# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Han Vinh Huynh' _publ_contact_author_email CHMHHV@NUS.EDU.SG _publ_section_title ; Mixed carbene-isocyanide Pd(II) complexes: synthesis, structures and reactivity towards nucleophiles ; loop_ _publ_author_name 'Han Vinh Huynh' 'Yuan Han' # Attachment '3.cif' data_5398 _database_code_depnum_ccdc_archive 'CCDC 703027' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H44 Br2 N4 Pd2' _chemical_formula_weight 809.29 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' Br Br -0.2901 2.4595 '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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 15.2383(6) _cell_length_b 23.7826(9) _cell_length_c 10.3642(4) _cell_angle_alpha 90.00 _cell_angle_beta 123.4320(10) _cell_angle_gamma 90.00 _cell_volume 3134.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 8429 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 27.51 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 3.720 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3177 _exptl_absorpt_correction_T_max 0.6240 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 16865 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7106 _reflns_number_gt 6617 _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^)+(0.0000P)^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 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 0.010(4) _refine_ls_number_reflns 7106 _refine_ls_number_parameters 325 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_gt 0.0199 _refine_ls_wR_factor_ref 0.0397 _refine_ls_wR_factor_gt 0.0393 _refine_ls_goodness_of_fit_ref 0.841 _refine_ls_restrained_S_all 0.841 _refine_ls_shift/su_max 0.004 _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 0.728093(14) 0.782330(9) 0.903322(19) 0.02400(5) Uani 1 1 d . . . Pd2 Pd 0.693500(15) 0.703807(9) 1.03415(2) 0.02373(5) Uani 1 1 d . . . Br1 Br 0.76356(2) 0.867740(13) 0.79317(3) 0.03767(8) Uani 1 1 d . . . Br2 Br 0.66352(2) 0.627498(12) 1.17571(3) 0.03700(8) Uani 1 1 d . . . N1 N 0.92248(19) 0.71894(10) 0.9521(3) 0.0312(5) Uani 1 1 d . . . N2 N 0.53288(17) 0.84220(9) 0.8585(2) 0.0281(5) Uani 1 1 d . . . N3 N 0.57849(19) 0.63052(10) 0.7371(3) 0.0336(6) Uani 1 1 d . . . N4 N 0.81422(19) 0.79126(10) 1.2978(3) 0.0331(6) Uani 1 1 d . . . C1 C 0.8509(2) 0.74078(12) 0.9376(3) 0.0304(6) Uani 1 1 d . . . C2 C 0.6028(2) 0.81730(11) 0.8765(3) 0.0265(6) Uani 1 1 d . . . C3 C 0.6192(2) 0.66042(12) 0.8406(3) 0.0287(6) Uani 1 1 d . . . C4 C 0.7718(2) 0.75756(12) 1.2051(3) 0.0282(6) Uani 1 1 d . . . C5 C 1.0131(2) 0.69214(12) 0.9653(3) 0.0314(6) Uani 1 1 d . . . H5 H 1.0553 0.6733 1.0671 0.038 Uiso 1 1 calc R . . C6 C 1.0805(2) 0.73623(13) 0.9547(4) 0.0401(7) Uani 1 1 d . . . H6A H 1.1474 0.7192 0.9826 0.048 Uiso 1 1 calc R . . H6B H 1.0962 0.7663 1.0291 0.048 Uiso 1 1 calc R . . C7 C 1.0268(3) 0.76144(14) 0.7930(4) 0.0492(9) Uani 1 1 d . . . H7A H 0.9646 0.7827 0.7698 0.059 Uiso 1 1 calc R . . H7B H 1.0750 0.7875 0.7891 0.059 Uiso 1 1 calc R . . C8 C 0.9943(3) 0.71571(15) 0.6728(4) 0.0541(9) Uani 1 1 d . . . H8A H 1.0570 0.6964 0.6913 0.065 Uiso 1 1 calc R . . H8B H 0.9579 0.7326 0.5696 0.065 Uiso 1 1 calc R . . C9 C 0.9221(3) 0.67357(15) 0.6799(4) 0.0483(8) Uani 1 1 d . . . H9A H 0.8570 0.6924 0.6534 0.058 Uiso 1 1 calc R . . H9B H 0.9037 0.6438 0.6037 0.058 Uiso 1 1 calc R . . C10 C 0.9739(2) 0.64795(13) 0.8385(4) 0.0407(7) Uani 1 1 d . . . H10A H 1.0334 0.6248 0.8586 0.049 Uiso 1 1 calc R . . H10B H 0.9235 0.6233 0.8414 0.049 Uiso 1 1 calc R . . C11 C 0.5363(2) 0.58454(12) 0.6251(3) 0.0312(7) Uani 1 1 d . . . H11 H 0.4597 0.5816 0.5786 0.037 Uiso 1 1 calc R . . C12 C 0.5550(2) 0.59686(14) 0.4981(3) 0.0421(8) Uani 1 1 d . . . H12A H 0.5178 0.5689 0.4156 0.051 Uiso 1 1 calc R . . H12B H 0.5262 0.6340 0.4538 0.051 Uiso 1 1 calc R . . C13 C 0.6700(3) 0.59564(16) 0.5582(4) 0.0550(9) Uani 1 1 d . . . H13A H 0.7054 0.6273 0.6290 0.066 Uiso 1 1 calc R . . H13B H 0.6785 0.5999 0.4717 0.066 Uiso 1 1 calc R . . C14 C 0.7211(3) 0.54056(16) 0.6430(4) 0.0582(10) Uani 1 1 d . . . H14A H 0.6915 0.5094 0.5690 0.070 Uiso 1 1 calc R . . H14B H 0.7968 0.5421 0.6865 0.070 Uiso 1 1 calc R . . C15 C 0.7042(2) 0.52959(13) 0.7717(4) 0.0469(8) Uani 1 1 d . . . H15A H 0.7340 0.4929 0.8187 0.056 Uiso 1 1 calc R . . H15B H 0.7406 0.5584 0.8518 0.056 Uiso 1 1 calc R . . C16 C 0.5888(2) 0.53033(12) 0.7102(3) 0.0403(7) Uani 1 1 d . . . H16A H 0.5799 0.5258 0.7964 0.048 Uiso 1 1 calc R . . H16B H 0.5543 0.4985 0.6398 0.048 Uiso 1 1 calc R . . C17 C 0.4512(2) 0.88194(11) 0.8299(3) 0.0283(6) Uani 1 1 d . . . H17 H 0.3964 0.8619 0.8356 0.034 Uiso 1 1 calc R . . C18 C 0.5000(2) 0.92740(13) 0.9532(3) 0.0364(7) Uani 1 1 d . . . H18A H 0.5384 0.9096 1.0554 0.044 Uiso 1 1 calc R . . H18B H 0.4438 0.9504 0.9453 0.044 Uiso 1 1 calc R . . C19 C 0.5750(2) 0.96556(12) 0.9393(3) 0.0396(7) Uani 1 1 d . . . H19A H 0.5987 0.9961 1.0149 0.048 Uiso 1 1 calc R . . H19B H 0.6369 0.9439 0.9631 0.048 Uiso 1 1 calc R . . C20 C 0.5224(2) 0.99032(12) 0.7779(4) 0.0403(7) Uani 1 1 d . . . H20A H 0.5738 1.0126 0.7708 0.048 Uiso 1 1 calc R . . H20B H 0.4653 1.0154 0.7583 0.048 Uiso 1 1 calc R . . C21 C 0.4783(2) 0.94374(12) 0.6558(3) 0.0354(7) Uani 1 1 d . . . H21A H 0.4423 0.9606 0.5525 0.042 Uiso 1 1 calc R . . H21B H 0.5362 0.9207 0.6699 0.042 Uiso 1 1 calc R . . C22 C 0.4017(2) 0.90674(11) 0.6676(3) 0.0311(6) Uani 1 1 d . . . H22A H 0.3781 0.8760 0.5925 0.037 Uiso 1 1 calc R . . H22B H 0.3398 0.9290 0.6414 0.037 Uiso 1 1 calc R . . C23 C 0.8569(2) 0.84493(11) 1.3740(3) 0.0298(6) Uani 1 1 d . . . H23 H 0.9331 0.8403 1.4521 0.036 Uiso 1 1 calc R . . C24 C 0.8045(3) 0.86361(13) 1.4550(4) 0.0452(8) Uani 1 1 d . . . H24A H 0.8204 0.8368 1.5370 0.054 Uiso 1 1 calc R . . H24B H 0.7281 0.8646 1.3811 0.054 Uiso 1 1 calc R . . C25 C 0.8438(3) 0.92174(14) 1.5244(4) 0.0538(9) Uani 1 1 d . . . H25A H 0.9190 0.9198 1.6051 0.065 Uiso 1 1 calc R . . H25B H 0.8070 0.9343 1.5724 0.065 Uiso 1 1 calc R . . C26 C 0.8259(3) 0.96425(14) 1.4020(4) 0.0490(9) Uani 1 1 d . . . H26A H 0.7504 0.9684 1.3249 0.059 Uiso 1 1 calc R . . H26B H 0.8538 1.0010 1.4505 0.059 Uiso 1 1 calc R . . C27 C 0.8800(3) 0.94491(13) 1.3242(4) 0.0430(8) Uani 1 1 d . . . H27A H 0.9562 0.9441 1.4000 0.052 Uiso 1 1 calc R . . H27B H 0.8655 0.9716 1.2427 0.052 Uiso 1 1 calc R . . C28 C 0.8423(2) 0.88659(13) 1.2541(3) 0.0380(7) Uani 1 1 d . . . H28A H 0.7678 0.8884 1.1700 0.046 Uiso 1 1 calc R . . H28B H 0.8819 0.8740 1.2103 0.046 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 0.02409(10) 0.02413(10) 0.02587(10) 0.00086(8) 0.01508(8) 0.00269(8) Pd2 0.02702(10) 0.01923(9) 0.02530(10) -0.00302(8) 0.01465(8) -0.00071(8) Br1 0.03355(16) 0.04016(18) 0.03790(16) 0.00371(13) 0.01880(14) -0.00913(13) Br2 0.04019(18) 0.03143(17) 0.04732(18) 0.00591(14) 0.02912(15) 0.00053(13) N1 0.0354(13) 0.0311(13) 0.0326(13) 0.0038(10) 0.0223(11) 0.0049(11) N2 0.0301(12) 0.0246(13) 0.0313(13) 0.0025(10) 0.0179(11) 0.0029(10) N3 0.0316(13) 0.0325(15) 0.0343(14) -0.0077(11) 0.0167(12) -0.0020(10) N4 0.0369(13) 0.0289(14) 0.0289(13) -0.0013(11) 0.0152(11) -0.0036(11) C1 0.0309(15) 0.0316(16) 0.0291(14) 0.0018(12) 0.0168(12) 0.0034(12) C2 0.0303(14) 0.0226(15) 0.0293(14) 0.0039(11) 0.0183(12) 0.0009(12) C3 0.0303(14) 0.0252(15) 0.0345(15) -0.0020(12) 0.0204(12) -0.0003(12) C4 0.0310(14) 0.0234(15) 0.0259(14) -0.0001(12) 0.0130(12) -0.0013(12) C5 0.0276(14) 0.0355(17) 0.0336(15) 0.0067(12) 0.0184(12) 0.0120(12) C6 0.0311(15) 0.0413(19) 0.0493(19) -0.0009(15) 0.0230(14) 0.0008(13) C7 0.057(2) 0.039(2) 0.064(2) 0.0090(17) 0.0410(19) -0.0033(16) C8 0.065(2) 0.068(3) 0.0420(19) 0.0118(17) 0.0373(19) 0.0137(19) C9 0.0489(19) 0.057(2) 0.0421(18) -0.0111(17) 0.0272(16) 0.0000(16) C10 0.0430(18) 0.0329(17) 0.057(2) -0.0032(15) 0.0343(16) 0.0023(14) C11 0.0254(15) 0.0340(17) 0.0302(15) -0.0103(12) 0.0128(13) -0.0029(12) C12 0.0488(18) 0.0438(19) 0.0255(15) 0.0009(13) 0.0152(14) 0.0039(15) C13 0.064(2) 0.067(3) 0.058(2) -0.0068(19) 0.049(2) -0.0110(19) C14 0.0359(18) 0.067(3) 0.066(2) -0.020(2) 0.0248(18) 0.0027(17) C15 0.0401(18) 0.0316(18) 0.0412(18) -0.0060(14) 0.0047(15) 0.0074(13) C16 0.0503(19) 0.0299(17) 0.0383(17) -0.0059(13) 0.0229(15) -0.0104(14) C17 0.0245(13) 0.0258(15) 0.0371(15) 0.0027(12) 0.0186(12) 0.0032(11) C18 0.0434(17) 0.0358(17) 0.0372(16) -0.0044(13) 0.0267(15) 0.0038(13) C19 0.0373(16) 0.0348(17) 0.0402(17) -0.0067(14) 0.0173(14) -0.0043(13) C20 0.0310(15) 0.0287(17) 0.0553(19) 0.0037(14) 0.0201(15) -0.0003(12) C21 0.0359(15) 0.0352(17) 0.0336(15) 0.0097(13) 0.0182(13) 0.0030(13) C22 0.0271(14) 0.0265(15) 0.0350(15) 0.0002(12) 0.0140(12) 0.0021(11) C23 0.0303(14) 0.0271(15) 0.0257(14) -0.0071(11) 0.0114(12) -0.0088(11) C24 0.068(2) 0.0371(19) 0.0463(19) -0.0119(15) 0.0418(19) -0.0179(16) C25 0.080(3) 0.047(2) 0.060(2) -0.0251(18) 0.055(2) -0.0214(18) C26 0.0406(18) 0.0342(19) 0.062(2) -0.0119(16) 0.0222(17) -0.0050(14) C27 0.053(2) 0.0335(18) 0.0437(18) -0.0002(14) 0.0270(16) -0.0124(15) C28 0.0442(18) 0.0408(18) 0.0319(16) -0.0023(13) 0.0228(15) -0.0102(14) _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 C2 1.957(3) . ? Pd1 C1 1.968(3) . ? Pd1 Pd2 2.5282(3) . ? Pd1 Br1 2.5301(3) . ? Pd2 C4 1.967(3) . ? Pd2 C3 1.967(3) . ? Pd2 Br2 2.5285(4) . ? N1 C1 1.140(3) . ? N1 C5 1.458(3) . ? N2 C2 1.140(3) . ? N2 C17 1.458(3) . ? N3 C3 1.144(3) . ? N3 C11 1.461(3) . ? N4 C4 1.140(3) . ? N4 C23 1.453(3) . ? C5 C6 1.514(4) . ? C5 C10 1.525(4) . ? C6 C7 1.525(4) . ? C7 C8 1.516(5) . ? C8 C9 1.519(5) . ? C9 C10 1.505(4) . ? C11 C16 1.517(4) . ? C11 C12 1.521(4) . ? C12 C13 1.502(5) . ? C13 C14 1.530(5) . ? C14 C15 1.515(5) . ? C15 C16 1.504(4) . ? C17 C18 1.519(4) . ? C17 C22 1.533(4) . ? C18 C19 1.527(4) . ? C19 C20 1.520(4) . ? C20 C21 1.531(4) . ? C21 C22 1.520(4) . ? C23 C28 1.508(4) . ? C23 C24 1.509(4) . ? C24 C25 1.521(4) . ? C25 C26 1.524(5) . ? C26 C27 1.509(5) . ? C27 C28 1.524(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Pd1 C1 174.53(12) . . ? C2 Pd1 Pd2 85.11(8) . . ? C1 Pd1 Pd2 89.47(8) . . ? C2 Pd1 Br1 91.66(8) . . ? C1 Pd1 Br1 93.80(8) . . ? Pd2 Pd1 Br1 174.013(12) . . ? C4 Pd2 C3 169.27(11) . . ? C4 Pd2 Pd1 78.50(8) . . ? C3 Pd2 Pd1 90.78(8) . . ? C4 Pd2 Br2 99.08(8) . . ? C3 Pd2 Br2 91.64(8) . . ? Pd1 Pd2 Br2 177.574(13) . . ? C1 N1 C5 177.8(3) . . ? C2 N2 C17 170.4(3) . . ? C3 N3 C11 169.9(3) . . ? C4 N4 C23 162.3(3) . . ? N1 C1 Pd1 176.0(3) . . ? N2 C2 Pd1 173.7(2) . . ? N3 C3 Pd2 173.2(3) . . ? N4 C4 Pd2 175.8(3) . . ? N1 C5 C6 109.6(2) . . ? N1 C5 C10 108.6(2) . . ? C6 C5 C10 111.9(2) . . ? C5 C6 C7 112.1(2) . . ? C8 C7 C6 110.8(3) . . ? C7 C8 C9 110.6(3) . . ? C10 C9 C8 111.2(3) . . ? C9 C10 C5 112.5(3) . . ? N3 C11 C16 108.3(2) . . ? N3 C11 C12 109.5(3) . . ? C16 C11 C12 112.1(3) . . ? C13 C12 C11 111.6(2) . . ? C12 C13 C14 111.3(3) . . ? C15 C14 C13 111.9(3) . . ? C16 C15 C14 110.6(3) . . ? C15 C16 C11 112.0(3) . . ? N2 C17 C18 108.9(2) . . ? N2 C17 C22 108.7(2) . . ? C18 C17 C22 111.5(2) . . ? C17 C18 C19 112.8(2) . . ? C20 C19 C18 111.5(2) . . ? C19 C20 C21 110.8(2) . . ? C22 C21 C20 111.1(3) . . ? C21 C22 C17 112.1(2) . . ? N4 C23 C28 108.1(2) . . ? N4 C23 C24 110.3(2) . . ? C28 C23 C24 112.5(3) . . ? C23 C24 C25 109.8(3) . . ? C24 C25 C26 111.5(3) . . ? C27 C26 C25 110.1(3) . . ? C26 C27 C28 111.1(3) . . ? C23 C28 C27 111.1(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.286 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.061 # Attachment '4.cif' data_6305a _database_code_depnum_ccdc_archive 'CCDC 703028' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 Br2 N4 Pd' _chemical_formula_weight 720.86 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' Br Br -0.2901 2.4595 '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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 27.983(3) _cell_length_b 16.8551(17) _cell_length_c 13.0760(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6167.3(11) _cell_formula_units_Z 8 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used 3100 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 18.60 _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2896 _exptl_absorpt_coefficient_mu 3.218 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4452 _exptl_absorpt_correction_T_max 0.8821 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 243(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 41611 _diffrn_reflns_av_R_equivalents 0.0868 _diffrn_reflns_av_sigmaI/netI 0.0638 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7085 _reflns_number_gt 4332 _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^)+(0.0669P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7085 _refine_ls_number_parameters 349 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.367051(14) 0.18633(2) 0.52096(3) 0.04383(14) Uani 1 1 d . . . Br1 Br 0.39516(2) 0.08981(4) 0.64599(5) 0.0644(2) Uani 1 1 d . . . Br2 Br 0.33284(2) 0.28534(4) 0.40839(5) 0.0668(2) Uani 1 1 d . . . N1 N 0.26702(17) 0.1570(3) 0.6019(4) 0.0530(12) Uani 1 1 d . . . N2 N 0.28693(16) 0.0689(2) 0.4902(3) 0.0472(11) Uani 1 1 d . . . N3 N 0.45470(17) 0.2585(3) 0.6004(3) 0.0480(11) Uani 1 1 d D . . H3N H 0.442(2) 0.247(4) 0.660(3) 0.080 Uiso 1 1 d D . . N4 N 0.46075(15) 0.2401(2) 0.4309(3) 0.0429(10) Uani 1 1 d D . . H4N H 0.4906(10) 0.252(4) 0.443(5) 0.080 Uiso 1 1 d D . . C1 C 0.30193(18) 0.1356(3) 0.5371(4) 0.0440(12) Uani 1 1 d . . . C2 C 0.2301(2) 0.1020(4) 0.5988(5) 0.0584(15) Uani 1 1 d . . . C3 C 0.1879(2) 0.0964(5) 0.6559(6) 0.082(2) Uani 1 1 d . . . H3 H 0.1791 0.1347 0.7046 0.099 Uiso 1 1 calc R . . C4 C 0.1599(3) 0.0299(5) 0.6352(7) 0.108(3) Uani 1 1 d . . . H4 H 0.1315 0.0227 0.6721 0.129 Uiso 1 1 calc R . . C5 C 0.1722(2) -0.0242(5) 0.5643(7) 0.103(3) Uani 1 1 d . . . H5 H 0.1518 -0.0676 0.5526 0.123 Uiso 1 1 calc R . . C6 C 0.2134(2) -0.0183(4) 0.5088(6) 0.077(2) Uani 1 1 d . . . H6 H 0.2216 -0.0568 0.4599 0.092 Uiso 1 1 calc R . . C7 C 0.24230(19) 0.0456(3) 0.5266(5) 0.0536(14) Uani 1 1 d . . . C8 C 0.2672(3) 0.2309(4) 0.6597(5) 0.089(2) Uani 1 1 d D . . H8 H 0.2948 0.2571 0.6267 0.107 Uiso 1 1 calc R . . C9 C 0.2279(3) 0.2877(4) 0.6261(6) 0.089(2) Uani 1 1 d D . . H9A H 0.1976 0.2702 0.6539 0.133 Uiso 1 1 calc R . . H9B H 0.2261 0.2885 0.5521 0.133 Uiso 1 1 calc R . . H9C H 0.2350 0.3406 0.6510 0.133 Uiso 1 1 calc R . . C10 C 0.2862(4) 0.2256(6) 0.7671(6) 0.172(6) Uani 1 1 d D . . H10A H 0.2597 0.2225 0.8148 0.258 Uiso 1 1 calc R . . H10B H 0.3052 0.2723 0.7820 0.258 Uiso 1 1 calc R . . H10C H 0.3059 0.1786 0.7738 0.258 Uiso 1 1 calc R . . C11 C 0.3154(2) 0.0280(3) 0.4098(4) 0.0562(15) Uani 1 1 d . . . H11 H 0.3445 0.0600 0.3985 0.067 Uiso 1 1 calc R . . C12 C 0.3314(2) -0.0529(4) 0.4463(6) 0.080(2) Uani 1 1 d . . . H12A H 0.3473 -0.0476 0.5119 0.119 Uiso 1 1 calc R . . H12B H 0.3535 -0.0755 0.3970 0.119 Uiso 1 1 calc R . . H12C H 0.3039 -0.0874 0.4534 0.119 Uiso 1 1 calc R . . C13 C 0.2885(3) 0.0261(5) 0.3098(5) 0.094(2) Uani 1 1 d . . . H13A H 0.2595 -0.0050 0.3179 0.141 Uiso 1 1 calc R . . H13B H 0.3084 0.0022 0.2574 0.141 Uiso 1 1 calc R . . H13C H 0.2801 0.0797 0.2898 0.141 Uiso 1 1 calc R . . C14 C 0.43444(18) 0.2331(3) 0.5126(4) 0.0389(12) Uani 1 1 d . . . C15 C 0.5031(2) 0.2889(3) 0.6100(4) 0.0454(13) Uani 1 1 d . . . C16 C 0.5094(2) 0.3705(3) 0.6092(4) 0.0583(15) Uani 1 1 d . . . C17 C 0.5556(3) 0.3996(4) 0.6180(5) 0.0714(19) Uani 1 1 d . . . H17 H 0.5610 0.4546 0.6171 0.086 Uiso 1 1 calc R . . C18 C 0.5940(2) 0.3477(5) 0.6279(5) 0.079(2) Uani 1 1 d . . . H18 H 0.6253 0.3675 0.6333 0.094 Uiso 1 1 calc R . . C19 C 0.5859(2) 0.2671(4) 0.6299(4) 0.0618(16) Uani 1 1 d . . . H19 H 0.6118 0.2322 0.6385 0.074 Uiso 1 1 calc R . . C20 C 0.5405(2) 0.2368(4) 0.6196(4) 0.0513(14) Uani 1 1 d . . . C21 C 0.4674(2) 0.4267(4) 0.6007(5) 0.0705(18) Uani 1 1 d . . . H21A H 0.4790 0.4810 0.5979 0.106 Uiso 1 1 calc R . . H21B H 0.4468 0.4204 0.6598 0.106 Uiso 1 1 calc R . . H21C H 0.4495 0.4149 0.5390 0.106 Uiso 1 1 calc R . . C22 C 0.5332(2) 0.1478(3) 0.6180(5) 0.0634(17) Uani 1 1 d . . . H22A H 0.5025 0.1351 0.6484 0.095 Uiso 1 1 calc R . . H22B H 0.5585 0.1223 0.6568 0.095 Uiso 1 1 calc R . . H22C H 0.5340 0.1290 0.5479 0.095 Uiso 1 1 calc R . . C23 C 0.44446(18) 0.2237(3) 0.3270(4) 0.0429(12) Uani 1 1 d . . . C24 C 0.43849(19) 0.1452(3) 0.2953(4) 0.0479(13) Uani 1 1 d . . . C25 C 0.4217(2) 0.1344(3) 0.1958(5) 0.0561(15) Uani 1 1 d . . . H25 H 0.4164 0.0826 0.1717 0.067 Uiso 1 1 calc R . . C26 C 0.4129(2) 0.1966(4) 0.1329(4) 0.0653(18) Uani 1 1 d . . . H26 H 0.4011 0.1873 0.0667 0.078 Uiso 1 1 calc R . . C27 C 0.4210(2) 0.2731(4) 0.1647(4) 0.0530(14) Uani 1 1 d . . . H27 H 0.4161 0.3155 0.1193 0.064 Uiso 1 1 calc R . . C28 C 0.43638(19) 0.2880(3) 0.2633(4) 0.0450(13) Uani 1 1 d . . . C29 C 0.4518(2) 0.0753(3) 0.3606(5) 0.0614(16) Uani 1 1 d . . . H29A H 0.4858 0.0771 0.3756 0.092 Uiso 1 1 calc R . . H29B H 0.4445 0.0266 0.3243 0.092 Uiso 1 1 calc R . . H29C H 0.4339 0.0770 0.4240 0.092 Uiso 1 1 calc R . . C30 C 0.4421(2) 0.3721(3) 0.3005(5) 0.0604(16) Uani 1 1 d . . . H30A H 0.4406 0.4081 0.2428 0.091 Uiso 1 1 calc R . . H30B H 0.4728 0.3777 0.3344 0.091 Uiso 1 1 calc R . . H30C H 0.4167 0.3845 0.3484 0.091 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 0.0455(2) 0.0364(2) 0.0496(3) 0.00503(19) 0.0025(2) 0.00124(19) Br1 0.0677(4) 0.0559(4) 0.0696(4) 0.0248(3) -0.0066(3) -0.0050(3) Br2 0.0632(4) 0.0673(4) 0.0701(4) 0.0240(3) 0.0067(3) 0.0193(3) N1 0.053(3) 0.047(3) 0.060(3) -0.011(2) 0.003(2) 0.008(2) N2 0.047(3) 0.037(2) 0.057(3) -0.003(2) 0.010(2) 0.002(2) N3 0.051(3) 0.055(3) 0.039(3) 0.007(2) 0.004(2) 0.001(2) N4 0.044(3) 0.039(2) 0.046(3) 0.001(2) -0.002(2) -0.003(2) C1 0.041(3) 0.039(3) 0.053(3) -0.001(3) -0.001(3) 0.008(2) C2 0.048(3) 0.060(4) 0.067(4) -0.004(3) 0.010(3) 0.008(3) C3 0.054(4) 0.089(5) 0.105(6) -0.020(4) 0.024(4) 0.006(4) C4 0.055(5) 0.093(6) 0.175(9) -0.023(6) 0.044(5) -0.007(4) C5 0.051(4) 0.081(5) 0.175(9) -0.031(6) 0.029(5) -0.013(4) C6 0.049(4) 0.064(4) 0.117(6) -0.024(4) 0.010(4) -0.008(3) C7 0.041(3) 0.047(3) 0.073(4) -0.005(3) 0.008(3) 0.004(3) C8 0.130(7) 0.063(4) 0.074(5) -0.019(4) 0.006(5) 0.023(5) C9 0.093(6) 0.054(4) 0.119(6) -0.011(4) 0.007(5) 0.027(4) C10 0.153(9) 0.188(11) 0.175(11) -0.118(9) -0.077(8) 0.080(9) C11 0.057(4) 0.053(3) 0.058(4) -0.009(3) 0.013(3) 0.005(3) C12 0.080(5) 0.064(4) 0.095(5) -0.010(4) 0.013(4) 0.031(4) C13 0.125(7) 0.089(5) 0.067(5) -0.009(4) 0.005(5) 0.030(5) C14 0.047(3) 0.031(3) 0.040(3) 0.005(2) 0.003(2) 0.003(2) C15 0.050(3) 0.052(3) 0.035(3) -0.001(3) -0.007(2) -0.002(3) C16 0.066(4) 0.055(4) 0.053(3) -0.010(3) -0.007(3) 0.004(3) C17 0.077(5) 0.060(4) 0.077(5) -0.010(3) -0.009(4) -0.017(4) C18 0.053(4) 0.093(5) 0.090(5) -0.022(4) -0.013(4) -0.011(4) C19 0.057(4) 0.071(4) 0.057(4) 0.000(3) -0.016(3) 0.011(3) C20 0.057(4) 0.061(4) 0.036(3) -0.001(3) -0.002(3) 0.005(3) C21 0.077(5) 0.057(4) 0.077(4) -0.008(3) -0.008(4) 0.009(3) C22 0.061(4) 0.061(4) 0.068(4) 0.014(3) 0.000(3) 0.014(3) C23 0.044(3) 0.046(3) 0.039(3) -0.005(3) 0.007(2) -0.002(2) C24 0.045(3) 0.042(3) 0.057(3) -0.006(3) 0.015(3) -0.001(3) C25 0.058(4) 0.047(3) 0.063(4) -0.018(3) 0.005(3) -0.011(3) C26 0.065(4) 0.090(5) 0.041(3) -0.014(4) 0.005(3) -0.005(4) C27 0.055(4) 0.061(4) 0.043(3) 0.007(3) 0.004(3) 0.004(3) C28 0.044(3) 0.044(3) 0.047(3) 0.000(3) 0.006(3) -0.004(2) C29 0.064(4) 0.044(3) 0.077(4) -0.003(3) 0.012(3) 0.003(3) C30 0.072(4) 0.040(3) 0.069(4) 0.003(3) 0.007(3) 0.003(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 2.024(5) . ? Pd1 C14 2.047(5) . ? Pd1 Br2 2.4224(7) . ? Pd1 Br1 2.4369(7) . ? N1 C1 1.342(6) . ? N1 C2 1.389(7) . ? N1 C8 1.458(7) . ? N2 C1 1.348(7) . ? N2 C7 1.393(7) . ? N2 C11 1.488(6) . ? N3 C14 1.350(6) . ? N3 C15 1.452(7) . ? N4 C14 1.303(6) . ? N4 C23 1.459(6) . ? C2 C7 1.383(8) . ? C2 C3 1.399(8) . ? C3 C4 1.393(10) . ? C4 C5 1.345(10) . ? C5 C6 1.366(9) . ? C6 C7 1.366(8) . ? C8 C10 1.504(5) . ? C8 C9 1.522(4) . ? C11 C13 1.509(9) . ? C11 C12 1.512(8) . ? C15 C20 1.373(7) . ? C15 C16 1.388(8) . ? C16 C17 1.388(8) . ? C16 C21 1.514(8) . ? C17 C18 1.391(9) . ? C18 C19 1.378(9) . ? C19 C20 1.375(8) . ? C20 C22 1.514(8) . ? C23 C28 1.386(7) . ? C23 C24 1.396(7) . ? C24 C25 1.395(8) . ? C24 C29 1.503(7) . ? C25 C26 1.355(8) . ? C26 C27 1.374(8) . ? C27 C28 1.382(7) . ? C28 C30 1.507(7) . ? 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 C14 176.2(2) . . ? C1 Pd1 Br2 89.92(14) . . ? C14 Pd1 Br2 93.81(13) . . ? C1 Pd1 Br1 86.48(14) . . ? C14 Pd1 Br1 89.74(14) . . ? Br2 Pd1 Br1 174.35(3) . . ? C1 N1 C2 110.1(4) . . ? C1 N1 C8 123.7(5) . . ? C2 N1 C8 126.0(5) . . ? C1 N2 C7 111.0(4) . . ? C1 N2 C11 122.8(4) . . ? C7 N2 C11 126.2(5) . . ? C14 N3 C15 125.2(4) . . ? C14 N4 C23 124.7(4) . . ? N1 C1 N2 106.5(5) . . ? N1 C1 Pd1 127.4(4) . . ? N2 C1 Pd1 125.8(4) . . ? C7 C2 N1 107.1(5) . . ? C7 C2 C3 121.8(6) . . ? N1 C2 C3 131.1(6) . . ? C4 C3 C2 115.1(7) . . ? C5 C4 C3 122.4(7) . . ? C4 C5 C6 122.1(7) . . ? C5 C6 C7 117.8(7) . . ? C6 C7 C2 120.8(6) . . ? C6 C7 N2 134.0(5) . . ? C2 C7 N2 105.1(5) . . ? N1 C8 C10 115.8(6) . . ? N1 C8 C9 112.7(5) . . ? C10 C8 C9 124.2(6) . . ? N2 C11 C13 110.8(5) . . ? N2 C11 C12 110.7(5) . . ? C13 C11 C12 113.8(6) . . ? N4 C14 N3 115.5(5) . . ? N4 C14 Pd1 126.8(4) . . ? N3 C14 Pd1 117.6(4) . . ? C20 C15 C16 122.5(5) . . ? C20 C15 N3 119.6(5) . . ? C16 C15 N3 117.9(5) . . ? C17 C16 C15 118.0(6) . . ? C17 C16 C21 120.6(6) . . ? C15 C16 C21 121.5(6) . . ? C16 C17 C18 120.3(6) . . ? C19 C18 C17 119.6(6) . . ? C20 C19 C18 121.1(6) . . ? C15 C20 C19 118.5(6) . . ? C15 C20 C22 121.9(5) . . ? C19 C20 C22 119.6(6) . . ? C28 C23 C24 122.9(5) . . ? C28 C23 N4 117.5(4) . . ? C24 C23 N4 119.6(5) . . ? C25 C24 C23 116.2(5) . . ? C25 C24 C29 120.8(5) . . ? C23 C24 C29 123.0(5) . . ? C26 C25 C24 121.8(5) . . ? C25 C26 C27 120.8(5) . . ? C26 C27 C28 120.3(6) . . ? C27 C28 C23 118.0(5) . . ? C27 C28 C30 120.4(5) . . ? C23 C28 C30 121.6(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.890 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.110 # Attachment '5.cif' data_6303 _database_code_depnum_ccdc_archive 'CCDC 703029' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H29 N3' _chemical_formula_weight 371.51 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.2291(15) _cell_length_b 13.0532(9) _cell_length_c 17.1124(12) _cell_angle_alpha 90.00 _cell_angle_beta 122.6700(10) _cell_angle_gamma 90.00 _cell_volume 4367.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used 1188 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 20.51 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9829 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 243(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 12607 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3844 _reflns_number_gt 2169 _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^)+(0.0506P)^2^+1.4394P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3844 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1228 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1282 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 N1 N 0.23447(10) 1.02759(18) 0.17449(15) 0.0614(6) Uani 1 1 d . . . N2 N 0.12925(11) 0.96361(19) 0.06368(17) 0.0600(7) Uani 1 1 d . . . H2A H 0.1086(11) 0.9226(18) 0.0243(15) 0.043(8) Uiso 1 1 d . . . N3 N 0.22447(12) 0.88930(17) 0.08021(15) 0.0554(6) Uani 1 1 d . . . H3A H 0.2665(14) 0.888(2) 0.1059(18) 0.077(10) Uiso 1 1 d . . . C1 C 0.19905(11) 0.9631(2) 0.11013(17) 0.0476(6) Uani 1 1 d . . . C2 C 0.30694(12) 1.0262(2) 0.22101(18) 0.0605(7) Uani 1 1 d . . . C3 C 0.33889(14) 1.0952(2) 0.1938(2) 0.0713(8) Uani 1 1 d . . . C4 C 0.40971(16) 1.1018(3) 0.2451(3) 0.0898(10) Uani 1 1 d . . . H4 H 0.4312 1.1485 0.2270 0.108 Uiso 1 1 calc R . . C5 C 0.44870(16) 1.0415(3) 0.3213(3) 0.0929(11) Uani 1 1 d . . . H5 H 0.4966 1.0464 0.3552 0.112 Uiso 1 1 calc R . . C6 C 0.41729(15) 0.9736(3) 0.3481(2) 0.0869(10) Uani 1 1 d . . . H6 H 0.4442 0.9324 0.4007 0.104 Uiso 1 1 calc R . . C7 C 0.34634(14) 0.9650(2) 0.2988(2) 0.0678(8) Uani 1 1 d . . . C8 C 0.29703(16) 1.1651(3) 0.1119(2) 0.1046(12) Uani 1 1 d . . . H8A H 0.3272 1.2108 0.1056 0.157 Uiso 1 1 calc R . . H8B H 0.2661 1.2049 0.1213 0.157 Uiso 1 1 calc R . . H8C H 0.2709 1.1243 0.0559 0.157 Uiso 1 1 calc R . . C9 C 0.31329(16) 0.8921(3) 0.3308(2) 0.0935(10) Uani 1 1 d . . . H9A H 0.2751 0.9258 0.3284 0.140 Uiso 1 1 calc R . . H9B H 0.3465 0.8711 0.3941 0.140 Uiso 1 1 calc R . . H9C H 0.2970 0.8324 0.2908 0.140 Uiso 1 1 calc R . . C10 C 0.09097(11) 1.0328(2) 0.08312(18) 0.0593(7) Uani 1 1 d . . . C11 C 0.07027(13) 1.0010(3) 0.1416(2) 0.0724(9) Uani 1 1 d . . . C12 C 0.02949(16) 1.0665(4) 0.1552(2) 0.0962(13) Uani 1 1 d . . . H12 H 0.0152 1.0467 0.1950 0.115 Uiso 1 1 calc R . . C13 C 0.00978(16) 1.1595(4) 0.1119(3) 0.1067(16) Uani 1 1 d . . . H13 H -0.0183 1.2026 0.1215 0.128 Uiso 1 1 calc R . . C14 C 0.03073(15) 1.1901(3) 0.0545(3) 0.0946(12) Uani 1 1 d . . . H14 H 0.0173 1.2546 0.0256 0.113 Uiso 1 1 calc R . . C15 C 0.07146(13) 1.1272(2) 0.0385(2) 0.0719(9) Uani 1 1 d . . . C16 C 0.09142(17) 0.8991(3) 0.1892(2) 0.0973(11) Uani 1 1 d . . . H16A H 0.0747 0.8922 0.2301 0.146 Uiso 1 1 calc R . . H16B H 0.1409 0.8941 0.2253 0.146 Uiso 1 1 calc R . . H16C H 0.0723 0.8449 0.1432 0.146 Uiso 1 1 calc R . . C17 C 0.09331(16) 1.1603(3) -0.0256(3) 0.1015(11) Uani 1 1 d . . . H17A H 0.0704 1.2237 -0.0560 0.152 Uiso 1 1 calc R . . H17B H 0.0813 1.1077 -0.0721 0.152 Uiso 1 1 calc R . . H17C H 0.1424 1.1708 0.0097 0.152 Uiso 1 1 calc R . . C18 C 0.18549(12) 0.8171(2) 0.00692(18) 0.0531(7) Uani 1 1 d . . . C19 C 0.16530(14) 0.7257(2) 0.0258(2) 0.0660(8) Uani 1 1 d . . . C20 C 0.12966(16) 0.6562(3) -0.0459(3) 0.0903(10) Uani 1 1 d . . . H20 H 0.1153 0.5940 -0.0341 0.108 Uiso 1 1 calc R . . C21 C 0.11489(15) 0.6756(3) -0.1327(3) 0.0954(12) Uani 1 1 d . . . H21 H 0.0909 0.6269 -0.1799 0.114 Uiso 1 1 calc R . . C22 C 0.13490(16) 0.7664(3) -0.1518(2) 0.0857(11) Uani 1 1 d . . . H22 H 0.1247 0.7793 -0.2120 0.103 Uiso 1 1 calc R . . C23 C 0.17039(13) 0.8396(3) -0.0818(2) 0.0660(8) Uani 1 1 d . . . C24 C 0.18175(19) 0.7007(3) 0.1215(2) 0.1017(11) Uani 1 1 d . . . H24A H 0.2306 0.6894 0.1627 0.152 Uiso 1 1 calc R . . H24B H 0.1573 0.6392 0.1191 0.152 Uiso 1 1 calc R . . H24C H 0.1680 0.7572 0.1447 0.152 Uiso 1 1 calc R . . C25 C 0.19109(18) 0.9400(3) -0.1021(2) 0.0968(11) Uani 1 1 d . . . H25A H 0.1644 0.9948 -0.0983 0.145 Uiso 1 1 calc R . . H25B H 0.1829 0.9383 -0.1640 0.145 Uiso 1 1 calc R . . H25C H 0.2393 0.9520 -0.0570 0.145 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 N1 0.0416(12) 0.0668(16) 0.0703(15) -0.0175(13) 0.0266(11) 0.0007(11) N2 0.0426(13) 0.0645(17) 0.0700(16) -0.0238(14) 0.0284(12) -0.0009(11) N3 0.0418(13) 0.0638(16) 0.0590(14) -0.0053(12) 0.0261(11) 0.0097(11) C1 0.0411(14) 0.0519(17) 0.0547(16) 0.0031(13) 0.0290(13) 0.0062(12) C2 0.0442(15) 0.067(2) 0.0635(18) -0.0185(15) 0.0245(14) 0.0026(14) C3 0.0532(18) 0.073(2) 0.087(2) -0.0106(17) 0.0378(17) -0.0027(15) C4 0.057(2) 0.091(3) 0.118(3) -0.011(2) 0.045(2) -0.0059(18) C5 0.0464(18) 0.092(3) 0.117(3) -0.021(2) 0.0288(19) -0.0003(19) C6 0.0572(19) 0.081(3) 0.092(2) -0.0075(19) 0.0207(17) 0.0175(17) C7 0.0565(17) 0.062(2) 0.077(2) -0.0086(17) 0.0305(16) 0.0070(15) C8 0.078(2) 0.109(3) 0.119(3) 0.023(2) 0.048(2) -0.005(2) C9 0.081(2) 0.093(3) 0.093(2) 0.013(2) 0.0381(19) 0.0136(19) C10 0.0348(13) 0.071(2) 0.0677(18) -0.0261(16) 0.0247(13) -0.0031(13) C11 0.0460(16) 0.100(3) 0.070(2) -0.0282(18) 0.0300(15) -0.0035(16) C12 0.056(2) 0.147(4) 0.086(2) -0.043(2) 0.0379(18) -0.002(2) C13 0.0424(19) 0.142(4) 0.108(3) -0.073(3) 0.0225(19) 0.007(2) C14 0.0503(18) 0.078(3) 0.121(3) -0.042(2) 0.0238(19) 0.0082(16) C15 0.0408(15) 0.065(2) 0.094(2) -0.0237(18) 0.0260(15) -0.0012(14) C16 0.089(2) 0.136(4) 0.081(2) -0.011(2) 0.0548(19) -0.009(2) C17 0.078(2) 0.081(3) 0.141(3) 0.016(2) 0.057(2) 0.0083(18) C18 0.0419(14) 0.0584(19) 0.0569(17) -0.0023(14) 0.0254(12) 0.0131(12) C19 0.0644(18) 0.058(2) 0.079(2) -0.0077(17) 0.0410(16) 0.0088(15) C20 0.079(2) 0.071(2) 0.121(3) -0.021(2) 0.054(2) 0.0006(18) C21 0.057(2) 0.101(3) 0.103(3) -0.042(3) 0.027(2) 0.0195(19) C22 0.066(2) 0.115(3) 0.057(2) -0.013(2) 0.0199(16) 0.039(2) C23 0.0527(16) 0.081(2) 0.0621(19) 0.0070(18) 0.0297(14) 0.0286(15) C24 0.137(3) 0.078(3) 0.121(3) 0.013(2) 0.090(3) 0.001(2) C25 0.107(3) 0.112(3) 0.082(2) 0.028(2) 0.058(2) 0.032(2) _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 N1 C1 1.273(3) . ? N1 C2 1.422(3) . ? N2 C1 1.367(3) . ? N2 C10 1.427(3) . ? N3 C1 1.365(3) . ? N3 C18 1.433(3) . ? C2 C7 1.390(4) . ? C2 C3 1.397(4) . ? C3 C4 1.387(4) . ? C3 C8 1.507(4) . ? C4 C5 1.366(5) . ? C5 C6 1.375(4) . ? C6 C7 1.393(4) . ? C7 C9 1.500(4) . ? C10 C11 1.387(4) . ? C10 C15 1.390(4) . ? C11 C12 1.387(4) . ? C11 C16 1.498(4) . ? C12 C13 1.366(5) . ? C13 C14 1.371(5) . ? C14 C15 1.387(4) . ? C15 C17 1.499(4) . ? C18 C19 1.382(4) . ? C18 C23 1.393(3) . ? C19 C20 1.385(4) . ? C19 C24 1.504(4) . ? C20 C21 1.355(4) . ? C21 C22 1.375(5) . ? C22 C23 1.400(4) . ? C23 C25 1.500(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 119.5(2) . . ? C1 N2 C10 124.1(2) . . ? C1 N3 C18 126.5(2) . . ? N1 C1 N3 125.6(2) . . ? N1 C1 N2 120.6(2) . . ? N3 C1 N2 113.8(2) . . ? C7 C2 C3 119.7(3) . . ? C7 C2 N1 120.8(3) . . ? C3 C2 N1 119.1(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 C8 120.0(3) . . ? C2 C3 C8 120.5(3) . . ? C5 C4 C3 121.1(3) . . ? C4 C5 C6 119.5(3) . . ? C5 C6 C7 121.1(3) . . ? C2 C7 C6 119.1(3) . . ? C2 C7 C9 120.8(3) . . ? C6 C7 C9 120.1(3) . . ? C11 C10 C15 121.6(3) . . ? C11 C10 N2 118.8(3) . . ? C15 C10 N2 119.5(3) . . ? C12 C11 C10 118.1(4) . . ? C12 C11 C16 120.6(3) . . ? C10 C11 C16 121.3(3) . . ? C13 C12 C11 121.0(4) . . ? C12 C13 C14 120.2(3) . . ? C13 C14 C15 120.9(4) . . ? C14 C15 C10 118.1(3) . . ? C14 C15 C17 120.7(3) . . ? C10 C15 C17 121.3(3) . . ? C19 C18 C23 121.3(3) . . ? C19 C18 N3 119.8(2) . . ? C23 C18 N3 118.9(3) . . ? C18 C19 C20 118.3(3) . . ? C18 C19 C24 121.6(3) . . ? C20 C19 C24 120.1(3) . . ? C21 C20 C19 121.7(4) . . ? C20 C21 C22 120.3(4) . . ? C21 C22 C23 120.2(3) . . ? C18 C23 C22 118.3(3) . . ? C18 C23 C25 120.8(3) . . ? C22 C23 C25 120.9(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.127 _refine_diff_density_min -0.095 _refine_diff_density_rms 0.027 # Attachment '6.cif' data_7531a _database_code_depnum_ccdc_archive 'CCDC 703030' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H42 Br4 Cl6 N6 Pd2' _chemical_formula_weight 1207.82 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' Br Br -0.2901 2.4595 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 18.1241(9) _cell_length_b 26.0307(12) _cell_length_c 9.1762(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4329.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4196 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.55 _exptl_crystal_description NEEDLE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2344 _exptl_absorpt_coefficient_mu 4.920 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2105 _exptl_absorpt_correction_T_max 0.7567 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 23435 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3814 _reflns_number_gt 3201 _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^)+(0.0619P)^2^+71.7484P] 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 3814 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1614 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.65688(4) 0.32350(2) 0.38702(7) 0.0282(2) Uani 1 1 d . . . Br1 Br 0.61091(6) 0.27961(4) 0.17317(11) 0.0432(3) Uani 1 1 d . . . Br2 Br 0.69683(6) 0.36873(4) 0.60515(12) 0.0467(3) Uani 1 1 d . . . N1 N 0.5732(4) 0.4143(3) 0.2962(8) 0.0296(16) Uani 1 1 d . . . N2 N 0.5117(4) 0.3705(3) 0.4572(8) 0.0292(16) Uani 1 1 d . . . N3 N 0.7542(5) 0.2774(3) 0.3931(9) 0.0372(17) Uani 1 1 d . . . H3A H 0.7824 0.2861 0.3148 0.045 Uiso 1 1 calc R . . H3B H 0.7800 0.2863 0.4743 0.045 Uiso 1 1 calc R . . C1 C 0.5743(4) 0.3719(3) 0.3787(9) 0.0239(17) Uani 1 1 d . . . C2 C 0.5089(5) 0.4417(3) 0.3230(10) 0.034(2) Uani 1 1 d . . . C3 C 0.4820(6) 0.4885(4) 0.2704(12) 0.051(3) Uani 1 1 d . . . H3 H 0.5090 0.5082 0.2029 0.061 Uiso 1 1 calc R . . C4 C 0.4148(7) 0.5046(5) 0.3211(13) 0.064(4) Uani 1 1 d . . . H4 H 0.3956 0.5360 0.2870 0.076 Uiso 1 1 calc R . . C5 C 0.3740(7) 0.4765(5) 0.4205(13) 0.061(3) Uani 1 1 d . . . H5 H 0.3280 0.4889 0.4520 0.073 Uiso 1 1 calc R . . C6 C 0.4002(5) 0.4303(5) 0.4742(12) 0.050(3) Uani 1 1 d . . . H6 H 0.3727 0.4108 0.5412 0.060 Uiso 1 1 calc R . . C7 C 0.4696(5) 0.4137(3) 0.4246(10) 0.033(2) Uani 1 1 d . . . C8 C 0.6312(6) 0.4266(4) 0.1867(12) 0.044(2) Uani 1 1 d . . . H8 H 0.6660 0.3973 0.1872 0.053 Uiso 1 1 calc R . . C9 C 0.6748(8) 0.4728(5) 0.2352(18) 0.079(5) Uani 1 1 d . . . H9A H 0.7119 0.4809 0.1625 0.119 Uiso 1 1 calc R . . H9B H 0.6987 0.4654 0.3274 0.119 Uiso 1 1 calc R . . H9C H 0.6419 0.5019 0.2470 0.119 Uiso 1 1 calc R . . C10 C 0.6016(8) 0.4301(6) 0.0364(12) 0.070(4) Uani 1 1 d . . . H10A H 0.5682 0.4016 0.0190 0.105 Uiso 1 1 calc R . . H10B H 0.6421 0.4285 -0.0327 0.105 Uiso 1 1 calc R . . H10C H 0.5754 0.4623 0.0245 0.105 Uiso 1 1 calc R . . C11 C 0.4941(5) 0.3289(4) 0.5590(12) 0.043(2) Uani 1 1 d . . . H11 H 0.5364 0.3049 0.5588 0.052 Uiso 1 1 calc R . . C12 C 0.4854(8) 0.3486(6) 0.7134(14) 0.073(4) Uani 1 1 d . . . H12A H 0.5295 0.3671 0.7417 0.109 Uiso 1 1 calc R . . H12B H 0.4778 0.3199 0.7789 0.109 Uiso 1 1 calc R . . H12C H 0.4431 0.3715 0.7183 0.109 Uiso 1 1 calc R . . C13 C 0.4269(7) 0.2992(5) 0.5039(18) 0.076(4) Uani 1 1 d . . . H13A H 0.3832 0.3205 0.5123 0.113 Uiso 1 1 calc R . . H13B H 0.4206 0.2683 0.5617 0.113 Uiso 1 1 calc R . . H13C H 0.4344 0.2898 0.4026 0.113 Uiso 1 1 calc R . . C1S C 0.3383(11) 0.3738(8) 0.135(2) 0.120(8) Uani 1 1 d . . . H1S H 0.3408 0.3939 0.2261 0.144 Uiso 1 1 calc R . . Cl1 Cl 0.4243(3) 0.34495(19) 0.1050(5) 0.0998(14) Uani 1 1 d . . . Cl2 Cl 0.2740(4) 0.3281(5) 0.1539(13) 0.247(6) Uani 1 1 d . . . Cl3 Cl 0.3187(5) 0.4147(3) -0.0048(13) 0.233(5) 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 Pd1 0.0276(4) 0.0272(4) 0.0299(4) 0.0019(3) 0.0022(3) 0.0117(3) Br1 0.0473(6) 0.0404(5) 0.0418(6) -0.0128(4) 0.0011(5) -0.0015(4) Br2 0.0388(5) 0.0540(6) 0.0474(6) -0.0097(5) -0.0142(5) 0.0083(5) N1 0.030(4) 0.026(4) 0.032(4) 0.004(3) 0.002(3) 0.007(3) N2 0.027(4) 0.031(4) 0.030(4) 0.001(3) -0.002(3) 0.007(3) N3 0.039(4) 0.035(4) 0.038(4) 0.001(3) -0.004(4) 0.001(4) C1 0.027(4) 0.022(4) 0.023(4) -0.001(3) 0.000(3) 0.007(3) C2 0.038(5) 0.031(5) 0.032(5) -0.003(4) -0.006(4) 0.014(4) C3 0.062(7) 0.045(6) 0.047(6) 0.011(5) -0.004(5) 0.023(5) C4 0.085(9) 0.055(7) 0.051(7) 0.003(6) -0.009(7) 0.054(7) C5 0.051(7) 0.084(9) 0.048(7) -0.008(6) -0.006(6) 0.046(7) C6 0.030(5) 0.073(8) 0.048(6) -0.001(6) 0.000(5) 0.017(5) C7 0.031(5) 0.037(5) 0.030(5) -0.007(4) -0.005(4) 0.016(4) C8 0.045(6) 0.039(5) 0.049(6) 0.008(5) 0.017(5) 0.009(5) C9 0.079(9) 0.054(8) 0.105(12) -0.005(8) 0.043(9) -0.022(7) C10 0.087(9) 0.090(10) 0.033(6) 0.016(6) 0.005(6) 0.034(8) C11 0.031(5) 0.044(6) 0.054(6) 0.016(5) 0.010(5) 0.005(4) C12 0.078(9) 0.091(10) 0.050(8) 0.024(7) 0.018(7) 0.017(8) C13 0.067(8) 0.049(7) 0.111(12) 0.017(8) 0.015(8) -0.018(6) C1S 0.118(15) 0.101(13) 0.140(18) -0.034(12) -0.067(14) 0.033(12) Cl1 0.092(3) 0.103(3) 0.105(3) -0.026(3) -0.001(3) 0.003(2) Cl2 0.095(5) 0.332(12) 0.314(13) 0.120(10) -0.033(6) -0.053(6) Cl3 0.228(9) 0.152(6) 0.319(13) 0.085(8) -0.087(9) 0.034(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 C1 1.958(8) . ? Pd1 N3 2.133(8) . ? Pd1 Br1 2.4187(12) . ? Pd1 Br2 2.4324(12) . ? N1 C1 1.340(10) . ? N1 C2 1.389(11) . ? N1 C8 1.488(12) . ? N2 C1 1.344(11) . ? N2 C7 1.391(11) . ? N2 C11 1.465(12) . ? N3 N3 1.437(14) 2_655 ? C2 C7 1.381(14) . ? C2 C3 1.398(13) . ? C3 C4 1.371(16) . ? C4 C5 1.384(18) . ? C5 C6 1.384(16) . ? C6 C7 1.406(13) . ? C8 C10 1.483(16) . ? C8 C9 1.505(16) . ? C11 C12 1.514(17) . ? C11 C13 1.529(16) . ? C1S Cl2 1.67(2) . ? C1S Cl3 1.70(2) . ? C1S Cl1 1.75(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 C1 Pd1 N3 174.1(3) . . ? C1 Pd1 Br1 90.5(2) . . ? N3 Pd1 Br1 92.3(2) . . ? C1 Pd1 Br2 87.0(2) . . ? N3 Pd1 Br2 90.3(2) . . ? Br1 Pd1 Br2 177.16(4) . . ? C1 N1 C2 109.5(7) . . ? C1 N1 C8 123.3(7) . . ? C2 N1 C8 127.0(7) . . ? C1 N2 C7 109.0(7) . . ? C1 N2 C11 123.1(7) . . ? C7 N2 C11 128.0(7) . . ? N3 N3 Pd1 118.2(8) 2_655 . ? N1 C1 N2 108.2(7) . . ? N1 C1 Pd1 124.3(6) . . ? N2 C1 Pd1 127.4(6) . . ? C7 C2 N1 106.4(7) . . ? C7 C2 C3 121.0(9) . . ? N1 C2 C3 132.7(9) . . ? C4 C3 C2 117.3(11) . . ? C3 C4 C5 122.5(10) . . ? C4 C5 C6 120.8(10) . . ? C5 C6 C7 117.3(11) . . ? C2 C7 N2 106.9(7) . . ? C2 C7 C6 121.2(9) . . ? N2 C7 C6 132.0(9) . . ? C10 C8 N1 112.7(9) . . ? C10 C8 C9 114.6(11) . . ? N1 C8 C9 110.1(9) . . ? N2 C11 C12 111.7(9) . . ? N2 C11 C13 109.7(9) . . ? C12 C11 C13 113.5(10) . . ? Cl2 C1S Cl3 112.3(11) . . ? Cl2 C1S Cl1 109.3(11) . . ? Cl3 C1S Cl1 109.7(14) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 3.755 _refine_diff_density_min -1.328 _refine_diff_density_rms 0.175 # Attachment '7.cif' data_7442 _database_code_depnum_ccdc_archive 'CCDC 703031' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H29 Cl2 F6 N3 O4 Pd' _chemical_formula_weight 750.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 8.5994(10) _cell_length_b 10.3393(12) _cell_length_c 19.243(2) _cell_angle_alpha 88.083(2) _cell_angle_beta 85.830(2) _cell_angle_gamma 73.500(2) _cell_volume 1635.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8434 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 24.84 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6454 _exptl_absorpt_correction_T_max 0.7727 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 21260 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7488 _reflns_number_gt 6718 _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^)+(0.0621P)^2^+0.3067P] 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 7488 _refine_ls_number_parameters 431 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _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 0.66094(2) 0.706453(17) 0.748209(8) 0.05013(8) Uani 1 1 d . . . O1 O 0.7390(3) 0.8344(2) 0.80708(10) 0.0691(5) Uani 1 1 d . A . O2 O 0.8920(3) 0.6863(3) 0.87905(16) 0.1002(8) Uani 1 1 d . A . O3 O 0.6799(2) 0.83761(18) 0.66848(9) 0.0621(4) Uani 1 1 d . . . O4 O 0.8704(3) 0.6865(2) 0.60531(13) 0.0814(6) Uani 1 1 d . . . F1A F 0.897(3) 0.9964(16) 0.8460(6) 0.146(7) Uani 0.333(14) 1 d PD A 2 F3A F 0.951(3) 0.8993(14) 0.9406(10) 0.189(11) Uani 0.333(14) 1 d PD A 2 F2A F 0.7092(15) 0.9924(19) 0.9210(12) 0.156(8) Uani 0.333(14) 1 d PD A 2 F1 F 0.8084(14) 1.0339(6) 0.8661(5) 0.144(4) Uani 0.667(14) 1 d PD A 1 F2 F 0.8226(14) 0.9174(8) 0.9576(3) 0.134(4) Uani 0.667(14) 1 d PD A 1 F3 F 1.0271(6) 0.8939(8) 0.8889(5) 0.148(3) Uani 0.667(14) 1 d PD A 1 F4 F 0.8481(3) 1.0014(2) 0.59329(13) 0.1032(7) Uani 1 1 d . . . F5 F 0.6449(3) 0.9793(2) 0.54570(13) 0.1105(8) Uani 1 1 d . . . F6 F 0.8817(4) 0.8690(3) 0.50995(13) 0.1448(12) Uani 1 1 d . . . N1 N 0.6457(2) 0.4744(2) 0.66338(10) 0.0503(4) Uani 1 1 d . . . N2 N 0.4263(2) 0.6429(2) 0.66108(10) 0.0524(4) Uani 1 1 d . . . N3 N 0.6036(3) 0.5120(2) 0.86352(11) 0.0602(5) Uani 1 1 d . . . C1 C 0.5737(3) 0.5990(2) 0.68733(12) 0.0489(5) Uani 1 1 d . . . C2 C 0.5432(3) 0.4374(3) 0.61981(12) 0.0517(5) Uani 1 1 d . . . C3 C 0.5612(4) 0.3201(3) 0.58237(15) 0.0657(7) Uani 1 1 d . . . H3 H 0.6550 0.2480 0.5831 0.079 Uiso 1 1 calc R . . C4 C 0.4333(4) 0.3168(3) 0.54453(16) 0.0752(8) Uani 1 1 d . . . H4 H 0.4404 0.2398 0.5194 0.090 Uiso 1 1 calc R . . C5 C 0.2943(4) 0.4238(4) 0.54242(15) 0.0737(8) Uani 1 1 d . . . H5 H 0.2118 0.4174 0.5152 0.088 Uiso 1 1 calc R . . C6 C 0.2747(3) 0.5392(3) 0.57932(14) 0.0646(7) Uani 1 1 d . . . H6 H 0.1803 0.6105 0.5781 0.077 Uiso 1 1 calc R . . C7 C 0.4029(3) 0.5451(3) 0.61888(12) 0.0528(5) Uani 1 1 d . . . C8 C 0.8094(3) 0.3921(3) 0.68232(15) 0.0596(6) Uani 1 1 d . . . H8 H 0.8532 0.4482 0.7111 0.071 Uiso 1 1 calc R . . C9 C 0.9242(3) 0.3543(3) 0.61757(18) 0.0767(8) Uani 1 1 d . . . H9A H 0.8909 0.2914 0.5907 0.115 Uiso 1 1 calc R . . H9B H 1.0328 0.3138 0.6312 0.115 Uiso 1 1 calc R . . H9C H 0.9214 0.4339 0.5899 0.115 Uiso 1 1 calc R . . C10 C 0.7953(4) 0.2695(3) 0.72670(18) 0.0794(8) Uani 1 1 d . . . H10A H 0.7204 0.2991 0.7663 0.119 Uiso 1 1 calc R . . H10B H 0.9001 0.2219 0.7423 0.119 Uiso 1 1 calc R . . H10C H 0.7567 0.2106 0.6993 0.119 Uiso 1 1 calc R . . C11 C 0.3087(3) 0.7758(3) 0.67754(15) 0.0653(7) Uani 1 1 d . . . H11 H 0.3602 0.8206 0.7094 0.078 Uiso 1 1 calc R . . C12 C 0.1562(4) 0.7565(4) 0.71684(17) 0.0870(10) Uani 1 1 d . . . H12A H 0.1059 0.7074 0.6884 0.131 Uiso 1 1 calc R . . H12B H 0.0816 0.8430 0.7275 0.131 Uiso 1 1 calc R . . H12C H 0.1852 0.7069 0.7593 0.131 Uiso 1 1 calc R . . C13 C 0.2769(4) 0.8644(4) 0.61327(19) 0.0865(10) Uani 1 1 d . . . H13A H 0.3774 0.8767 0.5933 0.130 Uiso 1 1 calc R . . H13B H 0.2033 0.9505 0.6257 0.130 Uiso 1 1 calc R . . H13C H 0.2297 0.8224 0.5799 0.130 Uiso 1 1 calc R . . C14 C 0.6276(3) 0.5877(3) 0.82241(13) 0.0572(6) Uani 1 1 d . . . C15 C 0.5721(3) 0.4188(3) 0.91318(13) 0.0588(6) Uani 1 1 d . . . C16 C 0.7005(4) 0.3447(3) 0.95145(15) 0.0675(7) Uani 1 1 d . . . C17 C 0.6630(4) 0.2531(3) 0.99972(17) 0.0808(9) Uani 1 1 d . . . H17 H 0.7445 0.2000 1.0261 0.097 Uiso 1 1 calc R . . C18 C 0.5104(5) 0.2391(3) 1.00934(18) 0.0850(9) Uani 1 1 d . . . H18 H 0.4886 0.1788 1.0430 0.102 Uiso 1 1 calc R . . C19 C 0.3894(5) 0.3121(4) 0.97043(19) 0.0857(9) Uani 1 1 d . . . H19 H 0.2864 0.2997 0.9772 0.103 Uiso 1 1 calc R . . C20 C 0.4166(4) 0.4052(3) 0.92068(16) 0.0691(7) Uani 1 1 d . . . C21 C 0.8673(4) 0.3619(4) 0.9403(2) 0.0971(11) Uani 1 1 d . . . H21A H 0.9272 0.3031 0.9040 0.146 Uiso 1 1 calc R . . H21B H 0.9223 0.3399 0.9826 0.146 Uiso 1 1 calc R . . H21C H 0.8596 0.4538 0.9271 0.146 Uiso 1 1 calc R . . C22 C 0.2837(5) 0.4886(5) 0.8777(2) 0.1031(12) Uani 1 1 d . . . H22A H 0.1805 0.4810 0.8970 0.155 Uiso 1 1 calc R . . H22B H 0.3016 0.4566 0.8307 0.155 Uiso 1 1 calc R . . H22C H 0.2841 0.5813 0.8779 0.155 Uiso 1 1 calc R . . C23 C 0.8317(3) 0.7966(3) 0.85644(14) 0.0609(6) Uani 1 1 d . . . C24 C 0.8692(9) 0.9122(9) 0.8920(3) 0.084(4) Uani 0.667(14) 1 d PD A 1 C24A C 0.8482(15) 0.9231(12) 0.8933(5) 0.091(9) Uani 0.333(14) 1 d PD A 2 C25 C 0.7813(3) 0.7975(2) 0.61792(13) 0.0516(5) Uani 1 1 d . . . C26 C 0.7882(4) 0.9121(3) 0.56592(15) 0.0667(7) Uani 1 1 d . . . C1S C 0.4311(6) 0.1020(5) 0.7896(3) 0.1236(16) Uani 1 1 d . . . H1S1 H 0.4791 0.1463 0.8223 0.148 Uiso 1 1 calc R . . H1S2 H 0.5184 0.0332 0.7662 0.148 Uiso 1 1 calc R . . Cl1 Cl 0.3035(3) 0.0263(2) 0.83468(11) 0.1834(8) Uani 1 1 d . . . Cl2 Cl 0.3407(3) 0.2165(3) 0.72981(11) 0.1937(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 Pd1 0.05502(12) 0.04982(12) 0.04397(11) 0.00135(7) -0.00265(7) -0.01262(8) O1 0.0869(13) 0.0596(11) 0.0626(11) 0.0000(9) -0.0189(10) -0.0204(10) O2 0.1048(19) 0.0745(15) 0.125(2) 0.0202(15) -0.0483(16) -0.0234(13) O3 0.0757(12) 0.0507(9) 0.0553(10) 0.0049(8) 0.0002(8) -0.0122(8) O4 0.0804(14) 0.0549(11) 0.0956(16) 0.0074(10) 0.0160(11) -0.0040(10) F1A 0.248(18) 0.092(9) 0.134(9) -0.010(7) 0.018(10) -0.114(11) F3A 0.27(2) 0.162(10) 0.170(18) 0.033(12) -0.181(19) -0.084(16) F2A 0.130(8) 0.145(12) 0.193(16) -0.116(12) 0.014(9) -0.033(8) F1 0.254(11) 0.072(3) 0.121(5) 0.007(3) -0.091(6) -0.055(4) F2 0.213(9) 0.142(5) 0.072(3) -0.030(3) 0.016(4) -0.091(6) F3 0.118(3) 0.199(6) 0.164(6) -0.030(6) -0.024(4) -0.099(4) F4 0.1199(17) 0.0748(12) 0.1322(18) 0.0192(12) -0.0275(14) -0.0533(12) F5 0.1085(16) 0.1070(16) 0.1209(17) 0.0628(14) -0.0490(14) -0.0354(13) F6 0.216(3) 0.0995(17) 0.0936(16) 0.0133(13) 0.0701(18) -0.0252(18) N1 0.0459(10) 0.0482(10) 0.0552(11) 0.0000(8) -0.0020(8) -0.0111(8) N2 0.0465(10) 0.0565(11) 0.0486(10) -0.0007(8) -0.0022(8) -0.0056(8) N3 0.0680(13) 0.0645(13) 0.0473(11) 0.0007(10) 0.0010(9) -0.0187(11) C1 0.0500(12) 0.0514(12) 0.0425(11) 0.0032(9) 0.0002(9) -0.0111(10) C2 0.0498(12) 0.0565(13) 0.0502(12) 0.0013(10) 0.0013(10) -0.0186(10) C3 0.0678(16) 0.0612(15) 0.0695(16) -0.0077(13) 0.0016(13) -0.0213(13) C4 0.087(2) 0.079(2) 0.0683(17) -0.0152(15) 0.0016(15) -0.0377(17) C5 0.0712(18) 0.105(2) 0.0562(15) -0.0036(15) -0.0067(13) -0.0417(18) C6 0.0546(14) 0.0850(19) 0.0537(14) 0.0016(13) -0.0057(11) -0.0187(13) C7 0.0495(12) 0.0608(14) 0.0470(12) 0.0018(10) 0.0024(9) -0.0154(11) C8 0.0495(13) 0.0530(13) 0.0723(16) -0.0001(12) -0.0101(11) -0.0066(10) C9 0.0535(15) 0.0740(19) 0.092(2) -0.0008(16) 0.0085(14) -0.0044(13) C10 0.084(2) 0.0640(17) 0.081(2) 0.0128(15) -0.0127(16) -0.0050(15) C11 0.0532(14) 0.0663(16) 0.0641(15) -0.0067(12) -0.0030(11) 0.0032(12) C12 0.0623(17) 0.109(3) 0.0717(19) -0.0097(18) 0.0138(14) 0.0010(17) C13 0.082(2) 0.074(2) 0.086(2) 0.0116(17) -0.0058(17) 0.0049(16) C14 0.0604(14) 0.0633(15) 0.0473(12) -0.0016(11) -0.0031(10) -0.0167(12) C15 0.0719(16) 0.0565(14) 0.0466(12) -0.0015(10) 0.0056(11) -0.0183(12) C16 0.0690(17) 0.0658(17) 0.0633(16) 0.0046(13) 0.0011(13) -0.0139(13) C17 0.093(2) 0.0683(18) 0.0729(19) 0.0163(15) -0.0051(16) -0.0124(16) C18 0.103(3) 0.073(2) 0.078(2) 0.0145(16) 0.0143(18) -0.0305(19) C19 0.084(2) 0.092(2) 0.087(2) 0.0051(18) 0.0127(18) -0.0400(19) C20 0.0719(17) 0.0724(18) 0.0651(16) -0.0004(13) 0.0000(13) -0.0246(14) C21 0.068(2) 0.108(3) 0.110(3) 0.030(2) -0.0074(18) -0.0200(19) C22 0.082(2) 0.126(3) 0.108(3) 0.022(2) -0.026(2) -0.037(2) C23 0.0560(14) 0.0682(17) 0.0604(15) 0.0027(12) -0.0026(11) -0.0214(12) C24 0.076(4) 0.109(7) 0.070(6) 0.017(4) -0.003(4) -0.032(4) C24A 0.139(17) 0.054(8) 0.098(16) -0.007(8) -0.072(12) -0.043(9) C25 0.0533(13) 0.0496(13) 0.0537(13) 0.0029(10) -0.0101(10) -0.0161(10) C26 0.0764(18) 0.0580(15) 0.0662(16) 0.0068(12) -0.0027(14) -0.0213(13) C1S 0.093(3) 0.093(3) 0.180(5) 0.015(3) -0.011(3) -0.022(2) Cl1 0.1938(17) 0.1839(17) 0.1911(18) 0.0269(14) 0.0286(14) -0.0970(15) Cl2 0.1765(17) 0.233(2) 0.1672(15) 0.0846(16) -0.0346(13) -0.0552(15) _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 C14 1.911(3) . ? Pd1 C1 1.964(2) . ? Pd1 O3 2.0419(18) . ? Pd1 O1 2.0494(19) . ? O1 C23 1.264(3) . ? O2 C23 1.193(4) . ? O3 C25 1.256(3) . ? O4 C25 1.206(3) . ? F1A C24A 1.287(9) . ? F3A C24A 1.285(8) . ? F2A C24A 1.294(9) . ? F1 C24 1.315(7) . ? F2 C24 1.293(6) . ? F3 C24 1.314(7) . ? F4 C26 1.317(3) . ? F5 C26 1.311(4) . ? F6 C26 1.307(4) . ? N1 C1 1.341(3) . ? N1 C2 1.395(3) . ? N1 C8 1.487(3) . ? N2 C1 1.349(3) . ? N2 C7 1.384(3) . ? N2 C11 1.485(3) . ? N3 C14 1.144(3) . ? N3 C15 1.401(3) . ? C2 C7 1.391(3) . ? C2 C3 1.397(4) . ? C3 C4 1.371(4) . ? C4 C5 1.381(5) . ? C5 C6 1.372(4) . ? C6 C7 1.401(4) . ? C8 C9 1.522(4) . ? C8 C10 1.534(4) . ? C11 C13 1.508(4) . ? C11 C12 1.525(4) . ? C15 C20 1.380(4) . ? C15 C16 1.396(4) . ? C16 C17 1.391(4) . ? C16 C21 1.494(4) . ? C17 C18 1.359(5) . ? C18 C19 1.357(5) . ? C19 C20 1.390(5) . ? C20 C22 1.505(5) . ? C23 C24 1.520(9) . ? C23 C24A 1.555(11) . ? C25 C26 1.537(4) . ? C1S Cl2 1.687(5) . ? C1S Cl1 1.695(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 C14 Pd1 C1 86.94(10) . . ? C14 Pd1 O3 176.11(9) . . ? C1 Pd1 O3 91.41(9) . . ? C14 Pd1 O1 97.02(10) . . ? C1 Pd1 O1 174.59(8) . . ? O3 Pd1 O1 84.41(8) . . ? C23 O1 Pd1 124.20(19) . . ? C25 O3 Pd1 119.35(16) . . ? C1 N1 C2 109.4(2) . . ? C1 N1 C8 123.5(2) . . ? C2 N1 C8 127.1(2) . . ? C1 N2 C7 109.8(2) . . ? C1 N2 C11 123.6(2) . . ? C7 N2 C11 126.6(2) . . ? C14 N3 C15 179.0(3) . . ? N1 C1 N2 108.0(2) . . ? N1 C1 Pd1 128.11(18) . . ? N2 C1 Pd1 123.92(18) . . ? C7 C2 N1 106.4(2) . . ? C7 C2 C3 121.8(2) . . ? N1 C2 C3 131.8(2) . . ? C4 C3 C2 116.4(3) . . ? C3 C4 C5 122.3(3) . . ? C6 C5 C4 121.8(3) . . ? C5 C6 C7 117.2(3) . . ? N2 C7 C2 106.4(2) . . ? N2 C7 C6 133.1(2) . . ? C2 C7 C6 120.5(2) . . ? N1 C8 C9 110.8(2) . . ? N1 C8 C10 110.2(2) . . ? C9 C8 C10 113.1(2) . . ? N2 C11 C13 111.3(2) . . ? N2 C11 C12 110.2(3) . . ? C13 C11 C12 114.4(3) . . ? N3 C14 Pd1 175.2(2) . . ? C20 C15 C16 124.2(3) . . ? C20 C15 N3 118.0(3) . . ? C16 C15 N3 117.8(3) . . ? C17 C16 C15 115.5(3) . . ? C17 C16 C21 122.5(3) . . ? C15 C16 C21 121.9(3) . . ? C18 C17 C16 121.7(3) . . ? C19 C18 C17 120.8(3) . . ? C18 C19 C20 121.2(3) . . ? C15 C20 C19 116.5(3) . . ? C15 C20 C22 121.4(3) . . ? C19 C20 C22 122.1(3) . . ? O2 C23 O1 130.4(3) . . ? O2 C23 C24 116.2(4) . . ? O1 C23 C24 113.5(4) . . ? O2 C23 C24A 120.4(5) . . ? O1 C23 C24A 109.0(5) . . ? C24 C23 C24A 6.7(6) . . ? F2 C24 F3 106.1(7) . . ? F2 C24 F1 106.6(7) . . ? F3 C24 F1 105.1(7) . . ? F2 C24 C23 111.8(6) . . ? F3 C24 C23 109.7(6) . . ? F1 C24 C23 116.8(6) . . ? F3A C24A F1A 107.0(10) . . ? F3A C24A F2A 108.1(10) . . ? F1A C24A F2A 108.4(10) . . ? F3A C24A C23 115.5(10) . . ? F1A C24A C23 106.8(9) . . ? F2A C24A C23 110.8(8) . . ? O4 C25 O3 130.2(2) . . ? O4 C25 C26 117.7(2) . . ? O3 C25 C26 112.1(2) . . ? F6 C26 F5 107.4(3) . . ? F6 C26 F4 105.9(3) . . ? F5 C26 F4 106.2(3) . . ? F6 C26 C25 112.5(2) . . ? F5 C26 C25 112.9(2) . . ? F4 C26 C25 111.5(2) . . ? Cl2 C1S Cl1 114.0(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.431 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.076 # Attachment 'cis-2a.cif' data_5401a _database_code_depnum_ccdc_archive 'CCDC 703032' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 Br2 N3 Pd' _chemical_formula_weight 577.68 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' Br Br -0.2901 2.4595 '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 10.1903(7) _cell_length_b 13.3919(9) _cell_length_c 17.0572(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2327.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6327 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 21.95 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 4.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3628 _exptl_absorpt_correction_T_max 0.6302 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 30682 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5350 _reflns_number_gt 4880 _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^)+(0.0339P)^2^+0.4089P] 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 0.031(7) _refine_ls_number_reflns 5350 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.68253(3) 0.723709(19) 0.384740(16) 0.02892(7) Uani 1 1 d . . . Br1 Br 0.79658(5) 0.83110(3) 0.29189(3) 0.05861(15) Uani 1 1 d . . . Br2 Br 0.65282(5) 0.85313(3) 0.48517(3) 0.05037(13) Uani 1 1 d . . . N1 N 0.7992(3) 0.5461(2) 0.30786(18) 0.0317(7) Uani 1 1 d . . . N2 N 0.6152(3) 0.5891(2) 0.25311(18) 0.0335(7) Uani 1 1 d . . . N3 N 0.5308(4) 0.5717(2) 0.4836(2) 0.0412(8) Uani 1 1 d . . . C1 C 0.7007(4) 0.6132(3) 0.3084(2) 0.0293(8) Uani 1 1 d . . . C2 C 0.7757(4) 0.4758(3) 0.2489(2) 0.0348(9) Uani 1 1 d . . . C3 C 0.8463(4) 0.3935(3) 0.2237(3) 0.0448(10) Uani 1 1 d . . . H3 H 0.9257 0.3751 0.2477 0.054 Uiso 1 1 calc R . . C4 C 0.7956(5) 0.3395(3) 0.1620(3) 0.0527(12) Uani 1 1 d . . . H4 H 0.8415 0.2836 0.1430 0.063 Uiso 1 1 calc R . . C5 C 0.6757(5) 0.3670(4) 0.1271(3) 0.0561(12) Uani 1 1 d . . . H5 H 0.6426 0.3283 0.0855 0.067 Uiso 1 1 calc R . . C6 C 0.6068(5) 0.4477(3) 0.1518(3) 0.0476(11) Uani 1 1 d . . . H6 H 0.5272 0.4657 0.1278 0.057 Uiso 1 1 calc R . . C7 C 0.6576(4) 0.5031(3) 0.2136(2) 0.0365(9) Uani 1 1 d . . . C8 C 0.9148(4) 0.5524(3) 0.3611(2) 0.0317(8) Uani 1 1 d . . . H8 H 0.9015 0.6114 0.3952 0.038 Uiso 1 1 calc R . . C9 C 1.0377(4) 0.5701(4) 0.3152(2) 0.0463(11) Uani 1 1 d . . . H9A H 1.0515 0.5151 0.2791 0.069 Uiso 1 1 calc R . . H9B H 1.1117 0.5747 0.3508 0.069 Uiso 1 1 calc R . . H9C H 1.0297 0.6319 0.2859 0.069 Uiso 1 1 calc R . . C10 C 0.9198(5) 0.4613(3) 0.4140(3) 0.0535(12) Uani 1 1 d . . . H10A H 0.8412 0.4589 0.4461 0.080 Uiso 1 1 calc R . . H10B H 0.9964 0.4655 0.4477 0.080 Uiso 1 1 calc R . . H10C H 0.9251 0.4015 0.3822 0.080 Uiso 1 1 calc R . . C11 C 0.4978(4) 0.6505(3) 0.2347(3) 0.0410(10) Uani 1 1 d . . . H11 H 0.4964 0.7062 0.2730 0.049 Uiso 1 1 calc R . . C12 C 0.3722(5) 0.5932(4) 0.2459(3) 0.0590(13) Uani 1 1 d . . . H12A H 0.3676 0.5397 0.2076 0.089 Uiso 1 1 calc R . . H12B H 0.2981 0.6377 0.2389 0.089 Uiso 1 1 calc R . . H12C H 0.3701 0.5651 0.2983 0.089 Uiso 1 1 calc R . . C13 C 0.5115(5) 0.6964(4) 0.1552(3) 0.0683(15) Uani 1 1 d . . . H13A H 0.5946 0.7314 0.1518 0.102 Uiso 1 1 calc R . . H13B H 0.4402 0.7431 0.1465 0.102 Uiso 1 1 calc R . . H13C H 0.5085 0.6444 0.1156 0.102 Uiso 1 1 calc R . . C14 C 0.5878(4) 0.6301(3) 0.4495(2) 0.0343(8) Uani 1 1 d . . . C15 C 0.4514(4) 0.4952(3) 0.5217(2) 0.0408(10) Uani 1 1 d . . . H15 H 0.3934 0.5279 0.5605 0.049 Uiso 1 1 calc R . . C16 C 0.3669(5) 0.4445(3) 0.4608(3) 0.0466(11) Uani 1 1 d . . . H16A H 0.4228 0.4115 0.4218 0.056 Uiso 1 1 calc R . . H16B H 0.3130 0.4943 0.4337 0.056 Uiso 1 1 calc R . . C17 C 0.2784(5) 0.3672(3) 0.5009(3) 0.0618(14) Uani 1 1 d . . . H17A H 0.2178 0.4014 0.5365 0.074 Uiso 1 1 calc R . . H17B H 0.2262 0.3325 0.4611 0.074 Uiso 1 1 calc R . . C18 C 0.3589(6) 0.2913(3) 0.5469(3) 0.0611(13) Uani 1 1 d . . . H18A H 0.4104 0.2505 0.5104 0.073 Uiso 1 1 calc R . . H18B H 0.2997 0.2469 0.5758 0.073 Uiso 1 1 calc R . . C19 C 0.4517(6) 0.3435(4) 0.6047(3) 0.0629(14) Uani 1 1 d . . . H19A H 0.3997 0.3763 0.6456 0.075 Uiso 1 1 calc R . . H19B H 0.5074 0.2934 0.6301 0.075 Uiso 1 1 calc R . . C20 C 0.5386(6) 0.4212(4) 0.5642(3) 0.0554(12) Uani 1 1 d . . . H20A H 0.5924 0.4560 0.6032 0.066 Uiso 1 1 calc R . . H20B H 0.5974 0.3882 0.5268 0.066 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 0.02718(13) 0.02373(12) 0.03584(14) -0.00008(11) 0.00231(12) -0.00093(11) Br1 0.0587(3) 0.0443(3) 0.0729(3) 0.0116(2) 0.0197(3) -0.0130(2) Br2 0.0599(3) 0.0378(2) 0.0535(3) -0.01130(19) -0.0009(2) 0.0025(2) N1 0.0291(17) 0.0320(16) 0.0340(16) -0.0040(13) -0.0008(13) 0.0011(14) N2 0.0278(17) 0.0351(18) 0.0375(17) -0.0034(14) -0.0003(14) 0.0003(14) N3 0.050(2) 0.0346(18) 0.0390(18) -0.0001(15) 0.0088(17) -0.0040(16) C1 0.0257(19) 0.0307(17) 0.0316(17) 0.0025(14) 0.0012(15) -0.0016(15) C2 0.035(2) 0.0314(19) 0.038(2) -0.0042(16) -0.0013(17) -0.0035(16) C3 0.041(2) 0.037(2) 0.056(3) -0.0091(19) -0.004(2) 0.0054(19) C4 0.059(3) 0.043(2) 0.056(3) -0.016(2) 0.003(2) -0.001(2) C5 0.064(3) 0.054(3) 0.051(3) -0.020(2) 0.002(3) -0.012(3) C6 0.044(3) 0.054(3) 0.045(2) -0.007(2) -0.006(2) -0.008(2) C7 0.034(2) 0.038(2) 0.038(2) -0.0032(16) 0.0017(17) -0.0064(17) C8 0.0253(18) 0.0295(19) 0.040(2) -0.0003(15) -0.0072(15) 0.0040(15) C9 0.031(2) 0.057(3) 0.050(3) -0.015(2) 0.0008(19) -0.005(2) C10 0.054(3) 0.050(3) 0.056(3) 0.010(2) -0.015(2) 0.001(2) C11 0.032(2) 0.045(2) 0.047(2) 0.0005(19) -0.0060(17) 0.0027(18) C12 0.032(2) 0.081(4) 0.064(3) 0.012(3) -0.006(2) 0.000(2) C13 0.063(3) 0.073(4) 0.069(3) 0.031(3) -0.015(3) -0.003(3) C14 0.039(2) 0.0300(19) 0.034(2) -0.0043(16) 0.0043(17) 0.0004(17) C15 0.050(2) 0.031(2) 0.041(2) 0.0033(18) 0.017(2) -0.0037(18) C16 0.057(3) 0.035(2) 0.048(2) 0.0047(19) 0.005(2) 0.001(2) C17 0.062(3) 0.044(3) 0.080(4) 0.004(2) 0.007(3) -0.009(2) C18 0.078(3) 0.036(2) 0.069(3) 0.009(2) 0.018(3) -0.007(2) C19 0.086(4) 0.051(3) 0.051(3) 0.018(2) 0.011(3) 0.005(3) C20 0.072(3) 0.046(3) 0.048(3) 0.008(2) -0.002(2) -0.001(2) _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 C14 1.930(4) . ? Pd1 C1 1.979(4) . ? Pd1 Br1 2.4347(5) . ? Pd1 Br2 2.4556(5) . ? N1 C1 1.348(5) . ? N1 C2 1.398(5) . ? N1 C8 1.490(5) . ? N2 C1 1.324(5) . ? N2 C7 1.402(5) . ? N2 C11 1.486(5) . ? N3 C14 1.134(5) . ? N3 C15 1.459(5) . ? C2 C3 1.385(6) . ? C2 C7 1.395(6) . ? C3 C4 1.377(6) . ? C4 C5 1.408(7) . ? C5 C6 1.357(6) . ? C6 C7 1.390(6) . ? C8 C9 1.497(5) . ? C8 C10 1.518(5) . ? C11 C13 1.496(7) . ? C11 C12 1.504(6) . ? C15 C16 1.510(6) . ? C15 C20 1.517(6) . ? C16 C17 1.534(6) . ? C17 C18 1.525(7) . ? C18 C19 1.534(7) . ? C19 C20 1.531(7) . ? 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 C14 Pd1 C1 86.45(15) . . ? C14 Pd1 Br1 174.26(11) . . ? C1 Pd1 Br1 88.22(10) . . ? C14 Pd1 Br2 89.84(11) . . ? C1 Pd1 Br2 176.29(10) . . ? Br1 Pd1 Br2 95.49(2) . . ? C1 N1 C2 109.1(3) . . ? C1 N1 C8 123.1(3) . . ? C2 N1 C8 127.8(3) . . ? C1 N2 C7 109.9(3) . . ? C1 N2 C11 123.0(3) . . ? C7 N2 C11 127.0(3) . . ? C14 N3 C15 175.4(4) . . ? N2 C1 N1 108.8(3) . . ? N2 C1 Pd1 126.1(3) . . ? N1 C1 Pd1 125.0(3) . . ? C3 C2 C7 121.5(4) . . ? C3 C2 N1 132.1(4) . . ? C7 C2 N1 106.4(3) . . ? C4 C3 C2 117.4(4) . . ? C3 C4 C5 120.8(4) . . ? C6 C5 C4 121.8(4) . . ? C5 C6 C7 117.9(4) . . ? C6 C7 C2 120.6(4) . . ? C6 C7 N2 133.5(4) . . ? C2 C7 N2 105.9(3) . . ? N1 C8 C9 110.6(3) . . ? N1 C8 C10 110.1(3) . . ? C9 C8 C10 114.2(4) . . ? N2 C11 C13 110.1(4) . . ? N2 C11 C12 112.1(3) . . ? C13 C11 C12 113.8(4) . . ? N3 C14 Pd1 175.8(3) . . ? N3 C15 C16 109.0(3) . . ? N3 C15 C20 110.3(4) . . ? C16 C15 C20 111.7(3) . . ? C15 C16 C17 109.4(4) . . ? C18 C17 C16 111.3(4) . . ? C17 C18 C19 111.0(4) . . ? C20 C19 C18 112.1(4) . . ? C15 C20 C19 108.7(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.708 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.084 # Attachment 'cis-2b.cif' data_6008 _database_code_depnum_ccdc_archive 'CCDC 703033' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 Br2 N3 Pd' _chemical_formula_weight 551.65 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' Br Br -0.2901 2.4595 '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 10.1986(5) _cell_length_b 13.0958(6) _cell_length_c 16.2190(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2166.19(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7368 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.48 _exptl_crystal_description BLOCK _exptl_crystal_colour 'PALE YELLOW' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 4.550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2633 _exptl_absorpt_correction_T_max 0.5683 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 15395 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4938 _reflns_number_gt 4590 _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^)+(0.0159P)^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 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 0.041(5) _refine_ls_number_reflns 4938 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0256 _refine_ls_R_factor_gt 0.0227 _refine_ls_wR_factor_ref 0.0493 _refine_ls_wR_factor_gt 0.0487 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.18573(2) 0.297769(14) 0.896539(11) 0.02187(5) Uani 1 1 d . . . Br2 Br 0.17522(4) 0.14062(2) 0.980989(17) 0.03637(8) Uani 1 1 d . . . Br1 Br 0.30394(3) 0.21804(2) 0.782509(18) 0.04064(8) Uani 1 1 d . . . N1 N 0.1031(2) 0.45046(17) 0.77234(14) 0.0238(5) Uani 1 1 d . . . N2 N 0.2882(2) 0.49356(17) 0.82970(14) 0.0239(5) Uani 1 1 d . . . N3 N 0.0418(3) 0.42244(19) 1.02897(16) 0.0333(6) Uani 1 1 d . . . C1 C 0.1916(3) 0.42353(19) 0.82906(15) 0.0221(5) Uani 1 1 d . . . C2 C 0.1455(2) 0.5394(2) 0.73263(17) 0.0236(6) Uani 1 1 d . . . C3 C 0.0934(3) 0.5948(2) 0.66649(18) 0.0325(7) Uani 1 1 d . . . H3 H 0.0141 0.5769 0.6421 0.039 Uiso 1 1 calc R . . C4 C 0.1652(3) 0.6768(2) 0.63937(18) 0.0338(7) Uani 1 1 d . . . H4 H 0.1341 0.7148 0.5951 0.041 Uiso 1 1 calc R . . C5 C 0.2822(3) 0.7046(2) 0.67583(18) 0.0353(7) Uani 1 1 d . . . H5 H 0.3284 0.7602 0.6551 0.042 Uiso 1 1 calc R . . C6 C 0.3324(3) 0.6515(2) 0.74250(18) 0.0313(6) Uani 1 1 d . . . H6 H 0.4096 0.6716 0.7683 0.038 Uiso 1 1 calc R . . C7 C 0.2627(3) 0.5672(2) 0.76916(17) 0.0250(6) Uani 1 1 d . . . C8 C -0.0170(3) 0.3908(2) 0.75451(19) 0.0289(6) Uani 1 1 d . . . H8 H -0.0190 0.3342 0.7940 0.035 Uiso 1 1 calc R . . C9 C -0.1387(3) 0.4541(3) 0.7701(3) 0.0513(10) Uani 1 1 d . . . H9A H -0.1428 0.4724 0.8273 0.077 Uiso 1 1 calc R . . H9B H -0.2151 0.4152 0.7556 0.077 Uiso 1 1 calc R . . H9C H -0.1355 0.5150 0.7371 0.077 Uiso 1 1 calc R . . C10 C -0.0108(4) 0.3438(3) 0.6697(2) 0.0552(10) Uani 1 1 d . . . H10A H -0.0172 0.3966 0.6288 0.083 Uiso 1 1 calc R . . H10B H -0.0822 0.2967 0.6631 0.083 Uiso 1 1 calc R . . H10C H 0.0708 0.3083 0.6633 0.083 Uiso 1 1 calc R . . C11 C 0.4056(3) 0.4859(2) 0.88231(17) 0.0273(6) Uani 1 1 d . . . H11 H 0.3963 0.4239 0.9156 0.033 Uiso 1 1 calc R . . C12 C 0.5278(3) 0.4729(3) 0.82966(19) 0.0376(8) Uani 1 1 d . . . H12A H 0.5146 0.4180 0.7913 0.056 Uiso 1 1 calc R . . H12B H 0.6013 0.4576 0.8645 0.056 Uiso 1 1 calc R . . H12C H 0.5445 0.5349 0.7999 0.056 Uiso 1 1 calc R . . C13 C 0.4138(4) 0.5754(3) 0.9417(2) 0.0503(10) Uani 1 1 d . . . H13A H 0.4254 0.6375 0.9111 0.075 Uiso 1 1 calc R . . H13B H 0.4869 0.5659 0.9782 0.075 Uiso 1 1 calc R . . H13C H 0.3344 0.5794 0.9733 0.075 Uiso 1 1 calc R . . C14 C 0.0934(3) 0.3740(2) 0.98102(17) 0.0272(6) Uani 1 1 d . . . C15 C -0.0206(4) 0.4868(3) 1.08964(19) 0.0416(8) Uani 1 1 d . . . H15A H 0.0060 0.4657 1.1445 0.050 Uiso 1 1 calc R . . H15B H -0.1150 0.4796 1.0856 0.050 Uiso 1 1 calc R . . C16 C 0.0179(4) 0.5995(3) 1.0759(2) 0.0575(11) Uani 1 1 d . . . H16A H -0.0205 0.6405 1.1195 0.069 Uiso 1 1 calc R . . H16B H 0.1124 0.6056 1.0802 0.069 Uiso 1 1 calc R . . C17 C -0.0242(4) 0.6419(3) 0.9949(3) 0.0636(12) Uani 1 1 d . . . H17A H 0.0148 0.6013 0.9514 0.076 Uiso 1 1 calc R . . H17B H 0.0096 0.7109 0.9898 0.076 Uiso 1 1 calc R . . C18 C -0.1726(5) 0.6445(3) 0.9822(3) 0.0924(16) Uani 1 1 d . . . H18A H -0.2061 0.5760 0.9814 0.139 Uiso 1 1 calc R . . H18B H -0.1922 0.6774 0.9307 0.139 Uiso 1 1 calc R . . H18C H -0.2129 0.6818 1.0264 0.139 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 0.02652(9) 0.01653(9) 0.02254(9) 0.00242(8) 0.00084(9) -0.00040(10) Br2 0.05277(18) 0.02414(15) 0.03220(15) 0.00643(11) -0.00320(16) -0.00516(16) Br1 0.05167(19) 0.03106(16) 0.03920(16) -0.00173(13) 0.01166(15) 0.00913(17) N1 0.0240(11) 0.0208(12) 0.0264(12) 0.0036(10) -0.0001(10) 0.0004(10) N2 0.0254(12) 0.0183(11) 0.0279(12) 0.0029(9) -0.0022(9) 0.0003(10) N3 0.0426(15) 0.0254(14) 0.0320(14) 0.0030(11) 0.0032(12) 0.0030(12) C1 0.0209(12) 0.0216(13) 0.0239(12) -0.0001(10) 0.0021(12) 0.0038(13) C2 0.0209(13) 0.0203(14) 0.0295(14) 0.0068(11) 0.0038(11) 0.0021(11) C3 0.0303(15) 0.0344(18) 0.0327(16) 0.0082(13) 0.0016(13) 0.0049(14) C4 0.0365(17) 0.0276(16) 0.0373(15) 0.0149(12) 0.0029(14) 0.0120(14) C5 0.0415(17) 0.0202(15) 0.0442(17) 0.0096(14) 0.0132(13) 0.0054(14) C6 0.0317(15) 0.0224(14) 0.0398(16) 0.0024(12) 0.0069(14) 0.0001(14) C7 0.0279(14) 0.0181(14) 0.0291(15) 0.0025(12) 0.0018(12) 0.0031(12) C8 0.0246(13) 0.0289(16) 0.0332(16) 0.0040(12) -0.0025(12) -0.0052(13) C9 0.0271(16) 0.049(2) 0.078(3) 0.003(2) 0.0045(17) 0.0018(16) C10 0.054(2) 0.063(3) 0.048(2) -0.0141(19) -0.0050(18) -0.015(2) C11 0.0273(14) 0.0261(15) 0.0285(15) 0.0041(12) -0.0052(12) -0.0009(13) C12 0.0290(16) 0.043(2) 0.0406(18) 0.0113(15) -0.0029(14) 0.0030(15) C13 0.059(2) 0.049(2) 0.044(2) -0.0117(17) -0.0107(18) -0.003(2) C14 0.0332(14) 0.0233(15) 0.0252(14) 0.0058(12) 0.0019(13) 0.0017(13) C15 0.055(2) 0.0409(19) 0.0289(17) 0.0006(14) 0.0112(15) 0.0106(17) C16 0.076(3) 0.038(2) 0.058(2) -0.0134(18) 0.008(2) 0.000(2) C17 0.093(3) 0.028(2) 0.070(3) 0.0058(19) 0.017(2) -0.001(2) C18 0.101(4) 0.061(3) 0.115(4) 0.029(3) -0.008(4) -0.009(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 C14 1.939(3) . ? Pd1 C1 1.978(3) . ? Pd1 Br1 2.4422(4) . ? Pd1 Br2 2.4745(3) . ? N1 C1 1.336(3) . ? N1 C2 1.399(3) . ? N1 C8 1.481(3) . ? N2 C1 1.346(3) . ? N2 C7 1.400(3) . ? N2 C11 1.474(3) . ? N3 C14 1.133(4) . ? N3 C15 1.444(4) . ? C2 C7 1.383(4) . ? C2 C3 1.400(4) . ? C3 C4 1.372(4) . ? C4 C5 1.381(4) . ? C5 C6 1.384(4) . ? C6 C7 1.382(4) . ? C8 C10 1.508(5) . ? C8 C9 1.514(4) . ? C11 C13 1.520(4) . ? C11 C12 1.520(4) . ? C15 C16 1.543(5) . ? C16 C17 1.488(5) . ? C17 C18 1.528(6) . ? 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 C14 Pd1 C1 88.68(11) . . ? C14 Pd1 Br1 174.19(8) . . ? C1 Pd1 Br1 85.53(7) . . ? C14 Pd1 Br2 90.92(8) . . ? C1 Pd1 Br2 179.25(8) . . ? Br1 Pd1 Br2 94.874(13) . . ? C1 N1 C2 109.2(2) . . ? C1 N1 C8 123.6(2) . . ? C2 N1 C8 127.2(2) . . ? C1 N2 C7 109.1(2) . . ? C1 N2 C11 123.6(2) . . ? C7 N2 C11 127.1(2) . . ? C14 N3 C15 178.0(3) . . ? N1 C1 N2 108.6(2) . . ? N1 C1 Pd1 125.5(2) . . ? N2 C1 Pd1 125.81(19) . . ? C7 C2 N1 106.8(2) . . ? C7 C2 C3 121.3(3) . . ? N1 C2 C3 131.9(3) . . ? C4 C3 C2 116.7(3) . . ? C3 C4 C5 122.0(3) . . ? C4 C5 C6 121.4(3) . . ? C7 C6 C5 117.1(3) . . ? C6 C7 C2 121.4(3) . . ? C6 C7 N2 132.3(3) . . ? C2 C7 N2 106.2(2) . . ? N1 C8 C10 111.0(2) . . ? N1 C8 C9 110.9(2) . . ? C10 C8 C9 114.2(3) . . ? N2 C11 C13 111.0(2) . . ? N2 C11 C12 110.4(2) . . ? C13 C11 C12 113.4(3) . . ? N3 C14 Pd1 176.9(3) . . ? N3 C15 C16 110.4(3) . . ? C17 C16 C15 114.3(3) . . ? C16 C17 C18 114.4(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.542 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.068 # Attachment 'trans-2a.cif' data_8552a _database_code_depnum_ccdc_archive 'CCDC 703034' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 Br2 N3 Pd' _chemical_formula_weight 577.68 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' Br Br -0.2901 2.4595 '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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.2666(17) _cell_length_b 10.6396(12) _cell_length_c 14.0629(16) _cell_angle_alpha 90.00 _cell_angle_beta 96.277(3) _cell_angle_gamma 90.00 _cell_volume 2270.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2021 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 21.91 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 4.346 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1946 _exptl_absorpt_correction_T_max 0.5431 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 15491 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0896 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5208 _reflns_number_gt 3547 _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^)+(0.0579P)^2^+22.7866P] 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 5208 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1143 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.2014 _refine_ls_wR_factor_gt 0.1891 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 0.73359(5) 0.77789(6) 0.11945(5) 0.0288(2) Uani 1 1 d . . . Br1 Br 0.87891(9) 0.69491(13) 0.10894(14) 0.0736(5) Uani 1 1 d . . . Br2 Br 0.58105(7) 0.84132(9) 0.12347(8) 0.0399(3) Uani 1 1 d . . . N1 N 0.6747(5) 0.5263(6) 0.0427(5) 0.0240(16) Uani 1 1 d . . . N2 N 0.6850(5) 0.5319(7) 0.1989(5) 0.0262(16) Uani 1 1 d . . . N3 N 0.8118(6) 1.0521(8) 0.1251(6) 0.041(2) Uani 1 1 d . . . C1 C 0.6931(6) 0.6007(8) 0.1201(6) 0.0264(19) Uani 1 1 d . . . C2 C 0.6537(6) 0.4055(8) 0.0722(6) 0.0236(18) Uani 1 1 d . . . C3 C 0.6272(7) 0.2962(8) 0.0226(7) 0.033(2) Uani 1 1 d . . . H3 H 0.6202 0.2935 -0.0446 0.040 Uiso 1 1 calc R . . C4 C 0.6116(7) 0.1921(9) 0.0768(7) 0.036(2) Uani 1 1 d . . . H4 H 0.5950 0.1164 0.0454 0.043 Uiso 1 1 calc R . . C5 C 0.6196(7) 0.1954(9) 0.1756(8) 0.040(3) Uani 1 1 d . . . H5 H 0.6085 0.1220 0.2094 0.048 Uiso 1 1 calc R . . C6 C 0.6432(7) 0.3021(9) 0.2252(7) 0.033(2) Uani 1 1 d . . . H6 H 0.6477 0.3034 0.2924 0.039 Uiso 1 1 calc R . . C7 C 0.6604(6) 0.4093(8) 0.1735(6) 0.028(2) Uani 1 1 d . . . C8 C 0.6710(7) 0.5713(9) -0.0574(6) 0.033(2) Uani 1 1 d . . . H8 H 0.6869 0.6615 -0.0540 0.039 Uiso 1 1 calc R . . C10 C 0.7394(8) 0.5070(12) -0.1097(8) 0.051(3) Uani 1 1 d . . . H10A H 0.7978 0.5305 -0.0810 0.076 Uiso 1 1 calc R . . H10B H 0.7322 0.5324 -0.1764 0.076 Uiso 1 1 calc R . . H10C H 0.7324 0.4166 -0.1055 0.076 Uiso 1 1 calc R . . C11 C 0.6963(7) 0.5860(10) 0.2973(6) 0.038(2) Uani 1 1 d . . . H11 H 0.7096 0.6763 0.2899 0.046 Uiso 1 1 calc R . . C12 C 0.7738(11) 0.5310(15) 0.3545(9) 0.078(5) Uani 1 1 d . . . H12A H 0.8222 0.5248 0.3154 0.117 Uiso 1 1 calc R . . H12B H 0.7590 0.4480 0.3762 0.117 Uiso 1 1 calc R . . H12C H 0.7910 0.5843 0.4093 0.117 Uiso 1 1 calc R . . C14 C 0.7837(7) 0.9538(8) 0.1237(6) 0.030(2) Uani 1 1 d . . . C15 C 0.8478(7) 1.1785(9) 0.1279(8) 0.039(2) Uani 1 1 d . . . H14 H 0.7983 1.2390 0.1212 0.047 Uiso 1 1 calc R . . C13 C 0.9022(11) 1.1983(13) 0.0468(11) 0.077(5) Uani 1 1 d . . . H15A H 0.8662 1.1831 -0.0142 0.092 Uiso 1 1 calc R . . H15B H 0.9516 1.1389 0.0520 0.092 Uiso 1 1 calc R . . C16 C 0.9367(12) 1.3310(14) 0.0496(11) 0.083(5) Uani 1 1 d . . . H16A H 0.9712 1.3442 -0.0044 0.100 Uiso 1 1 calc R . . H16B H 0.8869 1.3897 0.0427 0.100 Uiso 1 1 calc R . . C17 C 0.9926(9) 1.3578(13) 0.1401(13) 0.078(5) Uani 1 1 d . . . H17A H 1.0127 1.4453 0.1406 0.093 Uiso 1 1 calc R . . H17B H 1.0446 1.3031 0.1456 0.093 Uiso 1 1 calc R . . C18 C 0.9390(10) 1.3346(12) 0.2248(11) 0.073(4) Uani 1 1 d . . . H18A H 0.9769 1.3465 0.2850 0.087 Uiso 1 1 calc R . . H18B H 0.8906 1.3954 0.2228 0.087 Uiso 1 1 calc R . . C19 C 0.9018(10) 1.2022(11) 0.2208(9) 0.060(4) Uani 1 1 d . . . H19A H 0.9503 1.1415 0.2292 0.072 Uiso 1 1 calc R . . H19B H 0.8653 1.1904 0.2733 0.072 Uiso 1 1 calc R . . C20 C 0.6116(9) 0.5800(11) 0.3421(8) 0.057(3) Uani 1 1 d . . . H20A H 0.5659 0.6244 0.3020 0.086 Uiso 1 1 calc R . . H20B H 0.6197 0.6188 0.4048 0.086 Uiso 1 1 calc R . . H20C H 0.5944 0.4929 0.3483 0.086 Uiso 1 1 calc R . . C21 C 0.5776(8) 0.5640(11) -0.1056(7) 0.047(3) Uani 1 1 d . . . H21A H 0.5581 0.4772 -0.1077 0.070 Uiso 1 1 calc R . . H21B H 0.5756 0.5965 -0.1702 0.070 Uiso 1 1 calc R . . H21C H 0.5392 0.6137 -0.0698 0.070 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 0.0411(5) 0.0201(3) 0.0248(4) -0.0017(3) 0.0019(3) -0.0050(3) Br1 0.0421(8) 0.0516(8) 0.1265(14) -0.0169(8) 0.0071(8) -0.0015(6) Br2 0.0482(7) 0.0284(5) 0.0433(6) -0.0031(4) 0.0057(5) 0.0028(4) N1 0.040(5) 0.019(3) 0.012(3) 0.001(3) -0.002(3) -0.004(3) N2 0.040(5) 0.024(4) 0.014(3) 0.001(3) 0.000(3) -0.002(3) N3 0.049(6) 0.036(5) 0.037(5) 0.003(4) 0.000(4) -0.005(4) C1 0.032(5) 0.021(4) 0.026(5) -0.007(4) 0.006(4) 0.002(4) C2 0.030(5) 0.016(4) 0.024(4) 0.000(3) -0.002(4) 0.003(3) C3 0.047(6) 0.023(5) 0.028(5) -0.005(4) 0.000(4) 0.003(4) C4 0.046(6) 0.020(5) 0.039(6) -0.005(4) -0.005(5) -0.001(4) C5 0.050(7) 0.023(5) 0.048(6) 0.009(4) 0.006(5) 0.000(4) C6 0.039(6) 0.031(5) 0.027(5) 0.008(4) -0.001(4) 0.003(4) C7 0.036(5) 0.026(5) 0.023(5) 0.005(4) 0.000(4) 0.000(4) C8 0.052(6) 0.033(5) 0.015(4) 0.002(4) 0.012(4) 0.004(4) C10 0.062(8) 0.055(7) 0.038(6) -0.002(5) 0.017(6) 0.007(6) C11 0.052(7) 0.046(6) 0.018(5) -0.003(4) 0.007(4) -0.002(5) C12 0.104(12) 0.079(10) 0.045(8) -0.019(7) -0.019(8) 0.003(9) C14 0.043(6) 0.020(5) 0.027(5) -0.005(4) 0.003(4) -0.009(4) C15 0.040(6) 0.026(5) 0.051(7) -0.001(4) 0.005(5) -0.003(4) C13 0.103(12) 0.056(9) 0.077(10) -0.002(7) 0.033(9) -0.034(8) C16 0.119(14) 0.064(10) 0.075(11) 0.005(8) 0.045(10) -0.032(9) C17 0.051(8) 0.041(7) 0.138(16) 0.003(8) -0.009(9) -0.015(6) C18 0.080(11) 0.049(8) 0.084(11) -0.025(7) -0.014(9) -0.015(7) C19 0.083(10) 0.040(7) 0.055(8) 0.016(6) -0.005(7) -0.008(6) C20 0.092(10) 0.041(7) 0.043(7) -0.013(5) 0.027(7) -0.008(6) C21 0.054(7) 0.055(7) 0.029(5) 0.006(5) -0.001(5) 0.008(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 C1 1.984(9) . ? Pd1 C14 2.020(9) . ? Pd1 Br1 2.4072(16) . ? Pd1 Br2 2.4312(14) . ? N1 C1 1.350(11) . ? N1 C2 1.398(11) . ? N1 C8 1.482(11) . ? N2 C1 1.346(11) . ? N2 C7 1.393(11) . ? N2 C11 1.492(11) . ? N3 C14 1.130(12) . ? N3 C15 1.452(13) . ? C2 C3 1.394(12) . ? C2 C7 1.417(12) . ? C3 C4 1.379(13) . ? C4 C5 1.382(15) . ? C5 C6 1.360(14) . ? C6 C7 1.394(13) . ? C8 C10 1.506(14) . ? C8 C21 1.513(15) . ? C11 C12 1.475(17) . ? C11 C20 1.500(15) . ? C15 C19 1.488(16) . ? C15 C13 1.498(17) . ? C13 C16 1.506(18) . ? C16 C17 1.48(2) . ? C17 C18 1.54(2) . ? C18 C19 1.517(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 C14 175.7(4) . . ? C1 Pd1 Br1 86.7(3) . . ? C14 Pd1 Br1 89.6(3) . . ? C1 Pd1 Br2 87.9(3) . . ? C14 Pd1 Br2 95.9(3) . . ? Br1 Pd1 Br2 174.15(5) . . ? C1 N1 C2 109.5(7) . . ? C1 N1 C8 124.0(7) . . ? C2 N1 C8 126.4(7) . . ? C1 N2 C7 110.1(7) . . ? C1 N2 C11 122.9(7) . . ? C7 N2 C11 126.9(8) . . ? C14 N3 C15 179.4(11) . . ? N2 C1 N1 108.4(7) . . ? N2 C1 Pd1 125.3(6) . . ? N1 C1 Pd1 126.2(6) . . ? C3 C2 N1 133.0(8) . . ? C3 C2 C7 120.8(8) . . ? N1 C2 C7 106.2(7) . . ? C4 C3 C2 116.9(9) . . ? C3 C4 C5 122.2(9) . . ? C6 C5 C4 121.8(9) . . ? C5 C6 C7 118.0(9) . . ? N2 C7 C6 133.9(9) . . ? N2 C7 C2 105.8(7) . . ? C6 C7 C2 120.3(9) . . ? N1 C8 C10 111.2(8) . . ? N1 C8 C21 110.2(8) . . ? C10 C8 C21 115.3(9) . . ? C12 C11 N2 110.9(9) . . ? C12 C11 C20 115.5(11) . . ? N2 C11 C20 110.8(9) . . ? N3 C14 Pd1 179.4(9) . . ? N3 C15 C19 110.6(9) . . ? N3 C15 C13 110.4(9) . . ? C19 C15 C13 110.2(11) . . ? C15 C13 C16 109.4(12) . . ? C17 C16 C13 111.7(13) . . ? C16 C17 C18 109.2(12) . . ? C19 C18 C17 110.4(11) . . ? C15 C19 C18 111.0(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.723 _refine_diff_density_min -1.330 _refine_diff_density_rms 0.178 # Attachment 'trans-2c.cif' data_6007 _database_code_depnum_ccdc_archive 'CCDC 703035' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H27 Br2 N3 Pd' _chemical_formula_weight 599.69 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' Br Br -0.2901 2.4595 '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 8.8532(4) _cell_length_b 10.2693(4) _cell_length_c 14.0845(6) _cell_angle_alpha 79.1370(10) _cell_angle_beta 77.3210(10) _cell_angle_gamma 70.0450(10) _cell_volume 1165.24(9) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6136 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.50 _exptl_crystal_description BLOCK _exptl_crystal_colour 'PALE YELLOW' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.709 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 4.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2820 _exptl_absorpt_correction_T_max 0.5884 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 15312 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5358 _reflns_number_gt 4567 _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^)+(0.0344P)^2^+0.2461P] 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 5358 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.693690(18) 0.611131(16) 0.240580(11) 0.03135(6) Uani 1 1 d . . . Br1 Br 0.65113(3) 0.41765(3) 0.18621(2) 0.04388(8) Uani 1 1 d . . . Br2 Br 0.74086(4) 0.79542(3) 0.30400(2) 0.05591(9) Uani 1 1 d . . . N1 N 1.0403(2) 0.44293(18) 0.24640(12) 0.0309(4) Uani 1 1 d . . . N2 N 0.8851(2) 0.39272(19) 0.38152(13) 0.0334(4) Uani 1 1 d . . . N3 N 0.4010(2) 0.82975(19) 0.14727(15) 0.0393(4) Uani 1 1 d . . . C1 C 0.8855(2) 0.4745(2) 0.29446(15) 0.0309(4) Uani 1 1 d . . . C2 C 1.1422(2) 0.3376(2) 0.30338(15) 0.0314(4) Uani 1 1 d . . . C3 C 1.3096(3) 0.2691(2) 0.28715(17) 0.0393(5) Uani 1 1 d . . . H3 H 1.3768 0.2910 0.2289 0.047 Uiso 1 1 calc R . . C4 C 1.3725(3) 0.1678(3) 0.36035(19) 0.0459(6) Uani 1 1 d . . . H4 H 1.4847 0.1188 0.3514 0.055 Uiso 1 1 calc R . . C5 C 1.2741(3) 0.1369(3) 0.44658(18) 0.0464(6) Uani 1 1 d . . . H5 H 1.3215 0.0679 0.4950 0.056 Uiso 1 1 calc R . . C6 C 1.1083(3) 0.2044(2) 0.46362(17) 0.0399(5) Uani 1 1 d . . . H6 H 1.0421 0.1830 0.5224 0.048 Uiso 1 1 calc R . . C7 C 1.0434(3) 0.3057(2) 0.38970(15) 0.0322(4) Uani 1 1 d . . . C11 C 0.7366(3) 0.4006(3) 0.45594(16) 0.0398(5) Uani 1 1 d . . . H8 H 0.6452 0.4725 0.4278 0.048 Uiso 1 1 calc R . . C9 C 0.7496(3) 0.4512(3) 0.54733(18) 0.0536(7) Uani 1 1 d . . . H9A H 0.8425 0.3864 0.5750 0.080 Uiso 1 1 calc R . . H9B H 0.6509 0.4567 0.5950 0.080 Uiso 1 1 calc R . . H9C H 0.7637 0.5429 0.5304 0.080 Uiso 1 1 calc R . . C10 C 0.6982(3) 0.2649(3) 0.4739(2) 0.0543(7) Uani 1 1 d . . . H10A H 0.6912 0.2404 0.4122 0.081 Uiso 1 1 calc R . . H10B H 0.5950 0.2752 0.5180 0.081 Uiso 1 1 calc R . . H10C H 0.7838 0.1917 0.5033 0.081 Uiso 1 1 calc R . . C8 C 1.0903(3) 0.5184(2) 0.15098(15) 0.0353(5) Uani 1 1 d . . . H11 H 0.9893 0.5824 0.1283 0.042 Uiso 1 1 calc R . . C12 C 1.1765(4) 0.4213(3) 0.07452(19) 0.0594(7) Uani 1 1 d . . . H12A H 1.2789 0.3592 0.0928 0.089 Uiso 1 1 calc R . . H12B H 1.1977 0.4753 0.0116 0.089 Uiso 1 1 calc R . . H12C H 1.1086 0.3668 0.0698 0.089 Uiso 1 1 calc R . . C13 C 1.1866(3) 0.6084(3) 0.1643(2) 0.0496(6) Uani 1 1 d . . . H13A H 1.1186 0.6773 0.2073 0.074 Uiso 1 1 calc R . . H13B H 1.2216 0.6553 0.1010 0.074 Uiso 1 1 calc R . . H13C H 1.2814 0.5502 0.1930 0.074 Uiso 1 1 calc R . . C14 C 0.5062(3) 0.7486(2) 0.18162(17) 0.0394(5) Uani 1 1 d . . . C15 C 0.2686(3) 0.9366(2) 0.11355(17) 0.0338(5) Uani 1 1 d . . . C16 C 0.2719(3) 0.9729(2) 0.01286(18) 0.0392(5) Uani 1 1 d . . . C17 C 0.1416(3) 1.0852(3) -0.01629(19) 0.0472(6) Uani 1 1 d . . . H17 H 0.1395 1.1158 -0.0834 0.057 Uiso 1 1 calc R . . C18 C 0.0166(3) 1.1510(3) 0.0525(2) 0.0516(7) Uani 1 1 d . . . H18 H -0.0702 1.2264 0.0317 0.062 Uiso 1 1 calc R . . C19 C 0.0156(3) 1.1092(3) 0.1508(2) 0.0499(6) Uani 1 1 d . . . H19 H -0.0727 1.1549 0.1962 0.060 Uiso 1 1 calc R . . C20 C 0.1421(3) 1.0012(2) 0.18391(17) 0.0394(5) Uani 1 1 d . . . C21 C 0.4060(3) 0.8941(3) -0.0602(2) 0.0550(7) Uani 1 1 d . . . H21A H 0.5106 0.8852 -0.0443 0.082 Uiso 1 1 calc R . . H21B H 0.3971 0.9441 -0.1254 0.082 Uiso 1 1 calc R . . H21C H 0.3972 0.8020 -0.0580 0.082 Uiso 1 1 calc R . . C22 C 0.1425(4) 0.9539(3) 0.29154(19) 0.0594(7) Uani 1 1 d . . . H22A H 0.0404 1.0053 0.3287 0.089 Uiso 1 1 calc R . . H22B H 0.2322 0.9708 0.3107 0.089 Uiso 1 1 calc R . . H22C H 0.1552 0.8549 0.3047 0.089 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 0.02675(9) 0.03059(10) 0.03186(10) 0.00182(7) -0.00809(6) -0.00386(7) Br1 0.03549(13) 0.03875(14) 0.05820(16) -0.00473(11) -0.01308(11) -0.01010(10) Br2 0.06938(19) 0.04403(15) 0.05658(17) -0.01359(12) -0.02291(14) -0.00908(13) N1 0.0269(8) 0.0351(9) 0.0287(9) 0.0038(7) -0.0070(7) -0.0095(7) N2 0.0305(9) 0.0354(10) 0.0301(9) 0.0033(7) -0.0071(7) -0.0077(8) N3 0.0364(10) 0.0313(10) 0.0500(12) 0.0004(8) -0.0160(9) -0.0080(8) C1 0.0293(10) 0.0323(11) 0.0305(10) 0.0000(8) -0.0082(8) -0.0088(8) C2 0.0301(10) 0.0313(11) 0.0325(10) 0.0013(8) -0.0111(8) -0.0084(9) C3 0.0307(11) 0.0432(13) 0.0412(12) -0.0029(10) -0.0071(9) -0.0086(10) C4 0.0313(12) 0.0443(14) 0.0564(15) -0.0067(11) -0.0173(11) 0.0016(10) C5 0.0502(14) 0.0398(13) 0.0454(14) 0.0043(11) -0.0244(12) -0.0043(11) C6 0.0457(13) 0.0383(12) 0.0326(11) 0.0042(9) -0.0132(10) -0.0095(10) C7 0.0308(11) 0.0325(11) 0.0326(11) 0.0000(9) -0.0111(9) -0.0076(9) C11 0.0299(11) 0.0482(14) 0.0325(11) 0.0040(10) -0.0016(9) -0.0082(10) C9 0.0509(15) 0.0631(17) 0.0391(14) -0.0084(12) 0.0008(11) -0.0119(13) C10 0.0506(15) 0.0656(18) 0.0471(15) 0.0066(13) -0.0038(12) -0.0287(14) C8 0.0315(11) 0.0410(12) 0.0308(11) 0.0072(9) -0.0064(9) -0.0135(9) C12 0.076(2) 0.0603(18) 0.0371(14) -0.0033(12) 0.0003(13) -0.0234(16) C13 0.0499(15) 0.0461(14) 0.0581(16) 0.0129(12) -0.0196(12) -0.0255(12) C14 0.0376(12) 0.0359(12) 0.0427(13) -0.0001(10) -0.0118(10) -0.0083(10) C15 0.0342(11) 0.0242(10) 0.0444(12) 0.0038(9) -0.0180(10) -0.0080(9) C16 0.0402(12) 0.0378(12) 0.0439(13) -0.0014(10) -0.0109(10) -0.0172(10) C17 0.0584(16) 0.0441(14) 0.0447(14) 0.0091(11) -0.0265(12) -0.0198(12) C18 0.0461(14) 0.0368(13) 0.0682(18) 0.0026(12) -0.0253(13) -0.0034(11) C19 0.0456(14) 0.0356(13) 0.0613(17) -0.0075(12) -0.0098(12) -0.0025(11) C20 0.0448(13) 0.0294(11) 0.0441(13) -0.0022(9) -0.0128(10) -0.0098(10) C21 0.0539(16) 0.0579(17) 0.0544(16) -0.0091(13) -0.0040(13) -0.0212(13) C22 0.082(2) 0.0511(16) 0.0411(14) -0.0047(12) -0.0101(14) -0.0165(15) _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 1.992(2) . ? Pd1 C14 2.000(2) . ? Pd1 Br1 2.4263(3) . ? Pd1 Br2 2.4278(3) . ? N1 C1 1.347(3) . ? N1 C2 1.398(3) . ? N1 C8 1.477(2) . ? N2 C1 1.349(3) . ? N2 C7 1.398(3) . ? N2 C11 1.479(3) . ? N3 C14 1.145(3) . ? N3 C15 1.405(3) . ? C2 C7 1.389(3) . ? C2 C3 1.394(3) . ? C3 C4 1.381(3) . ? C4 C5 1.384(4) . ? C5 C6 1.381(3) . ? C6 C7 1.394(3) . ? C11 C10 1.509(4) . ? C11 C9 1.516(3) . ? C8 C12 1.504(3) . ? C8 C13 1.513(3) . ? C15 C20 1.389(3) . ? C15 C16 1.393(3) . ? C16 C17 1.396(3) . ? C16 C21 1.498(3) . ? C17 C18 1.374(4) . ? C18 C19 1.369(4) . ? C19 C20 1.374(3) . ? C20 C22 1.503(3) . ? 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 C14 177.89(9) . . ? C1 Pd1 Br1 88.03(6) . . ? C14 Pd1 Br1 91.71(7) . . ? C1 Pd1 Br2 89.23(6) . . ? C14 Pd1 Br2 91.11(7) . . ? Br1 Pd1 Br2 176.503(10) . . ? C1 N1 C2 109.70(17) . . ? C1 N1 C8 123.28(17) . . ? C2 N1 C8 126.89(17) . . ? C1 N2 C7 109.77(17) . . ? C1 N2 C11 123.35(17) . . ? C7 N2 C11 126.86(17) . . ? C14 N3 C15 174.1(2) . . ? N1 C1 N2 107.75(17) . . ? N1 C1 Pd1 124.86(15) . . ? N2 C1 Pd1 127.32(15) . . ? C7 C2 C3 121.37(19) . . ? C7 C2 N1 106.52(17) . . ? C3 C2 N1 132.1(2) . . ? C4 C3 C2 117.1(2) . . ? C3 C4 C5 121.5(2) . . ? C6 C5 C4 121.9(2) . . ? C5 C6 C7 117.0(2) . . ? C2 C7 C6 121.1(2) . . ? C2 C7 N2 106.26(17) . . ? C6 C7 N2 132.6(2) . . ? N2 C11 C10 110.8(2) . . ? N2 C11 C9 110.58(19) . . ? C10 C11 C9 114.7(2) . . ? N1 C8 C12 111.91(19) . . ? N1 C8 C13 110.08(19) . . ? C12 C8 C13 113.7(2) . . ? N3 C14 Pd1 178.2(2) . . ? C20 C15 C16 123.9(2) . . ? C20 C15 N3 117.2(2) . . ? C16 C15 N3 118.9(2) . . ? C15 C16 C17 116.3(2) . . ? C15 C16 C21 121.9(2) . . ? C17 C16 C21 121.8(2) . . ? C18 C17 C16 120.4(2) . . ? C19 C18 C17 121.5(2) . . ? C18 C19 C20 120.8(2) . . ? C19 C20 C15 117.1(2) . . ? C19 C20 C22 121.4(2) . . ? C15 C20 C22 121.5(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.901 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.068