# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bip27
_database_code_depnum_ccdc_archive 'CCDC 1062049'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C113.67 H108 Cl11 I12 N24 Pd6'
_chemical_formula_weight         4361.39

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   R-3

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

_cell_length_a                   35.2807(14)
_cell_length_b                   35.2807(14)
_cell_length_c                   10.4598(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11275.3(8)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4102
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.40

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6171
_exptl_absorpt_coefficient_mu    3.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5643
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'Blessing, 1995'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 D8 Venture'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            60558
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         26.40
_reflns_number_total             5059
_reflns_number_gt                4102
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0455P)²+223.0825P] where P=(Fo²+2Fc²)/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         5059
_refine_ls_number_parameters     269
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.002
_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
N4 N 0.6099(2) 0.8522(2) 0.9877(6) 0.0406(15) Uani 1 1 d . . .
C6 C 0.39796(17) 0.75862(17) 0.9918(6) 0.0170(11) Uani 1 1 d . . .
C1 C 0.53870(17) 0.91272(17) 0.9485(6) 0.0189(11) Uani 1 1 d . . .
C5 C 0.43625(19) 0.77267(18) 0.9213(6) 0.0235(13) Uani 1 1 d . . .
H5 H 0.4415 0.7520 0.8828 0.028 Uiso 1 1 calc R . .
C3 C 0.45964(17) 0.84854(17) 0.9637(6) 0.0194(12) Uani 1 1 d . . .
C7 C 0.36485(17) 0.71139(16) 0.9990(6) 0.0170(11) Uani 1 1 d . . .
C2 C 0.49362(17) 0.89462(17) 0.9507(6) 0.0176(11) Uani 1 1 d . . .
C4 C 0.46671(18) 0.81670(18) 0.9073(7) 0.0248(13) Uani 1 1 d . . .
H4 H 0.4920 0.8251 0.8600 0.030 Uiso 1 1 calc R . .
C8 C 0.32035(17) 0.69793(17) 0.9999(5) 0.0161(11) Uani 1 1 d . . .
H8 H 0.3116 0.7188 1.0011 0.019 Uiso 1 1 calc R . .
C17 C 0.39149(17) 0.79056(17) 1.0494(5) 0.0172(11) Uani 1 1 d . . .
H17 H 0.3663 0.7821 1.0971 0.021 Uiso 1 1 calc R . .
C18 C 0.42186(18) 0.83466(17) 1.0369(6) 0.0194(12) Uani 1 1 d . . .
H18 H 0.4170 0.8553 1.0779 0.023 Uiso 1 1 calc R . .
C15 C 0.60020(19) 0.99174(19) 0.9364(7) 0.0298(15) Uani 1 1 d . . .
H15A H 0.6017 1.0176 0.8989 0.036 Uiso 1 1 calc R . .
H15B H 0.6169 0.9830 0.8824 0.036 Uiso 1 1 calc R . .
C14 C 0.4450(2) 0.9296(2) 0.9323(8) 0.0374(18) Uani 1 1 d . . .
H14A H 0.4501 0.9565 0.8942 0.056 Uiso 1 1 calc R . .
H14B H 0.4331 0.9269 1.0165 0.056 Uiso 1 1 calc R . .
H14C H 0.4246 0.9054 0.8807 0.056 Uiso 1 1 calc R . .
C16 C 0.6206(2) 1.0030(2) 1.0667(8) 0.0399(18) Uani 1 1 d . . .
H16A H 0.6505 1.0260 1.0596 0.060 Uiso 1 1 calc R . .
H16B H 0.6196 0.9776 1.1039 0.060 Uiso 1 1 calc R . .
H16C H 0.6047 1.0124 1.1199 0.060 Uiso 1 1 calc R . .
C13 C 0.6533(3) 0.8728(4) 0.9715(8) 0.061(3) Uani 1 1 d . . .
H13 H 0.6684 0.9025 0.9520 0.073 Uiso 1 1 calc R . .
C9 C 0.5897(4) 0.8101(3) 1.0172(8) 0.064(3) Uani 1 1 d . . .
H9 H 0.5595 0.7963 1.0283 0.077 Uiso 1 1 calc R . .
C11 C 0.6513(6) 0.8045(6) 1.0158(10) 0.093(5) Uani 1 1 d . . .
H11 H 0.6652 0.7882 1.0247 0.112 Uiso 1 1 calc R . .
C12 C 0.6765(4) 0.8493(6) 0.9840(9) 0.087(5) Uani 1 1 d . . .
H12 H 0.7066 0.8628 0.9718 0.105 Uiso 1 1 calc R . .
C10 C 0.6087(5) 0.7850(4) 1.0331(10) 0.083(4) Uani 1 1 d . . .
H10 H 0.5924 0.7556 1.0550 0.100 Uiso 1 1 calc R . .
N3 N 0.48644(15) 0.92934(15) 0.9406(5) 0.0218(11) Uani 1 1 d . . .
N1 N 0.55425(15) 0.95631(15) 0.9387(5) 0.0220(11) Uani 1 1 d . . .
N2 N 0.52328(16) 0.96747(15) 0.9351(5) 0.0259(11) Uani 1 1 d . . .
C100 C 0.3333 0.6667 0.6667 0.069(7) Uani 1 6 d S . .
Cl4 Cl 0.3763(4) 0.6543(5) 0.6770(13) 0.120(4) Uani 0.33 1 d PU . .
I1 I 0.550285(13) 0.873477(13) 1.20362(4) 0.02912(12) Uani 1 1 d . . .
Pd1 Pd 0.574141(14) 0.884581(14) 0.96505(5) 0.02137(13) Uani 1 1 d . . .
I2 I 0.591464(15) 0.897587(16) 0.72077(5) 0.03723(14) Uani 1 1 d . . .
Cl10 Cl 0.52924(10) 0.76656(10) 0.7195(3) 0.0611(8) Uani 0.75 1 d PU A .
C50 C 0.5106(8) 0.7116(8) 0.753(2) 0.126(7) Uani 0.75 1 d PU . .
Cl3 Cl 0.49491(15) 0.69767(15) 0.8857(5) 0.0373(10) Uani 0.38 1 d PU A 1
Cl3A Cl 0.4677(2) 0.6744(2) 0.8009(7) 0.0640(16) Uiso 0.38 1 d P A 2


_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
N4 C9 1.324(12) . ?
N4 C13 1.336(11) . ?
N4 Pd1 2.096(6) . ?
C6 C17 1.393(8) . ?
C6 C5 1.394(8) . ?
C6 C7 1.483(7) . ?
C1 N1 1.354(7) . ?
C1 C2 1.387(7) . ?
C1 Pd1 1.954(6) . ?
C5 C4 1.386(8) . ?
C3 C18 1.397(8) . ?
C3 C4 1.398(8) . ?
C3 C2 1.466(7) . ?
C7 C8 1.395(7) . ?
C7 C8 1.399(7) 3_565 ?
C2 N3 1.373(7) . ?
C8 C7 1.399(7) 2_665 ?
C17 C18 1.385(7) . ?
C15 N1 1.471(7) . ?
C15 C16 1.499(10) . ?
C14 N3 1.469(7) . ?
C13 C12 1.436(14) . ?
C9 C10 1.363(13) . ?
C11 C10 1.315(19) . ?
C11 C12 1.41(2) . ?
N3 N2 1.324(7) . ?
N1 N2 1.334(7) . ?
C100 Cl4 1.779(13) 14_456 ?
C100 Cl4 1.779(14) 15_556 ?
C100 Cl4 1.779(13) 2_665 ?
C100 Cl4 1.779(13) 3_565 ?
C100 Cl4 1.779(13) . ?
C100 Cl4 1.779(13) 13_566 ?
Cl4 Cl4 1.789(14) 14_456 ?
Cl4 Cl4 1.789(14) 15_556 ?
I1 Pd1 2.5998(7) . ?
Pd1 I2 2.6138(7) . ?
Cl10 C50 1.74(2) . ?
C50 Cl3 1.48(2) . ?
C50 Cl3A 1.51(2) . ?

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
C9 N4 C13 118.0(8) . . ?
C9 N4 Pd1 120.2(6) . . ?
C13 N4 Pd1 121.7(6) . . ?
C17 C6 C5 117.5(5) . . ?
C17 C6 C7 122.1(5) . . ?
C5 C6 C7 120.3(5) . . ?
N1 C1 C2 104.1(5) . . ?
N1 C1 Pd1 125.8(4) . . ?
C2 C1 Pd1 130.0(4) . . ?
C4 C5 C6 121.7(5) . . ?
C18 C3 C4 118.2(5) . . ?
C18 C3 C2 123.2(5) . . ?
C4 C3 C2 118.5(5) . . ?
C8 C7 C8 119.0(5) . 3_565 ?
C8 C7 C6 120.2(5) . . ?
C8 C7 C6 120.8(5) 3_565 . ?
N3 C2 C1 105.6(5) . . ?
N3 C2 C3 125.7(5) . . ?
C1 C2 C3 128.7(5) . . ?
C5 C4 C3 120.4(5) . . ?
C7 C8 C7 121.0(5) . 2_665 ?
C18 C17 C6 121.4(5) . . ?
C17 C18 C3 120.8(5) . . ?
N1 C15 C16 112.9(5) . . ?
N4 C13 C12 120.2(11) . . ?
N4 C9 C10 126.3(12) . . ?
C10 C11 C12 122.2(10) . . ?
C11 C12 C13 116.5(11) . . ?
C11 C10 C9 116.7(13) . . ?
N2 N3 C2 112.6(4) . . ?
N2 N3 C14 117.8(5) . . ?
C2 N3 C14 129.6(5) . . ?
N2 N1 C1 114.3(4) . . ?
N2 N1 C15 117.8(5) . . ?
C1 N1 C15 127.9(5) . . ?
N3 N2 N1 103.4(4) . . ?
Cl4 C100 Cl4 119.65(10) 14_456 15_556 ?
Cl4 C100 Cl4 179.996(3) 14_456 2_665 ?
Cl4 C100 Cl4 60.36(10) 15_556 2_665 ?
Cl4 C100 Cl4 60.36(10) 14_456 3_565 ?
Cl4 C100 Cl4 179.995(3) 15_556 3_565 ?
Cl4 C100 Cl4 119.64(10) 2_665 3_565 ?
Cl4 C100 Cl4 60.37(10) 14_456 . ?
Cl4 C100 Cl4 60.37(10) 15_556 . ?
Cl4 C100 Cl4 119.64(11) 2_665 . ?
Cl4 C100 Cl4 119.64(10) 3_565 . ?
Cl4 C100 Cl4 119.63(11) 14_456 13_566 ?
Cl4 C100 Cl4 119.63(10) 15_556 13_566 ?
Cl4 C100 Cl4 60.36(10) 2_665 13_566 ?
Cl4 C100 Cl4 60.36(10) 3_565 13_566 ?
Cl4 C100 Cl4 179.998(2) . 13_566 ?
C100 Cl4 Cl4 59.81(4) . 14_456 ?
C100 Cl4 Cl4 59.81(5) . 15_556 ?
Cl4 Cl4 Cl4 118.6(4) 14_456 15_556 ?
C1 Pd1 N4 177.4(3) . . ?
C1 Pd1 I1 85.43(18) . . ?
N4 Pd1 I1 92.70(18) . . ?
C1 Pd1 I2 88.70(18) . . ?
N4 Pd1 I2 93.12(18) . . ?
I1 Pd1 I2 173.92(2) . . ?
Cl3 C50 Cl3A 49.9(9) . . ?
Cl3 C50 Cl10 115.4(15) . . ?
Cl3A C50 Cl10 133.8(16) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         2.386
_refine_diff_density_min         -0.982
_refine_diff_density_rms         0.153
