# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_kyo11 _database_code_depnum_ccdc_archive 'CCDC 875411' #TrackingRef 'web_deposit_cif_file_0_TomoyaIshizuka_1333779144.RuOH2N4Py.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24.50 H25 Cl3 F12 N5 O P2 Ru' _chemical_formula_weight 902.85 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' F F 0.0171 0.0103 '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' Ru Ru -1.2594 0.8363 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.3277(18) _cell_length_b 18.234(3) _cell_length_c 15.932(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.573(2) _cell_angle_gamma 90.00 _cell_volume 3262.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8367 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14262 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 24.29 _reflns_number_total 5258 _reflns_number_gt 3975 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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/[?^2^(Fo^2^)+(0.0683P)^2^+9.6866P] 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 5258 _refine_ls_number_parameters 492 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1407 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 N1 N -0.3465(4) 0.3233(3) -0.0977(2) 0.0275(10) Uani 1 1 d . . . N2 N -0.5625(4) 0.2788(2) -0.0749(3) 0.0296(10) Uani 1 1 d . . . N3 N -0.4447(4) 0.2238(3) -0.2049(3) 0.0306(11) Uani 1 1 d . . . N4 N -0.2291(4) 0.1957(3) -0.0821(3) 0.0301(10) Uani 1 1 d . . . N5 N -0.3520(4) 0.2525(3) 0.0491(3) 0.0315(11) Uani 1 1 d . . . C1 C -0.6582(5) 0.2663(3) -0.0362(4) 0.0342(14) Uani 1 1 d . . . H1 H -0.6608 0.2229 -0.0035 0.041 Uiso 1 1 calc R . . C2 C -0.7527(5) 0.3137(4) -0.0418(4) 0.0400(15) Uani 1 1 d . . . H2 H -0.8192 0.3030 -0.0132 0.048 Uiso 1 1 calc R . . C3 C -0.7509(5) 0.3760(4) -0.0882(4) 0.0446(16) Uani 1 1 d . . . H3 H -0.8168 0.4087 -0.0933 0.054 Uiso 1 1 calc R . . C4 C -0.6528(5) 0.3915(3) -0.1279(4) 0.0413(15) Uani 1 1 d . . . H4 H -0.6492 0.4353 -0.1598 0.050 Uiso 1 1 calc R . . C5 C -0.5602(5) 0.3421(3) -0.1201(3) 0.0326(13) Uani 1 1 d . . . C6 C -0.4499(5) 0.3498(3) -0.1634(3) 0.0321(13) Uani 1 1 d . . . H5 H -0.4380 0.4009 -0.1834 0.039 Uiso 1 1 calc R . . C7 C -0.4603(5) 0.2941(3) -0.2346(3) 0.0317(13) Uani 1 1 d . . . C8 C -0.4845(5) 0.3110(4) -0.3181(4) 0.0392(14) Uani 1 1 d . . . H6 H -0.4936 0.3606 -0.3362 0.047 Uiso 1 1 calc R . . C9 C -0.4956(6) 0.2540(4) -0.3763(4) 0.0466(17) Uani 1 1 d . . . H7 H -0.5143 0.2638 -0.4351 0.056 Uiso 1 1 calc R . . C10 C -0.4794(5) 0.1839(4) -0.3481(4) 0.0428(16) Uani 1 1 d . . . H8 H -0.4850 0.1446 -0.3876 0.051 Uiso 1 1 calc R . . C11 C -0.4549(5) 0.1695(4) -0.2625(4) 0.0385(14) Uani 1 1 d . . . H9 H -0.4449 0.1202 -0.2439 0.046 Uiso 1 1 calc R . . C12 C -0.2312(5) 0.3213(3) -0.1359(4) 0.0339(13) Uani 1 1 d . . . H10 H -0.2483 0.3230 -0.1984 0.041 Uiso 1 1 calc R . . H11 H -0.1817 0.3644 -0.1167 0.041 Uiso 1 1 calc R . . C13 C -0.1651(5) 0.2520(3) -0.1088(3) 0.0297(12) Uani 1 1 d . . . C14 C -0.0447(5) 0.2445(4) -0.1161(4) 0.0390(15) Uani 1 1 d . . . H12 H -0.0010 0.2845 -0.1346 0.047 Uiso 1 1 calc R . . C15 C 0.0099(6) 0.1788(4) -0.0964(4) 0.0463(17) Uani 1 1 d . . . H13 H 0.0917 0.1722 -0.1019 0.056 Uiso 1 1 calc R . . C16 C -0.0548(6) 0.1226(4) -0.0686(4) 0.0465(16) Uani 1 1 d . . . H14 H -0.0179 0.0767 -0.0541 0.056 Uiso 1 1 calc R . . C17 C -0.1740(5) 0.1326(3) -0.0618(4) 0.0360(14) Uani 1 1 d . . . H15 H -0.2179 0.0933 -0.0420 0.043 Uiso 1 1 calc R . . C18 C -0.3339(5) 0.3712(3) -0.0198(3) 0.0329(13) Uani 1 1 d . . . H16 H -0.4059 0.4020 -0.0198 0.040 Uiso 1 1 calc R . . H17 H -0.2643 0.4041 -0.0199 0.040 Uiso 1 1 calc R . . C19 C -0.3173(5) 0.3235(3) 0.0586(3) 0.0291(12) Uani 1 1 d . . . C20 C -0.2759(5) 0.3526(3) 0.1370(4) 0.0374(14) Uani 1 1 d . . . H18 H -0.2519 0.4025 0.1423 0.045 Uiso 1 1 calc R . . C21 C -0.2698(6) 0.3077(4) 0.2079(4) 0.0424(15) Uani 1 1 d . . . H19 H -0.2412 0.3265 0.2625 0.051 Uiso 1 1 calc R . . C22 C -0.3054(6) 0.2359(3) 0.1982(4) 0.0452(16) Uani 1 1 d . . . H20 H -0.3029 0.2045 0.2460 0.054 Uiso 1 1 calc R . . C23 C -0.3449(5) 0.2102(3) 0.1183(4) 0.0369(14) Uani 1 1 d . . . H21 H -0.3681 0.1602 0.1119 0.044 Uiso 1 1 calc R . . C24 C 0.3730(10) 0.4118(5) 0.1871(6) 0.091(3) Uani 1 1 d . . . H22 H 0.4251 0.4239 0.2402 0.109 Uiso 1 1 calc R . . H23 H 0.2943 0.4345 0.1903 0.109 Uiso 1 1 calc R . . P1 P 0.0000 0.5000 0.0000 0.0371(5) Uani 1 2 d S . . P2 P 0.7411(2) 0.49044(10) 0.35565(15) 0.0637(6) Uani 1 1 d . . . P3 P 0.8142(4) 0.42814(18) 0.6561(2) 0.0386(8) Uani 0.50 1 d P A 2 F1 F -0.0050(3) 0.41608(17) -0.0296(2) 0.0484(9) Uani 1 1 d . . . F2 F -0.1187(3) 0.5165(2) -0.0606(3) 0.0589(11) Uani 1 1 d . . . F3 F 0.0763(3) 0.52053(19) -0.0740(3) 0.0567(11) Uani 1 1 d . . . F4 F 0.6345(4) 0.4598(2) 0.2902(4) 0.0944(17) Uani 1 1 d . . . F5 F 0.7156(6) 0.5698(3) 0.3229(5) 0.144(3) Uani 1 1 d . . . F6 F 0.8293(5) 0.4750(3) 0.2914(3) 0.1053(19) Uani 1 1 d . . . F7 F 0.7623(5) 0.4102(2) 0.3923(3) 0.0845(15) Uani 1 1 d . . . F8 F 0.6503(6) 0.5035(4) 0.4228(5) 0.144(3) Uani 1 1 d . . . F9 F 0.8491(4) 0.5199(2) 0.4223(3) 0.0752(13) Uani 1 1 d . . . F17 F 0.7114(9) 0.4486(5) 0.5864(5) 0.077(3) Uani 0.50 1 d P A 2 F18 F 0.9042(8) 0.4169(6) 0.5889(5) 0.075(3) Uani 0.50 1 d P . . F19 F 0.8483(9) 0.5109(5) 0.6657(6) 0.070(3) Uani 0.50 1 d P A 2 F22 F 0.9191(8) 0.4082(7) 0.7302(5) 0.071(3) Uani 0.50 1 d P A 2 Ru1 Ru -0.40372(4) 0.22418(2) -0.07549(3) 0.02644(16) Uani 1 1 d . . . Cl1 Cl 0.43375(15) 0.45022(9) 0.10214(11) 0.0506(4) Uani 1 1 d . . . Cl2 Cl 0.3559(2) 0.31840(13) 0.18058(12) 0.0852(7) Uani 1 1 d . . . O1 O -0.4705(4) 0.1146(3) -0.0564(3) 0.0504(12) Uani 1 1 d . . . H24 H -0.554(8) 0.105(4) -0.085(5) 0.08(3) Uiso 1 1 d . . . F23 F 0.7751(8) 0.3465(4) 0.6454(7) 0.072(3) Uani 0.50 1 d P A 2 Cl5 Cl 0.8873(11) 0.3561(4) 0.6632(7) 0.197(5) Uani 0.50 1 d P A 1 Cl4 Cl 0.7638(11) 0.4812(5) 0.6964(6) 0.178(4) Uani 0.50 1 d P A 1 F24 F 0.7241(7) 0.4358(4) 0.7258(5) 0.055(2) Uani 0.50 1 d P A 2 C25 C 0.881(3) 0.4477(17) 0.669(4) 0.26(3) Uani 0.50 1 d P A 1 H25 H -0.466(11) 0.078(7) -0.005(8) 0.17(5) 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 N1 0.015(2) 0.053(3) 0.012(2) -0.0112(19) -0.0073(17) 0.006(2) N2 0.022(2) 0.041(3) 0.025(2) -0.005(2) -0.0009(19) -0.001(2) N3 0.020(2) 0.046(3) 0.026(2) -0.006(2) 0.0033(19) -0.002(2) N4 0.028(3) 0.041(3) 0.022(2) -0.008(2) 0.002(2) 0.002(2) N5 0.030(3) 0.040(3) 0.025(3) 0.001(2) 0.005(2) 0.004(2) C1 0.029(3) 0.046(4) 0.028(3) -0.011(3) 0.005(2) -0.006(3) C2 0.023(3) 0.059(4) 0.038(4) -0.017(3) 0.002(3) -0.002(3) C3 0.023(3) 0.057(4) 0.052(4) -0.023(3) -0.003(3) 0.005(3) C4 0.039(4) 0.037(3) 0.044(4) -0.010(3) -0.009(3) 0.002(3) C5 0.032(3) 0.038(3) 0.026(3) -0.009(2) -0.004(2) -0.004(3) C6 0.029(3) 0.038(3) 0.027(3) 0.005(2) -0.004(2) -0.003(3) C7 0.019(3) 0.044(3) 0.032(3) -0.002(3) 0.001(2) -0.001(2) C8 0.037(3) 0.055(4) 0.025(3) 0.007(3) 0.001(3) -0.003(3) C9 0.040(4) 0.075(5) 0.025(3) 0.003(3) 0.005(3) -0.010(3) C10 0.037(4) 0.065(4) 0.027(3) -0.017(3) 0.006(3) -0.012(3) C11 0.028(3) 0.050(4) 0.038(4) -0.010(3) 0.008(3) -0.003(3) C12 0.029(3) 0.047(4) 0.026(3) 0.001(3) 0.001(2) -0.010(3) C13 0.026(3) 0.041(3) 0.020(3) -0.008(2) -0.002(2) -0.003(3) C14 0.032(3) 0.052(4) 0.033(3) -0.015(3) 0.006(3) -0.009(3) C15 0.028(3) 0.063(5) 0.049(4) -0.025(3) 0.007(3) 0.003(3) C16 0.044(4) 0.044(4) 0.050(4) -0.017(3) 0.001(3) 0.010(3) C17 0.035(3) 0.040(3) 0.033(3) -0.010(3) 0.004(3) 0.002(3) C18 0.033(3) 0.029(3) 0.035(3) -0.002(2) -0.001(3) -0.002(3) C19 0.024(3) 0.038(3) 0.024(3) -0.004(2) -0.001(2) 0.008(2) C20 0.030(3) 0.043(3) 0.037(4) -0.008(3) -0.003(3) 0.009(3) C21 0.039(4) 0.058(4) 0.027(3) -0.011(3) -0.005(3) 0.016(3) C22 0.058(4) 0.048(4) 0.028(4) 0.004(3) 0.002(3) 0.023(3) C23 0.041(4) 0.041(3) 0.029(3) 0.001(3) 0.006(3) 0.010(3) C24 0.117(8) 0.091(7) 0.070(6) -0.009(5) 0.031(6) -0.035(6) P1 0.0243(11) 0.0241(10) 0.0647(16) -0.0008(10) 0.0127(11) -0.0012(9) P2 0.0643(13) 0.0354(10) 0.0835(15) -0.0129(9) -0.0198(12) 0.0038(9) P3 0.045(2) 0.0290(18) 0.045(2) 0.0044(14) 0.0199(17) -0.0006(17) F1 0.046(2) 0.0261(17) 0.075(3) -0.0060(16) 0.0150(19) -0.0027(16) F2 0.036(2) 0.049(2) 0.089(3) 0.000(2) -0.003(2) 0.0049(18) F3 0.057(2) 0.038(2) 0.082(3) 0.0033(18) 0.035(2) 0.0022(18) F4 0.082(3) 0.060(3) 0.124(4) -0.022(3) -0.049(3) 0.004(3) F5 0.157(6) 0.043(3) 0.200(7) -0.001(3) -0.101(5) -0.003(3) F6 0.098(4) 0.131(5) 0.088(4) -0.031(3) 0.019(3) -0.051(4) F7 0.099(4) 0.051(3) 0.091(4) 0.001(2) -0.030(3) -0.016(3) F8 0.108(5) 0.139(6) 0.193(7) -0.101(5) 0.051(5) -0.030(4) F9 0.082(3) 0.042(2) 0.092(3) -0.015(2) -0.026(3) -0.005(2) F17 0.102(7) 0.072(6) 0.054(5) 0.000(4) 0.001(5) -0.012(5) F18 0.065(6) 0.107(7) 0.062(6) 0.007(5) 0.044(5) 0.001(5) F19 0.091(7) 0.042(5) 0.078(6) 0.014(4) 0.015(5) -0.017(5) F22 0.054(5) 0.108(8) 0.049(5) 0.011(5) 0.002(4) 0.014(6) Ru1 0.0244(3) 0.0321(3) 0.0227(3) -0.00252(18) 0.00254(18) -0.0018(2) Cl1 0.0517(10) 0.0462(9) 0.0530(10) 0.0035(7) 0.0036(8) 0.0000(8) Cl2 0.123(2) 0.0808(15) 0.0482(12) 0.0153(10) -0.0045(12) -0.0340(14) O1 0.045(3) 0.050(3) 0.054(3) 0.002(2) -0.003(2) -0.010(2) F23 0.070(6) 0.040(5) 0.119(8) -0.023(5) 0.062(6) -0.006(4) Cl5 0.296(13) 0.092(4) 0.253(11) 0.031(6) 0.219(11) 0.064(7) Cl4 0.275(12) 0.107(6) 0.169(8) 0.046(5) 0.090(8) 0.095(7) F24 0.058(5) 0.046(5) 0.063(5) 0.012(4) 0.023(4) 0.011(4) C25 0.11(2) 0.10(2) 0.61(9) 0.14(4) 0.22(4) 0.053(19) _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 N1 C18 1.509(7) . ? N1 C12 1.513(6) . ? N1 C6 1.542(7) . ? N1 Ru1 1.967(5) . ? N2 C1 1.336(7) . ? N2 C5 1.362(7) . ? N2 Ru1 2.057(4) . ? N3 C11 1.344(7) . ? N3 C7 1.370(7) . ? N3 Ru1 2.052(4) . ? N4 C17 1.329(7) . ? N4 C13 1.356(7) . ? N4 Ru1 2.061(4) . ? N5 C23 1.341(7) . ? N5 C19 1.356(7) . ? N5 Ru1 2.060(5) . ? C1 C2 1.369(8) . ? C2 C3 1.358(9) . ? C3 C4 1.378(9) . ? C4 C5 1.376(8) . ? C5 C6 1.510(8) . ? C6 C7 1.517(8) . ? C7 C8 1.359(8) . ? C8 C9 1.387(9) . ? C9 C10 1.359(9) . ? C10 C11 1.381(8) . ? C12 C13 1.502(8) . ? C13 C14 1.391(8) . ? C14 C15 1.366(9) . ? C15 C16 1.366(9) . ? C16 C17 1.381(8) . ? C18 C19 1.512(8) . ? C19 C20 1.381(8) . ? C20 C21 1.391(9) . ? C21 C22 1.372(9) . ? C22 C23 1.375(8) . ? C24 Cl2 1.716(9) . ? C24 Cl1 1.744(8) . ? P1 F2 1.577(4) . ? P1 F2 1.577(4) 3_565 ? P1 F3 1.596(3) 3_565 ? P1 F3 1.596(3) . ? P1 F1 1.600(3) . ? P1 F1 1.600(3) 3_565 ? P2 F6 1.548(6) . ? P2 F5 1.553(5) . ? P2 F7 1.581(5) . ? P2 F4 1.589(5) . ? P2 F8 1.597(7) . ? P2 F9 1.603(5) . ? P3 F17 1.545(10) . ? P3 F23 1.555(8) . ? P3 F19 1.560(9) . ? P3 F18 1.587(8) . ? P3 F22 1.602(10) . ? P3 F24 1.610(8) . ? F18 C25 1.45(6) . ? F18 Cl5 1.650(11) . ? Ru1 O1 2.172(5) . ? Cl5 C25 1.68(3) . ? Cl4 C25 1.57(3) . ? 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 C18 N1 C12 110.6(4) . . ? C18 N1 C6 111.0(4) . . ? C12 N1 C6 110.7(4) . . ? C18 N1 Ru1 112.5(3) . . ? C12 N1 Ru1 111.9(3) . . ? C6 N1 Ru1 99.9(3) . . ? C1 N2 C5 117.6(5) . . ? C1 N2 Ru1 133.0(4) . . ? C5 N2 Ru1 109.3(3) . . ? C11 N3 C7 117.1(5) . . ? C11 N3 Ru1 132.6(4) . . ? C7 N3 Ru1 110.2(3) . . ? C17 N4 C13 118.6(5) . . ? C17 N4 Ru1 128.9(4) . . ? C13 N4 Ru1 112.4(4) . . ? C23 N5 C19 118.3(5) . . ? C23 N5 Ru1 128.8(4) . . ? C19 N5 Ru1 112.9(3) . . ? N2 C1 C2 122.5(6) . . ? C3 C2 C1 119.8(6) . . ? C2 C3 C4 119.5(6) . . ? C5 C4 C3 118.4(6) . . ? N2 C5 C4 122.3(5) . . ? N2 C5 C6 113.3(5) . . ? C4 C5 C6 124.4(5) . . ? C5 C6 C7 107.0(4) . . ? C5 C6 N1 105.1(4) . . ? C7 C6 N1 105.9(4) . . ? C8 C7 N3 123.5(5) . . ? C8 C7 C6 124.5(5) . . ? N3 C7 C6 112.0(5) . . ? C7 C8 C9 118.2(6) . . ? C10 C9 C8 119.2(6) . . ? C9 C10 C11 120.3(6) . . ? N3 C11 C10 121.6(6) . . ? C13 C12 N1 109.2(4) . . ? N4 C13 C14 121.4(5) . . ? N4 C13 C12 117.4(5) . . ? C14 C13 C12 121.1(5) . . ? C15 C14 C13 119.1(6) . . ? C14 C15 C16 119.1(6) . . ? C15 C16 C17 119.9(6) . . ? N4 C17 C16 121.8(6) . . ? N1 C18 C19 109.5(4) . . ? N5 C19 C20 121.8(5) . . ? N5 C19 C18 117.1(5) . . ? C20 C19 C18 121.0(5) . . ? C19 C20 C21 118.9(6) . . ? C22 C21 C20 119.2(6) . . ? C21 C22 C23 119.0(6) . . ? N5 C23 C22 122.8(6) . . ? Cl2 C24 Cl1 113.8(5) . . ? F2 P1 F2 180.0(3) . 3_565 ? F2 P1 F3 89.8(2) . 3_565 ? F2 P1 F3 90.2(2) 3_565 3_565 ? F2 P1 F3 90.2(2) . . ? F2 P1 F3 89.8(2) 3_565 . ? F3 P1 F3 180.0(2) 3_565 . ? F2 P1 F1 90.44(19) . . ? F2 P1 F1 89.56(19) 3_565 . ? F3 P1 F1 89.54(18) 3_565 . ? F3 P1 F1 90.46(18) . . ? F2 P1 F1 89.56(19) . 3_565 ? F2 P1 F1 90.44(19) 3_565 3_565 ? F3 P1 F1 90.46(18) 3_565 3_565 ? F3 P1 F1 89.54(18) . 3_565 ? F1 P1 F1 180.0(3) . 3_565 ? F6 P2 F5 93.1(4) . . ? F6 P2 F7 89.8(3) . . ? F5 P2 F7 177.1(4) . . ? F6 P2 F4 90.1(3) . . ? F5 P2 F4 90.9(3) . . ? F7 P2 F4 89.0(3) . . ? F6 P2 F8 178.1(4) . . ? F5 P2 F8 88.8(5) . . ? F7 P2 F8 88.3(4) . . ? F4 P2 F8 89.5(3) . . ? F6 P2 F9 89.8(3) . . ? F5 P2 F9 90.1(3) . . ? F7 P2 F9 90.0(2) . . ? F4 P2 F9 179.0(3) . . ? F8 P2 F9 90.5(3) . . ? F17 P3 F23 88.6(6) . . ? F17 P3 F19 89.5(5) . . ? F23 P3 F19 177.8(6) . . ? F17 P3 F18 92.1(5) . . ? F23 P3 F18 90.0(5) . . ? F19 P3 F18 91.1(6) . . ? F17 P3 F22 178.5(6) . . ? F23 P3 F22 92.1(6) . . ? F19 P3 F22 89.9(6) . . ? F18 P3 F22 89.3(5) . . ? F17 P3 F24 89.4(5) . . ? F23 P3 F24 87.9(5) . . ? F19 P3 F24 91.1(5) . . ? F18 P3 F24 177.4(5) . . ? F22 P3 F24 89.3(5) . . ? C25 F18 P3 31.6(14) . . ? C25 F18 Cl5 65.0(12) . . ? P3 F18 Cl5 57.2(4) . . ? N1 Ru1 N3 81.91(17) . . ? N1 Ru1 N2 82.22(17) . . ? N3 Ru1 N2 85.62(17) . . ? N1 Ru1 N5 83.33(17) . . ? N3 Ru1 N5 165.14(19) . . ? N2 Ru1 N5 90.69(17) . . ? N1 Ru1 N4 83.16(18) . . ? N3 Ru1 N4 92.25(17) . . ? N2 Ru1 N4 165.38(18) . . ? N5 Ru1 N4 87.68(17) . . ? N1 Ru1 O1 177.63(18) . . ? N3 Ru1 O1 95.77(19) . . ? N2 Ru1 O1 97.12(18) . . ? N5 Ru1 O1 98.97(18) . . ? N4 Ru1 O1 97.48(19) . . ? F18 Cl5 C25 51.9(19) . . ? F18 C25 Cl4 130(4) . . ? F18 C25 Cl5 63.2(18) . . ? Cl4 C25 Cl5 116.6(17) . . ? 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 C5 N2 C1 C2 1.1(8) . . . . ? Ru1 N2 C1 C2 176.1(4) . . . . ? N2 C1 C2 C3 0.1(9) . . . . ? C1 C2 C3 C4 -1.3(9) . . . . ? C2 C3 C4 C5 1.2(9) . . . . ? C1 N2 C5 C4 -1.2(8) . . . . ? Ru1 N2 C5 C4 -177.3(4) . . . . ? C1 N2 C5 C6 -178.3(5) . . . . ? Ru1 N2 C5 C6 5.5(5) . . . . ? C3 C4 C5 N2 0.1(8) . . . . ? C3 C4 C5 C6 176.9(5) . . . . ? N2 C5 C6 C7 70.6(6) . . . . ? C4 C5 C6 C7 -106.5(6) . . . . ? N2 C5 C6 N1 -41.8(6) . . . . ? C4 C5 C6 N1 141.2(5) . . . . ? C18 N1 C6 C5 -62.2(5) . . . . ? C12 N1 C6 C5 174.6(4) . . . . ? Ru1 N1 C6 C5 56.6(4) . . . . ? C18 N1 C6 C7 -175.3(4) . . . . ? C12 N1 C6 C7 61.6(5) . . . . ? Ru1 N1 C6 C7 -56.5(4) . . . . ? C11 N3 C7 C8 -0.3(8) . . . . ? Ru1 N3 C7 C8 177.8(4) . . . . ? C11 N3 C7 C6 178.5(5) . . . . ? Ru1 N3 C7 C6 -3.4(5) . . . . ? C5 C6 C7 C8 107.0(6) . . . . ? N1 C6 C7 C8 -141.2(5) . . . . ? C5 C6 C7 N3 -71.8(6) . . . . ? N1 C6 C7 N3 40.0(6) . . . . ? N3 C7 C8 C9 0.9(9) . . . . ? C6 C7 C8 C9 -177.7(5) . . . . ? C7 C8 C9 C10 -1.5(9) . . . . ? C8 C9 C10 C11 1.5(9) . . . . ? C7 N3 C11 C10 0.3(8) . . . . ? Ru1 N3 C11 C10 -177.4(4) . . . . ? C9 C10 C11 N3 -0.9(9) . . . . ? C18 N1 C12 C13 99.5(5) . . . . ? C6 N1 C12 C13 -137.1(4) . . . . ? Ru1 N1 C12 C13 -26.7(5) . . . . ? C17 N4 C13 C14 0.8(8) . . . . ? Ru1 N4 C13 C14 178.8(4) . . . . ? C17 N4 C13 C12 176.7(5) . . . . ? Ru1 N4 C13 C12 -5.2(6) . . . . ? N1 C12 C13 N4 20.8(6) . . . . ? N1 C12 C13 C14 -163.3(5) . . . . ? N4 C13 C14 C15 0.4(8) . . . . ? C12 C13 C14 C15 -175.4(5) . . . . ? C13 C14 C15 C16 -1.1(9) . . . . ? C14 C15 C16 C17 0.7(9) . . . . ? C13 N4 C17 C16 -1.2(8) . . . . ? Ru1 N4 C17 C16 -178.9(4) . . . . ? C15 C16 C17 N4 0.5(9) . . . . ? C12 N1 C18 C19 -101.9(5) . . . . ? C6 N1 C18 C19 134.9(5) . . . . ? Ru1 N1 C18 C19 24.0(5) . . . . ? C23 N5 C19 C20 -0.2(8) . . . . ? Ru1 N5 C19 C20 -177.9(4) . . . . ? C23 N5 C19 C18 -176.2(5) . . . . ? Ru1 N5 C19 C18 6.1(6) . . . . ? N1 C18 C19 N5 -19.6(7) . . . . ? N1 C18 C19 C20 164.5(5) . . . . ? N5 C19 C20 C21 -0.1(8) . . . . ? C18 C19 C20 C21 175.7(5) . . . . ? C19 C20 C21 C22 -0.2(9) . . . . ? C20 C21 C22 C23 0.8(9) . . . . ? C19 N5 C23 C22 0.8(8) . . . . ? Ru1 N5 C23 C22 178.1(4) . . . . ? C21 C22 C23 N5 -1.1(9) . . . . ? F17 P3 F18 C25 134(3) . . . . ? F23 P3 F18 C25 -137(3) . . . . ? F19 P3 F18 C25 45(3) . . . . ? F22 P3 F18 C25 -45(3) . . . . ? F24 P3 F18 C25 -103(13) . . . . ? F17 P3 F18 Cl5 -130.9(7) . . . . ? F23 P3 F18 Cl5 -42.3(7) . . . . ? F19 P3 F18 Cl5 139.6(8) . . . . ? F22 P3 F18 Cl5 49.8(7) . . . . ? F24 P3 F18 Cl5 -8(12) . . . . ? C18 N1 Ru1 N3 161.2(4) . . . . ? C12 N1 Ru1 N3 -73.6(3) . . . . ? C6 N1 Ru1 N3 43.5(3) . . . . ? C18 N1 Ru1 N2 74.6(3) . . . . ? C12 N1 Ru1 N2 -160.3(3) . . . . ? C6 N1 Ru1 N2 -43.2(3) . . . . ? C18 N1 Ru1 N5 -17.1(3) . . . . ? C12 N1 Ru1 N5 108.1(3) . . . . ? C6 N1 Ru1 N5 -134.8(3) . . . . ? C18 N1 Ru1 N4 -105.5(3) . . . . ? C12 N1 Ru1 N4 19.6(3) . . . . ? C6 N1 Ru1 N4 136.8(3) . . . . ? C18 N1 Ru1 O1 149(4) . . . . ? C12 N1 Ru1 O1 -86(4) . . . . ? C6 N1 Ru1 O1 31(4) . . . . ? C11 N3 Ru1 N1 152.8(5) . . . . ? C7 N3 Ru1 N1 -24.9(3) . . . . ? C11 N3 Ru1 N2 -124.4(5) . . . . ? C7 N3 Ru1 N2 57.8(4) . . . . ? C11 N3 Ru1 N5 159.5(6) . . . . ? C7 N3 Ru1 N5 -18.2(9) . . . . ? C11 N3 Ru1 N4 70.1(5) . . . . ? C7 N3 Ru1 N4 -107.7(4) . . . . ? C11 N3 Ru1 O1 -27.7(5) . . . . ? C7 N3 Ru1 O1 154.6(4) . . . . ? C1 N2 Ru1 N1 -151.9(5) . . . . ? C5 N2 Ru1 N1 23.4(3) . . . . ? C1 N2 Ru1 N3 125.7(5) . . . . ? C5 N2 Ru1 N3 -59.0(4) . . . . ? C1 N2 Ru1 N5 -68.7(5) . . . . ? C5 N2 Ru1 N5 106.6(4) . . . . ? C1 N2 Ru1 N4 -152.2(6) . . . . ? C5 N2 Ru1 N4 23.1(8) . . . . ? C1 N2 Ru1 O1 30.4(5) . . . . ? C5 N2 Ru1 O1 -154.3(3) . . . . ? C23 N5 Ru1 N1 -171.0(5) . . . . ? C19 N5 Ru1 N1 6.4(4) . . . . ? C23 N5 Ru1 N3 -177.7(6) . . . . ? C19 N5 Ru1 N3 -0.3(9) . . . . ? C23 N5 Ru1 N2 106.9(5) . . . . ? C19 N5 Ru1 N2 -75.7(4) . . . . ? C23 N5 Ru1 N4 -87.7(5) . . . . ? C19 N5 Ru1 N4 89.7(4) . . . . ? C23 N5 Ru1 O1 9.5(5) . . . . ? C19 N5 Ru1 O1 -173.0(4) . . . . ? C17 N4 Ru1 N1 169.4(5) . . . . ? C13 N4 Ru1 N1 -8.4(3) . . . . ? C17 N4 Ru1 N3 -109.1(5) . . . . ? C13 N4 Ru1 N3 73.1(4) . . . . ? C17 N4 Ru1 N2 169.7(6) . . . . ? C13 N4 Ru1 N2 -8.1(9) . . . . ? C17 N4 Ru1 N5 85.8(5) . . . . ? C13 N4 Ru1 N5 -92.0(4) . . . . ? C17 N4 Ru1 O1 -12.9(5) . . . . ? C13 N4 Ru1 O1 169.3(3) . . . . ? P3 F18 Cl5 C25 -35.2(17) . . . . ? P3 F18 C25 Cl4 -35.7(18) . . . . ? Cl5 F18 C25 Cl4 -103(3) . . . . ? P3 F18 C25 Cl5 67.5(19) . . . . ? F18 Cl5 C25 Cl4 124(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.29 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.487 _refine_diff_density_min -0.921 _refine_diff_density_rms 0.108