data_jyc02 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H22 O3' _chemical_formula_sum 'C13 H22 O3' _chemical_formula_weight 226.31 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 8.3489(4) _cell_length_b 7.3054(3) _cell_length_c 9.9944(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.627(3) _cell_angle_gamma 90.00 _cell_volume 587.05(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5677 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 36.05 _exptl_crystal_description Column _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9807 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KAPPA APEX II' _diffrn_measurement_method '\w scans; 9 settings' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17473 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 36.35 _reflns_number_total 5474 _reflns_number_gt 4661 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.7-0' _computing_cell_refinement 'Bruker SAINT-Plus v7.66A' _computing_data_reduction 'Bruker SAINT-Plus v7.66A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker XP v5.1' _computing_publication_material 'Bruker XCIF 2008' _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 matrix' _refine_ls_weighting_scheme Sigma _refine_ls_weighting_details 'w=1/s^2^(Fo^2^)' _atom_sites_solution_primary 'Direct methods' _atom_sites_solution_secondary 'Difference Fourier map' _atom_sites_solution_hydrogens 'Difference Fourier map' _refine_ls_hydrogen_treatment Unrestrained _chemical_absolute_configuration unk _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 -0.2(6) _refine_ls_number_reflns 5474 _refine_ls_number_parameters 233 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0504 _refine_ls_wR_factor_gt 0.0498 _refine_ls_goodness_of_fit_ref 1.709 _refine_ls_restrained_S_all 1.709 _refine_ls_shift/su_max 0.001 _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 0.67151(9) -0.05730(9) 0.72767(7) 0.02197(17) Uani 1 1 d . . . O2 O 0.42598(8) 0.06825(9) 0.70456(7) 0.01766(15) Uani 1 1 d . . . O3 O 0.49407(9) 0.63849(10) 0.59167(7) 0.02109(17) Uani 1 1 d . . . C1 C 0.59076(12) 0.08197(14) 0.72039(9) 0.0167(2) Uani 1 1 d . . . C2 C 0.65861(13) 0.27199(13) 0.73317(11) 0.0184(2) Uani 1 1 d . . . C3 C 0.58358(12) 0.38742(14) 0.82858(10) 0.0158(2) Uani 1 1 d . . . C4 C 0.38971(12) 0.37932(12) 0.79011(9) 0.01301(18) Uani 1 1 d . . . C5 C 0.33220(13) 0.23946(14) 0.67321(10) 0.01553(19) Uani 1 1 d . . . C6 C 0.34320(13) 0.31146(15) 0.92039(9) 0.0160(2) Uani 1 1 d . . . C7 C 0.16013(13) 0.32179(14) 0.91271(10) 0.0186(2) Uani 1 1 d . . . C8 C 0.10233(13) 0.51947(13) 0.88836(10) 0.0162(2) Uani 1 1 d . . . C9 C 0.12837(11) 0.60311(13) 0.75441(9) 0.01442(18) Uani 1 1 d . . . C10 C 0.31063(12) 0.57312(13) 0.74620(9) 0.01264(18) Uani 1 1 d . . . C11 C 0.32802(13) 0.63761(14) 0.60382(9) 0.0168(2) Uani 1 1 d . . . C12 C -0.00357(14) 0.52505(16) 0.62838(11) 0.0199(2) Uani 1 1 d . . . C13 C 0.09376(14) 0.81028(14) 0.76034(11) 0.0205(2) Uani 1 1 d . . . H3 H 0.5343(16) 0.7264(17) 0.6308(13) 0.038(4) Uiso 1 1 d . . . H2A H 0.6355(12) 0.3286(14) 0.6419(11) 0.018(3) Uiso 1 1 d . . . H2B H 0.7754(13) 0.2629(13) 0.7687(10) 0.018(3) Uiso 1 1 d . . . H3A H 0.6191(13) 0.5112(14) 0.8255(10) 0.019(3) Uiso 1 1 d . . . H3B H 0.6263(12) 0.3407(14) 0.9218(11) 0.019(3) Uiso 1 1 d . . . H5A H 0.2155(13) 0.2052(13) 0.6656(10) 0.016(3) Uiso 1 1 d . . . H5B H 0.3458(12) 0.2861(13) 0.5863(10) 0.013(3) Uiso 1 1 d . . . H6A H 0.4038(12) 0.3843(13) 0.9990(10) 0.016(3) Uiso 1 1 d . . . H6B H 0.3868(13) 0.1889(14) 0.9408(11) 0.026(3) Uiso 1 1 d . . . H7A H 0.0898(12) 0.2361(13) 0.8392(10) 0.015(3) Uiso 1 1 d . . . H7B H 0.1405(13) 0.2780(15) 1.0024(11) 0.028(3) Uiso 1 1 d . . . H8A H 0.1609(12) 0.5927(15) 0.9680(10) 0.015(2) Uiso 1 1 d . . . H8B H -0.0081(13) 0.5306(12) 0.8868(10) 0.012(3) Uiso 1 1 d . . . H10 H 0.3709(12) 0.6580(12) 0.8147(10) 0.010(3) Uiso 1 1 d . . . H11A H 0.2608(12) 0.5509(14) 0.5287(10) 0.014(3) Uiso 1 1 d . . . H11B H 0.2749(12) 0.7663(13) 0.5842(9) 0.014(3) Uiso 1 1 d . . . H12A H 0.0025(13) 0.3944(16) 0.6195(11) 0.027(3) Uiso 1 1 d . . . H12B H 0.0099(13) 0.5811(16) 0.5453(10) 0.020(3) Uiso 1 1 d . . . H12C H -0.1080(15) 0.5566(15) 0.6397(10) 0.027(3) Uiso 1 1 d . . . H13A H -0.0115(13) 0.8302(14) 0.7776(10) 0.016(3) Uiso 1 1 d . . . H13B H 0.0990(13) 0.8688(14) 0.6789(11) 0.026(3) Uiso 1 1 d . . . H13C H 0.1749(13) 0.8684(14) 0.8399(11) 0.022(3) Uiso 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 0.0188(4) 0.0184(4) 0.0282(4) -0.0009(3) 0.0054(3) 0.0043(3) O2 0.0152(4) 0.0148(4) 0.0242(3) -0.0022(3) 0.0072(3) 0.0009(3) O3 0.0218(4) 0.0219(4) 0.0233(4) -0.0010(3) 0.0125(3) -0.0028(3) C1 0.0161(5) 0.0199(5) 0.0147(4) -0.0020(4) 0.0055(3) -0.0006(4) C2 0.0125(5) 0.0214(6) 0.0217(5) -0.0039(4) 0.0051(4) -0.0006(4) C3 0.0128(5) 0.0180(5) 0.0165(4) -0.0017(4) 0.0039(3) -0.0009(4) C4 0.0115(5) 0.0142(4) 0.0132(4) -0.0007(3) 0.0031(3) 0.0003(4) C5 0.0135(5) 0.0153(5) 0.0174(4) -0.0029(4) 0.0037(4) 0.0005(4) C6 0.0186(5) 0.0155(5) 0.0139(4) 0.0023(4) 0.0042(4) 0.0024(4) C7 0.0213(5) 0.0182(5) 0.0194(4) 0.0039(4) 0.0106(4) 0.0007(4) C8 0.0153(5) 0.0182(5) 0.0168(4) -0.0019(4) 0.0074(4) 0.0007(4) C9 0.0143(5) 0.0150(4) 0.0141(4) 0.0002(4) 0.0040(3) 0.0000(4) C10 0.0133(5) 0.0131(4) 0.0113(4) -0.0023(3) 0.0029(3) -0.0017(4) C11 0.0184(5) 0.0173(5) 0.0155(4) 0.0020(4) 0.0062(4) -0.0011(4) C12 0.0136(5) 0.0248(6) 0.0193(5) 0.0006(4) 0.0011(4) 0.0000(4) C13 0.0198(6) 0.0177(5) 0.0240(5) 0.0024(4) 0.0063(4) 0.0038(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 1.2118(12) . ? O2 C1 1.3455(11) . ? O2 C5 1.4640(12) . ? O3 C11 1.4239(12) . ? O3 H3 0.780(12) . ? C1 C2 1.4917(14) . ? C2 C3 1.5280(14) . ? C2 H2A 0.972(10) . ? C2 H2B 0.946(10) . ? C3 C4 1.5608(13) . ? C3 H3A 0.954(10) . ? C3 H3B 0.966(10) . ? C4 C5 1.5288(13) . ? C4 C6 1.5377(13) . ? C4 C10 1.5737(13) . ? C5 H5A 0.989(11) . ? C5 H5B 0.968(9) . ? C6 C7 1.5115(14) . ? C6 H6A 0.971(10) . ? C6 H6B 0.967(10) . ? C7 C8 1.5213(14) . ? C7 H7A 1.022(10) . ? C7 H7B 1.006(11) . ? C8 C9 1.5394(13) . ? C8 H8A 0.974(10) . ? C8 H8B 0.921(11) . ? C9 C12 1.5420(13) . ? C9 C13 1.5449(14) . ? C9 C10 1.5613(13) . ? C10 C11 1.5425(12) . ? C10 H10 0.960(9) . ? C11 H11A 1.026(10) . ? C11 H11B 1.036(10) . ? C12 H12A 0.961(12) . ? C12 H12B 0.960(10) . ? C12 H12C 0.938(12) . ? C13 H13A 0.952(11) . ? C13 H13B 0.931(11) . ? C13 H13C 0.991(10) . ? 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 C5 115.62(8) . . ? C11 O3 H3 105.0(10) . . ? O1 C1 O2 118.63(9) . . ? O1 C1 C2 125.72(9) . . ? O2 C1 C2 115.60(9) . . ? C1 C2 C3 110.91(9) . . ? C1 C2 H2A 109.9(6) . . ? C3 C2 H2A 109.8(6) . . ? C1 C2 H2B 107.2(6) . . ? C3 C2 H2B 111.1(6) . . ? H2A C2 H2B 107.8(8) . . ? C2 C3 C4 113.43(8) . . ? C2 C3 H3A 108.7(7) . . ? C4 C3 H3A 109.8(6) . . ? C2 C3 H3B 107.5(6) . . ? C4 C3 H3B 108.2(6) . . ? H3A C3 H3B 109.2(8) . . ? C5 C4 C6 109.43(8) . . ? C5 C4 C3 107.76(8) . . ? C6 C4 C3 106.58(7) . . ? C5 C4 C10 111.49(7) . . ? C6 C4 C10 110.09(8) . . ? C3 C4 C10 111.34(8) . . ? O2 C5 C4 111.57(7) . . ? O2 C5 H5A 105.0(6) . . ? C4 C5 H5A 109.2(6) . . ? O2 C5 H5B 107.9(6) . . ? C4 C5 H5B 111.2(6) . . ? H5A C5 H5B 111.8(8) . . ? C7 C6 C4 115.05(8) . . ? C7 C6 H6A 108.3(6) . . ? C4 C6 H6A 108.2(6) . . ? C7 C6 H6B 112.0(7) . . ? C4 C6 H6B 108.1(7) . . ? H6A C6 H6B 104.6(8) . . ? C6 C7 C8 109.17(9) . . ? C6 C7 H7A 112.5(6) . . ? C8 C7 H7A 111.7(5) . . ? C6 C7 H7B 110.1(6) . . ? C8 C7 H7B 108.9(6) . . ? H7A C7 H7B 104.2(8) . . ? C7 C8 C9 113.76(8) . . ? C7 C8 H8A 108.8(6) . . ? C9 C8 H8A 109.6(6) . . ? C7 C8 H8B 111.0(6) . . ? C9 C8 H8B 109.0(6) . . ? H8A C8 H8B 104.2(8) . . ? C8 C9 C12 109.05(8) . . ? C8 C9 C13 106.48(8) . . ? C12 C9 C13 107.08(8) . . ? C8 C9 C10 110.98(7) . . ? C12 C9 C10 113.40(8) . . ? C13 C9 C10 109.54(8) . . ? C11 C10 C9 109.93(7) . . ? C11 C10 C4 113.29(8) . . ? C9 C10 C4 116.95(8) . . ? C11 C10 H10 107.4(6) . . ? C9 C10 H10 101.7(6) . . ? C4 C10 H10 106.4(5) . . ? O3 C11 C10 114.57(8) . . ? O3 C11 H11A 107.1(6) . . ? C10 C11 H11A 108.5(6) . . ? O3 C11 H11B 110.9(6) . . ? C10 C11 H11B 108.1(5) . . ? H11A C11 H11B 107.5(7) . . ? C9 C12 H12A 113.5(6) . . ? C9 C12 H12B 108.9(6) . . ? H12A C12 H12B 108.8(9) . . ? C9 C12 H12C 107.1(6) . . ? H12A C12 H12C 109.2(9) . . ? H12B C12 H12C 109.2(9) . . ? C9 C13 H13A 110.4(6) . . ? C9 C13 H13B 111.3(6) . . ? H13A C13 H13B 110.6(9) . . ? C9 C13 H13C 110.9(6) . . ? H13A C13 H13C 104.7(8) . . ? H13B C13 H13C 108.8(9) . . ? 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 O3 H3 O1 0.780(12) 2.037(12) 2.8100(10) 171.5(13) 1_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 36.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.380 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.047