data_publication_text ##=========================================================================== ##== This CIF corresponds to a manuscript being submitted to Organometallics ##=========================================================================== ##== Crystal structure deposit code CCDC 1006450 _publ_requested_journal Organometallics _publ_contact_author_name 'Pedro Valerga' _publ_contact_author_address ; Departamento de CMIM y Qu\'imica Inorg\'anica Universidad de C\'adiz Facultad de Ciencias Campus Universitario del R\'io San Pedro 11510. Puerto Real. SPAIN. ; _publ_contact_author_email pedro.valerga@uca.es _publ_contact_author_phone '34 (956) 012798' _publ_contact_author_fax '34 (956) 016288' loop_ _publ_author_name _publ_author_address 'Jim\'enez-Tenorio, Manuel' ; Departamento de CMIM y Qu\'imica Inorg\'anica Universidad de C\'adiz Facultad de Ciencias Campus Universitario del R\'io San Pedro 11510. Puerto Real. SPAIN. ; 'Puerta, M.Carmen' ; Departamento de CMIM y Qu\'imica Inorg\'anica Universidad de C\'adiz Facultad de Ciencias Campus Universitario del R\'io San Pedro 11510. Puerto Real. SPAIN. ; 'Valerga, Pedro' ; Departamento de CMIM y Qu\'imica Inorg\'anica Universidad de C\'adiz Facultad de Ciencias Campus Universitario del R\'io San Pedro 11510. Puerto Real. SPAIN. ; _publ_contact_letter ; Please consider this CIF submission for publication in Organometallics Title: Authors: Manuel Jim\'enez-Tenorio, M. Carmen Puerta and Pedro Valerga, Yours sincerely, Pedro Valerga June, 2014 ; data_pv1404 _audit_creation_method SHELXL-97 _chemical_name_systematic ; \h^2^-1,5-Cyclooctadienyl)-dichlorido-(N,N,N'-trimethylethylenediamine)- ruthenium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H26 Cl2 N2 Ru' _chemical_formula_sum 'C13 H26 Cl2 N2 Ru' _chemical_formula_weight 382.33 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.543(5) _cell_length_b 8.7306(17) _cell_length_c 14.199(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.11(3) _cell_angle_gamma 90.00 _cell_volume 3070.9(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7000 _cell_measurement_theta_min 2.775 _cell_measurement_theta_max 27.504 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 1.355 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; Bruker SMART APEX 3-circle diffractometer with CCD area detector, sealed X-ray tube, graphite monochromator. A hemisphere of the reciprocal space up to theta(max) = 27.50 deg was measured by omega scan frames with delta(omega) = 0.30 deg and 10 sec per frame, 1700 frames were recorded using program SMART (Bruker). Frame data evaluation and integration were done with program SAINT+(Bruker); Lattice parameters by least-squares refinement of the geometric parameters of the strongest reflections with program SAINT + (Bruker). Correction for absorption and crystal decay (insignificant) were applied by semi-empirical method from equivalents using program SADABS (G.M. Sheldrick, version of 2001, Univ. of Goettingen, Germany). Data reduction was done with program XPREP (BRUKER). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker SMART APEX' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '1700 omega scan frames, 0.3 deg, 10 sec' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0060 _diffrn_reflns_number 12396 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3535 _reflns_number_gt 3386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2001)' _computing_molecular_graphics 'ORTEP-3 vers. 1.08 (Faruggia, 2005)' _computing_publication_material 'SHELXTL (Sheldrick, 2001)' _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^)+(0.0210P)^2^+8.3405P] 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 3535 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0593 _refine_ls_wR_factor_gt 0.0580 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.627208(6) 0.740706(18) 0.051173(11) 0.01143(6) Uani 1 1 d . . . Cl1 Cl 0.590137(19) 0.52483(6) 0.12042(4) 0.01642(11) Uani 1 1 d . . . Cl2 Cl 0.679994(19) 0.89389(6) -0.03682(4) 0.01827(11) Uani 1 1 d . . . N1 N 0.59712(7) 0.6226(2) -0.09346(12) 0.0153(3) Uani 1 1 d . . . N2 N 0.69437(7) 0.5863(2) 0.05910(12) 0.0153(3) Uani 1 1 d . . . H2N H 0.7209 0.6448 0.0413 0.018 Uiso 1 1 calc R . . C1 C 0.57664(8) 0.9488(3) 0.02001(16) 0.0177(4) Uani 1 1 d . . . H1 H 0.5818 0.9399 -0.0438 0.021 Uiso 1 1 calc R . . C2 C 0.54765(8) 0.8358(3) 0.05369(16) 0.0174(4) Uani 1 1 d . . . H2 H 0.5326 0.7547 0.0109 0.021 Uiso 1 1 calc R . . C3 C 0.53876(9) 0.8353(3) 0.15514(16) 0.0213(5) Uani 1 1 d . . . H3A H 0.5208 0.7383 0.1653 0.026 Uiso 1 1 calc R . . H3B H 0.5142 0.9205 0.1610 0.026 Uiso 1 1 calc R . . C4 C 0.59137(9) 0.8520(3) 0.23552(16) 0.0217(5) Uani 1 1 d . . . H4A H 0.5957 0.9608 0.2555 0.026 Uiso 1 1 calc R . . H4B H 0.5878 0.7916 0.2927 0.026 Uiso 1 1 calc R . . C5 C 0.64204(9) 0.8005(3) 0.20643(15) 0.0181(4) Uani 1 1 d . . . H5 H 0.6532 0.6969 0.2177 0.022 Uiso 1 1 calc R . . C6 C 0.67280(9) 0.8973(3) 0.16428(15) 0.0190(4) Uani 1 1 d . . . H6 H 0.7043 0.8571 0.1489 0.023 Uiso 1 1 calc R . . C7 C 0.65881(9) 1.0639(3) 0.14158(17) 0.0230(5) Uani 1 1 d . . . H7A H 0.6840 1.1070 0.1054 0.028 Uiso 1 1 calc R . . H7B H 0.6638 1.1214 0.2032 0.028 Uiso 1 1 calc R . . C8 C 0.60043(9) 1.0866(3) 0.08123(18) 0.0235(5) Uani 1 1 d . . . H8A H 0.5773 1.1113 0.1259 0.028 Uiso 1 1 calc R . . H8B H 0.5996 1.1757 0.0377 0.028 Uiso 1 1 calc R . . C9 C 0.64659(8) 0.5468(3) -0.11047(15) 0.0180(4) Uani 1 1 d . . . H9A H 0.6696 0.6241 -0.1318 0.022 Uiso 1 1 calc R . . H9B H 0.6360 0.4695 -0.1627 0.022 Uiso 1 1 calc R . . C10 C 0.67821(9) 0.4699(3) -0.01855(16) 0.0197(4) Uani 1 1 d . . . H10A H 0.6557 0.3903 0.0020 0.024 Uiso 1 1 calc R . . H10B H 0.7107 0.4198 -0.0307 0.024 Uiso 1 1 calc R . . C11 C 0.57555(9) 0.7306(3) -0.17483(16) 0.0205(5) Uani 1 1 d . . . H11A H 0.5692 0.6754 -0.2367 0.031 Uiso 1 1 calc R . . H11B H 0.6017 0.8129 -0.1741 0.031 Uiso 1 1 calc R . . H11C H 0.5415 0.7745 -0.1673 0.031 Uiso 1 1 calc R . . C12 C 0.55437(9) 0.5039(3) -0.10090(16) 0.0202(4) Uani 1 1 d . . . H12A H 0.5226 0.5497 -0.0847 0.030 Uiso 1 1 calc R . . H12B H 0.5681 0.4202 -0.0556 0.030 Uiso 1 1 calc R . . H12C H 0.5443 0.4637 -0.1673 0.030 Uiso 1 1 calc R . . C13 C 0.72179(9) 0.5121(3) 0.15191(16) 0.0214(5) Uani 1 1 d . . . H13A H 0.6958 0.4490 0.1752 0.032 Uiso 1 1 calc R . . H13B H 0.7365 0.5909 0.2003 0.032 Uiso 1 1 calc R . . H13C H 0.7512 0.4473 0.1416 0.032 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 0.00941(9) 0.01237(10) 0.01215(9) 0.00094(6) 0.00195(6) -0.00131(5) Cl1 0.0163(2) 0.0162(2) 0.0177(2) 0.00218(18) 0.00589(18) -0.00292(18) Cl2 0.0150(2) 0.0181(3) 0.0224(2) 0.00526(19) 0.00601(18) -0.00217(18) N1 0.0143(8) 0.0166(9) 0.0146(8) 0.0004(7) 0.0027(6) 0.0002(7) N2 0.0120(8) 0.0164(9) 0.0170(8) 0.0030(7) 0.0029(6) 0.0007(7) C1 0.0157(9) 0.0167(10) 0.0201(10) 0.0012(8) 0.0029(8) 0.0040(8) C2 0.0129(9) 0.0171(11) 0.0221(10) -0.0014(8) 0.0038(8) 0.0034(8) C3 0.0213(11) 0.0206(11) 0.0243(11) -0.0015(9) 0.0101(9) 0.0023(9) C4 0.0263(11) 0.0202(11) 0.0203(10) -0.0043(9) 0.0090(9) -0.0003(9) C5 0.0206(10) 0.0195(11) 0.0126(9) -0.0031(8) 0.0006(8) -0.0010(9) C6 0.0179(10) 0.0199(11) 0.0176(10) -0.0045(8) 0.0015(8) -0.0032(8) C7 0.0237(11) 0.0171(11) 0.0266(11) -0.0036(9) 0.0031(9) -0.0060(9) C8 0.0252(11) 0.0145(11) 0.0300(12) -0.0010(9) 0.0055(9) -0.0004(9) C9 0.0188(10) 0.0194(11) 0.0169(10) -0.0025(8) 0.0063(8) 0.0006(8) C10 0.0173(10) 0.0195(11) 0.0230(10) -0.0003(9) 0.0063(8) 0.0006(8) C11 0.0217(11) 0.0232(12) 0.0149(10) 0.0028(8) 0.0015(8) 0.0003(9) C12 0.0201(10) 0.0203(11) 0.0191(10) -0.0023(9) 0.0026(8) -0.0071(9) C13 0.0175(10) 0.0254(12) 0.0200(10) 0.0081(9) 0.0018(8) 0.0032(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru1 N2 2.1629(17) . ? Ru1 C2 2.204(2) . ? Ru1 C5 2.207(2) . ? Ru1 C1 2.211(2) . ? Ru1 C6 2.212(2) . ? Ru1 N1 2.2588(18) . ? Ru1 Cl1 2.4227(6) . ? Ru1 Cl2 2.4473(7) . ? N1 C11 1.489(3) . ? N1 C12 1.490(3) . ? N1 C9 1.497(3) . ? N2 C13 1.482(3) . ? N2 C10 1.483(3) . ? N2 H2N 0.9300 . ? C1 C2 1.387(3) . ? C1 C8 1.522(3) . ? C1 H1 0.9500 . ? C2 C3 1.512(3) . ? C2 H2 0.9500 . ? C3 C4 1.543(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.519(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.514(3) . ? C6 H6 0.9500 . ? C7 C8 1.541(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.514(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? 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 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ru1 C2 163.11(8) . . ? N2 Ru1 C5 98.90(8) . . ? C2 Ru1 C5 80.16(8) . . ? N2 Ru1 C1 160.03(8) . . ? C2 Ru1 C1 36.62(8) . . ? C5 Ru1 C1 87.43(8) . . ? N2 Ru1 C6 94.41(8) . . ? C2 Ru1 C6 94.58(8) . . ? C5 Ru1 C6 36.54(8) . . ? C1 Ru1 C6 79.39(8) . . ? N2 Ru1 N1 81.52(7) . . ? C2 Ru1 N1 94.36(8) . . ? C5 Ru1 N1 162.53(8) . . ? C1 Ru1 N1 98.08(7) . . ? C6 Ru1 N1 160.82(7) . . ? N2 Ru1 Cl1 82.98(5) . . ? C2 Ru1 Cl1 80.40(6) . . ? C5 Ru1 Cl1 76.56(6) . . ? C1 Ru1 Cl1 116.97(6) . . ? C6 Ru1 Cl1 112.02(6) . . ? N1 Ru1 Cl1 86.21(5) . . ? N2 Ru1 Cl2 80.69(5) . . ? C2 Ru1 Cl2 115.31(6) . . ? C5 Ru1 Cl2 113.52(6) . . ? C1 Ru1 Cl2 79.42(6) . . ? C6 Ru1 Cl2 76.99(6) . . ? N1 Ru1 Cl2 83.85(5) . . ? Cl1 Ru1 Cl2 161.958(19) . . ? C11 N1 C12 105.01(16) . . ? C11 N1 C9 108.79(16) . . ? C12 N1 C9 108.28(17) . . ? C11 N1 Ru1 113.33(13) . . ? C12 N1 Ru1 117.58(13) . . ? C9 N1 Ru1 103.60(12) . . ? C13 N2 C10 110.29(17) . . ? C13 N2 Ru1 121.04(14) . . ? C10 N2 Ru1 108.37(12) . . ? C13 N2 H2N 105.3 . . ? C10 N2 H2N 105.3 . . ? Ru1 N2 H2N 105.3 . . ? C2 C1 C8 122.6(2) . . ? C2 C1 Ru1 71.41(12) . . ? C8 C1 Ru1 113.77(14) . . ? C2 C1 H1 118.7 . . ? C8 C1 H1 118.7 . . ? Ru1 C1 H1 85.0 . . ? C1 C2 C3 123.2(2) . . ? C1 C2 Ru1 71.97(12) . . ? C3 C2 Ru1 111.57(14) . . ? C1 C2 H2 118.4 . . ? C3 C2 H2 118.4 . . ? Ru1 C2 H2 86.5 . . ? C2 C3 C4 113.48(18) . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C5 C4 C3 114.64(18) . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 123.2(2) . . ? C6 C5 Ru1 71.94(12) . . ? C4 C5 Ru1 113.05(14) . . ? C6 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? Ru1 C5 H5 85.1 . . ? C5 C6 C7 123.3(2) . . ? C5 C6 Ru1 71.51(12) . . ? C7 C6 Ru1 112.59(14) . . ? C5 C6 H6 118.4 . . ? C7 C6 H6 118.4 . . ? Ru1 C6 H6 86.0 . . ? C6 C7 C8 112.86(18) . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C1 C8 C7 114.43(19) . . ? C1 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? C1 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? N1 C9 C10 110.54(17) . . ? N1 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N2 C10 C9 109.29(18) . . ? N2 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? N2 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? 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 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C11 -134.11(15) . . . . ? C2 Ru1 N1 C11 62.38(15) . . . . ? C5 Ru1 N1 C11 133.2(2) . . . . ? C1 Ru1 N1 C11 25.72(15) . . . . ? C6 Ru1 N1 C11 -55.2(3) . . . . ? Cl1 Ru1 N1 C11 142.44(14) . . . . ? Cl2 Ru1 N1 C11 -52.64(13) . . . . ? N2 Ru1 N1 C12 102.98(15) . . . . ? C2 Ru1 N1 C12 -60.53(16) . . . . ? C5 Ru1 N1 C12 10.3(3) . . . . ? C1 Ru1 N1 C12 -97.20(15) . . . . ? C6 Ru1 N1 C12 -178.1(2) . . . . ? Cl1 Ru1 N1 C12 19.52(14) . . . . ? Cl2 Ru1 N1 C12 -175.56(15) . . . . ? N2 Ru1 N1 C9 -16.38(12) . . . . ? C2 Ru1 N1 C9 -179.89(13) . . . . ? C5 Ru1 N1 C9 -109.1(3) . . . . ? C1 Ru1 N1 C9 143.44(13) . . . . ? C6 Ru1 N1 C9 62.5(3) . . . . ? Cl1 Ru1 N1 C9 -99.84(12) . . . . ? Cl2 Ru1 N1 C9 65.08(12) . . . . ? C2 Ru1 N2 C13 -65.0(3) . . . . ? C5 Ru1 N2 C13 20.42(17) . . . . ? C1 Ru1 N2 C13 127.8(2) . . . . ? C6 Ru1 N2 C13 56.95(17) . . . . ? N1 Ru1 N2 C13 -141.91(16) . . . . ? Cl1 Ru1 N2 C13 -54.72(15) . . . . ? Cl2 Ru1 N2 C13 132.98(16) . . . . ? C2 Ru1 N2 C10 63.8(3) . . . . ? C5 Ru1 N2 C10 149.20(14) . . . . ? C1 Ru1 N2 C10 -103.5(2) . . . . ? C6 Ru1 N2 C10 -174.27(14) . . . . ? N1 Ru1 N2 C10 -13.13(13) . . . . ? Cl1 Ru1 N2 C10 74.06(13) . . . . ? Cl2 Ru1 N2 C10 -98.24(13) . . . . ? N2 Ru1 C1 C2 173.83(18) . . . . ? C5 Ru1 C1 C2 -76.91(14) . . . . ? C6 Ru1 C1 C2 -112.84(14) . . . . ? N1 Ru1 C1 C2 86.43(13) . . . . ? Cl1 Ru1 C1 C2 -3.41(14) . . . . ? Cl2 Ru1 C1 C2 168.58(13) . . . . ? N2 Ru1 C1 C8 -68.0(3) . . . . ? C2 Ru1 C1 C8 118.2(2) . . . . ? C5 Ru1 C1 C8 41.27(17) . . . . ? C6 Ru1 C1 C8 5.34(16) . . . . ? N1 Ru1 C1 C8 -155.39(16) . . . . ? Cl1 Ru1 C1 C8 114.77(15) . . . . ? Cl2 Ru1 C1 C8 -73.23(15) . . . . ? C8 C1 C2 C3 -2.4(3) . . . . ? Ru1 C1 C2 C3 104.4(2) . . . . ? C8 C1 C2 Ru1 -106.84(19) . . . . ? N2 Ru1 C2 C1 -172.7(2) . . . . ? C5 Ru1 C2 C1 99.04(14) . . . . ? C6 Ru1 C2 C1 65.33(14) . . . . ? N1 Ru1 C2 C1 -97.68(13) . . . . ? Cl1 Ru1 C2 C1 176.92(13) . . . . ? Cl2 Ru1 C2 C1 -12.43(14) . . . . ? N2 Ru1 C2 C3 67.9(3) . . . . ? C5 Ru1 C2 C3 -20.32(16) . . . . ? C1 Ru1 C2 C3 -119.4(2) . . . . ? C6 Ru1 C2 C3 -54.02(16) . . . . ? N1 Ru1 C2 C3 142.97(15) . . . . ? Cl1 Ru1 C2 C3 57.57(15) . . . . ? Cl2 Ru1 C2 C3 -131.78(14) . . . . ? C1 C2 C3 C4 -52.1(3) . . . . ? Ru1 C2 C3 C4 29.9(2) . . . . ? C2 C3 C4 C5 -24.3(3) . . . . ? C3 C4 C5 C6 89.5(3) . . . . ? C3 C4 C5 Ru1 6.6(2) . . . . ? N2 Ru1 C5 C6 85.37(14) . . . . ? C2 Ru1 C5 C6 -111.72(14) . . . . ? C1 Ru1 C5 C6 -75.58(14) . . . . ? N1 Ru1 C5 C6 175.4(2) . . . . ? Cl1 Ru1 C5 C6 165.89(14) . . . . ? Cl2 Ru1 C5 C6 1.71(15) . . . . ? N2 Ru1 C5 C4 -155.47(16) . . . . ? C2 Ru1 C5 C4 7.43(16) . . . . ? C1 Ru1 C5 C4 43.57(17) . . . . ? C6 Ru1 C5 C4 119.2(2) . . . . ? N1 Ru1 C5 C4 -65.4(3) . . . . ? Cl1 Ru1 C5 C4 -74.95(15) . . . . ? Cl2 Ru1 C5 C4 120.86(15) . . . . ? C4 C5 C6 C7 -0.8(3) . . . . ? Ru1 C5 C6 C7 105.4(2) . . . . ? C4 C5 C6 Ru1 -106.18(19) . . . . ? N2 Ru1 C6 C5 -99.01(14) . . . . ? C2 Ru1 C6 C5 66.67(14) . . . . ? C1 Ru1 C6 C5 100.14(14) . . . . ? N1 Ru1 C6 C5 -175.80(19) . . . . ? Cl1 Ru1 C6 C5 -14.82(14) . . . . ? Cl2 Ru1 C6 C5 -178.39(14) . . . . ? N2 Ru1 C6 C7 141.80(16) . . . . ? C2 Ru1 C6 C7 -52.52(17) . . . . ? C5 Ru1 C6 C7 -119.2(2) . . . . ? C1 Ru1 C6 C7 -19.05(16) . . . . ? N1 Ru1 C6 C7 65.0(3) . . . . ? Cl1 Ru1 C6 C7 -134.01(14) . . . . ? Cl2 Ru1 C6 C7 62.42(15) . . . . ? C5 C6 C7 C8 -52.6(3) . . . . ? Ru1 C6 C7 C8 29.5(2) . . . . ? C2 C1 C8 C7 91.5(3) . . . . ? Ru1 C1 C8 C7 9.1(3) . . . . ? C6 C7 C8 C1 -25.4(3) . . . . ? C11 N1 C9 C10 164.76(18) . . . . ? C12 N1 C9 C10 -81.6(2) . . . . ? Ru1 N1 C9 C10 43.92(19) . . . . ? C13 N2 C10 C9 175.71(17) . . . . ? Ru1 N2 C10 C9 41.12(19) . . . . ? N1 C9 C10 N2 -59.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.504 _refine_diff_density_min -0.749 _refine_diff_density_rms 0.103