# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_p

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 Cl4 N4 Pd2 S2'
_chemical_formula_weight         667.09

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'
Cl Cl 0.1484 0.1585 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P-421c

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

_cell_length_a                   10.954(3)
_cell_length_b                   10.954
_cell_length_c                   19.840(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2380.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1360
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      18.93

_exptl_crystal_description       noddle-like
_exptl_crystal_colour            red-brown
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    2.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8473
_exptl_absorpt_correction_T_max  0.8822
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_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            10996
_diffrn_reflns_av_R_equivalents  0.1138
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2099
_reflns_number_gt                1218
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Olex2
_computing_publication_material  Olex2

_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 > 2sigma(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. 

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C6
 1.5 with sigma of 0.001
3. Rigid bond restraints
 C6, C7
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C5 ∼ C4A: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
C2 ∼ C3: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
C6 ∼ C7: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
C6 ∼ C7 ∼ N2: within 1.7A with sigma of 0.005 and sigma for terminal
atoms of 0.08
5.a Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C6(H6A,H6B)
5.b Me refined with riding coordinates:
 C7(H7A,H7B,H7C)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;

_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)+(0.0306P)²+14.1443P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(12)
_refine_ls_number_reflns         2099
_refine_ls_number_parameters     119
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.087
_refine_ls_shift/su_mean         0.007

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 -0.05475(9) 0.13886(9) -0.60643(5) 0.0502(3) Uani 1 1 d . . .
Cl1 Cl -0.2493(3) 0.2098(3) -0.6303(2) 0.0754(13) Uani 1 1 d . . .
Cl2 Cl 0.0376(4) 0.3221(3) -0.6308(2) 0.0812(12) Uani 1 1 d . . .
S1 S -0.1273(3) -0.0516(3) -0.57642(14) 0.0515(8) Uani 1 1 d . . .
C1 C -0.2457(10) -0.0948(11) -0.6309(8) 0.054(4) Uani 1 1 d . . .
C2 C -0.4322(14) -0.1514(16) -0.6599(8) 0.084(4) Uani 1 1 d U . .
H2 H -0.5125 -0.1782 -0.6569 0.101 Uiso 1 1 calc R . .
C3 C -0.3730(14) -0.1280(16) -0.7155(9) 0.081(4) Uani 1 1 d U . .
H3 H -0.4040 -0.1335 -0.7590 0.097 Uiso 1 1 calc R . .
C4A C -0.1561(16) -0.0652(17) -0.7447(7) 0.087(5) Uani 1 1 d U . .
H4AA H -0.1275 -0.1399 -0.7657 0.105 Uiso 1 1 calc R . .
H4AB H -0.0885 -0.0297 -0.7199 0.105 Uiso 1 1 calc R . .
C5 C -0.198(2) 0.0236(17) -0.7990(8) 0.133(9) Uani 1 1 d U . .
H5A H -0.1361 0.0297 -0.8332 0.200 Uiso 1 1 calc R . .
H5B H -0.2112 0.1025 -0.7792 0.200 Uiso 1 1 calc R . .
H5C H -0.2723 -0.0053 -0.8187 0.200 Uiso 1 1 calc R . .
C6 C -0.3866(15) -0.1402(16) -0.5347(8) 0.097(4) Uani 1 1 d DU . .
H6A H -0.4524 -0.0840 -0.5243 0.116 Uiso 1 1 calc R . .
H6B H -0.3166 -0.1179 -0.5074 0.116 Uiso 1 1 calc R . .
C7 C -0.426(3) -0.2677(18) -0.5172(12) 0.233(15) Uani 1 1 d DU . .
H7A H -0.4465 -0.2716 -0.4703 0.350 Uiso 1 1 calc R . .
H7B H -0.3597 -0.3232 -0.5263 0.350 Uiso 1 1 calc R . .
H7C H -0.4952 -0.2898 -0.5439 0.350 Uiso 1 1 calc R . .
N1 N -0.2563(11) -0.0936(10) -0.6980(6) 0.058(3) Uani 1 1 d . . .
N2 N -0.3548(11) -0.1294(12) -0.6063(8) 0.090(3) Uani 1 1 d U . .

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 0.0357(6) 0.0617(7) 0.0533(5) -0.0041(7) -0.0011(6) -0.0034(5)
Cl1 0.047(2) 0.076(3) 0.104(4) 0.003(2) -0.004(2) 0.0075(19)
Cl2 0.073(3) 0.065(3) 0.106(3) 0.016(2) -0.005(2) -0.008(2)
S1 0.036(2) 0.073(2) 0.0458(15) -0.0030(18) 0.0006(16) -0.011(2)
C1 0.021(7) 0.052(9) 0.088(12) -0.007(7) 0.003(7) -0.007(5)
C2 0.039(8) 0.104(10) 0.109(11) -0.028(10) -0.020(7) -0.010(8)
C3 0.039(8) 0.100(10) 0.102(11) -0.027(10) -0.023(7) -0.009(7)
C4A 0.084(13) 0.118(15) 0.059(8) -0.006(10) 0.005(9) -0.004(12)
C5 0.22(3) 0.089(16) 0.094(13) 0.020(11) -0.006(15) 0.052(15)
C6 0.063(7) 0.129(9) 0.098(8) -0.025(10) 0.007(8) -0.023(8)
C7 0.34(4) 0.23(3) 0.131(18) 0.05(2) -0.05(3) -0.10(3)
N1 0.061(8) 0.062(9) 0.052(7) -0.004(6) -0.005(6) 0.002(6)
N2 0.059(7) 0.119(9) 0.093(7) -0.023(9) 0.005(8) -0.023(7)

_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 S1 2.290(4) 3 ?
Pd1 Cl2 2.299(4) . ?
Pd1 S1 2.311(4) . ?
Pd1 Cl1 2.317(4) . ?
S1 C1 1.753(13) . ?
S1 Pd1 2.290(4) 3 ?
C1 N1 1.335(15) . ?
C1 N2 1.345(15) . ?
C2 C3 1.30(2) . ?
C2 N2 1.382(18) . ?
C2 H2 0.9300 . ?
C3 N1 1.377(18) . ?
C3 H3 0.9300 . ?
C4A N1 1.471(17) . ?
C4A C5 1.52(2) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N2 1.47(2) . ?
C6 C7 1.4998(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
S1 Pd1 Cl2 92.04(14) 3 . ?
S1 Pd1 S1 81.72(13) 3 . ?
Cl2 Pd1 S1 173.62(14) . . ?
S1 Pd1 Cl1 173.66(13) 3 . ?
Cl2 Pd1 Cl1 93.97(14) . . ?
S1 Pd1 Cl1 92.22(13) . . ?
C1 S1 Pd1 111.8(5) . 3 ?
C1 S1 Pd1 109.8(5) . . ?
Pd1 S1 Pd1 90.58(11) 3 . ?
N1 C1 N2 106.7(12) . . ?
N1 C1 S1 132.5(10) . . ?
N2 C1 S1 120.6(12) . . ?
C3 C2 N2 108.2(15) . . ?
C3 C2 H2 125.9 . . ?
N2 C2 H2 125.9 . . ?
C2 C3 N1 107.6(15) . . ?
C2 C3 H3 126.2 . . ?
N1 C3 H3 126.2 . . ?
N1 C4A C5 111.0(15) . . ?
N1 C4A H4AA 109.4 . . ?
C5 C4A H4AA 109.4 . . ?
N1 C4A H4AB 109.4 . . ?
C5 C4A H4AB 109.5 . . ?
H4AA C4A H4AB 108.0 . . ?
C4A C5 H5A 109.5 . . ?
C4A C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4A C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 111.5(16) . . ?
N2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 N1 C3 109.2(13) . . ?
C1 N1 C4A 124.5(12) . . ?
C3 N1 C4A 126.3(12) . . ?
C1 N2 C2 108.3(15) . . ?
C1 N2 C6 125.8(14) . . ?
C2 N2 C6 125.9(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 Pd1 S1 C1 -142.7(5) 3 . . . ?
Cl2 Pd1 S1 C1 -154.7(13) . . . . ?
Cl1 Pd1 S1 C1 39.1(5) . . . . ?
S1 Pd1 S1 Pd1 -29.25(15) 3 . . 3 ?
Cl2 Pd1 S1 Pd1 -41.2(13) . . . 3 ?
Cl1 Pd1 S1 Pd1 152.61(12) . . . 3 ?
Pd1 S1 C1 N1 -51.0(14) 3 . . . ?
Pd1 S1 C1 N1 47.9(14) . . . . ?
Pd1 S1 C1 N2 134.6(11) 3 . . . ?
Pd1 S1 C1 N2 -126.5(11) . . . . ?
N2 C2 C3 N1 1(2) . . . . ?
N2 C1 N1 C3 -0.1(16) . . . . ?
S1 C1 N1 C3 -175.0(12) . . . . ?
N2 C1 N1 C4A -177.5(14) . . . . ?
S1 C1 N1 C4A 8(2) . . . . ?
C2 C3 N1 C1 -0.9(19) . . . . ?
C2 C3 N1 C4A 176.5(16) . . . . ?
C5 C4A N1 C1 -134.0(15) . . . . ?
C5 C4A N1 C3 49(2) . . . . ?
N1 C1 N2 C2 0.9(17) . . . . ?
S1 C1 N2 C2 176.6(10) . . . . ?
N1 C1 N2 C6 -178.2(14) . . . . ?
S1 C1 N2 C6 -3(2) . . . . ?
C3 C2 N2 C1 -1(2) . . . . ?
C3 C2 N2 C6 177.7(16) . . . . ?
C7 C6 N2 C1 -121(2) . . . . ?
C7 C6 N2 C2 60(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.136
_database_code_depnum_ccdc_archive 'CCDC 994393'
