#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/47/1504709.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1504709 loop_ _publ_author_name 'Chung, Cheol K.' 'Grubbs, Robert H.' _publ_section_title ; Olefin metathesis catalyst: stabilization effect of backbone substitutions of N-heterocyclic carbene. ; _journal_issue 13 _journal_name_full 'Organic letters' _journal_page_first 2693 _journal_page_last 2696 _journal_paper_doi 10.1021/ol800824h _journal_volume 10 _journal_year 2008 _chemical_formula_moiety 'C30 H36 Cl2 N2 O Ru' _chemical_formula_sum 'C30 H36 Cl2 N2 O Ru' _chemical_formula_weight 612.58 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.1270(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.5479(3) _cell_length_b 15.7574(5) _cell_length_c 18.9019(6) _cell_measurement_reflns_used 95235 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 52.95 _cell_measurement_theta_min 2.51 _cell_volume 2821.82(15) _computing_cell_refinement 'Bruker SAINT-Plus v7.34A' _computing_data_collection 'Bruker APEX2 v2.1-0' _computing_data_reduction 'Bruker SAINT-Plus v7.34A' _computing_molecular_graphics 'Bruker XP v5.1' _computing_publication_material 'Bruker XCIF 2008' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.872 _diffrn_measurement_device_type 'Bruker KAPPA APEX II' _diffrn_measurement_method '\w scans; 18 settings' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 170605 _diffrn_reflns_theta_full 33.1 _diffrn_reflns_theta_max 53.24 _diffrn_reflns_theta_min 2.15 _exptl_absorpt_coefficient_mu 0.770 _exptl_absorpt_correction_type none _exptl_crystal_colour 'Dark green' _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 1264 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _refine_diff_density_max 1.788 _refine_diff_density_min -1.614 _refine_diff_density_rms 0.094 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.690 _refine_ls_number_parameters 332 _refine_ls_number_reflns 29561 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.690 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0308 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details w=1/s^2^(Fo^2^) _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.0520 _reflns_number_gt 21856 _reflns_number_total 29561 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ol800824h-file003.cif _cod_data_source_block 19 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_refine_ls_weighting_scheme' value 'Sigma' changed to 'sigma' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M P2(1)/c _cod_database_code 1504709 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' 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 Ru1 Ru 0.263828(4) 0.710399(3) 0.911849(3) 0.01124(1) Uani 1 1 d . Cl1 Cl 0.478493(14) 0.743877(11) 0.981887(10) 0.01881(3) Uani 1 1 d . Cl2 Cl 0.100227(16) 0.674842(10) 0.813876(9) 0.01855(3) Uani 1 1 d . O1 O 0.33200(5) 0.57315(3) 0.91973(3) 0.01981(9) Uani 1 1 d . N1 N 0.24610(5) 0.87516(3) 0.84523(3) 0.01455(9) Uani 1 1 d . N2 N 0.14081(5) 0.88464(3) 0.94044(3) 0.01401(8) Uani 1 1 d . C1 C 0.20891(5) 0.83059(4) 0.90137(3) 0.01170(9) Uani 1 1 d . C2 C 0.22216(7) 0.96837(4) 0.85099(4) 0.01680(11) Uani 1 1 d . C3 C 0.11935(7) 0.96861(4) 0.90729(4) 0.01893(11) Uani 1 1 d . H3A H 0.1426 1.0144 0.9427 0.023 Uiso 1 1 calc R H3B H 0.0207 0.9758 0.8849 0.023 Uiso 1 1 calc R C4 C 0.15746(9) 1.00658(5) 0.78072(4) 0.02500(14) Uani 1 1 d . H4A H 0.2255 1.0034 0.7460 0.038 Uiso 1 1 calc R H4B H 0.1330 1.0661 0.7881 0.038 Uiso 1 1 calc R H4C H 0.0721 0.9749 0.7627 0.038 Uiso 1 1 calc R C5 C 0.36153(8) 1.01125(5) 0.87943(5) 0.02747(15) Uani 1 1 d . H5A H 0.3993 0.9853 0.9249 0.041 Uiso 1 1 calc R H5B H 0.3453 1.0719 0.8866 0.041 Uiso 1 1 calc R H5C H 0.4293 1.0041 0.8450 0.041 Uiso 1 1 calc R C6 C 0.32781(6) 0.84130(4) 0.79328(4) 0.01497(10) Uani 1 1 d . C7 C 0.26488(6) 0.82935(4) 0.72387(4) 0.01813(11) Uani 1 1 d . H7 H 0.1676 0.8420 0.7116 0.022 Uiso 1 1 calc R C8 C 0.34336(7) 0.79902(5) 0.67220(4) 0.02046(12) Uani 1 1 d . H8 H 0.3005 0.7923 0.6244 0.025 Uiso 1 1 calc R C9 C 0.48466(7) 0.77845(5) 0.69038(4) 0.02389(14) Uani 1 1 d . H9 H 0.5380 0.7565 0.6553 0.029 Uiso 1 1 calc R C10 C 0.54760(7) 0.78996(6) 0.75957(4) 0.02741(15) Uani 1 1 d . H10 H 0.6443 0.7757 0.7718 0.033 Uiso 1 1 calc R C11 C 0.47044(7) 0.82233(5) 0.81174(4) 0.02194(13) Uani 1 1 d . H11 H 0.5145 0.8313 0.8590 0.026 Uiso 1 1 calc R C12 C 0.06329(6) 0.86023(4) 0.99717(3) 0.01244(9) Uani 1 1 d . C13 C 0.12797(6) 0.86657(4) 1.06713(3) 0.01316(9) Uani 1 1 d . C14 C 0.05614(6) 0.83501(4) 1.12157(4) 0.01493(10) Uani 1 1 d . H14 H 0.0992 0.8381 1.1696 0.018 Uiso 1 1 calc R C15 C -0.07807(6) 0.79903(4) 1.10656(4) 0.01599(10) Uani 1 1 d . C16 C -0.14281(6) 0.79851(4) 1.03656(4) 0.01649(11) Uani 1 1 d . H16 H -0.2362 0.7771 1.0266 0.020 Uiso 1 1 calc R C17 C -0.07437(6) 0.82857(4) 0.98065(4) 0.01476(10) Uani 1 1 d . C18 C 0.27370(6) 0.90417(5) 1.08389(4) 0.01923(12) Uani 1 1 d . H18A H 0.3414 0.8699 1.0612 0.029 Uiso 1 1 calc R H18B H 0.3007 0.9046 1.1356 0.029 Uiso 1 1 calc R H18C H 0.2736 0.9624 1.0657 0.029 Uiso 1 1 calc R C19 C -0.15100(8) 0.76064(5) 1.16518(4) 0.02428(14) Uani 1 1 d . H19A H -0.2170 0.8020 1.1812 0.036 Uiso 1 1 calc R H19B H -0.0805 0.7451 1.2053 0.036 Uiso 1 1 calc R H19C H -0.2029 0.7098 1.1472 0.036 Uiso 1 1 calc R C20 C -0.14394(7) 0.82156(5) 0.90502(4) 0.02248(13) Uani 1 1 d . H20A H -0.2386 0.7974 0.9047 0.034 Uiso 1 1 calc R H20B H -0.0874 0.7847 0.8779 0.034 Uiso 1 1 calc R H20C H -0.1512 0.8781 0.8832 0.034 Uiso 1 1 calc R C21 C 0.16547(6) 0.67356(4) 0.98342(4) 0.01403(9) Uani 1 1 d . H21 H 0.1036 0.7107 1.0041 0.017 Uiso 1 1 calc R C22 C 0.18411(6) 0.58686(4) 1.00759(4) 0.01627(10) Uani 1 1 d . C23 C 0.11581(7) 0.55355(4) 1.06297(4) 0.02077(12) Uani 1 1 d . H23 H 0.0558 0.5888 1.0867 0.025 Uiso 1 1 calc R C24 C 0.13537(9) 0.46920(5) 1.08344(5) 0.02801(16) Uani 1 1 d . H24 H 0.0883 0.4465 1.1206 0.034 Uiso 1 1 calc R C25 C 0.22474(9) 0.41854(5) 1.04873(5) 0.03207(18) Uani 1 1 d . H25 H 0.2384 0.3610 1.0629 0.038 Uiso 1 1 calc R C26 C 0.29447(9) 0.44955(5) 0.99404(5) 0.02895(16) Uani 1 1 d . H26 H 0.3558 0.4142 0.9712 0.035 Uiso 1 1 calc R C27 C 0.27259(7) 0.53339(4) 0.97342(4) 0.01944(12) Uani 1 1 d . C28 C 0.39175(9) 0.52190(5) 0.86588(5) 0.03065(17) Uani 1 1 d . H28 H 0.4615 0.4807 0.8903 0.037 Uiso 1 1 calc R C29 C 0.46723(9) 0.58325(7) 0.82227(6) 0.0362(2) Uani 1 1 d . H29A H 0.3983 0.6216 0.7962 0.054 Uiso 1 1 calc R H29B H 0.5167 0.5516 0.7883 0.054 Uiso 1 1 calc R H29C H 0.5356 0.6163 0.8540 0.054 Uiso 1 1 calc R C30 C 0.27534(12) 0.47345(6) 0.82092(6) 0.0420(2) Uani 1 1 d . H30A H 0.2223 0.4397 0.8521 0.063 Uiso 1 1 calc R H30B H 0.3171 0.4357 0.7880 0.063 Uiso 1 1 calc R H30C H 0.2116 0.5137 0.7936 0.063 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 0.01196(2) 0.01090(1) 0.01104(2) -0.00009(2) 0.00211(1) 0.00140(1) Cl1 0.01314(5) 0.02215(7) 0.02041(8) -0.00093(5) -0.00079(5) 0.00156(5) Cl2 0.02237(6) 0.01978(6) 0.01286(7) -0.00092(5) -0.00034(5) -0.00391(5) O1 0.0235(2) 0.01379(18) 0.0227(3) -0.00163(17) 0.00529(18) 0.00479(15) N1 0.01719(19) 0.01372(19) 0.0138(2) 0.00298(16) 0.00626(17) 0.00255(15) N2 0.01781(19) 0.01140(18) 0.0138(2) 0.00168(15) 0.00594(17) 0.00213(15) C1 0.01137(18) 0.0129(2) 0.0110(2) 0.00101(17) 0.00199(17) 0.00052(15) C2 0.0218(2) 0.0129(2) 0.0166(3) 0.00266(19) 0.0060(2) 0.00128(19) C3 0.0258(3) 0.0129(2) 0.0198(3) 0.0034(2) 0.0094(2) 0.0043(2) C4 0.0367(4) 0.0200(3) 0.0190(4) 0.0064(2) 0.0059(3) 0.0079(3) C5 0.0276(3) 0.0228(3) 0.0327(5) -0.0020(3) 0.0068(3) -0.0072(3) C6 0.0152(2) 0.0165(2) 0.0142(3) 0.00240(19) 0.00597(19) 0.00094(18) C7 0.0167(2) 0.0214(3) 0.0165(3) 0.0000(2) 0.0028(2) 0.0006(2) C8 0.0216(3) 0.0263(3) 0.0137(3) -0.0012(2) 0.0027(2) -0.0007(2) C9 0.0195(3) 0.0361(4) 0.0175(3) -0.0039(3) 0.0078(2) 0.0006(2) C10 0.0161(2) 0.0479(5) 0.0190(4) -0.0035(3) 0.0050(2) 0.0053(3) C11 0.0160(2) 0.0359(4) 0.0142(3) -0.0011(3) 0.0027(2) 0.0041(2) C12 0.01342(19) 0.0120(2) 0.0126(3) 0.00051(17) 0.00439(18) 0.00149(16) C13 0.01308(19) 0.0129(2) 0.0139(3) -0.00075(18) 0.00307(18) -0.00023(16) C14 0.0166(2) 0.0162(2) 0.0122(3) -0.00009(19) 0.00271(19) -0.00124(18) C15 0.0166(2) 0.0157(2) 0.0169(3) -0.00061(19) 0.0066(2) -0.00182(18) C16 0.0129(2) 0.0180(3) 0.0190(3) -0.0024(2) 0.00387(19) -0.00113(17) C17 0.0134(2) 0.0158(2) 0.0150(3) -0.00163(19) 0.00138(19) 0.00171(17) C18 0.0159(2) 0.0232(3) 0.0185(3) -0.0010(2) 0.0018(2) -0.0054(2) C19 0.0262(3) 0.0259(3) 0.0224(4) 0.0016(3) 0.0098(3) -0.0083(2) C20 0.0201(3) 0.0288(3) 0.0174(3) -0.0017(3) -0.0023(2) 0.0001(2) C21 0.0157(2) 0.0127(2) 0.0135(3) 0.00093(18) 0.00120(19) 0.00066(17) C22 0.0200(2) 0.0127(2) 0.0150(3) 0.00177(19) -0.0023(2) -0.00167(18) C23 0.0272(3) 0.0189(3) 0.0150(3) 0.0035(2) -0.0022(2) -0.0065(2) C24 0.0405(4) 0.0215(3) 0.0193(4) 0.0080(3) -0.0075(3) -0.0124(3) C25 0.0463(4) 0.0143(3) 0.0315(5) 0.0075(3) -0.0112(3) -0.0036(3) C26 0.0377(4) 0.0130(3) 0.0339(5) 0.0019(3) -0.0043(3) 0.0048(2) C27 0.0237(3) 0.0125(2) 0.0209(3) 0.0012(2) -0.0017(2) 0.00193(19) C28 0.0381(4) 0.0242(3) 0.0306(5) -0.0066(3) 0.0083(3) 0.0140(3) C29 0.0334(4) 0.0453(5) 0.0323(5) -0.0057(4) 0.0138(3) 0.0122(4) C30 0.0647(6) 0.0226(4) 0.0381(6) -0.0134(4) 0.0038(5) 0.0026(4) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C21 Ru1 C1 102.96(2) yes C21 Ru1 O1 79.51(2) yes C1 Ru1 O1 177.51(2) yes C21 Ru1 Cl2 98.94(2) yes C1 Ru1 Cl2 90.426(18) yes O1 Ru1 Cl2 88.943(15) yes C21 Ru1 Cl1 98.37(2) yes C1 Ru1 Cl1 92.486(17) yes O1 Ru1 Cl1 87.354(14) yes Cl2 Ru1 Cl1 161.314(6) yes C27 O1 C28 119.52(6) ? C27 O1 Ru1 110.09(4) ? C28 O1 Ru1 127.91(5) ? C1 N1 C6 124.19(5) ? C1 N1 C2 113.28(5) ? C6 N1 C2 121.23(5) ? C1 N2 C12 124.86(5) ? C1 N2 C3 112.79(5) ? C12 N2 C3 120.35(5) ? N2 C1 N1 107.03(5) ? N2 C1 Ru1 133.96(4) ? N1 C1 Ru1 118.99(4) ? N1 C2 C4 112.08(6) ? N1 C2 C5 109.03(5) ? C4 C2 C5 111.97(6) ? N1 C2 C3 99.78(5) ? C4 C2 C3 112.32(6) ? C5 C2 C3 111.02(6) ? N2 C3 C2 103.09(5) ? C7 C6 C11 120.16(6) ? C7 C6 N1 119.39(5) ? C11 C6 N1 120.42(6) ? C6 C7 C8 120.29(6) ? C7 C8 C9 119.94(7) ? C10 C9 C8 119.92(6) ? C9 C10 C11 120.66(6) ? C6 C11 C10 119.00(7) ? C13 C12 C17 121.97(5) ? C13 C12 N2 118.91(5) ? C17 C12 N2 119.10(6) ? C12 C13 C14 118.28(5) ? C12 C13 C18 121.09(5) ? C14 C13 C18 120.61(6) ? C13 C14 C15 121.09(6) ? C16 C15 C14 118.96(6) ? C16 C15 C19 120.43(6) ? C14 C15 C19 120.61(6) ? C15 C16 C17 121.70(5) ? C16 C17 C12 117.80(6) ? C16 C17 C20 120.19(6) ? C12 C17 C20 121.89(6) ? C22 C21 Ru1 118.58(5) ? C23 C22 C27 118.71(6) ? C23 C22 C21 122.67(6) ? C27 C22 C21 118.62(6) ? C24 C23 C22 120.45(7) ? C23 C24 C25 119.10(8) ? C26 C25 C24 121.94(7) ? C27 C26 C25 118.43(8) ? O1 C27 C26 125.51(7) ? O1 C27 C22 113.14(5) ? C26 C27 C22 121.36(7) ? O1 C28 C29 106.20(7) ? O1 C28 C30 110.12(7) ? C29 C28 C30 112.46(9) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Ru1 C21 1.8342(6) yes Ru1 C1 1.9686(6) yes Ru1 O1 2.2581(5) yes Ru1 Cl2 2.33786(17) yes Ru1 Cl1 2.35763(17) yes O1 C27 1.3736(9) ? O1 C28 1.4690(9) ? N1 C1 1.3560(8) ? N1 C6 1.4310(8) ? N1 C2 1.4925(8) ? N2 C1 1.3464(8) ? N2 C12 1.4292(8) ? N2 C3 1.4674(8) ? C2 C4 1.5181(10) ? C2 C5 1.5294(10) ? C2 C3 1.5348(9) ? C6 C7 1.3864(10) ? C6 C11 1.3957(9) ? C7 C8 1.3876(10) ? C8 C9 1.3886(10) ? C9 C10 1.3817(11) ? C10 C11 1.3985(10) ? C12 C13 1.3919(9) ? C12 C17 1.4043(8) ? C13 C14 1.3970(9) ? C13 C18 1.5093(8) ? C14 C15 1.3978(8) ? C15 C16 1.3891(10) ? C15 C19 1.5067(10) ? C16 C17 1.3927(9) ? C17 C20 1.5038(10) ? C21 C22 1.4445(8) ? C22 C23 1.4021(10) ? C22 C27 1.4057(10) ? C23 C24 1.3904(10) ? C24 C25 1.3910(14) ? C25 C26 1.3862(14) ? C26 C27 1.3859(10) ? C28 C29 1.5102(14) ? C28 C30 1.5186(14) ?