data_baran376 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 O3' _chemical_formula_sum 'C18 H26 O3' _chemical_formula_weight 290.39 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 Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 14.6942(18) _cell_length_b 9.3324(9) _cell_length_c 11.6047(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1591.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4071 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 26.27 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9762 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details SADABS _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 APEX-I CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12340 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 26.49 _reflns_number_total 3261 _reflns_number_gt 2671 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0444P)^2^+0.2261P] 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 -0.2(11) _refine_ls_number_reflns 3261 _refine_ls_number_parameters 196 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.54479(11) 0.90110(15) 0.61020(12) 0.0278(4) Uani 1 1 d . . . O2 O 0.67224(10) 0.71823(14) 0.67928(11) 0.0229(3) Uani 1 1 d D . . H2 H 0.6320(12) 0.7839(18) 0.680(2) 0.034 Uiso 1 1 d D . . O3 O 0.51861(9) 0.59234(14) 0.54509(11) 0.0229(3) Uani 1 1 d . . . C1 C 0.69750(15) 0.8266(2) 0.38587(19) 0.0267(5) Uani 1 1 d . . . H1A H 0.7507 0.7721 0.3704 0.032 Uiso 1 1 calc R . . C2 C 0.67233(16) 0.9396(2) 0.3010(2) 0.0359(6) Uani 1 1 d . . . H2B H 0.6511 0.8929 0.2292 0.043 Uiso 1 1 calc R . . H2A H 0.7273 0.9962 0.2819 0.043 Uiso 1 1 calc R . . C3 C 0.59886(15) 1.0404(2) 0.34351(19) 0.0269(5) Uani 1 1 d . . . H3A H 0.5710 1.0895 0.2766 0.032 Uiso 1 1 calc R . . H3B H 0.6269 1.1145 0.3932 0.032 Uiso 1 1 calc R . . C4 C 0.52406(14) 0.9629(2) 0.41186(18) 0.0225(4) Uani 1 1 d . . . C5 C 0.57104(13) 0.8851(2) 0.51060(17) 0.0201(4) Uani 1 1 d . . . C6 C 0.65159(13) 0.7957(2) 0.48190(16) 0.0180(4) Uani 1 1 d . . . C7 C 0.67728(13) 0.6717(2) 0.56139(17) 0.0172(4) Uani 1 1 d . . . C8 C 0.77617(13) 0.6183(2) 0.54775(19) 0.0225(4) Uani 1 1 d . . . H8A H 0.8159 0.7030 0.5367 0.027 Uiso 1 1 calc R . . H8B H 0.7946 0.5721 0.6209 0.027 Uiso 1 1 calc R . . C9 C 0.79485(14) 0.5125(2) 0.44883(19) 0.0269(5) Uani 1 1 d . . . H9A H 0.7991 0.5657 0.3752 0.032 Uiso 1 1 calc R . . H9B H 0.8538 0.4639 0.4622 0.032 Uiso 1 1 calc R . . C10 C 0.71878(14) 0.4003(2) 0.44051(18) 0.0256(5) Uani 1 1 d . . . H10A H 0.7310 0.3284 0.3785 0.031 Uiso 1 1 calc R . . C11 C 0.62810(13) 0.4781(2) 0.42162(16) 0.0214(4) Uani 1 1 d . . . H11A H 0.5792 0.4105 0.3998 0.026 Uiso 1 1 calc R . . H11B H 0.6335 0.5532 0.3618 0.026 Uiso 1 1 calc R . . C12 C 0.61106(13) 0.5433(2) 0.54084(16) 0.0177(4) Uani 1 1 d . . . C13 C 0.63243(14) 0.4159(2) 0.62084(18) 0.0245(5) Uani 1 1 d . . . H13A H 0.6567 0.4497 0.6956 0.029 Uiso 1 1 calc R . . H13B H 0.5772 0.3578 0.6350 0.029 Uiso 1 1 calc R . . C14 C 0.70355(14) 0.3297(2) 0.5558(2) 0.0274(5) Uani 1 1 d . . . C15 C 0.74262(19) 0.2120(2) 0.5934(2) 0.0416(6) Uani 1 1 d . . . H15A H 0.7852 0.1628 0.5461 0.050 Uiso 1 1 calc R . . H15B H 0.7283 0.1761 0.6678 0.050 Uiso 1 1 calc R . . C16 C 0.47427(17) 0.8514(2) 0.3374(2) 0.0349(6) Uani 1 1 d . . . H16A H 0.4265 0.8053 0.3831 0.052 Uiso 1 1 calc R . . H16B H 0.5177 0.7789 0.3109 0.052 Uiso 1 1 calc R . . H16C H 0.4469 0.8990 0.2706 0.052 Uiso 1 1 calc R . . C17 C 0.45669(15) 1.0730(2) 0.4580(2) 0.0355(6) Uani 1 1 d . . . H17A H 0.4891 1.1436 0.5050 0.053 Uiso 1 1 calc R . . H17B H 0.4107 1.0245 0.5052 0.053 Uiso 1 1 calc R . . H17C H 0.4268 1.1215 0.3933 0.053 Uiso 1 1 calc R . . C18 C 0.47518(16) 0.5913(2) 0.65533(18) 0.0322(5) Uani 1 1 d . . . H18A H 0.4218 0.6541 0.6534 0.048 Uiso 1 1 calc R . . H18B H 0.5179 0.6256 0.7140 0.048 Uiso 1 1 calc R . . H18C H 0.4561 0.4934 0.6741 0.048 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 0.0356(9) 0.0282(8) 0.0194(8) -0.0025(6) 0.0056(6) 0.0082(7) O2 0.0304(8) 0.0251(7) 0.0133(7) -0.0010(6) -0.0044(6) 0.0022(6) O3 0.0171(7) 0.0297(8) 0.0219(8) 0.0021(7) 0.0001(6) -0.0017(6) C1 0.0289(12) 0.0237(11) 0.0276(12) 0.0054(9) 0.0074(9) 0.0048(9) C2 0.0446(14) 0.0319(13) 0.0311(13) 0.0159(10) 0.0126(11) 0.0064(11) C3 0.0361(12) 0.0215(10) 0.0231(11) 0.0076(9) -0.0011(10) 0.0008(9) C4 0.0258(11) 0.0181(10) 0.0234(11) 0.0016(8) -0.0033(9) 0.0010(9) C5 0.0238(10) 0.0163(10) 0.0203(11) -0.0021(8) -0.0007(8) -0.0052(8) C6 0.0190(10) 0.0172(10) 0.0176(10) -0.0017(8) -0.0014(8) -0.0043(8) C7 0.0195(10) 0.0185(9) 0.0136(9) 0.0010(8) -0.0024(8) -0.0014(8) C8 0.0183(10) 0.0228(10) 0.0266(11) 0.0056(9) -0.0034(9) -0.0016(8) C9 0.0259(11) 0.0259(11) 0.0291(12) 0.0051(10) 0.0046(9) 0.0078(9) C10 0.0338(12) 0.0186(9) 0.0245(11) -0.0013(9) 0.0003(10) 0.0047(9) C11 0.0281(11) 0.0181(10) 0.0180(10) 0.0001(8) -0.0057(9) -0.0029(9) C12 0.0163(9) 0.0208(9) 0.0162(10) 0.0026(8) -0.0016(8) -0.0012(8) C13 0.0308(12) 0.0224(11) 0.0202(11) 0.0039(9) -0.0031(10) -0.0043(9) C14 0.0297(11) 0.0204(10) 0.0321(12) 0.0042(10) -0.0045(11) -0.0014(9) C15 0.0508(16) 0.0356(13) 0.0383(14) 0.0106(11) 0.0039(12) 0.0092(12) C16 0.0420(14) 0.0295(12) 0.0333(14) 0.0043(10) -0.0173(11) -0.0039(11) C17 0.0342(13) 0.0305(12) 0.0418(14) 0.0060(11) 0.0042(11) 0.0125(10) C18 0.0254(12) 0.0438(14) 0.0275(13) -0.0004(11) 0.0066(9) -0.0040(10) _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 1.228(2) . ? O2 C7 1.437(2) . ? O2 H2 0.852(9) . ? O3 C18 1.430(2) . ? O3 C12 1.434(2) . ? C1 C6 1.334(3) . ? C1 C2 1.490(3) . ? C1 H1A 0.9500 . ? C2 C3 1.515(3) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C3 C4 1.536(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.522(3) . ? C4 C17 1.524(3) . ? C4 C16 1.538(3) . ? C5 C6 1.486(3) . ? C6 C7 1.528(3) . ? C7 C8 1.544(3) . ? C7 C12 1.561(3) . ? C8 C9 1.539(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.535(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C14 1.508(3) . ? C10 C11 1.533(3) . ? C10 H10A 1.0000 . ? C11 C12 1.532(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.541(3) . ? C13 C14 1.520(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.314(3) . ? C15 H15A 0.9500 . ? C15 H15B 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 C7 O2 H2 105.6(17) . . ? C18 O3 C12 116.83(15) . . ? C6 C1 C2 125.5(2) . . ? C6 C1 H1A 117.3 . . ? C2 C1 H1A 117.3 . . ? C1 C2 C3 113.63(18) . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? H2B C2 H2A 107.7 . . ? C2 C3 C4 112.68(16) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C17 110.60(17) . . ? C5 C4 C16 108.42(16) . . ? C17 C4 C16 110.15(18) . . ? C5 C4 C3 106.79(16) . . ? C17 C4 C3 109.20(16) . . ? C16 C4 C3 111.63(18) . . ? O1 C5 C6 121.99(18) . . ? O1 C5 C4 120.54(18) . . ? C6 C5 C4 117.41(17) . . ? C1 C6 C5 117.94(17) . . ? C1 C6 C7 122.92(18) . . ? C5 C6 C7 119.14(16) . . ? O2 C7 C6 109.44(15) . . ? O2 C7 C8 104.09(15) . . ? C6 C7 C8 114.51(16) . . ? O2 C7 C12 110.20(15) . . ? C6 C7 C12 109.57(15) . . ? C8 C7 C12 108.89(14) . . ? C9 C8 C7 116.81(16) . . ? C9 C8 H8A 108.1 . . ? C7 C8 H8A 108.1 . . ? C9 C8 H8B 108.1 . . ? C7 C8 H8B 108.1 . . ? H8A C8 H8B 107.3 . . ? C10 C9 C8 110.79(17) . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C14 C10 C11 101.82(16) . . ? C14 C10 C9 110.51(18) . . ? C11 C10 C9 108.56(15) . . ? C14 C10 H10A 111.8 . . ? C11 C10 H10A 111.8 . . ? C9 C10 H10A 111.8 . . ? C10 C11 C12 101.61(15) . . ? C10 C11 H11A 111.4 . . ? C12 C11 H11A 111.4 . . ? C10 C11 H11B 111.4 . . ? C12 C11 H11B 111.4 . . ? H11A C11 H11B 109.3 . . ? O3 C12 C11 108.21(15) . . ? O3 C12 C13 114.73(15) . . ? C11 C12 C13 101.78(15) . . ? O3 C12 C7 109.91(14) . . ? C11 C12 C7 109.92(15) . . ? C13 C12 C7 111.89(15) . . ? C14 C13 C12 104.44(17) . . ? C14 C13 H13A 110.9 . . ? C12 C13 H13A 110.9 . . ? C14 C13 H13B 110.9 . . ? C12 C13 H13B 110.9 . . ? H13A C13 H13B 108.9 . . ? C15 C14 C10 126.5(2) . . ? C15 C14 C13 125.3(2) . . ? C10 C14 C13 108.16(16) . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? C4 C16 H16A 109.5 . . ? C4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C4 C17 H17A 109.5 . . ? C4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C6 C1 C2 C3 11.7(3) . . . . ? C1 C2 C3 C4 -39.6(3) . . . . ? C2 C3 C4 C5 56.7(2) . . . . ? C2 C3 C4 C17 176.27(19) . . . . ? C2 C3 C4 C16 -61.7(2) . . . . ? C17 C4 C5 O1 9.2(3) . . . . ? C16 C4 C5 O1 -111.6(2) . . . . ? C3 C4 C5 O1 127.9(2) . . . . ? C17 C4 C5 C6 -168.01(17) . . . . ? C16 C4 C5 C6 71.1(2) . . . . ? C3 C4 C5 C6 -49.3(2) . . . . ? C2 C1 C6 C5 -3.2(3) . . . . ? C2 C1 C6 C7 175.7(2) . . . . ? O1 C5 C6 C1 -153.5(2) . . . . ? C4 C5 C6 C1 23.7(3) . . . . ? O1 C5 C6 C7 27.6(3) . . . . ? C4 C5 C6 C7 -155.23(17) . . . . ? C1 C6 C7 O2 136.55(19) . . . . ? C5 C6 C7 O2 -44.6(2) . . . . ? C1 C6 C7 C8 20.1(3) . . . . ? C5 C6 C7 C8 -161.02(17) . . . . ? C1 C6 C7 C12 -102.5(2) . . . . ? C5 C6 C7 C12 76.3(2) . . . . ? O2 C7 C8 C9 158.14(16) . . . . ? C6 C7 C8 C9 -82.4(2) . . . . ? C12 C7 C8 C9 40.6(2) . . . . ? C7 C8 C9 C10 -42.1(2) . . . . ? C8 C9 C10 C14 -52.6(2) . . . . ? C8 C9 C10 C11 58.3(2) . . . . ? C14 C10 C11 C12 43.69(18) . . . . ? C9 C10 C11 C12 -72.91(19) . . . . ? C18 O3 C12 C11 150.42(17) . . . . ? C18 O3 C12 C13 37.6(2) . . . . ? C18 O3 C12 C7 -89.54(19) . . . . ? C10 C11 C12 O3 -166.91(14) . . . . ? C10 C11 C12 C13 -45.68(18) . . . . ? C10 C11 C12 C7 73.05(17) . . . . ? O2 C7 C12 O3 70.43(18) . . . . ? C6 C7 C12 O3 -50.0(2) . . . . ? C8 C7 C12 O3 -175.98(15) . . . . ? O2 C7 C12 C11 -170.57(15) . . . . ? C6 C7 C12 C11 68.96(19) . . . . ? C8 C7 C12 C11 -57.0(2) . . . . ? O2 C7 C12 C13 -58.3(2) . . . . ? C6 C7 C12 C13 -178.73(16) . . . . ? C8 C7 C12 C13 55.3(2) . . . . ? O3 C12 C13 C14 146.44(16) . . . . ? C11 C12 C13 C14 29.85(19) . . . . ? C7 C12 C13 C14 -87.47(19) . . . . ? C11 C10 C14 C15 153.1(2) . . . . ? C9 C10 C14 C15 -91.8(3) . . . . ? C11 C10 C14 C13 -25.2(2) . . . . ? C9 C10 C14 C13 89.94(19) . . . . ? C12 C13 C14 C15 178.8(2) . . . . ? C12 C13 C14 C10 -2.9(2) . . . . ? 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 O2 H2 O1 0.852(9) 1.872(14) 2.658(2) 153(2) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.196 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.039