#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:17:47 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179718 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/20/7002080.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_7002080
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            'C30 H46 N4 Ni S'
_chemical_formula_weight         553.48
_chemical_name_common            (iPr2Im)2(SMe)(pTolyl)Ni(ii)
_chemical_name_systematic
;
(iPr2Im)2(SMe)(pTolyl)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                95.19(3)
_cell_angle_beta                 99.35(3)
_cell_angle_gamma                107.21(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9551(18)
_cell_length_b                   9.5880(19)
_cell_length_c                   19.095(4)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      2.40
_cell_volume                     1528.5(6)
_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 0.917
_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  0.0767
_diffrn_reflns_av_sigmaI/netI    0.0856
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11091
_diffrn_reflns_theta_full        25.89
_diffrn_reflns_theta_max         25.89
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  0.8922
_exptl_absorpt_correction_T_min  0.7633
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.068
_refine_ls_shift/su_mean         0.043
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0529P)²+4.8569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1800
_refine_ls_wR_factor_ref         0.1942
_reflns_number_gt                3909
_reflns_number_total             5449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b907124p.txt
_cod_data_source_block           compound2
_cod_original_cell_volume        1528.6(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7002080
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 0.7781(2) 1.08954(16) 0.77724(10) 0.0481(5) Uani 1 1 d . . .
Ni1 Ni 0.55236(9) 0.90265(7) 0.73591(4) 0.0262(2) Uani 1 1 d . . .
N1 N 0.7654(6) 0.7354(5) 0.7053(2) 0.0320(11) Uani 1 1 d . . .
N2 N 0.7139(6) 0.7188(5) 0.8099(2) 0.0326(11) Uani 1 1 d . . .
N3 N 0.3935(6) 1.1047(5) 0.6750(2) 0.0340(11) Uani 1 1 d . . .
N4 N 0.3474(6) 1.0648(5) 0.7783(2) 0.0364(11) Uani 1 1 d . . .
C1 C 0.6809(6) 0.7784(5) 0.7501(3) 0.0293(12) Uani 1 1 d . . .
C2 C 0.8503(8) 0.6499(6) 0.7370(3) 0.0451(16) Uani 1 1 d . . .
H2A H 0.9173 0.6067 0.7162 0.054 Uiso 1 1 calc R . .
C3 C 0.8188(8) 0.6408(6) 0.8020(3) 0.0440(16) Uani 1 1 d . . .
H3A H 0.8601 0.5906 0.8364 0.053 Uiso 1 1 calc R . .
C4 C 0.6550(8) 0.7425(6) 0.8759(3) 0.0433(15) Uani 1 1 d . . .
H4A H 0.5696 0.7876 0.8642 0.052 Uiso 1 1 calc R . .
C5 C 0.7868(9) 0.8520(8) 0.9324(3) 0.059(2) Uani 1 1 d . . .
H5A H 0.8274 0.9431 0.9133 0.088 Uiso 1 1 calc R . .
H5B H 0.8725 0.8108 0.9453 0.088 Uiso 1 1 calc R . .
H5C H 0.7448 0.8719 0.9746 0.088 Uiso 1 1 calc R . .
C6 C 0.5807(10) 0.5966(8) 0.9012(4) 0.066(2) Uani 1 1 d . . .
H6A H 0.4964 0.5327 0.8631 0.099 Uiso 1 1 calc R . .
H6B H 0.5366 0.6144 0.9430 0.099 Uiso 1 1 calc R . .
H6C H 0.6617 0.5497 0.9135 0.099 Uiso 1 1 calc R . .
C7 C 0.7745(8) 0.7793(6) 0.6341(3) 0.0404(14) Uani 1 1 d . . .
H7A H 0.7019 0.8389 0.6247 0.048 Uiso 1 1 calc R . .
C8 C 0.7136(11) 0.6429(8) 0.5771(4) 0.065(2) Uani 1 1 d . . .
H8A H 0.6063 0.5862 0.5805 0.097 Uiso 1 1 calc R . .
H8B H 0.7831 0.5826 0.5845 0.097 Uiso 1 1 calc R . .
H8C H 0.7127 0.6729 0.5299 0.097 Uiso 1 1 calc R . .
C9 C 0.9414(9) 0.8770(10) 0.6338(5) 0.071(2) Uani 1 1 d . . .
H9A H 0.9712 0.9615 0.6711 0.107 Uiso 1 1 calc R . .
H9B H 0.9446 0.9106 0.5875 0.107 Uiso 1 1 calc R . .
H9C H 1.0155 0.8215 0.6426 0.107 Uiso 1 1 calc R . .
C10 C 0.4220(7) 1.0250(5) 0.7272(3) 0.0308(12) Uani 1 1 d . . .
C11 C 0.3071(8) 1.1949(7) 0.6937(4) 0.0461(16) Uani 1 1 d . . .
H11A H 0.2751 1.2612 0.6661 0.055 Uiso 1 1 calc R . .
C12 C 0.2776(8) 1.1704(7) 0.7582(4) 0.0479(17) Uani 1 1 d . . .
H12A H 0.2208 1.2157 0.7849 0.058 Uiso 1 1 calc R . .
C13 C 0.3460(9) 1.0080(7) 0.8477(3) 0.0443(16) Uani 1 1 d . . .
H13A H 0.3791 0.9184 0.8435 0.053 Uiso 1 1 calc R . .
C14 C 0.4683(10) 1.1199(10) 0.9063(4) 0.076(3) Uani 1 1 d . . .
H14A H 0.5721 1.1438 0.8931 0.114 Uiso 1 1 calc R . .
H14B H 0.4731 1.0788 0.9509 0.114 Uiso 1 1 calc R . .
H14C H 0.4381 1.2087 0.9125 0.114 Uiso 1 1 calc R . .
C15 C 0.1829(11) 0.9636(10) 0.8642(4) 0.074(2) Uani 1 1 d . . .
H15A H 0.1100 0.8913 0.8253 0.112 Uiso 1 1 calc R . .
H15B H 0.1476 1.0497 0.8697 0.112 Uiso 1 1 calc R . .
H15C H 0.1851 0.9211 0.9084 0.112 Uiso 1 1 calc R . .
C16 C 0.4448(8) 1.0954(7) 0.6055(3) 0.0419(15) Uani 1 1 d . . .
H16A H 0.5187 1.0361 0.6080 0.050 Uiso 1 1 calc R . .
C17 C 0.5332(10) 1.2484(8) 0.5909(4) 0.067(2) Uani 1 1 d . . .
H17A H 0.6244 1.2950 0.6296 0.100 Uiso 1 1 calc R . .
H17B H 0.4622 1.3078 0.5878 0.100 Uiso 1 1 calc R . .
H17C H 0.5695 1.2398 0.5460 0.100 Uiso 1 1 calc R . .
C18 C 0.3015(9) 1.0179(8) 0.5455(4) 0.0550(18) Uani 1 1 d . . .
H18A H 0.2485 0.9201 0.5556 0.082 Uiso 1 1 calc R . .
H18B H 0.3369 1.0097 0.5004 0.082 Uiso 1 1 calc R . .
H18C H 0.2277 1.0746 0.5423 0.082 Uiso 1 1 calc R . .
C19 C 0.7540(8) 1.2704(6) 0.7811(4) 0.0481(17) Uani 1 1 d . . .
H19A H 0.8566 1.3450 0.7995 0.072 Uiso 1 1 calc R . .
H19B H 0.6809 1.2778 0.8125 0.072 Uiso 1 1 calc R . .
H19C H 0.7115 1.2854 0.7333 0.072 Uiso 1 1 calc R . .
C20 C 0.3729(7) 0.7279(6) 0.6964(3) 0.0327(13) Uani 1 1 d . . .
C21 C 0.2834(7) 0.6317(6) 0.7360(3) 0.0341(13) Uani 1 1 d . . .
H21A H 0.3075 0.6551 0.7863 0.041 Uiso 1 1 calc R . .
C22 C 0.1591(7) 0.5017(6) 0.7047(4) 0.0413(15) Uani 1 1 d . . .
H22A H 0.1031 0.4426 0.7347 0.050 Uiso 1 1 calc R . .
C23 C 0.1166(7) 0.4581(6) 0.6317(4) 0.0418(16) Uani 1 1 d . . .
C24 C 0.2049(8) 0.5519(6) 0.5910(3) 0.0428(15) Uani 1 1 d . . .
H24A H 0.1811 0.5283 0.5407 0.051 Uiso 1 1 calc R . .
C25 C 0.3283(7) 0.6808(6) 0.6234(3) 0.0384(14) Uani 1 1 d . . .
H25A H 0.3848 0.7392 0.5934 0.046 Uiso 1 1 calc R . .
C26 C -0.0169(8) 0.3176(7) 0.5974(4) 0.063(2) Uani 1 1 d . . .
H26A H -0.0626 0.2674 0.6345 0.095 Uiso 1 1 calc R . .
H26B H 0.0253 0.2534 0.5699 0.095 Uiso 1 1 calc R . .
H26C H -0.0988 0.3421 0.5658 0.095 Uiso 1 1 calc R . .
C32 C 0.0772(15) 0.6340(17) 0.0175(8) 0.103(4) Uani 1 1 d . . .
C30 C -0.1284(16) 0.556(2) 0.0795(7) 0.144(6) Uani 1 1 d . . .
H30A H -0.2116 0.6031 0.0695 0.172 Uiso 1 1 calc R . .
H30B H -0.0906 0.5614 0.1311 0.172 Uiso 1 1 calc R . .
C31 C -0.026(2) 0.588(3) 0.0454(8) 0.173(10) Uani 1 1 d . . .
H31A H -0.0989 0.6140 0.0078 0.208 Uiso 1 1 calc R . .
C33 C 0.169(2) 0.616(2) -0.0290(12) 0.190(10) Uani 1 1 d . . .
H33A H 0.2433 0.5926 0.0089 0.228 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 114.5(2) . . ?
C10 Ni1 C1 176.6(2) . . ?
C10 Ni1 C20 91.8(2) . . ?
C1 Ni1 C20 88.2(2) . . ?
C10 Ni1 S1 94.42(17) . . ?
C1 Ni1 S1 85.75(16) . . ?
C20 Ni1 S1 173.16(16) . . ?
C1 N1 C2 110.8(5) . . ?
C1 N1 C7 124.9(4) . . ?
C2 N1 C7 124.2(5) . . ?
C1 N2 C3 110.7(5) . . ?
C1 N2 C4 124.5(5) . . ?
C3 N2 C4 124.7(5) . . ?
C10 N3 C11 111.6(5) . . ?
C10 N3 C16 124.7(5) . . ?
C11 N3 C16 123.7(5) . . ?
C10 N4 C12 111.1(5) . . ?
C10 N4 C13 124.6(5) . . ?
C12 N4 C13 124.2(5) . . ?
N1 C1 N2 104.5(4) . . ?
N1 C1 Ni1 128.4(4) . . ?
N2 C1 Ni1 127.0(4) . . ?
C3 C2 N1 106.8(6) . . ?
C2 C3 N2 107.2(5) . . ?
N2 C4 C5 110.2(5) . . ?
N2 C4 C6 110.9(5) . . ?
C5 C4 C6 113.6(6) . . ?
N1 C7 C9 110.0(5) . . ?
N1 C7 C8 109.9(5) . . ?
C9 C7 C8 114.3(6) . . ?
N3 C10 N4 103.8(4) . . ?
N3 C10 Ni1 130.1(4) . . ?
N4 C10 Ni1 125.8(4) . . ?
C12 C11 N3 107.0(5) . . ?
C11 C12 N4 106.5(5) . . ?
N4 C13 C15 111.7(6) . . ?
N4 C13 C14 109.8(5) . . ?
C15 C13 C14 113.0(6) . . ?
N3 C16 C17 110.6(5) . . ?
N3 C16 C18 110.2(5) . . ?
C17 C16 C18 111.1(5) . . ?
C25 C20 C21 112.9(5) . . ?
C25 C20 Ni1 121.2(5) . . ?
C21 C20 Ni1 125.7(4) . . ?
C20 C21 C22 123.5(5) . . ?
C23 C22 C21 122.2(6) . . ?
C22 C23 C24 115.4(5) . . ?
C22 C23 C26 122.6(7) . . ?
C24 C23 C26 122.0(6) . . ?
C23 C24 C25 121.4(6) . . ?
C20 C25 C24 124.6(6) . . ?
C31 C32 C33 151(2) . . ?
C31 C30 C33 81.5(18) . 2_565 ?
C32 C31 C30 172(3) . . ?
C32 C31 C33 126(2) . 2_565 ?
C30 C31 C33 61.4(16) . 2_565 ?
C32 C33 C30 120.0(17) . 2_565 ?
C32 C33 C31 82.9(15) . 2_565 ?
C30 C33 C31 37.1(7) 2_565 2_565 ?
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 1.806(6) . ?
S1 Ni1 2.2370(19) . ?
Ni1 C10 1.885(5) . ?
Ni1 C1 1.893(5) . ?
Ni1 C20 1.934(6) . ?
N1 C1 1.344(7) . ?
N1 C2 1.388(7) . ?
N1 C7 1.467(7) . ?
N2 C1 1.351(7) . ?
N2 C3 1.381(7) . ?
N2 C4 1.467(8) . ?
N3 C10 1.345(7) . ?
N3 C11 1.381(7) . ?
N3 C16 1.476(8) . ?
N4 C10 1.356(7) . ?
N4 C12 1.390(7) . ?
N4 C13 1.478(7) . ?
C2 C3 1.322(9) . ?
C4 C5 1.519(9) . ?
C4 C6 1.519(9) . ?
C7 C9 1.512(10) . ?
C7 C8 1.524(8) . ?
C11 C12 1.326(9) . ?
C13 C15 1.489(11) . ?
C13 C14 1.514(10) . ?
C16 C17 1.522(9) . ?
C16 C18 1.522(9) . ?
C20 C25 1.380(8) . ?
C20 C21 1.398(8) . ?
C21 C22 1.406(8) . ?
C22 C23 1.376(9) . ?
C23 C24 1.394(9) . ?
C23 C26 1.519(8) . ?
C24 C25 1.402(8) . ?
C32 C31 1.134(16) . ?
C32 C33 1.33(3) . ?
C30 C31 1.195(19) . ?
C30 C33 1.74(2) 2_565 ?
C31 C33 1.96(3) 2_565 ?
C33 C30 1.74(2) 2_565 ?
C33 C31 1.96(3) 2_565 ?
