data_s07wm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Tricyclic Lactone' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 O3' _chemical_formula_weight 193.21 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.765(2) _cell_length_b 18.967(6) _cell_length_c 7.707(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.286(5) _cell_angle_gamma 90.00 _cell_volume 988.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3617 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 27.84 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.284 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.114 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9008 _diffrn_reflns_av_R_equivalents 0.1031 _diffrn_reflns_av_sigmaI/netI 0.1106 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.83 _reflns_number_total 4508 _reflns_number_gt 3176 _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^)+(0.2000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4(4) _refine_ls_number_reflns 4508 _refine_ls_number_parameters 261 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1871 _refine_ls_R_factor_gt 0.1608 _refine_ls_wR_factor_ref 0.4531 _refine_ls_wR_factor_gt 0.4399 _refine_ls_goodness_of_fit_ref 1.655 _refine_ls_restrained_S_all 1.655 _refine_ls_shift/su_max 2.730 _refine_ls_shift/su_mean 0.100 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 -0.2804(11) 0.4214(3) 0.2909(8) 0.0424(16) Uani 1 1 d . . . O6 O 0.2984(11) 0.3119(3) 0.5489(12) 0.056(2) Uani 1 1 d . . . C6 C -0.0321(15) 0.3524(4) 0.4352(11) 0.0338(19) Uani 1 1 d . . . O2 O 0.4818(12) 0.3762(5) 0.7389(10) 0.066(2) Uani 1 1 d . . . C5 C 0.1910(13) 0.3531(4) 0.4113(15) 0.045(3) Uani 1 1 d . . . C1 C -0.1400(14) 0.3823(4) 0.2799(10) 0.0333(19) Uani 1 1 d . . . C10 C 0.2807(15) 0.4213(4) 0.4886(12) 0.039(2) Uani 1 1 d . . . H10 H 0.372(17) 0.449(6) 0.413(14) 0.047 Uiso 1 1 calc . . . C9 C 0.0949(15) 0.4601(5) 0.5609(10) 0.038(2) Uani 1 1 d . . . H9A H 0.1291 0.4858 0.6689 0.045 Uiso 1 1 calc R . . H9B H 0.0444 0.4945 0.4748 0.045 Uiso 1 1 calc R . . C2 C -0.0640(17) 0.3558(6) 0.1035(11) 0.048(3) Uani 1 1 d . . . H2A H -0.0952 0.3051 0.0898 0.058 Uiso 1 1 calc R . . H2B H -0.1296 0.3820 0.0083 0.058 Uiso 1 1 calc R . . C8 C -0.0557(15) 0.4058(5) 0.5962(10) 0.041(2) Uani 1 1 d . . . H8A H -0.1899 0.4266 0.5989 0.050 Uiso 1 1 calc R . . H8B H -0.0293 0.3817 0.7078 0.050 Uiso 1 1 calc R . . C7 C -0.1251(18) 0.2789(5) 0.472(2) 0.070(4) Uani 1 1 d . . . H7A H -0.1021 0.2477 0.3731 0.105 Uiso 1 1 calc R . . H7B H -0.2677 0.2842 0.4902 0.105 Uiso 1 1 calc R . . H7C H -0.0643 0.2586 0.5764 0.105 Uiso 1 1 calc R . . C4 C 0.2665(17) 0.3289(5) 0.2322(14) 0.052(3) Uani 1 1 d . . . H4A H 0.4092 0.3396 0.2216 0.062 Uiso 1 1 calc R . . H4B H 0.2481 0.2774 0.2193 0.062 Uiso 1 1 calc R . . C11 C 0.3726(16) 0.3739(5) 0.6202(15) 0.050(3) Uani 1 1 d . . . C3 C 0.1541(19) 0.3666(8) 0.0954(14) 0.065(3) Uani 1 1 d . . . H3A H 0.1822 0.4177 0.1051 0.078 Uiso 1 1 calc R . . H3B H 0.2016 0.3507 -0.0194 0.078 Uiso 1 1 calc R . . O3 O 0.7555(10) 0.0600(4) 0.7980(9) 0.0456(17) Uani 1 1 d . . . O5 O 0.1672(12) 0.1779(4) 0.9932(13) 0.065(3) Uani 1 1 d . . . O4 O -0.0058(12) 0.1253(5) 1.2112(10) 0.062(2) Uani 1 1 d . . . C22 C 0.1974(15) 0.0660(4) 0.9797(9) 0.035(2) Uani 1 1 d . . . H22 H 0.107(16) 0.034(6) 0.913(14) 0.042 Uiso 1 1 calc . . . C14 C 0.5474(16) 0.1120(6) 0.5848(12) 0.045(2) Uani 1 1 d . . . H14A H 0.6231 0.0822 0.5032 0.054 Uiso 1 1 calc R . . H14B H 0.5726 0.1620 0.5549 0.054 Uiso 1 1 calc R . . C23 C 0.0975(14) 0.1199(5) 1.0874(12) 0.039(2) Uani 1 1 d . . . C20 C 0.5252(15) 0.0922(5) 1.0828(12) 0.044(2) Uani 1 1 d . . . H20A H 0.4968 0.1217 1.1857 0.053 Uiso 1 1 calc R . . H20B H 0.6630 0.0748 1.0906 0.053 Uiso 1 1 calc R . . C17 C 0.2784(15) 0.1304(4) 0.8762(10) 0.0334(19) Uani 1 1 d . . . C18 C 0.4919(17) 0.1337(5) 0.9154(12) 0.043(2) Uani 1 1 d . . . C13 C 0.6171(14) 0.0981(4) 0.7673(10) 0.0312(18) Uani 1 1 d . . . C21 C 0.3746(16) 0.0290(5) 1.0679(12) 0.042(2) Uani 1 1 d . . . H21A H 0.4274 -0.0096 0.9952 0.050 Uiso 1 1 calc R . . H21B H 0.3390 0.0102 1.1834 0.050 Uiso 1 1 calc R . . C15 C 0.3275(16) 0.0963(6) 0.5650(11) 0.047(2) Uani 1 1 d . . . H15A H 0.2848 0.1060 0.4443 0.057 Uiso 1 1 calc R . . H15B H 0.3024 0.0459 0.5900 0.057 Uiso 1 1 calc R . . C19 C 0.5789(19) 0.2072(6) 0.936(2) 0.074(4) Uani 1 1 d . . . H19A H 0.5043 0.2405 0.8636 0.111 Uiso 1 1 calc R . . H19B H 0.7175 0.2068 0.8994 0.111 Uiso 1 1 calc R . . H19C H 0.5710 0.2217 1.0577 0.111 Uiso 1 1 calc R . . C16 C 0.2125(16) 0.1413(5) 0.6874(13) 0.050(3) Uani 1 1 d . . . H16A H 0.0703 0.1298 0.6764 0.060 Uiso 1 1 calc R . . H16B H 0.2300 0.1914 0.6557 0.060 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 0.047(4) 0.037(3) 0.042(3) 0.004(3) -0.002(3) 0.015(3) O6 0.043(4) 0.033(3) 0.093(6) 0.025(4) -0.028(4) -0.010(3) C6 0.054(5) 0.012(3) 0.036(4) 0.008(3) 0.000(4) 0.001(3) O2 0.050(4) 0.097(7) 0.052(4) 0.029(4) -0.025(4) -0.013(4) C5 0.024(4) 0.024(4) 0.087(7) 0.004(4) -0.028(4) 0.003(3) C1 0.036(5) 0.037(4) 0.027(4) 0.006(3) 0.010(3) -0.009(4) C10 0.046(5) 0.027(4) 0.044(5) 0.008(4) 0.004(4) -0.017(4) C9 0.050(5) 0.049(5) 0.015(3) 0.002(3) -0.005(3) -0.010(4) C2 0.065(7) 0.052(6) 0.028(4) 0.003(4) -0.004(4) 0.018(5) C8 0.053(6) 0.056(5) 0.015(3) 0.014(4) 0.011(3) -0.007(5) C7 0.047(7) 0.025(5) 0.138(13) 0.033(6) -0.002(7) -0.010(4) C4 0.051(6) 0.039(5) 0.066(6) -0.041(5) -0.003(5) 0.017(4) C11 0.045(6) 0.033(5) 0.073(7) 0.027(4) -0.002(5) -0.015(4) C3 0.062(7) 0.091(9) 0.042(5) -0.023(6) 0.005(5) 0.024(7) O3 0.047(4) 0.045(4) 0.045(4) -0.010(3) -0.005(3) 0.016(3) O5 0.050(4) 0.036(4) 0.107(7) -0.035(4) 0.033(4) -0.015(3) O4 0.051(4) 0.080(6) 0.055(4) -0.044(4) 0.016(3) -0.010(4) C22 0.061(6) 0.029(4) 0.014(3) -0.005(3) -0.019(3) -0.004(4) C14 0.049(5) 0.054(6) 0.032(4) 0.005(4) -0.008(4) -0.001(5) C23 0.036(5) 0.042(5) 0.038(4) -0.005(4) -0.009(4) -0.009(4) C20 0.042(5) 0.052(5) 0.038(5) -0.001(4) -0.005(4) -0.015(5) C17 0.061(6) 0.011(3) 0.028(4) 0.005(3) 0.012(4) 0.009(3) C18 0.062(6) 0.029(4) 0.038(5) -0.001(4) 0.015(4) -0.013(4) C13 0.044(5) 0.026(4) 0.024(4) 0.007(3) 0.002(3) 0.004(4) C21 0.046(5) 0.051(5) 0.028(4) 0.018(4) -0.007(4) -0.013(4) C15 0.061(6) 0.056(6) 0.024(4) 0.011(4) -0.001(4) -0.004(5) C19 0.050(7) 0.045(6) 0.127(12) -0.039(7) 0.036(7) -0.022(5) C16 0.047(6) 0.051(6) 0.052(6) 0.027(5) -0.020(5) -0.006(5) _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 1.208(11) . ? O6 C11 1.391(13) . ? O6 C5 1.502(12) . ? C6 C1 1.510(12) . ? C6 C5 1.521(13) . ? C6 C7 1.557(11) . ? C6 C8 1.610(12) . ? O2 C11 1.174(14) . ? C5 C4 1.543(15) . ? C5 C10 1.547(12) . ? C1 C2 1.540(12) . ? C10 C11 1.489(14) . ? C10 C9 1.562(15) . ? C9 C8 1.475(13) . ? C2 C3 1.491(18) . ? C4 C3 1.480(17) . ? O3 C13 1.205(11) . ? O5 C23 1.401(13) . ? O5 C17 1.483(10) . ? O4 C23 1.189(11) . ? C22 C23 1.483(13) . ? C22 C21 1.543(13) . ? C22 C17 1.560(11) . ? C14 C13 1.505(11) . ? C14 C15 1.524(16) . ? C20 C18 1.527(13) . ? C20 C21 1.578(13) . ? C17 C18 1.476(15) . ? C17 C16 1.533(12) . ? C18 C19 1.521(13) . ? C18 C13 1.577(12) . ? C15 C16 1.493(15) . ? 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 C11 O6 C5 90.7(7) . . ? C1 C6 C5 112.1(7) . . ? C1 C6 C7 106.7(9) . . ? C5 C6 C7 115.6(8) . . ? C1 C6 C8 109.0(7) . . ? C5 C6 C8 101.0(8) . . ? C7 C6 C8 112.4(8) . . ? O6 C5 C6 112.8(8) . . ? O6 C5 C4 108.4(8) . . ? C6 C5 C4 116.0(8) . . ? O6 C5 C10 88.6(7) . . ? C6 C5 C10 110.3(8) . . ? C4 C5 C10 117.5(9) . . ? O1 C1 C6 123.5(7) . . ? O1 C1 C2 121.9(8) . . ? C6 C1 C2 114.5(8) . . ? C11 C10 C5 85.4(7) . . ? C11 C10 C9 112.1(8) . . ? C5 C10 C9 102.5(7) . . ? C8 C9 C10 107.1(8) . . ? C3 C2 C1 109.1(9) . . ? C9 C8 C6 103.1(7) . . ? C3 C4 C5 108.8(7) . . ? O2 C11 O6 124.4(9) . . ? O2 C11 C10 140.1(10) . . ? O6 C11 C10 95.3(8) . . ? C2 C3 C4 114.1(11) . . ? C23 O5 C17 90.6(6) . . ? C23 C22 C21 114.9(7) . . ? C23 C22 C17 84.7(6) . . ? C21 C22 C17 107.9(8) . . ? C13 C14 C15 111.1(8) . . ? O4 C23 O5 123.3(9) . . ? O4 C23 C22 141.2(9) . . ? O5 C23 C22 95.5(7) . . ? C18 C20 C21 103.7(7) . . ? C18 C17 O5 110.4(7) . . ? C18 C17 C16 117.9(7) . . ? O5 C17 C16 110.5(8) . . ? C18 C17 C22 105.9(7) . . ? O5 C17 C22 89.1(6) . . ? C16 C17 C22 119.3(8) . . ? C17 C18 C19 116.0(9) . . ? C17 C18 C20 106.9(7) . . ? C19 C18 C20 109.2(10) . . ? C17 C18 C13 111.2(7) . . ? C19 C18 C13 105.0(8) . . ? C20 C18 C13 108.3(8) . . ? O3 C13 C14 121.9(8) . . ? O3 C13 C18 122.3(7) . . ? C14 C13 C18 115.7(8) . . ? C22 C21 C20 100.8(7) . . ? C16 C15 C14 109.7(9) . . ? C15 C16 C17 111.9(8) . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 28.83 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.562 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.138