# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name R.Stockman _publ_contact_author_name 'Robert Stockman' _publ_contact_author_email robert.stockman@nottingham.ac.uk data_biceto _database_code_depnum_ccdc_archive 'CCDC 839592' #TrackingRef 'BICETO.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H26 O5' _chemical_formula_sum 'C17 H26 O5' _chemical_formula_weight 310.38 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' _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 12.942(2) _cell_length_b 5.7874(10) _cell_length_c 22.755(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.764(3) _cell_angle_gamma 90.00 _cell_volume 1648.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4842 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 27.54 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.740 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details 'SADABS 2007/2' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% 0 _diffrn_reflns_number 10560 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2881 _reflns_number_gt 2745 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _refine_special_details ; CH3's refined as rigid rotors. ; _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^)+(0.0078P)^2^+8.2087P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2881 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1409 _refine_ls_R_factor_gt 0.1351 _refine_ls_wR_factor_ref 0.2285 _refine_ls_wR_factor_gt 0.2264 _refine_ls_goodness_of_fit_ref 1.401 _refine_ls_restrained_S_all 1.401 _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 C1 C 0.4534(4) 0.2614(10) 0.3038(2) 0.0279(13) Uani 1 1 d . . . O1 O 0.4332(3) 0.0840(7) 0.27455(18) 0.0371(10) Uani 1 1 d . . . C2 C 0.5538(4) 0.2857(11) 0.3536(3) 0.0345(14) Uani 1 1 d . . . H2A H 0.6005 0.4034 0.3419 0.041 Uiso 1 1 calc R . . H2B H 0.5928 0.1368 0.3594 0.041 Uiso 1 1 calc R . . C3 C 0.5285(4) 0.3570(10) 0.4128(2) 0.0285(13) Uani 1 1 d . . . H3A H 0.5960 0.3913 0.4436 0.034 Uiso 1 1 calc R . . H3B H 0.4928 0.2274 0.4281 0.034 Uiso 1 1 calc R . . C4 C 0.4562(4) 0.5697(10) 0.4040(2) 0.0262(12) Uani 1 1 d . . . H4A H 0.4946 0.7034 0.3925 0.031 Uiso 1 1 calc R . . H4B H 0.4386 0.6072 0.4428 0.031 Uiso 1 1 calc R . . C5 C 0.3527(4) 0.5276(9) 0.3545(2) 0.0226(12) Uani 1 1 d . . . H5A H 0.3140 0.3948 0.3673 0.027 Uiso 1 1 calc R . . C6 C 0.2794(4) 0.7404(9) 0.3456(2) 0.0218(12) Uani 1 1 d . . . H6A H 0.3204 0.8738 0.3351 0.026 Uiso 1 1 calc R . . C7 C 0.1763(4) 0.7089(10) 0.2923(2) 0.0276(13) Uani 1 1 d . . . H7A H 0.1389 0.8615 0.2853 0.033 Uiso 1 1 calc R . . C8 C 0.2098(4) 0.6462(11) 0.2347(2) 0.0295(14) Uani 1 1 d . . . H8A H 0.1451 0.6216 0.2011 0.035 Uiso 1 1 calc R . . H8B H 0.2501 0.7769 0.2233 0.035 Uiso 1 1 calc R . . C9 C 0.2782(4) 0.4313(11) 0.2424(2) 0.0306(13) Uani 1 1 d . . . H9A H 0.2987 0.3983 0.2042 0.037 Uiso 1 1 calc R . . H9B H 0.2369 0.2978 0.2515 0.037 Uiso 1 1 calc R . . C10 C 0.3785(4) 0.4645(9) 0.2942(2) 0.0232(12) Uani 1 1 d . . . H10A H 0.4181 0.5986 0.2828 0.028 Uiso 1 1 calc R . . C11 C 0.2474(4) 0.8022(9) 0.4029(2) 0.0181(11) Uani 1 1 d . . . O2 O 0.2341(3) 1.0303(6) 0.40657(16) 0.0215(8) Uani 1 1 d . . . O3 O 0.2321(3) 0.6668(6) 0.43955(15) 0.0234(8) Uani 1 1 d . . . C12 C 0.1943(4) 1.1125(9) 0.4570(2) 0.0265(13) Uani 1 1 d . . . H12A H 0.1425 0.9997 0.4655 0.032 Uiso 1 1 calc R . . H12B H 0.1567 1.2613 0.4459 0.032 Uiso 1 1 calc R . . C13 C 0.2844(5) 1.1445(11) 0.5127(3) 0.0370(15) Uani 1 1 d . . . H13A H 0.2565 1.2081 0.5455 0.056 Uiso 1 1 calc R . . H13B H 0.3371 1.2512 0.5037 0.056 Uiso 1 1 calc R . . H13C H 0.3184 0.9950 0.5253 0.056 Uiso 1 1 calc R . . C14 C 0.0977(4) 0.5318(10) 0.3064(2) 0.0279(13) Uani 1 1 d . . . H14A H 0.0535 0.4693 0.2675 0.034 Uiso 1 1 calc R . . H14B H 0.1388 0.4018 0.3293 0.034 Uiso 1 1 calc R . . C15 C 0.0244(4) 0.6275(10) 0.3425(2) 0.0222(12) Uani 1 1 d . . . O4 O -0.0170(3) 0.4591(7) 0.36856(16) 0.0292(9) Uani 1 1 d . . . O5 O 0.0029(3) 0.8293(8) 0.34599(19) 0.0383(11) Uani 1 1 d . . . C16 C -0.0928(5) 0.5272(11) 0.4023(3) 0.0341(14) Uani 1 1 d . . . H16A H -0.1584 0.5897 0.3744 0.041 Uiso 1 1 calc R . . H16B H -0.0615 0.6482 0.4324 0.041 Uiso 1 1 calc R . . C17 C -0.1186(5) 0.3170(12) 0.4340(3) 0.0443(17) Uani 1 1 d . . . H17A H -0.1700 0.3575 0.4574 0.067 Uiso 1 1 calc R . . H17B H -0.0531 0.2569 0.4615 0.067 Uiso 1 1 calc R . . H17C H -0.1497 0.1987 0.4038 0.067 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 0.042(3) 0.027(3) 0.024(3) -0.010(2) 0.025(2) -0.009(3) O1 0.046(2) 0.034(2) 0.040(2) -0.008(2) 0.027(2) -0.006(2) C2 0.031(3) 0.033(3) 0.043(4) -0.001(3) 0.015(3) 0.012(3) C3 0.028(3) 0.032(3) 0.023(3) 0.006(2) 0.002(2) 0.003(3) C4 0.029(3) 0.030(3) 0.021(3) -0.002(2) 0.007(2) 0.003(2) C5 0.025(3) 0.023(3) 0.020(3) 0.003(2) 0.006(2) 0.000(2) C6 0.015(2) 0.026(3) 0.024(3) 0.005(2) 0.005(2) -0.005(2) C7 0.027(3) 0.034(3) 0.022(3) 0.008(2) 0.005(2) 0.006(3) C8 0.021(3) 0.047(4) 0.020(3) 0.004(3) 0.005(2) -0.009(3) C9 0.032(3) 0.042(4) 0.021(3) -0.001(3) 0.013(2) -0.008(3) C10 0.025(3) 0.023(3) 0.025(3) -0.002(2) 0.012(2) -0.008(2) C11 0.011(2) 0.019(3) 0.022(3) 0.005(2) 0.001(2) -0.003(2) O2 0.0268(19) 0.0119(18) 0.0267(19) 0.0041(15) 0.0083(15) 0.0002(15) O3 0.035(2) 0.0174(19) 0.0212(18) 0.0024(16) 0.0134(16) -0.0001(16) C12 0.030(3) 0.015(3) 0.037(3) 0.001(2) 0.012(2) 0.009(2) C13 0.042(3) 0.032(3) 0.036(3) -0.005(3) 0.007(3) 0.008(3) C14 0.021(3) 0.037(3) 0.023(3) -0.003(3) 0.000(2) -0.003(2) C15 0.011(2) 0.030(3) 0.022(3) 0.005(2) -0.003(2) -0.002(2) O4 0.030(2) 0.032(2) 0.030(2) -0.0013(18) 0.0147(17) -0.0028(18) O5 0.034(2) 0.038(3) 0.044(3) 0.010(2) 0.0133(19) 0.007(2) C16 0.031(3) 0.045(4) 0.030(3) -0.002(3) 0.016(3) -0.001(3) C17 0.054(4) 0.051(4) 0.036(3) 0.001(3) 0.025(3) -0.001(3) _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 1.216(6) . ? C1 C2 1.497(8) . ? C1 C10 1.504(8) . ? C2 C3 1.524(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.528(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.535(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.536(7) . ? C5 C10 1.537(7) . ? C5 H5A 1.0000 . ? C6 C11 1.508(7) . ? C6 C7 1.568(7) . ? C6 H6A 1.0000 . ? C7 C8 1.527(7) . ? C7 C14 1.534(8) . ? C7 H7A 1.0000 . ? C8 C9 1.511(8) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.526(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 1.0000 . ? C11 O3 1.197(6) . ? C11 O2 1.336(6) . ? O2 C12 1.452(6) . ? C12 C13 1.499(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.509(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O5 1.209(7) . ? C15 O4 1.323(6) . ? O4 C16 1.447(6) . ? C16 C17 1.495(9) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C2 121.2(5) . . ? O1 C1 C10 122.7(5) . . ? C2 C1 C10 116.1(5) . . ? C1 C2 C3 110.7(4) . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 111.4(4) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 111.1(4) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 111.3(4) . . ? C4 C5 C10 110.2(4) . . ? C6 C5 C10 109.9(4) . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5A 108.4 . . ? C10 C5 H5A 108.4 . . ? C11 C6 C5 111.9(4) . . ? C11 C6 C7 109.2(4) . . ? C5 C6 C7 112.6(4) . . ? C11 C6 H6A 107.7 . . ? C5 C6 H6A 107.7 . . ? C7 C6 H6A 107.7 . . ? C8 C7 C14 111.6(5) . . ? C8 C7 C6 108.6(4) . . ? C14 C7 C6 113.3(4) . . ? C8 C7 H7A 107.7 . . ? C14 C7 H7A 107.7 . . ? C6 C7 H7A 107.7 . . ? C9 C8 C7 112.4(4) . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 110.1(5) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C1 C10 C9 113.8(5) . . ? C1 C10 C5 109.5(4) . . ? C9 C10 C5 112.5(4) . . ? C1 C10 H10A 106.8 . . ? C9 C10 H10A 106.8 . . ? C5 C10 H10A 106.8 . . ? O3 C11 O2 123.8(5) . . ? O3 C11 C6 125.3(5) . . ? O2 C11 C6 110.9(4) . . ? C11 O2 C12 116.8(4) . . ? O2 C12 C13 110.6(4) . . ? O2 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C7 114.2(5) . . ? C15 C14 H14A 108.7 . . ? C7 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? C7 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? O5 C15 O4 123.7(5) . . ? O5 C15 C14 125.3(5) . . ? O4 C15 C14 110.9(5) . . ? C15 O4 C16 116.4(4) . . ? O4 C16 C17 107.4(5) . . ? O4 C16 H16A 110.2 . . ? C17 C16 H16A 110.2 . . ? O4 C16 H16B 110.2 . . ? C17 C16 H16B 110.2 . . ? H16A C16 H16B 108.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 O1 C1 C2 C3 -125.7(6) . . . . ? C10 C1 C2 C3 52.3(6) . . . . ? C1 C2 C3 C4 -51.9(7) . . . . ? C2 C3 C4 C5 56.5(6) . . . . ? C3 C4 C5 C6 179.8(4) . . . . ? C3 C4 C5 C10 -58.0(6) . . . . ? C4 C5 C6 C11 -60.4(5) . . . . ? C10 C5 C6 C11 177.2(4) . . . . ? C4 C5 C6 C7 176.2(4) . . . . ? C10 C5 C6 C7 53.8(5) . . . . ? C11 C6 C7 C8 -180.0(5) . . . . ? C5 C6 C7 C8 -55.1(6) . . . . ? C11 C6 C7 C14 -55.3(6) . . . . ? C5 C6 C7 C14 69.6(6) . . . . ? C14 C7 C8 C9 -68.5(6) . . . . ? C6 C7 C8 C9 57.2(6) . . . . ? C7 C8 C9 C10 -58.6(6) . . . . ? O1 C1 C10 C9 -2.8(7) . . . . ? C2 C1 C10 C9 179.2(5) . . . . ? O1 C1 C10 C5 124.1(5) . . . . ? C2 C1 C10 C5 -53.8(6) . . . . ? C8 C9 C10 C1 -178.0(4) . . . . ? C8 C9 C10 C5 56.6(6) . . . . ? C4 C5 C10 C1 54.9(6) . . . . ? C6 C5 C10 C1 178.0(4) . . . . ? C4 C5 C10 C9 -177.4(5) . . . . ? C6 C5 C10 C9 -54.4(6) . . . . ? C5 C6 C11 O3 -34.3(7) . . . . ? C7 C6 C11 O3 91.0(6) . . . . ? C5 C6 C11 O2 148.0(4) . . . . ? C7 C6 C11 O2 -86.7(5) . . . . ? O3 C11 O2 C12 -2.8(7) . . . . ? C6 C11 O2 C12 174.9(4) . . . . ? C11 O2 C12 C13 85.3(6) . . . . ? C8 C7 C14 C15 -153.6(4) . . . . ? C6 C7 C14 C15 83.4(6) . . . . ? C7 C14 C15 O5 21.4(7) . . . . ? C7 C14 C15 O4 -160.9(4) . . . . ? O5 C15 O4 C16 0.6(7) . . . . ? C14 C15 O4 C16 -177.2(4) . . . . ? C15 O4 C16 C17 -173.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.317 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.075