# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email kmuniz@iciq.es _publ_contact_author_name 'Kilian Muniz' loop_ _publ_author_name A.Lishchynski J.Streuff M.Nieger 'Kilian Muniz' #============================================================================== data_mun041_m _database_code_depnum_ccdc_archive 'CCDC 772672' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R-Ru)-(p-cymene)-[kappa '2-(N,N)-{(1R,2R)-N-tosyl-1,2-diphenyl- ethylenediamine}]ruthenium methylsulfonamidate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H39 N3 O4 Ru S2' _chemical_formula_sum 'C32 H39 N3 O4 Ru S2' _chemical_formula_weight 694.85 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 212121' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.0303(2) _cell_length_b 13.7496(3) _cell_length_c 25.4242(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3156.75(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3942 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.670 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.85560 _exptl_absorpt_correction_T_max 0.91692 _exptl_absorpt_process_details 'MULABS (Platon, cf. Blessing, 1995)' _exptl_special_details ; dx = 40 mm, 80 sec./deg., 1 deg., 2 sets, 261 frames, mos.= 0.751(2) deg. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17169 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5556 _reflns_number_gt 4792 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0308P)^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 -0.11(3) _refine_ls_number_reflns 5556 _refine_ls_number_parameters 391 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0689 _refine_ls_wR_factor_gt 0.0666 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.976 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.85801(3) 0.70059(2) 0.792007(11) 0.02180(9) Uani 1 1 d . . . C11 C 0.6254(4) 0.7176(3) 0.81200(14) 0.0293(9) Uani 1 1 d . . . H11 H 0.5550 0.7629 0.7990 0.035 Uiso 1 1 calc R . . C12 C 0.7104(4) 0.7424(3) 0.85541(15) 0.0288(10) Uani 1 1 d . . . H12 H 0.6983 0.8045 0.8711 0.035 Uiso 1 1 calc R . . C13 C 0.8165(4) 0.6755(3) 0.87702(14) 0.0291(10) Uani 1 1 d . . . C14 C 0.8349(4) 0.5852(3) 0.85126(13) 0.0262(9) Uani 1 1 d . . . H14 H 0.9048 0.5397 0.8644 0.031 Uiso 1 1 calc R . . C15 C 0.7499(4) 0.5618(3) 0.80591(14) 0.0270(9) Uani 1 1 d . . . H15 H 0.7669 0.5018 0.7884 0.032 Uiso 1 1 calc R . . C16 C 0.6411(4) 0.6256(3) 0.78630(14) 0.0291(9) Uani 1 1 d . . . C17 C 0.5516(4) 0.6014(3) 0.73845(15) 0.0340(10) Uani 1 1 d . . . H17A H 0.6010 0.5496 0.7186 0.051 Uiso 1 1 calc R . . H17B H 0.5424 0.6594 0.7162 0.051 Uiso 1 1 calc R . . H17C H 0.4529 0.5795 0.7492 0.051 Uiso 1 1 calc R . . C18 C 0.9046(4) 0.7059(3) 0.92475(13) 0.0316(9) Uani 1 1 d . . . H18 H 0.9566 0.7679 0.9157 0.038 Uiso 1 1 calc R . . C19 C 0.8021(5) 0.7272(4) 0.97057(16) 0.0503(14) Uani 1 1 d . . . H19A H 0.8607 0.7479 1.0010 0.075 Uiso 1 1 calc R . . H19B H 0.7463 0.6684 0.9795 0.075 Uiso 1 1 calc R . . H19C H 0.7331 0.7791 0.9607 0.075 Uiso 1 1 calc R . . C20 C 1.0233(5) 0.6323(4) 0.94159(19) 0.0514(13) Uani 1 1 d . . . H20A H 1.0771 0.6576 0.9721 0.077 Uiso 1 1 calc R . . H20B H 1.0927 0.6218 0.9125 0.077 Uiso 1 1 calc R . . H20C H 0.9758 0.5706 0.9509 0.077 Uiso 1 1 calc R . . N1 N 1.0175(3) 0.8102(3) 0.81153(12) 0.0277(8) Uani 1 1 d D . . H1 H 0.977(4) 0.8637(18) 0.8150(15) 0.033 Uiso 1 1 d D . . S1 S 1.18478(11) 0.82881(8) 0.80715(4) 0.0318(3) Uani 1 1 d . . . O11 O 1.2492(3) 0.7689(2) 0.76686(11) 0.0398(8) Uani 1 1 d . . . O12 O 1.2169(3) 0.9310(2) 0.80355(14) 0.0544(9) Uani 1 1 d . . . C1 C 1.2701(5) 0.7909(5) 0.86648(17) 0.0760(19) Uani 1 1 d . . . H1A H 1.3750 0.8090 0.8659 0.114 Uiso 1 1 calc R . . H1B H 1.2612 0.7201 0.8700 0.114 Uiso 1 1 calc R . . H1C H 1.2212 0.8225 0.8964 0.114 Uiso 1 1 calc R . . N2 N 0.8285(3) 0.77614(19) 0.71972(10) 0.0195(7) Uani 1 1 d . . . S2 S 0.79264(10) 0.89058(7) 0.72152(4) 0.0252(2) Uani 1 1 d . . . O21 O 0.9194(3) 0.94892(18) 0.70494(11) 0.0292(6) Uani 1 1 d . . . O22 O 0.7272(3) 0.91357(19) 0.77156(10) 0.0289(6) Uani 1 1 d . . . C21 C 0.6540(4) 0.9127(3) 0.67318(13) 0.0239(8) Uani 1 1 d . . . C22 C 0.5141(4) 0.8706(3) 0.67768(15) 0.0277(9) Uani 1 1 d . . . H22 H 0.4880 0.8348 0.7083 0.033 Uiso 1 1 calc R . . C23 C 0.4137(4) 0.8817(3) 0.63681(15) 0.0313(10) Uani 1 1 d . . . H23 H 0.3188 0.8523 0.6395 0.038 Uiso 1 1 calc R . . C24 C 0.4487(4) 0.9348(3) 0.59216(15) 0.0296(10) Uani 1 1 d . . . C25 C 0.5853(4) 0.9811(3) 0.59063(16) 0.0322(10) Uani 1 1 d . . . H25 H 0.6088 1.0216 0.5615 0.039 Uiso 1 1 calc R . . C26 C 0.6869(4) 0.9698(3) 0.63005(14) 0.0293(10) Uani 1 1 d . . . H26 H 0.7804 1.0012 0.6277 0.035 Uiso 1 1 calc R . . C27 C 0.3418(5) 0.9418(3) 0.54615(15) 0.0427(11) Uani 1 1 d . . . H27A H 0.2419 0.9552 0.5593 0.064 Uiso 1 1 calc R . . H27B H 0.3416 0.8801 0.5268 0.064 Uiso 1 1 calc R . . H27C H 0.3730 0.9944 0.5227 0.064 Uiso 1 1 calc R . . C3 C 0.9350(4) 0.7472(3) 0.67801(14) 0.0206(9) Uani 1 1 d . . . H3 H 1.0280 0.7857 0.6828 0.025 Uiso 1 1 calc R . . C31 C 0.8787(4) 0.7643(3) 0.62257(14) 0.0250(9) Uani 1 1 d . . . C32 C 0.7436(4) 0.7242(3) 0.60684(15) 0.0292(10) Uani 1 1 d . . . H32 H 0.6888 0.6848 0.6306 0.035 Uiso 1 1 calc R . . C33 C 0.6893(5) 0.7414(3) 0.55701(16) 0.0384(11) Uani 1 1 d . . . H33 H 0.5971 0.7142 0.5467 0.046 Uiso 1 1 calc R . . C34 C 0.7685(5) 0.7983(4) 0.52193(15) 0.0413(11) Uani 1 1 d . . . H34 H 0.7310 0.8104 0.4876 0.050 Uiso 1 1 calc R . . C35 C 0.9017(5) 0.8368(3) 0.53730(16) 0.0386(11) Uani 1 1 d . . . H35 H 0.9563 0.8758 0.5134 0.046 Uiso 1 1 calc R . . C36 C 0.9575(4) 0.8198(3) 0.58675(14) 0.0279(10) Uani 1 1 d . . . H36 H 1.0507 0.8464 0.5964 0.034 Uiso 1 1 calc R . . C4 C 0.9704(4) 0.6400(3) 0.68775(14) 0.0223(9) Uani 1 1 d . . . H4 H 0.8761 0.6025 0.6839 0.027 Uiso 1 1 calc R . . C41 C 1.0805(5) 0.5978(3) 0.64998(14) 0.0259(10) Uani 1 1 d . . . C42 C 1.2296(4) 0.6214(3) 0.65197(15) 0.0279(10) Uani 1 1 d . . . H42 H 1.2635 0.6663 0.6777 0.033 Uiso 1 1 calc R . . C43 C 1.3297(5) 0.5809(3) 0.61733(15) 0.0367(11) Uani 1 1 d . . . H43 H 1.4316 0.5977 0.6194 0.044 Uiso 1 1 calc R . . C44 C 1.2813(5) 0.5151(3) 0.57926(16) 0.0377(11) Uani 1 1 d . . . H44 H 1.3502 0.4864 0.5557 0.045 Uiso 1 1 calc R . . C45 C 1.1335(5) 0.4919(3) 0.57601(14) 0.0339(10) Uani 1 1 d . . . H45 H 1.0998 0.4482 0.5497 0.041 Uiso 1 1 calc R . . C46 C 1.0340(4) 0.5323(3) 0.61111(15) 0.0293(10) Uani 1 1 d . . . H46 H 0.9322 0.5154 0.6088 0.035 Uiso 1 1 calc R . . N5 N 1.0174(4) 0.6327(2) 0.74331(13) 0.0258(8) Uani 1 1 d D . . H5A H 1.107(3) 0.665(2) 0.7435(14) 0.031 Uiso 1 1 d D . . H5B H 1.040(4) 0.5745(17) 0.7569(14) 0.031 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 0.01994(14) 0.02013(16) 0.02534(15) -0.00050(14) 0.00147(14) 0.00095(15) C11 0.019(2) 0.033(3) 0.036(2) 0.0025(17) 0.0076(17) 0.001(2) C12 0.028(2) 0.029(2) 0.030(2) -0.0016(17) 0.010(2) 0.0059(19) C13 0.029(2) 0.033(3) 0.025(2) -0.0011(17) 0.0121(17) -0.0031(18) C14 0.030(2) 0.025(2) 0.0233(19) 0.0088(16) 0.0051(18) -0.0026(19) C15 0.031(2) 0.020(2) 0.031(2) 0.0009(16) 0.0076(18) -0.0123(18) C16 0.0209(18) 0.032(2) 0.035(2) 0.0077(18) 0.009(2) -0.0083(19) C17 0.029(2) 0.034(3) 0.039(2) 0.006(2) -0.0034(19) -0.011(2) C18 0.036(2) 0.031(2) 0.028(2) -0.007(2) 0.0000(17) -0.002(2) C19 0.065(3) 0.053(4) 0.033(2) -0.013(2) 0.008(2) -0.001(3) C20 0.056(3) 0.044(3) 0.055(3) -0.011(2) -0.020(3) -0.003(3) N1 0.0294(18) 0.022(2) 0.0319(17) -0.0035(16) -0.0096(14) 0.0030(17) S1 0.0275(5) 0.0329(7) 0.0349(6) -0.0024(4) 0.0005(4) -0.0019(4) O11 0.0310(15) 0.044(2) 0.0447(16) -0.0128(14) 0.0079(14) -0.0018(13) O12 0.0404(17) 0.0318(19) 0.091(2) -0.0104(17) 0.0099(18) -0.0118(15) C1 0.040(3) 0.142(6) 0.046(3) 0.008(4) -0.004(2) 0.026(4) N2 0.0199(16) 0.0139(17) 0.0245(16) -0.0011(11) -0.0003(12) 0.0020(12) S2 0.0236(5) 0.0185(6) 0.0335(6) -0.0032(4) -0.0015(4) 0.0021(4) O21 0.0266(13) 0.0201(14) 0.0411(15) -0.0038(13) -0.0061(14) -0.0055(11) O22 0.0301(15) 0.0240(16) 0.0326(15) -0.0077(12) -0.0019(12) 0.0083(13) C21 0.025(2) 0.016(2) 0.031(2) -0.0043(16) 0.0036(19) 0.0069(19) C22 0.026(2) 0.026(2) 0.031(2) 0.0052(18) -0.0022(19) -0.0006(19) C23 0.023(2) 0.029(2) 0.042(2) -0.001(2) 0.0046(19) 0.0023(18) C24 0.029(2) 0.027(3) 0.033(2) -0.0061(18) -0.0003(19) 0.0139(19) C25 0.034(2) 0.026(3) 0.037(2) 0.0085(19) 0.001(2) 0.006(2) C26 0.029(2) 0.024(2) 0.035(2) 0.0032(18) 0.0002(19) -0.0031(18) C27 0.035(3) 0.057(3) 0.036(2) -0.002(2) -0.003(2) 0.012(3) C3 0.0156(19) 0.020(2) 0.026(2) -0.0019(16) -0.0017(17) -0.0019(16) C31 0.023(2) 0.021(2) 0.030(2) -0.0021(16) 0.0036(19) 0.0078(17) C32 0.033(2) 0.025(3) 0.030(2) -0.0012(17) -0.0017(18) 0.0008(19) C33 0.043(3) 0.031(3) 0.042(3) -0.013(2) -0.014(2) 0.004(2) C34 0.057(3) 0.040(3) 0.027(2) -0.004(2) -0.005(2) 0.014(3) C35 0.047(3) 0.041(3) 0.027(2) 0.0059(19) 0.013(2) 0.015(2) C36 0.028(2) 0.025(3) 0.031(2) 0.0000(18) 0.0090(18) 0.0033(19) C4 0.022(2) 0.017(2) 0.028(2) 0.0018(16) 0.0014(17) -0.0003(17) C41 0.038(2) 0.014(2) 0.026(2) 0.0031(17) 0.0014(18) 0.0031(19) C42 0.028(2) 0.028(2) 0.027(2) 0.0002(18) 0.0048(18) 0.0004(19) C43 0.036(3) 0.038(3) 0.035(2) 0.000(2) 0.004(2) 0.005(2) C44 0.047(3) 0.034(3) 0.032(2) 0.008(2) 0.013(2) 0.007(2) C45 0.054(3) 0.025(2) 0.022(2) -0.0013(16) 0.004(2) 0.007(2) C46 0.036(2) 0.021(2) 0.031(2) -0.0003(18) 0.0005(19) -0.0039(19) N5 0.0265(18) 0.020(2) 0.032(2) 0.0011(15) 0.0041(16) 0.0033(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru1 N5 2.116(3) . ? Ru1 N2 2.128(3) . ? Ru1 N1 2.143(3) . ? Ru1 C12 2.169(4) . ? Ru1 C15 2.172(4) . ? Ru1 C11 2.174(4) . ? Ru1 C14 2.197(3) . ? Ru1 C16 2.218(4) . ? Ru1 C13 2.221(3) . ? Ru1 Ar 1.673(2) . ? C11 C12 1.386(5) . ? C11 C16 1.431(5) . ? C11 H11 0.9500 . ? C12 C13 1.437(5) . ? C12 H12 0.9500 . ? C13 C14 1.413(5) . ? C13 C18 1.510(5) . ? C14 C15 1.422(5) . ? C14 H14 0.9500 . ? C15 C16 1.408(5) . ? C15 H15 0.9500 . ? C16 C17 1.498(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.516(5) . ? C18 C20 1.534(6) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N1 S1 1.536(3) . ? N1 H1 0.825(19) . ? S1 O12 1.437(3) . ? S1 O11 1.438(3) . ? S1 C1 1.772(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? N2 C3 1.486(4) . ? N2 S2 1.607(3) . ? S2 O22 1.438(3) . ? S2 O21 1.460(3) . ? S2 C21 1.781(4) . ? C21 C26 1.380(5) . ? C21 C22 1.394(5) . ? C22 C23 1.388(5) . ? C22 H22 0.9500 . ? C23 C24 1.386(5) . ? C23 H23 0.9500 . ? C24 C25 1.389(5) . ? C24 C27 1.519(5) . ? C25 C26 1.368(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C3 C31 1.517(5) . ? C3 C4 1.529(5) . ? C3 H3 1.0000 . ? C31 C36 1.385(5) . ? C31 C32 1.397(5) . ? C32 C33 1.379(5) . ? C32 H32 0.9500 . ? C33 C34 1.385(6) . ? C33 H33 0.9500 . ? C34 C35 1.371(6) . ? C34 H34 0.9500 . ? C35 C36 1.374(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C4 N5 1.478(5) . ? C4 C41 1.499(5) . ? C4 H4 1.0000 . ? C41 C42 1.386(5) . ? C41 C46 1.401(5) . ? C42 C43 1.380(5) . ? C42 H42 0.9500 . ? C43 C44 1.395(6) . ? C43 H43 0.9500 . ? C44 C45 1.375(6) . ? C44 H44 0.9500 . ? C45 C46 1.383(5) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? N5 H5A 0.918(18) . ? N5 H5B 0.894(19) . ? 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 N5 Ru1 N2 78.18(12) . . ? N5 Ru1 N1 89.36(13) . . ? N2 Ru1 N1 86.60(11) . . ? N5 Ru1 C12 165.88(14) . . ? N2 Ru1 C12 115.83(13) . . ? N1 Ru1 C12 93.13(14) . . ? N5 Ru1 C15 90.77(14) . . ? N2 Ru1 C15 120.87(12) . . ? N1 Ru1 C15 151.91(13) . . ? C12 Ru1 C15 80.52(15) . . ? N5 Ru1 C11 147.32(14) . . ? N2 Ru1 C11 91.63(12) . . ? N1 Ru1 C11 121.29(13) . . ? C12 Ru1 C11 37.24(14) . . ? C15 Ru1 C11 67.80(15) . . ? N5 Ru1 C14 98.47(14) . . ? N2 Ru1 C14 158.85(12) . . ? N1 Ru1 C14 114.38(13) . . ? C12 Ru1 C14 67.87(14) . . ? C15 Ru1 C14 37.98(13) . . ? C11 Ru1 C14 79.96(15) . . ? N5 Ru1 C16 110.94(14) . . ? N2 Ru1 C16 93.43(12) . . ? N1 Ru1 C16 159.30(13) . . ? C12 Ru1 C16 68.22(14) . . ? C15 Ru1 C16 37.40(14) . . ? C11 Ru1 C16 38.00(14) . . ? C14 Ru1 C16 68.01(14) . . ? N5 Ru1 C13 128.00(13) . . ? N2 Ru1 C13 153.57(13) . . ? N1 Ru1 C13 89.84(13) . . ? C12 Ru1 C13 38.21(14) . . ? C15 Ru1 C13 68.24(14) . . ? C11 Ru1 C13 68.05(14) . . ? C14 Ru1 C13 37.30(13) . . ? C16 Ru1 C13 80.94(14) . . ? N1 Ru1 Ar 127.7(1) . . ? N2 Ru1 Ar 128.8(1) . . ? N5 Ru1 Ar 129.9(1) . . ? C12 C11 C16 121.7(4) . . ? C12 C11 Ru1 71.2(2) . . ? C16 C11 Ru1 72.7(2) . . ? C12 C11 H11 119.1 . . ? C16 C11 H11 119.1 . . ? Ru1 C11 H11 129.5 . . ? C11 C12 C13 121.1(4) . . ? C11 C12 Ru1 71.6(2) . . ? C13 C12 Ru1 72.8(2) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? Ru1 C12 H12 128.4 . . ? C14 C13 C12 117.6(3) . . ? C14 C13 C18 123.6(4) . . ? C12 C13 C18 118.8(4) . . ? C14 C13 Ru1 70.46(19) . . ? C12 C13 Ru1 69.0(2) . . ? C18 C13 Ru1 130.6(3) . . ? C13 C14 C15 120.7(4) . . ? C13 C14 Ru1 72.2(2) . . ? C15 C14 Ru1 70.0(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? Ru1 C14 H14 130.8 . . ? C16 C15 C14 121.5(4) . . ? C16 C15 Ru1 73.1(2) . . ? C14 C15 Ru1 72.0(2) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? Ru1 C15 H15 127.9 . . ? C15 C16 C11 117.2(4) . . ? C15 C16 C17 121.7(4) . . ? C11 C16 C17 120.9(4) . . ? C15 C16 Ru1 69.5(2) . . ? C11 C16 Ru1 69.3(2) . . ? C17 C16 Ru1 129.2(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 C19 110.4(3) . . ? C13 C18 C20 114.2(3) . . ? C19 C18 C20 109.8(4) . . ? C13 C18 H18 107.4 . . ? C19 C18 H18 107.4 . . ? C20 C18 H18 107.4 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? S1 N1 Ru1 139.6(2) . . ? S1 N1 H1 107(3) . . ? Ru1 N1 H1 111(3) . . ? O12 S1 O11 115.68(18) . . ? O12 S1 N1 111.43(19) . . ? O11 S1 N1 110.74(18) . . ? O12 S1 C1 104.7(3) . . ? O11 S1 C1 105.2(2) . . ? N1 S1 C1 108.5(2) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 N2 S2 114.4(2) . . ? C3 N2 Ru1 113.9(2) . . ? S2 N2 Ru1 118.60(14) . . ? O22 S2 O21 117.19(16) . . ? O22 S2 N2 108.85(15) . . ? O21 S2 N2 111.82(15) . . ? O22 S2 C21 106.50(16) . . ? O21 S2 C21 104.96(17) . . ? N2 S2 C21 106.84(15) . . ? C26 C21 C22 119.8(4) . . ? C26 C21 S2 119.6(3) . . ? C22 C21 S2 120.6(3) . . ? C23 C22 C21 119.0(4) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C24 C23 C22 121.5(4) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? C23 C24 C25 117.8(4) . . ? C23 C24 C27 121.3(4) . . ? C25 C24 C27 120.9(4) . . ? C26 C25 C24 121.6(4) . . ? C26 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? C25 C26 C21 120.1(4) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N2 C3 C31 113.9(3) . . ? N2 C3 C4 106.1(3) . . ? C31 C3 C4 111.7(3) . . ? N2 C3 H3 108.3 . . ? C31 C3 H3 108.3 . . ? C4 C3 H3 108.3 . . ? C36 C31 C32 118.5(4) . . ? C36 C31 C3 121.6(3) . . ? C32 C31 C3 119.8(3) . . ? C33 C32 C31 120.4(4) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C32 C33 C34 120.4(4) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C35 C34 C33 119.2(4) . . ? C35 C34 H34 120.4 . . ? C33 C34 H34 120.4 . . ? C34 C35 C36 121.1(4) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C35 C36 C31 120.4(4) . . ? C35 C36 H36 119.8 . . ? C31 C36 H36 119.8 . . ? N5 C4 C41 113.3(3) . . ? N5 C4 C3 106.3(3) . . ? C41 C4 C3 114.1(3) . . ? N5 C4 H4 107.6 . . ? C41 C4 H4 107.6 . . ? C3 C4 H4 107.6 . . ? C42 C41 C46 117.9(4) . . ? C42 C41 C4 122.0(4) . . ? C46 C41 C4 120.1(4) . . ? C43 C42 C41 121.3(4) . . ? C43 C42 H42 119.4 . . ? C41 C42 H42 119.4 . . ? C42 C43 C44 120.0(4) . . ? C42 C43 H43 120.0 . . ? C44 C43 H43 120.0 . . ? C45 C44 C43 119.7(4) . . ? C45 C44 H44 120.1 . . ? C43 C44 H44 120.1 . . ? C44 C45 C46 120.0(4) . . ? C44 C45 H45 120.0 . . ? C46 C45 H45 120.0 . . ? C45 C46 C41 121.2(4) . . ? C45 C46 H46 119.4 . . ? C41 C46 H46 119.4 . . ? C4 N5 Ru1 109.5(2) . . ? C4 N5 H5A 103(2) . . ? Ru1 N5 H5A 112(2) . . ? C4 N5 H5B 120(3) . . ? Ru1 N5 H5B 109(3) . . ? H5A N5 H5B 103(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 Ru1 C11 C12 156.5(3) . . . . ? N2 Ru1 C11 C12 -133.1(2) . . . . ? N1 Ru1 C11 C12 -46.0(3) . . . . ? C15 Ru1 C11 C12 104.1(3) . . . . ? C14 Ru1 C11 C12 66.5(2) . . . . ? C16 Ru1 C11 C12 133.5(3) . . . . ? C13 Ru1 C11 C12 29.6(2) . . . . ? N5 Ru1 C11 C16 23.1(4) . . . . ? N2 Ru1 C11 C16 93.5(2) . . . . ? N1 Ru1 C11 C16 -179.5(2) . . . . ? C12 Ru1 C11 C16 -133.5(3) . . . . ? C15 Ru1 C11 C16 -29.4(2) . . . . ? C14 Ru1 C11 C16 -67.0(2) . . . . ? C13 Ru1 C11 C16 -103.9(2) . . . . ? C16 C11 C12 C13 -1.1(5) . . . . ? Ru1 C11 C12 C13 -55.6(3) . . . . ? C16 C11 C12 Ru1 54.6(3) . . . . ? N5 Ru1 C12 C11 -118.1(6) . . . . ? N2 Ru1 C12 C11 54.2(3) . . . . ? N1 Ru1 C12 C11 142.0(2) . . . . ? C15 Ru1 C12 C11 -65.6(2) . . . . ? C14 Ru1 C12 C11 -102.9(3) . . . . ? C16 Ru1 C12 C11 -28.8(2) . . . . ? C13 Ru1 C12 C11 -132.3(4) . . . . ? N5 Ru1 C12 C13 14.1(7) . . . . ? N2 Ru1 C12 C13 -173.5(2) . . . . ? N1 Ru1 C12 C13 -85.8(2) . . . . ? C15 Ru1 C12 C13 66.7(2) . . . . ? C11 Ru1 C12 C13 132.3(4) . . . . ? C14 Ru1 C12 C13 29.3(2) . . . . ? C16 Ru1 C12 C13 103.5(2) . . . . ? C11 C12 C13 C14 2.3(5) . . . . ? Ru1 C12 C13 C14 -52.8(3) . . . . ? C11 C12 C13 C18 -179.2(3) . . . . ? Ru1 C12 C13 C18 125.7(3) . . . . ? C11 C12 C13 Ru1 55.1(3) . . . . ? N5 Ru1 C13 C14 -44.2(3) . . . . ? N2 Ru1 C13 C14 144.8(3) . . . . ? N1 Ru1 C13 C14 -133.2(2) . . . . ? C12 Ru1 C13 C14 131.5(3) . . . . ? C15 Ru1 C13 C14 28.8(2) . . . . ? C11 Ru1 C13 C14 102.6(3) . . . . ? C16 Ru1 C13 C14 65.4(2) . . . . ? N5 Ru1 C13 C12 -175.7(2) . . . . ? N2 Ru1 C13 C12 13.2(4) . . . . ? N1 Ru1 C13 C12 95.3(2) . . . . ? C15 Ru1 C13 C12 -102.7(2) . . . . ? C11 Ru1 C13 C12 -28.9(2) . . . . ? C14 Ru1 C13 C12 -131.5(3) . . . . ? C16 Ru1 C13 C12 -66.1(2) . . . . ? N5 Ru1 C13 C18 73.9(4) . . . . ? N2 Ru1 C13 C18 -97.2(4) . . . . ? N1 Ru1 C13 C18 -15.2(4) . . . . ? C12 Ru1 C13 C18 -110.5(5) . . . . ? C15 Ru1 C13 C18 146.8(4) . . . . ? C11 Ru1 C13 C18 -139.3(4) . . . . ? C14 Ru1 C13 C18 118.0(5) . . . . ? C16 Ru1 C13 C18 -176.6(4) . . . . ? C12 C13 C14 C15 -0.6(5) . . . . ? C18 C13 C14 C15 -178.9(3) . . . . ? Ru1 C13 C14 C15 -52.6(3) . . . . ? C12 C13 C14 Ru1 52.0(3) . . . . ? C18 C13 C14 Ru1 -126.3(3) . . . . ? N5 Ru1 C14 C13 146.3(2) . . . . ? N2 Ru1 C14 C13 -134.6(3) . . . . ? N1 Ru1 C14 C13 53.1(3) . . . . ? C12 Ru1 C14 C13 -30.0(2) . . . . ? C15 Ru1 C14 C13 -133.4(3) . . . . ? C11 Ru1 C14 C13 -66.8(2) . . . . ? C16 Ru1 C14 C13 -104.5(2) . . . . ? N5 Ru1 C14 C15 -80.3(2) . . . . ? N2 Ru1 C14 C15 -1.2(5) . . . . ? N1 Ru1 C14 C15 -173.5(2) . . . . ? C12 Ru1 C14 C15 103.4(2) . . . . ? C11 Ru1 C14 C15 66.6(2) . . . . ? C16 Ru1 C14 C15 28.9(2) . . . . ? C13 Ru1 C14 C15 133.4(3) . . . . ? C13 C14 C15 C16 -2.4(5) . . . . ? Ru1 C14 C15 C16 -56.0(3) . . . . ? C13 C14 C15 Ru1 53.6(3) . . . . ? N5 Ru1 C15 C16 -124.8(2) . . . . ? N2 Ru1 C15 C16 -48.1(3) . . . . ? N1 Ru1 C15 C16 145.1(3) . . . . ? C12 Ru1 C15 C16 66.4(2) . . . . ? C11 Ru1 C15 C16 29.8(2) . . . . ? C14 Ru1 C15 C16 132.4(3) . . . . ? C13 Ru1 C15 C16 104.1(2) . . . . ? N5 Ru1 C15 C14 102.8(2) . . . . ? N2 Ru1 C15 C14 179.5(2) . . . . ? N1 Ru1 C15 C14 12.7(4) . . . . ? C12 Ru1 C15 C14 -66.0(2) . . . . ? C11 Ru1 C15 C14 -102.5(2) . . . . ? C16 Ru1 C15 C14 -132.4(3) . . . . ? C13 Ru1 C15 C14 -28.3(2) . . . . ? C14 C15 C16 C11 3.6(5) . . . . ? Ru1 C15 C16 C11 -51.9(3) . . . . ? C14 C15 C16 C17 179.8(3) . . . . ? Ru1 C15 C16 C17 124.3(3) . . . . ? C14 C15 C16 Ru1 55.5(3) . . . . ? C12 C11 C16 C15 -1.8(5) . . . . ? Ru1 C11 C16 C15 52.0(3) . . . . ? C12 C11 C16 C17 -178.1(3) . . . . ? Ru1 C11 C16 C17 -124.2(3) . . . . ? C12 C11 C16 Ru1 -53.9(3) . . . . ? N5 Ru1 C16 C15 61.5(2) . . . . ? N2 Ru1 C16 C15 140.2(2) . . . . ? N1 Ru1 C16 C15 -130.4(4) . . . . ? C12 Ru1 C16 C15 -103.3(2) . . . . ? C11 Ru1 C16 C15 -131.6(3) . . . . ? C14 Ru1 C16 C15 -29.4(2) . . . . ? C13 Ru1 C16 C15 -65.8(2) . . . . ? N5 Ru1 C16 C11 -166.9(2) . . . . ? N2 Ru1 C16 C11 -88.3(2) . . . . ? N1 Ru1 C16 C11 1.2(5) . . . . ? C12 Ru1 C16 C11 28.2(2) . . . . ? C15 Ru1 C16 C11 131.6(3) . . . . ? C14 Ru1 C16 C11 102.2(2) . . . . ? C13 Ru1 C16 C11 65.7(2) . . . . ? N5 Ru1 C16 C17 -53.3(4) . . . . ? N2 Ru1 C16 C17 25.4(4) . . . . ? N1 Ru1 C16 C17 114.8(4) . . . . ? C12 Ru1 C16 C17 141.9(4) . . . . ? C15 Ru1 C16 C17 -114.8(4) . . . . ? C11 Ru1 C16 C17 113.6(4) . . . . ? C14 Ru1 C16 C17 -144.2(4) . . . . ? C13 Ru1 C16 C17 179.4(4) . . . . ? C14 C13 C18 C19 -121.2(4) . . . . ? C12 C13 C18 C19 60.5(5) . . . . ? Ru1 C13 C18 C19 146.5(3) . . . . ? C14 C13 C18 C20 3.1(5) . . . . ? C12 C13 C18 C20 -175.2(3) . . . . ? Ru1 C13 C18 C20 -89.2(5) . . . . ? N5 Ru1 N1 S1 -14.0(3) . . . . ? N2 Ru1 N1 S1 -92.2(3) . . . . ? C12 Ru1 N1 S1 152.1(3) . . . . ? C15 Ru1 N1 S1 76.5(4) . . . . ? C11 Ru1 N1 S1 178.0(3) . . . . ? C14 Ru1 N1 S1 85.1(3) . . . . ? C16 Ru1 N1 S1 177.1(3) . . . . ? C13 Ru1 N1 S1 114.1(3) . . . . ? Ru1 N1 S1 O12 151.4(3) . . . . ? Ru1 N1 S1 O11 21.1(4) . . . . ? Ru1 N1 S1 C1 -93.8(4) . . . . ? N5 Ru1 N2 C3 -3.6(2) . . . . ? N1 Ru1 N2 C3 86.4(2) . . . . ? C12 Ru1 N2 C3 178.2(2) . . . . ? C15 Ru1 N2 C3 -87.4(3) . . . . ? C11 Ru1 N2 C3 -152.3(2) . . . . ? C14 Ru1 N2 C3 -86.5(4) . . . . ? C16 Ru1 N2 C3 -114.3(2) . . . . ? C13 Ru1 N2 C3 169.2(3) . . . . ? N5 Ru1 N2 S2 -142.74(19) . . . . ? N1 Ru1 N2 S2 -52.68(17) . . . . ? C12 Ru1 N2 S2 39.2(2) . . . . ? C15 Ru1 N2 S2 133.53(17) . . . . ? C11 Ru1 N2 S2 68.58(19) . . . . ? C14 Ru1 N2 S2 134.4(3) . . . . ? C16 Ru1 N2 S2 106.58(19) . . . . ? C13 Ru1 N2 S2 30.1(4) . . . . ? C3 N2 S2 O22 -162.7(2) . . . . ? Ru1 N2 S2 O22 -23.8(2) . . . . ? C3 N2 S2 O21 -31.7(3) . . . . ? Ru1 N2 S2 O21 107.25(18) . . . . ? C3 N2 S2 C21 82.7(3) . . . . ? Ru1 N2 S2 C21 -138.45(17) . . . . ? O22 S2 C21 C26 129.1(3) . . . . ? O21 S2 C21 C26 4.2(3) . . . . ? N2 S2 C21 C26 -114.6(3) . . . . ? O22 S2 C21 C22 -52.9(3) . . . . ? O21 S2 C21 C22 -177.8(3) . . . . ? N2 S2 C21 C22 63.3(3) . . . . ? C26 C21 C22 C23 4.2(6) . . . . ? S2 C21 C22 C23 -173.8(3) . . . . ? C21 C22 C23 C24 -0.9(6) . . . . ? C22 C23 C24 C25 -3.3(6) . . . . ? C22 C23 C24 C27 176.3(4) . . . . ? C23 C24 C25 C26 4.4(6) . . . . ? C27 C24 C25 C26 -175.2(4) . . . . ? C24 C25 C26 C21 -1.2(6) . . . . ? C22 C21 C26 C25 -3.1(6) . . . . ? S2 C21 C26 C25 174.9(3) . . . . ? S2 N2 C3 C31 -64.4(4) . . . . ? Ru1 N2 C3 C31 154.8(2) . . . . ? S2 N2 C3 C4 172.3(2) . . . . ? Ru1 N2 C3 C4 31.4(3) . . . . ? N2 C3 C31 C36 124.6(4) . . . . ? C4 C3 C31 C36 -115.2(4) . . . . ? N2 C3 C31 C32 -54.9(5) . . . . ? C4 C3 C31 C32 65.4(4) . . . . ? C36 C31 C32 C33 -1.2(5) . . . . ? C3 C31 C32 C33 178.2(3) . . . . ? C31 C32 C33 C34 0.3(6) . . . . ? C32 C33 C34 C35 0.3(6) . . . . ? C33 C34 C35 C36 0.0(6) . . . . ? C34 C35 C36 C31 -0.9(6) . . . . ? C32 C31 C36 C35 1.5(6) . . . . ? C3 C31 C36 C35 -177.9(4) . . . . ? N2 C3 C4 N5 -52.9(4) . . . . ? C31 C3 C4 N5 -177.6(3) . . . . ? N2 C3 C4 C41 -178.5(3) . . . . ? C31 C3 C4 C41 56.8(4) . . . . ? N5 C4 C41 C42 -49.4(5) . . . . ? C3 C4 C41 C42 72.5(5) . . . . ? N5 C4 C41 C46 130.7(4) . . . . ? C3 C4 C41 C46 -107.5(4) . . . . ? C46 C41 C42 C43 -0.9(6) . . . . ? C4 C41 C42 C43 179.1(3) . . . . ? C41 C42 C43 C44 0.3(6) . . . . ? C42 C43 C44 C45 0.8(6) . . . . ? C43 C44 C45 C46 -1.3(6) . . . . ? C44 C45 C46 C41 0.7(6) . . . . ? C42 C41 C46 C45 0.4(6) . . . . ? C4 C41 C46 C45 -179.6(3) . . . . ? C41 C4 N5 Ru1 177.3(2) . . . . ? C3 C4 N5 Ru1 51.2(3) . . . . ? N2 Ru1 N5 C4 -26.5(2) . . . . ? N1 Ru1 N5 C4 -113.1(3) . . . . ? C12 Ru1 N5 C4 146.5(5) . . . . ? C15 Ru1 N5 C4 95.0(3) . . . . ? C11 Ru1 N5 C4 47.8(4) . . . . ? C14 Ru1 N5 C4 132.3(3) . . . . ? C16 Ru1 N5 C4 62.7(3) . . . . ? C13 Ru1 N5 C4 157.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O22 0.825(19) 2.61(3) 3.150(4) 125(3) . N1 H1 O12 0.825(19) 2.37(4) 2.457(4) 86(3) . N5 H5A O11 0.918(18) 2.02(2) 2.872(4) 155(3) . N5 H5B O21 0.894(19) 2.02(2) 2.905(4) 174(4) 3_746 C14 H14 O21 0.95 2.68 3.237(5) 118.0 3_746 C4 H4 O12 1.00 2.52 3.342(5) 138.8 3_746 C15 H15 O12 0.95 2.54 3.328(5) 140.7 3_746 C17 H17A O12 0.98 2.38 3.318(5) 158.9 3_746 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.913 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.064 #============================================================================== data_mun048_m _database_code_depnum_ccdc_archive 'CCDC 772673' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (S-Ru)-(p-cymene)-[kappa '2-(N,N)-{(1R,2R)-N-tosyl-1,2-diphenyl- ethylenediamine}]ruthenium trifluoromethylsulfonamidate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H36 F3 N3 O4 Ru S2' _chemical_formula_sum 'C32 H36 F3 N3 O4 Ru S2' _chemical_formula_weight 748.83 _chemical_absolute_configuration ad 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 212121' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.0451(1) _cell_length_b 13.9640(1) _cell_length_c 25.3405(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3200.65(6) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4140 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.680 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86345 _exptl_absorpt_correction_T_max 0.99074 _exptl_absorpt_process_details 'MULABS (Platon, cf. Blessing, 1995)' _exptl_special_details ; dx = 40 mm, 90 sec./deg., 1 deg., 5 sets, 571 frames, mos.= 0.543(1) deg. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37931 _diffrn_reflns_av_R_equivalents 0.0903 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5626 _reflns_number_gt 5312 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0358P)^2^+0.6086P] 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 -0.04(2) _refine_ls_number_reflns 5626 _refine_ls_number_parameters 417 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.003 _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 0.63949(3) 0.798363(17) 0.794393(9) 0.01485(7) Uani 1 1 d . . . N1 N 0.4860(3) 0.68657(19) 0.81592(10) 0.0191(6) Uani 1 1 d D . . H1 H 0.534(4) 0.6351(19) 0.8250(13) 0.023 Uiso 1 1 d D . . S1 S 0.32248(9) 0.65908(6) 0.80698(3) 0.01967(18) Uani 1 1 d . . . O11 O 0.2986(3) 0.55880(16) 0.79956(9) 0.0269(5) Uani 1 1 d . . . O12 O 0.2469(3) 0.72495(17) 0.77252(9) 0.0285(6) Uani 1 1 d . . . C1 C 0.2259(4) 0.6782(2) 0.87029(13) 0.0275(8) Uani 1 1 d . . . F11 F 0.3005(2) 0.63639(16) 0.90968(7) 0.0336(5) Uani 1 1 d . . . F12 F 0.2140(3) 0.77113(15) 0.88180(9) 0.0469(6) Uani 1 1 d . . . F13 F 0.0907(2) 0.64074(17) 0.86936(9) 0.0408(6) Uani 1 1 d . . . C11 C 0.8722(4) 0.7832(2) 0.81421(12) 0.0215(7) Uani 1 1 d . . . H11 H 0.9433 0.7389 0.8014 0.026 Uiso 1 1 calc R . . C12 C 0.7882(4) 0.7598(2) 0.85861(13) 0.0241(8) Uani 1 1 d . . . H12 H 0.8027 0.6995 0.8752 0.029 Uiso 1 1 calc R . . C13 C 0.6797(4) 0.8252(2) 0.87991(12) 0.0205(7) Uani 1 1 d . . . C14 C 0.6613(4) 0.9139(2) 0.85309(11) 0.0198(7) Uani 1 1 d . . . H14 H 0.5916 0.9591 0.8661 0.024 Uiso 1 1 calc R . . C15 C 0.7451(4) 0.9364(2) 0.80727(12) 0.0193(7) Uani 1 1 d . . . H15 H 0.7280 0.9953 0.7895 0.023 Uiso 1 1 calc R . . C16 C 0.8530(4) 0.8727(2) 0.78777(11) 0.0203(6) Uani 1 1 d . . . C17 C 0.9450(4) 0.8961(3) 0.73983(13) 0.0248(7) Uani 1 1 d . . . H17A H 0.8954 0.9459 0.7191 0.037 Uiso 1 1 calc R . . H17B H 0.9571 0.8385 0.7182 0.037 Uiso 1 1 calc R . . H17C H 1.0423 0.9193 0.7511 0.037 Uiso 1 1 calc R . . C18 C 0.5939(4) 0.7970(3) 0.92796(12) 0.0261(7) Uani 1 1 d . . . H18 H 0.5383 0.7372 0.9192 0.031 Uiso 1 1 calc R . . C19 C 0.4807(5) 0.8720(3) 0.94538(16) 0.0416(10) Uani 1 1 d . . . H19A H 0.4282 0.8489 0.9767 0.062 Uiso 1 1 calc R . . H19B H 0.4097 0.8830 0.9168 0.062 Uiso 1 1 calc R . . H19C H 0.5316 0.9320 0.9538 0.062 Uiso 1 1 calc R . . C20 C 0.6978(5) 0.7735(3) 0.97336(14) 0.0468(12) Uani 1 1 d . . . H20A H 0.6398 0.7546 1.0043 0.070 Uiso 1 1 calc R . . H20B H 0.7573 0.8300 0.9819 0.070 Uiso 1 1 calc R . . H20C H 0.7630 0.7207 0.9631 0.070 Uiso 1 1 calc R . . N2 N 0.6667(3) 0.72150(16) 0.72201(9) 0.0159(6) Uani 1 1 d . . . S2 S 0.70393(9) 0.60942(5) 0.72440(3) 0.01733(17) Uani 1 1 d . . . O21 O 0.5771(2) 0.55130(14) 0.70895(9) 0.0218(5) Uani 1 1 d . . . O22 O 0.7703(3) 0.58770(16) 0.77459(8) 0.0246(5) Uani 1 1 d . . . C21 C 0.8412(4) 0.5866(2) 0.67546(12) 0.0199(7) Uani 1 1 d . . . C22 C 0.9790(4) 0.6291(2) 0.67904(13) 0.0222(7) Uani 1 1 d . . . H22 H 1.0044 0.6659 0.7092 0.027 Uiso 1 1 calc R . . C23 C 1.0800(4) 0.6177(2) 0.63821(13) 0.0258(7) Uani 1 1 d . . . H23 H 1.1745 0.6471 0.6406 0.031 Uiso 1 1 calc R . . C24 C 1.0440(4) 0.5635(2) 0.59363(13) 0.0258(8) Uani 1 1 d . . . C25 C 0.9106(4) 0.5174(3) 0.59254(13) 0.0288(8) Uani 1 1 d . . . H25 H 0.8881 0.4764 0.5637 0.035 Uiso 1 1 calc R . . C26 C 0.8070(4) 0.5294(2) 0.63277(13) 0.0259(8) Uani 1 1 d . . . H26 H 0.7137 0.4983 0.6308 0.031 Uiso 1 1 calc R . . C27 C 1.1505(5) 0.5567(3) 0.54717(13) 0.0344(9) Uani 1 1 d . . . H27A H 1.1155 0.5078 0.5224 0.052 Uiso 1 1 calc R . . H27B H 1.2491 0.5393 0.5600 0.052 Uiso 1 1 calc R . . H27C H 1.1554 0.6188 0.5292 0.052 Uiso 1 1 calc R . . C3 C 0.5590(4) 0.7491(2) 0.68064(11) 0.0150(6) Uani 1 1 d . . . H3 H 0.4669 0.7105 0.6856 0.018 Uiso 1 1 calc R . . C31 C 0.6154(4) 0.7331(2) 0.62450(12) 0.0185(7) Uani 1 1 d . . . C32 C 0.7489(4) 0.7723(2) 0.60838(13) 0.0245(8) Uani 1 1 d . . . H32 H 0.8043 0.8106 0.6323 0.029 Uiso 1 1 calc R . . C33 C 0.8021(5) 0.7565(3) 0.55815(14) 0.0313(9) Uani 1 1 d . . . H33 H 0.8940 0.7834 0.5476 0.038 Uiso 1 1 calc R . . C34 C 0.7206(4) 0.7008(3) 0.52276(12) 0.0346(9) Uani 1 1 d . . . H34 H 0.7566 0.6900 0.4880 0.042 Uiso 1 1 calc R . . C35 C 0.5891(4) 0.6618(3) 0.53825(13) 0.0303(8) Uani 1 1 d . . . H35 H 0.5340 0.6236 0.5143 0.036 Uiso 1 1 calc R . . C36 C 0.5352(4) 0.6778(2) 0.58912(12) 0.0250(8) Uani 1 1 d . . . H36 H 0.4434 0.6508 0.5995 0.030 Uiso 1 1 calc R . . C4 C 0.5218(4) 0.8545(2) 0.68953(11) 0.0143(6) Uani 1 1 d . . . H4 H 0.6154 0.8916 0.6849 0.017 Uiso 1 1 calc R . . C41 C 0.4105(4) 0.8954(2) 0.65172(11) 0.0179(7) Uani 1 1 d . . . C42 C 0.2614(4) 0.8729(3) 0.65453(13) 0.0239(8) Uani 1 1 d . . . H42 H 0.2281 0.8282 0.6802 0.029 Uiso 1 1 calc R . . C43 C 0.1600(4) 0.9145(3) 0.62048(13) 0.0307(8) Uani 1 1 d . . . H43 H 0.0582 0.8985 0.6231 0.037 Uiso 1 1 calc R . . C44 C 0.2066(5) 0.9792(3) 0.58276(13) 0.0318(9) Uani 1 1 d . . . H44 H 0.1370 1.0082 0.5596 0.038 Uiso 1 1 calc R . . C45 C 0.3547(5) 1.0015(2) 0.57883(12) 0.0285(8) Uani 1 1 d . . . H45 H 0.3869 1.0454 0.5526 0.034 Uiso 1 1 calc R . . C46 C 0.4572(4) 0.9608(2) 0.61272(12) 0.0229(7) Uani 1 1 d . . . H46 H 0.5589 0.9769 0.6097 0.028 Uiso 1 1 calc R . . N5 N 0.4772(3) 0.86364(19) 0.74586(10) 0.0178(6) Uani 1 1 d D . . H5A H 0.386(2) 0.839(2) 0.7501(12) 0.021 Uiso 1 1 d D . . H5B H 0.464(4) 0.9250(15) 0.7576(13) 0.021 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 0.01566(12) 0.01216(11) 0.01673(12) -0.00027(9) -0.00121(10) 0.00073(10) N1 0.0207(15) 0.0140(14) 0.0225(13) 0.0018(11) 0.0012(11) 0.0007(12) S1 0.0193(4) 0.0193(4) 0.0204(4) 0.0006(3) -0.0001(3) -0.0018(3) O11 0.0277(13) 0.0215(12) 0.0313(13) -0.0021(10) 0.0016(11) -0.0059(10) O12 0.0213(13) 0.0318(14) 0.0322(13) 0.0109(10) -0.0063(10) -0.0028(10) C1 0.026(2) 0.0229(19) 0.034(2) 0.0011(14) 0.0044(15) 0.0055(15) F11 0.0293(12) 0.0511(13) 0.0203(10) 0.0008(9) 0.0018(8) 0.0070(10) F12 0.0556(16) 0.0314(13) 0.0536(14) -0.0079(10) 0.0183(12) 0.0124(11) F13 0.0213(12) 0.0538(15) 0.0472(13) 0.0112(10) 0.0081(9) 0.0007(10) C11 0.0128(16) 0.0230(17) 0.0286(16) -0.0021(12) -0.0039(13) 0.0020(15) C12 0.028(2) 0.0213(17) 0.0233(17) 0.0022(13) -0.0139(15) -0.0015(15) C13 0.0221(19) 0.0212(17) 0.0183(16) -0.0049(12) -0.0085(13) 0.0062(13) C14 0.0236(19) 0.0196(16) 0.0161(15) -0.0041(12) -0.0040(13) 0.0003(14) C15 0.0212(17) 0.0127(15) 0.0241(18) -0.0010(12) -0.0051(13) -0.0049(13) C16 0.0183(16) 0.0191(15) 0.0235(16) -0.0053(12) -0.0035(15) -0.0078(14) C17 0.0161(18) 0.0254(18) 0.0329(19) -0.0020(14) 0.0050(14) -0.0045(14) C18 0.035(2) 0.0200(16) 0.0232(16) -0.0020(15) -0.0040(13) -0.0045(17) C19 0.048(3) 0.038(2) 0.038(2) 0.0042(17) 0.0189(19) -0.001(2) C20 0.059(3) 0.061(3) 0.0201(19) 0.0100(17) -0.0098(18) -0.006(2) N2 0.0183(15) 0.0101(13) 0.0194(12) -0.0005(9) 0.0016(10) 0.0018(10) S2 0.0195(4) 0.0110(4) 0.0215(4) 0.0010(3) 0.0022(3) 0.0015(3) O21 0.0248(12) 0.0117(10) 0.0290(12) -0.0007(9) 0.0052(11) -0.0026(9) O22 0.0348(15) 0.0173(12) 0.0215(11) 0.0037(9) 0.0022(10) 0.0053(10) C21 0.0213(19) 0.0126(15) 0.0257(16) 0.0018(12) 0.0025(14) 0.0081(14) C22 0.0203(18) 0.0175(17) 0.0289(18) -0.0016(13) -0.0007(14) 0.0025(14) C23 0.0178(17) 0.0228(18) 0.037(2) 0.0007(14) 0.0011(15) 0.0010(14) C24 0.024(2) 0.0258(19) 0.0278(18) 0.0046(14) 0.0021(14) 0.0095(15) C25 0.031(2) 0.0282(19) 0.0271(18) -0.0082(14) 0.0008(15) 0.0063(16) C26 0.0232(18) 0.0205(18) 0.034(2) -0.0038(14) 0.0017(15) -0.0013(14) C27 0.033(2) 0.038(2) 0.0325(19) 0.0008(15) 0.0065(17) 0.0104(19) C3 0.0150(17) 0.0122(15) 0.0180(16) -0.0023(12) 0.0003(12) -0.0017(13) C31 0.0210(19) 0.0126(15) 0.0218(16) 0.0010(11) -0.0006(13) 0.0050(13) C32 0.032(2) 0.0163(17) 0.0252(18) 0.0003(12) -0.0005(15) -0.0003(14) C33 0.033(2) 0.0286(19) 0.032(2) 0.0076(15) 0.0113(16) 0.0025(17) C34 0.053(3) 0.034(2) 0.0171(16) 0.0033(16) 0.0070(15) 0.016(2) C35 0.039(2) 0.0290(19) 0.0223(18) -0.0076(14) -0.0075(15) 0.0092(17) C36 0.027(2) 0.0247(19) 0.0234(17) -0.0019(13) -0.0053(14) 0.0049(15) C4 0.0158(16) 0.0107(15) 0.0164(16) 0.0005(11) -0.0001(12) 0.0020(12) C41 0.0249(18) 0.0144(16) 0.0145(15) -0.0012(12) -0.0010(12) 0.0012(14) C42 0.0204(18) 0.0273(19) 0.0241(18) 0.0008(14) 0.0005(13) 0.0016(15) C43 0.022(2) 0.043(2) 0.0272(18) 0.0010(15) -0.0024(15) 0.0023(17) C44 0.041(2) 0.031(2) 0.0234(19) -0.0013(14) -0.0122(16) 0.0096(17) C45 0.041(2) 0.0233(17) 0.0210(17) 0.0021(12) -0.0038(17) 0.0028(18) C46 0.029(2) 0.0160(16) 0.0234(17) 0.0005(13) 0.0003(14) -0.0019(15) N5 0.0191(15) 0.0168(14) 0.0175(14) -0.0029(10) -0.0021(11) 0.0031(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 N5 2.121(3) . ? Ru1 N2 2.139(2) . ? Ru1 N1 2.159(3) . ? Ru1 C11 2.175(3) . ? Ru1 C15 2.176(3) . ? Ru1 C12 2.178(3) . ? Ru1 C16 2.199(3) . ? Ru1 C14 2.204(3) . ? Ru1 C13 2.229(3) . ? Ru1 Ar1 1.671(2) . ? N1 S1 1.545(3) . ? N1 H1 0.870(18) . ? S1 O11 1.429(2) . ? S1 O12 1.441(2) . ? S1 C1 1.846(3) . ? C1 F13 1.330(4) . ? C1 F12 1.334(4) . ? C1 F11 1.339(4) . ? C11 C12 1.397(5) . ? C11 C16 1.428(4) . ? C11 H11 0.9500 . ? C12 C13 1.445(5) . ? C12 H12 0.9500 . ? C13 C14 1.423(4) . ? C13 C18 1.496(5) . ? C14 C15 1.421(5) . ? C14 H14 0.9500 . ? C15 C16 1.411(5) . ? C15 H15 0.9500 . ? C16 C17 1.509(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C20 1.521(5) . ? C18 C19 1.529(5) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N2 C3 1.482(4) . ? N2 S2 1.602(2) . ? S2 O22 1.439(2) . ? S2 O21 1.459(2) . ? S2 C21 1.784(3) . ? C21 C26 1.380(5) . ? C21 C22 1.383(5) . ? C22 C23 1.389(5) . ? C22 H22 0.9500 . ? C23 C24 1.399(5) . ? C23 H23 0.9500 . ? C24 C25 1.368(5) . ? C24 C27 1.524(5) . ? C25 C26 1.395(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C3 C4 1.526(4) . ? C3 C31 1.528(4) . ? C3 H3 1.0000 . ? C31 C36 1.387(5) . ? C31 C32 1.388(5) . ? C32 C33 1.379(5) . ? C32 H32 0.9500 . ? C33 C34 1.398(6) . ? C33 H33 0.9500 . ? C34 C35 1.366(5) . ? C34 H34 0.9500 . ? C35 C36 1.396(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C4 N5 1.489(4) . ? C4 C41 1.502(4) . ? C4 H4 1.0000 . ? C41 C42 1.387(5) . ? C41 C46 1.410(4) . ? C42 C43 1.387(5) . ? C42 H42 0.9500 . ? C43 C44 1.381(5) . ? C43 H43 0.9500 . ? C44 C45 1.379(6) . ? C44 H44 0.9500 . ? C45 C46 1.386(5) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? N5 H5A 0.898(18) . ? N5 H5B 0.915(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Ru1 N2 78.34(10) . . ? N5 Ru1 N1 90.71(11) . . ? N2 Ru1 N1 85.86(9) . . ? N5 Ru1 C11 147.75(11) . . ? N2 Ru1 C11 92.16(11) . . ? N1 Ru1 C11 119.59(11) . . ? N5 Ru1 C15 90.57(11) . . ? N2 Ru1 C15 121.51(11) . . ? N1 Ru1 C15 152.23(11) . . ? C11 Ru1 C15 68.09(12) . . ? N5 Ru1 C12 165.14(11) . . ? N2 Ru1 C12 116.46(12) . . ? N1 Ru1 C12 91.70(12) . . ? C11 Ru1 C12 37.43(13) . . ? C15 Ru1 C12 80.55(12) . . ? N5 Ru1 C16 111.15(11) . . ? N2 Ru1 C16 94.03(10) . . ? N1 Ru1 C16 157.70(11) . . ? C11 Ru1 C16 38.12(12) . . ? C15 Ru1 C16 37.62(12) . . ? C12 Ru1 C16 68.36(12) . . ? N5 Ru1 C14 97.97(11) . . ? N2 Ru1 C14 159.37(11) . . ? N1 Ru1 C14 114.61(11) . . ? C11 Ru1 C14 80.14(12) . . ? C15 Ru1 C14 37.87(12) . . ? C12 Ru1 C14 67.75(12) . . ? C16 Ru1 C14 68.12(12) . . ? N5 Ru1 C13 127.19(11) . . ? N2 Ru1 C13 154.04(10) . . ? N1 Ru1 C13 88.90(11) . . ? C11 Ru1 C13 68.53(12) . . ? C15 Ru1 C13 68.51(12) . . ? C12 Ru1 C13 38.25(12) . . ? C16 Ru1 C13 81.47(12) . . ? C14 Ru1 C13 37.44(11) . . ? N1 RU1 Ar1 126.6(1) . . ? N2 Ru1 Ar1 129.7(1) . . ? N5 Ru1 Ar1 129.8(1) . . ? S1 N1 Ru1 139.31(16) . . ? S1 N1 H1 108(3) . . ? Ru1 N1 H1 110(3) . . ? O11 S1 O12 118.29(15) . . ? O11 S1 N1 114.06(15) . . ? O12 S1 N1 112.62(15) . . ? O11 S1 C1 100.63(15) . . ? O12 S1 C1 102.10(16) . . ? N1 S1 C1 106.84(15) . . ? F13 C1 F12 108.2(3) . . ? F13 C1 F11 107.7(3) . . ? F12 C1 F11 107.6(3) . . ? F13 C1 S1 111.3(2) . . ? F12 C1 S1 111.7(2) . . ? F11 C1 S1 110.2(2) . . ? C12 C11 C16 121.1(3) . . ? C12 C11 Ru1 71.4(2) . . ? C16 C11 Ru1 71.86(19) . . ? C12 C11 H11 119.5 . . ? C16 C11 H11 119.5 . . ? Ru1 C11 H11 129.8 . . ? C11 C12 C13 121.6(3) . . ? C11 C12 Ru1 71.14(19) . . ? C13 C12 Ru1 72.77(18) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? Ru1 C12 H12 129.4 . . ? C14 C13 C12 116.8(3) . . ? C14 C13 C18 123.8(3) . . ? C12 C13 C18 119.4(3) . . ? C14 C13 Ru1 70.31(16) . . ? C12 C13 Ru1 68.98(17) . . ? C18 C13 Ru1 131.5(2) . . ? C15 C14 C13 121.3(3) . . ? C15 C14 Ru1 70.01(17) . . ? C13 C14 Ru1 72.25(17) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? Ru1 C14 H14 131.3 . . ? C16 C15 C14 121.0(3) . . ? C16 C15 Ru1 72.08(17) . . ? C14 C15 Ru1 72.12(18) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? Ru1 C15 H15 128.7 . . ? C15 C16 C11 118.2(3) . . ? C15 C16 C17 121.8(3) . . ? C11 C16 C17 120.0(3) . . ? C15 C16 Ru1 70.30(18) . . ? C11 C16 Ru1 70.02(18) . . ? C17 C16 Ru1 130.4(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 C20 110.6(3) . . ? C13 C18 C19 113.7(3) . . ? C20 C18 C19 110.1(3) . . ? C13 C18 H18 107.4 . . ? C20 C18 H18 107.4 . . ? C19 C18 H18 107.4 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C3 N2 S2 114.78(19) . . ? C3 N2 Ru1 113.60(17) . . ? S2 N2 Ru1 118.81(13) . . ? O22 S2 O21 116.61(14) . . ? O22 S2 N2 109.09(13) . . ? O21 S2 N2 111.59(13) . . ? O22 S2 C21 106.65(15) . . ? O21 S2 C21 105.18(14) . . ? N2 S2 C21 107.13(13) . . ? C26 C21 C22 120.1(3) . . ? C26 C21 S2 119.5(3) . . ? C22 C21 S2 120.3(2) . . ? C21 C22 C23 119.6(3) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C24 120.7(3) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 118.4(3) . . ? C25 C24 C27 120.8(3) . . ? C23 C24 C27 120.7(3) . . ? C24 C25 C26 121.5(3) . . ? C24 C25 H25 119.3 . . ? C26 C25 H25 119.3 . . ? C21 C26 C25 119.4(3) . . ? C21 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N2 C3 C4 106.9(2) . . ? N2 C3 C31 113.6(3) . . ? C4 C3 C31 110.6(2) . . ? N2 C3 H3 108.5 . . ? C4 C3 H3 108.5 . . ? C31 C3 H3 108.5 . . ? C36 C31 C32 119.0(3) . . ? C36 C31 C3 120.6(3) . . ? C32 C31 C3 120.4(3) . . ? C33 C32 C31 120.8(3) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C33 C34 119.8(4) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C35 C34 C33 119.8(3) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C34 C35 C36 120.4(3) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 120.2(4) . . ? C31 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? N5 C4 C41 113.4(3) . . ? N5 C4 C3 106.5(2) . . ? C41 C4 C3 114.9(3) . . ? N5 C4 H4 107.2 . . ? C41 C4 H4 107.2 . . ? C3 C4 H4 107.2 . . ? C42 C41 C46 118.3(3) . . ? C42 C41 C4 122.2(3) . . ? C46 C41 C4 119.5(3) . . ? C43 C42 C41 121.1(3) . . ? C43 C42 H42 119.5 . . ? C41 C42 H42 119.5 . . ? C44 C43 C42 120.2(4) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C45 C44 C43 119.6(3) . . ? C45 C44 H44 120.2 . . ? C43 C44 H44 120.2 . . ? C44 C45 C46 120.8(3) . . ? C44 C45 H45 119.6 . . ? C46 C45 H45 119.6 . . ? C45 C46 C41 120.0(3) . . ? C45 C46 H46 120.0 . . ? C41 C46 H46 120.0 . . ? C4 N5 Ru1 109.39(19) . . ? C4 N5 H5A 109(2) . . ? Ru1 N5 H5A 114(2) . . ? C4 N5 H5B 115(2) . . ? Ru1 N5 H5B 108(2) . . ? H5A N5 H5B 101(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 Ru1 N1 S1 -4.2(2) . . . . ? N2 Ru1 N1 S1 -82.4(2) . . . . ? C11 Ru1 N1 S1 -172.6(2) . . . . ? C15 Ru1 N1 S1 88.4(3) . . . . ? C12 Ru1 N1 S1 161.2(2) . . . . ? C16 Ru1 N1 S1 -173.0(2) . . . . ? C14 Ru1 N1 S1 94.9(2) . . . . ? C13 Ru1 N1 S1 123.0(2) . . . . ? Ru1 N1 S1 O11 141.1(2) . . . . ? Ru1 N1 S1 O12 2.7(3) . . . . ? Ru1 N1 S1 C1 -108.7(2) . . . . ? O11 S1 C1 F13 -49.6(3) . . . . ? O12 S1 C1 F13 72.7(2) . . . . ? N1 S1 C1 F13 -168.9(2) . . . . ? O11 S1 C1 F12 -170.6(3) . . . . ? O12 S1 C1 F12 -48.4(3) . . . . ? N1 S1 C1 F12 70.1(3) . . . . ? O11 S1 C1 F11 69.9(3) . . . . ? O12 S1 C1 F11 -167.9(2) . . . . ? N1 S1 C1 F11 -49.4(3) . . . . ? N5 Ru1 C11 C12 155.4(2) . . . . ? N2 Ru1 C11 C12 -133.2(2) . . . . ? N1 Ru1 C11 C12 -46.7(2) . . . . ? C15 Ru1 C11 C12 103.6(2) . . . . ? C16 Ru1 C11 C12 133.0(3) . . . . ? C14 Ru1 C11 C12 66.1(2) . . . . ? C13 Ru1 C11 C12 28.99(19) . . . . ? N5 Ru1 C11 C16 22.4(3) . . . . ? N2 Ru1 C11 C16 93.78(17) . . . . ? N1 Ru1 C11 C16 -179.75(15) . . . . ? C15 Ru1 C11 C16 -29.49(17) . . . . ? C12 Ru1 C11 C16 -133.0(3) . . . . ? C14 Ru1 C11 C16 -66.96(18) . . . . ? C13 Ru1 C11 C16 -104.06(19) . . . . ? C16 C11 C12 C13 -0.6(5) . . . . ? Ru1 C11 C12 C13 -54.8(3) . . . . ? C16 C11 C12 Ru1 54.2(3) . . . . ? N5 Ru1 C12 C11 -120.1(5) . . . . ? N2 Ru1 C12 C11 54.5(2) . . . . ? N1 Ru1 C12 C11 140.71(19) . . . . ? C15 Ru1 C12 C11 -66.1(2) . . . . ? C16 Ru1 C12 C11 -29.03(19) . . . . ? C14 Ru1 C12 C11 -103.3(2) . . . . ? C13 Ru1 C12 C11 -133.2(3) . . . . ? N5 Ru1 C12 C13 13.1(6) . . . . ? N2 Ru1 C12 C13 -172.28(17) . . . . ? N1 Ru1 C12 C13 -86.06(19) . . . . ? C11 Ru1 C12 C13 133.2(3) . . . . ? C15 Ru1 C12 C13 67.1(2) . . . . ? C16 Ru1 C12 C13 104.2(2) . . . . ? C14 Ru1 C12 C13 29.92(19) . . . . ? C11 C12 C13 C14 0.8(5) . . . . ? Ru1 C12 C13 C14 -53.2(2) . . . . ? C11 C12 C13 C18 -179.3(3) . . . . ? Ru1 C12 C13 C18 126.7(3) . . . . ? C11 C12 C13 Ru1 54.0(3) . . . . ? N5 Ru1 C13 C14 -45.2(3) . . . . ? N2 Ru1 C13 C14 146.5(2) . . . . ? N1 Ru1 C13 C14 -135.3(2) . . . . ? C11 Ru1 C13 C14 102.2(2) . . . . ? C15 Ru1 C13 C14 28.2(2) . . . . ? C12 Ru1 C13 C14 130.6(3) . . . . ? C16 Ru1 C13 C14 64.9(2) . . . . ? N5 Ru1 C13 C12 -175.80(19) . . . . ? N2 Ru1 C13 C12 15.9(4) . . . . ? N1 Ru1 C13 C12 94.2(2) . . . . ? C11 Ru1 C13 C12 -28.41(19) . . . . ? C15 Ru1 C13 C12 -102.4(2) . . . . ? C16 Ru1 C13 C12 -65.7(2) . . . . ? C14 Ru1 C13 C12 -130.6(3) . . . . ? N5 Ru1 C13 C18 73.0(3) . . . . ? N2 Ru1 C13 C18 -95.2(4) . . . . ? N1 Ru1 C13 C18 -17.0(3) . . . . ? C11 Ru1 C13 C18 -139.6(3) . . . . ? C15 Ru1 C13 C18 146.4(3) . . . . ? C12 Ru1 C13 C18 -111.2(4) . . . . ? C16 Ru1 C13 C18 -176.8(3) . . . . ? C14 Ru1 C13 C18 118.2(4) . . . . ? C12 C13 C14 C15 0.6(4) . . . . ? C18 C13 C14 C15 -179.4(3) . . . . ? Ru1 C13 C14 C15 -52.0(3) . . . . ? C12 C13 C14 Ru1 52.6(2) . . . . ? C18 C13 C14 Ru1 -127.4(3) . . . . ? N5 Ru1 C14 C15 -80.6(2) . . . . ? N2 Ru1 C14 C15 -2.5(4) . . . . ? N1 Ru1 C14 C15 -175.04(18) . . . . ? C11 Ru1 C14 C15 66.8(2) . . . . ? C12 Ru1 C14 C15 103.7(2) . . . . ? C16 Ru1 C14 C15 29.08(19) . . . . ? C13 Ru1 C14 C15 134.2(3) . . . . ? N5 Ru1 C14 C13 145.2(2) . . . . ? N2 Ru1 C14 C13 -136.8(3) . . . . ? N1 Ru1 C14 C13 50.7(2) . . . . ? C11 Ru1 C14 C13 -67.4(2) . . . . ? C15 Ru1 C14 C13 -134.2(3) . . . . ? C12 Ru1 C14 C13 -30.5(2) . . . . ? C16 Ru1 C14 C13 -105.2(2) . . . . ? C13 C14 C15 C16 -2.1(5) . . . . ? Ru1 C14 C15 C16 -55.1(3) . . . . ? C13 C14 C15 Ru1 53.0(3) . . . . ? N5 Ru1 C15 C16 -125.32(18) . . . . ? N2 Ru1 C15 C16 -48.7(2) . . . . ? N1 Ru1 C15 C16 142.1(2) . . . . ? C11 Ru1 C15 C16 29.86(18) . . . . ? C12 Ru1 C15 C16 66.65(19) . . . . ? C14 Ru1 C15 C16 132.4(3) . . . . ? C13 Ru1 C15 C16 104.5(2) . . . . ? N5 Ru1 C15 C14 102.3(2) . . . . ? N2 Ru1 C15 C14 178.96(17) . . . . ? N1 Ru1 C15 C14 9.7(3) . . . . ? C11 Ru1 C15 C14 -102.5(2) . . . . ? C12 Ru1 C15 C14 -65.7(2) . . . . ? C16 Ru1 C15 C14 -132.4(3) . . . . ? C13 Ru1 C15 C14 -27.91(19) . . . . ? C14 C15 C16 C11 2.3(4) . . . . ? Ru1 C15 C16 C11 -52.9(2) . . . . ? C14 C15 C16 C17 -178.8(3) . . . . ? Ru1 C15 C16 C17 126.0(3) . . . . ? C14 C15 C16 Ru1 55.2(3) . . . . ? C12 C11 C16 C15 -0.9(5) . . . . ? Ru1 C11 C16 C15 53.0(2) . . . . ? C12 C11 C16 C17 -179.9(3) . . . . ? Ru1 C11 C16 C17 -125.9(3) . . . . ? C12 C11 C16 Ru1 -54.0(3) . . . . ? N5 Ru1 C16 C15 61.02(19) . . . . ? N2 Ru1 C16 C15 140.07(18) . . . . ? N1 Ru1 C16 C15 -131.0(3) . . . . ? C11 Ru1 C16 C15 -131.6(3) . . . . ? C12 Ru1 C16 C15 -103.0(2) . . . . ? C14 Ru1 C16 C15 -29.26(18) . . . . ? C13 Ru1 C16 C15 -65.66(18) . . . . ? N5 Ru1 C16 C11 -167.42(17) . . . . ? N2 Ru1 C16 C11 -88.36(17) . . . . ? N1 Ru1 C16 C11 0.6(4) . . . . ? C15 Ru1 C16 C11 131.6(3) . . . . ? C12 Ru1 C16 C11 28.54(18) . . . . ? C14 Ru1 C16 C11 102.30(19) . . . . ? C13 Ru1 C16 C11 65.91(18) . . . . ? N5 Ru1 C16 C17 -54.5(3) . . . . ? N2 Ru1 C16 C17 24.6(3) . . . . ? N1 Ru1 C16 C17 113.5(3) . . . . ? C11 Ru1 C16 C17 112.9(4) . . . . ? C15 Ru1 C16 C17 -115.5(4) . . . . ? C12 Ru1 C16 C17 141.5(3) . . . . ? C14 Ru1 C16 C17 -144.7(3) . . . . ? C13 Ru1 C16 C17 178.9(3) . . . . ? C14 C13 C18 C20 -123.2(4) . . . . ? C12 C13 C18 C20 56.8(4) . . . . ? Ru1 C13 C18 C20 143.9(3) . . . . ? C14 C13 C18 C19 1.3(5) . . . . ? C12 C13 C18 C19 -178.7(3) . . . . ? Ru1 C13 C18 C19 -91.7(4) . . . . ? N5 Ru1 N2 C3 -3.3(2) . . . . ? N1 Ru1 N2 C3 88.3(2) . . . . ? C11 Ru1 N2 C3 -152.2(2) . . . . ? C15 Ru1 N2 C3 -86.7(2) . . . . ? C12 Ru1 N2 C3 178.2(2) . . . . ? C16 Ru1 N2 C3 -114.0(2) . . . . ? C14 Ru1 N2 C3 -84.9(4) . . . . ? C13 Ru1 N2 C3 167.2(2) . . . . ? N5 Ru1 N2 S2 -142.93(18) . . . . ? N1 Ru1 N2 S2 -51.35(16) . . . . ? C11 Ru1 N2 S2 68.17(17) . . . . ? C15 Ru1 N2 S2 133.66(16) . . . . ? C12 Ru1 N2 S2 38.5(2) . . . . ? C16 Ru1 N2 S2 106.30(17) . . . . ? C14 Ru1 N2 S2 135.5(3) . . . . ? C13 Ru1 N2 S2 27.5(3) . . . . ? C3 N2 S2 O22 -162.3(2) . . . . ? Ru1 N2 S2 O22 -23.1(2) . . . . ? C3 N2 S2 O21 -32.0(2) . . . . ? Ru1 N2 S2 O21 107.23(16) . . . . ? C3 N2 S2 C21 82.6(2) . . . . ? Ru1 N2 S2 C21 -138.15(16) . . . . ? O22 S2 C21 C26 128.9(3) . . . . ? O21 S2 C21 C26 4.4(3) . . . . ? N2 S2 C21 C26 -114.4(3) . . . . ? O22 S2 C21 C22 -53.8(3) . . . . ? O21 S2 C21 C22 -178.3(2) . . . . ? N2 S2 C21 C22 62.9(3) . . . . ? C26 C21 C22 C23 3.2(5) . . . . ? S2 C21 C22 C23 -174.1(3) . . . . ? C21 C22 C23 C24 -0.3(5) . . . . ? C22 C23 C24 C25 -3.7(5) . . . . ? C22 C23 C24 C27 175.7(3) . . . . ? C23 C24 C25 C26 4.8(5) . . . . ? C27 C24 C25 C26 -174.6(3) . . . . ? C22 C21 C26 C25 -2.1(5) . . . . ? S2 C21 C26 C25 175.2(3) . . . . ? C24 C25 C26 C21 -2.0(5) . . . . ? S2 N2 C3 C4 172.22(19) . . . . ? Ru1 N2 C3 C4 30.9(3) . . . . ? S2 N2 C3 C31 -65.4(3) . . . . ? Ru1 N2 C3 C31 153.27(19) . . . . ? N2 C3 C31 C36 125.0(3) . . . . ? C4 C3 C31 C36 -114.7(3) . . . . ? N2 C3 C31 C32 -54.0(4) . . . . ? C4 C3 C31 C32 66.3(4) . . . . ? C36 C31 C32 C33 -0.4(5) . . . . ? C3 C31 C32 C33 178.6(3) . . . . ? C31 C32 C33 C34 0.4(5) . . . . ? C32 C33 C34 C35 -0.4(5) . . . . ? C33 C34 C35 C36 0.4(5) . . . . ? C32 C31 C36 C35 0.3(5) . . . . ? C3 C31 C36 C35 -178.6(3) . . . . ? C34 C35 C36 C31 -0.4(5) . . . . ? N2 C3 C4 N5 -52.3(3) . . . . ? C31 C3 C4 N5 -176.5(2) . . . . ? N2 C3 C4 C41 -178.8(3) . . . . ? C31 C3 C4 C41 57.0(4) . . . . ? N5 C4 C41 C42 -49.5(4) . . . . ? C3 C4 C41 C42 73.4(4) . . . . ? N5 C4 C41 C46 128.9(3) . . . . ? C3 C4 C41 C46 -108.3(3) . . . . ? C46 C41 C42 C43 -0.9(5) . . . . ? C4 C41 C42 C43 177.4(3) . . . . ? C41 C42 C43 C44 0.3(5) . . . . ? C42 C43 C44 C45 0.6(5) . . . . ? C43 C44 C45 C46 -0.8(5) . . . . ? C44 C45 C46 C41 0.2(5) . . . . ? C42 C41 C46 C45 0.7(5) . . . . ? C4 C41 C46 C45 -177.7(3) . . . . ? C41 C4 N5 Ru1 177.8(2) . . . . ? C3 C4 N5 Ru1 50.4(3) . . . . ? N2 Ru1 N5 C4 -26.14(19) . . . . ? N1 Ru1 N5 C4 -111.8(2) . . . . ? C11 Ru1 N5 C4 49.1(3) . . . . ? C15 Ru1 N5 C4 96.0(2) . . . . ? C12 Ru1 N5 C4 148.9(4) . . . . ? C16 Ru1 N5 C4 63.7(2) . . . . ? C14 Ru1 N5 C4 133.3(2) . . . . ? C13 Ru1 N5 C4 159.08(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O22 0.870(18) 2.58(3) 3.101(4) 120(3) . N5 H5A O12 0.898(18) 2.11(2) 2.924(4) 150(3) . N5 H5B O21 0.915(18) 1.991(19) 2.902(3) 173(3) 3_656 C15 H15 O11 0.95 2.44 3.226(4) 140.4 3_656 C17 H17A O11 0.98 2.41 3.318(4) 154.7 3_656 C4 H4 O11 1.00 2.49 3.296(4) 137.1 3_656 C46 H46 F11 0.95 2.61 3.337(4) 133.6 3_656 C11 H11 F13 0.95 2.57 3.133(4) 117.9 1_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.858 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.079 #============================================================================== #_eof # End of Crystallographic Information File data_la612f5_0m _database_code_depnum_ccdc_archive 'CCDC 780370' #TrackingRef '1406_web_deposit_cif_file_0_KilianMuniz_1276093335.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H28 N2 O3 S' _chemical_formula_weight 484.59 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.47700(10) _cell_length_b 17.6950(2) _cell_length_c 12.67200(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.7570(2) _cell_angle_gamma 90.00 _cell_volume 2579.94(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9944 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 31.48 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 40781 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 33.45 _reflns_number_total 17828 _reflns_number_gt 15116 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution Sir2007 _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack -0.01(4) _refine_ls_number_reflns 17828 _refine_ls_number_parameters 659 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 C1A C 0.86434(11) 0.24099(9) 0.02941(11) 0.0184(2) Uani 1 1 d . . . H1A H 0.8584 0.1867 0.0060 0.022 Uiso 1 1 calc R . . C3A C 0.76991(12) 0.32172(9) 0.11268(11) 0.0192(3) Uani 1 1 d . . . C4A C 0.69628(12) 0.38068(9) 0.12033(12) 0.0208(3) Uani 1 1 d . . . C5A C 0.59216(13) 0.40327(10) 0.02915(14) 0.0254(3) Uani 1 1 d . . . H5A H 0.5673 0.3775 -0.0421 0.030 Uiso 1 1 calc R . . C6A C 0.52733(14) 0.46206(12) 0.04349(16) 0.0313(3) Uani 1 1 d . . . H6A H 0.4584 0.4770 -0.0184 0.038 Uiso 1 1 calc R . . C7A C 0.56199(16) 0.50081(12) 0.14954(17) 0.0365(4) Uani 1 1 d . . . H7A H 0.5154 0.5406 0.1590 0.044 Uiso 1 1 calc R . . C8A C 0.66252(17) 0.48072(12) 0.23801(16) 0.0344(4) Uani 1 1 d . . . H8A H 0.6850 0.5068 0.3089 0.041 Uiso 1 1 calc R . . C9A C 0.73423(14) 0.42134(10) 0.22588(13) 0.0265(3) Uani 1 1 d . . . C10A C 0.84397(15) 0.40436(11) 0.31383(13) 0.0288(3) Uani 1 1 d . . . H10A H 0.8674 0.4303 0.3848 0.035 Uiso 1 1 calc R . . C11A C 0.91639(13) 0.35141(11) 0.29828(12) 0.0260(3) Uani 1 1 d . . . H11A H 0.9913 0.3431 0.3560 0.031 Uiso 1 1 calc R . . C12A C 0.87909(12) 0.30944(9) 0.19615(12) 0.0203(3) Uani 1 1 d . . . C13A C 0.94174(12) 0.24936(10) 0.15790(12) 0.0218(3) Uani 1 1 d . . . C14A C 0.70483(12) 0.14324(10) 0.11962(12) 0.0210(3) Uani 1 1 d . . . C15A C 0.74813(13) 0.07246(10) 0.10839(14) 0.0256(3) Uani 1 1 d . . . H14A H 0.7418 0.0548 0.0354 0.031 Uiso 1 1 calc R . . C16A C 0.80103(16) 0.02770(11) 0.20565(16) 0.0325(4) Uani 1 1 d . . . H15A H 0.8305 -0.0207 0.1983 0.039 Uiso 1 1 calc R . . C17A C 0.81115(15) 0.05299(12) 0.31290(15) 0.0319(4) Uani 1 1 d . . . C18A C 0.76526(15) 0.12353(12) 0.32171(14) 0.0311(4) Uani 1 1 d . . . H17A H 0.7707 0.1409 0.3945 0.037 Uiso 1 1 calc R . . C19A C 0.71189(14) 0.16882(10) 0.22632(13) 0.0260(3) Uani 1 1 d . . . H18A H 0.6806 0.2166 0.2335 0.031 Uiso 1 1 calc R . . C20A C 0.8736(2) 0.00565(16) 0.41811(19) 0.0475(5) Uani 1 1 d . . . H19D H 0.9576 0.0130 0.4431 0.071 Uiso 1 1 calc R . . H19E H 0.8547 -0.0478 0.4000 0.071 Uiso 1 1 calc R . . H19F H 0.8488 0.0210 0.4795 0.071 Uiso 1 1 calc R . . C21A C 0.90709(12) 0.28880(9) -0.04684(12) 0.0199(3) Uani 1 1 d . . . H20A H 0.8426 0.2964 -0.1220 0.024 Uiso 1 1 calc R . . H20B H 0.9315 0.3390 -0.0113 0.024 Uiso 1 1 calc R . . C22A C 1.00865(11) 0.25130(9) -0.06446(11) 0.0171(2) Uani 1 1 d . . . C23A C 1.19053(12) 0.26749(9) -0.08949(13) 0.0205(3) Uani 1 1 d . . . H22A H 1.2193 0.2193 -0.0467 0.025 Uiso 1 1 calc R . . C24A C 1.14843(13) 0.25085(10) -0.21667(13) 0.0236(3) Uani 1 1 d . . . C25A C 1.19014(15) 0.18845(11) -0.25561(15) 0.0313(4) Uani 1 1 d . . . H24A H 1.2452 0.1559 -0.2021 0.038 Uiso 1 1 calc R . . C26A C 1.15228(19) 0.17320(13) -0.37173(17) 0.0408(5) Uani 1 1 d . . . H25A H 1.1824 0.1309 -0.3974 0.049 Uiso 1 1 calc R . . C27A C 1.07076(19) 0.21956(15) -0.45024(16) 0.0446(5) Uani 1 1 d . . . H26A H 1.0437 0.2087 -0.5297 0.053 Uiso 1 1 calc R . . C28A C 1.02889(19) 0.28184(15) -0.41236(16) 0.0447(5) Uani 1 1 d . . . H27A H 0.9733 0.3140 -0.4661 0.054 Uiso 1 1 calc R . . C29A C 1.06764(16) 0.29767(13) -0.29607(15) 0.0346(4) Uani 1 1 d . . . H28A H 1.0387 0.3407 -0.2708 0.041 Uiso 1 1 calc R . . C30A C 1.28951(13) 0.32510(11) -0.04946(16) 0.0293(3) Uani 1 1 d . . . H29A H 1.2640 0.3720 -0.0932 0.044 Uiso 1 1 calc R . . H29B H 1.3568 0.3047 -0.0616 0.044 Uiso 1 1 calc R . . H29C H 1.3111 0.3356 0.0321 0.044 Uiso 1 1 calc R . . C1B C 0.12720(13) 0.00708(10) 0.16298(12) 0.0248(3) Uani 1 1 d . . . H1B H 0.1062 -0.0445 0.1809 0.030 Uiso 1 1 calc R . . C3B C 0.26513(12) 0.10211(10) 0.24246(12) 0.0238(3) Uani 1 1 d . . . C4B C 0.30467(13) 0.17367(11) 0.29040(13) 0.0259(3) Uani 1 1 d . . . C5B C 0.27096(14) 0.20988(12) 0.37262(13) 0.0298(3) Uani 1 1 d . . . H5B H 0.2218 0.1842 0.4023 0.036 Uiso 1 1 calc R . . C6B C 0.30859(18) 0.28171(13) 0.40976(15) 0.0388(4) Uani 1 1 d . . . H6B H 0.2839 0.3058 0.4635 0.047 Uiso 1 1 calc R . . C7B C 0.38413(18) 0.32002(14) 0.36819(17) 0.0440(5) Uani 1 1 d . . . H7B H 0.4116 0.3692 0.3957 0.053 Uiso 1 1 calc R . . C8B C 0.41761(16) 0.28660(14) 0.28874(16) 0.0405(5) Uani 1 1 d . . . H8B H 0.4683 0.3129 0.2617 0.049 Uiso 1 1 calc R . . C9B C 0.37828(13) 0.21349(13) 0.24578(14) 0.0322(4) Uani 1 1 d . . . C10B C 0.40644(14) 0.18030(13) 0.15793(15) 0.0356(4) Uani 1 1 d . . . H10B H 0.4591 0.2056 0.1324 0.043 Uiso 1 1 calc R . . C11B C 0.35997(14) 0.11307(13) 0.10918(14) 0.0339(4) Uani 1 1 d . . . H11B H 0.3774 0.0930 0.0481 0.041 Uiso 1 1 calc R . . C12B C 0.28559(14) 0.07346(11) 0.15016(13) 0.0275(3) Uani 1 1 d . . . C13B C 0.21555(15) 0.00331(12) 0.10489(13) 0.0294(3) Uani 1 1 d . . . C14B C 0.35079(14) -0.05627(11) 0.36960(12) 0.0268(3) Uani 1 1 d . . . C15B C 0.32283(16) -0.13020(11) 0.33242(13) 0.0304(4) Uani 1 1 d . . . H14B H 0.2508 -0.1515 0.3264 0.037 Uiso 1 1 calc R . . C16B C 0.40192(17) -0.17276(12) 0.30404(14) 0.0356(4) Uani 1 1 d . . . H15B H 0.3832 -0.2232 0.2779 0.043 Uiso 1 1 calc R . . C17B C 0.50784(17) -0.14215(14) 0.31362(14) 0.0398(5) Uani 1 1 d . . . C18B C 0.53419(16) -0.06815(14) 0.35194(15) 0.0388(5) Uani 1 1 d . . . H17B H 0.6066 -0.0471 0.3589 0.047 Uiso 1 1 calc R . . C19B C 0.45647(14) -0.02439(12) 0.38027(13) 0.0313(4) Uani 1 1 d . . . H18B H 0.4752 0.0261 0.4063 0.038 Uiso 1 1 calc R . . C20B C 0.5925(2) -0.19029(18) 0.28405(17) 0.0555(7) Uani 1 1 d . . . H19A H 0.6159 -0.2339 0.3357 0.083 Uiso 1 1 calc R . . H19B H 0.6613 -0.1602 0.2925 0.083 Uiso 1 1 calc R . . H19C H 0.5553 -0.2080 0.2048 0.083 Uiso 1 1 calc R . . C21B C 0.01918(13) 0.05278(10) 0.09208(14) 0.0264(3) Uani 1 1 d . . . H20C H -0.0222 0.0677 0.1416 0.032 Uiso 1 1 calc R . . H20D H 0.0437 0.0996 0.0648 0.032 Uiso 1 1 calc R . . C22B C -0.06358(14) 0.00962(10) -0.00991(15) 0.0272(3) Uani 1 1 d . . . C23B C -0.18921(14) 0.01290(11) -0.21448(15) 0.0304(3) Uani 1 1 d . . . H22B H -0.2486 -0.0154 -0.1952 0.036 Uiso 1 1 calc R . . C24B C -0.24955(14) 0.07491(12) -0.29774(14) 0.0309(4) Uani 1 1 d . . . C25B C -0.18643(16) 0.12844(12) -0.33028(14) 0.0327(4) Uani 1 1 d . . . H24B H -0.1039 0.1265 -0.2985 0.039 Uiso 1 1 calc R . . C26B C -0.2427(2) 0.18487(14) -0.40886(16) 0.0449(5) Uani 1 1 d . . . H25B H -0.1984 0.2215 -0.4292 0.054 Uiso 1 1 calc R . . C27B C -0.3630(2) 0.18767(17) -0.45748(18) 0.0597(8) Uani 1 1 d . . . H26B H -0.4014 0.2257 -0.5120 0.072 Uiso 1 1 calc R . . C28B C -0.4266(2) 0.13488(19) -0.42617(19) 0.0601(8) Uani 1 1 d . . . H27B H -0.5091 0.1368 -0.4593 0.072 Uiso 1 1 calc R . . C29B C -0.37096(16) 0.07859(15) -0.34615(18) 0.0452(6) Uani 1 1 d . . . H28B H -0.4157 0.0428 -0.3247 0.054 Uiso 1 1 calc R . . C30B C -0.1273(2) -0.04269(13) -0.26456(19) 0.0440(5) Uani 1 1 d . . . H29D H -0.0659 -0.0162 -0.2800 0.066 Uiso 1 1 calc R . . H29E H -0.1834 -0.0639 -0.3360 0.066 Uiso 1 1 calc R . . H29F H -0.0928 -0.0836 -0.2097 0.066 Uiso 1 1 calc R . . H1NA H 0.9460(17) 0.2015(15) 0.1948(17) 0.029(5) Uiso 1 1 d . . . H2NA H 1.0193(18) 0.2637(13) 0.1663(16) 0.025(5) Uiso 1 1 d . . . H3NA H 1.0907(18) 0.3401(15) -0.0483(19) 0.032(6) Uiso 1 1 d . . . H1NB H 0.1818(19) 0.0044(15) 0.0260(19) 0.036(6) Uiso 1 1 d . . . H2NB H 0.2683(17) -0.0407(13) 0.1273(16) 0.026(5) Uiso 1 1 d . . . H3NB H -0.072(2) 0.0918(15) -0.1097(19) 0.038(6) Uiso 1 1 d . . . N1A N 0.74699(10) 0.27076(8) 0.01732(10) 0.0188(2) Uani 1 1 d . . . N2A N 1.09600(11) 0.29631(8) -0.05996(11) 0.0200(2) Uani 1 1 d . . . N1B N 0.18695(11) 0.05272(9) 0.27005(11) 0.0233(3) Uani 1 1 d . . . N2B N -0.10446(11) 0.04651(8) -0.10871(12) 0.0237(2) Uani 1 1 d . . . O1A O 1.00786(10) 0.18340(7) -0.08574(9) 0.0239(2) Uani 1 1 d . . . O2A O 0.64145(10) 0.16124(8) -0.09991(9) 0.0280(3) Uani 1 1 d . . . O3A O 0.54674(9) 0.23981(8) 0.00195(9) 0.0260(2) Uani 1 1 d . . . O1B O -0.09515(13) -0.05529(8) 0.00056(14) 0.0443(3) Uani 1 1 d . . . O2B O 0.15286(12) -0.04572(9) 0.39355(11) 0.0364(3) Uani 1 1 d . . . O3B O 0.30140(12) 0.05331(8) 0.48069(10) 0.0341(3) Uani 1 1 d . . . S1 S 0.64825(3) 0.20302(2) -0.00056(3) 0.02021(7) Uani 1 1 d . . . S2 S 0.24484(3) 0.00133(3) 0.38963(3) 0.02672(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0160(5) 0.0210(7) 0.0210(5) 0.0023(5) 0.0102(4) 0.0014(5) C3A 0.0182(6) 0.0223(8) 0.0188(6) 0.0005(5) 0.0089(5) -0.0003(5) C4A 0.0197(6) 0.0217(8) 0.0230(6) 0.0003(5) 0.0105(5) 0.0008(5) C5A 0.0204(6) 0.0275(9) 0.0292(7) 0.0008(6) 0.0105(5) 0.0023(5) C6A 0.0232(7) 0.0312(10) 0.0401(9) 0.0030(7) 0.0129(6) 0.0061(6) C7A 0.0383(9) 0.0298(10) 0.0494(10) -0.0025(8) 0.0256(8) 0.0089(8) C8A 0.0408(9) 0.0321(11) 0.0362(8) -0.0079(7) 0.0213(7) 0.0009(7) C9A 0.0302(7) 0.0262(9) 0.0271(7) -0.0035(6) 0.0155(6) -0.0001(6) C10A 0.0328(8) 0.0327(10) 0.0216(6) -0.0065(6) 0.0113(6) -0.0039(7) C11A 0.0236(7) 0.0328(10) 0.0196(6) 0.0005(6) 0.0063(5) -0.0021(6) C12A 0.0192(6) 0.0227(8) 0.0194(6) 0.0025(5) 0.0080(5) 0.0003(5) C13A 0.0179(6) 0.0263(8) 0.0213(6) 0.0042(6) 0.0078(5) 0.0025(5) C14A 0.0187(6) 0.0239(8) 0.0231(6) -0.0006(5) 0.0112(5) -0.0038(5) C15A 0.0236(7) 0.0236(9) 0.0308(7) -0.0039(6) 0.0117(6) -0.0041(5) C16A 0.0335(9) 0.0229(9) 0.0429(9) 0.0002(7) 0.0166(7) -0.0010(6) C17A 0.0300(8) 0.0328(10) 0.0352(8) 0.0085(7) 0.0151(7) 0.0010(7) C18A 0.0323(8) 0.0396(11) 0.0256(7) 0.0055(7) 0.0156(6) 0.0046(7) C19A 0.0264(7) 0.0298(9) 0.0265(7) 0.0008(6) 0.0153(6) 0.0022(6) C20A 0.0474(11) 0.0498(14) 0.0425(10) 0.0190(10) 0.0143(9) 0.0070(10) C21A 0.0180(6) 0.0213(7) 0.0232(6) 0.0046(5) 0.0110(5) 0.0023(5) C22A 0.0180(6) 0.0176(7) 0.0177(5) 0.0011(5) 0.0090(4) -0.0006(5) C23A 0.0188(6) 0.0176(7) 0.0294(7) 0.0040(5) 0.0140(5) 0.0034(5) C24A 0.0240(7) 0.0245(8) 0.0291(7) 0.0046(6) 0.0177(6) 0.0038(5) C25A 0.0348(8) 0.0301(10) 0.0338(8) 0.0037(7) 0.0186(7) 0.0088(7) C26A 0.0515(11) 0.0396(12) 0.0390(9) -0.0049(8) 0.0261(9) 0.0043(9) C27A 0.0482(11) 0.0603(16) 0.0302(8) 0.0029(9) 0.0206(8) 0.0038(10) C28A 0.0455(11) 0.0640(16) 0.0302(8) 0.0164(9) 0.0208(8) 0.0160(10) C29A 0.0389(9) 0.0400(11) 0.0315(8) 0.0117(7) 0.0211(7) 0.0141(8) C30A 0.0189(6) 0.0276(9) 0.0433(9) 0.0077(7) 0.0141(6) 0.0007(6) C1B 0.0250(7) 0.0248(8) 0.0252(6) 0.0064(6) 0.0106(5) 0.0090(6) C3B 0.0195(6) 0.0325(9) 0.0214(6) 0.0101(6) 0.0099(5) 0.0085(6) C4B 0.0201(6) 0.0348(10) 0.0212(6) 0.0107(6) 0.0062(5) 0.0073(6) C5B 0.0302(7) 0.0337(10) 0.0238(6) 0.0063(6) 0.0086(5) 0.0069(7) C6B 0.0433(10) 0.0381(12) 0.0267(8) 0.0056(7) 0.0045(7) 0.0070(8) C7B 0.0417(10) 0.0411(13) 0.0336(9) 0.0087(8) -0.0026(7) -0.0046(8) C8B 0.0276(8) 0.0489(14) 0.0352(9) 0.0152(8) 0.0015(7) -0.0052(8) C9B 0.0201(6) 0.0450(12) 0.0269(7) 0.0139(7) 0.0041(5) 0.0025(7) C10B 0.0194(7) 0.0570(13) 0.0322(8) 0.0190(8) 0.0120(6) 0.0071(7) C11B 0.0252(7) 0.0551(13) 0.0269(7) 0.0145(7) 0.0161(6) 0.0133(7) C12B 0.0244(7) 0.0395(10) 0.0208(6) 0.0103(6) 0.0111(5) 0.0127(6) C13B 0.0311(8) 0.0374(10) 0.0211(6) 0.0066(6) 0.0116(6) 0.0139(7) C14B 0.0296(7) 0.0313(9) 0.0203(6) 0.0075(6) 0.0106(5) 0.0130(6) C15B 0.0352(8) 0.0324(10) 0.0234(7) 0.0081(6) 0.0109(6) 0.0121(7) C16B 0.0440(10) 0.0362(11) 0.0220(7) 0.0038(7) 0.0079(7) 0.0186(8) C17B 0.0361(9) 0.0586(15) 0.0212(7) 0.0007(7) 0.0072(6) 0.0244(9) C18B 0.0252(8) 0.0603(15) 0.0298(8) -0.0010(8) 0.0095(6) 0.0130(8) C19B 0.0264(7) 0.0423(11) 0.0236(7) 0.0008(7) 0.0080(6) 0.0089(7) C20B 0.0445(11) 0.086(2) 0.0310(9) -0.0132(10) 0.0094(8) 0.0323(12) C21B 0.0242(7) 0.0227(8) 0.0306(7) 0.0066(6) 0.0088(6) 0.0070(6) C22B 0.0248(7) 0.0170(8) 0.0397(8) 0.0051(6) 0.0124(6) 0.0033(5) C23B 0.0255(7) 0.0239(9) 0.0395(8) -0.0101(7) 0.0101(6) -0.0071(6) C24B 0.0227(7) 0.0349(10) 0.0296(7) -0.0137(7) 0.0040(6) 0.0026(6) C25B 0.0331(8) 0.0327(10) 0.0277(7) -0.0057(7) 0.0066(6) 0.0086(7) C26B 0.0608(13) 0.0398(13) 0.0278(8) -0.0022(8) 0.0102(8) 0.0175(9) C27B 0.0657(15) 0.0621(19) 0.0300(9) -0.0098(10) -0.0050(9) 0.0328(14) C28B 0.0339(10) 0.081(2) 0.0426(11) -0.0294(12) -0.0106(9) 0.0244(12) C29B 0.0241(8) 0.0584(15) 0.0434(10) -0.0269(10) 0.0024(7) 0.0016(8) C30B 0.0520(12) 0.0297(12) 0.0488(11) -0.0111(9) 0.0179(9) 0.0047(9) N1A 0.0147(5) 0.0236(7) 0.0206(5) -0.0006(4) 0.0096(4) -0.0005(4) N2A 0.0205(5) 0.0138(6) 0.0303(6) -0.0009(5) 0.0148(5) 0.0000(4) N1B 0.0243(6) 0.0268(7) 0.0220(5) 0.0090(5) 0.0124(5) 0.0081(5) N2B 0.0220(6) 0.0157(7) 0.0310(6) -0.0018(5) 0.0077(5) -0.0022(5) O1A 0.0291(5) 0.0169(6) 0.0309(5) -0.0032(4) 0.0175(4) -0.0050(4) O2A 0.0291(5) 0.0339(7) 0.0225(5) -0.0072(5) 0.0115(4) -0.0085(5) O3A 0.0169(5) 0.0350(7) 0.0282(5) 0.0031(5) 0.0110(4) -0.0002(4) O1B 0.0484(8) 0.0176(7) 0.0626(9) 0.0108(6) 0.0169(7) -0.0041(6) O2B 0.0387(7) 0.0408(8) 0.0399(7) 0.0179(6) 0.0266(6) 0.0117(6) O3B 0.0472(7) 0.0371(8) 0.0219(5) 0.0075(5) 0.0176(5) 0.0162(6) S1 0.01666(13) 0.02579(19) 0.02000(14) -0.00162(13) 0.00910(11) -0.00319(13) S2 0.03153(19) 0.0308(2) 0.02352(16) 0.01092(15) 0.01694(14) 0.01269(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A N1A 1.5072(17) . ? C1A C21A 1.5273(19) . ? C1A C13A 1.546(2) . ? C3A C12A 1.3809(19) . ? C3A C4A 1.418(2) . ? C3A N1A 1.4448(19) . ? C4A C5A 1.422(2) . ? C4A C9A 1.429(2) . ? C5A C6A 1.372(2) . ? C6A C7A 1.419(3) . ? C7A C8A 1.367(3) . ? C8A C9A 1.426(2) . ? C9A C10A 1.424(2) . ? C10A C11A 1.368(2) . ? C11A C12A 1.406(2) . ? C12A C13A 1.507(2) . ? C14A C15A 1.393(2) . ? C14A C19A 1.396(2) . ? C14A S1 1.7621(16) . ? C15A C16A 1.397(3) . ? C16A C17A 1.389(3) . ? C17A C18A 1.396(3) . ? C17A C20A 1.511(3) . ? C18A C19A 1.387(2) . ? C21A C22A 1.5214(19) . ? C22A O1A 1.2305(19) . ? C22A N2A 1.3332(18) . ? C23A N2A 1.4605(18) . ? C23A C24A 1.518(2) . ? C23A C30A 1.529(2) . ? C24A C29A 1.389(2) . ? C24A C25A 1.390(2) . ? C25A C26A 1.387(3) . ? C26A C27A 1.384(3) . ? C27A C28A 1.383(3) . ? C28A C29A 1.390(3) . ? C1B N1B 1.505(2) . ? C1B C21B 1.530(2) . ? C1B C13B 1.546(2) . ? C3B C12B 1.386(2) . ? C3B C4B 1.409(3) . ? C3B N1B 1.450(2) . ? C4B C5B 1.418(2) . ? C4B C9B 1.436(2) . ? C5B C6B 1.373(3) . ? C6B C7B 1.418(3) . ? C7B C8B 1.365(3) . ? C8B C9B 1.416(3) . ? C9B C10B 1.418(3) . ? C10B C11B 1.362(3) . ? C11B C12B 1.412(2) . ? C12B C13B 1.499(3) . ? C14B C15B 1.388(3) . ? C14B C19B 1.392(3) . ? C14B S2 1.7636(16) . ? C15B C16B 1.395(2) . ? C16B C17B 1.390(3) . ? C17B C18B 1.391(3) . ? C17B C20B 1.513(3) . ? C18B C19B 1.392(2) . ? C21B C22B 1.512(2) . ? C22B O1B 1.238(2) . ? C22B N2B 1.327(2) . ? C23B N2B 1.474(2) . ? C23B C24B 1.506(3) . ? C23B C30B 1.532(3) . ? C24B C25B 1.392(3) . ? C24B C29B 1.399(2) . ? C25B C26B 1.393(3) . ? C26B C27B 1.386(4) . ? C27B C28B 1.380(4) . ? C28B C29B 1.399(4) . ? N1A S1 1.6704(13) . ? N1B S2 1.6727(13) . ? O2A S1 1.4339(12) . ? O3A S1 1.4354(12) . ? O2B S2 1.4341(15) . ? O3B S2 1.4302(15) . ? 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 N1A C1A C21A 107.78(11) . . ? N1A C1A C13A 105.08(11) . . ? C21A C1A C13A 112.61(12) . . ? C12A C3A C4A 122.45(13) . . ? C12A C3A N1A 111.10(13) . . ? C4A C3A N1A 126.33(12) . . ? C3A C4A C5A 124.32(13) . . ? C3A C4A C9A 116.47(13) . . ? C5A C4A C9A 119.14(14) . . ? C6A C5A C4A 120.37(15) . . ? C5A C6A C7A 120.83(16) . . ? C8A C7A C6A 119.85(17) . . ? C7A C8A C9A 121.20(16) . . ? C10A C9A C8A 121.64(15) . . ? C10A C9A C4A 119.78(15) . . ? C8A C9A C4A 118.51(15) . . ? C11A C10A C9A 121.38(14) . . ? C10A C11A C12A 119.50(14) . . ? C3A C12A C11A 119.95(14) . . ? C3A C12A C13A 110.21(13) . . ? C11A C12A C13A 129.84(13) . . ? C12A C13A C1A 102.48(11) . . ? C15A C14A C19A 120.59(15) . . ? C15A C14A S1 119.54(11) . . ? C19A C14A S1 119.77(13) . . ? C14A C15A C16A 119.28(15) . . ? C17A C16A C15A 120.88(18) . . ? C16A C17A C18A 118.78(16) . . ? C16A C17A C20A 120.35(19) . . ? C18A C17A C20A 120.84(18) . . ? C19A C18A C17A 121.36(16) . . ? C18A C19A C14A 119.08(16) . . ? C22A C21A C1A 111.46(12) . . ? O1A C22A N2A 121.99(13) . . ? O1A C22A C21A 121.43(13) . . ? N2A C22A C21A 116.52(13) . . ? N2A C23A C24A 110.95(12) . . ? N2A C23A C30A 108.11(13) . . ? C24A C23A C30A 112.65(13) . . ? C29A C24A C25A 118.88(15) . . ? C29A C24A C23A 120.62(15) . . ? C25A C24A C23A 120.50(14) . . ? C26A C25A C24A 120.70(17) . . ? C27A C26A C25A 120.10(19) . . ? C28A C27A C26A 119.62(18) . . ? C27A C28A C29A 120.36(19) . . ? C24A C29A C28A 120.33(18) . . ? N1B C1B C21B 105.21(13) . . ? N1B C1B C13B 104.88(13) . . ? C21B C1B C13B 111.83(13) . . ? C12B C3B C4B 123.00(15) . . ? C12B C3B N1B 110.12(16) . . ? C4B C3B N1B 126.44(13) . . ? C3B C4B C5B 124.68(16) . . ? C3B C4B C9B 116.23(15) . . ? C5B C4B C9B 118.96(18) . . ? C6B C5B C4B 120.71(18) . . ? C5B C6B C7B 120.2(2) . . ? C8B C7B C6B 120.3(2) . . ? C7B C8B C9B 121.34(19) . . ? C8B C9B C10B 121.75(17) . . ? C8B C9B C4B 118.45(18) . . ? C10B C9B C4B 119.77(19) . . ? C11B C10B C9B 121.77(16) . . ? C10B C11B C12B 119.44(16) . . ? C3B C12B C11B 119.37(18) . . ? C3B C12B C13B 110.82(14) . . ? C11B C12B C13B 129.72(16) . . ? C12B C13B C1B 101.51(14) . . ? C15B C14B C19B 121.27(16) . . ? C15B C14B S2 119.30(14) . . ? C19B C14B S2 119.10(15) . . ? C14B C15B C16B 119.10(18) . . ? C17B C16B C15B 120.7(2) . . ? C16B C17B C18B 119.06(17) . . ? C16B C17B C20B 119.4(2) . . ? C18B C17B C20B 121.5(2) . . ? C17B C18B C19B 121.30(19) . . ? C14B C19B C18B 118.53(19) . . ? C22B C21B C1B 112.96(14) . . ? O1B C22B N2B 122.38(17) . . ? O1B C22B C21B 121.16(16) . . ? N2B C22B C21B 116.37(15) . . ? N2B C23B C24B 109.35(14) . . ? N2B C23B C30B 109.66(14) . . ? C24B C23B C30B 111.91(16) . . ? C25B C24B C29B 118.6(2) . . ? C25B C24B C23B 121.08(15) . . ? C29B C24B C23B 120.3(2) . . ? C24B C25B C26B 120.87(19) . . ? C27B C26B C25B 120.2(3) . . ? C28B C27B C26B 119.5(2) . . ? C27B C28B C29B 120.7(2) . . ? C28B C29B C24B 120.0(2) . . ? C3A N1A C1A 105.24(10) . . ? C3A N1A S1 117.28(9) . . ? C1A N1A S1 113.54(10) . . ? C22A N2A C23A 120.54(13) . . ? C3B N1B C1B 104.52(11) . . ? C3B N1B S2 116.82(10) . . ? C1B N1B S2 114.49(11) . . ? C22B N2B C23B 122.58(15) . . ? O2A S1 O3A 120.02(7) . . ? O2A S1 N1A 106.21(6) . . ? O3A S1 N1A 106.39(7) . . ? O2A S1 C14A 108.49(8) . . ? O3A S1 C14A 108.37(7) . . ? N1A S1 C14A 106.60(6) . . ? O3B S2 O2B 119.81(8) . . ? O3B S2 N1B 106.66(8) . . ? O2B S2 N1B 106.03(7) . . ? O3B S2 C14B 108.93(8) . . ? O2B S2 C14B 108.90(9) . . ? N1B S2 C14B 105.60(7) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 33.45 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.505 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.050