# Supplementary Material (ESI) for Metallomics # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Metallomics _journal_coden_cambridge 1400 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Department of Chemistry, Temple Hall 456, Missouri State University, Springfield, MO 65897, USA. ; _publ_contact_author_email NNGerasimchuk@missouristate.edu _publ_contact_author_fax '1 417 836 5507' _publ_contact_author_phone '1 417 836 5165' _publ_contact_author_name 'Prof. Nikolay Gerasimchuk' _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. ; loop_ _publ_author_name 'Floyd Beckford' 'Nikolay Gerasimchuk' data_sq-centro-5 _database_code_depnum_ccdc_archive 'CCDC 797492' #TrackingRef '2919_web_deposit_cif_file_0_NikolayGerasimchuk_1287623765.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Ru(II)-monoarene-thiosemicarbazide complex ; _chemical_name_common 'FAB 302' _chemical_melting_point ? _chemical_formula_moiety 'C28 H31 Cl N3 Ru S, Cl' _chemical_compound_source 'synthesized new Ru(II) complex' _chemical_formula_sum 'C28 H31 Cl2 N3 Ru S' _chemical_formula_weight 613.59 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' 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9976(7) _cell_length_b 11.9803(7) _cell_length_c 12.8925(8) _cell_angle_alpha 82.6790(10) _cell_angle_beta 79.5180(10) _cell_angle_gamma 73.7410(10) _cell_volume 1598.22(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 791 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 54.25 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.742 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8856 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _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 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19364 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _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 1.61 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7843 _reflns_number_gt 6839 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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. There was badly distorted solvent molecule in the structure. Since this complex was crystallized from CH2Cl2, it was possible to identify carbon and chlorine atoms. However, a successfull modeling of disorder was not possible, unfortunately. Therefore, SQUEEZ program (by PLATON) was used to remove electron density that corresponded to the solvent. PLATON SQUEEZ analysis indicated that the solvent accessible volume in the structure is ~350 A(3), which may accomodate ~6 molecules of CH2Cl2 solvent if it would be tightly packed. Below present the output from SQUEEZ program from the *.sqf file. loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 -0.088 0.500 354 79 ' ' _platon_squeeze_details ; _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^)+(0.0395P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7843 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0659 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.003 _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 C1 C 0.9459(2) 0.2636(2) 0.2994(2) 0.0806(7) Uani 1 1 d . . . H1A H 0.8990 0.3126 0.3547 0.121 Uiso 1 1 calc R . . H1B H 1.0257 0.2827 0.2732 0.121 Uiso 1 1 calc R . . H1C H 0.9624 0.1834 0.3269 0.121 Uiso 1 1 calc R . . C2 C 0.86913(18) 0.28262(15) 0.21155(17) 0.0571(5) Uani 1 1 d . . . H2A H 0.9178 0.2344 0.1552 0.068 Uiso 1 1 calc R . . H2B H 0.7911 0.2585 0.2372 0.068 Uiso 1 1 calc R . . C3 C 0.72678(15) 0.48140(13) 0.19940(12) 0.0398(3) Uani 1 1 d . . . C4 C 0.60383(16) 0.77715(13) 0.13183(13) 0.0425(3) Uani 1 1 d . . . H4 H 0.6805 0.7846 0.0909 0.051 Uiso 1 1 calc R . . C5 C 0.49237(15) 0.88049(13) 0.13672(12) 0.0399(3) Uani 1 1 d . . . C6 C 0.40920(16) 0.89743(13) 0.06198(13) 0.0423(3) Uani 1 1 d . . . C7 C 0.42695(19) 0.81872(15) -0.01674(14) 0.0522(4) Uani 1 1 d . . . H7 H 0.4975 0.7540 -0.0208 0.063 Uiso 1 1 calc R . . C8 C 0.3432(2) 0.83634(18) -0.08550(17) 0.0681(6) Uani 1 1 d . . . H8 H 0.3571 0.7841 -0.1366 0.082 Uiso 1 1 calc R . . C9 C 0.2351(2) 0.93289(19) -0.08067(18) 0.0726(6) Uani 1 1 d . . . H9 H 0.1773 0.9428 -0.1277 0.087 Uiso 1 1 calc R . . C10 C 0.2142(2) 1.01106(17) -0.00892(18) 0.0644(5) Uani 1 1 d . . . H10 H 0.1429 1.0750 -0.0077 0.077 Uiso 1 1 calc R . . C11 C 0.30014(17) 0.99715(14) 0.06555(14) 0.0475(4) Uani 1 1 d . . . C12 C 0.28261(18) 1.07701(14) 0.13992(16) 0.0528(4) Uani 1 1 d . . . H12 H 0.2122 1.1418 0.1417 0.063 Uiso 1 1 calc R . . C13 C 0.36709(17) 1.06290(14) 0.21158(14) 0.0487(4) Uani 1 1 d . . . C14 C 0.3500(2) 1.14515(17) 0.28778(18) 0.0665(5) Uani 1 1 d . . . H14 H 0.2801 1.2105 0.2900 0.080 Uiso 1 1 calc R . . C15 C 0.4337(2) 1.12960(19) 0.35675(19) 0.0754(6) Uani 1 1 d . . . H15 H 0.4210 1.1842 0.4056 0.091 Uiso 1 1 calc R . . C16 C 0.5405(2) 1.03056(19) 0.35479(17) 0.0687(6) Uani 1 1 d . . . H16 H 0.5977 1.0209 0.4022 0.082 Uiso 1 1 calc R . . C17 C 0.56029(19) 0.94970(16) 0.28465(15) 0.0547(4) Uani 1 1 d . . . H17 H 0.6304 0.8848 0.2852 0.066 Uiso 1 1 calc R . . C18 C 0.47547(16) 0.96258(13) 0.21015(12) 0.0438(4) Uani 1 1 d . . . C19 C 0.2971(2) 0.83265(19) 0.47813(17) 0.0689(6) Uani 1 1 d . . . H19A H 0.3310 0.8937 0.4388 0.103 Uiso 1 1 calc R . . H19B H 0.3497 0.7944 0.5308 0.103 Uiso 1 1 calc R . . H19C H 0.2112 0.8654 0.5119 0.103 Uiso 1 1 calc R . . C20 C 0.29590(16) 0.74576(15) 0.40429(14) 0.0474(4) Uani 1 1 d . . . C21 C 0.31154(16) 0.62579(15) 0.43954(13) 0.0474(4) Uani 1 1 d . . . H21 H 0.3223 0.6008 0.5094 0.057 Uiso 1 1 calc R . . C22 C 0.31092(15) 0.54488(14) 0.37035(13) 0.0443(4) Uani 1 1 d . . . H22 H 0.3183 0.4675 0.3960 0.053 Uiso 1 1 calc R . . C23 C 0.29928(15) 0.57784(14) 0.26180(13) 0.0422(3) Uani 1 1 d . . . C24 C 0.29792(19) 0.48786(16) 0.19011(16) 0.0575(5) Uani 1 1 d . . . H24 H 0.3607 0.4153 0.2087 0.069 Uiso 1 1 calc R . . C25 C 0.1664(3) 0.4644(2) 0.2121(2) 0.0912(8) Uani 1 1 d . . . H25A H 0.1026 0.5352 0.1973 0.137 Uiso 1 1 calc R . . H25B H 0.1487 0.4370 0.2851 0.137 Uiso 1 1 calc R . . H25C H 0.1648 0.4063 0.1679 0.137 Uiso 1 1 calc R . . C26 C 0.3335(3) 0.5220(3) 0.07463(19) 0.1037(10) Uani 1 1 d . . . H26A H 0.2692 0.5892 0.0529 0.156 Uiso 1 1 calc R . . H26B H 0.3391 0.4585 0.0339 0.156 Uiso 1 1 calc R . . H26C H 0.4148 0.5401 0.0633 0.156 Uiso 1 1 calc R . . C27 C 0.28999(15) 0.69570(14) 0.22687(13) 0.0422(3) Uani 1 1 d . . . H27 H 0.2874 0.7195 0.1556 0.051 Uiso 1 1 calc R . . C28 C 0.28451(15) 0.77932(14) 0.29779(13) 0.0443(4) Uani 1 1 d . . . H28 H 0.2732 0.8574 0.2730 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.60385(4) 0.66011(4) 0.41373(3) 0.05018(10) Uani 1 1 d . . . Cl2 Cl 0.93378(5) 0.66866(4) 0.02230(5) 0.07659(17) Uani 1 1 d . . . N1 N 0.83579(14) 0.40467(12) 0.16914(12) 0.0503(3) Uani 1 1 d . . . H1 H 0.8909 0.4279 0.1213 0.060 Uiso 1 1 calc R . . N2 N 0.71536(13) 0.59199(11) 0.16003(11) 0.0428(3) Uani 1 1 d . . . H2 H 0.7801 0.6105 0.1210 0.051 Uiso 1 1 calc R . . N3 N 0.60073(12) 0.67782(10) 0.18089(10) 0.0360(3) Uani 1 1 d . . . Ru1 Ru 0.461235(11) 0.629896(9) 0.304656(9) 0.03411(5) Uani 1 1 d . . . S1 S 0.60196(4) 0.44354(3) 0.28176(3) 0.04351(9) Uani 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 C1 0.0581(12) 0.0784(15) 0.0990(18) 0.0265(13) -0.0235(12) -0.0154(11) C2 0.0481(10) 0.0365(8) 0.0792(13) -0.0069(8) -0.0037(9) -0.0019(7) C3 0.0434(8) 0.0366(8) 0.0376(8) -0.0036(6) -0.0100(6) -0.0050(6) C4 0.0434(8) 0.0374(8) 0.0419(8) 0.0018(6) -0.0014(7) -0.0082(7) C5 0.0427(8) 0.0303(7) 0.0425(8) 0.0040(6) -0.0038(7) -0.0078(6) C6 0.0505(9) 0.0324(7) 0.0433(8) 0.0038(6) -0.0072(7) -0.0126(7) C7 0.0663(12) 0.0401(9) 0.0494(10) -0.0017(7) -0.0104(8) -0.0128(8) C8 0.0948(16) 0.0564(12) 0.0614(12) -0.0048(9) -0.0274(11) -0.0237(11) C9 0.0903(16) 0.0624(13) 0.0772(14) 0.0036(11) -0.0463(13) -0.0225(12) C10 0.0652(12) 0.0466(10) 0.0839(15) 0.0090(10) -0.0321(11) -0.0117(9) C11 0.0515(10) 0.0344(8) 0.0567(10) 0.0051(7) -0.0146(8) -0.0112(7) C12 0.0494(10) 0.0341(8) 0.0684(12) -0.0009(8) -0.0098(9) -0.0017(7) C13 0.0526(10) 0.0358(8) 0.0556(10) -0.0055(7) -0.0049(8) -0.0094(7) C14 0.0764(14) 0.0451(10) 0.0742(14) -0.0174(9) -0.0085(11) -0.0064(10) C15 0.0963(17) 0.0617(13) 0.0729(14) -0.0265(11) -0.0133(13) -0.0190(12) C16 0.0850(15) 0.0670(13) 0.0618(12) -0.0091(10) -0.0258(11) -0.0216(12) C17 0.0616(11) 0.0488(10) 0.0546(10) -0.0015(8) -0.0157(9) -0.0130(8) C18 0.0523(10) 0.0339(8) 0.0447(9) 0.0019(7) -0.0080(7) -0.0123(7) C19 0.0761(14) 0.0700(13) 0.0598(12) -0.0296(10) 0.0083(10) -0.0193(11) C20 0.0439(9) 0.0490(9) 0.0472(9) -0.0106(7) 0.0035(7) -0.0126(7) C21 0.0468(9) 0.0563(10) 0.0370(8) -0.0005(7) -0.0002(7) -0.0155(8) C22 0.0424(8) 0.0408(8) 0.0497(9) 0.0053(7) -0.0074(7) -0.0145(7) C23 0.0395(8) 0.0407(8) 0.0481(9) -0.0019(7) -0.0100(7) -0.0119(7) C24 0.0633(11) 0.0462(10) 0.0697(12) -0.0085(9) -0.0276(10) -0.0128(9) C25 0.0958(19) 0.0883(18) 0.116(2) -0.0088(15) -0.0391(16) -0.0517(15) C26 0.156(3) 0.107(2) 0.0649(15) -0.0374(14) -0.0023(16) -0.057(2) C27 0.0382(8) 0.0425(8) 0.0432(8) 0.0025(7) -0.0090(6) -0.0071(7) C28 0.0395(8) 0.0360(8) 0.0522(9) -0.0022(7) -0.0013(7) -0.0055(6) Cl1 0.0595(3) 0.0516(2) 0.0450(2) -0.00013(17) -0.01956(19) -0.01794(19) Cl2 0.0547(3) 0.0502(3) 0.1066(4) 0.0003(3) 0.0185(3) -0.0067(2) N1 0.0451(8) 0.0408(7) 0.0558(8) -0.0023(6) -0.0025(6) -0.0007(6) N2 0.0385(7) 0.0366(7) 0.0450(7) 0.0020(5) -0.0001(6) -0.0030(5) N3 0.0391(7) 0.0319(6) 0.0347(6) -0.0020(5) -0.0075(5) -0.0049(5) Ru1 0.03769(7) 0.03121(7) 0.03257(7) -0.00102(4) -0.00613(5) -0.00789(5) S1 0.0452(2) 0.03187(18) 0.0498(2) -0.00009(16) -0.00521(17) -0.00690(16) _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 C1 C2 1.491(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.463(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.318(2) . ? C3 N2 1.3369(19) . ? C3 S1 1.7069(17) . ? C4 N3 1.2807(19) . ? C4 C5 1.477(2) . ? C4 H4 0.9300 . ? C5 C18 1.403(2) . ? C5 C6 1.405(2) . ? C6 C7 1.423(2) . ? C6 C11 1.435(2) . ? C7 C8 1.349(3) . ? C7 H7 0.9300 . ? C8 C9 1.406(3) . ? C8 H8 0.9300 . ? C9 C10 1.345(3) . ? C9 H9 0.9300 . ? C10 C11 1.430(3) . ? C10 H10 0.9300 . ? C11 C12 1.391(3) . ? C12 C13 1.389(3) . ? C12 H12 0.9300 . ? C13 C14 1.431(3) . ? C13 C18 1.436(2) . ? C14 C15 1.354(3) . ? C14 H14 0.9300 . ? C15 C16 1.416(3) . ? C15 H15 0.9300 . ? C16 C17 1.355(3) . ? C16 H16 0.9300 . ? C17 C18 1.423(2) . ? C17 H17 0.9300 . ? C19 C20 1.501(2) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C28 1.399(2) . ? C20 C21 1.423(2) . ? C20 Ru1 2.2526(16) . ? C21 C22 1.401(2) . ? C21 Ru1 2.1723(16) . ? C21 H21 0.9300 . ? C22 C23 1.424(2) . ? C22 Ru1 2.1682(16) . ? C22 H22 0.9300 . ? C23 C27 1.407(2) . ? C23 C24 1.512(2) . ? C23 Ru1 2.2213(15) . ? C24 C26 1.503(3) . ? C24 C25 1.520(3) . ? C24 H24 0.9800 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.422(2) . ? C27 Ru1 2.1973(16) . ? C27 H27 0.9300 . ? C28 Ru1 2.2503(16) . ? C28 H28 0.9300 . ? Cl1 Ru1 2.4122(4) . ? N1 H1 0.8600 . ? N2 N3 1.3929(17) . ? N2 H2 0.8600 . ? N3 Ru1 2.1444(12) . ? Ru1 S1 2.3524(4) . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C1 112.22(17) . . ? N1 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N1 C3 N2 117.05(15) . . ? N1 C3 S1 122.66(12) . . ? N2 C3 S1 120.25(12) . . ? N3 C4 C5 123.58(14) . . ? N3 C4 H4 118.2 . . ? C5 C4 H4 118.2 . . ? C18 C5 C6 121.38(14) . . ? C18 C5 C4 120.35(15) . . ? C6 C5 C4 118.16(14) . . ? C5 C6 C7 122.86(15) . . ? C5 C6 C11 119.03(15) . . ? C7 C6 C11 118.10(16) . . ? C8 C7 C6 121.16(18) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 120.68(19) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 120.8(2) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.90(19) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 122.51(17) . . ? C12 C11 C6 119.18(16) . . ? C10 C11 C6 118.31(17) . . ? C13 C12 C11 122.02(16) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 122.24(17) . . ? C12 C13 C18 119.45(15) . . ? C14 C13 C18 118.30(17) . . ? C15 C14 C13 121.19(19) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 120.2(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 120.8(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 121.05(18) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C5 C18 C17 122.72(15) . . ? C5 C18 C13 118.84(15) . . ? C17 C18 C13 118.43(15) . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C28 C20 C21 117.92(15) . . ? C28 C20 C19 121.06(17) . . ? C21 C20 C19 120.97(17) . . ? C28 C20 Ru1 71.81(9) . . ? C21 C20 Ru1 68.20(9) . . ? C19 C20 Ru1 129.39(13) . . ? C22 C21 C20 120.82(15) . . ? C22 C21 Ru1 71.02(9) . . ? C20 C21 Ru1 74.33(9) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? Ru1 C21 H21 127.1 . . ? C21 C22 C23 121.81(15) . . ? C21 C22 Ru1 71.33(9) . . ? C23 C22 Ru1 73.11(9) . . ? C21 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? Ru1 C22 H22 128.9 . . ? C27 C23 C22 116.73(14) . . ? C27 C23 C24 123.22(15) . . ? C22 C23 C24 120.05(15) . . ? C27 C23 Ru1 70.50(9) . . ? C22 C23 Ru1 69.07(9) . . ? C24 C23 Ru1 130.94(12) . . ? C26 C24 C23 113.44(17) . . ? C26 C24 C25 111.0(2) . . ? C23 C24 C25 108.69(18) . . ? C26 C24 H24 107.8 . . ? C23 C24 H24 107.8 . . ? C25 C24 H24 107.8 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 C28 121.68(15) . . ? C23 C27 Ru1 72.36(9) . . ? C28 C27 Ru1 73.38(9) . . ? C23 C27 H27 119.2 . . ? C28 C27 H27 119.2 . . ? Ru1 C27 H27 127.2 . . ? C20 C28 C27 120.89(15) . . ? C20 C28 Ru1 72.00(10) . . ? C27 C28 Ru1 69.34(9) . . ? C20 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? Ru1 C28 H28 132.1 . . ? C3 N1 C2 124.31(15) . . ? C3 N1 H1 117.8 . . ? C2 N1 H1 117.8 . . ? C3 N2 N3 121.38(13) . . ? C3 N2 H2 119.3 . . ? N3 N2 H2 119.3 . . ? C4 N3 N2 113.28(13) . . ? C4 N3 Ru1 130.58(11) . . ? N2 N3 Ru1 115.42(9) . . ? N3 Ru1 C22 154.32(6) . . ? N3 Ru1 C21 165.71(6) . . ? C22 Ru1 C21 37.65(6) . . ? N3 Ru1 C27 99.37(5) . . ? C22 Ru1 C27 67.02(6) . . ? C21 Ru1 C27 79.55(6) . . ? N3 Ru1 C23 119.06(5) . . ? C22 Ru1 C23 37.83(6) . . ? C21 Ru1 C23 68.33(6) . . ? C27 Ru1 C23 37.14(6) . . ? N3 Ru1 C28 104.24(5) . . ? C22 Ru1 C28 78.51(6) . . ? C21 Ru1 C28 66.26(6) . . ? C27 Ru1 C28 37.28(6) . . ? C23 Ru1 C28 67.09(6) . . ? N3 Ru1 C20 129.00(5) . . ? C22 Ru1 C20 67.46(6) . . ? C21 Ru1 C20 37.47(6) . . ? C27 Ru1 C20 66.92(6) . . ? C23 Ru1 C20 80.16(6) . . ? C28 Ru1 C20 36.19(6) . . ? N3 Ru1 S1 81.40(3) . . ? C22 Ru1 S1 87.95(5) . . ? C21 Ru1 S1 111.33(5) . . ? C27 Ru1 S1 122.61(4) . . ? C23 Ru1 S1 92.60(4) . . ? C28 Ru1 S1 159.26(5) . . ? C20 Ru1 S1 148.38(5) . . ? N3 Ru1 Cl1 81.73(3) . . ? C22 Ru1 Cl1 121.21(5) . . ? C21 Ru1 Cl1 92.15(5) . . ? C27 Ru1 Cl1 150.13(4) . . ? C23 Ru1 Cl1 158.96(4) . . ? C28 Ru1 Cl1 113.23(5) . . ? C20 Ru1 Cl1 89.03(5) . . ? S1 Ru1 Cl1 87.186(16) . . ? C3 S1 Ru1 99.69(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 N3 C4 C5 C18 94.5(2) . . . . ? N3 C4 C5 C6 -89.3(2) . . . . ? C18 C5 C6 C7 177.00(15) . . . . ? C4 C5 C6 C7 0.9(2) . . . . ? C18 C5 C6 C11 -4.0(2) . . . . ? C4 C5 C6 C11 179.84(14) . . . . ? C5 C6 C7 C8 178.28(17) . . . . ? C11 C6 C7 C8 -0.7(3) . . . . ? C6 C7 C8 C9 -0.5(3) . . . . ? C7 C8 C9 C10 1.4(4) . . . . ? C8 C9 C10 C11 -1.0(3) . . . . ? C9 C10 C11 C12 179.1(2) . . . . ? C9 C10 C11 C6 -0.1(3) . . . . ? C5 C6 C11 C12 2.7(2) . . . . ? C7 C6 C11 C12 -178.28(16) . . . . ? C5 C6 C11 C10 -178.02(16) . . . . ? C7 C6 C11 C10 1.0(2) . . . . ? C10 C11 C12 C13 -179.67(18) . . . . ? C6 C11 C12 C13 -0.4(3) . . . . ? C11 C12 C13 C14 179.59(18) . . . . ? C11 C12 C13 C18 -0.6(3) . . . . ? C12 C13 C14 C15 -179.9(2) . . . . ? C18 C13 C14 C15 0.2(3) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C14 C15 C16 C17 -0.4(4) . . . . ? C15 C16 C17 C18 0.8(3) . . . . ? C6 C5 C18 C17 -178.01(16) . . . . ? C4 C5 C18 C17 -2.0(2) . . . . ? C6 C5 C18 C13 3.0(2) . . . . ? C4 C5 C18 C13 179.05(14) . . . . ? C16 C17 C18 C5 -179.64(18) . . . . ? C16 C17 C18 C13 -0.7(3) . . . . ? C12 C13 C18 C5 -0.7(2) . . . . ? C14 C13 C18 C5 179.17(16) . . . . ? C12 C13 C18 C17 -179.68(16) . . . . ? C14 C13 C18 C17 0.2(2) . . . . ? C28 C20 C21 C22 -2.2(2) . . . . ? C19 C20 C21 C22 -179.74(17) . . . . ? Ru1 C20 C21 C22 -55.89(14) . . . . ? C28 C20 C21 Ru1 53.67(14) . . . . ? C19 C20 C21 Ru1 -123.86(17) . . . . ? C20 C21 C22 C23 2.2(3) . . . . ? Ru1 C21 C22 C23 -55.22(14) . . . . ? C20 C21 C22 Ru1 57.46(15) . . . . ? C21 C22 C23 C27 0.8(2) . . . . ? Ru1 C22 C23 C27 -53.65(13) . . . . ? C21 C22 C23 C24 -179.48(16) . . . . ? Ru1 C22 C23 C24 126.10(15) . . . . ? C21 C22 C23 Ru1 54.42(15) . . . . ? C27 C23 C24 C26 20.9(3) . . . . ? C22 C23 C24 C26 -158.8(2) . . . . ? Ru1 C23 C24 C26 -71.4(2) . . . . ? C27 C23 C24 C25 -103.1(2) . . . . ? C22 C23 C24 C25 77.2(2) . . . . ? Ru1 C23 C24 C25 164.61(16) . . . . ? C22 C23 C27 C28 -3.8(2) . . . . ? C24 C23 C27 C28 176.49(16) . . . . ? Ru1 C23 C27 C28 -56.71(14) . . . . ? C22 C23 C27 Ru1 52.94(13) . . . . ? C24 C23 C27 Ru1 -126.80(16) . . . . ? C21 C20 C28 C27 -0.7(2) . . . . ? C19 C20 C28 C27 176.78(16) . . . . ? Ru1 C20 C28 C27 51.19(14) . . . . ? C21 C20 C28 Ru1 -51.94(14) . . . . ? C19 C20 C28 Ru1 125.59(17) . . . . ? C23 C27 C28 C20 3.9(2) . . . . ? Ru1 C27 C28 C20 -52.37(14) . . . . ? C23 C27 C28 Ru1 56.23(14) . . . . ? N2 C3 N1 C2 174.18(15) . . . . ? S1 C3 N1 C2 -7.8(2) . . . . ? C1 C2 N1 C3 -95.0(2) . . . . ? N1 C3 N2 N3 175.15(14) . . . . ? S1 C3 N2 N3 -2.9(2) . . . . ? C5 C4 N3 N2 176.87(15) . . . . ? C5 C4 N3 Ru1 -13.5(2) . . . . ? C3 N2 N3 C4 -175.87(14) . . . . ? C3 N2 N3 Ru1 12.80(18) . . . . ? C4 N3 Ru1 C22 111.20(17) . . . . ? N2 N3 Ru1 C22 -79.31(16) . . . . ? C4 N3 Ru1 C21 -28.5(3) . . . . ? N2 N3 Ru1 C21 141.0(2) . . . . ? C4 N3 Ru1 C27 55.93(15) . . . . ? N2 N3 Ru1 C27 -134.58(10) . . . . ? C4 N3 Ru1 C23 89.57(15) . . . . ? N2 N3 Ru1 C23 -100.94(11) . . . . ? C4 N3 Ru1 C28 18.14(15) . . . . ? N2 N3 Ru1 C28 -172.37(10) . . . . ? C4 N3 Ru1 C20 -11.88(17) . . . . ? N2 N3 Ru1 C20 157.61(10) . . . . ? C4 N3 Ru1 S1 177.77(14) . . . . ? N2 N3 Ru1 S1 -12.74(10) . . . . ? C4 N3 Ru1 Cl1 -93.85(14) . . . . ? N2 N3 Ru1 Cl1 75.64(10) . . . . ? C21 C22 Ru1 N3 -164.85(11) . . . . ? C23 C22 Ru1 N3 -31.70(17) . . . . ? C23 C22 Ru1 C21 133.15(15) . . . . ? C21 C22 Ru1 C27 -103.12(11) . . . . ? C23 C22 Ru1 C27 30.03(9) . . . . ? C21 C22 Ru1 C23 -133.15(15) . . . . ? C21 C22 Ru1 C28 -65.85(10) . . . . ? C23 C22 Ru1 C28 67.30(10) . . . . ? C21 C22 Ru1 C20 -29.69(10) . . . . ? C23 C22 Ru1 C20 103.47(11) . . . . ? C21 C22 Ru1 S1 129.95(10) . . . . ? C23 C22 Ru1 S1 -96.90(9) . . . . ? C21 C22 Ru1 Cl1 44.48(11) . . . . ? C23 C22 Ru1 Cl1 177.64(8) . . . . ? C22 C21 Ru1 N3 152.69(19) . . . . ? C20 C21 Ru1 N3 21.4(3) . . . . ? C20 C21 Ru1 C22 -131.25(15) . . . . ? C22 C21 Ru1 C27 65.75(10) . . . . ? C20 C21 Ru1 C27 -65.50(10) . . . . ? C22 C21 Ru1 C23 28.78(10) . . . . ? C20 C21 Ru1 C23 -102.47(11) . . . . ? C22 C21 Ru1 C28 102.34(11) . . . . ? C20 C21 Ru1 C28 -28.90(10) . . . . ? C22 C21 Ru1 C20 131.25(15) . . . . ? C22 C21 Ru1 S1 -55.33(10) . . . . ? C20 C21 Ru1 S1 173.42(9) . . . . ? C22 C21 Ru1 Cl1 -143.15(9) . . . . ? C20 C21 Ru1 Cl1 85.60(10) . . . . ? C23 C27 Ru1 N3 126.69(9) . . . . ? C28 C27 Ru1 N3 -101.24(9) . . . . ? C23 C27 Ru1 C22 -30.55(9) . . . . ? C28 C27 Ru1 C22 101.52(11) . . . . ? C23 C27 Ru1 C21 -67.77(10) . . . . ? C28 C27 Ru1 C21 64.30(10) . . . . ? C28 C27 Ru1 C23 132.07(14) . . . . ? C23 C27 Ru1 C28 -132.07(14) . . . . ? C23 C27 Ru1 C20 -104.77(11) . . . . ? C28 C27 Ru1 C20 27.30(9) . . . . ? C23 C27 Ru1 S1 40.95(10) . . . . ? C28 C27 Ru1 S1 173.02(7) . . . . ? C23 C27 Ru1 Cl1 -143.62(9) . . . . ? C28 C27 Ru1 Cl1 -11.55(15) . . . . ? C27 C23 Ru1 N3 -64.84(10) . . . . ? C22 C23 Ru1 N3 164.90(9) . . . . ? C24 C23 Ru1 N3 52.69(17) . . . . ? C27 C23 Ru1 C22 130.26(14) . . . . ? C24 C23 Ru1 C22 -112.21(19) . . . . ? C27 C23 Ru1 C21 101.61(11) . . . . ? C22 C23 Ru1 C21 -28.65(10) . . . . ? C24 C23 Ru1 C21 -140.86(17) . . . . ? C22 C23 Ru1 C27 -130.26(14) . . . . ? C24 C23 Ru1 C27 117.53(19) . . . . ? C27 C23 Ru1 C28 29.21(9) . . . . ? C22 C23 Ru1 C28 -101.05(11) . . . . ? C24 C23 Ru1 C28 146.74(17) . . . . ? C27 C23 Ru1 C20 64.53(10) . . . . ? C22 C23 Ru1 C20 -65.73(10) . . . . ? C24 C23 Ru1 C20 -177.94(17) . . . . ? C27 C23 Ru1 S1 -146.45(9) . . . . ? C22 C23 Ru1 S1 83.29(9) . . . . ? C24 C23 Ru1 S1 -28.92(15) . . . . ? C27 C23 Ru1 Cl1 124.62(12) . . . . ? C22 C23 Ru1 Cl1 -5.64(18) . . . . ? C24 C23 Ru1 Cl1 -117.85(16) . . . . ? C20 C28 Ru1 N3 -138.83(10) . . . . ? C27 C28 Ru1 N3 86.78(10) . . . . ? C20 C28 Ru1 C22 67.37(10) . . . . ? C27 C28 Ru1 C22 -67.01(10) . . . . ? C20 C28 Ru1 C21 29.86(10) . . . . ? C27 C28 Ru1 C21 -104.52(11) . . . . ? C20 C28 Ru1 C27 134.38(15) . . . . ? C20 C28 Ru1 C23 105.27(11) . . . . ? C27 C28 Ru1 C23 -29.12(9) . . . . ? C27 C28 Ru1 C20 -134.38(15) . . . . ? C20 C28 Ru1 S1 117.59(13) . . . . ? C27 C28 Ru1 S1 -16.80(18) . . . . ? C20 C28 Ru1 Cl1 -51.84(10) . . . . ? C27 C28 Ru1 Cl1 173.77(8) . . . . ? C28 C20 Ru1 N3 55.19(12) . . . . ? C21 C20 Ru1 N3 -173.33(9) . . . . ? C19 C20 Ru1 N3 -60.5(2) . . . . ? C28 C20 Ru1 C22 -101.66(11) . . . . ? C21 C20 Ru1 C22 29.82(10) . . . . ? C19 C20 Ru1 C22 142.69(19) . . . . ? C28 C20 Ru1 C21 -131.48(15) . . . . ? C19 C20 Ru1 C21 112.9(2) . . . . ? C28 C20 Ru1 C27 -28.07(10) . . . . ? C21 C20 Ru1 C27 103.41(11) . . . . ? C19 C20 Ru1 C27 -143.72(19) . . . . ? C28 C20 Ru1 C23 -64.41(10) . . . . ? C21 C20 Ru1 C23 67.07(10) . . . . ? C19 C20 Ru1 C23 179.94(19) . . . . ? C21 C20 Ru1 C28 131.48(15) . . . . ? C19 C20 Ru1 C28 -115.7(2) . . . . ? C28 C20 Ru1 S1 -143.23(9) . . . . ? C21 C20 Ru1 S1 -11.75(15) . . . . ? C19 C20 Ru1 S1 101.12(18) . . . . ? C28 C20 Ru1 Cl1 133.73(9) . . . . ? C21 C20 Ru1 Cl1 -94.80(10) . . . . ? C19 C20 Ru1 Cl1 18.07(17) . . . . ? N1 C3 S1 Ru1 175.15(13) . . . . ? N2 C3 S1 Ru1 -6.93(13) . . . . ? N3 Ru1 S1 C3 9.40(6) . . . . ? C22 Ru1 S1 C3 165.96(7) . . . . ? C21 Ru1 S1 C3 -163.86(7) . . . . ? C27 Ru1 S1 C3 105.07(7) . . . . ? C23 Ru1 S1 C3 128.41(7) . . . . ? C28 Ru1 S1 C3 117.07(13) . . . . ? C20 Ru1 S1 C3 -156.22(10) . . . . ? Cl1 Ru1 S1 C3 -72.65(5) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.517 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.048