# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Xuetai Chen' _publ_contact_author_email XTCHEN@NETRA.NJU.EDU.CN _publ_section_title ; Synthesis, structures and catalytic activities of ruthenium (II) carbonyl chloride complexes containing pyridine-functionalised N-heterocyclic carbenes ; loop_ _publ_author_name 'Xuetai Chen' 'Yong Cheng' 'Yi-Zhi Li' 'Jia-Feng Sun' 'Hui-Jun Xu' ; Zi-Ling Xue ; # Attachment '1a,1b,1b,4b.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 714989' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 Cl2 N3 O2 Ru, 2(H2 O)' _chemical_formula_sum 'C14 H19 Cl2 N3 O4 Ru' _chemical_formula_weight 465.29 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 'P2(1)/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 11.732(2) _cell_length_b 8.9321(16) _cell_length_c 18.799(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.904(2) _cell_angle_gamma 90.00 _cell_volume 1951.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2682 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 24.53 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.79 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10192 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3821 _reflns_number_gt 2804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.05P)^2^+0.99P] 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 3821 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 C1 C 0.8142(4) -0.0202(6) -0.0479(2) 0.0518(11) Uani 1 1 d . . . H1 H 0.8695 0.0384 -0.0656 0.062 Uiso 1 1 calc R . . C2 C 0.7930(4) -0.1590(5) -0.0758(2) 0.0509(11) Uani 1 1 d . . . H2 H 0.8315 -0.1934 -0.1127 0.061 Uiso 1 1 calc R . . C3 C 0.7141(4) -0.2477(6) -0.0486(3) 0.0608(12) Uani 1 1 d . . . H3 H 0.6994 -0.3444 -0.0658 0.073 Uiso 1 1 calc R . . C4 C 0.6588(4) -0.1922(5) 0.0028(3) 0.0524(11) Uani 1 1 d . . . H4 H 0.6051 -0.2508 0.0220 0.063 Uiso 1 1 calc R . . C5 C 0.6808(4) -0.0484(5) 0.0277(2) 0.0451(10) Uani 1 1 d . . . C6 C 0.5459(4) -0.0386(6) 0.1190(3) 0.0525(12) Uani 1 1 d . . . H6 H 0.5123 -0.1327 0.1119 0.063 Uiso 1 1 calc R . . C7 C 0.5214(4) 0.0593(5) 0.1659(2) 0.0493(11) Uani 1 1 d . . . H7 H 0.4668 0.0498 0.1971 0.059 Uiso 1 1 calc R . . C8 C 0.6592(4) 0.1589(5) 0.1073(2) 0.0470(10) Uani 1 1 d . . . C9 C 0.5941(4) 0.3216(6) 0.2073(2) 0.0482(10) Uani 1 1 d . . . C10 C 0.7127(4) 0.3331(6) 0.2506(3) 0.0568(12) Uani 1 1 d . . . H10A H 0.7693 0.3446 0.2187 0.085 Uiso 1 1 calc R . . H10B H 0.7286 0.2438 0.2787 0.085 Uiso 1 1 calc R . . H10C H 0.7153 0.4182 0.2820 0.085 Uiso 1 1 calc R . . C11 C 0.5592(4) 0.4508(5) 0.1577(3) 0.0558(12) Uani 1 1 d . . . H11A H 0.5763 0.5433 0.1829 0.084 Uiso 1 1 calc R . . H11B H 0.4781 0.4453 0.1413 0.084 Uiso 1 1 calc R . . H11C H 0.6008 0.4462 0.1172 0.084 Uiso 1 1 calc R . . C12 C 0.5042(4) 0.2994(6) 0.2578(3) 0.0555(12) Uani 1 1 d . . . H12A H 0.5291 0.2218 0.2917 0.083 Uiso 1 1 calc R . . H12B H 0.4322 0.2715 0.2304 0.083 Uiso 1 1 calc R . . H12C H 0.4947 0.3911 0.2830 0.083 Uiso 1 1 calc R . . C13 C 0.8070(4) 0.4414(6) 0.0949(3) 0.0548(12) Uani 1 1 d . . . C14 C 0.9002(4) 0.3110(6) -0.0073(3) 0.0517(11) Uani 1 1 d . . . Cl1 Cl 0.63461(11) 0.34842(14) -0.03497(6) 0.0575(3) Uani 1 1 d . . . Ru1 Ru 0.78653(3) 0.25428(4) 0.051793(18) 0.04087(12) Uani 1 1 d . . . Cl2 Cl 0.93029(9) 0.14451(14) 0.13852(6) 0.0536(3) Uani 1 1 d . . . N1 N 0.7602(3) 0.0358(4) 0.0032(2) 0.0471(9) Uani 1 1 d . . . N2 N 0.6283(3) 0.0173(4) 0.08159(19) 0.0456(8) Uani 1 1 d . . . N3 N 0.5941(3) 0.1824(4) 0.15991(19) 0.0443(8) Uani 1 1 d . . . O1 O 0.8272(3) 0.5556(4) 0.12040(16) 0.0505(8) Uani 1 1 d . . . O2 O 0.9670(3) 0.3442(4) -0.04120(17) 0.0557(8) Uani 1 1 d . . . O3 O 0.3545(3) 0.8932(4) 0.27628(17) 0.0598(9) Uani 1 1 d . . . H3D H 0.3875 0.8280 0.2532 0.072 Uiso 1 1 d R . . H3B H 0.2914 0.9193 0.2517 0.072 Uiso 1 1 d R . . O4 O 0.2628(3) 0.6545(4) 0.19294(17) 0.0558(8) Uani 1 1 d . . . H4A H 0.1903 0.6537 0.1927 0.067 Uiso 1 1 d R . . H4B H 0.2778 0.6647 0.1503 0.067 Uiso 1 1 d 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 C1 0.045(3) 0.058(3) 0.053(3) -0.004(2) 0.009(2) -0.010(2) C2 0.048(3) 0.056(3) 0.050(3) -0.013(2) 0.010(2) 0.007(2) C3 0.049(3) 0.063(3) 0.068(3) -0.009(3) 0.003(2) 0.001(2) C4 0.049(3) 0.048(3) 0.060(3) 0.004(2) 0.007(2) -0.013(2) C5 0.042(2) 0.038(2) 0.052(3) 0.0089(19) -0.006(2) -0.0043(18) C6 0.045(3) 0.054(3) 0.056(3) 0.011(2) -0.002(2) -0.016(2) C7 0.041(2) 0.061(3) 0.046(2) 0.017(2) 0.006(2) -0.017(2) C8 0.044(2) 0.045(2) 0.050(2) 0.012(2) -0.002(2) -0.0079(19) C9 0.044(2) 0.057(3) 0.041(2) 0.004(2) -0.0027(19) -0.007(2) C10 0.053(3) 0.057(3) 0.054(3) 0.000(2) -0.012(2) -0.007(2) C11 0.056(3) 0.048(3) 0.058(3) 0.010(2) -0.010(2) -0.015(2) C12 0.053(3) 0.058(3) 0.055(3) -0.003(2) 0.006(2) -0.005(2) C13 0.058(3) 0.058(3) 0.050(3) -0.013(2) 0.010(2) -0.017(2) C14 0.053(3) 0.048(3) 0.053(3) 0.011(2) 0.003(2) -0.019(2) Cl1 0.0565(7) 0.0548(7) 0.0558(7) 0.0113(6) -0.0115(5) -0.0100(5) Ru1 0.03882(19) 0.04075(19) 0.04117(19) 0.00389(15) -0.00119(13) -0.01380(14) Cl2 0.0432(6) 0.0576(7) 0.0541(6) 0.0050(5) -0.0139(5) -0.0100(5) N1 0.049(2) 0.0374(19) 0.054(2) 0.0043(17) 0.0045(18) -0.0041(16) N2 0.0414(19) 0.050(2) 0.0437(18) 0.0049(17) -0.0014(15) -0.0079(16) N3 0.0407(19) 0.046(2) 0.044(2) 0.0049(17) -0.0015(15) -0.0042(16) O1 0.0508(18) 0.0523(19) 0.0494(18) -0.0121(15) 0.0100(15) -0.0136(15) O2 0.056(2) 0.059(2) 0.0547(19) -0.0057(17) 0.0149(17) -0.0179(16) O3 0.063(2) 0.059(2) 0.059(2) 0.0188(17) 0.0159(17) -0.0051(16) O4 0.059(2) 0.062(2) 0.0494(17) -0.0103(16) 0.0178(15) 0.0118(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.319(6) . ? C1 C2 1.356(7) . ? C1 H1 0.9300 . ? C2 C3 1.370(7) . ? C2 H2 0.9300 . ? C3 C4 1.331(7) . ? C3 H3 0.9300 . ? C4 C5 1.380(7) . ? C4 H4 0.9300 . ? C5 N1 1.329(5) . ? C5 N2 1.386(6) . ? C6 C7 1.303(7) . ? C6 N2 1.366(6) . ? C6 H6 0.9300 . ? C7 N3 1.406(5) . ? C7 H7 0.9300 . ? C8 N3 1.346(6) . ? C8 N2 1.384(6) . ? C8 Ru1 2.116(4) . ? C9 C11 1.505(6) . ? C9 C10 1.516(6) . ? C9 C12 1.526(6) . ? C9 N3 1.529(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O1 1.138(5) . ? C13 Ru1 1.859(5) . ? C14 O2 1.116(5) . ? C14 Ru1 1.917(5) . ? Cl1 Ru1 2.3968(12) . ? Ru1 N1 2.159(4) . ? Ru1 Cl2 2.3891(12) . ? O3 H3D 0.8499 . ? O3 H3B 0.8499 . ? O4 H4A 0.8500 . ? O4 H4B 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.2(4) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 118.8(4) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 118.5(5) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C4 C5 120.4(5) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 121.0(4) . . ? N1 C5 N2 114.7(4) . . ? C4 C5 N2 124.2(4) . . ? C7 C6 N2 109.9(4) . . ? C7 C6 H6 125.0 . . ? N2 C6 H6 125.0 . . ? C6 C7 N3 106.1(4) . . ? C6 C7 H7 127.0 . . ? N3 C7 H7 127.0 . . ? N3 C8 N2 104.6(4) . . ? N3 C8 Ru1 144.0(3) . . ? N2 C8 Ru1 111.4(3) . . ? C11 C9 C10 115.7(4) . . ? C11 C9 C12 109.4(4) . . ? C10 C9 C12 109.6(4) . . ? C11 C9 N3 106.5(3) . . ? C10 C9 N3 107.2(4) . . ? C12 C9 N3 108.2(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 Ru1 175.3(4) . . ? O2 C14 Ru1 179.4(4) . . ? C13 Ru1 C14 87.5(2) . . ? C13 Ru1 C8 101.8(2) . . ? C14 Ru1 C8 170.7(2) . . ? C13 Ru1 N1 178.82(18) . . ? C14 Ru1 N1 93.65(18) . . ? C8 Ru1 N1 77.01(16) . . ? C13 Ru1 Cl2 91.97(16) . . ? C14 Ru1 Cl2 91.25(15) . . ? C8 Ru1 Cl2 88.75(12) . . ? N1 Ru1 Cl2 87.97(10) . . ? C13 Ru1 Cl1 91.20(16) . . ? C14 Ru1 Cl1 91.40(15) . . ? C8 Ru1 Cl1 88.14(12) . . ? N1 Ru1 Cl1 88.81(10) . . ? Cl2 Ru1 Cl1 175.95(4) . . ? C1 N1 C5 117.9(4) . . ? C1 N1 Ru1 126.5(3) . . ? C5 N1 Ru1 115.5(3) . . ? C6 N2 C8 108.9(4) . . ? C6 N2 C5 129.6(4) . . ? C8 N2 C5 121.4(4) . . ? C8 N3 C7 110.4(4) . . ? C8 N3 C9 126.9(4) . . ? C7 N3 C9 122.7(4) . . ? H3D O3 H3B 109.5 . . ? H4A O4 H4B 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 N1 C1 C2 C3 -1.8(8) . . . . ? C1 C2 C3 C4 1.8(7) . . . . ? C2 C3 C4 C5 0.2(8) . . . . ? C3 C4 C5 N1 -2.5(7) . . . . ? C3 C4 C5 N2 -179.2(4) . . . . ? N2 C6 C7 N3 -1.8(5) . . . . ? N3 C8 Ru1 C13 -1.8(6) . . . . ? N2 C8 Ru1 C13 178.4(3) . . . . ? N3 C8 Ru1 N1 178.1(6) . . . . ? N2 C8 Ru1 N1 -1.7(3) . . . . ? N3 C8 Ru1 Cl2 89.9(5) . . . . ? N2 C8 Ru1 Cl2 -89.9(3) . . . . ? N3 C8 Ru1 Cl1 -92.7(5) . . . . ? N2 C8 Ru1 Cl1 87.5(3) . . . . ? C2 C1 N1 C5 -0.5(7) . . . . ? C2 C1 N1 Ru1 179.9(4) . . . . ? C4 C5 N1 C1 2.6(6) . . . . ? N2 C5 N1 C1 179.6(4) . . . . ? C4 C5 N1 Ru1 -177.7(3) . . . . ? N2 C5 N1 Ru1 -0.8(5) . . . . ? C14 Ru1 N1 C1 1.3(4) . . . . ? C8 Ru1 N1 C1 -179.0(4) . . . . ? Cl2 Ru1 N1 C1 -89.8(4) . . . . ? Cl1 Ru1 N1 C1 92.6(4) . . . . ? C14 Ru1 N1 C5 -178.3(3) . . . . ? C8 Ru1 N1 C5 1.4(3) . . . . ? Cl2 Ru1 N1 C5 90.5(3) . . . . ? Cl1 Ru1 N1 C5 -87.0(3) . . . . ? C7 C6 N2 C8 1.0(5) . . . . ? C7 C6 N2 C5 179.0(4) . . . . ? N3 C8 N2 C6 0.4(5) . . . . ? Ru1 C8 N2 C6 -179.8(3) . . . . ? N3 C8 N2 C5 -177.9(3) . . . . ? Ru1 C8 N2 C5 2.0(5) . . . . ? N1 C5 N2 C6 -178.7(4) . . . . ? C4 C5 N2 C6 -1.9(7) . . . . ? N1 C5 N2 C8 -0.9(6) . . . . ? C4 C5 N2 C8 176.0(4) . . . . ? N2 C8 N3 C7 -1.5(5) . . . . ? Ru1 C8 N3 C7 178.7(4) . . . . ? N2 C8 N3 C9 179.4(4) . . . . ? Ru1 C8 N3 C9 -0.4(8) . . . . ? C6 C7 N3 C8 2.1(5) . . . . ? C6 C7 N3 C9 -178.7(4) . . . . ? C10 C9 N3 C8 -63.4(5) . . . . ? C11 C9 N3 C8 61.0(5) . . . . ? C12 C9 N3 C8 178.5(4) . . . . ? C10 C9 N3 C7 117.6(4) . . . . ? C11 C9 N3 C7 -118.0(4) . . . . ? C12 C9 N3 C7 -0.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.383 _refine_diff_density_min -0.896 _refine_diff_density_rms 0.079 data_1b _database_code_depnum_ccdc_archive 'CCDC 714990' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 Cl2 N3 O2 Ru' _chemical_formula_sum 'C14 H15 Cl2 N3 O2 Ru' _chemical_formula_weight 429.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 14.312(12) _cell_length_b 6.517(6) _cell_length_c 17.998(15) _cell_angle_alpha 90.00 _cell_angle_beta 106.647(11) _cell_angle_gamma 90.00 _cell_volume 1608(2) _cell_formula_units_Z 4 _cell_measurement_temperature 275(2) _cell_measurement_reflns_used 2310 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 28.00 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.773 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.77 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 275(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7795 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3140 _reflns_number_gt 2363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement 'SADABS; Bruker, 2000' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.04P)^2^] 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 3140 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 C1 C 0.0586(3) 0.6477(7) 0.8167(2) 0.0312(9) Uani 1 1 d . . . H1 H 0.0892 0.6113 0.7795 0.037 Uiso 1 1 calc R . . C2 C -0.0364(3) 0.7093(7) 0.7923(2) 0.0327(9) Uani 1 1 d . . . H2 H -0.0712 0.7110 0.7400 0.039 Uiso 1 1 calc R . . C3 C -0.0792(3) 0.7703(6) 0.8500(2) 0.0301(9) Uani 1 1 d . . . H3 H -0.1430 0.8185 0.8362 0.036 Uiso 1 1 calc R . . C4 C -0.0273(3) 0.7589(6) 0.9257(3) 0.0305(9) Uani 1 1 d . . . H4 H -0.0554 0.7972 0.9642 0.037 Uiso 1 1 calc R . . C5 C 0.0667(3) 0.6905(6) 0.9448(2) 0.0263(8) Uani 1 1 d . . . C6 C 0.1066(3) 0.7335(6) 1.0875(2) 0.0306(8) Uani 1 1 d . . . H6 H 0.0494 0.7931 1.0918 0.037 Uiso 1 1 calc R . . C7 C 0.1866(3) 0.6900(7) 1.1449(3) 0.0347(9) Uani 1 1 d . . . H7 H 0.1953 0.7145 1.1973 0.042 Uiso 1 1 calc R . . C8 C 0.2184(3) 0.5882(6) 1.0368(2) 0.0269(8) Uani 1 1 d . . . C9 C 0.3544(3) 0.5243(7) 1.1609(2) 0.0340(9) Uani 1 1 d . . . C10 C 0.3633(3) 0.5667(7) 1.2470(2) 0.0383(10) Uani 1 1 d . . . H10A H 0.4240 0.5125 1.2788 0.057 Uiso 1 1 calc R . . H10B H 0.3102 0.5020 1.2605 0.057 Uiso 1 1 calc R . . H10C H 0.3613 0.7120 1.2551 0.057 Uiso 1 1 calc R . . C11 C 0.3586(3) 0.2929(7) 1.1479(2) 0.0348(10) Uani 1 1 d . . . H11A H 0.3427 0.2654 1.0933 0.052 Uiso 1 1 calc R . . H11B H 0.3125 0.2249 1.1691 0.052 Uiso 1 1 calc R . . H11C H 0.4230 0.2434 1.1731 0.052 Uiso 1 1 calc R . . C12 C 0.4278(3) 0.6525(7) 1.1367(2) 0.0386(10) Uani 1 1 d . . . H12A H 0.4238 0.6236 1.0836 0.058 Uiso 1 1 calc R . . H12B H 0.4921 0.6208 1.1690 0.058 Uiso 1 1 calc R . . H12C H 0.4143 0.7952 1.1420 0.058 Uiso 1 1 calc R . . C13 C 0.3703(3) 0.3674(6) 0.9754(2) 0.0287(8) Uani 1 1 d . . . C14 C 0.3156(3) 0.7481(6) 0.9350(2) 0.0287(8) Uani 1 1 d . . . Cl1 Cl 0.16207(6) 0.18320(14) 0.93513(5) 0.0268(2) Uani 1 1 d . . . Cl2 Cl 0.26599(7) 0.42925(18) 0.80873(5) 0.0328(2) Uani 1 1 d . . . N1 N 0.1097(2) 0.6370(5) 0.89133(17) 0.0223(6) Uani 1 1 d . . . N2 N 0.1264(2) 0.6719(5) 1.02082(17) 0.0223(6) Uani 1 1 d . . . N3 N 0.2545(2) 0.6024(5) 1.11323(16) 0.0265(7) Uani 1 1 d . . . O1 O 0.4427(2) 0.2907(5) 0.99531(18) 0.0403(7) Uani 1 1 d . . . O2 O 0.3564(2) 0.8923(5) 0.92955(17) 0.0428(7) Uani 1 1 d . . . Ru1 Ru 0.25043(2) 0.50351(5) 0.937006(16) 0.02293(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0290(19) 0.041(2) 0.0188(18) 0.0011(16) -0.0010(15) -0.0012(17) C2 0.031(2) 0.039(2) 0.0228(19) -0.0032(16) 0.0001(16) 0.0001(18) C3 0.0254(19) 0.030(2) 0.032(2) 0.0062(16) 0.0036(16) 0.0054(16) C4 0.0266(19) 0.0171(18) 0.044(2) 0.0024(16) 0.0036(17) -0.0007(15) C5 0.0283(19) 0.0271(18) 0.0211(19) -0.0021(15) 0.0031(15) 0.0037(16) C6 0.036(2) 0.030(2) 0.026(2) -0.0040(16) 0.0077(17) 0.0029(16) C7 0.034(2) 0.032(2) 0.038(2) -0.0152(18) 0.0099(18) 0.0027(17) C8 0.0304(19) 0.030(2) 0.0187(16) -0.0020(15) 0.0036(15) 0.0051(16) C9 0.0262(19) 0.044(2) 0.028(2) 0.0091(18) 0.0024(16) 0.0022(18) C10 0.028(2) 0.043(2) 0.036(2) -0.0079(19) -0.0033(18) 0.0143(18) C11 0.025(2) 0.042(2) 0.030(2) 0.0043(18) -0.0051(17) 0.0064(17) C12 0.034(2) 0.042(2) 0.031(2) 0.0038(19) -0.0048(18) -0.0111(19) C13 0.0245(19) 0.039(2) 0.0229(19) 0.0032(16) 0.0072(15) 0.0040(17) C14 0.0231(18) 0.033(2) 0.027(2) -0.0016(16) 0.0037(15) -0.0019(16) Cl1 0.0225(4) 0.0288(5) 0.0266(4) -0.0028(4) 0.0032(3) -0.0025(4) Cl2 0.0278(4) 0.0490(6) 0.0182(4) -0.0067(4) 0.0012(3) 0.0000(4) N1 0.0243(15) 0.0228(16) 0.0192(15) 0.0024(12) 0.0050(12) -0.0028(12) N2 0.0275(15) 0.0204(15) 0.0194(15) 0.0033(11) 0.0074(12) 0.0015(12) N3 0.0288(16) 0.0352(19) 0.0128(15) -0.0061(13) 0.0017(13) 0.0037(14) O1 0.0243(15) 0.0455(18) 0.0444(17) -0.0034(15) -0.0011(13) 0.0045(14) O2 0.0300(15) 0.049(2) 0.0396(17) 0.0063(15) -0.0051(13) -0.0084(15) Ru1 0.02229(15) 0.02767(17) 0.01668(15) -0.00170(12) 0.00216(10) 0.00010(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 C1 N1 1.335(5) . ? C1 C2 1.363(6) . ? C1 H1 0.9300 . ? C2 C3 1.406(6) . ? C2 H2 0.9300 . ? C3 C4 1.353(6) . ? C3 H3 0.9300 . ? C4 C5 1.364(5) . ? C4 H4 0.9300 . ? C5 N1 1.328(5) . ? C5 N2 1.396(5) . ? C6 C7 1.335(6) . ? C6 N2 1.370(5) . ? C6 H6 0.9300 . ? C7 N3 1.383(5) . ? C7 H7 0.9300 . ? C8 N3 1.328(5) . ? C8 N2 1.377(5) . ? C8 Ru1 2.052(4) . ? C9 C12 1.501(6) . ? C9 N3 1.529(5) . ? C9 C11 1.530(6) . ? C9 C10 1.542(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O1 1.113(5) . ? C13 Ru1 1.879(4) . ? C14 O2 1.126(5) . ? C14 Ru1 1.852(4) . ? Cl1 Ru1 2.436(2) . ? Cl2 Ru1 2.431(2) . ? N1 Ru1 2.131(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 123.2(4) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 116.7(4) . . ? C1 C2 H2 121.6 . . ? C3 C2 H2 121.6 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.3(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 122.1(4) . . ? N1 C5 N2 114.0(3) . . ? C4 C5 N2 123.9(4) . . ? C7 C6 N2 105.6(4) . . ? C7 C6 H6 127.2 . . ? N2 C6 H6 127.2 . . ? C6 C7 N3 108.5(4) . . ? C6 C7 H7 125.7 . . ? N3 C7 H7 125.7 . . ? N3 C8 N2 104.7(3) . . ? N3 C8 Ru1 143.9(3) . . ? N2 C8 Ru1 111.3(2) . . ? C12 C9 N3 105.7(3) . . ? C12 C9 C11 116.3(4) . . ? N3 C9 C11 108.2(3) . . ? C12 C9 C10 109.2(4) . . ? N3 C9 C10 107.4(3) . . ? C11 C9 C10 109.6(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 Ru1 176.7(4) . . ? O2 C14 Ru1 175.5(4) . . ? C5 N1 C1 118.8(3) . . ? C5 N1 Ru1 114.2(2) . . ? C1 N1 Ru1 126.5(3) . . ? C6 N2 C8 111.0(3) . . ? C6 N2 C5 127.7(3) . . ? C8 N2 C5 121.3(3) . . ? C8 N3 C7 110.2(3) . . ? C8 N3 C9 125.6(3) . . ? C7 N3 C9 124.1(3) . . ? C14 Ru1 C13 90.09(18) . . ? C14 Ru1 C8 91.47(17) . . ? C13 Ru1 C8 102.41(16) . . ? C14 Ru1 N1 93.82(15) . . ? C13 Ru1 N1 175.90(16) . . ? C8 Ru1 N1 78.72(13) . . ? C14 Ru1 Cl2 88.23(13) . . ? C13 Ru1 Cl2 86.12(12) . . ? C8 Ru1 Cl2 171.46(11) . . ? N1 Ru1 Cl2 92.78(9) . . ? C14 Ru1 Cl1 178.12(12) . . ? C13 Ru1 Cl1 90.94(14) . . ? C8 Ru1 Cl1 89.84(12) . . ? N1 Ru1 Cl1 85.12(10) . . ? Cl2 Ru1 Cl1 90.27(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 2.3(6) . . . . ? C1 C2 C3 C4 -2.4(6) . . . . ? C2 C3 C4 C5 0.9(6) . . . . ? C3 C4 C5 N1 0.9(6) . . . . ? C3 C4 C5 N2 -179.7(4) . . . . ? N2 C6 C7 N3 -0.1(5) . . . . ? C4 C5 N1 C1 -1.1(6) . . . . ? N2 C5 N1 C1 179.5(3) . . . . ? C4 C5 N1 Ru1 -173.3(3) . . . . ? N2 C5 N1 Ru1 7.3(4) . . . . ? C2 C1 N1 C5 -0.6(6) . . . . ? C2 C1 N1 Ru1 170.6(3) . . . . ? C7 C6 N2 C8 0.6(5) . . . . ? C7 C6 N2 C5 -177.9(4) . . . . ? N3 C8 N2 C6 -1.0(4) . . . . ? Ru1 C8 N2 C6 -178.2(3) . . . . ? N3 C8 N2 C5 177.7(3) . . . . ? Ru1 C8 N2 C5 0.4(5) . . . . ? N1 C5 N2 C6 173.1(3) . . . . ? C4 C5 N2 C6 -6.3(6) . . . . ? N1 C5 N2 C8 -5.3(5) . . . . ? C4 C5 N2 C8 175.3(4) . . . . ? N2 C8 N3 C7 0.9(5) . . . . ? Ru1 C8 N3 C7 176.6(4) . . . . ? N2 C8 N3 C9 178.0(4) . . . . ? Ru1 C8 N3 C9 -6.3(8) . . . . ? C6 C7 N3 C8 -0.5(5) . . . . ? C6 C7 N3 C9 -177.7(4) . . . . ? C12 C9 N3 C8 65.6(5) . . . . ? C11 C9 N3 C8 -59.7(5) . . . . ? C10 C9 N3 C8 -177.9(4) . . . . ? C12 C9 N3 C7 -117.7(4) . . . . ? C11 C9 N3 C7 117.0(4) . . . . ? C10 C9 N3 C7 -1.2(5) . . . . ? N3 C8 Ru1 C14 -79.3(5) . . . . ? N2 C8 Ru1 C14 96.3(3) . . . . ? N3 C8 Ru1 C13 11.1(6) . . . . ? N2 C8 Ru1 C13 -173.3(3) . . . . ? N3 C8 Ru1 N1 -172.9(5) . . . . ? N3 C8 Ru1 Cl1 102.1(5) . . . . ? N2 C8 Ru1 Cl1 -82.4(3) . . . . ? C5 N1 Ru1 C14 -96.4(3) . . . . ? C5 N1 Ru1 C8 -5.6(3) . . . . ? C1 N1 Ru1 C8 -177.2(3) . . . . ? C5 N1 Ru1 Cl2 175.2(3) . . . . ? C1 N1 Ru1 Cl2 3.7(3) . . . . ? C5 N1 Ru1 Cl1 85.2(3) . . . . ? C1 N1 Ru1 Cl1 -86.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.456 _refine_diff_density_min -1.024 _refine_diff_density_rms 0.104 data_2b _database_code_depnum_ccdc_archive 'CCDC 714991' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 Cl2 N3 O2 Ru' _chemical_formula_weight 429.26 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 ? _symmetry_space_group_name_H-M ? 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 14.7065(12) _cell_length_b 9.6796(7) _cell_length_c 12.6558(11) _cell_angle_alpha 90.00 _cell_angle_beta 115.0470(10) _cell_angle_gamma 90.00 _cell_volume 1632.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.296 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8525 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3198 _reflns_number_gt 2607 _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^)+(0.0606P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3198 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 C8 C 0.1944(3) 0.1573(4) 0.2647(4) 0.0339(9) Uani 1 1 d . . . C7 C 0.1617(3) -0.0679(4) 0.2176(4) 0.0322(9) Uani 1 1 d . . . H7 H 0.1716 -0.1625 0.2154 0.039 Uiso 1 1 calc R . . C6 C 0.0768(3) -0.0009(4) 0.1591(4) 0.0339(9) Uani 1 1 d . . . H6 H 0.0158 -0.0397 0.1091 0.041 Uiso 1 1 calc R . . C5 C 0.0324(3) 0.2510(5) 0.1446(4) 0.0320(8) Uani 1 1 d . . . C4 C -0.0676(3) 0.2391(5) 0.0707(4) 0.0380(10) Uani 1 1 d . . . H4 H -0.0973 0.1531 0.0459 0.046 Uiso 1 1 calc R . . C3 C -0.1224(3) 0.3591(5) 0.0346(4) 0.0385(10) Uani 1 1 d . . . H3 H -0.1900 0.3553 -0.0168 0.046 Uiso 1 1 calc R . . C2 C -0.0769(3) 0.4848(5) 0.0748(4) 0.0393(10) Uani 1 1 d . . . H2 H -0.1133 0.5664 0.0511 0.047 Uiso 1 1 calc R . . C1 C 0.0232(3) 0.4874(4) 0.1506(4) 0.0377(10) Uani 1 1 d . . . H1 H 0.0536 0.5721 0.1789 0.045 Uiso 1 1 calc R . . C9 C 0.3382(3) -0.0094(5) 0.3601(4) 0.0341(9) Uani 1 1 d . . . H9A H 0.3404 -0.1067 0.3795 0.041 Uiso 1 1 calc R . . H9B H 0.3600 0.0428 0.4320 0.041 Uiso 1 1 calc R . . C10 C 0.4101(3) 0.0173(5) 0.3046(4) 0.0381(10) Uani 1 1 d . . . H10A H 0.4122 0.1162 0.2935 0.046 Uiso 1 1 calc R . . H10B H 0.4766 -0.0106 0.3599 0.046 Uiso 1 1 calc R . . C11 C 0.3888(3) -0.0517(5) 0.1908(4) 0.0398(10) Uani 1 1 d . . . H11A H 0.3199 -0.0322 0.1372 0.048 Uiso 1 1 calc R . . H11B H 0.4317 -0.0107 0.1584 0.048 Uiso 1 1 calc R . . C12 C 0.4036(3) -0.2018(5) 0.1964(4) 0.0383(10) Uani 1 1 d . . . H12A H 0.4664 -0.2241 0.2605 0.057 Uiso 1 1 calc R . . H12B H 0.4044 -0.2337 0.1250 0.057 Uiso 1 1 calc R . . H12C H 0.3498 -0.2459 0.2075 0.057 Uiso 1 1 calc R . . C13 C 0.3605(3) 0.3260(5) 0.4281(4) 0.0430(11) Uani 1 1 d . . . C14 C 0.2859(3) 0.3816(5) 0.2030(4) 0.0377(10) Uani 1 1 d . . . Cl2 Cl 0.24913(8) 0.60455(11) 0.34659(9) 0.0352(2) Uani 1 1 d . . . Cl1 Cl 0.16399(8) 0.33601(10) 0.45595(9) 0.0323(2) Uani 1 1 d . . . N3 N 0.2337(3) 0.0290(4) 0.2832(3) 0.0324(8) Uani 1 1 d . . . N2 N 0.0957(3) 0.1377(3) 0.1861(3) 0.0331(8) Uani 1 1 d . . . N1 N 0.0782(3) 0.3726(4) 0.1847(3) 0.0309(7) Uani 1 1 d . . . O1 O 0.4387(2) 0.3113(3) 0.4997(3) 0.0437(8) Uani 1 1 d . . . O2 O 0.3209(2) 0.4049(3) 0.1399(3) 0.0369(7) Uani 1 1 d . . . Ru1 Ru 0.23213(3) 0.35546(4) 0.31123(3) 0.03396(14) 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 C8 0.035(2) 0.036(2) 0.034(2) 0.0042(18) 0.0178(18) 0.0036(17) C7 0.032(2) 0.028(2) 0.034(2) -0.0032(17) 0.0118(17) -0.0004(16) C6 0.031(2) 0.032(2) 0.033(2) -0.0037(17) 0.0075(16) -0.0079(17) C5 0.034(2) 0.032(2) 0.031(2) 0.0033(17) 0.0152(17) -0.0001(17) C4 0.027(2) 0.046(3) 0.040(2) -0.011(2) 0.0136(17) -0.0059(18) C3 0.025(2) 0.052(3) 0.032(2) -0.0004(19) 0.0060(17) -0.0039(17) C2 0.031(2) 0.045(3) 0.037(2) 0.003(2) 0.0105(18) 0.0048(18) C1 0.036(2) 0.026(2) 0.038(2) -0.0026(17) 0.0039(18) -0.0024(17) C9 0.030(2) 0.041(2) 0.030(2) 0.0059(18) 0.0122(17) 0.0135(18) C10 0.030(2) 0.039(2) 0.044(2) 0.014(2) 0.0137(18) 0.0153(18) C11 0.033(2) 0.041(2) 0.041(2) 0.012(2) 0.0117(19) 0.0156(19) C12 0.034(2) 0.043(2) 0.038(2) 0.0114(19) 0.0152(18) 0.0181(19) C13 0.029(2) 0.049(3) 0.047(3) -0.002(2) 0.013(2) -0.0019(19) C14 0.043(2) 0.039(2) 0.031(2) 0.0000(19) 0.016(2) 0.001(2) Cl2 0.0358(5) 0.0340(5) 0.0340(5) 0.0000(4) 0.0131(4) -0.0015(4) Cl1 0.0312(5) 0.0323(5) 0.0347(5) -0.0005(4) 0.0152(4) 0.0013(4) N3 0.0338(18) 0.0305(18) 0.0351(19) 0.0008(14) 0.0167(15) 0.0026(14) N2 0.0281(17) 0.0310(18) 0.040(2) -0.0027(15) 0.0142(15) -0.0019(14) N1 0.0306(18) 0.0349(19) 0.0334(18) 0.0012(15) 0.0196(15) 0.0055(14) O1 0.0402(18) 0.0366(16) 0.0405(17) -0.0082(13) 0.0037(14) 0.0038(14) O2 0.0358(15) 0.0404(16) 0.0368(16) 0.0012(13) 0.0177(13) -0.0126(13) Ru1 0.0340(2) 0.0361(2) 0.0328(2) -0.00053(14) 0.01518(16) 0.00125(13) _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 C8 N3 1.348(5) . ? C8 N2 1.382(6) . ? C8 Ru1 2.014(4) . ? C7 C6 1.320(6) . ? C7 N3 1.395(5) . ? C7 H7 0.9300 . ? C6 N2 1.383(5) . ? C6 H6 0.9300 . ? C5 N1 1.344(6) . ? C5 C4 1.374(6) . ? C5 N2 1.389(6) . ? C4 C3 1.376(7) . ? C4 H4 0.9300 . ? C3 C2 1.378(7) . ? C3 H3 0.9300 . ? C2 C1 1.376(6) . ? C2 H2 0.9300 . ? C1 N1 1.334(5) . ? C1 H1 0.9300 . ? C9 N3 1.477(5) . ? C9 C10 1.518(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.496(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.467(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O1 1.132(5) . ? C13 Ru1 1.863(5) . ? C14 O2 1.141(5) . ? C14 Ru1 1.866(5) . ? Cl2 Ru1 2.4458(11) . ? Cl1 Ru1 2.4388(11) . ? N1 Ru1 2.156(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C8 N2 103.9(4) . . ? N3 C8 Ru1 141.4(3) . . ? N2 C8 Ru1 114.6(3) . . ? C6 C7 N3 107.6(4) . . ? C6 C7 H7 126.2 . . ? N3 C7 H7 126.2 . . ? C7 C6 N2 107.2(4) . . ? C7 C6 H6 126.4 . . ? N2 C6 H6 126.4 . . ? N1 C5 C4 123.4(4) . . ? N1 C5 N2 113.6(4) . . ? C4 C5 N2 122.9(4) . . ? C5 C4 C3 117.6(4) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C1 C2 C3 118.8(4) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? N1 C1 C2 122.2(4) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? N3 C9 C10 112.8(3) . . ? N3 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N3 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 117.8(4) . . ? C11 C10 H10A 107.8 . . ? C9 C10 H10A 107.8 . . ? C11 C10 H10B 107.8 . . ? C9 C10 H10B 107.8 . . ? H10A C10 H10B 107.2 . . ? C12 C11 C10 115.4(4) . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C10 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 Ru1 178.4(4) . . ? O2 C14 Ru1 176.0(4) . . ? C8 N3 C7 110.8(3) . . ? C8 N3 C9 126.6(4) . . ? C7 N3 C9 122.6(3) . . ? C8 N2 C6 110.5(3) . . ? C8 N2 C5 119.6(3) . . ? C6 N2 C5 129.8(4) . . ? C1 N1 C5 118.0(4) . . ? C1 N1 Ru1 127.3(3) . . ? C5 N1 Ru1 114.4(3) . . ? C13 Ru1 C14 90.1(2) . . ? C13 Ru1 C8 98.5(2) . . ? C14 Ru1 C8 93.70(19) . . ? C13 Ru1 N1 173.92(18) . . ? C14 Ru1 N1 94.72(16) . . ? C8 Ru1 N1 77.49(15) . . ? C13 Ru1 Cl1 89.58(16) . . ? C14 Ru1 Cl1 176.52(15) . . ? C8 Ru1 Cl1 89.78(13) . . ? N1 Ru1 Cl1 85.86(9) . . ? C13 Ru1 Cl2 90.84(16) . . ? C14 Ru1 Cl2 87.61(15) . . ? C8 Ru1 Cl2 170.55(13) . . ? N1 Ru1 Cl2 93.08(9) . . ? Cl1 Ru1 Cl2 88.93(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C7 C6 N2 1.1(5) . . . . ? N1 C5 C4 C3 1.5(7) . . . . ? N2 C5 C4 C3 -179.4(4) . . . . ? C5 C4 C3 C2 -1.4(7) . . . . ? C4 C3 C2 C1 0.2(7) . . . . ? C3 C2 C1 N1 1.3(7) . . . . ? N3 C9 C10 C11 -57.6(5) . . . . ? C9 C10 C11 C12 -70.0(5) . . . . ? N2 C8 N3 C7 0.3(5) . . . . ? Ru1 C8 N3 C7 -178.9(4) . . . . ? N2 C8 N3 C9 179.5(4) . . . . ? Ru1 C8 N3 C9 0.2(8) . . . . ? C6 C7 N3 C8 -0.9(5) . . . . ? C6 C7 N3 C9 179.9(4) . . . . ? C10 C9 N3 C8 -79.3(5) . . . . ? C10 C9 N3 C7 99.8(5) . . . . ? N3 C8 N2 C6 0.3(5) . . . . ? Ru1 C8 N2 C6 179.8(3) . . . . ? N3 C8 N2 C5 -178.3(4) . . . . ? Ru1 C8 N2 C5 1.2(5) . . . . ? C7 C6 N2 C8 -0.9(5) . . . . ? C7 C6 N2 C5 177.6(4) . . . . ? N1 C5 N2 C8 2.4(6) . . . . ? C4 C5 N2 C8 -176.9(4) . . . . ? N1 C5 N2 C6 -176.0(4) . . . . ? C4 C5 N2 C6 4.8(7) . . . . ? C2 C1 N1 C5 -1.3(7) . . . . ? C2 C1 N1 Ru1 -175.3(3) . . . . ? C4 C5 N1 C1 -0.1(7) . . . . ? N2 C5 N1 C1 -179.3(4) . . . . ? C4 C5 N1 Ru1 174.7(4) . . . . ? N2 C5 N1 Ru1 -4.5(4) . . . . ? O1 C13 Ru1 C14 93(18) . . . . ? O1 C13 Ru1 C8 -173(100) . . . . ? O1 C13 Ru1 N1 -125(17) . . . . ? O1 C13 Ru1 Cl1 -83(18) . . . . ? O1 C13 Ru1 Cl2 6(18) . . . . ? O2 C14 Ru1 C13 -72(6) . . . . ? O2 C14 Ru1 C8 -171(6) . . . . ? O2 C14 Ru1 N1 111(6) . . . . ? O2 C14 Ru1 Cl1 12(8) . . . . ? O2 C14 Ru1 Cl2 19(6) . . . . ? N3 C8 Ru1 C13 -8.1(5) . . . . ? N2 C8 Ru1 C13 172.7(3) . . . . ? N3 C8 Ru1 C14 82.5(5) . . . . ? N2 C8 Ru1 C14 -96.7(3) . . . . ? N3 C8 Ru1 N1 176.5(5) . . . . ? N2 C8 Ru1 N1 -2.7(3) . . . . ? N3 C8 Ru1 Cl1 -97.6(5) . . . . ? N2 C8 Ru1 Cl1 83.1(3) . . . . ? N3 C8 Ru1 Cl2 -179.8(4) . . . . ? N2 C8 Ru1 Cl2 1.0(10) . . . . ? C1 N1 Ru1 C13 129.0(17) . . . . ? C5 N1 Ru1 C13 -45.2(18) . . . . ? C1 N1 Ru1 C14 -89.0(4) . . . . ? C5 N1 Ru1 C14 96.8(3) . . . . ? C1 N1 Ru1 C8 178.2(4) . . . . ? C5 N1 Ru1 C8 4.1(3) . . . . ? C1 N1 Ru1 Cl1 87.5(4) . . . . ? C5 N1 Ru1 Cl1 -86.6(3) . . . . ? C1 N1 Ru1 Cl2 -1.2(4) . . . . ? C5 N1 Ru1 Cl2 -175.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.479 _refine_diff_density_min -0.884 _refine_diff_density_rms 0.100 data_4b _database_code_depnum_ccdc_archive 'CCDC 714992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 Cl2 N3 O2 Ru' _chemical_formula_sum 'C15 H17 Cl2 N3 O2 Ru' _chemical_formula_weight 443.29 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 'P2(1)/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 7.7333(16) _cell_length_b 17.937(4) _cell_length_c 12.653(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.690(3) _cell_angle_gamma 90.00 _cell_volume 1751.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4175 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.81 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.79 _exptl_absorpt_process_details 'SADABS; Bruker,2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9321 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3436 _reflns_number_gt 2611 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.04P)^2^] 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 3436 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 C1 C 0.2617(6) -0.0684(2) 0.8930(3) 0.0342(9) Uani 1 1 d . . . H1 H 0.1415 -0.0699 0.8933 0.041 Uiso 1 1 calc R . . C2 C 0.3597(6) -0.1135(2) 0.9642(3) 0.0381(10) Uani 1 1 d . . . H2 H 0.3077 -0.1459 1.0100 0.046 Uiso 1 1 calc R . . C3 C 0.5382(6) -0.1076(3) 0.9631(3) 0.0442(11) Uani 1 1 d . . . H3 H 0.6082 -0.1366 1.0095 0.053 Uiso 1 1 calc R . . C4 C 0.6132(5) -0.0602(2) 0.8956(3) 0.0362(9) Uani 1 1 d . . . H4 H 0.7333 -0.0567 0.8963 0.043 Uiso 1 1 calc R . . C5 C 0.5092(5) -0.0169(2) 0.8252(3) 0.0340(9) Uani 1 1 d . . . C6 C 0.5866(6) 0.0335(2) 0.7493(3) 0.0384(9) Uani 1 1 d . . . H6A H 0.7111 0.0357 0.7644 0.046 Uiso 1 1 calc R . . H6B H 0.5644 0.0145 0.6779 0.046 Uiso 1 1 calc R . . C7 C 0.6094(6) 0.1734(2) 0.7758(3) 0.0379(10) Uani 1 1 d . . . H7 H 0.7294 0.1767 0.7854 0.046 Uiso 1 1 calc R . . C8 C 0.4984(6) 0.2291(2) 0.7777(3) 0.0404(10) Uani 1 1 d . . . H8 H 0.5257 0.2791 0.7892 0.048 Uiso 1 1 calc R . . C9 C 0.3428(5) 0.1238(2) 0.7450(3) 0.0320(9) Uani 1 1 d . . . C10 C 0.1761(6) 0.2446(2) 0.7598(3) 0.0365(9) Uani 1 1 d . . . H10A H 0.0760 0.2149 0.7365 0.044 Uiso 1 1 calc R . . H10B H 0.1843 0.2859 0.7109 0.044 Uiso 1 1 calc R . . C11 C 0.1530(6) 0.2749(3) 0.8725(3) 0.0470(11) Uani 1 1 d . . . H11A H 0.1553 0.2342 0.9231 0.056 Uiso 1 1 calc R . . H11B H 0.2460 0.3092 0.8933 0.056 Uiso 1 1 calc R . . C12 C -0.0237(6) 0.3156(3) 0.8706(4) 0.0480(12) Uani 1 1 d . . . H12A H -0.0116 0.3654 0.8420 0.058 Uiso 1 1 calc R . . H12B H -0.1078 0.2888 0.8247 0.058 Uiso 1 1 calc R . . C13 C -0.0892(6) 0.3207(3) 0.9832(3) 0.0422(10) Uani 1 1 d . . . H13A H -0.1104 0.2715 1.0091 0.063 Uiso 1 1 calc R . . H13B H -0.1947 0.3491 0.9810 0.063 Uiso 1 1 calc R . . H13C H -0.0032 0.3449 1.0294 0.063 Uiso 1 1 calc R . . C14 C 0.0109(5) 0.1004(2) 0.6323(3) 0.0315(8) Uani 1 1 d . . . C15 C 0.2618(5) 0.0084(2) 0.5957(3) 0.0326(9) Uani 1 1 d . . . Cl1 Cl 0.02017(13) 0.08149(5) 0.87504(7) 0.0346(2) Uani 1 1 d . . . Cl2 Cl -0.03469(13) -0.06629(5) 0.69485(7) 0.0310(2) Uani 1 1 d . . . Ru1 Ru 0.16330(4) 0.042480(17) 0.71838(2) 0.03092(11) Uani 1 1 d . . . N1 N 0.3341(4) -0.02334(18) 0.8246(3) 0.0336(7) Uani 1 1 d . . . N2 N 0.5128(4) 0.10880(18) 0.7566(2) 0.0319(7) Uani 1 1 d . . . N3 N 0.3320(4) 0.19926(19) 0.7592(3) 0.0329(7) Uani 1 1 d . . . O1 O -0.0792(4) 0.13629(16) 0.5802(2) 0.0408(7) Uani 1 1 d . . . O2 O 0.3127(4) -0.01332(18) 0.5217(2) 0.0458(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(2) 0.032(2) 0.035(2) 0.0021(16) 0.0042(17) -0.0003(17) C2 0.048(3) 0.031(2) 0.036(2) 0.0032(16) 0.0057(19) 0.0030(18) C3 0.049(3) 0.049(3) 0.034(2) 0.005(2) -0.004(2) 0.009(2) C4 0.034(2) 0.035(2) 0.040(2) -0.0053(17) 0.0012(17) 0.0144(19) C5 0.036(2) 0.033(2) 0.033(2) -0.0106(16) 0.0032(17) 0.0048(18) C6 0.034(2) 0.041(2) 0.041(2) -0.0023(18) 0.0088(18) 0.0018(19) C7 0.042(2) 0.037(2) 0.035(2) 0.0017(16) 0.0053(18) -0.011(2) C8 0.043(3) 0.034(2) 0.045(2) -0.0026(18) 0.008(2) -0.0136(19) C9 0.034(2) 0.033(2) 0.031(2) -0.0007(15) 0.0136(17) -0.0031(17) C10 0.042(2) 0.030(2) 0.038(2) -0.0081(16) 0.0002(18) 0.0074(18) C11 0.044(3) 0.053(3) 0.043(2) -0.009(2) -0.003(2) 0.020(2) C12 0.045(3) 0.055(3) 0.045(2) -0.030(2) 0.015(2) 0.012(2) C13 0.040(2) 0.051(3) 0.036(2) 0.0010(19) 0.0077(19) 0.020(2) C14 0.026(2) 0.0335(19) 0.0344(19) 0.0013(17) -0.0022(16) -0.0039(17) C15 0.034(2) 0.033(2) 0.032(2) -0.0045(16) 0.0064(17) -0.0028(18) Cl1 0.0356(5) 0.0363(5) 0.0325(5) -0.0004(4) 0.0056(4) 0.0003(4) Cl2 0.0295(5) 0.0297(4) 0.0340(5) -0.0007(4) 0.0041(4) 0.0001(4) Ru1 0.02920(18) 0.03207(18) 0.03179(18) -0.00034(13) 0.00439(12) 0.00026(14) N1 0.0353(19) 0.0330(17) 0.0329(17) 0.0010(14) 0.0060(14) 0.0042(15) N2 0.0340(19) 0.0295(16) 0.0329(17) 0.0052(13) 0.0063(14) 0.0025(14) N3 0.0290(17) 0.0366(17) 0.0332(17) -0.0029(14) 0.0027(14) 0.0000(15) O1 0.0335(15) 0.0380(16) 0.0494(17) -0.0073(13) -0.0093(13) 0.0132(14) O2 0.050(2) 0.0490(18) 0.0402(17) -0.0113(14) 0.0145(15) 0.0030(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 C1 N1 1.334(5) . ? C1 C2 1.398(6) . ? C1 H1 0.9300 . ? C2 C3 1.386(6) . ? C2 H2 0.9300 . ? C3 C4 1.362(6) . ? C3 H3 0.9300 . ? C4 C5 1.397(6) . ? C4 H4 0.9300 . ? C5 N1 1.358(5) . ? C5 C6 1.474(6) . ? C6 N2 1.471(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.318(6) . ? C7 N2 1.392(5) . ? C7 H7 0.9300 . ? C8 N3 1.400(5) . ? C8 H8 0.9300 . ? C9 N2 1.341(5) . ? C9 N3 1.368(5) . ? C9 Ru1 2.027(4) . ? C10 N3 1.456(5) . ? C10 C11 1.548(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.547(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.546(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O1 1.129(5) . ? C14 Ru1 1.868(4) . ? C15 O2 1.109(5) . ? C15 Ru1 1.876(4) . ? Cl1 Ru1 2.4344(10) . ? Cl2 Ru1 2.4861(11) . ? Ru1 N1 2.172(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.5(4) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 116.6(4) . . ? C3 C2 H2 121.7 . . ? C1 C2 H2 121.7 . . ? C4 C3 C2 121.3(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 119.3(4) . . ? N1 C5 C6 119.7(4) . . ? C4 C5 C6 121.0(4) . . ? N2 C6 C5 110.3(3) . . ? N2 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N2 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C8 C7 N2 107.0(4) . . ? C8 C7 H7 126.5 . . ? N2 C7 H7 126.5 . . ? C7 C8 N3 107.4(4) . . ? C7 C8 H8 126.3 . . ? N3 C8 H8 126.3 . . ? N2 C9 N3 104.6(3) . . ? N2 C9 Ru1 121.9(3) . . ? N3 C9 Ru1 133.4(3) . . ? N3 C10 C11 110.2(3) . . ? N3 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? N3 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 107.7(3) . . ? C12 C11 H11A 110.2 . . ? C10 C11 H11A 110.2 . . ? C12 C11 H11B 110.2 . . ? C10 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? C13 C12 C11 110.8(4) . . ? C13 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 Ru1 178.9(4) . . ? O2 C15 Ru1 176.7(4) . . ? C14 Ru1 C15 88.48(18) . . ? C14 Ru1 C9 95.51(16) . . ? C15 Ru1 C9 93.59(16) . . ? C14 Ru1 N1 177.41(15) . . ? C15 Ru1 N1 94.09(15) . . ? C9 Ru1 N1 84.59(15) . . ? C14 Ru1 Cl1 90.69(12) . . ? C15 Ru1 Cl1 176.39(13) . . ? C9 Ru1 Cl1 89.99(10) . . ? N1 Ru1 Cl1 86.73(9) . . ? C14 Ru1 Cl2 90.36(12) . . ? C15 Ru1 Cl2 85.68(12) . . ? C9 Ru1 Cl2 174.07(12) . . ? N1 Ru1 Cl2 89.59(9) . . ? Cl1 Ru1 Cl2 90.81(3) . . ? C1 N1 C5 120.5(4) . . ? C1 N1 Ru1 117.8(3) . . ? C5 N1 Ru1 121.6(3) . . ? C9 N2 C7 111.3(3) . . ? C9 N2 C6 124.0(4) . . ? C7 N2 C6 124.7(4) . . ? C9 N3 C8 109.7(3) . . ? C9 N3 C10 127.7(3) . . ? C8 N3 C10 122.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 2.0(6) . . . . ? C1 C2 C3 C4 -0.2(6) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? C3 C4 C5 N1 -0.7(6) . . . . ? C3 C4 C5 C6 -178.4(4) . . . . ? N1 C5 C6 N2 53.6(5) . . . . ? C4 C5 C6 N2 -128.6(4) . . . . ? N2 C7 C8 N3 -0.2(4) . . . . ? N3 C10 C11 C12 -174.2(4) . . . . ? C10 C11 C12 C13 158.2(4) . . . . ? N2 C9 Ru1 C14 -146.2(3) . . . . ? N3 C9 Ru1 C14 36.6(4) . . . . ? N2 C9 Ru1 C15 -57.4(3) . . . . ? N3 C9 Ru1 C15 125.4(4) . . . . ? N2 C9 Ru1 N1 36.4(3) . . . . ? N3 C9 Ru1 N1 -140.8(4) . . . . ? N2 C9 Ru1 Cl1 123.1(3) . . . . ? N3 C9 Ru1 Cl1 -54.1(4) . . . . ? C2 C1 N1 C5 -3.2(6) . . . . ? C2 C1 N1 Ru1 179.5(3) . . . . ? C4 C5 N1 C1 2.5(6) . . . . ? C6 C5 N1 C1 -179.7(3) . . . . ? C4 C5 N1 Ru1 179.6(3) . . . . ? C6 C5 N1 Ru1 -2.6(5) . . . . ? C15 Ru1 N1 C1 -125.8(3) . . . . ? C9 Ru1 N1 C1 141.0(3) . . . . ? Cl1 Ru1 N1 C1 50.7(3) . . . . ? Cl2 Ru1 N1 C1 -40.2(3) . . . . ? C15 Ru1 N1 C5 57.0(3) . . . . ? C9 Ru1 N1 C5 -36.2(3) . . . . ? Cl1 Ru1 N1 C5 -126.5(3) . . . . ? Cl2 Ru1 N1 C5 142.7(3) . . . . ? N3 C9 N2 C7 -1.1(4) . . . . ? Ru1 C9 N2 C7 -179.0(3) . . . . ? N3 C9 N2 C6 179.1(3) . . . . ? Ru1 C9 N2 C6 1.2(5) . . . . ? C8 C7 N2 C9 0.9(5) . . . . ? C8 C7 N2 C6 -179.4(4) . . . . ? C5 C6 N2 C9 -55.9(5) . . . . ? C5 C6 N2 C7 124.4(4) . . . . ? N2 C9 N3 C8 1.0(4) . . . . ? Ru1 C9 N3 C8 178.5(3) . . . . ? N2 C9 N3 C10 -177.0(3) . . . . ? Ru1 C9 N3 C10 0.5(6) . . . . ? C7 C8 N3 C9 -0.5(5) . . . . ? C7 C8 N3 C10 177.7(4) . . . . ? C11 C10 N3 C9 111.2(4) . . . . ? C11 C10 N3 C8 -66.5(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 0.396 _refine_diff_density_min -0.836 _refine_diff_density_rms 0.095