#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:32:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179145 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/06/4310666.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_4310666
loop_
_publ_author_name
'Fredy Speiser'
'Pierre Braunstein'
'Lucien Saussine'
'Richard Welter'
_publ_contact_author_address
;

Institut Le Bel, rue Blaise Pascal, 67000 STRASBOURG, FRANCE

;
_publ_contact_author_email       braunst@chimie.u-strasbg.fr
_publ_contact_author_fax         0390241322
_publ_contact_author_name
;

Pierre Braunstein

;
_publ_contact_author_phone       0390241308
_publ_section_title
;
 Nickel Complexes with New Bidentate P,N Phosphinitooxazoline and
 -Pyridine Ligands: Application for the Catalytic Oligomerization of
 Ethylene
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1649
_journal_page_last               1658
_journal_paper_doi               10.1021/ic035132i
_journal_volume                  43
_journal_year                    2004
_chemical_formula_moiety         'C20 H24 Cl2 N Ni O2 P'
_chemical_formula_sum            'C20 H24 Cl2 N Ni O2 P'
_chemical_formula_weight         470.98
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_date             10-05-02
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.16(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.999(2)
_cell_length_b                   14.579(2)
_cell_length_c                   16.535(2)
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.018
_cell_volume                     2166.0(6)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'π 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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8331
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    1.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.0026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0369
_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)+(0.0399P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                3521
_reflns_number_total             4950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic035132isi20030930_073434.cif
_cod_data_source_block           st790
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4310666
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
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.80571(6) 0.11070(4) 0.82169(3) 0.02267(16) Uani 1 1 d . . .
Ni Ni 0.85594(3) 0.12876(2) 0.689917(16) 0.02421(11) Uani 1 1 d . . .
N N 1.0671(2) 0.09321(13) 0.71321(10) 0.0244(4) Uani 1 1 d . . .
Cl1 Cl 0.86434(7) 0.27719(4) 0.65977(4) 0.03538(17) Uani 1 1 d . . .
Cl2 Cl 0.71986(7) 0.02444(5) 0.62338(3) 0.03843(18) Uani 1 1 d . . .
O1 O 0.95924(16) 0.10060(11) 0.87723(8) 0.0265(4) Uani 1 1 d . . .
O2 O 1.29312(17) 0.08769(13) 0.77527(9) 0.0383(4) Uani 1 1 d . . .
C1 C 0.7209(2) 0.00257(16) 0.84548(12) 0.0243(5) Uani 1 1 d . . .
C2 C 0.5793(3) -0.00397(18) 0.87413(15) 0.0362(6) Uani 1 1 d . . .
H2 H 0.5260 0.0489 0.8848 0.043 Uiso 1 1 calc . . .
C3 C 0.5175(3) -0.0889(2) 0.88683(16) 0.0444(7) Uani 1 1 d . . .
H3 H 0.4220 -0.0929 0.9054 0.053 Uiso 1 1 calc . . .
C4 C 0.5950(3) -0.16725(19) 0.87239(15) 0.0377(6) Uani 1 1 d . . .
H4 H 0.5528 -0.2242 0.8818 0.045 Uiso 1 1 calc . . .
C5 C 0.7358(3) -0.16199(18) 0.84387(15) 0.0382(6) Uani 1 1 d . . .
H5 H 0.7886 -0.2152 0.8337 0.046 Uiso 1 1 calc . . .
C6 C 0.7979(3) -0.07722(18) 0.83048(14) 0.0338(6) Uani 1 1 d . . .
H6 H 0.8929 -0.0737 0.8111 0.041 Uiso 1 1 calc . . .
C7 C 0.6975(2) 0.19853(16) 0.86757(12) 0.0231(5) Uani 1 1 d . . .
C8 C 0.7139(3) 0.21845(17) 0.94989(13) 0.0278(6) Uani 1 1 d . . .
H8 H 0.7815 0.1854 0.9830 0.033 Uiso 1 1 calc . . .
C9 C 0.6306(3) 0.28687(18) 0.98232(13) 0.0316(6) Uani 1 1 d . . .
H9 H 0.6428 0.3004 1.0372 0.038 Uiso 1 1 calc . . .
C10 C 0.5285(3) 0.33582(18) 0.93357(14) 0.0334(6) Uani 1 1 d . . .
H10 H 0.4720 0.3818 0.9559 0.040 Uiso 1 1 calc . . .
C11 C 0.5108(2) 0.31630(18) 0.85178(14) 0.0304(6) Uani 1 1 d . . .
H11 H 0.4416 0.3486 0.8191 0.037 Uiso 1 1 calc . . .
C12 C 0.5963(3) 0.24850(17) 0.81891(13) 0.0275(5) Uani 1 1 d . . .
H12 H 0.5860 0.2363 0.7637 0.033 Uiso 1 1 calc . . .
C13 C 1.1005(3) 0.14236(17) 0.85888(14) 0.0292(6) Uani 1 1 d . . .
C14 C 1.2066(3) 0.1104(2) 0.92825(15) 0.0469(8) Uani 1 1 d . . .
H14A H 1.2110 0.0446 0.9286 0.070 Uiso 1 1 calc . . .
H14B H 1.1716 0.1316 0.9787 0.070 Uiso 1 1 calc . . .
H14C H 1.3041 0.1348 0.9211 0.070 Uiso 1 1 calc . . .
C15 C 1.0884(3) 0.24569(19) 0.85661(15) 0.0376(6) Uani 1 1 d . . .
H15A H 1.0586 0.2676 0.9080 0.056 Uiso 1 1 calc . . .
H15B H 1.0157 0.2635 0.8149 0.056 Uiso 1 1 calc . . .
H15C H 1.1832 0.2716 0.8455 0.056 Uiso 1 1 calc . . .
C16 C 1.1480(2) 0.10636(16) 0.77871(14) 0.0271(5) Uani 1 1 d . . .
C17 C 1.3181(3) 0.0652(2) 0.69081(15) 0.0418(7) Uani 1 1 d . . .
H17A H 1.3794 0.0108 0.6874 0.050 Uiso 1 1 calc . . .
H17B H 1.3665 0.1157 0.6644 0.050 Uiso 1 1 calc . . .
C18 C 1.1623(3) 0.04853(18) 0.65195(13) 0.0302(6) Uani 1 1 d . . .
C19 C 1.1373(3) 0.0945(2) 0.56980(15) 0.0439(7) Uani 1 1 d . . .
H19A H 1.0375 0.0827 0.5489 0.066 Uiso 1 1 calc . . .
H19B H 1.2065 0.0703 0.5331 0.066 Uiso 1 1 calc . . .
H19C H 1.1520 0.1594 0.5756 0.066 Uiso 1 1 calc . . .
C20 C 1.1222(3) -0.05262(19) 0.64810(16) 0.0424(7) Uani 1 1 d . . .
H20A H 1.0225 -0.0595 0.6252 0.064 Uiso 1 1 calc . . .
H20B H 1.1288 -0.0780 0.7017 0.064 Uiso 1 1 calc . . .
H20C H 1.1900 -0.0842 0.6149 0.064 Uiso 1 1 calc . . .
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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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'
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'
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
_geom_angle_publ_flag
O1 P C7 106.81(9) . . ?
O1 P C1 98.88(9) . . ?
C7 P C1 106.53(11) . . ?
O1 P Ni 110.25(7) . . ?
C7 P Ni 117.63(8) . . ?
C1 P Ni 114.86(7) . . ?
N Ni Cl2 114.54(6) . . ?
N Ni Cl1 104.68(6) . . ?
Cl2 Ni Cl1 125.71(3) . . ?
N Ni P 91.30(7) . . ?
Cl2 Ni P 105.35(3) . . ?
Cl1 Ni P 109.87(3) . . ?
C16 N C18 108.29(18) . . ?
C16 N Ni 127.99(16) . . ?
C18 N Ni 123.66(14) . . ?
C13 O1 P 124.73(13) . . ?
C16 O2 C17 106.72(18) . . ?
C6 C1 C2 118.8(2) . . ?
C6 C1 P 118.27(18) . . ?
C2 C1 P 122.82(19) . . ?
C3 C2 C1 120.0(2) . . ?
C4 C3 C2 120.7(2) . . ?
C3 C4 C5 120.1(3) . . ?
C4 C5 C6 119.6(3) . . ?
C5 C6 C1 120.9(2) . . ?
C12 C7 C8 119.2(2) . . ?
C12 C7 P 118.79(16) . . ?
C8 C7 P 121.98(17) . . ?
C9 C8 C7 120.1(2) . . ?
C8 C9 C10 120.3(2) . . ?
C11 C10 C9 120.0(2) . . ?
C10 C11 C12 119.6(2) . . ?
C11 C12 C7 120.6(2) . . ?
O1 C13 C16 109.30(19) . . ?
O1 C13 C15 111.07(19) . . ?
C16 C13 C15 110.4(2) . . ?
O1 C13 C14 103.5(2) . . ?
C16 C13 C14 111.0(2) . . ?
C15 C13 C14 111.4(2) . . ?
N C16 O2 116.3(2) . . ?
N C16 C13 128.1(2) . . ?
O2 C16 C13 115.6(2) . . ?
O2 C17 C18 104.52(19) . . ?
N C18 C20 107.75(19) . . ?
N C18 C19 110.3(2) . . ?
C20 C18 C19 111.6(2) . . ?
N C18 C17 100.97(18) . . ?
C20 C18 C17 112.5(2) . . ?
C19 C18 C17 113.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P O1 1.6230(16) . ?
P C7 1.801(2) . ?
P C1 1.804(2) . ?
P Ni 2.2649(8) . ?
Ni N 1.9870(18) . ?
Ni Cl2 2.2078(9) . ?
Ni Cl1 2.2229(7) . ?
N C16 1.285(3) . ?
N C18 1.510(3) . ?
O1 C13 1.456(3) . ?
O2 C16 1.338(3) . ?
O2 C17 1.464(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.388(3) . ?
C2 C3 1.378(4) . ?
C3 C4 1.367(4) . ?
C4 C5 1.378(4) . ?
C5 C6 1.379(4) . ?
C7 C12 1.388(3) . ?
C7 C8 1.392(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.383(3) . ?
C13 C16 1.509(3) . ?
C13 C15 1.511(3) . ?
C13 C14 1.525(3) . ?
C17 C18 1.530(3) . ?
C18 C20 1.519(4) . ?
C18 C19 1.520(3) . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P Ni N 12.27(9) . . . . ?
C7 P Ni N 135.03(10) . . . . ?
C1 P Ni N -98.35(10) . . . . ?
O1 P Ni Cl2 128.18(7) . . . . ?
C7 P Ni Cl2 -109.06(9) . . . . ?
C1 P Ni Cl2 17.56(9) . . . . ?
O1 P Ni Cl1 -93.85(7) . . . . ?
C7 P Ni Cl1 28.90(9) . . . . ?
C1 P Ni Cl1 155.53(8) . . . . ?
Cl2 Ni N C16 -138.83(19) . . . . ?
Cl1 Ni N C16 79.7(2) . . . . ?
P Ni N C16 -31.3(2) . . . . ?
Cl2 Ni N C18 44.27(19) . . . . ?
Cl1 Ni N C18 -97.25(18) . . . . ?
P Ni N C18 151.81(17) . . . . ?
C7 P O1 C13 -99.06(18) . . . . ?
C1 P O1 C13 150.57(18) . . . . ?
Ni P O1 C13 29.82(19) . . . . ?
O1 P C1 C6 -57.52(19) . . . . ?
C7 P C1 C6 -168.11(17) . . . . ?
Ni P C1 C6 59.77(19) . . . . ?
O1 P C1 C2 125.86(19) . . . . ?
C7 P C1 C2 15.3(2) . . . . ?
Ni P C1 C2 -116.85(18) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
P C1 C2 C3 176.3(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
P C1 C6 C5 -176.94(19) . . . . ?
O1 P C7 C12 152.96(18) . . . . ?
C1 P C7 C12 -102.1(2) . . . . ?
Ni P C7 C12 28.5(2) . . . . ?
O1 P C7 C8 -26.2(2) . . . . ?
C1 P C7 C8 78.8(2) . . . . ?
Ni P C7 C8 -150.65(17) . . . . ?
C12 C7 C8 C9 0.0(4) . . . . ?
P C7 C8 C9 179.13(19) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C7 1.4(4) . . . . ?
C8 C7 C12 C11 -1.1(4) . . . . ?
P C7 C12 C11 179.77(18) . . . . ?
P O1 C13 C16 -60.7(2) . . . . ?
P O1 C13 C15 61.4(2) . . . . ?
P O1 C13 C14 -178.99(15) . . . . ?
C18 N C16 O2 6.5(3) . . . . ?
Ni N C16 O2 -170.78(16) . . . . ?
C18 N C16 C13 -175.0(2) . . . . ?
Ni N C16 C13 7.7(4) . . . . ?
C17 O2 C16 N 5.7(3) . . . . ?
C17 O2 C16 C13 -173.0(2) . . . . ?
O1 C13 C16 N 42.1(3) . . . . ?
C15 C13 C16 N -80.3(3) . . . . ?
C14 C13 C16 N 155.6(3) . . . . ?
O1 C13 C16 O2 -139.4(2) . . . . ?
C15 C13 C16 O2 98.2(2) . . . . ?
C14 C13 C16 O2 -25.8(3) . . . . ?
C16 O2 C17 C18 -14.9(3) . . . . ?
C16 N C18 C20 103.2(2) . . . . ?
Ni N C18 C20 -79.4(2) . . . . ?
C16 N C18 C19 -134.8(2) . . . . ?
Ni N C18 C19 42.7(3) . . . . ?
C16 N C18 C17 -14.9(3) . . . . ?
Ni N C18 C17 162.53(17) . . . . ?
O2 C17 C18 N 17.4(2) . . . . ?
O2 C17 C18 C20 -97.2(2) . . . . ?
O2 C17 C18 C19 135.3(2) . . . . ?
