#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:01:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178734 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/45/4084559.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_4084559
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         'C30 H44 N4 Ni O4, 2(F6 P), C4 H10 O '
_chemical_formula_sum            'C34 H54 F12 N4 Ni O5 P2'
_chemical_formula_weight         947.46
_chemical_name_common            (IMesOEt)2Ni(H2O)2(PF6)2(Et2O)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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                 104.354(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.0223(7)
_cell_length_b                   16.8551(6)
_cell_length_c                   15.9793(4)
_cell_measurement_reflns_used    12225
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     4441.5(3)
_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)'
_diffrn_ambient_temperature      233(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0599
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20268
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.35
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  0.8057
_exptl_absorpt_correction_T_min  0.6921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1968
_exptl_crystal_recrystallization_method 'Acetone - Ether'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.156
_refine_diff_density_min         -1.168
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0956
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1733P)²+19.7976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2756
_refine_ls_wR_factor_ref         0.2951
_reflns_number_gt                3146
_reflns_number_total             4368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5008506_si_002.cif
_cod_data_source_block           compound_27-Et2O
_cod_depositor_comments
'Adding full bibliography for 4084545--4084559.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4084559
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9193(3) 0.2188(3) 0.2221(3) 0.0367(11) Uani 1 1 d . . .
C2 C 0.8336(4) 0.1254(4) 0.1526(4) 0.0516(15) Uani 1 1 d . . .
H2 H 0.8087 0.0887 0.1110 0.062 Uiso 1 1 calc R . .
C3 C 0.8108(4) 0.1443(4) 0.2237(4) 0.0506(14) Uani 1 1 d . . .
H3 H 0.7677 0.1224 0.2419 0.061 Uiso 1 1 calc R . .
C4 C 0.8519(4) 0.2454(4) 0.3417(4) 0.0487(14) Uani 1 1 d . . .
H4A H 0.8977 0.2805 0.3626 0.058 Uiso 1 1 calc R . .
H4B H 0.8504 0.2079 0.3873 0.058 Uiso 1 1 calc R . .
C5 C 0.7748(4) 0.2933(4) 0.3210(4) 0.0547(16) Uani 1 1 d . . .
H5A H 0.7284 0.2583 0.3028 0.066 Uiso 1 1 calc R . .
H5B H 0.7694 0.3218 0.3720 0.066 Uiso 1 1 calc R . .
C6 C 0.7052(5) 0.3926(6) 0.2266(7) 0.097(3) Uani 1 1 d . . .
H6A H 0.6598 0.3572 0.2105 0.146 Uiso 1 1 calc R . .
H6B H 0.7081 0.4247 0.1778 0.146 Uiso 1 1 calc R . .
H6C H 0.6988 0.4261 0.2730 0.146 Uiso 1 1 calc R . .
C8 C 0.9403(3) 0.1742(3) 0.0814(3) 0.0422(12) Uani 1 1 d . . .
C9 C 0.9200(4) 0.2366(4) 0.0219(4) 0.0526(15) Uani 1 1 d . . .
C10 C 0.9598(4) 0.2384(4) -0.0454(4) 0.0582(16) Uani 1 1 d . . .
H10 H 0.9490 0.2800 -0.0849 0.070 Uiso 1 1 calc R . .
C11 C 1.0144(4) 0.1804(5) -0.0547(4) 0.0596(17) Uani 1 1 d . . .
C12 C 1.0305(4) 0.1200(4) 0.0043(4) 0.0534(15) Uani 1 1 d . . .
H12 H 1.0674 0.0811 -0.0017 0.064 Uiso 1 1 calc R . .
C13 C 0.9939(4) 0.1143(4) 0.0730(3) 0.0461(13) Uani 1 1 d . . .
C14 C 0.8583(5) 0.2993(4) 0.0265(5) 0.0669(19) Uani 1 1 d . . .
H14A H 0.8207 0.2788 0.0570 0.100 Uiso 1 1 calc R . .
H14B H 0.8296 0.3143 -0.0309 0.100 Uiso 1 1 calc R . .
H14C H 0.8853 0.3449 0.0565 0.100 Uiso 1 1 calc R . .
C15 C 1.0578(6) 0.1880(6) -0.1264(5) 0.087(3) Uani 1 1 d . . .
H15A H 1.0211 0.2092 -0.1771 0.130 Uiso 1 1 calc R . .
H15B H 1.0762 0.1367 -0.1393 0.130 Uiso 1 1 calc R . .
H15C H 1.1034 0.2229 -0.1083 0.130 Uiso 1 1 calc R . .
C16 C 1.0136(5) 0.0469(4) 0.1372(4) 0.0583(17) Uani 1 1 d . . .
H16A H 1.0412 0.0673 0.1928 0.087 Uiso 1 1 calc R . .
H16B H 1.0477 0.0091 0.1183 0.087 Uiso 1 1 calc R . .
H16C H 0.9642 0.0214 0.1413 0.087 Uiso 1 1 calc R . .
C18 C 0.9740(6) 0.4312(5) 0.8129(6) 0.080(2) Uani 1 1 d . . .
H18A H 1.0185 0.3981 0.8436 0.096 Uiso 1 1 calc R . .
H18B H 0.9300 0.3968 0.7840 0.096 Uiso 1 1 calc R . .
C17 C 0.9470(8) 0.4821(7) 0.8741(7) 0.122(4) Uani 1 1 d . . .
H17A H 0.8893 0.4894 0.8553 0.182 Uiso 1 1 calc R . .
H17B H 0.9735 0.5327 0.8772 0.182 Uiso 1 1 calc R . .
H17C H 0.9603 0.4578 0.9302 0.182 Uiso 1 1 calc R . .
N1 N 0.8628(3) 0.2023(3) 0.2656(3) 0.0412(10) Uani 1 1 d . . .
N2 N 0.9018(3) 0.1711(3) 0.1521(3) 0.0412(10) Uani 1 1 d . . .
O1 O 0.7773(3) 0.3480(3) 0.2536(3) 0.0621(12) Uani 1 1 d . . .
O2 O 1.0796(3) 0.3787(3) 0.2788(4) 0.0576(12) Uani 1 1 d D . .
O3 O 1.0000 0.4784(4) 0.7500 0.0625(17) Uani 1 2 d S . .
Ni1 Ni 1.0000 0.29704(5) 0.2500 0.0365(4) Uani 1 2 d S . .
P1 P 0.7294(8) 0.9494(9) 0.9492(9) 0.0706(12) Uani 0.288(5) 1 d PD A 1
F2A F 0.7895(12) 0.9257(12) 0.8918(14) 0.1270(14) Uani 0.288(5) 1 d PD A 1
F3A F 0.6664(11) 0.9744(12) 0.9989(12) 0.1270(14) Uani 0.288(5) 1 d PD A 1
F4A F 0.7905(14) 0.9267(16) 1.0381(14) 0.1270(14) Uani 0.288(5) 1 d PD A 1
F5A F 0.7720(11) 1.0300(11) 0.9652(12) 0.1270(14) Uani 0.288(5) 1 d PD A 1
F6A F 0.6881(12) 0.8665(11) 0.9295(14) 0.1270(14) Uani 0.288(5) 1 d PD A 1
F1A F 0.6717(11) 0.9819(12) 0.8626(11) 0.1270(14) Uani 0.288(5) 1 d PD A 1
P2 P 0.7160(3) 0.9336(3) 0.9508(4) 0.0706(12) Uani 0.712(5) 1 d PD A 2
F1B F 0.7511(6) 0.9660(6) 1.0427(5) 0.1270(14) Uani 0.712(5) 1 d PD A 2
F2B F 0.6815(5) 0.8922(5) 0.8579(5) 0.1270(14) Uani 0.712(5) 1 d PD A 2
F3B F 0.7653(5) 0.8526(5) 0.9803(5) 0.1270(14) Uani 0.712(5) 1 d PD A 2
F4B F 0.7935(6) 0.9608(6) 0.9171(6) 0.1270(14) Uani 0.712(5) 1 d PD A 2
F5B F 0.6641(6) 1.0082(5) 0.9153(6) 0.1270(14) Uani 0.712(5) 1 d PD A 2
F6B F 0.6418(5) 0.8975(6) 0.9786(6) 0.1270(14) Uani 0.712(5) 1 d PD A 2
H2X H 1.066(4) 0.423(3) 0.290(4) 0.06(2) Uiso 1 1 d D . .
H2Y H 1.126(4) 0.371(6) 0.276(6) 0.10(3) Uiso 1 1 d 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
N2 C1 N1 105.3(5) . .
N2 C1 Ni1 127.9(4) . .
N1 C1 Ni1 126.6(4) . .
C3 C2 N2 107.0(5) . .
C3 C2 H2 126.5 . .
N2 C2 H2 126.5 . .
C2 C3 N1 107.4(5) . .
C2 C3 H3 126.3 . .
N1 C3 H3 126.3 . .
N1 C4 C5 111.5(5) . .
N1 C4 H4A 109.3 . .
C5 C4 H4A 109.3 . .
N1 C4 H4B 109.3 . .
C5 C4 H4B 109.3 . .
H4A C4 H4B 108.0 . .
O1 C5 C4 109.0(5) . .
O1 C5 H5A 109.9 . .
C4 C5 H5A 109.9 . .
O1 C5 H5B 109.9 . .
C4 C5 H5B 109.9 . .
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 . .
C13 C8 C9 122.5(5) . .
C13 C8 N2 119.1(5) . .
C9 C8 N2 118.4(5) . .
C8 C9 C10 116.8(6) . .
C8 C9 C14 123.5(6) . .
C10 C9 C14 119.8(6) . .
C11 C10 C9 122.1(6) . .
C11 C10 H10 118.9 . .
C9 C10 H10 118.9 . .
C12 C11 C10 118.4(6) . .
C12 C11 C15 122.2(7) . .
C10 C11 C15 119.3(7) . .
C11 C12 C13 122.8(6) . .
C11 C12 H12 118.6 . .
C13 C12 H12 118.6 . .
C8 C13 C12 117.3(6) . .
C8 C13 C16 121.3(5) . .
C12 C13 C16 121.3(6) . .
C9 C14 H14A 109.5 . .
C9 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C9 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C11 C15 H15A 109.5 . .
C11 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C11 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
O3 C18 C17 110.3(7) . .
O3 C18 H18A 109.6 . .
C17 C18 H18A 109.6 . .
O3 C18 H18B 109.6 . .
C17 C18 H18B 109.6 . .
H18A C18 H18B 108.1 . .
C18 C17 H17A 109.5 . .
C18 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C18 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C1 N1 C3 110.5(5) . .
C1 N1 C4 125.3(5) . .
C3 N1 C4 123.8(5) . .
C1 N2 C2 109.7(5) . .
C1 N2 C8 125.3(5) . .
C2 N2 C8 124.4(5) . .
C6 O1 C5 112.9(5) . .
Ni1 O2 H2X 120(5) . .
Ni1 O2 H2Y 121(7) . .
H2X O2 H2Y 119(9) . .
C18 O3 C18 112.7(9) 2_756 .
C1 Ni1 C1 90.7(3) 2_755 .
C1 Ni1 O2 90.9(2) 2_755 .
C1 Ni1 O2 178.3(2) . .
C1 Ni1 O2 178.3(2) 2_755 2_755
C1 Ni1 O2 90.9(2) . 2_755
O2 Ni1 O2 87.5(3) . 2_755
F5A P1 F3A 91.9(8) . .
F5A P1 F6A 177.3(10) . .
F3A P1 F6A 90.7(8) . .
F5A P1 F1A 90.3(9) . .
F3A P1 F1A 89.8(9) . .
F6A P1 F1A 89.0(9) . .
F5A P1 F2A 88.5(8) . .
F3A P1 F2A 175.8(13) . .
F6A P1 F2A 88.9(8) . .
F1A P1 F2A 86.1(9) . .
F5A P1 F4A 83.5(14) . .
F3A P1 F4A 89.4(14) . .
F6A P1 F4A 97.2(15) . .
F1A P1 F4A 173.7(15) . .
F2A P1 F4A 94.8(14) . .
F1B P2 F5B 96.4(6) . .
F1B P2 F6B 90.9(5) . .
F5B P2 F6B 89.6(6) . .
F1B P2 F4B 93.6(5) . .
F5B P2 F4B 95.0(6) . .
F6B P2 F4B 173.2(7) . .
F1B P2 F3B 88.3(5) . .
F5B P2 F3B 175.1(6) . .
F6B P2 F3B 89.1(5) . .
F4B P2 F3B 85.9(5) . .
F1B P2 F2B 175.0(6) . .
F5B P2 F2B 88.3(5) . .
F6B P2 F2B 87.6(5) . .
F4B P2 F2B 87.5(5) . .
F3B P2 F2B 87.0(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.349(7) .
C1 N1 1.349(7) .
C1 Ni1 1.876(5) .
C2 C3 1.326(9) .
C2 N2 1.395(7) .
C2 H2 0.9300 .
C3 N1 1.376(7) .
C3 H3 0.9300 .
C4 N1 1.467(7) .
C4 C5 1.506(8) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 O1 1.426(7) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 O1 1.411(9) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C8 C13 1.390(8) .
C8 C9 1.402(9) .
C8 N2 1.441(7) .
C9 C10 1.407(9) .
C9 C14 1.504(9) .
C10 C11 1.383(10) .
C10 H10 0.9300 .
C11 C12 1.369(10) .
C11 C15 1.513(10) .
C12 C13 1.392(9) .
C12 H12 0.9300 .
C13 C16 1.513(9) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C18 O3 1.434(8) .
C18 C17 1.460(14) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
O2 Ni1 1.907(4) .
O2 H2X 0.82(5) .
O2 H2Y 0.82(5) .
O3 C18 1.434(8) 2_756
Ni1 C1 1.876(5) 2_755
Ni1 O2 1.907(4) 2_755
P1 F5A 1.530(17) .
P1 F3A 1.543(16) .
P1 F6A 1.561(16) .
P1 F1A 1.583(16) .
P1 F2A 1.585(16) .
P1 F4A 1.586(16) .
P2 F1B 1.542(9) .
P2 F5B 1.560(9) .
P2 F6B 1.563(9) .
P2 F4B 1.609(9) .
P2 F3B 1.612(9) .
P2 F2B 1.613(9) .
