Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_3709 _database_code_CSD 168097 _journal_coden_Cambridge 182 ############################################################################ _publ_requested_journal 'Chem. Comm.' #_publ_requested_category ?FI ; full inorganic #_publ_requested_category ?FM ; full organometallic #_publ_requested_category ?FO ; full organic #?If CI, CM or CO remember to remove section "..._molecular_graphics" #_publ_requested_category ?CI ; electronic inorganic #_publ_requested_category ?CM ; electronic organometallic #_publ_requested_category ?CO ; electronic organic _publ_section_title ; N-Heterocyclic carbenes coexist with alkenes or C-H acidic sites ; loop_ _publ_author_name _publ_author_address 'Alois Furstner' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'Helga Krause' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'Lutz Ackermann' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'Christian W. Lehmann' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; ############################################################################ _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_compound_source 'see paper' _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 N2' _chemical_formula_weight 254.37 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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5288(4) _cell_length_b 29.1967(15) _cell_length_c 11.0965(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.419(2) _cell_angle_gamma 90.00 _cell_volume 3078.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100 _cell_measurement_reflns_used 32828 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 24.41 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_method none _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_process_details 'XPREP, Siemens (1995)' _exptl_absorpt_correction_T_min 0.55 _exptl_absorpt_correction_T_max 0.85 _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '0.3 mm rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD \w-scan' _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 10536 _diffrn_reflns_av_R_equivalents 0.1482 _diffrn_reflns_av_sigmaI/netI 0.1184 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 22.50 _reflns_number_total 3885 _reflns_number_gt 2615 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect software (Nonius, 1998)' _computing_cell_refinement 'Denzo / Scalepack (Otwinowski 1997)' _computing_data_reduction 'Denzo / Scalepack (Otwinowski 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _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^)+(0.0500P)^2^+4.5935P] 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_number_reflns 3885 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1287 _refine_ls_R_factor_gt 0.0783 _refine_ls_wR_factor_ref 0.2085 _refine_ls_wR_factor_gt 0.1758 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2881(5) 0.15795(15) 0.4126(4) 0.0308(11) Uani 1 1 d . . . N2 N 0.2914(4) 0.20396(12) 0.4366(3) 0.0281(9) Uani 1 1 d . . . C3 C 0.2903(5) 0.21375(16) 0.5580(4) 0.0301(11) Uani 1 1 d . . . H3 H 0.2929 0.2433 0.5942 0.036 Uiso 1 1 calc R . . C4 C 0.2848(4) 0.17356(16) 0.6147(4) 0.0329(12) Uani 1 1 d . . . H4 H 0.2821 0.1686 0.6991 0.039 Uiso 1 1 calc R . . N5 N 0.2839(4) 0.14077(13) 0.5260(3) 0.0310(10) Uani 1 1 d . . . C6 C 0.2774(5) 0.09162(16) 0.5521(4) 0.0352(12) Uani 1 1 d . . . H6A H 0.3405 0.0849 0.6250 0.042 Uiso 1 1 calc R . . H6B H 0.3129 0.0744 0.4838 0.042 Uiso 1 1 calc R . . C7 C 0.1305(5) 0.07468(16) 0.5725(4) 0.0366(12) Uani 1 1 d . . . H7A H 0.0877 0.0952 0.6303 0.044 Uiso 1 1 calc R . . H7B H 0.1369 0.0437 0.6085 0.044 Uiso 1 1 calc R . . C8 C 0.0364(5) 0.07303(17) 0.4544(4) 0.0364(12) Uani 1 1 d . . . H8A H -0.0616 0.0665 0.4728 0.044 Uiso 1 1 calc R . . H8B H 0.0376 0.1033 0.4145 0.044 Uiso 1 1 calc R . . C9 C 0.0829(5) 0.03766(17) 0.3707(5) 0.0402(13) Uani 1 1 d . . . H9 H 0.0749 0.0066 0.3951 0.048 Uiso 1 1 calc R . . C10 C 0.1334(5) 0.0449(2) 0.2677(4) 0.0469(14) Uani 1 1 d . . . H10A H 0.1435 0.0754 0.2394 0.056 Uiso 1 1 calc R . . H10B H 0.1605 0.0198 0.2201 0.056 Uiso 1 1 calc R . . C11 C 0.2972(5) 0.23840(14) 0.3445(4) 0.0290(11) Uani 1 1 d . . . C12 C 0.1751(5) 0.26242(15) 0.3084(4) 0.0320(12) Uani 1 1 d . . . C13 C 0.1845(5) 0.29533(16) 0.2182(4) 0.0369(12) Uani 1 1 d . . . H13 H 0.1022 0.3118 0.1908 0.044 Uiso 1 1 calc R . . C14 C 0.3074(6) 0.30473(16) 0.1679(4) 0.0385(13) Uani 1 1 d . . . C15 C 0.4278(5) 0.27975(16) 0.2065(4) 0.0364(12) Uani 1 1 d . . . H15 H 0.5138 0.2857 0.1713 0.044 Uiso 1 1 calc R . . C16 C 0.4240(5) 0.24648(16) 0.2948(4) 0.0303(11) Uani 1 1 d . . . C21 C 0.0382(5) 0.25293(18) 0.3611(4) 0.0421(13) Uani 1 1 d . . . H21A H 0.0133 0.2206 0.3488 0.063 Uiso 1 1 calc R . . H21B H -0.0356 0.2722 0.3211 0.063 Uiso 1 1 calc R . . H21C H 0.0471 0.2597 0.4478 0.063 Uiso 1 1 calc R . . C22 C 0.3155(7) 0.34090(19) 0.0716(5) 0.0593(17) Uani 1 1 d . . . H22A H 0.3638 0.3284 0.0041 0.089 Uiso 1 1 calc R . . H22B H 0.3678 0.3674 0.1056 0.089 Uiso 1 1 calc R . . H22C H 0.2201 0.3504 0.0428 0.089 Uiso 1 1 calc R . . C23 C 0.5540(5) 0.21944(17) 0.3357(4) 0.0392(13) Uani 1 1 d . . . H23A H 0.5727 0.2225 0.4234 0.059 Uiso 1 1 calc R . . H23B H 0.6345 0.2312 0.2953 0.059 Uiso 1 1 calc R . . H23C H 0.5391 0.1871 0.3150 0.059 Uiso 1 1 calc R . . C1' C 0.3082(5) 0.11825(16) 0.8959(4) 0.0337(12) Uani 1 1 d . . . N2' N 0.3758(4) 0.07872(12) 0.9313(3) 0.0293(9) Uani 1 1 d . . . C3' C 0.4092(5) 0.07756(16) 1.0545(4) 0.0349(12) Uani 1 1 d . . . H3' H 0.4556 0.0534 1.0989 0.042 Uiso 1 1 calc R . . C4' C 0.3639(5) 0.11688(16) 1.0994(4) 0.0324(12) Uani 1 1 d . . . H4' H 0.3712 0.1263 1.1816 0.039 Uiso 1 1 calc R . . N5' N 0.3043(4) 0.14101(13) 1.0016(3) 0.0325(10) Uani 1 1 d . . . C6' C 0.2316(5) 0.18474(16) 1.0123(4) 0.0363(12) Uani 1 1 d . . . H6C H 0.2043 0.1968 0.9305 0.044 Uiso 1 1 calc R . . H6D H 0.2966 0.2070 1.0543 0.044 Uiso 1 1 calc R . . C7' C 0.1015(5) 0.17996(16) 1.0813(4) 0.0353(12) Uani 1 1 d . . . H7C H 0.0592 0.2107 1.0897 0.042 Uiso 1 1 calc R . . H7D H 0.1301 0.1686 1.1636 0.042 Uiso 1 1 calc R . . C8' C -0.0103(5) 0.14799(17) 1.0232(5) 0.0415(13) Uani 1 1 d . . . H8C H -0.0436 0.1602 0.9427 0.050 Uiso 1 1 calc R . . H8D H 0.0323 0.1176 1.0111 0.050 Uiso 1 1 calc R . . C9' C -0.1319(6) 0.14267(18) 1.0972(5) 0.0503(14) Uani 1 1 d . . . H9' H -0.1124 0.1318 1.1775 0.060 Uiso 1 1 calc R . . C10' C -0.2618(7) 0.15132(19) 1.0634(6) 0.0644(17) Uani 1 1 d . . . H10C H -0.2867 0.1622 0.9840 0.077 Uiso 1 1 calc R . . H10D H -0.3326 0.1468 1.1180 0.077 Uiso 1 1 calc R . . C11' C 0.3875(5) 0.04027(15) 0.8519(4) 0.0282(11) Uani 1 1 d . . . C12' C 0.2788(5) 0.00850(16) 0.8456(4) 0.0315(11) Uani 1 1 d . . . C13' C 0.2873(5) -0.02786(16) 0.7643(4) 0.0338(12) Uani 1 1 d . . . H13' H 0.2146 -0.0502 0.7590 0.041 Uiso 1 1 calc R . . C14' C 0.3979(5) -0.03242(15) 0.6913(4) 0.0306(11) Uani 1 1 d . . . C15' C 0.5042(5) 0.00070(16) 0.7013(4) 0.0326(12) Uani 1 1 d . . . H15' H 0.5802 -0.0018 0.6512 0.039 Uiso 1 1 calc R . . C16' C 0.5027(5) 0.03691(15) 0.7812(4) 0.0289(11) Uani 1 1 d . . . C21' C 0.1566(5) 0.01264(19) 0.9211(4) 0.0453(14) Uani 1 1 d . . . H21D H 0.1908 0.0160 1.0062 0.068 Uiso 1 1 calc R . . H21E H 0.0980 -0.0149 0.9113 0.068 Uiso 1 1 calc R . . H21F H 0.1006 0.0396 0.8955 0.068 Uiso 1 1 calc R . . C22' C 0.4033(5) -0.07234(17) 0.6069(4) 0.0397(13) Uani 1 1 d . . . H22D H 0.4093 -0.0612 0.5242 0.060 Uiso 1 1 calc R . . H22E H 0.3179 -0.0908 0.6107 0.060 Uiso 1 1 calc R . . H22F H 0.4860 -0.0911 0.6306 0.060 Uiso 1 1 calc R . . C23' C 0.6184(5) 0.07160(17) 0.7920(5) 0.0445(13) Uani 1 1 d . . . H23D H 0.6914 0.0631 0.7386 0.067 Uiso 1 1 calc R . . H23E H 0.6592 0.0726 0.8758 0.067 Uiso 1 1 calc R . . H23F H 0.5804 0.1018 0.7688 0.067 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 C1 0.023(3) 0.034(3) 0.035(3) 0.002(2) -0.002(2) 0.000(2) N2 0.022(2) 0.033(2) 0.028(2) 0.0013(18) -0.0030(17) -0.0035(16) C3 0.027(3) 0.035(3) 0.027(3) -0.002(2) -0.001(2) -0.004(2) C4 0.028(3) 0.044(3) 0.026(3) -0.001(2) -0.004(2) -0.007(2) N5 0.022(2) 0.037(2) 0.033(2) 0.0088(19) -0.0047(17) -0.0003(17) C6 0.033(3) 0.034(3) 0.037(3) 0.007(2) -0.005(2) 0.003(2) C7 0.035(3) 0.038(3) 0.037(3) 0.008(2) 0.004(2) 0.001(2) C8 0.025(3) 0.043(3) 0.042(3) 0.001(2) 0.004(2) -0.001(2) C9 0.033(3) 0.038(3) 0.050(3) -0.001(3) 0.004(3) -0.005(2) C10 0.040(3) 0.063(4) 0.037(3) -0.004(3) 0.000(3) 0.001(3) C11 0.032(3) 0.026(2) 0.027(3) -0.003(2) -0.004(2) -0.001(2) C12 0.032(3) 0.032(3) 0.031(3) 0.002(2) -0.001(2) 0.000(2) C13 0.038(3) 0.037(3) 0.035(3) 0.000(2) -0.004(2) 0.003(2) C14 0.056(4) 0.031(3) 0.029(3) 0.000(2) 0.000(3) -0.010(2) C15 0.040(3) 0.038(3) 0.032(3) -0.002(2) 0.007(2) -0.013(2) C16 0.026(3) 0.037(3) 0.028(3) -0.006(2) 0.005(2) -0.007(2) C21 0.031(3) 0.053(3) 0.042(3) 0.003(3) 0.000(2) 0.007(2) C22 0.082(5) 0.049(3) 0.045(3) 0.016(3) -0.006(3) -0.017(3) C23 0.027(3) 0.046(3) 0.044(3) -0.001(2) 0.003(2) -0.002(2) C1' 0.032(3) 0.037(3) 0.032(3) 0.002(2) 0.000(2) 0.001(2) N2' 0.026(2) 0.034(2) 0.026(2) 0.0028(18) -0.0037(17) 0.0012(18) C3' 0.031(3) 0.039(3) 0.033(3) 0.005(2) -0.006(2) 0.000(2) C4' 0.031(3) 0.042(3) 0.023(3) 0.000(2) -0.005(2) -0.003(2) N5' 0.032(2) 0.035(2) 0.031(2) 0.0009(19) 0.0019(18) -0.0037(18) C6' 0.037(3) 0.033(3) 0.040(3) -0.006(2) 0.003(2) 0.001(2) C7' 0.032(3) 0.038(3) 0.036(3) 0.000(2) 0.005(2) 0.004(2) C8' 0.040(3) 0.035(3) 0.048(3) 0.000(2) 0.000(3) -0.001(2) C9' 0.038(4) 0.050(3) 0.063(4) 0.008(3) 0.004(3) -0.001(3) C10' 0.054(4) 0.055(4) 0.085(5) 0.002(3) 0.007(3) -0.008(3) C11' 0.029(3) 0.032(3) 0.023(2) 0.002(2) -0.008(2) 0.005(2) C12' 0.023(3) 0.042(3) 0.029(3) -0.001(2) -0.003(2) 0.003(2) C13' 0.026(3) 0.041(3) 0.033(3) -0.002(2) -0.006(2) -0.002(2) C14' 0.028(3) 0.035(3) 0.028(3) 0.000(2) -0.004(2) 0.008(2) C15' 0.027(3) 0.041(3) 0.029(3) 0.003(2) 0.003(2) 0.005(2) C16' 0.025(3) 0.032(3) 0.029(3) 0.007(2) 0.001(2) 0.003(2) C21' 0.030(3) 0.060(3) 0.047(3) -0.015(3) 0.008(2) -0.010(3) C22' 0.032(3) 0.047(3) 0.040(3) -0.001(3) 0.003(2) 0.005(2) C23' 0.029(3) 0.042(3) 0.063(4) 0.006(3) 0.009(3) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N5 1.358(6) . ? C1 N2 1.370(6) . ? N2 C3 1.378(6) . ? N2 C11 1.438(6) . ? C3 C4 1.334(6) . ? C3 H3 0.9500 . ? C4 N5 1.373(6) . ? C4 H4 0.9500 . ? N5 C6 1.466(6) . ? C6 C7 1.518(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.530(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.479(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.292(7) . ? C9 H9 0.9500 . ? C10 H10A 0.9500 . ? C10 H10B 0.9500 . ? C11 C16 1.386(6) . ? C11 C12 1.391(6) . ? C12 C13 1.396(6) . ? C12 C21 1.496(7) . ? C13 C14 1.364(7) . ? C13 H13 0.9500 . ? C14 C15 1.398(7) . ? C14 C22 1.508(7) . ? C15 C16 1.382(6) . ? C15 H15 0.9500 . ? C16 C23 1.509(6) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C1' N5' 1.351(6) . ? C1' N2' 1.365(6) . ? N2' C3' 1.380(6) . ? N2' C11' 1.437(5) . ? C3' C4' 1.336(6) . ? C3' H3' 0.9500 . ? C4' N5' 1.379(5) . ? C4' H4' 0.9500 . ? N5' C6' 1.462(6) . ? C6' C7' 1.513(7) . ? C6' H6C 0.9900 . ? C6' H6D 0.9900 . ? C7' C8' 1.521(6) . ? C7' H7C 0.9900 . ? C7' H7D 0.9900 . ? C8' C9' 1.480(7) . ? C8' H8C 0.9900 . ? C8' H8D 0.9900 . ? C9' C10' 1.291(7) . ? C9' H9' 0.9500 . ? C10' H10C 0.9500 . ? C10' H10D 0.9500 . ? C11' C12' 1.388(6) . ? C11' C16' 1.402(6) . ? C12' C13' 1.399(6) . ? C12' C21' 1.492(7) . ? C13' C14' 1.384(7) . ? C13' H13' 0.9500 . ? C14' C15' 1.398(6) . ? C14' C22' 1.499(6) . ? C15' C16' 1.380(6) . ? C15' H15' 0.9500 . ? C16' C23' 1.495(6) . ? C21' H21D 0.9800 . ? C21' H21E 0.9800 . ? C21' H21F 0.9800 . ? C22' H22D 0.9800 . ? C22' H22E 0.9800 . ? C22' H22F 0.9800 . ? C23' H23D 0.9800 . ? C23' H23E 0.9800 . ? C23' H23F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 C1 N2 100.6(4) . . ? C1 N2 C3 113.1(4) . . ? C1 N2 C11 123.3(4) . . ? C3 N2 C11 123.6(4) . . ? C4 C3 N2 106.4(4) . . ? C4 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? C3 C4 N5 105.9(4) . . ? C3 C4 H4 127.1 . . ? N5 C4 H4 127.1 . . ? C1 N5 C4 114.1(4) . . ? C1 N5 C6 123.3(4) . . ? C4 N5 C6 122.6(4) . . ? N5 C6 C7 113.7(4) . . ? N5 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? N5 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 C8 111.6(4) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C7 112.0(4) . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 126.2(5) . . ? C10 C9 H9 116.9 . . ? C8 C9 H9 116.9 . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? C16 C11 C12 122.4(4) . . ? C16 C11 N2 119.0(4) . . ? C12 C11 N2 118.7(4) . . ? C11 C12 C13 117.1(5) . . ? C11 C12 C21 122.0(4) . . ? C13 C12 C21 120.9(4) . . ? C14 C13 C12 122.5(5) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 118.7(4) . . ? C13 C14 C22 121.5(5) . . ? C15 C14 C22 119.8(5) . . ? C16 C15 C14 121.2(5) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 118.2(4) . . ? C15 C16 C23 121.0(4) . . ? C11 C16 C23 120.7(4) . . ? C12 C21 H21A 109.5 . . ? C12 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C12 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C22 H22A 109.5 . . ? C14 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C14 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C16 C23 H23A 109.5 . . ? C16 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C16 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N5' C1' N2' 102.1(4) . . ? C1' N2' C3' 112.0(4) . . ? C1' N2' C11' 122.7(4) . . ? C3' N2' C11' 124.4(4) . . ? C4' C3' N2' 107.0(4) . . ? C4' C3' H3' 126.5 . . ? N2' C3' H3' 126.5 . . ? C3' C4' N5' 105.7(4) . . ? C3' C4' H4' 127.1 . . ? N5' C4' H4' 127.1 . . ? C1' N5' C4' 113.2(4) . . ? C1' N5' C6' 123.0(4) . . ? C4' N5' C6' 123.4(4) . . ? N5' C6' C7' 111.9(4) . . ? N5' C6' H6C 109.2 . . ? C7' C6' H6C 109.2 . . ? N5' C6' H6D 109.2 . . ? C7' C6' H6D 109.2 . . ? H6C C6' H6D 107.9 . . ? C6' C7' C8' 114.6(4) . . ? C6' C7' H7C 108.6 . . ? C8' C7' H7C 108.6 . . ? C6' C7' H7D 108.6 . . ? C8' C7' H7D 108.6 . . ? H7C C7' H7D 107.6 . . ? C9' C8' C7' 112.4(4) . . ? C9' C8' H8C 109.1 . . ? C7' C8' H8C 109.1 . . ? C9' C8' H8D 109.1 . . ? C7' C8' H8D 109.1 . . ? H8C C8' H8D 107.9 . . ? C10' C9' C8' 126.4(6) . . ? C10' C9' H9' 116.8 . . ? C8' C9' H9' 116.8 . . ? C9' C10' H10C 120.0 . . ? C9' C10' H10D 120.0 . . ? H10C C10' H10D 120.0 . . ? C12' C11' C16' 122.6(4) . . ? C12' C11' N2' 117.4(4) . . ? C16' C11' N2' 120.0(4) . . ? C11' C12' C13' 117.4(4) . . ? C11' C12' C21' 121.9(4) . . ? C13' C12' C21' 120.7(4) . . ? C14' C13' C12' 122.3(4) . . ? C14' C13' H13' 118.8 . . ? C12' C13' H13' 118.8 . . ? C13' C14' C15' 117.8(4) . . ? C13' C14' C22' 120.3(4) . . ? C15' C14' C22' 121.9(4) . . ? C16' C15' C14' 122.5(4) . . ? C16' C15' H15' 118.7 . . ? C14' C15' H15' 118.7 . . ? C15' C16' C11' 117.4(4) . . ? C15' C16' C23' 121.8(4) . . ? C11' C16' C23' 120.8(4) . . ? C12' C21' H21D 109.5 . . ? C12' C21' H21E 109.5 . . ? H21D C21' H21E 109.5 . . ? C12' C21' H21F 109.5 . . ? H21D C21' H21F 109.5 . . ? H21E C21' H21F 109.5 . . ? C14' C22' H22D 109.5 . . ? C14' C22' H22E 109.5 . . ? H22D C22' H22E 109.5 . . ? C14' C22' H22F 109.5 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 109.5 . . ? C16' C23' H23D 109.5 . . ? C16' C23' H23E 109.5 . . ? H23D C23' H23E 109.5 . . ? C16' C23' H23F 109.5 . . ? H23D C23' H23F 109.5 . . ? H23E C23' H23F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.252 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.056 data_3792 _database_code_CSD 168098 _journal_coden_Cambridge 182 ############################################################################ _publ_requested_journal 'Chem. Comm.' #_publ_requested_category ?FI ; full inorganic #_publ_requested_category ?FM ; full organometallic #_publ_requested_category ?FO ; full organic #?If CI, CM or CO remember to remove section "..._molecular_graphics" #_publ_requested_category ?CI ; electronic inorganic #_publ_requested_category ?CM ; electronic organometallic #_publ_requested_category ?CO ; electronic organic _publ_section_title ; N-Heterocyclic carbenes coexist with alkenes or C-H acidic sites ; loop_ _publ_author_name _publ_author_address 'Alois Furstner' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'Lutz Ackermann' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'Helga Krause' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'Christian W. Lehmann' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; ############################################################################ _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_compound_source 'see paper' _chemical_formula_moiety ? _chemical_formula_sum 'C42 H61 Cl2 N2 O2 P Ru' _chemical_formula_weight 828.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.4060(2) _cell_length_b 10.28100(10) _cell_length_c 23.6677(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.6730(10) _cell_angle_gamma 90.00 _cell_volume 4206.67(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 37093 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.14 _exptl_crystal_description block _exptl_crystal_colour red-brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method none _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 0.573 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none _exptl_absorpt_correction_T_min 0 _exptl_absorpt_correction_T_max 0 _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '0.3 mm focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD \w-scan' _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 44732 _diffrn_reflns_av_R_equivalents 0.0746 _diffrn_reflns_av_sigmaI/netI 0.0854 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 33.14 _reflns_number_total 15979 _reflns_number_gt 11340 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect software (Nonius, 1998)' _computing_cell_refinement 'Denzo / Scalepack (Otwinowski 1997)' _computing_data_reduction 'Denzo / Scalepack (Otwinowski 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _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^)+(0.0374P)^2^+3.4289P] 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_number_reflns 15979 _refine_ls_number_parameters 456 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1127 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.008 _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 0.736802(9) 0.507362(15) 0.586482(7) 0.01233(4) Uani 1 1 d . . . P1 P 0.75170(3) 0.48343(5) 0.68870(2) 0.01308(10) Uani 1 1 d . . . Cl1 Cl 0.63368(3) 0.35030(5) 0.57883(2) 0.01578(10) Uani 1 1 d . . . Cl2 Cl 0.80659(3) 0.70843(5) 0.59521(2) 0.01958(11) Uani 1 1 d . . . N1 N 0.70805(10) 0.51964(17) 0.45158(8) 0.0160(3) Uani 1 1 d . . . N2 N 0.63069(10) 0.63660(17) 0.49412(8) 0.0171(4) Uani 1 1 d . . . O1 O 0.61532(12) 0.90534(17) 0.49367(8) 0.0346(5) Uani 1 1 d . . . O2 O 0.57829(11) 0.89987(15) 0.58158(8) 0.0281(4) Uani 1 1 d . . . C1 C 0.69299(12) 0.5573(2) 0.50447(9) 0.0149(4) Uani 1 1 d . . . C2 C 0.65510(13) 0.5749(2) 0.40964(10) 0.0213(4) Uani 1 1 d . . . H2 H 0.6538 0.5638 0.3705 0.026 Uiso 1 1 calc R . . C3 C 0.60613(13) 0.6477(2) 0.43665(10) 0.0217(5) Uani 1 1 d . . . H3 H 0.5642 0.6958 0.4199 0.026 Uiso 1 1 calc R . . C4 C 0.59576(12) 0.6995(2) 0.54039(10) 0.0174(4) Uani 1 1 d . . . H4 H 0.6273 0.6768 0.5760 0.021 Uiso 1 1 calc R . . C5 C 0.51387(13) 0.6509(2) 0.54478(11) 0.0225(5) Uani 1 1 d . . . H5A H 0.4812 0.6725 0.5106 0.034 Uiso 1 1 calc R . . H5B H 0.4942 0.6914 0.5767 0.034 Uiso 1 1 calc R . . H5C H 0.5147 0.5583 0.5499 0.034 Uiso 1 1 calc R . . C6 C 0.59863(13) 0.8470(2) 0.53430(11) 0.0209(4) Uani 1 1 d . . . C7 C 0.57887(17) 1.0416(2) 0.58407(12) 0.0301(6) Uani 1 1 d . . . H7A H 0.5549 1.0780 0.5485 0.036 Uiso 1 1 calc R . . H7B H 0.6315 1.0738 0.5912 0.036 Uiso 1 1 calc R . . C8 C 0.53387(15) 1.0781(2) 0.63188(12) 0.0277(5) Uani 1 1 d . . . H8A H 0.4806 1.0545 0.6223 0.042 Uiso 1 1 calc R . . H8B H 0.5376 1.1703 0.6382 0.042 Uiso 1 1 calc R . . H8C H 0.5545 1.0331 0.6658 0.042 Uiso 1 1 calc R . . C9 C 0.82415(12) 0.4206(2) 0.57055(9) 0.0161(4) Uani 1 1 d . . . H9 H 0.8650 0.4767 0.5663 0.019 Uiso 1 1 calc R . . C10 C 0.84460(12) 0.2841(2) 0.56297(10) 0.0169(4) Uani 1 1 d . . . C11 C 0.79305(13) 0.1797(2) 0.56509(11) 0.0224(5) Uani 1 1 d . . . H11 H 0.7425 0.1958 0.5723 0.027 Uiso 1 1 calc R . . C12 C 0.81646(15) 0.0532(2) 0.55662(12) 0.0259(5) Uani 1 1 d . . . H12 H 0.7814 -0.0148 0.5577 0.031 Uiso 1 1 calc R . . C13 C 0.89204(15) 0.0274(2) 0.54648(12) 0.0271(5) Uani 1 1 d . . . H13 H 0.9076 -0.0577 0.5409 0.032 Uiso 1 1 calc R . . C14 C 0.94399(14) 0.1285(2) 0.54472(11) 0.0249(5) Uani 1 1 d . . . H14 H 0.9947 0.1114 0.5383 0.030 Uiso 1 1 calc R . . C15 C 0.92035(13) 0.2560(2) 0.55256(10) 0.0196(4) Uani 1 1 d . . . H15 H 0.9555 0.3236 0.5508 0.023 Uiso 1 1 calc R . . C21 C 0.77267(12) 0.4420(2) 0.43868(9) 0.0155(4) Uani 1 1 d . . . C22 C 0.76250(12) 0.3083(2) 0.42974(9) 0.0165(4) Uani 1 1 d . . . C23 C 0.82605(13) 0.2379(2) 0.41597(9) 0.0179(4) Uani 1 1 d . . . H23 H 0.8209 0.1487 0.4100 0.021 Uiso 1 1 calc R . . C24 C 0.89694(13) 0.2965(2) 0.41082(10) 0.0195(4) Uani 1 1 d . . . C25 C 0.90417(13) 0.4297(2) 0.41983(10) 0.0203(4) Uani 1 1 d . . . H25 H 0.9514 0.4696 0.4166 0.024 Uiso 1 1 calc R . . C26 C 0.84236(13) 0.5048(2) 0.43355(9) 0.0184(4) Uani 1 1 d . . . C27 C 0.68621(13) 0.2428(2) 0.43541(11) 0.0217(5) Uani 1 1 d . . . H27A H 0.6685 0.2677 0.4708 0.033 Uiso 1 1 calc R . . H27B H 0.6928 0.1501 0.4346 0.033 Uiso 1 1 calc R . . H27C H 0.6488 0.2689 0.4045 0.033 Uiso 1 1 calc R . . C28 C 0.96402(14) 0.2167(3) 0.39582(12) 0.0279(5) Uani 1 1 d . . . H28A H 0.9613 0.2089 0.3552 0.042 Uiso 1 1 calc R . . H28B H 0.9620 0.1318 0.4124 0.042 Uiso 1 1 calc R . . H28C H 1.0116 0.2585 0.4103 0.042 Uiso 1 1 calc R . . C29 C 0.85086(15) 0.6496(2) 0.44370(12) 0.0259(5) Uani 1 1 d . . . H29A H 0.8120 0.6950 0.4191 0.039 Uiso 1 1 calc R . . H29B H 0.9012 0.6770 0.4358 0.039 Uiso 1 1 calc R . . H29C H 0.8447 0.6686 0.4826 0.039 Uiso 1 1 calc R . . C31 C 0.67283(12) 0.5720(2) 0.71940(9) 0.0155(4) Uani 1 1 d . . . H31 H 0.6770 0.5494 0.7599 0.019 Uiso 1 1 calc R . . C32 C 0.59256(12) 0.5262(2) 0.69266(10) 0.0166(4) Uani 1 1 d . . . H32A H 0.5856 0.5489 0.6526 0.020 Uiso 1 1 calc R . . H32B H 0.5892 0.4323 0.6957 0.020 Uiso 1 1 calc R . . C33 C 0.52860(13) 0.5889(2) 0.72241(11) 0.0245(5) Uani 1 1 d . . . H33A H 0.5329 0.5596 0.7616 0.029 Uiso 1 1 calc R . . H33B H 0.4786 0.5613 0.7038 0.029 Uiso 1 1 calc R . . C34 C 0.53342(14) 0.7370(2) 0.72109(12) 0.0274(5) Uani 1 1 d . . . H34A H 0.4947 0.7737 0.7428 0.033 Uiso 1 1 calc R . . H34B H 0.5227 0.7672 0.6821 0.033 Uiso 1 1 calc R . . C35 C 0.61367(14) 0.7835(2) 0.74612(12) 0.0258(5) Uani 1 1 d . . . H35A H 0.6218 0.7620 0.7863 0.031 Uiso 1 1 calc R . . H35B H 0.6165 0.8773 0.7426 0.031 Uiso 1 1 calc R . . C36 C 0.67779(13) 0.7208(2) 0.71586(11) 0.0212(5) Uani 1 1 d . . . H36A H 0.6724 0.7476 0.6763 0.025 Uiso 1 1 calc R . . H36B H 0.7279 0.7498 0.7336 0.025 Uiso 1 1 calc R . . C41 C 0.83970(12) 0.5581(2) 0.72692(10) 0.0172(4) Uani 1 1 d . . . H41 H 0.8348 0.6513 0.7185 0.021 Uiso 1 1 calc R . . C42 C 0.84601(13) 0.5489(2) 0.79190(10) 0.0217(5) Uani 1 1 d . . . H42A H 0.8543 0.4590 0.8035 0.026 Uiso 1 1 calc R . . H42B H 0.7980 0.5780 0.8048 0.026 Uiso 1 1 calc R . . C43 C 0.91338(14) 0.6331(3) 0.81951(11) 0.0282(5) Uani 1 1 d . . . H43A H 0.9022 0.7240 0.8113 0.034 Uiso 1 1 calc R . . H43B H 0.9183 0.6218 0.8605 0.034 Uiso 1 1 calc R . . C44 C 0.98957(14) 0.5966(3) 0.79759(11) 0.0281(5) Uani 1 1 d . . . H44A H 1.0040 0.5090 0.8098 0.034 Uiso 1 1 calc R . . H44B H 1.0300 0.6553 0.8136 0.034 Uiso 1 1 calc R . . C45 C 0.98249(13) 0.6039(3) 0.73291(11) 0.0249(5) Uani 1 1 d . . . H45A H 1.0308 0.5764 0.7199 0.030 Uiso 1 1 calc R . . H45B H 0.9730 0.6933 0.7209 0.030 Uiso 1 1 calc R . . C46 C 0.91643(12) 0.5174(2) 0.70567(10) 0.0200(4) Uani 1 1 d . . . H46A H 0.9274 0.4271 0.7155 0.024 Uiso 1 1 calc R . . H46B H 0.9122 0.5255 0.6646 0.024 Uiso 1 1 calc R . . C51 C 0.73965(12) 0.3135(2) 0.71349(9) 0.0147(4) Uani 1 1 d . . . H51 H 0.7008 0.2745 0.6852 0.018 Uiso 1 1 calc R . . C52 C 0.70857(12) 0.2928(2) 0.77100(9) 0.0174(4) Uani 1 1 d . . . H52A H 0.7463 0.3231 0.8015 0.021 Uiso 1 1 calc R . . H52B H 0.6614 0.3425 0.7721 0.021 Uiso 1 1 calc R . . C53 C 0.69214(13) 0.1477(2) 0.77928(10) 0.0192(4) Uani 1 1 d . . . H53A H 0.6742 0.1351 0.8162 0.023 Uiso 1 1 calc R . . H53B H 0.6512 0.1199 0.7505 0.023 Uiso 1 1 calc R . . C54 C 0.76338(13) 0.0640(2) 0.77543(10) 0.0210(4) Uani 1 1 d . . . H54A H 0.7499 -0.0270 0.7787 0.025 Uiso 1 1 calc R . . H54B H 0.8026 0.0851 0.8066 0.025 Uiso 1 1 calc R . . C55 C 0.79571(13) 0.0866(2) 0.71907(10) 0.0200(4) Uani 1 1 d . . . H55A H 0.7585 0.0572 0.6880 0.024 Uiso 1 1 calc R . . H55B H 0.8428 0.0365 0.7183 0.024 Uiso 1 1 calc R . . C56 C 0.81312(12) 0.2317(2) 0.71120(10) 0.0176(4) Uani 1 1 d . . . H56A H 0.8527 0.2598 0.7409 0.021 Uiso 1 1 calc R . . H56B H 0.8326 0.2446 0.6749 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 0.01356(7) 0.01040(7) 0.01335(8) 0.00045(6) 0.00298(5) 0.00056(6) P1 0.0119(2) 0.0134(2) 0.0141(2) 0.00078(19) 0.00266(18) 0.00032(18) Cl1 0.0152(2) 0.0142(2) 0.0179(2) -0.00011(18) 0.00149(18 -0.00062(17) Cl2 0.0233(2) 0.0133(2) 0.0223(3) 0.00029(19) 0.0034(2) -0.00414(19) N1 0.0176(8) 0.0160(8) 0.0146(8) 0.0013(6) 0.0025(7) 0.0035(7) N2 0.0177(8) 0.0153(8) 0.0185(9) -0.0007(7) 0.0028(7) 0.0043(7) O1 0.0596(13) 0.0177(8) 0.0297(11) 0.0017(7) 0.0185(9) 0.0031(8) O2 0.0450(11) 0.0113(7) 0.0310(10) -0.0029(7) 0.0168(8) 0.0000(7) C1 0.0172(9) 0.0107(9) 0.0175(10) -0.0010(7) 0.0045(8) -0.0006(7) C2 0.0257(11) 0.0216(11) 0.0155(11) 0.0001(8) -0.0020(9) 0.0054(9) C3 0.0228(11) 0.0206(11) 0.0205(11) 0.0015(9) -0.0029(9) 0.0072(9) C4 0.0178(10) 0.0149(9) 0.0193(11) -0.0002(8) 0.0018(8) 0.0031(8) C5 0.0189(10) 0.0225(11) 0.0261(12) -0.0038(9) 0.0022(9) -0.0014(9) C6 0.0219(11) 0.0151(10) 0.0259(12) 0.0006(9) 0.0043(9) 0.0030(8) C7 0.0450(16) 0.0116(10) 0.0363(15) -0.0040(10) 0.0162(12) -0.0006(10) C8 0.0339(13) 0.0199(11) 0.0306(14) -0.0027(10) 0.0086(11) 0.0032(10) C9 0.0163(9) 0.0165(10) 0.0156(10) 0.0000(8) 0.0029(8) -0.0002(8) C10 0.0180(10) 0.0156(10) 0.0172(10) 0.0019(8) 0.0022(8) 0.0035(8) C11 0.0187(10) 0.0179(10) 0.0314(13) 0.0024(9) 0.0064(9) 0.0031(8) C12 0.0267(12) 0.0175(11) 0.0340(14) 0.0012(10) 0.0052(10) 0.0006(9) C13 0.0303(12) 0.0218(12) 0.0289(13) -0.0002(9) 0.0021(10) 0.0108(10) C14 0.0196(10) 0.0287(12) 0.0262(13) -0.0011(10) 0.0020(9) 0.0106(9) C15 0.0166(10) 0.0211(10) 0.0207(11) -0.0006(8) 0.0009(8) 0.0025(8) C21 0.0176(9) 0.0162(9) 0.0129(10) 0.0001(7) 0.0022(8) 0.0040(8) C22 0.0169(9) 0.0184(10) 0.0143(10) -0.0011(8) 0.0019(8) 0.0016(8) C23 0.0213(10) 0.0171(10) 0.0157(10) -0.0012(8) 0.0042(8) 0.0032(8) C24 0.0178(10) 0.0244(11) 0.0169(11) 0.0017(8) 0.0044(8) 0.0050(8) C25 0.0165(10) 0.0250(11) 0.0199(11) 0.0022(9) 0.0038(8) -0.0008(8) C26 0.0204(10) 0.0187(10) 0.0164(10) 0.0005(8) 0.0039(8) -0.0006(8) C27 0.0199(10) 0.0212(11) 0.0243(12) -0.0029(9) 0.0039(9) -0.0004(9) C28 0.0244(12) 0.0297(13) 0.0313(14) 0.0021(10) 0.0102(10) 0.0089(10) C29 0.0268(12) 0.0210(11) 0.0312(14) 0.0004(10) 0.0088(10) -0.0033(9) C31 0.0150(9) 0.0158(10) 0.0160(10) -0.0011(7) 0.0034(8) 0.0016(7) C32 0.0142(9) 0.0182(10) 0.0176(10) -0.0021(8) 0.0030(8) 0.0012(7) C33 0.0159(10) 0.0260(12) 0.0325(14) -0.0064(10) 0.0069(9) 0.0002(9) C34 0.0215(11) 0.0233(12) 0.0382(15) -0.0060(10) 0.0064(10) 0.0072(9) C35 0.0250(12) 0.0198(11) 0.0330(14) -0.0088(10) 0.0048(10) 0.0020(9) C36 0.0193(10) 0.0159(10) 0.0287(13) -0.0021(9) 0.0041(9) 0.0007(8) C41 0.0149(9) 0.0186(10) 0.0181(11) 0.0002(8) 0.0019(8) -0.0035(8) C42 0.0190(10) 0.0285(12) 0.0176(11) -0.0040(9) 0.0021(8) -0.0038(9) C43 0.0240(12) 0.0362(14) 0.0240(13) -0.0047(10) 0.0008(10) -0.0082(10) C44 0.0194(11) 0.0400(15) 0.0240(13) -0.0008(11) -0.0005(9) -0.0108(10) C45 0.0172(10) 0.0329(13) 0.0246(13) 0.0022(10) 0.0028(9) -0.0078(9) C46 0.0142(9) 0.0251(11) 0.0207(11) -0.0004(9) 0.0025(8) -0.0036(8) C51 0.0140(9) 0.0142(9) 0.0161(10) 0.0014(7) 0.0018(7) -0.0006(7) C52 0.0170(9) 0.0183(10) 0.0171(10) 0.0034(8) 0.0031(8) 0.0007(8) C53 0.0188(10) 0.0198(10) 0.0197(11) 0.0035(8) 0.0043(8) -0.0048(8) C54 0.0230(11) 0.0153(10) 0.0239(12) 0.0049(9) -0.0010(9) -0.0027(8) C55 0.0194(10) 0.0176(10) 0.0227(12) 0.0014(8) 0.0013(9) 0.0031(8) C56 0.0139(9) 0.0160(10) 0.0229(11) 0.0022(8) 0.0026(8) 0.0013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru1 C9 1.839(2) . ? Ru1 C1 2.066(2) . ? Ru1 Cl2 2.3944(5) . ? Ru1 Cl1 2.4056(5) . ? Ru1 P1 2.4156(6) . ? P1 C41 1.852(2) . ? P1 C31 1.864(2) . ? P1 C51 1.863(2) . ? N1 C1 1.364(3) . ? N1 C2 1.395(3) . ? N1 C21 1.441(3) . ? N2 C1 1.356(3) . ? N2 C3 1.382(3) . ? N2 C4 1.464(3) . ? O1 C6 1.198(3) . ? O2 C6 1.329(3) . ? O2 C7 1.458(3) . ? C2 C3 1.350(3) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C6 1.524(3) . ? C4 C5 1.526(3) . ? C4 H4 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C7 C8 1.497(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.465(3) . ? C9 H9 0.9300 . ? C10 C15 1.399(3) . ? C10 C11 1.403(3) . ? C11 C12 1.385(3) . ? C11 H11 0.9300 . ? C12 C13 1.390(4) . ? C12 H12 0.9300 . ? C13 C14 1.381(4) . ? C13 H13 0.9300 . ? C14 C15 1.393(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C21 C26 1.392(3) . ? C21 C22 1.399(3) . ? C22 C23 1.392(3) . ? C22 C27 1.509(3) . ? C23 C24 1.391(3) . ? C23 H23 0.9300 . ? C24 C25 1.389(3) . ? C24 C28 1.503(3) . ? C25 C26 1.393(3) . ? C25 H25 0.9300 . ? C26 C29 1.512(3) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C31 C36 1.535(3) . ? C31 C32 1.539(3) . ? C31 H31 0.9800 . ? C32 C33 1.527(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.526(3) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.529(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.536(3) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C41 C42 1.532(3) . ? C41 C46 1.539(3) . ? C41 H41 0.9800 . ? C42 C43 1.541(3) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 C44 1.526(4) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.523(4) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C46 1.535(3) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C51 C52 1.537(3) . ? C51 C56 1.537(3) . ? C51 H51 0.9800 . ? C52 C53 1.536(3) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 C54 1.521(3) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 C55 1.525(3) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C55 C56 1.537(3) . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 Ru1 C1 98.72(9) . . ? C9 Ru1 Cl2 90.75(7) . . ? C1 Ru1 Cl2 89.69(6) . . ? C9 Ru1 Cl1 106.65(7) . . ? C1 Ru1 Cl1 84.57(6) . . ? Cl2 Ru1 Cl1 162.299(19) . . ? C9 Ru1 P1 99.26(7) . . ? C1 Ru1 P1 162.02(6) . . ? Cl2 Ru1 P1 90.413(19) . . ? Cl1 Ru1 P1 89.962(18) . . ? C41 P1 C31 102.24(10) . . ? C41 P1 C51 110.61(10) . . ? C31 P1 C51 102.74(10) . . ? C41 P1 Ru1 115.68(7) . . ? C31 P1 Ru1 110.03(7) . . ? C51 P1 Ru1 114.08(7) . . ? C1 N1 C2 110.84(18) . . ? C1 N1 C21 126.14(18) . . ? C2 N1 C21 122.86(18) . . ? C1 N2 C3 112.15(18) . . ? C1 N2 C4 121.57(19) . . ? C3 N2 C4 126.28(18) . . ? C6 O2 C7 116.22(19) . . ? N2 C1 N1 103.87(18) . . ? N2 C1 Ru1 121.29(15) . . ? N1 C1 Ru1 134.58(15) . . ? C3 C2 N1 106.9(2) . . ? C3 C2 H2 126.6 . . ? N1 C2 H2 126.6 . . ? C2 C3 N2 106.26(19) . . ? C2 C3 H3 126.9 . . ? N2 C3 H3 126.9 . . ? N2 C4 C6 110.36(18) . . ? N2 C4 C5 112.25(18) . . ? C6 C4 C5 111.94(18) . . ? N2 C4 H4 107.3 . . ? C6 C4 H4 107.3 . . ? C5 C4 H4 107.3 . . ? 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 . . ? O1 C6 O2 125.8(2) . . ? O1 C6 C4 126.0(2) . . ? O2 C6 C4 108.21(19) . . ? O2 C7 C8 106.2(2) . . ? O2 C7 H7A 110.5 . . ? C8 C7 H7A 110.5 . . ? O2 C7 H7B 110.5 . . ? C8 C7 H7B 110.5 . . ? H7A C7 H7B 108.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 Ru1 135.11(16) . . ? C10 C9 H9 112.4 . . ? Ru1 C9 H9 112.4 . . ? C15 C10 C11 117.9(2) . . ? C15 C10 C9 117.8(2) . . ? C11 C10 C9 124.25(19) . . ? C12 C11 C10 120.8(2) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 119.8(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.0(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 121.1(2) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? C26 C21 C22 122.61(19) . . ? C26 C21 N1 118.10(19) . . ? C22 C21 N1 119.24(19) . . ? C23 C22 C21 117.2(2) . . ? C23 C22 C27 121.3(2) . . ? C21 C22 C27 121.50(19) . . ? C22 C23 C24 122.2(2) . . ? C22 C23 H23 118.9 . . ? C24 C23 H23 118.9 . . ? C25 C24 C23 118.6(2) . . ? C25 C24 C28 121.0(2) . . ? C23 C24 C28 120.4(2) . . ? C24 C25 C26 121.6(2) . . ? C24 C25 H25 119.2 . . ? C26 C25 H25 119.2 . . ? C21 C26 C25 117.9(2) . . ? C21 C26 C29 120.9(2) . . ? C25 C26 C29 121.2(2) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C36 C31 C32 109.67(18) . . ? C36 C31 P1 114.64(15) . . ? C32 C31 P1 111.40(14) . . ? C36 C31 H31 106.9 . . ? C32 C31 H31 106.9 . . ? P1 C31 H31 106.9 . . ? C33 C32 C31 110.91(18) . . ? C33 C32 H32A 109.5 . . ? C31 C32 H32A 109.5 . . ? C33 C32 H32B 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 108.0 . . ? C32 C33 C34 111.53(19) . . ? C32 C33 H33A 109.3 . . ? C34 C33 H33A 109.3 . . ? C32 C33 H33B 109.3 . . ? C34 C33 H33B 109.3 . . ? H33A C33 H33B 108.0 . . ? C33 C34 C35 110.7(2) . . ? C33 C34 H34A 109.5 . . ? C35 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? C35 C34 H34B 109.5 . . ? H34A C34 H34B 108.1 . . ? C34 C35 C36 111.6(2) . . ? C34 C35 H35A 109.3 . . ? C36 C35 H35A 109.3 . . ? C34 C35 H35B 109.3 . . ? C36 C35 H35B 109.3 . . ? H35A C35 H35B 108.0 . . ? C31 C36 C35 110.13(19) . . ? C31 C36 H36A 109.6 . . ? C35 C36 H36A 109.6 . . ? C31 C36 H36B 109.6 . . ? C35 C36 H36B 109.6 . . ? H36A C36 H36B 108.1 . . ? C42 C41 C46 110.34(18) . . ? C42 C41 P1 115.05(15) . . ? C46 C41 P1 115.31(16) . . ? C42 C41 H41 105.0 . . ? C46 C41 H41 105.0 . . ? P1 C41 H41 105.0 . . ? C41 C42 C43 110.7(2) . . ? C41 C42 H42A 109.5 . . ? C43 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? C43 C42 H42B 109.5 . . ? H42A C42 H42B 108.1 . . ? C44 C43 C42 111.5(2) . . ? C44 C43 H43A 109.3 . . ? C42 C43 H43A 109.3 . . ? C44 C43 H43B 109.3 . . ? C42 C43 H43B 109.3 . . ? H43A C43 H43B 108.0 . . ? C43 C44 C45 110.9(2) . . ? C43 C44 H44A 109.5 . . ? C45 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? C45 C44 H44B 109.5 . . ? H44A C44 H44B 108.0 . . ? C44 C45 C46 111.3(2) . . ? C44 C45 H45A 109.4 . . ? C46 C45 H45A 109.4 . . ? C44 C45 H45B 109.4 . . ? C46 C45 H45B 109.4 . . ? H45A C45 H45B 108.0 . . ? C45 C46 C41 109.95(19) . . ? C45 C46 H46A 109.7 . . ? C41 C46 H46A 109.7 . . ? C45 C46 H46B 109.7 . . ? C41 C46 H46B 109.7 . . ? H46A C46 H46B 108.2 . . ? C52 C51 C56 109.60(17) . . ? C52 C51 P1 118.22(15) . . ? C56 C51 P1 112.18(14) . . ? C52 C51 H51 105.2 . . ? C56 C51 H51 105.2 . . ? P1 C51 H51 105.2 . . ? C53 C52 C51 109.72(18) . . ? C53 C52 H52A 109.7 . . ? C51 C52 H52A 109.7 . . ? C53 C52 H52B 109.7 . . ? C51 C52 H52B 109.7 . . ? H52A C52 H52B 108.2 . . ? C54 C53 C52 112.12(18) . . ? C54 C53 H53A 109.2 . . ? C52 C53 H53A 109.2 . . ? C54 C53 H53B 109.2 . . ? C52 C53 H53B 109.2 . . ? H53A C53 H53B 107.9 . . ? C53 C54 C55 110.66(18) . . ? C53 C54 H54A 109.5 . . ? C55 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? C55 C54 H54B 109.5 . . ? H54A C54 H54B 108.1 . . ? C54 C55 C56 110.59(19) . . ? C54 C55 H55A 109.5 . . ? C56 C55 H55A 109.5 . . ? C54 C55 H55B 109.5 . . ? C56 C55 H55B 109.5 . . ? H55A C55 H55B 108.1 . . ? C51 C56 C55 110.48(17) . . ? C51 C56 H56A 109.6 . . ? C55 C56 H56A 109.6 . . ? C51 C56 H56B 109.6 . . ? C55 C56 H56B 109.6 . . ? H56A C56 H56B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.341 _refine_diff_density_min -1.338 _refine_diff_density_rms 0.107