# Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full MedChemComm _journal_coden_cambridge 1476 _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ; ? ; _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # Attachment 'Compound_2.CIF' _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_volume ? _journal_year ? loop_ _publ_author_name _publ_author_address P.Yadav ; School of Chemistry The University of Tasmania, Private Bag 75, Hobart, Tasmania 7001, Australia ; R.Beveridge '' 'J. Blay' '' A.Boyd '' M.Chojnacka '' 'A. Decken' '' A.Deshpande '' 'Michael G. Gardiner' '' T.Hambley '' M.Hughes '' 'L. Jolly' '' J.Lavangie '' T.MacInnis '' S.MacFarland '' E.New '' R.Gossage '' _publ_contact_author_address ; School of Chemistry University of Tasmania Private Bag 75 Hobart Tasmania 7001 Australia ; _publ_contact_author_email michael.gardiner@utas.edu.au _publ_contact_author_fax (+61)_03_6226_2858 _publ_contact_author_phone (+61)_03-6226_2404 _publ_contact_author_name 'Gardiner, M. G.' _publ_contact_letter ; ? #<< contact letter ; _publ_requested_category ? _publ_section_title ; ; data_rg040389 _database_code_depnum_ccdc_archive 'CCDC 800341' #TrackingRef 'Compound_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C5 H12 Cl2 N2 O Pt' _chemical_formula_sum 'C5 H12 Cl2 N2 O Pt' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour Colourless _diffrn_ambient_temperature 173(1) _chemical_formula_weight 382.16 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_int_tables_number 15 _chemical_absolute_configuration ? 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 18.9236(16) _cell_length_b 10.8634(7) _cell_length_c 11.9925(10) _cell_angle_alpha 90.00 _cell_angle_beta 127.540(2) _cell_angle_gamma 90.00 _cell_volume 1954.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 3119 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 28.41 _exptl_crystal_size_max 0.425 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.025 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 14.852 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0602 _exptl_absorpt_correction_T_max 0.6936 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6568 _diffrn_reflns_av_R_equivalents 0.0591 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2194 _reflns_number_gt 1724 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0669P)^2^] 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 2194 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Pt Pt 0.195372(15) -0.003110(16) 0.18025(2) 0.02319(14) Uani 1 1 d . . . Cl1 Cl 0.08072(9) 0.04126(17) -0.05137(14) 0.0333(3) Uani 1 1 d . . . Cl2 Cl 0.26903(10) -0.11616(16) 0.11773(15) 0.0437(4) Uani 1 1 d . . . N1 N 0.2932(3) -0.0413(5) 0.3815(5) 0.0291(10) Uani 1 1 d . . . N2 N 0.1317(3) 0.0914(5) 0.2428(5) 0.0312(11) Uani 1 1 d . . . H2A H 0.1536 0.0676 0.3312 0.047 Uiso 1 1 calc R . . H2B H 0.0722 0.0751 0.1827 0.047 Uiso 1 1 calc R . . H2C H 0.1408 0.1736 0.2422 0.047 Uiso 1 1 calc R . . C2 C 0.3659(6) 0.0178(7) 0.4683(8) 0.046(2) Uani 1 1 d . . . O3 O 0.4225(3) -0.0351(6) 0.5958(5) 0.0561(15) Uani 1 1 d . . . C4 C 0.3782(4) -0.1413(6) 0.5973(6) 0.0521(18) Uani 1 1 d . . . H4A H 0.3663 -0.1309 0.6666 0.063 Uiso 1 1 calc R . . H4B H 0.4149 -0.2161 0.6218 0.063 Uiso 1 1 calc R . . C5 C 0.2911(4) -0.1513(5) 0.4488(6) 0.0369(14) Uani 1 1 d . . . H5A H 0.2896 -0.2269 0.4012 0.044 Uiso 1 1 calc R . . H5B H 0.2390 -0.1508 0.4493 0.044 Uiso 1 1 calc R . . C6 C 0.3953(5) 0.1314(9) 0.4438(8) 0.100(4) Uani 1 1 d . . . H6A H 0.3998 0.1132 0.3675 0.120 Uiso 1 1 calc R . . H6B H 0.3454 0.1903 0.4043 0.120 Uiso 1 1 calc R . . C7 C 0.4679(6) 0.1924(9) 0.5397(12) 0.149(7) Uani 1 1 d . . . H7A H 0.4540 0.2540 0.5834 0.223 Uiso 1 1 calc R . . H7B H 0.4913 0.2336 0.4955 0.223 Uiso 1 1 calc R . . H7C H 0.5128 0.1351 0.6117 0.223 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 Pt 0.0232(2) 0.0275(2) 0.0203(2) -0.00040(7) 0.01399(16) -0.00258(7) Cl1 0.0295(7) 0.0445(9) 0.0222(6) -0.0011(7) 0.0139(6) -0.0009(7) Cl2 0.0520(9) 0.0526(10) 0.0351(7) 0.0089(7) 0.0310(7) 0.0212(7) N1 0.033(3) 0.031(3) 0.024(2) 0.003(2) 0.018(2) -0.003(2) N2 0.036(2) 0.035(3) 0.030(2) -0.003(2) 0.024(2) 0.001(2) C2 0.033(4) 0.064(5) 0.022(3) 0.004(3) 0.006(3) -0.009(3) O3 0.038(3) 0.071(3) 0.026(2) 0.018(3) 0.002(2) -0.006(3) C4 0.054(4) 0.050(4) 0.032(3) 0.009(3) 0.015(3) -0.001(3) C5 0.046(4) 0.031(3) 0.032(3) 0.011(2) 0.023(3) 0.002(3) C6 0.058(5) 0.104(7) 0.048(4) 0.036(5) -0.014(4) -0.050(5) C7 0.049(5) 0.064(7) 0.165(10) 0.047(7) -0.021(6) -0.024(5) _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 Pt N1 1.995(5) . ? Pt N2 2.042(4) . ? Pt Cl2 2.2993(15) . ? Pt Cl1 2.3046(14) . ? N1 C2 1.283(9) . ? N1 C5 1.454(7) . ? N2 H2A 0.9100 . ? N2 H2B 0.9100 . ? N2 H2C 0.9100 . ? C2 O3 1.349(9) . ? C2 C6 1.454(10) . ? O3 C4 1.434(8) . ? C4 C5 1.524(8) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.313(10) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 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 N1 Pt N2 88.9(2) . . ? N1 Pt Cl2 89.06(16) . . ? N2 Pt Cl2 177.36(14) . . ? N1 Pt Cl1 179.02(14) . . ? N2 Pt Cl1 90.26(13) . . ? Cl2 Pt Cl1 91.79(5) . . ? C2 N1 C5 109.9(5) . . ? C2 N1 Pt 128.5(5) . . ? C5 N1 Pt 121.5(4) . . ? Pt N2 H2A 109.5 . . ? Pt N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? Pt N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? N1 C2 O3 115.1(7) . . ? N1 C2 C6 127.9(7) . . ? O3 C2 C6 117.0(7) . . ? C2 O3 C4 106.9(5) . . ? O3 C4 C5 105.4(5) . . ? O3 C4 H4A 110.7 . . ? C5 C4 H4A 110.7 . . ? O3 C4 H4B 110.7 . . ? C5 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? N1 C5 C4 102.4(5) . . ? N1 C5 H5A 111.3 . . ? C4 C5 H5A 111.3 . . ? N1 C5 H5B 111.3 . . ? C4 C5 H5B 111.3 . . ? H5A C5 H5B 109.2 . . ? C7 C6 C2 125.2(8) . . ? C7 C6 H6A 106.0 . . ? C2 C6 H6A 106.0 . . ? C7 C6 H6B 106.0 . . ? C2 C6 H6B 106.0 . . ? H6A C6 H6B 106.3 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 2.709 _refine_diff_density_min -2.530 _refine_diff_density_rms 0.319 #======================================================================= # Data block for single structure (one for each study in the paper) #======================================================================= data_c:\docume~1\mgg\mydocu~1\cad4da~1\090rg3\anal _database_code_depnum_ccdc_archive 'CCDC 800342' #TrackingRef 'Compound_2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 Cl2 N2 O Pt' _chemical_formula_sum 'C11 H14 Cl2 N2 O Pt' _chemical_formula_weight 456.23 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 monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.525(2) _cell_length_b 11.816(3) _cell_length_c 17.129(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.99(4) _cell_angle_gamma 90.00 _cell_volume 1300.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.65 _cell_measurement_theta_max 14.10 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 11.183 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; (see. N.W. Alcock (1970). Cryst. Computing, p271) ; _exptl_absorpt_correction_T_min 0.3126 _exptl_absorpt_correction_T_max 0.4281 _exptl_absorpt_correction_T_ave 0.3732 _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -8 -3 -2 9 2 -1 1 -7 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 14 _diffrn_standards_decay_corr_max 1.512 _diffrn_standards_decay_corr_min 1.000 _diffrn_reflns_number 2446 _diffrn_reflns_av_R_equivalents 0.1140 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2234 _reflns_number_gt 1916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2001) and ORTEPIII (Farrugia, 1997)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; The asymmetric unit contains one discrete molecule. All non-hydrogen atom positions were refined anisotropically. All hydrogens were included in calculated positons with a "riding" model except the N-H hydrogens which were located and positionally refined. 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^)+(0.1031P)^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 2234 _refine_ls_number_parameters 160 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1335 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.05720(5) 0.80210(3) 0.881234(19) 0.0237(2) Uani 1 1 d . . . Cl1 Cl 0.2396(5) 0.9395(3) 0.95862(18) 0.0488(7) Uani 1 1 d . . . Cl2 Cl 0.3435(4) 0.7795(3) 0.81876(17) 0.0375(6) Uani 1 1 d . . . O1 O -0.3504(12) 0.5354(7) 0.8149(4) 0.0405(18) Uani 1 1 d . . . N1 N -0.1199(11) 0.6760(6) 0.8221(4) 0.0195(15) Uani 1 1 d . . . N2 N -0.1898(14) 0.8215(9) 0.9401(6) 0.034(2) Uani 1 1 d D . . C1 C -0.1616(16) 0.6441(9) 0.7357(5) 0.029(2) Uani 1 1 d . . . C2 C -0.2077(18) 0.7478(10) 0.6850(7) 0.041(3) Uani 1 1 d . . . H2A H -0.0818 0.7943 0.6892 0.062 Uiso 1 1 calc R . . H2B H -0.3181 0.7916 0.7031 0.062 Uiso 1 1 calc R . . H2C H -0.2532 0.7252 0.6297 0.062 Uiso 1 1 calc R . . C3 C 0.0259(19) 0.5795(12) 0.7133(7) 0.054(3) Uani 1 1 d . . . H3A H 0.0546 0.5123 0.7469 0.081 Uiso 1 1 calc R . . H3B H 0.1485 0.6289 0.7213 0.081 Uiso 1 1 calc R . . H3C H -0.0063 0.5564 0.6576 0.081 Uiso 1 1 calc R . . C4 C -0.3505(19) 0.5659(11) 0.7333(6) 0.045(3) Uani 1 1 d . . . H4A H -0.4808 0.6058 0.7107 0.054 Uiso 1 1 calc R . . H4B H -0.3369 0.4978 0.7010 0.054 Uiso 1 1 calc R . . C5 C -0.2255(14) 0.6101(8) 0.8593(6) 0.027(2) Uani 1 1 d . . . C6 C -0.2315(15) 0.6135(9) 0.9442(6) 0.029(2) Uani 1 1 d . . . C7 C -0.2188(15) 0.7175(9) 0.9846(6) 0.027(2) Uani 1 1 d . . . C8 C -0.2218(16) 0.7196(12) 1.0648(6) 0.039(3) Uani 1 1 d . . . H8 H -0.2102 0.7894 1.0927 0.047 Uiso 1 1 calc R . . C9 C -0.2421(18) 0.6180(13) 1.1048(6) 0.048(3) Uani 1 1 d . . . H9 H -0.2485 0.6193 1.1598 0.057 Uiso 1 1 calc R . . C10 C -0.2526(16) 0.5182(12) 1.0660(7) 0.045(3) Uani 1 1 d . . . H10 H -0.2595 0.4500 1.0948 0.054 Uiso 1 1 calc R . . C11 C -0.2536(14) 0.5130(10) 0.9851(6) 0.034(2) Uani 1 1 d . . . H11 H -0.2689 0.4426 0.9580 0.041 Uiso 1 1 calc R . . H2AN H -0.311(12) 0.857(10) 0.911(6) 0.041 Uiso 1 1 d D . . H2BN H -0.189(18) 0.884(6) 0.975(6) 0.041 Uiso 1 1 d 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 Pt1 0.0287(3) 0.0204(3) 0.0227(3) -0.00149(12) 0.00590(17) -0.00237(13) Cl1 0.0474(16) 0.0457(17) 0.0551(17) -0.0240(14) 0.0136(13) -0.0189(13) Cl2 0.0344(14) 0.0419(14) 0.0393(14) -0.0014(12) 0.0155(11) -0.0018(11) O1 0.050(4) 0.039(4) 0.034(4) -0.011(3) 0.012(3) -0.013(4) N1 0.021(4) 0.016(3) 0.023(4) -0.007(3) 0.007(3) -0.002(3) N2 0.027(5) 0.042(5) 0.035(5) -0.012(4) 0.010(4) -0.007(4) C1 0.039(5) 0.029(5) 0.018(4) -0.005(4) 0.004(4) -0.002(4) C2 0.044(7) 0.041(7) 0.036(6) 0.014(5) -0.003(5) -0.004(5) C3 0.046(7) 0.065(9) 0.051(7) -0.028(7) 0.010(5) 0.021(6) C4 0.056(7) 0.052(7) 0.029(5) -0.014(5) 0.010(5) -0.022(6) C5 0.022(4) 0.027(5) 0.034(5) -0.004(4) 0.007(4) -0.004(4) C6 0.034(5) 0.029(5) 0.026(5) 0.000(4) 0.012(4) 0.002(4) C7 0.026(5) 0.035(5) 0.021(4) -0.001(4) 0.005(4) 0.000(4) C8 0.025(5) 0.065(8) 0.030(5) -0.011(5) 0.011(4) 0.001(5) C9 0.044(7) 0.079(10) 0.021(5) 0.010(6) 0.010(4) 0.008(6) C10 0.031(5) 0.062(8) 0.043(6) 0.016(6) 0.010(5) 0.000(5) C11 0.022(5) 0.037(6) 0.043(6) 0.005(5) 0.009(4) -0.004(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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 4.5604 (0.0239) x + 8.4063 (0.0436) y + 0.8432 (0.0977) z = 6.8671 (0.0851) * 0.0559 (0.0061) N1 * -0.0951 (0.0067) C1 * 0.1067 (0.0072) C4 * -0.0816 (0.0070) O1 * 0.0142 (0.0062) C5 0.3579 (0.0172) Pt1 Rms deviation of fitted atoms = 0.0780 - 6.3778 (0.0074) x + 1.0302 (0.0505) y - 0.3417 (0.0750) z = 1.7947 (0.0833) Angle to previous plane (with approximate esd) = 40.60 ( 0.39 ) * -0.0090 (0.0068) C6 * 0.0033 (0.0070) C7 * -0.0028 (0.0072) C8 * 0.0083 (0.0076) C9 * -0.0142 (0.0076) C10 * 0.0143 (0.0070) C11 -0.0219 (0.0153) C5 -0.0593 (0.0159) N2 Rms deviation of fitted atoms = 0.0098 1.8044 (0.0154) x - 8.0042 (0.0179) y + 10.6770 (0.0322) z = 3.1264 (0.0377) Angle to previous plane (with approximate esd) = 62.58 ( 0.31 ) * -0.0345 (0.0028) Pt1 * 0.0210 (0.0033) Cl1 * -0.0038 (0.0034) Cl2 * 0.0237 (0.0036) N1 * -0.0064 (0.0041) N2 Rms deviation of fitted atoms = 0.0212 - 6.3349 (0.0122) x + 1.2867 (0.0587) y - 0.7169 (0.1148) z = 1.5911 (0.0964) Angle to previous plane (with approximate esd) = 60.80 ( 0.40 ) * -0.0059 (0.0030) N2 * 0.0121 (0.0061) C7 * -0.0123 (0.0062) C6 * 0.0061 (0.0031) C5 -0.5512 (0.0156) N1 -1.5532 (0.0143) Pt1 Rms deviation of fitted atoms = 0.0096 ; 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 N1 2.043(7) . ? Pt1 N2 2.057(9) . ? Pt1 Cl1 2.294(3) . ? Pt1 Cl2 2.324(3) . ? O1 C5 1.345(12) . ? O1 C4 1.442(13) . ? N1 C5 1.281(12) . ? N1 C1 1.506(11) . ? N2 C7 1.475(14) . ? N2 H2AN 0.96(2) . ? N2 H2BN 0.95(2) . ? C1 C2 1.501(15) . ? C1 C4 1.536(15) . ? C1 C3 1.546(15) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.462(13) . ? C6 C11 1.399(15) . ? C6 C7 1.405(14) . ? C7 C8 1.378(14) . ? C8 C9 1.400(18) . ? C8 H8 0.9500 . ? C9 C10 1.350(19) . ? C9 H9 0.9500 . ? C10 C11 1.386(16) . ? C10 H10 0.9500 . ? C11 H11 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 Pt1 N2 84.3(3) . . ? N1 Pt1 Cl1 174.1(2) . . ? N2 Pt1 Cl1 90.6(3) . . ? N1 Pt1 Cl2 96.8(2) . . ? N2 Pt1 Cl2 178.1(3) . . ? Cl1 Pt1 Cl2 88.26(11) . . ? C5 O1 C4 106.4(8) . . ? C5 N1 C1 108.4(8) . . ? C5 N1 Pt1 120.3(6) . . ? C1 N1 Pt1 131.3(6) . . ? C7 N2 Pt1 110.0(7) . . ? C7 N2 H2AN 118(8) . . ? Pt1 N2 H2AN 116(7) . . ? C7 N2 H2BN 108(7) . . ? Pt1 N2 H2BN 118(7) . . ? H2AN N2 H2BN 84(10) . . ? C2 C1 N1 110.4(8) . . ? C2 C1 C4 113.4(9) . . ? N1 C1 C4 100.6(7) . . ? C2 C1 C3 110.4(10) . . ? N1 C1 C3 110.6(8) . . ? C4 C1 C3 111.2(10) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 C1 105.1(8) . . ? O1 C4 H4A 110.7 . . ? C1 C4 H4A 110.7 . . ? O1 C4 H4B 110.7 . . ? C1 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? N1 C5 O1 116.3(8) . . ? N1 C5 C6 126.0(9) . . ? O1 C5 C6 117.6(8) . . ? C11 C6 C7 119.8(9) . . ? C11 C6 C5 119.8(9) . . ? C7 C6 C5 120.3(9) . . ? C8 C7 C6 119.8(10) . . ? C8 C7 N2 121.6(10) . . ? C6 C7 N2 118.4(8) . . ? C7 C8 C9 119.4(11) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 120.6(10) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 121.5(11) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C6 118.7(11) . . ? C10 C11 H11 120.6 . . ? C6 C11 H11 120.6 . . ? 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 N1 C5 -39.7(8) . . . . ? Cl1 Pt1 N1 C5 -10(3) . . . . ? Cl2 Pt1 N1 C5 138.7(7) . . . . ? N2 Pt1 N1 C1 137.6(8) . . . . ? Cl1 Pt1 N1 C1 167.6(17) . . . . ? Cl2 Pt1 N1 C1 -43.9(8) . . . . ? N1 Pt1 N2 C7 62.6(7) . . . . ? Cl1 Pt1 N2 C7 -114.4(6) . . . . ? Cl2 Pt1 N2 C7 -63(9) . . . . ? C5 N1 C1 C2 132.7(9) . . . . ? Pt1 N1 C1 C2 -44.9(12) . . . . ? C5 N1 C1 C4 12.7(11) . . . . ? Pt1 N1 C1 C4 -164.9(8) . . . . ? C5 N1 C1 C3 -104.9(11) . . . . ? Pt1 N1 C1 C3 77.5(11) . . . . ? C5 O1 C4 C1 16.5(12) . . . . ? C2 C1 C4 O1 -135.0(10) . . . . ? N1 C1 C4 O1 -17.2(11) . . . . ? C3 C1 C4 O1 99.9(11) . . . . ? C1 N1 C5 O1 -3.1(12) . . . . ? Pt1 N1 C5 O1 174.9(6) . . . . ? C1 N1 C5 C6 -179.1(9) . . . . ? Pt1 N1 C5 C6 -1.2(13) . . . . ? C4 O1 C5 N1 -9.0(13) . . . . ? C4 O1 C5 C6 167.4(9) . . . . ? N1 C5 C6 C11 -146.4(10) . . . . ? O1 C5 C6 C11 37.6(13) . . . . ? N1 C5 C6 C7 34.7(15) . . . . ? O1 C5 C6 C7 -141.3(10) . . . . ? C11 C6 C7 C8 2.0(15) . . . . ? C5 C6 C7 C8 -179.1(9) . . . . ? C11 C6 C7 N2 178.3(9) . . . . ? C5 C6 C7 N2 -2.8(14) . . . . ? Pt1 N2 C7 C8 125.1(9) . . . . ? Pt1 N2 C7 C6 -51.2(11) . . . . ? C6 C7 C8 C9 -1.4(15) . . . . ? N2 C7 C8 C9 -177.6(10) . . . . ? C7 C8 C9 C10 1.9(16) . . . . ? C8 C9 C10 C11 -3.1(17) . . . . ? C9 C10 C11 C6 3.6(16) . . . . ? C7 C6 C11 C10 -3.0(14) . . . . ? C5 C6 C11 C10 178.1(9) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 2.076 _refine_diff_density_min -3.273 _refine_diff_density_rms 0.347