# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _audit_creation_date 06-06-11 _publ_contact_author_name 'Catherine Guillou' _publ_contact_author_address ;Centre de Recherches de Gif Institut de Chimie des Substances Naturelles-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; _publ_contact_author_phone +3316982 _publ_contact_author_fax +33169077247 _publ_contact_author_email catherine.guillou@icsn.cnrs-gif.fr _publ_contact_letter ; ; _publ_requested_category FM _publ_section_title ; Routes to ................ .......................... .......................... ; loop_ _publ_author_name _publ_author_address C.Guillou ;Centre de Recherches de Gif Institut de Chimie des Substances Naturelles-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; L.Chabaud ;Centre de Recherches de Gif Institut de Chimie des Substances Naturelles-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; L.Duroure ;Centre de Recherches de Gif Institut de Chimie des Substances Naturelles-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; P.Retailleau '' T.Jousseaume '' E.Barre '' R.Araoz '' J.Molgo '' _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Beurskens,P.T., Beurskens, G., de Gelder, R. Garcia-Granda, S., Gould,R.O., Israel, R. and Smits, J.M.M. (1999). The DIRDIF-99 program system, Crystallography Laboratory, University of Nijmegen, The Netherlands. Coppens, P. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 255-270. Copenhagen: Munksgaard. Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). Mercury: visualization and analysis of crystal structures. J.Appl. Cryst. 39, 453-457. Nonius, B. V. (1999). COLLECT, data collection software. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Volume 276, Macromolecular Crystallography, part A, edited by C.W. Carter, Jr. & R.M. Sweet, 307-326, 1997, New York: Academic Press. Palatinus L., Chapuis G. (2007): Superflip - a computer program for the solution of crystal structures by charge flipping in arbitrary dimensions. J.Appl. Cryst. 40, 786-790. Sheldrick, G.M. (2008).Acta Cryst. A64, 112-122. Spek, A. L. (2003). J.Appl. Cryst. 36, 7-13. Welter, R. (2006). The Crystalbuilder Project Acta Cryst. A62, s252. Westrip, S. P. (2008). publCIF. In preparation. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; data_LC382 _database_code_depnum_ccdc_archive 'CCDC 828699' #TrackingRef 'Cif-lactone-OBC-Guillou-et-al.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; rac-7-hydroxy-2-oxaspiro[5.5]undec-8-en-1-one ; _chemical_name_common rac-7-hydroxy-2-oxaspiro(5.5)undec-8-en-1-one _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 O3' _chemical_formula_sum 'C10 H14 O3' _chemical_formula_weight 182.21 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 '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' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.1149(11) _cell_length_b 6.9784(8) _cell_length_c 14.9231(15) _cell_angle_alpha 90.00 _cell_angle_beta 98.171(7) _cell_angle_gamma 90.00 _cell_volume 939.58(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1259 _cell_measurement_theta_min 7.0 _cell_measurement_theta_max 71.3 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.775 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.739 _exptl_absorpt_process_details 'FS_ABSCOR (Rigaku, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku rapid II RAXIS conversion' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_type 'RAPID II large area curved imaging plate detector ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3666 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 7.02 _diffrn_reflns_theta_max 68.97 _reflns_number_total 1676 _reflns_number_gt 1173 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_structure_solution 'Superflip (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.0948P)^2^+0.0818P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1676 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1804 _refine_ls_wR_factor_gt 0.1617 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 O10 O -0.02665(19) 0.8004(2) 0.05606(11) 0.0886(6) Uani 1 1 d . A . O12 O 0.2116(2) 0.3596(3) 0.13632(12) 0.1064(7) Uani 1 1 d . . . H12 H 0.1337 0.3311 0.1045 0.160 Uiso 1 1 calc R . . O13 O 0.08325(18) 0.6705(2) -0.04810(10) 0.0877(6) Uani 1 1 d . A . C1 C 0.5035(3) 0.8159(5) 0.1114(2) 0.1212(12) Uani 1 1 d . . . H1A H 0.5757 0.8670 0.0758 0.145 Uiso 1 1 calc R . . H1B H 0.5066 0.8941 0.1653 0.145 Uiso 1 1 calc R . . C2 C 0.5451(3) 0.6180(6) 0.13823(19) 0.1170(11) Uani 1 1 d . . . H2 H 0.6424 0.5940 0.1638 0.140 Uiso 1 1 calc R . . C3 C 0.4523(3) 0.4743(5) 0.12795(15) 0.0990(9) Uani 1 1 d . . . H3 H 0.4880 0.3536 0.1462 0.119 Uiso 1 1 calc R . . C4 C 0.2924(2) 0.4914(4) 0.08870(13) 0.0790(7) Uani 1 1 d . . . H4 H 0.2813 0.4535 0.0249 0.095 Uiso 1 1 calc R . . C5 C 0.2382(2) 0.6991(3) 0.09462(13) 0.0684(6) Uani 1 1 d . A . C6 C 0.3502(3) 0.8301(4) 0.05656(17) 0.0928(8) Uani 1 1 d . . . H6A H 0.3557 0.7946 -0.0057 0.111 Uiso 1 1 calc R . . H6B H 0.3160 0.9616 0.0570 0.111 Uiso 1 1 calc R . . C7 C 0.2205(3) 0.7499(4) 0.19235(15) 0.0963(8) Uani 1 1 d . . . H7A H 0.1959 0.6342 0.2230 0.116 Uiso 0.708(13) 1 calc PR A 1 H7B H 0.3150 0.7956 0.2230 0.116 Uiso 0.708(13) 1 calc PR A 1 H7C H 0.2678 0.6499 0.2314 0.116 Uiso 0.292(13) 1 calc PR A 2 H7D H 0.2747 0.8676 0.2081 0.116 Uiso 0.292(13) 1 calc PR A 2 C8A C 0.1088(5) 0.8932(11) 0.2013(3) 0.0926(18) Uani 0.708(13) 1 d P A 1 H8A1 H 0.0948 0.9003 0.2645 0.111 Uiso 0.708(13) 1 calc PR A 1 H8A2 H 0.1457 1.0167 0.1848 0.111 Uiso 0.708(13) 1 calc PR A 1 C8B C 0.0775(15) 0.774(2) 0.2122(6) 0.089(4) Uani 0.292(13) 1 d P A 2 H8B1 H 0.0843 0.8489 0.2673 0.107 Uiso 0.292(13) 1 calc PR A 2 H8B2 H 0.0411 0.6481 0.2260 0.107 Uiso 0.292(13) 1 calc PR A 2 C9 C -0.0332(3) 0.8605(5) 0.1477(2) 0.1042(9) Uani 1 1 d . . . H9A H -0.0855 0.7634 0.1773 0.125 Uiso 0.708(13) 1 calc PR A 1 H9B H -0.0906 0.9777 0.1461 0.125 Uiso 0.708(13) 1 calc PR A 1 H9C H -0.0218 0.9986 0.1513 0.125 Uiso 0.292(13) 1 calc PR A 2 H9D H -0.1301 0.8292 0.1632 0.125 Uiso 0.292(13) 1 calc PR A 2 C11 C 0.0927(3) 0.7219(3) 0.03037(14) 0.0723(6) Uani 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 O10 0.0841(11) 0.0862(12) 0.0907(11) -0.0064(8) -0.0039(8) 0.0117(8) O12 0.1118(14) 0.0966(12) 0.0994(13) 0.0395(10) -0.0243(10) -0.0177(10) O13 0.1005(12) 0.0992(13) 0.0581(9) 0.0048(7) -0.0073(7) 0.0014(8) C1 0.0891(18) 0.160(3) 0.111(2) 0.044(2) 0.0016(15) -0.0382(18) C2 0.0769(16) 0.173(3) 0.0987(19) 0.046(2) 0.0049(14) -0.003(2) C3 0.0914(17) 0.120(2) 0.0825(16) 0.0203(15) 0.0021(12) 0.0184(17) C4 0.0878(14) 0.0871(16) 0.0585(10) 0.0088(11) -0.0016(9) 0.0053(12) C5 0.0742(13) 0.0743(14) 0.0546(11) 0.0062(9) 0.0014(9) -0.0063(10) C6 0.0922(17) 0.0992(19) 0.0845(16) 0.0245(13) 0.0042(12) -0.0175(14) C7 0.0997(18) 0.123(2) 0.0626(13) -0.0104(13) 0.0001(12) 0.0027(17) C8A 0.112(3) 0.095(4) 0.072(2) -0.011(2) 0.0178(19) -0.001(3) C8B 0.133(9) 0.072(8) 0.066(5) 0.012(4) 0.029(5) 0.002(6) C9 0.107(2) 0.113(2) 0.0930(18) -0.0089(16) 0.0167(15) 0.0154(16) C11 0.0852(15) 0.0669(13) 0.0614(12) 0.0097(9) -0.0017(10) -0.0051(11) _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 O10 C11 1.322(3) . ? O10 C9 1.439(3) . ? O12 C4 1.429(3) . ? O12 H12 0.8200 . ? O13 C11 1.216(2) . ? C1 C2 1.472(5) . ? C1 C6 1.519(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.306(4) . ? C2 H2 0.9300 . ? C3 C4 1.496(3) . ? C3 H3 0.9300 . ? C4 C5 1.538(3) . ? C4 H4 0.9800 . ? C5 C11 1.530(3) . ? C5 C7 1.532(3) . ? C5 C6 1.538(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8B 1.387(12) . ? C7 C8A 1.447(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C7 H7D 0.9700 . ? C8A C9 1.440(5) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C8B C9 1.426(11) . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C9 H9D 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 C11 O10 C9 122.88(19) . . ? C4 O12 H12 109.5 . . ? C2 C1 C6 112.9(3) . . ? C2 C1 H1A 109.0 . . ? C6 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? C6 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 123.4(3) . . ? C3 C2 H2 118.3 . . ? C1 C2 H2 118.3 . . ? C2 C3 C4 124.3(3) . . ? C2 C3 H3 117.9 . . ? C4 C3 H3 117.9 . . ? O12 C4 C3 107.26(18) . . ? O12 C4 C5 112.65(19) . . ? C3 C4 C5 110.8(2) . . ? O12 C4 H4 108.7 . . ? C3 C4 H4 108.7 . . ? C5 C4 H4 108.7 . . ? C11 C5 C7 111.93(19) . . ? C11 C5 C6 105.57(16) . . ? C7 C5 C6 112.3(2) . . ? C11 C5 C4 108.61(16) . . ? C7 C5 C4 110.56(18) . . ? C6 C5 C4 107.66(19) . . ? C1 C6 C5 111.76(19) . . ? C1 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? C1 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C8B C7 C8A 37.1(5) . . ? C8B C7 C5 117.4(5) . . ? C8A C7 C5 114.8(3) . . ? C8B C7 H7A 73.2 . . ? C8A C7 H7A 108.6 . . ? C5 C7 H7A 108.6 . . ? C8B C7 H7B 131.2 . . ? C8A C7 H7B 108.6 . . ? C5 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C8B C7 H7C 108.0 . . ? C8A C7 H7C 134.4 . . ? C5 C7 H7C 108.0 . . ? H7A C7 H7C 39.7 . . ? H7B C7 H7C 70.4 . . ? C8B C7 H7D 108.0 . . ? C8A C7 H7D 74.5 . . ? C5 C7 H7D 108.0 . . ? H7A C7 H7D 137.3 . . ? H7B C7 H7D 38.7 . . ? H7C C7 H7D 107.2 . . ? C9 C8A C7 115.3(4) . . ? C9 C8A H8A1 108.4 . . ? C7 C8A H8A1 108.4 . . ? C9 C8A H8A2 108.4 . . ? C7 C8A H8A2 108.4 . . ? H8A1 C8A H8A2 107.5 . . ? C7 C8B C9 120.2(7) . . ? C7 C8B H8B1 107.3 . . ? C9 C8B H8B1 107.3 . . ? C7 C8B H8B2 107.3 . . ? C9 C8B H8B2 107.3 . . ? H8B1 C8B H8B2 106.9 . . ? C8B C9 O10 113.4(5) . . ? C8B C9 C8A 36.7(5) . . ? O10 C9 C8A 114.8(3) . . ? C8B C9 H9A 75.1 . . ? O10 C9 H9A 108.6 . . ? C8A C9 H9A 108.6 . . ? C8B C9 H9B 134.5 . . ? O10 C9 H9B 108.6 . . ? C8A C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C8B C9 H9C 108.9 . . ? O10 C9 H9C 108.9 . . ? C8A C9 H9C 74.4 . . ? H9A C9 H9C 136.4 . . ? H9B C9 H9C 38.4 . . ? C8B C9 H9D 108.9 . . ? O10 C9 H9D 108.9 . . ? C8A C9 H9D 132.8 . . ? H9A C9 H9D 37.9 . . ? H9B C9 H9D 71.9 . . ? H9C C9 H9D 107.7 . . ? O13 C11 O10 116.92(19) . . ? O13 C11 C5 120.6(2) . . ? O10 C11 C5 122.46(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -9.6(5) . . . . ? C1 C2 C3 C4 -0.6(5) . . . . ? C2 C3 C4 O12 -144.1(3) . . . . ? C2 C3 C4 C5 -20.8(4) . . . . ? O12 C4 C5 C11 -76.3(2) . . . . ? C3 C4 C5 C11 163.49(18) . . . . ? O12 C4 C5 C7 46.8(2) . . . . ? C3 C4 C5 C7 -73.3(2) . . . . ? O12 C4 C5 C6 169.82(17) . . . . ? C3 C4 C5 C6 49.6(2) . . . . ? C2 C1 C6 C5 41.2(4) . . . . ? C11 C5 C6 C1 -177.4(2) . . . . ? C7 C5 C6 C1 60.4(3) . . . . ? C4 C5 C6 C1 -61.5(3) . . . . ? C11 C5 C7 C8B 11.3(8) . . . . ? C6 C5 C7 C8B 129.8(8) . . . . ? C4 C5 C7 C8B -109.9(8) . . . . ? C11 C5 C7 C8A -30.1(5) . . . . ? C6 C5 C7 C8A 88.5(4) . . . . ? C4 C5 C7 C8A -151.3(4) . . . . ? C8B C7 C8A C9 -54.2(7) . . . . ? C5 C7 C8A C9 49.1(7) . . . . ? C8A C7 C8B C9 58.9(9) . . . . ? C5 C7 C8B C9 -36.6(16) . . . . ? C7 C8B C9 O10 40.4(15) . . . . ? C7 C8B C9 C8A -60.2(11) . . . . ? C11 O10 C9 C8B -19.4(8) . . . . ? C11 O10 C9 C8A 21.0(5) . . . . ? C7 C8A C9 C8B 52.7(7) . . . . ? C7 C8A C9 O10 -43.7(7) . . . . ? C9 O10 C11 O13 177.4(2) . . . . ? C9 O10 C11 C5 -3.9(3) . . . . ? C7 C5 C11 O13 -173.1(2) . . . . ? C6 C5 C11 O13 64.5(3) . . . . ? C4 C5 C11 O13 -50.7(3) . . . . ? C7 C5 C11 O10 8.2(3) . . . . ? C6 C5 C11 O10 -114.2(2) . . . . ? C4 C5 C11 O10 130.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 68.97 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.188 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.037 #===END