# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1965101'
loop_
_audit_author_name
_audit_author_address
'Prof. Jonathan M. White'
;The University of Melbourne
Australia
;
_audit_update_record             
;
2019-11-12 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 Cl N3 O Pd'
_chemical_formula_weight         436.22
_chemical_oxdiff_usercomment     'Tyra Horngren Pd complex'

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.5074(4)
_cell_length_b                   11.2005(6)
_cell_length_c                   11.2581(5)
_cell_angle_alpha                70.420(4)
_cell_angle_beta                 78.131(4)
_cell_angle_gamma                84.462(4)
_cell_volume                     872.46(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    7049
_cell_measurement_theta_min      2.7640
_cell_measurement_theta_max      35.3450

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    1.226
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.725
_oxdiff_exptl_absorpt_empirical_full_max 2.086
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      99.95(15)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19203
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0455
_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       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.774
_diffrn_reflns_theta_max         37.213
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8018
_reflns_number_gt                6236
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0503P)²] 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         8018
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.8244(4) 0.4777(2) 0.4072(3) 0.0250(5) Uani 1 1 d . . . . .
H1 H 0.773237 0.398586 0.448714 0.030 Uiso 1 1 calc R U . . .
C2 C 0.9285(4) 0.5007(2) 0.2841(3) 0.0286(5) Uani 1 1 d . . . . .
H2 H 0.946588 0.437832 0.245540 0.034 Uiso 1 1 calc R U . . .
C3 C 1.0031(4) 0.6159(2) 0.2213(3) 0.0263(5) Uani 1 1 d . . . . .
H3 H 1.072410 0.632227 0.139262 0.032 Uiso 1 1 calc R U . . .
C4 C 0.9752(3) 0.7120(2) 0.2810(2) 0.0233(5) Uani 1 1 d . . . . .
C5 C 1.0449(3) 0.8344(2) 0.2251(2) 0.0238(5) Uani 1 1 d . . . . .
C6 C 1.0179(4) 0.9199(2) 0.2918(3) 0.0254(5) Uani 1 1 d . . . . .
H6 H 1.067504 0.999830 0.253737 0.031 Uiso 1 1 calc R U . . .
C7 C 0.9156(4) 0.8867(2) 0.4172(2) 0.0245(5) Uani 1 1 d . . . . .
H7 H 0.899755 0.945210 0.461018 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8379(3) 0.7693(2) 0.4771(2) 0.0208(4) Uani 1 1 d . . . . .
C9 C 0.8705(3) 0.6800(2) 0.4070(2) 0.0204(4) Uani 1 1 d . . . . .
C10 C 0.6708(4) 0.7984(2) 0.6768(2) 0.0229(5) Uani 1 1 d . . . . .
C11 C 0.5349(4) 0.7302(2) 0.7968(2) 0.0236(5) Uani 1 1 d . . . . .
C12 C 0.5253(4) 0.5880(2) 0.8140(3) 0.0286(5) Uani 1 1 d . . . . .
H12A H 0.398999 0.563714 0.837259 0.034 Uiso 1 1 calc R U . . .
H12B H 0.587245 0.537785 0.882941 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3466(4) 0.7980(2) 0.7799(3) 0.0259(5) Uani 1 1 d . . . . .
H13A H 0.255679 0.754304 0.852525 0.031 Uiso 1 1 calc R U . . .
H13B H 0.351557 0.883816 0.781040 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2860(4) 0.8037(3) 0.6571(3) 0.0308(6) Uani 1 1 d . . . . .
H14A H 0.359657 0.862036 0.584910 0.046 Uiso 1 1 calc R U . . .
H14B H 0.160649 0.831684 0.660970 0.046 Uiso 1 1 calc R U . . .
H14C H 0.299610 0.720965 0.647863 0.046 Uiso 1 1 calc R U . . .
C15 C 0.5890(4) 0.7497(3) 0.9140(2) 0.0275(5) Uani 1 1 d . . . . .
H15A H 0.578929 0.839525 0.903598 0.033 Uiso 1 1 calc R U . . .
H15B H 0.502716 0.706872 0.990191 0.033 Uiso 1 1 calc R U . . .
C16 C 0.7816(4) 0.7014(3) 0.9358(3) 0.0381(7) Uani 1 1 d . . . . .
H16A H 0.793101 0.612323 0.947311 0.057 Uiso 1 1 calc R U . . .
H16B H 0.803428 0.715776 1.010911 0.057 Uiso 1 1 calc R U . . .
H16C H 0.868907 0.745957 0.862672 0.057 Uiso 1 1 calc R U . . .
C17 C 0.5181(4) 0.2706(2) 0.7304(3) 0.0246(5) Uani 1 1 d . . . . .
C18 C 0.4708(4) 0.1388(2) 0.7605(3) 0.0330(6) Uani 1 1 d . . . . .
H18A H 0.361794 0.136433 0.729365 0.049 Uiso 1 1 calc R U . . .
H18B H 0.451116 0.097927 0.851671 0.049 Uiso 1 1 calc R U . . .
H18C H 0.568536 0.095567 0.720062 0.049 Uiso 1 1 calc R U . . .
N1 N 0.7947(3) 0.56301(19) 0.4681(2) 0.0229(4) Uani 1 1 d . . . . .
N2 N 0.7277(3) 0.72605(18) 0.5977(2) 0.0217(4) Uani 1 1 d . . . . .
N3 N 0.5549(3) 0.37356(19) 0.7070(2) 0.0239(4) Uani 1 1 d . . . . .
O1 O 0.7166(3) 0.90774(17) 0.65443(18) 0.0291(4) Uani 1 1 d . . . . .
Pd1 Pd 0.64184(3) 0.55255(2) 0.65109(2) 0.02072(6) Uani 1 1 d . . . . .
Cl1 Cl 1.16943(10) 0.87882(6) 0.06879(6) 0.03078(14) Uani 1 1 d . . . . .


_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(3) . ?
C1 C2 1.398(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.357(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.428(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(4) . ?
C4 C9 1.419(4) . ?
C5 C6 1.381(3) . ?
C5 Cl1 1.745(3) . ?
C6 C7 1.406(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(3) . ?
C7 H7 0.9300 . ?
C8 N2 1.391(3) . ?
C8 C9 1.445(3) . ?
C9 N1 1.376(3) . ?
C10 O1 1.233(3) . ?
C10 N2 1.377(3) . ?
C10 C11 1.530(4) . ?
C11 C15 1.545(3) . ?
C11 C12 1.546(3) . ?
C11 C13 1.555(4) . ?
C12 Pd1 2.012(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.522(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.532(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N3 1.141(3) . ?
C17 C18 1.462(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 Pd1 2.113(2) . ?
N2 Pd1 1.963(2) . ?
N3 Pd1 2.020(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
N1 C1 C2 123.4(2) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C9 118.0(2) . . ?
C5 C4 C3 125.0(2) . . ?
C9 C4 C3 117.0(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 Cl1 119.3(2) . . ?
C4 C5 Cl1 119.42(19) . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 121.8(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 N2 127.9(2) . . ?
C7 C8 C9 117.2(2) . . ?
N2 C8 C9 114.9(2) . . ?
N1 C9 C4 121.8(2) . . ?
N1 C9 C8 116.8(2) . . ?
C4 C9 C8 121.4(2) . . ?
O1 C10 N2 125.3(2) . . ?
O1 C10 C11 122.2(2) . . ?
N2 C10 C11 112.5(2) . . ?
C10 C11 C15 108.4(2) . . ?
C10 C11 C12 111.9(2) . . ?
C15 C11 C12 111.6(2) . . ?
C10 C11 C13 106.48(19) . . ?
C15 C11 C13 107.9(2) . . ?
C12 C11 C13 110.3(2) . . ?
C11 C12 Pd1 110.67(18) . . ?
C11 C12 H12A 109.5 . . ?
Pd1 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
Pd1 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C11 114.4(2) . . ?
C14 C13 H13A 108.7 . . ?
C11 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C11 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C11 114.8(2) . . ?
C16 C15 H15A 108.6 . . ?
C11 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C11 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 179.9(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C9 118.4(2) . . ?
C1 N1 Pd1 130.61(19) . . ?
C9 N1 Pd1 110.98(15) . . ?
C10 N2 C8 124.3(2) . . ?
C10 N2 Pd1 119.30(17) . . ?
C8 N2 Pd1 116.36(15) . . ?
C17 N3 Pd1 173.9(2) . . ?
N2 Pd1 C12 83.74(10) . . ?
N2 Pd1 N3 179.56(8) . . ?
C12 Pd1 N3 96.12(10) . . ?
N2 Pd1 N1 81.00(8) . . ?
C12 Pd1 N1 164.65(10) . . ?
N3 Pd1 N1 99.13(8) . . ?

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 -0.6(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -179.7(2) . . . . ?
C2 C3 C4 C9 1.0(3) . . . . ?
C9 C4 C5 C6 2.1(3) . . . . ?
C3 C4 C5 C6 -177.2(2) . . . . ?
C9 C4 C5 Cl1 -178.37(17) . . . . ?
C3 C4 C5 Cl1 2.4(3) . . . . ?
C4 C5 C6 C7 -1.4(4) . . . . ?
Cl1 C5 C6 C7 179.02(19) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 N2 -177.0(2) . . . . ?
C6 C7 C8 C9 1.8(4) . . . . ?
C5 C4 C9 N1 179.0(2) . . . . ?
C3 C4 C9 N1 -1.7(3) . . . . ?
C5 C4 C9 C8 -0.8(3) . . . . ?
C3 C4 C9 C8 178.5(2) . . . . ?
C7 C8 C9 N1 179.1(2) . . . . ?
N2 C8 C9 N1 -1.9(3) . . . . ?
C7 C8 C9 C4 -1.1(3) . . . . ?
N2 C8 C9 C4 177.9(2) . . . . ?
O1 C10 C11 C15 -46.9(3) . . . . ?
N2 C10 C11 C15 135.4(2) . . . . ?
O1 C10 C11 C12 -170.4(2) . . . . ?
N2 C10 C11 C12 11.9(3) . . . . ?
O1 C10 C11 C13 69.0(3) . . . . ?
N2 C10 C11 C13 -108.7(2) . . . . ?
C10 C11 C12 Pd1 -15.1(3) . . . . ?
C15 C11 C12 Pd1 -136.78(19) . . . . ?
C13 C11 C12 Pd1 103.3(2) . . . . ?
C10 C11 C13 C14 55.5(3) . . . . ?
C15 C11 C13 C14 171.8(2) . . . . ?
C12 C11 C13 C14 -66.1(3) . . . . ?
C10 C11 C15 C16 -58.6(3) . . . . ?
C12 C11 C15 C16 65.1(3) . . . . ?
C13 C11 C15 C16 -173.5(2) . . . . ?
C2 C1 N1 C9 -0.1(4) . . . . ?
C2 C1 N1 Pd1 179.16(18) . . . . ?
C4 C9 N1 C1 1.3(3) . . . . ?
C8 C9 N1 C1 -178.9(2) . . . . ?
C4 C9 N1 Pd1 -178.10(17) . . . . ?
C8 C9 N1 Pd1 1.7(2) . . . . ?
O1 C10 N2 C8 -3.7(4) . . . . ?
C11 C10 N2 C8 173.9(2) . . . . ?
O1 C10 N2 Pd1 179.3(2) . . . . ?
C11 C10 N2 Pd1 -3.1(3) . . . . ?
C7 C8 N2 C10 2.9(4) . . . . ?
C9 C8 N2 C10 -175.9(2) . . . . ?
C7 C8 N2 Pd1 180.0(2) . . . . ?
C9 C8 N2 Pd1 1.2(3) . . . . ?

_refine_diff_density_max         1.720
_refine_diff_density_min         -2.367
_refine_diff_density_rms         0.145


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform, hexane'
_exptl_crystal_preparation       Luminescent
