# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1810954'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C24 H16 N4 Pd, 2(N O3) '
_chemical_formula_sum            'C24 H16 N6 O6 Pd'
_chemical_formula_weight         590.83

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   15.031(3)
_cell_length_b                   20.228(3)
_cell_length_c                   7.1314(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.038(6)
_cell_angle_gamma                90
_cell_volume                     2112.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    9093
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.14
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.939
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6374
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   Bruker

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_number            49525
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.326
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2627
_reflns_number_gt                2456
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'SAINT(Bruker, 2013)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²+8.0843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2627
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3895(3) 0.09362(15) 0.1516(5) 0.0436(7) Uani 1 1 d . . . . .
H1 H 0.4428 0.0732 0.1360 0.052 Uiso 1 1 calc R U . . .
C2 C 0.3079(3) 0.05724(17) 0.1177(5) 0.0549(9) Uani 1 1 d . . . . .
H2 H 0.3081 0.0130 0.0818 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2285(3) 0.08575(18) 0.1366(5) 0.0516(9) Uani 1 1 d . . . . .
H3 H 0.1750 0.0610 0.1183 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2283(2) 0.15331(16) 0.1842(4) 0.0390(7) Uani 1 1 d . . . . .
C5 C 0.1488(2) 0.18923(19) 0.2015(4) 0.0451(8) Uani 1 1 d . . . . .
H5 H 0.0930 0.1674 0.1815 0.054 Uiso 1 1 calc R U . . .
C6 C 0.1530(2) 0.25402(19) 0.2461(4) 0.0426(7) Uani 1 1 d . . . . .
H6 H 0.1001 0.2762 0.2567 0.051 Uiso 1 1 calc R U . . .
C7 C 0.23763(18) 0.28931(15) 0.2775(4) 0.0329(6) Uani 1 1 d . . . . .
C8 C 0.24775(19) 0.35617(15) 0.3329(4) 0.0363(6) Uani 1 1 d . . . . .
H8 H 0.1972 0.3809 0.3455 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3323(2) 0.38446(14) 0.3678(4) 0.0349(6) Uani 1 1 d . . . . .
H9 H 0.3402 0.4279 0.4107 0.042 Uiso 1 1 calc R U . . .
C10 C 0.40707(17) 0.34786(13) 0.3389(4) 0.0291(5) Uani 1 1 d . . . . .
H10 H 0.4641 0.3680 0.3620 0.035 Uiso 1 1 calc R U . . .
C11 C 0.31624(16) 0.25544(13) 0.2569(3) 0.0265(5) Uani 1 1 d . . . . .
C12 C 0.31215(18) 0.18668(13) 0.2153(4) 0.0300(5) Uani 1 1 d . . . . .
N1 N 0.39231(16) 0.15666(11) 0.2057(3) 0.0322(5) Uani 1 1 d . . . . .
N2 N 0.39971(14) 0.28535(10) 0.2797(3) 0.0248(4) Uani 1 1 d . . . . .
N3 N 0.5000 0.0889(2) 0.7500 0.0524(10) Uani 1 2 d S T P . .
N4 N 0.5000 0.51634(17) 0.2500 0.0333(7) Uani 1 2 d S T P . .
O1 O 0.5266(6) 0.1253(5) 0.8755(10) 0.173(4) Uani 0.75 1 d . . P . .
O2 O 0.5543(5) 0.0532(5) 0.825(2) 0.219(6) Uani 0.75 1 d . . P . .
O3 O 0.43279(19) 0.48560(14) 0.1588(4) 0.0620(8) Uani 1 1 d . . . . .
O4 O 0.5000 0.57752(16) 0.2500 0.0552(9) Uani 1 2 d S T P . .
Pd1 Pd 0.5000 0.22079(2) 0.2500 0.02662(10) Uani 1 2 d S T P . .


_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
C1 N1 1.330(4) . ?
C1 C2 1.405(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.408(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.402(4) . ?
C4 C5 1.428(5) . ?
C5 C6 1.347(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.432(4) . ?
C6 H6 0.9300 . ?
C7 C11 1.402(4) . ?
C7 C8 1.407(4) . ?
C8 C9 1.364(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.400(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.330(3) . ?
C10 H10 0.9300 . ?
C11 N2 1.369(3) . ?
C11 C12 1.421(4) . ?
C12 N1 1.365(4) . ?
N1 Pd1 2.042(2) . ?
N2 Pd1 2.041(2) . ?
N3 O2 1.129(7) 2_656 ?
N3 O2 1.129(7) . ?
N3 O1 1.159(6) . ?
N3 O1 1.159(6) 2_656 ?
N4 O4 1.238(5) . ?
N4 O3 1.238(3) . ?
N4 O3 1.238(3) 2_655 ?
O1 O2 1.580(13) . ?
O1 O1 1.788(15) 2_656 ?
O2 O2 1.740(18) 2_656 ?
Pd1 N2 2.041(2) 2_655 ?
Pd1 N1 2.043(2) 2_655 ?

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 C1 C2 121.4(3) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C12 C4 C3 117.1(3) . . ?
C12 C4 C5 118.8(3) . . ?
C3 C4 C5 124.2(3) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C11 C7 C8 117.3(2) . . ?
C11 C7 C6 118.7(3) . . ?
C8 C7 C6 124.0(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N2 C10 C9 122.5(2) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
N2 C11 C7 122.9(2) . . ?
N2 C11 C12 116.9(2) . . ?
C7 C11 C12 120.2(2) . . ?
N1 C12 C4 123.4(3) . . ?
N1 C12 C11 116.7(2) . . ?
C4 C12 C11 120.0(3) . . ?
C1 N1 C12 118.1(3) . . ?
C1 N1 Pd1 128.7(2) . . ?
C12 N1 Pd1 112.80(17) . . ?
C10 N2 C11 117.8(2) . . ?
C10 N2 Pd1 129.11(17) . . ?
C11 N2 Pd1 112.54(17) . . ?
O2 N3 O2 100.7(13) 2_656 . ?
O2 N3 O1 149.1(7) 2_656 . ?
O2 N3 O1 87.3(8) . . ?
O2 N3 O1 87.3(8) 2_656 2_656 ?
O2 N3 O1 149.1(7) . 2_656 ?
O1 N3 O1 101.0(12) . 2_656 ?
O4 N4 O3 120.1(2) . . ?
O4 N4 O3 120.1(2) . 2_655 ?
O3 N4 O3 119.7(4) . 2_655 ?
N3 O1 O2 45.6(5) . . ?
O2 O1 O1 81.6(6) . 2_656 ?
N3 O2 O1 47.1(5) . . ?
O1 O2 O2 83.1(5) . 2_656 ?
N2 Pd1 N2 100.45(11) . 2_655 ?
N2 Pd1 N1 81.04(9) . . ?
N2 Pd1 N1 165.53(9) 2_655 . ?
N2 Pd1 N1 165.53(9) . 2_655 ?
N2 Pd1 N1 81.05(9) 2_655 2_655 ?
N1 Pd1 N1 101.15(14) . 2_655 ?

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
N1 C1 C2 C3 0.9(5) . . . . ?
C1 C2 C3 C4 2.3(5) . . . . ?
C2 C3 C4 C12 -2.0(5) . . . . ?
C2 C3 C4 C5 177.7(3) . . . . ?
C12 C4 C5 C6 0.2(4) . . . . ?
C3 C4 C5 C6 -179.5(3) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C11 1.3(4) . . . . ?
C5 C6 C7 C8 -177.0(3) . . . . ?
C11 C7 C8 C9 -1.4(4) . . . . ?
C6 C7 C8 C9 177.0(3) . . . . ?
C7 C8 C9 C10 3.2(4) . . . . ?
C8 C9 C10 N2 -0.7(4) . . . . ?
C8 C7 C11 N2 -3.0(4) . . . . ?
C6 C7 C11 N2 178.5(2) . . . . ?
C8 C7 C11 C12 175.3(2) . . . . ?
C6 C7 C11 C12 -3.2(4) . . . . ?
C3 C4 C12 N1 -1.5(4) . . . . ?
C5 C4 C12 N1 178.8(3) . . . . ?
C3 C4 C12 C11 177.7(3) . . . . ?
C5 C4 C12 C11 -2.0(4) . . . . ?
N2 C11 C12 N1 1.2(3) . . . . ?
C7 C11 C12 N1 -177.2(2) . . . . ?
N2 C11 C12 C4 -178.0(2) . . . . ?
C7 C11 C12 C4 3.6(4) . . . . ?
C2 C1 N1 C12 -4.2(4) . . . . ?
C2 C1 N1 Pd1 -176.6(2) . . . . ?
C4 C12 N1 C1 4.6(4) . . . . ?
C11 C12 N1 C1 -174.6(2) . . . . ?
C4 C12 N1 Pd1 178.1(2) . . . . ?
C11 C12 N1 Pd1 -1.1(3) . . . . ?
C9 C10 N2 C11 -3.6(4) . . . . ?
C9 C10 N2 Pd1 -174.3(2) . . . . ?
C7 C11 N2 C10 5.5(4) . . . . ?
C12 C11 N2 C10 -172.9(2) . . . . ?
C7 C11 N2 Pd1 177.72(19) . . . . ?
C12 C11 N2 Pd1 -0.7(3) . . . . ?
O2 N3 O1 O2 107(2) 2_656 . . . ?
O1 N3 O1 O2 -150.0(6) 2_656 . . . ?
O2 N3 O1 O1 -103(2) 2_656 . . 2_656 ?
O2 N3 O1 O1 150.0(6) . . . 2_656 ?
O2 N3 O2 O1 -150.0(7) 2_656 . . . ?
O1 N3 O2 O1 107(2) 2_656 . . . ?
O1 N3 O2 O2 150.0(7) . . . 2_656 ?
O1 N3 O2 O2 -103.0(18) 2_656 . . 2_656 ?
O1 O1 O2 N3 -18.7(5) 2_656 . . . ?
N3 O1 O2 O2 -18.8(6) . . . 2_656 ?
O1 O1 O2 O2 -37.5(8) 2_656 . . 2_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O2 0.93 2.57 3.082(10) 115.0 5_656
C2 H2 O2 0.93 2.43 3.011(9) 120.8 5_656

_refine_diff_density_max         0.835
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.101

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1810955'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N3 O3 Pd, N O3, H2 O'
_chemical_formula_sum            'C21 H20 N4 O7 Pd'
_chemical_formula_weight         546.81

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.6375(19)
_cell_length_b                   22.698(5)
_cell_length_c                   10.034(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.171(6)
_cell_angle_gamma                90
_cell_volume                     2108.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    9787
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.11
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.934
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_T_max  0.7166
_exptl_absorpt_process_details   Bruker

_exptl_special_details           
;
 ?
;


_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_number            49452
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.840
_diffrn_reflns_theta_max         26.467
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4286
_reflns_number_gt                3732
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'SAINT(Bruker, 2013)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+13.2398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4286
_refine_ls_number_parameters     310
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_restrained_S_all      1.254
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6169(7) 0.3938(3) 0.3171(6) 0.0391(14) Uani 1 1 d . . . . .
H1 H 0.5683 0.3670 0.3580 0.047 Uiso 1 1 calc R U . . .
C2 C 0.7297(8) 0.4267(3) 0.4013(7) 0.0495(17) Uani 1 1 d . . . . .
H2 H 0.7544 0.4222 0.4972 0.059 Uiso 1 1 calc R U . . .
C3 C 0.8045(8) 0.4658(3) 0.3430(7) 0.0523(18) Uani 1 1 d . . . . .
H3 H 0.8804 0.4874 0.3993 0.063 Uiso 1 1 calc R U . . .
C4 C 0.7663(7) 0.4731(3) 0.1985(7) 0.0434(15) Uani 1 1 d . . . . .
C5 C 0.8360(8) 0.5114(3) 0.1242(9) 0.0587(19) Uani 1 1 d . . . . .
H5 H 0.9134 0.5342 0.1737 0.070 Uiso 1 1 calc R U . . .
C6 C 0.7934(8) 0.5156(3) -0.0147(9) 0.0570(19) Uani 1 1 d . . . . .
H6 H 0.8403 0.5418 -0.0587 0.068 Uiso 1 1 calc R U . . .
C7 C 0.6775(7) 0.4806(3) -0.0965(7) 0.0434(15) Uani 1 1 d . . . . .
C8 C 0.6286(8) 0.4802(3) -0.2420(7) 0.0514(17) Uani 1 1 d . . . . .
H8 H 0.6715 0.5048 -0.2931 0.062 Uiso 1 1 calc R U . . .
C9 C 0.5188(8) 0.4440(3) -0.3085(7) 0.0489(16) Uani 1 1 d . . . . .
H9 H 0.4872 0.4437 -0.4049 0.059 Uiso 1 1 calc R U . . .
C10 C 0.4533(7) 0.4071(3) -0.2319(6) 0.0414(14) Uani 1 1 d . . . . .
H10 H 0.3783 0.3825 -0.2784 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6070(6) 0.4423(2) -0.0259(6) 0.0331(12) Uani 1 1 d . . . . .
C12 C 0.6501(6) 0.4386(3) 0.1211(6) 0.0351(13) Uani 1 1 d . . . . .
C13 C 0.2010(7) 0.2738(3) -0.0696(6) 0.0382(13) Uani 1 1 d . . . . .
C15 C 0.1678(10) 0.2174(4) 0.1386(8) 0.073(3) Uani 1 1 d . . . . .
H15A H 0.1898 0.1822 0.0935 0.087 Uiso 1 1 calc DR U . A 1
H15B H 0.0634 0.2211 0.1129 0.087 Uiso 1 1 calc DR U . A 1
C16 C 0.2181(7) 0.2070(3) 0.2929(7) 0.0430(15) Uani 1 1 d . . . . .
C17 C 0.1630(8) 0.2377(3) 0.3850(9) 0.061(2) Uani 1 1 d . . . . .
H17 H 0.0914 0.2658 0.3513 0.073 Uiso 1 1 calc R U . . .
C18 C 0.2119(12) 0.2278(4) 0.5273(10) 0.080(3) Uani 1 1 d . . . . .
H18 H 0.1762 0.2499 0.5885 0.096 Uiso 1 1 calc R U . . .
C19 C 0.3137(11) 0.1847(5) 0.5761(8) 0.073(3) Uani 1 1 d . . . . .
C20 C 0.3682(8) 0.1545(4) 0.4884(9) 0.065(2) Uani 1 1 d . . . . .
H20 H 0.4382 0.1258 0.5220 0.078 Uiso 1 1 calc R U . . .
C21 C 0.3206(8) 0.1657(3) 0.3473(8) 0.0530(18) Uani 1 1 d . . . . .
H21 H 0.3601 0.1443 0.2878 0.064 Uiso 1 1 calc R U . . .
N1 N 0.5771(5) 0.3997(2) 0.1809(5) 0.0327(10) Uani 1 1 d . . . . .
N2 N 0.4962(5) 0.4067(2) -0.0944(5) 0.0322(10) Uani 1 1 d . . . . .
N4 N 0.7083(8) 0.1026(3) 0.8761(6) 0.0542(16) Uani 1 1 d . . . . .
O1 O 0.2696(5) 0.31594(19) -0.1099(4) 0.0406(10) Uani 1 1 d . . . . .
O2 O 0.1086(5) 0.2447(2) -0.1496(5) 0.0523(12) Uani 1 1 d . . . . .
O3 O 0.3583(9) 0.1770(4) 0.7174(6) 0.126(4) Uani 1 1 d . . . . .
H3C H 0.4211 0.1515 0.7367 0.189 Uiso 1 1 calc R U . . .
O5 O 0.6445(8) 0.1098(3) 0.7537(6) 0.096(2) Uani 1 1 d . . . . .
O6 O 0.8304(8) 0.1231(4) 0.9154(9) 0.118(3) Uani 1 1 d . . . . .
O7 O 0.6612(10) 0.0766(4) 0.9574(9) 0.139(4) Uani 1 1 d . . . . .
Pd1 Pd 0.42237(5) 0.35553(2) 0.03779(4) 0.03096(14) Uani 1 1 d . . . . .
N3 N 0.3475(5) 0.3010(2) 0.1632(5) 0.0339(11) Uani 1 1 d . . . . .
H3A H 0.4178 0.2777 0.2162 0.05(2) Uiso 1 1 d D . . . .
H3B H 0.3208 0.3215 0.2229 0.05(2) Uiso 1 1 d D . . . .
O4 O 0.5321(10) 0.1330(5) 0.1448(9) 0.129(3) Uani 1 1 d D . . . .
H4A H 0.568(6) 0.1662(13) 0.169(12) 0.193 Uiso 1 1 d D U . . .
H4B H 0.570(15) 0.124(6) 0.082(12) 0.193 Uiso 1 1 d D U . . .
C14A C 0.2234(16) 0.2670(6) 0.0805(10) 0.071(5) Uani 0.75(2) 1 d . . P B 1
H14A H 0.1489 0.2951 0.0883 0.085 Uiso 0.75(2) 1 calc DR U P B 1
C14B C 0.304(3) 0.2410(14) 0.077(3) 0.071(5) Uani 0.25(2) 1 d . . P B 2
H14B H 0.3799 0.2133 0.0713 0.085 Uiso 0.25(2) 1 calc DR U P B 2


_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
C1 N1 1.320(7) . ?
C1 C2 1.394(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(9) . ?
C3 H3 0.9300 . ?
C4 C12 1.408(8) . ?
C4 C5 1.429(10) . ?
C5 C6 1.342(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.429(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.404(10) . ?
C7 C11 1.409(8) . ?
C8 C9 1.359(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.399(9) . ?
C9 H9 0.9300 . ?
C10 N2 1.326(7) . ?
C10 H10 0.9300 . ?
C11 N2 1.362(7) . ?
C11 C12 1.420(8) . ?
C12 N1 1.368(7) . ?
C13 O2 1.215(7) . ?
C13 O1 1.290(7) . ?
C13 C14A 1.468(11) . ?
C13 C14B 1.70(4) . ?
C15 C14A 1.439(10) . ?
C15 C16 1.506(9) . ?
C15 C14B 1.683(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.362(10) . ?
C16 C17 1.377(10) . ?
C17 C18 1.392(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.334(13) . ?
C19 O3 1.373(9) . ?
C20 C21 1.384(10) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 Pd1 2.024(5) . ?
N2 Pd1 2.034(5) . ?
N4 O7 1.194(8) . ?
N4 O5 1.221(8) . ?
N4 O6 1.224(9) . ?
O1 Pd1 1.989(4) . ?
O3 H3C 0.8200 . ?
Pd1 N3 2.036(5) . ?
N3 C14A 1.469(9) . ?
N3 C14B 1.60(2) . ?
N3 H3A 0.91 . ?
N3 H3B 0.85 . ?
O4 H4A 0.84(2) . ?
O4 H4B 0.84(2) . ?
C14A H14A 0.9800 . ?
C14B H14B 0.9800 . ?

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 C1 C2 121.8(6) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 120.1(6) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C12 116.3(6) . . ?
C3 C4 C5 125.8(6) . . ?
C12 C4 C5 117.8(6) . . ?
C6 C5 C4 122.2(7) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 121.4(6) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C11 116.7(6) . . ?
C8 C7 C6 125.7(6) . . ?
C11 C7 C6 117.6(6) . . ?
C9 C8 C7 120.3(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.0(6) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
N2 C10 C9 121.2(6) . . ?
N2 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
N2 C11 C7 122.2(5) . . ?
N2 C11 C12 116.8(5) . . ?
C7 C11 C12 121.0(6) . . ?
N1 C12 C4 123.0(6) . . ?
N1 C12 C11 117.1(5) . . ?
C4 C12 C11 119.9(6) . . ?
O2 C13 O1 122.8(6) . . ?
O2 C13 C14A 119.5(6) . . ?
O1 C13 C14A 117.2(6) . . ?
O2 C13 C14B 118.5(8) . . ?
O1 C13 C14B 111.7(8) . . ?
C14A C15 C16 119.3(7) . . ?
C16 C15 C14B 111.3(13) . . ?
C14A C15 H15A 107.5 . . ?
C16 C15 H15A 107.5 . . ?
C14A C15 H15B 107.5 . . ?
C16 C15 H15B 107.5 . . ?
H15A C15 H15B 107.0 . . ?
C21 C16 C17 116.9(7) . . ?
C21 C16 C15 120.7(7) . . ?
C17 C16 C15 122.4(7) . . ?
C16 C17 C18 121.5(8) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 119.0(8) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C20 C19 O3 123.2(11) . . ?
C20 C19 C18 120.3(8) . . ?
O3 C19 C18 116.5(11) . . ?
C19 C20 C21 120.0(8) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 122.2(7) . . ?
C16 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C1 N1 C12 118.9(5) . . ?
C1 N1 Pd1 129.0(4) . . ?
C12 N1 Pd1 112.1(4) . . ?
C10 N2 C11 119.6(5) . . ?
C10 N2 Pd1 128.2(4) . . ?
C11 N2 Pd1 112.2(4) . . ?
O7 N4 O5 124.9(9) . . ?
O7 N4 O6 118.8(8) . . ?
O5 N4 O6 116.3(7) . . ?
C13 O1 Pd1 116.0(4) . . ?
C19 O3 H3C 109.5 . . ?
O1 Pd1 N1 176.79(18) . . ?
O1 Pd1 N2 95.32(18) . . ?
N1 Pd1 N2 81.80(19) . . ?
O1 Pd1 N3 82.50(18) . . ?
N1 Pd1 N3 100.42(19) . . ?
N2 Pd1 N3 177.15(19) . . ?
C14A N3 Pd1 110.0(5) . . ?
C14B N3 Pd1 105.6(10) . . ?
C14A N3 H3A 112.6(7) . . ?
C14B N3 H3A 82.1(15) . . ?
Pd1 N3 H3A 112.0 . . ?
C14A N3 H3B 109.1(8) . . ?
C14B N3 H3B 139.2(9) . . ?
Pd1 N3 H3B 109.0 . . ?
H3A N3 H3B 103.0 . . ?
H4A O4 H4B 102(3) . . ?
C15 C14A C13 122.2(7) . . ?
C15 C14A N3 121.2(7) . . ?
C13 C14A N3 112.9(7) . . ?
C15 C14A H14A 96.4 . . ?
C13 C14A H14A 96.4 . . ?
N3 C14A H14A 96.4 . . ?
N3 C14B C15 100.9(12) . . ?
N3 C14B C13 96(2) . . ?
C15 C14B C13 97.4(17) . . ?
N3 C14B H14B 119.4 . . ?
C15 C14B H14B 119.4 . . ?
C13 C14B H14B 119.4 . . ?

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
N1 C1 C2 C3 -1.2(10) . . . . ?
C1 C2 C3 C4 0.7(11) . . . . ?
C2 C3 C4 C12 0.0(10) . . . . ?
C2 C3 C4 C5 -179.1(7) . . . . ?
C3 C4 C5 C6 179.5(7) . . . . ?
C12 C4 C5 C6 0.5(11) . . . . ?
C4 C5 C6 C7 -1.5(12) . . . . ?
C5 C6 C7 C8 -177.6(7) . . . . ?
C5 C6 C7 C11 1.3(11) . . . . ?
C11 C7 C8 C9 -0.2(10) . . . . ?
C6 C7 C8 C9 178.7(7) . . . . ?
C7 C8 C9 C10 0.4(11) . . . . ?
C8 C9 C10 N2 0.0(10) . . . . ?
C8 C7 C11 N2 -0.3(9) . . . . ?
C6 C7 C11 N2 -179.3(6) . . . . ?
C8 C7 C11 C12 178.8(6) . . . . ?
C6 C7 C11 C12 -0.2(9) . . . . ?
C3 C4 C12 N1 -0.3(9) . . . . ?
C5 C4 C12 N1 178.8(6) . . . . ?
C3 C4 C12 C11 -178.5(6) . . . . ?
C5 C4 C12 C11 0.7(9) . . . . ?
N2 C11 C12 N1 0.1(8) . . . . ?
C7 C11 C12 N1 -179.1(5) . . . . ?
N2 C11 C12 C4 178.4(5) . . . . ?
C7 C11 C12 C4 -0.8(9) . . . . ?
C14A C15 C16 C21 -100.8(12) . . . . ?
C14B C15 C16 C21 -62.3(14) . . . . ?
C14A C15 C16 C17 79.9(13) . . . . ?
C14B C15 C16 C17 118.4(14) . . . . ?
C21 C16 C17 C18 1.2(10) . . . . ?
C15 C16 C17 C18 -179.5(7) . . . . ?
C16 C17 C18 C19 -2.4(12) . . . . ?
C17 C18 C19 C20 2.3(12) . . . . ?
C17 C18 C19 O3 179.8(7) . . . . ?
O3 C19 C20 C21 -178.4(7) . . . . ?
C18 C19 C20 C21 -1.0(12) . . . . ?
C17 C16 C21 C20 0.1(10) . . . . ?
C15 C16 C21 C20 -179.2(6) . . . . ?
C19 C20 C21 C16 -0.2(11) . . . . ?
C2 C1 N1 C12 0.9(9) . . . . ?
C2 C1 N1 Pd1 177.9(5) . . . . ?
C4 C12 N1 C1 -0.1(8) . . . . ?
C11 C12 N1 C1 178.1(5) . . . . ?
C4 C12 N1 Pd1 -177.6(5) . . . . ?
C11 C12 N1 Pd1 0.6(6) . . . . ?
C9 C10 N2 C11 -0.6(9) . . . . ?
C9 C10 N2 Pd1 -177.9(5) . . . . ?
C7 C11 N2 C10 0.8(8) . . . . ?
C12 C11 N2 C10 -178.4(5) . . . . ?
C7 C11 N2 Pd1 178.4(4) . . . . ?
C12 C11 N2 Pd1 -0.8(6) . . . . ?
O2 C13 O1 Pd1 -177.5(5) . . . . ?
C14A C13 O1 Pd1 11.0(11) . . . . ?
C14B C13 O1 Pd1 -27.3(10) . . . . ?
C16 C15 C14A C13 168.3(11) . . . . ?
C14B C15 C14A C13 82(3) . . . . ?
C16 C15 C14A N3 12(2) . . . . ?
C14B C15 C14A N3 -74.4(17) . . . . ?
O2 C13 C14A C15 16.2(19) . . . . ?
O1 C13 C14A C15 -171.9(11) . . . . ?
C14B C13 C14A C15 -82.4(18) . . . . ?
O2 C13 C14A N3 174.6(9) . . . . ?
O1 C13 C14A N3 -13.5(16) . . . . ?
C14B C13 C14A N3 76.0(17) . . . . ?
C14B N3 C14A C15 78(2) . . . . ?
Pd1 N3 C14A C15 167.9(12) . . . . ?
C14B N3 C14A C13 -80(3) . . . . ?
Pd1 N3 C14A C13 9.2(15) . . . . ?
C14A N3 C14B C15 -46.8(10) . . . . ?
Pd1 N3 C14B C15 -149.5(14) . . . . ?
C14A N3 C14B C13 52(2) . . . . ?
Pd1 N3 C14B C13 -50.8(11) . . . . ?
C14A C15 C14B N3 50.3(12) . . . . ?
C16 C15 C14B N3 -61(2) . . . . ?
C14A C15 C14B C13 -46.8(18) . . . . ?
C16 C15 C14B C13 -157.8(8) . . . . ?
O2 C13 C14B N3 -157.0(7) . . . . ?
O1 C13 C14B N3 51.4(12) . . . . ?
C14A C13 C14B N3 -55.5(12) . . . . ?
O2 C13 C14B C15 -55.2(14) . . . . ?
O1 C13 C14B C15 153.2(8) . . . . ?
C14A C13 C14B C15 46.3(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O2 0.93 2.57 3.165(8) 122.3 4_666
C1 H1 O6 0.93 2.52 3.203(11) 130.0 4_565
C9 H9 O6 0.93 2.51 3.238(10) 135.1 4_564
O3 H3C O5 0.82 2.31 3.084(12) 156.3 .
N3 H3A O2 0.91 2.02 2.881(6) 158.9(3) 4_666
N3 H3B O5 0.85 2.39 3.122(9) 144.3(3) 4_565
N3 H3B O6 0.85 2.28 3.104(9) 160.9(4) 4_565
O4 H4B O7 0.84(2) 2.02(5) 2.834(13) 162(14) 1_554

_refine_diff_density_max         1.181
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.110

_shelxl_version_number           2013-4

