# 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 'Helene Olivier Bourbigou' _publ_contact_author_email HELENE.OLIVIER-BOURBIGOU@IFP.FR _publ_section_title ; Direct synthesis of a new class of N,N,N ligands based on 1,2-dihydro-1,10-phenanthroline backbone and their coordination to Pd complexes. ; loop_ _publ_author_name 'Helene Olivier Bourbigou' 'Pierre Braunstein' 'David Proriol' 'Claudine Rangheard' # Attachment 'CIF__reviewed_B817726K.txt' data_Ligand1 _database_code_depnum_ccdc_archive 'CCDC 701153' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N3' _chemical_formula_sum 'C19 H19 N3' _chemical_formula_weight 289.37 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.6143(4) _cell_length_b 16.7777(9) _cell_length_c 12.7282(5) _cell_angle_alpha 90.00 _cell_angle_beta 120.663(3) _cell_angle_gamma 90.00 _cell_volume 1582.38(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5595 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _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 10877 _diffrn_reflns_av_R_equivalents 0.0844 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 30.01 _reflns_number_total 4598 _reflns_number_gt 3097 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0875P)^2^+0.3630P] 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 4598 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1873 _refine_ls_wR_factor_gt 0.1654 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1991(2) -0.20678(11) 0.52034(15) 0.0368(4) Uani 1 1 d . . . H1 H 0.1204 -0.2360 0.5377 0.044 Uiso 1 1 calc R . . C2 C 0.3647(2) -0.18170(12) 0.61912(16) 0.0399(4) Uani 1 1 d . . . H2 H 0.3953 -0.1933 0.7005 0.048 Uiso 1 1 calc R . . C3 C 0.4808(2) -0.14057(11) 0.59697(15) 0.0364(4) Uani 1 1 d . . . H3 H 0.5931 -0.1227 0.6630 0.044 Uiso 1 1 calc R . . C4 C 0.43381(19) -0.12451(9) 0.47519(14) 0.0288(3) Uani 1 1 d . . . C5 C 0.5489(2) -0.08363(10) 0.44462(16) 0.0346(4) Uani 1 1 d . . . H5 H 0.6634 -0.0652 0.5073 0.042 Uiso 1 1 calc R . . C6 C 0.4954(2) -0.07061(11) 0.32476(17) 0.0372(4) Uani 1 1 d . . . H6 H 0.5742 -0.0442 0.3044 0.045 Uiso 1 1 calc R . . C7 C 0.3238(2) -0.09616(10) 0.23105(16) 0.0340(4) Uani 1 1 d . . . H7 H 0.2887 -0.0867 0.1482 0.041 Uiso 1 1 calc R . . C8 C 0.20759(19) -0.13410(9) 0.25723(14) 0.0266(3) Uani 1 1 d . . . C9 C 0.26193(19) -0.15128(9) 0.38127(13) 0.0254(3) Uani 1 1 d . . . C10 C -0.09938(19) -0.11325(9) 0.12496(13) 0.0249(3) Uani 1 1 d . . . C11 C -0.28699(19) -0.14108(9) 0.02702(14) 0.0288(3) Uani 1 1 d . . . C12 C -0.3993(3) -0.15163(13) 0.08857(19) 0.0479(5) Uani 1 1 d . . . H12A H -0.5203 -0.1706 0.0283 0.072 Uiso 1 1 calc R . . H12B H -0.4088 -0.1004 0.1219 0.072 Uiso 1 1 calc R . . H12C H -0.3406 -0.1906 0.1548 0.072 Uiso 1 1 calc R . . C13 C -0.2780(2) -0.21969(10) -0.02964(16) 0.0379(4) Uani 1 1 d . . . H13A H -0.2097 -0.2121 -0.0712 0.057 Uiso 1 1 calc R . . H13B H -0.4006 -0.2376 -0.0887 0.057 Uiso 1 1 calc R . . H13C H -0.2180 -0.2599 0.0346 0.057 Uiso 1 1 calc R . . C14 C -0.3784(2) -0.07784(11) -0.07350(16) 0.0413(4) Uani 1 1 d . . . H14A H -0.3096 -0.0712 -0.1149 0.062 Uiso 1 1 calc R . . H14B H -0.3824 -0.0270 -0.0370 0.062 Uiso 1 1 calc R . . H14C H -0.5016 -0.0949 -0.1328 0.062 Uiso 1 1 calc R . . C15 C -0.08175(18) -0.03048(9) 0.17594(14) 0.0268(3) Uani 1 1 d . . . C16 C -0.0942(2) -0.01937(10) 0.27748(16) 0.0342(4) Uani 1 1 d . . . H16 H -0.1136 -0.0631 0.3169 0.041 Uiso 1 1 calc R . . C17 C -0.0779(3) 0.05693(13) 0.32104(19) 0.0493(5) Uani 1 1 d . . . H17 H -0.0842 0.0659 0.3925 0.059 Uiso 1 1 calc R . . C18 C -0.0529(2) 0.12018(11) 0.26373(19) 0.0448(5) Uani 1 1 d . . . H18 H -0.0449 0.1730 0.2930 0.054 Uiso 1 1 calc R . . C19 C -0.0398(3) 0.10502(12) 0.1624(2) 0.0486(5) Uani 1 1 d . . . H19 H -0.0193 0.1483 0.1227 0.058 Uiso 1 1 calc R . . N1 N 0.14544(17) -0.19254(8) 0.40477(12) 0.0312(3) Uani 1 1 d . . . N2 N 0.03479(16) -0.16045(8) 0.16254(11) 0.0275(3) Uani 1 1 d . . . N3 N -0.0550(3) 0.02993(10) 0.11688(16) 0.0491(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0407(9) 0.0407(10) 0.0331(8) 0.0026(7) 0.0219(7) 0.0014(8) C2 0.0457(10) 0.0450(10) 0.0266(8) -0.0001(7) 0.0167(7) 0.0053(8) C3 0.0318(8) 0.0402(9) 0.0272(8) -0.0049(7) 0.0078(6) 0.0033(7) C4 0.0224(7) 0.0295(8) 0.0279(8) -0.0032(6) 0.0081(6) 0.0043(6) C5 0.0218(7) 0.0349(9) 0.0392(9) -0.0041(7) 0.0099(6) -0.0009(6) C6 0.0294(8) 0.0387(9) 0.0466(10) 0.0010(8) 0.0215(7) -0.0034(7) C7 0.0326(8) 0.0365(9) 0.0325(8) 0.0022(7) 0.0164(7) -0.0003(7) C8 0.0238(7) 0.0255(7) 0.0268(7) -0.0018(6) 0.0100(6) 0.0018(6) C9 0.0230(6) 0.0243(7) 0.0268(7) -0.0012(6) 0.0111(6) 0.0034(6) C10 0.0261(7) 0.0261(7) 0.0233(7) 0.0005(6) 0.0132(6) -0.0016(6) C11 0.0233(7) 0.0305(8) 0.0267(7) 0.0010(6) 0.0086(6) -0.0017(6) C12 0.0375(9) 0.0615(13) 0.0494(11) -0.0073(10) 0.0255(9) -0.0157(9) C13 0.0311(8) 0.0322(9) 0.0357(9) -0.0046(7) 0.0064(7) -0.0037(7) C14 0.0356(8) 0.0370(9) 0.0332(9) -0.0007(8) 0.0043(7) 0.0009(7) C15 0.0196(6) 0.0270(7) 0.0294(8) -0.0009(6) 0.0093(6) 0.0010(5) C16 0.0410(9) 0.0309(8) 0.0374(9) 0.0011(7) 0.0251(8) 0.0055(7) C17 0.0496(11) 0.0506(12) 0.0486(12) -0.0072(9) 0.0256(9) 0.0115(9) C18 0.0299(8) 0.0326(9) 0.0572(12) -0.0139(9) 0.0115(8) 0.0010(7) C19 0.0493(11) 0.0319(10) 0.0660(14) 0.0044(9) 0.0304(10) 0.0026(8) N1 0.0294(6) 0.0327(7) 0.0310(7) -0.0003(6) 0.0151(6) -0.0002(6) N2 0.0261(6) 0.0301(7) 0.0245(6) -0.0009(5) 0.0116(5) -0.0012(5) N3 0.0594(10) 0.0368(9) 0.0550(11) 0.0041(7) 0.0321(9) 0.0007(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.319(2) . ? C1 C2 1.401(2) . ? C1 H1 0.9500 . ? C2 C3 1.358(3) . ? C2 H2 0.9500 . ? C3 C4 1.414(2) . ? C3 H3 0.9500 . ? C4 C5 1.414(2) . ? C4 C9 1.420(2) . ? C5 C6 1.368(3) . ? C5 H5 0.9500 . ? C6 C7 1.412(2) . ? C6 H6 0.9500 . ? C7 C8 1.363(2) . ? C7 H7 0.9500 . ? C8 N2 1.4261(18) . ? C8 C9 1.429(2) . ? C9 N1 1.372(2) . ? C10 N2 1.2758(19) . ? C10 C15 1.507(2) . ? C10 C11 1.526(2) . ? C11 C13 1.524(2) . ? C11 C12 1.534(2) . ? C11 C14 1.535(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N3 1.350(2) . ? C15 C16 1.363(2) . ? C16 C17 1.374(3) . ? C16 H16 0.9500 . ? C17 C18 1.366(3) . ? C17 H17 0.9500 . ? C18 C19 1.375(3) . ? C18 H18 0.9500 . ? C19 N3 1.365(3) . ? C19 H19 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 124.32(17) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C3 C2 C1 119.13(16) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.68(15) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 123.05(14) . . ? C5 C4 C9 119.88(14) . . ? C3 C4 C9 117.07(15) . . ? C6 C5 C4 120.00(14) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.39(15) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 121.22(16) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 N2 121.22(14) . . ? C7 C8 C9 119.78(14) . . ? N2 C8 C9 118.94(13) . . ? N1 C9 C4 122.72(14) . . ? N1 C9 C8 118.62(13) . . ? C4 C9 C8 118.66(14) . . ? N2 C10 C15 122.50(13) . . ? N2 C10 C11 119.72(14) . . ? C15 C10 C11 117.76(12) . . ? C13 C11 C10 111.30(13) . . ? C13 C11 C12 109.83(15) . . ? C10 C11 C12 107.40(13) . . ? C13 C11 C14 109.40(14) . . ? C10 C11 C14 110.42(13) . . ? C12 C11 C14 108.44(15) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 C16 122.93(15) . . ? N3 C15 C10 117.42(14) . . ? C16 C15 C10 119.65(14) . . ? C15 C16 C17 117.96(17) . . ? C15 C16 H16 121.0 . . ? C17 C16 H16 121.0 . . ? C18 C17 C16 121.34(19) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 117.92(18) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? N3 C19 C18 122.18(19) . . ? N3 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C1 N1 C9 117.06(14) . . ? C10 N2 C8 118.69(13) . . ? C15 N3 C19 117.64(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.7(3) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 -178.58(16) . . . . ? C2 C3 C4 C9 1.6(2) . . . . ? C3 C4 C5 C6 179.52(16) . . . . ? C9 C4 C5 C6 -0.6(2) . . . . ? C4 C5 C6 C7 1.5(3) . . . . ? C5 C6 C7 C8 0.1(3) . . . . ? C6 C7 C8 N2 -179.52(15) . . . . ? C6 C7 C8 C9 -2.4(2) . . . . ? C5 C4 C9 N1 178.76(14) . . . . ? C3 C4 C9 N1 -1.4(2) . . . . ? C5 C4 C9 C8 -1.6(2) . . . . ? C3 C4 C9 C8 178.20(14) . . . . ? C7 C8 C9 N1 -177.22(14) . . . . ? N2 C8 C9 N1 -0.1(2) . . . . ? C7 C8 C9 C4 3.2(2) . . . . ? N2 C8 C9 C4 -179.68(13) . . . . ? N2 C10 C11 C13 -10.8(2) . . . . ? C15 C10 C11 C13 170.68(13) . . . . ? N2 C10 C11 C12 109.40(17) . . . . ? C15 C10 C11 C12 -69.08(18) . . . . ? N2 C10 C11 C14 -132.54(16) . . . . ? C15 C10 C11 C14 48.98(19) . . . . ? N2 C10 C15 N3 93.70(19) . . . . ? C11 C10 C15 N3 -87.86(18) . . . . ? N2 C10 C15 C16 -86.71(19) . . . . ? C11 C10 C15 C16 91.73(18) . . . . ? N3 C15 C16 C17 -0.3(3) . . . . ? C10 C15 C16 C17 -179.83(15) . . . . ? C15 C16 C17 C18 1.0(3) . . . . ? C16 C17 C18 C19 -1.7(3) . . . . ? C17 C18 C19 N3 1.5(3) . . . . ? C2 C1 N1 C9 0.9(3) . . . . ? C4 C9 N1 C1 0.2(2) . . . . ? C8 C9 N1 C1 -179.41(14) . . . . ? C15 C10 N2 C8 0.6(2) . . . . ? C11 C10 N2 C8 -177.77(13) . . . . ? C7 C8 N2 C10 -90.58(18) . . . . ? C9 C8 N2 C10 92.30(18) . . . . ? C16 C15 N3 C19 0.2(3) . . . . ? C10 C15 N3 C19 179.73(16) . . . . ? C18 C19 N3 C15 -0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.392 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.053 #===END data_Ligand4 _database_code_depnum_ccdc_archive 'CCDC 701154' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 N4' _chemical_formula_sum 'C25 H22 N4' _chemical_formula_weight 378.47 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.417(5) _cell_length_b 13.252(2) _cell_length_c 10.0650(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.944(8) _cell_angle_gamma 90.00 _cell_volume 3954.0(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8713 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6364 _diffrn_reflns_av_R_equivalents 0.1225 _diffrn_reflns_av_sigmaI/netI 0.2289 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3675 _reflns_number_gt 1171 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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^)+(0.0200P)^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 3675 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2603 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.94084(12) 0.4774(3) 0.4839(4) 0.0509(11) Uani 1 1 d . . . H1 H 0.9543 0.5367 0.4634 0.061 Uiso 1 1 calc R . . C2 C 0.94435(12) 0.4525(3) 0.6213(4) 0.0574(12) Uani 1 1 d . . . H2 H 0.9598 0.4951 0.6895 0.069 Uiso 1 1 calc R . . C3 C 0.92527(12) 0.3662(3) 0.6549(3) 0.0570(12) Uani 1 1 d . . . H3 H 0.9280 0.3485 0.7458 0.068 Uiso 1 1 calc R . . C4 C 0.90116(11) 0.3037(3) 0.5497(3) 0.0404(10) Uani 1 1 d . . . C5 C 0.87866(11) 0.2141(3) 0.5722(3) 0.0501(11) Uani 1 1 d . . . H5 H 0.8800 0.1921 0.6608 0.060 Uiso 1 1 calc R . . C6 C 0.85474(11) 0.1592(3) 0.4640(3) 0.0427(10) Uani 1 1 d . . . H6 H 0.8397 0.1011 0.4805 0.051 Uiso 1 1 calc R . . C7 C 0.85264(11) 0.1896(3) 0.3280(3) 0.0361(9) Uani 1 1 d . . . C8 C 0.82725(11) 0.1334(3) 0.2098(3) 0.0377(10) Uani 1 1 d . . . C9 C 0.83230(10) 0.1581(3) 0.0856(3) 0.0407(10) Uani 1 1 d . . . H9 H 0.8157 0.1219 0.0122 0.049 Uiso 1 1 calc R . . C10 C 0.86280(11) 0.2401(3) 0.0550(3) 0.0391(10) Uani 1 1 d . . . C11 C 0.87591(11) 0.2749(3) 0.3041(3) 0.0344(9) Uani 1 1 d . . . C12 C 0.89951(11) 0.3353(3) 0.4141(3) 0.0372(9) Uani 1 1 d . . . C13 C 0.83788(11) 0.3030(2) -0.0679(3) 0.0512(11) Uani 1 1 d . . . H13A H 0.8096 0.3259 -0.0517 0.077 Uiso 1 1 calc R . . H13B H 0.8325 0.2620 -0.1486 0.077 Uiso 1 1 calc R . . H13C H 0.8560 0.3600 -0.0799 0.077 Uiso 1 1 calc R . . C14 C 0.90580(12) 0.1995(3) 0.0192(3) 0.0393(10) Uani 1 1 d . . . C15 C 0.90468(12) 0.1151(3) -0.0630(3) 0.0452(10) Uani 1 1 d . . . H15 H 0.8780 0.0786 -0.0893 0.054 Uiso 1 1 calc R . . C16 C 0.94225(14) 0.0846(3) -0.1061(3) 0.0493(10) Uani 1 1 d . . . C17 C 0.98096(13) 0.1401(3) -0.0612(4) 0.0638(12) Uani 1 1 d . . . H17 H 1.0075 0.1225 -0.0869 0.077 Uiso 1 1 calc R . . C18 C 0.97997(13) 0.2224(3) 0.0225(4) 0.0717(13) Uani 1 1 d . . . H18 H 1.0065 0.2585 0.0531 0.086 Uiso 1 1 calc R . . C19 C 0.94047(12) -0.0044(3) -0.2023(3) 0.0693(13) Uani 1 1 d . . . H19A H 0.9240 -0.0587 -0.1731 0.104 Uiso 1 1 calc R . . H19B H 0.9706 -0.0265 -0.2015 0.104 Uiso 1 1 calc R . . H19C H 0.9257 0.0156 -0.2930 0.104 Uiso 1 1 calc R . . C20 C 0.79419(12) 0.0554(3) 0.2283(3) 0.0394(10) Uani 1 1 d . . . C21 C 0.76003(12) 0.0782(3) 0.2946(3) 0.0437(10) Uani 1 1 d . . . H21 H 0.7588 0.1422 0.3314 0.052 Uiso 1 1 calc R . . C22 C 0.72783(12) 0.0072(3) 0.3067(3) 0.0431(10) Uani 1 1 d . . . C23 C 0.73177(12) -0.0866(3) 0.2517(3) 0.0523(11) Uani 1 1 d . . . H23 H 0.7111 -0.1374 0.2571 0.063 Uiso 1 1 calc R . . C24 C 0.76677(13) -0.1039(3) 0.1885(3) 0.0555(11) Uani 1 1 d . . . H24 H 0.7690 -0.1680 0.1530 0.067 Uiso 1 1 calc R . . C25 C 0.68982(11) 0.0338(3) 0.3740(3) 0.0610(12) Uani 1 1 d . . . H25A H 0.6618 0.0110 0.3180 0.092 Uiso 1 1 calc R . . H25B H 0.6888 0.1056 0.3853 0.092 Uiso 1 1 calc R . . H25C H 0.6947 0.0016 0.4616 0.092 Uiso 1 1 calc R . . N1 N 0.91930(9) 0.4208(2) 0.3826(3) 0.0455(8) Uani 1 1 d . . . N2 N 0.87307(9) 0.3074(2) 0.1724(3) 0.0396(8) Uani 1 1 d . . . N3 N 0.94300(12) 0.2531(2) 0.0622(3) 0.0563(9) Uani 1 1 d . . . N4 N 0.79781(10) -0.0357(3) 0.1743(3) 0.0491(9) Uani 1 1 d . . . H2N H 0.8921(10) 0.357(2) 0.171(3) 0.059 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.043(3) 0.047(3) 0.065(3) -0.006(2) 0.015(2) -0.005(2) C2 0.050(3) 0.069(4) 0.049(3) -0.009(2) 0.003(2) 0.002(3) C3 0.057(3) 0.075(4) 0.038(2) -0.002(2) 0.009(2) 0.002(3) C4 0.034(2) 0.055(3) 0.033(2) -0.002(2) 0.0073(18) 0.007(2) C5 0.054(3) 0.058(3) 0.039(2) 0.009(2) 0.012(2) 0.001(2) C6 0.044(2) 0.037(3) 0.048(2) 0.003(2) 0.011(2) 0.000(2) C7 0.039(2) 0.042(3) 0.030(2) 0.002(2) 0.0132(19) 0.003(2) C8 0.035(2) 0.038(3) 0.044(2) 0.002(2) 0.0168(19) 0.000(2) C9 0.035(2) 0.045(3) 0.041(2) -0.004(2) 0.0068(19) -0.006(2) C10 0.043(3) 0.040(3) 0.032(2) -0.003(2) 0.0034(19) -0.008(2) C11 0.036(2) 0.039(3) 0.029(2) 0.005(2) 0.0092(18) 0.004(2) C12 0.037(2) 0.037(3) 0.038(2) -0.003(2) 0.0079(19) 0.000(2) C13 0.059(3) 0.059(3) 0.032(2) 0.001(2) 0.0021(18) 0.007(2) C14 0.042(3) 0.039(3) 0.039(2) 0.006(2) 0.013(2) 0.000(2) C15 0.038(3) 0.052(3) 0.048(2) 0.000(2) 0.014(2) -0.005(2) C16 0.050(3) 0.042(3) 0.060(2) 0.002(2) 0.020(2) -0.008(3) C17 0.048(3) 0.063(4) 0.090(3) -0.010(3) 0.035(3) -0.005(3) C18 0.039(3) 0.069(4) 0.109(4) -0.017(3) 0.020(3) -0.017(3) C19 0.067(3) 0.063(3) 0.086(3) -0.014(2) 0.034(2) -0.002(3) C20 0.043(3) 0.040(3) 0.035(2) 0.002(2) 0.0099(19) -0.004(2) C21 0.045(3) 0.043(3) 0.044(2) -0.0026(19) 0.012(2) -0.002(2) C22 0.035(3) 0.054(3) 0.039(2) 0.006(2) 0.0051(19) 0.000(2) C23 0.050(3) 0.049(3) 0.058(3) 0.001(2) 0.012(2) -0.013(2) C24 0.059(3) 0.038(3) 0.067(3) -0.006(2) 0.010(2) -0.004(3) C25 0.052(3) 0.068(3) 0.066(3) 0.006(2) 0.021(2) -0.004(2) N1 0.043(2) 0.043(2) 0.0486(19) -0.0052(18) 0.0060(16) -0.0018(18) N2 0.049(2) 0.036(2) 0.0346(18) -0.0016(18) 0.0092(15) -0.0096(16) N3 0.038(2) 0.051(2) 0.082(2) -0.0092(18) 0.0169(19) -0.012(2) N4 0.053(2) 0.040(2) 0.056(2) -0.0082(18) 0.0138(17) -0.010(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 C1 N1 1.316(4) . ? C1 C2 1.403(4) . ? C1 H1 0.9300 . ? C2 C3 1.360(5) . ? C2 H2 0.9300 . ? C3 C4 1.413(4) . ? C3 H3 0.9300 . ? C4 C12 1.418(4) . ? C4 C5 1.414(4) . ? C5 C6 1.375(4) . ? C5 H5 0.9300 . ? C6 C7 1.414(4) . ? C6 H6 0.9300 . ? C7 C11 1.382(4) . ? C7 C8 1.468(4) . ? C8 C9 1.334(4) . ? C8 C20 1.482(4) . ? C9 C10 1.505(4) . ? C9 H9 0.9300 . ? C10 N2 1.458(4) . ? C10 C14 1.530(4) . ? C10 C13 1.542(4) . ? C11 N2 1.378(4) . ? C11 C12 1.423(4) . ? C12 N1 1.354(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N3 1.325(4) . ? C14 C15 1.386(4) . ? C15 C16 1.371(4) . ? C15 H15 0.9300 . ? C16 C17 1.376(4) . ? C16 C19 1.519(4) . ? C17 C18 1.383(5) . ? C17 H17 0.9300 . ? C18 N3 1.338(4) . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N4 1.340(4) . ? C20 C21 1.388(4) . ? C21 C22 1.383(4) . ? C21 H21 0.9300 . ? C22 C23 1.377(4) . ? C22 C25 1.506(4) . ? C23 C24 1.376(4) . ? C23 H23 0.9300 . ? C24 N4 1.338(4) . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? N2 H2N 0.88(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 N1 C1 C2 123.0(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 120.1(4) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.1(4) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C12 116.7(4) . . ? C3 C4 C5 124.1(4) . . ? C12 C4 C5 119.2(3) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 121.2(3) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C11 C7 C6 119.1(3) . . ? C11 C7 C8 118.1(3) . . ? C6 C7 C8 122.7(3) . . ? C9 C8 C7 119.0(3) . . ? C9 C8 C20 120.9(3) . . ? C7 C8 C20 120.0(3) . . ? C8 C9 C10 125.1(3) . . ? C8 C9 H9 117.4 . . ? C10 C9 H9 117.4 . . ? N2 C10 C9 107.8(3) . . ? N2 C10 C14 111.5(3) . . ? C9 C10 C14 113.1(3) . . ? N2 C10 C13 107.3(3) . . ? C9 C10 C13 109.9(3) . . ? C14 C10 C13 107.1(3) . . ? N2 C11 C7 119.9(3) . . ? N2 C11 C12 118.9(3) . . ? C7 C11 C12 120.9(3) . . ? N1 C12 C4 123.4(3) . . ? N1 C12 C11 117.5(3) . . ? C4 C12 C11 119.0(4) . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 122.2(3) . . ? N3 C14 C10 116.5(3) . . ? C15 C14 C10 121.1(3) . . ? C16 C15 C14 121.0(4) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 116.8(4) . . ? C15 C16 C19 121.2(4) . . ? C17 C16 C19 122.0(4) . . ? C16 C17 C18 119.2(4) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? N3 C18 C17 123.8(4) . . ? N3 C18 H18 118.1 . . ? C17 C18 H18 118.1 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 C21 122.0(3) . . ? N4 C20 C8 117.2(3) . . ? C21 C20 C8 120.8(4) . . ? C22 C21 C20 121.1(4) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C23 C22 C21 116.8(4) . . ? C23 C22 C25 122.4(4) . . ? C21 C22 C25 120.7(4) . . ? C24 C23 C22 118.8(4) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? N4 C24 C23 125.1(4) . . ? N4 C24 H24 117.5 . . ? C23 C24 H24 117.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C1 N1 C12 117.8(3) . . ? C11 N2 C10 123.0(3) . . ? C11 N2 H2N 110(2) . . ? C10 N2 H2N 118(2) . . ? C14 N3 C18 116.9(3) . . ? C24 N4 C20 116.2(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.198 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.053 #===END data_Ligand6 _database_code_depnum_ccdc_archive 'CCDC 701155' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H16 Br2 N4' _chemical_formula_sum 'C23 H16 Br2 N4' _chemical_formula_weight 508.22 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5388(7) _cell_length_b 19.5573(8) _cell_length_c 10.6246(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.491(2) _cell_angle_gamma 90.00 _cell_volume 2023.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 15058 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 4.024 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7478 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0709 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4387 _reflns_number_gt 2917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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^)+(0.0444P)^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 4387 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 C1 C 0.7177(4) 0.97314(15) 0.7307(3) 0.0286(8) Uani 1 1 d . . . H1 H 0.8085 0.9862 0.7777 0.034 Uiso 1 1 calc R . . C2 C 0.6141(4) 1.01100(16) 0.7522(4) 0.0305(8) Uani 1 1 d . . . H2 H 0.6366 1.0481 0.8114 0.037 Uiso 1 1 calc R . . C3 C 0.4811(4) 0.99252(15) 0.6853(4) 0.0281(8) Uani 1 1 d . . . H3 H 0.4114 1.0172 0.6980 0.034 Uiso 1 1 calc R . . C4 C 0.4483(3) 0.93556(15) 0.5959(3) 0.0234(7) Uani 1 1 d . . . C5 C 0.3126(3) 0.91355(16) 0.5207(3) 0.0286(8) Uani 1 1 d . . . H5 H 0.2390 0.9365 0.5291 0.034 Uiso 1 1 calc R . . C6 C 0.2897(3) 0.85842(15) 0.4356(4) 0.0283(8) Uani 1 1 d . . . H6 H 0.2000 0.8441 0.3870 0.034 Uiso 1 1 calc R . . C7 C 0.3995(3) 0.82282(15) 0.4199(3) 0.0240(7) Uani 1 1 d . . . C8 C 0.3794(3) 0.76243(14) 0.3310(3) 0.0226(7) Uani 1 1 d . . . C9 C 0.4808(3) 0.74152(15) 0.2955(3) 0.0269(8) Uani 1 1 d . . . H9 H 0.4659 0.7041 0.2375 0.032 Uiso 1 1 calc R . . C10 C 0.6201(3) 0.77621(14) 0.3457(3) 0.0237(7) Uani 1 1 d . . . C11 C 0.5334(3) 0.84452(14) 0.4902(3) 0.0213(7) Uani 1 1 d . . . C12 C 0.5604(3) 0.90140(14) 0.5807(3) 0.0204(7) Uani 1 1 d . . . C13 C 0.7345(3) 0.72230(15) 0.3709(4) 0.0313(8) Uani 1 1 d . . . H13A H 0.8226 0.7442 0.4085 0.047 Uiso 1 1 calc R . . H13B H 0.7240 0.7008 0.2862 0.047 Uiso 1 1 calc R . . H13C H 0.7281 0.6884 0.4335 0.047 Uiso 1 1 calc R . . C14 C 0.6329(3) 0.82993(15) 0.2469(3) 0.0262(7) Uani 1 1 d . . . C15 C 0.5315(3) 0.84479(16) 0.1214(3) 0.0307(8) Uani 1 1 d . . . H15 H 0.4483 0.8214 0.0918 0.037 Uiso 1 1 calc R . . C16 C 0.5546(4) 0.89470(17) 0.0401(4) 0.0374(9) Uani 1 1 d . . . H16 H 0.4874 0.9049 -0.0447 0.045 Uiso 1 1 calc R . . C17 C 0.6782(4) 0.92925(17) 0.0861(4) 0.0360(9) Uani 1 1 d . . . H17 H 0.6970 0.9632 0.0343 0.043 Uiso 1 1 calc R . . C18 C 0.7729(3) 0.91074(16) 0.2130(4) 0.0310(8) Uani 1 1 d . . . C19 C 0.2483(3) 0.72335(14) 0.2880(3) 0.0241(7) Uani 1 1 d . . . C20 C 0.1662(3) 0.71305(15) 0.1515(4) 0.0270(8) Uani 1 1 d . . . H20 H 0.1897 0.7325 0.0835 0.032 Uiso 1 1 calc R . . C21 C 0.0488(3) 0.67329(15) 0.1181(4) 0.0317(8) Uani 1 1 d . . . H21 H -0.0075 0.6661 0.0273 0.038 Uiso 1 1 calc R . . C22 C 0.0163(3) 0.64458(15) 0.2203(4) 0.0305(8) Uani 1 1 d . . . H22 H -0.0615 0.6176 0.2013 0.037 Uiso 1 1 calc R . . C23 C 0.1044(3) 0.65775(15) 0.3516(3) 0.0272(8) Uani 1 1 d . . . N1 N 0.6939(3) 0.92036(12) 0.6480(3) 0.0244(6) Uani 1 1 d . . . N2 N 0.6409(3) 0.80885(13) 0.4765(3) 0.0233(6) Uani 1 1 d . . . N3 N 0.7543(3) 0.86345(12) 0.2917(3) 0.0264(6) Uani 1 1 d . . . N4 N 0.2167(3) 0.69558(12) 0.3894(3) 0.0258(6) Uani 1 1 d . . . Br1 Br 0.94526(4) 0.95697(2) 0.28382(5) 0.05566(16) Uani 1 1 d . . . Br2 Br 0.06676(4) 0.616349(18) 0.49770(4) 0.04048(13) Uani 1 1 d . . . H1N H 0.711(3) 0.8271(15) 0.511(3) 0.020(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0278(19) 0.0246(16) 0.028(2) 0.0002(15) 0.0043(16) -0.0041(14) C2 0.039(2) 0.0248(16) 0.028(2) -0.0057(15) 0.0122(17) 0.0005(15) C3 0.034(2) 0.0246(16) 0.029(2) 0.0004(15) 0.0147(17) 0.0045(15) C4 0.0248(18) 0.0232(15) 0.0214(18) 0.0026(14) 0.0078(15) 0.0008(14) C5 0.0217(18) 0.0288(17) 0.035(2) 0.0031(16) 0.0104(16) 0.0063(14) C6 0.0198(18) 0.0296(17) 0.033(2) 0.0031(16) 0.0066(16) -0.0051(14) C7 0.0214(18) 0.0251(16) 0.0237(19) 0.0037(14) 0.0068(15) 0.0004(13) C8 0.0218(17) 0.0230(15) 0.0198(18) 0.0019(14) 0.0043(14) -0.0024(13) C9 0.0245(18) 0.0257(16) 0.029(2) -0.0068(15) 0.0084(16) -0.0059(14) C10 0.0202(17) 0.0267(16) 0.0222(19) -0.0053(14) 0.0056(15) -0.0031(13) C11 0.0206(17) 0.0204(16) 0.0211(18) 0.0031(13) 0.0061(15) 0.0001(12) C12 0.0210(17) 0.0183(15) 0.0186(17) 0.0058(13) 0.0039(14) 0.0007(13) C13 0.0277(19) 0.0264(16) 0.040(2) -0.0035(16) 0.0139(17) 0.0014(14) C14 0.0264(19) 0.0254(16) 0.026(2) -0.0068(15) 0.0096(16) 0.0016(14) C15 0.027(2) 0.0329(17) 0.028(2) -0.0060(16) 0.0059(16) -0.0019(15) C16 0.041(2) 0.039(2) 0.027(2) 0.0018(17) 0.0070(18) 0.0068(17) C17 0.046(2) 0.0328(18) 0.035(2) 0.0098(17) 0.021(2) 0.0062(17) C18 0.027(2) 0.0344(18) 0.032(2) -0.0005(17) 0.0117(17) -0.0005(15) C19 0.0232(18) 0.0233(15) 0.0256(19) -0.0017(14) 0.0090(15) 0.0014(13) C20 0.0208(18) 0.0303(17) 0.027(2) -0.0009(15) 0.0064(15) -0.0005(14) C21 0.027(2) 0.0320(17) 0.025(2) -0.0029(16) -0.0029(16) 0.0002(15) C22 0.0197(18) 0.0256(16) 0.037(2) -0.0020(16) 0.0010(17) -0.0050(14) C23 0.0248(19) 0.0241(16) 0.032(2) 0.0032(15) 0.0101(16) -0.0005(14) N1 0.0237(16) 0.0247(14) 0.0222(15) 0.0002(12) 0.0057(13) 0.0001(11) N2 0.0168(15) 0.0257(14) 0.0242(16) -0.0059(12) 0.0045(13) -0.0012(12) N3 0.0203(15) 0.0265(13) 0.0311(17) -0.0011(13) 0.0085(13) -0.0017(12) N4 0.0219(15) 0.0261(13) 0.0270(17) -0.0009(12) 0.0068(13) -0.0020(11) Br1 0.0382(3) 0.0560(3) 0.0679(3) 0.0154(2) 0.0150(2) -0.01628(19) Br2 0.0360(2) 0.0442(2) 0.0416(2) 0.00987(18) 0.01524(19) -0.00630(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.316(4) . ? C1 C2 1.408(4) . ? C1 H1 0.9300 . ? C2 C3 1.356(5) . ? C2 H2 0.9300 . ? C3 C4 1.418(4) . ? C3 H3 0.9300 . ? C4 C5 1.412(4) . ? C4 C12 1.418(4) . ? C5 C6 1.368(4) . ? C5 H5 0.9300 . ? C6 C7 1.414(4) . ? C6 H6 0.9300 . ? C7 C11 1.387(4) . ? C7 C8 1.476(4) . ? C8 C9 1.326(4) . ? C8 C19 1.490(4) . ? C9 C10 1.517(4) . ? C9 H9 0.9300 . ? C10 N2 1.467(4) . ? C10 C14 1.527(4) . ? C10 C13 1.546(4) . ? C11 N2 1.385(4) . ? C11 C12 1.426(4) . ? C12 N1 1.364(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N3 1.352(4) . ? C14 C15 1.384(4) . ? C15 C16 1.385(5) . ? C15 H15 0.9300 . ? C16 C17 1.380(5) . ? C16 H16 0.9300 . ? C17 C18 1.384(5) . ? C17 H17 0.9300 . ? C18 N3 1.311(4) . ? C18 Br1 1.907(3) . ? C19 N4 1.356(4) . ? C19 C20 1.391(5) . ? C20 C21 1.388(4) . ? C20 H20 0.9300 . ? C21 C22 1.377(5) . ? C21 H21 0.9300 . ? C22 C23 1.373(4) . ? C22 H22 0.9300 . ? C23 N4 1.321(4) . ? C23 Br2 1.921(3) . ? N2 H1N 0.77(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 N1 C1 C2 124.0(3) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 123.5(3) . . ? C5 C4 C12 119.9(3) . . ? C3 C4 C12 116.5(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 121.4(3) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C11 C7 C6 119.8(3) . . ? C11 C7 C8 117.2(3) . . ? C6 C7 C8 123.1(3) . . ? C9 C8 C7 119.7(3) . . ? C9 C8 C19 120.6(3) . . ? C7 C8 C19 119.7(3) . . ? C8 C9 C10 122.6(3) . . ? C8 C9 H9 118.7 . . ? C10 C9 H9 118.7 . . ? N2 C10 C9 107.6(3) . . ? N2 C10 C14 109.3(2) . . ? C9 C10 C14 113.2(3) . . ? N2 C10 C13 108.0(3) . . ? C9 C10 C13 110.0(2) . . ? C14 C10 C13 108.6(3) . . ? N2 C11 C7 119.6(3) . . ? N2 C11 C12 120.3(3) . . ? C7 C11 C12 120.0(3) . . ? N1 C12 C4 123.3(3) . . ? N1 C12 C11 117.7(3) . . ? C4 C12 C11 119.0(3) . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 121.0(3) . . ? N3 C14 C10 114.3(3) . . ? C15 C14 C10 124.6(3) . . ? C14 C15 C16 119.6(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 119.5(3) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 116.6(3) . . ? C16 C17 H17 121.7 . . ? C18 C17 H17 121.7 . . ? N3 C18 C17 125.3(3) . . ? N3 C18 Br1 115.8(3) . . ? C17 C18 Br1 118.9(3) . . ? N4 C19 C20 121.8(3) . . ? N4 C19 C8 116.3(3) . . ? C20 C19 C8 121.8(3) . . ? C21 C20 C19 119.1(3) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C22 C21 C20 119.6(3) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C23 C22 C21 116.7(3) . . ? C23 C22 H22 121.7 . . ? C21 C22 H22 121.7 . . ? N4 C23 C22 126.4(3) . . ? N4 C23 Br2 115.4(2) . . ? C22 C23 Br2 118.3(2) . . ? C1 N1 C12 117.3(3) . . ? C11 N2 C10 119.1(3) . . ? C11 N2 H1N 113(2) . . ? C10 N2 H1N 115(3) . . ? C18 N3 C14 118.0(3) . . ? C23 N4 C19 116.5(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.631 _refine_diff_density_min -0.758 _refine_diff_density_rms 0.087 #===END data_Complex9 _database_code_depnum_ccdc_archive 'CCDC 701156' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H26 Cl2 N4 Pd, 2(C H2 Cl2)' _chemical_formula_sum 'C37 H30 Cl6 N4 Pd' _chemical_formula_weight 849.75 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' Cl Cl 0.1484 0.1585 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9448(4) _cell_length_b 12.9038(6) _cell_length_c 13.8457(6) _cell_angle_alpha 80.351(2) _cell_angle_beta 86.891(2) _cell_angle_gamma 67.035(2) _cell_volume 1774.84(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 24737 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.009 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.73984 _exptl_absorpt_correction_T_max 0.87358 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _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 23285 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0707 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 29.99 _reflns_number_total 10318 _reflns_number_gt 7839 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0493P)^2^+7.1641P] 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 10318 _refine_ls_number_parameters 438 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1008 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.1589 _refine_ls_wR_factor_gt 0.1460 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7103(5) 0.4911(4) -0.1218(3) 0.0347(10) Uani 1 1 d . . . H1 H 0.6331 0.5451 -0.1565 0.042 Uiso 1 1 calc R . . C2 C 0.8292(5) 0.5085(5) -0.1349(4) 0.0412(12) Uani 1 1 d . . . H2 H 0.8313 0.5735 -0.1776 0.049 Uiso 1 1 calc R . . C3 C 0.9422(5) 0.4321(4) -0.0863(4) 0.0351(10) Uani 1 1 d . . . H3 H 1.0232 0.4431 -0.0958 0.042 Uiso 1 1 calc R . . C4 C 0.9371(4) 0.3363(4) -0.0218(3) 0.0284(9) Uani 1 1 d . . . C5 C 1.0485(4) 0.2510(4) 0.0292(4) 0.0332(10) Uani 1 1 d . . . H5 H 1.1323 0.2572 0.0229 0.040 Uiso 1 1 calc R . . C6 C 1.0363(4) 0.1592(4) 0.0878(3) 0.0300(9) Uani 1 1 d . . . H6 H 1.1128 0.1012 0.1202 0.036 Uiso 1 1 calc R . . C7 C 0.9116(4) 0.1485(4) 0.1013(3) 0.0253(8) Uani 1 1 d . . . C8 C 0.8972(4) 0.0490(4) 0.1618(3) 0.0276(9) Uani 1 1 d . . . C9 C 0.7836(4) 0.0348(4) 0.1553(3) 0.0312(9) Uani 1 1 d . . . H9 H 0.7763 -0.0313 0.1927 0.037 Uiso 1 1 calc R . . C10 C 0.6654(4) 0.1170(4) 0.0921(3) 0.0291(9) Uani 1 1 d . . . C11 C 0.8015(4) 0.2330(4) 0.0536(3) 0.0236(8) Uani 1 1 d . . . C12 C 0.8124(4) 0.3254(4) -0.0105(3) 0.0246(8) Uani 1 1 d . . . C13 C 0.6698(5) 0.0714(4) -0.0035(4) 0.0366(10) Uani 1 1 d . . . H13A H 0.5864 0.1155 -0.0400 0.055 Uiso 1 1 calc R . . H13B H 0.6818 -0.0089 0.0111 0.055 Uiso 1 1 calc R . . H13C H 0.7440 0.0785 -0.0430 0.055 Uiso 1 1 calc R . . C14 C 0.5429(4) 0.1263(4) 0.1548(3) 0.0343(10) Uani 1 1 d . . . C15 C 0.4849(5) 0.0471(5) 0.1571(4) 0.0452(13) Uani 1 1 d . . . H15 H 0.5159 -0.0112 0.1174 0.054 Uiso 1 1 calc R . . C16 C 0.3795(5) 0.0574(6) 0.2205(4) 0.0530(16) Uani 1 1 d . . . H16 H 0.3353 0.0066 0.2233 0.064 Uiso 1 1 calc R . . C17 C 0.3388(5) 0.1403(6) 0.2789(4) 0.0521(16) Uani 1 1 d . . . H17 H 0.2662 0.1476 0.3218 0.063 Uiso 1 1 calc R . . C18 C 0.4052(4) 0.2141(5) 0.2748(4) 0.0407(12) Uani 1 1 d . . . C19 C 0.3711(5) 0.3025(5) 0.3389(4) 0.0494(15) Uani 1 1 d . . . C20 C 0.2566(7) 0.3308(8) 0.3956(6) 0.079(2) Uani 1 1 d . . . H20 H 0.1993 0.2915 0.3946 0.095 Uiso 1 1 calc R . . C21 C 0.2256(9) 0.4154(9) 0.4533(6) 0.101(3) Uani 1 1 d . . . H21 H 0.1466 0.4337 0.4906 0.121 Uiso 1 1 calc R . . C22 C 0.3054(10) 0.4722(7) 0.4575(6) 0.094(3) Uani 1 1 d . . . H22 H 0.2831 0.5301 0.4973 0.113 Uiso 1 1 calc R . . C23 C 0.4188(9) 0.4447(7) 0.4036(6) 0.082(2) Uani 1 1 d . . . H23 H 0.4761 0.4838 0.4060 0.098 Uiso 1 1 calc R . . C24 C 0.4510(7) 0.3600(6) 0.3452(5) 0.0621(18) Uani 1 1 d . . . H24 H 0.5308 0.3417 0.3089 0.075 Uiso 1 1 calc R . . C25 C 1.0089(4) -0.0384(4) 0.2241(3) 0.0276(9) Uani 1 1 d . . . C26 C 1.0573(5) -0.1521(4) 0.2115(4) 0.0367(10) Uani 1 1 d . . . H26 H 1.0223 -0.1752 0.1615 0.044 Uiso 1 1 calc R . . C27 C 1.1571(5) -0.2306(4) 0.2733(4) 0.0431(12) Uani 1 1 d . . . H27 H 1.1927 -0.3088 0.2661 0.052 Uiso 1 1 calc R . . C28 C 1.2048(5) -0.1941(4) 0.3458(4) 0.0383(11) Uani 1 1 d . . . H28 H 1.2726 -0.2471 0.3898 0.046 Uiso 1 1 calc R . . C29 C 1.1525(4) -0.0789(4) 0.3536(3) 0.0277(9) Uani 1 1 d . . . C30 C 1.1984(4) -0.0343(4) 0.4312(3) 0.0288(9) Uani 1 1 d . . . C31 C 1.3288(5) -0.0870(4) 0.4680(4) 0.0363(10) Uani 1 1 d . . . H31 H 1.3890 -0.1535 0.4448 0.044 Uiso 1 1 calc R . . C32 C 1.3701(5) -0.0425(5) 0.5381(4) 0.0451(13) Uani 1 1 d . . . H32 H 1.4589 -0.0784 0.5623 0.054 Uiso 1 1 calc R . . C33 C 1.2833(6) 0.0537(5) 0.5731(4) 0.0472(14) Uani 1 1 d . . . H33 H 1.3126 0.0840 0.6210 0.057 Uiso 1 1 calc R . . C34 C 1.1538(6) 0.1057(5) 0.5384(4) 0.0420(12) Uani 1 1 d . . . H34 H 1.0936 0.1713 0.5630 0.050 Uiso 1 1 calc R . . C35 C 1.1119(4) 0.0621(4) 0.4678(3) 0.0323(10) Uani 1 1 d . . . H35 H 1.0229 0.0983 0.4440 0.039 Uiso 1 1 calc R . . C36 C 0.7070(6) -0.3441(5) 0.2682(5) 0.0519(14) Uani 1 1 d . . . H36A H 0.7076 -0.3699 0.2047 0.062 Uiso 1 1 calc R . . H36B H 0.7259 -0.4109 0.3206 0.062 Uiso 1 1 calc R . . C37 C 0.8790(6) 0.2934(5) 0.2858(4) 0.0523(15) Uani 1 1 d D . . H37A H 0.8328 0.3290 0.2219 0.063 Uiso 1 1 calc R A 1 H37B H 0.9540 0.2222 0.2758 0.063 Uiso 1 1 calc R A 1 N1 N 0.7019(3) 0.4019(3) -0.0627(3) 0.0257(7) Uani 1 1 d . . . N2 N 0.6680(3) 0.2338(3) 0.0689(3) 0.0240(7) Uani 1 1 d . . . N3 N 0.5063(4) 0.2055(3) 0.2124(3) 0.0327(8) Uani 1 1 d . . . N4 N 1.0564(3) -0.0012(3) 0.2924(3) 0.0257(7) Uani 1 1 d . . . Cl1 Cl 0.41472(11) 0.50604(10) -0.15529(8) 0.0353(3) Uani 1 1 d . . . Cl2 Cl 0.36640(11) 0.30236(12) -0.01483(9) 0.0391(3) Uani 1 1 d . . . Cl3 Cl 0.5507(2) -0.2428(2) 0.2861(2) 0.1076(8) Uani 1 1 d . . . Cl4 Cl 0.8329(2) -0.2914(2) 0.26883(18) 0.0923(7) Uani 1 1 d . . . Cl5 Cl 0.7767(4) 0.2613(4) 0.3625(4) 0.0808(6) Uani 0.50 1 d PD B 1 Cl6 Cl 0.9461(4) 0.3914(3) 0.3253(4) 0.0808(6) Uani 0.50 1 d PD B 1 Cl5B Cl 0.8072(4) 0.3044(4) 0.4060(3) 0.0808(6) Uani 0.50 1 d PD B 2 Cl6B Cl 0.9567(4) 0.3745(3) 0.2464(4) 0.0808(6) Uani 0.50 1 d PD B 2 Pd1 Pd 0.54189(3) 0.35890(3) -0.04012(2) 0.02588(10) Uani 1 1 d . . . H2N H 0.637(6) 0.267(5) 0.119(4) 0.047(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.033(2) 0.037(3) 0.033(2) 0.0029(19) -0.0012(19) -0.015(2) C2 0.035(3) 0.042(3) 0.046(3) 0.008(2) 0.001(2) -0.020(2) C3 0.030(2) 0.040(3) 0.041(3) -0.005(2) 0.0046(19) -0.022(2) C4 0.025(2) 0.034(2) 0.030(2) -0.0061(18) 0.0047(17) -0.0159(18) C5 0.020(2) 0.042(3) 0.039(2) -0.005(2) 0.0013(18) -0.0147(19) C6 0.0188(19) 0.037(2) 0.033(2) -0.0030(19) -0.0014(16) -0.0103(17) C7 0.0224(19) 0.035(2) 0.0217(19) -0.0067(17) 0.0016(15) -0.0140(17) C8 0.026(2) 0.032(2) 0.026(2) -0.0056(17) -0.0014(16) -0.0125(18) C9 0.030(2) 0.033(2) 0.032(2) 0.0002(18) -0.0044(18) -0.0168(19) C10 0.028(2) 0.032(2) 0.032(2) -0.0005(18) -0.0040(17) -0.0184(18) C11 0.0219(18) 0.031(2) 0.0217(18) -0.0048(16) -0.0001(15) -0.0142(17) C12 0.0230(19) 0.031(2) 0.0234(19) -0.0069(16) 0.0026(15) -0.0136(17) C13 0.035(2) 0.039(3) 0.042(3) -0.009(2) -0.004(2) -0.018(2) C14 0.026(2) 0.047(3) 0.032(2) 0.010(2) -0.0090(18) -0.022(2) C15 0.039(3) 0.059(3) 0.046(3) 0.007(3) -0.010(2) -0.032(3) C16 0.040(3) 0.072(4) 0.055(3) 0.023(3) -0.015(3) -0.040(3) C17 0.027(2) 0.068(4) 0.052(3) 0.024(3) -0.001(2) -0.021(3) C18 0.023(2) 0.050(3) 0.034(2) 0.019(2) -0.0019(18) -0.009(2) C19 0.038(3) 0.048(3) 0.036(3) 0.018(2) 0.011(2) 0.001(2) C20 0.048(4) 0.100(6) 0.066(5) 0.003(4) 0.021(3) -0.013(4) C21 0.076(6) 0.114(8) 0.070(5) -0.006(5) 0.044(5) 0.000(5) C22 0.114(7) 0.067(5) 0.062(5) 0.003(4) 0.045(5) -0.002(5) C23 0.113(7) 0.065(5) 0.067(5) -0.018(4) 0.039(5) -0.035(5) C24 0.073(4) 0.055(4) 0.054(4) -0.007(3) 0.031(3) -0.025(3) C25 0.026(2) 0.029(2) 0.028(2) -0.0033(17) 0.0020(16) -0.0105(17) C26 0.036(2) 0.033(2) 0.041(3) -0.011(2) -0.004(2) -0.011(2) C27 0.047(3) 0.030(3) 0.048(3) -0.009(2) -0.004(2) -0.007(2) C28 0.033(2) 0.030(2) 0.043(3) 0.001(2) -0.003(2) -0.005(2) C29 0.0233(19) 0.029(2) 0.029(2) 0.0016(17) 0.0001(16) -0.0106(17) C30 0.028(2) 0.033(2) 0.028(2) 0.0041(17) -0.0017(17) -0.0170(18) C31 0.031(2) 0.038(3) 0.036(2) 0.005(2) -0.0055(19) -0.012(2) C32 0.041(3) 0.057(3) 0.038(3) 0.013(2) -0.018(2) -0.026(3) C33 0.062(4) 0.061(4) 0.034(3) -0.002(2) -0.011(2) -0.041(3) C34 0.050(3) 0.048(3) 0.036(3) -0.009(2) 0.003(2) -0.027(3) C35 0.027(2) 0.037(2) 0.033(2) -0.0016(19) 0.0001(18) -0.0138(19) C36 0.063(4) 0.050(3) 0.050(3) -0.011(3) 0.004(3) -0.028(3) C37 0.058(4) 0.046(3) 0.040(3) -0.012(2) -0.009(3) -0.002(3) N1 0.0229(16) 0.0306(19) 0.0236(17) -0.0043(14) 0.0000(13) -0.0105(15) N2 0.0217(16) 0.0308(19) 0.0226(17) -0.0021(14) 0.0002(13) -0.0143(15) N3 0.0238(18) 0.039(2) 0.0286(19) 0.0093(16) -0.0013(14) -0.0110(16) N4 0.0218(16) 0.0269(18) 0.0269(18) 0.0001(14) -0.0017(13) -0.0093(14) Cl1 0.0300(5) 0.0391(6) 0.0350(6) 0.0017(5) -0.0080(4) -0.0135(5) Cl2 0.0267(5) 0.0567(8) 0.0370(6) 0.0051(5) -0.0054(4) -0.0237(5) Cl3 0.0884(16) 0.0946(17) 0.120(2) -0.0403(15) 0.0405(14) -0.0101(13) Cl4 0.1062(16) 0.1065(17) 0.1105(17) -0.0591(14) 0.0421(13) -0.0792(15) Cl5 0.0606(10) 0.0664(12) 0.1038(17) 0.0024(12) 0.0142(12) -0.0205(9) Cl6 0.0606(10) 0.0664(12) 0.1038(17) 0.0024(12) 0.0142(12) -0.0205(9) Cl5B 0.0606(10) 0.0664(12) 0.1038(17) 0.0024(12) 0.0142(12) -0.0205(9) Cl6B 0.0606(10) 0.0664(12) 0.1038(17) 0.0024(12) 0.0142(12) -0.0205(9) Pd1 0.02054(15) 0.03447(19) 0.02373(16) -0.00171(12) -0.00178(11) -0.01275(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.327(6) . ? C1 C2 1.402(7) . ? C1 H1 0.9500 . ? C2 C3 1.367(7) . ? C2 H2 0.9500 . ? C3 C4 1.417(6) . ? C3 H3 0.9500 . ? C4 C5 1.408(6) . ? C4 C12 1.423(5) . ? C5 C6 1.367(6) . ? C5 H5 0.9500 . ? C6 C7 1.424(6) . ? C6 H6 0.9500 . ? C7 C11 1.377(6) . ? C7 C8 1.469(6) . ? C8 C9 1.335(6) . ? C8 C25 1.491(6) . ? C9 C10 1.518(6) . ? C9 H9 0.9500 . ? C10 N2 1.499(5) . ? C10 C13 1.527(6) . ? C10 C14 1.532(6) . ? C11 C12 1.403(6) . ? C11 N2 1.462(5) . ? C12 N1 1.373(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N3 1.326(7) . ? C14 C15 1.394(7) . ? C15 C16 1.388(8) . ? C15 H15 0.9500 . ? C16 C17 1.369(9) . ? C16 H16 0.9500 . ? C17 C18 1.399(8) . ? C17 H17 0.9500 . ? C18 N3 1.347(6) . ? C18 C19 1.483(9) . ? C19 C24 1.364(9) . ? C19 C20 1.397(8) . ? C20 C21 1.385(13) . ? C20 H20 0.9500 . ? C21 C22 1.350(14) . ? C21 H21 0.9500 . ? C22 C23 1.368(11) . ? C22 H22 0.9500 . ? C23 C24 1.392(10) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 N4 1.341(6) . ? C25 C26 1.390(6) . ? C26 C27 1.378(7) . ? C26 H26 0.9500 . ? C27 C28 1.381(7) . ? C27 H27 0.9500 . ? C28 C29 1.391(6) . ? C28 H28 0.9500 . ? C29 N4 1.348(5) . ? C29 C30 1.492(6) . ? C30 C35 1.393(7) . ? C30 C31 1.401(6) . ? C31 C32 1.383(7) . ? C31 H31 0.9500 . ? C32 C33 1.382(8) . ? C32 H32 0.9500 . ? C33 C34 1.384(8) . ? C33 H33 0.9500 . ? C34 C35 1.385(7) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 Cl3 1.736(7) . ? C36 Cl4 1.759(6) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 Cl6B 1.602(6) . ? C37 Cl5 1.625(6) . ? C37 Cl5B 1.805(6) . ? C37 Cl6 1.854(6) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? N1 Pd1 2.028(3) . ? N2 Pd1 2.111(4) . ? N2 H2N 0.86(6) . ? Cl1 Pd1 2.2910(12) . ? Cl2 Pd1 2.2976(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.3(4) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 120.2(4) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.2(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 123.6(4) . . ? C5 C4 C12 118.9(4) . . ? C3 C4 C12 117.5(4) . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 121.5(4) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C11 C7 C6 118.7(4) . . ? C11 C7 C8 119.0(4) . . ? C6 C7 C8 122.3(4) . . ? C9 C8 C7 118.2(4) . . ? C9 C8 C25 120.3(4) . . ? C7 C8 C25 121.3(4) . . ? C8 C9 C10 124.5(4) . . ? C8 C9 H9 117.8 . . ? C10 C9 H9 117.8 . . ? N2 C10 C9 111.6(3) . . ? N2 C10 C13 108.9(4) . . ? C9 C10 C13 108.4(4) . . ? N2 C10 C14 107.3(4) . . ? C9 C10 C14 105.6(4) . . ? C13 C10 C14 115.0(4) . . ? C7 C11 C12 120.9(4) . . ? C7 C11 N2 122.5(4) . . ? C12 C11 N2 116.6(4) . . ? N1 C12 C11 118.5(4) . . ? N1 C12 C4 121.7(4) . . ? C11 C12 C4 119.8(4) . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 123.3(5) . . ? N3 C14 C10 115.9(4) . . ? C15 C14 C10 120.4(5) . . ? C16 C15 C14 116.7(6) . . ? C16 C15 H15 121.6 . . ? C14 C15 H15 121.6 . . ? C17 C16 C15 120.5(5) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.3(5) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? N3 C18 C17 120.3(6) . . ? N3 C18 C19 117.1(5) . . ? C17 C18 C19 122.5(5) . . ? C24 C19 C20 116.8(7) . . ? C24 C19 C18 121.1(5) . . ? C20 C19 C18 122.1(7) . . ? C21 C20 C19 120.9(8) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C20 121.2(7) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 118.8(9) . . ? C21 C22 H22 120.6 . . ? C23 C22 H22 120.6 . . ? C22 C23 C24 120.5(9) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C19 C24 C23 121.7(6) . . ? C19 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? N4 C25 C26 123.1(4) . . ? N4 C25 C8 116.4(4) . . ? C26 C25 C8 120.6(4) . . ? C27 C26 C25 118.5(5) . . ? C27 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? C26 C27 C28 119.2(5) . . ? C26 C27 H27 120.4 . . ? C28 C27 H27 120.4 . . ? C27 C28 C29 119.3(5) . . ? C27 C28 H28 120.4 . . ? C29 C28 H28 120.4 . . ? N4 C29 C28 122.0(4) . . ? N4 C29 C30 116.1(4) . . ? C28 C29 C30 121.8(4) . . ? C35 C30 C31 118.6(4) . . ? C35 C30 C29 120.2(4) . . ? C31 C30 C29 121.2(4) . . ? C32 C31 C30 120.2(5) . . ? C32 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? C33 C32 C31 120.5(5) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C34 119.9(5) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C33 C34 C35 119.9(5) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C30 120.9(4) . . ? C34 C35 H35 119.6 . . ? C30 C35 H35 119.6 . . ? Cl3 C36 Cl4 112.6(3) . . ? Cl3 C36 H36A 109.1 . . ? Cl4 C36 H36A 109.1 . . ? Cl3 C36 H36B 109.1 . . ? Cl4 C36 H36B 109.1 . . ? H36A C36 H36B 107.8 . . ? Cl6B C37 Cl5 149.9(4) . . ? Cl6B C37 Cl5B 117.2(4) . . ? Cl5 C37 Cl6 114.3(3) . . ? Cl5B C37 Cl6 80.1(3) . . ? Cl6B C37 H37A 80.7 . . ? Cl5 C37 H37A 108.7 . . ? Cl5B C37 H37A 127.2 . . ? Cl6 C37 H37A 108.7 . . ? Cl6B C37 H37B 94.6 . . ? Cl5 C37 H37B 108.7 . . ? Cl5B C37 H37B 118.7 . . ? Cl6 C37 H37B 108.7 . . ? H37A C37 H37B 107.6 . . ? C1 N1 C12 119.0(4) . . ? C1 N1 Pd1 127.7(3) . . ? C12 N1 Pd1 113.3(3) . . ? C11 N2 C10 113.5(3) . . ? C11 N2 Pd1 107.9(2) . . ? C10 N2 Pd1 121.2(3) . . ? C11 N2 H2N 107(4) . . ? C10 N2 H2N 106(4) . . ? Pd1 N2 H2N 99(4) . . ? C14 N3 C18 119.7(4) . . ? C25 N4 C29 118.0(4) . . ? N1 Pd1 N2 82.09(13) . . ? N1 Pd1 Cl1 93.27(11) . . ? N2 Pd1 Cl1 174.44(10) . . ? N1 Pd1 Cl2 177.58(11) . . ? N2 Pd1 Cl2 96.37(9) . . ? Cl1 Pd1 Cl2 88.37(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.2(8) . . . . ? C1 C2 C3 C4 -0.9(8) . . . . ? C2 C3 C4 C5 177.9(5) . . . . ? C2 C3 C4 C12 -0.5(7) . . . . ? C3 C4 C5 C6 -177.9(5) . . . . ? C12 C4 C5 C6 0.5(7) . . . . ? C4 C5 C6 C7 -1.9(7) . . . . ? C5 C6 C7 C11 0.2(7) . . . . ? C5 C6 C7 C8 178.3(4) . . . . ? C11 C7 C8 C9 11.1(6) . . . . ? C6 C7 C8 C9 -167.0(4) . . . . ? C11 C7 C8 C25 -172.9(4) . . . . ? C6 C7 C8 C25 9.0(6) . . . . ? C7 C8 C9 C10 -2.3(7) . . . . ? C25 C8 C9 C10 -178.4(4) . . . . ? C8 C9 C10 N2 -21.9(6) . . . . ? C8 C9 C10 C13 98.1(5) . . . . ? C8 C9 C10 C14 -138.2(5) . . . . ? C6 C7 C11 C12 2.7(6) . . . . ? C8 C7 C11 C12 -175.4(4) . . . . ? C6 C7 C11 N2 -175.2(4) . . . . ? C8 C7 C11 N2 6.7(6) . . . . ? C7 C11 C12 N1 174.3(4) . . . . ? N2 C11 C12 N1 -7.7(6) . . . . ? C7 C11 C12 C4 -4.0(6) . . . . ? N2 C11 C12 C4 174.0(4) . . . . ? C5 C4 C12 N1 -175.9(4) . . . . ? C3 C4 C12 N1 2.6(6) . . . . ? C5 C4 C12 C11 2.4(6) . . . . ? C3 C4 C12 C11 -179.1(4) . . . . ? N2 C10 C14 N3 -31.1(5) . . . . ? C9 C10 C14 N3 88.0(5) . . . . ? C13 C10 C14 N3 -152.5(4) . . . . ? N2 C10 C14 C15 155.5(4) . . . . ? C9 C10 C14 C15 -85.3(5) . . . . ? C13 C10 C14 C15 34.1(6) . . . . ? N3 C14 C15 C16 3.2(7) . . . . ? C10 C14 C15 C16 176.0(4) . . . . ? C14 C15 C16 C17 -1.7(8) . . . . ? C15 C16 C17 C18 -0.5(8) . . . . ? C16 C17 C18 N3 1.5(7) . . . . ? C16 C17 C18 C19 -177.2(5) . . . . ? N3 C18 C19 C24 -10.0(7) . . . . ? C17 C18 C19 C24 168.7(5) . . . . ? N3 C18 C19 C20 170.3(5) . . . . ? C17 C18 C19 C20 -11.0(8) . . . . ? C24 C19 C20 C21 1.6(10) . . . . ? C18 C19 C20 C21 -178.6(7) . . . . ? C19 C20 C21 C22 -0.8(13) . . . . ? C20 C21 C22 C23 -0.1(14) . . . . ? C21 C22 C23 C24 0.2(13) . . . . ? C20 C19 C24 C23 -1.5(10) . . . . ? C18 C19 C24 C23 178.7(6) . . . . ? C22 C23 C24 C19 0.7(12) . . . . ? C9 C8 C25 N4 -124.9(5) . . . . ? C7 C8 C25 N4 59.2(5) . . . . ? C9 C8 C25 C26 53.8(6) . . . . ? C7 C8 C25 C26 -122.0(5) . . . . ? N4 C25 C26 C27 1.2(7) . . . . ? C8 C25 C26 C27 -177.5(4) . . . . ? C25 C26 C27 C28 0.6(8) . . . . ? C26 C27 C28 C29 -1.1(8) . . . . ? C27 C28 C29 N4 -0.1(7) . . . . ? C27 C28 C29 C30 179.1(4) . . . . ? N4 C29 C30 C35 29.2(6) . . . . ? C28 C29 C30 C35 -150.1(4) . . . . ? N4 C29 C30 C31 -150.1(4) . . . . ? C28 C29 C30 C31 30.6(6) . . . . ? C35 C30 C31 C32 -1.0(7) . . . . ? C29 C30 C31 C32 178.3(4) . . . . ? C30 C31 C32 C33 0.5(7) . . . . ? C31 C32 C33 C34 0.4(8) . . . . ? C32 C33 C34 C35 -0.8(8) . . . . ? C33 C34 C35 C30 0.3(7) . . . . ? C31 C30 C35 C34 0.6(7) . . . . ? C29 C30 C35 C34 -178.8(4) . . . . ? C2 C1 N1 C12 1.8(7) . . . . ? C2 C1 N1 Pd1 -176.7(4) . . . . ? C11 C12 N1 C1 178.4(4) . . . . ? C4 C12 N1 C1 -3.3(6) . . . . ? C11 C12 N1 Pd1 -2.9(5) . . . . ? C4 C12 N1 Pd1 175.4(3) . . . . ? C7 C11 N2 C10 -31.4(5) . . . . ? C12 C11 N2 C10 150.6(4) . . . . ? C7 C11 N2 Pd1 -168.6(3) . . . . ? C12 C11 N2 Pd1 13.4(4) . . . . ? C9 C10 N2 C11 36.4(5) . . . . ? C13 C10 N2 C11 -83.2(4) . . . . ? C14 C10 N2 C11 151.7(3) . . . . ? C9 C10 N2 Pd1 167.3(3) . . . . ? C13 C10 N2 Pd1 47.7(4) . . . . ? C14 C10 N2 Pd1 -77.4(4) . . . . ? C15 C14 N3 C18 -2.3(7) . . . . ? C10 C14 N3 C18 -175.4(4) . . . . ? C17 C18 N3 C14 -0.1(7) . . . . ? C19 C18 N3 C14 178.6(4) . . . . ? C26 C25 N4 C29 -2.3(6) . . . . ? C8 C25 N4 C29 176.4(4) . . . . ? C28 C29 N4 C25 1.7(6) . . . . ? C30 C29 N4 C25 -177.5(4) . . . . ? C1 N1 Pd1 N2 -173.3(4) . . . . ? C12 N1 Pd1 N2 8.1(3) . . . . ? C1 N1 Pd1 Cl1 3.6(4) . . . . ? C12 N1 Pd1 Cl1 -174.9(3) . . . . ? C11 N2 Pd1 N1 -11.3(3) . . . . ? C10 N2 Pd1 N1 -144.6(3) . . . . ? C11 N2 Pd1 Cl2 166.8(2) . . . . ? C10 N2 Pd1 Cl2 33.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N N3 0.86(6) 2.16(6) 2.663(5) 117(5) . N2 H2N Cl1 0.86(6) 2.89(6) 3.518(4) 131(5) 2_665 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.299 _refine_diff_density_min -1.899 _refine_diff_density_rms 0.120