#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:05:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178710 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/21/4082180.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_4082180
loop_
_publ_author_name
'Tato, Francisco'
'Garc\?ía-Dom\?ínguez, Andrés'
'Cárdenas, Diego J.'
_publ_section_title
;
 Palladium-Catalyzed Acetoxylation of Arenes by Novel Sulfinyl
 N-Heterocyclic Carbene Ligand Complexes
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              7487
_journal_paper_doi               10.1021/om400981x
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C34 H48 Cl4 N4 O6 Pd2 S2'
_chemical_formula_weight         1027.48
_chemical_name_common            tBuPd
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.1650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4303(3)
_cell_length_b                   11.8200(2)
_cell_length_c                   19.4801(3)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      27.1237
_cell_measurement_theta_min      2.7963
_cell_volume                     4403.70(12)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30939
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.627
_refine_diff_density_min         -0.417
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0889P)²+6.6868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1304
_reflns_number_gt                3274
_reflns_number_total             4018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400981x_si_002.cif
_cod_data_source_block           I
_cod_database_code               4082180
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 -0.0626(2) 0.7921(4) 0.59617(19) 0.0466(9) Uani d . 1
C C2 -0.0474(3) 0.6330(4) 0.6588(3) 0.0647(13) Uani d . 1
H H2 -0.0325 0.5609 0.6736 0.078 Uiso calc R 1
C C3 -0.0871(3) 0.7008(5) 0.6883(2) 0.0657(13) Uani d . 1
H H3 -0.1057 0.6847 0.7281 0.079 Uiso calc R 1
C C4 -0.1417(3) 0.8951(4) 0.6688(3) 0.0604(12) Uani d . 1
C C5 -0.1121(5) 0.9315(7) 0.7424(4) 0.113(2) Uani d . 1
H H5A -0.1168 0.8709 0.7741 0.17 Uiso calc R 1
H H5B -0.137 0.9967 0.7543 0.17 Uiso calc R 1
H H5C -0.0635 0.95 0.7456 0.17 Uiso calc R 1
C C6 -0.2142(3) 0.8457(8) 0.6689(5) 0.136(4) Uani d . 1
H H6A -0.2328 0.8167 0.6234 0.203 Uiso calc R 1
H H6B -0.2446 0.9037 0.6809 0.203 Uiso calc R 1
H H6C -0.2109 0.7855 0.7024 0.203 Uiso calc R 1
C C7 -0.1440(5) 0.9944(7) 0.6212(4) 0.137(4) Uani d . 1
H H7A -0.0972 1.0162 0.6175 0.206 Uiso calc R 1
H H7B -0.1671 1.0564 0.6395 0.206 Uiso calc R 1
H H7C -0.1692 0.9745 0.5759 0.206 Uiso calc R 1
C C8 0.0133(2) 0.6469(4) 0.5558(2) 0.0577(11) Uani d . 1
H H8A -0.0031 0.6733 0.5086 0.069 Uiso calc R 1
H H8B 0.0127 0.5648 0.5556 0.069 Uiso calc R 1
C C9 0.1404(3) 0.6386(5) 0.5189(3) 0.0670(13) Uani d . 1
C C10 0.1562(3) 0.5253(5) 0.5146(3) 0.0674(13) Uani d . 1
H H10 0.145 0.4739 0.5471 0.081 Uiso calc R 1
C C11 0.1890(3) 0.4898(5) 0.4609(3) 0.0703(13) Uani d . 1
H H11 0.2002 0.4137 0.4577 0.084 Uiso calc R 1
C C12 0.2053(3) 0.5629(6) 0.4128(3) 0.0762(15) Uani d . 1
C C13 0.1877(4) 0.6732(6) 0.4169(4) 0.114(3) Uani d . 1
H H13 0.1976 0.7231 0.3831 0.137 Uiso calc R 1
C C14 0.1552(5) 0.7146(6) 0.4703(4) 0.114(2) Uani d . 1
H H14 0.144 0.7909 0.4728 0.137 Uiso calc R 1
C C15 0.2427(4) 0.5257(7) 0.3555(3) 0.109(2) Uani d . 1
H H15A 0.2656 0.4548 0.3678 0.164 Uiso calc R 1
H H15B 0.2768 0.5816 0.3489 0.164 Uiso calc R 1
H H15C 0.2096 0.517 0.313 0.164 Uiso calc R 1
C C16 0.0709(5) 0.6466(7) 0.1724(4) 0.098(2) Uani d . 1
C C17 0.0793(7) 0.7574(7) 0.2032(5) 0.156(4) Uani d . 1
H H17A 0.123 0.789 0.1961 0.234 Uiso calc R 1
H H17B 0.0789 0.7518 0.2523 0.234 Uiso calc R 1
H H17C 0.0417 0.8052 0.1817 0.234 Uiso calc R 1
Cl Cl1 0.04168(7) 0.98922(11) 0.57949(5) 0.0681(4) Uani d . 1
Cl Cl2 -0.14731(6) 0.79458(11) 0.45782(6) 0.0662(3) Uani d . 1
N N1 -0.03215(18) 0.6893(3) 0.60169(17) 0.0507(8) Uani d . 1
N N2 -0.09673(19) 0.8011(3) 0.64988(17) 0.0545(9) Uani d . 1
O O1 0.1262(2) 0.6334(4) 0.6509(2) 0.0853(11) Uani d . 1
O O3 0.0274(3) 0.6160(5) 0.1243(4) 0.130(2) Uani d . 1
O O4 0.1223(3) 0.5762(5) 0.2001(3) 0.1209(18) Uani d . 1
H H4 0.1196 0.5176 0.1772 0.181 Uiso calc R 1
Pd Pd1 -0.05492(16) 0.89309(3) 0.517957(15) 0.04649(15) Uani d . 1
S S1 0.10194(8) 0.69771(12) 0.58690(8) 0.0742(4) Uani d . 1
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'
S S 0.1246 0.1234 '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_site_symmetry_3
_geom_angle
N2 C1 N1 . 106.3(3)
N2 C1 Pd1 . 132.4(3)
N1 C1 Pd1 . 121.2(3)
C3 C2 N1 . 106.7(4)
C3 C2 H2 . 126.7
N1 C2 H2 . 126.7
C2 C3 N2 . 108.4(4)
C2 C3 H3 . 125.8
N2 C3 H3 . 125.8
C7 C4 N2 . 112.6(4)
C7 C4 C5 . 109.4(6)
N2 C4 C5 . 107.6(5)
C7 C4 C6 . 112.1(6)
N2 C4 C6 . 107.1(5)
C5 C4 C6 . 107.8(6)
C4 C5 H5A . 109.5
C4 C5 H5B . 109.5
H5A C5 H5B . 109.5
C4 C5 H5C . 109.5
H5A C5 H5C . 109.5
H5B C5 H5C . 109.5
C4 C6 H6A . 109.5
C4 C6 H6B . 109.5
H6A C6 H6B . 109.5
C4 C6 H6C . 109.5
H6A C6 H6C . 109.5
H6B C6 H6C . 109.5
C4 C7 H7A . 109.5
C4 C7 H7B . 109.5
H7A C7 H7B . 109.5
C4 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
N1 C8 S1 . 108.9(3)
N1 C8 H8A . 109.9
S1 C8 H8A . 109.9
N1 C8 H8B . 109.9
S1 C8 H8B . 109.9
H8A C8 H8B . 108.3
C14 C9 C10 . 121.2(5)
C14 C9 S1 . 115.1(5)
C10 C9 S1 . 123.7(4)
C9 C10 C11 . 118.5(5)
C9 C10 H10 . 120.8
C11 C10 H10 . 120.8
C12 C11 C10 . 121.7(5)
C12 C11 H11 . 119.1
C10 C11 H11 . 119.1
C11 C12 C13 . 118.8(5)
C11 C12 C15 . 122.1(6)
C13 C12 C15 . 119.1(6)
C12 C13 C14 . 122.3(6)
C12 C13 H13 . 118.9
C14 C13 H13 . 118.9
C9 C14 C13 . 117.4(6)
C9 C14 H14 . 121.3
C13 C14 H14 . 121.3
C12 C15 H15A . 109.5
C12 C15 H15B . 109.5
H15A C15 H15B . 109.5
C12 C15 H15C . 109.5
H15A C15 H15C . 109.5
H15B C15 H15C . 109.5
O3 C16 O4 . 120.0(8)
O3 C16 C17 . 127.7(9)
O4 C16 C17 . 112.1(8)
C16 C17 H17A . 109.5
C16 C17 H17B . 109.5
H17A C17 H17B . 109.5
C16 C17 H17C . 109.5
H17A C17 H17C . 109.5
H17B C17 H17C . 109.5
Pd1 Cl1 Pd1 5_576 93.70(4)
C1 N1 C2 . 110.3(4)
C1 N1 C8 . 124.6(3)
C2 N1 C8 . 125.0(4)
C1 N2 C3 . 108.3(4)
C1 N2 C4 . 130.0(4)
C3 N2 C4 . 121.7(4)
C16 O4 H4 . 109.5
C1 Pd1 Cl2 . 85.85(12)
C1 Pd1 Cl1 . 93.54(12)
Cl2 Pd1 Cl1 . 178.33(5)
C1 Pd1 Cl1 5_576 177.33(12)
Cl2 Pd1 Cl1 5_576 94.25(4)
Cl1 Pd1 Cl1 5_576 86.30(4)
O1 S1 C9 . 108.5(2)
O1 S1 C8 . 104.7(2)
C9 S1 C8 . 96.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N2 . 1.339(5)
C1 N1 . 1.347(5)
C1 Pd1 . 1.962(4)
C2 C3 . 1.314(7)
C2 N1 . 1.372(6)
C2 H2 . 0.93
C3 N2 . 1.398(6)
C3 H3 . 0.93
C4 C7 . 1.492(9)
C4 N2 . 1.500(6)
C4 C5 . 1.510(8)
C4 C6 . 1.525(8)
C5 H5A . 0.96
C5 H5B . 0.96
C5 H5C . 0.96
C6 H6A . 0.96
C6 H6B . 0.96
C6 H6C . 0.96
C7 H7A . 0.96
C7 H7B . 0.96
C7 H7C . 0.96
C8 N1 . 1.451(5)
C8 S1 . 1.824(5)
C8 H8A . 0.97
C8 H8B . 0.97
C9 C14 . 1.372(9)
C9 C10 . 1.380(7)
C9 S1 . 1.775(5)
C10 C11 . 1.383(7)
C10 H10 . 0.93
C11 C12 . 1.351(8)
C11 H11 . 0.93
C12 C13 . 1.354(10)
C12 C15 . 1.502(8)
C13 C14 . 1.397(10)
C13 H13 . 0.93
C14 H14 . 0.93
C15 H15A . 0.96
C15 H15B . 0.96
C15 H15C . 0.96
C16 O3 . 1.202(9)
C16 O4 . 1.338(10)
C16 C17 . 1.438(10)
C17 H17A . 0.96
C17 H17B . 0.96
C17 H17C . 0.96
Cl1 Pd1 . 2.3360(11)
Cl1 Pd1 5_576 2.4036(11)
Cl2 Pd1 . 2.2822(11)
O1 S1 . 1.465(5)
O4 H4 . 0.82
Pd1 Cl1 5_576 2.4035(11)
