# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'P C McGowan' 'Kenneth Camm' 'Ahmed El-Sokkary' 'Andrew L Gott' 'Peter Stockley' _publ_contact_author_name 'P C McGowan' _publ_contact_author_email P.C.MCGOWAN@CHEM.LEEDS.AC.UK _publ_section_title ; Synthesis, molecular structure and evaluation of new organometallic ruthenium anticancer agents ; # Attachment 'compound1.CIF' data_kcru1 _database_code_depnum_ccdc_archive 'CCDC 752541' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Cl N O2 Ru' _chemical_formula_weight 392.83 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' 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 P21/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 10.0453(3) _cell_length_b 15.1265(4) _cell_length_c 10.3023(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.401(2) _cell_angle_gamma 90.00 _cell_volume 1544.41(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20308 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 1.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7967 _exptl_absorpt_correction_T_max 0.8902 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17013 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3035 _reflns_number_gt 2736 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0367P)^2^+1.0829P] 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 SHELXL _refine_ls_extinction_coef 0.0050(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3035 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.212454(18) 0.199245(13) 0.545764(17) 0.02544(11) Uani 1 1 d . . . Cl1 Cl 0.39880(6) 0.14919(4) 0.44376(6) 0.03398(16) Uani 1 1 d . . . N1 N 0.2158(2) 0.30939(13) 0.4229(2) 0.0258(4) Uani 1 1 d . . . O1 O 0.35352(17) 0.28048(11) 0.65855(16) 0.0296(4) Uani 1 1 d . . . O2 O 0.4790(2) 0.40139(14) 0.65326(18) 0.0431(5) Uani 1 1 d . . . C11 C 0.3893(2) 0.35102(17) 0.6030(2) 0.0292(5) Uani 1 1 d . . . C2 C -0.0891(3) 0.29632(18) 0.5229(3) 0.0380(6) Uani 1 1 d . . . H2 H -0.0986 0.3037 0.4254 0.046 Uiso 1 1 calc R . . C4 C -0.0010(3) 0.21633(18) 0.5606(3) 0.0310(5) Uani 1 1 d . . . C14 C 0.2386(3) 0.46461(18) 0.2844(3) 0.0326(6) Uani 1 1 d . . . H14 H 0.2454 0.5181 0.2375 0.039 Uiso 1 1 calc R . . C12 C 0.3085(2) 0.37099(17) 0.4703(2) 0.0269(5) Uani 1 1 d . . . C10 C 0.0740(3) 0.20355(17) 0.6873(3) 0.0335(6) Uani 1 1 d . . . H10 H 0.0670 0.2454 0.7547 0.040 Uiso 1 1 calc R . . C5 C 0.0130(2) 0.15103(17) 0.4626(2) 0.0314(5) Uani 1 1 d . . . H5 H -0.0377 0.1571 0.3767 0.038 Uiso 1 1 calc R . . C15 C 0.1443(3) 0.40111(18) 0.2359(2) 0.0319(5) Uani 1 1 d . . . H15 H 0.0853 0.4104 0.1551 0.038 Uiso 1 1 calc R . . C6 C 0.0997(3) 0.07848(18) 0.4907(3) 0.0347(6) Uani 1 1 d . . . H6 H 0.1084 0.0372 0.4231 0.042 Uiso 1 1 calc R . . C9 C 0.1601(3) 0.12881(18) 0.7158(3) 0.0368(6) Uani 1 1 d . . . H9 H 0.2085 0.1217 0.8024 0.044 Uiso 1 1 calc R . . C13 C 0.3233(3) 0.44869(17) 0.4031(2) 0.0317(5) Uani 1 1 d . . . H13 H 0.3902 0.4906 0.4376 0.038 Uiso 1 1 calc R . . C16 C 0.1367(2) 0.32368(18) 0.3065(2) 0.0286(5) Uani 1 1 d . . . H16 H 0.0737 0.2795 0.2716 0.034 Uiso 1 1 calc R . . C7 C 0.1757(3) 0.06550(18) 0.6202(3) 0.0365(6) Uani 1 1 d . . . C1 C -0.0320(3) 0.3821(2) 0.5861(3) 0.0495(8) Uani 1 1 d . . . H1A H -0.0304 0.3792 0.6813 0.074 Uiso 1 1 calc R . . H1B H -0.0888 0.4317 0.5495 0.074 Uiso 1 1 calc R . . H1C H 0.0600 0.3907 0.5681 0.074 Uiso 1 1 calc R . . C8 C 0.2753(3) -0.0087(2) 0.6478(3) 0.0504(8) Uani 1 1 d . . . H8A H 0.3432 0.0063 0.7242 0.076 Uiso 1 1 calc R . . H8B H 0.3198 -0.0182 0.5710 0.076 Uiso 1 1 calc R . . H8C H 0.2281 -0.0629 0.6662 0.076 Uiso 1 1 calc R . . C3 C -0.2305(3) 0.2784(2) 0.5560(3) 0.0484(7) Uani 1 1 d . . . H3A H -0.2659 0.2232 0.5138 0.073 Uiso 1 1 calc R . . H3B H -0.2908 0.3274 0.5238 0.073 Uiso 1 1 calc R . . H3C H -0.2249 0.2730 0.6516 0.073 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 0.02411(14) 0.02762(15) 0.02338(14) 0.00159(7) 0.00029(8) -0.00510(7) Cl1 0.0294(3) 0.0378(4) 0.0344(3) -0.0002(2) 0.0041(2) 0.0004(3) N1 0.0231(10) 0.0302(11) 0.0240(10) -0.0003(8) 0.0032(8) -0.0023(8) O1 0.0300(9) 0.0308(9) 0.0260(9) 0.0040(7) -0.0014(7) -0.0077(7) O2 0.0410(11) 0.0476(12) 0.0360(10) 0.0077(8) -0.0082(8) -0.0221(9) C11 0.0258(12) 0.0337(14) 0.0275(12) 0.0013(10) 0.0023(10) -0.0045(10) C2 0.0321(14) 0.0472(17) 0.0366(15) 0.0079(11) 0.0111(12) 0.0028(11) C4 0.0258(13) 0.0374(14) 0.0307(13) 0.0019(10) 0.0070(10) -0.0057(11) C14 0.0327(13) 0.0343(14) 0.0313(13) 0.0080(10) 0.0065(10) 0.0030(11) C12 0.0240(12) 0.0311(13) 0.0254(11) 0.0022(9) 0.0030(9) -0.0018(10) C10 0.0350(14) 0.0420(16) 0.0243(12) 0.0009(10) 0.0070(11) -0.0084(11) C5 0.0274(13) 0.0388(15) 0.0272(12) 0.0001(10) 0.0022(10) -0.0118(11) C15 0.0281(13) 0.0407(15) 0.0262(12) 0.0027(10) 0.0024(10) 0.0036(11) C6 0.0321(14) 0.0346(14) 0.0376(14) -0.0042(11) 0.0062(11) -0.0110(11) C9 0.0352(14) 0.0442(16) 0.0293(13) 0.0107(11) 0.0009(11) -0.0118(12) C13 0.0285(13) 0.0324(13) 0.0341(13) 0.0045(10) 0.0052(10) -0.0051(10) C16 0.0236(12) 0.0364(13) 0.0251(12) -0.0014(10) 0.0022(9) -0.0009(10) C7 0.0329(14) 0.0304(14) 0.0450(15) 0.0085(11) 0.0033(11) -0.0093(11) C1 0.0508(18) 0.0368(16) 0.067(2) 0.0023(14) 0.0272(16) 0.0052(14) C8 0.0444(17) 0.0345(16) 0.070(2) 0.0158(14) 0.0033(15) -0.0017(13) C3 0.0343(16) 0.062(2) 0.0512(18) 0.0111(15) 0.0150(13) 0.0022(14) _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 O1 2.0809(17) . ? Ru1 N1 2.096(2) . ? Ru1 C5 2.173(2) . ? Ru1 C10 2.175(3) . ? Ru1 C6 2.175(3) . ? Ru1 C9 2.186(2) . ? Ru1 C4 2.190(3) . ? Ru1 C7 2.216(3) . ? Ru1 Cl1 2.4133(6) . ? N1 C16 1.343(3) . ? N1 C12 1.351(3) . ? O1 C11 1.290(3) . ? O2 C11 1.228(3) . ? C11 C12 1.502(3) . ? C2 C4 1.512(4) . ? C2 C1 1.521(4) . ? C2 C3 1.538(4) . ? C4 C10 1.410(4) . ? C4 C5 1.436(4) . ? C14 C15 1.384(4) . ? C14 C13 1.392(4) . ? C12 C13 1.384(4) . ? C10 C9 1.425(4) . ? C5 C6 1.402(4) . ? C15 C16 1.388(4) . ? C6 C7 1.438(4) . ? C9 C7 1.401(4) . ? C7 C8 1.500(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 O1 Ru1 N1 77.95(7) . . ? O1 Ru1 C5 156.71(9) . . ? N1 Ru1 C5 97.67(9) . . ? O1 Ru1 C10 93.42(8) . . ? N1 Ru1 C10 117.16(9) . . ? C5 Ru1 C10 67.97(10) . . ? O1 Ru1 C6 156.86(9) . . ? N1 Ru1 C6 124.69(9) . . ? C5 Ru1 C6 37.62(10) . . ? C10 Ru1 C6 80.62(10) . . ? O1 Ru1 C9 94.10(8) . . ? N1 Ru1 C9 154.28(9) . . ? C5 Ru1 C9 79.95(9) . . ? C10 Ru1 C9 38.13(10) . . ? C6 Ru1 C9 67.45(10) . . ? O1 Ru1 C4 118.47(9) . . ? N1 Ru1 C4 93.50(9) . . ? C5 Ru1 C4 38.43(10) . . ? C10 Ru1 C4 37.70(10) . . ? C6 Ru1 C4 69.09(10) . . ? C9 Ru1 C4 68.61(10) . . ? O1 Ru1 C7 118.86(9) . . ? N1 Ru1 C7 162.70(9) . . ? C5 Ru1 C7 68.60(10) . . ? C10 Ru1 C7 68.56(10) . . ? C6 Ru1 C7 38.22(10) . . ? C9 Ru1 C7 37.10(10) . . ? C4 Ru1 C7 82.15(10) . . ? O1 Ru1 Cl1 85.56(5) . . ? N1 Ru1 Cl1 84.04(6) . . ? C5 Ru1 Cl1 116.99(7) . . ? C10 Ru1 Cl1 158.14(7) . . ? C6 Ru1 Cl1 91.77(7) . . ? C9 Ru1 Cl1 120.08(8) . . ? C4 Ru1 Cl1 154.88(7) . . ? C7 Ru1 Cl1 92.81(8) . . ? C16 N1 C12 119.0(2) . . ? C16 N1 Ru1 126.95(17) . . ? C12 N1 Ru1 114.08(16) . . ? C11 O1 Ru1 117.04(15) . . ? O2 C11 O1 124.4(2) . . ? O2 C11 C12 120.6(2) . . ? O1 C11 C12 115.0(2) . . ? C4 C2 C1 114.1(3) . . ? C4 C2 C3 108.9(2) . . ? C1 C2 C3 110.7(3) . . ? C10 C4 C5 117.3(2) . . ? C10 C4 C2 123.3(2) . . ? C5 C4 C2 119.4(2) . . ? C10 C4 Ru1 70.56(15) . . ? C5 C4 Ru1 70.15(14) . . ? C2 C4 Ru1 127.98(18) . . ? C15 C14 C13 118.8(2) . . ? N1 C12 C13 121.9(2) . . ? N1 C12 C11 115.4(2) . . ? C13 C12 C11 122.7(2) . . ? C4 C10 C9 120.9(2) . . ? C4 C10 Ru1 71.74(14) . . ? C9 C10 Ru1 71.38(15) . . ? C6 C5 C4 121.5(2) . . ? C6 C5 Ru1 71.28(14) . . ? C4 C5 Ru1 71.42(14) . . ? C14 C15 C16 119.3(2) . . ? C5 C6 C7 121.1(2) . . ? C5 C6 Ru1 71.10(14) . . ? C7 C6 Ru1 72.41(14) . . ? C7 C9 C10 122.1(2) . . ? C7 C9 Ru1 72.58(14) . . ? C10 C9 Ru1 70.48(14) . . ? C12 C13 C14 119.1(2) . . ? N1 C16 C15 121.9(2) . . ? C9 C7 C6 117.1(2) . . ? C9 C7 C8 121.8(3) . . ? C6 C7 C8 121.0(3) . . ? C9 C7 Ru1 70.31(14) . . ? C6 C7 Ru1 69.37(14) . . ? C8 C7 Ru1 127.27(19) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.386 _refine_diff_density_min -0.822 _refine_diff_density_rms 0.102 # Attachment 'compound2.CIF' data_kcrulig4 _database_code_depnum_ccdc_archive 'CCDC 752542' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 Cl N3 O3 Ru' _chemical_formula_weight 512.95 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.444(6) _cell_length_b 8.5608(17) _cell_length_c 16.642(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.19(3) _cell_angle_gamma 90.00 _cell_volume 4118.0(16) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 18394 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description fragment _exptl_crystal_colour orange _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.921 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7633 _exptl_absorpt_correction_T_max 0.8975 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38. ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10983 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4001 _reflns_number_gt 3108 _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/[\s^2^(Fo^2^)+(0.0282P)^2^+8.8714P] 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 4001 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 C3 C 0.1880(2) -0.0794(7) 0.5263(4) 0.087(2) Uani 1 1 d . . . H3A H 0.1948 -0.1907 0.5385 0.130 Uiso 1 1 calc R . . H3B H 0.1630 -0.0485 0.5442 0.130 Uiso 1 1 calc R . . H3C H 0.2158 -0.0180 0.5589 0.130 Uiso 1 1 calc R . . C1 C 0.2114(3) -0.0900(8) 0.4023(5) 0.137(4) Uani 1 1 d . . . H1A H 0.2009 -0.0685 0.3396 0.205 Uiso 1 1 calc R . . H1B H 0.2194 -0.2009 0.4131 0.205 Uiso 1 1 calc R . . H1C H 0.2387 -0.0263 0.4345 0.205 Uiso 1 1 calc R . . C2 C 0.17365(17) -0.0510(5) 0.4322(3) 0.0547(12) Uani 1 1 d . . . H2 H 0.1478 -0.1253 0.4016 0.066 Uiso 1 1 calc R . . C19 C 0.19393(14) 0.4471(6) 0.7350(3) 0.0491(11) Uani 1 1 d . . . H19 H 0.2200 0.4262 0.7875 0.059 Uiso 1 1 calc R . . C20 C 0.18034(14) 0.5985(5) 0.7107(3) 0.0422(10) Uani 1 1 d . . . C11 C 0.03908(13) -0.0664(4) 0.3647(3) 0.0386(9) Uani 1 1 d . . . H11 H 0.0373 -0.0445 0.3075 0.046 Uiso 1 1 calc R . . C17 C 0.13079(12) 0.3565(5) 0.6054(2) 0.0333(9) Uani 1 1 d . . . C12 C 0.01712(14) -0.1970(5) 0.3783(3) 0.0432(10) Uani 1 1 d . . . H12 H 0.0008 -0.2646 0.3308 0.052 Uiso 1 1 calc R . . C10 C 0.09092(16) 0.5655(5) 0.3059(3) 0.0520(12) Uani 1 1 d . . . H10A H 0.0971 0.6358 0.3557 0.078 Uiso 1 1 calc R . . H10B H 0.0575 0.5493 0.2759 0.078 Uiso 1 1 calc R . . H10C H 0.1029 0.6120 0.2652 0.078 Uiso 1 1 calc R . . C9 C 0.11800(13) 0.1296(4) 0.3180(2) 0.0349(9) Uani 1 1 d . . . H9 H 0.1070 0.0399 0.2821 0.042 Uiso 1 1 calc R . . C21 C 0.14261(14) 0.6325(5) 0.6357(2) 0.0407(10) Uani 1 1 d . . . H21 H 0.1336 0.7378 0.6201 0.049 Uiso 1 1 calc R . . O2 O 0.19891(12) 0.8602(5) 0.7361(2) 0.0682(10) Uani 1 1 d . . . O3 O 0.23560(11) 0.6952(5) 0.8388(2) 0.0706(10) Uani 1 1 d . . . C4 C 0.15483(13) 0.1121(4) 0.4017(2) 0.0339(8) Uani 1 1 d . . . C7 C 0.11428(13) 0.4115(4) 0.3379(2) 0.0337(8) Uani 1 1 d . . . C18 C 0.16910(13) 0.3241(5) 0.6820(3) 0.0435(10) Uani 1 1 d . . . H18 H 0.1783 0.2190 0.6981 0.052 Uiso 1 1 calc R . . C22 C 0.11786(14) 0.5111(5) 0.5833(2) 0.0378(9) Uani 1 1 d . . . H22 H 0.0916 0.5337 0.5314 0.045 Uiso 1 1 calc R . . C8 C 0.09759(13) 0.2736(4) 0.2871(2) 0.0332(8) Uani 1 1 d . . . H8 H 0.0724 0.2801 0.2318 0.040 Uiso 1 1 calc R . . C15 C 0.06445(12) 0.0002(4) 0.5112(2) 0.0313(8) Uani 1 1 d . . . C5 C 0.17059(12) 0.2481(4) 0.4516(2) 0.0345(9) Uani 1 1 d . . . H5 H 0.1949 0.2407 0.5080 0.041 Uiso 1 1 calc R . . C13 C 0.01881(15) -0.2296(4) 0.4601(3) 0.0448(11) Uani 1 1 d . . . H13 H 0.0038 -0.3193 0.4701 0.054 Uiso 1 1 calc R . . C14 C 0.04280(13) -0.1290(4) 0.5276(3) 0.0392(9) Uani 1 1 d . . . H14 H 0.0444 -0.1486 0.5849 0.047 Uiso 1 1 calc R . . C16 C 0.08986(12) 0.1168(4) 0.5803(2) 0.0326(8) Uani 1 1 d . . . C6 C 0.15106(13) 0.3965(4) 0.4198(2) 0.0352(9) Uani 1 1 d . . . H6 H 0.1631 0.4869 0.4544 0.042 Uiso 1 1 calc R . . O1 O 0.09280(10) 0.0993(3) 0.65644(16) 0.0458(7) Uani 1 1 d . . . N1 N 0.06304(10) 0.0308(3) 0.43050(19) 0.0297(7) Uani 1 1 d . . . N2 N 0.10588(10) 0.2361(3) 0.54844(18) 0.0300(7) Uani 1 1 d . . . N3 N 0.20713(12) 0.7286(5) 0.7649(3) 0.0497(10) Uani 1 1 d . . . Cl1 Cl 0.02345(3) 0.35984(10) 0.38449(6) 0.0330(2) Uani 1 1 d . . . Ru1 Ru 0.096900(9) 0.23187(3) 0.417030(17) 0.02560(11) 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 C3 0.122(5) 0.077(4) 0.086(4) 0.044(3) 0.068(4) 0.054(4) C1 0.208(8) 0.128(6) 0.144(6) 0.094(5) 0.144(6) 0.134(6) C2 0.059(3) 0.046(3) 0.060(3) 0.011(2) 0.024(2) 0.017(2) C19 0.027(2) 0.076(3) 0.038(2) -0.015(2) 0.0056(19) 0.012(2) C20 0.034(2) 0.053(3) 0.046(2) -0.020(2) 0.023(2) -0.008(2) C11 0.042(2) 0.036(2) 0.040(2) -0.0034(17) 0.0188(19) -0.0013(18) C17 0.031(2) 0.047(2) 0.0237(19) -0.0023(15) 0.0132(16) 0.0038(17) C12 0.042(2) 0.034(2) 0.060(3) -0.0095(19) 0.027(2) -0.0077(18) C10 0.057(3) 0.039(2) 0.071(3) 0.027(2) 0.039(3) 0.013(2) C9 0.040(2) 0.036(2) 0.036(2) -0.0085(16) 0.0218(18) -0.0016(17) C21 0.045(2) 0.043(2) 0.038(2) -0.0107(17) 0.021(2) -0.0047(19) O2 0.069(2) 0.069(3) 0.073(2) -0.0255(19) 0.034(2) -0.024(2) O3 0.0408(19) 0.102(3) 0.063(2) -0.034(2) 0.0130(18) -0.0116(18) C4 0.034(2) 0.034(2) 0.038(2) 0.0057(16) 0.0183(18) 0.0045(17) C7 0.036(2) 0.034(2) 0.039(2) 0.0108(16) 0.0230(18) 0.0050(17) C18 0.037(2) 0.055(3) 0.035(2) -0.0069(19) 0.0110(19) 0.012(2) C22 0.039(2) 0.044(2) 0.030(2) -0.0021(16) 0.0125(18) -0.0002(18) C8 0.033(2) 0.045(2) 0.0242(18) 0.0032(15) 0.0139(16) 0.0012(17) C15 0.030(2) 0.0297(19) 0.038(2) 0.0070(15) 0.0177(17) 0.0077(15) C5 0.0245(18) 0.050(2) 0.0289(19) 0.0021(16) 0.0100(15) 0.0001(17) C13 0.045(2) 0.025(2) 0.078(3) 0.0019(19) 0.039(2) 0.0003(18) C14 0.046(2) 0.029(2) 0.054(3) 0.0130(18) 0.032(2) 0.0099(18) C16 0.032(2) 0.036(2) 0.032(2) 0.0089(16) 0.0147(17) 0.0088(16) C6 0.042(2) 0.031(2) 0.043(2) -0.0071(16) 0.0275(19) -0.0104(17) O1 0.0551(18) 0.0554(18) 0.0310(15) 0.0123(12) 0.0215(14) 0.0035(14) N1 0.0318(17) 0.0268(16) 0.0333(17) 0.0013(12) 0.0159(14) 0.0033(13) N2 0.0325(16) 0.0354(17) 0.0237(15) 0.0011(12) 0.0126(13) 0.0015(13) N3 0.033(2) 0.073(3) 0.047(2) -0.024(2) 0.0186(18) -0.0114(19) Cl1 0.0307(5) 0.0350(5) 0.0343(5) 0.0046(4) 0.0140(4) 0.0037(4) Ru1 0.02833(17) 0.02613(17) 0.02314(16) 0.00098(11) 0.01099(12) 0.00047(12) _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 C3 C2 1.470(6) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C1 C2 1.495(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C4 1.523(5) . ? C2 H2 1.0000 . ? C19 C20 1.375(6) . ? C19 C18 1.398(6) . ? C19 H19 0.9500 . ? C20 C21 1.372(6) . ? C20 N3 1.472(5) . ? C11 N1 1.345(5) . ? C11 C12 1.379(5) . ? C11 H11 0.9500 . ? C17 C22 1.391(5) . ? C17 C18 1.394(5) . ? C17 N2 1.411(5) . ? C12 C13 1.370(6) . ? C12 H12 0.9500 . ? C10 C7 1.501(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C9 C8 1.392(5) . ? C9 C4 1.426(5) . ? C9 Ru1 2.187(3) . ? C9 H9 0.9500 . ? C21 C22 1.383(5) . ? C21 H21 0.9500 . ? O2 N3 1.211(5) . ? O3 N3 1.236(5) . ? C4 C5 1.402(5) . ? C4 Ru1 2.191(4) . ? C7 C6 1.404(5) . ? C7 C8 1.426(5) . ? C7 Ru1 2.229(3) . ? C18 H18 0.9500 . ? C22 H22 0.9500 . ? C8 Ru1 2.200(3) . ? C8 H8 0.9500 . ? C15 N1 1.353(4) . ? C15 C14 1.381(5) . ? C15 C16 1.494(5) . ? C5 C6 1.420(5) . ? C5 Ru1 2.161(4) . ? C5 H5 0.9500 . ? C13 C14 1.380(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 O1 1.243(4) . ? C16 N2 1.337(5) . ? C6 Ru1 2.197(4) . ? C6 H6 0.9500 . ? N1 Ru1 2.082(3) . ? N2 Ru1 2.092(3) . ? Cl1 Ru1 2.4171(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 C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? 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 . . ? C3 C2 C1 111.5(5) . . ? C3 C2 C4 115.0(4) . . ? C1 C2 C4 110.5(4) . . ? C3 C2 H2 106.4 . . ? C1 C2 H2 106.4 . . ? C4 C2 H2 106.4 . . ? C20 C19 C18 119.5(4) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 121.7(4) . . ? C21 C20 N3 118.6(4) . . ? C19 C20 N3 119.8(4) . . ? N1 C11 C12 121.6(4) . . ? N1 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C22 C17 C18 119.2(4) . . ? C22 C17 N2 119.4(3) . . ? C18 C17 N2 121.4(3) . . ? C13 C12 C11 120.1(4) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C9 C4 122.2(3) . . ? C8 C9 Ru1 72.0(2) . . ? C4 C9 Ru1 71.1(2) . . ? C8 C9 H9 118.9 . . ? C4 C9 H9 118.9 . . ? Ru1 C9 H9 130.9 . . ? C20 C21 C22 119.0(4) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C5 C4 C9 116.9(3) . . ? C5 C4 C2 124.3(4) . . ? C9 C4 C2 118.7(3) . . ? C5 C4 Ru1 70.0(2) . . ? C9 C4 Ru1 70.9(2) . . ? C2 C4 Ru1 128.5(3) . . ? C6 C7 C8 118.0(3) . . ? C6 C7 C10 121.7(4) . . ? C8 C7 C10 120.2(4) . . ? C6 C7 Ru1 70.3(2) . . ? C8 C7 Ru1 70.2(2) . . ? C10 C7 Ru1 128.0(3) . . ? C17 C18 C19 119.6(4) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C21 C22 C17 121.0(4) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? C9 C8 C7 120.4(3) . . ? C9 C8 Ru1 71.0(2) . . ? C7 C8 Ru1 72.3(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? Ru1 C8 H8 129.3 . . ? N1 C15 C14 121.6(4) . . ? N1 C15 C16 115.7(3) . . ? C14 C15 C16 122.7(3) . . ? C4 C5 C6 121.4(3) . . ? C4 C5 Ru1 72.4(2) . . ? C6 C5 Ru1 72.4(2) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? Ru1 C5 H5 128.3 . . ? C12 C13 C14 118.5(4) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C13 C14 C15 119.6(4) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? O1 C16 N2 127.5(4) . . ? O1 C16 C15 120.4(3) . . ? N2 C16 C15 112.1(3) . . ? C7 C6 C5 120.9(3) . . ? C7 C6 Ru1 72.7(2) . . ? C5 C6 Ru1 69.6(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? Ru1 C6 H6 130.9 . . ? C11 N1 C15 118.5(3) . . ? C11 N1 Ru1 124.7(3) . . ? C15 N1 Ru1 116.7(2) . . ? C16 N2 C17 119.2(3) . . ? C16 N2 Ru1 119.0(2) . . ? C17 N2 Ru1 121.7(2) . . ? O2 N3 O3 124.5(4) . . ? O2 N3 C20 118.7(4) . . ? O3 N3 C20 116.8(4) . . ? N1 Ru1 N2 76.46(11) . . ? N1 Ru1 C5 124.38(12) . . ? N2 Ru1 C5 91.78(13) . . ? N1 Ru1 C9 94.01(13) . . ? N2 Ru1 C9 146.96(13) . . ? C5 Ru1 C9 67.35(14) . . ? N1 Ru1 C4 96.29(12) . . ? N2 Ru1 C4 110.69(13) . . ? C5 Ru1 C4 37.59(13) . . ? C9 Ru1 C4 38.02(13) . . ? N1 Ru1 C6 162.39(13) . . ? N2 Ru1 C6 100.53(13) . . ? C5 Ru1 C6 38.02(13) . . ? C9 Ru1 C6 79.05(14) . . ? C4 Ru1 C6 68.25(14) . . ? N1 Ru1 C8 116.32(13) . . ? N2 Ru1 C8 167.16(13) . . ? C5 Ru1 C8 80.04(14) . . ? C9 Ru1 C8 36.98(13) . . ? C4 Ru1 C8 68.36(14) . . ? C6 Ru1 C8 66.97(14) . . ? N1 Ru1 C7 152.75(13) . . ? N2 Ru1 C7 129.98(13) . . ? C5 Ru1 C7 68.06(14) . . ? C9 Ru1 C7 67.24(14) . . ? C4 Ru1 C7 81.11(13) . . ? C6 Ru1 C7 36.98(14) . . ? C8 Ru1 C7 37.56(13) . . ? N1 Ru1 Cl1 85.11(8) . . ? N2 Ru1 Cl1 87.14(9) . . ? C5 Ru1 Cl1 149.36(10) . . ? C9 Ru1 Cl1 124.00(10) . . ? C4 Ru1 Cl1 161.97(10) . . ? C6 Ru1 Cl1 112.23(10) . . ? C8 Ru1 Cl1 94.85(10) . . ? C7 Ru1 Cl1 89.42(10) . . ? 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 C18 C19 C20 C21 0.5(6) . . . . ? C18 C19 C20 N3 -178.2(4) . . . . ? N1 C11 C12 C13 0.9(6) . . . . ? C19 C20 C21 C22 -0.3(6) . . . . ? N3 C20 C21 C22 178.5(3) . . . . ? C8 C9 C4 C5 -1.4(5) . . . . ? Ru1 C9 C4 C5 -54.4(3) . . . . ? C8 C9 C4 C2 177.2(4) . . . . ? Ru1 C9 C4 C2 124.1(3) . . . . ? C8 C9 C4 Ru1 53.1(3) . . . . ? C3 C2 C4 C5 34.0(6) . . . . ? C1 C2 C4 C5 -93.3(6) . . . . ? C3 C2 C4 C9 -144.4(4) . . . . ? C1 C2 C4 C9 88.3(6) . . . . ? C3 C2 C4 Ru1 -56.8(6) . . . . ? C1 C2 C4 Ru1 175.9(4) . . . . ? C22 C17 C18 C19 -0.3(6) . . . . ? N2 C17 C18 C19 177.5(4) . . . . ? C20 C19 C18 C17 -0.3(6) . . . . ? C20 C21 C22 C17 -0.3(6) . . . . ? C18 C17 C22 C21 0.5(6) . . . . ? N2 C17 C22 C21 -177.3(3) . . . . ? C4 C9 C8 C7 2.2(5) . . . . ? Ru1 C9 C8 C7 54.9(3) . . . . ? C4 C9 C8 Ru1 -52.7(3) . . . . ? C6 C7 C8 C9 -1.1(5) . . . . ? C10 C7 C8 C9 -177.5(3) . . . . ? Ru1 C7 C8 C9 -54.3(3) . . . . ? C6 C7 C8 Ru1 53.2(3) . . . . ? C10 C7 C8 Ru1 -123.2(3) . . . . ? C9 C4 C5 C6 -0.6(5) . . . . ? C2 C4 C5 C6 -179.1(4) . . . . ? Ru1 C4 C5 C6 -55.5(3) . . . . ? C9 C4 C5 Ru1 54.8(3) . . . . ? C2 C4 C5 Ru1 -123.6(4) . . . . ? C11 C12 C13 C14 0.0(6) . . . . ? C12 C13 C14 C15 -0.3(6) . . . . ? N1 C15 C14 C13 -0.4(6) . . . . ? C16 C15 C14 C13 178.1(3) . . . . ? N1 C15 C16 O1 179.6(3) . . . . ? C14 C15 C16 O1 0.9(5) . . . . ? N1 C15 C16 N2 1.9(4) . . . . ? C14 C15 C16 N2 -176.7(3) . . . . ? C8 C7 C6 C5 -0.9(5) . . . . ? C10 C7 C6 C5 175.5(3) . . . . ? Ru1 C7 C6 C5 52.3(3) . . . . ? C8 C7 C6 Ru1 -53.2(3) . . . . ? C10 C7 C6 Ru1 123.2(3) . . . . ? C4 C5 C6 C7 1.8(5) . . . . ? Ru1 C5 C6 C7 -53.7(3) . . . . ? C4 C5 C6 Ru1 55.5(3) . . . . ? C12 C11 N1 C15 -1.5(5) . . . . ? C12 C11 N1 Ru1 -179.4(3) . . . . ? C14 C15 N1 C11 1.3(5) . . . . ? C16 C15 N1 C11 -177.4(3) . . . . ? C14 C15 N1 Ru1 179.3(3) . . . . ? C16 C15 N1 Ru1 0.7(4) . . . . ? O1 C16 N2 C17 2.6(6) . . . . ? C15 C16 N2 C17 -179.9(3) . . . . ? O1 C16 N2 Ru1 178.8(3) . . . . ? C15 C16 N2 Ru1 -3.7(4) . . . . ? C22 C17 N2 C16 -128.7(4) . . . . ? C18 C17 N2 C16 53.5(5) . . . . ? C22 C17 N2 Ru1 55.2(4) . . . . ? C18 C17 N2 Ru1 -122.6(3) . . . . ? C21 C20 N3 O2 -9.7(6) . . . . ? C19 C20 N3 O2 169.2(4) . . . . ? C21 C20 N3 O3 167.7(4) . . . . ? C19 C20 N3 O3 -13.4(5) . . . . ? C11 N1 Ru1 N2 175.9(3) . . . . ? C15 N1 Ru1 N2 -2.0(2) . . . . ? C11 N1 Ru1 C5 -101.3(3) . . . . ? C15 N1 Ru1 C5 80.8(3) . . . . ? C11 N1 Ru1 C9 -36.1(3) . . . . ? C15 N1 Ru1 C9 146.0(3) . . . . ? C11 N1 Ru1 C4 -74.2(3) . . . . ? C15 N1 Ru1 C4 107.8(3) . . . . ? C11 N1 Ru1 C6 -102.0(5) . . . . ? C15 N1 Ru1 C6 80.1(5) . . . . ? C11 N1 Ru1 C8 -5.3(3) . . . . ? C15 N1 Ru1 C8 176.8(2) . . . . ? C11 N1 Ru1 C7 8.6(5) . . . . ? C15 N1 Ru1 C7 -169.4(3) . . . . ? C11 N1 Ru1 Cl1 87.7(3) . . . . ? C15 N1 Ru1 Cl1 -90.2(2) . . . . ? C16 N2 Ru1 N1 3.2(3) . . . . ? C17 N2 Ru1 N1 179.3(3) . . . . ? C16 N2 Ru1 C5 -121.8(3) . . . . ? C17 N2 Ru1 C5 54.3(3) . . . . ? C16 N2 Ru1 C9 -73.0(4) . . . . ? C17 N2 Ru1 C9 103.1(3) . . . . ? C16 N2 Ru1 C4 -88.4(3) . . . . ? C17 N2 Ru1 C4 87.6(3) . . . . ? C16 N2 Ru1 C6 -159.0(3) . . . . ? C17 N2 Ru1 C6 17.1(3) . . . . ? C16 N2 Ru1 C8 -171.8(5) . . . . ? C17 N2 Ru1 C8 4.3(7) . . . . ? C16 N2 Ru1 C7 175.7(2) . . . . ? C17 N2 Ru1 C7 -8.2(3) . . . . ? C16 N2 Ru1 Cl1 88.9(3) . . . . ? C17 N2 Ru1 Cl1 -95.0(3) . . . . ? C4 C5 Ru1 N1 47.8(3) . . . . ? C6 C5 Ru1 N1 -179.67(19) . . . . ? C4 C5 Ru1 N2 122.6(2) . . . . ? C6 C5 Ru1 N2 -104.9(2) . . . . ? C4 C5 Ru1 C9 -31.0(2) . . . . ? C6 C5 Ru1 C9 101.5(2) . . . . ? C6 C5 Ru1 C4 132.5(3) . . . . ? C4 C5 Ru1 C6 -132.5(3) . . . . ? C4 C5 Ru1 C8 -67.3(2) . . . . ? C6 C5 Ru1 C8 65.2(2) . . . . ? C4 C5 Ru1 C7 -104.5(2) . . . . ? C6 C5 Ru1 C7 28.0(2) . . . . ? C4 C5 Ru1 Cl1 -149.96(18) . . . . ? C6 C5 Ru1 Cl1 -17.5(3) . . . . ? C8 C9 Ru1 N1 130.2(2) . . . . ? C4 C9 Ru1 N1 -95.1(2) . . . . ? C8 C9 Ru1 N2 -158.6(2) . . . . ? C4 C9 Ru1 N2 -23.9(3) . . . . ? C8 C9 Ru1 C5 -104.0(2) . . . . ? C4 C9 Ru1 C5 30.7(2) . . . . ? C8 C9 Ru1 C4 -134.7(3) . . . . ? C8 C9 Ru1 C6 -66.1(2) . . . . ? C4 C9 Ru1 C6 68.6(2) . . . . ? C4 C9 Ru1 C8 134.7(3) . . . . ? C8 C9 Ru1 C7 -29.3(2) . . . . ? C4 C9 Ru1 C7 105.3(2) . . . . ? C8 C9 Ru1 Cl1 43.4(2) . . . . ? C4 C9 Ru1 Cl1 178.11(17) . . . . ? C5 C4 Ru1 N1 -142.0(2) . . . . ? C9 C4 Ru1 N1 88.5(2) . . . . ? C2 C4 Ru1 N1 -23.5(4) . . . . ? C5 C4 Ru1 N2 -64.1(2) . . . . ? C9 C4 Ru1 N2 166.3(2) . . . . ? C2 C4 Ru1 N2 54.4(4) . . . . ? C9 C4 Ru1 C5 -129.5(3) . . . . ? C2 C4 Ru1 C5 118.5(5) . . . . ? C5 C4 Ru1 C9 129.5(3) . . . . ? C2 C4 Ru1 C9 -112.0(4) . . . . ? C5 C4 Ru1 C6 29.3(2) . . . . ? C9 C4 Ru1 C6 -100.3(2) . . . . ? C2 C4 Ru1 C6 147.8(4) . . . . ? C5 C4 Ru1 C8 102.1(2) . . . . ? C9 C4 Ru1 C8 -27.4(2) . . . . ? C2 C4 Ru1 C8 -139.4(4) . . . . ? C5 C4 Ru1 C7 65.4(2) . . . . ? C9 C4 Ru1 C7 -64.2(2) . . . . ? C2 C4 Ru1 C7 -176.1(4) . . . . ? C5 C4 Ru1 Cl1 124.5(3) . . . . ? C9 C4 Ru1 Cl1 -5.1(5) . . . . ? C2 C4 Ru1 Cl1 -117.0(4) . . . . ? C7 C6 Ru1 N1 134.5(4) . . . . ? C5 C6 Ru1 N1 0.9(5) . . . . ? C7 C6 Ru1 N2 -147.1(2) . . . . ? C5 C6 Ru1 N2 79.3(2) . . . . ? C7 C6 Ru1 C5 133.6(3) . . . . ? C7 C6 Ru1 C9 66.5(2) . . . . ? C5 C6 Ru1 C9 -67.1(2) . . . . ? C7 C6 Ru1 C4 104.7(2) . . . . ? C5 C6 Ru1 C4 -29.0(2) . . . . ? C7 C6 Ru1 C8 29.8(2) . . . . ? C5 C6 Ru1 C8 -103.8(2) . . . . ? C5 C6 Ru1 C7 -133.6(3) . . . . ? C7 C6 Ru1 Cl1 -55.9(2) . . . . ? C5 C6 Ru1 Cl1 170.48(18) . . . . ? C9 C8 Ru1 N1 -58.2(2) . . . . ? C7 C8 Ru1 N1 169.65(19) . . . . ? C9 C8 Ru1 N2 116.4(6) . . . . ? C7 C8 Ru1 N2 -15.8(7) . . . . ? C9 C8 Ru1 C5 65.4(2) . . . . ? C7 C8 Ru1 C5 -66.8(2) . . . . ? C7 C8 Ru1 C9 -132.2(3) . . . . ? C9 C8 Ru1 C4 28.1(2) . . . . ? C7 C8 Ru1 C4 -104.1(2) . . . . ? C9 C8 Ru1 C6 102.8(2) . . . . ? C7 C8 Ru1 C6 -29.4(2) . . . . ? C9 C8 Ru1 C7 132.2(3) . . . . ? C9 C8 Ru1 Cl1 -145.1(2) . . . . ? C7 C8 Ru1 Cl1 82.7(2) . . . . ? C6 C7 Ru1 N1 -151.9(3) . . . . ? C8 C7 Ru1 N1 -20.6(4) . . . . ? C10 C7 Ru1 N1 92.7(4) . . . . ? C6 C7 Ru1 N2 44.2(3) . . . . ? C8 C7 Ru1 N2 175.48(19) . . . . ? C10 C7 Ru1 N2 -71.2(4) . . . . ? C6 C7 Ru1 C5 -28.7(2) . . . . ? C8 C7 Ru1 C5 102.6(2) . . . . ? C10 C7 Ru1 C5 -144.1(4) . . . . ? C6 C7 Ru1 C9 -102.4(2) . . . . ? C8 C7 Ru1 C9 28.9(2) . . . . ? C10 C7 Ru1 C9 142.2(4) . . . . ? C6 C7 Ru1 C4 -65.4(2) . . . . ? C8 C7 Ru1 C4 65.9(2) . . . . ? C10 C7 Ru1 C4 179.2(4) . . . . ? C8 C7 Ru1 C6 131.3(3) . . . . ? C10 C7 Ru1 C6 -115.4(5) . . . . ? C6 C7 Ru1 C8 -131.3(3) . . . . ? C10 C7 Ru1 C8 113.3(5) . . . . ? C6 C7 Ru1 Cl1 130.0(2) . . . . ? C8 C7 Ru1 Cl1 -98.7(2) . . . . ? C10 C7 Ru1 Cl1 14.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.536 _refine_diff_density_min -0.859 _refine_diff_density_rms 0.100 # Attachment 'compound3.CIF' data_kcrulig5 _database_code_depnum_ccdc_archive 'CCDC 752543' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 Cl N3 O3 Ru' _chemical_formula_weight 512.95 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.889(6) _cell_length_b 8.6993(17) _cell_length_c 15.960(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.24(3) _cell_angle_gamma 90.00 _cell_volume 4083.7(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 19707 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7492 _exptl_absorpt_correction_T_max 0.9128 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38. ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18405 _diffrn_reflns_av_R_equivalents 0.0856 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4009 _reflns_number_gt 3516 _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/[\s^2^(Fo^2^)+(0.0515P)^2^+4.8719P] 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 4009 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.096210(7) 0.77642(2) 0.185023(12) 0.01941(11) Uani 1 1 d . . . Cl1 Cl 0.02537(2) 0.89614(8) 0.12352(4) 0.02939(17) Uani 1 1 d . . . O1 O 0.10553(8) 0.6170(2) -0.05986(13) 0.0333(5) Uani 1 1 d . . . N1 N 0.06484(8) 0.5757(3) 0.13422(14) 0.0239(5) Uani 1 1 d . . . C1 C 0.22636(12) 0.5478(4) 0.3357(3) 0.0506(10) Uani 1 1 d . . . H1A H 0.2143 0.5338 0.3884 0.076 Uiso 1 1 calc R . . H1B H 0.2425 0.6462 0.3377 0.076 Uiso 1 1 calc R . . H1C H 0.2474 0.4639 0.3296 0.076 Uiso 1 1 calc R . . O2 O 0.24057(9) 0.8167(3) -0.10442(18) 0.0498(6) Uani 1 1 d . . . N2 N 0.11140(8) 0.7698(3) 0.06114(15) 0.0231(5) Uani 1 1 d . . . C2 C 0.18706(10) 0.5469(3) 0.2596(2) 0.0303(6) Uani 1 1 d . . . H2 H 0.2002 0.5643 0.2070 0.036 Uiso 1 1 calc R . . O3 O 0.26356(10) 1.0498(3) -0.0829(2) 0.0675(9) Uani 1 1 d . . . N3 N 0.23643(9) 0.9465(3) -0.07704(17) 0.0363(6) Uani 1 1 d . . . C3 C 0.16343(11) 0.3914(4) 0.2509(2) 0.0376(7) Uani 1 1 d . . . H3A H 0.1508 0.3702 0.3024 0.056 Uiso 1 1 calc R . . H3B H 0.1854 0.3112 0.2436 0.056 Uiso 1 1 calc R . . H3C H 0.1389 0.3925 0.2013 0.056 Uiso 1 1 calc R . . C4 C 0.15639(9) 0.6808(3) 0.26916(17) 0.0227(5) Uani 1 1 d . . . C5 C 0.11760(9) 0.6709(3) 0.30979(16) 0.0227(5) Uani 1 1 d . . . H5 H 0.1095 0.5740 0.3301 0.027 Uiso 1 1 calc R . . C6 C 0.09083(10) 0.8014(3) 0.32069(17) 0.0240(6) Uani 1 1 d . . . H6 H 0.0651 0.7910 0.3477 0.029 Uiso 1 1 calc R . . C7 C 0.10236(9) 0.9473(3) 0.29132(17) 0.0245(6) Uani 1 1 d . . . C8 C 0.14045(9) 0.9598(3) 0.25011(17) 0.0267(6) Uani 1 1 d . . . H8 H 0.1487 1.0572 0.2306 0.032 Uiso 1 1 calc R . . C9 C 0.16629(9) 0.8286(3) 0.23788(17) 0.0258(6) Uani 1 1 d . . . H9 H 0.1909 0.8388 0.2080 0.031 Uiso 1 1 calc R . . C10 C 0.07344(11) 1.0847(3) 0.3002(2) 0.0337(7) Uani 1 1 d . . . H10A H 0.0421 1.0516 0.3003 0.051 Uiso 1 1 calc R . . H10B H 0.0740 1.1549 0.2524 0.051 Uiso 1 1 calc R . . H10C H 0.0852 1.1376 0.3538 0.051 Uiso 1 1 calc R . . C11 C 0.13667(9) 0.8881(3) 0.03026(17) 0.0241(6) Uani 1 1 d . . . C12 C 0.12638(10) 1.0406(3) 0.04516(18) 0.0269(6) Uani 1 1 d . . . H12 H 0.1011 1.0629 0.0717 0.032 Uiso 1 1 calc R . . C13 C 0.15231(10) 1.1611(3) 0.02198(18) 0.0295(6) Uani 1 1 d . . . H13 H 0.1448 1.2642 0.0333 0.035 Uiso 1 1 calc R . . C14 C 0.18901(10) 1.1309(3) -0.01742(18) 0.0296(6) Uani 1 1 d . . . H14 H 0.2074 1.2117 -0.0325 0.036 Uiso 1 1 calc R . . C15 C 0.19792(9) 0.9794(3) -0.03401(17) 0.0274(6) Uani 1 1 d . . . C16 C 0.17283(9) 0.8563(3) -0.01193(17) 0.0256(6) Uani 1 1 d . . . H16 H 0.1800 0.7537 -0.0251 0.031 Uiso 1 1 calc R . . C17 C 0.09845(9) 0.6454(3) 0.01284(17) 0.0242(6) Uani 1 1 d . . . C18 C 0.07105(9) 0.5352(3) 0.05590(17) 0.0230(6) Uani 1 1 d . . . C19 C 0.05238(10) 0.4031(3) 0.01685(18) 0.0274(6) Uani 1 1 d . . . H19 H 0.0577 0.3766 -0.0383 0.033 Uiso 1 1 calc R . . C20 C 0.02598(11) 0.3093(3) 0.05812(19) 0.0304(6) Uani 1 1 d . . . H20 H 0.0133 0.2168 0.0325 0.036 Uiso 1 1 calc R . . C21 C 0.01851(10) 0.3537(3) 0.13783(19) 0.0305(6) Uani 1 1 d . . . H21 H -0.0003 0.2934 0.1672 0.037 Uiso 1 1 calc R . . C22 C 0.03852(10) 0.4857(3) 0.17412(19) 0.0289(6) Uani 1 1 d . . . H22 H 0.0336 0.5145 0.2292 0.035 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 0.02221(15) 0.01964(16) 0.01628(15) -0.00032(7) 0.00315(10) -0.00251(8) Cl1 0.0256(3) 0.0337(4) 0.0267(4) -0.0038(3) -0.0013(3) 0.0031(3) O1 0.0471(13) 0.0320(11) 0.0227(11) -0.0057(8) 0.0117(9) -0.0055(10) N1 0.0280(12) 0.0227(12) 0.0206(12) 0.0006(9) 0.0028(9) -0.0019(9) C1 0.0311(17) 0.039(2) 0.075(3) -0.0151(18) -0.0096(17) 0.0129(15) O2 0.0490(15) 0.0464(15) 0.0613(17) -0.0111(13) 0.0299(13) -0.0053(12) N2 0.0255(13) 0.0244(12) 0.0201(12) 0.0009(9) 0.0057(10) -0.0003(9) C2 0.0299(15) 0.0281(16) 0.0342(17) -0.0037(12) 0.0090(13) 0.0043(12) O3 0.0600(18) 0.0609(18) 0.095(2) -0.0273(16) 0.0507(17) -0.0308(15) N3 0.0363(14) 0.0417(16) 0.0329(15) -0.0089(12) 0.0119(12) -0.0081(12) C3 0.0379(17) 0.0289(17) 0.0441(19) -0.0069(14) 0.0022(15) 0.0051(14) C4 0.0237(13) 0.0259(14) 0.0174(13) -0.0022(11) 0.0010(11) 0.0009(11) C5 0.0293(14) 0.0229(14) 0.0149(12) 0.0022(10) 0.0017(11) -0.0009(12) C6 0.0252(14) 0.0324(16) 0.0139(13) -0.0033(10) 0.0020(11) 0.0019(11) C7 0.0290(14) 0.0215(14) 0.0196(14) -0.0060(10) -0.0050(11) 0.0012(11) C8 0.0290(14) 0.0235(15) 0.0245(15) -0.0001(11) -0.0036(12) -0.0081(11) C9 0.0238(13) 0.0303(15) 0.0228(14) 0.0007(12) 0.0027(11) -0.0051(12) C10 0.0390(17) 0.0268(15) 0.0326(17) -0.0068(12) -0.0012(13) 0.0053(13) C11 0.0256(13) 0.0295(15) 0.0164(13) 0.0029(11) 0.0019(10) -0.0024(11) C12 0.0307(14) 0.0287(15) 0.0216(14) 0.0023(11) 0.0050(11) -0.0007(12) C13 0.0355(16) 0.0256(16) 0.0263(15) 0.0023(12) 0.0030(12) -0.0009(12) C14 0.0336(15) 0.0293(16) 0.0248(15) 0.0031(11) 0.0021(12) -0.0081(12) C15 0.0243(14) 0.0399(17) 0.0177(13) -0.0002(12) 0.0025(11) -0.0046(12) C16 0.0280(14) 0.0286(15) 0.0196(13) 0.0007(11) 0.0022(11) 0.0005(12) C17 0.0280(14) 0.0231(14) 0.0214(14) 0.0014(11) 0.0042(11) 0.0015(11) C18 0.0261(13) 0.0211(14) 0.0210(14) 0.0012(10) 0.0016(11) 0.0034(11) C19 0.0328(15) 0.0228(15) 0.0243(15) -0.0024(11) -0.0010(12) 0.0030(12) C20 0.0349(16) 0.0207(13) 0.0307(16) -0.0006(12) -0.0072(13) -0.0025(12) C21 0.0319(15) 0.0290(16) 0.0286(16) 0.0053(12) 0.0002(12) -0.0091(12) C22 0.0332(15) 0.0282(15) 0.0252(15) 0.0005(12) 0.0049(12) -0.0059(12) _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 2.077(2) . ? Ru1 N2 2.107(2) . ? Ru1 C9 2.163(3) . ? Ru1 C5 2.183(3) . ? Ru1 C4 2.207(3) . ? Ru1 C8 2.210(3) . ? Ru1 C6 2.210(3) . ? Ru1 C7 2.239(3) . ? Ru1 Cl1 2.4067(9) . ? O1 C17 1.241(3) . ? N1 C18 1.343(3) . ? N1 C22 1.347(4) . ? C1 C2 1.532(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 N3 1.225(3) . ? N2 C17 1.345(4) . ? N2 C11 1.416(3) . ? C2 C4 1.507(4) . ? C2 C3 1.521(4) . ? C2 H2 1.0000 . ? O3 N3 1.225(4) . ? N3 C15 1.470(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.428(4) . ? C4 C9 1.429(4) . ? C5 C6 1.418(4) . ? C5 H5 0.9500 . ? C6 C7 1.417(4) . ? C6 H6 0.9500 . ? C7 C8 1.417(4) . ? C7 C10 1.497(4) . ? C8 C9 1.411(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.392(4) . ? C11 C16 1.399(4) . ? C12 C13 1.392(4) . ? C12 H12 0.9500 . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 C15 1.380(4) . ? C14 H14 0.9500 . ? C15 C16 1.388(4) . ? C16 H16 0.9500 . ? C17 C18 1.504(4) . ? C18 C19 1.377(4) . ? C19 C20 1.381(4) . ? C19 H19 0.9500 . ? C20 C21 1.385(4) . ? C20 H20 0.9500 . ? C21 C22 1.375(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 N2 76.59(9) . . ? N1 Ru1 C9 131.86(10) . . ? N2 Ru1 C9 90.94(10) . . ? N1 Ru1 C5 92.37(10) . . ? N2 Ru1 C5 140.14(10) . . ? C9 Ru1 C5 68.05(11) . . ? N1 Ru1 C4 100.56(10) . . ? N2 Ru1 C4 105.80(10) . . ? C9 Ru1 C4 38.16(11) . . ? C5 Ru1 C4 37.97(10) . . ? N1 Ru1 C8 168.83(10) . . ? N2 Ru1 C8 104.49(10) . . ? C9 Ru1 C8 37.63(11) . . ? C5 Ru1 C8 79.69(11) . . ? C4 Ru1 C8 68.36(10) . . ? N1 Ru1 C6 111.02(10) . . ? N2 Ru1 C6 170.94(10) . . ? C9 Ru1 C6 80.29(11) . . ? C5 Ru1 C6 37.64(11) . . ? C4 Ru1 C6 68.56(10) . . ? C8 Ru1 C6 67.06(11) . . ? N1 Ru1 C7 145.55(10) . . ? N2 Ru1 C7 136.65(10) . . ? C9 Ru1 C7 67.77(11) . . ? C5 Ru1 C7 67.46(10) . . ? C4 Ru1 C7 80.85(10) . . ? C8 Ru1 C7 37.13(10) . . ? C6 Ru1 C7 37.13(10) . . ? N1 Ru1 Cl1 84.33(7) . . ? N2 Ru1 Cl1 87.13(7) . . ? C9 Ru1 Cl1 142.10(8) . . ? C5 Ru1 Cl1 130.38(8) . . ? C4 Ru1 Cl1 166.89(7) . . ? C8 Ru1 Cl1 106.79(8) . . ? C6 Ru1 Cl1 98.34(8) . . ? C7 Ru1 Cl1 88.25(8) . . ? C18 N1 C22 118.5(2) . . ? C18 N1 Ru1 117.15(18) . . ? C22 N1 Ru1 124.39(19) . . ? 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 . . ? C17 N2 C11 120.2(2) . . ? C17 N2 Ru1 118.17(18) . . ? C11 N2 Ru1 121.59(18) . . ? C4 C2 C3 114.6(2) . . ? C4 C2 C1 108.1(2) . . ? C3 C2 C1 110.8(3) . . ? C4 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? O2 N3 O3 122.6(3) . . ? O2 N3 C15 118.9(3) . . ? O3 N3 C15 118.5(3) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C9 116.6(2) . . ? C5 C4 C2 123.8(3) . . ? C9 C4 C2 119.5(2) . . ? C5 C4 Ru1 70.09(15) . . ? C9 C4 Ru1 69.23(15) . . ? C2 C4 Ru1 132.4(2) . . ? C6 C5 C4 121.9(3) . . ? C6 C5 Ru1 72.24(16) . . ? C4 C5 Ru1 71.95(15) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? Ru1 C5 H5 129.3 . . ? C7 C6 C5 120.1(3) . . ? C7 C6 Ru1 72.52(15) . . ? C5 C6 Ru1 70.12(15) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? Ru1 C6 H6 129.9 . . ? C8 C7 C6 119.0(2) . . ? C8 C7 C10 120.6(3) . . ? C6 C7 C10 120.4(3) . . ? C8 C7 Ru1 70.34(15) . . ? C6 C7 Ru1 70.34(15) . . ? C10 C7 Ru1 129.1(2) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 Ru1 69.36(16) . . ? C7 C8 Ru1 72.53(15) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? Ru1 C8 H8 131.1 . . ? C8 C9 C4 121.8(2) . . ? C8 C9 Ru1 73.01(16) . . ? C4 C9 Ru1 72.61(15) . . ? C8 C9 H9 119.1 . . ? C4 C9 H9 119.1 . . ? Ru1 C9 H9 127.4 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 118.9(3) . . ? C12 C11 N2 119.1(2) . . ? C16 C11 N2 122.0(3) . . ? C11 C12 C13 121.5(3) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 117.7(3) . . ? C15 C14 H14 121.2 . . ? C13 C14 H14 121.2 . . ? C14 C15 C16 123.9(3) . . ? C14 C15 N3 118.0(3) . . ? C16 C15 N3 118.1(3) . . ? C15 C16 C11 117.9(3) . . ? C15 C16 H16 121.0 . . ? C11 C16 H16 121.0 . . ? O1 C17 N2 128.1(3) . . ? O1 C17 C18 119.9(2) . . ? N2 C17 C18 112.0(2) . . ? N1 C18 C19 121.9(3) . . ? N1 C18 C17 115.8(2) . . ? C19 C18 C17 122.3(2) . . ? C18 C19 C20 119.8(3) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C21 118.2(3) . . ? C19 C20 H20 120.9 . . ? C21 C20 H20 120.9 . . ? C22 C21 C20 119.4(3) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? N1 C22 C21 122.2(3) . . ? N1 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? 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 N2 Ru1 N1 C18 3.94(19) . . . . ? C9 Ru1 N1 C18 -75.1(2) . . . . ? C5 Ru1 N1 C18 -137.3(2) . . . . ? C4 Ru1 N1 C18 -100.0(2) . . . . ? C8 Ru1 N1 C18 -93.0(5) . . . . ? C6 Ru1 N1 C18 -170.90(19) . . . . ? C7 Ru1 N1 C18 170.86(19) . . . . ? Cl1 Ru1 N1 C18 92.3(2) . . . . ? N2 Ru1 N1 C22 -175.2(3) . . . . ? C9 Ru1 N1 C22 105.8(2) . . . . ? C5 Ru1 N1 C22 43.5(2) . . . . ? C4 Ru1 N1 C22 80.9(2) . . . . ? C8 Ru1 N1 C22 87.8(5) . . . . ? C6 Ru1 N1 C22 9.9(3) . . . . ? C7 Ru1 N1 C22 -8.3(3) . . . . ? Cl1 Ru1 N1 C22 -86.8(2) . . . . ? N1 Ru1 N2 C17 -4.9(2) . . . . ? C9 Ru1 N2 C17 128.2(2) . . . . ? C5 Ru1 N2 C17 72.5(3) . . . . ? C4 Ru1 N2 C17 92.5(2) . . . . ? C8 Ru1 N2 C17 163.7(2) . . . . ? C7 Ru1 N2 C17 -174.10(19) . . . . ? Cl1 Ru1 N2 C17 -89.7(2) . . . . ? N1 Ru1 N2 C11 178.5(2) . . . . ? C9 Ru1 N2 C11 -48.4(2) . . . . ? C5 Ru1 N2 C11 -104.1(2) . . . . ? C4 Ru1 N2 C11 -84.1(2) . . . . ? C8 Ru1 N2 C11 -12.9(2) . . . . ? C7 Ru1 N2 C11 9.3(3) . . . . ? Cl1 Ru1 N2 C11 93.7(2) . . . . ? C3 C2 C4 C5 31.3(4) . . . . ? C1 C2 C4 C5 -92.7(3) . . . . ? C3 C2 C4 C9 -150.0(3) . . . . ? C1 C2 C4 C9 86.0(3) . . . . ? C3 C2 C4 Ru1 -62.0(4) . . . . ? C1 C2 C4 Ru1 174.0(2) . . . . ? N1 Ru1 C4 C5 -80.17(16) . . . . ? N2 Ru1 C4 C5 -159.08(16) . . . . ? C9 Ru1 C4 C5 130.3(2) . . . . ? C8 Ru1 C4 C5 101.28(18) . . . . ? C6 Ru1 C4 C5 28.41(16) . . . . ? C7 Ru1 C4 C5 64.87(17) . . . . ? Cl1 Ru1 C4 C5 30.8(4) . . . . ? N1 Ru1 C4 C9 149.49(16) . . . . ? N2 Ru1 C4 C9 70.58(17) . . . . ? C5 Ru1 C4 C9 -130.3(2) . . . . ? C8 Ru1 C4 C9 -29.06(16) . . . . ? C6 Ru1 C4 C9 -101.93(18) . . . . ? C7 Ru1 C4 C9 -65.47(16) . . . . ? Cl1 Ru1 C4 C9 -99.6(3) . . . . ? N1 Ru1 C4 C2 37.9(3) . . . . ? N2 Ru1 C4 C2 -41.0(3) . . . . ? C9 Ru1 C4 C2 -111.6(3) . . . . ? C5 Ru1 C4 C2 118.1(3) . . . . ? C8 Ru1 C4 C2 -140.6(3) . . . . ? C6 Ru1 C4 C2 146.5(3) . . . . ? C7 Ru1 C4 C2 -177.0(3) . . . . ? Cl1 Ru1 C4 C2 148.9(2) . . . . ? C9 C4 C5 C6 -1.6(4) . . . . ? C2 C4 C5 C6 177.2(3) . . . . ? Ru1 C4 C5 C6 -54.5(2) . . . . ? C9 C4 C5 Ru1 52.9(2) . . . . ? C2 C4 C5 Ru1 -128.3(3) . . . . ? N1 Ru1 C5 C6 -122.29(17) . . . . ? N2 Ru1 C5 C6 165.93(16) . . . . ? C9 Ru1 C5 C6 103.00(19) . . . . ? C4 Ru1 C5 C6 133.5(2) . . . . ? C8 Ru1 C5 C6 65.62(17) . . . . ? C7 Ru1 C5 C6 28.93(16) . . . . ? Cl1 Ru1 C5 C6 -37.7(2) . . . . ? N1 Ru1 C5 C4 104.20(16) . . . . ? N2 Ru1 C5 C4 32.4(2) . . . . ? C9 Ru1 C5 C4 -30.51(16) . . . . ? C8 Ru1 C5 C4 -67.90(17) . . . . ? C6 Ru1 C5 C4 -133.5(2) . . . . ? C7 Ru1 C5 C4 -104.59(18) . . . . ? Cl1 Ru1 C5 C4 -171.24(12) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? Ru1 C5 C6 C7 -54.7(2) . . . . ? C4 C5 C6 Ru1 54.3(2) . . . . ? N1 Ru1 C6 C7 -162.93(15) . . . . ? C9 Ru1 C6 C7 65.80(17) . . . . ? C5 Ru1 C6 C7 132.3(2) . . . . ? C4 Ru1 C6 C7 103.62(18) . . . . ? C8 Ru1 C6 C7 28.93(16) . . . . ? Cl1 Ru1 C6 C7 -75.84(16) . . . . ? N1 Ru1 C6 C5 64.80(18) . . . . ? C9 Ru1 C6 C5 -66.47(17) . . . . ? C4 Ru1 C6 C5 -28.64(16) . . . . ? C8 Ru1 C6 C5 -103.33(18) . . . . ? C7 Ru1 C6 C5 -132.3(2) . . . . ? Cl1 Ru1 C6 C5 151.90(15) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? Ru1 C6 C7 C8 -52.6(2) . . . . ? C5 C6 C7 C10 178.1(3) . . . . ? Ru1 C6 C7 C10 124.6(3) . . . . ? C5 C6 C7 Ru1 53.5(2) . . . . ? N1 Ru1 C7 C8 161.40(17) . . . . ? N2 Ru1 C7 C8 -37.3(2) . . . . ? C9 Ru1 C7 C8 28.66(16) . . . . ? C5 Ru1 C7 C8 103.13(18) . . . . ? C4 Ru1 C7 C8 66.04(17) . . . . ? C6 Ru1 C7 C8 132.4(2) . . . . ? Cl1 Ru1 C7 C8 -121.27(16) . . . . ? N1 Ru1 C7 C6 29.0(3) . . . . ? N2 Ru1 C7 C6 -169.75(15) . . . . ? C9 Ru1 C7 C6 -103.77(18) . . . . ? C5 Ru1 C7 C6 -29.30(17) . . . . ? C4 Ru1 C7 C6 -66.39(17) . . . . ? C8 Ru1 C7 C6 -132.4(2) . . . . ? Cl1 Ru1 C7 C6 106.30(16) . . . . ? N1 Ru1 C7 C10 -84.7(3) . . . . ? N2 Ru1 C7 C10 76.6(3) . . . . ? C9 Ru1 C7 C10 142.6(3) . . . . ? C5 Ru1 C7 C10 -143.0(3) . . . . ? C4 Ru1 C7 C10 180.0(3) . . . . ? C8 Ru1 C7 C10 113.9(3) . . . . ? C6 Ru1 C7 C10 -113.7(3) . . . . ? Cl1 Ru1 C7 C10 -7.4(3) . . . . ? C6 C7 C8 C9 0.5(4) . . . . ? C10 C7 C8 C9 -176.7(3) . . . . ? Ru1 C7 C8 C9 -52.1(2) . . . . ? C6 C7 C8 Ru1 52.6(2) . . . . ? C10 C7 C8 Ru1 -124.6(3) . . . . ? N1 Ru1 C8 C9 22.1(6) . . . . ? N2 Ru1 C8 C9 -72.10(17) . . . . ? C5 Ru1 C8 C9 67.27(17) . . . . ? C4 Ru1 C8 C9 29.44(16) . . . . ? C6 Ru1 C8 C9 104.43(18) . . . . ? C7 Ru1 C8 C9 133.4(2) . . . . ? Cl1 Ru1 C8 C9 -163.47(14) . . . . ? N1 Ru1 C8 C7 -111.3(5) . . . . ? N2 Ru1 C8 C7 154.54(16) . . . . ? C9 Ru1 C8 C7 -133.4(2) . . . . ? C5 Ru1 C8 C7 -66.09(17) . . . . ? C4 Ru1 C8 C7 -103.92(18) . . . . ? C6 Ru1 C8 C7 -28.93(16) . . . . ? Cl1 Ru1 C8 C7 63.17(16) . . . . ? C7 C8 C9 C4 -2.6(4) . . . . ? Ru1 C8 C9 C4 -56.1(2) . . . . ? C7 C8 C9 Ru1 53.6(2) . . . . ? C5 C4 C9 C8 3.0(4) . . . . ? C2 C4 C9 C8 -175.8(3) . . . . ? Ru1 C4 C9 C8 56.3(2) . . . . ? C5 C4 C9 Ru1 -53.3(2) . . . . ? C2 C4 C9 Ru1 127.9(2) . . . . ? N1 Ru1 C9 C8 -174.39(15) . . . . ? N2 Ru1 C9 C8 112.87(16) . . . . ? C5 Ru1 C9 C8 -101.94(18) . . . . ? C4 Ru1 C9 C8 -132.3(2) . . . . ? C6 Ru1 C9 C8 -64.80(17) . . . . ? C7 Ru1 C9 C8 -28.30(16) . . . . ? Cl1 Ru1 C9 C8 26.3(2) . . . . ? N1 Ru1 C9 C4 -42.1(2) . . . . ? N2 Ru1 C9 C4 -114.83(16) . . . . ? C5 Ru1 C9 C4 30.37(15) . . . . ? C8 Ru1 C9 C4 132.3(2) . . . . ? C6 Ru1 C9 C4 67.51(16) . . . . ? C7 Ru1 C9 C4 104.01(17) . . . . ? Cl1 Ru1 C9 C4 158.64(12) . . . . ? C17 N2 C11 C12 139.1(3) . . . . ? Ru1 N2 C11 C12 -44.4(3) . . . . ? C17 N2 C11 C16 -43.4(4) . . . . ? Ru1 N2 C11 C16 133.1(2) . . . . ? C16 C11 C12 C13 -2.5(4) . . . . ? N2 C11 C12 C13 175.1(3) . . . . ? C11 C12 C13 C14 0.5(4) . . . . ? C12 C13 C14 C15 1.4(4) . . . . ? C13 C14 C15 C16 -1.4(4) . . . . ? C13 C14 C15 N3 179.1(3) . . . . ? O2 N3 C15 C14 -168.5(3) . . . . ? O3 N3 C15 C14 12.6(4) . . . . ? O2 N3 C15 C16 12.0(4) . . . . ? O3 N3 C15 C16 -166.9(3) . . . . ? C14 C15 C16 C11 -0.6(4) . . . . ? N3 C15 C16 C11 179.0(2) . . . . ? C12 C11 C16 C15 2.5(4) . . . . ? N2 C11 C16 C15 -175.0(3) . . . . ? C11 N2 C17 O1 -0.5(5) . . . . ? Ru1 N2 C17 O1 -177.2(2) . . . . ? C11 N2 C17 C18 -178.6(2) . . . . ? Ru1 N2 C17 C18 4.8(3) . . . . ? C22 N1 C18 C19 -1.8(4) . . . . ? Ru1 N1 C18 C19 178.9(2) . . . . ? C22 N1 C18 C17 176.5(2) . . . . ? Ru1 N1 C18 C17 -2.7(3) . . . . ? O1 C17 C18 N1 -179.6(3) . . . . ? N2 C17 C18 N1 -1.3(4) . . . . ? O1 C17 C18 C19 -1.2(4) . . . . ? N2 C17 C18 C19 177.0(3) . . . . ? N1 C18 C19 C20 0.8(4) . . . . ? C17 C18 C19 C20 -177.4(3) . . . . ? C18 C19 C20 C21 1.1(4) . . . . ? C19 C20 C21 C22 -2.0(5) . . . . ? C18 N1 C22 C21 0.9(4) . . . . ? Ru1 N1 C22 C21 -179.9(2) . . . . ? C20 C21 C22 N1 1.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.842 _refine_diff_density_min -1.894 _refine_diff_density_rms 0.271 # Attachment 'compound4.CIF' data_kcrulig12 _database_code_depnum_ccdc_archive 'CCDC 752544' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 Cl N3 O3 Ru' _chemical_formula_sum 'C26 H24 Cl N3 O3 Ru' _chemical_formula_weight 563.00 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' 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 9.1990(2) _cell_length_b 18.2030(4) _cell_length_c 14.1460(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.5280(10) _cell_angle_gamma 90.00 _cell_volume 2312.34(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 46871 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.828 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 37107 _diffrn_reflns_av_R_equivalents 0.1143 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5286 _reflns_number_gt 4153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112--122)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112--122)' _computing_molecular_graphics 'ORTEP-III (Farrugia, 2001)' _computing_publication_material ; local program ; _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^)+(0.0675P)^2^+1.3679P] 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 5286 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.23194(3) 0.186086(13) 0.216975(18) 0.03112(11) Uani 1 1 d . . . Cl1 Cl 0.05060(9) 0.23179(4) 0.08056(6) 0.0388(2) Uani 1 1 d . . . N2 N 0.1890(3) 0.08333(13) 0.14732(19) 0.0326(6) Uani 1 1 d . . . C3 C 0.0701(4) 0.03631(17) 0.1495(2) 0.0333(7) Uani 1 1 d . . . C4 C -0.0523(4) 0.06037(19) 0.1839(2) 0.0385(7) Uani 1 1 d . . . H4 H -0.0548 0.1093 0.2070 0.046 Uiso 1 1 calc R . . C5 C -0.1698(4) 0.0137(2) 0.1849(3) 0.0447(8) Uani 1 1 d . . . H5 H -0.2524 0.0306 0.2091 0.054 Uiso 1 1 calc R . . N6 N 0.3809(3) 0.18465(13) 0.1246(2) 0.0343(6) Uani 1 1 d . . . C6 C -0.1688(4) -0.0585(2) 0.1504(3) 0.0451(8) Uani 1 1 d . . . H6 H -0.2488 -0.0907 0.1536 0.054 Uiso 1 1 calc R . . C7 C -0.0531(4) -0.08253(18) 0.1123(2) 0.0412(8) Uani 1 1 d . . . H7 H -0.0555 -0.1309 0.0867 0.049 Uiso 1 1 calc R . . C8 C 0.0705(4) -0.03643(17) 0.1103(2) 0.0359(7) Uani 1 1 d . . . C9 C 0.1893(4) -0.05753(18) 0.0683(2) 0.0389(7) Uani 1 1 d . . . H9 H 0.1929 -0.1060 0.0441 0.047 Uiso 1 1 calc R . . C10 C 0.2984(4) -0.00917(17) 0.0622(2) 0.0387(7) Uani 1 1 d . . . H10 H 0.3777 -0.0229 0.0326 0.046 Uiso 1 1 calc R . . C11 C 0.2925(4) 0.06204(17) 0.1007(2) 0.0345(7) Uani 1 1 d . . . O12 O 0.4888(3) 0.10541(13) 0.0311(2) 0.0502(6) Uani 1 1 d . . . C12 C 0.4018(4) 0.11998(18) 0.0836(2) 0.0375(7) Uani 1 1 d . . . C14 C 0.4665(4) 0.24663(17) 0.1092(2) 0.0344(7) Uani 1 1 d . . . C15 C 0.4017(4) 0.31608(16) 0.1078(3) 0.0366(7) Uani 1 1 d . . . H15 H 0.3007 0.3212 0.1126 0.044 Uiso 1 1 calc R . . N16 N 0.4163(4) 0.45024(16) 0.1015(2) 0.0494(8) Uani 1 1 d . . . C16 C 0.4867(4) 0.37721(18) 0.0996(2) 0.0392(7) Uani 1 1 d . . . C17 C 0.6319(4) 0.37481(19) 0.0895(2) 0.0420(8) Uani 1 1 d . . . H17 H 0.6864 0.4182 0.0834 0.050 Uiso 1 1 calc R . . C18 C 0.6944(4) 0.30569(19) 0.0886(3) 0.0417(8) Uani 1 1 d . . . H18 H 0.7942 0.3015 0.0812 0.050 Uiso 1 1 calc R . . C19 C 0.6151(4) 0.24240(19) 0.0984(2) 0.0372(7) Uani 1 1 d . . . H19 H 0.6613 0.1958 0.0978 0.045 Uiso 1 1 calc R . . C20 C 0.3965(4) 0.1662(2) 0.3543(3) 0.0411(8) Uani 1 1 d . . . C21 C 0.2556(4) 0.1373(2) 0.3603(2) 0.0418(8) Uani 1 1 d . . . H21 H 0.2474 0.0866 0.3740 0.050 Uiso 1 1 calc R . . C22 C 0.1267(4) 0.18212(19) 0.3463(3) 0.0419(8) Uani 1 1 d . . . H22 H 0.0355 0.1619 0.3555 0.050 Uiso 1 1 calc R . . C23 C 0.1324(4) 0.2558(2) 0.3192(2) 0.0423(8) Uani 1 1 d . . . C24 C 0.2714(4) 0.28458(19) 0.3071(3) 0.0391(7) Uani 1 1 d . . . H24 H 0.2774 0.3339 0.2863 0.047 Uiso 1 1 calc R . . C25 C 0.3995(4) 0.24014(18) 0.3259(2) 0.0372(7) Uani 1 1 d . . . H25 H 0.4915 0.2608 0.3191 0.045 Uiso 1 1 calc R . . C26 C 0.5369(4) 0.1189(2) 0.3806(3) 0.0553(10) Uani 1 1 d . . . H26 H 0.5578 0.1137 0.4527 0.066 Uiso 1 1 calc R . . C27 C 0.6745(4) 0.1554(3) 0.3584(3) 0.0646(11) Uani 1 1 d . . . H27A H 0.7611 0.1235 0.3799 0.097 Uiso 1 1 calc R . . H27B H 0.6916 0.2026 0.3926 0.097 Uiso 1 1 calc R . . H27C H 0.6593 0.1638 0.2885 0.097 Uiso 1 1 calc R . . C28 C 0.5196(6) 0.0432(3) 0.3424(4) 0.0793(15) Uani 1 1 d . . . H28A H 0.4362 0.0193 0.3631 0.119 Uiso 1 1 calc R . . H28B H 0.6113 0.0155 0.3672 0.119 Uiso 1 1 calc R . . H28C H 0.4999 0.0445 0.2715 0.119 Uiso 1 1 calc R . . C29 C -0.0041(5) 0.3032(2) 0.3011(3) 0.0595(12) Uani 1 1 d . . . H29A H -0.0928 0.2724 0.2813 0.089 Uiso 1 1 calc R . . H29B H 0.0008 0.3386 0.2496 0.089 Uiso 1 1 calc R . . H29C H -0.0095 0.3298 0.3605 0.089 Uiso 1 1 calc R . . O16A O 0.4898(3) 0.50531(13) 0.09831(19) 0.0532(7) Uani 1 1 d . . . O16B O 0.2864(4) 0.45187(17) 0.1072(4) 0.1151(18) 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 Ru1 0.03027(16) 0.02820(16) 0.03608(17) -0.00563(10) 0.00983(11) 0.00167(9) Cl1 0.0359(4) 0.0378(4) 0.0420(5) -0.0035(3) 0.0069(3) 0.0071(3) N2 0.0356(14) 0.0299(13) 0.0331(14) -0.0015(10) 0.0090(11) 0.0034(11) C3 0.0400(17) 0.0288(15) 0.0297(16) -0.0021(12) 0.0045(13) 0.0015(13) C4 0.0406(18) 0.0382(18) 0.0370(17) -0.0056(15) 0.0095(14) -0.0025(14) C5 0.0421(19) 0.052(2) 0.0404(19) -0.0054(16) 0.0098(15) -0.0048(16) N6 0.0328(14) 0.0302(14) 0.0423(16) -0.0022(11) 0.0133(12) 0.0047(10) C6 0.045(2) 0.044(2) 0.045(2) 0.0038(16) 0.0063(16) -0.0093(16) C7 0.050(2) 0.0322(17) 0.0376(18) 0.0020(14) 0.0014(15) -0.0039(14) C8 0.0479(19) 0.0288(15) 0.0294(16) 0.0023(12) 0.0049(14) 0.0020(14) C9 0.055(2) 0.0263(15) 0.0338(17) -0.0004(13) 0.0065(14) 0.0100(14) C10 0.050(2) 0.0308(16) 0.0376(18) -0.0014(13) 0.0138(15) 0.0081(14) C11 0.0392(17) 0.0287(15) 0.0361(17) 0.0005(13) 0.0093(13) 0.0084(13) O12 0.0521(15) 0.0402(13) 0.0681(17) -0.0085(12) 0.0347(14) 0.0023(11) C12 0.0382(17) 0.0370(18) 0.0393(18) -0.0005(14) 0.0127(14) 0.0084(14) C14 0.0347(16) 0.0346(17) 0.0340(17) -0.0015(13) 0.0073(13) 0.0025(13) C15 0.0331(17) 0.0328(17) 0.0437(19) -0.0039(13) 0.0082(14) 0.0031(13) N16 0.0489(18) 0.0338(16) 0.063(2) -0.0043(14) 0.0070(15) 0.0022(14) C16 0.0419(18) 0.0366(17) 0.0389(18) -0.0003(14) 0.0084(14) 0.0004(14) C17 0.0442(19) 0.0407(19) 0.0407(19) 0.0014(15) 0.0080(15) -0.0071(15) C18 0.0321(17) 0.053(2) 0.0413(19) 0.0035(15) 0.0117(15) 0.0003(14) C19 0.0355(17) 0.0399(18) 0.0368(18) 0.0023(14) 0.0090(14) 0.0069(14) C20 0.0427(19) 0.0403(18) 0.0395(18) -0.0053(15) 0.0075(15) 0.0016(15) C21 0.053(2) 0.0389(18) 0.0367(18) -0.0045(14) 0.0165(15) -0.0050(15) C22 0.0381(18) 0.052(2) 0.0386(19) -0.0128(15) 0.0143(15) -0.0069(15) C23 0.0418(19) 0.047(2) 0.0377(18) -0.0156(15) 0.0072(15) 0.0080(15) C24 0.0444(19) 0.0304(16) 0.0426(18) -0.0088(14) 0.0097(15) 0.0022(14) C25 0.0371(17) 0.0369(17) 0.0375(18) -0.0077(14) 0.0076(14) -0.0071(14) C26 0.051(2) 0.058(2) 0.058(2) 0.0092(19) 0.0133(19) 0.0184(19) C27 0.044(2) 0.081(3) 0.069(3) 0.003(2) 0.013(2) 0.011(2) C28 0.064(3) 0.067(3) 0.108(4) 0.001(3) 0.020(3) 0.016(2) C29 0.050(2) 0.070(3) 0.058(3) -0.025(2) 0.010(2) 0.0212(19) O16A 0.0767(19) 0.0347(13) 0.0494(15) 0.0027(11) 0.0167(13) -0.0052(13) O16B 0.058(2) 0.0383(17) 0.254(6) -0.023(2) 0.046(3) 0.0055(15) _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 N6 2.089(3) . ? Ru1 N2 2.111(2) . ? Ru1 C25 2.165(3) . ? Ru1 C21 2.181(3) . ? Ru1 C24 2.184(3) . ? Ru1 C20 2.218(4) . ? Ru1 C22 2.249(4) . ? Ru1 C23 2.261(3) . ? Ru1 Cl1 2.4088(8) . ? N2 C11 1.329(4) . ? N2 C3 1.394(4) . ? C3 C4 1.391(5) . ? C3 C8 1.436(4) . ? C4 C5 1.377(5) . ? C4 H4 0.9500 . ? C5 C6 1.402(5) . ? C5 H5 0.9500 . ? N6 C12 1.345(4) . ? N6 C14 1.419(4) . ? C6 C7 1.366(5) . ? C6 H6 0.9500 . ? C7 C8 1.418(5) . ? C7 H7 0.9500 . ? C8 C9 1.405(5) . ? C9 C10 1.352(5) . ? C9 H9 0.9500 . ? C10 C11 1.411(4) . ? C10 H10 0.9500 . ? C11 C12 1.512(5) . ? O12 C12 1.233(4) . ? C14 C15 1.396(4) . ? C14 C19 1.410(4) . ? C15 C16 1.380(5) . ? C15 H15 0.9500 . ? N16 O16A 1.215(4) . ? N16 O16B 1.216(4) . ? N16 C16 1.481(4) . ? C16 C17 1.374(5) . ? C17 C18 1.384(5) . ? C17 H17 0.9500 . ? C18 C19 1.386(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C25 1.407(5) . ? C20 C21 1.418(5) . ? C20 C26 1.530(5) . ? C21 C22 1.417(5) . ? C21 H21 0.9500 . ? C22 C23 1.398(5) . ? C22 H22 0.9500 . ? C23 C24 1.426(5) . ? C23 C29 1.500(5) . ? C24 C25 1.407(5) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C28 1.476(6) . ? C26 C27 1.521(6) . ? C26 H26 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? 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 N6 Ru1 N2 77.23(10) . . ? N6 Ru1 C25 89.32(12) . . ? N2 Ru1 C25 140.10(11) . . ? N6 Ru1 C21 129.03(12) . . ? N2 Ru1 C21 92.52(11) . . ? C25 Ru1 C21 67.14(13) . . ? N6 Ru1 C24 109.09(12) . . ? N2 Ru1 C24 172.00(12) . . ? C25 Ru1 C24 37.74(12) . . ? C21 Ru1 C24 79.69(13) . . ? N6 Ru1 C20 97.47(12) . . ? N2 Ru1 C20 106.70(12) . . ? C25 Ru1 C20 37.42(13) . . ? C21 Ru1 C20 37.61(13) . . ? C24 Ru1 C20 68.12(13) . . ? N6 Ru1 C22 164.80(13) . . ? N2 Ru1 C22 106.33(11) . . ? C25 Ru1 C22 78.54(13) . . ? C21 Ru1 C22 37.27(13) . . ? C24 Ru1 C22 66.28(13) . . ? C20 Ru1 C22 67.33(13) . . ? N6 Ru1 C23 144.96(12) . . ? N2 Ru1 C23 137.28(12) . . ? C25 Ru1 C23 67.32(13) . . ? C21 Ru1 C23 66.80(13) . . ? C24 Ru1 C23 37.36(13) . . ? C20 Ru1 C23 79.93(13) . . ? C22 Ru1 C23 36.12(13) . . ? N6 Ru1 Cl1 86.43(8) . . ? N2 Ru1 Cl1 84.55(7) . . ? C25 Ru1 Cl1 132.49(9) . . ? C21 Ru1 Cl1 142.89(10) . . ? C24 Ru1 Cl1 100.52(9) . . ? C20 Ru1 Cl1 168.64(9) . . ? C22 Ru1 Cl1 108.50(10) . . ? C23 Ru1 Cl1 90.73(9) . . ? C11 N2 C3 118.8(3) . . ? C11 N2 Ru1 114.1(2) . . ? C3 N2 Ru1 127.0(2) . . ? C4 C3 N2 120.8(3) . . ? C4 C3 C8 119.7(3) . . ? N2 C3 C8 119.4(3) . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C12 N6 C14 119.6(3) . . ? C12 N6 Ru1 117.1(2) . . ? C14 N6 Ru1 123.2(2) . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 121.0(3) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 123.1(3) . . ? C9 C8 C3 118.8(3) . . ? C7 C8 C3 118.0(3) . . ? C10 C9 C8 120.3(3) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 118.8(3) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? N2 C11 C10 123.4(3) . . ? N2 C11 C12 116.7(3) . . ? C10 C11 C12 119.8(3) . . ? O12 C12 N6 128.3(3) . . ? O12 C12 C11 119.1(3) . . ? N6 C12 C11 112.3(3) . . ? C15 C14 C19 118.0(3) . . ? C15 C14 N6 118.2(3) . . ? C19 C14 N6 123.8(3) . . ? C16 C15 C14 118.9(3) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? O16A N16 O16B 123.0(3) . . ? O16A N16 C16 119.4(3) . . ? O16B N16 C16 117.6(3) . . ? C17 C16 C15 124.4(3) . . ? C17 C16 N16 117.9(3) . . ? C15 C16 N16 117.7(3) . . ? C16 C17 C18 116.4(3) . . ? C16 C17 H17 121.8 . . ? C18 C17 H17 121.8 . . ? C17 C18 C19 121.7(3) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C18 C19 C14 120.6(3) . . ? C18 C19 H19 119.7 . . ? C14 C19 H19 119.7 . . ? C25 C20 C21 116.6(3) . . ? C25 C20 C26 122.7(3) . . ? C21 C20 C26 120.7(3) . . ? C25 C20 Ru1 69.24(19) . . ? C21 C20 Ru1 69.8(2) . . ? C26 C20 Ru1 133.2(3) . . ? C22 C21 C20 121.7(3) . . ? C22 C21 Ru1 74.0(2) . . ? C20 C21 Ru1 72.6(2) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? Ru1 C21 H21 126.1 . . ? C23 C22 C21 120.7(3) . . ? C23 C22 Ru1 72.4(2) . . ? C21 C22 Ru1 68.7(2) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? Ru1 C22 H22 132.2 . . ? C22 C23 C24 118.3(3) . . ? C22 C23 C29 121.3(4) . . ? C24 C23 C29 120.4(4) . . ? C22 C23 Ru1 71.5(2) . . ? C24 C23 Ru1 68.38(18) . . ? C29 C23 Ru1 130.8(3) . . ? C25 C24 C23 120.1(3) . . ? C25 C24 Ru1 70.38(18) . . ? C23 C24 Ru1 74.26(19) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? Ru1 C24 H24 127.5 . . ? C24 C25 C20 122.4(3) . . ? C24 C25 Ru1 71.88(19) . . ? C20 C25 Ru1 73.35(19) . . ? C24 C25 H25 118.8 . . ? C20 C25 H25 118.8 . . ? Ru1 C25 H25 128.4 . . ? C28 C26 C27 111.2(4) . . ? C28 C26 C20 114.7(4) . . ? C27 C26 C20 113.6(3) . . ? C28 C26 H26 105.5 . . ? C27 C26 H26 105.5 . . ? C20 C26 H26 105.5 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C23 C29 H29A 109.5 . . ? C23 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C23 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N6 Ru1 N2 C11 14.4(2) . . . . ? C25 Ru1 N2 C11 -58.8(3) . . . . ? C21 Ru1 N2 C11 -115.2(2) . . . . ? C20 Ru1 N2 C11 -79.7(2) . . . . ? C22 Ru1 N2 C11 -150.4(2) . . . . ? C23 Ru1 N2 C11 -172.9(2) . . . . ? Cl1 Ru1 N2 C11 101.9(2) . . . . ? N6 Ru1 N2 C3 -168.6(3) . . . . ? C25 Ru1 N2 C3 118.2(3) . . . . ? C21 Ru1 N2 C3 61.8(3) . . . . ? C20 Ru1 N2 C3 97.3(3) . . . . ? C22 Ru1 N2 C3 26.6(3) . . . . ? C23 Ru1 N2 C3 4.1(3) . . . . ? Cl1 Ru1 N2 C3 -81.1(2) . . . . ? C11 N2 C3 C4 -169.9(3) . . . . ? Ru1 N2 C3 C4 13.2(4) . . . . ? C11 N2 C3 C8 6.4(4) . . . . ? Ru1 N2 C3 C8 -170.5(2) . . . . ? N2 C3 C4 C5 179.3(3) . . . . ? C8 C3 C4 C5 3.1(5) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? N2 Ru1 N6 C12 -12.8(2) . . . . ? C25 Ru1 N6 C12 129.3(3) . . . . ? C21 Ru1 N6 C12 70.0(3) . . . . ? C24 Ru1 N6 C12 162.1(2) . . . . ? C20 Ru1 N6 C12 92.7(3) . . . . ? C22 Ru1 N6 C12 92.6(5) . . . . ? C23 Ru1 N6 C12 175.8(2) . . . . ? Cl1 Ru1 N6 C12 -98.0(2) . . . . ? N2 Ru1 N6 C14 171.6(3) . . . . ? C25 Ru1 N6 C14 -46.3(3) . . . . ? C21 Ru1 N6 C14 -105.7(3) . . . . ? C24 Ru1 N6 C14 -13.6(3) . . . . ? C20 Ru1 N6 C14 -82.9(3) . . . . ? C22 Ru1 N6 C14 -83.1(5) . . . . ? C23 Ru1 N6 C14 0.2(4) . . . . ? Cl1 Ru1 N6 C14 86.3(2) . . . . ? C4 C5 C6 C7 -2.3(5) . . . . ? C5 C6 C7 C8 2.6(5) . . . . ? C6 C7 C8 C9 -177.3(3) . . . . ? C6 C7 C8 C3 -0.1(5) . . . . ? C4 C3 C8 C9 174.6(3) . . . . ? N2 C3 C8 C9 -1.7(4) . . . . ? C4 C3 C8 C7 -2.8(4) . . . . ? N2 C3 C8 C7 -179.1(3) . . . . ? C7 C8 C9 C10 175.1(3) . . . . ? C3 C8 C9 C10 -2.2(5) . . . . ? C8 C9 C10 C11 1.4(5) . . . . ? C3 N2 C11 C10 -7.5(5) . . . . ? Ru1 N2 C11 C10 169.8(2) . . . . ? C3 N2 C11 C12 168.5(3) . . . . ? Ru1 N2 C11 C12 -14.3(3) . . . . ? C9 C10 C11 N2 3.6(5) . . . . ? C9 C10 C11 C12 -172.2(3) . . . . ? C14 N6 C12 O12 -0.2(5) . . . . ? Ru1 N6 C12 O12 -176.1(3) . . . . ? C14 N6 C12 C11 -175.1(3) . . . . ? Ru1 N6 C12 C11 9.1(4) . . . . ? N2 C11 C12 O12 -171.7(3) . . . . ? C10 C11 C12 O12 4.5(5) . . . . ? N2 C11 C12 N6 3.7(4) . . . . ? C10 C11 C12 N6 179.8(3) . . . . ? C12 N6 C14 C15 148.6(3) . . . . ? Ru1 N6 C14 C15 -35.8(4) . . . . ? C12 N6 C14 C19 -33.7(5) . . . . ? Ru1 N6 C14 C19 141.8(3) . . . . ? C19 C14 C15 C16 -2.2(5) . . . . ? N6 C14 C15 C16 175.6(3) . . . . ? C14 C15 C16 C17 2.0(5) . . . . ? C14 C15 C16 N16 -178.1(3) . . . . ? O16A N16 C16 C17 -3.1(5) . . . . ? O16B N16 C16 C17 177.6(4) . . . . ? O16A N16 C16 C15 177.0(3) . . . . ? O16B N16 C16 C15 -2.2(6) . . . . ? C15 C16 C17 C18 -0.6(5) . . . . ? N16 C16 C17 C18 179.6(3) . . . . ? C16 C17 C18 C19 -0.6(5) . . . . ? C17 C18 C19 C14 0.3(5) . . . . ? C15 C14 C19 C18 1.2(5) . . . . ? N6 C14 C19 C18 -176.5(3) . . . . ? N6 Ru1 C20 C25 79.0(2) . . . . ? N2 Ru1 C20 C25 157.83(19) . . . . ? C21 Ru1 C20 C25 -130.5(3) . . . . ? C24 Ru1 C20 C25 -28.6(2) . . . . ? C22 Ru1 C20 C25 -101.1(2) . . . . ? C23 Ru1 C20 C25 -65.6(2) . . . . ? Cl1 Ru1 C20 C25 -30.5(6) . . . . ? N6 Ru1 C20 C21 -150.5(2) . . . . ? N2 Ru1 C20 C21 -71.7(2) . . . . ? C25 Ru1 C20 C21 130.5(3) . . . . ? C24 Ru1 C20 C21 101.9(2) . . . . ? C22 Ru1 C20 C21 29.4(2) . . . . ? C23 Ru1 C20 C21 64.8(2) . . . . ? Cl1 Ru1 C20 C21 100.0(5) . . . . ? N6 Ru1 C20 C26 -36.9(4) . . . . ? N2 Ru1 C20 C26 42.0(4) . . . . ? C25 Ru1 C20 C26 -115.9(4) . . . . ? C21 Ru1 C20 C26 113.7(4) . . . . ? C24 Ru1 C20 C26 -144.5(4) . . . . ? C22 Ru1 C20 C26 143.1(4) . . . . ? C23 Ru1 C20 C26 178.5(4) . . . . ? Cl1 Ru1 C20 C26 -146.4(4) . . . . ? C25 C20 C21 C22 -5.1(5) . . . . ? C26 C20 C21 C22 173.2(3) . . . . ? Ru1 C20 C21 C22 -57.8(3) . . . . ? C25 C20 C21 Ru1 52.7(3) . . . . ? C26 C20 C21 Ru1 -129.0(3) . . . . ? N6 Ru1 C21 C22 170.42(18) . . . . ? N2 Ru1 C21 C22 -114.0(2) . . . . ? C25 Ru1 C21 C22 101.4(2) . . . . ? C24 Ru1 C21 C22 64.1(2) . . . . ? C20 Ru1 C21 C22 131.5(3) . . . . ? C23 Ru1 C21 C22 27.36(19) . . . . ? Cl1 Ru1 C21 C22 -29.7(3) . . . . ? N6 Ru1 C21 C20 38.9(3) . . . . ? N2 Ru1 C21 C20 114.5(2) . . . . ? C25 Ru1 C21 C20 -30.10(19) . . . . ? C24 Ru1 C21 C20 -67.4(2) . . . . ? C22 Ru1 C21 C20 -131.5(3) . . . . ? C23 Ru1 C21 C20 -104.2(2) . . . . ? Cl1 Ru1 C21 C20 -161.24(16) . . . . ? C20 C21 C22 C23 4.6(5) . . . . ? Ru1 C21 C22 C23 -52.6(3) . . . . ? C20 C21 C22 Ru1 57.1(3) . . . . ? N6 Ru1 C22 C23 104.7(5) . . . . ? N2 Ru1 C22 C23 -153.8(2) . . . . ? C25 Ru1 C22 C23 67.1(2) . . . . ? C21 Ru1 C22 C23 134.2(3) . . . . ? C24 Ru1 C22 C23 29.5(2) . . . . ? C20 Ru1 C22 C23 104.5(2) . . . . ? Cl1 Ru1 C22 C23 -64.2(2) . . . . ? N6 Ru1 C22 C21 -29.5(5) . . . . ? N2 Ru1 C22 C21 72.0(2) . . . . ? C25 Ru1 C22 C21 -67.2(2) . . . . ? C24 Ru1 C22 C21 -104.8(2) . . . . ? C20 Ru1 C22 C21 -29.7(2) . . . . ? C23 Ru1 C22 C21 -134.2(3) . . . . ? Cl1 Ru1 C22 C21 161.62(18) . . . . ? C21 C22 C23 C24 -0.6(5) . . . . ? Ru1 C22 C23 C24 -51.6(3) . . . . ? C21 C22 C23 C29 178.0(3) . . . . ? Ru1 C22 C23 C29 127.1(3) . . . . ? C21 C22 C23 Ru1 50.9(3) . . . . ? N6 Ru1 C23 C22 -153.8(2) . . . . ? N2 Ru1 C23 C22 38.6(3) . . . . ? C25 Ru1 C23 C22 -102.0(2) . . . . ? C21 Ru1 C23 C22 -28.2(2) . . . . ? C24 Ru1 C23 C22 -132.1(3) . . . . ? C20 Ru1 C23 C22 -65.1(2) . . . . ? Cl1 Ru1 C23 C22 121.4(2) . . . . ? N6 Ru1 C23 C24 -21.7(3) . . . . ? N2 Ru1 C23 C24 170.74(19) . . . . ? C25 Ru1 C23 C24 30.1(2) . . . . ? C21 Ru1 C23 C24 103.9(2) . . . . ? C20 Ru1 C23 C24 67.0(2) . . . . ? C22 Ru1 C23 C24 132.1(3) . . . . ? Cl1 Ru1 C23 C24 -106.5(2) . . . . ? N6 Ru1 C23 C29 90.5(4) . . . . ? N2 Ru1 C23 C29 -77.1(4) . . . . ? C25 Ru1 C23 C29 142.3(4) . . . . ? C21 Ru1 C23 C29 -143.9(4) . . . . ? C24 Ru1 C23 C29 112.2(5) . . . . ? C20 Ru1 C23 C29 179.2(4) . . . . ? C22 Ru1 C23 C29 -115.7(5) . . . . ? Cl1 Ru1 C23 C29 5.7(4) . . . . ? C22 C23 C24 C25 -2.4(5) . . . . ? C29 C23 C24 C25 178.9(3) . . . . ? Ru1 C23 C24 C25 -55.5(3) . . . . ? C22 C23 C24 Ru1 53.0(3) . . . . ? C29 C23 C24 Ru1 -125.6(3) . . . . ? N6 Ru1 C24 C25 -62.1(2) . . . . ? C21 Ru1 C24 C25 65.8(2) . . . . ? C20 Ru1 C24 C25 28.4(2) . . . . ? C22 Ru1 C24 C25 102.3(2) . . . . ? C23 Ru1 C24 C25 130.9(3) . . . . ? Cl1 Ru1 C24 C25 -151.97(19) . . . . ? N6 Ru1 C24 C23 167.0(2) . . . . ? C25 Ru1 C24 C23 -130.9(3) . . . . ? C21 Ru1 C24 C23 -65.1(2) . . . . ? C20 Ru1 C24 C23 -102.4(2) . . . . ? C22 Ru1 C24 C23 -28.5(2) . . . . ? Cl1 Ru1 C24 C23 77.2(2) . . . . ? C23 C24 C25 C20 1.7(5) . . . . ? Ru1 C24 C25 C20 -55.6(3) . . . . ? C23 C24 C25 Ru1 57.3(3) . . . . ? C21 C20 C25 C24 2.0(5) . . . . ? C26 C20 C25 C24 -176.3(3) . . . . ? Ru1 C20 C25 C24 54.9(3) . . . . ? C21 C20 C25 Ru1 -52.9(3) . . . . ? C26 C20 C25 Ru1 128.8(3) . . . . ? N6 Ru1 C25 C24 123.3(2) . . . . ? N2 Ru1 C25 C24 -167.69(19) . . . . ? C21 Ru1 C25 C24 -103.2(2) . . . . ? C20 Ru1 C25 C24 -133.4(3) . . . . ? C22 Ru1 C25 C24 -65.9(2) . . . . ? C23 Ru1 C25 C24 -29.8(2) . . . . ? Cl1 Ru1 C25 C24 38.8(2) . . . . ? N6 Ru1 C25 C20 -103.3(2) . . . . ? N2 Ru1 C25 C20 -34.3(3) . . . . ? C21 Ru1 C25 C20 30.2(2) . . . . ? C24 Ru1 C25 C20 133.4(3) . . . . ? C22 Ru1 C25 C20 67.5(2) . . . . ? C23 Ru1 C25 C20 103.6(2) . . . . ? Cl1 Ru1 C25 C20 172.20(16) . . . . ? C25 C20 C26 C28 -138.2(4) . . . . ? C21 C20 C26 C28 43.6(5) . . . . ? Ru1 C20 C26 C28 -46.8(6) . . . . ? C25 C20 C26 C27 -8.8(5) . . . . ? C21 C20 C26 C27 173.0(3) . . . . ? Ru1 C20 C26 C27 82.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.020 _refine_diff_density_min -1.694 _refine_diff_density_rms 0.204 # Attachment 'compound5.CIF' data_kcRulig10 _database_code_depnum_ccdc_archive 'CCDC 752545' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 Cl N3 O3 Ru, 3(C H Cl3)' _chemical_formula_sum 'C29 H27 Cl10 N3 O3 Ru' _chemical_formula_weight 921.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5540(2) _cell_length_b 15.2770(3) _cell_length_c 19.4440(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.3070(10) _cell_angle_gamma 90.00 _cell_volume 3613.46(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 17946 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 1.210 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54562 _diffrn_reflns_av_R_equivalents 0.1409 _diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.72 _reflns_number_total 8300 _reflns_number_gt 5999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112--122)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112--122)' _computing_molecular_graphics 'ORTEP-III (Farrugia, 2001)' _computing_publication_material ; local program ; _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^)+(0.0453P)^2^+1.4776P] 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 SHELXL _refine_ls_extinction_coef 0.0006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8300 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Ru1 Ru 0.635015(19) 0.285920(16) 0.031927(12) 0.01954(9) Uani 1 1 d . . . Cl1 Cl 0.61591(6) 0.22467(5) -0.08461(4) 0.02620(18) Uani 1 1 d . . . Cl1S Cl 0.79785(11) 0.02589(12) 0.30157(8) 0.0852(5) Uani 1 1 d . . . Cl2S Cl 0.95447(11) 0.16685(7) 0.30981(6) 0.0580(3) Uani 1 1 d . . . Cl3S Cl 1.02909(11) -0.00578(8) 0.35345(6) 0.0654(3) Uani 1 1 d . . . Cl4S Cl 0.30708(10) 0.18560(7) -0.21169(6) 0.0565(3) Uani 1 1 d . . . Cl5S Cl 0.27273(9) 0.35615(9) -0.15715(6) 0.0637(3) Uani 1 1 d . . . Cl6S Cl 0.37926(10) 0.34082(7) -0.27204(6) 0.0593(3) Uani 1 1 d . . . Cl7S Cl 0.12846(8) 0.48240(7) -0.31889(6) 0.0494(3) Uani 1 1 d . . . Cl8S Cl -0.03592(9) 0.61775(7) -0.32639(6) 0.0528(3) Uani 1 1 d . . . Cl9S Cl 0.07326(10) 0.59929(7) -0.43980(7) 0.0600(3) Uani 1 1 d . . . O1 O 0.84778(17) 0.08469(14) 0.12316(12) 0.0296(5) Uani 1 1 d . . . O2 O 1.2040(2) 0.38836(19) 0.00421(14) 0.0484(7) Uani 1 1 d . . . O3 O 1.2721(2) 0.34000(18) 0.11094(14) 0.0435(6) Uani 1 1 d . . . N1 N 0.5768(2) 0.16211(16) 0.05561(12) 0.0201(5) Uani 1 1 d . . . N2 N 0.7798(2) 0.21310(16) 0.06472(13) 0.0211(5) Uani 1 1 d . . . N3 N 1.1946(2) 0.34996(19) 0.05865(16) 0.0330(7) Uani 1 1 d . . . C1 C 0.4678(2) 0.1352(2) 0.04218(16) 0.0231(6) Uani 1 1 d . . . C2 C 0.3827(3) 0.1863(2) 0.00064(17) 0.0270(7) Uani 1 1 d . . . H2 H 0.3998 0.2392 -0.0200 0.032 Uiso 1 1 calc R . . C3 C 0.2753(3) 0.1604(2) -0.01028(18) 0.0314(8) Uani 1 1 d . . . H3 H 0.2185 0.1956 -0.0383 0.038 Uiso 1 1 calc R . . C4 C 0.2485(3) 0.0820(2) 0.01956(18) 0.0345(8) Uani 1 1 d . . . H4 H 0.1736 0.0659 0.0132 0.041 Uiso 1 1 calc R . . C5 C 0.3301(3) 0.0288(2) 0.05778(17) 0.0323(8) Uani 1 1 d . . . H5 H 0.3114 -0.0248 0.0766 0.039 Uiso 1 1 calc R . . C6 C 0.4413(3) 0.0532(2) 0.06932(16) 0.0262(7) Uani 1 1 d . . . C7 C 0.5275(3) -0.0020(2) 0.10469(16) 0.0268(7) Uani 1 1 d . . . H7 H 0.5117 -0.0568 0.1229 0.032 Uiso 1 1 calc R . . C8 C 0.6339(3) 0.0238(2) 0.11265(16) 0.0271(7) Uani 1 1 d . . . H8 H 0.6926 -0.0138 0.1348 0.033 Uiso 1 1 calc R . . C9 C 0.6558(2) 0.10676(19) 0.08773(16) 0.0219(6) Uani 1 1 d . . . C10 C 0.7719(2) 0.1344(2) 0.09463(16) 0.0232(7) Uani 1 1 d . . . C11 C 0.8850(2) 0.2466(2) 0.06451(16) 0.0226(6) Uani 1 1 d . . . C12 C 0.8983(3) 0.2924(2) 0.00514(17) 0.0260(7) Uani 1 1 d . . . H12 H 0.8370 0.3000 -0.0343 0.031 Uiso 1 1 calc R . . C13 C 0.9991(3) 0.3270(2) 0.00260(17) 0.0281(7) Uani 1 1 d . . . H13 H 1.0075 0.3582 -0.0380 0.034 Uiso 1 1 calc R . . C14 C 1.0874(3) 0.3151(2) 0.06041(17) 0.0267(7) Uani 1 1 d . . . C15 C 1.0774(3) 0.2701(2) 0.12089(18) 0.0313(8) Uani 1 1 d . . . H15 H 1.1390 0.2627 0.1601 0.038 Uiso 1 1 calc R . . C16 C 0.9760(3) 0.2365(2) 0.12253(18) 0.0289(7) Uani 1 1 d . . . H16 H 0.9678 0.2062 0.1636 0.035 Uiso 1 1 calc R . . C17 C 0.5731(4) 0.3996(3) 0.24026(19) 0.0492(11) Uani 1 1 d . . . H17A H 0.6256 0.4480 0.2448 0.074 Uiso 1 1 calc R . . H17B H 0.5713 0.3785 0.2876 0.074 Uiso 1 1 calc R . . H17C H 0.4997 0.4200 0.2152 0.074 Uiso 1 1 calc R . . C18 C 0.6085(3) 0.3249(2) 0.19828(18) 0.0339(8) Uani 1 1 d . . . H18 H 0.5505 0.2786 0.1916 0.041 Uiso 1 1 calc R . . C19 C 0.7150(4) 0.2844(3) 0.2397(2) 0.0539(12) Uani 1 1 d . . . H19A H 0.7382 0.2391 0.2108 0.081 Uiso 1 1 calc R . . H19B H 0.7039 0.2581 0.2834 0.081 Uiso 1 1 calc R . . H19C H 0.7718 0.3297 0.2517 0.081 Uiso 1 1 calc R . . C20 C 0.6115(3) 0.3577(2) 0.12547(16) 0.0251(7) Uani 1 1 d . . . C21 C 0.5124(3) 0.3597(2) 0.07041(17) 0.0259(7) Uani 1 1 d . . . H21 H 0.4463 0.3396 0.0805 0.031 Uiso 1 1 calc R . . C22 C 0.5093(3) 0.3901(2) 0.00212(17) 0.0280(7) Uani 1 1 d . . . H22 H 0.4414 0.3912 -0.0329 0.034 Uiso 1 1 calc R . . C23 C 0.6071(3) 0.4194(2) -0.01540(17) 0.0293(7) Uani 1 1 d . . . C24 C 0.6060(4) 0.4458(2) -0.09014(18) 0.0430(10) Uani 1 1 d . . . H24A H 0.6389 0.5040 -0.0898 0.065 Uiso 1 1 calc R . . H24B H 0.5301 0.4471 -0.1190 0.065 Uiso 1 1 calc R . . H24C H 0.6485 0.4034 -0.1103 0.065 Uiso 1 1 calc R . . C25 C 0.7058(3) 0.4183(2) 0.03818(17) 0.0281(7) Uani 1 1 d . . . H25 H 0.7717 0.4388 0.0280 0.034 Uiso 1 1 calc R . . C26 C 0.7082(3) 0.3867(2) 0.10753(17) 0.0267(7) Uani 1 1 d . . . H26 H 0.7761 0.3851 0.1424 0.032 Uiso 1 1 calc R . . C1S C 0.9285(3) 0.0551(2) 0.29367(19) 0.0374(8) Uani 1 1 d . . . H1S H 0.9338 0.0416 0.2443 0.045 Uiso 1 1 calc R . . C2S C 0.3608(3) 0.2916(3) -0.1945(2) 0.0419(9) Uani 1 1 d . . . H2S H 0.4339 0.2876 -0.1596 0.050 Uiso 1 1 calc R . . C3S C 0.0230(3) 0.5437(2) -0.3753(2) 0.0377(8) Uani 1 1 d . . . H3S H -0.0355 0.5022 -0.4002 0.045 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 0.01914(14) 0.01848(14) 0.02099(14) 0.00062(10) 0.00494(9) -0.00011(10) Cl1 0.0296(4) 0.0264(4) 0.0216(4) -0.0022(3) 0.0044(3) 0.0008(3) Cl1S 0.0522(8) 0.1293(13) 0.0781(9) 0.0068(9) 0.0240(7) -0.0233(8) Cl2S 0.0881(8) 0.0406(6) 0.0404(6) 0.0033(5) 0.0067(5) 0.0042(5) Cl3S 0.0753(8) 0.0596(7) 0.0554(7) 0.0129(6) 0.0047(6) 0.0254(6) Cl4S 0.0600(7) 0.0485(6) 0.0522(6) 0.0116(5) -0.0030(5) -0.0048(5) Cl5S 0.0492(6) 0.0873(9) 0.0498(6) -0.0097(6) 0.0030(5) 0.0238(6) Cl6S 0.0726(8) 0.0469(6) 0.0624(7) 0.0100(5) 0.0243(6) 0.0050(5) Cl7S 0.0393(5) 0.0446(6) 0.0608(6) 0.0112(5) 0.0058(5) 0.0074(4) Cl8S 0.0523(6) 0.0382(6) 0.0710(7) -0.0017(5) 0.0207(5) 0.0051(4) Cl9S 0.0567(7) 0.0526(7) 0.0785(8) 0.0269(6) 0.0318(6) 0.0004(5) O1 0.0223(12) 0.0253(12) 0.0398(13) 0.0061(10) 0.0048(10) 0.0031(9) O2 0.0397(16) 0.0596(18) 0.0497(17) 0.0082(14) 0.0183(13) -0.0176(13) O3 0.0243(13) 0.0565(18) 0.0475(16) 0.0029(13) 0.0048(12) -0.0081(12) N1 0.0207(13) 0.0193(13) 0.0199(13) -0.0009(10) 0.0043(10) -0.0015(10) N2 0.0190(13) 0.0209(13) 0.0229(13) 0.0001(11) 0.0043(10) -0.0011(10) N3 0.0284(16) 0.0314(16) 0.0423(18) -0.0025(14) 0.0146(14) -0.0063(13) C1 0.0216(15) 0.0241(16) 0.0234(16) -0.0033(13) 0.0055(13) -0.0016(12) C2 0.0246(17) 0.0254(17) 0.0293(17) -0.0026(14) 0.0034(13) -0.0009(13) C3 0.0222(17) 0.035(2) 0.0338(19) -0.0040(15) 0.0007(14) -0.0015(14) C4 0.0202(17) 0.045(2) 0.038(2) -0.0059(17) 0.0063(15) -0.0097(15) C5 0.0303(18) 0.036(2) 0.0318(18) -0.0034(15) 0.0105(15) -0.0107(15) C6 0.0272(17) 0.0268(17) 0.0243(16) -0.0016(13) 0.0060(13) -0.0035(13) C7 0.0342(18) 0.0225(16) 0.0260(17) 0.0044(13) 0.0115(14) -0.0046(14) C8 0.0291(18) 0.0241(17) 0.0264(17) 0.0011(14) 0.0035(14) 0.0016(13) C9 0.0232(16) 0.0175(15) 0.0257(16) -0.0008(12) 0.0077(13) -0.0019(12) C10 0.0213(16) 0.0242(17) 0.0238(16) -0.0010(13) 0.0049(13) 0.0016(13) C11 0.0193(15) 0.0209(15) 0.0292(17) -0.0028(13) 0.0090(13) 0.0000(12) C12 0.0217(16) 0.0308(18) 0.0253(16) 0.0011(14) 0.0056(13) -0.0007(13) C13 0.0309(18) 0.0283(18) 0.0280(17) -0.0001(14) 0.0128(14) -0.0028(14) C14 0.0204(16) 0.0293(18) 0.0314(18) -0.0020(14) 0.0081(14) -0.0042(13) C15 0.0223(17) 0.038(2) 0.0307(18) 0.0051(15) 0.0005(14) -0.0020(14) C16 0.0270(17) 0.0304(18) 0.0294(17) 0.0063(14) 0.0069(14) -0.0022(14) C17 0.072(3) 0.054(3) 0.027(2) 0.0034(18) 0.0215(19) 0.022(2) C18 0.048(2) 0.0300(19) 0.0259(17) 0.0022(15) 0.0132(16) 0.0039(16) C19 0.074(3) 0.056(3) 0.033(2) 0.0069(19) 0.015(2) 0.028(2) C20 0.0325(17) 0.0203(16) 0.0236(16) -0.0024(13) 0.0089(13) 0.0023(13) C21 0.0217(16) 0.0248(17) 0.0323(18) -0.0027(14) 0.0085(14) 0.0026(13) C22 0.0281(17) 0.0225(17) 0.0296(18) -0.0009(14) 0.0000(14) 0.0063(13) C23 0.042(2) 0.0182(16) 0.0292(17) 0.0003(14) 0.0123(15) 0.0035(14) C24 0.072(3) 0.029(2) 0.032(2) 0.0087(16) 0.0195(19) 0.0054(18) C25 0.0287(17) 0.0216(16) 0.0384(19) -0.0005(14) 0.0167(15) -0.0019(13) C26 0.0273(17) 0.0197(16) 0.0300(17) -0.0052(13) 0.0010(14) -0.0016(13) C1S 0.040(2) 0.038(2) 0.0337(19) 0.0026(16) 0.0093(16) 0.0047(16) C2S 0.035(2) 0.046(2) 0.040(2) 0.0011(18) 0.0008(16) 0.0060(17) C3S 0.0334(19) 0.0317(19) 0.048(2) 0.0077(17) 0.0103(17) -0.0017(15) _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 N2 2.092(2) . ? Ru1 N1 2.119(2) . ? Ru1 C26 2.170(3) . ? Ru1 C21 2.183(3) . ? Ru1 C25 2.200(3) . ? Ru1 C20 2.206(3) . ? Ru1 C22 2.215(3) . ? Ru1 C23 2.230(3) . ? Ru1 Cl1 2.4081(8) . ? Cl1S C1S 1.743(4) . ? Cl2S C1S 1.752(4) . ? Cl3S C1S 1.757(4) . ? Cl4S C2S 1.755(4) . ? Cl5S C2S 1.766(4) . ? Cl6S C2S 1.750(4) . ? Cl7S C3S 1.765(4) . ? Cl8S C3S 1.756(4) . ? Cl9S C3S 1.755(4) . ? O1 C10 1.238(4) . ? O2 N3 1.241(4) . ? O3 N3 1.231(4) . ? N1 C9 1.335(4) . ? N1 C1 1.391(4) . ? N2 C10 1.350(4) . ? N2 C11 1.417(4) . ? N3 C14 1.455(4) . ? C1 C2 1.406(4) . ? C1 C6 1.429(4) . ? C2 C3 1.371(4) . ? C2 H2 0.9500 . ? C3 C4 1.407(5) . ? C3 H3 0.9500 . ? C4 C5 1.373(5) . ? C4 H4 0.9500 . ? C5 C6 1.409(4) . ? C5 H5 0.9500 . ? C6 C7 1.410(5) . ? C7 C8 1.364(4) . ? C7 H7 0.9500 . ? C8 C9 1.408(4) . ? C8 H8 0.9500 . ? C9 C10 1.491(4) . ? C11 C12 1.395(4) . ? C11 C16 1.402(4) . ? C12 C13 1.384(4) . ? C12 H12 0.9500 . ? C13 C14 1.382(5) . ? C13 H13 0.9500 . ? C14 C15 1.395(5) . ? C15 C16 1.379(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.531(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C20 1.511(4) . ? C18 C19 1.512(5) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C26 1.415(4) . ? C20 C21 1.426(4) . ? C21 C22 1.398(5) . ? C21 H21 0.9500 . ? C22 C23 1.425(5) . ? C22 H22 0.9500 . ? C23 C25 1.409(5) . ? C23 C24 1.505(5) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.426(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C1S H1S 1.0000 . ? C2S H2S 1.0000 . ? C3S H3S 1.0000 . ? 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 N2 Ru1 N1 77.26(9) . . ? N2 Ru1 C26 88.87(11) . . ? N1 Ru1 C26 126.67(11) . . ? N2 Ru1 C21 143.42(11) . . ? N1 Ru1 C21 94.37(10) . . ? C26 Ru1 C21 67.53(12) . . ? N2 Ru1 C25 99.38(11) . . ? N1 Ru1 C25 164.74(11) . . ? C26 Ru1 C25 38.07(12) . . ? C21 Ru1 C25 79.40(12) . . ? N2 Ru1 C20 107.26(11) . . ? N1 Ru1 C20 98.10(10) . . ? C26 Ru1 C20 37.72(12) . . ? C21 Ru1 C20 37.93(12) . . ? C25 Ru1 C20 68.42(11) . . ? N2 Ru1 C22 166.19(11) . . ? N1 Ru1 C22 115.87(11) . . ? C26 Ru1 C22 79.77(12) . . ? C21 Ru1 C22 37.05(12) . . ? C25 Ru1 C22 66.82(12) . . ? C20 Ru1 C22 68.06(12) . . ? N2 Ru1 C23 130.44(11) . . ? N1 Ru1 C23 151.49(11) . . ? C26 Ru1 C23 68.13(12) . . ? C21 Ru1 C23 67.47(12) . . ? C25 Ru1 C23 37.08(12) . . ? C20 Ru1 C23 81.13(11) . . ? C22 Ru1 C23 37.39(12) . . ? N2 Ru1 Cl1 87.54(7) . . ? N1 Ru1 Cl1 84.15(7) . . ? C26 Ru1 Cl1 147.17(9) . . ? C21 Ru1 Cl1 127.47(9) . . ? C25 Ru1 Cl1 110.73(8) . . ? C20 Ru1 Cl1 165.18(9) . . ? C22 Ru1 Cl1 97.71(9) . . ? C23 Ru1 Cl1 89.90(8) . . ? C9 N1 C1 118.9(3) . . ? C9 N1 Ru1 114.26(19) . . ? C1 N1 Ru1 126.8(2) . . ? C10 N2 C11 119.4(3) . . ? C10 N2 Ru1 116.97(19) . . ? C11 N2 Ru1 123.20(19) . . ? O3 N3 O2 122.7(3) . . ? O3 N3 C14 118.8(3) . . ? O2 N3 C14 118.4(3) . . ? N1 C1 C2 121.1(3) . . ? N1 C1 C6 119.9(3) . . ? C2 C1 C6 119.1(3) . . ? C3 C2 C1 120.5(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C7 122.1(3) . . ? C5 C6 C1 119.0(3) . . ? C7 C6 C1 118.9(3) . . ? C8 C7 C6 119.6(3) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 119.4(3) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? N1 C9 C8 123.0(3) . . ? N1 C9 C10 117.3(3) . . ? C8 C9 C10 119.6(3) . . ? O1 C10 N2 127.5(3) . . ? O1 C10 C9 119.6(3) . . ? N2 C10 C9 112.9(3) . . ? C12 C11 C16 118.7(3) . . ? C12 C11 N2 119.0(3) . . ? C16 C11 N2 122.2(3) . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C12 118.5(3) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C15 122.0(3) . . ? C13 C14 N3 119.5(3) . . ? C15 C14 N3 118.5(3) . . ? C16 C15 C14 118.6(3) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C11 120.9(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C20 C18 C19 114.3(3) . . ? C20 C18 C17 109.3(3) . . ? C19 C18 C17 110.9(3) . . ? C20 C18 H18 107.4 . . ? C19 C18 H18 107.4 . . ? C17 C18 H18 107.4 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C26 C20 C21 116.7(3) . . ? C26 C20 C18 123.8(3) . . ? C21 C20 C18 119.4(3) . . ? C26 C20 Ru1 69.76(17) . . ? C21 C20 Ru1 70.18(17) . . ? C18 C20 Ru1 130.3(2) . . ? C22 C21 C20 122.3(3) . . ? C22 C21 Ru1 72.73(18) . . ? C20 C21 Ru1 71.89(17) . . ? C22 C21 H21 118.8 . . ? C20 C21 H21 118.8 . . ? Ru1 C21 H21 129.1 . . ? C21 C22 C23 120.5(3) . . ? C21 C22 Ru1 70.22(18) . . ? C23 C22 Ru1 71.84(18) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? Ru1 C22 H22 130.9 . . ? C25 C23 C22 118.2(3) . . ? C25 C23 C24 120.9(3) . . ? C22 C23 C24 120.8(3) . . ? C25 C23 Ru1 70.34(18) . . ? C22 C23 Ru1 70.77(18) . . ? C24 C23 Ru1 127.3(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 C26 120.8(3) . . ? C23 C25 Ru1 72.58(19) . . ? C26 C25 Ru1 69.79(17) . . ? C23 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? Ru1 C25 H25 130.7 . . ? C20 C26 C25 121.4(3) . . ? C20 C26 Ru1 72.52(18) . . ? C25 C26 Ru1 72.13(18) . . ? C20 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? Ru1 C26 H26 128.3 . . ? Cl1S C1S Cl2S 111.8(2) . . ? Cl1S C1S Cl3S 110.2(2) . . ? Cl2S C1S Cl3S 109.0(2) . . ? Cl1S C1S H1S 108.6 . . ? Cl2S C1S H1S 108.6 . . ? Cl3S C1S H1S 108.6 . . ? Cl6S C2S Cl4S 111.0(2) . . ? Cl6S C2S Cl5S 110.1(2) . . ? Cl4S C2S Cl5S 110.1(2) . . ? Cl6S C2S H2S 108.5 . . ? Cl4S C2S H2S 108.5 . . ? Cl5S C2S H2S 108.5 . . ? Cl9S C3S Cl8S 110.4(2) . . ? Cl9S C3S Cl7S 110.8(2) . . ? Cl8S C3S Cl7S 110.9(2) . . ? Cl9S C3S H3S 108.2 . . ? Cl8S C3S H3S 108.2 . . ? Cl7S C3S H3S 108.2 . . ? 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 N2 Ru1 N1 C9 9.2(2) . . . . ? C26 Ru1 N1 C9 -69.7(2) . . . . ? C21 Ru1 N1 C9 -134.8(2) . . . . ? C25 Ru1 N1 C9 -69.7(5) . . . . ? C20 Ru1 N1 C9 -96.8(2) . . . . ? C22 Ru1 N1 C9 -166.3(2) . . . . ? C23 Ru1 N1 C9 176.9(2) . . . . ? Cl1 Ru1 N1 C9 98.0(2) . . . . ? N2 Ru1 N1 C1 -171.9(2) . . . . ? C26 Ru1 N1 C1 109.2(2) . . . . ? C21 Ru1 N1 C1 44.1(2) . . . . ? C25 Ru1 N1 C1 109.2(4) . . . . ? C20 Ru1 N1 C1 82.1(2) . . . . ? C22 Ru1 N1 C1 12.6(3) . . . . ? C23 Ru1 N1 C1 -4.2(4) . . . . ? Cl1 Ru1 N1 C1 -83.1(2) . . . . ? N1 Ru1 N2 C10 -10.5(2) . . . . ? C26 Ru1 N2 C10 117.6(2) . . . . ? C21 Ru1 N2 C10 69.5(3) . . . . ? C25 Ru1 N2 C10 154.4(2) . . . . ? C20 Ru1 N2 C10 84.2(2) . . . . ? C22 Ru1 N2 C10 152.1(4) . . . . ? C23 Ru1 N2 C10 177.2(2) . . . . ? Cl1 Ru1 N2 C10 -95.0(2) . . . . ? N1 Ru1 N2 C11 177.1(2) . . . . ? C26 Ru1 N2 C11 -54.8(2) . . . . ? C21 Ru1 N2 C11 -102.9(3) . . . . ? C25 Ru1 N2 C11 -18.1(2) . . . . ? C20 Ru1 N2 C11 -88.2(2) . . . . ? C22 Ru1 N2 C11 -20.3(6) . . . . ? C23 Ru1 N2 C11 4.8(3) . . . . ? Cl1 Ru1 N2 C11 92.5(2) . . . . ? C9 N1 C1 C2 -171.8(3) . . . . ? Ru1 N1 C1 C2 9.4(4) . . . . ? C9 N1 C1 C6 6.6(4) . . . . ? Ru1 N1 C1 C6 -172.3(2) . . . . ? N1 C1 C2 C3 -177.9(3) . . . . ? C6 C1 C2 C3 3.7(5) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 -2.5(5) . . . . ? C3 C4 C5 C6 1.9(5) . . . . ? C4 C5 C6 C7 -176.2(3) . . . . ? C4 C5 C6 C1 1.6(5) . . . . ? N1 C1 C6 C5 177.3(3) . . . . ? C2 C1 C6 C5 -4.3(4) . . . . ? N1 C1 C6 C7 -4.9(4) . . . . ? C2 C1 C6 C7 173.5(3) . . . . ? C5 C6 C7 C8 178.1(3) . . . . ? C1 C6 C7 C8 0.3(5) . . . . ? C6 C7 C8 C9 2.4(5) . . . . ? C1 N1 C9 C8 -3.9(4) . . . . ? Ru1 N1 C9 C8 175.1(2) . . . . ? C1 N1 C9 C10 174.0(2) . . . . ? Ru1 N1 C9 C10 -7.1(3) . . . . ? C7 C8 C9 N1 -0.6(5) . . . . ? C7 C8 C9 C10 -178.5(3) . . . . ? C11 N2 C10 O1 -0.3(5) . . . . ? Ru1 N2 C10 O1 -173.1(3) . . . . ? C11 N2 C10 C9 -177.5(2) . . . . ? Ru1 N2 C10 C9 9.8(3) . . . . ? N1 C9 C10 O1 -179.0(3) . . . . ? C8 C9 C10 O1 -1.1(4) . . . . ? N1 C9 C10 N2 -1.6(4) . . . . ? C8 C9 C10 N2 176.3(3) . . . . ? C10 N2 C11 C12 142.2(3) . . . . ? Ru1 N2 C11 C12 -45.5(4) . . . . ? C10 N2 C11 C16 -38.9(4) . . . . ? Ru1 N2 C11 C16 133.3(3) . . . . ? C16 C11 C12 C13 0.5(5) . . . . ? N2 C11 C12 C13 179.4(3) . . . . ? C11 C12 C13 C14 0.1(5) . . . . ? C12 C13 C14 C15 -0.4(5) . . . . ? C12 C13 C14 N3 179.2(3) . . . . ? O3 N3 C14 C13 179.0(3) . . . . ? O2 N3 C14 C13 -1.3(5) . . . . ? O3 N3 C14 C15 -1.3(5) . . . . ? O2 N3 C14 C15 178.4(3) . . . . ? C13 C14 C15 C16 0.1(5) . . . . ? N3 C14 C15 C16 -179.6(3) . . . . ? C14 C15 C16 C11 0.6(5) . . . . ? C12 C11 C16 C15 -0.9(5) . . . . ? N2 C11 C16 C15 -179.8(3) . . . . ? C19 C18 C20 C26 -27.9(5) . . . . ? C17 C18 C20 C26 96.9(4) . . . . ? C19 C18 C20 C21 151.6(3) . . . . ? C17 C18 C20 C21 -83.6(4) . . . . ? C19 C18 C20 Ru1 63.4(4) . . . . ? C17 C18 C20 Ru1 -171.8(3) . . . . ? N2 Ru1 C20 C26 64.20(19) . . . . ? N1 Ru1 C20 C26 143.30(18) . . . . ? C21 Ru1 C20 C26 -130.0(3) . . . . ? C25 Ru1 C20 C26 -29.28(19) . . . . ? C22 Ru1 C20 C26 -102.0(2) . . . . ? C23 Ru1 C20 C26 -65.51(19) . . . . ? Cl1 Ru1 C20 C26 -118.9(3) . . . . ? N2 Ru1 C20 C21 -165.81(17) . . . . ? N1 Ru1 C20 C21 -86.70(19) . . . . ? C26 Ru1 C20 C21 130.0(3) . . . . ? C25 Ru1 C20 C21 100.7(2) . . . . ? C22 Ru1 C20 C21 28.00(18) . . . . ? C23 Ru1 C20 C21 64.48(19) . . . . ? Cl1 Ru1 C20 C21 11.1(4) . . . . ? N2 Ru1 C20 C18 -53.5(3) . . . . ? N1 Ru1 C20 C18 25.6(3) . . . . ? C26 Ru1 C20 C18 -117.7(4) . . . . ? C21 Ru1 C20 C18 112.3(4) . . . . ? C25 Ru1 C20 C18 -147.0(3) . . . . ? C22 Ru1 C20 C18 140.3(3) . . . . ? C23 Ru1 C20 C18 176.8(3) . . . . ? Cl1 Ru1 C20 C18 123.4(3) . . . . ? C26 C20 C21 C22 -1.2(5) . . . . ? C18 C20 C21 C22 179.3(3) . . . . ? Ru1 C20 C21 C22 -54.8(3) . . . . ? C26 C20 C21 Ru1 53.6(2) . . . . ? C18 C20 C21 Ru1 -125.9(3) . . . . ? N2 Ru1 C21 C22 156.86(19) . . . . ? N1 Ru1 C21 C22 -128.69(19) . . . . ? C26 Ru1 C21 C22 103.2(2) . . . . ? C25 Ru1 C21 C22 65.4(2) . . . . ? C20 Ru1 C21 C22 133.7(3) . . . . ? C23 Ru1 C21 C22 28.60(19) . . . . ? Cl1 Ru1 C21 C22 -42.7(2) . . . . ? N2 Ru1 C21 C20 23.1(3) . . . . ? N1 Ru1 C21 C20 97.58(18) . . . . ? C26 Ru1 C21 C20 -30.48(18) . . . . ? C25 Ru1 C21 C20 -68.36(19) . . . . ? C22 Ru1 C21 C20 -133.7(3) . . . . ? C23 Ru1 C21 C20 -105.1(2) . . . . ? Cl1 Ru1 C21 C20 -176.44(14) . . . . ? C20 C21 C22 C23 1.0(5) . . . . ? Ru1 C21 C22 C23 -53.4(3) . . . . ? C20 C21 C22 Ru1 54.4(3) . . . . ? N2 Ru1 C22 C21 -101.2(5) . . . . ? N1 Ru1 C22 C21 59.9(2) . . . . ? C26 Ru1 C22 C21 -66.1(2) . . . . ? C25 Ru1 C22 C21 -103.6(2) . . . . ? C20 Ru1 C22 C21 -28.61(19) . . . . ? C23 Ru1 C22 C21 -133.3(3) . . . . ? Cl1 Ru1 C22 C21 147.09(18) . . . . ? N2 Ru1 C22 C23 32.1(5) . . . . ? N1 Ru1 C22 C23 -166.84(17) . . . . ? C26 Ru1 C22 C23 67.22(19) . . . . ? C21 Ru1 C22 C23 133.3(3) . . . . ? C25 Ru1 C22 C23 29.68(18) . . . . ? C20 Ru1 C22 C23 104.7(2) . . . . ? Cl1 Ru1 C22 C23 -79.63(18) . . . . ? C21 C22 C23 C25 -1.1(5) . . . . ? Ru1 C22 C23 C25 -53.8(3) . . . . ? C21 C22 C23 C24 175.3(3) . . . . ? Ru1 C22 C23 C24 122.6(3) . . . . ? C21 C22 C23 Ru1 52.7(3) . . . . ? N2 Ru1 C23 C25 -39.4(2) . . . . ? N1 Ru1 C23 C25 156.4(2) . . . . ? C26 Ru1 C23 C25 28.86(18) . . . . ? C21 Ru1 C23 C25 102.6(2) . . . . ? C20 Ru1 C23 C25 65.73(19) . . . . ? C22 Ru1 C23 C25 131.0(3) . . . . ? Cl1 Ru1 C23 C25 -126.12(17) . . . . ? N2 Ru1 C23 C22 -170.42(17) . . . . ? N1 Ru1 C23 C22 25.4(3) . . . . ? C26 Ru1 C23 C22 -102.1(2) . . . . ? C21 Ru1 C23 C22 -28.35(18) . . . . ? C25 Ru1 C23 C22 -131.0(3) . . . . ? C20 Ru1 C23 C22 -65.26(19) . . . . ? Cl1 Ru1 C23 C22 102.90(18) . . . . ? N2 Ru1 C23 C24 75.0(4) . . . . ? N1 Ru1 C23 C24 -89.2(4) . . . . ? C26 Ru1 C23 C24 143.2(4) . . . . ? C21 Ru1 C23 C24 -143.0(4) . . . . ? C25 Ru1 C23 C24 114.4(4) . . . . ? C20 Ru1 C23 C24 -179.9(3) . . . . ? C22 Ru1 C23 C24 -114.6(4) . . . . ? Cl1 Ru1 C23 C24 -11.7(3) . . . . ? C22 C23 C25 C26 1.4(5) . . . . ? C24 C23 C25 C26 -174.9(3) . . . . ? Ru1 C23 C25 C26 -52.5(3) . . . . ? C22 C23 C25 Ru1 54.0(3) . . . . ? C24 C23 C25 Ru1 -122.4(3) . . . . ? N2 Ru1 C25 C23 150.66(18) . . . . ? N1 Ru1 C25 C23 -133.4(4) . . . . ? C26 Ru1 C25 C23 -133.4(3) . . . . ? C21 Ru1 C25 C23 -66.48(19) . . . . ? C20 Ru1 C25 C23 -104.4(2) . . . . ? C22 Ru1 C25 C23 -29.91(18) . . . . ? Cl1 Ru1 C25 C23 59.74(18) . . . . ? N2 Ru1 C25 C26 -75.92(19) . . . . ? N1 Ru1 C25 C26 0.0(5) . . . . ? C21 Ru1 C25 C26 66.94(19) . . . . ? C20 Ru1 C25 C26 29.03(18) . . . . ? C22 Ru1 C25 C26 103.5(2) . . . . ? C23 Ru1 C25 C26 133.4(3) . . . . ? Cl1 Ru1 C25 C26 -166.85(16) . . . . ? C21 C20 C26 C25 1.5(4) . . . . ? C18 C20 C26 C25 -179.0(3) . . . . ? Ru1 C20 C26 C25 55.3(3) . . . . ? C21 C20 C26 Ru1 -53.8(2) . . . . ? C18 C20 C26 Ru1 125.7(3) . . . . ? C23 C25 C26 C20 -1.7(5) . . . . ? Ru1 C25 C26 C20 -55.5(3) . . . . ? C23 C25 C26 Ru1 53.8(3) . . . . ? N2 Ru1 C26 C20 -120.69(19) . . . . ? N1 Ru1 C26 C20 -47.5(2) . . . . ? C21 Ru1 C26 C20 30.64(18) . . . . ? C25 Ru1 C26 C20 132.5(3) . . . . ? C22 Ru1 C26 C20 67.22(19) . . . . ? C23 Ru1 C26 C20 104.3(2) . . . . ? Cl1 Ru1 C26 C20 155.60(15) . . . . ? N2 Ru1 C26 C25 106.83(19) . . . . ? N1 Ru1 C26 C25 179.99(16) . . . . ? C21 Ru1 C26 C25 -101.8(2) . . . . ? C20 Ru1 C26 C25 -132.5(3) . . . . ? C22 Ru1 C26 C25 -65.27(19) . . . . ? C23 Ru1 C26 C25 -28.16(18) . . . . ? Cl1 Ru1 C26 C25 23.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.72 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.701 _refine_diff_density_min -1.120 _refine_diff_density_rms 0.125 # Attachment 'compound6.CIF' data_kcbzrupic _database_code_depnum_ccdc_archive 'CCDC 752546' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Cl N O2 Ru' _chemical_formula_sum 'C12 H10 Cl N O2 Ru' _chemical_formula_weight 336.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3799(2) _cell_length_b 8.5718(3) _cell_length_c 10.8540(3) _cell_angle_alpha 75.937(2) _cell_angle_beta 77.251(2) _cell_angle_gamma 79.785(2) _cell_volume 556.77(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12481 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.008 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 1.633 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9666 _diffrn_reflns_av_R_equivalents 0.0815 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2499 _reflns_number_gt 2378 _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/[\s^2^(Fo^2^)+(0.0333P)^2^+0.6140P] 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 2499 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.67405(3) 0.77080(2) 0.674614(18) 0.02285(11) Uani 1 1 d . . . Cl1 Cl 0.29496(12) 0.81038(9) 0.77086(7) 0.03006(17) Uani 1 1 d . . . O1 O 0.6807(4) 1.0114(2) 0.6763(2) 0.0287(4) Uani 1 1 d . . . C1 C 0.8231(6) 0.5263(4) 0.6567(3) 0.0343(7) Uani 1 1 d . . . H1 H 0.8432 0.4300 0.7206 0.041 Uiso 1 1 calc R . . O2 O 0.7447(5) 1.1770(3) 0.7896(3) 0.0439(6) Uani 1 1 d . . . C2 C 0.6351(6) 0.5633(4) 0.6029(3) 0.0384(7) Uani 1 1 d . . . H2 H 0.5261 0.4933 0.6316 0.046 Uiso 1 1 calc R . . C3 C 0.6075(6) 0.7055(5) 0.5053(3) 0.0423(8) Uani 1 1 d . . . H3 H 0.4807 0.7303 0.4682 0.051 Uiso 1 1 calc R . . C4 C 0.7674(7) 0.8088(4) 0.4640(3) 0.0404(8) Uani 1 1 d . . . H4 H 0.7501 0.9035 0.3982 0.049 Uiso 1 1 calc R . . C5 C 0.9556(6) 0.7722(4) 0.5203(3) 0.0360(7) Uani 1 1 d . . . H5 H 1.0635 0.8432 0.4928 0.043 Uiso 1 1 calc R . . C6 C 0.9826(5) 0.6329(4) 0.6157(3) 0.0328(6) Uani 1 1 d . . . H6 H 1.1086 0.6092 0.6534 0.039 Uiso 1 1 calc R . . C7 C 0.7319(5) 0.6203(4) 0.9549(3) 0.0299(6) Uani 1 1 d . . . H7 H 0.7166 0.5201 0.9371 0.036 Uiso 1 1 calc R . . C8 C 0.7624(6) 0.6239(4) 1.0772(3) 0.0377(7) Uani 1 1 d . . . H8 H 0.7688 0.5270 1.1420 0.045 Uiso 1 1 calc R . . C9 C 0.7832(6) 0.7697(5) 1.1034(3) 0.0389(7) Uani 1 1 d . . . H9 H 0.8056 0.7742 1.1861 0.047 Uiso 1 1 calc R . . C10 C 0.7711(5) 0.9097(4) 1.0072(3) 0.0344(7) Uani 1 1 d . . . H10 H 0.7823 1.0118 1.0233 0.041 Uiso 1 1 calc R . . C11 C 0.7425(5) 0.8974(4) 0.8880(3) 0.0277(6) Uani 1 1 d . . . C12 C 0.7224(5) 1.0434(4) 0.7779(3) 0.0299(6) Uani 1 1 d . . . N14 N 0.7235(4) 0.7559(3) 0.8611(2) 0.0254(5) 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 Ru1 0.02511(16) 0.02129(15) 0.02280(15) -0.00533(9) -0.00501(9) -0.00313(9) Cl1 0.0251(3) 0.0330(4) 0.0335(4) -0.0111(3) -0.0041(3) -0.0037(3) O1 0.0348(11) 0.0232(10) 0.0276(10) -0.0044(8) -0.0043(8) -0.0053(8) C1 0.0461(19) 0.0238(14) 0.0306(15) -0.0098(11) -0.0021(13) 0.0010(13) O2 0.0585(16) 0.0288(12) 0.0474(14) -0.0144(10) -0.0004(12) -0.0168(11) C2 0.0405(18) 0.0391(17) 0.0440(18) -0.0285(15) 0.0032(14) -0.0139(14) C3 0.0418(19) 0.057(2) 0.0385(17) -0.0296(16) -0.0181(15) 0.0081(16) C4 0.060(2) 0.0303(16) 0.0231(14) -0.0059(12) -0.0033(14) 0.0091(15) C5 0.0365(17) 0.0327(16) 0.0369(16) -0.0130(13) 0.0084(13) -0.0111(13) C6 0.0286(15) 0.0369(16) 0.0357(15) -0.0166(13) -0.0087(12) 0.0039(12) C7 0.0305(15) 0.0280(14) 0.0294(14) -0.0029(11) -0.0065(11) -0.0019(12) C8 0.0380(18) 0.0437(18) 0.0283(15) -0.0036(13) -0.0094(13) 0.0012(14) C9 0.0343(17) 0.058(2) 0.0268(15) -0.0144(14) -0.0077(13) -0.0024(15) C10 0.0314(16) 0.0419(18) 0.0344(16) -0.0175(13) -0.0035(13) -0.0070(13) C11 0.0227(13) 0.0315(15) 0.0316(14) -0.0116(11) -0.0034(11) -0.0064(11) C12 0.0292(15) 0.0271(14) 0.0322(14) -0.0084(11) 0.0014(11) -0.0066(11) N14 0.0247(12) 0.0280(12) 0.0242(11) -0.0065(9) -0.0047(9) -0.0037(9) _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 O1 2.075(2) . ? Ru1 N14 2.087(2) . ? Ru1 C6 2.160(3) . ? Ru1 C5 2.168(3) . ? Ru1 C1 2.178(3) . ? Ru1 C2 2.179(3) . ? Ru1 C4 2.190(3) . ? Ru1 C3 2.191(3) . ? Ru1 Cl1 2.4129(7) . ? O1 C12 1.290(4) . ? C1 C2 1.402(5) . ? C1 C6 1.415(5) . ? C1 H1 0.9500 . ? O2 C12 1.219(4) . ? C2 C3 1.421(6) . ? C2 H2 0.9500 . ? C3 C4 1.397(6) . ? C3 H3 0.9500 . ? C4 C5 1.418(5) . ? C4 H4 0.9500 . ? C5 C6 1.390(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N14 1.348(4) . ? C7 C8 1.392(4) . ? C7 H7 0.9500 . ? C8 C9 1.382(5) . ? C8 H8 0.9500 . ? C9 C10 1.389(5) . ? C9 H9 0.9500 . ? C10 C11 1.377(4) . ? C10 H10 0.9500 . ? C11 N14 1.346(4) . ? C11 C12 1.514(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 O1 Ru1 N14 77.54(9) . . ? O1 Ru1 C6 116.18(11) . . ? N14 Ru1 C6 94.57(11) . . ? O1 Ru1 C5 91.51(10) . . ? N14 Ru1 C5 117.95(12) . . ? C6 Ru1 C5 37.46(13) . . ? O1 Ru1 C1 153.89(12) . . ? N14 Ru1 C1 97.30(11) . . ? C6 Ru1 C1 38.07(13) . . ? C5 Ru1 C1 68.05(12) . . ? O1 Ru1 C2 158.40(12) . . ? N14 Ru1 C2 123.92(12) . . ? C6 Ru1 C2 68.33(13) . . ? C5 Ru1 C2 80.58(12) . . ? C1 Ru1 C2 37.54(14) . . ? O1 Ru1 C4 93.62(11) . . ? N14 Ru1 C4 154.93(13) . . ? C6 Ru1 C4 68.06(13) . . ? C5 Ru1 C4 37.98(14) . . ? C1 Ru1 C4 80.29(12) . . ? C2 Ru1 C4 67.82(14) . . ? O1 Ru1 C3 120.49(12) . . ? N14 Ru1 C3 161.68(14) . . ? C6 Ru1 C3 80.64(13) . . ? C5 Ru1 C3 68.00(14) . . ? C1 Ru1 C3 68.05(13) . . ? C2 Ru1 C3 37.94(15) . . ? C4 Ru1 C3 37.19(15) . . ? O1 Ru1 Cl1 87.04(6) . . ? N14 Ru1 Cl1 84.20(7) . . ? C6 Ru1 Cl1 156.01(9) . . ? C5 Ru1 Cl1 156.95(10) . . ? C1 Ru1 Cl1 118.19(10) . . ? C2 Ru1 Cl1 92.46(9) . . ? C4 Ru1 Cl1 119.11(11) . . ? C3 Ru1 Cl1 93.02(10) . . ? C12 O1 Ru1 118.09(18) . . ? C2 C1 C6 119.8(3) . . ? C2 C1 Ru1 71.27(19) . . ? C6 C1 Ru1 70.30(18) . . ? C2 C1 H1 120.1 . . ? C6 C1 H1 120.1 . . ? Ru1 C1 H1 131.0 . . ? C1 C2 C3 120.0(3) . . ? C1 C2 Ru1 71.19(18) . . ? C3 C2 Ru1 71.51(18) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? Ru1 C2 H2 129.8 . . ? C4 C3 C2 119.8(3) . . ? C4 C3 Ru1 71.34(19) . . ? C2 C3 Ru1 70.55(18) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? Ru1 C3 H3 130.6 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 Ru1 71.47(19) . . ? C5 C4 Ru1 70.19(18) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? Ru1 C4 H4 131.0 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 Ru1 70.97(18) . . ? C4 C5 Ru1 71.83(19) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? Ru1 C5 H5 129.8 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 Ru1 71.57(19) . . ? C1 C6 Ru1 71.63(18) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? Ru1 C6 H6 129.3 . . ? N14 C7 C8 121.4(3) . . ? N14 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C8 C7 119.3(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 119.1(3) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 118.6(3) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? N14 C11 C10 122.8(3) . . ? N14 C11 C12 114.6(3) . . ? C10 C11 C12 122.5(3) . . ? O2 C12 O1 125.4(3) . . ? O2 C12 C11 120.4(3) . . ? O1 C12 C11 114.3(2) . . ? C11 N14 C7 118.8(3) . . ? C11 N14 Ru1 115.29(19) . . ? C7 N14 Ru1 125.9(2) . . ? 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 N14 Ru1 O1 C12 4.1(2) . . . . ? C6 Ru1 O1 C12 -84.9(2) . . . . ? C5 Ru1 O1 C12 -114.3(2) . . . . ? C1 Ru1 O1 C12 -77.0(3) . . . . ? C2 Ru1 O1 C12 178.0(3) . . . . ? C4 Ru1 O1 C12 -152.2(2) . . . . ? C3 Ru1 O1 C12 -179.5(2) . . . . ? Cl1 Ru1 O1 C12 88.8(2) . . . . ? O1 Ru1 C1 C2 -144.3(2) . . . . ? N14 Ru1 C1 C2 139.2(2) . . . . ? C6 Ru1 C1 C2 -132.7(3) . . . . ? C5 Ru1 C1 C2 -103.6(2) . . . . ? C4 Ru1 C1 C2 -66.1(2) . . . . ? C3 Ru1 C1 C2 -29.4(2) . . . . ? Cl1 Ru1 C1 C2 51.9(2) . . . . ? O1 Ru1 C1 C6 -11.6(3) . . . . ? N14 Ru1 C1 C6 -88.10(19) . . . . ? C5 Ru1 C1 C6 29.15(19) . . . . ? C2 Ru1 C1 C6 132.7(3) . . . . ? C4 Ru1 C1 C6 66.7(2) . . . . ? C3 Ru1 C1 C6 103.3(2) . . . . ? Cl1 Ru1 C1 C6 -175.41(15) . . . . ? C6 C1 C2 C3 1.4(5) . . . . ? Ru1 C1 C2 C3 54.3(3) . . . . ? C6 C1 C2 Ru1 -52.8(3) . . . . ? O1 Ru1 C2 C1 135.8(3) . . . . ? N14 Ru1 C2 C1 -51.4(2) . . . . ? C6 Ru1 C2 C1 29.17(19) . . . . ? C5 Ru1 C2 C1 66.0(2) . . . . ? C4 Ru1 C2 C1 103.4(2) . . . . ? C3 Ru1 C2 C1 132.2(3) . . . . ? Cl1 Ru1 C2 C1 -136.06(18) . . . . ? O1 Ru1 C2 C3 3.6(4) . . . . ? N14 Ru1 C2 C3 176.43(19) . . . . ? C6 Ru1 C2 C3 -103.0(2) . . . . ? C5 Ru1 C2 C3 -66.1(2) . . . . ? C1 Ru1 C2 C3 -132.2(3) . . . . ? C4 Ru1 C2 C3 -28.8(2) . . . . ? Cl1 Ru1 C2 C3 91.8(2) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? Ru1 C2 C3 C4 53.6(3) . . . . ? C1 C2 C3 Ru1 -54.1(3) . . . . ? O1 Ru1 C3 C4 49.1(2) . . . . ? N14 Ru1 C3 C4 -141.9(3) . . . . ? C6 Ru1 C3 C4 -65.9(2) . . . . ? C5 Ru1 C3 C4 -29.1(2) . . . . ? C1 Ru1 C3 C4 -103.3(2) . . . . ? C2 Ru1 C3 C4 -132.4(3) . . . . ? Cl1 Ru1 C3 C4 137.43(19) . . . . ? O1 Ru1 C3 C2 -178.46(18) . . . . ? N14 Ru1 C3 C2 -9.5(5) . . . . ? C6 Ru1 C3 C2 66.6(2) . . . . ? C5 Ru1 C3 C2 103.4(2) . . . . ? C1 Ru1 C3 C2 29.1(2) . . . . ? C4 Ru1 C3 C2 132.4(3) . . . . ? Cl1 Ru1 C3 C2 -90.1(2) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? Ru1 C3 C4 C5 52.7(3) . . . . ? C2 C3 C4 Ru1 -53.3(3) . . . . ? O1 Ru1 C4 C3 -139.3(2) . . . . ? N14 Ru1 C4 C3 152.8(3) . . . . ? C6 Ru1 C4 C3 103.9(2) . . . . ? C5 Ru1 C4 C3 132.9(3) . . . . ? C1 Ru1 C4 C3 66.3(2) . . . . ? C2 Ru1 C4 C3 29.3(2) . . . . ? Cl1 Ru1 C4 C3 -50.6(2) . . . . ? O1 Ru1 C4 C5 87.82(19) . . . . ? N14 Ru1 C4 C5 19.9(4) . . . . ? C6 Ru1 C4 C5 -28.99(19) . . . . ? C1 Ru1 C4 C5 -66.6(2) . . . . ? C2 Ru1 C4 C5 -103.6(2) . . . . ? C3 Ru1 C4 C5 -132.9(3) . . . . ? Cl1 Ru1 C4 C5 176.44(15) . . . . ? C3 C4 C5 C6 0.7(5) . . . . ? Ru1 C4 C5 C6 54.0(3) . . . . ? C3 C4 C5 Ru1 -53.3(3) . . . . ? O1 Ru1 C5 C6 133.72(19) . . . . ? N14 Ru1 C5 C6 57.0(2) . . . . ? C1 Ru1 C5 C6 -29.59(19) . . . . ? C2 Ru1 C5 C6 -66.5(2) . . . . ? C4 Ru1 C5 C6 -132.3(3) . . . . ? C3 Ru1 C5 C6 -103.8(2) . . . . ? Cl1 Ru1 C5 C6 -140.3(2) . . . . ? O1 Ru1 C5 C4 -93.94(19) . . . . ? N14 Ru1 C5 C4 -170.62(18) . . . . ? C6 Ru1 C5 C4 132.3(3) . . . . ? C1 Ru1 C5 C4 102.7(2) . . . . ? C2 Ru1 C5 C4 65.8(2) . . . . ? C3 Ru1 C5 C4 28.5(2) . . . . ? Cl1 Ru1 C5 C4 -8.0(3) . . . . ? C4 C5 C6 C1 0.3(5) . . . . ? Ru1 C5 C6 C1 54.7(3) . . . . ? C4 C5 C6 Ru1 -54.4(3) . . . . ? C2 C1 C6 C5 -1.3(5) . . . . ? Ru1 C1 C6 C5 -54.6(3) . . . . ? C2 C1 C6 Ru1 53.3(3) . . . . ? O1 Ru1 C6 C5 -53.6(2) . . . . ? N14 Ru1 C6 C5 -131.96(19) . . . . ? C1 Ru1 C6 C5 132.0(3) . . . . ? C2 Ru1 C6 C5 103.2(2) . . . . ? C4 Ru1 C6 C5 29.4(2) . . . . ? C3 Ru1 C6 C5 65.9(2) . . . . ? Cl1 Ru1 C6 C5 142.0(2) . . . . ? O1 Ru1 C6 C1 174.35(17) . . . . ? N14 Ru1 C6 C1 96.00(19) . . . . ? C5 Ru1 C6 C1 -132.0(3) . . . . ? C2 Ru1 C6 C1 -28.80(19) . . . . ? C4 Ru1 C6 C1 -102.7(2) . . . . ? C3 Ru1 C6 C1 -66.2(2) . . . . ? Cl1 Ru1 C6 C1 10.0(3) . . . . ? N14 C7 C8 C9 0.4(5) . . . . ? C7 C8 C9 C10 0.6(5) . . . . ? C8 C9 C10 C11 -1.2(5) . . . . ? C9 C10 C11 N14 0.7(5) . . . . ? C9 C10 C11 C12 178.6(3) . . . . ? Ru1 O1 C12 O2 175.3(3) . . . . ? Ru1 O1 C12 C11 -4.9(3) . . . . ? N14 C11 C12 O2 -177.3(3) . . . . ? C10 C11 C12 O2 4.6(5) . . . . ? N14 C11 C12 O1 2.8(4) . . . . ? C10 C11 C12 O1 -175.3(3) . . . . ? C10 C11 N14 C7 0.3(4) . . . . ? C12 C11 N14 C7 -177.8(3) . . . . ? C10 C11 N14 Ru1 178.6(2) . . . . ? C12 C11 N14 Ru1 0.5(3) . . . . ? C8 C7 N14 C11 -0.9(5) . . . . ? C8 C7 N14 Ru1 -179.0(2) . . . . ? O1 Ru1 N14 C11 -2.3(2) . . . . ? C6 Ru1 N14 C11 113.6(2) . . . . ? C5 Ru1 N14 C11 82.8(2) . . . . ? C1 Ru1 N14 C11 151.7(2) . . . . ? C2 Ru1 N14 C11 -179.6(2) . . . . ? C4 Ru1 N14 C11 69.1(3) . . . . ? C3 Ru1 N14 C11 -172.6(3) . . . . ? Cl1 Ru1 N14 C11 -90.5(2) . . . . ? O1 Ru1 N14 C7 175.9(3) . . . . ? C6 Ru1 N14 C7 -68.3(3) . . . . ? C5 Ru1 N14 C7 -99.1(3) . . . . ? C1 Ru1 N14 C7 -30.1(3) . . . . ? C2 Ru1 N14 C7 -1.4(3) . . . . ? C4 Ru1 N14 C7 -112.8(3) . . . . ? C3 Ru1 N14 C7 5.6(5) . . . . ? Cl1 Ru1 N14 C7 87.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.625 _refine_diff_density_min -1.120 _refine_diff_density_rms 0.118