#------------------------------------------------------------------------------
#$Date: 2017-07-11 15:10:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/59/4065995.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_4065995
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            'C32 H44 N6 Ni S2'
_chemical_formula_weight         635.56
_chemical_name_systematic
; 
 ? 
;
_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                103.240(2)
_cell_angle_beta                 94.178(2)
_cell_angle_gamma                113.049(2)
_cell_formula_units_Z            1
_cell_length_a                   9.3168(7)
_cell_length_b                   10.0285(8)
_cell_length_c                   10.3736(8)
_cell_measurement_reflns_used    2398
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.03
_cell_measurement_theta_min      2.30
_cell_volume                     853.75(12)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11224
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.8935
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs,(Sheldrick 2001)'
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3910
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0573
_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)+(0.0862P)²+0.1923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                3246
_reflns_number_total             3910
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100241v_si_002.cif
_cod_data_source_block           trans-2b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        853.75(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4065995
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
Ni1 Ni 0.5000 0.0000 0.5000 0.03953(18) Uani 1 2 d S . .
S1 S 0.34427(12) 0.22923(13) 0.21678(10) 0.0788(3) Uani 1 1 d . . .
N1 N 0.8353(3) 0.1315(2) 0.4692(2) 0.0451(5) Uani 1 1 d . . .
N2 N 0.7783(3) 0.2900(2) 0.6116(2) 0.0451(5) Uani 1 1 d . B .
N3 N 0.4331(3) 0.1001(3) 0.3963(3) 0.0527(6) Uani 1 1 d . . .
C1 C 0.7147(3) 0.1484(3) 0.5266(2) 0.0426(6) Uani 1 1 d . . .
C2 C 0.9761(3) 0.2608(3) 0.5212(3) 0.0473(6) Uani 1 1 d . . .
C3 C 1.1309(4) 0.2961(4) 0.4985(3) 0.0605(8) Uani 1 1 d . . .
H3 H 1.1559 0.2285 0.4372 0.073 Uiso 1 1 calc R . .
C4 C 1.2447(4) 0.4357(4) 0.5711(4) 0.0694(9) Uani 1 1 d . . .
H4 H 1.3493 0.4629 0.5590 0.083 Uiso 1 1 calc R . .
C5 C 1.2075(4) 0.5375(4) 0.6622(4) 0.0698(9) Uani 1 1 d . . .
H5 H 1.2878 0.6307 0.7099 0.084 Uiso 1 1 calc R . .
C6 C 1.0553(4) 0.5036(3) 0.6834(3) 0.0601(8) Uani 1 1 d . . .
H6 H 1.0302 0.5722 0.7432 0.072 Uiso 1 1 calc R . .
C7 C 0.9400(3) 0.3620(3) 0.6115(3) 0.0469(6) Uani 1 1 d . . .
C8 C 0.8240(4) -0.0039(3) 0.3715(3) 0.0549(7) Uani 1 1 d . . .
H8A H 0.7198 -0.0846 0.3619 0.066 Uiso 1 1 calc R . .
H8B H 0.9020 -0.0352 0.4053 0.066 Uiso 1 1 calc R . .
C9 C 0.8514(5) 0.0197(5) 0.2312(4) 0.0844(12) Uani 1 1 d . . .
H9 H 0.9515 0.1086 0.2436 0.101 Uiso 1 1 calc R . .
C10 C 0.8718(8) -0.1212(7) 0.1520(5) 0.138(2) Uani 1 1 d . . .
H10A H 0.7798 -0.2108 0.1487 0.207 Uiso 1 1 calc R . .
H10B H 0.9641 -0.1243 0.1962 0.207 Uiso 1 1 calc R . .
H10C H 0.8840 -0.1156 0.0620 0.207 Uiso 1 1 calc R . .
C11 C 0.7271(7) 0.0431(6) 0.1595(4) 0.1095(17) Uani 1 1 d . . .
H11A H 0.7573 0.0662 0.0780 0.164 Uiso 1 1 calc R . .
H11B H 0.7118 0.1254 0.2153 0.164 Uiso 1 1 calc R . .
H11C H 0.6301 -0.0470 0.1379 0.164 Uiso 1 1 calc R . .
C12 C 0.6910(4) 0.3558(3) 0.6963(3) 0.0555(7) Uani 1 1 d D . .
H12A H 0.5918 0.3351 0.6413 0.067 Uiso 1 1 calc R A 1
H12B H 0.7518 0.4645 0.7252 0.067 Uiso 1 1 calc R A 1
C13 C 0.6535(9) 0.3029(9) 0.8199(6) 0.073(2) Uani 0.50 1 d PD B 1
H13 H 0.5846 0.1946 0.7959 0.087 Uiso 0.50 1 calc PR B 1
C14 C 0.8132(11) 0.3408(16) 0.9048(10) 0.108(4) Uani 0.50 1 d PD B 1
H14A H 0.7957 0.3103 0.9856 0.162 Uiso 0.50 1 calc PR B 1
H14B H 0.8771 0.4477 0.9279 0.162 Uiso 0.50 1 calc PR B 1
H14C H 0.8669 0.2884 0.8541 0.162 Uiso 0.50 1 calc PR B 1
C15 C 0.5700(19) 0.3976(19) 0.8883(12) 0.106(5) Uani 0.50 1 d PD B 1
H15A H 0.5416 0.3715 0.9691 0.160 Uiso 0.50 1 calc PR B 1
H15B H 0.4761 0.3777 0.8281 0.160 Uiso 0.50 1 calc PR B 1
H15C H 0.6403 0.5029 0.9102 0.160 Uiso 0.50 1 calc PR B 1
C13A C 0.7494(11) 0.3829(8) 0.8478(5) 0.073(2) Uani 0.50 1 d PD B 2
H13A H 0.8578 0.4626 0.8703 0.088 Uiso 0.50 1 calc PR B 2
C14A C 0.7585(15) 0.2484(10) 0.8885(11) 0.091(3) Uani 0.50 1 d PD B 2
H14D H 0.8232 0.2123 0.8359 0.137 Uiso 0.50 1 calc PR B 2
H14E H 0.6537 0.1691 0.8728 0.137 Uiso 0.50 1 calc PR B 2
H14F H 0.8041 0.2796 0.9823 0.137 Uiso 0.50 1 calc PR B 2
C15A C 0.652(2) 0.443(2) 0.9386(12) 0.130(8) Uani 0.50 1 d PD B 2
H15D H 0.6455 0.5275 0.9150 0.195 Uiso 0.50 1 calc PR B 2
H15E H 0.7030 0.4735 1.0310 0.195 Uiso 0.50 1 calc PR B 2
H15F H 0.5475 0.3644 0.9265 0.195 Uiso 0.50 1 calc PR B 2
C16 C 0.3960(3) 0.1519(3) 0.3222(3) 0.0501(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 180.0 2_656 .
N3 Ni1 C1 89.98(10) 2_656 2_656
N3 Ni1 C1 90.03(10) . 2_656
N3 Ni1 C1 90.03(10) 2_656 .
N3 Ni1 C1 89.97(10) . .
C1 Ni1 C1 180.0 2_656 .
C1 N1 C2 110.5(2) . .
C1 N1 C8 125.9(2) . .
C2 N1 C8 123.6(2) . .
C1 N2 C7 110.8(2) . .
C1 N2 C12 124.7(2) . .
C7 N2 C12 124.5(2) . .
C16 N3 Ni1 172.7(3) . .
N2 C1 N1 105.9(2) . .
N2 C1 Ni1 126.64(19) . .
N1 C1 Ni1 127.42(19) . .
C7 C2 N1 106.6(2) . .
C7 C2 C3 121.2(3) . .
N1 C2 C3 132.1(3) . .
C4 C3 C2 116.7(3) . .
C3 C4 C5 121.8(3) . .
C6 C5 C4 121.5(3) . .
C5 C6 C7 117.0(3) . .
C2 C7 C6 121.7(3) . .
C2 C7 N2 106.2(2) . .
C6 C7 N2 132.1(3) . .
N1 C8 C9 113.0(3) . .
C11 C9 C8 114.5(4) . .
C11 C9 C10 112.2(4) . .
C8 C9 C10 105.4(4) . .
N2 C12 C13 116.8(3) . .
N2 C12 C13A 111.5(3) . .
C13 C12 C13A 34.4(4) . .
C12 C13 C14 106.2(6) . .
C12 C13 C15 103.5(7) . .
C14 C13 C15 112.2(9) . .
C14A C13A C15A 108.1(10) . .
C14A C13A C12 116.3(6) . .
C15A C13A C12 112.5(7) . .
N3 C16 S1 179.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N3 1.854(3) 2_656
Ni1 N3 1.855(3) .
Ni1 C1 1.921(3) 2_656
Ni1 C1 1.921(3) .
S1 C16 1.623(3) .
N1 C1 1.359(3) .
N1 C2 1.392(3) .
N1 C8 1.458(3) .
N2 C1 1.355(3) .
N2 C7 1.393(3) .
N2 C12 1.459(3) .
N3 C16 1.125(4) .
C2 C7 1.378(4) .
C2 C3 1.396(4) .
C3 C4 1.375(5) .
C4 C5 1.393(5) .
C5 C6 1.370(5) .
C6 C7 1.389(4) .
C8 C9 1.551(5) .
C9 C11 1.454(6) .
C9 C10 1.552(6) .
C12 C13 1.510(4) .
C12 C13A 1.550(5) .
C13 C14 1.532(5) .
C13 C15 1.536(5) .
C13A C14A 1.533(5) .
C13A C15A 1.536(5) .
