data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Edwin Weber' _publ_contact_author_address ; Institut fur Organische Chemie Universitat Bergakademie Freiberg Leipziger Str 29 Freiberg/Sachsen D-09596 GERMANY ; _publ_contact_author_email EDWIN.WEBER@CHEMIE.TU-FREIBERG.DE _publ_section_title ; Oligofunctional amphiphiles featuring geometric core group preorganization: synthesis and study of Langmuir and Langmuir-Blodgett films ; loop_ _publ_author_name 'Edwin Weber' 'Petra U. Muller' 'Gerd Rheinwald' 'Wihelm Seichter' data_m126cory _database_code_depnum_ccdc_archive 'CCDC 278011' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H34 O8 S2' _chemical_formula_weight 610.71 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3831(8) _cell_length_b 9.6997(9) _cell_length_c 10.2470(9) _cell_angle_alpha 117.460(2) _cell_angle_beta 95.4470(10) _cell_angle_gamma 106.7540(10) _cell_volume 763.39(12) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plateless _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8771 _exptl_absorpt_correction_T_max 0.9911 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5642 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0928 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 30.40 _reflns_number_total 3717 _reflns_number_gt 2164 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINT _computing_data_reduction ABSEN _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ZORTEP _computing_publication_material SHELX-97 _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 w=1/[\s^2^(Fo^2^)+(0.0677P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3717 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1246 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1297 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.97517(9) 0.70762(11) 0.32190(9) 0.0380(2) Uani 1 d . . . O1 O 0.6545(3) 0.8936(3) 0.4740(3) 0.0446(6) Uani 1 d . . . H1 H 0.7157 0.8505 0.4324 0.067 Uiso 1 calc R . . O2 O 0.7722(2) 0.5123(3) 0.6392(2) 0.0423(6) Uani 1 d . . . O3 O 0.6183(2) 0.5051(3) 0.7921(2) 0.0374(5) Uani 1 d . . . O4 O 0.8450(3) 0.7691(3) 0.3233(2) 0.0449(6) Uani 1 d . . . C1 C 0.6102(3) 0.8384(4) 0.5693(3) 0.0302(6) Uani 1 d . . . C2 C 0.6622(3) 0.7278(4) 0.5883(3) 0.0287(6) Uani 1 d . . . H2 H 0.7306 0.6870 0.5325 0.034 Uiso 1 calc R . . C3 C 0.6162(3) 0.6758(3) 0.6874(3) 0.0263(6) Uani 1 d . . . C4 C 0.5154(3) 0.7338(3) 0.7694(3) 0.0272(6) Uani 1 d . . . H4 H 0.4845 0.6995 0.8387 0.033 Uiso 1 calc R . . C5 C 0.4604(3) 0.8435(3) 0.7481(3) 0.0256(6) Uani 1 d . . . C6 C 0.5081(3) 0.8964(4) 0.6493(3) 0.0296(6) Uani 1 d . . . H6 H 0.4714 0.9720 0.6362 0.036 Uiso 1 calc R . . C7 C 0.6782(3) 0.5575(4) 0.7026(3) 0.0318(7) Uani 1 d . . . C8 C 0.6733(4) 0.3885(4) 0.8113(4) 0.0435(8) Uani 1 d . . . H8A H 0.7854 0.4426 0.8627 0.052 Uiso 1 calc R . . H8B H 0.6555 0.2888 0.7107 0.052 Uiso 1 calc R . . C9 C 0.5848(4) 0.3384(4) 0.9067(4) 0.0481(9) Uani 1 d . . . H9A H 0.6188 0.2593 0.9223 0.072 Uiso 1 calc R . . H9B H 0.4742 0.2850 0.8545 0.072 Uiso 1 calc R . . H9C H 0.6034 0.4381 1.0058 0.072 Uiso 1 calc R . . C10 C 0.3493(3) 0.8976(3) 0.8267(3) 0.0271(6) Uani 1 d . . . C11 C 0.2515(3) 0.9334(4) 0.8835(3) 0.0301(6) Uani 1 d . . . C12 C 0.1254(3) 0.9693(3) 0.9451(3) 0.0270(6) Uani 1 d . . . C13 C 0.0646(3) 0.9038(4) 1.0321(3) 0.0318(7) Uani 1 d . . . H13 H 0.1087 0.8376 1.0541 0.038 Uiso 1 calc R . . C14 C -0.0592(3) 0.9336(4) 1.0869(3) 0.0324(7) Uani 1 d . . . H14 H -0.0994 0.8881 1.1463 0.039 Uiso 1 calc R . . C15 C 0.8891(4) 0.4950(4) 0.2722(4) 0.0529(10) Uani 1 d . . . H15A H 0.8279 0.4269 0.1654 0.079 Uiso 1 calc R . . H15B H 0.8218 0.4868 0.3380 0.079 Uiso 1 calc R . . H15C H 0.9701 0.4541 0.2860 0.079 Uiso 1 calc R . . C16 C 1.0720(4) 0.7876(4) 0.5143(3) 0.0440(8) Uani 1 d . . . H16A H 1.1291 0.9087 0.5641 0.066 Uiso 1 calc R . . H16B H 1.1442 0.7326 0.5164 0.066 Uiso 1 calc R . . H16C H 0.9961 0.7655 0.5686 0.066 Uiso 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 S1 0.0388(4) 0.0483(5) 0.0421(5) 0.0267(4) 0.0216(3) 0.0269(4) O1 0.0553(14) 0.0653(16) 0.0603(14) 0.0508(13) 0.0417(12) 0.0441(13) O2 0.0441(13) 0.0569(15) 0.0564(14) 0.0382(12) 0.0292(11) 0.0383(12) O3 0.0444(12) 0.0494(14) 0.0480(13) 0.0362(11) 0.0255(10) 0.0331(11) O4 0.0534(14) 0.0636(16) 0.0536(14) 0.0411(12) 0.0334(11) 0.0439(13) C1 0.0316(15) 0.0355(17) 0.0335(15) 0.0213(13) 0.0148(12) 0.0176(14) C2 0.0270(14) 0.0382(17) 0.0322(15) 0.0208(14) 0.0156(12) 0.0201(14) C3 0.0246(14) 0.0289(16) 0.0305(15) 0.0167(12) 0.0104(11) 0.0131(12) C4 0.0260(14) 0.0315(16) 0.0288(14) 0.0168(13) 0.0121(11) 0.0134(13) C5 0.0245(14) 0.0267(15) 0.0277(14) 0.0124(12) 0.0110(11) 0.0137(13) C6 0.0307(15) 0.0330(17) 0.0366(16) 0.0209(14) 0.0157(12) 0.0197(14) C7 0.0308(15) 0.0378(18) 0.0380(16) 0.0227(14) 0.0151(13) 0.0201(14) C8 0.052(2) 0.056(2) 0.056(2) 0.0412(18) 0.0260(16) 0.0393(19) C9 0.066(2) 0.052(2) 0.049(2) 0.0349(18) 0.0224(17) 0.034(2) C10 0.0305(15) 0.0284(16) 0.0282(14) 0.0161(13) 0.0105(11) 0.0155(13) C11 0.0348(16) 0.0295(16) 0.0298(15) 0.0148(13) 0.0115(12) 0.0169(14) C12 0.0310(15) 0.0299(16) 0.0249(14) 0.0122(12) 0.0138(11) 0.0189(14) C13 0.0383(17) 0.0352(18) 0.0357(16) 0.0211(14) 0.0182(13) 0.0245(15) C14 0.0395(17) 0.0394(18) 0.0357(16) 0.0237(14) 0.0242(13) 0.0254(15) C15 0.0382(19) 0.033(2) 0.066(2) 0.0109(17) 0.0025(16) 0.0146(16) C16 0.0408(19) 0.044(2) 0.0428(19) 0.0194(16) 0.0116(14) 0.0148(16) _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 S1 O4 1.505(2) 1 ? S1 O4 1.505(2) . ? S1 C15 1.777(3) . ? S1 C16 1.777(3) . ? O1 C1 1.358(3) . ? O1 H1 0.8400 . ? O2 C7 1.209(3) . ? O3 C7 1.333(3) . ? O3 C8 1.451(3) . ? O4 O4 0.000(13) 1 ? C1 C2 1.380(4) . ? C1 C6 1.393(3) . ? C2 C3 1.379(4) . ? C2 H2 0.9500 . ? C3 C4 1.392(3) . ? C3 C7 1.487(4) . ? C4 C5 1.398(4) . ? C4 H4 0.9500 . ? C5 C6 1.386(4) . ? C5 C10 1.449(3) . ? C6 H6 0.9500 . ? C8 C9 1.498(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.183(4) . ? C11 C12 1.448(4) . ? C12 C13 1.390(4) . ? C12 C14 1.402(4) 2_577 ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 C12 1.402(4) 2_577 ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 O4 S1 O4 0.0(4) 1 . ? O4 S1 C15 106.11(15) 1 . ? O4 S1 C15 106.11(15) . . ? O4 S1 C16 107.93(14) 1 . ? O4 S1 C16 107.93(14) . . ? C15 S1 C16 96.61(16) . . ? C1 O1 H1 109.5 . . ? C7 O3 C8 116.0(2) . . ? O4 O4 S1 0(10) 1 . ? O1 C1 C2 122.3(2) . . ? O1 C1 C6 118.0(2) . . ? C2 C1 C6 119.7(3) . . ? C1 C2 C3 120.8(2) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C2 C3 C4 120.3(2) . . ? C2 C3 C7 117.6(2) . . ? C4 C3 C7 122.1(2) . . ? C3 C4 C5 119.0(2) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 120.5(2) . . ? C6 C5 C10 120.1(2) . . ? C4 C5 C10 119.4(2) . . ? C5 C6 C1 119.8(2) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O2 C7 O3 123.5(3) . . ? O2 C7 C3 123.4(3) . . ? O3 C7 C3 113.1(2) . . ? O3 C8 C9 107.0(2) . . ? O3 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? O3 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C5 176.0(3) . . ? C10 C11 C12 176.8(3) . . ? C13 C12 C14 119.0(2) . 2_577 ? C13 C12 C11 120.8(2) . . ? C14 C12 C11 120.1(2) 2_577 . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C12 120.1(3) . 2_577 ? C13 C14 H14 120.0 . . ? C12 C14 H14 120.0 2_577 . ? S1 C15 H15A 109.5 . . ? S1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S1 C16 H16A 109.5 . . ? S1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 O1 H1 O4 0.84 1.83 2.662(3) 171.5 1 C6 H6 O1 0.95 2.52 3.446(3) 164.1 2_676 C15 H15C O2 0.98 2.35 3.251(4) 153.3 2_766 C16 H16B O2 0.98 2.57 3.426(4) 145.7 2_766 _diffrn_measured_fraction_theta_max 0.806 _diffrn_reflns_theta_full 30.40 _diffrn_measured_fraction_theta_full 0.806 _refine_diff_density_max 0.309 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.061 data_5a _database_code_depnum_ccdc_archive 'CCDC 278012' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H70 O6' _chemical_formula_weight 791.08 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8583(5) _cell_length_b 9.1667(5) _cell_length_c 15.4654(4) _cell_angle_alpha 88.4100(10) _cell_angle_beta 80.604(3) _cell_angle_gamma 65.605(3) _cell_volume 1127.25(9) _cell_formula_units_Z 1 _cell_measurement_temperature 93(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 0.61 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 430 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type 'multi scans' _exptl_absorpt_correction_T_min 0.9561 _exptl_absorpt_correction_T_max 0.9924 _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(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 6717 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 28.41 _reflns_number_total 6463 _reflns_number_gt 4243 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _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 w=1/[\s^2^(Fo^2^)+(0.0917P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6463 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1551 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.33534(17) 0.48054(16) 0.30569(9) 0.0179(3) Uani 1 d . . . C2 C 0.47892(17) 0.33869(16) 0.30535(9) 0.0170(3) Uani 1 d . . . H2 H 0.5865 0.3330 0.2800 0.020 Uiso 1 calc R . . C3 C 0.46166(17) 0.20487(16) 0.34307(9) 0.0174(3) Uani 1 d . . . C4 C 0.30615(17) 0.21003(17) 0.38023(9) 0.0192(3) Uani 1 d . . . H4 H 0.2974 0.1178 0.4058 0.023 Uiso 1 calc R . . C5 C 0.16223(16) 0.35220(17) 0.37968(9) 0.0183(3) Uani 1 d . . . C6 C 0.17898(17) 0.48619(17) 0.34238(9) 0.0190(3) Uani 1 d . . . H6 H 0.0815 0.5832 0.3421 0.023 Uiso 1 calc R . . C7 C 0.48955(17) 0.62607(17) 0.23327(10) 0.0206(3) Uani 1 d . . . H7A H 0.5437 0.5495 0.1820 0.025 Uiso 1 calc R . . H7B H 0.5672 0.5982 0.2764 0.025 Uiso 1 calc R . . C8 C 0.44658(17) 0.79605(17) 0.20526(10) 0.0218(3) Uani 1 d . . . H8A H 0.3979 0.8697 0.2579 0.026 Uiso 1 calc R . . H8B H 0.3600 0.8249 0.1670 0.026 Uiso 1 calc R . . C9 C 0.59832(17) 0.81961(17) 0.15630(10) 0.0217(3) Uani 1 d . . . H9A H 0.6824 0.7968 0.1956 0.026 Uiso 1 calc R . . H9B H 0.6507 0.7422 0.1053 0.026 Uiso 1 calc R . . C10 C 0.55106(17) 0.98916(16) 0.12441(10) 0.0208(3) Uani 1 d . . . H10A H 0.4975 1.0660 0.1756 0.025 Uiso 1 calc R . . H10B H 0.4670 1.0113 0.0852 0.025 Uiso 1 calc R . . C11 C 0.69957(18) 1.01789(17) 0.07553(10) 0.0217(3) Uani 1 d . . . H11A H 0.7524 0.9421 0.0239 0.026 Uiso 1 calc R . . H11B H 0.7842 0.9950 0.1145 0.026 Uiso 1 calc R . . C12 C 0.65062(17) 1.18841(16) 0.04487(10) 0.0213(3) Uani 1 d . . . H12A H 0.6025 1.2638 0.0968 0.026 Uiso 1 calc R . . H12B H 0.5620 1.2130 0.0082 0.026 Uiso 1 calc R . . C13 C 0.79774(17) 1.21602(16) -0.00786(10) 0.0207(3) Uani 1 d . . . H13A H 0.8873 1.1890 0.0284 0.025 Uiso 1 calc R . . H13B H 0.8442 1.1420 -0.0604 0.025 Uiso 1 calc R . . C14 C 0.75070(17) 1.38713(16) -0.03720(10) 0.0202(3) Uani 1 d . . . H14A H 0.6619 1.4141 -0.0739 0.024 Uiso 1 calc R . . H14B H 0.7037 1.4614 0.0152 0.024 Uiso 1 calc R . . C15 C 0.89888(17) 1.41269(17) -0.08907(10) 0.0213(3) Uani 1 d . . . H15A H 0.9899 1.3799 -0.0534 0.026 Uiso 1 calc R . . H15B H 0.9421 1.3420 -0.1429 0.026 Uiso 1 calc R . . C16 C 0.85698(17) 1.58477(17) -0.11517(10) 0.0207(3) Uani 1 d . . . H16A H 0.8124 1.6560 -0.0616 0.025 Uiso 1 calc R . . H16B H 0.7676 1.6173 -0.1519 0.025 Uiso 1 calc R . . C17 C 1.00801(18) 1.60759(18) -0.16566(10) 0.0237(3) Uani 1 d . . . H17A H 1.0974 1.5749 -0.1290 0.028 Uiso 1 calc R . . H17B H 1.0526 1.5363 -0.2192 0.028 Uiso 1 calc R . . C18 C 0.9668(2) 1.77952(18) -0.19189(11) 0.0289(4) Uani 1 d . . . H18A H 0.8825 1.8110 -0.2308 0.043 Uiso 1 calc R . . H18B H 1.0690 1.7871 -0.2226 0.043 Uiso 1 calc R . . H18C H 0.9222 1.8511 -0.1392 0.043 Uiso 1 calc R . . C19 C 0.61225(17) 0.05195(17) 0.34613(10) 0.0208(3) Uani 1 d . . . C20 C 0.91143(17) -0.07850(17) 0.30826(10) 0.0250(4) Uani 1 d . . . H20A H 0.9947 -0.0840 0.2559 0.030 Uiso 1 calc R . . H20B H 0.8921 -0.1774 0.3078 0.030 Uiso 1 calc R . . C21 C 0.97888(19) -0.06764(19) 0.38993(11) 0.0323(4) Uani 1 d . . . H21A H 0.9878 0.0351 0.3930 0.048 Uiso 1 calc R . . H21B H 1.0902 -0.1557 0.3883 0.048 Uiso 1 calc R . . H21C H 0.9025 -0.0752 0.4416 0.048 Uiso 1 calc R . . C22 C -0.00476(17) 0.36848(17) 0.41562(9) 0.0196(3) Uani 1 d . . . C23 C -0.15003(17) 0.39929(16) 0.44145(9) 0.0195(3) Uani 1 d . . . C24 C -0.32662(17) 0.44859(17) 0.47124(9) 0.0176(3) Uani 1 d . . . C25 C -0.43730(17) 0.60748(17) 0.46264(9) 0.0187(3) Uani 1 d . . . H25 H -0.3946 0.6812 0.4372 0.022 Uiso 1 calc R . . C26 C -0.39223(17) 0.34154(17) 0.50932(9) 0.0190(3) Uani 1 d . . . H26 H -0.3186 0.2332 0.5158 0.023 Uiso 1 calc R . . O1 O 0.33281(12) 0.62086(12) 0.27203(7) 0.0228(3) Uani 1 d . . . O2 O 0.75434(12) 0.06080(12) 0.30516(7) 0.0239(3) Uani 1 d . . . O3 O 0.60825(13) -0.06645(13) 0.37966(8) 0.0339(3) Uani 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 C1 0.0191(7) 0.0171(7) 0.0178(7) 0.0026(5) -0.0025(6) -0.0083(6) C2 0.0153(7) 0.0207(7) 0.0153(7) 0.0017(5) -0.0003(5) -0.0086(6) C3 0.0165(7) 0.0171(7) 0.0183(7) -0.0005(5) -0.0031(5) -0.0064(6) C4 0.0183(7) 0.0193(7) 0.0213(8) 0.0020(6) -0.0017(6) -0.0098(6) C5 0.0145(7) 0.0220(7) 0.0188(7) -0.0011(6) -0.0012(6) -0.0085(6) C6 0.0149(7) 0.0174(7) 0.0230(8) 0.0007(6) -0.0030(6) -0.0050(6) C7 0.0165(7) 0.0206(7) 0.0236(8) 0.0039(6) -0.0008(6) -0.0078(6) C8 0.0207(7) 0.0175(7) 0.0262(8) 0.0056(6) -0.0021(6) -0.0079(6) C9 0.0211(7) 0.0191(7) 0.0252(8) 0.0042(6) -0.0032(6) -0.0089(6) C10 0.0216(7) 0.0179(7) 0.0236(8) 0.0039(6) -0.0034(6) -0.0091(6) C11 0.0210(7) 0.0194(7) 0.0252(8) 0.0059(6) -0.0037(6) -0.0093(6) C12 0.0224(7) 0.0183(7) 0.0241(8) 0.0039(6) -0.0023(6) -0.0099(6) C13 0.0190(7) 0.0189(7) 0.0249(8) 0.0052(6) -0.0023(6) -0.0092(6) C14 0.0193(7) 0.0182(7) 0.0236(8) 0.0034(6) -0.0031(6) -0.0086(6) C15 0.0205(7) 0.0204(8) 0.0240(8) 0.0041(6) -0.0014(6) -0.0104(6) C16 0.0222(7) 0.0193(7) 0.0216(8) 0.0036(6) -0.0036(6) -0.0100(6) C17 0.0228(8) 0.0237(8) 0.0274(8) 0.0059(6) -0.0034(6) -0.0130(6) C18 0.0333(9) 0.0270(8) 0.0308(9) 0.0075(7) -0.0031(7) -0.0179(7) C19 0.0191(7) 0.0186(7) 0.0246(8) 0.0028(6) -0.0037(6) -0.0079(6) C20 0.0155(7) 0.0171(7) 0.0343(9) 0.0033(6) -0.0010(6) 0.0001(6) C21 0.0250(8) 0.0249(8) 0.0401(10) -0.0010(7) -0.0096(7) -0.0019(7) C22 0.0196(7) 0.0177(7) 0.0227(8) 0.0011(6) -0.0038(6) -0.0089(6) C23 0.0186(7) 0.0180(7) 0.0232(8) 0.0003(6) -0.0030(6) -0.0090(6) C24 0.0151(7) 0.0213(7) 0.0182(7) 0.0002(6) -0.0012(5) -0.0098(6) C25 0.0200(7) 0.0195(7) 0.0203(8) 0.0032(6) -0.0022(6) -0.0124(6) C26 0.0174(7) 0.0172(7) 0.0222(8) 0.0027(6) -0.0043(6) -0.0069(6) O1 0.0161(5) 0.0175(5) 0.0326(6) 0.0076(4) 0.0001(4) -0.0066(4) O2 0.0140(5) 0.0180(5) 0.0342(6) 0.0058(4) -0.0020(4) -0.0023(4) O3 0.0253(6) 0.0208(6) 0.0519(8) 0.0126(5) -0.0020(5) -0.0081(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 C1 O1 1.3671(16) . ? C1 C6 1.3888(19) . ? C1 C2 1.3931(19) . ? C2 C3 1.3980(19) . ? C2 H2 0.9500 . ? C3 C4 1.3854(19) . ? C3 C19 1.4896(19) . ? C4 C5 1.3980(19) . ? C4 H4 0.9500 . ? C5 C6 1.3953(19) . ? C5 C22 1.4398(19) . ? C6 H6 0.9500 . ? C7 O1 1.4391(16) . ? C7 C8 1.5122(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5248(19) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5236(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5238(19) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5239(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5302(19) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.5239(19) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.5236(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.5228(19) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5246(19) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.523(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O3 1.2012(17) . ? C19 O2 1.3466(17) . ? C20 O2 1.4559(16) . ? C20 C21 1.505(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.1973(19) . ? C23 C24 1.4338(18) . ? C24 C25 1.3973(19) . ? C24 C26 1.4053(19) . ? C25 C26 1.3788(19) 2_466 ? C25 H25 0.9500 . ? C26 C25 1.3788(19) 2_466 ? C26 H26 0.9500 . ? 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 O1 C1 C6 114.89(11) . . ? O1 C1 C2 125.28(12) . . ? C6 C1 C2 119.83(13) . . ? C1 C2 C3 118.71(12) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 121.72(12) . . ? C4 C3 C19 117.75(12) . . ? C2 C3 C19 120.51(12) . . ? C3 C4 C5 119.36(13) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 119.09(12) . . ? C6 C5 C22 117.54(12) . . ? C4 C5 C22 123.37(13) . . ? C1 C6 C5 121.28(12) . . ? C1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? O1 C7 C8 106.12(10) . . ? O1 C7 H7A 110.5 . . ? C8 C7 H7A 110.5 . . ? O1 C7 H7B 110.5 . . ? C8 C7 H7B 110.5 . . ? H7A C7 H7B 108.7 . . ? C7 C8 C9 112.99(11) . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 112.25(11) . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C9 C10 C11 113.88(11) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 113.27(11) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 113.54(11) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 113.91(11) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 113.19(11) . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C13 C14 H14B 108.9 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 114.17(11) . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 113.10(11) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 113.31(12) . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 O2 123.64(13) . . ? O3 C19 C3 124.45(13) . . ? O2 C19 C3 111.89(12) . . ? O2 C20 C21 110.13(12) . . ? O2 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? O2 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C5 172.37(15) . . ? C22 C23 C24 175.69(15) . . ? C25 C24 C26 118.74(12) . . ? C25 C24 C23 119.41(12) . . ? C26 C24 C23 121.85(13) . . ? C26 C25 C24 120.75(12) 2_466 . ? C26 C25 H25 119.6 2_466 . ? C24 C25 H25 119.6 . . ? C25 C26 C24 120.51(13) 2_466 . ? C25 C26 H26 119.7 2_466 . ? C24 C26 H26 119.7 . . ? C1 O1 C7 118.60(10) . . ? C19 O2 C20 116.96(11) . . ? 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 C18 H18B O2 0.98 2.66 3.5701(18) 154.7 2_775 C25 H25 O3 0.95 2.46 3.3701(17) 159.6 1_465 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.419 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.047 data_pemu5e _database_code_depnum_ccdc_archive 'CCDC 278014' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 O3' _chemical_formula_weight 190.19 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)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.720(5) _cell_length_b 12.944(9) _cell_length_c 8.918(5) _cell_angle_alpha 90.00(2) _cell_angle_beta 100.47(4) _cell_angle_gamma 90.00(3) _cell_volume 989.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.13 _cell_measurement_theta_max 24.69 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.771 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8017 _exptl_absorpt_correction_T_max 0.8611 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD4 (Enraf Nonius)' _diffrn_measurement_method 'omega-2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 250 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% ? _diffrn_reflns_number 1800 _diffrn_reflns_av_R_equivalents 0.0878 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.04 _diffrn_reflns_theta_max 65.01 _reflns_number_total 1681 _reflns_number_gt 1271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 software' _computing_cell_refinement 'CAD4 software' _computing_data_reduction Helena _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material PLATON _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 w=1/[\s^2^(Fo^2^)+(0.1145P)^2^+0.1021P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1681 _refine_ls_number_parameters 132 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0814 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1744 _refine_ls_wR_factor_gt 0.1554 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.004 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5131(2) 0.36373(12) 0.7412(2) 0.0756(6) Uani 1 d . . . H1 H 0.4504 0.3977 0.6812 0.113 Uiso 1 calc R . . O2 O 0.1862(2) -0.01306(12) 0.4517(2) 0.0670(6) Uani 1 d . . . O3 O 0.13420(18) 0.15206(12) 0.38720(18) 0.0619(5) Uani 1 d . . . C1 C 0.4840(2) 0.26129(17) 0.7161(2) 0.0536(6) Uani 1 d . . . C2 C 0.3649(3) 0.22543(16) 0.6049(2) 0.0513(6) Uani 1 d . . . H2 H 0.3002 0.2714 0.5429 0.062 Uiso 1 calc R . . C3 C 0.3431(2) 0.11920(16) 0.5869(2) 0.0489(6) Uani 1 d . . . C4 C 0.4369(3) 0.05023(18) 0.6782(3) 0.0535(6) Uani 1 d . . . H4 H 0.4209 -0.0204 0.6646 0.064 Uiso 1 calc R . . C5 C 0.5565(3) 0.08687(18) 0.7913(3) 0.0527(6) Uani 1 d . . . C6 C 0.5797(3) 0.19303(18) 0.8072(3) 0.0565(6) Uani 1 d . . . H6 H 0.6608 0.2181 0.8805 0.068 Uiso 1 calc R . . C7 C 0.2138(3) 0.07822(17) 0.4694(2) 0.0517(6) Uani 1 d . . . C8 C 0.0051(3) 0.1221(2) 0.2688(3) 0.0651(7) Uani 1 d . . . H8A H -0.0752 0.0880 0.3130 0.078 Uiso 1 calc R . . H8B H 0.0404 0.0750 0.1976 0.078 Uiso 1 calc R . . C9 C -0.0566(3) 0.2181(2) 0.1898(3) 0.0898(10) Uani 1 d . . . H9A H -0.1427 0.2015 0.1100 0.135 Uiso 1 calc R . . H9B H 0.0240 0.2510 0.1468 0.135 Uiso 1 calc R . . H9C H -0.0912 0.2639 0.2614 0.135 Uiso 1 calc R . . C10 C 0.6551(3) 0.01760(19) 0.8943(3) 0.0616(7) Uani 1 d . . . C11 C 0.7356(4) -0.0329(2) 0.9826(4) 0.0784(9) Uani 1 d D . . H11 H 0.804(3) -0.069(3) 1.056(3) 0.121(12) Uiso 1 d 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 0.0790(12) 0.0403(10) 0.0887(13) -0.0028(8) -0.0345(10) 0.0007(8) O2 0.0706(11) 0.0452(10) 0.0737(12) -0.0019(8) -0.0175(9) -0.0052(8) O3 0.0637(10) 0.0489(9) 0.0619(10) 0.0032(7) -0.0186(8) -0.0017(8) C1 0.0553(14) 0.0411(12) 0.0583(13) -0.0022(10) -0.0064(11) 0.0006(10) C2 0.0529(13) 0.0435(12) 0.0515(12) 0.0020(10) -0.0064(10) 0.0032(10) C3 0.0515(12) 0.0445(12) 0.0468(12) 0.0008(9) -0.0015(10) 0.0008(9) C4 0.0567(14) 0.0440(12) 0.0556(14) 0.0019(10) -0.0009(11) 0.0019(10) C5 0.0530(13) 0.0494(13) 0.0520(13) 0.0041(10) -0.0002(10) 0.0051(10) C6 0.0548(13) 0.0515(13) 0.0547(14) -0.0011(10) -0.0124(11) 0.0012(11) C7 0.0531(13) 0.0454(12) 0.0528(13) 0.0024(10) -0.0007(11) -0.0005(10) C8 0.0608(15) 0.0649(16) 0.0591(14) 0.0007(12) -0.0168(12) -0.0036(12) C9 0.091(2) 0.082(2) 0.0805(19) 0.0107(15) -0.0275(17) 0.0070(16) C10 0.0647(15) 0.0526(14) 0.0602(15) 0.0029(11) -0.0083(12) 0.0012(11) C11 0.0824(19) 0.0606(17) 0.0793(19) 0.0072(14) -0.0197(16) 0.0105(14) _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 1.361(3) . ? O1 H1 0.8200 . ? O2 C7 1.210(3) . ? O3 C7 1.322(3) . ? O3 C8 1.450(3) . ? C1 C6 1.375(3) . ? C1 C2 1.379(3) . ? C2 C3 1.393(3) . ? C2 H2 0.9300 . ? C3 C4 1.374(3) . ? C3 C7 1.490(3) . ? C4 C5 1.396(3) . ? C4 H4 0.9300 . ? C5 C6 1.392(4) . ? C5 C10 1.449(3) . ? C6 H6 0.9300 . ? C8 C9 1.480(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.157(4) . ? C11 H11 0.929(18) . ? 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 O1 H1 109.5 . . ? C7 O3 C8 118.08(19) . . ? O1 C1 C6 117.0(2) . . ? O1 C1 C2 122.7(2) . . ? C6 C1 C2 120.4(2) . . ? C1 C2 C3 118.95(19) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 121.3(2) . . ? C4 C3 C7 118.6(2) . . ? C2 C3 C7 120.14(19) . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 119.0(2) . . ? C6 C5 C10 119.2(2) . . ? C4 C5 C10 121.8(2) . . ? C1 C6 C5 120.8(2) . . ? C1 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? O2 C7 O3 124.1(2) . . ? O2 C7 C3 123.1(2) . . ? O3 C7 C3 112.74(19) . . ? O3 C8 C9 106.8(2) . . ? O3 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? O3 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C5 175.9(3) . . ? C10 C11 H11 176(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 C11 H11 O1 0.929(18) 2.35(2) 3.271(4) 172(3) 2_647 O1 H1 O2 0.82 1.91 2.727(3) 175.2 2_556 _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 65.01 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.289 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.078