#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:05:44 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180168 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/64/7106484.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_7106484
loop_
_publ_author_name
'V. Sara Thoi'
'Christopher J. Chang'
_publ_section_title
;
 Nickel N-Heterocyclic Carbene-Pyridine Complexes that Exhibit High
 Selectivity for Electrocatalytic Reduction of Carbon Dioxide Over Water
;
_journal_name_full               Chem.Commun.
_journal_page_first              6578
_journal_paper_doi               10.1039/c1cc10449g
_journal_year                    2011
_chemical_formula_moiety         'C18 H16 F12 N6 Ni P2'
_chemical_formula_sum            'C18 H16 F12 N6 Ni P2'
_chemical_formula_weight         665.02
_chemical_name_systematic
;
?
;
_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                 100.4060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0790(7)
_cell_length_b                   19.0802(15)
_cell_length_c                   12.1281(9)
_cell_measurement_reflns_used    12779
_cell_measurement_temperature    119(2)
_cell_measurement_theta_max      25.333
_cell_measurement_theta_min      2.315
_cell_volume                     2294.0(3)
_computing_cell_refinement       'Bruker APEX2 v. 2009.3'
_computing_data_collection       'Bruker APEX2 v. 2009.3'
_computing_data_reduction        'Bruker APEX2 v. 2009.3'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      119(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0117
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12525
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    1.106
_exptl_absorpt_correction_T_max  0.8091
_exptl_absorpt_correction_T_min  0.7326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0271P)²+2.8738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                2061
_reflns_number_total             2099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10449g.txt
_cod_data_source_block           ethyl
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7106484
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.12364(15) 0.14192(8) 0.35626(13) 0.0205(3) Uani 1 1 d . . .
H1 H 0.0365 0.1212 0.3409 0.025 Uiso 1 1 calc R . .
C2 C 0.23065(17) 0.10245(9) 0.41080(13) 0.0237(3) Uani 1 1 d . . .
H2 H 0.2172 0.0555 0.4322 0.028 Uiso 1 1 calc R . .
C3 C 0.35767(16) 0.13246(9) 0.43373(13) 0.0251(4) Uani 1 1 d . . .
H3 H 0.4332 0.1055 0.4680 0.030 Uiso 1 1 calc R . .
C4 C 0.37423(16) 0.20216(9) 0.40643(13) 0.0228(3) Uani 1 1 d . . .
H4 H 0.4596 0.2245 0.4238 0.027 Uiso 1 1 calc R . .
C5 C 0.26183(15) 0.23745(8) 0.35314(12) 0.0182(3) Uani 1 1 d . . .
C8 C 0.13682(15) 0.33838(8) 0.28700(12) 0.0180(3) Uani 1 1 d . . .
C6 C 0.36134(17) 0.35891(9) 0.33908(14) 0.0249(3) Uani 1 1 d . . .
H7 H 0.4549 0.3515 0.3655 0.030 Uiso 1 1 calc R . .
C7 C 0.30014(17) 0.41975(9) 0.30596(14) 0.0261(4) Uani 1 1 d . . .
H8 H 0.3432 0.4639 0.3041 0.031 Uiso 1 1 calc R . .
C9 C 0.06461(17) 0.46030(8) 0.22610(13) 0.0237(3) Uani 1 1 d . . .
H9A H 0.0415 0.4527 0.1441 0.028 Uiso 1 1 calc R . .
H9B H 0.1074 0.5070 0.2387 0.028 Uiso 1 1 calc R . .
N1 N 0.13805(12) 0.20844(7) 0.32412(10) 0.0174(3) Uani 1 1 d . . .
N2 N 0.25934(13) 0.30914(7) 0.32668(10) 0.0191(3) Uani 1 1 d . . .
N3 N 0.16254(14) 0.40679(7) 0.27484(11) 0.0209(3) Uani 1 1 d . . .
F1 F -0.33319(11) 0.57640(6) 0.12981(9) 0.0352(3) Uani 1 1 d . . .
F2 F -0.15326(10) 0.54929(5) 0.04931(8) 0.0294(2) Uani 1 1 d . . .
F3 F -0.16128(11) 0.65299(6) 0.13973(9) 0.0379(3) Uani 1 1 d . . .
F4 F -0.18082(11) 0.65111(6) -0.04842(9) 0.0342(3) Uani 1 1 d . . .
F5 F -0.36362(10) 0.67751(5) 0.03045(9) 0.0324(2) Uani 1 1 d . . .
F6 F -0.35412(11) 0.57406(6) -0.05910(9) 0.0366(3) Uani 1 1 d . . .
P2 P -0.25765(4) 0.61448(2) 0.04006(3) 0.01976(11) Uani 1 1 d . . .
Ni1 Ni 0.0000 0.273491(14) 0.2500 0.01563(9) Uani 1 2 d S . .
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'
F F 0.0171 0.0103 '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'
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 C1 C2 122.53(15) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.96(15) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.69(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 117.20(15) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
N1 C5 C4 124.41(15) . . ?
N1 C5 N2 111.21(13) . . ?
C4 C5 N2 124.32(14) . . ?
N3 C8 N2 104.85(13) . . ?
N3 C8 Ni1 140.77(12) . . ?
N2 C8 Ni1 113.63(11) . . ?
C7 C6 N2 105.55(14) . . ?
C7 C6 H7 127.2 . . ?
N2 C6 H7 127.2 . . ?
C6 C7 N3 108.01(14) . . ?
C6 C7 H8 126.0 . . ?
N3 C7 H8 126.0 . . ?
N3 C9 C9 114.02(12) . 2 ?
N3 C9 H9A 108.7 . . ?
C9 C9 H9A 108.7 2 . ?
N3 C9 H9B 108.7 . . ?
C9 C9 H9B 108.7 2 . ?
H9A C9 H9B 107.6 . . ?
C1 N1 C5 117.02(13) . . ?
C1 N1 Ni1 128.84(11) . . ?
C5 N1 Ni1 113.94(10) . . ?
C8 N2 C6 111.40(13) . . ?
C8 N2 C5 117.24(13) . . ?
C6 N2 C5 131.26(13) . . ?
C8 N3 C7 110.20(14) . . ?
C8 N3 C9 126.20(13) . . ?
C7 N3 C9 123.37(13) . . ?
F3 P2 F4 90.28(6) . . ?
F3 P2 F5 90.92(6) . . ?
F4 P2 F5 91.17(6) . . ?
F3 P2 F6 178.77(7) . . ?
F4 P2 F6 90.49(6) . . ?
F5 P2 F6 90.03(6) . . ?
F3 P2 F1 89.61(6) . . ?
F4 P2 F1 178.97(6) . . ?
F5 P2 F1 89.85(6) . . ?
F6 P2 F1 89.61(6) . . ?
F3 P2 F2 90.13(6) . . ?
F4 P2 F2 89.71(6) . . ?
F5 P2 F2 178.63(6) . . ?
F6 P2 F2 88.91(6) . . ?
F1 P2 F2 89.27(5) . . ?
C8 Ni1 C8 95.83(10) . 2 ?
C8 Ni1 N1 166.89(6) . 2 ?
C8 Ni1 N1 82.87(6) 2 2 ?
C8 Ni1 N1 82.87(6) . . ?
C8 Ni1 N1 166.89(6) 2 . ?
N1 Ni1 N1 101.31(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
C1 N1 1.343(2) . ?
C1 C2 1.382(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.352(2) . ?
C5 N2 1.404(2) . ?
C8 N3 1.344(2) . ?
C8 N2 1.361(2) . ?
C8 Ni1 1.8473(15) . ?
C6 C7 1.342(3) . ?
C6 N2 1.388(2) . ?
C6 H7 0.9500 . ?
C7 N3 1.392(2) . ?
C7 H8 0.9500 . ?
C9 N3 1.468(2) . ?
C9 C9 1.518(3) 2 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 Ni1 1.9578(13) . ?
F1 P2 1.6099(10) . ?
F2 P2 1.6198(10) . ?
F3 P2 1.5877(11) . ?
F4 P2 1.5937(10) . ?
F5 P2 1.5988(10) . ?
F6 P2 1.6013(10) . ?
Ni1 C8 1.8473(15) 2 ?
Ni1 N1 1.9578(13) 2 ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C4 2.9(2) . . . . ?
C2 C3 C4 C5 -2.4(2) . . . . ?
C3 C4 C5 N1 -1.3(2) . . . . ?
C3 C4 C5 N2 175.49(14) . . . . ?
N2 C6 C7 N3 0.48(18) . . . . ?
C2 C1 N1 C5 -3.7(2) . . . . ?
C2 C1 N1 Ni1 -178.30(11) . . . . ?
C4 C5 N1 C1 4.3(2) . . . . ?
N2 C5 N1 C1 -172.81(13) . . . . ?
C4 C5 N1 Ni1 179.70(12) . . . . ?
N2 C5 N1 Ni1 2.56(15) . . . . ?
N3 C8 N2 C6 -0.15(16) . . . . ?
Ni1 C8 N2 C6 172.01(10) . . . . ?
N3 C8 N2 C5 176.68(12) . . . . ?
Ni1 C8 N2 C5 -11.16(16) . . . . ?
C7 C6 N2 C8 -0.22(18) . . . . ?
C7 C6 N2 C5 -176.46(15) . . . . ?
N1 C5 N2 C8 5.38(18) . . . . ?
C4 C5 N2 C8 -171.77(14) . . . . ?
N1 C5 N2 C6 -178.56(15) . . . . ?
C4 C5 N2 C6 4.3(3) . . . . ?
N2 C8 N3 C7 0.45(16) . . . . ?
Ni1 C8 N3 C7 -168.15(14) . . . . ?
N2 C8 N3 C9 174.99(13) . . . . ?
Ni1 C8 N3 C9 6.4(3) . . . . ?
C6 C7 N3 C8 -0.61(18) . . . . ?
C6 C7 N3 C9 -175.33(14) . . . . ?
C9 C9 N3 C8 49.6(2) 2 . . . ?
C9 C9 N3 C7 -136.57(15) 2 . . . ?
N3 C8 Ni1 C8 -15.65(14) . . . 2 ?
N2 C8 Ni1 C8 176.38(14) . . . 2 ?
N3 C8 Ni1 N1 67.9(4) . . . 2 ?
N2 C8 Ni1 N1 -100.0(3) . . . 2 ?
N3 C8 Ni1 N1 177.48(19) . . . . ?
N2 C8 Ni1 N1 9.52(10) . . . . ?
C1 N1 Ni1 C8 167.89(14) . . . . ?
C5 N1 Ni1 C8 -6.80(11) . . . . ?
C1 N1 Ni1 C8 82.8(3) . . . 2 ?
C5 N1 Ni1 C8 -91.9(3) . . . 2 ?
C1 N1 Ni1 N1 -24.70(11) . . . 2 ?
C5 N1 Ni1 N1 160.60(12) . . . 2 ?
