# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Zhen-Feng Chen' _publ_contact_author_email CHENZFUBC@YAHOO.COM _publ_section_title ; Potential new inorganic antitumour agents from combining the anticancer traditional Chinese medicine (TCM) liriodenine with metal ions, and DNA binding studies ; loop_ _publ_author_name 'Zhen-Feng Chen.' 'He-Dong Bian.' 'Hoong-Kun Fun.' 'Hong Liang.' ; Yan-Cheng Liu ; 'Li-Min Liu.' 'Hua-Gang Liu.' 'C Orvig' 'San-Hai Qin.' ; Heng-Shan Wang ; 'Bo-Long Wang.' 'Bin Yang.' # Attachment 'ccdc670188.cif' data_lyc010m _database_code_depnum_ccdc_archive 'CCDC 670188' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Cl2 N O6.50 Ru S2' _chemical_formula_weight 630.50 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' S S 0.1246 0.1234 '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' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2751(2) _cell_length_b 22.0127(5) _cell_length_c 12.2893(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.0980(10) _cell_angle_gamma 90.00 _cell_volume 2410.72(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5706 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 30.07 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1276 _exptl_absorpt_coefficient_mu 1.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6366 _exptl_absorpt_correction_T_max 0.8454 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22969 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4260 _reflns_number_gt 3780 _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^)+(0.0333P)^2^+4.4577P] 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 4260 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 Ru1 Ru 0.70685(3) 0.120000(12) 0.66904(2) 0.03328(10) Uani 1 1 d . . . S1 S 0.82419(10) 0.20580(4) 0.64302(8) 0.0447(2) Uani 1 1 d . . . S2 S 0.84981(10) 0.06064(4) 0.59024(8) 0.0439(2) Uani 1 1 d . . . Cl1 Cl 0.87043(11) 0.11200(5) 0.85713(8) 0.0540(3) Uani 1 1 d . . . Cl2 Cl 0.52161(11) 0.12787(4) 0.48955(8) 0.0533(3) Uani 1 1 d . . . O1 O 0.5966(2) 0.04224(10) 0.7060(2) 0.0369(5) Uani 1 1 d . . . O2 O 0.1942(3) 0.06165(15) 1.0586(3) 0.0635(8) Uani 1 1 d . . . O3 O 0.1671(4) 0.16206(18) 1.1017(3) 0.0809(10) Uani 1 1 d . . . O4 O 0.7869(4) 0.26132(13) 0.6958(3) 0.0786(10) Uani 1 1 d . . . O5 O 0.9188(5) 0.08483(15) 0.5040(3) 0.0912(12) Uani 1 1 d . . . N1 N 0.5508(3) 0.15713(12) 0.7473(2) 0.0382(6) Uani 1 1 d . . . C1 C 0.3940(4) 0.12671(16) 0.8676(3) 0.0382(8) Uani 1 1 d . . . C2 C 0.4847(4) 0.11404(14) 0.7954(3) 0.0339(7) Uani 1 1 d . . . C3 C 0.5117(4) 0.05203(15) 0.7680(3) 0.0339(7) Uani 1 1 d . . . C4 C 0.4368(4) 0.00275(15) 0.8095(3) 0.0357(7) Uani 1 1 d . . . C5 C 0.4515(4) -0.05683(16) 0.7744(3) 0.0439(8) Uani 1 1 d . . . H5 H 0.5077 -0.0646 0.7238 0.053 Uiso 1 1 calc R . . C6 C 0.3832(5) -0.10386(18) 0.8144(4) 0.0543(10) Uani 1 1 d . . . H6 H 0.3904 -0.1433 0.7892 0.065 Uiso 1 1 calc R . . C7 C 0.3033(4) -0.09232(19) 0.8926(4) 0.0524(10) Uani 1 1 d . . . H7 H 0.2601 -0.1244 0.9214 0.063 Uiso 1 1 calc R . . C8 C 0.2875(4) -0.03453(18) 0.9275(3) 0.0476(9) Uani 1 1 d . . . H8 H 0.2330 -0.0279 0.9795 0.057 Uiso 1 1 calc R . . C9 C 0.3518(4) 0.01517(16) 0.8864(3) 0.0387(8) Uani 1 1 d . . . C10 C 0.3323(4) 0.07797(17) 0.9179(3) 0.0400(8) Uani 1 1 d . . . C11 C 0.2576(4) 0.0968(2) 0.9946(3) 0.0495(9) Uani 1 1 d . . . C12 C 0.1331(6) 0.1019(3) 1.1270(5) 0.0792(15) Uani 1 1 d . . . H12A H 0.0253 0.0964 1.1097 0.095 Uiso 1 1 calc R . . H12B H 0.1773 0.0933 1.2067 0.095 Uiso 1 1 calc R . . C13 C 0.2424(4) 0.1586(2) 1.0209(4) 0.0574(11) Uani 1 1 d . . . C14 C 0.2935(5) 0.2049(2) 0.9711(4) 0.0607(12) Uani 1 1 d . . . H14 H 0.2782 0.2451 0.9881 0.073 Uiso 1 1 calc R . . C15 C 0.3727(4) 0.18911(17) 0.8908(3) 0.0468(9) Uani 1 1 d . . . C16 C 0.4324(4) 0.23219(17) 0.8319(4) 0.0547(11) Uani 1 1 d . . . H16 H 0.4134 0.2732 0.8400 0.066 Uiso 1 1 calc R . . C17 C 0.5182(4) 0.21532(16) 0.7626(4) 0.0486(9) Uani 1 1 d . . . H17 H 0.5553 0.2454 0.7245 0.058 Uiso 1 1 calc R . . C18 C 0.8065(6) 0.2243(2) 0.4997(4) 0.0717(14) Uani 1 1 d . . . H18A H 0.7034 0.2332 0.4619 0.108 Uiso 1 1 calc R . . H18B H 0.8394 0.1906 0.4632 0.108 Uiso 1 1 calc R . . H18C H 0.8671 0.2593 0.4964 0.108 Uiso 1 1 calc R . . C19 C 1.0239(5) 0.1995(2) 0.6927(5) 0.0725(14) Uani 1 1 d . . . H19A H 1.0688 0.2373 0.6807 0.109 Uiso 1 1 calc R . . H19B H 1.0575 0.1678 0.6519 0.109 Uiso 1 1 calc R . . H19C H 1.0527 0.1901 0.7720 0.109 Uiso 1 1 calc R . . C20 C 0.7406(5) -0.0023(2) 0.5238(4) 0.0679(13) Uani 1 1 d . . . H20A H 0.6572 0.0119 0.4640 0.102 Uiso 1 1 calc R . . H20B H 0.7041 -0.0240 0.5785 0.102 Uiso 1 1 calc R . . H20C H 0.8015 -0.0288 0.4930 0.102 Uiso 1 1 calc R . . C21 C 0.9946(6) 0.0226(3) 0.6891(5) 0.0898(18) Uani 1 1 d . . . H21A H 1.0388 -0.0070 0.6507 0.135 Uiso 1 1 calc R . . H21B H 0.9545 0.0026 0.7437 0.135 Uiso 1 1 calc R . . H21C H 1.0696 0.0513 0.7268 0.135 Uiso 1 1 calc R . . O6 O 0.0139(7) 0.3502(3) 0.8241(5) 0.150(2) Uani 1 1 d . . . O7 O 0.2168(9) 0.1538(4) 0.5300(10) 0.124(3) Uani 0.50 1 d P . . 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 Ru1 0.03626(16) 0.02888(15) 0.03705(17) 0.00000(11) 0.01405(12) -0.00206(11) S1 0.0488(5) 0.0355(5) 0.0541(6) -0.0001(4) 0.0216(4) -0.0080(4) S2 0.0467(5) 0.0370(5) 0.0551(6) -0.0005(4) 0.0259(4) 0.0004(4) Cl1 0.0509(5) 0.0691(7) 0.0407(5) 0.0056(4) 0.0106(4) -0.0030(5) Cl2 0.0554(5) 0.0488(5) 0.0483(6) 0.0032(4) 0.0021(4) -0.0026(4) O1 0.0430(12) 0.0302(12) 0.0430(14) -0.0011(10) 0.0209(11) -0.0014(10) O2 0.0582(17) 0.085(2) 0.0587(18) 0.0080(16) 0.0356(15) 0.0036(15) O3 0.086(2) 0.098(3) 0.078(2) -0.019(2) 0.055(2) 0.006(2) O4 0.089(2) 0.0432(17) 0.124(3) -0.0183(18) 0.065(2) -0.0165(16) O5 0.133(3) 0.055(2) 0.124(3) -0.001(2) 0.100(3) -0.002(2) N1 0.0386(15) 0.0343(15) 0.0439(17) -0.0054(13) 0.0150(13) -0.0037(12) C1 0.0329(16) 0.043(2) 0.0396(19) -0.0077(15) 0.0111(14) -0.0012(14) C2 0.0331(16) 0.0322(17) 0.0366(18) -0.0032(14) 0.0097(14) -0.0031(13) C3 0.0337(16) 0.0364(18) 0.0318(17) -0.0007(14) 0.0091(14) -0.0007(14) C4 0.0335(16) 0.0346(18) 0.0370(18) 0.0038(14) 0.0066(14) -0.0041(13) C5 0.0450(19) 0.0373(19) 0.050(2) 0.0012(16) 0.0151(17) -0.0013(15) C6 0.057(2) 0.036(2) 0.071(3) 0.0021(19) 0.019(2) -0.0056(17) C7 0.048(2) 0.048(2) 0.063(3) 0.015(2) 0.0173(19) -0.0083(18) C8 0.0408(19) 0.057(2) 0.048(2) 0.0079(18) 0.0165(17) -0.0070(17) C9 0.0311(16) 0.048(2) 0.0361(19) 0.0032(15) 0.0074(14) -0.0031(14) C10 0.0310(16) 0.051(2) 0.0383(19) -0.0025(16) 0.0103(15) -0.0032(15) C11 0.0401(19) 0.067(3) 0.044(2) -0.0041(19) 0.0162(17) -0.0007(18) C12 0.073(3) 0.114(5) 0.067(3) -0.003(3) 0.045(3) 0.012(3) C13 0.049(2) 0.075(3) 0.055(3) -0.016(2) 0.026(2) 0.003(2) C14 0.055(2) 0.061(3) 0.072(3) -0.027(2) 0.029(2) 0.000(2) C15 0.0407(19) 0.046(2) 0.055(2) -0.0150(18) 0.0166(17) -0.0019(16) C16 0.051(2) 0.036(2) 0.080(3) -0.020(2) 0.025(2) -0.0038(17) C17 0.052(2) 0.0313(18) 0.068(3) -0.0061(18) 0.024(2) -0.0041(16) C18 0.079(3) 0.073(3) 0.064(3) 0.026(2) 0.020(2) -0.015(3) C19 0.051(2) 0.073(3) 0.090(4) 0.010(3) 0.012(2) -0.023(2) C20 0.069(3) 0.056(3) 0.083(3) -0.024(2) 0.026(3) -0.002(2) C21 0.078(3) 0.087(4) 0.092(4) -0.017(3) 0.001(3) 0.037(3) O6 0.204(6) 0.134(4) 0.153(5) -0.044(4) 0.120(5) -0.066(4) O7 0.088(6) 0.088(6) 0.215(11) -0.030(6) 0.076(7) -0.005(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 Ru1 O1 2.107(2) . ? Ru1 N1 2.112(3) . ? Ru1 S1 2.2466(9) . ? Ru1 S2 2.2617(9) . ? Ru1 Cl1 2.3940(10) . ? Ru1 Cl2 2.3971(10) . ? S1 O4 1.469(3) . ? S1 C18 1.770(4) . ? S1 C19 1.788(4) . ? S2 O5 1.481(3) . ? S2 C21 1.754(5) . ? S2 C20 1.776(4) . ? O1 C3 1.256(4) . ? O2 C11 1.348(5) . ? O2 C12 1.440(5) . ? O3 C13 1.365(5) . ? O3 C12 1.416(7) . ? N1 C17 1.341(4) . ? N1 C2 1.351(4) . ? C1 C2 1.409(5) . ? C1 C15 1.428(5) . ? C1 C10 1.434(5) . ? C2 C3 1.444(4) . ? C3 C4 1.455(5) . ? C4 C5 1.399(5) . ? C4 C9 1.415(5) . ? C5 C6 1.374(5) . ? C5 H5 0.9300 . ? C6 C7 1.390(6) . ? C6 H6 0.9300 . ? C7 C8 1.363(6) . ? C7 H7 0.9300 . ? C8 C9 1.405(5) . ? C8 H8 0.9300 . ? C9 C10 1.460(5) . ? C10 C11 1.379(5) . ? C11 C13 1.415(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.340(6) . ? C14 C15 1.427(5) . ? C14 H14 0.9300 . ? C15 C16 1.397(6) . ? C16 C17 1.369(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 Ru1 N1 77.36(9) . . ? O1 Ru1 S1 175.47(7) . . ? N1 Ru1 S1 99.19(8) . . ? O1 Ru1 S2 90.02(6) . . ? N1 Ru1 S2 167.37(8) . . ? S1 Ru1 S2 93.44(3) . . ? O1 Ru1 Cl1 86.98(7) . . ? N1 Ru1 Cl1 85.40(8) . . ? S1 Ru1 Cl1 89.83(4) . . ? S2 Ru1 Cl1 94.65(4) . . ? O1 Ru1 Cl2 89.45(7) . . ? N1 Ru1 Cl2 89.09(8) . . ? S1 Ru1 Cl2 93.45(4) . . ? S2 Ru1 Cl2 90.20(4) . . ? Cl1 Ru1 Cl2 173.98(4) . . ? O4 S1 C18 106.2(2) . . ? O4 S1 C19 105.2(2) . . ? C18 S1 C19 99.1(2) . . ? O4 S1 Ru1 116.97(13) . . ? C18 S1 Ru1 114.86(17) . . ? C19 S1 Ru1 112.55(16) . . ? O5 S2 C21 105.5(3) . . ? O5 S2 C20 104.8(2) . . ? C21 S2 C20 100.1(3) . . ? O5 S2 Ru1 121.32(14) . . ? C21 S2 Ru1 113.99(19) . . ? C20 S2 Ru1 108.68(15) . . ? C3 O1 Ru1 114.5(2) . . ? C11 O2 C12 107.1(4) . . ? C13 O3 C12 107.3(4) . . ? C17 N1 C2 117.5(3) . . ? C17 N1 Ru1 130.0(2) . . ? C2 N1 Ru1 112.3(2) . . ? C2 C1 C15 117.1(3) . . ? C2 C1 C10 120.2(3) . . ? C15 C1 C10 122.7(3) . . ? N1 C2 C1 124.0(3) . . ? N1 C2 C3 115.6(3) . . ? C1 C2 C3 120.4(3) . . ? O1 C3 C2 118.8(3) . . ? O1 C3 C4 121.7(3) . . ? C2 C3 C4 119.5(3) . . ? C5 C4 C9 120.5(3) . . ? C5 C4 C3 119.6(3) . . ? C9 C4 C3 119.9(3) . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 119.8(4) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 120.8(4) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 121.3(4) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 117.4(3) . . ? C8 C9 C10 123.1(3) . . ? C4 C9 C10 119.5(3) . . ? C11 C10 C1 114.0(3) . . ? C11 C10 C9 126.0(3) . . ? C1 C10 C9 120.0(3) . . ? O2 C11 C10 127.6(4) . . ? O2 C11 C13 109.3(3) . . ? C10 C11 C13 123.1(4) . . ? O3 C12 O2 107.4(4) . . ? O3 C12 H12A 110.2 . . ? O2 C12 H12A 110.2 . . ? O3 C12 H12B 110.2 . . ? O2 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? C14 C13 O3 127.3(4) . . ? C14 C13 C11 123.8(4) . . ? O3 C13 C11 108.9(4) . . ? C13 C14 C15 116.5(4) . . ? C13 C14 H14 121.8 . . ? C15 C14 H14 121.8 . . ? C16 C15 C14 123.2(4) . . ? C16 C15 C1 116.9(3) . . ? C14 C15 C1 119.9(4) . . ? C17 C16 C15 121.4(3) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? N1 C17 C16 122.6(4) . . ? N1 C17 H17 118.7 . . ? C16 C17 H17 118.7 . . ? S1 C18 H18A 109.5 . . ? S1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? S1 C19 H19A 109.5 . . ? S1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? S1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? S2 C20 H20A 109.5 . . ? S2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? S2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? S2 C21 H21A 109.5 . . ? S2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? S2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 N1 Ru1 S1 O4 8.3(2) . . . . ? S2 Ru1 S1 O4 -171.68(19) . . . . ? Cl1 Ru1 S1 O4 -77.03(19) . . . . ? Cl2 Ru1 S1 O4 97.92(19) . . . . ? N1 Ru1 S1 C18 -117.3(2) . . . . ? S2 Ru1 S1 C18 62.8(2) . . . . ? Cl1 Ru1 S1 C18 157.4(2) . . . . ? Cl2 Ru1 S1 C18 -27.6(2) . . . . ? N1 Ru1 S1 C19 130.3(2) . . . . ? S2 Ru1 S1 C19 -49.7(2) . . . . ? Cl1 Ru1 S1 C19 45.0(2) . . . . ? Cl2 Ru1 S1 C19 -140.1(2) . . . . ? O1 Ru1 S2 O5 155.6(2) . . . . ? N1 Ru1 S2 O5 152.9(4) . . . . ? S1 Ru1 S2 O5 -27.3(2) . . . . ? Cl1 Ru1 S2 O5 -117.4(2) . . . . ? Cl2 Ru1 S2 O5 66.2(2) . . . . ? O1 Ru1 S2 C21 -76.5(2) . . . . ? N1 Ru1 S2 C21 -79.2(4) . . . . ? S1 Ru1 S2 C21 100.6(2) . . . . ? Cl1 Ru1 S2 C21 10.5(2) . . . . ? Cl2 Ru1 S2 C21 -165.9(2) . . . . ? O1 Ru1 S2 C20 34.2(2) . . . . ? N1 Ru1 S2 C20 31.5(4) . . . . ? S1 Ru1 S2 C20 -148.74(19) . . . . ? Cl1 Ru1 S2 C20 121.15(19) . . . . ? Cl2 Ru1 S2 C20 -55.28(19) . . . . ? N1 Ru1 O1 C3 -9.6(2) . . . . ? S2 Ru1 O1 C3 171.0(2) . . . . ? Cl1 Ru1 O1 C3 76.3(2) . . . . ? Cl2 Ru1 O1 C3 -98.8(2) . . . . ? O1 Ru1 N1 C17 -175.0(3) . . . . ? S1 Ru1 N1 C17 8.0(3) . . . . ? S2 Ru1 N1 C17 -172.2(3) . . . . ? Cl1 Ru1 N1 C17 97.1(3) . . . . ? Cl2 Ru1 N1 C17 -85.4(3) . . . . ? O1 Ru1 N1 C2 10.5(2) . . . . ? S1 Ru1 N1 C2 -166.5(2) . . . . ? S2 Ru1 N1 C2 13.3(5) . . . . ? Cl1 Ru1 N1 C2 -77.4(2) . . . . ? Cl2 Ru1 N1 C2 100.1(2) . . . . ? C17 N1 C2 C1 -5.4(5) . . . . ? Ru1 N1 C2 C1 169.9(3) . . . . ? C17 N1 C2 C3 174.4(3) . . . . ? Ru1 N1 C2 C3 -10.4(4) . . . . ? C15 C1 C2 N1 -0.4(5) . . . . ? C10 C1 C2 N1 -177.9(3) . . . . ? C15 C1 C2 C3 179.9(3) . . . . ? C10 C1 C2 C3 2.4(5) . . . . ? Ru1 O1 C3 C2 7.2(4) . . . . ? Ru1 O1 C3 C4 -174.8(2) . . . . ? N1 C2 C3 O1 2.3(4) . . . . ? C1 C2 C3 O1 -177.9(3) . . . . ? N1 C2 C3 C4 -175.8(3) . . . . ? C1 C2 C3 C4 4.0(5) . . . . ? O1 C3 C4 C5 -4.1(5) . . . . ? C2 C3 C4 C5 174.0(3) . . . . ? O1 C3 C4 C9 174.9(3) . . . . ? C2 C3 C4 C9 -7.1(5) . . . . ? C9 C4 C5 C6 0.1(5) . . . . ? C3 C4 C5 C6 179.0(3) . . . . ? C4 C5 C6 C7 -2.0(6) . . . . ? C5 C6 C7 C8 2.2(6) . . . . ? C6 C7 C8 C9 -0.4(6) . . . . ? C7 C8 C9 C4 -1.5(5) . . . . ? C7 C8 C9 C10 177.3(3) . . . . ? C5 C4 C9 C8 1.7(5) . . . . ? C3 C4 C9 C8 -177.3(3) . . . . ? C5 C4 C9 C10 -177.2(3) . . . . ? C3 C4 C9 C10 3.9(5) . . . . ? C2 C1 C10 C11 174.3(3) . . . . ? C15 C1 C10 C11 -3.1(5) . . . . ? C2 C1 C10 C9 -5.6(5) . . . . ? C15 C1 C10 C9 177.0(3) . . . . ? C8 C9 C10 C11 3.7(6) . . . . ? C4 C9 C10 C11 -177.4(3) . . . . ? C8 C9 C10 C1 -176.4(3) . . . . ? C4 C9 C10 C1 2.5(5) . . . . ? C12 O2 C11 C10 178.7(4) . . . . ? C12 O2 C11 C13 1.2(5) . . . . ? C1 C10 C11 O2 -176.8(3) . . . . ? C9 C10 C11 O2 3.1(6) . . . . ? C1 C10 C11 C13 0.4(5) . . . . ? C9 C10 C11 C13 -179.7(4) . . . . ? C13 O3 C12 O2 1.0(5) . . . . ? C11 O2 C12 O3 -1.4(5) . . . . ? C12 O3 C13 C14 178.8(5) . . . . ? C12 O3 C13 C11 -0.3(5) . . . . ? O2 C11 C13 C14 -179.7(4) . . . . ? C10 C11 C13 C14 2.6(7) . . . . ? O2 C11 C13 O3 -0.6(5) . . . . ? C10 C11 C13 O3 -178.2(4) . . . . ? O3 C13 C14 C15 178.4(4) . . . . ? C11 C13 C14 C15 -2.7(6) . . . . ? C13 C14 C15 C16 179.8(4) . . . . ? C13 C14 C15 C1 -0.1(6) . . . . ? C2 C1 C15 C16 5.7(5) . . . . ? C10 C1 C15 C16 -176.9(3) . . . . ? C2 C1 C15 C14 -174.4(3) . . . . ? C10 C1 C15 C14 3.1(5) . . . . ? C14 C15 C16 C17 174.6(4) . . . . ? C1 C15 C16 C17 -5.5(6) . . . . ? C2 N1 C17 C16 5.8(5) . . . . ? Ru1 N1 C17 C16 -168.5(3) . . . . ? C15 C16 C17 N1 -0.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.877 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.067 # Attachment 'ccdc670189.cif' data_lyc017m _database_code_depnum_ccdc_archive 'CCDC 670189' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 Cl2 N O4 Pt S' _chemical_formula_weight 619.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' S S 0.1246 0.1234 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4271(2) _cell_length_b 10.7087(3) _cell_length_c 11.8244(5) _cell_angle_alpha 109.749(2) _cell_angle_beta 102.533(2) _cell_angle_gamma 100.9460(10) _cell_volume 939.28(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5634 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 25.04 _exptl_crystal_description Rhombohedral _exptl_crystal_colour brown _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 7.892 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2709 _exptl_absorpt_correction_T_max 0.6199 _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 'CCD area detector' _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 11731 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3312 _reflns_number_gt 3023 _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^)+(0.0220P)^2^+3.6793P] 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 3312 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0602 _refine_ls_wR_factor_gt 0.0583 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.24512(3) 0.22240(2) 0.482895(19) 0.01616(8) Uani 1 1 d . . . S1 S 0.50372(17) 0.21476(13) 0.47846(12) 0.0173(3) Uani 1 1 d . . . Cl1 Cl -0.02451(17) 0.23618(13) 0.48608(12) 0.0205(3) Uani 1 1 d . . . Cl2 Cl 0.35691(17) 0.39443(13) 0.68280(12) 0.0219(3) Uani 1 1 d . . . N1 N 0.1344(5) 0.0551(4) 0.3118(4) 0.0140(9) Uani 1 1 d . . . O1 O -0.0221(5) -0.4644(4) -0.1995(3) 0.0224(8) Uani 1 1 d . . . O2 O 0.1464(5) -0.2782(4) -0.2151(3) 0.0187(8) Uani 1 1 d . . . O3 O 0.2752(5) 0.2841(4) 0.2688(3) 0.0181(8) Uani 1 1 d . . . O4 O 0.5141(5) 0.1052(4) 0.3687(3) 0.0196(8) Uani 1 1 d . . . C1 C 0.0354(7) -0.0563(5) 0.3190(5) 0.0187(11) Uani 1 1 d . . . H1A H 0.0080 -0.0452 0.3932 0.022 Uiso 1 1 calc R . . C2 C -0.0259(7) -0.1842(5) 0.2218(5) 0.0189(11) Uani 1 1 d . . . H2A H -0.0954 -0.2570 0.2302 0.023 Uiso 1 1 calc R . . C3 C 0.0156(6) -0.2057(5) 0.1100(5) 0.0145(10) Uani 1 1 d . . . C4 C -0.0389(7) -0.3385(5) 0.0098(5) 0.0180(11) Uani 1 1 d . . . H4A H -0.1055 -0.4151 0.0151 0.022 Uiso 1 1 calc R . . C5 C 0.0106(7) -0.3486(5) -0.0937(5) 0.0161(11) Uani 1 1 d . . . C6 C 0.0415(8) -0.4168(5) -0.2868(5) 0.0230(12) Uani 1 1 d . . . H6A H 0.1065 -0.4750 -0.3252 0.028 Uiso 1 1 calc R . . H6B H -0.0519 -0.4197 -0.3531 0.028 Uiso 1 1 calc R . . C7 C 0.1122(6) -0.2339(5) -0.1029(4) 0.0147(10) Uani 1 1 d . . . C8 C 0.1667(6) -0.1015(5) -0.0118(5) 0.0148(10) Uani 1 1 d . . . C9 C 0.2722(6) 0.0188(5) -0.0198(5) 0.0159(10) Uani 1 1 d . . . C10 C 0.3290(7) 0.0104(5) -0.1252(5) 0.0188(11) Uani 1 1 d . . . H10A H 0.3007 -0.0745 -0.1926 0.023 Uiso 1 1 calc R . . C11 C 0.4263(7) 0.1275(6) -0.1290(5) 0.0227(12) Uani 1 1 d . . . H11A H 0.4631 0.1202 -0.1990 0.027 Uiso 1 1 calc R . . C12 C 0.4698(7) 0.2554(6) -0.0302(5) 0.0224(12) Uani 1 1 d . . . H12A H 0.5347 0.3335 -0.0343 0.027 Uiso 1 1 calc R . . C13 C 0.4162(7) 0.2664(5) 0.0743(5) 0.0190(11) Uani 1 1 d . . . H13A H 0.4468 0.3518 0.1415 0.023 Uiso 1 1 calc R . . C14 C 0.3156(6) 0.1486(5) 0.0794(5) 0.0153(10) Uani 1 1 d . . . C15 C 0.2573(6) 0.1674(5) 0.1902(5) 0.0148(10) Uani 1 1 d . . . C16 C 0.1682(6) 0.0398(5) 0.2020(5) 0.0148(10) Uani 1 1 d . . . C17 C 0.1174(6) -0.0884(5) 0.1004(4) 0.0127(10) Uani 1 1 d . . . C18 C 0.6238(7) 0.2036(6) 0.6167(5) 0.0243(12) Uani 1 1 d . . . H18A H 0.5716 0.1184 0.6214 0.036 Uiso 1 1 calc R . . H18B H 0.6273 0.2802 0.6898 0.036 Uiso 1 1 calc R . . H18C H 0.7372 0.2062 0.6135 0.036 Uiso 1 1 calc R . . C19 C 0.6241(7) 0.3761(5) 0.4893(5) 0.0224(12) Uani 1 1 d . . . H19A H 0.7368 0.3723 0.4887 0.034 Uiso 1 1 calc R . . H19B H 0.6295 0.4484 0.5663 0.034 Uiso 1 1 calc R . . H19C H 0.5710 0.3949 0.4188 0.034 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 0.01907(12) 0.01367(11) 0.01562(11) 0.00470(8) 0.00724(8) 0.00422(8) S1 0.0201(7) 0.0145(6) 0.0182(6) 0.0059(5) 0.0081(5) 0.0055(5) Cl1 0.0223(7) 0.0218(7) 0.0215(6) 0.0082(5) 0.0117(5) 0.0102(5) Cl2 0.0253(7) 0.0168(6) 0.0190(6) 0.0016(5) 0.0084(5) 0.0042(5) N1 0.019(2) 0.008(2) 0.016(2) 0.0018(17) 0.0092(18) 0.0064(17) O1 0.037(2) 0.0112(18) 0.0189(19) 0.0034(16) 0.0129(17) 0.0059(17) O2 0.023(2) 0.0139(18) 0.0151(17) 0.0008(15) 0.0078(15) 0.0027(15) O3 0.022(2) 0.0154(19) 0.0173(18) 0.0045(16) 0.0089(15) 0.0056(15) O4 0.023(2) 0.0147(19) 0.0191(18) 0.0035(15) 0.0067(16) 0.0073(16) C1 0.022(3) 0.021(3) 0.015(3) 0.007(2) 0.009(2) 0.007(2) C2 0.021(3) 0.017(3) 0.023(3) 0.010(2) 0.009(2) 0.008(2) C3 0.018(3) 0.013(3) 0.014(2) 0.006(2) 0.004(2) 0.008(2) C4 0.017(3) 0.015(3) 0.022(3) 0.008(2) 0.004(2) 0.005(2) C5 0.022(3) 0.008(2) 0.016(2) 0.003(2) 0.004(2) 0.006(2) C6 0.036(3) 0.012(3) 0.019(3) 0.003(2) 0.011(2) 0.007(2) C7 0.018(3) 0.015(3) 0.013(2) 0.003(2) 0.005(2) 0.010(2) C8 0.014(3) 0.018(3) 0.017(2) 0.009(2) 0.006(2) 0.011(2) C9 0.015(3) 0.016(3) 0.018(2) 0.007(2) 0.005(2) 0.007(2) C10 0.020(3) 0.015(3) 0.019(3) 0.002(2) 0.007(2) 0.007(2) C11 0.027(3) 0.022(3) 0.022(3) 0.008(2) 0.014(2) 0.008(2) C12 0.021(3) 0.017(3) 0.030(3) 0.010(2) 0.014(2) 0.001(2) C13 0.020(3) 0.015(3) 0.020(3) 0.003(2) 0.005(2) 0.006(2) C14 0.015(3) 0.017(3) 0.015(2) 0.006(2) 0.003(2) 0.007(2) C15 0.013(2) 0.015(3) 0.015(2) 0.005(2) 0.002(2) 0.006(2) C16 0.017(3) 0.014(3) 0.014(2) 0.005(2) 0.004(2) 0.007(2) C17 0.013(2) 0.012(2) 0.013(2) 0.004(2) 0.004(2) 0.006(2) C18 0.026(3) 0.023(3) 0.024(3) 0.010(2) 0.008(2) 0.008(2) C19 0.020(3) 0.017(3) 0.031(3) 0.011(2) 0.009(2) 0.005(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 N1 2.066(4) . ? Pt1 S1 2.2075(13) . ? Pt1 Cl2 2.3022(13) . ? Pt1 Cl1 2.3124(13) . ? Pt1 O3 2.873(3) . ? S1 O4 1.459(4) . ? S1 C19 1.778(5) . ? S1 C18 1.780(5) . ? N1 C16 1.353(6) . ? N1 C1 1.359(7) . ? O1 C5 1.361(6) . ? O1 C6 1.450(7) . ? O2 C7 1.365(6) . ? O2 C6 1.425(6) . ? O3 C15 1.237(6) . ? C1 C2 1.369(7) . ? C1 H1A 0.9300 . ? C2 C3 1.397(7) . ? C2 H2A 0.9300 . ? C3 C4 1.419(7) . ? C3 C17 1.433(7) . ? C4 C5 1.354(7) . ? C4 H4A 0.9300 . ? C5 C7 1.409(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.374(7) . ? C8 C17 1.445(7) . ? C8 C9 1.464(7) . ? C9 C14 1.400(7) . ? C9 C10 1.411(7) . ? C10 C11 1.382(8) . ? C10 H10A 0.9300 . ? C11 C12 1.385(8) . ? C11 H11A 0.9300 . ? C12 C13 1.382(8) . ? C12 H12A 0.9300 . ? C13 C14 1.407(7) . ? C13 H13A 0.9300 . ? C14 C15 1.462(7) . ? C15 C16 1.495(7) . ? C16 C17 1.396(7) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 S1 92.46(12) . . ? N1 Pt1 Cl2 174.11(12) . . ? S1 Pt1 Cl2 89.76(5) . . ? N1 Pt1 Cl1 88.00(12) . . ? S1 Pt1 Cl1 178.28(5) . . ? Cl2 Pt1 Cl1 89.94(5) . . ? N1 Pt1 O3 65.93(13) . . ? S1 Pt1 O3 76.29(8) . . ? Cl2 Pt1 O3 119.92(8) . . ? Cl1 Pt1 O3 102.41(8) . . ? O4 S1 C19 108.3(2) . . ? O4 S1 C18 108.3(2) . . ? C19 S1 C18 101.2(3) . . ? O4 S1 Pt1 115.77(16) . . ? C19 S1 Pt1 110.11(19) . . ? C18 S1 Pt1 112.0(2) . . ? C16 N1 C1 118.4(4) . . ? C16 N1 Pt1 127.1(3) . . ? C1 N1 Pt1 113.9(3) . . ? C5 O1 C6 105.6(4) . . ? C7 O2 C6 107.1(4) . . ? C15 O3 Pt1 101.0(3) . . ? N1 C1 C2 122.9(5) . . ? N1 C1 H1A 118.5 . . ? C2 C1 H1A 118.5 . . ? C1 C2 C3 120.1(5) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C2 C3 C4 121.5(5) . . ? C2 C3 C17 117.4(4) . . ? C4 C3 C17 121.0(4) . . ? C5 C4 C3 116.8(5) . . ? C5 C4 H4A 121.6 . . ? C3 C4 H4A 121.6 . . ? C4 C5 O1 127.6(5) . . ? C4 C5 C7 122.3(5) . . ? O1 C5 C7 110.1(4) . . ? O2 C6 O1 106.6(4) . . ? O2 C6 H6A 110.4 . . ? O1 C6 H6A 110.4 . . ? O2 C6 H6B 110.4 . . ? O1 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? O2 C7 C8 127.2(5) . . ? O2 C7 C5 108.3(4) . . ? C8 C7 C5 124.5(5) . . ? C7 C8 C17 114.2(4) . . ? C7 C8 C9 125.2(4) . . ? C17 C8 C9 120.5(4) . . ? C14 C9 C10 118.2(5) . . ? C14 C9 C8 119.1(4) . . ? C10 C9 C8 122.7(5) . . ? C11 C10 C9 120.5(5) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C10 C11 C12 121.1(5) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C13 C12 C11 119.6(5) . . ? C13 C12 H12A 120.2 . . ? C11 C12 H12A 120.2 . . ? C12 C13 C14 120.1(5) . . ? C12 C13 H13A 119.9 . . ? C14 C13 H13A 119.9 . . ? C9 C14 C13 120.5(5) . . ? C9 C14 C15 121.8(5) . . ? C13 C14 C15 117.7(5) . . ? O3 C15 C14 121.6(4) . . ? O3 C15 C16 121.1(4) . . ? C14 C15 C16 117.3(4) . . ? N1 C16 C17 122.2(4) . . ? N1 C16 C15 117.5(4) . . ? C17 C16 C15 120.2(4) . . ? C16 C17 C3 118.7(4) . . ? C16 C17 C8 120.3(4) . . ? C3 C17 C8 121.1(4) . . ? S1 C18 H18A 109.5 . . ? S1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? S1 C19 H19A 109.5 . . ? S1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? S1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 N1 Pt1 S1 O4 -0.4(2) . . . . ? Cl2 Pt1 S1 O4 174.11(17) . . . . ? O3 Pt1 S1 O4 -64.93(18) . . . . ? N1 Pt1 S1 C19 122.8(2) . . . . ? Cl2 Pt1 S1 C19 -62.6(2) . . . . ? O3 Pt1 S1 C19 58.3(2) . . . . ? N1 Pt1 S1 C18 -125.4(2) . . . . ? Cl2 Pt1 S1 C18 49.2(2) . . . . ? O3 Pt1 S1 C18 170.2(2) . . . . ? S1 Pt1 N1 C16 -53.0(4) . . . . ? Cl1 Pt1 N1 C16 125.3(4) . . . . ? O3 Pt1 N1 C16 20.8(4) . . . . ? S1 Pt1 N1 C1 117.4(3) . . . . ? Cl1 Pt1 N1 C1 -64.3(3) . . . . ? O3 Pt1 N1 C1 -168.8(4) . . . . ? N1 Pt1 O3 C15 -22.5(3) . . . . ? S1 Pt1 O3 C15 76.6(3) . . . . ? Cl2 Pt1 O3 C15 158.2(3) . . . . ? Cl1 Pt1 O3 C15 -104.6(3) . . . . ? C16 N1 C1 C2 2.6(8) . . . . ? Pt1 N1 C1 C2 -168.7(4) . . . . ? N1 C1 C2 C3 1.5(8) . . . . ? C1 C2 C3 C4 176.9(5) . . . . ? C1 C2 C3 C17 -2.5(7) . . . . ? C2 C3 C4 C5 -179.0(5) . . . . ? C17 C3 C4 C5 0.3(7) . . . . ? C3 C4 C5 O1 178.3(5) . . . . ? C3 C4 C5 C7 0.4(7) . . . . ? C6 O1 C5 C4 173.5(5) . . . . ? C6 O1 C5 C7 -8.3(6) . . . . ? C7 O2 C6 O1 -15.0(5) . . . . ? C5 O1 C6 O2 14.2(5) . . . . ? C6 O2 C7 C8 -170.6(5) . . . . ? C6 O2 C7 C5 10.0(5) . . . . ? C4 C5 C7 O2 177.3(5) . . . . ? O1 C5 C7 O2 -0.9(6) . . . . ? C4 C5 C7 C8 -2.1(8) . . . . ? O1 C5 C7 C8 179.7(4) . . . . ? O2 C7 C8 C17 -176.6(5) . . . . ? C5 C7 C8 C17 2.7(7) . . . . ? O2 C7 C8 C9 0.8(8) . . . . ? C5 C7 C8 C9 -179.9(5) . . . . ? C7 C8 C9 C14 178.7(5) . . . . ? C17 C8 C9 C14 -4.1(7) . . . . ? C7 C8 C9 C10 0.4(8) . . . . ? C17 C8 C9 C10 177.6(5) . . . . ? C14 C9 C10 C11 0.7(8) . . . . ? C8 C9 C10 C11 179.0(5) . . . . ? C9 C10 C11 C12 -0.2(8) . . . . ? C10 C11 C12 C13 0.5(8) . . . . ? C11 C12 C13 C14 -1.1(8) . . . . ? C10 C9 C14 C13 -1.3(7) . . . . ? C8 C9 C14 C13 -179.7(5) . . . . ? C10 C9 C14 C15 177.9(5) . . . . ? C8 C9 C14 C15 -0.6(7) . . . . ? C12 C13 C14 C9 1.5(8) . . . . ? C12 C13 C14 C15 -177.7(5) . . . . ? Pt1 O3 C15 C14 -159.9(4) . . . . ? Pt1 O3 C15 C16 22.8(5) . . . . ? C9 C14 C15 O3 -169.6(5) . . . . ? C13 C14 C15 O3 9.6(7) . . . . ? C9 C14 C15 C16 7.9(7) . . . . ? C13 C14 C15 C16 -172.9(4) . . . . ? C1 N1 C16 C17 -5.6(7) . . . . ? Pt1 N1 C16 C17 164.4(4) . . . . ? C1 N1 C16 C15 172.0(4) . . . . ? Pt1 N1 C16 C15 -18.0(6) . . . . ? O3 C15 C16 N1 -11.3(7) . . . . ? C14 C15 C16 N1 171.3(4) . . . . ? O3 C15 C16 C17 166.4(5) . . . . ? C14 C15 C16 C17 -11.1(7) . . . . ? N1 C16 C17 C3 4.6(7) . . . . ? C15 C16 C17 C3 -173.0(4) . . . . ? N1 C16 C17 C8 -175.6(5) . . . . ? C15 C16 C17 C8 6.9(7) . . . . ? C2 C3 C17 C16 -0.4(7) . . . . ? C4 C3 C17 C16 -179.7(4) . . . . ? C2 C3 C17 C8 179.8(5) . . . . ? C4 C3 C17 C8 0.4(7) . . . . ? C7 C8 C17 C16 178.3(4) . . . . ? C9 C8 C17 C16 0.8(7) . . . . ? C7 C8 C17 C3 -1.9(7) . . . . ? C9 C8 C17 C3 -179.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.082 _refine_diff_density_min -1.325 _refine_diff_density_rms 0.138 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 670190' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H9 N O3, 2(H Cl3)' _chemical_formula_sum 'C19 H11 Cl6 N O3' _chemical_formula_weight 513.99 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' _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 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 26.529(5) _cell_length_b 12.4079(18) _cell_length_c 13.862(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.135(4) _cell_angle_gamma 90.00 _cell_volume 4164.2(12) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6637 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 0.847 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7017 _exptl_absorpt_correction_T_max 0.8488 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20281 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3817 _reflns_number_gt 3162 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0878P)^2^+18.8362P] 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 3817 _refine_ls_number_parameters 276 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0843 _refine_ls_wR_factor_ref 0.2167 _refine_ls_wR_factor_gt 0.2064 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.219 _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 Cl1 Cl 0.27076(9) 0.80592(15) 0.21479(15) 0.0836(6) Uani 1 1 d . . . Cl2 Cl 0.21856(6) 0.75490(15) 0.35597(13) 0.0702(5) Uani 1 1 d . . . Cl3 Cl 0.25879(7) 0.58484(13) 0.26622(14) 0.0670(5) Uani 1 1 d . . . Cl4A Cl 0.4556(3) 1.0427(5) 0.6597(6) 0.0600(16) Uiso 0.25 1 d PD . . Cl4B Cl 0.45085(18) 1.0528(3) 0.6084(5) 0.0775(11) Uiso 0.50 1 d P . . Cl4C Cl 0.4406(3) 1.0472(5) 0.5558(7) 0.0638(17) Uiso 0.25 1 d PD . . Cl5A Cl 0.3741(5) 1.0109(9) 0.4491(7) 0.092(3) Uiso 0.25 1 d PD . . Cl5B Cl 0.3333(3) 0.9742(5) 0.4593(5) 0.1190(19) Uiso 0.50 1 d PD . . Cl5C Cl 0.3533(4) 0.9809(6) 0.4414(5) 0.0614(16) Uiso 0.25 1 d PD . . Cl6A Cl 0.3429(4) 1.0021(7) 0.6184(8) 0.078(2) Uiso 0.25 1 d PD . . Cl6B Cl 0.3613(2) 0.9984(4) 0.6644(5) 0.0690(12) Uiso 0.50 1 d P . . Cl6C Cl 0.3802(4) 1.0040(8) 0.6908(8) 0.079(3) Uiso 0.25 1 d P . . O1 O 0.36966(14) 0.7177(3) 0.5550(3) 0.0461(8) Uani 1 1 d . . . O2 O 0.60965(14) 0.3350(3) 0.6626(3) 0.0510(9) Uani 1 1 d . . . O3 O 0.52009(14) 0.2882(3) 0.6302(3) 0.0478(9) Uani 1 1 d . . . N1 N 0.47654(17) 0.7716(3) 0.6121(3) 0.0425(9) Uani 1 1 d . . . C1 C 0.40330(18) 0.6443(4) 0.5772(3) 0.0350(10) Uani 1 1 d . . . C2 C 0.46325(18) 0.6680(4) 0.6069(3) 0.0352(10) Uani 1 1 d . . . C3 C 0.50102(18) 0.5820(4) 0.6244(3) 0.0318(9) Uani 1 1 d . . . C4 C 0.48320(17) 0.4720(4) 0.6171(3) 0.0310(9) Uani 1 1 d . . . C5 C 0.42549(18) 0.4464(4) 0.5924(3) 0.0343(10) Uani 1 1 d . . . C6 C 0.38706(18) 0.5307(4) 0.5735(3) 0.0329(9) Uani 1 1 d . . . C7 C 0.5294(2) 0.7958(4) 0.6365(4) 0.0483(12) Uani 1 1 d . . . H7 H 0.5396 0.8697 0.6423 0.058 Uiso 1 1 calc R . . C8 C 0.5698(2) 0.7198(4) 0.6536(4) 0.0456(12) Uani 1 1 d . . . H8 H 0.6066 0.7419 0.6695 0.055 Uiso 1 1 calc R . . C9 C 0.55705(18) 0.6106(4) 0.6477(3) 0.0361(10) Uani 1 1 d . . . C10 C 0.59724(18) 0.5289(4) 0.6632(3) 0.0383(11) Uani 1 1 d . . . H10 H 0.6347 0.5456 0.6789 0.046 Uiso 1 1 calc R . . C11 C 0.57910(19) 0.4263(4) 0.6546(3) 0.0386(11) Uani 1 1 d . . . C12 C 0.52470(19) 0.3974(4) 0.6343(3) 0.0357(10) Uani 1 1 d . . . C13 C 0.5742(2) 0.2464(4) 0.6550(4) 0.0498(13) Uani 1 1 d . . . H13A H 0.5876 0.2067 0.7228 0.060 Uiso 1 1 calc R . . H13B H 0.5734 0.1962 0.5989 0.060 Uiso 1 1 calc R . . C14 C 0.3315(2) 0.5071(4) 0.5502(4) 0.0413(11) Uani 1 1 d . . . H14 H 0.3059 0.5644 0.5382 0.050 Uiso 1 1 calc R . . C15 C 0.3138(2) 0.4023(5) 0.5444(4) 0.0488(12) Uani 1 1 d . . . H15 H 0.2761 0.3869 0.5283 0.059 Uiso 1 1 calc R . . C16 C 0.3515(2) 0.3193(5) 0.5624(4) 0.0506(13) Uani 1 1 d . . . H16 H 0.3395 0.2467 0.5587 0.061 Uiso 1 1 calc R . . C17 C 0.4059(2) 0.3404(4) 0.5854(4) 0.0426(11) Uani 1 1 d . . . H17 H 0.4309 0.2820 0.5967 0.051 Uiso 1 1 calc R . . C18 C 0.2694(2) 0.7174(4) 0.3124(4) 0.0447(12) Uani 1 1 d . . . H18 H 0.3061 0.7211 0.3740 0.054 Uiso 1 1 calc R . . C19 C 0.3945(2) 0.9690(5) 0.5798(5) 0.0602(15) Uani 1 1 d D . . H13 H 0.404(2) 0.898(4) 0.586(4) 0.040(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1173(15) 0.0649(10) 0.0789(11) 0.0247(9) 0.0506(11) 0.0242(10) Cl2 0.0458(8) 0.0957(12) 0.0722(10) -0.0203(9) 0.0272(7) 0.0109(8) Cl3 0.0618(9) 0.0556(9) 0.0883(11) -0.0182(8) 0.0355(8) -0.0077(7) O1 0.0368(18) 0.0409(19) 0.059(2) -0.0008(16) 0.0181(16) 0.0095(15) O2 0.0429(19) 0.054(2) 0.059(2) 0.0039(17) 0.0232(17) 0.0175(17) O3 0.047(2) 0.0403(19) 0.058(2) 0.0049(16) 0.0234(17) 0.0116(15) N1 0.040(2) 0.038(2) 0.049(2) -0.0052(18) 0.0167(19) -0.0002(18) C1 0.035(2) 0.042(3) 0.030(2) -0.0028(18) 0.0146(18) 0.002(2) C2 0.036(2) 0.040(3) 0.030(2) -0.0029(18) 0.0147(19) 0.0038(19) C3 0.033(2) 0.041(2) 0.0219(19) -0.0016(17) 0.0115(17) 0.0052(19) C4 0.033(2) 0.040(2) 0.023(2) 0.0024(17) 0.0139(17) 0.0066(18) C5 0.037(2) 0.043(3) 0.023(2) 0.0007(18) 0.0127(18) 0.0048(19) C6 0.035(2) 0.040(2) 0.026(2) 0.0001(18) 0.0156(18) 0.0033(19) C7 0.044(3) 0.042(3) 0.058(3) -0.006(2) 0.020(2) -0.007(2) C8 0.034(2) 0.056(3) 0.045(3) -0.004(2) 0.014(2) -0.004(2) C9 0.030(2) 0.053(3) 0.025(2) -0.0011(19) 0.0117(18) 0.003(2) C10 0.029(2) 0.057(3) 0.029(2) 0.001(2) 0.0107(18) 0.005(2) C11 0.038(2) 0.052(3) 0.031(2) 0.003(2) 0.018(2) 0.016(2) C12 0.042(2) 0.040(3) 0.028(2) 0.0042(18) 0.0162(19) 0.009(2) C13 0.054(3) 0.046(3) 0.052(3) 0.010(2) 0.025(3) 0.021(2) C14 0.038(2) 0.050(3) 0.039(2) -0.001(2) 0.019(2) 0.004(2) C15 0.038(3) 0.057(3) 0.054(3) -0.003(2) 0.022(2) -0.007(2) C16 0.055(3) 0.045(3) 0.056(3) 0.000(2) 0.028(3) -0.007(2) C17 0.043(3) 0.040(3) 0.049(3) 0.005(2) 0.023(2) 0.004(2) C18 0.038(3) 0.051(3) 0.043(3) -0.001(2) 0.014(2) 0.008(2) C19 0.063(4) 0.041(3) 0.076(4) -0.004(3) 0.027(3) 0.010(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 Cl1 C18 1.754(5) . ? Cl2 C18 1.751(5) . ? Cl3 C18 1.745(5) . ? Cl4A C19 1.795(8) . ? Cl4B C19 1.728(7) . ? Cl4C C19 1.696(8) . ? Cl5A C19 1.745(10) . ? Cl5B C19 1.793(8) . ? Cl5C C19 1.784(9) . ? Cl6A C19 1.713(9) . ? Cl6B C19 1.769(8) . ? Cl6C C19 1.783(11) . ? O1 C1 1.223(5) . ? O2 C11 1.371(6) . ? O2 C13 1.422(7) . ? O3 C12 1.359(6) . ? O3 C13 1.429(6) . ? N1 C2 1.327(6) . ? N1 C7 1.336(7) . ? C1 C6 1.469(6) . ? C1 C2 1.500(6) . ? C2 C3 1.415(6) . ? C3 C9 1.431(6) . ? C3 C4 1.434(6) . ? C4 C12 1.382(6) . ? C4 C5 1.461(6) . ? C5 C17 1.403(7) . ? C5 C6 1.408(6) . ? C6 C14 1.404(6) . ? C7 C8 1.373(7) . ? C7 H7 0.9500 . ? C8 C9 1.391(7) . ? C8 H8 0.9500 . ? C9 C10 1.422(6) . ? C10 C11 1.349(7) . ? C10 H10 0.9500 . ? C11 C12 1.400(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.375(7) . ? C14 H14 0.9500 . ? C15 C16 1.385(8) . ? C15 H15 0.9500 . ? C16 C17 1.371(7) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18 1.0000 . ? C19 H13 0.91(5) . ? 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 C11 O2 C13 106.3(4) . . ? C12 O3 C13 106.7(4) . . ? C2 N1 C7 117.4(4) . . ? O1 C1 C6 122.1(4) . . ? O1 C1 C2 120.4(4) . . ? C6 C1 C2 117.4(4) . . ? N1 C2 C3 124.6(4) . . ? N1 C2 C1 115.6(4) . . ? C3 C2 C1 119.8(4) . . ? C2 C3 C9 116.7(4) . . ? C2 C3 C4 121.0(4) . . ? C9 C3 C4 122.3(4) . . ? C12 C4 C3 114.1(4) . . ? C12 C4 C5 125.4(4) . . ? C3 C4 C5 120.5(4) . . ? C17 C5 C6 117.7(4) . . ? C17 C5 C4 122.9(4) . . ? C6 C5 C4 119.5(4) . . ? C14 C6 C5 120.0(4) . . ? C14 C6 C1 118.2(4) . . ? C5 C6 C1 121.8(4) . . ? N1 C7 C8 123.6(5) . . ? N1 C7 H7 118.2 . . ? C8 C7 H7 118.2 . . ? C7 C8 C9 120.3(5) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 122.4(4) . . ? C8 C9 C3 117.4(4) . . ? C10 C9 C3 120.2(4) . . ? C11 C10 C9 116.2(4) . . ? C11 C10 H10 121.9 . . ? C9 C10 H10 121.9 . . ? C10 C11 O2 126.5(4) . . ? C10 C11 C12 124.1(4) . . ? O2 C11 C12 109.4(4) . . ? O3 C12 C4 127.5(4) . . ? O3 C12 C11 109.3(4) . . ? C4 C12 C11 123.1(4) . . ? O2 C13 O3 107.8(4) . . ? O2 C13 H13A 110.1 . . ? O3 C13 H13A 110.1 . . ? O2 C13 H13B 110.1 . . ? O3 C13 H13B 110.1 . . ? H13A C13 H13B 108.5 . . ? C15 C14 C6 120.9(5) . . ? C15 C14 H14 119.6 . . ? C6 C14 H14 119.6 . . ? C14 C15 C16 119.2(5) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C17 C16 C15 121.0(5) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C5 121.3(5) . . ? C16 C17 H17 119.4 . . ? C5 C17 H17 119.4 . . ? Cl3 C18 Cl2 110.2(3) . . ? Cl3 C18 Cl1 111.0(3) . . ? Cl2 C18 Cl1 111.2(3) . . ? Cl3 C18 H18 108.1 . . ? Cl2 C18 H18 108.1 . . ? Cl1 C18 H18 108.1 . . ? Cl4C C19 Cl6A 131.0(5) . . ? Cl4C C19 Cl4B 22.6(2) . . ? Cl6A C19 Cl4B 120.7(5) . . ? Cl4C C19 Cl5A 64.5(5) . . ? Cl6A C19 Cl5A 107.7(6) . . ? Cl4B C19 Cl5A 86.1(5) . . ? Cl4C C19 Cl6B 127.3(5) . . ? Cl6A C19 Cl6B 20.7(3) . . ? Cl4B C19 Cl6B 110.0(4) . . ? Cl5A C19 Cl6B 126.8(5) . . ? Cl4C C19 Cl6C 117.1(5) . . ? Cl6A C19 Cl6C 36.1(5) . . ? Cl4B C19 Cl6C 97.2(5) . . ? Cl5A C19 Cl6C 137.6(6) . . ? Cl6B C19 Cl6C 15.8(3) . . ? Cl4C C19 Cl5C 85.2(5) . . ? Cl6A C19 Cl5C 95.7(5) . . ? Cl4B C19 Cl5C 106.8(5) . . ? Cl5A C19 Cl5C 20.8(3) . . ? Cl6B C19 Cl5C 116.3(5) . . ? Cl6C C19 Cl5C 130.9(5) . . ? Cl4C C19 Cl5B 104.3(5) . . ? Cl6A C19 Cl5B 75.3(5) . . ? Cl4B C19 Cl5B 124.2(5) . . ? Cl5A C19 Cl5B 40.8(4) . . ? Cl6B C19 Cl5B 95.9(4) . . ? Cl6C C19 Cl5B 111.3(5) . . ? Cl5C C19 Cl5B 21.8(3) . . ? Cl4C C19 Cl4A 44.7(4) . . ? Cl6A C19 Cl4A 108.7(5) . . ? Cl4B C19 Cl4A 22.2(2) . . ? Cl5A C19 Cl4A 108.0(6) . . ? Cl6B C19 Cl4A 93.1(4) . . ? Cl6C C19 Cl4A 78.5(5) . . ? Cl5C C19 Cl4A 128.6(5) . . ? Cl5B C19 Cl4A 143.4(5) . . ? Cl4C C19 H13 113(3) . . ? Cl6A C19 H13 115(3) . . ? Cl4B C19 H13 113(3) . . ? Cl5A C19 H13 110(3) . . ? Cl6B C19 H13 109(3) . . ? Cl6C C19 H13 107(3) . . ? Cl5C C19 H13 102(3) . . ? Cl5B C19 H13 103(3) . . ? Cl4A C19 H13 107(3) . . ? 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 C7 N1 C2 C3 -0.6(7) . . . . ? C7 N1 C2 C1 -178.8(4) . . . . ? O1 C1 C2 N1 3.2(6) . . . . ? C6 C1 C2 N1 -178.3(4) . . . . ? O1 C1 C2 C3 -175.2(4) . . . . ? C6 C1 C2 C3 3.4(6) . . . . ? N1 C2 C3 C9 -1.0(6) . . . . ? C1 C2 C3 C9 177.2(4) . . . . ? N1 C2 C3 C4 -180.0(4) . . . . ? C1 C2 C3 C4 -1.8(6) . . . . ? C2 C3 C4 C12 178.9(4) . . . . ? C9 C3 C4 C12 -0.1(5) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C9 C3 C4 C5 -179.6(4) . . . . ? C12 C4 C5 C17 1.2(6) . . . . ? C3 C4 C5 C17 -179.4(4) . . . . ? C12 C4 C5 C6 -178.0(4) . . . . ? C3 C4 C5 C6 1.4(6) . . . . ? C17 C5 C6 C14 1.0(6) . . . . ? C4 C5 C6 C14 -179.7(4) . . . . ? C17 C5 C6 C1 -178.9(4) . . . . ? C4 C5 C6 C1 0.4(6) . . . . ? O1 C1 C6 C14 -4.1(6) . . . . ? C2 C1 C6 C14 177.4(4) . . . . ? O1 C1 C6 C5 175.8(4) . . . . ? C2 C1 C6 C5 -2.7(6) . . . . ? C2 N1 C7 C8 1.6(8) . . . . ? N1 C7 C8 C9 -1.0(8) . . . . ? C7 C8 C9 C10 179.1(4) . . . . ? C7 C8 C9 C3 -0.6(7) . . . . ? C2 C3 C9 C8 1.5(6) . . . . ? C4 C3 C9 C8 -179.5(4) . . . . ? C2 C3 C9 C10 -178.2(4) . . . . ? C4 C3 C9 C10 0.8(6) . . . . ? C8 C9 C10 C11 -179.6(4) . . . . ? C3 C9 C10 C11 0.1(6) . . . . ? C9 C10 C11 O2 177.6(4) . . . . ? C9 C10 C11 C12 -1.7(6) . . . . ? C13 O2 C11 C10 176.3(5) . . . . ? C13 O2 C11 C12 -4.3(5) . . . . ? C13 O3 C12 C4 -179.3(4) . . . . ? C13 O3 C12 C11 3.6(5) . . . . ? C3 C4 C12 O3 -178.3(4) . . . . ? C5 C4 C12 O3 1.2(7) . . . . ? C3 C4 C12 C11 -1.5(6) . . . . ? C5 C4 C12 C11 178.0(4) . . . . ? C10 C11 C12 O3 179.9(4) . . . . ? O2 C11 C12 O3 0.5(5) . . . . ? C10 C11 C12 C4 2.6(7) . . . . ? O2 C11 C12 C4 -176.8(4) . . . . ? C11 O2 C13 O3 6.5(5) . . . . ? C12 O3 C13 O2 -6.2(5) . . . . ? C5 C6 C14 C15 -0.7(7) . . . . ? C1 C6 C14 C15 179.2(4) . . . . ? C6 C14 C15 C16 0.3(7) . . . . ? C14 C15 C16 C17 -0.2(8) . . . . ? C15 C16 C17 C5 0.6(8) . . . . ? C6 C5 C17 C16 -1.0(7) . . . . ? C4 C5 C17 C16 179.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.864 _refine_diff_density_min -1.041 _refine_diff_density_rms 0.082