Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Peter Styring' _publ_contact_author_address ; Department of Chemical & Process Engineering The University of Sheffield Mappin Street Sheffield S1 3JD UNITED KINGDOM ; _publ_contact_author_email P.STYRING@SHEFFIELD.AC.UK _publ_section_title ; Solid-supporting cross-coupling catalysts derived from homogeneouis nickel and palladium coordination complexes. ; loop_ _publ_author_name 'Peter Styring' 'Harry Adams' 'David H. Brown' 'Nam T.S. Phan' 'Sharon E. Spey' data_psty1m _database_code_depnum_ccdc_archive 'CCDC 203122' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 N2 Ni O5' _chemical_formula_weight 383.08 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' Ni Ni 0.3393 1.1124 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4282(16) _cell_length_b 9.916(2) _cell_length_c 12.270(3) _cell_angle_alpha 101.786(4) _cell_angle_beta 99.434(4) _cell_angle_gamma 95.531(4) _cell_volume 864.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2909 _cell_measurement_theta_min 4.827 _cell_measurement_theta_max 46.711 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 1.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6258 _exptl_absorpt_correction_T_max 0.7099 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3847 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 23.36 _reflns_number_total 2484 _reflns_number_gt 2254 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1181P)^2^+2.0085P] 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 2484 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1729 _refine_ls_wR_factor_gt 0.1678 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Ni1 Ni 0.13010(7) 0.41722(5) 0.32807(5) 0.0235(3) Uani 1 1 d . . . N1 N 0.2233(5) 0.5326(4) 0.4696(3) 0.0254(9) Uani 1 1 d . . . N2 N 0.0600(6) 0.5736(4) 0.2836(3) 0.0266(9) Uani 1 1 d . . . O1 O 0.1894(5) 0.2556(3) 0.3684(3) 0.0292(8) Uani 1 1 d . . . O2 O 0.0395(5) 0.3010(3) 0.1869(3) 0.0275(8) Uani 1 1 d . . . O3 O -0.3489(5) 0.1374(3) -0.1742(3) 0.0355(8) Uani 1 1 d . . . H3A H -0.3241 0.0623 -0.1621 0.053 Uiso 1 1 calc R . . C1 C 0.1888(7) 0.6775(5) 0.4792(4) 0.0299(11) Uani 1 1 d . . . H1A H 0.2955 0.7400 0.5244 0.036 Uiso 1 1 calc R . . H1B H 0.0841 0.6934 0.5158 0.036 Uiso 1 1 calc R . . C2 C 0.1502(7) 0.7040(5) 0.3614(4) 0.0329(11) Uani 1 1 d . . . H2A H 0.0707 0.7758 0.3590 0.039 Uiso 1 1 calc R . . H2B H 0.2643 0.7347 0.3396 0.039 Uiso 1 1 calc R . . C3 C -0.0524(7) 0.5784(5) 0.1926(4) 0.0283(11) Uani 1 1 d . . . H3B H -0.0842 0.6648 0.1848 0.034 Uiso 1 1 calc R . . C4 C -0.1319(6) 0.4606(5) 0.1029(4) 0.0258(10) Uani 1 1 d . . . C5 C -0.2588(7) 0.4775(5) 0.0101(4) 0.0318(11) Uani 1 1 d . . . H5A H -0.2955 0.5646 0.0106 0.038 Uiso 1 1 calc R . . C6 C -0.3301(7) 0.3711(5) -0.0805(4) 0.0323(11) Uani 1 1 d . . . H6A H -0.4145 0.3853 -0.1406 0.039 Uiso 1 1 calc R . . C7 C -0.2747(6) 0.2398(5) -0.0820(4) 0.0274(10) Uani 1 1 d . . . C8 C -0.1466(7) 0.2190(5) 0.0077(4) 0.0277(11) Uani 1 1 d . . . H8A H -0.1073 0.1323 0.0043 0.033 Uiso 1 1 calc R . . C9 C -0.0764(6) 0.3268(5) 0.1025(4) 0.0258(10) Uani 1 1 d . . . C10 C 0.2723(7) 0.2439(5) 0.4674(4) 0.0293(11) Uani 1 1 d . . . C11 C 0.3269(7) 0.3521(5) 0.5590(4) 0.0301(11) Uani 1 1 d . . . H11A H 0.3847 0.3324 0.6261 0.036 Uiso 1 1 calc R . . C12 C 0.3024(6) 0.4930(5) 0.5602(4) 0.0285(11) Uani 1 1 d . . . C13 C 0.3671(7) 0.5973(5) 0.6712(4) 0.0337(12) Uani 1 1 d . . . H13A H 0.3432 0.6880 0.6615 0.051 Uiso 1 1 calc R . . H13B H 0.4969 0.5985 0.6957 0.051 Uiso 1 1 calc R . . H13C H 0.3024 0.5719 0.7272 0.051 Uiso 1 1 calc R . . C14 C 0.3003(8) 0.0974(5) 0.4751(5) 0.0413(13) Uani 1 1 d . . . H14A H 0.2534 0.0356 0.4026 0.062 Uiso 1 1 calc R . . H14B H 0.2360 0.0705 0.5307 0.062 Uiso 1 1 calc R . . H14C H 0.4293 0.0928 0.4967 0.062 Uiso 1 1 calc R . . O1S O -0.2800(6) -0.1087(4) -0.1462(3) 0.0456(10) Uani 1 1 d . . . H1S H -0.2147 -0.1629 -0.1743 0.055 Uiso 1 1 calc R . . O2S O -0.7446(7) 0.1324(5) -0.2322(5) 0.0675(13) Uani 1 1 d . . . H2S H -0.6321 0.1367 -0.2189 0.081 Uiso 1 1 calc R . . C1S C -0.3644(9) -0.1654(6) -0.0690(5) 0.0460(14) Uani 1 1 d . . . H1S1 H -0.2719 -0.1772 -0.0085 0.069 Uiso 1 1 calc R . . H1S2 H -0.4341 -0.2540 -0.1068 0.069 Uiso 1 1 calc R . . H1S3 H -0.4452 -0.1039 -0.0387 0.069 Uiso 1 1 calc R . . C2S C -0.8229(13) -0.0030(6) -0.2456(6) 0.077(2) Uani 1 1 d . . . H2S1 H -0.7853 -0.0342 -0.1773 0.116 Uiso 1 1 calc R . . H2S2 H -0.7833 -0.0611 -0.3075 0.116 Uiso 1 1 calc R . . H2S3 H -0.9546 -0.0082 -0.2614 0.116 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0294(4) 0.0133(4) 0.0273(4) 0.0027(3) 0.0056(3) 0.0042(3) N1 0.029(2) 0.016(2) 0.030(2) 0.0018(17) 0.0095(17) 0.0001(16) N2 0.038(2) 0.0144(19) 0.030(2) 0.0052(16) 0.0108(18) 0.0047(17) O1 0.0382(19) 0.0183(17) 0.0307(19) 0.0054(14) 0.0035(15) 0.0072(14) O2 0.0372(18) 0.0166(16) 0.0272(18) 0.0031(13) 0.0009(14) 0.0089(14) O3 0.048(2) 0.0254(18) 0.0313(19) 0.0074(15) 0.0002(16) 0.0077(16) C1 0.032(3) 0.017(2) 0.038(3) 0.000(2) 0.009(2) 0.000(2) C2 0.044(3) 0.014(2) 0.038(3) 0.002(2) 0.008(2) 0.004(2) C3 0.037(3) 0.017(2) 0.038(3) 0.013(2) 0.014(2) 0.0087(19) C4 0.030(2) 0.020(2) 0.032(3) 0.009(2) 0.010(2) 0.0080(19) C5 0.039(3) 0.023(2) 0.039(3) 0.014(2) 0.011(2) 0.012(2) C6 0.034(3) 0.034(3) 0.034(3) 0.017(2) 0.004(2) 0.011(2) C7 0.030(2) 0.023(2) 0.031(3) 0.009(2) 0.007(2) 0.002(2) C8 0.035(3) 0.019(2) 0.031(3) 0.007(2) 0.007(2) 0.007(2) C9 0.029(2) 0.024(2) 0.028(3) 0.009(2) 0.011(2) 0.005(2) C10 0.032(3) 0.024(3) 0.034(3) 0.011(2) 0.006(2) 0.006(2) C11 0.032(3) 0.029(3) 0.030(3) 0.010(2) 0.003(2) 0.004(2) C12 0.025(2) 0.027(3) 0.034(3) 0.007(2) 0.008(2) -0.001(2) C13 0.038(3) 0.029(3) 0.031(3) 0.003(2) 0.004(2) -0.002(2) C14 0.056(3) 0.029(3) 0.039(3) 0.009(2) 0.000(3) 0.014(2) O1S 0.067(3) 0.0253(19) 0.055(2) 0.0115(18) 0.031(2) 0.0219(18) O2S 0.065(3) 0.051(3) 0.084(4) 0.018(3) 0.005(3) 0.007(2) C1S 0.063(4) 0.032(3) 0.045(3) 0.009(3) 0.013(3) 0.011(3) C2S 0.133(7) 0.030(3) 0.054(4) 0.004(3) 0.005(4) -0.026(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 Ni1 N2 1.839(4) . ? Ni1 O1 1.843(3) . ? Ni1 O2 1.853(3) . ? Ni1 N1 1.856(4) . ? N1 C12 1.320(7) . ? N1 C1 1.468(6) . ? N2 C3 1.292(7) . ? N2 C2 1.467(6) . ? O1 C10 1.302(6) . ? O2 C9 1.319(6) . ? O3 C7 1.355(6) . ? C1 C2 1.509(7) . ? C3 C4 1.433(7) . ? C4 C5 1.403(7) . ? C4 C9 1.427(7) . ? C5 C6 1.360(7) . ? C6 C7 1.400(7) . ? C7 C8 1.395(7) . ? C8 C9 1.397(7) . ? C10 C11 1.361(7) . ? C10 C14 1.506(7) . ? C11 C12 1.424(7) . ? C12 C13 1.507(7) . ? O1S C1S 1.396(7) . ? O2S C2S 1.377(7) . ? 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 Ni1 O1 177.14(15) . . ? N2 Ni1 O2 93.97(16) . . ? O1 Ni1 O2 83.83(14) . . ? N2 Ni1 N1 86.54(17) . . ? O1 Ni1 N1 95.68(16) . . ? O2 Ni1 N1 179.31(15) . . ? C12 N1 C1 119.6(4) . . ? C12 N1 Ni1 125.9(3) . . ? C1 N1 Ni1 114.4(3) . . ? C3 N2 C2 119.2(4) . . ? C3 N2 Ni1 127.1(3) . . ? C2 N2 Ni1 113.7(3) . . ? C10 O1 Ni1 126.6(3) . . ? C9 O2 Ni1 127.5(3) . . ? N1 C1 C2 108.2(4) . . ? N2 C2 C1 107.9(4) . . ? N2 C3 C4 125.0(4) . . ? C5 C4 C9 118.8(4) . . ? C5 C4 C3 119.9(4) . . ? C9 C4 C3 121.2(4) . . ? C6 C5 C4 122.4(4) . . ? C5 C6 C7 119.1(5) . . ? O3 C7 C8 122.7(4) . . ? O3 C7 C6 116.9(4) . . ? C8 C7 C6 120.4(4) . . ? C7 C8 C9 120.9(4) . . ? O2 C9 C8 118.8(4) . . ? O2 C9 C4 122.9(4) . . ? C8 C9 C4 118.4(4) . . ? O1 C10 C11 124.2(4) . . ? O1 C10 C14 114.4(4) . . ? C11 C10 C14 121.3(5) . . ? C10 C11 C12 125.1(5) . . ? N1 C12 C11 122.5(4) . . ? N1 C12 C13 120.4(4) . . ? C11 C12 C13 117.1(4) . . ? 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 N2 Ni1 N1 C12 178.3(4) . . . . ? O1 Ni1 N1 C12 0.1(4) . . . . ? O2 Ni1 N1 C12 -44(12) . . . . ? N2 Ni1 N1 C1 3.5(3) . . . . ? O1 Ni1 N1 C1 -174.7(3) . . . . ? O2 Ni1 N1 C1 142(12) . . . . ? O1 Ni1 N2 C3 -25(3) . . . . ? O2 Ni1 N2 C3 14.4(4) . . . . ? N1 Ni1 N2 C3 -166.0(4) . . . . ? O1 Ni1 N2 C2 157(3) . . . . ? O2 Ni1 N2 C2 -163.7(3) . . . . ? N1 Ni1 N2 C2 15.9(3) . . . . ? N2 Ni1 O1 C10 -142(3) . . . . ? O2 Ni1 O1 C10 178.7(4) . . . . ? N1 Ni1 O1 C10 -0.8(4) . . . . ? N2 Ni1 O2 C9 -15.9(4) . . . . ? O1 Ni1 O2 C9 162.3(4) . . . . ? N1 Ni1 O2 C9 -154(12) . . . . ? C12 N1 C1 C2 164.0(4) . . . . ? Ni1 N1 C1 C2 -20.9(5) . . . . ? C3 N2 C2 C1 151.2(4) . . . . ? Ni1 N2 C2 C1 -30.5(5) . . . . ? N1 C1 C2 N2 31.6(5) . . . . ? C2 N2 C3 C4 171.9(4) . . . . ? Ni1 N2 C3 C4 -6.1(7) . . . . ? N2 C3 C4 C5 177.3(5) . . . . ? N2 C3 C4 C9 -6.4(7) . . . . ? C9 C4 C5 C6 -0.4(7) . . . . ? C3 C4 C5 C6 176.0(4) . . . . ? C4 C5 C6 C7 -0.3(7) . . . . ? C5 C6 C7 O3 -179.7(4) . . . . ? C5 C6 C7 C8 -0.7(7) . . . . ? O3 C7 C8 C9 -178.6(4) . . . . ? C6 C7 C8 C9 2.5(7) . . . . ? Ni1 O2 C9 C8 -171.9(3) . . . . ? Ni1 O2 C9 C4 8.9(6) . . . . ? C7 C8 C9 O2 177.7(4) . . . . ? C7 C8 C9 C4 -3.1(7) . . . . ? C5 C4 C9 O2 -178.8(4) . . . . ? C3 C4 C9 O2 4.9(7) . . . . ? C5 C4 C9 C8 2.1(6) . . . . ? C3 C4 C9 C8 -174.3(4) . . . . ? Ni1 O1 C10 C11 1.0(7) . . . . ? Ni1 O1 C10 C14 179.4(3) . . . . ? O1 C10 C11 C12 -0.2(8) . . . . ? C14 C10 C11 C12 -178.6(5) . . . . ? C1 N1 C12 C11 175.0(4) . . . . ? Ni1 N1 C12 C11 0.4(6) . . . . ? C1 N1 C12 C13 -3.6(6) . . . . ? Ni1 N1 C12 C13 -178.1(3) . . . . ? C10 C11 C12 N1 -0.5(8) . . . . ? C10 C11 C12 C13 178.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 23.36 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.126 _refine_diff_density_min -0.885 _refine_diff_density_rms 0.124 data_psty3m _database_code_depnum_ccdc_archive 'CCDC 227121' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N2 O4 Pd' _chemical_formula_weight 398.73 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' 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 10.2935(10) _cell_length_b 10.4320(10) _cell_length_c 14.1939(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.984(2) _cell_angle_gamma 90.00 _cell_volume 1523.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7229 _cell_measurement_theta_min 4.840 _cell_measurement_theta_max 54.999 _exptl_crystal_description 'prismatic block' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 1.237 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.5939 _exptl_absorpt_correction_T_max 0.8863 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16923 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.56 _reflns_number_total 3513 _reflns_number_gt 2925 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0410P)^2^+0.6681P] 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 3513 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.507607(19) 0.113758(19) 0.904646(14) 0.01912(8) Uani 1 1 d . . . O1 O 0.4755(2) 0.26335(19) 0.98781(14) 0.0269(4) Uani 1 1 d . . . O2 O 0.32602(19) 0.14141(19) 0.85364(14) 0.0245(4) Uani 1 1 d . . . O3 O -0.0657(2) 0.0374(2) 0.69873(16) 0.0344(5) Uani 1 1 d . . . H3B H -0.1018 -0.0203 0.6664 0.052 Uiso 1 1 calc R . . N1 N 0.6882(2) 0.0873(2) 0.94694(17) 0.0246(5) Uani 1 1 d . . . N2 N 0.5376(2) -0.0381(2) 0.82826(17) 0.0226(5) Uani 1 1 d . . . C1 C 0.7424(3) -0.0353(3) 0.9152(2) 0.0325(7) Uani 1 1 d . . . H1A H 0.7300 -0.1017 0.9641 0.039 Uiso 1 1 calc R . . H1B H 0.8368 -0.0260 0.9047 0.039 Uiso 1 1 calc R . . C2 C 0.6749(3) -0.0750(3) 0.8252(2) 0.0329(7) Uani 1 1 d . . . H2A H 0.7166 -0.0330 0.7710 0.040 Uiso 1 1 calc R . . H2B H 0.6821 -0.1690 0.8170 0.040 Uiso 1 1 calc R . . C3 C 0.4501(3) -0.0972(3) 0.7794(2) 0.0247(6) Uani 1 1 d . . . H3A H 0.4760 -0.1742 0.7492 0.030 Uiso 1 1 calc R . . C4 C 0.3173(3) -0.0586(3) 0.76578(19) 0.0227(6) Uani 1 1 d . . . C5 C 0.2372(3) -0.1410(3) 0.7106(2) 0.0287(7) Uani 1 1 d . . . H5A H 0.2727 -0.2192 0.6883 0.034 Uiso 1 1 calc R . . C6 C 0.1115(3) -0.1125(3) 0.6881(2) 0.0288(7) Uani 1 1 d . . . H6A H 0.0603 -0.1705 0.6516 0.035 Uiso 1 1 calc R . . C7 C 0.0584(3) 0.0026(3) 0.7193(2) 0.0260(6) Uani 1 1 d . . . C8 C 0.1337(3) 0.0869(3) 0.7733(2) 0.0250(6) Uani 1 1 d . . . H8A H 0.0968 0.1657 0.7931 0.030 Uiso 1 1 calc R . . C9 C 0.2626(3) 0.0581(3) 0.79908(19) 0.0217(6) Uani 1 1 d . . . C10 C 0.5674(3) 0.3112(3) 1.0411(2) 0.0270(6) Uani 1 1 d . . . C11 C 0.6943(3) 0.2729(3) 1.0468(2) 0.0288(7) Uani 1 1 d . . . H11A H 0.7510 0.3260 1.0830 0.035 Uiso 1 1 calc R . . C12 C 0.7509(3) 0.1642(3) 1.0053(2) 0.0258(6) Uani 1 1 d . . . C13 C 0.8913(3) 0.1374(3) 1.0316(2) 0.0363(8) Uani 1 1 d . . . H13A H 0.9204 0.0601 0.9988 0.054 Uiso 1 1 calc R . . H13B H 0.8993 0.1243 1.0998 0.054 Uiso 1 1 calc R . . H13C H 0.9452 0.2104 1.0132 0.054 Uiso 1 1 calc R . . C14 C 0.5236(3) 0.4170(3) 1.1050(2) 0.0345(7) Uani 1 1 d . . . H14A H 0.4311 0.4343 1.0934 0.052 Uiso 1 1 calc R . . H14B H 0.5740 0.4947 1.0925 0.052 Uiso 1 1 calc R . . H14C H 0.5372 0.3911 1.1708 0.052 Uiso 1 1 calc R . . O1S O 0.8104(3) 0.8601(2) 0.59545(16) 0.0417(6) Uani 1 1 d . . . H1S H 0.7673 0.7927 0.6032 0.062 Uiso 1 1 calc R . . C1S C 0.8245(3) 0.8832(3) 0.4973(2) 0.0359(7) Uani 1 1 d . . . H1S1 H 0.7892 0.9679 0.4815 0.054 Uiso 1 1 calc R . . H1S2 H 0.7771 0.8174 0.4613 0.054 Uiso 1 1 calc R . . H1S3 H 0.9167 0.8801 0.4815 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.01741(12) 0.01824(12) 0.02167(12) 0.00059(8) -0.00062(8) 0.00152(8) O1 0.0262(11) 0.0253(10) 0.0290(11) -0.0079(9) -0.0053(8) 0.0024(8) O2 0.0206(10) 0.0225(10) 0.0302(11) -0.0082(8) -0.0053(8) 0.0034(8) O3 0.0214(11) 0.0404(13) 0.0411(13) -0.0097(10) -0.0091(9) -0.0018(9) N1 0.0204(12) 0.0262(13) 0.0273(13) 0.0041(10) 0.0014(10) 0.0016(10) N2 0.0196(12) 0.0204(12) 0.0279(13) 0.0012(10) 0.0032(10) 0.0022(9) C1 0.0231(16) 0.0372(18) 0.0373(18) 0.0002(14) -0.0001(13) 0.0082(13) C2 0.0257(16) 0.0348(17) 0.0383(18) -0.0056(14) 0.0024(13) 0.0070(13) C3 0.0348(17) 0.0169(13) 0.0227(14) 0.0009(11) 0.0060(12) 0.0057(12) C4 0.0277(15) 0.0206(13) 0.0199(14) 0.0008(11) 0.0017(11) -0.0013(12) C5 0.0356(17) 0.0205(14) 0.0300(16) -0.0037(12) 0.0032(13) -0.0012(12) C6 0.0322(17) 0.0257(15) 0.0285(16) -0.0030(12) -0.0023(13) -0.0089(13) C7 0.0226(15) 0.0309(15) 0.0244(15) 0.0015(12) 0.0015(11) -0.0053(12) C8 0.0220(15) 0.0231(14) 0.0299(15) -0.0058(12) -0.0003(12) 0.0023(11) C9 0.0237(14) 0.0218(14) 0.0196(14) 0.0006(11) 0.0008(11) -0.0032(11) C10 0.0326(17) 0.0232(15) 0.0249(15) 0.0028(11) -0.0038(12) -0.0024(12) C11 0.0284(16) 0.0305(16) 0.0274(16) 0.0014(12) -0.0048(12) -0.0081(13) C12 0.0226(15) 0.0322(15) 0.0225(14) 0.0093(12) -0.0033(11) -0.0026(12) C13 0.0237(16) 0.046(2) 0.0391(19) 0.0020(15) -0.0037(14) -0.0006(14) C14 0.0393(19) 0.0329(17) 0.0310(17) -0.0081(13) -0.0046(14) 0.0002(14) O1S 0.0476(15) 0.0422(14) 0.0348(13) 0.0082(10) -0.0117(11) -0.0252(11) C1S 0.0350(18) 0.0348(18) 0.0377(18) 0.0033(14) -0.0022(14) -0.0067(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 Pd1 N2 1.948(2) . ? Pd1 N1 1.963(2) . ? Pd1 O1 1.9877(19) . ? Pd1 O2 2.014(2) . ? O1 C10 1.300(3) . ? O2 C9 1.328(3) . ? O3 C7 1.355(4) . ? N1 C12 1.315(4) . ? N1 C1 1.469(4) . ? N2 C3 1.285(4) . ? N2 C2 1.465(4) . ? C1 C2 1.503(4) . ? C3 C4 1.436(4) . ? C4 C5 1.418(4) . ? C4 C9 1.426(4) . ? C5 C6 1.360(5) . ? C6 C7 1.395(4) . ? C7 C8 1.393(4) . ? C8 C9 1.403(4) . ? C10 C11 1.366(4) . ? C10 C14 1.504(4) . ? C11 C12 1.409(4) . ? C12 C13 1.512(4) . ? O1S C1S 1.424(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 N2 Pd1 N1 84.11(10) . . ? N2 Pd1 O1 177.28(9) . . ? N1 Pd1 O1 95.44(9) . . ? N2 Pd1 O2 94.10(9) . . ? N1 Pd1 O2 176.72(9) . . ? O1 Pd1 O2 86.48(8) . . ? C10 O1 Pd1 121.33(19) . . ? C9 O2 Pd1 124.05(17) . . ? C12 N1 C1 122.6(3) . . ? C12 N1 Pd1 124.0(2) . . ? C1 N1 Pd1 113.05(19) . . ? C3 N2 C2 121.7(2) . . ? C3 N2 Pd1 125.1(2) . . ? C2 N2 Pd1 113.11(19) . . ? N1 C1 C2 109.1(2) . . ? N2 C2 C1 109.5(3) . . ? N2 C3 C4 126.5(3) . . ? C5 C4 C9 118.1(3) . . ? C5 C4 C3 116.6(3) . . ? C9 C4 C3 125.2(3) . . ? C6 C5 C4 122.6(3) . . ? C5 C6 C7 119.4(3) . . ? O3 C7 C8 117.6(3) . . ? O3 C7 C6 122.4(3) . . ? C8 C7 C6 120.1(3) . . ? C7 C8 C9 121.5(3) . . ? O2 C9 C8 117.7(3) . . ? O2 C9 C4 124.0(3) . . ? C8 C9 C4 118.3(3) . . ? O1 C10 C11 127.4(3) . . ? O1 C10 C14 114.2(3) . . ? C11 C10 C14 118.3(3) . . ? C10 C11 C12 127.8(3) . . ? N1 C12 C11 123.5(3) . . ? N1 C12 C13 120.0(3) . . ? C11 C12 C13 116.5(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 N2 Pd1 O1 C10 83.8(19) . . . . ? N1 Pd1 O1 C10 3.5(2) . . . . ? O2 Pd1 O1 C10 -173.8(2) . . . . ? N2 Pd1 O2 C9 9.2(2) . . . . ? N1 Pd1 O2 C9 66.0(16) . . . . ? O1 Pd1 O2 C9 -168.2(2) . . . . ? N2 Pd1 N1 C12 177.1(2) . . . . ? O1 Pd1 N1 C12 -5.6(2) . . . . ? O2 Pd1 N1 C12 120.0(15) . . . . ? N2 Pd1 N1 C1 -9.3(2) . . . . ? O1 Pd1 N1 C1 168.0(2) . . . . ? O2 Pd1 N1 C1 -66.4(16) . . . . ? N1 Pd1 N2 C3 172.8(2) . . . . ? O1 Pd1 N2 C3 92.2(19) . . . . ? O2 Pd1 N2 C3 -9.9(2) . . . . ? N1 Pd1 N2 C2 -11.8(2) . . . . ? O1 Pd1 N2 C2 -92.4(19) . . . . ? O2 Pd1 N2 C2 165.5(2) . . . . ? C12 N1 C1 C2 -158.9(3) . . . . ? Pd1 N1 C1 C2 27.4(3) . . . . ? C3 N2 C2 C1 -154.8(3) . . . . ? Pd1 N2 C2 C1 29.6(3) . . . . ? N1 C1 C2 N2 -36.1(4) . . . . ? C2 N2 C3 C4 -170.1(3) . . . . ? Pd1 N2 C3 C4 4.9(4) . . . . ? N2 C3 C4 C5 -178.5(3) . . . . ? N2 C3 C4 C9 5.0(5) . . . . ? C9 C4 C5 C6 0.3(4) . . . . ? C3 C4 C5 C6 -176.5(3) . . . . ? C4 C5 C6 C7 0.8(5) . . . . ? C5 C6 C7 O3 179.3(3) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? O3 C7 C8 C9 179.1(3) . . . . ? C6 C7 C8 C9 -1.2(4) . . . . ? Pd1 O2 C9 C8 176.4(2) . . . . ? Pd1 O2 C9 C4 -3.3(4) . . . . ? C7 C8 C9 O2 -177.5(3) . . . . ? C7 C8 C9 C4 2.2(4) . . . . ? C5 C4 C9 O2 177.9(3) . . . . ? C3 C4 C9 O2 -5.6(4) . . . . ? C5 C4 C9 C8 -1.7(4) . . . . ? C3 C4 C9 C8 174.7(3) . . . . ? Pd1 O1 C10 C11 2.3(4) . . . . ? Pd1 O1 C10 C14 -175.3(2) . . . . ? O1 C10 C11 C12 -8.3(5) . . . . ? C14 C10 C11 C12 169.2(3) . . . . ? C1 N1 C12 C11 -170.9(3) . . . . ? Pd1 N1 C12 C11 2.1(4) . . . . ? C1 N1 C12 C13 8.7(4) . . . . ? Pd1 N1 C12 C13 -178.3(2) . . . . ? C10 C11 C12 N1 5.7(5) . . . . ? C10 C11 C12 C13 -173.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.196 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.094