#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/98/2229885.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_2229885
loop_
_publ_author_name
'Harding, Phimphaka'
'Harding, David J.'
'Soponrat, Nitisastr'
'Adams, Harry'
_publ_section_title
;
 [4-Bromo-N-(pyridin-2-ylmethylidene)aniline-κ²N,N']bis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato-κ²O,O')nickel(II)
;
_journal_coeditor_code           ZB2010
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m404
_journal_page_last               m405
_journal_paper_doi               10.1107/S1600536811005599
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Ni (C5 H F6 O2)2 (C12 H9 Br N2)]'
_chemical_formula_moiety         'C22 H11 Br F12 N2 Ni O4'
_chemical_formula_sum            'C22 H11 Br F12 N2 Ni O4'
_chemical_formula_weight         733.95
_chemical_melting_point          429
_chemical_name_systematic
;
[4-Bromo-N-(pyridin-2-ylmethylidene)aniline-
κ²N,N']bis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato-
κ²O,O')nickel(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 103.952(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.251(8)
_cell_length_b                   10.006(3)
_cell_length_c                   17.653(5)
_cell_measurement_reflns_used    3767
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.37
_cell_volume                     5357(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.1450
_diffrn_reflns_av_sigmaI/netI    0.1198
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27645
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.34
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.332
_exptl_absorpt_correction_T_max  0.7835
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.236
_refine_diff_density_min         -1.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                3422
_reflns_number_total             5988
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zb2010.cif
_cod_data_source_block           I
_cod_original_cell_volume        5358(2)
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2229885
_cod_database_fobs_code          2229885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.089498(18) 0.60018(5) 0.17271(3) 0.01947(16) Uani d . 1 . .
Br Br1 0.279804(16) 0.50379(5) -0.01356(3) 0.03493(16) Uani d . 1 . .
N N1 0.10544(11) 0.4874(3) 0.0821(2) 0.0180(8) Uani d . 1 . .
N N2 0.03045(12) 0.5037(3) 0.1283(2) 0.0193(8) Uani d . 1 . .
O O1 0.06741(10) 0.7013(3) 0.25796(16) 0.0227(7) Uani d . 1 . .
O O2 0.07571(10) 0.7678(3) 0.10485(16) 0.0206(7) Uani d . 1 . .
O O3 0.14882(9) 0.6873(3) 0.21444(17) 0.0253(7) Uani d . 1 . .
O O4 0.10989(9) 0.4413(3) 0.24516(16) 0.0215(7) Uani d . 1 . .
C C1 0.22491(15) 0.4979(4) 0.0144(3) 0.0268(11) Uani d . 1 . .
C C2 0.20348(15) 0.3757(5) 0.0139(3) 0.0318(12) Uani d . 1 . .
H H2 0.2157 0.2965 -0.0018 0.038 Uiso calc R 1 . .
C C3 0.16424(15) 0.3716(4) 0.0365(3) 0.0269(11) Uani d . 1 . .
H H3 0.1497 0.2885 0.0375 0.032 Uiso calc R 1 . .
C C4 0.14579(14) 0.4876(4) 0.0578(3) 0.0197(10) Uani d . 1 . .
C C5 0.16748(15) 0.6093(4) 0.0566(3) 0.0257(11) Uani d . 1 . .
H H5 0.1549 0.6892 0.0707 0.031 Uiso calc R 1 . .
C C6 0.20726(14) 0.6144(4) 0.0351(3) 0.0236(10) Uani d . 1 . .
H H6 0.2221 0.6971 0.0347 0.028 Uiso calc R 1 . .
C C7 0.07464(14) 0.4036(4) 0.0519(3) 0.0222(10) Uani d . 1 . .
H H7 0.0788 0.3410 0.0139 0.027 Uiso calc R 1 . .
C C8 0.03340(13) 0.4058(4) 0.0765(2) 0.0168(9) Uani d . 1 . .
C C9 -0.00087(15) 0.3178(4) 0.0481(3) 0.0255(11) Uani d . 1 . .
H H9 0.0019 0.2505 0.0116 0.031 Uiso calc R 1 . .
C C10 -0.03943(15) 0.3295(4) 0.0736(3) 0.0261(11) Uani d . 1 . .
H H10 -0.0632 0.2691 0.0560 0.031 Uiso calc R 1 . .
C C11 -0.04250(15) 0.4301(5) 0.1249(3) 0.0265(11) Uani d . 1 . .
H H11 -0.0687 0.4407 0.1426 0.032 Uiso calc R 1 . .
C C12 -0.00710(14) 0.5167(4) 0.1508(3) 0.0223(10) Uani d . 1 . .
H H12 -0.0098 0.5870 0.1855 0.027 Uiso calc R 1 . .
C C13 0.07108(15) 0.8261(4) 0.2653(2) 0.0236(10) Uani d . 1 . .
C C14 0.06750(18) 0.8781(5) 0.3451(3) 0.0326(12) Uani d . 1 . .
C C15 0.07746(15) 0.9195(4) 0.2105(3) 0.0249(11) Uani d . 1 . .
H H15 0.0810 1.0110 0.2250 0.030 Uiso calc R 1 . .
C C16 0.07882(15) 0.8822(4) 0.1348(3) 0.0241(11) Uani d . 1 . .
C C17 0.08415(17) 0.9929(4) 0.0773(3) 0.0278(11) Uani d . 1 . .
C C18 0.18236(15) 0.6331(4) 0.2566(3) 0.0227(10) Uani d . 1 . .
C C19 0.22211(17) 0.7250(6) 0.2750(3) 0.0410(14) Uani d . 1 . .
C C20 0.18587(15) 0.5046(4) 0.2881(3) 0.0281(11) Uani d . 1 . .
H H20 0.2140 0.4740 0.3162 0.034 Uiso calc R 1 . .
C C21 0.14966(15) 0.4192(4) 0.2797(3) 0.0232(10) Uani d . 1 . .
C C22 0.15671(15) 0.2806(5) 0.3172(3) 0.0286(11) Uani d . 1 . .
F F1 0.11909(12) 0.9686(3) 0.0484(2) 0.0590(10) Uani d . 1 . .
F F2 0.04965(11) 0.9967(3) 0.01655(16) 0.0474(9) Uani d . 1 . .
F F3 0.08890(12) 1.1150(3) 0.10758(16) 0.0516(9) Uani d . 1 . .
F F4 0.03084(12) 0.8339(3) 0.3627(2) 0.0651(10) Uani d . 1 . .
F F5 0.06729(15) 1.0080(3) 0.35147(18) 0.0703(12) Uani d . 1 . .
F F6 0.09967(13) 0.8311(4) 0.40128(18) 0.0775(13) Uani d . 1 . .
F F7 0.22453(10) 0.8019(3) 0.2159(2) 0.0584(10) Uani d . 1 . .
F F8 0.21997(13) 0.8058(4) 0.3339(2) 0.0789(13) Uani d . 1 . .
F F9 0.26008(10) 0.6604(4) 0.2971(3) 0.0827(14) Uani d . 1 . .
F F10 0.13059(10) 0.2608(3) 0.3655(2) 0.0540(9) Uani d . 1 . .
F F11 0.19792(9) 0.2582(3) 0.35786(17) 0.0395(8) Uani d . 1 . .
F F12 0.14753(11) 0.1857(3) 0.26264(18) 0.0522(9) Uani d . 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'
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'
Ni Ni 0.3393 1.1124 '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'
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
O3 Ni1 O4 . . 89.27(12) ?
O3 Ni1 O2 . . 84.55(12) ?
O4 Ni1 O2 . . 173.82(12) ?
O3 Ni1 N2 . . 177.27(13) ?
O4 Ni1 N2 . . 89.36(12) ?
O2 Ni1 N2 . . 96.80(12) ?
O3 Ni1 O1 . . 87.79(12) ?
O4 Ni1 O1 . . 91.93(12) ?
O2 Ni1 O1 . . 87.99(12) ?
N2 Ni1 O1 . . 94.62(13) ?
O3 Ni1 N1 . . 98.24(13) ?
O4 Ni1 N1 . . 87.91(12) ?
O2 Ni1 N1 . . 92.82(12) ?
N2 Ni1 N1 . . 79.35(14) ?
O1 Ni1 N1 . . 173.97(13) ?
C7 N1 C4 . . 120.1(4) ?
C7 N1 Ni1 . . 111.8(3) ?
C4 N1 Ni1 . . 127.9(3) ?
C12 N2 C8 . . 118.6(4) ?
C12 N2 Ni1 . . 127.8(3) ?
C8 N2 Ni1 . . 113.2(3) ?
C13 O1 Ni1 . . 121.6(3) ?
C16 O2 Ni1 . . 121.2(3) ?
C18 O3 Ni1 . . 126.3(3) ?
C21 O4 Ni1 . . 124.0(3) ?
C6 C1 C2 . . 121.5(5) ?
C6 C1 Br1 . . 119.2(3) ?
C2 C1 Br1 . . 119.2(3) ?
C3 C2 C1 . . 118.9(4) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C2 C3 C4 . . 120.7(4) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.4(4) ?
C3 C4 N1 . . 122.4(4) ?
C5 C4 N1 . . 118.2(4) ?
C6 C5 C4 . . 120.5(4) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C1 C6 C5 . . 119.0(4) ?
C1 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
N1 C7 C8 . . 119.5(4) ?
N1 C7 H7 . . 120.3 ?
C8 C7 H7 . . 120.3 ?
N2 C8 C9 . . 122.1(4) ?
N2 C8 C7 . . 114.9(4) ?
C9 C8 C7 . . 123.0(4) ?
C8 C9 C10 . . 119.0(4) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C11 C10 C9 . . 118.7(4) ?
C11 C10 H10 . . 120.7 ?
C9 C10 H10 . . 120.7 ?
C10 C11 C12 . . 119.8(5) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
N2 C12 C11 . . 121.9(4) ?
N2 C12 H12 . . 119.1 ?
C11 C12 H12 . . 119.1 ?
O1 C13 C15 . . 128.3(4) ?
O1 C13 C14 . . 114.1(4) ?
C15 C13 C14 . . 117.7(4) ?
F5 C14 F6 . . 108.1(4) ?
F5 C14 F4 . . 106.8(5) ?
F6 C14 F4 . . 104.4(4) ?
F5 C14 C13 . . 114.9(4) ?
F6 C14 C13 . . 111.0(4) ?
F4 C14 C13 . . 111.0(4) ?
C13 C15 C16 . . 121.8(4) ?
C13 C15 H15 . . 119.1 ?
C16 C15 H15 . . 119.1 ?
O2 C16 C15 . . 129.0(4) ?
O2 C16 C17 . . 112.9(4) ?
C15 C16 C17 . . 118.1(4) ?
F2 C17 F3 . . 106.8(4) ?
F2 C17 F1 . . 106.0(4) ?
F3 C17 F1 . . 107.4(4) ?
F2 C17 C16 . . 111.0(4) ?
F3 C17 C16 . . 114.7(4) ?
F1 C17 C16 . . 110.5(4) ?
O3 C18 C20 . . 127.6(4) ?
O3 C18 C19 . . 112.9(4) ?
C20 C18 C19 . . 119.5(4) ?
F7 C19 F9 . . 107.5(5) ?
F7 C19 F8 . . 106.8(5) ?
F9 C19 F8 . . 106.1(5) ?
F7 C19 C18 . . 112.7(4) ?
F9 C19 C18 . . 113.3(4) ?
F8 C19 C18 . . 110.0(5) ?
C18 C20 C21 . . 122.6(4) ?
C18 C20 H20 . . 118.7 ?
C21 C20 H20 . . 118.7 ?
O4 C21 C20 . . 128.4(4) ?
O4 C21 C22 . . 112.9(4) ?
C20 C21 C22 . . 118.7(4) ?
F10 C22 F12 . . 107.4(4) ?
F10 C22 F11 . . 107.0(4) ?
F12 C22 F11 . . 106.3(4) ?
F10 C22 C21 . . 111.5(4) ?
F12 C22 C21 . . 110.5(4) ?
F11 C22 C21 . . 113.9(4) ?
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
Ni1 O3 . 2.020(3) y
Ni1 O4 . 2.044(3) y
Ni1 O2 . 2.045(3) y
Ni1 N2 . 2.063(3) y
Ni1 O1 . 2.066(3) y
Ni1 N1 . 2.113(4) y
Br1 C1 . 1.897(5) ?
N1 C7 . 1.291(5) ?
N1 C4 . 1.426(6) ?
N2 C12 . 1.332(6) ?
N2 C8 . 1.358(5) ?
O1 C13 . 1.258(5) ?
O2 C16 . 1.255(5) ?
O3 C18 . 1.253(5) ?
O4 C21 . 1.265(5) ?
C1 C6 . 1.376(6) ?
C1 C2 . 1.393(6) ?
C2 C3 . 1.379(6) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.388(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.396(6) ?
C5 C6 . 1.386(6) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.456(6) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.384(6) ?
C9 C10 . 1.390(7) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.372(6) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.393(6) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C15 . 1.394(6) ?
C13 C14 . 1.531(7) ?
C14 F5 . 1.304(5) ?
C14 F6 . 1.317(6) ?
C14 F4 . 1.332(6) ?
C15 C16 . 1.399(6) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.538(6) ?
C17 F2 . 1.326(5) ?
C17 F3 . 1.327(5) ?
C17 F1 . 1.334(6) ?
C18 C20 . 1.394(6) ?
C18 C19 . 1.517(7) ?
C19 F7 . 1.313(6) ?
C19 F9 . 1.325(6) ?
C19 F8 . 1.331(7) ?
C20 C21 . 1.397(6) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.529(6) ?
C22 F10 . 1.330(6) ?
C22 F12 . 1.333(5) ?
C22 F11 . 1.333(5) ?
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
C6 H6 Br1 7_565 0.95 3.015 3.870(3) 151 y
C2 H2 Br1 7_555 0.95 3.017 3.833(3) 145 y
C12 H12 O1 2_555 0.95 2.532 3.320(4) 140 y
C11 H11 O4 2_555 0.95 2.610 3.470(3) 151 y
