# Electronic Supplementary Material (ESI) for CrystEngComm # 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_1alfa _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 Cl2 N2 O Ru' _chemical_formula_weight 442.34 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 25.574(2) _cell_length_b 8.7383(8) _cell_length_c 18.346(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.964(1) _cell_angle_gamma 90.00 _cell_volume 3654.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 800 _cell_measurement_theta_min 4 _cell_measurement_theta_max 18 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 1.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.725766 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type diffractometer _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17802 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.41 _reflns_number_total 3740 _reflns_number_gt 2700 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+29.8301P] 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 3740 _refine_ls_number_parameters 227 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.205 _refine_ls_restrained_S_all 1.205 _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 0.182605(18) 0.51028(5) 0.14774(2) 0.03384(14) Uani 1 1 d . . . Cl1 Cl 0.28600(6) 0.52060(19) 0.18081(9) 0.0482(4) Uani 1 1 d . . . Cl2 Cl 0.21283(6) 0.53211(17) 0.29142(8) 0.0452(3) Uani 1 1 d . . . N1 N 0.1910(3) 0.7569(6) 0.1589(3) 0.0427(12) Uani 1 1 d . . . N2 N 0.0792(3) 1.1112(8) -0.1869(4) 0.0651(17) Uani 1 1 d D . . O1 O 0.0117(2) 1.1531(6) -0.1428(3) 0.0632(13) Uani 1 1 d . . . C1 C 0.1851(4) 0.4301(11) -0.0300(5) 0.086(3) Uani 1 1 d . . . H1A H 0.1663 0.3629 -0.0761 0.130 Uiso 1 1 calc R . . H1B H 0.2261 0.4048 -0.0011 0.130 Uiso 1 1 calc R . . H1C H 0.1809 0.5340 -0.0488 0.130 Uiso 1 1 calc R . . C2 C 0.1574(3) 0.4120(8) 0.0260(4) 0.0543(17) Uani 1 1 d . . . C3 C 0.1755(3) 0.2949(7) 0.0858(4) 0.0448(14) Uani 1 1 d . . . H3 H 0.2050 0.2277 0.0902 0.054 Uiso 1 1 calc R . . C4 C 0.1500(3) 0.2784(6) 0.1385(3) 0.0422(13) Uani 1 1 d . . . H4 H 0.1618 0.1985 0.1761 0.051 Uiso 1 1 calc R . . C5 C 0.1064(3) 0.3815(7) 0.1355(4) 0.0437(14) Uani 1 1 d . . . C6 C 0.0885(2) 0.5000(7) 0.0771(4) 0.0548(17) Uani 1 1 d . . . H6 H 0.0602 0.5699 0.0742 0.066 Uiso 1 1 calc R . . C7 C 0.1138(3) 0.5124(8) 0.0227(4) 0.0547(17) Uani 1 1 d . . . H7 H 0.1010 0.5897 -0.0164 0.066 Uiso 1 1 calc R . . C8 C 0.0818(3) 0.3605(8) 0.1951(5) 0.0621(19) Uani 1 1 d . . . H8 H 0.1135 0.3216 0.2461 0.074 Uiso 1 1 calc R . . C9 C 0.0343(4) 0.2368(11) 0.1615(7) 0.101(3) Uani 1 1 d . . . H9A H 0.0015 0.2741 0.1131 0.151 Uiso 1 1 calc R . . H9B H 0.0216 0.2119 0.2020 0.151 Uiso 1 1 calc R . . H9C H 0.0499 0.1470 0.1484 0.151 Uiso 1 1 calc R . . C10 C 0.0593(4) 0.5049(11) 0.2150(6) 0.093(3) Uani 1 1 d . . . H10A H 0.0892 0.5821 0.2321 0.140 Uiso 1 1 calc R . . H10B H 0.0489 0.4855 0.2583 0.140 Uiso 1 1 calc R . . H10C H 0.0253 0.5396 0.1674 0.140 Uiso 1 1 calc R . . C11 C 0.1588(3) 0.8479(6) 0.0875(3) 0.0377(12) Uani 1 1 d . . . C12 C 0.1806(3) 0.8657(7) 0.0320(4) 0.0446(14) Uani 1 1 d . . . H12 H 0.2165 0.8224 0.0422 0.054 Uiso 1 1 calc R . . C13 C 0.1494(3) 0.9476(7) -0.0386(3) 0.0437(14) Uani 1 1 d . . . H13 H 0.1646 0.9595 -0.0757 0.052 Uiso 1 1 calc R . . C14 C 0.0962(2) 1.0120(6) -0.0549(3) 0.0360(11) Uani 1 1 d . . . C15 C 0.0756(2) 0.9961(7) 0.0027(3) 0.0400(12) Uani 1 1 d . . . H15 H 0.0405 1.0429 -0.0063 0.048 Uiso 1 1 calc R . . C16 C 0.1059(3) 0.9127(7) 0.0728(3) 0.0415(13) Uani 1 1 d . . . H16 H 0.0908 0.9002 0.1100 0.050 Uiso 1 1 calc R . . C17 C 0.0589(3) 1.0983(7) -0.1321(4) 0.0474(15) Uani 1 1 d . . . H1N2 H 0.182(2) 0.781(6) 0.195(4) 0.030(16) Uiso 1 1 d . . . H1N1 H 0.228(4) 0.766(9) 0.171(5) 0.07(3) Uiso 1 1 d . . . H2N1 H 0.054(3) 1.158(9) -0.232(3) 0.10(3) Uiso 1 1 d D . . H2N2 H 0.113(3) 1.080(14) -0.187(8) 0.17(5) Uiso 1 1 d 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 0.0356(2) 0.0301(2) 0.0303(2) 0.00160(18) 0.01006(16) -0.00301(19) Cl1 0.0410(7) 0.0586(9) 0.0470(8) -0.0100(7) 0.0217(6) -0.0083(7) Cl2 0.0487(8) 0.0538(9) 0.0291(6) 0.0024(6) 0.0143(6) 0.0006(7) N1 0.055(4) 0.038(3) 0.031(3) 0.001(2) 0.016(3) -0.004(2) N2 0.057(4) 0.087(5) 0.041(3) 0.023(3) 0.014(3) 0.004(3) O1 0.057(3) 0.072(3) 0.044(3) 0.009(2) 0.009(2) 0.018(3) C1 0.117(7) 0.103(7) 0.050(4) -0.019(4) 0.047(5) -0.046(6) C2 0.060(4) 0.054(4) 0.038(3) -0.008(3) 0.013(3) -0.016(3) C3 0.047(4) 0.039(3) 0.045(3) -0.011(3) 0.018(3) -0.008(3) C4 0.047(3) 0.029(3) 0.042(3) -0.001(2) 0.013(3) -0.006(2) C5 0.041(3) 0.035(3) 0.051(3) -0.002(3) 0.016(3) -0.004(2) C6 0.028(3) 0.040(3) 0.067(4) 0.004(3) -0.004(3) 0.000(3) C7 0.054(4) 0.047(4) 0.036(3) 0.008(3) -0.003(3) -0.020(3) C8 0.060(4) 0.055(4) 0.081(5) -0.011(4) 0.041(4) -0.013(3) C9 0.106(8) 0.092(7) 0.140(9) -0.031(6) 0.086(7) -0.048(6) C10 0.089(6) 0.086(6) 0.139(8) -0.029(6) 0.081(6) -0.011(5) C11 0.046(3) 0.031(3) 0.032(3) -0.001(2) 0.013(2) -0.005(2) C12 0.042(3) 0.049(3) 0.044(3) 0.007(3) 0.020(3) 0.006(3) C13 0.043(3) 0.054(3) 0.038(3) 0.010(3) 0.022(3) 0.000(3) C14 0.032(3) 0.035(3) 0.033(2) 0.000(2) 0.007(2) -0.005(2) C15 0.033(3) 0.042(3) 0.042(3) -0.001(3) 0.014(2) 0.000(3) C16 0.051(4) 0.041(3) 0.039(3) -0.001(2) 0.026(3) -0.002(3) C17 0.050(4) 0.044(3) 0.035(3) 0.001(3) 0.008(3) -0.004(3) _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 C6 2.156(5) . ? Ru1 C3 2.163(6) . ? Ru1 N1 2.166(5) . ? Ru1 C7 2.168(5) . ? Ru1 C4 2.168(5) . ? Ru1 C5 2.172(6) . ? Ru1 C2 2.200(6) . ? Ru1 Cl2 2.3947(14) . ? Ru1 Cl1 2.4319(15) . ? N1 C11 1.431(7) . ? N1 H1N2 0.81(6) . ? N1 H1N1 0.86(8) . ? N2 C17 1.328(9) . ? N2 H2N1 0.89(2) . ? N2 H2N2 0.90(2) . ? O1 C17 1.228(8) . ? C1 C2 1.498(10) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C7 1.398(10) . ? C2 C3 1.416(9) . ? C3 C4 1.399(8) . ? C3 H3 0.9300 . ? C4 C5 1.414(8) . ? C4 H4 0.9300 . ? C5 C6 1.409(8) . ? C5 C8 1.500(9) . ? C6 C7 1.419(9) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C10 1.500(10) . ? C8 C9 1.532(10) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.374(8) . ? C11 C16 1.376(8) . ? C12 C13 1.374(8) . ? C12 H12 0.9300 . ? C13 C14 1.375(8) . ? C13 H13 0.9300 . ? C14 C15 1.386(7) . ? C14 C17 1.503(8) . ? C15 C16 1.371(8) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 C6 Ru1 C3 81.0(2) . . ? C6 Ru1 N1 97.7(2) . . ? C3 Ru1 N1 153.7(2) . . ? C6 Ru1 C7 38.3(3) . . ? C3 Ru1 C7 67.5(3) . . ? N1 Ru1 C7 95.1(2) . . ? C6 Ru1 C4 68.2(2) . . ? C3 Ru1 C4 37.7(2) . . ? N1 Ru1 C4 162.8(2) . . ? C7 Ru1 C4 80.0(2) . . ? C6 Ru1 C5 38.0(2) . . ? C3 Ru1 C5 68.7(2) . . ? N1 Ru1 C5 124.9(2) . . ? C7 Ru1 C5 68.6(2) . . ? C4 Ru1 C5 38.0(2) . . ? C6 Ru1 C2 68.9(3) . . ? C3 Ru1 C2 37.9(2) . . ? N1 Ru1 C2 117.1(2) . . ? C7 Ru1 C2 37.3(3) . . ? C4 Ru1 C2 68.3(2) . . ? C5 Ru1 C2 81.8(2) . . ? C6 Ru1 Cl2 112.4(2) . . ? C3 Ru1 Cl2 123.76(17) . . ? N1 Ru1 Cl2 81.27(14) . . ? C7 Ru1 Cl2 150.1(2) . . ? C4 Ru1 Cl2 94.64(16) . . ? C5 Ru1 Cl2 88.96(17) . . ? C2 Ru1 Cl2 161.58(18) . . ? C6 Ru1 Cl1 160.4(2) . . ? C3 Ru1 Cl1 89.18(17) . . ? N1 Ru1 Cl1 83.63(18) . . ? C7 Ru1 Cl1 122.2(2) . . ? C4 Ru1 Cl1 112.99(17) . . ? C5 Ru1 Cl1 150.25(16) . . ? C2 Ru1 Cl1 93.0(2) . . ? Cl2 Ru1 Cl1 87.18(5) . . ? C11 N1 Ru1 118.4(4) . . ? C11 N1 H1N2 110(4) . . ? Ru1 N1 H1N2 106(4) . . ? C11 N1 H1N1 107(5) . . ? Ru1 N1 H1N1 100(5) . . ? H1N2 N1 H1N1 115(6) . . ? C17 N2 H2N1 113(6) . . ? C17 N2 H2N2 133(8) . . ? H2N1 N2 H2N2 114(9) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 C3 117.5(6) . . ? C7 C2 C1 121.3(7) . . ? C3 C2 C1 121.2(7) . . ? C7 C2 Ru1 70.1(4) . . ? C3 C2 Ru1 69.7(3) . . ? C1 C2 Ru1 130.0(5) . . ? C4 C3 C2 121.3(6) . . ? C4 C3 Ru1 71.4(3) . . ? C2 C3 Ru1 72.5(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? Ru1 C3 H3 129.3 . . ? C3 C4 C5 120.9(6) . . ? C3 C4 Ru1 71.0(3) . . ? C5 C4 Ru1 71.1(3) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? Ru1 C4 H4 131.2 . . ? C6 C5 C4 118.4(6) . . ? C6 C5 C8 123.1(6) . . ? C4 C5 C8 118.5(6) . . ? C6 C5 Ru1 70.4(3) . . ? C4 C5 Ru1 70.8(3) . . ? C8 C5 Ru1 129.9(4) . . ? C5 C6 C7 119.8(6) . . ? C5 C6 Ru1 71.6(3) . . ? C7 C6 Ru1 71.3(3) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? Ru1 C6 H6 129.4 . . ? C2 C7 C6 122.0(6) . . ? C2 C7 Ru1 72.6(3) . . ? C6 C7 Ru1 70.4(3) . . ? C2 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? Ru1 C7 H7 130.9 . . ? C10 C8 C5 114.1(6) . . ? C10 C8 C9 111.7(7) . . ? C5 C8 C9 108.2(6) . . ? C10 C8 H8 107.5 . . ? C5 C8 H8 107.5 . . ? C9 C8 H8 107.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 120.1(5) . . ? C12 C11 N1 118.8(6) . . ? C16 C11 N1 121.1(6) . . ? C13 C12 C11 120.0(6) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.9(5) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C15 118.3(5) . . ? C13 C14 C17 123.7(5) . . ? C15 C14 C17 118.0(5) . . ? C16 C15 C14 121.3(5) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 119.4(5) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? O1 C17 N2 122.6(6) . . ? O1 C17 C14 120.3(6) . . ? N2 C17 C14 117.1(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.458 _refine_diff_density_min -0.870 _refine_diff_density_rms 0.117 _database_code_depnum_ccdc_archive 'CCDC 941876' ####################################################################### # # 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_1beta _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 Cl2 N2 O Ru' _chemical_formula_weight 442.34 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.723(9) _cell_length_b 9.227(9) _cell_length_c 12.620(10) _cell_angle_alpha 74.260(10) _cell_angle_beta 69.800(10) _cell_angle_gamma 89.740(10) _cell_volume 913.0(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 700 _cell_measurement_theta_min 2 _cell_measurement_theta_max 22 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.482310 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type diffractometer _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4107 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_sigmaI/netI 0.1003 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 18.93 _reflns_number_total 2816 _reflns_number_gt 2038 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The structural determination of 1beta has been carried out in the P1 space group, with two independent molecules in the cell, related almost perfectly by a pseudo binary screw axis. The triclinic cell could be transformed to a centered monoclinic one, where the two fold axis could have been a proper symmetry element, with dimensions related to half the cell of 1alpha (1beta transformed to I-centered: a=9.227, b= 8.723, c=22.817 Ang, alpha=89.876, beta=96.087, gamma=90.260 deg), but no consistent space group was identified for the centered monoclinic setting. The final best model presents some problematic close contact involving terminal methyl groups, due to poor data quality. ; _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(3) _refine_ls_number_reflns 2816 _refine_ls_number_parameters 167 _refine_ls_number_restraints 74 _refine_ls_R_factor_all 0.1761 _refine_ls_R_factor_gt 0.1265 _refine_ls_wR_factor_ref 0.3864 _refine_ls_wR_factor_gt 0.3327 _refine_ls_goodness_of_fit_ref 1.500 _refine_ls_restrained_S_all 1.494 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 0.3194(4) 0.4309(4) 0.8592(3) 0.0397(17) Uani 1 1 d U . . Cl1 Cl 0.2128(17) 0.2912(18) 1.0692(14) 0.043(4) Uani 1 1 d U . . Cl2 Cl 0.296(3) 0.650(2) 0.9179(16) 0.076(7) Uani 1 1 d DU . . N1 N 0.577(5) 0.448(5) 0.864(4) 0.058(12) Uiso 1 1 d U . . H1A H 0.6198 0.5452 0.8286 0.070 Uiso 1 1 calc R . . H1B H 0.5670 0.4282 0.9404 0.070 Uiso 1 1 calc R . . O1 O 1.158(5) 0.191(5) 0.514(4) 0.095(13) Uiso 1 1 d U . . N2 N 1.027(6) -0.041(5) 0.659(4) 0.082(15) Uiso 1 1 d U . . H2A H 1.0963 -0.0922 0.6205 0.098 Uiso 1 1 calc R . . H2B H 0.9497 -0.0875 0.7239 0.098 Uiso 1 1 calc R . . C1 C 0.279(6) 0.081(3) 0.867(5) 0.10(2) Uiso 1 1 d DU . . H1C H 0.2502 0.0642 0.9506 0.143 Uiso 1 1 calc . . . H1D H 0.3869 0.0521 0.8347 0.143 Uiso 1 1 calc . . . H1E H 0.2012 0.0227 0.8533 0.143 Uiso 1 1 calc . . . C2 C 0.276(3) 0.249(2) 0.809(2) 0.031(11) Uiso 1 1 d GDU . . C3 C 0.137(3) 0.323(3) 0.848(3) 0.105(19) Uiso 1 1 d GDU . . H3 H 0.0420 0.2688 0.9061 0.126 Uiso 1 1 calc R . . C4 C 0.141(3) 0.478(3) 0.799(3) 0.091(17) Uiso 1 1 d GU . . H4 H 0.0482 0.5274 0.8249 0.110 Uiso 1 1 calc R . . C5 C 0.283(4) 0.559(2) 0.712(3) 0.055(13) Uiso 1 1 d GDU . . C6 C 0.422(3) 0.485(3) 0.673(2) 0.056(17) Uiso 1 1 d GU . . H6 H 0.5174 0.5392 0.6147 0.068 Uiso 1 1 calc R . . C7 C 0.418(3) 0.330(3) 0.722(2) 0.027(11) Uiso 1 1 d GDU . . H7 H 0.5112 0.2806 0.6959 0.032 Uiso 1 1 calc R . . C8 C 0.278(5) 0.728(3) 0.666(5) 0.092(18) Uiso 1 1 d DU . . H8 H 0.2473 0.7438 0.5957 0.111 Uiso 1 1 calc R . . C9 C 0.145(8) 0.786(6) 0.753(10) 0.33(6) Uiso 1 1 d DU . . H9A H 0.1886 0.8773 0.7600 0.494 Uiso 1 1 calc . . . H9B H 0.1086 0.7112 0.8285 0.494 Uiso 1 1 calc . . . H9C H 0.0548 0.8070 0.7264 0.494 Uiso 1 1 calc . . . C10 C 0.441(6) 0.817(4) 0.626(5) 0.08(2) Uiso 1 1 d DU . . H10A H 0.4740 0.8702 0.5437 0.114 Uiso 1 1 calc . . . H10B H 0.5209 0.7500 0.6391 0.114 Uiso 1 1 calc . . . H10C H 0.4315 0.8889 0.6703 0.114 Uiso 1 1 calc . . . C11 C 0.691(4) 0.356(4) 0.813(3) 0.068(14) Uiso 1 1 d GU . . C12 C 0.692(4) 0.202(4) 0.863(2) 0.057(13) Uiso 1 1 d GU . . H12 H 0.6168 0.1536 0.9380 0.068 Uiso 1 1 calc R . . C13 C 0.807(4) 0.121(3) 0.802(3) 0.068(15) Uiso 1 1 d GU . . H13 H 0.8078 0.0179 0.8358 0.081 Uiso 1 1 calc R . . C14 C 0.919(4) 0.193(4) 0.691(3) 0.039(13) Uiso 1 1 d GU . . C15 C 0.918(4) 0.347(4) 0.641(2) 0.074(19) Uiso 1 1 d GU . . H15 H 0.9931 0.3953 0.5661 0.088 Uiso 1 1 calc R . . C16 C 0.803(5) 0.428(3) 0.702(3) 0.064(14) Uiso 1 1 d GU . . H16 H 0.8021 0.5311 0.6683 0.076 Uiso 1 1 calc R . . C17 C 1.039(7) 0.114(7) 0.616(5) 0.065(14) Uiso 1 1 d U . . Ru1' Ru -0.3160(5) 0.5686(4) 0.1304(4) 0.0407(17) Uani 1 1 d U . . Cl1' Cl -0.221(3) 0.707(2) -0.0772(17) 0.083(7) Uani 1 1 d U . . Cl2' Cl -0.280(3) 0.337(2) 0.0690(17) 0.086(8) Uani 1 1 d DU . . N1' N -0.045(5) 0.562(5) 0.114(4) 0.058(12) Uiso 1 1 d U . . H1'1 H -0.0273 0.4642 0.1376 0.070 Uiso 1 1 calc R . . H1'2 H 0.0169 0.5975 0.0366 0.070 Uiso 1 1 calc R . . N2' N 0.181(7) 1.027(6) 0.335(5) 0.105(18) Uiso 1 1 d U . . H2'1 H 0.2023 1.0823 0.3740 0.126 Uiso 1 1 calc R . . H2'2 H 0.1694 1.0682 0.2688 0.126 Uiso 1 1 calc R . . O1' O 0.178(4) 0.805(4) 0.472(3) 0.066(10) Uiso 1 1 d U . . C1' C -0.366(10) 0.922(3) 0.127(7) 0.14(3) Uiso 1 1 d DU . . H1'3 H -0.2785 0.9522 0.1482 0.209 Uiso 1 1 calc . . . H1'4 H -0.4593 0.9758 0.1548 0.209 Uiso 1 1 calc . . . H1'5 H -0.3307 0.9459 0.0424 0.209 Uiso 1 1 calc . . . C2' C -0.414(4) 0.753(2) 0.181(2) 0.044(12) Uiso 1 1 d GDU . . C3' C -0.519(4) 0.679(3) 0.147(3) 0.084(16) Uiso 1 1 d GDU . . H3' H -0.5576 0.7319 0.0893 0.101 Uiso 1 1 calc R . . C4' C -0.567(4) 0.525(3) 0.201(3) 0.080(16) Uiso 1 1 d GU . . H4' H -0.6378 0.4753 0.1779 0.096 Uiso 1 1 calc R . . C5' C -0.510(4) 0.445(2) 0.287(3) 0.071(14) Uiso 1 1 d GDU . . C6' C -0.404(4) 0.520(3) 0.321(2) 0.031(13) Uiso 1 1 d GU . . H6' H -0.3660 0.4663 0.3795 0.037 Uiso 1 1 calc R . . C7' C -0.356(4) 0.673(3) 0.268(3) 0.042(12) Uiso 1 1 d GDU . . H7' H -0.2859 0.7229 0.2909 0.050 Uiso 1 1 calc R . . C8' C -0.551(5) 0.277(3) 0.338(4) 0.087(17) Uiso 1 1 d DU . . H8' H -0.6591 0.2622 0.4012 0.105 Uiso 1 1 calc R . . C9' C -0.574(5) 0.202(5) 0.252(4) 0.29(6) Uiso 1 1 d DU . . H9'1 H -0.6883 0.1879 0.2652 0.440 Uiso 1 1 calc . . . H9'2 H -0.5299 0.1057 0.2627 0.440 Uiso 1 1 calc . . . H9'3 H -0.5166 0.2649 0.1732 0.440 Uiso 1 1 calc . . . C10' C -0.437(7) 0.201(5) 0.396(5) 0.08(2) Uiso 1 1 d DU . . H10D H -0.3256 0.2319 0.3437 0.125 Uiso 1 1 calc . . . H10E H -0.4582 0.0933 0.4160 0.125 Uiso 1 1 calc . . . H10F H -0.4539 0.2297 0.4671 0.125 Uiso 1 1 calc . . . C11' C 0.010(4) 0.643(4) 0.177(3) 0.063(13) Uiso 1 1 d GU . . C12' C 0.058(5) 0.798(4) 0.130(2) 0.076(15) Uiso 1 1 d GU . . H12' H 0.0549 0.8492 0.0569 0.091 Uiso 1 1 calc R . . C13' C 0.110(5) 0.875(3) 0.194(3) 0.073(16) Uiso 1 1 d GU . . H13' H 0.1422 0.9786 0.1631 0.088 Uiso 1 1 calc R . . C14' C 0.115(4) 0.798(3) 0.304(3) 0.039(13) Uiso 1 1 d GU . . C15' C 0.067(3) 0.644(3) 0.350(2) 0.012(11) Uiso 1 1 d GU . . H15' H 0.0703 0.5923 0.4236 0.014 Uiso 1 1 calc R . . C16' C 0.015(4) 0.566(3) 0.286(3) 0.048(12) Uiso 1 1 d GU . . H16' H -0.0170 0.4629 0.3174 0.058 Uiso 1 1 calc R . . C17' C 0.164(6) 0.874(6) 0.378(4) 0.046(12) Uiso 1 1 d U . . 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 0.040(4) 0.065(4) 0.024(3) -0.031(3) -0.010(2) 0.003(3) Cl1 0.040(8) 0.031(7) 0.042(6) -0.019(6) 0.013(6) 0.014(6) Cl2 0.15(2) 0.041(8) 0.056(13) -0.029(8) -0.053(13) 0.034(12) Ru1' 0.038(4) 0.033(3) 0.054(4) -0.027(3) -0.009(3) 0.015(3) Cl1' 0.15(2) 0.052(10) 0.061(9) -0.004(9) -0.059(12) 0.002(11) Cl2' 0.13(2) 0.038(9) 0.063(14) -0.037(9) 0.012(12) -0.005(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru1 C4 1.97(4) . ? Ru1 C3 1.96(4) . ? Ru1 C5 2.04(4) . ? Ru1 C2 2.03(4) . ? Ru1 C6 2.10(4) . ? Ru1 C7 2.10(4) . ? Ru1 N1 2.28(6) . ? Ru1 Cl2 2.32(2) . ? Ru1 Cl1 2.45(2) . ? N1 C11 1.41(7) . ? N1 H1A 0.9700 . ? N1 H1B 0.9700 . ? O1 C17 1.36(9) . ? N2 C17 1.38(10) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? C1 C2 1.526(18) . ? C1 H1C 0.9603 . ? C1 H1D 0.9600 . ? C1 H1E 0.9597 . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 C8 1.52(3) . ? C6 C7 1.3900 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C10 1.50(3) . ? C8 C9 1.51(3) . ? C8 H8 0.9800 . ? C9 H9A 0.9590 . ? C9 H9B 0.9607 . ? C9 H9C 0.9606 . ? C10 H10A 0.9595 . ? C10 H10B 0.9592 . ? C10 H10C 0.9612 . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C12 H12 0.9300 . ? C13 C14 1.3900 . ? C13 H13 0.9300 . ? C14 C15 1.3900 . ? C14 C17 1.48(9) . ? C15 C16 1.3900 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? Ru1' C3' 2.01(5) . ? Ru1' C4' 2.05(5) . ? Ru1' C2' 2.06(4) . ? Ru1' C5' 2.14(5) . ? Ru1' C7' 2.14(4) . ? Ru1' C6' 2.18(4) . ? Ru1' N1' 2.30(6) . ? Ru1' Cl1' 2.42(3) . ? Ru1' Cl2' 2.45(3) . ? N1' C11' 1.43(7) . ? N1' H1'1 0.9700 . ? N1' H1'2 0.9700 . ? N2' C17' 1.35(10) . ? N2' H2'1 0.8600 . ? N2' H2'2 0.8600 . ? O1' C17' 1.23(7) . ? C1' C2' 1.523(19) . ? C1' H1'3 0.9605 . ? C1' H1'4 0.9597 . ? C1' H1'5 0.9599 . ? C2' C3' 1.3900 . ? C2' C7' 1.3900 . ? C3' C4' 1.3900 . ? C3' H3' 0.9300 . ? C4' C5' 1.3900 . ? C4' H4' 0.9300 . ? C5' C6' 1.3900 . ? C5' C8' 1.51(3) . ? C6' C7' 1.3900 . ? C6' H6' 0.9300 . ? C7' H7' 0.9300 . ? C8' C9' 1.50(3) . ? C8' C10' 1.50(3) . ? C8' H8' 0.9800 . ? C9' H9'1 0.9590 . ? C9' H9'2 0.9613 . ? C9' H9'3 0.9593 . ? C10' H10D 0.9599 . ? C10' H10E 0.9590 . ? C10' H10F 0.9615 . ? C11' C12' 1.3900 . ? C11' C16' 1.3900 . ? C12' C13' 1.3900 . ? C12' H12' 0.9300 . ? C13' C14' 1.3900 . ? C13' H13' 0.9300 . ? C14' C15' 1.3900 . ? C14' C17' 1.49(8) . ? C15' C16' 1.3900 . ? C15' H15' 0.9300 . ? C16' H16' 0.9300 . ? 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 C4 Ru1 C3 41.4(9) . . ? C4 Ru1 C5 40.6(8) . . ? C3 Ru1 C5 74.0(13) . . ? C4 Ru1 C2 74.1(12) . . ? C3 Ru1 C2 40.7(8) . . ? C5 Ru1 C2 86.3(11) . . ? C4 Ru1 C6 72.5(12) . . ? C3 Ru1 C6 86.3(11) . . ? C5 Ru1 C6 39.2(7) . . ? C2 Ru1 C6 71.3(10) . . ? C4 Ru1 C7 86.3(11) . . ? C3 Ru1 C7 72.7(10) . . ? C5 Ru1 C7 71.2(11) . . ? C2 Ru1 C7 39.4(6) . . ? C6 Ru1 C7 38.7(7) . . ? C4 Ru1 N1 158(2) . . ? C3 Ru1 N1 152.5(19) . . ? C5 Ru1 N1 118(2) . . ? C2 Ru1 N1 112.5(19) . . ? C6 Ru1 N1 89.7(19) . . ? C7 Ru1 N1 87.3(19) . . ? C4 Ru1 Cl2 91.1(14) . . ? C3 Ru1 Cl2 123.4(14) . . ? C5 Ru1 Cl2 86.1(13) . . ? C2 Ru1 Cl2 164.1(14) . . ? C6 Ru1 Cl2 110.3(12) . . ? C7 Ru1 Cl2 147.8(12) . . ? N1 Ru1 Cl2 83.4(17) . . ? C4 Ru1 Cl1 110.4(14) . . ? C3 Ru1 Cl1 85.8(14) . . ? C5 Ru1 Cl1 149.8(14) . . ? C2 Ru1 Cl1 92.9(11) . . ? C6 Ru1 Cl1 162.9(11) . . ? C7 Ru1 Cl1 124.2(11) . . ? N1 Ru1 Cl1 90.2(16) . . ? Cl2 Ru1 Cl1 86.6(8) . . ? C11 N1 Ru1 118(4) . . ? C11 N1 H1A 107.9 . . ? Ru1 N1 H1A 107.9 . . ? C11 N1 H1B 107.9 . . ? Ru1 N1 H1B 107.9 . . ? H1A N1 H1B 107.2 . . ? C17 N2 H2A 120.0 . . ? C17 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 C1 H1C 109.4 . . ? C2 C1 H1D 109.5 . . ? H1C C1 H1D 109.5 . . ? C2 C1 H1E 109.5 . . ? H1C C1 H1E 109.5 . . ? H1D C1 H1E 109.5 . . ? C3 C2 C7 120.0 . . ? C3 C2 C1 120.9(16) . . ? C7 C2 C1 119.0(16) . . ? C3 C2 Ru1 67.1(15) . . ? C7 C2 Ru1 73.0(15) . . ? C1 C2 Ru1 129(5) . . ? C2 C3 C4 120.0 . . ? C2 C3 Ru1 72.2(14) . . ? C4 C3 Ru1 69.5(15) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? Ru1 C3 H3 131.1 . . ? C5 C4 C3 120.0 . . ? C5 C4 Ru1 72.4(15) . . ? C3 C4 Ru1 69.1(15) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? Ru1 C4 H4 131.2 . . ? C4 C5 C6 120.0 . . ? C4 C5 C8 118(3) . . ? C6 C5 C8 122(3) . . ? C4 C5 Ru1 67.0(15) . . ? C6 C5 Ru1 72.8(14) . . ? C8 C5 Ru1 132(4) . . ? C5 C6 C7 120.0 . . ? C5 C6 Ru1 67.9(14) . . ? C7 C6 Ru1 70.5(13) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? Ru1 C6 H6 135.2 . . ? C6 C7 C2 120.0 . . ? C6 C7 Ru1 70.8(14) . . ? C2 C7 Ru1 67.7(15) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? Ru1 C7 H7 135.1 . . ? C10 C8 C9 112(3) . . ? C10 C8 C5 113(3) . . ? C9 C8 C5 112(3) . . ? C10 C8 H8 106.6 . . ? C9 C8 H8 106.7 . . ? C5 C8 H8 106.6 . . ? C8 C9 H9A 109.6 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.4 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.6 . . ? C8 C10 H10C 109.4 . . ? H10A C10 H10C 109.4 . . ? H10B C10 H10C 109.4 . . ? C12 C11 C16 120.0 . . ? C12 C11 N1 126(4) . . ? C16 C11 N1 114(4) . . ? C11 C12 C13 120.0 . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 120.0 . . ? C15 C14 C17 117(5) . . ? C13 C14 C17 123(5) . . ? C14 C15 C16 120.0 . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 120.0 . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? O1 C17 N2 122(8) . . ? O1 C17 C14 121(7) . . ? N2 C17 C14 117(7) . . ? C3' Ru1' C4' 40.0(9) . . ? C3' Ru1' C2' 40.0(8) . . ? C4' Ru1' C2' 71.8(13) . . ? C3' Ru1' C5' 70.9(13) . . ? C4' Ru1' C5' 38.7(8) . . ? C2' Ru1' C5' 83.0(11) . . ? C3' Ru1' C7' 70.8(11) . . ? C4' Ru1' C7' 83.0(11) . . ? C2' Ru1' C7' 38.6(7) . . ? C5' Ru1' C7' 68.4(10) . . ? C3' Ru1' C6' 83.0(11) . . ? C4' Ru1' C6' 69.2(12) . . ? C2' Ru1' C6' 69.2(10) . . ? C5' Ru1' C6' 37.5(7) . . ? C7' Ru1' C6' 37.5(6) . . ? C3' Ru1' N1' 150.8(19) . . ? C4' Ru1' N1' 161(2) . . ? C2' Ru1' N1' 112.0(19) . . ? C5' Ru1' N1' 122.1(19) . . ? C7' Ru1' N1' 89.1(18) . . ? C6' Ru1' N1' 94.0(19) . . ? C3' Ru1' Cl1' 86.7(15) . . ? C4' Ru1' Cl1' 111.6(15) . . ? C2' Ru1' Cl1' 92.9(13) . . ? C5' Ru1' Cl1' 149.7(14) . . ? C7' Ru1' Cl1' 123.9(12) . . ? C6' Ru1' Cl1' 161.1(12) . . ? N1' Ru1' Cl1' 87.3(16) . . ? C3' Ru1' Cl2' 123.4(14) . . ? C4' Ru1' Cl2' 92.5(14) . . ? C2' Ru1' Cl2' 163.2(15) . . ? C5' Ru1' Cl2' 88.4(13) . . ? C7' Ru1' Cl2' 147.9(12) . . ? C6' Ru1' Cl2' 111.5(12) . . ? N1' Ru1' Cl2' 84.8(16) . . ? Cl1' Ru1' Cl2' 87.3(10) . . ? C11' N1' Ru1' 117(4) . . ? C11' N1' H1'1 108.2 . . ? Ru1' N1' H1'1 108.2 . . ? C11' N1' H1'2 108.2 . . ? Ru1' N1' H1'2 108.2 . . ? H1'1 N1' H1'2 107.3 . . ? C17' N2' H2'1 120.0 . . ? C17' N2' H2'2 120.0 . . ? H2'1 N2' H2'2 120.0 . . ? C2' C1' H1'3 109.5 . . ? C2' C1' H1'4 109.5 . . ? H1'3 C1' H1'4 109.5 . . ? C2' C1' H1'5 109.5 . . ? H1'3 C1' H1'5 109.4 . . ? H1'4 C1' H1'5 109.5 . . ? C3' C2' C7' 120.0 . . ? C3' C2' C1' 120.1(16) . . ? C7' C2' C1' 119.8(16) . . ? C3' C2' Ru1' 68.2(17) . . ? C7' C2' Ru1' 74.1(15) . . ? C1' C2' Ru1' 133(6) . . ? C4' C3' C2' 120.0 . . ? C4' C3' Ru1' 71.6(16) . . ? C2' C3' Ru1' 71.8(16) . . ? C4' C3' H3' 120.0 . . ? C2' C3' H3' 120.0 . . ? Ru1' C3' H3' 128.8 . . ? C3' C4' C5' 120.0 . . ? C3' C4' Ru1' 68.3(15) . . ? C5' C4' Ru1' 74.0(15) . . ? C3' C4' H4' 120.0 . . ? C5' C4' H4' 120.0 . . ? Ru1' C4' H4' 130.1 . . ? C4' C5' C6' 120.0 . . ? C4' C5' C8' 119(3) . . ? C6' C5' C8' 120(3) . . ? C4' C5' Ru1' 67.3(15) . . ? C6' C5' Ru1' 73.0(15) . . ? C8' C5' Ru1' 128(3) . . ? C7' C6' C5' 120.0 . . ? C7' C6' Ru1' 69.7(15) . . ? C5' C6' Ru1' 69.5(16) . . ? C7' C6' H6' 120.0 . . ? C5' C6' H6' 120.0 . . ? Ru1' C6' H6' 134.2 . . ? C6' C7' C2' 120.0 . . ? C6' C7' Ru1' 72.8(15) . . ? C2' C7' Ru1' 67.3(15) . . ? C6' C7' H7' 120.0 . . ? C2' C7' H7' 120.0 . . ? Ru1' C7' H7' 132.9 . . ? C9' C8' C10' 113(3) . . ? C9' C8' C5' 113(3) . . ? C10' C8' C5' 113(3) . . ? C9' C8' H8' 105.7 . . ? C10' C8' H8' 105.7 . . ? C5' C8' H8' 105.7 . . ? C8' C9' H9'1 109.5 . . ? C8' C9' H9'2 109.4 . . ? H9'1 C9' H9'2 109.4 . . ? C8' C9' H9'3 109.5 . . ? H9'1 C9' H9'3 109.6 . . ? H9'2 C9' H9'3 109.4 . . ? C8' C10' H10D 109.5 . . ? C8' C10' H10E 109.6 . . ? H10D C10' H10E 109.6 . . ? C8' C10' H10F 109.4 . . ? H10D C10' H10F 109.4 . . ? H10E C10' H10F 109.4 . . ? C12' C11' C16' 120.0 . . ? C12' C11' N1' 121(4) . . ? C16' C11' N1' 119(4) . . ? C11' C12' C13' 120.0 . . ? C11' C12' H12' 120.0 . . ? C13' C12' H12' 120.0 . . ? C14' C13' C12' 120.0 . . ? C14' C13' H13' 120.0 . . ? C12' C13' H13' 120.0 . . ? C13' C14' C15' 120.0 . . ? C13' C14' C17' 123(4) . . ? C15' C14' C17' 117(4) . . ? C16' C15' C14' 120.0 . . ? C16' C15' H15' 120.0 . . ? C14' C15' H15' 120.0 . . ? C15' C16' C11' 120.0 . . ? C15' C16' H16' 120.0 . . ? C11' C16' H16' 120.0 . . ? O1' C17' N2' 125(7) . . ? O1' C17' C14' 122(6) . . ? N2' C17' C14' 112(6) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 18.93 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.171 _refine_diff_density_min -1.314 _refine_diff_density_rms 0.307 _database_code_depnum_ccdc_archive 'CCDC 941877' ####################################################################### # # 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.meOH _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 Cl2 N2 O2 Ru' _chemical_formula_weight 474.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7660(10) _cell_length_b 9.1440(10) _cell_length_c 15.613(2) _cell_angle_alpha 83.304(3) _cell_angle_beta 82.977(3) _cell_angle_gamma 69.036(3) _cell_volume 1024.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 750 _cell_measurement_theta_min 3 _cell_measurement_theta_max 19 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 1.039 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.592031 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 diffractometer _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11534 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 26.45 _reflns_number_total 4192 _reflns_number_gt 3573 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0893P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4192 _refine_ls_number_parameters 250 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.15491(4) 0.19628(3) 0.38761(2) 0.01958(13) Uani 1 1 d . . . . . Cl1 Cl 0.44438(13) 0.20754(12) 0.42154(7) 0.0278(2) Uani 1 1 d . . . . . Cl2 Cl 0.07224(13) 0.17519(11) 0.54250(6) 0.0253(2) Uani 1 1 d . . . . . N1 N 0.2886(5) -0.0564(4) 0.4160(2) 0.0218(7) Uani 1 1 d . . . . . N2 N 0.6344(7) -0.4640(6) 0.0838(3) 0.0459(11) Uani 1 1 d D . . . . O1 O 0.8852(5) -0.4269(4) 0.1210(2) 0.0458(9) Uani 1 1 d . . . . . O2 O 1.2033(5) -0.3686(5) 0.0755(2) 0.0447(9) Uani 1 1 d . . . . . C1 C -0.2698(6) 0.4563(5) 0.4418(3) 0.0339(10) Uani 1 1 d . . . . . H1A H -0.2273 0.5205 0.4722 0.051 Uiso 1 1 calc R U . . . H1B H -0.2967 0.3777 0.4818 0.051 Uiso 1 1 calc R U . . . H1C H -0.3799 0.5207 0.4150 0.051 Uiso 1 1 calc R U . . . C2 C -0.1227(6) 0.3783(5) 0.3737(3) 0.0269(9) Uani 1 1 d . . . . . C3 C 0.0180(6) 0.4416(5) 0.3427(3) 0.0291(9) Uani 1 1 d . . . . . H3 H 0.0176 0.5327 0.3638 0.035 Uiso 1 1 calc R U . . . C4 C 0.1592(6) 0.3654(5) 0.2792(3) 0.0295(9) Uani 1 1 d . . . . . H4 H 0.2487 0.4097 0.2588 0.035 Uiso 1 1 calc R U . . . C5 C 0.1696(6) 0.2264(5) 0.2459(3) 0.0293(9) Uani 1 1 d . . . . . C6 C 0.0289(6) 0.1618(5) 0.2798(3) 0.0268(9) Uani 1 1 d . . . . . H6 H 0.0337 0.0680 0.2602 0.032 Uiso 1 1 calc R U . . . C7 C -0.1152(6) 0.2345(5) 0.3413(3) 0.0276(9) Uani 1 1 d . . . . . H7 H -0.2051 0.1903 0.3609 0.033 Uiso 1 1 calc R U . . . C8 C 0.3144(7) 0.1436(6) 0.1758(3) 0.0376(11) Uani 1 1 d . . . . . H8 H 0.3492 0.0302 0.1906 0.045 Uiso 1 1 calc R U . . . C9 C 0.2268(9) 0.1815(7) 0.0891(3) 0.0565(16) Uani 1 1 d . . . . . H9A H 0.1903 0.2924 0.0733 0.085 Uiso 1 1 calc R U . . . H9B H 0.1201 0.1503 0.0946 0.085 Uiso 1 1 calc R U . . . H9C H 0.3154 0.1255 0.0450 0.085 Uiso 1 1 calc R U . . . C10 C 0.4891(8) 0.1843(7) 0.1690(4) 0.0573(16) Uani 1 1 d . . . . . H10A H 0.4600 0.2939 0.1512 0.086 Uiso 1 1 calc R U . . . H10B H 0.5787 0.1228 0.1271 0.086 Uiso 1 1 calc R U . . . H10C H 0.5389 0.1619 0.2243 0.086 Uiso 1 1 calc R U . . . C11 C 0.3973(5) -0.1507(4) 0.3480(2) 0.0221(8) Uani 1 1 d . . . . . C12 C 0.5765(6) -0.1529(5) 0.3235(3) 0.0270(9) Uani 1 1 d . . . . . H12 H 0.6272 -0.0971 0.3527 0.032 Uiso 1 1 calc R U . . . C13 C 0.6791(6) -0.2389(5) 0.2553(3) 0.0288(9) Uani 1 1 d . . . . . H13 H 0.7995 -0.2415 0.2396 0.035 Uiso 1 1 calc R U . . . C14 C 0.6048(6) -0.3213(5) 0.2099(3) 0.0264(9) Uani 1 1 d . . . . . C15 C 0.4257(6) -0.3208(5) 0.2368(3) 0.0290(9) Uani 1 1 d . . . . . H15 H 0.3753 -0.3779 0.2084 0.035 Uiso 1 1 calc R U . . . C16 C 0.3231(6) -0.2364(5) 0.3049(3) 0.0261(9) Uani 1 1 d . . . . . H16 H 0.2042 -0.2367 0.3220 0.031 Uiso 1 1 calc R U . . . C17 C 0.7199(6) -0.4082(5) 0.1347(3) 0.0323(10) Uani 1 1 d . . . . . C18 C 1.1426(10) -0.2036(7) 0.0638(5) 0.0647(17) Uani 1 1 d . . . . . H18A H 1.0503 -0.1597 0.1096 0.097 Uiso 1 1 calc R U . . . H18B H 1.0905 -0.1693 0.0092 0.097 Uiso 1 1 calc R U . . . H18C H 1.2456 -0.1692 0.0647 0.097 Uiso 1 1 calc R U . . . H1N2 H 0.512(9) -0.441(7) 0.090(4) 0.047(16) Uiso 1 1 d . . . . . H2O H 1.120(8) -0.397(7) 0.088(4) 0.045(17) Uiso 1 1 d . . . . . H2N1 H 0.358(6) -0.071(5) 0.453(3) 0.018(11) Uiso 1 1 d . . . . . H1N1 H 0.212(7) -0.093(6) 0.429(3) 0.032(14) Uiso 1 1 d . . . . . H2N2 H 0.687(9) -0.520(7) 0.035(3) 0.07(2) Uiso 1 1 d 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 0.01894(19) 0.02270(19) 0.01685(19) -0.00215(12) -0.00037(12) -0.00714(13) Cl1 0.0216(5) 0.0338(5) 0.0307(5) -0.0049(4) -0.0022(4) -0.0123(4) Cl2 0.0249(5) 0.0331(5) 0.0181(5) -0.0050(4) 0.0017(4) -0.0106(4) N1 0.0238(18) 0.0259(17) 0.0166(17) -0.0016(13) -0.0027(15) -0.0096(15) N2 0.050(3) 0.055(3) 0.038(3) -0.025(2) 0.016(2) -0.024(2) O1 0.0306(19) 0.060(2) 0.041(2) -0.0156(17) 0.0107(15) -0.0091(16) O2 0.037(2) 0.058(2) 0.044(2) -0.0196(17) 0.0078(16) -0.0216(18) C1 0.024(2) 0.031(2) 0.037(3) -0.0038(18) 0.0034(18) -0.0004(17) C2 0.025(2) 0.029(2) 0.023(2) 0.0013(16) -0.0048(16) -0.0045(16) C3 0.032(2) 0.023(2) 0.032(2) -0.0007(16) -0.0013(18) -0.0094(17) C4 0.034(2) 0.033(2) 0.022(2) 0.0064(17) -0.0014(17) -0.0154(18) C5 0.033(2) 0.027(2) 0.023(2) 0.0017(16) -0.0050(17) -0.0048(17) C6 0.027(2) 0.029(2) 0.024(2) -0.0037(16) -0.0084(17) -0.0076(17) C7 0.021(2) 0.033(2) 0.029(2) -0.0013(17) -0.0064(16) -0.0081(17) C8 0.043(3) 0.039(3) 0.020(2) 0.0016(18) 0.0092(19) -0.006(2) C9 0.081(4) 0.052(3) 0.022(3) -0.002(2) 0.000(3) -0.007(3) C10 0.053(3) 0.061(4) 0.052(4) -0.010(3) 0.029(3) -0.022(3) C11 0.0230(19) 0.0240(19) 0.0175(19) 0.0007(14) -0.0021(15) -0.0064(15) C12 0.023(2) 0.030(2) 0.028(2) -0.0053(17) -0.0039(16) -0.0072(16) C13 0.021(2) 0.033(2) 0.029(2) -0.0013(17) 0.0017(16) -0.0072(17) C14 0.029(2) 0.026(2) 0.021(2) -0.0042(16) 0.0011(16) -0.0066(17) C15 0.032(2) 0.033(2) 0.026(2) -0.0075(17) 0.0022(17) -0.0154(18) C16 0.025(2) 0.030(2) 0.024(2) -0.0046(16) 0.0023(16) -0.0111(17) C17 0.034(2) 0.032(2) 0.029(2) -0.0051(18) 0.0057(19) -0.0101(19) C18 0.074(4) 0.063(4) 0.065(4) -0.001(3) -0.017(3) -0.031(3) _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 C6 2.153(4) . ? Ru1 C4 2.161(4) . ? Ru1 C3 2.183(4) . ? Ru1 N1 2.184(3) . ? Ru1 C5 2.192(4) . ? Ru1 C7 2.199(4) . ? Ru1 C2 2.220(4) . ? Ru1 Cl1 2.4113(10) . ? Ru1 Cl2 2.4284(10) . ? N1 C11 1.434(5) . ? N1 H2N1 0.81(5) . ? N1 H1N1 0.78(5) . ? N2 C17 1.341(7) . ? N2 H1N2 0.89(6) . ? N2 H2N2 0.93(2) . ? O1 C17 1.228(6) . ? O2 C18 1.407(7) . ? O2 H2O 0.78(6) . ? C1 C2 1.497(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.422(6) . ? C2 C7 1.444(6) . ? C3 C4 1.421(6) . ? C3 H3 0.9300 . ? C4 C5 1.400(6) . ? C4 H4 0.9300 . ? C5 C6 1.439(6) . ? C5 C8 1.522(6) . ? C6 C7 1.403(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C10 1.519(8) . ? C8 C9 1.538(7) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.393(6) . ? C11 C12 1.391(6) . ? C12 C13 1.388(6) . ? C12 H12 0.9300 . ? C13 C14 1.392(6) . ? C13 H13 0.9300 . ? C14 C15 1.401(6) . ? C14 C17 1.505(6) . ? C15 C16 1.380(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C6 Ru1 C4 68.06(16) . . ? C6 Ru1 C3 80.98(16) . . ? C4 Ru1 C3 38.19(16) . . ? C6 Ru1 N1 92.09(15) . . ? C4 Ru1 N1 136.40(15) . . ? C3 Ru1 N1 172.63(15) . . ? C6 Ru1 C5 38.67(16) . . ? C4 Ru1 C5 37.52(16) . . ? C3 Ru1 C5 69.01(16) . . ? N1 Ru1 C5 103.97(14) . . ? C6 Ru1 C7 37.59(16) . . ? C4 Ru1 C7 80.67(16) . . ? C3 Ru1 C7 68.47(16) . . ? N1 Ru1 C7 107.39(15) . . ? C5 Ru1 C7 69.21(17) . . ? C6 Ru1 C2 68.38(15) . . ? C4 Ru1 C2 68.29(16) . . ? C3 Ru1 C2 37.66(16) . . ? N1 Ru1 C2 141.24(15) . . ? C5 Ru1 C2 81.81(16) . . ? C7 Ru1 C2 38.14(16) . . ? C6 Ru1 Cl1 140.03(12) . . ? C4 Ru1 Cl1 87.87(12) . . ? C3 Ru1 Cl1 99.82(12) . . ? N1 Ru1 Cl1 83.86(11) . . ? C5 Ru1 Cl1 103.93(12) . . ? C7 Ru1 Cl1 167.77(12) . . ? C2 Ru1 Cl1 132.69(11) . . ? C6 Ru1 Cl2 131.27(12) . . ? C4 Ru1 Cl2 142.34(12) . . ? C3 Ru1 Cl2 106.44(12) . . ? N1 Ru1 Cl2 80.00(9) . . ? C5 Ru1 Cl2 168.38(12) . . ? C7 Ru1 Cl2 99.21(12) . . ? C2 Ru1 Cl2 88.33(11) . . ? Cl1 Ru1 Cl2 87.27(4) . . ? C11 N1 Ru1 119.3(3) . . ? C11 N1 H2N1 105(3) . . ? Ru1 N1 H2N1 109(3) . . ? C11 N1 H1N1 102(4) . . ? Ru1 N1 H1N1 108(4) . . ? H2N1 N1 H1N1 113(5) . . ? C17 N2 H1N2 122(4) . . ? C17 N2 H2N2 127(4) . . ? H1N2 N2 H2N2 111(6) . . ? C18 O2 H2O 111(4) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C7 118.7(4) . . ? C3 C2 C1 120.1(4) . . ? C7 C2 C1 121.1(4) . . ? C3 C2 Ru1 69.8(2) . . ? C7 C2 Ru1 70.1(2) . . ? C1 C2 Ru1 129.8(3) . . ? C4 C3 C2 119.8(4) . . ? C4 C3 Ru1 70.1(2) . . ? C2 C3 Ru1 72.6(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? Ru1 C3 H3 129.7 . . ? C5 C4 C3 122.9(4) . . ? C5 C4 Ru1 72.4(2) . . ? C3 C4 Ru1 71.7(2) . . ? C5 C4 H4 118.6 . . ? C3 C4 H4 118.6 . . ? Ru1 C4 H4 130.1 . . ? C4 C5 C6 116.5(4) . . ? C4 C5 C8 124.7(4) . . ? C6 C5 C8 118.8(4) . . ? C4 C5 Ru1 70.1(2) . . ? C6 C5 Ru1 69.2(2) . . ? C8 C5 Ru1 132.6(3) . . ? C7 C6 C5 122.6(4) . . ? C7 C6 Ru1 72.9(2) . . ? C5 C6 Ru1 72.1(2) . . ? C7 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? Ru1 C6 H6 128.7 . . ? C6 C7 C2 119.4(4) . . ? C6 C7 Ru1 69.5(2) . . ? C2 C7 Ru1 71.7(2) . . ? C6 C7 H7 120.3 . . ? C2 C7 H7 120.3 . . ? Ru1 C7 H7 131.2 . . ? C10 C8 C5 113.1(4) . . ? C10 C8 C9 111.3(5) . . ? C5 C8 C9 108.9(4) . . ? C10 C8 H8 107.8 . . ? C5 C8 H8 107.8 . . ? C9 C8 H8 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 119.9(4) . . ? C16 C11 N1 120.5(4) . . ? C12 C11 N1 119.5(4) . . ? C13 C12 C11 119.6(4) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 121.1(4) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 118.5(4) . . ? C13 C14 C17 118.9(4) . . ? C15 C14 C17 122.6(4) . . ? C16 C15 C14 120.8(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C11 120.1(4) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? O1 C17 N2 121.9(4) . . ? O1 C17 C14 120.9(4) . . ? N2 C17 C14 117.2(4) . . ? O2 C18 H18A 109.5 . . ? O2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.555 _refine_diff_density_min -1.394 _refine_diff_density_rms 0.161 _database_code_depnum_ccdc_archive 'CCDC 941878' ####################################################################### # # 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_2.EtOH _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H32 Cl2 N2 O2 Ru' _chemical_formula_weight 564.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6649(9) _cell_length_b 9.0707(11) _cell_length_c 19.817(2) _cell_angle_alpha 87.882(2) _cell_angle_beta 89.682(2) _cell_angle_gamma 70.084(2) _cell_volume 1294.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 780 _cell_measurement_theta_min 4 _cell_measurement_theta_max 20 _exptl_crystal_description orange _exptl_crystal_colour prism _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.835 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.846493 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 diffractometer _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8648 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.03 _diffrn_reflns_theta_max 23.29 _reflns_number_total 3734 _reflns_number_gt 3259 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The bond lengths and thermal behaviour of the ethanol molecule have been restrained, but the refined geometry is not ideal, due to high anisotropic motions. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+0.5588P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3734 _refine_ls_number_parameters 305 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.938 _refine_ls_shift/su_max 0.002 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.85694(3) 0.81911(3) 0.91163(2) 0.02072(10) Uani 1 1 d . . . . . Cl1 Cl 0.92042(10) 0.81491(9) 1.03154(4) 0.02646(18) Uani 1 1 d . . . . . Cl2 Cl 0.55534(10) 0.81337(9) 0.94241(4) 0.02732(18) Uani 1 1 d . . . . . O1 O 0.2069(4) 1.5117(3) 0.69998(14) 0.0576(8) Uani 1 1 d . . . . . N1 N 0.7310(4) 1.0685(3) 0.93055(14) 0.0226(6) Uani 1 1 d . . . . . N2 N 0.4820(5) 1.5173(4) 0.66118(15) 0.0411(8) Uani 1 1 d . . . . . C5 C 0.8518(4) 0.8053(4) 0.80107(15) 0.0283(7) Uani 1 1 d . . . . . C1 C 1.2772(4) 0.5552(4) 0.95194(17) 0.0337(8) Uani 1 1 d . . . . . H1A H 1.2606 0.4582 0.9654 0.051 Uiso 1 1 calc R U . . . H1B H 1.2631 0.6193 0.9905 0.051 Uiso 1 1 calc R U . . . H1C H 1.3991 0.5340 0.9336 0.051 Uiso 1 1 calc R U . . . C3 C 0.9954(4) 0.5784(4) 0.88079(16) 0.0275(7) Uani 1 1 d . . . . . H3 H 0.9949 0.4832 0.8997 0.033 Uiso 1 1 calc R U . . . C2 C 1.1356(4) 0.6393(4) 0.89979(16) 0.0278(7) Uani 1 1 d . . . . . C14 C 0.4747(5) 1.3698(4) 0.76507(16) 0.0305(8) Uani 1 1 d . . . . . C11 C 0.6424(4) 1.1747(3) 0.87602(15) 0.0248(7) Uani 1 1 d . . . . . C8 C 0.7081(5) 0.8958(4) 0.74948(16) 0.0367(8) Uani 1 1 d . . . . . H8 H 0.6789 1.0077 0.7573 0.044 Uiso 1 1 calc R U . . . C15 C 0.6558(5) 1.3500(4) 0.78383(16) 0.0305(8) Uani 1 1 d . . . . . H15 H 0.7222 1.4017 0.7590 0.037 Uiso 1 1 calc R U . . . C6 C 0.9932(4) 0.8652(4) 0.82210(15) 0.0288(7) Uani 1 1 d . . . . . H6 H 0.9931 0.9608 0.8034 0.035 Uiso 1 1 calc R U . . . C4 C 0.8569(4) 0.6620(4) 0.83339(16) 0.0285(7) Uani 1 1 d . . . . . H4 H 0.7649 0.6210 0.8229 0.034 Uiso 1 1 calc R U . . . C12 C 0.4589(4) 1.1966(4) 0.85930(16) 0.0285(7) Uani 1 1 d . . . . . H12 H 0.3919 1.1465 0.8848 0.034 Uiso 1 1 calc R U . . . C21 C 0.3302(11) 1.8250(7) 0.4915(3) 0.105(2) Uani 1 1 d . . . . . H21 H 0.2990 1.8945 0.4543 0.126 Uiso 1 1 calc R U . . . C7 C 1.1328(4) 0.7848(4) 0.87008(16) 0.0287(7) Uani 1 1 d . . . . . H7 H 1.2223 0.8273 0.8821 0.034 Uiso 1 1 calc R U . . . C16 C 0.7389(4) 1.2538(4) 0.83930(15) 0.0265(7) Uani 1 1 d . . . . . H16 H 0.8597 1.2427 0.8517 0.032 Uiso 1 1 calc R U . . . C17 C 0.3763(5) 1.4720(4) 0.70652(18) 0.0372(8) Uani 1 1 d . . . . . C13 C 0.3769(4) 1.2938(4) 0.80438(16) 0.0312(8) Uani 1 1 d . . . . . H13 H 0.2541 1.3087 0.7934 0.037 Uiso 1 1 calc R U . . . C10 C 0.7918(6) 0.8653(5) 0.67853(19) 0.0617(12) Uani 1 1 d . . . . . H10A H 0.7005 0.9224 0.6454 0.093 Uiso 1 1 calc R U . . . H10B H 0.8298 0.7551 0.6705 0.093 Uiso 1 1 calc R U . . . H10C H 0.8974 0.8992 0.6753 0.093 Uiso 1 1 calc R U . . . C18 C 0.4250(6) 1.6212(5) 0.60370(18) 0.0492(10) Uani 1 1 d . . . . . C9 C 0.5273(5) 0.8613(5) 0.7541(2) 0.0524(11) Uani 1 1 d . . . . . H9A H 0.4426 0.9223 0.7199 0.079 Uiso 1 1 calc R U . . . H9B H 0.4736 0.8880 0.7978 0.079 Uiso 1 1 calc R U . . . H9C H 0.5519 0.7517 0.7476 0.079 Uiso 1 1 calc R U . . . C19 C 0.2418(8) 1.6964(6) 0.5857(2) 0.0864(18) Uani 1 1 d . . . . . H19 H 0.1479 1.6789 0.6111 0.104 Uiso 1 1 calc R U . . . C23 C 0.5568(9) 1.6450(8) 0.5641(3) 0.106(2) Uani 1 1 d . . . . . H23 H 0.6813 1.5914 0.5742 0.127 Uiso 1 1 calc R U . . . C20 C 0.1977(10) 1.7988(7) 0.5292(3) 0.111(2) Uani 1 1 d . . . . . H20 H 0.0738 1.8499 0.5175 0.133 Uiso 1 1 calc R U . . . C22 C 0.5091(12) 1.7495(10) 0.5081(3) 0.138(3) Uani 1 1 d . . . . . H22 H 0.6020 1.7669 0.4821 0.166 Uiso 1 1 calc R U . . . O2 O 0.9130(5) 1.4197(6) 0.6644(2) 0.0823(12) Uani 1 1 d D U . . . C25 C 1.1376(17) 1.1754(10) 0.6387(7) 0.217(6) Uani 1 1 d D U . . . H25A H 1.1157 1.0798 0.6300 0.326 Uiso 1 1 calc R U . . . H25B H 1.1879 1.1690 0.6834 0.326 Uiso 1 1 calc R U . . . H25C H 1.2240 1.1910 0.6064 0.326 Uiso 1 1 calc R U . . . C24 C 0.9882(12) 1.2880(17) 0.6340(8) 0.271(9) Uani 1 1 d D U . . . H24A H 0.8953 1.2377 0.6386 0.325 Uiso 1 1 calc R U . . . H24B H 0.9836 1.3213 0.5867 0.325 Uiso 1 1 calc R U . . . H1N H 0.658(4) 1.070(3) 0.9609(16) 0.013(8) Uiso 1 1 d . . . . . H3N H 0.588(5) 1.494(4) 0.6658(17) 0.025(10) Uiso 1 1 d . . . . . H2N H 0.817(5) 1.093(4) 0.9471(16) 0.025(9) Uiso 1 1 d . . . . . H1O H 0.998(8) 1.447(7) 0.679(3) 0.10(2) 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 Ru1 0.01994(15) 0.01844(15) 0.02431(15) 0.00240(10) -0.00258(10) -0.00749(10) Cl1 0.0273(4) 0.0275(4) 0.0263(4) 0.0048(3) -0.0054(3) -0.0119(3) Cl2 0.0218(4) 0.0293(4) 0.0335(4) 0.0000(3) -0.0005(3) -0.0121(3) O1 0.0406(17) 0.0632(19) 0.0600(18) 0.0225(15) -0.0202(14) -0.0081(14) N1 0.0242(15) 0.0221(15) 0.0227(15) 0.0032(11) -0.0023(13) -0.0100(12) N2 0.047(2) 0.0393(19) 0.0356(18) 0.0094(14) -0.0134(16) -0.0138(17) C5 0.0323(18) 0.0256(18) 0.0233(17) -0.0050(14) 0.0029(14) -0.0047(14) C1 0.0242(17) 0.0270(19) 0.045(2) 0.0020(15) -0.0052(15) -0.0024(14) C3 0.0269(17) 0.0188(16) 0.0343(18) -0.0016(14) 0.0001(14) -0.0044(14) C2 0.0235(17) 0.0217(17) 0.0350(18) -0.0018(14) 0.0029(14) -0.0036(14) C14 0.0368(19) 0.0197(17) 0.0317(18) -0.0006(14) -0.0058(15) -0.0054(15) C11 0.0291(17) 0.0159(16) 0.0273(17) -0.0024(13) -0.0010(14) -0.0047(13) C8 0.041(2) 0.033(2) 0.0278(18) -0.0007(15) -0.0056(16) -0.0023(16) C15 0.0385(19) 0.0275(18) 0.0288(18) 0.0043(14) -0.0037(15) -0.0159(15) C6 0.0316(18) 0.0242(18) 0.0293(18) 0.0013(14) 0.0076(15) -0.0079(15) C4 0.0284(17) 0.0272(18) 0.0317(18) -0.0066(14) -0.0007(14) -0.0113(15) C12 0.0268(17) 0.0262(18) 0.0314(18) -0.0008(14) 0.0031(14) -0.0078(14) C21 0.166(7) 0.101(5) 0.061(4) 0.053(3) -0.046(4) -0.066(5) C7 0.0177(16) 0.0279(18) 0.0384(19) 0.0013(15) 0.0036(14) -0.0055(14) C16 0.0276(17) 0.0242(17) 0.0282(17) 0.0025(14) -0.0059(14) -0.0097(14) C17 0.043(2) 0.030(2) 0.036(2) 0.0029(16) -0.0102(17) -0.0083(17) C13 0.0238(17) 0.0300(19) 0.0370(19) -0.0022(15) -0.0050(15) -0.0054(14) C10 0.069(3) 0.069(3) 0.031(2) 0.003(2) -0.005(2) -0.004(2) C18 0.076(3) 0.044(2) 0.032(2) 0.0080(18) -0.018(2) -0.026(2) C9 0.044(2) 0.061(3) 0.048(2) 0.001(2) -0.0208(19) -0.013(2) C19 0.091(4) 0.076(4) 0.056(3) 0.030(3) -0.002(3) 0.015(3) C23 0.103(4) 0.161(6) 0.076(4) 0.071(4) -0.040(3) -0.080(5) C20 0.134(6) 0.085(4) 0.067(4) 0.038(3) -0.019(4) 0.019(4) C22 0.159(7) 0.205(9) 0.091(5) 0.093(5) -0.050(5) -0.124(7) O2 0.055(2) 0.118(3) 0.081(3) 0.009(2) -0.0005(19) -0.040(2) C25 0.259(14) 0.102(7) 0.277(14) 0.013(8) -0.165(12) -0.044(8) C24 0.088(6) 0.348(18) 0.393(19) -0.277(17) 0.037(9) -0.068(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 Ru1 C4 2.144(3) . ? Ru1 C6 2.153(3) . ? Ru1 N1 2.182(3) . ? Ru1 C3 2.186(3) . ? Ru1 C7 2.190(3) . ? Ru1 C5 2.200(3) . ? Ru1 C2 2.220(3) . ? Ru1 Cl2 2.4048(8) . ? Ru1 Cl1 2.4247(8) . ? O1 C17 1.230(4) . ? N1 C11 1.429(4) . ? N1 H1N 0.82(3) . ? N1 H2N 0.83(4) . ? N2 C17 1.351(5) . ? N2 C18 1.422(5) . ? N2 H3N 0.77(3) . ? C5 C4 1.416(4) . ? C5 C6 1.437(5) . ? C5 C8 1.505(5) . ? C1 C2 1.489(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C3 C4 1.412(4) . ? C3 C2 1.423(4) . ? C3 H3 0.9300 . ? C2 C7 1.418(4) . ? C14 C15 1.388(5) . ? C14 C13 1.397(5) . ? C14 C17 1.493(5) . ? C11 C16 1.382(4) . ? C11 C12 1.392(4) . ? C8 C9 1.523(5) . ? C8 C10 1.537(5) . ? C8 H8 0.9800 . ? C15 C16 1.391(4) . ? C15 H15 0.9300 . ? C6 C7 1.417(4) . ? C6 H6 0.9300 . ? C4 H4 0.9300 . ? C12 C13 1.384(4) . ? C12 H12 0.9300 . ? C21 C22 1.344(9) . ? C21 C20 1.338(9) . ? C21 H21 0.9300 . ? C7 H7 0.9300 . ? C16 H16 0.9300 . ? C13 H13 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C18 C23 1.345(7) . ? C18 C19 1.379(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C19 C20 1.394(7) . ? C19 H19 0.9300 . ? C23 C22 1.398(7) . ? C23 H23 0.9300 . ? C20 H20 0.9300 . ? C22 H22 0.9300 . ? O2 C24 1.306(9) . ? O2 H1O 0.83(6) . ? C25 C24 1.249(10) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? 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 C4 Ru1 C6 68.28(12) . . ? C4 Ru1 N1 138.02(11) . . ? C6 Ru1 N1 92.34(12) . . ? C4 Ru1 C3 38.04(12) . . ? C6 Ru1 C3 80.53(12) . . ? N1 Ru1 C3 172.83(11) . . ? C4 Ru1 C7 80.97(12) . . ? C6 Ru1 C7 38.09(12) . . ? N1 Ru1 C7 106.87(12) . . ? C3 Ru1 C7 67.88(12) . . ? C4 Ru1 C5 38.02(12) . . ? C6 Ru1 C5 38.54(12) . . ? N1 Ru1 C5 104.84(11) . . ? C3 Ru1 C5 69.03(12) . . ? C7 Ru1 C5 69.64(12) . . ? C4 Ru1 C2 68.57(12) . . ? C6 Ru1 C2 68.26(12) . . ? N1 Ru1 C2 139.70(11) . . ? C3 Ru1 C2 37.69(11) . . ? C7 Ru1 C2 37.52(11) . . ? C5 Ru1 C2 82.09(12) . . ? C4 Ru1 Cl2 87.31(9) . . ? C6 Ru1 Cl2 137.66(9) . . ? N1 Ru1 Cl2 83.21(8) . . ? C3 Ru1 Cl2 101.50(8) . . ? C7 Ru1 Cl2 168.12(9) . . ? C5 Ru1 Cl2 102.11(9) . . ? C2 Ru1 Cl2 135.01(8) . . ? C4 Ru1 Cl1 140.18(9) . . ? C6 Ru1 Cl1 133.91(9) . . ? N1 Ru1 Cl1 80.10(7) . . ? C3 Ru1 Cl1 105.39(9) . . ? C7 Ru1 Cl1 100.81(9) . . ? C5 Ru1 Cl1 170.08(9) . . ? C2 Ru1 Cl1 88.61(9) . . ? Cl2 Ru1 Cl1 86.91(3) . . ? C11 N1 Ru1 119.11(19) . . ? C11 N1 H1N 111(2) . . ? Ru1 N1 H1N 103(2) . . ? C11 N1 H2N 111(2) . . ? Ru1 N1 H2N 104(2) . . ? H1N N1 H2N 107(3) . . ? C17 N2 C18 128.8(4) . . ? C17 N2 H3N 122(3) . . ? C18 N2 H3N 109(3) . . ? C4 C5 C6 115.4(3) . . ? C4 C5 C8 124.3(3) . . ? C6 C5 C8 120.3(3) . . ? C4 C5 Ru1 68.85(17) . . ? C6 C5 Ru1 68.94(17) . . ? C8 C5 Ru1 130.9(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 Ru1 69.38(17) . . ? C2 C3 Ru1 72.45(18) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? Ru1 C3 H3 131.1 . . ? C7 C2 C3 118.6(3) . . ? C7 C2 C1 120.8(3) . . ? C3 C2 C1 120.6(3) . . ? C7 C2 Ru1 70.10(17) . . ? C3 C2 Ru1 69.87(17) . . ? C1 C2 Ru1 129.8(2) . . ? C15 C14 C13 118.2(3) . . ? C15 C14 C17 123.7(3) . . ? C13 C14 C17 118.0(3) . . ? C16 C11 C12 120.0(3) . . ? C16 C11 N1 120.3(3) . . ? C12 C11 N1 119.8(3) . . ? C5 C8 C9 113.8(3) . . ? C5 C8 C10 109.2(3) . . ? C9 C8 C10 111.1(3) . . ? C5 C8 H8 107.5 . . ? C9 C8 H8 107.5 . . ? C10 C8 H8 107.5 . . ? C14 C15 C16 120.8(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C7 C6 C5 122.8(3) . . ? C7 C6 Ru1 72.38(17) . . ? C5 C6 Ru1 72.52(17) . . ? C7 C6 H6 118.6 . . ? C5 C6 H6 118.6 . . ? Ru1 C6 H6 129.1 . . ? C5 C4 C3 123.0(3) . . ? C5 C4 Ru1 73.13(18) . . ? C3 C4 Ru1 72.58(18) . . ? C5 C4 H4 118.5 . . ? C3 C4 H4 118.5 . . ? Ru1 C4 H4 128.2 . . ? C11 C12 C13 119.4(3) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C22 C21 C20 119.2(5) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C6 C7 C2 119.8(3) . . ? C6 C7 Ru1 69.54(17) . . ? C2 C7 Ru1 72.38(17) . . ? C6 C7 H7 120.1 . . ? C2 C7 H7 120.1 . . ? Ru1 C7 H7 130.6 . . ? C11 C16 C15 120.1(3) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? O1 C17 N2 121.9(3) . . ? O1 C17 C14 121.2(3) . . ? N2 C17 C14 116.9(3) . . ? C12 C13 C14 121.4(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C23 C18 C19 118.3(4) . . ? C23 C18 N2 118.3(4) . . ? C19 C18 N2 123.4(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C18 C19 C20 119.8(6) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C18 C23 C22 120.8(6) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C21 C20 C19 121.2(6) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C21 C22 C23 120.6(6) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 O2 H1O 108(4) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C25 C24 O2 135.9(12) . . ? C25 C24 H24A 103.2 . . ? O2 C24 H24A 103.2 . . ? C25 C24 H24B 103.2 . . ? O2 C24 H24B 103.2 . . ? H24A C24 H24B 105.2 . . ? _refine_diff_density_max 0.591 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.081 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.997 _database_code_depnum_ccdc_archive 'CCDC 941879' ####################################################################### # # 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_2.H2O _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 Cl2 N2 O2 Ru' _chemical_formula_weight 536.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.516(5) _cell_length_b 9.814(5) _cell_length_c 14.001(5) _cell_angle_alpha 74.216(5) _cell_angle_beta 82.094(5) _cell_angle_gamma 67.846(5) _cell_volume 1164.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 750 _cell_measurement_theta_min 2 _cell_measurement_theta_max 18 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.924 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.35 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type diffractometer _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19231 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 31.83 _reflns_number_total 7426 _reflns_number_gt 6843 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.2917P] 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 7426 _refine_ls_number_parameters 290 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0295 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0684 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.006 _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 1.259477(13) -0.366963(12) 0.371085(8) 0.02468(4) Uani 1 1 d . . . N1 N 1.01399(16) -0.28794(16) 0.35576(11) 0.0313(3) Uani 1 1 d . . . N2 N 0.8044(2) 0.42089(17) 0.12542(12) 0.0399(3) Uani 1 1 d . . . O1 O 0.74926(19) 0.31809(15) 0.01572(10) 0.0509(4) Uani 1 1 d . . . O2 O 0.9689(2) -0.5458(2) 0.29024(13) 0.0634(4) Uani 1 1 d D . . Cl1 Cl 1.22385(5) -0.60230(5) 0.45673(3) 0.03837(9) Uani 1 1 d . . . Cl2 Cl 1.18113(5) -0.28388(5) 0.52346(3) 0.03957(9) Uani 1 1 d . . . C1 C 1.3921(3) -0.5940(3) 0.21462(17) 0.0543(5) Uani 1 1 d . . . H1A H 1.4620 -0.6883 0.2501 0.081 Uiso 1 1 calc R . . H1B H 1.4195 -0.5790 0.1450 0.081 Uiso 1 1 calc R . . H1C H 1.2911 -0.5962 0.2252 0.081 Uiso 1 1 calc R . . C2 C 1.3981(2) -0.4665(2) 0.25153(13) 0.0383(4) Uani 1 1 d . . . C3 C 1.4920(2) -0.4948(2) 0.33105(14) 0.0390(4) Uani 1 1 d . . . H3 H 1.5535 -0.5938 0.3587 0.047 Uiso 1 1 calc R . . C4 C 1.49361(19) -0.3768(2) 0.36843(14) 0.0383(4) Uani 1 1 d . . . H4 H 1.5566 -0.3987 0.4200 0.046 Uiso 1 1 calc R . . C5 C 1.40022(19) -0.2234(2) 0.32867(13) 0.0362(3) Uani 1 1 d . . . C6 C 1.3059(2) -0.19423(19) 0.25044(12) 0.0349(3) Uani 1 1 d . . . H6 H 1.2431 -0.0954 0.2237 0.042 Uiso 1 1 calc R . . C7 C 1.3060(2) -0.3145(2) 0.21221(12) 0.0365(3) Uani 1 1 d . . . H7 H 1.2439 -0.2926 0.1601 0.044 Uiso 1 1 calc R . . C8 C 1.4065(3) -0.1014(2) 0.37320(17) 0.0491(5) Uani 1 1 d . . . H8 H 1.4170 -0.1436 0.4449 0.059 Uiso 1 1 calc R . . C9 C 1.5499(3) -0.0674(3) 0.3318(3) 0.0816(9) Uani 1 1 d . . . H9A H 1.5563 0.0093 0.3595 0.122 Uiso 1 1 calc R . . H9B H 1.5461 -0.0321 0.2608 0.122 Uiso 1 1 calc R . . H9C H 1.6374 -0.1579 0.3489 0.122 Uiso 1 1 calc R . . C10 C 1.2655(3) 0.0430(3) 0.3580(2) 0.0680(7) Uani 1 1 d . . . H10A H 1.1773 0.0181 0.3843 0.102 Uiso 1 1 calc R . . H10B H 1.2551 0.0902 0.2884 0.102 Uiso 1 1 calc R . . H10C H 1.2756 0.1116 0.3919 0.102 Uiso 1 1 calc R . . C11 C 0.94830(17) -0.13824(17) 0.29396(11) 0.0293(3) Uani 1 1 d . . . C12 C 0.91089(19) -0.01186(19) 0.33215(12) 0.0340(3) Uani 1 1 d . . . H12 H 0.9195 -0.0237 0.3995 0.041 Uiso 1 1 calc R . . C13 C 0.8607(2) 0.13194(19) 0.26965(12) 0.0344(3) Uani 1 1 d . . . H13 H 0.8365 0.2163 0.2954 0.041 Uiso 1 1 calc R . . C14 C 0.84609(18) 0.15167(17) 0.16857(12) 0.0305(3) Uani 1 1 d . . . C15 C 0.8771(2) 0.02426(19) 0.13244(12) 0.0352(3) Uani 1 1 d . . . H15 H 0.8633 0.0359 0.0658 0.042 Uiso 1 1 calc R . . C16 C 0.9283(2) -0.11992(19) 0.19440(13) 0.0357(3) Uani 1 1 d . . . H16 H 0.9492 -0.2043 0.1692 0.043 Uiso 1 1 calc R . . C17 C 0.7953(2) 0.30272(18) 0.09656(12) 0.0344(3) Uani 1 1 d . . . C18 C 0.7570(2) 0.57158(19) 0.06533(13) 0.0365(3) Uani 1 1 d . . . C19 C 0.8565(2) 0.6494(2) 0.04275(16) 0.0466(4) Uani 1 1 d . . . H19 H 0.9547 0.6028 0.0655 0.056 Uiso 1 1 calc R . . C20 C 0.8088(3) 0.7977(2) -0.01421(18) 0.0542(5) Uani 1 1 d . . . H20 H 0.8753 0.8505 -0.0296 0.065 Uiso 1 1 calc R . . C21 C 0.6625(3) 0.8671(2) -0.04810(16) 0.0531(5) Uani 1 1 d . . . H21 H 0.6307 0.9666 -0.0859 0.064 Uiso 1 1 calc R . . C22 C 0.5643(3) 0.7888(2) -0.02569(15) 0.0482(5) Uani 1 1 d . . . H22 H 0.4663 0.8353 -0.0489 0.058 Uiso 1 1 calc R . . C23 C 0.6101(2) 0.6416(2) 0.03102(14) 0.0396(4) Uani 1 1 d . . . H23 H 0.5431 0.5893 0.0463 0.048 Uiso 1 1 calc R . . H1N H 0.854(3) 0.408(3) 0.1753(17) 0.044(6) Uiso 1 1 d . . . H1W H 0.890(3) -0.552(4) 0.333(2) 0.124(15) Uiso 1 1 d D . . H2W H 1.059(2) -0.594(4) 0.313(2) 0.110 Uiso 1 1 d D . . H2N H 0.979(2) -0.292(2) 0.4195(17) 0.040(5) Uiso 1 1 d . . . H3N H 0.995(2) -0.356(3) 0.3372(16) 0.042(6) 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 Ru1 0.02841(6) 0.02447(6) 0.02100(6) -0.00282(4) -0.00254(4) -0.01055(4) N1 0.0330(7) 0.0300(6) 0.0297(6) -0.0015(5) -0.0042(5) -0.0127(5) N2 0.0560(9) 0.0300(7) 0.0352(7) -0.0052(6) -0.0144(7) -0.0146(6) O1 0.0799(10) 0.0340(6) 0.0376(7) -0.0050(5) -0.0256(7) -0.0135(7) O2 0.0822(12) 0.0699(11) 0.0496(9) 0.0007(8) -0.0142(9) -0.0461(10) Cl1 0.0445(2) 0.02919(18) 0.0394(2) 0.00054(15) -0.00267(16) -0.01674(16) Cl2 0.0488(2) 0.0462(2) 0.02886(18) -0.01521(16) -0.00024(16) -0.01886(19) C1 0.0686(14) 0.0517(12) 0.0479(11) -0.0261(10) 0.0111(10) -0.0222(11) C2 0.0429(9) 0.0407(9) 0.0311(8) -0.0119(7) 0.0072(7) -0.0154(7) C3 0.0323(8) 0.0373(9) 0.0385(9) -0.0053(7) 0.0030(6) -0.0067(7) C4 0.0312(8) 0.0446(9) 0.0383(9) -0.0028(7) -0.0050(6) -0.0163(7) C5 0.0356(8) 0.0389(8) 0.0364(8) -0.0019(7) -0.0012(6) -0.0209(7) C6 0.0371(8) 0.0331(8) 0.0309(8) 0.0029(6) -0.0011(6) -0.0160(7) C7 0.0419(9) 0.0441(9) 0.0223(7) -0.0037(6) 0.0008(6) -0.0174(7) C8 0.0566(12) 0.0465(10) 0.0559(12) -0.0064(9) -0.0096(9) -0.0328(9) C9 0.0664(16) 0.0709(17) 0.121(3) -0.0020(17) -0.0168(17) -0.0491(14) C10 0.0720(16) 0.0485(12) 0.098(2) -0.0294(13) -0.0048(14) -0.0285(12) C11 0.0275(7) 0.0293(7) 0.0301(7) -0.0034(6) -0.0053(5) -0.0103(6) C12 0.0398(8) 0.0354(8) 0.0254(7) -0.0079(6) -0.0037(6) -0.0106(7) C13 0.0423(9) 0.0313(7) 0.0301(7) -0.0112(6) -0.0039(6) -0.0103(7) C14 0.0344(7) 0.0279(7) 0.0284(7) -0.0059(6) -0.0058(6) -0.0094(6) C15 0.0449(9) 0.0322(8) 0.0290(7) -0.0076(6) -0.0110(6) -0.0109(7) C16 0.0457(9) 0.0287(7) 0.0344(8) -0.0096(6) -0.0119(7) -0.0103(7) C17 0.0407(8) 0.0289(7) 0.0322(8) -0.0065(6) -0.0071(6) -0.0095(6) C18 0.0507(10) 0.0277(7) 0.0322(8) -0.0088(6) -0.0026(7) -0.0138(7) C19 0.0513(11) 0.0404(9) 0.0549(11) -0.0194(9) -0.0008(9) -0.0188(8) C20 0.0711(14) 0.0416(10) 0.0595(13) -0.0188(10) 0.0145(11) -0.0320(10) C21 0.0773(15) 0.0296(8) 0.0451(11) -0.0055(8) 0.0074(10) -0.0167(9) C22 0.0561(12) 0.0346(9) 0.0452(10) -0.0076(8) -0.0051(9) -0.0067(8) C23 0.0466(10) 0.0332(8) 0.0367(9) -0.0069(7) 0.0004(7) -0.0135(7) _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 C7 2.1649(17) . ? Ru1 C6 2.1733(17) . ? Ru1 C3 2.1756(19) . ? Ru1 N1 2.1876(18) . ? Ru1 C4 2.189(2) . ? Ru1 C2 2.1924(17) . ? Ru1 C5 2.2093(18) . ? Ru1 Cl2 2.4130(8) . ? Ru1 Cl1 2.4206(11) . ? N1 C11 1.436(2) . ? N1 H2N 0.90(2) . ? N1 H3N 0.87(2) . ? N2 C17 1.362(2) . ? N2 C18 1.422(2) . ? N2 H1N 0.85(2) . ? O1 C17 1.220(2) . ? O2 H1W 0.904(17) . ? O2 H2W 0.867(17) . ? C1 C2 1.500(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C7 1.413(3) . ? C2 C3 1.426(3) . ? C3 C4 1.400(3) . ? C3 H3 0.9300 . ? C4 C5 1.427(3) . ? C4 H4 0.9300 . ? C5 C6 1.412(2) . ? C5 C8 1.516(3) . ? C6 C7 1.422(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.526(3) . ? C8 C10 1.528(3) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.387(2) . ? C11 C12 1.388(2) . ? C12 C13 1.386(2) . ? C12 H12 0.9300 . ? C13 C14 1.394(2) . ? C13 H13 0.9300 . ? C14 C15 1.390(2) . ? C14 C17 1.493(2) . ? C15 C16 1.386(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C18 C19 1.383(3) . ? C18 C23 1.392(3) . ? C19 C20 1.389(3) . ? C19 H19 0.9300 . ? C20 C21 1.385(4) . ? C20 H20 0.9300 . ? C21 C22 1.376(3) . ? C21 H21 0.9300 . ? C22 C23 1.380(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 C7 Ru1 C6 38.28(7) . . ? C7 Ru1 C3 67.92(7) . . ? C6 Ru1 C3 80.60(7) . . ? C7 Ru1 N1 93.38(6) . . ? C6 Ru1 N1 97.79(6) . . ? C3 Ru1 N1 151.95(7) . . ? C7 Ru1 C4 80.22(7) . . ? C6 Ru1 C4 67.79(7) . . ? C3 Ru1 C4 37.43(7) . . ? N1 Ru1 C4 163.48(6) . . ? C7 Ru1 C2 37.82(7) . . ? C6 Ru1 C2 69.05(8) . . ? C3 Ru1 C2 38.10(7) . . ? N1 Ru1 C2 115.06(7) . . ? C4 Ru1 C2 68.47(7) . . ? C7 Ru1 C5 68.51(7) . . ? C6 Ru1 C5 37.58(6) . . ? C3 Ru1 C5 68.34(8) . . ? N1 Ru1 C5 125.61(7) . . ? C4 Ru1 C5 37.87(7) . . ? C2 Ru1 C5 81.78(7) . . ? C7 Ru1 Cl2 149.51(5) . . ? C6 Ru1 Cl2 112.18(6) . . ? C3 Ru1 Cl2 124.60(5) . . ? N1 Ru1 Cl2 82.17(4) . . ? C4 Ru1 Cl2 95.58(5) . . ? C2 Ru1 Cl2 162.67(5) . . ? C5 Ru1 Cl2 89.58(5) . . ? C7 Ru1 Cl1 121.21(5) . . ? C6 Ru1 Cl1 159.45(5) . . ? C3 Ru1 Cl1 89.53(6) . . ? N1 Ru1 Cl1 82.50(4) . . ? C4 Ru1 Cl1 113.87(5) . . ? C2 Ru1 Cl1 92.10(6) . . ? C5 Ru1 Cl1 151.19(5) . . ? Cl2 Ru1 Cl1 88.27(3) . . ? C11 N1 Ru1 115.18(10) . . ? C11 N1 H2N 111.2(14) . . ? Ru1 N1 H2N 101.9(13) . . ? C11 N1 H3N 113.3(15) . . ? Ru1 N1 H3N 107.5(15) . . ? H2N N1 H3N 107(2) . . ? C17 N2 C18 122.77(15) . . ? C17 N2 H1N 122.5(15) . . ? C18 N2 H1N 113.8(15) . . ? H1W O2 H2W 117(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 C3 117.35(16) . . ? C7 C2 C1 121.45(18) . . ? C3 C2 C1 121.13(18) . . ? C7 C2 Ru1 70.03(10) . . ? C3 C2 Ru1 70.31(10) . . ? C1 C2 Ru1 128.27(14) . . ? C4 C3 C2 121.40(16) . . ? C4 C3 Ru1 71.81(10) . . ? C2 C3 Ru1 71.59(10) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? Ru1 C3 H3 129.9 . . ? C3 C4 C5 121.13(16) . . ? C3 C4 Ru1 70.76(10) . . ? C5 C4 Ru1 71.84(10) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? Ru1 C4 H4 130.7 . . ? C6 C5 C4 117.91(16) . . ? C6 C5 C8 123.69(17) . . ? C4 C5 C8 118.39(16) . . ? C6 C5 Ru1 69.83(10) . . ? C4 C5 Ru1 70.30(10) . . ? C8 C5 Ru1 130.84(13) . . ? C5 C6 C7 120.63(16) . . ? C5 C6 Ru1 72.59(10) . . ? C7 C6 Ru1 70.54(10) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? Ru1 C6 H6 129.7 . . ? C2 C7 C6 121.57(16) . . ? C2 C7 Ru1 72.14(9) . . ? C6 C7 Ru1 71.18(9) . . ? C2 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? Ru1 C7 H7 130.1 . . ? C5 C8 C9 108.2(2) . . ? C5 C8 C10 114.61(18) . . ? C9 C8 C10 111.4(2) . . ? C5 C8 H8 107.4 . . ? C9 C8 H8 107.4 . . ? C10 C8 H8 107.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 119.84(14) . . ? C16 C11 N1 119.64(14) . . ? C12 C11 N1 120.46(14) . . ? C13 C12 C11 119.86(15) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.80(15) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 118.58(15) . . ? C15 C14 C17 117.61(14) . . ? C13 C14 C17 123.79(14) . . ? C16 C15 C14 120.86(15) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C11 119.94(15) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? O1 C17 N2 122.18(16) . . ? O1 C17 C14 121.15(15) . . ? N2 C17 C14 116.67(15) . . ? C19 C18 C23 120.10(17) . . ? C19 C18 N2 119.68(18) . . ? C23 C18 N2 120.21(17) . . ? C18 C19 C20 119.5(2) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 120.3(2) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 119.87(19) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 120.5(2) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C18 119.76(19) . . ? C22 C23 H23 120.1 . . ? C18 C23 H23 120.1 . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 31.83 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.415 _refine_diff_density_min -0.786 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 941880'