# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Datong Song' _publ_contact_author_email dsong@chem.utoronto.ca _publ_section_title ; Ester hydrogenation catalyzed by Ru-CNN pincer complexes ; loop_ _publ_author_name D.Song Yu.Sun C.Koehler R.Tan V.Annibale # Attachment '- CIF.cif' data_1aHBr _database_code_depnum_ccdc_archive 'CCDC 824073' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H38 Br Cl3 N4' _chemical_formula_weight 604.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 31.4131(16) _cell_length_b 8.2264(4) _cell_length_c 11.8449(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3060.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5200 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.025 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 1.627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6196 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'Bruker Apex 2' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22490 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0850 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5200 _reflns_number_gt 3844 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0141P)^2^+0.3878P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.012(8) _refine_ls_number_reflns 5200 _refine_ls_number_parameters 320 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0682 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.193355(13) 0.05080(5) 0.78985(4) 0.03283(11) Uani 1 1 d . . . Cl1 Cl 0.09588(7) 0.3254(2) 0.58916(15) 0.1117(8) Uani 1 1 d . . . Cl2 Cl 0.05416(5) 0.03536(17) 0.66226(13) 0.0671(4) Uani 1 1 d . . . Cl3 Cl 0.08324(5) 0.27372(17) 0.82588(11) 0.0659(4) Uani 1 1 d . . . N1 N 0.03218(12) 0.4935(5) 0.2417(3) 0.0447(11) Uani 1 1 d . . . N2 N 0.10526(11) 0.5638(4) 0.0048(3) 0.0301(9) Uani 1 1 d . . . N3 N 0.18978(11) 0.5773(4) -0.0815(3) 0.0216(8) Uani 1 1 d . . . N4 N 0.23055(11) 0.4108(4) 0.0077(3) 0.0242(9) Uani 1 1 d . . . C1 C 0.02852(19) 0.2057(7) 0.3177(5) 0.077(2) Uani 1 1 d . . . H1A H 0.0078 0.1217 0.3384 0.116 Uiso 1 1 calc R . . H1B H 0.0458 0.2338 0.3837 0.116 Uiso 1 1 calc R . . H1C H 0.0470 0.1649 0.2574 0.116 Uiso 1 1 calc R . . C2 C 0.00498(15) 0.3566(6) 0.2764(5) 0.0572(14) Uani 1 1 d . . . H2B H -0.0131 0.3253 0.2115 0.069 Uiso 1 1 calc R . . H2C H -0.0142 0.3944 0.3374 0.069 Uiso 1 1 calc R . . C3 C 0.0301(2) 0.6448(9) 0.4230(5) 0.086(2) Uani 1 1 d . . . H3A H 0.0488 0.6918 0.4808 0.129 Uiso 1 1 calc R . . H3B H 0.0119 0.5620 0.4574 0.129 Uiso 1 1 calc R . . H3C H 0.0124 0.7306 0.3901 0.129 Uiso 1 1 calc R . . C4 C 0.05662(17) 0.5688(7) 0.3327(4) 0.0528(15) Uani 1 1 d . . . H4A H 0.0754 0.6532 0.2998 0.063 Uiso 1 1 calc R . . H4B H 0.0751 0.4852 0.3675 0.063 Uiso 1 1 calc R . . C5 C 0.05993(16) 0.4507(6) 0.1504(4) 0.0477(13) Uani 1 1 d . . . H5A H 0.0457 0.3673 0.1035 0.057 Uiso 1 1 calc R . . H5B H 0.0860 0.4011 0.1821 0.057 Uiso 1 1 calc R . . C6 C 0.07291(15) 0.5935(5) 0.0739(4) 0.0331(11) Uani 1 1 d . . . C7 C 0.05136(15) 0.7401(6) 0.0750(4) 0.0390(12) Uani 1 1 d . . . H7A H 0.0281 0.7570 0.1247 0.047 Uiso 1 1 calc R . . C8 C 0.06426(15) 0.8603(6) 0.0031(4) 0.0373(12) Uani 1 1 d . . . H8A H 0.0503 0.9628 0.0029 0.045 Uiso 1 1 calc R . . C9 C 0.09809(14) 0.8307(5) -0.0700(4) 0.0344(12) Uani 1 1 d . . . H9A H 0.1077 0.9123 -0.1208 0.041 Uiso 1 1 calc R . . C10 C 0.11714(14) 0.6812(5) -0.0668(3) 0.0271(11) Uani 1 1 d . . . C11 C 0.15335(13) 0.6396(5) -0.1455(3) 0.0280(11) Uani 1 1 d . . . H11A H 0.1438 0.5566 -0.2005 0.034 Uiso 1 1 calc R . . H11B H 0.1620 0.7378 -0.1881 0.034 Uiso 1 1 calc R . . C12 C 0.21745(15) 0.6692(5) -0.0173(4) 0.0295(11) Uani 1 1 d . . . H12A H 0.2184 0.7845 -0.0138 0.035 Uiso 1 1 calc R . . C13 C 0.24270(14) 0.5670(5) 0.0389(3) 0.0295(11) Uani 1 1 d . . . H13A H 0.2647 0.5954 0.0902 0.035 Uiso 1 1 calc R . . C14 C 0.19880(14) 0.4198(5) -0.0651(3) 0.0219(10) Uani 1 1 d . . . H14A H 0.1848 0.3304 -0.0997 0.026 Uiso 1 1 calc R . . C15 C 0.24797(14) 0.2590(4) 0.0522(3) 0.0244(10) Uani 1 1 d . . . C16 C 0.22366(14) 0.1748(5) 0.1310(4) 0.0267(11) Uani 1 1 d . . . C17 C 0.24112(16) 0.0296(5) 0.1717(4) 0.0353(11) Uani 1 1 d . . . H17A H 0.2256 -0.0321 0.2256 0.042 Uiso 1 1 calc R . . C18 C 0.27993(17) -0.0258(5) 0.1358(4) 0.0339(12) Uani 1 1 d . . . H18A H 0.2910 -0.1246 0.1651 0.041 Uiso 1 1 calc R . . C19 C 0.30307(15) 0.0607(5) 0.0574(4) 0.0338(11) Uani 1 1 d . . . H19A H 0.3299 0.0203 0.0331 0.041 Uiso 1 1 calc R . . C20 C 0.28778(14) 0.2075(5) 0.0129(4) 0.0285(11) Uani 1 1 d . . . C21 C 0.18074(14) 0.2293(5) 0.1711(4) 0.0342(12) Uani 1 1 d . . . H21A H 0.1753 0.3397 0.1388 0.041 Uiso 1 1 calc R . . C22 C 0.17853(17) 0.2434(5) 0.2989(4) 0.0536(14) Uani 1 1 d . . . H22A H 0.2013 0.3152 0.3255 0.080 Uiso 1 1 calc R . . H22B H 0.1820 0.1355 0.3328 0.080 Uiso 1 1 calc R . . H22C H 0.1509 0.2886 0.3208 0.080 Uiso 1 1 calc R . . C23 C 0.14629(16) 0.1135(6) 0.1246(4) 0.0508(14) Uani 1 1 d . . . H23A H 0.1479 0.1110 0.0420 0.076 Uiso 1 1 calc R . . H23B H 0.1181 0.1521 0.1477 0.076 Uiso 1 1 calc R . . H23C H 0.1510 0.0039 0.1544 0.076 Uiso 1 1 calc R . . C24 C 0.31392(15) 0.2991(5) -0.0737(4) 0.0349(12) Uani 1 1 d . . . H24A H 0.2970 0.3956 -0.0985 0.042 Uiso 1 1 calc R . . C25 C 0.35533(16) 0.3619(6) -0.0202(5) 0.0524(14) Uani 1 1 d . . . H25A H 0.3485 0.4315 0.0445 0.079 Uiso 1 1 calc R . . H25B H 0.3714 0.4246 -0.0762 0.079 Uiso 1 1 calc R . . H25C H 0.3725 0.2695 0.0053 0.079 Uiso 1 1 calc R . . C26 C 0.32249(16) 0.1954(5) -0.1770(4) 0.0439(14) Uani 1 1 d . . . H26A H 0.2955 0.1533 -0.2065 0.066 Uiso 1 1 calc R . . H26B H 0.3410 0.1043 -0.1562 0.066 Uiso 1 1 calc R . . H26C H 0.3365 0.2614 -0.2350 0.066 Uiso 1 1 calc R . . C27 C 0.09306(17) 0.1796(6) 0.6946(4) 0.0471(13) Uani 1 1 d . . . H27A H 0.1212 0.1231 0.6989 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0386(2) 0.0258(2) 0.0341(2) 0.0014(3) 0.0064(3) -0.0025(2) Cl1 0.1227(17) 0.1319(16) 0.0805(12) 0.0646(12) -0.0319(12) -0.0698(13) Cl2 0.0517(9) 0.0589(9) 0.0907(11) 0.0067(8) -0.0137(8) -0.0140(7) Cl3 0.0766(11) 0.0581(9) 0.0630(11) -0.0065(7) 0.0101(8) 0.0135(7) N1 0.028(2) 0.069(3) 0.037(2) 0.0061(19) 0.001(2) -0.005(2) N2 0.033(2) 0.033(2) 0.0248(19) 0.0072(19) -0.0021(18) 0.0030(19) N3 0.024(2) 0.0158(19) 0.0248(19) 0.0045(15) -0.0003(17) 0.0034(17) N4 0.031(2) 0.0133(19) 0.028(2) 0.0021(15) -0.0023(19) 0.0038(16) C1 0.078(4) 0.083(5) 0.069(5) 0.026(3) 0.000(4) -0.033(4) C2 0.050(3) 0.071(3) 0.051(3) 0.018(3) 0.023(3) -0.012(3) C3 0.056(4) 0.133(6) 0.069(4) -0.029(4) 0.010(4) -0.004(4) C4 0.039(3) 0.085(4) 0.034(3) 0.003(3) 0.005(3) -0.006(3) C5 0.050(3) 0.056(3) 0.037(3) 0.010(3) 0.008(3) 0.000(3) C6 0.032(3) 0.039(3) 0.029(3) 0.006(2) 0.000(2) -0.002(2) C7 0.029(3) 0.047(3) 0.041(3) -0.002(3) 0.005(3) 0.002(2) C8 0.036(3) 0.032(3) 0.044(3) 0.001(2) 0.004(3) 0.005(2) C9 0.031(3) 0.028(3) 0.044(3) 0.010(2) 0.000(2) 0.000(2) C10 0.024(3) 0.032(3) 0.025(3) 0.003(2) -0.005(2) 0.001(2) C11 0.030(3) 0.025(3) 0.028(2) 0.004(2) -0.003(2) 0.001(2) C12 0.032(3) 0.021(2) 0.035(3) 0.001(2) -0.007(2) 0.001(2) C13 0.029(3) 0.023(3) 0.037(3) -0.008(2) -0.007(2) -0.002(2) C14 0.027(3) 0.012(2) 0.026(2) 0.0012(17) -0.002(2) -0.0015(19) C15 0.031(3) 0.015(2) 0.027(2) 0.006(2) -0.009(2) 0.002(2) C16 0.032(3) 0.020(2) 0.028(3) 0.000(2) -0.008(2) 0.002(2) C17 0.049(3) 0.028(3) 0.029(3) 0.007(2) 0.000(2) -0.005(2) C18 0.052(4) 0.015(2) 0.035(3) 0.011(2) -0.016(3) 0.000(2) C19 0.037(3) 0.022(2) 0.042(3) 0.005(2) -0.009(2) 0.008(2) C20 0.033(3) 0.019(2) 0.034(3) 0.001(2) -0.012(2) 0.002(2) C21 0.044(3) 0.023(2) 0.036(3) 0.011(2) 0.001(2) 0.005(2) C22 0.082(4) 0.036(3) 0.043(3) 0.009(3) 0.006(4) 0.018(2) C23 0.043(3) 0.039(3) 0.071(4) 0.002(3) 0.005(3) -0.008(2) C24 0.032(3) 0.024(3) 0.049(3) 0.009(2) -0.002(2) 0.008(2) C25 0.043(3) 0.047(3) 0.068(4) 0.002(3) 0.000(3) -0.004(3) C26 0.050(3) 0.036(3) 0.046(4) 0.004(2) 0.002(2) 0.010(2) C27 0.045(3) 0.053(3) 0.044(3) 0.008(3) 0.000(3) -0.009(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 Cl1 C27 1.734(5) . ? Cl2 C27 1.746(5) . ? Cl3 C27 1.764(5) . ? N1 C5 1.433(6) . ? N1 C4 1.461(6) . ? N1 C2 1.472(5) . ? N2 C6 1.328(5) . ? N2 C10 1.339(5) . ? N3 C14 1.340(5) . ? N3 C12 1.380(5) . ? N3 C11 1.465(5) . ? N4 C14 1.320(5) . ? N4 C13 1.391(5) . ? N4 C15 1.462(5) . ? C1 C2 1.525(7) . ? C3 C4 1.492(7) . ? C5 C6 1.538(6) . ? C6 C7 1.383(6) . ? C7 C8 1.366(6) . ? C8 C9 1.392(6) . ? C9 C10 1.368(6) . ? C10 C11 1.510(6) . ? C12 C13 1.333(6) . ? C15 C16 1.391(5) . ? C15 C20 1.400(6) . ? C16 C17 1.400(6) . ? C16 C21 1.499(6) . ? C17 C18 1.369(6) . ? C18 C19 1.377(6) . ? C19 C20 1.402(5) . ? C20 C24 1.515(6) . ? C21 C22 1.519(6) . ? C21 C23 1.544(6) . ? C24 C26 1.516(6) . ? C24 C25 1.537(6) . ? 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 C5 N1 C4 109.9(4) . . ? C5 N1 C2 112.1(4) . . ? C4 N1 C2 115.1(4) . . ? C6 N2 C10 118.1(4) . . ? C14 N3 C12 108.4(3) . . ? C14 N3 C11 125.3(3) . . ? C12 N3 C11 125.9(3) . . ? C14 N4 C13 109.2(3) . . ? C14 N4 C15 124.5(3) . . ? C13 N4 C15 126.2(4) . . ? N1 C2 C1 115.5(4) . . ? N1 C4 C3 114.4(5) . . ? N1 C5 C6 114.7(4) . . ? N2 C6 C7 122.7(4) . . ? N2 C6 C5 115.2(4) . . ? C7 C6 C5 122.1(4) . . ? C8 C7 C6 118.7(5) . . ? C7 C8 C9 119.2(4) . . ? C10 C9 C8 118.3(4) . . ? N2 C10 C9 123.0(4) . . ? N2 C10 C11 115.9(4) . . ? C9 C10 C11 121.1(4) . . ? N3 C11 C10 110.4(3) . . ? C13 C12 N3 107.7(4) . . ? C12 C13 N4 106.7(4) . . ? N4 C14 N3 108.0(3) . . ? C16 C15 C20 124.3(4) . . ? C16 C15 N4 117.5(4) . . ? C20 C15 N4 118.2(4) . . ? C15 C16 C17 116.2(4) . . ? C15 C16 C21 123.9(4) . . ? C17 C16 C21 119.9(4) . . ? C18 C17 C16 121.7(4) . . ? C17 C18 C19 120.5(4) . . ? C18 C19 C20 121.2(5) . . ? C15 C20 C19 116.2(4) . . ? C15 C20 C24 124.0(4) . . ? C19 C20 C24 119.8(4) . . ? C16 C21 C22 112.3(4) . . ? C16 C21 C23 109.4(4) . . ? C22 C21 C23 111.8(4) . . ? C20 C24 C26 111.3(4) . . ? C20 C24 C25 110.3(4) . . ? C26 C24 C25 111.8(4) . . ? Cl1 C27 Cl2 110.4(3) . . ? Cl1 C27 Cl3 109.9(3) . . ? Cl2 C27 Cl3 111.7(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.305 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.059 #===>END data_1bHBr _database_code_depnum_ccdc_archive 'CCDC 824074' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 Br N4' _chemical_formula_weight 443.43 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' Br Br -0.2901 2.4595 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9717(2) _cell_length_b 27.7991(8) _cell_length_c 9.8235(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.4310(10) _cell_angle_gamma 90.00 _cell_volume 2324.36(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 17718 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.00 _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.135 _exptl_crystal_size_min 0.0875 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.783 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6446 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'Bruker Apex 2' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17718 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4087 _reflns_number_gt 3402 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0302P)^2^+1.1361P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4087 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0694 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 Br1 Br 0.84089(2) 0.052738(9) 0.21893(2) 0.02624(8) Uani 1 1 d . . . N1 N 1.0619(3) 0.26239(8) -0.2832(2) 0.0501(6) Uani 1 1 d . . . N2 N 1.0391(2) 0.14131(7) -0.13813(19) 0.0277(4) Uani 1 1 d . . . N3 N 1.1813(2) 0.05873(7) 0.04860(18) 0.0213(4) Uani 1 1 d . . . N4 N 1.35356(19) 0.07114(7) 0.25571(18) 0.0210(4) Uani 1 1 d . . . C1 C 0.7813(4) 0.28524(14) -0.3833(4) 0.0741(11) Uani 1 1 d . . . H1A H 0.7096 0.3128 -0.3997 0.111 Uiso 1 1 calc R A . H1B H 0.7507 0.2614 -0.3235 0.111 Uiso 1 1 calc R . . H1C H 0.7759 0.2707 -0.4756 0.111 Uiso 1 1 calc R . . C2 C 0.9472(4) 0.30199(10) -0.3079(3) 0.0589(9) Uani 1 1 d . . . H2A H 0.9757 0.3271 -0.3666 0.071 Uiso 1 1 calc R . . H2B H 0.9521 0.3165 -0.2146 0.071 Uiso 1 1 calc R . . C3 C 1.3307(9) 0.2426(3) -0.2085(9) 0.072(2) Uiso 0.50 1 d P A 1 H3A H 1.4347 0.2572 -0.1670 0.107 Uiso 0.50 1 calc PR A 1 H3B H 1.3224 0.2288 -0.3024 0.107 Uiso 0.50 1 calc PR A 1 H3C H 1.3163 0.2172 -0.1447 0.107 Uiso 0.50 1 calc PR A 1 C3A C 1.3485(8) 0.2400(3) -0.2718(8) 0.0588(18) Uiso 0.50 1 d P B 2 H3AA H 1.4534 0.2535 -0.2564 0.088 Uiso 0.50 1 calc PR B 2 H3AB H 1.3103 0.2255 -0.3675 0.088 Uiso 0.50 1 calc PR B 2 H3AC H 1.3535 0.2154 -0.1991 0.088 Uiso 0.50 1 calc PR B 2 C4 C 1.2008(9) 0.2821(3) -0.2268(9) 0.066(2) Uiso 0.50 1 d P A 1 H4A H 1.2089 0.2962 -0.1322 0.079 Uiso 0.50 1 calc PR A 1 H4B H 1.2158 0.3081 -0.2900 0.079 Uiso 0.50 1 calc PR A 1 C4A C 1.2386(8) 0.2792(3) -0.2603(8) 0.0486(17) Uiso 0.50 1 d P B 2 H4AA H 1.2372 0.3043 -0.3323 0.058 Uiso 0.50 1 calc PR B 2 H4AB H 1.2804 0.2942 -0.1642 0.058 Uiso 0.50 1 calc PR B 2 C5 C 1.0403(4) 0.22675(10) -0.1818(3) 0.0558(9) Uani 1 1 d . A . H5A H 0.9413 0.2339 -0.1613 0.067 Uiso 1 1 calc R . . H5B H 1.1277 0.2297 -0.0906 0.067 Uiso 1 1 calc R . . C6 C 1.0343(3) 0.17559(9) -0.2350(2) 0.0301(5) Uani 1 1 d . . . C7 C 1.0191(3) 0.16506(9) -0.3773(2) 0.0300(5) Uani 1 1 d . A . H7A H 1.0141 0.1902 -0.4441 0.036 Uiso 1 1 calc R . . C8 C 1.0114(3) 0.11779(9) -0.4198(2) 0.0292(5) Uani 1 1 d . . . H8A H 1.0013 0.1098 -0.5163 0.035 Uiso 1 1 calc R A . C9 C 1.0187(2) 0.08202(8) -0.3202(2) 0.0253(5) Uani 1 1 d . A . H9A H 1.0158 0.0490 -0.3462 0.030 Uiso 1 1 calc R . . C10 C 1.0303(2) 0.09554(8) -0.1818(2) 0.0208(5) Uani 1 1 d . . . C11 C 1.0320(2) 0.05808(8) -0.0705(2) 0.0227(5) Uani 1 1 d . A . H11A H 0.9439 0.0641 -0.0323 0.027 Uiso 1 1 calc R . . H11B H 1.0164 0.0259 -0.1158 0.027 Uiso 1 1 calc R . . C12 C 1.3240(3) 0.04280(9) 0.0408(2) 0.0292(6) Uani 1 1 d . . . H12A H 1.3428 0.0290 -0.0407 0.035 Uiso 1 1 calc R . . C13 C 1.4315(3) 0.05046(9) 0.1696(2) 0.0289(5) Uani 1 1 d . . . H13A H 1.5403 0.0431 0.1963 0.035 Uiso 1 1 calc R . . C14 C 1.2026(2) 0.07591(8) 0.1787(2) 0.0205(5) Uani 1 1 d . . . H14A H 1.1233 0.0895 0.2120 0.025 Uiso 1 1 calc R . . C15 C 1.4194(2) 0.08223(8) 0.4072(2) 0.0233(5) Uani 1 1 d . . . C16 C 1.5303(2) 0.11883(9) 0.4491(2) 0.0277(5) Uani 1 1 d . . . C17 C 1.5889(3) 0.12867(10) 0.5956(3) 0.0362(6) Uani 1 1 d . . . H17A H 1.6654 0.1533 0.6279 0.043 Uiso 1 1 calc R . . C18 C 1.5397(3) 0.10379(11) 0.6957(3) 0.0387(6) Uani 1 1 d . . . C19 C 1.4312(3) 0.06706(10) 0.6479(2) 0.0342(6) Uani 1 1 d . . . H19A H 1.3978 0.0496 0.7161 0.041 Uiso 1 1 calc R . . C20 C 1.3697(2) 0.05494(9) 0.5038(2) 0.0271(5) Uani 1 1 d . . . C21 C 1.5888(3) 0.14616(9) 0.3437(3) 0.0354(6) Uani 1 1 d . . . H21A H 1.6399 0.1759 0.3884 0.053 Uiso 1 1 calc R . . H21B H 1.5000 0.1540 0.2585 0.053 Uiso 1 1 calc R . . H21C H 1.6645 0.1263 0.3155 0.053 Uiso 1 1 calc R . . C22 C 1.6022(3) 0.11634(14) 0.8534(3) 0.0599(9) Uani 1 1 d . . . H22A H 1.6322 0.0868 0.9099 0.090 Uiso 1 1 calc R . . H22B H 1.5206 0.1331 0.8818 0.090 Uiso 1 1 calc R . . H22C H 1.6943 0.1372 0.8707 0.090 Uiso 1 1 calc R . . C23 C 1.2572(3) 0.01363(9) 0.4565(2) 0.0321(6) Uani 1 1 d . . . H23A H 1.2913 -0.0071 0.3912 0.048 Uiso 1 1 calc R . . H23B H 1.1517 0.0260 0.4068 0.048 Uiso 1 1 calc R . . H23C H 1.2551 -0.0050 0.5405 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01899(12) 0.03495(14) 0.02637(12) -0.00328(11) 0.00945(8) -0.00042(10) N1 0.0798(18) 0.0232(12) 0.0426(13) 0.0023(10) 0.0127(12) -0.0080(12) N2 0.0368(11) 0.0246(11) 0.0204(9) 0.0010(8) 0.0072(8) -0.0002(9) N3 0.0199(9) 0.0237(10) 0.0214(9) 0.0040(8) 0.0079(7) 0.0004(8) N4 0.0182(9) 0.0241(10) 0.0215(9) 0.0018(8) 0.0075(8) 0.0003(8) C1 0.091(3) 0.073(3) 0.072(2) 0.015(2) 0.045(2) 0.023(2) C2 0.113(3) 0.0278(16) 0.0413(16) 0.0050(13) 0.0319(18) 0.0083(17) C5 0.109(3) 0.0247(15) 0.0281(14) 0.0006(12) 0.0142(15) -0.0004(16) C6 0.0382(13) 0.0242(13) 0.0253(12) 0.0000(10) 0.0062(10) -0.0015(10) C7 0.0395(13) 0.0266(13) 0.0225(11) 0.0062(10) 0.0078(10) -0.0027(11) C8 0.0362(13) 0.0335(15) 0.0185(11) -0.0028(10) 0.0096(10) -0.0034(11) C9 0.0285(12) 0.0222(13) 0.0255(12) -0.0021(10) 0.0088(9) -0.0011(10) C10 0.0164(10) 0.0233(13) 0.0214(11) 0.0008(9) 0.0039(8) -0.0019(9) C11 0.0180(10) 0.0261(13) 0.0225(11) 0.0010(10) 0.0041(9) -0.0023(9) C12 0.0235(12) 0.0395(16) 0.0278(12) -0.0028(11) 0.0125(10) 0.0039(10) C13 0.0202(11) 0.0378(14) 0.0306(12) 0.0010(11) 0.0106(9) 0.0043(10) C14 0.0179(11) 0.0230(12) 0.0217(11) 0.0034(9) 0.0081(9) 0.0001(9) C15 0.0174(10) 0.0293(13) 0.0228(11) 0.0004(10) 0.0058(9) 0.0046(10) C16 0.0192(11) 0.0290(14) 0.0349(13) -0.0017(11) 0.0084(9) 0.0031(10) C17 0.0213(12) 0.0436(17) 0.0399(14) -0.0115(12) 0.0042(10) -0.0017(11) C18 0.0289(13) 0.0570(19) 0.0270(13) -0.0042(12) 0.0042(10) 0.0106(13) C19 0.0273(13) 0.0513(18) 0.0247(12) 0.0066(11) 0.0092(10) 0.0074(12) C20 0.0193(11) 0.0349(14) 0.0277(12) 0.0054(11) 0.0083(9) 0.0073(10) C21 0.0306(13) 0.0306(15) 0.0469(15) -0.0021(12) 0.0149(11) -0.0062(11) C22 0.0475(17) 0.094(3) 0.0311(15) -0.0126(16) 0.0030(13) 0.0052(17) C23 0.0259(12) 0.0383(15) 0.0327(13) 0.0105(11) 0.0102(10) 0.0001(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C4 1.313(8) . ? N1 C5 1.461(3) . ? N1 C2 1.473(4) . ? N1 C4A 1.599(7) . ? N2 C10 1.337(3) . ? N2 C6 1.338(3) . ? N3 C14 1.321(3) . ? N3 C12 1.380(3) . ? N3 C11 1.474(3) . ? N4 C14 1.333(3) . ? N4 C13 1.381(3) . ? N4 C15 1.450(3) . ? C1 C2 1.512(5) . ? C3 C4 1.569(11) . ? C3A C4A 1.498(10) . ? C5 C6 1.510(3) . ? C6 C7 1.393(3) . ? C7 C8 1.374(3) . ? C8 C9 1.382(3) . ? C9 C10 1.382(3) . ? C10 C11 1.507(3) . ? C12 C13 1.343(3) . ? C15 C16 1.391(3) . ? C15 C20 1.394(3) . ? C16 C17 1.395(3) . ? C16 C21 1.506(3) . ? C17 C18 1.383(4) . ? C18 C19 1.386(4) . ? C18 C22 1.512(3) . ? C19 C20 1.388(3) . ? C20 C23 1.503(3) . ? 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 N1 C5 107.9(4) . . ? C4 N1 C2 106.1(4) . . ? C5 N1 C2 112.5(2) . . ? C5 N1 C4A 116.2(3) . . ? C2 N1 C4A 114.4(3) . . ? C10 N2 C6 117.68(18) . . ? C14 N3 C12 108.49(18) . . ? C14 N3 C11 126.12(18) . . ? C12 N3 C11 125.37(18) . . ? C14 N4 C13 108.30(18) . . ? C14 N4 C15 124.93(17) . . ? C13 N4 C15 126.58(17) . . ? N1 C2 C1 112.2(3) . . ? N1 C4 C3 109.2(6) . . ? C3A C4A N1 115.0(5) . . ? N1 C5 C6 113.6(2) . . ? N2 C6 C7 122.4(2) . . ? N2 C6 C5 115.8(2) . . ? C7 C6 C5 121.8(2) . . ? C8 C7 C6 119.0(2) . . ? C7 C8 C9 119.1(2) . . ? C8 C9 C10 118.2(2) . . ? N2 C10 C9 123.6(2) . . ? N2 C10 C11 116.02(18) . . ? C9 C10 C11 120.4(2) . . ? N3 C11 C10 111.42(17) . . ? C13 C12 N3 107.4(2) . . ? C12 C13 N4 106.94(19) . . ? N3 C14 N4 108.86(18) . . ? C16 C15 C20 123.4(2) . . ? C16 C15 N4 118.69(19) . . ? C20 C15 N4 117.95(19) . . ? C15 C16 C17 116.7(2) . . ? C15 C16 C21 122.5(2) . . ? C17 C16 C21 120.7(2) . . ? C18 C17 C16 122.3(2) . . ? C17 C18 C19 118.4(2) . . ? C17 C18 C22 121.0(3) . . ? C19 C18 C22 120.7(3) . . ? C18 C19 C20 122.3(2) . . ? C19 C20 C15 116.9(2) . . ? C19 C20 C23 120.8(2) . . ? C15 C20 C23 122.3(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.288 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.051 #===> END data_2a _database_code_depnum_ccdc_archive 'CCDC 824075' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H37 Br N4 O Ru' _chemical_formula_weight 614.59 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' Br Br -0.2901 2.4595 '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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9037(5) _cell_length_b 16.1438(7) _cell_length_c 14.7255(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.140(2) _cell_angle_gamma 90.00 _cell_volume 2673.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 54156 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 36.97 _exptl_crystal_description block _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 2.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6779 _exptl_absorpt_correction_T_max 0.7568 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 54156 _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 36.97 _reflns_number_total 13497 _reflns_number_gt 8556 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0441P)^2^+0.2867P] 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 13497 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0957 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.561657(14) 0.178573(10) 0.278385(12) 0.01727(4) Uani 1 1 d . . . Br1 Br 0.60526(2) 0.235750(18) 0.121748(19) 0.03602(7) Uani 1 1 d . . . O1 O 0.63218(16) 0.33501(12) 0.38890(15) 0.0390(5) Uani 1 1 d . . . N1 N 0.73729(15) 0.11271(11) 0.34113(13) 0.0210(3) Uani 1 1 d . . . N2 N 0.52559(15) 0.06181(11) 0.20668(13) 0.0212(3) Uani 1 1 d . . . N3 N 0.31492(15) 0.16586(11) 0.14463(13) 0.0215(4) Uani 1 1 d . . . N4 N 0.31183(14) 0.24637(11) 0.25971(12) 0.0173(3) Uani 1 1 d . . . C1 C 0.8832(2) 0.19947(17) 0.2928(2) 0.0361(6) Uani 1 1 d . . . H1A H 0.9363 0.1986 0.2541 0.054 Uiso 1 1 calc R . . H1B H 0.9298 0.2097 0.3603 0.054 Uiso 1 1 calc R . . H1C H 0.8242 0.2436 0.2696 0.054 Uiso 1 1 calc R . . C2 C 0.82056(19) 0.11707(15) 0.28426(18) 0.0272(5) Uani 1 1 d . . . H2A H 0.7754 0.1066 0.2158 0.033 Uiso 1 1 calc R . . H2B H 0.8809 0.0728 0.3064 0.033 Uiso 1 1 calc R . . C3 C 0.9094(2) 0.08965(16) 0.49754(19) 0.0342(5) Uani 1 1 d . . . H3A H 0.9423 0.1107 0.5634 0.051 Uiso 1 1 calc R . . H3B H 0.9684 0.0959 0.4647 0.051 Uiso 1 1 calc R . . H3C H 0.8892 0.0309 0.4992 0.051 Uiso 1 1 calc R . . C4 C 0.79772(19) 0.13844(15) 0.44362(16) 0.0264(5) Uani 1 1 d . . . H4A H 0.7401 0.1330 0.4788 0.032 Uiso 1 1 calc R . . H4B H 0.8192 0.1978 0.4444 0.032 Uiso 1 1 calc R . . C5 C 0.6975(2) 0.02493(14) 0.34050(18) 0.0284(5) Uani 1 1 d . . . H5A H 0.6631 0.0169 0.3926 0.034 Uiso 1 1 calc R . . H5B H 0.7670 -0.0123 0.3531 0.034 Uiso 1 1 calc R . . C6 C 0.6066(2) 0.00235(14) 0.24614(18) 0.0257(4) Uani 1 1 d . . . C7 C 0.6020(2) -0.07487(15) 0.2040(2) 0.0354(6) Uani 1 1 d . . . H7A H 0.6615 -0.1152 0.2319 0.042 Uiso 1 1 calc R . . C8 C 0.5093(2) -0.09237(16) 0.1204(2) 0.0362(6) Uani 1 1 d . . . H8A H 0.5030 -0.1454 0.0911 0.043 Uiso 1 1 calc R . . C9 C 0.4264(2) -0.03168(16) 0.08058(19) 0.0311(5) Uani 1 1 d . . . H9A H 0.3622 -0.0425 0.0233 0.037 Uiso 1 1 calc R . . C10 C 0.43704(19) 0.04545(15) 0.12470(16) 0.0246(4) Uani 1 1 d . . . C11 C 0.3548(2) 0.11540(15) 0.07842(16) 0.0265(5) Uani 1 1 d . . . H11A H 0.3957 0.1519 0.0452 0.032 Uiso 1 1 calc R . . H11B H 0.2840 0.0920 0.0290 0.032 Uiso 1 1 calc R . . C12 C 0.19651(19) 0.18508(14) 0.12906(16) 0.0239(4) Uani 1 1 d . . . H12A H 0.1299 0.1661 0.0776 0.029 Uiso 1 1 calc R . . C13 C 0.19414(18) 0.23555(14) 0.20059(16) 0.0216(4) Uani 1 1 d . . . H13A H 0.1255 0.2594 0.2094 0.026 Uiso 1 1 calc R . . C14 C 0.38864(17) 0.20351(13) 0.22540(14) 0.0179(4) Uani 1 1 d . . . C15 C 0.34170(17) 0.29780(13) 0.34497(15) 0.0180(4) Uani 1 1 d . . . C16 C 0.35218(17) 0.26028(14) 0.43288(15) 0.0203(4) Uani 1 1 d . . . C17 C 0.37085(19) 0.31217(15) 0.51246(16) 0.0259(5) Uani 1 1 d . . . H17A H 0.3765 0.2888 0.5730 0.031 Uiso 1 1 calc R . . C18 C 0.3813(2) 0.39721(15) 0.50455(17) 0.0277(5) Uani 1 1 d . . . H18A H 0.3942 0.4315 0.5595 0.033 Uiso 1 1 calc R . . C19 C 0.37305(19) 0.43212(14) 0.41697(17) 0.0256(4) Uani 1 1 d . . . H19A H 0.3819 0.4903 0.4127 0.031 Uiso 1 1 calc R . . C20 C 0.35192(18) 0.38352(14) 0.33474(15) 0.0211(4) Uani 1 1 d . . . C21 C 0.34008(19) 0.16732(14) 0.44266(16) 0.0230(4) Uani 1 1 d . . . H21A H 0.3484 0.1405 0.3840 0.028 Uiso 1 1 calc R . . C22 C 0.2169(2) 0.14598(17) 0.4469(2) 0.0332(5) Uani 1 1 d . . . H22A H 0.1559 0.1689 0.3903 0.050 Uiso 1 1 calc R . . H22B H 0.2076 0.1697 0.5053 0.050 Uiso 1 1 calc R . . H22C H 0.2080 0.0857 0.4477 0.050 Uiso 1 1 calc R . . C23 C 0.4375(2) 0.13214(17) 0.53035(19) 0.0360(6) Uani 1 1 d . . . H23A H 0.5157 0.1464 0.5264 0.054 Uiso 1 1 calc R . . H23B H 0.4296 0.0718 0.5316 0.054 Uiso 1 1 calc R . . H23C H 0.4293 0.1558 0.5892 0.054 Uiso 1 1 calc R . . C24 C 0.3378(2) 0.42300(14) 0.23838(17) 0.0261(4) Uani 1 1 d . . . H24A H 0.3419 0.3782 0.1927 0.031 Uiso 1 1 calc R . . C25 C 0.2161(2) 0.46516(18) 0.1983(2) 0.0380(6) Uani 1 1 d . . . H25A H 0.1533 0.4248 0.1945 0.057 Uiso 1 1 calc R . . H25B H 0.2059 0.4869 0.1339 0.057 Uiso 1 1 calc R . . H25C H 0.2113 0.5108 0.2407 0.057 Uiso 1 1 calc R . . C26 C 0.4369(2) 0.48542(17) 0.2447(2) 0.0357(6) Uani 1 1 d . . . H26A H 0.5143 0.4579 0.2704 0.053 Uiso 1 1 calc R . . H26B H 0.4326 0.5311 0.2873 0.053 Uiso 1 1 calc R . . H26C H 0.4272 0.5072 0.1805 0.053 Uiso 1 1 calc R . . C27 C 0.60186(19) 0.27532(15) 0.34607(17) 0.0258(4) Uani 1 1 d . . . H1 H 0.540(3) 0.1348(18) 0.372(2) 0.043(8) 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 0.01584(7) 0.01901(7) 0.01865(7) -0.00040(6) 0.00795(5) 0.00112(6) Br1 0.03565(13) 0.04422(16) 0.03269(14) 0.01605(11) 0.01731(11) 0.00364(11) O1 0.0265(8) 0.0346(10) 0.0469(12) -0.0125(9) 0.0000(8) -0.0006(7) N1 0.0197(8) 0.0191(8) 0.0264(9) 0.0032(7) 0.0107(7) 0.0021(6) N2 0.0207(8) 0.0214(9) 0.0235(9) -0.0006(7) 0.0098(7) -0.0002(6) N3 0.0206(8) 0.0258(10) 0.0180(8) -0.0041(7) 0.0060(7) 0.0013(7) N4 0.0152(7) 0.0191(8) 0.0175(8) -0.0021(6) 0.0052(6) 0.0004(6) C1 0.0251(11) 0.0418(15) 0.0417(15) 0.0096(12) 0.0114(10) -0.0069(10) C2 0.0230(10) 0.0270(11) 0.0364(13) 0.0014(10) 0.0163(9) 0.0027(8) C3 0.0283(11) 0.0310(13) 0.0380(14) 0.0092(11) 0.0038(10) 0.0016(10) C4 0.0248(10) 0.0264(12) 0.0272(11) 0.0018(9) 0.0072(9) 0.0019(8) C5 0.0293(11) 0.0186(10) 0.0366(13) 0.0056(9) 0.0096(10) -0.0007(8) C6 0.0275(10) 0.0180(10) 0.0334(12) 0.0012(9) 0.0125(9) -0.0004(8) C7 0.0386(13) 0.0209(11) 0.0476(16) -0.0019(11) 0.0152(12) 0.0015(10) C8 0.0448(14) 0.0214(11) 0.0468(16) -0.0080(11) 0.0211(12) -0.0037(10) C9 0.0326(12) 0.0300(12) 0.0340(13) -0.0087(10) 0.0152(10) -0.0038(10) C10 0.0243(10) 0.0279(11) 0.0249(11) -0.0053(9) 0.0126(8) -0.0008(8) C11 0.0274(10) 0.0316(12) 0.0204(10) -0.0075(9) 0.0076(8) 0.0034(9) C12 0.0197(9) 0.0274(11) 0.0230(10) -0.0033(9) 0.0047(8) -0.0002(8) C13 0.0169(8) 0.0256(11) 0.0221(10) -0.0018(8) 0.0060(7) 0.0008(7) C14 0.0194(9) 0.0198(9) 0.0164(9) 0.0005(7) 0.0084(7) 0.0030(7) C15 0.0140(8) 0.0214(9) 0.0190(9) -0.0025(7) 0.0061(7) 0.0001(7) C16 0.0174(9) 0.0250(10) 0.0194(9) -0.0009(8) 0.0074(7) -0.0004(7) C17 0.0250(10) 0.0346(13) 0.0186(10) -0.0022(9) 0.0079(8) -0.0003(9) C18 0.0265(10) 0.0330(13) 0.0242(11) -0.0102(9) 0.0090(9) -0.0015(9) C19 0.0253(10) 0.0220(10) 0.0295(12) -0.0058(9) 0.0092(9) -0.0005(8) C20 0.0198(9) 0.0223(10) 0.0225(10) -0.0017(8) 0.0086(8) 0.0000(7) C21 0.0229(9) 0.0258(11) 0.0223(10) 0.0020(8) 0.0103(8) -0.0015(8) C22 0.0298(12) 0.0327(13) 0.0436(15) -0.0059(11) 0.0210(11) -0.0065(10) C23 0.0345(13) 0.0356(14) 0.0346(14) 0.0104(11) 0.0066(11) -0.0018(11) C24 0.0325(11) 0.0221(10) 0.0245(11) 0.0011(9) 0.0107(9) -0.0035(9) C25 0.0306(12) 0.0383(15) 0.0382(15) 0.0099(12) 0.0020(11) -0.0038(11) C26 0.0346(13) 0.0356(14) 0.0357(14) 0.0097(11) 0.0101(11) -0.0075(10) C27 0.0198(9) 0.0288(12) 0.0277(11) 0.0022(9) 0.0062(8) 0.0076(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 C27 1.830(2) . ? Ru1 C14 1.9896(19) . ? Ru1 N2 2.1343(18) . ? Ru1 N1 2.2557(17) . ? Ru1 Br1 2.6883(3) . ? Ru1 H1 1.65(3) . ? O1 C27 1.143(3) . ? N1 C5 1.493(3) . ? N1 C2 1.494(3) . ? N1 C4 1.502(3) . ? N2 C10 1.343(3) . ? N2 C6 1.350(3) . ? N3 C14 1.367(3) . ? N3 C12 1.387(3) . ? N3 C11 1.464(3) . ? N4 C14 1.369(2) . ? N4 C13 1.397(3) . ? N4 C15 1.449(3) . ? C1 C2 1.510(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.525(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.499(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.386(3) . ? C7 C8 1.386(4) . ? C7 H7A 0.9500 . ? C8 C9 1.378(4) . ? C8 H8A 0.9500 . ? C9 C10 1.391(3) . ? C9 H9A 0.9500 . ? C10 C11 1.504(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.339(3) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C15 C16 1.397(3) . ? C15 C20 1.402(3) . ? C16 C17 1.398(3) . ? C16 C21 1.519(3) . ? C17 C18 1.387(3) . ? C17 H17A 0.9500 . ? C18 C19 1.381(3) . ? C18 H18A 0.9500 . ? C19 C20 1.395(3) . ? C19 H19A 0.9500 . ? C20 C24 1.514(3) . ? C21 C22 1.527(3) . ? C21 C23 1.534(3) . ? C21 H21A 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C26 1.531(3) . ? C24 C25 1.533(3) . ? C24 H24A 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C27 Ru1 C14 95.34(9) . . ? C27 Ru1 N2 175.93(8) . . ? C14 Ru1 N2 88.29(8) . . ? C27 Ru1 N1 97.90(8) . . ? C14 Ru1 N1 163.17(8) . . ? N2 Ru1 N1 78.20(7) . . ? C27 Ru1 Br1 94.86(8) . . ? C14 Ru1 Br1 93.46(6) . . ? N2 Ru1 Br1 86.73(5) . . ? N1 Ru1 Br1 95.71(5) . . ? C27 Ru1 H1 89.7(10) . . ? C14 Ru1 H1 89.2(10) . . ? N2 Ru1 H1 88.6(10) . . ? N1 Ru1 H1 80.6(10) . . ? Br1 Ru1 H1 174.5(10) . . ? C5 N1 C2 107.98(18) . . ? C5 N1 C4 108.37(18) . . ? C2 N1 C4 111.28(17) . . ? C5 N1 Ru1 101.25(12) . . ? C2 N1 Ru1 116.38(14) . . ? C4 N1 Ru1 110.82(13) . . ? C10 N2 C6 119.1(2) . . ? C10 N2 Ru1 126.13(15) . . ? C6 N2 Ru1 114.57(15) . . ? C14 N3 C12 111.83(17) . . ? C14 N3 C11 124.81(17) . . ? C12 N3 C11 123.25(18) . . ? C14 N4 C13 111.20(17) . . ? C14 N4 C15 127.28(16) . . ? C13 N4 C15 121.52(16) . . ? 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 . . ? N1 C2 C1 113.3(2) . . ? N1 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? N1 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C3 115.4(2) . . ? N1 C4 H4A 108.4 . . ? C3 C4 H4A 108.4 . . ? N1 C4 H4B 108.4 . . ? C3 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? N1 C5 C6 111.56(19) . . ? N1 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N1 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? N2 C6 C7 122.0(2) . . ? N2 C6 C5 115.0(2) . . ? C7 C6 C5 123.0(2) . . ? C6 C7 C8 118.9(2) . . ? C6 C7 H7A 120.5 . . ? C8 C7 H7A 120.5 . . ? C9 C8 C7 118.9(2) . . ? C9 C8 H8A 120.5 . . ? C7 C8 H8A 120.5 . . ? C8 C9 C10 119.6(2) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? N2 C10 C9 121.4(2) . . ? N2 C10 C11 117.5(2) . . ? C9 C10 C11 121.0(2) . . ? N3 C11 C10 114.91(19) . . ? N3 C11 H11A 108.5 . . ? C10 C11 H11A 108.5 . . ? N3 C11 H11B 108.5 . . ? C10 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C13 C12 N3 106.76(19) . . ? C13 C12 H12A 126.6 . . ? N3 C12 H12A 126.6 . . ? C12 C13 N4 106.91(18) . . ? C12 C13 H13A 126.5 . . ? N4 C13 H13A 126.5 . . ? N3 C14 N4 103.29(16) . . ? N3 C14 Ru1 122.53(14) . . ? N4 C14 Ru1 133.51(15) . . ? C16 C15 C20 122.89(19) . . ? C16 C15 N4 118.45(19) . . ? C20 C15 N4 118.55(18) . . ? C15 C16 C17 117.3(2) . . ? C15 C16 C21 122.25(19) . . ? C17 C16 C21 120.4(2) . . ? C18 C17 C16 121.1(2) . . ? C18 C17 H17A 119.4 . . ? C16 C17 H17A 119.4 . . ? C19 C18 C17 120.1(2) . . ? C19 C18 H18A 119.9 . . ? C17 C18 H18A 119.9 . . ? C18 C19 C20 121.2(2) . . ? C18 C19 H19A 119.4 . . ? C20 C19 H19A 119.4 . . ? C19 C20 C15 117.3(2) . . ? C19 C20 C24 120.7(2) . . ? C15 C20 C24 121.98(19) . . ? C16 C21 C22 110.42(19) . . ? C16 C21 C23 112.13(19) . . ? C22 C21 C23 110.7(2) . . ? C16 C21 H21A 107.8 . . ? C22 C21 H21A 107.8 . . ? C23 C21 H21A 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 C26 111.92(19) . . ? C20 C24 C25 110.42(19) . . ? C26 C24 C25 110.1(2) . . ? C20 C24 H24A 108.1 . . ? C26 C24 H24A 108.1 . . ? C25 C24 H24A 108.1 . . ? 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 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O1 C27 Ru1 176.9(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 36.97 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.846 _refine_diff_density_min -1.258 _refine_diff_density_rms 0.128 #===> END data_2b _database_code_depnum_ccdc_archive 'CCDC 824076' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H31 Br N4 O Ru' _chemical_formula_weight 572.51 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' Br Br -0.2901 2.4595 '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 20.3638(4) _cell_length_b 10.1860(2) _cell_length_c 23.8259(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.6510(10) _cell_angle_gamma 90.00 _cell_volume 4856.96(17) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4283 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.125 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 2.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6175 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'Bruker Apex 2' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16273 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4283 _reflns_number_gt 3395 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0199P)^2^+5.1253P] 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 4283 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0566 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.247317(12) 0.48417(2) 0.355480(10) 0.01441(8) Uani 1 1 d . . . Br1 Br 0.174220(15) 0.50122(3) 0.437323(13) 0.02461(9) Uani 1 1 d . . . O1 O 0.29011(12) 0.7645(2) 0.36281(9) 0.0341(6) Uani 1 1 d . . . N1 N 0.16364(12) 0.5255(2) 0.28096(10) 0.0183(5) Uani 1 1 d . . . N2 N 0.20752(12) 0.2925(2) 0.33524(10) 0.0157(5) Uani 1 1 d . . . N3 N 0.31639(12) 0.2812(2) 0.43431(10) 0.0175(6) Uani 1 1 d . . . N4 N 0.38416(12) 0.4427(2) 0.43559(10) 0.0181(6) Uani 1 1 d . . . C1 C 0.08519(17) 0.6745(3) 0.32211(15) 0.0317(8) Uani 1 1 d . . . H1A H 0.0402 0.6778 0.3312 0.048 Uiso 1 1 calc R . . H1B H 0.0899 0.7438 0.2946 0.048 Uiso 1 1 calc R . . H1C H 0.1184 0.6876 0.3571 0.048 Uiso 1 1 calc R . . C2 C 0.09624(15) 0.5417(3) 0.29650(13) 0.0224(7) Uani 1 1 d . . . H2A H 0.0901 0.4724 0.3242 0.027 Uiso 1 1 calc R . . H2B H 0.0617 0.5285 0.2618 0.027 Uiso 1 1 calc R . . C3 C 0.13239(17) 0.6617(3) 0.18947(14) 0.0310(8) Uani 1 1 d . . . H3A H 0.1476 0.7375 0.1700 0.047 Uiso 1 1 calc R . . H3B H 0.0874 0.6788 0.1969 0.047 Uiso 1 1 calc R . . H3C H 0.1314 0.5837 0.1653 0.047 Uiso 1 1 calc R . . C4 C 0.18018(15) 0.6386(3) 0.24591(13) 0.0218(7) Uani 1 1 d . . . H4A H 0.2256 0.6245 0.2377 0.026 Uiso 1 1 calc R . . H4B H 0.1817 0.7194 0.2692 0.026 Uiso 1 1 calc R . . C5 C 0.16368(16) 0.4034(3) 0.24667(13) 0.0213(7) Uani 1 1 d . . . H5A H 0.2022 0.4052 0.2267 0.026 Uiso 1 1 calc R . . H5B H 0.1223 0.4000 0.2174 0.026 Uiso 1 1 calc R . . C6 C 0.16781(15) 0.2829(3) 0.28313(13) 0.0192(7) Uani 1 1 d . . . C7 C 0.13708(16) 0.1666(3) 0.26366(13) 0.0245(7) Uani 1 1 d . . . H7A H 0.1084 0.1626 0.2274 0.029 Uiso 1 1 calc R . . C8 C 0.14859(17) 0.0560(3) 0.29778(14) 0.0302(8) Uani 1 1 d . . . H8A H 0.1285 -0.0254 0.2848 0.036 Uiso 1 1 calc R . . C9 C 0.18927(16) 0.0647(3) 0.35061(13) 0.0237(7) Uani 1 1 d . . . H9A H 0.1981 -0.0107 0.3743 0.028 Uiso 1 1 calc R . . C10 C 0.21724(15) 0.1849(3) 0.36892(12) 0.0184(7) Uani 1 1 d . . . C11 C 0.25527(15) 0.2027(3) 0.42829(12) 0.0191(7) Uani 1 1 d . . . H11A H 0.2253 0.2443 0.4514 0.023 Uiso 1 1 calc R . . H11B H 0.2672 0.1148 0.4448 0.023 Uiso 1 1 calc R . . C12 C 0.37535(16) 0.2450(3) 0.46989(13) 0.0225(7) Uani 1 1 d . . . H12A H 0.3839 0.1642 0.4898 0.027 Uiso 1 1 calc R . . C13 C 0.41809(16) 0.3455(3) 0.47086(13) 0.0232(7) Uani 1 1 d . . . H13A H 0.4627 0.3497 0.4915 0.028 Uiso 1 1 calc R . . C14 C 0.32073(15) 0.4043(3) 0.41286(12) 0.0157(7) Uani 1 1 d . . . C15 C 0.41139(15) 0.5712(3) 0.43112(12) 0.0180(7) Uani 1 1 d . . . C16 C 0.45269(15) 0.5934(3) 0.39164(13) 0.0206(7) Uani 1 1 d . . . C17 C 0.47717(15) 0.7207(3) 0.38816(13) 0.0234(7) Uani 1 1 d . . . H17A H 0.5057 0.7386 0.3618 0.028 Uiso 1 1 calc R . . C18 C 0.46089(15) 0.8217(3) 0.42219(13) 0.0228(7) Uani 1 1 d . . . C19 C 0.42145(15) 0.7939(3) 0.46208(13) 0.0233(7) Uani 1 1 d . . . H19A H 0.4114 0.8622 0.4863 0.028 Uiso 1 1 calc R . . C20 C 0.39606(15) 0.6688(3) 0.46783(13) 0.0212(7) Uani 1 1 d . . . C21 C 0.47015(17) 0.4847(3) 0.35425(14) 0.0295(8) Uani 1 1 d . . . H21A H 0.4291 0.4476 0.3319 0.044 Uiso 1 1 calc R . . H21B H 0.4948 0.4159 0.3781 0.044 Uiso 1 1 calc R . . H21C H 0.4980 0.5197 0.3283 0.044 Uiso 1 1 calc R . . C22 C 0.48700(17) 0.9586(3) 0.41614(15) 0.0327(8) Uani 1 1 d . . . H22A H 0.4641 1.0204 0.4375 0.049 Uiso 1 1 calc R . . H22B H 0.4787 0.9835 0.3757 0.049 Uiso 1 1 calc R . . H22C H 0.5351 0.9610 0.4313 0.049 Uiso 1 1 calc R . . C23 C 0.35253(17) 0.6395(3) 0.51114(14) 0.0316(8) Uani 1 1 d . . . H23A H 0.3492 0.7179 0.5342 0.047 Uiso 1 1 calc R . . H23B H 0.3723 0.5676 0.5360 0.047 Uiso 1 1 calc R . . H23C H 0.3078 0.6138 0.4913 0.047 Uiso 1 1 calc R . . C24 C 0.27654(15) 0.6541(3) 0.36251(12) 0.0207(7) Uani 1 1 d . . . H1 H 0.3023(13) 0.461(2) 0.2979(11) 0.016(7) 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 0.01460(14) 0.01384(12) 0.01432(13) 0.00117(10) 0.00147(10) -0.00035(10) Br1 0.02617(19) 0.02719(18) 0.02275(18) 0.00285(13) 0.01050(14) 0.00336(13) O1 0.0385(16) 0.0187(12) 0.0386(15) 0.0067(10) -0.0101(12) -0.0057(10) N1 0.0187(14) 0.0170(12) 0.0190(13) 0.0034(10) 0.0031(11) -0.0016(10) N2 0.0150(14) 0.0156(12) 0.0172(14) -0.0006(10) 0.0047(11) 0.0003(10) N3 0.0184(14) 0.0178(13) 0.0153(14) 0.0020(10) 0.0010(11) 0.0003(10) N4 0.0209(15) 0.0160(12) 0.0163(14) 0.0023(10) 0.0007(11) 0.0012(10) C1 0.028(2) 0.0296(18) 0.040(2) 0.0086(15) 0.0142(17) 0.0100(15) C2 0.0150(17) 0.0245(16) 0.0268(18) 0.0070(13) 0.0018(14) -0.0019(13) C3 0.027(2) 0.0340(18) 0.030(2) 0.0147(15) -0.0009(16) -0.0022(15) C4 0.0205(18) 0.0231(16) 0.0204(18) 0.0063(13) -0.0001(14) -0.0030(13) C5 0.0230(19) 0.0220(16) 0.0181(18) -0.0019(12) 0.0013(14) -0.0022(13) C6 0.0184(18) 0.0199(15) 0.0200(18) -0.0029(12) 0.0053(14) -0.0001(12) C7 0.0231(19) 0.0267(17) 0.0215(18) -0.0053(14) -0.0017(15) -0.0027(14) C8 0.034(2) 0.0233(17) 0.033(2) -0.0080(14) 0.0051(17) -0.0101(15) C9 0.028(2) 0.0180(15) 0.0250(19) 0.0002(13) 0.0045(15) -0.0046(13) C10 0.0157(17) 0.0191(15) 0.0213(18) -0.0002(13) 0.0057(14) 0.0007(12) C11 0.0226(18) 0.0172(15) 0.0169(17) 0.0032(12) 0.0022(14) -0.0036(13) C12 0.0250(19) 0.0210(15) 0.0200(18) 0.0062(13) 0.0001(14) 0.0049(14) C13 0.0179(18) 0.0246(16) 0.0230(18) 0.0038(13) -0.0068(14) 0.0032(14) C14 0.0209(18) 0.0146(14) 0.0120(16) -0.0030(11) 0.0042(14) 0.0007(12) C15 0.0165(17) 0.0167(14) 0.0185(17) 0.0021(12) -0.0028(13) -0.0026(12) C16 0.0151(17) 0.0241(16) 0.0210(18) -0.0002(13) -0.0011(14) 0.0016(13) C17 0.0175(18) 0.0308(17) 0.0221(18) 0.0064(13) 0.0042(14) -0.0025(13) C18 0.0155(18) 0.0212(16) 0.0279(19) 0.0038(13) -0.0057(15) -0.0011(13) C19 0.0178(18) 0.0228(16) 0.0266(19) -0.0066(13) -0.0033(15) 0.0012(13) C20 0.0149(17) 0.0259(16) 0.0206(18) -0.0010(13) -0.0025(14) 0.0011(13) C21 0.032(2) 0.0287(17) 0.0294(19) 0.0001(14) 0.0108(16) 0.0038(15) C22 0.026(2) 0.0272(17) 0.043(2) 0.0053(15) 0.0003(17) -0.0066(15) C23 0.039(2) 0.0304(18) 0.028(2) -0.0055(15) 0.0117(17) -0.0058(16) C24 0.0174(18) 0.0287(18) 0.0138(17) 0.0049(13) -0.0028(13) 0.0020(14) _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 C24 1.828(3) . ? Ru1 H1 1.94(3) . ? Ru1 C14 2.002(3) . ? Ru1 N2 2.135(2) . ? Ru1 N1 2.262(2) . ? Ru1 Br1 2.6686(4) . ? O1 C24 1.157(3) . ? N1 C5 1.488(3) . ? N1 C2 1.495(4) . ? N1 C4 1.497(3) . ? N2 C10 1.351(3) . ? N2 C6 1.354(4) . ? N3 C14 1.363(3) . ? N3 C12 1.386(4) . ? N3 C11 1.464(4) . ? N4 C14 1.362(4) . ? N4 C13 1.396(4) . ? N4 C15 1.433(3) . ? C1 C2 1.518(4) . ? C3 C4 1.526(4) . ? C5 C6 1.497(4) . ? C6 C7 1.379(4) . ? C7 C8 1.384(4) . ? C8 C9 1.376(4) . ? C9 C10 1.386(4) . ? C10 C11 1.493(4) . ? C12 C13 1.341(4) . ? C15 C16 1.391(4) . ? C15 C20 1.397(4) . ? C16 C17 1.397(4) . ? C16 C21 1.504(4) . ? C17 C18 1.387(4) . ? C18 C19 1.382(4) . ? C18 C22 1.509(4) . ? C19 C20 1.391(4) . ? C20 C23 1.509(4) . ? 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 C24 Ru1 H1 87.6(7) . . ? C24 Ru1 C14 97.63(12) . . ? H1 Ru1 C14 88.7(8) . . ? C24 Ru1 N2 172.03(11) . . ? H1 Ru1 N2 88.5(7) . . ? C14 Ru1 N2 89.26(10) . . ? C24 Ru1 N1 94.63(10) . . ? H1 Ru1 N1 85.2(8) . . ? C14 Ru1 N1 166.10(9) . . ? N2 Ru1 N1 78.09(8) . . ? C24 Ru1 Br1 95.02(10) . . ? H1 Ru1 Br1 176.4(7) . . ? C14 Ru1 Br1 88.53(8) . . ? N2 Ru1 Br1 89.13(6) . . ? N1 Ru1 Br1 96.92(6) . . ? C5 N1 C2 108.7(2) . . ? C5 N1 C4 108.3(2) . . ? C2 N1 C4 111.4(2) . . ? C5 N1 Ru1 101.44(16) . . ? C2 N1 Ru1 114.76(17) . . ? C4 N1 Ru1 111.51(17) . . ? C10 N2 C6 118.9(2) . . ? C10 N2 Ru1 126.86(19) . . ? C6 N2 Ru1 114.23(18) . . ? C14 N3 C12 111.4(2) . . ? C14 N3 C11 125.4(2) . . ? C12 N3 C11 122.6(2) . . ? C14 N4 C13 111.3(2) . . ? C14 N4 C15 125.7(2) . . ? C13 N4 C15 122.5(2) . . ? N1 C2 C1 114.1(2) . . ? N1 C4 C3 116.0(2) . . ? N1 C5 C6 111.9(2) . . ? N2 C6 C7 121.8(3) . . ? N2 C6 C5 115.6(2) . . ? C7 C6 C5 122.4(3) . . ? C6 C7 C8 119.0(3) . . ? C9 C8 C7 119.5(3) . . ? C8 C9 C10 119.2(3) . . ? N2 C10 C9 121.5(3) . . ? N2 C10 C11 117.2(2) . . ? C9 C10 C11 121.1(3) . . ? N3 C11 C10 116.2(2) . . ? C13 C12 N3 107.1(2) . . ? C12 C13 N4 106.5(3) . . ? N4 C14 N3 103.7(2) . . ? N4 C14 Ru1 133.5(2) . . ? N3 C14 Ru1 122.5(2) . . ? C16 C15 C20 122.7(3) . . ? C16 C15 N4 119.3(2) . . ? C20 C15 N4 118.0(3) . . ? C15 C16 C17 117.2(3) . . ? C15 C16 C21 121.3(3) . . ? C17 C16 C21 121.5(3) . . ? C18 C17 C16 121.8(3) . . ? C19 C18 C17 118.8(3) . . ? C19 C18 C22 121.0(3) . . ? C17 C18 C22 120.2(3) . . ? C18 C19 C20 121.9(3) . . ? C19 C20 C15 117.4(3) . . ? C19 C20 C23 121.6(3) . . ? C15 C20 C23 121.0(3) . . ? O1 C24 Ru1 173.6(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.314 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.076 #===>END data_3b _database_code_depnum_ccdc_archive 'CCDC 824077' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52.50 H57 N4 O P Ru' _chemical_formula_weight 892.06 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' P P 0.1023 0.0942 '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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1370(5) _cell_length_b 18.7042(10) _cell_length_c 26.1341(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.801(2) _cell_angle_gamma 90.00 _cell_volume 4443.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 121(2) _cell_measurement_reflns_used 37440 _cell_measurement_theta_min 1.57 _cell_measurement_theta_max 27.52 _exptl_crystal_description plate _exptl_crystal_colour red-orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1868 _exptl_absorpt_coefficient_mu 0.432 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9263 _exptl_absorpt_correction_T_max 0.9581 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 121(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 37440 _diffrn_reflns_av_R_equivalents 0.0730 _diffrn_reflns_av_sigmaI/netI 0.0904 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.52 _reflns_number_total 10188 _reflns_number_gt 7080 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0761P)^2^+15.5604P] 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 10188 _refine_ls_number_parameters 486 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1035 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.1786 _refine_ls_wR_factor_gt 0.1609 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.041 _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 0.27336(4) 0.682487(19) 0.169234(14) 0.01370(11) Uani 1 1 d . . . H1 H 0.408(6) 0.668(3) 0.1333(19) 0.019(13) Uiso 1 1 d . . . P1 P 0.06550(13) 0.71009(6) 0.22113(5) 0.0148(3) Uani 1 1 d . . . O1 O 0.0927(4) 0.59453(19) 0.09057(13) 0.0286(9) Uani 1 1 d . . . N1 N 0.3750(4) 0.5877(2) 0.21611(16) 0.0187(9) Uani 1 1 d . . . N2 N 0.4276(4) 0.7342(2) 0.22300(14) 0.0146(8) Uani 1 1 d . . . N3 N 0.3032(4) 0.8393(2) 0.14965(15) 0.0151(8) Uani 1 1 d . . . N4 N 0.2213(5) 0.7900(2) 0.07794(15) 0.0201(9) Uani 1 1 d . . . C1 C 0.2578(6) 0.4749(3) 0.1762(2) 0.0297(13) Uani 1 1 d . . . H1A H 0.2802 0.4326 0.1563 0.045 Uiso 1 1 calc R . . H1B H 0.1793 0.5025 0.1570 0.045 Uiso 1 1 calc R . . H1C H 0.2258 0.4599 0.2093 0.045 Uiso 1 1 calc R . . C2 C 0.3942(6) 0.5209(3) 0.1857(2) 0.0240(11) Uani 1 1 d . . . H2A H 0.4736 0.4919 0.2041 0.029 Uiso 1 1 calc R . . H2B H 0.4268 0.5346 0.1520 0.029 Uiso 1 1 calc R . . C3 C 0.3892(6) 0.5192(3) 0.3014(2) 0.0309(13) Uani 1 1 d . . . H3A H 0.3338 0.5119 0.3312 0.046 Uiso 1 1 calc R . . H3B H 0.4860 0.5394 0.3129 0.046 Uiso 1 1 calc R . . H3C H 0.4018 0.4733 0.2843 0.046 Uiso 1 1 calc R . . C4 C 0.3059(6) 0.5702(3) 0.26405(19) 0.0228(11) Uani 1 1 d . . . H4A H 0.2074 0.5497 0.2539 0.027 Uiso 1 1 calc R . . H4B H 0.2911 0.6155 0.2825 0.027 Uiso 1 1 calc R . . C5 C 0.5261(5) 0.6164(2) 0.2299(2) 0.0204(10) Uani 1 1 d . . . H5A H 0.5796 0.6176 0.1988 0.024 Uiso 1 1 calc R . . H5B H 0.5804 0.5843 0.2553 0.024 Uiso 1 1 calc R . . C6 C 0.5207(5) 0.6900(3) 0.25194(18) 0.0182(10) Uani 1 1 d . . . C7 C 0.6007(6) 0.7107(3) 0.29633(19) 0.0226(11) Uani 1 1 d . . . H7A H 0.6627 0.6777 0.3159 0.027 Uiso 1 1 calc R . . C8 C 0.5890(6) 0.7826(3) 0.31259(19) 0.0216(11) Uani 1 1 d . . . H8A H 0.6390 0.7980 0.3443 0.026 Uiso 1 1 calc R . . C9 C 0.5057(5) 0.8294(3) 0.28233(18) 0.0193(10) Uani 1 1 d . . . H9A H 0.4992 0.8779 0.2928 0.023 Uiso 1 1 calc R . . C10 C 0.4270(5) 0.8064(3) 0.23442(18) 0.0169(10) Uani 1 1 d . . . C11 C 0.3551(5) 0.8547(3) 0.20162(18) 0.0175(10) Uani 1 1 d . . . H11A H 0.3388 0.9013 0.2143 0.021 Uiso 1 1 calc R . . C12 C 0.2957(6) 0.8920(3) 0.11208(19) 0.0225(11) Uani 1 1 d . . . H12A H 0.3223 0.9408 0.1170 0.027 Uiso 1 1 calc R . . C13 C 0.2443(7) 0.8615(3) 0.0676(2) 0.0293(12) Uani 1 1 d . . . H13A H 0.2268 0.8844 0.0352 0.035 Uiso 1 1 calc R . . C14 C 0.2553(5) 0.7746(2) 0.12926(17) 0.0154(9) Uani 1 1 d . . . C15 C 0.1798(6) 0.7400(3) 0.03703(17) 0.0190(10) Uani 1 1 d . . . C16 C 0.0309(6) 0.7278(3) 0.02102(19) 0.0242(11) Uani 1 1 d . . . C17 C -0.0041(6) 0.6801(3) -0.0180(2) 0.0287(12) Uani 1 1 d . . . H17A H -0.1048 0.6716 -0.0290 0.034 Uiso 1 1 calc R . . C18 C 0.1036(7) 0.6433(3) -0.04237(19) 0.0285(12) Uani 1 1 d . . . C19 C 0.2500(6) 0.6588(3) -0.0265(2) 0.0286(12) Uani 1 1 d . . . H19A H 0.3247 0.6357 -0.0432 0.034 Uiso 1 1 calc R . . C20 C 0.2909(6) 0.7066(3) 0.01266(18) 0.0237(11) Uani 1 1 d . . . C21 C -0.0869(6) 0.7656(4) 0.0470(2) 0.0369(14) Uani 1 1 d . . . H21A H -0.1838 0.7519 0.0304 0.055 Uiso 1 1 calc R . . H21B H -0.0742 0.8174 0.0440 0.055 Uiso 1 1 calc R . . H21C H -0.0794 0.7521 0.0834 0.055 Uiso 1 1 calc R . . C22 C 0.0612(8) 0.5879(3) -0.0830(2) 0.0391(15) Uani 1 1 d . . . H22A H 0.1476 0.5751 -0.1004 0.059 Uiso 1 1 calc R . . H22B H -0.0154 0.6072 -0.1081 0.059 Uiso 1 1 calc R . . H22C H 0.0239 0.5452 -0.0668 0.059 Uiso 1 1 calc R . . C23 C 0.4497(6) 0.7245(3) 0.0276(2) 0.0318(13) Uani 1 1 d . . . H23A H 0.5106 0.7020 0.0033 0.048 Uiso 1 1 calc R . . H23B H 0.4792 0.7066 0.0624 0.048 Uiso 1 1 calc R . . H23C H 0.4629 0.7764 0.0268 0.048 Uiso 1 1 calc R . . C24 C 0.1586(5) 0.6304(3) 0.12097(18) 0.0185(10) Uani 1 1 d . . . C25 C -0.0360(5) 0.6286(2) 0.23719(18) 0.0166(10) Uani 1 1 d . . . C26 C -0.0521(5) 0.6090(3) 0.28803(19) 0.0204(10) Uani 1 1 d . . . H26A H -0.0214 0.6408 0.3154 0.025 Uiso 1 1 calc R . . C27 C -0.1134(6) 0.5425(3) 0.2986(2) 0.0255(11) Uani 1 1 d . . . H27A H -0.1226 0.5291 0.3332 0.031 Uiso 1 1 calc R . . C28 C -0.1602(6) 0.4966(3) 0.2592(2) 0.0254(12) Uani 1 1 d . . . H28A H -0.1993 0.4510 0.2665 0.031 Uiso 1 1 calc R . . C29 C -0.1496(6) 0.5173(3) 0.2088(2) 0.0232(11) Uani 1 1 d . . . H29A H -0.1858 0.4865 0.1815 0.028 Uiso 1 1 calc R . . C30 C -0.0872(5) 0.5821(3) 0.19763(19) 0.0184(10) Uani 1 1 d . . . H30A H -0.0792 0.5951 0.1629 0.022 Uiso 1 1 calc R . . C31 C -0.0785(5) 0.7660(2) 0.18754(17) 0.0159(9) Uani 1 1 d . . . C32 C -0.2219(5) 0.7435(3) 0.17305(18) 0.0191(10) Uani 1 1 d . . . H32A H -0.2493 0.6958 0.1802 0.023 Uiso 1 1 calc R . . C33 C -0.3258(6) 0.7893(3) 0.14838(19) 0.0210(10) Uani 1 1 d . . . H33A H -0.4233 0.7732 0.1388 0.025 Uiso 1 1 calc R . . C34 C -0.2857(6) 0.8588(3) 0.1378(2) 0.0228(11) Uani 1 1 d . . . H34A H -0.3562 0.8905 0.1210 0.027 Uiso 1 1 calc R . . C35 C -0.1435(6) 0.8823(3) 0.15174(19) 0.0226(11) Uani 1 1 d . . . H35A H -0.1168 0.9300 0.1442 0.027 Uiso 1 1 calc R . . C36 C -0.0402(5) 0.8368(2) 0.17651(19) 0.0184(10) Uani 1 1 d . . . H36A H 0.0570 0.8534 0.1861 0.022 Uiso 1 1 calc R . . C37 C 0.0849(5) 0.7555(3) 0.28434(18) 0.0192(10) Uani 1 1 d . . . C38 C 0.2131(6) 0.7484(3) 0.31756(19) 0.0214(11) Uani 1 1 d . . . H38A H 0.2948 0.7237 0.3062 0.026 Uiso 1 1 calc R . . C39 C 0.2239(6) 0.7765(3) 0.36681(19) 0.0244(11) Uani 1 1 d . . . H39A H 0.3117 0.7702 0.3891 0.029 Uiso 1 1 calc R . . C40 C 0.1077(6) 0.8137(3) 0.3835(2) 0.0284(12) Uani 1 1 d . . . H40A H 0.1150 0.8331 0.4172 0.034 Uiso 1 1 calc R . . C41 C -0.0200(6) 0.8224(3) 0.3507(2) 0.0289(12) Uani 1 1 d . . . H41A H -0.0998 0.8487 0.3619 0.035 Uiso 1 1 calc R . . C42 C -0.0324(6) 0.7932(3) 0.30195(19) 0.0243(11) Uani 1 1 d . . . H42A H -0.1214 0.7988 0.2802 0.029 Uiso 1 1 calc R . . C1S C -0.0527(15) 0.9080(10) -0.0662(9) 0.240(11) Uiso 1 1 d D . . H1SA H -0.1010 0.9547 -0.0707 0.361 Uiso 1 1 calc R . . H1SB H -0.0749 0.8868 -0.0336 0.361 Uiso 1 1 calc R . . H1SC H -0.0888 0.8764 -0.0947 0.361 Uiso 1 1 calc R . . C2S C 0.1109(6) 0.9173(4) -0.0658(3) 0.113(4) Uiso 1 1 d G . . C3S C 0.1915(8) 0.9791(3) -0.0539(3) 0.089(3) Uiso 1 1 d GD . . H3SA H 0.1423 1.0224 -0.0473 0.107 Uiso 1 1 calc R . . C4S C 0.3441(8) 0.9777(3) -0.0516(3) 0.091(3) Uiso 1 1 d G . . H4SA H 0.3992 1.0200 -0.0434 0.109 Uiso 1 1 calc R . . C5S C 0.4161(6) 0.9144(4) -0.0612(3) 0.114(4) Uiso 1 1 d G . . H5SA H 0.5204 0.9134 -0.0596 0.137 Uiso 1 1 calc R . . C6S C 0.3355(8) 0.8525(3) -0.0731(3) 0.090(3) Uiso 1 1 d G . . H6SA H 0.3847 0.8092 -0.0797 0.108 Uiso 1 1 calc R . . C7S C 0.1829(8) 0.8540(3) -0.0755(3) 0.092(3) Uiso 1 1 d GD . . H7SA H 0.1278 0.8117 -0.0836 0.111 Uiso 1 1 calc R . . C8S C 0.588(2) 0.5513(11) 0.0551(8) 0.080(5) Uiso 0.50 1 d P . . C9S C 0.4515(12) 0.5210(5) 0.0387(4) 0.080(3) Uiso 1 1 d . . . C10S C 0.440(2) 0.4853(12) -0.0040(9) 0.090(6) Uiso 0.50 1 d P . . C11S C 0.2931(15) 0.4483(7) -0.0269(5) 0.117(4) Uiso 1 1 d . . . C12S C 0.306(2) 0.4834(10) 0.0144(7) 0.066(4) Uiso 0.50 1 d P . . 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 0.01497(19) 0.01192(18) 0.01438(19) -0.00064(15) 0.00225(13) -0.00056(16) P1 0.0158(6) 0.0136(5) 0.0151(6) -0.0004(5) 0.0022(5) -0.0010(5) O1 0.040(2) 0.0251(19) 0.0203(19) -0.0031(16) 0.0012(16) -0.0119(17) N1 0.017(2) 0.0142(19) 0.025(2) 0.0009(16) 0.0046(17) 0.0021(16) N2 0.015(2) 0.0130(18) 0.0157(19) -0.0010(15) 0.0019(15) 0.0007(15) N3 0.018(2) 0.0112(18) 0.017(2) 0.0010(15) 0.0033(16) 0.0010(15) N4 0.023(2) 0.020(2) 0.018(2) -0.0013(17) 0.0023(17) -0.0014(17) C1 0.033(3) 0.015(2) 0.041(3) -0.002(2) 0.000(3) 0.000(2) C2 0.023(3) 0.015(2) 0.033(3) -0.003(2) 0.002(2) 0.004(2) C3 0.033(3) 0.024(3) 0.034(3) 0.012(2) -0.003(2) -0.002(2) C4 0.022(3) 0.021(2) 0.025(3) 0.002(2) 0.002(2) -0.002(2) C5 0.018(3) 0.015(2) 0.029(3) 0.001(2) 0.002(2) 0.0021(19) C6 0.014(2) 0.018(2) 0.022(2) 0.001(2) 0.0032(18) -0.0006(19) C7 0.017(3) 0.025(3) 0.025(3) 0.003(2) -0.001(2) 0.002(2) C8 0.021(3) 0.029(3) 0.015(2) 0.001(2) -0.0024(19) -0.002(2) C9 0.019(2) 0.018(2) 0.021(2) -0.0029(19) 0.0023(19) -0.0043(19) C10 0.013(2) 0.021(2) 0.017(2) -0.0001(19) 0.0046(18) -0.0013(18) C11 0.021(3) 0.016(2) 0.015(2) -0.0054(18) -0.0011(19) 0.0005(19) C12 0.032(3) 0.016(2) 0.020(3) 0.004(2) 0.003(2) -0.002(2) C13 0.043(4) 0.020(3) 0.025(3) 0.008(2) 0.006(2) 0.003(2) C14 0.015(2) 0.018(2) 0.014(2) -0.0022(18) 0.0037(18) 0.0009(18) C15 0.031(3) 0.016(2) 0.010(2) -0.0001(18) -0.0002(19) 0.000(2) C16 0.031(3) 0.026(3) 0.015(2) 0.003(2) 0.002(2) 0.000(2) C17 0.031(3) 0.032(3) 0.022(3) 0.000(2) -0.004(2) -0.003(3) C18 0.044(4) 0.028(3) 0.012(2) -0.001(2) -0.002(2) -0.001(3) C19 0.036(3) 0.026(3) 0.025(3) -0.002(2) 0.009(2) -0.001(2) C20 0.025(3) 0.033(3) 0.013(2) 0.001(2) 0.002(2) 0.001(2) C21 0.026(3) 0.054(4) 0.030(3) -0.006(3) -0.003(2) 0.007(3) C22 0.059(4) 0.030(3) 0.026(3) -0.009(3) -0.004(3) -0.005(3) C23 0.027(3) 0.044(3) 0.026(3) -0.006(3) 0.010(2) -0.005(3) C24 0.020(3) 0.018(2) 0.019(2) -0.002(2) 0.008(2) -0.001(2) C25 0.012(2) 0.017(2) 0.021(2) 0.0010(19) 0.0046(18) 0.0014(18) C26 0.023(3) 0.018(2) 0.020(2) 0.002(2) 0.004(2) 0.003(2) C27 0.027(3) 0.023(3) 0.028(3) 0.009(2) 0.008(2) 0.005(2) C28 0.023(3) 0.016(2) 0.039(3) 0.004(2) 0.013(2) -0.002(2) C29 0.023(3) 0.015(2) 0.033(3) -0.007(2) 0.007(2) -0.001(2) C30 0.016(2) 0.019(2) 0.020(2) 0.0032(19) 0.0038(19) 0.0024(19) C31 0.021(3) 0.013(2) 0.013(2) -0.0022(18) 0.0009(18) 0.0026(19) C32 0.019(2) 0.019(2) 0.020(2) 0.000(2) 0.0045(19) -0.003(2) C33 0.017(3) 0.025(3) 0.022(3) 0.000(2) 0.001(2) 0.001(2) C34 0.021(3) 0.024(3) 0.023(3) 0.002(2) -0.001(2) 0.008(2) C35 0.027(3) 0.016(2) 0.026(3) -0.001(2) 0.004(2) 0.002(2) C36 0.016(2) 0.016(2) 0.023(3) -0.0041(19) 0.0021(19) 0.0006(18) C37 0.021(3) 0.020(2) 0.017(2) -0.0004(19) 0.0052(19) -0.004(2) C38 0.024(3) 0.019(2) 0.022(3) -0.0003(19) 0.003(2) -0.006(2) C39 0.026(3) 0.027(3) 0.019(3) 0.001(2) 0.001(2) -0.008(2) C40 0.031(3) 0.036(3) 0.018(2) -0.011(2) 0.004(2) -0.011(3) C41 0.030(3) 0.033(3) 0.026(3) -0.008(2) 0.014(2) 0.001(2) C42 0.022(3) 0.030(3) 0.021(3) -0.004(2) 0.001(2) -0.001(2) _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 H1 1.65(5) . ? Ru1 C24 1.836(5) . ? Ru1 C14 2.013(5) . ? Ru1 N2 2.120(4) . ? Ru1 N1 2.298(4) . ? Ru1 P1 2.4968(13) . ? P1 C31 1.834(5) . ? P1 C37 1.850(5) . ? P1 C25 1.855(5) . ? O1 C24 1.161(6) . ? N1 C5 1.491(6) . ? N1 C4 1.494(6) . ? N1 C2 1.500(6) . ? N2 C6 1.359(6) . ? N2 C10 1.383(6) . ? N3 C14 1.377(6) . ? N3 C12 1.388(6) . ? N3 C11 1.422(6) . ? N4 C14 1.376(6) . ? N4 C13 1.384(7) . ? N4 C15 1.441(6) . ? C1 C2 1.514(7) . ? C3 C4 1.515(7) . ? C5 C6 1.497(7) . ? C6 C7 1.363(7) . ? C7 C8 1.419(7) . ? C8 C9 1.360(7) . ? C9 C10 1.445(7) . ? C10 C11 1.367(7) . ? C12 C13 1.337(8) . ? C15 C20 1.399(7) . ? C15 C16 1.401(7) . ? C16 C17 1.367(7) . ? C16 C21 1.506(8) . ? C17 C18 1.406(8) . ? C18 C19 1.391(8) . ? C18 C22 1.506(7) . ? C19 C20 1.382(7) . ? C20 C23 1.501(8) . ? C25 C30 1.394(7) . ? C25 C26 1.400(7) . ? C26 C27 1.403(7) . ? C27 C28 1.375(8) . ? C28 C29 1.386(7) . ? C29 C30 1.383(7) . ? C31 C32 1.392(7) . ? C31 C36 1.407(6) . ? C32 C33 1.388(7) . ? C33 C34 1.385(7) . ? C34 C35 1.386(7) . ? C35 C36 1.382(7) . ? C37 C38 1.392(7) . ? C37 C42 1.400(7) . ? C38 C39 1.385(7) . ? C39 C40 1.376(8) . ? C40 C41 1.386(8) . ? C41 C42 1.381(7) . ? C1S C2S 1.503(13) . ? C2S C3S 1.3900 . ? C2S C7S 1.3900 . ? C3S C4S 1.3900 . ? C4S C5S 1.3900 . ? C5S C6S 1.3900 . ? C6S C7S 1.3900 . ? C8S C11S 1.38(2) 3_665 ? C8S C9S 1.39(2) . ? C8S C10S 1.50(3) 3_665 ? C9S C10S 1.30(2) . ? C9S C10S 1.42(2) 3_665 ? C9S C12S 1.58(2) . ? C10S C10S 1.23(4) 3_665 ? C10S C12S 1.36(3) . ? C10S C9S 1.42(2) 3_665 ? C10S C8S 1.50(3) 3_665 ? C10S C11S 1.57(2) . ? C11S C12S 1.26(2) . ? C11S C8S 1.38(2) 3_665 ? 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 H1 Ru1 C24 85.9(18) . . ? H1 Ru1 C14 82.8(17) . . ? C24 Ru1 C14 94.9(2) . . ? H1 Ru1 N2 88.2(18) . . ? C24 Ru1 N2 172.91(18) . . ? C14 Ru1 N2 88.16(17) . . ? H1 Ru1 N1 83.6(17) . . ? C24 Ru1 N1 97.41(18) . . ? C14 Ru1 N1 160.91(17) . . ? N2 Ru1 N1 78.05(14) . . ? H1 Ru1 P1 177.2(18) . . ? C24 Ru1 P1 94.00(15) . . ? C14 Ru1 P1 94.47(13) . . ? N2 Ru1 P1 92.11(11) . . ? N1 Ru1 P1 99.12(10) . . ? C31 P1 C37 99.5(2) . . ? C31 P1 C25 103.1(2) . . ? C37 P1 C25 100.4(2) . . ? C31 P1 Ru1 113.97(15) . . ? C37 P1 Ru1 124.77(16) . . ? C25 P1 Ru1 112.21(15) . . ? C5 N1 C4 109.6(4) . . ? C5 N1 C2 105.8(4) . . ? C4 N1 C2 110.2(4) . . ? C5 N1 Ru1 99.5(3) . . ? C4 N1 Ru1 115.7(3) . . ? C2 N1 Ru1 115.0(3) . . ? C6 N2 C10 119.2(4) . . ? C6 N2 Ru1 115.4(3) . . ? C10 N2 Ru1 124.9(3) . . ? C14 N3 C12 111.1(4) . . ? C14 N3 C11 127.6(4) . . ? C12 N3 C11 121.4(4) . . ? C14 N4 C13 111.6(4) . . ? C14 N4 C15 127.1(4) . . ? C13 N4 C15 121.0(4) . . ? N1 C2 C1 114.9(4) . . ? N1 C4 C3 116.8(4) . . ? N1 C5 C6 111.0(4) . . ? N2 C6 C7 123.6(4) . . ? N2 C6 C5 112.8(4) . . ? C7 C6 C5 123.6(4) . . ? C6 C7 C8 118.3(5) . . ? C9 C8 C7 119.4(5) . . ? C8 C9 C10 120.8(4) . . ? C11 C10 N2 121.5(4) . . ? C11 C10 C9 120.8(4) . . ? N2 C10 C9 117.8(4) . . ? C10 C11 N3 123.9(4) . . ? C13 C12 N3 107.4(4) . . ? C12 C13 N4 106.9(5) . . ? N4 C14 N3 103.0(4) . . ? N4 C14 Ru1 133.1(3) . . ? N3 C14 Ru1 123.1(3) . . ? C20 C15 C16 121.2(5) . . ? C20 C15 N4 118.6(5) . . ? C16 C15 N4 120.2(4) . . ? C17 C16 C15 118.5(5) . . ? C17 C16 C21 121.2(5) . . ? C15 C16 C21 120.4(5) . . ? C16 C17 C18 122.4(5) . . ? C19 C18 C17 117.3(5) . . ? C19 C18 C22 121.7(5) . . ? C17 C18 C22 121.0(5) . . ? C20 C19 C18 122.4(5) . . ? C19 C20 C15 118.1(5) . . ? C19 C20 C23 121.2(5) . . ? C15 C20 C23 120.6(5) . . ? O1 C24 Ru1 175.9(4) . . ? C30 C25 C26 118.8(4) . . ? C30 C25 P1 118.8(4) . . ? C26 C25 P1 122.2(4) . . ? C25 C26 C27 120.0(5) . . ? C28 C27 C26 120.5(5) . . ? C27 C28 C29 119.3(5) . . ? C30 C29 C28 121.0(5) . . ? C29 C30 C25 120.3(5) . . ? C32 C31 C36 118.5(4) . . ? C32 C31 P1 124.6(4) . . ? C36 C31 P1 117.0(4) . . ? C33 C32 C31 121.3(5) . . ? C34 C33 C32 119.3(5) . . ? C33 C34 C35 120.4(5) . . ? C36 C35 C34 120.3(5) . . ? C35 C36 C31 120.2(5) . . ? C38 C37 C42 117.9(5) . . ? C38 C37 P1 120.8(4) . . ? C42 C37 P1 121.2(4) . . ? C39 C38 C37 121.3(5) . . ? C40 C39 C38 120.1(5) . . ? C39 C40 C41 119.5(5) . . ? C42 C41 C40 120.6(5) . . ? C41 C42 C37 120.6(5) . . ? C3S C2S C7S 120.0 . . ? C3S C2S C1S 127.0(8) . . ? C7S C2S C1S 112.9(8) . . ? C4S C3S C2S 120.0 . . ? C5S C4S C3S 120.0 . . ? C4S C5S C6S 120.0 . . ? C7S C6S C5S 120.0 . . ? C6S C7S C2S 120.0 . . ? C11S C8S C9S 124.5(17) 3_665 . ? C11S C8S C10S 66.1(13) 3_665 3_665 ? C9S C8S C10S 58.5(12) . 3_665 ? C10S C9S C8S 117.9(15) . . ? C10S C9S C10S 53.7(16) . 3_665 ? C8S C9S C10S 64.5(12) . 3_665 ? C10S C9S C12S 55.3(11) . . ? C8S C9S C12S 173.2(14) . . ? C10S C9S C12S 108.8(14) 3_665 . ? C10S C10S C9S 68(2) 3_665 . ? C10S C10S C12S 141(3) 3_665 . ? C9S C10S C12S 73.0(16) . . ? C10S C10S C9S 58.1(18) 3_665 3_665 ? C9S C10S C9S 126.3(16) . 3_665 ? C12S C10S C9S 160(2) . 3_665 ? C10S C10S C8S 115(3) 3_665 3_665 ? C9S C10S C8S 174(2) . 3_665 ? C12S C10S C8S 103.2(17) . 3_665 ? C9S C10S C8S 57.1(13) 3_665 3_665 ? C10S C10S C11S 167(3) 3_665 . ? C9S C10S C11S 123.2(18) . . ? C12S C10S C11S 50.2(11) . . ? C9S C10S C11S 110.3(17) 3_665 . ? C8S C10S C11S 53.2(12) 3_665 . ? C12S C11S C8S 116.5(16) . 3_665 ? C12S C11S C10S 56.0(13) . . ? C8S C11S C10S 60.7(13) 3_665 . ? C11S C12S C10S 73.8(14) . . ? C11S C12S C9S 125.5(15) . . ? C10S C12S C9S 51.7(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.099 _refine_diff_density_min -0.758 _refine_diff_density_rms 0.133