#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:17:47 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179718 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/20/7002083.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_7002083
loop_
_publ_author_name
'Schaub, Thomas'
'Backes, Marc'
'Plietzsch, Oliver'
'Radius, Udo'
_publ_section_title
;
 Facile C--S, S--H, and S--S bond cleavage using a nickel(0) NHC
 complex
;
_journal_issue                   35
_journal_name_full               'Dalton Transactions'
_journal_page_first              7071
_journal_paper_doi               10.1039/b907124p
_journal_year                    2009
_chemical_formula_sum            'C22 H42 N4 Ni S'
_chemical_formula_weight         453.37
_chemical_name_common            (iPr2Im)2(H)(StBu)Ni(ii)
_chemical_name_systematic
;
(iPr2Im)2(H)(StBu)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
_cell_angle_alpha                95.40(3)
_cell_angle_beta                 91.24(3)
_cell_angle_gamma                109.25(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7691(18)
_cell_length_b                   9.2488(18)
_cell_length_c                   17.285(4)
_cell_measurement_reflns_used    5688
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.4
_cell_volume                     1315.6(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_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.917
_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  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8073
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0431
_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)+(0.0633P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                3420
_reflns_number_total             4755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b907124p.txt
_cod_data_source_block           compound8
_cod_original_cell_volume        1315.5(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7002083
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.43071(10) 1.06634(9) 0.77578(7) 0.0434(3) Uani 1 1 d . . .
Ni1 Ni 0.53653(4) 0.88117(4) 0.74649(3) 0.02269(13) Uani 1 1 d . . .
H1 H 0.594(5) 0.755(5) 0.729(3) 0.057(12) Uiso 1 1 d . . .
N1 N 0.8875(3) 1.0105(3) 0.75919(17) 0.0285(6) Uani 1 1 d . . .
N2 N 0.7966(3) 0.9996(3) 0.64198(17) 0.0313(6) Uani 1 1 d . . .
N3 N 0.2224(3) 0.6345(3) 0.72904(17) 0.0305(6) Uani 1 1 d . . .
N4 N 0.3076(3) 0.6952(3) 0.84794(18) 0.0311(6) Uani 1 1 d . . .
C1 C 0.7474(3) 0.9740(3) 0.7151(2) 0.0255(7) Uani 1 1 d . . .
C2 C 1.0210(4) 1.0538(4) 0.7138(2) 0.0378(9) Uani 1 1 d . . .
H2A H 1.1302 1.0819 0.7312 0.045 Uiso 1 1 calc R . .
C3 C 0.9645(4) 1.0478(4) 0.6408(2) 0.0423(9) Uani 1 1 d . . .
H3A H 1.0262 1.0715 0.5971 0.051 Uiso 1 1 calc R . .
C4 C 0.6860(4) 0.9548(5) 0.5734(2) 0.0426(9) Uani 1 1 d . . .
H4A H 0.5775 0.9507 0.5901 0.051 Uiso 1 1 calc R . .
C5 C 0.7355(6) 1.0707(6) 0.5149(3) 0.0611(12) Uani 1 1 d . . .
H5A H 0.7404 1.1712 0.5391 0.092 Uiso 1 1 calc R . .
H5B H 0.6568 1.0398 0.4710 0.092 Uiso 1 1 calc R . .
H5C H 0.8410 1.0757 0.4971 0.092 Uiso 1 1 calc R . .
C6 C 0.6742(6) 0.7938(6) 0.5375(3) 0.0662(14) Uani 1 1 d . . .
H6A H 0.6415 0.7218 0.5763 0.099 Uiso 1 1 calc R . .
H6B H 0.7787 0.7954 0.5195 0.099 Uiso 1 1 calc R . .
H6C H 0.5947 0.7618 0.4938 0.099 Uiso 1 1 calc R . .
C7 C 0.8931(4) 0.9863(4) 0.8413(2) 0.0356(8) Uani 1 1 d . . .
H7A H 0.7876 0.9820 0.8622 0.043 Uiso 1 1 calc R . .
C8 C 0.9159(6) 0.8303(5) 0.8484(3) 0.0646(14) Uani 1 1 d . . .
H8A H 0.8298 0.7494 0.8181 0.097 Uiso 1 1 calc R . .
H8B H 0.9129 0.8105 0.9026 0.097 Uiso 1 1 calc R . .
H8C H 1.0195 0.8324 0.8290 0.097 Uiso 1 1 calc R . .
C9 C 1.0240(5) 1.1188(5) 0.8876(3) 0.0473(10) Uani 1 1 d . . .
H9A H 1.0038 1.2144 0.8822 0.071 Uiso 1 1 calc R . .
H9B H 1.1287 1.1252 0.8682 0.071 Uiso 1 1 calc R . .
H9C H 1.0232 1.1013 0.9421 0.071 Uiso 1 1 calc R . .
C10 C 0.3459(4) 0.7342(3) 0.7760(2) 0.0259(7) Uani 1 1 d . . .
C11 C 0.1124(4) 0.5335(4) 0.7722(2) 0.0385(9) Uani 1 1 d . . .
H11A H 0.0184 0.4531 0.7527 0.046 Uiso 1 1 calc R . .
C12 C 0.1649(4) 0.5717(4) 0.8459(2) 0.0395(9) Uani 1 1 d . . .
H12A H 0.1149 0.5243 0.8888 0.047 Uiso 1 1 calc R . .
C13 C 0.4042(4) 0.7770(4) 0.9186(2) 0.0369(8) Uani 1 1 d . . .
H13A H 0.4933 0.8653 0.9030 0.044 Uiso 1 1 calc R . .
C14 C 0.4803(6) 0.6734(6) 0.9572(3) 0.0648(13) Uani 1 1 d . . .
H14A H 0.5438 0.6360 0.9201 0.097 Uiso 1 1 calc R . .
H14B H 0.3956 0.5867 0.9741 0.097 Uiso 1 1 calc R . .
H14C H 0.5497 0.7316 1.0018 0.097 Uiso 1 1 calc R . .
C15 C 0.3033(5) 0.8417(5) 0.9741(3) 0.0522(11) Uani 1 1 d . . .
H15A H 0.2588 0.9078 0.9474 0.078 Uiso 1 1 calc R . .
H15B H 0.3713 0.9008 1.0189 0.078 Uiso 1 1 calc R . .
H15C H 0.2158 0.7574 0.9911 0.078 Uiso 1 1 calc R . .
C16 C 0.2109(4) 0.6351(4) 0.6445(2) 0.0423(9) Uani 1 1 d . . .
H16A H 0.2940 0.7305 0.6316 0.051 Uiso 1 1 calc R . .
C17 C 0.2507(7) 0.4999(6) 0.6039(3) 0.0756(16) Uani 1 1 d . . .
H17A H 0.3566 0.5028 0.6230 0.113 Uiso 1 1 calc R . .
H17B H 0.2508 0.5065 0.5482 0.113 Uiso 1 1 calc R . .
H17C H 0.1701 0.4043 0.6146 0.113 Uiso 1 1 calc R . .
C18 C 0.0461(6) 0.6422(6) 0.6183(3) 0.0670(14) Uani 1 1 d . . .
H18A H 0.0287 0.7309 0.6463 0.101 Uiso 1 1 calc R . .
H18B H -0.0383 0.5490 0.6290 0.101 Uiso 1 1 calc R . .
H18C H 0.0434 0.6513 0.5629 0.101 Uiso 1 1 calc R . .
C19 C 0.5511(4) 1.2685(4) 0.7655(2) 0.0319(8) Uani 1 1 d . . .
C20 C 0.6055(7) 1.2919(5) 0.6849(3) 0.0708(15) Uani 1 1 d . . .
H20A H 0.6679 1.3995 0.6827 0.106 Uiso 1 1 calc R . .
H20B H 0.5117 1.2625 0.6486 0.106 Uiso 1 1 calc R . .
H20C H 0.6720 1.2289 0.6711 0.106 Uiso 1 1 calc R . .
C21 C 0.6978(5) 1.3211(5) 0.8209(3) 0.0561(12) Uani 1 1 d . . .
H21A H 0.7603 1.4272 0.8148 0.084 Uiso 1 1 calc R . .
H21B H 0.7637 1.2564 0.8098 0.084 Uiso 1 1 calc R . .
H21C H 0.6641 1.3138 0.8739 0.084 Uiso 1 1 calc R . .
C22 C 0.4434(5) 1.3645(4) 0.7892(3) 0.0556(12) Uani 1 1 d . . .
H22A H 0.5014 1.4722 0.7846 0.083 Uiso 1 1 calc R . .
H22B H 0.4150 1.3518 0.8427 0.083 Uiso 1 1 calc R . .
H22C H 0.3457 1.3301 0.7554 0.083 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C19 S1 Ni1 119.63(12) . . ?
C1 Ni1 C10 162.23(12) . . ?
C1 Ni1 S1 107.89(10) . . ?
C10 Ni1 S1 89.74(10) . . ?
C1 Ni1 H1 75.8(16) . . ?
C10 Ni1 H1 86.6(17) . . ?
S1 Ni1 H1 176.3(17) . . ?
C1 N1 C2 111.1(3) . . ?
C1 N1 C7 123.2(3) . . ?
C2 N1 C7 125.2(3) . . ?
C1 N2 C3 111.1(3) . . ?
C1 N2 C4 123.0(3) . . ?
C3 N2 C4 125.0(3) . . ?
C10 N3 C11 110.7(3) . . ?
C10 N3 C16 123.6(3) . . ?
C11 N3 C16 125.7(3) . . ?
C10 N4 C12 111.4(3) . . ?
C10 N4 C13 123.4(3) . . ?
C12 N4 C13 125.2(3) . . ?
N1 C1 N2 104.0(3) . . ?
N1 C1 Ni1 126.9(3) . . ?
N2 C1 Ni1 128.5(2) . . ?
C3 C2 N1 107.0(3) . . ?
C3 C2 H2A 126.5 . . ?
N1 C2 H2A 126.5 . . ?
C2 C3 N2 106.8(3) . . ?
C2 C3 H3A 126.6 . . ?
N2 C3 H3A 126.6 . . ?
N2 C4 C5 111.6(3) . . ?
N2 C4 C6 109.9(3) . . ?
C5 C4 C6 111.4(4) . . ?
N2 C4 H4A 107.9 . . ?
C5 C4 H4A 107.9 . . ?
C6 C4 H4A 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 . . ?
N1 C7 C9 111.1(3) . . ?
N1 C7 C8 109.0(3) . . ?
C9 C7 C8 112.3(3) . . ?
N1 C7 H7A 108.1 . . ?
C9 C7 H7A 108.1 . . ?
C8 C7 H7A 108.1 . . ?
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 103.9(3) . . ?
N4 C10 Ni1 127.9(2) . . ?
N3 C10 Ni1 128.0(3) . . ?
C12 C11 N3 107.0(3) . . ?
C12 C11 H11A 126.5 . . ?
N3 C11 H11A 126.5 . . ?
C11 C12 N4 106.9(3) . . ?
C11 C12 H12A 126.5 . . ?
N4 C12 H12A 126.5 . . ?
N4 C13 C14 110.7(3) . . ?
N4 C13 C15 110.8(3) . . ?
C14 C13 C15 112.4(4) . . ?
N4 C13 H13A 107.6 . . ?
C14 C13 H13A 107.6 . . ?
C15 C13 H13A 107.6 . . ?
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 C17 110.5(4) . . ?
N3 C16 C18 110.3(4) . . ?
C17 C16 C18 113.8(4) . . ?
N3 C16 H16A 107.3 . . ?
C17 C16 H16A 107.3 . . ?
C18 C16 H16A 107.3 . . ?
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 . . ?
C20 C19 C21 108.5(4) . . ?
C20 C19 C22 111.1(4) . . ?
C21 C19 C22 107.9(3) . . ?
C20 C19 S1 112.8(3) . . ?
C21 C19 S1 110.2(3) . . ?
C22 C19 S1 106.3(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
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
S1 C19 1.847(3) . ?
S1 Ni1 2.2260(11) . ?
Ni1 C1 1.880(3) . ?
Ni1 C10 1.890(3) . ?
Ni1 H1 1.43(4) . ?
N1 C1 1.358(4) . ?
N1 C2 1.392(4) . ?
N1 C7 1.460(5) . ?
N2 C1 1.360(5) . ?
N2 C3 1.391(4) . ?
N2 C4 1.453(5) . ?
N3 C10 1.358(4) . ?
N3 C11 1.389(4) . ?
N3 C16 1.462(5) . ?
N4 C10 1.347(5) . ?
N4 C12 1.385(4) . ?
N4 C13 1.463(5) . ?
C2 C3 1.334(6) . ?
C2 H2A 0.9400 . ?
C3 H3A 0.9400 . ?
C4 C5 1.508(6) . ?
C4 C6 1.528(6) . ?
C4 H4A 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 1.519(5) . ?
C7 C8 1.536(6) . ?
C7 H7A 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 1.319(6) . ?
C11 H11A 0.9400 . ?
C12 H12A 0.9400 . ?
C13 C14 1.526(6) . ?
C13 C15 1.529(5) . ?
C13 H13A 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 C17 1.520(6) . ?
C16 C18 1.529(6) . ?
C16 H16A 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 . ?
C19 C20 1.494(6) . ?
C19 C21 1.502(5) . ?
C19 C22 1.532(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
