# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_compound-2 #TrackingRef 'Compound-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C51 H47 B Cl N P2 Ru, C7 H8' _chemical_formula_sum 'C58 H55 B Cl N P2 Ru' _chemical_formula_weight 975.30 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' B B 0.0013 0.0007 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.1299(3) _cell_length_b 13.8383(3) _cell_length_c 27.1041(6) _cell_angle_alpha 79.247(2) _cell_angle_beta 84.900(2) _cell_angle_gamma 81.114(2) _cell_volume 4770.99(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18844 _cell_measurement_theta_min 2.7752 _cell_measurement_theta_max 29.0671 _exptl_crystal_description block _exptl_crystal_colour orange-red _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 0.492 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90491 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42377 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 26.00 _reflns_number_total 18722 _reflns_number_gt 12643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0401P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 18722 _refine_ls_number_parameters 1153 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0822 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 1.010 _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 0.103693(15) 0.028768(14) 0.132659(7) 0.01445(6) Uani 1 1 d . . . P1 P -0.02558(5) -0.00158(5) 0.19315(2) 0.01596(15) Uani 1 1 d . . . P2 P 0.09452(5) 0.20218(5) 0.12474(2) 0.01602(15) Uani 1 1 d . . . Cl1 Cl 0.23371(5) 0.00074(5) 0.19527(2) 0.02401(15) Uani 1 1 d . . . B1 B 0.1126(2) 0.0395(2) 0.04462(11) 0.0206(7) Uani 1 1 d . . . N1 N 0.20492(16) -0.02384(15) 0.06731(8) 0.0204(5) Uani 1 1 d . . . C11 C 0.0212(2) -0.00785(18) 0.07093(9) 0.0201(6) Uani 1 1 d . . . H11A H -0.0531 0.0143 0.0639 0.024 Uiso 1 1 calc R . . C12 C 0.0621(2) -0.09662(19) 0.10300(9) 0.0228(6) Uani 1 1 d . . . H12A H 0.0203 -0.1476 0.1222 0.027 Uiso 1 1 calc R . . C13 C 0.1689(2) -0.10294(18) 0.10283(9) 0.0222(6) Uani 1 1 d . . . H13A H 0.2148 -0.1601 0.1214 0.027 Uiso 1 1 calc R . . C14 C 0.3168(2) -0.0374(2) 0.04851(10) 0.0263(6) Uani 1 1 d . . . C15 C 0.3315(2) -0.1255(2) 0.02047(11) 0.0371(8) Uani 1 1 d . . . H15A H 0.2854 -0.1110 -0.0073 0.056 Uiso 1 1 calc R . . H15B H 0.3153 -0.1851 0.0437 0.056 Uiso 1 1 calc R . . H15C H 0.4034 -0.1366 0.0070 0.056 Uiso 1 1 calc R . . C16 C 0.3874(2) -0.0587(2) 0.09232(11) 0.0355(7) Uani 1 1 d . . . H16A H 0.3769 -0.0018 0.1099 0.053 Uiso 1 1 calc R . . H16B H 0.4596 -0.0698 0.0794 0.053 Uiso 1 1 calc R . . H16C H 0.3709 -0.1180 0.1157 0.053 Uiso 1 1 calc R . . C17 C 0.3415(2) 0.0553(2) 0.01264(11) 0.0323(7) Uani 1 1 d . . . H17A H 0.2964 0.0690 -0.0155 0.048 Uiso 1 1 calc R . . H17B H 0.4138 0.0451 -0.0002 0.048 Uiso 1 1 calc R . . H17C H 0.3303 0.1118 0.0305 0.048 Uiso 1 1 calc R . . C18 C 0.1122(2) 0.12776(19) 0.00116(10) 0.0220(6) Uani 1 1 d . . . C19 C 0.1051(2) 0.1944(2) -0.03431(10) 0.0241(6) Uani 1 1 d . . . C101 C 0.1041(2) 0.27179(19) -0.07794(10) 0.0238(6) Uani 1 1 d . . . C102 C 0.0125(2) 0.3217(2) -0.09776(11) 0.0324(7) Uani 1 1 d . . . H10A H -0.0519 0.3076 -0.0814 0.039 Uiso 1 1 calc R . . C103 C 0.0152(3) 0.3924(2) -0.14157(12) 0.0409(8) Uani 1 1 d . . . H10B H -0.0475 0.4260 -0.1552 0.049 Uiso 1 1 calc R . . C104 C 0.1077(3) 0.4137(2) -0.16520(12) 0.0438(9) Uani 1 1 d . . . H10C H 0.1089 0.4614 -0.1953 0.053 Uiso 1 1 calc R . . C105 C 0.1984(3) 0.3667(2) -0.14556(12) 0.0433(9) Uani 1 1 d . . . H10D H 0.2625 0.3823 -0.1617 0.052 Uiso 1 1 calc R . . C106 C 0.1966(2) 0.2959(2) -0.10186(11) 0.0327(7) Uani 1 1 d . . . H10E H 0.2598 0.2636 -0.0882 0.039 Uiso 1 1 calc R . . C111 C -0.0135(2) -0.13271(18) 0.22560(9) 0.0194(6) Uani 1 1 d . . . C112 C -0.0985(2) -0.1703(2) 0.25320(10) 0.0276(6) Uani 1 1 d . . . H11B H -0.1629 -0.1286 0.2548 0.033 Uiso 1 1 calc R . . C113 C -0.0894(3) -0.2682(2) 0.27827(11) 0.0380(8) Uani 1 1 d . . . H11C H -0.1477 -0.2936 0.2963 0.046 Uiso 1 1 calc R . . C114 C 0.0042(3) -0.3279(2) 0.27688(11) 0.0379(8) Uani 1 1 d . . . H11D H 0.0103 -0.3949 0.2939 0.045 Uiso 1 1 calc R . . C115 C 0.0894(2) -0.2916(2) 0.25101(11) 0.0340(7) Uani 1 1 d . . . H11E H 0.1542 -0.3330 0.2509 0.041 Uiso 1 1 calc R . . C116 C 0.0802(2) -0.19408(19) 0.22506(10) 0.0239(6) Uani 1 1 d . . . H11F H 0.1389 -0.1695 0.2068 0.029 Uiso 1 1 calc R . . C121 C -0.15222(19) 0.01544(18) 0.16633(9) 0.0176(6) Uani 1 1 d . . . C122 C -0.1901(2) -0.06199(19) 0.15105(10) 0.0225(6) Uani 1 1 d . . . H12B H -0.1522 -0.1269 0.1566 0.027 Uiso 1 1 calc R . . C123 C -0.2827(2) -0.0457(2) 0.12774(10) 0.0263(6) Uani 1 1 d . . . H12C H -0.3075 -0.0995 0.1176 0.032 Uiso 1 1 calc R . . C124 C -0.3386(2) 0.0472(2) 0.11922(10) 0.0281(7) Uani 1 1 d . . . H12D H -0.4023 0.0579 0.1035 0.034 Uiso 1 1 calc R . . C125 C -0.3017(2) 0.1258(2) 0.13359(11) 0.0292(7) Uani 1 1 d . . . H12E H -0.3399 0.1906 0.1276 0.035 Uiso 1 1 calc R . . C126 C -0.2095(2) 0.11002(19) 0.15661(10) 0.0235(6) Uani 1 1 d . . . H12F H -0.1846 0.1644 0.1660 0.028 Uiso 1 1 calc R . . C131 C -0.0531(2) 0.05576(18) 0.25000(9) 0.0203(6) Uani 1 1 d . . . C132 C -0.1514(2) 0.0702(2) 0.27322(10) 0.0291(7) Uani 1 1 d . . . H13B H -0.2089 0.0589 0.2572 0.035 Uiso 1 1 calc R . . C133 C -0.1669(3) 0.1010(2) 0.31946(11) 0.0373(8) Uani 1 1 d . . . H13C H -0.2347 0.1112 0.3348 0.045 Uiso 1 1 calc R . . C134 C -0.0840(3) 0.1167(2) 0.34308(11) 0.0380(8) Uani 1 1 d . . . H13D H -0.0942 0.1364 0.3751 0.046 Uiso 1 1 calc R . . C135 C 0.0139(3) 0.1037(2) 0.32025(11) 0.0353(7) Uani 1 1 d . . . H13E H 0.0708 0.1158 0.3364 0.042 Uiso 1 1 calc R . . C136 C 0.0302(2) 0.07326(19) 0.27398(10) 0.0265(6) Uani 1 1 d . . . H13F H 0.0980 0.0643 0.2586 0.032 Uiso 1 1 calc R . . C211 C 0.08012(19) 0.26722(18) 0.17934(9) 0.0190(6) Uani 1 1 d . . . C212 C -0.0174(2) 0.28150(19) 0.20322(10) 0.0253(6) Uani 1 1 d . . . H21A H -0.0723 0.2553 0.1921 0.030 Uiso 1 1 calc R . . C213 C -0.0366(2) 0.3332(2) 0.24309(10) 0.0315(7) Uani 1 1 d . . . H21B H -0.1040 0.3418 0.2591 0.038 Uiso 1 1 calc R . . C214 C 0.0425(3) 0.3720(2) 0.25936(11) 0.0354(8) Uani 1 1 d . . . H21C H 0.0299 0.4075 0.2866 0.042 Uiso 1 1 calc R . . C215 C 0.1392(3) 0.3592(2) 0.23598(12) 0.0402(8) Uani 1 1 d . . . H21D H 0.1935 0.3864 0.2471 0.048 Uiso 1 1 calc R . . C216 C 0.1590(2) 0.3070(2) 0.19626(11) 0.0307(7) Uani 1 1 d . . . H21E H 0.2266 0.2984 0.1806 0.037 Uiso 1 1 calc R . . C221 C -0.00563(19) 0.28439(19) 0.08804(9) 0.0194(6) Uani 1 1 d . . . C222 C -0.0771(2) 0.2466(2) 0.06490(10) 0.0243(6) Uani 1 1 d . . . H22A H -0.0748 0.1767 0.0680 0.029 Uiso 1 1 calc R . . C223 C -0.1522(2) 0.3110(2) 0.03702(12) 0.0392(8) Uani 1 1 d . . . H22B H -0.2005 0.2847 0.0209 0.047 Uiso 1 1 calc R . . C224 C -0.1570(2) 0.4114(2) 0.03271(12) 0.0412(8) Uani 1 1 d . . . H22C H -0.2082 0.4547 0.0136 0.049 Uiso 1 1 calc R . . C225 C -0.0875(2) 0.4502(2) 0.05606(11) 0.0353(7) Uani 1 1 d . . . H22D H -0.0911 0.5201 0.0531 0.042 Uiso 1 1 calc R . . C226 C -0.0131(2) 0.38762(19) 0.08364(10) 0.0261(6) Uani 1 1 d . . . H22E H 0.0339 0.4149 0.1000 0.031 Uiso 1 1 calc R . . C231 C 0.21459(19) 0.24118(18) 0.09186(10) 0.0196(6) Uani 1 1 d . . . C232 C 0.2181(2) 0.30095(18) 0.04457(10) 0.0242(6) Uani 1 1 d . . . H23A H 0.1560 0.3255 0.0281 0.029 Uiso 1 1 calc R . . C233 C 0.3111(2) 0.3251(2) 0.02118(12) 0.0344(7) Uani 1 1 d . . . H23B H 0.3121 0.3655 -0.0112 0.041 Uiso 1 1 calc R . . C234 C 0.4020(2) 0.2912(2) 0.04432(12) 0.0379(8) Uani 1 1 d . . . H23C H 0.4656 0.3081 0.0281 0.045 Uiso 1 1 calc R . . C235 C 0.3998(2) 0.2317(2) 0.09192(12) 0.0358(8) Uani 1 1 d . . . H23D H 0.4620 0.2094 0.1086 0.043 Uiso 1 1 calc R . . C236 C 0.3073(2) 0.20521(19) 0.11479(11) 0.0262(6) Uani 1 1 d . . . H23E H 0.3068 0.1620 0.1465 0.031 Uiso 1 1 calc R . . Ru2 Ru 0.407326(15) 0.474031(14) 0.364844(7) 0.01432(6) Uani 1 1 d . . . P3 P 0.41970(5) 0.30087(5) 0.37170(2) 0.01584(15) Uani 1 1 d . . . P4 P 0.54251(5) 0.50458(5) 0.30766(2) 0.01621(15) Uani 1 1 d . . . Cl2 Cl 0.28432(5) 0.50355(5) 0.29890(2) 0.02322(15) Uani 1 1 d . . . B2 B 0.3885(2) 0.4617(2) 0.45293(11) 0.0194(7) Uani 1 1 d . . . N2 N 0.29786(16) 0.52513(15) 0.42840(8) 0.0193(5) Uani 1 1 d . . . C21 C 0.4812(2) 0.51030(19) 0.42955(9) 0.0207(6) Uani 1 1 d . . . H21F H 0.5545 0.4887 0.4385 0.025 Uiso 1 1 calc R . . C22 C 0.4424(2) 0.59948(19) 0.39689(10) 0.0220(6) Uani 1 1 d . . . H22F H 0.4848 0.6512 0.3792 0.026 Uiso 1 1 calc R . . C23 C 0.3365(2) 0.60438(18) 0.39410(9) 0.0220(6) Uani 1 1 d . . . H23F H 0.2920 0.6614 0.3746 0.026 Uiso 1 1 calc R . . C24 C 0.1849(2) 0.53752(19) 0.44481(10) 0.0238(6) Uani 1 1 d . . . C25 C 0.1674(2) 0.6233(2) 0.47490(11) 0.0348(7) Uani 1 1 d . . . H25A H 0.2111 0.6064 0.5036 0.052 Uiso 1 1 calc R . . H25B H 0.0947 0.6340 0.4870 0.052 Uiso 1 1 calc R . . H25C H 0.1854 0.6840 0.4532 0.052 Uiso 1 1 calc R . . C26 C 0.1570(2) 0.4432(2) 0.47851(11) 0.0305(7) Uani 1 1 d . . . H26A H 0.1994 0.4273 0.5077 0.046 Uiso 1 1 calc R . . H26B H 0.1698 0.3883 0.4596 0.046 Uiso 1 1 calc R . . H26C H 0.0838 0.4534 0.4900 0.046 Uiso 1 1 calc R . . C27 C 0.1183(2) 0.5618(2) 0.39985(11) 0.0313(7) Uani 1 1 d . . . H27A H 0.1304 0.5065 0.3812 0.047 Uiso 1 1 calc R . . H27B H 0.1364 0.6222 0.3778 0.047 Uiso 1 1 calc R . . H27C H 0.0454 0.5726 0.4115 0.047 Uiso 1 1 calc R . . C28 C 0.3845(2) 0.37226(19) 0.49573(10) 0.0214(6) Uani 1 1 d . . . C29 C 0.3852(2) 0.3056(2) 0.53081(10) 0.0249(6) Uani 1 1 d . . . C201 C 0.3762(2) 0.22764(19) 0.57377(10) 0.0230(6) Uani 1 1 d . . . C202 C 0.2786(2) 0.2036(2) 0.59211(11) 0.0314(7) Uani 1 1 d . . . H20A H 0.2192 0.2364 0.5751 0.038 Uiso 1 1 calc R . . C203 C 0.2677(3) 0.1323(2) 0.63467(12) 0.0406(8) Uani 1 1 d . . . H20B H 0.2011 0.1164 0.6468 0.049 Uiso 1 1 calc R . . C204 C 0.3536(3) 0.0847(2) 0.65932(12) 0.0441(9) Uani 1 1 d . . . H20C H 0.3458 0.0368 0.6890 0.053 Uiso 1 1 calc R . . C205 C 0.4501(3) 0.1056(2) 0.64160(11) 0.0409(8) Uani 1 1 d . . . H20D H 0.5088 0.0715 0.6588 0.049 Uiso 1 1 calc R . . C206 C 0.4631(2) 0.1765(2) 0.59860(11) 0.0318(7) Uani 1 1 d . . . H20E H 0.5303 0.1900 0.5862 0.038 Uiso 1 1 calc R . . C311 C 0.29824(19) 0.25947(18) 0.40115(10) 0.0188(6) Uani 1 1 d . . . C312 C 0.2077(2) 0.29763(19) 0.37643(10) 0.0234(6) Uani 1 1 d . . . H31A H 0.2105 0.3444 0.3460 0.028 Uiso 1 1 calc R . . C313 C 0.1138(2) 0.2679(2) 0.39581(11) 0.0309(7) Uani 1 1 d . . . H31B H 0.0533 0.2921 0.3780 0.037 Uiso 1 1 calc R . . C314 C 0.1085(2) 0.2029(2) 0.44115(12) 0.0368(8) Uani 1 1 d . . . H31C H 0.0444 0.1825 0.4546 0.044 Uiso 1 1 calc R . . C315 C 0.1963(2) 0.1682(2) 0.46665(11) 0.0329(7) Uani 1 1 d . . . H31D H 0.1921 0.1251 0.4982 0.040 Uiso 1 1 calc R . . C316 C 0.2914(2) 0.19527(19) 0.44690(10) 0.0245(6) Uani 1 1 d . . . H31E H 0.3517 0.1698 0.4647 0.029 Uiso 1 1 calc R . . C321 C 0.51812(19) 0.21986(18) 0.41058(9) 0.0193(6) Uani 1 1 d . . . C322 C 0.5271(2) 0.1167(2) 0.41542(10) 0.0281(7) Uani 1 1 d . . . H32A H 0.4831 0.0883 0.3979 0.034 Uiso 1 1 calc R . . C323 C 0.5993(2) 0.0555(2) 0.44536(12) 0.0385(8) Uani 1 1 d . . . H32B H 0.6043 -0.0146 0.4487 0.046 Uiso 1 1 calc R . . C324 C 0.6639(3) 0.0966(2) 0.47031(12) 0.0465(9) Uani 1 1 d . . . H32C H 0.7134 0.0546 0.4911 0.056 Uiso 1 1 calc R . . C325 C 0.6572(3) 0.1975(2) 0.46541(13) 0.0436(9) Uani 1 1 d . . . H32D H 0.7028 0.2252 0.4824 0.052 Uiso 1 1 calc R . . C326 C 0.5843(2) 0.2597(2) 0.43578(10) 0.0275(7) Uani 1 1 d . . . H32E H 0.5797 0.3297 0.4328 0.033 Uiso 1 1 calc R . . C331 C 0.43986(19) 0.23627(18) 0.31702(9) 0.0185(6) Uani 1 1 d . . . C332 C 0.5399(2) 0.21979(19) 0.29569(10) 0.0241(6) Uani 1 1 d . . . H33A H 0.5941 0.2432 0.3090 0.029 Uiso 1 1 calc R . . C333 C 0.5621(2) 0.1700(2) 0.25541(10) 0.0299(7) Uani 1 1 d . . . H33B H 0.6309 0.1603 0.2412 0.036 Uiso 1 1 calc R . . C334 C 0.4846(2) 0.1342(2) 0.23579(11) 0.0340(7) Uani 1 1 d . . . H33C H 0.4996 0.1000 0.2081 0.041 Uiso 1 1 calc R . . C335 C 0.3855(2) 0.1488(2) 0.25692(11) 0.0379(8) Uani 1 1 d . . . H33D H 0.3320 0.1237 0.2440 0.046 Uiso 1 1 calc R . . C336 C 0.3629(2) 0.1997(2) 0.29678(11) 0.0305(7) Uani 1 1 d . . . H33E H 0.2938 0.2099 0.3106 0.037 Uiso 1 1 calc R . . C411 C 0.5751(2) 0.44900(18) 0.25048(9) 0.0204(6) Uani 1 1 d . . . C412 C 0.6754(2) 0.4362(2) 0.22883(10) 0.0293(7) Uani 1 1 d . . . H41A H 0.7309 0.4481 0.2460 0.035 Uiso 1 1 calc R . . C413 C 0.6949(3) 0.4061(2) 0.18231(11) 0.0380(8) Uani 1 1 d . . . H41B H 0.7636 0.3971 0.1679 0.046 Uiso 1 1 calc R . . C414 C 0.6137(3) 0.3894(2) 0.15707(11) 0.0374(8) Uani 1 1 d . . . H41C H 0.6267 0.3701 0.1250 0.045 Uiso 1 1 calc R . . C415 C 0.5150(3) 0.4007(2) 0.17830(11) 0.0343(7) Uani 1 1 d . . . H41D H 0.4599 0.3882 0.1610 0.041 Uiso 1 1 calc R . . C416 C 0.4947(2) 0.42997(19) 0.22468(10) 0.0266(6) Uani 1 1 d . . . H41E H 0.4259 0.4372 0.2391 0.032 Uiso 1 1 calc R . . C421 C 0.66650(19) 0.48538(19) 0.33743(9) 0.0188(6) Uani 1 1 d . . . C422 C 0.7252(2) 0.3917(2) 0.34423(10) 0.0265(7) Uani 1 1 d . . . H42A H 0.7022 0.3389 0.3323 0.032 Uiso 1 1 calc R . . C423 C 0.8171(2) 0.3745(2) 0.36818(11) 0.0324(7) Uani 1 1 d . . . H42B H 0.8564 0.3101 0.3725 0.039 Uiso 1 1 calc R . . C424 C 0.8518(2) 0.4501(2) 0.38576(10) 0.0288(7) Uani 1 1 d . . . H42C H 0.9150 0.4385 0.4019 0.035 Uiso 1 1 calc R . . C425 C 0.7937(2) 0.5424(2) 0.37969(10) 0.0272(7) Uani 1 1 d . . . H42D H 0.8168 0.5948 0.3919 0.033 Uiso 1 1 calc R . . C426 C 0.7020(2) 0.5599(2) 0.35602(10) 0.0246(6) Uani 1 1 d . . . H42E H 0.6627 0.6242 0.3524 0.030 Uiso 1 1 calc R . . C431 C 0.5340(2) 0.63641(18) 0.27630(9) 0.0196(6) Uani 1 1 d . . . C432 C 0.6224(2) 0.6758(2) 0.25402(10) 0.0292(7) Uani 1 1 d . . . H43A H 0.6878 0.6353 0.2555 0.035 Uiso 1 1 calc R . . C433 C 0.6147(3) 0.7740(2) 0.22982(11) 0.0392(8) Uani 1 1 d . . . H43B H 0.6753 0.8011 0.2159 0.047 Uiso 1 1 calc R . . C434 C 0.5204(3) 0.8326(2) 0.22581(11) 0.0399(8) Uani 1 1 d . . . H43C H 0.5157 0.8994 0.2086 0.048 Uiso 1 1 calc R . . C435 C 0.4326(2) 0.7943(2) 0.24684(11) 0.0342(7) Uani 1 1 d . . . H43D H 0.3672 0.8346 0.2440 0.041 Uiso 1 1 calc R . . C436 C 0.4394(2) 0.6960(2) 0.27240(10) 0.0266(7) Uani 1 1 d . . . H43E H 0.3787 0.6702 0.2872 0.032 Uiso 1 1 calc R . . C1S C 0.4375(3) 0.6341(2) 0.11411(15) 0.0499(10) Uani 1 1 d . . . C2S C 0.4310(3) 0.5871(3) 0.07409(13) 0.0542(10) Uani 1 1 d . . . H2SA H 0.4868 0.5851 0.0493 0.065 Uiso 1 1 calc R . . C3S C 0.3492(4) 0.5443(3) 0.06902(18) 0.0736(13) Uani 1 1 d . . . H3SA H 0.3467 0.5137 0.0406 0.088 Uiso 1 1 calc R . . C4S C 0.2676(4) 0.5443(3) 0.1052(2) 0.0852(15) Uani 1 1 d . . . H4SA H 0.2098 0.5127 0.1022 0.102 Uiso 1 1 calc R . . C5S C 0.2715(3) 0.5901(4) 0.14489(18) 0.0842(15) Uani 1 1 d . . . H5SA H 0.2154 0.5905 0.1695 0.101 Uiso 1 1 calc R . . C6S C 0.3543(3) 0.6359(3) 0.15051(16) 0.0621(11) Uani 1 1 d . . . H6SA H 0.3554 0.6681 0.1784 0.075 Uiso 1 1 calc R . . C7S C 0.5286(3) 0.6772(3) 0.1211(2) 0.0909(16) Uani 1 1 d . . . H7SA H 0.5794 0.6700 0.0928 0.136 Uiso 1 1 calc R . . H7SB H 0.5589 0.6427 0.1525 0.136 Uiso 1 1 calc R . . H7SC H 0.5088 0.7478 0.1227 0.136 Uiso 1 1 calc R . . C8S C 0.0862(4) 0.8849(4) 0.4022(2) 0.0989(17) Uani 1 1 d U . . C9S C 0.1063(4) 0.8493(3) 0.35618(15) 0.0645(12) Uani 1 1 d . . . H9SA H 0.0590 0.8141 0.3448 0.077 Uiso 1 1 calc R . . C10S C 0.1941(5) 0.8668(4) 0.3291(2) 0.1023(17) Uani 1 1 d . . . H10F H 0.2081 0.8422 0.2984 0.123 Uiso 1 1 calc R . . C11S C 0.2664(4) 0.9189(4) 0.34337(19) 0.0927(16) Uani 1 1 d . . . H11G H 0.3274 0.9304 0.3229 0.111 Uiso 1 1 calc R . . C12S C 0.2465(5) 0.9519(4) 0.3866(2) 0.1066(18) Uani 1 1 d U . . H12G H 0.2947 0.9869 0.3975 0.128 Uiso 1 1 calc R . . C13S C 0.1540(4) 0.9357(3) 0.41739(18) 0.0718(13) Uani 1 1 d . . . H13G H 0.1405 0.9605 0.4481 0.086 Uiso 1 1 calc R . . C14S C -0.0078(4) 0.8689(4) 0.4269(2) 0.129(2) Uani 1 1 d U . . H14A H -0.0153 0.8963 0.4581 0.193 Uiso 1 1 calc R . . H14B H -0.0112 0.7974 0.4349 0.193 Uiso 1 1 calc R . . H14C H -0.0635 0.9017 0.4053 0.193 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 0.01648(11) 0.01213(12) 0.01474(11) -0.00194(9) -0.00197(8) -0.00192(8) P1 0.0178(3) 0.0136(4) 0.0158(3) -0.0010(3) -0.0023(3) -0.0016(3) P2 0.0174(3) 0.0142(4) 0.0170(4) -0.0029(3) -0.0034(3) -0.0022(3) Cl1 0.0226(3) 0.0262(4) 0.0231(4) -0.0022(3) -0.0081(3) -0.0016(3) B1 0.0272(17) 0.0184(17) 0.0180(16) -0.0082(13) -0.0014(13) -0.0025(13) N1 0.0246(12) 0.0179(13) 0.0182(12) -0.0033(10) 0.0036(9) -0.0044(10) C11 0.0262(14) 0.0207(15) 0.0169(14) -0.0087(12) -0.0033(11) -0.0068(12) C12 0.0373(16) 0.0173(15) 0.0172(14) -0.0078(12) 0.0009(12) -0.0101(13) C13 0.0329(16) 0.0142(15) 0.0183(14) -0.0040(11) 0.0021(11) -0.0008(12) C14 0.0245(15) 0.0256(17) 0.0252(15) -0.0039(13) 0.0062(12) 0.0025(12) C15 0.0433(19) 0.0300(18) 0.0364(18) -0.0140(15) 0.0137(14) 0.0008(14) C16 0.0228(15) 0.043(2) 0.0375(18) -0.0067(15) 0.0048(13) 0.0017(14) C17 0.0265(16) 0.0294(17) 0.0366(17) -0.0024(14) 0.0115(13) -0.0024(13) C18 0.0258(15) 0.0201(15) 0.0218(15) -0.0062(12) -0.0016(11) -0.0055(12) C19 0.0298(15) 0.0240(16) 0.0211(15) -0.0071(13) -0.0018(12) -0.0072(12) C101 0.0382(16) 0.0146(15) 0.0197(14) -0.0042(11) 0.0001(12) -0.0068(12) C102 0.0389(18) 0.0238(17) 0.0356(18) -0.0029(14) -0.0078(14) -0.0074(13) C103 0.051(2) 0.0302(18) 0.040(2) 0.0026(15) -0.0199(16) -0.0034(15) C104 0.071(3) 0.0278(18) 0.0268(17) 0.0082(14) -0.0038(16) -0.0048(17) C105 0.055(2) 0.0316(19) 0.0354(19) 0.0058(15) 0.0167(16) -0.0076(16) C106 0.0432(18) 0.0203(16) 0.0312(17) -0.0031(13) 0.0025(14) 0.0015(13) C111 0.0284(15) 0.0137(14) 0.0159(13) 0.0007(11) -0.0042(11) -0.0047(11) C112 0.0329(16) 0.0237(16) 0.0235(15) 0.0018(12) -0.0005(12) -0.0042(13) C113 0.050(2) 0.0292(18) 0.0326(18) 0.0100(14) -0.0031(15) -0.0174(16) C114 0.065(2) 0.0166(16) 0.0300(17) 0.0050(13) -0.0091(16) -0.0078(16) C115 0.0474(19) 0.0203(16) 0.0321(18) -0.0032(13) -0.0144(14) 0.0070(14) C116 0.0294(15) 0.0177(15) 0.0218(15) 0.0002(12) -0.0037(11) 0.0012(12) C121 0.0176(13) 0.0184(14) 0.0158(13) 0.0004(11) 0.0006(10) -0.0042(11) C122 0.0238(14) 0.0180(15) 0.0248(15) -0.0021(12) -0.0041(11) -0.0004(11) C123 0.0277(15) 0.0257(16) 0.0272(16) -0.0053(13) -0.0064(12) -0.0057(13) C124 0.0195(14) 0.0380(18) 0.0278(16) -0.0055(13) -0.0060(11) -0.0055(13) C125 0.0248(15) 0.0247(16) 0.0367(17) -0.0052(13) -0.0053(13) 0.0030(12) C126 0.0232(14) 0.0197(15) 0.0286(16) -0.0054(12) -0.0025(11) -0.0037(12) C131 0.0275(14) 0.0128(14) 0.0187(14) -0.0006(11) -0.0021(11) 0.0006(11) C132 0.0359(17) 0.0270(16) 0.0231(15) -0.0048(13) 0.0016(12) -0.0024(13) C133 0.049(2) 0.0307(18) 0.0290(17) -0.0100(14) 0.0116(14) 0.0021(15) C134 0.068(2) 0.0233(17) 0.0208(16) -0.0084(13) -0.0054(15) 0.0055(15) C135 0.051(2) 0.0263(17) 0.0295(17) -0.0054(14) -0.0170(15) 0.0001(14) C136 0.0309(16) 0.0207(15) 0.0268(16) -0.0047(12) -0.0058(12) 0.0021(12) C211 0.0247(14) 0.0136(14) 0.0174(14) -0.0009(11) -0.0047(11) 0.0010(11) C212 0.0334(16) 0.0191(15) 0.0240(15) -0.0036(12) -0.0053(12) -0.0043(12) C213 0.0396(18) 0.0259(17) 0.0240(16) -0.0031(13) 0.0006(13) 0.0078(13) C214 0.061(2) 0.0245(17) 0.0209(16) -0.0093(13) -0.0135(15) 0.0062(15) C215 0.047(2) 0.041(2) 0.0392(19) -0.0169(16) -0.0159(16) -0.0090(16) C216 0.0277(16) 0.0359(18) 0.0329(17) -0.0138(14) -0.0074(13) -0.0054(13) C221 0.0201(13) 0.0195(15) 0.0174(14) -0.0011(11) -0.0025(10) -0.0012(11) C222 0.0263(15) 0.0212(16) 0.0251(15) -0.0036(12) -0.0060(12) -0.0009(12) C223 0.0356(18) 0.041(2) 0.043(2) -0.0091(16) -0.0235(15) 0.0025(15) C224 0.045(2) 0.0317(19) 0.042(2) -0.0029(15) -0.0218(16) 0.0150(15) C225 0.0471(19) 0.0189(17) 0.0378(19) -0.0035(14) -0.0109(15) 0.0048(14) C226 0.0314(16) 0.0175(15) 0.0285(16) -0.0015(12) -0.0085(12) 0.0003(12) C231 0.0209(13) 0.0143(14) 0.0250(15) -0.0074(11) 0.0015(11) -0.0039(11) C232 0.0291(15) 0.0160(14) 0.0276(15) -0.0025(12) -0.0019(12) -0.0054(12) C233 0.0397(18) 0.0249(17) 0.0362(18) -0.0008(14) 0.0093(14) -0.0090(14) C234 0.0293(17) 0.0297(18) 0.052(2) -0.0023(15) 0.0117(14) -0.0098(14) C235 0.0202(15) 0.0336(18) 0.054(2) -0.0089(16) -0.0020(14) -0.0025(13) C236 0.0263(15) 0.0225(16) 0.0300(16) -0.0052(12) -0.0022(12) -0.0032(12) Ru2 0.01628(11) 0.01244(12) 0.01441(11) -0.00192(9) -0.00208(8) -0.00242(9) P3 0.0169(3) 0.0138(4) 0.0175(4) -0.0029(3) -0.0034(3) -0.0027(3) P4 0.0182(3) 0.0133(4) 0.0164(3) -0.0012(3) -0.0018(3) -0.0015(3) Cl2 0.0230(3) 0.0255(4) 0.0213(3) -0.0028(3) -0.0082(3) -0.0012(3) B2 0.0255(16) 0.0183(17) 0.0164(16) -0.0047(13) -0.0026(12) -0.0069(13) N2 0.0219(12) 0.0156(12) 0.0200(12) -0.0030(9) 0.0020(9) -0.0036(9) C21 0.0227(14) 0.0228(16) 0.0187(14) -0.0059(12) -0.0026(11) -0.0066(12) C22 0.0285(15) 0.0165(15) 0.0241(15) -0.0076(12) 0.0017(11) -0.0096(12) C23 0.0328(16) 0.0125(14) 0.0197(14) -0.0025(11) 0.0022(11) -0.0027(12) C24 0.0239(15) 0.0206(15) 0.0250(15) -0.0054(12) 0.0054(11) 0.0006(12) C25 0.0373(18) 0.0303(18) 0.0365(18) -0.0141(14) 0.0092(14) -0.0004(14) C26 0.0255(15) 0.0305(17) 0.0344(17) -0.0065(13) 0.0096(12) -0.0054(13) C27 0.0224(15) 0.0361(18) 0.0339(17) -0.0054(14) -0.0023(12) 0.0004(13) C28 0.0260(15) 0.0222(16) 0.0179(14) -0.0062(12) -0.0015(11) -0.0059(12) C29 0.0320(16) 0.0233(16) 0.0218(15) -0.0089(13) -0.0017(12) -0.0052(13) C201 0.0365(16) 0.0143(14) 0.0192(14) -0.0050(11) -0.0004(12) -0.0051(12) C202 0.0389(18) 0.0244(16) 0.0280(16) -0.0013(13) 0.0011(13) -0.0009(13) C203 0.049(2) 0.0308(18) 0.0355(18) 0.0030(14) 0.0133(15) -0.0050(15) C204 0.070(3) 0.0334(19) 0.0256(17) 0.0081(14) -0.0018(16) -0.0135(18) C205 0.058(2) 0.0303(18) 0.0326(18) 0.0029(15) -0.0167(16) -0.0033(16) C206 0.0407(18) 0.0266(17) 0.0301(17) -0.0042(14) -0.0055(13) -0.0096(14) C311 0.0197(13) 0.0161(14) 0.0224(14) -0.0082(11) 0.0005(11) -0.0032(11) C312 0.0240(14) 0.0224(15) 0.0247(15) -0.0052(12) -0.0028(11) -0.0041(12) C313 0.0246(15) 0.0315(17) 0.0386(18) -0.0093(14) -0.0036(13) -0.0053(13) C314 0.0304(17) 0.0367(19) 0.045(2) -0.0071(15) 0.0056(14) -0.0146(14) C315 0.0393(18) 0.0272(17) 0.0318(17) -0.0007(13) 0.0073(13) -0.0140(14) C316 0.0276(15) 0.0195(15) 0.0272(15) -0.0058(12) -0.0008(12) -0.0048(12) C321 0.0214(14) 0.0171(15) 0.0179(14) -0.0022(11) -0.0014(11) 0.0003(11) C322 0.0333(16) 0.0221(16) 0.0298(17) -0.0057(13) -0.0079(13) -0.0022(13) C323 0.050(2) 0.0212(17) 0.041(2) -0.0016(14) -0.0178(16) 0.0096(14) C324 0.053(2) 0.038(2) 0.047(2) -0.0035(17) -0.0305(17) 0.0135(16) C325 0.047(2) 0.036(2) 0.053(2) -0.0132(17) -0.0339(17) 0.0054(15) C326 0.0287(16) 0.0243(17) 0.0314(17) -0.0061(13) -0.0113(13) -0.0025(13) C331 0.0232(14) 0.0126(14) 0.0199(14) -0.0026(11) -0.0042(11) -0.0019(11) C332 0.0253(15) 0.0205(15) 0.0265(16) -0.0045(12) -0.0023(11) -0.0027(12) C333 0.0323(16) 0.0258(16) 0.0269(16) -0.0031(13) 0.0022(12) 0.0060(13) C334 0.051(2) 0.0263(17) 0.0250(16) -0.0113(13) -0.0015(14) 0.0021(14) C335 0.0443(19) 0.044(2) 0.0327(18) -0.0197(15) -0.0080(14) -0.0111(16) C336 0.0238(15) 0.0414(19) 0.0298(16) -0.0133(14) -0.0025(12) -0.0067(13) C411 0.0278(15) 0.0147(14) 0.0174(14) -0.0005(11) -0.0001(11) -0.0027(11) C412 0.0314(16) 0.0276(16) 0.0275(16) -0.0059(13) 0.0051(12) -0.0026(13) C413 0.045(2) 0.0324(18) 0.0317(18) -0.0069(14) 0.0131(14) 0.0012(15) C414 0.063(2) 0.0254(17) 0.0214(16) -0.0088(13) 0.0060(15) 0.0017(15) C415 0.056(2) 0.0246(17) 0.0230(16) -0.0071(13) -0.0112(14) 0.0001(14) C416 0.0317(16) 0.0243(16) 0.0222(15) -0.0013(12) -0.0054(12) -0.0003(12) C421 0.0174(13) 0.0193(15) 0.0186(14) -0.0003(11) 0.0013(10) -0.0040(11) C422 0.0217(14) 0.0189(15) 0.0390(18) -0.0035(13) -0.0048(12) -0.0029(12) C423 0.0258(16) 0.0259(17) 0.0430(19) -0.0017(14) -0.0110(13) 0.0038(13) C424 0.0202(14) 0.0337(17) 0.0325(17) -0.0040(13) -0.0081(12) -0.0026(13) C425 0.0274(15) 0.0308(17) 0.0279(16) -0.0120(13) -0.0050(12) -0.0080(13) C426 0.0259(15) 0.0226(16) 0.0252(15) -0.0050(12) -0.0015(12) -0.0018(12) C431 0.0256(14) 0.0144(14) 0.0180(14) -0.0012(11) -0.0029(11) -0.0017(11) C432 0.0325(16) 0.0241(16) 0.0282(16) 0.0046(13) -0.0007(12) -0.0072(13) C433 0.048(2) 0.0333(19) 0.0351(18) 0.0070(14) 0.0020(15) -0.0199(16) C434 0.068(2) 0.0200(17) 0.0295(17) 0.0056(13) -0.0035(16) -0.0116(16) C435 0.0462(19) 0.0201(17) 0.0315(17) -0.0015(13) -0.0057(14) 0.0089(14) C436 0.0307(16) 0.0241(17) 0.0241(15) -0.0013(13) -0.0009(12) -0.0050(13) C1S 0.045(2) 0.0282(18) 0.071(3) 0.0099(18) -0.0224(19) -0.0002(15) C2S 0.074(3) 0.044(2) 0.041(2) -0.0064(17) -0.0098(19) 0.0021(19) C3S 0.080(3) 0.067(3) 0.077(3) -0.017(2) -0.032(3) -0.001(2) C4S 0.066(3) 0.091(4) 0.112(4) -0.040(3) -0.019(3) -0.019(3) C5S 0.054(3) 0.126(4) 0.084(4) -0.045(3) 0.000(2) -0.019(3) C6S 0.053(3) 0.066(3) 0.071(3) -0.021(2) -0.025(2) 0.004(2) C7S 0.069(3) 0.068(3) 0.135(5) -0.012(3) -0.022(3) -0.007(2) C8S 0.070(3) 0.093(3) 0.105(3) 0.035(3) 0.005(3) 0.011(3) C9S 0.108(4) 0.043(2) 0.036(2) -0.0067(18) -0.021(2) 0.022(2) C10S 0.100(4) 0.103(4) 0.100(5) -0.011(3) -0.035(4) 0.008(3) C11S 0.084(4) 0.124(5) 0.079(4) -0.039(3) -0.019(3) -0.009(3) C12S 0.109(4) 0.113(4) 0.107(4) -0.037(3) -0.036(3) -0.006(3) C13S 0.079(3) 0.062(3) 0.076(3) -0.001(2) -0.041(3) -0.007(2) C14S 0.089(3) 0.129(4) 0.126(4) 0.056(3) 0.017(3) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru1 C13 2.157(3) . ? Ru1 C12 2.202(2) . ? Ru1 C11 2.244(2) . ? Ru1 N1 2.280(2) . ? Ru1 P1 2.2834(7) . ? Ru1 P2 2.3542(7) . ? Ru1 B1 2.357(3) . ? Ru1 Cl1 2.4514(6) . ? P1 C121 1.838(2) . ? P1 C131 1.845(3) . ? P1 C111 1.853(2) . ? P2 C221 1.833(3) . ? P2 C231 1.845(2) . ? P2 C211 1.852(3) . ? B1 N1 1.489(4) . ? B1 C11 1.515(4) . ? B1 C18 1.531(4) . ? N1 C13 1.426(3) . ? N1 C14 1.506(3) . ? C11 C12 1.426(4) . ? C12 C13 1.392(4) . ? C14 C17 1.518(3) . ? C14 C16 1.529(4) . ? C14 C15 1.531(4) . ? C18 C19 1.201(3) . ? C19 C101 1.439(4) . ? C101 C106 1.382(4) . ? C101 C102 1.390(4) . ? C102 C103 1.392(4) . ? C103 C104 1.369(4) . ? C104 C105 1.368(5) . ? C105 C106 1.390(4) . ? C111 C116 1.384(4) . ? C111 C112 1.400(3) . ? C112 C113 1.389(4) . ? C113 C114 1.372(4) . ? C114 C115 1.377(4) . ? C115 C116 1.394(3) . ? C121 C122 1.391(3) . ? C121 C126 1.397(3) . ? C122 C123 1.388(3) . ? C123 C124 1.369(4) . ? C124 C125 1.387(4) . ? C125 C126 1.380(3) . ? C131 C132 1.388(4) . ? C131 C136 1.394(3) . ? C132 C133 1.386(4) . ? C133 C134 1.376(4) . ? C134 C135 1.377(4) . ? C135 C136 1.385(4) . ? C211 C212 1.385(4) . ? C211 C216 1.393(3) . ? C212 C213 1.388(4) . ? C213 C214 1.380(4) . ? C214 C215 1.369(4) . ? C215 C216 1.390(4) . ? C221 C222 1.388(3) . ? C221 C226 1.400(3) . ? C222 C223 1.396(4) . ? C223 C224 1.365(4) . ? C224 C225 1.378(4) . ? C225 C226 1.375(4) . ? C231 C232 1.391(3) . ? C231 C236 1.395(4) . ? C232 C233 1.383(4) . ? C233 C234 1.374(4) . ? C234 C235 1.395(4) . ? C235 C236 1.384(4) . ? Ru2 C23 2.152(3) . ? Ru2 C22 2.205(2) . ? Ru2 C21 2.247(2) . ? Ru2 P4 2.2868(7) . ? Ru2 N2 2.288(2) . ? Ru2 P3 2.3499(7) . ? Ru2 B2 2.355(3) . ? Ru2 Cl2 2.4509(6) . ? P3 C321 1.842(3) . ? P3 C311 1.842(2) . ? P3 C331 1.849(3) . ? P4 C421 1.842(2) . ? P4 C411 1.845(3) . ? P4 C431 1.854(2) . ? B2 N2 1.493(4) . ? B2 C21 1.514(4) . ? B2 C28 1.534(4) . ? N2 C23 1.426(3) . ? N2 C24 1.503(3) . ? C21 C22 1.430(4) . ? C22 C23 1.389(3) . ? C24 C27 1.519(4) . ? C24 C26 1.521(3) . ? C24 C25 1.539(4) . ? C28 C29 1.194(3) . ? C29 C201 1.442(4) . ? C201 C202 1.400(4) . ? C201 C206 1.401(4) . ? C202 C203 1.383(4) . ? C203 C204 1.376(5) . ? C204 C205 1.370(4) . ? C205 C206 1.392(4) . ? C311 C316 1.389(3) . ? C311 C312 1.399(3) . ? C312 C313 1.387(4) . ? C313 C314 1.384(4) . ? C314 C315 1.373(4) . ? C315 C316 1.392(4) . ? C321 C326 1.385(3) . ? C321 C322 1.397(3) . ? C322 C323 1.380(4) . ? C323 C324 1.376(4) . ? C324 C325 1.368(4) . ? C325 C326 1.388(4) . ? C331 C332 1.391(4) . ? C331 C336 1.392(3) . ? C332 C333 1.384(4) . ? C333 C334 1.383(4) . ? C334 C335 1.376(4) . ? C335 C336 1.384(4) . ? C411 C412 1.392(4) . ? C411 C416 1.400(3) . ? C412 C413 1.391(4) . ? C413 C414 1.387(4) . ? C414 C415 1.369(4) . ? C415 C416 1.383(4) . ? C421 C426 1.386(3) . ? C421 C422 1.392(4) . ? C422 C423 1.388(3) . ? C423 C424 1.379(4) . ? C424 C425 1.372(4) . ? C425 C426 1.382(3) . ? C431 C436 1.381(4) . ? C431 C432 1.399(3) . ? C432 C433 1.387(4) . ? C433 C434 1.372(5) . ? C434 C435 1.375(4) . ? C435 C436 1.400(4) . ? C1S C2S 1.380(5) . ? C1S C6S 1.406(5) . ? C1S C7S 1.457(5) . ? C2S C3S 1.333(5) . ? C3S C4S 1.385(6) . ? C4S C5S 1.356(6) . ? C5S C6S 1.373(5) . ? C8S C13S 1.350(6) . ? C8S C14S 1.378(6) . ? C8S C9S 1.414(7) . ? C9S C10S 1.339(6) . ? C10S C11S 1.397(6) . ? C11S C12S 1.326(6) . ? C12S C13S 1.434(7) . ? 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 Ru1 C12 37.23(9) . . ? C13 Ru1 C11 63.21(10) . . ? C12 Ru1 C11 37.40(9) . . ? C13 Ru1 N1 37.37(8) . . ? C12 Ru1 N1 62.22(8) . . ? C11 Ru1 N1 63.57(8) . . ? C13 Ru1 P1 111.92(7) . . ? C12 Ru1 P1 85.40(7) . . ? C11 Ru1 P1 94.68(7) . . ? N1 Ru1 P1 147.14(5) . . ? C13 Ru1 P2 146.78(7) . . ? C12 Ru1 P2 147.41(7) . . ? C11 Ru1 P2 110.02(7) . . ? N1 Ru1 P2 109.49(5) . . ? P1 Ru1 P2 100.84(2) . . ? C13 Ru1 B1 62.53(10) . . ? C12 Ru1 B1 62.30(9) . . ? C11 Ru1 B1 38.34(9) . . ? N1 Ru1 B1 37.43(9) . . ? P1 Ru1 B1 132.13(7) . . ? P2 Ru1 B1 91.62(7) . . ? C13 Ru1 Cl1 92.68(7) . . ? C12 Ru1 Cl1 120.57(7) . . ? C11 Ru1 Cl1 155.77(7) . . ? N1 Ru1 Cl1 99.23(6) . . ? P1 Ru1 Cl1 92.25(2) . . ? P2 Ru1 Cl1 91.35(2) . . ? B1 Ru1 Cl1 133.82(8) . . ? C121 P1 C131 103.52(12) . . ? C121 P1 C111 102.10(11) . . ? C131 P1 C111 97.05(11) . . ? C121 P1 Ru1 112.02(8) . . ? C131 P1 Ru1 125.72(8) . . ? C111 P1 Ru1 113.20(9) . . ? C221 P2 C231 102.46(11) . . ? C221 P2 C211 97.18(12) . . ? C231 P2 C211 101.92(11) . . ? C221 P2 Ru1 119.69(8) . . ? C231 P2 Ru1 109.22(8) . . ? C211 P2 Ru1 123.27(8) . . ? N1 B1 C11 105.0(2) . . ? N1 B1 C18 126.8(2) . . ? C11 B1 C18 128.0(3) . . ? N1 B1 Ru1 68.48(14) . . ? C11 B1 Ru1 66.82(14) . . ? C18 B1 Ru1 132.25(19) . . ? C13 N1 B1 107.3(2) . . ? C13 N1 C14 117.6(2) . . ? B1 N1 C14 131.4(2) . . ? C13 N1 Ru1 66.65(13) . . ? B1 N1 Ru1 74.08(15) . . ? C14 N1 Ru1 139.93(16) . . ? C12 C11 B1 106.8(2) . . ? C12 C11 Ru1 69.67(13) . . ? B1 C11 Ru1 74.84(14) . . ? C13 C12 C11 110.0(2) . . ? C13 C12 Ru1 69.65(14) . . ? C11 C12 Ru1 72.93(13) . . ? C12 C13 N1 110.6(2) . . ? C12 C13 Ru1 73.12(15) . . ? N1 C13 Ru1 75.98(14) . . ? N1 C14 C17 110.0(2) . . ? N1 C14 C16 110.8(2) . . ? C17 C14 C16 109.4(2) . . ? N1 C14 C15 106.5(2) . . ? C17 C14 C15 109.7(2) . . ? C16 C14 C15 110.5(2) . . ? C19 C18 B1 174.6(3) . . ? C18 C19 C101 175.9(3) . . ? C106 C101 C102 118.6(3) . . ? C106 C101 C19 119.5(3) . . ? C102 C101 C19 121.9(2) . . ? C101 C102 C103 120.0(3) . . ? C104 C103 C102 120.4(3) . . ? C105 C104 C103 120.2(3) . . ? C104 C105 C106 119.8(3) . . ? C101 C106 C105 120.9(3) . . ? C116 C111 C112 118.6(2) . . ? C116 C111 P1 120.97(19) . . ? C112 C111 P1 120.3(2) . . ? C113 C112 C111 120.5(3) . . ? C114 C113 C112 119.8(3) . . ? C113 C114 C115 120.6(3) . . ? C114 C115 C116 119.9(3) . . ? C111 C116 C115 120.5(3) . . ? C122 C121 C126 117.7(2) . . ? C122 C121 P1 122.0(2) . . ? C126 C121 P1 120.06(17) . . ? C123 C122 C121 120.9(3) . . ? C124 C123 C122 120.5(2) . . ? C123 C124 C125 119.6(2) . . ? C126 C125 C124 120.0(3) . . ? C125 C126 C121 121.2(2) . . ? C132 C131 C136 118.7(3) . . ? C132 C131 P1 122.6(2) . . ? C136 C131 P1 118.1(2) . . ? C133 C132 C131 120.9(3) . . ? C134 C133 C132 119.9(3) . . ? C133 C134 C135 119.9(3) . . ? C134 C135 C136 120.7(3) . . ? C135 C136 C131 119.9(3) . . ? C212 C211 C216 118.0(2) . . ? C212 C211 P2 117.33(18) . . ? C216 C211 P2 124.6(2) . . ? C211 C212 C213 121.5(2) . . ? C214 C213 C212 119.7(3) . . ? C215 C214 C213 119.6(3) . . ? C214 C215 C216 120.9(3) . . ? C215 C216 C211 120.3(3) . . ? C222 C221 C226 118.3(2) . . ? C222 C221 P2 121.35(19) . . ? C226 C221 P2 120.38(18) . . ? C221 C222 C223 120.1(3) . . ? C224 C223 C222 120.5(3) . . ? C223 C224 C225 120.1(3) . . ? C226 C225 C224 120.0(3) . . ? C225 C226 C221 121.0(2) . . ? C232 C231 C236 118.3(2) . . ? C232 C231 P2 123.5(2) . . ? C236 C231 P2 118.1(2) . . ? C233 C232 C231 120.8(3) . . ? C234 C233 C232 120.7(3) . . ? C233 C234 C235 119.3(3) . . ? C236 C235 C234 120.1(3) . . ? C235 C236 C231 120.7(3) . . ? C23 Ru2 C22 37.15(9) . . ? C23 Ru2 C21 63.20(10) . . ? C22 Ru2 C21 37.46(9) . . ? C23 Ru2 P4 112.56(6) . . ? C22 Ru2 P4 86.01(7) . . ? C21 Ru2 P4 94.98(6) . . ? C23 Ru2 N2 37.30(8) . . ? C22 Ru2 N2 62.11(8) . . ? C21 Ru2 N2 63.51(8) . . ? P4 Ru2 N2 147.67(5) . . ? C23 Ru2 P3 146.82(7) . . ? C22 Ru2 P3 147.28(7) . . ? C21 Ru2 P3 109.83(7) . . ? P4 Ru2 P3 100.12(2) . . ? N2 Ru2 P3 109.59(5) . . ? C23 Ru2 B2 62.59(10) . . ? C22 Ru2 B2 62.36(9) . . ? C21 Ru2 B2 38.33(9) . . ? P4 Ru2 B2 132.32(7) . . ? N2 Ru2 B2 37.49(9) . . ? P3 Ru2 B2 91.47(7) . . ? C23 Ru2 Cl2 92.12(7) . . ? C22 Ru2 Cl2 119.99(7) . . ? C21 Ru2 Cl2 155.21(7) . . ? P4 Ru2 Cl2 92.41(2) . . ? N2 Ru2 Cl2 98.82(5) . . ? P3 Ru2 Cl2 92.03(2) . . ? B2 Ru2 Cl2 133.53(7) . . ? C321 P3 C311 102.82(11) . . ? C321 P3 C331 97.65(12) . . ? C311 P3 C331 100.87(11) . . ? C321 P3 Ru2 119.21(8) . . ? C311 P3 Ru2 109.52(8) . . ? C331 P3 Ru2 123.60(8) . . ? C421 P4 C411 103.49(12) . . ? C421 P4 C431 101.89(11) . . ? C411 P4 C431 97.09(11) . . ? C421 P4 Ru2 112.38(8) . . ? C411 P4 Ru2 125.52(8) . . ? C431 P4 Ru2 113.19(9) . . ? N2 B2 C21 105.0(2) . . ? N2 B2 C28 126.1(2) . . ? C21 B2 C28 128.6(2) . . ? N2 B2 Ru2 68.81(13) . . ? C21 B2 Ru2 66.98(14) . . ? C28 B2 Ru2 132.02(19) . . ? C23 N2 B2 107.1(2) . . ? C23 N2 C24 118.2(2) . . ? B2 N2 C24 131.2(2) . . ? C23 N2 Ru2 66.18(13) . . ? B2 N2 Ru2 73.71(14) . . ? C24 N2 Ru2 140.38(15) . . ? C22 C21 B2 106.8(2) . . ? C22 C21 Ru2 69.65(13) . . ? B2 C21 Ru2 74.69(14) . . ? C23 C22 C21 109.8(2) . . ? C23 C22 Ru2 69.37(14) . . ? C21 C22 Ru2 72.90(14) . . ? C22 C23 N2 110.9(2) . . ? C22 C23 Ru2 73.48(16) . . ? N2 C23 Ru2 76.52(14) . . ? N2 C24 C27 111.2(2) . . ? N2 C24 C26 110.5(2) . . ? C27 C24 C26 109.0(2) . . ? N2 C24 C25 106.0(2) . . ? C27 C24 C25 110.6(2) . . ? C26 C24 C25 109.5(2) . . ? C29 C28 B2 175.6(3) . . ? C28 C29 C201 174.9(3) . . ? C202 C201 C206 118.8(2) . . ? C202 C201 C29 119.6(2) . . ? C206 C201 C29 121.6(2) . . ? C203 C202 C201 120.7(3) . . ? C204 C203 C202 119.8(3) . . ? C205 C204 C203 120.7(3) . . ? C204 C205 C206 120.6(3) . . ? C205 C206 C201 119.5(3) . . ? C316 C311 C312 118.6(2) . . ? C316 C311 P3 123.74(19) . . ? C312 C311 P3 117.62(19) . . ? C313 C312 C311 120.7(3) . . ? C314 C313 C312 119.9(3) . . ? C315 C314 C313 119.7(3) . . ? C314 C315 C316 120.9(3) . . ? C311 C316 C315 120.0(3) . . ? C326 C321 C322 118.7(2) . . ? C326 C321 P3 120.87(19) . . ? C322 C321 P3 120.47(18) . . ? C323 C322 C321 120.7(3) . . ? C324 C323 C322 119.7(3) . . ? C325 C324 C323 120.4(3) . . ? C324 C325 C326 120.4(3) . . ? C321 C326 C325 120.1(3) . . ? C332 C331 C336 117.6(2) . . ? C332 C331 P3 117.59(18) . . ? C336 C331 P3 124.8(2) . . ? C333 C332 C331 121.3(2) . . ? C334 C333 C332 120.3(3) . . ? C335 C334 C333 119.1(3) . . ? C334 C335 C336 120.7(3) . . ? C335 C336 C331 121.0(3) . . ? C412 C411 C416 118.6(3) . . ? C412 C411 P4 122.3(2) . . ? C416 C411 P4 118.6(2) . . ? C413 C412 C411 120.6(3) . . ? C414 C413 C412 119.7(3) . . ? C415 C414 C413 120.1(3) . . ? C414 C415 C416 120.7(3) . . ? C415 C416 C411 120.2(3) . . ? C426 C421 C422 117.8(2) . . ? C426 C421 P4 122.4(2) . . ? C422 C421 P4 119.67(18) . . ? C423 C422 C421 120.7(2) . . ? C424 C423 C422 120.5(3) . . ? C425 C424 C423 119.1(2) . . ? C424 C425 C426 120.7(2) . . ? C425 C426 C421 121.2(3) . . ? C436 C431 C432 118.8(2) . . ? C436 C431 P4 120.44(19) . . ? C432 C431 P4 120.6(2) . . ? C433 C432 C431 120.1(3) . . ? C434 C433 C432 120.7(3) . . ? C433 C434 C435 119.8(3) . . ? C434 C435 C436 120.2(3) . . ? C431 C436 C435 120.4(3) . . ? C2S C1S C6S 118.0(3) . . ? C2S C1S C7S 122.6(4) . . ? C6S C1S C7S 119.3(4) . . ? C3S C2S C1S 122.3(4) . . ? C2S C3S C4S 120.0(4) . . ? C5S C4S C3S 119.1(4) . . ? C4S C5S C6S 121.9(4) . . ? C5S C6S C1S 118.7(4) . . ? C13S C8S C14S 124.8(7) . . ? C13S C8S C9S 119.9(5) . . ? C14S C8S C9S 115.1(6) . . ? C10S C9S C8S 118.0(5) . . ? C9S C10S C11S 123.9(6) . . ? C12S C11S C10S 117.4(6) . . ? C11S C12S C13S 121.4(5) . . ? C8S C13S C12S 119.2(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.085 _refine_diff_density_min -0.675 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 908726' ####################################################################### # # 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_compound-2 # start Validation Reply Form _vrf_PLAT220_compound-2 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.4 Ratio RESPONSE: The non-solvent carbon atoms with large Ueq values are due to the terminal methyl carbons of the tert-butyl group (C5, C6 and C7). The large Ueq values are attributed to the partially non-resolved disorder effects derived from the thermal motion of the terminal methyl carbons, which may adopt physically less meaningful values. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C51 H48 B N P2 Ru' _chemical_formula_sum 'C51 H48 B N P2 Ru' _chemical_formula_weight 848.72 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' B B 0.0013 0.0007 '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' 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 9.9813(4) _cell_length_b 14.1738(5) _cell_length_c 29.0404(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4108.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6957 _cell_measurement_theta_min 2.8014 _cell_measurement_theta_max 29.0928 _exptl_crystal_description block _exptl_crystal_colour orange-red _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.497 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95632 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12358 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7826 _reflns_number_gt 6617 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0013P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.042(16) _refine_ls_number_reflns 7826 _refine_ls_number_parameters 508 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0412 _refine_ls_wR_factor_gt 0.0403 _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_restrained_S_all 0.915 _refine_ls_shift/su_max 0.004 _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 0.88609(2) 0.521371(15) 0.924859(8) 0.01018(5) Uani 1 1 d . . . H1 H 1.0290(17) 0.4986(15) 0.9236(7) 0.015 Uiso 1 1 d . . . P1 P 0.95133(7) 0.60173(5) 0.86024(3) 0.01153(18) Uani 1 1 d . . . P2 P 0.87882(7) 0.37177(5) 0.89525(2) 0.01148(15) Uani 1 1 d . . . B1 B 0.7694(3) 0.6516(2) 0.95942(12) 0.0153(8) Uani 1 1 d . . . N1 N 0.6856(2) 0.56541(16) 0.96397(8) 0.0122(6) Uani 1 1 d . . . C1 C 0.8999(3) 0.62624(19) 0.98312(9) 0.0163(7) Uani 1 1 d . . . H1A H 0.9764 0.6702 0.9890 0.020 Uiso 1 1 calc R . . C2 C 0.8869(3) 0.5341(2) 1.00096(8) 0.0182(6) Uani 1 1 d . . . H2A H 0.9517 0.5025 1.0222 0.022 Uiso 1 1 calc R . . C3 C 0.7639(2) 0.49647(19) 0.98645(9) 0.0144(7) Uani 1 1 d . . . H3A H 0.7295 0.4331 0.9959 0.017 Uiso 1 1 calc R . . C4 C 0.5357(3) 0.5484(2) 0.96084(11) 0.0177(7) Uani 1 1 d . . . C5 C 0.4679(3) 0.6293(2) 0.93679(13) 0.0496(12) Uani 1 1 d . . . H5A H 0.5026 0.6347 0.9053 0.074 Uiso 1 1 calc R . . H5B H 0.4857 0.6879 0.9536 0.074 Uiso 1 1 calc R . . H5C H 0.3711 0.6179 0.9358 0.074 Uiso 1 1 calc R . . C6 C 0.4810(3) 0.5439(3) 1.00965(10) 0.0456(12) Uani 1 1 d . . . H6A H 0.3840 0.5337 1.0086 0.068 Uiso 1 1 calc R . . H6B H 0.5002 0.6034 1.0256 0.068 Uiso 1 1 calc R . . H6C H 0.5237 0.4917 1.0262 0.068 Uiso 1 1 calc R . . C7 C 0.5064(2) 0.4582(2) 0.93573(12) 0.0448(11) Uani 1 1 d . . . H7A H 0.5415 0.4622 0.9043 0.067 Uiso 1 1 calc R . . H7B H 0.4093 0.4480 0.9347 0.067 Uiso 1 1 calc R . . H7C H 0.5491 0.4054 0.9518 0.067 Uiso 1 1 calc R . . C8 C 0.7280(3) 0.7448(2) 0.93715(10) 0.0189(8) Uani 1 1 d . . . C9 C 0.7024(3) 0.8167(2) 0.91701(11) 0.0191(8) Uani 1 1 d . . . C10 C 0.6685(3) 0.8976(2) 0.88953(10) 0.0185(7) Uani 1 1 d . . . C11 C 0.5383(3) 0.9075(2) 0.87215(10) 0.0259(8) Uani 1 1 d . . . H11A H 0.4712 0.8630 0.8802 0.031 Uiso 1 1 calc R . . C12 C 0.5076(3) 0.9811(3) 0.84363(10) 0.0310(8) Uani 1 1 d . . . H12A H 0.4186 0.9879 0.8325 0.037 Uiso 1 1 calc R . . C13 C 0.6037(3) 1.0451(2) 0.83079(10) 0.0325(8) Uani 1 1 d . . . H13A H 0.5821 1.0951 0.8103 0.039 Uiso 1 1 calc R . . C14 C 0.7322(3) 1.0362(2) 0.84800(11) 0.0317(8) Uani 1 1 d . . . H14A H 0.7990 1.0809 0.8397 0.038 Uiso 1 1 calc R . . C15 C 0.7632(3) 0.9635(2) 0.87683(10) 0.0226(8) Uani 1 1 d . . . H15A H 0.8519 0.9580 0.8884 0.027 Uiso 1 1 calc R . . C16 C 0.8274(3) 0.6382(2) 0.81724(10) 0.0142(7) Uani 1 1 d . . . C17 C 0.6952(3) 0.6532(2) 0.83130(11) 0.0185(8) Uani 1 1 d . . . H17A H 0.6709 0.6408 0.8623 0.022 Uiso 1 1 calc R . . C18 C 0.5992(3) 0.6857(2) 0.80086(11) 0.0277(8) Uani 1 1 d . . . H18A H 0.5097 0.6949 0.8110 0.033 Uiso 1 1 calc R . . C19 C 0.6334(3) 0.7047(2) 0.75589(11) 0.0314(9) Uani 1 1 d . . . H19A H 0.5680 0.7286 0.7351 0.038 Uiso 1 1 calc R . . C20 C 0.7615(3) 0.6893(2) 0.74114(11) 0.0308(9) Uani 1 1 d . . . H20A H 0.7842 0.7002 0.7098 0.037 Uiso 1 1 calc R . . C21 C 0.8576(3) 0.6580(2) 0.77147(10) 0.0204(7) Uani 1 1 d . . . H21A H 0.9469 0.6498 0.7609 0.024 Uiso 1 1 calc R . . C22 C 1.0366(2) 0.71430(19) 0.87268(9) 0.0112(7) Uani 1 1 d . . . C23 C 1.0228(3) 0.7945(2) 0.84598(10) 0.0180(7) Uani 1 1 d . . . H23A H 0.9610 0.7942 0.8211 0.022 Uiso 1 1 calc R . . C24 C 1.0962(3) 0.8748(2) 0.85457(11) 0.0229(7) Uani 1 1 d . . . H24A H 1.0857 0.9287 0.8355 0.027 Uiso 1 1 calc R . . C25 C 1.1859(3) 0.8770(2) 0.89132(11) 0.0221(8) Uani 1 1 d . . . H25A H 1.2364 0.9324 0.8975 0.027 Uiso 1 1 calc R . . C26 C 1.2009(2) 0.7980(2) 0.91865(12) 0.0204(7) Uani 1 1 d . . . H26A H 1.2625 0.7986 0.9436 0.025 Uiso 1 1 calc R . . C27 C 1.1258(3) 0.71776(18) 0.90959(9) 0.0175(7) Uani 1 1 d . . . H27A H 1.1354 0.6641 0.9289 0.021 Uiso 1 1 calc R . . C28 C 1.0799(2) 0.54833(19) 0.82243(9) 0.0128(7) Uani 1 1 d . . . C29 C 1.2160(2) 0.5653(2) 0.82878(10) 0.0152(7) Uani 1 1 d . . . H29A H 1.2443 0.6104 0.8509 0.018 Uiso 1 1 calc R . . C30 C 1.3110(2) 0.5165(2) 0.80299(9) 0.0211(7) Uani 1 1 d . . . H30A H 1.4036 0.5284 0.8078 0.025 Uiso 1 1 calc R . . C31 C 1.2723(3) 0.4517(2) 0.77084(10) 0.0243(8) Uani 1 1 d . . . H31A H 1.3378 0.4188 0.7534 0.029 Uiso 1 1 calc R . . C32 C 1.1372(3) 0.4338(2) 0.76367(10) 0.0227(7) Uani 1 1 d . . . H32A H 1.1099 0.3887 0.7414 0.027 Uiso 1 1 calc R . . C33 C 1.0427(3) 0.4821(2) 0.78919(8) 0.0176(6) Uani 1 1 d . . . H33A H 0.9503 0.4701 0.7840 0.021 Uiso 1 1 calc R . . C34 C 1.0370(3) 0.3021(2) 0.89144(10) 0.0120(7) Uani 1 1 d . . . C35 C 1.1564(2) 0.3457(2) 0.87956(9) 0.0151(7) Uani 1 1 d . . . H35A H 1.1583 0.4120 0.8749 0.018 Uiso 1 1 calc R . . C36 C 1.2737(3) 0.2935(2) 0.87441(10) 0.0196(7) Uani 1 1 d . . . H36A H 1.3546 0.3246 0.8663 0.024 Uiso 1 1 calc R . . C37 C 1.2736(3) 0.1977(2) 0.88093(10) 0.0232(8) Uani 1 1 d . . . H37A H 1.3537 0.1624 0.8770 0.028 Uiso 1 1 calc R . . C38 C 1.1565(3) 0.1534(2) 0.89318(11) 0.0275(9) Uani 1 1 d . . . H38A H 1.1563 0.0873 0.8985 0.033 Uiso 1 1 calc R . . C39 C 1.0391(3) 0.2043(2) 0.89781(10) 0.0204(7) Uani 1 1 d . . . H39A H 0.9585 0.1722 0.9055 0.024 Uiso 1 1 calc R . . C40 C 0.7825(2) 0.28714(19) 0.93024(10) 0.0139(7) Uani 1 1 d . . . C41 C 0.8265(2) 0.2730(2) 0.97511(10) 0.0176(7) Uani 1 1 d . . . H41A H 0.8980 0.3101 0.9868 0.021 Uiso 1 1 calc R . . C42 C 0.7680(3) 0.2057(2) 1.00279(10) 0.0187(7) Uani 1 1 d . . . H42A H 0.8002 0.1964 1.0332 0.022 Uiso 1 1 calc R . . C43 C 0.6630(3) 0.1518(2) 0.98670(10) 0.0201(8) Uani 1 1 d . . . H43A H 0.6223 0.1053 1.0057 0.024 Uiso 1 1 calc R . . C44 C 0.6184(3) 0.16684(19) 0.94238(9) 0.0223(7) Uani 1 1 d . . . H44A H 0.5465 0.1300 0.9307 0.027 Uiso 1 1 calc R . . C45 C 0.6763(2) 0.23431(19) 0.91466(10) 0.0165(7) Uani 1 1 d . . . H45A H 0.6424 0.2445 0.8845 0.020 Uiso 1 1 calc R . . C46 C 0.8078(3) 0.3493(2) 0.83745(9) 0.0115(7) Uani 1 1 d . . . C47 C 0.7096(2) 0.4117(2) 0.82185(10) 0.0134(7) Uani 1 1 d . . . H47A H 0.6795 0.4610 0.8414 0.016 Uiso 1 1 calc R . . C48 C 0.6553(3) 0.4023(2) 0.77779(10) 0.0202(8) Uani 1 1 d . . . H48A H 0.5890 0.4455 0.7674 0.024 Uiso 1 1 calc R . . C49 C 0.6976(3) 0.3310(2) 0.74954(11) 0.0233(8) Uani 1 1 d . . . H49A H 0.6614 0.3252 0.7194 0.028 Uiso 1 1 calc R . . C50 C 0.7936(3) 0.2668(2) 0.76482(10) 0.0199(8) Uani 1 1 d . . . H50A H 0.8214 0.2162 0.7457 0.024 Uiso 1 1 calc R . . C51 C 0.8476(3) 0.2781(2) 0.80825(10) 0.0172(7) Uani 1 1 d . . . H51A H 0.9145 0.2351 0.8183 0.021 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 0.01090(10) 0.00985(9) 0.00979(10) 0.00045(13) 0.00005(12) 0.00107(10) P1 0.0122(4) 0.0106(4) 0.0117(4) 0.0012(4) -0.0020(4) -0.0007(3) P2 0.0125(4) 0.0118(4) 0.0102(4) 0.0004(3) -0.0010(4) 0.0006(3) B1 0.0179(19) 0.0154(19) 0.013(2) -0.0031(17) 0.0053(17) -0.0011(14) N1 0.0119(12) 0.0123(13) 0.0125(14) -0.0001(12) 0.0002(12) 0.0041(10) C1 0.0152(16) 0.0182(15) 0.0156(16) -0.0054(14) -0.0001(15) -0.0001(14) C2 0.0176(13) 0.0324(18) 0.0047(13) -0.0033(15) -0.0026(14) 0.0089(17) C3 0.0203(15) 0.0117(19) 0.0113(15) 0.0021(13) 0.0051(13) 0.0016(11) C4 0.0103(14) 0.0196(18) 0.0230(19) -0.0038(15) 0.0002(15) 0.0009(12) C5 0.0101(16) 0.057(3) 0.082(3) 0.026(3) -0.008(2) -0.0004(16) C6 0.0154(17) 0.092(4) 0.030(2) -0.004(2) 0.0098(16) -0.0042(19) C7 0.0139(16) 0.046(3) 0.074(3) -0.034(2) 0.0058(18) -0.0063(14) C8 0.0161(15) 0.0167(17) 0.024(2) -0.0050(16) 0.0066(15) -0.0023(13) C9 0.0154(15) 0.0177(17) 0.024(2) -0.0018(17) 0.0076(15) -0.0004(12) C10 0.0234(17) 0.0144(17) 0.0178(18) -0.0015(16) 0.0042(15) 0.0032(13) C11 0.0228(18) 0.0211(19) 0.034(2) 0.0017(18) 0.0016(16) 0.0016(14) C12 0.0346(19) 0.0260(18) 0.032(2) -0.001(2) -0.0057(16) 0.0117(18) C13 0.058(2) 0.0202(18) 0.0196(17) 0.0007(15) -0.002(2) 0.0123(19) C14 0.0392(19) 0.022(2) 0.033(2) 0.0038(19) 0.0110(17) -0.0018(16) C15 0.0229(16) 0.0166(19) 0.0283(19) 0.0003(17) 0.0019(15) 0.0012(14) C16 0.0207(17) 0.0067(16) 0.0153(17) 0.0002(15) -0.0035(14) -0.0022(12) C17 0.0166(17) 0.0182(18) 0.0208(19) -0.0022(16) -0.0041(15) 0.0022(13) C18 0.0190(18) 0.0242(18) 0.040(2) -0.0032(18) -0.0139(18) -0.0006(15) C19 0.032(2) 0.0233(18) 0.039(2) 0.0052(18) -0.027(2) 0.0010(17) C20 0.042(2) 0.037(2) 0.0139(19) 0.0101(18) -0.0148(18) -0.0032(17) C21 0.0150(18) 0.0272(18) 0.0190(17) 0.0065(16) -0.0036(15) -0.0031(13) C22 0.0091(14) 0.0125(16) 0.0121(16) -0.0045(14) 0.0016(13) 0.0035(12) C23 0.0179(16) 0.0152(17) 0.0210(18) 0.0024(16) -0.0039(15) -0.0008(13) C24 0.0214(18) 0.0152(16) 0.0321(19) 0.0056(16) 0.0013(17) 0.0020(14) C25 0.0124(16) 0.0143(17) 0.040(2) -0.0110(18) 0.0073(16) -0.0053(13) C26 0.0131(14) 0.0217(17) 0.026(2) -0.0096(18) -0.0020(16) -0.0024(12) C27 0.0189(15) 0.0161(15) 0.0174(17) 0.0009(13) 0.0021(16) 0.0045(14) C28 0.0156(17) 0.0125(16) 0.0102(15) 0.0019(13) 0.0035(12) 0.0005(11) C29 0.0167(16) 0.0119(16) 0.0171(18) -0.0021(15) -0.0012(14) -0.0028(13) C30 0.0136(14) 0.0216(16) 0.0280(18) 0.0011(19) 0.0056(13) -0.0008(14) C31 0.0301(18) 0.0203(19) 0.0226(18) -0.0047(16) 0.0127(16) -0.0030(14) C32 0.033(2) 0.0189(16) 0.0157(16) -0.0018(15) 0.0028(16) -0.0095(15) C33 0.0186(14) 0.0178(15) 0.0164(15) 0.0004(17) 0.0018(13) -0.0051(14) C34 0.0189(15) 0.0095(15) 0.0076(16) -0.0035(14) -0.0010(14) -0.0004(12) C35 0.0199(17) 0.0155(16) 0.0098(16) 0.0022(14) -0.0025(13) 0.0040(12) C36 0.0165(16) 0.030(2) 0.0125(17) -0.0059(17) -0.0032(14) 0.0046(14) C37 0.0215(17) 0.029(2) 0.0187(19) -0.0068(17) -0.0071(16) 0.0145(15) C38 0.041(2) 0.0146(17) 0.027(2) -0.0040(17) -0.0028(17) 0.0086(15) C39 0.0223(16) 0.0174(17) 0.0214(18) 0.0006(17) 0.0028(16) 0.0021(13) C40 0.0167(15) 0.0129(15) 0.0121(17) -0.0017(16) 0.0040(15) 0.0045(12) C41 0.0167(16) 0.0184(17) 0.0177(18) 0.0049(16) -0.0012(14) -0.0043(13) C42 0.0240(17) 0.0223(18) 0.0097(17) 0.0014(16) -0.0042(14) 0.0031(14) C43 0.0254(18) 0.0163(17) 0.0185(18) 0.0038(16) 0.0076(15) -0.0033(13) C44 0.0175(14) 0.0253(17) 0.0240(18) 0.0024(15) -0.0042(17) -0.0044(16) C45 0.0170(15) 0.0211(17) 0.0113(19) 0.0014(15) -0.0005(14) -0.0027(13) C46 0.0104(15) 0.0148(17) 0.0094(17) 0.0000(14) 0.0035(13) -0.0027(12) C47 0.0133(15) 0.0140(17) 0.0128(17) -0.0013(15) 0.0035(14) -0.0004(12) C48 0.0131(17) 0.031(2) 0.0162(17) 0.0044(17) -0.0051(14) -0.0011(13) C49 0.0184(18) 0.038(2) 0.0132(19) -0.0068(18) -0.0021(15) -0.0067(15) C50 0.0174(17) 0.027(2) 0.0154(18) -0.0065(17) 0.0043(15) -0.0013(14) C51 0.0158(17) 0.0163(17) 0.0193(18) -0.0001(15) -0.0030(14) 0.0001(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru1 C3 2.194(2) . ? Ru1 C2 2.217(2) . ? Ru1 C1 2.256(3) . ? Ru1 P2 2.2893(7) . ? Ru1 P1 2.2897(8) . ? Ru1 N1 2.384(2) . ? Ru1 B1 2.402(3) . ? Ru1 H1 1.463(18) . ? P1 C16 1.832(3) . ? P1 C22 1.844(3) . ? P1 C28 1.850(3) . ? P2 C40 1.843(3) . ? P2 C46 1.850(3) . ? P2 C34 1.865(3) . ? B1 N1 1.486(4) . ? B1 C1 1.517(4) . ? B1 C8 1.528(4) . ? N1 C3 1.411(3) . ? N1 C4 1.518(3) . ? C1 C2 1.412(4) . ? C1 H1A 1.0000 . ? C2 C3 1.403(3) . ? C2 H2A 1.0000 . ? C3 H3A 1.0000 . ? C4 C7 1.501(4) . ? C4 C5 1.503(4) . ? C4 C6 1.520(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.204(4) . ? C9 C10 1.437(4) . ? C10 C15 1.379(4) . ? C10 C11 1.401(4) . ? C11 C12 1.366(4) . ? C11 H11A 0.9500 . ? C12 C13 1.372(4) . ? C12 H12A 0.9500 . ? C13 C14 1.383(4) . ? C13 H13A 0.9500 . ? C14 C15 1.364(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C21 1.392(4) . ? C16 C17 1.397(4) . ? C17 C18 1.383(4) . ? C17 H17A 0.9500 . ? C18 C19 1.377(4) . ? C18 H18A 0.9500 . ? C19 C20 1.366(4) . ? C19 H19A 0.9500 . ? C20 C21 1.376(4) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.383(4) . ? C22 C27 1.395(3) . ? C23 C24 1.377(4) . ? C23 H23A 0.9500 . ? C24 C25 1.394(4) . ? C24 H24A 0.9500 . ? C25 C26 1.381(4) . ? C25 H25A 0.9500 . ? C26 C27 1.387(4) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C28 C29 1.392(3) . ? C28 C33 1.396(4) . ? C29 C30 1.392(4) . ? C29 H29A 0.9500 . ? C30 C31 1.366(4) . ? C30 H30A 0.9500 . ? C31 C32 1.388(3) . ? C31 H31A 0.9500 . ? C32 C33 1.381(4) . ? C32 H32A 0.9500 . ? C33 H33A 0.9500 . ? C34 C35 1.386(3) . ? C34 C39 1.400(4) . ? C35 C36 1.393(3) . ? C35 H35A 0.9500 . ? C36 C37 1.370(4) . ? C36 H36A 0.9500 . ? C37 C38 1.374(4) . ? C37 H37A 0.9500 . ? C38 C39 1.383(4) . ? C38 H38A 0.9500 . ? C39 H39A 0.9500 . ? C40 C45 1.375(4) . ? C40 C41 1.390(4) . ? C41 C42 1.377(4) . ? C41 H41A 0.9500 . ? C42 C43 1.379(4) . ? C42 H42A 0.9500 . ? C43 C44 1.379(4) . ? C43 H43A 0.9500 . ? C44 C45 1.377(4) . ? C44 H44A 0.9500 . ? C45 H45A 0.9500 . ? C46 C51 1.377(4) . ? C46 C47 1.396(4) . ? C47 C48 1.396(4) . ? C47 H47A 0.9500 . ? C48 C49 1.369(4) . ? C48 H48A 0.9500 . ? C49 C50 1.394(4) . ? C49 H49A 0.9500 . ? C50 C51 1.381(4) . ? C50 H50A 0.9500 . ? C51 H51A 0.9500 . ? 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 C3 Ru1 C2 37.09(9) . . ? C3 Ru1 C1 61.88(10) . . ? C2 Ru1 C1 36.77(10) . . ? C3 Ru1 P2 98.02(7) . . ? C2 Ru1 P2 116.72(8) . . ? C1 Ru1 P2 153.35(7) . . ? C3 Ru1 P1 155.02(7) . . ? C2 Ru1 P1 140.85(8) . . ? C1 Ru1 P1 105.63(7) . . ? P2 Ru1 P1 99.32(3) . . ? C3 Ru1 N1 35.60(8) . . ? C2 Ru1 N1 60.45(8) . . ? C1 Ru1 N1 61.42(9) . . ? P2 Ru1 N1 113.26(6) . . ? P1 Ru1 N1 119.93(6) . . ? C3 Ru1 B1 60.87(11) . . ? C2 Ru1 B1 61.50(11) . . ? C1 Ru1 B1 37.84(10) . . ? P2 Ru1 B1 148.56(8) . . ? P1 Ru1 B1 95.64(9) . . ? N1 Ru1 B1 36.17(9) . . ? C3 Ru1 H1 121.8(8) . . ? C2 Ru1 H1 92.3(8) . . ? C1 Ru1 H1 96.0(9) . . ? P2 Ru1 H1 79.5(8) . . ? P1 Ru1 H1 79.1(8) . . ? N1 Ru1 H1 152.7(9) . . ? B1 Ru1 H1 130.8(9) . . ? C16 P1 C22 101.58(13) . . ? C16 P1 C28 100.32(13) . . ? C22 P1 C28 98.64(12) . . ? C16 P1 Ru1 120.46(10) . . ? C22 P1 Ru1 113.65(9) . . ? C28 P1 Ru1 118.69(9) . . ? C40 P2 C46 100.86(13) . . ? C40 P2 C34 97.47(12) . . ? C46 P2 C34 100.32(12) . . ? C40 P2 Ru1 114.35(9) . . ? C46 P2 Ru1 120.84(10) . . ? C34 P2 Ru1 119.05(9) . . ? N1 B1 C1 104.4(3) . . ? N1 B1 C8 126.6(3) . . ? C1 B1 C8 129.0(3) . . ? N1 B1 Ru1 71.25(16) . . ? C1 B1 Ru1 65.87(15) . . ? C8 B1 Ru1 128.2(2) . . ? C3 N1 B1 107.4(2) . . ? C3 N1 C4 117.6(2) . . ? B1 N1 C4 132.8(2) . . ? C3 N1 Ru1 64.83(13) . . ? B1 N1 Ru1 72.58(15) . . ? C4 N1 Ru1 139.20(19) . . ? C2 C1 B1 107.8(3) . . ? C2 C1 Ru1 70.12(15) . . ? B1 C1 Ru1 76.30(16) . . ? C2 C1 H1A 125.8 . . ? B1 C1 H1A 125.8 . . ? Ru1 C1 H1A 125.8 . . ? C3 C2 C1 108.8(2) . . ? C3 C2 Ru1 70.54(14) . . ? C1 C2 Ru1 73.11(15) . . ? C3 C2 H2A 125.5 . . ? C1 C2 H2A 125.5 . . ? Ru1 C2 H2A 125.5 . . ? C2 C3 N1 111.1(2) . . ? C2 C3 Ru1 72.38(14) . . ? N1 C3 Ru1 79.57(15) . . ? C2 C3 H3A 124.0 . . ? N1 C3 H3A 124.0 . . ? Ru1 C3 H3A 124.0 . . ? C7 C4 C5 109.6(3) . . ? C7 C4 N1 110.9(2) . . ? C5 C4 N1 110.5(3) . . ? C7 C4 C6 110.3(3) . . ? C5 C4 C6 107.7(3) . . ? N1 C4 C6 107.7(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 B1 175.0(3) . . ? C8 C9 C10 175.0(3) . . ? C15 C10 C11 118.1(3) . . ? C15 C10 C9 121.8(3) . . ? C11 C10 C9 119.9(3) . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C12 C13 C14 119.3(3) . . ? C12 C13 H13A 120.3 . . ? C14 C13 H13A 120.3 . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 C15 C10 121.4(3) . . ? C14 C15 H15A 119.3 . . ? C10 C15 H15A 119.3 . . ? C21 C16 C17 117.0(3) . . ? C21 C16 P1 124.2(2) . . ? C17 C16 P1 118.8(2) . . ? C18 C17 C16 121.2(3) . . ? C18 C17 H17A 119.4 . . ? C16 C17 H17A 119.4 . . ? C19 C18 C17 120.0(3) . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19A 120.1 . . ? C18 C19 H19A 120.1 . . ? C19 C20 C21 120.2(3) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C20 C21 C16 121.7(3) . . ? C20 C21 H21A 119.2 . . ? C16 C21 H21A 119.2 . . ? C23 C22 C27 117.8(3) . . ? C23 C22 P1 123.7(2) . . ? C27 C22 P1 118.4(2) . . ? C24 C23 C22 121.7(3) . . ? C24 C23 H23A 119.2 . . ? C22 C23 H23A 119.2 . . ? C23 C24 C25 120.0(3) . . ? C23 C24 H24A 120.0 . . ? C25 C24 H24A 120.0 . . ? C26 C25 C24 119.5(3) . . ? C26 C25 H25A 120.3 . . ? C24 C25 H25A 120.3 . . ? C25 C26 C27 119.8(3) . . ? C25 C26 H26A 120.1 . . ? C27 C26 H26A 120.1 . . ? C26 C27 C22 121.3(3) . . ? C26 C27 H27A 119.3 . . ? C22 C27 H27A 119.3 . . ? C29 C28 C33 117.8(2) . . ? C29 C28 P1 121.8(2) . . ? C33 C28 P1 120.05(19) . . ? C30 C29 C28 120.5(3) . . ? C30 C29 H29A 119.7 . . ? C28 C29 H29A 119.7 . . ? C31 C30 C29 120.6(3) . . ? C31 C30 H30A 119.7 . . ? C29 C30 H30A 119.7 . . ? C30 C31 C32 120.0(3) . . ? C30 C31 H31A 120.0 . . ? C32 C31 H31A 120.0 . . ? C33 C32 C31 119.5(3) . . ? C33 C32 H32A 120.2 . . ? C31 C32 H32A 120.2 . . ? C32 C33 C28 121.5(2) . . ? C32 C33 H33A 119.2 . . ? C28 C33 H33A 119.2 . . ? C35 C34 C39 117.4(3) . . ? C35 C34 P2 120.5(2) . . ? C39 C34 P2 122.0(2) . . ? C34 C35 C36 120.9(3) . . ? C34 C35 H35A 119.6 . . ? C36 C35 H35A 119.6 . . ? C37 C36 C35 120.7(3) . . ? C37 C36 H36A 119.6 . . ? C35 C36 H36A 119.6 . . ? C36 C37 C38 119.3(3) . . ? C36 C37 H37A 120.3 . . ? C38 C37 H37A 120.3 . . ? C37 C38 C39 120.5(3) . . ? C37 C38 H38A 119.7 . . ? C39 C38 H38A 119.7 . . ? C38 C39 C34 121.1(3) . . ? C38 C39 H39A 119.4 . . ? C34 C39 H39A 119.4 . . ? C45 C40 C41 118.3(3) . . ? C45 C40 P2 125.1(2) . . ? C41 C40 P2 116.5(2) . . ? C42 C41 C40 120.9(3) . . ? C42 C41 H41A 119.6 . . ? C40 C41 H41A 119.6 . . ? C43 C42 C41 120.6(3) . . ? C43 C42 H42A 119.7 . . ? C41 C42 H42A 119.7 . . ? C44 C43 C42 118.4(3) . . ? C44 C43 H43A 120.8 . . ? C42 C43 H43A 120.8 . . ? C43 C44 C45 121.2(3) . . ? C43 C44 H44A 119.4 . . ? C45 C44 H44A 119.4 . . ? C40 C45 C44 120.6(3) . . ? C40 C45 H45A 119.7 . . ? C44 C45 H45A 119.7 . . ? C51 C46 C47 117.8(3) . . ? C51 C46 P2 125.1(2) . . ? C47 C46 P2 117.0(2) . . ? C48 C47 C46 120.7(3) . . ? C48 C47 H47A 119.7 . . ? C46 C47 H47A 119.7 . . ? C49 C48 C47 120.0(3) . . ? C49 C48 H48A 120.0 . . ? C47 C48 H48A 120.0 . . ? C48 C49 C50 120.2(3) . . ? C48 C49 H49A 119.9 . . ? C50 C49 H49A 119.9 . . ? C51 C50 C49 118.9(3) . . ? C51 C50 H50A 120.5 . . ? C49 C50 H50A 120.5 . . ? C46 C51 C50 122.3(3) . . ? C46 C51 H51A 118.8 . . ? C50 C51 H51A 118.8 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.614 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 908727' ####################################################################### # # 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_compound-5c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 O7' _chemical_formula_sum 'C15 H14 O7' _chemical_formula_weight 306.26 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 0.0000 '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' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.1386(7) _cell_length_b 6.5567(5) _cell_length_c 11.6157(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.023(6) _cell_angle_gamma 90.00 _cell_volume 694.29(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1836 _cell_measurement_theta_min 2.7449 _cell_measurement_theta_max 28.7645 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95148 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3444 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1489 _reflns_number_gt 1231 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. There is no significant anomalous scattering, so the Friedel pairs were merged and the absolute configuration was unknown. ; _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^)+(0.0317P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 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 ? _chemical_absolute_configuration unk _refine_ls_number_reflns 1489 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0647 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.008 _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 O1 O 0.2773(2) 0.6836(3) 0.26087(15) 0.0383(5) Uani 1 1 d . . . O2 O 0.31275(19) 0.4574(3) 0.40332(13) 0.0309(4) Uani 1 1 d . . . O3 O 0.3592(2) 0.1788(4) 0.51030(14) 0.0460(6) Uani 1 1 d . . . O4 O 1.0450(2) 0.1957(4) 0.28829(19) 0.0623(7) Uani 1 1 d . . . O5 O 0.88302(19) -0.0042(3) 0.36751(14) 0.0351(5) Uani 1 1 d . . . O6 O 0.7667(2) 0.7039(4) 0.07162(18) 0.0569(7) Uani 1 1 d . . . O7 O 0.97442(19) 0.5389(3) 0.12591(13) 0.0330(5) Uani 1 1 d . . . C1 C 0.5420(3) 0.1030(4) 0.28268(19) 0.0235(6) Uani 1 1 d . . . H1A H 0.5734 -0.0358 0.3102 0.028 Uiso 1 1 calc R . . C2 C 0.6405(3) 0.2791(4) 0.32773(18) 0.0194(5) Uani 1 1 d . . . H2A H 0.6338 0.3135 0.4111 0.023 Uiso 1 1 calc R . . C3 C 0.7931(3) 0.2907(4) 0.28487(19) 0.0224(6) Uani 1 1 d . . . C4 C 0.7601(3) 0.4483(4) 0.21296(18) 0.0242(6) Uani 1 1 d . . . C5 C 0.6012(2) 0.4589(4) 0.24033(18) 0.0212(6) Uani 1 1 d . . . H5A H 0.5700 0.5894 0.2758 0.025 Uiso 1 1 calc R . . C6 C 0.4888(3) 0.3614(4) 0.15329(19) 0.0238(6) Uani 1 1 d . . . H6A H 0.4774 0.4295 0.0762 0.029 Uiso 1 1 calc R . . C7 C 0.3456(3) 0.3356(4) 0.21539(19) 0.0234(6) Uani 1 1 d . . . H7A H 0.2617 0.2985 0.1593 0.028 Uiso 1 1 calc R . . C8 C 0.3069(3) 0.5128(4) 0.2883(2) 0.0258(6) Uani 1 1 d . . . C9 C 0.3522(3) 0.2529(4) 0.4170(2) 0.0278(6) Uani 1 1 d . . . C10 C 0.3802(2) 0.1608(4) 0.30238(18) 0.0220(5) Uani 1 1 d . . . H10A H 0.3135 0.0421 0.2851 0.026 Uiso 1 1 calc R . . C11 C 0.5368(3) 0.1346(4) 0.15148(19) 0.0265(6) Uani 1 1 d . . . H11A H 0.4631 0.0464 0.1094 0.032 Uiso 1 1 calc R . . H11B H 0.6339 0.1162 0.1201 0.032 Uiso 1 1 calc R . . C12 C 0.9221(3) 0.1619(5) 0.31172(19) 0.0274(6) Uani 1 1 d . . . C13 C 0.9970(3) -0.1507(5) 0.3989(2) 0.0411(8) Uani 1 1 d . . . H13A H 0.9551 -0.2658 0.4392 0.062 Uiso 1 1 calc R . . H13B H 1.0734 -0.0857 0.4497 0.062 Uiso 1 1 calc R . . H13C H 1.0398 -0.2001 0.3290 0.062 Uiso 1 1 calc R . . C14 C 0.8329(3) 0.5772(4) 0.1299(2) 0.0274(6) Uani 1 1 d . . . C15 C 1.0515(3) 0.6614(5) 0.0450(2) 0.0427(7) Uani 1 1 d . . . H15A H 1.1551 0.6216 0.0489 0.064 Uiso 1 1 calc R . . H15B H 1.0436 0.8059 0.0651 0.064 Uiso 1 1 calc R . . H15C H 1.0077 0.6391 -0.0334 0.064 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 O1 0.0313(11) 0.0247(11) 0.0590(12) 0.0038(10) 0.0051(9) 0.0056(11) O2 0.0312(11) 0.0303(11) 0.0322(10) -0.0024(9) 0.0091(7) 0.0053(10) O3 0.0500(13) 0.0570(14) 0.0326(10) 0.0144(11) 0.0146(9) 0.0093(13) O4 0.0200(11) 0.0718(18) 0.0968(16) 0.0476(15) 0.0156(11) 0.0093(13) O5 0.0229(10) 0.0333(12) 0.0503(11) 0.0159(9) 0.0107(8) 0.0071(10) O6 0.0324(12) 0.0705(17) 0.0688(13) 0.0416(13) 0.0096(10) 0.0069(14) O7 0.0270(10) 0.0403(12) 0.0327(9) 0.0129(9) 0.0101(7) -0.0011(10) C1 0.0195(13) 0.0200(14) 0.0313(13) -0.0012(11) 0.0033(10) 0.0035(12) C2 0.0202(13) 0.0190(13) 0.0192(11) 0.0009(10) 0.0034(9) 0.0017(12) C3 0.0189(13) 0.0269(15) 0.0214(12) -0.0023(11) 0.0013(9) -0.0034(13) C4 0.0206(14) 0.0289(15) 0.0228(12) -0.0031(12) 0.0010(10) -0.0036(13) C5 0.0194(13) 0.0204(14) 0.0241(12) 0.0013(11) 0.0032(9) -0.0002(12) C6 0.0240(15) 0.0291(15) 0.0183(11) 0.0009(11) 0.0012(10) 0.0002(13) C7 0.0177(14) 0.0268(16) 0.0252(12) -0.0002(11) -0.0019(10) -0.0006(12) C8 0.0149(13) 0.0243(15) 0.0387(14) 0.0047(12) 0.0052(10) 0.0010(13) C9 0.0202(14) 0.0307(16) 0.0335(14) 0.0036(12) 0.0085(10) -0.0012(13) C10 0.0163(12) 0.0186(13) 0.0311(13) -0.0013(11) 0.0026(9) -0.0016(12) C11 0.0210(13) 0.0314(17) 0.0274(13) -0.0081(12) 0.0029(10) 0.0007(13) C12 0.0226(14) 0.0351(16) 0.0250(12) 0.0030(12) 0.0049(10) 0.0003(14) C13 0.0317(18) 0.0381(18) 0.0536(17) 0.0110(15) 0.0046(14) 0.0139(16) C14 0.0244(15) 0.0308(16) 0.0266(13) 0.0026(12) 0.0000(11) -0.0043(14) C15 0.0346(16) 0.0513(19) 0.0436(16) 0.0185(16) 0.0128(12) -0.0062(18) _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 O1 C8 1.190(3) . ? O2 C8 1.382(3) . ? O2 C9 1.395(3) . ? O3 C9 1.186(3) . ? O4 C12 1.195(3) . ? O5 C12 1.329(3) . ? O5 C13 1.445(3) . ? O6 C14 1.207(3) . ? O7 C14 1.321(3) . ? O7 C15 1.455(3) . ? C1 C2 1.533(3) . ? C1 C11 1.535(3) . ? C1 C10 1.559(3) . ? C2 C3 1.515(3) . ? C2 C5 1.581(3) . ? C3 C4 1.349(4) . ? C3 C12 1.466(4) . ? C4 C14 1.476(3) . ? C4 C5 1.510(3) . ? C5 C6 1.530(3) . ? C6 C7 1.547(3) . ? C6 C11 1.551(4) . ? C7 C8 1.495(4) . ? C7 C10 1.546(3) . ? C9 C10 1.499(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 C8 O2 C9 110.8(2) . . ? C12 O5 C13 117.0(2) . . ? C14 O7 C15 115.9(2) . . ? C2 C1 C11 102.34(19) . . ? C2 C1 C10 107.9(2) . . ? C11 C1 C10 98.59(19) . . ? C3 C2 C1 117.22(19) . . ? C3 C2 C5 85.66(17) . . ? C1 C2 C5 103.94(18) . . ? C4 C3 C12 135.6(2) . . ? C4 C3 C2 94.1(2) . . ? C12 C3 C2 130.3(2) . . ? C3 C4 C14 138.8(2) . . ? C3 C4 C5 94.7(2) . . ? C14 C4 C5 126.6(2) . . ? C4 C5 C6 116.93(19) . . ? C4 C5 C2 85.54(18) . . ? C6 C5 C2 103.0(2) . . ? C5 C6 C7 106.75(17) . . ? C5 C6 C11 103.4(2) . . ? C7 C6 C11 98.7(2) . . ? C8 C7 C10 104.58(18) . . ? C8 C7 C6 114.9(2) . . ? C10 C7 C6 104.17(19) . . ? O1 C8 O2 119.9(2) . . ? O1 C8 C7 129.7(2) . . ? O2 C8 C7 110.4(2) . . ? O3 C9 O2 119.6(2) . . ? O3 C9 C10 130.2(3) . . ? O2 C9 C10 110.2(2) . . ? C9 C10 C7 104.0(2) . . ? C9 C10 C1 116.8(2) . . ? C7 C10 C1 103.71(18) . . ? C1 C11 C6 96.02(19) . . ? O4 C12 O5 123.5(3) . . ? O4 C12 C3 126.8(3) . . ? O5 C12 C3 109.6(2) . . ? O6 C14 O7 124.4(2) . . ? O6 C14 C4 122.0(2) . . ? O7 C14 C4 113.7(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.166 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 908728' ####################################################################### # # 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_compound-7ia #TrackingRef 'compound-7ia.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H21 N O6' _chemical_formula_sum 'C22 H21 N O6' _chemical_formula_weight 395.40 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' _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 8.8506(3) _cell_length_b 9.5121(3) _cell_length_c 22.9522(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.001(3) _cell_angle_gamma 90.00 _cell_volume 1921.71(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6938 _cell_measurement_theta_min 2.7820 _cell_measurement_theta_max 29.2141 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96977 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15519 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3764 _reflns_number_gt 2840 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.0303P] 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 3764 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 O1 O 0.35861(12) 0.18248(13) 0.17990(6) 0.0354(3) Uani 1 1 d . . . O2 O 0.46266(13) 0.64933(12) 0.19341(5) 0.0296(3) Uani 1 1 d . . . O3 O 0.78036(14) 0.67037(13) 0.01123(5) 0.0346(3) Uani 1 1 d . . . O4 O 0.83493(16) 0.49954(15) -0.05055(6) 0.0465(4) Uani 1 1 d . . . O5 O 0.61052(17) 0.20901(15) -0.06844(6) 0.0496(4) Uani 1 1 d . A . O6 O 0.7632(4) 0.1018(3) -0.00048(11) 0.0751(10) Uani 0.710(4) 1 d P A 1 O6A O 0.6512(10) 0.0695(8) 0.0036(3) 0.0751(10) Uani 0.290(4) 1 d P A 2 N1 N 0.38016(13) 0.42152(15) 0.19123(6) 0.0244(3) Uani 1 1 d . . . C1 C 0.67695(16) 0.24833(17) 0.13332(7) 0.0224(4) Uani 1 1 d . . . H1A H 0.6968 0.1452 0.1306 0.027 Uiso 1 1 calc R . . C2 C 0.57880(17) 0.31168(17) 0.08083(7) 0.0223(4) Uani 1 1 d . . . H2A H 0.4679 0.2892 0.0783 0.027 Uiso 1 1 calc R . . C3 C 0.64710(18) 0.31342(19) 0.02341(7) 0.0265(4) Uani 1 1 d . A . C4 C 0.68650(17) 0.44907(18) 0.02719(7) 0.0244(4) Uani 1 1 d . . . C5 C 0.62059(16) 0.47335(17) 0.08463(7) 0.0214(4) Uani 1 1 d . . . H5A H 0.5325 0.5396 0.0830 0.026 Uiso 1 1 calc R . . C6 C 0.73312(16) 0.48203(17) 0.14001(7) 0.0205(3) Uani 1 1 d . . . H6A H 0.7986 0.5680 0.1430 0.025 Uiso 1 1 calc R . . C7 C 0.64360(16) 0.45456(17) 0.19335(7) 0.0212(4) Uani 1 1 d . . . H7A H 0.7083 0.4758 0.2307 0.025 Uiso 1 1 calc R . . C8 C 0.49095(17) 0.52504(17) 0.19285(6) 0.0219(4) Uani 1 1 d . . . C9 C 0.43691(17) 0.28629(18) 0.18636(7) 0.0244(4) Uani 1 1 d . . . C10 C 0.60714(16) 0.29582(17) 0.18903(7) 0.0221(4) Uani 1 1 d . . . H10A H 0.6560 0.2450 0.2242 0.027 Uiso 1 1 calc R . . C11 C 0.81950(16) 0.34217(17) 0.13869(7) 0.0229(4) Uani 1 1 d . . . H11A H 0.8866 0.3247 0.1752 0.027 Uiso 1 1 calc R . . H11B H 0.8780 0.3342 0.1044 0.027 Uiso 1 1 calc R . . C12 C 0.6703(2) 0.1943(2) -0.01591(8) 0.0379(5) Uani 1 1 d . . . C13 C 0.6214(3) 0.0914(2) -0.10808(9) 0.0496(6) Uani 1 1 d . . . H13A H 0.5718 0.1159 -0.1469 0.074 Uiso 1 1 calc R A . H13B H 0.5712 0.0091 -0.0931 0.074 Uiso 1 1 calc R . . H13C H 0.7286 0.0697 -0.1110 0.074 Uiso 1 1 calc R . . C14 C 0.77523(18) 0.53868(19) -0.00898(7) 0.0275(4) Uani 1 1 d . . . C15 C 0.8701(2) 0.7672(2) -0.01940(10) 0.0478(5) Uani 1 1 d . . . H15A H 0.8673 0.8605 -0.0015 0.072 Uiso 1 1 calc R . . H15B H 0.8286 0.7727 -0.0606 0.072 Uiso 1 1 calc R . . H15C H 0.9754 0.7339 -0.0169 0.072 Uiso 1 1 calc R . . C16 C 0.21874(16) 0.4528(2) 0.19083(8) 0.0288(4) Uani 1 1 d . . . H16A H 0.1598 0.3813 0.1667 0.035 Uiso 1 1 calc R . . H16B H 0.1978 0.5454 0.1720 0.035 Uiso 1 1 calc R . . C17 C 0.16439(16) 0.45535(18) 0.25104(8) 0.0237(4) Uani 1 1 d . . . C18 C 0.04167(17) 0.53991(19) 0.26075(8) 0.0300(4) Uani 1 1 d . . . H18A H -0.0023 0.5995 0.2304 0.036 Uiso 1 1 calc R . . C19 C -0.01725(18) 0.5382(2) 0.31437(9) 0.0363(5) Uani 1 1 d . . . H19A H -0.1030 0.5946 0.3202 0.044 Uiso 1 1 calc R . . C20 C 0.0484(2) 0.4547(2) 0.35935(9) 0.0377(5) Uani 1 1 d . . . H20A H 0.0084 0.4539 0.3962 0.045 Uiso 1 1 calc R . . C21 C 0.1719(2) 0.37290(19) 0.35053(9) 0.0347(4) Uani 1 1 d . . . H21A H 0.2185 0.3168 0.3816 0.042 Uiso 1 1 calc R . . C22 C 0.22890(18) 0.37188(18) 0.29637(8) 0.0292(4) Uani 1 1 d . . . H22A H 0.3129 0.3134 0.2904 0.035 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 O1 0.0301(6) 0.0306(8) 0.0473(8) -0.0096(6) 0.0134(6) -0.0125(5) O2 0.0344(6) 0.0262(7) 0.0295(7) -0.0053(5) 0.0093(5) 0.0002(5) O3 0.0463(7) 0.0253(7) 0.0345(7) -0.0001(5) 0.0158(6) 0.0002(6) O4 0.0707(9) 0.0401(8) 0.0329(8) -0.0061(6) 0.0262(7) -0.0045(7) O5 0.0850(10) 0.0334(8) 0.0268(8) -0.0132(6) -0.0114(7) 0.0206(7) O6 0.101(2) 0.0606(16) 0.0542(13) -0.0274(11) -0.0370(17) 0.0555(18) O6A 0.101(2) 0.0606(16) 0.0542(13) -0.0274(11) -0.0370(17) 0.0555(18) N1 0.0188(6) 0.0291(8) 0.0259(8) -0.0041(6) 0.0056(5) -0.0038(6) C1 0.0205(7) 0.0199(9) 0.0271(9) 0.0004(7) 0.0035(6) 0.0020(6) C2 0.0210(7) 0.0226(9) 0.0232(9) -0.0035(7) 0.0016(6) 0.0006(6) C3 0.0288(8) 0.0289(10) 0.0209(9) -0.0019(7) -0.0011(7) 0.0054(7) C4 0.0265(8) 0.0269(10) 0.0193(9) 0.0008(7) 0.0008(6) 0.0061(7) C5 0.0226(7) 0.0216(9) 0.0201(8) -0.0006(7) 0.0025(6) 0.0025(6) C6 0.0195(7) 0.0232(9) 0.0190(8) -0.0009(7) 0.0027(6) -0.0041(6) C7 0.0210(7) 0.0251(9) 0.0176(8) -0.0024(7) 0.0020(6) -0.0041(7) C8 0.0257(8) 0.0254(10) 0.0150(8) -0.0047(7) 0.0048(6) -0.0032(7) C9 0.0243(8) 0.0274(10) 0.0228(9) -0.0025(7) 0.0080(6) -0.0054(7) C10 0.0209(7) 0.0237(9) 0.0219(9) 0.0020(7) 0.0033(6) -0.0015(7) C11 0.0181(7) 0.0283(9) 0.0225(9) 0.0021(7) 0.0034(6) -0.0005(7) C12 0.0573(11) 0.0282(11) 0.0272(11) -0.0029(8) -0.0005(9) 0.0143(9) C13 0.0711(14) 0.0395(13) 0.0355(12) -0.0196(9) -0.0073(10) 0.0167(11) C14 0.0345(9) 0.0290(10) 0.0193(9) -0.0004(7) 0.0049(7) 0.0050(7) C15 0.0632(12) 0.0327(12) 0.0510(13) 0.0023(10) 0.0227(11) -0.0072(10) C16 0.0183(7) 0.0391(11) 0.0291(10) -0.0027(8) 0.0033(7) 0.0001(7) C17 0.0164(7) 0.0244(9) 0.0302(9) -0.0064(7) 0.0023(6) -0.0046(6) C18 0.0203(8) 0.0328(11) 0.0358(11) -0.0069(8) -0.0027(7) 0.0024(7) C19 0.0192(8) 0.0440(12) 0.0466(12) -0.0173(9) 0.0080(8) 0.0027(8) C20 0.0345(9) 0.0451(12) 0.0360(11) -0.0086(9) 0.0155(8) -0.0076(9) C21 0.0423(10) 0.0284(10) 0.0346(11) 0.0008(8) 0.0093(8) -0.0013(8) C22 0.0282(8) 0.0251(10) 0.0356(10) -0.0026(8) 0.0090(7) 0.0041(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.2066(19) . ? O2 C8 1.2089(19) . ? O3 C14 1.335(2) . ? O3 C15 1.446(2) . ? O4 C14 1.197(2) . ? O5 C12 1.272(2) . ? O5 C13 1.452(2) . ? O6 C12 1.231(3) . ? O6A C12 1.286(8) . ? N1 C8 1.387(2) . ? N1 C9 1.390(2) . ? N1 C16 1.4584(19) . ? C1 C2 1.533(2) . ? C1 C11 1.540(2) . ? C1 C10 1.545(2) . ? C2 C3 1.506(2) . ? C2 C5 1.582(2) . ? C3 C4 1.337(2) . ? C3 C12 1.476(2) . ? C4 C14 1.473(2) . ? C4 C5 1.514(2) . ? C5 C6 1.533(2) . ? C6 C11 1.536(2) . ? C6 C7 1.549(2) . ? C7 C8 1.507(2) . ? C7 C10 1.545(2) . ? C9 C10 1.504(2) . ? C16 C17 1.510(2) . ? C17 C22 1.384(2) . ? C17 C18 1.388(2) . ? C18 C19 1.386(3) . ? C19 C20 1.382(3) . ? C20 C21 1.374(3) . ? C21 C22 1.390(2) . ? 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 C14 O3 C15 115.41(14) . . ? C12 O5 C13 117.44(15) . . ? C8 N1 C9 113.49(12) . . ? C8 N1 C16 123.00(14) . . ? C9 N1 C16 123.39(14) . . ? C2 C1 C11 103.14(13) . . ? C2 C1 C10 107.02(12) . . ? C11 C1 C10 99.17(12) . . ? C3 C2 C1 116.46(12) . . ? C3 C2 C5 85.68(12) . . ? C1 C2 C5 103.22(12) . . ? C4 C3 C12 136.76(17) . . ? C4 C3 C2 94.56(13) . . ? C12 C3 C2 128.36(16) . . ? C3 C4 C14 132.28(16) . . ? C3 C4 C5 94.71(13) . . ? C14 C4 C5 132.79(15) . . ? C4 C5 C6 117.01(12) . . ? C4 C5 C2 85.00(12) . . ? C6 C5 C2 103.06(12) . . ? C5 C6 C11 102.62(12) . . ? C5 C6 C7 107.74(11) . . ? C11 C6 C7 99.57(12) . . ? C8 C7 C10 104.66(12) . . ? C8 C7 C6 116.82(13) . . ? C10 C7 C6 103.59(12) . . ? O2 C8 N1 123.22(14) . . ? O2 C8 C7 128.42(14) . . ? N1 C8 C7 108.36(13) . . ? O1 C9 N1 124.03(14) . . ? O1 C9 C10 127.90(16) . . ? N1 C9 C10 108.05(14) . . ? C9 C10 C1 115.74(13) . . ? C9 C10 C7 105.25(13) . . ? C1 C10 C7 103.88(12) . . ? C6 C11 C1 95.64(11) . . ? O6 C12 O5 123.38(19) . . ? O6 C12 O6A 49.3(3) . . ? O5 C12 O6A 112.0(3) . . ? O6 C12 C3 120.26(18) . . ? O5 C12 C3 115.11(16) . . ? O6A C12 C3 117.6(3) . . ? O4 C14 O3 124.54(16) . . ? O4 C14 C4 125.10(17) . . ? O3 C14 C4 110.36(14) . . ? N1 C16 C17 113.77(13) . . ? C22 C17 C18 118.69(16) . . ? C22 C17 C16 122.21(14) . . ? C18 C17 C16 119.06(16) . . ? C19 C18 C17 120.62(17) . . ? C20 C19 C18 120.13(16) . . ? C21 C20 C19 119.65(17) . . ? C20 C21 C22 120.30(18) . . ? C17 C22 C21 120.58(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.438 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 908729'