# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_21aprc
_database_code_depnum_ccdc_archive 'CCDC 2516819'
loop_
_audit_author_name
_audit_author_address
'Prem Lama'
;CSIR Indian Institute of Petroleum
India
;
_audit_update_record             
;
2025-12-17 deposited with the CCDC.	2026-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Cl2 N4 O Pd'
_chemical_formula_weight         457.63

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'
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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0409(10)
_cell_length_b                   7.1271(8)
_cell_length_c                   27.278(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.896(3)
_cell_angle_gamma                90
_cell_volume                     1748.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.6524
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.377
_shelx_estimated_absorpt_T_min   0.716
_shelx_estimated_absorpt_T_max   0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22061
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.955
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3082
_reflns_number_gt                2956
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+10.6298P] 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         3082
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.441
_refine_ls_restrained_S_all      1.441
_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
Pd1 Pd 0.55136(5) 0.20791(6) 0.52617(2) 0.01327(13) Uani 1 1 d . . . . .
Cl1 Cl 0.71855(15) 0.1287(2) 0.59559(5) 0.0188(3) Uani 1 1 d . . . . .
Cl2 Cl 0.74357(15) 0.3025(2) 0.48309(5) 0.0192(3) Uani 1 1 d . . . . .
O1 O 0.4599(4) 0.3118(6) 0.34825(14) 0.0207(9) Uani 1 1 d . . . . .
N1 N 0.3659(5) 0.1379(6) 0.56087(17) 0.0127(10) Uani 1 1 d . . . . .
N2 N 0.2551(5) 0.2434(6) 0.48742(17) 0.0134(10) Uani 1 1 d . . . . .
N3 N 0.1425(5) 0.2845(7) 0.45332(17) 0.0192(11) Uani 1 1 d . . . . .
N4 N 0.2129(5) 0.3492(7) 0.41725(17) 0.0166(10) Uani 1 1 d . . . . .
C1 C 0.3639(7) 0.0636(8) 0.6059(2) 0.0179(12) Uani 1 1 d . . . . .
H1 H 0.455389 0.035851 0.624798 0.022 Uiso 1 1 calc R U . . .
C2 C 0.2316(6) 0.0263(8) 0.6255(2) 0.0202(13) Uani 1 1 d . . . . .
H2 H 0.232061 -0.027892 0.657343 0.024 Uiso 1 1 calc R U . . .
C3 C 0.0987(6) 0.0692(8) 0.5980(2) 0.0194(13) Uani 1 1 d . . . . .
H3 H 0.007038 0.046139 0.611080 0.023 Uiso 1 1 calc R U . . .
C4 C 0.0991(6) 0.1455(8) 0.5514(2) 0.0185(13) Uani 1 1 d . . . . .
H4 H 0.009312 0.177976 0.532044 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2353(6) 0.1723(7) 0.5343(2) 0.0124(11) Uani 1 1 d . . . . .
C6 C 0.3955(6) 0.2741(8) 0.4734(2) 0.0149(12) Uani 1 1 d . . . . .
C7 C 0.3648(6) 0.3452(8) 0.4266(2) 0.0149(12) Uani 1 1 d . . . . .
C8 C 0.1240(7) 0.4150(9) 0.3730(2) 0.0262(15) Uani 1 1 d . . . . .
H8A H 0.151583 0.345178 0.344332 0.039 Uiso 1 1 calc R U . . .
H8B H 0.142424 0.549090 0.368398 0.039 Uiso 1 1 calc R U . . .
H8C H 0.018357 0.395112 0.376436 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4660(6) 0.4234(8) 0.3924(2) 0.0171(12) Uani 1 1 d . . . . .
H9A H 0.436723 0.554146 0.383848 0.021 Uiso 1 1 calc R U . . .
H9B H 0.568977 0.425055 0.408738 0.021 Uiso 1 1 calc R U . . .
C10 C 0.5682(7) 0.3520(8) 0.3177(2) 0.0182(13) Uani 1 1 d . . . . .
C11 C 0.5648(7) 0.2460(9) 0.2746(2) 0.0247(14) Uani 1 1 d . . . . .
H11 H 0.488447 0.155749 0.267101 0.030 Uiso 1 1 calc R U . . .
C12 C 0.6724(7) 0.2723(9) 0.2428(2) 0.0269(14) Uani 1 1 d . . . . .
H12 H 0.669617 0.198774 0.213676 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7852(7) 0.4049(10) 0.2526(2) 0.0276(15) Uani 1 1 d . . . . .
C14 C 0.7848(7) 0.5105(9) 0.2951(2) 0.0246(14) Uani 1 1 d . . . . .
H14 H 0.859796 0.602747 0.302179 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6787(7) 0.4860(8) 0.3277(2) 0.0208(13) Uani 1 1 d . . . . .
H15 H 0.681406 0.560301 0.356663 0.025 Uiso 1 1 calc R U . . .
C16 C 0.9041(8) 0.4354(12) 0.2175(3) 0.0424(19) Uani 1 1 d . . . . .
H16A H 0.869531 0.529876 0.192838 0.064 Uiso 1 1 calc R U . . .
H16B H 0.922956 0.317058 0.200968 0.064 Uiso 1 1 calc R U . . .
H16C H 0.996050 0.478953 0.236197 0.064 Uiso 1 1 calc R U . . .


_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 C6 1.965(6) . ?
Pd1 N1 2.069(5) . ?
Pd1 Cl2 2.2968(14) . ?
Pd1 Cl1 2.3668(15) . ?
O1 C10 1.380(7) . ?
O1 C9 1.440(7) . ?
N1 C1 1.338(7) . ?
N1 C5 1.344(7) . ?
N2 N3 1.339(6) . ?
N2 C6 1.380(7) . ?
N2 C5 1.403(7) . ?
N3 N4 1.309(7) . ?
N4 C7 1.371(7) . ?
N4 C8 1.458(7) . ?
C1 C2 1.386(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(8) . ?
C4 H4 0.9500 . ?
C6 C7 1.377(8) . ?
C7 C9 1.480(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.389(8) . ?
C10 C11 1.395(8) . ?
C11 C12 1.381(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(9) . ?
C13 C16 1.527(9) . ?
C14 C15 1.384(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C6 Pd1 N1 80.7(2) . . ?
C6 Pd1 Cl2 94.48(16) . . ?
N1 Pd1 Cl2 174.89(13) . . ?
C6 Pd1 Cl1 173.76(16) . . ?
N1 Pd1 Cl1 93.28(13) . . ?
Cl2 Pd1 Cl1 91.43(5) . . ?
C10 O1 C9 115.0(4) . . ?
C1 N1 C5 118.2(5) . . ?
C1 N1 Pd1 127.1(4) . . ?
C5 N1 Pd1 114.7(4) . . ?
N3 N2 C6 115.4(5) . . ?
N3 N2 C5 123.5(4) . . ?
C6 N2 C5 121.1(5) . . ?
N4 N3 N2 101.9(4) . . ?
N3 N4 C7 114.1(5) . . ?
N3 N4 C8 117.8(5) . . ?
C7 N4 C8 128.0(5) . . ?
N1 C1 C2 121.6(5) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 118.9(6) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 117.0(5) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
N1 C5 C4 124.0(5) . . ?
N1 C5 N2 111.7(5) . . ?
C4 C5 N2 124.2(5) . . ?
C7 C6 N2 102.2(5) . . ?
C7 C6 Pd1 146.0(4) . . ?
N2 C6 Pd1 111.7(4) . . ?
N4 C7 C6 106.4(5) . . ?
N4 C7 C9 123.2(5) . . ?
C6 C7 C9 130.1(5) . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 C7 110.2(5) . . ?
O1 C9 H9A 109.6 . . ?
C7 C9 H9A 109.6 . . ?
O1 C9 H9B 109.6 . . ?
C7 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O1 C10 C15 124.3(5) . . ?
O1 C10 C11 116.2(5) . . ?
C15 C10 C11 119.4(6) . . ?
C12 C11 C10 119.9(6) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.3(6) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 117.7(6) . . ?
C14 C13 C16 120.7(6) . . ?
C12 C13 C16 121.6(6) . . ?
C13 C14 C15 122.1(6) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C10 119.5(6) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C6 N2 N3 N4 -2.2(6) . . . . ?
C5 N2 N3 N4 178.4(4) . . . . ?
N2 N3 N4 C7 1.9(6) . . . . ?
N2 N3 N4 C8 -178.2(5) . . . . ?
C5 N1 C1 C2 -1.4(8) . . . . ?
Pd1 N1 C1 C2 178.7(4) . . . . ?
N1 C1 C2 C3 -0.8(9) . . . . ?
C1 C2 C3 C4 0.9(9) . . . . ?
C2 C3 C4 C5 1.1(8) . . . . ?
C1 N1 C5 C4 3.7(8) . . . . ?
Pd1 N1 C5 C4 -176.4(4) . . . . ?
C1 N1 C5 N2 -177.8(4) . . . . ?
Pd1 N1 C5 N2 2.0(5) . . . . ?
C3 C4 C5 N1 -3.5(8) . . . . ?
C3 C4 C5 N2 178.2(5) . . . . ?
N3 N2 C5 N1 178.2(4) . . . . ?
C6 N2 C5 N1 -1.2(7) . . . . ?
N3 N2 C5 C4 -3.4(8) . . . . ?
C6 N2 C5 C4 177.3(5) . . . . ?
N3 N2 C6 C7 1.6(6) . . . . ?
C5 N2 C6 C7 -179.0(4) . . . . ?
N3 N2 C6 Pd1 -179.7(3) . . . . ?
C5 N2 C6 Pd1 -0.3(6) . . . . ?
N3 N4 C7 C6 -1.0(6) . . . . ?
C8 N4 C7 C6 179.1(5) . . . . ?
N3 N4 C7 C9 -175.6(5) . . . . ?
C8 N4 C7 C9 4.5(9) . . . . ?
N2 C6 C7 N4 -0.3(6) . . . . ?
Pd1 C6 C7 N4 -178.1(6) . . . . ?
N2 C6 C7 C9 173.8(5) . . . . ?
Pd1 C6 C7 C9 -4.0(12) . . . . ?
C10 O1 C9 C7 -169.2(5) . . . . ?
N4 C7 C9 O1 -68.8(7) . . . . ?
C6 C7 C9 O1 118.0(6) . . . . ?
C9 O1 C10 C15 1.2(8) . . . . ?
C9 O1 C10 C11 -179.9(5) . . . . ?
O1 C10 C11 C12 -177.6(5) . . . . ?
C15 C10 C11 C12 1.3(9) . . . . ?
C10 C11 C12 C13 -0.5(10) . . . . ?
C11 C12 C13 C14 -0.6(10) . . . . ?
C11 C12 C13 C16 -179.7(6) . . . . ?
C12 C13 C14 C15 0.9(10) . . . . ?
C16 C13 C14 C15 -179.9(6) . . . . ?
C13 C14 C15 C10 -0.2(9) . . . . ?
O1 C10 C15 C14 177.9(5) . . . . ?
C11 C10 C15 C14 -0.9(9) . . . . ?

_refine_diff_density_max         0.647
_refine_diff_density_min         -1.679
_refine_diff_density_rms         0.129

