# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 N4 O6 Pd2'
_chemical_formula_weight         376.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   16.5855(3)
_cell_length_b                   15.6566(3)
_cell_length_c                   14.3263(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.686(8)
_cell_angle_gamma                90.00
_cell_volume                     3263.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    19165
_cell_measurement_theta_min      6.70
_cell_measurement_theta_max      68.20

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    9.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.115
_exptl_absorpt_correction_T_max  0.155
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(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  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20138
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.66
_diffrn_reflns_theta_max         68.21
_reflns_number_total             2957
_reflns_number_gt                2708
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_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^ > 2\s(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^)+(0.2000P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2957
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0896
_refine_ls_wR_factor_ref         0.3543
_refine_ls_wR_factor_gt          0.3222
_refine_ls_goodness_of_fit_ref   1.751
_refine_ls_restrained_S_all      1.751
_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
Pd1 Pd 0.95042(4) 0.02530(3) 0.81582(5) 0.0404(5) Uani 1 1 d . . .
O1 O 1.0615(5) -0.0507(5) 0.9054(6) 0.0582(17) Uani 1 1 d . . .
O2 O 0.8859(4) -0.0701(3) 0.7098(6) 0.0511(16) Uani 1 1 d . . .
O3 O 0.8070(7) 0.2448(5) 0.7544(8) 0.094(3) Uani 1 1 d . . .
N1 N 0.9987(5) 0.1218(5) 0.9196(5) 0.0459(17) Uani 1 1 d . . .
N2 N 0.8448(5) 0.1061(5) 0.7429(6) 0.0471(16) Uani 1 1 d . . .
C1 C 0.8839(6) -0.0817(6) 0.6207(9) 0.052(2) Uani 1 1 d . . .
C2 C 1.0772(7) 0.1205(7) 1.0111(8) 0.055(2) Uani 1 1 d . . .
H2 H 1.1125 0.0711 1.0327 0.067 Uiso 1 1 calc R . .
C3 C 1.1062(8) 0.1941(10) 1.0744(8) 0.074(4) Uani 1 1 d . . .
H3 H 1.1616 0.1935 1.1376 0.089 Uiso 1 1 calc R . .
C4 C 1.0553(9) 0.2650(8) 1.0451(8) 0.068(3) Uani 1 1 d . . .
H4 H 1.0746 0.3137 1.0875 0.081 Uiso 1 1 calc R . .
C5 C 0.9710(9) 0.2648(7) 0.9480(11) 0.071(3) Uani 1 1 d . . .
H5 H 0.9349 0.3137 0.9248 0.085 Uiso 1 1 calc R . .
C6 C 0.9433(7) 0.1890(6) 0.8878(8) 0.053(2) Uani 1 1 d . . .
C7 C 0.8563(6) 0.1837(6) 0.7859(8) 0.053(2) Uani 1 1 d . . .
C10 C 0.7651(6) 0.0905(6) 0.6419(7) 0.0480(19) Uani 1 1 d . . .
C11 C 0.6998(7) 0.0310(5) 0.6345(11) 0.053(3) Uani 1 1 d . . .
C12 C 0.6266(9) 0.0143(7) 0.5355(12) 0.065(3) Uani 1 1 d . . .
H12 H 0.5827 -0.0254 0.5297 0.078 Uiso 1 1 calc R . .
C13 C 0.6166(9) 0.0537(8) 0.4463(9) 0.071(3) Uani 1 1 d . . .
H13 H 0.5667 0.0408 0.3805 0.085 Uiso 1 1 calc R . .
C14 C 0.6828(8) 0.1150(7) 0.4537(8) 0.063(3) Uani 1 1 d . . .
H14 H 0.6770 0.1418 0.3928 0.075 Uiso 1 1 calc R . .
C15 C 0.7585(7) 0.1351(7) 0.5556(8) 0.056(2) Uani 1 1 d . . .
H15 H 0.8014 0.1766 0.5633 0.068 Uiso 1 1 calc R . .
C16 C 0.7088(9) -0.0144(9) 0.7347(11) 0.070(3) Uani 1 1 d . . .
H16A H 0.7374 0.0234 0.7947 0.104 Uiso 1 1 calc R . .
H16B H 0.7458 -0.0648 0.7482 0.104 Uiso 1 1 calc R . .
H16C H 0.6489 -0.0301 0.7237 0.104 Uiso 1 1 calc R . .
C17 C 0.8079(9) -0.1346(9) 0.5427(12) 0.092(5) Uani 1 1 d . . .
H17A H 0.8257 -0.1601 0.4944 0.137 Uiso 1 1 calc R . .
H17B H 0.7546 -0.0995 0.5036 0.137 Uiso 1 1 calc R . .
H17C H 0.7939 -0.1787 0.5793 0.137 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 0.0323(7) 0.0398(7) 0.0461(7) 0.00459(19) 0.0164(5) 0.00113(17)
O1 0.047(4) 0.066(4) 0.055(4) 0.018(4) 0.020(3) 0.009(4)
O2 0.040(3) 0.037(3) 0.070(4) -0.001(3) 0.021(3) -0.002(2)
O3 0.090(7) 0.060(5) 0.086(6) -0.020(4) 0.006(5) 0.028(5)
N1 0.045(4) 0.061(4) 0.031(3) 0.000(3) 0.018(3) -0.010(3)
N2 0.039(4) 0.040(4) 0.058(4) -0.003(3) 0.019(3) -0.004(3)
C1 0.035(4) 0.045(5) 0.069(6) -0.011(4) 0.018(4) 0.001(3)
C2 0.046(5) 0.064(6) 0.056(5) 0.003(4) 0.024(4) -0.008(4)
C3 0.052(6) 0.119(11) 0.045(5) -0.018(6) 0.018(4) -0.046(7)
C4 0.087(8) 0.053(6) 0.049(5) -0.017(5) 0.021(5) -0.030(6)
C5 0.074(8) 0.037(5) 0.089(8) -0.012(5) 0.028(6) -0.015(5)
C6 0.053(5) 0.048(5) 0.055(5) -0.004(4) 0.023(4) -0.004(4)
C7 0.051(5) 0.041(5) 0.057(5) -0.006(4) 0.018(4) 0.004(4)
C10 0.045(5) 0.048(4) 0.047(5) -0.005(4) 0.019(4) 0.002(4)
C11 0.035(5) 0.048(5) 0.076(7) 0.004(4) 0.027(5) 0.002(3)
C12 0.045(6) 0.058(6) 0.082(8) -0.010(5) 0.023(6) -0.006(4)
C13 0.061(7) 0.075(7) 0.052(6) -0.009(6) 0.007(5) 0.010(6)
C14 0.059(6) 0.065(6) 0.057(6) 0.002(5) 0.021(5) 0.018(5)
C15 0.058(6) 0.060(6) 0.052(5) 0.004(4) 0.027(5) 0.016(4)
C16 0.056(7) 0.084(9) 0.065(7) 0.010(5) 0.026(6) -0.007(5)
C17 0.070(8) 0.094(9) 0.106(10) -0.055(8) 0.039(8) -0.041(7)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.998(7) . ?
Pd1 N2 2.002(7) . ?
Pd1 O2 2.030(6) . ?
Pd1 O1 2.046(7) . ?
Pd1 Pd1 3.0396(12) 2_756 ?
O1 C1 1.233(13) 2_756 ?
O2 C1 1.275(13) . ?
O3 C7 1.197(12) . ?
N1 C6 1.326(12) . ?
N1 C2 1.332(13) . ?
N2 C7 1.333(12) . ?
N2 C10 1.437(12) . ?
C1 O1 1.233(13) 2_756 ?
C1 C17 1.474(14) . ?
C2 C3 1.401(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.336(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.422(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.484(14) . ?
C10 C15 1.378(14) . ?
C10 C11 1.393(14) . ?
C11 C12 1.378(18) . ?
C11 C16 1.544(18) . ?
C12 C13 1.356(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.424(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.430(15) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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 N2 81.3(3) . . ?
N1 Pd1 O2 172.7(3) . . ?
N2 Pd1 O2 93.4(3) . . ?
N1 Pd1 O1 93.1(3) . . ?
N2 Pd1 O1 173.8(3) . . ?
O2 Pd1 O1 92.0(3) . . ?
N1 Pd1 Pd1 108.6(2) . 2_756 ?
N2 Pd1 Pd1 106.0(2) . 2_756 ?
O2 Pd1 Pd1 77.5(2) . 2_756 ?
O1 Pd1 Pd1 78.3(2) . 2_756 ?
C1 O1 Pd1 127.6(7) 2_756 . ?
C1 O2 Pd1 127.2(6) . . ?
C6 N1 C2 122.6(8) . . ?
C6 N1 Pd1 112.4(6) . . ?
C2 N1 Pd1 125.1(7) . . ?
C7 N2 C10 118.6(8) . . ?
C7 N2 Pd1 116.1(6) . . ?
C10 N2 Pd1 124.7(6) . . ?
O1 C1 O2 125.3(9) 2_756 . ?
O1 C1 C17 118.5(11) 2_756 . ?
O2 C1 C17 116.2(10) . . ?
N1 C2 C3 119.7(10) . . ?
N1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.7(10) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.8(10) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 118.7(11) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N1 C6 C5 119.4(9) . . ?
N1 C6 C7 118.7(8) . . ?
C5 C6 C7 121.8(9) . . ?
O3 C7 N2 129.3(9) . . ?
O3 C7 C6 119.5(8) . . ?
N2 C7 C6 111.2(8) . . ?
C15 C10 C11 123.1(10) . . ?
C15 C10 N2 117.1(9) . . ?
C11 C10 N2 119.8(9) . . ?
C12 C11 C10 118.3(11) . . ?
C12 C11 C16 120.9(10) . . ?
C10 C11 C16 120.8(11) . . ?
C13 C12 C11 122.2(11) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 119.7(10) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 119.5(10) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C14 117.2(10) . . ?
C10 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        68.21
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         5.967
_refine_diff_density_min         -1.187
_refine_diff_density_rms         0.299
_database_code_depnum_ccdc_archive 'CCDC 969094'