# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 203/358 data_m20 _audit_creation_method SHELXL-97 _publ_contact_author_email 'a.r.kennedy@strath.ac.uk' _publ_contact_author_phone '0141 548 4241' _publ_contact_author_address ; Dept. of P & A Chemistry University of Strathclyde Glasgow G1 1XL ; _chemical_name_common Alboatrin _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 O3' _chemical_formula_weight 234.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.886(4) _cell_length_b 13.659(6) _cell_length_c 10.369(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.05(4) _cell_angle_gamma 90.00 _cell_volume 1246.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 11.77 _cell_measurement_theta_max 15.28 _exptl_crystal_description rhomb _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S Diffractometer' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4049 _diffrn_reflns_av_R_equivalents 0.0692 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 24.09 _reflns_number_total 1973 _reflns_number_gt 1251 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection ; MSC/Rigaku diffractometer control software ; _computing_cell_refinement ; MSC/Rigaku diffractometer control software ; _computing_data_reduction 'TeXsan' _computing_structure_solution 'SAPI' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0000P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1973 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0868 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0187(2) -0.05850(15) 0.2755(2) 0.0774(7) Uani 1 d . . . H1 H -0.0038 -0.0003 0.2764 0.093 Uiso 1 calc R . . O2 O 0.4344(2) -0.27014(13) 0.3291(3) 0.0872(8) Uani 1 d . . . O3 O 0.5808(2) -0.36625(13) 0.22033(18) 0.0668(6) Uani 1 d . . . C1 C 0.1735(3) -0.06807(19) 0.2913(3) 0.0528(6) Uani 1 d . . . C2 C 0.2311(3) -0.16150(18) 0.3005(2) 0.0541(7) Uani 1 d . . . H2 H 0.1663 -0.2153 0.2959 0.065 Uiso 1 calc R . . C3 C 0.3870(3) -0.17429(17) 0.3166(2) 0.0509(6) Uani 1 d . . . C4 C 0.4882(3) -0.09672(17) 0.3254(2) 0.0492(6) Uani 1 d . . . C5 C 0.4272(3) -0.00193(18) 0.3166(2) 0.0504(6) Uani 1 d . . . C6 C 0.2708(3) 0.01151(19) 0.2990(2) 0.0547(7) Uani 1 d . . . H6 H 0.2310 0.0746 0.2924 0.066 Uiso 1 calc R . . C7 C 0.5309(3) 0.08585(18) 0.3275(3) 0.0664(8) Uani 1 d . . . H7A H 0.4713 0.1446 0.3265 0.100 Uiso 1 calc R . . H7B H 0.5878 0.0866 0.2553 0.100 Uiso 1 calc R . . H7C H 0.5996 0.0824 0.4075 0.100 Uiso 1 calc R . . C8 C 0.6556(3) -0.1180(2) 0.3460(3) 0.0619(7) Uani 1 d . . . H8A H 0.6922 -0.1193 0.4386 0.074 Uiso 1 calc R . . H8B H 0.7090 -0.0663 0.3070 0.074 Uiso 1 calc R . . C9 C 0.6892(3) -0.21635(17) 0.2854(3) 0.0556(7) Uani 1 d . . . H9 H 0.7941 -0.2336 0.3200 0.067 Uiso 1 calc R . . C10 C 0.5886(3) -0.29825(19) 0.3237(3) 0.0560(7) Uani 1 d . . . C11 C 0.6407(5) -0.3520(3) 0.4479(3) 0.0979(12) Uani 1 d . . . H11A H 0.5712 -0.4043 0.4581 0.147 Uiso 1 calc R . . H11B H 0.6438 -0.3076 0.5201 0.147 Uiso 1 calc R . . H11C H 0.7403 -0.3783 0.4452 0.147 Uiso 1 calc R . . C12 C 0.5707(4) -0.3085(3) 0.1027(3) 0.0867(10) Uani 1 d . . . H12A H 0.4673 -0.2863 0.0764 0.104 Uiso 1 calc R . . H12B H 0.6026 -0.3465 0.0324 0.104 Uiso 1 calc R . . C13 C 0.6756(3) -0.22244(19) 0.1357(3) 0.0620(7) Uani 1 d . . . H13 H 0.7756 -0.2410 0.1142 0.074 Uiso 1 calc R . . C14 C 0.6260(5) -0.1310(3) 0.0579(3) 0.1044(13) Uani 1 d . . . H14A H 0.6145 -0.1458 -0.0334 0.157 Uiso 1 calc R . . H14B H 0.7014 -0.0808 0.0775 0.157 Uiso 1 calc R . . H14C H 0.5307 -0.1085 0.0806 0.157 Uiso 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 0.0435(11) 0.0621(11) 0.1265(18) -0.0024(13) 0.0114(11) 0.0010(10) O2 0.0566(12) 0.0412(10) 0.171(2) 0.0003(12) 0.0405(13) 0.0021(10) O3 0.0771(14) 0.0520(10) 0.0730(12) -0.0104(9) 0.0167(10) -0.0082(10) C1 0.0374(14) 0.0562(14) 0.0648(16) -0.0048(13) 0.0075(11) -0.0016(12) C2 0.0481(16) 0.0462(14) 0.0703(17) -0.0059(12) 0.0162(12) -0.0065(12) C3 0.0467(16) 0.0395(13) 0.0682(16) -0.0064(11) 0.0136(12) 0.0018(11) C4 0.0427(14) 0.0477(14) 0.0572(14) -0.0061(11) 0.0071(11) -0.0047(12) C5 0.0509(16) 0.0440(13) 0.0565(14) -0.0040(11) 0.0079(11) -0.0060(12) C6 0.0494(16) 0.0452(13) 0.0698(17) 0.0005(12) 0.0089(12) 0.0020(12) C7 0.0633(19) 0.0466(14) 0.090(2) -0.0057(14) 0.0126(15) -0.0124(14) C8 0.0460(16) 0.0561(15) 0.0828(18) -0.0107(14) 0.0064(13) -0.0060(13) C9 0.0410(14) 0.0522(15) 0.0730(17) -0.0019(13) 0.0063(12) 0.0047(13) C10 0.0531(16) 0.0512(14) 0.0634(16) -0.0033(12) 0.0073(12) 0.0051(13) C11 0.118(3) 0.098(2) 0.072(2) 0.0195(19) -0.004(2) -0.014(2) C12 0.092(3) 0.105(2) 0.0613(18) 0.0020(18) 0.0054(16) -0.027(2) C13 0.0546(16) 0.0598(16) 0.0735(18) 0.0045(14) 0.0157(13) 0.0022(15) C14 0.140(4) 0.093(2) 0.087(2) 0.026(2) 0.038(2) 0.035(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 O1 C1 1.369(3) . ? O2 C3 1.376(3) . ? O2 C10 1.431(3) . ? O3 C10 1.413(3) . ? O3 C12 1.445(4) . ? C1 C2 1.373(4) . ? C1 C6 1.384(4) . ? C2 C3 1.383(4) . ? C3 C4 1.384(3) . ? C4 C5 1.401(4) . ? C4 C8 1.501(4) . ? C5 C6 1.388(4) . ? C5 C7 1.507(3) . ? C8 C9 1.530(4) . ? C9 C10 1.519(4) . ? C9 C13 1.542(4) . ? C10 C11 1.498(4) . ? C12 C13 1.509(4) . ? C13 C14 1.519(4) . ? 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 C3 O2 C10 122.3(2) . . ? C10 O3 C12 105.8(2) . . ? O1 C1 C2 117.1(2) . . ? O1 C1 C6 122.7(2) . . ? C2 C1 C6 120.2(2) . . ? C1 C2 C3 118.9(2) . . ? O2 C3 C2 114.8(2) . . ? O2 C3 C4 122.3(2) . . ? C2 C3 C4 122.8(2) . . ? C3 C4 C5 117.5(2) . . ? C3 C4 C8 118.8(2) . . ? C5 C4 C8 123.7(2) . . ? C6 C5 C4 120.1(2) . . ? C6 C5 C7 119.7(2) . . ? C4 C5 C7 120.2(2) . . ? C1 C6 C5 120.6(2) . . ? C4 C8 C9 111.0(2) . . ? C10 C9 C8 112.5(2) . . ? C10 C9 C13 104.9(2) . . ? C8 C9 C13 117.9(2) . . ? O3 C10 O2 105.1(2) . . ? O3 C10 C11 107.9(2) . . ? O2 C10 C11 106.2(3) . . ? O3 C10 C9 104.7(2) . . ? O2 C10 C9 114.5(2) . . ? C11 C10 C9 117.6(3) . . ? O3 C12 C13 105.7(2) . . ? C12 C13 C14 113.3(3) . . ? C12 C13 C9 103.2(2) . . ? C14 C13 C9 117.8(2) . . ? 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 -180.0(2) . . . . ? C6 C1 C2 C3 -0.4(4) . . . . ? C10 O2 C3 C2 168.9(2) . . . . ? C10 O2 C3 C4 -13.9(4) . . . . ? C1 C2 C3 O2 178.0(2) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? O2 C3 C4 C5 -177.4(2) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? O2 C3 C4 C8 1.6(4) . . . . ? C2 C3 C4 C8 178.6(2) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C8 C4 C5 C6 -179.2(2) . . . . ? C3 C4 C5 C7 179.1(2) . . . . ? C8 C4 C5 C7 0.2(4) . . . . ? O1 C1 C6 C5 179.3(2) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? C4 C5 C6 C1 0.7(4) . . . . ? C7 C5 C6 C1 -178.8(2) . . . . ? C3 C4 C8 C9 29.8(3) . . . . ? C5 C4 C8 C9 -151.3(2) . . . . ? C4 C8 C9 C10 -49.1(3) . . . . ? C4 C8 C9 C13 73.3(3) . . . . ? C12 O3 C10 O2 81.9(3) . . . . ? C12 O3 C10 C11 -165.1(3) . . . . ? C12 O3 C10 C9 -39.0(3) . . . . ? C3 O2 C10 O3 -122.1(3) . . . . ? C3 O2 C10 C11 123.7(3) . . . . ? C3 O2 C10 C9 -7.8(4) . . . . ? C8 C9 C10 O3 153.5(2) . . . . ? C13 C9 C10 O3 24.1(3) . . . . ? C8 C9 C10 O2 39.0(3) . . . . ? C13 C9 C10 O2 -90.4(3) . . . . ? C8 C9 C10 C11 -86.8(3) . . . . ? C13 C9 C10 C11 143.8(3) . . . . ? C10 O3 C12 C13 38.9(3) . . . . ? O3 C12 C13 C14 -150.5(3) . . . . ? O3 C12 C13 C9 -22.0(3) . . . . ? C10 C9 C13 C12 -1.0(3) . . . . ? C8 C9 C13 C12 -127.2(3) . . . . ? C10 C9 C13 C14 124.7(3) . . . . ? C8 C9 C13 C14 -1.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 24.09 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.166 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.036