#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:45:20 +0100 (lun 21 de mar de 2016) $
#$Revision: 178580 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/91/4069121.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_4069121
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 New Pyridine-Phosphine Ligands and
 Their Use in Ethene Oligomerization
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              3272
_journal_paper_doi               10.1021/om900038u
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C22 H25 Cl N O2 P Pd'
_chemical_formula_sum            'C22 H25 Cl N O2 P Pd'
_chemical_formula_weight         508.25
_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_method           SHELXL-97
_cell_angle_alpha                103.680(15)
_cell_angle_beta                 106.062(18)
_cell_angle_gamma                99.75(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3871(10)
_cell_length_b                   12.376(2)
_cell_length_c                   13.626(2)
_cell_measurement_reflns_used    17132
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     1278.2(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26835
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_platon_squeeze_details
;
;
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0251
_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)+(0.0373P)²+0.7190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                5478
_reflns_number_total             5829
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om900038u_si_004.cif
_cod_data_source_block           s3614a
_cod_database_code               4069121
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
Pd1 Pd 0.778077(16) 0.199187(11) 0.289886(10) 0.01736(6) Uani 1 1 d .
Cl1 Cl 0.60758(6) 0.15553(4) 0.39567(4) 0.02693(11) Uani 1 1 d .
P2 P 0.94715(6) 0.25462(4) 0.20192(3) 0.01637(10) Uani 1 1 d .
O1 O 1.13926(18) 0.22659(13) 0.04180(11) 0.0288(3) Uani 1 1 d .
O2 O 1.1215(2) 0.45411(13) 0.38556(12) 0.0395(4) Uani 1 1 d .
N1 N 0.9200(2) 0.07712(14) 0.33292(12) 0.0204(3) Uani 1 1 d .
C1 C 1.0929(2) 0.10253(16) 0.37031(13) 0.0194(3) Uani 1 1 d .
C2 C 1.1790(3) 0.02416(18) 0.40536(15) 0.0256(4) Uani 1 1 d .
H2 H 1.3007 0.0439 0.4333 0.031 Uiso 1 1 calc R
C3 C 1.0863(3) -0.08214(18) 0.39925(16) 0.0309(5) Uani 1 1 d .
H3 H 1.1432 -0.1358 0.4235 0.037 Uiso 1 1 calc R
C4 C 0.9091(3) -0.10933(18) 0.35723(17) 0.0309(5) Uani 1 1 d .
H4 H 0.8426 -0.1828 0.3501 0.037 Uiso 1 1 calc R
C5 C 0.8308(3) -0.02746(17) 0.32587(16) 0.0263(4) Uani 1 1 d .
H5 H 0.7092 -0.0457 0.2982 0.032 Uiso 1 1 calc R
C6 C 1.1894(2) 0.21753(17) 0.37362(14) 0.0212(4) Uani 1 1 d .
H6A H 1.3134 0.2271 0.4088 0.025 Uiso 1 1 calc R
H6B H 1.1533 0.2783 0.4175 0.025 Uiso 1 1 calc R
C7 C 1.1606(2) 0.23326(16) 0.26147(15) 0.0207(4) Uani 1 1 d .
H7A H 1.1750 0.1646 0.2135 0.025 Uiso 1 1 calc R
H7B H 1.2491 0.3004 0.2668 0.025 Uiso 1 1 calc R
C8 C 0.8687(2) 0.17374(15) 0.06013(14) 0.0193(3) Uani 1 1 d .
C9 C 0.9720(2) 0.16567(16) -0.00541(14) 0.0207(4) Uani 1 1 d .
C10 C 0.9020(3) 0.09992(17) -0.11265(15) 0.0249(4) Uani 1 1 d .
H10 H 0.9734 0.0919 -0.1559 0.030 Uiso 1 1 calc R
C11 C 0.7284(3) 0.04619(17) -0.15627(15) 0.0272(4) Uani 1 1 d .
H11 H 0.6810 0.0026 -0.2297 0.033 Uiso 1 1 calc R
C12 C 0.6234(3) 0.05560(18) -0.09356(16) 0.0277(4) Uani 1 1 d .
H12 H 0.5042 0.0197 -0.1239 0.033 Uiso 1 1 calc R
C13 C 0.6946(3) 0.11810(17) 0.01404(15) 0.0239(4) Uani 1 1 d .
H13 H 0.6230 0.1231 0.0573 0.029 Uiso 1 1 calc R
C14 C 1.2531(3) 0.2083(2) -0.01825(18) 0.0383(5) Uani 1 1 d .
H14A H 1.2543 0.1270 -0.0367 0.058 Uiso 1 1 calc R
H14B H 1.3690 0.2555 0.0248 0.058 Uiso 1 1 calc R
H14C H 1.2139 0.2299 -0.0839 0.058 Uiso 1 1 calc R
C15 C 0.9821(3) 0.40430(16) 0.20160(15) 0.0218(4) Uani 1 1 d .
C16 C 1.0657(3) 0.49166(17) 0.29910(16) 0.0290(4) Uani 1 1 d .
C17 C 1.0881(4) 0.60635(19) 0.30352(19) 0.0410(6) Uani 1 1 d .
H17 H 1.1459 0.6648 0.3697 0.049 Uiso 1 1 calc R
C18 C 1.0253(4) 0.6349(2) 0.2102(2) 0.0461(6) Uani 1 1 d .
H18 H 1.0419 0.7135 0.2126 0.055 Uiso 1 1 calc R
C19 C 0.9389(4) 0.5507(2) 0.11397(19) 0.0437(6) Uani 1 1 d .
H19 H 0.8945 0.5712 0.0508 0.052 Uiso 1 1 calc R
C20 C 0.9172(3) 0.43563(18) 0.10986(17) 0.0314(5) Uani 1 1 d .
H20 H 0.8574 0.3777 0.0436 0.038 Uiso 1 1 calc R
C21 C 1.2069(5) 0.5393(2) 0.48813(19) 0.0623(9) Uani 1 1 d .
H21A H 1.3148 0.5842 0.4880 0.093 Uiso 1 1 calc R
H21B H 1.2308 0.5011 0.5440 0.093 Uiso 1 1 calc R
H21C H 1.1331 0.5904 0.5022 0.093 Uiso 1 1 calc R
C22 C 0.6321(3) 0.3062(2) 0.24224(17) 0.0319(5) Uani 1 1 d .
H22A H 0.6372 0.3126 0.1728 0.048 Uiso 1 1 calc R
H22B H 0.6762 0.3824 0.2953 0.048 Uiso 1 1 calc R
H22C H 0.5130 0.2749 0.2358 0.048 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'
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'
Pd Pd -0.9988 1.0072 '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
C22 Pd1 N1 176.44(8)
C22 Pd1 P2 88.68(7)
N1 Pd1 P2 92.22(4)
C22 Pd1 Cl1 89.94(7)
N1 Pd1 Cl1 89.45(4)
P2 Pd1 Cl1 175.035(17)
C8 P2 C15 103.56(9)
C8 P2 C7 107.89(9)
C15 P2 C7 106.17(9)
C8 P2 Pd1 113.03(7)
C15 P2 Pd1 116.96(6)
C7 P2 Pd1 108.69(6)
C9 O1 C14 117.49(16)
C16 O2 C21 117.72(18)
C5 N1 C1 118.77(17)
C5 N1 Pd1 118.15(13)
C1 N1 Pd1 123.03(13)
N1 C1 C2 121.01(18)
N1 C1 C6 117.86(16)
C2 C1 C6 121.12(17)
C3 C2 C1 119.7(2)
C2 C3 C4 119.02(19)
C5 C4 C3 118.7(2)
N1 C5 C4 122.7(2)
C1 C6 C7 112.94(15)
C6 C7 P2 113.13(13)
C13 C8 C9 118.31(16)
C13 C8 P2 117.64(14)
C9 C8 P2 124.04(14)
O1 C9 C10 123.58(17)
O1 C9 C8 116.17(16)
C10 C9 C8 120.24(18)
C11 C10 C9 120.06(18)
C10 C11 C12 120.53(18)
C11 C12 C13 119.25(18)
C12 C13 C8 121.55(18)
C20 C15 C16 118.40(18)
C20 C15 P2 122.49(15)
C16 C15 P2 118.91(15)
O2 C16 C17 124.12(19)
O2 C16 C15 114.89(17)
C17 C16 C15 121.0(2)
C16 C17 C18 119.3(2)
C19 C18 C17 120.8(2)
C18 C19 C20 119.7(2)
C15 C20 C19 120.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C22 2.047(2)
Pd1 N1 2.1644(17)
Pd1 P2 2.2177(6)
Pd1 Cl1 2.3794(6)
P2 C8 1.8237(18)
P2 C15 1.8271(19)
P2 C7 1.8412(19)
O1 C9 1.365(2)
O1 C14 1.432(2)
O2 C16 1.360(3)
O2 C21 1.439(3)
N1 C5 1.348(3)
N1 C1 1.350(2)
C1 C2 1.398(3)
C1 C6 1.497(3)
C2 C3 1.381(3)
C3 C4 1.385(3)
C4 C5 1.384(3)
C6 C7 1.544(3)
C8 C13 1.396(3)
C8 C9 1.405(3)
C9 C10 1.394(3)
C10 C11 1.386(3)
C11 C12 1.387(3)
C12 C13 1.388(3)
C15 C20 1.390(3)
C15 C16 1.405(3)
C16 C17 1.384(3)
C17 C18 1.388(4)
C18 C19 1.379(4)
C19 C20 1.390(3)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 1.000 285 35 ' '
