# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1621 data_ohj9m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H24 O3' _chemical_formula_weight 276.36 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)/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 9.8448(9) _cell_length_b 13.2382(12) _cell_length_c 11.0507(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.152(2) _cell_angle_gamma 90.00 _cell_volume 1421.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 '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 9135 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3388 _reflns_number_gt 2566 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1134P)^2^+0.2349P] 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 3388 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1820 _refine_ls_wR_factor_gt 0.1677 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.16180(12) 0.12485(9) 0.90139(11) 0.0243(3) Uani 1 1 d . . . O2 O 0.17633(12) 0.18209(9) 0.70525(10) 0.0233(3) Uani 1 1 d . . . O3 O 0.02657(13) 0.06533(10) 0.73876(12) 0.0307(3) Uani 1 1 d . . . C1 C 0.26935(16) 0.28767(13) 0.87837(14) 0.0211(3) Uani 1 1 d . . . C2 C 0.12751(18) 0.34215(14) 0.87229(16) 0.0251(4) Uani 1 1 d . . . H2A H 0.0799 0.3474 0.7866 0.030 Uiso 1 1 calc R . . H2B H 0.0675 0.3054 0.9212 0.030 Uiso 1 1 calc R . . C3 C 0.1636(2) 0.44486(14) 0.92528(17) 0.0317(4) Uani 1 1 d . . . H3A H 0.0973 0.4952 0.9349 0.038 Uiso 1 1 calc R . . C4 C 0.2980(2) 0.45773(15) 0.95726(17) 0.0324(4) Uani 1 1 d . . . H4A H 0.3383 0.5185 0.9920 0.039 Uiso 1 1 calc R . . C5 C 0.37963(18) 0.36697(13) 0.93307(16) 0.0257(4) Uani 1 1 d . . . H5A H 0.4347 0.3416 1.0099 0.031 Uiso 1 1 calc R . . H5B H 0.4423 0.3829 0.8740 0.031 Uiso 1 1 calc R . . C6 C 0.27428(17) 0.19177(13) 0.95850(15) 0.0227(4) Uani 1 1 d . . . C7 C 0.40801(18) 0.13249(14) 0.96443(16) 0.0270(4) Uani 1 1 d . . . H7A H 0.4851 0.1742 1.0059 0.032 Uiso 1 1 calc R . . H7B H 0.4027 0.0709 1.0142 0.032 Uiso 1 1 calc R . . C8 C 0.43765(18) 0.10221(14) 0.83857(16) 0.0278(4) Uani 1 1 d . . . H8A H 0.3715 0.0495 0.8036 0.033 Uiso 1 1 calc R . . H8B H 0.5315 0.0734 0.8465 0.033 Uiso 1 1 calc R . . C9 C 0.42630(17) 0.19290(13) 0.75234(16) 0.0244(4) Uani 1 1 d . . . H9A H 0.4324 0.1692 0.6684 0.029 Uiso 1 1 calc R . . H9B H 0.5047 0.2390 0.7784 0.029 Uiso 1 1 calc R . . C10 C 0.29135(16) 0.25142(12) 0.75026(15) 0.0209(3) Uani 1 1 d . . . C11 C 0.27891(18) 0.33506(13) 0.65318(15) 0.0242(4) Uani 1 1 d . . . H11A H 0.1934 0.3736 0.6565 0.029 Uiso 1 1 calc R . . H11B H 0.3573 0.3822 0.6739 0.029 Uiso 1 1 calc R . . C12 C 0.27664(19) 0.29742(14) 0.52404(16) 0.0276(4) Uani 1 1 d . . . H12A H 0.2298 0.2359 0.5011 0.033 Uiso 1 1 calc R . . C13 C 0.2432(2) 0.21217(14) 1.08902(16) 0.0280(4) Uani 1 1 d . . . H13A H 0.3265 0.2409 1.1392 0.034 Uiso 1 1 calc R . . H13B H 0.1695 0.2636 1.0840 0.034 Uiso 1 1 calc R . . C14 C 0.1996(2) 0.12054(14) 1.15286(17) 0.0293(4) Uani 1 1 d . . . H14A H 0.1205 0.0856 1.1133 0.035 Uiso 1 1 calc R . . C15 C 0.2598(2) 0.08404(18) 1.25767(19) 0.0380(5) Uani 1 1 d . . . H15A H 0.2101 0.0239 1.2783 0.057 Uiso 1 1 calc R . . H15B H 0.2595 0.1351 1.3219 0.057 Uiso 1 1 calc R . . H15C H 0.3549 0.0657 1.2515 0.057 Uiso 1 1 calc R . . C16 C 0.3357(2) 0.34458(18) 0.44100(18) 0.0373(5) Uani 1 1 d . . . H16A H 0.3207 0.3061 0.3643 0.056 Uiso 1 1 calc R . . H16B H 0.4347 0.3506 0.4704 0.056 Uiso 1 1 calc R . . H16C H 0.2955 0.4121 0.4266 0.056 Uiso 1 1 calc R . . C17 C 0.11863(17) 0.12175(13) 0.77966(16) 0.0232(4) Uani 1 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 0.0252(6) 0.0232(6) 0.0240(6) 0.0001(4) 0.0020(5) -0.0051(5) O2 0.0237(6) 0.0231(6) 0.0222(6) -0.0014(4) 0.0002(4) -0.0042(5) O3 0.0291(7) 0.0312(7) 0.0315(7) -0.0056(5) 0.0040(5) -0.0102(6) C1 0.0210(8) 0.0197(8) 0.0214(8) -0.0002(6) -0.0001(6) -0.0011(6) C2 0.0252(8) 0.0243(9) 0.0258(8) 0.0003(6) 0.0039(6) 0.0032(7) C3 0.0429(11) 0.0210(9) 0.0338(10) -0.0001(7) 0.0138(8) 0.0047(8) C4 0.0459(11) 0.0234(9) 0.0289(9) -0.0058(7) 0.0091(8) -0.0073(8) C5 0.0288(9) 0.0243(9) 0.0226(8) -0.0021(6) 0.0000(6) -0.0064(7) C6 0.0225(8) 0.0221(8) 0.0223(8) 0.0002(6) -0.0001(6) -0.0031(6) C7 0.0258(8) 0.0264(9) 0.0276(9) 0.0059(7) 0.0007(6) 0.0031(7) C8 0.0261(9) 0.0255(9) 0.0319(9) 0.0050(7) 0.0050(7) 0.0061(7) C9 0.0229(8) 0.0238(9) 0.0265(8) 0.0014(6) 0.0042(6) 0.0026(7) C10 0.0203(8) 0.0186(8) 0.0227(8) -0.0003(6) 0.0000(6) -0.0011(6) C11 0.0269(8) 0.0206(8) 0.0243(8) 0.0019(6) 0.0017(6) -0.0005(6) C12 0.0286(9) 0.0279(9) 0.0254(9) 0.0019(7) 0.0015(7) 0.0018(7) C13 0.0342(9) 0.0272(9) 0.0223(8) 0.0002(6) 0.0033(7) -0.0028(7) C14 0.0308(9) 0.0320(10) 0.0251(9) -0.0004(7) 0.0041(7) -0.0067(7) C15 0.0349(10) 0.0451(12) 0.0338(10) 0.0099(9) 0.0044(8) -0.0057(9) C16 0.0350(10) 0.0457(12) 0.0313(10) 0.0089(9) 0.0060(8) 0.0066(9) C17 0.0228(8) 0.0217(8) 0.0252(8) -0.0019(6) 0.0043(6) -0.0007(6) _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 C17 1.345(2) . ? O1 C6 1.4789(19) . ? O2 C17 1.336(2) . ? O2 C10 1.4807(19) . ? O3 C17 1.205(2) . ? C1 C10 1.542(2) . ? C1 C6 1.544(2) . ? C1 C5 1.561(2) . ? C1 C2 1.564(2) . ? C2 C3 1.501(3) . ? C3 C4 1.325(3) . ? C4 C5 1.493(3) . ? C6 C7 1.525(2) . ? C6 C13 1.545(2) . ? C7 C8 1.520(3) . ? C8 C9 1.526(2) . ? C9 C10 1.535(2) . ? C10 C11 1.533(2) . ? C11 C12 1.508(2) . ? C12 C16 1.319(3) . ? C13 C14 1.500(3) . ? C14 C15 1.307(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 C17 O1 C6 122.75(13) . . ? C17 O2 C10 122.76(12) . . ? C10 C1 C6 105.92(13) . . ? C10 C1 C5 111.97(13) . . ? C6 C1 C5 111.98(13) . . ? C10 C1 C2 111.03(13) . . ? C6 C1 C2 110.50(14) . . ? C5 C1 C2 105.53(13) . . ? C3 C2 C1 104.30(14) . . ? C4 C3 C2 112.63(17) . . ? C3 C4 C5 113.07(17) . . ? C4 C5 C1 104.45(14) . . ? O1 C6 C7 107.02(14) . . ? O1 C6 C1 107.13(12) . . ? C7 C6 C1 113.32(14) . . ? O1 C6 C13 104.89(13) . . ? C7 C6 C13 110.35(14) . . ? C1 C6 C13 113.50(15) . . ? C8 C7 C6 112.74(14) . . ? C7 C8 C9 111.00(15) . . ? C8 C9 C10 112.57(14) . . ? O2 C10 C11 103.94(12) . . ? O2 C10 C9 107.82(13) . . ? C11 C10 C9 110.34(14) . . ? O2 C10 C1 106.84(13) . . ? C11 C10 C1 114.22(14) . . ? C9 C10 C1 113.01(13) . . ? C12 C11 C10 114.27(14) . . ? C16 C12 C11 124.06(19) . . ? C14 C13 C6 114.31(15) . . ? C15 C14 C13 126.34(18) . . ? O3 C17 O2 120.50(15) . . ? O3 C17 O1 119.53(15) . . ? O2 C17 O1 119.96(14) . . ? 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 C10 C1 C2 C3 -122.99(15) . . . . ? C6 C1 C2 C3 119.78(15) . . . . ? C5 C1 C2 C3 -1.47(17) . . . . ? C1 C2 C3 C4 1.1(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C1 -0.8(2) . . . . ? C10 C1 C5 C4 122.28(15) . . . . ? C6 C1 C5 C4 -118.92(15) . . . . ? C2 C1 C5 C4 1.36(17) . . . . ? C17 O1 C6 C7 -90.15(18) . . . . ? C17 O1 C6 C1 31.7(2) . . . . ? C17 O1 C6 C13 152.61(15) . . . . ? C10 C1 C6 O1 -60.39(16) . . . . ? C5 C1 C6 O1 177.29(13) . . . . ? C2 C1 C6 O1 59.95(17) . . . . ? C10 C1 C6 C7 57.42(17) . . . . ? C5 C1 C6 C7 -64.90(19) . . . . ? C2 C1 C6 C7 177.76(14) . . . . ? C10 C1 C6 C13 -175.69(13) . . . . ? C5 C1 C6 C13 61.99(18) . . . . ? C2 C1 C6 C13 -55.35(18) . . . . ? O1 C6 C7 C8 61.41(18) . . . . ? C1 C6 C7 C8 -56.5(2) . . . . ? C13 C6 C7 C8 175.00(15) . . . . ? C6 C7 C8 C9 50.5(2) . . . . ? C7 C8 C9 C10 -50.48(19) . . . . ? C17 O2 C10 C11 -154.65(14) . . . . ? C17 O2 C10 C9 88.22(17) . . . . ? C17 O2 C10 C1 -33.53(19) . . . . ? C8 C9 C10 O2 -61.52(18) . . . . ? C8 C9 C10 C11 -174.41(14) . . . . ? C8 C9 C10 C1 56.33(19) . . . . ? C6 C1 C10 O2 61.18(15) . . . . ? C5 C1 C10 O2 -176.49(12) . . . . ? C2 C1 C10 O2 -58.82(17) . . . . ? C6 C1 C10 C11 175.51(13) . . . . ? C5 C1 C10 C11 -62.16(18) . . . . ? C2 C1 C10 C11 55.52(18) . . . . ? C6 C1 C10 C9 -57.24(17) . . . . ? C5 C1 C10 C9 65.08(18) . . . . ? C2 C1 C10 C9 -177.24(14) . . . . ? O2 C10 C11 C12 -54.25(18) . . . . ? C9 C10 C11 C12 61.12(18) . . . . ? C1 C10 C11 C12 -170.28(14) . . . . ? C10 C11 C12 C16 -143.06(19) . . . . ? O1 C6 C13 C14 43.36(19) . . . . ? C7 C6 C13 C14 -71.58(19) . . . . ? C1 C6 C13 C14 159.98(15) . . . . ? C6 C13 C14 C15 122.0(2) . . . . ? C10 O2 C17 O3 -178.83(15) . . . . ? C10 O2 C17 O1 2.2(2) . . . . ? C6 O1 C17 O3 179.83(15) . . . . ? C6 O1 C17 O2 -1.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.505 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.080 data_ohj8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 O2' _chemical_formula_weight 220.30 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 P2(1)/c 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 16.567(6) _cell_length_b 13.585(5) _cell_length_c 13.245(4) _cell_angle_alpha 90.00 _cell_angle_beta 128.712(5) _cell_angle_gamma 90.00 _cell_volume 2326.2(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9790 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13543 _diffrn_reflns_av_R_equivalents 0.1486 _diffrn_reflns_av_sigmaI/netI 0.1632 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.33 _reflns_number_total 5463 _reflns_number_gt 2514 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0774P)^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 SHELXL _refine_ls_extinction_coef 0.027(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5463 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1894 _refine_ls_R_factor_gt 0.0852 _refine_ls_wR_factor_ref 0.1995 _refine_ls_wR_factor_gt 0.1551 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 O1A O 0.28039(16) 0.42423(17) 0.4927(2) 0.0416(6) Uani 1 1 d . . . H1AA H 0.2502 0.3722 0.4799 0.062 Uiso 1 1 calc R . . O2A O 0.5218(2) 0.4106(2) 0.9615(2) 0.0562(8) Uani 1 1 d . . . H2AA H 0.5084 0.4655 0.9732 0.084 Uiso 1 1 calc R . . C1A C 0.4020(2) 0.3968(2) 0.7267(3) 0.0280(7) Uani 1 1 d . . . C2A C 0.3636(3) 0.2943(3) 0.7317(4) 0.0494(11) Uani 1 1 d . . . H2AB H 0.3316 0.2589 0.6512 0.059 Uiso 1 1 calc R . . H2AC H 0.4205 0.2553 0.8023 0.059 Uiso 1 1 calc R . . C3A C 0.2864(3) 0.3156(5) 0.7525(4) 0.0773(18) Uani 1 1 d . . . H3AA H 0.2533 0.2673 0.7645 0.093 Uiso 1 1 calc R . . C4A C 0.2707(3) 0.4111(5) 0.7519(5) 0.0800(18) Uani 1 1 d . . . H4AA H 0.2252 0.4373 0.7636 0.096 Uiso 1 1 calc R . . C5A C 0.3316(3) 0.4710(3) 0.7312(4) 0.0504(11) Uani 1 1 d . . . H5AA H 0.3735 0.5177 0.8013 0.061 Uiso 1 1 calc R . . H5AB H 0.2870 0.5070 0.6504 0.061 Uiso 1 1 calc R . . C6A C 0.3886(2) 0.4130(2) 0.6004(3) 0.0276(7) Uani 1 1 d . . . C7A C 0.4261(3) 0.3286(3) 0.5638(3) 0.0429(9) Uani 1 1 d . . . H7A1 H 0.3790 0.2741 0.5383 0.051 Uiso 1 1 calc R . . H7A2 H 0.4165 0.3491 0.4868 0.051 Uiso 1 1 calc R . . C8A C 0.5334(3) 0.2877(3) 0.6553(4) 0.0529(11) Uani 1 1 d . . . H8AA H 0.5571 0.2568 0.6156 0.064 Uiso 1 1 calc R . . C9A C 0.5998(3) 0.2884(3) 0.7829(4) 0.0457(10) Uani 1 1 d . . . H9AA H 0.6624 0.2575 0.8179 0.055 Uiso 1 1 calc R . . C10A C 0.5922(2) 0.3294(3) 0.8802(3) 0.0351(8) Uani 1 1 d . . . H10A H 0.6608 0.3526 0.9516 0.042 Uiso 1 1 calc R . . H10B H 0.5771 0.2746 0.9129 0.042 Uiso 1 1 calc R . . C11A C 0.5164(2) 0.4123(2) 0.8490(3) 0.0314(7) Uani 1 1 d . . . C12A C 0.5556(3) 0.5113(3) 0.8444(4) 0.0496(11) Uani 1 1 d . . . H12A H 0.5164 0.5628 0.8471 0.059 Uiso 1 1 calc R . . H12B H 0.6274 0.5184 0.9204 0.059 Uiso 1 1 calc R . . C13A C 0.5470(3) 0.5246(3) 0.7251(4) 0.0563(12) Uani 1 1 d . . . H13A H 0.5905 0.4769 0.7251 0.068 Uiso 1 1 calc R . . H13B H 0.5705 0.5900 0.7250 0.068 Uiso 1 1 calc R . . C14A C 0.4345(3) 0.5109(3) 0.6040(3) 0.0388(8) Uani 1 1 d . . . H14A H 0.3931 0.5637 0.5999 0.047 Uiso 1 1 calc R . . H14B H 0.4308 0.5160 0.5282 0.047 Uiso 1 1 calc R . . O1B O -0.15583(17) 0.75616(19) 0.0749(2) 0.0471(7) Uani 1 1 d . . . H1BA H -0.1767 0.8123 0.0688 0.071 Uiso 1 1 calc R . . O2B O 0.12764(16) 0.53177(16) 0.2754(2) 0.0364(6) Uani 1 1 d . . . H2BA H 0.1758 0.5135 0.3488 0.055 Uiso 1 1 calc R . . C1B C -0.0071(2) 0.6499(2) 0.1627(3) 0.0234(6) Uani 1 1 d . . . C2B C -0.0334(2) 0.6258(2) 0.0312(3) 0.0300(7) Uani 1 1 d . . . H2BB H -0.0458 0.6856 -0.0166 0.036 Uiso 1 1 calc R . . H2BC H 0.0227 0.5898 0.0434 0.036 Uiso 1 1 calc R . . C3B C -0.1292(3) 0.5641(3) -0.0393(4) 0.0453(10) Uani 1 1 d . . . H3BA H -0.1693 0.5480 -0.1266 0.054 Uiso 1 1 calc R . . C4B C -0.1494(3) 0.5359(3) 0.0357(5) 0.0514(11) Uani 1 1 d . . . H4BA H -0.2052 0.4958 0.0088 0.062 Uiso 1 1 calc R . . C5B C -0.0739(3) 0.5745(3) 0.1705(4) 0.0437(9) Uani 1 1 d . . . H5BA H -0.0313 0.5218 0.2305 0.052 Uiso 1 1 calc R . . H5BB H -0.1094 0.6065 0.1983 0.052 Uiso 1 1 calc R . . C6B C -0.0428(2) 0.7556(2) 0.1644(3) 0.0294(7) Uani 1 1 d . . . C7B C -0.0130(3) 0.8374(2) 0.1146(3) 0.0406(9) Uani 1 1 d . . . H7B1 H -0.0503 0.8255 0.0231 0.049 Uiso 1 1 calc R . . H7B2 H -0.0396 0.8985 0.1216 0.049 Uiso 1 1 calc R . . C8B C 0.0973(3) 0.8550(3) 0.1734(4) 0.0486(10) Uani 1 1 d . . . H8BA H 0.1122 0.9190 0.1649 0.058 Uiso 1 1 calc R . . C9B C 0.1780(3) 0.7941(3) 0.2360(4) 0.0468(10) Uani 1 1 d . . . H9BA H 0.2407 0.8234 0.2683 0.056 Uiso 1 1 calc R . . C10B C 0.1843(2) 0.6870(3) 0.2629(3) 0.0349(8) Uani 1 1 d . . . H10C H 0.2537 0.6747 0.3420 0.042 Uiso 1 1 calc R . . H10D H 0.1788 0.6534 0.1942 0.042 Uiso 1 1 calc R . . C11B C 0.1097(2) 0.6343(2) 0.2773(3) 0.0256(7) Uani 1 1 d . . . C12B C 0.1327(2) 0.6607(3) 0.4041(3) 0.0333(8) Uani 1 1 d . . . H12C H 0.2063 0.6528 0.4736 0.040 Uiso 1 1 calc R . . H12D H 0.0966 0.6150 0.4196 0.040 Uiso 1 1 calc R . . C13B C 0.1016(3) 0.7652(3) 0.4078(3) 0.0368(8) Uani 1 1 d . . . H13C H 0.1427 0.8118 0.4018 0.044 Uiso 1 1 calc R . . H13D H 0.1145 0.7762 0.4891 0.044 Uiso 1 1 calc R . . C14B C -0.0132(3) 0.7811(3) 0.2953(3) 0.0353(8) Uani 1 1 d . . . H14C H -0.0539 0.7412 0.3093 0.042 Uiso 1 1 calc R . . H14D H -0.0303 0.8496 0.2944 0.042 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 O1A 0.0284(12) 0.0351(13) 0.0306(13) 0.0100(10) 0.0034(10) -0.0055(9) O2A 0.0749(19) 0.0551(17) 0.0295(14) -0.0001(12) 0.0283(14) 0.0219(14) C1A 0.0230(15) 0.0313(18) 0.0293(17) 0.0072(13) 0.0161(14) 0.0053(12) C2A 0.0305(18) 0.051(2) 0.045(2) 0.0264(18) 0.0129(17) -0.0024(16) C3A 0.030(2) 0.144(5) 0.047(3) 0.042(3) 0.019(2) -0.010(3) C4A 0.042(2) 0.153(6) 0.057(3) 0.046(3) 0.037(2) 0.037(3) C5A 0.044(2) 0.069(3) 0.044(2) 0.022(2) 0.0307(19) 0.0310(19) C6A 0.0226(15) 0.0293(17) 0.0230(16) 0.0033(13) 0.0105(13) -0.0006(12) C7A 0.058(2) 0.042(2) 0.0308(19) -0.0031(16) 0.0285(18) 0.0033(17) C8A 0.067(3) 0.061(3) 0.050(3) 0.0096(19) 0.046(2) 0.027(2) C9A 0.037(2) 0.052(2) 0.056(3) 0.0116(18) 0.033(2) 0.0167(16) C10A 0.0232(15) 0.0372(19) 0.0292(17) 0.0009(14) 0.0087(14) 0.0057(13) C11A 0.0323(16) 0.0335(18) 0.0237(16) -0.0053(14) 0.0153(14) 0.0067(13) C12A 0.0340(19) 0.037(2) 0.038(2) -0.0058(16) 0.0029(17) -0.0050(15) C13A 0.035(2) 0.041(2) 0.071(3) 0.011(2) 0.022(2) -0.0127(16) C14A 0.0362(18) 0.035(2) 0.041(2) 0.0069(15) 0.0219(17) -0.0049(14) O1B 0.0282(12) 0.0505(15) 0.0427(15) -0.0041(12) 0.0125(11) 0.0199(10) O2B 0.0380(13) 0.0319(13) 0.0263(12) 0.0056(10) 0.0138(11) 0.0141(10) C1B 0.0245(14) 0.0263(16) 0.0237(16) 0.0053(12) 0.0171(13) 0.0050(12) C2B 0.0288(16) 0.0314(17) 0.0248(16) -0.0014(13) 0.0143(14) 0.0063(12) C3B 0.0297(18) 0.041(2) 0.044(2) -0.0146(17) 0.0126(17) 0.0037(14) C4B 0.0306(19) 0.035(2) 0.078(3) -0.011(2) 0.029(2) -0.0071(15) C5B 0.0386(19) 0.040(2) 0.064(3) 0.0101(18) 0.038(2) 0.0002(15) C6B 0.0248(15) 0.0354(18) 0.0238(16) 0.0005(13) 0.0131(14) 0.0099(13) C7B 0.060(2) 0.0274(18) 0.0285(18) 0.0008(14) 0.0249(18) 0.0058(16) C8B 0.088(3) 0.031(2) 0.065(3) -0.0026(18) 0.066(3) -0.0098(19) C9B 0.061(2) 0.044(2) 0.068(3) -0.022(2) 0.056(2) -0.0211(19) C10B 0.0240(16) 0.049(2) 0.0329(18) -0.0068(15) 0.0185(15) -0.0013(14) C11B 0.0263(15) 0.0280(17) 0.0228(16) 0.0038(12) 0.0156(14) 0.0073(12) C12B 0.0340(17) 0.044(2) 0.0215(16) 0.0060(14) 0.0171(15) 0.0110(14) C13B 0.0403(19) 0.049(2) 0.0247(18) -0.0006(15) 0.0219(16) 0.0107(15) C14B 0.0401(18) 0.043(2) 0.0313(18) 0.0011(15) 0.0264(16) 0.0125(15) _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 O1A C6A 1.440(4) . ? O2A C11A 1.435(4) . ? C1A C2A 1.549(5) . ? C1A C11A 1.556(4) . ? C1A C6A 1.559(5) . ? C1A C5A 1.572(5) . ? C2A C3A 1.496(7) . ? C3A C4A 1.322(8) . ? C4A C5A 1.449(7) . ? C6A C14A 1.518(4) . ? C6A C7A 1.519(5) . ? C7A C8A 1.498(5) . ? C8A C9A 1.320(6) . ? C9A C10A 1.479(5) . ? C10A C11A 1.538(4) . ? C11A C12A 1.511(5) . ? C12A C13A 1.506(6) . ? C13A C14A 1.530(5) . ? O1B C6B 1.461(4) . ? O2B C11B 1.428(4) . ? C1B C2B 1.543(4) . ? C1B C11B 1.555(4) . ? C1B C6B 1.558(4) . ? C1B C5B 1.559(4) . ? C2B C3B 1.497(5) . ? C3B C4B 1.289(6) . ? C4B C5B 1.495(6) . ? C6B C14B 1.517(5) . ? C6B C7B 1.524(5) . ? C7B C8B 1.492(5) . ? C8B C9B 1.331(6) . ? C9B C10B 1.486(5) . ? C10B C11B 1.541(4) . ? C11B C12B 1.514(4) . ? C12B C13B 1.522(5) . ? C13B C14B 1.529(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 C2A C1A C11A 110.0(3) . . ? C2A C1A C6A 112.7(3) . . ? C11A C1A C6A 111.2(2) . . ? C2A C1A C5A 103.9(3) . . ? C11A C1A C5A 108.8(3) . . ? C6A C1A C5A 109.8(3) . . ? C3A C2A C1A 104.8(4) . . ? C4A C3A C2A 112.1(4) . . ? C3A C4A C5A 113.3(4) . . ? C4A C5A C1A 105.5(4) . . ? O1A C6A C14A 103.1(2) . . ? O1A C6A C7A 105.6(3) . . ? C14A C6A C7A 112.0(3) . . ? O1A C6A C1A 109.4(2) . . ? C14A C6A C1A 110.9(3) . . ? C7A C6A C1A 115.0(3) . . ? C8A C7A C6A 122.5(3) . . ? C9A C8A C7A 130.6(3) . . ? C8A C9A C10A 131.4(3) . . ? C9A C10A C11A 122.8(3) . . ? O2A C11A C12A 107.8(3) . . ? O2A C11A C10A 101.5(3) . . ? C12A C11A C10A 111.3(3) . . ? O2A C11A C1A 108.9(3) . . ? C12A C11A C1A 110.7(3) . . ? C10A C11A C1A 116.0(3) . . ? C13A C12A C11A 112.8(3) . . ? C12A C13A C14A 109.8(3) . . ? C6A C14A C13A 113.4(3) . . ? C2B C1B C11B 112.0(2) . . ? C2B C1B C6B 111.8(2) . . ? C11B C1B C6B 111.3(2) . . ? C2B C1B C5B 103.0(3) . . ? C11B C1B C5B 110.3(2) . . ? C6B C1B C5B 108.2(2) . . ? C3B C2B C1B 105.3(3) . . ? C4B C3B C2B 111.8(3) . . ? C3B C4B C5B 112.9(3) . . ? C4B C5B C1B 104.5(3) . . ? O1B C6B C14B 105.1(2) . . ? O1B C6B C7B 104.0(2) . . ? C14B C6B C7B 111.5(3) . . ? O1B C6B C1B 107.4(2) . . ? C14B C6B C1B 111.9(3) . . ? C7B C6B C1B 115.9(3) . . ? C8B C7B C6B 120.9(3) . . ? C9B C8B C7B 130.6(3) . . ? C8B C9B C10B 130.6(3) . . ? C9B C10B C11B 122.9(3) . . ? O2B C11B C12B 109.9(2) . . ? O2B C11B C10B 105.0(2) . . ? C12B C11B C10B 111.2(3) . . ? O2B C11B C1B 105.2(2) . . ? C12B C11B C1B 110.4(2) . . ? C10B C11B C1B 114.8(2) . . ? C11B C12B C13B 113.6(3) . . ? C12B C13B C14B 109.9(3) . . ? C6B C14B C13B 113.5(3) . . ? 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 C11A C1A C2A C3A 110.6(3) . . . . ? C6A C1A C2A C3A -124.7(3) . . . . ? C5A C1A C2A C3A -5.8(4) . . . . ? C1A C2A C3A C4A 3.9(5) . . . . ? C2A C3A C4A C5A 0.1(6) . . . . ? C3A C4A C5A C1A -4.0(5) . . . . ? C2A C1A C5A C4A 5.9(4) . . . . ? C11A C1A C5A C4A -111.3(4) . . . . ? C6A C1A C5A C4A 126.7(3) . . . . ? C2A C1A C6A O1A 71.2(3) . . . . ? C11A C1A C6A O1A -164.7(2) . . . . ? C5A C1A C6A O1A -44.1(3) . . . . ? C2A C1A C6A C14A -175.7(3) . . . . ? C11A C1A C6A C14A -51.6(3) . . . . ? C5A C1A C6A C14A 68.9(3) . . . . ? C2A C1A C6A C7A -47.3(4) . . . . ? C11A C1A C6A C7A 76.8(3) . . . . ? C5A C1A C6A C7A -162.7(3) . . . . ? O1A C6A C7A C8A -174.8(3) . . . . ? C14A C6A C7A C8A 73.7(4) . . . . ? C1A C6A C7A C8A -54.2(4) . . . . ? C6A C7A C8A C9A 24.6(7) . . . . ? C7A C8A C9A C10A -0.2(8) . . . . ? C8A C9A C10A C11A -22.2(7) . . . . ? C9A C10A C11A O2A 167.9(3) . . . . ? C9A C10A C11A C12A -77.6(4) . . . . ? C9A C10A C11A C1A 50.1(5) . . . . ? C2A C1A C11A O2A -62.6(3) . . . . ? C6A C1A C11A O2A 171.8(3) . . . . ? C5A C1A C11A O2A 50.7(3) . . . . ? C2A C1A C11A C12A 179.0(3) . . . . ? C6A C1A C11A C12A 53.4(4) . . . . ? C5A C1A C11A C12A -67.7(4) . . . . ? C2A C1A C11A C10A 51.0(4) . . . . ? C6A C1A C11A C10A -74.6(3) . . . . ? C5A C1A C11A C10A 164.3(3) . . . . ? O2A C11A C12A C13A -176.2(3) . . . . ? C10A C11A C12A C13A 73.4(4) . . . . ? C1A C11A C12A C13A -57.2(4) . . . . ? C11A C12A C13A C14A 57.2(4) . . . . ? O1A C6A C14A C13A 170.3(3) . . . . ? C7A C6A C14A C13A -76.7(4) . . . . ? C1A C6A C14A C13A 53.3(4) . . . . ? C12A C13A C14A C6A -55.4(4) . . . . ? C11B C1B C2B C3B 133.9(3) . . . . ? C6B C1B C2B C3B -100.5(3) . . . . ? C5B C1B C2B C3B 15.4(3) . . . . ? C1B C2B C3B C4B -11.3(4) . . . . ? C2B C3B C4B C5B 1.5(4) . . . . ? C3B C4B C5B C1B 8.8(4) . . . . ? C2B C1B C5B C4B -14.5(3) . . . . ? C11B C1B C5B C4B -134.2(3) . . . . ? C6B C1B C5B C4B 103.9(3) . . . . ? C2B C1B C6B O1B 67.5(3) . . . . ? C11B C1B C6B O1B -166.5(2) . . . . ? C5B C1B C6B O1B -45.2(3) . . . . ? C2B C1B C6B C14B -177.6(3) . . . . ? C11B C1B C6B C14B -51.6(3) . . . . ? C5B C1B C6B C14B 69.7(3) . . . . ? C2B C1B C6B C7B -48.3(3) . . . . ? C11B C1B C6B C7B 77.8(3) . . . . ? C5B C1B C6B C7B -161.0(3) . . . . ? O1B C6B C7B C8B -174.5(3) . . . . ? C14B C6B C7B C8B 72.7(4) . . . . ? C1B C6B C7B C8B -56.8(4) . . . . ? C6B C7B C8B C9B 25.7(6) . . . . ? C7B C8B C9B C10B 3.4(7) . . . . ? C8B C9B C10B C11B -29.0(6) . . . . ? C9B C10B C11B O2B 168.5(3) . . . . ? C9B C10B C11B C12B -72.8(4) . . . . ? C9B C10B C11B C1B 53.5(4) . . . . ? C2B C1B C11B O2B -62.7(3) . . . . ? C6B C1B C11B O2B 171.4(2) . . . . ? C5B C1B C11B O2B 51.3(3) . . . . ? C2B C1B C11B C12B 178.8(3) . . . . ? C6B C1B C11B C12B 52.9(3) . . . . ? C5B C1B C11B C12B -67.1(3) . . . . ? C2B C1B C11B C10B 52.2(3) . . . . ? C6B C1B C11B C10B -73.7(3) . . . . ? C5B C1B C11B C10B 166.2(3) . . . . ? O2B C11B C12B C13B -171.9(3) . . . . ? C10B C11B C12B C13B 72.3(3) . . . . ? C1B C11B C12B C13B -56.4(4) . . . . ? C11B C12B C13B C14B 56.0(4) . . . . ? O1B C6B C14B C13B 168.9(3) . . . . ? C7B C6B C14B C13B -79.1(3) . . . . ? C1B C6B C14B C13B 52.6(4) . . . . ? C12B C13B C14B C6B -53.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.366 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.088 data_ohj12m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 O2' _chemical_formula_weight 206.27 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 0.0016 '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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.6041(5) _cell_length_b 13.1932(7) _cell_length_c 19.0521(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2162.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 76 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 '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 13115 _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2624 _reflns_number_gt 2278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1003P)^2^+0.8288P] 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 2624 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1589 _refine_ls_wR_factor_gt 0.1503 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _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 0.16240(13) 0.69115(9) 0.04679(5) 0.0313(3) Uani 1 1 d . . . H1 H 0.1075 0.7228 0.0177 0.038 Uiso 1 1 calc R . . O2 O -0.04160(12) 0.82949(9) 0.01079(5) 0.0320(3) Uani 1 1 d . . . H2 H -0.1290 0.8243 -0.0085 0.038 Uiso 1 1 calc R . . C1 C 0.09885(16) 0.84021(10) 0.11950(7) 0.0229(3) Uani 1 1 d . . . C2 C 0.12351(17) 0.72392(11) 0.11719(7) 0.0264(3) Uani 1 1 d . . . C3 C -0.03753(19) 0.68120(11) 0.13747(9) 0.0324(4) Uani 1 1 d . . . H3A H -0.0410 0.6645 0.1881 0.039 Uiso 1 1 calc R . . H3B H -0.0609 0.6192 0.1102 0.039 Uiso 1 1 calc R . . C4 C -0.15605(17) 0.76660(12) 0.11982(8) 0.0297(3) Uani 1 1 d . . . H4A H -0.2375 0.7409 0.0877 0.036 Uiso 1 1 calc R . . H4B H -0.2064 0.7918 0.1632 0.036 Uiso 1 1 calc R . . C5 C -0.06191(16) 0.85227(11) 0.08420(7) 0.0253(3) Uani 1 1 d . . . C6 C -0.13258(18) 0.95817(12) 0.09105(9) 0.0335(4) Uani 1 1 d . . . H6A H -0.0822 1.0038 0.0566 0.040 Uiso 1 1 calc R . . H6B H -0.2445 0.9547 0.0793 0.040 Uiso 1 1 calc R . . C7 C -0.11467(19) 1.00225(12) 0.16286(9) 0.0357(4) Uani 1 1 d . . . H7A H -0.1770 1.0588 0.1755 0.043 Uiso 1 1 calc R . . C8 C -0.01523(19) 0.96565(12) 0.20979(9) 0.0324(4) Uani 1 1 d . . . H8A H -0.0078 0.9990 0.2539 0.039 Uiso 1 1 calc R . . C9 C 0.08614(18) 0.87475(12) 0.19734(7) 0.0282(3) Uani 1 1 d . . . H9A H 0.0452 0.8175 0.2254 0.034 Uiso 1 1 calc R . . H9B H 0.1919 0.8901 0.2149 0.034 Uiso 1 1 calc R . . C10 C 0.23700(17) 0.89337(12) 0.08444(8) 0.0301(3) Uani 1 1 d . . . H10A H 0.2304 0.8850 0.0329 0.036 Uiso 1 1 calc R . . H10B H 0.2340 0.9668 0.0952 0.036 Uiso 1 1 calc R . . C11 C 0.38824(18) 0.84827(14) 0.11106(9) 0.0366(4) Uani 1 1 d . . . H11A H 0.4812 0.8854 0.1032 0.044 Uiso 1 1 calc R . . C12 C 0.39926(19) 0.76049(14) 0.14456(9) 0.0381(4) Uani 1 1 d . . . H12A H 0.4996 0.7387 0.1589 0.046 Uiso 1 1 calc R . . C13 C 0.2633(2) 0.69312(13) 0.16136(9) 0.0358(4) Uani 1 1 d . . . H13A H 0.2372 0.6989 0.2118 0.043 Uiso 1 1 calc R . . H13B H 0.2907 0.6217 0.1515 0.043 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 0.0282(6) 0.0388(6) 0.0268(6) -0.0105(4) 0.0012(4) 0.0019(4) O2 0.0252(5) 0.0496(7) 0.0211(5) 0.0003(4) -0.0026(4) -0.0036(5) C1 0.0217(6) 0.0270(6) 0.0199(6) -0.0010(5) 0.0000(5) -0.0011(5) C2 0.0267(7) 0.0274(7) 0.0251(7) -0.0025(5) 0.0016(5) 0.0010(5) C3 0.0336(8) 0.0282(7) 0.0354(8) 0.0012(6) 0.0065(6) -0.0039(6) C4 0.0239(7) 0.0350(8) 0.0303(8) 0.0011(6) 0.0041(5) -0.0056(6) C5 0.0212(6) 0.0332(7) 0.0215(7) 0.0018(5) 0.0014(5) -0.0026(5) C6 0.0269(7) 0.0358(8) 0.0379(9) 0.0086(6) 0.0012(6) 0.0042(6) C7 0.0329(8) 0.0278(7) 0.0463(10) 0.0000(6) 0.0089(7) 0.0035(6) C8 0.0339(8) 0.0306(7) 0.0327(8) -0.0084(6) 0.0077(6) -0.0029(6) C9 0.0287(7) 0.0314(7) 0.0245(7) -0.0032(6) 0.0004(5) 0.0018(6) C10 0.0264(7) 0.0336(8) 0.0303(7) -0.0028(6) 0.0045(5) -0.0070(6) C11 0.0217(7) 0.0515(10) 0.0367(9) -0.0163(7) 0.0019(6) -0.0062(6) C12 0.0260(8) 0.0520(10) 0.0363(9) -0.0149(7) -0.0055(6) 0.0076(7) C13 0.0357(8) 0.0368(8) 0.0348(8) -0.0038(6) -0.0048(6) 0.0110(6) _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 1.4482(17) . ? O2 C5 1.4412(17) . ? C1 C10 1.5333(19) . ? C1 C5 1.5462(19) . ? C1 C2 1.5496(19) . ? C1 C9 1.5554(19) . ? C2 C13 1.523(2) . ? C2 C3 1.545(2) . ? C3 C4 1.556(2) . ? C4 C5 1.547(2) . ? C5 C6 1.529(2) . ? C6 C7 1.495(2) . ? C7 C8 1.328(2) . ? C8 C9 1.502(2) . ? C10 C11 1.518(2) . ? C11 C12 1.326(3) . ? C12 C13 1.504(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 C10 C1 C5 117.19(12) . . ? C10 C1 C2 109.53(12) . . ? C5 C1 C2 102.24(11) . . ? C10 C1 C9 109.63(12) . . ? C5 C1 C9 108.76(11) . . ? C2 C1 C9 109.08(11) . . ? O1 C2 C13 104.46(12) . . ? O1 C2 C3 109.27(12) . . ? C13 C2 C3 118.21(13) . . ? O1 C2 C1 110.70(12) . . ? C13 C2 C1 110.89(12) . . ? C3 C2 C1 103.37(11) . . ? C2 C3 C4 105.64(11) . . ? C5 C4 C3 106.29(11) . . ? O2 C5 C6 108.76(12) . . ? O2 C5 C4 109.68(12) . . ? C6 C5 C4 114.95(12) . . ? O2 C5 C1 106.99(11) . . ? C6 C5 C1 114.37(12) . . ? C4 C5 C1 101.68(11) . . ? C7 C6 C5 113.12(13) . . ? C8 C7 C6 122.76(14) . . ? C7 C8 C9 123.92(14) . . ? C8 C9 C1 115.18(12) . . ? C11 C10 C1 109.86(13) . . ? C12 C11 C10 124.37(14) . . ? C11 C12 C13 124.28(15) . . ? C12 C13 C2 109.82(14) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.414 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.072