#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:37:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178574 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/84/4068495.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_4068495
loop_
_publ_author_name
'Flapper, Jitte'
'Kooijman, Huub'
'Lutz, Martin'
'Spek, Anthony L.'
'van Leeuwen, Piet W. N. M.'
'Elsevier, Cornelis J.'
'Kamer, Paul C. J.'
_publ_section_title
;
 Nickel and Palladium Complexes of Pyridine−Phosphine Ligands as
 Ethene Oligomerization Catalysts
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1180
_journal_paper_doi               10.1021/om800903n
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C23 H18 Cl2 N Ni P'
_chemical_formula_sum            'C23 H18 Cl2 N Ni P'
_chemical_formula_weight         468.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.1048(10)
_cell_length_b                   13.3897(10)
_cell_length_c                   18.552(2)
_cell_measurement_reflns_used    46049
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     4248.9(6)
_computing_cell_refinement       HKL2000
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        HKL2000
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            99443
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0247
_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)+(0.0243P)²+2.8474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0609
_reflns_number_gt                4296
_reflns_number_total             4869
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om800903n_si_001.cif
_cod_data_source_block           s3633b
_cod_database_code               4068495
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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 0.120312(11) 0.404720(13) 0.369489(9) 0.01720(6) Uani 1 1 d .
Cl1 Cl 0.12922(2) 0.46429(3) 0.25829(2) 0.02733(9) Uani 1 1 d .
Cl2 Cl 0.12253(2) 0.47992(3) 0.47555(2) 0.02875(9) Uani 1 1 d .
P1 P 0.19563(2) 0.26660(3) 0.372934(18) 0.01675(8) Uani 1 1 d .
N1 N 0.02487(7) 0.31874(9) 0.36414(6) 0.0188(2) Uani 1 1 d .
C1 C 0.01579(9) 0.23180(10) 0.32731(7) 0.0198(3) Uani 1 1 d .
C2 C -0.05450(9) 0.17969(12) 0.33188(9) 0.0286(3) Uani 1 1 d .
H2 H -0.0597 0.1169 0.3085 0.034 Uiso 1 1 calc R
C3 C -0.11680(10) 0.21874(14) 0.37029(9) 0.0325(4) Uani 1 1 d .
H3 H -0.1650 0.1837 0.3726 0.039 Uiso 1 1 calc R
C4 C -0.10818(9) 0.30923(13) 0.40518(9) 0.0283(3) Uani 1 1 d .
H4 H -0.1506 0.3389 0.4303 0.034 Uiso 1 1 calc R
C5 C -0.03615(9) 0.35498(11) 0.40235(8) 0.0229(3) Uani 1 1 d .
H5 H -0.0290 0.4152 0.4286 0.028 Uiso 1 1 calc R
C6 C 0.07963(9) 0.19146(10) 0.28039(7) 0.0193(3) Uani 1 1 d .
C7 C 0.16056(8) 0.19654(10) 0.29553(7) 0.0185(3) Uani 1 1 d .
C8 C 0.21379(9) 0.14860(11) 0.25000(8) 0.0242(3) Uani 1 1 d .
H8 H 0.2680 0.1505 0.2611 0.029 Uiso 1 1 calc R
C9 C 0.18870(10) 0.09836(11) 0.18883(9) 0.0287(3) Uani 1 1 d .
H9 H 0.2254 0.0653 0.1587 0.034 Uiso 1 1 calc R
C10 C 0.10998(10) 0.09665(11) 0.17192(8) 0.0280(3) Uani 1 1 d .
H10 H 0.0928 0.0650 0.1289 0.034 Uiso 1 1 calc R
C11 C 0.05612(10) 0.14121(11) 0.21772(8) 0.0245(3) Uani 1 1 d .
H11 H 0.0020 0.1376 0.2063 0.029 Uiso 1 1 calc R
C12 C 0.18149(8) 0.18390(11) 0.44934(7) 0.0195(3) Uani 1 1 d .
C13 C 0.16819(11) 0.08225(12) 0.43954(9) 0.0324(4) Uani 1 1 d .
H13 H 0.1687 0.0546 0.3924 0.039 Uiso 1 1 calc R
C14 C 0.15416(13) 0.02109(13) 0.49863(9) 0.0390(4) Uani 1 1 d .
H14 H 0.1443 -0.0481 0.4917 0.047 Uiso 1 1 calc R
C15 C 0.15458(10) 0.06040(13) 0.56732(9) 0.0308(4) Uani 1 1 d .
H15 H 0.1453 0.0182 0.6076 0.037 Uiso 1 1 calc R
C16 C 0.16845(10) 0.16125(12) 0.57775(8) 0.0279(3) Uani 1 1 d .
H16 H 0.1692 0.1880 0.6252 0.034 Uiso 1 1 calc R
C17 C 0.18123(9) 0.22332(11) 0.51900(8) 0.0242(3) Uani 1 1 d .
H17 H 0.1898 0.2927 0.5262 0.029 Uiso 1 1 calc R
C18 C 0.29978(8) 0.28676(11) 0.36199(7) 0.0197(3) Uani 1 1 d .
C19 C 0.35490(9) 0.23827(13) 0.40483(9) 0.0284(3) Uani 1 1 d .
H19 H 0.3389 0.1873 0.4373 0.034 Uiso 1 1 calc R
C20 C 0.43320(10) 0.26469(15) 0.39991(10) 0.0361(4) Uani 1 1 d .
H20 H 0.4706 0.2326 0.4298 0.043 Uiso 1 1 calc R
C21 C 0.45722(10) 0.33732(14) 0.35182(10) 0.0340(4) Uani 1 1 d .
H21 H 0.5108 0.3554 0.3491 0.041 Uiso 1 1 calc R
C22 C 0.40289(10) 0.38371(12) 0.30759(10) 0.0313(4) Uani 1 1 d .
H22 H 0.4196 0.4320 0.2734 0.038 Uiso 1 1 calc R
C23 C 0.32445(9) 0.35992(11) 0.31299(9) 0.0261(3) Uani 1 1 d .
H23 H 0.2873 0.3932 0.2835 0.031 Uiso 1 1 calc R
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'
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
N1 Ni1 Cl2 108.68(3)
N1 Ni1 Cl1 102.54(3)
Cl2 Ni1 Cl1 131.542(18)
N1 Ni1 P1 89.75(4)
Cl2 Ni1 P1 109.788(16)
Cl1 Ni1 P1 106.390(15)
C18 P1 C12 108.01(7)
C18 P1 C7 108.22(7)
C12 P1 C7 104.97(7)
C18 P1 Ni1 115.85(5)
C12 P1 Ni1 116.51(5)
C7 P1 Ni1 102.26(5)
C5 N1 C1 118.89(13)
C5 N1 Ni1 113.43(10)
C1 N1 Ni1 127.68(10)
N1 C1 C2 119.82(13)
N1 C1 C6 121.21(13)
C2 C1 C6 118.96(13)
C3 C2 C1 120.44(15)
C4 C3 C2 119.36(15)
C5 C4 C3 117.88(15)
N1 C5 C4 123.45(14)
C11 C6 C7 117.93(13)
C11 C6 C1 116.49(13)
C7 C6 C1 125.53(12)
C8 C7 C6 119.70(13)
C8 C7 P1 119.97(11)
C6 C7 P1 120.33(10)
C9 C8 C7 121.03(15)
C10 C9 C8 119.65(14)
C9 C10 C11 120.03(14)
C10 C11 C6 121.56(15)
C13 C12 C17 119.34(13)
C13 C12 P1 121.09(11)
C17 C12 P1 119.53(11)
C14 C13 C12 120.10(15)
C15 C14 C13 120.23(15)
C14 C15 C16 120.16(15)
C15 C16 C17 120.08(15)
C16 C17 C12 120.07(14)
C19 C18 C23 119.46(14)
C19 C18 P1 122.11(12)
C23 C18 P1 118.20(11)
C20 C19 C18 119.77(15)
C21 C20 C19 120.56(16)
C20 C21 C22 119.87(16)
C23 C22 C21 120.28(16)
C22 C23 C18 120.02(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 N1 2.0001(12)
Ni1 Cl2 2.2105(4)
Ni1 Cl1 2.2170(4)
Ni1 P1 2.2548(4)
P1 C18 1.8131(15)
P1 C12 1.8149(14)
P1 C7 1.8172(14)
N1 C5 1.3517(18)
N1 C1 1.3587(18)
C1 C2 1.393(2)
C1 C6 1.497(2)
C2 C3 1.385(2)
C3 C4 1.382(2)
C4 C5 1.377(2)
C6 C11 1.4022(19)
C6 C7 1.414(2)
C7 C8 1.398(2)
C8 C9 1.387(2)
C9 C10 1.383(2)
C10 C11 1.388(2)
C12 C13 1.392(2)
C12 C17 1.396(2)
C13 C14 1.389(2)
C14 C15 1.379(2)
C15 C16 1.385(2)
C16 C17 1.388(2)
C18 C19 1.394(2)
C18 C23 1.401(2)
C19 C20 1.388(2)
C20 C21 1.382(3)
C21 C22 1.387(2)
C22 C23 1.383(2)
