# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_hadi0709
_database_code_depnum_ccdc_archive 'CCDC 2203863'
loop_
_audit_author_name
_audit_author_address
' Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2022-08-28 deposited with the CCDC.	2024-05-16 downloaded from the CCDC.
;

_audit_creation_date             2021-09-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 Br2 Cl N2 O Pd'
_chemical_formula_sum            'C14 H11 Br2 Cl N2 O Pd'
_chemical_formula_weight         524.92
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   15.0229(3)
_cell_length_b                   7.48770(10)
_cell_length_c                   15.3898(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.204(2)
_cell_angle_gamma                90
_cell_volume                     1566.34(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14390
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.2200
_cell_measurement_theta_min      3.1580
_shelx_estimated_absorpt_T_max   0.482
_shelx_estimated_absorpt_T_min   0.080
_exptl_absorpt_coefficient_mu    17.099
_exptl_absorpt_correction_T_max  0.523
_exptl_absorpt_correction_T_min  0.116
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0141
-1 0 -1 0.0331
-1 0 1 0.0642
1 0 -1 0.0642
-2 -5 2 0.1496
2 5 -2 0.1196
-3 4 -4 0.0985
-5 4 4 0.1203

_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05

_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16096
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.462
_diffrn_reflns_theta_min         3.443
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -20.00   1.00    1.00    --  -42.61 -37.00-150.00   96
  2  ω    -69.00  28.00   1.00    1.00    --  -42.61  57.00-180.00   97
  3  ω      6.00  83.00   1.00    1.00    --   42.61 -99.00  60.00   77
  4  ω     83.00 178.00   1.00    4.00    --  111.00  61.00-150.00   95
  5  ω    103.00 178.00   1.00    4.00    --  111.00  77.00 -90.00   75
  6  ω     36.00 109.00   1.00    4.00    --  111.00-111.00  60.00   73
  7  ω     36.00 109.00   1.00    4.00    --  111.00-111.00-150.00   73
  8  ω     36.00 135.00   1.00    4.00    --  111.00 -30.00 -30.00   99
  9  ω     30.00 107.00   1.00    4.00    --  111.00 -94.00 -30.00   77
 10  ω     36.00 109.00   1.00    4.00    --  111.00-111.00  30.00   73
 11  ω     40.00 135.00   1.00    4.00    --  111.00 -45.00-150.00   95
 12  ω    103.00 178.00   1.00    4.00    --  111.00  77.00-180.00   75
 13  ω     87.00 178.00   1.00    4.00    --  111.00  45.00 150.00   91
 14  ω     41.00 139.00   1.00    4.00    --  111.00 -61.00  60.00   98
 15  ω   -113.00 -16.00   1.00    1.00    --  -42.61 -57.00 -30.00   97
 16  ω   -116.00 -20.00   1.00    1.00    --  -42.61 -37.00  30.00   96
 17  ω   -116.00 -20.00   1.00    1.00    --  -42.61 -37.00 120.00   96
 18  ω     83.00 176.00   1.00    4.00    --  111.00  61.00 -30.00   93
 19  ω     87.00 178.00   1.00    4.00    --  111.00  45.00  90.00   91
 20  ω     87.00 178.00   1.00    4.00    --  111.00  30.00  30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0904846000
_diffrn_orient_matrix_UB_12      0.0621185000
_diffrn_orient_matrix_UB_13      0.0898942000
_diffrn_orient_matrix_UB_21      0.0666048000
_diffrn_orient_matrix_UB_22      -0.0407825000
_diffrn_orient_matrix_UB_23      -0.0508484000
_diffrn_orient_matrix_UB_31      -0.0149997000
_diffrn_orient_matrix_UB_32      0.1917303000
_diffrn_orient_matrix_UB_33      -0.0398349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3177
_reflns_number_total             3209

_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.00053(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0177
_refine_ls_R_factor_gt           0.0173
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0215P)²+1.4128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0434
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.51577(2) 0.27073(4) 0.63252(2) 0.03541(8) Uani 1 1 d . . . . .
Br2 Br 0.21132(2) 0.54766(4) 0.29313(2) 0.03769(8) Uani 1 1 d . . . . .
C1 C 0.32169(15) 0.3387(3) 0.61131(14) 0.0193(4) Uani 1 1 d . . . . .
C2 C 0.38368(15) 0.3440(3) 0.56266(15) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.35183(17) 0.4030(3) 0.46954(15) 0.0270(4) Uani 1 1 d . . . . .
H3 H 0.395328 0.405639 0.439327 0.032 Uiso 1 1 calc R U . . .
C4 C 0.25453(17) 0.4588(3) 0.42044(14) 0.0257(4) Uani 1 1 d . . . . .
C5 C 0.19099(15) 0.4551(3) 0.46305(14) 0.0237(4) Uani 1 1 d . . . . .
H5 H 0.124601 0.491727 0.427989 0.028 Uiso 1 1 calc R U . . .
C6 C 0.22399(14) 0.3971(3) 0.55890(14) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.15189(14) 0.3922(3) 0.59785(14) 0.0200(4) Uani 1 1 d . . . . .
H7 H 0.085488 0.411734 0.553512 0.024 Uiso 1 1 calc R U . . .
C8 C 0.07968(14) 0.3623(3) 0.70580(15) 0.0224(4) Uani 1 1 d . . . . .
H8A H 0.022085 0.319930 0.648319 0.027 Uiso 1 1 calc R U . . .
H8B H 0.065581 0.485231 0.720146 0.027 Uiso 1 1 calc R U . . .
C9 C 0.09521(15) 0.2414(3) 0.79049(15) 0.0239(4) Uani 1 1 d . . . . .
H9A H 0.030872 0.216798 0.791414 0.029 Uiso 1 1 calc R U . . .
H9B H 0.123016 0.126162 0.782278 0.029 Uiso 1 1 calc R U . . .
C10 C 0.16287(16) 0.3230(3) 0.88426(15) 0.0227(4) Uani 1 1 d . . . . .
C11 C 0.13392(18) 0.3484(3) 0.95782(17) 0.0295(5) Uani 1 1 d . . . . .
H11 H 0.070314 0.311329 0.949519 0.035 Uiso 1 1 calc R U . . .
C12 C 0.1970(2) 0.4273(3) 1.04300(17) 0.0337(5) Uani 1 1 d . . . . .
H12 H 0.177799 0.442796 1.093903 0.040 Uiso 1 1 calc R U . . .
C13 C 0.28857(19) 0.4833(3) 1.05293(16) 0.0311(5) Uani 1 1 d . . . . .
H13 H 0.333099 0.539141 1.110485 0.037 Uiso 1 1 calc R U . . .
C14 C 0.31415(16) 0.4565(3) 0.97767(15) 0.0247(4) Uani 1 1 d . . . . .
H14 H 0.376707 0.496348 0.984113 0.030 Uiso 1 1 calc R U . . .
Cl1 Cl 0.46054(3) 0.28608(7) 0.90721(3) 0.02666(11) Uani 1 1 d . . . . .
N1 N 0.16707(12) 0.3645(2) 0.68535(12) 0.0185(3) Uani 1 1 d . . . . .
N2 N 0.25313(13) 0.3755(2) 0.89509(12) 0.0207(3) Uani 1 1 d . . . . .
O1 O 0.35796(10) 0.2795(2) 0.69914(10) 0.0224(3) Uani 1 1 d . . . . .
Pd1 Pd 0.30132(2) 0.32862(2) 0.79211(2) 0.01675(6) 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
Br1 C2 1.892(2) . ?
Br2 C4 1.902(2) . ?
C1 C2 1.422(3) . ?
C1 C6 1.410(3) . ?
C1 O1 1.301(2) . ?
C2 C3 1.376(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 C5 1.369(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.410(3) . ?
C6 C7 1.445(3) . ?
C7 H7 0.9500 . ?
C7 N1 1.283(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.521(3) . ?
C8 N1 1.475(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.496(3) . ?
C10 C11 1.388(3) . ?
C10 N2 1.352(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(3) . ?
C14 H14 0.9500 . ?
C14 N2 1.353(3) . ?
Cl1 Pd1 2.3134(5) . ?
N1 Pd1 2.0044(16) . ?
N2 Pd1 2.0337(17) . ?
O1 Pd1 1.9857(14) . ?

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 C1 C2 116.46(18) . . ?
O1 C1 C2 118.56(19) . . ?
O1 C1 C6 124.97(19) . . ?
C1 C2 Br1 117.15(16) . . ?
C3 C2 Br1 120.03(16) . . ?
C3 C2 C1 122.8(2) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.7(2) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Br2 118.85(16) . . ?
C5 C4 Br2 119.90(17) . . ?
C5 C4 C3 121.23(19) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.06(19) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 122.45(18) . . ?
C5 C6 C1 120.71(19) . . ?
C5 C6 C7 116.76(18) . . ?
C6 C7 H7 116.2 . . ?
N1 C7 C6 127.59(18) . . ?
N1 C7 H7 116.2 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C9 111.34(16) . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.13(17) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C11 C10 C9 121.5(2) . . ?
N2 C10 C9 118.12(18) . . ?
N2 C10 C11 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 118.9 . . ?
N2 C14 C13 122.2(2) . . ?
N2 C14 H14 118.9 . . ?
C7 N1 C8 116.70(16) . . ?
C7 N1 Pd1 123.30(14) . . ?
C8 N1 Pd1 120.00(12) . . ?
C10 N2 C14 119.27(18) . . ?
C10 N2 Pd1 121.65(14) . . ?
C14 N2 Pd1 119.06(14) . . ?
C1 O1 Pd1 124.56(13) . . ?
N1 Pd1 Cl1 175.96(5) . . ?
N1 Pd1 N2 92.74(7) . . ?
N2 Pd1 Cl1 91.27(5) . . ?
O1 Pd1 Cl1 84.59(4) . . ?
O1 Pd1 N1 91.40(6) . . ?
O1 Pd1 N2 175.85(6) . . ?

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
Br1 C2 C3 C4 -178.99(16) . . . . ?
Br2 C4 C5 C6 -177.08(15) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C6 C7 N1 12.0(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 177.43(18) . . . . ?
C2 C1 O1 Pd1 160.15(14) . . . . ?
C2 C3 C4 Br2 178.00(16) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C5 C6 C7 -178.28(19) . . . . ?
C5 C6 C7 N1 -171.2(2) . . . . ?
C6 C1 C2 Br1 178.78(14) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C1 O1 Pd1 -20.6(3) . . . . ?
C6 C7 N1 C8 -178.6(2) . . . . ?
C6 C7 N1 Pd1 2.2(3) . . . . ?
C8 C9 C10 C11 123.3(2) . . . . ?
C8 C9 C10 N2 -55.3(2) . . . . ?
C9 C8 N1 C7 150.68(18) . . . . ?
C9 C8 N1 Pd1 -30.1(2) . . . . ?
C9 C10 C11 C12 -178.7(2) . . . . ?
C9 C10 N2 C14 177.22(18) . . . . ?
C9 C10 N2 Pd1 -4.8(2) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C10 N2 C14 -1.3(3) . . . . ?
C11 C10 N2 Pd1 176.61(15) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 N2 -0.8(3) . . . . ?
C13 C14 N2 C10 1.9(3) . . . . ?
C13 C14 N2 Pd1 -176.15(16) . . . . ?
N1 C8 C9 C10 74.1(2) . . . . ?
N2 C10 C11 C12 -0.2(3) . . . . ?
O1 C1 C2 Br1 -2.0(3) . . . . ?
O1 C1 C2 C3 179.47(19) . . . . ?
O1 C1 C6 C5 -178.51(19) . . . . ?
O1 C1 C6 C7 -1.8(3) . . . . ?

####################################################################### 
# 
# 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_hadi0202
_database_code_depnum_ccdc_archive 'CCDC 2203864'
loop_
_audit_author_name
_audit_author_address
' Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2022-08-28 deposited with the CCDC.	2024-05-16 downloaded from the CCDC.
;

_audit_creation_date             2022-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 Cl4 N2 O Pd, C2 H3 N'
_chemical_formula_sum            'C16 H17 Cl4 N3 O Pd'
_chemical_formula_weight         515.52
_chemical_melting_point          ?

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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6004(3)
_cell_length_b                   10.6416(5)
_cell_length_c                   12.0185(6)
_cell_angle_alpha                64.023(5)
_cell_angle_beta                 77.255(4)
_cell_angle_gamma                84.618(4)
_cell_volume                     964.46(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    21429
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      32.4950
_cell_measurement_theta_min      2.7720
_shelx_estimated_absorpt_T_max   0.862
_shelx_estimated_absorpt_T_min   0.692
_exptl_absorpt_coefficient_mu    1.526
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0563
0 0 1 0.0443
0 5 1 0.1208
0 -5 -4 0.0951
-5 0 -2 0.1186
5 0 1 0.1074
-1 5 2 0.1177
3 0 5 0.0864
2 5 5 0.1416

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10

_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35415
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         1.924
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 109.00   1.00    3.50    --   19.62   0.00-150.00  179
  2  ω    -27.00 101.00   1.00    3.50    --   19.62  19.00 -30.00  128
  3  ω     -7.00  96.00   1.00    3.50    --   19.62  37.00  30.00  103
  4  ω   -110.00 -61.00   1.00    3.50    --  -20.24-178.00 150.00   49
  5  ω    -42.00  13.00   1.00    3.50    --  -20.24 -77.00 -30.00   55
  6  ω   -110.00 -61.00   1.00    3.50    --  -20.24-178.00   0.00   49
  7  ω    -42.00  13.00   1.00    3.50    --  -20.24 -77.00 120.00   55
  8  ω    -15.00  62.00   1.00    3.50    --   19.62 -99.00 150.00   77
  9  ω    -15.00  62.00   1.00    3.50    --   19.62 -99.00 -60.00   77
 10  ω    -42.00  13.00   1.00    3.50    --  -20.24 -77.00  60.00   55
 11  ω    -42.00  13.00   1.00    3.50    --  -20.24 -77.00-150.00   55
 12  ω   -109.00 -58.00   1.00    3.50    --  -20.24 178.00  60.00   51
 13  ω   -110.00 -61.00   1.00    3.50    --  -20.24-178.00 -90.00   49
 14  ω    -15.00  62.00   1.00    3.50    --   19.62 -99.00  60.00   77
 15  ω    -15.00  62.00   1.00    3.50    --   19.62 -99.00-150.00   77
 16  ω    -42.00  13.00   1.00    3.50    --  -20.24 -77.00   0.00   55
 17  ω    -54.00  -2.00   1.00    3.50    --  -20.24  77.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0084967000
_diffrn_orient_matrix_UB_12      -0.0419602000
_diffrn_orient_matrix_UB_13      -0.0306930000
_diffrn_orient_matrix_UB_21      -0.0828612000
_diffrn_orient_matrix_UB_22      0.0144863000
_diffrn_orient_matrix_UB_23      0.0064660000
_diffrn_orient_matrix_UB_31      0.0145489000
_diffrn_orient_matrix_UB_32      0.0593879000
_diffrn_orient_matrix_UB_33      -0.0592173000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5361
_reflns_number_total             5887
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5887
_refine_ls_number_restraints     65
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0169P)²+0.6325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0494
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 N3A-C16B = N3B-C16A
 1.15 with sigma of 0.003
 C16B-C15 = C15-C16A
 1.45 with sigma of 0.003
 O1-H1A
 0.82 with sigma of 0.01
3. Restrained planarity
 C15, C16A, N3A, C16B, N3B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C15 \\sim C16A \\sim N3A \\sim C16B \\sim N3B: within 3A with sigma of 0.005
and sigma for terminal atoms of 0.01 within 3A
5. Others
 Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C16B)=Sof(N3B)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16A)=Sof(N3A)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C14(H14)
6.c Idealised Me refined as rotating group:
 C15(H15D,H15E,H15F), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.6209(2) 0.81926(17) 0.96768(14) 0.0229(3) Uani 1 1 d . . . . .
H1 H 0.705205 0.783504 1.012600 0.027 Uiso 1 1 calc R U . . .
C2 C 0.4704(2) 0.8292(2) 1.03309(16) 0.0294(4) Uani 1 1 d . . . . .
H2 H 0.451106 0.799657 1.121852 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3489(2) 0.8822(2) 0.96817(18) 0.0323(4) Uani 1 1 d . . . . .
H3 H 0.245157 0.893086 1.010753 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3799(2) 0.91948(19) 0.84005(17) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.296590 0.954395 0.793965 0.032 Uiso 1 1 calc R U . . .
C5 C 0.53272(18) 0.90593(16) 0.77859(14) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.56800(18) 0.93812(16) 0.64145(14) 0.0199(3) Uani 1 1 d . . . . .
H6A H 0.641346 1.019251 0.594478 0.024 Uiso 1 1 calc R U . . .
H6B H 0.467865 0.963960 0.608917 0.024 Uiso 1 1 calc R U . . .
C7 C 0.64296(18) 0.81468(17) 0.61810(15) 0.0204(3) Uani 1 1 d . . . . .
H7A H 0.584653 0.728247 0.681155 0.025 Uiso 1 1 calc R U . . .
H7B H 0.632703 0.827881 0.533218 0.025 Uiso 1 1 calc R U . . .
C8 C 0.8704(2) 0.65414(16) 0.65027(15) 0.0211(3) Uani 1 1 d . . . . .
H8A H 0.825303 0.590217 0.738890 0.025 Uiso 1 1 calc R U . . .
H8B H 0.987855 0.652630 0.640266 0.025 Uiso 1 1 calc R U . . .
C9 C 0.82725(19) 0.59994(15) 0.56448(14) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.88243(19) 0.66882(16) 0.43367(15) 0.0200(3) Uani 1 1 d . . . . .
C11 C 0.8431(2) 0.61464(17) 0.35720(15) 0.0222(3) Uani 1 1 d . . . . .
C12 C 0.7507(2) 0.49543(17) 0.40631(16) 0.0244(3) Uani 1 1 d . . . . .
H12 H 0.724436 0.460168 0.352534 0.029 Uiso 1 1 calc R U . . .
C13 C 0.6979(2) 0.42924(16) 0.53535(16) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.7345(2) 0.48022(16) 0.61423(15) 0.0226(3) Uani 1 1 d . . . . .
H14 H 0.696173 0.433247 0.702845 0.027 Uiso 1 1 calc R U . . .
Cl1 Cl 0.96367(4) 0.94864(4) 0.87004(3) 0.02213(8) Uani 1 1 d . . . . .
Cl2 Cl 1.13620(4) 0.87402(4) 0.63518(4) 0.02408(8) Uani 1 1 d . . . . .
Cl3 Cl 0.91282(6) 0.70057(5) 0.19510(4) 0.03420(10) Uani 1 1 d . . . . .
Cl4 Cl 0.58152(6) 0.27932(5) 0.60044(5) 0.03493(10) Uani 1 1 d . . . . .
N1 N 0.65201(15) 0.85866(13) 0.84230(11) 0.0163(2) Uani 1 1 d . . . . .
N2 N 0.81293(15) 0.79838(13) 0.62630(12) 0.0158(2) Uani 1 1 d . . . . .
H2A H 0.865(2) 0.849(2) 0.5581(19) 0.023(5) Uiso 1 1 d . . . . .
O1 O 0.97235(16) 0.78472(13) 0.39133(11) 0.0265(3) Uani 1 1 d D . . . .
H1A H 0.981(3) 0.832(2) 0.3162(10) 0.048(7) Uiso 1 1 d D . . . .
Pd1 Pd 0.87998(2) 0.86509(2) 0.74599(2) 0.01469(4) Uani 1 1 d . . . . .
C15 C 0.1973(4) 0.5793(3) 0.9630(3) 0.0811(10) Uani 1 1 d D U . . .
H15D H 0.140047 0.638762 0.896052 0.122 Uiso 0.594(16) 1 calc R U P A 2
H15E H 0.207083 0.627872 1.014045 0.122 Uiso 0.594(16) 1 calc R U P A 2
H15F H 0.138309 0.491689 1.016811 0.122 Uiso 0.594(16) 1 calc R U P A 2
H15A H 0.157540 0.670126 0.908804 0.122 Uiso 0.406(16) 1 calc R U P A 1
H15B H 0.224729 0.584729 1.035672 0.122 Uiso 0.406(16) 1 calc R U P A 1
H15C H 0.114642 0.507984 0.992675 0.122 Uiso 0.406(16) 1 calc R U P A 1
C16A C 0.3370(16) 0.542(2) 0.8920(18) 0.064(2) Uani 0.406(16) 1 d D U P A 1
N3A N 0.4204(16) 0.5218(8) 0.8299(8) 0.067(2) Uani 0.406(16) 1 d . U P A 1
C16B C 0.3540(9) 0.5491(15) 0.9071(12) 0.063(2) Uani 0.594(16) 1 d D U P A 2
N3B N 0.4908(11) 0.5229(6) 0.8706(8) 0.082(2) Uani 0.594(16) 1 d . U P A 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 H1 0.9500 . ?
C1 C2 1.380(2) . ?
C1 N1 1.3445(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(2) . ?
C5 C6 1.493(2) . ?
C5 N1 1.3432(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.518(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N2 1.4756(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.504(2) . ?
C8 N2 1.4888(19) . ?
C9 C10 1.400(2) . ?
C9 C14 1.389(2) . ?
C10 C11 1.389(2) . ?
C10 O1 1.3542(19) . ?
C11 C12 1.384(2) . ?
C11 Cl3 1.7372(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(2) . ?
C13 C14 1.381(2) . ?
C13 Cl4 1.7376(17) . ?
C14 H14 0.9500 . ?
Cl1 Pd1 2.2991(4) . ?
Cl2 Pd1 2.2961(4) . ?
N1 Pd1 2.0355(12) . ?
N2 H2A 0.81(2) . ?
N2 Pd1 2.0599(13) . ?
O1 H1A 0.808(9) . ?
C15 H15D 0.9800 . ?
C15 H15E 0.9800 . ?
C15 H15F 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16A 1.441(3) . ?
C15 C16B 1.442(3) . ?
C16A N3A 0.999(10) . ?
C16B N3B 1.213(8) . ?

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
C2 C1 H1 119.0 . . ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 122.00(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.09(16) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 118.92(16) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.92(16) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.13(14) . . ?
N1 C5 C4 120.63(14) . . ?
N1 C5 C6 118.21(13) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C5 C6 C7 111.87(13) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N2 C7 C6 112.03(13) . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
N2 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
N2 C8 C9 114.14(12) . . ?
C10 C9 C8 120.14(14) . . ?
C14 C9 C8 120.44(14) . . ?
C14 C9 C10 119.41(15) . . ?
C11 C10 C9 118.77(14) . . ?
O1 C10 C9 116.46(14) . . ?
O1 C10 C11 124.77(14) . . ?
C10 C11 Cl3 118.38(12) . . ?
C12 C11 C10 122.03(15) . . ?
C12 C11 Cl3 119.59(13) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.22(15) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 C14 121.32(15) . . ?
C12 C13 Cl4 119.52(13) . . ?
C14 C13 Cl4 119.16(13) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.25(15) . . ?
C13 C14 H14 119.9 . . ?
C1 N1 Pd1 120.72(11) . . ?
C5 N1 C1 119.38(13) . . ?
C5 N1 Pd1 119.64(10) . . ?
C7 N2 C8 111.76(12) . . ?
C7 N2 H2A 108.4(14) . . ?
C7 N2 Pd1 116.31(9) . . ?
C8 N2 H2A 105.8(14) . . ?
C8 N2 Pd1 111.51(9) . . ?
Pd1 N2 H2A 102.1(14) . . ?
C10 O1 H1A 112.7(19) . . ?
Cl2 Pd1 Cl1 90.740(15) . . ?
N1 Pd1 Cl1 89.62(4) . . ?
N1 Pd1 Cl2 179.33(4) . . ?
N1 Pd1 N2 92.64(5) . . ?
N2 Pd1 Cl1 176.84(4) . . ?
N2 Pd1 Cl2 86.97(4) . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16A C15 H15A 109.5 . . ?
C16A C15 H15B 109.5 . . ?
C16A C15 H15C 109.5 . . ?
C16B C15 H15D 109.5 . . ?
C16B C15 H15E 109.5 . . ?
C16B C15 H15F 109.5 . . ?
N3A C16A C15 168(2) . . ?
N3B C16B C15 173.4(13) . . ?

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
_geom_hbond_publ_flag
N2 H2A O1 0.81(2) 2.37(2) 2.9138(18) 125.0(17) . yes
O1 H1A Cl1 0.808(9) 2.418(15) 3.1534(13) 152(2) 2_776 yes

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
C1 C2 C3 C4 2.2(3) . . . . ?
C2 C1 N1 C5 -1.7(2) . . . . ?
C2 C1 N1 Pd1 172.39(13) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 176.67(16) . . . . ?
C3 C4 C5 N1 -1.0(3) . . . . ?
C4 C5 C6 C7 -123.55(16) . . . . ?
C4 C5 N1 C1 2.5(2) . . . . ?
C4 C5 N1 Pd1 -171.62(12) . . . . ?
C5 C6 C7 N2 -76.91(16) . . . . ?
C6 C5 N1 C1 -175.18(14) . . . . ?
C6 C5 N1 Pd1 10.66(18) . . . . ?
C6 C7 N2 C8 159.25(13) . . . . ?
C6 C7 N2 Pd1 29.64(16) . . . . ?
C8 C9 C10 C11 178.75(14) . . . . ?
C8 C9 C10 O1 -0.9(2) . . . . ?
C8 C9 C14 C13 -178.69(14) . . . . ?
C9 C8 N2 C7 48.75(17) . . . . ?
C9 C8 N2 Pd1 -179.17(11) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C9 C10 C11 Cl3 -179.77(12) . . . . ?
C10 C9 C14 C13 0.3(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C11 C12 C13 Cl4 179.98(13) . . . . ?
C12 C13 C14 C9 -0.4(2) . . . . ?
C14 C9 C10 C11 -0.3(2) . . . . ?
C14 C9 C10 O1 -179.92(14) . . . . ?
Cl3 C11 C12 C13 179.70(13) . . . . ?
Cl4 C13 C14 C9 -179.96(12) . . . . ?
N1 C1 C2 C3 -0.7(3) . . . . ?
N1 C5 C6 C7 54.16(19) . . . . ?
N2 C8 C9 C10 61.0(2) . . . . ?
N2 C8 C9 C14 -119.96(16) . . . . ?
O1 C10 C11 C12 179.92(15) . . . . ?
O1 C10 C11 Cl3 -0.2(2) . . . . ?

####################################################################### 
# 
# 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_hadi0402
_database_code_depnum_ccdc_archive 'CCDC 2203865'
loop_
_audit_author_name
_audit_author_address
' Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2022-08-28 deposited with the CCDC.	2024-05-16 downloaded from the CCDC.
;

_audit_creation_date             2022-02-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 Br Cl3 N2 O Pd, C2 H3 N'
_chemical_formula_sum            'C16 H17 Br Cl3 N3 O Pd'
_chemical_formula_weight         559.98
_chemical_melting_point          ?

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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6207(2)
_cell_length_b                   10.6773(2)
_cell_length_c                   11.9875(3)
_cell_angle_alpha                114.694(2)
_cell_angle_beta                 98.595(2)
_cell_angle_gamma                96.125(2)
_cell_volume                     973.51(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17907
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      33.3210
_cell_measurement_theta_min      3.2200
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.458
_exptl_absorpt_coefficient_mu    3.427
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0781
-1 0 0 0.0721
0 -5 2 0.1015
-1 5 -3 0.1403
0 0 1 0.0348
0 0 -1 0.0138
-1 0 1 0.0696

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05

_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.150
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  64.00   0.50    1.40    --   10.95  57.00  60.00  138
  2  ω     -5.00  84.00   0.50    1.40    --   10.95  57.00 -60.00  178
  3  ω     -3.00  90.00   0.50    1.40    --   10.95  38.00-180.00  186
  4  ω    -43.00  14.00   0.50    1.40    --  -11.88  94.00  43.13  114
  5  ω    -28.00  61.00   0.50    1.40    --  -11.88  57.00  30.00  178
  6  ω    -35.00  62.00   0.50    1.40    --  -11.88  77.00-150.00  194
  7  ω    -90.00   4.00   0.50    1.40    --  -11.88 -38.00-120.00  188
  8  ω    -23.00  22.00   0.50    1.40    --  -11.88 -99.00-150.00   90
  9  ω    -23.00  22.00   0.50    1.40    --  -11.88 -99.00 -60.00   90
 10  ω    -23.00  22.00   0.50    1.40    --  -11.88 -99.00 150.00   90
 11  ω     11.00  59.00   0.50    1.40    --   10.95-124.00   7.00   96
 12  ω     14.00  62.00   0.50    1.40    --   10.95-129.00  41.58   96
 13  ω     39.00  90.00   0.50    1.40    --   10.95-178.00 -90.00  102
 14  ω     24.00  73.00   0.50    1.40    --   10.95-147.00-158.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0678443000
_diffrn_orient_matrix_UB_12      -0.0465801000
_diffrn_orient_matrix_UB_13      -0.0455443000
_diffrn_orient_matrix_UB_21      0.0418933000
_diffrn_orient_matrix_UB_22      -0.0077163000
_diffrn_orient_matrix_UB_23      -0.0484157000
_diffrn_orient_matrix_UB_31      0.0286542000
_diffrn_orient_matrix_UB_32      -0.0575614000
_diffrn_orient_matrix_UB_33      0.0052986000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5362
_reflns_number_total             5955
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5955
_refine_ls_number_restraints     65
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0557
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 N3A-C16A = N3B-C16B
 1.15 with sigma of 0.003
 C16B-C15 = C16A-C15
 1.45 with sigma of 0.003
 O1-H1A
 0.82 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C15 \\sim C16A \\sim N3A \\sim C16B \\sim N3B: within 3A with sigma of 0.005
and sigma for terminal atoms of 0.01 within 3A
4. Others
 Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C16B)=Sof(N3B)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16A)=Sof(N3A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C14(H14)
5.c Idealised Me refined as rotating group:
 C15(H15D,H15E,H15F), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.90606(3) 1.09964(2) 0.81116(2) 0.02914(5) Uani 1 1 d . . . . .
C1 C 0.6077(2) 0.2161(2) 0.03732(17) 0.0224(4) Uani 1 1 d . . . . .
H1 H 0.690104 0.207753 -0.008432 0.027 Uiso 1 1 calc R U . . .
C2 C 0.4567(2) 0.1384(2) -0.02550(19) 0.0288(4) Uani 1 1 d . . . . .
H2 H 0.435794 0.077819 -0.112990 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3366(2) 0.1497(2) 0.0405(2) 0.0312(5) Uani 1 1 d . . . . .
H3 H 0.232562 0.094981 -0.000073 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3708(2) 0.2424(2) 0.1668(2) 0.0266(4) Uani 1 1 d . . . . .
H4 H 0.289038 0.253624 0.213352 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5244(2) 0.31922(18) 0.22573(17) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.5622(2) 0.42421(18) 0.36057(17) 0.0205(3) Uani 1 1 d . . . . .
H6A H 0.636114 0.391911 0.409945 0.025 Uiso 1 1 calc R U . . .
H6B H 0.462719 0.430986 0.392915 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6380(2) 0.56852(18) 0.37857(19) 0.0216(4) Uani 1 1 d . . . . .
H7A H 0.579841 0.589568 0.312683 0.026 Uiso 1 1 calc R U . . .
H7B H 0.628146 0.640135 0.461243 0.026 Uiso 1 1 calc R U . . .
C8 C 0.8680(2) 0.69702(18) 0.34690(18) 0.0212(4) Uani 1 1 d . . . . .
H8A H 0.823347 0.673463 0.257983 0.025 Uiso 1 1 calc R U . . .
H8B H 0.985678 0.709382 0.358568 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8250(2) 0.83443(17) 0.42990(17) 0.0191(3) Uani 1 1 d . . . . .
C10 C 0.8778(2) 0.89359(18) 0.56049(17) 0.0192(3) Uani 1 1 d . . . . .
C11 C 0.8374(2) 1.02064(18) 0.63440(17) 0.0206(3) Uani 1 1 d . . . . .
C12 C 0.7462(2) 1.09036(19) 0.58189(19) 0.0233(4) Uani 1 1 d . . . . .
H12 H 0.719286 1.177026 0.633344 0.028 Uiso 1 1 calc R U . . .
C13 C 0.6962(2) 1.02974(19) 0.45280(19) 0.0230(4) Uani 1 1 d . . . . .
C14 C 0.7337(2) 0.90292(19) 0.37653(18) 0.0222(4) Uani 1 1 d . . . . .
H14 H 0.697024 0.862972 0.287922 0.027 Uiso 1 1 calc R U . . .
Cl1 Cl 0.95437(5) 0.19135(4) 0.13322(4) 0.02214(9) Uani 1 1 d . . . . .
Cl2 Cl 1.13155(5) 0.49510(5) 0.36480(4) 0.02449(9) Uani 1 1 d . . . . .
Cl3 Cl 0.58191(7) 1.11352(5) 0.38344(5) 0.03341(12) Uani 1 1 d . . . . .
N1 N 0.64246(18) 0.30359(15) 0.16133(14) 0.0171(3) Uani 1 1 d . . . . .
N2 N 0.80900(18) 0.57707(15) 0.37221(15) 0.0166(3) Uani 1 1 d . . . . .
H2A H 0.859(3) 0.592(2) 0.439(2) 0.019(6) Uiso 1 1 d . . . . .
O1 O 0.96576(18) 0.82005(14) 0.60520(13) 0.0247(3) Uani 1 1 d D . . . .
H1A H 0.988(3) 0.851(3) 0.6808(10) 0.040(8) Uiso 1 1 d D . . . .
Pd1 Pd 0.87258(2) 0.39423(2) 0.25527(2) 0.01447(4) Uani 1 1 d . . . . .
C15 C 0.8068(5) 0.5389(5) -0.0366(4) 0.0949(13) Uani 1 1 d D U . . .
H15D H 0.857568 0.576880 -0.086728 0.142 Uiso 0.454(9) 1 calc R U P A 2
H15E H 0.883517 0.498920 0.001346 0.142 Uiso 0.454(9) 1 calc R U P A 2
H15F H 0.771896 0.614344 0.029793 0.142 Uiso 0.454(9) 1 calc R U P A 2
H15A H 0.852395 0.526111 -0.109971 0.142 Uiso 0.546(9) 1 calc R U P A 1
H15B H 0.871013 0.504735 0.015459 0.142 Uiso 0.546(9) 1 calc R U P A 1
H15C H 0.806749 0.638824 0.012706 0.142 Uiso 0.546(9) 1 calc R U P A 1
C16A C 0.6438(7) 0.4605(12) -0.0784(10) 0.091(2) Uani 0.546(9) 1 d D U P A 1
N3A N 0.5088(6) 0.4131(10) -0.1072(9) 0.102(2) Uani 0.546(9) 1 d D U P A 1
C16B C 0.6718(13) 0.4321(11) -0.1158(11) 0.085(2) Uani 0.454(9) 1 d D U P A 2
N3B N 0.5803(11) 0.3333(8) -0.1808(8) 0.094(2) Uani 0.454(9) 1 d D U P A 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
Br1 C11 1.8913(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(3) . ?
C1 N1 1.349(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.492(3) . ?
C5 N1 1.350(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N2 1.482(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.512(2) . ?
C8 N2 1.491(2) . ?
C9 C10 1.399(3) . ?
C9 C14 1.388(3) . ?
C10 C11 1.391(2) . ?
C10 O1 1.355(2) . ?
C11 C12 1.391(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 C14 1.386(3) . ?
C13 Cl3 1.7397(19) . ?
C14 H14 0.9500 . ?
Cl1 Pd1 2.3057(4) . ?
Cl2 Pd1 2.3015(5) . ?
N1 Pd1 2.0377(15) . ?
N2 H2A 0.79(2) . ?
N2 Pd1 2.0611(14) . ?
O1 H1A 0.808(10) . ?
C15 H15D 0.9800 . ?
C15 H15E 0.9800 . ?
C15 H15F 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C16A 1.454(3) . ?
C15 C16B 1.428(3) . ?
C16A N3A 1.157(3) . ?
C16B N3B 1.137(3) . ?

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
C2 C1 H1 118.8 . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.37(19) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.12(19) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.61(19) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.15(19) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.98(17) . . ?
N1 C5 C4 120.75(17) . . ?
N1 C5 C6 118.24(16) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C5 C6 C7 111.93(16) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N2 C7 C6 111.88(14) . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
N2 C8 H8A 108.7 . . ?
N2 C8 H8B 108.7 . . ?
N2 C8 C9 114.11(15) . . ?
C10 C9 C8 120.27(16) . . ?
C14 C9 C8 120.02(17) . . ?
C14 C9 C10 119.72(16) . . ?
C11 C10 C9 118.97(16) . . ?
O1 C10 C9 116.10(15) . . ?
O1 C10 C11 124.93(17) . . ?
C10 C11 Br1 119.10(14) . . ?
C10 C11 C12 121.80(17) . . ?
C12 C11 Br1 119.10(14) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 117.95(17) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 C14 121.70(17) . . ?
C12 C13 Cl3 119.39(14) . . ?
C14 C13 Cl3 118.91(15) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.86(18) . . ?
C13 C14 H14 120.1 . . ?
C1 N1 C5 118.94(16) . . ?
C1 N1 Pd1 120.92(13) . . ?
C5 N1 Pd1 119.78(12) . . ?
C7 N2 C8 111.45(14) . . ?
C7 N2 H2A 108.2(17) . . ?
C7 N2 Pd1 116.11(11) . . ?
C8 N2 H2A 106.4(17) . . ?
C8 N2 Pd1 111.60(11) . . ?
Pd1 N2 H2A 102.2(16) . . ?
C10 O1 H1A 115(2) . . ?
Cl2 Pd1 Cl1 90.526(17) . . ?
N1 Pd1 Cl1 89.59(4) . . ?
N1 Pd1 Cl2 178.72(4) . . ?
N1 Pd1 N2 92.94(6) . . ?
N2 Pd1 Cl1 176.95(5) . . ?
N2 Pd1 Cl2 86.91(4) . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16A C15 H15A 109.5 . . ?
C16A C15 H15B 109.5 . . ?
C16A C15 H15C 109.5 . . ?
C16B C15 H15D 109.5 . . ?
C16B C15 H15E 109.5 . . ?
C16B C15 H15F 109.5 . . ?
N3A C16A C15 172.0(12) . . ?
N3B C16B C15 169.5(15) . . ?

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
_geom_hbond_publ_flag
N2 H2A O1 0.79(2) 2.38(2) 2.903(2) 124(2) . yes
O1 H1A Cl1 0.808(10) 2.443(16) 3.1644(15) 149(3) 2_766 yes

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
Br1 C11 C12 C13 -179.31(15) . . . . ?
C1 C2 C3 C4 2.1(3) . . . . ?
C2 C1 N1 C5 -2.2(3) . . . . ?
C2 C1 N1 Pd1 170.99(15) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 177.39(19) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
C4 C5 C6 C7 -124.85(19) . . . . ?
C4 C5 N1 C1 2.6(3) . . . . ?
C4 C5 N1 Pd1 -170.65(14) . . . . ?
C5 C6 C7 N2 -77.7(2) . . . . ?
C6 C5 N1 C1 -175.55(16) . . . . ?
C6 C5 N1 Pd1 11.2(2) . . . . ?
C6 C7 N2 C8 160.97(15) . . . . ?
C6 C7 N2 Pd1 31.7(2) . . . . ?
C8 C9 C10 C11 179.54(17) . . . . ?
C8 C9 C10 O1 -0.7(3) . . . . ?
C8 C9 C14 C13 -179.20(17) . . . . ?
C9 C8 N2 C7 48.4(2) . . . . ?
C9 C8 N2 Pd1 179.99(12) . . . . ?
C9 C10 C11 Br1 179.11(13) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C9 C14 C13 0.3(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C11 C12 C13 Cl3 179.97(15) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C14 C9 C10 C11 0.0(3) . . . . ?
C14 C9 C10 O1 179.77(17) . . . . ?
Cl3 C13 C14 C9 179.89(14) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
N1 C5 C6 C7 53.3(2) . . . . ?
N2 C8 C9 C10 60.2(2) . . . . ?
N2 C8 C9 C14 -120.24(19) . . . . ?
O1 C10 C11 Br1 -0.6(3) . . . . ?
O1 C10 C11 C12 -179.89(18) . . . . ?

