# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_test #TrackingRef '18737_web_deposit_cif_file_0_ZhenghuXu_1363854580.carbonylation.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 O6' _chemical_formula_weight 456.47 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0618(12) _cell_length_b 11.3801(15) _cell_length_c 12.3091(16) _cell_angle_alpha 73.216(2) _cell_angle_beta 85.2965(19) _cell_angle_gamma 67.465(2) _cell_volume 1121.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9813 _exptl_absorpt_correction_T_max 0.9906 _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 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 5615 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3909 _reflns_number_gt 2990 _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^)+(0.0419P)^2^+0.3109P] 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 3909 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.40752(13) 0.85567(12) 0.07063(9) 0.0283(3) Uani 1 1 d . . . O2 O 0.59411(13) 0.90554(12) -0.19517(9) 0.0310(3) Uani 1 1 d . . . O4 O 0.38835(13) 0.80400(12) 0.26312(10) 0.0313(3) Uani 1 1 d . . . O3 O 0.33574(14) 0.94217(13) -0.15533(10) 0.0360(3) Uani 1 1 d . . . O5 O 0.90087(14) 0.63345(13) 0.24326(10) 0.0374(3) Uani 1 1 d . . . O6 O 0.70516(16) 0.68345(16) 0.36563(11) 0.0511(4) Uani 1 1 d . . . C5 C 0.6748(2) 0.78804(17) 0.04979(14) 0.0254(4) Uani 1 1 d . . . C7 C 0.4786(2) 0.80506(17) 0.17406(14) 0.0276(4) Uani 1 1 d . . . C3 C 0.4742(2) 0.90219(17) -0.12505(14) 0.0268(4) Uani 1 1 d . . . C15 C 0.7482(2) 0.69080(18) 0.26975(15) 0.0310(4) Uani 1 1 d . . . C23 C 0.83237(19) 0.76770(17) -0.00325(14) 0.0248(4) Uani 1 1 d . . . C28 C 0.8924(2) 0.68108(19) -0.06966(15) 0.0329(4) Uani 1 1 d . . . H28 H 0.8356 0.6316 -0.0790 0.039 Uiso 1 1 calc R . . C9 C 0.1398(2) 0.84614(17) 0.35687(14) 0.0274(4) Uani 1 1 d . . . C6 C 0.6416(2) 0.75996(17) 0.16907(14) 0.0264(4) Uani 1 1 d . . . C4 C 0.53053(19) 0.84567(17) -0.00651(14) 0.0262(4) Uani 1 1 d . . . C17 C 1.1814(2) 0.53714(17) 0.29468(15) 0.0314(4) Uani 1 1 d . . . C2 C 0.5530(2) 0.95055(19) -0.31599(14) 0.0313(4) Uani 1 1 d . . . H2A H 0.6345 0.9789 -0.3581 0.038 Uiso 1 1 calc R . . H2B H 0.4522 1.0260 -0.3308 0.038 Uiso 1 1 calc R . . C24 C 0.9194(2) 0.84029(18) 0.01075(15) 0.0294(4) Uani 1 1 d . . . H24 H 0.8814 0.8973 0.0565 0.035 Uiso 1 1 calc R . . C8 C 0.2168(2) 0.8607(2) 0.24374(15) 0.0326(4) Uani 1 1 d . . . H8A H 0.1858 0.8150 0.1998 0.039 Uiso 1 1 calc R . . H8B H 0.1828 0.9536 0.2017 0.039 Uiso 1 1 calc R . . C27 C 1.0366(2) 0.6678(2) -0.12219(16) 0.0385(5) Uani 1 1 d . . . H27 H 1.0770 0.6086 -0.1658 0.046 Uiso 1 1 calc R . . C12 C -0.0160(2) 0.8236(2) 0.56114(17) 0.0446(5) Uani 1 1 d . . . H12 H -0.0681 0.8160 0.6296 0.053 Uiso 1 1 calc R . . C26 C 1.1205(2) 0.7422(2) -0.11007(16) 0.0372(5) Uani 1 1 d . . . H26 H 1.2162 0.7346 -0.1469 0.045 Uiso 1 1 calc R . . C25 C 1.0625(2) 0.82755(19) -0.04341(16) 0.0342(4) Uani 1 1 d . . . H25 H 1.1196 0.8770 -0.0347 0.041 Uiso 1 1 calc R . . C10 C 0.2250(2) 0.7968(2) 0.45865(16) 0.0360(5) Uani 1 1 d . . . H10 H 0.3356 0.7708 0.4590 0.043 Uiso 1 1 calc R . . C14 C -0.0245(2) 0.8846(2) 0.35839(17) 0.0419(5) Uani 1 1 d . . . H14 H -0.0835 0.9187 0.2903 0.050 Uiso 1 1 calc R . . C11 C 0.1468(2) 0.7859(2) 0.56008(16) 0.0426(5) Uani 1 1 d . . . H11 H 0.2053 0.7527 0.6283 0.051 Uiso 1 1 calc R . . C1 C 0.5395(3) 0.8426(2) -0.35558(17) 0.0465(5) Uani 1 1 d . . . H1A H 0.5218 0.8718 -0.4365 0.070 Uiso 1 1 calc R . . H1B H 0.4514 0.8209 -0.3198 0.070 Uiso 1 1 calc R . . H1C H 0.6365 0.7655 -0.3359 0.070 Uiso 1 1 calc R . . C13 C -0.1019(2) 0.8728(2) 0.45978(17) 0.0499(6) Uani 1 1 d . . . H13 H -0.2124 0.8982 0.4598 0.060 Uiso 1 1 calc R . . C22 C 1.2158(2) 0.54773(18) 0.18142(16) 0.0357(5) Uani 1 1 d . . . H22 H 1.1348 0.5684 0.1292 0.043 Uiso 1 1 calc R . . C18 C 1.3038(2) 0.50549(19) 0.37138(17) 0.0386(5) Uani 1 1 d . . . H18 H 1.2822 0.4974 0.4478 0.046 Uiso 1 1 calc R . . C16 C 1.0154(2) 0.5596(2) 0.33782(16) 0.0385(5) Uani 1 1 d . . . H16A H 1.0056 0.4752 0.3740 0.046 Uiso 1 1 calc R . . H16B H 0.9945 0.6088 0.3936 0.046 Uiso 1 1 calc R . . C20 C 1.4908(2) 0.4967(2) 0.22191(19) 0.0438(5) Uani 1 1 d . . . H20 H 1.5944 0.4833 0.1975 0.053 Uiso 1 1 calc R . . C21 C 1.3699(2) 0.5277(2) 0.14565(18) 0.0441(5) Uani 1 1 d . . . H21 H 1.3920 0.5352 0.0694 0.053 Uiso 1 1 calc R . . C19 C 1.4575(2) 0.4858(2) 0.33509(19) 0.0452(5) Uani 1 1 d . . . H19 H 1.5388 0.4651 0.3870 0.054 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 0.0239(6) 0.0351(7) 0.0258(7) -0.0071(5) 0.0036(5) -0.0127(5) O2 0.0238(6) 0.0437(8) 0.0235(6) -0.0053(6) 0.0020(5) -0.0138(6) O4 0.0237(6) 0.0390(7) 0.0272(7) -0.0055(6) 0.0053(5) -0.0112(6) O3 0.0230(7) 0.0517(9) 0.0316(7) -0.0085(6) 0.0004(5) -0.0144(6) O5 0.0281(7) 0.0475(8) 0.0242(7) -0.0053(6) -0.0020(5) -0.0038(6) O6 0.0364(8) 0.0782(11) 0.0243(8) -0.0063(7) 0.0039(6) -0.0127(8) C5 0.0262(9) 0.0267(9) 0.0256(9) -0.0083(7) 0.0026(7) -0.0119(7) C7 0.0306(10) 0.0302(10) 0.0232(9) -0.0058(8) 0.0040(7) -0.0146(8) C3 0.0231(10) 0.0297(10) 0.0293(10) -0.0083(8) 0.0043(7) -0.0122(8) C15 0.0279(10) 0.0365(11) 0.0274(10) -0.0060(8) 0.0040(8) -0.0136(8) C23 0.0213(9) 0.0278(9) 0.0213(9) -0.0035(7) -0.0009(7) -0.0071(7) C28 0.0322(10) 0.0365(11) 0.0337(10) -0.0140(9) 0.0020(8) -0.0141(9) C9 0.0273(9) 0.0285(10) 0.0270(9) -0.0092(8) 0.0043(7) -0.0109(8) C6 0.0246(9) 0.0289(10) 0.0266(9) -0.0073(8) 0.0041(7) -0.0119(8) C4 0.0226(9) 0.0328(10) 0.0249(9) -0.0084(8) 0.0060(7) -0.0129(8) C17 0.0320(10) 0.0247(9) 0.0306(10) -0.0045(8) -0.0025(8) -0.0050(8) C2 0.0323(10) 0.0378(11) 0.0214(9) -0.0039(8) 0.0038(7) -0.0145(8) C24 0.0278(10) 0.0298(10) 0.0297(10) -0.0079(8) 0.0015(8) -0.0102(8) C8 0.0237(9) 0.0423(11) 0.0302(10) -0.0083(8) 0.0023(7) -0.0122(8) C27 0.0336(11) 0.0460(12) 0.0335(11) -0.0191(9) 0.0070(8) -0.0078(9) C12 0.0372(12) 0.0570(14) 0.0311(11) -0.0112(10) 0.0123(9) -0.0118(10) C26 0.0252(10) 0.0474(12) 0.0311(10) -0.0065(9) 0.0060(8) -0.0096(9) C25 0.0264(10) 0.0360(11) 0.0396(11) -0.0058(9) 0.0010(8) -0.0146(8) C10 0.0258(10) 0.0464(12) 0.0333(11) -0.0099(9) 0.0025(8) -0.0120(9) C14 0.0287(11) 0.0591(14) 0.0320(11) -0.0114(10) -0.0001(8) -0.0109(10) C11 0.0353(11) 0.0584(14) 0.0262(10) -0.0085(10) 0.0011(8) -0.0117(10) C1 0.0611(14) 0.0512(13) 0.0345(11) -0.0132(10) 0.0051(10) -0.0286(12) C13 0.0243(10) 0.0756(16) 0.0401(12) -0.0156(11) 0.0075(9) -0.0103(11) C22 0.0344(11) 0.0349(11) 0.0322(11) -0.0092(9) -0.0020(8) -0.0064(9) C18 0.0405(12) 0.0354(11) 0.0349(11) -0.0080(9) -0.0042(9) -0.0090(9) C16 0.0340(11) 0.0428(12) 0.0268(10) -0.0002(9) -0.0052(8) -0.0076(9) C20 0.0302(11) 0.0366(12) 0.0592(14) -0.0128(10) 0.0052(10) -0.0080(9) C21 0.0397(12) 0.0421(12) 0.0419(12) -0.0135(10) 0.0074(10) -0.0063(10) C19 0.0361(12) 0.0378(12) 0.0563(14) -0.0103(10) -0.0126(10) -0.0075(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.339(2) . ? O1 C4 1.3960(19) . ? O2 C3 1.3364(19) . ? O2 C2 1.455(2) . ? O4 C7 1.313(2) . ? O4 C8 1.447(2) . ? O3 C3 1.209(2) . ? O5 C15 1.343(2) . ? O5 C16 1.450(2) . ? O6 C15 1.202(2) . ? C5 C4 1.360(2) . ? C5 C6 1.442(2) . ? C5 C23 1.483(2) . ? C7 C6 1.368(2) . ? C3 C4 1.460(2) . ? C15 C6 1.463(2) . ? C23 C28 1.385(2) . ? C23 C24 1.392(2) . ? C28 C27 1.384(3) . ? C28 H28 0.9300 . ? C9 C10 1.379(2) . ? C9 C14 1.382(2) . ? C9 C8 1.500(2) . ? C17 C22 1.384(3) . ? C17 C18 1.385(3) . ? C17 C16 1.504(3) . ? C2 C1 1.494(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C24 C25 1.384(2) . ? C24 H24 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C27 C26 1.379(3) . ? C27 H27 0.9300 . ? C12 C11 1.370(3) . ? C12 C13 1.377(3) . ? C12 H12 0.9300 . ? C26 C25 1.375(3) . ? C26 H26 0.9300 . ? C25 H25 0.9300 . ? C10 C11 1.382(3) . ? C10 H10 0.9300 . ? C14 C13 1.378(3) . ? C14 H14 0.9300 . ? C11 H11 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C13 H13 0.9300 . ? C22 C21 1.382(3) . ? C22 H22 0.9300 . ? C18 C19 1.381(3) . ? C18 H18 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C20 C21 1.374(3) . ? C20 C19 1.381(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C19 H19 0.9300 . ? 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 C7 O1 C4 106.05(12) . . ? C3 O2 C2 116.11(13) . . ? C7 O4 C8 117.89(13) . . ? C15 O5 C16 116.34(14) . . ? C4 C5 C6 106.20(15) . . ? C4 C5 C23 125.81(15) . . ? C6 C5 C23 127.87(15) . . ? O4 C7 O1 118.49(14) . . ? O4 C7 C6 129.43(16) . . ? O1 C7 C6 112.08(14) . . ? O3 C3 O2 124.50(16) . . ? O3 C3 C4 123.86(15) . . ? O2 C3 C4 111.64(14) . . ? O6 C15 O5 123.33(16) . . ? O6 C15 C6 124.44(17) . . ? O5 C15 C6 112.22(15) . . ? C28 C23 C24 119.22(16) . . ? C28 C23 C5 121.29(15) . . ? C24 C23 C5 119.45(15) . . ? C27 C28 C23 120.29(17) . . ? C27 C28 H28 119.9 . . ? C23 C28 H28 119.9 . . ? C10 C9 C14 118.83(16) . . ? C10 C9 C8 123.14(16) . . ? C14 C9 C8 118.03(16) . . ? C7 C6 C5 105.45(15) . . ? C7 C6 C15 123.18(15) . . ? C5 C6 C15 131.25(15) . . ? C5 C4 O1 110.20(14) . . ? C5 C4 C3 136.09(16) . . ? O1 C4 C3 113.67(13) . . ? C22 C17 C18 119.05(18) . . ? C22 C17 C16 122.40(17) . . ? C18 C17 C16 118.54(17) . . ? O2 C2 C1 110.96(15) . . ? O2 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? O2 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C25 C24 C23 119.99(17) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? O4 C8 C9 108.23(14) . . ? O4 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? O4 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C26 C27 C28 120.23(18) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C11 C12 C13 119.35(18) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C25 C26 C27 119.83(17) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C25 C24 120.42(18) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C9 C10 C11 120.31(17) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C13 C14 C9 120.66(18) . . ? C13 C14 H14 119.7 . . ? C9 C14 H14 119.7 . . ? C12 C11 C10 120.64(18) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C12 C13 C14 120.21(18) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C21 C22 C17 120.26(18) . . ? C21 C22 H22 119.9 . . ? C17 C22 H22 119.9 . . ? C19 C18 C17 120.41(19) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? O5 C16 C17 109.09(15) . . ? O5 C16 H16A 109.9 . . ? C17 C16 H16A 109.9 . . ? O5 C16 H16B 109.9 . . ? C17 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? C21 C20 C19 119.53(19) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 120.5(2) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C18 C19 C20 120.23(19) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.162 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 930436'