#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/55/7005546.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_7005546
loop_
_publ_author_name
'Schaub, Thomas'
'Döring, Christian'
'Radius, Udo'
_publ_section_title
;
 Efficient nickel mediated carbon-carbon bond cleavage of
 organonitriles.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1993
_journal_page_last               2002
_journal_paper_doi               10.1039/b702959d
_journal_year                    2007
_chemical_formula_sum            'C27.5 H37 N6 Ni'
_chemical_formula_weight         510.34
_chemical_name_common            (iPr2Im)2(CN)(2-Pyridyl)Ni(ii)
_chemical_name_systematic
;
(iPr2Im)2(CN)(2-Pyridyl)Ni(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                104.83(3)
_cell_angle_beta                 92.53(3)
_cell_angle_gamma                92.19(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9864(18)
_cell_length_b                   9.6288(19)
_cell_length_c                   16.850(3)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.30
_cell_volume                     1406.2(5)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'STOE IPDS 1'
_diffrn_measurement_method       rotation
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12961
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0652P)²+0.5916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                4238
_reflns_number_total             5081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b702959d.txt
_cod_data_source_block           compound_9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.5916P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.5916P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C27.50 H37 N6 Ni'
_cod_database_code               7005546
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni -0.09621(3) 0.34037(3) 0.242206(16) 0.02172(11) Uani 1 d . . .
N1 N 0.1975(2) 0.4725(2) 0.31192(11) 0.0262(4) Uani 1 d . . .
N2 N 0.1110(2) 0.3317(2) 0.38127(11) 0.0250(4) Uani 1 d . . .
N3 N -0.2837(2) 0.3570(2) 0.09893(11) 0.0279(4) Uani 1 d . . .
N4 N -0.3750(2) 0.1997(2) 0.15608(12) 0.0287(4) Uani 1 d . . .
N5 N -0.2925(3) 0.5341(3) 0.36435(15) 0.0521(7) Uani 1 d . . .
N6 N 0.0782(2) 0.2456(2) 0.10320(12) 0.0285(4) Uani 1 d . . .
H6 H 0.0733 0.3335 0.0989 0.034 Uiso 1 calc R . .
C1 C 0.0788(2) 0.3822(2) 0.31445(12) 0.0236(5) Uani 1 d . . .
C2 C 0.2999(3) 0.4790(3) 0.37663(14) 0.0311(5) Uani 1 d . . .
H2 H 0.3903 0.5346 0.3881 0.037 Uiso 1 calc R . .
C3 C 0.2463(3) 0.3911(3) 0.42004(14) 0.0307(5) Uani 1 d . . .
H3 H 0.2918 0.3734 0.4676 0.037 Uiso 1 calc R . .
C4 C 0.2073(3) 0.5590(3) 0.25149(14) 0.0327(5) Uani 1 d . . .
H4 H 0.1383 0.5130 0.2037 0.039 Uiso 1 calc R . .
C5 C 0.1555(5) 0.7092(4) 0.2890(2) 0.0628(10) Uani 1 d . . .
H5A H 0.0549 0.7022 0.3067 0.094 Uiso 1 calc R . .
H5B H 0.1569 0.7644 0.2483 0.094 Uiso 1 calc R . .
H5C H 0.2218 0.7567 0.3359 0.094 Uiso 1 calc R . .
C6 C 0.3637(4) 0.5618(4) 0.2210(2) 0.0553(8) Uani 1 d . . .
H6A H 0.4330 0.6096 0.2665 0.083 Uiso 1 calc R . .
H6B H 0.3656 0.6136 0.1787 0.083 Uiso 1 calc R . .
H6C H 0.3926 0.4641 0.1985 0.083 Uiso 1 calc R . .
C7 C 0.0170(3) 0.2245(3) 0.40738(14) 0.0304(5) Uani 1 d . . .
H7 H -0.0735 0.2016 0.3699 0.036 Uiso 1 calc R . .
C8 C -0.0321(4) 0.2856(4) 0.49435(18) 0.0534(8) Uani 1 d . . .
H8A H 0.0551 0.3142 0.5319 0.080 Uiso 1 calc R . .
H8B H -0.0920 0.2128 0.5108 0.080 Uiso 1 calc R . .
H8C H -0.0908 0.3686 0.4957 0.080 Uiso 1 calc R . .
C9 C 0.0992(4) 0.0865(3) 0.3993(2) 0.0487(7) Uani 1 d . . .
H9A H 0.1321 0.0536 0.3439 0.073 Uiso 1 calc R . .
H9B H 0.0328 0.0131 0.4109 0.073 Uiso 1 calc R . .
H9C H 0.1851 0.1048 0.4382 0.073 Uiso 1 calc R . .
C10 C -0.2588(2) 0.2967(2) 0.16280(13) 0.0235(5) Uani 1 d . . .
C11 C -0.4146(3) 0.2980(3) 0.05389(16) 0.0393(6) Uani 1 d . . .
H11 H -0.4559 0.3225 0.0074 0.047 Uiso 1 calc R . .
C12 C -0.4704(3) 0.2000(3) 0.08930(16) 0.0395(6) Uani 1 d . . .
H12 H -0.5583 0.1419 0.0721 0.047 Uiso 1 calc R . .
C13 C -0.4011(3) 0.1110(3) 0.21434(16) 0.0343(6) Uani 1 d . . .
H13 H -0.3139 0.1264 0.2542 0.041 Uiso 1 calc R . .
C14 C -0.4138(5) -0.0467(4) 0.1682(2) 0.0655(10) Uani 1 d . . .
H14A H -0.4996 -0.0642 0.1293 0.098 Uiso 1 calc R . .
H14B H -0.4257 -0.1050 0.2069 0.098 Uiso 1 calc R . .
H14C H -0.3241 -0.0718 0.1388 0.098 Uiso 1 calc R . .
C15 C -0.5388(4) 0.1573(4) 0.2618(2) 0.0589(9) Uani 1 d . . .
H15A H -0.5255 0.2580 0.2911 0.088 Uiso 1 calc R . .
H15B H -0.5531 0.0998 0.3007 0.088 Uiso 1 calc R . .
H15C H -0.6255 0.1434 0.2237 0.088 Uiso 1 calc R . .
C16 C -0.1897(3) 0.4762(3) 0.08530(15) 0.0338(6) Uani 1 d . . .
H16 H -0.0853 0.4633 0.1023 0.041 Uiso 1 calc R . .
C17 C -0.2374(4) 0.6190(3) 0.13872(19) 0.0516(8) Uani 1 d . . .
H17A H -0.3381 0.6358 0.1214 0.077 Uiso 1 calc R . .
H17B H -0.1700 0.6964 0.1329 0.077 Uiso 1 calc R . .
H17C H -0.2346 0.6155 0.1958 0.077 Uiso 1 calc R . .
C18 C -0.1956(4) 0.4756(4) -0.00529(18) 0.0521(8) Uani 1 d . . .
H18A H -0.1678 0.3827 -0.0378 0.078 Uiso 1 calc R . .
H18B H -0.1267 0.5502 -0.0133 0.078 Uiso 1 calc R . .
H18C H -0.2959 0.4935 -0.0224 0.078 Uiso 1 calc R . .
C19 C -0.2153(3) 0.4634(3) 0.31951(14) 0.0323(6) Uani 1 d . . .
C20 C 0.0126(2) 0.2057(3) 0.16507(13) 0.0249(5) Uani 1 d . . .
C21 C 0.0230(3) 0.0632(3) 0.17103(15) 0.0340(6) Uani 1 d . . .
H21 H -0.0221 0.0342 0.2139 0.041 Uiso 1 calc R . .
C22 C 0.0994(3) -0.0349(3) 0.11411(17) 0.0397(6) Uani 1 d . . .
H22 H 0.1066 -0.1299 0.1183 0.048 Uiso 1 calc R . .
C23 C 0.1653(3) 0.0089(3) 0.05083(16) 0.0382(6) Uani 1 d . . .
H23 H 0.2174 -0.0552 0.0113 0.046 Uiso 1 calc R . .
C24 C 0.1514(3) 0.1490(3) 0.04819(15) 0.0337(6) Uani 1 d . . .
H24 H 0.1955 0.1794 0.0055 0.040 Uiso 1 calc R . .
C26 C 0.5293(12) 0.8544(8) 0.4656(7) 0.171(5) Uani 1 d . . .
C27 C 0.5999(10) 0.9694(10) 0.4403(5) 0.161(4) Uani 1 d . . .
C25 C 0.4323(10) 0.8830(8) 0.5238(6) 0.178(5) Uani 1 d . . .
C28 C 0.6859(11) 0.9377(13) 0.3905(6) 0.083(3) Uani 0.50 d P . .
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'
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
C10 Ni C1 175.01(9) . . ?
C10 Ni C20 87.02(9) . . ?
C1 Ni C20 88.87(9) . . ?
C10 Ni C19 90.98(10) . . ?
C1 Ni C19 93.30(10) . . ?
C20 Ni C19 175.74(11) . . ?
C1 N1 C2 110.7(2) . . ?
C1 N1 C4 123.6(2) . . ?
C2 N1 C4 125.6(2) . . ?
C1 N2 C3 110.9(2) . . ?
C1 N2 C7 124.58(19) . . ?
C3 N2 C7 124.5(2) . . ?
C10 N3 C11 110.5(2) . . ?
C10 N3 C16 123.5(2) . . ?
C11 N3 C16 125.8(2) . . ?
C10 N4 C12 110.8(2) . . ?
C10 N4 C13 124.8(2) . . ?
C12 N4 C13 124.3(2) . . ?
C24 N6 C20 119.8(2) . . ?
C24 N6 H6 120.1 . . ?
C20 N6 H6 120.1 . . ?
N1 C1 N2 104.44(19) . . ?
N1 C1 Ni 127.66(17) . . ?
N2 C1 Ni 127.88(18) . . ?
C3 C2 N1 107.3(2) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C2 C3 N2 106.7(2) . . ?
C2 C3 H3 126.7 . . ?
N2 C3 H3 126.7 . . ?
N1 C4 C6 111.1(2) . . ?
N1 C4 C5 109.5(2) . . ?
C6 C4 C5 112.4(3) . . ?
N1 C4 H4 107.9 . . ?
C6 C4 H4 107.9 . . ?
C5 C4 H4 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C9 110.0(2) . . ?
N2 C7 C8 110.8(2) . . ?
C9 C7 C8 112.2(2) . . ?
N2 C7 H7 107.9 . . ?
C9 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 N3 104.5(2) . . ?
N4 C10 Ni 128.52(18) . . ?
N3 C10 Ni 126.97(18) . . ?
C12 C11 N3 106.9(2) . . ?
C12 C11 H11 126.6 . . ?
N3 C11 H11 126.6 . . ?
C11 C12 N4 107.3(2) . . ?
C11 C12 H12 126.4 . . ?
N4 C12 H12 126.4 . . ?
N4 C13 C14 109.6(2) . . ?
N4 C13 C15 110.4(2) . . ?
C14 C13 C15 112.1(3) . . ?
N4 C13 H13 108.2 . . ?
C14 C13 H13 108.2 . . ?
C15 C13 H13 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C18 111.1(2) . . ?
N3 C16 C17 109.8(2) . . ?
C18 C16 C17 111.3(2) . . ?
N3 C16 H16 108.2 . . ?
C18 C16 H16 108.2 . . ?
C17 C16 H16 108.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N5 C19 Ni 177.0(2) . . ?
N6 C20 C21 119.0(2) . . ?
N6 C20 Ni 120.38(18) . . ?
C21 C20 Ni 120.61(18) . . ?
C22 C21 C20 120.5(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.3(3) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 117.6(2) . . ?
C24 C23 H23 121.2 . . ?
C22 C23 H23 121.2 . . ?
N6 C24 C23 123.8(2) . . ?
N6 C24 H24 118.1 . . ?
C23 C24 H24 118.1 . . ?
C25 C26 C27 119.5(7) . . ?
C28 C27 C26 116.2(11) . . ?
C28 C27 C25 122.2(15) . 2_676 ?
C26 C27 C25 121.6(11) . 2_676 ?
C26 C25 C27 118.9(11) . 2_676 ?
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
Ni C10 1.896(2) . ?
Ni C1 1.911(2) . ?
Ni C20 1.916(2) . ?
Ni C19 1.917(3) . ?
N1 C1 1.359(3) . ?
N1 C2 1.383(3) . ?
N1 C4 1.474(3) . ?
N2 C1 1.360(3) . ?
N2 C3 1.385(3) . ?
N2 C7 1.473(3) . ?
N3 C10 1.361(3) . ?
N3 C11 1.390(3) . ?
N3 C16 1.471(3) . ?
N4 C10 1.355(3) . ?
N4 C12 1.385(3) . ?
N4 C13 1.478(3) . ?
N5 C19 1.156(3) . ?
N6 C24 1.348(3) . ?
N6 C20 1.351(3) . ?
N6 H6 0.8700 . ?
C2 C3 1.341(4) . ?
C2 H2 0.9400 . ?
C3 H3 0.9400 . ?
C4 C6 1.519(4) . ?
C4 C5 1.523(4) . ?
C4 H4 0.9900 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 C9 1.524(4) . ?
C7 C8 1.525(4) . ?
C7 H7 0.9900 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C11 C12 1.333(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.516(4) . ?
C13 C15 1.521(4) . ?
C13 H13 0.9900 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 C18 1.523(4) . ?
C16 C17 1.526(4) . ?
C16 H16 0.9900 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C20 C21 1.408(4) . ?
C21 C22 1.388(4) . ?
C21 H21 0.9400 . ?
C22 C23 1.390(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.372(4) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C26 C25 1.324(17) . ?
C26 C27 1.422(15) . ?
C27 C28 1.157(12) . ?
C27 C25 1.441(8) 2_676 ?
C25 C27 1.441(8) 2_676 ?
