Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name 'Carsten D. Brandt' 'Martin Broring' _publ_contact_author_name 'Dr Martin Broring' _publ_contact_author_address ; Institut fur Anoganische Chemie Universitat Wurzburg Am Hubland D-97074 Wurzburg GERMANY ; _publ_contact_author_phone '049 931 888 5267' _publ_contact_author_fax '049 931 888 4605' _publ_contact_author_email Martin.Broering@mail.uni-wuerzburg.de _publ_requested_journal 'J. Chem. Soc., Dalton Trans.' _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication in "J. Chem. Soc., Dalton Trans." ; _publ_section_title ; One compound, two structures: synthesis, structures and reactivity of a novel tripyrrinatopalladium(II)-trifluoracetate complex TrpyPdOAcf ; _publ_section_abstract ; Summary The novel (1,14-dimethyl-3,4,13,14-tetraethyltripyrrinato)palladium(II) trifluoroacetate (TrpyPdOAcf) 7 was found to exhibit two different geometries in the solid state. While in one crystal the tripyrrin ligand is helically distorted to ensure a square-planar coordination of the central palladium(II) ion, the bonding geometry of the metal centre of the other geometrical isomer found in a different crystal shows a pronounced tetrahedral deviation from planarity, accompanied with an almost planar tripyrrolic ligand. In solution, nonplanar structures of 7 can not be detected as judged by the results of variable temperature proton nmr spectroscopy. The energy stored in the strained complexes 6 and 7, however, becomes "visible" in fast ligand exchange processes, which enable us to prepare a number of new TrpyPdX complexes with X = Cl, Br, I, N3, NCO, SCN and OAc, of which the latter two decompose in solution. As the x-ray crystallographic analysis of TrpyPdBr 9 demonstrates, complexes with a tilted fourth ligand are predominant in the solid state with donor atoms larger than oxygen. ; _publ_section_exptl_prep ; Crystals were grown by slow concentration from a solution in dichloromethane layered with hexane at room temperature. ; _publ_section_exptl_refinement ; The carbon atoms C22 C23 C8 were refined with restraints to have the same U(ij) components (SIMU) and to have the same components of the anisotropic displacement parameters in the direction of the bond (DELU). The remaining electron densities are less than 1 Angstrom away from C22 and C23. ; data_cb1cbmon _database_code_CSD 172679 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '147_C (dec.)' _chemical_formula_moiety ? _chemical_formula_sum 'C28 H38 Br N3 Pd' _chemical_formula_weight 602.92 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' 'Pd' 'Pd' -0.9988 1.0072 '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_Int_Tables_number 15 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 15.392(3) _cell_length_b 17.056(3) _cell_length_c 21.450(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.80(3) _cell_angle_gamma 90.00 _cell_volume 5361.8(19) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 2.203 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'IPDS (STOE)' _diffrn_measurement_method 'IPDS (STOE)' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21727 _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4732 _reflns_number_gt 3748 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE)' _computing_cell_refinement 'IPDS (STOE)' _computing_data_reduction 'IPDS (STOE)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0667P)^2^+0.0000P] 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 4732 _refine_ls_number_parameters 306 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.070 _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 Pd Pd 0.33463(2) 0.127928(19) 0.547242(14) 0.02745(12) Uani 1 1 d . . . Br Br 0.35632(3) 0.05635(3) 0.65085(2) 0.04434(16) Uani 1 1 d . . . N1 N 0.4710(2) 0.1284(2) 0.56031(16) 0.0280(7) Uani 1 1 d . . . N2 N 0.3086(2) 0.1232(2) 0.44870(16) 0.0315(8) Uani 1 1 d . . . N3 N 0.2007(2) 0.1496(2) 0.53671(18) 0.0355(8) Uani 1 1 d . . . C1 C 0.5391(3) 0.1454(3) 0.6144(2) 0.0320(9) Uani 1 1 d . . . C2 C 0.6263(3) 0.1278(3) 0.6056(2) 0.0343(10) Uani 1 1 d . . . C3 C 0.6093(3) 0.1020(3) 0.5427(2) 0.0327(9) Uani 1 1 d . . . C4 C 0.5113(3) 0.1041(2) 0.5130(2) 0.0273(9) Uani 1 1 d . . . C5 C 0.4650(3) 0.0908(2) 0.4492(2) 0.0275(8) Uani 1 1 d . . . H5 H 0.5003 0.0739 0.4224 0.033 Uiso 1 1 calc R . . C6 C 0.3701(3) 0.0992(3) 0.41785(19) 0.0310(9) Uani 1 1 d . . . C7 C 0.3242(3) 0.0779(3) 0.3519(2) 0.0411(11) Uani 1 1 d . . . C8 C 0.2323(4) 0.0874(5) 0.3436(3) 0.0698(17) Uani 1 1 d U . . C9 C 0.2244(3) 0.1144(4) 0.4044(2) 0.0488(13) Uani 1 1 d . . . C10 C 0.1419(3) 0.1245(4) 0.4198(2) 0.0552(15) Uani 1 1 d . . . H10 H 0.0877 0.1201 0.3839 0.066 Uiso 1 1 calc R . . C11 C 0.1294(3) 0.1395(3) 0.4778(2) 0.0414(11) Uani 1 1 d . . . C12 C 0.0437(3) 0.1563(3) 0.4913(3) 0.0452(12) Uani 1 1 d . . . C13 C 0.0649(3) 0.1774(3) 0.5543(2) 0.0407(11) Uani 1 1 d . . . C14 C 0.1636(3) 0.1750(3) 0.5809(2) 0.0375(10) Uani 1 1 d . . . C15 C 0.5280(3) 0.1790(3) 0.6750(2) 0.0427(11) Uani 1 1 d . . . H15A H 0.4636 0.1921 0.6678 0.064 Uiso 1 1 calc R . . H15B H 0.5651 0.2265 0.6869 0.064 Uiso 1 1 calc R . . H15C H 0.5477 0.1406 0.7106 0.064 Uiso 1 1 calc R . . C16 C 0.7172(3) 0.1373(3) 0.6577(3) 0.0458(12) Uani 1 1 d . . . H16A H 0.7087 0.1290 0.7012 0.055 Uiso 1 1 calc R . . H16B H 0.7594 0.0963 0.6516 0.055 Uiso 1 1 calc R . . C17 C 0.7603(4) 0.2167(4) 0.6570(3) 0.0664(17) Uani 1 1 d . . . H17A H 0.7738 0.2236 0.6155 0.100 Uiso 1 1 calc R . . H17B H 0.8170 0.2202 0.6935 0.100 Uiso 1 1 calc R . . H17C H 0.7180 0.2577 0.6614 0.100 Uiso 1 1 calc R . . C18 C 0.6764(3) 0.0767(3) 0.5089(2) 0.0394(11) Uani 1 1 d . . . H18A H 0.6520 0.0302 0.4816 0.047 Uiso 1 1 calc R . . H18B H 0.7339 0.0610 0.5423 0.047 Uiso 1 1 calc R . . C19 C 0.6974(4) 0.1402(3) 0.4658(3) 0.0578(15) Uani 1 1 d . . . H19A H 0.6410 0.1556 0.4321 0.087 Uiso 1 1 calc R . . H19B H 0.7412 0.1201 0.4448 0.087 Uiso 1 1 calc R . . H19C H 0.7236 0.1859 0.4927 0.087 Uiso 1 1 calc R . . C20 C 0.3682(3) 0.0522(3) 0.3018(2) 0.0484(13) Uani 1 1 d . . . H20A H 0.4265 0.0255 0.3243 0.058 Uiso 1 1 calc R . . H20B H 0.3280 0.0136 0.2721 0.058 Uiso 1 1 calc R . . C21 C 0.3866(5) 0.1186(4) 0.2620(3) 0.0707(18) Uani 1 1 d . . . H21A H 0.3294 0.1458 0.2400 0.106 Uiso 1 1 calc R . . H21B H 0.4130 0.0980 0.2290 0.106 Uiso 1 1 calc R . . H21C H 0.4296 0.1553 0.2907 0.106 Uiso 1 1 calc R . . C22 C 0.1533(5) 0.0607(6) 0.2828(3) 0.091(2) Uani 1 1 d U . . H22A H 0.1769 0.0264 0.2544 0.109 Uiso 1 1 calc R . . H22B H 0.1067 0.0314 0.2966 0.109 Uiso 1 1 calc R . . C23 C 0.1179(6) 0.1259(5) 0.2513(4) 0.097(2) Uani 1 1 d U . . H23A H 0.1006 0.1614 0.2815 0.146 Uiso 1 1 calc R . . H23B H 0.0638 0.1128 0.2147 0.146 Uiso 1 1 calc R . . H23C H 0.1632 0.1516 0.2346 0.146 Uiso 1 1 calc R . . C24 C -0.0492(3) 0.1480(4) 0.4414(3) 0.0594(16) Uani 1 1 d . . . H24A H -0.0464 0.1683 0.3988 0.071 Uiso 1 1 calc R . . H24B H -0.0931 0.1809 0.4551 0.071 Uiso 1 1 calc R . . C25 C -0.0848(4) 0.0648(4) 0.4319(3) 0.0740(19) Uani 1 1 d . . . H25A H -0.0396 0.0307 0.4219 0.111 Uiso 1 1 calc R . . H25B H -0.1419 0.0631 0.3956 0.111 Uiso 1 1 calc R . . H25C H -0.0961 0.0466 0.4721 0.111 Uiso 1 1 calc R . . C26 C 0.0014(4) 0.1997(3) 0.5925(3) 0.0559(14) Uani 1 1 d . . . H26A H -0.0583 0.2152 0.5615 0.067 Uiso 1 1 calc R . . H26B H 0.0267 0.2457 0.6203 0.067 Uiso 1 1 calc R . . C27 C -0.0132(6) 0.1337(5) 0.6354(4) 0.095(3) Uani 1 1 d . . . H27A H -0.0429 0.0896 0.6078 0.142 Uiso 1 1 calc R . . H27B H -0.0518 0.1521 0.6612 0.142 Uiso 1 1 calc R . . H27C H 0.0459 0.1167 0.6649 0.142 Uiso 1 1 calc R . . C28 C 0.2153(4) 0.2021(4) 0.6480(3) 0.0548(14) Uani 1 1 d . . . H28A H 0.2154 0.1606 0.6797 0.082 Uiso 1 1 calc R . . H28B H 0.1862 0.2492 0.6587 0.082 Uiso 1 1 calc R . . H28C H 0.2782 0.2144 0.6498 0.082 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 Pd 0.02740(17) 0.0366(2) 0.01920(17) 0.00240(13) 0.00833(12) 0.00204(13) Br 0.0515(3) 0.0543(3) 0.0288(2) 0.0121(2) 0.0146(2) 0.0022(2) N1 0.0294(17) 0.0319(18) 0.0224(17) -0.0017(14) 0.0077(14) -0.0027(14) N2 0.0268(17) 0.046(2) 0.0209(17) 0.0035(16) 0.0055(14) -0.0021(15) N3 0.0360(19) 0.042(2) 0.0305(19) 0.0064(16) 0.0133(16) 0.0064(16) C1 0.034(2) 0.035(2) 0.024(2) 0.0001(17) 0.0040(17) -0.0004(18) C2 0.031(2) 0.039(2) 0.029(2) 0.0020(19) 0.0037(18) 0.0010(18) C3 0.030(2) 0.033(2) 0.036(2) 0.0009(19) 0.0115(18) 0.0015(17) C4 0.0262(19) 0.028(2) 0.027(2) -0.0019(17) 0.0076(16) -0.0006(16) C5 0.032(2) 0.026(2) 0.027(2) -0.0003(17) 0.0132(17) -0.0015(16) C6 0.033(2) 0.040(2) 0.021(2) 0.0007(18) 0.0082(17) -0.0041(18) C7 0.040(2) 0.060(3) 0.025(2) -0.007(2) 0.0121(19) -0.012(2) C8 0.047(3) 0.131(5) 0.035(3) -0.015(3) 0.019(2) -0.017(3) C9 0.030(2) 0.091(4) 0.025(2) 0.001(2) 0.0087(19) -0.003(2) C10 0.027(2) 0.106(5) 0.028(2) 0.009(3) 0.0017(19) 0.003(3) C11 0.028(2) 0.061(3) 0.037(3) 0.013(2) 0.0116(19) 0.006(2) C12 0.032(2) 0.053(3) 0.054(3) 0.018(2) 0.018(2) 0.010(2) C13 0.042(2) 0.040(3) 0.047(3) 0.012(2) 0.024(2) 0.013(2) C14 0.040(2) 0.038(3) 0.039(2) 0.007(2) 0.019(2) 0.0096(19) C15 0.043(2) 0.057(3) 0.027(2) -0.009(2) 0.0090(19) -0.006(2) C16 0.035(2) 0.054(3) 0.040(3) -0.002(2) 0.000(2) 0.002(2) C17 0.041(3) 0.068(4) 0.081(4) -0.016(3) 0.007(3) -0.011(3) C18 0.029(2) 0.048(3) 0.042(3) -0.002(2) 0.0103(19) 0.0040(19) C19 0.058(3) 0.054(3) 0.077(4) -0.002(3) 0.042(3) 0.000(3) C20 0.046(3) 0.074(4) 0.026(2) -0.014(2) 0.014(2) -0.012(3) C21 0.094(5) 0.078(4) 0.058(4) 0.002(3) 0.049(4) 0.006(4) C22 0.072(4) 0.151(5) 0.048(3) -0.002(3) 0.016(3) 0.025(4) C23 0.092(5) 0.104(5) 0.092(5) 0.002(4) 0.023(4) -0.017(4) C24 0.029(2) 0.092(4) 0.056(3) 0.019(3) 0.012(2) 0.013(3) C25 0.045(3) 0.096(5) 0.075(4) -0.004(4) 0.009(3) 0.007(3) C26 0.052(3) 0.056(3) 0.073(4) 0.010(3) 0.039(3) 0.017(3) C27 0.109(6) 0.096(6) 0.119(7) 0.034(5) 0.095(6) 0.028(4) C28 0.060(3) 0.067(4) 0.043(3) -0.005(3) 0.024(2) 0.015(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 Pd N2 2.029(3) . ? Pd N1 2.032(3) . ? Pd N3 2.038(4) . ? Pd Br 2.4673(7) . ? N1 C1 1.336(5) . ? N1 C4 1.405(5) . ? N2 C9 1.362(6) . ? N2 C6 1.372(5) . ? N3 C14 1.320(6) . ? N3 C11 1.408(6) . ? C1 C2 1.443(6) . ? C1 C15 1.479(6) . ? C2 C3 1.365(6) . ? C2 C16 1.509(6) . ? C3 C4 1.446(6) . ? C3 C18 1.497(6) . ? C4 C5 1.354(6) . ? C5 C6 1.416(6) . ? C6 C7 1.422(6) . ? C7 C8 1.381(7) . ? C7 C20 1.500(7) . ? C8 C9 1.424(8) . ? C8 C22 1.554(9) . ? C9 C10 1.416(7) . ? C10 C11 1.339(7) . ? C11 C12 1.462(6) . ? C12 C13 1.340(7) . ? C12 C24 1.509(7) . ? C13 C14 1.451(6) . ? C13 C26 1.504(6) . ? C14 C28 1.489(7) . ? C16 C17 1.509(8) . ? C18 C19 1.522(8) . ? C20 C21 1.497(8) . ? C22 C23 1.329(11) . ? C24 C25 1.512(9) . ? C26 C27 1.513(9) . ? 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 Pd N1 90.58(14) . . ? N2 Pd N3 91.22(15) . . ? N1 Pd N3 169.23(15) . . ? N2 Pd Br 147.98(10) . . ? N1 Pd Br 91.61(10) . . ? N3 Pd Br 92.49(11) . . ? C1 N1 C4 106.8(3) . . ? C1 N1 Pd 128.6(3) . . ? C4 N1 Pd 124.4(3) . . ? C9 N2 C6 106.3(4) . . ? C9 N2 Pd 125.0(3) . . ? C6 N2 Pd 124.7(3) . . ? C14 N3 C11 107.2(4) . . ? C14 N3 Pd 128.6(3) . . ? C11 N3 Pd 124.1(3) . . ? N1 C1 C2 110.8(4) . . ? N1 C1 C15 125.2(4) . . ? C2 C1 C15 124.0(4) . . ? C3 C2 C1 106.9(4) . . ? C3 C2 C16 128.4(4) . . ? C1 C2 C16 124.7(4) . . ? C2 C3 C4 106.7(4) . . ? C2 C3 C18 128.2(4) . . ? C4 C3 C18 125.1(4) . . ? C5 C4 N1 124.5(4) . . ? C5 C4 C3 126.7(4) . . ? N1 C4 C3 108.6(3) . . ? C4 C5 C6 127.7(4) . . ? N2 C6 C5 124.3(4) . . ? N2 C6 C7 110.5(4) . . ? C5 C6 C7 125.0(4) . . ? C8 C7 C6 106.0(4) . . ? C8 C7 C20 127.7(4) . . ? C6 C7 C20 126.3(4) . . ? C7 C8 C9 106.9(5) . . ? C7 C8 C22 125.6(6) . . ? C9 C8 C22 126.8(5) . . ? N2 C9 C10 123.7(4) . . ? N2 C9 C8 110.2(4) . . ? C10 C9 C8 126.0(5) . . ? C11 C10 C9 129.3(4) . . ? C10 C11 N3 124.3(4) . . ? C10 C11 C12 128.0(4) . . ? N3 C11 C12 107.5(4) . . ? C13 C12 C11 107.2(4) . . ? C13 C12 C24 128.8(5) . . ? C11 C12 C24 124.0(5) . . ? C12 C13 C14 107.0(4) . . ? C12 C13 C26 128.3(5) . . ? C14 C13 C26 124.7(5) . . ? N3 C14 C13 110.9(4) . . ? N3 C14 C28 125.2(4) . . ? C13 C14 C28 123.9(4) . . ? C17 C16 C2 113.5(4) . . ? C3 C18 C19 113.3(4) . . ? C21 C20 C7 113.1(5) . . ? C23 C22 C8 105.9(8) . . ? C12 C24 C25 114.2(5) . . ? C13 C26 C27 112.6(5) . . ? 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 Pd N1 C1 166.4(4) . . . . ? N3 Pd N1 C1 66.8(9) . . . . ? Br Pd N1 C1 -45.6(4) . . . . ? N2 Pd N1 C4 -18.9(3) . . . . ? N3 Pd N1 C4 -118.5(7) . . . . ? Br Pd N1 C4 129.2(3) . . . . ? N1 Pd N2 C9 174.1(4) . . . . ? N3 Pd N2 C9 -16.5(4) . . . . ? Br Pd N2 C9 80.1(4) . . . . ? N1 Pd N2 C6 19.8(4) . . . . ? N3 Pd N2 C6 -170.8(4) . . . . ? Br Pd N2 C6 -74.1(4) . . . . ? N2 Pd N3 C14 -165.8(4) . . . . ? N1 Pd N3 C14 -66.3(9) . . . . ? Br Pd N3 C14 46.0(4) . . . . ? N2 Pd N3 C11 13.9(4) . . . . ? N1 Pd N3 C11 113.4(7) . . . . ? Br Pd N3 C11 -134.3(4) . . . . ? C4 N1 C1 C2 -3.7(5) . . . . ? Pd N1 C1 C2 171.8(3) . . . . ? C4 N1 C1 C15 175.2(4) . . . . ? Pd N1 C1 C15 -9.4(6) . . . . ? N1 C1 C2 C3 2.2(5) . . . . ? C15 C1 C2 C3 -176.7(4) . . . . ? N1 C1 C2 C16 -177.7(4) . . . . ? C15 C1 C2 C16 3.4(7) . . . . ? C1 C2 C3 C4 0.2(5) . . . . ? C16 C2 C3 C4 -179.8(4) . . . . ? C1 C2 C3 C18 179.7(4) . . . . ? C16 C2 C3 C18 -0.4(8) . . . . ? C1 N1 C4 C5 -171.7(4) . . . . ? Pd N1 C4 C5 12.6(6) . . . . ? C1 N1 C4 C3 3.8(5) . . . . ? Pd N1 C4 C3 -171.9(3) . . . . ? C2 C3 C4 C5 173.0(4) . . . . ? C18 C3 C4 C5 -6.5(7) . . . . ? C2 C3 C4 N1 -2.4(5) . . . . ? C18 C3 C4 N1 178.1(4) . . . . ? N1 C4 C5 C6 0.8(7) . . . . ? C3 C4 C5 C6 -173.9(4) . . . . ? C9 N2 C6 C5 -172.7(4) . . . . ? Pd N2 C6 C5 -14.5(6) . . . . ? C9 N2 C6 C7 2.6(5) . . . . ? Pd N2 C6 C7 160.8(3) . . . . ? C4 C5 C6 N2 0.2(7) . . . . ? C4 C5 C6 C7 -174.4(5) . . . . ? N2 C6 C7 C8 -1.8(6) . . . . ? C5 C6 C7 C8 173.5(5) . . . . ? N2 C6 C7 C20 177.2(5) . . . . ? C5 C6 C7 C20 -7.6(8) . . . . ? C6 C7 C8 C9 0.2(7) . . . . ? C20 C7 C8 C9 -178.7(6) . . . . ? C6 C7 C8 C22 -170.9(7) . . . . ? C20 C7 C8 C22 10.2(12) . . . . ? C6 N2 C9 C10 172.6(5) . . . . ? Pd N2 C9 C10 14.4(8) . . . . ? C6 N2 C9 C8 -2.4(6) . . . . ? Pd N2 C9 C8 -160.6(4) . . . . ? C7 C8 C9 N2 1.4(8) . . . . ? C22 C8 C9 N2 172.3(7) . . . . ? C7 C8 C9 C10 -173.5(6) . . . . ? C22 C8 C9 C10 -2.5(12) . . . . ? N2 C9 C10 C11 -3.9(11) . . . . ? C8 C9 C10 C11 170.3(7) . . . . ? C9 C10 C11 N3 1.1(10) . . . . ? C9 C10 C11 C12 174.3(6) . . . . ? C14 N3 C11 C10 170.6(5) . . . . ? Pd N3 C11 C10 -9.2(7) . . . . ? C14 N3 C11 C12 -3.8(5) . . . . ? Pd N3 C11 C12 176.5(3) . . . . ? C10 C11 C12 C13 -172.2(6) . . . . ? N3 C11 C12 C13 1.8(6) . . . . ? C10 C11 C12 C24 9.2(9) . . . . ? N3 C11 C12 C24 -176.7(5) . . . . ? C11 C12 C13 C14 0.6(6) . . . . ? C24 C12 C13 C14 179.1(5) . . . . ? C11 C12 C13 C26 -179.3(5) . . . . ? C24 C12 C13 C26 -0.9(9) . . . . ? C11 N3 C14 C13 4.2(5) . . . . ? Pd N3 C14 C13 -176.0(3) . . . . ? C11 N3 C14 C28 -172.6(5) . . . . ? Pd N3 C14 C28 7.2(7) . . . . ? C12 C13 C14 N3 -3.1(6) . . . . ? C26 C13 C14 N3 176.8(5) . . . . ? C12 C13 C14 C28 173.7(5) . . . . ? C26 C13 C14 C28 -6.3(8) . . . . ? C3 C2 C16 C17 88.7(6) . . . . ? C1 C2 C16 C17 -91.4(6) . . . . ? C2 C3 C18 C19 -99.0(6) . . . . ? C4 C3 C18 C19 80.3(6) . . . . ? C8 C7 C20 C21 87.1(8) . . . . ? C6 C7 C20 C21 -91.6(7) . . . . ? C7 C8 C22 C23 -108.6(9) . . . . ? C9 C8 C22 C23 82.1(10) . . . . ? C13 C12 C24 C25 -97.9(7) . . . . ? C11 C12 C24 C25 80.3(7) . . . . ? C12 C13 C26 C27 101.2(7) . . . . ? C14 C13 C26 C27 -78.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.061 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.102 #===END data_cb4cb _database_code_CSD 172680 _publ_section_exptl_prep ; Crystals were grown by slow concentration from a solution in dichloromethane layered with hexane at room temperature. ; _publ_section_exptl_refinement ; The CF3 group was found rotation disordered. Two independent positions were refined with occupancy factors 45 : 55. All fluorine atoms were refined with restraints to have the same U(ij) components (SIMU) and to have the same components of the anisotropic displacement parameters in the direction of the bond (DELU). ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '218 (dec.)' _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 F3 N3 O2 Pd' _chemical_formula_weight 579.93 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 monoclinic _symmetry_space_group_name_H-M 'P 1 2(1)/c 1' _symmetry_Int_Tables_number 14 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 12.6243(14) _cell_length_b 18.028(2) _cell_length_c 11.4931(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.859(2) _cell_angle_gamma 90.00 _cell_volume 2528.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7873 _cell_measurement_theta_min 2.375 _cell_measurement_theta_max 28.092 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.784 _exptl_absorpt_correction_type sadabs2 _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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_type 'Bruker Smart Apex with D8-Goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4450 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4450 _reflns_number_gt 3792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Smart 5.620' _computing_cell_refinement 'Smart 5.620' _computing_data_reduction 'Saint Plus' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP' _computing_publication_material 'XP' _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^)+(0.0496P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary Patterson _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 4450 _refine_ls_number_parameters 349 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0332 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0731 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.002 _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 Pd Pd 0.719372(14) 0.383253(10) 0.623368(15) 0.03386(9) Uani 1 1 d . . . N1 N 0.86527(16) 0.40903(12) 0.74191(17) 0.0394(5) Uani 1 1 d . . . N2 N 0.64200(15) 0.41916(11) 0.74145(16) 0.0372(4) Uani 1 1 d . . . N3 N 0.57317(15) 0.35349(11) 0.51397(17) 0.0369(4) Uani 1 1 d . . . F1 F 0.9022(6) 0.2970(5) 0.3473(8) 0.099(2) Uani 0.45 1 d PU A 1 F2 F 0.7591(10) 0.3248(5) 0.2121(9) 0.108(2) Uani 0.45 1 d PU A 1 F3 F 0.8885(10) 0.3985(7) 0.2609(10) 0.091(3) Uani 0.45 1 d PU A 1 F1' F 0.8460(5) 0.2800(4) 0.3170(6) 0.0919(18) Uani 0.55 1 d PU A 2 F2' F 0.7598(8) 0.3612(4) 0.1976(6) 0.102(2) Uani 0.55 1 d PU A 2 F3' F 0.9210(7) 0.3851(6) 0.3003(8) 0.101(3) Uani 0.55 1 d PU A 2 O1 O 0.79407(13) 0.34898(10) 0.49488(14) 0.0425(4) Uani 1 1 d . . . O2 O 0.74023(18) 0.44772(13) 0.37634(18) 0.0719(6) Uani 1 1 d . . . C1 C 0.9913(2) 0.43315(19) 0.6108(2) 0.0603(8) Uani 1 1 d . . . H1A H 0.9994 0.3874 0.5713 0.090 Uiso 1 1 calc R . . H1B H 1.0582 0.4610 0.6248 0.090 Uiso 1 1 calc R . . H1C H 0.9326 0.4614 0.5608 0.090 Uiso 1 1 calc R . . C2 C 0.9663(2) 0.41720(15) 0.7272(2) 0.0456(6) Uani 1 1 d . . . C3 C 1.0477(2) 0.41351(16) 0.8409(2) 0.0502(6) Uani 1 1 d . . . C4 C 0.9938(2) 0.40179(15) 0.9269(2) 0.0483(6) Uani 1 1 d . . . C5 C 0.8779(2) 0.40291(14) 0.8673(2) 0.0411(6) Uani 1 1 d . . . C6 C 0.7950(2) 0.41386(14) 0.9198(2) 0.0438(6) Uani 1 1 d . . . H6 H 0.8125 0.4110 1.0034 0.053 Uiso 1 1 calc R . . C7 C 0.6849(2) 0.42913(14) 0.8613(2) 0.0418(6) Uani 1 1 d . . . C8 C 0.6041(2) 0.46112(16) 0.9109(2) 0.0561(8) Uani 1 1 d . . . H8 H 0.6113 0.4723 0.9915 0.067 Uiso 1 1 calc R . . C9 C 0.5134(2) 0.47251(15) 0.8179(3) 0.0553(7) Uani 1 1 d . . . H9 H 0.4481 0.4944 0.8231 0.066 Uiso 1 1 calc R . . C10 C 0.5371(2) 0.44506(13) 0.7134(2) 0.0425(6) Uani 1 1 d . . . C11 C 0.4625(2) 0.43807(13) 0.5980(2) 0.0430(6) Uani 1 1 d . . . H11 H 0.3975 0.4648 0.5848 0.052 Uiso 1 1 calc R . . C12 C 0.4771(2) 0.39637(13) 0.5058(2) 0.0395(6) Uani 1 1 d . . . C13 C 0.3968(2) 0.37601(13) 0.3978(2) 0.0433(6) Uani 1 1 d . . . C14 C 0.4408(2) 0.32050(14) 0.3450(2) 0.0432(6) Uani 1 1 d . . . C15 C 0.5492(2) 0.30684(13) 0.4216(2) 0.0407(6) Uani 1 1 d . . . C16 C 0.6176(2) 0.24256(15) 0.4074(3) 0.0548(7) Uani 1 1 d . . . H16A H 0.6824 0.2415 0.4731 0.082 Uiso 1 1 calc R . . H16B H 0.6381 0.2469 0.3329 0.082 Uiso 1 1 calc R . . H16C H 0.5768 0.1976 0.4072 0.082 Uiso 1 1 calc R . . C17 C 1.1702(2) 0.42258(17) 0.8560(3) 0.0603(8) Uani 1 1 d . . . H17A H 1.1827 0.4651 0.8095 0.072 Uiso 1 1 calc R . . H17B H 1.2055 0.4324 0.9400 0.072 Uiso 1 1 calc R . . C18 C 1.2209(3) 0.3565(2) 0.8169(4) 0.0949(12) Uani 1 1 d . . . H18A H 1.2048 0.3136 0.8589 0.142 Uiso 1 1 calc R . . H18B H 1.2988 0.3632 0.8346 0.142 Uiso 1 1 calc R . . H18C H 1.1920 0.3496 0.7319 0.142 Uiso 1 1 calc R . . C19 C 1.0397(3) 0.38902(16) 1.0591(3) 0.0600(8) Uani 1 1 d . . . H19A H 0.9967 0.4166 1.1033 0.072 Uiso 1 1 calc R . . H19B H 1.1143 0.4076 1.0830 0.072 Uiso 1 1 calc R . . C20 C 1.0393(3) 0.3080(2) 1.0916(3) 0.0862(11) Uani 1 1 d . . . H20A H 0.9663 0.2887 1.0640 0.129 Uiso 1 1 calc R . . H20B H 1.0641 0.3025 1.1774 0.129 Uiso 1 1 calc R . . H20C H 1.0874 0.2812 1.0540 0.129 Uiso 1 1 calc R . . C21 C 0.2833(2) 0.40799(19) 0.3609(3) 0.0580(8) Uani 1 1 d . . . H21A H 0.2549 0.4024 0.2746 0.070 Uiso 1 1 calc R . . H21B H 0.2870 0.4606 0.3790 0.070 Uiso 1 1 calc R . . C22 C 0.2052(3) 0.3717(2) 0.4230(4) 0.0789(11) Uani 1 1 d . . . H22A H 0.1991 0.3198 0.4032 0.118 Uiso 1 1 calc R . . H22B H 0.1345 0.3946 0.3970 0.118 Uiso 1 1 calc R . . H22C H 0.2324 0.3773 0.5086 0.118 Uiso 1 1 calc R . . C23 C 0.3938(2) 0.28048(17) 0.2296(2) 0.0593(7) Uani 1 1 d . . . H23A H 0.3145 0.2844 0.2098 0.071 Uiso 1 1 calc R . . H23B H 0.4126 0.2283 0.2406 0.071 Uiso 1 1 calc R . . C24 C 0.4339(3) 0.3100(2) 0.1257(3) 0.0855(11) Uani 1 1 d . . . H24A H 0.4130 0.3611 0.1121 0.128 Uiso 1 1 calc R . . H24B H 0.4020 0.2817 0.0546 0.128 Uiso 1 1 calc R . . H24C H 0.5123 0.3060 0.1443 0.128 Uiso 1 1 calc R . . C25 C 0.7811(2) 0.38772(16) 0.4007(2) 0.0453(7) Uani 1 1 d . A . C26 C 0.8299(3) 0.3510(2) 0.3051(3) 0.0617(8) 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 Pd 0.03624(13) 0.03868(13) 0.02958(12) -0.00048(7) 0.01376(8) 0.00334(7) N1 0.0407(12) 0.0480(11) 0.0323(10) 0.0021(9) 0.0145(9) -0.0005(9) N2 0.0430(12) 0.0371(11) 0.0368(11) -0.0052(9) 0.0202(9) -0.0015(9) N3 0.0380(11) 0.0373(10) 0.0376(11) -0.0015(9) 0.0138(9) 0.0034(9) F1 0.120(5) 0.115(5) 0.081(4) 0.009(4) 0.058(4) 0.062(4) F2 0.120(4) 0.127(5) 0.075(4) -0.047(4) 0.024(3) -0.015(5) F3 0.106(7) 0.101(4) 0.092(6) 0.012(4) 0.072(5) 0.005(4) F1' 0.135(5) 0.078(3) 0.085(4) -0.015(2) 0.069(4) 0.013(3) F2' 0.135(4) 0.131(5) 0.038(2) -0.007(3) 0.018(2) 0.015(5) F3' 0.071(4) 0.139(6) 0.115(6) -0.032(5) 0.062(4) -0.014(4) O1 0.0419(10) 0.0551(11) 0.0344(9) -0.0020(8) 0.0171(7) 0.0081(8) O2 0.0847(15) 0.0767(15) 0.0643(14) 0.0214(11) 0.0370(11) 0.0324(13) C1 0.0453(16) 0.092(2) 0.0464(16) 0.0085(15) 0.0173(13) -0.0112(15) C2 0.0459(16) 0.0522(15) 0.0407(14) 0.0018(12) 0.0144(12) 0.0004(12) C3 0.0467(16) 0.0587(16) 0.0427(15) -0.0036(13) 0.0070(12) 0.0016(13) C4 0.0552(17) 0.0509(15) 0.0374(14) -0.0013(12) 0.0090(13) -0.0014(12) C5 0.0492(15) 0.0440(14) 0.0302(12) -0.0007(10) 0.0105(11) -0.0054(11) C6 0.0591(17) 0.0460(14) 0.0297(12) -0.0034(11) 0.0174(12) -0.0083(13) C7 0.0501(15) 0.0435(14) 0.0370(13) -0.0068(11) 0.0207(12) -0.0085(12) C8 0.0634(19) 0.0687(19) 0.0464(16) -0.0211(14) 0.0327(15) -0.0114(15) C9 0.0533(17) 0.0596(17) 0.0624(18) -0.0218(14) 0.0322(15) -0.0031(13) C10 0.0461(15) 0.0386(13) 0.0501(15) -0.0061(11) 0.0253(12) -0.0021(11) C11 0.0412(14) 0.0393(13) 0.0533(15) -0.0002(11) 0.0211(12) 0.0039(11) C12 0.0387(14) 0.0372(13) 0.0462(15) 0.0033(10) 0.0176(12) 0.0032(10) C13 0.0413(15) 0.0450(15) 0.0442(15) 0.0061(11) 0.0124(12) -0.0003(11) C14 0.0423(14) 0.0476(14) 0.0403(13) -0.0009(11) 0.0116(11) -0.0057(11) C15 0.0442(14) 0.0401(13) 0.0419(14) -0.0018(11) 0.0184(11) -0.0007(11) C16 0.0554(17) 0.0469(16) 0.0634(18) -0.0144(13) 0.0175(14) 0.0042(13) C17 0.0511(17) 0.0676(19) 0.0588(18) -0.0033(15) 0.0077(14) -0.0033(15) C18 0.072(2) 0.101(3) 0.106(3) -0.028(3) 0.014(2) 0.017(2) C19 0.0570(19) 0.081(2) 0.0365(15) 0.0003(13) 0.0022(13) -0.0002(15) C20 0.103(3) 0.098(3) 0.0500(19) 0.0136(18) 0.0053(18) 0.021(2) C21 0.0460(17) 0.0580(18) 0.066(2) 0.0026(15) 0.0067(15) 0.0050(13) C22 0.0464(19) 0.093(3) 0.100(3) -0.014(2) 0.0235(19) -0.0001(17) C23 0.0528(17) 0.0653(18) 0.0548(17) -0.0122(14) 0.0048(14) -0.0064(14) C24 0.101(3) 0.111(3) 0.0446(18) -0.0176(18) 0.0180(18) -0.013(2) C25 0.0374(15) 0.0646(19) 0.0364(14) -0.0019(12) 0.0138(12) 0.0053(12) C26 0.070(2) 0.078(2) 0.0426(17) -0.0042(16) 0.0247(16) -0.0006(19) _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 Pd N2 1.9735(18) . ? Pd N3 2.0212(19) . ? Pd O1 2.0411(15) . ? Pd N1 2.044(2) . ? N1 C2 1.337(3) . ? N1 C5 1.413(3) . ? N2 C7 1.357(3) . ? N2 C10 1.363(3) . ? N3 C15 1.327(3) . ? N3 C12 1.421(3) . ? F1 C26 1.337(9) . ? F2 C26 1.294(10) . ? F3 C26 1.315(13) . ? F1' C26 1.298(7) . ? F2' C26 1.336(8) . ? F3' C26 1.318(10) . ? O1 C25 1.263(3) . ? O2 C25 1.200(3) . ? C1 C2 1.479(3) . ? C2 C3 1.443(4) . ? C3 C4 1.353(4) . ? C3 C17 1.521(4) . ? C4 C5 1.448(4) . ? C4 C19 1.499(4) . ? C5 C6 1.350(3) . ? C6 C7 1.407(4) . ? C7 C8 1.413(3) . ? C8 C9 1.366(4) . ? C9 C10 1.400(3) . ? C10 C11 1.422(4) . ? C11 C12 1.350(3) . ? C12 C13 1.434(4) . ? C13 C14 1.361(3) . ? C13 C21 1.501(4) . ? C14 C15 1.446(3) . ? C14 C23 1.492(3) . ? C15 C16 1.479(3) . ? C17 C18 1.476(4) . ? C19 C20 1.508(4) . ? C21 C22 1.506(4) . ? C23 C24 1.509(4) . ? C25 C26 1.540(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 Pd N3 88.90(8) . . ? N2 Pd O1 177.19(7) . . ? N3 Pd O1 89.27(7) . . ? N2 Pd N1 89.28(8) . . ? N3 Pd N1 176.44(7) . . ? O1 Pd N1 92.67(7) . . ? C2 N1 C5 106.0(2) . . ? C2 N1 Pd 131.78(16) . . ? C5 N1 Pd 120.59(16) . . ? C7 N2 C10 107.79(19) . . ? C7 N2 Pd 127.03(17) . . ? C10 N2 Pd 124.92(16) . . ? C15 N3 C12 106.0(2) . . ? C15 N3 Pd 130.57(16) . . ? C12 N3 Pd 121.64(16) . . ? C25 O1 Pd 118.05(16) . . ? N1 C2 C3 111.2(2) . . ? N1 C2 C1 124.6(2) . . ? C3 C2 C1 124.1(2) . . ? C4 C3 C2 107.1(2) . . ? C4 C3 C17 128.4(3) . . ? C2 C3 C17 124.5(2) . . ? C3 C4 C5 106.8(2) . . ? C3 C4 C19 128.9(3) . . ? C5 C4 C19 124.3(2) . . ? C6 C5 N1 123.2(2) . . ? C6 C5 C4 126.5(2) . . ? N1 C5 C4 108.7(2) . . ? C5 C6 C7 126.8(2) . . ? N2 C7 C6 123.2(2) . . ? N2 C7 C8 108.8(2) . . ? C6 C7 C8 127.9(2) . . ? C9 C8 C7 107.0(2) . . ? C8 C9 C10 107.3(2) . . ? N2 C10 C9 109.1(2) . . ? N2 C10 C11 124.1(2) . . ? C9 C10 C11 126.5(2) . . ? C12 C11 C10 126.2(2) . . ? C11 C12 N3 122.5(2) . . ? C11 C12 C13 127.8(2) . . ? N3 C12 C13 108.7(2) . . ? C14 C13 C12 107.2(2) . . ? C14 C13 C21 128.7(3) . . ? C12 C13 C21 123.9(2) . . ? C13 C14 C15 106.5(2) . . ? C13 C14 C23 129.6(2) . . ? C15 C14 C23 123.9(2) . . ? N3 C15 C14 111.4(2) . . ? N3 C15 C16 124.4(2) . . ? C14 C15 C16 123.7(2) . . ? C18 C17 C3 112.7(3) . . ? C4 C19 C20 112.0(2) . . ? C13 C21 C22 113.1(3) . . ? C14 C23 C24 113.3(2) . . ? O2 C25 O1 130.7(3) . . ? O2 C25 C26 116.6(3) . . ? O1 C25 C26 112.7(2) . . ? F2 C26 F1' 77.5(5) . . ? F2 C26 F3 104.8(7) . . ? F1' C26 F3 126.4(7) . . ? F2 C26 F3' 124.1(7) . . ? F1' C26 F3' 110.5(6) . . ? F3 C26 F3' 25.5(6) . . ? F2 C26 F2' 29.8(5) . . ? F1' C26 F2' 106.4(5) . . ? F3 C26 F2' 81.9(6) . . ? F3' C26 F2' 106.0(6) . . ? F2 C26 F1 107.2(6) . . ? F1' C26 F1 33.9(4) . . ? F3 C26 F1 102.4(6) . . ? F3' C26 F1 80.4(6) . . ? F2' C26 F1 131.6(6) . . ? F2 C26 C25 115.4(6) . . ? F1' C26 C25 115.4(4) . . ? F3 C26 C25 111.3(7) . . ? F3' C26 C25 110.0(5) . . ? F2' C26 C25 108.0(5) . . ? F1 C26 C25 114.5(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 Pd N1 C2 -163.8(2) . . . . ? N3 Pd N1 C2 137.1(11) . . . . ? O1 Pd N1 C2 14.2(2) . . . . ? N2 Pd N1 C5 32.87(19) . . . . ? N3 Pd N1 C5 -26.3(13) . . . . ? O1 Pd N1 C5 -149.15(19) . . . . ? N3 Pd N2 C7 158.3(2) . . . . ? O1 Pd N2 C7 -152.4(14) . . . . ? N1 Pd N2 C7 -18.6(2) . . . . ? N3 Pd N2 C10 -28.27(19) . . . . ? O1 Pd N2 C10 21.0(16) . . . . ? N1 Pd N2 C10 154.78(19) . . . . ? N2 Pd N3 C15 -161.2(2) . . . . ? O1 Pd N3 C15 20.9(2) . . . . ? N1 Pd N3 C15 -102.0(12) . . . . ? N2 Pd N3 C12 36.14(18) . . . . ? O1 Pd N3 C12 -141.74(18) . . . . ? N1 Pd N3 C12 95.3(12) . . . . ? N2 Pd O1 C25 22.4(16) . . . . ? N3 Pd O1 C25 71.67(19) . . . . ? N1 Pd O1 C25 -111.32(19) . . . . ? C5 N1 C2 C3 2.5(3) . . . . ? Pd N1 C2 C3 -162.69(19) . . . . ? C5 N1 C2 C1 -173.6(3) . . . . ? Pd N1 C2 C1 21.3(4) . . . . ? N1 C2 C3 C4 0.8(3) . . . . ? C1 C2 C3 C4 176.8(3) . . . . ? N1 C2 C3 C17 -178.5(3) . . . . ? C1 C2 C3 C17 -2.4(5) . . . . ? C2 C3 C4 C5 -3.6(3) . . . . ? C17 C3 C4 C5 175.6(3) . . . . ? C2 C3 C4 C19 175.9(3) . . . . ? C17 C3 C4 C19 -4.9(5) . . . . ? C2 N1 C5 C6 161.6(3) . . . . ? Pd N1 C5 C6 -31.2(3) . . . . ? C2 N1 C5 C4 -4.6(3) . . . . ? Pd N1 C5 C4 162.54(17) . . . . ? C3 C4 C5 C6 -160.5(3) . . . . ? C19 C4 C5 C6 20.0(4) . . . . ? C3 C4 C5 N1 5.2(3) . . . . ? C19 C4 C5 N1 -174.3(2) . . . . ? N1 C5 C6 C7 3.2(4) . . . . ? C4 C5 C6 C7 166.9(3) . . . . ? C10 N2 C7 C6 -174.9(2) . . . . ? Pd N2 C7 C6 -0.6(4) . . . . ? C10 N2 C7 C8 1.0(3) . . . . ? Pd N2 C7 C8 175.35(17) . . . . ? C5 C6 C7 N2 14.9(4) . . . . ? C5 C6 C7 C8 -160.3(3) . . . . ? N2 C7 C8 C9 -2.1(3) . . . . ? C6 C7 C8 C9 173.6(3) . . . . ? C7 C8 C9 C10 2.3(3) . . . . ? C7 N2 C10 C9 0.4(3) . . . . ? Pd N2 C10 C9 -174.08(17) . . . . ? C7 N2 C10 C11 -174.2(2) . . . . ? Pd N2 C10 C11 11.3(3) . . . . ? C8 C9 C10 N2 -1.7(3) . . . . ? C8 C9 C10 C11 172.7(3) . . . . ? N2 C10 C11 C12 10.5(4) . . . . ? C9 C10 C11 C12 -163.2(3) . . . . ? C10 C11 C12 N3 -0.5(4) . . . . ? C10 C11 C12 C13 166.5(2) . . . . ? C15 N3 C12 C11 165.1(2) . . . . ? Pd N3 C12 C11 -28.5(3) . . . . ? C15 N3 C12 C13 -4.1(3) . . . . ? Pd N3 C12 C13 162.29(16) . . . . ? C11 C12 C13 C14 -166.0(3) . . . . ? N3 C12 C13 C14 2.5(3) . . . . ? C11 C12 C13 C21 9.4(4) . . . . ? N3 C12 C13 C21 177.9(2) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C21 C13 C14 C15 -175.1(3) . . . . ? C12 C13 C14 C23 -178.2(3) . . . . ? C21 C13 C14 C23 6.7(5) . . . . ? C12 N3 C15 C14 4.2(3) . . . . ? Pd N3 C15 C14 -160.55(16) . . . . ? C12 N3 C15 C16 -168.0(2) . . . . ? Pd N3 C15 C16 27.3(4) . . . . ? C13 C14 C15 N3 -2.7(3) . . . . ? C23 C14 C15 N3 175.6(2) . . . . ? C13 C14 C15 C16 169.5(2) . . . . ? C23 C14 C15 C16 -12.2(4) . . . . ? C4 C3 C17 C18 105.6(4) . . . . ? C2 C3 C17 C18 -75.3(4) . . . . ? C3 C4 C19 C20 -100.4(4) . . . . ? C5 C4 C19 C20 78.9(4) . . . . ? C14 C13 C21 C22 93.0(4) . . . . ? C12 C13 C21 C22 -81.4(4) . . . . ? C13 C14 C23 C24 98.1(4) . . . . ? C15 C14 C23 C24 -79.8(3) . . . . ? Pd O1 C25 O2 9.0(4) . . . . ? Pd O1 C25 C26 -173.13(18) . . . . ? O2 C25 C26 F2 -74.3(6) . . . . ? O1 C25 C26 F2 107.5(5) . . . . ? O2 C25 C26 F1' -161.9(4) . . . . ? O1 C25 C26 F1' 19.9(5) . . . . ? O2 C25 C26 F3 45.0(6) . . . . ? O1 C25 C26 F3 -133.2(5) . . . . ? O2 C25 C26 F3' 72.3(5) . . . . ? O1 C25 C26 F3' -106.0(5) . . . . ? O2 C25 C26 F2' -43.1(5) . . . . ? O1 C25 C26 F2' 138.7(4) . . . . ? O2 C25 C26 F1 160.6(5) . . . . ? O1 C25 C26 F1 -17.6(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.407 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.057 #===END data_sad _database_code_CSD 172681 _publ_section_exptl_prep ; Crystals were grown by slow concentration from a solution in dichloromethane layered with hexane at room temperature. ; _publ_section_exptl_refinement ; The CF3 group was found rotation disordered. Two independent positions were refined with occupancy factors 70 : 30. All fluorine atoms were refined with restraints to have the same U(ij) components (SIMU) and to have the same components of the anisotropic displacement parameters in the direction of the bond (DELU). ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '218 (dec.)' _chemical_formula_moiety ? _chemical_formula_sum 'C26 H30 F3 N3 O2 Pd' _chemical_formula_weight 579.93 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' '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' '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_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8220(7) _cell_length_b 11.3413(9) _cell_length_c 13.9761(11) _cell_angle_alpha 113.2790(10) _cell_angle_beta 100.8980(10) _cell_angle_gamma 93.0320(10) _cell_volume 1248.66(17) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7873 _cell_measurement_theta_min 2.375 _cell_measurement_theta_max 28.092 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_type sadabs2 _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 Smart Apex with D8-Goniometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24080 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _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 1.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4404 _reflns_number_gt 4268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Smart 5.620' _computing_cell_refinement 'Smart 5.620' _computing_data_reduction 'Saint Plus' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP' _computing_publication_material 'XP' _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^+1.0630P] 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 4404 _refine_ls_number_parameters 349 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0639 _refine_ls_wR_factor_gt 0.0634 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.098 _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 0.1730(3) 0.3078(2) 1.07480(19) 0.0330(5) Uani 1 1 d . . . H1A H 0.2618 0.3573 1.0682 0.050 Uiso 1 1 calc R . . H1B H 0.1677 0.3399 1.1501 0.050 Uiso 1 1 calc R . . H1C H 0.0764 0.3181 1.0327 0.050 Uiso 1 1 calc R . . C2 C 0.1926(3) 0.1674(2) 1.03412(18) 0.0247(5) Uani 1 1 d . . . C3 C 0.2623(3) 0.1083(2) 1.10348(18) 0.0260(5) Uani 1 1 d . . . C4 C 0.2487(3) -0.0215(2) 1.04071(19) 0.0258(5) Uani 1 1 d . . . C5 C 0.1727(3) -0.0406(2) 0.93338(18) 0.0240(5) Uani 1 1 d . . . C6 C 0.1268(3) -0.1562(2) 0.84700(19) 0.0263(5) Uani 1 1 d . . . H6 H 0.1548 -0.2304 0.8580 0.032 Uiso 1 1 calc R . . C7 C 0.0425(3) -0.1803(2) 0.74285(19) 0.0265(5) Uani 1 1 d . . . C8 C 0.0115(3) -0.3005(2) 0.6522(2) 0.0331(5) Uani 1 1 d . . . H8 H 0.0378 -0.3812 0.6509 0.040 Uiso 1 1 calc R . . C9 C -0.0634(3) -0.2788(2) 0.5668(2) 0.0330(5) Uani 1 1 d . . . H9 H -0.0987 -0.3416 0.4951 0.040 Uiso 1 1 calc R . . C10 C -0.0785(3) -0.1452(2) 0.60521(18) 0.0264(5) Uani 1 1 d . . . C11 C -0.1397(3) -0.0800(2) 0.54123(18) 0.0265(5) Uani 1 1 d . . . H11 H -0.1725 -0.1309 0.4664 0.032 Uiso 1 1 calc R . . C12 C -0.1562(3) 0.0478(2) 0.57607(18) 0.0253(5) Uani 1 1 d . . . C13 C -0.2343(3) 0.1133(2) 0.51478(19) 0.0291(5) Uani 1 1 d . . . C14 C -0.2461(3) 0.2345(3) 0.5865(2) 0.0347(6) Uani 1 1 d . . . C15 C -0.1747(3) 0.2426(2) 0.69184(19) 0.0315(5) Uani 1 1 d . . . C16 C -0.1802(4) 0.3532(3) 0.7942(2) 0.0448(7) Uani 1 1 d . . . H16A H -0.1420 0.3307 0.8544 0.067 Uiso 1 1 calc R . . H16B H -0.2879 0.3710 0.7928 0.067 Uiso 1 1 calc R . . H16C H -0.1143 0.4304 0.8022 0.067 Uiso 1 1 calc R . . C17 C 0.3354(3) 0.1803(2) 1.22101(19) 0.0300(5) Uani 1 1 d . . . H17A H 0.3455 0.1174 1.2540 0.036 Uiso 1 1 calc R . . H17B H 0.2654 0.2410 1.2551 0.036 Uiso 1 1 calc R . . C18 C 0.4963(3) 0.2567(3) 1.2438(2) 0.0421(6) Uani 1 1 d . . . H18A H 0.5673 0.1968 1.2123 0.063 Uiso 1 1 calc R . . H18B H 0.5373 0.3019 1.3213 0.063 Uiso 1 1 calc R . . H18C H 0.4870 0.3201 1.2124 0.063 Uiso 1 1 calc R . . C19 C 0.2997(3) -0.1270(2) 1.0734(2) 0.0287(5) Uani 1 1 d . . . H19A H 0.2269 -0.2080 1.0285 0.034 Uiso 1 1 calc R . . H19B H 0.2938 -0.1028 1.1487 0.034 Uiso 1 1 calc R . . C20 C 0.4656(3) -0.1521(3) 1.0627(2) 0.0394(6) Uani 1 1 d . . . H20A H 0.4715 -0.1792 0.9878 0.059 Uiso 1 1 calc R . . H20B H 0.4931 -0.2207 1.0860 0.059 Uiso 1 1 calc R . . H20C H 0.5385 -0.0725 1.1075 0.059 Uiso 1 1 calc R . . C21 C -0.2987(3) 0.0507(3) 0.39545(19) 0.0330(5) Uani 1 1 d . . . H21A H -0.2259 -0.0068 0.3611 0.040 Uiso 1 1 calc R . . H21B H -0.3061 0.1188 0.3679 0.040 Uiso 1 1 calc R . . C22 C -0.4591(3) -0.0283(3) 0.3650(2) 0.0412(6) Uani 1 1 d . . . H22A H -0.4530 -0.0944 0.3937 0.062 Uiso 1 1 calc R . . H22B H -0.4943 -0.0705 0.2869 0.062 Uiso 1 1 calc R . . H22C H -0.5333 0.0292 0.3948 0.062 Uiso 1 1 calc R . . C23 C -0.3148(4) 0.3446(3) 0.5661(2) 0.0512(8) Uani 1 1 d . . . H23A H -0.2594 0.4280 0.6235 0.061 Uiso 1 1 calc R . . H23B H -0.2958 0.3414 0.4975 0.061 Uiso 1 1 calc R . . C24 C -0.4853(4) 0.3417(4) 0.5614(3) 0.0681(10) Uani 1 1 d . . . H24A H -0.5422 0.2629 0.5009 0.102 Uiso 1 1 calc R . . H24B H -0.5198 0.4180 0.5522 0.102 Uiso 1 1 calc R . . H24C H -0.5059 0.3422 0.6280 0.102 Uiso 1 1 calc R . . C25 C 0.2109(3) 0.3266(2) 0.8124(2) 0.0327(5) Uani 1 1 d . A . C26 C 0.2773(4) 0.4725(3) 0.8643(3) 0.0503(7) Uani 1 1 d U . . F1 F 0.2493(9) 0.5382(8) 0.9579(6) 0.098(2) Uani 0.70 1 d PU A 1 F2 F 0.4315(7) 0.4927(9) 0.8710(6) 0.085(2) Uani 0.70 1 d PU A 1 F3 F 0.2141(9) 0.5297(7) 0.8019(5) 0.0969(19) Uani 0.70 1 d PU A 1 F1' F 0.3965(18) 0.494(2) 0.8380(14) 0.088(4) Uani 0.30 1 d PU A 2 F2' F 0.178(2) 0.5383(16) 0.8441(14) 0.108(4) Uani 0.30 1 d PU A 2 F3' F 0.314(2) 0.5180(18) 0.9715(12) 0.088(4) Uani 0.30 1 d PU A 2 N1 N 0.1439(2) 0.08073(18) 0.93311(15) 0.0233(4) Uani 1 1 d . . . N2 N -0.0170(2) -0.08672(17) 0.71368(15) 0.0237(4) Uani 1 1 d . . . N3 N -0.1154(2) 0.13447(18) 0.68464(15) 0.0252(4) Uani 1 1 d . . . O1 O 0.1279(2) 0.29619(15) 0.86622(13) 0.0303(4) Uani 1 1 d . . . O2 O 0.2444(3) 0.2621(2) 0.72920(17) 0.0553(6) Uani 1 1 d . . . Pd1 Pd 0.030543(18) 0.104650(15) 0.801054(13) 0.02171(7) Uani 1 1 d . A . 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 0.0454(15) 0.0262(12) 0.0254(12) 0.0088(10) 0.0067(11) 0.0081(11) C2 0.0247(11) 0.0254(11) 0.0244(11) 0.0098(9) 0.0076(9) 0.0032(9) C3 0.0238(11) 0.0299(12) 0.0269(12) 0.0138(10) 0.0071(9) 0.0035(9) C4 0.0220(11) 0.0292(12) 0.0289(12) 0.0139(10) 0.0076(9) 0.0033(9) C5 0.0220(11) 0.0246(11) 0.0293(12) 0.0138(10) 0.0084(9) 0.0055(9) C6 0.0250(11) 0.0237(11) 0.0340(13) 0.0147(10) 0.0089(10) 0.0051(9) C7 0.0265(12) 0.0216(11) 0.0315(12) 0.0104(10) 0.0081(10) 0.0044(9) C8 0.0397(14) 0.0210(12) 0.0356(14) 0.0085(10) 0.0087(11) 0.0066(10) C9 0.0366(14) 0.0240(12) 0.0298(13) 0.0030(10) 0.0059(11) 0.0052(10) C10 0.0242(11) 0.0254(12) 0.0263(12) 0.0069(10) 0.0067(9) 0.0020(9) C11 0.0240(11) 0.0289(12) 0.0225(11) 0.0067(10) 0.0053(9) 0.0020(9) C12 0.0223(11) 0.0293(12) 0.0243(11) 0.0098(10) 0.0081(9) 0.0044(9) C13 0.0285(12) 0.0344(13) 0.0270(12) 0.0143(10) 0.0082(10) 0.0056(10) C14 0.0408(14) 0.0356(14) 0.0302(13) 0.0155(11) 0.0075(11) 0.0123(11) C15 0.0366(13) 0.0282(12) 0.0277(12) 0.0096(10) 0.0056(10) 0.0092(10) C16 0.0620(19) 0.0365(15) 0.0313(14) 0.0089(12) 0.0067(13) 0.0252(13) C17 0.0345(13) 0.0322(13) 0.0252(12) 0.0134(10) 0.0080(10) 0.0050(10) C18 0.0396(15) 0.0509(17) 0.0297(14) 0.0149(12) 0.0009(11) -0.0046(13) C19 0.0306(12) 0.0283(12) 0.0306(12) 0.0162(10) 0.0057(10) 0.0043(10) C20 0.0400(15) 0.0464(16) 0.0427(15) 0.0254(13) 0.0160(12) 0.0175(12) C21 0.0374(14) 0.0402(14) 0.0250(12) 0.0164(11) 0.0078(10) 0.0091(11) C22 0.0345(14) 0.0584(18) 0.0273(13) 0.0163(13) 0.0027(11) 0.0058(13) C23 0.069(2) 0.0493(18) 0.0361(15) 0.0191(14) 0.0048(14) 0.0246(16) C24 0.068(2) 0.068(2) 0.085(3) 0.045(2) 0.020(2) 0.0283(19) C25 0.0392(14) 0.0262(12) 0.0311(13) 0.0112(11) 0.0064(11) 0.0028(10) C26 0.0701(19) 0.0299(14) 0.0533(17) 0.0163(13) 0.0234(15) 0.0006(13) F1 0.168(6) 0.028(2) 0.085(3) -0.009(2) 0.076(4) -0.017(3) F2 0.059(2) 0.059(3) 0.107(5) 0.012(3) 0.007(2) -0.0205(18) F3 0.142(4) 0.052(3) 0.114(4) 0.060(3) 0.011(3) 0.013(3) F1' 0.108(7) 0.058(5) 0.088(8) 0.017(6) 0.048(7) -0.043(7) F2' 0.136(7) 0.032(4) 0.145(9) 0.034(7) 0.009(7) 0.022(5) F3' 0.140(10) 0.049(8) 0.043(3) -0.003(4) 0.014(5) -0.046(7) N1 0.0225(9) 0.0222(9) 0.0261(10) 0.0105(8) 0.0063(8) 0.0037(7) N2 0.0231(9) 0.0214(9) 0.0249(10) 0.0080(8) 0.0052(8) 0.0023(7) N3 0.0273(10) 0.0240(10) 0.0233(10) 0.0087(8) 0.0055(8) 0.0062(8) O1 0.0410(10) 0.0212(8) 0.0264(8) 0.0083(7) 0.0073(7) 0.0009(7) O2 0.0752(15) 0.0381(11) 0.0465(12) 0.0038(9) 0.0339(11) -0.0042(10) Pd1 0.02418(11) 0.01894(10) 0.02128(10) 0.00763(7) 0.00486(7) 0.00368(7) _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 C2 1.496(3) . ? C2 N1 1.332(3) . ? C2 C3 1.449(3) . ? C3 C4 1.368(3) . ? C3 C17 1.505(3) . ? C4 C5 1.447(3) . ? C4 C19 1.501(3) . ? C5 C6 1.360(3) . ? C5 N1 1.414(3) . ? C6 C7 1.415(3) . ? C7 N2 1.374(3) . ? C7 C8 1.416(3) . ? C8 C9 1.369(4) . ? C9 C10 1.417(3) . ? C10 N2 1.374(3) . ? C10 C11 1.421(3) . ? C11 C12 1.361(3) . ? C12 N3 1.405(3) . ? C12 C13 1.446(3) . ? C13 C14 1.367(4) . ? C13 C21 1.507(3) . ? C14 C15 1.452(3) . ? C14 C23 1.519(4) . ? C15 N3 1.334(3) . ? C15 C16 1.495(3) . ? C17 C18 1.532(4) . ? C19 C20 1.529(3) . ? C21 C22 1.525(4) . ? C23 C24 1.491(5) . ? C25 O2 1.207(3) . ? C25 O1 1.268(3) . ? C25 C26 1.547(4) . ? C26 F1' 1.221(15) . ? C26 F2' 1.242(17) . ? C26 F1 1.304(7) . ? C26 F3 1.338(7) . ? C26 F3' 1.343(15) . ? C26 F2 1.346(7) . ? N1 Pd1 2.0510(18) . ? N2 Pd1 1.9982(18) . ? N3 Pd1 2.0269(19) . ? O1 Pd1 2.0565(16) . ? 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 C2 C3 111.6(2) . . ? N1 C2 C1 125.5(2) . . ? C3 C2 C1 122.8(2) . . ? C4 C3 C2 106.5(2) . . ? C4 C3 C17 128.5(2) . . ? C2 C3 C17 125.0(2) . . ? C3 C4 C5 106.7(2) . . ? C3 C4 C19 128.2(2) . . ? C5 C4 C19 125.1(2) . . ? C6 C5 N1 124.5(2) . . ? C6 C5 C4 126.4(2) . . ? N1 C5 C4 109.04(19) . . ? C5 C6 C7 128.3(2) . . ? N2 C7 C6 124.2(2) . . ? N2 C7 C8 109.4(2) . . ? C6 C7 C8 126.4(2) . . ? C9 C8 C7 107.2(2) . . ? C8 C9 C10 107.2(2) . . ? N2 C10 C9 109.2(2) . . ? N2 C10 C11 125.1(2) . . ? C9 C10 C11 125.6(2) . . ? C12 C11 C10 126.8(2) . . ? C11 C12 N3 123.0(2) . . ? C11 C12 C13 127.8(2) . . ? N3 C12 C13 108.8(2) . . ? C14 C13 C12 106.8(2) . . ? C14 C13 C21 128.7(2) . . ? C12 C13 C21 124.3(2) . . ? C13 C14 C15 106.6(2) . . ? C13 C14 C23 129.2(2) . . ? C15 C14 C23 124.2(2) . . ? N3 C15 C14 110.9(2) . . ? N3 C15 C16 125.1(2) . . ? C14 C15 C16 123.9(2) . . ? C3 C17 C18 113.3(2) . . ? C4 C19 C20 113.0(2) . . ? C13 C21 C22 112.2(2) . . ? C24 C23 C14 114.2(3) . . ? O2 C25 O1 131.1(2) . . ? O2 C25 C26 116.2(2) . . ? O1 C25 C26 112.7(2) . . ? F1' C26 F2' 110.4(12) . . ? F1' C26 F1 124.0(10) . . ? F2' C26 F1 77.6(9) . . ? F1' C26 F3 83.7(10) . . ? F2' C26 F3 31.0(8) . . ? F1 C26 F3 105.7(5) . . ? F1' C26 F3' 106.2(11) . . ? F2' C26 F3' 105.0(11) . . ? F1 C26 F3' 28.4(8) . . ? F3 C26 F3' 129.5(9) . . ? F1' C26 F2 22.3(10) . . ? F2' C26 F2 126.8(9) . . ? F1 C26 F2 109.0(5) . . ? F3 C26 F2 104.2(5) . . ? F3' C26 F2 86.3(9) . . ? F1' C26 C25 112.6(10) . . ? F2' C26 C25 111.1(9) . . ? F1 C26 C25 115.0(4) . . ? F3 C26 C25 109.8(4) . . ? F3' C26 C25 111.1(9) . . ? F2 C26 C25 112.4(5) . . ? C2 N1 C5 106.09(19) . . ? C2 N1 Pd1 129.59(16) . . ? C5 N1 Pd1 124.10(15) . . ? C7 N2 C10 106.88(19) . . ? C7 N2 Pd1 125.97(15) . . ? C10 N2 Pd1 125.00(15) . . ? C15 N3 C12 106.80(19) . . ? C15 N3 Pd1 127.79(16) . . ? C12 N3 Pd1 124.93(15) . . ? C25 O1 Pd1 115.24(15) . . ? N2 Pd1 N3 90.08(8) . . ? N2 Pd1 N1 92.05(7) . . ? N3 Pd1 N1 169.15(7) . . ? N2 Pd1 O1 163.52(7) . . ? N3 Pd1 O1 89.44(7) . . ? N1 Pd1 O1 91.51(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 -2.3(3) . . . . ? C1 C2 C3 C4 175.0(2) . . . . ? N1 C2 C3 C17 177.0(2) . . . . ? C1 C2 C3 C17 -5.7(4) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C17 C3 C4 C5 -178.7(2) . . . . ? C2 C3 C4 C19 -178.9(2) . . . . ? C17 C3 C4 C19 1.8(4) . . . . ? C3 C4 C5 C6 -175.2(2) . . . . ? C19 C4 C5 C6 4.4(4) . . . . ? C3 C4 C5 N1 1.1(2) . . . . ? C19 C4 C5 N1 -179.4(2) . . . . ? N1 C5 C6 C7 -0.7(4) . . . . ? C4 C5 C6 C7 175.0(2) . . . . ? C5 C6 C7 N2 -4.5(4) . . . . ? C5 C6 C7 C8 172.7(2) . . . . ? N2 C7 C8 C9 1.7(3) . . . . ? C6 C7 C8 C9 -175.8(2) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C8 C9 C10 N2 -1.6(3) . . . . ? C8 C9 C10 C11 175.3(2) . . . . ? N2 C10 C11 C12 -4.0(4) . . . . ? C9 C10 C11 C12 179.6(2) . . . . ? C10 C11 C12 N3 -1.2(4) . . . . ? C10 C11 C12 C13 -172.2(2) . . . . ? C11 C12 C13 C14 169.2(2) . . . . ? N3 C12 C13 C14 -2.8(3) . . . . ? C11 C12 C13 C21 -6.6(4) . . . . ? N3 C12 C13 C21 -178.6(2) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C21 C13 C14 C15 175.6(2) . . . . ? C12 C13 C14 C23 178.7(3) . . . . ? C21 C13 C14 C23 -5.8(5) . . . . ? C13 C14 C15 N3 2.9(3) . . . . ? C23 C14 C15 N3 -175.8(3) . . . . ? C13 C14 C15 C16 -172.1(3) . . . . ? C23 C14 C15 C16 9.1(4) . . . . ? C4 C3 C17 C18 104.0(3) . . . . ? C2 C3 C17 C18 -75.2(3) . . . . ? C3 C4 C19 C20 -91.4(3) . . . . ? C5 C4 C19 C20 89.2(3) . . . . ? C14 C13 C21 C22 -92.8(3) . . . . ? C12 C13 C21 C22 82.0(3) . . . . ? C13 C14 C23 C24 88.3(4) . . . . ? C15 C14 C23 C24 -93.2(4) . . . . ? O2 C25 C26 F1' -25.4(10) . . . . ? O1 C25 C26 F1' 155.2(9) . . . . ? O2 C25 C26 F2' 99.1(9) . . . . ? O1 C25 C26 F2' -80.3(9) . . . . ? O2 C25 C26 F1 -175.1(5) . . . . ? O1 C25 C26 F1 5.5(5) . . . . ? O2 C25 C26 F3 65.9(5) . . . . ? O1 C25 C26 F3 -113.5(4) . . . . ? O2 C25 C26 F3' -144.4(8) . . . . ? O1 C25 C26 F3' 36.2(9) . . . . ? O2 C25 C26 F2 -49.6(5) . . . . ? O1 C25 C26 F2 131.0(4) . . . . ? C3 C2 N1 C5 2.9(2) . . . . ? C1 C2 N1 C5 -174.3(2) . . . . ? C3 C2 N1 Pd1 177.65(14) . . . . ? C1 C2 N1 Pd1 0.4(3) . . . . ? C6 C5 N1 C2 173.9(2) . . . . ? C4 C5 N1 C2 -2.5(2) . . . . ? C6 C5 N1 Pd1 -1.2(3) . . . . ? C4 C5 N1 Pd1 -177.55(14) . . . . ? C6 C7 N2 C10 174.9(2) . . . . ? C8 C7 N2 C10 -2.7(3) . . . . ? C6 C7 N2 Pd1 11.0(3) . . . . ? C8 C7 N2 Pd1 -166.58(16) . . . . ? C9 C10 N2 C7 2.6(3) . . . . ? C11 C10 N2 C7 -174.2(2) . . . . ? C9 C10 N2 Pd1 166.73(16) . . . . ? C11 C10 N2 Pd1 -10.2(3) . . . . ? C14 C15 N3 C12 -4.7(3) . . . . ? C16 C15 N3 C12 170.4(3) . . . . ? C14 C15 N3 Pd1 167.63(17) . . . . ? C16 C15 N3 Pd1 -17.3(4) . . . . ? C11 C12 N3 C15 -167.9(2) . . . . ? C13 C12 N3 C15 4.6(3) . . . . ? C11 C12 N3 Pd1 19.6(3) . . . . ? C13 C12 N3 Pd1 -167.94(15) . . . . ? O2 C25 O1 Pd1 -0.7(4) . . . . ? C26 C25 O1 Pd1 178.59(18) . . . . ? C7 N2 Pd1 N3 -179.21(18) . . . . ? C10 N2 Pd1 N3 19.71(18) . . . . ? C7 N2 Pd1 N1 -9.85(18) . . . . ? C10 N2 Pd1 N1 -170.93(18) . . . . ? C7 N2 Pd1 O1 92.5(3) . . . . ? C10 N2 Pd1 O1 -68.6(3) . . . . ? C15 N3 Pd1 N2 164.6(2) . . . . ? C12 N3 Pd1 N2 -24.41(18) . . . . ? C15 N3 Pd1 N1 63.2(5) . . . . ? C12 N3 Pd1 N1 -125.8(4) . . . . ? C15 N3 Pd1 O1 -31.9(2) . . . . ? C12 N3 Pd1 O1 139.11(18) . . . . ? C2 N1 Pd1 N2 -168.72(19) . . . . ? C5 N1 Pd1 N2 5.15(17) . . . . ? C2 N1 Pd1 N3 -67.5(4) . . . . ? C5 N1 Pd1 N3 106.4(4) . . . . ? C2 N1 Pd1 O1 27.38(19) . . . . ? C5 N1 Pd1 O1 -158.75(17) . . . . ? C25 O1 Pd1 N2 17.5(3) . . . . ? C25 O1 Pd1 N3 -70.87(18) . . . . ? C25 O1 Pd1 N1 119.94(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.006 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.063