#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:53:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178586 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/97/4069765.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_4069765
loop_
_publ_author_name
'Huang, Yi-Ping'
'Tsai, Chung-Chih'
'Shih, Wei-Chih'
'Chang, Yu-Chang'
'Lin, Shen-Ta'
'Yap, Glenn P. A.'
'Chao, Ito'
'Ong, Tiow-Gan'
_publ_section_title
;
 Kinetic and Thermodynamic Study ofSyn−AntiIsomerization of Nickel
 Complexes Bearing Amino-Linked N-Heterocyclic Carbene Ligands: The Effect
 of the Pendant Arm of the NHC
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              4316
_journal_paper_doi               10.1021/om900404c
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C36 H62 Cl2 N6 Ni O4'
_chemical_formula_weight         772.53
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 120.970(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.7199(9)
_cell_length_b                   17.7955(8)
_cell_length_c                   15.5740(7)
_cell_measurement_reflns_used    7578
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      2.54
_cell_volume                     4448.5(4)
_computing_cell_refinement       'SHELXTL, Sheldrick (2001)'
_computing_data_collection       'SMART, Bruker (2002)'
_computing_data_reduction        'SHELXTL, Sheldrick (2001)'
_computing_molecular_graphics    'SHELXTL, Sheldrick (2001)'
_computing_publication_material  'SHELXTL, Sheldrick (2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_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  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43810
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.9428
_exptl_absorpt_correction_T_min  0.9212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2003)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0989P)²+3.3344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1752
_reflns_number_gt                3395
_reflns_number_total             4902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900404c_si_004.cif
_cod_data_source_block           i10308
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4069765
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni Ni 0.0000 0.07585(3) 0.7500 0.02787(19) Uani 1 2 d S
Cl Cl 0.10933(4) 0.07108(4) 0.90182(5) 0.0346(2) Uani 1 1 d .
N1 N 0.11961(15) 0.13467(14) 0.69682(17) 0.0325(6) Uani 1 1 d .
N2 N 0.08373(15) 0.02152(14) 0.64478(17) 0.0357(6) Uani 1 1 d .
N3 N 0.1396(2) -0.10251(18) 0.7957(2) 0.0501(8) Uani 1 1 d .
H3 H 0.134(2) -0.050(2) 0.809(3) 0.060 Uiso 1 1 d .
C1 C 0.20237(18) 0.22358(18) 0.8304(2) 0.0345(7) Uani 1 1 d .
C2 C 0.2131(2) 0.29567(18) 0.8704(2) 0.0378(7) Uani 1 1 d .
H2A H 0.2615 0.3068 0.9306 0.045 Uiso 1 1 calc R
C3 C 0.1532(2) 0.35105(18) 0.8226(2) 0.0396(7) Uani 1 1 d .
C4 C 0.0818(2) 0.33306(18) 0.7323(2) 0.0400(7) Uani 1 1 d .
H4A H 0.0418 0.3701 0.6990 0.048 Uiso 1 1 calc R
C5 C 0.06784(19) 0.26229(17) 0.6899(2) 0.0369(7) Uani 1 1 d .
C6 C 0.12886(18) 0.20782(17) 0.7411(2) 0.0318(7) Uani 1 1 d .
C7 C 0.2705(2) 0.16612(19) 0.8830(2) 0.0423(8) Uani 1 1 d .
H7A H 0.3129 0.1857 0.9464 0.063 Uiso 1 1 calc R
H7B H 0.2942 0.1549 0.8426 0.063 Uiso 1 1 calc R
H7C H 0.2477 0.1211 0.8935 0.063 Uiso 1 1 calc R
C8 C 0.1652(3) 0.42863(19) 0.8657(3) 0.0544(10) Uani 1 1 d .
H8A H 0.2183 0.4316 0.9267 0.082 Uiso 1 1 calc R
H8B H 0.1218 0.4393 0.8795 0.082 Uiso 1 1 calc R
H8C H 0.1632 0.4646 0.8186 0.082 Uiso 1 1 calc R
C9 C -0.0096(2) 0.24577(19) 0.5910(3) 0.0510(9) Uani 1 1 d .
H9A H 0.0049 0.2170 0.5500 0.077 Uiso 1 1 calc R
H9B H -0.0351 0.2921 0.5578 0.077 Uiso 1 1 calc R
H9C H -0.0479 0.2176 0.6020 0.077 Uiso 1 1 calc R
C10 C 0.07139(18) 0.07712(15) 0.6956(2) 0.0298(6) Uani 1 1 d .
C11 C 0.1610(2) 0.1150(2) 0.6470(2) 0.0429(8) Uani 1 1 d .
H11A H 0.1971 0.1451 0.6378 0.051 Uiso 1 1 calc R
C12 C 0.1388(2) 0.0449(2) 0.6153(2) 0.0431(8) Uani 1 1 d .
H12A H 0.1568 0.0166 0.5799 0.052 Uiso 1 1 calc R
C13 C 0.0499(2) -0.05336(19) 0.6268(3) 0.0464(9) Uani 1 1 d .
H13A H 0.0267 -0.0662 0.5569 0.056 Uiso 1 1 calc R
H13B H 0.0054 -0.0555 0.6413 0.056 Uiso 1 1 calc R
C14 C 0.1174(2) -0.1097(2) 0.6923(3) 0.0519(9) Uani 1 1 d .
H14A H 0.0976 -0.1602 0.6690 0.062 Uiso 1 1 calc R
H14B H 0.1663 -0.1011 0.6873 0.062 Uiso 1 1 calc R
C15 C 0.2269(3) -0.1244(2) 0.8741(3) 0.0558(10) Uani 1 1 d .
C16 C 0.2907(3) -0.0715(3) 0.8760(4) 0.0780(13) Uani 1 1 d .
H16A H 0.2858 -0.0713 0.8115 0.117 Uiso 1 1 calc R
H16B H 0.3456 -0.0878 0.9258 0.117 Uiso 1 1 calc R
H16C H 0.2813 -0.0216 0.8917 0.117 Uiso 1 1 calc R
C17 C 0.2294(4) -0.1200(3) 0.9730(3) 0.0870(17) Uani 1 1 d .
H17A H 0.1850 -0.1497 0.9690 0.131 Uiso 1 1 calc R
H17B H 0.2229 -0.0687 0.9867 0.131 Uiso 1 1 calc R
H17C H 0.2818 -0.1389 1.0257 0.131 Uiso 1 1 calc R
C18 C 0.2422(3) -0.2042(2) 0.8552(3) 0.0799(14) Uani 1 1 d .
H18A H 0.2507 -0.2053 0.7995 0.120 Uiso 1 1 calc R
H18B H 0.1948 -0.2346 0.8404 0.120 Uiso 1 1 calc R
H18C H 0.2908 -0.2234 0.9137 0.120 Uiso 1 1 calc R
O1 O 0.0339(6) -0.4197(14) 0.6023(17) 0.61(2) Uani 1 1 d .
O2 O 0.0000 -0.359(2) 0.7500 0.63(3) Uani 1 2 d S
O3 O 0.0000 -0.1953(7) 0.7500 0.470(15) Uani 1 2 d S
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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
C10 Ni C10 178.65(17) 2_556 .
C10 Ni Cl 89.99(8) 2_556 .
C10 Ni Cl 90.06(8) . .
C10 Ni Cl 90.06(8) 2_556 2_556
C10 Ni Cl 89.99(8) . 2_556
Cl Ni Cl 175.57(5) . 2_556
C10 N1 C11 111.0(3) . .
C10 N1 C6 127.1(2) . .
C11 N1 C6 121.9(3) . .
C10 N2 C12 110.5(3) . .
C10 N2 C13 126.7(3) . .
C12 N2 C13 122.7(3) . .
C14 N3 C15 116.8(3) . .
C6 C1 C2 118.2(3) . .
C6 C1 C7 122.1(3) . .
C2 C1 C7 119.7(3) . .
C3 C2 C1 121.5(3) . .
C4 C3 C2 118.1(3) . .
C4 C3 C8 120.6(3) . .
C2 C3 C8 121.3(3) . .
C5 C4 C3 122.7(3) . .
C4 C5 C6 117.6(3) . .
C4 C5 C9 120.9(3) . .
C6 C5 C9 121.6(3) . .
C1 C6 C5 121.9(3) . .
C1 C6 N1 118.3(3) . .
C5 C6 N1 119.6(3) . .
N1 C10 N2 104.3(2) . .
N1 C10 Ni 127.7(2) . .
N2 C10 Ni 128.0(2) . .
C12 C11 N1 106.6(3) . .
C11 C12 N2 107.6(3) . .
N2 C13 C14 110.4(3) . .
N3 C14 C13 110.6(3) . .
C18 C15 C16 111.3(4) . .
C18 C15 N3 108.8(4) . .
C16 C15 N3 111.9(3) . .
C18 C15 C17 109.7(3) . .
C16 C15 C17 109.7(4) . .
N3 C15 C17 105.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni C10 1.916(3) 2_556
Ni C10 1.916(3) .
Ni Cl 2.1923(7) .
Ni Cl 2.1923(7) 2_556
N1 C10 1.359(4) .
N1 C11 1.393(4) .
N1 C6 1.441(4) .
N2 C10 1.359(4) .
N2 C12 1.390(4) .
N2 C13 1.440(4) .
N3 C14 1.446(4) .
N3 C15 1.504(5) .
C1 C6 1.392(4) .
C1 C2 1.395(4) .
C1 C7 1.506(4) .
C2 C3 1.387(5) .
C3 C4 1.389(5) .
C3 C8 1.501(4) .
C4 C5 1.383(4) .
C5 C6 1.394(4) .
C5 C9 1.504(4) .
C11 C12 1.326(5) .
C13 C14 1.521(5) .
C15 C18 1.507(5) .
C15 C16 1.511(6) .
C15 C17 1.518(5) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C6 C1 C2 C3 -1.0(4) .
C7 C1 C2 C3 177.7(3) .
C1 C2 C3 C4 -0.6(4) .
C1 C2 C3 C8 -179.7(3) .
C2 C3 C4 C5 1.2(5) .
C8 C3 C4 C5 -179.6(3) .
C3 C4 C5 C6 -0.3(5) .
C3 C4 C5 C9 -178.7(3) .
C2 C1 C6 C5 2.0(4) .
C7 C1 C6 C5 -176.6(3) .
C2 C1 C6 N1 176.7(2) .
C7 C1 C6 N1 -1.9(4) .
C4 C5 C6 C1 -1.4(4) .
C9 C5 C6 C1 177.1(3) .
C4 C5 C6 N1 -176.0(3) .
C9 C5 C6 N1 2.4(4) .
C10 N1 C6 C1 105.5(3) .
C11 N1 C6 C1 -75.3(3) .
C10 N1 C6 C5 -79.6(4) .
C11 N1 C6 C5 99.6(3) .
C11 N1 C10 N2 0.2(3) .
C6 N1 C10 N2 179.5(3) .
C11 N1 C10 Ni -178.3(2) .
C6 N1 C10 Ni 1.0(4) .
C12 N2 C10 N1 0.0(3) .
C13 N2 C10 N1 176.6(3) .
C12 N2 C10 Ni 178.4(2) .
C13 N2 C10 Ni -4.9(4) .
C10 Ni C10 N1 19.3(3) 2_556
Cl Ni C10 N1 -73.0(2) .
Cl Ni C10 N1 111.5(2) 2_556
C10 Ni C10 N2 -158.9(2) 2_556
Cl Ni C10 N2 108.9(2) .
Cl Ni C10 N2 -66.7(2) 2_556
C10 N1 C11 C12 -0.4(3) .
C6 N1 C11 C12 -179.7(3) .
N1 C11 C12 N2 0.3(4) .
C10 N2 C12 C11 -0.2(4) .
C13 N2 C12 C11 -177.0(3) .
C10 N2 C13 C14 -106.4(3) .
C12 N2 C13 C14 69.9(4) .
C15 N3 C14 C13 -151.9(3) .
N2 C13 C14 N3 72.3(4) .
C14 N3 C15 C18 -56.1(4) .
C14 N3 C15 C16 67.2(4) .
C14 N3 C15 C17 -173.7(3) .
