# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Christopher S. P. McErlean' 'Caroline L. Nesbitt' _publ_contact_author_name 'Christopher S. P. McErlean' _publ_contact_author_email C.McErlean@chem.usyd.edu.au data_csm10pj1 _database_code_depnum_ccdc_archive 'CCDC 794007' #TrackingRef 'CSM10PJ1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 O4' _chemical_formula_sum 'C14 H16 O4' _chemical_formula_weight 248.27 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab ' _symmetry_int_tables_number 19 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.4822(4) _cell_length_b 8.8469(6) _cell_length_c 24.9538(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1210.27(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9970 _cell_measurement_theta_min 2.8225 _cell_measurement_theta_max 32.9315 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.927 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; SADABS Ver. 2008/1 (Bruker-AXS, 2008) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius FR591 Kappa APEX II' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18636 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 32.93 _reflns_number_total 2593 _reflns_number_gt 2485 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 Ver. 2009.11-0 (Bruker-AXS, 2009)' _computing_cell_refinement 'SAINT Ver. 7.68A (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT Ver. 7.68A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; X-Seed (Barbour, 2001), SHELXTL Ver. 6.14 (Bruker-AXS, 2003) ; _computing_publication_material 'modiCIFer-12162005 (Guzei, 2005)' _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^)+(0.0613P)^2^+0.1036P] 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 2593 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 O1 O 0.0748(2) 0.15208(10) 0.37743(3) 0.0370(2) Uani 1 1 d . . . O2 O 0.02592(16) 0.34345(9) 0.32005(3) 0.02514(15) Uani 1 1 d . . . O3 O 0.46580(17) 0.29305(10) 0.25596(3) 0.02959(19) Uani 1 1 d . . . O4 O 0.55230(17) 0.24951(8) 0.13982(3) 0.02483(16) Uani 1 1 d . . . C1 C 0.1633(2) 0.25584(11) 0.35285(4) 0.0243(2) Uani 1 1 d . . . C2 C 0.4243(2) 0.31012(11) 0.35184(4) 0.02397(19) Uani 1 1 d . . . H2A H 0.5400 0.2242 0.3517 0.029 Uiso 1 1 calc R . . H2B H 0.4602 0.3762 0.3829 0.029 Uiso 1 1 calc R . . C3 C 0.4351(2) 0.39740(11) 0.29967(4) 0.02226(18) Uani 1 1 d . . . H3 H 0.5604 0.4795 0.3000 0.027 Uiso 1 1 calc R . . C4 C 0.1767(2) 0.45658(11) 0.29349(4) 0.02182(17) Uani 1 1 d . . . H4 H 0.1560 0.5594 0.3095 0.026 Uiso 1 1 calc R . . C5 C 0.1313(2) 0.45586(14) 0.23372(4) 0.0286(2) Uani 1 1 d . . . H5A H 0.1755 0.5543 0.2175 0.034 Uiso 1 1 calc R . . H5B H -0.0419 0.4338 0.2257 0.034 Uiso 1 1 calc R . . C6 C 0.2983(2) 0.32894(11) 0.21300(4) 0.02270(18) Uani 1 1 d . . . H6 H 0.1973 0.2378 0.2046 0.027 Uiso 1 1 calc R . . C7 C 0.4351(2) 0.37688(11) 0.16314(4) 0.02303(18) Uani 1 1 d . . . H7A H 0.3200 0.4218 0.1371 0.028 Uiso 1 1 calc R . . H7B H 0.5582 0.4543 0.1725 0.028 Uiso 1 1 calc R . . C8 C 0.7119(3) 0.29487(12) 0.09712(5) 0.0319(3) Uani 1 1 d . . . H8A H 0.8606 0.3422 0.1121 0.038 Uiso 1 1 calc R . . H8B H 0.6290 0.3700 0.0740 0.038 Uiso 1 1 calc R . . C9 C 0.7800(2) 0.15808(11) 0.06456(4) 0.02188(18) Uani 1 1 d . . . C10 C 0.6262(2) 0.10816(13) 0.02377(4) 0.0278(2) Uani 1 1 d . . . H10 H 0.4775 0.1600 0.0171 0.033 Uiso 1 1 calc R . . C11 C 0.6877(3) -0.01692(14) -0.00738(4) 0.0326(2) Uani 1 1 d . . . H11 H 0.5816 -0.0499 -0.0351 0.039 Uiso 1 1 calc R . . C12 C 0.9049(3) -0.09310(13) 0.00232(4) 0.0313(2) Uani 1 1 d . . . H12 H 0.9487 -0.1780 -0.0189 0.038 Uiso 1 1 calc R . . C13 C 1.0576(2) -0.04448(12) 0.04321(4) 0.0279(2) Uani 1 1 d . . . H13 H 1.2047 -0.0975 0.0503 0.033 Uiso 1 1 calc R . . C14 C 0.99667(19) 0.08156(11) 0.07392(4) 0.02332(18) Uani 1 1 d . . . H14 H 1.1039 0.1152 0.1014 0.028 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 O1 0.0481(6) 0.0305(4) 0.0325(4) 0.0034(3) 0.0095(4) -0.0038(4) O2 0.0200(3) 0.0312(3) 0.0242(3) -0.0008(3) 0.0007(3) 0.0000(3) O3 0.0307(4) 0.0373(4) 0.0207(3) -0.0019(3) -0.0013(3) 0.0176(4) O4 0.0302(4) 0.0213(3) 0.0229(3) 0.0025(2) 0.0081(3) 0.0015(3) C1 0.0293(5) 0.0239(4) 0.0198(3) -0.0035(3) 0.0020(4) 0.0016(4) C2 0.0252(5) 0.0255(4) 0.0212(4) -0.0027(3) -0.0045(3) 0.0047(4) C3 0.0186(4) 0.0227(4) 0.0256(4) -0.0006(3) -0.0013(3) 0.0029(4) C4 0.0198(4) 0.0225(4) 0.0232(4) -0.0006(3) 0.0006(3) 0.0049(3) C5 0.0259(5) 0.0373(5) 0.0225(4) 0.0031(4) 0.0009(4) 0.0136(5) C6 0.0213(4) 0.0262(4) 0.0206(3) 0.0020(3) 0.0012(3) 0.0028(4) C7 0.0250(5) 0.0212(4) 0.0230(4) 0.0020(3) 0.0031(4) 0.0025(4) C8 0.0383(6) 0.0221(4) 0.0353(5) 0.0030(4) 0.0175(5) -0.0003(4) C9 0.0228(4) 0.0218(4) 0.0210(3) 0.0049(3) 0.0055(3) -0.0004(3) C10 0.0214(4) 0.0334(5) 0.0286(4) 0.0108(4) -0.0028(4) -0.0003(4) C11 0.0333(6) 0.0407(6) 0.0237(4) 0.0011(4) -0.0062(4) -0.0103(5) C12 0.0358(6) 0.0291(4) 0.0290(4) -0.0057(4) 0.0058(4) -0.0048(5) C13 0.0221(5) 0.0280(4) 0.0334(5) 0.0013(4) 0.0025(4) 0.0024(4) C14 0.0205(4) 0.0276(4) 0.0219(3) 0.0011(3) -0.0013(3) -0.0024(4) _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 1.2061(13) . ? O2 C1 1.3557(13) . ? O2 C4 1.4574(13) . ? O3 C3 1.4389(12) . ? O3 C6 1.4468(12) . ? O4 C7 1.4219(12) . ? O4 C8 1.4359(13) . ? C1 C2 1.5095(17) . ? C2 C3 1.5148(14) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5183(15) . ? C3 H3 1.0000 . ? C4 C5 1.5122(14) . ? C4 H4 1.0000 . ? C5 C6 1.5383(15) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5133(13) . ? C6 H6 1.0000 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5047(15) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.3872(15) . ? C9 C10 1.3934(15) . ? C10 C11 1.3938(17) . ? C10 H10 0.9500 . ? C11 C12 1.390(2) . ? C11 H11 0.9500 . ? C12 C13 1.3881(17) . ? C12 H12 0.9500 . ? C13 C14 1.3936(14) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? 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 C1 O2 C4 110.61(9) . . ? C3 O3 C6 110.28(8) . . ? C7 O4 C8 110.96(7) . . ? O1 C1 O2 121.24(12) . . ? O1 C1 C2 129.21(11) . . ? O2 C1 C2 109.55(9) . . ? C1 C2 C3 102.34(8) . . ? C1 C2 H2A 111.3 . . ? C3 C2 H2A 111.3 . . ? C1 C2 H2B 111.3 . . ? C3 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? O3 C3 C2 109.21(8) . . ? O3 C3 C4 104.68(8) . . ? C2 C3 C4 103.09(8) . . ? O3 C3 H3 113.0 . . ? C2 C3 H3 113.0 . . ? C4 C3 H3 113.0 . . ? O2 C4 C5 110.63(9) . . ? O2 C4 C3 104.26(7) . . ? C5 C4 C3 104.61(8) . . ? O2 C4 H4 112.3 . . ? C5 C4 H4 112.3 . . ? C3 C4 H4 112.3 . . ? C4 C5 C6 103.69(8) . . ? C4 C5 H5A 111.0 . . ? C6 C5 H5A 111.0 . . ? C4 C5 H5B 111.0 . . ? C6 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? O3 C6 C7 110.85(9) . . ? O3 C6 C5 106.80(8) . . ? C7 C6 C5 111.51(8) . . ? O3 C6 H6 109.2 . . ? C7 C6 H6 109.2 . . ? C5 C6 H6 109.2 . . ? O4 C7 C6 109.78(8) . . ? O4 C7 H7A 109.7 . . ? C6 C7 H7A 109.7 . . ? O4 C7 H7B 109.7 . . ? C6 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O4 C8 C9 109.09(8) . . ? O4 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? O4 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C14 C9 C10 119.12(9) . . ? C14 C9 C8 120.93(10) . . ? C10 C9 C8 119.95(11) . . ? C9 C10 C11 120.84(11) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 119.69(11) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 119.63(10) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.51(11) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C9 C14 C13 120.21(10) . . ? C9 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? 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 C4 O2 C1 O1 -177.73(9) . . . . ? C4 O2 C1 C2 2.00(10) . . . . ? O1 C1 C2 C3 158.82(11) . . . . ? O2 C1 C2 C3 -20.89(10) . . . . ? C6 O3 C3 C2 133.49(9) . . . . ? C6 O3 C3 C4 23.67(10) . . . . ? C1 C2 C3 O3 -80.59(10) . . . . ? C1 C2 C3 C4 30.30(9) . . . . ? C1 O2 C4 C5 129.78(9) . . . . ? C1 O2 C4 C3 17.84(10) . . . . ? O3 C3 C4 O2 84.37(9) . . . . ? C2 C3 C4 O2 -29.85(9) . . . . ? O3 C3 C4 C5 -31.86(10) . . . . ? C2 C3 C4 C5 -146.07(9) . . . . ? O2 C4 C5 C6 -84.05(11) . . . . ? C3 C4 C5 C6 27.67(11) . . . . ? C3 O3 C6 C7 115.54(9) . . . . ? C3 O3 C6 C5 -6.11(11) . . . . ? C4 C5 C6 O3 -13.96(12) . . . . ? C4 C5 C6 C7 -135.20(10) . . . . ? C8 O4 C7 C6 -171.59(10) . . . . ? O3 C6 C7 O4 71.57(11) . . . . ? C5 C6 C7 O4 -169.58(9) . . . . ? C7 O4 C8 C9 -165.31(10) . . . . ? O4 C8 C9 C14 -96.54(13) . . . . ? O4 C8 C9 C10 84.49(12) . . . . ? C14 C9 C10 C11 0.02(15) . . . . ? C8 C9 C10 C11 179.01(10) . . . . ? C9 C10 C11 C12 0.08(16) . . . . ? C10 C11 C12 C13 0.48(17) . . . . ? C11 C12 C13 C14 -1.14(17) . . . . ? C10 C9 C14 C13 -0.68(14) . . . . ? C8 C9 C14 C13 -179.66(9) . . . . ? C12 C13 C14 C9 1.25(16) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 32.93 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.320 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.040