# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Young Keun Chung' _publ_contact_author_email YKCHUNG@SNU.AC.KR _publ_section_title ; Cobalt/Rhodium Heterobimetallic Nanoparticle-Catalyzed Carbonylative [2+2+1] Cycloaddition of Allenes and Bisallenes to Pauson-Khand-Type Reaction Products ; loop_ _publ_author_name 'Young Keun Chung.' 'Soo Young Choi.' 'Eunha Kim.' 'Hyeong-Mook Kim.' ; Ji Hoon Park ; # Attachment '1c.cif' data_1c _database_code_depnum_ccdc_archive 'CCDC 650888' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 O' _chemical_formula_sum 'C19 H16 O' _chemical_formula_weight 260.32 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' 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 'P 21/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 11.6112(5) _cell_length_b 6.3622(3) _cell_length_c 19.4174(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.098(2) _cell_angle_gamma 90.00 _cell_volume 1434.15(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7556 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9576 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_process_details 'R. H. Blessing, Acta. Crystallogr., Sect A, 1995, 51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5891 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.40 _reflns_number_total 3231 _reflns_number_gt 2308 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP32 _computing_publication_material WinGX _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^)+(0.0456P)^2^+0.1872P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3231 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.33038(10) 0.00807(15) -0.02987(6) 0.0769(3) Uani 1 1 d . . . C1 C 0.33034(12) 0.1827(2) -0.00311(7) 0.0535(3) Uani 1 1 d . . . C2 C 0.24613(11) 0.35381(19) -0.01848(6) 0.0469(3) Uani 1 1 d . . . C3 C 0.16591(12) 0.3312(2) -0.06836(7) 0.0531(3) Uani 1 1 d . . . H3 H 0.1693(11) 0.194(2) -0.0915(7) 0.059(4) Uiso 1 1 d . . . C4 C 0.07895(11) 0.4771(2) -0.09486(6) 0.0559(3) Uani 1 1 d . . . C5 C 0.01368(14) 0.4163(3) -0.15270(8) 0.0759(5) Uani 1 1 d . . . H5 H 0.0257 0.2849 -0.1722 0.091 Uiso 1 1 calc R . . C6 C -0.06823(17) 0.5484(4) -0.18119(10) 0.0987(7) Uani 1 1 d . . . H6 H -0.1107 0.5058 -0.2198 0.118 Uiso 1 1 calc R . . C7 C -0.08738(16) 0.7422(4) -0.15297(11) 0.0991(7) Uani 1 1 d . . . H7 H -0.1425 0.8311 -0.1726 0.119 Uiso 1 1 calc R . . C8 C -0.02512(14) 0.8053(3) -0.09565(9) 0.0830(5) Uani 1 1 d . . . H8 H -0.0385 0.9366 -0.0764 0.100 Uiso 1 1 calc R . . C9 C 0.05749(12) 0.6737(2) -0.06660(8) 0.0652(4) Uani 1 1 d . . . H9 H 0.0991 0.7173 -0.0278 0.078 Uiso 1 1 calc R . . C10 C 0.27773(11) 0.53557(19) 0.02726(6) 0.0496(3) Uani 1 1 d . . . H10A H 0.2172 0.5646 0.0597 0.059 Uiso 1 1 calc R . . H10B H 0.2921 0.6611 0.0004 0.059 Uiso 1 1 calc R . . C11 C 0.38578(11) 0.4626(2) 0.06404(6) 0.0478(3) Uani 1 1 d . . . C12 C 0.45065(11) 0.6054(2) 0.11209(7) 0.0584(4) Uani 1 1 d . . . H12A H 0.4599 0.7411 0.0901 0.070 Uiso 1 1 calc R . . H12B H 0.5269 0.5477 0.1207 0.070 Uiso 1 1 calc R . . C13 C 0.39169(10) 0.6364(2) 0.18026(6) 0.0488(3) Uani 1 1 d . . . C14 C 0.33684(13) 0.8220(2) 0.19604(7) 0.0640(4) Uani 1 1 d . . . H14 H 0.3327 0.9291 0.1635 0.077 Uiso 1 1 calc R . . C15 C 0.28792(14) 0.8505(3) 0.25983(8) 0.0746(5) Uani 1 1 d . . . H15 H 0.2512 0.9766 0.2698 0.090 Uiso 1 1 calc R . . C16 C 0.29317(13) 0.6948(3) 0.30821(7) 0.0717(4) Uani 1 1 d . . . H16 H 0.2607 0.7148 0.3511 0.086 Uiso 1 1 calc R . . C17 C 0.34670(13) 0.5087(3) 0.29298(7) 0.0677(4) Uani 1 1 d . . . H17 H 0.3503 0.4019 0.3257 0.081 Uiso 1 1 calc R . . C18 C 0.39512(12) 0.4793(2) 0.22952(7) 0.0581(4) Uani 1 1 d . . . H18 H 0.4306 0.3521 0.2196 0.070 Uiso 1 1 calc R . . C19 C 0.41282(12) 0.2656(2) 0.04726(7) 0.0544(3) Uani 1 1 d . . . H19 H 0.4797(13) 0.189(2) 0.0638(7) 0.073(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0944(8) 0.0452(6) 0.0911(8) -0.0090(5) -0.0014(6) 0.0058(5) C1 0.0651(8) 0.0419(7) 0.0537(7) 0.0042(6) 0.0096(6) 0.0015(6) C2 0.0530(7) 0.0447(7) 0.0431(6) 0.0036(5) 0.0059(5) -0.0017(6) C3 0.0576(8) 0.0531(8) 0.0486(7) -0.0025(6) 0.0050(6) -0.0051(7) C4 0.0499(7) 0.0695(9) 0.0483(7) 0.0085(6) 0.0028(6) -0.0076(7) C5 0.0683(10) 0.0990(12) 0.0602(9) 0.0067(9) -0.0069(7) -0.0172(9) C6 0.0735(12) 0.146(2) 0.0759(11) 0.0265(13) -0.0241(9) -0.0150(13) C7 0.0641(11) 0.1316(18) 0.1010(14) 0.0478(14) -0.0104(10) 0.0119(12) C8 0.0674(10) 0.0913(13) 0.0906(12) 0.0259(10) 0.0072(9) 0.0137(9) C9 0.0577(8) 0.0741(10) 0.0637(8) 0.0106(7) -0.0013(6) 0.0065(8) C10 0.0564(7) 0.0455(7) 0.0468(6) 0.0014(5) 0.0017(5) 0.0030(6) C11 0.0502(7) 0.0530(7) 0.0404(6) 0.0048(5) 0.0069(5) -0.0004(6) C12 0.0525(8) 0.0699(9) 0.0528(7) -0.0035(7) 0.0012(6) -0.0055(7) C13 0.0434(6) 0.0582(8) 0.0445(6) -0.0026(6) -0.0067(5) -0.0010(6) C14 0.0697(9) 0.0624(9) 0.0598(8) 0.0062(7) -0.0024(7) 0.0105(8) C15 0.0755(10) 0.0771(11) 0.0715(10) -0.0067(8) 0.0046(8) 0.0245(9) C16 0.0642(9) 0.1013(13) 0.0497(8) -0.0063(8) 0.0044(6) 0.0104(9) C17 0.0701(9) 0.0839(11) 0.0488(7) 0.0122(7) -0.0033(7) 0.0094(8) C18 0.0591(8) 0.0605(8) 0.0545(7) 0.0007(6) -0.0045(6) 0.0105(7) C19 0.0555(8) 0.0536(8) 0.0541(7) 0.0078(6) 0.0026(6) 0.0089(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 C10 C2 1.4994(17) . ? C10 C11 1.5049(18) . ? C11 C19 1.3343(19) . ? C11 C12 1.4953(18) . ? C19 C1 1.4546(19) . ? C2 C3 1.3386(18) . ? C2 C1 1.4897(18) . ? C13 C14 1.3788(19) . ? C13 C18 1.3835(18) . ? C13 C12 1.5148(18) . ? C4 C9 1.390(2) . ? C4 C5 1.397(2) . ? C4 C3 1.4582(19) . ? O1 C1 1.2265(15) . ? C18 C17 1.377(2) . ? C9 C8 1.385(2) . ? C14 C15 1.385(2) . ? C17 C16 1.372(2) . ? C16 C15 1.366(2) . ? C5 C6 1.377(3) . ? C8 C7 1.375(3) . ? C6 C7 1.369(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 C2 C10 C11 103.63(10) . . ? C19 C11 C12 127.23(12) . . ? C19 C11 C10 111.82(12) . . ? C12 C11 C10 120.94(12) . . ? C11 C19 C1 110.48(12) . . ? C3 C2 C1 120.74(12) . . ? C3 C2 C10 132.12(12) . . ? C1 C2 C10 107.02(10) . . ? C14 C13 C18 118.19(12) . . ? C14 C13 C12 121.60(12) . . ? C18 C13 C12 120.18(12) . . ? C9 C4 C5 117.87(14) . . ? C9 C4 C3 124.18(12) . . ? C5 C4 C3 117.95(14) . . ? O1 C1 C19 127.43(13) . . ? O1 C1 C2 125.64(13) . . ? C19 C1 C2 106.91(11) . . ? C2 C3 C4 130.86(13) . . ? C11 C12 C13 113.18(10) . . ? C17 C18 C13 120.92(13) . . ? C8 C9 C4 120.74(15) . . ? C13 C14 C15 120.68(13) . . ? C16 C17 C18 120.30(14) . . ? C15 C16 C17 119.48(13) . . ? C6 C5 C4 120.92(18) . . ? C16 C15 C14 120.43(14) . . ? C7 C8 C9 120.15(19) . . ? C7 C6 C5 120.32(18) . . ? C6 C7 C8 119.99(18) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.134 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.026 # Attachment '1b.cif' data_1b _database_code_depnum_ccdc_archive 'CCDC 650889' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 O' _chemical_formula_sum 'C19 H16 O' _chemical_formula_weight 260.32 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' 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 'C c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 27.151(3) _cell_length_b 7.5779(4) _cell_length_c 7.2416(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.694(3) _cell_angle_gamma 90.00 _cell_volume 1459.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1297 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2833 _diffrn_reflns_av_R_equivalents 0.0130 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.40 _reflns_number_total 2830 _reflns_number_gt 1980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP32 _computing_publication_material WinGX _refine_special_details ; We first solved the crystal using the space C2/c. However, the result obtained was not consistent with that of NMR study. If we solved the crystal structure using disorder, we had problems to assign the positions of double bonds. Thus, we solved the crystal structure using the space group Cc. The result obtained was well consistent with that of NMR study. That is why we solved the crystal structure using the space group Cc. 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^)+(0.0591P)^2^+0.4603P] 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 SHELXL _refine_ls_extinction_coef 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(4) _refine_ls_number_reflns 2830 _refine_ls_number_parameters 182 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.3342(2) 0.14737(18) 0.4275(9) 0.1131(8) Uani 1 1 d . . . C1 C 0.22393(14) 0.7529(5) 0.4472(5) 0.0491(10) Uani 1 1 d . . . C2 C 0.20836(17) 0.8676(6) 0.5718(6) 0.0749(14) Uani 1 1 d . . . H2 H 0.2317 0.9414 0.6460 0.090 Uiso 1 1 calc R . . C3 C 0.1592(2) 0.8740(9) 0.5875(7) 0.0989(18) Uani 1 1 d . . . H3 H 0.1494 0.9532 0.6713 0.119 Uiso 1 1 calc R . . C4 C 0.12376(19) 0.7647(7) 0.4809(6) 0.0827(17) Uani 1 1 d . . . H4 H 0.0905 0.7679 0.4953 0.099 Uiso 1 1 calc R . . C5 C 0.13751(17) 0.6555(7) 0.3584(8) 0.0834(16) Uani 1 1 d . . . H5 H 0.1138 0.5826 0.2848 0.100 Uiso 1 1 calc R . . C6 C 0.18912(17) 0.6492(6) 0.3386(7) 0.0757(14) Uani 1 1 d . . . H6 H 0.1986 0.5736 0.2508 0.091 Uiso 1 1 calc R . . C7 C 0.27809(15) 0.7518(5) 0.4358(5) 0.0541(10) Uani 1 1 d . . . H7 H 0.2943 0.8595 0.4323 0.065 Uiso 1 1 calc R . . C8 C 0.30578(13) 0.5981(4) 0.4301(4) 0.0390(8) Uani 1 1 d . . . C9 C 0.28966(16) 0.4148(4) 0.4280(5) 0.0530(10) Uani 1 1 d . . . H9A H 0.2758 0.3895 0.5385 0.080 Uiso 1 1 calc R . . H9B H 0.2640 0.3915 0.3165 0.080 Uiso 1 1 calc R . . C10 C 0.3330(2) 0.3074(2) 0.4276(8) 0.0621(6) Uani 1 1 d . . . C11 C 0.37719(15) 0.4273(5) 0.4294(5) 0.0547(10) Uani 1 1 d . . . H11 H 0.4100 0.3922 0.4299 0.066 Uiso 1 1 calc R . . C12 C 0.36008(13) 0.6004(4) 0.4301(4) 0.0409(8) Uani 1 1 d . . . C13 C 0.38850(16) 0.7591(5) 0.4325(5) 0.0551(10) Uani 1 1 d . . . H13A H 0.3862 0.8215 0.5474 0.083 Uiso 1 1 calc R . . H13B H 0.3714 0.8312 0.3283 0.083 Uiso 1 1 calc R . . C14 C 0.44265(14) 0.7549(4) 0.4215(5) 0.0467(9) Uani 1 1 d . . . C15 C 0.45919(16) 0.8535(6) 0.2886(6) 0.0703(13) Uani 1 1 d . . . H15 H 0.4364 0.9239 0.2076 0.084 Uiso 1 1 calc R . . C16 C 0.5097(2) 0.8517(7) 0.2710(8) 0.0876(15) Uani 1 1 d . . . H16 H 0.5200 0.9180 0.1776 0.105 Uiso 1 1 calc R . . C17 C 0.54290(18) 0.7540(7) 0.3895(7) 0.0821(16) Uani 1 1 d . . . H17 H 0.5765 0.7531 0.3798 0.098 Uiso 1 1 calc R . . C18 C 0.52708(17) 0.6533(6) 0.5275(6) 0.0709(13) Uani 1 1 d . . . H18 H 0.5502 0.5856 0.6105 0.085 Uiso 1 1 calc R . . C19 C 0.47907(16) 0.6541(6) 0.5403(6) 0.0678(12) Uani 1 1 d . . . H19 H 0.4692 0.5846 0.6322 0.081 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 0.1297(16) 0.0298(8) 0.157(2) -0.004(2) -0.0257(13) -0.003(2) C1 0.040(2) 0.046(2) 0.058(2) 0.0036(16) 0.0020(17) 0.0016(16) C2 0.056(3) 0.096(3) 0.068(3) -0.033(2) 0.003(2) 0.017(2) C3 0.062(3) 0.153(5) 0.082(3) -0.037(3) 0.016(3) 0.028(3) C4 0.051(3) 0.111(4) 0.094(4) 0.011(3) 0.033(3) 0.027(2) C5 0.042(3) 0.082(3) 0.123(4) 0.001(3) 0.008(3) -0.010(2) C6 0.050(3) 0.071(3) 0.108(4) -0.024(2) 0.020(3) 0.003(2) C7 0.037(2) 0.048(2) 0.079(3) -0.0078(17) 0.0170(19) -0.0013(15) C8 0.0437(19) 0.0353(19) 0.0370(18) -0.0011(12) 0.0059(15) -0.0018(14) C9 0.064(3) 0.0428(19) 0.052(2) 0.0056(14) 0.0106(19) -0.0150(17) C10 0.0723(14) 0.0341(10) 0.0707(14) 0.008(2) -0.0069(11) 0.000(3) C11 0.0372(19) 0.052(2) 0.075(3) -0.0146(17) 0.0128(19) -0.0032(16) C12 0.045(2) 0.0358(18) 0.045(2) -0.0003(13) 0.0149(17) 0.0018(15) C13 0.051(3) 0.049(2) 0.065(3) 0.0076(17) 0.010(2) -0.0033(16) C14 0.046(2) 0.035(2) 0.063(2) -0.0002(16) 0.0203(19) -0.0019(15) C15 0.048(2) 0.066(3) 0.097(3) 0.021(2) 0.015(2) -0.003(2) C16 0.063(3) 0.102(3) 0.104(4) 0.022(3) 0.032(3) -0.012(3) C17 0.043(3) 0.103(4) 0.102(4) -0.013(3) 0.019(3) 0.006(2) C18 0.051(3) 0.067(3) 0.094(3) 0.012(2) 0.012(2) 0.002(2) C19 0.048(3) 0.072(3) 0.081(3) 0.023(2) 0.006(2) 0.002(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 O1 C10 1.213(2) . ? C1 C6 1.352(6) . ? C1 C2 1.379(5) . ? C1 C7 1.489(5) . ? C2 C3 1.363(7) . ? C3 C4 1.381(8) . ? C4 C5 1.321(6) . ? C5 C6 1.438(6) . ? C7 C8 1.392(5) . ? C8 C9 1.455(4) . ? C8 C12 1.474(2) . ? C9 C10 1.431(7) . ? C10 C11 1.503(6) . ? C11 C12 1.392(5) . ? C12 C13 1.427(5) . ? C13 C14 1.489(5) . ? C14 C15 1.365(5) . ? C14 C19 1.399(6) . ? C15 C16 1.403(7) . ? C16 C17 1.335(7) . ? C17 C18 1.393(7) . ? C18 C19 1.325(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.4(4) . . ? C6 C1 C7 123.1(4) . . ? C2 C1 C7 118.5(4) . . ? C3 C2 C1 120.8(5) . . ? C2 C3 C4 121.0(5) . . ? C5 C4 C3 119.4(5) . . ? C4 C5 C6 120.1(5) . . ? C1 C6 C5 120.2(5) . . ? C8 C7 C1 123.5(3) . . ? C7 C8 C9 129.5(3) . . ? C7 C8 C12 122.4(3) . . ? C9 C8 C12 108.1(3) . . ? C10 C9 C8 107.3(3) . . ? O1 C10 C9 126.1(6) . . ? O1 C10 C11 125.7(6) . . ? C9 C10 C11 108.16(16) . . ? C12 C11 C10 107.6(3) . . ? C11 C12 C13 127.9(3) . . ? C11 C12 C8 108.9(3) . . ? C13 C12 C8 123.3(3) . . ? C12 C13 C14 121.3(3) . . ? C15 C14 C19 116.1(4) . . ? C15 C14 C13 119.7(4) . . ? C19 C14 C13 124.2(3) . . ? C14 C15 C16 121.7(4) . . ? C17 C16 C15 119.5(5) . . ? C16 C17 C18 119.9(5) . . ? C19 C18 C17 119.9(4) . . ? C18 C19 C14 122.8(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.191 _refine_diff_density_min -0.121 _refine_diff_density_rms 0.029