# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prasenjit Ghosh' _publ_contact_author_email PGHOSH@CHEM.IITB.AC.IN _publ_section_title ; Palladium Complexes of Abnormal N-heterocyclic Carbenes as Precatalysts for the Much Preferred Cu-free and Amine-free Sonogashira Coupling in Air in a Mixed-aqueous Medium ; loop_ _publ_author_name 'Prasenjit Ghosh' 'Alex John' 'Mobin M. Shaikh' #===END data_pg207 _database_code_depnum_ccdc_archive 'CCDC 687466' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 I2 N3 Pd' _chemical_formula_weight 661.58 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' I I -0.4742 1.8119 '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 21/n' 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 10.1323(2) _cell_length_b 14.5426(3) _cell_length_c 14.3889(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.569(2) _cell_angle_gamma 90.00 _cell_volume 2118.07(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10115 _cell_measurement_theta_min 3.1308 _cell_measurement_theta_max 32.4554 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.075 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 3.800 _exptl_absorpt_correction_T_min 0.3416 _exptl_absorpt_correction_T_max 0.4159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11082 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3718 _reflns_number_gt 3275 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0204P)^2^+1.3146P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3718 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0175 _refine_ls_wR_factor_ref 0.0402 _refine_ls_wR_factor_gt 0.0392 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.520049(19) 0.186470(14) 0.487120(13) 0.01969(6) Uani 1 1 d . . . I1 I 0.639062(18) 0.108296(13) 0.630956(12) 0.02965(6) Uani 1 1 d . . . I2 I 0.412906(17) 0.259266(14) 0.337036(12) 0.02903(6) Uani 1 1 d . . . N1 N 0.7437(2) 0.13863(15) 0.36990(14) 0.0210(5) Uani 1 1 d . . . N2 N 0.8967(2) 0.24278(15) 0.39151(15) 0.0236(5) Uani 1 1 d . . . N3 N 0.3334(2) 0.17222(16) 0.54324(15) 0.0245(5) Uani 1 1 d . . . C1 C 0.6935(2) 0.20143(19) 0.43262(17) 0.0214(6) Uani 1 1 d . . . C2 C 0.7895(2) 0.26622(19) 0.44527(18) 0.0218(6) Uani 1 1 d . . . C3 C 1.0139(3) 0.3008(2) 0.3813(2) 0.0330(7) Uani 1 1 d . . . H3A H 1.0908 0.2715 0.4126 0.050 Uiso 1 1 calc R . . H3B H 0.9991 0.3611 0.4093 0.050 Uiso 1 1 calc R . . H3C H 1.0300 0.3085 0.3151 0.050 Uiso 1 1 calc R . . C4 C 0.8683(2) 0.16371(19) 0.34532(17) 0.0213(6) Uani 1 1 d . . . C5 C 1.0781(3) 0.1304(2) 0.2574(2) 0.0404(8) Uani 1 1 d . . . H5A H 1.1122 0.0797 0.2205 0.061 Uiso 1 1 calc R . . H5B H 1.1342 0.1384 0.3141 0.061 Uiso 1 1 calc R . . H5C H 1.0784 0.1872 0.2207 0.061 Uiso 1 1 calc R . . C6 C 0.9392(3) 0.1089(2) 0.28314(19) 0.0267(6) Uani 1 1 d . . . C7 C 0.8740(3) 0.0338(2) 0.24759(19) 0.0335(7) Uani 1 1 d . . . H7 H 0.9176 -0.0047 0.2053 0.040 Uiso 1 1 calc R . . C8 C 0.7443(3) 0.0108(2) 0.2710(2) 0.0323(7) Uani 1 1 d . . . H8 H 0.7016 -0.0411 0.2431 0.039 Uiso 1 1 calc R . . C9 C 0.6809(3) 0.06195(19) 0.33266(19) 0.0259(6) Uani 1 1 d . . . H9 H 0.5947 0.0457 0.3502 0.031 Uiso 1 1 calc R . . C10 C 0.7875(3) 0.35095(19) 0.50087(18) 0.0234(6) Uani 1 1 d . . . C11 C 0.8789(3) 0.3682(2) 0.5734(2) 0.0410(8) Uani 1 1 d . . . H11 H 0.9466 0.3245 0.5877 0.049 Uiso 1 1 calc R . . C12 C 0.8730(3) 0.4480(2) 0.6253(2) 0.0420(8) Uani 1 1 d . . . H12 H 0.9356 0.4580 0.6754 0.050 Uiso 1 1 calc R . . C13 C 0.7779(3) 0.5129(2) 0.6052(2) 0.0312(7) Uani 1 1 d . . . H13 H 0.7756 0.5684 0.6400 0.037 Uiso 1 1 calc R . . C14 C 0.6854(3) 0.4967(2) 0.5337(2) 0.0378(7) Uani 1 1 d . . . H14 H 0.6186 0.5410 0.5195 0.045 Uiso 1 1 calc R . . C15 C 0.6893(3) 0.4156(2) 0.4824(2) 0.0340(7) Uani 1 1 d . . . H15 H 0.6241 0.4045 0.4342 0.041 Uiso 1 1 calc R . . C16 C 0.2962(3) 0.2233(2) 0.6149(2) 0.0342(7) Uani 1 1 d . . . H16 H 0.3585 0.2647 0.6430 0.041 Uiso 1 1 calc R . . C17 C 0.1724(3) 0.2187(2) 0.6495(2) 0.0387(8) Uani 1 1 d . . . H17 H 0.1505 0.2559 0.7009 0.046 Uiso 1 1 calc R . . C18 C 0.0806(3) 0.1599(2) 0.6093(2) 0.0383(8) Uani 1 1 d . . . H18 H -0.0057 0.1553 0.6322 0.046 Uiso 1 1 calc R . . C19 C 0.1175(3) 0.1075(2) 0.5342(2) 0.0371(7) Uani 1 1 d . . . H19 H 0.0559 0.0670 0.5039 0.045 Uiso 1 1 calc R . . C20 C 0.2438(3) 0.1145(2) 0.5042(2) 0.0300(7) Uani 1 1 d . . . H20 H 0.2687 0.0772 0.4537 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.01507(10) 0.02450(12) 0.01968(11) -0.00259(8) 0.00290(7) -0.00076(8) I1 0.03018(11) 0.03531(12) 0.02338(10) 0.00121(8) 0.00034(7) 0.00314(8) I2 0.02022(10) 0.04101(12) 0.02594(10) 0.00414(8) 0.00208(7) 0.00244(8) N1 0.0191(12) 0.0232(12) 0.0205(11) -0.0002(9) -0.0005(9) 0.0011(9) N2 0.0170(12) 0.0276(13) 0.0263(12) -0.0006(10) 0.0017(9) -0.0019(10) N3 0.0205(12) 0.0289(13) 0.0242(12) -0.0033(10) 0.0025(9) -0.0020(10) C1 0.0176(13) 0.0257(15) 0.0209(13) -0.0009(11) 0.0012(10) 0.0034(11) C2 0.0161(13) 0.0272(15) 0.0221(14) 0.0010(11) 0.0014(10) 0.0019(11) C3 0.0223(15) 0.0365(18) 0.0408(18) 0.0004(14) 0.0080(12) -0.0072(13) C4 0.0142(13) 0.0272(15) 0.0226(14) 0.0041(11) 0.0010(10) 0.0005(11) C5 0.0280(17) 0.053(2) 0.0415(19) -0.0073(16) 0.0134(13) 0.0033(15) C6 0.0226(15) 0.0337(17) 0.0240(14) 0.0002(12) 0.0044(11) 0.0059(12) C7 0.0357(18) 0.0387(18) 0.0267(16) -0.0072(13) 0.0075(12) 0.0108(14) C8 0.0358(17) 0.0288(16) 0.0320(16) -0.0089(13) -0.0002(12) -0.0014(14) C9 0.0223(15) 0.0270(16) 0.0282(15) 0.0000(12) -0.0003(11) -0.0022(12) C10 0.0194(14) 0.0241(15) 0.0268(15) 0.0002(11) 0.0028(11) -0.0018(11) C11 0.0376(19) 0.0324(18) 0.051(2) -0.0075(15) -0.0176(15) 0.0096(14) C12 0.0399(19) 0.041(2) 0.0433(19) -0.0109(15) -0.0160(14) -0.0009(15) C13 0.0307(16) 0.0262(16) 0.0373(17) -0.0077(13) 0.0073(12) -0.0072(13) C14 0.0347(18) 0.0322(18) 0.0460(19) -0.0034(15) -0.0049(14) 0.0085(14) C15 0.0334(17) 0.0348(18) 0.0333(17) -0.0025(13) -0.0070(13) 0.0030(14) C16 0.0262(16) 0.0425(19) 0.0345(17) -0.0121(14) 0.0066(12) -0.0018(14) C17 0.0282(17) 0.052(2) 0.0371(18) -0.0069(15) 0.0116(13) 0.0070(15) C18 0.0248(16) 0.045(2) 0.0461(19) 0.0101(16) 0.0132(13) 0.0029(14) C19 0.0276(17) 0.0376(19) 0.0458(19) 0.0063(15) -0.0016(13) -0.0107(14) C20 0.0305(16) 0.0314(17) 0.0285(15) -0.0005(13) 0.0062(12) -0.0048(13) _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 C1 1.968(3) . ? Pd1 N3 2.100(2) . ? Pd1 I2 2.5986(3) . ? Pd1 I1 2.6089(3) . ? N1 C4 1.376(3) . ? N1 C9 1.380(3) . ? N1 C1 1.396(3) . ? N2 C4 1.353(3) . ? N2 C2 1.403(3) . ? N2 C3 1.470(3) . ? N3 C16 1.338(4) . ? N3 C20 1.341(4) . ? C1 C2 1.361(4) . ? C2 C10 1.470(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C6 1.418(4) . ? C5 C6 1.504(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.365(4) . ? C7 C8 1.411(4) . ? C7 H7 0.9500 . ? C8 C9 1.343(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C15 1.386(4) . ? C10 C11 1.387(4) . ? C11 C12 1.383(4) . ? C11 H11 0.9500 . ? C12 C13 1.370(4) . ? C12 H12 0.9500 . ? C13 C14 1.380(4) . ? C13 H13 0.9500 . ? C14 C15 1.393(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.372(4) . ? C16 H16 0.9500 . ? C17 C18 1.373(5) . ? C17 H17 0.9500 . ? C18 C19 1.388(5) . ? C18 H18 0.9500 . ? C19 C20 1.373(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? 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 C1 Pd1 N3 178.87(10) . . ? C1 Pd1 I2 88.34(7) . . ? N3 Pd1 I2 90.56(6) . . ? C1 Pd1 I1 88.57(7) . . ? N3 Pd1 I1 92.53(6) . . ? I2 Pd1 I1 176.218(10) . . ? C4 N1 C9 121.8(2) . . ? C4 N1 C1 111.0(2) . . ? C9 N1 C1 127.2(2) . . ? C4 N2 C2 108.9(2) . . ? C4 N2 C3 126.5(2) . . ? C2 N2 C3 124.4(2) . . ? C16 N3 C20 117.5(2) . . ? C16 N3 Pd1 122.04(19) . . ? C20 N3 Pd1 120.32(18) . . ? C2 C1 N1 105.1(2) . . ? C2 C1 Pd1 132.0(2) . . ? N1 C1 Pd1 122.87(19) . . ? C1 C2 N2 108.9(2) . . ? C1 C2 C10 128.7(2) . . ? N2 C2 C10 122.3(2) . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 N1 106.1(2) . . ? N2 C4 C6 133.2(2) . . ? N1 C4 C6 120.7(2) . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C4 115.8(3) . . ? C7 C6 C5 121.2(3) . . ? C4 C6 C5 123.0(3) . . ? C6 C7 C8 122.7(3) . . ? C6 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? C9 C8 C7 120.3(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 N1 118.6(3) . . ? C8 C9 H9 120.7 . . ? N1 C9 H9 120.7 . . ? C15 C10 C11 118.1(3) . . ? C15 C10 C2 119.4(2) . . ? C11 C10 C2 122.4(3) . . ? C12 C11 C10 121.0(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.1(3) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 120.3(3) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C10 C15 C14 120.6(3) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? N3 C16 C17 123.1(3) . . ? N3 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C16 C17 C18 119.4(3) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 118.0(3) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? C20 C19 C18 119.5(3) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? N3 C20 C19 122.5(3) . . ? N3 C20 H20 118.7 . . ? C19 C20 H20 118.7 . . ? 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 C1 Pd1 N3 C16 -96(5) . . . . ? I2 Pd1 N3 C16 -109.8(2) . . . . ? I1 Pd1 N3 C16 72.4(2) . . . . ? C1 Pd1 N3 C20 80(5) . . . . ? I2 Pd1 N3 C20 66.2(2) . . . . ? I1 Pd1 N3 C20 -111.6(2) . . . . ? C4 N1 C1 C2 0.6(3) . . . . ? C9 N1 C1 C2 -177.6(2) . . . . ? C4 N1 C1 Pd1 -177.83(17) . . . . ? C9 N1 C1 Pd1 4.0(4) . . . . ? N3 Pd1 C1 C2 86(5) . . . . ? I2 Pd1 C1 C2 99.1(3) . . . . ? I1 Pd1 C1 C2 -83.0(3) . . . . ? N3 Pd1 C1 N1 -96(5) . . . . ? I2 Pd1 C1 N1 -82.9(2) . . . . ? I1 Pd1 C1 N1 95.0(2) . . . . ? N1 C1 C2 N2 -0.4(3) . . . . ? Pd1 C1 C2 N2 177.89(19) . . . . ? N1 C1 C2 C10 176.8(3) . . . . ? Pd1 C1 C2 C10 -4.9(4) . . . . ? C4 N2 C2 C1 0.0(3) . . . . ? C3 N2 C2 C1 174.5(2) . . . . ? C4 N2 C2 C10 -177.4(2) . . . . ? C3 N2 C2 C10 -2.9(4) . . . . ? C2 N2 C4 N1 0.4(3) . . . . ? C3 N2 C4 N1 -174.0(2) . . . . ? C2 N2 C4 C6 -179.2(3) . . . . ? C3 N2 C4 C6 6.4(5) . . . . ? C9 N1 C4 N2 177.7(2) . . . . ? C1 N1 C4 N2 -0.6(3) . . . . ? C9 N1 C4 C6 -2.6(4) . . . . ? C1 N1 C4 C6 179.0(2) . . . . ? N2 C4 C6 C7 -177.8(3) . . . . ? N1 C4 C6 C7 2.6(4) . . . . ? N2 C4 C6 C5 2.6(5) . . . . ? N1 C4 C6 C5 -177.0(2) . . . . ? C4 C6 C7 C8 -0.4(4) . . . . ? C5 C6 C7 C8 179.2(3) . . . . ? C6 C7 C8 C9 -2.0(5) . . . . ? C7 C8 C9 N1 2.1(4) . . . . ? C4 N1 C9 C8 0.2(4) . . . . ? C1 N1 C9 C8 178.2(3) . . . . ? C1 C2 C10 C15 -57.3(4) . . . . ? N2 C2 C10 C15 119.5(3) . . . . ? C1 C2 C10 C11 121.1(3) . . . . ? N2 C2 C10 C11 -62.1(4) . . . . ? C15 C10 C11 C12 -0.6(5) . . . . ? C2 C10 C11 C12 -179.0(3) . . . . ? C10 C11 C12 C13 -1.2(5) . . . . ? C11 C12 C13 C14 1.7(5) . . . . ? C12 C13 C14 C15 -0.4(5) . . . . ? C11 C10 C15 C14 1.8(4) . . . . ? C2 C10 C15 C14 -179.7(3) . . . . ? C13 C14 C15 C10 -1.3(5) . . . . ? C20 N3 C16 C17 0.3(5) . . . . ? Pd1 N3 C16 C17 176.4(2) . . . . ? N3 C16 C17 C18 -0.6(5) . . . . ? C16 C17 C18 C19 -0.3(5) . . . . ? C17 C18 C19 C20 1.3(5) . . . . ? C16 N3 C20 C19 0.8(4) . . . . ? Pd1 N3 C20 C19 -175.4(2) . . . . ? C18 C19 C20 N3 -1.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.484 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.071 # Attachment 'AJ_Combined.cif' data_pg209 _database_code_depnum_ccdc_archive 'CCDC 688351' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H34 I4 N6 Pd2' _chemical_formula_weight 1295.11 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' I I -0.4742 1.8119 '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 n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 9.5091(13) _cell_length_b 14.4540(18) _cell_length_c 14.6883(14) _cell_angle_alpha 90.000 _cell_angle_beta 93.267(10) _cell_angle_gamma 90.000 _cell_volume 2015.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4935 _cell_measurement_theta_min 2.9604 _cell_measurement_theta_max 32.5835 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 3.991 _exptl_absorpt_correction_T_min 0.4879 _exptl_absorpt_correction_T_max 0.5859 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12598 _diffrn_reflns_av_R_equivalents 0.0921 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6084 _reflns_number_gt 5197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0887P)^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 riding _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 0.52(4) _refine_ls_number_reflns 6084 _refine_ls_number_parameters 453 _refine_ls_number_restraints 50 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1387 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.044 _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 0.40262(11) 0.90804(7) 0.15029(8) 0.0254(2) Uani 1 1 d . . . Pd2 Pd 0.40087(10) 1.54913(8) 0.10188(7) 0.0265(3) Uani 1 1 d . . . I1 I 0.26440(9) 0.84838(7) 0.00349(6) 0.0346(3) Uani 1 1 d . . . I2 I 0.52483(9) 0.95270(7) 0.30667(7) 0.0361(3) Uani 1 1 d . . . I3 I 0.29538(10) 1.48945(7) -0.05414(7) 0.0344(3) Uani 1 1 d . . . I4 I 0.51962(10) 1.63101(7) 0.24436(7) 0.0361(3) Uani 1 1 d . . . N1 N 0.0167(14) 0.9870(8) 0.2490(10) 0.034(3) Uani 1 1 d . . . N2 N 0.1536(14) 0.8661(9) 0.2614(9) 0.032(3) Uani 1 1 d . . . N3 N 0.5979(14) 0.9041(8) 0.0858(8) 0.031(3) Uani 1 1 d . . . N4 N 0.7916(13) 1.4655(9) 0.0102(10) 0.036(3) Uani 1 1 d . . . N5 N 0.6511(13) 1.5830(8) -0.0048(8) 0.027(3) Uani 1 1 d . . . N6 N 0.1952(13) 1.5616(8) 0.1498(8) 0.030(3) Uani 1 1 d . . . C1 C 0.2209(19) 0.9278(11) 0.2069(11) 0.039(4) Uani 1 1 d . . . C2 C 0.1405(17) 1.0034(10) 0.1997(11) 0.034(4) Uani 1 1 d . . . C3 C 0.0268(16) 0.9027(10) 0.2865(10) 0.029(3) Uani 1 1 d . . . C4 C -0.063(2) 0.8506(12) 0.3395(12) 0.044(4) Uani 1 1 d . . . H4 H -0.1498 0.8745 0.3575 0.053 Uiso 1 1 calc R . . C5 C -0.0182(15) 0.7652(11) 0.3634(11) 0.033(4) Uani 1 1 d . . . H5 H -0.0777 0.7275 0.3976 0.040 Uiso 1 1 calc R . . C6 C 0.1114(17) 0.7297(11) 0.3402(11) 0.036(4) Uani 1 1 d . . . H6 H 0.1411 0.6707 0.3623 0.043 Uiso 1 1 calc R . . C7 C 0.1941(15) 0.7778(11) 0.2872(10) 0.032(3) Uani 1 1 d . . . H7 H 0.2790 0.7519 0.2675 0.038 Uiso 1 1 calc R . . C8 C -0.0992(17) 1.0509(12) 0.2634(12) 0.042(4) Uani 1 1 d . . . H8A H -0.1871 1.0251 0.2361 0.063 Uiso 1 1 calc R . . H8B H -0.0800 1.1105 0.2349 0.063 Uiso 1 1 calc R . . H8C H -0.1081 1.0598 0.3290 0.063 Uiso 1 1 calc R . . C9 C 0.1561(15) 1.0902(10) 0.1495(12) 0.037(3) Uani 1 1 d DU . . C10 C 0.2652(17) 1.1472(11) 0.1727(14) 0.058(5) Uani 1 1 d DU . . H10 H 0.3297 1.1321 0.2223 0.070 Uiso 1 1 calc R . . C11 C 0.2820(18) 1.2282(13) 0.1233(15) 0.072(6) Uani 1 1 d DU . . H11 H 0.3577 1.2687 0.1404 0.086 Uiso 1 1 calc R . . C12 C 0.1926(19) 1.2509(12) 0.0512(13) 0.060(5) Uani 1 1 d DU . . H12 H 0.2052 1.3063 0.0180 0.072 Uiso 1 1 calc R . . C13 C 0.085(3) 1.1925(11) 0.0281(13) 0.066(5) Uani 1 1 d DU . . H13 H 0.0214 1.2066 -0.0220 0.079 Uiso 1 1 calc R . . C14 C 0.069(2) 1.1137(11) 0.0768(13) 0.057(5) Uani 1 1 d DU . . H14 H -0.0059 1.0732 0.0591 0.069 Uiso 1 1 calc R . . C15 C 0.6110(16) 0.9557(11) 0.0120(12) 0.038(4) Uani 1 1 d . . . H15 H 0.5304 0.9879 -0.0127 0.046 Uiso 1 1 calc R . . C16 C 0.7307(16) 0.9646(12) -0.0288(11) 0.038(4) Uani 1 1 d . . . H16 H 0.7361 1.0045 -0.0799 0.046 Uiso 1 1 calc R . . C17 C 0.8497(18) 0.9146(11) 0.0040(11) 0.035(4) Uani 1 1 d . . . H17 H 0.9361 0.9173 -0.0255 0.042 Uiso 1 1 calc R . . C18 C 0.8352(15) 0.8612(10) 0.0813(9) 0.028(3) Uani 1 1 d . . . H18 H 0.9140 0.8280 0.1071 0.033 Uiso 1 1 calc R . . C19 C 0.7120(17) 0.8558(10) 0.1197(10) 0.031(3) Uani 1 1 d . . . H19 H 0.7036 0.8176 0.1717 0.038 Uiso 1 1 calc R . . C20 C 0.5857(17) 1.5239(9) 0.0558(10) 0.030(3) Uani 1 1 d . . . C21 C 0.6750(15) 1.4515(10) 0.0672(10) 0.026(3) Uani 1 1 d . . . C22 C 0.7752(15) 1.5451(10) -0.0295(10) 0.029(3) Uani 1 1 d . . . C23 C 0.8587(16) 1.5928(11) -0.0910(11) 0.031(3) Uani 1 1 d . . . H23 H 0.9444 1.5680 -0.1107 0.037 Uiso 1 1 calc R . . C24 C 0.8087(17) 1.6759(11) -0.1199(13) 0.038(4) Uani 1 1 d . . . H24 H 0.8651 1.7114 -0.1581 0.046 Uiso 1 1 calc R . . C25 C 0.6839(19) 1.7119(12) -0.0980(12) 0.044(4) Uani 1 1 d . . . H25 H 0.6528 1.7690 -0.1241 0.053 Uiso 1 1 calc R . . C26 C 0.6016(15) 1.6666(10) -0.0382(12) 0.032(4) Uani 1 1 d . . . H26 H 0.5149 1.6917 -0.0207 0.039 Uiso 1 1 calc R . . C27 C 0.9178(17) 1.4070(13) 0.0085(13) 0.043(4) Uani 1 1 d . . . H27A H 0.9248 1.3681 0.0632 0.064 Uiso 1 1 calc R . . H27B H 1.0016 1.4463 0.0071 0.064 Uiso 1 1 calc R . . H27C H 0.9112 1.3677 -0.0459 0.064 Uiso 1 1 calc R . . C28 C 0.6650(15) 1.3697(9) 0.1247(11) 0.031(3) Uani 1 1 d . . . C29 C 0.6719(19) 1.2817(12) 0.0861(11) 0.041(4) Uani 1 1 d . . . H29 H 0.6849 1.2750 0.0228 0.050 Uiso 1 1 calc R . . C30 C 0.660(2) 1.2032(13) 0.1415(14) 0.061(6) Uani 1 1 d . . . H30 H 0.6598 1.1429 0.1159 0.074 Uiso 1 1 calc R . . C31 C 0.6468(18) 1.2158(12) 0.2373(13) 0.045(4) Uani 1 1 d . . . H31 H 0.6369 1.1635 0.2755 0.054 Uiso 1 1 calc R . . C32 C 0.6488(18) 1.2999(11) 0.2728(12) 0.040(4) Uani 1 1 d . . . H32 H 0.6451 1.3071 0.3369 0.049 Uiso 1 1 calc R . . C33 C 0.6561(15) 1.3780(10) 0.2176(12) 0.035(4) Uani 1 1 d . . . H33 H 0.6550 1.4378 0.2445 0.042 Uiso 1 1 calc R . . C34 C 0.1033(17) 1.6207(11) 0.1174(10) 0.033(4) Uani 1 1 d . . . H34 H 0.1313 1.6646 0.0738 0.040 Uiso 1 1 calc R . . C35 C -0.0338(15) 1.6227(10) 0.1437(11) 0.030(3) Uani 1 1 d . . . H35 H -0.0994 1.6669 0.1191 0.036 Uiso 1 1 calc R . . C36 C -0.0733(16) 1.5563(13) 0.2088(12) 0.040(4) Uani 1 1 d . . . H36 H -0.1668 1.5540 0.2282 0.048 Uiso 1 1 calc R . . C37 C 0.0233(18) 1.4983(12) 0.2414(13) 0.044(4) Uani 1 1 d . . . H37 H -0.0007 1.4536 0.2853 0.053 Uiso 1 1 calc R . . C38 C 0.1580(18) 1.5010(12) 0.2131(11) 0.039(4) Uani 1 1 d . . . H38 H 0.2263 1.4592 0.2388 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.0229(6) 0.0275(5) 0.0265(6) -0.0013(4) 0.0067(4) 0.0004(4) Pd2 0.0220(6) 0.0336(6) 0.0245(6) 0.0007(4) 0.0067(4) 0.0030(4) I1 0.0302(5) 0.0458(6) 0.0281(6) -0.0020(4) 0.0041(4) -0.0042(4) I2 0.0291(5) 0.0492(6) 0.0305(6) -0.0087(4) 0.0058(4) -0.0001(4) I3 0.0287(5) 0.0451(6) 0.0300(5) -0.0039(4) 0.0076(4) -0.0056(4) I4 0.0303(6) 0.0465(6) 0.0318(6) -0.0072(4) 0.0032(4) 0.0094(4) N1 0.039(8) 0.025(6) 0.038(8) -0.006(6) 0.010(6) -0.001(6) N2 0.030(7) 0.031(7) 0.035(8) -0.010(5) -0.003(6) 0.002(5) N3 0.049(8) 0.029(7) 0.015(6) 0.003(5) 0.013(6) 0.002(6) N4 0.031(8) 0.034(8) 0.043(9) 0.002(6) -0.003(6) 0.003(5) N5 0.027(7) 0.028(7) 0.026(7) -0.006(5) 0.003(5) 0.000(5) N6 0.029(7) 0.032(7) 0.028(7) 0.007(5) 0.001(5) 0.012(5) C1 0.058(11) 0.026(8) 0.032(9) -0.007(6) -0.004(8) 0.003(7) C2 0.044(10) 0.033(9) 0.028(9) -0.008(6) 0.024(7) -0.004(7) C3 0.030(9) 0.038(9) 0.021(8) -0.005(6) 0.012(6) 0.002(6) C4 0.052(11) 0.045(11) 0.038(10) -0.007(8) 0.026(8) 0.000(8) C5 0.017(8) 0.049(10) 0.036(9) 0.004(7) 0.015(6) -0.002(6) C6 0.039(10) 0.036(9) 0.033(9) 0.007(7) 0.017(7) -0.003(7) C7 0.018(8) 0.047(9) 0.032(9) -0.003(7) 0.006(6) 0.007(6) C8 0.034(9) 0.045(10) 0.048(11) -0.016(8) 0.005(8) 0.020(7) C9 0.032(8) 0.019(7) 0.061(10) -0.009(7) 0.019(7) 0.010(5) C10 0.037(9) 0.047(10) 0.092(14) 0.025(9) 0.009(9) -0.008(7) C11 0.033(10) 0.041(10) 0.142(17) 0.031(10) 0.023(9) 0.000(8) C12 0.060(11) 0.025(8) 0.099(14) 0.018(8) 0.044(8) 0.017(6) C13 0.113(15) 0.020(8) 0.064(12) -0.003(7) -0.010(11) 0.012(8) C14 0.082(13) 0.028(8) 0.060(12) 0.004(7) -0.012(9) -0.008(8) C15 0.019(8) 0.043(10) 0.053(11) 0.007(8) 0.008(7) -0.005(6) C16 0.031(9) 0.053(10) 0.033(9) 0.009(7) 0.008(7) -0.006(7) C17 0.039(10) 0.039(9) 0.028(9) -0.002(7) 0.012(7) -0.006(7) C18 0.025(8) 0.043(9) 0.015(7) 0.000(6) 0.004(6) 0.014(6) C19 0.036(9) 0.034(8) 0.025(8) -0.003(6) 0.003(7) 0.000(6) C20 0.043(9) 0.015(7) 0.033(9) 0.000(6) 0.007(7) -0.008(6) C21 0.016(7) 0.037(9) 0.028(8) -0.005(6) 0.014(6) -0.002(6) C22 0.024(8) 0.034(9) 0.029(9) -0.005(6) 0.013(6) 0.001(6) C23 0.024(8) 0.035(9) 0.036(9) -0.008(7) 0.009(6) -0.001(6) C24 0.026(9) 0.038(9) 0.054(11) -0.012(7) 0.022(7) -0.015(7) C25 0.040(10) 0.042(10) 0.049(11) -0.001(8) 0.002(8) 0.006(8) C26 0.016(8) 0.031(8) 0.051(11) -0.001(7) 0.006(7) -0.005(6) C27 0.025(9) 0.058(12) 0.047(11) -0.005(8) 0.015(7) 0.017(7) C28 0.022(8) 0.020(7) 0.050(10) 0.003(6) 0.001(7) 0.005(6) C29 0.053(11) 0.042(10) 0.030(9) 0.002(7) 0.010(7) 0.003(8) C30 0.081(15) 0.038(11) 0.064(14) -0.008(9) -0.007(11) 0.018(10) C31 0.040(10) 0.039(10) 0.055(11) 0.004(8) -0.007(8) 0.002(7) C32 0.044(10) 0.043(10) 0.036(9) 0.012(7) 0.014(7) 0.010(7) C33 0.024(8) 0.024(8) 0.057(11) 0.002(7) 0.010(7) 0.002(6) C34 0.041(10) 0.038(9) 0.021(8) 0.004(6) 0.003(7) -0.019(7) C35 0.016(7) 0.032(8) 0.044(10) -0.008(6) 0.012(7) 0.010(6) C36 0.015(8) 0.065(12) 0.041(10) -0.003(8) 0.007(7) 0.010(7) C37 0.036(10) 0.055(10) 0.044(11) 0.007(8) 0.021(8) -0.005(8) C38 0.039(10) 0.044(10) 0.036(10) 0.013(7) 0.012(7) -0.002(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 Pd1 C1 1.980(19) . ? Pd1 N3 2.133(13) . ? Pd1 I2 2.5959(15) . ? Pd1 I1 2.6073(14) . ? Pd2 C20 1.954(16) . ? Pd2 N6 2.123(13) . ? Pd2 I3 2.5961(14) . ? Pd2 I4 2.6051(14) . ? N1 C3 1.34(2) . ? N1 C2 1.44(2) . ? N1 C8 1.461(19) . ? N2 C3 1.385(19) . ? N2 C1 1.38(2) . ? N2 C7 1.38(2) . ? N3 C15 1.33(2) . ? N3 C19 1.36(2) . ? N4 C22 1.295(19) . ? N4 C21 1.44(2) . ? N4 C27 1.469(19) . ? N5 C22 1.369(19) . ? N5 C26 1.376(19) . ? N5 C20 1.404(19) . ? N6 C34 1.29(2) . ? N6 C38 1.34(2) . ? C1 C2 1.33(2) . ? C2 C9 1.47(2) . ? C3 C4 1.40(2) . ? C4 C5 1.34(2) . ? C4 H4 0.9500 . ? C5 C6 1.40(2) . ? C5 H5 0.9500 . ? C6 C7 1.33(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.354(18) . ? C9 C14 1.35(3) . ? C10 C11 1.39(3) . ? C10 H10 0.9500 . ? C11 C12 1.36(2) . ? C11 H11 0.9500 . ? C12 C13 1.35(3) . ? C12 H12 0.9500 . ? C13 C14 1.359(18) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.32(2) . ? C15 H15 0.9500 . ? C16 C17 1.40(2) . ? C16 H16 0.9500 . ? C17 C18 1.39(2) . ? C17 H17 0.9500 . ? C18 C19 1.33(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.35(2) . ? C21 C28 1.46(2) . ? C22 C23 1.42(2) . ? C23 C24 1.35(2) . ? C23 H23 0.9500 . ? C24 C25 1.35(2) . ? C24 H24 0.9500 . ? C25 C26 1.38(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.39(2) . ? C28 C33 1.38(2) . ? C29 C30 1.41(3) . ? C29 H29 0.9500 . ? C30 C31 1.43(3) . ? C30 H30 0.9500 . ? C31 C32 1.32(2) . ? C31 H31 0.9500 . ? C32 C33 1.39(2) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C35 1.38(2) . ? C34 H34 0.9500 . ? C35 C36 1.42(2) . ? C35 H35 0.9500 . ? C36 C37 1.31(2) . ? C36 H36 0.9500 . ? C37 C38 1.37(2) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? 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 C1 Pd1 N3 173.1(6) . . ? C1 Pd1 I2 87.1(5) . . ? N3 Pd1 I2 92.4(3) . . ? C1 Pd1 I1 89.1(5) . . ? N3 Pd1 I1 92.0(3) . . ? I2 Pd1 I1 173.30(6) . . ? C20 Pd2 N6 174.0(5) . . ? C20 Pd2 I3 86.7(4) . . ? N6 Pd2 I3 90.2(3) . . ? C20 Pd2 I4 90.3(4) . . ? N6 Pd2 I4 93.5(3) . . ? I3 Pd2 I4 171.15(6) . . ? C3 N1 C2 108.4(13) . . ? C3 N1 C8 123.5(14) . . ? C2 N1 C8 128.0(14) . . ? C3 N2 C1 110.4(13) . . ? C3 N2 C7 120.9(14) . . ? C1 N2 C7 128.7(14) . . ? C15 N3 C19 118.6(14) . . ? C15 N3 Pd1 118.2(10) . . ? C19 N3 Pd1 123.2(10) . . ? C22 N4 C21 108.1(12) . . ? C22 N4 C27 125.5(14) . . ? C21 N4 C27 125.8(14) . . ? C22 N5 C26 122.7(13) . . ? C22 N5 C20 110.1(12) . . ? C26 N5 C20 127.2(13) . . ? C34 N6 C38 119.2(14) . . ? C34 N6 Pd2 123.4(11) . . ? C38 N6 Pd2 117.3(10) . . ? C2 C1 N2 107.0(16) . . ? C2 C1 Pd1 126.5(13) . . ? N2 C1 Pd1 126.6(11) . . ? C1 C2 N1 107.9(14) . . ? C1 C2 C9 131.7(16) . . ? N1 C2 C9 120.2(13) . . ? N1 C3 N2 106.3(13) . . ? N1 C3 C4 133.2(15) . . ? N2 C3 C4 120.5(15) . . ? C5 C4 C3 116.5(16) . . ? C5 C4 H4 121.8 . . ? C3 C4 H4 121.8 . . ? C4 C5 C6 122.8(15) . . ? C4 C5 H5 118.6 . . ? C6 C5 H5 118.6 . . ? C7 C6 C5 120.6(15) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 N2 118.6(14) . . ? C6 C7 H7 120.7 . . ? N2 C7 H7 120.7 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.0(16) . . ? C10 C9 C2 119.5(16) . . ? C14 C9 C2 122.4(14) . . ? C9 C10 C11 119.3(18) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 121.6(17) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C13 C12 C11 118.3(17) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 119.7(19) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C9 123.0(18) . . ? C13 C14 H14 118.5 . . ? C9 C14 H14 118.5 . . ? N3 C15 C16 123.2(15) . . ? N3 C15 H15 118.4 . . ? C16 C15 H15 118.4 . . ? C15 C16 C17 119.5(16) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C18 C17 C16 116.8(15) . . ? C18 C17 H17 121.6 . . ? C16 C17 H17 121.6 . . ? C19 C18 C17 120.7(14) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 N3 121.2(14) . . ? C18 C19 H19 119.4 . . ? N3 C19 H19 119.4 . . ? C21 C20 N5 104.6(13) . . ? C21 C20 Pd2 132.2(11) . . ? N5 C20 Pd2 123.1(10) . . ? C20 C21 N4 108.5(13) . . ? C20 C21 C28 129.7(14) . . ? N4 C21 C28 121.8(13) . . ? N4 C22 N5 108.7(13) . . ? N4 C22 C23 131.5(14) . . ? N5 C22 C23 119.8(13) . . ? C24 C23 C22 115.7(14) . . ? C24 C23 H23 122.2 . . ? C22 C23 H23 122.2 . . ? C25 C24 C23 124.5(17) . . ? C25 C24 H24 117.8 . . ? C23 C24 H24 117.8 . . ? C24 C25 C26 120.5(16) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 N5 116.7(14) . . ? C25 C26 H26 121.6 . . ? N5 C26 H26 121.6 . . ? N4 C27 H27A 109.5 . . ? N4 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N4 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C33 119.3(14) . . ? C29 C28 C21 119.8(15) . . ? C33 C28 C21 120.8(13) . . ? C28 C29 C30 119.5(17) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C29 C30 C31 118.8(16) . . ? C29 C30 H30 120.6 . . ? C31 C30 H30 120.6 . . ? C32 C31 C30 120.4(16) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C31 C32 C33 121.0(17) . . ? C31 C32 H32 119.5 . . ? C33 C32 H32 119.5 . . ? C28 C33 C32 120.8(14) . . ? C28 C33 H33 119.6 . . ? C32 C33 H33 119.6 . . ? N6 C34 C35 122.7(14) . . ? N6 C34 H34 118.7 . . ? C35 C34 H34 118.7 . . ? C34 C35 C36 117.7(13) . . ? C34 C35 H35 121.2 . . ? C36 C35 H35 121.2 . . ? C37 C36 C35 118.1(15) . . ? C37 C36 H36 121.0 . . ? C35 C36 H36 121.0 . . ? C36 C37 C38 121.1(17) . . ? C36 C37 H37 119.4 . . ? C38 C37 H37 119.4 . . ? N6 C38 C37 121.2(16) . . ? N6 C38 H38 119.4 . . ? C37 C38 H38 119.4 . . ? 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 C1 Pd1 N3 C15 -39(5) . . . . ? I2 Pd1 N3 C15 -124.9(12) . . . . ? I1 Pd1 N3 C15 60.1(12) . . . . ? C1 Pd1 N3 C19 137(5) . . . . ? I2 Pd1 N3 C19 50.9(11) . . . . ? I1 Pd1 N3 C19 -124.0(11) . . . . ? C20 Pd2 N6 C34 -126(5) . . . . ? I3 Pd2 N6 C34 -67.0(12) . . . . ? I4 Pd2 N6 C34 104.9(12) . . . . ? C20 Pd2 N6 C38 50(6) . . . . ? I3 Pd2 N6 C38 109.1(12) . . . . ? I4 Pd2 N6 C38 -79.0(12) . . . . ? C3 N2 C1 C2 1.9(17) . . . . ? C7 N2 C1 C2 178.6(14) . . . . ? C3 N2 C1 Pd1 -178.3(11) . . . . ? C7 N2 C1 Pd1 -1(2) . . . . ? N3 Pd1 C1 C2 12(6) . . . . ? I2 Pd1 C1 C2 98.7(14) . . . . ? I1 Pd1 C1 C2 -86.8(14) . . . . ? N3 Pd1 C1 N2 -168(4) . . . . ? I2 Pd1 C1 N2 -81.1(13) . . . . ? I1 Pd1 C1 N2 93.4(13) . . . . ? N2 C1 C2 N1 -1.9(18) . . . . ? Pd1 C1 C2 N1 178.3(11) . . . . ? N2 C1 C2 C9 -178.5(16) . . . . ? Pd1 C1 C2 C9 2(3) . . . . ? C3 N1 C2 C1 1.3(18) . . . . ? C8 N1 C2 C1 177.5(14) . . . . ? C3 N1 C2 C9 178.4(14) . . . . ? C8 N1 C2 C9 -5(3) . . . . ? C2 N1 C3 N2 -0.2(17) . . . . ? C8 N1 C3 N2 -176.6(13) . . . . ? C2 N1 C3 C4 -178.7(17) . . . . ? C8 N1 C3 C4 5(3) . . . . ? C1 N2 C3 N1 -1.0(17) . . . . ? C7 N2 C3 N1 -178.1(13) . . . . ? C1 N2 C3 C4 177.7(14) . . . . ? C7 N2 C3 C4 1(2) . . . . ? N1 C3 C4 C5 178.1(16) . . . . ? N2 C3 C4 C5 0(2) . . . . ? C3 C4 C5 C6 2(3) . . . . ? C4 C5 C6 C7 -4(3) . . . . ? C5 C6 C7 N2 5(2) . . . . ? C3 N2 C7 C6 -3(2) . . . . ? C1 N2 C7 C6 -179.4(16) . . . . ? C1 C2 C9 C10 -65(2) . . . . ? N1 C2 C9 C10 118.9(16) . . . . ? C1 C2 C9 C14 112(2) . . . . ? N1 C2 C9 C14 -65(2) . . . . ? C14 C9 C10 C11 1.8(16) . . . . ? C2 C9 C10 C11 178.2(15) . . . . ? C9 C10 C11 C12 -1.0(17) . . . . ? C10 C11 C12 C13 0(2) . . . . ? C11 C12 C13 C14 0(3) . . . . ? C12 C13 C14 C9 1(3) . . . . ? C10 C9 C14 C13 -2(3) . . . . ? C2 C9 C14 C13 -178.0(18) . . . . ? C19 N3 C15 C16 -2(2) . . . . ? Pd1 N3 C15 C16 174.1(14) . . . . ? N3 C15 C16 C17 3(3) . . . . ? C15 C16 C17 C18 -3(2) . . . . ? C16 C17 C18 C19 2(2) . . . . ? C17 C18 C19 N3 -2(2) . . . . ? C15 N3 C19 C18 1(2) . . . . ? Pd1 N3 C19 C18 -174.6(11) . . . . ? C22 N5 C20 C21 0.9(16) . . . . ? C26 N5 C20 C21 179.8(14) . . . . ? C22 N5 C20 Pd2 -176.3(10) . . . . ? C26 N5 C20 Pd2 3(2) . . . . ? N6 Pd2 C20 C21 -39(6) . . . . ? I3 Pd2 C20 C21 -97.7(15) . . . . ? I4 Pd2 C20 C21 90.7(15) . . . . ? N6 Pd2 C20 N5 138(5) . . . . ? I3 Pd2 C20 N5 78.7(11) . . . . ? I4 Pd2 C20 N5 -93.0(11) . . . . ? N5 C20 C21 N4 -2.3(16) . . . . ? Pd2 C20 C21 N4 174.5(11) . . . . ? N5 C20 C21 C28 178.1(15) . . . . ? Pd2 C20 C21 C28 -5(3) . . . . ? C22 N4 C21 C20 3.1(17) . . . . ? C27 N4 C21 C20 174.2(15) . . . . ? C22 N4 C21 C28 -177.3(14) . . . . ? C27 N4 C21 C28 -6(2) . . . . ? C21 N4 C22 N5 -2.4(16) . . . . ? C27 N4 C22 N5 -173.6(14) . . . . ? C21 N4 C22 C23 179.2(16) . . . . ? C27 N4 C22 C23 8(3) . . . . ? C26 N5 C22 N4 -178.0(13) . . . . ? C20 N5 C22 N4 1.0(17) . . . . ? C26 N5 C22 C23 1(2) . . . . ? C20 N5 C22 C23 179.7(13) . . . . ? N4 C22 C23 C24 179.7(16) . . . . ? N5 C22 C23 C24 1(2) . . . . ? C22 C23 C24 C25 -4(2) . . . . ? C23 C24 C25 C26 4(3) . . . . ? C24 C25 C26 N5 -2(2) . . . . ? C22 N5 C26 C25 -1(2) . . . . ? C20 N5 C26 C25 -179.3(14) . . . . ? C20 C21 C28 C29 124.9(18) . . . . ? N4 C21 C28 C29 -55(2) . . . . ? C20 C21 C28 C33 -59(2) . . . . ? N4 C21 C28 C33 121.9(16) . . . . ? C33 C28 C29 C30 5(2) . . . . ? C21 C28 C29 C30 -178.8(16) . . . . ? C28 C29 C30 C31 -3(3) . . . . ? C29 C30 C31 C32 -1(3) . . . . ? C30 C31 C32 C33 3(3) . . . . ? C29 C28 C33 C32 -2(2) . . . . ? C21 C28 C33 C32 -179.0(14) . . . . ? C31 C32 C33 C28 -2(2) . . . . ? C38 N6 C34 C35 -2(2) . . . . ? Pd2 N6 C34 C35 174.3(11) . . . . ? N6 C34 C35 C36 0(2) . . . . ? C34 C35 C36 C37 1(2) . . . . ? C35 C36 C37 C38 0(3) . . . . ? C34 N6 C38 C37 3(3) . . . . ? Pd2 N6 C38 C37 -173.6(14) . . . . ? C36 C37 C38 N6 -2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.642 _refine_diff_density_min -1.800 _refine_diff_density_rms 0.284 #===END data_pg219 _database_code_depnum_ccdc_archive 'CCDC 698778' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 I2 N3 Pd' _chemical_formula_weight 675.61 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' I I -0.4742 1.8119 '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 21/n' 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 13.2678(14) _cell_length_b 9.3838(11) _cell_length_c 17.6375(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.558(9) _cell_angle_gamma 90.00 _cell_volume 2181.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5453 _cell_measurement_theta_min 2.9499 _cell_measurement_theta_max 33.1734 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.057 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 3.692 _exptl_absorpt_correction_T_min 0.6454 _exptl_absorpt_correction_T_max 0.8369 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16861 _diffrn_reflns_av_R_equivalents 0.0991 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3822 _reflns_number_gt 3267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0705P)^2^+17.2665P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3822 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1364 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 Pd1 Pd 0.25680(4) 0.83449(5) 0.41068(3) 0.02294(19) Uani 1 1 d . . . I1 I 0.07210(4) 0.91530(6) 0.42009(4) 0.0369(2) Uani 1 1 d . . . I2 I 0.43542(4) 0.73332(6) 0.39435(3) 0.0371(2) Uani 1 1 d . . . N1 N 0.1493(5) 0.5551(6) 0.4047(4) 0.0248(13) Uani 1 1 d . . . N2 N 0.1730(5) 0.4581(7) 0.5172(4) 0.0266(14) Uani 1 1 d . . . N3 N 0.2967(5) 1.0440(7) 0.3802(4) 0.0256(14) Uani 1 1 d . . . C1 C 0.2158(6) 0.6469(8) 0.4478(4) 0.0258(16) Uani 1 1 d . . . C2 C 0.1238(6) 0.4415(8) 0.4485(5) 0.0253(16) Uani 1 1 d . . . C3 C 0.2300(6) 0.5856(8) 0.5187(5) 0.0286(17) Uani 1 1 d . . . C4 C 0.1095(6) 0.5664(8) 0.3294(4) 0.0270(16) Uani 1 1 d . . . H4 H 0.1283 0.6437 0.2991 0.032 Uiso 1 1 calc R . . C5 C 0.0436(6) 0.4671(8) 0.2990(5) 0.0315(18) Uani 1 1 d . . . H5 H 0.0180 0.4738 0.2466 0.038 Uiso 1 1 calc R . . C6 C 0.0110(7) 0.3511(8) 0.3435(5) 0.0346(19) Uani 1 1 d . . . C7 C -0.0644(8) 0.2468(10) 0.3071(6) 0.042(2) Uani 1 1 d . . . H7A H -0.0755 0.1714 0.3437 0.063 Uiso 1 1 calc R . . H7B H -0.0386 0.2047 0.2622 0.063 Uiso 1 1 calc R . . H7C H -0.1286 0.2957 0.2913 0.063 Uiso 1 1 calc R . . C8 C 0.0534(6) 0.3396(8) 0.4172(5) 0.0287(17) Uani 1 1 d . . . H8 H 0.0354 0.2623 0.4477 0.034 Uiso 1 1 calc R . . C9 C 0.1582(6) 0.3650(8) 0.5823(5) 0.0314(18) Uani 1 1 d . . . H9A H 0.0849 0.3450 0.5822 0.038 Uiso 1 1 calc R . . H9B H 0.1820 0.4150 0.6305 0.038 Uiso 1 1 calc R . . C10 C 0.2166(8) 0.2220(9) 0.5789(6) 0.043(2) Uani 1 1 d . . . H10A H 0.1929 0.1721 0.5314 0.064 Uiso 1 1 calc R . . H10B H 0.2043 0.1625 0.6225 0.064 Uiso 1 1 calc R . . H10C H 0.2894 0.2414 0.5806 0.064 Uiso 1 1 calc R . . C11 C 0.2905(6) 0.6404(8) 0.5869(5) 0.0286(17) Uani 1 1 d . . . C12 C 0.3522(7) 0.5519(9) 0.6363(5) 0.0349(19) Uani 1 1 d . . . H12 H 0.3582 0.4536 0.6246 0.042 Uiso 1 1 calc R . . C13 C 0.4047(7) 0.6069(9) 0.7026(5) 0.039(2) Uani 1 1 d . . . H13 H 0.4472 0.5459 0.7352 0.047 Uiso 1 1 calc R . . C14 C 0.3965(7) 0.7454(11) 0.7213(5) 0.042(2) Uani 1 1 d . . . H14 H 0.4301 0.7805 0.7680 0.051 Uiso 1 1 calc R . . C15 C 0.3377(8) 0.8378(10) 0.6709(6) 0.044(2) Uani 1 1 d . . . H15 H 0.3334 0.9362 0.6829 0.052 Uiso 1 1 calc R . . C16 C 0.2861(7) 0.7852(9) 0.6041(5) 0.036(2) Uani 1 1 d . . . H16 H 0.2475 0.8479 0.5699 0.043 Uiso 1 1 calc R . . C17 C 0.3729(7) 1.1115(10) 0.4198(5) 0.038(2) Uani 1 1 d . . . H17 H 0.4144 1.0603 0.4580 0.046 Uiso 1 1 calc R . . C18 C 0.3950(8) 1.2537(9) 0.4080(6) 0.044(2) Uani 1 1 d . . . H18 H 0.4478 1.3000 0.4397 0.053 Uiso 1 1 calc R . . C19 C 0.3402(7) 1.3259(9) 0.3505(5) 0.040(2) Uani 1 1 d . . . H19 H 0.3554 1.4226 0.3406 0.047 Uiso 1 1 calc R . . C20 C 0.2620(6) 1.2567(8) 0.3066(5) 0.0307(18) Uani 1 1 d . . . H20 H 0.2225 1.3044 0.2659 0.037 Uiso 1 1 calc R . . C21 C 0.2430(6) 1.1162(8) 0.3235(5) 0.0280(17) Uani 1 1 d . . . H21 H 0.1892 1.0683 0.2936 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.0273(3) 0.0118(3) 0.0303(3) 0.0024(2) 0.0052(2) -0.0012(2) I1 0.0350(3) 0.0213(3) 0.0562(4) 0.0006(2) 0.0124(3) 0.0003(2) I2 0.0328(3) 0.0298(3) 0.0488(4) 0.0022(2) 0.0051(3) 0.0040(2) N1 0.031(3) 0.016(3) 0.029(3) -0.002(3) 0.007(3) 0.003(3) N2 0.033(3) 0.014(3) 0.033(4) 0.004(3) 0.007(3) -0.004(3) N3 0.031(3) 0.018(3) 0.028(3) 0.002(3) 0.003(3) 0.001(3) C1 0.029(4) 0.018(4) 0.029(4) -0.002(3) -0.002(3) -0.002(3) C2 0.024(4) 0.015(3) 0.037(4) 0.002(3) 0.005(3) 0.000(3) C3 0.032(4) 0.016(4) 0.038(4) -0.002(3) 0.004(4) -0.004(3) C4 0.036(4) 0.017(4) 0.029(4) 0.000(3) 0.005(3) 0.001(3) C5 0.038(4) 0.021(4) 0.036(4) -0.005(3) 0.006(4) 0.000(3) C6 0.039(5) 0.020(4) 0.045(5) -0.011(4) 0.006(4) -0.005(4) C7 0.049(5) 0.028(4) 0.048(5) -0.004(4) 0.004(4) -0.014(4) C8 0.036(4) 0.015(4) 0.037(4) -0.003(3) 0.011(4) 0.001(3) C9 0.034(4) 0.021(4) 0.040(5) 0.009(3) 0.006(4) -0.001(3) C10 0.059(6) 0.017(4) 0.050(5) 0.008(4) -0.003(5) -0.003(4) C11 0.030(4) 0.024(4) 0.033(4) 0.002(3) 0.009(3) -0.003(3) C12 0.042(5) 0.019(4) 0.043(5) 0.006(3) 0.002(4) -0.005(4) C13 0.042(5) 0.028(4) 0.046(5) 0.005(4) -0.005(4) -0.004(4) C14 0.040(5) 0.050(6) 0.034(5) 0.003(4) -0.007(4) -0.005(4) C15 0.054(6) 0.026(5) 0.048(5) -0.007(4) -0.004(5) -0.001(4) C16 0.047(5) 0.023(4) 0.037(5) -0.001(4) 0.001(4) 0.005(4) C17 0.039(5) 0.038(5) 0.036(5) 0.008(4) -0.002(4) -0.006(4) C18 0.050(6) 0.028(4) 0.053(6) -0.004(4) -0.003(5) -0.024(4) C19 0.048(5) 0.021(4) 0.052(5) 0.009(4) 0.015(4) 0.000(4) C20 0.037(5) 0.024(4) 0.032(4) 0.004(3) 0.009(4) 0.009(3) C21 0.031(4) 0.021(4) 0.033(4) 0.003(3) 0.005(3) 0.001(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 C1 1.976(8) . ? Pd1 N3 2.121(6) . ? Pd1 I1 2.5887(8) . ? Pd1 I2 2.5993(8) . ? N1 C4 1.376(10) . ? N1 C2 1.381(10) . ? N1 C1 1.395(10) . ? N2 C2 1.318(10) . ? N2 C3 1.413(10) . ? N2 C9 1.474(10) . ? N3 C17 1.323(11) . ? N3 C21 1.344(10) . ? C1 C3 1.370(11) . ? C2 C8 1.405(11) . ? C3 C11 1.462(11) . ? C4 C5 1.346(11) . ? C4 H4 0.9500 . ? C5 C6 1.437(12) . ? C5 H5 0.9500 . ? C6 C8 1.361(12) . ? C6 C7 1.492(11) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8 0.9500 . ? C9 C10 1.554(12) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.395(11) . ? C11 C12 1.399(11) . ? C12 C13 1.390(12) . ? C12 H12 0.9500 . ? C13 C14 1.348(14) . ? C13 H13 0.9500 . ? C14 C15 1.412(13) . ? C14 H14 0.9500 . ? C15 C16 1.384(12) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.387(12) . ? C17 H17 0.9500 . ? C18 C19 1.359(13) . ? C18 H18 0.9500 . ? C19 C20 1.384(13) . ? C19 H19 0.9500 . ? C20 C21 1.381(11) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? 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 C1 Pd1 N3 174.7(3) . . ? C1 Pd1 I1 86.6(2) . . ? N3 Pd1 I1 90.59(18) . . ? C1 Pd1 I2 90.0(2) . . ? N3 Pd1 I2 93.05(18) . . ? I1 Pd1 I2 174.79(3) . . ? C4 N1 C2 120.6(6) . . ? C4 N1 C1 128.8(7) . . ? C2 N1 C1 110.6(6) . . ? C2 N2 C3 108.9(6) . . ? C2 N2 C9 123.4(6) . . ? C3 N2 C9 127.3(7) . . ? C17 N3 C21 117.4(7) . . ? C17 N3 Pd1 120.5(5) . . ? C21 N3 Pd1 121.9(5) . . ? C3 C1 N1 104.5(7) . . ? C3 C1 Pd1 131.5(6) . . ? N1 C1 Pd1 123.4(5) . . ? N2 C2 N1 107.2(6) . . ? N2 C2 C8 132.7(7) . . ? N1 C2 C8 120.0(7) . . ? C1 C3 N2 108.7(7) . . ? C1 C3 C11 127.5(7) . . ? N2 C3 C11 123.7(7) . . ? C5 C4 N1 119.4(7) . . ? C5 C4 H4 120.3 . . ? N1 C4 H4 120.3 . . ? C4 C5 C6 121.9(8) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C8 C6 C5 117.7(7) . . ? C8 C6 C7 122.9(8) . . ? C5 C6 C7 119.4(8) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 C2 120.3(8) . . ? C6 C8 H8 119.8 . . ? C2 C8 H8 119.8 . . ? N2 C9 C10 111.7(7) . . ? N2 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? N2 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 118.6(8) . . ? C16 C11 C3 119.3(7) . . ? C12 C11 C3 122.1(7) . . ? C13 C12 C11 120.3(8) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 121.2(8) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 119.5(9) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.0(8) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.2(8) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? N3 C17 C18 122.9(8) . . ? N3 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C19 C18 C17 119.2(8) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 119.1(8) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C21 C20 C19 118.1(8) . . ? C21 C20 H20 120.9 . . ? C19 C20 H20 120.9 . . ? N3 C21 C20 123.2(8) . . ? N3 C21 H21 118.4 . . ? C20 C21 H21 118.4 . . ? 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 C1 Pd1 N3 C17 67(3) . . . . ? I1 Pd1 N3 C17 124.9(7) . . . . ? I2 Pd1 N3 C17 -58.8(7) . . . . ? C1 Pd1 N3 C21 -109(3) . . . . ? I1 Pd1 N3 C21 -51.2(6) . . . . ? I2 Pd1 N3 C21 125.1(6) . . . . ? C4 N1 C1 C3 179.6(7) . . . . ? C2 N1 C1 C3 0.1(9) . . . . ? C4 N1 C1 Pd1 7.6(11) . . . . ? C2 N1 C1 Pd1 -171.8(5) . . . . ? N3 Pd1 C1 C3 -42(3) . . . . ? I1 Pd1 C1 C3 -100.4(8) . . . . ? I2 Pd1 C1 C3 83.6(8) . . . . ? N3 Pd1 C1 N1 127(3) . . . . ? I1 Pd1 C1 N1 69.2(6) . . . . ? I2 Pd1 C1 N1 -106.8(6) . . . . ? C3 N2 C2 N1 1.0(8) . . . . ? C9 N2 C2 N1 174.2(7) . . . . ? C3 N2 C2 C8 -176.1(8) . . . . ? C9 N2 C2 C8 -2.9(13) . . . . ? C4 N1 C2 N2 179.7(7) . . . . ? C1 N1 C2 N2 -0.7(8) . . . . ? C4 N1 C2 C8 -2.7(11) . . . . ? C1 N1 C2 C8 176.8(7) . . . . ? N1 C1 C3 N2 0.5(9) . . . . ? Pd1 C1 C3 N2 171.6(6) . . . . ? N1 C1 C3 C11 -177.8(8) . . . . ? Pd1 C1 C3 C11 -6.8(14) . . . . ? C2 N2 C3 C1 -1.0(9) . . . . ? C9 N2 C3 C1 -173.8(7) . . . . ? C2 N2 C3 C11 177.4(8) . . . . ? C9 N2 C3 C11 4.6(12) . . . . ? C2 N1 C4 C5 1.3(11) . . . . ? C1 N1 C4 C5 -178.1(8) . . . . ? N1 C4 C5 C6 1.9(12) . . . . ? C4 C5 C6 C8 -3.7(12) . . . . ? C4 C5 C6 C7 178.3(8) . . . . ? C5 C6 C8 C2 2.2(12) . . . . ? C7 C6 C8 C2 -179.8(8) . . . . ? N2 C2 C8 C6 177.6(8) . . . . ? N1 C2 C8 C6 0.9(12) . . . . ? C2 N2 C9 C10 79.3(9) . . . . ? C3 N2 C9 C10 -108.9(9) . . . . ? C1 C3 C11 C16 42.2(13) . . . . ? N2 C3 C11 C16 -135.9(9) . . . . ? C1 C3 C11 C12 -138.6(9) . . . . ? N2 C3 C11 C12 43.3(12) . . . . ? C16 C11 C12 C13 2.3(13) . . . . ? C3 C11 C12 C13 -176.8(8) . . . . ? C11 C12 C13 C14 1.0(15) . . . . ? C12 C13 C14 C15 -3.2(15) . . . . ? C13 C14 C15 C16 2.2(16) . . . . ? C14 C15 C16 C11 1.1(15) . . . . ? C12 C11 C16 C15 -3.3(14) . . . . ? C3 C11 C16 C15 175.8(9) . . . . ? C21 N3 C17 C18 3.9(14) . . . . ? Pd1 N3 C17 C18 -172.4(8) . . . . ? N3 C17 C18 C19 -3.9(16) . . . . ? C17 C18 C19 C20 1.8(15) . . . . ? C18 C19 C20 C21 0.1(13) . . . . ? C17 N3 C21 C20 -1.8(12) . . . . ? Pd1 N3 C21 C20 174.4(6) . . . . ? C19 C20 C21 N3 -0.1(13) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 3.257 _refine_diff_density_min -1.191 _refine_diff_density_rms 0.229 #===END #===END data_pg220 _database_code_depnum_ccdc_archive 'CCDC 698779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 I2 N3 Pd' _chemical_formula_weight 675.61 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' I I -0.4742 1.8119 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4796(10) _cell_length_b 10.0617(13) _cell_length_c 12.5813(17) _cell_angle_alpha 80.090(11) _cell_angle_beta 69.351(11) _cell_angle_gamma 74.071(10) _cell_volume 1076.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5948 _cell_measurement_theta_min 3.3458 _cell_measurement_theta_max 32.4780 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.085 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 3.742 _exptl_absorpt_correction_T_min 0.3715 _exptl_absorpt_correction_T_max 0.4932 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7838 _diffrn_reflns_av_R_equivalents 0.0738 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3767 _reflns_number_gt 3374 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.1305P)^2^+7.6855P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3767 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1993 _refine_ls_wR_factor_gt 0.1847 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 0.0752(9) 0.2385(10) 0.2673(7) 0.0208(17) Uani 1 1 d . . . C2 C 0.0064(9) 0.1297(9) 0.3049(7) 0.0184(16) Uani 1 1 d . . . C3 C -0.1854(9) 0.3194(9) 0.3323(7) 0.0197(17) Uani 1 1 d . . . C4 C -0.0387(11) 0.4955(9) 0.2596(7) 0.0235(18) Uani 1 1 d . . . H4 H 0.0585 0.5201 0.2271 0.028 Uiso 1 1 calc R . . C5 C -0.1729(11) 0.5946(10) 0.2830(7) 0.028(2) Uani 1 1 d . . . C6 C -0.1655(13) 0.7454(10) 0.2597(9) 0.035(2) Uani 1 1 d . . . H6A H -0.1913 0.7851 0.3320 0.053 Uiso 1 1 calc R . . H6B H -0.2398 0.7962 0.2206 0.053 Uiso 1 1 calc R . . H6C H -0.0606 0.7526 0.2115 0.053 Uiso 1 1 calc R . . C7 C -0.3160(11) 0.5550(10) 0.3291(8) 0.031(2) Uani 1 1 d . . . H7 H -0.4094 0.6251 0.3426 0.037 Uiso 1 1 calc R . . C8 C -0.2798(10) 0.1059(10) 0.3904(8) 0.0249(18) Uani 1 1 d . . . H8A H -0.2357 0.0076 0.3738 0.030 Uiso 1 1 calc R . . H8B H -0.3573 0.1455 0.3505 0.030 Uiso 1 1 calc R . . C9 C -0.3606(11) 0.1127(10) 0.5182(8) 0.031(2) Uani 1 1 d . . . H9A H -0.2842 0.0756 0.5582 0.046 Uiso 1 1 calc R . . H9B H -0.4391 0.0576 0.5440 0.046 Uiso 1 1 calc R . . H9C H -0.4106 0.2093 0.5348 0.046 Uiso 1 1 calc R . . C10 C 0.0806(9) -0.0204(9) 0.3067(7) 0.0207(17) Uani 1 1 d . . . C11 C 0.0340(10) -0.1154(9) 0.3978(7) 0.0210(17) Uani 1 1 d . . . H11 H -0.0519 -0.0848 0.4626 0.025 Uiso 1 1 calc R . . C12 C 0.1103(11) -0.2540(10) 0.3962(8) 0.029(2) Uani 1 1 d . . . H12 H 0.0766 -0.3180 0.4591 0.035 Uiso 1 1 calc R . . C13 C 0.2358(12) -0.2987(11) 0.3026(9) 0.038(2) Uani 1 1 d . . . H13 H 0.2896 -0.3935 0.3015 0.046 Uiso 1 1 calc R . . C013 C -0.3245(10) 0.4213(9) 0.3547(8) 0.0250(18) Uani 1 1 d . . . H013 H -0.4218 0.3967 0.3869 0.030 Uiso 1 1 calc R . . C14 C 0.2836(12) -0.2048(11) 0.2096(9) 0.041(3) Uani 1 1 d . . . H14 H 0.3690 -0.2358 0.1447 0.049 Uiso 1 1 calc R . . C15 C 0.2073(11) -0.0683(9) 0.2121(8) 0.0267(19) Uani 1 1 d . . . H15 H 0.2408 -0.0048 0.1487 0.032 Uiso 1 1 calc R . . C16 C 0.6312(12) 0.1156(12) 0.1150(9) 0.038(2) Uani 1 1 d . . . H16 H 0.5898 0.0363 0.1271 0.045 Uiso 1 1 calc R . . C17 C 0.7885(13) 0.0992(15) 0.0812(10) 0.052(3) Uani 1 1 d . . . H17 H 0.8538 0.0087 0.0720 0.062 Uiso 1 1 calc R . . C18 C 0.8532(12) 0.2107(14) 0.0604(10) 0.045(3) Uani 1 1 d . . . H18 H 0.9623 0.2003 0.0357 0.054 Uiso 1 1 calc R . . C19 C 0.7553(14) 0.3348(14) 0.0767(10) 0.046(3) Uani 1 1 d . . . H19 H 0.7958 0.4148 0.0639 0.055 Uiso 1 1 calc R . . C20 C 0.5957(12) 0.3499(13) 0.1120(9) 0.042(3) Uani 1 1 d . . . H20 H 0.5294 0.4400 0.1223 0.050 Uiso 1 1 calc R . . Pd1 Pd 0.29556(7) 0.24913(7) 0.19939(5) 0.0197(2) Uani 1 1 d . . . I1 I 0.27724(8) 0.26516(8) -0.00310(5) 0.0379(3) Uani 1 1 d . . . I2 I 0.29028(7) 0.28867(6) 0.39917(5) 0.0291(3) Uani 1 1 d . . . N1 N -0.0467(8) 0.3567(8) 0.2845(6) 0.0208(15) Uani 1 1 d . . . N2 N -0.1555(8) 0.1810(7) 0.3458(6) 0.0179(14) Uani 1 1 d . . . N3 N 0.5342(8) 0.2405(8) 0.1316(6) 0.0237(15) 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 0.012(4) 0.030(5) 0.018(4) -0.004(3) -0.006(3) 0.002(3) C2 0.015(4) 0.016(4) 0.022(4) -0.004(3) -0.008(3) 0.005(3) C3 0.014(4) 0.023(4) 0.022(4) -0.002(3) -0.006(3) -0.004(3) C4 0.030(5) 0.012(4) 0.025(4) -0.005(3) -0.011(4) 0.005(3) C5 0.030(5) 0.032(5) 0.021(4) -0.011(4) -0.012(4) 0.006(4) C6 0.048(6) 0.019(5) 0.040(5) -0.010(4) -0.027(5) 0.012(4) C7 0.024(5) 0.033(5) 0.032(5) -0.012(4) -0.013(4) 0.010(4) C8 0.014(4) 0.025(5) 0.034(5) -0.007(4) -0.008(3) 0.000(3) C9 0.020(4) 0.027(5) 0.036(5) -0.006(4) -0.010(4) 0.011(4) C10 0.016(4) 0.015(4) 0.031(4) -0.008(3) -0.011(3) 0.005(3) C11 0.019(4) 0.018(4) 0.025(4) -0.002(3) -0.007(3) -0.002(3) C12 0.027(5) 0.025(5) 0.035(5) -0.005(4) -0.012(4) -0.001(4) C13 0.038(6) 0.021(5) 0.053(6) -0.012(4) -0.020(5) 0.009(4) C013 0.024(4) 0.016(4) 0.034(5) -0.006(3) -0.008(4) -0.002(4) C14 0.037(6) 0.027(5) 0.040(6) -0.012(4) 0.001(5) 0.009(5) C15 0.025(5) 0.017(4) 0.031(5) 0.001(4) -0.004(4) -0.002(4) C16 0.026(5) 0.037(6) 0.041(6) -0.011(5) -0.004(4) 0.003(4) C17 0.030(6) 0.062(8) 0.042(6) -0.007(6) -0.006(5) 0.017(6) C18 0.022(5) 0.065(8) 0.046(6) -0.019(6) -0.004(4) -0.010(5) C19 0.045(7) 0.058(8) 0.042(6) -0.008(5) -0.011(5) -0.024(6) C20 0.030(5) 0.051(7) 0.040(6) -0.021(5) -0.007(4) 0.006(5) Pd1 0.0132(4) 0.0201(4) 0.0227(4) -0.0042(3) -0.0062(3) 0.0029(3) I1 0.0351(4) 0.0491(5) 0.0303(4) -0.0058(3) -0.0112(3) -0.0087(3) I2 0.0237(4) 0.0348(4) 0.0283(4) -0.0023(3) -0.0105(3) -0.0035(3) N1 0.020(4) 0.020(4) 0.021(3) -0.007(3) -0.009(3) 0.004(3) N2 0.014(3) 0.010(3) 0.029(4) -0.001(3) -0.008(3) -0.001(3) N3 0.020(4) 0.025(4) 0.026(4) -0.003(3) -0.006(3) -0.005(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 C1 C2 1.358(13) . ? C1 N1 1.398(11) . ? C1 Pd1 1.984(8) . ? C2 N2 1.410(10) . ? C2 C10 1.481(11) . ? C3 N2 1.335(11) . ? C3 N1 1.366(11) . ? C3 C013 1.402(12) . ? C4 C5 1.356(13) . ? C4 N1 1.395(11) . ? C4 H4 0.9500 . ? C5 C7 1.414(14) . ? C5 C6 1.511(14) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C013 1.346(14) . ? C7 H7 0.9500 . ? C8 N2 1.466(11) . ? C8 C9 1.522(13) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.386(12) . ? C10 C15 1.401(12) . ? C11 C12 1.384(13) . ? C11 H11 0.9500 . ? C12 C13 1.380(14) . ? C12 H12 0.9500 . ? C13 C14 1.396(15) . ? C13 H13 0.9500 . ? C013 H013 0.9500 . ? C14 C15 1.365(14) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 N3 1.338(13) . ? C16 C17 1.369(16) . ? C16 H16 0.9500 . ? C17 C18 1.366(19) . ? C17 H17 0.9500 . ? C18 C19 1.334(19) . ? C18 H18 0.9500 . ? C19 C20 1.391(16) . ? C19 H19 0.9500 . ? C20 N3 1.331(15) . ? C20 H20 0.9500 . ? Pd1 N3 2.100(7) . ? Pd1 I1 2.5887(9) . ? Pd1 I2 2.5929(8) . ? 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 C2 C1 N1 105.2(7) . . ? C2 C1 Pd1 132.4(6) . . ? N1 C1 Pd1 122.4(6) . . ? C1 C2 N2 108.9(7) . . ? C1 C2 C10 128.4(8) . . ? N2 C2 C10 122.7(7) . . ? N2 C3 N1 107.6(7) . . ? N2 C3 C013 132.2(8) . . ? N1 C3 C013 120.1(8) . . ? C5 C4 N1 118.5(9) . . ? C5 C4 H4 120.8 . . ? N1 C4 H4 120.8 . . ? C4 C5 C7 119.6(9) . . ? C4 C5 C6 118.9(9) . . ? C7 C5 C6 121.5(9) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C013 C7 C5 122.2(9) . . ? C013 C7 H7 118.9 . . ? C5 C7 H7 118.9 . . ? N2 C8 C9 112.9(7) . . ? N2 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N2 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 118.3(8) . . ? C11 C10 C2 123.7(7) . . ? C15 C10 C2 118.1(8) . . ? C12 C11 C10 121.2(8) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 119.6(9) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.1(9) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C7 C013 C3 117.9(8) . . ? C7 C013 H013 121.0 . . ? C3 C013 H013 121.0 . . ? C15 C14 C13 119.8(9) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C10 121.1(9) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? N3 C16 C17 121.7(11) . . ? N3 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C18 C17 C16 121.2(12) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 116.6(10) . . ? C19 C18 H18 121.7 . . ? C17 C18 H18 121.7 . . ? C18 C19 C20 121.7(12) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? N3 C20 C19 121.1(11) . . ? N3 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C1 Pd1 N3 174.7(3) . . ? C1 Pd1 I1 90.3(2) . . ? N3 Pd1 I1 91.0(2) . . ? C1 Pd1 I2 88.6(2) . . ? N3 Pd1 I2 91.27(19) . . ? I1 Pd1 I2 167.99(4) . . ? C3 N1 C4 121.6(7) . . ? C3 N1 C1 110.1(7) . . ? C4 N1 C1 128.3(7) . . ? C3 N2 C2 108.2(7) . . ? C3 N2 C8 121.9(7) . . ? C2 N2 C8 129.8(7) . . ? C20 N3 C16 117.7(9) . . ? C20 N3 Pd1 124.3(7) . . ? C16 N3 Pd1 117.8(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 C1 C2 N2 -0.7(9) . . . . ? Pd1 C1 C2 N2 179.9(6) . . . . ? N1 C1 C2 C10 179.9(7) . . . . ? Pd1 C1 C2 C10 0.5(13) . . . . ? N1 C4 C5 C7 -1.4(12) . . . . ? N1 C4 C5 C6 178.2(7) . . . . ? C4 C5 C7 C013 2.3(13) . . . . ? C6 C5 C7 C013 -177.2(8) . . . . ? C1 C2 C10 C11 137.3(9) . . . . ? N2 C2 C10 C11 -42.1(12) . . . . ? C1 C2 C10 C15 -41.1(12) . . . . ? N2 C2 C10 C15 139.6(8) . . . . ? C15 C10 C11 C12 0.2(12) . . . . ? C2 C10 C11 C12 -178.2(8) . . . . ? C10 C11 C12 C13 0.4(13) . . . . ? C11 C12 C13 C14 -1.0(15) . . . . ? C5 C7 C013 C3 -1.1(13) . . . . ? N2 C3 C013 C7 -178.6(9) . . . . ? N1 C3 C013 C7 -0.9(12) . . . . ? C12 C13 C14 C15 0.9(17) . . . . ? C13 C14 C15 C10 -0.3(17) . . . . ? C11 C10 C15 C14 -0.2(14) . . . . ? C2 C10 C15 C14 178.2(9) . . . . ? N3 C16 C17 C18 -1.4(18) . . . . ? C16 C17 C18 C19 1.1(18) . . . . ? C17 C18 C19 C20 -0.6(17) . . . . ? C18 C19 C20 N3 0.4(17) . . . . ? C2 C1 Pd1 N3 -10(4) . . . . ? N1 C1 Pd1 N3 171(3) . . . . ? C2 C1 Pd1 I1 94.1(8) . . . . ? N1 C1 Pd1 I1 -85.3(6) . . . . ? C2 C1 Pd1 I2 -97.9(8) . . . . ? N1 C1 Pd1 I2 82.8(6) . . . . ? N2 C3 N1 C4 -180.0(7) . . . . ? C013 C3 N1 C4 1.8(12) . . . . ? N2 C3 N1 C1 -0.2(9) . . . . ? C013 C3 N1 C1 -178.4(7) . . . . ? C5 C4 N1 C3 -0.6(12) . . . . ? C5 C4 N1 C1 179.6(8) . . . . ? C2 C1 N1 C3 0.5(9) . . . . ? Pd1 C1 N1 C3 -180.0(5) . . . . ? C2 C1 N1 C4 -179.7(7) . . . . ? Pd1 C1 N1 C4 -0.2(11) . . . . ? N1 C3 N2 C2 -0.2(9) . . . . ? C013 C3 N2 C2 177.7(9) . . . . ? N1 C3 N2 C8 -177.1(7) . . . . ? C013 C3 N2 C8 0.7(14) . . . . ? C1 C2 N2 C3 0.6(9) . . . . ? C10 C2 N2 C3 -180.0(7) . . . . ? C1 C2 N2 C8 177.2(8) . . . . ? C10 C2 N2 C8 -3.4(13) . . . . ? C9 C8 N2 C3 -74.4(10) . . . . ? C9 C8 N2 C2 109.4(9) . . . . ? C19 C20 N3 C16 -0.7(15) . . . . ? C19 C20 N3 Pd1 174.0(8) . . . . ? C17 C16 N3 C20 1.2(15) . . . . ? C17 C16 N3 Pd1 -173.9(8) . . . . ? C1 Pd1 N3 C20 -161(3) . . . . ? I1 Pd1 N3 C20 95.8(8) . . . . ? I2 Pd1 N3 C20 -72.4(8) . . . . ? C1 Pd1 N3 C16 14(3) . . . . ? I1 Pd1 N3 C16 -89.5(7) . . . . ? I2 Pd1 N3 C16 102.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.304 _refine_diff_density_min -2.355 _refine_diff_density_rms 0.321