# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_i16265
_database_code_depnum_ccdc_archive 'CCDC 1948936'
loop_
_audit_author_name
_audit_author_address
'Norman Lu'
;Institute of Organic and Polymeric Materials, National Taipei University of Technology
Taiwan
;
_audit_update_record             
;
2019-08-23 deposited with the CCDC.	2019-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          411.15
_chemical_formula_moiety         'C18 H18 Cl2 F8 N2 O2 Pd'
_chemical_formula_sum            'C18 H18 Cl2 F8 N2 O2 Pd'
_chemical_formula_weight         623.64

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'
F F 0.0171 0.0103 '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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.0691(2)
_cell_length_b                   18.6278(5)
_cell_length_c                   8.7985(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.6250(10)
_cell_angle_gamma                90
_cell_volume                     1091.30(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    6271
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.12

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.182
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8436
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   'Bruker SADABS, 1996'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(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            11039
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2398
_reflns_number_gt                2195
_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 Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0137P)²+0.6841P] 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     SHELXL
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2398
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0498
_refine_ls_wR_factor_gt          0.0479
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.5000 0.5000 1.0000 0.00780(7) Uani 1 2 d S . P . .
Cl1 Cl 0.77495(6) 0.56218(2) 1.16485(5) 0.01241(11) Uani 1 1 d . . . . .
F1 F 0.16602(17) 0.62555(6) -0.04913(13) 0.0181(2) Uani 1 1 d . . . . .
F2 F 0.07357(17) 0.73832(6) -0.08363(13) 0.0195(3) Uani 1 1 d . . . . .
F3 F 0.43022(19) 0.71022(7) -0.12084(15) 0.0262(3) Uani 1 1 d . . . . .
F4 F 0.45122(17) 0.78113(6) 0.08116(14) 0.0213(3) Uani 1 1 d . . . . .
O1 O 0.30192(18) 0.64571(7) 0.28297(15) 0.0113(3) Uani 1 1 d . . . . .
N1 N 0.5549(2) 0.53722(8) 0.80331(18) 0.0096(3) Uani 1 1 d . . . . .
C1 C 0.4122(3) 0.57321(10) 0.6895(2) 0.0101(4) Uani 1 1 d . . . . .
H1 H 0.2860 0.5802 0.7036 0.012 Uiso 1 1 calc R U . . .
C2 C 0.4400(3) 0.60077(10) 0.5520(2) 0.0102(4) Uani 1 1 d . . . . .
C3 C 0.6246(3) 0.58880(10) 0.5314(2) 0.0116(4) Uani 1 1 d . . . . .
H3 H 0.6494 0.6063 0.4385 0.014 Uiso 1 1 calc R U . . .
C4 C 0.7708(3) 0.55110(10) 0.6485(2) 0.0127(4) Uani 1 1 d . . . . .
H4 H 0.8972 0.5423 0.6360 0.015 Uiso 1 1 calc R U . . .
C5 C 0.7339(3) 0.52619(10) 0.7835(2) 0.0110(4) Uani 1 1 d . . . . .
H5 H 0.8362 0.5008 0.8638 0.013 Uiso 1 1 calc R U . . .
C6 C 0.2737(3) 0.64311(10) 0.4354(2) 0.0130(4) Uani 1 1 d . . . . .
H6A H 0.1429 0.6204 0.4236 0.016 Uiso 1 1 calc R U . . .
H6B H 0.2726 0.6924 0.4770 0.016 Uiso 1 1 calc R U . . .
C7 C 0.1645(3) 0.69345(10) 0.1769(2) 0.0116(4) Uani 1 1 d . . . . .
H7A H 0.1837 0.7427 0.2221 0.014 Uiso 1 1 calc R U . . .
H7B H 0.0249 0.6783 0.1607 0.014 Uiso 1 1 calc R U . . .
C8 C 0.2039(3) 0.69182(10) 0.0193(2) 0.0124(4) Uani 1 1 d . . . . .
C9 C 0.4170(3) 0.71220(11) 0.0300(2) 0.0160(4) Uani 1 1 d . . . . .
H9 H 0.5175 0.6792 0.1045 0.019 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 2.0192(14) 3_667 ?
Pd1 N1 2.0192(14) . ?
Pd1 Cl1 2.3086(4) 3_667 ?
Pd1 Cl1 2.3086(4) . ?
F1 C8 1.360(2) . ?
F2 C8 1.363(2) . ?
F3 C9 1.361(2) . ?
F4 C9 1.355(2) . ?
O1 C7 1.413(2) . ?
O1 C6 1.422(2) . ?
N1 C1 1.338(2) . ?
N1 C5 1.350(2) . ?
C1 C2 1.388(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(2) . ?
C2 C6 1.499(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.503(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(3) . ?
C9 H9 1.0000 . ?

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 N1 180.00(7) 3_667 . ?
N1 Pd1 Cl1 90.15(4) 3_667 3_667 ?
N1 Pd1 Cl1 89.85(4) . 3_667 ?
N1 Pd1 Cl1 89.85(4) 3_667 . ?
N1 Pd1 Cl1 90.15(4) . . ?
Cl1 Pd1 Cl1 180.0 3_667 . ?
C7 O1 C6 111.19(13) . . ?
C1 N1 C5 118.90(15) . . ?
C1 N1 Pd1 119.97(11) . . ?
C5 N1 Pd1 121.13(12) . . ?
N1 C1 C2 123.06(16) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 117.83(16) . . ?
C1 C2 C6 118.88(15) . . ?
C3 C2 C6 123.28(16) . . ?
C4 C3 C2 118.90(16) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 120.18(16) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 121.12(17) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
O1 C6 C2 109.71(14) . . ?
O1 C6 H6A 109.7 . . ?
C2 C6 H6A 109.7 . . ?
O1 C6 H6B 109.7 . . ?
C2 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
O1 C7 C8 107.29(14) . . ?
O1 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
O1 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
F1 C8 F2 107.10(14) . . ?
F1 C8 C7 110.91(15) . . ?
F2 C8 C7 107.87(14) . . ?
F1 C8 C9 107.23(14) . . ?
F2 C8 C9 108.40(15) . . ?
C7 C8 C9 115.04(15) . . ?
F4 C9 F3 106.66(15) . . ?
F4 C9 C8 108.56(15) . . ?
F3 C9 C8 108.84(16) . . ?
F4 C9 H9 110.9 . . ?
F3 C9 H9 110.9 . . ?
C8 C9 H9 110.9 . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dimethyl sulfoxide, water'
####################################################################### 
# 
# 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_i16264
_database_code_depnum_ccdc_archive 'CCDC 1948937'
loop_
_audit_author_name
_audit_author_address
'Norman Lu'
;Institute of Organic and Polymeric Materials, National Taipei University of Technology
Taiwan
;
_audit_update_record             
;
2019-08-23 deposited with the CCDC.	2019-10-15 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          414.15
_chemical_formula_moiety         'C18 H18 Br2 F8 N2 O2 Pd'
_chemical_formula_sum            'C18 H18 Br2 F8 N2 O2 Pd'
_chemical_formula_weight         712.56

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'
F F 0.0171 0.0103 '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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.2992(3)
_cell_length_b                   18.6059(7)
_cell_length_c                   8.7965(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.215(2)
_cell_angle_gamma                90
_cell_volume                     1121.05(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9029
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.25

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.111
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    4.477
_shelx_estimated_absorpt_T_min   0.413
_shelx_estimated_absorpt_T_max   0.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(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            27252
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.189
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2473
_reflns_number_gt                2394
_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 Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0122P)²+0.9744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2473
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0163
_refine_ls_R_factor_gt           0.0153
_refine_ls_wR_factor_ref         0.0373
_refine_ls_wR_factor_gt          0.0370
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.002
_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 0.500000 0.500000 1.000000 0.00860(5) Uani 1 2 d S . P . .
Br1 Br 0.78386(2) 0.56560(2) 1.17324(2) 0.01281(5) Uani 1 1 d . . . . .
F1 F 0.08337(15) 0.74066(6) -0.08384(12) 0.0192(2) Uani 1 1 d . . . . .
F2 F 0.17771(15) 0.62858(5) -0.04384(12) 0.0192(2) Uani 1 1 d . . . . .
F3 F 0.44777(16) 0.78627(6) 0.08041(13) 0.0210(2) Uani 1 1 d . . . . .
F4 F 0.43060(18) 0.71319(6) -0.11738(14) 0.0270(3) Uani 1 1 d . . . . .
O1 O 0.30429(16) 0.64904(6) 0.28581(14) 0.0123(2) Uani 1 1 d . . . . .
N1 N 0.55005(19) 0.53741(7) 0.80269(16) 0.0108(3) Uani 1 1 d . . . . .
C1 C 0.4124(2) 0.57560(8) 0.6911(2) 0.0111(3) Uani 1 1 d . . . . .
H1 H 0.293(3) 0.5820(11) 0.712(2) 0.013 Uiso 1 1 d . U . . .
C2 C 0.4395(2) 0.60361(8) 0.5547(2) 0.0110(3) Uani 1 1 d . . . . .
C3 C 0.6159(2) 0.59048(9) 0.5320(2) 0.0123(3) Uani 1 1 d . . . . .
H3 H 0.636(3) 0.6082(11) 0.437(2) 0.015 Uiso 1 1 d . U . . .
C4 C 0.7565(2) 0.55036(9) 0.6469(2) 0.0136(3) Uani 1 1 d . . . . .
H4 H 0.877(3) 0.5408(11) 0.634(2) 0.016 Uiso 1 1 d . U . . .
C5 C 0.7213(2) 0.52491(9) 0.7810(2) 0.0121(3) Uani 1 1 d . . . . .
H5 H 0.813(3) 0.4988(10) 0.858(3) 0.014 Uiso 1 1 d . U . . .
C6 C 0.2796(2) 0.64784(9) 0.4392(2) 0.0128(3) Uani 1 1 d . . . . .
H6A H 0.289(3) 0.6960(11) 0.479(2) 0.015 Uiso 1 1 d . U . . .
H6B H 0.154(3) 0.6273(11) 0.428(2) 0.015 Uiso 1 1 d . U . . .
C7 C 0.1741(2) 0.69788(9) 0.1795(2) 0.0123(3) Uani 1 1 d . . . . .
H7A H 0.038(3) 0.6840(11) 0.158(2) 0.015 Uiso 1 1 d . U . . .
H7B H 0.199(3) 0.7456(11) 0.219(2) 0.015 Uiso 1 1 d . U . . .
C8 C 0.2122(2) 0.69554(9) 0.0223(2) 0.0129(3) Uani 1 1 d . . . . .
C9 C 0.4173(3) 0.71676(9) 0.0326(2) 0.0163(3) Uani 1 1 d . . . . .
H9 H 0.514(3) 0.6861(11) 0.106(3) 0.020 Uiso 1 1 d . 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 2.0171(13) . ?
Pd1 N1 2.0171(13) 3_667 ?
Pd1 Br1 2.43372(17) . ?
Pd1 Br1 2.43376(17) 3_667 ?
F1 C8 1.3617(18) . ?
F2 C8 1.3612(19) . ?
F3 C9 1.354(2) . ?
F4 C9 1.358(2) . ?
O1 C7 1.4104(19) . ?
O1 C6 1.4217(19) . ?
N1 C1 1.340(2) . ?
N1 C5 1.348(2) . ?
C1 C2 1.384(2) . ?
C1 H1 0.96(2) . ?
C2 C3 1.391(2) . ?
C2 C6 1.501(2) . ?
C3 C4 1.384(2) . ?
C3 H3 0.95(2) . ?
C4 C5 1.375(2) . ?
C4 H4 0.94(2) . ?
C5 H5 0.91(2) . ?
C6 H6A 0.96(2) . ?
C6 H6B 0.97(2) . ?
C7 C8 1.502(2) . ?
C7 H7A 0.98(2) . ?
C7 H7B 0.95(2) . ?
C8 C9 1.520(2) . ?
C9 H9 0.96(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 Pd1 N1 180.00(7) . 3_667 ?
N1 Pd1 Br1 89.86(4) . . ?
N1 Pd1 Br1 90.14(4) 3_667 . ?
N1 Pd1 Br1 90.14(4) . 3_667 ?
N1 Pd1 Br1 89.86(4) 3_667 3_667 ?
Br1 Pd1 Br1 180.0 . 3_667 ?
C7 O1 C6 111.25(12) . . ?
C1 N1 C5 119.01(14) . . ?
C1 N1 Pd1 120.03(11) . . ?
C5 N1 Pd1 120.96(11) . . ?
N1 C1 C2 122.62(15) . . ?
N1 C1 H1 115.1(12) . . ?
C2 C1 H1 122.2(12) . . ?
C1 C2 C3 118.38(15) . . ?
C1 C2 C6 118.86(15) . . ?
C3 C2 C6 122.76(15) . . ?
C4 C3 C2 118.65(15) . . ?
C4 C3 H3 121.6(12) . . ?
C2 C3 H3 119.8(12) . . ?
C5 C4 C3 120.07(15) . . ?
C5 C4 H4 119.8(13) . . ?
C3 C4 H4 120.1(12) . . ?
N1 C5 C4 121.26(15) . . ?
N1 C5 H5 118.0(13) . . ?
C4 C5 H5 120.8(13) . . ?
O1 C6 C2 109.09(13) . . ?
O1 C6 H6A 108.5(12) . . ?
C2 C6 H6A 109.0(12) . . ?
O1 C6 H6B 109.7(12) . . ?
C2 C6 H6B 109.9(12) . . ?
H6A C6 H6B 110.5(17) . . ?
O1 C7 C8 107.17(13) . . ?
O1 C7 H7A 111.4(12) . . ?
C8 C7 H7A 108.1(12) . . ?
O1 C7 H7B 111.0(12) . . ?
C8 C7 H7B 107.1(12) . . ?
H7A C7 H7B 111.7(16) . . ?
F2 C8 F1 106.82(13) . . ?
F2 C8 C7 110.73(14) . . ?
F1 C8 C7 108.02(13) . . ?
F2 C8 C9 107.24(13) . . ?
F1 C8 C9 108.28(13) . . ?
C7 C8 C9 115.41(14) . . ?
F3 C9 F4 106.81(14) . . ?
F3 C9 C8 108.63(14) . . ?
F4 C9 C8 109.19(15) . . ?
F3 C9 H9 110.8(13) . . ?
F4 C9 H9 110.0(13) . . ?
C8 C9 H9 111.3(12) . . ?

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.064


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dimethyl sulfoxide, Water'
