# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/2120 # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_complex2 _publ_section_title ; Allyl, Olefin Aryl and Alkyl-organometallic Duphos-complexes of Palladium. ; _publ_contact_author ; Drago Daniela Laboratory of Inorganic Chemistry, Universit\"atstr. 6 CH-8092 Z\"urich, Switzerland ; _publ_contact_author_email 'drago@inorg.chem.ethz.ch' _publ_contact_author_fax '41(1)6321090' _publ_contact_author_phone '41(1)6324459' _publ_requested_journal 'Dalton' _publ_contact_letter ; ; loop_ _publ_author_name _publ_author_address 'Drago Daniela' ; Laboratory of Inorganic Chemistry, Universit\"atstr. 6 CH-8092 Z\"urich, Switzerland ; 'Pregosin, Paul S.' ; Laboratory of Inorganic Chemistry, Universit\"atstr. 6 CH-8092 Z\"urich, Switzerland ; _publ_section_abstract ; A series of organometallic chiral complexes of palladium containing the chelate Duphos, 1, (1+1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene) have been prepared. These include the 1,3-diphenyl allyl cationic compound, [Pd(PhCHCHCHPh)(1)](CF3SO3), 2, the Pd(0) fumaronitrile, complex Pd(NCCH=CHCN)(1), 3, and the penta-fluoro phenyl derivatives Pd(R)(C6F5)(1), 4a-c, R=Me, Et, n-Bu, respectively. The solid state structures of 2 and 4a have been determined by X-ray diffraction. The structure of complex 4a deviates markedly from the expected square planar geometry. Duphos 1 affords a ca 98% ee in the enantioselective allylic alkylation reaction of a 1,3-diphenyl allyl precursor. Detailed 1H and 13CNMR results are reported. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H43 Cl2 F3 O3 P2 Pd S' _chemical_formula_weight 839.99 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' 'F' 'F' 0.0171 0.0103 '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' 'S' 'S' 0.1246 0.1234 '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' 'Cl' 'Cl' 0.1484 0.1585 '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)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.0798(3) _cell_length_b 11.4320(3) _cell_length_c 13.2985(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.3940(10) _cell_angle_gamma 90.00 _cell_volume 1907.66(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6112 _cell_measurement_theta_min 3 _cell_measurement_theta_max 32.89 _exptl_crystal_description 'plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 0.812 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; 'Program Sadabs, G. Sheldrick, 1997, G\"ottingen' ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Four circle diffractometer Syntex P21 Graphite monochromator' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 150 _diffrn_standards_decay_% . _diffrn_reflns_number 19700 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.1688 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 32.89 _reflns_number_total 12152 _reflns_number_gt 5410 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0370P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0007(4) _refine_ls_number_reflns 12152 _refine_ls_number_parameters 425 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1441 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 0.822 _refine_ls_restrained_S_all 0.822 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.002 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 0.72292(3) 0.14530(4) 0.85392(3) 0.04450(12) Uani 1 1 d . . . P1 P 0.84022(11) 0.01791(12) 0.81373(11) 0.0435(3) Uani 1 1 d . . . C1L C 0.5923(5) 0.2349(6) 0.9026(5) 0.0639(17) Uani 1 1 d . . . H1LA H 0.5269 0.1881 0.8815 0.077 Uiso 1 1 calc R . . C1 C 1.0573(5) 0.0765(6) 0.9120(5) 0.0705(18) Uani 1 1 d . . . H1A H 1.1204 0.0568 0.9667 0.106 Uiso 1 1 calc R . . H1B H 1.0359 0.1548 0.9224 0.106 Uiso 1 1 calc R . . H1C H 1.0718 0.0711 0.8453 0.106 Uiso 1 1 calc R . . S1 S 0.75135(17) -0.5634(3) 1.28244(18) 0.0979(7) Uani 1 1 d . . . O1 O 0.7812(5) -0.6425(6) 1.2190(6) 0.143(3) Uani 1 1 d . . . F1 F 0.6036(7) -0.6877(7) 1.3047(5) 0.210(4) Uani 1 1 d . . . C1' C 0.6145(7) -0.5717(12) 1.2571(7) 0.126(4) Uani 1 1 d . . . C1M C 0.1975(9) 0.2336(11) 0.5350(8) 0.154(4) Uani 1 1 d . . . H1MA H 0.2288 0.1724 0.5847 0.185 Uiso 1 1 calc R . . H1MB H 0.1405 0.2688 0.5582 0.185 Uiso 1 1 calc R . . Cl1 Cl 0.1434(2) 0.1710(2) 0.4178(2) 0.1297(9) Uani 1 1 d . . . C2L C 0.6660(5) 0.1830(5) 0.9904(5) 0.0534(17) Uani 1 1 d . . . H2LA H 0.7087 0.2330 1.0465 0.064 Uiso 1 1 calc R . . C2 C 0.9683(5) -0.0082(5) 0.9148(4) 0.0546(15) Uani 1 1 d . . . H2A H 0.9546 0.0017 0.9830 0.066 Uiso 1 1 calc R . . P2 P 0.72320(11) 0.24290(12) 0.70454(11) 0.0432(3) Uani 1 1 d . . . O2 O 0.7948(4) -0.5648(5) 1.3917(5) 0.113(2) Uani 1 1 d . . . F2 F 0.5734(4) -0.5006(6) 1.3087(5) 0.152(2) Uani 1 1 d . . . Cl2 Cl 0.2914(2) 0.3367(4) 0.5407(3) 0.1849(16) Uani 1 1 d . . . C3L C 0.6874(5) 0.0639(6) 0.9919(5) 0.0529(17) Uani 1 1 d . . . H3LA H 0.6210 0.0190 0.9702 0.063 Uiso 1 1 calc R . . C3 C 0.9917(5) -0.1388(6) 0.9041(5) 0.0685(18) Uani 1 1 d . . . H3A H 1.0248 -0.1506 0.8482 0.082 Uiso 1 1 calc R . . H3B H 1.0393 -0.1682 0.9689 0.082 Uiso 1 1 calc R . . O3 O 0.7457(8) -0.4379(6) 1.2375(6) 0.184(4) Uani 1 1 d . . . F3 F 0.5585(4) -0.5823(6) 1.1613(4) 0.144(3) Uani 1 1 d . . . C4 C 0.8863(6) -0.2012(5) 0.8795(5) 0.077(2) Uani 1 1 d . . . H4A H 0.8596 -0.2014 0.9406 0.092 Uiso 1 1 calc R . . H4B H 0.8945 -0.2816 0.8599 0.092 Uiso 1 1 calc R . . C4L C 0.7656(5) 0.0044(5) 1.0785(5) 0.0543(14) Uani 1 1 d . . . C5 C 0.8082(6) -0.1366(6) 0.7885(6) 0.064(2) Uani 1 1 d . . . H5A H 0.8263 -0.1577 0.7242 0.077 Uiso 1 1 calc R . . C5L C 0.7517(6) -0.1150(6) 1.0943(6) 0.0702(18) Uani 1 1 d . . . H5LA H 0.6965 -0.1555 1.0480 0.084 Uiso 1 1 calc R . . C6 C 0.6894(5) -0.1693(7) 0.7724(6) 0.086(2) Uani 1 1 d . . . H6A H 0.6800 -0.2518 0.7598 0.128 Uiso 1 1 calc R . . H6B H 0.6457 -0.1271 0.7134 0.128 Uiso 1 1 calc R . . H6C H 0.6689 -0.1492 0.8342 0.128 Uiso 1 1 calc R . . C6L C 0.8197(8) -0.1731(8) 1.1785(7) 0.097(3) Uani 1 1 d . . . H6LA H 0.8079 -0.2513 1.1907 0.116 Uiso 1 1 calc R . . C7 C 0.8661(4) 0.0693(5) 0.6932(4) 0.0459(13) Uani 1 1 d . . . C7L C 0.9059(8) -0.1138(11) 1.2447(7) 0.112(3) Uani 1 1 d . . . H7LA H 0.9551 -0.1540 1.2976 0.135 Uiso 1 1 calc R . . C8 C 0.9382(4) 0.0121(6) 0.6496(4) 0.0575(15) Uani 1 1 d . . . H8A H 0.9755 -0.0526 0.6835 0.069 Uiso 1 1 calc R . . C8L C 0.9177(6) 0.0031(9) 1.2317(7) 0.100(3) Uani 1 1 d . . . H8LA H 0.9727 0.0438 1.2782 0.120 Uiso 1 1 calc R . . C9 C 0.9545(5) 0.0506(6) 0.5571(5) 0.0701(18) Uani 1 1 d . . . H9A H 1.0022 0.0120 0.5283 0.084 Uiso 1 1 calc R . . C9L C 0.8473(5) 0.0618(7) 1.1485(5) 0.0724(19) Uani 1 1 d . . . H9LA H 0.8560 0.1416 1.1404 0.087 Uiso 1 1 calc R . . C10 C 0.8983(4) 0.1485(9) 0.5070(4) 0.0716(16) Uani 1 1 d . . . H10A H 0.9088 0.1758 0.4448 0.086 Uiso 1 1 calc R . . C10L C 0.5661(5) 0.3596(6) 0.8942(5) 0.0608(17) Uani 1 1 d . . . C11 C 0.8287(5) 0.2033(6) 0.5492(5) 0.0660(17) Uani 1 1 d . . . H11A H 0.7905 0.2671 0.5144 0.079 Uiso 1 1 calc R . . C11L C 0.6268(6) 0.4470(6) 0.9566(6) 0.077(2) Uani 1 1 d . . . H11B H 0.6886 0.4270 1.0083 0.092 Uiso 1 1 calc R . . C12 C 0.8124(4) 0.1670(5) 0.6434(4) 0.0447(15) Uani 1 1 d . . . C12L C 0.5963(9) 0.5624(7) 0.9425(8) 0.106(3) Uani 1 1 d . . . H12A H 0.6373 0.6197 0.9851 0.128 Uiso 1 1 calc R . . C13L C 0.5070(10) 0.5931(9) 0.8672(10) 0.120(4) Uani 1 1 d . . . H13A H 0.4879 0.6717 0.8589 0.145 Uiso 1 1 calc R . . C13 C 0.5605(5) 0.1625(9) 0.5249(5) 0.099(3) Uani 1 1 d . . . H13B H 0.4916 0.1787 0.4777 0.148 Uiso 1 1 calc R . . H13C H 0.5583 0.0894 0.5598 0.148 Uiso 1 1 calc R . . H13D H 0.6122 0.1580 0.4863 0.148 Uiso 1 1 calc R . . C14 C 0.5916(4) 0.2615(6) 0.6071(5) 0.0570(15) Uani 1 1 d . . . H14A H 0.5383 0.2612 0.6463 0.068 Uiso 1 1 calc R . . C14L C 0.4442(8) 0.5128(10) 0.8033(8) 0.105(3) Uani 1 1 d . . . H14B H 0.3839 0.5365 0.7515 0.126 Uiso 1 1 calc R . . C15 C 0.5934(5) 0.3852(6) 0.5647(5) 0.0723(19) Uani 1 1 d . . . H15A H 0.6265 0.3854 0.5081 0.087 Uiso 1 1 calc R . . H15B H 0.5213 0.4151 0.5382 0.087 Uiso 1 1 calc R . . C15L C 0.4713(6) 0.3928(7) 0.8162(7) 0.082(2) Uani 1 1 d . . . H15C H 0.4280 0.3365 0.7745 0.099 Uiso 1 1 calc R . . C16 C 0.6570(5) 0.4608(5) 0.6550(6) 0.073(2) Uani 1 1 d . . . H16A H 0.6700 0.5372 0.6293 0.087 Uiso 1 1 calc R . . H16B H 0.6179 0.4712 0.7064 0.087 Uiso 1 1 calc R . . C17 C 0.7618(5) 0.3991(5) 0.7042(5) 0.0543(14) Uani 1 1 d . . . H17A H 0.8072 0.4078 0.6573 0.065 Uiso 1 1 calc R . . C18 C 0.8226(7) 0.4430(7) 0.8113(7) 0.083(3) Uani 1 1 d . . . H18A H 0.8406 0.5239 0.8066 0.125 Uiso 1 1 calc R . . H18B H 0.8866 0.3981 0.8371 0.125 Uiso 1 1 calc R . . H18C H 0.7792 0.4351 0.8584 0.125 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 0.0576(2) 0.0413(2) 0.03933(18) 0.0040(3) 0.02137(15) 0.0052(3) P1 0.0585(9) 0.0370(8) 0.0381(7) 0.0009(6) 0.0189(7) 0.0039(6) C1L 0.065(4) 0.071(4) 0.072(4) 0.013(4) 0.047(3) 0.014(3) C1 0.072(4) 0.077(5) 0.059(4) -0.011(3) 0.013(3) -0.006(3) S1 0.0894(14) 0.134(2) 0.0679(14) -0.0019(14) 0.0185(12) 0.0015(14) O1 0.114(5) 0.130(6) 0.175(7) -0.051(6) 0.026(4) 0.033(4) F1 0.318(10) 0.180(7) 0.111(5) 0.024(5) 0.027(5) -0.152(7) C1' 0.080(6) 0.224(14) 0.063(6) -0.043(7) 0.002(5) 0.030(7) C1M 0.213(12) 0.153(10) 0.111(9) 0.008(8) 0.070(9) -0.015(9) Cl1 0.180(2) 0.121(3) 0.1085(16) 0.0077(17) 0.0755(16) -0.0323(18) C2L 0.068(4) 0.051(4) 0.049(3) 0.000(3) 0.030(3) 0.003(3) C2 0.077(4) 0.047(3) 0.042(3) 0.003(3) 0.020(3) 0.012(3) P2 0.0523(8) 0.0402(8) 0.0380(7) 0.0035(6) 0.0141(6) 0.0029(6) O2 0.106(4) 0.117(5) 0.093(4) 0.009(4) -0.009(3) -0.041(4) F2 0.138(4) 0.201(7) 0.135(5) -0.013(5) 0.069(4) 0.026(4) Cl2 0.123(2) 0.229(4) 0.171(3) 0.033(3) -0.010(2) -0.041(3) C3L 0.056(4) 0.056(4) 0.054(4) 0.006(3) 0.026(3) -0.006(3) C3 0.081(5) 0.056(4) 0.069(4) 0.015(3) 0.022(4) 0.019(4) O3 0.327(11) 0.100(5) 0.141(6) 0.024(5) 0.090(7) -0.089(6) F3 0.102(4) 0.250(8) 0.069(3) 0.026(4) 0.004(3) -0.028(4) C4 0.126(6) 0.034(3) 0.071(5) 0.004(3) 0.031(4) 0.019(4) C4L 0.073(4) 0.051(4) 0.049(3) 0.010(3) 0.033(3) 0.009(3) C5 0.090(5) 0.047(4) 0.066(5) -0.014(4) 0.041(4) -0.011(4) C5L 0.097(5) 0.061(4) 0.067(4) 0.014(4) 0.048(4) 0.013(4) C6 0.096(5) 0.067(5) 0.105(6) -0.021(4) 0.046(5) -0.030(4) C6L 0.142(8) 0.070(5) 0.100(6) 0.055(5) 0.071(6) 0.047(5) C7 0.056(3) 0.047(3) 0.039(3) -0.006(3) 0.019(3) 0.002(3) C7L 0.114(7) 0.155(10) 0.077(6) 0.051(7) 0.042(5) 0.054(7) C8 0.070(4) 0.060(4) 0.046(3) 0.007(3) 0.021(3) 0.018(3) C8L 0.103(6) 0.122(8) 0.071(5) 0.016(6) 0.018(5) 0.026(6) C9 0.085(4) 0.087(5) 0.054(4) 0.008(4) 0.046(3) 0.021(4) C9L 0.084(5) 0.077(5) 0.062(4) -0.002(4) 0.030(4) 0.005(4) C10 0.097(4) 0.083(4) 0.048(3) 0.014(5) 0.043(3) 0.008(6) C10L 0.073(4) 0.059(4) 0.066(4) 0.021(3) 0.046(4) 0.022(3) C11 0.088(4) 0.063(4) 0.049(4) 0.019(3) 0.021(3) 0.017(3) C11L 0.109(6) 0.060(4) 0.077(5) 0.011(4) 0.052(4) 0.020(4) C12 0.054(3) 0.046(5) 0.035(2) 0.000(3) 0.014(2) 0.000(3) C12L 0.161(8) 0.063(5) 0.121(8) 0.011(5) 0.083(7) 0.023(6) C13L 0.171(11) 0.086(7) 0.145(10) 0.055(7) 0.110(9) 0.063(7) C13 0.088(4) 0.116(7) 0.077(4) -0.033(6) -0.002(4) -0.008(6) C14 0.054(3) 0.062(4) 0.054(4) 0.001(3) 0.013(3) -0.002(3) C14L 0.106(7) 0.123(8) 0.109(8) 0.052(7) 0.066(6) 0.062(6) C15 0.070(4) 0.082(5) 0.062(4) 0.016(4) 0.013(3) 0.020(4) C15L 0.080(5) 0.085(6) 0.099(6) 0.023(5) 0.054(5) 0.031(4) C16 0.084(5) 0.045(4) 0.096(6) 0.022(4) 0.037(4) 0.008(3) C17 0.071(4) 0.044(3) 0.053(4) -0.002(3) 0.025(3) -0.005(3) C18 0.100(6) 0.072(5) 0.084(6) -0.026(5) 0.037(5) -0.033(4) _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 C2L 2.190(6) . ? Pd1 C3L 2.221(6) . ? Pd1 C1L 2.238(5) . ? Pd1 P2 2.2794(14) . ? Pd1 P1 2.2855(14) . ? P1 C7 1.826(5) . ? P1 C5 1.825(7) . ? P1 C2 1.852(6) . ? C1L C2L 1.417(9) . ? C1L C10L 1.464(9) . ? C1 C2 1.523(8) . ? S1 O1 1.366(6) . ? S1 O2 1.403(6) . ? S1 O3 1.548(7) . ? S1 C1' 1.728(9) . ? F1 C1' 1.494(14) . ? C1' F2 1.277(10) . ? C1' F3 1.283(9) . ? C1M Cl1 1.680(11) . ? C1M Cl2 1.688(11) . ? C2L C3L 1.389(8) . ? C2 C3 1.539(8) . ? P2 C12 1.819(5) . ? P2 C14 1.851(6) . ? P2 C17 1.855(6) . ? C3L C4L 1.473(8) . ? C3 C4 1.503(9) . ? C4 C5 1.535(9) . ? C4L C9L 1.370(9) . ? C4L C5L 1.400(9) . ? C5 C6 1.553(9) . ? C5L C6L 1.387(11) . ? C6L C7L 1.394(13) . ? C7 C12 1.384(7) . ? C7 C8 1.401(7) . ? C7L C8L 1.363(13) . ? C8 C9 1.379(8) . ? C8L C9L 1.395(10) . ? C9 C10 1.400(10) . ? C10 C11 1.351(8) . ? C10L C11L 1.394(10) . ? C10L C15L 1.425(10) . ? C11 C12 1.392(7) . ? C11L C12L 1.376(10) . ? C12L C13L 1.353(13) . ? C13L C14L 1.358(13) . ? C13 C14 1.546(10) . ? C14 C15 1.525(9) . ? C14L C15L 1.415(12) . ? C15 C16 1.522(9) . ? C16 C17 1.515(8) . ? C17 C18 1.509(9) . ? 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 C2L Pd1 C3L 36.7(2) . . ? C2L Pd1 C1L 37.3(2) . . ? C3L Pd1 C1L 66.3(2) . . ? C2L Pd1 P2 135.27(17) . . ? C3L Pd1 P2 167.85(17) . . ? C1L Pd1 P2 102.55(17) . . ? C2L Pd1 P1 136.63(17) . . ? C3L Pd1 P1 103.71(17) . . ? C1L Pd1 P1 167.60(18) . . ? P2 Pd1 P1 86.66(5) . . ? C7 P1 C5 103.9(3) . . ? C7 P1 C2 109.6(3) . . ? C5 P1 C2 95.2(3) . . ? C7 P1 Pd1 107.63(18) . . ? C5 P1 Pd1 121.7(2) . . ? C2 P1 Pd1 117.53(19) . . ? C2L C1L C10L 124.1(7) . . ? C2L C1L Pd1 69.5(3) . . ? C10L C1L Pd1 127.2(4) . . ? O1 S1 O2 121.9(5) . . ? O1 S1 O3 111.5(5) . . ? O2 S1 O3 111.9(4) . . ? O1 S1 C1' 107.7(5) . . ? O2 S1 C1' 107.2(4) . . ? O3 S1 C1' 92.4(6) . . ? F2 C1' F3 112.6(9) . . ? F2 C1' F1 103.4(9) . . ? F3 C1' F1 103.9(9) . . ? F2 C1' S1 115.5(8) . . ? F3 C1' S1 118.0(7) . . ? F1 C1' S1 100.6(7) . . ? Cl1 C1M Cl2 116.7(6) . . ? C3L C2L C1L 120.7(7) . . ? C3L C2L Pd1 72.8(4) . . ? C1L C2L Pd1 73.2(3) . . ? C1 C2 C3 116.2(5) . . ? C1 C2 P1 114.9(4) . . ? C3 C2 P1 104.6(4) . . ? C12 P2 C14 109.2(3) . . ? C12 P2 C17 104.4(3) . . ? C14 P2 C17 95.0(3) . . ? C12 P2 Pd1 108.34(18) . . ? C14 P2 Pd1 115.8(2) . . ? C17 P2 Pd1 122.7(2) . . ? C2L C3L C4L 123.8(7) . . ? C2L C3L Pd1 70.4(4) . . ? C4L C3L Pd1 125.3(4) . . ? C4 C3 C2 106.6(5) . . ? C3 C4 C5 108.0(5) . . ? C9L C4L C5L 118.3(6) . . ? C9L C4L C3L 123.1(6) . . ? C5L C4L C3L 118.4(6) . . ? C4 C5 C6 114.3(6) . . ? C4 C5 P1 104.7(5) . . ? C6 C5 P1 115.3(5) . . ? C6L C5L C4L 120.5(8) . . ? C5L C6L C7L 119.8(8) . . ? C12 C7 C8 119.2(5) . . ? C12 C7 P1 119.0(4) . . ? C8 C7 P1 121.8(4) . . ? C8L C7L C6L 119.8(8) . . ? C9 C8 C7 120.8(6) . . ? C7L C8L C9L 120.0(9) . . ? C8 C9 C10 119.1(5) . . ? C4L C9L C8L 121.5(8) . . ? C11 C10 C9 119.9(5) . . ? C11L C10L C15L 118.3(7) . . ? C11L C10L C1L 124.8(6) . . ? C15L C10L C1L 116.9(7) . . ? C10 C11 C12 121.9(6) . . ? C12L C11L C10L 120.8(8) . . ? C7 C12 C11 119.0(5) . . ? C7 C12 P2 118.3(4) . . ? C11 C12 P2 122.7(5) . . ? C13L C12L C11L 120.4(10) . . ? C12L C13L C14L 122.0(9) . . ? C15 C14 C13 116.5(6) . . ? C15 C14 P2 104.9(4) . . ? C13 C14 P2 114.7(5) . . ? C13L C14L C15L 119.6(9) . . ? C16 C15 C14 107.3(5) . . ? C14L C15L C10L 118.9(9) . . ? C17 C16 C15 107.6(5) . . ? C18 C17 C16 115.1(6) . . ? C18 C17 P2 112.9(5) . . ? C16 C17 P2 103.6(4) . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 32.89 _diffrn_measured_fraction_theta_full 0.912 _refine_diff_density_max 0.836 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.071 # ---end-of-data-block--- #============================================================================ # 1. SUBMISSION DETAILS #===END # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_complex4a _publ_contact_author ; Drago Daniela Laboratory of Inorganic Chemistry, Universit\"atstr. 6 CH-8092 Z\"urich, Switzerland ; _publ_contact_author_email 'drago@inorg.chem.ethz.ch' _publ_contact_author_fax '41(1)6321090' _publ_contact_author_phone '41(1)6324459' _publ_requested_journal 'Dalton' _publ_contact_letter ; ; _publ_section_title ; Allyl, Olefin Aryl and Alkyl-organometallic Duphos-complexes of Palladium. ; loop_ _publ_author_name _publ_author_address 'Drago Daniela' ; Laboratory of Inorganic Chemistry, Universit\"atstr. 6 CH-8092 Z\"urich, Switzerland ; 'Pregosin, Paul S.' ; Laboratory of Inorganic Chemistry, Universit\"atstr. 6 CH-8092 Z\"urich, Switzerland ; _publ_section_abstract ; A series of organometallic chiral complexes of palladium containing the chelate Duphos, 1, (1+1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene) have been prepared. These include the 1,3-diphenyl allyl cationic compound, [Pd(PhCHCHCHPh)(1)](CF3SO3), 2, the Pd(0) fumaronitrile, complex Pd(NCCH=CHCN)(1), 3, and the penta-fluoro phenyl derivatives Pd(R)(C6F5)(1), 4a-c, R=Me, Et, n-Bu, respectively. The solid state structures of 2 and 4a have been determined by X-ray diffraction. The structure of complex 4a deviates markedly from the expected square planar geometry. Duphos 1 affords a ca 98% ee in the enantioselective allylic alkylation reaction of a 1,3-diphenyl allyl precursor. Detailed 1H and 13CNMR results are reported. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H31 F5 P2 Pd' _chemical_formula_weight 594.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Pd' 'Pd' -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P2(1)2(1)2(1)' loop_ _symmetry_equiv_pos_as_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 10.6352(16) _cell_length_b 14.242(2) _cell_length_c 17.120(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2593.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6112 _cell_measurement_theta_min 3 _cell_measurement_theta_max 52.78 _exptl_crystal_description 'plate' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.886 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.614694 _exptl_absorpt_correction_T_max 0.884148 _exptl_absorpt_process_details ; 'Program Sadabs, G. Sheldrick, 1997, G\"ottingen' ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART PLATFORM, CCD Detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% . _diffrn_reflns_number 19409 _diffrn_reflns_av_R_equivalents 0.0885 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.39 _reflns_number_total 5321 _reflns_number_gt 4036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0262P)^2^+4.2033P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5321 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1103 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.146 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.007 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 0.17966(4) 0.50727(3) 0.88721(3) 0.04173(14) Uani 1 1 d . . . P1 P 0.00112(17) 0.57993(13) 0.85087(10) 0.0447(4) Uani 1 1 d . . . C1L C 0.0877(6) 0.4455(4) 0.9894(3) 0.0301(13) Uani 1 1 d . . . H1LA H 0.1331 0.4627 1.0358 0.045 Uiso 1 1 calc R . . H1LB H 0.0867 0.3784 0.9844 0.045 Uiso 1 1 calc R . . H1LC H 0.0030 0.4684 0.9930 0.045 Uiso 1 1 calc R . . F1 F 0.3440(5) 0.6065(3) 1.0104(3) 0.0879(16) Uani 1 1 d . . . C1L' C 0.3503(6) 0.4655(5) 0.9369(4) 0.0480(18) Uani 1 1 d . . . C1 C -0.1732(8) 0.4727(6) 0.7623(5) 0.087(3) Uani 1 1 d . . . H1A H -0.2520 0.4399 0.7634 0.131 Uiso 1 1 calc R . . H1B H -0.1071 0.4297 0.7490 0.131 Uiso 1 1 calc R . . H1C H -0.1769 0.5218 0.7240 0.131 Uiso 1 1 calc R . . P2 P 0.26405(16) 0.56635(13) 0.77465(10) 0.0431(4) Uani 1 1 d . . . C2L' C 0.4040(7) 0.5241(6) 0.9907(5) 0.062(2) Uani 1 1 d . . . C2 C -0.1474(6) 0.5148(6) 0.8419(4) 0.061(2) Uani 1 1 d . . . H2A H -0.1412 0.4618 0.8782 0.073 Uiso 1 1 calc R . . F2 F 0.5614(5) 0.5699(4) 1.0804(3) 0.1025(18) Uani 1 1 d . . . F3 F 0.6924(5) 0.4126(4) 1.0475(3) 0.1099(19) Uani 1 1 d . . . C3L' C 0.5158(7) 0.5076(9) 1.0289(5) 0.076(2) Uani 1 1 d . . . C3 C -0.2477(7) 0.5806(8) 0.8758(6) 0.091(3) Uani 1 1 d . . . H3A H -0.2728 0.6267 0.8371 0.109 Uiso 1 1 calc R . . H3B H -0.3214 0.5451 0.8913 0.109 Uiso 1 1 calc R . . C4 C -0.1903(10) 0.6279(8) 0.9450(6) 0.098(3) Uani 1 1 d . . . H4A H -0.1779 0.5830 0.9869 0.117 Uiso 1 1 calc R . . H4B H -0.2453 0.6774 0.9637 0.117 Uiso 1 1 calc R . . C4L' C 0.5803(8) 0.4282(8) 1.0125(6) 0.075(3) Uani 1 1 d . . . F4 F 0.5948(6) 0.2875(5) 0.9441(4) 0.125(2) Uani 1 1 d . . . F5 F 0.3745(6) 0.3210(4) 0.8747(3) 0.1013(18) Uani 1 1 d . . . C5 C -0.0628(8) 0.6696(6) 0.9191(5) 0.067(2) Uani 1 1 d . . . H5A H -0.0800 0.7265 0.8889 0.081 Uiso 1 1 calc R . . C5L' C 0.5313(9) 0.3684(7) 0.9595(6) 0.078(3) Uani 1 1 d . . . C6L' C 0.4124(8) 0.3873(5) 0.9217(4) 0.059(2) Uani 1 1 d . . . C6 C 0.0264(10) 0.6964(7) 0.9861(5) 0.096(3) Uani 1 1 d . . . H6A H -0.0129 0.7432 1.0183 0.144 Uiso 1 1 calc R . . H6B H 0.1031 0.7211 0.9648 0.144 Uiso 1 1 calc R . . H6C H 0.0446 0.6418 1.0169 0.144 Uiso 1 1 calc R . . C7 C 0.0275(6) 0.6455(5) 0.7603(4) 0.0433(16) Uani 1 1 d . . . C8 C -0.0642(7) 0.7007(5) 0.7248(4) 0.058(2) Uani 1 1 d . . . H8A H -0.1439 0.7049 0.7468 0.070 Uiso 1 1 calc R . . C9 C -0.0370(8) 0.7494(6) 0.6569(5) 0.066(2) Uani 1 1 d . . . H9A H -0.0982 0.7870 0.6339 0.079 Uiso 1 1 calc R . . C10 C 0.0784(8) 0.7424(5) 0.6239(4) 0.060(2) Uani 1 1 d . . . H10A H 0.0960 0.7755 0.5784 0.072 Uiso 1 1 calc R . . C11 C 0.1701(7) 0.6868(5) 0.6571(4) 0.0520(17) Uani 1 1 d . . . H11A H 0.2480 0.6811 0.6329 0.062 Uiso 1 1 calc R . . C12 C 0.1471(6) 0.6391(4) 0.7264(4) 0.0398(16) Uani 1 1 d . . . C18 C 0.3999(9) 0.7391(6) 0.7898(6) 0.088(3) Uani 1 1 d . . . H18A H 0.4817 0.7673 0.7931 0.132 Uiso 1 1 calc R . . H18B H 0.3532 0.7532 0.8364 0.132 Uiso 1 1 calc R . . H18C H 0.3562 0.7637 0.7452 0.132 Uiso 1 1 calc R . . C17 C 0.4135(7) 0.6337(5) 0.7816(5) 0.062(2) Uani 1 1 d . . . H17A H 0.4560 0.6118 0.8290 0.074 Uiso 1 1 calc R . . C16 C 0.4933(7) 0.5991(6) 0.7122(5) 0.066(2) Uani 1 1 d . . . H16A H 0.4726 0.6342 0.6654 0.079 Uiso 1 1 calc R . . H16B H 0.5821 0.6075 0.7231 0.079 Uiso 1 1 calc R . . C15 C 0.4643(6) 0.4969(7) 0.7009(4) 0.068(2) Uani 1 1 d . . . H15A H 0.4961 0.4605 0.7444 0.082 Uiso 1 1 calc R . . H15B H 0.5029 0.4740 0.6532 0.082 Uiso 1 1 calc R . . C14 C 0.3214(6) 0.4882(5) 0.6959(3) 0.0508(15) Uani 1 1 d . . . H14A H 0.2951 0.5158 0.6460 0.061 Uiso 1 1 calc R . . C13 C 0.2711(8) 0.3878(6) 0.6985(4) 0.072(2) Uani 1 1 d . . . H13A H 0.3051 0.3526 0.6556 0.108 Uiso 1 1 calc R . . H13B H 0.1810 0.3888 0.6948 0.108 Uiso 1 1 calc R . . H13C H 0.2955 0.3588 0.7468 0.108 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 0.0469(2) 0.0400(3) 0.0383(2) 0.0035(2) -0.0021(2) 0.0034(3) P1 0.0457(10) 0.0442(11) 0.0442(9) 0.0038(8) 0.0033(8) 0.0052(8) C1L 0.043(4) 0.029(3) 0.018(3) -0.005(2) -0.004(3) 0.003(3) F1 0.092(4) 0.066(3) 0.105(4) -0.022(3) -0.027(3) 0.007(3) C1L' 0.050(4) 0.050(4) 0.044(4) 0.011(3) -0.004(3) 0.003(3) C1 0.073(5) 0.091(7) 0.099(6) -0.005(5) -0.018(6) -0.014(6) P2 0.0384(9) 0.0483(11) 0.0426(9) 0.0061(8) -0.0025(8) 0.0006(8) C2L' 0.062(5) 0.058(6) 0.067(5) 0.010(4) -0.003(4) -0.001(4) C2 0.054(4) 0.063(5) 0.067(4) 0.022(4) -0.008(3) -0.004(4) F2 0.100(4) 0.109(4) 0.099(4) 0.002(3) -0.041(3) -0.020(4) F3 0.065(3) 0.142(5) 0.123(4) 0.044(4) -0.022(3) 0.017(4) C3L' 0.058(5) 0.099(7) 0.072(5) 0.019(6) -0.024(4) -0.023(6) C3 0.045(5) 0.125(8) 0.103(8) 0.033(7) 0.020(5) 0.013(5) C4 0.089(7) 0.129(9) 0.076(6) 0.007(6) 0.031(6) 0.044(7) C4L' 0.055(5) 0.091(7) 0.079(6) 0.036(6) -0.005(5) 0.008(5) F4 0.121(5) 0.114(5) 0.140(5) 0.002(4) 0.000(4) 0.075(4) F5 0.124(4) 0.086(4) 0.094(4) -0.015(3) -0.022(3) 0.042(3) C5 0.080(6) 0.062(5) 0.060(5) -0.008(4) 0.012(5) 0.025(5) C5L' 0.074(6) 0.078(7) 0.083(6) 0.023(5) 0.000(6) 0.021(5) C6L' 0.083(6) 0.039(4) 0.055(4) -0.005(4) 0.019(4) 0.008(4) C6 0.138(10) 0.078(7) 0.073(6) -0.037(5) 0.002(7) 0.023(7) C7 0.050(4) 0.037(4) 0.043(4) 0.000(3) -0.003(3) 0.005(3) C8 0.043(4) 0.062(5) 0.070(5) 0.008(4) -0.003(4) 0.011(4) C9 0.071(6) 0.064(6) 0.063(5) 0.019(4) -0.015(5) 0.010(4) C10 0.077(5) 0.052(4) 0.051(4) 0.025(4) 0.006(4) 0.008(4) C11 0.053(4) 0.058(4) 0.044(4) 0.011(3) -0.004(4) -0.003(4) C12 0.039(4) 0.041(4) 0.040(3) 0.004(3) -0.009(3) -0.002(3) C18 0.090(7) 0.064(6) 0.111(8) -0.005(5) -0.021(6) -0.028(5) C17 0.055(5) 0.061(5) 0.069(5) 0.017(4) -0.022(4) -0.011(4) C16 0.041(4) 0.079(6) 0.078(6) 0.022(5) 0.003(4) -0.001(4) C15 0.053(4) 0.082(6) 0.070(5) 0.007(6) 0.005(4) 0.011(5) C14 0.050(3) 0.063(4) 0.040(3) -0.001(3) 0.002(3) 0.011(5) C13 0.087(6) 0.065(6) 0.064(5) -0.012(4) -0.004(5) 0.006(5) _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 C1L' 2.091(7) . ? Pd1 C1L 2.189(5) . ? Pd1 P1 2.2502(19) . ? Pd1 P2 2.2863(18) . ? P1 C7 1.832(7) . ? P1 C2 1.838(7) . ? P1 C5 1.859(7) . ? F1 C2L' 1.378(9) . ? C1L' C6L' 1.320(9) . ? C1L' C2L' 1.368(10) . ? C1 C2 1.514(11) . ? P2 C12 1.818(6) . ? P2 C14 1.851(6) . ? P2 C17 1.861(8) . ? C2L' C3L' 1.377(10) . ? C2 C3 1.533(11) . ? F2 C3L' 1.342(11) . ? F3 C4L' 1.353(10) . ? C3L' C4L' 1.351(13) . ? C3 C4 1.494(13) . ? C4 C5 1.545(13) . ? C4L' C5L' 1.350(13) . ? F4 C5L' 1.360(10) . ? F5 C6L' 1.304(9) . ? C5 C6 1.536(12) . ? C5L' C6L' 1.446(12) . ? C7 C8 1.392(9) . ? C7 C12 1.401(9) . ? C8 C9 1.383(10) . ? C9 C10 1.356(11) . ? C10 C11 1.379(10) . ? C11 C12 1.389(9) . ? C18 C17 1.515(10) . ? C17 C16 1.542(11) . ? C16 C15 1.500(12) . ? C15 C14 1.527(9) . ? C14 C13 1.528(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1L' Pd1 C1L 87.0(2) . . ? C1L' Pd1 P1 167.4(2) . . ? C1L Pd1 P1 91.65(16) . . ? C1L' Pd1 P2 96.13(18) . . ? C1L Pd1 P2 175.57(16) . . ? P1 Pd1 P2 85.93(6) . . ? C7 P1 C2 108.5(3) . . ? C7 P1 C5 103.8(3) . . ? C2 P1 C5 94.9(4) . . ? C7 P1 Pd1 109.8(2) . . ? C2 P1 Pd1 121.1(3) . . ? C5 P1 Pd1 116.8(3) . . ? C6L' C1L' C2L' 116.0(7) . . ? C6L' C1L' Pd1 126.5(6) . . ? C2L' C1L' Pd1 117.5(5) . . ? C12 P2 C14 103.7(3) . . ? C12 P2 C17 108.7(3) . . ? C14 P2 C17 94.3(4) . . ? C12 P2 Pd1 108.9(2) . . ? C14 P2 Pd1 121.5(2) . . ? C17 P2 Pd1 118.1(3) . . ? C1L' C2L' F1 119.4(7) . . ? C1L' C2L' C3L' 125.1(9) . . ? F1 C2L' C3L' 115.4(8) . . ? C1 C2 C3 117.1(7) . . ? C1 C2 P1 115.5(5) . . ? C3 C2 P1 105.0(6) . . ? C4L' C3L' F2 120.4(8) . . ? C4L' C3L' C2L' 118.8(9) . . ? F2 C3L' C2L' 120.7(10) . . ? C4 C3 C2 107.0(7) . . ? C3 C4 C5 107.7(7) . . ? C3L' C4L' F3 119.5(10) . . ? C3L' C4L' C5L' 118.2(8) . . ? F3 C4L' C5L' 122.3(10) . . ? C6 C5 C4 115.1(8) . . ? C6 C5 P1 114.5(6) . . ? C4 C5 P1 103.7(6) . . ? C4L' C5L' F4 118.3(9) . . ? C4L' C5L' C6L' 121.3(8) . . ? F4 C5L' C6L' 120.3(9) . . ? F5 C6L' C1L' 125.3(8) . . ? F5 C6L' C5L' 114.3(7) . . ? C1L' C6L' C5L' 120.4(8) . . ? C8 C7 C12 119.5(6) . . ? C8 C7 P1 123.4(5) . . ? C12 C7 P1 117.2(5) . . ? C9 C8 C7 120.2(7) . . ? C10 C9 C8 120.2(7) . . ? C9 C10 C11 120.7(7) . . ? C12 C11 C10 120.5(7) . . ? C11 C12 C7 118.8(6) . . ? C11 C12 P2 123.1(5) . . ? C7 C12 P2 118.1(5) . . ? C18 C17 C16 116.2(7) . . ? C18 C17 P2 115.8(6) . . ? C16 C17 P2 104.8(5) . . ? C15 C16 C17 107.2(6) . . ? C16 C15 C14 106.9(7) . . ? C13 C14 C15 115.0(7) . . ? C13 C14 P2 115.2(5) . . ? C15 C14 P2 103.8(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.513 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.114 # ---end-of-data-block---