# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_aff_a
_database_code_depnum_ccdc_archive 'CCDC 2195475'
loop_
_audit_author_name
_audit_author_address
'Jinyuan Wang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-08-09 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 Cl4 N2 O Pd'
_chemical_formula_weight         450.45

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      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                   11.2463(4)
_cell_length_b                   16.6685(5)
_cell_length_c                   8.6060(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.3450(10)
_cell_angle_gamma                90
_cell_volume                     1603.39(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9198
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.819
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_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_reflns_number            15001
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.194
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3687
_reflns_number_gt                3353
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+0.4418P] 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         3687
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_restrained_S_all      0.810
_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
Pd1 Pd 0.44181(2) 0.16935(2) 0.31019(2) 0.02357(10) Uani 1 1 d . . . . .
Cl1 Cl 0.52443(6) 0.05301(3) 0.21858(8) 0.03603(16) Uani 1 1 d . . . . .
Cl4 Cl 0.81501(10) 0.31729(5) 0.47563(10) 0.0552(2) Uani 1 1 d . . . . .
Cl2 Cl 0.90514(10) 0.39018(6) 0.76820(10) 0.0658(3) Uani 1 1 d . . . . .
Cl3 Cl 0.82147(16) 0.48776(6) 0.50016(15) 0.1021(6) Uani 1 1 d . . . . .
O006 O 0.56634(16) 0.25026(11) 0.2141(2) 0.0307(4) Uani 1 1 d . . . . .
N1 N 0.37890(18) 0.27202(11) 0.3831(2) 0.0244(4) Uani 1 1 d . . . . .
N2 N 0.5996(2) 0.38264(12) 0.1872(3) 0.0326(4) Uani 1 1 d . . . . .
H2 H 0.578441 0.430472 0.209565 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5421(2) 0.32191(14) 0.2418(3) 0.0265(5) Uani 1 1 d . . . . .
C8 C 0.2897(2) 0.28364(14) 0.4597(3) 0.0283(5) Uani 1 1 d . . . . .
H8 H 0.270996 0.336632 0.480455 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3205(3) 0.10243(15) 0.4014(3) 0.0355(6) Uani 1 1 d . . . . .
H7A H 0.276779 0.073224 0.315822 0.043 Uiso 1 1 calc R U . . .
H7B H 0.363775 0.062900 0.468302 0.043 Uiso 1 1 calc R U . . .
C1 C 0.2297(2) 0.13962(16) 0.4938(3) 0.0307(5) Uani 1 1 d . . . . .
C2 C 0.2148(2) 0.22235(15) 0.5175(3) 0.0284(5) Uani 1 1 d . . . . .
C10 C 0.4454(2) 0.34345(16) 0.3422(3) 0.0320(5) Uani 1 1 d . . . . .
H10A H 0.481011 0.369292 0.437083 0.038 Uiso 1 1 calc R U . . .
H10B H 0.390521 0.381208 0.286495 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1531(3) 0.08743(18) 0.5626(4) 0.0405(6) Uani 1 1 d . . . . .
H3 H 0.161571 0.032426 0.549393 0.049 Uiso 1 1 calc R U . . .
C4 C 0.1239(3) 0.24942(17) 0.6053(3) 0.0368(6) Uani 1 1 d . . . . .
H4 H 0.113949 0.304219 0.619509 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0499(3) 0.1965(2) 0.6702(3) 0.0403(7) Uani 1 1 d . . . . .
H5 H -0.009946 0.215290 0.727299 0.048 Uiso 1 1 calc R U . . .
C6 C 0.0653(3) 0.1152(2) 0.6497(4) 0.0443(7) Uani 1 1 d . . . . .
H6 H 0.016455 0.078873 0.694597 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6968(3) 0.37306(17) 0.0912(3) 0.0398(6) Uani 1 1 d . . . . .
H11A H 0.769250 0.393930 0.145862 0.060 Uiso 1 1 calc R U . . .
H11B H 0.678395 0.401750 -0.005204 0.060 Uiso 1 1 calc R U . . .
H11C H 0.707103 0.317169 0.069334 0.060 Uiso 1 1 calc R U . . .
C12 C 0.8018(3) 0.3993(2) 0.5998(4) 0.0494(7) Uani 1 1 d . . . . .
H12 H 0.720874 0.399198 0.632066 0.059 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 N1 1.9803(19) . ?
Pd1 C7 1.990(3) . ?
Pd1 O006 2.1725(18) . ?
Pd1 Cl1 2.3255(6) . ?
Cl4 C12 1.752(3) . ?
Cl2 C12 1.762(3) . ?
Cl3 C12 1.732(4) . ?
O006 C9 1.254(3) . ?
N1 C8 1.274(3) . ?
N1 C10 1.469(3) . ?
N2 C9 1.315(3) . ?
N2 C11 1.450(4) . ?
N2 H2 0.8600 . ?
C9 C10 1.506(4) . ?
C8 C2 1.447(4) . ?
C8 H8 0.9300 . ?
C7 C1 1.496(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 C3 1.401(4) . ?
C1 C2 1.407(3) . ?
C2 C4 1.410(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 C6 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 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 Pd1 C7 94.28(9) . . ?
N1 Pd1 O006 81.50(7) . . ?
C7 Pd1 O006 175.70(9) . . ?
N1 Pd1 Cl1 176.66(6) . . ?
C7 Pd1 Cl1 89.05(8) . . ?
O006 Pd1 Cl1 95.17(5) . . ?
C9 O006 Pd1 110.88(16) . . ?
C8 N1 C10 116.8(2) . . ?
C8 N1 Pd1 128.65(17) . . ?
C10 N1 Pd1 114.52(16) . . ?
C9 N2 C11 123.4(2) . . ?
C9 N2 H2 118.3 . . ?
C11 N2 H2 118.3 . . ?
O006 C9 N2 122.7(2) . . ?
O006 C9 C10 121.5(2) . . ?
N2 C9 C10 115.9(2) . . ?
N1 C8 C2 126.3(2) . . ?
N1 C8 H8 116.8 . . ?
C2 C8 H8 116.8 . . ?
C1 C7 Pd1 121.02(18) . . ?
C1 C7 H7A 107.1 . . ?
Pd1 C7 H7A 107.1 . . ?
C1 C7 H7B 107.1 . . ?
Pd1 C7 H7B 107.1 . . ?
H7A C7 H7B 106.8 . . ?
C3 C1 C2 117.3(2) . . ?
C3 C1 C7 117.1(2) . . ?
C2 C1 C7 125.6(2) . . ?
C1 C2 C4 119.8(2) . . ?
C1 C2 C8 124.0(2) . . ?
C4 C2 C8 116.3(2) . . ?
N1 C10 C9 111.3(2) . . ?
N1 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C6 C3 C1 122.0(3) . . ?
C6 C3 H3 119.0 . . ?
C1 C3 H3 119.0 . . ?
C5 C4 C2 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C2 C4 H4 119.3 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C3 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C3 C6 H6 119.8 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Cl3 C12 Cl4 109.76(18) . . ?
Cl3 C12 Cl2 111.8(2) . . ?
Cl4 C12 Cl2 109.97(16) . . ?
Cl3 C12 H12 108.4 . . ?
Cl4 C12 H12 108.4 . . ?
Cl2 C12 H12 108.4 . . ?

_refine_diff_density_max         0.758
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.081

