# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_so_a031 _iucr_refine_instructions_details ; TITL SO_A031 in P-1 CELL 0.71073 8.5108 9.7943 11.4935 100.446 90.126 100.326 ZERR 2.00 0.0004 0.0004 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H N S CL RU UNIT 32 28 8 2 6 2 MERG 2 FMAP 2 PLAN 5 SIZE 0.15 0.25 0.40 ACTA BOND $H CONF WGHT 0.01430 0.64850 L.S. 4 TEMP -173 FVAR 0.21575 RU1 6 0.233811 0.210099 0.245308 11.00000 0.00897 0.01025 = 0.00888 0.00108 0.00222 0.00128 CL1 5 0.448634 0.358515 0.176663 11.00000 0.01480 0.01395 = 0.01779 0.00339 0.00636 0.00064 CL2 5 0.047353 0.302666 0.146349 11.00000 0.01514 0.02136 = 0.01405 0.00509 0.00178 0.00653 CL3 5 0.404070 0.106390 0.345964 11.00000 0.01290 0.01570 = 0.01439 0.00388 0.00174 0.00377 S1 4 -0.173308 0.092555 0.478691 11.00000 0.01210 0.01375 = 0.01161 0.00098 0.00401 0.00030 N1 3 0.213748 0.349478 0.398809 11.00000 0.01106 0.01194 = 0.01130 0.00203 0.00073 0.00304 C16 1 0.294062 0.558295 0.545169 11.00000 0.01406 0.01221 = 0.02015 -0.00144 -0.00258 0.00183 AFIX 43 H1 2 0.362981 0.644110 0.569117 11.00000 -1.20000 AFIX 0 N3 3 0.039247 0.099489 0.318369 11.00000 0.01024 0.01224 = 0.01029 0.00181 0.00099 0.00179 N4 3 0.256319 0.070598 0.092892 11.00000 0.01122 0.01467 = 0.01363 0.00334 0.00231 0.00151 N5 3 0.269137 0.713744 0.282385 11.00000 0.03420 0.03112 = 0.02973 0.00020 0.01059 0.00454 C1 1 0.309792 0.474708 0.435852 11.00000 0.01186 0.01342 = 0.01735 0.00261 0.00123 0.00217 AFIX 43 H8 2 0.389452 0.506582 0.386777 11.00000 -1.20000 AFIX 0 C2 1 0.174519 0.512040 0.617772 11.00000 0.01809 0.01786 = 0.01276 -0.00228 -0.00082 0.00694 AFIX 43 H2 2 0.163032 0.565880 0.691638 11.00000 -1.20000 AFIX 0 C3 1 0.071770 0.384393 0.579304 11.00000 0.01489 0.01770 = 0.01267 0.00227 0.00262 0.00413 AFIX 43 H7 2 -0.010703 0.352372 0.626149 11.00000 -1.20000 AFIX 0 C4 1 0.094569 0.305735 0.469792 11.00000 0.01055 0.01316 = 0.01199 0.00276 0.00040 0.00341 C5 1 -0.002513 0.169904 0.419024 11.00000 0.01138 0.01351 = 0.01055 0.00382 0.00158 0.00313 C6 1 -0.194127 -0.047662 0.359569 11.00000 0.01399 0.01377 = 0.01055 0.00252 0.00045 0.00325 C7 1 -0.067583 -0.027277 0.282336 11.00000 0.01049 0.01228 = 0.01302 0.00334 -0.00057 0.00101 C8 1 -0.062596 -0.127197 0.179626 11.00000 0.01503 0.01604 = 0.01386 0.00104 0.00319 0.00151 AFIX 43 H6 2 0.020719 -0.115830 0.127991 11.00000 -1.20000 AFIX 0 C9 1 -0.184550 -0.243368 0.156648 11.00000 0.02034 0.01556 = 0.01602 -0.00149 0.00079 0.00036 AFIX 43 H5 2 -0.182707 -0.310690 0.088506 11.00000 -1.20000 AFIX 0 C10 1 -0.311276 -0.262340 0.233653 11.00000 0.01561 0.01522 = 0.01936 0.00258 -0.00176 -0.00261 AFIX 43 H4 2 -0.391723 -0.341611 0.215673 11.00000 -1.20000 AFIX 0 C11 1 -0.317840 -0.164580 0.335848 11.00000 0.01317 0.01752 = 0.01651 0.00538 0.00206 0.00050 AFIX 43 H3 2 -0.401713 -0.176314 0.386969 11.00000 -1.20000 AFIX 0 C12 1 0.286492 0.007763 0.005103 11.00000 0.01043 0.01581 = 0.01513 0.00425 0.00039 0.00186 C13 1 0.328755 -0.071177 -0.106573 11.00000 0.01699 0.02045 = 0.01413 -0.00194 0.00124 0.00563 AFIX 137 H9 2 0.379394 -0.006576 -0.154658 11.00000 -1.50000 H10 2 0.233865 -0.127648 -0.147306 11.00000 -1.50000 H11 2 0.400894 -0.131398 -0.091447 11.00000 -1.50000 AFIX 0 C14 1 0.266583 0.619971 0.057079 11.00000 0.05242 0.03088 = 0.02379 0.01037 0.00411 0.00790 AFIX 137 H12 2 0.366082 0.658454 0.026089 11.00000 -1.50000 H13 2 0.180146 0.647265 0.018473 11.00000 -1.50000 H14 2 0.253213 0.518844 0.043101 11.00000 -1.50000 AFIX 0 C15 1 0.267050 0.673287 0.183122 11.00000 0.01985 0.01897 = 0.02988 0.00633 0.00638 0.00383 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 END ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 Cl3 N3 Ru S, C2 H3 N' _chemical_formula_sum 'C16 H14 Cl3 N4 Ru S' _chemical_formula_weight 501.79 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' S S 0.1246 0.1234 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5108(4) _cell_length_b 9.7943(4) _cell_length_c 11.4935(5) _cell_angle_alpha 100.446(2) _cell_angle_beta 90.126(2) _cell_angle_gamma 100.326(2) _cell_volume 926.33(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3834 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 26.8 _exptl_crystal_description planar _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 1.398 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6047 _exptl_absorpt_correction_T_max 0.8176 _exptl_absorpt_process_details 'SADABS, Bruker 2012' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\w and \f-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13956 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.83 _reflns_number_total 3834 _reflns_number_gt 3736 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX2 (Bruker, 2012)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2012)' _computing_data_reduction 'SAINT-Plus (Bruker, 2012)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material 'PublCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0143P)^2^+0.6485P] 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 3834 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0165 _refine_ls_R_factor_gt 0.0159 _refine_ls_wR_factor_ref 0.0404 _refine_ls_wR_factor_gt 0.0400 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.233809(13) 0.210097(12) 0.245307(10) 0.00953(4) Uani 1 1 d . . . Cl1 Cl 0.44863(4) 0.35851(4) 0.17666(3) 0.01573(8) Uani 1 1 d . . . Cl2 Cl 0.04736(4) 0.30266(4) 0.14635(3) 0.01624(8) Uani 1 1 d . . . Cl3 Cl 0.40407(4) 0.10638(4) 0.34596(3) 0.01406(8) Uani 1 1 d . . . S1 S -0.17331(4) 0.09255(4) 0.47869(3) 0.01294(8) Uani 1 1 d . . . N1 N 0.21374(15) 0.34948(13) 0.39882(11) 0.0113(2) Uani 1 1 d . . . C16 C 0.29406(18) 0.55829(17) 0.54516(14) 0.0161(3) Uani 1 1 d . . . H1 H 0.3645 0.6460 0.5696 0.019 Uiso 1 1 calc R . . N3 N 0.03924(14) 0.09948(13) 0.31836(11) 0.0110(2) Uani 1 1 d . . . N4 N 0.25632(15) 0.07059(14) 0.09289(11) 0.0132(3) Uani 1 1 d . . . N5 N 0.2691(2) 0.71374(18) 0.28237(15) 0.0326(4) Uani 1 1 d . . . C1 C 0.30979(18) 0.47471(16) 0.43586(14) 0.0142(3) Uani 1 1 d . . . H8 H 0.3912 0.5073 0.3857 0.017 Uiso 1 1 calc R . . C2 C 0.17454(19) 0.51204(17) 0.61778(14) 0.0164(3) Uani 1 1 d . . . H2 H 0.1628 0.5670 0.6932 0.020 Uiso 1 1 calc R . . C3 C 0.07177(19) 0.38439(17) 0.57931(13) 0.0150(3) Uani 1 1 d . . . H7 H -0.0125 0.3517 0.6272 0.018 Uiso 1 1 calc R . . C4 C 0.09456(17) 0.30572(16) 0.46979(13) 0.0116(3) Uani 1 1 d . . . C5 C -0.00252(17) 0.16991(16) 0.41903(13) 0.0115(3) Uani 1 1 d . . . C6 C -0.19411(18) -0.04767(16) 0.35956(13) 0.0126(3) Uani 1 1 d . . . C7 C -0.06758(17) -0.02727(16) 0.28235(13) 0.0119(3) Uani 1 1 d . . . C8 C -0.06259(19) -0.12719(17) 0.17963(13) 0.0154(3) Uani 1 1 d . . . H6 H 0.0225 -0.1156 0.1269 0.018 Uiso 1 1 calc R . . C9 C -0.1845(2) -0.24337(17) 0.15665(14) 0.0182(3) Uani 1 1 d . . . H5 H -0.1826 -0.3121 0.0871 0.022 Uiso 1 1 calc R . . C10 C -0.31130(19) -0.26234(17) 0.23365(14) 0.0175(3) Uani 1 1 d . . . H4 H -0.3935 -0.3433 0.2153 0.021 Uiso 1 1 calc R . . C11 C -0.31784(19) -0.16458(17) 0.33585(14) 0.0157(3) Uani 1 1 d . . . H3 H -0.4035 -0.1765 0.3881 0.019 Uiso 1 1 calc R . . C12 C 0.28649(18) 0.00777(16) 0.00512(13) 0.0137(3) Uani 1 1 d . . . C13 C 0.32875(19) -0.07119(18) -0.10659(14) 0.0176(3) Uani 1 1 d . . . H9 H 0.3805 -0.0052 -0.1556 0.026 Uiso 1 1 calc R . . H10 H 0.2319 -0.1288 -0.1482 0.026 Uiso 1 1 calc R . . H11 H 0.4023 -0.1327 -0.0912 0.026 Uiso 1 1 calc R . . C14 C 0.2666(3) 0.6200(2) 0.05705(17) 0.0350(5) Uani 1 1 d . . . H12 H 0.3683 0.6590 0.0255 0.053 Uiso 1 1 calc R . . H13 H 0.1786 0.6482 0.0176 0.053 Uiso 1 1 calc R . . H14 H 0.2525 0.5167 0.0428 0.053 Uiso 1 1 calc R . . C15 C 0.2670(2) 0.67330(18) 0.18313(16) 0.0226(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ru1 0.00899(6) 0.01027(7) 0.00890(6) 0.00109(4) 0.00222(4) 0.00128(4) Cl1 0.01485(17) 0.01396(18) 0.01784(18) 0.00339(14) 0.00637(14) 0.00063(14) Cl2 0.01517(18) 0.02138(19) 0.01407(17) 0.00509(14) 0.00180(13) 0.00652(15) Cl3 0.01292(17) 0.01572(18) 0.01441(17) 0.00388(13) 0.00175(13) 0.00377(14) S1 0.01214(17) 0.01376(18) 0.01164(17) 0.00098(13) 0.00400(13) 0.00029(14) N1 0.0110(6) 0.0120(6) 0.0113(6) 0.0021(5) 0.0007(5) 0.0031(5) C16 0.0141(7) 0.0123(7) 0.0201(8) -0.0014(6) -0.0026(6) 0.0020(6) N3 0.0102(6) 0.0122(6) 0.0103(6) 0.0018(5) 0.0010(5) 0.0018(5) N4 0.0112(6) 0.0146(6) 0.0137(6) 0.0034(5) 0.0023(5) 0.0015(5) N5 0.0342(9) 0.0312(9) 0.0298(9) 0.0002(7) 0.0106(7) 0.0045(7) C1 0.0119(7) 0.0133(7) 0.0174(7) 0.0026(6) 0.0011(6) 0.0022(6) C2 0.0180(8) 0.0178(8) 0.0129(7) -0.0021(6) -0.0009(6) 0.0069(6) C3 0.0149(7) 0.0177(8) 0.0127(7) 0.0023(6) 0.0025(6) 0.0042(6) C4 0.0105(7) 0.0131(7) 0.0120(7) 0.0028(6) 0.0004(5) 0.0034(6) C5 0.0114(7) 0.0135(7) 0.0105(7) 0.0039(5) 0.0015(5) 0.0032(6) C6 0.0140(7) 0.0138(7) 0.0105(7) 0.0026(6) 0.0004(5) 0.0033(6) C7 0.0105(7) 0.0122(7) 0.0130(7) 0.0034(6) -0.0007(5) 0.0010(6) C8 0.0151(7) 0.0160(8) 0.0138(7) 0.0010(6) 0.0030(6) 0.0016(6) C9 0.0202(8) 0.0156(8) 0.0161(8) -0.0014(6) 0.0008(6) 0.0004(6) C10 0.0157(8) 0.0153(8) 0.0194(8) 0.0026(6) -0.0018(6) -0.0024(6) C11 0.0132(7) 0.0175(8) 0.0165(7) 0.0054(6) 0.0019(6) 0.0006(6) C12 0.0103(7) 0.0158(7) 0.0152(7) 0.0043(6) 0.0003(6) 0.0018(6) C13 0.0170(8) 0.0205(8) 0.0141(7) -0.0020(6) 0.0013(6) 0.0056(6) C14 0.0525(13) 0.0309(11) 0.0237(10) 0.0103(8) 0.0041(9) 0.0079(10) C15 0.0198(8) 0.0189(8) 0.0300(10) 0.0063(7) 0.0064(7) 0.0038(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N4 2.0494(13) . ? Ru1 N1 2.0536(12) . ? Ru1 N3 2.0769(12) . ? Ru1 Cl3 2.3273(4) . ? Ru1 Cl2 2.3485(4) . ? Ru1 Cl1 2.3554(4) . ? S1 C5 1.7190(15) . ? S1 C6 1.7384(15) . ? N1 C1 1.343(2) . ? N1 C4 1.3610(19) . ? C16 C2 1.383(2) . ? C16 C1 1.390(2) . ? C16 H1 0.9500 . ? N3 C5 1.3195(19) . ? N3 C7 1.3951(19) . ? N4 C12 1.138(2) . ? N5 C15 1.137(2) . ? C1 H8 0.9500 . ? C2 C3 1.389(2) . ? C2 H2 0.9500 . ? C3 C4 1.385(2) . ? C3 H7 0.9500 . ? C4 C5 1.454(2) . ? C6 C11 1.396(2) . ? C6 C7 1.407(2) . ? C7 C8 1.396(2) . ? C8 C9 1.381(2) . ? C8 H6 0.9500 . ? C9 C10 1.405(2) . ? C9 H5 0.9500 . ? C10 C11 1.383(2) . ? C10 H4 0.9500 . ? C11 H3 0.9500 . ? C12 C13 1.455(2) . ? C13 H9 0.9800 . ? C13 H10 0.9800 . ? C13 H11 0.9800 . ? C14 C15 1.448(3) . ? C14 H12 0.9800 . ? C14 H13 0.9800 . ? C14 H14 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 N4 Ru1 N1 179.32(5) . . ? N4 Ru1 N3 101.09(5) . . ? N1 Ru1 N3 79.15(5) . . ? N4 Ru1 Cl3 90.03(4) . . ? N1 Ru1 Cl3 89.34(3) . . ? N3 Ru1 Cl3 89.58(3) . . ? N4 Ru1 Cl2 89.64(4) . . ? N1 Ru1 Cl2 91.01(3) . . ? N3 Ru1 Cl2 86.61(3) . . ? Cl3 Ru1 Cl2 176.029(14) . . ? N4 Ru1 Cl1 85.04(4) . . ? N1 Ru1 Cl1 94.74(4) . . ? N3 Ru1 Cl1 173.54(4) . . ? Cl3 Ru1 Cl1 92.479(14) . . ? Cl2 Ru1 Cl1 91.434(14) . . ? C5 S1 C6 89.15(7) . . ? C1 N1 C4 118.44(13) . . ? C1 N1 Ru1 126.04(10) . . ? C4 N1 Ru1 115.47(10) . . ? C2 C16 C1 119.08(15) . . ? C2 C16 H1 120.5 . . ? C1 C16 H1 120.5 . . ? C5 N3 C7 111.16(12) . . ? C5 N3 Ru1 113.11(10) . . ? C7 N3 Ru1 135.47(10) . . ? C12 N4 Ru1 170.09(13) . . ? N1 C1 C16 122.17(14) . . ? N1 C1 H8 118.9 . . ? C16 C1 H8 118.9 . . ? C16 C2 C3 119.36(14) . . ? C16 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 118.68(15) . . ? C4 C3 H7 120.7 . . ? C2 C3 H7 120.7 . . ? N1 C4 C3 122.23(14) . . ? N1 C4 C5 113.16(13) . . ? C3 C4 C5 124.61(14) . . ? N3 C5 C4 118.92(13) . . ? N3 C5 S1 116.06(12) . . ? C4 C5 S1 125.02(11) . . ? C11 C6 C7 121.93(14) . . ? C11 C6 S1 127.63(12) . . ? C7 C6 S1 110.41(11) . . ? N3 C7 C8 127.04(14) . . ? N3 C7 C6 113.20(13) . . ? C8 C7 C6 119.71(14) . . ? C9 C8 C7 118.32(14) . . ? C9 C8 H6 120.8 . . ? C7 C8 H6 120.8 . . ? C8 C9 C10 121.64(15) . . ? C8 C9 H5 119.2 . . ? C10 C9 H5 119.2 . . ? C11 C10 C9 120.78(15) . . ? C11 C10 H4 119.6 . . ? C9 C10 H4 119.6 . . ? C10 C11 C6 117.63(14) . . ? C10 C11 H3 121.2 . . ? C6 C11 H3 121.2 . . ? N4 C12 C13 178.74(17) . . ? C12 C13 H9 109.5 . . ? C12 C13 H10 109.5 . . ? H9 C13 H10 109.5 . . ? C12 C13 H11 109.5 . . ? H9 C13 H11 109.5 . . ? H10 C13 H11 109.5 . . ? C15 C14 H12 109.5 . . ? C15 C14 H13 109.5 . . ? H12 C14 H13 109.5 . . ? C15 C14 H14 109.5 . . ? H12 C14 H14 109.5 . . ? H13 C14 H14 109.5 . . ? N5 C15 C14 178.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Ru1 N1 C1 178.38(13) . . . . ? Cl3 Ru1 N1 C1 88.69(12) . . . . ? Cl2 Ru1 N1 C1 -95.27(12) . . . . ? Cl1 Ru1 N1 C1 -3.75(12) . . . . ? N3 Ru1 N1 C4 0.91(10) . . . . ? Cl3 Ru1 N1 C4 -88.79(10) . . . . ? Cl2 Ru1 N1 C4 87.26(10) . . . . ? Cl1 Ru1 N1 C4 178.78(10) . . . . ? N4 Ru1 N3 C5 -178.75(10) . . . . ? N1 Ru1 N3 C5 1.89(10) . . . . ? Cl3 Ru1 N3 C5 91.30(10) . . . . ? Cl2 Ru1 N3 C5 -89.79(10) . . . . ? N4 Ru1 N3 C7 -5.28(14) . . . . ? N1 Ru1 N3 C7 175.36(14) . . . . ? Cl3 Ru1 N3 C7 -95.23(13) . . . . ? Cl2 Ru1 N3 C7 83.68(13) . . . . ? C4 N1 C1 C16 1.9(2) . . . . ? Ru1 N1 C1 C16 -175.50(11) . . . . ? C2 C16 C1 N1 -0.8(2) . . . . ? C1 C16 C2 C3 -0.9(2) . . . . ? C16 C2 C3 C4 1.3(2) . . . . ? C1 N1 C4 C3 -1.4(2) . . . . ? Ru1 N1 C4 C3 176.24(11) . . . . ? C1 N1 C4 C5 179.03(12) . . . . ? Ru1 N1 C4 C5 -3.29(15) . . . . ? C2 C3 C4 N1 -0.2(2) . . . . ? C2 C3 C4 C5 179.31(14) . . . . ? C7 N3 C5 C4 -179.48(12) . . . . ? Ru1 N3 C5 C4 -4.38(16) . . . . ? C7 N3 C5 S1 -0.67(16) . . . . ? Ru1 N3 C5 S1 174.43(7) . . . . ? N1 C4 C5 N3 5.18(19) . . . . ? C3 C4 C5 N3 -174.33(14) . . . . ? N1 C4 C5 S1 -173.51(10) . . . . ? C3 C4 C5 S1 7.0(2) . . . . ? C6 S1 C5 N3 -0.08(12) . . . . ? C6 S1 C5 C4 178.64(13) . . . . ? C5 S1 C6 C11 -177.09(14) . . . . ? C5 S1 C6 C7 0.80(11) . . . . ? C5 N3 C7 C8 178.87(14) . . . . ? Ru1 N3 C7 C8 5.3(2) . . . . ? C5 N3 C7 C6 1.29(17) . . . . ? Ru1 N3 C7 C6 -172.27(10) . . . . ? C11 C6 C7 N3 176.68(13) . . . . ? S1 C6 C7 N3 -1.34(16) . . . . ? C11 C6 C7 C8 -1.1(2) . . . . ? S1 C6 C7 C8 -179.12(11) . . . . ? N3 C7 C8 C9 -176.82(14) . . . . ? C6 C7 C8 C9 0.6(2) . . . . ? C7 C8 C9 C10 0.0(2) . . . . ? C8 C9 C10 C11 -0.1(2) . . . . ? C9 C10 C11 C6 -0.3(2) . . . . ? C7 C6 C11 C10 0.9(2) . . . . ? S1 C6 C11 C10 178.59(12) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 26.83 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.417 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 937657' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _iucr_refine_instructions_details ; TITL 1 in P-1 CELL 0.71073 8.6945 9.5982 11.3983 102.453 90.168 99.820 ZERR 2.00 0.0004 0.0004 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H N CL RU UNIT 32 30 10 6 2 MERG 2 OMIT 0 -7 4 OMIT 1 -1 1 OMIT -2 5 1 OMIT 1 -5 3 FMAP 2 PLAN 5 SIZE 0.10 0.20 0.35 ACTA BOND $H CONF WGHT 0.02570 0.53610 L.S. 4 TEMP -173.00 FVAR 0.11369 RU1 5 0.264510 0.282571 0.260407 11.00000 0.00983 0.01150 = 0.00862 0.00070 0.00239 0.00193 CL1 4 0.097426 0.391591 0.163525 11.00000 0.01464 0.01640 = 0.01321 0.00374 0.00191 0.00425 CL2 4 0.444213 0.182408 0.357725 11.00000 0.01511 0.02251 = 0.01404 0.00443 0.00214 0.00715 CL3 4 0.053776 0.132175 0.327223 11.00000 0.01464 0.01462 = 0.01749 0.00424 0.00516 0.00177 N1 3 0.283127 0.139286 0.099801 11.00000 0.01200 0.01402 = 0.01159 0.00132 0.00181 0.00346 N2 3 0.450324 0.393543 0.189267 11.00000 0.01230 0.01387 = 0.01066 0.00096 0.00174 0.00217 N3 3 0.621822 0.393716 0.045448 11.00000 0.01227 0.01671 = 0.00994 0.00088 0.00349 0.00203 AFIX 43 H2 2 0.667984 0.365283 -0.021945 11.00000 -1.20000 AFIX 0 N4 3 0.245492 0.430343 0.415600 11.00000 0.01140 0.01695 = 0.01273 0.00322 0.00139 0.00134 N5 3 0.751632 0.257812 -0.181182 11.00000 0.02514 0.02490 = 0.02302 0.00540 0.00946 0.00289 C1 1 0.187471 0.012059 0.059015 11.00000 0.01405 0.01453 = 0.01603 0.00063 0.00028 0.00219 AFIX 43 H9 2 0.108849 -0.020524 0.109452 11.00000 -1.20000 AFIX 0 C2 1 0.199710 -0.073467 -0.054498 11.00000 0.01650 0.01536 = 0.02049 -0.00153 -0.00211 0.00264 AFIX 43 H1 2 0.129996 -0.162642 -0.081297 11.00000 -1.20000 AFIX 0 C3 1 0.314293 -0.027203 -0.127645 11.00000 0.01810 0.02058 = 0.01263 -0.00388 -0.00123 0.00673 AFIX 43 H8 2 0.323367 -0.083645 -0.205933 11.00000 -1.20000 AFIX 0 C4 1 0.416512 0.102611 -0.086108 11.00000 0.01444 0.01986 = 0.01342 0.00093 0.00259 0.00437 AFIX 43 H7 2 0.497497 0.135419 -0.134623 11.00000 -1.20000 AFIX 0 C5 1 0.397481 0.183095 0.027821 11.00000 0.01143 0.01314 = 0.01236 0.00099 0.00005 0.00277 C6 1 0.491743 0.322738 0.083923 11.00000 0.01245 0.01532 = 0.01031 0.00211 0.00063 0.00422 C7 1 0.559429 0.520658 0.222165 11.00000 0.01062 0.01433 = 0.01349 0.00451 0.00032 0.00202 C8 1 0.670012 0.520604 0.132004 11.00000 0.01483 0.01527 = 0.01030 0.00374 0.00159 0.00451 C9 1 0.799893 0.630440 0.141644 11.00000 0.01486 0.02005 = 0.01435 0.00629 0.00261 0.00216 AFIX 43 H3 2 0.874969 0.629483 0.081218 11.00000 -1.20000 AFIX 0 C10 1 0.814050 0.741021 0.243680 11.00000 0.01592 0.01759 = 0.01931 0.00569 -0.00163 -0.00198 AFIX 43 H4 2 0.900753 0.818142 0.253216 11.00000 -1.20000 AFIX 0 C11 1 0.703221 0.742296 0.333884 11.00000 0.01982 0.01665 = 0.01410 -0.00041 -0.00087 0.00250 AFIX 43 H5 2 0.716955 0.820214 0.402535 11.00000 -1.20000 AFIX 0 C12 1 0.575307 0.632868 0.324603 11.00000 0.01456 0.01711 = 0.01335 0.00186 0.00190 0.00400 AFIX 43 H6 2 0.500956 0.633863 0.385553 11.00000 -1.20000 AFIX 0 C13 1 0.217868 0.500441 0.504272 11.00000 0.00972 0.01538 = 0.01592 0.00474 0.00011 0.00170 C14 1 0.179218 0.588039 0.617546 11.00000 0.01712 0.02021 = 0.01351 -0.00077 0.00315 0.00694 AFIX 137 H10 2 0.104947 0.648733 0.601933 11.00000 -1.50000 H12 2 0.274472 0.649936 0.657621 11.00000 -1.50000 H11 2 0.132209 0.524440 0.669367 11.00000 -1.50000 AFIX 0 C15 1 0.765853 0.213242 -0.282151 11.00000 0.01962 0.01904 = 0.02842 0.00753 0.00525 0.00284 C16 1 0.783317 0.156632 -0.409599 11.00000 0.04040 0.02786 = 0.02007 0.00693 0.00542 0.01383 AFIX 137 H14 2 0.782842 0.052140 -0.424024 11.00000 -1.50000 H15 2 0.882343 0.205073 -0.434567 11.00000 -1.50000 H13 2 0.696529 0.174560 -0.456037 11.00000 -1.50000 AFIX 0 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 END ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 Cl3 N4 Ru, C2 H3 N' _chemical_formula_sum 'C16 H15 Cl3 N5 Ru' _chemical_formula_weight 484.75 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6945(4) _cell_length_b 9.5982(4) _cell_length_c 11.3983(5) _cell_angle_alpha 102.453(2) _cell_angle_beta 90.168(2) _cell_angle_gamma 99.820(2) _cell_volume 914.44(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3476 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 26.6 _exptl_crystal_description planar _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 482 _exptl_absorpt_coefficient_mu 1.305 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6581 _exptl_absorpt_correction_T_max 0.8806 _exptl_absorpt_process_details 'SADABS, Bruker 2012' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\w and \f-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13906 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.56 _reflns_number_total 3697 _reflns_number_gt 3474 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX2 (Bruker, 2012)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2012)' _computing_data_reduction 'SAINT-Plus (Bruker, 2012)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material 'PublCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0257P)^2^+0.5361P] 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 3697 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0188 _refine_ls_R_factor_gt 0.0175 _refine_ls_wR_factor_ref 0.0503 _refine_ls_wR_factor_gt 0.0495 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.264515(14) 0.282575(14) 0.260405(11) 0.01025(5) Uani 1 1 d . . . Cl1 Cl 0.09745(5) 0.39160(4) 0.16354(4) 0.01459(9) Uani 1 1 d . . . Cl2 Cl 0.44422(5) 0.18241(5) 0.35771(4) 0.01678(9) Uani 1 1 d . . . Cl3 Cl 0.05379(5) 0.13220(5) 0.32720(4) 0.01561(9) Uani 1 1 d . . . N1 N 0.28314(16) 0.13921(16) 0.09984(12) 0.0126(3) Uani 1 1 d . . . N2 N 0.45028(16) 0.39370(16) 0.18937(12) 0.0126(3) Uani 1 1 d . . . N3 N 0.62190(16) 0.39371(16) 0.04541(12) 0.0133(3) Uani 1 1 d . . . H2 H 0.6681 0.3654 -0.0220 0.016 Uiso 1 1 calc R . . N4 N 0.24536(16) 0.43023(16) 0.41566(13) 0.0138(3) Uani 1 1 d . . . N5 N 0.75165(19) 0.25781(19) -0.18130(15) 0.0246(4) Uani 1 1 d . . . C1 C 0.1874(2) 0.01209(19) 0.05903(15) 0.0153(3) Uani 1 1 d . . . H9 H 0.1086 -0.0204 0.1094 0.018 Uiso 1 1 calc R . . C2 C 0.1998(2) -0.0735(2) -0.05446(16) 0.0182(4) Uani 1 1 d . . . H1 H 0.1303 -0.1628 -0.0812 0.022 Uiso 1 1 calc R . . C3 C 0.3143(2) -0.0271(2) -0.12765(16) 0.0179(4) Uani 1 1 d . . . H8 H 0.3233 -0.0834 -0.2060 0.021 Uiso 1 1 calc R . . C4 C 0.4165(2) 0.1026(2) -0.08602(15) 0.0161(3) Uani 1 1 d . . . H7 H 0.4975 0.1354 -0.1345 0.019 Uiso 1 1 calc R . . C5 C 0.39750(18) 0.18325(18) 0.02782(15) 0.0126(3) Uani 1 1 d . . . C6 C 0.49167(19) 0.32249(19) 0.08388(14) 0.0125(3) Uani 1 1 d . . . C7 C 0.55956(18) 0.52054(18) 0.22203(15) 0.0125(3) Uani 1 1 d . . . C8 C 0.66986(19) 0.52060(19) 0.13205(14) 0.0132(3) Uani 1 1 d . . . C9 C 0.7999(2) 0.6305(2) 0.14174(15) 0.0160(3) Uani 1 1 d . . . H3 H 0.8750 0.6295 0.0813 0.019 Uiso 1 1 calc R . . C10 C 0.8140(2) 0.7410(2) 0.24364(16) 0.0178(4) Uani 1 1 d . . . H4 H 0.9007 0.8181 0.2531 0.021 Uiso 1 1 calc R . . C11 C 0.7033(2) 0.7423(2) 0.33376(16) 0.0176(4) Uani 1 1 d . . . H5 H 0.7171 0.8203 0.4024 0.021 Uiso 1 1 calc R . . C12 C 0.57543(19) 0.63289(19) 0.32462(15) 0.0150(3) Uani 1 1 d . . . H6 H 0.5011 0.6339 0.3856 0.018 Uiso 1 1 calc R . . C13 C 0.21801(18) 0.50045(19) 0.50418(15) 0.0134(3) Uani 1 1 d . . . C14 C 0.1791(2) 0.5881(2) 0.61750(15) 0.0173(4) Uani 1 1 d . . . H10 H 0.1044 0.6484 0.6018 0.026 Uiso 1 1 calc R . . H12 H 0.2742 0.6504 0.6575 0.026 Uiso 1 1 calc R . . H11 H 0.1325 0.5245 0.6694 0.026 Uiso 1 1 calc R . . C15 C 0.7658(2) 0.2133(2) -0.28215(18) 0.0219(4) Uani 1 1 d . . . C16 C 0.7834(3) 0.1566(2) -0.40952(17) 0.0284(4) Uani 1 1 d . . . H14 H 0.7832 0.0521 -0.4238 0.043 Uiso 1 1 calc R . . H15 H 0.8824 0.2051 -0.4345 0.043 Uiso 1 1 calc R . . H13 H 0.6965 0.1742 -0.4560 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ru1 0.00987(8) 0.01155(8) 0.00866(8) 0.00073(5) 0.00241(5) 0.00192(5) Cl1 0.01470(19) 0.0165(2) 0.01337(19) 0.00387(15) 0.00195(15) 0.00420(15) Cl2 0.0152(2) 0.0227(2) 0.0141(2) 0.00451(16) 0.00219(15) 0.00716(16) Cl3 0.01471(19) 0.0147(2) 0.0175(2) 0.00431(16) 0.00523(15) 0.00181(15) N1 0.0121(7) 0.0139(7) 0.0115(7) 0.0014(5) 0.0017(5) 0.0035(5) N2 0.0124(7) 0.0139(7) 0.0106(6) 0.0007(5) 0.0018(5) 0.0026(5) N3 0.0122(7) 0.0166(7) 0.0100(7) 0.0009(5) 0.0034(5) 0.0020(5) N4 0.0114(7) 0.0168(8) 0.0131(7) 0.0039(6) 0.0015(5) 0.0010(6) N5 0.0250(8) 0.0248(9) 0.0235(9) 0.0056(7) 0.0097(7) 0.0027(7) C1 0.0140(8) 0.0147(9) 0.0161(8) 0.0008(7) 0.0006(6) 0.0025(6) C2 0.0161(8) 0.0153(9) 0.0205(9) -0.0019(7) -0.0021(7) 0.0027(7) C3 0.0182(9) 0.0203(9) 0.0129(8) -0.0041(7) -0.0011(7) 0.0070(7) C4 0.0145(8) 0.0197(9) 0.0135(8) 0.0008(7) 0.0024(6) 0.0045(7) C5 0.0116(8) 0.0137(8) 0.0124(8) 0.0014(6) 0.0001(6) 0.0034(6) C6 0.0123(8) 0.0158(8) 0.0098(7) 0.0023(6) 0.0007(6) 0.0043(6) C7 0.0109(7) 0.0141(8) 0.0132(8) 0.0043(6) 0.0002(6) 0.0023(6) C8 0.0148(8) 0.0155(8) 0.0103(8) 0.0037(6) 0.0011(6) 0.0043(6) C9 0.0147(8) 0.0202(9) 0.0142(8) 0.0065(7) 0.0027(6) 0.0022(7) C10 0.0158(8) 0.0173(9) 0.0192(9) 0.0056(7) -0.0016(7) -0.0023(7) C11 0.0198(9) 0.0162(9) 0.0146(8) -0.0005(7) -0.0007(7) 0.0026(7) C12 0.0147(8) 0.0166(9) 0.0134(8) 0.0016(7) 0.0019(6) 0.0041(7) C13 0.0097(8) 0.0153(8) 0.0157(8) 0.0046(7) 0.0004(6) 0.0016(6) C14 0.0174(8) 0.0200(9) 0.0136(8) -0.0011(7) 0.0033(7) 0.0070(7) C15 0.0197(9) 0.0192(10) 0.0280(11) 0.0077(8) 0.0052(8) 0.0031(7) C16 0.0413(12) 0.0279(11) 0.0198(10) 0.0069(8) 0.0054(8) 0.0142(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N4 2.0417(15) . ? Ru1 N2 2.0481(14) . ? Ru1 N1 2.0642(14) . ? Ru1 Cl1 2.3306(4) . ? Ru1 Cl2 2.3575(4) . ? Ru1 Cl3 2.3663(4) . ? N1 C1 1.343(2) . ? N1 C5 1.361(2) . ? N2 C6 1.332(2) . ? N2 C7 1.390(2) . ? N3 C6 1.345(2) . ? N3 C8 1.392(2) . ? N3 H2 0.8800 . ? N4 C13 1.136(2) . ? N5 C15 1.152(3) . ? C1 C2 1.390(2) . ? C1 H9 0.9500 . ? C2 C3 1.378(3) . ? C2 H1 0.9500 . ? C3 C4 1.389(3) . ? C3 H8 0.9500 . ? C4 C5 1.386(2) . ? C4 H7 0.9500 . ? C5 C6 1.456(2) . ? C7 C12 1.398(2) . ? C7 C8 1.406(2) . ? C8 C9 1.394(2) . ? C9 C10 1.383(3) . ? C9 H3 0.9500 . ? C10 C11 1.409(2) . ? C10 H4 0.9500 . ? C11 C12 1.380(3) . ? C11 H5 0.9500 . ? C12 H6 0.9500 . ? C13 C14 1.457(2) . ? C14 H10 0.9800 . ? C14 H12 0.9800 . ? C14 H11 0.9800 . ? C15 C16 1.455(3) . ? C16 H14 0.9800 . ? C16 H15 0.9800 . ? C16 H13 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 N4 Ru1 N2 99.90(6) . . ? N4 Ru1 N1 177.84(5) . . ? N2 Ru1 N1 78.88(6) . . ? N4 Ru1 Cl1 88.83(4) . . ? N2 Ru1 Cl1 89.06(4) . . ? N1 Ru1 Cl1 89.36(4) . . ? N4 Ru1 Cl2 90.53(4) . . ? N2 Ru1 Cl2 88.15(4) . . ? N1 Ru1 Cl2 91.21(4) . . ? Cl1 Ru1 Cl2 176.984(15) . . ? N4 Ru1 Cl3 86.00(4) . . ? N2 Ru1 Cl3 173.94(4) . . ? N1 Ru1 Cl3 95.26(4) . . ? Cl1 Ru1 Cl3 92.477(15) . . ? Cl2 Ru1 Cl3 90.419(15) . . ? C1 N1 C5 118.38(14) . . ? C1 N1 Ru1 125.50(11) . . ? C5 N1 Ru1 116.02(11) . . ? C6 N2 C7 106.58(13) . . ? C6 N2 Ru1 114.06(11) . . ? C7 N2 Ru1 139.09(11) . . ? C6 N3 C8 107.23(13) . . ? C6 N3 H2 126.4 . . ? C8 N3 H2 126.4 . . ? C13 N4 Ru1 171.21(14) . . ? N1 C1 C2 122.15(16) . . ? N1 C1 H9 118.9 . . ? C2 C1 H9 118.9 . . ? C3 C2 C1 119.15(17) . . ? C3 C2 H1 120.4 . . ? C1 C2 H1 120.4 . . ? C2 C3 C4 119.51(16) . . ? C2 C3 H8 120.2 . . ? C4 C3 H8 120.2 . . ? C5 C4 C3 118.52(16) . . ? C5 C4 H7 120.7 . . ? C3 C4 H7 120.7 . . ? N1 C5 C4 122.27(15) . . ? N1 C5 C6 112.15(14) . . ? C4 C5 C6 125.57(15) . . ? N2 C6 N3 112.11(15) . . ? N2 C6 C5 118.68(15) . . ? N3 C6 C5 129.20(15) . . ? N2 C7 C12 131.18(15) . . ? N2 C7 C8 107.94(15) . . ? C12 C7 C8 120.83(16) . . ? N3 C8 C9 131.96(15) . . ? N3 C8 C7 106.13(14) . . ? C9 C8 C7 121.86(16) . . ? C10 C9 C8 116.69(16) . . ? C10 C9 H3 121.7 . . ? C8 C9 H3 121.7 . . ? C9 C10 C11 121.78(17) . . ? C9 C10 H4 119.1 . . ? C11 C10 H4 119.1 . . ? C12 C11 C10 121.50(17) . . ? C12 C11 H5 119.2 . . ? C10 C11 H5 119.2 . . ? C11 C12 C7 117.33(15) . . ? C11 C12 H6 121.3 . . ? C7 C12 H6 121.3 . . ? N4 C13 C14 178.56(18) . . ? C13 C14 H10 109.5 . . ? C13 C14 H12 109.5 . . ? H10 C14 H12 109.5 . . ? C13 C14 H11 109.5 . . ? H10 C14 H11 109.5 . . ? H12 C14 H11 109.5 . . ? N5 C15 C16 179.8(2) . . ? C15 C16 H14 109.5 . . ? C15 C16 H15 109.5 . . ? H14 C16 H15 109.5 . . ? C15 C16 H13 109.5 . . ? H14 C16 H13 109.5 . . ? H15 C16 H13 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 N2 Ru1 N1 C1 -177.33(14) . . . . ? Cl1 Ru1 N1 C1 -88.16(13) . . . . ? Cl2 Ru1 N1 C1 94.80(13) . . . . ? Cl3 Ru1 N1 C1 4.27(13) . . . . ? N2 Ru1 N1 C5 -1.21(11) . . . . ? Cl1 Ru1 N1 C5 87.96(11) . . . . ? Cl2 Ru1 N1 C5 -89.08(11) . . . . ? Cl3 Ru1 N1 C5 -179.62(11) . . . . ? N4 Ru1 N2 C6 -179.87(11) . . . . ? N1 Ru1 N2 C6 -1.69(11) . . . . ? Cl1 Ru1 N2 C6 -91.22(11) . . . . ? Cl2 Ru1 N2 C6 89.92(11) . . . . ? N4 Ru1 N2 C7 7.17(17) . . . . ? N1 Ru1 N2 C7 -174.65(17) . . . . ? Cl1 Ru1 N2 C7 95.82(16) . . . . ? Cl2 Ru1 N2 C7 -83.05(16) . . . . ? C5 N1 C1 C2 -1.3(2) . . . . ? Ru1 N1 C1 C2 174.77(12) . . . . ? N1 C1 C2 C3 0.2(3) . . . . ? C1 C2 C3 C4 1.1(3) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? C1 N1 C5 C4 1.0(2) . . . . ? Ru1 N1 C5 C4 -175.43(12) . . . . ? C1 N1 C5 C6 180.00(14) . . . . ? Ru1 N1 C5 C6 3.59(17) . . . . ? C3 C4 C5 N1 0.3(2) . . . . ? C3 C4 C5 C6 -178.57(16) . . . . ? C7 N2 C6 N3 0.49(18) . . . . ? Ru1 N2 C6 N3 -174.71(10) . . . . ? C7 N2 C6 C5 179.50(14) . . . . ? Ru1 N2 C6 C5 4.30(19) . . . . ? C8 N3 C6 N2 0.23(18) . . . . ? C8 N3 C6 C5 -178.64(16) . . . . ? N1 C5 C6 N2 -5.2(2) . . . . ? C4 C5 C6 N2 173.74(15) . . . . ? N1 C5 C6 N3 173.56(15) . . . . ? C4 C5 C6 N3 -7.5(3) . . . . ? C6 N2 C7 C12 -178.17(17) . . . . ? Ru1 N2 C7 C12 -4.9(3) . . . . ? C6 N2 C7 C8 -1.01(18) . . . . ? Ru1 N2 C7 C8 172.29(12) . . . . ? C6 N3 C8 C9 176.57(17) . . . . ? C6 N3 C8 C7 -0.84(18) . . . . ? N2 C7 C8 N3 1.14(18) . . . . ? C12 C7 C8 N3 178.65(14) . . . . ? N2 C7 C8 C9 -176.59(14) . . . . ? C12 C7 C8 C9 0.9(2) . . . . ? N3 C8 C9 C10 -178.00(17) . . . . ? C7 C8 C9 C10 -0.9(2) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? N2 C7 C12 C11 176.52(16) . . . . ? C8 C7 C12 C11 -0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 26.56 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.434 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 937658'