# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Bruno Crociani' _publ_contact_author_email CROCIANI@STC.UNIROMA2.IT _publ_section_title ; Palladium complexes with a tridentate PNO ligand. Synthesis of ?1-allyl complexes and cross-coupling reactions promoted by boron compounds ; loop_ _publ_author_name 'Bruno Crociani' 'Simonetta Antonaroli' 'Marcello Burattini' 'Paola Paoli' 'Patrizia Rossi' # Attachment '1.cif.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 739327' #TrackingRef '1.cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 N O P Pd' _chemical_formula_weight 527.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8186(3) _cell_length_b 18.2721(5) _cell_length_c 12.9970(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.043(3) _cell_angle_gamma 90.00 _cell_volume 2280.43(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.905 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.636 _exptl_absorpt_correction_T_max 0.709 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16704 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0943 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 32.49 _reflns_number_total 7446 _reflns_number_gt 4554 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0214P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7446 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0655 _refine_ls_wR_factor_gt 0.0591 _refine_ls_goodness_of_fit_ref 0.829 _refine_ls_restrained_S_all 0.829 _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 0.686535(17) -0.035785(11) 0.276418(14) 0.02061(5) Uani 1 1 d . . . P1 P 0.72070(6) 0.07577(4) 0.22760(4) 0.01957(13) Uani 1 1 d . . . O1 O 0.65983(16) -0.13949(10) 0.33402(13) 0.0281(4) Uani 1 1 d . . . N1 N 0.51066(18) -0.01381(12) 0.33806(14) 0.0219(4) Uani 1 1 d . . . C1 C 0.5718(2) 0.13483(14) 0.23225(17) 0.0222(5) Uani 1 1 d . . . C2 C 0.5653(2) 0.20279(16) 0.18321(19) 0.0287(6) Uani 1 1 d . . . C3 C 0.4573(3) 0.25154(17) 0.1833(2) 0.0323(6) Uani 1 1 d . . . C4 C 0.3513(3) 0.23274(17) 0.2342(2) 0.0346(7) Uani 1 1 d . . . C5 C 0.3555(3) 0.16590(17) 0.2817(2) 0.0325(7) Uani 1 1 d . . . C6 C 0.4617(2) 0.11479(15) 0.28216(17) 0.0243(5) Uani 1 1 d . . . C7 C 0.4414(2) 0.04545(16) 0.33302(18) 0.0280(6) Uani 1 1 d . . . C8 C 0.4704(2) -0.07813(15) 0.38641(17) 0.0247(5) Uani 1 1 d . . . C9 C 0.3558(3) -0.08235(18) 0.4346(2) 0.0330(7) Uani 1 1 d . . . C10 C 0.3245(3) -0.1470(2) 0.4788(2) 0.0399(8) Uani 1 1 d . . . C11 C 0.4071(3) -0.2076(2) 0.4761(2) 0.0402(8) Uani 1 1 d . . . C12 C 0.5194(3) -0.20522(18) 0.4285(2) 0.0340(7) Uani 1 1 d . . . C13 C 0.5531(2) -0.14039(16) 0.38119(17) 0.0266(6) Uani 1 1 d . . . C14 C 0.8474(3) -0.07301(16) 0.2103(2) 0.0271(6) Uani 1 1 d . . . C15 C 0.7742(3) -0.11987(18) 0.1250(3) 0.0350(7) Uani 1 1 d . . . C16 C 0.7498(3) -0.1052(2) 0.0235(3) 0.0433(8) Uani 1 1 d . . . C17 C 0.7423(2) 0.08777(13) 0.09330(17) 0.0196(5) Uani 1 1 d . . . C18 C 0.6254(2) 0.07883(15) 0.01253(18) 0.0244(5) Uani 1 1 d . . . C19 C 0.6362(3) 0.08130(16) -0.09117(19) 0.0308(6) Uani 1 1 d . . . C20 C 0.7647(3) 0.09267(17) -0.1161(2) 0.0350(7) Uani 1 1 d . . . C21 C 0.8807(3) 0.10125(18) -0.0380(2) 0.0346(7) Uani 1 1 d . . . C22 C 0.8707(2) 0.09886(16) 0.06712(19) 0.0280(6) Uani 1 1 d . . . C23 C 0.8721(2) 0.11981(15) 0.31089(17) 0.0215(5) Uani 1 1 d . . . C24 C 0.9586(3) 0.07762(17) 0.3856(2) 0.0303(6) Uani 1 1 d . . . C25 C 1.0707(3) 0.10870(19) 0.4539(2) 0.0344(7) Uani 1 1 d . . . C26 C 1.0975(3) 0.18238(19) 0.4474(2) 0.0352(7) Uani 1 1 d . . . C27 C 1.0132(3) 0.22435(18) 0.3725(3) 0.0394(7) Uani 1 1 d . . . C28 C 0.9005(3) 0.19365(16) 0.3039(2) 0.0295(6) Uani 1 1 d . . . H2 H 0.637(2) 0.2144(14) 0.1458(17) 0.025(6) Uiso 1 1 d . . . H3 H 0.458(2) 0.2951(15) 0.1495(18) 0.025(7) Uiso 1 1 d . . . H4 H 0.277(2) 0.2654(14) 0.2343(16) 0.021(6) Uiso 1 1 d . . . H5 H 0.280(2) 0.1485(14) 0.3121(17) 0.025(6) Uiso 1 1 d . . . H7 H 0.360(2) 0.0479(14) 0.3659(17) 0.028(6) Uiso 1 1 d . . . H9 H 0.302(2) -0.0450(14) 0.4336(18) 0.021(7) Uiso 1 1 d . . . H10 H 0.250(2) -0.1466(15) 0.5049(18) 0.029(7) Uiso 1 1 d . . . H11 H 0.391(2) -0.2485(16) 0.5065(19) 0.037(8) Uiso 1 1 d . . . H12 H 0.572(2) -0.2447(16) 0.432(2) 0.036(8) Uiso 1 1 d . . . H14A H 0.9141(18) -0.0335(12) 0.1820(14) 0.005(5) Uiso 1 1 d . . . H14B H 0.894(3) -0.0973(17) 0.264(2) 0.040(8) Uiso 1 1 d . . . H15 H 0.744(3) -0.1606(17) 0.145(2) 0.047(9) Uiso 1 1 d . . . H16B H 0.705(3) -0.1348(19) -0.019(2) 0.056(11) Uiso 1 1 d . . . H16A H 0.780(3) -0.0622(18) -0.003(2) 0.048(10) Uiso 1 1 d . . . H18 H 0.538(2) 0.0750(13) 0.0286(16) 0.017(6) Uiso 1 1 d . . . H19 H 0.558(2) 0.0767(14) -0.1466(17) 0.020(6) Uiso 1 1 d . . . H20 H 0.771(2) 0.0912(16) -0.185(2) 0.038(7) Uiso 1 1 d . . . H21 H 0.963(2) 0.1081(16) -0.0542(19) 0.038(8) Uiso 1 1 d . . . H22 H 0.950(2) 0.1036(14) 0.1194(17) 0.021(6) Uiso 1 1 d . . . H24 H 0.940(3) 0.0330(15) 0.390(2) 0.028(7) Uiso 1 1 d . . . H25 H 1.125(2) 0.0854(15) 0.4982(18) 0.024(7) Uiso 1 1 d . . . H26 H 1.173(3) 0.2036(16) 0.492(2) 0.042(8) Uiso 1 1 d . . . H27 H 1.033(2) 0.2685(15) 0.3654(19) 0.021(7) Uiso 1 1 d . . . H28 H 0.840(2) 0.2243(15) 0.2517(18) 0.033(7) Uiso 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 0.01950(8) 0.01970(9) 0.02238(8) 0.00083(10) 0.00381(6) -0.00091(9) P1 0.0188(3) 0.0190(3) 0.0203(3) 0.0006(3) 0.0027(2) -0.0005(3) O1 0.0295(9) 0.0230(10) 0.0333(9) 0.0040(9) 0.0098(7) -0.0035(8) N1 0.0214(9) 0.0274(12) 0.0161(9) -0.0034(9) 0.0023(7) -0.0033(9) C1 0.0253(12) 0.0214(14) 0.0183(11) -0.0039(11) 0.0008(9) 0.0002(10) C2 0.0263(13) 0.0277(16) 0.0306(13) -0.0009(13) 0.0022(11) 0.0039(12) C3 0.0341(14) 0.0220(15) 0.0369(15) -0.0036(14) -0.0012(11) 0.0053(13) C4 0.0314(14) 0.0302(17) 0.0396(16) -0.0104(14) 0.0016(12) 0.0131(13) C5 0.0272(13) 0.0407(19) 0.0313(14) -0.0045(14) 0.0099(11) 0.0060(13) C6 0.0240(12) 0.0275(15) 0.0215(11) -0.0058(11) 0.0047(9) 0.0022(11) C7 0.0243(12) 0.0370(18) 0.0244(11) -0.0013(13) 0.0093(9) 0.0032(12) C8 0.0282(12) 0.0274(15) 0.0179(11) -0.0019(11) 0.0038(9) -0.0082(11) C9 0.0331(14) 0.0404(19) 0.0271(13) -0.0065(14) 0.0101(11) -0.0080(14) C10 0.0411(16) 0.053(2) 0.0294(14) -0.0041(15) 0.0170(13) -0.0207(16) C11 0.0497(17) 0.046(2) 0.0236(13) 0.0034(15) 0.0040(12) -0.0249(17) C12 0.0401(16) 0.0296(17) 0.0300(14) -0.0002(14) 0.0020(12) -0.0118(14) C13 0.0273(12) 0.0326(16) 0.0178(11) 0.0012(12) -0.0004(9) -0.0100(12) C14 0.0235(13) 0.0248(15) 0.0334(14) 0.0023(13) 0.0072(11) 0.0041(11) C15 0.0300(14) 0.0242(16) 0.055(2) -0.0100(15) 0.0180(13) -0.0016(13) C16 0.0324(16) 0.044(2) 0.052(2) -0.017(2) 0.0059(15) 0.0072(16) C17 0.0210(11) 0.0156(13) 0.0215(11) -0.0013(10) 0.0026(9) 0.0003(10) C18 0.0202(12) 0.0263(15) 0.0254(12) -0.0025(12) 0.0016(9) 0.0001(11) C19 0.0356(14) 0.0300(16) 0.0232(12) -0.0037(13) -0.0024(11) 0.0014(13) C20 0.0470(16) 0.0391(19) 0.0193(12) -0.0009(13) 0.0076(12) -0.0002(14) C21 0.0346(15) 0.0379(19) 0.0359(15) -0.0039(14) 0.0178(12) -0.0060(14) C22 0.0241(12) 0.0324(17) 0.0269(12) -0.0022(13) 0.0038(10) -0.0007(12) C23 0.0194(11) 0.0248(14) 0.0206(11) -0.0029(11) 0.0050(9) -0.0024(10) C24 0.0277(13) 0.0293(17) 0.0316(14) 0.0052(14) 0.0011(11) -0.0069(13) C25 0.0266(14) 0.047(2) 0.0255(13) 0.0042(15) -0.0026(11) -0.0005(14) C26 0.0236(13) 0.048(2) 0.0327(14) -0.0166(15) 0.0029(11) -0.0062(14) C27 0.0343(15) 0.0267(17) 0.057(2) -0.0125(17) 0.0087(14) -0.0066(14) C28 0.0273(13) 0.0253(15) 0.0344(14) -0.0026(13) 0.0031(11) 0.0003(12) _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 C14 2.065(2) . ? Pd1 O1 2.0741(17) . ? Pd1 N1 2.0887(17) . ? Pd1 P1 2.1814(7) . ? P1 C17 1.815(2) . ? P1 C1 1.829(2) . ? P1 C23 1.833(2) . ? O1 C13 1.320(3) . ? N1 C7 1.273(3) . ? N1 C8 1.427(3) . ? C1 C2 1.391(4) . ? C1 C6 1.419(3) . ? C2 C3 1.385(4) . ? C3 C4 1.387(4) . ? C4 C5 1.365(4) . ? C5 C6 1.399(3) . ? C6 C7 1.462(4) . ? C8 C9 1.400(3) . ? C8 C13 1.408(4) . ? C9 C10 1.376(4) . ? C10 C11 1.376(4) . ? C11 C12 1.373(4) . ? C12 C13 1.406(4) . ? C14 C15 1.465(4) . ? C15 C16 1.317(4) . ? C17 C22 1.388(3) . ? C17 C18 1.394(3) . ? C18 C19 1.374(3) . ? C19 C20 1.382(3) . ? C20 C21 1.367(4) . ? C21 C22 1.391(3) . ? C23 C24 1.384(4) . ? C23 C28 1.385(4) . ? C24 C25 1.383(4) . ? C25 C26 1.378(4) . ? C26 C27 1.373(4) . ? C27 C28 1.386(4) . ? 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 C14 Pd1 O1 90.84(9) . . ? C14 Pd1 N1 171.33(10) . . ? O1 Pd1 N1 81.97(7) . . ? C14 Pd1 P1 90.53(8) . . ? O1 Pd1 P1 175.83(5) . . ? N1 Pd1 P1 96.98(6) . . ? C17 P1 C1 102.41(10) . . ? C17 P1 C23 105.78(10) . . ? C1 P1 C23 106.09(11) . . ? C17 P1 Pd1 116.65(8) . . ? C1 P1 Pd1 111.67(8) . . ? C23 P1 Pd1 113.17(9) . . ? C13 O1 Pd1 110.58(16) . . ? C7 N1 C8 122.0(2) . . ? C7 N1 Pd1 128.26(17) . . ? C8 N1 Pd1 109.75(15) . . ? C2 C1 C6 118.2(2) . . ? C2 C1 P1 118.18(17) . . ? C6 C1 P1 123.6(2) . . ? C3 C2 C1 122.4(2) . . ? C2 C3 C4 119.5(3) . . ? C5 C4 C3 118.8(3) . . ? C4 C5 C6 123.5(2) . . ? C5 C6 C1 117.6(2) . . ? C5 C6 C7 114.1(2) . . ? C1 C6 C7 128.2(2) . . ? N1 C7 C6 129.7(2) . . ? C9 C8 C13 120.2(3) . . ? C9 C8 N1 124.4(3) . . ? C13 C8 N1 115.37(19) . . ? C10 C9 C8 120.3(3) . . ? C11 C10 C9 119.8(3) . . ? C12 C11 C10 121.2(3) . . ? C11 C12 C13 120.6(3) . . ? O1 C13 C12 119.8(3) . . ? O1 C13 C8 122.3(2) . . ? C12 C13 C8 117.9(2) . . ? C15 C14 Pd1 102.18(16) . . ? C16 C15 C14 126.7(3) . . ? C22 C17 C18 118.7(2) . . ? C22 C17 P1 123.21(17) . . ? C18 C17 P1 117.86(16) . . ? C19 C18 C17 121.0(2) . . ? C18 C19 C20 119.7(2) . . ? C21 C20 C19 120.3(2) . . ? C20 C21 C22 120.4(2) . . ? C17 C22 C21 120.0(2) . . ? C24 C23 C28 119.1(2) . . ? C24 C23 P1 118.3(2) . . ? C28 C23 P1 122.60(19) . . ? C25 C24 C23 120.7(3) . . ? C26 C25 C24 119.9(3) . . ? C27 C26 C25 119.6(3) . . ? C26 C27 C28 120.8(3) . . ? C23 C28 C27 119.8(3) . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 32.49 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 0.856 _refine_diff_density_min -0.612 _refine_diff_density_rms 0.098