# Electronic Supplementary Material (ESI) for Analytical Methods # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_70herbm #TrackingRef 'Compound 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H34 Cl N3 O2 P Ru, F6 P, 2(C H4 O)' _chemical_formula_sum 'C39 H42 Cl F6 N3 O4 P2 Ru' _chemical_formula_weight 929.22 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2059(15) _cell_length_b 12.2904(18) _cell_length_c 16.590(2) _cell_angle_alpha 88.423(2) _cell_angle_beta 79.612(2) _cell_angle_gamma 67.580(2) _cell_volume 1890.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5406 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 28.29 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour red _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 0.647 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.77 _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13314 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6568 _reflns_number_gt 6322 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _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^)+(0.0478P)^2^+13.5066P] 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 6568 _refine_ls_number_parameters 514 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.002 _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 0.61481(4) 0.69920(3) 0.68081(2) 0.01243(12) Uani 1 1 d . . . P1 P 0.54333(12) 0.61965(10) 0.80096(7) 0.0148(2) Uani 1 1 d . . . Cl1 Cl 0.37641(11) 0.74408(10) 0.64992(7) 0.0168(2) Uani 1 1 d . . . N1 N 0.8114(4) 0.6836(3) 0.7076(2) 0.0157(8) Uani 1 1 d . . . N2 N 0.6561(4) 0.8225(3) 0.5865(2) 0.0162(8) Uani 1 1 d . . . N3 N 0.6890(4) 0.5402(3) 0.6107(2) 0.0154(8) Uani 1 1 d . . . O1 O 0.5514(3) 0.8592(3) 0.74891(19) 0.0168(7) Uani 1 1 d . . . O2 O 0.7351(4) 0.6466(3) 0.4312(2) 0.0222(7) Uani 1 1 d . . . C1 C 0.9408(5) 0.5962(4) 0.6812(3) 0.0207(10) Uani 1 1 d . . . H1 H 0.9453 0.5348 0.6460 0.025 Uiso 1 1 calc R . . C2 C 1.0666(5) 0.5921(5) 0.7032(3) 0.0238(11) Uani 1 1 d . . . H2 H 1.1554 0.5285 0.6840 0.029 Uiso 1 1 calc R . . C3 C 1.0615(5) 0.6819(5) 0.7536(3) 0.0254(11) Uani 1 1 d . . . H3 H 1.1465 0.6809 0.7700 0.030 Uiso 1 1 calc R . . C4 C 0.9306(5) 0.7731(4) 0.7795(3) 0.0214(10) Uani 1 1 d . . . H4 H 0.9245 0.8365 0.8135 0.026 Uiso 1 1 calc R . . C5 C 0.8078(5) 0.7714(4) 0.7556(3) 0.0173(10) Uani 1 1 d . . . C6 C 0.6655(5) 0.8698(4) 0.7849(3) 0.0207(10) Uani 1 1 d . . . H6A H 0.6404 0.8695 0.8454 0.025 Uiso 1 1 calc R . . H6B H 0.6737 0.9459 0.7707 0.025 Uiso 1 1 calc R . . C7 C 0.4882(5) 0.9545(4) 0.6972(3) 0.0191(10) Uani 1 1 d . . . H7A H 0.4739 1.0306 0.7234 0.023 Uiso 1 1 calc R . . H7B H 0.3929 0.9570 0.6899 0.023 Uiso 1 1 calc R . . C8 C 0.5857(5) 0.9361(4) 0.6157(3) 0.0176(10) Uani 1 1 d . . . C9 C 0.5969(5) 1.0316(4) 0.5729(3) 0.0213(10) Uani 1 1 d . . . H9 H 0.5447 1.1096 0.5957 0.026 Uiso 1 1 calc R . . C10 C 0.6853(6) 1.0115(5) 0.4966(3) 0.0244(11) Uani 1 1 d . . . H10 H 0.6952 1.0751 0.4658 0.029 Uiso 1 1 calc R . . C11 C 0.7590(5) 0.8960(4) 0.4662(3) 0.0211(10) Uani 1 1 d . . . H11 H 0.8201 0.8798 0.4138 0.025 Uiso 1 1 calc R . . C12 C 0.7437(5) 0.8046(4) 0.5120(3) 0.0177(10) Uani 1 1 d . . . C13 C 0.8218(5) 0.6799(4) 0.4764(3) 0.0208(10) Uani 1 1 d . . . H13A H 0.9128 0.6733 0.4397 0.025 Uiso 1 1 calc R . . H13B H 0.8467 0.6253 0.5213 0.025 Uiso 1 1 calc R . . C14 C 0.6123(5) 0.6350(4) 0.4831(3) 0.0187(10) Uani 1 1 d . . . H14A H 0.5466 0.6256 0.4491 0.022 Uiso 1 1 calc R . . H14B H 0.5586 0.7067 0.5193 0.022 Uiso 1 1 calc R . . C15 C 0.6639(5) 0.5289(4) 0.5340(3) 0.0167(9) Uani 1 1 d . . . C16 C 0.7008(5) 0.4197(4) 0.4957(3) 0.0216(10) Uani 1 1 d . . . H16 H 0.6801 0.4154 0.4426 0.026 Uiso 1 1 calc R . . C17 C 0.7669(5) 0.3171(5) 0.5337(3) 0.0248(11) Uani 1 1 d . . . H17 H 0.7893 0.2421 0.5084 0.030 Uiso 1 1 calc R . . C18 C 0.7993(5) 0.3272(4) 0.6095(3) 0.0211(10) Uani 1 1 d . . . H18 H 0.8478 0.2589 0.6371 0.025 Uiso 1 1 calc R . . C19 C 0.7602(5) 0.4379(4) 0.6447(3) 0.0172(9) Uani 1 1 d . . . H19 H 0.7850 0.4430 0.6966 0.021 Uiso 1 1 calc R . . C20 C 0.3590(5) 0.6972(4) 0.8587(3) 0.0177(10) Uani 1 1 d . . . C21 C 0.3043(5) 0.6377(5) 0.9196(3) 0.0228(10) Uani 1 1 d . . . H21 H 0.3586 0.5572 0.9272 0.027 Uiso 1 1 calc R . . C22 C 0.1713(5) 0.6950(5) 0.9691(3) 0.0259(11) Uani 1 1 d . . . H22 H 0.1354 0.6536 1.0108 0.031 Uiso 1 1 calc R . . C23 C 0.0899(5) 0.8121(5) 0.9586(3) 0.0266(11) Uani 1 1 d . . . H23 H -0.0016 0.8509 0.9925 0.032 Uiso 1 1 calc R . . C24 C 0.1430(5) 0.8720(5) 0.8982(3) 0.0264(11) Uani 1 1 d . . . H24 H 0.0875 0.9522 0.8904 0.032 Uiso 1 1 calc R . . C25 C 0.2781(5) 0.8151(4) 0.8484(3) 0.0222(10) Uani 1 1 d . . . H25 H 0.3147 0.8571 0.8074 0.027 Uiso 1 1 calc R . . C26 C 0.6504(5) 0.6192(4) 0.8790(3) 0.0180(10) Uani 1 1 d . . . C27 C 0.5910(6) 0.6962(5) 0.9472(3) 0.0283(12) Uani 1 1 d . . . H27 H 0.4903 0.7419 0.9582 0.034 Uiso 1 1 calc R . . C28 C 0.6774(6) 0.7074(5) 0.9995(3) 0.0334(13) Uani 1 1 d . . . H28 H 0.6355 0.7604 1.0462 0.040 Uiso 1 1 calc R . . C29 C 0.8247(6) 0.6412(5) 0.9840(3) 0.0271(11) Uani 1 1 d . . . H29 H 0.8841 0.6503 1.0191 0.033 Uiso 1 1 calc R . . C30 C 0.8841(6) 0.5622(4) 0.9173(3) 0.0240(11) Uani 1 1 d . . . H30 H 0.9845 0.5155 0.9071 0.029 Uiso 1 1 calc R . . C31 C 0.7988(5) 0.5507(4) 0.8653(3) 0.0193(10) Uani 1 1 d . . . H31 H 0.8408 0.4958 0.8197 0.023 Uiso 1 1 calc R . . C32 C 0.5427(5) 0.4709(4) 0.7958(3) 0.0183(10) Uani 1 1 d . . . C33 C 0.6252(5) 0.3772(4) 0.8383(3) 0.0219(10) Uani 1 1 d . . . H33 H 0.6841 0.3889 0.8727 0.026 Uiso 1 1 calc R . . C34 C 0.6198(7) 0.2666(5) 0.8297(4) 0.0331(13) Uani 1 1 d . . . H34 H 0.6779 0.2018 0.8567 0.040 Uiso 1 1 calc R . . C35 C 0.5302(7) 0.2513(5) 0.7820(4) 0.0335(13) Uani 1 1 d . . . H35 H 0.5247 0.1763 0.7775 0.040 Uiso 1 1 calc R . . C36 C 0.4475(6) 0.3447(5) 0.7402(3) 0.0251(11) Uani 1 1 d . . . H36 H 0.3853 0.3337 0.7077 0.030 Uiso 1 1 calc R . . C37 C 0.4565(5) 0.4534(4) 0.7461(3) 0.0206(10) Uani 1 1 d . . . H37 H 0.4031 0.5165 0.7160 0.025 Uiso 1 1 calc R . . P2 P 0.10800(15) 0.20176(13) 0.78333(8) 0.0276(3) Uani 1 1 d . . . F1 F 0.2107(5) 0.1107(4) 0.8376(3) 0.0658(13) Uani 1 1 d . . . F2 F 0.1106(5) 0.0916(4) 0.7330(2) 0.0559(11) Uani 1 1 d . . . F3 F 0.2460(3) 0.1991(3) 0.7197(2) 0.0335(7) Uani 1 1 d . . . F4 F 0.0087(4) 0.2901(4) 0.7280(2) 0.0528(10) Uani 1 1 d . . . F5 F -0.0292(5) 0.2006(5) 0.8451(2) 0.0741(15) Uani 1 1 d . . . F6 F 0.1088(5) 0.3081(4) 0.8335(3) 0.0706(14) Uani 1 1 d . . . O41 O 0.3930(19) 0.9971(13) -0.0614(8) 0.210(6) Uani 1 1 d DU . . H41 H 0.39(3) 1.066(6) -0.072(5) 0.315 Uiso 1 1 d D . . C41 C 0.3247(17) 0.9896(13) 0.0227(8) 0.140(5) Uani 1 1 d DU . . H41A H 0.2666 0.9419 0.0229 0.210 Uiso 1 1 calc R . . H41B H 0.2626 1.0689 0.0457 0.210 Uiso 1 1 calc R . . H41C H 0.3992 0.9530 0.0559 0.210 Uiso 1 1 calc R . . O42 O 0.8665(5) 1.0287(4) 0.7027(3) 0.0509(12) Uani 1 1 d D . . H42 H 0.906(8) 1.061(7) 0.729(5) 0.076 Uiso 1 1 d D . . C42 C 0.9662(6) 0.9601(5) 0.6309(3) 0.0402(14) Uani 1 1 d D . . H42A H 0.9766 1.0134 0.5874 0.060 Uiso 1 1 calc R . . H42B H 0.9286 0.9053 0.6115 0.060 Uiso 1 1 calc R . . H42C H 1.0604 0.9157 0.6457 0.060 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 Ru1 0.00935(19) 0.0138(2) 0.0137(2) 0.00202(13) -0.00182(13) -0.00420(14) P1 0.0122(6) 0.0166(6) 0.0153(6) 0.0030(4) -0.0022(4) -0.0054(5) Cl1 0.0118(5) 0.0195(5) 0.0189(5) 0.0028(4) -0.0038(4) -0.0054(4) N1 0.0116(19) 0.0152(19) 0.0174(19) 0.0027(15) -0.0004(15) -0.0031(15) N2 0.0119(19) 0.020(2) 0.019(2) 0.0036(16) -0.0053(15) -0.0072(16) N3 0.0104(18) 0.0171(19) 0.019(2) 0.0023(15) 0.0002(15) -0.0068(15) O1 0.0140(16) 0.0164(16) 0.0207(17) 0.0020(13) -0.0036(13) -0.0063(13) O2 0.0249(19) 0.0287(19) 0.0167(17) 0.0012(14) -0.0004(14) -0.0157(15) C1 0.021(3) 0.022(2) 0.019(2) 0.0032(19) -0.003(2) -0.008(2) C2 0.015(2) 0.028(3) 0.023(3) 0.003(2) -0.002(2) -0.004(2) C3 0.017(3) 0.035(3) 0.029(3) 0.006(2) -0.008(2) -0.014(2) C4 0.022(3) 0.025(3) 0.021(2) 0.002(2) -0.006(2) -0.013(2) C5 0.018(2) 0.018(2) 0.016(2) 0.0063(18) -0.0030(18) -0.0063(19) C6 0.019(2) 0.023(3) 0.021(2) -0.0004(19) -0.007(2) -0.009(2) C7 0.017(2) 0.016(2) 0.022(2) 0.0041(19) -0.0044(19) -0.0030(19) C8 0.014(2) 0.019(2) 0.023(2) 0.0033(19) -0.0062(19) -0.0087(19) C9 0.022(3) 0.020(2) 0.026(3) 0.006(2) -0.011(2) -0.010(2) C10 0.026(3) 0.027(3) 0.028(3) 0.011(2) -0.011(2) -0.016(2) C11 0.020(2) 0.029(3) 0.018(2) 0.007(2) -0.0048(19) -0.013(2) C12 0.013(2) 0.025(2) 0.018(2) 0.0007(19) -0.0045(18) -0.0096(19) C13 0.017(2) 0.025(3) 0.020(2) -0.0007(19) 0.0024(19) -0.010(2) C14 0.017(2) 0.025(2) 0.018(2) 0.0023(19) -0.0037(19) -0.012(2) C15 0.011(2) 0.024(2) 0.017(2) 0.0001(19) -0.0006(18) -0.0096(19) C16 0.017(2) 0.028(3) 0.021(2) -0.003(2) -0.0013(19) -0.011(2) C17 0.018(3) 0.023(3) 0.032(3) -0.006(2) 0.003(2) -0.010(2) C18 0.014(2) 0.019(2) 0.028(3) 0.002(2) 0.0002(19) -0.0045(19) C19 0.012(2) 0.022(2) 0.018(2) 0.0043(19) -0.0017(18) -0.0076(19) C20 0.013(2) 0.024(2) 0.016(2) 0.0007(19) -0.0030(18) -0.0068(19) C21 0.021(3) 0.028(3) 0.020(2) 0.004(2) -0.004(2) -0.010(2) C22 0.021(3) 0.038(3) 0.020(2) 0.007(2) 0.000(2) -0.015(2) C23 0.016(2) 0.037(3) 0.022(3) -0.001(2) 0.000(2) -0.007(2) C24 0.016(3) 0.028(3) 0.029(3) 0.003(2) -0.003(2) -0.002(2) C25 0.019(2) 0.026(3) 0.020(2) 0.002(2) 0.0001(19) -0.009(2) C26 0.018(2) 0.021(2) 0.017(2) 0.0059(18) -0.0053(19) -0.009(2) C27 0.020(3) 0.034(3) 0.027(3) -0.002(2) -0.005(2) -0.007(2) C28 0.031(3) 0.044(3) 0.022(3) -0.006(2) -0.009(2) -0.007(3) C29 0.026(3) 0.036(3) 0.027(3) 0.009(2) -0.015(2) -0.016(2) C30 0.020(3) 0.026(3) 0.027(3) 0.011(2) -0.010(2) -0.008(2) C31 0.019(2) 0.020(2) 0.020(2) 0.0053(19) -0.0045(19) -0.008(2) C32 0.016(2) 0.019(2) 0.020(2) 0.0019(19) 0.0012(19) -0.0091(19) C33 0.022(3) 0.026(3) 0.026(3) 0.008(2) -0.012(2) -0.015(2) C34 0.040(3) 0.024(3) 0.042(3) 0.014(2) -0.014(3) -0.017(3) C35 0.041(3) 0.027(3) 0.041(3) 0.006(2) -0.011(3) -0.021(3) C36 0.030(3) 0.029(3) 0.021(3) 0.001(2) -0.004(2) -0.016(2) C37 0.018(2) 0.024(3) 0.019(2) 0.0023(19) -0.0009(19) -0.008(2) P2 0.0236(7) 0.0302(7) 0.0198(7) -0.0017(5) -0.0026(5) -0.0006(6) F1 0.064(3) 0.058(3) 0.047(2) 0.024(2) -0.013(2) 0.007(2) F2 0.069(3) 0.061(3) 0.049(2) -0.0130(19) 0.017(2) -0.050(2) F3 0.0244(16) 0.0276(16) 0.048(2) 0.0069(14) -0.0051(14) -0.0108(13) F4 0.033(2) 0.069(3) 0.041(2) 0.0129(19) -0.0183(17) 0.0011(18) F5 0.041(2) 0.111(4) 0.038(2) 0.007(2) 0.0198(19) -0.006(2) F6 0.085(3) 0.052(3) 0.059(3) -0.028(2) -0.030(2) 0.000(2) O41 0.209(9) 0.209(9) 0.207(9) -0.001(8) -0.042(8) -0.073(8) C41 0.143(9) 0.133(8) 0.143(9) -0.027(7) 0.011(7) -0.065(7) O42 0.045(3) 0.039(3) 0.064(3) -0.001(2) 0.001(2) -0.016(2) C42 0.033(3) 0.050(4) 0.040(3) 0.011(3) -0.008(3) -0.019(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 N1 2.070(4) . ? Ru1 N3 2.103(4) . ? Ru1 O1 2.109(3) . ? Ru1 N2 2.245(4) . ? Ru1 P1 2.3181(12) . ? Ru1 Cl1 2.4284(12) . ? P1 C32 1.835(5) . ? P1 C26 1.837(5) . ? P1 C20 1.843(5) . ? N1 C5 1.343(6) . ? N1 C1 1.351(6) . ? N2 C12 1.356(6) . ? N2 C8 1.359(6) . ? N3 C19 1.356(6) . ? N3 C15 1.363(6) . ? O1 C7 1.448(5) . ? O1 C6 1.449(6) . ? O2 C13 1.430(6) . ? O2 C14 1.440(6) . ? C1 C2 1.379(7) . ? C2 C3 1.383(7) . ? C3 C4 1.380(7) . ? C4 C5 1.389(7) . ? C5 C6 1.499(7) . ? C7 C8 1.493(7) . ? C8 C9 1.386(7) . ? C9 C10 1.384(7) . ? C10 C11 1.386(7) . ? C11 C12 1.382(7) . ? C12 C13 1.511(7) . ? C14 C15 1.505(6) . ? C15 C16 1.387(7) . ? C16 C17 1.379(7) . ? C17 C18 1.377(7) . ? C18 C19 1.378(7) . ? C20 C25 1.391(7) . ? C20 C21 1.391(7) . ? C21 C22 1.383(7) . ? C22 C23 1.385(8) . ? C23 C24 1.381(7) . ? C24 C25 1.400(7) . ? C26 C27 1.385(7) . ? C26 C31 1.403(7) . ? C27 C28 1.387(8) . ? C28 C29 1.388(8) . ? C29 C30 1.381(8) . ? C30 C31 1.376(7) . ? C32 C37 1.384(7) . ? C32 C33 1.401(7) . ? C33 C34 1.393(7) . ? C34 C35 1.379(8) . ? C35 C36 1.392(8) . ? C36 C37 1.381(7) . ? P2 F6 1.572(4) . ? P2 F4 1.577(4) . ? P2 F5 1.584(4) . ? P2 F3 1.590(3) . ? P2 F1 1.597(4) . ? P2 F2 1.599(4) . ? O41 C41 1.4602(11) . ? O42 C42 1.4593(10) . ? 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 Ru1 N3 97.28(15) . . ? N1 Ru1 O1 80.04(13) . . ? N3 Ru1 O1 176.88(13) . . ? N1 Ru1 N2 84.05(14) . . ? N3 Ru1 N2 101.78(14) . . ? O1 Ru1 N2 76.44(13) . . ? N1 Ru1 P1 95.31(11) . . ? N3 Ru1 P1 94.11(10) . . ? O1 Ru1 P1 87.75(9) . . ? N2 Ru1 P1 164.06(11) . . ? N1 Ru1 Cl1 172.79(11) . . ? N3 Ru1 Cl1 88.90(11) . . ? O1 Ru1 Cl1 93.67(9) . . ? N2 Ru1 Cl1 91.08(10) . . ? P1 Ru1 Cl1 87.91(4) . . ? C32 P1 C26 106.4(2) . . ? C32 P1 C20 99.0(2) . . ? C26 P1 C20 100.8(2) . . ? C32 P1 Ru1 118.70(15) . . ? C26 P1 Ru1 111.63(15) . . ? C20 P1 Ru1 118.05(16) . . ? C5 N1 C1 117.6(4) . . ? C5 N1 Ru1 115.5(3) . . ? C1 N1 Ru1 126.9(3) . . ? C12 N2 C8 116.5(4) . . ? C12 N2 Ru1 132.8(3) . . ? C8 N2 Ru1 110.4(3) . . ? C19 N3 C15 115.5(4) . . ? C19 N3 Ru1 119.0(3) . . ? C15 N3 Ru1 125.4(3) . . ? C7 O1 C6 114.1(3) . . ? C7 O1 Ru1 107.9(3) . . ? C6 O1 Ru1 113.6(3) . . ? C13 O2 C14 112.6(3) . . ? N1 C1 C2 123.0(5) . . ? C1 C2 C3 119.0(5) . . ? C4 C3 C2 118.7(5) . . ? C3 C4 C5 119.4(5) . . ? N1 C5 C4 122.3(4) . . ? N1 C5 C6 118.5(4) . . ? C4 C5 C6 119.2(4) . . ? O1 C6 C5 111.9(4) . . ? O1 C7 C8 109.4(4) . . ? N2 C8 C9 123.6(4) . . ? N2 C8 C7 115.9(4) . . ? C9 C8 C7 120.4(4) . . ? C10 C9 C8 118.9(5) . . ? C9 C10 C11 118.2(4) . . ? C12 C11 C10 120.1(5) . . ? N2 C12 C11 122.7(4) . . ? N2 C12 C13 118.3(4) . . ? C11 C12 C13 118.9(4) . . ? O2 C13 C12 111.2(4) . . ? O2 C14 C15 108.9(4) . . ? N3 C15 C16 122.0(4) . . ? N3 C15 C14 120.7(4) . . ? C16 C15 C14 116.9(4) . . ? C17 C16 C15 121.0(5) . . ? C18 C17 C16 117.6(5) . . ? C17 C18 C19 118.9(5) . . ? N3 C19 C18 124.8(4) . . ? C25 C20 C21 119.0(4) . . ? C25 C20 P1 122.6(4) . . ? C21 C20 P1 118.2(4) . . ? C22 C21 C20 120.4(5) . . ? C21 C22 C23 120.7(5) . . ? C24 C23 C22 119.4(5) . . ? C23 C24 C25 120.4(5) . . ? C20 C25 C24 120.1(5) . . ? C27 C26 C31 118.5(5) . . ? C27 C26 P1 121.0(4) . . ? C31 C26 P1 120.1(4) . . ? C26 C27 C28 120.6(5) . . ? C27 C28 C29 120.2(5) . . ? C30 C29 C28 119.5(5) . . ? C31 C30 C29 120.4(5) . . ? C30 C31 C26 120.7(5) . . ? C37 C32 C33 120.1(4) . . ? C37 C32 P1 116.7(4) . . ? C33 C32 P1 123.2(4) . . ? C34 C33 C32 119.3(5) . . ? C35 C34 C33 120.0(5) . . ? C34 C35 C36 120.6(5) . . ? C37 C36 C35 119.6(5) . . ? C36 C37 C32 120.4(5) . . ? F6 P2 F4 90.4(2) . . ? F6 P2 F5 91.1(3) . . ? F4 P2 F5 90.8(2) . . ? F6 P2 F3 90.9(2) . . ? F4 P2 F3 89.3(2) . . ? F5 P2 F3 178.1(3) . . ? F6 P2 F1 90.4(3) . . ? F4 P2 F1 178.8(2) . . ? F5 P2 F1 90.0(2) . . ? F3 P2 F1 89.8(2) . . ? F6 P2 F2 178.6(3) . . ? F4 P2 F2 90.9(2) . . ? F5 P2 F2 89.4(3) . . ? F3 P2 F2 88.65(19) . . ? F1 P2 F2 88.3(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 N1 Ru1 P1 C32 -107.3(2) . . . . ? N3 Ru1 P1 C32 -9.5(2) . . . . ? O1 Ru1 P1 C32 173.0(2) . . . . ? N2 Ru1 P1 C32 165.8(4) . . . . ? Cl1 Ru1 P1 C32 79.21(18) . . . . ? N1 Ru1 P1 C26 17.1(2) . . . . ? N3 Ru1 P1 C26 114.8(2) . . . . ? O1 Ru1 P1 C26 -62.69(19) . . . . ? N2 Ru1 P1 C26 -69.8(4) . . . . ? Cl1 Ru1 P1 C26 -156.45(17) . . . . ? N1 Ru1 P1 C20 133.2(2) . . . . ? N3 Ru1 P1 C20 -129.1(2) . . . . ? O1 Ru1 P1 C20 53.44(19) . . . . ? N2 Ru1 P1 C20 46.3(4) . . . . ? Cl1 Ru1 P1 C20 -40.31(18) . . . . ? N3 Ru1 N1 C5 -178.4(3) . . . . ? O1 Ru1 N1 C5 3.2(3) . . . . ? N2 Ru1 N1 C5 80.4(3) . . . . ? P1 Ru1 N1 C5 -83.6(3) . . . . ? N3 Ru1 N1 C1 2.5(4) . . . . ? O1 Ru1 N1 C1 -175.8(4) . . . . ? N2 Ru1 N1 C1 -98.6(4) . . . . ? P1 Ru1 N1 C1 97.4(4) . . . . ? N1 Ru1 N2 C12 76.3(4) . . . . ? N3 Ru1 N2 C12 -19.9(4) . . . . ? O1 Ru1 N2 C12 157.5(4) . . . . ? P1 Ru1 N2 C12 164.8(3) . . . . ? Cl1 Ru1 N2 C12 -109.0(4) . . . . ? N1 Ru1 N2 C8 -97.5(3) . . . . ? N3 Ru1 N2 C8 166.3(3) . . . . ? O1 Ru1 N2 C8 -16.3(3) . . . . ? P1 Ru1 N2 C8 -9.0(6) . . . . ? Cl1 Ru1 N2 C8 77.2(3) . . . . ? N1 Ru1 N3 C19 56.3(3) . . . . ? N2 Ru1 N3 C19 141.7(3) . . . . ? P1 Ru1 N3 C19 -39.6(3) . . . . ? Cl1 Ru1 N3 C19 -127.4(3) . . . . ? N1 Ru1 N3 C15 -128.1(3) . . . . ? N2 Ru1 N3 C15 -42.7(4) . . . . ? P1 Ru1 N3 C15 136.0(3) . . . . ? Cl1 Ru1 N3 C15 48.1(3) . . . . ? N1 Ru1 O1 C7 121.3(3) . . . . ? N2 Ru1 O1 C7 35.1(3) . . . . ? P1 Ru1 O1 C7 -142.9(3) . . . . ? Cl1 Ru1 O1 C7 -55.1(3) . . . . ? N1 Ru1 O1 C6 -6.2(3) . . . . ? N2 Ru1 O1 C6 -92.4(3) . . . . ? P1 Ru1 O1 C6 89.6(3) . . . . ? Cl1 Ru1 O1 C6 177.4(3) . . . . ? C5 N1 C1 C2 1.9(7) . . . . ? Ru1 N1 C1 C2 -179.1(3) . . . . ? N1 C1 C2 C3 -0.9(7) . . . . ? C1 C2 C3 C4 -0.5(7) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C1 N1 C5 C4 -1.4(6) . . . . ? Ru1 N1 C5 C4 179.4(3) . . . . ? C1 N1 C5 C6 179.5(4) . . . . ? Ru1 N1 C5 C6 0.3(5) . . . . ? C3 C4 C5 N1 0.0(7) . . . . ? C3 C4 C5 C6 179.1(4) . . . . ? C7 O1 C6 C5 -116.3(4) . . . . ? Ru1 O1 C6 C5 7.9(5) . . . . ? N1 C5 C6 O1 -5.6(6) . . . . ? C4 C5 C6 O1 175.3(4) . . . . ? C6 O1 C7 C8 78.3(5) . . . . ? Ru1 O1 C7 C8 -49.0(4) . . . . ? C12 N2 C8 C9 1.5(7) . . . . ? Ru1 N2 C8 C9 176.5(4) . . . . ? C12 N2 C8 C7 179.2(4) . . . . ? Ru1 N2 C8 C7 -5.8(5) . . . . ? O1 C7 C8 N2 36.4(5) . . . . ? O1 C7 C8 C9 -145.8(4) . . . . ? N2 C8 C9 C10 -0.7(7) . . . . ? C7 C8 C9 C10 -178.3(4) . . . . ? C8 C9 C10 C11 0.0(7) . . . . ? C9 C10 C11 C12 -0.3(7) . . . . ? C8 N2 C12 C11 -1.8(6) . . . . ? Ru1 N2 C12 C11 -175.3(3) . . . . ? C8 N2 C12 C13 -178.8(4) . . . . ? Ru1 N2 C12 C13 7.7(6) . . . . ? C10 C11 C12 N2 1.2(7) . . . . ? C10 C11 C12 C13 178.2(4) . . . . ? C14 O2 C13 C12 -68.7(5) . . . . ? N2 C12 C13 O2 87.1(5) . . . . ? C11 C12 C13 O2 -90.0(5) . . . . ? C13 O2 C14 C15 -69.2(5) . . . . ? C19 N3 C15 C16 4.0(6) . . . . ? Ru1 N3 C15 C16 -171.7(3) . . . . ? C19 N3 C15 C14 -168.1(4) . . . . ? Ru1 N3 C15 C14 16.2(6) . . . . ? O2 C14 C15 N3 93.6(5) . . . . ? O2 C14 C15 C16 -78.9(5) . . . . ? N3 C15 C16 C17 -1.0(7) . . . . ? C14 C15 C16 C17 171.4(4) . . . . ? C15 C16 C17 C18 -2.1(7) . . . . ? C16 C17 C18 C19 2.1(7) . . . . ? C15 N3 C19 C18 -4.1(6) . . . . ? Ru1 N3 C19 C18 171.9(4) . . . . ? C17 C18 C19 N3 1.0(7) . . . . ? C32 P1 C20 C25 -149.2(4) . . . . ? C26 P1 C20 C25 102.0(4) . . . . ? Ru1 P1 C20 C25 -19.8(5) . . . . ? C32 P1 C20 C21 36.3(4) . . . . ? C26 P1 C20 C21 -72.5(4) . . . . ? Ru1 P1 C20 C21 165.7(3) . . . . ? C25 C20 C21 C22 0.0(7) . . . . ? P1 C20 C21 C22 174.7(4) . . . . ? C20 C21 C22 C23 0.5(8) . . . . ? C21 C22 C23 C24 -0.4(8) . . . . ? C22 C23 C24 C25 -0.3(8) . . . . ? C21 C20 C25 C24 -0.7(7) . . . . ? P1 C20 C25 C24 -175.2(4) . . . . ? C23 C24 C25 C20 0.9(8) . . . . ? C32 P1 C26 C27 -121.3(4) . . . . ? C20 P1 C26 C27 -18.5(5) . . . . ? Ru1 P1 C26 C27 107.7(4) . . . . ? C32 P1 C26 C31 66.6(4) . . . . ? C20 P1 C26 C31 169.4(4) . . . . ? Ru1 P1 C26 C31 -64.4(4) . . . . ? C31 C26 C27 C28 1.6(8) . . . . ? P1 C26 C27 C28 -170.7(4) . . . . ? C26 C27 C28 C29 0.1(9) . . . . ? C27 C28 C29 C30 -1.6(9) . . . . ? C28 C29 C30 C31 1.4(8) . . . . ? C29 C30 C31 C26 0.2(7) . . . . ? C27 C26 C31 C30 -1.8(7) . . . . ? P1 C26 C31 C30 170.6(4) . . . . ? C26 P1 C32 C37 174.0(4) . . . . ? C20 P1 C32 C37 69.9(4) . . . . ? Ru1 P1 C32 C37 -59.1(4) . . . . ? C26 P1 C32 C33 -6.6(5) . . . . ? C20 P1 C32 C33 -110.8(4) . . . . ? Ru1 P1 C32 C33 120.2(4) . . . . ? C37 C32 C33 C34 0.4(7) . . . . ? P1 C32 C33 C34 -178.9(4) . . . . ? C32 C33 C34 C35 -2.3(8) . . . . ? C33 C34 C35 C36 1.9(9) . . . . ? C34 C35 C36 C37 0.5(8) . . . . ? C35 C36 C37 C32 -2.5(8) . . . . ? C33 C32 C37 C36 2.0(7) . . . . ? P1 C32 C37 C36 -178.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.271 _refine_diff_density_min -0.877 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 919778'