Supplementary Material (ESI) for Dalton Transactions
This journal is © The Royal Society of Chemistry 2003


data_global

_publ_contact_author_email       MATS.TILSET@KJEMI.UIO.NO

_publ_contact_author_name        'Prof Mats Tilset'
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_publ_contact_author_address     
;
Dept. of Chemistry
University of Oslo
P.O.Box 1033 Blindern
Oslo
0315
NORWAY
;

_publ_section_title              
;
Synthesis and Characterization of Palladium(II)
Complexes with a Novel Chelating Iminocarbene Ligand
;

loop_
_publ_author_name
'Mats Tilset'
'Ajaib Dhindsa'
'Morten Froseth'
'Hilde Roise'

data_morten2
_database_code_CSD               215694

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C20 H29 Cl4 N3 Pd'
_chemical_formula_weight         559.66
_chemical_melting_point          ?
_chemical_compound_source        ?

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   13.325(3)
_cell_length_b                   14.218(3)
_cell_length_c                   25.334(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4799.6(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2272
_exptl_absorpt_coefficient_mu    1.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'SMART CCD Area Detector'
_diffrn_measurement_method       \w-scan
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            52969
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         28.79
_reflns_number_total             5839
_reflns_number_observed          4035
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 15 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses 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 observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+48.2926P] 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    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5824
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_obs          0.0538
_refine_ls_wR_factor_all         0.1568
_refine_ls_wR_factor_obs         0.1228
_refine_ls_goodness_of_fit_all   1.197
_refine_ls_goodness_of_fit_obs   1.150
_refine_ls_restrained_S_all      1.212
_refine_ls_restrained_S_obs      1.150
_refine_ls_shift/esd_max         0.004
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Pd1 Pd 0.65893(3) 0.02335(3) 0.35885(2) 0.01900(13) Uani 1 d . .
Cl1 Cl 0.57295(12) 0.13910(10) 0.40841(6) 0.0256(3) Uani 1 d . .
Cl2 Cl 0.55749(13) 0.05175(13) 0.28741(7) 0.0342(4) Uani 1 d . .
Cl3 Cl 0.7498(2) 0.2140(2) 0.15796(8) 0.0507(5) Uani 1 d . .
Cl4 Cl 0.9012(2) 0.3246(3) 0.2156(2) 0.0931(11) Uani 1 d . .
N1 N 0.7507(4) -0.0148(3) 0.4216(2) 0.0188(10) Uani 1 d . .
N2 N 0.7630(4) -0.1516(4) 0.3391(2) 0.0235(11) Uani 1 d . .
N3 N 0.7853(4) -0.0634(4) 0.2709(2) 0.0283(12) Uani 1 d . .
C1 C 0.7965(4) 0.0608(4) 0.4524(2) 0.0194(12) Uani 1 d . .
C2 C 0.7521(5) 0.0882(4) 0.5006(2) 0.0201(12) Uani 1 d . .
C3 C 0.7973(5) 0.1618(5) 0.5277(2) 0.0258(13) Uani 1 d . .
H3 H 0.7694(5) 0.1824(5) 0.5593(2) 0.031 Uiso 1 calc R .
C4 C 0.8833(5) 0.2052(5) 0.5086(3) 0.0267(14) Uani 1 d . .
H4 H 0.9129(5) 0.2537(5) 0.5277(3) 0.032 Uiso 1 calc R .
C5 C 0.9252(5) 0.1770(4) 0.4614(2) 0.0245(13) Uani 1 d . .
H5 H 0.9821(5) 0.2072(4) 0.4487(2) 0.029 Uiso 1 calc R .
C6 C 0.8825(5) 0.1027(4) 0.4323(2) 0.0214(12) Uani 1 d . .
C7 C 0.9327(5) 0.0721(5) 0.3808(3) 0.0263(13) Uani 1 d . .
H7 H 0.8958(5) 0.0176(5) 0.3673(3) 0.032 Uiso 1 calc R .
C8 C 1.0421(6) 0.0412(7) 0.3902(3) 0.052(2) Uani 1 d . .
H8A H 1.0792(13) 0.0924(16) 0.4053(23) 0.079 Uiso 1 calc R .
H8B H 1.0719(16) 0.0234(43) 0.3572(5) 0.079 Uiso 1 calc R .
H8C H 1.0432(7) -0.0115(29) 0.4139(20) 0.079 Uiso 1 calc R .
C9 C 0.9284(7) 0.1486(6) 0.3390(3) 0.049(2) Uani 1 d . .
H9A H 0.8597(8) 0.1656(31) 0.3326(18) 0.074 Uiso 1 calc R .
H9B H 0.9579(44) 0.1258(17) 0.3069(8) 0.074 Uiso 1 calc R .
H9C H 0.9648(40) 0.2028(18) 0.3510(11) 0.074 Uiso 1 calc R .
C10 C 0.6603(5) 0.0393(4) 0.5239(2) 0.0230(12) Uani 1 d . .
H10 H 0.6286(5) 0.0026(4) 0.4958(2) 0.028 Uiso 1 calc R .
C11 C 0.6907(5) -0.0292(6) 0.5683(3) 0.037(2) Uani 1 d . .
H11A H 0.7401(30) -0.0725(25) 0.5552(7) 0.056 Uiso 1 calc R .
H11B H 0.6327(9) -0.0635(28) 0.5800(15) 0.056 Uiso 1 calc R .
H11C H 0.7182(37) 0.0056(6) 0.5974(9) 0.056 Uiso 1 calc R .
C12 C 0.5820(5) 0.1083(5) 0.5456(3) 0.033(2) Uani 1 d . .
H12A H 0.6095(14) 0.1413(26) 0.5753(13) 0.050 Uiso 1 calc R .
H12B H 0.5233(16) 0.0742(6) 0.5564(19) 0.050 Uiso 1 calc R .
H12C H 0.5641(29) 0.1526(23) 0.5185(7) 0.050 Uiso 1 calc R .
C13 C 0.8539(5) -0.1320(5) 0.4692(3) 0.0301(15) Uani 1 d . .
H13A H 0.8742(28) -0.0798(8) 0.4907(13) 0.045 Uiso 1 calc R .
H13B H 0.9113(16) -0.1572(31) 0.4512(3) 0.045 Uiso 1 calc R .
H13C H 0.8248(13) -0.1798(25) 0.4911(13) 0.045 Uiso 1 calc R .
C14 C 0.7781(5) -0.0997(4) 0.4295(2) 0.0217(12) Uani 1 d . .
C15 C 0.7358(5) -0.1748(4) 0.3930(2) 0.0268(14) Uani 1 d . .
H15A H 0.7629(5) -0.2358(4) 0.4024(2) 0.032 Uiso 1 calc R .
H15B H 0.6634(5) -0.1773(4) 0.3964(2) 0.032 Uiso 1 calc R .
C16 C 0.8291(5) -0.2000(5) 0.3067(3) 0.034(2) Uani 1 d . .
H16 H 0.8588(5) -0.2581(5) 0.3131(3) 0.040 Uiso 1 calc R .
C17 C 0.8411(6) -0.1450(5) 0.2640(3) 0.036(2) Uani 1 d . .
H17 H 0.8803(6) -0.1592(5) 0.2347(3) 0.043 Uiso 1 calc R .
C18 C 0.7817(5) 0.0130(5) 0.2326(3) 0.035(2) Uani 1 d . .
H18A H 0.7326(29) -0.0012(18) 0.2060(12) 0.053 Uiso 1 calc R .
H18B H 0.8463(12) 0.0201(25) 0.2164(15) 0.053 Uiso 1 calc R .
H18C H 0.7636(39) 0.0704(9) 0.2501(5) 0.053 Uiso 1 calc R .
C19 C 0.7367(4) -0.0678(4) 0.3180(2) 0.0216(12) Uani 1 d . .
C20 C 0.8787(7) 0.2380(8) 0.1690(4) 0.064(3) Uani 1 d . .
H20A H 0.9114(7) 0.1805(8) 0.1803(4) 0.077 Uiso 1 calc R .
H20B H 0.9090(7) 0.2570(8) 0.1359(4) 0.077 Uiso 1 calc R .

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 0.0178(2) 0.0177(2) 0.0215(2) -0.0002(2) -0.0038(2) 0.0005(2)
Cl1 0.0256(7) 0.0220(7) 0.0292(8) -0.0005(6) -0.0013(6) 0.0045(6)
Cl2 0.0308(8) 0.0423(9) 0.0295(8) -0.0030(7) -0.0130(7) 0.0095(7)
Cl3 0.0669(14) 0.0490(12) 0.0362(9) 0.0022(9) 0.0038(10) 0.0073(11)
Cl4 0.0464(15) 0.100(2) 0.133(3) -0.037(2) 0.007(2) 0.0075(15)
N1 0.016(2) 0.021(2) 0.020(2) -0.002(2) -0.003(2) 0.002(2)
N2 0.029(3) 0.021(3) 0.020(2) -0.003(2) -0.005(2) 0.003(2)
N3 0.027(3) 0.036(3) 0.022(3) 0.002(2) 0.000(2) -0.001(2)
C1 0.019(3) 0.019(3) 0.020(3) 0.000(2) -0.006(2) 0.001(2)
C2 0.023(3) 0.019(3) 0.018(3) 0.000(2) -0.002(2) 0.003(2)
C3 0.029(3) 0.029(3) 0.020(3) -0.006(3) 0.003(3) 0.001(3)
C4 0.029(3) 0.025(3) 0.027(3) -0.007(3) -0.007(3) -0.005(3)
C5 0.021(3) 0.025(3) 0.027(3) -0.002(3) 0.000(3) -0.002(2)
C6 0.021(3) 0.022(3) 0.022(3) -0.002(2) -0.001(2) 0.002(2)
C7 0.023(3) 0.030(3) 0.026(3) -0.007(3) -0.001(3) -0.005(3)
C8 0.031(4) 0.079(7) 0.047(5) -0.007(4) 0.001(4) 0.020(4)
C9 0.069(6) 0.048(5) 0.030(4) -0.001(4) 0.018(4) 0.013(4)
C10 0.021(3) 0.026(3) 0.022(3) 0.001(2) 0.000(2) 0.000(3)
C11 0.028(3) 0.043(4) 0.041(4) 0.014(4) 0.006(3) 0.001(3)
C12 0.029(4) 0.037(4) 0.033(4) -0.004(3) 0.005(3) 0.003(3)
C13 0.037(4) 0.023(3) 0.031(3) -0.004(3) -0.012(3) 0.004(3)
C14 0.023(3) 0.022(3) 0.021(3) 0.001(2) -0.002(2) -0.002(2)
C15 0.034(4) 0.018(3) 0.028(3) 0.003(2) -0.002(3) 0.001(3)
C16 0.036(4) 0.036(4) 0.029(3) -0.010(3) -0.006(3) 0.012(3)
C17 0.032(4) 0.051(4) 0.026(3) -0.011(3) -0.001(3) 0.012(4)
C18 0.030(4) 0.046(4) 0.029(3) 0.009(3) -0.003(3) -0.002(3)
C19 0.017(3) 0.025(3) 0.023(3) 0.002(2) -0.005(2) -0.004(2)
C20 0.057(6) 0.079(7) 0.058(6) -0.002(5) 0.009(5) 0.030(5)

_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 C19 1.956(6) . ?
Pd1 N1 2.077(5) . ?
Pd1 Cl2 2.295(2) . ?
Pd1 Cl1 2.366(2) . ?
Cl3 C20 1.773(11) . ?
Cl4 C20 1.732(11) . ?
N1 C14 1.278(8) . ?
N1 C1 1.463(7) . ?
N2 C19 1.352(8) . ?
N2 C16 1.387(8) . ?
N2 C15 1.451(8) . ?
N3 C19 1.359(8) . ?
N3 C17 1.388(9) . ?
N3 C18 1.458(9) . ?
C1 C6 1.389(8) . ?
C1 C2 1.411(8) . ?
C2 C3 1.388(9) . ?
C2 C10 1.525(9) . ?
C3 C4 1.390(9) . ?
C4 C5 1.378(9) . ?
C5 C6 1.408(8) . ?
C6 C7 1.528(8) . ?
C7 C9 1.520(10) . ?
C7 C8 1.540(10) . ?
C10 C12 1.534(9) . ?
C10 C11 1.542(9) . ?
C13 C14 1.497(9) . ?
C14 C15 1.521(8) . ?
C16 C17 1.343(10) . ?

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
C19 Pd1 N1 85.4(2) . . ?
C19 Pd1 Cl2 90.7(2) . . ?
N1 Pd1 Cl2 174.94(14) . . ?
C19 Pd1 Cl1 176.8(2) . . ?
N1 Pd1 Cl1 93.46(14) . . ?
Cl2 Pd1 Cl1 90.62(6) . . ?
C14 N1 C1 119.4(5) . . ?
C14 N1 Pd1 122.4(4) . . ?
C1 N1 Pd1 117.5(4) . . ?
C19 N2 C16 111.6(5) . . ?
C19 N2 C15 120.5(5) . . ?
C16 N2 C15 127.1(6) . . ?
C19 N3 C17 109.1(6) . . ?
C19 N3 C18 127.1(6) . . ?
C17 N3 C18 123.9(6) . . ?
C6 C1 C2 123.1(5) . . ?
C6 C1 N1 117.6(5) . . ?
C2 C1 N1 119.3(5) . . ?
C3 C2 C1 116.9(6) . . ?
C3 C2 C10 120.0(5) . . ?
C1 C2 C10 123.0(5) . . ?
C2 C3 C4 121.4(6) . . ?
C5 C4 C3 120.4(6) . . ?
C4 C5 C6 120.7(6) . . ?
C1 C6 C5 117.5(6) . . ?
C1 C6 C7 123.6(5) . . ?
C5 C6 C7 119.0(6) . . ?
C9 C7 C6 112.0(6) . . ?
C9 C7 C8 110.4(7) . . ?
C6 C7 C8 111.3(6) . . ?
C2 C10 C12 113.1(5) . . ?
C2 C10 C11 111.1(5) . . ?
C12 C10 C11 108.8(5) . . ?
N1 C14 C13 126.1(6) . . ?
N1 C14 C15 117.5(5) . . ?
C13 C14 C15 116.3(5) . . ?
N2 C15 C14 108.7(5) . . ?
C17 C16 N2 105.3(6) . . ?
C16 C17 N3 108.8(6) . . ?
N2 C19 N3 105.3(5) . . ?
N2 C19 Pd1 120.8(4) . . ?
N3 C19 Pd1 133.4(5) . . ?
Cl4 C20 Cl3 114.4(5) . . ?

_refine_diff_density_max         3.520
_refine_diff_density_min         -1.538
_refine_diff_density_rms         0.154