849(2)
Ni1 O1 3_655 1.849(2)
Ni1 N1 3_655 1.872(3)
Ni1 N1 . 1.872(3)
O1 C1 . 1.293(4)
N1 C7 . 1.282(4)
N1 C8 . 1.471(4)
C1 C2 . 1.412(5)
C1 C6 . 1.418(5)
C2 C3 . 1.373(5)
C3 C4 . 1.384(5)
C3 H3 . 0.9300
C4 C5 . 1.362(5)
C5 C6 . 1.407(5)
C5 H5 . 0.9300
C6 C7 . 1.428(5)
C7 H7 . 0.9300
C8 C9 . 1.515(4)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C8 3_655 1.515(4)
C9 C10 3_655 1.529(5)
C9 C10 . 1.529(5)
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
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_4
_geom_torsion
O1 Ni1 O1 C1 3_655 . -178.8(3)
N1 Ni1 O1 C1 3_655 . 95.7(5)
N1 Ni1 O1 C1 . . -14.0(3)
O1 Ni1 N1 C7 . . 6.6(3)
O1 Ni1 N1 C7 3_655 . 90.8(5)
N1 Ni1 N1 C7 3_655 . -159.1(4)
O1 Ni1 N1 C8 . . -161.3(2)
O1 Ni1 N1 C8 3_655 . -77.1(5)
N1 Ni1 N1 C8 3_655 . 32.97(18)
Ni1 O1 C1 C2 . . -169.7(2)
Ni1 O1 C1 C6 . . 11.5(5)
O1 C1 C2 C3 . . -177.4(3)
C6 C1 C2 C3 . . 1.5(5)
O1 C1 C2 Br1 . . 3.1(4)
C6 C1 C2 Br1 . . -177.9(2)
C1 C2 C3 C4 . . -1.1(5)
Br1 C2 C3 C4 . . 178.3(3)
C2 C3 C4 C5 . . 0.1(6)
C2 C3 C4 Br2 . . -179.3(3)
C3 C4 C5 C6 . . 0.5(6)
Br2 C4 C5 C6 . . 179.8(3)
C4 C5 C6 C1 . . -0.1(5)
C4 C5 C6 C7 . . 175.9(3)
O1 C1 C6 C5 . . 178.0(3)
C2 C1 C6 C5 . . -0.9(5)
O1 C1 C6 C7 . . 2.2(5)
C2 C1 C6 C7 . . -176.7(3)
C8 N1 C7 C6 . . 171.2(3)
Ni1 N1 C7 C6 . . 3.5(5)
C5 C6 C7 N1 . . 174.0(3)
C1 C6 C7 N1 . . -10.0(6)
C7 N1 C8 C9 . . 118.4(3)
Ni1 N1 C8 C9 . . -72.7(3)
N1 C8 C9 C8 . 3_655 35.2(2)
N1 C8 C9 C10 . 3_655 156.7(3)
N1 C8 C9 C10 . . -84.3(4)
