# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mdk052
_database_code_depnum_ccdc_archive 'CCDC 1512973'
_audit_update_record             
;
2016-10-28 deposited with the CCDC.
2017-01-19 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         'C39 H42 Br Cl2 N3 O2 P2 Pd, C7 H8'
_chemical_formula_sum            'C46 H50 Br Cl2 N3 O2 P2 Pd'
_chemical_formula_weight         996.04

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'
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'
P P 0.2955 0.4335 '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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   12.7416(3)
_cell_length_b                   15.3629(4)
_cell_length_c                   22.5851(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4420.99(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9681
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      67.20

_exptl_crystal_description       Cut
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    6.563
_shelx_estimated_absorpt_T_min   0.354
_shelx_estimated_absorpt_T_max   0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5841
_exptl_absorpt_correction_T_max  0.7691
_exptl_absorpt_process_details   
; 
(SADABS; Sheldrick, 2003) 
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed-tube microsource X-ray generator'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            28240
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.479
_diffrn_reflns_theta_max         67.195
_diffrn_reflns_theta_full        67.195
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             7828
_reflns_number_gt                7638
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.983

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0204P)²+1.7694P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
_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 3296 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.021(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7828
_refine_ls_number_parameters     588
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0511
_refine_ls_wR_factor_gt          0.0506
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.039
_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 0.85105(2) 0.18758(2) 0.14641(2) 0.01272(6) Uani 1 1 d . . . . .
Br1 Br 1.00777(3) 0.20396(2) 0.07913(2) 0.01788(8) Uani 1 1 d . . . . .
Cl1 Cl 1.29122(7) 0.16732(6) 0.44134(4) 0.02521(19) Uani 1 1 d . . . . .
Cl2 Cl 0.49795(7) 0.12378(7) 0.35103(4) 0.0328(2) Uani 1 1 d . . . . .
C1 C 1.0116(3) 0.2213(2) 0.37125(14) 0.0186(7) Uani 1 1 d . . . . .
H1A H 0.9492 0.2505 0.3829 0.022 Uiso 1 1 calc R U . . .
C2 C 1.0939(3) 0.2152(2) 0.41078(15) 0.0208(7) Uani 1 1 d . . . . .
H2A H 1.0879 0.2387 0.4496 0.025 Uiso 1 1 calc R U . . .
C3 C 1.1855(3) 0.1741(2) 0.39279(15) 0.0187(7) Uani 1 1 d . . . . .
C4 C 1.1958(3) 0.1376(2) 0.33711(15) 0.0180(7) Uani 1 1 d . . . . .
H4A H 1.2594 0.1103 0.3253 0.022 Uiso 1 1 calc R U . . .
C4A C 1.1111(3) 0.1421(2) 0.29913(14) 0.0160(7) Uani 1 1 d . . . . .
O5 O 1.12264(18) 0.10534(16) 0.24464(10) 0.0175(5) Uani 1 1 d . . . . .
C6 C 1.0276(3) 0.0873(2) 0.21271(15) 0.0162(7) Uani 1 1 d . . . . .
H6A H 1.0466 0.0820 0.1699 0.019 Uiso 1 1 calc R U . . .
N7 N 0.9498(2) 0.15723(19) 0.21775(12) 0.0151(6) Uani 1 1 d . . . . .
C7A C 0.7364(3) 0.1684(2) 0.20569(14) 0.0159(7) Uani 1 1 d . . . . .
C8 C 0.6556(3) 0.1082(2) 0.19853(15) 0.0191(7) Uani 1 1 d . . . . .
H8A H 0.6494 0.0774 0.1622 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5842(3) 0.0924(3) 0.24359(16) 0.0224(8) Uani 1 1 d . . . . .
H9A H 0.5301 0.0505 0.2387 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5932(3) 0.1389(3) 0.29588(16) 0.0218(8) Uani 1 1 d . . . . .
C11 C 0.6742(3) 0.1960(2) 0.30558(14) 0.0189(7) Uani 1 1 d . . . . .
H11A H 0.6797 0.2263 0.3421 0.023 Uiso 1 1 calc R U . . .
C11A C 0.7484(3) 0.2089(2) 0.26104(14) 0.0156(7) Uani 1 1 d . . . . .
C12 C 0.8484(3) 0.2587(2) 0.27432(14) 0.0169(7) Uani 1 1 d . . . . .
H12A H 0.8556 0.3082 0.2466 0.020 Uiso 1 1 calc R U . . .
H12B H 0.8460 0.2820 0.3152 0.020 Uiso 1 1 calc R U . . .
C12A C 0.9408(3) 0.1977(2) 0.26767(14) 0.0151(7) Uani 1 1 d . . . . .
C12B C 1.0179(3) 0.1856(2) 0.31444(14) 0.0156(6) Uani 1 1 d . . . . .
C13 C 0.9766(3) 0.0022(2) 0.23120(15) 0.0161(7) Uani 1 1 d . . . . .
C14 C 0.8964(3) -0.0307(3) 0.19577(17) 0.0236(8) Uani 1 1 d . . . . .
H14A H 0.8780 -0.0018 0.1601 0.028 Uiso 1 1 calc R U . . .
C15 C 0.8432(3) -0.1055(2) 0.21241(18) 0.0281(8) Uani 1 1 d . . . . .
H15A H 0.7886 -0.1276 0.1880 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8695(3) -0.1483(2) 0.26461(17) 0.0252(8) Uani 1 1 d . . . . .
H16A H 0.8322 -0.1991 0.2762 0.030 Uiso 1 1 calc R U . . .
C17 C 0.9499(3) -0.1167(2) 0.29948(16) 0.0228(8) Uani 1 1 d . . . . .
H17A H 0.9689 -0.1465 0.3348 0.027 Uiso 1 1 calc R U . . .
C18 C 1.0032(3) -0.0414(2) 0.28306(15) 0.0187(7) Uani 1 1 d . . . . .
H18A H 1.0580 -0.0197 0.3074 0.022 Uiso 1 1 calc R U . . .
P1L P 0.73795(6) 0.24080(5) 0.07787(4) 0.01295(16) Uani 1 1 d . . . . .
C1L C 0.7283(3) 0.3624(2) 0.08459(15) 0.0162(7) Uani 1 1 d . . . . .
C2L C 0.8342(3) 0.4054(2) 0.07236(16) 0.0206(7) Uani 1 1 d . . . . .
H2LA H 0.8889 0.3762 0.0954 0.031 Uiso 1 1 calc R U . . .
H2LB H 0.8310 0.4670 0.0837 0.031 Uiso 1 1 calc R U . . .
H2LC H 0.8506 0.4008 0.0301 0.031 Uiso 1 1 calc R U . . .
C3L C 0.6979(3) 0.3792(2) 0.14987(15) 0.0219(7) Uani 1 1 d . . . . .
H3LA H 0.7570 0.3639 0.1756 0.033 Uiso 1 1 calc R U . . .
H3LB H 0.6368 0.3436 0.1603 0.033 Uiso 1 1 calc R U . . .
H3LC H 0.6806 0.4409 0.1551 0.033 Uiso 1 1 calc R U . . .
C4L C 0.6432(3) 0.4027(2) 0.04541(15) 0.0195(7) Uani 1 1 d . . . . .
H4LA H 0.5744 0.3797 0.0569 0.029 Uiso 1 1 calc R U . . .
H4LB H 0.6571 0.3882 0.0039 0.029 Uiso 1 1 calc R U . . .
H4LC H 0.6436 0.4661 0.0503 0.029 Uiso 1 1 calc R U . . .
C5L C 0.6022(2) 0.2047(2) 0.07605(14) 0.0172(7) Uani 1 1 d . . . . .
H5LA H 0.5664 0.2235 0.1123 0.026 Uiso 1 1 calc R U . . .
H5LB H 0.6000 0.1410 0.0733 0.026 Uiso 1 1 calc R U . . .
H5LC H 0.5669 0.2300 0.0416 0.026 Uiso 1 1 calc R U . . .
P2L P 0.78600(7) 0.02643(6) 0.01583(4) 0.01523(17) Uani 1 1 d . . . . .
O1L O 0.7477(2) 0.03312(16) 0.07784(10) 0.0203(5) Uani 1 1 d . . . . .
C6L C 0.6919(3) -0.0349(2) -0.03038(16) 0.0197(7) Uani 1 1 d . . . . .
C7L C 0.7197(3) -0.0414(3) -0.09657(16) 0.0274(9) Uani 1 1 d . . . . .
H7LA H 0.7913 -0.0637 -0.1009 0.041 Uiso 1 1 calc R U . . .
H7LB H 0.7149 0.0163 -0.1148 0.041 Uiso 1 1 calc R U . . .
H7LC H 0.6705 -0.0811 -0.1162 0.041 Uiso 1 1 calc R U . . .
C8L C 0.6889(3) -0.1265(2) -0.00379(18) 0.0281(9) Uani 1 1 d . . . . .
H8LA H 0.7529 -0.1579 -0.0147 0.042 Uiso 1 1 calc R U . . .
H8LB H 0.6276 -0.1578 -0.0190 0.042 Uiso 1 1 calc R U . . .
H8LC H 0.6842 -0.1224 0.0394 0.042 Uiso 1 1 calc R U . . .
C9L C 0.5843(3) 0.0084(3) -0.02375(18) 0.0280(9) Uani 1 1 d . . . . .
H9LA H 0.5866 0.0669 -0.0410 0.042 Uiso 1 1 calc R U . . .
H9LB H 0.5662 0.0125 0.0183 0.042 Uiso 1 1 calc R U . . .
H9LC H 0.5313 -0.0265 -0.0443 0.042 Uiso 1 1 calc R U . . .
C10L C 0.9130(3) -0.0245(2) 0.01019(16) 0.0217(8) Uani 1 1 d . . . . .
H10A H 0.9296 -0.0351 -0.0316 0.033 Uiso 1 1 calc R U . . .
H10B H 0.9123 -0.0800 0.0316 0.033 Uiso 1 1 calc R U . . .
H10C H 0.9663 0.0139 0.0275 0.033 Uiso 1 1 calc R U . . .
C11L C 0.7793(2) 0.2171(2) 0.00047(13) 0.0137(6) Uani 1 1 d . . . . .
C12L C 0.8044(3) 0.1311(2) -0.02076(14) 0.0143(7) Uani 1 1 d . . . . .
N13L N 0.8436(2) 0.11888(18) -0.07468(12) 0.0168(6) Uani 1 1 d . . . . .
C14L C 0.8526(3) 0.1891(2) -0.11113(13) 0.0158(6) Uani 1 1 d . . . . .
C15L C 0.8916(3) 0.1777(3) -0.16934(15) 0.0217(8) Uani 1 1 d . . . . .
H15B H 0.9151 0.1223 -0.1823 0.026 Uiso 1 1 calc R U . . .
C16L C 0.8948(3) 0.2479(3) -0.20653(16) 0.0241(8) Uani 1 1 d . . . . .
H16B H 0.9206 0.2409 -0.2457 0.029 Uiso 1 1 calc R U . . .
C17L C 0.8604(3) 0.3302(2) -0.18763(15) 0.0239(8) Uani 1 1 d . . . . .
H17B H 0.8618 0.3777 -0.2145 0.029 Uiso 1 1 calc R U . . .
C18L C 0.8248(3) 0.3431(2) -0.13094(15) 0.0225(8) Uani 1 1 d . . . . .
H18B H 0.8026 0.3992 -0.1184 0.027 Uiso 1 1 calc R U . . .
C19L C 0.8215(2) 0.2720(2) -0.09152(14) 0.0164(7) Uani 1 1 d . . . . .
N20L N 0.7875(2) 0.28511(18) -0.03451(12) 0.0159(6) Uani 1 1 d . . . . .
C1T C 1.2323(7) 0.0780(6) 0.6214(5) 0.028(2) Uani 0.557(9) 1 d D U P A 1
C2T C 1.1530(10) 0.1053(9) 0.5834(6) 0.029(3) Uani 0.557(9) 1 d D U P A 1
H2TA H 1.1682 0.1144 0.5427 0.035 Uiso 0.557(9) 1 calc R U P A 1
C3T C 1.0519(8) 0.1195(7) 0.6041(4) 0.043(2) Uani 0.557(9) 1 d D U P A 1
H3TA H 0.9985 0.1383 0.5777 0.051 Uiso 0.557(9) 1 calc R U P A 1
C4T C 1.0290(8) 0.1061(7) 0.6634(4) 0.037(3) Uani 0.557(9) 1 d D U P A 1
H4TA H 0.9594 0.1142 0.6774 0.045 Uiso 0.557(9) 1 calc R U P A 1
C5T C 1.1073(12) 0.0811(18) 0.7023(6) 0.024(3) Uani 0.557(9) 1 d D U P A 1
H5TA H 1.0919 0.0746 0.7432 0.028 Uiso 0.557(9) 1 calc R U P A 1
C6T C 1.2074(13) 0.0655(17) 0.6818(6) 0.026(4) Uani 0.557(9) 1 d D U P A 1
H6TA H 1.2602 0.0463 0.7085 0.032 Uiso 0.557(9) 1 calc R U P A 1
C7T C 1.3408(6) 0.0601(5) 0.5982(3) 0.031(2) Uani 0.557(9) 1 d D U P A 1
H7TA H 1.3928 0.0772 0.6280 0.046 Uiso 0.557(9) 1 calc R U P A 1
H7TB H 1.3523 0.0935 0.5618 0.046 Uiso 0.557(9) 1 calc R U P A 1
H7TC H 1.3481 -0.0022 0.5897 0.046 Uiso 0.557(9) 1 calc R U P A 1
C1T' C 1.0680(9) 0.0934(7) 0.6437(6) 0.031(3) Uani 0.443(9) 1 d D U P A 2
C2T' C 1.1317(16) 0.074(2) 0.6914(7) 0.028(5) Uani 0.443(9) 1 d D U P A 2
H2TB H 1.1003 0.0724 0.7295 0.033 Uiso 0.443(9) 1 calc R U P A 2
C3T' C 1.2368(16) 0.056(2) 0.6874(9) 0.033(5) Uani 0.443(9) 1 d D U P A 2
H3TB H 1.2765 0.0443 0.7221 0.040 Uiso 0.443(9) 1 calc R U P A 2
C4T' C 1.2841(13) 0.0566(7) 0.6332(5) 0.040(3) Uani 0.443(9) 1 d D U P A 2
H4TB H 1.3568 0.0439 0.6295 0.048 Uiso 0.443(9) 1 calc R U P A 2
C5T' C 1.2250(12) 0.0753(7) 0.5841(6) 0.044(3) Uani 0.443(9) 1 d D U P A 2
H5TB H 1.2570 0.0766 0.5461 0.052 Uiso 0.443(9) 1 calc R U P A 2
C6T' C 1.1194(14) 0.0921(14) 0.5899(10) 0.045(6) Uani 0.443(9) 1 d D U P A 2
H6TB H 1.0799 0.1034 0.5551 0.054 Uiso 0.443(9) 1 calc R U P A 2
C7T' C 0.9526(9) 0.1150(7) 0.6494(5) 0.046(3) Uani 0.443(9) 1 d D U P A 2
H7TD H 0.9119 0.0776 0.6228 0.069 Uiso 0.443(9) 1 calc R U P A 2
H7TE H 0.9413 0.1762 0.6388 0.069 Uiso 0.443(9) 1 calc R U P A 2
H7TF H 0.9300 0.1053 0.6904 0.069 Uiso 0.443(9) 1 calc R 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
Pd1 C7A 2.004(3) . ?
Pd1 N7 2.097(3) . ?
Pd1 P1L 2.2674(8) . ?
Pd1 Br1 2.5218(4) . ?
Cl1 C3 1.740(3) . ?
Cl2 C10 1.754(4) . ?
C1 C2 1.380(5) . ?
C1 C12B 1.398(5) . ?
C2 C3 1.388(5) . ?
C3 C4 1.383(5) . ?
C4 C4A 1.381(5) . ?
C4A O5 1.362(4) . ?
C4A C12B 1.406(5) . ?
O5 C6 1.436(4) . ?
C6 N7 1.466(4) . ?
C6 C13 1.519(5) . ?
N7 C12A 1.292(4) . ?
C7A C8 1.393(5) . ?
C7A C11A 1.405(5) . ?
C8 C9 1.386(5) . ?
C9 C10 1.384(6) . ?
C10 C11 1.373(5) . ?
C11 C11A 1.394(5) . ?
C11A C12 1.515(5) . ?
C12 C12A 1.513(4) . ?
C12A C12B 1.454(4) . ?
C13 C18 1.392(5) . ?
C13 C14 1.394(5) . ?
C14 C15 1.385(6) . ?
C15 C16 1.391(6) . ?
C16 C17 1.381(5) . ?
C17 C18 1.391(5) . ?
P1L C5L 1.818(3) . ?
P1L C11L 1.862(3) . ?
P1L C1L 1.878(3) . ?
C1L C2L 1.529(5) . ?
C1L C4L 1.530(5) . ?
C1L C3L 1.546(5) . ?
P2L O1L 1.487(2) . ?
P2L C10L 1.802(4) . ?
P2L C12L 1.824(3) . ?
P2L C6L 1.848(4) . ?
C6L C9L 1.530(5) . ?
C6L C8L 1.531(5) . ?
C6L C7L 1.540(5) . ?
C11L N20L 1.314(4) . ?
C11L C12L 1.441(5) . ?
C12L N13L 1.329(4) . ?
N13L C14L 1.363(4) . ?
C14L C19L 1.405(5) . ?
C14L C15L 1.416(5) . ?
C15L C16L 1.367(5) . ?
C16L C17L 1.404(5) . ?
C17L C18L 1.373(5) . ?
C18L C19L 1.410(5) . ?
C19L N20L 1.373(4) . ?
C1T C2T 1.390(12) . ?
C1T C6T 1.414(15) . ?
C1T C7T 1.504(9) . ?
C2T C3T 1.387(11) . ?
C3T C4T 1.386(10) . ?
C4T C5T 1.383(11) . ?
C5T C6T 1.378(11) . ?
C1T' C6T' 1.38(2) . ?
C1T' C2T' 1.381(12) . ?
C1T' C7T' 1.512(11) . ?
C2T' C3T' 1.370(12) . ?
C3T' C4T' 1.365(13) . ?
C4T' C5T' 1.370(11) . ?
C5T' C6T' 1.376(12) . ?

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
C7A Pd1 N7 83.77(12) . . ?
C7A Pd1 P1L 92.62(10) . . ?
N7 Pd1 P1L 170.45(8) . . ?
C7A Pd1 Br1 174.14(9) . . ?
N7 Pd1 Br1 90.57(8) . . ?
P1L Pd1 Br1 93.21(2) . . ?
C2 C1 C12B 121.5(3) . . ?
C1 C2 C3 118.7(3) . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 Cl1 118.4(3) . . ?
C2 C3 Cl1 119.6(3) . . ?
C4A C4 C3 118.1(3) . . ?
O5 C4A C4 117.1(3) . . ?
O5 C4A C12B 120.7(3) . . ?
C4 C4A C12B 122.1(3) . . ?
C4A O5 C6 116.3(3) . . ?
O5 C6 N7 113.0(3) . . ?
O5 C6 C13 112.9(3) . . ?
N7 C6 C13 108.6(3) . . ?
C12A N7 C6 118.7(3) . . ?
C12A N7 Pd1 120.7(2) . . ?
C6 N7 Pd1 120.6(2) . . ?
C8 C7A C11A 118.6(3) . . ?
C8 C7A Pd1 124.0(2) . . ?
C11A C7A Pd1 116.7(2) . . ?
C9 C8 C7A 121.0(3) . . ?
C10 C9 C8 118.9(3) . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 Cl2 119.4(3) . . ?
C9 C10 Cl2 118.7(3) . . ?
C10 C11 C11A 119.1(3) . . ?
C11 C11A C7A 120.3(3) . . ?
C11 C11A C12 119.9(3) . . ?
C7A C11A C12 119.4(3) . . ?
C12A C12 C11A 108.8(3) . . ?
N7 C12A C12B 120.8(3) . . ?
N7 C12A C12 117.0(3) . . ?
C12B C12A C12 122.2(3) . . ?
C1 C12B C4A 117.5(3) . . ?
C1 C12B C12A 125.3(3) . . ?
C4A C12B C12A 116.9(3) . . ?
C18 C13 C14 119.1(3) . . ?
C18 C13 C6 122.9(3) . . ?
C14 C13 C6 118.0(3) . . ?
C15 C14 C13 120.3(4) . . ?
C14 C15 C16 120.3(4) . . ?
C17 C16 C15 119.7(4) . . ?
C16 C17 C18 120.2(4) . . ?
C17 C18 C13 120.4(3) . . ?
C5L P1L C11L 100.86(15) . . ?
C5L P1L C1L 104.07(16) . . ?
C11L P1L C1L 106.80(15) . . ?
C5L P1L Pd1 120.68(11) . . ?
C11L P1L Pd1 112.99(10) . . ?
C1L P1L Pd1 110.20(11) . . ?
C2L C1L C4L 110.2(3) . . ?
C2L C1L C3L 108.7(3) . . ?
C4L C1L C3L 107.8(3) . . ?
C2L C1L P1L 111.0(2) . . ?
C4L C1L P1L 113.8(2) . . ?
C3L C1L P1L 105.1(2) . . ?
O1L P2L C10L 113.05(16) . . ?
O1L P2L C12L 114.09(15) . . ?
C10L P2L C12L 103.61(17) . . ?
O1L P2L C6L 110.75(16) . . ?
C10L P2L C6L 108.77(17) . . ?
C12L P2L C6L 106.08(16) . . ?
C9L C6L C8L 109.8(3) . . ?
C9L C6L C7L 109.2(3) . . ?
C8L C6L C7L 109.0(3) . . ?
C9L C6L P2L 107.7(2) . . ?
C8L C6L P2L 105.3(2) . . ?
C7L C6L P2L 115.6(3) . . ?
N20L C11L C12L 120.7(3) . . ?
N20L C11L P1L 115.6(2) . . ?
C12L C11L P1L 123.7(2) . . ?
N13L C12L C11L 121.2(3) . . ?
N13L C12L P2L 109.8(2) . . ?
C11L C12L P2L 129.0(2) . . ?
C12L N13L C14L 118.2(3) . . ?
N13L C14L C19L 120.2(3) . . ?
N13L C14L C15L 119.5(3) . . ?
C19L C14L C15L 120.3(3) . . ?
C16L C15L C14L 118.9(4) . . ?
C15L C16L C17L 120.9(3) . . ?
C18L C17L C16L 121.1(3) . . ?
C17L C18L C19L 119.1(3) . . ?
N20L C19L C14L 121.2(3) . . ?
N20L C19L C18L 119.2(3) . . ?
C14L C19L C18L 119.6(3) . . ?
C11L N20L C19L 118.2(3) . . ?
C2T C1T C6T 118.3(10) . . ?
C2T C1T C7T 120.6(10) . . ?
C6T C1T C7T 121.1(11) . . ?
C3T C2T C1T 120.9(11) . . ?
C4T C3T C2T 119.9(10) . . ?
C5T C4T C3T 120.1(11) . . ?
C6T C5T C4T 120.2(13) . . ?
C5T C6T C1T 120.5(13) . . ?
C6T' C1T' C2T' 113.8(14) . . ?
C6T' C1T' C7T' 122.7(13) . . ?
C2T' C1T' C7T' 123.5(15) . . ?
C3T' C2T' C1T' 124.5(18) . . ?
C4T' C3T' C2T' 119.3(19) . . ?
C3T' C4T' C5T' 119.0(16) . . ?
C4T' C5T' C6T' 119.9(18) . . ?
C5T' C6T' C1T' 123.4(18) . . ?

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
C12B C1 C2 C3 1.4(5) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C1 C2 C3 Cl1 178.8(3) . . . . ?
C2 C3 C4 C4A -0.7(5) . . . . ?
Cl1 C3 C4 C4A 179.0(3) . . . . ?
C3 C4 C4A O5 -179.6(3) . . . . ?
C3 C4 C4A C12B 3.0(5) . . . . ?
C4 C4A O5 C6 162.2(3) . . . . ?
C12B C4A O5 C6 -20.4(5) . . . . ?
C4A O5 C6 N7 41.4(4) . . . . ?
C4A O5 C6 C13 -82.4(3) . . . . ?
O5 C6 N7 C12A -37.2(4) . . . . ?
C13 C6 N7 C12A 88.8(4) . . . . ?
O5 C6 N7 Pd1 145.2(2) . . . . ?
C13 C6 N7 Pd1 -88.8(3) . . . . ?
C11A C7A C8 C9 4.1(5) . . . . ?
Pd1 C7A C8 C9 174.0(3) . . . . ?
C7A C8 C9 C10 1.1(5) . . . . ?
C8 C9 C10 C11 -4.0(6) . . . . ?
C8 C9 C10 Cl2 176.1(3) . . . . ?
C9 C10 C11 C11A 1.3(6) . . . . ?
Cl2 C10 C11 C11A -178.7(3) . . . . ?
C10 C11 C11A C7A 4.1(5) . . . . ?
C10 C11 C11A C12 -169.1(3) . . . . ?
C8 C7A C11A C11 -6.8(5) . . . . ?
Pd1 C7A C11A C11 -177.4(3) . . . . ?
C8 C7A C11A C12 166.5(3) . . . . ?
Pd1 C7A C11A C12 -4.1(4) . . . . ?
C11 C11A C12 C12A 115.3(3) . . . . ?
C7A C11A C12 C12A -58.0(4) . . . . ?
C6 N7 C12A C12B 10.9(5) . . . . ?
Pd1 N7 C12A C12B -171.4(2) . . . . ?
C6 N7 C12A C12 -170.2(3) . . . . ?
Pd1 N7 C12A C12 7.4(4) . . . . ?
C11A C12 C12A N7 54.7(4) . . . . ?
C11A C12 C12A C12B -126.4(3) . . . . ?
C2 C1 C12B C4A 0.8(5) . . . . ?
C2 C1 C12B C12A -172.3(3) . . . . ?
O5 C4A C12B C1 179.7(3) . . . . ?
C4 C4A C12B C1 -3.0(5) . . . . ?
O5 C4A C12B C12A -6.7(5) . . . . ?
C4 C4A C12B C12A 170.6(3) . . . . ?
N7 C12A C12B C1 -175.3(3) . . . . ?
C12 C12A C12B C1 5.9(5) . . . . ?
N7 C12A C12B C4A 11.7(5) . . . . ?
C12 C12A C12B C4A -167.1(3) . . . . ?
O5 C6 C13 C18 15.6(4) . . . . ?
N7 C6 C13 C18 -110.5(4) . . . . ?
O5 C6 C13 C14 -167.6(3) . . . . ?
N7 C6 C13 C14 66.4(4) . . . . ?
C18 C13 C14 C15 0.6(5) . . . . ?
C6 C13 C14 C15 -176.3(3) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C17 -0.9(6) . . . . ?
C15 C16 C17 C18 1.2(5) . . . . ?
C16 C17 C18 C13 -0.6(5) . . . . ?
C14 C13 C18 C17 -0.3(5) . . . . ?
C6 C13 C18 C17 176.5(3) . . . . ?
C5L P1L C1L C2L -166.8(2) . . . . ?
C11L P1L C1L C2L -60.6(3) . . . . ?
Pd1 P1L C1L C2L 62.4(3) . . . . ?
C5L P1L C1L C4L -41.9(3) . . . . ?
C11L P1L C1L C4L 64.3(3) . . . . ?
Pd1 P1L C1L C4L -172.6(2) . . . . ?
C5L P1L C1L C3L 75.9(3) . . . . ?
C11L P1L C1L C3L -178.0(2) . . . . ?
Pd1 P1L C1L C3L -54.9(2) . . . . ?
O1L P2L C6L C9L 54.0(3) . . . . ?
C10L P2L C6L C9L 178.8(3) . . . . ?
C12L P2L C6L C9L -70.3(3) . . . . ?
O1L P2L C6L C8L -63.1(3) . . . . ?
C10L P2L C6L C8L 61.7(3) . . . . ?
C12L P2L C6L C8L 172.6(2) . . . . ?
O1L P2L C6L C7L 176.4(3) . . . . ?
C10L P2L C6L C7L -58.7(3) . . . . ?
C12L P2L C6L C7L 52.2(3) . . . . ?
C5L P1L C11L N20L 104.6(3) . . . . ?
C1L P1L C11L N20L -3.8(3) . . . . ?
Pd1 P1L C11L N20L -125.1(2) . . . . ?
C5L P1L C11L C12L -77.2(3) . . . . ?
C1L P1L C11L C12L 174.3(3) . . . . ?
Pd1 P1L C11L C12L 53.0(3) . . . . ?
N20L C11L C12L N13L 4.9(5) . . . . ?
P1L C11L C12L N13L -173.2(2) . . . . ?
N20L C11L C12L P2L -172.6(3) . . . . ?
P1L C11L C12L P2L 9.4(5) . . . . ?
O1L P2L C12L N13L 176.9(2) . . . . ?
C10L P2L C12L N13L 53.6(3) . . . . ?
C6L P2L C12L N13L -60.9(3) . . . . ?
O1L P2L C12L C11L -5.4(4) . . . . ?
C10L P2L C12L C11L -128.7(3) . . . . ?
C6L P2L C12L C11L 116.8(3) . . . . ?
C11L C12L N13L C14L -4.5(5) . . . . ?
P2L C12L N13L C14L 173.4(2) . . . . ?
C12L N13L C14L C19L 0.3(5) . . . . ?
C12L N13L C14L C15L -178.4(3) . . . . ?
N13L C14L C15L C16L 176.4(3) . . . . ?
C19L C14L C15L C16L -2.3(5) . . . . ?
C14L C15L C16L C17L 0.2(5) . . . . ?
C15L C16L C17L C18L 1.5(6) . . . . ?
C16L C17L C18L C19L -0.9(6) . . . . ?
N13L C14L C19L N20L 4.0(5) . . . . ?
C15L C14L C19L N20L -177.3(3) . . . . ?
N13L C14L C19L C18L -175.8(3) . . . . ?
C15L C14L C19L C18L 2.9(5) . . . . ?
C17L C18L C19L N20L 178.9(3) . . . . ?
C17L C18L C19L C14L -1.2(5) . . . . ?
C12L C11L N20L C19L -0.6(5) . . . . ?
P1L C11L N20L C19L 177.6(2) . . . . ?
C14L C19L N20L C11L -3.7(5) . . . . ?
C18L C19L N20L C11L 176.1(3) . . . . ?
C6T C1T C2T C3T 0(2) . . . . ?
C7T C1T C2T C3T 178.1(10) . . . . ?
C1T C2T C3T C4T -0.2(18) . . . . ?
C2T C3T C4T C5T 2(2) . . . . ?
C3T C4T C5T C6T -3(3) . . . . ?
C4T C5T C6T C1T 2(3) . . . . ?
C2T C1T C6T C5T -1(3) . . . . ?
C7T C1T C6T C5T -179.1(17) . . . . ?
C6T' C1T' C2T' C3T' 1(4) . . . . ?
C7T' C1T' C2T' C3T' -178(2) . . . . ?
C1T' C2T' C3T' C4T' -1(5) . . . . ?
C2T' C3T' C4T' C5T' 1(4) . . . . ?
C3T' C4T' C5T' C6T' -1(3) . . . . ?
C4T' C5T' C6T' C1T' 2(3) . . . . ?
C2T' C1T' C6T' C5T' -2(3) . . . . ?
C7T' C1T' C6T' C5T' 177.9(14) . . . . ?

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_mdk104
_database_code_depnum_ccdc_archive 'CCDC 1512974'
_audit_update_record             
;
2016-10-28 deposited with the CCDC.
2017-01-19 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         'C18 H28 Br2 N2 P2 Pd'
_chemical_formula_sum            'C18 H28 Br2 N2 P2 Pd'
_chemical_formula_weight         600.58

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.6802(4)
_cell_length_b                   15.4523(7)
_cell_length_c                   18.3830(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2181.63(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9768
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      66.61

_exptl_crystal_description       small
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    12.567
_shelx_estimated_absorpt_T_min   0.572
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_process_details   
; 
(SADABS; Sheldrick, 2003) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed-tube microsource X-ray generator'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13372
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.737
_diffrn_reflns_theta_max         66.603
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3816
_reflns_number_gt                3690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.986

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+3.8632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
_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 1529 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.013(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3816
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.09873(5) 0.46015(2) 0.15997(2) 0.01388(10) Uani 1 1 d . . . . .
Br1 Br -0.05343(8) 0.60218(3) 0.15981(3) 0.02031(14) Uani 1 1 d . . . . .
Br2 Br 0.01799(9) 0.42773(4) 0.03165(3) 0.02366(15) Uani 1 1 d . . . . .
P1 P 0.14586(19) 0.47691(8) 0.27906(8) 0.0127(3) Uani 1 1 d . . . . .
P2 P 0.27372(18) 0.34319(8) 0.16412(8) 0.0139(3) Uani 1 1 d . . . . .
N1 N 0.3729(6) 0.4008(3) 0.3738(2) 0.0149(10) Uani 1 1 d . . . . .
C2 C 0.3101(7) 0.3985(3) 0.3073(3) 0.0125(11) Uani 1 1 d . . . . .
C3 C 0.3449(8) 0.3295(4) 0.2587(3) 0.0160(12) Uani 1 1 d . . . . .
N4 N 0.4277(6) 0.2587(3) 0.2790(2) 0.0140(9) Uani 1 1 d . . . . .
C4A C 0.4902(7) 0.2579(3) 0.3489(3) 0.0143(11) Uani 1 1 d . . . . .
C5 C 0.5805(8) 0.1848(3) 0.3751(3) 0.0176(11) Uani 1 1 d . . . . .
H5A H 0.5906 0.1345 0.3458 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6533(8) 0.1868(4) 0.4426(3) 0.0185(12) Uani 1 1 d . . . . .
H6A H 0.7149 0.1375 0.4598 0.022 Uiso 1 1 calc R U . . .
C7 C 0.6391(8) 0.2611(4) 0.4880(3) 0.0210(13) Uani 1 1 d . . . . .
H7A H 0.6926 0.2614 0.5346 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5489(7) 0.3320(3) 0.4647(3) 0.0158(11) Uani 1 1 d . . . . .
H8A H 0.5387 0.3814 0.4952 0.019 Uiso 1 1 calc R U . . .
C8A C 0.4706(7) 0.3317(3) 0.3952(3) 0.0138(11) Uani 1 1 d . . . . .
C9 C -0.0465(7) 0.4445(3) 0.3358(3) 0.0160(11) Uani 1 1 d . . . . .
C10 C -0.0668(8) 0.3457(3) 0.3288(3) 0.0222(13) Uani 1 1 d . . . . .
H10A H 0.0314 0.3170 0.3528 0.033 Uiso 1 1 calc R U . . .
H10B H -0.0689 0.3297 0.2772 0.033 Uiso 1 1 calc R U . . .
H10C H -0.1758 0.3276 0.3519 0.033 Uiso 1 1 calc R U . . .
C11 C -0.2117(8) 0.4888(4) 0.3091(3) 0.0201(12) Uani 1 1 d . . . . .
H11A H -0.2458 0.4643 0.2620 0.030 Uiso 1 1 calc R U . . .
H11B H -0.1901 0.5510 0.3036 0.030 Uiso 1 1 calc R U . . .
H11C H -0.3054 0.4797 0.3444 0.030 Uiso 1 1 calc R U . . .
C12 C -0.0148(9) 0.4695(4) 0.4154(3) 0.0246(13) Uani 1 1 d . . . . .
H12A H 0.0950 0.4440 0.4321 0.037 Uiso 1 1 calc R U . . .
H12B H -0.1107 0.4478 0.4455 0.037 Uiso 1 1 calc R U . . .
H12C H -0.0085 0.5326 0.4196 0.037 Uiso 1 1 calc R U . . .
C13 C 0.2289(8) 0.5787(3) 0.3127(3) 0.0198(12) Uani 1 1 d . . . . .
H13A H 0.1359 0.6221 0.3120 0.030 Uiso 1 1 calc R U . . .
H13B H 0.3252 0.5981 0.2818 0.030 Uiso 1 1 calc R U . . .
H13C H 0.2708 0.5712 0.3627 0.030 Uiso 1 1 calc R U . . .
C14 C 0.4790(8) 0.3582(3) 0.1107(3) 0.0175(12) Uani 1 1 d . . . . .
C15 C 0.6285(9) 0.3032(4) 0.1415(3) 0.0281(15) Uani 1 1 d . . . . .
H15A H 0.5954 0.2420 0.1406 0.042 Uiso 1 1 calc R U . . .
H15B H 0.6525 0.3209 0.1917 0.042 Uiso 1 1 calc R U . . .
H15C H 0.7332 0.3117 0.1118 0.042 Uiso 1 1 calc R U . . .
C16 C 0.5275(8) 0.4541(4) 0.1133(3) 0.0231(12) Uani 1 1 d . . . . .
H16A H 0.4341 0.4884 0.0912 0.035 Uiso 1 1 calc R U . . .
H16B H 0.6360 0.4633 0.0863 0.035 Uiso 1 1 calc R U . . .
H16C H 0.5435 0.4719 0.1640 0.035 Uiso 1 1 calc R U . . .
C17 C 0.4485(10) 0.3306(4) 0.0313(3) 0.0280(15) Uani 1 1 d . . . . .
H17A H 0.4296 0.2680 0.0292 0.042 Uiso 1 1 calc R U . . .
H17B H 0.5506 0.3458 0.0020 0.042 Uiso 1 1 calc R U . . .
H17C H 0.3457 0.3606 0.0122 0.042 Uiso 1 1 calc R U . . .
C18 C 0.1840(9) 0.2383(4) 0.1414(3) 0.0252(14) Uani 1 1 d . . . . .
H18A H 0.1189 0.2425 0.0957 0.038 Uiso 1 1 calc R U . . .
H18B H 0.1057 0.2193 0.1803 0.038 Uiso 1 1 calc R U . . .
H18C H 0.2788 0.1964 0.1358 0.038 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 P1 2.2341(15) . ?
Pd1 P2 2.2534(13) . ?
Pd1 Br1 2.4865(6) . ?
Pd1 Br2 2.4898(7) . ?
P1 C13 1.807(6) . ?
P1 C2 1.824(6) . ?
P1 C9 1.877(6) . ?
P2 C18 1.810(6) . ?
P2 C3 1.835(6) . ?
P2 C14 1.872(6) . ?
N1 C2 1.315(7) . ?
N1 C8A 1.364(7) . ?
C2 C3 1.417(8) . ?
C3 N4 1.320(8) . ?
N4 C4A 1.371(7) . ?
C4A C5 1.410(8) . ?
C4A C8A 1.431(7) . ?
C5 C6 1.362(8) . ?
C5 H5A 0.9500 . ?
C6 C7 1.424(9) . ?
C6 H6A 0.9500 . ?
C7 C8 1.365(8) . ?
C7 H7A 0.9500 . ?
C8 C8A 1.412(8) . ?
C8 H8A 0.9500 . ?
C9 C11 1.523(8) . ?
C9 C12 1.533(8) . ?
C9 C10 1.539(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C16 1.529(8) . ?
C14 C15 1.537(8) . ?
C14 C17 1.538(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 P2 87.89(5) . . ?
P1 Pd1 Br1 88.56(4) . . ?
P2 Pd1 Br1 171.20(4) . . ?
P1 Pd1 Br2 172.77(4) . . ?
P2 Pd1 Br2 91.11(4) . . ?
Br1 Pd1 Br2 93.41(2) . . ?
C13 P1 C2 103.7(3) . . ?
C13 P1 C9 108.7(3) . . ?
C2 P1 C9 102.0(2) . . ?
C13 P1 Pd1 119.6(2) . . ?
C2 P1 Pd1 108.30(18) . . ?
C9 P1 Pd1 112.72(19) . . ?
C18 P2 C3 103.3(3) . . ?
C18 P2 C14 108.1(3) . . ?
C3 P2 C14 105.1(3) . . ?
C18 P2 Pd1 118.9(2) . . ?
C3 P2 Pd1 107.6(2) . . ?
C14 P2 Pd1 112.67(17) . . ?
C2 N1 C8A 116.7(5) . . ?
N1 C2 C3 122.5(5) . . ?
N1 C2 P1 120.1(4) . . ?
C3 C2 P1 116.8(4) . . ?
N4 C3 C2 122.5(5) . . ?
N4 C3 P2 120.5(4) . . ?
C2 C3 P2 117.0(4) . . ?
C3 N4 C4A 116.2(4) . . ?
N4 C4A C5 120.0(5) . . ?
N4 C4A C8A 120.9(5) . . ?
C5 C4A C8A 119.1(5) . . ?
C6 C5 C4A 119.7(5) . . ?
C6 C5 H5A 120.1 . . ?
C4A C5 H5A 120.1 . . ?
C5 C6 C7 121.3(5) . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
C8 C7 C6 120.2(5) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C8A 119.8(5) . . ?
C7 C8 H8A 120.1 . . ?
C8A C8 H8A 120.1 . . ?
N1 C8A C8 119.5(5) . . ?
N1 C8A C4A 120.7(5) . . ?
C8 C8A C4A 119.8(5) . . ?
C11 C9 C12 109.1(5) . . ?
C11 C9 C10 109.5(5) . . ?
C12 C9 C10 110.2(5) . . ?
C11 C9 P1 110.9(4) . . ?
C12 C9 P1 109.8(4) . . ?
C10 C9 P1 107.3(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
P1 C13 H13A 109.5 . . ?
P1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
P1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C14 C15 110.0(5) . . ?
C16 C14 C17 109.6(5) . . ?
C15 C14 C17 108.1(5) . . ?
C16 C14 P2 108.0(4) . . ?
C15 C14 P2 111.6(4) . . ?
C17 C14 P2 109.6(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
P2 C18 H18A 109.5 . . ?
P2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
P2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C8A N1 C2 C3 -1.8(8) . . . . ?
C8A N1 C2 P1 168.6(4) . . . . ?
C13 P1 C2 N1 45.5(5) . . . . ?
C9 P1 C2 N1 -67.4(5) . . . . ?
Pd1 P1 C2 N1 173.5(4) . . . . ?
C13 P1 C2 C3 -143.6(4) . . . . ?
C9 P1 C2 C3 103.5(4) . . . . ?
Pd1 P1 C2 C3 -15.6(5) . . . . ?
N1 C2 C3 N4 7.1(9) . . . . ?
P1 C2 C3 N4 -163.6(4) . . . . ?
N1 C2 C3 P2 -171.6(4) . . . . ?
P1 C2 C3 P2 17.7(6) . . . . ?
C18 P2 C3 N4 43.4(5) . . . . ?
C14 P2 C3 N4 -69.8(5) . . . . ?
Pd1 P2 C3 N4 169.9(4) . . . . ?
C18 P2 C3 C2 -137.9(5) . . . . ?
C14 P2 C3 C2 108.9(5) . . . . ?
Pd1 P2 C3 C2 -11.4(5) . . . . ?
C2 C3 N4 C4A -4.6(8) . . . . ?
P2 C3 N4 C4A 174.0(4) . . . . ?
C3 N4 C4A C5 -179.9(5) . . . . ?
C3 N4 C4A C8A -2.2(8) . . . . ?
N4 C4A C5 C6 175.2(5) . . . . ?
C8A C4A C5 C6 -2.5(8) . . . . ?
C4A C5 C6 C7 0.5(9) . . . . ?
C5 C6 C7 C8 1.1(9) . . . . ?
C6 C7 C8 C8A -0.5(9) . . . . ?
C2 N1 C8A C8 177.0(5) . . . . ?
C2 N1 C8A C4A -5.0(8) . . . . ?
C7 C8 C8A N1 176.5(5) . . . . ?
C7 C8 C8A C4A -1.6(8) . . . . ?
N4 C4A C8A N1 7.3(8) . . . . ?
C5 C4A C8A N1 -175.0(5) . . . . ?
N4 C4A C8A C8 -174.6(5) . . . . ?
C5 C4A C8A C8 3.1(8) . . . . ?
C13 P1 C9 C11 83.5(4) . . . . ?
C2 P1 C9 C11 -167.4(4) . . . . ?
Pd1 P1 C9 C11 -51.5(4) . . . . ?
C13 P1 C9 C12 -37.1(5) . . . . ?
C2 P1 C9 C12 72.0(4) . . . . ?
Pd1 P1 C9 C12 -172.1(3) . . . . ?
C13 P1 C9 C10 -157.0(4) . . . . ?
C2 P1 C9 C10 -47.9(4) . . . . ?
Pd1 P1 C9 C10 68.1(4) . . . . ?
C18 P2 C14 C16 164.7(4) . . . . ?
C3 P2 C14 C16 -85.6(4) . . . . ?
Pd1 P2 C14 C16 31.3(5) . . . . ?
C18 P2 C14 C15 -74.3(5) . . . . ?
C3 P2 C14 C15 35.4(5) . . . . ?
Pd1 P2 C14 C15 152.3(4) . . . . ?
C18 P2 C14 C17 45.4(5) . . . . ?
C3 P2 C14 C17 155.2(4) . . . . ?
Pd1 P2 C14 C17 -88.0(4) . . . . ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.081


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and toluene '
####################################################################### 
# 
# 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_mdk105
_database_code_depnum_ccdc_archive 'CCDC 1512975'
_audit_update_record             
;
2016-10-28 deposited with the CCDC.
2017-01-19 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         'C25 H32 Br N3 O P2 Pd'
_chemical_formula_sum            'C25 H32 Br N3 O P2 Pd'
_chemical_formula_weight         638.78

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'
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'
P P 0.2955 0.4335 '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'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   23.4340(11)
_cell_length_b                   10.7208(5)
_cell_length_c                   10.6091(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.3448(14)
_cell_angle_gamma                90
_cell_volume                     2653.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9798
_cell_measurement_theta_min      3.79
_cell_measurement_theta_max      66.55

_exptl_crystal_description       Rod
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    8.720
_shelx_estimated_absorpt_T_min   0.180
_shelx_estimated_absorpt_T_max   0.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.289
_exptl_absorpt_correction_T_max  0.418

_exptl_absorpt_process_details   
; 
(SADABS; Sheldrick, 2003) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed-tube microsource X-ray generator'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23472
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.789
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_full        66.577
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4648
_reflns_number_gt                4584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.989

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0292P)²+4.0320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
_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 2111 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.016(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4648
_refine_ls_number_parameters     306
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0562
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.075
_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 0.76876(2) 0.66131(3) 0.70544(3) 0.01255(9) Uani 1 1 d . . . . .
Br1 Br 0.70392(2) 0.84065(4) 0.73323(4) 0.01726(12) Uani 1 1 d . . . . .
P1L P 0.82694(5) 0.49590(10) 0.69564(10) 0.0124(2) Uani 1 1 d . . . . .
C1L C 0.8930(2) 0.5179(5) 0.6094(4) 0.0180(10) Uani 1 1 d . . . . .
C2L C 0.9377(2) 0.5953(5) 0.6894(5) 0.0208(10) Uani 1 1 d . . . . .
H2LA H 0.9705 0.6113 0.6409 0.031 Uiso 1 1 calc R U . . .
H2LB H 0.9505 0.5494 0.7668 0.031 Uiso 1 1 calc R U . . .
H2LC H 0.9206 0.6748 0.7119 0.031 Uiso 1 1 calc R U . . .
C3L C 0.8750(2) 0.5880(5) 0.4865(5) 0.0224(11) Uani 1 1 d . . . . .
H3LA H 0.9085 0.5998 0.4388 0.034 Uiso 1 1 calc R U . . .
H3LB H 0.8592 0.6695 0.5064 0.034 Uiso 1 1 calc R U . . .
H3LC H 0.8459 0.5396 0.4354 0.034 Uiso 1 1 calc R U . . .
C4L C 0.9180(2) 0.3900(5) 0.5791(5) 0.0215(10) Uani 1 1 d . . . . .
H4LA H 0.9546 0.4016 0.5429 0.032 Uiso 1 1 calc R U . . .
H4LB H 0.8912 0.3461 0.5181 0.032 Uiso 1 1 calc R U . . .
H4LC H 0.9242 0.3408 0.6570 0.032 Uiso 1 1 calc R U . . .
C5L C 0.7958(2) 0.3512(5) 0.6343(4) 0.0169(9) Uani 1 1 d . . . . .
H5LA H 0.8209 0.2815 0.6623 0.025 Uiso 1 1 calc R U . . .
H5LB H 0.7914 0.3543 0.5416 0.025 Uiso 1 1 calc R U . . .
H5LC H 0.7581 0.3395 0.6658 0.025 Uiso 1 1 calc R U . . .
P2L P 0.86047(5) 0.70778(11) 0.95116(10) 0.0134(2) Uani 1 1 d . . . . .
O1L O 0.83618(14) 0.7511(3) 0.8220(3) 0.0161(7) Uani 1 1 d . . . . .
C6L C 0.8142(2) 0.7452(4) 1.0758(4) 0.0169(10) Uani 1 1 d . . . . .
C7L C 0.7960(2) 0.8819(5) 1.0537(4) 0.0210(10) Uani 1 1 d . . . . .
H7LA H 0.7710 0.9072 1.1183 0.032 Uiso 1 1 calc R U . . .
H7LB H 0.7753 0.8903 0.9696 0.032 Uiso 1 1 calc R U . . .
H7LC H 0.8301 0.9352 1.0593 0.032 Uiso 1 1 calc R U . . .
C8L C 0.8469(2) 0.7293(5) 1.2082(4) 0.0233(11) Uani 1 1 d . . . . .
H8LA H 0.8210 0.7463 1.2734 0.035 Uiso 1 1 calc R U . . .
H8LB H 0.8792 0.7877 1.2175 0.035 Uiso 1 1 calc R U . . .
H8LC H 0.8613 0.6436 1.2176 0.035 Uiso 1 1 calc R U . . .
C9L C 0.7617(2) 0.6592(6) 1.0624(4) 0.0217(9) Uani 1 1 d . . . . .
H9LA H 0.7345 0.6852 1.1221 0.033 Uiso 1 1 calc R U . . .
H9LB H 0.7738 0.5730 1.0808 0.033 Uiso 1 1 calc R U . . .
H9LC H 0.7432 0.6642 0.9758 0.033 Uiso 1 1 calc R U . . .
C10L C 0.9285(2) 0.7796(5) 0.9921(5) 0.0224(11) Uani 1 1 d . . . . .
H10A H 0.9536 0.7642 0.9249 0.034 Uiso 1 1 calc R U . . .
H10B H 0.9459 0.7444 1.0719 0.034 Uiso 1 1 calc R U . . .
H10C H 0.9233 0.8697 1.0020 0.034 Uiso 1 1 calc R U . . .
C11L C 0.85915(19) 0.4514(4) 0.8561(4) 0.0133(9) Uani 1 1 d . . . . .
C12L C 0.87495(19) 0.5397(4) 0.9558(4) 0.0148(9) Uani 1 1 d . . . . .
N13L N 0.90389(16) 0.5053(4) 1.0628(3) 0.0162(8) Uani 1 1 d . . . . .
C14L C 0.91685(19) 0.3828(5) 1.0789(4) 0.0160(9) Uani 1 1 d . . . . .
C15L C 0.9481(2) 0.3411(5) 1.1924(4) 0.0196(9) Uani 1 1 d . . . . .
H15A H 0.9594 0.3991 1.2576 0.023 Uiso 1 1 calc R U . . .
C16L C 0.9616(2) 0.2192(5) 1.2077(5) 0.0208(10) Uani 1 1 d . . . . .
H16A H 0.9829 0.1922 1.2834 0.025 Uiso 1 1 calc R U . . .
C17L C 0.9444(2) 0.1312(5) 1.1117(5) 0.0225(11) Uani 1 1 d . . . . .
H17A H 0.9544 0.0459 1.1238 0.027 Uiso 1 1 calc R U . . .
C18L C 0.9134(2) 0.1678(5) 1.0014(4) 0.0218(9) Uani 1 1 d . . . . .
H18A H 0.9013 0.1079 0.9384 0.026 Uiso 1 1 calc R U . . .
C19L C 0.8998(2) 0.2948(5) 0.9828(4) 0.0166(9) Uani 1 1 d . . . . .
N20L N 0.87139(16) 0.3324(4) 0.8711(3) 0.0158(8) Uani 1 1 d . . . . .
C1 C 0.7063(2) 0.5799(4) 0.5940(4) 0.0142(9) Uani 1 1 d . . . . .
C2 C 0.6543(2) 0.5559(4) 0.6414(5) 0.0190(10) Uani 1 1 d . . . . .
H2A H 0.6503 0.5718 0.7282 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6078(2) 0.5088(5) 0.5643(5) 0.0223(10) Uani 1 1 d . . . . .
H3A H 0.5725 0.4928 0.5984 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6137(2) 0.4852(4) 0.4362(5) 0.0188(10) Uani 1 1 d . . . . .
C5 C 0.6664(2) 0.5047(5) 0.3882(4) 0.0198(10) Uani 1 1 d . . . . .
H5A H 0.6711 0.4858 0.3022 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7123(2) 0.5522(5) 0.4669(5) 0.0192(10) Uani 1 1 d . . . . .
H6A H 0.7481 0.5658 0.4339 0.023 Uiso 1 1 calc R U . . .
C7 C 0.5651(2) 0.4441(5) 0.3536(5) 0.0211(10) Uani 1 1 d . . . . .
N8 N 0.5257(2) 0.4148(4) 0.2889(4) 0.0294(10) 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 C1 1.995(5) . ?
Pd1 O1L 2.142(3) . ?
Pd1 P1L 2.2451(11) . ?
Pd1 Br1 2.4851(5) . ?
P1L C5L 1.810(5) . ?
P1L C11L 1.859(5) . ?
P1L C1L 1.885(5) . ?
C1L C2L 1.529(7) . ?
C1L C3L 1.530(7) . ?
C1L C4L 1.537(7) . ?
C2L H2LA 0.9800 . ?
C2L H2LB 0.9800 . ?
C2L H2LC 0.9800 . ?
C3L H3LA 0.9800 . ?
C3L H3LB 0.9800 . ?
C3L H3LC 0.9800 . ?
C4L H4LA 0.9800 . ?
C4L H4LB 0.9800 . ?
C4L H4LC 0.9800 . ?
C5L H5LA 0.9800 . ?
C5L H5LB 0.9800 . ?
C5L H5LC 0.9800 . ?
P2L O1L 1.508(3) . ?
P2L C10L 1.788(5) . ?
P2L C6L 1.830(5) . ?
P2L C12L 1.833(5) . ?
C6L C9L 1.534(7) . ?
C6L C7L 1.538(7) . ?
C6L C8L 1.546(6) . ?
C7L H7LA 0.9800 . ?
C7L H7LB 0.9800 . ?
C7L H7LC 0.9800 . ?
C8L H8LA 0.9800 . ?
C8L H8LB 0.9800 . ?
C8L H8LC 0.9800 . ?
C9L H9LA 0.9800 . ?
C9L H9LB 0.9800 . ?
C9L H9LC 0.9800 . ?
C10L H10A 0.9800 . ?
C10L H10B 0.9800 . ?
C10L H10C 0.9800 . ?
C11L N20L 1.314(6) . ?
C11L C12L 1.442(6) . ?
C12L N13L 1.319(6) . ?
N13L C14L 1.355(6) . ?
C14L C19L 1.420(7) . ?
C14L C15L 1.421(6) . ?
C15L C16L 1.351(7) . ?
C15L H15A 0.9500 . ?
C16L C17L 1.419(7) . ?
C16L H16A 0.9500 . ?
C17L C18L 1.376(7) . ?
C17L H17A 0.9500 . ?
C18L C19L 1.409(7) . ?
C18L H18A 0.9500 . ?
C19L N20L 1.364(6) . ?
C1 C2 1.384(7) . ?
C1 C6 1.401(7) . ?
C2 C3 1.395(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.402(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.397(7) . ?
C4 C7 1.439(7) . ?
C5 C6 1.393(7) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 N8 1.143(7) . ?

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
C1 Pd1 O1L 178.84(17) . . ?
C1 Pd1 P1L 92.44(13) . . ?
O1L Pd1 P1L 87.90(9) . . ?
C1 Pd1 Br1 89.16(13) . . ?
O1L Pd1 Br1 90.58(9) . . ?
P1L Pd1 Br1 175.72(3) . . ?
C5L P1L C11L 103.0(2) . . ?
C5L P1L C1L 104.8(2) . . ?
C11L P1L C1L 101.2(2) . . ?
C5L P1L Pd1 117.85(16) . . ?
C11L P1L Pd1 110.90(14) . . ?
C1L P1L Pd1 116.96(16) . . ?
C2L C1L C3L 109.1(4) . . ?
C2L C1L C4L 110.2(4) . . ?
C3L C1L C4L 109.9(4) . . ?
C2L C1L P1L 110.4(3) . . ?
C3L C1L P1L 107.6(3) . . ?
C4L C1L P1L 109.6(3) . . ?
C1L C2L H2LA 109.5 . . ?
C1L C2L H2LB 109.5 . . ?
H2LA C2L H2LB 109.5 . . ?
C1L C2L H2LC 109.5 . . ?
H2LA C2L H2LC 109.5 . . ?
H2LB C2L H2LC 109.5 . . ?
C1L C3L H3LA 109.5 . . ?
C1L C3L H3LB 109.5 . . ?
H3LA C3L H3LB 109.5 . . ?
C1L C3L H3LC 109.5 . . ?
H3LA C3L H3LC 109.5 . . ?
H3LB C3L H3LC 109.5 . . ?
C1L C4L H4LA 109.5 . . ?
C1L C4L H4LB 109.5 . . ?
H4LA C4L H4LB 109.5 . . ?
C1L C4L H4LC 109.5 . . ?
H4LA C4L H4LC 109.5 . . ?
H4LB C4L H4LC 109.5 . . ?
P1L C5L H5LA 109.5 . . ?
P1L C5L H5LB 109.5 . . ?
H5LA C5L H5LB 109.5 . . ?
P1L C5L H5LC 109.5 . . ?
H5LA C5L H5LC 109.5 . . ?
H5LB C5L H5LC 109.5 . . ?
O1L P2L C10L 109.9(2) . . ?
O1L P2L C6L 113.0(2) . . ?
C10L P2L C6L 107.8(2) . . ?
O1L P2L C12L 112.4(2) . . ?
C10L P2L C12L 105.0(2) . . ?
C6L P2L C12L 108.5(2) . . ?
P2L O1L Pd1 125.59(19) . . ?
C9L C6L C7L 110.5(4) . . ?
C9L C6L C8L 110.0(4) . . ?
C7L C6L C8L 110.5(4) . . ?
C9L C6L P2L 109.0(3) . . ?
C7L C6L P2L 105.9(3) . . ?
C8L C6L P2L 110.8(3) . . ?
C6L C7L H7LA 109.5 . . ?
C6L C7L H7LB 109.5 . . ?
H7LA C7L H7LB 109.5 . . ?
C6L C7L H7LC 109.5 . . ?
H7LA C7L H7LC 109.5 . . ?
H7LB C7L H7LC 109.5 . . ?
C6L C8L H8LA 109.5 . . ?
C6L C8L H8LB 109.5 . . ?
H8LA C8L H8LB 109.5 . . ?
C6L C8L H8LC 109.5 . . ?
H8LA C8L H8LC 109.5 . . ?
H8LB C8L H8LC 109.5 . . ?
C6L C9L H9LA 109.5 . . ?
C6L C9L H9LB 109.5 . . ?
H9LA C9L H9LB 109.5 . . ?
C6L C9L H9LC 109.5 . . ?
H9LA C9L H9LC 109.5 . . ?
H9LB C9L H9LC 109.5 . . ?
P2L C10L H10A 109.5 . . ?
P2L C10L H10B 109.5 . . ?
H10A C10L H10B 109.5 . . ?
P2L C10L H10C 109.5 . . ?
H10A C10L H10C 109.5 . . ?
H10B C10L H10C 109.5 . . ?
N20L C11L C12L 120.7(4) . . ?
N20L C11L P1L 115.2(3) . . ?
C12L C11L P1L 123.9(3) . . ?
N13L C12L C11L 121.6(4) . . ?
N13L C12L P2L 112.2(3) . . ?
C11L C12L P2L 126.2(3) . . ?
C12L N13L C14L 118.1(4) . . ?
N13L C14L C19L 120.5(4) . . ?
N13L C14L C15L 120.2(4) . . ?
C19L C14L C15L 119.3(5) . . ?
C16L C15L C14L 120.2(5) . . ?
C16L C15L H15A 119.9 . . ?
C14L C15L H15A 119.9 . . ?
C15L C16L C17L 120.6(4) . . ?
C15L C16L H16A 119.7 . . ?
C17L C16L H16A 119.7 . . ?
C18L C17L C16L 120.9(5) . . ?
C18L C17L H17A 119.5 . . ?
C16L C17L H17A 119.5 . . ?
C17L C18L C19L 119.3(5) . . ?
C17L C18L H18A 120.3 . . ?
C19L C18L H18A 120.3 . . ?
N20L C19L C18L 119.6(4) . . ?
N20L C19L C14L 120.6(4) . . ?
C18L C19L C14L 119.8(4) . . ?
C11L N20L C19L 118.4(4) . . ?
C2 C1 C6 118.7(4) . . ?
C2 C1 Pd1 119.2(3) . . ?
C6 C1 Pd1 122.0(4) . . ?
C1 C2 C3 121.4(5) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 C7 120.0(5) . . ?
C3 C4 C7 120.2(5) . . ?
C6 C5 C4 119.7(4) . . ?
C6 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
C5 C6 C1 120.9(5) . . ?
C5 C6 H6A 119.5 . . ?
C1 C6 H6A 119.5 . . ?
N8 C7 C4 177.8(5) . . ?

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
C5L P1L C1L C2L -153.1(4) . . . . ?
C11L P1L C1L C2L -46.2(4) . . . . ?
Pd1 P1L C1L C2L 74.4(4) . . . . ?
C5L P1L C1L C3L 88.0(4) . . . . ?
C11L P1L C1L C3L -165.2(3) . . . . ?
Pd1 P1L C1L C3L -44.6(4) . . . . ?
C5L P1L C1L C4L -31.5(4) . . . . ?
C11L P1L C1L C4L 75.4(3) . . . . ?
Pd1 P1L C1L C4L -164.0(3) . . . . ?
C10L P2L O1L Pd1 162.4(2) . . . . ?
C6L P2L O1L Pd1 -77.2(3) . . . . ?
C12L P2L O1L Pd1 45.9(3) . . . . ?
O1L P2L C6L C9L 72.8(4) . . . . ?
C10L P2L C6L C9L -165.6(3) . . . . ?
C12L P2L C6L C9L -52.5(4) . . . . ?
O1L P2L C6L C7L -46.1(4) . . . . ?
C10L P2L C6L C7L 75.6(4) . . . . ?
C12L P2L C6L C7L -171.3(3) . . . . ?
O1L P2L C6L C8L -165.9(3) . . . . ?
C10L P2L C6L C8L -44.3(4) . . . . ?
C12L P2L C6L C8L 68.8(4) . . . . ?
C5L P1L C11L N20L 23.6(4) . . . . ?
C1L P1L C11L N20L -84.7(4) . . . . ?
Pd1 P1L C11L N20L 150.5(3) . . . . ?
C5L P1L C11L C12L -161.9(4) . . . . ?
C1L P1L C11L C12L 89.9(4) . . . . ?
Pd1 P1L C11L C12L -34.9(4) . . . . ?
N20L C11L C12L N13L 2.6(7) . . . . ?
P1L C11L C12L N13L -171.7(3) . . . . ?
N20L C11L C12L P2L -179.2(3) . . . . ?
P1L C11L C12L P2L 6.5(6) . . . . ?
O1L P2L C12L N13L 170.6(3) . . . . ?
C10L P2L C12L N13L 51.1(4) . . . . ?
C6L P2L C12L N13L -63.8(4) . . . . ?
O1L P2L C12L C11L -7.7(5) . . . . ?
C10L P2L C12L C11L -127.2(4) . . . . ?
C6L P2L C12L C11L 117.9(4) . . . . ?
C11L C12L N13L C14L -2.3(6) . . . . ?
P2L C12L N13L C14L 179.3(3) . . . . ?
C12L N13L C14L C19L 0.2(6) . . . . ?
C12L N13L C14L C15L 179.8(4) . . . . ?
N13L C14L C15L C16L -179.1(4) . . . . ?
C19L C14L C15L C16L 0.5(7) . . . . ?
C14L C15L C16L C17L -0.7(7) . . . . ?
C15L C16L C17L C18L -0.3(8) . . . . ?
C16L C17L C18L C19L 1.4(7) . . . . ?
C17L C18L C19L N20L 176.9(4) . . . . ?
C17L C18L C19L C14L -1.6(7) . . . . ?
N13L C14L C19L N20L 1.8(7) . . . . ?
C15L C14L C19L N20L -177.8(4) . . . . ?
N13L C14L C19L C18L -179.8(4) . . . . ?
C15L C14L C19L C18L 0.6(7) . . . . ?
C12L C11L N20L C19L -0.5(6) . . . . ?
P1L C11L N20L C19L 174.3(3) . . . . ?
C18L C19L N20L C11L 180.0(4) . . . . ?
C14L C19L N20L C11L -1.5(6) . . . . ?
C6 C1 C2 C3 -2.1(7) . . . . ?
Pd1 C1 C2 C3 174.6(4) . . . . ?
C1 C2 C3 C4 0.0(8) . . . . ?
C2 C3 C4 C5 2.3(7) . . . . ?
C2 C3 C4 C7 -176.1(5) . . . . ?
C3 C4 C5 C6 -2.5(7) . . . . ?
C7 C4 C5 C6 175.9(5) . . . . ?
C4 C5 C6 C1 0.4(7) . . . . ?
C2 C1 C6 C5 1.9(7) . . . . ?
Pd1 C1 C6 C5 -174.7(4) . . . . ?

_refine_diff_density_max         0.778
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
