#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:01:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178734 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/45/4084554.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_4084554
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         'C46 H56 Br2 N4 Ni S2'
_chemical_formula_sum            'C46 H56 Br2 N4 Ni S2'
_chemical_formula_weight         947.60
_chemical_name_common            '[NiBr2{ImDiPP(EtSPh)}2]'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 106.614(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.5158(2)
_cell_length_b                   13.6489(4)
_cell_length_c                   14.3381(4)
_cell_measurement_reflns_used    11510
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2159.55(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19835
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.37
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_T_max  0.5225
_exptl_absorpt_correction_T_min  0.4671
_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    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             980
_exptl_crystal_recrystallization_method 'THF - Pentane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0297
_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)+(0.0273P)²+0.9018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0661
_reflns_number_gt                3532
_reflns_number_total             4232
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5008506_si_002.cif
_cod_data_source_block           compound_19
_cod_depositor_comments
'Adding full bibliography for 4084545--4084559.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4084554
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 0.5000 0.02230(10) Uani 1 2 d S
C1 C 0.96202(17) 0.04501(14) 0.36828(14) 0.0211(4) Uani 1 1 d .
C2 C 0.88227(18) 0.04962(16) 0.20451(15) 0.0264(5) Uani 1 1 d .
H2 H 0.8402 0.0307 0.1416 0.032 Uiso 1 1 calc R
C3 C 0.94340(18) 0.13345(16) 0.23062(15) 0.0256(5) Uani 1 1 d .
H3 H 0.9514 0.1840 0.1895 0.031 Uiso 1 1 calc R
C4 C 0.8383(2) -0.09891(15) 0.29450(17) 0.0311(5) Uani 1 1 d .
H4A H 0.8898 -0.1353 0.3488 0.037 Uiso 1 1 calc R
H4B H 0.8339 -0.1354 0.2355 0.037 Uiso 1 1 calc R
C5 C 0.7120(2) -0.09170(17) 0.30709(19) 0.0406(6) Uani 1 1 d .
H5A H 0.7122 -0.0405 0.3541 0.049 Uiso 1 1 calc R
H5B H 0.6936 -0.1530 0.3341 0.049 Uiso 1 1 calc R
C6 C 0.5933(2) 0.06269(19) 0.18407(19) 0.0398(6) Uani 1 1 d .
C7 C 0.5906(2) 0.1253(2) 0.2586(2) 0.0470(7) Uani 1 1 d .
H7 H 0.5907 0.1006 0.3190 0.056 Uiso 1 1 calc R
C8 C 0.5879(3) 0.2251(2) 0.2431(3) 0.0669(9) Uani 1 1 d .
H8 H 0.5871 0.2676 0.2936 0.080 Uiso 1 1 calc R
C9 C 0.5863(3) 0.2623(3) 0.1539(3) 0.0786(12) Uani 1 1 d .
H9 H 0.5836 0.3297 0.1439 0.094 Uiso 1 1 calc R
C10 C 0.5886(3) 0.2006(3) 0.0802(3) 0.0756(11) Uani 1 1 d .
H10 H 0.5878 0.2259 0.0198 0.091 Uiso 1 1 calc R
C11 C 0.5922(2) 0.1015(2) 0.0942(2) 0.0579(8) Uani 1 1 d .
H11 H 0.5938 0.0598 0.0433 0.070 Uiso 1 1 calc R
C12 C 1.07098(18) 0.20457(14) 0.38869(14) 0.0226(4) Uani 1 1 d .
C13 C 1.19654(18) 0.19053(15) 0.41036(15) 0.0258(5) Uani 1 1 d .
C14 C 1.2702(2) 0.26093(17) 0.46922(17) 0.0338(5) Uani 1 1 d .
H14 H 1.3539 0.2540 0.4856 0.041 Uiso 1 1 calc R
C15 C 1.2214(2) 0.34056(17) 0.50360(17) 0.0375(6) Uani 1 1 d .
H15 H 1.2723 0.3854 0.5445 0.045 Uiso 1 1 calc R
C16 C 1.0976(2) 0.35415(16) 0.47774(16) 0.0326(5) Uani 1 1 d .
H16 H 1.0662 0.4090 0.5004 0.039 Uiso 1 1 calc R
C17 C 1.01855(19) 0.28725(15) 0.41820(15) 0.0249(4) Uani 1 1 d .
C18 C 0.88472(19) 0.31047(15) 0.38047(15) 0.0270(5) Uani 1 1 d .
H18 H 0.8414 0.2493 0.3575 0.032 Uiso 1 1 calc R
C19 C 0.8308(2) 0.35558(17) 0.45626(18) 0.0383(6) Uani 1 1 d .
H19A H 0.8451 0.3128 0.5115 0.057 Uiso 1 1 calc R
H19B H 0.7451 0.3645 0.4284 0.057 Uiso 1 1 calc R
H19C H 0.8682 0.4179 0.4765 0.057 Uiso 1 1 calc R
C20 C 0.8638(2) 0.38046(17) 0.29345(18) 0.0397(6) Uani 1 1 d .
H20A H 0.9076 0.4402 0.3139 0.060 Uiso 1 1 calc R
H20B H 0.7789 0.3946 0.2686 0.060 Uiso 1 1 calc R
H20C H 0.8918 0.3503 0.2433 0.060 Uiso 1 1 calc R
C21 C 1.25093(19) 0.10793(15) 0.36576(16) 0.0292(5) Uani 1 1 d .
H21 H 1.1940 0.0529 0.3538 0.035 Uiso 1 1 calc R
C22 C 1.3730(2) 0.07136(19) 0.43157(19) 0.0421(6) Uani 1 1 d .
H22A H 1.4332 0.1214 0.4373 0.063 Uiso 1 1 calc R
H22B H 1.3970 0.0136 0.4037 0.063 Uiso 1 1 calc R
H22C H 1.3651 0.0563 0.4949 0.063 Uiso 1 1 calc R
C23 C 1.2663(2) 0.14027(18) 0.26767(17) 0.0386(6) Uani 1 1 d .
H23A H 1.1891 0.1596 0.2251 0.058 Uiso 1 1 calc R
H23B H 1.2980 0.0868 0.2389 0.058 Uiso 1 1 calc R
H23C H 1.3214 0.1946 0.2775 0.058 Uiso 1 1 calc R
N1 N 0.89361(15) -0.00358(12) 0.28890(12) 0.0245(4) Uani 1 1 d .
N2 N 0.99267(14) 0.13023(12) 0.33130(12) 0.0209(4) Uani 1 1 d .
S1 S 0.59161(6) -0.06594(5) 0.19626(6) 0.0595(2) Uani 1 1 d .
Br1 Br 1.15134(2) -0.101162(16) 0.477210(16) 0.03348(8) 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 180.0 3_756 .
C1 Ni1 Br1 91.20(6) 3_756 3_756
C1 Ni1 Br1 88.80(6) . 3_756
C1 Ni1 Br1 88.80(6) 3_756 .
C1 Ni1 Br1 91.20(6) . .
Br1 Ni1 Br1 180.000(11) 3_756 .
N1 C1 N2 104.06(16) . .
N1 C1 Ni1 125.77(14) . .
N2 C1 Ni1 130.16(14) . .
C3 C2 N1 107.03(18) . .
C3 C2 H2 126.5 . .
N1 C2 H2 126.5 . .
C2 C3 N2 106.77(18) . .
C2 C3 H3 126.6 . .
N2 C3 H3 126.6 . .
N1 C4 C5 113.34(17) . .
N1 C4 H4A 108.9 . .
C5 C4 H4A 108.9 . .
N1 C4 H4B 108.9 . .
C5 C4 H4B 108.9 . .
H4A C4 H4B 107.7 . .
C4 C5 S1 115.15(18) . .
C4 C5 H5A 108.5 . .
S1 C5 H5A 108.5 . .
C4 C5 H5B 108.5 . .
S1 C5 H5B 108.5 . .
H5A C5 H5B 107.5 . .
C7 C6 C11 119.1(3) . .
C7 C6 S1 122.6(2) . .
C11 C6 S1 118.3(2) . .
C6 C7 C8 119.6(3) . .
C6 C7 H7 120.2 . .
C8 C7 H7 120.2 . .
C9 C8 C7 120.7(3) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C10 C9 C8 119.9(3) . .
C10 C9 H9 120.1 . .
C8 C9 H9 120.1 . .
C9 C10 C11 120.4(3) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
C10 C11 C6 120.4(3) . .
C10 C11 H11 119.8 . .
C6 C11 H11 119.8 . .
C17 C12 C13 123.30(18) . .
C17 C12 N2 118.95(17) . .
C13 C12 N2 117.74(17) . .
C14 C13 C12 116.73(19) . .
C14 C13 C21 120.95(19) . .
C12 C13 C21 122.13(18) . .
C15 C14 C13 121.4(2) . .
C15 C14 H14 119.3 . .
C13 C14 H14 119.3 . .
C14 C15 C16 120.4(2) . .
C14 C15 H15 119.8 . .
C16 C15 H15 119.8 . .
C15 C16 C17 121.3(2) . .
C15 C16 H16 119.3 . .
C17 C16 H16 119.3 . .
C16 C17 C12 116.72(19) . .
C16 C17 C18 120.09(19) . .
C12 C17 C18 122.90(18) . .
C17 C18 C19 114.19(18) . .
C17 C18 C20 109.15(17) . .
C19 C18 C20 109.04(18) . .
C17 C18 H18 108.1 . .
C19 C18 H18 108.1 . .
C20 C18 H18 108.1 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C13 C21 C23 110.05(17) . .
C13 C21 C22 113.48(19) . .
C23 C21 C22 109.39(19) . .
C13 C21 H21 107.9 . .
C23 C21 H21 107.9 . .
C22 C21 H21 107.9 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21 C23 H23A 109.5 . .
C21 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C21 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C1 N1 C2 111.31(16) . .
C1 N1 C4 123.13(17) . .
C2 N1 C4 125.54(17) . .
C1 N2 C3 110.82(16) . .
C1 N2 C12 124.35(16) . .
C3 N2 C12 124.76(16) . .
C6 S1 C5 104.56(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 C1 1.914(2) 3_756
Ni1 C1 1.914(2) .
Ni1 Br1 2.3186(2) 3_756
Ni1 Br1 2.3186(2) .
C1 N1 1.358(3) .
C1 N2 1.366(2) .
C2 C3 1.339(3) .
C2 N1 1.385(3) .
C2 H2 0.9300 .
C3 N2 1.392(3) .
C3 H3 0.9300 .
C4 N1 1.461(2) .
C4 C5 1.519(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 S1 1.820(3) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.376(4) .
C6 C11 1.389(4) .
C6 S1 1.765(3) .
C7 C8 1.379(4) .
C7 H7 0.9300 .
C8 C9 1.371(5) .
C8 H8 0.9300 .
C9 C10 1.358(5) .
C9 H9 0.9300 .
C10 C11 1.367(5) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C17 1.401(3) .
C12 C13 1.403(3) .
C12 N2 1.448(2) .
C13 C14 1.395(3) .
C13 C21 1.517(3) .
C14 C15 1.377(3) .
C14 H14 0.9300 .
C15 C16 1.379(3) .
C15 H15 0.9300 .
C16 C17 1.395(3) .
C16 H16 0.9300 .
C17 C18 1.514(3) .
C18 C19 1.527(3) .
C18 C20 1.535(3) .
C18 H18 0.9800 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 C23 1.532(3) .
C21 C22 1.535(3) .
C21 H21 0.9800 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 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 -154(100) 3_756
Br1 Ni1 C1 N1 -100.08(16) 3_756
Br1 Ni1 C1 N1 79.92(16) .
C1 Ni1 C1 N2 25(100) 3_756
Br1 Ni1 C1 N2 78.62(17) 3_756
Br1 Ni1 C1 N2 -101.38(17) .
N1 C2 C3 N2 0.5(2) .
N1 C4 C5 S1 79.4(2) .
C11 C6 C7 C8 -0.5(4) .
S1 C6 C7 C8 -177.7(2) .
C6 C7 C8 C9 0.8(4) .
C7 C8 C9 C10 -0.6(5) .
C8 C9 C10 C11 0.2(5) .
C9 C10 C11 C6 0.0(4) .
C7 C6 C11 C10 0.1(4) .
S1 C6 C11 C10 177.4(2) .
C17 C12 C13 C14 3.9(3) .
N2 C12 C13 C14 -177.32(18) .
C17 C12 C13 C21 -171.16(19) .
N2 C12 C13 C21 7.6(3) .
C12 C13 C14 C15 -0.5(3) .
C21 C13 C14 C15 174.7(2) .
C13 C14 C15 C16 -2.1(3) .
C14 C15 C16 C17 1.4(3) .
C15 C16 C17 C12 1.9(3) .
C15 C16 C17 C18 -172.1(2) .
C13 C12 C17 C16 -4.6(3) .
N2 C12 C17 C16 176.65(18) .
C13 C12 C17 C18 169.20(18) .
N2 C12 C17 C18 -9.6(3) .
C16 C17 C18 C19 -43.0(3) .
C12 C17 C18 C19 143.4(2) .
C16 C17 C18 C20 79.3(2) .
C12 C17 C18 C20 -94.2(2) .
C14 C13 C21 C23 -87.9(2) .
C12 C13 C21 C23 86.9(2) .
C14 C13 C21 C22 35.0(3) .
C12 C13 C21 C22 -150.1(2) .
N2 C1 N1 C2 0.3(2) .
Ni1 C1 N1 C2 179.25(14) .
N2 C1 N1 C4 -178.61(17) .
Ni1 C1 N1 C4 0.4(3) .
C3 C2 N1 C1 -0.5(2) .
C3 C2 N1 C4 178.35(19) .
C5 C4 N1 C1 89.9(2) .
C5 C4 N1 C2 -88.9(3) .
N1 C1 N2 C3 0.0(2) .
Ni1 C1 N2 C3 -178.87(15) .
N1 C1 N2 C12 -176.98(17) .
Ni1 C1 N2 C12 4.1(3) .
C2 C3 N2 C1 -0.3(2) .
C2 C3 N2 C12 176.66(18) .
C17 C12 N2 C1 -99.1(2) .
C13 C12 N2 C1 82.1(2) .
C17 C12 N2 C3 84.3(2) .
C13 C12 N2 C3 -94.5(2) .
C7 C6 S1 C5 -51.1(2) .
C11 C6 S1 C5 131.7(2) .
C4 C5 S1 C6 -83.95(18) .
