#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:43:03 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179489 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/86/4338699.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4338699
loop_
_publ_author_name
'Gushchin, Pavel V.'
'Luzyanin, Konstantin V.'
'Kopylovich, Maximilian N.'
'Haukka, Matti'
'Pombeiro, Armando J. L.'
'Kukushkin, Vadim Yu'
_publ_section_title
;
 NiII-mediated coupling between iminoisoindolinones and nitriles leading
 to unsymmetrical 1,3,5-triazapentadienato complexes.
;
_journal_issue                   8
_journal_name_full               'Inorganic chemistry'
_journal_page_first              3088
_journal_page_last               3094
_journal_paper_doi               10.1021/ic702131k
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C22 H12 F8 N6 Ni O2'
_chemical_formula_sum            'C22 H12 F8 N6 Ni O2'
_chemical_formula_weight         603.09
_chemical_name_systematic
;
 ?
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.583(5)
_cell_angle_beta                 102.770(6)
_cell_angle_gamma                100.797(6)
_cell_formula_units_Z            1
_cell_length_a                   5.6247(5)
_cell_length_b                   8.8801(11)
_cell_length_c                   11.1999(11)
_cell_measurement_reflns_used    12365
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     520.92(10)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Diamond v.3.1d (Brandenburg, 2006)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9081
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    1.041
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_correction_T_min  0.8429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2377
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0452
_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)+(0.0388P)²+0.2256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                1665
_reflns_number_total             2377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            all.cif
_cod_data_source_block           16
_cod_database_code               4338699
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni1 Ni 1.0000 0.0000 0.0000 0.03127(19) Uani 1 2 d S
F1 F 0.5801(3) 0.2403(2) 0.42919(15) 0.0425(5) Uani 1 1 d .
F2 F 0.2559(3) 0.4295(2) 0.41151(15) 0.0421(5) Uani 1 1 d .
F3 F 0.0946(3) 0.5166(2) 0.19761(16) 0.0415(5) Uani 1 1 d .
F4 F 0.2508(3) 0.4178(2) -0.00906(15) 0.0385(4) Uani 1 1 d .
O1 O 0.5965(4) 0.2270(3) -0.09437(18) 0.0372(5) Uani 1 1 d .
N1 N 1.0676(5) -0.0684(3) 0.1472(2) 0.0324(6) Uani 1 1 d D
H1 H 1.168(5) -0.132(3) 0.154(3) 0.032(9) Uiso 1 1 d D
N2 N 0.8590(5) 0.0648(3) 0.2785(2) 0.0336(6) Uani 1 1 d .
N3 N 0.7854(4) 0.1191(3) 0.0694(2) 0.0304(6) Uani 1 1 d .
C1 C 1.0036(5) -0.0390(4) 0.2518(3) 0.0333(7) Uani 1 1 d .
C2 C 1.0792(6) -0.1236(4) 0.3544(3) 0.0386(8) Uani 1 1 d .
H2A H 1.1518 -0.0458 0.4362 0.046 Uiso 1 1 calc R
H2B H 1.2092 -0.1790 0.3364 0.046 Uiso 1 1 calc R
C3 C 0.8535(6) -0.2422(4) 0.3626(3) 0.0463(9) Uani 1 1 d .
H3A H 0.7262 -0.1871 0.3819 0.070 Uiso 1 1 calc R
H3B H 0.9062 -0.2961 0.4292 0.070 Uiso 1 1 calc R
H3C H 0.7829 -0.3199 0.2818 0.070 Uiso 1 1 calc R
C4 C 0.7639(5) 0.1309(4) 0.1915(3) 0.0304(7) Uani 1 1 d .
C5 C 0.5973(5) 0.2374(4) 0.2169(3) 0.0314(7) Uani 1 1 d .
C6 C 0.5136(6) 0.2864(4) 0.3214(3) 0.0344(7) Uani 1 1 d .
C7 C 0.3450(6) 0.3819(4) 0.3127(3) 0.0341(7) Uani 1 1 d .
C8 C 0.2623(5) 0.4278(4) 0.2031(3) 0.0350(7) Uani 1 1 d .
C9 C 0.3446(6) 0.3775(4) 0.0979(3) 0.0327(7) Uani 1 1 d .
C10 C 0.5133(5) 0.2845(4) 0.1075(3) 0.0312(7) Uani 1 1 d .
C11 C 0.6314(5) 0.2098(4) 0.0130(3) 0.0324(7) Uani 1 1 d .
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N1 180.0 . 2_755 ?
N1 Ni1 N3 91.71(10) . 2_755 ?
N1 Ni1 N3 88.30(10) 2_755 2_755 ?
N1 Ni1 N3 88.29(10) . . yes
N1 Ni1 N3 91.70(10) 2_755 . ?
N3 Ni1 N3 180.0 2_755 . ?
C1 N1 Ni1 133.9(2) . . yes
C1 N1 H1 108(2) . . ?
Ni1 N1 H1 118(2) . . ?
C4 N2 C1 118.9(2) . . yes
C4 N3 C11 107.3(2) . . ?
C4 N3 Ni1 123.16(19) . . ?
C11 N3 Ni1 129.50(19) . . ?
N1 C1 N2 124.5(3) . . yes
N1 C1 C2 121.1(3) . . ?
N2 C1 C2 114.4(2) . . ?
C1 C2 C3 110.6(3) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 N3 130.9(3) . . yes
N2 C4 C5 119.5(2) . . ?
N3 C4 C5 109.6(2) . . ?
C10 C5 C6 119.9(3) . . ?
C10 C5 C4 107.5(2) . . ?
C6 C5 C4 132.6(3) . . ?
F1 C6 C5 123.0(3) . . ?
F1 C6 C7 118.5(3) . . ?
C5 C6 C7 118.4(3) . . ?
F2 C7 C8 118.7(3) . . ?
F2 C7 C6 120.2(3) . . ?
C8 C7 C6 121.1(3) . . ?
F3 C8 C7 119.2(3) . . ?
F3 C8 C9 120.3(3) . . ?
C7 C8 C9 120.4(3) . . ?
F4 C9 C10 122.9(3) . . ?
F4 C9 C8 118.9(3) . . ?
C10 C9 C8 118.1(3) . . ?
C9 C10 C5 121.9(3) . . ?
C9 C10 C11 131.2(3) . . ?
C5 C10 C11 106.8(3) . . ?
O1 C11 N3 127.3(3) . . ?
O1 C11 C10 123.9(3) . . ?
N3 C11 C10 108.8(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 1.846(2) . yes
Ni1 N1 1.846(2) 2_755 ?
Ni1 N3 1.942(2) 2_755 ?
Ni1 N3 1.942(2) . yes
F1 C6 1.343(3) . ?
F2 C7 1.345(3) . ?
F3 C8 1.337(3) . ?
F4 C9 1.337(3) . ?
O1 C11 1.217(3) . ?
N1 C1 1.296(4) . yes
N1 H1 0.874(10) . ?
N2 C4 1.295(4) . ?
N2 C1 1.374(4) . yes
N3 C4 1.387(3) . yes
N3 C11 1.415(4) . yes
C1 C2 1.512(4) . ?
C2 C3 1.521(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.484(4) . yes
C5 C10 1.380(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.385(4) . ?
C7 C8 1.375(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.370(4) . ?
C10 C11 1.491(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.874(10) 1.872(18) 2.662(3) 149(3) 2_755
