#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/68/2236816.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_2236816
loop_
_publ_author_name
'Souza, Marcela C. G.'
'da Ferreira, Leonardo'
'Comerlato, Nadia M.'
'Ferreira, Glaucio B.'
'do Visentin, Lorenzo'
_publ_section_title
;
 cis-Bis{(E)-2-[(2-fluorophenyl)iminomethyl]phenolato-κ²N,O}bis(pyridine-κN)nickel(II)
;
_journal_coeditor_code           BR2213
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1470
_journal_paper_doi               10.1107/S1600536812045576
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Ni (C13 H9 F N O)2 (C5 H5 N)2]'
_chemical_formula_moiety         'C36 H28 F2 N4 Ni O2'
_chemical_formula_sum            'C36 H28 F2 N4 Ni O2'
_chemical_formula_weight         645.32
_chemical_melting_point          569
_chemical_name_systematic
;
cis-Bis{(E)-2-[(2-fluorophenyl)iminomethyl]phenolato-
κ²N,O}bis(pyridine-κN)nickel(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.94(3)
_cell_angle_beta                 98.53(3)
_cell_angle_gamma                111.93(3)
_cell_formula_units_Z            1
_cell_length_a                   8.3160(17)
_cell_length_b                   10.344(2)
_cell_length_c                   11.049(2)
_cell_measurement_reflns_used    370
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     786.3(4)
_computing_cell_refinement       'PHICHI (Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ'
_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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11574
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.77
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  0.9242
_exptl_absorpt_correction_T_min  0.8950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.320
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0365
_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)+(0.0566P)²+0.3890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                2652
_reflns_number_total             2909
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            br2213.cif
_cod_data_source_block           I
_cod_original_cell_volume        786.2(3)
_cod_database_code               2236816
_cod_database_fobs_code          2236816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Ni Ni1 0.0000 0.0000 0.0000 0.04073(15) Uani d S 1 2
C C1 0.3568(3) 0.1876(2) -0.0377(2) 0.0434(5) Uani d . 1 1
C C2 0.4086(3) 0.3195(2) 0.0890(2) 0.0438(5) Uani d . 1 1
C C3 0.3036(3) 0.3221(2) 0.1802(2) 0.0419(5) Uani d . 1 1
C C4 0.3826(4) 0.4568(3) 0.3068(2) 0.0563(6) Uani d . 1 1
H H4 0.3208 0.4613 0.3706 0.068 Uiso calc R 1 1
C C5 0.5489(4) 0.5805(3) 0.3367(3) 0.0677(8) Uani d . 1 1
H H5 0.5966 0.6664 0.4200 0.081 Uiso calc R 1 1
C C6 0.6465(4) 0.5792(3) 0.2444(3) 0.0700(8) Uani d . 1 1
H H6 0.7565 0.6642 0.2644 0.084 Uiso calc R 1 1
C C7 0.5771(3) 0.4504(3) 0.1237(3) 0.0598(6) Uani d . 1 1
H H7 0.6427 0.4486 0.0624 0.072 Uiso calc R 1 1
C C8 0.1974(3) -0.0607(2) -0.2117(2) 0.0388(4) Uani d . 1 1
C C9 0.1232(3) -0.0664(3) -0.3351(2) 0.0513(5) Uani d . 1 1
C C10 0.0995(4) -0.1814(3) -0.4576(2) 0.0645(7) Uani d . 1 1
H H10 0.0511 -0.1816 -0.5392 0.077 Uiso calc R 1 1
C C11 0.1480(4) -0.2945(3) -0.4574(3) 0.0661(7) Uani d . 1 1
H H11 0.1311 -0.3727 -0.5389 0.079 Uiso calc R 1 1
C C12 0.2215(5) -0.2914(3) -0.3360(3) 0.0705(8) Uani d . 1 1
H H12 0.2560 -0.3671 -0.3356 0.085 Uiso calc R 1 1
C C13 0.2449(4) -0.1764(3) -0.2140(3) 0.0574(6) Uani d . 1 1
C C14 0.0620(5) -0.2436(3) 0.0879(3) 0.0752(8) Uani d . 1 1
H H14 -0.0445 -0.3115 0.0149 0.090 Uiso calc R 1 1
C C15 0.1386(6) -0.3036(4) 0.1603(4) 0.0860(10) Uani d . 1 1
H H15 0.0836 -0.4091 0.1363 0.103 Uiso calc R 1 1
C C16 0.2949(4) -0.2069(4) 0.2667(3) 0.0716(8) Uani d . 1 1
H H16 0.3489 -0.2448 0.3167 0.086 Uiso calc R 1 1
C C17 0.3709(4) -0.0527(4) 0.2986(3) 0.0793(9) Uani d . 1 1
H H17 0.4783 0.0167 0.3704 0.095 Uiso calc R 1 1
C C18 0.2847(4) -0.0020(3) 0.2217(3) 0.0674(7) Uani d . 1 1
H H18 0.3368 0.1034 0.2450 0.081 Uiso calc R 1 1
N N1 0.2146(2) 0.05438(19) -0.08618(16) 0.0381(4) Uani d . 1 1
N N2 0.1329(2) -0.0937(2) 0.11714(19) 0.0463(4) Uani d . 1 1
O O1 0.1449(2) 0.21035(17) 0.15535(15) 0.0486(4) Uani d . 1 1
H H1 0.438(4) 0.204(3) -0.085(3) 0.060(7) Uiso d . 1 1
F F1 0.0721(4) 0.0386(3) -0.3371(2) 0.0771(9) Uani d P 0.700(4) 1
F F1' 0.2941(10) -0.1824(8) -0.1059(5) 0.086(2) Uani d P 0.300(4) 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3390 1.1120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
O1 Ni1 N1 . . 88.26(7) n
O1 Ni1 N1 2 . 91.74(7) ?
O1 Ni1 N1 . 2 91.74(7) ?
O1 Ni1 N1 2 2 88.26(7) ?
O1 Ni1 N2 . . 89.03(7) ?
O1 Ni1 N2 2 . 90.97(7) ?
N1 Ni1 N2 . . 91.69(7) n
N1 Ni1 N2 2 . 88.31(7) ?
O1 Ni1 N2 . 2 90.97(7) ?
O1 Ni1 N2 2 2 89.03(7) ?
N1 Ni1 N2 . 2 88.31(7) ?
N1 Ni1 N2 2 2 91.69(7) ?
C3 O1 Ni1 . . 131.30(10) ?
C1 N1 C8 . . 116.6(2) ?
C1 N1 Ni1 . . 125.0(2) ?
C8 N1 Ni1 . . 118.30(10) ?
C18 N2 C14 . . 115.9(2) ?
C18 N2 Ni1 . . 121.7(2) ?
C14 N2 Ni1 . . 122.3(2) ?
C9 C8 C13 . . 117.5(2) ?
C9 C8 N1 . . 121.6(2) ?
C13 C8 N1 . . 120.9(2) ?
N1 C1 C2 . . 127.1(2) ?
N1 C1 H1 . . 120.(2) ?
C2 C1 H1 . . 113.(2) ?
O1 C3 C2 . . 124.2(2) ?
O1 C3 C4 . . 119.2(2) ?
C2 C3 C4 . . 116.6(2) ?
C7 C2 C3 . . 119.6(2) ?
C7 C2 C1 . . 116.6(2) ?
C3 C2 C1 . . 123.8(2) ?
F1 C9 C8 . . 119.2(2) ?
F1 C9 C10 . . 118.9(2) ?
C8 C9 C10 . . 121.9(2) ?
F1' C13 C8 . . 118.5(3) ?
F1' C13 C12 . . 120.4(3) ?
C8 C13 C12 . . 120.9(2) ?
C4 C5 C6 . . 121.4(2) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C5 C4 C3 . . 121.5(3) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C11 C12 C13 . . 120.6(3) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C11 C10 C9 . . 119.6(2) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
N2 C18 C17 . . 124.2(3) ?
N2 C18 H18 . . 117.9 ?
C17 C18 H18 . . 117.9 ?
C10 C11 C12 . . 119.5(2) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C6 C7 C2 . . 122.2(3) ?
C6 C7 H7 . . 118.9 ?
C2 C7 H7 . . 118.9 ?
C7 C6 C5 . . 118.7(2) ?
C7 C6 H6 . . 120.7 ?
C5 C6 H6 . . 120.7 ?
N2 C14 C15 . . 123.4(3) ?
N2 C14 H14 . . 118.3 ?
C15 C14 H14 . . 118.3 ?
C15 C16 C17 . . 118.4(3) ?
C15 C16 H16 . . 120.8 ?
C17 C16 H16 . . 120.8 ?
C16 C17 C18 . . 118.6(3) ?
C16 C17 H17 . . 120.7 ?
C18 C17 H17 . . 120.7 ?
C16 C15 C14 . . 119.4(3) ?
C16 C15 H15 . . 120.3 ?
C14 C15 H15 . . 120.3 ?
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
N1 Ni1 . 2.128(2) n
N2 Ni1 . 2.251(2) n
Ni1 O1 2 2.003(2) ?
Ni1 O1 . 2.003(2) n
Ni1 N1 2 2.128(2) ?
Ni1 N2 2 2.251(2) ?
C1 N1 . 1.294(3) n
C1 C2 . 1.444(3) ?
C1 H1 . 0.92(3) ?
C2 C7 . 1.419(3) ?
C2 C3 . 1.428(3) ?
C3 O1 . 1.300(3) ?
C3 C4 . 1.430(3) ?
C4 C5 . 1.384(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.394(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.368(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.382(3) ?
C8 C13 . 1.387(3) ?
C8 N1 . 1.431(3) n
C9 C10 . 1.390(3) ?
C10 C11 . 1.373(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.374(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.388(4) ?
C12 H12 . 0.9300 ?
C14 N2 . 1.333(3) ?
C14 C15 . 1.383(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.359(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.366(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.384(4) ?
C17 H17 . 0.9300 ?
C18 N2 . 1.324(3) ?
C18 H18 . 0.9300 ?
F1 C9 . 1.311(3) ?
F1' C13 . 1.234(5) ?
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
_geom_torsion_publ_flag
C8 N1 C1 C2 -177.3(2) n
