#------------------------------------------------------------------------------
#$Date: 2017-07-11 15:10:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/59/4065996.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_4065996
loop_
_publ_author_name
'Jothibasu, Ramasamy'
'Huang, Kuo-Wei'
'Huynh, Han Vinh'
_publ_section_title
;
 Synthesis ofcis- andtrans-Diisothiocyanato−Bis(NHC) Complexes of
 Nickel(II) and Applications in the Kumada−Corriu Reaction
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              3746
_journal_paper_doi               10.1021/om100241v
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C44 H36 N6 Ni S2'
_chemical_formula_weight         771.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 106.050(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6333(11)
_cell_length_b                   18.7005(16)
_cell_length_c                   8.4257(7)
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      21.73
_cell_measurement_theta_min      2.74
_cell_volume                     1913.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13453
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.9372
_exptl_absorpt_correction_T_min  0.6217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0678P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                3242
_reflns_number_total             4388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100241v_si_002.cif
_cod_data_source_block           trans-2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'contr' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4065996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni1 Ni 1.0000 0.0000 0.0000 0.02657(15) Uani 1 2 d S
S1 S 1.18571(6) 0.03327(4) 0.54585(9) 0.0456(2) Uani 1 1 d .
N1 N 1.02107(16) 0.15473(10) -0.0542(2) 0.0282(5) Uani 1 1 d .
N2 N 0.87964(16) 0.12964(11) 0.0330(2) 0.0288(5) Uani 1 1 d .
N3 N 1.05865(18) 0.00811(11) 0.2258(3) 0.0339(5) Uani 1 1 d .
C1 C 0.9650(2) 0.09986(13) -0.0106(3) 0.0280(5) Uani 1 1 d .
C2 C 0.9720(2) 0.22010(13) -0.0374(3) 0.0287(5) Uani 1 1 d .
C3 C 1.0000(2) 0.29035(14) -0.0616(3) 0.0362(6) Uani 1 1 d .
H3 H 1.0629 0.3016 -0.0956 0.043 Uiso 1 1 calc R
C4 C 0.9304(2) 0.34289(14) -0.0331(3) 0.0421(7) Uani 1 1 d .
H4 H 0.9465 0.3911 -0.0481 0.050 Uiso 1 1 calc R
C5 C 0.8382(3) 0.32654(15) 0.0169(3) 0.0444(7) Uani 1 1 d .
H5 H 0.7928 0.3640 0.0336 0.053 Uiso 1 1 calc R
C6 C 0.8101(2) 0.25661(15) 0.0434(3) 0.0401(7) Uani 1 1 d .
H6 H 0.7471 0.2456 0.0775 0.048 Uiso 1 1 calc R
C7 C 0.8807(2) 0.20379(13) 0.0164(3) 0.0306(6) Uani 1 1 d .
C8 C 1.1169(2) 0.14667(14) -0.1196(3) 0.0340(6) Uani 1 1 d .
H8A H 1.1078 0.1786 -0.2146 0.041 Uiso 1 1 calc R
H8B H 1.1186 0.0975 -0.1591 0.041 Uiso 1 1 calc R
C9 C 1.2254(2) 0.16279(13) 0.0040(3) 0.0319(6) Uani 1 1 d .
C10 C 1.2707(2) 0.11530(16) 0.1290(4) 0.0453(7) Uani 1 1 d .
H10 H 1.2322 0.0734 0.1397 0.054 Uiso 1 1 calc R
C11 C 1.3720(3) 0.1287(2) 0.2386(4) 0.0587(9) Uani 1 1 d .
H11 H 1.4024 0.0955 0.3226 0.070 Uiso 1 1 calc R
C12 C 1.4282(2) 0.1893(2) 0.2262(4) 0.0598(9) Uani 1 1 d .
H12 H 1.4967 0.1984 0.3026 0.072 Uiso 1 1 calc R
C13 C 1.3853(3) 0.23710(19) 0.1028(5) 0.0634(10) Uani 1 1 d .
H13 H 1.4245 0.2789 0.0938 0.076 Uiso 1 1 calc R
C14 C 1.2836(2) 0.22410(16) -0.0095(4) 0.0512(8) Uani 1 1 d .
H14 H 1.2543 0.2570 -0.0947 0.061 Uiso 1 1 calc R
C15 C 0.7946(2) 0.08954(14) 0.0820(3) 0.0343(6) Uani 1 1 d .
H15A H 0.7822 0.1117 0.1808 0.041 Uiso 1 1 calc R
H15B H 0.8208 0.0407 0.1111 0.041 Uiso 1 1 calc R
C16 C 0.6864(2) 0.08650(13) -0.0515(3) 0.0320(6) Uani 1 1 d .
C17 C 0.5887(2) 0.08998(18) -0.0106(4) 0.0535(8) Uani 1 1 d .
H17 H 0.5895 0.0964 0.1004 0.064 Uiso 1 1 calc R
C18 C 0.4893(3) 0.0841(2) -0.1303(5) 0.0649(10) Uani 1 1 d .
H18 H 0.4230 0.0864 -0.1003 0.078 Uiso 1 1 calc R
C19 C 0.4869(2) 0.07513(17) -0.2921(4) 0.0557(9) Uani 1 1 d .
H19 H 0.4191 0.0712 -0.3734 0.067 Uiso 1 1 calc R
C20 C 0.5832(2) 0.07176(17) -0.3357(4) 0.0533(8) Uani 1 1 d .
H20 H 0.5819 0.0659 -0.4471 0.064 Uiso 1 1 calc R
C21 C 0.6831(2) 0.07696(16) -0.2150(4) 0.0429(7) Uani 1 1 d .
H21 H 0.7493 0.0739 -0.2452 0.051 Uiso 1 1 calc R
C22 C 1.1106(2) 0.01907(13) 0.3586(3) 0.0298(6) Uani 1 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'
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
N3 Ni1 N3 179.998(1) 3_755 .
N3 Ni1 C1 90.60(9) 3_755 .
N3 Ni1 C1 89.40(9) . .
N3 Ni1 C1 89.40(9) 3_755 3_755
N3 Ni1 C1 90.60(9) . 3_755
C1 Ni1 C1 179.999(1) . 3_755
C1 N1 C2 110.8(2) . .
C1 N1 C8 124.8(2) . .
C2 N1 C8 124.3(2) . .
C1 N2 C7 110.6(2) . .
C1 N2 C15 124.8(2) . .
C7 N2 C15 124.6(2) . .
C22 N3 Ni1 167.6(2) . .
N2 C1 N1 106.2(2) . .
N2 C1 Ni1 125.47(18) . .
N1 C1 Ni1 128.30(19) . .
C7 C2 C3 121.7(2) . .
C7 C2 N1 105.9(2) . .
C3 C2 N1 132.4(2) . .
C4 C3 C2 116.5(3) . .
C5 C4 C3 121.8(3) . .
C4 C5 C6 122.2(3) . .
C5 C6 C7 116.0(3) . .
C2 C7 C6 121.8(2) . .
C2 C7 N2 106.5(2) . .
C6 C7 N2 131.7(2) . .
N1 C8 C9 114.0(2) . .
C10 C9 C14 118.7(3) . .
C10 C9 C8 120.4(2) . .
C14 C9 C8 120.8(2) . .
C9 C10 C11 120.6(3) . .
C12 C11 C10 120.6(3) . .
C11 C12 C13 120.0(3) . .
C12 C13 C14 120.1(3) . .
C9 C14 C13 120.0(3) . .
N2 C15 C16 113.1(2) . .
C17 C16 C21 118.5(3) . .
C17 C16 C15 120.1(3) . .
C21 C16 C15 121.3(2) . .
C16 C17 C18 120.8(3) . .
C19 C18 C17 120.3(3) . .
C18 C19 C20 119.9(3) . .
C19 C20 C21 119.8(3) . .
C16 C21 C20 120.8(3) . .
N3 C22 S1 178.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N3 1.848(2) 3_755
Ni1 N3 1.848(2) .
Ni1 C1 1.915(2) .
Ni1 C1 1.916(2) 3_755
S1 C22 1.622(3) .
N1 C1 1.354(3) .
N1 C2 1.396(3) .
N1 C8 1.469(3) .
N2 C1 1.352(3) .
N2 C7 1.394(3) .
N2 C15 1.461(3) .
N3 C22 1.148(3) .
C2 C7 1.385(3) .
C2 C3 1.390(3) .
C3 C4 1.383(4) .
C4 C5 1.378(4) .
C5 C6 1.389(4) .
C6 C7 1.391(3) .
C8 C9 1.505(4) .
C9 C10 1.375(4) .
C9 C14 1.383(4) .
C10 C11 1.378(4) .
C11 C12 1.358(5) .
C12 C13 1.364(5) .
C13 C14 1.391(4) .
C15 C16 1.512(3) .
C16 C17 1.372(4) .
C16 C21 1.379(4) .
C17 C18 1.381(4) .
C18 C19 1.366(5) .
C19 C20 1.366(4) .
C20 C21 1.388(4) .
