# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004


data_global

_journal_coden_Cambridge         182

_publ_section_title              
;
The Synthesis of a Di-N-Heterocyclic Carbene Amido
Complex of Palladium(II)
;
_publ_contact_author_name        'Richard E. Douthwaite'
_publ_contact_author_address     
;
Deparment of Chemistry
University of York
Heslington York YO10 4DD
;
_publ_contact_author_phone       ' 01904 434183 '
_publ_contact_author_fax         ' 01904 432516 '
_publ_contact_author_email       ' red4@york.ac.uk '

_publ_requested_journal          'Chemical Communications'

loop_
_publ_author_name
_publ_author_address

;
Douthwaite, Richard E.
;
;
Deparment of Chemistry
University of York
Heslington York YO10 4DD
;
;
Houghton, Jennifer
;
;
Deparment of Chemistry
University of York
Heslington York YO10 4DD
;
;
Benson M. Kariuki
;
;
School of Chemical Sciences
University of Birmingham
Edgbaston, Birmingham B15 2TT
;

data_red
_database_code_depnum_ccdc_archive 'CCDC 225003'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H31 Cl1 N5 Pd, Cl1'
_chemical_formula_sum            'C18 H31 Cl2 N5 Pd'
_chemical_formula_weight         494.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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   P21/c

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                   12.5628(15)
_cell_length_b                   10.3135(15)
_cell_length_c                   17.2307(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.159(7)
_cell_angle_gamma                90.00
_cell_volume                     2230.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1055
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      40.87

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    8.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.1234
_exptl_absorpt_correction_T_max  0.7148
_exptl_absorpt_process_details   'Sadabs in Saintplus'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4802
_diffrn_reflns_av_R_equivalents  0.1069
_diffrn_reflns_av_sigmaI/netI    0.1712
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         40.87
_reflns_number_total             1407
_reflns_number_gt                1055
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART v5.625 (Bruker)'
_computing_cell_refinement       'SAINT+ v6.22 (Bruker)'
_computing_data_reduction        'SAINT+ v6.22 (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
The crystal was very small in one dimension limiting the quantity
of the data that could be acquired. Insufficient intensity
was observed > 41 degrees resulting in a low data/parameter ratio.

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^)+(0.0000P)^2^+2.2224P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1407
_refine_ls_number_parameters     241
_refine_ls_number_restraints     177
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1820
_refine_ls_wR_factor_gt          0.1623
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_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
Cl1 Cl 0.7479(3) 0.7656(4) 0.2173(2) 0.0457(15) Uani 1 1 d . . .
Cl2 Cl 0.7584(3) 0.3744(4) 0.4728(2) 0.0511(15) Uani 1 1 d . . .
Pd1 Pd 0.76174(9) 0.72988(12) 0.35153(7) 0.0374(8) Uani 1 1 d . . .
N3 N 0.7669(9) 0.6774(13) 0.4668(7) 0.044(4) Uani 1 1 d U . .
H3A H 0.7523 0.5910 0.4649 0.052 Uiso 1 1 calc R . .
C1 C 0.6197(11) 0.6308(15) 0.3520(9) 0.039(4) Uani 1 1 d DU . .
N1 N 0.5680(9) 0.5306(11) 0.3176(7) 0.034(3) Uani 1 1 d DU . .
C2 C 0.4673(11) 0.5130(15) 0.3507(9) 0.042(4) Uani 1 1 d DU . .
H2 H 0.4160 0.4517 0.3363 0.050 Uiso 1 1 calc R . .
C3 C 0.4607(12) 0.6020(15) 0.4068(9) 0.046(4) Uani 1 1 d DU . .
H3 H 0.4036 0.6139 0.4388 0.055 Uiso 1 1 calc R . .
N2 N 0.5535(9) 0.6728(12) 0.4087(7) 0.038(3) Uani 1 1 d DU . .
C4 C 0.5850(12) 0.7710(14) 0.4636(9) 0.045(4) Uani 1 1 d DU . .
H4A H 0.5253 0.7913 0.4956 0.054 Uiso 1 1 calc R . .
H4B H 0.6035 0.8492 0.4359 0.054 Uiso 1 1 calc R . .
C5 C 0.6783(12) 0.7304(15) 0.5153(9) 0.045(4) Uani 1 1 d DU . .
H5A H 0.6559 0.6644 0.5513 0.054 Uiso 1 1 calc R . .
H5B H 0.7044 0.8043 0.5452 0.054 Uiso 1 1 calc R . .
C6 C 0.6072(11) 0.4413(15) 0.2535(9) 0.040(4) Uani 1 1 d DU . .
C7 C 0.5600(12) 0.3078(15) 0.2675(9) 0.057(5) Uani 1 1 d DU . .
H7A H 0.5939 0.2453 0.2354 0.069 Uiso 1 1 calc R . .
H7B H 0.4850 0.3094 0.2548 0.069 Uiso 1 1 calc R . .
H7C H 0.5715 0.2846 0.3211 0.069 Uiso 1 1 calc R . .
C8 C 0.5649(11) 0.4959(14) 0.1774(8) 0.049(5) Uani 1 1 d DU . .
H8A H 0.5872 0.5844 0.1728 0.059 Uiso 1 1 calc R . .
H8B H 0.4885 0.4918 0.1755 0.059 Uiso 1 1 calc R . .
H8C H 0.5920 0.4461 0.1354 0.059 Uiso 1 1 calc R . .
C9 C 0.7266(10) 0.4357(15) 0.2575(9) 0.046(5) Uani 1 1 d DU . .
H9A H 0.7502 0.3633 0.2277 0.055 Uiso 1 1 calc R . .
H9B H 0.7512 0.4258 0.3106 0.055 Uiso 1 1 calc R . .
H9C H 0.7549 0.5144 0.2368 0.055 Uiso 1 1 calc R . .
C10 C 0.9043(12) 0.8314(16) 0.3692(10) 0.050(4) Uani 1 1 d DU . .
N4 N 0.9470(9) 0.9454(12) 0.3476(7) 0.043(3) Uani 1 1 d DU . .
C11 C 1.0546(11) 0.9518(16) 0.3773(9) 0.049(4) Uani 1 1 d DU . .
H11 H 1.1027 1.0189 0.3702 0.059 Uiso 1 1 calc R . .
C12 C 1.0726(12) 0.8424(16) 0.4173(9) 0.049(4) Uani 1 1 d DU . .
H12 H 1.1358 0.8206 0.4441 0.059 Uiso 1 1 calc R . .
N5 N 0.9824(10) 0.7676(12) 0.4122(7) 0.045(3) Uani 1 1 d DU . .
C13 C 0.9604(11) 0.6548(14) 0.4585(8) 0.040(4) Uani 1 1 d DU . .
H13A H 1.0235 0.6314 0.4895 0.048 Uiso 1 1 calc R . .
H13B H 0.9419 0.5824 0.4247 0.048 Uiso 1 1 calc R . .
C14 C 0.8703(11) 0.6819(15) 0.5108(8) 0.042(4) Uani 1 1 d DU . .
H14A H 0.8706 0.6181 0.5521 0.050 Uiso 1 1 calc R . .
H14B H 0.8799 0.7668 0.5342 0.050 Uiso 1 1 calc R . .
C15 C 0.8987(11) 1.0568(15) 0.2994(9) 0.046(4) Uani 1 1 d DU . .
C16 C 0.7801(10) 1.0596(17) 0.3147(10) 0.068(6) Uani 1 1 d DU . .
H16A H 0.7460 1.1248 0.2827 0.082 Uiso 1 1 calc R . .
H16B H 0.7703 1.0795 0.3684 0.082 Uiso 1 1 calc R . .
H16C H 0.7494 0.9765 0.3026 0.082 Uiso 1 1 calc R . .
C17 C 0.9218(12) 1.0289(14) 0.2158(9) 0.059(5) Uani 1 1 d DU . .
H17A H 0.8951 1.0984 0.1836 0.070 Uiso 1 1 calc R . .
H17B H 0.8878 0.9492 0.2001 0.070 Uiso 1 1 calc R . .
H17C H 0.9974 1.0211 0.2106 0.070 Uiso 1 1 calc R . .
C18 C 0.9506(12) 1.1829(14) 0.3257(10) 0.057(5) Uani 1 1 d DU . .
H18A H 1.0210 1.1880 0.3061 0.068 Uiso 1 1 calc R . .
H18B H 0.9548 1.1860 0.3814 0.068 Uiso 1 1 calc R . .
H18C H 0.9089 1.2547 0.3062 0.068 Uiso 1 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
Cl1 0.035(3) 0.065(4) 0.036(4) 0.006(2) -0.001(2) -0.003(2)
Cl2 0.028(3) 0.070(4) 0.055(3) 0.012(3) 0.007(2) 0.006(2)
Pd1 0.0246(10) 0.0547(13) 0.0330(12) 0.0009(7) 0.0001(7) -0.0019(7)
N3 0.026(7) 0.052(8) 0.052(9) 0.000(7) -0.013(7) 0.002(7)
C1 0.030(5) 0.044(6) 0.041(6) -0.002(4) -0.001(4) -0.003(4)
N1 0.023(6) 0.041(7) 0.040(8) 0.005(6) 0.001(6) -0.005(6)
C2 0.025(8) 0.048(10) 0.052(10) 0.005(8) -0.006(8) -0.015(8)
C3 0.028(8) 0.054(10) 0.055(10) 0.003(8) -0.003(9) -0.009(8)
N2 0.027(7) 0.047(8) 0.040(7) -0.006(6) 0.003(6) -0.006(6)
C4 0.038(9) 0.052(10) 0.044(10) -0.010(8) 0.002(8) -0.001(8)
C5 0.033(9) 0.055(9) 0.046(10) -0.003(8) -0.009(8) -0.002(8)
C6 0.032(9) 0.047(10) 0.040(10) 0.005(8) -0.004(8) -0.011(8)
C7 0.038(11) 0.075(14) 0.058(13) 0.001(11) -0.017(10) 0.008(10)
C8 0.044(11) 0.053(12) 0.049(13) -0.009(10) -0.009(9) -0.004(9)
C9 0.035(11) 0.060(12) 0.042(11) -0.002(10) 0.006(9) 0.025(10)
C10 0.034(9) 0.062(10) 0.053(10) -0.002(9) -0.001(8) -0.012(8)
N4 0.026(7) 0.057(9) 0.047(8) 0.002(7) 0.002(6) -0.005(7)
C11 0.026(8) 0.065(10) 0.056(10) 0.003(8) 0.004(8) -0.004(9)
C12 0.037(9) 0.061(11) 0.050(9) 0.009(8) 0.004(8) -0.013(9)
N5 0.042(8) 0.054(9) 0.039(8) 0.011(7) -0.003(7) -0.003(7)
C13 0.037(8) 0.049(10) 0.033(9) 0.009(8) -0.006(7) 0.004(8)
C14 0.039(9) 0.052(9) 0.034(9) 0.000(8) -0.008(8) -0.008(8)
C15 0.027(9) 0.059(10) 0.052(10) 0.009(9) 0.011(8) -0.007(8)
C16 0.041(12) 0.077(14) 0.087(14) 0.004(12) 0.007(11) 0.006(10)
C17 0.056(12) 0.052(12) 0.069(14) 0.023(11) 0.012(11) 0.001(10)
C18 0.034(11) 0.042(12) 0.095(15) 0.008(11) -0.008(10) -0.012(9)

_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
Cl1 Pd1 2.341(4) . ?
Pd1 C1 2.057(15) . ?
Pd1 N3 2.058(12) . ?
Pd1 C10 2.087(15) . ?
N3 C14 1.479(16) . ?
N3 C5 1.518(19) . ?
C1 N1 1.346(15) . ?
C1 N2 1.377(15) . ?
N1 C2 1.419(15) . ?
N1 C6 1.533(16) . ?
C2 C3 1.338(16) . ?
C3 N2 1.375(15) . ?
N2 C4 1.432(14) . ?
C4 C5 1.504(16) . ?
C6 C9 1.501(15) . ?
C6 C8 1.505(15) . ?
C6 C7 1.521(16) . ?
C10 N4 1.351(15) . ?
C10 N5 1.375(15) . ?
N4 C11 1.429(15) . ?
N4 C15 1.530(16) . ?
C11 C12 1.337(16) . ?
C12 N5 1.371(15) . ?
N5 C13 1.443(15) . ?
C13 C14 1.499(16) . ?
C15 C17 1.508(16) . ?
C15 C18 1.516(15) . ?
C15 C16 1.522(16) . ?

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 N3 82.1(5) . . ?
C1 Pd1 C10 171.4(7) . . ?
N3 Pd1 C10 89.7(6) . . ?
C1 Pd1 Cl1 92.8(4) . . ?
N3 Pd1 Cl1 173.4(4) . . ?
C10 Pd1 Cl1 95.6(5) . . ?
C14 N3 C5 110.8(11) . . ?
C14 N3 Pd1 118.7(9) . . ?
C5 N3 Pd1 116.0(9) . . ?
N1 C1 N2 105.1(12) . . ?
N1 C1 Pd1 141.7(11) . . ?
N2 C1 Pd1 113.1(10) . . ?
C1 N1 C2 110.2(12) . . ?
C1 N1 C6 127.9(12) . . ?
C2 N1 C6 121.9(11) . . ?
C3 C2 N1 106.4(13) . . ?
C2 C3 N2 107.9(14) . . ?
C3 N2 C1 110.5(12) . . ?
C3 N2 C4 127.2(13) . . ?
C1 N2 C4 122.2(12) . . ?
N2 C4 C5 112.6(12) . . ?
C4 C5 N3 110.3(13) . . ?
C9 C6 C8 111.9(12) . . ?
C9 C6 C7 110.6(13) . . ?
C8 C6 C7 110.5(12) . . ?
C9 C6 N1 109.7(11) . . ?
C8 C6 N1 106.9(12) . . ?
C7 C6 N1 107.0(12) . . ?
N4 C10 N5 106.4(13) . . ?
N4 C10 Pd1 138.1(12) . . ?
N5 C10 Pd1 115.5(11) . . ?
C10 N4 C11 108.8(12) . . ?
C10 N4 C15 130.5(12) . . ?
C11 N4 C15 120.7(11) . . ?
C12 C11 N4 106.6(13) . . ?
C11 C12 N5 108.6(14) . . ?
C12 N5 C10 109.7(13) . . ?
C12 N5 C13 126.4(13) . . ?
C10 N5 C13 122.4(13) . . ?
N5 C13 C14 110.3(12) . . ?
N3 C14 C13 110.8(12) . . ?
C17 C15 C18 110.6(12) . . ?
C17 C15 C16 113.2(13) . . ?
C18 C15 C16 110.2(13) . . ?
C17 C15 N4 106.7(12) . . ?
C18 C15 N4 109.0(12) . . ?
C16 C15 N4 106.9(11) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        40.87
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.111
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.116