# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_KGO-641
_database_code_depnum_ccdc_archive 'CCDC 2068310'
loop_
_audit_author_name
_audit_author_address
'Elizaveta Melnikova'
;INEOS
Russia
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C43 H34 F3 I P2 Pd'
_chemical_formula_sum            'C43 H34 F3 I P2 Pd'
_chemical_formula_weight         902.94
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   25.1867(15)
_cell_length_b                   13.4727(8)
_cell_length_c                   11.4702(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.6700(10)
_cell_angle_gamma                90
_cell_volume                     3617.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3027
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.502
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0736 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.8815.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23605
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_min         1.744
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4028
_reflns_number_total             5526
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.172
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         5526
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.025
_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)+(0.0332P)²+1.3187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0862
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
F3 \\sim F1 \\sim F2 \\sim F3 \\sim F1 \\sim F2: within 1.7A with sigma of 0.01
and sigma for terminal atoms of 0.02
Uanis(F1) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F1) = Uanis(F1)
3. Others
 Fixed Sof: F3(0.5) F2(0.5) F1(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C17(H17), C2(H2), C19(H19), C7(H7), C13(H13), C16(H16), C23(H23),
 C11(H11), C14(H14), C10(H10), C15(H15), C20(H20), C9(H9), C8(H8), C22(H22),
 C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I1 I 0.5000 0.96045(2) 0.7500 0.02304(9) Uani 1 2 d S T P . .
Pd1 Pd 0.5000 0.76059(2) 0.7500 0.01394(8) Uani 1 2 d S T P . .
P1 P 0.40001(3) 0.75594(6) 0.67756(8) 0.01443(16) Uani 1 1 d . . . . .
C18 C 0.36838(12) 0.8286(2) 0.5342(3) 0.0167(6) Uani 1 1 d . . . . .
C3 C 0.48236(12) 0.4551(2) 0.6375(3) 0.0194(7) Uani 1 1 d . . . . .
H3 H 0.4701 0.4212 0.5615 0.023 Uiso 1 1 calc R . . . .
C4 C 0.5000 0.4037(4) 0.7500 0.0215(10) Uani 1 2 d S T P . .
C12 C 0.36770(12) 0.7947(2) 0.7890(3) 0.0143(6) Uani 1 1 d . . . . .
C17 C 0.39956(13) 0.8451(2) 0.8983(3) 0.0193(7) Uani 1 1 d . . . . .
H17 H 0.4374 0.8617 0.9136 0.023 Uiso 1 1 calc R . . . .
C2 C 0.48333(12) 0.5583(2) 0.6399(3) 0.0168(6) Uani 1 1 d . . . . .
H2 H 0.4723 0.5929 0.5645 0.020 Uiso 1 1 calc R . . . .
C1 C 0.5000 0.6107(3) 0.7500 0.0167(9) Uani 1 2 d S T P . .
C19 C 0.31396(12) 0.8717(2) 0.4977(3) 0.0189(6) Uani 1 1 d . . . . .
H19 H 0.2935 0.8683 0.5506 0.023 Uiso 1 1 calc R . . . .
C6 C 0.36689(11) 0.6338(2) 0.6301(3) 0.0155(6) Uani 1 1 d . . . . .
C7 C 0.37393(12) 0.5619(2) 0.7226(3) 0.0184(7) Uani 1 1 d . . . . .
H7 H 0.3904 0.5797 0.8068 0.022 Uiso 1 1 calc R . . . .
C13 C 0.31087(13) 0.7698(2) 0.7683(3) 0.0182(6) Uani 1 1 d . . . . .
H13 H 0.2892 0.7356 0.6960 0.022 Uiso 1 1 calc R . . . .
C16 C 0.37513(15) 0.8708(2) 0.9849(3) 0.0244(7) Uani 1 1 d . . . . .
H16 H 0.3966 0.9051 1.0574 0.029 Uiso 1 1 calc R . . . .
C23 C 0.39866(14) 0.8361(3) 0.4547(3) 0.0232(7) Uani 1 1 d . . . . .
H23 H 0.4350 0.8087 0.4786 0.028 Uiso 1 1 calc R . . . .
C11 C 0.33980(12) 0.6066(3) 0.5044(3) 0.0204(7) Uani 1 1 d . . . . .
H11 H 0.3338 0.6537 0.4416 0.025 Uiso 1 1 calc R . . . .
C14 C 0.28663(14) 0.7959(2) 0.8547(3) 0.0225(7) Uani 1 1 d . . . . .
H14 H 0.2487 0.7801 0.8396 0.027 Uiso 1 1 calc R . . . .
C10 C 0.32171(13) 0.5089(3) 0.4731(3) 0.0260(8) Uani 1 1 d . . . . .
H10 H 0.3032 0.4915 0.3893 0.031 Uiso 1 1 calc R . . . .
C15 C 0.31910(15) 0.8455(2) 0.9638(3) 0.0249(7) Uani 1 1 d . . . . .
H15 H 0.3032 0.8617 1.0227 0.030 Uiso 1 1 calc R . . . .
C20 C 0.29052(13) 0.9195(2) 0.3826(3) 0.0233(7) Uani 1 1 d . . . . .
H20 H 0.2543 0.9476 0.3584 0.028 Uiso 1 1 calc R . . . .
C9 C 0.33102(14) 0.4379(3) 0.5649(4) 0.0271(8) Uani 1 1 d . . . . .
H9 H 0.3202 0.3724 0.5432 0.033 Uiso 1 1 calc R . . . .
C8 C 0.35684(13) 0.4650(3) 0.6909(3) 0.0238(7) Uani 1 1 d . . . . .
H8 H 0.3625 0.4178 0.7535 0.029 Uiso 1 1 calc R . . . .
F3 F 0.5060(4) 0.2527(5) 0.6520(9) 0.061(2) Uani 0.5 1 d . U . . .
C22 C 0.37511(14) 0.8842(3) 0.3402(3) 0.0257(8) Uani 1 1 d . . . . .
H22 H 0.3957 0.8889 0.2878 0.031 Uiso 1 1 calc R . . . .
C21 C 0.32082(14) 0.9255(3) 0.3036(3) 0.0241(7) Uani 1 1 d . . . . .
H21 H 0.3049 0.9570 0.2264 0.029 Uiso 1 1 calc R . . . .
C5 C 0.5000 0.2943(4) 0.7500 0.0385(14) Uani 1 2 d S T P . .
F2 F 0.4426(2) 0.2605(3) 0.7242(8) 0.0650(17) Uani 0.5 1 d . U . . .
F1 F 0.4753(5) 0.2530(6) 0.6494(10) 0.096(3) Uani 0.5 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
I1 Pd1 2.6927(5) . ?
Pd1 P1 2.3434(8) 2_656 ?
Pd1 P1 2.3434(8) . ?
Pd1 C1 2.019(4) . ?
P1 C18 1.824(3) . ?
P1 C12 1.827(3) . ?
P1 C6 1.835(3) . ?
C18 C19 1.403(4) . ?
C18 C23 1.392(4) . ?
C3 C4 1.385(4) . ?
C3 C2 1.391(4) . ?
C4 C3 1.385(4) 2_656 ?
C4 C5 1.474(7) . ?
C12 C17 1.391(4) . ?
C12 C13 1.402(4) . ?
C17 C16 1.392(5) . ?
C2 C1 1.370(4) . ?
C1 C2 1.370(4) 2_656 ?
C19 C20 1.390(4) . ?
C6 C7 1.399(4) . ?
C6 C11 1.396(4) . ?
C7 C8 1.381(4) . ?
C13 C14 1.388(4) . ?
C16 C15 1.384(5) . ?
C23 C22 1.386(5) . ?
C11 C10 1.397(5) . ?
C14 C15 1.388(5) . ?
C10 C9 1.378(5) . ?
C20 C21 1.385(5) . ?
C9 C8 1.397(5) . ?
F3 C5 1.314(7) . ?
F3 F2 1.532(11) 2_656 ?
F3 F1 0.763(11) . ?
C22 C21 1.390(5) . ?
C5 F3 1.314(7) 2_656 ?
C5 F2 1.439(5) . ?
C5 F2 1.439(5) 2_656 ?
C5 F1 1.225(9) 2_656 ?
C5 F1 1.225(10) . ?
F2 F3 1.532(11) 2_656 ?
F2 F1 1.395(13) . ?

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
P1 Pd1 I1 91.53(2) 2_656 . ?
P1 Pd1 I1 91.53(2) . . ?
P1 Pd1 P1 176.94(4) . 2_656 ?
C1 Pd1 I1 180.0 . . ?
C1 Pd1 P1 88.47(2) . 2_656 ?
C1 Pd1 P1 88.47(2) . . ?
C18 P1 Pd1 111.08(10) . . ?
C18 P1 C12 108.55(14) . . ?
C18 P1 C6 102.37(14) . . ?
C12 P1 Pd1 116.26(10) . . ?
C12 P1 C6 101.13(14) . . ?
C6 P1 Pd1 116.14(9) . . ?
C19 C18 P1 123.0(2) . . ?
C23 C18 P1 117.9(2) . . ?
C23 C18 C19 119.0(3) . . ?
C4 C3 C2 118.9(3) . . ?
C3 C4 C3 120.0(4) . 2_656 ?
C3 C4 C5 120.0(2) . . ?
C3 C4 C5 120.0(2) 2_656 . ?
C17 C12 P1 120.8(2) . . ?
C17 C12 C13 118.8(3) . . ?
C13 C12 P1 120.3(2) . . ?
C12 C17 C16 120.3(3) . . ?
C1 C2 C3 122.0(3) . . ?
C2 C1 Pd1 121.0(2) . . ?
C2 C1 Pd1 121.0(2) 2_656 . ?
C2 C1 C2 118.0(4) 2_656 . ?
C20 C19 C18 120.1(3) . . ?
C7 C6 P1 118.6(2) . . ?
C11 C6 P1 122.5(3) . . ?
C11 C6 C7 118.6(3) . . ?
C8 C7 C6 121.0(3) . . ?
C14 C13 C12 120.7(3) . . ?
C15 C16 C17 120.3(3) . . ?
C22 C23 C18 120.6(3) . . ?
C6 C11 C10 120.1(3) . . ?
C15 C14 C13 119.8(3) . . ?
C9 C10 C11 120.7(3) . . ?
C16 C15 C14 120.0(3) . . ?
C21 C20 C19 120.3(3) . . ?
C10 C9 C8 119.5(3) . . ?
C7 C8 C9 120.0(3) . . ?
C5 F3 F2 60.1(4) . 2_656 ?
F1 F3 C5 66.2(10) . . ?
F1 F3 F2 122.2(14) . 2_656 ?
C23 C22 C21 120.1(3) . . ?
C20 C21 C22 119.8(3) . . ?
F3 C5 C4 115.3(4) . . ?
F3 C5 C4 115.3(4) 2_656 . ?
F3 C5 F3 129.5(8) 2_656 . ?
F3 C5 F2 96.5(4) 2_656 2_656 ?
F3 C5 F2 67.5(4) 2_656 . ?
F3 C5 F2 96.5(4) . . ?
F3 C5 F2 67.5(4) . 2_656 ?
F2 C5 C4 108.5(3) . . ?
F2 C5 C4 108.5(3) 2_656 . ?
F2 C5 F2 143.0(6) . 2_656 ?
F1 C5 C4 117.1(5) 2_656 . ?
F1 C5 C4 117.1(5) . . ?
F1 C5 F3 115.7(6) . 2_656 ?
F1 C5 F3 34.8(5) 2_656 2_656 ?
F1 C5 F3 115.7(6) 2_656 . ?
F1 C5 F3 34.8(5) . . ?
F1 C5 F2 99.9(6) 2_656 . ?
F1 C5 F2 99.9(6) . 2_656 ?
F1 C5 F2 62.6(6) . . ?
F1 C5 F2 62.6(6) 2_656 2_656 ?
F1 C5 F1 125.9(10) 2_656 . ?
C5 F2 F3 52.4(3) . 2_656 ?
F1 F2 F3 94.4(5) . 2_656 ?
F1 F2 C5 51.2(4) . . ?
F3 F1 C5 79.1(11) . . ?
F3 F1 F2 142.8(16) . . ?
C5 F1 F2 66.3(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
