# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ch740a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H43 N2 O5 P Ru + (solvent)' _chemical_formula_sum 'C24 H43 N2 O5 P Ru' _chemical_formula_weight 571.64 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)/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 17.9131(16) _cell_length_b 10.7282(10) _cell_length_c 15.6284(14) _cell_angle_alpha 90.00 _cell_angle_beta 112.6070(10) _cell_angle_gamma 90.00 _cell_volume 2772.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 1989 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 28.32 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.657 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8477 _exptl_absorpt_correction_T_max 0.8530 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2008/1) Bruker AXS area detector absorption and other corrections, University of Gottingen, Germany 2008. ; _exptl_special_details ; 3000 frames x 10 sec @ 5.070 cm; 0.5 deg omega scans; 0.45 deg phi; 50kV/30mA ; _diffrn_ambient_temperature 85(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-I CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 73076 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 28.34 _reflns_number_total 6912 _reflns_number_gt 6449 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX-I' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; The structure contains a region of electron density due to disordered lattice solvent. The SQUEEZE subroutine of the PLATON program suite indicated the presence of two solvent accessible voids in the structure. Located at inversion centers (1, 0, 1/2), (0, 1/2, 0) the voids have a total volume of 535.1 A^3. PLATON estimated a total contribution of 105 electrons per cell due to diffuse solvent scattering. This corresponds closely to the presence of 4 molecules of methyl formate per unit cell. These have been included in all of the derived crystal quantities (FW, density, F(000), etc). 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^)+(0.0265P)^2^+1.3417P] 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 6912 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0233 _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0560 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 P1 P 0.194070(19) 0.83451(3) 0.26048(2) 0.01272(7) Uani 1 1 d . . . Ru1 Ru 0.233099(5) 0.674171(9) 0.360892(6) 0.01119(4) Uani 1 1 d . . . H1 H 0.1635(11) 0.6073(18) 0.2855(13) 0.035(5) Uiso 1 1 d . . . O1 O 0.10770(6) 0.72116(12) 0.43985(7) 0.0289(2) Uani 1 1 d . . . O2 O 0.34772(5) 0.73832(8) 0.46802(6) 0.01460(17) Uani 1 1 d . . . O3 O 0.47462(6) 0.69744(9) 0.46410(7) 0.01805(18) Uani 1 1 d . . . N1 N 0.29743(6) 0.50042(10) 0.42863(7) 0.01349(19) Uani 1 1 d . . . N2 N 0.30506(6) 0.63726(10) 0.28599(7) 0.01260(19) Uani 1 1 d . . . C1 C 0.15956(8) 0.70365(13) 0.41378(9) 0.0181(2) Uani 1 1 d . . . C2 C 0.40743(7) 0.65467(12) 0.48587(8) 0.0147(2) Uani 1 1 d . . . H2A H 0.4280 0.6324 0.5531 0.018 Uiso 1 1 calc R . . C3 C 0.37885(7) 0.53249(11) 0.42729(8) 0.0130(2) Uani 1 1 d . . . H3A H 0.4184 0.4632 0.4535 0.016 Uiso 1 1 calc R . . C4 C 0.36841(7) 0.56171(11) 0.32897(8) 0.0135(2) Uani 1 1 d . . . C5 C 0.41964(8) 0.52592(12) 0.28575(9) 0.0173(2) Uani 1 1 d . . . H5A H 0.4633 0.4704 0.3153 0.021 Uiso 1 1 calc R . . C6 C 0.40545(8) 0.57348(13) 0.19783(9) 0.0193(3) Uani 1 1 d . . . H6A H 0.4396 0.5498 0.1668 0.023 Uiso 1 1 calc R . . C7 C 0.34155(8) 0.65555(12) 0.15516(9) 0.0171(2) Uani 1 1 d . . . H7A H 0.3326 0.6900 0.0960 0.021 Uiso 1 1 calc R . . C8 C 0.29126(8) 0.68570(11) 0.20134(8) 0.0142(2) Uani 1 1 d . . . C9 C 0.21932(8) 0.77146(12) 0.16389(8) 0.0151(2) Uani 1 1 d . . . H9A H 0.1723 0.7253 0.1201 0.018 Uiso 1 1 calc R . . H9B H 0.2316 0.8411 0.1298 0.018 Uiso 1 1 calc R . . C10 C 0.51238(8) 0.80257(14) 0.51886(11) 0.0240(3) Uani 1 1 d . . . H10A H 0.4721 0.8682 0.5103 0.036 Uiso 1 1 calc R . . H10B H 0.5550 0.8337 0.4997 0.036 Uiso 1 1 calc R . . H10C H 0.5361 0.7784 0.5843 0.036 Uiso 1 1 calc R . . C11 C 0.30222(8) 0.48336(12) 0.52578(8) 0.0158(2) Uani 1 1 d . . . H11A H 0.2467 0.4712 0.5236 0.019 Uiso 1 1 calc R . . H11B H 0.3235 0.5612 0.5607 0.019 Uiso 1 1 calc R . . C12 C 0.35469(8) 0.37451(13) 0.57955(9) 0.0201(3) Uani 1 1 d . . . H12A H 0.3295 0.2956 0.5515 0.030 Uiso 1 1 calc R . . H12B H 0.3596 0.3775 0.6442 0.030 Uiso 1 1 calc R . . H12C H 0.4085 0.3808 0.5774 0.030 Uiso 1 1 calc R . . C13 C 0.26590(7) 0.38524(12) 0.37291(9) 0.0160(2) Uani 1 1 d . . . H13A H 0.3054 0.3169 0.3985 0.019 Uiso 1 1 calc R . . H13B H 0.2605 0.4003 0.3083 0.019 Uiso 1 1 calc R . . C14 C 0.18416(8) 0.34477(13) 0.37259(10) 0.0206(3) Uani 1 1 d . . . H14A H 0.1917 0.3083 0.4328 0.031 Uiso 1 1 calc R . . H14B H 0.1599 0.2827 0.3237 0.031 Uiso 1 1 calc R . . H14C H 0.1484 0.4173 0.3610 0.031 Uiso 1 1 calc R . . C15 C 0.08427(8) 0.87904(13) 0.20190(9) 0.0184(2) Uani 1 1 d . . . C16 C 0.03371(8) 0.75856(14) 0.18371(10) 0.0234(3) Uani 1 1 d . . . H16A H 0.0407 0.7193 0.2429 0.035 Uiso 1 1 calc R . . H16B H 0.0518 0.7010 0.1468 0.035 Uiso 1 1 calc R . . H16C H -0.0235 0.7787 0.1498 0.035 Uiso 1 1 calc R . . C17 C 0.06331(9) 0.94416(14) 0.10752(9) 0.0238(3) Uani 1 1 d . . . H17A H 0.0054 0.9637 0.0808 0.036 Uiso 1 1 calc R . . H17B H 0.0766 0.8888 0.0655 0.036 Uiso 1 1 calc R . . H17C H 0.0946 1.0214 0.1163 0.036 Uiso 1 1 calc R . . C18 C 0.05952(9) 0.96290(14) 0.26640(10) 0.0232(3) Uani 1 1 d . . . H18A H 0.0009 0.9758 0.2395 0.035 Uiso 1 1 calc R . . H18B H 0.0870 1.0435 0.2737 0.035 Uiso 1 1 calc R . . H18C H 0.0749 0.9228 0.3271 0.035 Uiso 1 1 calc R . . C19 C 0.25919(8) 0.97823(12) 0.29890(9) 0.0170(2) Uani 1 1 d . . . C20 C 0.23275(9) 1.09050(13) 0.23286(9) 0.0214(3) Uani 1 1 d . . . H20A H 0.1796 1.1196 0.2288 0.032 Uiso 1 1 calc R . . H20B H 0.2294 1.0656 0.1712 0.032 Uiso 1 1 calc R . . H20C H 0.2723 1.1579 0.2565 0.032 Uiso 1 1 calc R . . C21 C 0.26271(9) 1.01453(13) 0.39580(9) 0.0209(3) Uani 1 1 d . . . H21A H 0.2987 1.0863 0.4189 0.031 Uiso 1 1 calc R . . H21B H 0.2833 0.9440 0.4383 0.031 Uiso 1 1 calc R . . H21C H 0.2083 1.0363 0.3918 0.031 Uiso 1 1 calc R . . C22 C 0.34553(8) 0.94183(12) 0.30900(9) 0.0194(3) Uani 1 1 d . . . H22A H 0.3457 0.9226 0.2478 0.029 Uiso 1 1 calc R . . H22B H 0.3632 0.8684 0.3491 0.029 Uiso 1 1 calc R . . H22C H 0.3825 1.0114 0.3365 0.029 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 P1 0.01315(14) 0.01400(15) 0.01061(13) 0.00103(11) 0.00414(11) 0.00228(11) Ru1 0.01027(5) 0.01361(6) 0.00971(5) 0.00100(3) 0.00385(4) 0.00167(3) O1 0.0202(5) 0.0493(7) 0.0214(5) 0.0097(5) 0.0127(4) 0.0126(5) O2 0.0125(4) 0.0167(4) 0.0133(4) -0.0019(3) 0.0034(3) 0.0018(3) O3 0.0140(4) 0.0193(4) 0.0213(4) -0.0039(4) 0.0073(4) -0.0021(3) N1 0.0125(5) 0.0163(5) 0.0125(4) 0.0010(4) 0.0058(4) 0.0007(4) N2 0.0121(5) 0.0140(5) 0.0116(4) -0.0008(4) 0.0044(4) -0.0001(4) C1 0.0164(6) 0.0237(6) 0.0125(5) 0.0044(5) 0.0035(5) 0.0040(5) C2 0.0131(5) 0.0177(6) 0.0128(5) -0.0008(4) 0.0043(4) 0.0004(4) C3 0.0109(5) 0.0158(5) 0.0123(5) 0.0010(4) 0.0043(4) 0.0022(4) C4 0.0129(5) 0.0144(5) 0.0126(5) -0.0007(4) 0.0042(4) -0.0001(4) C5 0.0158(6) 0.0196(6) 0.0175(6) 0.0005(5) 0.0074(5) 0.0033(5) C6 0.0209(6) 0.0231(6) 0.0185(6) -0.0011(5) 0.0126(5) 0.0017(5) C7 0.0209(6) 0.0189(6) 0.0133(5) 0.0002(5) 0.0085(5) -0.0001(5) C8 0.0165(6) 0.0137(5) 0.0122(5) -0.0007(4) 0.0051(5) -0.0005(4) C9 0.0176(6) 0.0161(6) 0.0115(5) 0.0011(4) 0.0055(4) 0.0023(5) C10 0.0167(6) 0.0235(7) 0.0291(7) -0.0059(6) 0.0059(6) -0.0033(5) C11 0.0169(6) 0.0190(6) 0.0135(5) 0.0033(5) 0.0079(4) 0.0036(5) C12 0.0210(6) 0.0226(6) 0.0182(6) 0.0068(5) 0.0091(5) 0.0062(5) C13 0.0150(6) 0.0149(6) 0.0179(6) -0.0008(5) 0.0060(5) -0.0002(4) C14 0.0164(6) 0.0196(6) 0.0262(7) -0.0004(5) 0.0088(5) -0.0015(5) C15 0.0161(6) 0.0223(6) 0.0158(6) 0.0040(5) 0.0050(5) 0.0064(5) C16 0.0135(6) 0.0285(7) 0.0236(6) 0.0028(6) 0.0021(5) 0.0024(5) C17 0.0228(7) 0.0298(7) 0.0163(6) 0.0068(5) 0.0048(5) 0.0100(6) C18 0.0212(6) 0.0282(7) 0.0215(6) 0.0043(5) 0.0094(5) 0.0103(5) C19 0.0213(6) 0.0148(6) 0.0155(5) 0.0004(5) 0.0076(5) 0.0009(5) C20 0.0296(7) 0.0168(6) 0.0203(6) 0.0026(5) 0.0123(5) 0.0024(5) C21 0.0278(7) 0.0181(6) 0.0176(6) -0.0012(5) 0.0095(5) 0.0012(5) C22 0.0188(6) 0.0176(6) 0.0212(6) -0.0013(5) 0.0072(5) -0.0029(5) _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 P1 C9 1.8617(12) . ? P1 C15 1.8843(13) . ? P1 C19 1.8868(13) . ? P1 Ru1 2.2509(3) . ? Ru1 H1 1.526(19) . ? Ru1 C1 1.8319(13) . ? Ru1 N2 2.0854(10) . ? Ru1 O2 2.2022(9) . ? Ru1 N1 2.2328(10) . ? O1 C1 1.1641(17) . ? O2 C2 1.3409(15) . ? O3 C10 1.4201(16) . ? O3 C2 1.4456(15) . ? N1 C13 1.4919(16) . ? N1 C11 1.4987(15) . ? N1 C3 1.5065(15) . ? N2 C4 1.3453(16) . ? N2 C8 1.3528(16) . ? C2 C3 1.5678(17) . ? C3 C4 1.5077(16) . ? C4 C5 1.3864(17) . ? C5 C6 1.3945(18) . ? C6 C7 1.3940(19) . ? C7 C8 1.3917(18) . ? C8 C9 1.5066(17) . ? C11 C12 1.5317(17) . ? C13 C14 1.5253(18) . ? C15 C18 1.5381(19) . ? C15 C16 1.541(2) . ? C15 C17 1.5423(18) . ? C19 C20 1.5377(18) . ? C19 C21 1.5413(18) . ? C19 C22 1.5431(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 C9 P1 C15 103.40(6) . . ? C9 P1 C19 103.99(6) . . ? C15 P1 C19 110.46(6) . . ? C9 P1 Ru1 100.40(4) . . ? C15 P1 Ru1 121.26(4) . . ? C19 P1 Ru1 114.47(4) . . ? H1 Ru1 C1 85.1(7) . . ? H1 Ru1 N2 88.6(7) . . ? C1 Ru1 N2 173.20(5) . . ? H1 Ru1 O2 168.6(7) . . ? C1 Ru1 O2 103.01(5) . . ? N2 Ru1 O2 83.64(4) . . ? H1 Ru1 N1 95.3(7) . . ? C1 Ru1 N1 105.06(5) . . ? N2 Ru1 N1 77.87(4) . . ? O2 Ru1 N1 74.93(4) . . ? H1 Ru1 P1 83.0(7) . . ? C1 Ru1 P1 95.63(4) . . ? N2 Ru1 P1 81.21(3) . . ? O2 Ru1 P1 103.90(3) . . ? N1 Ru1 P1 159.05(3) . . ? C2 O2 Ru1 112.65(7) . . ? C10 O3 C2 110.92(10) . . ? C13 N1 C11 110.58(10) . . ? C13 N1 C3 109.42(9) . . ? C11 N1 C3 111.30(9) . . ? C13 N1 Ru1 113.84(7) . . ? C11 N1 Ru1 113.60(7) . . ? C3 N1 Ru1 97.39(7) . . ? C4 N2 C8 121.45(11) . . ? C4 N2 Ru1 114.77(8) . . ? C8 N2 Ru1 123.78(8) . . ? O1 C1 Ru1 174.14(11) . . ? O2 C2 O3 114.10(10) . . ? O2 C2 C3 112.50(10) . . ? O3 C2 C3 104.04(9) . . ? N1 C3 C4 108.67(9) . . ? N1 C3 C2 106.47(9) . . ? C4 C3 C2 107.82(10) . . ? N2 C4 C5 120.85(11) . . ? N2 C4 C3 112.61(10) . . ? C5 C4 C3 126.36(11) . . ? C4 C5 C6 118.34(12) . . ? C7 C6 C5 120.50(12) . . ? C8 C7 C6 118.36(12) . . ? N2 C8 C7 120.43(11) . . ? N2 C8 C9 114.96(11) . . ? C7 C8 C9 124.61(11) . . ? C8 C9 P1 110.18(8) . . ? N1 C11 C12 115.65(10) . . ? N1 C13 C14 112.66(10) . . ? C18 C15 C16 108.33(11) . . ? C18 C15 C17 109.66(11) . . ? C16 C15 C17 107.09(11) . . ? C18 C15 P1 109.87(9) . . ? C16 C15 P1 107.86(9) . . ? C17 C15 P1 113.86(9) . . ? C20 C19 C21 110.32(11) . . ? C20 C19 C22 107.75(11) . . ? C21 C19 C22 107.61(11) . . ? C20 C19 P1 115.68(9) . . ? C21 C19 P1 107.81(9) . . ? C22 C19 P1 107.37(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.674 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 936845' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ch765b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H43 N2 O2 P Ru, C5 H8 O' _chemical_formula_sum 'C30 H51 N2 O3 P Ru' _chemical_formula_weight 619.77 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)/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 18.7853(6) _cell_length_b 11.0118(3) _cell_length_c 15.0703(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.438(1) _cell_angle_gamma 90.00 _cell_volume 3044.27(15) _cell_formula_units_Z 4 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 9916 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 29.57 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.600 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8695 _exptl_absorpt_correction_T_max 0.8997 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2008/1) Bruker AXS area detector absorption and other corrections, University of Gottingen, Germany 2008. ; _exptl_special_details ; 4095 frames x 20 sec. @ 5.070 cm; 0.5 deg. omega scans; 0.45 deg. phi ; _diffrn_ambient_temperature 85(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 120048 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 29.62 _reflns_number_total 8551 _reflns_number_gt 7780 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART-APEX' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; The cyclopentanone solvate is disordered in two orientations, each at 50% occupancy. SAME restraints were employed in the refinement. 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^)+(0.0396P)^2^+1.4469P] 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 8551 _refine_ls_number_parameters 400 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0660 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.228849(17) 0.16608(2) 0.08028(2) 0.01421(6) Uani 1 1 d . . . Ru1 Ru 0.244410(5) 0.336915(8) 0.164830(6) 0.01342(4) Uani 1 1 d . . . H1 H 0.1773(10) 0.3792(17) 0.0946(12) 0.030(5) Uiso 1 1 d . . . O1 O 0.13953(5) 0.25088(9) 0.27512(6) 0.02339(19) Uani 1 1 d . . . O2 O 0.34834(5) 0.31939(8) 0.26433(6) 0.01754(17) Uani 1 1 d . . . N1 N 0.31019(5) 0.38326(9) 0.07410(7) 0.01455(18) Uani 1 1 d . . . N2 N 0.27816(6) 0.52804(9) 0.20372(7) 0.01683(19) Uani 1 1 d . . . C1 C 0.18188(7) 0.28771(11) 0.23533(8) 0.0173(2) Uani 1 1 d . . . C2 C 0.39637(7) 0.41417(11) 0.26136(8) 0.0169(2) Uani 1 1 d . . . C3 C 0.43309(7) 0.45836(12) 0.35898(8) 0.0222(2) Uani 1 1 d . . . H3A H 0.4568 0.5382 0.3567 0.027 Uiso 1 1 calc R . . H3B H 0.3967 0.4654 0.3974 0.027 Uiso 1 1 calc R . . C4 C 0.49008(8) 0.35977(13) 0.39611(9) 0.0253(3) Uani 1 1 d . . . H4A H 0.4702 0.3005 0.4338 0.030 Uiso 1 1 calc R . . H4B H 0.5347 0.3967 0.4335 0.030 Uiso 1 1 calc R . . C5 C 0.50711(7) 0.29722(13) 0.31110(9) 0.0248(3) Uani 1 1 d . . . H5A H 0.5602 0.2983 0.3133 0.030 Uiso 1 1 calc R . . H5B H 0.4901 0.2119 0.3069 0.030 Uiso 1 1 calc R . . C6 C 0.46583(7) 0.37121(12) 0.23022(9) 0.0197(2) Uani 1 1 d . . . H6A H 0.4530 0.3203 0.1749 0.024 Uiso 1 1 calc R . . H6B H 0.4952 0.4413 0.2177 0.024 Uiso 1 1 calc R . . C7 C 0.35670(7) 0.51743(11) 0.19603(8) 0.0165(2) Uani 1 1 d . . . H7A H 0.3826 0.5968 0.2096 0.020 Uiso 1 1 calc R . . C8 C 0.35550(6) 0.47748(10) 0.09999(8) 0.0158(2) Uani 1 1 d . . . C9 C 0.39922(7) 0.52107(11) 0.04369(8) 0.0188(2) Uani 1 1 d . . . H9A H 0.4296 0.5898 0.0607 0.023 Uiso 1 1 calc R . . C10 C 0.39751(7) 0.46168(12) -0.03838(8) 0.0199(2) Uani 1 1 d . . . H10A H 0.4267 0.4905 -0.0782 0.024 Uiso 1 1 calc R . . C11 C 0.35325(7) 0.36020(12) -0.06242(8) 0.0180(2) Uani 1 1 d . . . H11A H 0.3536 0.3167 -0.1168 0.022 Uiso 1 1 calc R . . C12 C 0.30851(7) 0.32424(10) -0.00465(8) 0.0153(2) Uani 1 1 d . . . C13 C 0.25502(7) 0.22107(11) -0.02486(8) 0.0170(2) Uani 1 1 d . . . H13A H 0.2770 0.1535 -0.0530 0.020 Uiso 1 1 calc R . . H13B H 0.2109 0.2485 -0.0688 0.020 Uiso 1 1 calc R . . C14 C 0.27156(8) 0.56215(11) 0.29763(9) 0.0215(2) Uani 1 1 d . . . H14A H 0.2946 0.4976 0.3400 0.026 Uiso 1 1 calc R . . H14B H 0.2192 0.5644 0.2993 0.026 Uiso 1 1 calc R . . C15 C 0.30581(10) 0.68399(12) 0.33238(10) 0.0288(3) Uani 1 1 d . . . H15A H 0.3578 0.6831 0.3314 0.043 Uiso 1 1 calc R . . H15B H 0.3000 0.6973 0.3947 0.043 Uiso 1 1 calc R . . H15C H 0.2816 0.7495 0.2932 0.043 Uiso 1 1 calc R . . C16 C 0.24158(7) 0.62202(11) 0.13731(9) 0.0212(2) Uani 1 1 d . . . H16A H 0.2433 0.5949 0.0751 0.025 Uiso 1 1 calc R . . H16B H 0.2695 0.6987 0.1491 0.025 Uiso 1 1 calc R . . C17 C 0.16302(8) 0.64717(13) 0.14108(11) 0.0282(3) Uani 1 1 d . . . H17A H 0.1364 0.5703 0.1387 0.042 Uiso 1 1 calc R . . H17B H 0.1404 0.6979 0.0892 0.042 Uiso 1 1 calc R . . H17C H 0.1614 0.6896 0.1978 0.042 Uiso 1 1 calc R . . C18 C 0.13528(7) 0.09949(12) 0.03462(9) 0.0201(2) Uani 1 1 d . . . C19 C 0.08019(7) 0.20413(14) 0.01418(11) 0.0294(3) Uani 1 1 d . . . H19A H 0.0947 0.2601 -0.0293 0.044 Uiso 1 1 calc R . . H19B H 0.0790 0.2477 0.0706 0.044 Uiso 1 1 calc R . . H19C H 0.0317 0.1714 -0.0118 0.044 Uiso 1 1 calc R . . C20 C 0.12982(7) 0.02702(12) -0.05392(9) 0.0237(3) Uani 1 1 d . . . H20A H 0.0803 -0.0051 -0.0738 0.036 Uiso 1 1 calc R . . H20B H 0.1647 -0.0404 -0.0433 0.036 Uiso 1 1 calc R . . H20C H 0.1410 0.0804 -0.1011 0.036 Uiso 1 1 calc R . . C21 C 0.11326(8) 0.01728(13) 0.10678(10) 0.0261(3) Uani 1 1 d . . . H21A H 0.1207 0.0608 0.1648 0.039 Uiso 1 1 calc R . . H21B H 0.1433 -0.0564 0.1143 0.039 Uiso 1 1 calc R . . H21C H 0.0618 -0.0050 0.0872 0.039 Uiso 1 1 calc R . . C22 C 0.29547(7) 0.04045(11) 0.12197(8) 0.0177(2) Uani 1 1 d . . . C23 C 0.37145(7) 0.09711(12) 0.13049(9) 0.0224(2) Uani 1 1 d . . . H23A H 0.4088 0.0381 0.1580 0.034 Uiso 1 1 calc R . . H23B H 0.3755 0.1697 0.1689 0.034 Uiso 1 1 calc R . . H23C H 0.3785 0.1196 0.0700 0.034 Uiso 1 1 calc R . . C24 C 0.28864(8) 0.00308(12) 0.21809(9) 0.0243(3) Uani 1 1 d . . . H24A H 0.2428 -0.0410 0.2147 0.036 Uiso 1 1 calc R . . H24B H 0.2891 0.0758 0.2557 0.036 Uiso 1 1 calc R . . H24C H 0.3297 -0.0494 0.2452 0.036 Uiso 1 1 calc R . . C25 C 0.28985(7) -0.07095(11) 0.06019(9) 0.0213(2) Uani 1 1 d . . . H25A H 0.3305 -0.1261 0.0834 0.032 Uiso 1 1 calc R . . H25B H 0.2918 -0.0452 -0.0015 0.032 Uiso 1 1 calc R . . H25C H 0.2437 -0.1129 0.0591 0.032 Uiso 1 1 calc R . . O3 O 0.1537(2) 0.7130(5) 0.8774(3) 0.0568(11) Uani 0.50 1 d PD A 1 C26 C 0.1053(3) 0.6397(7) 0.8568(4) 0.0358(13) Uani 0.50 1 d PD A 1 C27 C 0.0360(2) 0.6589(4) 0.7864(3) 0.0359(8) Uani 0.50 1 d PD A 1 H27A H 0.0469 0.6801 0.7269 0.043 Uiso 0.50 1 calc PR A 1 H27B H 0.0064 0.7247 0.8051 0.043 Uiso 0.50 1 calc PR A 1 C28 C -0.0037(3) 0.5381(5) 0.7813(3) 0.0318(9) Uani 0.50 1 d PD A 1 H28A H 0.0092 0.4854 0.7339 0.038 Uiso 0.50 1 calc PR A 1 H28B H -0.0572 0.5504 0.7675 0.038 Uiso 0.50 1 calc PR A 1 C29 C 0.0224(3) 0.4824(6) 0.8759(3) 0.0339(10) Uani 0.50 1 d PD A 1 H29A H -0.0035 0.5185 0.9203 0.041 Uiso 0.50 1 calc PR A 1 H29B H 0.0152 0.3933 0.8745 0.041 Uiso 0.50 1 calc PR A 1 C30 C 0.1036(3) 0.5151(7) 0.8988(5) 0.0346(13) Uani 0.50 1 d PD A 1 H30A H 0.1226 0.5179 0.9654 0.041 Uiso 0.50 1 calc PR A 1 H30B H 0.1325 0.4560 0.8718 0.041 Uiso 0.50 1 calc PR A 1 O3A O 0.1781(2) 0.7158(4) 0.9150(3) 0.0497(9) Uani 0.50 1 d PD B 2 C26A C 0.1262(3) 0.6519(5) 0.8833(4) 0.0310(11) Uani 0.50 1 d PD B 2 C27A C 0.1260(3) 0.5145(7) 0.8909(6) 0.0333(12) Uani 0.50 1 d PD B 2 H27C H 0.1460 0.4880 0.9542 0.040 Uiso 0.50 1 calc PR B 2 H27D H 0.1550 0.4770 0.8505 0.040 Uiso 0.50 1 calc PR B 2 C28A C 0.0455(3) 0.4811(6) 0.8610(5) 0.0448(13) Uani 0.50 1 d PD B 2 H28C H 0.0396 0.4009 0.8306 0.054 Uiso 0.50 1 calc PR B 2 H28D H 0.0219 0.4788 0.9137 0.054 Uiso 0.50 1 calc PR B 2 C29A C 0.0132(3) 0.5805(6) 0.7956(4) 0.058(2) Uani 0.50 1 d PD B 2 H29C H 0.0204 0.5625 0.7338 0.069 Uiso 0.50 1 calc PR B 2 H29D H -0.0397 0.5888 0.7930 0.069 Uiso 0.50 1 calc PR B 2 C30A C 0.0530(3) 0.6947(4) 0.8320(4) 0.0467(10) Uani 0.50 1 d PD B 2 H30C H 0.0582 0.7496 0.7818 0.056 Uiso 0.50 1 calc PR B 2 H30D H 0.0267 0.7381 0.8728 0.056 Uiso 0.50 1 calc PR B 2 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 P1 0.01390(13) 0.01250(13) 0.01570(14) 0.00032(9) 0.00203(10) -0.00117(9) Ru1 0.01405(5) 0.01177(5) 0.01493(5) 0.00075(3) 0.00419(4) -0.00034(3) O1 0.0222(4) 0.0276(5) 0.0226(4) -0.0006(4) 0.0097(4) -0.0035(4) O2 0.0181(4) 0.0161(4) 0.0171(4) 0.0025(3) 0.0009(3) -0.0040(3) N1 0.0156(4) 0.0136(4) 0.0146(4) 0.0010(3) 0.0036(3) -0.0002(3) N2 0.0214(5) 0.0135(4) 0.0174(4) 0.0010(3) 0.0083(4) 0.0007(4) C1 0.0184(5) 0.0153(5) 0.0180(5) -0.0013(4) 0.0033(4) -0.0001(4) C2 0.0189(5) 0.0153(5) 0.0159(5) -0.0004(4) 0.0024(4) -0.0032(4) C3 0.0246(6) 0.0228(6) 0.0180(5) -0.0025(4) 0.0021(5) -0.0049(5) C4 0.0247(6) 0.0273(6) 0.0208(6) 0.0038(5) -0.0018(5) -0.0066(5) C5 0.0219(6) 0.0224(6) 0.0262(6) 0.0010(5) -0.0033(5) -0.0011(5) C6 0.0177(5) 0.0193(5) 0.0213(6) -0.0013(4) 0.0021(4) -0.0020(4) C7 0.0193(5) 0.0141(5) 0.0169(5) -0.0007(4) 0.0056(4) -0.0034(4) C8 0.0159(5) 0.0147(5) 0.0168(5) 0.0009(4) 0.0036(4) -0.0005(4) C9 0.0186(5) 0.0191(5) 0.0191(5) 0.0001(4) 0.0049(4) -0.0040(4) C10 0.0190(5) 0.0241(6) 0.0181(5) 0.0014(4) 0.0074(4) -0.0019(5) C11 0.0179(5) 0.0209(5) 0.0155(5) 0.0001(4) 0.0046(4) 0.0011(4) C12 0.0149(5) 0.0151(5) 0.0152(5) 0.0005(4) 0.0019(4) 0.0013(4) C13 0.0184(5) 0.0162(5) 0.0159(5) -0.0008(4) 0.0027(4) -0.0023(4) C14 0.0316(7) 0.0152(5) 0.0212(6) 0.0002(4) 0.0130(5) -0.0001(5) C15 0.0492(9) 0.0164(6) 0.0243(6) -0.0028(5) 0.0157(6) -0.0033(6) C16 0.0252(6) 0.0141(5) 0.0254(6) 0.0050(4) 0.0081(5) 0.0024(4) C17 0.0285(7) 0.0231(6) 0.0358(8) 0.0060(5) 0.0128(6) 0.0086(5) C18 0.0165(5) 0.0192(5) 0.0236(6) -0.0001(4) 0.0018(4) -0.0043(4) C19 0.0158(6) 0.0266(7) 0.0420(8) -0.0024(6) -0.0023(5) -0.0013(5) C20 0.0234(6) 0.0240(6) 0.0218(6) -0.0019(5) 0.0008(5) -0.0071(5) C21 0.0239(6) 0.0285(7) 0.0268(6) -0.0021(5) 0.0075(5) -0.0104(5) C22 0.0197(5) 0.0139(5) 0.0182(5) -0.0005(4) 0.0012(4) 0.0010(4) C23 0.0178(5) 0.0173(5) 0.0296(6) -0.0007(5) -0.0006(5) 0.0022(4) C24 0.0322(7) 0.0200(6) 0.0191(6) 0.0034(4) 0.0019(5) 0.0034(5) C25 0.0257(6) 0.0146(5) 0.0227(6) -0.0016(4) 0.0035(5) 0.0008(5) O3 0.045(2) 0.046(2) 0.077(3) -0.001(2) 0.0089(19) -0.0141(19) C26 0.035(3) 0.031(2) 0.043(3) -0.003(2) 0.013(2) -0.004(2) C27 0.0286(18) 0.028(2) 0.053(3) 0.0139(16) 0.0125(17) 0.0034(14) C28 0.031(2) 0.043(2) 0.0216(18) 0.0073(16) 0.0055(15) 0.0072(17) C29 0.032(3) 0.037(2) 0.0297(18) 0.0081(14) -0.0003(17) -0.009(2) C30 0.036(3) 0.030(2) 0.032(2) 0.0061(16) -0.005(2) -0.003(2) O3A 0.056(3) 0.0354(16) 0.060(2) 0.0004(18) 0.0180(17) -0.0129(18) C26A 0.041(3) 0.024(2) 0.033(3) 0.0028(19) 0.018(2) -0.002(2) C27A 0.033(3) 0.0292(19) 0.036(2) -0.0022(15) 0.003(2) 0.004(2) C28A 0.034(3) 0.037(2) 0.062(3) 0.001(2) 0.007(2) 0.000(2) C29A 0.044(3) 0.072(5) 0.048(3) -0.018(3) -0.011(2) 0.030(3) C30A 0.046(2) 0.039(2) 0.061(3) 0.015(2) 0.023(2) 0.0156(19) _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 P1 C13 1.8586(12) . ? P1 C22 1.8804(12) . ? P1 C18 1.8920(12) . ? P1 Ru1 2.2556(3) . ? Ru1 C1 1.8275(12) . ? Ru1 N1 2.0940(10) . ? Ru1 O2 2.1991(9) . ? Ru1 N2 2.2394(10) . ? Ru1 H1 1.534(19) . ? O1 C1 1.1672(15) . ? O2 C2 1.3867(14) . ? N1 C8 1.3454(15) . ? N1 C12 1.3475(15) . ? N2 C14 1.4950(15) . ? N2 C16 1.4995(16) . ? N2 C7 1.5091(15) . ? C2 C6 1.5525(17) . ? C2 C3 1.5619(17) . ? C2 C7 1.5816(17) . ? C3 C4 1.543(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.547(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5310(18) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5083(16) . ? C7 H7A 1.0000 . ? C8 C9 1.3874(16) . ? C9 C10 1.3933(17) . ? C9 H9A 0.9500 . ? C10 C11 1.3935(18) . ? C10 H10A 0.9500 . ? C11 C12 1.3914(17) . ? C11 H11A 0.9500 . ? C12 C13 1.5037(16) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5307(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.5146(19) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.5350(19) . ? C18 C21 1.5386(18) . ? C18 C20 1.5391(18) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C25 1.5299(17) . ? C22 C23 1.5375(18) . ? C22 C24 1.5376(18) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? O3 C26 1.206(6) . ? C26 C27 1.506(7) . ? C26 C30 1.514(10) . ? C27 C28 1.519(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.533(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.532(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? O3A C26A 1.214(6) . ? C26A C30A 1.501(7) . ? C26A C27A 1.518(9) . ? C27A C28A 1.527(8) . ? C27A H27C 0.9900 . ? C27A H27D 0.9900 . ? C28A C29A 1.510(8) . ? C28A H28C 0.9900 . ? C28A H28D 0.9900 . ? C29A C30A 1.505(7) . ? C29A H29C 0.9900 . ? C29A H29D 0.9900 . ? C30A H30C 0.9900 . ? C30A H30D 0.9900 . ? 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 C13 P1 C22 104.20(6) . . ? C13 P1 C18 102.23(6) . . ? C22 P1 C18 109.62(6) . . ? C13 P1 Ru1 100.60(4) . . ? C22 P1 Ru1 115.40(4) . . ? C18 P1 Ru1 121.73(4) . . ? C1 Ru1 N1 174.54(5) . . ? C1 Ru1 O2 99.49(4) . . ? N1 Ru1 O2 84.52(4) . . ? C1 Ru1 N2 107.92(4) . . ? N1 Ru1 N2 76.60(4) . . ? O2 Ru1 N2 75.18(4) . . ? C1 Ru1 P1 93.43(4) . . ? N1 Ru1 P1 81.79(3) . . ? O2 Ru1 P1 107.46(2) . . ? N2 Ru1 P1 157.91(3) . . ? C1 Ru1 H1 87.4(7) . . ? N1 Ru1 H1 89.3(7) . . ? O2 Ru1 H1 167.0(7) . . ? N2 Ru1 H1 92.3(7) . . ? P1 Ru1 H1 82.9(7) . . ? C2 O2 Ru1 113.59(7) . . ? C8 N1 C12 121.38(10) . . ? C8 N1 Ru1 115.09(8) . . ? C12 N1 Ru1 123.53(8) . . ? C14 N2 C16 109.81(10) . . ? C14 N2 C7 111.96(10) . . ? C16 N2 C7 108.50(9) . . ? C14 N2 Ru1 114.04(7) . . ? C16 N2 Ru1 114.25(8) . . ? C7 N2 Ru1 97.67(7) . . ? O1 C1 Ru1 175.02(11) . . ? O2 C2 C6 112.06(10) . . ? O2 C2 C3 111.26(10) . . ? C6 C2 C3 98.64(10) . . ? O2 C2 C7 109.79(9) . . ? C6 C2 C7 110.18(9) . . ? C3 C2 C7 114.56(10) . . ? C4 C3 C2 104.69(10) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? C3 C4 C5 105.31(10) . . ? C3 C4 H4A 110.7 . . ? C5 C4 H4A 110.7 . . ? C3 C4 H4B 110.7 . . ? C5 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? C6 C5 C4 105.23(11) . . ? C6 C5 H5A 110.7 . . ? C4 C5 H5A 110.7 . . ? C6 C5 H5B 110.7 . . ? C4 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? C5 C6 C2 103.65(10) . . ? C5 C6 H6A 111.0 . . ? C2 C6 H6A 111.0 . . ? C5 C6 H6B 111.0 . . ? C2 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? C8 C7 N2 106.47(9) . . ? C8 C7 C2 107.18(9) . . ? N2 C7 C2 110.20(9) . . ? C8 C7 H7A 110.9 . . ? N2 C7 H7A 110.9 . . ? C2 C7 H7A 110.9 . . ? N1 C8 C9 120.69(11) . . ? N1 C8 C7 112.40(10) . . ? C9 C8 C7 126.68(11) . . ? C8 C9 C10 118.48(11) . . ? C8 C9 H9A 120.8 . . ? C10 C9 H9A 120.8 . . ? C9 C10 C11 120.37(11) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C12 C11 C10 118.20(11) . . ? C12 C11 H11A 120.9 . . ? C10 C11 H11A 120.9 . . ? N1 C12 C11 120.73(11) . . ? N1 C12 C13 115.51(10) . . ? C11 C12 C13 123.75(11) . . ? C12 C13 P1 111.19(8) . . ? C12 C13 H13A 109.4 . . ? P1 C13 H13A 109.4 . . ? C12 C13 H13B 109.4 . . ? P1 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? N2 C14 C15 115.44(10) . . ? N2 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? N2 C14 H14B 108.4 . . ? C15 C14 H14B 108.4 . . ? H14A C14 H14B 107.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 C17 114.29(11) . . ? N2 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? N2 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? 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 . . ? C19 C18 C21 108.14(12) . . ? C19 C18 C20 107.40(11) . . ? C21 C18 C20 109.25(10) . . ? C19 C18 P1 108.39(9) . . ? C21 C18 P1 109.95(9) . . ? C20 C18 P1 113.55(9) . . ? 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 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C25 C22 C23 108.50(10) . . ? C25 C22 C24 110.48(10) . . ? C23 C22 C24 107.11(10) . . ? C25 C22 P1 115.65(8) . . ? C23 C22 P1 105.57(8) . . ? C24 C22 P1 109.10(9) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O3 C26 C27 125.2(6) . . ? O3 C26 C30 125.6(6) . . ? C27 C26 C30 109.2(5) . . ? C26 C27 C28 104.7(4) . . ? C26 C27 H27A 110.8 . . ? C28 C27 H27A 110.8 . . ? C26 C27 H27B 110.8 . . ? C28 C27 H27B 110.8 . . ? H27A C27 H27B 108.9 . . ? C27 C28 C29 104.3(4) . . ? C27 C28 H28A 110.9 . . ? C29 C28 H28A 110.9 . . ? C27 C28 H28B 110.9 . . ? C29 C28 H28B 110.9 . . ? H28A C28 H28B 108.9 . . ? C30 C29 C28 102.6(4) . . ? C30 C29 H29A 111.2 . . ? C28 C29 H29A 111.2 . . ? C30 C29 H29B 111.2 . . ? C28 C29 H29B 111.2 . . ? H29A C29 H29B 109.2 . . ? C26 C30 C29 103.2(5) . . ? C26 C30 H30A 111.1 . . ? C29 C30 H30A 111.1 . . ? C26 C30 H30B 111.1 . . ? C29 C30 H30B 111.1 . . ? H30A C30 H30B 109.1 . . ? O3A C26A C30A 126.2(6) . . ? O3A C26A C27A 124.3(6) . . ? C30A C26A C27A 109.6(5) . . ? C26A C27A C28A 103.6(5) . . ? C26A C27A H27C 111.0 . . ? C28A C27A H27C 111.0 . . ? C26A C27A H27D 111.0 . . ? C28A C27A H27D 111.0 . . ? H27C C27A H27D 109.0 . . ? C29A C28A C27A 104.6(5) . . ? C29A C28A H28C 110.8 . . ? C27A C28A H28C 110.8 . . ? C29A C28A H28D 110.8 . . ? C27A C28A H28D 110.8 . . ? H28C C28A H28D 108.9 . . ? C30A C29A C28A 105.7(4) . . ? C30A C29A H29C 110.6 . . ? C28A C29A H29C 110.6 . . ? C30A C29A H29D 110.6 . . ? C28A C29A H29D 110.6 . . ? H29C C29A H29D 108.7 . . ? C26A C30A C29A 104.7(4) . . ? C26A C30A H30C 110.8 . . ? C29A C30A H30C 110.8 . . ? C26A C30A H30D 110.8 . . ? C29A C30A H30D 110.8 . . ? H30C C30A H30D 108.9 . . ? 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 C13 P1 Ru1 C1 156.88(5) . . . . ? C22 P1 Ru1 C1 -91.70(6) . . . . ? C18 P1 Ru1 C1 45.22(6) . . . . ? C13 P1 Ru1 N1 -20.47(5) . . . . ? C22 P1 Ru1 N1 90.95(5) . . . . ? C18 P1 Ru1 N1 -132.13(6) . . . . ? C13 P1 Ru1 O2 -102.05(5) . . . . ? C22 P1 Ru1 O2 9.37(5) . . . . ? C18 P1 Ru1 O2 146.29(5) . . . . ? C13 P1 Ru1 N2 -8.48(9) . . . . ? C22 P1 Ru1 N2 102.93(9) . . . . ? C18 P1 Ru1 N2 -120.14(9) . . . . ? C1 Ru1 O2 C2 -138.80(8) . . . . ? N1 Ru1 O2 C2 44.93(8) . . . . ? N2 Ru1 O2 C2 -32.63(8) . . . . ? P1 Ru1 O2 C2 124.53(7) . . . . ? C1 Ru1 N1 C8 166.3(5) . . . . ? O2 Ru1 N1 C8 -56.10(8) . . . . ? N2 Ru1 N1 C8 19.94(8) . . . . ? P1 Ru1 N1 C8 -164.66(8) . . . . ? C1 Ru1 N1 C12 -14.0(5) . . . . ? O2 Ru1 N1 C12 123.66(9) . . . . ? N2 Ru1 N1 C12 -160.30(10) . . . . ? P1 Ru1 N1 C12 15.10(9) . . . . ? C1 Ru1 N2 C14 23.65(10) . . . . ? N1 Ru1 N2 C14 -159.52(9) . . . . ? O2 Ru1 N2 C14 -71.73(8) . . . . ? P1 Ru1 N2 C14 -171.72(6) . . . . ? C1 Ru1 N2 C16 -103.79(9) . . . . ? N1 Ru1 N2 C16 73.04(8) . . . . ? O2 Ru1 N2 C16 160.83(9) . . . . ? P1 Ru1 N2 C16 60.84(12) . . . . ? C1 Ru1 N2 C7 141.90(7) . . . . ? N1 Ru1 N2 C7 -41.28(6) . . . . ? O2 Ru1 N2 C7 46.51(6) . . . . ? P1 Ru1 N2 C7 -53.48(11) . . . . ? N1 Ru1 C1 O1 4.3(16) . . . . ? O2 Ru1 C1 O1 -132.8(13) . . . . ? N2 Ru1 C1 O1 149.8(13) . . . . ? P1 Ru1 C1 O1 -24.4(13) . . . . ? Ru1 O2 C2 C6 -114.40(9) . . . . ? Ru1 O2 C2 C3 136.24(8) . . . . ? Ru1 O2 C2 C7 8.37(11) . . . . ? O2 C2 C3 C4 75.36(13) . . . . ? C6 C2 C3 C4 -42.45(12) . . . . ? C7 C2 C3 C4 -159.39(10) . . . . ? C2 C3 C4 C5 23.24(13) . . . . ? C3 C4 C5 C6 5.95(14) . . . . ? C4 C5 C6 C2 -33.15(13) . . . . ? O2 C2 C6 C5 -70.99(12) . . . . ? C3 C2 C6 C5 46.22(11) . . . . ? C7 C2 C6 C5 166.46(10) . . . . ? C14 N2 C7 C8 177.52(9) . . . . ? C16 N2 C7 C8 -61.13(12) . . . . ? Ru1 N2 C7 C8 57.69(9) . . . . ? C14 N2 C7 C2 61.62(12) . . . . ? C16 N2 C7 C2 -177.03(9) . . . . ? Ru1 N2 C7 C2 -58.21(9) . . . . ? O2 C2 C7 C8 -79.50(12) . . . . ? C6 C2 C7 C8 44.38(12) . . . . ? C3 C2 C7 C8 154.49(10) . . . . ? O2 C2 C7 N2 35.96(12) . . . . ? C6 C2 C7 N2 159.83(9) . . . . ? C3 C2 C7 N2 -90.05(12) . . . . ? C12 N1 C8 C9 3.56(17) . . . . ? Ru1 N1 C8 C9 -176.68(9) . . . . ? C12 N1 C8 C7 -171.25(10) . . . . ? Ru1 N1 C8 C7 8.52(12) . . . . ? N2 C7 C8 N1 -47.95(12) . . . . ? C2 C7 C8 N1 69.97(12) . . . . ? N2 C7 C8 C9 137.62(12) . . . . ? C2 C7 C8 C9 -104.46(13) . . . . ? N1 C8 C9 C10 -2.81(18) . . . . ? C7 C8 C9 C10 171.19(12) . . . . ? C8 C9 C10 C11 -0.59(19) . . . . ? C9 C10 C11 C12 3.21(18) . . . . ? C8 N1 C12 C11 -0.80(17) . . . . ? Ru1 N1 C12 C11 179.46(9) . . . . ? C8 N1 C12 C13 -179.80(10) . . . . ? Ru1 N1 C12 C13 0.46(14) . . . . ? C10 C11 C12 N1 -2.57(18) . . . . ? C10 C11 C12 C13 176.35(11) . . . . ? N1 C12 C13 P1 -20.35(13) . . . . ? C11 C12 C13 P1 160.68(10) . . . . ? C22 P1 C13 C12 -92.02(9) . . . . ? C18 P1 C13 C12 153.83(8) . . . . ? Ru1 P1 C13 C12 27.81(9) . . . . ? C16 N2 C14 C15 -60.08(15) . . . . ? C7 N2 C14 C15 60.51(14) . . . . ? Ru1 N2 C14 C15 170.23(10) . . . . ? C14 N2 C16 C17 -54.25(15) . . . . ? C7 N2 C16 C17 -176.91(11) . . . . ? Ru1 N2 C16 C17 75.33(12) . . . . ? C13 P1 C18 C19 -78.06(10) . . . . ? C22 P1 C18 C19 171.83(9) . . . . ? Ru1 P1 C18 C19 32.75(11) . . . . ? C13 P1 C18 C21 163.93(9) . . . . ? C22 P1 C18 C21 53.82(11) . . . . ? Ru1 P1 C18 C21 -85.26(9) . . . . ? C13 P1 C18 C20 41.19(10) . . . . ? C22 P1 C18 C20 -68.92(10) . . . . ? Ru1 P1 C18 C20 152.00(8) . . . . ? C13 P1 C22 C25 -65.13(10) . . . . ? C18 P1 C22 C25 43.66(11) . . . . ? Ru1 P1 C22 C25 -174.41(8) . . . . ? C13 P1 C22 C23 54.81(9) . . . . ? C18 P1 C22 C23 163.61(8) . . . . ? Ru1 P1 C22 C23 -54.47(9) . . . . ? C13 P1 C22 C24 169.63(8) . . . . ? C18 P1 C22 C24 -81.58(10) . . . . ? Ru1 P1 C22 C24 60.35(9) . . . . ? O3 C26 C27 C28 176.1(7) . . . . ? C30 C26 C27 C28 -5.2(6) . . . . ? C26 C27 C28 C29 27.8(5) . . . . ? C27 C28 C29 C30 -39.8(6) . . . . ? O3 C26 C30 C29 159.4(7) . . . . ? C27 C26 C30 C29 -19.3(7) . . . . ? C28 C29 C30 C26 35.8(6) . . . . ? O3A C26A C27A C28A 167.3(6) . . . . ? C30A C26A C27A C28A -12.2(7) . . . . ? C26A C27A C28A C29A 28.8(7) . . . . ? C27A C28A C29A C30A -35.5(6) . . . . ? O3A C26A C30A C29A 171.3(6) . . . . ? C27A C26A C30A C29A -9.1(6) . . . . ? C28A C29A C30A C26A 27.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.62 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.063 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 936846' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ch761d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H41 N2 O2 P Ru' _chemical_formula_weight 557.66 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)/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 16.0967(8) _cell_length_b 10.6978(5) _cell_length_c 16.1908(8) _cell_angle_alpha 90.00 _cell_angle_beta 108.5780(10) _cell_angle_gamma 90.00 _cell_volume 2642.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 9969 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.32 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.680 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8817 _exptl_absorpt_correction_T_max 0.9865 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2008/1) Bruker AXS area detector absorption and other corrections, University of Gottingen, Germany 2008. ; _exptl_special_details ; 2053 frames x 90 sec @ 5.070 cm; 0.5 deg. steps in omega, 0.45 deg phi, 50kV/30mA ; _diffrn_ambient_temperature 85(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 39378 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.32 _reflns_number_total 5945 _reflns_number_gt 4686 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-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^)+(0.0359P)^2^+1.5126P] 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 5945 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0660 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 P1 P 0.69703(4) 0.86925(6) 0.89981(4) 0.01495(13) Uani 1 1 d . . . Ru1 Ru 0.693675(12) 0.685944(17) 0.965953(11) 0.01395(6) Uani 1 1 d . . . H1 H 0.6007(19) 0.673(3) 0.8950(18) 0.035(8) Uiso 1 1 d . . . O1 O 0.61048(11) 0.79260(15) 1.09191(11) 0.0209(4) Uani 1 1 d . . . O2 O 0.82642(11) 0.65353(14) 1.06140(10) 0.0175(3) Uani 1 1 d . . . N1 N 0.70241(12) 0.48160(18) 0.98898(12) 0.0155(4) Uani 1 1 d . . . N2 N 0.74874(12) 0.62268(18) 0.87276(12) 0.0159(4) Uani 1 1 d . . . C1 C 0.64323(15) 0.7485(2) 1.04380(15) 0.0172(5) Uani 1 1 d . . . C2 C 0.86191(15) 0.5429(2) 1.04551(15) 0.0167(5) Uani 1 1 d . . . H2A H 0.9071 0.5648 1.0175 0.020 Uiso 1 1 calc R . . C3 C 0.90837(15) 0.4649(2) 1.12657(15) 0.0175(5) Uani 1 1 d . . . C4 C 0.91247(15) 0.5024(2) 1.20935(15) 0.0175(5) Uani 1 1 d . . . H4A H 0.8866 0.5795 1.2171 0.021 Uiso 1 1 calc R . . C5 C 0.95414(16) 0.4284(2) 1.28183(16) 0.0203(5) Uani 1 1 d . . . H5A H 0.9573 0.4563 1.3385 0.024 Uiso 1 1 calc R . . C6 C 0.99089(16) 0.3145(2) 1.27175(15) 0.0206(5) Uani 1 1 d . . . H6A H 1.0178 0.2631 1.3208 0.025 Uiso 1 1 calc R . . C7 C 0.98771(16) 0.2771(2) 1.18885(16) 0.0230(5) Uani 1 1 d . . . H7A H 1.0125 0.1992 1.1810 0.028 Uiso 1 1 calc R . . C8 C 0.94863(16) 0.3523(2) 1.11743(16) 0.0212(5) Uani 1 1 d . . . H8A H 0.9492 0.3270 1.0614 0.025 Uiso 1 1 calc R . . C9 C 0.79000(15) 0.4606(2) 0.97726(14) 0.0166(5) Uani 1 1 d . . . H9A H 0.8062 0.3700 0.9833 0.020 Uiso 1 1 calc R . . C10 C 0.78690(15) 0.5095(2) 0.88957(15) 0.0173(5) Uani 1 1 d . . . C11 C 0.82918(16) 0.4577(2) 0.83519(15) 0.0199(5) Uani 1 1 d . . . H11A H 0.8552 0.3772 0.8465 0.024 Uiso 1 1 calc R . . C12 C 0.83232(16) 0.5270(2) 0.76387(15) 0.0212(5) Uani 1 1 d . . . H12A H 0.8612 0.4941 0.7258 0.025 Uiso 1 1 calc R . . C13 C 0.79357(16) 0.6443(2) 0.74773(15) 0.0205(5) Uani 1 1 d . . . H13A H 0.7962 0.6922 0.6992 0.025 Uiso 1 1 calc R . . C14 C 0.75109(15) 0.6903(2) 0.80324(14) 0.0168(5) Uani 1 1 d . . . C15 C 0.70559(16) 0.8150(2) 0.79333(14) 0.0183(5) Uani 1 1 d . . . H15A H 0.6462 0.8078 0.7504 0.022 Uiso 1 1 calc R . . H15B H 0.7388 0.8772 0.7711 0.022 Uiso 1 1 calc R . . C16 C 0.70147(16) 0.4511(2) 1.07903(14) 0.0174(5) Uani 1 1 d . . . H16A H 0.6439 0.4765 1.0834 0.021 Uiso 1 1 calc R . . H16B H 0.7466 0.5031 1.1208 0.021 Uiso 1 1 calc R . . C17 C 0.71750(17) 0.3150(2) 1.10809(16) 0.0220(5) Uani 1 1 d . . . H17A H 0.6692 0.2631 1.0723 0.033 Uiso 1 1 calc R . . H17B H 0.7209 0.3081 1.1694 0.033 Uiso 1 1 calc R . . H17C H 0.7727 0.2863 1.1012 0.033 Uiso 1 1 calc R . . C18 C 0.63651(15) 0.4053(2) 0.92213(15) 0.0180(5) Uani 1 1 d . . . H18A H 0.6555 0.3168 0.9289 0.022 Uiso 1 1 calc R . . H18B H 0.6357 0.4330 0.8635 0.022 Uiso 1 1 calc R . . C19 C 0.54416(16) 0.4129(2) 0.92700(16) 0.0224(5) Uani 1 1 d . . . H19A H 0.5424 0.3742 0.9813 0.034 Uiso 1 1 calc R . . H19B H 0.5039 0.3688 0.8772 0.034 Uiso 1 1 calc R . . H19C H 0.5265 0.5008 0.9257 0.034 Uiso 1 1 calc R . . C20 C 0.59838(16) 0.9753(2) 0.86604(15) 0.0194(5) Uani 1 1 d . . . C21 C 0.51455(16) 0.8954(2) 0.83641(17) 0.0254(6) Uani 1 1 d . . . H21A H 0.4632 0.9502 0.8165 0.038 Uiso 1 1 calc R . . H21B H 0.5106 0.8445 0.8853 0.038 Uiso 1 1 calc R . . H21C H 0.5165 0.8406 0.7886 0.038 Uiso 1 1 calc R . . C22 C 0.59672(18) 1.0639(2) 0.79046(16) 0.0243(5) Uani 1 1 d . . . H22A H 0.6025 1.0149 0.7414 0.036 Uiso 1 1 calc R . . H22B H 0.6455 1.1232 0.8099 0.036 Uiso 1 1 calc R . . H22C H 0.5411 1.1097 0.7720 0.036 Uiso 1 1 calc R . . C23 C 0.59550(17) 1.0529(2) 0.94506(16) 0.0215(5) Uani 1 1 d . . . H23A H 0.6468 1.1080 0.9636 0.032 Uiso 1 1 calc R . . H23B H 0.5960 0.9967 0.9930 0.032 Uiso 1 1 calc R . . H23C H 0.5419 1.1035 0.9289 0.032 Uiso 1 1 calc R . . C24 C 0.80063(15) 0.9626(2) 0.94944(15) 0.0172(5) Uani 1 1 d . . . C25 C 0.80573(17) 1.0895(2) 0.90736(16) 0.0203(5) Uani 1 1 d . . . H25A H 0.7615 1.1459 0.9165 0.030 Uiso 1 1 calc R . . H25B H 0.7948 1.0782 0.8447 0.030 Uiso 1 1 calc R . . H25C H 0.8642 1.1256 0.9339 0.030 Uiso 1 1 calc R . . C26 C 0.81368(16) 0.9800(2) 1.04699(15) 0.0198(5) Uani 1 1 d . . . H26A H 0.8680 1.0264 1.0742 0.030 Uiso 1 1 calc R . . H26B H 0.8173 0.8979 1.0748 0.030 Uiso 1 1 calc R . . H26C H 0.7640 1.0266 1.0541 0.030 Uiso 1 1 calc R . . C27 C 0.87633(15) 0.8793(2) 0.94347(16) 0.0199(5) Uani 1 1 d . . . H27A H 0.8714 0.8668 0.8821 0.030 Uiso 1 1 calc R . . H27B H 0.8735 0.7982 0.9706 0.030 Uiso 1 1 calc R . . H27C H 0.9324 0.9198 0.9739 0.030 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 P1 0.0173(3) 0.0140(3) 0.0130(3) 0.0000(2) 0.0040(2) -0.0001(2) Ru1 0.01577(10) 0.01328(9) 0.01257(9) -0.00030(7) 0.00420(7) 0.00006(8) O1 0.0219(9) 0.0236(9) 0.0196(9) -0.0010(7) 0.0100(7) 0.0014(7) O2 0.0197(9) 0.0138(8) 0.0174(8) -0.0007(6) 0.0037(7) 0.0011(6) N1 0.0167(10) 0.0153(10) 0.0138(10) -0.0017(7) 0.0039(8) -0.0013(8) N2 0.0171(10) 0.0157(10) 0.0142(10) -0.0006(7) 0.0041(8) -0.0006(8) C1 0.0172(12) 0.0130(12) 0.0186(12) 0.0036(9) 0.0020(10) -0.0025(9) C2 0.0150(12) 0.0191(12) 0.0167(12) 0.0015(9) 0.0061(9) 0.0001(9) C3 0.0147(12) 0.0182(12) 0.0189(12) -0.0002(9) 0.0045(10) -0.0019(9) C4 0.0144(11) 0.0167(12) 0.0207(12) -0.0016(9) 0.0045(10) -0.0008(9) C5 0.0198(13) 0.0250(13) 0.0159(12) -0.0012(9) 0.0053(10) -0.0016(10) C6 0.0186(12) 0.0237(12) 0.0185(12) 0.0056(10) 0.0047(10) 0.0009(10) C7 0.0216(13) 0.0211(13) 0.0247(13) -0.0001(10) 0.0052(11) 0.0051(10) C8 0.0197(13) 0.0241(13) 0.0198(12) -0.0013(10) 0.0064(10) 0.0026(10) C9 0.0193(12) 0.0149(11) 0.0161(11) -0.0002(9) 0.0060(10) 0.0012(9) C10 0.0180(12) 0.0175(12) 0.0156(11) -0.0011(9) 0.0043(9) -0.0020(9) C11 0.0192(12) 0.0196(12) 0.0197(12) -0.0033(9) 0.0045(10) 0.0019(10) C12 0.0217(13) 0.0286(14) 0.0146(12) -0.0048(9) 0.0074(10) 0.0012(10) C13 0.0223(13) 0.0255(13) 0.0137(12) -0.0009(9) 0.0057(10) -0.0009(10) C14 0.0180(12) 0.0179(11) 0.0134(11) -0.0016(9) 0.0035(9) -0.0016(10) C15 0.0230(12) 0.0186(11) 0.0131(11) 0.0009(9) 0.0054(9) 0.0002(10) C16 0.0200(12) 0.0179(12) 0.0145(11) -0.0009(9) 0.0058(10) -0.0013(9) C17 0.0262(13) 0.0199(12) 0.0193(12) 0.0026(10) 0.0065(10) -0.0012(11) C18 0.0199(12) 0.0171(12) 0.0150(12) -0.0024(9) 0.0026(10) -0.0015(9) C19 0.0223(13) 0.0227(13) 0.0205(13) -0.0020(10) 0.0041(10) -0.0044(10) C20 0.0204(12) 0.0144(12) 0.0207(12) 0.0019(9) 0.0028(10) 0.0038(9) C21 0.0196(13) 0.0232(13) 0.0304(15) 0.0012(11) 0.0036(11) 0.0031(10) C22 0.0294(14) 0.0205(13) 0.0199(13) 0.0036(10) 0.0036(11) 0.0042(11) C23 0.0244(13) 0.0174(12) 0.0233(13) 0.0011(10) 0.0085(11) 0.0059(10) C24 0.0183(12) 0.0177(12) 0.0153(11) 0.0007(9) 0.0051(9) -0.0007(9) C25 0.0227(13) 0.0174(12) 0.0220(13) -0.0002(9) 0.0090(10) -0.0014(10) C26 0.0203(13) 0.0212(13) 0.0169(12) -0.0025(9) 0.0046(10) -0.0034(10) C27 0.0183(12) 0.0203(13) 0.0215(13) 0.0002(9) 0.0069(10) -0.0011(10) _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 P1 C15 1.865(2) . ? P1 C20 1.885(2) . ? P1 C24 1.890(2) . ? P1 Ru1 2.2432(6) . ? Ru1 H1 1.58(3) . ? Ru1 C1 1.830(2) . ? Ru1 N2 2.0911(19) . ? Ru1 N1 2.2146(19) . ? Ru1 O2 2.2293(16) . ? O1 C1 1.170(3) . ? O2 C2 1.374(3) . ? N1 C18 1.494(3) . ? N1 C9 1.498(3) . ? N1 C16 1.499(3) . ? N2 C10 1.346(3) . ? N2 C14 1.349(3) . ? C2 C3 1.534(3) . ? C2 C9 1.588(3) . ? C3 C4 1.380(3) . ? C3 C8 1.398(3) . ? C4 C5 1.397(3) . ? C5 C6 1.386(3) . ? C6 C7 1.386(3) . ? C7 C8 1.384(3) . ? C9 C10 1.499(3) . ? C10 C11 1.388(3) . ? C11 C12 1.387(3) . ? C12 C13 1.388(3) . ? C13 C14 1.382(3) . ? C14 C15 1.505(3) . ? C16 C17 1.527(3) . ? C18 C19 1.516(3) . ? C20 C23 1.538(3) . ? C20 C21 1.539(3) . ? C20 C22 1.541(3) . ? C24 C25 1.533(3) . ? C24 C26 1.537(3) . ? C24 C27 1.537(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 C15 P1 C20 102.86(11) . . ? C15 P1 C24 104.02(11) . . ? C20 P1 C24 110.66(11) . . ? C15 P1 Ru1 100.92(8) . . ? C20 P1 Ru1 121.23(8) . . ? C24 P1 Ru1 114.29(7) . . ? H1 Ru1 C1 90.4(10) . . ? H1 Ru1 N2 88.2(10) . . ? C1 Ru1 N2 176.95(9) . . ? H1 Ru1 N1 91.9(10) . . ? C1 Ru1 N1 105.27(8) . . ? N2 Ru1 N1 77.48(7) . . ? H1 Ru1 O2 166.0(10) . . ? C1 Ru1 O2 96.72(8) . . ? N2 Ru1 O2 85.23(7) . . ? N1 Ru1 O2 74.59(6) . . ? H1 Ru1 P1 83.6(10) . . ? C1 Ru1 P1 95.31(7) . . ? N2 Ru1 P1 81.85(6) . . ? N1 Ru1 P1 158.97(5) . . ? O2 Ru1 P1 107.66(4) . . ? C2 O2 Ru1 111.60(13) . . ? C18 N1 C9 107.80(17) . . ? C18 N1 C16 111.17(18) . . ? C9 N1 C16 113.09(17) . . ? C18 N1 Ru1 115.17(14) . . ? C9 N1 Ru1 97.97(13) . . ? C16 N1 Ru1 111.01(13) . . ? C10 N2 C14 121.3(2) . . ? C10 N2 Ru1 114.60(15) . . ? C14 N2 Ru1 124.03(15) . . ? O1 C1 Ru1 177.5(2) . . ? O2 C2 C3 115.27(19) . . ? O2 C2 C9 110.71(18) . . ? C3 C2 C9 110.04(18) . . ? C4 C3 C8 118.2(2) . . ? C4 C3 C2 122.2(2) . . ? C8 C3 C2 119.6(2) . . ? C3 C4 C5 120.8(2) . . ? C6 C5 C4 120.5(2) . . ? C7 C6 C5 118.9(2) . . ? C8 C7 C6 120.5(2) . . ? C7 C8 C3 121.0(2) . . ? N1 C9 C10 108.59(18) . . ? N1 C9 C2 109.60(17) . . ? C10 C9 C2 105.21(18) . . ? N2 C10 C11 121.0(2) . . ? N2 C10 C9 112.4(2) . . ? C11 C10 C9 125.9(2) . . ? C12 C11 C10 118.0(2) . . ? C11 C12 C13 120.4(2) . . ? C14 C13 C12 119.0(2) . . ? N2 C14 C13 120.2(2) . . ? N2 C14 C15 114.98(19) . . ? C13 C14 C15 124.8(2) . . ? C14 C15 P1 110.72(15) . . ? N1 C16 C17 116.99(19) . . ? N1 C18 C19 114.48(19) . . ? C23 C20 C21 107.6(2) . . ? C23 C20 C22 109.34(19) . . ? C21 C20 C22 107.6(2) . . ? C23 C20 P1 109.23(16) . . ? C21 C20 P1 109.27(16) . . ? C22 C20 P1 113.59(17) . . ? C25 C24 C26 109.92(19) . . ? C25 C24 C27 109.26(19) . . ? C26 C24 C27 106.44(19) . . ? C25 C24 P1 116.37(16) . . ? C26 C24 P1 108.30(15) . . ? C27 C24 P1 106.06(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.32 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.857 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 936847' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ch761e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H41 N2 O2 P Ru' _chemical_formula_weight 557.66 _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' 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 11.3568(3) _cell_length_b 14.7861(4) _cell_length_c 15.7682(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2647.84(12) _cell_formula_units_Z 4 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 9951 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 29.49 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.678 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8596 _exptl_absorpt_correction_T_max 0.9604 _exptl_absorpt_process_details ; Blessing, R. Acta Cryst. (1995) A51 33-38. Sheldrick, G. SADABS (Version 2008/1) Bruker AXS area detector absorption and other corrections, University of Gottingen, Germany 2008. ; _exptl_special_details ; 4095 frames x 15 sec. @ 5.070 cm; 0.5 deg. omega scans, 0.45 deg. phi ; _diffrn_ambient_temperature 85(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-I CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 100960 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 29.61 _reflns_number_total 7441 _reflns_number_gt 7084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-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^)+(0.0281P)^2^+0.6061P] 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 -0.043(17) _refine_ls_number_reflns 7441 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0553 _refine_ls_wR_factor_gt 0.0535 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.405329(12) 0.101777(9) 0.357030(9) 0.01387(4) Uani 1 1 d . . . H1 H 0.364(2) 0.0395(16) 0.4273(15) 0.026(6) Uiso 1 1 d . . . P1 P 0.57385(4) 0.02307(3) 0.37697(3) 0.01478(9) Uani 1 1 d . . . O1 O 0.44403(15) 0.23672(11) 0.49617(11) 0.0333(4) Uani 1 1 d . . . O2 O 0.43288(11) 0.18001(9) 0.23765(8) 0.0178(3) Uani 1 1 d . . . N1 N 0.22265(14) 0.12824(10) 0.31289(10) 0.0156(3) Uani 1 1 d . . . N2 N 0.37509(13) -0.00138(10) 0.27041(10) 0.0147(3) Uani 1 1 d . . . C1 C 0.43008(17) 0.18690(13) 0.43997(12) 0.0203(4) Uani 1 1 d . . . C2 C 0.24244(15) 0.11115(12) 0.21961(11) 0.0153(3) Uani 1 1 d . . . H2A H 0.1669 0.1162 0.1874 0.018 Uiso 1 1 calc R . . C3 C 0.33327(17) 0.18254(12) 0.18797(12) 0.0160(4) Uani 1 1 d . . . H3A H 0.2966 0.2433 0.1968 0.019 Uiso 1 1 calc R . . C4 C 0.35732(17) 0.17374(12) 0.09256(13) 0.0169(4) Uani 1 1 d . . . C5 C 0.26359(18) 0.16929(13) 0.03441(13) 0.0212(4) Uani 1 1 d . . . H5A H 0.1850 0.1658 0.0548 0.025 Uiso 1 1 calc R . . C6 C 0.28406(19) 0.16999(14) -0.05222(13) 0.0237(4) Uani 1 1 d . . . H6A H 0.2198 0.1659 -0.0906 0.028 Uiso 1 1 calc R . . C7 C 0.3983(2) 0.17672(13) -0.08296(12) 0.0239(4) Uani 1 1 d . . . H7A H 0.4125 0.1783 -0.1423 0.029 Uiso 1 1 calc R . . C8 C 0.49109(19) 0.18106(14) -0.02649(14) 0.0248(4) Uani 1 1 d . . . H8A H 0.5694 0.1853 -0.0474 0.030 Uiso 1 1 calc R . . C9 C 0.47123(18) 0.17930(13) 0.06127(13) 0.0203(4) Uani 1 1 d . . . H9A H 0.5359 0.1819 0.0994 0.024 Uiso 1 1 calc R . . C10 C 0.13139(16) 0.06270(13) 0.34299(12) 0.0191(4) Uani 1 1 d . . . H10A H 0.1604 0.0005 0.3329 0.023 Uiso 1 1 calc R . . H10B H 0.0592 0.0710 0.3087 0.023 Uiso 1 1 calc R . . C11 C 0.0995(2) 0.07224(14) 0.43640(12) 0.0234(4) Uani 1 1 d . . . H11A H 0.1717 0.0758 0.4703 0.035 Uiso 1 1 calc R . . H11B H 0.0532 0.0197 0.4543 0.035 Uiso 1 1 calc R . . H11C H 0.0531 0.1274 0.4446 0.035 Uiso 1 1 calc R . . C12 C 0.18634(17) 0.22373(13) 0.33188(13) 0.0193(4) Uani 1 1 d . . . H12A H 0.2510 0.2645 0.3142 0.023 Uiso 1 1 calc R . . H12B H 0.1773 0.2300 0.3941 0.023 Uiso 1 1 calc R . . C13 C 0.07305(18) 0.25590(14) 0.28990(14) 0.0248(4) Uani 1 1 d . . . H13A H 0.0808 0.2512 0.2282 0.037 Uiso 1 1 calc R . . H13B H 0.0582 0.3190 0.3055 0.037 Uiso 1 1 calc R . . H13C H 0.0072 0.2182 0.3090 0.037 Uiso 1 1 calc R . . C14 C 0.29427(16) 0.01766(12) 0.21056(12) 0.0155(3) Uani 1 1 d . . . C15 C 0.27069(16) -0.04370(11) 0.14657(13) 0.0187(3) Uani 1 1 d . . . H15A H 0.2139 -0.0305 0.1041 0.022 Uiso 1 1 calc R . . C16 C 0.33193(18) -0.12502(12) 0.14573(14) 0.0215(4) Uani 1 1 d . . . H16A H 0.3163 -0.1682 0.1026 0.026 Uiso 1 1 calc R . . C17 C 0.41607(19) -0.14384(12) 0.20754(12) 0.0199(4) Uani 1 1 d . . . H17A H 0.4591 -0.1989 0.2067 0.024 Uiso 1 1 calc R . . C18 C 0.43505(16) -0.07992(12) 0.27016(11) 0.0162(3) Uani 1 1 d . . . C19 C 0.52320(16) -0.09044(12) 0.34063(11) 0.0168(3) Uani 1 1 d . . . H19A H 0.5914 -0.1261 0.3203 0.020 Uiso 1 1 calc R . . H19B H 0.4868 -0.1234 0.3886 0.020 Uiso 1 1 calc R . . C20 C 0.70084(18) 0.04704(14) 0.30289(14) 0.0218(4) Uani 1 1 d . . . C21 C 0.65118(19) 0.03394(15) 0.21311(13) 0.0245(4) Uani 1 1 d . . . H21A H 0.7073 0.0577 0.1715 0.037 Uiso 1 1 calc R . . H21B H 0.5763 0.0664 0.2079 0.037 Uiso 1 1 calc R . . H21C H 0.6382 -0.0306 0.2026 0.037 Uiso 1 1 calc R . . C22 C 0.7357(2) 0.14700(15) 0.31079(17) 0.0301(5) Uani 1 1 d . . . H22A H 0.7768 0.1566 0.3647 0.045 Uiso 1 1 calc R . . H22B H 0.6648 0.1847 0.3090 0.045 Uiso 1 1 calc R . . H22C H 0.7878 0.1634 0.2637 0.045 Uiso 1 1 calc R . . C23 C 0.80977(19) -0.01357(15) 0.31200(15) 0.0270(4) Uani 1 1 d . . . H23A H 0.8645 -0.0014 0.2653 0.040 Uiso 1 1 calc R . . H23B H 0.7857 -0.0772 0.3103 0.040 Uiso 1 1 calc R . . H23C H 0.8487 -0.0009 0.3662 0.040 Uiso 1 1 calc R . . C24 C 0.63245(18) -0.00025(13) 0.48663(13) 0.0199(4) Uani 1 1 d . . . C25 C 0.7130(2) 0.07793(14) 0.51397(14) 0.0271(5) Uani 1 1 d . . . H25A H 0.6736 0.1357 0.5028 0.041 Uiso 1 1 calc R . . H25B H 0.7868 0.0752 0.4819 0.041 Uiso 1 1 calc R . . H25C H 0.7299 0.0728 0.5747 0.041 Uiso 1 1 calc R . . C26 C 0.69801(18) -0.09097(14) 0.49160(13) 0.0251(4) Uani 1 1 d . . . H26A H 0.7280 -0.0999 0.5493 0.038 Uiso 1 1 calc R . . H26B H 0.7640 -0.0907 0.4515 0.038 Uiso 1 1 calc R . . H26C H 0.6439 -0.1402 0.4772 0.038 Uiso 1 1 calc R . . C27 C 0.5291(2) -0.00464(15) 0.54910(13) 0.0255(4) Uani 1 1 d . . . H27A H 0.5586 -0.0202 0.6057 0.038 Uiso 1 1 calc R . . H27B H 0.4730 -0.0508 0.5303 0.038 Uiso 1 1 calc R . . H27C H 0.4898 0.0543 0.5512 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ru1 0.01333(6) 0.01260(6) 0.01568(6) -0.00216(5) -0.00163(5) 0.00058(5) P1 0.0140(2) 0.01378(19) 0.0165(2) -0.00139(15) -0.00160(16) 0.00081(16) O1 0.0417(10) 0.0265(8) 0.0317(8) -0.0139(7) -0.0090(7) 0.0030(7) O2 0.0153(6) 0.0172(6) 0.0211(6) 0.0021(5) -0.0046(5) -0.0031(5) N1 0.0153(7) 0.0138(7) 0.0177(7) -0.0011(6) -0.0001(6) 0.0010(6) N2 0.0149(7) 0.0131(7) 0.0160(7) -0.0012(6) -0.0005(6) -0.0012(5) C1 0.0192(9) 0.0176(8) 0.0240(9) -0.0014(7) -0.0030(7) 0.0028(7) C2 0.0142(7) 0.0156(8) 0.0161(8) 0.0008(7) -0.0022(6) -0.0001(7) C3 0.0163(8) 0.0117(8) 0.0200(9) -0.0002(7) -0.0014(7) 0.0004(7) C4 0.0187(8) 0.0113(8) 0.0207(9) 0.0012(7) -0.0007(7) 0.0004(7) C5 0.0189(9) 0.0224(9) 0.0222(9) 0.0019(8) 0.0006(7) -0.0039(8) C6 0.0245(10) 0.0265(10) 0.0202(10) 0.0004(8) -0.0028(8) -0.0043(8) C7 0.0302(10) 0.0206(9) 0.0209(9) 0.0011(7) 0.0035(9) -0.0020(9) C8 0.0232(10) 0.0223(10) 0.0290(11) 0.0022(8) 0.0072(8) 0.0015(8) C9 0.0177(9) 0.0174(9) 0.0258(10) 0.0030(8) -0.0006(8) 0.0007(7) C10 0.0160(8) 0.0201(8) 0.0213(10) 0.0010(7) 0.0005(7) -0.0031(7) C11 0.0227(9) 0.0264(9) 0.0212(9) 0.0013(7) 0.0041(9) 0.0020(8) C12 0.0194(9) 0.0168(8) 0.0219(9) -0.0028(7) -0.0007(7) 0.0045(7) C13 0.0208(10) 0.0215(9) 0.0320(11) 0.0004(8) -0.0013(8) 0.0068(8) C14 0.0156(8) 0.0152(8) 0.0156(8) 0.0020(7) -0.0006(7) -0.0027(7) C15 0.0220(8) 0.0173(8) 0.0170(8) 0.0015(8) -0.0054(8) -0.0019(7) C16 0.0304(9) 0.0164(8) 0.0179(8) -0.0035(7) -0.0049(9) -0.0010(7) C17 0.0242(9) 0.0149(8) 0.0205(8) -0.0020(6) -0.0040(8) 0.0015(8) C18 0.0185(8) 0.0141(8) 0.0161(8) 0.0009(6) -0.0007(6) -0.0003(6) C19 0.0160(7) 0.0153(8) 0.0190(8) -0.0007(7) -0.0035(6) 0.0022(6) C20 0.0162(9) 0.0221(10) 0.0270(10) 0.0002(8) 0.0021(8) 0.0018(7) C21 0.0219(10) 0.0287(11) 0.0230(10) 0.0028(8) 0.0062(8) 0.0043(8) C22 0.0273(11) 0.0217(10) 0.0414(13) 0.0022(9) 0.0079(10) -0.0048(9) C23 0.0175(9) 0.0287(11) 0.0347(12) -0.0019(9) 0.0026(8) 0.0027(8) C24 0.0225(9) 0.0169(8) 0.0201(9) -0.0030(7) -0.0065(7) 0.0031(7) C25 0.0292(11) 0.0240(10) 0.0282(10) -0.0043(8) -0.0115(9) 0.0007(8) C26 0.0277(10) 0.0217(10) 0.0257(10) -0.0011(8) -0.0093(8) 0.0064(8) C27 0.0302(11) 0.0292(11) 0.0173(9) 0.0015(8) -0.0008(8) 0.0032(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru1 H1 1.51(2) . ? Ru1 C1 1.8367(19) . ? Ru1 N2 2.0760(15) . ? Ru1 N1 2.2231(16) . ? Ru1 O2 2.2315(13) . ? Ru1 P1 2.2618(5) . ? P1 C19 1.8644(18) . ? P1 C24 1.885(2) . ? P1 C20 1.890(2) . ? O1 C1 1.163(2) . ? O2 C3 1.377(2) . ? N1 C10 1.496(2) . ? N1 C12 1.501(2) . ? N1 C2 1.509(2) . ? N2 C18 1.346(2) . ? N2 C14 1.346(2) . ? C2 C14 1.509(3) . ? C2 C3 1.558(3) . ? C3 C4 1.535(3) . ? C4 C9 1.387(3) . ? C4 C5 1.406(3) . ? C5 C6 1.386(3) . ? C6 C7 1.389(3) . ? C7 C8 1.381(3) . ? C8 C9 1.402(3) . ? C10 C11 1.523(3) . ? C12 C13 1.523(3) . ? C14 C15 1.383(3) . ? C15 C16 1.389(2) . ? C16 C17 1.393(3) . ? C17 C18 1.384(2) . ? C18 C19 1.504(2) . ? C20 C23 1.534(3) . ? C20 C22 1.535(3) . ? C20 C21 1.536(3) . ? C24 C27 1.533(3) . ? C24 C25 1.536(3) . ? C24 C26 1.536(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 H1 Ru1 C1 86.7(9) . . ? H1 Ru1 N2 89.0(9) . . ? C1 Ru1 N2 175.74(8) . . ? H1 Ru1 N1 92.7(9) . . ? C1 Ru1 N1 104.19(7) . . ? N2 Ru1 N1 76.64(6) . . ? H1 Ru1 O2 167.3(9) . . ? C1 Ru1 O2 102.94(7) . . ? N2 Ru1 O2 81.32(5) . . ? N1 Ru1 O2 77.03(5) . . ? H1 Ru1 P1 81.2(9) . . ? C1 Ru1 P1 97.13(6) . . ? N2 Ru1 P1 81.57(4) . . ? N1 Ru1 P1 157.48(4) . . ? O2 Ru1 P1 105.39(4) . . ? C19 P1 C24 103.08(8) . . ? C19 P1 C20 102.38(9) . . ? C24 P1 C20 109.39(9) . . ? C19 P1 Ru1 99.18(6) . . ? C24 P1 Ru1 121.37(6) . . ? C20 P1 Ru1 117.61(7) . . ? C3 O2 Ru1 112.27(11) . . ? C10 N1 C12 110.83(15) . . ? C10 N1 C2 107.69(14) . . ? C12 N1 C2 113.14(14) . . ? C10 N1 Ru1 115.66(11) . . ? C12 N1 Ru1 111.07(11) . . ? C2 N1 Ru1 97.86(10) . . ? C18 N2 C14 121.55(16) . . ? C18 N2 Ru1 123.51(12) . . ? C14 N2 Ru1 114.86(12) . . ? O1 C1 Ru1 175.76(18) . . ? N1 C2 C14 107.68(14) . . ? N1 C2 C3 107.30(14) . . ? C14 C2 C3 109.39(15) . . ? O2 C3 C4 114.17(16) . . ? O2 C3 C2 110.08(15) . . ? C4 C3 C2 111.98(16) . . ? C9 C4 C5 118.48(18) . . ? C9 C4 C3 120.64(17) . . ? C5 C4 C3 120.56(18) . . ? C6 C5 C4 121.02(19) . . ? C5 C6 C7 120.1(2) . . ? C8 C7 C6 119.42(19) . . ? C7 C8 C9 120.83(19) . . ? C4 C9 C8 120.14(19) . . ? N1 C10 C11 114.30(16) . . ? N1 C12 C13 116.04(16) . . ? N2 C14 C15 120.41(17) . . ? N2 C14 C2 113.03(15) . . ? C15 C14 C2 126.46(16) . . ? C14 C15 C16 118.55(18) . . ? C15 C16 C17 120.64(18) . . ? C18 C17 C16 118.02(17) . . ? N2 C18 C17 120.83(17) . . ? N2 C18 C19 115.08(15) . . ? C17 C18 C19 124.08(16) . . ? C18 C19 P1 109.84(12) . . ? C23 C20 C22 110.29(17) . . ? C23 C20 C21 107.98(17) . . ? C22 C20 C21 106.91(18) . . ? C23 C20 P1 116.61(15) . . ? C22 C20 P1 109.11(15) . . ? C21 C20 P1 105.42(13) . . ? C27 C24 C25 107.88(17) . . ? C27 C24 C26 107.52(17) . . ? C25 C24 C26 110.76(17) . . ? C27 C24 P1 109.08(14) . . ? C25 C24 P1 109.28(14) . . ? C26 C24 P1 112.19(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.61 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.645 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 936848'