# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1584103'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 Br2 Cl0 N4 O2 Pd'
_chemical_formula_weight         740.77

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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   40.319(5)
_cell_length_b                   8.136(5)
_cell_length_c                   8.974(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2944(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8695
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.4

_exptl_crystal_description       needle
_exptl_crystal_colour            paleyellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    3.379
_shelx_estimated_absorpt_T_min   0.723
_shelx_estimated_absorpt_T_max   0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_T_max  0.7251
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            82760
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.484
_diffrn_reflns_theta_max         28.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7309
_reflns_number_gt                6555
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.993

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+2.4602P] 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_abs_structure_details 
;
 Flack x determined using 2661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.053(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7309
_refine_ls_number_parameters     352
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.08739(2) 0.72333(4) -0.10649(5) 0.03567(9) Uani 1 1 d . . . . .
Br2 Br 0.05702(2) 0.86839(7) -0.29887(8) 0.05509(16) Uani 1 1 d . . . . .
Br1 Br 0.12049(2) 0.56937(10) 0.07155(7) 0.0667(2) Uani 1 1 d . . . . .
N2 N 0.11877(10) 0.5448(5) -0.3625(5) 0.0347(9) Uani 1 1 d . . . . .
N1 N 0.20902(11) 1.0334(5) -0.5432(5) 0.0418(10) Uani 1 1 d . . . . .
N3 N 0.08308(11) 0.3961(5) -0.2475(5) 0.0422(10) Uani 1 1 d . . . . .
C18 C 0.14067(12) 0.6752(6) -0.4066(6) 0.0343(10) Uani 1 1 d . . . . .
O1 O 0.16771(10) 1.1809(5) -0.6490(6) 0.0618(12) Uani 1 1 d . . . . .
C14 C 0.17646(14) 0.8973(7) -0.3497(6) 0.0457(13) Uani 1 1 d . . . . .
H14 H 0.1854 0.9701 -0.2805 0.055 Uiso 1 1 calc R U . . .
O2 O 0.24949(12) 0.8939(6) -0.4232(8) 0.0837(17) Uani 1 1 d . . . . .
N4 N 0.07639(10) 0.9028(5) 0.0532(6) 0.0412(10) Uani 1 1 d . . . . .
C17 C 0.15474(13) 0.7769(6) -0.3036(6) 0.0422(11) Uani 1 1 d . . . . .
H17 H 0.1497 0.7651 -0.2030 0.051 Uiso 1 1 calc R U . . .
C5 C 0.26626(14) 1.1313(7) -0.5534(6) 0.0446(13) Uani 1 1 d . . . . .
C30 C 0.03688(18) 1.0573(9) 0.1910(9) 0.070(2) Uani 1 1 d . . . . .
H30 H 0.0148 1.0870 0.2053 0.084 Uiso 1 1 calc R U . . .
C15 C 0.17125(15) 0.8087(7) -0.5975(8) 0.0557(14) Uani 1 1 d . . . . .
H15 H 0.1771 0.8176 -0.6974 0.067 Uiso 1 1 calc R U . . .
C19 C 0.11835(14) 0.3920(7) -0.4307(7) 0.0476(13) Uani 1 1 d . . . . .
H19 H 0.1311 0.3594 -0.5118 0.057 Uiso 1 1 calc R U . . .
C22 C 0.05665(15) 0.3436(8) -0.1481(7) 0.0564(16) Uani 1 1 d . . . . .
H22A H 0.0602 0.3912 -0.0503 0.068 Uiso 1 1 calc R U . . .
H22B H 0.0573 0.2250 -0.1379 0.068 Uiso 1 1 calc R U . . .
C13 C 0.18506(13) 0.9106(6) -0.4977(6) 0.0398(11) Uani 1 1 d . . . . .
C3 C 0.22171(15) 1.2884(6) -0.6731(7) 0.0470(13) Uani 1 1 d . . . . .
C16 C 0.14844(17) 0.6903(8) -0.5544(7) 0.0556(16) Uani 1 1 d . . . . .
H16 H 0.1386 0.6222 -0.6249 0.067 Uiso 1 1 calc R U . . .
C7 C 0.32242(16) 1.2298(10) -0.5671(9) 0.071(2) Uani 1 1 d . . . . .
H7 H 0.3446 1.2179 -0.5416 0.085 Uiso 1 1 calc R U . . .
C2 C 0.19719(13) 1.1678(6) -0.6241(7) 0.0424(11) Uani 1 1 d . . . . .
C12 C 0.21138(18) 1.4213(8) -0.7563(8) 0.0636(18) Uani 1 1 d . . . . .
H12 H 0.1890 1.4356 -0.7776 0.076 Uiso 1 1 calc R U . . .
C23 C 0.02191(18) 0.3959(10) -0.2067(9) 0.074(2) Uani 1 1 d . . . . .
H23A H 0.0215 0.5142 -0.2198 0.089 Uiso 1 1 calc R U . . .
H23B H 0.0181 0.3457 -0.3033 0.089 Uiso 1 1 calc R U . . .
C4 C 0.25513(15) 1.2649(7) -0.6413(6) 0.0466(14) Uani 1 1 d . . . . .
C9 C 0.27909(18) 1.3823(9) -0.6934(8) 0.0618(18) Uani 1 1 d . . . . .
C11 C 0.2348(2) 1.5346(9) -0.8085(11) 0.084(2) Uani 1 1 d . . . . .
H11 H 0.2279 1.6233 -0.8661 0.100 Uiso 1 1 calc R U . . .
C6 C 0.29913(15) 1.1142(8) -0.5173(8) 0.0566(16) Uani 1 1 d . . . . .
H6 H 0.3060 1.0256 -0.4596 0.068 Uiso 1 1 calc R U . . .
C24 C -0.00491(18) 0.3477(11) -0.1050(12) 0.089(2) Uani 1 1 d . . . . .
H24A H 0.0000 0.3886 -0.0059 0.107 Uiso 1 1 calc R U . . .
H24B H -0.0060 0.2287 -0.0998 0.107 Uiso 1 1 calc R U . . .
C29 C 0.0607(2) 1.1210(11) 0.2788(11) 0.098(3) Uani 1 1 d . . . . .
H29 H 0.0555 1.1916 0.3569 0.117 Uiso 1 1 calc R U . . .
C10 C 0.2672(2) 1.5162(9) -0.7759(10) 0.079(2) Uani 1 1 d . . . . .
H10 H 0.2822 1.5949 -0.8094 0.094 Uiso 1 1 calc R U . . .
C20 C 0.09660(12) 0.5485(6) -0.2492(6) 0.0345(10) Uani 1 1 d . . . . .
C27 C 0.04522(14) 0.9483(8) 0.0805(8) 0.0516(14) Uani 1 1 d . . . . .
H27 H 0.0284 0.9042 0.0221 0.062 Uiso 1 1 calc R U . . .
C25 C 0.09992(17) 0.9691(9) 0.1379(9) 0.074(2) Uani 1 1 d . . . . .
H25 H 0.1219 0.9400 0.1209 0.089 Uiso 1 1 calc R U . . .
C21 C 0.09647(15) 0.3016(7) -0.3587(7) 0.0500(14) Uani 1 1 d . . . . .
H21 H 0.0911 0.1929 -0.3797 0.060 Uiso 1 1 calc R U . . .
C28 C 0.0929(2) 1.0783(12) 0.2489(13) 0.112(4) Uani 1 1 d . . . . .
H28 H 0.1101 1.1239 0.3044 0.134 Uiso 1 1 calc R U . . .
C1 C 0.24224(14) 1.0092(7) -0.5000(7) 0.0490(14) Uani 1 1 d . . . . .
C8 C 0.31267(18) 1.3590(10) -0.6525(9) 0.073(2) Uani 1 1 d . . . . .
H8 H 0.3285 1.4341 -0.6850 0.087 Uiso 1 1 calc R U . . .
C32 C -0.0379(2) 0.4130(13) -0.1543(15) 0.118(4) Uani 1 1 d . . . . .
H32A H -0.0547 0.3789 -0.0851 0.177 Uiso 1 1 calc R U . . .
H32B H -0.0371 0.5309 -0.1577 0.177 Uiso 1 1 calc R U . . .
H32C H -0.0431 0.3710 -0.2516 0.177 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 C20 1.950(5) . ?
Pd1 N4 2.094(4) . ?
Pd1 Br2 2.4234(11) . ?
Pd1 Br1 2.4295(10) . ?
N2 C20 1.354(7) . ?
N2 C19 1.385(7) . ?
N2 C18 1.436(6) . ?
N1 C2 1.397(7) . ?
N1 C1 1.408(7) . ?
N1 C13 1.448(6) . ?
N3 C20 1.355(6) . ?
N3 C21 1.371(8) . ?
N3 C22 1.454(7) . ?
C18 C17 1.364(7) . ?
C18 C16 1.368(8) . ?
O1 C2 1.214(6) . ?
C14 C17 1.378(7) . ?
C14 C13 1.377(8) . ?
O2 C1 1.200(7) . ?
N4 C27 1.333(7) . ?
N4 C25 1.330(8) . ?
C5 C6 1.371(8) . ?
C5 C4 1.416(8) . ?
C5 C1 1.468(7) . ?
C30 C29 1.347(12) . ?
C30 C27 1.372(9) . ?
C15 C13 1.342(8) . ?
C15 C16 1.387(8) . ?
C19 C21 1.318(8) . ?
C22 C23 1.555(10) . ?
C3 C12 1.378(9) . ?
C3 C4 1.390(8) . ?
C3 C2 1.461(7) . ?
C7 C8 1.359(11) . ?
C7 C6 1.402(9) . ?
C12 C11 1.400(10) . ?
C23 C24 1.468(10) . ?
C4 C9 1.436(8) . ?
C9 C10 1.402(11) . ?
C9 C8 1.415(10) . ?
C11 C10 1.350(11) . ?
C24 C32 1.500(12) . ?
C29 C28 1.371(12) . ?
C25 C28 1.364(11) . ?

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
C20 Pd1 N4 177.3(2) . . ?
C20 Pd1 Br2 89.05(15) . . ?
N4 Pd1 Br2 92.34(14) . . ?
C20 Pd1 Br1 87.21(15) . . ?
N4 Pd1 Br1 91.49(14) . . ?
Br2 Pd1 Br1 175.66(3) . . ?
C20 N2 C19 110.1(4) . . ?
C20 N2 C18 126.6(4) . . ?
C19 N2 C18 123.3(4) . . ?
C2 N1 C1 125.2(4) . . ?
C2 N1 C13 117.3(4) . . ?
C1 N1 C13 117.4(4) . . ?
C20 N3 C21 110.3(5) . . ?
C20 N3 C22 124.8(5) . . ?
C21 N3 C22 124.8(5) . . ?
C17 C18 C16 120.5(5) . . ?
C17 C18 N2 121.1(5) . . ?
C16 C18 N2 118.3(5) . . ?
C17 C14 C13 120.4(5) . . ?
C27 N4 C25 117.1(5) . . ?
C27 N4 Pd1 121.3(4) . . ?
C25 N4 Pd1 121.5(4) . . ?
C18 C17 C14 119.5(5) . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 C1 119.5(6) . . ?
C4 C5 C1 119.5(5) . . ?
C29 C30 C27 119.8(6) . . ?
C13 C15 C16 121.3(6) . . ?
C21 C19 N2 107.0(5) . . ?
N3 C22 C23 111.9(5) . . ?
C15 C13 C14 119.4(5) . . ?
C15 C13 N1 121.0(5) . . ?
C14 C13 N1 119.6(5) . . ?
C12 C3 C4 120.8(6) . . ?
C12 C3 C2 119.0(6) . . ?
C4 C3 C2 120.1(5) . . ?
C18 C16 C15 119.0(5) . . ?
C8 C7 C6 120.3(7) . . ?
O1 C2 N1 119.9(5) . . ?
O1 C2 C3 123.3(5) . . ?
N1 C2 C3 116.8(5) . . ?
C3 C12 C11 119.6(7) . . ?
C24 C23 C22 112.3(7) . . ?
C3 C4 C5 121.8(5) . . ?
C3 C4 C9 119.6(6) . . ?
C5 C4 C9 118.6(6) . . ?
C10 C9 C8 124.6(6) . . ?
C10 C9 C4 117.3(7) . . ?
C8 C9 C4 118.0(7) . . ?
C10 C11 C12 120.5(8) . . ?
C5 C6 C7 120.3(7) . . ?
C23 C24 C32 112.1(9) . . ?
C30 C29 C28 117.7(7) . . ?
C11 C10 C9 122.1(7) . . ?
N2 C20 N3 104.7(4) . . ?
N2 C20 Pd1 129.5(4) . . ?
N3 C20 Pd1 125.7(4) . . ?
N4 C27 C30 122.9(6) . . ?
N4 C25 C28 122.3(7) . . ?
C19 C21 N3 107.9(5) . . ?
C25 C28 C29 120.2(8) . . ?
O2 C1 N1 119.9(5) . . ?
O2 C1 C5 123.8(6) . . ?
N1 C1 C5 116.3(5) . . ?
C7 C8 C9 121.8(6) . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.081



