# Electronic Supplementary Material (ESI) for Catalysis Science & Technology # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 1486 loop_ _publ_author_name 'Fuentes, Jose' 'Slawin, Alexandra' 'Clarke, Matthew' _publ_contact_author_name 'Clarke, Matthew' _publ_contact_author_email matthew.clarke@st-andrews.ac.uk _publ_section_title ; Application of Palladium(monophosphine)(allyl)chloride complexes as catalysts for the alkoxycarbonylation of styrene; the use of 1,3,5,7-tetramethyl-6-phenyl-2,4, 8-trioxo-6-phospha-adamantane as ligand enables successful Pd catalysed tert-butoxycarbonylation of styrene. ; # Attachment '- 6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 859192' #TrackingRef '- 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H26 Cl O3 P Pd' _chemical_formula_sum 'C19 H26 Cl O3 P Pd' _chemical_formula_weight 475.22 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8175(16) _cell_length_b 16.296(3) _cell_length_c 16.654(3) _cell_angle_alpha 100.40(3) _cell_angle_beta 100.58(3) _cell_angle_gamma 102.97(3) _cell_volume 1977.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6439 _cell_measurement_theta_min 1.6099 _cell_measurement_theta_max 28.6859 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5130 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13083 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0997 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.35 _reflns_number_total 7024 _reflns_number_gt 5419 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7024 _refine_ls_number_parameters 451 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1561 _refine_ls_wR_factor_gt 0.1431 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.25607(6) 0.31080(3) 0.66091(3) 0.01644(16) Uani 1 1 d . . . Cl1 Cl 0.5424(2) 0.32171(10) 0.63112(10) 0.0220(4) Uani 1 1 d . . . P1 P 0.3160(2) 0.45382(10) 0.72872(10) 0.0149(4) Uani 1 1 d . . . C1 C 0.1524(10) 0.1733(5) 0.6037(5) 0.0373(19) Uani 1 1 d U . . H1A H 0.2372 0.2124 0.5849 0.045 Uiso 1 1 calc R . . H1B H 0.1481 0.1135 0.5929 0.045 Uiso 1 1 calc R . . C2 C 0.0432(15) 0.2014(7) 0.6440(6) 0.072(3) Uani 1 1 d U . . H2A H -0.0277 0.1519 0.6564 0.087 Uiso 1 1 calc R . . C3 C -0.0130(14) 0.2634(7) 0.6744(6) 0.070(3) Uani 1 1 d U . . H3A H 0.0395 0.3202 0.6693 0.084 Uiso 1 1 calc R . . H3B H -0.1083 0.2537 0.7026 0.084 Uiso 1 1 calc R . . C4 C 0.1258(8) 0.4928(4) 0.7614(4) 0.0172(14) Uani 1 1 d . . . O5 O 0.0577(6) 0.4373(3) 0.8146(2) 0.0195(10) Uani 1 1 d . . . C6 C 0.1792(8) 0.4464(4) 0.8937(4) 0.0184(14) Uani 1 1 d . . . C7 C 0.3493(8) 0.4205(4) 0.8823(4) 0.0143(13) Uani 1 1 d . . . H7A H 0.3163 0.3600 0.8492 0.017 Uiso 1 1 calc R . . H7B H 0.4248 0.4233 0.9380 0.017 Uiso 1 1 calc R . . C8 C 0.4594(8) 0.4804(4) 0.8369(4) 0.0170(14) Uani 1 1 d . . . C9 C 0.1949(9) 0.5858(4) 0.8136(4) 0.0185(14) Uani 1 1 d . . . H9A H 0.2585 0.6229 0.7813 0.022 Uiso 1 1 calc R . . H9B H 0.0913 0.6076 0.8249 0.022 Uiso 1 1 calc R . . C10 C 0.3221(9) 0.5918(4) 0.8958(4) 0.0208(14) Uani 1 1 d . . . O11 O 0.2314(6) 0.5344(3) 0.9394(3) 0.0195(10) Uani 1 1 d . . . O12 O 0.4845(6) 0.5690(3) 0.8813(2) 0.0166(9) Uani 1 1 d . . . C13 C -0.0271(8) 0.4814(4) 0.6876(4) 0.0200(14) Uani 1 1 d . . . H13A H -0.1239 0.5025 0.7070 0.030 Uiso 1 1 calc R . . H13B H -0.0735 0.4200 0.6593 0.030 Uiso 1 1 calc R . . H13C H 0.0162 0.5144 0.6482 0.030 Uiso 1 1 calc R . . C14 C 0.0724(9) 0.3927(4) 0.9404(4) 0.0227(15) Uani 1 1 d . . . H14A H -0.0358 0.4123 0.9453 0.034 Uiso 1 1 calc R . . H14B H 0.1460 0.3987 0.9965 0.034 Uiso 1 1 calc R . . H14C H 0.0366 0.3319 0.9099 0.034 Uiso 1 1 calc R . . C15 C 0.6464(8) 0.4682(4) 0.8412(4) 0.0198(14) Uani 1 1 d . . . H15A H 0.7136 0.4834 0.9000 0.030 Uiso 1 1 calc R . . H15B H 0.7097 0.5057 0.8101 0.030 Uiso 1 1 calc R . . H15C H 0.6374 0.4076 0.8164 0.030 Uiso 1 1 calc R . . C16 C 0.3840(10) 0.6814(4) 0.9514(4) 0.0265(16) Uani 1 1 d . . . H16A H 0.4659 0.6815 1.0035 0.040 Uiso 1 1 calc R . . H16B H 0.2792 0.6997 0.9644 0.040 Uiso 1 1 calc R . . H16C H 0.4473 0.7215 0.9224 0.040 Uiso 1 1 calc R . . C17 C 0.4136(8) 0.5322(4) 0.6725(4) 0.0166(14) Uani 1 1 d . . . C18 C 0.3367(8) 0.5141(4) 0.5863(4) 0.0203(14) Uani 1 1 d . . . H18A H 0.2433 0.4625 0.5607 0.024 Uiso 1 1 calc R . . C19 C 0.3954(9) 0.5708(4) 0.5380(4) 0.0214(15) Uani 1 1 d . . . H19A H 0.3408 0.5593 0.4798 0.026 Uiso 1 1 calc R . . C20 C 0.5342(8) 0.6441(4) 0.5759(4) 0.0216(15) Uani 1 1 d . . . H20A H 0.5754 0.6832 0.5432 0.026 Uiso 1 1 calc R . . C21 C 0.6135(9) 0.6617(4) 0.6594(4) 0.0223(15) Uani 1 1 d . . . H21A H 0.7111 0.7119 0.6841 0.027 Uiso 1 1 calc R . . C22 C 0.5520(9) 0.6066(4) 0.7084(4) 0.0201(14) Uani 1 1 d . . . H22A H 0.6051 0.6200 0.7669 0.024 Uiso 1 1 calc R . . Pd31 Pd 0.43859(6) 1.09433(3) 0.79921(3) 0.01908(17) Uani 1 1 d . . . Cl31 Cl 0.2135(2) 1.14416(12) 0.85521(11) 0.0305(4) Uani 1 1 d . . . P31 P 0.2857(2) 0.94940(11) 0.76487(10) 0.0184(4) Uani 1 1 d . . . C31 C 0.6268(9) 1.2228(5) 0.8221(4) 0.0304(17) Uani 1 1 d U . . H31A H 0.6289 1.2092 0.8753 0.036 Uiso 1 1 calc R . . H31B H 0.6067 1.2763 0.8136 0.036 Uiso 1 1 calc R . . C32 C 0.6517(15) 1.1673(7) 0.7599(7) 0.073(3) Uani 1 1 d U . . H32A H 0.6475 1.1857 0.7088 0.087 Uiso 1 1 calc R . . C33 C 0.6813(9) 1.0903(5) 0.7573(4) 0.0285(16) Uani 1 1 d U . . H33A H 0.6874 1.0672 0.8059 0.034 Uiso 1 1 calc R . . H33B H 0.6966 1.0581 0.7068 0.034 Uiso 1 1 calc R . . C34 C 0.4105(8) 0.8671(4) 0.7343(4) 0.0211(15) Uani 1 1 d . . . O35 O 0.4834(6) 0.8895(3) 0.6642(3) 0.0214(10) Uani 1 1 d . . . C36 C 0.3539(8) 0.8779(4) 0.5882(4) 0.0189(14) Uani 1 1 d . . . C37 C 0.2323(9) 0.9388(4) 0.5984(4) 0.0211(15) Uani 1 1 d . . . H37A H 0.3077 0.9994 0.6183 0.025 Uiso 1 1 calc R . . H37B H 0.1516 0.9334 0.5434 0.025 Uiso 1 1 calc R . . C38 C 0.1198(8) 0.9174(4) 0.6606(4) 0.0175(14) Uani 1 1 d . . . C39 C 0.2806(9) 0.7766(4) 0.7023(4) 0.0258(16) Uani 1 1 d . . . H39A H 0.3505 0.7337 0.6917 0.031 Uiso 1 1 calc R . . H39B H 0.2164 0.7627 0.7462 0.031 Uiso 1 1 calc R . . C40 C 0.1452(9) 0.7692(4) 0.6234(4) 0.0221(15) Uani 1 1 d . . . O41 O 0.2402(6) 0.7926(3) 0.5614(3) 0.0208(10) Uani 1 1 d . . . O42 O 0.0294(6) 0.8257(3) 0.6372(3) 0.0183(10) Uani 1 1 d . . . C43 C 0.5673(9) 0.8714(5) 0.8029(4) 0.0292(17) Uani 1 1 d . . . H43A H 0.6279 0.8274 0.7843 0.044 Uiso 1 1 calc R . . H43B H 0.5243 0.8606 0.8527 0.044 Uiso 1 1 calc R . . H43C H 0.6524 0.9289 0.8167 0.044 Uiso 1 1 calc R . . C44 C 0.4612(9) 0.8908(4) 0.5215(4) 0.0246(16) Uani 1 1 d . . . H44A H 0.5359 0.8500 0.5185 0.037 Uiso 1 1 calc R . . H44B H 0.5389 0.9502 0.5363 0.037 Uiso 1 1 calc R . . H44C H 0.3777 0.8806 0.4668 0.037 Uiso 1 1 calc R . . C45 C -0.0325(8) 0.9620(4) 0.6611(4) 0.0186(14) Uani 1 1 d . . . H45A H -0.1162 0.9435 0.6056 0.028 Uiso 1 1 calc R . . H45B H 0.0183 1.0249 0.6745 0.028 Uiso 1 1 calc R . . H45C H -0.0975 0.9462 0.7034 0.028 Uiso 1 1 calc R . . C46 C 0.0213(10) 0.6805(4) 0.5841(5) 0.0292(17) Uani 1 1 d . . . H46A H -0.0622 0.6824 0.5332 0.044 Uiso 1 1 calc R . . H46B H -0.0476 0.6610 0.6239 0.044 Uiso 1 1 calc R . . H46C H 0.0927 0.6401 0.5695 0.044 Uiso 1 1 calc R . . C47 C 0.1791(8) 0.9127(4) 0.8443(4) 0.0213(15) Uani 1 1 d . . . C48 C 0.2551(11) 0.9579(5) 0.9276(4) 0.0379(19) Uani 1 1 d . . . H48A H 0.3554 1.0073 0.9402 0.046 Uiso 1 1 calc R . . C49 C 0.1852(14) 0.9311(6) 0.9922(5) 0.053(3) Uani 1 1 d . . . H49A H 0.2403 0.9614 1.0487 0.064 Uiso 1 1 calc R . . C50 C 0.0365(11) 0.8609(6) 0.9752(5) 0.042(2) Uani 1 1 d . . . H50A H -0.0109 0.8438 1.0200 0.050 Uiso 1 1 calc R . . C51 C -0.0427(10) 0.8160(6) 0.8947(5) 0.041(2) Uani 1 1 d . . . H51A H -0.1446 0.7675 0.8834 0.049 Uiso 1 1 calc R . . C52 C 0.0273(9) 0.8417(5) 0.8286(4) 0.0286(17) Uani 1 1 d . . . H52A H -0.0287 0.8106 0.7724 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.0152(3) 0.0157(3) 0.0175(3) 0.0033(2) 0.0041(2) 0.0024(2) Cl1 0.0194(9) 0.0255(9) 0.0227(9) 0.0056(7) 0.0080(7) 0.0064(7) P1 0.0119(8) 0.0171(9) 0.0163(9) 0.0043(6) 0.0047(6) 0.0034(7) C1 0.037(2) 0.036(2) 0.038(2) 0.0074(11) 0.0095(11) 0.0090(11) C2 0.072(3) 0.072(3) 0.074(3) 0.0153(12) 0.0188(12) 0.0186(13) C3 0.068(3) 0.069(3) 0.071(3) 0.0144(12) 0.0188(12) 0.0174(13) C4 0.015(3) 0.028(4) 0.015(3) 0.012(3) 0.008(3) 0.009(3) O5 0.016(2) 0.024(3) 0.020(2) 0.0079(18) 0.0025(18) 0.008(2) C6 0.019(3) 0.017(4) 0.021(3) 0.007(3) 0.002(3) 0.008(3) C7 0.016(3) 0.018(3) 0.011(3) 0.006(2) 0.001(2) 0.009(3) C8 0.020(3) 0.014(3) 0.017(3) 0.001(2) 0.007(3) 0.004(3) C9 0.021(4) 0.024(4) 0.020(3) 0.013(3) 0.011(3) 0.015(3) C10 0.023(4) 0.020(4) 0.020(4) 0.002(3) 0.005(3) 0.010(3) O11 0.025(3) 0.021(3) 0.018(2) 0.0071(18) 0.0097(19) 0.010(2) O12 0.018(2) 0.014(2) 0.019(2) 0.0028(17) 0.0034(18) 0.0084(19) C13 0.014(3) 0.027(4) 0.023(4) 0.011(3) 0.010(3) 0.006(3) C14 0.022(4) 0.034(4) 0.017(3) 0.013(3) 0.009(3) 0.008(3) C15 0.014(3) 0.023(4) 0.022(4) 0.005(3) 0.005(3) 0.006(3) C16 0.034(4) 0.016(4) 0.029(4) 0.002(3) 0.004(3) 0.012(3) C17 0.014(3) 0.024(4) 0.016(3) 0.005(3) 0.009(3) 0.009(3) C18 0.016(3) 0.023(4) 0.019(4) 0.000(3) 0.002(3) 0.004(3) C19 0.020(4) 0.024(4) 0.026(4) 0.013(3) 0.008(3) 0.010(3) C20 0.019(4) 0.023(4) 0.034(4) 0.018(3) 0.018(3) 0.009(3) C21 0.020(4) 0.017(4) 0.031(4) 0.005(3) 0.011(3) 0.004(3) C22 0.021(4) 0.022(4) 0.017(3) 0.002(3) 0.003(3) 0.009(3) Pd31 0.0168(3) 0.0228(3) 0.0186(3) 0.0051(2) 0.0041(2) 0.0069(2) Cl31 0.0300(10) 0.0357(11) 0.0318(10) 0.0066(8) 0.0149(8) 0.0156(8) P31 0.0144(9) 0.0239(10) 0.0189(9) 0.0068(7) 0.0042(7) 0.0072(7) C31 0.0303(19) 0.0310(19) 0.0297(19) 0.0066(10) 0.0086(10) 0.0069(10) C32 0.072(3) 0.073(3) 0.073(3) 0.0169(12) 0.0184(12) 0.0187(13) C33 0.0282(18) 0.0285(19) 0.0292(18) 0.0063(10) 0.0079(10) 0.0078(10) C34 0.014(3) 0.036(4) 0.022(4) 0.019(3) 0.006(3) 0.013(3) O35 0.016(2) 0.025(3) 0.027(3) 0.0102(19) 0.0084(19) 0.007(2) C36 0.018(3) 0.021(4) 0.019(3) 0.008(3) 0.006(3) 0.004(3) C37 0.020(4) 0.021(4) 0.019(4) 0.004(3) 0.000(3) 0.005(3) C38 0.011(3) 0.015(3) 0.025(4) 0.002(3) 0.003(3) 0.002(3) C39 0.026(4) 0.026(4) 0.034(4) 0.011(3) 0.013(3) 0.015(3) C40 0.017(4) 0.021(4) 0.034(4) 0.013(3) 0.011(3) 0.005(3) O41 0.021(3) 0.017(2) 0.028(3) 0.0087(19) 0.012(2) 0.004(2) O42 0.019(2) 0.016(2) 0.023(2) 0.0067(18) 0.0077(19) 0.0068(19) C43 0.027(4) 0.037(5) 0.030(4) 0.013(3) 0.004(3) 0.018(3) C44 0.030(4) 0.020(4) 0.024(4) 0.002(3) 0.011(3) 0.007(3) C45 0.012(3) 0.019(4) 0.025(4) 0.005(3) 0.005(3) 0.005(3) C46 0.033(4) 0.017(4) 0.041(4) 0.010(3) 0.018(3) 0.003(3) C47 0.015(3) 0.027(4) 0.027(4) 0.011(3) 0.006(3) 0.011(3) C48 0.047(5) 0.038(5) 0.028(4) 0.010(3) 0.011(4) 0.006(4) C49 0.088(8) 0.051(6) 0.024(4) 0.016(4) 0.022(4) 0.012(5) C50 0.053(6) 0.058(6) 0.035(5) 0.032(4) 0.029(4) 0.023(5) C51 0.027(4) 0.059(6) 0.046(5) 0.029(4) 0.014(4) 0.016(4) C52 0.016(4) 0.049(5) 0.027(4) 0.018(3) 0.011(3) 0.007(3) _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 C2 2.084(12) . ? Pd1 C3 2.140(11) . ? Pd1 C1 2.171(8) . ? Pd1 P1 2.3005(18) . ? Pd1 Cl1 2.3559(17) . ? P1 C17 1.830(6) . ? P1 C8 1.858(6) . ? P1 C4 1.873(6) . ? C1 C2 1.290(12) . ? C1 H1A 0.9500 . ? C1 H1B 0.9500 . ? C2 C3 1.252(13) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C3 H3B 0.9500 . ? C4 O5 1.459(7) . ? C4 C13 1.502(8) . ? C4 C9 1.526(9) . ? O5 C6 1.438(7) . ? C6 O11 1.425(7) . ? C6 C14 1.490(8) . ? C6 C7 1.517(8) . ? C7 C8 1.547(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O12 1.451(7) . ? C8 C15 1.510(8) . ? C9 C10 1.510(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O11 1.429(8) . ? C10 O12 1.450(7) . ? C10 C16 1.501(9) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C22 1.382(9) . ? C17 C18 1.399(8) . ? C18 C19 1.387(9) . ? C18 H18A 0.9500 . ? C19 C20 1.377(9) . ? C19 H19A 0.9500 . ? C20 C21 1.365(9) . ? C20 H20A 0.9500 . ? C21 C22 1.385(9) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? Pd31 C32 2.100(11) . ? Pd31 C33 2.149(7) . ? Pd31 C31 2.195(7) . ? Pd31 P31 2.308(2) . ? Pd31 Cl31 2.3657(18) . ? P31 C47 1.808(6) . ? P31 C38 1.874(6) . ? P31 C34 1.880(7) . ? C31 C32 1.320(12) . ? C31 H31A 0.9500 . ? C31 H31B 0.9500 . ? C32 C33 1.321(12) . ? C32 H32A 0.9500 . ? C33 H33A 0.9500 . ? C33 H33B 0.9500 . ? C34 O35 1.458(7) . ? C34 C43 1.494(9) . ? C34 C39 1.528(9) . ? O35 C36 1.422(7) . ? C36 O41 1.414(7) . ? C36 C44 1.526(9) . ? C36 C37 1.529(9) . ? C37 C38 1.515(9) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 O42 1.449(7) . ? C38 C45 1.528(8) . ? C39 C40 1.495(9) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 O41 1.436(7) . ? C40 O42 1.447(7) . ? C40 C46 1.502(9) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 C48 1.398(10) . ? C47 C52 1.405(9) . ? C48 C49 1.386(10) . ? C48 H48A 0.9500 . ? C49 C50 1.381(11) . ? C49 H49A 0.9500 . ? C50 C51 1.361(11) . ? C50 H50A 0.9500 . ? C51 C52 1.405(10) . ? C51 H51A 0.9500 . ? C52 H52A 0.9500 . ? 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 C2 Pd1 C3 34.5(4) . . ? C2 Pd1 C1 35.2(3) . . ? C3 Pd1 C1 69.3(3) . . ? C2 Pd1 P1 134.2(3) . . ? C3 Pd1 P1 100.2(3) . . ? C1 Pd1 P1 169.4(2) . . ? C2 Pd1 Cl1 129.6(3) . . ? C3 Pd1 Cl1 164.0(3) . . ? C1 Pd1 Cl1 94.9(2) . . ? P1 Pd1 Cl1 95.69(7) . . ? C17 P1 C8 108.5(3) . . ? C17 P1 C4 104.7(3) . . ? C8 P1 C4 94.9(3) . . ? C17 P1 Pd1 115.3(2) . . ? C8 P1 Pd1 113.5(2) . . ? C4 P1 Pd1 117.9(2) . . ? C2 C1 Pd1 68.7(6) . . ? C2 C1 H1A 120.0 . . ? Pd1 C1 H1A 55.6 . . ? C2 C1 H1B 120.0 . . ? Pd1 C1 H1B 158.1 . . ? H1A C1 H1B 120.0 . . ? C3 C2 C1 149.2(12) . . ? C3 C2 Pd1 75.3(8) . . ? C1 C2 Pd1 76.1(7) . . ? C3 C2 H2A 105.4 . . ? C1 C2 H2A 105.4 . . ? Pd1 C2 H2A 158.4 . . ? C2 C3 Pd1 70.3(7) . . ? C2 C3 H3A 120.0 . . ? Pd1 C3 H3A 54.2 . . ? C2 C3 H3B 120.0 . . ? Pd1 C3 H3B 157.3 . . ? H3A C3 H3B 120.0 . . ? O5 C4 C13 107.2(5) . . ? O5 C4 C9 108.4(5) . . ? C13 C4 C9 112.8(5) . . ? O5 C4 P1 106.1(4) . . ? C13 C4 P1 111.7(4) . . ? C9 C4 P1 110.4(4) . . ? C6 O5 C4 115.5(5) . . ? O11 C6 O5 109.7(5) . . ? O11 C6 C14 108.6(5) . . ? O5 C6 C14 105.4(5) . . ? O11 C6 C7 107.8(5) . . ? O5 C6 C7 111.9(5) . . ? C14 C6 C7 113.4(5) . . ? C6 C7 C8 111.4(5) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? O12 C8 C15 106.0(5) . . ? O12 C8 C7 107.5(5) . . ? C15 C8 C7 112.2(5) . . ? O12 C8 P1 112.9(4) . . ? C15 C8 P1 114.2(4) . . ? C7 C8 P1 103.9(4) . . ? C10 C9 C4 111.3(5) . . ? C10 C9 H9A 109.4 . . ? C4 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C4 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? O11 C10 O12 110.2(5) . . ? O11 C10 C16 108.5(5) . . ? O12 C10 C16 105.9(5) . . ? O11 C10 C9 108.6(5) . . ? O12 C10 C9 110.6(5) . . ? C16 C10 C9 113.0(5) . . ? C6 O11 C10 112.5(4) . . ? C8 O12 C10 115.7(5) . . ? C4 C13 H13A 109.5 . . ? C4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 C14 H14A 109.5 . . ? C6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 118.9(6) . . ? C22 C17 P1 125.4(5) . . ? C18 C17 P1 115.7(5) . . ? C19 C18 C17 120.6(6) . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C20 C19 C18 118.8(6) . . ? C20 C19 H19A 120.6 . . ? C18 C19 H19A 120.6 . . ? C21 C20 C19 121.3(6) . . ? C21 C20 H20A 119.4 . . ? C19 C20 H20A 119.4 . . ? C20 C21 C22 120.1(6) . . ? C20 C21 H21A 120.0 . . ? C22 C21 H21A 120.0 . . ? C17 C22 C21 120.2(6) . . ? C17 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? C32 Pd31 C33 36.2(3) . . ? C32 Pd31 C31 35.7(3) . . ? C33 Pd31 C31 67.0(3) . . ? C32 Pd31 P31 133.7(3) . . ? C33 Pd31 P31 101.44(19) . . ? C31 Pd31 P31 168.43(19) . . ? C32 Pd31 Cl31 127.3(3) . . ? C33 Pd31 Cl31 162.6(2) . . ? C31 Pd31 Cl31 95.66(19) . . ? P31 Pd31 Cl31 95.91(7) . . ? C47 P31 C38 110.6(3) . . ? C47 P31 C34 104.6(3) . . ? C38 P31 C34 93.9(3) . . ? C47 P31 Pd31 114.9(2) . . ? C38 P31 Pd31 112.2(2) . . ? C34 P31 Pd31 118.7(2) . . ? C32 C31 Pd31 68.2(6) . . ? C32 C31 H31A 120.0 . . ? Pd31 C31 H31A 73.4 . . ? C32 C31 H31B 120.0 . . ? Pd31 C31 H31B 131.1 . . ? H31A C31 H31B 120.0 . . ? C31 C32 C33 130.4(10) . . ? C31 C32 Pd31 76.1(6) . . ? C33 C32 Pd31 73.9(6) . . ? C31 C32 H32A 114.8 . . ? C33 C32 H32A 114.8 . . ? Pd31 C32 H32A 128.1 . . ? C32 C33 Pd31 69.9(6) . . ? C32 C33 H33A 120.0 . . ? Pd31 C33 H33A 72.8 . . ? C32 C33 H33B 120.0 . . ? Pd31 C33 H33B 129.8 . . ? H33A C33 H33B 120.0 . . ? O35 C34 C43 107.0(5) . . ? O35 C34 C39 107.3(5) . . ? C43 C34 C39 112.9(6) . . ? O35 C34 P31 106.2(4) . . ? C43 C34 P31 112.3(5) . . ? C39 C34 P31 110.6(4) . . ? C36 O35 C34 115.7(5) . . ? O41 C36 O35 111.9(5) . . ? O41 C36 C44 106.5(5) . . ? O35 C36 C44 106.1(5) . . ? O41 C36 C37 107.1(5) . . ? O35 C36 C37 111.2(5) . . ? C44 C36 C37 114.0(5) . . ? C38 C37 C36 110.9(5) . . ? C38 C37 H37A 109.5 . . ? C36 C37 H37A 109.5 . . ? C38 C37 H37B 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 108.1 . . ? O42 C38 C37 108.9(5) . . ? O42 C38 C45 104.7(5) . . ? C37 C38 C45 114.1(5) . . ? O42 C38 P31 112.3(4) . . ? C37 C38 P31 104.8(4) . . ? C45 C38 P31 112.1(4) . . ? C40 C39 C34 112.2(5) . . ? C40 C39 H39A 109.2 . . ? C34 C39 H39A 109.2 . . ? C40 C39 H39B 109.2 . . ? C34 C39 H39B 109.2 . . ? H39A C39 H39B 107.9 . . ? O41 C40 O42 109.1(5) . . ? O41 C40 C39 108.5(5) . . ? O42 C40 C39 111.4(5) . . ? O41 C40 C46 105.8(5) . . ? O42 C40 C46 106.0(5) . . ? C39 C40 C46 115.7(6) . . ? C36 O41 C40 111.9(4) . . ? C40 O42 C38 115.2(4) . . ? C34 C43 H43A 109.5 . . ? C34 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C34 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C36 C44 H44A 109.5 . . ? C36 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C36 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C38 C45 H45A 109.5 . . ? C38 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C38 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C40 C46 H46A 109.5 . . ? C40 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C40 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C48 C47 C52 117.7(6) . . ? C48 C47 P31 117.3(5) . . ? C52 C47 P31 124.9(5) . . ? C49 C48 C47 120.5(8) . . ? C49 C48 H48A 119.7 . . ? C47 C48 H48A 119.7 . . ? C50 C49 C48 120.7(7) . . ? C50 C49 H49A 119.7 . . ? C48 C49 H49A 119.7 . . ? C51 C50 C49 120.5(7) . . ? C51 C50 H50A 119.8 . . ? C49 C50 H50A 119.8 . . ? C50 C51 C52 119.6(8) . . ? C50 C51 H51A 120.2 . . ? C52 C51 H51A 120.2 . . ? C51 C52 C47 121.0(7) . . ? C51 C52 H52A 119.5 . . ? C47 C52 H52A 119.5 . . ? 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 C2 Pd1 P1 C17 -138.4(5) . . . . ? C3 Pd1 P1 C17 -132.4(4) . . . . ? C1 Pd1 P1 C17 -135.2(11) . . . . ? Cl1 Pd1 P1 C17 49.7(2) . . . . ? C2 Pd1 P1 C8 95.6(5) . . . . ? C3 Pd1 P1 C8 101.7(4) . . . . ? C1 Pd1 P1 C8 98.8(11) . . . . ? Cl1 Pd1 P1 C8 -76.3(2) . . . . ? C2 Pd1 P1 C4 -13.9(5) . . . . ? C3 Pd1 P1 C4 -7.9(4) . . . . ? C1 Pd1 P1 C4 -10.7(11) . . . . ? Cl1 Pd1 P1 C4 174.2(2) . . . . ? C3 Pd1 C1 C2 -7.0(7) . . . . ? P1 Pd1 C1 C2 -4.0(15) . . . . ? Cl1 Pd1 C1 C2 171.1(6) . . . . ? Pd1 C1 C2 C3 22(2) . . . . ? C1 Pd1 C2 C3 -168.4(11) . . . . ? P1 Pd1 C2 C3 10.6(9) . . . . ? Cl1 Pd1 C2 C3 -179.9(5) . . . . ? C3 Pd1 C2 C1 168.4(11) . . . . ? P1 Pd1 C2 C1 179.0(4) . . . . ? Cl1 Pd1 C2 C1 -11.5(8) . . . . ? C1 C2 C3 Pd1 -22(2) . . . . ? C1 Pd1 C3 C2 7.1(7) . . . . ? P1 Pd1 C3 C2 -172.3(6) . . . . ? Cl1 Pd1 C3 C2 0.3(15) . . . . ? C17 P1 C4 O5 -173.8(4) . . . . ? C8 P1 C4 O5 -63.2(4) . . . . ? Pd1 P1 C4 O5 56.6(4) . . . . ? C17 P1 C4 C13 69.8(5) . . . . ? C8 P1 C4 C13 -179.7(5) . . . . ? Pd1 P1 C4 C13 -59.9(5) . . . . ? C17 P1 C4 C9 -56.6(5) . . . . ? C8 P1 C4 C9 54.0(4) . . . . ? Pd1 P1 C4 C9 173.8(3) . . . . ? C13 C4 O5 C6 -173.4(5) . . . . ? C9 C4 O5 C6 -51.4(6) . . . . ? P1 C4 O5 C6 67.1(5) . . . . ? C4 O5 C6 O11 56.2(6) . . . . ? C4 O5 C6 C14 172.9(5) . . . . ? C4 O5 C6 C7 -63.4(6) . . . . ? O11 C6 C7 C8 -57.4(6) . . . . ? O5 C6 C7 C8 63.3(6) . . . . ? C14 C6 C7 C8 -177.6(5) . . . . ? C6 C7 C8 O12 51.7(6) . . . . ? C6 C7 C8 C15 167.9(5) . . . . ? C6 C7 C8 P1 -68.3(5) . . . . ? C17 P1 C8 O12 55.0(5) . . . . ? C4 P1 C8 O12 -52.3(4) . . . . ? Pd1 P1 C8 O12 -175.5(3) . . . . ? C17 P1 C8 C15 -66.3(5) . . . . ? C4 P1 C8 C15 -173.5(5) . . . . ? Pd1 P1 C8 C15 63.2(5) . . . . ? C17 P1 C8 C7 171.2(4) . . . . ? C4 P1 C8 C7 64.0(4) . . . . ? Pd1 P1 C8 C7 -59.3(4) . . . . ? O5 C4 C9 C10 50.4(6) . . . . ? C13 C4 C9 C10 168.9(5) . . . . ? P1 C4 C9 C10 -65.3(6) . . . . ? C4 C9 C10 O11 -55.9(6) . . . . ? C4 C9 C10 O12 65.1(7) . . . . ? C4 C9 C10 C16 -176.4(5) . . . . ? O5 C6 O11 C10 -60.5(6) . . . . ? C14 C6 O11 C10 -175.2(5) . . . . ? C7 C6 O11 C10 61.6(6) . . . . ? O12 C10 O11 C6 -60.2(6) . . . . ? C16 C10 O11 C6 -175.7(5) . . . . ? C9 C10 O11 C6 61.1(6) . . . . ? C15 C8 O12 C10 -171.4(5) . . . . ? C7 C8 O12 C10 -51.2(6) . . . . ? P1 C8 O12 C10 62.8(6) . . . . ? O11 C10 O12 C8 55.7(6) . . . . ? C16 C10 O12 C8 172.9(5) . . . . ? C9 C10 O12 C8 -64.4(7) . . . . ? C8 P1 C17 C22 -9.9(6) . . . . ? C4 P1 C17 C22 90.4(6) . . . . ? Pd1 P1 C17 C22 -138.4(5) . . . . ? C8 P1 C17 C18 171.2(5) . . . . ? C4 P1 C17 C18 -88.4(5) . . . . ? Pd1 P1 C17 C18 42.7(5) . . . . ? C22 C17 C18 C19 -1.4(9) . . . . ? P1 C17 C18 C19 177.5(5) . . . . ? C17 C18 C19 C20 1.7(9) . . . . ? C18 C19 C20 C21 -0.2(10) . . . . ? C19 C20 C21 C22 -1.6(10) . . . . ? C18 C17 C22 C21 -0.4(9) . . . . ? P1 C17 C22 C21 -179.2(5) . . . . ? C20 C21 C22 C17 1.9(10) . . . . ? C32 Pd31 P31 C47 156.1(5) . . . . ? C33 Pd31 P31 C47 137.0(3) . . . . ? C31 Pd31 P31 C47 134.8(10) . . . . ? Cl31 Pd31 P31 C47 -43.7(2) . . . . ? C32 Pd31 P31 C38 -76.6(5) . . . . ? C33 Pd31 P31 C38 -95.6(3) . . . . ? C31 Pd31 P31 C38 -97.8(10) . . . . ? Cl31 Pd31 P31 C38 83.7(2) . . . . ? C32 Pd31 P31 C34 31.3(5) . . . . ? C33 Pd31 P31 C34 12.2(3) . . . . ? C31 Pd31 P31 C34 10.1(10) . . . . ? Cl31 Pd31 P31 C34 -168.4(2) . . . . ? C33 Pd31 C31 C32 24.3(6) . . . . ? P31 Pd31 C31 C32 26.6(13) . . . . ? Cl31 Pd31 C31 C32 -154.9(6) . . . . ? Pd31 C31 C32 C33 -54.1(11) . . . . ? C33 Pd31 C32 C31 -140.1(9) . . . . ? P31 Pd31 C32 C31 -172.9(4) . . . . ? Cl31 Pd31 C32 C31 32.1(8) . . . . ? C31 Pd31 C32 C33 140.1(9) . . . . ? P31 Pd31 C32 C33 -32.8(8) . . . . ? Cl31 Pd31 C32 C33 172.2(4) . . . . ? C31 C32 C33 Pd31 54.9(11) . . . . ? C31 Pd31 C33 C32 -24.0(6) . . . . ? P31 Pd31 C33 C32 156.5(6) . . . . ? Cl31 Pd31 C33 C32 -21.3(10) . . . . ? C47 P31 C34 O35 174.4(4) . . . . ? C38 P31 C34 O35 62.0(4) . . . . ? Pd31 P31 C34 O35 -56.0(4) . . . . ? C47 P31 C34 C43 -69.0(5) . . . . ? C38 P31 C34 C43 178.6(5) . . . . ? Pd31 P31 C34 C43 60.7(5) . . . . ? C47 P31 C34 C39 58.2(5) . . . . ? C38 P31 C34 C39 -54.2(5) . . . . ? Pd31 P31 C34 C39 -172.1(4) . . . . ? C43 C34 O35 C36 171.9(5) . . . . ? C39 C34 O35 C36 50.4(6) . . . . ? P31 C34 O35 C36 -67.9(5) . . . . ? C34 O35 C36 O41 -55.2(7) . . . . ? C34 O35 C36 C44 -170.9(5) . . . . ? C34 O35 C36 C37 64.6(6) . . . . ? O41 C36 C37 C38 58.0(6) . . . . ? O35 C36 C37 C38 -64.6(7) . . . . ? C44 C36 C37 C38 175.6(5) . . . . ? C36 C37 C38 O42 -51.3(7) . . . . ? C36 C37 C38 C45 -167.9(5) . . . . ? C36 C37 C38 P31 69.1(5) . . . . ? C47 P31 C38 O42 -52.9(5) . . . . ? C34 P31 C38 O42 54.2(4) . . . . ? Pd31 P31 C38 O42 177.4(3) . . . . ? C47 P31 C38 C37 -171.1(4) . . . . ? C34 P31 C38 C37 -63.9(4) . . . . ? Pd31 P31 C38 C37 59.3(4) . . . . ? C47 P31 C38 C45 64.6(5) . . . . ? C34 P31 C38 C45 171.8(4) . . . . ? Pd31 P31 C38 C45 -65.0(4) . . . . ? O35 C34 C39 C40 -51.3(7) . . . . ? C43 C34 C39 C40 -169.0(6) . . . . ? P31 C34 C39 C40 64.2(6) . . . . ? C34 C39 C40 O41 56.7(7) . . . . ? C34 C39 C40 O42 -63.4(7) . . . . ? C34 C39 C40 C46 175.4(5) . . . . ? O35 C36 O41 C40 58.4(6) . . . . ? C44 C36 O41 C40 173.9(5) . . . . ? C37 C36 O41 C40 -63.7(6) . . . . ? O42 C40 O41 C36 62.3(6) . . . . ? C39 C40 O41 C36 -59.3(6) . . . . ? C46 C40 O41 C36 176.0(5) . . . . ? O41 C40 O42 C38 -55.6(6) . . . . ? C39 C40 O42 C38 64.2(6) . . . . ? C46 C40 O42 C38 -169.2(5) . . . . ? C37 C38 O42 C40 51.1(6) . . . . ? C45 C38 O42 C40 173.6(5) . . . . ? P31 C38 O42 C40 -64.6(5) . . . . ? C38 P31 C47 C48 -155.2(5) . . . . ? C34 P31 C47 C48 104.9(6) . . . . ? Pd31 P31 C47 C48 -27.0(6) . . . . ? C38 P31 C47 C52 25.7(7) . . . . ? C34 P31 C47 C52 -74.2(6) . . . . ? Pd31 P31 C47 C52 153.9(5) . . . . ? C52 C47 C48 C49 2.0(11) . . . . ? P31 C47 C48 C49 -177.2(6) . . . . ? C47 C48 C49 C50 -1.8(13) . . . . ? C48 C49 C50 C51 0.9(14) . . . . ? C49 C50 C51 C52 -0.3(12) . . . . ? C50 C51 C52 C47 0.6(11) . . . . ? C48 C47 C52 C51 -1.4(11) . . . . ? P31 C47 C52 C51 177.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 2.018 _refine_diff_density_min -1.297 _refine_diff_density_rms 0.175 # Attachment '- 7.cif' data_7 _database_code_depnum_ccdc_archive 'CCDC 859193' #TrackingRef '- 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H32 Cl O4 P Pd' _chemical_formula_sum 'C22 H32 Cl O4 P Pd' _chemical_formula_weight 533.30 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.552(3) _cell_length_b 15.094(4) _cell_length_c 16.038(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.126(7) _cell_angle_gamma 90.00 _cell_volume 2276.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 8210 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.5 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 1.028 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14007 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.36 _reflns_number_total 4147 _reflns_number_gt 3744 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^2^+5.0322P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4147 _refine_ls_number_parameters 262 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.103 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.96784(3) 0.359598(18) 0.973917(17) 0.01672(11) Uani 1 1 d . . . Cl1 Cl 0.79023(11) 0.42554(8) 0.87205(6) 0.0330(3) Uani 1 1 d . . . P1 P 0.83017(10) 0.27525(6) 1.04683(6) 0.0155(2) Uani 1 1 d . . . C1 C 1.1408(4) 0.4244(3) 0.9240(3) 0.0281(9) Uani 1 1 d U . . H1A H 1.0978 0.4676 0.9545 0.034 Uiso 1 1 calc R . . H1B H 1.1522 0.4359 0.8673 0.034 Uiso 1 1 calc R . . C2 C 1.1843(7) 0.3490(4) 0.9601(4) 0.0605(16) Uani 1 1 d U . . H2A H 1.2266 0.3077 0.9274 0.073 Uiso 1 1 calc R . . C3 C 1.1736(5) 0.3244(3) 1.0421(3) 0.0352(10) Uani 1 1 d U . . H3A H 1.1320 0.3637 1.0770 0.042 Uiso 1 1 calc R . . H3B H 1.2080 0.2683 1.0634 0.042 Uiso 1 1 calc R . . C4 C 0.6309(4) 0.2773(3) 1.0232(2) 0.0194(8) Uani 1 1 d . . . O5 O 0.5751(3) 0.21598(17) 1.07835(16) 0.0210(6) Uani 1 1 d . . . C6 C 0.5992(4) 0.2385(3) 1.1665(2) 0.0209(8) Uani 1 1 d . . . C7 C 0.7568(4) 0.2341(3) 1.2036(2) 0.0208(8) Uani 1 1 d . . . H7A H 0.7934 0.1742 1.1946 0.025 Uiso 1 1 calc R . . H7B H 0.7708 0.2452 1.2653 0.025 Uiso 1 1 calc R . . C8 C 0.8391(4) 0.3026(2) 1.1621(2) 0.0181(8) Uani 1 1 d . . . C9 C 0.5855(4) 0.3718(3) 1.0406(2) 0.0197(8) Uani 1 1 d . . . H9A H 0.6356 0.4144 1.0094 0.024 Uiso 1 1 calc R . . H9B H 0.4820 0.3786 1.0205 0.024 Uiso 1 1 calc R . . C10 C 0.6202(4) 0.3914(3) 1.1347(2) 0.0199(8) Uani 1 1 d . . . O11 O 0.5504(3) 0.32686(17) 1.17834(16) 0.0202(6) Uani 1 1 d . . . O12 O 0.7713(3) 0.38900(16) 1.16333(16) 0.0187(5) Uani 1 1 d . . . C13 C 0.5674(4) 0.2479(3) 0.9349(2) 0.0253(9) Uani 1 1 d . . . H13A H 0.4634 0.2507 0.9274 0.038 Uiso 1 1 calc R . . H13B H 0.5968 0.1869 0.9262 0.038 Uiso 1 1 calc R . . H13C H 0.6006 0.2869 0.8936 0.038 Uiso 1 1 calc R . . C14 C 0.5072(5) 0.1768(3) 1.2075(3) 0.0290(9) Uani 1 1 d . . . H14A H 0.4077 0.1836 1.1801 0.043 Uiso 1 1 calc R . . H14B H 0.5168 0.1911 1.2678 0.043 Uiso 1 1 calc R . . H14C H 0.5375 0.1155 1.2011 0.043 Uiso 1 1 calc R . . C15 C 0.9892(4) 0.3181(3) 1.2093(2) 0.0242(9) Uani 1 1 d . . . H15A H 0.9864 0.3321 1.2686 0.036 Uiso 1 1 calc R . . H15B H 1.0320 0.3676 1.1833 0.036 Uiso 1 1 calc R . . H15C H 1.0462 0.2645 1.2065 0.036 Uiso 1 1 calc R . . C16 C 0.5698(4) 0.4811(3) 1.1586(2) 0.0236(8) Uani 1 1 d . . . H16A H 0.5952 0.4892 1.2200 0.035 Uiso 1 1 calc R . . H16B H 0.4663 0.4850 1.1415 0.035 Uiso 1 1 calc R . . H16C H 0.6152 0.5275 1.1298 0.035 Uiso 1 1 calc R . . O1 O 0.8609(3) 0.16847(17) 1.04280(15) 0.0179(5) Uani 1 1 d . . . C17 C 0.9797(4) 0.1354(2) 1.0106(2) 0.0181(8) Uani 1 1 d . . . C18 C 0.9794(4) 0.1367(2) 0.9233(2) 0.0181(8) Uani 1 1 d . . . C19 C 1.1004(4) 0.1053(2) 0.8950(2) 0.0212(8) Uani 1 1 d . . . H19A H 1.1037 0.1084 0.8363 0.025 Uiso 1 1 calc R . . C20 C 1.2160(4) 0.0696(2) 0.9492(2) 0.0217(8) Uani 1 1 d . . . C21 C 1.2077(4) 0.0646(2) 1.0346(2) 0.0218(8) Uani 1 1 d . . . H21A H 1.2839 0.0381 1.0724 0.026 Uiso 1 1 calc R . . C22 C 1.0913(4) 0.0972(2) 1.0668(2) 0.0202(8) Uani 1 1 d . . . C23 C 0.8524(4) 0.1649(3) 0.8590(2) 0.0233(8) Uani 1 1 d . . . H23A H 0.8728 0.1560 0.8018 0.035 Uiso 1 1 calc R . . H23B H 0.8323 0.2276 0.8672 0.035 Uiso 1 1 calc R . . H23C H 0.7696 0.1292 0.8663 0.035 Uiso 1 1 calc R . . C24 C 1.3420(4) 0.0329(3) 0.9154(3) 0.0284(9) Uani 1 1 d . . . H24A H 1.3283 0.0422 0.8541 0.043 Uiso 1 1 calc R . . H24B H 1.3508 -0.0307 0.9276 0.043 Uiso 1 1 calc R . . H24C H 1.4288 0.0632 0.9426 0.043 Uiso 1 1 calc R . . C25 C 1.0890(4) 0.0887(3) 1.1603(2) 0.0243(9) Uani 1 1 d . . . H25A H 1.0010 0.1146 1.1729 0.036 Uiso 1 1 calc R . . H25B H 1.1709 0.1201 1.1925 0.036 Uiso 1 1 calc R . . H25C H 1.0937 0.0260 1.1762 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.01565(17) 0.01868(18) 0.01647(18) -0.00010(11) 0.00461(12) -0.00062(11) Cl1 0.0261(5) 0.0496(7) 0.0237(5) 0.0146(5) 0.0055(4) 0.0090(5) P1 0.0138(4) 0.0203(5) 0.0123(4) 0.0002(4) 0.0021(3) -0.0003(4) C1 0.0275(12) 0.0292(12) 0.0286(12) 0.0000(9) 0.0081(9) -0.0020(9) C2 0.0587(18) 0.0613(18) 0.0618(18) 0.0007(10) 0.0114(10) 0.0001(10) C3 0.0318(13) 0.0382(13) 0.0356(13) 0.0017(9) 0.0059(9) 0.0000(9) C4 0.0173(18) 0.027(2) 0.0148(18) 0.0018(16) 0.0043(14) -0.0011(16) O5 0.0219(13) 0.0248(14) 0.0175(13) -0.0022(11) 0.0066(11) -0.0071(11) C6 0.026(2) 0.0222(19) 0.0165(19) 0.0004(16) 0.0085(16) -0.0001(16) C7 0.028(2) 0.024(2) 0.0110(17) 0.0011(16) 0.0054(15) 0.0021(16) C8 0.0200(18) 0.0204(18) 0.0140(18) -0.0020(15) 0.0030(14) 0.0030(15) C9 0.0148(18) 0.029(2) 0.0150(18) 0.0033(16) 0.0024(14) 0.0021(16) C10 0.0183(18) 0.024(2) 0.0174(19) 0.0028(16) 0.0040(15) -0.0007(16) O11 0.0215(14) 0.0222(14) 0.0191(13) 0.0026(11) 0.0094(11) 0.0001(11) O12 0.0189(13) 0.0190(13) 0.0178(13) -0.0004(11) 0.0022(10) 0.0018(11) C13 0.0180(19) 0.039(2) 0.019(2) -0.0047(18) 0.0031(16) -0.0039(17) C14 0.033(2) 0.030(2) 0.026(2) 0.0017(18) 0.0131(18) -0.0048(19) C15 0.024(2) 0.029(2) 0.0184(19) -0.0037(17) -0.0011(16) 0.0013(17) C16 0.027(2) 0.023(2) 0.021(2) 0.0026(17) 0.0072(16) 0.0028(17) O1 0.0191(13) 0.0194(13) 0.0159(13) -0.0009(11) 0.0047(10) -0.0002(11) C17 0.0193(19) 0.0182(19) 0.0175(19) -0.0003(15) 0.0050(15) -0.0022(15) C18 0.024(2) 0.0143(18) 0.0159(19) -0.0004(14) 0.0037(15) -0.0014(14) C19 0.025(2) 0.0196(19) 0.020(2) -0.0021(16) 0.0055(16) -0.0051(16) C20 0.022(2) 0.0160(18) 0.028(2) -0.0021(16) 0.0077(16) -0.0047(15) C21 0.0216(19) 0.0190(19) 0.024(2) 0.0014(16) 0.0013(16) -0.0010(16) C22 0.024(2) 0.0131(18) 0.024(2) 0.0013(16) 0.0051(16) -0.0032(15) C23 0.024(2) 0.027(2) 0.0188(19) 0.0002(17) 0.0030(16) 0.0020(17) C24 0.026(2) 0.029(2) 0.032(2) 0.0009(19) 0.0087(18) 0.0024(18) C25 0.032(2) 0.022(2) 0.018(2) 0.0038(16) 0.0019(17) 0.0038(17) _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 C2 2.124(6) . ? Pd1 C3 2.142(4) . ? Pd1 C1 2.189(4) . ? Pd1 P1 2.2931(10) . ? Pd1 Cl1 2.3586(11) . ? P1 O1 1.642(3) . ? P1 C4 1.875(4) . ? P1 C8 1.881(4) . ? C1 C2 1.312(7) . ? C1 H1A 0.9500 . ? C1 H1B 0.9500 . ? C2 C3 1.387(8) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C3 H3B 0.9500 . ? C4 O5 1.446(4) . ? C4 C13 1.506(5) . ? C4 C9 1.529(5) . ? O5 C6 1.434(4) . ? C6 O11 1.436(5) . ? C6 C14 1.508(5) . ? C6 C7 1.519(5) . ? C7 C8 1.521(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O12 1.458(4) . ? C8 C15 1.517(5) . ? C9 C10 1.516(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O11 1.432(4) . ? C10 O12 1.436(4) . ? C10 C16 1.509(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? O1 C17 1.418(4) . ? C17 C22 1.394(5) . ? C17 C18 1.400(6) . ? C18 C19 1.396(5) . ? C18 C23 1.509(5) . ? C19 C20 1.388(5) . ? C19 H19A 0.9500 . ? C20 C21 1.386(6) . ? C20 C24 1.510(5) . ? C21 C22 1.396(5) . ? C21 H21A 0.9500 . ? C22 C25 1.509(5) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 C2 Pd1 C3 38.0(2) . . ? C2 Pd1 C1 35.38(19) . . ? C3 Pd1 C1 67.28(17) . . ? C2 Pd1 P1 131.86(17) . . ? C3 Pd1 P1 99.15(13) . . ? C1 Pd1 P1 166.39(11) . . ? C2 Pd1 Cl1 123.68(17) . . ? C3 Pd1 Cl1 160.43(13) . . ? C1 Pd1 Cl1 93.16(11) . . ? P1 Pd1 Cl1 100.39(4) . . ? O1 P1 C4 100.99(15) . . ? O1 P1 C8 106.07(15) . . ? C4 P1 C8 93.68(16) . . ? O1 P1 Pd1 113.74(10) . . ? C4 P1 Pd1 122.72(12) . . ? C8 P1 Pd1 116.62(13) . . ? C2 C1 Pd1 69.6(3) . . ? C2 C1 H1A 120.0 . . ? Pd1 C1 H1A 72.3 . . ? C2 C1 H1B 120.0 . . ? Pd1 C1 H1B 130.7 . . ? H1A C1 H1B 120.0 . . ? C1 C2 C3 125.5(6) . . ? C1 C2 Pd1 75.0(3) . . ? C3 C2 Pd1 71.7(3) . . ? C1 C2 H2A 117.3 . . ? C3 C2 H2A 117.3 . . ? Pd1 C2 H2A 128.6 . . ? C2 C3 Pd1 70.3(3) . . ? C2 C3 H3A 120.0 . . ? Pd1 C3 H3A 72.8 . . ? C2 C3 H3B 120.0 . . ? Pd1 C3 H3B 129.2 . . ? H3A C3 H3B 120.0 . . ? O5 C4 C13 104.8(3) . . ? O5 C4 C9 109.8(3) . . ? C13 C4 C9 111.5(3) . . ? O5 C4 P1 109.6(2) . . ? C13 C4 P1 114.3(3) . . ? C9 C4 P1 106.8(3) . . ? C6 O5 C4 116.0(3) . . ? O5 C6 O11 110.5(3) . . ? O5 C6 C14 106.1(3) . . ? O11 C6 C14 106.8(3) . . ? O5 C6 C7 110.6(3) . . ? O11 C6 C7 108.1(3) . . ? C14 C6 C7 114.6(3) . . ? C6 C7 C8 110.6(3) . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? O12 C8 C15 103.8(3) . . ? O12 C8 C7 109.6(3) . . ? C15 C8 C7 113.7(3) . . ? O12 C8 P1 105.5(2) . . ? C15 C8 P1 113.6(3) . . ? C7 C8 P1 110.1(2) . . ? C10 C9 C4 110.2(3) . . ? C10 C9 H9A 109.6 . . ? C4 C9 H9A 109.6 . . ? C10 C9 H9B 109.6 . . ? C4 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? O11 C10 O12 110.8(3) . . ? O11 C10 C16 106.8(3) . . ? O12 C10 C16 106.8(3) . . ? O11 C10 C9 108.3(3) . . ? O12 C10 C9 110.2(3) . . ? C16 C10 C9 113.9(3) . . ? C10 O11 C6 112.2(3) . . ? C10 O12 C8 116.3(3) . . ? C4 C13 H13A 109.5 . . ? C4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 C14 H14A 109.5 . . ? C6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C17 O1 P1 121.3(2) . . ? C22 C17 C18 121.3(4) . . ? C22 C17 O1 118.7(3) . . ? C18 C17 O1 119.9(3) . . ? C19 C18 C17 117.6(3) . . ? C19 C18 C23 119.1(3) . . ? C17 C18 C23 123.2(4) . . ? C20 C19 C18 122.8(4) . . ? C20 C19 H19A 118.6 . . ? C18 C19 H19A 118.6 . . ? C19 C20 C21 117.5(4) . . ? C19 C20 C24 120.9(4) . . ? C21 C20 C24 121.5(4) . . ? C20 C21 C22 122.3(4) . . ? C20 C21 H21A 118.8 . . ? C22 C21 H21A 118.8 . . ? C17 C22 C21 118.3(3) . . ? C17 C22 C25 122.3(4) . . ? C21 C22 C25 119.4(3) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C2 Pd1 P1 O1 -38.9(3) . . . . ? C3 Pd1 P1 O1 -60.75(17) . . . . ? C1 Pd1 P1 O1 -56.7(5) . . . . ? Cl1 Pd1 P1 O1 118.25(11) . . . . ? C2 Pd1 P1 C4 -160.9(3) . . . . ? C3 Pd1 P1 C4 177.25(19) . . . . ? C1 Pd1 P1 C4 -178.7(5) . . . . ? Cl1 Pd1 P1 C4 -3.76(15) . . . . ? C2 Pd1 P1 C8 85.1(3) . . . . ? C3 Pd1 P1 C8 63.21(18) . . . . ? C1 Pd1 P1 C8 67.3(5) . . . . ? Cl1 Pd1 P1 C8 -117.79(13) . . . . ? C3 Pd1 C1 C2 27.5(3) . . . . ? P1 Pd1 C1 C2 23.2(7) . . . . ? Cl1 Pd1 C1 C2 -151.8(3) . . . . ? Pd1 C1 C2 C3 -53.9(5) . . . . ? C3 Pd1 C2 C1 -136.1(5) . . . . ? P1 Pd1 C2 C1 -172.9(2) . . . . ? Cl1 Pd1 C2 C1 34.5(4) . . . . ? C1 Pd1 C2 C3 136.1(5) . . . . ? P1 Pd1 C2 C3 -36.7(4) . . . . ? Cl1 Pd1 C2 C3 170.6(2) . . . . ? C1 C2 C3 Pd1 55.3(5) . . . . ? C1 Pd1 C3 C2 -25.8(3) . . . . ? P1 Pd1 C3 C2 153.2(3) . . . . ? Cl1 Pd1 C3 C2 -23.9(6) . . . . ? O1 P1 C4 O5 51.0(3) . . . . ? C8 P1 C4 O5 -56.1(3) . . . . ? Pd1 P1 C4 O5 178.79(17) . . . . ? O1 P1 C4 C13 -66.3(3) . . . . ? C8 P1 C4 C13 -173.4(3) . . . . ? Pd1 P1 C4 C13 61.5(3) . . . . ? O1 P1 C4 C9 169.9(2) . . . . ? C8 P1 C4 C9 62.8(3) . . . . ? Pd1 P1 C4 C9 -62.3(3) . . . . ? C13 C4 O5 C6 -169.4(3) . . . . ? C9 C4 O5 C6 -49.5(4) . . . . ? P1 C4 O5 C6 67.5(3) . . . . ? C4 O5 C6 O11 53.1(4) . . . . ? C4 O5 C6 C14 168.6(3) . . . . ? C4 O5 C6 C7 -66.6(4) . . . . ? O5 C6 C7 C8 63.7(4) . . . . ? O11 C6 C7 C8 -57.5(4) . . . . ? C14 C6 C7 C8 -176.5(3) . . . . ? C6 C7 C8 O12 50.2(4) . . . . ? C6 C7 C8 C15 165.9(3) . . . . ? C6 C7 C8 P1 -65.4(3) . . . . ? O1 P1 C8 O12 -163.5(2) . . . . ? C4 P1 C8 O12 -60.9(2) . . . . ? Pd1 P1 C8 O12 68.7(2) . . . . ? O1 P1 C8 C15 83.5(3) . . . . ? C4 P1 C8 C15 -173.9(3) . . . . ? Pd1 P1 C8 C15 -44.3(3) . . . . ? O1 P1 C8 C7 -45.3(3) . . . . ? C4 P1 C8 C7 57.3(3) . . . . ? Pd1 P1 C8 C7 -173.1(2) . . . . ? O5 C4 C9 C10 50.6(4) . . . . ? C13 C4 C9 C10 166.3(3) . . . . ? P1 C4 C9 C10 -68.1(3) . . . . ? C4 C9 C10 O11 -57.3(4) . . . . ? C4 C9 C10 O12 64.0(4) . . . . ? C4 C9 C10 C16 -175.9(3) . . . . ? O12 C10 O11 C6 -58.9(4) . . . . ? C16 C10 O11 C6 -174.9(3) . . . . ? C9 C10 O11 C6 62.0(4) . . . . ? O5 C6 O11 C10 -59.1(4) . . . . ? C14 C6 O11 C10 -174.1(3) . . . . ? C7 C6 O11 C10 62.1(4) . . . . ? O11 C10 O12 C8 52.3(4) . . . . ? C16 C10 O12 C8 168.3(3) . . . . ? C9 C10 O12 C8 -67.5(4) . . . . ? C15 C8 O12 C10 -170.3(3) . . . . ? C7 C8 O12 C10 -48.5(4) . . . . ? P1 C8 O12 C10 69.9(3) . . . . ? C4 P1 O1 C17 144.5(3) . . . . ? C8 P1 O1 C17 -118.4(3) . . . . ? Pd1 P1 O1 C17 11.1(3) . . . . ? P1 O1 C17 C22 109.7(3) . . . . ? P1 O1 C17 C18 -74.1(4) . . . . ? C22 C17 C18 C19 -5.4(5) . . . . ? O1 C17 C18 C19 178.5(3) . . . . ? C22 C17 C18 C23 170.7(3) . . . . ? O1 C17 C18 C23 -5.3(5) . . . . ? C17 C18 C19 C20 3.1(5) . . . . ? C23 C18 C19 C20 -173.2(3) . . . . ? C18 C19 C20 C21 0.9(6) . . . . ? C18 C19 C20 C24 177.4(3) . . . . ? C19 C20 C21 C22 -2.7(6) . . . . ? C24 C20 C21 C22 -179.2(4) . . . . ? C18 C17 C22 C21 3.7(5) . . . . ? O1 C17 C22 C21 179.8(3) . . . . ? C18 C17 C22 C25 -175.2(3) . . . . ? O1 C17 C22 C25 0.9(5) . . . . ? C20 C21 C22 C17 0.4(6) . . . . ? C20 C21 C22 C25 179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.645 _refine_diff_density_min -0.771 _refine_diff_density_rms 0.110