# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Armando J. L. Pombeiro' _publ_contact_author_email POMBEIRO@IST.UTL.PT _publ_section_title ; PdII-Promoted [2+3] Cycloaddition of Pyrrolin N-oxide to Organonitriles. Application of fused bicyclic (?4-1,2,4-oxadiazoline)-PdII Complexes in the Microwave-Assisted Suzuki-Miyaura Cross-Coupling in Aqueous Medium ; loop_ _publ_author_name 'Armando J. L. Pombeiro' 'Adilia Charmier' 'M Fatima C Guedes da Silva' 'Maximilian N Kopylovich' ; J.Lasri ; 'Suman Mukhopadhyay' # Attachment 'combinedcifs.cif' data_compound3b _database_code_depnum_ccdc_archive 'CCDC 698356' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H32 Cl2 N4 O2 Pd' _chemical_formula_sum 'C18 H32 Cl2 N4 O2 Pd' _chemical_formula_weight 513.78 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.6844(14) _cell_length_b 6.6806(8) _cell_length_c 14.2895(18) _cell_angle_alpha 90.00 _cell_angle_beta 91.092(3) _cell_angle_gamma 90.00 _cell_volume 1115.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3765 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.07 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 1.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7215 _exptl_absorpt_correction_T_max 0.8802 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 5742 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 25.34 _reflns_number_total 1890 _reflns_number_gt 1701 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0236P)^2^+0.8814P] 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 1890 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0553 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.00110(17) 0.3166(3) 0.85259(15) 0.0189(5) Uani 1 1 d . . . C2 C 0.09029(19) 0.4455(4) 0.89672(16) 0.0226(5) Uani 1 1 d . . . H2A H 0.1166 0.3839 0.9564 0.027 Uiso 1 1 calc R . . H2B H 0.0567 0.5777 0.9113 0.027 Uiso 1 1 calc R . . C3 C 0.1921(2) 0.4744(4) 0.8338(2) 0.0413(7) Uani 1 1 d . . . H3A H 0.2488 0.5604 0.8653 0.062 Uiso 1 1 calc R . . H3B H 0.1667 0.5373 0.7751 0.062 Uiso 1 1 calc R . . H3C H 0.2267 0.3441 0.8204 0.062 Uiso 1 1 calc R . . C4 C -0.0907(2) 0.1421(4) 0.64939(16) 0.0270(5) Uani 1 1 d . . . C5 C -0.0339(3) 0.2961(5) 0.58721(19) 0.0512(8) Uani 1 1 d . . . H5A H -0.0893 0.4008 0.5703 0.077 Uiso 1 1 calc R . . H5B H -0.0071 0.2308 0.5303 0.077 Uiso 1 1 calc R . . H5C H 0.0314 0.3561 0.6210 0.077 Uiso 1 1 calc R . . C6 C -0.2005(2) 0.0662(5) 0.60203(18) 0.0369(6) Uani 1 1 d . . . H6A H -0.2367 -0.0330 0.6424 0.055 Uiso 1 1 calc R . . H6B H -0.1822 0.0042 0.5420 0.055 Uiso 1 1 calc R . . H6C H -0.2530 0.1786 0.5913 0.055 Uiso 1 1 calc R . . C7 C -0.0135(2) -0.0304(4) 0.68166(19) 0.0367(7) Uani 1 1 d . . . H7A H -0.0062 -0.1324 0.6318 0.044 Uiso 1 1 calc R . . H7B H 0.0637 0.0185 0.6999 0.044 Uiso 1 1 calc R . . C8 C -0.0753(2) -0.1149(4) 0.76548(17) 0.0319(6) Uani 1 1 d . . . H8A H -0.0220 -0.1880 0.8079 0.038 Uiso 1 1 calc R . . H8B H -0.1381 -0.2058 0.7456 0.038 Uiso 1 1 calc R . . C9 C -0.12187(19) 0.0728(4) 0.81233(15) 0.0210(5) Uani 1 1 d . . . H9 H -0.1980 0.0464 0.8406 0.025 Uiso 1 1 calc R . . N1 N -0.04015(15) 0.1523(3) 0.88253(12) 0.0182(4) Uani 1 1 d . . . N2 N -0.13041(15) 0.2354(3) 0.73921(12) 0.0197(4) Uani 1 1 d . . . O1 O -0.04127(13) 0.3809(2) 0.77044(10) 0.0228(4) Uani 1 1 d . . . Cl1 Cl -0.18536(5) 0.04086(9) 1.04773(4) 0.02568(14) Uani 1 1 d . . . Pd1 Pd 0.0000 0.0000 1.0000 0.01634(9) Uani 1 2 d S . . 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 0.0206(10) 0.0182(13) 0.0179(11) 0.0003(9) 0.0001(8) 0.0031(9) C2 0.0261(11) 0.0164(12) 0.0253(12) 0.0002(10) -0.0037(9) -0.0034(9) C3 0.0324(14) 0.0400(18) 0.0520(18) -0.0146(13) 0.0111(13) -0.0135(12) C4 0.0318(12) 0.0310(15) 0.0181(11) -0.0018(10) -0.0001(9) -0.0019(10) C5 0.071(2) 0.061(2) 0.0220(14) 0.0005(13) 0.0135(13) -0.0199(17) C6 0.0451(15) 0.0401(16) 0.0251(13) -0.0024(12) -0.0141(11) 0.0006(13) C7 0.0311(13) 0.0443(18) 0.0344(14) -0.0165(12) -0.0040(11) 0.0117(12) C8 0.0448(15) 0.0191(15) 0.0311(14) -0.0032(10) -0.0180(11) 0.0041(11) C9 0.0243(11) 0.0198(13) 0.0186(11) 0.0034(9) -0.0052(9) -0.0028(9) N1 0.0214(9) 0.0167(10) 0.0165(9) 0.0012(8) -0.0035(7) -0.0022(8) N2 0.0217(9) 0.0199(11) 0.0175(9) 0.0008(8) -0.0035(7) -0.0028(8) O1 0.0300(8) 0.0172(9) 0.0210(8) 0.0048(6) -0.0071(7) -0.0040(7) Cl1 0.0249(3) 0.0255(3) 0.0267(3) 0.0013(2) 0.0004(2) 0.0008(2) Pd1 0.02140(13) 0.01366(16) 0.01378(13) 0.00218(9) -0.00415(9) -0.00206(9) _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 C1 N1 1.276(3) . ? C1 O1 1.336(3) . ? C1 C2 1.483(3) . ? C2 C3 1.517(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 N2 1.508(3) . ? C4 C5 1.520(3) . ? C4 C6 1.526(3) . ? C4 C7 1.529(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.519(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.526(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N1 1.471(3) . ? C9 N2 1.509(3) . ? C9 H9 1.0000 . ? N1 Pd1 2.0108(18) . ? N2 O1 1.487(2) . ? Cl1 Pd1 2.2993(6) . ? Pd1 N1 2.0108(18) 3_557 ? Pd1 Cl1 2.2993(6) 3_557 ? 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 O1 115.78(19) . . ? N1 C1 C2 128.6(2) . . ? O1 C1 C2 115.64(19) . . ? C1 C2 C3 112.0(2) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 C5 111.2(2) . . ? N2 C4 C6 104.18(18) . . ? C5 C4 C6 109.8(2) . . ? N2 C4 C7 104.14(19) . . ? C5 C4 C7 115.1(2) . . ? C6 C4 C7 111.7(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C4 103.34(19) . . ? C8 C7 H7A 111.1 . . ? C4 C7 H7A 111.1 . . ? C8 C7 H7B 111.1 . . ? C4 C7 H7B 111.1 . . ? H7A C7 H7B 109.1 . . ? C7 C8 C9 102.7(2) . . ? C7 C8 H8A 111.2 . . ? C9 C8 H8A 111.2 . . ? C7 C8 H8B 111.2 . . ? C9 C8 H8B 111.2 . . ? H8A C8 H8B 109.1 . . ? N1 C9 N2 104.22(17) . . ? N1 C9 C8 111.33(18) . . ? N2 C9 C8 107.87(18) . . ? N1 C9 H9 111.1 . . ? N2 C9 H9 111.1 . . ? C8 C9 H9 111.1 . . ? C1 N1 C9 109.06(18) . . ? C1 N1 Pd1 129.17(15) . . ? C9 N1 Pd1 121.64(14) . . ? O1 N2 C4 107.48(15) . . ? O1 N2 C9 103.06(15) . . ? C4 N2 C9 105.92(17) . . ? C1 O1 N2 107.42(15) . . ? N1 Pd1 N1 180.0 3_557 . ? N1 Pd1 Cl1 91.06(5) 3_557 . ? N1 Pd1 Cl1 88.94(5) . . ? N1 Pd1 Cl1 88.94(5) 3_557 3_557 ? N1 Pd1 Cl1 91.06(5) . 3_557 ? Cl1 Pd1 Cl1 180.0 . 3_557 ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.339 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.059 data_compound3d _database_code_depnum_ccdc_archive 'CCDC 698357' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H30 Br2 Cl2 N4 O2 Pd' _chemical_formula_sum 'C26 H30 Br2 Cl2 N4 O2 Pd' _chemical_formula_weight 767.66 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.7889(6) _cell_length_b 11.2477(3) _cell_length_c 13.3097(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.300(2) _cell_angle_gamma 90.00 _cell_volume 2944.58(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5695 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 23.81 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.732 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 3.556 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3958 _exptl_absorpt_correction_T_max 0.5084 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 19219 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2691 _reflns_number_gt 2156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0325P)^2^+6.8702P] 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 2691 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0684 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 C1 C 0.13034(17) 0.2470(3) 0.3849(3) 0.0382(8) Uani 1 1 d . . . C2 C 0.17286(17) 0.2926(3) 0.3100(3) 0.0400(8) Uani 1 1 d . . . C3 C 0.16238(18) 0.2566(3) 0.2102(3) 0.0485(9) Uani 1 1 d . . . H3 H 0.1287 0.2012 0.1902 0.058 Uiso 1 1 calc R . . C4 C 0.20187(19) 0.3028(3) 0.1399(3) 0.0512(10) Uani 1 1 d . . . H4 H 0.1945 0.2795 0.0725 0.061 Uiso 1 1 calc R . . C5 C 0.25175(18) 0.3829(3) 0.1707(3) 0.0483(9) Uani 1 1 d . . . C6 C 0.2638(2) 0.4183(4) 0.2697(3) 0.0558(10) Uani 1 1 d . . . H6 H 0.2981 0.4728 0.2895 0.067 Uiso 1 1 calc R . . C7 C 0.22440(18) 0.3718(3) 0.3396(3) 0.0497(9) Uani 1 1 d . . . H7 H 0.2327 0.3941 0.4071 0.060 Uiso 1 1 calc R . . C8 C 0.05061(18) 0.1711(3) 0.4712(3) 0.0451(9) Uani 1 1 d . . . H8 H 0.0466 0.0843 0.4722 0.054 Uiso 1 1 calc R . . C9 C -0.01272(19) 0.2287(4) 0.5055(3) 0.0538(10) Uani 1 1 d . . . H9A H -0.0313 0.2879 0.4572 0.065 Uiso 1 1 calc R . . H9B H -0.0474 0.1696 0.5138 0.065 Uiso 1 1 calc R . . C10 C 0.0123(2) 0.2861(4) 0.6064(3) 0.0539(10) Uani 1 1 d . . . H10A H -0.0148 0.3554 0.6184 0.065 Uiso 1 1 calc R . . H10B H 0.0100 0.2303 0.6615 0.065 Uiso 1 1 calc R . . C11 C 0.08552(19) 0.3211(3) 0.5971(3) 0.0452(9) Uani 1 1 d . . . C12 C 0.0894(2) 0.4351(3) 0.5361(3) 0.0529(10) Uani 1 1 d . . . H12A H 0.0648 0.4248 0.4705 0.079 Uiso 1 1 calc R . . H12B H 0.1361 0.4529 0.5290 0.079 Uiso 1 1 calc R . . H12C H 0.0698 0.4994 0.5705 0.079 Uiso 1 1 calc R . . C13 C 0.1280(2) 0.3330(4) 0.6983(3) 0.0678(12) Uani 1 1 d . . . H13A H 0.1256 0.2605 0.7358 0.102 Uiso 1 1 calc R . . H13B H 0.1109 0.3975 0.7355 0.102 Uiso 1 1 calc R . . H13C H 0.1744 0.3487 0.6878 0.102 Uiso 1 1 calc R . . N1 N 0.06924(14) 0.2117(2) 0.3727(2) 0.0386(7) Uani 1 1 d . . . N2 N 0.10776(15) 0.2111(3) 0.5450(2) 0.0452(7) Uani 1 1 d . . . Cl1 Cl 0.0000 0.41519(10) 0.2500 0.0488(3) Uani 1 2 d S . . Br1 Br 0.30620(3) 0.44617(5) 0.07488(4) 0.07380(18) Uani 1 1 d . . . Cl3 Cl 0.0000 0.00991(14) 0.2500 0.1302(11) Uani 1 2 d S . . Pd1 Pd 0.0000 0.21236(3) 0.2500 0.03742(13) Uani 1 2 d S . . O1 O 0.16093(12) 0.2413(2) 0.48071(18) 0.0453(6) 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 C1 0.0350(19) 0.0364(17) 0.042(2) -0.0023(15) -0.0032(15) 0.0064(14) C2 0.0338(18) 0.0394(18) 0.046(2) -0.0024(16) -0.0006(15) 0.0076(15) C3 0.039(2) 0.051(2) 0.056(2) -0.0103(18) 0.0020(17) -0.0046(16) C4 0.046(2) 0.061(2) 0.045(2) -0.0063(19) 0.0018(17) -0.0007(19) C5 0.040(2) 0.044(2) 0.061(3) 0.0045(18) 0.0036(18) 0.0053(16) C6 0.048(2) 0.052(2) 0.065(3) -0.004(2) -0.004(2) -0.0128(18) C7 0.045(2) 0.055(2) 0.047(2) -0.0048(18) -0.0047(18) -0.0053(18) C8 0.045(2) 0.0352(18) 0.054(2) 0.0063(16) -0.0013(18) 0.0029(15) C9 0.044(2) 0.055(2) 0.063(3) 0.003(2) 0.0085(19) -0.0010(18) C10 0.056(2) 0.055(2) 0.052(2) 0.0097(19) 0.0111(19) 0.0097(19) C11 0.048(2) 0.045(2) 0.042(2) -0.0004(16) 0.0036(17) 0.0116(16) C12 0.054(2) 0.044(2) 0.061(3) -0.0024(18) 0.006(2) 0.0058(17) C13 0.066(3) 0.082(3) 0.053(3) -0.007(2) -0.007(2) 0.021(2) N1 0.0375(16) 0.0314(14) 0.0459(17) -0.0005(13) 0.0002(13) 0.0040(12) N2 0.0465(17) 0.0436(17) 0.0452(18) 0.0047(14) 0.0033(14) 0.0091(14) Cl1 0.0662(9) 0.0288(6) 0.0493(8) 0.000 -0.0029(6) 0.000 Br1 0.0700(3) 0.0783(3) 0.0751(3) 0.0118(2) 0.0173(3) -0.0148(2) Cl3 0.178(2) 0.0285(8) 0.158(2) 0.000 -0.0995(18) 0.000 Pd1 0.0334(2) 0.02808(19) 0.0490(2) 0.000 -0.00333(16) 0.000 O1 0.0375(13) 0.0524(14) 0.0445(15) 0.0010(12) -0.0031(11) 0.0105(11) _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 C1 N1 1.266(4) . ? C1 O1 1.352(4) . ? C1 C2 1.466(5) . ? C2 C7 1.378(5) . ? C2 C3 1.382(5) . ? C3 C4 1.384(5) . ? C3 H3 0.9300 . ? C4 C5 1.366(5) . ? C4 H4 0.9300 . ? C5 C6 1.372(5) . ? C5 Br1 1.897(4) . ? C6 C7 1.381(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N1 1.473(5) . ? C8 N2 1.484(5) . ? C8 C9 1.525(5) . ? C8 H8 0.9800 . ? C9 C10 1.522(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.519(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.507(4) . ? C11 C13 1.514(5) . ? C11 C12 1.523(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? N1 Pd1 2.014(3) . ? N2 O1 1.467(4) . ? Cl1 Pd1 2.2814(12) . ? Cl3 Pd1 2.2770(16) . ? Pd1 N1 2.014(3) 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 N1 C1 O1 115.4(3) . . ? N1 C1 C2 129.4(3) . . ? O1 C1 C2 115.3(3) . . ? C7 C2 C3 119.4(3) . . ? C7 C2 C1 119.6(3) . . ? C3 C2 C1 120.9(3) . . ? C2 C3 C4 120.2(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.2(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.6(4) . . ? C4 C5 Br1 119.4(3) . . ? C6 C5 Br1 119.0(3) . . ? C5 C6 C7 119.0(4) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C2 C7 C6 120.5(4) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? N1 C8 N2 104.4(3) . . ? N1 C8 C9 115.4(3) . . ? N2 C8 C9 105.4(3) . . ? N1 C8 H8 110.5 . . ? N2 C8 H8 110.5 . . ? C9 C8 H8 110.5 . . ? C10 C9 C8 104.2(3) . . ? C10 C9 H9A 110.9 . . ? C8 C9 H9A 110.9 . . ? C10 C9 H9B 110.9 . . ? C8 C9 H9B 110.9 . . ? H9A C9 H9B 108.9 . . ? C11 C10 C9 105.0(3) . . ? C11 C10 H10A 110.7 . . ? C9 C10 H10A 110.7 . . ? C11 C10 H10B 110.7 . . ? C9 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? N2 C11 C13 108.7(3) . . ? N2 C11 C10 98.8(3) . . ? C13 C11 C10 113.0(3) . . ? N2 C11 C12 114.3(3) . . ? C13 C11 C12 110.1(4) . . ? C10 C11 C12 111.5(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C1 N1 C8 108.2(3) . . ? C1 N1 Pd1 131.1(3) . . ? C8 N1 Pd1 120.6(2) . . ? O1 N2 C8 103.2(3) . . ? O1 N2 C11 110.0(3) . . ? C8 N2 C11 108.2(3) . . ? N1 Pd1 N1 179.61(15) 2 . ? N1 Pd1 Cl3 89.80(7) 2 . ? N1 Pd1 Cl3 89.80(7) . . ? N1 Pd1 Cl1 90.20(7) 2 . ? N1 Pd1 Cl1 90.20(7) . . ? Cl3 Pd1 Cl1 180.0 . . ? C1 O1 N2 106.6(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.707 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.069 # Attachment 'compound5-F.cif' data_jl216b _database_code_depnum_ccdc_archive 'CCDC 698358' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H30 Cl2 F2 N4 O2 Pd' _chemical_formula_sum 'C26 H30 Cl2 F2 N4 O2 Pd' _chemical_formula_weight 645.84 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3090(14) _cell_length_b 9.4080(18) _cell_length_c 10.818(2) _cell_angle_alpha 105.666(11) _cell_angle_beta 105.464(12) _cell_angle_gamma 102.764(10) _cell_volume 655.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4974 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.24 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.959 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7490 _exptl_absorpt_correction_T_max 0.8936 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 7226 _diffrn_reflns_av_R_equivalents 0.1167 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2308 _reflns_number_gt 2073 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0200P)^2^+0.1455P] 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 2308 _refine_ls_number_parameters 169 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0675 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.052 _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 C1 C 0.6844(4) 0.1681(3) 0.9021(3) 0.0197(6) Uani 1 1 d . . . C2 C 0.8069(5) 0.0566(3) 0.8951(4) 0.0316(8) Uani 1 1 d . . . H2A H 0.8113 0.0195 0.8025 0.047 Uiso 1 1 calc R . . H2B H 0.7450 -0.0321 0.9174 0.047 Uiso 1 1 calc R . . H2C H 0.9432 0.1107 0.9608 0.047 Uiso 1 1 calc R . . C3 C 0.6735(5) 0.2298(3) 1.0432(3) 0.0276(7) Uani 1 1 d . . . H3A H 0.5933 0.3006 1.0438 0.041 Uiso 1 1 calc R . . H3B H 0.8088 0.2859 1.1098 0.041 Uiso 1 1 calc R . . H3C H 0.6114 0.1429 1.0675 0.041 Uiso 1 1 calc R . . C4 C 0.4787(5) 0.0951(3) 0.7888(3) 0.0224(6) Uani 1 1 d . . . H4A H 0.3804 0.1426 0.8152 0.027 Uiso 1 1 calc R . . H4B H 0.4288 -0.0185 0.7678 0.027 Uiso 1 1 calc R . . C5 C 0.5166(4) 0.1310(3) 0.6662(3) 0.0212(6) Uani 1 1 d . . . H5A H 0.5560 0.0488 0.6108 0.025 Uiso 1 1 calc R . . H5B H 0.3983 0.1454 0.6069 0.025 Uiso 1 1 calc R . . C6 C 0.6853(4) 0.2794(3) 0.7387(3) 0.0171(6) Uani 1 1 d . . . C7 C 0.6710(5) 0.3682(3) 0.5425(3) 0.0207(6) Uani 1 1 d . . . C8 C 0.7504(4) 0.5078(3) 0.5076(3) 0.0195(6) Uani 1 1 d . . . C9 C 0.8655(5) 0.6527(3) 0.6040(3) 0.0264(7) Uani 1 1 d . . . H9 H 0.8876 0.6701 0.6982 0.032 Uiso 1 1 calc R . . C10 C 0.9496(5) 0.7735(4) 0.5647(3) 0.0297(7) Uani 1 1 d . . . H10 H 1.0310 0.8730 0.6301 0.036 Uiso 1 1 calc R . . C11 C 0.9088(5) 0.7417(4) 0.4258(4) 0.0287(8) Uani 1 1 d . . . C12 C 0.7885(5) 0.6043(4) 0.3283(3) 0.0297(8) Uani 1 1 d . . . H12 H 0.7598 0.5899 0.2340 0.036 Uiso 1 1 calc R . . C13 C 0.7076(5) 0.4846(3) 0.3690(3) 0.0260(7) Uani 1 1 d . . . H13 H 0.6230 0.3868 0.3023 0.031 Uiso 1 1 calc R . . N1 N 0.7786(4) 0.3035(2) 0.8645(2) 0.0159(5) Uani 1 1 d . . . N2 N 0.7400(4) 0.3878(3) 0.6798(2) 0.0210(5) Uani 1 1 d D . . O1 O 0.5612(4) 0.2458(2) 0.4563(2) 0.0307(5) Uani 1 1 d . . . Cl1 Cl 1.23377(11) 0.37238(8) 1.02772(7) 0.02533(18) Uani 1 1 d . . . F1 F 0.9951(3) 0.8581(2) 0.3866(2) 0.0439(6) Uani 1 1 d . . . Pd1 Pd 1.0000 0.5000 1.0000 0.01405(11) Uani 1 2 d S . . H2 H 0.7566 0.4784 0.7359 0.017 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 0.0184(17) 0.0138(15) 0.0241(16) 0.0086(12) 0.0064(12) -0.0015(12) C2 0.027(2) 0.0216(17) 0.050(2) 0.0208(15) 0.0100(15) 0.0087(15) C3 0.0268(19) 0.0269(18) 0.0207(16) 0.0091(13) 0.0061(13) -0.0059(14) C4 0.0207(18) 0.0175(15) 0.0215(16) 0.0068(12) 0.0037(12) -0.0039(13) C5 0.0235(18) 0.0176(15) 0.0183(15) 0.0053(12) 0.0041(12) 0.0037(13) C6 0.0182(17) 0.0152(14) 0.0169(15) 0.0057(11) 0.0055(12) 0.0039(12) C7 0.0228(18) 0.0232(17) 0.0178(15) 0.0076(13) 0.0079(12) 0.0095(14) C8 0.0188(17) 0.0232(16) 0.0201(15) 0.0107(12) 0.0069(12) 0.0094(13) C9 0.029(2) 0.0260(17) 0.0217(16) 0.0117(13) 0.0028(13) 0.0075(14) C10 0.027(2) 0.0218(17) 0.0356(19) 0.0132(14) 0.0034(14) 0.0032(14) C11 0.032(2) 0.0292(18) 0.042(2) 0.0252(16) 0.0215(16) 0.0168(16) C12 0.046(2) 0.0289(18) 0.0249(17) 0.0149(14) 0.0191(16) 0.0178(16) C13 0.035(2) 0.0238(17) 0.0215(16) 0.0078(13) 0.0125(14) 0.0111(15) N1 0.0161(14) 0.0137(12) 0.0175(12) 0.0066(9) 0.0058(10) 0.0028(10) N2 0.0270(16) 0.0171(13) 0.0161(12) 0.0064(10) 0.0051(10) 0.0039(11) O1 0.0439(15) 0.0204(12) 0.0173(11) 0.0044(9) 0.0049(10) -0.0001(10) Cl1 0.0201(4) 0.0212(4) 0.0299(4) 0.0052(3) 0.0038(3) 0.0080(3) F1 0.0569(15) 0.0327(12) 0.0602(14) 0.0310(11) 0.0344(12) 0.0129(10) Pd1 0.01395(19) 0.01353(17) 0.01225(17) 0.00458(11) 0.00294(12) 0.00161(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 C1 C3 1.510(4) . ? C1 N1 1.518(3) . ? C1 C2 1.522(4) . ? C1 C4 1.530(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.532(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.489(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.281(3) . ? C6 N2 1.382(3) . ? C7 O1 1.205(4) . ? C7 N2 1.381(3) . ? C7 C8 1.501(4) . ? C8 C9 1.383(4) . ? C8 C13 1.391(4) . ? C9 C10 1.393(4) . ? C9 H9 0.9500 . ? C10 C11 1.384(4) . ? C10 H10 0.9500 . ? C11 C12 1.350(5) . ? C11 F1 1.365(3) . ? C12 C13 1.387(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? N1 Pd1 2.033(2) . ? N2 H2 0.864 . ? Cl1 Pd1 2.2975(8) . ? Pd1 N1 2.033(2) 2_767 ? Pd1 Cl1 2.2975(8) 2_767 ? 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 C3 C1 N1 109.1(2) . . ? C3 C1 C2 111.7(2) . . ? N1 C1 C2 109.2(2) . . ? C3 C1 C4 113.2(2) . . ? N1 C1 C4 101.8(2) . . ? C2 C1 C4 111.3(3) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 C5 103.7(2) . . ? C1 C4 H4A 111.0 . . ? C5 C4 H4A 111.0 . . ? C1 C4 H4B 111.0 . . ? C5 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C6 C5 C4 100.1(2) . . ? C6 C5 H5A 111.7 . . ? C4 C5 H5A 111.7 . . ? C6 C5 H5B 111.7 . . ? C4 C5 H5B 111.7 . . ? H5A C5 H5B 109.5 . . ? N1 C6 N2 120.6(3) . . ? N1 C6 C5 114.9(2) . . ? N2 C6 C5 124.5(2) . . ? O1 C7 N2 122.3(2) . . ? O1 C7 C8 122.4(2) . . ? N2 C7 C8 115.3(3) . . ? C9 C8 C13 119.7(2) . . ? C9 C8 C7 123.9(2) . . ? C13 C8 C7 116.3(3) . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 116.8(3) . . ? C11 C10 H10 121.6 . . ? C9 C10 H10 121.6 . . ? C12 C11 F1 118.8(3) . . ? C12 C11 C10 123.9(2) . . ? F1 C11 C10 117.2(3) . . ? C11 C12 C13 118.5(3) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C12 C13 C8 120.0(3) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? C6 N1 C1 109.2(2) . . ? C6 N1 Pd1 126.11(17) . . ? C1 N1 Pd1 124.38(17) . . ? C7 N2 C6 126.5(2) . . ? C7 N2 H2 115.7 . . ? C6 N2 H2 107.8 . . ? N1 Pd1 N1 180.0 2_767 . ? N1 Pd1 Cl1 87.00(7) 2_767 . ? N1 Pd1 Cl1 93.00(7) . . ? N1 Pd1 Cl1 93.00(7) 2_767 2_767 ? N1 Pd1 Cl1 87.00(7) . 2_767 ? Cl1 Pd1 Cl1 180.0 . 2_767 ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 1.085 _refine_diff_density_min -1.657 _refine_diff_density_rms 0.134