# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Teck-Peng Loh' _publ_contact_author_email Teckpeng@ntu.edu.sg loop_ _publ_author_name 'Yun-He Xu' 'Teck-Peng Loh' data_ltp196s _database_code_depnum_ccdc_archive 'CCDC 806122' #TrackingRef '- ltp196s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common LTP196 _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cl N O2 Pd S' _chemical_formula_sum 'C16 H18 Cl N O2 Pd S' _chemical_formula_weight 430.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 P2(1)/c 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 13.4450(7) _cell_length_b 9.4054(5) _cell_length_c 14.8518(7) _cell_angle_alpha 90.00 _cell_angle_beta 117.218(4) _cell_angle_gamma 90.00 _cell_volume 1670.14(15) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 8128 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 31.06 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8069 _exptl_absorpt_correction_T_max 0.8726 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22627 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 31.08 _reflns_number_total 5333 _reflns_number_gt 4588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0279P)^2^+1.2069P] 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 5333 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0637 _refine_ls_wR_factor_gt 0.0598 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.862583(12) 0.542576(14) 0.287986(10) 0.01368(4) Uani 1 1 d . . . C1 C 0.78528(17) 0.54350(19) 0.37201(15) 0.0171(3) Uani 1 1 d . . . H1 H 0.7195 0.4874 0.3499 0.021 Uiso 1 1 calc R . . C2 C 0.81747(16) 0.61661(19) 0.45798(14) 0.0155(3) Uani 1 1 d . . . C3 C 0.74799(16) 0.62432(19) 0.51206(14) 0.0172(3) Uani 1 1 d . . . C4 C 0.63056(17) 0.6437(2) 0.45513(16) 0.0207(4) Uani 1 1 d . . . H4 H 0.5981 0.6514 0.3835 0.025 Uiso 1 1 calc R . . C5 C 0.56333(17) 0.6515(2) 0.50208(16) 0.0216(4) Uani 1 1 d . . . H5 H 0.4853 0.6671 0.4628 0.026 Uiso 1 1 calc R . . C6 C 0.60909(17) 0.6367(2) 0.60789(16) 0.0201(4) Uani 1 1 d . . . C7 C 0.54145(18) 0.6370(2) 0.65901(17) 0.0249(4) Uani 1 1 d . . . H7 H 0.4633 0.6539 0.6219 0.030 Uiso 1 1 calc R . . C8 C 0.5879(2) 0.6131(2) 0.76049(18) 0.0291(5) Uani 1 1 d . . . H8 H 0.5418 0.6111 0.7935 0.035 Uiso 1 1 calc R . . C9 C 0.7039(2) 0.5913(2) 0.81690(17) 0.0272(4) Uani 1 1 d . . . H9 H 0.7352 0.5744 0.8877 0.033 Uiso 1 1 calc R . . C10 C 0.77221(18) 0.5941(2) 0.77139(15) 0.0216(4) Uani 1 1 d . . . H10 H 0.8506 0.5814 0.8106 0.026 Uiso 1 1 calc R . . C11 C 0.72575(17) 0.61613(19) 0.66552(14) 0.0185(4) Uani 1 1 d . . . C12 C 0.79454(17) 0.61210(19) 0.61544(15) 0.0185(4) Uani 1 1 d . . . H12 H 0.8732 0.6009 0.6540 0.022 Uiso 1 1 calc R . . C13 C 0.99535(16) 0.71241(19) 0.47404(14) 0.0160(3) Uani 1 1 d . . . C14 C 1.09470(16) 0.8037(2) 0.53692(14) 0.0188(4) Uani 1 1 d . . . H14A H 1.0975 0.8843 0.4963 0.028 Uiso 1 1 calc R . . H14B H 1.1632 0.7473 0.5594 0.028 Uiso 1 1 calc R . . H14C H 1.0882 0.8390 0.5961 0.028 Uiso 1 1 calc R . . C15 C 0.79104(18) 0.2537(2) 0.15371(15) 0.0211(4) Uani 1 1 d . . . H15A H 0.7352 0.2016 0.0953 0.032 Uiso 1 1 calc R . . H15B H 0.8202 0.1921 0.2135 0.032 Uiso 1 1 calc R . . H15C H 0.8525 0.2832 0.1397 0.032 Uiso 1 1 calc R . . C16 C 0.66908(19) 0.4894(2) 0.05573(16) 0.0273(4) Uani 1 1 d . . . H16A H 0.6273 0.5740 0.0571 0.041 Uiso 1 1 calc R . . H16B H 0.6184 0.4229 0.0045 0.041 Uiso 1 1 calc R . . H16C H 0.7289 0.5173 0.0390 0.041 Uiso 1 1 calc R . . Cl1 Cl 0.95175(4) 0.55893(5) 0.17808(3) 0.01767(9) Uani 1 1 d . . . N1 N 0.91765(13) 0.69714(16) 0.50557(12) 0.0162(3) Uani 1 1 d . . . H1A H 0.9297 0.7416 0.5618 0.019 Uiso 1 1 d R . . O1 O 0.99034(11) 0.65709(14) 0.39537(10) 0.0179(3) Uani 1 1 d . . . O2 O 0.63585(13) 0.35798(18) 0.19578(12) 0.0291(4) Uani 1 1 d . . . S1 S 0.72823(4) 0.40597(5) 0.17642(3) 0.01617(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 Pd1 0.01647(7) 0.01356(7) 0.01563(7) -0.00134(5) 0.01133(5) -0.00129(5) C1 0.0199(9) 0.0171(8) 0.0217(9) -0.0015(7) 0.0158(8) -0.0027(7) C2 0.0190(9) 0.0148(8) 0.0184(8) 0.0015(6) 0.0136(7) -0.0003(6) C3 0.0248(10) 0.0120(7) 0.0225(9) -0.0014(6) 0.0174(8) -0.0021(7) C4 0.0246(10) 0.0176(8) 0.0249(9) -0.0022(7) 0.0154(8) -0.0028(7) C5 0.0199(9) 0.0191(9) 0.0285(10) -0.0027(7) 0.0134(8) -0.0011(7) C6 0.0235(10) 0.0139(8) 0.0284(10) -0.0047(7) 0.0165(8) -0.0034(7) C7 0.0234(10) 0.0240(10) 0.0347(11) -0.0056(8) 0.0198(9) -0.0053(8) C8 0.0348(12) 0.0292(11) 0.0367(12) -0.0081(9) 0.0279(11) -0.0072(9) C9 0.0395(13) 0.0253(10) 0.0258(10) -0.0028(8) 0.0228(10) -0.0046(9) C10 0.0273(10) 0.0203(9) 0.0232(9) -0.0002(7) 0.0166(9) -0.0008(8) C11 0.0278(10) 0.0121(8) 0.0208(9) -0.0016(6) 0.0158(8) -0.0020(7) C12 0.0242(10) 0.0146(8) 0.0224(9) 0.0000(7) 0.0156(8) -0.0006(7) C13 0.0203(9) 0.0156(8) 0.0160(8) 0.0020(6) 0.0115(7) 0.0007(7) C14 0.0198(9) 0.0217(9) 0.0173(8) -0.0024(7) 0.0107(7) -0.0036(7) C15 0.0258(10) 0.0146(8) 0.0241(9) -0.0017(7) 0.0124(8) 0.0026(7) C16 0.0263(11) 0.0236(10) 0.0243(10) 0.0046(8) 0.0048(9) 0.0040(8) Cl1 0.0206(2) 0.0201(2) 0.01809(19) -0.00021(15) 0.01386(18) -0.00108(16) N1 0.0202(8) 0.0172(7) 0.0157(7) -0.0019(6) 0.0121(6) -0.0012(6) O1 0.0195(7) 0.0211(6) 0.0177(6) -0.0033(5) 0.0127(5) -0.0037(5) O2 0.0264(8) 0.0336(8) 0.0389(9) -0.0162(7) 0.0249(7) -0.0140(6) S1 0.0172(2) 0.01535(19) 0.0200(2) -0.00295(16) 0.01196(18) -0.00107(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 C1 1.9555(18) . ? Pd1 O1 2.0367(13) . ? Pd1 S1 2.2184(5) . ? Pd1 Cl1 2.4322(5) . ? C1 C2 1.336(3) . ? C1 H1 0.9500 . ? C2 N1 1.420(2) . ? C2 C3 1.486(2) . ? C3 C12 1.372(3) . ? C3 C4 1.421(3) . ? C4 C5 1.373(3) . ? C4 H4 0.9500 . ? C5 C6 1.408(3) . ? C5 H5 0.9500 . ? C6 C11 1.415(3) . ? C6 C7 1.427(3) . ? C7 C8 1.361(3) . ? C7 H7 0.9500 . ? C8 C9 1.408(3) . ? C8 H8 0.9500 . ? C9 C10 1.367(3) . ? C9 H9 0.9500 . ? C10 C11 1.417(3) . ? C10 H10 0.9500 . ? C11 C12 1.428(3) . ? C12 H12 0.9500 . ? C13 O1 1.252(2) . ? C13 N1 1.334(2) . ? C13 C14 1.501(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 S1 1.7716(19) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 S1 1.777(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 H1A 0.8800 . ? O2 S1 1.4683(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 O1 90.11(7) . . ? C1 Pd1 S1 89.45(6) . . ? O1 Pd1 S1 176.51(4) . . ? C1 Pd1 Cl1 175.56(6) . . ? O1 Pd1 Cl1 89.66(4) . . ? S1 Pd1 Cl1 91.045(17) . . ? C2 C1 Pd1 125.30(14) . . ? C2 C1 H1 117.4 . . ? Pd1 C1 H1 117.4 . . ? C1 C2 N1 124.69(16) . . ? C1 C2 C3 122.18(17) . . ? N1 C2 C3 113.11(15) . . ? C12 C3 C4 119.37(17) . . ? C12 C3 C2 121.52(18) . . ? C4 C3 C2 119.11(17) . . ? C5 C4 C3 121.00(19) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.56(19) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C11 119.09(18) . . ? C5 C6 C7 122.30(19) . . ? C11 C6 C7 118.57(19) . . ? C8 C7 C6 120.5(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.36(19) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 121.0(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 119.8(2) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C6 C11 C10 119.70(18) . . ? C6 C11 C12 119.42(17) . . ? C10 C11 C12 120.82(19) . . ? C3 C12 C11 120.53(19) . . ? C3 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? O1 C13 N1 124.50(18) . . ? O1 C13 C14 118.10(16) . . ? N1 C13 C14 117.40(16) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? S1 C15 H15A 109.5 . . ? S1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S1 C16 H16A 109.5 . . ? S1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 N1 C2 126.84(16) . . ? C13 N1 H1A 116.6 . . ? C2 N1 H1A 116.5 . . ? C13 O1 Pd1 128.06(12) . . ? O2 S1 C15 107.96(10) . . ? O2 S1 C16 107.76(11) . . ? C15 S1 C16 101.38(10) . . ? O2 S1 Pd1 120.30(6) . . ? C15 S1 Pd1 108.31(7) . . ? C16 S1 Pd1 109.49(8) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 31.08 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.880 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.095 # Attachment '- ltp198.cif' data_ltp198 _database_code_depnum_ccdc_archive 'CCDC 806123' #TrackingRef '- ltp198.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common LTP198 _chemical_melting_point ? _chemical_formula_moiety 'C18 H21 N O4 Pd S, 0.5(C4 H10 O)' _chemical_formula_sum 'C20 H26 N O4.50 Pd S' _chemical_formula_weight 490.88 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 13.1411(6) _cell_length_b 18.9878(10) _cell_length_c 8.6250(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.879(2) _cell_angle_gamma 90.00 _cell_volume 2059.40(17) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 5916 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 28.38 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1004 _exptl_absorpt_coefficient_mu 1.030 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6834 _exptl_absorpt_correction_T_max 0.9221 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19039 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.68 _reflns_number_total 5259 _reflns_number_gt 4223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0158P)^2^+4.2107P] 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 5259 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0744 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.499462(17) 0.552957(11) 0.29139(3) 0.01278(6) Uani 1 1 d . . . C1 C 0.6026(2) 0.60274(15) 0.2067(3) 0.0155(6) Uani 1 1 d . . . H1 H 0.6099 0.6520 0.2258 0.019 Uiso 1 1 calc R . . C2 C 0.6636(2) 0.57327(15) 0.1244(3) 0.0148(6) Uani 1 1 d . . . C3 C 0.7376(2) 0.61560(15) 0.0590(3) 0.0153(6) Uani 1 1 d . . . C4 C 0.7000(2) 0.67896(16) -0.0257(4) 0.0184(6) Uani 1 1 d . . . H4 H 0.6285 0.6934 -0.0410 0.022 Uiso 1 1 calc R . . C5 C 0.7665(2) 0.71953(17) -0.0856(4) 0.0209(6) Uani 1 1 d . . . H5 H 0.7401 0.7616 -0.1427 0.025 Uiso 1 1 calc R . . C6 C 0.8735(2) 0.69973(17) -0.0636(4) 0.0204(6) Uani 1 1 d . . . C7 C 0.9426(3) 0.73961(19) -0.1289(4) 0.0297(8) Uani 1 1 d . . . H7 H 0.9175 0.7811 -0.1893 0.036 Uiso 1 1 calc R . . C8 C 1.0449(3) 0.7184(2) -0.1052(5) 0.0414(10) Uani 1 1 d . . . H8 H 1.0907 0.7455 -0.1493 0.050 Uiso 1 1 calc R . . C9 C 1.0840(3) 0.6571(2) -0.0166(5) 0.0400(10) Uani 1 1 d . . . H9 H 1.1561 0.6438 0.0005 0.048 Uiso 1 1 calc R . . C10 C 1.0191(3) 0.61641(19) 0.0453(5) 0.0310(8) Uani 1 1 d . . . H10 H 1.0459 0.5747 0.1038 0.037 Uiso 1 1 calc R . . C11 C 0.9112(2) 0.63685(17) 0.0218(4) 0.0206(6) Uani 1 1 d . . . C12 C 0.8405(2) 0.59528(16) 0.0810(4) 0.0195(6) Uani 1 1 d . . . H12 H 0.8653 0.5526 0.1367 0.023 Uiso 1 1 calc R . . C13 C 0.6130(2) 0.44918(16) 0.1415(3) 0.0148(5) Uani 1 1 d . . . C14 C 0.6331(2) 0.37495(15) 0.0993(4) 0.0184(6) Uani 1 1 d . . . H14A H 0.6856 0.3531 0.1913 0.028 Uiso 1 1 calc R . . H14B H 0.6602 0.3750 0.0047 0.028 Uiso 1 1 calc R . . H14C H 0.5665 0.3482 0.0741 0.028 Uiso 1 1 calc R . . C15 C 0.2890(2) 0.49676(15) 0.2890(4) 0.0168(6) Uani 1 1 d . . . C16 C 0.2156(2) 0.45131(18) 0.3524(4) 0.0250(7) Uani 1 1 d . . . H16A H 0.1469 0.4751 0.3340 0.037 Uiso 1 1 calc R . . H16B H 0.2472 0.4434 0.4688 0.037 Uiso 1 1 calc R . . H16C H 0.2051 0.4060 0.2957 0.037 Uiso 1 1 calc R . . C17 C 0.3388(2) 0.65159(17) 0.4395(4) 0.0222(7) Uani 1 1 d . . . H17A H 0.3312 0.6953 0.4955 0.033 Uiso 1 1 calc R . . H17B H 0.3426 0.6115 0.5125 0.033 Uiso 1 1 calc R . . H17C H 0.2775 0.6459 0.3434 0.033 Uiso 1 1 calc R . . C18 C 0.5504(3) 0.67115(16) 0.5698(4) 0.0217(6) Uani 1 1 d . . . H18A H 0.6216 0.6761 0.5560 0.033 Uiso 1 1 calc R . . H18B H 0.5500 0.6316 0.6426 0.033 Uiso 1 1 calc R . . H18C H 0.5316 0.7146 0.6163 0.033 Uiso 1 1 calc R . . C19 C 0.0834(9) 0.6144(5) 0.5383(13) 0.046(2) Uani 0.50 1 d P A -1 H19A H 0.0952 0.6134 0.4312 0.070 Uiso 0.50 1 calc PR A -1 H19B H 0.1436 0.6377 0.6156 0.070 Uiso 0.50 1 calc PR A -1 H19C H 0.0179 0.6404 0.5319 0.070 Uiso 0.50 1 calc PR A -1 C20 C 0.0736(6) 0.5410(4) 0.5932(9) 0.0327(16) Uani 0.50 1 d P A -1 H20A H 0.1423 0.5161 0.6121 0.039 Uiso 0.50 1 calc PR A -1 H20B H 0.0546 0.5417 0.6962 0.039 Uiso 0.50 1 calc PR A -1 O5 O -0.0073(11) 0.5052(8) 0.4708(10) 0.0317(17) Uani 0.50 1 d P A -1 C21 C -0.0187(6) 0.4337(4) 0.5100(10) 0.0370(18) Uani 0.50 1 d P A -1 H21A H -0.0300 0.4302 0.6183 0.044 Uiso 0.50 1 calc PR A -1 H21B H 0.0461 0.4068 0.5114 0.044 Uiso 0.50 1 calc PR A -1 C22 C -0.1117(8) 0.4053(6) 0.3847(12) 0.046(2) Uani 0.50 1 d P A -1 H22A H -0.1763 0.4291 0.3919 0.070 Uiso 0.50 1 calc PR A -1 H22B H -0.1177 0.3547 0.4020 0.070 Uiso 0.50 1 calc PR A -1 H22C H -0.1026 0.4134 0.2773 0.070 Uiso 0.50 1 calc PR A -1 N1 N 0.66608(19) 0.49995(13) 0.0921(3) 0.0154(5) Uani 1 1 d . . . H1A H 0.7072 0.4867 0.0329 0.019 Uiso 1 1 calc R . . O1 O 0.54944(16) 0.45941(10) 0.2236(2) 0.0159(4) Uani 1 1 d . . . O2 O 0.38773(15) 0.49436(11) 0.3704(2) 0.0164(4) Uani 1 1 d . . . O3 O 0.25204(16) 0.53297(11) 0.1647(2) 0.0192(4) Uani 1 1 d . . . O4 O 0.45106(19) 0.71866(11) 0.2778(3) 0.0241(5) Uani 1 1 d . . . S1 S 0.45710(6) 0.65533(4) 0.37953(8) 0.01528(14) 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 Pd1 0.01632(11) 0.01033(10) 0.01322(10) -0.00038(9) 0.00668(8) -0.00004(9) C1 0.0181(14) 0.0127(14) 0.0163(14) -0.0013(11) 0.0062(11) -0.0019(11) C2 0.0163(14) 0.0118(13) 0.0147(13) 0.0014(11) 0.0022(11) -0.0001(11) C3 0.0172(14) 0.0145(14) 0.0159(14) -0.0019(11) 0.0074(11) -0.0016(11) C4 0.0179(15) 0.0186(15) 0.0196(15) -0.0008(12) 0.0070(12) 0.0016(12) C5 0.0237(16) 0.0192(15) 0.0194(15) 0.0060(12) 0.0055(12) 0.0010(12) C6 0.0200(15) 0.0231(16) 0.0193(15) 0.0015(12) 0.0076(12) -0.0022(12) C7 0.0288(18) 0.0292(19) 0.0340(19) 0.0086(15) 0.0136(15) -0.0032(15) C8 0.030(2) 0.049(3) 0.052(3) 0.013(2) 0.0234(18) -0.0044(18) C9 0.0204(17) 0.048(2) 0.057(3) 0.011(2) 0.0195(17) 0.0063(17) C10 0.0219(17) 0.0296(19) 0.044(2) 0.0043(16) 0.0143(16) 0.0020(14) C11 0.0196(15) 0.0208(16) 0.0234(16) -0.0002(13) 0.0095(12) -0.0015(12) C12 0.0214(15) 0.0145(15) 0.0234(16) 0.0007(12) 0.0075(12) 0.0002(12) C13 0.0157(13) 0.0152(13) 0.0122(12) -0.0013(11) 0.0023(10) 0.0003(12) C14 0.0225(15) 0.0131(14) 0.0213(15) 0.0006(12) 0.0089(12) 0.0027(12) C15 0.0209(15) 0.0142(14) 0.0183(14) -0.0050(11) 0.0106(12) 0.0006(11) C16 0.0212(15) 0.0301(18) 0.0244(16) 0.0022(14) 0.0080(13) -0.0051(14) C17 0.0262(16) 0.0201(16) 0.0255(16) -0.0027(13) 0.0158(13) 0.0001(13) C18 0.0293(17) 0.0145(15) 0.0220(15) -0.0021(12) 0.0085(13) 0.0015(13) C19 0.051(6) 0.042(6) 0.045(6) 0.006(5) 0.010(5) -0.009(5) C20 0.029(4) 0.037(5) 0.031(4) 0.006(3) 0.007(3) -0.001(3) O5 0.023(4) 0.038(5) 0.026(6) 0.008(5) -0.005(5) 0.012(3) C21 0.029(4) 0.041(5) 0.041(4) 0.015(4) 0.011(3) 0.009(3) C22 0.052(6) 0.041(6) 0.040(6) 0.009(5) 0.003(5) 0.004(5) N1 0.0196(12) 0.0139(12) 0.0151(12) -0.0013(9) 0.0089(10) 0.0013(10) O1 0.0197(10) 0.0129(10) 0.0174(10) -0.0006(8) 0.0088(8) -0.0003(8) O2 0.0174(10) 0.0150(10) 0.0183(10) 0.0028(8) 0.0074(8) 0.0007(8) O3 0.0205(11) 0.0186(11) 0.0186(10) 0.0006(8) 0.0059(8) 0.0026(8) O4 0.0417(14) 0.0128(10) 0.0228(11) 0.0048(9) 0.0169(10) 0.0059(10) S1 0.0214(4) 0.0108(3) 0.0162(3) -0.0001(3) 0.0096(3) 0.0006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 C1 1.959(3) . ? Pd1 O1 2.0376(19) . ? Pd1 O2 2.1068(19) . ? Pd1 S1 2.2163(7) . ? C1 C2 1.338(4) . ? C1 H1 0.9500 . ? C2 N1 1.422(4) . ? C2 C3 1.493(4) . ? C3 C12 1.366(4) . ? C3 C4 1.420(4) . ? C4 C5 1.373(4) . ? C4 H4 0.9500 . ? C5 C6 1.414(4) . ? C5 H5 0.9500 . ? C6 C11 1.415(4) . ? C6 C7 1.419(4) . ? C7 C8 1.361(5) . ? C7 H7 0.9500 . ? C8 C9 1.405(6) . ? C8 H8 0.9500 . ? C9 C10 1.369(5) . ? C9 H9 0.9500 . ? C10 C11 1.427(4) . ? C10 H10 0.9500 . ? C11 C12 1.422(4) . ? C12 H12 0.9500 . ? C13 O1 1.257(3) . ? C13 N1 1.330(4) . ? C13 C14 1.498(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O3 1.248(4) . ? C15 O2 1.284(3) . ? C15 C16 1.510(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 S1 1.776(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 S1 1.766(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.489(12) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O5 1.434(16) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? O5 C21 1.417(16) . ? C21 C22 1.478(13) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 H1A 0.8800 . ? O4 S1 1.477(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 O1 89.90(10) . . ? C1 Pd1 O2 176.21(10) . . ? O1 Pd1 O2 86.87(8) . . ? C1 Pd1 S1 88.53(9) . . ? O1 Pd1 S1 175.59(6) . . ? O2 Pd1 S1 94.83(6) . . ? C2 C1 Pd1 125.6(2) . . ? C2 C1 H1 117.2 . . ? Pd1 C1 H1 117.2 . . ? C1 C2 N1 124.4(3) . . ? C1 C2 C3 122.1(3) . . ? N1 C2 C3 113.4(2) . . ? C12 C3 C4 119.6(3) . . ? C12 C3 C2 121.5(3) . . ? C4 C3 C2 118.9(2) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C11 118.6(3) . . ? C5 C6 C7 122.1(3) . . ? C11 C6 C7 119.3(3) . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 121.1(3) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C6 C11 C12 119.3(3) . . ? C6 C11 C10 119.1(3) . . ? C12 C11 C10 121.6(3) . . ? C3 C12 C11 121.1(3) . . ? C3 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? O1 C13 N1 124.4(3) . . ? O1 C13 C14 118.3(3) . . ? N1 C13 C14 117.3(2) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C15 O2 124.7(3) . . ? O3 C15 C16 119.7(3) . . ? O2 C15 C16 115.6(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? S1 C17 H17A 109.5 . . ? S1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? S1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? S1 C18 H18A 109.5 . . ? S1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C20 C19 108.9(8) . . ? O5 C20 H20A 109.9 . . ? C19 C20 H20A 109.9 . . ? O5 C20 H20B 109.9 . . ? C19 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? C21 O5 C20 112.7(6) . . ? O5 C21 C22 107.3(8) . . ? O5 C21 H21A 110.3 . . ? C22 C21 H21A 110.3 . . ? O5 C21 H21B 110.3 . . ? C22 C21 H21B 110.3 . . ? H21A C21 H21B 108.5 . . ? C13 N1 C2 127.0(2) . . ? C13 N1 H1A 116.5 . . ? C2 N1 H1A 116.5 . . ? C13 O1 Pd1 128.21(19) . . ? C15 O2 Pd1 119.53(18) . . ? O4 S1 C18 108.45(14) . . ? O4 S1 C17 107.74(14) . . ? C18 S1 C17 99.61(15) . . ? O4 S1 Pd1 119.07(9) . . ? C18 S1 Pd1 106.98(10) . . ? C17 S1 Pd1 113.14(11) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.68 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.678 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.107