#------------------------------------------------------------------------------
#$Date: 2018-09-07 11:23:34 +0300 (Fri, 07 Sep 2018) $
#$Revision: 210514 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/18/7101895.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_7101895
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_coden_ASTM              CHCOFS
_journal_issue                   20
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2037
_journal_page_last               2039
_journal_paper_doi               10.1039/b618632g
_journal_year                    2007
_chemical_formula_sum            'C27 H46 N4 Ni O S'
_chemical_formula_weight         533.45
_chemical_name_common
;Bis-(1,3-di(isopropyl)imidazol-2-
ylidene)(methylsulfoxyl)(methyl)nickel(ii)
;
_chemical_name_systematic
;
Bis-{1,3-di(isopropyl)imidazol-2-ylidene)(methylsulfoxyl)(methyl)nickel(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.695(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9991(6)
_cell_length_b                   12.2314(5)
_cell_length_c                   27.8178(18)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      24.90
_cell_measurement_theta_min      1.85
_cell_volume                     3055.6(3)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11807
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.057
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0400
_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)+(0.0646P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                3852
_reflns_number_total             5239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b618632g.txt
_cod_data_source_block           compound2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.0000P] 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^)+(0.0646P)^2^+0.0000P] 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      P2(1)/n
_cod_database_code               7101895
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_calc_flag
_atom_site_refinement_flags
O O 1.1552(2) 0.77168(19) 0.19460(9) 0.0557(6) Uani 1 d .
S S 1.01497(7) 0.70878(6) 0.17634(3) 0.03883(18) Uani 1 d .
Ni Ni 0.86308(3) 0.79338(3) 0.123449(11) 0.02729(12) Uani 1 d .
C1 C 0.6954(3) 0.7131(2) 0.14099(9) 0.0292(5) Uani 1 d .
C2 C 0.4704(3) 0.6704(2) 0.16798(11) 0.0403(7) Uani 1 d .
H2 H 0.3798 0.6773 0.1827 0.048 Uiso 1 calc R
C3 C 0.5190(3) 0.5826(2) 0.14537(11) 0.0387(7) Uani 1 d .
H3 H 0.4692 0.5154 0.1413 0.046 Uiso 1 calc R
C4 C 0.7451(3) 0.5368(2) 0.10000(12) 0.0455(7) Uani 1 d .
H4 H 0.8411 0.5735 0.0951 0.055 Uiso 1 calc R
C5 C 0.6643(6) 0.5187(4) 0.05089(15) 0.0830(13) Uani 1 d .
H5A H 0.5739 0.4772 0.0547 0.125 Uiso 1 calc R
H5B H 0.7283 0.4785 0.0304 0.125 Uiso 1 calc R
H5C H 0.6390 0.5888 0.0363 0.125 Uiso 1 calc R
C6 C 0.7774(4) 0.4296(3) 0.12584(15) 0.0574(9) Uani 1 d .
H6A H 0.8276 0.4439 0.1571 0.086 Uiso 1 calc R
H6B H 0.8407 0.3848 0.1069 0.086 Uiso 1 calc R
H6C H 0.6846 0.3915 0.1300 0.086 Uiso 1 calc R
C7 C 0.5719(3) 0.8602(2) 0.18615(11) 0.0393(6) Uani 1 d .
H7 H 0.6693 0.8966 0.1836 0.047 Uiso 1 calc R
C8 C 0.5399(5) 0.8540(3) 0.23845(13) 0.0690(10) Uani 1 d .
H8A H 0.4431 0.8208 0.2414 0.104 Uiso 1 calc R
H8B H 0.5403 0.9271 0.2520 0.104 Uiso 1 calc R
H8C H 0.6158 0.8102 0.2557 0.104 Uiso 1 calc R
C9 C 0.4539(4) 0.9263(3) 0.15780(15) 0.0620(10) Uani 1 d .
H9A H 0.4754 0.9273 0.1241 0.093 Uiso 1 calc R
H9B H 0.4538 1.0006 0.1701 0.093 Uiso 1 calc R
H9C H 0.3570 0.8935 0.1611 0.093 Uiso 1 calc R
C10 C 1.0137(2) 0.8894(2) 0.10537(9) 0.0291(5) Uani 1 d .
C11 C 1.1849(3) 0.9800(3) 0.06508(11) 0.0436(7) Uani 1 d .
H11 H 1.2537 0.9961 0.0421 0.052 Uiso 1 calc R
C12 C 1.1481(3) 1.0439(2) 0.10125(11) 0.0414(7) Uani 1 d .
H12 H 1.1862 1.1139 0.1086 0.050 Uiso 1 calc R
C13 C 0.9748(3) 1.0270(2) 0.16880(12) 0.0463(7) Uani 1 d .
H13 H 0.9136 0.9664 0.1804 0.056 Uiso 1 calc R
C14 C 0.8719(5) 1.1211(4) 0.15672(17) 0.0904(15) Uani 1 d .
H14A H 0.9291 1.1830 0.1463 0.136 Uiso 1 calc R
H14B H 0.8205 1.1413 0.1850 0.136 Uiso 1 calc R
H14C H 0.7996 1.0998 0.1311 0.136 Uiso 1 calc R
C15 C 1.0919(4) 1.0539(3) 0.20883(14) 0.0685(10) Uani 1 d .
H15A H 1.1585 0.9921 0.2141 0.103 Uiso 1 calc R
H15B H 1.0436 1.0695 0.2382 0.103 Uiso 1 calc R
H15C H 1.1484 1.1173 0.1998 0.103 Uiso 1 calc R
C16 C 1.1163(3) 0.7870(3) 0.03785(11) 0.0479(7) Uani 1 d .
H16 H 1.0294 0.7392 0.0422 0.057 Uiso 1 calc R
C17 C 1.1159(6) 0.8164(4) -0.01462(14) 0.0878(14) Uani 1 d .
H17A H 1.0305 0.8623 -0.0233 0.132 Uiso 1 calc R
H17B H 1.1102 0.7502 -0.0339 0.132 Uiso 1 calc R
H17C H 1.2066 0.8556 -0.0205 0.132 Uiso 1 calc R
C18 C 1.2549(5) 0.7248(4) 0.05444(16) 0.0837(14) Uani 1 d .
H18A H 1.3420 0.7683 0.0486 0.126 Uiso 1 calc R
H18B H 1.2586 0.6566 0.0368 0.126 Uiso 1 calc R
H18C H 1.2533 0.7094 0.0886 0.126 Uiso 1 calc R
C19 C 0.7388(3) 0.8529(3) 0.06723(11) 0.0456(7) Uani 1 d .
H19A H 0.7172 0.9294 0.0728 0.068 Uiso 1 calc R
H19B H 0.6464 0.8122 0.0633 0.068 Uiso 1 calc R
H19C H 0.7927 0.8461 0.0383 0.068 Uiso 1 calc R
C20 C 0.9196(4) 0.6873(3) 0.23045(13) 0.0616(10) Uani 1 d .
H20A H 0.9842 0.6480 0.2538 0.092 Uiso 1 calc R
H20B H 0.8300 0.6449 0.2230 0.092 Uiso 1 calc R
H20C H 0.8931 0.7574 0.2438 0.092 Uiso 1 calc R
C21 C 0.3110(4) 0.3346(3) 0.17844(15) 0.0607(9) Uani 1 d .
H21 H 0.3238 0.3260 0.2120 0.073 Uiso 1 calc R
C22 C 0.1871(4) 0.4167(4) 0.1100(2) 0.0950(17) Uani 1 d .
H22 H 0.1155 0.4658 0.0967 0.114 Uiso 1 calc R
C23 C 0.2715(4) 0.3545(4) 0.08013(17) 0.0839(15) Uani 1 d .
H23 H 0.2558 0.3619 0.0465 0.101 Uiso 1 calc R
C24 C 0.4713(5) 0.2161(4) 0.06681(17) 0.0857(14) Uani 1 d .
H24A H 0.4135 0.1988 0.0371 0.129 Uiso 1 calc R
H24B H 0.5021 0.1489 0.0831 0.129 Uiso 1 calc R
H24C H 0.5586 0.2579 0.0595 0.129 Uiso 1 calc R
C25 C 0.2083(4) 0.4066(4) 0.15904(18) 0.0793(13) Uani 1 d .
H25 H 0.1519 0.4493 0.1793 0.095 Uiso 1 calc R
C26 C 0.3959(4) 0.2743(3) 0.14854(13) 0.0538(8) Uani 1 d .
H26 H 0.4683 0.2265 0.1624 0.065 Uiso 1 calc R
C27 C 0.3783(4) 0.2819(3) 0.09873(14) 0.0585(9) Uani 1 d .
N1 N 0.5801(2) 0.74952(18) 0.16540(8) 0.0307(5) Uani 1 d .
N2 N 0.6565(2) 0.60874(17) 0.12895(8) 0.0338(5) Uani 1 d .
N3 N 1.1016(2) 0.88505(19) 0.06808(8) 0.0355(5) Uani 1 d .
N4 N 1.0439(2) 0.98812(17) 0.12593(8) 0.0341(5) Uani 1 d .
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O S C20 102.87(15)
O S Ni 116.56(9)
C20 S Ni 108.58(12)
C10 Ni C1 172.54(10)
C10 Ni C19 86.55(11)
C1 Ni C19 88.62(11)
C10 Ni S 92.58(8)
C1 Ni S 93.14(8)
C19 Ni S 170.26(10)
N1 C1 N2 103.9(2)
N1 C1 Ni 127.54(19)
N2 C1 Ni 128.43(19)
C3 C2 N1 106.3(2)
C2 C3 N2 107.3(2)
N2 C4 C6 110.7(3)
N2 C4 C5 109.6(3)
C6 C4 C5 111.4(3)
N1 C7 C8 110.5(2)
N1 C7 C9 109.7(2)
C8 C7 C9 111.1(3)
N3 C10 N4 104.4(2)
N3 C10 Ni 130.47(19)
N4 C10 Ni 124.74(19)
C12 C11 N3 106.5(2)
C11 C12 N4 107.2(2)
N4 C13 C14 110.8(3)
N4 C13 C15 111.0(3)
C14 C13 C15 112.8(3)
N3 C16 C17 111.4(3)
N3 C16 C18 109.8(3)
C17 C16 C18 111.6(3)
C25 C21 C26 119.6(4)
C25 C22 C23 120.0(4)
C27 C23 C22 121.4(4)
C21 C25 C22 120.0(4)
C21 C26 C27 122.3(4)
C23 C27 C26 116.6(4)
C23 C27 C24 121.7(4)
C26 C27 C24 121.7(4)
C1 N1 C2 111.6(2)
C1 N1 C7 123.9(2)
C2 N1 C7 124.5(2)
C1 N2 C3 110.9(2)
C1 N2 C4 124.0(2)
C3 N2 C4 125.0(2)
C10 N3 C11 111.1(2)
C10 N3 C16 123.4(2)
C11 N3 C16 125.3(2)
C10 N4 C12 110.8(2)
C10 N4 C13 123.4(2)
C12 N4 C13 125.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O S 1.536(2)
S C20 1.800(4)
S Ni 2.2010(8)
Ni C10 1.886(2)
Ni C1 1.891(2)
Ni C19 2.000(3)
C1 N1 1.352(3)
C1 N2 1.359(3)
C2 C3 1.333(4)
C2 N1 1.388(3)
C3 N2 1.384(3)
C4 N2 1.463(4)
C4 C6 1.515(5)
C4 C5 1.522(5)
C7 N1 1.476(3)
C7 C8 1.503(5)
C7 C9 1.515(4)
C10 N3 1.346(3)
C10 N4 1.356(3)
C11 C12 1.332(4)
C11 N3 1.387(4)
C12 N4 1.379(3)
C13 N4 1.459(4)
C13 C14 1.502(5)
C13 C15 1.519(5)
C16 N3 1.476(4)
C16 C17 1.503(5)
C16 C18 1.508(5)
C21 C25 1.363(5)
C21 C26 1.379(5)
C22 C25 1.369(7)
C22 C23 1.389(7)
C23 C27 1.384(6)
C24 C27 1.494(6)
C26 C27 1.387(5)
