#------------------------------------------------------------------------------
#$Date: 2017-09-01 18:34:00 +0300 (Fri, 01 Sep 2017) $
#$Revision: 200072 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/26/4032690.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_4032690
loop_
_publ_author_name
'Ashwin G. Nair'
'Roy T. McBurney'
'Mark R.D. Gatus'
'D.Barney Walker'
'Mohan Bhadbhade'
'Barbara A. Messerle'
_publ_section_title
;
 Synthesis and catalytic activity of nickel(II) complexes containing NCN
 pincer ligands
;
_journal_name_full               'Journal of Organometallic Chemistry'
_journal_page_first              63
_journal_page_last               70
_journal_paper_doi               10.1016/j.jorganchem.2017.02.025
_journal_volume                  845
_journal_year                    2017
_chemical_formula_moiety         'C11 H12 Cl N6 Ni, F6 P'
_chemical_formula_sum            'C11 H12 Cl F6 N6 Ni P'
_chemical_formula_weight         467.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                91.69(3)
_cell_angle_beta                 104.13(3)
_cell_angle_gamma                104.66(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9770(16)
_cell_length_b                   8.7170(17)
_cell_length_c                   12.200(2)
_cell_measurement_reflns_used    4992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      2.5
_cell_measurement_theta_min      22.5
_cell_volume                     792.1(3)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.925
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16062
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.056
_diffrn_reflns_theta_min         1.729
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.570
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0525P)²+0.9530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3991
_reflns_number_total             4211
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Org-Chem-2017-845-63-70-3.cif
_cod_data_source_block           3
_cod_database_code               4032690
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id Ni_2a
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni01 Ni 0.46725(3) 0.34531(3) 0.61665(2) 0.01227(8) Uani 1 1 d . . . . .
Cl01 Cl 0.29656(7) 0.32490(5) 0.44054(4) 0.01750(11) Uani 1 1 d . . . . .
P01 P 0.21480(8) 0.08072(6) 0.87872(4) 0.01525(11) Uani 1 1 d . . . . .
F02 F 0.3691(2) 0.24517(16) 0.91955(11) 0.0238(3) Uani 1 1 d . . . . .
F01 F 0.2178(2) 0.10385(19) 0.74959(11) 0.0292(3) Uani 1 1 d . . . . .
F03 F 0.0664(2) 0.1767(2) 0.86836(15) 0.0351(4) Uani 1 1 d . . . . .
F05 F 0.3659(2) -0.0131(2) 0.88911(15) 0.0338(4) Uani 1 1 d . . . . .
F06 F 0.2143(2) 0.0566(2) 1.00835(12) 0.0327(4) Uani 1 1 d . . . . .
F04 F 0.0594(2) -0.08224(18) 0.83832(13) 0.0320(3) Uani 1 1 d . . . . .
N06 N 0.3295(3) 0.4660(2) 0.66927(14) 0.0172(3) Uani 1 1 d . . . . .
N03 N 0.6914(2) 0.2616(2) 0.81574(13) 0.0144(3) Uani 1 1 d . . . . .
N01 N 0.6037(2) 0.21556(19) 0.57353(14) 0.0147(3) Uani 1 1 d . . . . .
N02 N 0.7002(2) 0.13365(19) 0.64577(14) 0.0143(3) Uani 1 1 d . . . . .
N05 N 0.3951(3) 0.5768(2) 0.76135(14) 0.0189(4) Uani 1 1 d . . . . .
N04 N 0.6507(3) 0.4906(2) 0.84277(14) 0.0158(3) Uani 1 1 d . . . . .
C02 C 0.7837(3) 0.3182(2) 0.92752(16) 0.0172(4) Uani 1 1 d . . . . .
H02 H 0.8511 0.2652 0.9811 0.021 Uiso 1 1 calc R . . . .
C11 C 0.6540(3) 0.2064(2) 0.47667(16) 0.0171(4) Uani 1 1 d . . . . .
H11 H 0.6108 0.2546 0.4106 0.021 Uiso 1 1 calc R . . . .
C01 C 0.6089(3) 0.3663(2) 0.76362(16) 0.0146(3) Uani 1 1 d . . . . .
C08 C 0.1538(3) 0.4516(3) 0.63603(19) 0.0214(4) Uani 1 1 d . . . . .
H08 H 0.0723 0.3810 0.5741 0.026 Uiso 1 1 calc R . . . .
C05 C 0.6684(3) 0.1075(2) 0.75673(16) 0.0153(4) Uani 1 1 d . . . . .
H05A H 0.7544 0.0531 0.8004 0.018 Uiso 1 1 calc R . . . .
H05B H 0.5452 0.0395 0.7484 0.018 Uiso 1 1 calc R . . . .
C03 C 0.7583(3) 0.4640(3) 0.94474(16) 0.0183(4) Uani 1 1 d . . . . .
H03 H 0.8047 0.5340 1.0127 0.022 Uiso 1 1 calc R . . . .
C09 C 0.8043(3) 0.0721(2) 0.59519(17) 0.0166(4) Uani 1 1 d . . . . .
H09 H 0.8815 0.0095 0.6285 0.020 Uiso 1 1 calc R . . . .
C04 C 0.5850(3) 0.6300(2) 0.81648(17) 0.0197(4) Uani 1 1 d . . . . .
H04A H 0.6058 0.6988 0.8871 0.024 Uiso 1 1 calc R . . . .
H04B H 0.6496 0.6925 0.7657 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7782(3) 0.1168(2) 0.48607(17) 0.0192(4) Uani 1 1 d . . . . .
H10 H 0.8330 0.0919 0.4294 0.023 Uiso 1 1 calc R . . . .
C07 C 0.1061(4) 0.5553(3) 0.7052(2) 0.0276(5) Uani 1 1 d . . . . .
H07 H -0.0101 0.5689 0.6992 0.033 Uiso 1 1 calc R . . . .
C06 C 0.2624(4) 0.6329(3) 0.78345(19) 0.0258(5) Uani 1 1 d . . . . .
H06 H 0.2751 0.7118 0.8425 0.031 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.1484 0.1585 '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'
P P 0.1023 0.0942 '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
N06 Ni01 Cl01 90.68(6) . .
N01 Ni01 Cl01 92.31(6) . .
N01 Ni01 N06 175.68(7) . .
C01 Ni01 Cl01 178.86(6) . .
C01 Ni01 N06 88.40(9) . .
C01 Ni01 N01 88.64(9) . .
F01 P01 F02 90.07(9) . .
F01 P01 F05 89.28(10) . .
F01 P01 F06 179.19(10) . .
F01 P01 F04 90.11(9) . .
F03 P01 F02 89.48(9) . .
F03 P01 F01 90.45(10) . .
F03 P01 F05 179.13(10) . .
F03 P01 F06 90.34(10) . .
F03 P01 F04 89.93(10) . .
F05 P01 F02 89.69(9) . .
F06 P01 F02 89.78(8) . .
F06 P01 F05 89.92(10) . .
F04 P01 F02 179.38(9) . .
F04 P01 F05 90.91(10) . .
F04 P01 F06 90.05(9) . .
N05 N06 Ni01 124.19(15) . .
C08 N06 Ni01 129.52(16) . .
C08 N06 N05 105.91(18) . .
C02 N03 C05 128.28(17) . .
C01 N03 C02 111.48(17) . .
C01 N03 C05 120.13(16) . .
N02 N01 Ni01 124.85(13) . .
C11 N01 Ni01 129.10(14) . .
C11 N01 N02 105.00(17) . .
N01 N02 C05 120.12(17) . .
C09 N02 N01 111.42(16) . .
C09 N02 C05 128.07(17) . .
N06 N05 C04 121.40(18) . .
C06 N05 N06 110.6(2) . .
C06 N05 C04 127.8(2) . .
C01 N04 C03 111.41(17) . .
C01 N04 C04 120.60(17) . .
C03 N04 C04 127.99(17) . .
N03 C02 H02 126.9 . .
C03 C02 N03 106.29(18) . .
C03 C02 H02 126.9 . .
N01 C11 H11 124.5 . .
N01 C11 C10 110.98(18) . .
C10 C11 H11 124.5 . .
N03 C01 Ni01 128.01(15) . .
N03 C01 N04 104.72(16) . .
N04 C01 Ni01 127.27(15) . .
N06 C08 H08 124.8 . .
N06 C08 C07 110.4(2) . .
C07 C08 H08 124.8 . .
N03 C05 H05A 110.1 . .
N03 C05 H05B 110.1 . .
N02 C05 N03 108.05(15) . .
N02 C05 H05A 110.1 . .
N02 C05 H05B 110.1 . .
H05A C05 H05B 108.4 . .
N04 C03 H03 126.9 . .
C02 C03 N04 106.10(18) . .
C02 C03 H03 126.9 . .
N02 C09 H09 126.3 . .
N02 C09 C10 107.33(18) . .
C10 C09 H09 126.3 . .
N05 C04 N04 108.45(17) . .
N05 C04 H04A 110.0 . .
N05 C04 H04B 110.0 . .
N04 C04 H04A 110.0 . .
N04 C04 H04B 110.0 . .
H04A C04 H04B 108.4 . .
C11 C10 H10 127.4 . .
C09 C10 C11 105.26(18) . .
C09 C10 H10 127.4 . .
C08 C07 H07 127.2 . .
C06 C07 C08 105.5(2) . .
C06 C07 H07 127.2 . .
N05 C06 C07 107.6(2) . .
N05 C06 H06 126.2 . .
C07 C06 H06 126.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni01 Cl01 2.2199(9) .
Ni01 N06 1.9016(19) .
Ni01 N01 1.8996(18) .
Ni01 C01 1.847(2) .
P01 F02 1.6073(16) .
P01 F01 1.5993(15) .
P01 F03 1.5974(17) .
P01 F05 1.6032(17) .
P01 F06 1.6023(15) .
P01 F04 1.6017(17) .
N06 N05 1.364(2) .
N06 C08 1.333(3) .
N03 C02 1.390(2) .
N03 C01 1.344(3) .
N03 C05 1.453(3) .
N01 N02 1.365(2) .
N01 C11 1.344(3) .
N02 C05 1.451(2) .
N02 C09 1.347(3) .
N05 C04 1.446(3) .
N05 C06 1.351(3) .
N04 C01 1.347(2) .
N04 C03 1.391(3) .
N04 C04 1.455(3) .
C02 H02 0.9500 .
C02 C03 1.355(3) .
C11 H11 0.9500 .
C11 C10 1.395(3) .
C08 H08 0.9500 .
C08 C07 1.400(3) .
C05 H05A 0.9900 .
C05 H05B 0.9900 .
C03 H03 0.9500 .
C09 H09 0.9500 .
C09 C10 1.380(3) .
C04 H04A 0.9900 .
C04 H04B 0.9900 .
C10 H10 0.9500 .
C07 H07 0.9500 .
C07 C06 1.370(4) .
C06 H06 0.9500 .
