#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:59:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178543 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/49/4064944.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_4064944
loop_
_publ_author_name
'Gwynne, Erin A.'
'Stephan, Douglas W.'
_publ_section_title
;
 Nickel(II) and Palladium(II) Bis-Aminophosphine Pincer Complexes
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              4128
_journal_paper_doi               10.1021/om200439q
_journal_volume                  30
_journal_year                    2011
_chemical_formula_sum            'C18 H41 Cl N2 Ni P2'
_chemical_formula_weight         441.63
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 99.861(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0239(11)
_cell_length_b                   14.246(2)
_cell_length_c                   10.4439(14)
_cell_measurement_temperature    150(2)
_cell_volume                     1176.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0699
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18769
_diffrn_reflns_theta_full        33.78
_diffrn_reflns_theta_max         33.78
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.5115
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         4858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0546
_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)+(0.0682P)²+0.3605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1550
_reflns_number_gt                3208
_reflns_number_total             4858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200439q_si_006.cif
_cod_data_source_block           eag034_0m
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               4064944
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
Ni1 Ni 0.78030(4) 0.2500 0.92386(3) 0.02998(13) Uani 1 2 d S
Cl1 Cl 0.95900(12) 0.21188(11) 0.79227(11) 0.0477(4) Uani 0.50 1 d P
P1 P 0.89100(9) 0.2500 1.13006(7) 0.0397(2) Uani 1 2 d S
P2 P 0.53596(8) 0.2500 0.79392(6) 0.02070(15) Uani 1 2 d S
N1 N 0.6949(3) 0.2500 1.0750(2) 0.0406(8) Uani 1 2 d S
N2 N 0.3823(3) 0.2500 0.8805(3) 0.0553(11) Uani 1 2 d S
H2A H 0.279(8) 0.263(7) 0.839(5) 0.066 Uiso 0.50 1 d P
C1 C 0.9604(6) 0.1421(4) 1.2219(3) 0.0964(17) Uani 1 1 d .
C2A C 0.9508(15) 0.0775(6) 1.1360(9) 0.086(3) Uani 0.50 1 d P
H2AA H 1.0546 0.0705 1.1007 0.129 Uiso 0.50 1 d P
H2AB H 0.9254 0.0166 1.1707 0.129 Uiso 0.50 1 d P
H2AC H 0.8603 0.0902 1.0620 0.129 Uiso 0.50 1 d P
C2B C 0.8303(10) 0.0498(5) 1.1262(6) 0.0584(17) Uani 0.50 1 d P
H2BA H 0.8615 -0.0105 1.1652 0.088 Uiso 0.50 1 d P
H2BB H 0.7158 0.0622 1.1224 0.088 Uiso 0.50 1 d P
H2BC H 0.8584 0.0489 1.0385 0.088 Uiso 0.50 1 d P
C3A C 1.1692(9) 0.1727(6) 1.2835(7) 0.073(2) Uani 0.50 1 d P
H3AA H 1.1729 0.2315 1.3298 0.109 Uiso 0.50 1 d P
H3AB H 1.2226 0.1250 1.3416 0.109 Uiso 0.50 1 d P
H3AC H 1.2335 0.1801 1.2133 0.109 Uiso 0.50 1 d P
C3B C 1.1225(12) 0.0952(8) 1.2227(12) 0.113(4) Uani 0.50 1 d P
H3BA H 1.2098 0.1314 1.2735 0.169 Uiso 0.50 1 d P
H3BB H 1.1163 0.0345 1.2678 0.169 Uiso 0.50 1 d P
H3BC H 1.1414 0.0847 1.1389 0.169 Uiso 0.50 1 d P
C4 C 0.8875(8) 0.1310(4) 1.3453(4) 0.112(2) Uani 1 1 d .
H4A H 0.9293 0.0726 1.3890 0.168 Uiso 1 1 calc R
H4B H 0.7638 0.1289 1.3239 0.168 Uiso 1 1 calc R
H4C H 0.9221 0.1843 1.4030 0.168 Uiso 1 1 calc R
C5 C 0.5305(4) 0.2500 1.1084(3) 0.0569(13) Uani 1 2 d S
H5A H 0.508(10) 0.314(5) 1.093(7) 0.068 Uiso 0.50 1 d P
H5B H 0.515(9) 0.214(4) 1.189(6) 0.068 Uiso 0.50 1 d P
C6 C 0.4020(6) 0.1934(6) 1.0077(4) 0.0552(17) Uani 0.50 1 d P
H6A H 0.286(9) 0.213(4) 1.042(6) 0.066 Uiso 0.50 1 d P
H6B H 0.432(10) 0.123(5) 0.998(7) 0.066 Uiso 0.50 1 d P
C7 C 0.4963(5) 0.1427(2) 0.6913(4) 0.0745(12) Uani 1 1 d .
C8 C 0.6082(12) 0.1397(6) 0.5894(8) 0.217(5) Uani 1 1 d .
H8A H 0.5843 0.0826 0.5372 0.326 Uiso 1 1 calc R
H8B H 0.7271 0.1396 0.6317 0.326 Uiso 1 1 calc R
H8C H 0.5862 0.1949 0.5330 0.326 Uiso 1 1 calc R
C9 C 0.5394(7) 0.0617(3) 0.7884(7) 0.155(4) Uani 1 1 d .
H9A H 0.5223 0.0017 0.7421 0.233 Uiso 1 1 calc R
H9B H 0.4656 0.0647 0.8539 0.233 Uiso 1 1 calc R
H9C H 0.6577 0.0669 0.8310 0.233 Uiso 1 1 calc R
C10 C 0.3102(6) 0.1315(3) 0.6286(5) 0.112(2) Uani 1 1 d .
H10A H 0.2967 0.0744 0.5754 0.169 Uiso 1 1 calc R
H10B H 0.2744 0.1861 0.5736 0.169 Uiso 1 1 calc R
H10C H 0.2403 0.1268 0.6967 0.169 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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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
N1 Ni1 P1 45.34(8) . .
N1 Ni1 P2 96.15(8) . .
P1 Ni1 P2 141.49(3) . .
N1 Ni1 Cl1 156.15(7) . 4_565
P1 Ni1 Cl1 114.47(4) . 4_565
P2 Ni1 Cl1 102.81(4) . 4_565
N1 Ni1 Cl1 156.15(7) . .
P1 Ni1 Cl1 114.47(4) . .
P2 Ni1 Cl1 102.81(4) . .
Cl1 Ni1 Cl1 28.36(8) 4_565 .
Cl1 Cl1 Ni1 75.82(4) 4_565 .
N1 P1 C1 112.45(18) . 4_565
N1 P1 C1 112.45(19) . .
C1 P1 C1 112.7(3) 4_565 .
N1 P1 Ni1 55.23(9) . .
C1 P1 Ni1 123.19(16) 4_565 .
C1 P1 Ni1 123.19(16) . .
N2 P2 C7 104.21(16) . 4_565
N2 P2 C7 104.21(16) . .
C7 P2 C7 110.3(3) 4_565 .
N2 P2 Ni1 109.56(10) . .
C7 P2 Ni1 113.83(10) 4_565 .
C7 P2 Ni1 113.83(10) . .
C5 N1 P1 145.0(2) . .
C5 N1 Ni1 135.6(2) . .
P1 N1 Ni1 79.43(11) . .
C6 N2 C6 63.2(6) 4_565 .
C6 N2 P2 119.8(3) 4_565 .
C6 N2 P2 119.8(3) . .
C2A C1 C3B 67.8(7) . .
C2A C1 C4 122.5(7) . .
C3B C1 C4 114.9(6) . .
C2A C1 C3A 112.2(7) . .
C3B C1 C3A 46.7(5) . .
C4 C1 C3A 101.5(4) . .
C2A C1 P1 105.0(4) . .
C3B C1 P1 124.9(6) . .
C4 C1 P1 113.8(4) . .
C3A C1 P1 99.7(4) . .
C2A C1 C2B 32.1(6) . .
C3B C1 C2B 95.6(6) . .
C4 C1 C2B 96.9(4) . .
C3A C1 C2B 142.2(5) . .
P1 C1 C2B 102.6(3) . .
C2B C2A C1 106.7(11) . .
C2B C2A C3B 148.4(11) . .
C1 C2A C3B 61.8(6) . .
C2A C2B C1 41.2(6) . .
C3B C3A C1 55.1(5) . .
C3A C3B C1 78.2(7) . .
C3A C3B C2A 125.8(7) . .
C1 C3B C2A 50.5(5) . .
N1 C5 C6 111.6(3) . 4_565
N1 C5 C6 111.6(3) . .
C6 C5 C6 62.1(6) 4_565 .
N2 C6 C5 105.6(4) . .
N2 C6 C6 58.4(3) . 4_565
C5 C6 C6 59.0(3) . 4_565
C8 C7 C9 110.5(5) . .
C8 C7 C10 110.5(5) . .
C9 C7 C10 107.2(4) . .
C8 C7 P2 111.5(4) . .
C9 C7 P2 103.9(3) . .
C10 C7 P2 112.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 1.825(2) .
Ni1 P1 2.1844(8) .
Ni1 P2 2.1850(8) .
Ni1 Cl1 2.2168(11) 4_565
Ni1 Cl1 2.2168(11) .
Cl1 Cl1 1.086(3) 4_565
P1 N1 1.580(3) .
P1 C1 1.847(4) 4_565
P1 C1 1.847(4) .
P2 N2 1.649(3) .
P2 C7 1.862(3) 4_565
P2 C7 1.862(3) .
N1 C5 1.421(4) .
N2 C6 1.539(6) 4_565
N2 C6 1.539(6) .
C1 C2A 1.278(10) .
C1 C3B 1.461(10) .
C1 C4 1.512(6) .
C1 C3A 1.745(10) .
C1 C2B 1.860(9) .
C2A C2B 1.033(12) .
C2A C3B 1.534(14) .
C3A C3B 1.297(13) .
C5 C6 1.564(6) 4_565
C5 C6 1.564(6) .
C6 C6 1.613(17) 4_565
C7 C8 1.506(9) .
C7 C9 1.536(6) .
C7 C10 1.533(5) .
