# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 182/1470
 
data_HG9901 
  
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C22 H24.50 N3 O4.25 Cl Pd'
_chemical_formula_weight          540.80 
_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' 
 'O'  'O'   0.0106   0.0060 
 '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            Monoclinic 
_symmetry_space_group_name_H-M    P2(1) 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
  
_cell_length_a                    12.399(2) 
_cell_length_b                    7.6006(7) 
_cell_length_c                    13.0976(11) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  108.603(8) 
_cell_angle_gamma                 90.00 
_cell_volume                      1169.8(2) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     28 
_cell_measurement_theta_min       4.66 
_cell_measurement_theta_max       12.50 
  
_exptl_crystal_description        prisms 
_exptl_crystal_colour             'Pale yellow' 
_exptl_crystal_size_max           0.61 
_exptl_crystal_size_mid           0.39 
_exptl_crystal_size_min           0.21 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.535 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              549 
_exptl_absorpt_coefficient_mu     0.941 
_exptl_absorpt_correction_type    'Face-indexed numerical' 
_exptl_absorpt_correction_T_min   0.7529 
_exptl_absorpt_correction_T_max   0.8635 
  
_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        'Siemens P4' 
_diffrn_measurement_method        '\w scans' 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  97 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             3005 
_diffrn_reflns_av_R_equivalents   0.0220 
_diffrn_reflns_av_sigmaI/netI     0.0438 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          1.97 
_diffrn_reflns_theta_max          27.50 
_reflns_number_total              2879 
_reflns_number_observed           2628 
_reflns_observed_criterion        >2sigma(I) 
  
_computing_data_collection        'Siemens XSCANS' 
_computing_cell_refinement        'Siemens XSCANS' 
_computing_data_reduction         'Siemens SHELXTL' 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'Siemens SHELXTL' 
_computing_publication_material   'Siemens SHELXTL' 
  
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections except for 47 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^)+(0.0396P)^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     ? 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.01(5) 
_refine_ls_number_reflns          2832 
_refine_ls_number_parameters      284 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0369 
_refine_ls_R_factor_obs           0.0321 
_refine_ls_wR_factor_all          0.0795 
_refine_ls_wR_factor_obs          0.0768 
_refine_ls_goodness_of_fit_all    1.031 
_refine_ls_goodness_of_fit_obs    1.051 
_refine_ls_restrained_S_all       1.035 
_refine_ls_restrained_S_obs       1.051 
_refine_ls_shift/esd_max          0.001 
_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 
Pd Pd 0.14824(3) 0.50092(8) 0.75478(2) 0.03937(9) Uani 1 d . . 
C1 C 0.1881(4) 0.5600(7) 0.6224(3) 0.0344(8) Uani 1 d . . 
C2 C 0.1129(4) 0.5576(6) 0.5121(3) 0.0344(8) Uani 1 d . . 
C3 C 0.0040(4) 0.4805(11) 0.4824(4) 0.0436(14) Uani 1 d . . 
H3A H -0.0194(4) 0.4231(11) 0.5344(4) 0.052 Uiso 1 calc R . 
C4 C -0.0689(4) 0.4880(15) 0.3779(4) 0.0502(13) Uani 1 d . . 
H4A H -0.1411(4) 0.4385(15) 0.3605(4) 0.060 Uiso 1 calc R . 
C5 C -0.0339(5) 0.5704(9) 0.2982(4) 0.0521(12) Uani 1 d . . 
H5A H -0.0838(5) 0.5792(9) 0.2282(4) 0.062 Uiso 1 calc R . 
C6 C 0.0737(5) 0.6379(8) 0.3232(4) 0.0455(11) Uani 1 d . . 
H6A H 0.0968(5) 0.6894(8) 0.2692(4) 0.055 Uiso 1 calc R . 
C7 C 0.1509(4) 0.6311(7) 0.4298(3) 0.0370(9) Uani 1 d . . 
C8 C 0.2678(4) 0.6958(7) 0.4560(4) 0.0416(10) Uani 1 d . . 
C9 C 0.3114(5) 0.7637(9) 0.3763(5) 0.0537(13) Uani 1 d . . 
H9A H 0.2656(5) 0.7649(9) 0.3045(5) 0.064 Uiso 1 calc R . 
C10 C 0.4215(6) 0.8285(11) 0.4041(6) 0.066(2) Uani 1 d . . 
H10A H 0.4491(6) 0.8724(11) 0.3509(6) 0.079 Uiso 1 calc R . 
C11 C 0.4906(5) 0.8283(11) 0.5102(7) 0.064(2) Uani 1 d . . 
H11A H 0.5629(5) 0.8775(11) 0.5286(7) 0.077 Uiso 1 calc R . 
C12 C 0.4525(4) 0.7554(8) 0.5889(5) 0.0514(13) Uani 1 d . . 
H12A H 0.5011(4) 0.7508(8) 0.6596(5) 0.062 Uiso 1 calc R . 
C13 C 0.3406(4) 0.6873(7) 0.5638(4) 0.0386(9) Uani 1 d . . 
C14 C 0.2979(4) 0.6149(6) 0.6452(4) 0.0353(8) Uani 1 d . . 
C15 C 0.3715(4) 0.6038(8) 0.7628(4) 0.0428(11) Uani 1 d . . 
H15A H 0.4493(4) 0.5724(8) 0.7665(4) 0.051 Uiso 1 calc R . 
N16 N 0.3212(4) 0.4553(7) 0.8107(3) 0.0468(12) Uani 1 d . . 
C17 C 0.3735(6) 0.7795(10) 0.8193(5) 0.062(2) Uani 1 d . . 
H17A H 0.4203(6) 0.7697(10) 0.8933(5) 0.094 Uiso 1 calc R . 
H17B H 0.2975(6) 0.8110(10) 0.8160(5) 0.094 Uiso 1 calc R . 
H17C H 0.4040(6) 0.8685(10) 0.7843(5) 0.094 Uiso 1 calc R . 
C18 C 0.3701(5) 0.4550(13) 0.9307(4) 0.072(3) Uani 1 d . . 
H18A H 0.3539(5) 0.5652(13) 0.9584(4) 0.108 Uiso 1 calc R . 
H18B H 0.4510(5) 0.4384(13) 0.9513(4) 0.108 Uiso 1 calc R . 
H18C H 0.3369(5) 0.3610(13) 0.9594(4) 0.108 Uiso 1 calc R . 
C19 C 0.3487(6) 0.2822(9) 0.7724(7) 0.060(2) Uani 1 d . . 
H19A H 0.3185(6) 0.2775(9) 0.6952(7) 0.090 Uiso 1 calc R . 
H19B H 0.3157(6) 0.1899(9) 0.8027(7) 0.090 Uiso 1 calc R . 
H19C H 0.4298(6) 0.2673(9) 0.7945(7) 0.090 Uiso 1 calc R . 
N20 N 0.1172(5) 0.4428(9) 0.9017(4) 0.0603(15) Uani 1 d . . 
C21 C 0.0983(6) 0.4177(12) 0.9786(5) 0.067(2) Uani 1 d . . 
C22 C 0.0758(9) 0.3898(18) 1.0799(6) 0.104(4) Uani 1 d . . 
H22A H 0.0856(9) 0.2675(18) 1.0990(6) 0.156 Uiso 1 d R . 
H22B H -0.0009(9) 0.4245(18) 1.0720(6) 0.156 Uiso 1 d R . 
H22C H 0.1277(9) 0.4589(18) 1.1355(6) 0.156 Uiso 1 d R . 
N23 N -0.0157(4) 0.5811(7) 0.6978(4) 0.0459(10) Uani 1 d . . 
C24 C -0.1067(5) 0.6321(9) 0.6693(5) 0.0506(12) Uani 1 d . . 
C25 C -0.2219(5) 0.6985(11) 0.6277(7) 0.075(2) Uani 1 d . . 
H25A H -0.2444(5) 0.7458(11) 0.6857(7) 0.112 Uiso 1 d R . 
H25B H -0.2723(5) 0.6044(11) 0.5939(7) 0.112 Uiso 1 d R . 
H25C H -0.2254(5) 0.7892(11) 0.5757(7) 0.112 Uiso 1 d R . 
Cl Cl 0.73536(14) 0.4631(3) 0.91890(13) 0.0705(7) Uani 1 d . . 
O1 O 0.7772(6) 0.5127(24) 1.0267(5) 0.132(3) Uani 1 d . . 
O2 O 0.8243(7) 0.4302(20) 0.8806(6) 0.161(7) Uani 1 d . . 
O3 O 0.6601(11) 0.3302(19) 0.8986(9) 0.154(5) Uani 1 d . . 
O4 O 0.6741(12) 0.6064(22) 0.8566(10) 0.183(6) Uani 1 d . . 
O10 O 0.3337(33) 0.4655(77) 1.1993(31) 0.150(15) Uiso 0.25 d P . 
  
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 
Pd 0.03668(13) 0.0478(2) 0.03491(13) 0.0057(2) 0.01321(9) 0.0045(3) 
C1 0.036(2) 0.034(2) 0.034(2) 0.0013(15) 0.013(2) 0.002(2) 
C2 0.038(2) 0.031(2) 0.034(2) 0.0002(14) 0.012(2) 0.001(2) 
C3 0.045(2) 0.043(4) 0.043(2) -0.005(2) 0.014(2) -0.009(2) 
C4 0.045(2) 0.050(4) 0.048(2) -0.003(3) 0.005(2) -0.010(3) 
C5 0.055(3) 0.057(3) 0.037(2) -0.003(2) 0.003(2) -0.004(2) 
C6 0.055(3) 0.045(3) 0.036(2) -0.001(2) 0.013(2) 0.005(2) 
C7 0.041(2) 0.035(2) 0.035(2) -0.004(2) 0.013(2) 0.004(2) 
C8 0.047(2) 0.038(2) 0.045(2) 0.004(2) 0.022(2) 0.005(2) 
C9 0.058(3) 0.057(3) 0.055(3) 0.015(3) 0.030(3) 0.009(3) 
C10 0.062(4) 0.068(4) 0.085(4) 0.023(4) 0.047(3) 0.002(3) 
C11 0.041(3) 0.069(4) 0.090(4) 0.022(4) 0.030(3) -0.002(3) 
C12 0.037(2) 0.051(3) 0.067(3) 0.010(3) 0.016(2) -0.002(2) 
C13 0.034(2) 0.034(2) 0.050(2) 0.003(2) 0.017(2) 0.003(2) 
C14 0.037(2) 0.032(2) 0.037(2) 0.003(2) 0.012(2) 0.005(2) 
C15 0.029(2) 0.050(3) 0.044(2) 0.005(2) 0.004(2) 0.005(2) 
N16 0.039(2) 0.058(4) 0.040(2) 0.009(2) 0.007(2) 0.006(2) 
C17 0.067(4) 0.055(4) 0.055(3) -0.010(3) 0.004(3) -0.003(3) 
C18 0.052(3) 0.117(9) 0.041(2) 0.019(3) 0.006(2) 0.010(4) 
C19 0.054(3) 0.043(3) 0.087(5) 0.017(3) 0.028(3) 0.015(3) 
N20 0.060(3) 0.081(4) 0.044(2) 0.011(2) 0.022(2) 0.012(3) 
C21 0.069(4) 0.094(5) 0.044(3) 0.007(3) 0.025(3) 0.015(4) 
C22 0.120(7) 0.156(11) 0.053(4) 0.028(5) 0.051(4) 0.045(7) 
N23 0.038(2) 0.055(3) 0.049(2) 0.005(2) 0.020(2) 0.002(2) 
C24 0.043(3) 0.055(3) 0.057(3) 0.007(3) 0.019(2) -0.001(2) 
C25 0.037(3) 0.060(4) 0.120(6) 0.020(4) 0.016(3) -0.001(3) 
Cl 0.0563(7) 0.102(2) 0.0530(6) -0.0087(8) 0.0174(5) -0.0146(9) 
O1 0.133(5) 0.192(9) 0.065(3) -0.032(8) 0.024(3) -0.021(11) 
O2 0.088(4) 0.297(21) 0.111(5) -0.057(8) 0.051(4) 0.000(7) 
O3 0.138(8) 0.178(12) 0.140(9) -0.008(8) 0.038(7) -0.078(9) 
O4 0.159(11) 0.196(14) 0.153(10) 0.066(10) -0.007(8) 0.002(10) 
  
_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 
Pd C1 2.000(4) . ? 
Pd N23 2.023(4) . ? 
Pd N16 2.062(4) . ? 
Pd N20 2.126(5) . ? 
C1 C14 1.363(6) . ? 
C1 C2 1.448(6) . ? 
C2 C3 1.409(7) . ? 
C2 C7 1.421(6) . ? 
C3 C4 1.379(6) . ? 
C4 C5 1.400(9) . ? 
C5 C6 1.368(8) . ? 
C6 C7 1.420(6) . ? 
C7 C8 1.464(7) . ? 
C8 C13 1.413(7) . ? 
C8 C9 1.418(7) . ? 
C9 C10 1.387(9) . ? 
C10 C11 1.380(11) . ? 
C11 C12 1.380(8) . ? 
C12 C13 1.418(7) . ? 
C13 C14 1.442(6) . ? 
C14 C15 1.521(6) . ? 
C15 N16 1.519(7) . ? 
C15 C17 1.523(9) . ? 
N16 C19 1.486(8) . ? 
N16 C18 1.493(6) . ? 
N20 C21 1.121(8) . ? 
C21 C22 1.456(8) . ? 
N23 C24 1.137(7) . ? 
C24 C25 1.448(8) . ? 
Cl O3 1.343(11) . ? 
Cl O2 1.372(7) . ? 
Cl O1 1.392(7) . ? 
Cl O4 1.426(14) . ? 
  
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 Pd N23 96.3(2) . . ? 
C1 Pd N16 80.2(2) . . ? 
N23 Pd N16 172.0(2) . . ? 
C1 Pd N20 176.2(2) . . ? 
N23 Pd N20 86.9(2) . . ? 
N16 Pd N20 96.4(2) . . ? 
C14 C1 C2 120.2(4) . . ? 
C14 C1 Pd 112.6(3) . . ? 
C2 C1 Pd 127.1(3) . . ? 
C3 C2 C7 118.4(4) . . ? 
C3 C2 C1 122.4(4) . . ? 
C7 C2 C1 119.2(4) . . ? 
C4 C3 C2 121.6(6) . . ? 
C3 C4 C5 119.8(6) . . ? 
C6 C5 C4 120.0(5) . . ? 
C5 C6 C7 121.4(5) . . ? 
C6 C7 C2 118.5(5) . . ? 
C6 C7 C8 121.7(5) . . ? 
C2 C7 C8 119.8(4) . . ? 
C13 C8 C9 118.7(5) . . ? 
C13 C8 C7 119.2(4) . . ? 
C9 C8 C7 122.1(5) . . ? 
C10 C9 C8 120.7(6) . . ? 
C11 C10 C9 120.4(5) . . ? 
C10 C11 C12 120.2(6) . . ? 
C11 C12 C13 121.0(6) . . ? 
C8 C13 C12 118.7(5) . . ? 
C8 C13 C14 119.2(4) . . ? 
C12 C13 C14 122.0(5) . . ? 
C1 C14 C13 122.1(4) . . ? 
C1 C14 C15 116.1(4) . . ? 
C13 C14 C15 121.8(4) . . ? 
N16 C15 C14 105.5(4) . . ? 
N16 C15 C17 113.3(5) . . ? 
C14 C15 C17 110.8(4) . . ? 
C19 N16 C18 107.1(5) . . ? 
C19 N16 C15 110.5(5) . . ? 
C18 N16 C15 110.7(5) . . ? 
C19 N16 Pd 110.7(4) . . ? 
C18 N16 Pd 113.7(3) . . ? 
C15 N16 Pd 104.3(3) . . ? 
C21 N20 Pd 177.4(7) . . ? 
N20 C21 C22 178.3(11) . . ? 
C24 N23 Pd 176.8(5) . . ? 
N23 C24 C25 177.1(7) . . ? 
O3 Cl O2 112.3(9) . . ? 
O3 Cl O1 114.5(8) . . ? 
O2 Cl O1 109.7(5) . . ? 
O3 Cl O4 104.6(7) . . ? 
O2 Cl O4 105.9(9) . . ? 
O1 Cl O4 109.4(10) . . ? 
  
_refine_diff_density_max    0.360 
_refine_diff_density_min   -0.266 
_refine_diff_density_rms    0.069