# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Bianchini, C.' 'Lee, H.M.' 'Mantovani, Giuseppe' 'Meli, Andrea' 'Oberhauser, Werner' _publ_contact_author_name 'Dr C Bianchini' _publ_contact_author_address ; Inst per lo Studio della Stereochimica ed Energetica dei Composti di Coordinazio ISSECC-CNR Via j. Nardi 39 50132 Firenze ITALY ; _publ_contact_author_email ' bianchin@fi.cnr.it ' _publ_section_title ; Bis-alkoxycarbonylation of styrene by pyridinimine palladium catalysts ; data_1a _database_code_CSD 178390 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H14 F6 N2 O4 Pd' _chemical_formula_weight 542.71 _chemical_melting_point ? _chemical_compound_source ? 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' 'F' 'F' 0.0171 0.0103 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.383(3) _cell_length_b 9.774(2) _cell_length_c 11.585(2) _cell_angle_alpha 85.90(2) _cell_angle_beta 89.74(2) _cell_angle_gamma 70.79(2) _cell_volume 1000.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_method ? _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 1.008 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3700 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3508 _reflns_number_observed 3162 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1209P)^2^+3.1050P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3508 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_obs 0.0636 _refine_ls_wR_factor_all 0.1832 _refine_ls_wR_factor_obs 0.1755 _refine_ls_goodness_of_fit_all 1.055 _refine_ls_goodness_of_fit_obs 1.068 _refine_ls_restrained_S_all 1.055 _refine_ls_restrained_S_obs 1.068 _refine_ls_shift/esd_max 0.171 _refine_ls_shift/esd_mean 0.031 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Pd1 Pd 0.12824(5) 0.26200(5) 0.15748(4) 0.0444(2) Uani 1 d . . N1 N 0.0557(6) 0.1596(6) 0.2875(5) 0.0472(12) Uani 1 d . . N2 N -0.0391(6) 0.2243(6) 0.0751(5) 0.0478(12) Uani 1 d . . O1 O 0.3019(6) 0.2779(5) 0.2486(5) 0.0565(12) Uani 1 d . . O3 O 0.1879(6) 0.3700(5) 0.0230(4) 0.0556(11) Uani 1 d . . O2 O 0.1817(7) 0.5127(7) 0.2673(5) 0.0724(15) Uiso 1 d . . O4 O 0.3247(9) 0.1678(9) -0.0522(7) 0.096(2) Uiso 1 d . . C1 C -0.0487(9) 0.1126(8) 0.2600(6) 0.0556(17) Uani 1 d . . H1 H -0.0872 0.0595 0.3139 0.078(12) Uiso 1 calc R . C2 C -0.1074(8) 0.1444(7) 0.1407(6) 0.0525(16) Uani 1 d . . C3 C -0.2191(10) 0.1021(9) 0.0974(7) 0.071(2) Uani 1 d . . H3 H -0.2626 0.0453 0.1435 0.078(12) Uiso 1 calc R . C4 C -0.2677(11) 0.1446(9) -0.0167(7) 0.070(2) Uani 1 d . . H4 H -0.3439 0.1167 -0.0483 0.078(12) Uiso 1 calc R . C5 C -0.2020(10) 0.2271(9) -0.0805(7) 0.067(2) Uani 1 d . . H5 H -0.2332 0.2567 -0.1570 0.078(12) Uiso 1 calc R . C6 C -0.0881(8) 0.2682(8) -0.0330(6) 0.0537(16) Uani 1 d . . H6 H -0.0456 0.3272 -0.0775 0.078(12) Uiso 1 calc R . C7 C 0.3258(12) -0.0760(10) 0.3489(8) 0.082(3) Uani 1 d . . H7A H 0.3435 -0.0258 0.2789 0.099(14) Uiso 1 calc R . H7B H 0.2635 -0.1330 0.3319 0.099(14) Uiso 1 calc R . H7C H 0.4205 -0.1386 0.3818 0.099(14) Uiso 1 calc R . C8 C -0.1058(11) 0.3652(12) 0.4466(8) 0.088(3) Uani 1 d . . H8A H -0.1346 0.4295 0.5079 0.099(14) Uiso 1 calc R . H8B H -0.1842 0.3250 0.4328 0.099(14) Uiso 1 calc R . H8C H -0.0903 0.4182 0.3774 0.099(14) Uiso 1 calc R . C9 C 0.2874(8) 0.4027(7) 0.2824(6) 0.0500(15) Uani 1 d . . C10 C 0.4243(10) 0.4044(8) 0.3495(7) 0.0594(18) Uani 1 d . . C11 C 0.2815(8) 0.2970(7) -0.0473(6) 0.0538(16) Uani 1 d . . C12 C 0.3322(9) 0.3867(9) -0.1353(7) 0.0615(18) Uani 1 d . . C2,1 C 0.2471(5) 0.0332(4) 0.4341(3) 0.0527(16) Uani 1 d G . C3,1 C 0.3104(4) 0.0251(4) 0.5437(4) 0.0578(17) Uani 1 d G . H3,1 H 0.4008 -0.0477 0.5646 0.069 Uiso 1 calc R . C4,1 C 0.2385(5) 0.1258(5) 0.6220(3) 0.0610(19) Uani 1 d G . H4,1 H 0.2808 0.1203 0.6953 0.073 Uiso 1 calc R . C5,1 C 0.1033(5) 0.2346(5) 0.5907(3) 0.0604(18) Uani 1 d G . H5,1 H 0.0552 0.3019 0.6432 0.072 Uiso 1 calc R . C6,1 C 0.0400(4) 0.2427(4) 0.4811(4) 0.0551(16) Uani 1 d G . C1,1 C 0.1119(5) 0.1421(5) 0.4028(3) 0.0443(13) Uani 1 d G . F1 F 0.4255(8) 0.5357(8) 0.3608(6) 0.1044(19) Uiso 1 d . . F2 F 0.4241(7) 0.3432(7) 0.4563(6) 0.0983(17) Uiso 1 d . . F3 F 0.5544(8) 0.3292(8) 0.3055(6) 0.107(2) Uiso 1 d . . F4 F 0.4300(9) 0.3125(9) -0.2045(7) 0.126(2) Uiso 1 d . . F5 F 0.4024(11) 0.4671(11) -0.0842(9) 0.152(3) Uiso 1 d . . F6 F 0.2288(11) 0.4823(11) -0.1901(9) 0.151(3) Uiso 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 0.0506(3) 0.0460(3) 0.0405(3) -0.0032(2) -0.0034(2) -0.0213(2) N1 0.057(3) 0.044(3) 0.044(3) -0.001(2) -0.002(2) -0.021(2) N2 0.056(3) 0.045(3) 0.046(3) -0.008(2) -0.004(2) -0.021(2) O1 0.059(3) 0.053(3) 0.062(3) -0.001(2) -0.013(2) -0.024(2) O3 0.066(3) 0.052(3) 0.052(3) -0.001(2) 0.004(2) -0.023(2) C1 0.065(4) 0.061(4) 0.049(4) 0.001(3) -0.008(3) -0.033(4) C2 0.063(4) 0.049(4) 0.053(4) -0.001(3) -0.009(3) -0.028(3) C3 0.084(6) 0.075(5) 0.069(5) 0.010(4) -0.024(4) -0.049(5) C4 0.089(6) 0.062(5) 0.068(5) 0.000(4) -0.027(4) -0.038(4) C5 0.084(5) 0.066(5) 0.053(4) -0.007(4) -0.026(4) -0.025(4) C6 0.065(4) 0.051(4) 0.045(3) -0.001(3) -0.007(3) -0.019(3) C7 0.089(6) 0.070(5) 0.065(5) -0.016(4) -0.009(5) 0.005(5) C8 0.079(6) 0.096(7) 0.066(5) -0.019(5) -0.003(5) 0.004(5) C9 0.055(4) 0.048(4) 0.045(3) 0.003(3) 0.001(3) -0.015(3) C10 0.076(5) 0.050(4) 0.059(4) -0.002(3) -0.009(4) -0.031(4) C11 0.060(4) 0.044(3) 0.060(4) -0.011(3) 0.001(3) -0.019(3) C12 0.054(4) 0.065(4) 0.059(4) -0.010(4) 0.006(3) -0.010(3) C2,1 0.063(4) 0.052(4) 0.044(3) -0.004(3) -0.004(3) -0.019(3) C3,1 0.063(4) 0.059(4) 0.051(4) 0.008(3) -0.014(3) -0.022(3) C4,1 0.085(5) 0.070(5) 0.040(3) 0.000(3) -0.005(3) -0.042(4) C5,1 0.076(5) 0.063(4) 0.042(4) -0.007(3) 0.003(3) -0.022(4) C6,1 0.064(4) 0.056(4) 0.044(3) -0.003(3) -0.002(3) -0.018(3) C1,1 0.052(3) 0.046(3) 0.042(3) -0.001(3) -0.005(3) -0.025(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 N1 1.989(5) . ? Pd1 N2 1.989(5) . ? Pd1 O3 2.000(5) . ? Pd1 O1 2.000(5) . ? N1 C1 1.262(9) . ? N1 C1,1 1.417(6) . ? N2 C6 1.328(9) . ? N2 C2 1.356(9) . ? O1 C9 1.272(8) . ? O3 C11 1.267(9) . ? O2 C9 1.202(9) . ? O4 C11 1.198(10) . ? C1 C2 1.464(9) . ? C2 C3 1.357(10) . ? C3 C4 1.389(11) . ? C4 C5 1.347(12) . ? C5 C6 1.388(11) . ? C7 C2,1 1.512(9) . ? C8 C6,1 1.525(9) . ? C9 C10 1.509(10) . ? C10 F1 1.303(10) . ? C10 F3 1.322(11) . ? C10 F2 1.335(10) . ? C11 C12 1.476(11) . ? C12 F6 1.242(11) . ? C12 F4 1.284(10) . ? C12 F5 1.346(12) . ? C2,1 C3,1 1.3900 . ? C2,1 C1,1 1.3900 . ? C3,1 C4,1 1.3900 . ? C4,1 C5,1 1.3900 . ? C5,1 C6,1 1.3900 . ? C6,1 C1,1 1.3900 . ? 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 Pd1 N2 81.0(2) . . ? N1 Pd1 O3 176.4(2) . . ? N2 Pd1 O3 96.0(2) . . ? N1 Pd1 O1 94.3(2) . . ? N2 Pd1 O1 173.7(2) . . ? O3 Pd1 O1 88.9(2) . . ? C1 N1 C1,1 121.5(6) . . ? C1 N1 Pd1 114.5(5) . . ? C1,1 N1 Pd1 124.0(4) . . ? C6 N2 C2 118.8(6) . . ? C6 N2 Pd1 127.5(5) . . ? C2 N2 Pd1 113.7(4) . . ? C9 O1 Pd1 116.3(4) . . ? C11 O3 Pd1 118.0(4) . . ? N1 C1 C2 117.9(6) . . ? N2 C2 C3 122.0(7) . . ? N2 C2 C1 112.7(6) . . ? C3 C2 C1 125.3(7) . . ? C2 C3 C4 119.2(8) . . ? C5 C4 C3 118.6(7) . . ? C4 C5 C6 120.5(7) . . ? N2 C6 C5 120.9(7) . . ? O2 C9 O1 128.2(7) . . ? O2 C9 C10 119.3(7) . . ? O1 C9 C10 112.5(6) . . ? F1 C10 F3 108.2(7) . . ? F1 C10 F2 106.8(7) . . ? F3 C10 F2 105.4(7) . . ? F1 C10 C9 112.5(7) . . ? F3 C10 C9 114.1(7) . . ? F2 C10 C9 109.5(6) . . ? O4 C11 O3 127.2(8) . . ? O4 C11 C12 118.7(7) . . ? O3 C11 C12 114.0(6) . . ? F6 C12 F4 110.8(9) . . ? F6 C12 F5 101.4(9) . . ? F4 C12 F5 104.6(8) . . ? F6 C12 C11 114.7(8) . . ? F4 C12 C11 113.9(7) . . ? F5 C12 C11 110.3(8) . . ? C3,1 C2,1 C1,1 120.0 . . ? C3,1 C2,1 C7 119.9(4) . . ? C1,1 C2,1 C7 120.1(4) . . ? C2,1 C3,1 C4,1 120.0 . . ? C5,1 C4,1 C3,1 120.0 . . ? C4,1 C5,1 C6,1 120.0 . . ? C1,1 C6,1 C5,1 120.0 . . ? C1,1 C6,1 C8 120.5(4) . . ? C5,1 C6,1 C8 119.5(4) . . ? C6,1 C1,1 C2,1 120.0 . . ? C6,1 C1,1 N1 119.8(3) . . ? C2,1 C1,1 N1 119.9(4) . . ? _refine_diff_density_max 1.420 _refine_diff_density_min -1.074 _refine_diff_density_rms 0.142 #END data_2a _database_code_CSD 178391 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H16 F6 N2 O4 Pd' _chemical_formula_weight 556.74 _chemical_melting_point ? _chemical_compound_source ? 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' 'F' 'F' 0.0171 0.0103 '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 ? _symmetry_space_group_name_H-M ? 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 8.481(4) _cell_length_b 20.641(4) _cell_length_c 12.241(3) _cell_angle_alpha 90.00(2) _cell_angle_beta 98.80(2) _cell_angle_gamma 90.00(2) _cell_volume 2117.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method ? _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.957 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3709 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3709 _reflns_number_observed 2763 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1709P)^2^+2.7664P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3709 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_obs 0.0667 _refine_ls_wR_factor_all 0.2418 _refine_ls_wR_factor_obs 0.2114 _refine_ls_goodness_of_fit_all 1.072 _refine_ls_goodness_of_fit_obs 1.097 _refine_ls_restrained_S_all 1.072 _refine_ls_restrained_S_obs 1.097 _refine_ls_shift/esd_max 0.064 _refine_ls_shift/esd_mean 0.009 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Pd1 Pd 1.12079(7) 0.11762(3) 0.24259(5) 0.0409(3) Uani 1 d . . N1 N 0.9113(8) 0.1581(3) 0.1863(5) 0.0395(15) Uani 1 d . . N2 N 1.0253(11) 0.1216(4) 0.3816(6) 0.055(2) Uani 1 d . . O1 O 1.1949(9) 0.1087(3) 0.0946(6) 0.0580(17) Uani 1 d . . O3 O 1.3400(7) 0.0835(3) 0.3093(6) 0.0562(16) Uani 1 d . . O2 O 1.2802(10) 0.2107(4) 0.0947(6) 0.073(2) Uani 1 d . . O4 O 1.2539(12) -0.0169(4) 0.2908(8) 0.092(3) Uani 1 d . . C1 C 0.8182(11) 0.1680(4) 0.2571(6) 0.0420(19) Uani 1 d . . C2 C 0.8822(10) 0.1474(4) 0.3706(7) 0.0429(18) Uani 1 d . . C3 C 0.8063(13) 0.1553(5) 0.4604(8) 0.059(3) Uani 1 d . . H3 H 0.7078 0.1760 0.4517 0.056(10) Uiso 1 calc R . C4 C 0.8720(15) 0.1332(6) 0.5631(8) 0.068(3) Uani 1 d . . H4 H 0.8182 0.1367 0.6236 0.056(10) Uiso 1 calc R . C5 C 1.0248(16) 0.1051(7) 0.5725(9) 0.076(3) Uani 1 d . . H5 H 1.0748 0.0906 0.6411 0.056(10) Uiso 1 calc R . C6 C 1.1025(16) 0.0988(6) 0.4800(8) 0.072(3) Uani 1 d . . H6 H 1.2028 0.0798 0.4855 0.056(10) Uiso 1 calc R . C7 C 0.9427(14) 0.2919(5) 0.1339(9) 0.063(3) Uani 1 d . . H7A H 1.0102 0.2718 0.1946 0.081(12) Uiso 1 calc R . H7B H 0.8500 0.3095 0.1593 0.081(12) Uiso 1 calc R . H7C H 1.0002 0.3261 0.1042 0.081(12) Uiso 1 calc R . C8 C 0.8107(15) 0.0612(5) 0.0222(9) 0.068(3) Uani 1 d . . H8A H 0.8953 0.0492 0.0800 0.081(12) Uiso 1 calc R . H8B H 0.8147 0.0343 -0.0413 0.081(12) Uiso 1 calc R . H8C H 0.7098 0.0554 0.0474 0.081(12) Uiso 1 calc R . C9 C 0.6568(11) 0.1961(6) 0.2299(8) 0.059(3) Uani 1 d . . H9A H 0.6465 0.2320 0.2782 0.081(12) Uiso 1 calc R . H9B H 0.5786 0.1638 0.2393 0.081(12) Uiso 1 calc R . H9C H 0.6404 0.2108 0.1546 0.081(12) Uiso 1 calc R . C10 C 1.2596(9) 0.1557(5) 0.0554(7) 0.048(2) Uani 1 d . . C11 C 1.3172(16) 0.1405(7) -0.0527(9) 0.076(3) Uani 1 d . . C12 C 1.3545(12) 0.0233(5) 0.3069(8) 0.053(2) Uani 1 d . . C13 C 1.5265(15) 0.0003(6) 0.3250(12) 0.077(3) Uani 1 d . . C1,1 C 0.8736(9) 0.1775(4) 0.0715(6) 0.0368(17) Uani 1 d . . C2,1 C 0.8920(10) 0.2422(4) 0.0453(7) 0.0436(19) Uani 1 d . . C3,1 C 0.8622(10) 0.2587(5) -0.0658(8) 0.053(2) Uani 1 d . . H3,1 H 0.8729 0.3017 -0.0865 0.056(10) Uiso 1 calc R . C4,1 C 0.8174(11) 0.2130(6) -0.1454(8) 0.059(3) Uani 1 d . . H4,1 H 0.7970 0.2251 -0.2194 0.056(10) Uiso 1 calc R . C5,1 C 0.8025(12) 0.1496(6) -0.1166(8) 0.063(3) Uani 1 d . . H5,1 H 0.7735 0.1191 -0.1720 0.056(10) Uiso 1 calc R . C6,1 C 0.8293(11) 0.1292(4) -0.0076(7) 0.048(2) Uani 1 d . . F1 F 1.1999(12) 0.1282(9) -0.1296(7) 0.200(8) Uani 1 d . . F2 F 1.4158(14) 0.0938(6) -0.0450(9) 0.140(4) Uani 1 d . . F3 F 1.3962(17) 0.1860(6) -0.0867(10) 0.163(5) Uani 1 d . . F4 F 1.6102(12) 0.0238(7) 0.4163(12) 0.164(5) Uani 1 d . . F5 F 1.6154(12) 0.0286(7) 0.2567(11) 0.167(6) Uani 1 d . . F6 F 1.5485(14) -0.0576(4) 0.3224(16) 0.200(7) Uani 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 0.0398(4) 0.0413(5) 0.0417(4) 0.0055(3) 0.0066(3) 0.0087(3) N1 0.044(4) 0.036(4) 0.038(3) 0.000(3) 0.002(3) 0.007(3) N2 0.077(6) 0.045(5) 0.040(4) 0.007(3) -0.001(4) -0.002(4) O1 0.076(5) 0.049(4) 0.051(4) -0.003(3) 0.013(3) 0.009(3) O3 0.049(4) 0.048(4) 0.068(4) 0.002(3) -0.001(3) 0.010(3) O2 0.084(5) 0.061(5) 0.075(5) -0.003(4) 0.018(4) -0.011(4) O4 0.093(6) 0.061(5) 0.119(7) -0.008(5) 0.005(5) -0.015(5) C1 0.051(5) 0.039(5) 0.038(4) 0.002(3) 0.010(4) 0.005(4) C2 0.040(4) 0.045(5) 0.044(4) -0.005(4) 0.008(3) 0.005(4) C3 0.061(6) 0.061(6) 0.061(6) 0.000(5) 0.025(5) 0.013(5) C4 0.074(7) 0.091(9) 0.044(5) 0.005(5) 0.024(5) 0.008(6) C5 0.080(8) 0.101(9) 0.049(6) 0.021(6) 0.017(5) 0.017(7) C6 0.089(8) 0.075(8) 0.046(5) 0.011(5) -0.009(5) 0.022(6) C7 0.073(7) 0.039(5) 0.072(6) -0.001(5) -0.001(5) -0.001(5) C8 0.087(8) 0.043(6) 0.071(7) -0.006(5) 0.005(6) -0.006(5) C9 0.048(5) 0.072(7) 0.058(5) -0.002(5) 0.011(4) 0.014(5) C10 0.027(4) 0.063(6) 0.054(5) 0.010(5) 0.005(3) 0.013(4) C11 0.074(8) 0.099(10) 0.060(7) 0.020(6) 0.024(6) 0.005(7) C12 0.066(6) 0.044(6) 0.050(5) 0.008(4) 0.014(4) 0.005(5) C13 0.064(7) 0.068(8) 0.098(9) 0.018(7) 0.010(7) 0.023(6) C1,1 0.033(4) 0.043(5) 0.033(4) 0.004(3) -0.001(3) 0.004(3) C2,1 0.038(4) 0.035(5) 0.056(5) 0.001(4) 0.003(4) 0.010(3) C3,1 0.040(5) 0.054(6) 0.065(6) 0.024(5) 0.008(4) 0.008(4) C4,1 0.043(5) 0.082(7) 0.049(5) 0.015(5) 0.000(4) -0.002(5) C5,1 0.059(6) 0.086(8) 0.041(5) -0.009(5) -0.001(4) -0.004(6) C6,1 0.046(5) 0.050(5) 0.049(5) -0.003(4) 0.006(4) -0.007(4) F1 0.080(6) 0.46(3) 0.061(5) -0.060(8) 0.011(4) 0.016(9) F2 0.156(9) 0.150(9) 0.133(8) 0.002(7) 0.086(7) 0.067(8) F3 0.221(13) 0.149(10) 0.155(9) 0.003(8) 0.140(10) -0.020(9) F4 0.087(6) 0.175(11) 0.211(13) -0.030(10) -0.034(7) 0.024(7) F5 0.119(8) 0.177(12) 0.225(14) 0.068(9) 0.093(9) 0.067(8) F6 0.130(9) 0.053(5) 0.41(2) 0.028(9) 0.017(11) 0.046(6) _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 N1 1.989(7) . ? Pd1 N2 1.995(9) . ? Pd1 O1 2.014(7) . ? Pd1 O3 2.039(6) . ? N1 C1 1.275(10) . ? N1 C1,1 1.449(9) . ? N2 C2 1.313(13) . ? N2 C6 1.364(12) . ? O1 C10 1.247(12) . ? O3 C12 1.250(12) . ? O2 C10 1.233(12) . ? O4 C12 1.185(13) . ? C1 C2 1.475(11) . ? C1 C9 1.478(12) . ? C2 C3 1.365(12) . ? C3 C4 1.373(15) . ? C4 C5 1.409(18) . ? C5 C6 1.401(16) . ? C7 C2,1 1.506(13) . ? C8 C6,1 1.466(13) . ? C10 C11 1.512(14) . ? C11 F3 1.261(16) . ? C11 F2 1.270(16) . ? C11 F1 1.286(16) . ? C12 C13 1.517(15) . ? C13 F6 1.210(14) . ? C13 F4 1.320(17) . ? C13 F5 1.343(16) . ? C1,1 C2,1 1.388(12) . ? C1,1 C6,1 1.400(12) . ? C2,1 C3,1 1.387(13) . ? C3,1 C4,1 1.369(15) . ? C4,1 C5,1 1.366(16) . ? C5,1 C6,1 1.384(13) . ? 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 Pd1 N2 79.7(3) . . ? N1 Pd1 O1 96.4(3) . . ? N2 Pd1 O1 173.7(3) . . ? N1 Pd1 O3 174.7(3) . . ? N2 Pd1 O3 97.9(3) . . ? O1 Pd1 O3 86.4(3) . . ? C1 N1 C1,1 123.2(7) . . ? C1 N1 Pd1 116.4(5) . . ? C1,1 N1 Pd1 120.3(5) . . ? C2 N2 C6 122.8(9) . . ? C2 N2 Pd1 114.8(6) . . ? C6 N2 Pd1 122.4(8) . . ? C10 O1 Pd1 119.4(6) . . ? C12 O3 Pd1 114.9(6) . . ? N1 C1 C2 114.7(7) . . ? N1 C1 C9 124.0(7) . . ? C2 C1 C9 121.3(7) . . ? N2 C2 C3 120.6(8) . . ? N2 C2 C1 114.4(7) . . ? C3 C2 C1 125.0(8) . . ? C2 C3 C4 121.5(10) . . ? C3 C4 C5 116.8(9) . . ? C6 C5 C4 120.8(10) . . ? N2 C6 C5 117.4(11) . . ? O2 C10 O1 127.6(9) . . ? O2 C10 C11 119.1(10) . . ? O1 C10 C11 113.2(10) . . ? F3 C11 F2 102.3(12) . . ? F3 C11 F1 107.2(13) . . ? F2 C11 F1 109.4(15) . . ? F3 C11 C10 113.1(12) . . ? F2 C11 C10 113.0(10) . . ? F1 C11 C10 111.4(10) . . ? O4 C12 O3 129.0(10) . . ? O4 C12 C13 117.2(10) . . ? O3 C12 C13 113.8(10) . . ? F6 C13 F4 108.6(13) . . ? F6 C13 F5 108.0(14) . . ? F4 C13 F5 95.0(13) . . ? F6 C13 C12 116.9(13) . . ? F4 C13 C12 113.0(11) . . ? F5 C13 C12 113.1(10) . . ? C2,1 C1,1 C6,1 123.6(7) . . ? C2,1 C1,1 N1 118.4(7) . . ? C6,1 C1,1 N1 117.9(7) . . ? C3,1 C2,1 C1,1 116.9(8) . . ? C3,1 C2,1 C7 121.9(9) . . ? C1,1 C2,1 C7 121.2(8) . . ? C4,1 C3,1 C2,1 121.2(9) . . ? C5,1 C4,1 C3,1 120.2(9) . . ? C4,1 C5,1 C6,1 122.1(10) . . ? C5,1 C6,1 C1,1 115.9(9) . . ? C5,1 C6,1 C8 121.5(9) . . ? C1,1 C6,1 C8 122.6(8) . . ? _refine_diff_density_max 1.329 _refine_diff_density_min -1.269 _refine_diff_density_rms 0.210 #END data_3a _database_code_CSD 178392 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H22 F6 N2 O4 Pd' _chemical_formula_weight 598.84 _chemical_melting_point ? _chemical_compound_source ? 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' 'F' 'F' 0.0171 0.0103 '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 ? _symmetry_space_group_name_H-M ? 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 12.370(4) _cell_length_b 17.071(2) _cell_length_c 12.663(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 105.55(4) _cell_angle_gamma 90.000(5) _cell_volume 2576.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method ? _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4725 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.97 _reflns_number_total 4509 _reflns_number_observed 3244 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1588P)^2^+17.9465P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4509 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_obs 0.0752 _refine_ls_wR_factor_all 0.2473 _refine_ls_wR_factor_obs 0.2123 _refine_ls_goodness_of_fit_all 0.954 _refine_ls_goodness_of_fit_obs 0.974 _refine_ls_restrained_S_all 0.954 _refine_ls_restrained_S_obs 0.974 _refine_ls_shift/esd_max 14.119 _refine_ls_shift/esd_mean 0.212 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Pd1 Pd 1.04494(5) 0.12413(4) 0.95694(5) 0.0397(3) Uani 1 d . . N1 N 1.0196(6) 0.2000(4) 0.8336(6) 0.0441(17) Uani 1 d . . N2 N 0.8812(7) 0.1403(5) 0.9321(6) 0.0463(19) Uani 1 d . . O1 O 1.2050(5) 0.1038(4) 0.9580(6) 0.0534(17) Uani 1 d . . O2 O 1.0710(6) 0.0540(4) 1.0905(5) 0.0491(16) Uani 1 d . . O3 O 1.2770(7) 0.1759(6) 1.1054(8) 0.090(3) Uani 1 d . . O4 O 1.0482(7) 0.1561(5) 1.1949(7) 0.074(2) Uani 1 d . . C1 C 0.9176(9) 0.2228(6) 0.7967(9) 0.056(3) Uani 1 d . . H1 H 0.8968 0.2587 0.7395 0.09(2) Uiso 1 calc R . C2 C 0.8362(8) 0.1900(6) 0.8483(8) 0.049(2) Uani 1 d . . C3 C 0.7247(10) 0.2087(8) 0.8180(11) 0.073(3) Uani 1 d . . H3 H 0.6961 0.2438 0.7613 0.09(2) Uiso 1 calc R . C4 C 0.6556(10) 0.1738(10) 0.8742(12) 0.085(4) Uani 1 d . . H4 H 0.5791 0.1847 0.8553 0.09(2) Uiso 1 calc R . C5 C 0.7005(10) 0.1235(9) 0.9568(12) 0.078(4) Uani 1 d . . H5 H 0.6545 0.1001 0.9950 0.09(2) Uiso 1 calc R . C6 C 0.8141(9) 0.1066(7) 0.9853(10) 0.061(3) Uani 1 d . . H6 H 0.8437 0.0715 1.0418 0.09(2) Uiso 1 calc R . C7 C 1.1030(14) 0.3444(9) 0.9337(11) 0.085(4) Uani 1 d . . C8 C 1.034(2) 0.4130(17) 0.8801(18) 0.164(10) Uani 1 d . . H8A H 1.0763 0.4604 0.9013 0.17(3) Uiso 1 calc R . H8B H 0.9663 0.4153 0.9027 0.17(3) Uiso 1 calc R . H8C H 1.0165 0.4072 0.8019 0.17(3) Uiso 1 calc R . C9 C 1.191(2) 0.3762(11) 1.0333(16) 0.136(8) Uani 1 d . . H9A H 1.2008 0.4314 1.0243 0.17(3) Uiso 1 calc R . H9B H 1.2613 0.3499 1.0400 0.17(3) Uiso 1 calc R . H9C H 1.1670 0.3674 1.0983 0.17(3) Uiso 1 calc R . C10 C 1.1017(14) 0.1223(8) 0.6710(12) 0.084(4) Uani 1 d . . C11 C 1.0253(19) 0.1400(11) 0.5566(16) 0.128(7) Uani 1 d . . H11A H 0.9606 0.1685 0.5633 0.17(3) Uiso 1 calc R . H11B H 1.0018 0.0917 0.5184 0.17(3) Uiso 1 calc R . H11C H 1.0656 0.1708 0.5163 0.17(3) Uiso 1 calc R . C12 C 1.187(2) 0.0622(12) 0.6636(19) 0.157(10) Uani 1 d . . H12A H 1.2339 0.0824 0.6205 0.17(3) Uiso 1 calc R . H12B H 1.1499 0.0157 0.6298 0.17(3) Uiso 1 calc R . H12C H 1.2325 0.0500 0.7359 0.17(3) Uiso 1 calc R . C13 C 1.2842(9) 0.1337(7) 1.0316(10) 0.059(3) Uani 1 d . . C14 C 1.4025(11) 0.1347(14) 0.986(3) 0.24(2) Uani 1 d . . C15 C 1.0809(9) 0.0909(7) 1.1803(9) 0.056(3) Uani 1 d . . C16 C 1.1447(19) 0.0442(9) 1.2782(10) 0.110(7) Uani 1 d . . C2,1 C 1.1526(7) 0.3057(4) 0.8483(6) 0.071(3) Uani 1 d G . C3,1 C 1.2445(8) 0.3384(5) 0.8213(8) 0.096(5) Uani 1 d G . H3,1 H 1.2753 0.3851 0.8538 0.115 Uiso 1 calc R . C4,1 C 1.2906(6) 0.3014(6) 0.7457(9) 0.103(5) Uani 1 d G . H4,1 H 1.3521 0.3233 0.7277 0.124 Uiso 1 calc R . C5,1 C 1.2447(7) 0.2316(6) 0.6972(7) 0.097(5) Uani 1 d G . H5,1 H 1.2755 0.2068 0.6466 0.116 Uiso 1 calc R . C6,1 C 1.1527(7) 0.1989(4) 0.7242(6) 0.064(3) Uani 1 d G . C1,1 C 1.1066(5) 0.2359(4) 0.7997(6) 0.053(2) Uani 1 d G . F1 F 1.4740(16) 0.1497(11) 1.0740(15) 0.193(6) Uiso 1 d . . F2 F 1.4018(15) 0.0728(11) 0.9397(15) 0.202(6) Uiso 1 d . . F3 F 1.4325(10) 0.0510(7) 1.0791(10) 0.183(4) Uiso 1 d . . F4 F 1.2089(12) 0.0835(9) 1.3537(12) 0.164(5) Uiso 1 d . . F5 F 1.070(2) 0.0292(14) 1.341(2) 0.134(7) Uiso 0.50 d P . F6 F 1.1309(14) -0.0277(10) 1.2747(13) 0.181(5) Uiso 1 d . . F5* F 1.239(2) 0.0011(14) 1.2555(19) 0.129(7) Uiso 0.50 d P . 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 0.0339(4) 0.0434(4) 0.0389(4) -0.0012(3) 0.0045(3) 0.0002(3) N1 0.040(4) 0.044(4) 0.045(4) -0.001(3) 0.005(3) -0.002(3) N2 0.044(4) 0.053(5) 0.042(4) -0.009(4) 0.013(4) 0.001(4) O1 0.035(3) 0.067(4) 0.056(4) -0.003(3) 0.009(3) 0.005(3) O2 0.054(4) 0.047(4) 0.041(4) -0.001(3) 0.002(3) 0.001(3) O3 0.051(5) 0.123(8) 0.092(7) -0.050(6) 0.011(4) -0.014(5) O4 0.065(5) 0.079(6) 0.078(6) -0.023(5) 0.022(4) 0.007(4) C1 0.062(7) 0.051(6) 0.048(6) 0.001(5) 0.002(5) -0.002(5) C2 0.042(5) 0.045(5) 0.057(6) -0.002(4) 0.008(4) 0.003(4) C3 0.049(6) 0.074(8) 0.082(8) 0.010(7) -0.008(6) 0.016(6) C4 0.040(7) 0.120(12) 0.092(10) -0.002(9) 0.011(7) 0.009(7) C5 0.047(6) 0.108(11) 0.087(9) 0.011(8) 0.031(6) -0.005(7) C6 0.050(6) 0.071(7) 0.064(7) -0.002(6) 0.017(5) 0.000(5) C7 0.101(11) 0.084(9) 0.065(8) -0.028(7) 0.012(8) -0.020(8) C8 0.142(19) 0.22(3) 0.119(17) -0.082(19) 0.019(14) 0.028(19) C9 0.155(19) 0.139(17) 0.088(12) -0.038(11) -0.013(12) -0.019(13) C10 0.119(12) 0.068(8) 0.079(9) -0.016(7) 0.049(9) 0.002(8) C11 0.135(18) 0.110(14) 0.113(15) -0.019(11) -0.012(13) -0.023(12) C12 0.18(2) 0.108(15) 0.16(2) -0.040(14) 0.001(17) 0.054(15) C13 0.040(5) 0.063(7) 0.065(7) -0.005(6) 0.000(5) 0.003(5) C14 0.031(7) 0.22(2) 0.39(4) -0.23(3) -0.073(13) 0.046(10) C15 0.052(6) 0.067(7) 0.050(6) -0.001(5) 0.013(5) -0.016(5) C16 0.20(2) 0.075(9) 0.036(6) -0.014(6) -0.005(9) -0.042(11) C2,1 0.076(8) 0.065(7) 0.062(7) 0.009(6) 0.004(6) -0.022(6) C3,1 0.094(11) 0.092(10) 0.091(11) 0.001(9) 0.005(9) -0.044(9) C4,1 0.088(11) 0.122(14) 0.105(13) 0.029(11) 0.035(10) -0.025(10) C5,1 0.079(10) 0.140(14) 0.079(9) 0.026(9) 0.035(8) 0.008(10) C6,1 0.067(7) 0.069(7) 0.059(7) 0.010(6) 0.021(6) 0.005(6) C1,1 0.057(6) 0.054(6) 0.043(5) 0.009(5) 0.004(5) -0.003(5) _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 1.984(8) . ? Pd1 N1 1.987(8) . ? Pd1 O1 2.006(6) . ? Pd1 O2 2.026(6) . ? N1 C1 1.283(13) . ? N1 C1,1 1.403(9) . ? N2 C6 1.331(14) . ? N2 C2 1.357(13) . ? O1 C13 1.265(13) . ? O2 C15 1.277(13) . ? O3 C13 1.203(14) . ? O4 C15 1.214(14) . ? C1 C2 1.452(15) . ? C2 C3 1.366(15) . ? C3 C4 1.386(19) . ? C4 C5 1.35(2) . ? C5 C6 1.385(17) . ? C7 C8 1.50(3) . ? C7 C2,1 1.528(16) . ? C7 C9 1.53(2) . ? C10 C12 1.49(2) . ? C10 C11 1.53(2) . ? C10 C6,1 1.528(15) . ? C13 C14 1.71(3) . ? C14 F2 1.20(2) . ? C14 F1 1.25(3) . ? C14 F3 1.83(4) . ? C15 C16 1.508(19) . ? C16 F6 1.238(19) . ? C16 F4 1.260(18) . ? C16 F5 1.40(3) . ? C16 F5* 1.47(3) . ? C2,1 C3,1 1.3900 . ? C2,1 C1,1 1.3900 . ? C3,1 C4,1 1.3900 . ? C4,1 C5,1 1.3900 . ? C5,1 C6,1 1.3900 . ? C6,1 C1,1 1.3900 . ? F1 F3 1.77(2) . ? F2 F3 1.743(19) . ? F5 F6 1.60(3) . ? F6 F5* 1.50(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 N2 Pd1 N1 81.1(3) . . ? N2 Pd1 O1 171.4(3) . . ? N1 Pd1 O1 93.8(3) . . ? N2 Pd1 O2 98.2(3) . . ? N1 Pd1 O2 175.6(3) . . ? O1 Pd1 O2 87.5(3) . . ? C1 N1 C1,1 121.0(8) . . ? C1 N1 Pd1 114.7(7) . . ? C1,1 N1 Pd1 123.6(6) . . ? C6 N2 C2 119.1(9) . . ? C6 N2 Pd1 127.4(7) . . ? C2 N2 Pd1 113.5(6) . . ? C13 O1 Pd1 120.2(7) . . ? C15 O2 Pd1 114.1(7) . . ? N1 C1 C2 116.8(9) . . ? C3 C2 N2 122.4(10) . . ? C3 C2 C1 123.6(10) . . ? N2 C2 C1 113.9(9) . . ? C2 C3 C4 118.2(11) . . ? C5 C4 C3 119.2(11) . . ? C4 C5 C6 120.8(12) . . ? N2 C6 C5 120.3(11) . . ? C8 C7 C2,1 107.6(13) . . ? C8 C7 C9 106.8(15) . . ? C2,1 C7 C9 113.9(15) . . ? C12 C10 C11 110.1(14) . . ? C12 C10 C6,1 113.5(15) . . ? C11 C10 C6,1 109.0(11) . . ? O3 C13 O1 127.5(10) . . ? O3 C13 C14 120.4(10) . . ? O1 C13 C14 108.5(11) . . ? F2 C14 F1 121(2) . . ? F2 C14 C13 105.0(19) . . ? F1 C14 C13 99(2) . . ? F2 C14 F3 66.5(17) . . ? F1 C14 F3 67.0(18) . . ? C13 C14 F3 79.4(18) . . ? O4 C15 O2 129.2(11) . . ? O4 C15 C16 118.8(11) . . ? O2 C15 C16 112.1(11) . . ? F6 C16 F4 127.5(18) . . ? F6 C16 F5 74.6(15) . . ? F4 C16 F5 92.4(15) . . ? F6 C16 F5* 66.8(14) . . ? F4 C16 F5* 92.5(19) . . ? F5 C16 F5* 134.5(18) . . ? F6 C16 C15 117.3(13) . . ? F4 C16 C15 115.2(14) . . ? F5 C16 C15 106.6(19) . . ? F5* C16 C15 111.8(15) . . ? C3,1 C2,1 C1,1 120.0 . . ? C3,1 C2,1 C7 120.7(8) . . ? C1,1 C2,1 C7 119.3(8) . . ? C2,1 C3,1 C4,1 120.0 . . ? C5,1 C4,1 C3,1 120.0 . . ? C6,1 C5,1 C4,1 120.0 . . ? C1,1 C6,1 C5,1 120.0 . . ? C1,1 C6,1 C10 119.7(8) . . ? C5,1 C6,1 C10 120.3(7) . . ? C6,1 C1,1 C2,1 120.0 . . ? C6,1 C1,1 N1 120.1(6) . . ? C2,1 C1,1 N1 119.7(6) . . ? C14 F1 F3 72.3(18) . . ? C14 F2 F3 74(2) . . ? F2 F3 F1 75.3(9) . . ? F2 F3 C14 39.3(8) . . ? F1 F3 C14 40.7(7) . . ? C16 F5 F6 48.2(11) . . ? C16 F6 F5* 64.0(15) . . ? C16 F6 F5 57.3(14) . . ? F5* F6 F5 116.7(17) . . ? C16 F5* F6 49.3(11) . . ? _refine_diff_density_max 1.656 _refine_diff_density_min -1.379 _refine_diff_density_rms 0.153 END