# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Braunstein, Pierre'

_publ_contact_author_name        'Braunstein, Pierre'
_publ_contact_author_email       braunst@chimie.u-strasbg.fr

_publ_section_title              
;
Synthesis of N,N\^a-bis(thioether)-
functionalized imidazolium salts: their reactivity
towards Ag and Pd complexes and first S,CNHC,S free carbene
;

# Attachment '- final_CF100216.cif'

data_CF_100216
_database_code_depnum_ccdc_archive 'CCDC 781531'
#TrackingRef '- final_CF100216.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H22 Cl2 N2 Pd S, C H2 Cl2'
_chemical_formula_sum            'C17 H24 Cl4 N2 Pd S'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         536.64

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'
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.778(1)
_cell_length_b                   11.845(1)
_cell_length_c                   14.879(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.886(4)
_cell_angle_gamma                90.00
_cell_volume                     2186.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    31920
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    1.437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12428
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         29.12
_reflns_number_total             5857
_reflns_number_gt                3740
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  PLATON

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5857
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Pd1 Pd 0.14549(2) 0.17307(3) 0.929993(18) 0.03042(12) Uani 1 1 d . . .
C1 C 0.2509(3) 0.2557(3) 1.0264(2) 0.0314(9) Uani 1 1 d . . .
C2 C 0.3880(4) 0.3599(4) 1.1045(3) 0.0424(11) Uani 1 1 d . . .
H2 H 0.4497 0.4045 1.1174 0.051 Uiso 1 1 calc R . .
C3 C 0.3347(4) 0.3238(3) 1.1654(3) 0.0410(10) Uani 1 1 d . . .
H3 H 0.3514 0.3389 1.2285 0.049 Uiso 1 1 calc R . .
C4 C 0.1594(4) 0.2213(4) 1.1526(3) 0.0451(11) Uani 1 1 d . . .
H4A H 0.1751 0.2347 1.2188 0.054 Uiso 1 1 calc R . .
H4B H 0.1491 0.1408 1.1422 0.054 Uiso 1 1 calc R . .
C5 C 0.0570(4) 0.2833(4) 1.1058(3) 0.0505(12) Uani 1 1 d . . .
H5A H 0.0706 0.3639 1.1104 0.061 Uiso 1 1 calc R . .
H5B H 0.0016 0.2667 1.1385 0.061 Uiso 1 1 calc R . .
C6 C -0.0802(3) 0.1282(4) 0.9969(3) 0.0462(11) Uani 1 1 d . . .
H6A H -0.0878 0.0779 0.9443 0.055 Uiso 1 1 calc R . .
H6B H -0.0473 0.0859 1.0524 0.055 Uiso 1 1 calc R . .
C7 C -0.1894(4) 0.1687(4) 1.0032(4) 0.0664(16) Uani 1 1 d . . .
H7A H -0.1821 0.2180 1.0555 0.100 Uiso 1 1 calc R . .
H7B H -0.2333 0.1051 1.0103 0.100 Uiso 1 1 calc R . .
H7C H -0.2228 0.2088 0.9477 0.100 Uiso 1 1 calc R . .
C8 C 0.3633(3) 0.3532(3) 0.9335(3) 0.0342(9) Uani 1 1 d . . .
C9 C 0.2959(4) 0.4302(4) 0.8756(3) 0.0398(10) Uani 1 1 d . . .
C10 C 0.3283(4) 0.4628(4) 0.7959(3) 0.0489(12) Uani 1 1 d . . .
H10 H 0.2844 0.5120 0.7548 0.059 Uiso 1 1 calc R . .
C11 C 0.4215(4) 0.4257(4) 0.7754(3) 0.0502(12) Uani 1 1 d . . .
C12 C 0.4879(4) 0.3524(4) 0.8366(3) 0.0514(13) Uani 1 1 d . . .
H12 H 0.5520 0.3279 0.8240 0.062 Uiso 1 1 calc R . .
C13 C 0.4596(3) 0.3147(4) 0.9170(3) 0.0445(11) Uani 1 1 d . . .
C14 C 0.5320(4) 0.2344(5) 0.9808(3) 0.0590(14) Uani 1 1 d . . .
H14A H 0.5818 0.2010 0.9494 0.089 Uiso 1 1 calc R . .
H14B H 0.4894 0.1762 0.9996 0.089 Uiso 1 1 calc R . .
H14C H 0.5713 0.2745 1.0345 0.089 Uiso 1 1 calc R . .
C15 C 0.4538(5) 0.4656(5) 0.6885(4) 0.0761(17) Uani 1 1 d . . .
H15A H 0.4050 0.4348 0.6348 0.114 Uiso 1 1 calc R . .
H15B H 0.5258 0.4407 0.6903 0.114 Uiso 1 1 calc R . .
H15C H 0.4511 0.5466 0.6856 0.114 Uiso 1 1 calc R . .
C16 C 0.1939(4) 0.4753(4) 0.8957(3) 0.0531(12) Uani 1 1 d . . .
H16A H 0.1370 0.4212 0.8764 0.080 Uiso 1 1 calc R . .
H16B H 0.1743 0.5447 0.8626 0.080 Uiso 1 1 calc R . .
H16C H 0.2052 0.4889 0.9609 0.080 Uiso 1 1 calc R . .
C17 C 0.1711(4) 0.6408(4) 1.2369(3) 0.0550(12) Uani 1 1 d . . .
H17A H 0.1009 0.6764 1.2170 0.066 Uiso 1 1 calc R . .
H17B H 0.1685 0.5889 1.2867 0.066 Uiso 1 1 calc R . .
S1 S 0.00711(8) 0.24583(9) 0.98434(7) 0.0383(3) Uani 1 1 d . . .
Cl1 Cl 0.01672(8) 0.08693(10) 0.80844(7) 0.0457(3) Uani 1 1 d . . .
Cl2 Cl 0.28598(8) 0.08872(9) 0.88276(7) 0.0404(3) Uani 1 1 d . . .
Cl3 Cl 0.26929(14) 0.74376(13) 1.27675(10) 0.0801(4) Uani 1 1 d . . .
Cl4 Cl 0.20101(12) 0.56621(11) 1.14383(9) 0.0654(4) Uani 1 1 d . . .
N1 N 0.3351(3) 0.3190(3) 1.0180(2) 0.0311(7) Uani 1 1 d . . .
N2 N 0.2494(3) 0.2592(3) 1.11671(19) 0.0340(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pd1 0.03060(18) 0.0367(2) 0.02484(17) 0.00080(13) 0.00832(12) -0.00158(13)
C1 0.031(2) 0.036(2) 0.0272(19) 0.0000(17) 0.0081(15) 0.0099(18)
C2 0.042(2) 0.045(3) 0.033(2) -0.014(2) -0.0045(19) -0.001(2)
C3 0.046(2) 0.044(3) 0.030(2) -0.0082(19) 0.0021(18) 0.007(2)
C4 0.053(3) 0.058(3) 0.028(2) 0.001(2) 0.0156(19) -0.001(2)
C5 0.050(3) 0.062(3) 0.044(2) -0.002(2) 0.021(2) 0.011(2)
C6 0.042(2) 0.056(3) 0.045(2) 0.010(2) 0.0183(19) -0.001(2)
C7 0.046(3) 0.075(4) 0.088(4) 0.036(3) 0.035(3) 0.012(3)
C8 0.036(2) 0.034(2) 0.032(2) -0.0055(18) 0.0071(17) -0.0069(18)
C9 0.050(3) 0.035(2) 0.032(2) -0.0062(19) 0.0063(18) -0.008(2)
C10 0.061(3) 0.041(3) 0.039(2) -0.002(2) 0.002(2) -0.015(2)
C11 0.059(3) 0.051(3) 0.045(3) -0.012(2) 0.020(2) -0.028(2)
C12 0.039(2) 0.066(3) 0.054(3) -0.016(3) 0.021(2) -0.023(2)
C13 0.035(2) 0.055(3) 0.043(2) -0.012(2) 0.0102(19) -0.015(2)
C14 0.037(3) 0.082(4) 0.058(3) -0.005(3) 0.011(2) 0.006(3)
C15 0.100(5) 0.077(4) 0.062(3) -0.005(3) 0.041(3) -0.032(4)
C16 0.057(3) 0.051(3) 0.048(3) 0.010(2) 0.006(2) 0.014(2)
C17 0.064(3) 0.052(3) 0.049(3) 0.011(2) 0.013(2) 0.004(3)
S1 0.0335(5) 0.0445(6) 0.0389(5) 0.0084(5) 0.0129(4) 0.0065(5)
Cl1 0.0420(6) 0.0592(7) 0.0331(5) -0.0025(5) 0.0038(4) -0.0130(5)
Cl2 0.0436(6) 0.0422(6) 0.0417(5) -0.0097(5) 0.0228(4) -0.0057(5)
Cl3 0.0956(11) 0.0684(10) 0.0765(10) -0.0095(8) 0.0210(8) -0.0146(8)
Cl4 0.0894(10) 0.0468(7) 0.0621(8) -0.0003(6) 0.0226(7) 0.0161(7)
N1 0.0274(16) 0.0381(19) 0.0254(15) -0.0041(14) 0.0016(13) -0.0008(14)
N2 0.0407(19) 0.040(2) 0.0215(15) -0.0006(14) 0.0076(13) 0.0077(16)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 C1 1.976(4) . ?
Pd1 S1 2.2823(11) . ?
Pd1 Cl2 2.3066(10) . ?
Pd1 Cl1 2.3645(10) . ?
C1 N1 1.342(5) . ?
C1 N2 1.349(4) . ?
C2 C3 1.328(6) . ?
C2 N1 1.388(5) . ?
C2 H2 0.9300 . ?
C3 N2 1.385(5) . ?
C3 H3 0.9300 . ?
C4 N2 1.451(5) . ?
C4 C5 1.515(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 S1 1.821(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.500(6) . ?
C6 S1 1.822(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.389(6) . ?
C8 C9 1.400(6) . ?
C8 N1 1.446(5) . ?
C9 C10 1.401(6) . ?
C9 C16 1.504(6) . ?
C10 C11 1.371(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(7) . ?
C11 C15 1.524(6) . ?
C12 C13 1.404(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.497(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 Cl3 1.748(5) . ?
C17 Cl4 1.761(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
_geom_angle_publ_flag
C1 Pd1 S1 90.39(11) . . ?
C1 Pd1 Cl2 89.48(11) . . ?
S1 Pd1 Cl2 175.76(4) . . ?
C1 Pd1 Cl1 175.73(11) . . ?
S1 Pd1 Cl1 88.73(4) . . ?
Cl2 Pd1 Cl1 91.70(4) . . ?
N1 C1 N2 106.2(3) . . ?
N1 C1 Pd1 129.2(3) . . ?
N2 C1 Pd1 124.6(3) . . ?
C3 C2 N1 107.8(4) . . ?
C3 C2 H2 126.1 . . ?
N1 C2 H2 126.1 . . ?
C2 C3 N2 106.8(4) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
N2 C4 C5 110.7(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 113.3(3) . . ?
C4 C5 H5A 108.9 . . ?
S1 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
S1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 S1 111.3(3) . . ?
C7 C6 H6A 109.4 . . ?
S1 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
S1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
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 . . ?
C13 C8 C9 123.1(4) . . ?
C13 C8 N1 118.5(4) . . ?
C9 C8 N1 118.2(4) . . ?
C8 C9 C10 115.9(4) . . ?
C8 C9 C16 122.9(4) . . ?
C10 C9 C16 121.1(4) . . ?
C11 C10 C9 123.3(4) . . ?
C11 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C10 C11 C12 118.7(4) . . ?
C10 C11 C15 121.1(5) . . ?
C12 C11 C15 120.2(5) . . ?
C11 C12 C13 121.1(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 117.8(4) . . ?
C8 C13 C14 122.4(4) . . ?
C12 C13 C14 119.8(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Cl3 C17 Cl4 110.1(3) . . ?
Cl3 C17 H17A 109.6 . . ?
Cl4 C17 H17A 109.6 . . ?
Cl3 C17 H17B 109.6 . . ?
Cl4 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
C5 S1 C6 99.3(2) . . ?
C5 S1 Pd1 109.09(15) . . ?
C6 S1 Pd1 107.04(16) . . ?
C1 N1 C2 109.3(3) . . ?
C1 N1 C8 127.5(3) . . ?
C2 N1 C8 122.8(4) . . ?
C1 N2 C3 109.9(3) . . ?
C1 N2 C4 124.0(3) . . ?
C3 N2 C4 124.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.266
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.129