#------------------------------------------------------------------------------
#$Date: 2014-03-15 13:45:36 +0200 (Sat, 15 Mar 2014) $
#$Revision: 106525 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/18/7101897.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_7101897
loop_
_publ_author_name
'Schaub, Thomas'
'Backes, Marc'
'Radius, Udo'
_publ_section_title
;
 Unusual nickel-mediated C-S cleavage of alkyl and aryl sulfoxides.
;
_journal_issue                   20
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2037
_journal_page_last               2039
_journal_year                    2007
_chemical_formula_sum            'C30 H42 N4 Ni O S'
_chemical_formula_weight         565.45
_chemical_name_common
;Bis-(1,3-di(isopropyl)imidazol-2-ylidene-
)(Phenylthiooxyl)(phenyl)nickel(ii)
;
_chemical_name_systematic
;
Bis-{1,3-di(isopropyl)imidazol-2-ylidene-}(Phenylthiooxyl)(phenyl)nickel(II)
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.861(2)
_cell_length_b                   19.288(4)
_cell_length_c                   28.695(6)
_cell_measurement_reflns_used    6910
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.3
_cell_volume                     6011(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE STADI4-CCD'
_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  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27925
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         3.90
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.8922
_exptl_absorpt_correction_T_min  0.6633
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.162
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.255
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0645
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.1166P)^2^+0.4949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.2007
_reflns_number_gt                3813
_reflns_number_total             4295
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    b618632g.txt
_[local]_cod_data_source_block   compound4
_[local]_cod_cif_authors_sg_H-M  Pbca
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'
O O 0.0106 0.0060 '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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O O 1.0003(3) 0.4289(2) 0.13514(11) 0.0615(10) Uani 1 d .
S S 1.12287(12) 0.41516(7) 0.10606(5) 0.0516(4) Uani 1 d .
Ni Ni 0.86293(5) 0.36560(3) 0.128771(18) 0.0346(3) Uani 1 d .
C1 C 0.8515(4) 0.3705(2) 0.19485(16) 0.0363(11) Uani 1 d .
C2 C 0.8264(5) 0.4118(2) 0.26793(15) 0.0481(12) Uani 1 d .
H2 H 0.8023 0.4407 0.2927 0.058 Uiso 1 calc R
C3 C 0.8900(4) 0.3536(2) 0.27108(16) 0.0438(12) Uani 1 d .
H3 H 0.9198 0.3332 0.2986 0.053 Uiso 1 calc R
C4 C 0.9753(4) 0.2659(2) 0.21290(17) 0.0419(11) Uani 1 d .
H4 H 0.9608 0.2571 0.1794 0.050 Uiso 1 calc R
C5 C 1.1105(5) 0.2794(3) 0.2194(3) 0.0764(19) Uani 1 d .
H5A H 1.1344 0.3195 0.2011 0.115 Uiso 1 calc R
H5B H 1.1570 0.2393 0.2091 0.115 Uiso 1 calc R
H5C H 1.1273 0.2881 0.2521 0.115 Uiso 1 calc R
C6 C 0.9300(6) 0.2034(2) 0.23965(19) 0.0652(15) Uani 1 d .
H6A H 0.9431 0.2107 0.2727 0.098 Uiso 1 calc R
H6B H 0.9749 0.1626 0.2296 0.098 Uiso 1 calc R
H6C H 0.8428 0.1968 0.2337 0.098 Uiso 1 calc R
C7 C 0.7361(6) 0.4811(3) 0.20218(18) 0.0668(17) Uani 1 d .
H7 H 0.7163 0.4709 0.1692 0.080 Uiso 1 calc R
C8 C 0.8161(7) 0.5449(3) 0.2035(4) 0.168(6) Uani 1 d .
H8A H 0.8244 0.5606 0.2354 0.253 Uiso 1 calc R
H8B H 0.7786 0.5811 0.1849 0.253 Uiso 1 calc R
H8C H 0.8967 0.5339 0.1910 0.253 Uiso 1 calc R
C9 C 0.6186(5) 0.4942(3) 0.2274(3) 0.083(2) Uani 1 d .
H9A H 0.5709 0.4517 0.2287 0.125 Uiso 1 calc R
H9B H 0.5720 0.5296 0.2111 0.125 Uiso 1 calc R
H9C H 0.6364 0.5098 0.2588 0.125 Uiso 1 calc R
C10 C 0.8745(4) 0.36061(19) 0.06221(15) 0.0310(10) Uani 1 d .
C11 C 0.9191(4) 0.3314(2) -0.01120(15) 0.0409(11) Uani 1 d .
H11 H 0.9496 0.3065 -0.0369 0.049 Uiso 1 calc R
C12 C 0.8589(4) 0.3910(2) -0.01291(15) 0.0398(11) Uani 1 d .
H12 H 0.8391 0.4164 -0.0398 0.048 Uiso 1 calc R
C13 C 0.7696(4) 0.47245(19) 0.04690(15) 0.0376(10) Uani 1 d .
H13 H 0.7522 0.4687 0.0807 0.045 Uiso 1 calc R
C14 C 0.6493(5) 0.4802(3) 0.02208(19) 0.0577(14) Uani 1 d .
H14A H 0.6642 0.4894 -0.0107 0.087 Uiso 1 calc R
H14B H 0.6036 0.5185 0.0356 0.087 Uiso 1 calc R
H14C H 0.6020 0.4378 0.0252 0.087 Uiso 1 calc R
C15 C 0.8536(5) 0.5334(2) 0.0398(2) 0.0589(15) Uani 1 d .
H15A H 0.9301 0.5257 0.0564 0.088 Uiso 1 calc R
H15B H 0.8143 0.5751 0.0515 0.088 Uiso 1 calc R
H15C H 0.8707 0.5388 0.0068 0.088 Uiso 1 calc R
C16 C 0.9893(5) 0.2495(2) 0.05192(18) 0.0514(13) Uani 1 d .
H16 H 0.9874 0.2505 0.0864 0.062 Uiso 1 calc R
C17 C 0.9161(7) 0.1861(3) 0.0354(2) 0.0762(18) Uani 1 d .
H17A H 0.8307 0.1909 0.0448 0.114 Uiso 1 calc R
H17B H 0.9505 0.1445 0.0493 0.114 Uiso 1 calc R
H17C H 0.9207 0.1828 0.0017 0.114 Uiso 1 calc R
C18 C 1.1260(6) 0.2485(4) 0.0361(3) 0.088(2) Uani 1 d .
H18A H 1.1299 0.2424 0.0026 0.132 Uiso 1 calc R
H18B H 1.1685 0.2105 0.0513 0.132 Uiso 1 calc R
H18C H 1.1650 0.2920 0.0445 0.132 Uiso 1 calc R
C19 C 0.7157(5) 0.3127(2) 0.12611(13) 0.0380(11) Uani 1 d .
C20 C 0.6021(5) 0.3434(3) 0.11751(17) 0.0465(12) Uani 1 d .
H20 H 0.5991 0.3916 0.1130 0.056 Uiso 1 calc R
C21 C 0.4934(5) 0.3064(3) 0.11532(17) 0.0551(14) Uani 1 d .
H21 H 0.4192 0.3298 0.1092 0.066 Uiso 1 calc R
C22 C 0.4926(6) 0.2366(3) 0.12186(16) 0.0574(15) Uani 1 d .
H22A H 0.4184 0.2115 0.1203 0.069 Uiso 1 calc R
C23 C 0.6003(7) 0.2038(3) 0.13070(17) 0.0631(17) Uani 1 d .
H23 H 0.6004 0.1555 0.1354 0.076 Uiso 1 calc R
C24 C 0.7115(6) 0.2403(3) 0.13294(17) 0.0583(15) Uani 1 d .
H24 H 0.7849 0.2161 0.1391 0.070 Uiso 1 calc R
C25 C 1.2132(5) 0.4863(2) 0.11966(14) 0.0418(11) Uani 1 d .
C26 C 1.3382(5) 0.4874(3) 0.10668(17) 0.0500(13) Uani 1 d .
H26 H 1.3714 0.4496 0.0903 0.060 Uiso 1 calc R
C27 C 1.4129(5) 0.5428(3) 0.11756(19) 0.0571(13) Uani 1 d .
H27 H 1.4963 0.5422 0.1089 0.069 Uiso 1 calc R
C28 C 1.3660(5) 0.5989(3) 0.1410(2) 0.0600(15) Uani 1 d .
H28 H 1.4161 0.6373 0.1477 0.072 Uiso 1 calc R
C29 C 1.2445(5) 0.5980(3) 0.15447(18) 0.0609(15) Uani 1 d .
H29 H 1.2133 0.6361 0.1712 0.073 Uiso 1 calc R
C30 C 1.1665(5) 0.5433(3) 0.14446(17) 0.0523(13) Uani 1 d .
H30 H 1.0837 0.5443 0.1541 0.063 Uiso 1 calc R
N1 N 0.8024(4) 0.42192(18) 0.22135(12) 0.0423(9) Uani 1 d .
N2 N 0.9047(3) 0.32801(17) 0.22598(12) 0.0360(9) Uani 1 d .
N3 N 0.9289(3) 0.31266(17) 0.03475(12) 0.0371(9) Uani 1 d .
N4 N 0.8313(3) 0.40824(16) 0.03217(11) 0.0316(8) Uani 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.048(2) 0.090(3) 0.046(2) -0.0209(18) 0.0124(16) -0.014(2)
S 0.0525(8) 0.0588(8) 0.0434(8) -0.0020(6) 0.0084(6) 0.0004(6)
Ni 0.0485(5) 0.0326(4) 0.0227(4) -0.0014(2) 0.0008(2) 0.0062(2)
C1 0.044(3) 0.032(2) 0.033(3) -0.0052(19) 0.0004(19) 0.0004(19)
C2 0.069(3) 0.051(3) 0.025(3) -0.010(2) 0.004(2) -0.009(3)
C3 0.059(3) 0.048(3) 0.024(2) -0.001(2) -0.005(2) -0.007(2)
C4 0.046(3) 0.038(2) 0.042(3) 0.002(2) -0.004(2) 0.002(2)
C5 0.054(4) 0.075(4) 0.100(5) -0.025(4) -0.013(3) 0.003(3)
C6 0.102(4) 0.038(3) 0.056(4) 0.005(2) 0.007(3) 0.002(3)
C7 0.109(5) 0.059(3) 0.032(3) -0.010(2) 0.001(3) 0.041(3)
C8 0.097(6) 0.069(4) 0.339(15) 0.108(7) 0.121(8) 0.040(4)
C9 0.048(4) 0.056(4) 0.147(7) 0.014(4) -0.004(4) -0.002(3)
C10 0.034(2) 0.031(2) 0.028(2) -0.0022(18) 0.0041(18) -0.0026(17)
C11 0.052(3) 0.045(3) 0.025(2) -0.008(2) 0.008(2) -0.010(2)
C12 0.052(3) 0.040(3) 0.027(3) 0.003(2) 0.004(2) -0.009(2)
C13 0.046(3) 0.033(2) 0.034(2) 0.0030(19) 0.004(2) 0.007(2)
C14 0.055(3) 0.065(3) 0.053(3) -0.001(3) -0.008(2) 0.015(3)
C15 0.068(4) 0.036(3) 0.073(4) -0.003(2) 0.006(3) 0.000(2)
C16 0.066(3) 0.044(3) 0.045(3) -0.008(2) -0.003(2) 0.021(2)
C17 0.114(5) 0.038(3) 0.076(4) -0.005(3) -0.005(4) 0.012(3)
C18 0.077(5) 0.097(5) 0.091(5) -0.023(4) 0.005(4) 0.040(4)
C19 0.064(3) 0.032(2) 0.019(2) -0.0003(16) 0.0054(19) -0.002(2)
C20 0.051(3) 0.045(3) 0.044(3) 0.003(2) 0.013(2) 0.000(2)
C21 0.056(3) 0.066(4) 0.043(3) 0.002(3) 0.015(3) -0.007(3)
C22 0.070(4) 0.070(4) 0.032(3) -0.004(2) 0.000(2) -0.019(3)
C23 0.104(5) 0.038(3) 0.048(3) -0.001(2) -0.010(3) -0.020(3)
C24 0.084(4) 0.040(3) 0.050(3) 0.000(2) -0.018(3) -0.003(3)
C25 0.051(3) 0.050(3) 0.024(2) 0.010(2) -0.002(2) 0.005(2)
C26 0.056(3) 0.053(3) 0.042(3) 0.004(2) 0.009(2) 0.006(3)
C27 0.055(3) 0.064(3) 0.053(3) 0.005(3) 0.012(3) -0.003(3)
C28 0.068(4) 0.059(4) 0.052(3) -0.002(3) -0.001(3) -0.011(3)
C29 0.077(4) 0.057(3) 0.049(3) -0.010(3) -0.010(3) 0.010(3)
C30 0.053(3) 0.069(4) 0.034(3) -0.002(3) -0.005(2) 0.015(3)
N1 0.064(3) 0.038(2) 0.026(2) -0.0029(16) 0.0002(18) 0.0037(18)
N2 0.048(2) 0.034(2) 0.0254(19) 0.0005(16) -0.0038(16) -0.0050(17)
N3 0.045(2) 0.0329(19) 0.033(2) -0.0063(16) 0.0055(17) 0.0024(16)
N4 0.0379(19) 0.0349(19) 0.0220(19) 0.0020(15) 0.0014(15) -0.0022(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O S 1.593(4)
O Ni 1.937(4)
S C25 1.731(5)
Ni C19 1.898(5)
Ni C1 1.903(5)
Ni C10 1.917(4)
C1 N2 1.343(5)
C1 N1 1.358(5)
C2 C3 1.322(7)
C2 N1 1.375(6)
C3 N2 1.394(5)
C4 N2 1.471(5)
C4 C5 1.503(7)
C4 C6 1.511(6)
C7 N1 1.458(6)
C7 C9 1.488(8)
C7 C8 1.506(9)
C10 N4 1.344(5)
C10 N3 1.351(5)
C11 C12 1.322(6)
C11 N3 1.371(5)
C12 N4 1.369(5)
C13 N4 1.471(5)
C13 C14 1.496(7)
C13 C15 1.502(6)
C16 N3 1.468(6)
C16 C17 1.534(7)
C16 C18 1.553(8)
C19 C20 1.391(7)
C19 C24 1.411(7)
C20 C21 1.380(7)
C21 C22 1.360(7)
C22 C23 1.354(8)
C23 C24 1.401(9)
C25 C30 1.405(7)
C25 C26 1.408(7)
C26 C27 1.377(7)
C27 C28 1.371(8)
C28 C29 1.375(7)
C29 C30 1.384(7)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
S O Ni 119.3(2)
O S C25 102.9(2)
C19 Ni C1 90.67(17)
C19 Ni C10 89.31(16)
C1 Ni C10 179.98(16)
C19 Ni O 172.58(17)
C1 Ni O 85.70(16)
C10 Ni O 94.32(15)
N2 C1 N1 104.0(4)
N2 C1 Ni 127.2(3)
N1 C1 Ni 128.3(3)
C3 C2 N1 106.6(4)
C2 C3 N2 107.3(4)
N2 C4 C5 109.7(4)
N2 C4 C6 110.5(4)
C5 C4 C6 113.2(5)
N1 C7 C9 111.9(5)
N1 C7 C8 110.2(5)
C9 C7 C8 110.1(5)
N4 C10 N3 104.3(4)
N4 C10 Ni 125.6(3)
N3 C10 Ni 130.1(3)
C12 C11 N3 107.7(4)
C11 C12 N4 106.5(4)
N4 C13 C14 110.2(4)
N4 C13 C15 110.1(4)
C14 C13 C15 112.8(4)
N3 C16 C17 109.0(4)
N3 C16 C18 109.9(5)
C17 C16 C18 113.3(5)
C20 C19 C24 114.7(5)
C20 C19 Ni 121.7(3)
C24 C19 Ni 123.6(4)
C21 C20 C19 123.2(5)
C22 C21 C20 120.8(5)
C23 C22 C21 118.9(5)
C22 C23 C24 121.2(5)
C23 C24 C19 121.3(6)
C30 C25 C26 118.0(5)
C30 C25 S 122.0(4)
C26 C25 S 120.0(4)
C27 C26 C25 121.3(5)
C28 C27 C26 120.3(5)
C27 C28 C29 119.0(5)
C28 C29 C30 122.6(5)
C29 C30 C25 118.7(5)
C1 N1 C2 111.5(4)
C1 N1 C7 123.7(4)
C2 N1 C7 124.8(4)
C1 N2 C3 110.6(4)
C1 N2 C4 123.5(4)
C3 N2 C4 125.8(4)
C10 N3 C11 110.2(4)
C10 N3 C16 124.6(4)
C11 N3 C16 125.2(4)
C10 N4 C12 111.3(4)
C10 N4 C13 123.4(3)
C12 N4 C13 125.2(4)
_cod_database_code 7101897
_journal_paper_doi 10.1039/b924423a