# Electronic Supplementary Material (ESI) for RSC Advances.
# 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/. 
# 
# 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_d100
_database_code_depnum_ccdc_archive 'CCDC 1031688'
_audit_update_record             
;
2014-10-30 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H35 Cl2 N5 Pd'
_chemical_formula_weight         558.86

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.8954(5)
_cell_length_b                   13.9545(6)
_cell_length_c                   17.7018(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.7110(10)
_cell_angle_gamma                90.00
_cell_volume                     2427.61(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6714
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    1.005
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5022
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16817
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5558
_reflns_number_gt                5120
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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. 
;

_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)+(0.0318P)²+2.4697P] where P=(Fo²+2Fc²)/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         5558
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.623298(17) -0.143091(13) 0.090127(10) 0.01299(7) Uani 1 1 d . . .
Cl1 Cl 0.39862(6) -0.16908(5) 0.09949(4) 0.02641(15) Uani 1 1 d . . .
Cl2 Cl 0.60129(7) -0.19006(5) -0.03441(3) 0.02467(14) Uani 1 1 d . . .
N1 N 0.64948(19) -0.10521(15) 0.20126(11) 0.0146(4) Uani 1 1 d . . .
N2 N 0.6497(2) -0.01319(14) 0.22667(11) 0.0159(4) Uani 1 1 d . . .
N3 N 0.8237(2) -0.11952(14) 0.08662(11) 0.0139(4) Uani 1 1 d . . .
N4 N 0.8789(2) -0.02959(14) 0.08959(11) 0.0153(4) Uani 1 1 d . . .
N5 N 0.7458(2) 0.10053(15) 0.14008(12) 0.0173(4) Uani 1 1 d . . .
C1 C 0.6643(2) -0.16223(18) 0.26219(15) 0.0181(5) Uani 1 1 d . . .
C2 C 0.6743(3) -0.1059(2) 0.32768(14) 0.0207(5) Uani 1 1 d . . .
H2 H 0.6856 -0.1281 0.3788 0.025 Uiso 1 1 calc R . .
C3 C 0.6645(2) -0.0120(2) 0.30380(14) 0.0204(5) Uani 1 1 d . . .
C4 C 0.6674(3) -0.26819(19) 0.25479(15) 0.0227(5) Uani 1 1 d . . .
H4A H 0.5958 -0.2887 0.2152 0.034 Uiso 1 1 calc R . .
H4B H 0.6523 -0.2976 0.3034 0.034 Uiso 1 1 calc R . .
H4C H 0.7563 -0.2881 0.2410 0.034 Uiso 1 1 calc R . .
C5 C 0.6658(3) 0.0775(2) 0.34973(16) 0.0320(7) Uani 1 1 d . . .
H5A H 0.7571 0.1058 0.3545 0.048 Uiso 1 1 calc R . .
H5B H 0.6412 0.0625 0.4004 0.048 Uiso 1 1 calc R . .
H5C H 0.6001 0.1232 0.3245 0.048 Uiso 1 1 calc R . .
C6 C 0.6292(2) 0.06714(17) 0.17161(14) 0.0178(5) Uani 1 1 d . . .
H6A H 0.5609 0.0469 0.1293 0.021 Uiso 1 1 calc R . .
H6B H 0.5897 0.1217 0.1973 0.021 Uiso 1 1 calc R . .
C7 C 0.9249(3) -0.18201(18) 0.08822(13) 0.0166(5) Uani 1 1 d . . .
C8 C 1.0489(3) -0.13209(18) 0.09169(14) 0.0193(5) Uani 1 1 d . . .
H8 H 1.1372 -0.1593 0.0934 0.023 Uiso 1 1 calc R . .
C9 C 1.0174(2) -0.03633(19) 0.09205(13) 0.0173(5) Uani 1 1 d . . .
C10 C 0.9012(3) -0.28709(18) 0.08708(16) 0.0230(6) Uani 1 1 d . . .
H10A H 0.9270 -0.3134 0.1381 0.035 Uiso 1 1 calc R . .
H10B H 0.9562 -0.3172 0.0511 0.035 Uiso 1 1 calc R . .
H10C H 0.8047 -0.3000 0.0714 0.035 Uiso 1 1 calc R . .
C11 C 1.1108(3) 0.0480(2) 0.09491(14) 0.0216(5) Uani 1 1 d . . .
H11A H 1.0734 0.0961 0.0578 0.032 Uiso 1 1 calc R . .
H11B H 1.2004 0.0274 0.0827 0.032 Uiso 1 1 calc R . .
H11C H 1.1197 0.0759 0.1461 0.032 Uiso 1 1 calc R . .
C12 C 0.7893(2) 0.05510(17) 0.07533(13) 0.0162(5) Uani 1 1 d . . .
H12A H 0.8378 0.1032 0.0474 0.019 Uiso 1 1 calc R . .
H12B H 0.7074 0.0352 0.0414 0.019 Uiso 1 1 calc R . .
C13 C 0.8422(3) 0.16454(18) 0.18448(14) 0.0185(5) Uani 1 1 d . . .
H13A H 0.9357 0.1419 0.1801 0.022 Uiso 1 1 calc R . .
H13B H 0.8273 0.1599 0.2387 0.022 Uiso 1 1 calc R . .
C14 C 0.8316(2) 0.27064(18) 0.16031(14) 0.0176(5) Uani 1 1 d . . .
C15 C 0.6959(3) 0.31444(19) 0.17713(16) 0.0219(5) Uani 1 1 d . . .
H15A H 0.6196 0.2809 0.1469 0.026 Uiso 1 1 calc R . .
H15B H 0.6854 0.3061 0.2317 0.026 Uiso 1 1 calc R . .
C16 C 0.6916(3) 0.4213(2) 0.15713(17) 0.0264(6) Uani 1 1 d . . .
H16 H 0.6033 0.4493 0.1688 0.032 Uiso 1 1 calc R . .
C17 C 0.7041(3) 0.4334(2) 0.07264(16) 0.0264(6) Uani 1 1 d . . .
H17A H 0.6994 0.5022 0.0590 0.032 Uiso 1 1 calc R . .
H17B H 0.6280 0.4000 0.0422 0.032 Uiso 1 1 calc R . .
C18 C 0.8400(3) 0.3914(2) 0.05477(16) 0.0240(6) Uani 1 1 d . . .
H18 H 0.8485 0.3994 -0.0006 0.029 Uiso 1 1 calc R . .
C19 C 0.8441(3) 0.28417(18) 0.07515(14) 0.0188(5) Uani 1 1 d . . .
H19A H 0.7684 0.2505 0.0445 0.023 Uiso 1 1 calc R . .
H19B H 0.9308 0.2560 0.0630 0.023 Uiso 1 1 calc R . .
C20 C 0.8089(3) 0.4725(2) 0.20417(18) 0.0309(6) Uani 1 1 d . . .
H20A H 0.8003 0.4645 0.2590 0.037 Uiso 1 1 calc R . .
H20B H 0.8052 0.5419 0.1924 0.037 Uiso 1 1 calc R . .
C21 C 0.9455(3) 0.4312(2) 0.18659(17) 0.0275(6) Uani 1 1 d . . .
H21 H 1.0220 0.4653 0.2174 0.033 Uiso 1 1 calc R . .
C22 C 0.9581(3) 0.44329(19) 0.10217(17) 0.0280(6) Uani 1 1 d . . .
H22A H 1.0459 0.4164 0.0905 0.034 Uiso 1 1 calc R . .
H22B H 0.9563 0.5123 0.0890 0.034 Uiso 1 1 calc R . .
C23 C 0.9499(3) 0.3241(2) 0.20617(15) 0.0238(6) Uani 1 1 d . . .
H23A H 0.9440 0.3157 0.2612 0.029 Uiso 1 1 calc R . .
H23B H 1.0374 0.2966 0.1947 0.029 Uiso 1 1 calc R . .


_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 N3 2.019(2) . ?
Pd1 N1 2.024(2) . ?
Pd1 Cl1 2.2777(6) . ?
Pd1 Cl2 2.2858(6) . ?
N1 C1 1.334(3) . ?
N1 N2 1.361(3) . ?
N2 C3 1.356(3) . ?
N2 C6 1.484(3) . ?
N3 C7 1.326(3) . ?
N3 N4 1.367(3) . ?
N4 C9 1.369(3) . ?
N4 C12 1.481(3) . ?
N5 C6 1.418(3) . ?
N5 C12 1.420(3) . ?
N5 C13 1.467(3) . ?
C1 C2 1.394(4) . ?
C1 C4 1.485(4) . ?
C2 C3 1.377(4) . ?
C3 C5 1.490(4) . ?
C7 C8 1.405(4) . ?
C7 C10 1.485(3) . ?
C8 C9 1.372(4) . ?
C9 C11 1.493(3) . ?
C13 C14 1.541(3) . ?
C14 C15 1.536(3) . ?
C14 C23 1.538(3) . ?
C14 C19 1.539(3) . ?
C15 C16 1.533(4) . ?
C16 C17 1.524(4) . ?
C16 C20 1.525(4) . ?
C17 C18 1.533(4) . ?
C18 C22 1.538(4) . ?
C18 C19 1.539(4) . ?
C20 C21 1.535(4) . ?
C21 C22 1.523(4) . ?
C21 C23 1.534(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
N3 Pd1 N1 88.44(8) . . ?
N3 Pd1 Cl1 177.60(6) . . ?
N1 Pd1 Cl1 89.20(6) . . ?
N3 Pd1 Cl2 90.01(6) . . ?
N1 Pd1 Cl2 177.62(6) . . ?
Cl1 Pd1 Cl2 92.33(3) . . ?
C1 N1 N2 107.4(2) . . ?
C1 N1 Pd1 128.26(18) . . ?
N2 N1 Pd1 124.25(15) . . ?
C3 N2 N1 109.9(2) . . ?
C3 N2 C6 130.0(2) . . ?
N1 N2 C6 120.07(19) . . ?
C7 N3 N4 107.79(19) . . ?
C7 N3 Pd1 129.39(17) . . ?
N4 N3 Pd1 122.54(15) . . ?
N3 N4 C9 109.4(2) . . ?
N3 N4 C12 119.81(19) . . ?
C9 N4 C12 129.6(2) . . ?
C6 N5 C12 120.6(2) . . ?
C6 N5 C13 119.8(2) . . ?
C12 N5 C13 117.7(2) . . ?
N1 C1 C2 109.1(2) . . ?
N1 C1 C4 121.6(2) . . ?
C2 C1 C4 129.3(2) . . ?
C3 C2 C1 106.6(2) . . ?
N2 C3 C2 107.0(2) . . ?
N2 C3 C5 123.5(2) . . ?
C2 C3 C5 129.4(2) . . ?
N5 C6 N2 116.8(2) . . ?
N3 C7 C8 109.1(2) . . ?
N3 C7 C10 122.1(2) . . ?
C8 C7 C10 128.7(2) . . ?
C9 C8 C7 106.6(2) . . ?
N4 C9 C8 107.1(2) . . ?
N4 C9 C11 124.0(2) . . ?
C8 C9 C11 128.9(2) . . ?
N5 C12 N4 116.8(2) . . ?
N5 C13 C14 114.7(2) . . ?
C15 C14 C23 109.5(2) . . ?
C15 C14 C19 108.3(2) . . ?
C23 C14 C19 108.3(2) . . ?
C15 C14 C13 111.2(2) . . ?
C23 C14 C13 107.2(2) . . ?
C19 C14 C13 112.3(2) . . ?
C16 C15 C14 110.1(2) . . ?
C17 C16 C20 109.9(2) . . ?
C17 C16 C15 109.3(2) . . ?
C20 C16 C15 109.3(2) . . ?
C16 C17 C18 109.5(2) . . ?
C17 C18 C22 109.7(2) . . ?
C17 C18 C19 108.8(2) . . ?
C22 C18 C19 109.4(2) . . ?
C14 C19 C18 110.3(2) . . ?
C16 C20 C21 110.3(2) . . ?
C22 C21 C23 109.0(2) . . ?
C22 C21 C20 109.4(2) . . ?
C23 C21 C20 108.8(2) . . ?
C21 C22 C18 109.8(2) . . ?
C21 C23 C14 110.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.093
