# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Muhammad Hanif' ; Institut fuer Anorganische Chemie, Universitaet Wien Waehringerstr. 42 A-1090 Vienna Austria ; 'Alexey A. Nazarov' ; Institut fuer Anorganische Chemie Universitaet Wien Waehringerstr. 42 A-1090 Vienna Austria ; 'Anton Legin' ; Institut fuer Anorganische Chemie Universitaet Wien Waehringerstr. 42 A-1090 Vienna Austria ; 'Michael Groessl' ; Institut des Sciences et Ingenierie Chimiques, Ecole Polytechnique Federale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland ; 'Vladimir B. Arion' ; Institut fuer Anorganische Chemie Universitaet Wien Waehringerstr. 42 A-1090 Vienna Austria ; 'Michael A. Jakupec' ; Institut fuer Anorganische Chemie Universitaet Wien Waehringerstr. 42 A-1090 Vienna Austria ; 'Yuri O. Tsybin' ; Institut des Sciences et Ingenierie Chimiques, Ecole Polytechnique Federale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland ; 'Paul Dyson' ; Institut des Sciences et Ingenierie Chimiques, Ecole Polytechnique Federale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland ; 'Bernhard K. Keppler' ; Institut fuer Anorganische Chemie Universitaet Wien Waehringerstr. 42 A-1090 Vienna Austria ; 'Christian G. Hartinger' ; Institut fuer Anorganische Chemie Universitaet Wien Waehringerstr. 42 A-1090 Vienna Austria ; _publ_section_title ; Maleimide-functionalized organometallic ruthenium anticancer agents for the delivery of cytotoxic moieties to the tumour tissue ; _publ_contact_author_name 'Vladimir Arion' _publ_contact_author_email vladimir.arion@univie.ac.at data_MUHA081 _database_code_depnum_ccdc_archive 'CCDC 837010' #TrackingRef 'MUHA081.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dichlorido(hapto^6^-N-benzylmaleimide)(1,3,5-triaza-7-phospha- tricyclo[3.3.1.1]decane)ruthenium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 Cl2 N4 O2 P Ru, C H4 O' _chemical_formula_sum 'C18 H25 Cl2 N4 O3 P Ru' _chemical_formula_weight 548.36 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' P P 0.1023 0.0942 '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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 14.2423(7) _cell_length_b 11.6629(6) _cell_length_c 13.1191(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.589(2) _cell_angle_gamma 90.00 _cell_volume 2148.72(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9874 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 29.40 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.98 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 1.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4183 _exptl_absorpt_correction_T_max 0.9301 _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 'Bruker APEX-II CCD' _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 107474 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5194 _reflns_number_gt 4440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0483P)^2^+2.4453P] 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 5194 _refine_ls_number_parameters 271 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 Ru1 Ru 0.318209(14) 0.147954(16) 0.049694(14) 0.02030(7) Uani 1 1 d . . . Cl1 Cl 0.19435(4) 0.18784(6) -0.09448(4) 0.02768(14) Uani 1 1 d . . . Cl2 Cl 0.43268(4) 0.21916(5) -0.05257(4) 0.02749(14) Uani 1 1 d . . . P1 P 0.29633(5) 0.33842(5) 0.08503(5) 0.02173(14) Uani 1 1 d . . . O1 O 0.05605(16) -0.19193(18) 0.01211(15) 0.0379(5) Uani 1 1 d . . . O2 O 0.09699(15) 0.0083(2) 0.31385(16) 0.0418(5) Uani 1 1 d . . . N1 N 0.35245(19) 0.53072(19) 0.20059(18) 0.0345(5) Uani 1 1 d . . . N2 N 0.17910(18) 0.50096(19) 0.14854(18) 0.0326(5) Uani 1 1 d . . . N3 N 0.27681(18) 0.56190(19) 0.01896(18) 0.0330(5) Uani 1 1 d D . . N4 N 0.08280(16) -0.06741(19) 0.15052(17) 0.0275(5) Uani 1 1 d . . . C1 C 0.3800(2) 0.4107(2) 0.1875(2) 0.0302(6) Uani 1 1 d . . . H1A H 0.3814 0.3692 0.2536 0.036 Uiso 1 1 calc R . . H1B H 0.4448 0.4084 0.1698 0.036 Uiso 1 1 calc R . . C2 C 0.18386(19) 0.3770(2) 0.1278(2) 0.0272(5) Uani 1 1 d . . . H2A H 0.1298 0.3551 0.0737 0.033 Uiso 1 1 calc R . . H2B H 0.1781 0.3338 0.1914 0.033 Uiso 1 1 calc R . . C3 C 0.2947(2) 0.4456(2) -0.01857(19) 0.0271(5) Uani 1 1 d . . . H3A H 0.3566 0.4446 -0.0435 0.033 Uiso 1 1 calc R . . H3B H 0.2443 0.4256 -0.0774 0.033 Uiso 1 1 calc R . . C4 C 0.2569(2) 0.5373(2) 0.2304(2) 0.0356(6) Uani 1 1 d . . . H4A H 0.2562 0.4885 0.2920 0.043 Uiso 1 1 calc R . . H4B H 0.2451 0.6173 0.2500 0.043 Uiso 1 1 calc R . . C5 C 0.3517(2) 0.5967(2) 0.1051(2) 0.0375(6) Uani 1 1 d . . . H5A H 0.4144 0.5885 0.0830 0.045 Uiso 1 1 calc R . . H5B H 0.3429 0.6789 0.1202 0.045 Uiso 1 1 calc R . . C6 C 0.1834(2) 0.5673(2) 0.0552(2) 0.0383(7) Uani 1 1 d . . . H6A H 0.1689 0.6484 0.0684 0.046 Uiso 1 1 calc R . . H6B H 0.1334 0.5390 -0.0008 0.046 Uiso 1 1 calc R . . C7 C 0.2803(2) 0.0956(2) 0.19685(18) 0.0266(5) Uani 1 1 d . . . H7 H 0.2486 0.1374 0.2431 0.032 Uiso 1 1 calc R . . C8 C 0.22674(18) 0.0297(2) 0.11656(19) 0.0252(5) Uani 1 1 d . . . C9 C 0.2758(2) -0.0388(2) 0.0515(2) 0.0270(5) Uani 1 1 d . . . H9 H 0.2406 -0.0873 0.0008 0.032 Uiso 1 1 calc R . . C10 C 0.37438(19) -0.0348(2) 0.0620(2) 0.0290(6) Uani 1 1 d . . . H10 H 0.4064 -0.0804 0.0185 0.035 Uiso 1 1 calc R . . C11 C 0.42743(19) 0.0375(2) 0.1379(2) 0.0293(6) Uani 1 1 d . . . H11 H 0.4943 0.0445 0.1414 0.035 Uiso 1 1 calc R . . C12 C 0.3814(2) 0.0991(2) 0.20816(19) 0.0301(6) Uani 1 1 d . . . H12 H 0.4175 0.1424 0.2623 0.036 Uiso 1 1 calc R . . C13 C 0.05632(19) -0.1724(2) 0.1030(2) 0.0273(5) Uani 1 1 d . . . C14 C 0.0330(2) -0.2514(2) 0.1854(2) 0.0305(6) Uani 1 1 d . . . H14 H 0.0145 -0.3295 0.1766 0.037 Uiso 1 1 calc R . . C15 C 0.0432(2) -0.1895(3) 0.2770(2) 0.0354(6) Uani 1 1 d . . . H15 H 0.0308 -0.2167 0.3417 0.043 Uiso 1 1 calc R . . C16 C 0.07736(18) -0.0722(2) 0.2552(2) 0.0300(6) Uani 1 1 d . . . C17 C 0.11849(19) 0.0302(2) 0.0995(2) 0.0306(6) Uani 1 1 d . . . H17A H 0.0958 0.1021 0.1272 0.037 Uiso 1 1 calc R . . H17B H 0.0935 0.0271 0.0245 0.037 Uiso 1 1 calc R . . C18 C 0.3675(10) 0.703(2) -0.164(3) 0.036(2) Uani 0.50 1 d PD A 1 H18A H 0.3940 0.7759 -0.1841 0.055 Uiso 0.50 1 calc PR A 1 H18B H 0.3608 0.6497 -0.2222 0.055 Uiso 0.50 1 calc PR A 1 H18C H 0.4102 0.6706 -0.1049 0.055 Uiso 0.50 1 calc PR A 1 O3 O 0.2771(7) 0.7236(7) -0.1362(6) 0.0504(16) Uani 0.50 1 d PD A 1 H3 H 0.2641 0.6700 -0.0982 0.076 Uiso 0.50 1 d PR A 1 C18X C 0.3718(10) 0.686(2) -0.171(3) 0.036(2) Uani 0.50 1 d PD B 2 H18D H 0.3867 0.7201 -0.2352 0.055 Uiso 0.50 1 calc PR B 2 H18E H 0.3953 0.6068 -0.1653 0.055 Uiso 0.50 1 calc PR B 2 H18F H 0.4026 0.7305 -0.1119 0.055 Uiso 0.50 1 calc PR B 2 O3X O 0.2722(7) 0.6865(7) -0.1744(6) 0.0504(16) Uani 0.50 1 d PD B 2 H3X H 0.2596 0.6612 -0.1183 0.076 Uiso 0.50 1 d PRD B 2 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 0.02428(12) 0.02127(11) 0.01499(10) 0.00191(6) 0.00219(7) 0.00472(7) Cl1 0.0300(3) 0.0324(3) 0.0188(3) 0.0025(2) -0.0015(2) 0.0045(3) Cl2 0.0288(3) 0.0320(3) 0.0232(3) 0.0049(2) 0.0087(2) 0.0065(2) P1 0.0270(3) 0.0215(3) 0.0164(3) 0.0024(2) 0.0029(2) 0.0042(2) O1 0.0524(13) 0.0359(11) 0.0248(10) -0.0025(8) 0.0045(9) 0.0097(10) O2 0.0353(11) 0.0517(13) 0.0375(11) -0.0153(10) 0.0030(9) -0.0011(10) N1 0.0483(15) 0.0236(11) 0.0301(12) 0.0002(9) 0.0021(10) -0.0003(10) N2 0.0423(14) 0.0267(11) 0.0306(11) -0.0025(9) 0.0116(10) 0.0092(10) N3 0.0484(15) 0.0223(11) 0.0306(12) 0.0057(9) 0.0132(10) 0.0065(10) N4 0.0285(11) 0.0283(11) 0.0261(11) 0.0026(8) 0.0054(9) 0.0020(9) C1 0.0356(15) 0.0257(13) 0.0265(13) -0.0006(10) -0.0028(11) -0.0004(11) C2 0.0321(14) 0.0271(12) 0.0237(12) -0.0010(10) 0.0081(10) 0.0036(10) C3 0.0338(14) 0.0259(12) 0.0223(11) 0.0036(9) 0.0063(10) 0.0057(10) C4 0.0537(18) 0.0261(13) 0.0285(13) -0.0047(10) 0.0111(12) 0.0004(12) C5 0.0465(18) 0.0261(14) 0.0402(16) 0.0012(12) 0.0080(13) -0.0005(12) C6 0.0505(18) 0.0302(14) 0.0352(15) 0.0048(11) 0.0099(13) 0.0166(13) C7 0.0397(15) 0.0224(12) 0.0186(11) 0.0050(9) 0.0074(10) 0.0044(11) C8 0.0289(13) 0.0220(12) 0.0249(12) 0.0063(9) 0.0047(10) 0.0035(10) C9 0.0346(14) 0.0210(12) 0.0256(12) 0.0027(9) 0.0055(10) 0.0052(10) C10 0.0354(14) 0.0218(12) 0.0321(13) 0.0067(10) 0.0124(11) 0.0117(10) C11 0.0252(13) 0.0309(13) 0.0305(13) 0.0133(11) 0.0005(10) 0.0066(10) C12 0.0394(15) 0.0285(13) 0.0189(11) 0.0067(10) -0.0052(10) -0.0012(11) C13 0.0257(13) 0.0301(13) 0.0258(12) 0.0017(10) 0.0031(10) 0.0071(10) C14 0.0300(14) 0.0292(13) 0.0318(13) 0.0048(10) 0.0041(11) 0.0001(11) C15 0.0276(14) 0.0521(18) 0.0272(13) 0.0044(12) 0.0065(11) -0.0074(13) C16 0.0207(12) 0.0431(15) 0.0260(13) -0.0032(11) 0.0032(10) 0.0011(11) C17 0.0272(13) 0.0269(13) 0.0377(14) 0.0094(11) 0.0050(11) 0.0056(10) C18 0.040(2) 0.033(6) 0.037(4) 0.001(5) 0.0064(16) 0.000(2) O3 0.0460(18) 0.055(5) 0.053(5) 0.033(3) 0.014(3) 0.009(3) C18X 0.040(2) 0.033(6) 0.037(4) 0.001(5) 0.0064(16) 0.000(2) O3X 0.0460(18) 0.055(5) 0.053(5) 0.033(3) 0.014(3) 0.009(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 Ru1 C7 2.177(2) . ? Ru1 C8 2.179(2) . ? Ru1 C11 2.195(2) . ? Ru1 C12 2.198(2) . ? Ru1 C9 2.262(3) . ? Ru1 C10 2.273(2) . ? Ru1 P1 2.3010(6) . ? Ru1 Cl1 2.4071(6) . ? Ru1 Cl2 2.4242(6) . ? P1 C2 1.839(3) . ? P1 C3 1.844(2) . ? P1 C1 1.845(3) . ? O1 C13 1.213(3) . ? O2 C16 1.217(3) . ? N1 C5 1.469(4) . ? N1 C1 1.471(3) . ? N1 C4 1.478(4) . ? N2 C6 1.458(4) . ? N2 C4 1.471(4) . ? N2 C2 1.475(3) . ? N3 C5 1.476(4) . ? N3 C3 1.479(3) . ? N3 C6 1.486(4) . ? N4 C16 1.390(3) . ? N4 C13 1.397(3) . ? N4 C17 1.454(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.419(4) . ? C7 C12 1.424(4) . ? C7 H7 0.9500 . ? C8 C9 1.433(4) . ? C8 C17 1.520(4) . ? C9 C10 1.389(4) . ? C9 H9 0.9500 . ? C10 C11 1.422(4) . ? C10 H10 0.9500 . ? C11 C12 1.414(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.500(4) . ? C14 C15 1.388(4) . ? C14 H14 0.9500 . ? C15 C16 1.495(4) . ? C15 H15 0.9500 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O3 1.415(8) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O3 H3 0.8400 . ? O3 H3X 0.8166 . ? C18X O3X 1.414(8) . ? C18X H18D 0.9800 . ? C18X H18E 0.9800 . ? C18X H18F 0.9800 . ? O3X H3 1.0441 . ? O3X H3X 0.8400 . ? 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 C7 Ru1 C8 38.02(10) . . ? C7 Ru1 C11 68.09(10) . . ? C8 Ru1 C11 80.51(10) . . ? C7 Ru1 C12 37.97(10) . . ? C8 Ru1 C12 68.49(10) . . ? C11 Ru1 C12 37.54(10) . . ? C7 Ru1 C9 67.32(9) . . ? C8 Ru1 C9 37.59(9) . . ? C11 Ru1 C9 66.21(10) . . ? C12 Ru1 C9 78.98(10) . . ? C7 Ru1 C10 79.08(9) . . ? C8 Ru1 C10 66.73(9) . . ? C11 Ru1 C10 37.07(10) . . ? C12 Ru1 C10 66.82(10) . . ? C9 Ru1 C10 35.68(10) . . ? C7 Ru1 P1 91.73(7) . . ? C8 Ru1 P1 114.82(7) . . ? C11 Ru1 P1 124.63(8) . . ? C12 Ru1 P1 96.16(7) . . ? C9 Ru1 P1 151.92(7) . . ? C10 Ru1 P1 161.60(7) . . ? C7 Ru1 Cl1 119.56(7) . . ? C8 Ru1 Cl1 91.70(7) . . ? C11 Ru1 Cl1 152.85(8) . . ? C12 Ru1 Cl1 157.53(8) . . ? C9 Ru1 Cl1 91.83(7) . . ? C10 Ru1 Cl1 116.11(7) . . ? P1 Ru1 Cl1 82.28(2) . . ? C7 Ru1 Cl2 151.17(7) . . ? C8 Ru1 Cl2 160.36(7) . . ? C11 Ru1 Cl2 90.56(7) . . ? C12 Ru1 Cl2 113.89(8) . . ? C9 Ru1 Cl2 122.77(7) . . ? C10 Ru1 Cl2 95.70(7) . . ? P1 Ru1 Cl2 84.66(2) . . ? Cl1 Ru1 Cl2 88.36(2) . . ? C2 P1 C3 98.88(12) . . ? C2 P1 C1 98.91(13) . . ? C3 P1 C1 98.89(12) . . ? C2 P1 Ru1 116.86(9) . . ? C3 P1 Ru1 119.44(8) . . ? C1 P1 Ru1 119.70(9) . . ? C5 N1 C1 111.3(2) . . ? C5 N1 C4 108.8(2) . . ? C1 N1 C4 110.8(2) . . ? C6 N2 C4 109.1(2) . . ? C6 N2 C2 110.8(2) . . ? C4 N2 C2 111.4(2) . . ? C5 N3 C3 111.4(2) . . ? C5 N3 C6 108.3(2) . . ? C3 N3 C6 111.0(2) . . ? C16 N4 C13 110.5(2) . . ? C16 N4 C17 124.6(2) . . ? C13 N4 C17 124.7(2) . . ? N1 C1 P1 111.57(18) . . ? N1 C1 H1A 109.3 . . ? P1 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? P1 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? N2 C2 P1 111.43(19) . . ? N2 C2 H2A 109.3 . . ? P1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? P1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? N3 C3 P1 110.98(17) . . ? N3 C3 H3A 109.4 . . ? P1 C3 H3A 109.4 . . ? N3 C3 H3B 109.4 . . ? P1 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N2 C4 N1 114.0(2) . . ? N2 C4 H4A 108.8 . . ? N1 C4 H4A 108.8 . . ? N2 C4 H4B 108.8 . . ? N1 C4 H4B 108.8 . . ? H4A C4 H4B 107.6 . . ? N1 C5 N3 114.2(2) . . ? N1 C5 H5A 108.7 . . ? N3 C5 H5A 108.7 . . ? N1 C5 H5B 108.7 . . ? N3 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N2 C6 N3 114.3(2) . . ? N2 C6 H6A 108.7 . . ? N3 C6 H6A 108.7 . . ? N2 C6 H6B 108.7 . . ? N3 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C12 120.1(2) . . ? C8 C7 Ru1 71.08(14) . . ? C12 C7 Ru1 71.82(14) . . ? C8 C7 H7 119.9 . . ? C12 C7 H7 119.9 . . ? Ru1 C7 H7 129.6 . . ? C7 C8 C9 119.3(2) . . ? C7 C8 C17 120.9(2) . . ? C9 C8 C17 119.8(2) . . ? C7 C8 Ru1 70.90(14) . . ? C9 C8 Ru1 74.32(15) . . ? C17 C8 Ru1 126.72(17) . . ? C10 C9 C8 120.5(2) . . ? C10 C9 Ru1 72.60(15) . . ? C8 C9 Ru1 68.08(14) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? Ru1 C9 H9 132.6 . . ? C9 C10 C11 120.0(2) . . ? C9 C10 Ru1 71.72(14) . . ? C11 C10 Ru1 68.48(14) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? Ru1 C10 H10 132.9 . . ? C12 C11 C10 120.5(2) . . ? C12 C11 Ru1 71.36(14) . . ? C10 C11 Ru1 74.45(14) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? Ru1 C11 H11 126.3 . . ? C11 C12 C7 119.2(2) . . ? C11 C12 Ru1 71.10(14) . . ? C7 C12 Ru1 70.21(13) . . ? C11 C12 H12 120.4 . . ? C7 C12 H12 120.4 . . ? Ru1 C12 H12 130.9 . . ? O1 C13 N4 124.1(3) . . ? O1 C13 C14 128.9(3) . . ? N4 C13 C14 107.0(2) . . ? C15 C14 C13 107.5(2) . . ? C15 C14 H14 126.3 . . ? C13 C14 H14 126.3 . . ? C14 C15 C16 107.6(2) . . ? C14 C15 H15 126.2 . . ? C16 C15 H15 126.2 . . ? O2 C16 N4 123.3(3) . . ? O2 C16 C15 129.3(3) . . ? N4 C16 C15 107.4(2) . . ? N4 C17 C8 110.7(2) . . ? N4 C17 H17A 109.5 . . ? C8 C17 H17A 109.5 . . ? N4 C17 H17B 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C18 O3 H3 109.2 . . ? C18 O3 H3X 105.0 . . ? O3X C18X H18D 109.5 . . ? O3X C18X H18E 109.5 . . ? H18D C18X H18E 109.5 . . ? O3X C18X H18F 109.5 . . ? H18D C18X H18F 109.5 . . ? H18E C18X H18F 109.5 . . ? C18X O3X H3 104.0 . . ? C18X O3X H3X 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 C7 Ru1 P1 C2 -50.01(12) . . . . ? C8 Ru1 P1 C2 -18.70(12) . . . . ? C11 Ru1 P1 C2 -114.36(13) . . . . ? C12 Ru1 P1 C2 -87.83(12) . . . . ? C9 Ru1 P1 C2 -9.72(18) . . . . ? C10 Ru1 P1 C2 -109.4(2) . . . . ? Cl1 Ru1 P1 C2 69.59(10) . . . . ? Cl2 Ru1 P1 C2 158.65(10) . . . . ? C7 Ru1 P1 C3 -168.99(13) . . . . ? C8 Ru1 P1 C3 -137.68(13) . . . . ? C11 Ru1 P1 C3 126.66(13) . . . . ? C12 Ru1 P1 C3 153.19(13) . . . . ? C9 Ru1 P1 C3 -128.70(17) . . . . ? C10 Ru1 P1 C3 131.7(2) . . . . ? Cl1 Ru1 P1 C3 -49.39(11) . . . . ? Cl2 Ru1 P1 C3 39.67(11) . . . . ? C7 Ru1 P1 C1 69.25(13) . . . . ? C8 Ru1 P1 C1 100.56(13) . . . . ? C11 Ru1 P1 C1 4.90(14) . . . . ? C12 Ru1 P1 C1 31.44(13) . . . . ? C9 Ru1 P1 C1 109.55(18) . . . . ? C10 Ru1 P1 C1 9.9(2) . . . . ? Cl1 Ru1 P1 C1 -171.14(11) . . . . ? Cl2 Ru1 P1 C1 -82.08(11) . . . . ? C5 N1 C1 P1 -60.4(3) . . . . ? C4 N1 C1 P1 60.8(3) . . . . ? C2 P1 C1 N1 -50.2(2) . . . . ? C3 P1 C1 N1 50.3(2) . . . . ? Ru1 P1 C1 N1 -178.25(15) . . . . ? C6 N2 C2 P1 61.4(3) . . . . ? C4 N2 C2 P1 -60.4(2) . . . . ? C3 P1 C2 N2 -50.9(2) . . . . ? C1 P1 C2 N2 49.7(2) . . . . ? Ru1 P1 C2 N2 179.59(14) . . . . ? C5 N3 C3 P1 60.6(3) . . . . ? C6 N3 C3 P1 -60.2(3) . . . . ? C2 P1 C3 N3 50.4(2) . . . . ? C1 P1 C3 N3 -50.2(2) . . . . ? Ru1 P1 C3 N3 178.21(15) . . . . ? C6 N2 C4 N1 -54.8(3) . . . . ? C2 N2 C4 N1 67.9(3) . . . . ? C5 N1 C4 N2 54.7(3) . . . . ? C1 N1 C4 N2 -68.0(3) . . . . ? C1 N1 C5 N3 67.3(3) . . . . ? C4 N1 C5 N3 -55.1(3) . . . . ? C3 N3 C5 N1 -67.6(3) . . . . ? C6 N3 C5 N1 54.8(3) . . . . ? C4 N2 C6 N3 54.9(3) . . . . ? C2 N2 C6 N3 -68.1(3) . . . . ? C5 N3 C6 N2 -54.7(3) . . . . ? C3 N3 C6 N2 67.9(3) . . . . ? C11 Ru1 C7 C8 -103.06(16) . . . . ? C12 Ru1 C7 C8 -132.2(2) . . . . ? C9 Ru1 C7 C8 -30.71(14) . . . . ? C10 Ru1 C7 C8 -66.02(15) . . . . ? P1 Ru1 C7 C8 130.03(14) . . . . ? Cl1 Ru1 C7 C8 47.93(16) . . . . ? Cl2 Ru1 C7 C8 -147.92(13) . . . . ? C8 Ru1 C7 C12 132.2(2) . . . . ? C11 Ru1 C7 C12 29.11(15) . . . . ? C9 Ru1 C7 C12 101.46(17) . . . . ? C10 Ru1 C7 C12 66.15(16) . . . . ? P1 Ru1 C7 C12 -97.81(14) . . . . ? Cl1 Ru1 C7 C12 -179.91(13) . . . . ? Cl2 Ru1 C7 C12 -15.8(2) . . . . ? C12 C7 C8 C9 4.0(3) . . . . ? Ru1 C7 C8 C9 58.5(2) . . . . ? C12 C7 C8 C17 -176.5(2) . . . . ? Ru1 C7 C8 C17 -122.0(2) . . . . ? C12 C7 C8 Ru1 -54.5(2) . . . . ? C11 Ru1 C8 C7 66.39(16) . . . . ? C12 Ru1 C8 C7 29.35(15) . . . . ? C9 Ru1 C8 C7 129.4(2) . . . . ? C10 Ru1 C8 C7 102.42(17) . . . . ? P1 Ru1 C8 C7 -57.49(15) . . . . ? Cl1 Ru1 C8 C7 -139.76(14) . . . . ? Cl2 Ru1 C8 C7 130.37(19) . . . . ? C7 Ru1 C8 C9 -129.4(2) . . . . ? C11 Ru1 C8 C9 -63.04(16) . . . . ? C12 Ru1 C8 C9 -100.08(16) . . . . ? C10 Ru1 C8 C9 -27.01(15) . . . . ? P1 Ru1 C8 C9 173.08(12) . . . . ? Cl1 Ru1 C8 C9 90.80(14) . . . . ? Cl2 Ru1 C8 C9 0.9(3) . . . . ? C7 Ru1 C8 C17 114.8(3) . . . . ? C11 Ru1 C8 C17 -178.8(2) . . . . ? C12 Ru1 C8 C17 144.2(2) . . . . ? C9 Ru1 C8 C17 -115.7(3) . . . . ? C10 Ru1 C8 C17 -142.8(3) . . . . ? P1 Ru1 C8 C17 57.3(2) . . . . ? Cl1 Ru1 C8 C17 -24.9(2) . . . . ? Cl2 Ru1 C8 C17 -114.8(2) . . . . ? C7 C8 C9 C10 -4.4(4) . . . . ? C17 C8 C9 C10 176.1(2) . . . . ? Ru1 C8 C9 C10 52.4(2) . . . . ? C7 C8 C9 Ru1 -56.8(2) . . . . ? C17 C8 C9 Ru1 123.7(2) . . . . ? C7 Ru1 C9 C10 -103.29(17) . . . . ? C8 Ru1 C9 C10 -134.3(2) . . . . ? C11 Ru1 C9 C10 -28.23(16) . . . . ? C12 Ru1 C9 C10 -65.39(16) . . . . ? P1 Ru1 C9 C10 -147.76(14) . . . . ? Cl1 Ru1 C9 C10 135.27(15) . . . . ? Cl2 Ru1 C9 C10 46.05(17) . . . . ? C7 Ru1 C9 C8 31.04(15) . . . . ? C11 Ru1 C9 C8 106.10(17) . . . . ? C12 Ru1 C9 C8 68.94(16) . . . . ? C10 Ru1 C9 C8 134.3(2) . . . . ? P1 Ru1 C9 C8 -13.4(2) . . . . ? Cl1 Ru1 C9 C8 -90.40(14) . . . . ? Cl2 Ru1 C9 C8 -179.62(12) . . . . ? C8 C9 C10 C11 0.1(4) . . . . ? Ru1 C9 C10 C11 50.5(2) . . . . ? C8 C9 C10 Ru1 -50.3(2) . . . . ? C7 Ru1 C10 C9 66.14(16) . . . . ? C8 Ru1 C10 C9 28.36(15) . . . . ? C11 Ru1 C10 C9 134.1(2) . . . . ? C12 Ru1 C10 C9 103.89(17) . . . . ? P1 Ru1 C10 C9 127.3(2) . . . . ? Cl1 Ru1 C10 C9 -51.56(16) . . . . ? Cl2 Ru1 C10 C9 -142.53(14) . . . . ? C7 Ru1 C10 C11 -67.97(16) . . . . ? C8 Ru1 C10 C11 -105.75(17) . . . . ? C12 Ru1 C10 C11 -30.23(16) . . . . ? C9 Ru1 C10 C11 -134.1(2) . . . . ? P1 Ru1 C10 C11 -6.8(3) . . . . ? Cl1 Ru1 C10 C11 174.32(13) . . . . ? Cl2 Ru1 C10 C11 83.36(15) . . . . ? C9 C10 C11 C12 4.8(4) . . . . ? Ru1 C10 C11 C12 56.7(2) . . . . ? C9 C10 C11 Ru1 -51.9(2) . . . . ? C7 Ru1 C11 C12 -29.42(16) . . . . ? C8 Ru1 C11 C12 -66.89(16) . . . . ? C9 Ru1 C11 C12 -103.35(17) . . . . ? C10 Ru1 C11 C12 -130.6(2) . . . . ? P1 Ru1 C11 C12 46.80(18) . . . . ? Cl1 Ru1 C11 C12 -141.81(15) . . . . ? Cl2 Ru1 C11 C12 130.69(15) . . . . ? C7 Ru1 C11 C10 101.16(17) . . . . ? C8 Ru1 C11 C10 63.69(16) . . . . ? C12 Ru1 C11 C10 130.6(2) . . . . ? C9 Ru1 C11 C10 27.23(15) . . . . ? P1 Ru1 C11 C10 177.38(12) . . . . ? Cl1 Ru1 C11 C10 -11.2(3) . . . . ? Cl2 Ru1 C11 C10 -98.72(15) . . . . ? C10 C11 C12 C7 -5.2(4) . . . . ? Ru1 C11 C12 C7 53.0(2) . . . . ? C10 C11 C12 Ru1 -58.2(2) . . . . ? C8 C7 C12 C11 0.8(4) . . . . ? Ru1 C7 C12 C11 -53.4(2) . . . . ? C8 C7 C12 Ru1 54.2(2) . . . . ? C7 Ru1 C12 C11 132.2(2) . . . . ? C8 Ru1 C12 C11 102.82(17) . . . . ? C9 Ru1 C12 C11 65.10(16) . . . . ? C10 Ru1 C12 C11 29.87(16) . . . . ? P1 Ru1 C12 C11 -142.89(15) . . . . ? Cl1 Ru1 C12 C11 132.42(18) . . . . ? Cl2 Ru1 C12 C11 -56.02(17) . . . . ? C8 Ru1 C12 C7 -29.39(15) . . . . ? C11 Ru1 C12 C7 -132.2(2) . . . . ? C9 Ru1 C12 C7 -67.11(15) . . . . ? C10 Ru1 C12 C7 -102.34(17) . . . . ? P1 Ru1 C12 C7 84.90(14) . . . . ? Cl1 Ru1 C12 C7 0.2(3) . . . . ? Cl2 Ru1 C12 C7 171.77(12) . . . . ? C16 N4 C13 O1 -178.9(3) . . . . ? C17 N4 C13 O1 -3.6(4) . . . . ? C16 N4 C13 C14 -0.7(3) . . . . ? C17 N4 C13 C14 174.7(2) . . . . ? O1 C13 C14 C15 -179.8(3) . . . . ? N4 C13 C14 C15 2.0(3) . . . . ? C13 C14 C15 C16 -2.5(3) . . . . ? C13 N4 C16 O2 179.9(3) . . . . ? C17 N4 C16 O2 4.5(4) . . . . ? C13 N4 C16 C15 -0.8(3) . . . . ? C17 N4 C16 C15 -176.2(2) . . . . ? C14 C15 C16 O2 -178.6(3) . . . . ? C14 C15 C16 N4 2.1(3) . . . . ? C16 N4 C17 C8 80.7(3) . . . . ? C13 N4 C17 C8 -94.0(3) . . . . ? C7 C8 C17 N4 -96.2(3) . . . . ? C9 C8 C17 N4 83.3(3) . . . . ? Ru1 C8 C17 N4 175.49(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.633 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.091