# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2c6pd
_database_code_depnum_ccdc_archive 'CCDC 2109436'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2021-09-13 deposited with the CCDC.	2021-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H18 N2, Cl4 Pd'
_chemical_formula_sum            'C6 H18 Cl4 N2 Pd'
_chemical_formula_weight         366.42

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2281(7)
_cell_length_b                   8.1281(5)
_cell_length_c                   11.7212(12)
_cell_angle_alpha                70.892(4)
_cell_angle_beta                 87.545(5)
_cell_angle_gamma                89.101(3)
_cell_volume                     650.09(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      17.34

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    2.212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_T_max  0.795
_exptl_absorpt_process_details   scalepack

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'DIP 2000'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3421
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.45
_reflns_number_total             2982
_reflns_number_gt                2940
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Nonius Collect'
_computing_cell_refinement       'HKL Denzo'
_computing_data_reduction        'HKL Denzo'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Atoms
_computing_publication_material  PublCIF

_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)+(0.0759P)²+0.0000P] 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         2982
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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 0.0000 0.0000 0.0000 0.02349(10) Uani 1 2 d S . .
Cl1 Cl 0.22244(3) 0.21134(3) -0.02758(2) 0.03432(11) Uani 1 1 d . . .
Cl2 Cl -0.00831(5) -0.04359(4) 0.20549(2) 0.04025(11) Uani 1 1 d . . .
Pd2 Pd 0.5000 0.5000 0.0000 0.02392(10) Uani 1 2 d S . .
Cl3 Cl 0.28499(3) 0.68529(4) 0.04379(3) 0.03445(11) Uani 1 1 d . . .
Cl4 Cl 0.53156(4) 0.35817(5) 0.20441(2) 0.03884(11) Uani 1 1 d . . .
N1 N 0.50387(19) 0.0498(2) 0.81316(12) 0.0505(3) Uani 1 1 d . . .
H1A H 0.4565 0.0881 0.8712 0.061 Uiso 1 1 d R . .
H1B H 0.4329 -0.0350 0.8067 0.061 Uiso 1 1 d R . .
H1C H 0.6177 0.0092 0.8314 0.061 Uiso 1 1 d R . .
C2 C 0.5121(3) 0.1949(3) 0.6968(2) 0.0503(4) Uani 1 1 d . . .
H2A H 0.5897 0.2868 0.7044 0.060 Uiso 1 1 calc R . .
H2B H 0.3886 0.2422 0.6786 0.060 Uiso 1 1 calc R . .
C3 C 0.5888(2) 0.1368(2) 0.59303(13) 0.0505(3) Uani 1 1 d . . .
H3A H 0.6306 0.2389 0.5275 0.061 Uiso 1 1 calc R . .
H3B H 0.6960 0.0633 0.6202 0.061 Uiso 1 1 calc R . .
C4 C 0.4550(4) 0.0393(3) 0.5448(2) 0.0516(5) Uani 1 1 d . . .
H4A H 0.3571 0.1180 0.5056 0.062 Uiso 1 1 calc R . .
H4B H 0.3988 -0.0530 0.6117 0.062 Uiso 1 1 calc R . .
N5 N -0.01497(18) 0.3734(2) 0.16637(11) 0.0454(3) Uani 1 1 d U . .
H5A H 0.0248 0.2901 0.1375 0.054 Uiso 1 1 d R . .
H5B H -0.1373 0.3841 0.1609 0.054 Uiso 1 1 d R . .
H5C H 0.0387 0.4738 0.1237 0.054 Uiso 1 1 d R . .
C6 C 0.0330(3) 0.3282(3) 0.2950(2) 0.0498(4) Uani 1 1 d U . .
H6A H 0.1661 0.3148 0.3014 0.060 Uiso 1 1 calc R . .
H6B H -0.0241 0.2181 0.3416 0.060 Uiso 1 1 calc R . .
C7 C -0.0321(2) 0.4664(2) 0.34548(13) 0.0508(3) Uani 1 1 d U . .
H7A H -0.1663 0.4699 0.3480 0.061 Uiso 1 1 calc R . .
H7B H 0.0127 0.5787 0.2930 0.061 Uiso 1 1 calc R . .
C8 C 0.0367(4) 0.4329(4) 0.4728(2) 0.0513(4) Uani 1 1 d U . .
H8A H -0.0026 0.3180 0.5241 0.062 Uiso 1 1 calc R . .
H8B H 0.1710 0.4353 0.4695 0.062 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 0.02212(14) 0.02133(14) 0.03061(13) -0.01307(9) -0.00400(8) 0.00063(8)
Cl1 0.02646(17) 0.03222(17) 0.04966(18) -0.02076(14) 0.00103(12) -0.00629(12)
Cl2 0.0599(2) 0.03240(19) 0.03067(17) -0.01266(14) -0.00614(13) -0.00266(15)
Pd2 0.01918(13) 0.02199(14) 0.03222(13) -0.01089(9) -0.00286(8) 0.00124(8)
Cl3 0.02699(16) 0.03298(17) 0.04835(18) -0.02027(13) -0.00255(12) 0.00713(11)
Cl4 0.03748(17) 0.0418(2) 0.03394(17) -0.00791(14) -0.00276(12) 0.00352(13)
N1 0.0498(7) 0.0501(8) 0.0517(6) -0.0167(6) -0.0020(5) -0.0005(6)
C2 0.0508(10) 0.0488(9) 0.0511(8) -0.0162(7) -0.0015(7) -0.0008(7)
C3 0.0498(7) 0.0510(8) 0.0509(7) -0.0168(6) -0.0017(5) -0.0001(6)
C4 0.0510(9) 0.0514(11) 0.0524(10) -0.0170(8) -0.0022(7) -0.0010(8)
N5 0.0470(6) 0.0458(6) 0.0462(6) -0.0186(5) -0.0022(4) -0.0001(5)
C6 0.0506(8) 0.0504(8) 0.0487(7) -0.0164(6) -0.0021(6) -0.0002(6)
C7 0.0519(6) 0.0517(7) 0.0497(6) -0.0178(5) -0.0015(5) -0.0003(5)
C8 0.0516(8) 0.0518(8) 0.0511(8) -0.0177(7) -0.0018(6) -0.0002(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 Cl1 2.3063(3) . ?
Pd1 Cl1 2.3063(3) 2 ?
Pd1 Cl2 2.3152(4) . ?
Pd1 Cl2 2.3152(4) 2 ?
Pd2 Cl3 2.3046(3) 2_665 ?
Pd2 Cl3 2.3046(3) . ?
Pd2 Cl4 2.3134(3) 2_665 ?
Pd2 Cl4 2.3134(3) . ?
N1 C2 1.482(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8899 . ?
C2 C3 1.523(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.499(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C4 1.517(5) 2_656 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N5 C6 1.486(3) . ?
N5 H5A 0.8899 . ?
N5 H5B 0.8899 . ?
N5 H5C 0.8900 . ?
C6 C7 1.492(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.530(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C8 1.512(6) 2_566 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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
Cl1 Pd1 Cl1 180.0 . 2 ?
Cl1 Pd1 Cl2 89.311(11) . . ?
Cl1 Pd1 Cl2 90.690(11) 2 . ?
Cl1 Pd1 Cl2 90.690(11) . 2 ?
Cl1 Pd1 Cl2 89.310(11) 2 2 ?
Cl2 Pd1 Cl2 180.0 . 2 ?
Cl3 Pd2 Cl3 180.0 2_665 . ?
Cl3 Pd2 Cl4 89.940(12) 2_665 2_665 ?
Cl3 Pd2 Cl4 90.060(13) . 2_665 ?
Cl3 Pd2 Cl4 90.060(13) 2_665 . ?
Cl3 Pd2 Cl4 89.940(12) . . ?
Cl4 Pd2 Cl4 180.0 2_665 . ?
C2 N1 H1A 109.6 . . ?
C2 N1 H1B 109.6 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.2 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C2 C3 112.13(19) . . ?
N1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 115.04(16) . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 C4 113.0(3) . 2_656 ?
C3 C4 H4A 109.0 . . ?
C4 C4 H4A 109.0 2_656 . ?
C3 C4 H4B 109.0 . . ?
C4 C4 H4B 109.0 2_656 . ?
H4A C4 H4B 107.8 . . ?
C6 N5 H5A 109.8 . . ?
C6 N5 H5B 109.3 . . ?
H5A N5 H5B 109.5 . . ?
C6 N5 H5C 109.3 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
N5 C6 C7 110.76(19) . . ?
N5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 111.36(18) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C8 C7 111.8(3) 2_566 . ?
C8 C8 H8A 109.3 2_566 . ?
C7 C8 H8A 109.3 . . ?
C8 C8 H8B 109.3 2_566 . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?

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 C2 C3 C4 77.5(2) . . . . ?
C2 C3 C4 C4 -171.3(2) . . . 2_656 ?
N5 C6 C7 C8 -173.06(17) . . . . ?
C6 C7 C8 C8 -177.0(3) . . . 2_566 ?

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
N1 H1A Cl1 0.89 2.41 3.2467(16) 155.9 1_556
N1 H1B Cl4 0.89 2.68 3.4037(19) 139.1 2_656
N1 H1C Cl1 0.89 2.70 3.3968(14) 135.8 2_656
N5 H5A Cl1 0.89 2.60 3.3771(14) 147.0 .
N5 H5A Cl2 0.89 2.58 3.2683(17) 135.2 .
N5 H5B Cl4 0.89 2.42 3.2877(14) 163.7 1_455
N5 H5C Cl3 0.89 2.43 3.2728(14) 158.3 .
# N1 H1C Cl2  0.89 2.84 3.6439(14) 150.6 2_656
# N5 H5B Cl3  0.89 2.89 3.3640(14) 115.2 2_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.155
