# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Jan Reedijk' 'Sharief Barends' 'Hans den Dulk' 'Frantisek Hartl' 'Martin Lutz' 'Palanisamy Uma Maheswari' 'Sudeshna Roy' 'A Spek' 'Gilles van Wezel' _publ_contact_author_name 'Jan Reedijk' _publ_contact_author_email REEDIJK@CHEM.LEIDENUNIV.NL _publ_section_title ; DNA cleavage and antitumour activity of platinum(II) and copper(II) compounds derived from 4-methyl-2-N-(2-pyridylmethyl)aminophenol: spectroscopic, electrochemical and biological investigation ; # Attachment 'pt_pyrimol_deposit.cif' data_s3576a _database_code_depnum_ccdc_archive 'CCDC 735958' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 Cl N2 O Pt' _chemical_formula_sum 'C13 H11 Cl N2 O Pt' _chemical_formula_weight 441.78 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' Cl Cl 0.1484 0.1585 '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' Pt Pt -1.7033 8.3905 '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 7.1447(3) _cell_length_b 8.5058(3) _cell_length_c 10.2432(3) _cell_angle_alpha 83.230(2) _cell_angle_beta 76.509(1) _cell_angle_gamma 87.059(2) _cell_volume 600.91(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5835 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 27.49 _exptl_crystal_description needle _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 11.884 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.36 _exptl_absorpt_correction_T_max 0.70 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9030 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2743 _reflns_number_gt 2419 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement Peakref _computing_data_reduction 'EvalCCD, Sadabs' _computing_structure_solution 'DIRDIF-99 (Beurskens et al., 1999)' _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^)+(0.0181P)^2^+0.4300P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2743 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0518 _refine_ls_wR_factor_gt 0.0492 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.28712(2) 0.39569(2) 0.366778(17) 0.02202(7) Uani 1 1 d . . . Cl1 Cl 0.34959(18) 0.31170(15) 0.15497(12) 0.0342(3) Uani 1 1 d . . . O1 O 0.1705(4) 0.1909(4) 0.4633(3) 0.0272(7) Uani 1 1 d . . . N1 N 0.3860(5) 0.6167(4) 0.3162(4) 0.0236(8) Uani 1 1 d . . . N2 N 0.2202(5) 0.4673(4) 0.5458(4) 0.0214(8) Uani 1 1 d . . . C1 C 0.2561(6) 0.6139(5) 0.5520(5) 0.0252(10) Uani 1 1 d . . . H1 H 0.2222 0.6608 0.6343 0.030 Uiso 1 1 calc R . . C11 C 0.3505(6) 0.7018(5) 0.4265(5) 0.0238(10) Uani 1 1 d . . . C12 C 0.4011(6) 0.8576(6) 0.4125(5) 0.0273(10) Uani 1 1 d . . . H12 H 0.3738 0.9161 0.4886 0.033 Uiso 1 1 calc R . . C13 C 0.4926(7) 0.9291(6) 0.2862(5) 0.0340(12) Uani 1 1 d . . . H13 H 0.5287 1.0367 0.2750 0.041 Uiso 1 1 calc R . . C14 C 0.5301(6) 0.8425(6) 0.1781(5) 0.0310(11) Uani 1 1 d . . . H14 H 0.5944 0.8894 0.0916 0.037 Uiso 1 1 calc R . . C15 C 0.4748(6) 0.6878(6) 0.1946(5) 0.0267(10) Uani 1 1 d . . . H15 H 0.4999 0.6296 0.1185 0.032 Uiso 1 1 calc R . . C21 C 0.1286(6) 0.3501(5) 0.6463(4) 0.0221(10) Uani 1 1 d . . . C22 C 0.1075(6) 0.2082(6) 0.5956(4) 0.0232(10) Uani 1 1 d . . . C23 C 0.0169(6) 0.0847(6) 0.6866(5) 0.0269(10) Uani 1 1 d . . . H23 H 0.0021 -0.0143 0.6564 0.032 Uiso 1 1 calc R . . C24 C -0.0510(6) 0.1072(6) 0.8206(5) 0.0301(11) Uani 1 1 d . . . H24 H -0.1141 0.0225 0.8809 0.036 Uiso 1 1 calc R . . C25 C -0.0309(6) 0.2494(6) 0.8718(5) 0.0277(11) Uani 1 1 d . . . C26 C 0.0598(6) 0.3724(6) 0.7816(5) 0.0253(10) Uani 1 1 d . . . H26 H 0.0748 0.4712 0.8122 0.030 Uiso 1 1 calc R . . C27 C -0.1125(7) 0.2733(7) 1.0175(5) 0.0387(13) Uani 1 1 d . . . H27A H -0.1985 0.3670 1.0228 0.058 Uiso 1 1 calc R . . H27B H -0.0073 0.2885 1.0610 0.058 Uiso 1 1 calc R . . H27C H -0.1850 0.1800 1.0636 0.058 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 Pt1 0.02107(10) 0.01881(10) 0.02711(10) -0.00328(7) -0.00675(7) -0.00152(6) Cl1 0.0450(7) 0.0291(7) 0.0283(6) -0.0052(5) -0.0065(5) -0.0016(5) O1 0.0337(18) 0.0187(17) 0.0294(17) -0.0047(14) -0.0051(14) -0.0070(13) N1 0.0207(19) 0.017(2) 0.036(2) -0.0017(17) -0.0115(16) -0.0006(15) N2 0.0194(19) 0.019(2) 0.028(2) -0.0013(16) -0.0088(15) -0.0023(15) C1 0.019(2) 0.023(3) 0.034(3) -0.005(2) -0.0058(19) -0.0007(18) C11 0.018(2) 0.020(2) 0.036(3) -0.008(2) -0.0096(19) -0.0003(17) C12 0.026(2) 0.018(2) 0.041(3) -0.003(2) -0.014(2) -0.0043(19) C13 0.026(3) 0.027(3) 0.052(3) 0.007(2) -0.018(2) -0.003(2) C14 0.023(2) 0.030(3) 0.039(3) 0.007(2) -0.009(2) -0.006(2) C15 0.024(2) 0.026(3) 0.029(2) 0.001(2) -0.0073(19) -0.0035(19) C21 0.018(2) 0.022(2) 0.027(2) -0.0001(19) -0.0087(17) 0.0019(18) C22 0.019(2) 0.026(3) 0.026(2) -0.006(2) -0.0075(18) 0.0019(18) C23 0.025(2) 0.019(2) 0.037(3) -0.004(2) -0.008(2) -0.0018(19) C24 0.020(2) 0.029(3) 0.040(3) 0.000(2) -0.006(2) -0.0029(19) C25 0.025(3) 0.026(3) 0.033(3) -0.003(2) -0.009(2) 0.0001(19) C26 0.022(2) 0.026(3) 0.030(2) -0.009(2) -0.0073(19) 0.0000(19) C27 0.037(3) 0.039(3) 0.037(3) -0.003(3) -0.003(2) -0.003(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 N2 1.946(4) . ? Pt1 N1 2.009(4) . ? Pt1 O1 2.016(3) . ? Pt1 Cl1 2.3017(12) . ? O1 C22 1.347(5) . ? N1 C15 1.346(6) . ? N1 C11 1.381(6) . ? N2 C1 1.298(6) . ? N2 C21 1.412(6) . ? C1 C11 1.444(6) . ? C1 H1 0.9500 . ? C11 C12 1.374(6) . ? C12 C13 1.390(7) . ? C12 H12 0.9500 . ? C13 C14 1.369(7) . ? C13 H13 0.9500 . ? C14 C15 1.373(7) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C21 C26 1.390(6) . ? C21 C22 1.397(6) . ? C22 C23 1.397(6) . ? C23 C24 1.377(6) . ? C23 H23 0.9500 . ? C24 C25 1.400(7) . ? C24 H24 0.9500 . ? C25 C26 1.390(7) . ? C25 C27 1.504(7) . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 N2 Pt1 N1 81.74(15) . . ? N2 Pt1 O1 84.23(14) . . ? N1 Pt1 O1 165.97(14) . . ? N2 Pt1 Cl1 177.04(10) . . ? N1 Pt1 Cl1 99.14(11) . . ? O1 Pt1 Cl1 94.88(9) . . ? C22 O1 Pt1 108.5(3) . . ? C15 N1 C11 118.9(4) . . ? C15 N1 Pt1 129.5(3) . . ? C11 N1 Pt1 111.6(3) . . ? C1 N2 C21 131.1(4) . . ? C1 N2 Pt1 116.0(3) . . ? C21 N2 Pt1 112.7(3) . . ? N2 C1 C11 116.1(4) . . ? N2 C1 H1 121.9 . . ? C11 C1 H1 121.9 . . ? C12 C11 N1 120.7(4) . . ? C12 C11 C1 124.8(4) . . ? N1 C11 C1 114.4(4) . . ? C11 C12 C13 119.5(5) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 119.1(5) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 120.1(5) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? N1 C15 C14 121.6(5) . . ? N1 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C26 C21 C22 122.5(4) . . ? C26 C21 N2 124.4(4) . . ? C22 C21 N2 113.1(4) . . ? O1 C22 C21 121.4(4) . . ? O1 C22 C23 120.9(4) . . ? C21 C22 C23 117.7(4) . . ? C24 C23 C22 119.7(5) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 122.9(5) . . ? C23 C24 H24 118.6 . . ? C25 C24 H24 118.6 . . ? C26 C25 C24 117.6(4) . . ? C26 C25 C27 120.3(5) . . ? C24 C25 C27 122.0(5) . . ? C25 C26 C21 119.6(5) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 N2 Pt1 O1 C22 0.5(3) . . . . ? N1 Pt1 O1 C22 0.7(7) . . . . ? Cl1 Pt1 O1 C22 -176.6(3) . . . . ? N2 Pt1 N1 C15 178.6(4) . . . . ? O1 Pt1 N1 C15 178.5(4) . . . . ? Cl1 Pt1 N1 C15 -4.2(4) . . . . ? N2 Pt1 N1 C11 -2.3(3) . . . . ? O1 Pt1 N1 C11 -2.5(7) . . . . ? Cl1 Pt1 N1 C11 174.8(3) . . . . ? N1 Pt1 N2 C1 3.2(3) . . . . ? O1 Pt1 N2 C1 -176.9(3) . . . . ? N1 Pt1 N2 C21 179.4(3) . . . . ? O1 Pt1 N2 C21 -0.6(3) . . . . ? C21 N2 C1 C11 -178.7(4) . . . . ? Pt1 N2 C1 C11 -3.3(5) . . . . ? C15 N1 C11 C12 1.4(6) . . . . ? Pt1 N1 C11 C12 -177.8(3) . . . . ? C15 N1 C11 C1 -179.5(4) . . . . ? Pt1 N1 C11 C1 1.3(4) . . . . ? N2 C1 C11 C12 -179.7(4) . . . . ? N2 C1 C11 N1 1.2(6) . . . . ? N1 C11 C12 C13 -1.3(7) . . . . ? C1 C11 C12 C13 179.6(4) . . . . ? C11 C12 C13 C14 0.1(7) . . . . ? C12 C13 C14 C15 1.0(7) . . . . ? C11 N1 C15 C14 -0.2(6) . . . . ? Pt1 N1 C15 C14 178.8(3) . . . . ? C13 C14 C15 N1 -1.0(7) . . . . ? C1 N2 C21 C26 -2.0(7) . . . . ? Pt1 N2 C21 C26 -177.6(3) . . . . ? C1 N2 C21 C22 176.1(4) . . . . ? Pt1 N2 C21 C22 0.5(4) . . . . ? Pt1 O1 C22 C21 -0.4(5) . . . . ? Pt1 O1 C22 C23 178.9(3) . . . . ? C26 C21 C22 O1 178.1(4) . . . . ? N2 C21 C22 O1 -0.1(6) . . . . ? C26 C21 C22 C23 -1.3(6) . . . . ? N2 C21 C22 C23 -179.4(4) . . . . ? O1 C22 C23 C24 -178.2(4) . . . . ? C21 C22 C23 C24 1.2(6) . . . . ? C22 C23 C24 C25 -1.0(7) . . . . ? C23 C24 C25 C26 0.8(7) . . . . ? C23 C24 C25 C27 177.7(4) . . . . ? C24 C25 C26 C21 -0.8(6) . . . . ? C27 C25 C26 C21 -177.8(4) . . . . ? C22 C21 C26 C25 1.1(7) . . . . ? N2 C21 C26 C25 179.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.941 _refine_diff_density_min -1.054 _refine_diff_density_rms 0.155 #===END