# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010



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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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data_1
_database_code_depnum_ccdc_archive 'CCDC 767347'
#TrackingRef 'data1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl2 N2 Pd'
_chemical_formula_weight         465.68

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           Hexagonal
_symmetry_space_group_name_H-M   P6(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   18.7436(5)
_cell_length_b                   18.7436(5)
_cell_length_c                   13.3951(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     4075.5(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9784
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      29.91

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1404
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8094
_exptl_absorpt_correction_T_max  0.9327
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'

_exptl_special_details           
;
'Blessing, Acta Cryst. (1995) A51, 33-38'
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 512x512
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26919
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.25
_diffrn_reflns_theta_max         29.97
_reflns_number_total             6978
_reflns_number_gt                6054
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0703P)^2^+1.8637P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_number_reflns         6978
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 0.577736(17) 0.750541(17) 0.66999(4) 0.04642(9) Uani 1 1 d . . .
Cl1 Cl 0.63190(8) 0.69152(8) 0.56924(11) 0.0652(3) Uani 1 1 d . . .
Cl2 Cl 0.51074(7) 0.63242(7) 0.76566(10) 0.0631(3) Uani 1 1 d . . .
N1 N 0.5331(2) 0.8119(2) 0.7516(3) 0.0517(8) Uani 1 1 d . . .
C2 C 0.5115(3) 0.7985(3) 0.8460(5) 0.0697(13) Uani 1 1 d . . .
H2 H 0.5161 0.7581 0.8807 0.084 Uiso 1 1 calc R . .
C3 C 0.4821(4) 0.8435(5) 0.8942(6) 0.091(2) Uani 1 1 d . . .
H3 H 0.4659 0.8334 0.9607 0.110 Uiso 1 1 calc R . .
C4 C 0.4776(4) 0.9037(4) 0.8410(8) 0.092(2) Uani 1 1 d . . .
H4 H 0.4570 0.9343 0.8713 0.110 Uiso 1 1 calc R . .
C5 C 0.5030(3) 0.9190(3) 0.7444(7) 0.0807(19) Uani 1 1 d . . .
H5 H 0.5020 0.9613 0.7093 0.097 Uiso 1 1 calc R . .
C6 C 0.5303(3) 0.8710(3) 0.6990(4) 0.0585(11) Uani 1 1 d . . .
C7 C 0.5601(3) 0.8828(3) 0.5930(4) 0.0537(10) Uani 1 1 d . . .
H7 H 0.5865 0.9416 0.5769 0.064 Uiso 1 1 calc R . .
C8 C 0.4898(3) 0.8363(3) 0.5216(4) 0.0589(11) Uani 1 1 d . . .
C9 C 0.4267(4) 0.7551(4) 0.5362(6) 0.0841(19) Uani 1 1 d . . .
H9 H 0.4268 0.7265 0.5929 0.101 Uiso 1 1 calc R . .
C10 C 0.3650(5) 0.7176(4) 0.4675(7) 0.107(3) Uani 1 1 d . . .
H10 H 0.3242 0.6631 0.4775 0.128 Uiso 1 1 calc R . .
C11 C 0.3617(5) 0.7576(5) 0.3854(7) 0.104(3) Uani 1 1 d . . .
H11 H 0.3197 0.7308 0.3389 0.125 Uiso 1 1 calc R . .
C12 C 0.4205(6) 0.8377(8) 0.3718(8) 0.136(4) Uani 1 1 d . . .
H12 H 0.4176 0.8656 0.3160 0.163 Uiso 1 1 calc R . .
C13 C 0.4837(4) 0.8782(5) 0.4377(7) 0.099(3) Uani 1 1 d . . .
H13 H 0.5227 0.9332 0.4272 0.118 Uiso 1 1 calc R . .
N14 N 0.6243(2) 0.8558(2) 0.5828(3) 0.0483(7) Uani 1 1 d . . .
H14 H 0.6233 0.8402 0.5183 0.058 Uiso 1 1 calc R . .
C15 C 0.7107(3) 0.9257(3) 0.6041(4) 0.0592(11) Uani 1 1 d . . .
H15 H 0.7175 0.9739 0.5674 0.071 Uiso 1 1 calc R . .
C16 C 0.7253(3) 0.9491(3) 0.7110(4) 0.0585(12) Uani 1 1 d . . .
C17 C 0.7193(4) 1.0160(4) 0.7461(6) 0.0795(16) Uani 1 1 d . . .
H17 H 0.7056 1.0452 0.7014 0.095 Uiso 1 1 calc R . .
C18 C 0.7333(5) 1.0409(5) 0.8464(7) 0.098(2) Uani 1 1 d . . .
H18 H 0.7253 1.0830 0.8703 0.118 Uiso 1 1 calc R . .
C19 C 0.7593(6) 1.0000(7) 0.9068(8) 0.124(3) Uani 1 1 d . . .
H19 H 0.7762 1.0201 0.9711 0.149 Uiso 1 1 calc R . .
C20 C 0.7620(5) 0.9339(6) 0.8802(7) 0.108(3) Uani 1 1 d . . .
H20 H 0.7726 0.9040 0.9274 0.130 Uiso 1 1 calc R . .
C21 C 0.7487(4) 0.9089(4) 0.7803(6) 0.0753(17) Uani 1 1 d . . .
H21 H 0.7556 0.8653 0.7598 0.090 Uiso 1 1 calc R . .
C22 C 0.7723(4) 0.9030(5) 0.5596(7) 0.095(2) Uani 1 1 d . . .
H22A H 0.8273 0.9438 0.5782 0.142 Uiso 1 1 calc R . .
H22B H 0.7675 0.9006 0.4882 0.142 Uiso 1 1 calc R . .
H22C H 0.7605 0.8502 0.5847 0.142 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 0.04600(15) 0.04558(15) 0.04784(16) 0.00408(13) -0.00112(12) 0.02300(12)
Cl1 0.0704(7) 0.0629(6) 0.0708(8) -0.0044(6) 0.0005(6) 0.0398(5)
Cl2 0.0639(6) 0.0579(6) 0.0621(7) 0.0139(5) 0.0016(5) 0.0265(5)
N1 0.0487(16) 0.0512(17) 0.056(2) 0.0018(16) -0.0004(16) 0.0253(14)
C2 0.069(3) 0.064(3) 0.066(3) -0.007(3) 0.012(3) 0.026(2)
C3 0.087(4) 0.088(4) 0.086(5) -0.014(4) 0.020(4) 0.035(4)
C4 0.071(3) 0.087(4) 0.116(6) -0.030(4) 0.008(4) 0.039(3)
C5 0.063(3) 0.063(3) 0.121(6) -0.014(3) -0.002(3) 0.035(2)
C6 0.0442(19) 0.051(2) 0.077(3) -0.004(2) -0.0070(19) 0.0218(17)
C7 0.052(2) 0.0447(18) 0.063(3) 0.0026(19) -0.009(2) 0.0231(17)
C8 0.055(2) 0.061(2) 0.063(3) 0.010(2) -0.005(2) 0.0309(19)
C9 0.076(3) 0.065(3) 0.096(5) 0.006(3) -0.031(3) 0.024(3)
C10 0.094(5) 0.074(4) 0.133(7) -0.003(4) -0.056(5) 0.028(3)
C11 0.089(4) 0.107(5) 0.104(6) 0.014(4) -0.032(4) 0.041(4)
C12 0.107(6) 0.159(9) 0.115(7) 0.053(6) -0.026(5) 0.046(6)
C13 0.072(3) 0.098(5) 0.102(6) 0.036(4) -0.027(4) 0.025(3)
N14 0.0521(17) 0.0518(17) 0.0438(18) 0.0056(14) -0.0027(15) 0.0281(14)
C15 0.046(2) 0.059(2) 0.066(3) 0.014(2) 0.002(2) 0.0223(18)
C16 0.0420(19) 0.0450(19) 0.080(3) 0.008(2) -0.011(2) 0.0151(16)
C17 0.075(3) 0.071(3) 0.092(5) -0.003(3) -0.005(3) 0.036(3)
C18 0.096(5) 0.093(5) 0.097(6) -0.014(4) -0.006(4) 0.040(4)
C19 0.129(7) 0.115(7) 0.095(7) -0.020(6) -0.016(6) 0.036(6)
C20 0.112(6) 0.096(5) 0.085(6) 0.014(4) -0.036(4) 0.029(5)
C21 0.076(3) 0.062(3) 0.077(4) 0.005(3) -0.017(3) 0.027(3)
C22 0.063(3) 0.097(4) 0.115(6) -0.014(4) 0.013(4) 0.033(3)

_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 N1 2.046(4) . ?
Pd1 N14 2.073(4) . ?
Pd1 Cl1 2.2801(13) . ?
Pd1 Cl2 2.3111(12) . ?
N1 C2 1.313(8) . ?
N1 C6 1.335(6) . ?
C2 C3 1.376(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(8) . ?
C7 C8 1.504(7) . ?
C7 N14 1.527(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.398(7) . ?
C8 C13 1.407(8) . ?
C9 C10 1.366(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.350(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(12) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N14 C15 1.516(6) . ?
N14 H14 0.9100 . ?
C15 C16 1.483(8) . ?
C15 C22 1.536(9) . ?
C15 H15 0.9800 . ?
C16 C17 1.396(8) . ?
C16 C21 1.397(8) . ?
C17 C18 1.403(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.361(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.314(13) . ?
C19 H19 0.9300 . ?
C20 C21 1.398(12) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
N1 Pd1 N14 82.04(15) . . ?
N1 Pd1 Cl1 174.94(12) . . ?
N14 Pd1 Cl1 92.91(11) . . ?
N1 Pd1 Cl2 93.63(12) . . ?
N14 Pd1 Cl2 173.14(10) . . ?
Cl1 Pd1 Cl2 91.37(5) . . ?
C2 N1 C6 122.1(5) . . ?
C2 N1 Pd1 125.5(4) . . ?
C6 N1 Pd1 112.4(3) . . ?
N1 C2 C3 120.9(6) . . ?
N1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 117.9(7) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C5 C4 C3 120.6(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.1(7) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 119.3(6) . . ?
N1 C6 C7 117.1(4) . . ?
C5 C6 C7 123.5(5) . . ?
C6 C7 C8 111.3(4) . . ?
C6 C7 N14 109.4(4) . . ?
C8 C7 N14 111.0(4) . . ?
C6 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
N14 C7 H7 108.4 . . ?
C9 C8 C13 117.3(5) . . ?
C9 C8 C7 124.1(5) . . ?
C13 C8 C7 118.5(5) . . ?
C10 C9 C8 120.2(6) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 121.7(7) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.0(7) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 121.8(8) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C8 119.8(7) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C15 N14 C7 112.1(3) . . ?
C15 N14 Pd1 118.4(3) . . ?
C7 N14 Pd1 103.8(3) . . ?
C15 N14 H14 107.3 . . ?
C7 N14 H14 107.3 . . ?
Pd1 N14 H14 107.3 . . ?
C16 C15 N14 113.3(4) . . ?
C16 C15 C22 113.8(5) . . ?
N14 C15 C22 108.3(5) . . ?
C16 C15 H15 107.0 . . ?
N14 C15 H15 107.0 . . ?
C22 C15 H15 107.0 . . ?
C17 C16 C21 116.7(6) . . ?
C17 C16 C15 120.3(5) . . ?
C21 C16 C15 122.9(5) . . ?
C18 C17 C16 122.4(7) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C19 C18 C17 116.2(8) . . ?
C19 C18 H18 121.9 . . ?
C17 C18 H18 121.9 . . ?
C20 C19 C18 124.2(9) . . ?
C20 C19 H19 117.9 . . ?
C18 C19 H19 117.9 . . ?
C19 C20 C21 119.5(8) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 120.4(7) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C15 C22 H22A 109.5 . . ?
C15 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C15 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        29.97
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.096
#===END