Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_welt46 _database_code_depnum_ccdc_archive 'CCDC 627975' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 Cl N O3 P Pd' _chemical_formula_sum 'C19 H21 Cl N O3 P Pd' _chemical_formula_weight 484.19 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' N N 0.0061 0.0033 '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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.79900(10) _cell_length_b 16.2160(2) _cell_length_c 21.6790(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3796.35(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14941 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 1.222 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.828 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_reflns_av_R_equivalents 0.049 _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5540 _diffrn_reflns_av_sigmaI/netI 0.1135 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5539 _reflns_number_gt 3422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0000P)^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 5539 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 0.767 _refine_ls_restrained_S_all 0.767 _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 Pd Pd 0.84787(2) 0.083440(14) 0.521098(11) 0.01912(8) Uani 1 1 d . . . Cl Cl 0.89997(8) 0.13802(5) 0.42199(4) 0.02589(18) Uani 1 1 d . . . P P 0.78109(8) 0.02481(5) 0.60431(4) 0.02049(18) Uani 1 1 d . . . O1 O 1.1073(2) 0.18043(14) 0.65455(10) 0.0272(5) Uani 1 1 d . . . O2 O 0.8602(2) 0.04817(14) 0.66523(10) 0.0243(5) Uani 1 1 d . . . O3 O 0.7864(2) -0.07489(12) 0.60323(10) 0.0215(5) Uani 1 1 d . . . N N 0.9833(2) 0.15563(15) 0.57322(12) 0.0196(6) Uani 1 1 d . . . C1 C 1.1492(3) 0.2166(2) 0.51107(16) 0.0255(7) Uani 1 1 d . . . H1A H 1.2060 0.1754 0.5282 0.038 Uiso 1 1 calc . . . H1B H 1.1950 0.2672 0.5017 0.038 Uiso 1 1 calc . . . H1C H 1.1116 0.1951 0.4732 0.038 Uiso 1 1 calc . . . C2 C 0.9584(3) 0.2994(2) 0.53513(16) 0.0264(7) Uani 1 1 d . . . H2A H 0.8940 0.3081 0.5663 0.040 Uiso 1 1 calc . . . H2B H 0.9202 0.2806 0.4966 0.040 Uiso 1 1 calc . . . H2C H 1.0025 0.3513 0.5278 0.040 Uiso 1 1 calc . . . C3 C 1.0483(3) 0.23528(18) 0.55775(15) 0.0200(7) Uani 1 1 d . . . C4 C 1.1040(3) 0.2583(2) 0.62080(16) 0.0278(7) Uani 1 1 d . . . H4A H 1.1883 0.2814 0.6160 0.033 Uiso 1 1 calc . . . H4B H 1.0513 0.2992 0.6423 0.033 Uiso 1 1 calc . . . C5 C 1.0259(3) 0.1318(2) 0.62505(15) 0.0227(7) Uani 1 1 d . . . C6 C 0.9928(3) 0.0532(2) 0.65768(16) 0.0280(8) Uani 1 1 d . . . H6A H 1.0225 0.0054 0.6334 0.034 Uiso 1 1 calc . . . H6B H 1.0335 0.0517 0.6986 0.034 Uiso 1 1 calc . . . C7 C 0.7183(3) 0.0130(2) 0.47669(15) 0.0307(8) Uani 1 1 d . . . H7A H 0.6675 -0.0160 0.5072 0.046 Uiso 1 1 calc . . . H7B H 0.7601 -0.0273 0.4502 0.046 Uiso 1 1 calc . . . H7C H 0.6654 0.0486 0.4514 0.046 Uiso 1 1 calc . . . C8 C 0.7472(3) -0.1187(2) 0.65502(14) 0.0223(7) Uani 1 1 d . . . C9 C 0.8118(3) -0.1900(2) 0.66863(15) 0.0280(8) Uani 1 1 d . . . H9 H 0.8811 -0.2059 0.6444 0.034 Uiso 1 1 calc . . . C10 C 0.7742(4) -0.2377(2) 0.71805(17) 0.0394(10) Uani 1 1 d . . . H10 H 0.8166 -0.2875 0.7274 0.047 Uiso 1 1 calc . . . C11 C 0.6751(4) -0.2131(2) 0.75371(18) 0.0393(10) Uani 1 1 d . . . H11 H 0.6506 -0.2454 0.7881 0.047 Uiso 1 1 calc . . . C12 C 0.6114(3) -0.1420(2) 0.73980(16) 0.0317(8) Uani 1 1 d . . . H12 H 0.5439 -0.1258 0.7651 0.038 Uiso 1 1 calc . . . C13 C 0.6441(3) -0.09287(19) 0.68895(14) 0.0215(7) Uani 1 1 d . . . C14 C 0.5729(3) -0.0190(2) 0.67126(14) 0.0226(7) Uani 1 1 d . . . C15 C 0.4505(3) -0.0065(2) 0.68997(15) 0.0298(8) Uani 1 1 d . . . H15 H 0.4107 -0.0467 0.7150 0.036 Uiso 1 1 calc . . . C16 C 0.3861(3) 0.0640(3) 0.67235(17) 0.0359(9) Uani 1 1 d . . . H16 H 0.3035 0.0718 0.6861 0.043 Uiso 1 1 calc . . . C17 C 0.4408(4) 0.1226(2) 0.63510(17) 0.0347(9) Uani 1 1 d . . . H17 H 0.3963 0.1707 0.6235 0.042 Uiso 1 1 calc . . . C18 C 0.5608(3) 0.1107(2) 0.61484(15) 0.0286(8) Uani 1 1 d . . . H18 H 0.5982 0.1503 0.5885 0.034 Uiso 1 1 calc . . . C19 C 0.6275(3) 0.04076(19) 0.63290(14) 0.0216(7) Uani 1 1 d . . . 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 Pd 0.02209(13) 0.01846(13) 0.01681(13) 0.00075(10) -0.00011(10) -0.00222(10) Cl 0.0277(4) 0.0297(4) 0.0203(4) 0.0031(3) 0.0021(3) 0.0013(4) P 0.0241(4) 0.0191(4) 0.0182(4) 0.0004(3) 0.0004(3) -0.0030(4) O1 0.0278(12) 0.0282(13) 0.0256(12) 0.0002(10) -0.0070(11) -0.0063(11) O2 0.0249(12) 0.0279(12) 0.0201(12) 0.0006(10) -0.0008(10) -0.0076(10) O3 0.0264(12) 0.0168(11) 0.0212(11) 0.0027(9) 0.0049(10) 0.0003(10) N 0.0195(14) 0.0208(14) 0.0184(13) 0.0011(11) 0.0005(11) -0.0025(11) C1 0.0211(16) 0.0266(17) 0.0289(19) 0.0026(14) 0.0033(14) -0.0021(15) C2 0.0211(16) 0.0237(17) 0.034(2) 0.0006(15) 0.0019(15) 0.0005(15) C3 0.0186(15) 0.0173(15) 0.0241(16) -0.0004(13) 0.0017(13) -0.0023(13) C4 0.0282(17) 0.0239(17) 0.0313(18) -0.0025(15) -0.0009(16) -0.0068(15) C5 0.0202(16) 0.0242(17) 0.0238(17) -0.0007(14) 0.0026(14) -0.0024(14) C6 0.0286(19) 0.0306(18) 0.0249(17) 0.0050(15) -0.0061(15) -0.0043(16) C7 0.036(2) 0.0296(19) 0.0264(18) -0.0024(15) -0.0063(16) -0.0087(16) C8 0.0287(17) 0.0210(16) 0.0172(15) -0.0005(13) -0.0010(14) -0.0071(14) C9 0.035(2) 0.0238(18) 0.0252(18) 0.0020(15) -0.0028(15) 0.0023(16) C10 0.057(3) 0.029(2) 0.032(2) 0.0083(17) -0.0044(19) 0.0064(19) C11 0.055(3) 0.035(2) 0.0286(19) 0.0149(18) 0.0021(19) -0.004(2) C12 0.037(2) 0.035(2) 0.0225(18) 0.0041(15) 0.0056(16) -0.0071(17) C13 0.0260(17) 0.0218(16) 0.0168(15) -0.0003(12) 0.0007(13) -0.0072(14) C14 0.0263(17) 0.0231(16) 0.0184(16) -0.0044(13) 0.0016(13) -0.0012(15) C15 0.0288(19) 0.039(2) 0.0218(17) -0.0048(15) 0.0034(15) -0.0045(17) C16 0.0267(19) 0.052(2) 0.029(2) -0.0117(18) 0.0000(16) 0.0098(18) C17 0.040(2) 0.037(2) 0.0273(19) -0.0050(17) -0.0040(17) 0.0144(18) C18 0.039(2) 0.0244(17) 0.0229(18) -0.0012(14) -0.0011(16) 0.0018(16) C19 0.0245(17) 0.0212(16) 0.0191(16) -0.0043(13) -0.0012(13) -0.0005(14) _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 Pd C7 2.047(3) . ? Pd P 2.1629(8) . ? Pd N 2.187(3) . ? Pd Cl 2.3909(8) . ? P O2 1.618(2) . ? P O3 1.618(2) . ? P C19 1.790(3) . ? O1 C5 1.343(4) . ? O1 C4 1.460(4) . ? O2 C6 1.444(4) . ? O3 C8 1.395(4) . ? N C5 1.274(4) . ? N C3 1.508(4) . ? C1 C3 1.517(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.505(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.539(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.501(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.382(5) . ? C8 C13 1.398(4) . ? C9 C10 1.383(5) . ? C9 H9 0.9500 . ? C10 C11 1.380(5) . ? C10 H10 0.9500 . ? C11 C12 1.375(5) . ? C11 H11 0.9500 . ? C12 C13 1.406(4) . ? C12 H12 0.9500 . ? C13 C14 1.474(4) . ? C14 C15 1.398(4) . ? C14 C19 1.406(4) . ? C15 C16 1.391(5) . ? C15 H15 0.9500 . ? C16 C17 1.380(5) . ? C16 H16 0.9500 . ? C17 C18 1.381(5) . ? C17 H17 0.9500 . ? C18 C19 1.400(5) . ? C18 H18 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 C7 Pd P 85.36(10) . . ? C7 Pd N 176.92(12) . . ? P Pd N 91.56(7) . . ? C7 Pd Cl 86.83(10) . . ? P Pd Cl 172.18(3) . . ? N Pd Cl 96.25(7) . . ? O2 P O3 103.12(12) . . ? O2 P C19 99.95(13) . . ? O3 P C19 100.52(13) . . ? O2 P Pd 113.69(9) . . ? O3 P Pd 114.54(9) . . ? C19 P Pd 122.30(11) . . ? C5 O1 C4 104.6(2) . . ? C6 O2 P 116.4(2) . . ? C8 O3 P 119.1(2) . . ? C5 N C3 106.7(3) . . ? C5 N Pd 122.3(2) . . ? C3 N Pd 130.90(19) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C2 C3 N 111.3(2) . . ? C2 C3 C1 112.6(3) . . ? N C3 C1 108.2(2) . . ? C2 C3 C4 111.9(3) . . ? N C3 C4 101.1(2) . . ? C1 C3 C4 111.1(3) . . ? O1 C4 C3 104.2(2) . . ? O1 C4 H4A 110.9 . . ? C3 C4 H4A 110.9 . . ? O1 C4 H4B 110.9 . . ? C3 C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? N C5 O1 118.6(3) . . ? N C5 C6 126.0(3) . . ? O1 C5 C6 115.4(3) . . ? O2 C6 C5 109.7(3) . . ? O2 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? O2 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? Pd C7 H7A 109.5 . . ? Pd C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Pd C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 O3 116.4(3) . . ? C9 C8 C13 122.7(3) . . ? O3 C8 C13 120.9(3) . . ? C8 C9 C10 119.0(3) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 121.4(3) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C8 C13 C12 116.3(3) . . ? C8 C13 C14 121.4(3) . . ? C12 C13 C14 122.3(3) . . ? C15 C14 C19 117.9(3) . . ? C15 C14 C13 122.4(3) . . ? C19 C14 C13 119.7(3) . . ? C16 C15 C14 120.8(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.8(3) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 119.5(3) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 120.4(3) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 120.6(3) . . ? C18 C19 P 119.8(3) . . ? C14 C19 P 119.6(2) . . ? 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 C7 Pd P O2 174.25(15) . . . . ? N Pd P O2 -5.67(12) . . . . ? Cl Pd P O2 177.7(2) . . . . ? C7 Pd P O3 56.04(14) . . . . ? N Pd P O3 -123.89(12) . . . . ? Cl Pd P O3 59.4(3) . . . . ? C7 Pd P C19 -65.70(16) . . . . ? N Pd P C19 114.38(14) . . . . ? Cl Pd P C19 -62.3(3) . . . . ? O3 P O2 C6 84.6(2) . . . . ? C19 P O2 C6 -172.0(2) . . . . ? Pd P O2 C6 -40.0(3) . . . . ? O2 P O3 C8 55.0(2) . . . . ? C19 P O3 C8 -47.9(3) . . . . ? Pd P O3 C8 179.1(2) . . . . ? C7 Pd N C5 24(2) . . . . ? P Pd N C5 25.4(3) . . . . ? Cl Pd N C5 -155.0(2) . . . . ? C7 Pd N C3 -159(2) . . . . ? P Pd N C3 -157.8(2) . . . . ? Cl Pd N C3 21.7(2) . . . . ? C5 N C3 C2 -134.5(3) . . . . ? Pd N C3 C2 48.3(3) . . . . ? C5 N C3 C1 101.3(3) . . . . ? Pd N C3 C1 -75.8(3) . . . . ? C5 N C3 C4 -15.5(3) . . . . ? Pd N C3 C4 167.4(2) . . . . ? C5 O1 C4 C3 -19.8(3) . . . . ? C2 C3 C4 O1 139.7(3) . . . . ? N C3 C4 O1 21.1(3) . . . . ? C1 C3 C4 O1 -93.5(3) . . . . ? C3 N C5 O1 3.6(4) . . . . ? Pd N C5 O1 -179.0(2) . . . . ? C3 N C5 C6 -176.9(3) . . . . ? Pd N C5 C6 0.5(5) . . . . ? C4 O1 C5 N 11.0(4) . . . . ? C4 O1 C5 C6 -168.6(3) . . . . ? P O2 C6 C5 75.6(3) . . . . ? N C5 C6 O2 -54.8(4) . . . . ? O1 C5 C6 O2 124.7(3) . . . . ? P O3 C8 C9 -144.1(3) . . . . ? P O3 C8 C13 38.7(4) . . . . ? O3 C8 C9 C10 -177.5(3) . . . . ? C13 C8 C9 C10 -0.5(5) . . . . ? C8 C9 C10 C11 -1.4(6) . . . . ? C9 C10 C11 C12 1.3(6) . . . . ? C10 C11 C12 C13 0.6(6) . . . . ? C9 C8 C13 C12 2.2(5) . . . . ? O3 C8 C13 C12 179.2(3) . . . . ? C9 C8 C13 C14 -176.6(3) . . . . ? O3 C8 C13 C14 0.3(5) . . . . ? C11 C12 C13 C8 -2.3(5) . . . . ? C11 C12 C13 C14 176.6(3) . . . . ? C8 C13 C14 C15 158.3(3) . . . . ? C12 C13 C14 C15 -20.5(5) . . . . ? C8 C13 C14 C19 -20.0(5) . . . . ? C12 C13 C14 C19 161.2(3) . . . . ? C19 C14 C15 C16 -1.7(5) . . . . ? C13 C14 C15 C16 -180.0(3) . . . . ? C14 C15 C16 C17 1.2(5) . . . . ? C15 C16 C17 C18 0.4(6) . . . . ? C16 C17 C18 C19 -1.3(5) . . . . ? C17 C18 C19 C14 0.8(5) . . . . ? C17 C18 C19 P 178.1(3) . . . . ? C15 C14 C19 C18 0.7(5) . . . . ? C13 C14 C19 C18 179.0(3) . . . . ? C15 C14 C19 P -176.6(2) . . . . ? C13 C14 C19 P 1.8(4) . . . . ? O2 P C19 C18 105.2(3) . . . . ? O3 P C19 C18 -149.3(3) . . . . ? Pd P C19 C18 -21.2(3) . . . . ? O2 P C19 C14 -77.5(3) . . . . ? O3 P C19 C14 28.0(3) . . . . ? Pd P C19 C14 156.1(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.897 _refine_diff_density_min -0.729 _refine_diff_density_rms 0.120 data_compound_10b _database_code_depnum_ccdc_archive 'CCDC 627976' _audit_creation_date 22-1-05 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 Cl N O3 P Pd' _chemical_formula_sum 'C21 H25 Cl N O3 P Pd' _chemical_formula_weight 512.24 _chemical_absolute_configuration . 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' 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 'P 21/N' _symmetry_space_group_name_Hall '-P 2yn' 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 12.4150(3) _cell_length_b 10.8760(2) _cell_length_c 15.5810(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.3340(9) _cell_angle_gamma 90.00 _cell_volume 2090.99(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11007 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 1.114 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6117 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0927 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 30.05 _reflns_number_total 6116 _reflns_number_gt 4353 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0476P)^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 6116 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _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 Pd Pd 1.03295(2) 0.01244(2) 0.779266(16) 0.02222(9) Uani 1 1 d . . . Cl Cl 1.17629(7) -0.03969(9) 0.88902(6) 0.0307(2) Uani 1 1 d . . . P P 0.90194(7) 0.08704(8) 0.69280(6) 0.02109(18) Uani 1 1 d . . . O1 O 1.0460(2) -0.2322(2) 0.55960(15) 0.0273(5) Uani 1 1 d . . . O2 O 0.88326(19) 0.0180(2) 0.60092(15) 0.0207(5) Uani 1 1 d . . . O3 O 0.78392(19) 0.0828(2) 0.72743(15) 0.0255(5) Uani 1 1 d . . . N N 1.0742(2) -0.1150(2) 0.67919(18) 0.0220(6) Uani 1 1 d . . . C1 C 1.2762(3) -0.0972(3) 0.6855(2) 0.0299(8) Uani 1 1 d . . . H1A H 1.2626 -0.0270 0.6463 0.045 Uiso 1 1 calc . . . H1B H 1.3412 -0.1409 0.6720 0.045 Uiso 1 1 calc . . . H1C H 1.2870 -0.0676 0.7452 0.045 Uiso 1 1 calc . . . C2 C 1.1872(3) -0.2851(3) 0.7423(2) 0.0306(8) Uani 1 1 d . . . H2A H 1.1904 -0.2484 0.8000 0.046 Uiso 1 1 calc . . . H2B H 1.2528 -0.3339 0.7380 0.046 Uiso 1 1 calc . . . H2C H 1.1233 -0.3384 0.7325 0.046 Uiso 1 1 calc . . . C3 C 1.1796(3) -0.1838(3) 0.6746(2) 0.0239(7) Uani 1 1 d . . . C4 C 1.1636(3) -0.2374(3) 0.5832(2) 0.0283(8) Uani 1 1 d . . . H4A H 1.2022 -0.1877 0.5431 0.034 Uiso 1 1 calc . . . H4B H 1.1902 -0.3232 0.5827 0.034 Uiso 1 1 calc . . . C5 C 1.0090(3) -0.1514(3) 0.6152(2) 0.0224(7) Uani 1 1 d . . . C6 C 0.8899(3) -0.1157(3) 0.5930(2) 0.0235(7) Uani 1 1 d . . . C7 C 0.9824(3) 0.1380(4) 0.8657(2) 0.0318(8) Uani 1 1 d . . . H7A H 0.9248 0.1895 0.8365 0.048 Uiso 1 1 calc . . . H7B H 1.0436 0.1899 0.8881 0.048 Uiso 1 1 calc . . . H7C H 0.9547 0.0941 0.9137 0.048 Uiso 1 1 calc . . . C8 C 0.6945(3) 0.1287(3) 0.6728(2) 0.0256(7) Uani 1 1 d . . . C9 C 0.5996(3) 0.0628(4) 0.6715(3) 0.0334(8) Uani 1 1 d . . . H9 H 0.5962 -0.0096 0.7052 0.040 Uiso 1 1 calc . . . C10 C 0.5090(3) 0.1049(5) 0.6197(3) 0.0426(10) Uani 1 1 d . . . H10 H 0.4431 0.0600 0.6168 0.051 Uiso 1 1 calc . . . C11 C 0.5139(3) 0.2114(4) 0.5726(3) 0.0418(10) Uani 1 1 d . . . H11 H 0.4511 0.2406 0.5384 0.050 Uiso 1 1 calc . . . C12 C 0.6099(3) 0.2758(4) 0.5749(2) 0.0332(8) Uani 1 1 d . . . H12 H 0.6126 0.3485 0.5413 0.040 Uiso 1 1 calc . . . C13 C 0.7038(3) 0.2362(3) 0.6258(2) 0.0250(7) Uani 1 1 d . . . C14 C 0.8080(3) 0.3027(3) 0.6271(2) 0.0234(7) Uani 1 1 d . . . C15 C 0.8140(3) 0.4233(3) 0.5973(2) 0.0293(8) Uani 1 1 d . . . H15 H 0.7492 0.4671 0.5791 0.035 Uiso 1 1 calc . . . C16 C 0.9133(4) 0.4799(3) 0.5940(3) 0.0320(8) Uani 1 1 d . . . H16 H 0.9158 0.5610 0.5717 0.038 Uiso 1 1 calc . . . C17 C 1.0095(3) 0.4200(3) 0.6227(2) 0.0313(8) Uani 1 1 d . . . H17 H 1.0772 0.4596 0.6201 0.038 Uiso 1 1 calc . . . C18 C 1.0053(3) 0.3015(3) 0.6554(2) 0.0264(7) Uani 1 1 d . . . H18 H 1.0703 0.2606 0.6770 0.032 Uiso 1 1 calc . . . C19 C 0.9055(3) 0.2425(3) 0.6564(2) 0.0221(7) Uani 1 1 d . . . C20 C 0.8217(3) -0.1813(3) 0.6548(2) 0.0298(8) Uani 1 1 d . . . H20A H 0.8499 -0.1619 0.7146 0.045 Uiso 1 1 calc . . . H20B H 0.8252 -0.2703 0.6457 0.045 Uiso 1 1 calc . . . H20C H 0.7463 -0.1538 0.6439 0.045 Uiso 1 1 calc . . . C21 C 0.8485(3) -0.1418(3) 0.4994(2) 0.0294(8) Uani 1 1 d . . . H21A H 0.7738 -0.1121 0.4875 0.044 Uiso 1 1 calc . . . H21B H 0.8505 -0.2306 0.4889 0.044 Uiso 1 1 calc . . . H21C H 0.8945 -0.0996 0.4615 0.044 Uiso 1 1 calc . . . 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 Pd 0.02688(15) 0.01942(14) 0.01947(14) -0.00093(10) -0.00143(10) 0.00247(10) Cl 0.0339(5) 0.0290(5) 0.0269(4) -0.0001(3) -0.0064(3) 0.0012(4) P 0.0251(4) 0.0187(4) 0.0193(4) -0.0010(3) 0.0013(3) 0.0030(3) O1 0.0311(13) 0.0236(12) 0.0268(13) -0.0085(10) 0.0010(10) 0.0037(10) O2 0.0254(12) 0.0166(11) 0.0196(11) 0.0005(9) 0.0007(9) 0.0017(9) O3 0.0290(13) 0.0266(13) 0.0216(12) 0.0033(10) 0.0062(10) 0.0046(10) N 0.0267(14) 0.0159(13) 0.0231(14) -0.0012(11) 0.0011(11) 0.0026(11) C1 0.0267(18) 0.0257(18) 0.037(2) 0.0032(15) -0.0001(15) 0.0016(14) C2 0.038(2) 0.0200(17) 0.0329(19) 0.0029(15) -0.0013(16) 0.0043(15) C3 0.0272(17) 0.0172(16) 0.0272(17) 0.0002(13) 0.0023(13) 0.0047(13) C4 0.0281(18) 0.0277(18) 0.0291(19) -0.0047(15) 0.0033(14) 0.0045(14) C5 0.0293(17) 0.0157(15) 0.0223(16) 0.0015(13) 0.0027(13) 0.0000(13) C6 0.0262(17) 0.0148(15) 0.0295(18) -0.0006(13) 0.0025(14) 0.0011(13) C7 0.038(2) 0.039(2) 0.0175(16) -0.0115(15) -0.0022(14) 0.0134(17) C8 0.0274(17) 0.0303(19) 0.0203(16) 0.0005(14) 0.0074(13) 0.0052(14) C9 0.032(2) 0.036(2) 0.033(2) 0.0043(17) 0.0098(16) 0.0003(17) C10 0.0230(19) 0.059(3) 0.047(2) 0.005(2) 0.0093(17) -0.0031(18) C11 0.0244(19) 0.057(3) 0.044(2) 0.007(2) 0.0009(17) 0.0047(18) C12 0.0314(19) 0.036(2) 0.032(2) 0.0039(16) 0.0028(16) 0.0081(16) C13 0.0274(17) 0.0264(18) 0.0215(16) -0.0007(14) 0.0039(13) 0.0059(14) C14 0.0292(18) 0.0208(16) 0.0203(16) -0.0043(13) 0.0031(13) 0.0029(13) C15 0.040(2) 0.0206(17) 0.0264(18) -0.0019(14) 0.0006(15) 0.0067(15) C16 0.050(2) 0.0171(16) 0.0289(19) -0.0016(14) 0.0027(17) -0.0008(16) C17 0.040(2) 0.0235(18) 0.0300(19) -0.0036(15) -0.0005(16) -0.0079(16) C18 0.0311(18) 0.0240(17) 0.0233(17) -0.0031(14) -0.0013(14) 0.0008(14) C19 0.0303(18) 0.0170(15) 0.0189(15) -0.0028(12) 0.0022(13) 0.0018(13) C20 0.035(2) 0.0216(18) 0.034(2) 0.0021(15) 0.0097(16) -0.0036(15) C21 0.034(2) 0.0272(19) 0.0249(17) -0.0039(14) -0.0040(15) 0.0017(15) _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 Pd C7 2.064(3) . ? Pd P 2.1530(9) . ? Pd N 2.188(3) . ? Pd Cl 2.3960(9) . ? P O2 1.610(2) . ? P O3 1.617(2) . ? P C19 1.786(3) . ? O1 C5 1.349(4) . ? O1 C4 1.467(4) . ? O2 C6 1.463(4) . ? O3 C8 1.413(4) . ? N C5 1.276(4) . ? N C3 1.517(4) . ? C1 C3 1.519(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.521(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.531(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.531(5) . ? C6 C21 1.518(5) . ? C6 C20 1.528(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.378(5) . ? C8 C13 1.391(5) . ? C9 C10 1.387(6) . ? C9 H9 0.9500 . ? C10 C11 1.376(6) . ? C10 H10 0.9500 . ? C11 C12 1.380(6) . ? C11 H11 0.9500 . ? C12 C13 1.403(5) . ? C12 H12 0.9500 . ? C13 C14 1.480(5) . ? C14 C15 1.397(5) . ? C14 C19 1.408(5) . ? C15 C16 1.384(6) . ? C15 H15 0.9500 . ? C16 C17 1.390(6) . ? C16 H16 0.9500 . ? C17 C18 1.389(5) . ? C17 H17 0.9500 . ? C18 C19 1.396(5) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 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 C7 Pd P 84.03(10) . . ? C7 Pd N 174.75(12) . . ? P Pd N 90.72(7) . . ? C7 Pd Cl 86.91(10) . . ? P Pd Cl 170.43(3) . . ? N Pd Cl 98.34(8) . . ? O2 P O3 103.68(13) . . ? O2 P C19 99.50(13) . . ? O3 P C19 100.85(14) . . ? O2 P Pd 113.92(9) . . ? O3 P Pd 115.49(9) . . ? C19 P Pd 120.79(11) . . ? C5 O1 C4 105.3(2) . . ? C6 O2 P 122.3(2) . . ? C8 O3 P 118.0(2) . . ? C5 N C3 106.6(3) . . ? C5 N Pd 125.1(2) . . ? C3 N Pd 128.1(2) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N C3 C1 111.3(3) . . ? N C3 C2 108.2(3) . . ? C1 C3 C2 112.6(3) . . ? N C3 C4 102.0(3) . . ? C1 C3 C4 111.1(3) . . ? C2 C3 C4 111.1(3) . . ? O1 C4 C3 104.0(3) . . ? O1 C4 H4A 110.9 . . ? C3 C4 H4A 110.9 . . ? O1 C4 H4B 110.9 . . ? C3 C4 H4B 110.9 . . ? H4A C4 H4B 109.0 . . ? N C5 O1 118.2(3) . . ? N C5 C6 127.6(3) . . ? O1 C5 C6 114.1(3) . . ? O2 C6 C21 104.5(3) . . ? O2 C6 C20 111.8(3) . . ? C21 C6 C20 111.4(3) . . ? O2 C6 C5 107.2(3) . . ? C21 C6 C5 112.7(3) . . ? C20 C6 C5 109.1(3) . . ? Pd C7 H7A 109.5 . . ? Pd C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Pd C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 123.3(3) . . ? C9 C8 O3 116.0(3) . . ? C13 C8 O3 120.6(3) . . ? C8 C9 C10 118.3(4) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C11 C10 C9 120.5(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 120.2(4) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 121.3(4) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C8 C13 C12 116.4(3) . . ? C8 C13 C14 121.7(3) . . ? C12 C13 C14 121.8(3) . . ? C15 C14 C19 117.9(3) . . ? C15 C14 C13 122.2(3) . . ? C19 C14 C13 119.8(3) . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 121.1(3) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C18 C17 C16 119.2(4) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 120.0(3) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C14 121.0(3) . . ? C18 C19 P 119.5(3) . . ? C14 C19 P 119.5(3) . . ? C6 C20 H20A 109.5 . . ? C6 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C6 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C6 C21 H21A 109.5 . . ? C6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C7 Pd P O2 -175.53(16) . . . . ? N Pd P O2 4.24(13) . . . . ? Cl Pd P O2 165.7(2) . . . . ? C7 Pd P O3 -55.66(16) . . . . ? N Pd P O3 124.11(13) . . . . ? Cl Pd P O3 -74.4(2) . . . . ? C7 Pd P C19 66.13(18) . . . . ? N Pd P C19 -114.10(15) . . . . ? Cl Pd P C19 47.4(3) . . . . ? O3 P O2 C6 -85.5(2) . . . . ? C19 P O2 C6 170.8(2) . . . . ? Pd P O2 C6 40.8(3) . . . . ? O2 P O3 C8 -53.6(3) . . . . ? C19 P O3 C8 49.0(3) . . . . ? Pd P O3 C8 -179.0(2) . . . . ? C7 Pd N C5 -21.1(16) . . . . ? P Pd N C5 -23.6(3) . . . . ? Cl Pd N C5 159.5(3) . . . . ? C7 Pd N C3 163.8(15) . . . . ? P Pd N C3 161.3(3) . . . . ? Cl Pd N C3 -15.7(3) . . . . ? C5 N C3 C1 132.2(3) . . . . ? Pd N C3 C1 -51.9(4) . . . . ? C5 N C3 C2 -103.5(3) . . . . ? Pd N C3 C2 72.4(3) . . . . ? C5 N C3 C4 13.7(3) . . . . ? Pd N C3 C4 -170.4(2) . . . . ? C5 O1 C4 C3 18.0(3) . . . . ? N C3 C4 O1 -18.9(3) . . . . ? C1 C3 C4 O1 -137.6(3) . . . . ? C2 C3 C4 O1 96.2(3) . . . . ? C3 N C5 O1 -2.7(4) . . . . ? Pd N C5 O1 -178.7(2) . . . . ? C3 N C5 C6 176.3(3) . . . . ? Pd N C5 C6 0.3(5) . . . . ? C4 O1 C5 N -10.3(4) . . . . ? C4 O1 C5 C6 170.6(3) . . . . ? P O2 C6 C21 170.6(2) . . . . ? P O2 C6 C20 49.9(4) . . . . ? P O2 C6 C5 -69.6(3) . . . . ? N C5 C6 O2 46.8(4) . . . . ? O1 C5 C6 O2 -134.2(3) . . . . ? N C5 C6 C21 161.2(3) . . . . ? O1 C5 C6 C21 -19.7(4) . . . . ? N C5 C6 C20 -74.4(4) . . . . ? O1 C5 C6 C20 104.6(3) . . . . ? P O3 C8 C9 140.2(3) . . . . ? P O3 C8 C13 -41.6(4) . . . . ? C13 C8 C9 C10 0.9(6) . . . . ? O3 C8 C9 C10 179.1(3) . . . . ? C8 C9 C10 C11 -1.4(6) . . . . ? C9 C10 C11 C12 1.5(7) . . . . ? C10 C11 C12 C13 -1.0(7) . . . . ? C9 C8 C13 C12 -0.5(5) . . . . ? O3 C8 C13 C12 -178.6(3) . . . . ? C9 C8 C13 C14 -178.4(3) . . . . ? O3 C8 C13 C14 3.5(5) . . . . ? C11 C12 C13 C8 0.5(5) . . . . ? C11 C12 C13 C14 178.4(4) . . . . ? C8 C13 C14 C15 -164.9(3) . . . . ? C12 C13 C14 C15 17.3(5) . . . . ? C8 C13 C14 C19 17.3(5) . . . . ? C12 C13 C14 C19 -160.5(3) . . . . ? C19 C14 C15 C16 2.3(5) . . . . ? C13 C14 C15 C16 -175.6(3) . . . . ? C14 C15 C16 C17 -2.1(6) . . . . ? C15 C16 C17 C18 -0.1(6) . . . . ? C16 C17 C18 C19 2.1(5) . . . . ? C17 C18 C19 C14 -1.9(5) . . . . ? C17 C18 C19 P 176.4(3) . . . . ? C15 C14 C19 C18 -0.2(5) . . . . ? C13 C14 C19 C18 177.6(3) . . . . ? C15 C14 C19 P -178.6(3) . . . . ? C13 C14 C19 P -0.7(4) . . . . ? O2 P C19 C18 -101.0(3) . . . . ? O3 P C19 C18 153.0(3) . . . . ? Pd P C19 C18 24.3(3) . . . . ? O2 P C19 C14 77.4(3) . . . . ? O3 P C19 C14 -28.6(3) . . . . ? Pd P C19 C14 -157.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.640 _refine_diff_density_min -1.312 _refine_diff_density_rms 0.168 data_welt25 _database_code_depnum_ccdc_archive 'CCDC 627977' _audit_creation_date 22-1-05 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N O4 P Pd, C F3 O3 S' _chemical_formula_sum 'C22 H27 F3 N O7 P Pd S' _chemical_formula_weight 643.88 _chemical_absolute_configuration . 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' N N 0.0061 0.0033 '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' Pd Pd -0.9988 1.0072 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall 'C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.5110(5) _cell_length_b 10.4110(2) _cell_length_c 20.7470(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.1600(8) _cell_angle_gamma 90.00 _cell_volume 5287.07(19) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9522 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2608 _exptl_absorpt_coefficient_mu 0.904 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18463 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 30.06 _reflns_number_total 7756 _reflns_number_gt 5419 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1000P)^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 7756 _refine_ls_number_parameters 332 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1441 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_restrained_S_all 0.878 _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 Pd Pd 0.108278(9) 0.84895(2) 0.040327(12) 0.02655(9) Uani 1 1 d . . . S S 0.08283(4) 1.60838(9) -0.36165(5) 0.0371(2) Uani 1 1 d . . . P P 0.16295(3) 0.97937(7) 0.02607(4) 0.02537(17) Uani 1 1 d . . . F1 F 0.02697(13) 1.5003(3) -0.3034(2) 0.0950(11) Uani 1 1 d . . . F2 F 0.10660(12) 1.5592(3) -0.22763(13) 0.0769(8) Uani 1 1 d . . . F3 F 0.04369(10) 1.6984(2) -0.27737(13) 0.0608(7) Uani 1 1 d . . . O1 O 0.18722(10) 1.0243(2) 0.25045(12) 0.0370(5) Uani 1 1 d . . . O2 O 0.20811(8) 1.03803(19) 0.10074(11) 0.0287(5) Uani 1 1 d . . . O3 O 0.19727(9) 0.91464(19) -0.01040(12) 0.0309(5) Uani 1 1 d . . . O4 O 0.05193(9) 0.7154(2) 0.04634(13) 0.0356(5) Uani 1 1 d D . . O5 O 0.12288(13) 1.7076(3) -0.33666(18) 0.0605(8) Uani 1 1 d . . . O6 O 0.03217(14) 1.6395(4) -0.42203(17) 0.0912(14) Uani 1 1 d . . . O7 O 0.10393(10) 1.4835(2) -0.36609(14) 0.0453(6) Uani 1 1 d . . . N N 0.13311(10) 0.9180(2) 0.14898(13) 0.0281(5) Uani 1 1 d . . . C1 C 0.08958(18) 0.8039(4) 0.2134(2) 0.0510(10) Uani 1 1 d . . . H1A H 0.0657 0.7513 0.1717 0.076 Uiso 1 1 calc . . . H1B H 0.0725 0.8158 0.2454 0.076 Uiso 1 1 calc . . . H1C H 0.1248 0.7606 0.2400 0.076 Uiso 1 1 calc . . . C2 C 0.04478(15) 0.9974(4) 0.1364(2) 0.0466(9) Uani 1 1 d . . . H2A H 0.0521 1.0774 0.1175 0.070 Uiso 1 1 calc . . . H2B H 0.0238 1.0163 0.1629 0.070 Uiso 1 1 calc . . . H2C H 0.0237 0.9392 0.0961 0.070 Uiso 1 1 calc . . . C3 C 0.09840(13) 0.9344(3) 0.18709(18) 0.0324(7) Uani 1 1 d . . . C4 C 0.13425(15) 1.0211(3) 0.25072(19) 0.0387(8) Uani 1 1 d . . . H4A H 0.1185 1.1085 0.2441 0.046 Uiso 1 1 calc . . . H4B H 0.1378 0.9854 0.2969 0.046 Uiso 1 1 calc . . . C5 C 0.17961(13) 0.9691(3) 0.18852(16) 0.0287(6) Uani 1 1 d . . . C6 C 0.22778(12) 0.9747(3) 0.17186(16) 0.0290(7) Uani 1 1 d . . . C7 C 0.08565(14) 0.7904(4) -0.06359(18) 0.0404(8) Uani 1 1 d . . . H7A H 0.1100 0.7214 -0.0633 0.061 Uiso 1 1 calc . . . H7B H 0.0882 0.8630 -0.0920 0.061 Uiso 1 1 calc . . . H7C H 0.0479 0.7588 -0.0853 0.061 Uiso 1 1 calc . . . C8 C 0.22826(13) 0.9872(3) -0.03560(17) 0.0292(6) Uani 1 1 d . . . C9 C 0.27241(14) 0.9242(3) -0.03599(19) 0.0351(7) Uani 1 1 d . . . H9 H 0.2813 0.8392 -0.0177 0.042 Uiso 1 1 calc . . . C10 C 0.30321(14) 0.9863(3) -0.0631(2) 0.0391(8) Uani 1 1 d . . . H10 H 0.3335 0.9440 -0.0642 0.047 Uiso 1 1 calc . . . C12 C 0.24613(14) 1.1715(3) -0.08764(18) 0.0315(7) Uani 1 1 d . . . H12 H 0.2380 1.2572 -0.1050 0.038 Uiso 1 1 calc . . . C13 C 0.21325(13) 1.1123(3) -0.06183(16) 0.0278(6) Uani 1 1 d . . . C14 C 0.16474(13) 1.1761(3) -0.06239(16) 0.0269(6) Uani 1 1 d . . . C15 C 0.14445(15) 1.2929(3) -0.09887(18) 0.0369(8) Uani 1 1 d . . . H15 H 0.1618 1.3319 -0.1243 0.044 Uiso 1 1 calc . . . C16 C 0.10011(17) 1.3513(3) -0.0983(2) 0.0419(9) Uani 1 1 d . . . H16 H 0.0869 1.4293 -0.1242 0.050 Uiso 1 1 calc . . . C17 C 0.07404(14) 1.2987(4) -0.0608(2) 0.0414(8) Uani 1 1 d . . . H17 H 0.0438 1.3412 -0.0599 0.050 Uiso 1 1 calc . . . C18 C 0.09285(13) 1.1838(3) -0.02498(18) 0.0334(7) Uani 1 1 d . . . H18 H 0.0750 1.1458 0.0001 0.040 Uiso 1 1 calc . . . C19 C 0.13783(12) 1.1229(3) -0.02530(16) 0.0272(6) Uani 1 1 d . . . C20 C 0.24981(15) 0.8421(3) 0.1702(2) 0.0389(8) Uani 1 1 d . . . H20A H 0.2204 0.7884 0.1351 0.058 Uiso 1 1 calc . . . H20B H 0.2642 0.8032 0.2184 0.058 Uiso 1 1 calc . . . H20C H 0.2791 0.8490 0.1560 0.058 Uiso 1 1 calc . . . C21 C 0.27273(14) 1.0631(3) 0.22343(18) 0.0380(8) Uani 1 1 d . . . H21A H 0.3025 1.0659 0.2098 0.057 Uiso 1 1 calc . . . H21B H 0.2867 1.0306 0.2730 0.057 Uiso 1 1 calc . . . H21C H 0.2580 1.1497 0.2206 0.057 Uiso 1 1 calc . . . C22 C 0.06385(15) 1.5912(4) -0.2891(2) 0.0419(8) Uani 1 1 d . . . C11 C 0.28992(14) 1.1110(4) -0.08909(19) 0.0376(8) Uani 1 1 d . . . H11 H 0.3111 1.1544 -0.1078 0.045 Uiso 1 1 calc . . . H1O H 0.065(2) 0.646(3) 0.069(3) 0.086(13) Uiso 1 1 d D . . H2O H 0.0286(17) 0.691(5) 0.0044(12) 0.086(13) Uiso 1 1 d D . . 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 Pd 0.02432(14) 0.02811(15) 0.02590(15) 0.00125(9) 0.01031(10) -0.00681(8) S 0.0340(4) 0.0455(5) 0.0316(4) 0.0022(4) 0.0149(4) 0.0132(4) P 0.0246(4) 0.0263(4) 0.0255(4) 0.0011(3) 0.0118(3) -0.0054(3) F1 0.096(2) 0.085(2) 0.147(3) -0.038(2) 0.093(2) -0.0454(17) F2 0.0753(18) 0.117(2) 0.0438(14) 0.0227(15) 0.0316(14) 0.0254(17) F3 0.0730(17) 0.0603(14) 0.0702(17) -0.0067(13) 0.0510(15) 0.0112(13) O1 0.0370(13) 0.0443(13) 0.0272(12) -0.0057(10) 0.0124(10) -0.0014(10) O2 0.0258(11) 0.0284(10) 0.0269(11) 0.0028(8) 0.0077(9) -0.0065(8) O3 0.0347(12) 0.0241(11) 0.0404(13) 0.0010(9) 0.0229(10) -0.0050(9) O4 0.0295(12) 0.0371(13) 0.0353(13) 0.0027(10) 0.0106(10) -0.0128(10) O5 0.081(2) 0.0449(16) 0.087(2) -0.0074(15) 0.0658(19) -0.0088(15) O6 0.059(2) 0.165(4) 0.0360(17) 0.0120(18) 0.0103(16) 0.063(2) O7 0.0394(14) 0.0438(14) 0.0527(16) -0.0122(12) 0.0211(13) 0.0055(11) N 0.0283(13) 0.0290(13) 0.0258(13) 0.0040(10) 0.0114(11) -0.0007(10) C1 0.074(3) 0.042(2) 0.057(2) 0.0094(19) 0.048(2) -0.005(2) C2 0.0323(18) 0.054(2) 0.050(2) -0.0027(18) 0.0156(17) 0.0007(16) C3 0.0340(17) 0.0339(16) 0.0350(17) 0.0031(13) 0.0207(14) 0.0002(13) C4 0.0392(19) 0.046(2) 0.0333(18) -0.0009(15) 0.0187(15) 0.0035(15) C5 0.0323(16) 0.0253(14) 0.0262(15) 0.0083(12) 0.0115(13) 0.0017(12) C6 0.0241(15) 0.0317(15) 0.0245(15) 0.0056(12) 0.0054(12) -0.0026(12) C7 0.0363(18) 0.051(2) 0.0329(18) -0.0110(16) 0.0151(15) -0.0191(16) C8 0.0286(15) 0.0330(16) 0.0284(15) -0.0038(12) 0.0151(13) -0.0088(12) C9 0.0401(19) 0.0283(16) 0.0431(19) -0.0015(14) 0.0245(16) -0.0016(13) C10 0.0386(19) 0.0432(19) 0.044(2) -0.0124(16) 0.0266(17) -0.0078(15) C12 0.0370(18) 0.0321(16) 0.0289(16) -0.0036(13) 0.0181(14) -0.0099(13) C13 0.0291(16) 0.0287(15) 0.0253(15) -0.0038(12) 0.0120(13) -0.0071(12) C14 0.0292(15) 0.0306(15) 0.0229(14) -0.0029(12) 0.0135(12) -0.0074(12) C15 0.0425(19) 0.0348(18) 0.0367(18) 0.0059(15) 0.0209(15) -0.0013(15) C16 0.043(2) 0.043(2) 0.042(2) 0.0139(15) 0.0211(18) 0.0074(15) C17 0.0316(18) 0.048(2) 0.047(2) 0.0119(17) 0.0197(16) 0.0049(15) C18 0.0269(16) 0.0416(17) 0.0336(17) 0.0065(14) 0.0155(14) 0.0004(13) C19 0.0256(15) 0.0293(14) 0.0233(15) -0.0004(12) 0.0082(12) -0.0062(12) C20 0.0362(19) 0.0327(17) 0.047(2) 0.0093(14) 0.0187(17) 0.0023(13) C21 0.0293(16) 0.0425(19) 0.0345(18) 0.0034(15) 0.0080(14) -0.0059(14) C22 0.0378(19) 0.047(2) 0.049(2) -0.0008(17) 0.0264(17) 0.0001(16) C11 0.0380(19) 0.0443(18) 0.0392(19) -0.0072(16) 0.0252(16) -0.0115(15) _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 Pd C7 2.045(3) . y Pd O4 2.128(2) . y Pd P 2.1447(8) . y Pd N 2.158(3) . y S O6 1.422(3) . ? S O5 1.424(3) . ? S O7 1.444(2) . ? S C22 1.813(4) . ? P O2 1.600(2) . y P O3 1.603(2) . ? P C19 1.782(3) . ? F1 C22 1.319(4) . ? F2 C22 1.323(4) . ? F3 C22 1.317(4) . ? O1 C5 1.334(4) . ? O1 C4 1.460(4) . ? O2 C6 1.475(3) . y O3 C8 1.406(4) . ? O4 H1O 0.85(4) . ? O4 H2O 0.85(3) . ? N C5 1.278(4) . y N C3 1.502(4) . ? C1 C3 1.525(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.515(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.531(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.516(4) . y C6 C20 1.514(4) . ? C6 C21 1.521(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.383(5) . ? C8 C13 1.399(4) . ? C9 C10 1.374(5) . ? C9 H9 0.9500 . ? C10 C11 1.389(5) . ? C10 H10 0.9500 . ? C12 C11 1.372(5) . ? C12 C13 1.388(4) . ? C12 H12 0.9500 . ? C13 C14 1.486(5) . ? C14 C19 1.402(4) . ? C14 C15 1.406(5) . ? C15 C16 1.367(5) . ? C15 H15 0.9500 . ? C16 C17 1.389(5) . ? C16 H16 0.9500 . ? C17 C18 1.379(5) . ? C17 H17 0.9500 . ? C18 C19 1.393(5) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C11 H11 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 C7 Pd O4 89.30(12) . . y C7 Pd P 86.47(10) . . y O4 Pd P 175.76(7) . . y C7 Pd N 177.73(12) . . y O4 Pd N 92.76(10) . . y P Pd N 91.47(7) . . y O6 S O5 116.1(2) . . ? O6 S O7 114.2(2) . . ? O5 S O7 114.19(17) . . ? O6 S C22 102.5(2) . . ? O5 S C22 103.74(18) . . ? O7 S C22 103.92(17) . . ? O2 P O3 104.67(12) . . ? O2 P C19 100.18(12) . . ? O3 P C19 102.80(14) . . ? O2 P Pd 113.05(9) . . ? O3 P Pd 113.59(8) . . ? C19 P Pd 120.57(11) . . ? C5 O1 C4 106.0(2) . . ? C6 O2 P 124.47(17) . . ? C8 O3 P 122.50(19) . . ? Pd O4 H1O 117(4) . . ? Pd O4 H2O 111(4) . . ? H1O O4 H2O 104(5) . . ? C5 N C3 107.8(3) . . ? C5 N Pd 123.8(2) . . ? C3 N Pd 127.84(19) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N C3 C2 109.6(3) . . ? N C3 C1 109.3(3) . . ? C2 C3 C1 111.8(3) . . ? N C3 C4 102.0(3) . . ? C2 C3 C4 112.5(3) . . ? C1 C3 C4 111.2(3) . . ? O1 C4 C3 105.2(3) . . ? O1 C4 H4A 110.7 . . ? C3 C4 H4A 110.7 . . ? O1 C4 H4B 110.7 . . ? C3 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? N C5 O1 118.0(3) . . ? N C5 C6 126.3(3) . . ? O1 C5 C6 115.7(3) . . ? O2 C6 C20 110.7(3) . . ? O2 C6 C5 106.6(2) . . ? C20 C6 C5 111.8(3) . . ? O2 C6 C21 104.0(2) . . ? C20 C6 C21 111.2(3) . . ? C5 C6 C21 112.2(3) . . ? Pd C7 H7A 109.5 . . ? Pd C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Pd C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 122.9(3) . . ? C9 C8 O3 115.5(3) . . ? C13 C8 O3 121.5(3) . . ? C10 C9 C8 119.1(3) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 119.7(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C11 C12 C13 122.5(3) . . ? C11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C8 115.8(3) . . ? C12 C13 C14 122.6(3) . . ? C8 C13 C14 121.6(3) . . ? C19 C14 C15 117.2(3) . . ? C19 C14 C13 121.1(3) . . ? C15 C14 C13 121.7(3) . . ? C16 C15 C14 121.1(3) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 121.3(3) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 118.8(3) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C17 C18 C19 120.5(3) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C14 121.0(3) . . ? C18 C19 P 118.8(2) . . ? C14 C19 P 120.1(2) . . ? C6 C20 H20A 109.5 . . ? C6 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C6 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C6 C21 H21A 109.5 . . ? C6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? F3 C22 F1 107.7(3) . . ? F3 C22 F2 107.4(3) . . ? F1 C22 F2 106.8(4) . . ? F3 C22 S 112.0(3) . . ? F1 C22 S 111.6(3) . . ? F2 C22 S 111.0(3) . . ? C12 C11 C10 119.9(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.889 _refine_diff_density_min -1.209 _refine_diff_density_rms 0.137 data_compound14a _database_code_depnum_ccdc_archive 'CCDC 627978' _audit_creation_date 22-1-05 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H25 N O4 P Pd, C F3 S O3' _chemical_formula_sum 'C23 H25 F3 N O7 P Pd S' _chemical_formula_weight 653.87 _chemical_absolute_configuration . 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' 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.6170(5) _cell_length_b 12.4040(6) _cell_length_c 11.6760(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.5330(17) _cell_angle_gamma 90.00 _cell_volume 2610.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6211 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.917 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13289 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0987 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 30.49 _reflns_number_total 7710 _reflns_number_gt 3858 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0500P)^2^+10.0000P] 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 7710 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1534 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.1823 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd Pd 0.20932(2) 0.05413(4) -0.12510(4) 0.04971(16) Uani 1 1 d . . . S S 0.21420(13) 0.04114(16) 0.3300(2) 0.0806(6) Uani 1 1 d . . . P P 0.29500(9) -0.03135(12) -0.18183(14) 0.0496(4) Uani 1 1 d . . . F2 F 0.1864(4) -0.1625(4) 0.3309(7) 0.154(3) Uani 1 1 d . . . F3 F 0.2659(7) -0.1178(6) 0.2379(10) 0.235(5) Uani 1 1 d . . . F1 F 0.2878(6) -0.1189(9) 0.4038(15) 0.287(8) Uani 1 1 d . . . O1 O 0.0718(3) -0.1534(4) -0.3743(5) 0.0857(15) Uani 1 1 d . . . O2 O 0.2649(2) -0.1269(3) -0.2709(3) 0.0574(10) Uani 1 1 d . . . O3 O 0.3424(2) 0.0458(3) -0.2450(4) 0.0606(11) Uani 1 1 d . . . O4 O 0.1418(2) 0.1518(4) -0.0451(4) 0.0627(11) Uani 1 1 d . . . O5 O 0.2744(4) 0.0998(5) 0.3191(8) 0.130(3) Uani 1 1 d . . . O6 O 0.1723(5) 0.0466(6) 0.4092(8) 0.154(3) Uani 1 1 d . . . O7 O 0.1572(5) 0.0552(9) 0.2150(9) 0.209(5) Uani 1 1 d . . . N N 0.1234(3) -0.0423(4) -0.2301(5) 0.0555(12) Uani 1 1 d . . . C1 C 0.0455(6) -0.0954(8) -0.1011(9) 0.112(3) Uani 1 1 d . . . H1A H 0.0806 -0.1555 -0.0820 0.168 Uiso 1 1 calc . . . H1B H -0.0045 -0.1208 -0.1019 0.168 Uiso 1 1 calc . . . H1C H 0.0602 -0.0386 -0.0414 0.168 Uiso 1 1 calc . . . C2 C 0.0090(4) 0.0588(7) -0.2411(10) 0.100(3) Uani 1 1 d . . . H2A H 0.0323 0.1073 -0.1761 0.151 Uiso 1 1 calc . . . H2B H -0.0439 0.0517 -0.2448 0.151 Uiso 1 1 calc . . . H2C H 0.0150 0.0884 -0.3160 0.151 Uiso 1 1 calc . . . C3 C 0.0457(4) -0.0512(6) -0.2202(7) 0.0704(19) Uani 1 1 d . . . C4 C 0.0123(5) -0.1282(8) -0.3179(9) 0.111(3) Uani 1 1 d . . . H4A H -0.0053 -0.1942 -0.2859 0.133 Uiso 1 1 calc . . . H4B H -0.0301 -0.0944 -0.3752 0.133 Uiso 1 1 calc . . . C5 C 0.1308(4) -0.0998(5) -0.3148(6) 0.0605(16) Uani 1 1 d . . . C6 C 0.1982(4) -0.1169(6) -0.3602(6) 0.0694(19) Uani 1 1 d . . . H6A H 0.1911 -0.1829 -0.4094 0.083 Uiso 1 1 calc . . . H6B H 0.2031 -0.0554 -0.4119 0.083 Uiso 1 1 calc . . . C7 C 0.2894(4) 0.1489(6) -0.0292(8) 0.088(3) Uani 1 1 d . . . H7A H 0.3315 0.1044 0.0151 0.105 Uiso 1 1 calc . . . H7B H 0.3080 0.1985 -0.0817 0.105 Uiso 1 1 calc . . . C8 C 0.4120(3) 0.0184(5) -0.2621(5) 0.0530(14) Uani 1 1 d . . . C9 C 0.4323(4) 0.0729(5) -0.3511(6) 0.0675(18) Uani 1 1 d . . . H9 H 0.3986 0.1214 -0.4000 0.081 Uiso 1 1 calc . . . C10 C 0.5019(5) 0.0570(6) -0.3694(7) 0.078(2) Uani 1 1 d . . . H10 H 0.5171 0.0960 -0.4293 0.093 Uiso 1 1 calc . . . C11 C 0.5480(4) -0.0144(7) -0.3016(7) 0.074(2) Uani 1 1 d . . . H11 H 0.5954 -0.0273 -0.3154 0.089 Uiso 1 1 calc . . . C12 C 0.5274(4) -0.0684(5) -0.2132(6) 0.0639(17) Uani 1 1 d . . . H12 H 0.5612 -0.1177 -0.1658 0.077 Uiso 1 1 calc . . . C13 C 0.4576(3) -0.0531(4) -0.1903(5) 0.0475(13) Uani 1 1 d . . . C14 C 0.4362(3) -0.1069(4) -0.0909(5) 0.0475(13) Uani 1 1 d . . . C15 C 0.4868(4) -0.1632(5) -0.0049(6) 0.0633(17) Uani 1 1 d . . . H15 H 0.5370 -0.1680 -0.0092 0.076 Uiso 1 1 calc . . . C16 C 0.4656(5) -0.2117(5) 0.0857(6) 0.073(2) Uani 1 1 d . . . H16 H 0.5016 -0.2508 0.1426 0.088 Uiso 1 1 calc . . . C17 C 0.3950(5) -0.2063(6) 0.0979(6) 0.074(2) Uani 1 1 d . . . H17 H 0.3817 -0.2410 0.1622 0.089 Uiso 1 1 calc . . . C18 C 0.3437(4) -0.1502(5) 0.0159(6) 0.0656(17) Uani 1 1 d . . . H18 H 0.2942 -0.1448 0.0232 0.079 Uiso 1 1 calc . . . C19 C 0.3638(3) -0.1010(4) -0.0780(5) 0.0492(14) Uani 1 1 d . . . C20 C 0.2262(9) -0.0954(8) 0.3020(18) 0.165(7) Uani 1 1 d . . . C21 C 0.2573(4) 0.2111(6) 0.0542(6) 0.0694(18) Uani 1 1 d . . . H21A H 0.2781 0.1824 0.1348 0.083 Uiso 1 1 calc . . . H21B H 0.2740 0.2868 0.0538 0.083 Uiso 1 1 calc . . . C22 C 0.1766(4) 0.2109(5) 0.0317(5) 0.0552(15) Uani 1 1 d . . . C23 C 0.1372(4) 0.2818(5) 0.0982(7) 0.074(2) Uani 1 1 d . . . H23A H 0.0838 0.2800 0.0609 0.111 Uiso 1 1 calc . . . H23B H 0.1555 0.3558 0.0976 0.111 Uiso 1 1 calc . . . H23C H 0.1462 0.2564 0.1801 0.111 Uiso 1 1 calc . . . 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 Pd 0.0457(3) 0.0488(3) 0.0553(3) -0.0072(2) 0.01385(19) 0.0004(2) S 0.1051(16) 0.0626(11) 0.0868(14) 0.0025(10) 0.0475(13) 0.0046(11) P 0.0527(9) 0.0467(8) 0.0526(9) 0.0037(7) 0.0193(7) 0.0056(6) F2 0.189(7) 0.073(3) 0.238(7) -0.009(4) 0.128(6) -0.035(4) F3 0.411(14) 0.112(5) 0.290(11) -0.061(6) 0.286(11) -0.036(7) F1 0.174(9) 0.180(9) 0.50(2) 0.125(12) 0.080(12) 0.072(8) O1 0.078(3) 0.087(4) 0.082(3) -0.033(3) 0.001(3) -0.007(3) O2 0.064(3) 0.058(2) 0.049(2) -0.007(2) 0.013(2) 0.011(2) O3 0.062(3) 0.054(2) 0.074(3) 0.021(2) 0.033(2) 0.013(2) O4 0.050(2) 0.068(3) 0.070(3) -0.022(2) 0.013(2) 0.002(2) O5 0.100(5) 0.081(4) 0.215(8) -0.006(5) 0.053(5) -0.013(4) O6 0.201(9) 0.119(6) 0.179(8) -0.032(5) 0.117(7) 0.016(5) O7 0.134(7) 0.262(12) 0.200(9) 0.129(9) -0.015(7) -0.027(7) N 0.052(3) 0.054(3) 0.059(3) -0.008(3) 0.012(2) -0.006(2) C1 0.108(7) 0.122(7) 0.123(8) 0.002(6) 0.060(6) -0.036(6) C2 0.051(4) 0.084(5) 0.154(8) -0.016(6) 0.003(5) 0.001(4) C3 0.055(4) 0.064(4) 0.095(5) -0.014(4) 0.023(4) -0.016(3) C4 0.074(6) 0.110(7) 0.145(8) -0.061(6) 0.019(6) -0.031(5) C5 0.062(4) 0.058(4) 0.057(4) -0.005(3) 0.008(3) 0.002(3) C6 0.084(5) 0.077(5) 0.044(4) -0.006(3) 0.008(3) 0.010(4) C7 0.051(4) 0.086(5) 0.118(7) -0.047(5) 0.006(4) -0.007(4) C8 0.055(4) 0.052(3) 0.057(4) 0.001(3) 0.023(3) 0.001(3) C9 0.080(5) 0.065(4) 0.064(4) 0.005(3) 0.031(4) -0.001(3) C10 0.097(6) 0.075(5) 0.075(5) -0.009(4) 0.048(5) -0.018(4) C11 0.064(5) 0.085(5) 0.084(5) -0.023(4) 0.039(4) -0.017(4) C12 0.054(4) 0.066(4) 0.072(4) -0.020(3) 0.016(3) -0.004(3) C13 0.051(3) 0.041(3) 0.053(3) -0.011(3) 0.019(3) -0.005(3) C14 0.055(3) 0.035(3) 0.049(3) -0.003(2) 0.007(3) 0.005(2) C15 0.060(4) 0.050(3) 0.074(4) -0.006(3) 0.005(3) 0.009(3) C16 0.090(6) 0.053(4) 0.066(5) 0.012(3) 0.001(4) 0.011(4) C17 0.108(6) 0.056(4) 0.060(4) 0.014(3) 0.024(4) 0.002(4) C18 0.077(5) 0.061(4) 0.063(4) 0.017(3) 0.025(4) 0.005(3) C19 0.061(4) 0.040(3) 0.047(3) 0.003(3) 0.013(3) 0.002(3) C20 0.200(14) 0.069(6) 0.303(19) 0.017(9) 0.204(15) 0.032(8) C21 0.067(4) 0.073(4) 0.064(4) -0.013(4) 0.009(3) -0.012(4) C22 0.067(4) 0.047(3) 0.051(4) -0.003(3) 0.015(3) -0.001(3) C23 0.099(6) 0.054(4) 0.075(5) -0.016(4) 0.032(4) 0.003(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 Pd C7 2.006(7) . y Pd N 2.123(5) . y Pd O4 2.124(4) . y Pd P 2.1535(15) . y S O6 1.353(7) . ? S O5 1.368(6) . ? S O7 1.497(9) . ? S C20 1.749(10) . ? P O2 1.584(4) . y P O3 1.601(4) . ? P C19 1.754(6) . ? F2 C20 1.217(11) . ? F3 C20 1.209(10) . ? F1 C20 1.46(2) . ? O1 C5 1.322(8) . ? O1 C4 1.457(10) . ? O2 C6 1.413(8) . y O3 C8 1.403(7) . ? O4 C22 1.213(7) . Y N C5 1.256(8) . y N C3 1.483(8) . ? C1 C3 1.495(12) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.518(10) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.498(10) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.495(10) . y C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C21 1.481(10) . y C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.360(8) . ? C8 C9 1.369(8) . ? C9 C10 1.380(10) . ? C9 H9 0.9500 . ? C10 C11 1.343(11) . ? C10 H10 0.9500 . ? C11 C12 1.365(10) . ? C11 H11 0.9500 . ? C12 C13 1.404(8) . ? C12 H12 0.9500 . ? C13 C14 1.478(8) . ? C14 C15 1.382(8) . ? C14 C19 1.396(8) . ? C15 C16 1.359(10) . ? C15 H15 0.9500 . ? C16 C17 1.360(10) . ? C16 H16 0.9500 . ? C17 C18 1.361(9) . ? C17 H17 0.9500 . ? C18 C19 1.385(8) . ? C18 H18 0.9500 . ? C21 C22 1.458(9) . y C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.484(9) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C7 Pd N 178.3(3) . . y C7 Pd O4 81.9(2) . . y N Pd O4 97.54(18) . . y C7 Pd P 87.5(2) . . y N Pd P 93.12(14) . . y O4 Pd P 169.16(12) . . y O6 S O5 131.5(5) . . ? O6 S O7 101.9(6) . . ? O5 S O7 105.5(5) . . ? O6 S C20 107.4(5) . . ? O5 S C20 110.6(5) . . ? O7 S C20 92.3(9) . . ? O2 P O3 106.9(2) . . ? O2 P C19 99.3(2) . . ? O3 P C19 102.8(3) . . ? O2 P Pd 113.78(17) . . ? O3 P Pd 112.56(16) . . ? C19 P Pd 119.9(2) . . ? C5 O1 C4 106.2(5) . . ? C6 O2 P 121.3(4) . . ? C8 O3 P 123.9(4) . . ? C22 O4 Pd 113.8(4) . . ? C5 N C3 108.7(5) . . ? C5 N Pd 124.0(5) . . ? C3 N Pd 127.3(4) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N C3 C1 109.3(7) . . ? N C3 C4 102.4(6) . . ? C1 C3 C4 112.2(7) . . ? N C3 C2 109.1(6) . . ? C1 C3 C2 111.9(8) . . ? C4 C3 C2 111.5(7) . . ? O1 C4 C3 105.3(6) . . ? O1 C4 H4A 110.7 . . ? C3 C4 H4A 110.7 . . ? O1 C4 H4B 110.7 . . ? C3 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? N C5 O1 117.3(6) . . ? N C5 C6 128.9(6) . . ? O1 C5 C6 113.8(6) . . ? O2 C6 C5 114.3(5) . . ? O2 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? O2 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C21 C7 Pd 107.8(5) . . ? C21 C7 H7A 110.1 . . ? Pd C7 H7A 110.1 . . ? C21 C7 H7B 110.1 . . ? Pd C7 H7B 110.1 . . ? H7A C7 H7B 108.5 . . ? C13 C8 C9 122.8(6) . . ? C13 C8 O3 121.7(5) . . ? C9 C8 O3 115.4(6) . . ? C8 C9 C10 119.7(7) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 119.3(7) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 120.6(7) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 121.8(7) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C8 C13 C12 115.7(6) . . ? C8 C13 C14 122.0(5) . . ? C12 C13 C14 122.2(6) . . ? C15 C14 C19 116.7(6) . . ? C15 C14 C13 122.0(6) . . ? C19 C14 C13 121.3(5) . . ? C16 C15 C14 120.7(6) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 122.5(6) . . ? C15 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C16 C17 C18 118.5(6) . . ? C16 C17 H17 120.8 . . ? C18 C17 H17 120.8 . . ? C17 C18 C19 120.1(7) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C14 121.5(6) . . ? C18 C19 P 118.0(5) . . ? C14 C19 P 120.5(4) . . ? F3 C20 F2 121.5(11) . . ? F3 C20 F1 88.9(12) . . ? F2 C20 F1 92.7(12) . . ? F3 C20 S 117.7(9) . . ? F2 C20 S 119.7(7) . . ? F1 C20 S 98.8(12) . . ? C22 C21 C7 116.6(6) . . ? C22 C21 H21A 108.1 . . ? C7 C21 H21A 108.1 . . ? C22 C21 H21B 108.1 . . ? C7 C21 H21B 108.1 . . ? H21A C21 H21B 107.3 . . ? O4 C22 C21 118.1(6) . . ? O4 C22 C23 120.2(6) . . ? C21 C22 C23 121.8(6) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C7 Pd P O2 -179.3(3) . . . . ? N Pd P O2 -0.9(2) . . . . ? O4 Pd P O2 168.4(7) . . . . ? C7 Pd P O3 -57.6(3) . . . . ? N Pd P O3 120.8(2) . . . . ? O4 Pd P O3 -69.9(7) . . . . ? C7 Pd P C19 63.5(4) . . . . ? N Pd P C19 -118.1(3) . . . . ? O4 Pd P C19 51.2(8) . . . . ? O3 P O2 C6 -85.8(5) . . . . ? C19 P O2 C6 167.6(5) . . . . ? Pd P O2 C6 39.0(5) . . . . ? O2 P O3 C8 -71.7(5) . . . . ? C19 P O3 C8 32.3(5) . . . . ? Pd P O3 C8 162.7(4) . . . . ? C7 Pd O4 C22 -8.6(5) . . . . ? N Pd O4 C22 173.0(4) . . . . ? P Pd O4 C22 3.8(10) . . . . ? C7 Pd N C5 93(9) . . . . ? O4 Pd N C5 164.4(5) . . . . ? P Pd N C5 -17.6(5) . . . . ? C7 Pd N C3 -85(9) . . . . ? O4 Pd N C3 -13.4(6) . . . . ? P Pd N C3 164.5(5) . . . . ? C5 N C3 C1 119.9(7) . . . . ? Pd N C3 C1 -62.0(8) . . . . ? C5 N C3 C4 0.8(8) . . . . ? Pd N C3 C4 178.9(5) . . . . ? C5 N C3 C2 -117.5(7) . . . . ? Pd N C3 C2 60.6(8) . . . . ? C5 O1 C4 C3 1.1(9) . . . . ? N C3 C4 O1 -1.1(9) . . . . ? C1 C3 C4 O1 -118.2(8) . . . . ? C2 C3 C4 O1 115.5(8) . . . . ? C3 N C5 O1 0.0(8) . . . . ? Pd N C5 O1 -178.2(4) . . . . ? C3 N C5 C6 179.6(7) . . . . ? Pd N C5 C6 1.4(10) . . . . ? C4 O1 C5 N -0.7(9) . . . . ? C4 O1 C5 C6 179.6(7) . . . . ? P O2 C6 C5 -62.3(7) . . . . ? N C5 C6 O2 40.4(10) . . . . ? O1 C5 C6 O2 -139.9(6) . . . . ? N Pd C7 C21 83(9) . . . . ? O4 Pd C7 C21 11.2(5) . . . . ? P Pd C7 C21 -166.5(6) . . . . ? P O3 C8 C13 -25.9(8) . . . . ? P O3 C8 C9 157.6(5) . . . . ? C13 C8 C9 C10 -0.9(11) . . . . ? O3 C8 C9 C10 175.5(6) . . . . ? C8 C9 C10 C11 2.0(11) . . . . ? C9 C10 C11 C12 -1.9(12) . . . . ? C10 C11 C12 C13 0.8(11) . . . . ? C9 C8 C13 C12 -0.2(9) . . . . ? O3 C8 C13 C12 -176.4(5) . . . . ? C9 C8 C13 C14 176.8(6) . . . . ? O3 C8 C13 C14 0.6(9) . . . . ? C11 C12 C13 C8 0.3(9) . . . . ? C11 C12 C13 C14 -176.8(6) . . . . ? C8 C13 C14 C15 -167.5(6) . . . . ? C12 C13 C14 C15 9.3(8) . . . . ? C8 C13 C14 C19 10.9(8) . . . . ? C12 C13 C14 C19 -172.2(6) . . . . ? C19 C14 C15 C16 1.3(9) . . . . ? C13 C14 C15 C16 179.8(6) . . . . ? C14 C15 C16 C17 -1.1(11) . . . . ? C15 C16 C17 C18 0.0(12) . . . . ? C16 C17 C18 C19 0.6(11) . . . . ? C17 C18 C19 C14 -0.3(10) . . . . ? C17 C18 C19 P 179.2(5) . . . . ? C15 C14 C19 C18 -0.6(9) . . . . ? C13 C14 C19 C18 -179.2(5) . . . . ? C15 C14 C19 P 179.9(4) . . . . ? C13 C14 C19 P 1.3(8) . . . . ? O2 P C19 C18 -89.5(5) . . . . ? O3 P C19 C18 160.7(5) . . . . ? Pd P C19 C18 34.9(6) . . . . ? O2 P C19 C14 90.0(5) . . . . ? O3 P C19 C14 -19.8(5) . . . . ? Pd P C19 C14 -145.6(4) . . . . ? O6 S C20 F3 -175.9(17) . . . . ? O5 S C20 F3 -27(2) . . . . ? O7 S C20 F3 80.8(19) . . . . ? O6 S C20 F2 16(2) . . . . ? O5 S C20 F2 164.8(15) . . . . ? O7 S C20 F2 -87.6(17) . . . . ? O6 S C20 F1 -82.5(9) . . . . ? O5 S C20 F1 66.7(10) . . . . ? O7 S C20 F1 174.2(8) . . . . ? Pd C7 C21 C22 -13.7(9) . . . . ? Pd O4 C22 C21 2.9(7) . . . . ? Pd O4 C22 C23 -178.2(5) . . . . ? C7 C21 C22 O4 7.5(10) . . . . ? C7 C21 C22 C23 -171.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 1.269 _refine_diff_density_min -0.808 _refine_diff_density_rms 0.175 data_welt24 _database_code_depnum_ccdc_archive 'CCDC 627979' _audit_creation_date 22-1-05 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H29 N O4 P Pd, C F3 S O3' _chemical_formula_sum 'C25 H29 F3 N O7 P Pd S' _chemical_formula_weight 681.92 _chemical_absolute_configuration . 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' N N 0.0061 0.0033 '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' Pd Pd -0.9988 1.0072 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/N' _symmetry_space_group_name_Hall '-P 2yn' 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 12.1860(10) _cell_length_b 14.6170(10) _cell_length_c 16.1040(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.62(5) _cell_angle_gamma 90.00 _cell_volume 2762.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13126 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.870 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29429 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_sigmaI/netI 0.0961 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 29.99 _reflns_number_total 8030 _reflns_number_gt 4540 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0500P)^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 8030 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 Pd Pd 0.328070(19) 0.658288(17) 0.073628(16) 0.03167(9) Uani 1 1 d . . . S S 0.22160(7) 0.89037(6) -0.14801(5) 0.0377(2) Uani 1 1 d . . . P P 0.20876(7) 0.63154(6) 0.14710(5) 0.0307(2) Uani 1 1 d . . . F1 F 0.00956(16) 0.93646(17) -0.21546(16) 0.0732(8) Uani 1 1 d . . . F2 F 0.03058(18) 0.81209(16) -0.14122(14) 0.0616(6) Uani 1 1 d . . . F3 F 0.06198(19) 0.94235(15) -0.07774(16) 0.0670(7) Uani 1 1 d . . . O1 O 0.46946(18) 0.69474(17) 0.02580(15) 0.0431(6) Uani 1 1 d . . . O2 O 0.13767(16) 0.53880(14) 0.11885(13) 0.0330(5) Uani 1 1 d . . . O3 O 0.26535(17) 0.61967(16) 0.24931(13) 0.0358(5) Uani 1 1 d . . . O4 O 0.16805(18) 0.41663(16) -0.05762(14) 0.0423(6) Uani 1 1 d . . . O5 O 0.25117(18) 0.98511(16) -0.15419(16) 0.0465(6) Uani 1 1 d . . . O6 O 0.2768(2) 0.84664(16) -0.06790(16) 0.0534(7) Uani 1 1 d . . . O7 O 0.2162(2) 0.83646(16) -0.22361(15) 0.0470(6) Uani 1 1 d . . . N1 N 0.2648(2) 0.54611(18) -0.01164(16) 0.0327(6) Uani 1 1 d . . . C1 C 0.3789(3) 0.7710(2) 0.1475(2) 0.0473(9) Uani 1 1 d . . . H1A H 0.3294 0.8237 0.1236 0.057 Uiso 1 1 calc . . . H1B H 0.3743 0.7598 0.2071 0.057 Uiso 1 1 calc . . . C2 C 0.5000(3) 0.7902(3) 0.1469(3) 0.0530(10) Uani 1 1 d . . . H2A H 0.5113 0.8573 0.1473 0.064 Uiso 1 1 calc . . . H2B H 0.5516 0.7654 0.2005 0.064 Uiso 1 1 calc . . . C3 C 0.5321(3) 0.7512(2) 0.0725(2) 0.0446(9) Uani 1 1 d . . . C4 C 0.6453(3) 0.7752(3) 0.0581(3) 0.0747(14) Uani 1 1 d . . . H4A H 0.7066 0.7503 0.1053 0.112 Uiso 1 1 calc . . . H4B H 0.6529 0.8419 0.0564 0.112 Uiso 1 1 calc . . . H4C H 0.6505 0.7490 0.0032 0.112 Uiso 1 1 calc . . . C5 C 0.2679(3) 0.5373(2) -0.10421(19) 0.0351(8) Uani 1 1 d . . . C6 C 0.2274(3) 0.6250(3) -0.1525(2) 0.0519(10) Uani 1 1 d . . . H6A H 0.1499 0.6388 -0.1494 0.078 Uiso 1 1 calc . . . H6B H 0.2277 0.6179 -0.2129 0.078 Uiso 1 1 calc . . . H6C H 0.2785 0.6752 -0.1264 0.078 Uiso 1 1 calc . . . C7 C 0.3880(3) 0.5143(3) -0.1063(2) 0.0554(11) Uani 1 1 d . . . H7A H 0.4121 0.4573 -0.0746 0.083 Uiso 1 1 calc . . . H7B H 0.4394 0.5640 -0.0795 0.083 Uiso 1 1 calc . . . H7C H 0.3904 0.5067 -0.1663 0.083 Uiso 1 1 calc . . . C8 C 0.1866(3) 0.4569(3) -0.1356(2) 0.0501(10) Uani 1 1 d . . . H8A H 0.1138 0.4786 -0.1745 0.060 Uiso 1 1 calc . . . H8B H 0.2211 0.4118 -0.1668 0.060 Uiso 1 1 calc . . . C9 C 0.2094(2) 0.4777(2) 0.0054(2) 0.0324(8) Uani 1 1 d . . . C10 C 0.1864(3) 0.4561(2) 0.0915(2) 0.0345(8) Uani 1 1 d . . . C11 C 0.2970(3) 0.4274(2) 0.1578(2) 0.0444(9) Uani 1 1 d . . . H11A H 0.2808 0.4135 0.2129 0.067 Uiso 1 1 calc . . . H11B H 0.3524 0.4774 0.1660 0.067 Uiso 1 1 calc . . . H11C H 0.3283 0.3730 0.1370 0.067 Uiso 1 1 calc . . . C12 C 0.0944(3) 0.3844(3) 0.0831(2) 0.0472(9) Uani 1 1 d . . . H12A H 0.0824 0.3724 0.1399 0.071 Uiso 1 1 calc . . . H12B H 0.1179 0.3278 0.0601 0.071 Uiso 1 1 calc . . . H12C H 0.0233 0.4066 0.0438 0.071 Uiso 1 1 calc . . . C13 C 0.0975(2) 0.7115(2) 0.14671(19) 0.0292(7) Uani 1 1 d . . . C14 C 0.0645(3) 0.7754(2) 0.0796(2) 0.0378(8) Uani 1 1 d . . . H14 H 0.1001 0.7762 0.0339 0.045 Uiso 1 1 calc . . . C15 C -0.0204(3) 0.8367(2) 0.0812(2) 0.0456(9) Uani 1 1 d . . . H15 H -0.0457 0.8788 0.0351 0.055 Uiso 1 1 calc . . . C16 C -0.0686(3) 0.8377(2) 0.1485(3) 0.0465(10) Uani 1 1 d . . . H16 H -0.1254 0.8819 0.1494 0.056 Uiso 1 1 calc . . . C17 C -0.0365(3) 0.7755(3) 0.2154(2) 0.0404(9) Uani 1 1 d . . . H17 H -0.0718 0.7769 0.2613 0.048 Uiso 1 1 calc . . . C18 C 0.0483(2) 0.7103(2) 0.2156(2) 0.0337(8) Uani 1 1 d . . . C19 C 0.0863(3) 0.6439(2) 0.2864(2) 0.0362(8) Uani 1 1 d . . . C20 C 0.1925(3) 0.6009(2) 0.3016(2) 0.0369(8) Uani 1 1 d . . . C21 C 0.2326(3) 0.5400(3) 0.3689(2) 0.0488(10) Uani 1 1 d . . . H21 H 0.3059 0.5132 0.3787 0.059 Uiso 1 1 calc . . . C22 C 0.1627(3) 0.5194(3) 0.4216(2) 0.0483(10) Uani 1 1 d . . . H22 H 0.1890 0.4792 0.4692 0.058 Uiso 1 1 calc . . . C23 C 0.0550(4) 0.5570(3) 0.4052(2) 0.0603(11) Uani 1 1 d . . . H23 H 0.0057 0.5396 0.4392 0.072 Uiso 1 1 calc . . . C24 C 0.0188(3) 0.6193(3) 0.3401(2) 0.0508(10) Uani 1 1 d . . . H24 H -0.0542 0.6464 0.3314 0.061 Uiso 1 1 calc . . . C25 C 0.0746(3) 0.8951(3) -0.1453(2) 0.0469(9) Uani 1 1 d . . . 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 Pd 0.03618(15) 0.02862(16) 0.02929(15) -0.00335(11) 0.00722(10) -0.00059(11) S 0.0438(5) 0.0347(5) 0.0327(5) 0.0006(4) 0.0068(4) 0.0035(4) P 0.0342(4) 0.0305(5) 0.0255(4) -0.0008(4) 0.0047(3) 0.0029(4) F1 0.0406(11) 0.0844(19) 0.0880(18) 0.0430(15) 0.0062(11) 0.0028(12) F2 0.0710(14) 0.0494(14) 0.0689(16) 0.0057(12) 0.0266(12) -0.0162(12) F3 0.0855(16) 0.0504(15) 0.0836(18) -0.0040(13) 0.0547(14) 0.0025(12) O1 0.0420(13) 0.0407(15) 0.0487(15) -0.0003(13) 0.0156(11) 0.0013(12) O2 0.0364(11) 0.0287(13) 0.0327(13) -0.0012(10) 0.0074(9) 0.0006(10) O3 0.0375(12) 0.0407(14) 0.0259(12) 0.0017(11) 0.0029(9) 0.0024(11) O4 0.0561(15) 0.0309(14) 0.0370(14) -0.0086(11) 0.0077(11) -0.0041(11) O5 0.0445(13) 0.0338(15) 0.0613(17) 0.0001(12) 0.0144(11) 0.0013(11) O6 0.0737(17) 0.0449(17) 0.0318(14) 0.0021(12) -0.0027(12) 0.0172(13) O7 0.0647(16) 0.0448(16) 0.0337(14) -0.0052(12) 0.0172(12) -0.0025(12) N1 0.0405(14) 0.0289(16) 0.0276(15) -0.0021(12) 0.0074(11) 0.0012(12) C1 0.065(2) 0.030(2) 0.045(2) -0.0077(17) 0.0108(18) -0.0095(18) C2 0.056(2) 0.039(2) 0.056(3) -0.002(2) 0.0029(19) -0.0137(19) C3 0.0395(19) 0.032(2) 0.055(2) 0.0183(19) 0.0005(17) 0.0038(16) C4 0.048(2) 0.056(3) 0.118(4) 0.023(3) 0.019(2) -0.007(2) C5 0.0418(18) 0.037(2) 0.0227(17) -0.0039(15) 0.0022(13) 0.0055(16) C6 0.067(2) 0.047(2) 0.038(2) 0.0079(19) 0.0083(18) 0.014(2) C7 0.051(2) 0.077(3) 0.037(2) -0.009(2) 0.0114(17) 0.020(2) C8 0.070(2) 0.046(2) 0.031(2) -0.0071(18) 0.0079(17) -0.008(2) C9 0.0334(16) 0.0298(19) 0.0305(19) -0.0040(15) 0.0029(13) 0.0065(15) C10 0.0427(18) 0.0255(18) 0.0332(19) -0.0016(15) 0.0066(14) 0.0009(15) C11 0.049(2) 0.034(2) 0.045(2) 0.0043(17) 0.0030(16) 0.0069(16) C12 0.057(2) 0.039(2) 0.044(2) -0.0011(18) 0.0101(17) -0.0089(19) C13 0.0317(15) 0.0263(18) 0.0280(17) -0.0018(14) 0.0050(13) -0.0002(14) C14 0.0457(19) 0.034(2) 0.0326(19) 0.0004(16) 0.0083(15) 0.0012(16) C15 0.045(2) 0.039(2) 0.050(2) 0.0068(18) 0.0081(17) 0.0101(17) C16 0.0388(19) 0.035(2) 0.065(3) -0.0027(19) 0.0132(18) 0.0075(16) C17 0.0377(18) 0.045(2) 0.041(2) -0.0100(18) 0.0162(15) -0.0022(17) C18 0.0373(17) 0.0298(19) 0.0329(19) -0.0028(15) 0.0073(14) -0.0039(15) C19 0.0437(19) 0.037(2) 0.0258(18) -0.0026(15) 0.0059(14) -0.0055(16) C20 0.0451(19) 0.038(2) 0.0255(18) -0.0031(15) 0.0068(14) -0.0079(16) C21 0.065(2) 0.042(2) 0.030(2) 0.0014(17) -0.0031(17) -0.0003(19) C22 0.075(3) 0.037(2) 0.029(2) 0.0103(17) 0.0077(18) -0.003(2) C23 0.076(3) 0.069(3) 0.038(2) 0.006(2) 0.018(2) -0.011(2) C24 0.052(2) 0.063(3) 0.040(2) 0.004(2) 0.0170(17) -0.006(2) C25 0.054(2) 0.042(2) 0.048(2) 0.0088(19) 0.0179(18) -0.0031(19) _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 Pd C1 2.028(3) . ? Pd O1 2.136(2) . ? Pd P 2.1431(11) . ? Pd N1 2.145(3) . ? S O6 1.435(2) . ? S O7 1.437(2) . ? S O5 1.441(2) . ? S C25 1.804(4) . ? P O2 1.607(2) . ? P O3 1.614(2) . ? P C13 1.788(3) . ? F1 C25 1.337(4) . ? F2 C25 1.336(4) . ? F3 C25 1.332(4) . ? O1 C3 1.233(4) . ? O2 C10 1.466(4) . ? O3 C20 1.405(4) . ? O4 C9 1.344(4) . ? O4 C8 1.459(4) . ? N1 C9 1.276(4) . ? N1 C5 1.507(4) . ? C1 C2 1.505(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.472(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.501(5) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C7 1.511(4) . ? C5 C6 1.511(5) . ? C5 C8 1.532(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.520(5) . ? C10 C12 1.515(5) . ? C10 C11 1.536(4) . ? 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 C18 1.396(4) . ? C13 C14 1.403(4) . ? C14 C15 1.375(5) . ? C14 H14 0.9500 . ? C15 C16 1.365(5) . ? C15 H15 0.9500 . ? C16 C17 1.383(5) . ? C16 H16 0.9500 . ? C17 C18 1.405(4) . ? C17 H17 0.9500 . ? C18 C19 1.473(5) . ? C19 C24 1.392(5) . ? C19 C20 1.400(5) . ? C20 C21 1.385(5) . ? C21 C22 1.388(5) . ? C21 H21 0.9500 . ? C22 C23 1.382(5) . ? C22 H22 0.9500 . ? C23 C24 1.368(5) . ? C23 H23 0.9500 . ? C24 H24 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 C1 Pd O1 81.97(13) . . ? C1 Pd P 88.27(11) . . ? O1 Pd P 167.90(7) . . ? C1 Pd N1 175.35(12) . . ? O1 Pd N1 98.39(10) . . ? P Pd N1 91.91(8) . . ? O6 S O7 114.90(15) . . ? O6 S O5 115.14(15) . . ? O7 S O5 115.07(15) . . ? O6 S C25 102.94(18) . . ? O7 S C25 102.84(17) . . ? O5 S C25 103.45(16) . . ? O2 P O3 104.35(12) . . ? O2 P C13 101.52(12) . . ? O3 P C13 100.90(13) . . ? O2 P Pd 113.07(9) . . ? O3 P Pd 114.56(9) . . ? C13 P Pd 120.34(11) . . ? C3 O1 Pd 112.0(2) . . ? C10 O2 P 123.30(18) . . ? C20 O3 P 117.80(19) . . ? C9 O4 C8 105.5(3) . . ? C9 N1 C5 107.5(3) . . ? C9 N1 Pd 125.5(2) . . ? C5 N1 Pd 126.8(2) . . ? C2 C1 Pd 107.1(3) . . ? C2 C1 H1A 110.3 . . ? Pd C1 H1A 110.3 . . ? C2 C1 H1B 110.3 . . ? Pd C1 H1B 110.3 . . ? H1A C1 H1B 108.6 . . ? C3 C2 C1 114.1(3) . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? O1 C3 C2 119.9(3) . . ? O1 C3 C4 120.4(4) . . ? C2 C3 C4 119.5(4) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 C7 108.9(2) . . ? N1 C5 C6 110.2(3) . . ? C7 C5 C6 111.1(3) . . ? N1 C5 C8 101.9(3) . . ? C7 C5 C8 111.5(3) . . ? C6 C5 C8 112.9(3) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O4 C8 C5 105.2(3) . . ? O4 C8 H8A 110.7 . . ? C5 C8 H8A 110.7 . . ? O4 C8 H8B 110.7 . . ? C5 C8 H8B 110.7 . . ? H8A C8 H8B 108.8 . . ? N1 C9 O4 118.1(3) . . ? N1 C9 C10 126.6(3) . . ? O4 C9 C10 115.3(3) . . ? O2 C10 C12 104.3(3) . . ? O2 C10 C9 107.0(2) . . ? C12 C10 C9 112.1(3) . . ? O2 C10 C11 111.5(3) . . ? C12 C10 C11 111.3(3) . . ? C9 C10 C11 110.4(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 121.7(3) . . ? C18 C13 P 118.4(2) . . ? C14 C13 P 119.8(2) . . ? C15 C14 C13 118.7(3) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C16 C15 C14 120.6(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 121.3(3) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C16 C17 C18 120.1(3) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C13 C18 C17 117.5(3) . . ? C13 C18 C19 120.7(3) . . ? C17 C18 C19 121.8(3) . . ? C24 C19 C20 116.6(3) . . ? C24 C19 C18 122.4(3) . . ? C20 C19 C18 121.0(3) . . ? C21 C20 C19 122.7(3) . . ? C21 C20 O3 116.6(3) . . ? C19 C20 O3 120.7(3) . . ? C20 C21 C22 118.2(3) . . ? C20 C21 H21 120.9 . . ? C22 C21 H21 120.9 . . ? C23 C22 C21 120.2(3) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 120.3(4) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C19 121.8(4) . . ? C23 C24 H24 119.1 . . ? C19 C24 H24 119.1 . . ? F3 C25 F2 107.1(3) . . ? F3 C25 F1 106.5(3) . . ? F2 C25 F1 107.3(3) . . ? F3 C25 S 111.9(3) . . ? F2 C25 S 112.4(3) . . ? F1 C25 S 111.4(3) . . ? 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 C1 Pd P O2 -177.72(13) . . . . ? O1 Pd P O2 -141.6(3) . . . . ? N1 Pd P O2 6.93(11) . . . . ? C1 Pd P O3 -58.33(15) . . . . ? O1 Pd P O3 -22.2(4) . . . . ? N1 Pd P O3 126.32(12) . . . . ? C1 Pd P C13 62.23(16) . . . . ? O1 Pd P C13 98.3(3) . . . . ? N1 Pd P C13 -113.12(13) . . . . ? C1 Pd O1 C3 14.2(2) . . . . ? P Pd O1 C3 -22.3(5) . . . . ? N1 Pd O1 C3 -170.4(2) . . . . ? O3 P O2 C10 -89.0(2) . . . . ? C13 P O2 C10 166.5(2) . . . . ? Pd P O2 C10 36.1(2) . . . . ? O2 P O3 C20 -55.1(2) . . . . ? C13 P O3 C20 49.9(3) . . . . ? Pd P O3 C20 -179.2(2) . . . . ? C1 Pd N1 C9 -113.6(15) . . . . ? O1 Pd N1 C9 152.2(2) . . . . ? P Pd N1 C9 -21.4(2) . . . . ? C1 Pd N1 C5 60.6(16) . . . . ? O1 Pd N1 C5 -33.6(2) . . . . ? P Pd N1 C5 152.8(2) . . . . ? O1 Pd C1 C2 -18.9(2) . . . . ? P Pd C1 C2 153.9(2) . . . . ? N1 Pd C1 C2 -113.7(15) . . . . ? Pd C1 C2 C3 22.6(4) . . . . ? Pd O1 C3 C2 -4.6(4) . . . . ? Pd O1 C3 C4 170.6(3) . . . . ? C1 C2 C3 O1 -12.4(5) . . . . ? C1 C2 C3 C4 172.3(3) . . . . ? C9 N1 C5 C7 -109.7(3) . . . . ? Pd N1 C5 C7 75.2(3) . . . . ? C9 N1 C5 C6 128.2(3) . . . . ? Pd N1 C5 C6 -46.9(3) . . . . ? C9 N1 C5 C8 8.2(3) . . . . ? Pd N1 C5 C8 -166.9(2) . . . . ? C9 O4 C8 C5 12.8(3) . . . . ? N1 C5 C8 O4 -12.5(3) . . . . ? C7 C5 C8 O4 103.5(3) . . . . ? C6 C5 C8 O4 -130.6(3) . . . . ? C5 N1 C9 O4 -0.2(4) . . . . ? Pd N1 C9 O4 174.93(18) . . . . ? C5 N1 C9 C10 178.5(3) . . . . ? Pd N1 C9 C10 -6.3(4) . . . . ? C8 O4 C9 N1 -8.4(4) . . . . ? C8 O4 C9 C10 172.7(3) . . . . ? P O2 C10 C12 172.7(2) . . . . ? P O2 C10 C9 -68.3(3) . . . . ? P O2 C10 C11 52.6(3) . . . . ? N1 C9 C10 O2 51.8(4) . . . . ? O4 C9 C10 O2 -129.5(3) . . . . ? N1 C9 C10 C12 165.5(3) . . . . ? O4 C9 C10 C12 -15.7(4) . . . . ? N1 C9 C10 C11 -69.8(4) . . . . ? O4 C9 C10 C11 108.9(3) . . . . ? O2 P C13 C18 76.9(3) . . . . ? O3 P C13 C18 -30.4(3) . . . . ? Pd P C13 C18 -157.5(2) . . . . ? O2 P C13 C14 -105.2(3) . . . . ? O3 P C13 C14 147.5(2) . . . . ? Pd P C13 C14 20.4(3) . . . . ? C18 C13 C14 C15 -1.5(5) . . . . ? P C13 C14 C15 -179.3(3) . . . . ? C13 C14 C15 C16 2.5(5) . . . . ? C14 C15 C16 C17 -2.1(6) . . . . ? C15 C16 C17 C18 0.7(5) . . . . ? C14 C13 C18 C17 0.2(5) . . . . ? P C13 C18 C17 178.1(2) . . . . ? C14 C13 C18 C19 -178.5(3) . . . . ? P C13 C18 C19 -0.7(4) . . . . ? C16 C17 C18 C13 0.2(5) . . . . ? C16 C17 C18 C19 178.9(3) . . . . ? C13 C18 C19 C24 -158.6(3) . . . . ? C17 C18 C19 C24 22.7(5) . . . . ? C13 C18 C19 C20 20.1(5) . . . . ? C17 C18 C19 C20 -158.6(3) . . . . ? C24 C19 C20 C21 -3.1(5) . . . . ? C18 C19 C20 C21 178.2(3) . . . . ? C24 C19 C20 O3 178.4(3) . . . . ? C18 C19 C20 O3 -0.3(5) . . . . ? P O3 C20 C21 141.9(3) . . . . ? P O3 C20 C19 -39.6(4) . . . . ? C19 C20 C21 C22 1.9(5) . . . . ? O3 C20 C21 C22 -179.6(3) . . . . ? C20 C21 C22 C23 1.8(6) . . . . ? C21 C22 C23 C24 -4.0(6) . . . . ? C22 C23 C24 C19 2.7(6) . . . . ? C20 C19 C24 C23 0.8(5) . . . . ? C18 C19 C24 C23 179.5(4) . . . . ? O6 S C25 F3 59.5(3) . . . . ? O7 S C25 F3 179.2(2) . . . . ? O5 S C25 F3 -60.7(3) . . . . ? O6 S C25 F2 -61.0(3) . . . . ? O7 S C25 F2 58.7(3) . . . . ? O5 S C25 F2 178.8(2) . . . . ? O6 S C25 F1 178.6(3) . . . . ? O7 S C25 F1 -61.7(3) . . . . ? O5 S C25 F1 58.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.757 _refine_diff_density_min -1.099 _refine_diff_density_rms 0.148 data_welt22 _database_code_depnum_ccdc_archive 'CCDC 627980' _audit_creation_date 22-1-05 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 Cl2 N O2 P Pd, C H2 Cl2' _chemical_formula_sum 'C19 H22 Cl4 N O2 P Pd' _chemical_formula_weight 575.55 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' 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 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 29.65600(10) _cell_length_b 8.96500(10) _cell_length_c 8.6870(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2309.58(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3759 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.351 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 6464 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 30.03 _reflns_number_total 6464 _reflns_number_gt 5941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0380P)^2^+1.5354P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.49(3) _refine_ls_number_reflns 6465 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 Pd Pd 0.329962(6) 0.37817(2) 0.59632(4) 0.01841(6) Uani 1 1 d . . . Cl1 Cl 0.29804(3) 0.24622(10) 0.38574(10) 0.03251(18) Uani 1 1 d . . . Cl2 Cl 0.38269(3) 0.47853(11) 0.43336(10) 0.03079(19) Uani 1 1 d . . . Cl3 Cl 0.41647(5) 0.03806(19) 1.0824(2) 0.0836(5) Uani 1 1 d . . . Cl4 Cl 0.46908(5) 0.12630(19) 1.34878(19) 0.0722(4) Uani 1 1 d . . . P P 0.37024(3) 0.49168(9) 0.77469(10) 0.02070(16) Uani 1 1 d . . . O1 O 0.24838(8) 0.3045(3) 0.9879(3) 0.0277(5) Uani 1 1 d . . . O2 O 0.34761(8) 0.4791(3) 0.9444(3) 0.0259(5) Uani 1 1 d . . . N N 0.28032(8) 0.3244(3) 0.7543(3) 0.0207(5) Uani 1 1 d . . . C1 C 0.22127(13) 0.1479(4) 0.6647(5) 0.0337(8) Uani 1 1 d . . . H1A H 0.2402 0.1271 0.5749 0.051 Uiso 1 1 calc . . . H1B H 0.1894 0.1383 0.6361 0.051 Uiso 1 1 calc . . . H1C H 0.2283 0.0767 0.7469 0.051 Uiso 1 1 calc . . . C2 C 0.21423(12) 0.4255(4) 0.6106(5) 0.0338(7) Uani 1 1 d . . . H2A H 0.2218 0.5239 0.6520 0.051 Uiso 1 1 calc . . . H2B H 0.1815 0.4178 0.5977 0.051 Uiso 1 1 calc . . . H2C H 0.2290 0.4121 0.5106 0.051 Uiso 1 1 calc . . . C3 C 0.23030(11) 0.3055(4) 0.7211(4) 0.0251(6) Uani 1 1 d . . . C4 C 0.21029(11) 0.3270(4) 0.8833(4) 0.0292(7) Uani 1 1 d . . . H4A H 0.1976 0.4286 0.8950 0.035 Uiso 1 1 calc . . . H4B H 0.1862 0.2531 0.9034 0.035 Uiso 1 1 calc . . . C5 C 0.28527(10) 0.3185(3) 0.9004(4) 0.0220(6) Uani 1 1 d . . . C6 C 0.32879(11) 0.3355(4) 0.9858(4) 0.0261(7) Uani 1 1 d . . . H6A H 0.3234 0.3307 1.0982 0.031 Uiso 1 1 calc . . . H6B H 0.3499 0.2546 0.9572 0.031 Uiso 1 1 calc . . . C7 C 0.42630(10) 0.4206(4) 0.8079(4) 0.0266(7) Uani 1 1 d . . . C8 C 0.44747(12) 0.3205(4) 0.7094(5) 0.0295(7) Uani 1 1 d . . . H8 H 0.4325 0.2877 0.6188 0.035 Uiso 1 1 calc . . . C9 C 0.49067(13) 0.2678(4) 0.7430(6) 0.0405(9) Uani 1 1 d . . . H9 H 0.5052 0.2003 0.6747 0.049 Uiso 1 1 calc . . . C10 C 0.51213(14) 0.3131(5) 0.8740(8) 0.0574(14) Uani 1 1 d . . . H10 H 0.5415 0.2770 0.8962 0.069 Uiso 1 1 calc . . . C11 C 0.49160(18) 0.4103(6) 0.9740(8) 0.0686(19) Uani 1 1 d . . . H11 H 0.5070 0.4411 1.0645 0.082 Uiso 1 1 calc . . . C12 C 0.44807(14) 0.4648(5) 0.9436(6) 0.0494(12) Uani 1 1 d . . . H12 H 0.4336 0.5306 1.0139 0.059 Uiso 1 1 calc . . . C13 C 0.37317(11) 0.6914(4) 0.7547(4) 0.0240(6) Uani 1 1 d . . . C14 C 0.41340(13) 0.7651(4) 0.7281(6) 0.0376(9) Uani 1 1 d . . . H14 H 0.4410 0.7114 0.7292 0.045 Uiso 1 1 calc . . . C15 C 0.41335(14) 0.9184(4) 0.6996(7) 0.0473(11) Uani 1 1 d . . . H15 H 0.4410 0.9689 0.6808 0.057 Uiso 1 1 calc . . . C16 C 0.37386(15) 0.9956(4) 0.6989(5) 0.0386(9) Uani 1 1 d . . . H16 H 0.3741 1.0999 0.6797 0.046 Uiso 1 1 calc . . . C17 C 0.33317(12) 0.9231(4) 0.7260(5) 0.0315(8) Uani 1 1 d . . . H17 H 0.3057 0.9777 0.7254 0.038 Uiso 1 1 calc . . . C18 C 0.33280(10) 0.7696(4) 0.7541(4) 0.0270(7) Uani 1 1 d . . . H18 H 0.3051 0.7192 0.7726 0.032 Uiso 1 1 calc . . . C19 C 0.4172(2) 0.1306(9) 1.2565(9) 0.091(3) Uani 1 1 d . . . H19A H 0.3943 0.0854 1.3250 0.109 Uiso 1 1 calc . . . H19B H 0.4086 0.2359 1.2391 0.109 Uiso 1 1 calc . . . 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 Pd 0.02076(10) 0.01802(10) 0.01646(10) -0.00108(11) -0.00004(10) -0.00026(7) Cl1 0.0410(4) 0.0356(4) 0.0209(3) -0.0072(3) -0.0006(3) -0.0078(4) Cl2 0.0305(4) 0.0349(5) 0.0270(4) 0.0028(3) 0.0076(3) -0.0027(3) Cl3 0.0672(8) 0.0983(11) 0.0854(11) -0.0388(10) -0.0241(9) 0.0272(8) Cl4 0.0549(8) 0.0975(12) 0.0640(9) -0.0272(7) -0.0074(7) 0.0140(7) P 0.0197(3) 0.0201(4) 0.0223(4) -0.0026(3) -0.0019(3) -0.0006(3) O1 0.0269(11) 0.0339(13) 0.0224(11) 0.0018(10) 0.0055(9) -0.0018(10) O2 0.0271(11) 0.0268(12) 0.0238(11) -0.0030(9) -0.0008(9) -0.0036(9) N 0.0208(12) 0.0193(12) 0.0219(13) -0.0017(10) -0.0005(10) -0.0034(9) C1 0.0315(18) 0.0288(17) 0.041(2) -0.0078(15) 0.0013(15) -0.0104(14) C2 0.0329(16) 0.0376(16) 0.0308(19) 0.0003(18) -0.0039(16) 0.0079(13) C3 0.0220(14) 0.0262(16) 0.0271(16) -0.0053(13) -0.0013(12) -0.0005(12) C4 0.0226(15) 0.0353(18) 0.0298(17) -0.0016(15) 0.0025(13) -0.0009(13) C5 0.0263(15) 0.0179(14) 0.0218(16) 0.0005(12) 0.0017(11) -0.0007(11) C6 0.0305(17) 0.0273(17) 0.0206(16) 0.0042(14) -0.0026(12) -0.0002(12) C7 0.0188(14) 0.0227(15) 0.0384(19) 0.0003(14) -0.0049(12) -0.0002(11) C8 0.0252(16) 0.0283(17) 0.0351(19) 0.0031(14) 0.0002(13) 0.0014(13) C9 0.0288(18) 0.0317(19) 0.061(3) 0.0047(18) 0.0009(17) 0.0071(14) C10 0.030(2) 0.038(2) 0.104(4) -0.005(3) -0.028(2) 0.0083(17) C11 0.053(3) 0.048(3) 0.104(5) -0.029(3) -0.053(3) 0.015(2) C12 0.042(2) 0.040(2) 0.067(3) -0.022(2) -0.027(2) 0.0121(17) C13 0.0261(15) 0.0204(14) 0.0255(16) -0.0025(12) -0.0003(12) 0.0009(11) C14 0.0264(16) 0.0232(17) 0.063(3) -0.0011(17) 0.0060(16) 0.0011(13) C15 0.0337(19) 0.0245(18) 0.084(3) 0.004(2) 0.008(2) -0.0060(15) C16 0.050(2) 0.0210(17) 0.044(2) 0.0006(15) 0.0001(18) 0.0015(15) C17 0.0335(18) 0.0259(17) 0.035(2) -0.0013(16) -0.0034(14) 0.0099(13) C18 0.0248(15) 0.0258(17) 0.0305(19) -0.0001(14) -0.0009(12) 0.0015(11) C19 0.050(3) 0.144(7) 0.080(5) -0.053(4) -0.011(3) 0.026(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 Pd N 2.069(3) . ? Pd P 2.2052(9) . ? Pd Cl2 2.2932(9) . ? Pd Cl1 2.3754(9) . ? Cl3 C19 1.724(7) . ? Cl4 C19 1.734(7) . ? P O2 1.624(3) . ? P C13 1.801(3) . ? P C7 1.804(3) . ? O1 C5 1.338(4) . ? O1 C4 1.464(4) . ? O2 C6 1.448(4) . ? N C5 1.279(4) . ? N C3 1.520(4) . ? C1 C3 1.519(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.519(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.541(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.496(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.390(5) . ? C7 C12 1.402(6) . ? C8 C9 1.396(5) . ? C8 H8 0.9500 . ? C9 C10 1.366(7) . ? C9 H9 0.9500 . ? C10 C11 1.373(8) . ? C10 H10 0.9500 . ? C11 C12 1.405(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.383(5) . ? C13 C18 1.387(4) . ? C14 C15 1.397(5) . ? C14 H14 0.9500 . ? C15 C16 1.361(6) . ? C15 H15 0.9500 . ? C16 C17 1.390(6) . ? C16 H16 0.9500 . ? C17 C18 1.398(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? 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 N Pd P 91.54(8) . . ? N Pd Cl2 170.34(8) . . ? P Pd Cl2 83.30(3) . . ? N Pd Cl1 96.38(7) . . ? P Pd Cl1 170.69(3) . . ? Cl2 Pd Cl1 89.53(3) . . ? O2 P C13 100.16(14) . . ? O2 P C7 102.21(16) . . ? C13 P C7 108.79(15) . . ? O2 P Pd 112.47(9) . . ? C13 P Pd 114.65(11) . . ? C7 P Pd 116.65(12) . . ? C5 O1 C4 105.4(2) . . ? C6 O2 P 116.5(2) . . ? C5 N C3 107.2(3) . . ? C5 N Pd 125.9(2) . . ? C3 N Pd 126.5(2) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 C2 113.5(3) . . ? C1 C3 N 109.7(3) . . ? C2 C3 N 110.3(3) . . ? C1 C3 C4 110.1(3) . . ? C2 C3 C4 111.6(3) . . ? N C3 C4 100.9(3) . . ? O1 C4 C3 104.6(3) . . ? O1 C4 H4A 110.8 . . ? C3 C4 H4A 110.8 . . ? O1 C4 H4B 110.8 . . ? C3 C4 H4B 110.8 . . ? H4A C4 H4B 108.9 . . ? N C5 O1 118.3(3) . . ? N C5 C6 125.9(3) . . ? O1 C5 C6 115.7(3) . . ? O2 C6 C5 107.4(3) . . ? O2 C6 H6A 110.2 . . ? C5 C6 H6A 110.2 . . ? O2 C6 H6B 110.2 . . ? C5 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? C8 C7 C12 119.5(3) . . ? C8 C7 P 123.1(3) . . ? C12 C7 P 117.3(3) . . ? C7 C8 C9 120.3(4) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.1(4) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.6(4) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 120.6(4) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C7 C12 C11 118.9(4) . . ? C7 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C14 C13 C18 120.2(3) . . ? C14 C13 P 122.2(3) . . ? C18 C13 P 117.4(2) . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 120.2(4) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.5(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C13 C18 C17 119.4(3) . . ? C13 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? Cl3 C19 Cl4 114.0(3) . . ? Cl3 C19 H19A 108.8 . . ? Cl4 C19 H19A 108.8 . . ? Cl3 C19 H19B 108.8 . . ? Cl4 C19 H19B 108.8 . . ? H19A C19 H19B 107.6 . . ? 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 N Pd P O2 3.04(12) . . . . ? Cl2 Pd P O2 174.84(10) . . . . ? Cl1 Pd P O2 -145.3(2) . . . . ? N Pd P C13 -110.53(14) . . . . ? Cl2 Pd P C13 61.27(12) . . . . ? Cl1 Pd P C13 101.1(2) . . . . ? N Pd P C7 120.65(15) . . . . ? Cl2 Pd P C7 -67.55(13) . . . . ? Cl1 Pd P C7 -27.7(3) . . . . ? C13 P O2 C6 164.2(2) . . . . ? C7 P O2 C6 -83.9(2) . . . . ? Pd P O2 C6 42.0(2) . . . . ? P Pd N C5 -21.0(3) . . . . ? Cl2 Pd N C5 -78.5(6) . . . . ? Cl1 Pd N C5 154.1(3) . . . . ? P Pd N C3 150.1(2) . . . . ? Cl2 Pd N C3 92.6(5) . . . . ? Cl1 Pd N C3 -34.8(2) . . . . ? C5 N C3 C1 -103.0(3) . . . . ? Pd N C3 C1 84.5(3) . . . . ? C5 N C3 C2 131.2(3) . . . . ? Pd N C3 C2 -41.2(4) . . . . ? C5 N C3 C4 13.1(3) . . . . ? Pd N C3 C4 -159.3(2) . . . . ? C5 O1 C4 C3 17.5(3) . . . . ? C1 C3 C4 O1 97.7(3) . . . . ? C2 C3 C4 O1 -135.3(3) . . . . ? N C3 C4 O1 -18.2(3) . . . . ? C3 N C5 O1 -2.6(4) . . . . ? Pd N C5 O1 169.9(2) . . . . ? C3 N C5 C6 -178.5(3) . . . . ? Pd N C5 C6 -6.0(5) . . . . ? C4 O1 C5 N -10.0(4) . . . . ? C4 O1 C5 C6 166.3(3) . . . . ? P O2 C6 C5 -75.0(3) . . . . ? N C5 C6 O2 57.5(4) . . . . ? O1 C5 C6 O2 -118.5(3) . . . . ? O2 P C7 C8 135.6(3) . . . . ? C13 P C7 C8 -119.0(3) . . . . ? Pd P C7 C8 12.5(4) . . . . ? O2 P C7 C12 -41.4(4) . . . . ? C13 P C7 C12 63.9(4) . . . . ? Pd P C7 C12 -164.5(3) . . . . ? C12 C7 C8 C9 -1.9(6) . . . . ? P C7 C8 C9 -178.9(3) . . . . ? C7 C8 C9 C10 0.8(6) . . . . ? C8 C9 C10 C11 0.1(8) . . . . ? C9 C10 C11 C12 0.2(10) . . . . ? C8 C7 C12 C11 2.1(7) . . . . ? P C7 C12 C11 179.3(5) . . . . ? C10 C11 C12 C7 -1.3(9) . . . . ? O2 P C13 C14 122.5(3) . . . . ? C7 P C13 C14 15.7(4) . . . . ? Pd P C13 C14 -116.9(3) . . . . ? O2 P C13 C18 -62.8(3) . . . . ? C7 P C13 C18 -169.5(3) . . . . ? Pd P C13 C18 57.9(3) . . . . ? C18 C13 C14 C15 -0.4(7) . . . . ? P C13 C14 C15 174.2(4) . . . . ? C13 C14 C15 C16 0.4(8) . . . . ? C14 C15 C16 C17 -0.2(8) . . . . ? C15 C16 C17 C18 -0.1(7) . . . . ? C14 C13 C18 C17 0.2(6) . . . . ? P C13 C18 C17 -174.7(3) . . . . ? C16 C17 C18 C13 0.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.308 _refine_diff_density_min -0.849 _refine_diff_density_rms 0.116 data_compound_5a _database_code_depnum_ccdc_archive 'CCDC 627981' _audit_creation_date 22-1-05 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H23 F3 N O5 P Pd S' _chemical_formula_sum 'C20 H23 F3 N O5 P Pd S' _chemical_formula_weight 583.82 _chemical_absolute_configuration . 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' N N 0.0061 0.0033 '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' Pd Pd -0.9988 1.0072 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 11.5800(2) _cell_length_b 9.1090(2) _cell_length_c 22.6660(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.6710(9) _cell_angle_gamma 90.00 _cell_volume 2390.70(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 40704 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.984 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean . _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 6971 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 30.01 _reflns_number_total 6970 _reflns_number_gt 4006 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0000P)^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 6970 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.898 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd Pd 0.301781(17) 0.30939(2) 0.387188(9) 0.04044(8) Uani 1 1 d . . . S1 S 0.50216(7) 0.21176(10) 0.29055(4) 0.0556(2) Uani 1 1 d . . . P P 0.21413(6) 0.44092(8) 0.45189(3) 0.04073(17) Uani 1 1 d . . . F1 F 0.7075(2) 0.0996(4) 0.28456(12) 0.1364(12) Uani 1 1 d . . . F2 F 0.6446(3) 0.1189(5) 0.37139(11) 0.1593(15) Uani 1 1 d . . . F3 F 0.5802(3) -0.0457(4) 0.31500(16) 0.1473(12) Uani 1 1 d . . . O1 O -0.04239(18) 0.2923(3) 0.31650(10) 0.0664(7) Uani 1 1 d . . . O2 O 0.07681(16) 0.4471(2) 0.43831(8) 0.0492(5) Uani 1 1 d . . . O4 O 0.40838(17) 0.1767(2) 0.32999(9) 0.0573(6) Uani 1 1 d . . . O3 O 0.5457(3) 0.3562(3) 0.29749(13) 0.0993(9) Uani 1 1 d . . . O5 O 0.4839(2) 0.1632(4) 0.23187(10) 0.0901(9) Uani 1 1 d . . . N N 0.1478(2) 0.2692(3) 0.33449(10) 0.0443(6) Uani 1 1 d . . . C1 C 0.1806(4) 0.1474(6) 0.23882(17) 0.0979(16) Uani 1 1 d . . . H1A H 0.1654 0.2427 0.2203 0.147 Uiso 1 1 calc . . . H1B H 0.1534 0.0687 0.2126 0.147 Uiso 1 1 calc . . . H1C H 0.2637 0.1363 0.2460 0.147 Uiso 1 1 calc . . . C2 C 0.1470(4) 0.0013(4) 0.3304(2) 0.0929(14) Uani 1 1 d . . . H2A H 0.2270 0.0067 0.3448 0.139 Uiso 1 1 calc . . . H2B H 0.1378 -0.0841 0.3045 0.139 Uiso 1 1 calc . . . H2C H 0.0950 -0.0080 0.3641 0.139 Uiso 1 1 calc . . . C3 C 0.1178(3) 0.1388(4) 0.29655(13) 0.0516(8) Uani 1 1 d . . . C4 C -0.0110(3) 0.1560(5) 0.28692(18) 0.0770(11) Uani 1 1 d . . . H4A H -0.0298 0.1616 0.2443 0.092 Uiso 1 1 calc . . . H4B H -0.0531 0.0719 0.3041 0.092 Uiso 1 1 calc . . . C5 C 0.0554(3) 0.3416(4) 0.34158(13) 0.0506(8) Uani 1 1 d . . . C6 C 0.0424(3) 0.4773(4) 0.37825(14) 0.0577(8) Uani 1 1 d . . . H6A H 0.0910 0.5569 0.3621 0.069 Uiso 1 1 calc . . . H6B H -0.0390 0.5104 0.3770 0.069 Uiso 1 1 calc . . . C7 C 0.4423(3) 0.3349(4) 0.44086(15) 0.0663(10) Uani 1 1 d . . . H7A H 0.4206 0.3915 0.4758 0.099 Uiso 1 1 calc . . . H7B H 0.5028 0.3873 0.4196 0.099 Uiso 1 1 calc . . . H7C H 0.4711 0.2383 0.4531 0.099 Uiso 1 1 calc . . . C8 C 0.2101(2) 0.3728(3) 0.52713(12) 0.0438(7) Uani 1 1 d . . . C9 C 0.2753(3) 0.4348(4) 0.57144(14) 0.0620(9) Uani 1 1 d . . . H9 H 0.3224 0.5176 0.5634 0.074 Uiso 1 1 calc . . . C10 C 0.2728(3) 0.3764(5) 0.62841(15) 0.0760(11) Uani 1 1 d . . . H10 H 0.3187 0.4188 0.6590 0.091 Uiso 1 1 calc . . . C11 C 0.2046(4) 0.2590(5) 0.63989(17) 0.0760(12) Uani 1 1 d . . . H11 H 0.2024 0.2198 0.6787 0.091 Uiso 1 1 calc . . . C12 C 0.1392(4) 0.1969(4) 0.59626(19) 0.0783(12) Uani 1 1 d . . . H12 H 0.0913 0.1152 0.6049 0.094 Uiso 1 1 calc . . . C13 C 0.1421(3) 0.2523(4) 0.53929(15) 0.0629(9) Uani 1 1 d . . . H13 H 0.0975 0.2075 0.5088 0.075 Uiso 1 1 calc . . . C14 C 0.2554(3) 0.6308(3) 0.45793(13) 0.0534(8) Uani 1 1 d . . . C15 C 0.3462(4) 0.6884(4) 0.42734(16) 0.0740(11) Uani 1 1 d . . . H15 H 0.3908 0.6287 0.4019 0.089 Uiso 1 1 calc . . . C16 C 0.3718(5) 0.8401(6) 0.4349(2) 0.1054(17) Uani 1 1 d . . . H16 H 0.4345 0.8828 0.4143 0.126 Uiso 1 1 calc . . . C17 C 0.3071(6) 0.9240(5) 0.4712(3) 0.115(2) Uani 1 1 d . . . H17 H 0.3252 1.0251 0.4758 0.138 Uiso 1 1 calc . . . C18 C 0.2192(6) 0.8676(5) 0.5005(2) 0.1149(19) Uani 1 1 d . . . H18 H 0.1753 0.9284 0.5259 0.138 Uiso 1 1 calc . . . C19 C 0.1909(4) 0.7214(4) 0.49433(18) 0.0795(12) Uani 1 1 d . . . H19 H 0.1270 0.6823 0.5151 0.095 Uiso 1 1 calc . . . C20 C 0.6164(4) 0.0943(6) 0.31744(19) 0.0828(12) Uani 1 1 d . . . 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 Pd 0.03304(12) 0.04599(14) 0.04227(13) -0.00797(10) -0.00065(8) -0.00128(10) S1 0.0431(4) 0.0716(6) 0.0521(5) 0.0020(4) 0.0016(3) 0.0110(4) P 0.0425(4) 0.0397(4) 0.0400(4) -0.0032(3) 0.0007(3) 0.0012(3) F1 0.0584(14) 0.228(4) 0.124(2) 0.024(2) 0.0272(14) 0.0572(19) F2 0.121(2) 0.276(4) 0.0799(18) -0.008(2) -0.0354(16) 0.100(3) F3 0.149(3) 0.107(2) 0.187(3) 0.021(2) 0.017(2) 0.060(2) O1 0.0412(12) 0.0859(18) 0.0719(15) -0.0154(13) -0.0142(11) 0.0062(12) O2 0.0409(10) 0.0604(13) 0.0462(11) -0.0042(10) 0.0001(9) 0.0105(10) O4 0.0431(12) 0.0687(15) 0.0603(13) -0.0169(11) 0.0087(10) 0.0018(11) O3 0.104(2) 0.074(2) 0.120(2) 0.0098(17) 0.0129(18) -0.0213(18) O5 0.0699(17) 0.152(3) 0.0481(14) -0.0134(16) 0.0012(12) 0.0264(18) N 0.0369(13) 0.0495(15) 0.0464(14) -0.0089(11) -0.0051(10) -0.0017(11) C1 0.076(3) 0.155(4) 0.063(2) -0.044(3) 0.005(2) -0.036(3) C2 0.098(3) 0.053(2) 0.126(4) -0.005(2) -0.040(3) -0.009(2) C3 0.0431(17) 0.058(2) 0.0536(18) -0.0104(15) -0.0093(14) -0.0085(15) C4 0.053(2) 0.084(3) 0.093(3) -0.024(2) -0.0160(19) -0.007(2) C5 0.0413(17) 0.065(2) 0.0455(17) -0.0008(15) -0.0083(13) 0.0013(15) C6 0.0542(19) 0.061(2) 0.0572(19) -0.0063(17) -0.0118(15) 0.0194(16) C7 0.0395(17) 0.095(3) 0.064(2) -0.025(2) -0.0075(15) 0.0017(18) C8 0.0427(16) 0.0452(17) 0.0435(16) -0.0009(13) 0.0035(13) 0.0087(14) C9 0.0535(19) 0.080(2) 0.0521(19) 0.0065(18) -0.0037(15) -0.0012(18) C10 0.076(3) 0.105(3) 0.047(2) 0.004(2) -0.0082(17) 0.019(2) C11 0.094(3) 0.081(3) 0.053(2) 0.018(2) 0.017(2) 0.039(3) C12 0.105(3) 0.049(2) 0.081(3) 0.014(2) 0.031(3) 0.006(2) C13 0.086(3) 0.0451(18) 0.058(2) 0.0001(17) 0.0096(18) -0.0026(19) C14 0.073(2) 0.0413(17) 0.0453(17) 0.0017(14) -0.0110(15) -0.0045(16) C15 0.098(3) 0.066(2) 0.058(2) 0.0142(18) -0.009(2) -0.023(2) C16 0.135(5) 0.094(4) 0.087(3) 0.039(3) -0.024(3) -0.050(3) C17 0.188(6) 0.047(3) 0.109(4) 0.007(3) -0.050(4) -0.025(3) C18 0.196(6) 0.046(3) 0.103(4) -0.015(3) -0.027(4) 0.007(3) C19 0.113(3) 0.046(2) 0.080(3) -0.0074(19) -0.001(2) 0.005(2) C20 0.064(3) 0.105(4) 0.079(3) 0.007(3) 0.001(2) 0.025(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 Pd C7 2.033(3) . y Pd P 2.1567(7) . y Pd N 2.166(2) . y Pd O4 2.1689(19) . y S1 O5 1.415(3) . ? S1 O3 1.417(3) . ? S1 O4 1.450(2) . ? S1 C20 1.802(4) . ? P O2 1.617(2) . y P C14 1.800(3) . ? P C8 1.816(3) . ? F1 C20 1.300(4) . ? F2 C20 1.282(5) . ? F3 C20 1.344(5) . ? O1 C5 1.338(4) . ? O1 C4 1.459(4) . ? O2 C6 1.441(3) . y N C5 1.269(4) . y N C3 1.505(4) . ? C1 C3 1.506(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.505(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.514(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.499(4) . y C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.371(4) . ? C8 C13 1.381(4) . ? C9 C10 1.397(5) . ? C9 H9 0.9500 . ? C10 C11 1.356(6) . ? C10 H10 0.9500 . ? C11 C12 1.361(6) . ? C11 H11 0.9500 . ? C12 C13 1.387(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.371(5) . ? C14 C19 1.391(5) . ? C15 C16 1.423(6) . ? C15 H15 0.9500 . ? C16 C17 1.356(7) . ? C16 H16 0.9500 . ? C17 C18 1.326(7) . ? C17 H17 0.9500 . ? C18 C19 1.378(6) . ? C18 H18 0.9500 . ? C19 H19 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 C7 Pd P 84.79(9) . . y C7 Pd N 175.65(13) . . y P Pd N 94.48(6) . . y C7 Pd O4 87.97(11) . . y P Pd O4 172.68(6) . . y N Pd O4 92.67(8) . . y O5 S1 O3 116.31(19) . . ? O5 S1 O4 113.94(15) . . ? O3 S1 O4 113.85(16) . . ? O5 S1 C20 103.5(2) . . ? O3 S1 C20 104.8(2) . . ? O4 S1 C20 102.29(18) . . ? O2 P C14 103.92(14) . . ? O2 P C8 98.89(12) . . ? C14 P C8 105.47(14) . . ? O2 P Pd 111.07(8) . . ? C14 P Pd 117.33(11) . . ? C8 P Pd 117.81(9) . . ? C5 O1 C4 105.5(2) . . ? C6 O2 P 116.56(18) . . ? S1 O4 Pd 132.93(14) . . ? C5 N C3 107.1(2) . . ? C5 N Pd 122.2(2) . . ? C3 N Pd 129.17(19) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N C3 C2 108.4(2) . . ? N C3 C1 110.2(3) . . ? C2 C3 C1 112.3(4) . . ? N C3 C4 102.8(3) . . ? C2 C3 C4 112.0(3) . . ? C1 C3 C4 110.7(3) . . ? O1 C4 C3 105.8(3) . . ? O1 C4 H4A 110.6 . . ? C3 C4 H4A 110.6 . . ? O1 C4 H4B 110.6 . . ? C3 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? N C5 O1 118.8(3) . . ? N C5 C6 126.1(3) . . ? O1 C5 C6 115.0(3) . . ? O2 C6 C5 109.7(2) . . ? O2 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? O2 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? Pd C7 H7A 109.5 . . ? Pd C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Pd C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 119.4(3) . . ? C9 C8 P 121.8(2) . . ? C13 C8 P 118.7(2) . . ? C8 C9 C10 120.2(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 119.7(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 120.4(4) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C8 C13 C12 119.6(4) . . ? C8 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C19 119.6(3) . . ? C15 C14 P 122.3(3) . . ? C19 C14 P 118.1(3) . . ? C14 C15 C16 118.1(4) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C17 C16 C15 120.3(5) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 121.3(5) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 120.5(5) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 120.3(4) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? F2 C20 F1 110.0(4) . . ? F2 C20 F3 106.3(4) . . ? F1 C20 F3 105.5(4) . . ? F2 C20 S1 113.4(3) . . ? F1 C20 S1 112.4(3) . . ? F3 C20 S1 108.8(3) . . ? 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 C7 Pd P O2 -172.17(15) . . . . ? N Pd P O2 3.53(11) . . . . ? O4 Pd P O2 -164.2(5) . . . . ? C7 Pd P C14 68.54(16) . . . . ? N Pd P C14 -115.76(13) . . . . ? O4 Pd P C14 76.5(5) . . . . ? C7 Pd P C8 -59.19(16) . . . . ? N Pd P C8 116.51(13) . . . . ? O4 Pd P C8 -51.3(5) . . . . ? C14 P O2 C6 80.1(2) . . . . ? C8 P O2 C6 -171.4(2) . . . . ? Pd P O2 C6 -46.9(2) . . . . ? O5 S1 O4 Pd -124.6(2) . . . . ? O3 S1 O4 Pd 12.0(3) . . . . ? C20 S1 O4 Pd 124.4(2) . . . . ? C7 Pd O4 S1 -71.5(2) . . . . ? P Pd O4 S1 -79.4(6) . . . . ? N Pd O4 S1 112.78(19) . . . . ? C7 Pd N C5 93.5(15) . . . . ? P Pd N C5 13.5(2) . . . . ? O4 Pd N C5 -168.1(2) . . . . ? C7 Pd N C3 -70.1(15) . . . . ? P Pd N C3 -150.2(2) . . . . ? O4 Pd N C3 28.3(2) . . . . ? C5 N C3 C2 -120.4(3) . . . . ? Pd N C3 C2 45.1(4) . . . . ? C5 N C3 C1 116.3(3) . . . . ? Pd N C3 C1 -78.1(3) . . . . ? C5 N C3 C4 -1.7(3) . . . . ? Pd N C3 C4 163.9(2) . . . . ? C5 O1 C4 C3 -2.3(4) . . . . ? N C3 C4 O1 2.4(4) . . . . ? C2 C3 C4 O1 118.6(3) . . . . ? C1 C3 C4 O1 -115.2(4) . . . . ? C3 N C5 O1 0.3(4) . . . . ? Pd N C5 O1 -166.5(2) . . . . ? C3 N C5 C6 177.5(3) . . . . ? Pd N C5 C6 10.7(4) . . . . ? C4 O1 C5 N 1.3(4) . . . . ? C4 O1 C5 C6 -176.2(3) . . . . ? P O2 C6 C5 77.7(3) . . . . ? N C5 C6 O2 -58.0(4) . . . . ? O1 C5 C6 O2 119.3(3) . . . . ? O2 P C8 C9 -133.3(3) . . . . ? C14 P C8 C9 -26.1(3) . . . . ? Pd P C8 C9 107.1(3) . . . . ? O2 P C8 C13 48.9(3) . . . . ? C14 P C8 C13 156.1(3) . . . . ? Pd P C8 C13 -70.7(3) . . . . ? C13 C8 C9 C10 -0.1(5) . . . . ? P C8 C9 C10 -177.9(3) . . . . ? C8 C9 C10 C11 -0.7(6) . . . . ? C9 C10 C11 C12 0.5(6) . . . . ? C10 C11 C12 C13 0.5(6) . . . . ? C9 C8 C13 C12 1.0(5) . . . . ? P C8 C13 C12 178.9(3) . . . . ? C11 C12 C13 C8 -1.2(6) . . . . ? O2 P C14 C15 -129.4(3) . . . . ? C8 P C14 C15 127.1(3) . . . . ? Pd P C14 C15 -6.3(3) . . . . ? O2 P C14 C19 49.6(3) . . . . ? C8 P C14 C19 -53.9(3) . . . . ? Pd P C14 C19 172.6(2) . . . . ? C19 C14 C15 C16 0.8(6) . . . . ? P C14 C15 C16 179.7(3) . . . . ? C14 C15 C16 C17 -0.2(7) . . . . ? C15 C16 C17 C18 0.0(9) . . . . ? C16 C17 C18 C19 -0.3(9) . . . . ? C17 C18 C19 C14 0.9(8) . . . . ? C15 C14 C19 C18 -1.1(6) . . . . ? P C14 C19 C18 179.9(4) . . . . ? O5 S1 C20 F2 -178.5(4) . . . . ? O3 S1 C20 F2 59.1(4) . . . . ? O4 S1 C20 F2 -59.9(4) . . . . ? O5 S1 C20 F1 55.9(4) . . . . ? O3 S1 C20 F1 -66.4(4) . . . . ? O4 S1 C20 F1 174.6(4) . . . . ? O5 S1 C20 F3 -60.5(3) . . . . ? O3 S1 C20 F3 177.2(3) . . . . ? O4 S1 C20 F3 58.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.517 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.087 data_compound_9b _database_code_depnum_ccdc_archive 'CCDC 627982' _audit_creation_date 22-1-05 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 Cl2 N O3 P Pd' _chemical_formula_sum 'C20 H22 Cl2 N O3 P Pd' _chemical_formula_weight 532.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 8.7850(10) _cell_length_b 28.238(3) _cell_length_c 9.6720(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.84(5) _cell_angle_gamma 90.00 _cell_volume 2177.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18744 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 1.192 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10357 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 30.04 _reflns_number_total 6304 _reflns_number_gt 5046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0574P)^2^+0.1677P] 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 6304 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.003 _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 Pd Pd 0.20311(2) 0.154888(7) 0.80188(2) 0.02892(8) Uani 1 1 d . . . Cl1 Cl 0.10956(10) 0.20173(3) 0.58040(8) 0.04863(18) Uani 1 1 d . . . Cl2 Cl -0.05806(8) 0.12168(3) 0.71675(8) 0.04725(19) Uani 1 1 d . . . P P 0.26102(8) 0.10982(3) 1.00171(7) 0.02993(14) Uani 1 1 d . . . O1 O 0.7178(2) 0.18061(7) 1.05944(19) 0.0374(4) Uani 1 1 d . . . O2 O 0.4410(2) 0.12018(7) 1.13693(19) 0.0353(4) Uani 1 1 d . . . O3 O 0.1315(2) 0.11674(7) 1.0776(2) 0.0368(4) Uani 1 1 d . . . N N 0.4520(2) 0.17607(8) 0.8857(2) 0.0301(4) Uani 1 1 d . . . C1 C 0.5182(5) 0.23098(14) 0.7161(4) 0.0648(10) Uani 1 1 d . . . H1A H 0.5446 0.2556 0.7942 0.097 Uiso 1 1 calc . . . H1B H 0.3999 0.2334 0.6445 0.097 Uiso 1 1 calc . . . H1C H 0.5889 0.2352 0.6611 0.097 Uiso 1 1 calc . . . C2 C 0.5119(4) 0.14227(15) 0.6777(4) 0.0557(9) Uani 1 1 d . . . H2A H 0.5354 0.1119 0.7317 0.084 Uiso 1 1 calc . . . H2B H 0.5816 0.1453 0.6213 0.084 Uiso 1 1 calc . . . H2C H 0.3932 0.1436 0.6063 0.084 Uiso 1 1 calc . . . C3 C 0.5513(3) 0.18242(10) 0.7917(3) 0.0358(6) Uani 1 1 d . . . C4 C 0.7322(4) 0.18023(14) 0.9152(3) 0.0509(8) Uani 1 1 d . . . H4A H 0.7885 0.1510 0.9049 0.061 Uiso 1 1 calc . . . H4B H 0.7974 0.2079 0.9076 0.061 Uiso 1 1 calc . . . C5 C 0.5553(3) 0.17635(9) 1.0264(3) 0.0309(5) Uani 1 1 d . . . C6 C 0.5128(3) 0.16847(11) 1.1612(3) 0.0375(6) Uani 1 1 d . . . C7 C 0.1433(3) 0.08675(11) 1.1988(3) 0.0375(6) Uani 1 1 d . . . C8 C 0.0992(4) 0.10727(12) 1.3063(3) 0.0478(7) Uani 1 1 d . . . H8 H 0.0687 0.1397 1.3002 0.057 Uiso 1 1 calc . . . C9 C 0.1012(5) 0.07851(16) 1.4241(4) 0.0593(10) Uani 1 1 d . . . H9 H 0.0710 0.0915 1.4997 0.071 Uiso 1 1 calc . . . C10 C 0.1453(5) 0.03254(16) 1.4323(4) 0.0650(11) Uani 1 1 d . . . H10 H 0.1458 0.0136 1.5137 0.078 Uiso 1 1 calc . . . C11 C 0.1901(4) 0.01230(14) 1.3235(3) 0.0550(8) Uani 1 1 d . . . H11 H 0.2224 -0.0201 1.3318 0.066 Uiso 1 1 calc . . . C12 C 0.1876(3) 0.03964(11) 1.2018(3) 0.0389(6) Uani 1 1 d . . . C13 C 0.2277(3) 0.01825(10) 1.0800(3) 0.0355(6) Uani 1 1 d . . . C14 C 0.2261(4) -0.03052(11) 1.0570(3) 0.0448(7) Uani 1 1 d . . . H14 H 0.1981 -0.0512 1.1203 0.054 Uiso 1 1 calc . . . C15 C 0.2645(4) -0.04915(11) 0.9442(4) 0.0474(7) Uani 1 1 d . . . H15 H 0.2662 -0.0825 0.9328 0.057 Uiso 1 1 calc . . . C16 C 0.3007(4) -0.01976(12) 0.8467(3) 0.0466(7) Uani 1 1 d . . . H16 H 0.3262 -0.0329 0.7685 0.056 Uiso 1 1 calc . . . C17 C 0.2993(4) 0.02821(11) 0.8643(3) 0.0397(6) Uani 1 1 d . . . H17 H 0.3227 0.0485 0.7972 0.048 Uiso 1 1 calc . . . C18 C 0.2638(3) 0.04768(10) 0.9803(3) 0.0325(5) Uani 1 1 d . . . C19 C 0.3896(4) 0.20496(12) 1.1704(4) 0.0506(8) Uani 1 1 d . . . H19A H 0.3666 0.1982 1.2591 0.076 Uiso 1 1 calc . . . H19B H 0.2849 0.2034 1.0776 0.076 Uiso 1 1 calc . . . H19C H 0.4382 0.2367 1.1803 0.076 Uiso 1 1 calc . . . C20 C 0.6697(4) 0.16509(15) 1.3104(3) 0.0576(9) Uani 1 1 d . . . H20A H 0.6373 0.1596 1.3944 0.086 Uiso 1 1 calc . . . H20B H 0.7332 0.1947 1.3280 0.086 Uiso 1 1 calc . . . H20C H 0.7396 0.1388 1.3048 0.086 Uiso 1 1 calc . . . 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 Pd 0.02721(11) 0.03128(12) 0.02893(11) 0.00114(7) 0.01244(8) 0.00197(7) Cl1 0.0498(4) 0.0452(4) 0.0424(4) 0.0133(3) 0.0110(3) 0.0049(3) Cl2 0.0299(3) 0.0704(5) 0.0410(3) -0.0016(3) 0.0145(3) -0.0077(3) P 0.0308(3) 0.0326(4) 0.0295(3) -0.0005(3) 0.0156(3) -0.0005(3) O1 0.0302(9) 0.0465(12) 0.0356(9) -0.0066(8) 0.0139(7) -0.0046(8) O2 0.0360(10) 0.0371(11) 0.0310(8) 0.0017(7) 0.0122(7) -0.0022(8) O3 0.0410(10) 0.0387(11) 0.0390(9) 0.0015(8) 0.0250(8) 0.0018(8) N 0.0292(10) 0.0326(12) 0.0301(10) 0.0001(8) 0.0140(8) -0.0037(9) C1 0.068(2) 0.059(2) 0.075(2) 0.0233(19) 0.038(2) -0.0054(18) C2 0.0444(18) 0.075(2) 0.0523(18) -0.0239(17) 0.0251(15) -0.0095(17) C3 0.0326(13) 0.0444(16) 0.0345(12) 0.0029(11) 0.0183(11) -0.0029(11) C4 0.0369(15) 0.077(3) 0.0424(15) -0.0058(15) 0.0206(13) -0.0094(16) C5 0.0300(12) 0.0295(13) 0.0342(12) -0.0036(10) 0.0143(10) -0.0021(10) C6 0.0377(14) 0.0440(16) 0.0309(12) -0.0073(11) 0.0145(11) -0.0086(12) C7 0.0360(14) 0.0484(17) 0.0313(12) -0.0028(12) 0.0172(11) -0.0100(12) C8 0.0473(16) 0.062(2) 0.0413(14) -0.0129(14) 0.0251(13) -0.0121(15) C9 0.067(2) 0.083(3) 0.0395(16) -0.0162(17) 0.0338(16) -0.024(2) C10 0.083(3) 0.082(3) 0.0386(15) 0.0014(17) 0.0337(17) -0.021(2) C11 0.067(2) 0.056(2) 0.0459(16) 0.0114(15) 0.0281(16) -0.0063(17) C12 0.0385(14) 0.0446(17) 0.0348(13) 0.0011(12) 0.0166(11) -0.0072(12) C13 0.0345(13) 0.0377(15) 0.0326(12) 0.0000(11) 0.0124(10) -0.0029(11) C14 0.0446(16) 0.0380(16) 0.0504(15) 0.0068(13) 0.0187(13) -0.0002(13) C15 0.0488(17) 0.0328(16) 0.0546(16) -0.0038(13) 0.0159(14) 0.0041(13) C16 0.0455(16) 0.0496(19) 0.0419(14) -0.0092(14) 0.0156(13) 0.0051(14) C17 0.0429(15) 0.0417(17) 0.0371(13) 0.0001(12) 0.0192(12) 0.0036(13) C18 0.0317(12) 0.0331(14) 0.0320(12) -0.0020(10) 0.0126(10) -0.0014(10) C19 0.0607(19) 0.0448(18) 0.0611(18) -0.0194(15) 0.0403(16) -0.0111(15) C20 0.0486(18) 0.088(3) 0.0312(14) -0.0082(15) 0.0125(13) -0.0173(18) _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 Pd N 2.075(2) . ? Pd P 2.1881(8) . ? Pd Cl2 2.2879(10) . ? Pd Cl1 2.3527(9) . ? P O2 1.599(2) . ? P O3 1.6040(17) . ? P C18 1.768(3) . ? O1 C5 1.331(3) . ? O1 C4 1.452(3) . ? O2 C6 1.480(3) . ? O3 C7 1.414(3) . ? N C5 1.280(3) . ? N C3 1.512(3) . ? C1 C3 1.524(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.517(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.536(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.515(3) . ? C6 C20 1.523(4) . ? C6 C19 1.524(4) . ? C7 C8 1.381(4) . ? C7 C12 1.383(4) . ? C8 C9 1.394(5) . ? C8 H8 0.9500 . ? C9 C10 1.347(5) . ? C9 H9 0.9500 . ? C10 C11 1.392(5) . ? C10 H10 0.9500 . ? C11 C12 1.400(4) . ? C11 H11 0.9500 . ? C12 C13 1.492(4) . ? C13 C14 1.394(4) . ? C13 C18 1.406(4) . ? C14 C15 1.375(4) . ? C14 H14 0.9500 . ? C15 C16 1.390(5) . ? C15 H15 0.9500 . ? C16 C17 1.366(4) . ? C16 H16 0.9500 . ? C17 C18 1.398(3) . ? C17 H17 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 N Pd P 90.38(7) . . ? N Pd Cl2 172.52(6) . . ? P Pd Cl2 84.57(5) . . ? N Pd Cl1 95.82(8) . . ? P Pd Cl1 173.70(3) . . ? Cl2 Pd Cl1 89.36(5) . . ? O2 P O3 104.53(9) . . ? O2 P C18 102.70(11) . . ? O3 P C18 102.81(11) . . ? O2 P Pd 113.53(8) . . ? O3 P Pd 112.76(8) . . ? C18 P Pd 118.90(8) . . ? C5 O1 C4 106.6(2) . . ? C6 O2 P 120.50(16) . . ? C7 O3 P 119.14(17) . . ? C5 N C3 107.9(2) . . ? C5 N Pd 125.26(17) . . ? C3 N Pd 125.37(15) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N C3 C2 109.6(2) . . ? N C3 C1 110.7(2) . . ? C2 C3 C1 112.6(3) . . ? N C3 C4 101.38(19) . . ? C2 C3 C4 112.4(3) . . ? C1 C3 C4 109.6(3) . . ? O1 C4 C3 105.5(2) . . ? O1 C4 H4A 110.6 . . ? C3 C4 H4A 110.6 . . ? O1 C4 H4B 110.6 . . ? C3 C4 H4B 110.6 . . ? H4A C4 H4B 108.8 . . ? N C5 O1 117.8(2) . . ? N C5 C6 126.4(2) . . ? O1 C5 C6 115.7(2) . . ? O2 C6 C5 104.0(2) . . ? O2 C6 C20 104.4(2) . . ? C5 C6 C20 111.9(2) . . ? O2 C6 C19 111.5(2) . . ? C5 C6 C19 112.9(2) . . ? C20 C6 C19 111.7(3) . . ? C8 C7 C12 123.6(3) . . ? C8 C7 O3 115.3(3) . . ? C12 C7 O3 121.1(2) . . ? C7 C8 C9 117.4(3) . . ? C7 C8 H8 121.3 . . ? C9 C8 H8 121.3 . . ? C10 C9 C8 120.9(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 121.1(3) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C7 C12 C11 117.0(3) . . ? C7 C12 C13 122.0(2) . . ? C11 C12 C13 121.0(3) . . ? C14 C13 C18 117.7(2) . . ? C14 C13 C12 122.4(2) . . ? C18 C13 C12 119.9(3) . . ? C15 C14 C13 121.0(3) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 120.8(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 119.4(3) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.4(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C13 120.6(3) . . ? C17 C18 P 120.2(2) . . ? C13 C18 P 119.22(19) . . ? C6 C19 H19A 109.5 . . ? C6 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C6 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C6 C20 H20A 109.5 . . ? C6 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C6 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 N Pd P O2 13.36(10) . . . . ? Cl2 Pd P O2 -172.18(8) . . . . ? Cl1 Pd P O2 -156.4(3) . . . . ? N Pd P O3 132.00(10) . . . . ? Cl2 Pd P O3 -53.53(8) . . . . ? Cl1 Pd P O3 -37.8(3) . . . . ? N Pd P C18 -107.59(12) . . . . ? Cl2 Pd P C18 66.87(10) . . . . ? Cl1 Pd P C18 82.6(3) . . . . ? O3 P O2 C6 -91.74(18) . . . . ? C18 P O2 C6 161.21(17) . . . . ? Pd P O2 C6 31.53(18) . . . . ? O2 P O3 C7 -62.2(2) . . . . ? C18 P O3 C7 44.7(2) . . . . ? Pd P O3 C7 173.99(16) . . . . ? P Pd N C5 -25.4(2) . . . . ? Cl2 Pd N C5 -73.0(5) . . . . ? Cl1 Pd N C5 153.4(2) . . . . ? P Pd N C3 139.2(2) . . . . ? Cl2 Pd N C3 91.7(4) . . . . ? Cl1 Pd N C3 -41.9(2) . . . . ? C5 N C3 C2 125.3(3) . . . . ? Pd N C3 C2 -41.6(3) . . . . ? C5 N C3 C1 -109.9(3) . . . . ? Pd N C3 C1 83.2(3) . . . . ? C5 N C3 C4 6.3(3) . . . . ? Pd N C3 C4 -160.5(2) . . . . ? C5 O1 C4 C3 8.0(3) . . . . ? N C3 C4 O1 -8.5(3) . . . . ? C2 C3 C4 O1 -125.4(3) . . . . ? C1 C3 C4 O1 108.5(3) . . . . ? C3 N C5 O1 -1.6(3) . . . . ? Pd N C5 O1 165.28(18) . . . . ? C3 N C5 C6 -176.5(3) . . . . ? Pd N C5 C6 -9.6(4) . . . . ? C4 O1 C5 N -4.3(3) . . . . ? C4 O1 C5 C6 171.1(2) . . . . ? P O2 C6 C5 -70.2(2) . . . . ? P O2 C6 C20 172.41(19) . . . . ? P O2 C6 C19 51.7(3) . . . . ? N C5 C6 O2 60.7(3) . . . . ? O1 C5 C6 O2 -114.3(2) . . . . ? N C5 C6 C20 172.8(3) . . . . ? O1 C5 C6 C20 -2.2(4) . . . . ? N C5 C6 C19 -60.3(4) . . . . ? O1 C5 C6 C19 124.7(3) . . . . ? P O3 C7 C8 147.4(2) . . . . ? P O3 C7 C12 -35.9(3) . . . . ? C12 C7 C8 C9 0.4(5) . . . . ? O3 C7 C8 C9 177.0(3) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 C11 -0.1(6) . . . . ? C9 C10 C11 C12 -0.9(6) . . . . ? C8 C7 C12 C11 -1.3(4) . . . . ? O3 C7 C12 C11 -177.7(2) . . . . ? C8 C7 C12 C13 177.4(3) . . . . ? O3 C7 C12 C13 1.0(4) . . . . ? C10 C11 C12 C7 1.5(5) . . . . ? C10 C11 C12 C13 -177.2(3) . . . . ? C7 C12 C13 C14 -161.5(3) . . . . ? C11 C12 C13 C14 17.2(4) . . . . ? C7 C12 C13 C18 16.5(4) . . . . ? C11 C12 C13 C18 -164.8(3) . . . . ? C18 C13 C14 C15 2.3(4) . . . . ? C12 C13 C14 C15 -179.7(3) . . . . ? C13 C14 C15 C16 -2.1(5) . . . . ? C14 C15 C16 C17 0.5(5) . . . . ? C15 C16 C17 C18 0.7(5) . . . . ? C16 C17 C18 C13 -0.4(4) . . . . ? C16 C17 C18 P -179.6(2) . . . . ? C14 C13 C18 C17 -1.1(4) . . . . ? C12 C13 C18 C17 -179.1(2) . . . . ? C14 C13 C18 P 178.1(2) . . . . ? C12 C13 C18 P 0.1(3) . . . . ? O2 P C18 C17 -99.6(2) . . . . ? O3 P C18 C17 152.1(2) . . . . ? Pd P C18 C17 26.7(2) . . . . ? O2 P C18 C13 81.2(2) . . . . ? O3 P C18 C13 -27.2(2) . . . . ? Pd P C18 C13 -152.51(17) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.728 _refine_diff_density_min -0.983 _refine_diff_density_rms 0.207