# Electronic Supplementary Material (ESI) for ChemComm.
# 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_15hhe10a
_database_code_depnum_ccdc_archive 'CCDC 1897642'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Eastern Illinois University
United States of America
;
_audit_update_record             
;
2019-02-17 deposited with the CCDC.	2019-03-28 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            'C38 H34 B2 Cl2 F4 N6 Pd'
_chemical_formula_weight         849.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
B B 0.0090 0.0039 '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'
F F 0.0727 0.0534 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   19.3737(4)
_cell_length_b                   10.1392(2)
_cell_length_c                   18.4928(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.3090(10)
_cell_angle_gamma                90
_cell_volume                     3632.56(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      4.645
_cell_measurement_theta_max      68.183

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             1720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    5.972
_shelx_estimated_absorpt_T_min   0.493
_shelx_estimated_absorpt_T_max   0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5146
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS-2014/5, Bruker AXS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26825
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.565
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3311
_reflns_number_gt                3246
_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+11.4845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3311
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 0.0000 0.20216(2) 0.2500 0.01688(10) Uani 1 2 d S T P . .
Cl1 Cl 0.06501(3) 0.04700(7) 0.19359(4) 0.02852(17) Uani 1 1 d . . . . .
F1 F 0.19875(9) 1.06747(17) 0.06937(10) 0.0359(4) Uani 1 1 d . . . . .
F2 F 0.24828(9) 0.94453(18) -0.01844(9) 0.0320(4) Uani 1 1 d . . . . .
N1 N 0.05017(10) 0.3536(2) 0.20059(11) 0.0166(4) Uani 1 1 d . . . . .
N2 N 0.23832(12) 0.8480(2) 0.10007(12) 0.0248(5) Uani 1 1 d . . . . .
N3 N 0.13481(12) 0.8808(2) 0.02185(12) 0.0237(5) Uani 1 1 d . . . . .
C1 C 0.09939(13) 0.3495(3) 0.15107(14) 0.0201(5) Uani 1 1 d . . . . .
H1 H 0.1155 0.2662 0.1347 0.024 Uiso 1 1 calc R U . . .
C2 C 0.12839(13) 0.4646(3) 0.12214(14) 0.0207(5) Uani 1 1 d . . . . .
H2 H 0.1636 0.4581 0.0868 0.025 Uiso 1 1 calc R U . . .
C3 C 0.10615(13) 0.5873(3) 0.14458(14) 0.0194(5) Uani 1 1 d . . . . .
C4 C 0.05359(13) 0.5943(3) 0.19780(14) 0.0180(5) Uani 1 1 d . . . . .
C5 C 0.02702(12) 0.4742(2) 0.22359(13) 0.0167(5) Uani 1 1 d . . . . .
C6 C 0.02590(14) 0.7156(3) 0.22554(15) 0.0227(6) Uani 1 1 d . . . . .
H6 H 0.0443 0.7972 0.2093 0.027 Uiso 1 1 calc R U . . .
C7 C 0.13757(14) 0.7089(3) 0.11315(15) 0.0203(5) Uani 1 1 d . . . . .
C8 C 0.20421(14) 0.7447(3) 0.13500(14) 0.0230(6) Uani 1 1 d . . . . .
C9 C 0.25088(15) 0.6880(3) 0.18682(16) 0.0276(6) Uani 1 1 d . . . . .
C10 C 0.31195(15) 0.7559(3) 0.17995(16) 0.0311(6) Uani 1 1 d . . . . .
H10 H 0.3530 0.7399 0.2069 0.037 Uiso 1 1 calc R U . . .
C11 C 0.30334(15) 0.8532(3) 0.12631(16) 0.0280(6) Uani 1 1 d . . . . .
C12 C 0.35583(15) 0.9487(3) 0.10057(17) 0.0346(7) Uani 1 1 d . . . . .
H12A H 0.3719 0.9222 0.0526 0.052 Uiso 1 1 calc R U . . .
H12B H 0.3950 0.9501 0.1344 0.052 Uiso 1 1 calc R U . . .
H12C H 0.3353 1.0369 0.0978 0.052 Uiso 1 1 calc R U . . .
C13 C 0.23942(17) 0.5772(4) 0.23945(18) 0.0362(7) Uani 1 1 d . . . . .
H13A H 0.2405 0.4929 0.2136 0.054 Uiso 1 1 calc R U . . .
H13B H 0.1944 0.5882 0.2626 0.054 Uiso 1 1 calc R U . . .
H13C H 0.2759 0.5785 0.2764 0.054 Uiso 1 1 calc R U . . .
C14 C 0.10256(14) 0.7760(3) 0.05796(15) 0.0219(5) Uani 1 1 d . . . . .
C15 C 0.03655(14) 0.7565(3) 0.02477(15) 0.0251(6) Uani 1 1 d . . . . .
C16 C 0.03140(15) 0.8473(3) -0.03010(16) 0.0296(6) Uani 1 1 d . . . . .
H16 H -0.0069 0.8576 -0.0619 0.035 Uiso 1 1 calc R U . . .
C17 C 0.09259(15) 0.9229(3) -0.03127(16) 0.0280(6) Uani 1 1 d . . . . .
C18 C 0.11052(17) 1.0315(3) -0.08291(18) 0.0354(7) Uani 1 1 d . . . . .
H18A H 0.1262 1.1090 -0.0557 0.053 Uiso 1 1 calc R U . . .
H18B H 0.0697 1.0547 -0.1117 0.053 Uiso 1 1 calc R U . . .
H18C H 0.1474 1.0018 -0.1151 0.053 Uiso 1 1 calc R U . . .
C19 C -0.01940(14) 0.6604(3) 0.04497(17) 0.0288(6) Uani 1 1 d . . . . .
H19A H -0.0395 0.6865 0.0913 0.043 Uiso 1 1 calc R U . . .
H19B H 0.0003 0.5717 0.0492 0.043 Uiso 1 1 calc R U . . .
H19C H -0.0554 0.6606 0.0075 0.043 Uiso 1 1 calc R U . . .
B1 B 0.20630(17) 0.9399(3) 0.04189(18) 0.0258(7) 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
Pd1 N1 2.036(2) . ?
Pd1 N1 2.036(2) 2 ?
Pd1 Cl1 2.2724(7) . ?
Pd1 Cl1 2.2725(7) 2 ?
F1 B1 1.398(4) . ?
F2 B1 1.385(4) . ?
N1 C1 1.326(3) . ?
N1 C5 1.371(3) . ?
N2 C11 1.349(4) . ?
N2 C8 1.398(4) . ?
N2 B1 1.551(4) . ?
N3 C17 1.344(4) . ?
N3 C14 1.403(3) . ?
N3 B1 1.552(4) . ?
C1 C2 1.402(4) . ?
C2 C3 1.381(4) . ?
C3 C4 1.422(4) . ?
C3 C7 1.494(4) . ?
C4 C5 1.406(4) . ?
C4 C6 1.437(4) . ?
C5 C5 1.436(5) 2 ?
C6 C6 1.355(6) 2 ?
C7 C8 1.399(4) . ?
C7 C14 1.399(4) . ?
C8 C9 1.434(4) . ?
C9 C10 1.376(4) . ?
C9 C13 1.503(4) . ?
C10 C11 1.408(5) . ?
C11 C12 1.484(4) . ?
C14 C15 1.429(4) . ?
C15 C16 1.374(4) . ?
C15 C19 1.506(4) . ?
C16 C17 1.412(4) . ?
C17 C18 1.500(4) . ?

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 82.12(12) . 2 ?
N1 Pd1 Cl1 92.80(6) . . ?
N1 Pd1 Cl1 174.31(6) 2 . ?
N1 Pd1 Cl1 174.31(6) . 2 ?
N1 Pd1 Cl1 92.80(6) 2 2 ?
Cl1 Pd1 Cl1 92.37(3) . 2 ?
C1 N1 C5 118.7(2) . . ?
C1 N1 Pd1 129.26(18) . . ?
C5 N1 Pd1 112.07(16) . . ?
C11 N2 C8 107.8(2) . . ?
C11 N2 B1 126.5(2) . . ?
C8 N2 B1 125.6(2) . . ?
C17 N3 C14 108.5(2) . . ?
C17 N3 B1 126.2(2) . . ?
C14 N3 B1 125.3(2) . . ?
N1 C1 C2 121.9(2) . . ?
C3 C2 C1 120.6(2) . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 C7 119.9(2) . . ?
C4 C3 C7 121.5(2) . . ?
C5 C4 C3 117.1(2) . . ?
C5 C4 C6 118.8(2) . . ?
C3 C4 C6 124.1(2) . . ?
N1 C5 C4 123.1(2) . . ?
N1 C5 C5 116.87(13) . 2 ?
C4 C5 C5 120.02(14) . 2 ?
C6 C6 C4 121.17(15) 2 . ?
C8 C7 C14 121.8(2) . . ?
C8 C7 C3 118.6(2) . . ?
C14 C7 C3 119.2(2) . . ?
N2 C8 C7 119.9(3) . . ?
N2 C8 C9 108.1(2) . . ?
C7 C8 C9 131.8(3) . . ?
C10 C9 C8 106.1(3) . . ?
C10 C9 C13 124.3(3) . . ?
C8 C9 C13 129.6(3) . . ?
C9 C10 C11 108.5(3) . . ?
N2 C11 C10 109.4(2) . . ?
N2 C11 C12 123.4(3) . . ?
C10 C11 C12 127.2(3) . . ?
C7 C14 N3 120.0(2) . . ?
C7 C14 C15 132.4(3) . . ?
N3 C14 C15 107.5(2) . . ?
C16 C15 C14 106.6(2) . . ?
C16 C15 C19 124.6(3) . . ?
C14 C15 C19 128.8(3) . . ?
C15 C16 C17 108.5(3) . . ?
N3 C17 C16 108.9(3) . . ?
N3 C17 C18 123.8(3) . . ?
C16 C17 C18 127.3(3) . . ?
F2 B1 F1 108.9(2) . . ?
F2 B1 N2 110.2(2) . . ?
F1 B1 N2 110.3(2) . . ?
F2 B1 N3 110.4(2) . . ?
F1 B1 N3 110.4(2) . . ?
N2 B1 N3 106.7(2) . . ?

_refine_diff_density_max         1.043
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.085



