#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/26/4342653.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_4342653
loop_
_publ_author_name
'Reineke, Mark H.'
'Sampson, Matthew D.'
'Rheingold, Arnold L.'
'Kubiak, Clifford P.'
_publ_section_title
;
 Synthesis and Structural Studies of Nickel(0) Tetracarbene Complexes with
 the Introduction of a New Four-Coordinate Geometric Index, τδ.
;
_journal_issue                   7
_journal_name_full               'Inorganic chemistry'
_journal_page_first              3211
_journal_page_last               3217
_journal_paper_doi               10.1021/ic502792q
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C17 H16 N4 Ni0.5, F6 P'
_chemical_formula_sum            'C17 H16 F6 N4 Ni0.5 P'
_chemical_formula_weight         450.66
_chemical_name_systematic
;
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-05
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                109.690(2)
_cell_angle_beta                 101.917(2)
_cell_angle_gamma                106.568(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4116(4)
_cell_length_b                   9.9540(4)
_cell_length_c                   11.2819(4)
_cell_measurement_reflns_used    5023
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.934
_cell_measurement_theta_min      4.418
_cell_volume                     898.60(7)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'CU K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12959
_diffrn_reflns_theta_full        68.16
_diffrn_reflns_theta_max         68.16
_diffrn_reflns_theta_min         4.42
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    2.555
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0715 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.8436.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       thick_needles
_exptl_crystal_F_000             458
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .05
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0395
_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)+(0.0484P)²+0.9521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                2698
_reflns_number_total             3152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic502792q_si_002.cif
_cod_data_source_block           mhr_7_29_benz_0m
_cod_depositor_comments
'Adding full bibliography for 4342652--4342655.cif.'
_cod_original_cell_volume        898.60(6)
_cod_original_formula_sum        'C17 H16 F6 N4 Ni0.50 P'
_cod_database_code               4342653
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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 0.0000 0.0000 1.0000 0.02489(17) Uani 1 2 d S
P1 P -0.25635(9) 0.39747(8) 0.63121(7) 0.0353(2) Uani 1 1 d .
F1 F -0.1684(3) 0.3848(3) 0.52350(18) 0.0715(7) Uani 1 1 d .
F2 F -0.0871(2) 0.5080(2) 0.74569(16) 0.0473(4) Uani 1 1 d .
F3 F -0.2246(3) 0.2537(2) 0.6462(2) 0.0694(6) Uani 1 1 d .
F4 F -0.3405(3) 0.4092(3) 0.7400(2) 0.0638(6) Uani 1 1 d .
F5 F -0.2786(3) 0.5455(3) 0.6218(3) 0.0790(7) Uani 1 1 d .
F6 F -0.4179(3) 0.2887(3) 0.5171(2) 0.0867(8) Uani 1 1 d .
N1 N 0.0803(2) -0.0184(2) 0.76516(19) 0.0234(4) Uani 1 1 d .
N2 N 0.0658(2) 0.2034(2) 0.85724(19) 0.0238(4) Uani 1 1 d .
N3 N 0.1794(2) -0.1532(2) 0.87398(19) 0.0249(4) Uani 1 1 d .
N4 N 0.2808(3) -0.0739(2) 1.0872(2) 0.0279(5) Uani 1 1 d .
C1 C 0.0461(3) 0.0690(3) 0.8683(2) 0.0253(5) Uani 1 1 d .
C2 C 0.1300(3) 0.0620(3) 0.6917(2) 0.0236(5) Uani 1 1 d .
C3 C 0.1171(3) 0.2031(3) 0.7489(2) 0.0238(5) Uani 1 1 d .
C4 C 0.1585(3) 0.3161(3) 0.7028(3) 0.0307(6) Uani 1 1 d .
H4 H 0.1463 0.4092 0.7391 0.037 Uiso 1 1 calc R
C5 C 0.2192(3) 0.2825(3) 0.5995(3) 0.0362(6) Uani 1 1 d .
H5 H 0.2500 0.3557 0.5662 0.043 Uiso 1 1 calc R
C6 C 0.2352(3) 0.1423(3) 0.5444(2) 0.0346(6) Uani 1 1 d .
H6 H 0.2785 0.1253 0.4764 0.041 Uiso 1 1 calc R
C7 C 0.1888(3) 0.0270(3) 0.5872(2) 0.0287(5) Uani 1 1 d .
H7 H 0.1967 -0.0679 0.5484 0.034 Uiso 1 1 calc R
C8 C 0.0527(3) 0.3394(3) 0.9495(2) 0.0308(6) Uani 1 1 d .
H8A H 0.1456 0.4290 0.9749 0.046 Uiso 1 1 calc R
H8B H 0.0416 0.3252 1.0276 0.046 Uiso 1 1 calc R
H8C H -0.0378 0.3535 0.9067 0.046 Uiso 1 1 calc R
C9 C 0.0802(3) -0.1696(3) 0.7476(2) 0.0272(5) Uani 1 1 d .
H9A H 0.1212 -0.2081 0.6768 0.033 Uiso 1 1 calc R
H9B H -0.0261 -0.2421 0.7239 0.033 Uiso 1 1 calc R
C10 C 0.3002(3) -0.2068(3) 0.8909(2) 0.0260(5) Uani 1 1 d .
C11 C 0.3628(3) -0.1582(3) 1.0284(2) 0.0280(5) Uani 1 1 d .
C12 C 0.1657(3) -0.0738(3) 0.9929(2) 0.0257(5) Uani 1 1 d .
C13 C 0.3210(3) 0.0077(3) 1.2316(2) 0.0351(6) Uani 1 1 d .
H13A H 0.4329 0.0626 1.2720 0.053 Uiso 1 1 calc R
H13B H 0.2863 -0.0656 1.2676 0.053 Uiso 1 1 calc R
H13C H 0.2701 0.0796 1.2500 0.053 Uiso 1 1 calc R
C14 C 0.4832(3) -0.1974(3) 1.0830(3) 0.0369(6) Uani 1 1 d .
H14 H 0.5243 -0.1669 1.1745 0.044 Uiso 1 1 calc R
C15 C 0.5383(3) -0.2842(4) 0.9937(3) 0.0410(7) Uani 1 1 d .
H15 H 0.6173 -0.3143 1.0261 0.049 Uiso 1 1 calc R
C16 C 0.4788(3) -0.3281(3) 0.8559(3) 0.0371(6) Uani 1 1 d .
H16 H 0.5217 -0.3834 0.7997 0.044 Uiso 1 1 calc R
C17 C 0.3577(3) -0.2911(3) 0.8017(3) 0.0304(6) Uani 1 1 d .
H17 H 0.3170 -0.3211 0.7102 0.036 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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C1 Ni1 C1 180.00(16) . 2_557
C12 Ni1 C1 86.64(10) . .
C12 Ni1 C1 93.36(10) 2_557 .
C12 Ni1 C1 93.37(10) . 2_557
C12 Ni1 C1 86.63(10) 2_557 2_557
C12 Ni1 C12 180.00(16) 2_557 .
F1 P1 F2 87.97(11) . .
F1 P1 F3 89.15(13) . .
F3 P1 F2 87.77(12) . .
F4 P1 F1 178.66(13) . .
F4 P1 F2 91.14(12) . .
F4 P1 F3 89.81(12) . .
F5 P1 F1 90.46(14) . .
F5 P1 F2 89.19(12) . .
F5 P1 F3 176.95(14) . .
F5 P1 F4 90.53(13) . .
F6 P1 F1 90.35(12) . .
F6 P1 F2 178.27(13) . .
F6 P1 F3 91.79(15) . .
F6 P1 F4 90.54(13) . .
F6 P1 F5 91.24(15) . .
C1 N1 C2 111.7(2) . .
C1 N1 C9 121.91(19) . .
C2 N1 C9 126.0(2) . .
C1 N2 C3 110.5(2) . .
C1 N2 C8 126.8(2) . .
C3 N2 C8 122.5(2) . .
C10 N3 C9 126.5(2) . .
C12 N3 C9 121.6(2) . .
C12 N3 C10 111.9(2) . .
C11 N4 C13 123.5(2) . .
C12 N4 C11 110.8(2) . .
C12 N4 C13 125.7(2) . .
N1 C1 Ni1 121.38(17) . .
N2 C1 Ni1 132.72(18) . .
N2 C1 N1 105.7(2) . .
C3 C2 N1 105.2(2) . .
C7 C2 N1 132.6(2) . .
C7 C2 C3 122.1(2) . .
C2 C3 N2 106.8(2) . .
C4 C3 N2 131.2(2) . .
C4 C3 C2 121.9(2) . .
C3 C4 H4 121.9 . .
C5 C4 C3 116.2(2) . .
C5 C4 H4 121.9 . .
C4 C5 H5 119.2 . .
C4 C5 C6 121.7(2) . .
C6 C5 H5 119.2 . .
C5 C6 H6 118.9 . .
C7 C6 C5 122.3(2) . .
C7 C6 H6 118.9 . .
C2 C7 H7 122.1 . .
C6 C7 C2 115.8(2) . .
C6 C7 H7 122.1 . .
N2 C8 H8A 109.5 . .
N2 C8 H8B 109.5 . .
N2 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N1 C9 N3 107.70(19) . .
N1 C9 H9A 110.2 . .
N1 C9 H9B 110.2 . .
N3 C9 H9A 110.2 . .
N3 C9 H9B 110.2 . .
H9A C9 H9B 108.5 . .
N3 C10 C11 105.0(2) . .
C17 C10 N3 132.8(2) . .
C17 C10 C11 122.2(2) . .
C10 C11 N4 106.9(2) . .
C10 C11 C14 121.3(2) . .
C14 C11 N4 131.8(2) . .
N3 C12 Ni1 121.23(18) . .
N4 C12 Ni1 133.24(18) . .
N4 C12 N3 105.4(2) . .
N4 C13 H13A 109.5 . .
N4 C13 H13B 109.5 . .
N4 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 H14 121.8 . .
C15 C14 C11 116.4(3) . .
C15 C14 H14 121.8 . .
C14 C15 H15 119.0 . .
C14 C15 C16 122.1(3) . .
C16 C15 H15 119.0 . .
C15 C16 H16 119.3 . .
C17 C16 C15 121.5(3) . .
C17 C16 H16 119.3 . .
C10 C17 H17 121.7 . .
C16 C17 C10 116.5(2) . .
C16 C17 H17 121.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.911(2) .
Ni1 C1 1.911(2) 2_557
Ni1 C12 1.909(3) .
Ni1 C12 1.909(3) 2_557
P1 F1 1.5964(19) .
P1 F2 1.6151(19) .
P1 F3 1.597(2) .
P1 F4 1.5827(19) .
P1 F5 1.581(2) .
P1 F6 1.567(2) .
N1 C1 1.359(3) .
N1 C2 1.392(3) .
N1 C9 1.450(3) .
N2 C1 1.349(3) .
N2 C3 1.403(3) .
N2 C8 1.459(3) .
N3 C9 1.462(3) .
N3 C10 1.392(3) .
N3 C12 1.362(3) .
N4 C11 1.395(3) .
N4 C12 1.352(3) .
N4 C13 1.461(3) .
C2 C3 1.387(3) .
C2 C7 1.385(3) .
C3 C4 1.385(3) .
C4 H4 0.9300 .
C4 C5 1.384(4) .
C5 H5 0.9300 .
C5 C6 1.390(4) .
C6 H6 0.9300 .
C6 C7 1.384(4) .
C7 H7 0.9300 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.393(3) .
C10 C17 1.388(4) .
C11 C14 1.394(4) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14 0.9300 .
C14 C15 1.384(4) .
C15 H15 0.9300 .
C15 C16 1.401(4) .
C16 H16 0.9300 .
C16 C17 1.383(4) .
C17 H17 0.9300 .
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_site_symmetry_1
N1 C2 C3 N2 2.1(3) .
N1 C2 C3 C4 179.2(2) .
N1 C2 C7 C6 -176.2(3) .
N2 C3 C4 C5 173.9(3) .
N3 C10 C11 N4 -2.0(3) .
N3 C10 C11 C14 177.1(2) .
N3 C10 C17 C16 -178.0(3) .
N4 C11 C14 C15 179.9(3) .
C1 Ni1 C1 N1 -151(20) 2_557
C1 Ni1 C1 N2 36(20) 2_557
C1 Ni1 C12 N3 135.1(2) 2_557
C1 Ni1 C12 N3 -44.9(2) .
C1 Ni1 C12 N4 139.9(3) .
C1 Ni1 C12 N4 -40.1(3) 2_557
C1 N1 C2 C3 -3.4(3) .
C1 N1 C2 C7 173.8(3) .
C1 N1 C9 N3 -51.9(3) .
C1 N2 C3 C2 -0.3(3) .
C1 N2 C3 C4 -177.0(3) .
C2 N1 C1 Ni1 -172.14(17) .
C2 N1 C1 N2 3.2(3) .
C2 N1 C9 N3 120.7(2) .
C2 C3 C4 C5 -2.4(4) .
C3 N2 C1 Ni1 172.84(19) .
C3 N2 C1 N1 -1.7(3) .
C3 C2 C7 C6 0.6(4) .
C3 C4 C5 C6 0.9(4) .
C4 C5 C6 C7 1.3(4) .
C5 C6 C7 C2 -2.0(4) .
C7 C2 C3 N2 -175.4(2) .
C7 C2 C3 C4 1.7(4) .
C8 N2 C1 Ni1 -1.3(4) .
C8 N2 C1 N1 -175.9(2) .
C8 N2 C3 C2 174.2(2) .
C8 N2 C3 C4 -2.5(4) .
C9 N1 C1 Ni1 1.4(3) .
C9 N1 C1 N2 176.7(2) .
C9 N1 C2 C3 -176.6(2) .
C9 N1 C2 C7 0.6(4) .
C9 N3 C10 C11 177.7(2) .
C9 N3 C10 C17 -2.7(4) .
C9 N3 C12 Ni1 7.4(3) .
C9 N3 C12 N4 -176.2(2) .
C10 N3 C9 N1 -130.0(2) .
C10 N3 C12 Ni1 -175.23(16) .
C10 N3 C12 N4 1.2(3) .
C10 C11 C14 C15 1.2(4) .
C11 N4 C12 Ni1 173.34(19) .
C11 N4 C12 N3 -2.5(3) .
C11 C10 C17 C16 1.5(4) .
C11 C14 C15 C16 1.2(4) .
C12 Ni1 C1 N1 -139.4(2) 2_557
C12 Ni1 C1 N1 40.6(2) .
C12 Ni1 C1 N2 46.7(3) 2_557
C12 Ni1 C1 N2 -133.3(3) .
C12 Ni1 C12 N3 58(21) 2_557
C12 Ni1 C12 N4 -117(21) 2_557
C12 N3 C9 N1 46.9(3) .
C12 N3 C10 C11 0.5(3) .
C12 N3 C10 C17 -179.9(3) .
C12 N4 C11 C10 2.8(3) .
C12 N4 C11 C14 -176.0(3) .
C13 N4 C11 C10 -174.7(2) .
C13 N4 C11 C14 6.4(4) .
C13 N4 C12 Ni1 -9.2(4) .
C13 N4 C12 N3 175.0(2) .
C14 C15 C16 C17 -2.2(5) .
C15 C16 C17 C10 0.8(4) .
C17 C10 C11 N4 178.4(2) .
C17 C10 C11 C14 -2.6(4) .
