#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:17:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178557 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/65/4066512.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_4066512
loop_
_publ_author_name
'Fliedel, Christophe'
'Braunstein, Pierre'
_publ_section_title
;
 Thioether-Functionalized N-Heterocyclic Carbenes: Mono- and Bis-(S,CNHC)
 Palladium Complexes, Catalytic C−C Coupling, and Characterization
 of a Unique Ag4I4(S,CNHC)2Planar Cluster†
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5614
_journal_paper_doi               10.1021/om100500y
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C22 H40 Cl2 N4 Pd S2'
_chemical_formula_sum            'C22 H40 Cl2 N4 Pd S2'
_chemical_formula_weight         602.00
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                109.441(3)
_cell_angle_beta                 90.829(3)
_cell_angle_gamma                98.612(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9669(5)
_cell_length_b                   12.5972(6)
_cell_length_c                   15.1836(6)
_cell_measurement_reflns_used    9356
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      0.998
_cell_volume                     1417.37(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0610
_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       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9715
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         1.43
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.102
_refine_diff_density_min         -1.309
_refine_diff_density_rms         0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         6457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0728P)²+0.1662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1387
_reflns_number_gt                4265
_reflns_number_total             6457
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100500y_si_002.cif
_cod_data_source_block           gilles5
_cod_original_cell_volume        1417.37(12)
_cod_database_code               4066512
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 0.5000 0.0000 0.5000 0.03156(14) Uani 1 2 d S
Pd2 Pd 1.0000 0.0000 1.0000 0.03721(14) Uani 1 2 d S
Cl1 Cl 0.65075(15) -0.01092(10) 0.62691(7) 0.0461(3) Uani 1 1 d .
Cl2 Cl 1.14360(16) -0.01262(11) 0.86686(7) 0.0518(3) Uani 1 1 d .
C1 C 0.3385(5) 0.0859(3) 0.5875(2) 0.0333(9) Uani 1 1 d .
C2 C 0.2041(6) 0.2254(4) 0.6757(3) 0.0447(11) Uani 1 1 d .
H2 H 0.1747 0.2972 0.7037 0.054 Uiso 1 1 calc R
C3 C 0.1325(6) 0.1281(4) 0.6873(3) 0.0450(11) Uani 1 1 d .
H3 H 0.0434 0.1193 0.7245 0.054 Uiso 1 1 calc R
C4 C 0.1741(6) -0.0773(3) 0.6209(3) 0.0390(9) Uani 1 1 d .
H4A H 0.1268 -0.0858 0.6771 0.047 Uiso 1 1 calc R
H4B H 0.2764 -0.1118 0.6111 0.047 Uiso 1 1 calc R
C5 C 0.0457(6) -0.1385(3) 0.5376(3) 0.0398(10) Uani 1 1 d .
H5A H 0.0933 -0.1293 0.4816 0.048 Uiso 1 1 calc R
H5B H -0.0561 -0.1035 0.5476 0.048 Uiso 1 1 calc R
C6 C -0.1320(6) -0.2832(4) 0.6208(3) 0.0510(12) Uani 1 1 d .
H6A H -0.0566 -0.2520 0.6773 0.061 Uiso 1 1 calc R
H6B H -0.2166 -0.2340 0.6255 0.061 Uiso 1 1 calc R
C7 C -0.2184(8) -0.4024(4) 0.6109(4) 0.0754(17) Uani 1 1 d .
H7A H -0.2998 -0.4303 0.5578 0.113 Uiso 1 1 calc R
H7B H -0.2754 -0.4007 0.6665 0.113 Uiso 1 1 calc R
H7C H -0.1347 -0.4518 0.6020 0.113 Uiso 1 1 calc R
C8 C 0.4433(6) 0.2783(3) 0.5824(3) 0.0448(11) Uani 1 1 d .
H8A H 0.3971 0.3487 0.5965 0.054 Uiso 1 1 calc R
H8B H 0.4477 0.2466 0.5150 0.054 Uiso 1 1 calc R
C9 C 0.6221(7) 0.3047(4) 0.6278(3) 0.0588(13) Uani 1 1 d .
H9A H 0.6681 0.2341 0.6120 0.071 Uiso 1 1 calc R
H9B H 0.6920 0.3544 0.6009 0.071 Uiso 1 1 calc R
C10 C 0.6380(7) 0.3597(5) 0.7316(3) 0.0649(14) Uani 1 1 d .
H10A H 0.5667 0.3113 0.7591 0.078 Uiso 1 1 calc R
H10B H 0.5966 0.4319 0.7480 0.078 Uiso 1 1 calc R
C11 C 0.8227(7) 0.3810(5) 0.7737(4) 0.0796(17) Uani 1 1 d .
H11A H 0.8632 0.3096 0.7597 0.119 Uiso 1 1 calc R
H11B H 0.8257 0.4173 0.8404 0.119 Uiso 1 1 calc R
H11C H 0.8939 0.4295 0.7473 0.119 Uiso 1 1 calc R
C12 C 0.8351(5) 0.0860(3) 0.9595(3) 0.0389(10) Uani 1 1 d .
C13 C 0.6993(6) 0.2259(4) 0.9480(3) 0.0506(11) Uani 1 1 d .
H13 H 0.6706 0.2980 0.9595 0.061 Uiso 1 1 calc R
C14 C 0.6250(6) 0.1281(4) 0.8830(3) 0.0503(11) Uani 1 1 d .
H14 H 0.5339 0.1194 0.8408 0.060 Uiso 1 1 calc R
C15 C 0.6654(6) -0.0785(3) 0.8364(3) 0.0437(10) Uani 1 1 d .
H15A H 0.7678 -0.1127 0.8265 0.052 Uiso 1 1 calc R
H15B H 0.6134 -0.0876 0.7757 0.052 Uiso 1 1 calc R
C16 C 0.5428(6) -0.1395(3) 0.8865(3) 0.0443(10) Uani 1 1 d .
H16A H 0.4401 -0.1055 0.8956 0.053 Uiso 1 1 calc R
H16B H 0.5944 -0.1289 0.9477 0.053 Uiso 1 1 calc R
C17 C 0.3575(7) -0.2879(4) 0.7244(3) 0.0556(13) Uani 1 1 d .
H17A H 0.2713 -0.2403 0.7467 0.067 Uiso 1 1 calc R
H17B H 0.4278 -0.2567 0.6844 0.067 Uiso 1 1 calc R
C18 C 0.2732(9) -0.4099(5) 0.6694(4) 0.091(2) Uani 1 1 d .
H18A H 0.3592 -0.4558 0.6457 0.136 Uiso 1 1 calc R
H18B H 0.2015 -0.4098 0.6180 0.136 Uiso 1 1 calc R
H18C H 0.2058 -0.4408 0.7098 0.136 Uiso 1 1 calc R
C19 C 0.9453(7) 0.2806(4) 1.0706(3) 0.0543(13) Uani 1 1 d .
H19A H 0.9540 0.2503 1.1211 0.065 Uiso 1 1 calc R
H19B H 0.8987 0.3508 1.0948 0.065 Uiso 1 1 calc R
C20 C 1.1191(7) 0.3071(5) 1.0402(4) 0.0702(16) Uani 1 1 d .
H20A H 1.1889 0.3606 1.0942 0.084 Uiso 1 1 calc R
H20B H 1.1678 0.2375 1.0207 0.084 Uiso 1 1 calc R
C21 C 1.1313(8) 0.3554(5) 0.9636(4) 0.0738(16) Uani 1 1 d .
H21A H 1.0810 0.4244 0.9824 0.089 Uiso 1 1 calc R
H21B H 1.0641 0.3014 0.9090 0.089 Uiso 1 1 calc R
C22 C 1.3069(9) 0.3832(6) 0.9365(5) 0.109(3) Uani 1 1 d .
H22A H 1.3806 0.4240 0.9917 0.164 Uiso 1 1 calc R
H22B H 1.3059 0.4295 0.8976 0.164 Uiso 1 1 calc R
H22C H 1.3473 0.3138 0.9026 0.164 Uiso 1 1 calc R
N1 N 0.3307(4) 0.1986(3) 0.6137(2) 0.0370(8) Uani 1 1 d .
N2 N 0.2171(4) 0.0430(3) 0.6331(2) 0.0355(8) Uani 1 1 d .
N3 N 0.8274(5) 0.1980(3) 0.9947(2) 0.0428(9) Uani 1 1 d .
N4 N 0.7099(5) 0.0422(3) 0.8903(2) 0.0399(8) Uani 1 1 d .
S1 S -0.01140(16) -0.28883(9) 0.51963(8) 0.0469(3) Uani 1 1 d .
S2 S 0.48703(17) -0.29028(10) 0.82243(8) 0.0534(3) 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
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'
C C 0.0033 0.0016 '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'
S S 0.1246 0.1234 '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'
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
C1 Pd1 C1 180.00(18) 2_656 .
C1 Pd1 Cl1 90.29(11) 2_656 .
C1 Pd1 Cl1 89.71(11) . .
C1 Pd1 Cl1 89.71(11) 2_656 2_656
C1 Pd1 Cl1 90.29(11) . 2_656
Cl1 Pd1 Cl1 180.0 . 2_656
C12 Pd2 C12 180.00(19) . 2_757
C12 Pd2 Cl2 90.23(11) . 2_757
C12 Pd2 Cl2 89.77(11) 2_757 2_757
C12 Pd2 Cl2 89.77(11) . .
C12 Pd2 Cl2 90.23(11) 2_757 .
Cl2 Pd2 Cl2 180.0 2_757 .
N2 C1 N1 105.3(3) . .
N2 C1 Pd1 127.2(3) . .
N1 C1 Pd1 127.5(3) . .
C3 C2 N1 107.0(4) . .
C3 C2 H2 126.5 . .
N1 C2 H2 126.5 . .
C2 C3 N2 106.7(4) . .
C2 C3 H3 126.7 . .
N2 C3 H3 126.7 . .
N2 C4 C5 110.9(3) . .
N2 C4 H4A 109.5 . .
C5 C4 H4A 109.5 . .
N2 C4 H4B 109.5 . .
C5 C4 H4B 109.5 . .
H4A C4 H4B 108.1 . .
C4 C5 S1 112.4(3) . .
C4 C5 H5A 109.1 . .
S1 C5 H5A 109.1 . .
C4 C5 H5B 109.1 . .
S1 C5 H5B 109.1 . .
H5A C5 H5B 107.9 . .
C7 C6 S1 109.1(3) . .
C7 C6 H6A 109.9 . .
S1 C6 H6A 109.9 . .
C7 C6 H6B 109.9 . .
S1 C6 H6B 109.9 . .
H6A C6 H6B 108.3 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C9 112.7(4) . .
N1 C8 H8A 109.0 . .
C9 C8 H8A 109.0 . .
N1 C8 H8B 109.0 . .
C9 C8 H8B 109.0 . .
H8A C8 H8B 107.8 . .
C10 C9 C8 115.7(4) . .
C10 C9 H9A 108.4 . .
C8 C9 H9A 108.4 . .
C10 C9 H9B 108.4 . .
C8 C9 H9B 108.4 . .
H9A C9 H9B 107.4 . .
C9 C10 C11 113.0(5) . .
C9 C10 H10A 109.0 . .
C11 C10 H10A 109.0 . .
C9 C10 H10B 109.0 . .
C11 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N3 C12 N4 105.2(4) . .
N3 C12 Pd2 127.8(3) . .
N4 C12 Pd2 127.0(3) . .
C14 C13 N3 106.2(4) . .
C14 C13 H13 126.9 . .
N3 C13 H13 126.9 . .
C13 C14 N4 107.2(4) . .
C13 C14 H14 126.4 . .
N4 C14 H14 126.4 . .
N4 C15 C16 111.2(3) . .
N4 C15 H15A 109.4 . .
C16 C15 H15A 109.4 . .
N4 C15 H15B 109.4 . .
C16 C15 H15B 109.4 . .
H15A C15 H15B 108.0 . .
C15 C16 S2 112.5(3) . .
C15 C16 H16A 109.1 . .
S2 C16 H16A 109.1 . .
C15 C16 H16B 109.1 . .
S2 C16 H16B 109.1 . .
H16A C16 H16B 107.8 . .
C18 C17 S2 108.5(4) . .
C18 C17 H17A 110.0 . .
S2 C17 H17A 110.0 . .
C18 C17 H17B 110.0 . .
S2 C17 H17B 110.0 . .
H17A C17 H17B 108.4 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
N3 C19 C20 113.3(4) . .
N3 C19 H19A 108.9 . .
C20 C19 H19A 108.9 . .
N3 C19 H19B 108.9 . .
C20 C19 H19B 108.9 . .
H19A C19 H19B 107.7 . .
C21 C20 C19 116.7(5) . .
C21 C20 H20A 108.1 . .
C19 C20 H20A 108.1 . .
C21 C20 H20B 108.1 . .
C19 C20 H20B 108.1 . .
H20A C20 H20B 107.3 . .
C20 C21 C22 115.3(6) . .
C20 C21 H21A 108.5 . .
C22 C21 H21A 108.5 . .
C20 C21 H21B 108.5 . .
C22 C21 H21B 108.5 . .
H21A C21 H21B 107.5 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C1 N1 C2 110.3(3) . .
C1 N1 C8 123.6(3) . .
C2 N1 C8 126.1(3) . .
C1 N2 C3 110.8(3) . .
C1 N2 C4 123.9(3) . .
C3 N2 C4 125.2(4) . .
C12 N3 C13 111.3(3) . .
C12 N3 C19 124.0(4) . .
C13 N3 C19 124.7(4) . .
C12 N4 C14 110.2(3) . .
C12 N4 C15 124.0(4) . .
C14 N4 C15 125.7(4) . .
C5 S1 C6 100.50(19) . .
C16 S2 C17 100.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.025(4) 2_656
Pd1 C1 2.025(4) .
Pd1 Cl1 2.3094(10) .
Pd1 Cl1 2.3094(10) 2_656
Pd2 C12 2.030(4) .
Pd2 C12 2.030(4) 2_757
Pd2 Cl2 2.3083(10) 2_757
Pd2 Cl2 2.3083(10) .
C1 N2 1.349(5) .
C1 N1 1.351(5) .
C2 C3 1.341(6) .
C2 N1 1.392(5) .
C2 H2 0.9300 .
C3 N2 1.387(5) .
C3 H3 0.9300 .
C4 N2 1.451(5) .
C4 C5 1.523(6) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 S1 1.806(4) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.513(6) .
C6 S1 1.811(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 N1 1.449(5) .
C8 C9 1.515(7) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.491(6) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.544(8) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 N3 1.344(5) .
C12 N4 1.349(5) .
C13 C14 1.341(6) .
C13 N3 1.386(6) .
C13 H13 0.9300 .
C14 N4 1.393(6) .
C14 H14 0.9300 .
C15 N4 1.452(5) .
C15 C16 1.519(6) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 S2 1.804(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.526(7) .
C17 S2 1.810(5) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 N3 1.473(5) .
C19 C20 1.491(8) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.479(8) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.488(9) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
