data_d09014 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 O4' _chemical_formula_weight 228.28 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 '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 10.4928(3) _cell_length_b 5.17550(10) _cell_length_c 11.2885(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.4120(10) _cell_angle_gamma 90.00 _cell_volume 566.72(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9709 _cell_measurement_theta_min 4.24 _cell_measurement_theta_max 68.44 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6959 _exptl_absorpt_correction_T_max 0.9230 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; 'Bruker three-circle diffractometer, Bruker APEX CCD' ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 10799 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0118 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.24 _diffrn_reflns_theta_max 67.66 _reflns_number_total 2028 _reflns_number_gt 2005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 3.0 (Bruker-AXS, 2008)' _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2008)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0503P)^2^+0.0865P] 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 0.0103(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(13) _refine_ls_number_reflns 2028 _refine_ls_number_parameters 150 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.101 _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 0.36236(7) 0.46642(18) 0.76029(7) 0.0170(2) Uani 1 1 d . . . O2 O 0.33137(7) 0.80928(15) 0.46470(7) 0.0151(2) Uani 1 1 d . . . O3 O -0.00301(7) 0.47310(16) 0.34327(7) 0.0144(2) Uani 1 1 d . . . O4 O -0.02720(8) 0.76477(19) 0.04092(7) 0.0179(2) Uani 1 1 d D . . H4 H -0.0149(15) 0.911(3) 0.0209(14) 0.022 Uiso 1 1 d D . . C1 C 0.50693(11) 0.5023(3) 0.83296(11) 0.0188(3) Uani 1 1 d . . . H1A H 0.5596 0.3702 0.8071 0.023 Uiso 1 1 calc R . . H1B H 0.5259 0.4773 0.9251 0.023 Uiso 1 1 calc R . . C2 C 0.55583(11) 0.7711(3) 0.81308(11) 0.0194(3) Uani 1 1 d . . . H2A H 0.6568 0.7844 0.8600 0.023 Uiso 1 1 calc R . . H2B H 0.5113 0.9034 0.8477 0.023 Uiso 1 1 calc R . . C3 C 0.51972(11) 0.8208(2) 0.67013(11) 0.0171(3) Uani 1 1 d . . . H3A H 0.5433 1.0008 0.6568 0.021 Uiso 1 1 calc R . . H3B H 0.5729 0.7026 0.6373 0.021 Uiso 1 1 calc R . . C4 C 0.36640(11) 0.7752(2) 0.59939(11) 0.0151(3) Uani 1 1 d . . . H4A H 0.3140 0.9033 0.6295 0.018 Uiso 1 1 calc R . . C5 C 0.32843(11) 0.5011(2) 0.62626(10) 0.0143(3) Uani 1 1 d . . . H5 H 0.3810 0.3730 0.5964 0.017 Uiso 1 1 calc R . . C6 C 0.17449(11) 0.4540(3) 0.55541(10) 0.0149(3) Uani 1 1 d . . . H6A H 0.1509 0.2742 0.5690 0.018 Uiso 1 1 calc R . . H6B H 0.1207 0.5731 0.5871 0.018 Uiso 1 1 calc R . . C7 C 0.14201(11) 0.5017(2) 0.41443(10) 0.0132(3) Uani 1 1 d . . . H7 H 0.1926 0.3722 0.3830 0.016 Uiso 1 1 calc R . . C8 C 0.18702(10) 0.7744(2) 0.39372(11) 0.0143(3) Uani 1 1 d . . . H8 H 0.1346 0.9042 0.4229 0.017 Uiso 1 1 calc R . . C9 C 0.15609(12) 0.8150(2) 0.25273(11) 0.0153(3) Uani 1 1 d . . . H9A H 0.2131 0.6966 0.2245 0.018 Uiso 1 1 calc R . . H9B H 0.1788 0.9947 0.2380 0.018 Uiso 1 1 calc R . . C10 C 0.00319(11) 0.7624(2) 0.17572(10) 0.0149(3) Uani 1 1 d . . . H10 H -0.0534 0.8974 0.1964 0.018 Uiso 1 1 calc R . . C11 C -0.03810(11) 0.4944(2) 0.20777(10) 0.0142(3) Uani 1 1 d . . . H11 H 0.0135 0.3596 0.1807 0.017 Uiso 1 1 calc R . . C12 C -0.19136(11) 0.4438(3) 0.14120(10) 0.0188(3) Uani 1 1 d . . . H12A H -0.2138 0.2764 0.1689 0.028 Uiso 1 1 calc R . . H12B H -0.2164 0.4418 0.0482 0.028 Uiso 1 1 calc R . . H12C H -0.2429 0.5806 0.1634 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 0.0158(4) 0.0205(5) 0.0128(4) 0.0026(4) 0.0033(3) -0.0007(4) O2 0.0146(4) 0.0180(5) 0.0125(4) 0.0007(3) 0.0047(3) -0.0022(3) O3 0.0128(4) 0.0176(5) 0.0122(4) 0.0012(3) 0.0043(3) -0.0013(4) O4 0.0249(4) 0.0161(4) 0.0126(4) 0.0016(4) 0.0068(3) -0.0017(4) C1 0.0168(5) 0.0194(6) 0.0163(5) 0.0014(5) 0.0020(4) -0.0003(5) C2 0.0159(5) 0.0201(7) 0.0189(6) 0.0000(5) 0.0031(4) -0.0020(5) C3 0.0164(5) 0.0160(6) 0.0185(6) -0.0003(5) 0.0062(4) -0.0010(5) C4 0.0157(5) 0.0148(7) 0.0144(6) 0.0011(5) 0.0055(4) 0.0008(5) C5 0.0174(5) 0.0128(6) 0.0132(5) -0.0004(5) 0.0063(4) 0.0008(5) C6 0.0148(5) 0.0152(7) 0.0150(5) 0.0009(5) 0.0061(4) -0.0004(5) C7 0.0130(5) 0.0116(6) 0.0149(5) -0.0010(5) 0.0052(4) 0.0005(5) C8 0.0127(5) 0.0140(7) 0.0164(6) 0.0005(5) 0.0056(4) 0.0002(5) C9 0.0178(5) 0.0134(6) 0.0161(6) 0.0010(5) 0.0079(4) -0.0006(4) C10 0.0174(5) 0.0148(6) 0.0131(5) 0.0009(5) 0.0066(4) 0.0016(5) C11 0.0174(5) 0.0138(6) 0.0118(5) -0.0010(5) 0.0059(4) 0.0010(5) C12 0.0172(5) 0.0222(7) 0.0164(5) 0.0016(5) 0.0056(4) -0.0016(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 C5 1.4274(12) . ? O1 C1 1.4351(13) . ? O2 C8 1.4295(12) . ? O2 C4 1.4325(13) . ? O3 C7 1.4320(12) . ? O3 C11 1.4345(12) . ? O4 C10 1.4308(13) . ? O4 H4 0.814(13) . ? C1 C2 1.5284(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5322(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5172(14) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5346(16) . ? C4 H4A 1.0000 . ? C5 C6 1.5241(14) . ? C5 H5 1.0000 . ? C6 C7 1.5154(14) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5342(15) . ? C7 H7 1.0000 . ? C8 C9 1.5128(15) . ? C8 H8 1.0000 . ? C9 C10 1.5298(14) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5367(16) . ? C10 H10 1.0000 . ? C11 C12 1.5159(15) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 C5 O1 C1 111.82(8) . . ? C8 O2 C4 111.57(8) . . ? C7 O3 C11 112.09(8) . . ? C10 O4 H4 107.9(10) . . ? O1 C1 C2 112.01(9) . . ? O1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? O1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C1 C2 C3 110.20(10) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 108.36(9) . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3B 110.0 . . ? C2 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? O2 C4 C3 109.33(9) . . ? O2 C4 C5 110.05(9) . . ? C3 C4 C5 110.05(10) . . ? O2 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? O1 C5 C6 108.80(8) . . ? O1 C5 C4 110.31(9) . . ? C6 C5 C4 110.31(9) . . ? O1 C5 H5 109.1 . . ? C6 C5 H5 109.1 . . ? C4 C5 H5 109.1 . . ? C7 C6 C5 107.10(9) . . ? C7 C6 H6A 110.3 . . ? C5 C6 H6A 110.3 . . ? C7 C6 H6B 110.3 . . ? C5 C6 H6B 110.3 . . ? H6A C6 H6B 108.5 . . ? O3 C7 C6 109.74(8) . . ? O3 C7 C8 109.42(9) . . ? C6 C7 C8 110.53(9) . . ? O3 C7 H7 109.0 . . ? C6 C7 H7 109.0 . . ? C8 C7 H7 109.0 . . ? O2 C8 C9 109.18(8) . . ? O2 C8 C7 110.66(9) . . ? C9 C8 C7 109.46(9) . . ? O2 C8 H8 109.2 . . ? C9 C8 H8 109.2 . . ? C7 C8 H8 109.2 . . ? C8 C9 C10 109.33(9) . . ? C8 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? C8 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? O4 C10 C9 111.29(9) . . ? O4 C10 C11 106.83(9) . . ? C9 C10 C11 110.82(9) . . ? O4 C10 H10 109.3 . . ? C9 C10 H10 109.3 . . ? C11 C10 H10 109.3 . . ? O3 C11 C12 107.92(8) . . ? O3 C11 C10 109.85(9) . . ? C12 C11 C10 112.35(9) . . ? O3 C11 H11 108.9 . . ? C12 C11 H11 108.9 . . ? C10 C11 H11 108.9 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O4 0.814(13) 2.066(13) 2.8772(7) 174.0(14) 2 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 67.66 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.251 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.037