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#$Date: 2016-03-21 07:06:34 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178549 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/56/4065694.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_4065694
loop_
_publ_author_name
'Vicente, José'
'Arcas, Aurelia'
'Juliá-Hernández, Francisco'
'Bautista, Delia'
'Jones, Peter G.'
_publ_section_title
;
 Organometallic Complexes of Palladium(II) Derived from
 2,6-Diacetylpyridine Dimethylketal
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3066
_journal_paper_doi               10.1021/om100079x
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C13 H22 Cl3 N O4 Pd'
_chemical_formula_weight         469.07
_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                101.138(2)
_cell_angle_beta                 99.345(2)
_cell_angle_gamma                115.648(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6256(11)
_cell_length_b                   9.9998(11)
_cell_length_c                   11.0056(12)
_cell_measurement_reflns_used    5424
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.36
_cell_volume                     900.00(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10399
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    1.490
_exptl_absorpt_correction_T_max  0.9292
_exptl_absorpt_correction_T_min  0.7752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    'NH free, methyls rigid, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0254
_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)+(0.0199P)²+0.7414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0553
_reflns_number_gt                3758
_reflns_number_total             4013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100079x_si_002.cif
_cod_data_source_block           2173nas
_cod_database_code               4065694
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 0.579644(18) 0.640699(18) 0.645618(15) 0.01263(6) Uani 1 1 d .
Cl1 Cl 0.56608(6) 0.40193(6) 0.56171(5) 0.01707(11) Uani 1 1 d .
Cl2 Cl 0.73026(7) 0.67377(6) 0.84258(5) 0.02037(12) Uani 1 1 d .
Cl3 Cl 0.57351(7) 0.86675(6) 0.71710(5) 0.02043(12) Uani 1 1 d .
N1 N 0.2070(2) 0.7706(2) 0.79169(18) 0.0135(4) Uani 1 1 d .
H01 H 0.229(3) 0.754(3) 0.720(3) 0.024(7) Uiso 1 1 d .
O1 O 0.17373(18) 1.09914(17) 0.75630(15) 0.0181(3) Uani 1 1 d .
O2 O 0.24796(18) 0.93291(17) 0.63795(14) 0.0159(3) Uani 1 1 d .
O3 O 0.00728(17) 0.38194(17) 0.78892(15) 0.0162(3) Uani 1 1 d .
O4 O 0.15472(18) 0.50785(17) 0.65847(15) 0.0169(3) Uani 1 1 d .
C1 C 0.2199(2) 0.9120(2) 0.8398(2) 0.0146(4) Uani 1 1 d .
C2 C 0.1898(3) 0.9460(3) 0.9564(2) 0.0183(5) Uani 1 1 d .
H2 H 0.1979 1.0445 0.9919 0.022 Uiso 1 1 calc R
C3 C 0.1475(3) 0.8355(3) 1.0219(2) 0.0193(5) Uani 1 1 d .
H3 H 0.1258 0.8575 1.1024 0.023 Uiso 1 1 calc R
C4 C 0.1369(3) 0.6923(3) 0.9692(2) 0.0172(5) Uani 1 1 d .
H4 H 0.1100 0.6170 1.0146 0.021 Uiso 1 1 calc R
C5 C 0.1653(2) 0.6594(2) 0.8512(2) 0.0143(4) Uani 1 1 d .
C6 C 0.2698(3) 1.0255(2) 0.7604(2) 0.0157(4) Uani 1 1 d .
C7 C 0.4408(3) 1.1557(3) 0.8268(2) 0.0219(5) Uani 1 1 d .
H7A H 0.5150 1.1126 0.8280 0.033 Uiso 1 1 calc R
H7B H 0.4483 1.2050 0.9155 0.033 Uiso 1 1 calc R
H7C H 0.4690 1.2331 0.7797 0.033 Uiso 1 1 calc R
C8 C 0.0059(3) 0.9984(3) 0.6967(2) 0.0222(5) Uani 1 1 d .
H8A H -0.0106 0.9421 0.6077 0.033 Uiso 1 1 calc R
H8B H -0.0502 1.0600 0.6967 0.033 Uiso 1 1 calc R
H8C H -0.0365 0.9239 0.7447 0.033 Uiso 1 1 calc R
C9 C 0.3170(3) 1.0158(3) 0.5519(2) 0.0205(5) Uani 1 1 d .
H9A H 0.2879 1.0984 0.5520 0.031 Uiso 1 1 calc R
H9B H 0.2762 0.9441 0.4646 0.031 Uiso 1 1 calc R
H9C H 0.4340 1.0615 0.5804 0.031 Uiso 1 1 calc R
C10 C 0.1523(3) 0.5039(2) 0.7852(2) 0.0154(4) Uani 1 1 d .
C11 C 0.2868(3) 0.4838(3) 0.8576(2) 0.0199(5) Uani 1 1 d .
H11A H 0.2729 0.3808 0.8170 0.030 Uiso 1 1 calc R
H11B H 0.2842 0.4937 0.9474 0.030 Uiso 1 1 calc R
H11C H 0.3902 0.5639 0.8550 0.030 Uiso 1 1 calc R
C12 C -0.1355(3) 0.3783(3) 0.7201(2) 0.0201(5) Uani 1 1 d .
H12A H -0.1372 0.4742 0.7590 0.030 Uiso 1 1 calc R
H12B H -0.2303 0.2889 0.7247 0.030 Uiso 1 1 calc R
H12C H -0.1362 0.3694 0.6297 0.030 Uiso 1 1 calc R
C13 C 0.1389(3) 0.3702(3) 0.5740(2) 0.0225(5) Uani 1 1 d .
H13A H 0.2352 0.3602 0.6017 0.034 Uiso 1 1 calc R
H13B H 0.1263 0.3772 0.4857 0.034 Uiso 1 1 calc R
H13C H 0.0446 0.2791 0.5770 0.034 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'
O O 0.0106 0.0060 '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'
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
_geom_angle_site_symmetry_3
Cl3 Pd1 Cl2 92.25(2) .
Cl3 Pd1 Cl1 175.53(2) .
Cl2 Pd1 Cl1 91.53(2) .
Cl3 Pd1 Cl1 91.04(2) 2_666
Cl2 Pd1 Cl1 176.20(2) 2_666
Cl1 Pd1 Cl1 85.26(2) 2_666
Pd1 Cl1 Pd1 94.735(19) 2_666
C5 N1 C1 123.86(19) .
C6 O1 C8 115.45(17) .
C6 O2 C9 115.58(17) .
C10 O3 C12 114.45(16) .
C10 O4 C13 115.25(17) .
N1 C1 C2 118.9(2) .
N1 C1 C6 117.27(19) .
C2 C1 C6 123.86(19) .
C1 C2 C3 119.4(2) .
C2 C3 C4 119.7(2) .
C5 C4 C3 120.1(2) .
N1 C5 C4 118.1(2) .
N1 C5 C10 118.56(19) .
C4 C5 C10 123.37(19) .
O2 C6 O1 112.28(18) .
O2 C6 C7 114.94(18) .
O1 C6 C7 105.40(17) .
O2 C6 C1 104.44(16) .
O1 C6 C1 110.09(17) .
C7 C6 C1 109.71(18) .
O4 C10 O3 112.03(17) .
O4 C10 C11 114.27(18) .
O3 C10 C11 106.39(17) .
O4 C10 C5 104.23(16) .
O3 C10 C5 109.33(17) .
C11 C10 C5 110.58(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 Cl3 2.2750(6) .
Pd1 Cl2 2.2798(6) .
Pd1 Cl1 2.3259(6) .
Pd1 Cl1 2.3287(6) 2_666
Cl1 Pd1 2.3287(6) 2_666
N1 C5 1.344(3) .
N1 C1 1.353(3) .
O1 C6 1.410(3) .
O1 C8 1.431(3) .
O2 C6 1.405(3) .
O2 C9 1.434(3) .
O3 C10 1.415(2) .
O3 C12 1.439(3) .
O4 C10 1.407(3) .
O4 C13 1.436(3) .
C1 C2 1.373(3) .
C1 C6 1.526(3) .
C2 C3 1.386(3) .
C3 C4 1.389(3) .
C4 C5 1.378(3) .
C5 C10 1.525(3) .
C6 C7 1.525(3) .
C10 C11 1.518(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12A Cl2 0.98 2.89 3.814(2) 158.3 1_455
C2 H2 Cl2 0.95 2.77 3.689(2) 163.7 2_677
C11 H11A O1 0.98 2.46 3.398(3) 161.2 1_545
C7 H7A Cl3 0.98 2.85 3.713(2) 147.5 .
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_4
Cl3 Pd1 Cl1 Pd1 34.3(3) . 2_666
Cl2 Pd1 Cl1 Pd1 -177.95(2) . 2_666
Cl1 Pd1 Cl1 Pd1 0.0 2_666 2_666
C5 N1 C1 C2 0.4(3) . .
C5 N1 C1 C6 179.61(19) . .
N1 C1 C2 C3 0.1(3) . .
C6 C1 C2 C3 -179.1(2) . .
C1 C2 C3 C4 0.4(3) . .
C2 C3 C4 C5 -1.3(3) . .
C1 N1 C5 C4 -1.3(3) . .
C1 N1 C5 C10 178.92(19) . .
C3 C4 C5 N1 1.7(3) . .
C3 C4 C5 C10 -178.5(2) . .
C9 O2 C6 O1 73.0(2) . .
C9 O2 C6 C7 -47.5(2) . .
C9 O2 C6 C1 -167.75(17) . .
C8 O1 C6 O2 53.9(2) . .
C8 O1 C6 C7 179.75(18) . .
C8 O1 C6 C1 -62.0(2) . .
N1 C1 C6 O2 15.3(2) . .
C2 C1 C6 O2 -165.6(2) . .
N1 C1 C6 O1 136.00(19) . .
C2 C1 C6 O1 -44.8(3) . .
N1 C1 C6 C7 -108.4(2) . .
C2 C1 C6 C7 70.7(3) . .
C13 O4 C10 O3 -60.1(2) . .
C13 O4 C10 C11 61.0(2) . .
C13 O4 C10 C5 -178.20(17) . .
C12 O3 C10 O4 -52.1(2) . .
C12 O3 C10 C11 -177.68(17) . .
C12 O3 C10 C5 62.9(2) . .
N1 C5 C10 O4 -13.0(2) . .
C4 C5 C10 O4 167.2(2) . .
N1 C5 C10 O3 -132.93(19) . .
C4 C5 C10 O3 47.3(3) . .
N1 C5 C10 C11 110.2(2) . .
C4 C5 C10 C11 -69.5(3) . .
