# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _audit_creation_method SHELXL-97 _publ_section_title ; Unprecedented twofold intramolecular hydroamination in diam(m)ine- dicarboxylatodichloridoplatinum(IV) complexes - ethane-1,2-diamine versus ammine ligands ; loop_ _publ_author_name _publ_author_address 'Michael R. Reithofer' ; Institute of Inorganic Chemistry, University of Vienna Waehringer Str. 42, A-1090 Vienna Austria ; 'Mathea S. Galanski' ; Institute of Inorganic Chemistry, University of Vienna Waehringer Str. 42, A-1090 Vienna Austria ; 'Vladimir B. Arion' ; Institute of Inorganic Chemistry, University of Vienna Waehringer Str. 42, A-1090 Vienna Austria ; 'Bernhard K. Keppler' ; Institute of Inorganic Chemistry, University of Vienna Waehringer Str. 42 A-1090 Vienna Austria ; _publ_contact_author_name 'Mathea S. Galanski' _publ_contact_author_address ; Institute of Inorganic Chemistry University of Vienna Waehringerstr. 42 Vienna 1090 AUSTRIA ; _publ_contact_author_email MATHEA.GALANSKI@UNIVIE.AC.AT # Attachment 'MIRE1042.CIF' data_MIRE104 _database_code_depnum_ccdc_archive 'CCDC 663532' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (OC-6-54)-Amminedichlorido(2R,2S-imino-kappaN-nis[(4-propylamino)- 4-oxobutanoato-2-yl]-kappa^2^O,O')platinum(IV) ; _chemical_name_common ; (OC-6-54)-Amminedichlorido(2R,2S-imino-kappaN-nis((4- propylamino)-4-oxobutanoato-2-yl)-kappa$2!O,O')platinum(IV) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H26.25 Cl2 N4 O6.13 Pt' _chemical_formula_weight 614.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Iba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 22.1412(9) _cell_length_b 22.6423(8) _cell_length_c 8.5427(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4282.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2282 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 30.01 _exptl_crystal_description plate _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.906 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2394 _exptl_absorpt_coefficient_mu 6.839 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1921 _exptl_absorpt_correction_T_max 0.8753 _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61325 _diffrn_reflns_av_R_equivalents 0.0826 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.39 _reflns_number_total 5339 _reflns_number_gt 4259 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0450P)^2^+26.6516P] 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 0.006(11) _refine_ls_number_reflns 5339 _refine_ls_number_parameters 249 _refine_ls_number_restraints 213 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.058 _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 Pt1 Pt 0.845150(10) 0.677872(10) 0.30872(5) 0.01788(8) Uani 1 1 d U . . Cl1 Cl 0.92836(9) 0.62160(10) 0.2391(3) 0.0293(4) Uani 1 1 d U . . Cl2 Cl 0.82290(11) 0.69388(11) 0.0495(2) 0.0317(5) Uani 1 1 d U . . O1 O 0.8974(2) 0.7491(2) 0.3272(11) 0.0271(14) Uani 1 1 d U . . O2 O 0.9674(3) 0.7853(3) 0.4886(8) 0.0438(18) Uani 1 1 d U . . O3 O 0.8410(2) 0.7707(3) 0.7076(7) 0.0242(12) Uani 1 1 d U . . O4 O 0.7955(2) 0.6046(2) 0.3249(11) 0.0323(13) Uani 1 1 d U . . O5 O 0.7882(5) 0.5249(3) 0.4724(9) 0.066(3) Uani 1 1 d U . . O6 O 0.7552(3) 0.6613(2) 0.7021(7) 0.0228(12) Uani 1 1 d U . . N1 N 0.7721(3) 0.7274(3) 0.3643(7) 0.0233(14) Uani 1 1 d U . . H1A H 0.7707 0.7328 0.4698 0.035 Uiso 1 1 calc R . . H1B H 0.7380 0.7085 0.3322 0.035 Uiso 1 1 calc R . . H1C H 0.7747 0.7631 0.3158 0.035 Uiso 1 1 calc R . . N2 N 0.8627(3) 0.6654(3) 0.5398(8) 0.0178(12) Uani 1 1 d U . . H2 H 0.8341 0.6863 0.5971 0.021 Uiso 1 1 calc R . . N3 N 0.9107(3) 0.8019(4) 0.8847(9) 0.0331(17) Uani 1 1 d U . . H3 H 0.9483 0.7985 0.9161 0.040 Uiso 1 1 calc R . . N4 N 0.7348(4) 0.5867(4) 0.8678(9) 0.042(2) Uani 1 1 d U . . H4 H 0.7437 0.5501 0.8939 0.050 Uiso 1 1 calc R . . C1 C 0.9309(4) 0.7468(4) 0.4539(10) 0.0282(17) Uani 1 1 d U . . C2 C 0.9229(3) 0.6932(4) 0.5680(10) 0.0263(16) Uani 1 1 d U . . H2A H 0.9549 0.6634 0.5435 0.032 Uiso 1 1 calc R . . C3 C 0.9331(4) 0.7153(4) 0.7323(11) 0.0312(19) Uani 1 1 d U . . H3A H 0.9754 0.7287 0.7425 0.037 Uiso 1 1 calc R . . H3B H 0.9270 0.6822 0.8065 0.037 Uiso 1 1 calc R . . C4 C 0.8916(3) 0.7654(4) 0.7767(10) 0.030(2) Uani 1 1 d U . . C5 C 0.8742(4) 0.8475(5) 0.9559(12) 0.038(2) Uani 1 1 d U . . H5A H 0.8421 0.8292 1.0204 0.045 Uiso 1 1 calc R . . H5B H 0.8546 0.8715 0.8734 0.045 Uiso 1 1 calc R . . C6 C 0.9132(6) 0.8866(6) 1.0572(18) 0.069(4) Uani 1 1 d U . . H6A H 0.8869 0.9146 1.1142 0.083 Uiso 1 1 calc R . . H6B H 0.9339 0.8617 1.1361 0.083 Uiso 1 1 calc R . . C7 C 0.9590(6) 0.9204(6) 0.971(2) 0.089(5) Uani 1 1 d U . . H7A H 0.9829 0.9440 1.0447 0.133 Uiso 1 1 calc R . . H7B H 0.9391 0.9467 0.8960 0.133 Uiso 1 1 calc R . . H7C H 0.9857 0.8932 0.9146 0.133 Uiso 1 1 calc R . . C8 C 0.8105(5) 0.5744(4) 0.4494(12) 0.039(2) Uani 1 1 d U . . C9 C 0.8527(4) 0.5997(4) 0.5688(11) 0.0312(18) Uani 1 1 d U . . H9 H 0.8925 0.5793 0.5568 0.037 Uiso 1 1 calc R . . C10 C 0.8305(4) 0.5889(4) 0.7365(11) 0.0324(18) Uani 1 1 d U . . H10A H 0.8293 0.5459 0.7566 0.039 Uiso 1 1 calc R . . H10B H 0.8597 0.6067 0.8108 0.039 Uiso 1 1 calc R . . C11 C 0.7697(4) 0.6142(4) 0.7662(8) 0.0255(17) Uani 1 1 d U . . C12 C 0.6817(5) 0.6146(5) 0.9391(13) 0.049(3) Uani 1 1 d U . . H12A H 0.6606 0.6377 0.8574 0.058 Uiso 1 1 calc R . . H12B H 0.6959 0.6429 1.0196 0.058 Uiso 1 1 calc R . . C13 C 0.6367(7) 0.5736(6) 1.0142(15) 0.064(3) Uani 1 1 d U . . H13A H 0.6038 0.5973 1.0616 0.077 Uiso 1 1 calc R . . H13B H 0.6186 0.5482 0.9324 0.077 Uiso 1 1 calc R . . C14 C 0.6633(7) 0.5367(7) 1.1331(16) 0.081(5) Uani 1 1 d U . . H14A H 0.6322 0.5109 1.1777 0.121 Uiso 1 1 calc R . . H14B H 0.6804 0.5616 1.2159 0.121 Uiso 1 1 calc R . . H14C H 0.6953 0.5126 1.0865 0.121 Uiso 1 1 calc R . . O7 O 1.0000(7) 0.5000(7) 0.5557(16) 0.042(8) Uani 0.25 2 d SPR . . 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 Pt1 0.01540(11) 0.02068(12) 0.01756(11) -0.0055(2) -0.0023(2) 0.00392(10) Cl1 0.0247(10) 0.0336(11) 0.0296(10) -0.0103(9) 0.0003(8) 0.0122(9) Cl2 0.0337(11) 0.0448(13) 0.0166(9) -0.0052(9) -0.0032(8) 0.0131(10) O1 0.021(2) 0.030(2) 0.030(4) -0.004(3) 0.010(3) -0.0020(19) O2 0.031(3) 0.044(4) 0.057(4) -0.034(3) 0.013(3) -0.014(3) O3 0.021(3) 0.025(3) 0.026(3) -0.003(2) -0.003(2) 0.006(2) O4 0.032(3) 0.036(3) 0.029(3) -0.018(3) 0.006(3) -0.015(2) O5 0.116(8) 0.031(4) 0.051(5) -0.014(3) 0.024(5) -0.025(4) O6 0.026(3) 0.013(3) 0.030(3) 0.009(2) 0.004(2) 0.004(2) N1 0.015(3) 0.035(4) 0.020(3) -0.005(3) -0.003(2) 0.007(3) N2 0.012(3) 0.021(3) 0.021(3) -0.004(2) 0.002(2) 0.004(2) N3 0.020(4) 0.039(4) 0.041(4) -0.018(3) 0.000(3) 0.001(3) N4 0.068(5) 0.025(4) 0.032(4) 0.010(3) 0.009(4) 0.001(4) C1 0.014(4) 0.039(5) 0.031(4) -0.023(3) 0.010(3) -0.007(3) C2 0.011(3) 0.042(4) 0.026(4) -0.010(3) -0.004(3) 0.008(3) C3 0.018(4) 0.043(5) 0.032(4) -0.011(4) -0.005(3) 0.008(3) C4 0.016(3) 0.038(4) 0.035(7) -0.014(4) -0.003(3) 0.001(3) C5 0.030(5) 0.037(5) 0.046(6) -0.017(4) 0.003(4) 0.003(4) C6 0.068(8) 0.058(8) 0.081(9) -0.043(7) -0.010(7) 0.006(6) C7 0.059(8) 0.053(8) 0.155(16) -0.016(9) -0.025(8) -0.006(6) C8 0.058(6) 0.024(4) 0.035(4) -0.012(3) 0.020(4) -0.012(4) C9 0.051(5) 0.015(3) 0.028(4) 0.004(3) 0.007(3) 0.016(3) C10 0.033(2) 0.032(2) 0.033(2) 0.0017(10) 0.0000(10) 0.0015(10) C11 0.039(4) 0.024(4) 0.014(4) 0.000(3) -0.002(3) 0.006(3) C12 0.038(5) 0.054(7) 0.054(7) 0.034(5) 0.008(4) 0.001(5) C13 0.086(8) 0.061(8) 0.047(7) 0.000(5) 0.012(6) -0.036(7) C14 0.114(13) 0.070(10) 0.058(8) 0.027(7) 0.030(8) -0.006(9) O7 0.019(13) 0.011(13) 0.10(3) 0.000 0.000 0.01(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 Pt1 O1 1.991(5) . ? Pt1 O4 1.995(5) . ? Pt1 N1 2.025(6) . ? Pt1 N2 2.032(7) . ? Pt1 Cl2 2.298(2) . ? Pt1 Cl1 2.3177(19) . ? O1 C1 1.313(12) . ? O2 C1 1.225(10) . ? O3 C4 1.273(9) . ? O4 C8 1.308(13) . ? O5 C8 1.239(11) . ? O6 C11 1.240(9) . ? N2 C2 1.494(10) . ? N2 C9 1.526(10) . ? N3 C4 1.309(10) . ? N3 C5 1.445(11) . ? N4 C11 1.319(10) . ? N4 C12 1.467(13) . ? C1 C2 1.567(13) . ? C2 C3 1.507(12) . ? C3 C4 1.507(12) . ? C5 C6 1.511(15) . ? C6 C7 1.47(2) . ? C8 C9 1.497(14) . ? C9 C10 1.534(13) . ? C10 C11 1.485(12) . ? C12 C13 1.506(15) . ? C13 C14 1.441(19) . ? 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 O1 Pt1 O4 171.2(4) . . ? O1 Pt1 N1 89.8(3) . . ? O4 Pt1 N1 90.2(3) . . ? O1 Pt1 N2 85.7(3) . . ? O4 Pt1 N2 85.6(3) . . ? N1 Pt1 N2 90.1(3) . . ? O1 Pt1 Cl2 94.2(3) . . ? O4 Pt1 Cl2 94.6(3) . . ? N1 Pt1 Cl2 88.13(19) . . ? N2 Pt1 Cl2 178.25(19) . . ? O1 Pt1 Cl1 90.23(15) . . ? O4 Pt1 Cl1 89.93(17) . . ? N1 Pt1 Cl1 178.69(19) . . ? N2 Pt1 Cl1 91.18(18) . . ? Cl2 Pt1 Cl1 90.57(8) . . ? C1 O1 Pt1 111.2(6) . . ? C8 O4 Pt1 110.6(6) . . ? C2 N2 C9 121.0(7) . . ? C2 N2 Pt1 105.6(5) . . ? C9 N2 Pt1 105.4(5) . . ? C4 N3 C5 124.6(8) . . ? C11 N4 C12 122.7(8) . . ? O2 C1 O1 123.0(9) . . ? O2 C1 C2 118.3(8) . . ? O1 C1 C2 118.7(7) . . ? N2 C2 C3 115.0(7) . . ? N2 C2 C1 109.0(6) . . ? C3 C2 C1 107.8(7) . . ? C2 C3 C4 113.2(7) . . ? O3 C4 N3 123.5(8) . . ? O3 C4 C3 119.4(7) . . ? N3 C4 C3 117.2(7) . . ? N3 C5 C6 109.9(8) . . ? C7 C6 C5 114.4(13) . . ? O5 C8 O4 120.1(10) . . ? O5 C8 C9 119.1(10) . . ? O4 C8 C9 120.8(8) . . ? C8 C9 N2 110.7(7) . . ? C8 C9 C10 112.1(8) . . ? N2 C9 C10 110.6(7) . . ? C11 C10 C9 112.9(7) . . ? O6 C11 N4 123.0(8) . . ? O6 C11 C10 119.4(8) . . ? N4 C11 C10 117.5(8) . . ? N4 C12 C13 116.2(10) . . ? C14 C13 C12 112.8(12) . . ? 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 Pt1 O1 C1 107.5(5) . . . . ? N2 Pt1 O1 C1 17.4(5) . . . . ? Cl2 Pt1 O1 C1 -164.3(5) . . . . ? Cl1 Pt1 O1 C1 -73.8(5) . . . . ? N1 Pt1 O4 C8 -108.8(6) . . . . ? N2 Pt1 O4 C8 -18.6(6) . . . . ? Cl2 Pt1 O4 C8 163.1(6) . . . . ? Cl1 Pt1 O4 C8 72.5(6) . . . . ? O1 Pt1 N2 C2 -27.5(5) . . . . ? O4 Pt1 N2 C2 152.5(5) . . . . ? N1 Pt1 N2 C2 -117.3(5) . . . . ? Cl1 Pt1 N2 C2 62.7(4) . . . . ? O1 Pt1 N2 C9 -156.7(5) . . . . ? O4 Pt1 N2 C9 23.3(5) . . . . ? N1 Pt1 N2 C9 113.5(5) . . . . ? Cl1 Pt1 N2 C9 -66.5(5) . . . . ? Pt1 O1 C1 O2 178.7(6) . . . . ? Pt1 O1 C1 C2 -2.6(8) . . . . ? C9 N2 C2 C3 -88.3(9) . . . . ? Pt1 N2 C2 C3 152.4(6) . . . . ? C9 N2 C2 C1 150.6(7) . . . . ? Pt1 N2 C2 C1 31.3(7) . . . . ? O2 C1 C2 N2 158.3(7) . . . . ? O1 C1 C2 N2 -20.5(10) . . . . ? O2 C1 C2 C3 32.8(10) . . . . ? O1 C1 C2 C3 -145.9(7) . . . . ? N2 C2 C3 C4 -64.9(10) . . . . ? C1 C2 C3 C4 56.9(9) . . . . ? C5 N3 C4 O3 9.4(15) . . . . ? C5 N3 C4 C3 -171.6(9) . . . . ? C2 C3 C4 O3 25.2(12) . . . . ? C2 C3 C4 N3 -153.9(8) . . . . ? C4 N3 C5 C6 -171.7(11) . . . . ? N3 C5 C6 C7 64.7(14) . . . . ? Pt1 O4 C8 O5 -173.9(8) . . . . ? Pt1 O4 C8 C9 8.5(11) . . . . ? O5 C8 C9 N2 -166.1(9) . . . . ? O4 C8 C9 N2 11.5(12) . . . . ? O5 C8 C9 C10 -42.0(12) . . . . ? O4 C8 C9 C10 135.6(9) . . . . ? C2 N2 C9 C8 -143.7(8) . . . . ? Pt1 N2 C9 C8 -24.2(8) . . . . ? C2 N2 C9 C10 91.4(9) . . . . ? Pt1 N2 C9 C10 -149.2(6) . . . . ? C8 C9 C10 C11 -58.3(10) . . . . ? N2 C9 C10 C11 65.8(10) . . . . ? C12 N4 C11 O6 -13.1(13) . . . . ? C12 N4 C11 C10 163.0(9) . . . . ? C9 C10 C11 O6 -35.2(12) . . . . ? C9 C10 C11 N4 148.6(8) . . . . ? C11 N4 C12 C13 162.8(10) . . . . ? N4 C12 C13 C14 56.6(15) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.077 _refine_diff_density_min -1.770 _refine_diff_density_rms 0.181