# Electronic Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2011


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_d:\wrh\zcs\zcs-pd~1\w
_database_code_depnum_ccdc_archive 'CCDC 806910'
#TrackingRef 'ZCS-deposit.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H27 Cl3 N4 O2 Pd'
_chemical_formula_weight         508.16

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

_cell_length_a                   9.163(3)
_cell_length_b                   15.148(5)
_cell_length_c                   29.339(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4072(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      15

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2064
_exptl_absorpt_coefficient_mu    1.321
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7076
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29586
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4594
_reflns_number_gt                3835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0761P)^2^+0.1442P] 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         4594
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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 0.04543(2) 0.973315(14) 0.201439(7) 0.03679(11) Uani 1 1 d . . .
Cl1 Cl 0.10056(10) 0.93656(6) 0.12737(3) 0.0572(2) Uani 1 1 d . . .
Cl2 Cl -0.11028(10) 1.08266(5) 0.17808(3) 0.0585(2) Uani 1 1 d . . .
Cl3 Cl -0.18757(9) 1.12054(6) 0.45633(3) 0.0562(2) Uani 1 1 d . . .
O1 O -0.0067(4) 0.7343(2) 0.11800(11) 0.0828(8) Uani 1 1 d . . .
O2 O -0.3911(4) 1.2055(2) 0.38152(11) 0.0885(9) Uani 1 1 d . . .
N1 N 0.1720(2) 0.87797(14) 0.23124(7) 0.0357(5) Uani 1 1 d . . .
N2 N 0.0068(3) 0.99888(17) 0.26660(8) 0.0397(5) Uani 1 1 d . . .
N3 N 0.0203(3) 0.96086(16) 0.33863(8) 0.0402(5) Uani 1 1 d . . .
N4 N 0.3043(2) 1.13400(14) 0.48238(7) 0.0352(5) Uani 1 1 d . . .
C1 C 0.2566(3) 0.81946(19) 0.20933(10) 0.0420(6) Uani 1 1 d . . .
H1 H 0.2600 0.8206 0.1770 0.050 Uiso 1 1 calc R . .
C2 C 0.3392(3) 0.7574(2) 0.23258(11) 0.0485(7) Uani 1 1 d . . .
H2 H 0.3981 0.7165 0.2163 0.058 Uiso 1 1 calc R . .
C3 C 0.3351(4) 0.75557(19) 0.27943(12) 0.0509(7) Uani 1 1 d . . .
H3 H 0.3909 0.7133 0.2958 0.061 Uiso 1 1 calc R . .
C4 C 0.2489(4) 0.8158(2) 0.30241(10) 0.0458(7) Uani 1 1 d . . .
H4 H 0.2465 0.8160 0.3348 0.055 Uiso 1 1 calc R . .
C5 C 0.1656(3) 0.87621(17) 0.27784(9) 0.0361(6) Uani 1 1 d . . .
C6 C 0.0680(3) 0.9427(2) 0.29548(9) 0.0372(6) Uani 1 1 d . . .
C7 C -0.0804(4) 1.0552(2) 0.29067(12) 0.0468(7) Uani 1 1 d . . .
H7 H -0.1369 1.1021 0.2784 0.056 Uiso 1 1 calc R . .
C8 C -0.0718(4) 1.0322(2) 0.33510(13) 0.0506(8) Uani 1 1 d . . .
H8 H -0.1210 1.0603 0.3596 0.061 Uiso 1 1 calc R . .
C9 C 0.0457(4) 0.9118(2) 0.38089(11) 0.0513(8) Uani 1 1 d . . .
H9A H 0.0516 0.8480 0.3737 0.062 Uiso 1 1 calc R . .
H9B H -0.0388 0.9206 0.4014 0.062 Uiso 1 1 calc R . .
C10 C 0.1848(4) 0.93933(19) 0.40591(10) 0.0468(7) Uani 1 1 d . . .
H10A H 0.2039 0.8969 0.4309 0.056 Uiso 1 1 calc R . .
H10B H 0.2681 0.9364 0.3845 0.056 Uiso 1 1 calc R . .
C11 C 0.1760(3) 1.03164(18) 0.42568(10) 0.0422(6) Uani 1 1 d . . .
H11A H 0.1725 1.0755 0.4007 0.051 Uiso 1 1 calc R . .
H11B H 0.0859 1.0377 0.4440 0.051 Uiso 1 1 calc R . .
C12 C 0.3074(3) 1.04857(18) 0.45523(9) 0.0387(6) Uani 1 1 d . . .
H12A H 0.3952 1.0490 0.4356 0.046 Uiso 1 1 calc R . .
H12B H 0.3177 0.9988 0.4768 0.046 Uiso 1 1 calc R . .
C13 C 0.4423(3) 1.1406(2) 0.50922(12) 0.0526(8) Uani 1 1 d . . .
H13A H 0.5261 1.1376 0.4885 0.079 Uiso 1 1 calc R . .
H13B H 0.4473 1.0917 0.5310 0.079 Uiso 1 1 calc R . .
H13C H 0.4442 1.1968 0.5257 0.079 Uiso 1 1 calc R . .
C14 C 0.1793(3) 1.1341(2) 0.51493(11) 0.0506(7) Uani 1 1 d . . .
H14A H 0.1854 1.1863 0.5346 0.076 Uiso 1 1 calc R . .
H14B H 0.1831 1.0807 0.5338 0.076 Uiso 1 1 calc R . .
H14C H 0.0874 1.1353 0.4979 0.076 Uiso 1 1 calc R . .
C15 C 0.2938(5) 1.2117(2) 0.45133(11) 0.0610(9) Uani 1 1 d . . .
H15A H 0.2981 1.2662 0.4693 0.091 Uiso 1 1 calc R . .
H15B H 0.2012 1.2095 0.4346 0.091 Uiso 1 1 calc R . .
H15C H 0.3752 1.2106 0.4297 0.091 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
Pd1 0.03751(17) 0.03773(17) 0.03513(17) -0.00144(8) -0.00220(7) -0.00476(7)
Cl1 0.0667(5) 0.0692(5) 0.0357(4) -0.0034(4) -0.0015(4) -0.0011(4)
Cl2 0.0622(5) 0.0533(5) 0.0601(5) 0.0008(4) -0.0147(4) 0.0087(3)
Cl3 0.0520(4) 0.0589(5) 0.0578(5) -0.0041(4) 0.0059(3) 0.0044(3)
O1 0.0795(19) 0.0791(19) 0.090(2) -0.0057(17) 0.0127(18) -0.0168(16)
O2 0.109(3) 0.0682(18) 0.089(2) 0.0053(16) -0.0097(19) 0.0010(18)
N1 0.0349(11) 0.0375(11) 0.0348(12) -0.0016(9) 0.0011(9) -0.0045(8)
N2 0.0399(12) 0.0383(12) 0.0409(13) -0.0050(10) 0.0030(10) -0.0028(11)
N3 0.0452(14) 0.0433(13) 0.0322(13) -0.0058(10) 0.0076(10) -0.0073(10)
N4 0.0371(11) 0.0370(11) 0.0313(11) 0.0010(9) 0.0030(9) 0.0034(9)
C1 0.0409(15) 0.0441(15) 0.0411(14) -0.0085(12) 0.0017(12) -0.0023(12)
C2 0.0474(16) 0.0419(15) 0.0562(18) -0.0129(13) 0.0032(14) 0.0023(12)
C3 0.0534(18) 0.0386(15) 0.0606(19) -0.0009(14) -0.0063(15) 0.0036(13)
C4 0.0562(19) 0.0399(15) 0.0413(15) -0.0006(11) 0.0000(12) -0.0009(13)
C5 0.0387(14) 0.0350(13) 0.0347(13) -0.0029(10) 0.0020(10) -0.0074(10)
C6 0.0387(15) 0.0371(15) 0.0357(15) -0.0043(11) 0.0030(10) -0.0077(11)
C7 0.0417(16) 0.0428(16) 0.0560(19) -0.0097(14) 0.0039(14) 0.0014(13)
C8 0.0468(17) 0.0497(18) 0.055(2) -0.0181(14) 0.0125(15) -0.0036(13)
C9 0.070(2) 0.0472(17) 0.0364(16) -0.0005(13) 0.0143(14) -0.0167(14)
C10 0.067(2) 0.0363(14) 0.0376(14) -0.0016(12) 0.0038(13) -0.0006(13)
C11 0.0457(16) 0.0409(15) 0.0402(15) -0.0075(11) 0.0029(12) 0.0045(11)
C12 0.0445(15) 0.0355(13) 0.0362(14) -0.0015(11) 0.0043(11) 0.0080(11)
C13 0.0422(16) 0.065(2) 0.0505(19) -0.0071(16) -0.0072(13) 0.0015(13)
C14 0.0456(16) 0.0596(18) 0.0465(17) -0.0147(14) 0.0146(13) 0.0026(13)
C15 0.097(3) 0.0361(15) 0.0496(18) 0.0084(13) -0.0041(18) -0.0011(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 N2 1.982(2) . ?
Pd1 N1 2.048(2) . ?
Pd1 Cl2 2.2911(10) . ?
Pd1 Cl1 2.2994(10) . ?
N1 C1 1.342(4) . ?
N1 C5 1.369(4) . ?
N2 C6 1.326(4) . ?
N2 C7 1.366(4) . ?
N3 C6 1.367(4) . ?
N3 C8 1.375(4) . ?
N3 C9 1.464(4) . ?
N4 C14 1.491(3) . ?
N4 C15 1.492(4) . ?
N4 C13 1.493(4) . ?
N4 C12 1.520(3) . ?
C1 C2 1.386(4) . ?
C2 C3 1.375(5) . ?
C3 C4 1.382(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.443(4) . ?
C7 C8 1.352(5) . ?
C9 C10 1.530(5) . ?
C10 C11 1.516(4) . ?
C11 C12 1.505(4) . ?

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
N2 Pd1 N1 80.05(10) . . ?
N2 Pd1 Cl2 92.06(8) . . ?
N1 Pd1 Cl2 171.92(6) . . ?
N2 Pd1 Cl1 176.27(8) . . ?
N1 Pd1 Cl1 96.22(7) . . ?
Cl2 Pd1 Cl1 91.67(4) . . ?
C1 N1 C5 119.4(2) . . ?
C1 N1 Pd1 126.05(19) . . ?
C5 N1 Pd1 114.59(17) . . ?
C6 N2 C7 108.6(3) . . ?
C6 N2 Pd1 114.5(2) . . ?
C7 N2 Pd1 136.5(2) . . ?
C6 N3 C8 106.5(3) . . ?
C6 N3 C9 129.1(3) . . ?
C8 N3 C9 124.1(3) . . ?
C14 N4 C15 109.9(3) . . ?
C14 N4 C13 108.2(2) . . ?
C15 N4 C13 108.9(3) . . ?
C14 N4 C12 110.5(2) . . ?
C15 N4 C12 110.7(2) . . ?
C13 N4 C12 108.5(2) . . ?
N1 C1 C2 121.9(3) . . ?
C3 C2 C1 119.3(3) . . ?
C2 C3 C4 119.3(3) . . ?
C3 C4 C5 119.6(3) . . ?
N1 C5 C4 120.4(2) . . ?
N1 C5 C6 111.8(2) . . ?
C4 C5 C6 127.8(3) . . ?
N2 C6 N3 109.1(3) . . ?
N2 C6 C5 118.8(2) . . ?
N3 C6 C5 132.1(3) . . ?
C8 C7 N2 107.6(3) . . ?
C7 C8 N3 108.1(3) . . ?
N3 C9 C10 113.6(2) . . ?
C11 C10 C9 113.0(3) . . ?
C12 C11 C10 109.6(2) . . ?
C11 C12 N4 115.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.942
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.175