# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jan Bernhammer' _publ_contact_author_email chmhhv@nus.edu.sg loop_ _publ_author_name J.Bernhammer 'Han Vinh Huynh' data_b238 _database_code_depnum_ccdc_archive 'CCDC 870361' #TrackingRef '- crystallographic data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 Br2 N4 O Pd' _chemical_formula_weight 656.74 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 9.0465(6) _cell_length_b 16.5328(10) _cell_length_c 35.937(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5374.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3781 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 22.76 _exptl_crystal_description 'Thin plate' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2608 _exptl_absorpt_coefficient_mu 3.686 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2158 _exptl_absorpt_correction_T_max 0.7569 _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 35964 _diffrn_reflns_av_R_equivalents 0.0892 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6171 _reflns_number_gt 4501 _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^)+(0.0494P)^2^+28.7429P] 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 6171 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.1648 _refine_ls_wR_factor_gt 0.1552 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.141 _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 0.53490(6) 0.56151(3) 0.626946(13) 0.02653(15) Uani 1 1 d . . . Br1 Br 0.69718(10) 0.49386(6) 0.58277(2) 0.0541(3) Uani 1 1 d . . . Br2 Br 0.38302(13) 0.62158(6) 0.67520(2) 0.0629(3) Uani 1 1 d . . . O1 O 0.4223(7) 0.7360(4) 0.50612(16) 0.0575(17) Uani 1 1 d . . . N1 N 0.6324(7) 0.4495(3) 0.68568(15) 0.0321(13) Uani 1 1 d . . . N2 N 0.4537(6) 0.3978(3) 0.65258(17) 0.0332(13) Uani 1 1 d . . . N3 N 0.5259(7) 0.6657(3) 0.59321(16) 0.0329(13) Uani 1 1 d . . . N4 N 0.4498(7) 0.6636(3) 0.56017(16) 0.0347(14) Uani 1 1 d . . . C1 C 0.5416(7) 0.4633(4) 0.65711(18) 0.0273(14) Uani 1 1 d . . . C2 C 0.6059(8) 0.3725(5) 0.7007(2) 0.0377(17) Uani 1 1 d . . . C3 C 0.6694(11) 0.3296(6) 0.7296(3) 0.061(3) Uani 1 1 d . . . H3 H 0.7493 0.3508 0.7432 0.073 Uiso 1 1 calc R . . C4 C 0.6111(14) 0.2547(7) 0.7378(3) 0.084(4) Uani 1 1 d . . . H4 H 0.6486 0.2250 0.7580 0.101 Uiso 1 1 calc R . . C5 C 0.4963(12) 0.2222(6) 0.7161(4) 0.082(4) Uani 1 1 d . . . H5 H 0.4607 0.1702 0.7218 0.098 Uiso 1 1 calc R . . C6 C 0.4351(10) 0.2632(5) 0.6874(3) 0.063(3) Uani 1 1 d . . . H6 H 0.3576 0.2411 0.6733 0.075 Uiso 1 1 calc R . . C7 C 0.4925(8) 0.3403(4) 0.6796(2) 0.0378(18) Uani 1 1 d . . . C8 C 0.7486(9) 0.5061(5) 0.6980(2) 0.0422(18) Uani 1 1 d . . . H8 H 0.7351 0.5557 0.6829 0.051 Uiso 1 1 calc R . . C9 C 0.7250(13) 0.5313(7) 0.7382(3) 0.071(3) Uani 1 1 d . . . H9A H 0.6219 0.5450 0.7420 0.107 Uiso 1 1 calc R . . H9B H 0.7860 0.5781 0.7437 0.107 Uiso 1 1 calc R . . H9C H 0.7521 0.4870 0.7545 0.107 Uiso 1 1 calc R . . C10 C 0.8976(10) 0.4756(7) 0.6888(3) 0.070(3) Uani 1 1 d . . . H10A H 0.9206 0.4295 0.7045 0.105 Uiso 1 1 calc R . . H10B H 0.9699 0.5180 0.6929 0.105 Uiso 1 1 calc R . . H10C H 0.9003 0.4591 0.6629 0.105 Uiso 1 1 calc R . . C11 C 0.3379(8) 0.3924(5) 0.6238(2) 0.0443(19) Uani 1 1 d . . . H11 H 0.3356 0.4451 0.6107 0.053 Uiso 1 1 calc R . . C12 C 0.3765(13) 0.3285(6) 0.5951(3) 0.082(4) Uani 1 1 d . . . H12A H 0.4702 0.3419 0.5835 0.123 Uiso 1 1 calc R . . H12B H 0.2998 0.3265 0.5762 0.123 Uiso 1 1 calc R . . H12C H 0.3843 0.2762 0.6071 0.123 Uiso 1 1 calc R . . C13 C 0.1886(10) 0.3809(7) 0.6416(3) 0.073(3) Uani 1 1 d . . . H13A H 0.1841 0.3279 0.6531 0.110 Uiso 1 1 calc R . . H13B H 0.1121 0.3851 0.6227 0.110 Uiso 1 1 calc R . . H13C H 0.1733 0.4223 0.6603 0.110 Uiso 1 1 calc R . . C14 C 0.6140(9) 0.7292(5) 0.5913(2) 0.0414(18) Uani 1 1 d . . . C15 C 0.5964(9) 0.7710(4) 0.5578(2) 0.044(2) Uani 1 1 d . . . H15 H 0.6452 0.8182 0.5499 0.053 Uiso 1 1 calc R . . C16 C 0.4904(9) 0.7269(5) 0.5387(2) 0.0407(18) Uani 1 1 d . . . C17 C 0.7178(12) 0.7490(6) 0.6227(3) 0.070(3) Uani 1 1 d . . . H17A H 0.6624 0.7529 0.6458 0.106 Uiso 1 1 calc R . . H17B H 0.7663 0.8001 0.6178 0.106 Uiso 1 1 calc R . . H17C H 0.7915 0.7066 0.6249 0.106 Uiso 1 1 calc R . . C18 C 0.4720(12) 0.8006(6) 0.4836(2) 0.063(3) Uani 1 1 d . . . H18A H 0.4564 0.8514 0.4966 0.095 Uiso 1 1 calc R . . H18B H 0.4173 0.8009 0.4604 0.095 Uiso 1 1 calc R . . H18C H 0.5765 0.7939 0.4784 0.095 Uiso 1 1 calc R . . C19 C 0.3330(8) 0.6072(4) 0.55429(19) 0.0326(16) Uani 1 1 d . . . C20 C 0.2223(8) 0.6006(4) 0.5810(2) 0.0343(16) Uani 1 1 d . . . H20 H 0.2248 0.6332 0.6025 0.041 Uiso 1 1 calc R . . C21 C 0.1099(9) 0.5464(5) 0.5760(2) 0.047(2) Uani 1 1 d . . . H21 H 0.0348 0.5420 0.5939 0.056 Uiso 1 1 calc R . . C22 C 0.1062(10) 0.4988(6) 0.5449(2) 0.054(2) Uani 1 1 d . . . H22 H 0.0277 0.4623 0.5416 0.065 Uiso 1 1 calc R . . C23 C 0.2170(10) 0.5037(5) 0.5184(2) 0.052(2) Uani 1 1 d . . . H23 H 0.2158 0.4696 0.4975 0.062 Uiso 1 1 calc R . . C24 C 0.3304(9) 0.5600(5) 0.5232(2) 0.0414(18) Uani 1 1 d . . . H24 H 0.4047 0.5654 0.5051 0.050 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 0.0316(3) 0.0273(2) 0.0207(2) 0.0019(2) 0.0000(2) -0.0009(2) Br1 0.0487(5) 0.0722(6) 0.0412(5) 0.0006(4) 0.0163(4) 0.0109(5) Br2 0.0904(8) 0.0624(6) 0.0360(5) 0.0001(4) 0.0143(5) 0.0336(5) O1 0.071(4) 0.055(3) 0.046(3) 0.029(3) -0.017(3) -0.021(3) N1 0.042(4) 0.034(3) 0.021(3) 0.004(2) -0.003(3) -0.008(3) N2 0.023(3) 0.032(3) 0.044(4) 0.005(3) -0.001(3) 0.001(3) N3 0.038(3) 0.031(3) 0.030(3) 0.007(2) -0.006(3) -0.005(3) N4 0.034(3) 0.036(3) 0.034(3) 0.009(3) -0.007(3) -0.007(3) C1 0.022(3) 0.032(3) 0.028(3) 0.006(3) 0.011(3) 0.005(3) C2 0.029(4) 0.042(4) 0.042(4) 0.013(3) 0.005(3) 0.005(3) C3 0.058(6) 0.069(6) 0.057(6) 0.035(5) -0.005(5) 0.010(5) C4 0.093(9) 0.070(7) 0.088(8) 0.059(6) -0.003(7) 0.013(7) C5 0.063(7) 0.063(6) 0.119(10) 0.060(7) 0.002(7) -0.009(5) C6 0.040(5) 0.042(5) 0.106(8) 0.018(5) -0.005(5) -0.009(4) C7 0.030(4) 0.029(4) 0.055(5) 0.012(3) 0.006(3) 0.005(3) C8 0.045(4) 0.041(4) 0.041(4) -0.005(3) -0.005(4) -0.010(4) C9 0.074(7) 0.096(8) 0.044(5) -0.015(5) -0.008(5) -0.003(6) C10 0.038(5) 0.096(8) 0.077(7) -0.008(6) -0.008(5) -0.006(5) C11 0.031(4) 0.043(4) 0.058(5) -0.002(4) -0.014(4) 0.000(3) C12 0.083(8) 0.071(7) 0.093(8) -0.038(6) -0.037(7) -0.004(6) C13 0.031(5) 0.079(7) 0.111(9) 0.017(7) -0.011(5) -0.003(5) C14 0.046(5) 0.037(4) 0.041(4) 0.006(3) -0.007(4) -0.010(4) C15 0.051(5) 0.030(4) 0.051(5) 0.015(3) -0.002(4) -0.018(4) C16 0.043(5) 0.041(4) 0.038(4) 0.013(3) -0.003(3) -0.006(4) C17 0.085(8) 0.069(6) 0.057(6) 0.015(5) -0.029(5) -0.039(6) C18 0.089(7) 0.058(5) 0.042(5) 0.019(4) 0.004(5) -0.018(5) C19 0.033(4) 0.035(4) 0.029(4) 0.015(3) -0.012(3) -0.005(3) C20 0.040(4) 0.033(4) 0.030(4) 0.007(3) -0.007(3) 0.004(3) C21 0.035(4) 0.059(5) 0.047(5) 0.020(4) -0.003(4) -0.004(4) C22 0.050(5) 0.066(6) 0.045(5) 0.008(4) -0.012(4) -0.029(5) C23 0.056(6) 0.055(5) 0.045(5) -0.008(4) -0.005(4) -0.006(4) C24 0.041(4) 0.050(4) 0.034(4) 0.000(4) 0.004(3) -0.005(4) _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 1.953(6) . ? Pd1 N3 2.108(5) . ? Pd1 Br2 2.4251(10) . ? Pd1 Br1 2.4346(10) . ? O1 C16 1.331(9) . ? O1 C18 1.414(9) . ? N1 C1 1.335(9) . ? N1 C2 1.402(9) . ? N1 C8 1.476(10) . ? N2 C1 1.353(9) . ? N2 C7 1.405(9) . ? N2 C11 1.476(9) . ? N3 C14 1.320(9) . ? N3 N4 1.373(8) . ? N4 C16 1.351(9) . ? N4 C19 1.424(9) . ? C2 C7 1.381(11) . ? C2 C3 1.384(11) . ? C3 C4 1.379(14) . ? C4 C5 1.405(16) . ? C5 C6 1.354(14) . ? C6 C7 1.405(11) . ? C8 C10 1.477(13) . ? C8 C9 1.520(12) . ? C11 C13 1.507(12) . ? C11 C12 1.518(12) . ? C14 C15 1.399(10) . ? C14 C17 1.505(11) . ? C15 C16 1.386(11) . ? C19 C24 1.362(10) . ? C19 C20 1.393(10) . ? C20 C21 1.367(11) . ? C21 C22 1.365(12) . ? C22 C23 1.385(12) . ? C23 C24 1.397(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 N3 178.5(3) . . ? C1 Pd1 Br2 87.76(19) . . ? N3 Pd1 Br2 93.13(17) . . ? C1 Pd1 Br1 87.79(19) . . ? N3 Pd1 Br1 91.36(17) . . ? Br2 Pd1 Br1 174.94(4) . . ? C16 O1 C18 116.2(7) . . ? C1 N1 C2 110.2(6) . . ? C1 N1 C8 124.1(6) . . ? C2 N1 C8 125.6(6) . . ? C1 N2 C7 108.2(6) . . ? C1 N2 C11 123.4(6) . . ? C7 N2 C11 128.5(6) . . ? C14 N3 N4 106.2(6) . . ? C14 N3 Pd1 131.0(5) . . ? N4 N3 Pd1 119.7(4) . . ? C16 N4 N3 109.7(6) . . ? C16 N4 C19 128.6(6) . . ? N3 N4 C19 121.1(5) . . ? N1 C1 N2 108.5(6) . . ? N1 C1 Pd1 126.1(5) . . ? N2 C1 Pd1 125.5(5) . . ? C7 C2 C3 121.5(8) . . ? C7 C2 N1 105.5(6) . . ? C3 C2 N1 133.1(8) . . ? C4 C3 C2 117.5(10) . . ? C3 C4 C5 120.6(9) . . ? C6 C5 C4 122.2(9) . . ? C5 C6 C7 117.1(9) . . ? C2 C7 C6 121.1(8) . . ? C2 C7 N2 107.7(6) . . ? C6 C7 N2 131.2(8) . . ? N1 C8 C10 111.5(7) . . ? N1 C8 C9 111.0(7) . . ? C10 C8 C9 115.8(8) . . ? N2 C11 C13 110.2(7) . . ? N2 C11 C12 110.8(7) . . ? C13 C11 C12 114.0(8) . . ? N3 C14 C15 111.6(7) . . ? N3 C14 C17 120.7(7) . . ? C15 C14 C17 127.6(7) . . ? C16 C15 C14 104.1(6) . . ? O1 C16 N4 117.7(7) . . ? O1 C16 C15 134.0(7) . . ? N4 C16 C15 108.3(7) . . ? C24 C19 C20 120.5(7) . . ? C24 C19 N4 120.6(7) . . ? C20 C19 N4 118.8(7) . . ? C21 C20 C19 119.6(7) . . ? C22 C21 C20 120.4(8) . . ? C21 C22 C23 120.7(8) . . ? C22 C23 C24 119.0(8) . . ? C19 C24 C23 119.8(8) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.679 _refine_diff_density_min -1.165 _refine_diff_density_rms 0.148 data_b246 _database_code_depnum_ccdc_archive 'CCDC 870362' #TrackingRef '- crystallographic data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 Br3 Cl3 N4 Pd' _chemical_formula_weight 839.01 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 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 11.706(4) _cell_length_b 15.947(5) _cell_length_c 16.887(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3152.3(18) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3794 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 22.07 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 4.667 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2037 _exptl_absorpt_correction_T_max 0.6526 _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 21131 _diffrn_reflns_av_R_equivalents 0.1014 _diffrn_reflns_av_sigmaI/netI 0.1254 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7213 _reflns_number_gt 4792 _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. Restraints in thermal parameters (ISOR of Shelxtl) were applied to the phenyl ring. ; _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^)+(0.0437P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.057(13) _refine_ls_number_reflns 7213 _refine_ls_number_parameters 319 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.948 _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 0.70048(5) 0.21414(4) 0.27092(3) 0.02869(14) Uani 1 1 d . . . Br1 Br 0.54262(8) 0.25340(6) 0.18655(5) 0.0488(2) Uani 1 1 d . . . Br2 Br 0.84754(8) 0.17418(7) 0.36399(5) 0.0543(3) Uani 1 1 d . . . Br3 Br 0.98618(10) 0.48572(7) 0.12511(7) 0.0705(3) Uani 1 1 d . . . N1 N 0.5408(5) 0.1789(4) 0.4027(3) 0.0312(14) Uani 1 1 d . . . N2 N 0.5606(5) 0.0728(4) 0.3225(4) 0.0342(15) Uani 1 1 d . . . N3 N 0.8155(5) 0.2813(4) 0.1990(3) 0.0359(15) Uani 1 1 d . . . N4 N 0.8532(6) 0.2536(4) 0.1269(3) 0.0392(16) Uani 1 1 d . . . C1 C 0.5927(7) 0.1518(5) 0.3364(4) 0.0311(18) Uani 1 1 d . . . C2 C 0.4710(7) 0.1157(5) 0.4318(4) 0.0320(17) Uani 1 1 d . . . C3 C 0.3963(8) 0.1128(6) 0.4962(5) 0.045(2) Uani 1 1 d . . . H3 H 0.3873 0.1585 0.5309 0.054 Uiso 1 1 calc R . . C4 C 0.3355(8) 0.0374(6) 0.5062(5) 0.054(3) Uani 1 1 d . . . H4 H 0.2844 0.0323 0.5489 0.065 Uiso 1 1 calc R . . C5 C 0.3485(8) -0.0284(6) 0.4557(5) 0.050(2) Uani 1 1 d . . . H5 H 0.3050 -0.0770 0.4644 0.060 Uiso 1 1 calc R . . C6 C 0.4217(8) -0.0271(6) 0.3930(5) 0.047(2) Uani 1 1 d . . . H6 H 0.4297 -0.0735 0.3591 0.056 Uiso 1 1 calc R . . C7 C 0.4852(7) 0.0473(5) 0.3813(4) 0.0355(19) Uani 1 1 d . . . C8 C 0.5570(8) 0.2647(5) 0.4345(4) 0.039(2) Uani 1 1 d . . . H8 H 0.6134 0.2934 0.4003 0.047 Uiso 1 1 calc R . . C9 C 0.4462(9) 0.3127(5) 0.4288(5) 0.056(3) Uani 1 1 d . . . H9A H 0.4270 0.3215 0.3735 0.085 Uiso 1 1 calc R . . H9B H 0.4545 0.3665 0.4549 0.085 Uiso 1 1 calc R . . H9C H 0.3858 0.2810 0.4543 0.085 Uiso 1 1 calc R . . C10 C 0.6062(8) 0.2617(6) 0.5175(5) 0.055(3) Uani 1 1 d . . . H10A H 0.5526 0.2340 0.5526 0.083 Uiso 1 1 calc R . . H10B H 0.6200 0.3183 0.5361 0.083 Uiso 1 1 calc R . . H10C H 0.6776 0.2308 0.5168 0.083 Uiso 1 1 calc R . . C11 C 0.5999(7) 0.0242(5) 0.2526(4) 0.041(2) Uani 1 1 d . . . H11 H 0.6523 0.0610 0.2224 0.049 Uiso 1 1 calc R . . C12 C 0.6677(8) -0.0510(6) 0.2774(6) 0.055(2) Uani 1 1 d . . . H12A H 0.7364 -0.0330 0.3045 0.082 Uiso 1 1 calc R . . H12B H 0.6883 -0.0835 0.2310 0.082 Uiso 1 1 calc R . . H12C H 0.6221 -0.0854 0.3127 0.082 Uiso 1 1 calc R . . C13 C 0.4984(9) 0.0058(7) 0.1989(6) 0.069(3) Uani 1 1 d . . . H13A H 0.4534 -0.0394 0.2213 0.103 Uiso 1 1 calc R . . H13B H 0.5257 -0.0106 0.1469 0.103 Uiso 1 1 calc R . . H13C H 0.4514 0.0556 0.1941 0.103 Uiso 1 1 calc R . . C14 C 0.8497(6) 0.3615(5) 0.2062(4) 0.0329(18) Uani 1 1 d . . . C15 C 0.9122(7) 0.3824(6) 0.1405(5) 0.046(2) Uani 1 1 d . . . C16 C 0.9146(7) 0.3154(6) 0.0906(5) 0.047(2) Uani 1 1 d . . . C17 C 0.8210(8) 0.4114(6) 0.2777(6) 0.056(3) Uani 1 1 d . . . H17A H 0.7729 0.3784 0.3126 0.085 Uiso 1 1 calc R . . H17B H 0.7806 0.4619 0.2620 0.085 Uiso 1 1 calc R . . H17C H 0.8907 0.4266 0.3052 0.085 Uiso 1 1 calc R . . C18 C 0.9728(9) 0.3010(8) 0.0142(6) 0.075(3) Uani 1 1 d . . . H18A H 1.0241 0.3473 0.0033 0.113 Uiso 1 1 calc R . . H18B H 0.9163 0.2971 -0.0277 0.113 Uiso 1 1 calc R . . H18C H 1.0161 0.2492 0.0168 0.113 Uiso 1 1 calc R . . C19 C 0.8385(5) 0.1693(3) 0.1038(4) 0.050(2) Uani 1 1 d GU . . C20 C 0.7801(6) 0.1508(4) 0.0343(3) 0.066(3) Uani 1 1 d GU . . H20 H 0.7489 0.1943 0.0036 0.080 Uiso 1 1 calc R . . C21 C 0.7677(6) 0.0679(5) 0.0103(4) 0.092(4) Uani 1 1 d GU . . H21 H 0.7282 0.0553 -0.0367 0.110 Uiso 1 1 calc R . . C22 C 0.8138(7) 0.0036(3) 0.0557(5) 0.086(4) Uani 1 1 d GU . . H22 H 0.8054 -0.0525 0.0395 0.104 Uiso 1 1 calc R . . C23 C 0.8722(6) 0.0222(4) 0.1252(4) 0.084(4) Uani 1 1 d GU . . H23 H 0.9034 -0.0213 0.1560 0.101 Uiso 1 1 calc R . . C24 C 0.8846(5) 0.1050(4) 0.1492(3) 0.059(3) Uani 1 1 d GU . . H24 H 0.9241 0.1176 0.1962 0.071 Uiso 1 1 calc R . . C1S C 0.2353(8) 0.2082(7) 0.2171(6) 0.062(3) Uani 1 1 d . . . H1S H 0.3071 0.2396 0.2085 0.075 Uiso 1 1 calc R . . Cl1 Cl 0.2095(4) 0.1469(2) 0.13333(18) 0.1041(11) Uani 1 1 d . . . Cl2 Cl 0.2528(3) 0.1450(2) 0.29940(18) 0.0965(11) Uani 1 1 d . . . Cl3 Cl 0.1270(3) 0.2797(2) 0.2326(3) 0.1333(17) 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 0.0286(3) 0.0332(3) 0.0243(2) -0.0057(2) 0.0017(2) -0.0002(3) Br1 0.0448(5) 0.0555(6) 0.0460(5) 0.0091(4) -0.0073(4) 0.0013(5) Br2 0.0446(6) 0.0707(7) 0.0478(5) -0.0063(5) -0.0129(4) 0.0072(5) Br3 0.0607(7) 0.0631(7) 0.0877(8) 0.0218(6) 0.0233(6) -0.0070(6) N1 0.030(4) 0.032(4) 0.032(3) -0.002(3) 0.001(3) 0.000(3) N2 0.038(4) 0.031(4) 0.034(3) -0.005(3) 0.002(3) 0.003(3) N3 0.029(4) 0.048(4) 0.031(3) -0.008(3) 0.003(2) -0.003(3) N4 0.034(4) 0.053(4) 0.031(3) -0.013(3) 0.006(3) -0.006(3) C1 0.039(4) 0.036(5) 0.018(3) -0.001(3) 0.000(3) 0.005(4) C2 0.032(4) 0.035(5) 0.029(4) 0.003(3) 0.004(3) -0.004(4) C3 0.045(5) 0.055(6) 0.035(4) 0.007(4) 0.006(4) -0.008(5) C4 0.056(6) 0.070(7) 0.037(5) 0.012(5) 0.007(4) -0.014(5) C5 0.052(6) 0.034(5) 0.063(6) 0.002(4) 0.010(5) -0.019(4) C6 0.059(6) 0.036(5) 0.046(5) 0.006(4) 0.001(4) -0.013(4) C7 0.046(5) 0.029(4) 0.032(4) -0.003(3) -0.006(3) 0.003(4) C8 0.054(6) 0.028(5) 0.035(4) -0.008(3) 0.009(4) -0.011(4) C9 0.091(8) 0.032(5) 0.046(5) 0.002(4) 0.013(5) 0.003(5) C10 0.044(6) 0.068(7) 0.055(5) -0.030(5) -0.002(4) -0.005(5) C11 0.043(5) 0.038(5) 0.041(5) -0.010(4) 0.005(3) -0.006(4) C12 0.042(5) 0.045(6) 0.076(6) -0.009(5) 0.005(5) 0.004(4) C13 0.075(8) 0.069(7) 0.063(6) -0.030(5) 0.010(5) 0.004(6) C14 0.021(4) 0.042(5) 0.036(4) 0.001(3) 0.003(3) -0.001(4) C15 0.034(5) 0.052(6) 0.051(5) -0.002(5) 0.005(4) 0.000(4) C16 0.030(5) 0.079(7) 0.031(4) 0.013(4) 0.003(3) -0.006(5) C17 0.064(7) 0.042(6) 0.063(6) -0.004(5) 0.009(5) -0.017(5) C18 0.060(7) 0.114(10) 0.052(6) 0.003(6) 0.021(5) -0.005(7) C19 0.030(4) 0.075(6) 0.044(4) -0.018(4) 0.009(3) -0.002(4) C20 0.057(6) 0.076(6) 0.066(5) -0.027(5) -0.003(5) -0.012(5) C21 0.081(7) 0.106(8) 0.088(7) -0.042(6) 0.000(6) -0.009(6) C22 0.077(7) 0.079(7) 0.103(7) -0.047(6) 0.025(6) -0.010(6) C23 0.067(6) 0.087(7) 0.099(7) -0.020(6) 0.012(6) 0.018(6) C24 0.054(5) 0.059(6) 0.065(5) -0.025(5) 0.008(4) 0.001(5) C1S 0.033(5) 0.065(7) 0.090(7) 0.011(6) -0.008(5) -0.011(5) Cl1 0.118(3) 0.130(3) 0.0646(18) -0.0114(18) -0.013(2) -0.013(3) Cl2 0.115(3) 0.108(3) 0.0663(18) 0.0095(16) -0.0071(17) 0.021(2) Cl3 0.072(2) 0.079(2) 0.249(5) -0.029(3) -0.043(3) 0.0209(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 C1 1.950(8) . ? Pd1 N3 2.107(6) . ? Pd1 Br1 2.4159(12) . ? Pd1 Br2 2.4164(12) . ? Br3 C15 1.879(9) . ? N1 C1 1.346(9) . ? N1 C2 1.387(9) . ? N1 C8 1.483(9) . ? N2 C1 1.335(10) . ? N2 C7 1.389(10) . ? N2 C11 1.485(9) . ? N3 C14 1.344(10) . ? N3 N4 1.368(8) . ? N4 C16 1.364(11) . ? N4 C19 1.411(8) . ? C2 C7 1.395(10) . ? C2 C3 1.396(11) . ? C3 C4 1.409(12) . ? C4 C5 1.361(12) . ? C5 C6 1.362(11) . ? C6 C7 1.413(11) . ? C8 C9 1.509(13) . ? C8 C10 1.515(12) . ? C11 C12 1.498(12) . ? C11 C13 1.524(12) . ? C14 C15 1.371(11) . ? C14 C17 1.486(11) . ? C15 C16 1.362(13) . ? C16 C18 1.477(12) . ? C19 C20 1.3900 . ? C19 C24 1.3900 . ? C20 C21 1.3900 . ? C21 C22 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C1S Cl3 1.725(11) . ? C1S Cl2 1.730(10) . ? C1S Cl1 1.745(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 C1 Pd1 N3 179.3(3) . . ? C1 Pd1 Br1 88.4(2) . . ? N3 Pd1 Br1 90.97(17) . . ? C1 Pd1 Br2 87.6(2) . . ? N3 Pd1 Br2 93.09(17) . . ? Br1 Pd1 Br2 175.40(4) . . ? C1 N1 C2 109.1(6) . . ? C1 N1 C8 122.7(7) . . ? C2 N1 C8 128.1(6) . . ? C1 N2 C7 109.3(6) . . ? C1 N2 C11 123.0(7) . . ? C7 N2 C11 127.7(6) . . ? C14 N3 N4 106.9(6) . . ? C14 N3 Pd1 128.4(5) . . ? N4 N3 Pd1 123.7(5) . . ? C16 N4 N3 109.7(7) . . ? C16 N4 C19 128.8(7) . . ? N3 N4 C19 121.0(6) . . ? N2 C1 N1 108.8(7) . . ? N2 C1 Pd1 124.3(5) . . ? N1 C1 Pd1 126.9(6) . . ? N1 C2 C7 106.3(6) . . ? N1 C2 C3 132.0(7) . . ? C7 C2 C3 121.7(8) . . ? C2 C3 C4 115.9(8) . . ? C5 C4 C3 121.8(8) . . ? C4 C5 C6 123.1(8) . . ? C5 C6 C7 116.9(8) . . ? N2 C7 C2 106.5(7) . . ? N2 C7 C6 132.8(7) . . ? C2 C7 C6 120.6(8) . . ? N1 C8 C9 109.6(7) . . ? N1 C8 C10 110.8(7) . . ? C9 C8 C10 113.7(7) . . ? N2 C11 C12 111.1(7) . . ? N2 C11 C13 109.4(7) . . ? C12 C11 C13 115.2(8) . . ? N3 C14 C15 108.5(7) . . ? N3 C14 C17 121.1(7) . . ? C15 C14 C17 130.4(8) . . ? C16 C15 C14 108.7(8) . . ? C16 C15 Br3 126.4(7) . . ? C14 C15 Br3 124.9(7) . . ? C15 C16 N4 106.1(7) . . ? C15 C16 C18 132.2(9) . . ? N4 C16 C18 121.6(9) . . ? C20 C19 C24 120.0 . . ? C20 C19 N4 119.8(5) . . ? C24 C19 N4 120.2(5) . . ? C21 C20 C19 120.0 . . ? C20 C21 C22 120.0 . . ? C21 C22 C23 120.0 . . ? C24 C23 C22 120.0 . . ? C23 C24 C19 120.0 . . ? Cl3 C1S Cl2 110.5(6) . . ? Cl3 C1S Cl1 111.5(6) . . ? Cl2 C1S Cl1 110.2(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.544 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.135 data_b223 _database_code_depnum_ccdc_archive 'CCDC 870363' #TrackingRef '- crystallographic data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 Br2 Cl3 I N4 Pd' _chemical_formula_weight 886.00 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' 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' I I -0.4742 1.8119 '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 11.741(2) _cell_length_b 15.964(3) _cell_length_c 16.643(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3119.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 918 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 26.94 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.886 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 4.425 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3925 _exptl_absorpt_correction_T_max 0.5379 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 22662 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7164 _reflns_number_gt 6701 _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^)+(0.0487P)^2^+4.8943P] 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 0.086(10) _refine_ls_number_reflns 7164 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.30126(3) 0.77877(2) 0.76764(2) 0.01351(9) Uani 1 1 d . . . I1 I 0.00048(3) 0.49099(2) 0.63313(2) 0.02230(9) Uani 1 1 d . . . Cl1 Cl 0.79408(16) 0.85324(11) 0.62857(10) 0.0373(4) Uani 1 1 d . . . Cl2 Cl 0.87247(16) 0.71394(12) 0.72381(17) 0.0602(7) Uani 1 1 d . . . Cl3 Cl 0.73422(15) 0.84300(11) 0.79663(10) 0.0340(4) Uani 1 1 d . . . Br1 Br 0.45782(5) 0.74547(4) 0.67995(4) 0.02848(14) Uani 1 1 d . . . Br2 Br 0.15498(5) 0.80945(4) 0.86454(4) 0.02958(14) Uani 1 1 d . . . N1 N 0.4395(4) 0.9243(3) 0.8149(3) 0.0150(9) Uani 1 1 d . . . N2 N 0.4588(4) 0.8217(3) 0.9004(3) 0.0158(9) Uani 1 1 d . . . N3 N 0.1890(4) 0.7071(3) 0.6978(3) 0.0162(9) Uani 1 1 d . . . N4 N 0.1459(4) 0.7324(3) 0.6253(3) 0.0164(9) Uani 1 1 d . . . C1 C 0.4063(5) 0.8455(3) 0.8316(3) 0.0140(10) Uani 1 1 d . . . C2 C 0.5168(4) 0.9523(3) 0.8731(3) 0.0172(10) Uani 1 1 d . . . C3 C 0.5760(5) 1.0271(3) 0.8829(3) 0.0218(12) Uani 1 1 d . . . H3 H 0.5656 1.0728 0.8470 0.026 Uiso 1 1 calc R . . C4 C 0.6504(6) 1.0322(4) 0.9469(4) 0.0264(13) Uani 1 1 d . . . H4 H 0.6928 1.0822 0.9546 0.032 Uiso 1 1 calc R . . C5 C 0.6650(5) 0.9665(4) 1.0002(4) 0.0248(13) Uani 1 1 d . . . H5 H 0.7175 0.9727 1.0433 0.030 Uiso 1 1 calc R . . C6 C 0.6048(5) 0.8909(4) 0.9925(3) 0.0186(11) Uani 1 1 d . . . H6 H 0.6147 0.8459 1.0292 0.022 Uiso 1 1 calc R . . C7 C 0.5285(5) 0.8858(3) 0.9271(3) 0.0163(11) Uani 1 1 d . . . C8 C 0.4006(5) 0.9696(3) 0.7419(3) 0.0197(11) Uani 1 1 d . . . H8 H 0.3479 0.9315 0.7120 0.024 Uiso 1 1 calc R . . C9 C 0.3336(5) 1.0471(4) 0.7650(4) 0.0249(12) Uani 1 1 d . . . H9A H 0.2709 1.0313 0.8007 0.037 Uiso 1 1 calc R . . H9B H 0.3028 1.0735 0.7164 0.037 Uiso 1 1 calc R . . H9C H 0.3839 1.0867 0.7927 0.037 Uiso 1 1 calc R . . C10 C 0.5028(6) 0.9883(4) 0.6865(4) 0.0277(12) Uani 1 1 d . . . H10A H 0.5467 1.0352 0.7085 0.042 Uiso 1 1 calc R . . H10B H 0.4751 1.0030 0.6328 0.042 Uiso 1 1 calc R . . H10C H 0.5516 0.9386 0.6830 0.042 Uiso 1 1 calc R . . C11 C 0.4425(5) 0.7373(3) 0.9371(3) 0.0194(11) Uani 1 1 d . . . H11 H 0.3838 0.7079 0.9040 0.023 Uiso 1 1 calc R . . C12 C 0.3937(5) 0.7453(4) 1.0213(3) 0.0234(12) Uani 1 1 d . . . H12A H 0.4477 0.7755 1.0555 0.035 Uiso 1 1 calc R . . H12B H 0.3803 0.6893 1.0435 0.035 Uiso 1 1 calc R . . H12C H 0.3216 0.7761 1.0191 0.035 Uiso 1 1 calc R . . C13 C 0.5513(5) 0.6865(4) 0.9303(4) 0.0249(12) Uani 1 1 d . . . H13A H 0.5717 0.6802 0.8735 0.037 Uiso 1 1 calc R . . H13B H 0.5395 0.6311 0.9542 0.037 Uiso 1 1 calc R . . H13C H 0.6129 0.7154 0.9587 0.037 Uiso 1 1 calc R . . C14 C 0.0810(5) 0.6715(4) 0.5915(3) 0.0188(11) Uani 1 1 d . . . C15 C 0.0870(5) 0.6037(3) 0.6435(3) 0.0173(11) Uani 1 1 d . . . C16 C 0.1534(5) 0.6290(3) 0.7092(3) 0.0183(11) Uani 1 1 d . . . C17 C 0.1576(5) 0.8180(4) 0.5998(3) 0.0216(12) Uani 1 1 d . . . C18 C 0.1152(5) 0.8817(4) 0.6453(4) 0.0246(13) Uani 1 1 d . . . H18 H 0.0792 0.8699 0.6951 0.030 Uiso 1 1 calc R . . C19 C 0.1244(6) 0.9631(4) 0.6192(5) 0.0337(15) Uani 1 1 d . . . H19 H 0.0961 1.0076 0.6513 0.040 Uiso 1 1 calc R . . C20 C 0.1757(6) 0.9801(4) 0.5451(5) 0.0360(16) Uani 1 1 d . . . H20 H 0.1803 1.0361 0.5263 0.043 Uiso 1 1 calc R . . C21 C 0.2184(6) 0.9178(5) 0.5007(5) 0.0400(18) Uani 1 1 d . . . H21 H 0.2545 0.9301 0.4510 0.048 Uiso 1 1 calc R . . C22 C 0.2104(5) 0.8343(4) 0.5265(4) 0.0275(13) Uani 1 1 d . . . H22 H 0.2403 0.7900 0.4948 0.033 Uiso 1 1 calc R . . C23 C 0.0223(5) 0.6816(4) 0.5137(3) 0.0260(13) Uani 1 1 d . . . H23A H -0.0153 0.7364 0.5119 0.039 Uiso 1 1 calc R . . H23B H -0.0349 0.6373 0.5075 0.039 Uiso 1 1 calc R . . H23C H 0.0779 0.6778 0.4699 0.039 Uiso 1 1 calc R . . C24 C 0.1836(5) 0.5805(4) 0.7824(4) 0.0236(12) Uani 1 1 d . . . H24A H 0.2446 0.6094 0.8115 0.035 Uiso 1 1 calc R . . H24B H 0.2096 0.5244 0.7668 0.035 Uiso 1 1 calc R . . H24C H 0.1165 0.5755 0.8171 0.035 Uiso 1 1 calc R . . C1S C 0.7619(5) 0.7866(4) 0.7096(4) 0.0258(13) Uani 1 1 d . . . H1S H 0.6914 0.7546 0.6955 0.031 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 0.01351(18) 0.01475(17) 0.01229(17) 0.00227(14) -0.00095(15) -0.00115(15) I1 0.01870(17) 0.02170(16) 0.02651(18) -0.00565(14) -0.00288(15) -0.00125(15) Cl1 0.0419(9) 0.0443(9) 0.0256(8) 0.0006(7) 0.0045(7) -0.0050(8) Cl2 0.0370(10) 0.0320(9) 0.1117(19) 0.0226(11) 0.0351(12) 0.0152(8) Cl3 0.0375(9) 0.0403(9) 0.0243(7) -0.0050(6) 0.0041(6) 0.0016(7) Br1 0.0266(3) 0.0309(3) 0.0279(3) -0.0030(2) 0.0038(2) -0.0004(2) Br2 0.0267(3) 0.0333(3) 0.0287(3) 0.0044(3) 0.0057(3) 0.0045(3) N1 0.020(2) 0.014(2) 0.011(2) 0.0004(17) 0.0012(18) -0.0027(17) N2 0.016(2) 0.016(2) 0.016(2) 0.0010(17) 0.0032(18) 0.0030(18) N3 0.013(2) 0.021(2) 0.015(2) -0.0008(17) -0.0013(17) -0.0028(18) N4 0.014(2) 0.025(2) 0.0100(19) 0.0017(18) -0.0031(17) -0.0043(18) C1 0.015(3) 0.014(2) 0.013(2) 0.0038(19) 0.0026(19) 0.002(2) C2 0.016(3) 0.022(2) 0.014(2) -0.001(2) 0.005(2) -0.002(2) C3 0.027(3) 0.017(2) 0.022(3) 0.000(2) 0.007(2) -0.001(2) C4 0.030(3) 0.024(3) 0.025(3) -0.005(2) 0.004(3) -0.009(2) C5 0.028(3) 0.028(3) 0.018(3) -0.003(2) 0.000(2) -0.003(2) C6 0.018(3) 0.026(3) 0.012(3) 0.001(2) -0.003(2) -0.004(2) C7 0.019(3) 0.017(2) 0.014(2) -0.0006(19) 0.000(2) -0.001(2) C8 0.019(3) 0.022(3) 0.018(3) 0.008(2) -0.002(2) 0.002(2) C9 0.023(3) 0.022(3) 0.029(3) 0.001(3) -0.001(3) 0.003(2) C10 0.031(3) 0.030(3) 0.023(3) 0.010(2) 0.007(3) 0.007(3) C11 0.026(3) 0.017(3) 0.016(3) 0.004(2) 0.000(2) -0.002(2) C12 0.016(3) 0.033(3) 0.021(3) 0.009(2) -0.001(2) -0.003(2) C13 0.028(3) 0.022(3) 0.025(3) -0.001(2) -0.005(3) -0.002(2) C14 0.011(2) 0.028(3) 0.017(3) -0.003(2) 0.004(2) -0.001(2) C15 0.012(2) 0.022(3) 0.018(3) 0.003(2) -0.001(2) -0.003(2) C16 0.014(2) 0.022(3) 0.019(3) 0.000(2) 0.001(2) 0.001(2) C17 0.018(3) 0.033(3) 0.014(3) 0.010(2) -0.009(2) -0.003(2) C18 0.016(3) 0.032(3) 0.025(3) 0.009(3) -0.003(2) 0.004(2) C19 0.024(3) 0.030(3) 0.048(4) 0.007(3) -0.007(3) 0.004(3) C20 0.027(4) 0.033(3) 0.049(4) 0.018(3) -0.011(3) -0.006(3) C21 0.028(4) 0.052(4) 0.040(4) 0.021(3) -0.003(3) -0.010(3) C22 0.026(3) 0.038(3) 0.019(3) 0.011(3) 0.003(2) 0.001(3) C23 0.025(3) 0.036(3) 0.017(3) 0.004(2) -0.006(2) -0.006(3) C24 0.023(3) 0.023(3) 0.025(3) 0.004(2) -0.007(2) -0.001(2) C1S 0.020(3) 0.025(3) 0.032(3) -0.005(2) 0.007(2) -0.002(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 C1 1.947(5) . ? Pd1 N3 2.097(4) . ? Pd1 Br2 2.4063(8) . ? Pd1 Br1 2.4066(8) . ? I1 C15 2.073(5) . ? Cl1 C1S 1.759(6) . ? Cl2 C1S 1.757(7) . ? Cl3 C1S 1.736(6) . ? N1 C1 1.346(7) . ? N1 C2 1.400(7) . ? N1 C8 1.485(7) . ? N2 C1 1.355(7) . ? N2 C7 1.383(7) . ? N2 C11 1.491(7) . ? N3 C16 1.329(7) . ? N3 N4 1.369(6) . ? N4 C14 1.357(7) . ? N4 C17 1.438(7) . ? C2 C3 1.392(8) . ? C2 C7 1.398(7) . ? C3 C4 1.380(9) . ? C4 C5 1.385(9) . ? C5 C6 1.404(8) . ? C6 C7 1.413(7) . ? C8 C9 1.516(8) . ? C8 C10 1.542(8) . ? C11 C13 1.517(8) . ? C11 C12 1.519(8) . ? C14 C15 1.389(8) . ? C14 C23 1.476(8) . ? C15 C16 1.403(8) . ? C16 C24 1.486(8) . ? C17 C18 1.361(9) . ? C17 C22 1.393(8) . ? C18 C19 1.374(9) . ? C19 C20 1.398(10) . ? C20 C21 1.337(11) . ? C21 C22 1.403(10) . ? 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 179.5(2) . . ? C1 Pd1 Br2 88.52(16) . . ? N3 Pd1 Br2 91.94(13) . . ? C1 Pd1 Br1 88.21(15) . . ? N3 Pd1 Br1 91.35(12) . . ? Br2 Pd1 Br1 175.25(3) . . ? C1 N1 C2 110.1(4) . . ? C1 N1 C8 122.3(5) . . ? C2 N1 C8 127.5(4) . . ? C1 N2 C7 109.4(4) . . ? C1 N2 C11 122.7(5) . . ? C7 N2 C11 127.8(5) . . ? C16 N3 N4 106.7(4) . . ? C16 N3 Pd1 129.0(4) . . ? N4 N3 Pd1 124.1(3) . . ? C14 N4 N3 111.2(4) . . ? C14 N4 C17 127.7(5) . . ? N3 N4 C17 120.3(4) . . ? N1 C1 N2 107.7(5) . . ? N1 C1 Pd1 125.6(4) . . ? N2 C1 Pd1 126.7(4) . . ? C3 C2 C7 121.9(5) . . ? C3 C2 N1 132.7(5) . . ? C7 C2 N1 105.4(4) . . ? C4 C3 C2 117.2(5) . . ? C3 C4 C5 121.9(6) . . ? C4 C5 C6 122.0(6) . . ? C5 C6 C7 116.1(5) . . ? N2 C7 C2 107.3(5) . . ? N2 C7 C6 131.7(5) . . ? C2 C7 C6 120.9(5) . . ? N1 C8 C9 110.5(5) . . ? N1 C8 C10 110.2(4) . . ? C9 C8 C10 113.4(5) . . ? N2 C11 C13 110.2(5) . . ? N2 C11 C12 110.5(4) . . ? C13 C11 C12 115.6(5) . . ? N4 C14 C15 105.7(5) . . ? N4 C14 C23 123.2(5) . . ? C15 C14 C23 131.0(5) . . ? C14 C15 C16 106.8(5) . . ? C14 C15 I1 126.9(4) . . ? C16 C15 I1 126.0(4) . . ? N3 C16 C15 109.5(5) . . ? N3 C16 C24 122.1(5) . . ? C15 C16 C24 128.4(5) . . ? C18 C17 C22 120.6(6) . . ? C18 C17 N4 120.8(5) . . ? C22 C17 N4 118.6(6) . . ? C17 C18 C19 120.1(6) . . ? C18 C19 C20 119.7(7) . . ? C21 C20 C19 120.3(6) . . ? C20 C21 C22 120.8(7) . . ? C17 C22 C21 118.4(7) . . ? Cl3 C1S Cl2 111.6(4) . . ? Cl3 C1S Cl1 111.5(3) . . ? Cl2 C1S Cl1 110.1(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.342 _refine_diff_density_min -1.000 _refine_diff_density_rms 0.157 data_b176 _database_code_depnum_ccdc_archive 'CCDC 870364' #TrackingRef '- crystallographic data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 Br2 N4 Pd' _chemical_formula_weight 640.74 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 Pbca 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' '-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 9.0480(3) _cell_length_b 16.4781(6) _cell_length_c 35.4180(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5280.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4309 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 22.75 _exptl_crystal_description PLATE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2544 _exptl_absorpt_coefficient_mu 3.747 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2559 _exptl_absorpt_correction_T_max 0.8064 _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 35356 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6056 _reflns_number_gt 4863 _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^)+(0.0500P)^2^+5.4970P] 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 6056 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1314 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 1.199 _refine_ls_restrained_S_all 1.199 _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 0.53507(4) 0.39905(2) 0.124568(11) 0.02290(12) Uani 1 1 d . . . Br1 Br 0.36873(9) 0.34162(4) 0.171242(19) 0.0568(2) Uani 1 1 d . . . Br2 Br 0.71074(7) 0.46400(4) 0.082534(19) 0.0539(2) Uani 1 1 d . . . N1 N 0.6360(4) 0.5091(2) 0.18504(12) 0.0246(9) Uani 1 1 d . . . N2 N 0.4593(4) 0.5630(2) 0.15175(12) 0.0260(9) Uani 1 1 d . . . N3 N 0.5251(5) 0.2959(3) 0.09032(13) 0.0313(10) Uani 1 1 d . . . N4 N 0.4498(5) 0.2967(3) 0.05684(13) 0.0344(11) Uani 1 1 d . . . C1 C 0.5449(5) 0.4962(3) 0.15557(13) 0.0216(10) Uani 1 1 d . . . C2 C 0.6088(6) 0.5851(3) 0.20082(16) 0.0296(12) Uani 1 1 d . . . C3 C 0.6718(7) 0.6260(4) 0.23110(18) 0.0465(16) Uani 1 1 d . . . H3 H 0.7490 0.6032 0.2453 0.056 Uiso 1 1 calc R . . C4 C 0.6150(8) 0.7023(4) 0.2393(2) 0.062(2) Uani 1 1 d . . . H4 H 0.6543 0.7318 0.2597 0.075 Uiso 1 1 calc R . . C5 C 0.5023(8) 0.7359(4) 0.2182(2) 0.062(2) Uani 1 1 d . . . H5 H 0.4667 0.7875 0.2249 0.074 Uiso 1 1 calc R . . C6 C 0.4398(6) 0.6964(3) 0.1877(2) 0.0444(16) Uani 1 1 d . . . H6 H 0.3638 0.7200 0.1734 0.053 Uiso 1 1 calc R . . C7 C 0.4958(5) 0.6193(3) 0.17950(17) 0.0290(12) Uani 1 1 d . . . C8 C 0.7501(6) 0.4495(3) 0.19698(16) 0.0326(12) Uani 1 1 d . . . H8 H 0.7367 0.4007 0.1811 0.039 Uiso 1 1 calc R . . C9 C 0.9016(7) 0.4819(4) 0.1888(2) 0.0575(19) Uani 1 1 d . . . H9A H 0.9067 0.4992 0.1626 0.086 Uiso 1 1 calc R . . H9B H 0.9742 0.4396 0.1932 0.086 Uiso 1 1 calc R . . H9C H 0.9218 0.5277 0.2052 0.086 Uiso 1 1 calc R . . C10 C 0.7261(9) 0.4236(4) 0.23714(19) 0.0603(19) Uani 1 1 d . . . H10A H 0.7508 0.4680 0.2540 0.090 Uiso 1 1 calc R . . H10B H 0.7887 0.3773 0.2427 0.090 Uiso 1 1 calc R . . H10C H 0.6233 0.4086 0.2407 0.090 Uiso 1 1 calc R . . C11 C 0.3440(6) 0.5713(3) 0.12247(18) 0.0383(14) Uani 1 1 d . . . H11 H 0.3412 0.5193 0.1084 0.046 Uiso 1 1 calc R . . C12 C 0.1944(7) 0.5825(5) 0.1398(2) 0.067(2) Uani 1 1 d . . . H12A H 0.1739 0.5376 0.1568 0.100 Uiso 1 1 calc R . . H12B H 0.1202 0.5840 0.1201 0.100 Uiso 1 1 calc R . . H12C H 0.1924 0.6330 0.1538 0.100 Uiso 1 1 calc R . . C13 C 0.3855(9) 0.6367(4) 0.0943(2) 0.069(2) Uani 1 1 d . . . H13A H 0.3966 0.6881 0.1073 0.104 Uiso 1 1 calc R . . H13B H 0.3085 0.6414 0.0754 0.104 Uiso 1 1 calc R . . H13C H 0.4781 0.6225 0.0822 0.104 Uiso 1 1 calc R . . C14 C 0.6084(6) 0.2287(3) 0.08984(18) 0.0389(14) Uani 1 1 d . . . C15 C 0.5829(7) 0.1859(4) 0.05667(19) 0.0454(16) Uani 1 1 d . . . H15 H 0.6264 0.1363 0.0497 0.054 Uiso 1 1 calc R . . C16 C 0.4822(7) 0.2297(4) 0.03604(18) 0.0430(15) Uani 1 1 d . . . C17 C 0.7065(8) 0.2088(4) 0.1220(2) 0.066(2) Uani 1 1 d . . . H17A H 0.7908 0.2452 0.1219 0.099 Uiso 1 1 calc R . . H17B H 0.7405 0.1532 0.1196 0.099 Uiso 1 1 calc R . . H17C H 0.6524 0.2150 0.1454 0.099 Uiso 1 1 calc R . . C18 C 0.4079(10) 0.2138(4) -0.0009(2) 0.069(2) Uani 1 1 d . . . H18A H 0.3024 0.2079 0.0030 0.103 Uiso 1 1 calc R . . H18B H 0.4471 0.1643 -0.0119 0.103 Uiso 1 1 calc R . . H18C H 0.4261 0.2589 -0.0179 0.103 Uiso 1 1 calc R . . C19 C 0.3409(6) 0.3582(3) 0.05048(15) 0.0313(12) Uani 1 1 d . . . C20 C 0.2212(6) 0.3630(3) 0.07442(18) 0.0396(14) Uani 1 1 d . . . H20 H 0.2113 0.3256 0.0943 0.048 Uiso 1 1 calc R . . C21 C 0.1163(7) 0.4222(4) 0.0693(2) 0.0537(18) Uani 1 1 d . . . H21 H 0.0341 0.4254 0.0854 0.064 Uiso 1 1 calc R . . C22 C 0.1324(9) 0.4762(4) 0.0405(2) 0.060(2) Uani 1 1 d . . . H22 H 0.0613 0.5172 0.0372 0.072 Uiso 1 1 calc R . . C23 C 0.2485(10) 0.4723(4) 0.0166(2) 0.060(2) Uani 1 1 d . . . H23 H 0.2568 0.5100 -0.0032 0.072 Uiso 1 1 calc R . . C24 C 0.3557(8) 0.4125(4) 0.02117(18) 0.0489(16) Uani 1 1 d . . . H24 H 0.4366 0.4093 0.0046 0.059 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 0.0255(2) 0.02031(18) 0.0229(2) -0.00217(16) 0.00177(16) 0.00048(15) Br1 0.0793(5) 0.0513(4) 0.0397(4) -0.0014(3) 0.0179(3) -0.0326(4) Br2 0.0476(4) 0.0704(4) 0.0436(4) -0.0057(3) 0.0199(3) -0.0186(3) N1 0.025(2) 0.025(2) 0.023(2) 0.0028(18) -0.0024(18) 0.0002(17) N2 0.023(2) 0.022(2) 0.032(2) -0.0003(18) -0.0020(19) 0.0010(17) N3 0.032(2) 0.032(2) 0.030(3) -0.008(2) -0.003(2) 0.005(2) N4 0.036(3) 0.034(2) 0.033(3) -0.010(2) 0.002(2) 0.003(2) C1 0.022(2) 0.023(2) 0.020(2) -0.0010(19) 0.004(2) -0.0024(19) C2 0.031(3) 0.023(2) 0.035(3) -0.005(2) 0.004(2) -0.004(2) C3 0.051(4) 0.048(3) 0.041(4) -0.011(3) -0.007(3) -0.007(3) C4 0.064(5) 0.058(4) 0.065(5) -0.035(4) -0.010(4) -0.008(4) C5 0.056(4) 0.035(3) 0.094(6) -0.036(4) 0.003(4) 0.002(3) C6 0.034(3) 0.030(3) 0.069(5) -0.013(3) 0.004(3) 0.004(2) C7 0.028(3) 0.018(2) 0.041(3) -0.005(2) 0.007(2) -0.0014(19) C8 0.032(3) 0.031(3) 0.035(3) 0.002(2) -0.004(2) 0.008(2) C9 0.033(3) 0.071(5) 0.069(5) 0.016(4) -0.002(3) 0.001(3) C10 0.079(5) 0.056(4) 0.045(4) 0.018(3) 0.001(4) 0.015(4) C11 0.031(3) 0.030(3) 0.054(4) -0.005(3) -0.015(3) 0.007(2) C12 0.025(3) 0.074(5) 0.102(7) -0.015(5) -0.009(4) 0.005(3) C13 0.077(5) 0.058(4) 0.072(5) 0.033(4) -0.034(4) -0.007(4) C14 0.038(3) 0.033(3) 0.046(4) -0.007(3) -0.001(3) 0.011(3) C15 0.044(3) 0.036(3) 0.056(4) -0.021(3) 0.007(3) 0.010(3) C16 0.046(3) 0.041(3) 0.042(4) -0.019(3) 0.006(3) 0.004(3) C17 0.067(5) 0.050(4) 0.080(6) -0.018(4) -0.027(4) 0.030(4) C18 0.094(6) 0.056(4) 0.056(5) -0.031(4) -0.006(4) 0.010(4) C19 0.035(3) 0.029(3) 0.030(3) -0.008(2) -0.005(2) 0.001(2) C20 0.039(3) 0.036(3) 0.044(4) -0.009(3) -0.001(3) -0.005(3) C21 0.033(3) 0.061(4) 0.067(5) -0.025(4) -0.014(3) 0.010(3) C22 0.066(5) 0.053(4) 0.061(5) -0.018(4) -0.035(4) 0.023(4) C23 0.096(6) 0.044(4) 0.039(4) 0.005(3) -0.026(4) 0.003(4) C24 0.062(4) 0.049(4) 0.036(4) -0.001(3) -0.004(3) -0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 C1 1.943(5) . ? Pd1 N3 2.090(4) . ? Pd1 Br2 2.4266(7) . ? Pd1 Br1 2.4277(7) . ? N1 C1 1.347(6) . ? N1 C2 1.393(6) . ? N1 C8 1.486(6) . ? N2 C1 1.353(6) . ? N2 C7 1.392(7) . ? N2 C11 1.477(7) . ? N3 C14 1.339(6) . ? N3 N4 1.368(6) . ? N4 C16 1.359(7) . ? N4 C19 1.432(7) . ? C2 C3 1.389(8) . ? C2 C7 1.390(8) . ? C3 C4 1.390(9) . ? C4 C5 1.379(10) . ? C5 C6 1.382(10) . ? C6 C7 1.398(7) . ? C8 C9 1.499(8) . ? C8 C10 1.501(8) . ? C11 C12 1.497(9) . ? C11 C13 1.517(9) . ? C14 C15 1.390(8) . ? C14 C17 1.480(9) . ? C15 C16 1.374(9) . ? C16 C18 1.495(9) . ? C19 C24 1.377(8) . ? C19 C20 1.378(8) . ? C20 C21 1.374(8) . ? C21 C22 1.360(10) . ? C22 C23 1.351(11) . ? C23 C24 1.392(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 N3 178.93(19) . . ? C1 Pd1 Br2 87.33(14) . . ? N3 Pd1 Br2 91.76(13) . . ? C1 Pd1 Br1 87.97(14) . . ? N3 Pd1 Br1 92.95(13) . . ? Br2 Pd1 Br1 174.75(3) . . ? C1 N1 C2 110.2(4) . . ? C1 N1 C8 122.7(4) . . ? C2 N1 C8 127.0(4) . . ? C1 N2 C7 109.6(4) . . ? C1 N2 C11 123.4(4) . . ? C7 N2 C11 127.0(4) . . ? C14 N3 N4 106.1(4) . . ? C14 N3 Pd1 131.0(4) . . ? N4 N3 Pd1 121.1(3) . . ? C16 N4 N3 110.8(5) . . ? C16 N4 C19 129.7(5) . . ? N3 N4 C19 119.1(4) . . ? N1 C1 N2 107.4(4) . . ? N1 C1 Pd1 126.6(3) . . ? N2 C1 Pd1 126.0(4) . . ? C3 C2 C7 121.6(5) . . ? C3 C2 N1 132.3(5) . . ? C7 C2 N1 106.0(4) . . ? C2 C3 C4 116.7(6) . . ? C5 C4 C3 121.5(6) . . ? C4 C5 C6 122.5(6) . . ? C5 C6 C7 116.3(6) . . ? C2 C7 N2 106.7(4) . . ? C2 C7 C6 121.4(5) . . ? N2 C7 C6 131.9(5) . . ? N1 C8 C9 110.2(5) . . ? N1 C8 C10 110.9(5) . . ? C9 C8 C10 114.6(6) . . ? N2 C11 C12 111.2(5) . . ? N2 C11 C13 110.6(5) . . ? C12 C11 C13 114.0(6) . . ? N3 C14 C15 109.7(5) . . ? N3 C14 C17 120.7(5) . . ? C15 C14 C17 129.5(5) . . ? C16 C15 C14 107.0(5) . . ? N4 C16 C15 106.4(5) . . ? N4 C16 C18 121.3(6) . . ? C15 C16 C18 132.2(6) . . ? C24 C19 C20 120.2(6) . . ? C24 C19 N4 120.8(5) . . ? C20 C19 N4 119.0(5) . . ? C21 C20 C19 120.1(6) . . ? C22 C21 C20 119.4(7) . . ? C23 C22 C21 121.5(6) . . ? C22 C23 C24 120.1(7) . . ? C19 C24 C23 118.7(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.107 _refine_diff_density_min -1.129 _refine_diff_density_rms 0.131