# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_fagn2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O3' _chemical_formula_sum 'C16 H18 O3' _chemical_formula_weight 258.30 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 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 10.0252(6) _cell_length_b 6.6763(4) _cell_length_c 20.0548(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.2240(10) _cell_angle_gamma 90.00 _cell_volume 1340.17(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2216 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 22.7 _cell_measurement_wavelength 0.71073 _exptl_crystal_description plate _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details 'Sheldrick, 2004' _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 'Bruker-AXS SMART APEX' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 14597 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 29.99 _reflns_number_total 3906 _reflns_number_gt 2207 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-AXS SMART APEX' _computing_cell_refinement 'GLOBAL (Bruker)' _computing_data_reduction 'SAINTPLUS (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publ routines (Farrugia, 1999)' _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^)+(0.0646P)^2^+0.1037P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3906 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1102 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1469 _refine_ls_wR_factor_gt 0.1253 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.49575(12) 0.63915(19) 0.79417(7) 0.0652(4) Uani 1 d . . . O2 O 0.09843(12) 0.32357(19) 0.89234(6) 0.0649(4) Uani 1 d . . . O3 O 0.32643(14) -0.4701(2) 1.02607(7) 0.0763(4) Uani 1 d . . . C1 C 0.31581(18) 0.7137(3) 0.71143(9) 0.0560(5) Uani 1 d . . . C2 C 0.37932(16) 0.6344(2) 0.77571(8) 0.0476(4) Uani 1 d . . . C3 C 0.26764(16) 0.5368(2) 0.81281(8) 0.0461(4) Uani 1 d . . . C4 C 0.15132(17) 0.5500(3) 0.75986(9) 0.0542(4) Uani 1 d . . . C5 C 0.1789(2) 0.4181(3) 0.70057(10) 0.0661(5) Uani 1 d . . . C6 C 0.2918(2) 0.5270(3) 0.66769(10) 0.0648(5) Uani 1 d . . . C7 C 0.17451(19) 0.7602(3) 0.73178(11) 0.0606(5) Uani 1 d . . . C8 C 0.30910(18) 0.3383(3) 0.84387(9) 0.0488(4) Uani 1 d . . . C9 C 0.20612(16) 0.2440(2) 0.88598(7) 0.0452(4) Uani 1 d . . . C10 C 0.23912(15) 0.0509(2) 0.92036(7) 0.0418(4) Uani 1 d . . . C11 C 0.13798(17) -0.0538(3) 0.94951(8) 0.0493(4) Uani 1 d . . . C12 C 0.16210(18) -0.2275(3) 0.98516(9) 0.0527(4) Uani 1 d . . . C13 C 0.29052(17) -0.3004(3) 0.99163(8) 0.0514(4) Uani 1 d . . . C14 C 0.39284(18) -0.2020(3) 0.96180(9) 0.0566(5) Uani 1 d . . . C15 C 0.36686(17) -0.0288(3) 0.92658(8) 0.0503(4) Uani 1 d . . . C16 C 0.2283(3) -0.5725(4) 1.06118(14) 0.0794(7) Uani 1 d . . . H1 H 0.3643(18) 0.816(3) 0.6912(9) 0.065(5) Uiso 1 d . . . H3 H 0.2461(17) 0.630(3) 0.8490(9) 0.057(5) Uiso 1 d . . . H4 H 0.0680(18) 0.538(3) 0.7774(9) 0.055(5) Uiso 1 d . . . H6A H 0.368(2) 0.443(4) 0.6663(11) 0.086(7) Uiso 1 d . . . H6B H 0.2618(19) 0.568(3) 0.6209(11) 0.075(6) Uiso 1 d . . . H5A H 0.098(2) 0.409(3) 0.6713(12) 0.090(7) Uiso 1 d . . . H5B H 0.201(2) 0.277(4) 0.7145(11) 0.087(7) Uiso 1 d . . . H7A H 0.173(2) 0.868(3) 0.7648(11) 0.076(6) Uiso 1 d . . . H7B H 0.1122(19) 0.786(3) 0.6918(10) 0.068(6) Uiso 1 d . . . H8A H 0.3363(17) 0.243(3) 0.8072(10) 0.065(5) Uiso 1 d . . . H8B H 0.389(2) 0.361(3) 0.8740(10) 0.067(6) Uiso 1 d . . . H11 H 0.0519(19) -0.004(3) 0.9457(9) 0.060(5) Uiso 1 d . . . H12 H 0.0919(19) -0.295(3) 1.0049(9) 0.063(5) Uiso 1 d . . . H14 H 0.4772(19) -0.259(3) 0.9667(9) 0.066(5) Uiso 1 d . . . H15 H 0.4360(18) 0.036(3) 0.9067(9) 0.057(5) Uiso 1 d . . . H16A H 0.186(2) -0.484(4) 1.0921(13) 0.101(8) Uiso 1 d . . . H16B H 0.280(3) -0.671(5) 1.0848(15) 0.125(10) Uiso 1 d . . . H16C H 0.158(3) -0.632(4) 1.0304(14) 0.108(9) Uiso 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 O1 0.0444(7) 0.0628(8) 0.0873(9) 0.0086(7) -0.0060(6) -0.0100(6) O2 0.0540(7) 0.0696(9) 0.0731(9) 0.0177(7) 0.0227(6) 0.0138(6) O3 0.0781(10) 0.0701(9) 0.0814(9) 0.0311(8) 0.0113(7) 0.0112(7) C1 0.0486(9) 0.0531(10) 0.0670(12) 0.0190(9) 0.0086(8) -0.0031(8) C2 0.0438(9) 0.0393(8) 0.0595(10) -0.0001(7) 0.0015(7) -0.0039(7) C3 0.0476(9) 0.0470(9) 0.0441(9) -0.0032(7) 0.0061(7) -0.0013(7) C4 0.0380(9) 0.0685(12) 0.0564(10) 0.0084(9) 0.0057(8) -0.0053(8) C5 0.0724(14) 0.0661(13) 0.0582(11) -0.0007(10) -0.0106(10) -0.0084(10) C6 0.0720(13) 0.0726(13) 0.0499(11) 0.0072(9) 0.0047(9) 0.0122(11) C7 0.0543(11) 0.0568(12) 0.0706(13) 0.0094(10) 0.0028(9) 0.0123(9) C8 0.0457(9) 0.0520(10) 0.0491(9) 0.0061(8) 0.0081(8) 0.0003(7) C9 0.0448(9) 0.0515(10) 0.0397(8) -0.0015(7) 0.0064(6) -0.0003(7) C10 0.0425(8) 0.0481(9) 0.0352(7) -0.0035(7) 0.0060(6) -0.0032(7) C11 0.0431(9) 0.0565(10) 0.0491(9) 0.0020(8) 0.0101(7) 0.0020(8) C12 0.0549(11) 0.0525(10) 0.0523(10) 0.0052(8) 0.0162(8) -0.0049(8) C13 0.0602(11) 0.0518(10) 0.0419(9) 0.0037(7) 0.0015(7) 0.0020(8) C14 0.0449(10) 0.0634(11) 0.0611(11) 0.0076(9) -0.0001(8) 0.0049(8) C15 0.0418(9) 0.0568(10) 0.0527(10) 0.0042(8) 0.0064(7) -0.0035(8) C16 0.106(2) 0.0658(14) 0.0679(14) 0.0215(12) 0.0219(15) 0.0038(14) _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 C2 1.2051(19) . ? O2 C9 1.2164(18) . ? O3 C13 1.364(2) . ? O3 C16 1.418(3) . ? C1 C2 1.502(2) . ? C1 C7 1.528(3) . ? C1 C6 1.536(3) . ? C1 H1 0.944(19) . ? C2 C3 1.525(2) . ? C3 C8 1.513(2) . ? C3 C4 1.535(2) . ? C3 H3 0.989(18) . ? C4 C5 1.517(3) . ? C4 C7 1.534(3) . ? C4 H4 0.928(18) . ? C5 C6 1.526(3) . ? C5 H5A 0.97(2) . ? C5 H5B 1.00(2) . ? C6 H6A 0.95(2) . ? C6 H6B 1.01(2) . ? C7 H7A 0.98(2) . ? C7 H7B 1.00(2) . ? C8 C9 1.508(2) . ? C8 H8A 1.020(19) . ? C8 H8B 0.99(2) . ? C9 C10 1.491(2) . ? C10 C15 1.386(2) . ? C10 C11 1.388(2) . ? C11 C12 1.376(2) . ? C11 H11 0.925(19) . ? C12 C13 1.376(2) . ? C12 H12 0.942(19) . ? C13 C14 1.382(2) . ? C14 C15 1.372(3) . ? C14 H14 0.927(19) . ? C15 H15 0.925(19) . ? C16 H16A 0.97(3) . ? C16 H16B 0.95(3) . ? C16 H16C 0.99(3) . ? 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 C13 O3 C16 118.75(17) . . ? C2 C1 C7 101.37(15) . . ? C2 C1 C6 104.43(15) . . ? C7 C1 C6 101.50(16) . . ? C2 C1 H1 114.9(11) . . ? C7 C1 H1 118.4(11) . . ? C6 C1 H1 114.2(11) . . ? O1 C2 C1 127.66(16) . . ? O1 C2 C3 125.91(15) . . ? C1 C2 C3 106.38(14) . . ? C8 C3 C2 112.51(14) . . ? C8 C3 C4 121.04(15) . . ? C2 C3 C4 100.83(13) . . ? C8 C3 H3 108.3(10) . . ? C2 C3 H3 106.6(10) . . ? C4 C3 H3 106.5(10) . . ? C5 C4 C7 101.83(16) . . ? C5 C4 C3 110.13(16) . . ? C7 C4 C3 100.46(14) . . ? C5 C4 H4 116.9(11) . . ? C7 C4 H4 112.2(11) . . ? C3 C4 H4 113.5(11) . . ? C4 C5 C6 103.55(16) . . ? C4 C5 H5A 109.1(14) . . ? C6 C5 H5A 112.3(13) . . ? C4 C5 H5B 111.9(13) . . ? C6 C5 H5B 114.2(12) . . ? H5A C5 H5B 105.9(18) . . ? C5 C6 C1 103.66(16) . . ? C5 C6 H6A 110.5(14) . . ? C1 C6 H6A 113.2(14) . . ? C5 C6 H6B 110.0(11) . . ? C1 C6 H6B 110.0(12) . . ? H6A C6 H6B 109.3(18) . . ? C1 C7 C4 94.26(14) . . ? C1 C7 H7A 112.2(13) . . ? C4 C7 H7A 114.6(12) . . ? C1 C7 H7B 111.5(11) . . ? C4 C7 H7B 110.4(11) . . ? H7A C7 H7B 112.6(17) . . ? C9 C8 C3 114.55(14) . . ? C9 C8 H8A 111.3(10) . . ? C3 C8 H8A 109.1(10) . . ? C9 C8 H8B 106.1(11) . . ? C3 C8 H8B 108.2(11) . . ? H8A C8 H8B 107.2(15) . . ? O2 C9 C10 120.30(14) . . ? O2 C9 C8 121.08(15) . . ? C10 C9 C8 118.62(13) . . ? C15 C10 C11 117.52(15) . . ? C15 C10 C9 123.62(14) . . ? C11 C10 C9 118.83(14) . . ? C12 C11 C10 122.14(16) . . ? C12 C11 H11 119.0(11) . . ? C10 C11 H11 118.8(11) . . ? C13 C12 C11 118.89(16) . . ? C13 C12 H12 120.6(11) . . ? C11 C12 H12 120.5(11) . . ? O3 C13 C12 124.08(16) . . ? O3 C13 C14 115.62(16) . . ? C12 C13 C14 120.29(16) . . ? C15 C14 C13 119.94(17) . . ? C15 C14 H14 123.0(12) . . ? C13 C14 H14 117.1(12) . . ? C14 C15 C10 121.17(16) . . ? C14 C15 H15 119.2(11) . . ? C10 C15 H15 119.6(11) . . ? O3 C16 H16A 111.4(15) . . ? O3 C16 H16B 102.2(18) . . ? H16A C16 H16B 111(2) . . ? O3 C16 H16C 112.0(15) . . ? H16A C16 H16C 108(2) . . ? H16B C16 H16C 112(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 C7 C1 C2 O1 -152.55(18) . . . . ? C6 C1 C2 O1 102.3(2) . . . . ? C7 C1 C2 C3 29.77(18) . . . . ? C6 C1 C2 C3 -75.41(16) . . . . ? O1 C2 C3 C8 -40.8(2) . . . . ? C1 C2 C3 C8 136.98(16) . . . . ? O1 C2 C3 C4 -171.12(17) . . . . ? C1 C2 C3 C4 6.61(17) . . . . ? C8 C3 C4 C5 -58.4(2) . . . . ? C2 C3 C4 C5 66.33(17) . . . . ? C8 C3 C4 C7 -165.27(15) . . . . ? C2 C3 C4 C7 -40.51(16) . . . . ? C7 C4 C5 C6 35.6(2) . . . . ? C3 C4 C5 C6 -70.3(2) . . . . ? C4 C5 C6 C1 -0.9(2) . . . . ? C2 C1 C6 C5 70.85(19) . . . . ? C7 C1 C6 C5 -34.23(19) . . . . ? C2 C1 C7 C4 -53.13(17) . . . . ? C6 C1 C7 C4 54.35(17) . . . . ? C5 C4 C7 C1 -55.37(18) . . . . ? C3 C4 C7 C1 57.97(17) . . . . ? C2 C3 C8 C9 175.12(14) . . . . ? C4 C3 C8 C9 -65.7(2) . . . . ? C3 C8 C9 O2 1.3(2) . . . . ? C3 C8 C9 C10 -178.26(14) . . . . ? O2 C9 C10 C15 -166.81(16) . . . . ? C8 C9 C10 C15 12.8(2) . . . . ? O2 C9 C10 C11 11.4(2) . . . . ? C8 C9 C10 C11 -169.03(15) . . . . ? C15 C10 C11 C12 1.9(2) . . . . ? C9 C10 C11 C12 -176.45(15) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C16 O3 C13 C12 -4.2(3) . . . . ? C16 O3 C13 C14 176.4(2) . . . . ? C11 C12 C13 O3 179.57(17) . . . . ? C11 C12 C13 C14 -1.0(3) . . . . ? O3 C13 C14 C15 -179.37(17) . . . . ? C12 C13 C14 C15 1.2(3) . . . . ? C13 C14 C15 C10 0.2(3) . . . . ? C11 C10 C15 C14 -1.7(2) . . . . ? C9 C10 C15 C14 176.53(16) . . . . ? _diffrn_measured_fraction_theta_max 1 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 1 _refine_diff_density_max 0.259 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.037