data_publication_text _publ_requested_journal 'Org.Lett.' _publ_contact_author_name 'Kay M. Brummond' _publ_contact_author_address ;Department of Chemistry University of Pittsburgh Pittsburgh, Pennsylvania 15260 ; _publ_contact_author_email kbrummon@pitt.edu _publ_contact_author_phone 412-624-1955 loop_ _publ_author_name _publ_author_address 'Grillet, Francois' ;Department of Chemistry University of Pittsburgh Pittsburgh, Pennsylvania 15260 ; 'Huang, Chaofeng' ;Department of Chemistry University of Pittsburgh Pittsburgh, Pennsylvania 15260 ; 'Brummond, Kay M.' ;Department of Chemistry University of Pittsburgh Pittsburgh, Pennsylvania 15260 ; data_fgb718s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 O3' _chemical_formula_weight 230.25 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.107(2) _cell_length_b 8.585(2) _cell_length_c 9.637(2) _cell_angle_alpha 112.308(4) _cell_angle_beta 107.086(4) _cell_angle_gamma 97.024(5) _cell_volume 572.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1824 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.62 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9779 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details 'Bruker Sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4915 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2238 _reflns_number_gt 1805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0780P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2238 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.2095 _refine_ls_wR_factor_gt 0.2023 _refine_ls_goodness_of_fit_ref 1.850 _refine_ls_restrained_S_all 1.850 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 0.2776(2) 1.0488(2) 0.0886(2) 0.0719(6) Uani 1 1 d . . . C1 C 0.1708(3) 0.9808(3) -0.0685(3) 0.0582(6) Uani 1 1 d . . . O2 O 0.1128(3) 1.0716(3) -0.1295(2) 0.0834(7) Uani 1 1 d . . . C2 C 0.1449(3) 0.7905(3) -0.1388(3) 0.0610(7) Uani 1 1 d . . . O3 O 0.8776(2) 1.2366(2) 0.5842(2) 0.0776(6) Uani 1 1 d . . . C3 C 0.2739(3) 0.7515(3) -0.0159(3) 0.0559(6) Uani 1 1 d . . . H3A H 0.3868 0.7585 -0.0342 0.067 Uiso 1 1 calc R . . C4 C 0.2194(5) 0.5783(4) -0.0169(4) 0.0856(9) Uani 1 1 d . . . H4A H 0.0943 0.5574 -0.0297 0.103 Uiso 1 1 calc R . . H4B H 0.2267 0.4903 -0.1128 0.103 Uiso 1 1 calc R . . C5 C 0.3150(5) 0.5477(4) 0.1189(4) 0.0927(10) Uani 1 1 d . . . H5A H 0.3270 0.4296 0.0743 0.111 Uiso 1 1 calc R . . H5B H 0.2367 0.5485 0.1782 0.111 Uiso 1 1 calc R . . C6 C 0.4935(3) 0.6594(3) 0.2397(3) 0.0562(6) Uani 1 1 d . . . H6A H 0.5693 0.5999 0.2783 0.067 Uiso 1 1 calc R . . C7 C 0.5633(3) 0.8301(3) 0.3020(3) 0.0477(5) Uani 1 1 d . . . C8 C 0.7449(3) 0.9245(3) 0.4316(3) 0.0555(6) Uani 1 1 d . . . H8A H 0.8381 0.8916 0.3915 0.067 Uiso 1 1 calc R . . H8B H 0.7572 0.8995 0.5237 0.067 Uiso 1 1 calc R . . C9 C 0.7541(3) 1.1135(3) 0.4765(3) 0.0526(6) Uani 1 1 d . . . C10 C 0.5903(3) 1.1257(3) 0.3684(3) 0.0494(6) Uani 1 1 d . . . C11 C 0.4837(3) 0.9626(3) 0.2681(2) 0.0465(5) Uani 1 1 d . . . C12 C 0.3033(3) 0.9106(3) 0.1389(3) 0.0558(6) Uani 1 1 d . . . H12A H 0.2110 0.8878 0.1806 0.067 Uiso 1 1 calc R . . C13 C 0.0222(5) 0.6848(5) -0.2821(4) 0.0864(10) Uani 1 1 d . . . H13A H -0.001(4) 0.541(5) -0.326(4) 0.104(10) Uiso 1 1 d . . . H13B H -0.060(5) 0.728(5) -0.345(4) 0.114(12) Uiso 1 1 d . . . C14 C 0.5646(4) 1.3010(3) 0.3868(3) 0.0629(7) Uani 1 1 d . . . H14B H 0.4521 1.2866 0.3076 0.094 Uiso 1 1 calc R . . H14C H 0.6598 1.3626 0.3717 0.094 Uiso 1 1 calc R . . H14A H 0.5653 1.3664 0.4930 0.094 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 0.0760(12) 0.0526(10) 0.0642(11) 0.0210(8) -0.0022(9) 0.0255(9) C1 0.0488(13) 0.0657(15) 0.0587(14) 0.0320(12) 0.0113(11) 0.0157(11) O2 0.0814(14) 0.0838(14) 0.0837(13) 0.0483(11) 0.0105(11) 0.0293(11) C2 0.0580(14) 0.0658(16) 0.0493(13) 0.0253(11) 0.0107(11) 0.0055(11) O3 0.0649(12) 0.0590(11) 0.0718(12) 0.0175(9) -0.0051(9) 0.0044(9) C3 0.0552(13) 0.0505(13) 0.0488(12) 0.0179(10) 0.0099(10) 0.0061(10) C4 0.084(2) 0.0550(16) 0.0817(19) 0.0277(15) -0.0048(15) -0.0072(14) C5 0.096(2) 0.0543(16) 0.097(2) 0.0386(16) -0.0014(17) -0.0102(15) C6 0.0629(15) 0.0442(12) 0.0629(14) 0.0264(11) 0.0193(11) 0.0190(11) C7 0.0513(12) 0.0445(12) 0.0508(12) 0.0234(10) 0.0180(10) 0.0179(9) C8 0.0526(13) 0.0548(14) 0.0574(13) 0.0273(11) 0.0128(11) 0.0186(10) C9 0.0504(13) 0.0486(13) 0.0506(12) 0.0195(10) 0.0118(10) 0.0106(10) C10 0.0549(13) 0.0405(11) 0.0486(11) 0.0184(9) 0.0151(10) 0.0130(9) C11 0.0478(12) 0.0425(12) 0.0453(12) 0.0178(9) 0.0121(9) 0.0161(9) C12 0.0543(14) 0.0561(14) 0.0536(13) 0.0214(11) 0.0163(11) 0.0210(11) C13 0.085(2) 0.082(2) 0.0627(17) 0.0319(16) -0.0047(15) -0.0001(16) C14 0.0721(16) 0.0407(13) 0.0636(14) 0.0176(11) 0.0145(12) 0.0176(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 O1 C1 1.349(3) . ? O1 C12 1.458(3) . ? C1 O2 1.204(3) . ? C1 C2 1.471(4) . ? C2 C13 1.319(4) . ? C2 C3 1.506(3) . ? O3 C9 1.223(3) . ? C3 C4 1.494(4) . ? C3 C12 1.520(3) . ? C3 H3A 0.9800 . ? C4 C5 1.448(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.481(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.326(3) . ? C6 H6A 0.9300 . ? C7 C11 1.468(3) . ? C7 C8 1.498(3) . ? C8 C9 1.498(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.471(3) . ? C10 C11 1.352(3) . ? C10 C14 1.495(3) . ? C11 C12 1.496(3) . ? C12 H12A 0.9800 . ? C13 H13A 1.12(3) . ? C13 H13B 0.97(4) . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C14 H14A 0.9600 . ? 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 O1 C12 110.56(18) . . ? O2 C1 O1 121.6(2) . . ? O2 C1 C2 130.3(2) . . ? O1 C1 C2 108.2(2) . . ? C13 C2 C1 122.1(3) . . ? C13 C2 C3 130.6(3) . . ? C1 C2 C3 107.2(2) . . ? C2 C3 C4 117.0(2) . . ? C2 C3 C12 100.76(19) . . ? C4 C3 C12 115.9(2) . . ? C2 C3 H3A 107.5 . . ? C4 C3 H3A 107.5 . . ? C12 C3 H3A 107.5 . . ? C5 C4 C3 119.7(2) . . ? C5 C4 H4A 107.4 . . ? C3 C4 H4A 107.4 . . ? C5 C4 H4B 107.4 . . ? C3 C4 H4B 107.4 . . ? H4A C4 H4B 106.9 . . ? C4 C5 C6 123.0(2) . . ? C4 C5 H5A 106.6 . . ? C6 C5 H5A 106.6 . . ? C4 C5 H5B 106.6 . . ? C6 C5 H5B 106.6 . . ? H5A C5 H5B 106.5 . . ? C7 C6 C5 130.8(2) . . ? C7 C6 H6A 114.6 . . ? C5 C6 H6A 114.6 . . ? C6 C7 C11 129.3(2) . . ? C6 C7 C8 123.8(2) . . ? C11 C7 C8 106.89(18) . . ? C7 C8 C9 104.13(18) . . ? C7 C8 H8A 110.9 . . ? C9 C8 H8A 110.9 . . ? C7 C8 H8B 110.9 . . ? C9 C8 H8B 110.9 . . ? H8A C8 H8B 108.9 . . ? O3 C9 C10 125.8(2) . . ? O3 C9 C8 125.7(2) . . ? C10 C9 C8 108.51(19) . . ? C11 C10 C9 108.6(2) . . ? C11 C10 C14 131.7(2) . . ? C9 C10 C14 119.7(2) . . ? C10 C11 C7 111.66(19) . . ? C10 C11 C12 127.7(2) . . ? C7 C11 C12 120.59(19) . . ? O1 C12 C11 110.77(19) . . ? O1 C12 C3 104.47(18) . . ? C11 C12 C3 114.17(19) . . ? O1 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C3 C12 H12A 109.1 . . ? C2 C13 H13A 119.6(16) . . ? C2 C13 H13B 122(2) . . ? H13A C13 H13B 118(3) . . ? C10 C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C14 H14A 109.5 . . ? H14B C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.341 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.079