#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:01:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178734 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/45/4084558.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_4084558
loop_
_publ_author_name
'Hameury, Sophie'
'de Frémont, Pierre'
'Breuil, Pierre-Alain R.'
'Olivier-Bourbigou, Hélène'
'Braunstein, Pierre'
_publ_section_title
;
 Bis(ether-functionalized NHC) Nickel(II)
 Complexes,TranstoCisIsomerization Triggered by Water Coordination, and
 Catalytic Ethylene Oligomerization
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2183
_journal_paper_doi               10.1021/om5008506
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C20 H36 I2 N4 Ni O2'
_chemical_formula_sum            'C20 H36 I2 N4 Ni O2'
_chemical_formula_weight         677.04
_chemical_name_common            '[NiI2{ImnBu(EtOMe)}2]'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                70.248(5)
_cell_angle_beta                 75.665(4)
_cell_angle_gamma                82.213(5)
_cell_formula_units_Z            1
_cell_length_a                   8.2699(7)
_cell_length_b                   8.7576(7)
_cell_length_c                   9.8261(9)
_cell_measurement_reflns_used    7542
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     647.88(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Sir 97'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5828
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.55
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.153
_exptl_absorpt_correction_T_max  0.6772
_exptl_absorpt_correction_T_min  0.5913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             334
_exptl_crystal_recrystallization_method 'THF - Pentane'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0363
_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)+(0.0226P)²+0.7491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0745
_reflns_number_gt                2110
_reflns_number_total             2531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5008506_si_002.cif
_cod_data_source_block           compound_23
_cod_depositor_comments
'Adding full bibliography for 4084545--4084559.cif.'
_cod_database_code               4084558
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
Ni1 Ni 0.5000 1.0000 0.5000 0.02765(19) Uani 1 2 d S
C1 C 0.4184(5) 1.1808(5) 0.5703(5) 0.0295(10) Uani 1 1 d .
C2 C 0.2604(6) 1.3906(5) 0.6284(5) 0.0437(13) Uani 1 1 d .
H2 H 0.1703 1.4649 0.6388 0.052 Uiso 1 1 calc R
C3 C 0.4032(6) 1.3832(5) 0.6680(5) 0.0406(12) Uani 1 1 d .
H3 H 0.4325 1.4513 0.7120 0.049 Uiso 1 1 calc R
C4 C 0.1362(6) 1.2333(6) 0.5109(6) 0.0505(14) Uani 1 1 d .
H4A H 0.0323 1.2845 0.5509 0.061 Uiso 1 1 calc R
H4B H 0.1234 1.1170 0.5460 0.061 Uiso 1 1 calc R
C5 C 0.1648(7) 1.2920(6) 0.3450(7) 0.0526(14) Uani 1 1 d .
H5A H 0.2696 1.2438 0.3031 0.063 Uiso 1 1 calc R
H5B H 0.0754 1.2598 0.3144 0.063 Uiso 1 1 calc R
C6 C 0.2046(11) 1.5246(9) 0.1334(7) 0.099(3) Uani 1 1 d .
H6A H 0.3138 1.4833 0.0953 0.149 Uiso 1 1 calc R
H6B H 0.2008 1.6412 0.0997 0.149 Uiso 1 1 calc R
H6C H 0.1226 1.4883 0.0989 0.149 Uiso 1 1 calc R
C7 C 0.6667(5) 1.1998(5) 0.6634(5) 0.0351(11) Uani 1 1 d .
H7A H 0.7247 1.2932 0.6539 0.042 Uiso 1 1 calc R
H7B H 0.7304 1.1501 0.5906 0.042 Uiso 1 1 calc R
C8 C 0.6602(6) 1.0795(5) 0.8160(5) 0.0360(11) Uani 1 1 d .
H8A H 0.6043 1.1312 0.8896 0.043 Uiso 1 1 calc R
H8B H 0.5959 0.9890 0.8286 0.043 Uiso 1 1 calc R
C9 C 0.8293(5) 1.0185(5) 0.8393(5) 0.0325(10) Uani 1 1 d .
H9A H 0.8899 1.1083 0.8343 0.039 Uiso 1 1 calc R
H9B H 0.8880 0.9762 0.7599 0.039 Uiso 1 1 calc R
C10 C 0.8293(7) 0.8876(7) 0.9849(6) 0.0555(14) Uani 1 1 d .
H10A H 0.7781 0.9306 1.0643 0.083 Uiso 1 1 calc R
H10B H 0.9423 0.8494 0.9920 0.083 Uiso 1 1 calc R
H10C H 0.7675 0.7991 0.9916 0.083 Uiso 1 1 calc R
N1 N 0.2698(5) 1.2663(4) 0.5681(4) 0.0365(9) Uani 1 1 d .
N2 N 0.5018(4) 1.2546(4) 0.6318(4) 0.0315(8) Uani 1 1 d .
O1 O 0.1697(5) 1.4663(4) 0.2923(4) 0.0638(11) Uani 1 1 d .
I1 I 0.32527(4) 0.81539(3) 0.72931(3) 0.03749(12) 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
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
I I -0.4742 1.8119 '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'
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
C1 Ni1 C1 180.000(1) . 2_676
C1 Ni1 I1 90.17(12) . 2_676
C1 Ni1 I1 89.83(12) 2_676 2_676
C1 Ni1 I1 89.83(12) . .
C1 Ni1 I1 90.17(12) 2_676 .
I1 Ni1 I1 180.0 2_676 .
N1 C1 N2 104.3(3) . .
N1 C1 Ni1 129.0(3) . .
N2 C1 Ni1 126.7(3) . .
C3 C2 N1 107.1(4) . .
C3 C2 H2 126.4 . .
N1 C2 H2 126.4 . .
C2 C3 N2 107.2(4) . .
C2 C3 H3 126.4 . .
N2 C3 H3 126.4 . .
N1 C4 C5 114.1(4) . .
N1 C4 H4A 108.7 . .
C5 C4 H4A 108.7 . .
N1 C4 H4B 108.7 . .
C5 C4 H4B 108.7 . .
H4A C4 H4B 107.6 . .
O1 C5 C4 109.3(4) . .
O1 C5 H5A 109.8 . .
C4 C5 H5A 109.8 . .
O1 C5 H5B 109.8 . .
C4 C5 H5B 109.8 . .
H5A C5 H5B 108.3 . .
O1 C6 H6A 109.5 . .
O1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
O1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N2 C7 C8 113.0(4) . .
N2 C7 H7A 109.0 . .
C8 C7 H7A 109.0 . .
N2 C7 H7B 109.0 . .
C8 C7 H7B 109.0 . .
H7A C7 H7B 107.8 . .
C9 C8 C7 111.1(4) . .
C9 C8 H8A 109.4 . .
C7 C8 H8A 109.4 . .
C9 C8 H8B 109.4 . .
C7 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
C8 C9 C10 113.2(4) . .
C8 C9 H9A 108.9 . .
C10 C9 H9A 108.9 . .
C8 C9 H9B 108.9 . .
C10 C9 H9B 108.9 . .
H9A C9 H9B 107.7 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C1 N1 C2 111.0(4) . .
C1 N1 C4 124.9(4) . .
C2 N1 C4 124.1(4) . .
C1 N2 C3 110.4(4) . .
C1 N2 C7 124.5(3) . .
C3 N2 C7 125.0(4) . .
C6 O1 C5 110.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.912(4) .
Ni1 C1 1.912(4) 2_676
Ni1 I1 2.5174(3) 2_676
Ni1 I1 2.5174(3) .
C1 N1 1.351(5) .
C1 N2 1.360(5) .
C2 C3 1.319(7) .
C2 N1 1.389(6) .
C2 H2 0.9300 .
C3 N2 1.393(5) .
C3 H3 0.9300 .
C4 N1 1.458(6) .
C4 C5 1.501(7) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 O1 1.439(6) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 O1 1.435(7) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 N2 1.455(6) .
C7 C8 1.507(6) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.472(6) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.501(7) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
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
C1 Ni1 C1 N1 34(100) 2_676
I1 Ni1 C1 N1 101.7(4) 2_676
I1 Ni1 C1 N1 -78.3(4) .
C1 Ni1 C1 N2 -145(100) 2_676
I1 Ni1 C1 N2 -76.7(3) 2_676
I1 Ni1 C1 N2 103.3(3) .
N1 C2 C3 N2 0.2(5) .
N1 C4 C5 O1 -63.3(5) .
N2 C7 C8 C9 175.9(3) .
C7 C8 C9 C10 -175.1(4) .
N2 C1 N1 C2 -0.5(5) .
Ni1 C1 N1 C2 -179.1(3) .
N2 C1 N1 C4 179.7(4) .
Ni1 C1 N1 C4 1.1(6) .
C3 C2 N1 C1 0.2(5) .
C3 C2 N1 C4 180.0(4) .
C5 C4 N1 C1 -77.5(6) .
C5 C4 N1 C2 102.7(5) .
N1 C1 N2 C3 0.6(5) .
Ni1 C1 N2 C3 179.3(3) .
N1 C1 N2 C7 177.1(4) .
Ni1 C1 N2 C7 -4.3(6) .
C2 C3 N2 C1 -0.5(5) .
C2 C3 N2 C7 -177.0(4) .
C8 C7 N2 C1 -89.7(5) .
C8 C7 N2 C3 86.2(5) .
C4 C5 O1 C6 177.4(5) .
