#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:32:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179145 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/06/4310667.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_4310667
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 H20 Cl2 N Ni O P'
_chemical_formula_sum            'C20 H20 Cl2 N Ni O P'
_chemical_formula_weight         450.95
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_date             10-05-02
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.291(5)
_cell_angle_beta                 108.428(5)
_cell_angle_gamma                98.439(5)
_cell_formula_units_Z            2
_cell_length_a                   9.151(5)
_cell_length_b                   10.262(5)
_cell_length_c                   11.874(5)
_cell_measurement_reflns_used    5631
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1020.4(9)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0846
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4646
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    1.300
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0357
_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)+(0.0505P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                3774
_reflns_number_total             4645
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic035132isi20030930_073504.cif
_cod_data_source_block           pbr35
_cod_database_code               4310667
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.48619(4) 0.55960(3) 0.22061(3) 0.01773(12) Uani 1 1 d . . .
P P 0.54632(8) 0.74979(6) 0.34500(6) 0.01702(16) Uani 1 1 d . . .
Cl1 Cl 0.39865(8) 0.35696(6) 0.09515(6) 0.02526(17) Uani 1 1 d . . .
Cl2 Cl 0.71649(9) 0.52082(8) 0.30790(7) 0.0345(2) Uani 1 1 d . . .
N N 0.2981(3) 0.6173(2) 0.1360(2) 0.0187(5) Uani 1 1 d . . .
O1 O 0.3956(2) 0.77425(18) 0.38140(17) 0.0214(4) Uani 1 1 d . . .
C1 C 0.5904(3) 0.8859(3) 0.2736(2) 0.0193(5) Uani 1 1 d . . .
C16 C 0.1956(3) 0.6637(3) 0.1851(2) 0.0209(5) Uani 1 1 d . . .
C19 C 0.1370(4) 0.6379(3) -0.0598(3) 0.0284(6) Uani 1 1 d . . .
H19 H 0.1208 0.6313 -0.1420 0.034 Uiso 1 1 calc . . .
C12 C 0.8524(3) 0.8456(3) 0.5088(3) 0.0261(6) Uani 1 1 d . . .
H12 H 0.8795 0.8585 0.4415 0.031 Uiso 1 1 calc . . .
C4 C 0.6446(4) 1.0886(3) 0.1547(3) 0.0320(7) Uani 1 1 d . . .
H4 H 0.6614 1.1565 0.1141 0.038 Uiso 1 1 calc . . .
C6 C 0.5739(4) 1.0155(3) 0.3160(3) 0.0276(6) Uani 1 1 d . . .
H6 H 0.5451 1.0344 0.3843 0.033 Uiso 1 1 calc . . .
C7 C 0.6973(3) 0.7911(2) 0.4938(2) 0.0187(5) Uani 1 1 d . . .
C2 C 0.6361(3) 0.8590(3) 0.1726(2) 0.0254(6) Uani 1 1 d . . .
H2 H 0.6482 0.7726 0.1447 0.030 Uiso 1 1 calc . . .
C8 C 0.6593(3) 0.7704(3) 0.5951(3) 0.0256(6) Uani 1 1 d . . .
H8 H 0.5566 0.7311 0.5855 0.031 Uiso 1 1 calc . . .
C14 C 0.1325(4) 0.7570(4) 0.3720(3) 0.0356(7) Uani 1 1 d . . .
H14A H 0.1318 0.8414 0.3471 0.053 Uiso 1 1 calc . . .
H14B H 0.1710 0.7737 0.4593 0.053 Uiso 1 1 calc . . .
H14C H 0.0274 0.7030 0.3406 0.053 Uiso 1 1 calc . . .
C3 C 0.6637(4) 0.9607(3) 0.1135(3) 0.0318(7) Uani 1 1 d . . .
H3 H 0.6950 0.9430 0.0463 0.038 Uiso 1 1 calc . . .
C5 C 0.6009(4) 1.1164(3) 0.2556(3) 0.0336(7) Uani 1 1 d . . .
H5 H 0.5895 1.2031 0.2832 0.040 Uiso 1 1 calc . . .
C13 C 0.2392(3) 0.6825(3) 0.3231(2) 0.0224(6) Uani 1 1 d . . .
C20 C 0.2696(3) 0.6067(3) 0.0152(3) 0.0243(6) Uani 1 1 d . . .
H20 H 0.3419 0.5775 -0.0178 0.029 Uiso 1 1 calc . . .
C15 C 0.2438(4) 0.5490(3) 0.3627(3) 0.0304(7) Uani 1 1 d . . .
H15A H 0.2718 0.5650 0.4495 0.046 Uiso 1 1 calc . . .
H15B H 0.3205 0.5081 0.3391 0.046 Uiso 1 1 calc . . .
H15C H 0.1419 0.4898 0.3245 0.046 Uiso 1 1 calc . . .
C10 C 0.9264(4) 0.8628(3) 0.7238(3) 0.0318(7) Uani 1 1 d . . .
H10 H 1.0032 0.8878 0.8011 0.038 Uiso 1 1 calc . . .
C9 C 0.7738(4) 0.8082(3) 0.7104(3) 0.0313(7) Uani 1 1 d . . .
H9 H 0.7474 0.7966 0.7782 0.038 Uiso 1 1 calc . . .
C11 C 0.9670(3) 0.8809(3) 0.6245(3) 0.0306(7) Uani 1 1 d . . .
H11 H 1.0710 0.9166 0.6346 0.037 Uiso 1 1 calc . . .
C18 C 0.0286(4) 0.6790(3) -0.0117(3) 0.0322(7) Uani 1 1 d . . .
H18 H -0.0639 0.6968 -0.0617 0.039 Uiso 1 1 calc . . .
C17 C 0.0589(3) 0.6936(3) 0.1122(3) 0.0289(6) Uani 1 1 d . . .
H17 H -0.0122 0.7233 0.1462 0.035 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
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'
Cl Cl 0.1484 0.1585 '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'
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'
P P 0.1023 0.0942 '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
N Ni P 85.49(7) . . ?
N Ni Cl2 171.04(7) . . ?
P Ni Cl2 90.67(3) . . ?
N Ni Cl1 90.94(7) . . ?
P Ni Cl1 173.62(3) . . ?
Cl2 Ni Cl1 93.59(4) . . ?
O1 P C7 100.30(12) . . ?
O1 P C1 105.78(11) . . ?
C7 P C1 105.17(12) . . ?
O1 P Ni 109.00(7) . . ?
C7 P Ni 124.16(9) . . ?
C1 P Ni 110.72(9) . . ?
C16 N C20 119.2(2) . . ?
C16 N Ni 126.53(18) . . ?
C20 N Ni 114.30(18) . . ?
C13 O1 P 122.79(16) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 P 119.2(2) . . ?
C6 C1 P 120.8(2) . . ?
N C16 C17 120.6(3) . . ?
N C16 C13 116.9(2) . . ?
C17 C16 C13 122.4(2) . . ?
C18 C19 C20 119.2(3) . . ?
C11 C12 C7 119.9(3) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C6 C1 119.5(3) . . ?
C12 C7 C8 119.3(3) . . ?
C12 C7 P 120.3(2) . . ?
C8 C7 P 120.3(2) . . ?
C3 C2 C1 120.1(3) . . ?
C9 C8 C7 120.4(3) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C5 C6 120.2(3) . . ?
O1 C13 C14 103.5(2) . . ?
O1 C13 C15 109.8(2) . . ?
C14 C13 C15 110.5(2) . . ?
O1 C13 C16 107.8(2) . . ?
C14 C13 C16 112.9(2) . . ?
C15 C13 C16 111.9(2) . . ?
N C20 C19 121.9(3) . . ?
C9 C10 C11 120.9(3) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C11 C12 119.9(3) . . ?
C19 C18 C17 119.2(3) . . ?
C16 C17 C18 119.7(3) . . ?
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
Ni N 1.928(2) . ?
Ni P 2.1292(11) . ?
Ni Cl2 2.1615(13) . ?
Ni Cl1 2.2230(11) . ?
P O1 1.611(2) . ?
P C7 1.804(3) . ?
P C1 1.807(3) . ?
N C16 1.355(3) . ?
N C20 1.357(4) . ?
O1 C13 1.477(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.391(4) . ?
C16 C17 1.386(4) . ?
C16 C13 1.531(4) . ?
C19 C18 1.374(4) . ?
C19 C20 1.375(4) . ?
C12 C11 1.391(4) . ?
C12 C7 1.391(4) . ?
C4 C5 1.379(5) . ?
C4 C3 1.380(5) . ?
C6 C5 1.387(4) . ?
C7 C8 1.392(4) . ?
C2 C3 1.385(4) . ?
C8 C9 1.387(4) . ?
C14 C13 1.519(4) . ?
C13 C15 1.520(4) . ?
C10 C9 1.376(5) . ?
C10 C11 1.376(4) . ?
C18 C17 1.387(4) . ?
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
N Ni P O1 47.24(10) . . . . ?
Cl2 Ni P O1 -140.86(8) . . . . ?
Cl1 Ni P O1 -8.9(3) . . . . ?
N Ni P C7 164.78(13) . . . . ?
Cl2 Ni P C7 -23.33(11) . . . . ?
Cl1 Ni P C7 108.6(3) . . . . ?
N Ni P C1 -68.72(12) . . . . ?
Cl2 Ni P C1 103.17(10) . . . . ?
Cl1 Ni P C1 -124.9(3) . . . . ?
P Ni N C16 -52.4(2) . . . . ?
Cl2 Ni N C16 -117.2(4) . . . . ?
Cl1 Ni N C16 122.3(2) . . . . ?
P Ni N C20 128.50(19) . . . . ?
Cl2 Ni N C20 63.7(5) . . . . ?
Cl1 Ni N C20 -56.80(18) . . . . ?
C7 P O1 C13 -138.2(2) . . . . ?
C1 P O1 C13 112.6(2) . . . . ?
Ni P O1 C13 -6.5(2) . . . . ?
O1 P C1 C2 -140.5(2) . . . . ?
C7 P C1 C2 113.9(2) . . . . ?
Ni P C1 C2 -22.5(2) . . . . ?
O1 P C1 C6 37.4(3) . . . . ?
C7 P C1 C6 -68.3(3) . . . . ?
Ni P C1 C6 155.3(2) . . . . ?
C20 N C16 C17 3.3(4) . . . . ?
Ni N C16 C17 -175.7(2) . . . . ?
C20 N C16 C13 -176.0(2) . . . . ?
Ni N C16 C13 4.9(3) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
P C1 C6 C5 -176.7(2) . . . . ?
C11 C12 C7 C8 -1.0(4) . . . . ?
C11 C12 C7 P 178.1(2) . . . . ?
O1 P C7 C12 -149.5(2) . . . . ?
C1 P C7 C12 -39.9(2) . . . . ?
Ni P C7 C12 88.9(2) . . . . ?
O1 P C7 C8 29.6(2) . . . . ?
C1 P C7 C8 139.2(2) . . . . ?
Ni P C7 C8 -92.0(2) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
P C1 C2 C3 177.2(2) . . . . ?
C12 C7 C8 C9 2.3(4) . . . . ?
P C7 C8 C9 -176.9(2) . . . . ?
C5 C4 C3 C2 1.1(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C1 C6 C5 C4 -0.4(5) . . . . ?
P O1 C13 C14 -171.70(19) . . . . ?
P O1 C13 C15 70.4(3) . . . . ?
P O1 C13 C16 -51.8(3) . . . . ?
N C16 C13 O1 56.4(3) . . . . ?
C17 C16 C13 O1 -122.9(3) . . . . ?
N C16 C13 C14 170.1(2) . . . . ?
C17 C16 C13 C14 -9.2(4) . . . . ?
N C16 C13 C15 -64.5(3) . . . . ?
C17 C16 C13 C15 116.2(3) . . . . ?
C16 N C20 C19 -2.0(4) . . . . ?
Ni N C20 C19 177.1(2) . . . . ?
C18 C19 C20 N -1.0(4) . . . . ?
C11 C10 C9 C8 0.2(5) . . . . ?
C7 C8 C9 C10 -1.8(5) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C7 C12 C11 C10 -0.6(5) . . . . ?
C20 C19 C18 C17 2.8(4) . . . . ?
N C16 C17 C18 -1.6(4) . . . . ?
C13 C16 C17 C18 177.7(3) . . . . ?
C19 C18 C17 C16 -1.5(4) . . . . ?
