data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Bergman, Robert' _publ_contact_author_email rbergman@berkeley.edu loop_ _publ_author_name M.Crimmin D.Colby J.Ellman R.Bergman data_compound1f _database_code_depnum_ccdc_archive 'CCDC 794635' #TrackingRef '- compound1f_2a_3c_4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 N3' _chemical_formula_weight 239.32 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8213(14) _cell_length_b 9.2284(15) _cell_length_c 9.3398(15) _cell_angle_alpha 80.219(2) _cell_angle_beta 75.043(2) _cell_angle_gamma 62.591(2) _cell_volume 650.94(18) _cell_formula_units_Z 2 _cell_measurement_temperature 155(2) _cell_measurement_reflns_used 2845 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 25.33 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9730 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details 'Blessing, 1993' _exptl_special_details ; ? ; _diffrn_ambient_temperature 155(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0.833 _diffrn_reflns_number 4997 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2340 _reflns_number_gt 1838 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.1553P] 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 2340 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 N1 N 0.37590(16) 0.37688(15) 0.53231(13) 0.0304(3) Uani 1 1 d . . . N2 N 0.59770(15) 0.20795(14) 0.66154(12) 0.0300(3) Uani 1 1 d . . . C6 C 0.27933(17) 0.39559(16) 0.42517(14) 0.0263(3) Uani 1 1 d . . . N3 N 0.45887(15) 0.26635(14) 0.79100(12) 0.0313(3) Uani 1 1 d . . . C13 C 0.54292(17) 0.26304(16) 0.53861(15) 0.0258(3) Uani 1 1 d . . . C5 C 0.16447(18) 0.55110(17) 0.38316(15) 0.0314(3) Uani 1 1 d . . . H5A H 0.1546 0.6438 0.4231 0.038 Uiso 1 1 calc R . . C8 C 0.65878(19) 0.31872(18) 0.27152(15) 0.0307(3) Uani 1 1 d . . . H8A H 0.5573 0.4198 0.2716 0.037 Uiso 1 1 calc R . . C12 C 0.82459(18) 0.06558(17) 0.39605(16) 0.0328(3) Uani 1 1 d . . . H12A H 0.8369 -0.0077 0.4817 0.039 Uiso 1 1 calc R . . C1 C 0.29352(19) 0.26044(18) 0.36567(15) 0.0320(3) Uani 1 1 d . . . H1B H 0.3726 0.1534 0.3936 0.038 Uiso 1 1 calc R . . C7 C 0.67514(17) 0.21321(16) 0.39858(14) 0.0270(3) Uani 1 1 d . . . C2 C 0.1922(2) 0.2824(2) 0.26586(16) 0.0387(4) Uani 1 1 d . . . H2B H 0.2018 0.1900 0.2255 0.046 Uiso 1 1 calc R . . C4 C 0.06406(19) 0.5713(2) 0.28284(16) 0.0377(4) Uani 1 1 d . . . H4A H -0.0145 0.6782 0.2540 0.045 Uiso 1 1 calc R . . C11 C 0.9553(2) 0.02469(19) 0.26963(17) 0.0384(4) Uani 1 1 d . . . H11A H 1.0575 -0.0759 0.2691 0.046 Uiso 1 1 calc R . . C9 C 0.7896(2) 0.27687(19) 0.14533(16) 0.0358(4) Uani 1 1 d . . . H9A H 0.7778 0.3494 0.0591 0.043 Uiso 1 1 calc R . . C3 C 0.0772(2) 0.4372(2) 0.22422(16) 0.0409(4) Uani 1 1 d . . . H3A H 0.0076 0.4515 0.1558 0.049 Uiso 1 1 calc R . . C10 C 0.9375(2) 0.1301(2) 0.14411(17) 0.0382(4) Uani 1 1 d . . . H10A H 1.0269 0.1015 0.0571 0.046 Uiso 1 1 calc R . . C15 C 0.3789(2) 0.1527(2) 0.83248(17) 0.0410(4) Uani 1 1 d . . . H15A H 0.3245 0.1547 0.7526 0.061 Uiso 1 1 calc R . . H15B H 0.2900 0.1857 0.9240 0.061 Uiso 1 1 calc R . . H15C H 0.4688 0.0419 0.8486 0.061 Uiso 1 1 calc R . . C14 C 0.5407(2) 0.2646(2) 0.90907(16) 0.0403(4) Uani 1 1 d . . . H14A H 0.5936 0.3410 0.8804 0.060 Uiso 1 1 calc R . . H14B H 0.6310 0.1541 0.9253 0.060 Uiso 1 1 calc R . . H14C H 0.4523 0.2977 1.0008 0.060 Uiso 1 1 calc R . . H1A H 0.315(2) 0.421(2) 0.6148(19) 0.044(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0295(7) 0.0333(7) 0.0271(7) -0.0056(5) -0.0084(5) -0.0099(6) N2 0.0293(7) 0.0323(7) 0.0281(6) 0.0020(5) -0.0060(5) -0.0143(6) C6 0.0247(7) 0.0330(8) 0.0236(7) -0.0004(6) -0.0045(6) -0.0154(6) N3 0.0319(7) 0.0362(7) 0.0253(6) 0.0018(5) -0.0052(5) -0.0161(6) C13 0.0271(7) 0.0240(7) 0.0302(7) 0.0019(5) -0.0088(6) -0.0141(6) C5 0.0306(8) 0.0317(8) 0.0351(8) 0.0016(6) -0.0085(6) -0.0167(7) C8 0.0320(8) 0.0344(8) 0.0315(8) -0.0007(6) -0.0100(6) -0.0178(7) C12 0.0331(8) 0.0302(8) 0.0377(8) 0.0003(6) -0.0074(7) -0.0167(7) C1 0.0311(8) 0.0330(8) 0.0336(8) -0.0027(6) -0.0042(6) -0.0164(7) C7 0.0300(8) 0.0306(8) 0.0286(7) -0.0013(6) -0.0084(6) -0.0191(7) C2 0.0385(9) 0.0507(10) 0.0373(9) -0.0106(7) -0.0051(7) -0.0269(8) C4 0.0315(8) 0.0437(9) 0.0397(9) 0.0100(7) -0.0135(7) -0.0191(8) C11 0.0329(9) 0.0335(8) 0.0488(9) -0.0108(7) -0.0017(7) -0.0152(7) C9 0.0425(9) 0.0493(10) 0.0289(8) -0.0001(7) -0.0096(7) -0.0308(8) C3 0.0361(9) 0.0648(11) 0.0330(8) 0.0002(8) -0.0119(7) -0.0301(9) C10 0.0385(9) 0.0506(10) 0.0351(8) -0.0140(7) 0.0020(7) -0.0287(8) C15 0.0376(9) 0.0487(10) 0.0385(9) 0.0015(7) -0.0038(7) -0.0239(8) C14 0.0444(9) 0.0500(10) 0.0295(8) 0.0019(7) -0.0100(7) -0.0234(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C13 1.3699(17) . ? N1 C6 1.4152(17) . ? N1 H1A 0.861(17) . ? N2 C13 1.2931(16) . ? N2 N3 1.4496(16) . ? C6 C5 1.3839(19) . ? C6 C1 1.3914(19) . ? N3 C14 1.4599(18) . ? N3 C15 1.4660(18) . ? C13 C7 1.4850(19) . ? C5 C4 1.3835(19) . ? C5 H5A 0.9500 . ? C8 C9 1.383(2) . ? C8 C7 1.3941(19) . ? C8 H8A 0.9500 . ? C12 C11 1.384(2) . ? C12 C7 1.3914(19) . ? C12 H12A 0.9500 . ? C1 C2 1.381(2) . ? C1 H1B 0.9500 . ? C2 C3 1.378(2) . ? C2 H2B 0.9500 . ? C4 C3 1.382(2) . ? C4 H4A 0.9500 . ? C11 C10 1.383(2) . ? C11 H11A 0.9500 . ? C9 C10 1.381(2) . ? C9 H9A 0.9500 . ? C3 H3A 0.9500 . ? C10 H10A 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C13 N1 C6 127.47(12) . . ? C13 N1 H1A 114.5(11) . . ? C6 N1 H1A 115.3(11) . . ? C13 N2 N3 112.51(11) . . ? C5 C6 C1 119.70(12) . . ? C5 C6 N1 119.10(12) . . ? C1 C6 N1 121.16(13) . . ? N2 N3 C14 106.57(11) . . ? N2 N3 C15 108.11(11) . . ? C14 N3 C15 110.07(11) . . ? N2 C13 N1 123.16(13) . . ? N2 C13 C7 117.06(12) . . ? N1 C13 C7 119.37(12) . . ? C4 C5 C6 119.90(13) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C9 C8 C7 120.29(14) . . ? C9 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? C11 C12 C7 120.46(14) . . ? C11 C12 H12A 119.8 . . ? C7 C12 H12A 119.8 . . ? C2 C1 C6 119.77(14) . . ? C2 C1 H1B 120.1 . . ? C6 C1 H1B 120.1 . . ? C12 C7 C8 118.97(13) . . ? C12 C7 C13 120.12(12) . . ? C8 C7 C13 120.71(13) . . ? C3 C2 C1 120.64(14) . . ? C3 C2 H2B 119.7 . . ? C1 C2 H2B 119.7 . . ? C3 C4 C5 120.50(14) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C10 C11 C12 120.07(15) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C10 C9 C8 120.25(14) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C2 C3 C4 119.49(13) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C9 C10 C11 119.96(14) . . ? C9 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C13 N1 C6 C5 -145.19(14) . . . . ? C13 N1 C6 C1 37.1(2) . . . . ? C13 N2 N3 C14 -153.62(12) . . . . ? C13 N2 N3 C15 88.09(13) . . . . ? N3 N2 C13 N1 6.25(17) . . . . ? N3 N2 C13 C7 178.93(11) . . . . ? C6 N1 C13 N2 -150.55(13) . . . . ? C6 N1 C13 C7 36.93(19) . . . . ? C1 C6 C5 C4 0.2(2) . . . . ? N1 C6 C5 C4 -177.52(12) . . . . ? C5 C6 C1 C2 -0.4(2) . . . . ? N1 C6 C1 C2 177.34(13) . . . . ? C11 C12 C7 C8 0.40(19) . . . . ? C11 C12 C7 C13 -174.43(12) . . . . ? C9 C8 C7 C12 -0.16(19) . . . . ? C9 C8 C7 C13 174.64(12) . . . . ? N2 C13 C7 C12 27.82(17) . . . . ? N1 C13 C7 C12 -159.21(12) . . . . ? N2 C13 C7 C8 -146.92(13) . . . . ? N1 C13 C7 C8 26.06(18) . . . . ? C6 C1 C2 C3 0.2(2) . . . . ? C6 C5 C4 C3 0.1(2) . . . . ? C7 C12 C11 C10 -0.6(2) . . . . ? C7 C8 C9 C10 0.1(2) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C5 C4 C3 C2 -0.3(2) . . . . ? C8 C9 C10 C11 -0.3(2) . . . . ? C12 C11 C10 C9 0.5(2) . . . . ? N2 C13 N1 H1A 9.8(12) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.160 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.031 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 794636' #TrackingRef '- compound1f_2a_3c_4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H29 Cl4 N3 Ru' _chemical_formula_weight 566.34 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' 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.3261(7) _cell_length_b 13.8183(9) _cell_length_c 17.4025(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2483.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7277 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 25.16 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7825 _exptl_absorpt_correction_T_max 0.9685 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0.833 _diffrn_reflns_number 18334 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.38 _reflns_number_total 4566 _reflns_number_gt 3934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+5.1811P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(6) _refine_ls_number_reflns 4566 _refine_ls_number_parameters 274 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.084 _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 1.37534(6) 0.45693(3) -0.20333(3) 0.03338(15) Uani 1 1 d . . . Cl1 Cl 1.3882(3) 0.33439(13) -0.30185(11) 0.0611(6) Uani 1 1 d . . . Cl2 Cl 1.61546(18) 0.14562(11) -0.02610(9) 0.0358(4) Uani 1 1 d . . . Cl3 Cl 1.3831(3) 0.91724(19) 0.08369(14) 0.0731(10) Uani 0.876(6) 1 d P . . Cl4 Cl 1.2460(3) 1.0085(2) -0.04190(17) 0.0711(10) Uani 0.901(6) 1 d P . . Cl5 Cl 1.4674(7) 0.9171(4) -0.0654(4) 0.027(2) Uani 0.224(6) 1 d P . . N1 N 1.4276(5) 0.3417(4) -0.1237(3) 0.0307(13) Uani 1 1 d . . . N2 N 1.5523(5) 0.3060(4) -0.1488(3) 0.0315(13) Uani 1 1 d . . . H2A H 1.5774 0.2461 -0.1401 0.038 Uiso 1 1 calc R . . N3 N 1.5765(5) 0.4499(4) -0.2097(3) 0.0384(13) Uani 1 1 d . . . C1 C 1.2594(9) 0.6907(6) -0.0212(5) 0.056(2) Uani 1 1 d . . . H1A H 1.1726 0.6620 -0.0222 0.085 Uiso 1 1 calc R . . H1B H 1.2614 0.7479 -0.0544 0.085 Uiso 1 1 calc R . . H1C H 1.2809 0.7096 0.0316 0.085 Uiso 1 1 calc R . . C2 C 1.4962(7) 0.6520(6) -0.0505(5) 0.0468(19) Uani 1 1 d . . . H2B H 1.5544 0.6011 -0.0690 0.070 Uiso 1 1 calc R . . H2C H 1.5210 0.6706 0.0018 0.070 Uiso 1 1 calc R . . H2D H 1.5024 0.7085 -0.0843 0.070 Uiso 1 1 calc R . . C3 C 1.3599(9) 0.6153(4) -0.0503(4) 0.0425(18) Uani 1 1 d . . . H3A H 1.3569 0.5591 -0.0141 0.051 Uiso 1 1 calc R . . C4 C 1.3176(7) 0.5790(5) -0.1268(4) 0.0342(16) Uani 1 1 d D . . C5 C 1.2138(6) 0.5087(4) -0.1343(4) 0.0340(16) Uani 1 1 d D . . H5A H 1.1896 0.4704 -0.0877 0.041 Uiso 1 1 calc R . . C6 C 1.1616(7) 0.4805(5) -0.2041(4) 0.0435(17) Uani 1 1 d D . . H6A H 1.1021 0.4235 -0.2062 0.052 Uiso 1 1 calc R . . C7 C 1.2118(7) 0.5186(5) -0.2724(4) 0.0420(19) Uani 1 1 d D . . C8 C 1.1581(8) 0.4875(5) -0.3517(4) 0.052(2) Uani 1 1 d . . . H8A H 1.0861 0.5300 -0.3661 0.078 Uiso 1 1 calc R . . H8B H 1.1274 0.4205 -0.3489 0.078 Uiso 1 1 calc R . . H8C H 1.2268 0.4924 -0.3904 0.078 Uiso 1 1 calc R . . C9 C 1.3184(7) 0.5851(4) -0.2689(4) 0.0320(16) Uani 1 1 d D . . H9A H 1.3662 0.6010 -0.3172 0.038 Uiso 1 1 calc R . . C10 C 1.3690(8) 0.6151(4) -0.1991(4) 0.0352(14) Uani 1 1 d D . . H10A H 1.4523 0.6520 -0.1987 0.042 Uiso 1 1 calc R . . C11 C 1.3361(6) 0.2590(4) -0.1254(4) 0.0343(16) Uani 1 1 d . . . H11A H 1.3644 0.2097 -0.0885 0.051 Uiso 1 1 calc R . . H11B H 1.3344 0.2311 -0.1771 0.051 Uiso 1 1 calc R . . H11C H 1.2492 0.2816 -0.1116 0.051 Uiso 1 1 calc R . . C12 C 1.4458(7) 0.3731(5) -0.0428(3) 0.0332(15) Uani 1 1 d . . . H12A H 1.4689 0.3171 -0.0111 0.050 Uiso 1 1 calc R . . H12B H 1.3652 0.4018 -0.0237 0.050 Uiso 1 1 calc R . . H12C H 1.5154 0.4213 -0.0403 0.050 Uiso 1 1 calc R . . C13 C 1.6552(8) 0.5240(4) -0.2490(4) 0.050(2) Uani 1 1 d . . . H13A H 1.7470 0.5069 -0.2451 0.074 Uiso 1 1 calc R . . H13B H 1.6407 0.5871 -0.2247 0.074 Uiso 1 1 calc R . . H13C H 1.6301 0.5274 -0.3032 0.074 Uiso 1 1 calc R . . C14 C 1.6272(7) 0.3696(4) -0.1860(3) 0.0302(13) Uani 1 1 d . . . C15 C 1.7619(6) 0.3325(4) -0.2021(4) 0.0331(14) Uani 1 1 d . . . C16 C 1.8424(7) 0.3032(5) -0.1423(4) 0.0373(17) Uani 1 1 d . . . H16A H 1.8165 0.3113 -0.0903 0.045 Uiso 1 1 calc R . . C17 C 1.9621(7) 0.2617(6) -0.1603(4) 0.0418(18) Uani 1 1 d . . . H17A H 2.0191 0.2434 -0.1200 0.050 Uiso 1 1 calc R . . C18 C 1.9986(7) 0.2472(6) -0.2348(5) 0.0435(18) Uani 1 1 d . . . H18A H 2.0789 0.2167 -0.2459 0.052 Uiso 1 1 calc R . . C19 C 1.9195(7) 0.2764(5) -0.2933(5) 0.0443(18) Uani 1 1 d . . . H19A H 1.9461 0.2672 -0.3451 0.053 Uiso 1 1 calc R . . C20 C 1.8022(7) 0.3188(5) -0.2783(4) 0.0396(18) Uani 1 1 d . . . H20A H 1.7481 0.3389 -0.3195 0.048 Uiso 1 1 calc R . . C21 C 1.3998(8) 0.9633(8) -0.0114(6) 0.083(3) 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 0.0516(3) 0.0218(2) 0.0268(2) 0.0032(2) 0.0098(3) 0.0082(3) Cl1 0.0996(16) 0.0509(10) 0.0327(9) -0.0137(8) -0.0125(13) 0.0404(12) Cl2 0.0361(9) 0.0366(8) 0.0348(8) 0.0090(6) -0.0023(8) 0.0012(8) Cl3 0.087(2) 0.0726(17) 0.0596(16) 0.0054(12) -0.0211(17) -0.0166(17) Cl4 0.0546(14) 0.086(2) 0.0721(17) 0.0292(14) 0.0081(12) -0.0119(12) Cl5 0.032(4) 0.018(3) 0.031(4) -0.007(3) 0.008(3) 0.004(3) N1 0.035(3) 0.026(3) 0.031(3) 0.004(2) 0.003(2) 0.002(2) N2 0.036(3) 0.022(3) 0.036(3) -0.001(2) 0.008(3) 0.005(2) N3 0.052(3) 0.028(3) 0.035(3) 0.004(3) 0.017(3) 0.006(2) C1 0.075(6) 0.058(6) 0.037(5) -0.009(4) 0.003(4) 0.014(5) C2 0.047(5) 0.048(5) 0.045(5) 0.004(4) -0.003(4) -0.006(4) C3 0.075(6) 0.026(3) 0.027(3) -0.005(3) -0.006(4) 0.002(4) C4 0.052(4) 0.029(3) 0.022(3) -0.006(3) 0.004(3) 0.014(3) C5 0.038(4) 0.022(3) 0.043(4) 0.003(3) 0.003(3) 0.005(3) C6 0.048(4) 0.036(4) 0.047(4) 0.001(4) 0.010(4) 0.002(3) C7 0.053(5) 0.032(4) 0.041(4) -0.004(3) 0.003(3) 0.015(3) C8 0.062(6) 0.042(4) 0.053(5) -0.002(3) -0.016(4) 0.002(4) C9 0.049(4) 0.020(3) 0.027(3) 0.002(3) -0.001(3) 0.003(3) C10 0.053(4) 0.020(3) 0.032(3) -0.004(3) -0.001(4) 0.007(3) C11 0.037(4) 0.019(3) 0.047(4) 0.001(3) 0.002(3) 0.001(3) C12 0.045(4) 0.032(4) 0.023(3) -0.001(3) 0.003(3) -0.005(3) C13 0.072(6) 0.026(4) 0.051(4) 0.013(3) 0.032(4) -0.005(3) C14 0.044(4) 0.022(3) 0.024(3) 0.003(2) 0.004(3) -0.002(3) C15 0.040(4) 0.022(3) 0.037(4) 0.002(3) 0.005(4) -0.003(3) C16 0.039(5) 0.040(4) 0.032(4) -0.004(3) 0.008(3) -0.009(3) C17 0.033(4) 0.049(5) 0.044(5) 0.000(4) 0.001(3) -0.005(4) C18 0.028(4) 0.048(4) 0.054(5) -0.003(4) 0.008(4) -0.006(3) C19 0.045(4) 0.041(4) 0.047(4) -0.009(4) 0.018(4) -0.005(3) C20 0.047(4) 0.032(4) 0.040(5) -0.001(3) 0.001(3) -0.001(3) C21 0.048(5) 0.096(7) 0.106(8) 0.047(7) -0.005(5) -0.016(6) _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 N3 2.083(5) . ? Ru1 C5 2.176(7) . ? Ru1 N1 2.179(5) . ? Ru1 C9 2.187(6) . ? Ru1 C10 2.188(5) . ? Ru1 C4 2.230(6) . ? Ru1 C6 2.231(7) . ? Ru1 C7 2.242(7) . ? Ru1 Cl1 2.4132(18) . ? Cl3 C21 1.782(10) . ? Cl4 C21 1.787(10) . ? Cl5 C21 1.333(13) . ? N1 N2 1.446(7) . ? N1 C11 1.482(8) . ? N1 C12 1.486(8) . ? N2 C14 1.337(8) . ? N2 H2A 0.8800 . ? N3 C14 1.295(8) . ? N3 C13 1.475(8) . ? C1 C3 1.556(10) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.497(11) . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C2 H2D 0.9800 . ? C3 C4 1.488(9) . ? C3 H3A 1.0000 . ? C4 C5 1.452(9) . ? C4 C10 1.454(9) . ? C5 C6 1.385(10) . ? C5 H5A 1.0000 . ? C6 C7 1.400(10) . ? C6 H6A 1.0000 . ? C7 C9 1.434(10) . ? C7 C8 1.548(10) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.385(9) . ? C9 H9A 1.0000 . ? C10 H10A 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.508(9) . ? C15 C16 1.391(10) . ? C15 C20 1.404(10) . ? C16 C17 1.399(10) . ? C16 H16A 0.9500 . ? C17 C18 1.364(10) . ? C17 H17A 0.9500 . ? C18 C19 1.367(11) . ? C18 H18A 0.9500 . ? C19 C20 1.371(10) . ? C19 H19A 0.9500 . ? C20 H20A 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 N3 Ru1 C5 144.0(2) . . ? N3 Ru1 N1 75.7(2) . . ? C5 Ru1 N1 94.5(2) . . ? N3 Ru1 C9 106.2(2) . . ? C5 Ru1 C9 79.4(3) . . ? N1 Ru1 C9 172.0(2) . . ? N3 Ru1 C10 94.5(3) . . ? C5 Ru1 C10 68.3(3) . . ? N1 Ru1 C10 135.8(2) . . ? C9 Ru1 C10 36.9(2) . . ? N3 Ru1 C4 109.5(2) . . ? C5 Ru1 C4 38.5(2) . . ? N1 Ru1 C4 103.9(2) . . ? C9 Ru1 C4 68.1(2) . . ? C10 Ru1 C4 38.4(2) . . ? N3 Ru1 C6 173.3(2) . . ? C5 Ru1 C6 36.6(3) . . ? N1 Ru1 C6 110.8(2) . . ? C9 Ru1 C6 67.2(3) . . ? C10 Ru1 C6 79.9(3) . . ? C4 Ru1 C6 68.2(3) . . ? N3 Ru1 C7 137.8(2) . . ? C5 Ru1 C7 66.0(2) . . ? N1 Ru1 C7 143.7(2) . . ? C9 Ru1 C7 37.8(3) . . ? C10 Ru1 C7 67.4(3) . . ? C4 Ru1 C7 80.3(3) . . ? C6 Ru1 C7 36.5(3) . . ? N3 Ru1 Cl1 82.82(17) . . ? C5 Ru1 Cl1 131.65(19) . . ? N1 Ru1 Cl1 85.71(15) . . ? C9 Ru1 Cl1 102.26(17) . . ? C10 Ru1 Cl1 136.58(18) . . ? C4 Ru1 Cl1 165.80(19) . . ? C6 Ru1 Cl1 98.8(2) . . ? C7 Ru1 Cl1 85.82(18) . . ? N2 N1 C11 107.4(5) . . ? N2 N1 C12 105.8(5) . . ? C11 N1 C12 108.9(5) . . ? N2 N1 Ru1 106.1(3) . . ? C11 N1 Ru1 113.2(4) . . ? C12 N1 Ru1 114.8(4) . . ? C14 N2 N1 115.9(5) . . ? C14 N2 H2A 122.0 . . ? N1 N2 H2A 122.0 . . ? C14 N3 C13 121.4(6) . . ? C14 N3 Ru1 115.2(5) . . ? C13 N3 Ru1 122.8(4) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C3 C2 H2D 109.5 . . ? H2B C2 H2D 109.5 . . ? H2C C2 H2D 109.5 . . ? C4 C3 C2 112.9(6) . . ? C4 C3 C1 108.8(6) . . ? C2 C3 C1 113.6(6) . . ? C4 C3 H3A 107.1 . . ? C2 C3 H3A 107.1 . . ? C1 C3 H3A 107.1 . . ? C5 C4 C10 114.9(6) . . ? C5 C4 C3 121.5(6) . . ? C10 C4 C3 123.5(6) . . ? C5 C4 Ru1 68.7(3) . . ? C10 C4 Ru1 69.2(3) . . ? C3 C4 Ru1 135.3(5) . . ? C6 C5 C4 123.7(6) . . ? C6 C5 Ru1 73.9(4) . . ? C4 C5 Ru1 72.8(3) . . ? C6 C5 H5A 117.7 . . ? C4 C5 H5A 117.7 . . ? Ru1 C5 H5A 117.7 . . ? C5 C6 C7 119.7(6) . . ? C5 C6 Ru1 69.5(4) . . ? C7 C6 Ru1 72.2(4) . . ? C5 C6 H6A 119.5 . . ? C7 C6 H6A 119.5 . . ? Ru1 C6 H6A 119.5 . . ? C6 C7 C9 119.2(7) . . ? C6 C7 C8 121.3(7) . . ? C9 C7 C8 119.4(6) . . ? C6 C7 Ru1 71.4(4) . . ? C9 C7 Ru1 69.0(4) . . ? C8 C7 Ru1 130.0(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C7 121.3(6) . . ? C10 C9 Ru1 71.6(3) . . ? C7 C9 Ru1 73.2(4) . . ? C10 C9 H9A 119.0 . . ? C7 C9 H9A 119.0 . . ? Ru1 C9 H9A 119.0 . . ? C9 C10 C4 121.2(6) . . ? C9 C10 Ru1 71.5(3) . . ? C4 C10 Ru1 72.4(3) . . ? C9 C10 H10A 118.9 . . ? C4 C10 H10A 118.9 . . ? Ru1 C10 H10A 118.9 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 N2 118.9(6) . . ? N3 C14 C15 127.2(6) . . ? N2 C14 C15 113.6(5) . . ? C16 C15 C20 119.3(6) . . ? C16 C15 C14 120.8(6) . . ? C20 C15 C14 119.6(6) . . ? C15 C16 C17 118.7(7) . . ? C15 C16 H16A 120.6 . . ? C17 C16 H16A 120.6 . . ? C18 C17 C16 121.1(7) . . ? C18 C17 H17A 119.4 . . ? C16 C17 H17A 119.4 . . ? C17 C18 C19 120.0(7) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C18 C19 C20 120.8(8) . . ? C18 C19 H19A 119.6 . . ? C20 C19 H19A 119.6 . . ? C19 C20 C15 120.0(7) . . ? C19 C20 H20A 120.0 . . ? C15 C20 H20A 120.0 . . ? Cl5 C21 Cl3 122.3(8) . . ? Cl5 C21 Cl4 115.1(8) . . ? Cl3 C21 Cl4 108.3(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 N3 Ru1 N1 N2 -23.8(4) . . . . ? C5 Ru1 N1 N2 -168.7(4) . . . . ? C9 Ru1 N1 N2 -128.1(16) . . . . ? C10 Ru1 N1 N2 -105.4(5) . . . . ? C4 Ru1 N1 N2 -130.8(4) . . . . ? C6 Ru1 N1 N2 157.6(4) . . . . ? C7 Ru1 N1 N2 136.8(4) . . . . ? Cl1 Ru1 N1 N2 59.8(3) . . . . ? N3 Ru1 N1 C11 -141.4(5) . . . . ? C5 Ru1 N1 C11 73.8(4) . . . . ? C9 Ru1 N1 C11 114.3(17) . . . . ? C10 Ru1 N1 C11 137.0(5) . . . . ? C4 Ru1 N1 C11 111.7(4) . . . . ? C6 Ru1 N1 C11 40.0(5) . . . . ? C7 Ru1 N1 C11 19.3(6) . . . . ? Cl1 Ru1 N1 C11 -57.7(4) . . . . ? N3 Ru1 N1 C12 92.7(4) . . . . ? C5 Ru1 N1 C12 -52.1(5) . . . . ? C9 Ru1 N1 C12 -11.6(19) . . . . ? C10 Ru1 N1 C12 11.1(6) . . . . ? C4 Ru1 N1 C12 -14.3(5) . . . . ? C6 Ru1 N1 C12 -85.9(5) . . . . ? C7 Ru1 N1 C12 -106.7(5) . . . . ? Cl1 Ru1 N1 C12 176.4(4) . . . . ? C11 N1 N2 C14 148.8(5) . . . . ? C12 N1 N2 C14 -94.9(6) . . . . ? Ru1 N1 N2 C14 27.5(6) . . . . ? C5 Ru1 N3 C14 97.7(5) . . . . ? N1 Ru1 N3 C14 20.0(4) . . . . ? C9 Ru1 N3 C14 -168.1(4) . . . . ? C10 Ru1 N3 C14 156.2(5) . . . . ? C4 Ru1 N3 C14 119.9(5) . . . . ? C6 Ru1 N3 C14 -172(2) . . . . ? C7 Ru1 N3 C14 -143.0(4) . . . . ? Cl1 Ru1 N3 C14 -67.4(4) . . . . ? C5 Ru1 N3 C13 -91.3(6) . . . . ? N1 Ru1 N3 C13 -169.1(5) . . . . ? C9 Ru1 N3 C13 2.8(6) . . . . ? C10 Ru1 N3 C13 -32.9(5) . . . . ? C4 Ru1 N3 C13 -69.2(5) . . . . ? C6 Ru1 N3 C13 -1(2) . . . . ? C7 Ru1 N3 C13 27.9(7) . . . . ? Cl1 Ru1 N3 C13 103.5(5) . . . . ? C2 C3 C4 C5 156.0(6) . . . . ? C1 C3 C4 C5 -76.9(7) . . . . ? C2 C3 C4 C10 -28.4(9) . . . . ? C1 C3 C4 C10 98.6(8) . . . . ? C2 C3 C4 Ru1 65.2(9) . . . . ? C1 C3 C4 Ru1 -167.8(6) . . . . ? N3 Ru1 C4 C5 -159.1(4) . . . . ? N1 Ru1 C4 C5 -79.7(4) . . . . ? C9 Ru1 C4 C5 100.7(4) . . . . ? C10 Ru1 C4 C5 129.1(6) . . . . ? C6 Ru1 C4 C5 27.5(4) . . . . ? C7 Ru1 C4 C5 63.4(4) . . . . ? Cl1 Ru1 C4 C5 51.7(9) . . . . ? N3 Ru1 C4 C10 71.8(4) . . . . ? C5 Ru1 C4 C10 -129.1(6) . . . . ? N1 Ru1 C4 C10 151.2(4) . . . . ? C9 Ru1 C4 C10 -28.4(4) . . . . ? C6 Ru1 C4 C10 -101.6(5) . . . . ? C7 Ru1 C4 C10 -65.7(4) . . . . ? Cl1 Ru1 C4 C10 -77.4(9) . . . . ? N3 Ru1 C4 C3 -45.3(8) . . . . ? C5 Ru1 C4 C3 113.8(8) . . . . ? N1 Ru1 C4 C3 34.2(8) . . . . ? C9 Ru1 C4 C3 -145.4(8) . . . . ? C10 Ru1 C4 C3 -117.1(9) . . . . ? C6 Ru1 C4 C3 141.4(8) . . . . ? C7 Ru1 C4 C3 177.3(8) . . . . ? Cl1 Ru1 C4 C3 165.6(5) . . . . ? C10 C4 C5 C6 -3.1(8) . . . . ? C3 C4 C5 C6 172.8(6) . . . . ? Ru1 C4 C5 C6 -56.2(5) . . . . ? C10 C4 C5 Ru1 53.1(5) . . . . ? C3 C4 C5 Ru1 -131.0(6) . . . . ? N3 Ru1 C5 C6 168.8(4) . . . . ? N1 Ru1 C5 C6 -119.4(4) . . . . ? C9 Ru1 C5 C6 65.9(4) . . . . ? C10 Ru1 C5 C6 102.7(4) . . . . ? C4 Ru1 C5 C6 133.9(6) . . . . ? C7 Ru1 C5 C6 28.7(4) . . . . ? Cl1 Ru1 C5 C6 -31.1(5) . . . . ? N3 Ru1 C5 C4 34.9(6) . . . . ? N1 Ru1 C5 C4 106.6(4) . . . . ? C9 Ru1 C5 C4 -68.1(4) . . . . ? C10 Ru1 C5 C4 -31.3(4) . . . . ? C6 Ru1 C5 C4 -133.9(6) . . . . ? C7 Ru1 C5 C4 -105.2(4) . . . . ? Cl1 Ru1 C5 C4 -165.1(3) . . . . ? C4 C5 C6 C7 1.8(8) . . . . ? Ru1 C5 C6 C7 -53.9(5) . . . . ? C4 C5 C6 Ru1 55.8(5) . . . . ? N3 Ru1 C6 C5 -100(2) . . . . ? N1 Ru1 C6 C5 68.3(4) . . . . ? C9 Ru1 C6 C5 -103.3(4) . . . . ? C10 Ru1 C6 C5 -67.0(4) . . . . ? C4 Ru1 C6 C5 -28.9(4) . . . . ? C7 Ru1 C6 C5 -132.4(6) . . . . ? Cl1 Ru1 C6 C5 157.0(4) . . . . ? N3 Ru1 C6 C7 33(2) . . . . ? C5 Ru1 C6 C7 132.4(6) . . . . ? N1 Ru1 C6 C7 -159.3(4) . . . . ? C9 Ru1 C6 C7 29.1(4) . . . . ? C10 Ru1 C6 C7 65.4(4) . . . . ? C4 Ru1 C6 C7 103.6(4) . . . . ? Cl1 Ru1 C6 C7 -70.6(4) . . . . ? C5 C6 C7 C9 1.1(9) . . . . ? Ru1 C6 C7 C9 -51.6(5) . . . . ? C5 C6 C7 C8 178.8(6) . . . . ? Ru1 C6 C7 C8 126.0(6) . . . . ? C5 C6 C7 Ru1 52.7(5) . . . . ? N3 Ru1 C7 C6 -174.6(4) . . . . ? C5 Ru1 C7 C6 -28.8(4) . . . . ? N1 Ru1 C7 C6 33.9(6) . . . . ? C9 Ru1 C7 C6 -132.9(6) . . . . ? C10 Ru1 C7 C6 -104.1(4) . . . . ? C4 Ru1 C7 C6 -66.3(4) . . . . ? Cl1 Ru1 C7 C6 110.8(4) . . . . ? N3 Ru1 C7 C9 -41.7(5) . . . . ? C5 Ru1 C7 C9 104.2(4) . . . . ? N1 Ru1 C7 C9 166.8(4) . . . . ? C10 Ru1 C7 C9 28.8(4) . . . . ? C4 Ru1 C7 C9 66.6(4) . . . . ? C6 Ru1 C7 C9 132.9(6) . . . . ? Cl1 Ru1 C7 C9 -116.2(4) . . . . ? N3 Ru1 C7 C8 69.7(8) . . . . ? C5 Ru1 C7 C8 -144.4(8) . . . . ? N1 Ru1 C7 C8 -81.8(8) . . . . ? C9 Ru1 C7 C8 111.4(8) . . . . ? C10 Ru1 C7 C8 140.2(7) . . . . ? C4 Ru1 C7 C8 178.0(7) . . . . ? C6 Ru1 C7 C8 -115.7(8) . . . . ? Cl1 Ru1 C7 C8 -4.8(7) . . . . ? C6 C7 C9 C10 -2.6(10) . . . . ? C8 C7 C9 C10 179.7(6) . . . . ? Ru1 C7 C9 C10 -55.3(6) . . . . ? C6 C7 C9 Ru1 52.7(6) . . . . ? C8 C7 C9 Ru1 -125.0(6) . . . . ? N3 Ru1 C9 C10 -75.5(5) . . . . ? C5 Ru1 C9 C10 67.9(5) . . . . ? N1 Ru1 C9 C10 26.6(19) . . . . ? C4 Ru1 C9 C10 29.4(4) . . . . ? C6 Ru1 C9 C10 104.1(5) . . . . ? C7 Ru1 C9 C10 132.2(6) . . . . ? Cl1 Ru1 C9 C10 -161.5(4) . . . . ? N3 Ru1 C9 C7 152.3(4) . . . . ? C5 Ru1 C9 C7 -64.3(4) . . . . ? N1 Ru1 C9 C7 -105.6(17) . . . . ? C10 Ru1 C9 C7 -132.2(6) . . . . ? C4 Ru1 C9 C7 -102.8(4) . . . . ? C6 Ru1 C9 C7 -28.2(4) . . . . ? Cl1 Ru1 C9 C7 66.3(4) . . . . ? C7 C9 C10 C4 1.2(9) . . . . ? Ru1 C9 C10 C4 -54.8(5) . . . . ? C7 C9 C10 Ru1 56.0(6) . . . . ? C5 C4 C10 C9 1.6(8) . . . . ? C3 C4 C10 C9 -174.3(7) . . . . ? Ru1 C4 C10 C9 54.4(5) . . . . ? C5 C4 C10 Ru1 -52.9(5) . . . . ? C3 C4 C10 Ru1 131.3(6) . . . . ? N3 Ru1 C10 C9 111.1(4) . . . . ? C5 Ru1 C10 C9 -101.5(5) . . . . ? N1 Ru1 C10 C9 -174.8(4) . . . . ? C4 Ru1 C10 C9 -132.8(6) . . . . ? C6 Ru1 C10 C9 -65.3(5) . . . . ? C7 Ru1 C10 C9 -29.4(4) . . . . ? Cl1 Ru1 C10 C9 26.8(6) . . . . ? N3 Ru1 C10 C4 -116.1(4) . . . . ? C5 Ru1 C10 C4 31.3(4) . . . . ? N1 Ru1 C10 C4 -42.1(6) . . . . ? C9 Ru1 C10 C4 132.8(6) . . . . ? C6 Ru1 C10 C4 67.5(4) . . . . ? C7 Ru1 C10 C4 103.4(5) . . . . ? Cl1 Ru1 C10 C4 159.6(3) . . . . ? C13 N3 C14 N2 178.1(6) . . . . ? Ru1 N3 C14 N2 -10.8(7) . . . . ? C13 N3 C14 C15 -8.4(10) . . . . ? Ru1 N3 C14 C15 162.7(5) . . . . ? N1 N2 C14 N3 -12.8(8) . . . . ? N1 N2 C14 C15 172.8(5) . . . . ? N3 C14 C15 C16 127.8(7) . . . . ? N2 C14 C15 C16 -58.4(8) . . . . ? N3 C14 C15 C20 -58.3(9) . . . . ? N2 C14 C15 C20 115.5(6) . . . . ? C20 C15 C16 C17 0.7(9) . . . . ? C14 C15 C16 C17 174.6(6) . . . . ? C15 C16 C17 C18 -2.0(11) . . . . ? C16 C17 C18 C19 2.3(12) . . . . ? C17 C18 C19 C20 -1.2(11) . . . . ? C18 C19 C20 C15 -0.1(10) . . . . ? C16 C15 C20 C19 0.3(9) . . . . ? C14 C15 C20 C19 -173.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.307 _refine_diff_density_min -1.113 _refine_diff_density_rms 0.099 data_compound3c _database_code_depnum_ccdc_archive 'CCDC 794637' #TrackingRef '- Compound_1f_2a_3c_4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common MRC_III_CpIrLCl _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 Cl Ir N3' _chemical_formula_weight 539.11 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.7105(11) _cell_length_b 12.4005(13) _cell_length_c 16.6567(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2005.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9887 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 25.35 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 6.798 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7274 _exptl_absorpt_correction_T_max 0.8221 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 27219 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3660 _reflns_number_gt 3396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.0188P)^2^+4.9066P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.005(12) _refine_ls_number_reflns 3660 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0624 _refine_ls_wR_factor_gt 0.0599 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_hydrogen_treatment constr 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 0.2202(9) 0.3759(5) 0.0917(4) 0.0230(15) Uani 1 1 d . . . C2 C 0.4315(7) 0.4033(6) 0.1649(5) 0.0278(19) Uani 1 1 d . . . H2A H 0.5044 0.3597 0.1894 0.042 Uiso 1 1 calc R . . H2B H 0.3878 0.4481 0.2062 0.042 Uiso 1 1 calc R . . H2C H 0.4714 0.4497 0.1234 0.042 Uiso 1 1 calc R . . C3 C 0.1376(9) 0.1466(6) 0.0269(5) 0.036(2) Uani 1 1 d . . . H3A H 0.2287 0.1622 0.0043 0.054 Uiso 1 1 calc R . . H3B H 0.0664 0.1654 -0.0124 0.054 Uiso 1 1 calc R . . H3C H 0.1312 0.0697 0.0398 0.054 Uiso 1 1 calc R . . C4 C -0.0207(7) 0.1855(8) 0.1336(5) 0.0335(18) Uani 1 1 d . . . H4A H -0.0364 0.2279 0.1823 0.050 Uiso 1 1 calc R . . H4B H -0.0259 0.1085 0.1465 0.050 Uiso 1 1 calc R . . H4C H -0.0912 0.2033 0.0936 0.050 Uiso 1 1 calc R . . C5 C 0.2159(8) 0.4929(5) 0.0709(4) 0.0211(15) Uani 1 1 d . . . C6 C 0.1357(7) 0.5612(6) 0.1175(4) 0.0252(16) Uani 1 1 d . . . H6 H 0.0889 0.5331 0.1630 0.030 Uiso 1 1 calc R . . C7 C 0.1227(8) 0.6705(6) 0.0988(5) 0.0330(19) Uani 1 1 d . . . H7 H 0.0692 0.7168 0.1318 0.040 Uiso 1 1 calc R . . C8 C 0.1880(8) 0.7100(6) 0.0320(5) 0.035(2) Uani 1 1 d . . . H8 H 0.1764 0.7836 0.0176 0.042 Uiso 1 1 calc R . . C9 C 0.2697(9) 0.6449(6) -0.0140(4) 0.0321(19) Uani 1 1 d . . . H9 H 0.3177 0.6742 -0.0587 0.038 Uiso 1 1 calc R . . C10 C 0.2826(9) 0.5356(6) 0.0044(4) 0.0274(16) Uani 1 1 d . . . H10 H 0.3373 0.4902 -0.0287 0.033 Uiso 1 1 calc R . . C11 C 0.2882(8) 0.0151(5) 0.2099(4) 0.0217(15) Uani 1 1 d . . . C12 C 0.3151(7) 0.0714(6) 0.2821(4) 0.0234(17) Uani 1 1 d . . . C13 C 0.4376(7) 0.1372(6) 0.2697(4) 0.0202(16) Uani 1 1 d . . . C14 C 0.4871(7) 0.1160(5) 0.1899(5) 0.0209(14) Uani 1 1 d . . . C15 C 0.3924(7) 0.0430(6) 0.1507(4) 0.0219(16) Uani 1 1 d . . . C16 C 0.4176(8) -0.0075(6) 0.0697(4) 0.0322(19) Uani 1 1 d . . . H16A H 0.3400 -0.0544 0.0558 0.048 Uiso 1 1 calc R . . H16B H 0.5024 -0.0503 0.0716 0.048 Uiso 1 1 calc R . . H16C H 0.4269 0.0492 0.0291 0.048 Uiso 1 1 calc R . . C17 C 0.6201(7) 0.1556(6) 0.1546(5) 0.030(2) Uani 1 1 d . . . H17A H 0.6648 0.2048 0.1925 0.045 Uiso 1 1 calc R . . H17B H 0.6014 0.1937 0.1042 0.045 Uiso 1 1 calc R . . H17C H 0.6808 0.0941 0.1441 0.045 Uiso 1 1 calc R . . C18 C 0.5055(7) 0.2064(6) 0.3316(4) 0.0298(19) Uani 1 1 d . . . H18A H 0.5860 0.2420 0.3080 0.045 Uiso 1 1 calc R . . H18B H 0.5349 0.1615 0.3769 0.045 Uiso 1 1 calc R . . H18C H 0.4402 0.2610 0.3506 0.045 Uiso 1 1 calc R . . C19 C 0.2382(8) 0.0620(6) 0.3593(4) 0.0302(19) Uani 1 1 d . . . H19A H 0.2797 0.1099 0.3994 0.045 Uiso 1 1 calc R . . H19B H 0.2425 -0.0126 0.3785 0.045 Uiso 1 1 calc R . . H19C H 0.1419 0.0825 0.3508 0.045 Uiso 1 1 calc R . . C20 C 0.1764(7) -0.0661(6) 0.1978(5) 0.0326(19) Uani 1 1 d . . . H20A H 0.1795 -0.0930 0.1425 0.049 Uiso 1 1 calc R . . H20B H 0.0868 -0.0323 0.2079 0.049 Uiso 1 1 calc R . . H20C H 0.1895 -0.1263 0.2351 0.049 Uiso 1 1 calc R . . N1 N 0.1173(6) 0.2108(5) 0.1007(4) 0.0264(15) Uani 1 1 d . . . N2 N 0.1096(6) 0.3229(5) 0.0718(4) 0.0249(14) Uani 1 1 d . . . N3 N 0.3292(6) 0.3328(5) 0.1291(3) 0.0237(15) Uani 1 1 d . . . Cl Cl 0.15597(18) 0.30901(18) 0.27441(10) 0.0295(4) Uani 1 1 d . . . Ir Ir 0.28331(3) 0.18918(2) 0.185742(15) 0.01852(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 0.028(4) 0.020(4) 0.020(4) -0.001(3) 0.002(4) 0.000(4) C2 0.022(4) 0.019(4) 0.042(5) 0.001(3) -0.006(3) -0.002(3) C3 0.049(5) 0.026(4) 0.033(5) -0.001(4) -0.019(4) -0.008(4) C4 0.020(4) 0.032(4) 0.048(5) 0.016(5) -0.008(3) -0.005(4) C5 0.024(3) 0.020(3) 0.019(4) -0.003(3) -0.008(4) -0.008(4) C6 0.028(4) 0.025(4) 0.023(4) 0.001(3) 0.009(3) -0.003(4) C7 0.032(4) 0.024(5) 0.043(5) -0.008(4) -0.005(4) 0.003(4) C8 0.045(5) 0.022(5) 0.038(5) 0.001(3) -0.011(4) -0.001(4) C9 0.045(5) 0.030(4) 0.020(4) 0.006(3) -0.006(4) -0.012(4) C10 0.028(4) 0.031(4) 0.023(4) 0.000(3) 0.001(4) 0.004(4) C11 0.021(3) 0.011(3) 0.033(4) -0.001(3) -0.001(3) 0.008(3) C12 0.026(4) 0.019(4) 0.026(4) 0.003(3) 0.000(3) 0.006(3) C13 0.017(4) 0.023(4) 0.021(4) 0.004(3) -0.002(3) 0.007(3) C14 0.022(3) 0.020(4) 0.021(4) 0.001(3) 0.000(3) 0.002(3) C15 0.021(4) 0.018(4) 0.027(4) 0.003(3) 0.007(3) 0.002(3) C16 0.040(5) 0.028(5) 0.029(5) -0.007(4) 0.003(4) 0.006(4) C17 0.025(4) 0.035(5) 0.030(4) -0.004(3) 0.004(3) 0.003(3) C18 0.032(4) 0.031(5) 0.027(4) 0.002(3) -0.007(3) 0.004(4) C19 0.040(5) 0.033(4) 0.018(4) 0.004(3) 0.009(3) 0.002(4) C20 0.036(4) 0.024(4) 0.039(5) 0.003(4) -0.002(4) -0.004(3) N1 0.026(3) 0.023(4) 0.031(3) 0.003(3) -0.005(3) -0.009(3) N2 0.028(3) 0.017(3) 0.029(3) -0.001(3) -0.004(3) -0.004(3) N3 0.024(3) 0.020(4) 0.027(3) 0.002(3) -0.002(3) -0.001(3) Cl 0.0334(9) 0.0315(10) 0.0235(9) -0.0026(9) 0.0041(7) 0.0098(11) Ir 0.01818(12) 0.01801(12) 0.01936(12) 0.00044(13) -0.00061(12) -0.00055(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 C1 N2 1.302(9) . ? C1 N3 1.339(9) . ? C1 C5 1.492(9) . ? C2 N3 1.452(9) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N1 1.478(9) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 N1 1.481(9) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C10 1.388(10) . ? C5 C6 1.388(10) . ? C6 C7 1.397(11) . ? C6 H6 0.9500 . ? C7 C8 1.370(11) . ? C7 H7 0.9500 . ? C8 C9 1.367(11) . ? C8 H8 0.9500 . ? C9 C10 1.396(10) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.415(9) . ? C11 C15 1.455(9) . ? C11 C20 1.495(10) . ? C11 Ir 2.196(6) . ? C12 C13 1.457(10) . ? C12 C19 1.492(9) . ? C12 Ir 2.192(7) . ? C13 C14 1.438(10) . ? C13 C18 1.495(10) . ? C13 Ir 2.149(7) . ? C14 C15 1.446(10) . ? C14 C17 1.501(9) . ? C14 Ir 2.178(6) . ? C15 C16 1.507(10) . ? C15 Ir 2.179(7) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N1 N2 1.474(8) . ? N1 Ir 2.162(6) . ? N3 Ir 2.065(6) . ? Cl Ir 2.4328(18) . ? 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 C1 N3 124.8(6) . . ? N2 C1 C5 114.1(7) . . ? N3 C1 C5 121.2(7) . . ? N3 C2 H2A 109.5 . . ? N3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C10 C5 C6 118.4(6) . . ? C10 C5 C1 122.9(7) . . ? C6 C5 C1 118.6(6) . . ? C5 C6 C7 121.2(7) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C6 119.1(7) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C9 C8 C7 120.8(7) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.1(7) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C5 C10 C9 120.3(7) . . ? C5 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C15 109.3(6) . . ? C12 C11 C20 125.5(7) . . ? C15 C11 C20 125.1(6) . . ? C12 C11 Ir 71.0(4) . . ? C15 C11 Ir 69.9(4) . . ? C20 C11 Ir 128.5(5) . . ? C11 C12 C13 107.9(6) . . ? C11 C12 C19 127.0(7) . . ? C13 C12 C19 125.1(6) . . ? C11 C12 Ir 71.3(4) . . ? C13 C12 Ir 68.8(4) . . ? C19 C12 Ir 127.8(5) . . ? C14 C13 C12 107.6(6) . . ? C14 C13 C18 126.5(6) . . ? C12 C13 C18 125.7(6) . . ? C14 C13 Ir 71.7(4) . . ? C12 C13 Ir 72.0(4) . . ? C18 C13 Ir 125.8(5) . . ? C13 C14 C15 108.6(6) . . ? C13 C14 C17 126.1(6) . . ? C15 C14 C17 125.1(7) . . ? C13 C14 Ir 69.5(4) . . ? C15 C14 Ir 70.6(4) . . ? C17 C14 Ir 129.3(5) . . ? C14 C15 C11 106.6(6) . . ? C14 C15 C16 124.1(6) . . ? C11 C15 C16 128.3(7) . . ? C14 C15 Ir 70.6(4) . . ? C11 C15 Ir 71.2(4) . . ? C16 C15 Ir 131.7(5) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C12 C19 H19A 109.5 . . ? C12 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C12 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C11 C20 H20A 109.5 . . ? C11 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C11 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 N1 C3 104.0(5) . . ? N2 N1 C4 105.9(6) . . ? C3 N1 C4 108.3(6) . . ? N2 N1 Ir 111.6(4) . . ? C3 N1 Ir 112.3(5) . . ? C4 N1 Ir 114.0(4) . . ? C1 N2 N1 110.5(6) . . ? C1 N3 C2 119.5(6) . . ? C1 N3 Ir 112.7(5) . . ? C2 N3 Ir 118.6(5) . . ? N3 Ir C13 113.9(3) . . ? N3 Ir N1 75.8(2) . . ? C13 Ir N1 169.5(2) . . ? N3 Ir C14 100.2(2) . . ? C13 Ir C14 38.8(3) . . ? N1 Ir C14 138.6(3) . . ? N3 Ir C15 119.3(2) . . ? C13 Ir C15 65.5(3) . . ? N1 Ir C15 106.9(3) . . ? C14 Ir C15 38.8(3) . . ? N3 Ir C12 151.6(2) . . ? C13 Ir C12 39.2(3) . . ? N1 Ir C12 131.8(2) . . ? C14 Ir C12 64.6(3) . . ? C15 Ir C12 64.8(3) . . ? N3 Ir C11 158.0(2) . . ? C13 Ir C11 64.6(3) . . ? N1 Ir C11 104.9(2) . . ? C14 Ir C11 64.2(3) . . ? C15 Ir C11 38.8(2) . . ? C12 Ir C11 37.6(3) . . ? N3 Ir Cl 81.98(17) . . ? C13 Ir Cl 98.20(19) . . ? N1 Ir Cl 86.73(17) . . ? C14 Ir Cl 134.2(2) . . ? C15 Ir Cl 156.62(19) . . ? C12 Ir Cl 91.96(19) . . ? C11 Ir Cl 120.00(19) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.812 _refine_diff_density_min -1.156 _refine_diff_density_rms 0.132 data_compound4a _database_code_depnum_ccdc_archive 'CCDC 794638' #TrackingRef '- Compound_1f_2a_3c_4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common MRC_II_055A1 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 Cl N3 Ru' _chemical_formula_weight 475.03 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.437(5) _cell_length_b 10.703(5) _cell_length_c 11.940(5) _cell_angle_alpha 110.278(5) _cell_angle_beta 90.291(5) _cell_angle_gamma 106.338(5) _cell_volume 1078.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9943 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 25.37 _exptl_crystal_description dimond _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 0.862 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9187 _exptl_absorpt_correction_T_max 0.9582 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23597 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.37 _reflns_number_total 3909 _reflns_number_gt 3793 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP _computing_publication_material WinGX _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^)+(0.0747P)^2^+0.8069P] 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 3909 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0265 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3414(3) 0.1913(3) 0.3019(2) 0.0202(5) Uani 1 1 d . . . C2 C 0.4865(3) 0.1966(3) 0.3357(2) 0.0226(5) Uani 1 1 d . . . H2 H 0.5623 0.2840 0.3623 0.027 Uiso 1 1 calc R . . C3 C 0.5218(3) 0.0780(3) 0.3312(3) 0.0276(6) Uani 1 1 d . . . H3 H 0.6211 0.0853 0.3545 0.033 Uiso 1 1 calc R . . C4 C 0.4141(3) -0.0513(3) 0.2932(3) 0.0291(6) Uani 1 1 d . . . H4 H 0.4396 -0.1329 0.2874 0.035 Uiso 1 1 calc R . . C5 C 0.2682(3) -0.0597(3) 0.2637(3) 0.0255(6) Uani 1 1 d . . . H5 H 0.1932 -0.1475 0.2382 0.031 Uiso 1 1 calc R . . C6 C 0.2314(3) 0.0602(3) 0.2715(2) 0.0202(5) Uani 1 1 d . . . C7 C 0.0814(3) 0.0633(3) 0.2436(2) 0.0205(5) Uani 1 1 d . . . C8 C -0.1053(3) 0.2962(4) 0.2854(3) 0.0327(7) Uani 1 1 d . . . H8A H -0.0921 0.2939 0.3660 0.049 Uiso 1 1 calc R . . H8B H -0.2086 0.2905 0.2663 0.049 Uiso 1 1 calc R . . H8C H -0.0388 0.3836 0.2827 0.049 Uiso 1 1 calc R . . C9 C -0.0872(3) 0.1757(3) 0.0760(3) 0.0286(6) Uani 1 1 d . . . H9A H -0.0626 0.0951 0.0201 0.043 Uiso 1 1 calc R . . H9B H -0.0205 0.2619 0.0713 0.043 Uiso 1 1 calc R . . H9C H -0.1903 0.1689 0.0547 0.043 Uiso 1 1 calc R . . C10 C -0.0737(3) -0.1302(3) 0.3044(2) 0.0235(5) Uani 1 1 d . . . H10 H 0.0215 -0.1136 0.3523 0.028 Uiso 1 1 calc R . . C11 C -0.1837(4) -0.0868(4) 0.3909(3) 0.0365(7) Uani 1 1 d . . . H11A H -0.1437 0.0128 0.4400 0.055 Uiso 1 1 calc R . . H11B H -0.2001 -0.1415 0.4432 0.055 Uiso 1 1 calc R . . H11C H -0.2781 -0.1037 0.3452 0.055 Uiso 1 1 calc R . . C12 C -0.1317(4) -0.2845(3) 0.2265(3) 0.0338(7) Uani 1 1 d . . . H12A H -0.0588 -0.3098 0.1717 0.051 Uiso 1 1 calc R . . H12B H -0.2258 -0.3028 0.1797 0.051 Uiso 1 1 calc R . . H12C H -0.1478 -0.3404 0.2778 0.051 Uiso 1 1 calc R . . C13 C 0.4977(3) 0.4722(3) 0.2702(2) 0.0212(5) Uani 1 1 d . . . H13 H 0.5937 0.4731 0.2957 0.025 Uiso 1 1 calc R . . C14 C 0.4262(3) 0.3785(3) 0.1546(2) 0.0214(5) Uani 1 1 d . . . C15 C 0.2864(3) 0.3853(3) 0.1176(2) 0.0219(5) Uani 1 1 d . . . H15 H 0.2336 0.3205 0.0426 0.026 Uiso 1 1 calc R . . C16 C 0.2238(3) 0.4891(3) 0.1922(3) 0.0240(5) Uani 1 1 d . . . H16 H 0.1358 0.4988 0.1620 0.029 Uiso 1 1 calc R . . C17 C 0.2901(3) 0.5758(3) 0.3082(3) 0.0249(6) Uani 1 1 d . . . C18 C 0.4282(3) 0.5639(3) 0.3477(2) 0.0233(6) Uani 1 1 d . . . H18 H 0.4734 0.6188 0.4275 0.028 Uiso 1 1 calc R . . C19 C 0.2151(3) 0.6696(3) 0.3940(3) 0.0316(6) Uani 1 1 d . . . H19A H 0.2793 0.7218 0.4703 0.047 Uiso 0.50 1 calc PR . . H19B H 0.1204 0.6131 0.4081 0.047 Uiso 0.50 1 calc PR . . H19C H 0.1967 0.7353 0.3596 0.047 Uiso 0.50 1 calc PR . . H19D H 0.1183 0.6584 0.3550 0.047 Uiso 0.50 1 calc PR . . H19E H 0.2772 0.7670 0.4173 0.047 Uiso 0.50 1 calc PR . . H19F H 0.2009 0.6448 0.4657 0.047 Uiso 0.50 1 calc PR . . C20 C 0.5023(3) 0.2779(3) 0.0744(2) 0.0237(5) Uani 1 1 d . . . H20 H 0.5640 0.2547 0.1282 0.028 Uiso 1 1 calc R . . C21 C 0.6079(4) 0.3511(3) 0.0045(3) 0.0366(8) Uani 1 1 d . . . H21A H 0.6570 0.2864 -0.0471 0.055 Uiso 1 1 calc R . . H21B H 0.6830 0.4329 0.0609 0.055 Uiso 1 1 calc R . . H21C H 0.5516 0.3809 -0.0453 0.055 Uiso 1 1 calc R . . C22 C 0.3944(4) 0.1411(3) -0.0089(3) 0.0362(7) Uani 1 1 d . . . H22A H 0.4502 0.0815 -0.0578 0.054 Uiso 1 1 calc R . . H22B H 0.3303 0.1604 -0.0616 0.054 Uiso 1 1 calc R . . H22C H 0.3331 0.0934 0.0389 0.054 Uiso 1 1 calc R . . N1 N -0.0700(2) 0.1778(2) 0.1976(2) 0.0247(5) Uani 1 1 d . . . N2 N 0.0788(2) 0.1783(2) 0.22796(19) 0.0197(4) Uani 1 1 d . . . N3 N -0.0435(3) -0.0448(3) 0.2280(2) 0.0268(5) Uani 1 1 d . . . Cl Cl 0.20388(7) 0.38633(7) 0.48721(6) 0.02498(17) Uani 1 1 d . . . Ru Ru 0.273714(18) 0.349751(18) 0.285832(15) 0.01704(11) Uani 1 1 d . . . H100 H -0.113(4) -0.021(4) 0.211(3) 0.038(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0199(12) 0.0213(13) 0.0201(12) 0.0086(10) 0.0045(10) 0.0062(10) C2 0.0198(12) 0.0254(14) 0.0239(13) 0.0111(11) 0.0025(10) 0.0061(10) C3 0.0210(13) 0.0320(16) 0.0333(15) 0.0131(12) 0.0037(11) 0.0116(12) C4 0.0288(14) 0.0249(14) 0.0387(16) 0.0140(12) 0.0059(12) 0.0126(12) C5 0.0245(14) 0.0202(13) 0.0310(14) 0.0099(11) 0.0025(11) 0.0045(11) C6 0.0202(12) 0.0224(13) 0.0185(12) 0.0092(10) 0.0029(9) 0.0049(10) C7 0.0200(12) 0.0205(13) 0.0188(12) 0.0074(10) 0.0017(9) 0.0023(10) C8 0.0200(13) 0.0445(18) 0.0371(16) 0.0156(14) 0.0067(11) 0.0138(12) C9 0.0255(14) 0.0305(16) 0.0289(14) 0.0108(12) -0.0040(11) 0.0074(12) C10 0.0217(13) 0.0220(13) 0.0268(13) 0.0132(11) -0.0009(10) 0.0012(10) C11 0.0407(18) 0.0417(19) 0.0373(17) 0.0220(15) 0.0088(14) 0.0182(15) C12 0.0380(16) 0.0229(15) 0.0363(16) 0.0120(12) -0.0020(13) 0.0013(12) C13 0.0174(12) 0.0218(13) 0.0233(13) 0.0104(10) 0.0047(10) 0.0013(10) C14 0.0187(12) 0.0204(13) 0.0254(13) 0.0118(11) 0.0054(10) 0.0020(10) C15 0.0214(12) 0.0221(13) 0.0245(13) 0.0144(11) 0.0030(10) 0.0026(10) C16 0.0228(13) 0.0256(14) 0.0301(14) 0.0183(11) 0.0063(11) 0.0067(11) C17 0.0287(14) 0.0180(13) 0.0317(14) 0.0143(11) 0.0081(11) 0.0062(11) C18 0.0262(14) 0.0186(13) 0.0203(13) 0.0059(10) 0.0046(10) 0.0008(11) C19 0.0378(16) 0.0268(15) 0.0351(16) 0.0134(12) 0.0100(13) 0.0145(13) C20 0.0205(12) 0.0219(13) 0.0276(13) 0.0091(11) 0.0049(10) 0.0046(10) C21 0.0393(17) 0.0276(16) 0.0383(17) 0.0106(13) 0.0198(14) 0.0047(13) C22 0.0327(16) 0.0250(15) 0.0406(17) 0.0039(13) 0.0098(13) 0.0031(12) N1 0.0145(10) 0.0281(12) 0.0341(12) 0.0159(10) -0.0007(9) 0.0047(9) N2 0.0160(10) 0.0234(11) 0.0199(10) 0.0099(9) -0.0012(8) 0.0035(8) N3 0.0194(11) 0.0261(13) 0.0351(13) 0.0177(10) -0.0041(10) -0.0008(10) Cl 0.0265(3) 0.0291(4) 0.0215(3) 0.0115(3) 0.0053(3) 0.0086(3) Ru 0.01504(15) 0.01697(16) 0.01953(16) 0.00843(10) 0.00224(9) 0.00319(10) _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 C2 1.405(4) . ? C1 C6 1.415(4) . ? C1 Ru 2.039(3) . ? C2 C3 1.384(4) . ? C2 H2 0.9500 . ? C3 C4 1.387(4) . ? C3 H3 0.9500 . ? C4 C5 1.389(4) . ? C4 H4 0.9500 . ? C5 C6 1.394(4) . ? C5 H5 0.9500 . ? C6 C7 1.465(4) . ? C7 N2 1.315(4) . ? C7 N3 1.357(4) . ? C8 N1 1.462(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 N1 1.451(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N3 1.478(4) . ? C10 C11 1.519(4) . ? C10 C12 1.521(4) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.411(4) . ? C13 C14 1.420(4) . ? C13 Ru 2.199(3) . ? C13 H13 0.9500 . ? C14 C15 1.418(4) . ? C14 C20 1.523(4) . ? C14 Ru 2.174(3) . ? C15 C16 1.437(4) . ? C15 Ru 2.168(3) . ? C15 H15 0.9500 . ? C16 C17 1.394(4) . ? C16 Ru 2.289(3) . ? C16 H16 0.9500 . ? C17 C18 1.437(4) . ? C17 C19 1.501(4) . ? C17 Ru 2.300(3) . ? C18 Ru 2.204(3) . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C19 H19D 0.9800 . ? C19 H19E 0.9800 . ? C19 H19F 0.9800 . ? C20 C22 1.520(4) . ? C20 C21 1.526(4) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 N2 1.446(3) . ? N2 Ru 2.106(2) . ? N3 H100 0.82(4) . ? Cl Ru 2.4244(11) . ? 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 C1 C6 116.4(2) . . ? C2 C1 Ru 127.1(2) . . ? C6 C1 Ru 116.49(19) . . ? C3 C2 C1 121.8(3) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 120.8(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 119.0(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 121.5(2) . . ? C5 C6 C7 124.8(2) . . ? C1 C6 C7 113.7(2) . . ? N2 C7 N3 122.4(2) . . ? N2 C7 C6 113.6(2) . . ? N3 C7 C6 123.9(2) . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 C11 110.1(2) . . ? N3 C10 C12 110.1(2) . . ? C11 C10 C12 111.1(2) . . ? N3 C10 H10 108.5 . . ? C11 C10 H10 108.5 . . ? C12 C10 H10 108.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 120.9(2) . . ? C18 C13 Ru 71.53(15) . . ? C14 C13 Ru 70.11(14) . . ? C18 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? Ru C13 H13 131.7 . . ? C15 C14 C13 117.8(2) . . ? C15 C14 C20 122.5(2) . . ? C13 C14 C20 119.6(2) . . ? C15 C14 Ru 70.70(15) . . ? C13 C14 Ru 72.00(15) . . ? C20 C14 Ru 129.51(19) . . ? C14 C15 C16 120.8(2) . . ? C14 C15 Ru 71.18(15) . . ? C16 C15 Ru 75.84(15) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? Ru C15 H15 125.0 . . ? C17 C16 C15 121.1(2) . . ? C17 C16 Ru 72.72(16) . . ? C15 C16 Ru 66.66(15) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? Ru C16 H16 134.8 . . ? C16 C17 C18 117.7(2) . . ? C16 C17 C19 121.9(3) . . ? C18 C17 C19 120.2(3) . . ? C16 C17 Ru 71.90(16) . . ? C18 C17 Ru 67.83(15) . . ? C19 C17 Ru 127.1(2) . . ? C13 C18 C17 121.2(2) . . ? C13 C18 Ru 71.10(15) . . ? C17 C18 Ru 75.04(16) . . ? C13 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? Ru C18 H18 126.4 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C19 H19D 109.5 . . ? H19A C19 H19D 141.1 . . ? H19B C19 H19D 56.3 . . ? H19C C19 H19D 56.3 . . ? C17 C19 H19E 109.5 . . ? H19A C19 H19E 56.3 . . ? H19B C19 H19E 141.1 . . ? H19C C19 H19E 56.3 . . ? H19D C19 H19E 109.5 . . ? C17 C19 H19F 109.5 . . ? H19A C19 H19F 56.3 . . ? H19B C19 H19F 56.3 . . ? H19C C19 H19F 141.1 . . ? H19D C19 H19F 109.5 . . ? H19E C19 H19F 109.5 . . ? C22 C20 C14 113.6(2) . . ? C22 C20 C21 111.5(3) . . ? C14 C20 C21 109.4(2) . . ? C22 C20 H20 107.4 . . ? C14 C20 H20 107.4 . . ? C21 C20 H20 107.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N2 N1 C9 110.4(2) . . ? N2 N1 C8 110.7(2) . . ? C9 N1 C8 112.0(2) . . ? C7 N2 N1 112.7(2) . . ? C7 N2 Ru 117.68(17) . . ? N1 N2 Ru 128.01(17) . . ? C7 N3 C10 124.6(2) . . ? C7 N3 H100 107(3) . . ? C10 N3 H100 115(3) . . ? C1 Ru N2 76.86(10) . . ? C1 Ru C15 119.33(10) . . ? N2 Ru C15 95.99(9) . . ? C1 Ru C14 92.71(10) . . ? N2 Ru C14 118.13(10) . . ? C15 Ru C14 38.12(10) . . ? C1 Ru C13 94.25(11) . . ? N2 Ru C13 154.88(10) . . ? C15 Ru C13 67.63(10) . . ? C14 Ru C13 37.89(10) . . ? C1 Ru C18 120.09(11) . . ? N2 Ru C18 162.48(10) . . ? C15 Ru C18 79.86(10) . . ? C14 Ru C18 68.43(10) . . ? C13 Ru C18 37.38(10) . . ? C1 Ru C16 156.81(10) . . ? N2 Ru C16 101.18(10) . . ? C15 Ru C16 37.50(10) . . ? C14 Ru C16 67.53(10) . . ? C13 Ru C16 77.74(10) . . ? C18 Ru C16 65.24(11) . . ? C1 Ru C17 157.11(11) . . ? N2 Ru C17 125.66(10) . . ? C15 Ru C17 66.92(10) . . ? C14 Ru C17 80.33(10) . . ? C13 Ru C17 66.91(10) . . ? C18 Ru C17 37.13(11) . . ? C16 Ru C17 35.38(10) . . ? C1 Ru Cl 85.68(7) . . ? N2 Ru Cl 86.21(6) . . ? C15 Ru Cl 154.78(8) . . ? C14 Ru Cl 154.62(7) . . ? C13 Ru Cl 116.89(7) . . ? C18 Ru Cl 90.50(7) . . ? C16 Ru Cl 117.40(7) . . ? C17 Ru Cl 91.38(7) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.636 _refine_diff_density_min -0.994 _refine_diff_density_rms 0.106