#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:43:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178403 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/24/4022465.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_4022465
loop_
_publ_author_name
'Jan K. Eberhardt'
'Roland Fröhlich'
'Ernst-Ulrich Würthwein'
_publ_section_title
;
 N-Acylamidine Palladium(II) Complexes. Synthesis, Structures,
 and Catalytic Activity for Suzuki-Miyaura Cross-Coupling
 Reactions: Experiments and DFT Calculations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6690
_journal_page_last               6694
_journal_paper_doi               10.1021/jo034455t
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C32 H48 Cl2 N4 O2 Pd'
_chemical_formula_weight         698.04
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   'at N4 from difmap, others geom'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.56(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.716(1)
_cell_length_b                   15.786(1)
_cell_length_c                   10.911(1)
_cell_measurement_temperature    198(2)
_cell_volume                     1716.6(2)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode Nonius FR591''
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16397
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  0.8679
_exptl_absorpt_correction_T_min  0.7350
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995 & 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.980
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    'refined as riding atoms'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         5216
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0228P)²+0.6581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0660
_reflns_number_gt                4461
_reflns_number_total             5216
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034455tsi20030709_093311.cif
_cod_data_source_block           wue1784
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022465
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd 0.0000 0.0000 0.0000 0.02089(5) Uani 1 2 d S . .
C1 C -0.05526(17) 0.25570(10) -0.27273(16) 0.0382(4) Uani 1 1 d D . .
C2 C 0.06639(16) 0.19720(10) -0.24063(16) 0.0332(3) Uani 1 1 d . A .
O3 O 0.17463(13) 0.22053(8) -0.23776(16) 0.0525(3) Uani 1 1 d . . .
N4 N 0.04445(13) 0.11428(8) -0.21024(13) 0.0305(3) Uani 1 1 d . . .
H4 H -0.0234(19) 0.1022(12) -0.2034(18) 0.037 Uiso 1 1 d . . .
C5 C 0.13531(13) 0.04771(9) -0.18036(13) 0.0236(3) Uani 1 1 d . A .
C51 C 0.23671(13) 0.04744(9) -0.24422(13) 0.0247(3) Uani 1 1 d . . .
C52 C 0.37285(14) 0.04716(10) -0.16792(15) 0.0310(3) Uani 1 1 d . A .
H52 H 0.4018 0.0466 -0.0745 0.037 Uiso 1 1 calc R . .
C53 C 0.46651(16) 0.04771(12) -0.22825(18) 0.0406(4) Uani 1 1 d . . .
H53 H 0.5597 0.0482 -0.1761 0.049 Uiso 1 1 calc R A .
C54 C 0.42440(19) 0.04753(13) -0.3637(2) 0.0469(4) Uani 1 1 d . A .
H54 H 0.4887 0.0475 -0.4047 0.056 Uiso 1 1 calc R . .
C55 C 0.2894(2) 0.04734(14) -0.44007(17) 0.0480(5) Uani 1 1 d . . .
H55 H 0.2609 0.0469 -0.5334 0.058 Uiso 1 1 calc R A .
C56 C 0.19482(16) 0.04785(12) -0.38047(15) 0.0358(3) Uani 1 1 d . A .
H56 H 0.1018 0.0485 -0.4330 0.043 Uiso 1 1 calc R . .
N6 N 0.12193(11) -0.01147(7) -0.10471(11) 0.0235(2) Uani 1 1 d . . .
C7 C 0.19208(14) -0.09371(9) -0.09047(14) 0.0284(3) Uani 1 1 d . A .
H7A H 0.2366 -0.1073 0.0043 0.034 Uiso 1 1 calc R . .
H7B H 0.2622 -0.0895 -0.1291 0.034 Uiso 1 1 calc R . .
C8 C 0.09466(16) -0.16458(10) -0.15879(15) 0.0320(3) Uani 1 1 d . . .
H8A H 0.1423 -0.2195 -0.1366 0.038 Uiso 1 1 calc R A .
H8B H 0.0210 -0.1656 -0.1245 0.038 Uiso 1 1 calc R . .
C9 C 0.03464(18) -0.15522(11) -0.30799(16) 0.0382(4) Uani 1 1 d . A .
H9A H -0.0127 -0.1002 -0.3306 0.046 Uiso 1 1 calc R . .
H9B H 0.1079 -0.1549 -0.3428 0.046 Uiso 1 1 calc R . .
C10 C -0.0629(2) -0.22616(14) -0.3736(2) 0.0578(5) Uani 1 1 d . . .
H10A H -0.0156 -0.2806 -0.3545 0.087 Uiso 1 1 calc R A .
H10B H -0.1003 -0.2170 -0.4691 0.087 Uiso 1 1 calc R . .
H10C H -0.1357 -0.2267 -0.3395 0.087 Uiso 1 1 calc R . .
C11A C -0.1792(5) 0.2164(4) -0.3739(7) 0.0699(17) Uani 0.623(14) 1 d PD A 1
H11A H -0.2528 0.2575 -0.3992 0.105 Uiso 0.623(14) 1 calc PR A 1
H11B H -0.2050 0.1661 -0.3361 0.105 Uiso 0.623(14) 1 calc PR A 1
H11C H -0.1600 0.2000 -0.4518 0.105 Uiso 0.623(14) 1 calc PR A 1
C12A C -0.0162(8) 0.3378(3) -0.3243(10) 0.066(2) Uani 0.623(14) 1 d PD A 1
H12A H 0.0007 0.3259 -0.4050 0.098 Uiso 0.623(14) 1 calc PR A 1
H12B H 0.0652 0.3612 -0.2574 0.098 Uiso 0.623(14) 1 calc PR A 1
H12C H -0.0894 0.3789 -0.3434 0.098 Uiso 0.623(14) 1 calc PR A 1
C13A C -0.0735(8) 0.2744(5) -0.1436(4) 0.0596(15) Uani 0.623(14) 1 d PD A 1
H13A H 0.0121 0.2931 -0.0778 0.089 Uiso 0.623(14) 1 calc PR A 1
H13B H -0.1036 0.2230 -0.1123 0.089 Uiso 0.623(14) 1 calc PR A 1
H13C H -0.1407 0.3192 -0.1576 0.089 Uiso 0.623(14) 1 calc PR A 1
C11B C -0.1914(6) 0.2087(5) -0.3183(14) 0.068(3) Uani 0.377(14) 1 d PD A 2
H11D H -0.2647 0.2500 -0.3492 0.102 Uiso 0.377(14) 1 calc PR A 2
H11E H -0.1985 0.1765 -0.2443 0.102 Uiso 0.377(14) 1 calc PR A 2
H11F H -0.1973 0.1698 -0.3902 0.102 Uiso 0.377(14) 1 calc PR A 2
C12B C -0.0661(10) 0.3183(5) -0.3837(8) 0.0477(19) Uani 0.377(14) 1 d PD A 2
H12D H -0.0887 0.2874 -0.4670 0.072 Uiso 0.377(14) 1 calc PR A 2
H12E H 0.0198 0.3475 -0.3636 0.072 Uiso 0.377(14) 1 calc PR A 2
H12F H -0.1365 0.3599 -0.3915 0.072 Uiso 0.377(14) 1 calc PR A 2
C13B C -0.0423(13) 0.3045(7) -0.1476(6) 0.061(3) Uani 0.377(14) 1 d PD A 2
H13D H 0.0412 0.3373 -0.1180 0.091 Uiso 0.377(14) 1 calc PR A 2
H13E H -0.0410 0.2646 -0.0785 0.091 Uiso 0.377(14) 1 calc PR A 2
H13F H -0.1187 0.3431 -0.1662 0.091 Uiso 0.377(14) 1 calc PR A 2
Cl1 Cl 0.18888(4) 0.01168(3) 0.18884(4) 0.03400(9) Uani 1 1 d . . .
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'
Pd Pd -0.9988 1.0072 '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'
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
N6 Pd N6 180.00(4) 3 .
N6 Pd Cl1 91.44(4) 3 .
N6 Pd Cl1 88.56(4) . .
N6 Pd Cl1 88.56(4) 3 3
N6 Pd Cl1 91.44(4) . 3
Cl1 Pd Cl1 180.00(3) . 3
C11A C1 C13A 112.2(3) . .
C11A C1 C13B 128.7(5) . .
C13A C1 C13B 22.4(4) . .
C11A C1 C2 111.4(3) . .
C13A C1 C2 107.1(3) . .
C13B C1 C2 108.0(5) . .
C11A C1 C12A 111.4(3) . .
C13A C1 C12A 108.7(3) . .
C13B C1 C12A 87.3(4) . .
C2 C1 C12A 105.7(2) . .
C11A C1 C12B 84.1(3) . .
C13A C1 C12B 127.5(4) . .
C13B C1 C12B 109.6(4) . .
C2 C1 C12B 112.4(3) . .
C12A C1 C12B 27.9(2) . .
C11A C1 C11B 25.5(4) . .
C13A C1 C11B 87.9(5) . .
C13B C1 C11B 107.1(4) . .
C2 C1 C11B 114.1(4) . .
C12A C1 C11B 129.8(4) . .
C12B C1 C11B 105.4(3) . .
O3 C2 N4 121.74(15) . .
O3 C2 C1 123.52(15) . .
N4 C2 C1 114.71(13) . .
C5 N4 C2 127.09(12) . .
N6 C5 N4 117.76(12) . .
N6 C5 C51 124.67(12) . .
N4 C5 C51 117.48(12) . .
C56 C51 C52 119.86(13) . .
C56 C51 C5 119.79(12) . .
C52 C51 C5 120.35(12) . .
C53 C52 C51 119.94(14) . .
C54 C53 C52 119.99(15) . .
C53 C54 C55 120.39(15) . .
C54 C55 C56 120.01(16) . .
C51 C56 C55 119.81(15) . .
C5 N6 C7 122.10(11) . .
C5 N6 Pd 122.72(9) . .
C7 N6 Pd 115.17(8) . .
N6 C7 C8 111.24(11) . .
C9 C8 C7 113.33(13) . .
C10 C9 C8 112.30(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd N6 2.0353(11) 3
Pd N6 2.0353(11) .
Pd Cl1 2.3046(5) .
Pd Cl1 2.3046(5) 3
C1 C11A 1.513(3) .
C1 C13A 1.520(3) .
C1 C13B 1.529(4) .
C1 C2 1.530(2) .
C1 C12A 1.531(3) .
C1 C12B 1.534(3) .
C1 C11B 1.547(4) .
C2 O3 1.2063(19) .
C2 N4 1.391(2) .
N4 C5 1.3876(18) .
C5 N6 1.2890(17) .
C5 C51 1.4908(18) .
C51 C56 1.386(2) .
C51 C52 1.3887(19) .
C52 C53 1.388(2) .
C53 C54 1.377(3) .
C54 C55 1.379(3) .
C55 C56 1.391(2) .
N6 C7 1.4796(17) .
C7 C8 1.525(2) .
C8 C9 1.522(2) .
C9 C10 1.519(3) .
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
C11A C1 C2 O3 132.1(4) .
C13A C1 C2 O3 -104.8(4) .
C13B C1 C2 O3 -81.3(6) .
C12A C1 C2 O3 11.0(5) .
C12B C1 C2 O3 39.7(5) .
C11B C1 C2 O3 159.7(6) .
C11A C1 C2 N4 -49.9(4) .
C13A C1 C2 N4 73.2(4) .
C13B C1 C2 N4 96.7(6) .
C12A C1 C2 N4 -171.0(4) .
C12B C1 C2 N4 -142.3(5) .
C11B C1 C2 N4 -22.3(7) .
O3 C2 N4 C5 -3.5(3) .
C1 C2 N4 C5 178.46(14) .
C2 N4 C5 N6 151.75(15) .
C2 N4 C5 C51 -31.6(2) .
N6 C5 C51 C56 118.37(17) .
N4 C5 C51 C56 -58.0(2) .
N6 C5 C51 C52 -61.9(2) .
N4 C5 C51 C52 121.67(16) .
C56 C51 C52 C53 0.3(2) .
C5 C51 C52 C53 -179.40(15) .
C51 C52 C53 C54 -0.8(3) .
C52 C53 C54 C55 0.4(3) .
C53 C54 C55 C56 0.4(3) .
C52 C51 C56 C55 0.5(3) .
C5 C51 C56 C55 -179.81(16) .
C54 C55 C56 C51 -0.8(3) .
N4 C5 N6 C7 166.00(13) .
C51 C5 N6 C7 -10.4(2) .
N4 C5 N6 Pd -12.48(18) .
C51 C5 N6 Pd 171.11(10) .
N6 Pd N6 C5 132(100) 3
Cl1 Pd N6 C5 -108.02(11) .
Cl1 Pd N6 C5 71.98(11) 3
N6 Pd N6 C7 -47(100) 3
Cl1 Pd N6 C7 73.40(9) .
Cl1 Pd N6 C7 -106.60(9) 3
C5 N6 C7 C8 -107.96(15) .
Pd N6 C7 C8 70.63(13) .
N6 C7 C8 C9 66.62(16) .
C7 C8 C9 C10 -179.53(15) .
