# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Eric Ferreira' _publ_contact_author_email emferr@mail.colostate.edu loop_ _publ_author_name E.Stache C.Seizert E.Ferreira data_ef05 _database_code_depnum_ccdc_archive 'CCDC 839648' #TrackingRef '- nitrobenzoate.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 N4 O5' _chemical_formula_weight 500.54 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _chemical_absolute_configuration rm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5307(4) _cell_length_b 9.5523(5) _cell_length_c 30.0128(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2445.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 6423 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 21.79 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.383 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.065 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6607 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details 'SADABS, Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22831 _diffrn_reflns_av_R_equivalents 0.0767 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 20.82 _reflns_number_total 2574 _reflns_number_gt 2212 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0857P)^2^+0.2483P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_ls_number_reflns 2574 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3299(6) 0.1011(5) 0.35917(17) 0.0221(13) Uani 1 1 d . . . C2 C 0.2788(6) 0.2290(6) 0.34505(19) 0.0291(15) Uani 1 1 d . . . H2 H 0.2393 0.2939 0.3652 0.035 Uiso 1 1 calc R . . C3 C 0.3829(7) 0.0024(6) 0.33029(16) 0.0306(15) Uani 1 1 d . . . H3 H 0.4142 -0.0850 0.3407 0.037 Uiso 1 1 calc R . . C4 C 0.2870(6) 0.2603(6) 0.29993(19) 0.0289(15) Uani 1 1 d . . . H4 H 0.2548 0.3476 0.2897 0.035 Uiso 1 1 calc R . . C5 C 0.3898(7) 0.0326(5) 0.28579(16) 0.0262(14) Uani 1 1 d . . . H5 H 0.4263 -0.0343 0.2658 0.031 Uiso 1 1 calc R . . C6 C 0.3425(6) 0.1623(6) 0.27044(16) 0.0213(13) Uani 1 1 d . . . C7 C 0.3578(7) 0.2035(6) 0.22271(18) 0.0245(14) Uani 1 1 d . . . C8 C 0.4559(7) 0.1308(6) 0.15172(16) 0.0268(14) Uani 1 1 d . . . H8A H 0.5671 0.1515 0.1505 0.032 Uiso 1 1 calc R . . H8B H 0.3994 0.2130 0.1416 0.032 Uiso 1 1 calc R . . C9 C 0.4198(6) 0.0088(6) 0.12127(15) 0.0204(13) Uani 1 1 d . . . H9 H 0.4412 -0.0780 0.1376 0.024 Uiso 1 1 calc R . . C10 C 0.5283(6) 0.0141(6) 0.08072(16) 0.0334(15) Uani 1 1 d . . . H10A H 0.5170 0.1028 0.0660 0.050 Uiso 1 1 calc R . . H10B H 0.5011 -0.0598 0.0605 0.050 Uiso 1 1 calc R . . H10C H 0.6350 0.0025 0.0902 0.050 Uiso 1 1 calc R . . C11 C 0.2507(6) 0.0035(6) 0.10432(15) 0.0161(12) Uani 1 1 d . . . H11 H 0.2409 -0.0766 0.0841 0.019 Uiso 1 1 calc R . . C12 C 0.1390(6) -0.1218(5) 0.17186(16) 0.0179(13) Uani 1 1 d . . . C13 C 0.0985(6) -0.0952(5) 0.21582(16) 0.0230(14) Uani 1 1 d . . . H13 H 0.0603 -0.0078 0.2241 0.028 Uiso 1 1 calc R . . C14 C 0.1927(7) -0.2540(5) 0.15971(18) 0.0246(14) Uani 1 1 d . . . H14 H 0.2168 -0.2727 0.1301 0.030 Uiso 1 1 calc R . . C15 C 0.1156(7) -0.2005(6) 0.24740(18) 0.0309(15) Uani 1 1 d . . . H15 H 0.0890 -0.1840 0.2770 0.037 Uiso 1 1 calc R . . C16 C 0.2101(7) -0.3562(6) 0.19113(19) 0.0324(15) Uani 1 1 d . . . H16 H 0.2478 -0.4437 0.1828 0.039 Uiso 1 1 calc R . . C17 C 0.1729(6) -0.3311(6) 0.23454(19) 0.0298(15) Uani 1 1 d . . . H17 H 0.1857 -0.4014 0.2557 0.036 Uiso 1 1 calc R . . C18 C 0.0090(6) 0.0811(5) 0.13510(16) 0.0179(13) Uani 1 1 d . . . C19 C 0.0523(6) 0.1838(5) 0.09838(15) 0.0155(12) Uani 1 1 d . . . C20 C -0.0643(6) 0.1839(6) 0.05906(15) 0.0224(13) Uani 1 1 d . . . H20A H -0.1240 0.0975 0.0581 0.027 Uiso 1 1 calc R . . H20B H -0.1363 0.2623 0.0611 0.027 Uiso 1 1 calc R . . C21 C 0.0433(7) 0.1977(6) 0.01820(17) 0.0307(15) Uani 1 1 d . . . H21A H -0.0068 0.1613 -0.0084 0.037 Uiso 1 1 calc R . . H21B H 0.0732 0.2944 0.0132 0.037 Uiso 1 1 calc R . . C22 C 0.1830(6) 0.1097(5) 0.03128(15) 0.0224(14) Uani 1 1 d . . . H22A H 0.1642 0.0118 0.0246 0.027 Uiso 1 1 calc R . . H22B H 0.2761 0.1400 0.0154 0.027 Uiso 1 1 calc R . . C23 C 0.0664(6) 0.3306(5) 0.12030(15) 0.0182(13) Uani 1 1 d . . . H23A H -0.0339 0.3548 0.1334 0.022 Uiso 1 1 calc R . . H23B H 0.1426 0.3254 0.1442 0.022 Uiso 1 1 calc R . . C24 C 0.1143(6) 0.4460(5) 0.08895(15) 0.0176(13) Uani 1 1 d . . . C25 C 0.2673(6) 0.4635(6) 0.07488(16) 0.0228(14) Uani 1 1 d . . . H25 H 0.3458 0.4051 0.0857 0.027 Uiso 1 1 calc R . . C26 C 0.3030(7) 0.5670(5) 0.04492(17) 0.0265(14) Uani 1 1 d . . . H26 H 0.4053 0.5790 0.0349 0.032 Uiso 1 1 calc R . . C27 C 0.1843(7) 0.6531(6) 0.02990(16) 0.0254(14) Uani 1 1 d . . . H27 H 0.2039 0.7235 0.0092 0.031 Uiso 1 1 calc R . . C28 C 0.0383(7) 0.6317(6) 0.04625(17) 0.0294(14) Uani 1 1 d . . . H28 H -0.0405 0.6918 0.0366 0.035 Uiso 1 1 calc R . . N1 N 0.3346(5) 0.0714(6) 0.40688(15) 0.0274(12) Uani 1 1 d . . . N2 N 0.1317(5) -0.0111(4) 0.13976(12) 0.0166(10) Uani 1 1 d . . . N3 N 0.2020(5) 0.1311(4) 0.07996(13) 0.0184(11) Uani 1 1 d . . . N4 N -0.0017(5) 0.5314(5) 0.07507(14) 0.0269(12) Uani 1 1 d . . . O1 O 0.3222(5) 0.1696(4) 0.43316(12) 0.0348(11) Uani 1 1 d . . . O2 O 0.3580(4) -0.0500(5) 0.41876(11) 0.0313(10) Uani 1 1 d . . . O3 O 0.3270(5) 0.3183(4) 0.20856(13) 0.0380(11) Uani 1 1 d . . . O4 O 0.4112(4) 0.0991(4) 0.19732(11) 0.0273(10) Uani 1 1 d . . . O5 O -0.1121(4) 0.0801(3) 0.15672(11) 0.0246(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.016(3) 0.027(4) 0.024(3) 0.000(3) 0.000(3) -0.001(3) C2 0.025(4) 0.028(4) 0.034(4) -0.012(3) -0.004(3) 0.003(3) C3 0.042(4) 0.023(3) 0.027(4) 0.001(3) -0.003(3) 0.006(3) C4 0.026(4) 0.024(3) 0.037(4) 0.000(3) -0.011(3) 0.005(3) C5 0.039(4) 0.016(3) 0.023(3) 0.000(2) -0.004(3) 0.007(3) C6 0.015(3) 0.026(3) 0.023(3) -0.006(3) -0.011(2) 0.002(3) C7 0.022(4) 0.018(4) 0.033(4) -0.004(3) -0.006(3) -0.004(3) C8 0.018(3) 0.035(3) 0.028(3) 0.011(3) -0.001(3) -0.004(3) C9 0.017(3) 0.024(3) 0.021(3) 0.004(2) 0.005(2) 0.002(3) C10 0.019(3) 0.047(4) 0.034(3) 0.010(3) 0.005(3) 0.012(3) C11 0.020(3) 0.011(3) 0.017(3) 0.003(2) 0.009(2) 0.000(2) C12 0.014(3) 0.017(3) 0.023(3) 0.007(2) -0.003(2) -0.006(3) C13 0.020(3) 0.026(3) 0.023(3) -0.001(3) 0.007(2) 0.002(3) C14 0.035(4) 0.016(3) 0.022(3) 0.002(3) 0.001(3) -0.005(3) C15 0.032(4) 0.043(4) 0.018(3) 0.010(3) 0.000(3) -0.014(3) C16 0.043(4) 0.021(4) 0.033(4) 0.010(3) -0.007(3) -0.001(3) C17 0.025(4) 0.028(4) 0.037(4) 0.019(3) -0.006(3) -0.004(3) C18 0.020(3) 0.016(3) 0.017(3) 0.000(2) -0.001(3) -0.008(3) C19 0.013(3) 0.018(3) 0.015(3) 0.000(2) -0.001(2) 0.001(3) C20 0.025(4) 0.020(3) 0.022(3) 0.004(2) -0.002(3) -0.003(3) C21 0.034(4) 0.035(4) 0.023(3) -0.002(3) -0.006(3) 0.001(3) C22 0.028(3) 0.025(3) 0.014(3) 0.005(2) 0.001(2) -0.004(3) C23 0.017(3) 0.021(3) 0.017(3) 0.001(2) 0.003(2) 0.005(3) C24 0.021(3) 0.011(3) 0.022(3) -0.003(2) -0.002(3) 0.002(3) C25 0.023(4) 0.022(3) 0.023(3) 0.001(3) -0.001(3) 0.001(3) C26 0.025(3) 0.024(3) 0.030(3) -0.001(3) 0.005(3) -0.001(3) C27 0.032(4) 0.024(3) 0.020(3) 0.006(3) 0.003(3) -0.005(3) C28 0.031(4) 0.026(3) 0.031(3) 0.011(3) -0.004(3) 0.001(3) N1 0.021(3) 0.033(3) 0.029(3) -0.002(3) 0.002(2) -0.004(3) N2 0.016(3) 0.017(2) 0.018(2) 0.005(2) -0.001(2) 0.001(2) N3 0.015(3) 0.023(3) 0.017(2) 0.005(2) 0.0041(19) 0.003(2) N4 0.026(3) 0.023(3) 0.031(3) 0.006(2) 0.002(2) 0.002(3) O1 0.037(3) 0.039(3) 0.028(2) -0.013(2) -0.0014(18) -0.006(2) O2 0.031(2) 0.036(3) 0.027(2) 0.0028(19) -0.0025(18) 0.000(2) O3 0.056(3) 0.021(2) 0.037(2) 0.007(2) -0.004(2) 0.007(2) O4 0.033(3) 0.026(2) 0.022(2) 0.0069(18) -0.0023(18) 0.0014(19) O5 0.021(2) 0.025(2) 0.027(2) 0.0084(17) 0.0073(19) 0.0009(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 C1 C3 1.358(7) . ? C1 C2 1.365(7) . ? C1 N1 1.460(7) . ? C2 C4 1.388(8) . ? C3 C5 1.368(7) . ? C4 C6 1.373(7) . ? C5 C6 1.383(7) . ? C6 C7 1.491(7) . ? C7 O3 1.205(6) . ? C7 O4 1.336(6) . ? C8 O4 1.453(6) . ? C8 C9 1.512(7) . ? C9 C10 1.530(7) . ? C9 C11 1.530(7) . ? C11 N2 1.477(6) . ? C11 N3 1.481(6) . ? C12 C13 1.387(7) . ? C12 C14 1.392(7) . ? C12 N2 1.432(6) . ? C13 C15 1.390(7) . ? C14 C16 1.366(7) . ? C15 C17 1.394(8) . ? C16 C17 1.362(8) . ? C18 O5 1.220(6) . ? C18 N2 1.375(6) . ? C18 C19 1.522(7) . ? C19 N3 1.480(6) . ? C19 C20 1.544(7) . ? C19 C23 1.554(7) . ? C20 C21 1.538(7) . ? C21 C22 1.510(7) . ? C22 N3 1.484(6) . ? C23 C24 1.505(7) . ? C24 N4 1.349(6) . ? C24 C25 1.382(7) . ? C25 C26 1.371(7) . ? C26 C27 1.380(7) . ? C27 C28 1.354(8) . ? C28 N4 1.335(6) . ? N1 O2 1.230(5) . ? N1 O1 1.230(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 C2 122.0(5) . . ? C3 C1 N1 118.8(5) . . ? C2 C1 N1 119.1(5) . . ? C1 C2 C4 118.6(5) . . ? C1 C3 C5 119.4(5) . . ? C6 C4 C2 120.0(5) . . ? C3 C5 C6 120.1(5) . . ? C4 C6 C5 119.8(5) . . ? C4 C6 C7 118.0(5) . . ? C5 C6 C7 122.1(5) . . ? O3 C7 O4 123.6(5) . . ? O3 C7 C6 124.0(5) . . ? O4 C7 C6 112.4(5) . . ? O4 C8 C9 110.8(4) . . ? C8 C9 C10 109.4(4) . . ? C8 C9 C11 114.7(4) . . ? C10 C9 C11 107.9(4) . . ? N2 C11 N3 103.9(4) . . ? N2 C11 C9 114.3(4) . . ? N3 C11 C9 113.7(4) . . ? C13 C12 C14 119.8(4) . . ? C13 C12 N2 119.6(5) . . ? C14 C12 N2 120.5(4) . . ? C12 C13 C15 119.3(5) . . ? C16 C14 C12 120.2(5) . . ? C13 C15 C17 119.7(5) . . ? C17 C16 C14 120.6(6) . . ? C16 C17 C15 120.2(5) . . ? O5 C18 N2 125.9(4) . . ? O5 C18 C19 126.6(5) . . ? N2 C18 C19 107.5(4) . . ? N3 C19 C18 105.1(4) . . ? N3 C19 C20 105.7(4) . . ? C18 C19 C20 113.4(4) . . ? N3 C19 C23 113.5(4) . . ? C18 C19 C23 107.1(4) . . ? C20 C19 C23 111.9(4) . . ? C21 C20 C19 103.0(4) . . ? C22 C21 C20 102.5(4) . . ? N3 C22 C21 105.4(4) . . ? C24 C23 C19 114.7(4) . . ? N4 C24 C25 121.7(5) . . ? N4 C24 C23 115.9(4) . . ? C25 C24 C23 122.4(5) . . ? C26 C25 C24 119.8(5) . . ? C25 C26 C27 118.8(5) . . ? C28 C27 C26 117.8(5) . . ? N4 C28 C27 125.3(5) . . ? O2 N1 O1 123.2(4) . . ? O2 N1 C1 118.2(5) . . ? O1 N1 C1 118.6(5) . . ? C18 N2 C12 125.0(4) . . ? C18 N2 C11 113.0(4) . . ? C12 N2 C11 121.6(4) . . ? C19 N3 C11 109.8(4) . . ? C19 N3 C22 108.7(4) . . ? C11 N3 C22 113.8(4) . . ? C28 N4 C24 116.6(4) . . ? C7 O4 C8 118.1(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 20.82 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.404 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.147 # Attachment '- palladacycle.cif' data_ef02 _database_code_depnum_ccdc_archive 'CCDC 839649' #TrackingRef '- palladacycle.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H25 N3 O3.35 Pd' _chemical_formula_weight 539.88 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.6627(4) _cell_length_b 13.0584(5) _cell_length_c 17.7049(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2465.19(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9531 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 36.44 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1099.2 _exptl_absorpt_coefficient_mu 0.786 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8587 _exptl_absorpt_correction_T_max 0.8587 _exptl_absorpt_process_details 'SADABS, Sheldrick, 1997' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 86426 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 36.54 _reflns_number_total 12049 _reflns_number_gt 11383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Two disordered oxygen atoms were identified and refined using independent free variables that terminated at 0.18831 and 0.16409. Due to the low partial occupancy, these atoms were refined isotropically and hydrogen atoms were not calculated. Likewise, the unit cell contains a fractional number of atoms. ; _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^)+(0.0224P)^2^+0.3587P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.005(11) _refine_ls_number_reflns 12049 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.0504 _refine_ls_wR_factor_gt 0.0490 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.880938(7) 0.769673(7) 0.865518(4) 0.01292(2) Uani 1 1 d . . . N2 N 1.01928(9) 0.87759(8) 0.88275(5) 0.01358(17) Uani 1 1 d . . . C19 C 0.87681(12) 0.96491(9) 0.79328(6) 0.01609(18) Uani 1 1 d . . . N1 N 0.96962(9) 0.67146(8) 0.94593(6) 0.01565(18) Uani 1 1 d . . . C7 C 1.05023(11) 0.89747(10) 0.96546(6) 0.0144(2) Uani 1 1 d . . . C6 C 0.98332(12) 0.82585(9) 1.02139(6) 0.0156(2) Uani 1 1 d . . . H6A H 1.0070 0.8453 1.0723 0.019 Uiso 1 1 calc R . . H6B H 0.8935 0.8359 1.0166 0.019 Uiso 1 1 calc R . . N3 N 0.95282(10) 1.04272(8) 0.91478(6) 0.01690(18) Uani 1 1 d . . . C8 C 1.19424(12) 0.89299(11) 0.97181(7) 0.0190(2) Uani 1 1 d . . . H8A H 1.2255 0.9492 1.0023 0.023 Uiso 1 1 calc R . . H8B H 1.2209 0.8289 0.9943 0.023 Uiso 1 1 calc R . . C12 C 1.00214(12) 1.00547(10) 0.97971(7) 0.0167(2) Uani 1 1 d . . . C11 C 0.98236(11) 0.98009(9) 0.84830(6) 0.01509(19) Uani 1 1 d . . . H11A H 1.0547 1.0095 0.8219 0.018 Uiso 1 1 calc R . . C24 C 0.81512(11) 0.86999(10) 0.79302(7) 0.0157(2) Uani 1 1 d . . . C10 C 1.14076(11) 0.84327(10) 0.84739(6) 0.0181(2) Uani 1 1 d . . . H10A H 1.1430 0.8605 0.7941 0.022 Uiso 1 1 calc R . . H10B H 1.1519 0.7699 0.8530 0.022 Uiso 1 1 calc R . . C5 C 1.01167(11) 0.71393(9) 1.01065(6) 0.0151(2) Uani 1 1 d . . . C9 C 1.24127(12) 0.90165(12) 0.89074(7) 0.0210(2) Uani 1 1 d . . . H9A H 1.2459 0.9725 0.8746 0.025 Uiso 1 1 calc R . . H9B H 1.3230 0.8700 0.8849 0.025 Uiso 1 1 calc R . . C18 C 0.97300(13) 1.21645(9) 0.86377(8) 0.0227(2) Uani 1 1 d . . . H18A H 1.0447 1.1970 0.8376 0.027 Uiso 1 1 calc R . . C13 C 0.90968(12) 1.14646(10) 0.90871(7) 0.0191(2) Uani 1 1 d . . . C4 C 1.07518(12) 0.65693(10) 1.06467(7) 0.0191(2) Uani 1 1 d . . . H4A H 1.1043 0.6878 1.1086 0.023 Uiso 1 1 calc R . . C17 C 0.92772(16) 1.31613(11) 0.85843(9) 0.0286(3) Uani 1 1 d . . . H17A H 0.9700 1.3639 0.8290 0.034 Uiso 1 1 calc R . . C1 C 0.98949(12) 0.57108(10) 0.93410(8) 0.0206(2) Uani 1 1 d . . . H1A H 0.9614 0.5419 0.8893 0.025 Uiso 1 1 calc R . . C20 C 0.84639(14) 1.04061(11) 0.74038(7) 0.0224(2) Uani 1 1 d . . . H20A H 0.8894 1.1026 0.7402 0.027 Uiso 1 1 calc R . . C3 C 1.09472(13) 0.55313(11) 1.05216(9) 0.0258(3) Uani 1 1 d . . . H3A H 1.1371 0.5135 1.0876 0.031 Uiso 1 1 calc R . . C22 C 0.68944(13) 0.92922(12) 0.68747(8) 0.0252(3) Uani 1 1 d . . . H22A H 0.6264 0.9172 0.6522 0.030 Uiso 1 1 calc R . . C21 C 0.75160(14) 1.02269(12) 0.68807(8) 0.0260(3) Uani 1 1 d . . . H21A H 0.7298 1.0733 0.6535 0.031 Uiso 1 1 calc R . . C23 C 0.72109(12) 0.85361(11) 0.73936(7) 0.0214(2) Uani 1 1 d . . . H23A H 0.6791 0.7912 0.7384 0.026 Uiso 1 1 calc R . . C14 C 0.80444(15) 1.17527(12) 0.94919(11) 0.0319(3) Uani 1 1 d . . . H14A H 0.7645 1.1286 0.9807 0.038 Uiso 1 1 calc R . . C2 C 1.05020(14) 0.50952(11) 0.98613(9) 0.0266(3) Uani 1 1 d . . . H2A H 1.0609 0.4400 0.9769 0.032 Uiso 1 1 calc R . . C15 C 0.75881(16) 1.27476(14) 0.94231(12) 0.0405(4) Uani 1 1 d . . . H15A H 0.6870 1.2943 0.9684 0.049 Uiso 1 1 calc R . . C16 C 0.82016(17) 1.34455(12) 0.89671(11) 0.0348(4) Uani 1 1 d . . . H16A H 0.7890 1.4107 0.8918 0.042 Uiso 1 1 calc R . . O1 O 1.00702(11) 1.04875(8) 1.04052(5) 0.02400(19) Uani 1 1 d . . . O2 O 0.73246(8) 0.67322(7) 0.84915(5) 0.01724(16) Uani 1 1 d . . . C25 C 0.74221(12) 0.60050(10) 0.80050(7) 0.0187(2) Uani 1 1 d . . . O3 O 0.83966(10) 0.57726(10) 0.76745(7) 0.0333(3) Uani 1 1 d . . . C26 C 0.62187(16) 0.54201(12) 0.78641(8) 0.0287(3) Uani 1 1 d . . . H26A H 0.6367 0.4893 0.7497 0.043 Uiso 1 1 calc R . . H26B H 0.5589 0.5881 0.7679 0.043 Uiso 1 1 calc R . . H26C H 0.5937 0.5115 0.8328 0.043 Uiso 1 1 calc R . . O101 O 0.5211(5) 0.6845(5) 0.6183(3) 0.0286(17) Uiso 0.188(4) 1 d P . . O102 O 0.4106(5) 0.7501(4) 0.7609(3) 0.0176(15) Uiso 0.164(4) 1 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 0.01254(3) 0.01388(3) 0.01235(3) -0.00089(3) -0.00085(3) 0.00043(3) N2 0.0136(4) 0.0152(4) 0.0120(4) -0.0001(3) 0.0003(3) 0.0001(3) C19 0.0161(4) 0.0187(5) 0.0134(4) 0.0010(4) 0.0008(4) 0.0027(4) N1 0.0147(4) 0.0151(4) 0.0171(4) -0.0001(3) -0.0010(3) -0.0005(3) C7 0.0163(5) 0.0157(5) 0.0113(4) -0.0005(4) -0.0002(4) -0.0018(4) C6 0.0173(5) 0.0162(5) 0.0132(4) 0.0004(4) 0.0008(4) -0.0019(4) N3 0.0221(5) 0.0136(4) 0.0150(4) 0.0003(3) 0.0009(4) 0.0003(4) C8 0.0162(5) 0.0239(6) 0.0169(5) 0.0018(5) -0.0023(4) -0.0041(4) C12 0.0194(5) 0.0156(5) 0.0150(5) 0.0001(4) 0.0018(4) -0.0025(4) C11 0.0163(5) 0.0158(5) 0.0132(4) 0.0011(4) 0.0008(3) 0.0000(4) C24 0.0146(5) 0.0184(5) 0.0141(5) -0.0006(4) -0.0005(4) 0.0024(4) C10 0.0149(5) 0.0239(6) 0.0155(4) -0.0008(4) 0.0019(4) 0.0023(4) C5 0.0145(4) 0.0162(5) 0.0148(4) 0.0007(4) -0.0004(4) -0.0019(4) C9 0.0142(5) 0.0297(7) 0.0190(5) 0.0046(5) 0.0006(4) -0.0026(4) C18 0.0321(6) 0.0175(5) 0.0186(5) 0.0008(5) 0.0012(5) -0.0016(4) C13 0.0217(5) 0.0143(5) 0.0213(5) -0.0009(4) -0.0006(4) -0.0004(4) C4 0.0180(5) 0.0194(5) 0.0198(5) 0.0017(4) -0.0047(4) -0.0020(4) C17 0.0485(8) 0.0154(5) 0.0218(6) 0.0013(5) -0.0058(6) -0.0024(5) C1 0.0210(6) 0.0168(5) 0.0241(6) -0.0032(4) -0.0049(5) 0.0020(4) C20 0.0269(6) 0.0215(6) 0.0189(5) 0.0038(5) -0.0034(5) 0.0019(5) C3 0.0256(7) 0.0206(6) 0.0311(6) 0.0031(5) -0.0102(5) 0.0029(5) C22 0.0214(6) 0.0322(8) 0.0219(6) 0.0015(5) -0.0072(5) 0.0026(5) C21 0.0281(7) 0.0279(7) 0.0220(6) 0.0069(5) -0.0066(5) 0.0032(5) C23 0.0186(5) 0.0246(6) 0.0208(6) 0.0016(5) -0.0045(4) 0.0002(5) C14 0.0261(7) 0.0190(6) 0.0507(9) -0.0021(6) 0.0119(6) -0.0012(5) C2 0.0289(7) 0.0167(6) 0.0341(7) -0.0024(5) -0.0109(6) 0.0047(5) C15 0.0312(7) 0.0238(7) 0.0665(12) -0.0078(8) 0.0101(8) 0.0057(7) C16 0.0414(9) 0.0162(6) 0.0467(9) -0.0024(6) -0.0092(7) 0.0051(6) O1 0.0366(5) 0.0195(4) 0.0159(4) -0.0037(3) 0.0009(4) -0.0007(4) O2 0.0161(4) 0.0184(4) 0.0172(4) -0.0040(3) 0.0011(3) -0.0013(3) C25 0.0193(5) 0.0193(5) 0.0174(5) -0.0026(4) 0.0015(4) -0.0017(4) O3 0.0240(5) 0.0414(7) 0.0346(6) -0.0198(5) 0.0091(4) -0.0031(5) C26 0.0280(6) 0.0316(7) 0.0264(6) -0.0095(5) 0.0037(6) -0.0117(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 C24 1.9637(12) . ? Pd1 O2 2.0437(9) . ? Pd1 N2 2.0627(10) . ? Pd1 N1 2.1368(10) . ? N2 C10 1.5069(15) . ? N2 C11 1.5227(16) . ? N2 C7 1.5234(15) . ? C19 C20 1.3999(17) . ? C19 C24 1.4032(18) . ? C19 C11 1.5016(17) . ? N1 C1 1.3443(17) . ? N1 C5 1.3495(15) . ? C7 C12 1.5216(18) . ? C7 C6 1.5376(17) . ? C7 C8 1.5407(16) . ? C6 C5 1.5045(16) . ? N3 C12 1.3545(16) . ? N3 C13 1.4346(16) . ? N3 C11 1.4674(15) . ? C8 C9 1.5247(18) . ? C12 O1 1.2172(15) . ? C24 C23 1.3977(17) . ? C10 C9 1.5229(18) . ? C5 C4 1.3883(17) . ? C18 C13 1.3872(18) . ? C18 C17 1.3915(19) . ? C13 C14 1.384(2) . ? C4 C3 1.389(2) . ? C17 C16 1.383(2) . ? C1 C2 1.3834(19) . ? C20 C21 1.391(2) . ? C3 C2 1.384(2) . ? C22 C21 1.389(2) . ? C22 C23 1.390(2) . ? C14 C15 1.393(2) . ? C15 C16 1.382(3) . ? O2 C25 1.2862(15) . ? C25 O3 1.2307(16) . ? C25 C26 1.514(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 C24 Pd1 O2 92.38(4) . . ? C24 Pd1 N2 84.06(5) . . ? O2 Pd1 N2 174.85(4) . . ? C24 Pd1 N1 173.75(5) . . ? O2 Pd1 N1 93.87(4) . . ? N2 Pd1 N1 89.71(4) . . ? C10 N2 C11 108.49(9) . . ? C10 N2 C7 105.30(9) . . ? C11 N2 C7 106.93(9) . . ? C10 N2 Pd1 110.49(7) . . ? C11 N2 Pd1 110.88(7) . . ? C7 N2 Pd1 114.43(7) . . ? C20 C19 C24 120.86(12) . . ? C20 C19 C11 120.96(11) . . ? C24 C19 C11 118.04(10) . . ? C1 N1 C5 118.73(11) . . ? C1 N1 Pd1 123.44(9) . . ? C5 N1 Pd1 117.78(8) . . ? C12 C7 N2 104.14(10) . . ? C12 C7 C6 107.50(10) . . ? N2 C7 C6 114.51(10) . . ? C12 C7 C8 111.04(11) . . ? N2 C7 C8 106.24(10) . . ? C6 C7 C8 113.10(11) . . ? C5 C6 C7 114.60(10) . . ? C12 N3 C13 121.81(11) . . ? C12 N3 C11 113.41(10) . . ? C13 N3 C11 122.34(10) . . ? C9 C8 C7 104.85(10) . . ? O1 C12 N3 126.92(12) . . ? O1 C12 C7 124.23(11) . . ? N3 C12 C7 108.85(10) . . ? N3 C11 C19 115.66(10) . . ? N3 C11 N2 102.95(8) . . ? C19 C11 N2 109.73(9) . . ? C23 C24 C19 118.27(11) . . ? C23 C24 Pd1 126.77(10) . . ? C19 C24 Pd1 114.81(8) . . ? N2 C10 C9 104.28(9) . . ? N1 C5 C4 121.78(11) . . ? N1 C5 C6 116.08(10) . . ? C4 C5 C6 122.12(11) . . ? C10 C9 C8 101.88(10) . . ? C13 C18 C17 119.10(13) . . ? C14 C13 C18 120.84(13) . . ? C14 C13 N3 118.56(12) . . ? C18 C13 N3 120.60(11) . . ? C5 C4 C3 119.11(12) . . ? C16 C17 C18 120.37(15) . . ? N1 C1 C2 122.45(12) . . ? C21 C20 C19 119.68(13) . . ? C2 C3 C4 118.99(13) . . ? C21 C22 C23 120.20(13) . . ? C22 C21 C20 119.99(13) . . ? C22 C23 C24 120.98(13) . . ? C13 C14 C15 119.46(15) . . ? C1 C2 C3 118.93(13) . . ? C16 C15 C14 120.05(15) . . ? C15 C16 C17 120.12(15) . . ? C25 O2 Pd1 119.17(8) . . ? O3 C25 O2 124.67(12) . . ? O3 C25 C26 120.85(12) . . ? O2 C25 C26 114.48(11) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 36.54 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.673 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.063