# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_s3985a #TrackingRef 'web_deposit_cif_file_0_A.L.Spek_1336402263.s3985a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H31 Cl N4 O2 Ru' _chemical_formula_sum 'C31 H31 Cl N4 O2 Ru' _chemical_formula_weight 628.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P 21/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 8.0751(3) _cell_length_b 25.4734(8) _cell_length_c 14.7742(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.606(3) _cell_angle_gamma 90.00 _cell_volume 2825.53(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13215 _cell_measurement_theta_min 1.61 _cell_measurement_theta_max 27.50 _exptl_crystal_description rod _exptl_crystal_colour 'dark purple' _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.762 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _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 30372 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.36 _reflns_number_total 6399 _reflns_number_gt 5366 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'PEAKREF (Schreurs, 2005)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'DIRDIF99 (Beurskens et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0197P)^2^+2.2272P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6399 _refine_ls_number_parameters 360 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0539 _refine_ls_wR_factor_gt 0.0498 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1137(2) 0.06669(7) 0.43796(13) 0.0155(3) Uani 1 1 d . . . C2 C -0.2010(2) 0.05440(7) 0.50104(13) 0.0188(4) Uani 1 1 d . . . H2 H -0.2501 0.0205 0.5004 0.023 Uiso 1 1 calc R . . C3 C -0.2148(2) 0.09290(8) 0.56499(13) 0.0207(4) Uani 1 1 d . . . H3 H -0.2736 0.0851 0.6085 0.025 Uiso 1 1 calc R . . C4 C -0.1430(2) 0.14257(7) 0.56541(13) 0.0187(4) Uani 1 1 d . . . H4 H -0.1520 0.1688 0.6092 0.022 Uiso 1 1 calc R . . C5 C -0.0579(2) 0.15348(7) 0.50093(12) 0.0158(3) Uani 1 1 d . . . C6 C -0.0822(2) 0.03361(7) 0.36625(13) 0.0163(4) Uani 1 1 d . . . H6 H -0.1289 -0.0010 0.3542 0.020 Uiso 1 1 calc R . . C7 C 0.0166(2) 0.02067(7) 0.23801(13) 0.0176(4) Uani 1 1 d . . . C8 C -0.1440(3) 0.01169(8) 0.15892(14) 0.0241(4) Uani 1 1 d . . . C9 C -0.1417(3) -0.02237(8) 0.08561(15) 0.0313(5) Uani 1 1 d . . . H9 H -0.2493 -0.0286 0.0319 0.038 Uiso 1 1 calc R . . C10 C 0.0136(3) -0.04758(8) 0.08846(16) 0.0306(5) Uani 1 1 d . . . C11 C 0.1702(3) -0.03573(8) 0.16481(15) 0.0275(4) Uani 1 1 d . . . H11 H 0.2777 -0.0515 0.1662 0.033 Uiso 1 1 calc R . . C12 C 0.1769(3) -0.00145(7) 0.24012(14) 0.0202(4) Uani 1 1 d . . . C13 C -0.3154(3) 0.04005(9) 0.14875(16) 0.0339(5) Uani 1 1 d . . . H13A H -0.3980 0.0385 0.0808 0.051 Uiso 1 1 calc R . . H13B H -0.2890 0.0768 0.1683 0.051 Uiso 1 1 calc R . . H13C H -0.3700 0.0232 0.1905 0.051 Uiso 1 1 calc R . . C14 C 0.0088(4) -0.08680(9) 0.01051(18) 0.0449(6) Uani 1 1 d . . . H14A H -0.0710 -0.0740 -0.0531 0.067 Uiso 0.79(3) 1 calc PR . . H14B H -0.0346 -0.1206 0.0243 0.067 Uiso 0.79(3) 1 calc PR . . H14C H 0.1290 -0.0912 0.0100 0.067 Uiso 0.79(3) 1 calc PR . . H14D H 0.0866 -0.1165 0.0405 0.067 Uiso 0.21(3) 1 calc PR . . H14E H 0.0502 -0.0699 -0.0369 0.067 Uiso 0.21(3) 1 calc PR . . H14F H -0.1134 -0.0994 -0.0226 0.067 Uiso 0.21(3) 1 calc PR . . C15 C 0.3556(2) 0.00972(8) 0.31888(15) 0.0236(4) Uani 1 1 d . . . H15A H 0.4206 0.0352 0.2949 0.035 Uiso 1 1 calc R . . H15B H 0.4244 -0.0229 0.3367 0.035 Uiso 1 1 calc R . . H15C H 0.3378 0.0241 0.3762 0.035 Uiso 1 1 calc R . . C16 C 0.0253(2) 0.20210(7) 0.48957(13) 0.0169(4) Uani 1 1 d . . . H16 H 0.0187 0.2330 0.5240 0.020 Uiso 1 1 calc R . . C17 C 0.1755(2) 0.25000(7) 0.40518(13) 0.0168(4) Uani 1 1 d . . . C18 C 0.0544(2) 0.28639(7) 0.34484(13) 0.0206(4) Uani 1 1 d . . . C19 C 0.1246(3) 0.33107(8) 0.31642(15) 0.0274(4) Uani 1 1 d . . . H19 H 0.0450 0.3563 0.2756 0.033 Uiso 1 1 calc R . . C20 C 0.3068(3) 0.33966(8) 0.34601(17) 0.0326(5) Uani 1 1 d . . . C21 C 0.4224(3) 0.30414(8) 0.40980(17) 0.0296(5) Uani 1 1 d . . . H21 H 0.5469 0.3107 0.4329 0.036 Uiso 1 1 calc R . . C22 C 0.3603(2) 0.25907(7) 0.44085(14) 0.0219(4) Uani 1 1 d . . . C23 C -0.1454(3) 0.27892(8) 0.31053(16) 0.0283(4) Uani 1 1 d . . . H23A H -0.2054 0.3079 0.2673 0.043 Uiso 1 1 calc R . . H23B H -0.1818 0.2784 0.3669 0.043 Uiso 1 1 calc R . . H23C H -0.1782 0.2456 0.2752 0.043 Uiso 1 1 calc R . . C24 C 0.3783(4) 0.38698(10) 0.3093(2) 0.0541(7) Uani 1 1 d . . . H24A H 0.4584 0.4070 0.3648 0.081 Uiso 0.66(3) 1 calc PR . . H24B H 0.2788 0.4094 0.2705 0.081 Uiso 0.66(3) 1 calc PR . . H24C H 0.4437 0.3751 0.2688 0.081 Uiso 0.66(3) 1 calc PR . . H24D H 0.3288 0.3873 0.2379 0.081 Uiso 0.34(3) 1 calc PR . . H24E H 0.5084 0.3849 0.3323 0.081 Uiso 0.34(3) 1 calc PR . . H24F H 0.3436 0.4192 0.3339 0.081 Uiso 0.34(3) 1 calc PR . . C25 C 0.4885(3) 0.22313(8) 0.51471(17) 0.0304(5) Uani 1 1 d . . . H25A H 0.6092 0.2375 0.5348 0.046 Uiso 1 1 calc R . . H25B H 0.4854 0.1883 0.4858 0.046 Uiso 1 1 calc R . . H25C H 0.4542 0.2201 0.5716 0.046 Uiso 1 1 calc R . . C26 C 0.4530(2) 0.13880(7) 0.32152(13) 0.0164(4) Uani 1 1 d . . . H26 H 0.5126 0.1236 0.3838 0.020 Uiso 1 1 calc R . . C27 C 0.5515(2) 0.15279(7) 0.26569(14) 0.0198(4) Uani 1 1 d . . . H27 H 0.6767 0.1474 0.2900 0.024 Uiso 1 1 calc R . . C28 C 0.4669(2) 0.17453(7) 0.17467(14) 0.0220(4) Uani 1 1 d . . . H28 H 0.5323 0.1836 0.1350 0.026 Uiso 1 1 calc R . . C29 C 0.2838(2) 0.18287(7) 0.14222(14) 0.0205(4) Uani 1 1 d . . . H29 H 0.2222 0.1979 0.0800 0.025 Uiso 1 1 calc R . . C30 C 0.1925(2) 0.16888(7) 0.20189(12) 0.0146(3) Uani 1 1 d . . . C31 C -0.0064(2) 0.17718(7) 0.17294(13) 0.0156(3) Uani 1 1 d . . . N1 N -0.04664(18) 0.11586(6) 0.43778(10) 0.0139(3) Uani 1 1 d . . . N2 N 0.01242(18) 0.05266(6) 0.31855(11) 0.0147(3) Uani 1 1 d . . . N3 N 0.11009(18) 0.20113(6) 0.42926(10) 0.0148(3) Uani 1 1 d . . . N4 N 0.27489(18) 0.14612(6) 0.29016(10) 0.0132(3) Uani 1 1 d . . . O1 O -0.07197(15) 0.15893(5) 0.23440(9) 0.0157(3) Uani 1 1 d . . . O2 O -0.09251(16) 0.19975(5) 0.09649(10) 0.0235(3) Uani 1 1 d . . . Cl1 Cl 0.33014(6) 0.093662(18) 0.50749(3) 0.01969(9) Uani 1 1 d . . . Ru1 Ru 0.105697(17) 0.128814(5) 0.365045(10) 0.01176(4) 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 0.0116(8) 0.0160(9) 0.0180(9) 0.0025(7) 0.0043(7) 0.0003(7) C2 0.0137(8) 0.0213(10) 0.0212(9) 0.0069(7) 0.0063(7) 0.0001(7) C3 0.0162(9) 0.0304(10) 0.0182(9) 0.0080(8) 0.0093(7) 0.0045(7) C4 0.0160(8) 0.0260(10) 0.0153(8) 0.0011(7) 0.0070(7) 0.0039(7) C5 0.0136(8) 0.0184(9) 0.0147(8) 0.0001(7) 0.0043(7) 0.0021(7) C6 0.0150(8) 0.0137(8) 0.0189(9) 0.0017(7) 0.0048(7) -0.0002(7) C7 0.0227(9) 0.0127(8) 0.0196(9) -0.0011(7) 0.0104(7) -0.0015(7) C8 0.0246(10) 0.0230(10) 0.0240(10) -0.0037(8) 0.0080(8) -0.0028(8) C9 0.0357(12) 0.0310(12) 0.0243(11) -0.0097(9) 0.0079(9) -0.0084(9) C10 0.0491(13) 0.0201(10) 0.0292(11) -0.0056(9) 0.0223(10) -0.0031(9) C11 0.0377(12) 0.0199(10) 0.0334(11) 0.0004(9) 0.0230(10) 0.0058(9) C12 0.0261(10) 0.0152(9) 0.0236(10) 0.0030(7) 0.0141(8) 0.0012(7) C13 0.0214(10) 0.0435(13) 0.0289(11) -0.0105(10) 0.0000(9) 0.0023(9) C14 0.0733(18) 0.0304(13) 0.0396(14) -0.0143(11) 0.0307(13) -0.0046(12) C15 0.0213(9) 0.0219(10) 0.0316(11) 0.0040(8) 0.0144(8) 0.0043(8) C16 0.0170(8) 0.0166(9) 0.0177(9) -0.0031(7) 0.0068(7) 0.0003(7) C17 0.0197(9) 0.0149(9) 0.0183(9) -0.0041(7) 0.0100(7) -0.0035(7) C18 0.0241(9) 0.0180(9) 0.0202(9) -0.0032(7) 0.0088(8) -0.0021(7) C19 0.0375(12) 0.0189(10) 0.0260(10) 0.0015(8) 0.0118(9) -0.0017(9) C20 0.0431(13) 0.0225(11) 0.0404(13) -0.0041(9) 0.0251(11) -0.0118(9) C21 0.0255(10) 0.0256(11) 0.0447(13) -0.0082(9) 0.0210(10) -0.0094(8) C22 0.0209(9) 0.0190(9) 0.0281(10) -0.0073(8) 0.0116(8) -0.0024(7) C23 0.0229(10) 0.0231(10) 0.0342(12) 0.0037(9) 0.0048(9) 0.0029(8) C24 0.0667(18) 0.0348(14) 0.074(2) 0.0092(13) 0.0414(16) -0.0149(13) C25 0.0172(9) 0.0243(11) 0.0435(13) -0.0084(9) 0.0040(9) -0.0011(8) C26 0.0132(8) 0.0176(9) 0.0174(9) 0.0025(7) 0.0045(7) 0.0012(7) C27 0.0124(8) 0.0221(10) 0.0258(10) 0.0027(8) 0.0083(7) 0.0013(7) C28 0.0193(9) 0.0256(10) 0.0262(10) 0.0057(8) 0.0143(8) 0.0009(8) C29 0.0193(9) 0.0240(10) 0.0198(9) 0.0070(8) 0.0088(8) 0.0029(7) C30 0.0130(8) 0.0139(8) 0.0166(8) 0.0013(7) 0.0051(7) 0.0010(6) C31 0.0140(8) 0.0155(9) 0.0172(9) -0.0005(7) 0.0056(7) 0.0004(7) N1 0.0108(6) 0.0159(7) 0.0148(7) 0.0015(6) 0.0046(6) 0.0007(5) N2 0.0130(7) 0.0133(7) 0.0170(7) 0.0004(6) 0.0047(6) 0.0012(6) N3 0.0127(7) 0.0153(7) 0.0152(7) -0.0004(6) 0.0039(6) -0.0001(6) N4 0.0123(7) 0.0122(7) 0.0152(7) -0.0005(6) 0.0054(6) -0.0005(5) O1 0.0116(6) 0.0190(6) 0.0171(6) 0.0028(5) 0.0058(5) 0.0015(5) O2 0.0161(6) 0.0312(8) 0.0223(7) 0.0107(6) 0.0060(5) 0.0056(5) Cl1 0.0163(2) 0.0224(2) 0.0182(2) 0.00344(17) 0.00379(17) 0.00186(17) Ru1 0.01043(6) 0.01251(7) 0.01326(7) 0.00041(6) 0.00542(5) 0.00004(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.365(2) . ? C1 C2 1.395(2) . ? C1 C6 1.448(2) . ? C2 C3 1.394(3) . ? C2 H2 0.9500 . ? C3 C4 1.391(3) . ? C3 H3 0.9500 . ? C4 C5 1.393(2) . ? C4 H4 0.9500 . ? C5 N1 1.364(2) . ? C5 C16 1.448(2) . ? C6 N2 1.308(2) . ? C6 H6 0.9500 . ? C7 C12 1.402(2) . ? C7 C8 1.408(3) . ? C7 N2 1.453(2) . ? C8 C9 1.393(3) . ? C8 C13 1.519(3) . ? C9 C10 1.395(3) . ? C9 H9 0.9500 . ? C10 C11 1.383(3) . ? C10 C14 1.514(3) . ? C11 C12 1.400(3) . ? C11 H11 0.9500 . ? C12 C15 1.510(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C14 H14D 0.9800 . ? C14 H14E 0.9800 . ? C14 H14F 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N3 1.309(2) . ? C16 H16 0.9500 . ? C17 C18 1.403(3) . ? C17 C22 1.407(2) . ? C17 N3 1.447(2) . ? C18 C19 1.403(3) . ? C18 C23 1.514(3) . ? C19 C20 1.389(3) . ? C19 H19 0.9500 . ? C20 C21 1.390(3) . ? C20 C24 1.520(3) . ? C21 C22 1.396(3) . ? C21 H21 0.9500 . ? C22 C25 1.506(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C24 H24D 0.9800 . ? C24 H24E 0.9800 . ? C24 H24F 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N4 1.352(2) . ? C26 C27 1.387(2) . ? C26 H26 0.9500 . ? C27 C28 1.380(3) . ? C27 H27 0.9500 . ? C28 C29 1.393(3) . ? C28 H28 0.9500 . ? C29 C30 1.388(2) . ? C29 H29 0.9500 . ? C30 N4 1.356(2) . ? C30 C31 1.517(2) . ? C31 O2 1.229(2) . ? C31 O1 1.295(2) . ? N1 Ru1 1.9367(14) . ? N2 Ru1 2.1026(14) . ? N3 Ru1 2.0664(14) . ? N4 Ru1 2.0972(14) . ? O1 Ru1 2.0816(12) . ? Cl1 Ru1 2.3888(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 N1 C1 C2 120.36(16) . . ? N1 C1 C6 110.83(15) . . ? C2 C1 C6 128.80(16) . . ? C3 C2 C1 118.75(17) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C4 C3 C2 120.38(16) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.22(17) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 120.13(16) . . ? N1 C5 C16 111.78(15) . . ? C4 C5 C16 128.09(16) . . ? N2 C6 C1 118.25(16) . . ? N2 C6 H6 120.9 . . ? C1 C6 H6 120.9 . . ? C12 C7 C8 120.93(17) . . ? C12 C7 N2 120.46(16) . . ? C8 C7 N2 118.60(16) . . ? C9 C8 C7 118.30(18) . . ? C9 C8 C13 119.47(18) . . ? C7 C8 C13 122.14(17) . . ? C8 C9 C10 122.2(2) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 117.76(18) . . ? C11 C10 C14 121.6(2) . . ? C9 C10 C14 120.6(2) . . ? C10 C11 C12 122.72(19) . . ? C10 C11 H11 118.6 . . ? C12 C11 H11 118.6 . . ? C11 C12 C7 117.92(18) . . ? C11 C12 C15 118.43(17) . . ? C7 C12 C15 123.65(17) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C14 H14D 109.5 . . ? H14A C14 H14D 141.1 . . ? H14B C14 H14D 56.3 . . ? H14C C14 H14D 56.3 . . ? C10 C14 H14E 109.5 . . ? H14A C14 H14E 56.3 . . ? H14B C14 H14E 141.1 . . ? H14C C14 H14E 56.3 . . ? H14D C14 H14E 109.5 . . ? C10 C14 H14F 109.5 . . ? H14A C14 H14F 56.3 . . ? H14B C14 H14F 56.3 . . ? H14C C14 H14F 141.1 . . ? H14D C14 H14F 109.5 . . ? H14E C14 H14F 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 C5 116.37(16) . . ? N3 C16 H16 121.8 . . ? C5 C16 H16 121.8 . . ? C18 C17 C22 121.64(17) . . ? C18 C17 N3 119.52(15) . . ? C22 C17 N3 118.81(16) . . ? C17 C18 C19 117.52(17) . . ? C17 C18 C23 122.48(17) . . ? C19 C18 C23 120.00(18) . . ? C20 C19 C18 122.11(19) . . ? C20 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C19 C20 C21 118.70(18) . . ? C19 C20 C24 120.7(2) . . ? C21 C20 C24 120.7(2) . . ? C20 C21 C22 121.69(19) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C21 C22 C17 118.15(18) . . ? C21 C22 C25 120.25(18) . . ? C17 C22 C25 121.51(17) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C24 H24D 109.5 . . ? H24A C24 H24D 141.1 . . ? H24B C24 H24D 56.3 . . ? H24C C24 H24D 56.3 . . ? C20 C24 H24E 109.5 . . ? H24A C24 H24E 56.3 . . ? H24B C24 H24E 141.1 . . ? H24C C24 H24E 56.3 . . ? H24D C24 H24E 109.5 . . ? C20 C24 H24F 109.5 . . ? H24A C24 H24F 56.3 . . ? H24B C24 H24F 56.3 . . ? H24C C24 H24F 141.1 . . ? H24D C24 H24F 109.5 . . ? H24E C24 H24F 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N4 C26 C27 122.11(16) . . ? N4 C26 H26 118.9 . . ? C27 C26 H26 118.9 . . ? C28 C27 C26 119.76(16) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C29 118.56(16) . . ? C27 C28 H28 120.7 . . ? C29 C28 H28 120.7 . . ? C30 C29 C28 119.16(17) . . ? C30 C29 H29 120.4 . . ? C28 C29 H29 120.4 . . ? N4 C30 C29 122.21(15) . . ? N4 C30 C31 115.10(14) . . ? C29 C30 C31 122.68(16) . . ? O2 C31 O1 124.97(15) . . ? O2 C31 C30 120.43(15) . . ? O1 C31 C30 114.61(15) . . ? C5 N1 C1 121.14(14) . . ? C5 N1 Ru1 118.42(11) . . ? C1 N1 Ru1 119.40(11) . . ? C6 N2 C7 115.29(14) . . ? C6 N2 Ru1 112.10(12) . . ? C7 N2 Ru1 132.19(11) . . ? C16 N3 C17 118.74(15) . . ? C16 N3 Ru1 113.86(12) . . ? C17 N3 Ru1 126.90(11) . . ? C26 N4 C30 118.15(14) . . ? C26 N4 Ru1 127.42(12) . . ? C30 N4 Ru1 114.38(11) . . ? C31 O1 Ru1 117.54(10) . . ? N1 Ru1 N3 78.71(6) . . ? N1 Ru1 O1 102.45(5) . . ? N3 Ru1 O1 89.24(5) . . ? N1 Ru1 N4 177.27(6) . . ? N3 Ru1 N4 98.65(5) . . ? O1 Ru1 N4 78.10(5) . . ? N1 Ru1 N2 78.45(6) . . ? N3 Ru1 N2 156.34(6) . . ? O1 Ru1 N2 89.73(5) . . ? N4 Ru1 N2 104.25(5) . . ? N1 Ru1 Cl1 83.00(4) . . ? N3 Ru1 Cl1 92.89(4) . . ? O1 Ru1 Cl1 174.45(3) . . ? N4 Ru1 Cl1 96.51(4) . . ? N2 Ru1 Cl1 90.36(4) . . ? 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 C1 C2 C3 -1.3(3) . . . . ? C6 C1 C2 C3 179.65(17) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 N1 0.5(3) . . . . ? C3 C4 C5 C16 -179.91(17) . . . . ? N1 C1 C6 N2 4.8(2) . . . . ? C2 C1 C6 N2 -176.15(17) . . . . ? C12 C7 C8 C9 3.9(3) . . . . ? N2 C7 C8 C9 -174.98(17) . . . . ? C12 C7 C8 C13 -172.73(19) . . . . ? N2 C7 C8 C13 8.4(3) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C13 C8 C9 C10 176.8(2) . . . . ? C8 C9 C10 C11 -3.2(3) . . . . ? C8 C9 C10 C14 176.4(2) . . . . ? C9 C10 C11 C12 2.6(3) . . . . ? C14 C10 C11 C12 -177.0(2) . . . . ? C10 C11 C12 C7 1.3(3) . . . . ? C10 C11 C12 C15 -178.68(18) . . . . ? C8 C7 C12 C11 -4.6(3) . . . . ? N2 C7 C12 C11 174.33(16) . . . . ? C8 C7 C12 C15 175.38(17) . . . . ? N2 C7 C12 C15 -5.7(3) . . . . ? N1 C5 C16 N3 -6.0(2) . . . . ? C4 C5 C16 N3 174.36(17) . . . . ? C22 C17 C18 C19 3.6(3) . . . . ? N3 C17 C18 C19 -174.48(16) . . . . ? C22 C17 C18 C23 -176.30(18) . . . . ? N3 C17 C18 C23 5.6(3) . . . . ? C17 C18 C19 C20 0.1(3) . . . . ? C23 C18 C19 C20 180.00(19) . . . . ? C18 C19 C20 C21 -3.4(3) . . . . ? C18 C19 C20 C24 176.6(2) . . . . ? C19 C20 C21 C22 3.1(3) . . . . ? C24 C20 C21 C22 -176.9(2) . . . . ? C20 C21 C22 C17 0.4(3) . . . . ? C20 C21 C22 C25 -176.3(2) . . . . ? C18 C17 C22 C21 -3.9(3) . . . . ? N3 C17 C22 C21 174.21(16) . . . . ? C18 C17 C22 C25 172.79(18) . . . . ? N3 C17 C22 C25 -9.1(3) . . . . ? N4 C26 C27 C28 -0.6(3) . . . . ? C26 C27 C28 C29 1.4(3) . . . . ? C27 C28 C29 C30 -0.3(3) . . . . ? C28 C29 C30 N4 -1.6(3) . . . . ? C28 C29 C30 C31 179.21(17) . . . . ? N4 C30 C31 O2 176.53(16) . . . . ? C29 C30 C31 O2 -4.2(3) . . . . ? N4 C30 C31 O1 -3.4(2) . . . . ? C29 C30 C31 O1 175.87(17) . . . . ? C4 C5 N1 C1 -1.7(2) . . . . ? C16 C5 N1 C1 178.63(15) . . . . ? C4 C5 N1 Ru1 -169.98(13) . . . . ? C16 C5 N1 Ru1 10.37(19) . . . . ? C2 C1 N1 C5 2.1(2) . . . . ? C6 C1 N1 C5 -178.68(15) . . . . ? C2 C1 N1 Ru1 170.30(13) . . . . ? C6 C1 N1 Ru1 -10.53(19) . . . . ? C1 C6 N2 C7 -171.15(15) . . . . ? C1 C6 N2 Ru1 2.3(2) . . . . ? C12 C7 N2 C6 -115.85(18) . . . . ? C8 C7 N2 C6 63.1(2) . . . . ? C12 C7 N2 Ru1 72.3(2) . . . . ? C8 C7 N2 Ru1 -108.75(18) . . . . ? C5 C16 N3 C17 171.93(15) . . . . ? C5 C16 N3 Ru1 -0.5(2) . . . . ? C18 C17 N3 C16 -72.2(2) . . . . ? C22 C17 N3 C16 109.71(19) . . . . ? C18 C17 N3 Ru1 99.20(17) . . . . ? C22 C17 N3 Ru1 -78.93(19) . . . . ? C27 C26 N4 C30 -1.3(3) . . . . ? C27 C26 N4 Ru1 -178.77(13) . . . . ? C29 C30 N4 C26 2.4(3) . . . . ? C31 C30 N4 C26 -178.35(15) . . . . ? C29 C30 N4 Ru1 -179.82(14) . . . . ? C31 C30 N4 Ru1 -0.57(19) . . . . ? O2 C31 O1 Ru1 -174.14(14) . . . . ? C30 C31 O1 Ru1 5.75(19) . . . . ? C5 N1 Ru1 N3 -8.40(12) . . . . ? C1 N1 Ru1 N3 -176.88(13) . . . . ? C5 N1 Ru1 O1 -95.08(12) . . . . ? C1 N1 Ru1 O1 96.45(13) . . . . ? C5 N1 Ru1 N2 177.79(13) . . . . ? C1 N1 Ru1 N2 9.31(12) . . . . ? C5 N1 Ru1 Cl1 85.98(12) . . . . ? C1 N1 Ru1 Cl1 -82.50(12) . . . . ? C16 N3 Ru1 N1 4.65(12) . . . . ? C17 N3 Ru1 N1 -167.08(15) . . . . ? C16 N3 Ru1 O1 107.50(12) . . . . ? C17 N3 Ru1 O1 -64.22(14) . . . . ? C16 N3 Ru1 N4 -174.66(12) . . . . ? C17 N3 Ru1 N4 13.62(14) . . . . ? C16 N3 Ru1 N2 19.9(2) . . . . ? C17 N3 Ru1 N2 -151.81(14) . . . . ? C16 N3 Ru1 Cl1 -77.62(12) . . . . ? C17 N3 Ru1 Cl1 110.65(13) . . . . ? C31 O1 Ru1 N1 172.51(12) . . . . ? C31 O1 Ru1 N3 94.26(12) . . . . ? C31 O1 Ru1 N4 -4.75(12) . . . . ? C31 O1 Ru1 N2 -109.38(12) . . . . ? C26 N4 Ru1 N3 92.77(15) . . . . ? C30 N4 Ru1 N3 -84.77(12) . . . . ? C26 N4 Ru1 O1 -179.85(15) . . . . ? C30 N4 Ru1 O1 2.61(11) . . . . ? C26 N4 Ru1 N2 -93.20(15) . . . . ? C30 N4 Ru1 N2 89.26(12) . . . . ? C26 N4 Ru1 Cl1 -1.17(14) . . . . ? C30 N4 Ru1 Cl1 -178.71(11) . . . . ? C6 N2 Ru1 N1 -6.00(12) . . . . ? C7 N2 Ru1 N1 166.00(16) . . . . ? C6 N2 Ru1 N3 -21.3(2) . . . . ? C7 N2 Ru1 N3 150.72(15) . . . . ? C6 N2 Ru1 O1 -108.77(12) . . . . ? C7 N2 Ru1 O1 63.23(15) . . . . ? C6 N2 Ru1 N4 173.58(12) . . . . ? C7 N2 Ru1 N4 -14.42(16) . . . . ? C6 N2 Ru1 Cl1 76.78(12) . . . . ? C7 N2 Ru1 Cl1 -111.22(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.399 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 880797'