# Electronic Supplementary Material (ESI) for Catalysis Science & Technology # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Cat.Sci.Tech. _journal_coden_cambridge 1486 #TrackingRef '- 13_14.cif' #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Josefina D\'iez Departamento de Qu\'imica Org\'anica e Inorg\'anica Facultad de Qu\'imica Universidad de Oviedo Avda. Juli\'an Claver\'ia, 8 33071 Oviedo Spain ; _publ_contact_author_phone '0034 98 5102960' _publ_contact_author_fax '0034 98 5103446' _publ_contact_author_email jdv@uniovi.es _publ_requested_coeditor_name ? _publ_contact_letter ; Oviedo 07/06/2011 Please receive the CIF for compounds 13 and 14 submitted to be published in Catalysis Science & Technology Thank you very much. J. D\'iez. ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Conjugate addition of arylboronic acids to \a,\b-unsaturated carbonyl compounds in aqueous medium using Pd(II) complexes with dihydroxy-2,2'-bipyridine ligands: Homogeneous or heterogeneous nano-catalysis?. ; _publ_section_abstract ; The conjugate addition of arylboronic acids to \a,\b-unsaturated carbonyl compounds in water under air has been studied using a series of palladium(II) derivatives containing symmetrically disubstituted-2,2'-bipyridine ligands. Among them, best results were obtained with complex [PdCl2{3,3'-(OH)2-2,2'-bipy}] (2a), which selectively provides the desired addition products in good to high yields under mild conditions. Catalytically active palladium nanoparticles are formed in the course of the reactions. In the presence of sodium dodecyl sulfate (SDS) these nanoparticles can be stabilized and recycled. ; # The loop structure below should contain the names and addresses of all #authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address E.Tomas-Mendivil ; Departamento de Qu\'imica Org\'anica e Inorg\'anica Facultad de Qu\'imica Universidad de Oviedo Avda. Juli\'an Claver\'ia, 8 33006 Oviedo Spain ; J.Diez ; Departamento de Qu\'imica Org\'anica e Inorg\'anica Facultad de Qu\'imica Universidad de Oviedo Avda. Juli\'an Claver\'ia, 8 33006 Oviedo Spain ; 'Victorio Cadierno' ; Departamento de Qu\'imica Org\'anica e Inorg\'anica Facultad de Qu\'imica Universidad de Oviedo Avda. Juli\'an Claver\'ia, 8 33006 Oviedo Spain ; _publ_contact_author_name 'Josefina Diez' #=============================================================================== data_13 _database_code_depnum_ccdc_archive 'CCDC 828891' #TrackingRef '- 13_14.cif' #=============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Cl2 N2 O2 Pd, 2(C2 H6 O S)' _chemical_formula_sum 'C16 H24 Cl2 N2 O4 Pd S2' _chemical_formula_weight 549.79 _chemical_compound_source synthesis loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4783(3) _cell_length_b 11.6061(4) _cell_length_c 13.1535(5) _cell_angle_alpha 67.125(4) _cell_angle_beta 89.797(3) _cell_angle_gamma 68.971(4) _cell_volume 1099.10(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9334 _cell_measurement_theta_min 3.4315 _cell_measurement_theta_max 73.7603 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.214 _exptl_crystal_size_mid 0.079 _exptl_crystal_size_min 0.034 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 11.034 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.30419 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CCD _diffrn_measurement_device_type 'Xcalibur, Onyx, Nova' _diffrn_detector_area_resol_mean 8.2640 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11501 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 73.88 _reflns_number_total 4216 _reflns_number_gt 3966 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SIR2004(Burla, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2007)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0507P)^2^+0.7398P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4216 _refine_ls_number_parameters 349 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.067 _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 C1 C 0.8872(4) 0.6347(3) 0.6879(3) 0.0498(7) Uani 1 1 d . . . C2 C 0.8001(5) 0.7736(3) 0.6344(3) 0.0529(7) Uani 1 1 d . . . C3 C 0.8417(4) 0.8458(3) 0.5339(3) 0.0477(7) Uani 1 1 d . . . C11 C 0.7463(6) 0.9970(3) 0.4691(3) 0.0646(10) Uani 1 1 d D . . C4 C 0.9716(4) 0.7741(3) 0.4914(3) 0.0449(6) Uani 1 1 d . . . C5 C 1.0555(4) 0.6350(3) 0.5483(2) 0.0396(6) Uani 1 1 d . . . C6 C 1.1918(4) 0.5510(3) 0.5068(2) 0.0397(6) Uani 1 1 d . . . C7 C 1.2500(4) 0.6012(3) 0.4084(2) 0.0441(6) Uani 1 1 d . . . C8 C 1.3770(4) 0.5136(3) 0.3751(3) 0.0449(6) Uani 1 1 d . . . C12 C 1.4389(5) 0.5674(4) 0.2660(3) 0.0545(8) Uani 1 1 d . . . C9 C 1.4397(5) 0.3763(3) 0.4449(3) 0.0507(7) Uani 1 1 d . . . C10 C 1.3765(4) 0.3313(3) 0.5423(3) 0.0481(7) Uani 1 1 d . . . C13 C 0.2060(9) 0.9654(5) 0.1043(4) 0.0869(15) Uani 1 1 d . . . C14 C -0.0857(10) 1.1153(8) 0.1479(7) 0.116(2) Uani 1 1 d . . . C15 C 0.7599(7) 0.5198(6) 0.0190(5) 0.0891(14) Uani 1 1 d D . . C16 C 0.5468(8) 0.7730(6) -0.0212(5) 0.0945(17) Uani 1 1 d D . . N1 N 1.0129(3) 0.5653(2) 0.6460(2) 0.0411(5) Uani 1 1 d . . . N2 N 1.2544(3) 0.4157(2) 0.5742(2) 0.0418(5) Uani 1 1 d . . . O1 O 0.6397(4) 1.0599(3) 0.5296(3) 0.0800(9) Uani 1 1 d D . . O2 O 1.5846(4) 0.4707(4) 0.2517(3) 0.0737(8) Uani 1 1 d . . . O3 O 0.1705(5) 0.9364(3) 0.3097(2) 0.0813(9) Uani 1 1 d . . . O4 O 0.5333(7) 0.6683(4) -0.1636(3) 0.1160(14) Uani 1 1 d . . . Cl2 Cl 1.31415(14) 0.13600(8) 0.77855(8) 0.0705(3) Uani 1 1 d . . . Cl1 Cl 1.00992(12) 0.31722(9) 0.86630(7) 0.0621(2) Uani 1 1 d . . . Pd1 Pd 1.14719(3) 0.362368(18) 0.713414(16) 0.04096(9) Uani 1 1 d . . . S1 S 0.13729(16) 1.04811(10) 0.19433(8) 0.0711(3) Uani 1 1 d . . . S2 S 0.6570(4) 0.6770(3) -0.0919(2) 0.0676(6) Uani 0.50 1 d P A 1 S2A S 0.5494(3) 0.6428(2) -0.0447(2) 0.0765(5) Uani 0.50 1 d P A 2 H11A H 0.819(4) 1.063(3) 0.457(3) 0.036(8) Uiso 1 1 d . . . H10 H 1.421(4) 0.239(4) 0.592(3) 0.041(8) Uiso 1 1 d . . . H7 H 1.201(4) 0.694(4) 0.366(3) 0.043(8) Uiso 1 1 d . . . H1 H 0.859(4) 0.585(4) 0.757(3) 0.043(8) Uiso 1 1 d . . . H12B H 1.344(6) 0.612(4) 0.206(4) 0.066(12) Uiso 1 1 d . . . H4 H 1.002(5) 0.818(4) 0.424(3) 0.059(11) Uiso 1 1 d . . . H2 H 0.702(6) 0.818(5) 0.664(4) 0.083(14) Uiso 1 1 d . . . H11B H 0.691(7) 1.013(5) 0.404(4) 0.087(15) Uiso 1 1 d . . . H12A H 1.472(5) 0.639(4) 0.268(3) 0.062(11) Uiso 1 1 d . . . H9 H 1.519(5) 0.324(4) 0.432(3) 0.052(10) Uiso 1 1 d . . . H14A H -0.136(9) 1.146(7) 0.199(6) 0.12(2) Uiso 1 1 d . . . H13A H 0.175(7) 1.040(6) 0.027(5) 0.099(17) Uiso 1 1 d . . . H2O H 1.555(6) 0.433(4) 0.229(4) 0.054(13) Uiso 1 1 d . . . H16A H 0.614(6) 0.763(6) 0.044(3) 0.105(18) Uiso 1 1 d D . . H13B H 0.324(11) 0.913(8) 0.125(7) 0.16(3) Uiso 1 1 d . . . H13C H 0.137(6) 0.906(5) 0.122(4) 0.085(15) Uiso 1 1 d . . . H14C H -0.089(9) 1.024(8) 0.166(6) 0.13(2) Uiso 1 1 d . . . H14B H -0.124(16) 1.187(13) 0.086(11) 0.26(6) Uiso 1 1 d . . . H15A H 0.811(9) 0.519(7) 0.087(4) 0.14(3) Uiso 1 1 d D . . H16C H 0.612(10) 0.800(9) -0.082(5) 0.17(3) Uiso 1 1 d D . . H15B H 0.799(11) 0.441(6) 0.000(8) 0.20(4) Uiso 1 1 d D . . H15C H 0.701(3) 0.622(2) -0.0582(17) 0.003(7) Uiso 1 1 d D . . H16B H 0.439(5) 0.851(5) -0.061(5) 0.13(2) Uiso 1 1 d D . . H1O H 0.729(10) 1.095(14) 0.538(12) 0.37(9) 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 C1 0.0541(18) 0.0423(15) 0.0471(16) -0.0170(13) 0.0124(14) -0.0139(13) C2 0.0535(18) 0.0434(16) 0.0558(18) -0.0225(14) 0.0104(15) -0.0103(14) C3 0.0539(17) 0.0332(13) 0.0489(16) -0.0164(12) 0.0017(14) -0.0097(12) C11 0.077(2) 0.0368(16) 0.061(2) -0.0188(15) 0.0024(19) -0.0021(16) C4 0.0528(17) 0.0330(13) 0.0435(15) -0.0128(12) 0.0055(13) -0.0142(12) C5 0.0432(14) 0.0324(12) 0.0409(14) -0.0145(11) 0.0031(12) -0.0129(11) C6 0.0429(14) 0.0318(12) 0.0421(14) -0.0149(11) 0.0019(12) -0.0126(11) C7 0.0511(16) 0.0349(14) 0.0418(14) -0.0137(12) 0.0033(13) -0.0143(12) C8 0.0481(16) 0.0446(15) 0.0444(15) -0.0202(12) 0.0046(13) -0.0188(13) C12 0.0553(19) 0.062(2) 0.0484(17) -0.0250(15) 0.0116(15) -0.0237(16) C9 0.0503(18) 0.0428(16) 0.0563(18) -0.0262(14) 0.0089(15) -0.0090(14) C10 0.0509(17) 0.0331(14) 0.0522(16) -0.0171(13) 0.0038(14) -0.0080(12) C13 0.112(4) 0.069(3) 0.063(3) -0.022(2) 0.004(3) -0.022(3) C14 0.100(4) 0.088(4) 0.104(5) -0.004(4) 0.030(4) -0.015(3) C15 0.083(3) 0.079(3) 0.095(4) -0.044(3) 0.025(3) -0.012(3) C16 0.098(4) 0.083(3) 0.095(4) -0.055(3) -0.005(3) -0.007(3) N1 0.0439(12) 0.0344(11) 0.0401(12) -0.0129(9) 0.0037(10) -0.0126(10) N2 0.0465(13) 0.0289(10) 0.0432(12) -0.0128(9) 0.0015(10) -0.0095(9) O1 0.0772(18) 0.0491(14) 0.092(2) -0.0347(14) 0.0021(16) 0.0058(13) O2 0.0673(17) 0.088(2) 0.0778(19) -0.0477(18) 0.0289(15) -0.0281(16) O3 0.120(3) 0.0774(18) 0.0532(14) -0.0171(13) 0.0106(16) -0.0566(19) O4 0.165(4) 0.112(3) 0.087(2) -0.062(2) 0.005(3) -0.047(3) Cl2 0.0849(6) 0.0322(4) 0.0639(5) -0.0040(3) 0.0074(4) -0.0067(4) Cl1 0.0629(5) 0.0532(4) 0.0498(4) -0.0048(3) 0.0118(4) -0.0186(4) Pd1 0.04487(14) 0.03080(12) 0.03822(12) -0.00765(8) -0.00007(9) -0.01215(9) S1 0.1047(8) 0.0570(5) 0.0607(5) -0.0198(4) 0.0206(5) -0.0465(5) S2 0.1018(17) 0.0655(13) 0.0578(11) -0.0318(11) 0.0495(13) -0.0502(14) S2A 0.0825(14) 0.0730(12) 0.0815(13) -0.0367(11) 0.0185(12) -0.0334(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N1 1.347(4) . ? C1 C2 1.381(5) . ? C1 H1 0.95(4) . ? C2 C3 1.386(5) . ? C2 H2 0.98(5) . ? C3 C4 1.385(5) . ? C3 C11 1.511(4) . ? C11 O1 1.398(5) . ? C11 H11A 1.12(3) . ? C11 H11B 0.90(5) . ? C4 C5 1.383(4) . ? C4 H4 0.93(4) . ? C5 N1 1.354(4) . ? C5 C6 1.478(4) . ? C6 N2 1.362(3) . ? C6 C7 1.369(4) . ? C7 C8 1.394(4) . ? C7 H7 0.93(4) . ? C8 C9 1.387(5) . ? C8 C12 1.502(5) . ? C12 O2 1.410(5) . ? C12 H12B 0.96(4) . ? C12 H12A 0.98(4) . ? C9 C10 1.370(5) . ? C9 H9 0.79(4) . ? C10 N2 1.340(4) . ? C10 H10 0.94(3) . ? C13 S1 1.772(5) . ? C13 H13A 1.01(6) . ? C13 H13B 0.94(8) . ? C13 H13C 1.02(5) . ? C14 S1 1.771(8) . ? C14 H14A 0.92(7) . ? C14 H14C 1.00(7) . ? C14 H14B 0.86(13) . ? C15 S2 1.737(6) . ? C15 S2A 1.782(6) . ? C15 H15A 0.99(2) . ? C15 H15B 0.99(2) . ? C15 H15C 1.153(17) . ? C16 S2A 1.649(6) . ? C16 S2 1.741(6) . ? C16 H16A 0.98(2) . ? C16 H16C 0.99(2) . ? C16 H16B 0.98(2) . ? N1 Pd1 2.022(2) . ? N2 Pd1 2.018(3) . ? O1 H1O 1.01(2) . ? O2 H2O 0.72(4) . ? O3 S1 1.508(3) . ? O4 S2 1.468(5) . ? O4 S2A 1.472(4) . ? Cl2 Pd1 2.2869(8) . ? Cl1 Pd1 2.2967(9) . ? S2 H16C 1.39(9) . ? S2 H15C 0.595(17) . ? S2A H15C 1.24(3) . ? 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 N1 C1 C2 122.3(3) . . ? N1 C1 H1 118(2) . . ? C2 C1 H1 120(2) . . ? C1 C2 C3 119.7(3) . . ? C1 C2 H2 119(3) . . ? C3 C2 H2 121(3) . . ? C4 C3 C2 117.8(3) . . ? C4 C3 C11 120.0(3) . . ? C2 C3 C11 122.1(3) . . ? O1 C11 C3 113.8(3) . . ? O1 C11 H11A 90.6(16) . . ? C3 C11 H11A 117.8(17) . . ? O1 C11 H11B 113(3) . . ? C3 C11 H11B 109(3) . . ? H11A C11 H11B 112(4) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119(2) . . ? C3 C4 H4 121(2) . . ? N1 C5 C4 121.4(3) . . ? N1 C5 C6 115.0(2) . . ? C4 C5 C6 123.6(3) . . ? N2 C6 C7 121.6(3) . . ? N2 C6 C5 114.2(3) . . ? C7 C6 C5 124.2(2) . . ? C6 C7 C8 120.2(3) . . ? C6 C7 H7 117(2) . . ? C8 C7 H7 123(2) . . ? C9 C8 C7 117.4(3) . . ? C9 C8 C12 122.0(3) . . ? C7 C8 C12 120.5(3) . . ? O2 C12 C8 113.9(3) . . ? O2 C12 H12B 115(3) . . ? C8 C12 H12B 109(3) . . ? O2 C12 H12A 107(2) . . ? C8 C12 H12A 105(2) . . ? H12B C12 H12A 106(3) . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 119(3) . . ? C8 C9 H9 121(3) . . ? N2 C10 C9 122.4(3) . . ? N2 C10 H10 117(2) . . ? C9 C10 H10 121(2) . . ? S1 C13 H13A 105(3) . . ? S1 C13 H13B 109(5) . . ? H13A C13 H13B 113(6) . . ? S1 C13 H13C 101(3) . . ? H13A C13 H13C 115(4) . . ? H13B C13 H13C 111(6) . . ? S1 C14 H14A 105(5) . . ? S1 C14 H14C 94(4) . . ? H14A C14 H14C 109(6) . . ? S1 C14 H14B 116(9) . . ? H14A C14 H14B 103(9) . . ? H14C C14 H14B 129(9) . . ? S2 C15 S2A 39.84(17) . . ? S2 C15 H15A 117(4) . . ? S2A C15 H15A 118(4) . . ? S2 C15 H15B 116(6) . . ? S2A C15 H15B 116(6) . . ? H15A C15 H15B 123(7) . . ? S2 C15 H15C 4.6(14) . . ? S2A C15 H15C 43.9(13) . . ? H15A C15 H15C 118(4) . . ? H15B C15 H15C 113(6) . . ? S2A C16 S2 41.33(16) . . ? S2A C16 H16A 123(3) . . ? S2 C16 H16A 116(3) . . ? S2A C16 H16C 92(5) . . ? S2 C16 H16C 53(5) . . ? H16A C16 H16C 104(6) . . ? S2A C16 H16B 109(4) . . ? S2 C16 H16B 118(4) . . ? H16A C16 H16B 124(5) . . ? H16C C16 H16B 94(6) . . ? C1 N1 C5 118.5(2) . . ? C1 N1 Pd1 126.5(2) . . ? C5 N1 Pd1 115.02(19) . . ? C10 N2 C6 118.3(3) . . ? C10 N2 Pd1 126.3(2) . . ? C6 N2 Pd1 115.32(19) . . ? C11 O1 H1O 87(3) . . ? C12 O2 H2O 107(4) . . ? S2 O4 S2A 48.15(17) . . ? N2 Pd1 N1 80.45(10) . . ? N2 Pd1 Cl2 94.74(7) . . ? N1 Pd1 Cl2 175.10(8) . . ? N2 Pd1 Cl1 175.85(7) . . ? N1 Pd1 Cl1 95.50(8) . . ? Cl2 Pd1 Cl1 89.33(3) . . ? O3 S1 C14 106.4(3) . . ? O3 S1 C13 105.7(2) . . ? C14 S1 C13 98.0(4) . . ? O4 S2 C15 109.5(3) . . ? O4 S2 C16 109.2(3) . . ? C15 S2 C16 100.7(3) . . ? O4 S2 H16C 117(4) . . ? C15 S2 H16C 124(3) . . ? C16 S2 H16C 34.6(9) . . ? O4 S2 H15C 110(3) . . ? C15 S2 H15C 9(3) . . ? C16 S2 H15C 108(3) . . ? H16C S2 H15C 128(4) . . ? O4 S2A C16 114.1(3) . . ? O4 S2A C15 106.9(3) . . ? C16 S2A C15 102.5(3) . . ? O4 S2A H15C 80.6(11) . . ? C16 S2A H15C 86.8(12) . . ? C15 S2A H15C 40.0(8) . . ? 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 N1 C1 C2 C3 0.0(5) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C1 C2 C3 C11 177.5(4) . . . . ? C4 C3 C11 O1 -169.7(3) . . . . ? C2 C3 C11 O1 12.6(6) . . . . ? C2 C3 C4 C5 0.1(5) . . . . ? C11 C3 C4 C5 -177.8(3) . . . . ? C3 C4 C5 N1 0.5(5) . . . . ? C3 C4 C5 C6 178.1(3) . . . . ? N1 C5 C6 N2 -0.5(4) . . . . ? C4 C5 C6 N2 -178.3(3) . . . . ? N1 C5 C6 C7 178.1(3) . . . . ? C4 C5 C6 C7 0.3(5) . . . . ? N2 C6 C7 C8 -0.4(4) . . . . ? C5 C6 C7 C8 -178.8(3) . . . . ? C6 C7 C8 C9 0.1(5) . . . . ? C6 C7 C8 C12 178.6(3) . . . . ? C9 C8 C12 O2 -10.7(5) . . . . ? C7 C8 C12 O2 170.8(3) . . . . ? C7 C8 C9 C10 0.1(5) . . . . ? C12 C8 C9 C10 -178.4(3) . . . . ? C8 C9 C10 N2 -0.1(5) . . . . ? C2 C1 N1 C5 0.6(5) . . . . ? C2 C1 N1 Pd1 -178.6(3) . . . . ? C4 C5 N1 C1 -0.8(4) . . . . ? C6 C5 N1 C1 -178.7(3) . . . . ? C4 C5 N1 Pd1 178.5(2) . . . . ? C6 C5 N1 Pd1 0.6(3) . . . . ? C9 C10 N2 C6 -0.1(5) . . . . ? C9 C10 N2 Pd1 178.6(2) . . . . ? C7 C6 N2 C10 0.4(4) . . . . ? C5 C6 N2 C10 179.0(3) . . . . ? C7 C6 N2 Pd1 -178.5(2) . . . . ? C5 C6 N2 Pd1 0.1(3) . . . . ? C10 N2 Pd1 N1 -178.6(3) . . . . ? C6 N2 Pd1 N1 0.2(2) . . . . ? C10 N2 Pd1 Cl2 2.3(3) . . . . ? C6 N2 Pd1 Cl2 -178.89(19) . . . . ? C10 N2 Pd1 Cl1 -165.8(8) . . . . ? C6 N2 Pd1 Cl1 13.0(11) . . . . ? C1 N1 Pd1 N2 178.8(3) . . . . ? C5 N1 Pd1 N2 -0.5(2) . . . . ? C1 N1 Pd1 Cl2 -170.7(7) . . . . ? C5 N1 Pd1 Cl2 10.1(10) . . . . ? C1 N1 Pd1 Cl1 -0.3(3) . . . . ? C5 N1 Pd1 Cl1 -179.54(19) . . . . ? S2A O4 S2 C15 59.1(3) . . . . ? S2A O4 S2 C16 -50.2(3) . . . . ? S2A C15 S2 O4 -55.5(3) . . . . ? S2A C15 S2 C16 59.4(3) . . . . ? S2A C16 S2 O4 50.7(3) . . . . ? S2A C16 S2 C15 -64.5(3) . . . . ? S2 O4 S2A C16 57.1(3) . . . . ? S2 O4 S2A C15 -55.5(3) . . . . ? S2 C16 S2A O4 -53.0(3) . . . . ? S2 C16 S2A C15 62.3(3) . . . . ? S2 C15 S2A O4 54.1(3) . . . . ? S2 C15 S2A C16 -66.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 73.88 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.345 _refine_diff_density_min -0.712 _refine_diff_density_rms 0.087 #===END #=============================================================================== data_14 _database_code_depnum_ccdc_archive 'CCDC 828892' #TrackingRef '- 13_14.cif' #=============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cl2 N2 O4 Pd, C2 H6 O S' _chemical_formula_sum 'C14 H14 Cl2 N2 O5 Pd S' _chemical_formula_weight 499.63 _chemical_compound_source synthesis loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6738(3) _cell_length_b 10.4974(4) _cell_length_c 12.5545(4) _cell_angle_alpha 112.689(3) _cell_angle_beta 90.017(3) _cell_angle_gamma 108.646(3) _cell_volume 875.20(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7452 _cell_measurement_theta_min 3.8507 _cell_measurement_theta_max 73.7665 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.064 _exptl_crystal_size_mid 0.031 _exptl_crystal_size_min 0.018 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.896 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 12.748 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.71078 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CCD _diffrn_measurement_device_type 'Xcalibur, Onyx, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.2640 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9900 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 73.97 _reflns_number_total 3365 _reflns_number_gt 3059 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SIR2004(Burla, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2007)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0347P)^2^+0.5458P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3365 _refine_ls_number_parameters 292 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0640 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.85563(3) 0.27248(2) 0.416171(16) 0.04550(9) Uani 1 1 d . . . Cl1 Cl 0.89613(15) 0.12848(12) 0.23563(6) 0.0762(3) Uani 1 1 d . . . Cl2 Cl 0.66226(14) 0.34519(11) 0.33382(7) 0.0707(2) Uani 1 1 d . . . O1 O 1.5153(3) 0.1038(3) 0.66521(18) 0.0596(6) Uani 1 1 d D . . O2 O 1.4339(3) 0.2433(3) 0.82548(17) 0.0599(6) Uani 1 1 d . . . O3 O 0.6299(4) 0.6435(3) 0.95571(19) 0.0693(7) Uani 1 1 d D . . O4 O 0.8304(3) 0.5620(3) 1.01309(18) 0.0592(6) Uani 1 1 d . . . N2 N 0.8215(3) 0.3861(3) 0.58160(19) 0.0433(5) Uani 1 1 d . . . N1 N 1.0334(3) 0.2267(3) 0.50315(19) 0.0467(5) Uani 1 1 d . . . C1 C 1.1432(5) 0.1482(4) 0.4553(3) 0.0560(8) Uani 1 1 d . . . C2 C 1.2659(5) 0.1288(4) 0.5221(3) 0.0535(7) Uani 1 1 d . . . C3 C 1.2790(4) 0.1925(3) 0.6427(2) 0.0447(6) Uani 1 1 d . . . C4 C 1.1642(4) 0.2723(3) 0.6921(2) 0.0430(6) Uani 1 1 d . . . C5 C 1.0439(4) 0.2885(3) 0.6209(2) 0.0414(6) Uani 1 1 d . . . C6 C 0.9197(4) 0.3741(3) 0.6644(2) 0.0410(6) Uani 1 1 d . . . C7 C 0.8999(4) 0.4364(3) 0.7806(2) 0.0422(6) Uani 1 1 d . . . C8 C 0.7772(4) 0.5127(3) 0.8125(2) 0.0432(6) Uani 1 1 d . . . C9 C 0.6799(5) 0.5255(4) 0.7269(3) 0.0502(7) Uani 1 1 d . . . C10 C 0.7049(5) 0.4613(4) 0.6129(3) 0.0519(7) Uani 1 1 d . . . C11 C 1.4151(4) 0.1814(3) 0.7211(2) 0.0447(6) Uani 1 1 d . . . C12 C 0.7502(4) 0.5749(3) 0.9377(2) 0.0441(6) Uani 1 1 d . . . O5 O 0.7845(4) 0.1060(3) 0.7829(2) 0.0691(7) Uani 1 1 d . . . C13 C 0.7160(9) -0.0586(5) 0.9023(5) 0.0882(15) Uani 1 1 d . . . C14 C 0.7358(7) 0.2232(5) 1.0027(3) 0.0648(9) Uani 1 1 d . . . S1 S 0.6448(7) 0.0575(6) 0.8908(4) 0.0540(14) Uani 0.175(3) 1 d P A 1 S1A S 0.84381(12) 0.11182(10) 0.89983(7) 0.0475(3) Uani 0.825(3) 1 d P A 2 H1 H 1.129(5) 0.109(4) 0.369(4) 0.069(11) Uiso 1 1 d . . . H2 H 1.346(5) 0.073(4) 0.481(3) 0.068(11) Uiso 1 1 d . . . H4 H 1.171(5) 0.318(4) 0.774(3) 0.050(9) Uiso 1 1 d . . . H7 H 0.959(5) 0.426(4) 0.829(3) 0.047(9) Uiso 1 1 d . . . H9 H 0.603(6) 0.569(5) 0.740(4) 0.071(12) Uiso 1 1 d . . . H10 H 0.640(5) 0.464(4) 0.549(3) 0.065(10) Uiso 1 1 d . . . H13B H 0.589(10) -0.064(8) 0.866(6) 0.14(2) Uiso 1 1 d . . . H13A H 0.746(7) -0.128(6) 0.851(5) 0.101(17) Uiso 1 1 d . . . H13C H 0.719(7) -0.056(6) 0.978(5) 0.107(18) Uiso 1 1 d . . . H14A H 0.612(7) 0.176(5) 0.974(4) 0.093(16) Uiso 1 1 d . . . H14B H 0.763(7) 0.227(5) 1.076(5) 0.091(14) Uiso 1 1 d . . . H14C H 0.794(7) 0.319(6) 1.007(4) 0.102(17) Uiso 1 1 d . . . H1O H 1.606(6) 0.102(6) 0.722(4) 0.109(17) Uiso 1 1 d D . . H3O H 0.624(7) 0.678(5) 1.0400(19) 0.110(17) 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 Pd1 0.05172(13) 0.05782(14) 0.03145(11) 0.01534(9) 0.00350(8) 0.02819(10) Cl1 0.0989(7) 0.1082(7) 0.0322(3) 0.0149(4) 0.0075(4) 0.0665(6) Cl2 0.0843(6) 0.0978(6) 0.0461(4) 0.0253(4) -0.0021(4) 0.0567(5) O1 0.0712(14) 0.0835(15) 0.0410(10) 0.0178(10) 0.0142(10) 0.0576(13) O2 0.0724(14) 0.0840(15) 0.0354(10) 0.0142(10) 0.0093(9) 0.0551(13) O3 0.0940(18) 0.0984(18) 0.0464(12) 0.0271(12) 0.0225(12) 0.0755(16) O4 0.0737(14) 0.0767(15) 0.0399(10) 0.0182(10) 0.0086(10) 0.0489(12) N2 0.0474(12) 0.0526(13) 0.0350(11) 0.0154(9) 0.0041(9) 0.0269(11) N1 0.0539(14) 0.0592(14) 0.0307(10) 0.0136(10) 0.0076(9) 0.0303(12) C1 0.0671(19) 0.076(2) 0.0353(14) 0.0143(13) 0.0111(13) 0.0487(18) C2 0.0644(19) 0.0656(19) 0.0380(14) 0.0130(13) 0.0128(13) 0.0420(16) C3 0.0506(15) 0.0512(15) 0.0365(13) 0.0135(11) 0.0080(11) 0.0282(13) C4 0.0489(15) 0.0517(15) 0.0337(13) 0.0135(11) 0.0077(11) 0.0288(13) C5 0.0482(15) 0.0479(14) 0.0334(12) 0.0135(11) 0.0088(11) 0.0269(12) C6 0.0437(14) 0.0444(14) 0.0386(13) 0.0151(11) 0.0053(11) 0.0223(12) C7 0.0493(15) 0.0496(15) 0.0342(12) 0.0149(11) 0.0051(11) 0.0280(13) C8 0.0491(15) 0.0473(14) 0.0378(13) 0.0140(11) 0.0051(11) 0.0266(12) C9 0.0559(17) 0.0604(17) 0.0453(15) 0.0182(13) 0.0078(13) 0.0381(15) C10 0.0595(18) 0.0631(18) 0.0427(14) 0.0193(13) 0.0016(13) 0.0363(15) C11 0.0498(15) 0.0518(15) 0.0401(14) 0.0160(12) 0.0126(11) 0.0305(13) C12 0.0518(15) 0.0462(14) 0.0409(13) 0.0145(11) 0.0082(12) 0.0296(13) O5 0.0919(18) 0.0943(18) 0.0468(12) 0.0316(12) 0.0149(12) 0.0611(15) C13 0.125(4) 0.063(2) 0.080(3) 0.030(2) 0.038(3) 0.036(3) C14 0.081(3) 0.072(2) 0.0492(18) 0.0207(17) 0.0115(18) 0.041(2) S1 0.061(3) 0.066(3) 0.041(2) 0.0205(19) 0.0093(18) 0.032(2) S1A 0.0498(5) 0.0542(5) 0.0462(5) 0.0215(4) 0.0060(3) 0.0267(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N2 2.023(2) . ? Pd1 N1 2.027(2) . ? Pd1 Cl1 2.2752(8) . ? Pd1 Cl2 2.2771(8) . ? O1 C11 1.306(3) . ? O1 H1O 1.01(2) . ? O2 C11 1.201(3) . ? O3 C12 1.312(3) . ? O3 H3O 0.98(2) . ? O4 C12 1.202(4) . ? N2 C10 1.339(4) . ? N2 C6 1.351(3) . ? N1 C1 1.346(4) . ? N1 C5 1.356(3) . ? C1 C2 1.373(4) . ? C1 H1 0.99(4) . ? C2 C3 1.387(4) . ? C2 H2 0.99(4) . ? C3 C4 1.390(4) . ? C3 C11 1.497(4) . ? C4 C5 1.378(4) . ? C4 H4 0.94(4) . ? C5 C6 1.478(4) . ? C6 C7 1.380(4) . ? C7 C8 1.387(4) . ? C7 H7 0.81(4) . ? C8 C9 1.381(4) . ? C8 C12 1.494(4) . ? C9 C10 1.370(4) . ? C9 H9 0.84(4) . ? C10 H10 0.96(4) . ? O5 S1A 1.510(2) . ? O5 S1 1.852(5) . ? C13 S1 1.537(8) . ? C13 S1A 1.756(5) . ? C13 H13B 1.06(7) . ? C13 H13A 0.86(5) . ? C13 H13C 0.94(6) . ? C14 S1 1.681(6) . ? C14 S1A 1.782(4) . ? C14 H14A 0.92(5) . ? C14 H14B 0.92(5) . ? C14 H14C 0.94(5) . ? S1 H13B 1.11(7) . ? S1 H14A 1.38(5) . ? 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 N2 Pd1 N1 80.75(9) . . ? N2 Pd1 Cl1 174.66(7) . . ? N1 Pd1 Cl1 94.98(7) . . ? N2 Pd1 Cl2 94.41(7) . . ? N1 Pd1 Cl2 174.42(7) . . ? Cl1 Pd1 Cl2 90.01(3) . . ? C11 O1 H1O 110(3) . . ? C12 O3 H3O 105(3) . . ? C10 N2 C6 119.4(2) . . ? C10 N2 Pd1 125.86(19) . . ? C6 N2 Pd1 114.58(17) . . ? C1 N1 C5 119.1(2) . . ? C1 N1 Pd1 126.28(19) . . ? C5 N1 Pd1 114.56(18) . . ? N1 C1 C2 122.0(3) . . ? N1 C1 H1 114(2) . . ? C2 C1 H1 124(2) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H2 118(2) . . ? C3 C2 H2 123(2) . . ? C2 C3 C4 118.6(3) . . ? C2 C3 C11 122.3(2) . . ? C4 C3 C11 119.0(2) . . ? C5 C4 C3 119.5(2) . . ? C5 C4 H4 120(2) . . ? C3 C4 H4 121(2) . . ? N1 C5 C4 121.4(2) . . ? N1 C5 C6 114.8(2) . . ? C4 C5 C6 123.9(2) . . ? N2 C6 C7 121.1(2) . . ? N2 C6 C5 115.2(2) . . ? C7 C6 C5 123.6(2) . . ? C6 C7 C8 119.3(3) . . ? C6 C7 H7 119(2) . . ? C8 C7 H7 121(2) . . ? C9 C8 C7 118.8(3) . . ? C9 C8 C12 122.0(2) . . ? C7 C8 C12 119.2(2) . . ? C10 C9 C8 119.5(3) . . ? C10 C9 H9 117(3) . . ? C8 C9 H9 124(3) . . ? N2 C10 C9 121.9(3) . . ? N2 C10 H10 114(2) . . ? C9 C10 H10 124(2) . . ? O2 C11 O1 123.8(3) . . ? O2 C11 C3 122.5(2) . . ? O1 C11 C3 113.7(2) . . ? O4 C12 O3 124.1(3) . . ? O4 C12 C8 123.0(2) . . ? O3 C12 C8 113.0(2) . . ? S1A O5 S1 49.30(16) . . ? S1 C13 S1A 51.2(2) . . ? S1 C13 H13B 46(4) . . ? S1A C13 H13B 95(4) . . ? S1 C13 H13A 132(4) . . ? S1A C13 H13A 110(4) . . ? H13B C13 H13A 107(5) . . ? S1 C13 H13C 113(3) . . ? S1A C13 H13C 113(3) . . ? H13B C13 H13C 115(5) . . ? H13A C13 H13C 115(5) . . ? S1 C14 S1A 48.89(19) . . ? S1 C14 H14A 55(3) . . ? S1A C14 H14A 103(3) . . ? S1 C14 H14B 119(3) . . ? S1A C14 H14B 110(3) . . ? H14A C14 H14B 112(4) . . ? S1 C14 H14C 133(3) . . ? S1A C14 H14C 106(3) . . ? H14A C14 H14C 119(4) . . ? H14B C14 H14C 106(4) . . ? C13 S1 C14 112.9(4) . . ? C13 S1 O5 101.5(3) . . ? C14 S1 O5 96.4(3) . . ? C13 S1 H13B 43(4) . . ? C14 S1 H13B 145(4) . . ? O5 S1 H13B 112(4) . . ? C13 S1 H14A 131(2) . . ? C14 S1 H14A 33(2) . . ? O5 S1 H14A 113(2) . . ? H13B S1 H14A 134(4) . . ? O5 S1A C13 107.1(2) . . ? O5 S1A C14 106.08(16) . . ? C13 S1A C14 98.6(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 N1 Pd1 N2 C10 -177.9(3) . . . . ? Cl1 Pd1 N2 C10 -140.8(7) . . . . ? Cl2 Pd1 N2 C10 4.9(3) . . . . ? N1 Pd1 N2 C6 -2.2(2) . . . . ? Cl1 Pd1 N2 C6 34.9(9) . . . . ? Cl2 Pd1 N2 C6 -179.4(2) . . . . ? N2 Pd1 N1 C1 -176.9(3) . . . . ? Cl1 Pd1 N1 C1 6.3(3) . . . . ? Cl2 Pd1 N1 C1 -146.9(7) . . . . ? N2 Pd1 N1 C5 0.1(2) . . . . ? Cl1 Pd1 N1 C5 -176.7(2) . . . . ? Cl2 Pd1 N1 C5 30.1(9) . . . . ? C5 N1 C1 C2 0.0(5) . . . . ? Pd1 N1 C1 C2 176.9(3) . . . . ? N1 C1 C2 C3 -0.5(6) . . . . ? C1 C2 C3 C4 1.2(5) . . . . ? C1 C2 C3 C11 -177.4(3) . . . . ? C2 C3 C4 C5 -1.3(5) . . . . ? C11 C3 C4 C5 177.3(3) . . . . ? C1 N1 C5 C4 -0.1(5) . . . . ? Pd1 N1 C5 C4 -177.4(2) . . . . ? C1 N1 C5 C6 179.1(3) . . . . ? Pd1 N1 C5 C6 1.9(3) . . . . ? C3 C4 C5 N1 0.8(5) . . . . ? C3 C4 C5 C6 -178.4(3) . . . . ? C10 N2 C6 C7 0.9(4) . . . . ? Pd1 N2 C6 C7 -175.1(2) . . . . ? C10 N2 C6 C5 179.8(3) . . . . ? Pd1 N2 C6 C5 3.8(3) . . . . ? N1 C5 C6 N2 -3.8(4) . . . . ? C4 C5 C6 N2 175.4(3) . . . . ? N1 C5 C6 C7 175.1(3) . . . . ? C4 C5 C6 C7 -5.7(5) . . . . ? N2 C6 C7 C8 0.0(5) . . . . ? C5 C6 C7 C8 -178.9(3) . . . . ? C6 C7 C8 C9 -0.8(5) . . . . ? C6 C7 C8 C12 177.6(3) . . . . ? C7 C8 C9 C10 0.9(5) . . . . ? C12 C8 C9 C10 -177.5(3) . . . . ? C6 N2 C10 C9 -0.8(5) . . . . ? Pd1 N2 C10 C9 174.7(3) . . . . ? C8 C9 C10 N2 0.0(5) . . . . ? C2 C3 C11 O2 175.7(3) . . . . ? C4 C3 C11 O2 -2.8(5) . . . . ? C2 C3 C11 O1 -1.5(5) . . . . ? C4 C3 C11 O1 179.9(3) . . . . ? C9 C8 C12 O4 178.3(3) . . . . ? C7 C8 C12 O4 -0.1(5) . . . . ? C9 C8 C12 O3 -1.3(4) . . . . ? C7 C8 C12 O3 -179.7(3) . . . . ? S1A C13 S1 C14 -57.4(3) . . . . ? S1A C13 S1 O5 44.6(2) . . . . ? S1A C14 S1 C13 59.2(3) . . . . ? S1A C14 S1 O5 -46.18(16) . . . . ? S1A O5 S1 C13 -57.1(3) . . . . ? S1A O5 S1 C14 57.8(2) . . . . ? S1 O5 S1A C13 48.9(3) . . . . ? S1 O5 S1A C14 -55.7(3) . . . . ? S1 C13 S1A O5 -62.1(3) . . . . ? S1 C13 S1A C14 47.8(3) . . . . ? S1 C14 S1A O5 66.3(3) . . . . ? S1 C14 S1A C13 -44.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 73.97 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.549 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.058 #===END