data_shelxl _audit_creation_method SHELXL-97 _publ_section_references ; CrystalClear, Rigaku Corp., (1999) Altomare, A., M. Burla, M. Camalli, G. Cascarano, C. Giacovazzo A. Guagliardi, A. Moliterni, G. Polidori & R. Spagna. (1999) J. Appl. Cryst. 32, 115-119. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H20 O3' _chemical_formula_weight 200.27 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 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 12.7220(15) _cell_length_b 13.0859(15) _cell_length_c 14.9523(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2489.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.069 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8379 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method 'phi and omega rotations' _diffrn_reflns_number 8368 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.34 _reflns_number_total 4412 _reflns_number_gt 3840 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 1999)' _computing_data_reduction 'CrystalClear (Rigaku, 1999)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0718P)^2^+0.3627P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _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 0.5(11) _refine_ls_number_reflns 4412 _refine_ls_number_parameters 273 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1268 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.075 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.53444(17) 0.63377(16) 0.28338(15) 0.0402(5) Uani 1 1 d . . . C2 C 0.46174(17) 0.72395(15) 0.27112(15) 0.0408(5) Uani 1 1 d . . . H2 H 0.4537 0.7589 0.3287 0.054 Uiso 1 1 calc R . . C3 C 0.35371(18) 0.68641(16) 0.24004(13) 0.0395(5) Uani 1 1 d . . . H3 H 0.3644 0.6507 0.1832 0.053 Uiso 1 1 calc R . . C4 C 0.29881(17) 0.61194(16) 0.30271(13) 0.0389(5) Uani 1 1 d . . . H4 H 0.3495 0.5584 0.3181 0.052 Uiso 1 1 calc R . . C5 C 0.2639(2) 0.66281(18) 0.39014(15) 0.0465(5) Uani 1 1 d . . . H5A H 0.3202 0.7069 0.4109 0.062 Uiso 1 1 calc R . . H5B H 0.2036 0.7058 0.3776 0.062 Uiso 1 1 calc R . . C6 C 0.2350(2) 0.58950(19) 0.46523(15) 0.0500(6) Uani 1 1 d . . . H6 H 0.1833 0.5403 0.4427 0.067 Uiso 1 1 calc R . . C7 C 0.3304(3) 0.5327(3) 0.4961(2) 0.0846(10) Uani 1 1 d . . . H7 H 0.3847 0.5725 0.5188 0.112 Uiso 1 1 calc R . . C8 C 0.3464(5) 0.4368(4) 0.4954(3) 0.1308(19) Uani 1 1 d . . . H8A H 0.2950 0.3929 0.4736 0.174 Uiso 1 1 calc R . . H8B H 0.4096 0.4106 0.5167 0.174 Uiso 1 1 calc R . . C9 C 0.5133(2) 0.79781(19) 0.2043(2) 0.0651(7) Uani 1 1 d . . . H9A H 0.5798 0.8202 0.2275 0.098 Uiso 1 1 calc R . . H9B H 0.4684 0.8558 0.1954 0.098 Uiso 1 1 calc R . . H9C H 0.5240 0.7635 0.1483 0.098 Uiso 1 1 calc R . . C10 C 0.2061(2) 0.5607(2) 0.25654(18) 0.0656(7) Uani 1 1 d . . . H10A H 0.1536 0.6110 0.2429 0.098 Uiso 1 1 calc R . . H10B H 0.1767 0.5098 0.2954 0.098 Uiso 1 1 calc R . . H10C H 0.2296 0.5289 0.2022 0.098 Uiso 1 1 calc R . . C11 C 0.1861(3) 0.6492(3) 0.5431(2) 0.0782(9) Uani 1 1 d . . . H11A H 0.1623 0.6022 0.5880 0.117 Uiso 1 1 calc R . . H11B H 0.1276 0.6885 0.5216 0.117 Uiso 1 1 calc R . . H11C H 0.2378 0.6942 0.5683 0.117 Uiso 1 1 calc R . . O1 O 0.58094(15) 0.63165(13) 0.36231(11) 0.0584(5) Uani 1 1 d . . . H1 H 0.6264 0.5872 0.3625 0.088 Uiso 1 1 calc R . . O2 O 0.54994(13) 0.57036(12) 0.22566(11) 0.0517(4) Uani 1 1 d . . . O3 O 0.28612(14) 0.77264(11) 0.22193(10) 0.0504(4) Uani 1 1 d . . . H3A H 0.2886 0.8127 0.2640 0.076 Uiso 1 1 calc R . . C1' C 0.77462(16) 0.43321(16) 0.43991(13) 0.0383(5) Uani 1 1 d . . . C2' C 0.83140(17) 0.47588(16) 0.51999(14) 0.0410(5) Uani 1 1 d . . . H2' H 0.8601 0.4188 0.5547 0.055 Uiso 1 1 calc R . . C3' C 0.75650(16) 0.53655(14) 0.58000(14) 0.0355(4) Uani 1 1 d . . . H3' H 0.7312 0.5945 0.5445 0.047 Uiso 1 1 calc R . . C4' C 0.65924(17) 0.47838(16) 0.61206(15) 0.0418(5) Uani 1 1 d . . . H4' H 0.6257 0.4480 0.5594 0.056 Uiso 1 1 calc R . . C5' C 0.6873(2) 0.39085(19) 0.67636(18) 0.0556(6) Uani 1 1 d . B . H5A' H 0.7500 0.3574 0.6537 0.074 Uiso 1 1 calc R . . H5A' H 0.7053 0.4207 0.7337 0.074 Uiso 1 1 calc R . . C6' C 0.6062(2) 0.3110(2) 0.6920(2) 0.0762(9) Uani 1 1 d D . . H6' H 0.5344 0.3380 0.6944 0.101 Uiso 1 1 calc R A 1 C7' C 0.6271(4) 0.2417(4) 0.6093(3) 0.0685(14) Uani 0.55 1 d PD B 1 H7' H 0.6933 0.2121 0.6043 0.091 Uiso 0.55 1 calc PR B 1 C7" C 0.5372(5) 0.2599(5) 0.6283(4) 0.082(2) Uani 0.45 1 d PD B 2 H7" H 0.4677 0.2524 0.6463 0.110 Uiso 0.45 1 calc PR B 2 C8' C 0.5602(4) 0.2225(4) 0.5479(3) 0.1135(15) Uani 1 1 d D . . H8A' H 0.4933 0.2508 0.5507 0.151 Uiso 0.55 1 calc PR B 1 H8B' H 0.5785 0.1803 0.5004 0.151 Uiso 0.55 1 calc PR B 1 H8A" H 0.6284 0.2275 0.5258 0.151 Uiso 0.45 1 calc PR B 2 H8B" H 0.5082 0.1914 0.5137 0.151 Uiso 0.45 1 calc PR B 2 C9' C 0.9227(2) 0.5418(3) 0.4870(2) 0.0715(8) Uani 1 1 d . . . H9A' H 0.9679 0.5014 0.4495 0.107 Uiso 1 1 calc R . . H9B' H 0.9619 0.5667 0.5373 0.107 Uiso 1 1 calc R . . H9C' H 0.8958 0.5985 0.4533 0.107 Uiso 1 1 calc R . . C10' C 0.5808(2) 0.5521(2) 0.6538(2) 0.0659(7) Uani 1 1 d . . . H10D H 0.5172 0.5161 0.6681 0.099 Uiso 1 1 calc R . . H10E H 0.5655 0.6060 0.6123 0.099 Uiso 1 1 calc R . . H10F H 0.6102 0.5806 0.7074 0.099 Uiso 1 1 calc R . . C11' C 0.6337(4) 0.2424(3) 0.7705(3) 0.1066(14) Uani 1 1 d . B . H11D H 0.5762 0.1969 0.7824 0.160 Uiso 1 1 calc R . . H11E H 0.6469 0.2837 0.8224 0.160 Uiso 1 1 calc R . . H11F H 0.6954 0.2034 0.7565 0.160 Uiso 1 1 calc R . . O1' O 0.79019(14) 0.33532(11) 0.42734(11) 0.0483(4) Uani 1 1 d . . . H1' H 0.7603 0.3172 0.3814 0.072 Uiso 1 1 calc R . . O2' O 0.72173(16) 0.48414(14) 0.38949(11) 0.0624(5) Uani 1 1 d . . . O3' O 0.81506(12) 0.57860(10) 0.65385(10) 0.0414(4) Uani 1 1 d . . . H3A' H 0.8502 0.5334 0.6772 0.062 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 C1 0.0393(11) 0.0367(10) 0.0447(12) 0.0005(9) 0.0059(10) 0.0001(9) C2 0.0488(12) 0.0348(10) 0.0388(11) 0.0017(9) 0.0059(10) 0.0064(10) C3 0.0524(12) 0.0346(10) 0.0315(10) -0.0033(8) -0.0012(9) 0.0144(10) C4 0.0446(11) 0.0344(9) 0.0375(10) -0.0050(8) -0.0048(9) 0.0056(10) C5 0.0518(13) 0.0445(12) 0.0431(12) -0.0061(10) 0.0008(10) -0.0027(11) C6 0.0486(13) 0.0583(14) 0.0432(12) -0.0014(11) 0.0023(10) -0.0054(12) C7 0.081(2) 0.116(3) 0.0564(16) 0.0261(18) 0.0025(15) 0.014(2) C8 0.175(5) 0.111(3) 0.107(3) 0.030(3) 0.007(3) 0.061(4) C9 0.0761(18) 0.0452(13) 0.0740(18) 0.0161(13) 0.0161(15) 0.0051(13) C10 0.0653(16) 0.0697(17) 0.0618(16) -0.0165(13) -0.0127(14) -0.0123(14) C11 0.087(2) 0.091(2) 0.0567(15) -0.0104(15) 0.0201(16) -0.0176(19) O1 0.0690(11) 0.0518(10) 0.0546(10) -0.0095(8) -0.0141(9) 0.0213(9) O2 0.0572(10) 0.0470(8) 0.0508(9) -0.0084(8) 0.0062(8) 0.0172(8) O3 0.0683(10) 0.0419(8) 0.0409(8) -0.0020(7) -0.0110(8) 0.0221(8) C1' 0.0369(10) 0.0416(11) 0.0364(10) 0.0010(9) -0.0010(9) 0.0049(9) C2' 0.0395(11) 0.0366(10) 0.0469(12) -0.0032(9) -0.0081(9) 0.0030(10) C3' 0.0386(10) 0.0285(9) 0.0393(10) -0.0008(8) -0.0104(9) 0.0024(9) C4' 0.0393(11) 0.0379(10) 0.0483(11) -0.0059(9) -0.0047(9) 0.0008(10) C5' 0.0565(14) 0.0495(13) 0.0607(14) 0.0111(12) -0.0084(12) -0.0138(12) C6' 0.0620(17) 0.0652(17) 0.101(2) 0.0242(17) -0.0014(16) -0.0176(15) C7' 0.068(3) 0.047(3) 0.090(4) -0.003(3) -0.004(3) -0.005(3) C7" 0.055(4) 0.066(4) 0.126(7) 0.037(4) -0.020(4) -0.017(3) C8' 0.115(3) 0.139(4) 0.087(3) 0.022(3) -0.005(3) -0.011(3) C9' 0.0511(15) 0.084(2) 0.0800(19) -0.0154(17) 0.0139(14) -0.0193(15) C10' 0.0517(14) 0.0622(16) 0.0839(19) -0.0183(15) 0.0144(14) 0.0017(13) C11' 0.151(4) 0.083(2) 0.086(2) 0.032(2) 0.002(3) -0.039(3) O1' 0.0602(10) 0.0380(8) 0.0466(9) -0.0041(7) -0.0160(8) 0.0009(7) O2' 0.0774(12) 0.0595(10) 0.0504(9) -0.0022(8) -0.0209(9) 0.0253(10) O3' 0.0483(9) 0.0296(7) 0.0463(8) -0.0051(6) -0.0143(7) -0.0009(7) _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 C1 O2 1.213(3) . ? C1 O1 1.320(3) . ? C1 C2 1.511(3) . ? C2 C3 1.532(3) . ? C2 C9 1.537(3) . ? C3 O3 1.444(2) . ? C3 C4 1.522(3) . ? C4 C10 1.522(3) . ? C4 C5 1.533(3) . ? C5 C6 1.522(3) . ? C6 C7 1.496(4) . ? C6 C11 1.534(4) . ? C7 C8 1.271(5) . ? C1' O2' 1.211(3) . ? C1' O1' 1.310(3) . ? C1' C2' 1.506(3) . ? C2' C9' 1.529(3) . ? C2' C3' 1.531(3) . ? C3' O3' 1.441(2) . ? C3' C4' 1.530(3) . ? C4' C10' 1.522(3) . ? C4' C5' 1.537(3) . ? C5' C6' 1.487(4) . ? C6' C7" 1.457(4) . ? C6' C11' 1.519(5) . ? C6' C7' 1.555(4) . ? C7' C8' 1.277(4) . ? C7" C8' 1.331(5) . ? 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 O2 C1 O1 123.3(2) . . ? O2 C1 C2 123.2(2) . . ? O1 C1 C2 113.53(19) . . ? C1 C2 C3 109.62(17) . . ? C1 C2 C9 107.98(18) . . ? C3 C2 C9 112.8(2) . . ? O3 C3 C4 110.03(18) . . ? O3 C3 C2 109.91(17) . . ? C4 C3 C2 115.49(17) . . ? C3 C4 C10 111.01(19) . . ? C3 C4 C5 112.34(17) . . ? C10 C4 C5 110.7(2) . . ? C6 C5 C4 115.18(19) . . ? C7 C6 C5 110.2(2) . . ? C7 C6 C11 110.3(2) . . ? C5 C6 C11 109.7(2) . . ? C8 C7 C6 128.2(5) . . ? O2' C1' O1' 122.2(2) . . ? O2' C1' C2' 123.9(2) . . ? O1' C1' C2' 113.84(18) . . ? C1' C2' C9' 108.5(2) . . ? C1' C2' C3' 111.08(17) . . ? C9' C2' C3' 111.71(19) . . ? O3' C3' C4' 111.60(17) . . ? O3' C3' C2' 108.98(16) . . ? C4' C3' C2' 115.41(16) . . ? C10' C4' C3' 110.11(19) . . ? C10' C4' C5' 111.6(2) . . ? C3' C4' C5' 112.26(18) . . ? C6' C5' C4' 117.4(2) . . ? C7" C6' C5' 129.6(4) . . ? C7" C6' C11' 111.9(4) . . ? C5' C6' C11' 112.1(3) . . ? C7" C6' C7' 46.9(4) . . ? C5' C6' C7' 99.6(3) . . ? C11' C6' C7' 103.4(3) . . ? C8' C7' C6' 124.9(5) . . ? C8' C7" C6' 128.8(5) . . ? C7' C8' C7" 54.9(4) . . ? 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 O1 H1 O2' 0.82 1.86 2.664(2) 167.3 . O3 H3A O3' 0.82 1.91 2.716(2) 167.7 2_466 O1' H1' O3 0.82 1.75 2.568(2) 172.0 3_645 O3' H3A' O2 0.82 2.00 2.811(2) 173.2 4_665 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.260 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.037