# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author 'C. Marson' _publ_contact_author_email C.M.MARSON@UCL.AC.UK _publ_contact_author_address ; Department of Chemistry University College London 20 Gordon Street London WC1H 0AJ UNITED KINGDOM ; loop_ _publ_author_name C.Marson S.J.Coles D.T.Davies E.Edaan M.Hursthouse J.M.Morrell _publ_section_title ; The first catalytic asymmetric protocol for the enantioselective synthesis of 3(2H)-furanones ; data_5src0001 _database_code_depnum_ccdc_archive 'CCDC 260551' _audit_creation_date 2005-01-11T20:05:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C14 H16 O3' _chemical_formula_weight 232.27 _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.2521(3) _cell_length_b 9.3237(17) _cell_length_c 20.809(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1213.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.9705 _exptl_absorpt_correction_T_max 0.9895 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number none _diffrn_standards_decay_% negligible _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_unetI/netI 0.0188 _diffrn_reflns_number 27007 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 2773 _reflns_number_gt 2695 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0887P)^2^+0.1209P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.037(11) _refine_ls_number_reflns 2773 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(8) _refine_diff_density_max 0.222 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.06108(19) 0.25320(13) 0.10894(5) 0.0172(3) Uani 1 1 d . . . C2 C -0.02611(19) 0.40121(13) 0.09119(6) 0.0182(2) Uani 1 1 d . . . C3 C -0.1612(2) 0.44441(12) 0.14328(6) 0.0198(3) Uani 1 1 d . . . H3 H -0.2373 0.5323 0.1466 0.024 Uiso 1 1 calc R . . C4 C -0.16036(19) 0.33647(13) 0.18691(6) 0.0178(3) Uani 1 1 d . . . C5 C 0.3014(2) 0.26072(15) 0.11874(6) 0.0231(3) Uani 1 1 d . . . H5A H 0.336 0.3427 0.1463 0.035 Uiso 1 1 calc R . . H5B H 0.3722 0.2723 0.077 0.035 Uiso 1 1 calc R . . H5C H 0.3511 0.1721 0.1392 0.035 Uiso 1 1 calc R . . C6 C -0.01273(19) 0.14065(13) 0.06059(5) 0.0170(2) Uani 1 1 d . . . H6 H 0.0388 0.17 0.017 0.02 Uiso 1 1 calc R . . C7 C 0.0685(2) -0.00996(13) 0.07409(6) 0.0218(3) Uani 1 1 d . . . H7A H 0.0108 -0.0431 0.1158 0.026 Uiso 1 1 calc R . . H7B H 0.2265 -0.0079 0.0775 0.026 Uiso 1 1 calc R . . C8 C 0.0038(2) -0.11525(14) 0.02181(7) 0.0270(3) Uani 1 1 d . . . H8A H -0.1522 -0.1147 0.0171 0.041 Uiso 1 1 calc R . . H8B H 0.0515 -0.2118 0.0336 0.041 Uiso 1 1 calc R . . H8C H 0.0702 -0.0871 -0.0189 0.041 Uiso 1 1 calc R . . C9 C -0.2738(2) 0.32514(13) 0.24828(6) 0.0182(3) Uani 1 1 d . . . C10 C -0.2255(2) 0.21464(14) 0.29127(6) 0.0211(3) Uani 1 1 d . . . H10 H -0.1165 0.1472 0.2814 0.025 Uiso 1 1 calc R . . C11 C -0.3385(2) 0.20414(14) 0.34874(6) 0.0250(3) Uani 1 1 d . . . H11 H -0.3047 0.1302 0.3785 0.03 Uiso 1 1 calc R . . C12 C -0.4999(2) 0.30115(14) 0.36275(6) 0.0255(3) Uani 1 1 d . . . H12 H -0.5782 0.2922 0.4017 0.031 Uiso 1 1 calc R . . C13 C -0.5477(2) 0.41146(15) 0.32020(6) 0.0248(3) Uani 1 1 d . . . H13 H -0.6581 0.478 0.33 0.03 Uiso 1 1 calc R . . C14 C -0.4335(2) 0.42368(13) 0.26350(6) 0.0218(3) Uani 1 1 d . . . H14 H -0.4643 0.5 0.2347 0.026 Uiso 1 1 calc R . . O1 O -0.03766(14) 0.22301(9) 0.17113(4) 0.0176(2) Uani 1 1 d . . . O2 O 0.02104(16) 0.46466(10) 0.04143(4) 0.0232(2) Uani 1 1 d . . . O3 O -0.23970(14) 0.14826(10) 0.06091(4) 0.0215(2) Uani 1 1 d . . . H3A H -0.2883 0.1047 0.0287 0.032 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 0.0165(6) 0.0201(5) 0.0151(5) 0.0002(4) 0.0008(4) 0.0004(4) C2 0.0179(5) 0.0180(5) 0.0188(5) -0.0011(4) -0.0008(4) 0.0000(4) C3 0.0210(6) 0.0184(5) 0.0199(5) -0.0014(4) 0.0022(5) 0.0023(4) C4 0.0161(5) 0.0194(5) 0.0180(5) -0.0028(4) -0.0014(4) 0.0003(5) C5 0.0172(6) 0.0267(6) 0.0256(6) -0.0011(5) -0.0031(5) -0.0003(5) C6 0.0147(5) 0.0208(5) 0.0155(5) 0.0002(4) -0.0001(4) 0.0014(4) C7 0.0237(6) 0.0206(6) 0.0212(6) -0.0022(5) -0.0020(5) 0.0039(5) C8 0.0311(7) 0.0216(6) 0.0284(6) -0.0060(5) -0.0010(6) 0.0023(5) C9 0.0184(6) 0.0203(6) 0.0158(5) -0.0029(4) -0.0007(4) -0.0017(5) C10 0.0246(6) 0.0192(5) 0.0194(6) -0.0018(5) 0.0001(5) -0.0007(5) C11 0.0353(7) 0.0222(6) 0.0175(5) 0.0003(5) -0.0001(5) -0.0036(5) C12 0.0299(7) 0.0275(6) 0.0190(5) -0.0035(5) 0.0059(5) -0.0079(5) C13 0.0249(6) 0.0264(6) 0.0230(6) -0.0048(5) 0.0034(5) 0.0000(5) C14 0.0242(6) 0.0222(6) 0.0190(6) -0.0014(5) 0.0006(4) 0.0020(5) O1 0.0201(4) 0.0184(4) 0.0142(4) -0.0004(3) 0.0011(3) 0.0036(3) O2 0.0258(5) 0.0223(4) 0.0215(4) 0.0031(3) 0.0051(4) 0.0022(4) O3 0.0158(4) 0.0263(5) 0.0225(4) -0.0050(4) -0.0022(3) 0.0028(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.4612(14) . ? C1 C5 1.5178(16) . ? C1 C6 1.5252(16) . ? C1 C2 1.5290(17) . ? C2 O2 1.2285(15) . ? C2 C3 1.4322(17) . ? C3 C4 1.3555(17) . ? C3 H3 0.95 . ? C4 O1 1.3474(14) . ? C4 C9 1.4645(17) . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 O3 1.4208(15) . ? C6 C7 1.5196(16) . ? C6 H6 1 . ? C7 C8 1.5203(17) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 C14 1.3935(18) . ? C9 C10 1.3973(17) . ? C10 C11 1.3923(18) . ? C10 H10 0.95 . ? C11 C12 1.386(2) . ? C11 H11 0.95 . ? C12 C13 1.3897(19) . ? C12 H12 0.95 . ? C13 C14 1.3839(18) . ? C13 H13 0.95 . ? C14 H14 0.95 . ? O3 H3A 0.84 . ? 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 O1 C1 C5 107.95(10) . . ? O1 C1 C6 108.89(9) . . ? C5 C1 C6 114.83(10) . . ? O1 C1 C2 103.72(9) . . ? C5 C1 C2 110.10(10) . . ? C6 C1 C2 110.72(9) . . ? O2 C2 C3 130.09(12) . . ? O2 C2 C1 123.56(11) . . ? C3 C2 C1 106.34(10) . . ? C4 C3 C2 107.20(10) . . ? C4 C3 H3 126.4 . . ? C2 C3 H3 126.4 . . ? O1 C4 C3 114.96(10) . . ? O1 C4 C9 115.57(10) . . ? C3 C4 C9 129.47(11) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O3 C6 C7 112.29(10) . . ? O3 C6 C1 105.35(9) . . ? C7 C6 C1 114.37(10) . . ? O3 C6 H6 108.2 . . ? C7 C6 H6 108.2 . . ? C1 C6 H6 108.2 . . ? C6 C7 C8 112.05(10) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? 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 . . ? C14 C9 C10 119.69(11) . . ? C14 C9 C4 119.84(11) . . ? C10 C9 C4 120.46(11) . . ? C11 C10 C9 119.49(12) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 120.26(12) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.38(12) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 119.54(13) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C9 120.62(12) . . ? C13 C14 H14 119.7 . . ? C9 C14 H14 119.7 . . ? C4 O1 C1 107.77(9) . . ? C6 O3 H3A 109.5 . . ?