# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Michel Miesch' _publ_contact_author_address ;Universite de Strasbourg - Institut de Chimie - UMR 7177 Laboratoire de Chimie Organique Synthetique 1 rue Blaise Pascal BP 296/R8 67008 Strasbourg France ; _publ_contact_author_email m.miesch@unistra.fr _publ_contact_author_phone +33368851752 _publ_contact_author_fax +33368851754 loop_ _publ_author_name _publ_author_address C.Schafer ;Universite de Strasbourg - Institut de Chimie - UMR 7177 Laboratoire de Chimie Organique Synthetique 1 rue Blaise Pascal BP 296/R8 67008 Strasbourg France ; M.Miesch ;Universite de Strasbourg - Institut de Chimie - UMR 7177 Laboratoire de Chimie Organique Synthetique 1 rue Blaise Pascal BP 296/R8 67008 Strasbourg France ; L.Miesch] ;Universite de Strasbourg - Institut de Chimie - UMR 7177 Laboratoire de Chimie Organique Synthetique 1 rue Blaise Pascal BP 296/R8 67008 Strasbourg France ; data_mmlm100331 _database_code_depnum_ccdc_archive 'CCDC 784204' #TrackingRef '01 cs lm mm 5 6 cis.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 O3' _chemical_formula_sum 'C14 H22 O3' _chemical_formula_weight 238.32 _chemical_absolute_configuration rm 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 0.0000 '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 0.0000 '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_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.0156(2) _cell_length_b 8.4956(4) _cell_length_c 19.4087(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1321.68(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12240 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 KappaCCD _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 11661 _diffrn_reflns_av_R_equivalents 0.1199 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1758 _reflns_number_gt 1516 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0990P)^2^+0.7852P] 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 -10(10) _refine_ls_number_reflns 1758 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.1940 _refine_ls_wR_factor_gt 0.1803 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 C1 C 0.7635(4) 0.1924(4) 0.16275(19) 0.0231(8) Uani 1 1 d . . . C2 C 0.6979(5) 0.2166(5) 0.23647(19) 0.0283(8) Uani 1 1 d . . . H2A H 0.7799 0.2755 0.2646 0.034 Uiso 1 1 calc R . . H2B H 0.6756 0.1140 0.2589 0.034 Uiso 1 1 calc R . . C3 C 0.5357(5) 0.3113(6) 0.2282(2) 0.0336(9) Uani 1 1 d . . . H3A H 0.5330 0.4001 0.2613 0.040 Uiso 1 1 calc R . . H3B H 0.4375 0.2433 0.2367 0.040 Uiso 1 1 calc R . . C4 C 0.5340(5) 0.3733(5) 0.1536(2) 0.0314(9) Uani 1 1 d . . . H4A H 0.5043 0.4863 0.1526 0.038 Uiso 1 1 calc R . . H4B H 0.4519 0.3144 0.1255 0.038 Uiso 1 1 calc R . . C5 C 0.7123(5) 0.3481(5) 0.1254(2) 0.0286(8) Uani 1 1 d . . . C6 C 0.7155(6) 0.3309(6) 0.0473(2) 0.0449(12) Uani 1 1 d . . . H6A H 0.6823 0.4306 0.0259 0.067 Uiso 1 1 calc R . . H6B H 0.6376 0.2478 0.0333 0.067 Uiso 1 1 calc R . . H6C H 0.8285 0.3031 0.0323 0.067 Uiso 1 1 calc R . . C7 C 0.8238(5) 0.4835(5) 0.1493(3) 0.0375(10) Uani 1 1 d . . . H7A H 0.8005 0.5056 0.1985 0.045 Uiso 1 1 calc R . . H7B H 0.7955 0.5792 0.1226 0.045 Uiso 1 1 calc R . . C8 C 1.0101(6) 0.4491(5) 0.1408(3) 0.0455(12) Uani 1 1 d . . . H8A H 1.0362 0.4341 0.0914 0.055 Uiso 1 1 calc R . . H8B H 1.0759 0.5396 0.1579 0.055 Uiso 1 1 calc R . . C9 C 1.0574(5) 0.3011(5) 0.1810(2) 0.0370(10) Uani 1 1 d . . . H9A H 1.1764 0.2762 0.1728 0.044 Uiso 1 1 calc R . . H9B H 1.0425 0.3205 0.2309 0.044 Uiso 1 1 calc R . . C10 C 0.9517(5) 0.1634(5) 0.15953(19) 0.0260(8) Uani 1 1 d . . . C11 C 1.0089(4) 0.0265(5) 0.13563(19) 0.0242(8) Uani 1 1 d . . . H11 H 0.9280 -0.0517 0.1252 0.029 Uiso 1 1 calc R . . C12 C 1.1855(4) -0.0162(5) 0.12364(18) 0.0243(8) Uani 1 1 d . . . C13 C 1.3598(5) -0.2013(5) 0.0672(2) 0.0340(10) Uani 1 1 d . . . H13A H 1.4241 -0.2317 0.1087 0.041 Uiso 1 1 calc R . . H13B H 1.4204 -0.1158 0.0432 0.041 Uiso 1 1 calc R . . C14 C 1.3391(6) -0.3397(5) 0.0205(2) 0.0400(11) Uani 1 1 d . . . H14A H 1.2785 -0.4232 0.0447 0.060 Uiso 1 1 calc R . . H14B H 1.4492 -0.3787 0.0066 0.060 Uiso 1 1 calc R . . H14C H 1.2762 -0.3079 -0.0205 0.060 Uiso 1 1 calc R . . O1 O 0.6825(4) 0.0599(3) 0.13241(15) 0.0308(7) Uani 1 1 d . . . O2 O 1.3097(4) 0.0539(4) 0.14285(17) 0.0382(8) Uani 1 1 d . . . O3 O 1.1942(3) -0.1489(3) 0.08655(13) 0.0278(6) Uani 1 1 d . . . H1 H 0.583(7) 0.067(6) 0.136(2) 0.032(13) 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 C1 0.0198(17) 0.0199(18) 0.0295(18) -0.0026(14) 0.0012(14) -0.0033(13) C2 0.0216(17) 0.031(2) 0.0323(18) -0.0016(16) 0.0018(15) 0.0014(17) C3 0.0175(18) 0.046(2) 0.038(2) -0.0084(19) 0.0029(15) 0.0044(18) C4 0.0195(19) 0.032(2) 0.043(2) 0.0001(18) 0.0012(16) 0.0061(16) C5 0.0204(18) 0.029(2) 0.036(2) 0.0028(16) 0.0026(16) -0.0010(17) C6 0.034(2) 0.062(3) 0.038(2) 0.011(2) 0.0024(18) 0.007(2) C7 0.031(2) 0.0173(18) 0.064(3) 0.0033(18) 0.003(2) -0.0011(17) C8 0.028(2) 0.030(2) 0.079(4) -0.005(2) 0.008(2) -0.0100(19) C9 0.0180(18) 0.033(2) 0.060(3) -0.013(2) -0.0001(18) -0.0045(17) C10 0.0208(18) 0.028(2) 0.0287(17) 0.0000(15) -0.0009(14) 0.0003(15) C11 0.0168(17) 0.0255(19) 0.0304(18) -0.0017(15) -0.0011(15) 0.0003(15) C12 0.0177(16) 0.0243(18) 0.0308(17) 0.0016(14) -0.0016(15) 0.0031(15) C13 0.0190(18) 0.040(2) 0.043(2) -0.0014(18) 0.0053(16) 0.0090(18) C14 0.031(2) 0.039(2) 0.050(2) -0.010(2) 0.0057(19) 0.009(2) O1 0.0156(14) 0.0297(15) 0.0470(17) -0.0089(12) 0.0007(12) -0.0024(11) O2 0.0142(13) 0.0410(18) 0.0595(19) -0.0121(14) -0.0039(13) 0.0015(13) O3 0.0166(12) 0.0279(14) 0.0389(14) -0.0052(11) 0.0017(11) 0.0048(11) _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 1.426(4) . ? C1 C10 1.530(5) . ? C1 C2 1.538(5) . ? C1 C5 1.563(5) . ? C2 C3 1.538(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.541(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.544(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.524(6) . ? C5 C7 1.529(6) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.530(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.528(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.503(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.334(5) . ? C11 C12 1.480(5) . ? C11 H11 0.9500 . ? C12 O2 1.219(5) . ? C12 O3 1.339(5) . ? C13 O3 1.449(4) . ? C13 C14 1.494(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O1 H1 0.80(6) . ? 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 C10 107.7(3) . . ? O1 C1 C2 109.5(3) . . ? C10 C1 C2 113.4(3) . . ? O1 C1 C5 110.9(3) . . ? C10 C1 C5 112.1(3) . . ? C2 C1 C5 103.2(3) . . ? C1 C2 C3 105.2(3) . . ? C1 C2 H2A 110.7 . . ? C3 C2 H2A 110.7 . . ? C1 C2 H2B 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C2 C3 C4 106.5(3) . . ? C2 C3 H3A 110.4 . . ? C4 C3 H3A 110.4 . . ? C2 C3 H3B 110.4 . . ? C4 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? C3 C4 C5 106.1(3) . . ? C3 C4 H4A 110.5 . . ? C5 C4 H4A 110.5 . . ? C3 C4 H4B 110.5 . . ? C5 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? C6 C5 C7 111.4(4) . . ? C6 C5 C4 112.4(3) . . ? C7 C5 C4 109.2(3) . . ? C6 C5 C1 112.1(4) . . ? C7 C5 C1 110.0(3) . . ? C4 C5 C1 101.3(3) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 C8 113.2(4) . . ? C5 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C5 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C7 110.2(4) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 111.1(3) . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 125.6(4) . . ? C11 C10 C1 119.6(3) . . ? C9 C10 C1 114.8(3) . . ? C10 C11 C12 126.7(4) . . ? C10 C11 H11 116.7 . . ? C12 C11 H11 116.7 . . ? O2 C12 O3 122.2(3) . . ? O2 C12 C11 127.8(3) . . ? O3 C12 C11 109.9(3) . . ? O3 C13 C14 107.3(3) . . ? O3 C13 H13A 110.2 . . ? C14 C13 H13A 110.2 . . ? O3 C13 H13B 110.2 . . ? C14 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 O1 H1 111(3) . . ? C12 O3 C13 116.5(3) . . ? 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 O1 C1 C2 C3 -83.6(4) . . . . ? C10 C1 C2 C3 156.1(3) . . . . ? C5 C1 C2 C3 34.6(4) . . . . ? C1 C2 C3 C4 -13.4(4) . . . . ? C2 C3 C4 C5 -13.3(5) . . . . ? C3 C4 C5 C6 153.7(4) . . . . ? C3 C4 C5 C7 -82.1(4) . . . . ? C3 C4 C5 C1 34.0(4) . . . . ? O1 C1 C5 C6 -44.9(4) . . . . ? C10 C1 C5 C6 75.6(4) . . . . ? C2 C1 C5 C6 -162.1(3) . . . . ? O1 C1 C5 C7 -169.4(3) . . . . ? C10 C1 C5 C7 -48.9(4) . . . . ? C2 C1 C5 C7 73.4(4) . . . . ? O1 C1 C5 C4 75.1(4) . . . . ? C10 C1 C5 C4 -164.4(3) . . . . ? C2 C1 C5 C4 -42.1(4) . . . . ? C6 C5 C7 C8 -70.5(5) . . . . ? C4 C5 C7 C8 164.7(4) . . . . ? C1 C5 C7 C8 54.4(5) . . . . ? C5 C7 C8 C9 -58.2(5) . . . . ? C7 C8 C9 C10 55.6(5) . . . . ? C8 C9 C10 C11 123.3(4) . . . . ? C8 C9 C10 C1 -53.2(5) . . . . ? O1 C1 C10 C11 -4.4(5) . . . . ? C2 C1 C10 C11 116.9(4) . . . . ? C5 C1 C10 C11 -126.7(4) . . . . ? O1 C1 C10 C9 172.4(3) . . . . ? C2 C1 C10 C9 -66.3(5) . . . . ? C5 C1 C10 C9 50.1(4) . . . . ? C9 C10 C11 C12 -1.8(6) . . . . ? C1 C10 C11 C12 174.6(4) . . . . ? C10 C11 C12 O2 12.4(6) . . . . ? C10 C11 C12 O3 -167.3(4) . . . . ? O2 C12 O3 C13 -3.1(5) . . . . ? C11 C12 O3 C13 176.6(3) . . . . ? C14 C13 O3 C12 -174.1(3) . . . . ? 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 0.80(6) 2.20(6) 2.996(4) 172(5) 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.384 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.100 data_miesch12 _database_code_depnum_ccdc_archive 'CCDC 784205' #TrackingRef '02 cs lm mm TiCl4 6 6 lactone.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 O2' _chemical_formula_sum 'C13 H18 O2' _chemical_formula_weight 206.27 _chemical_absolute_configuration rm 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 0.0000 '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 0.0000 '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_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.3229(4) _cell_length_b 11.3609(5) _cell_length_c 11.8761(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1122.95(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3894 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 KappaCCD _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 6756 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1488 _reflns_number_gt 1341 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0481P)^2^+0.1557P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 1488 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 C1 C 0.15101(18) 0.45321(14) 0.38379(12) 0.0239(3) Uani 1 1 d . . . C2 C 0.1341(2) 0.40597(17) 0.50438(14) 0.0358(4) Uani 1 1 d . . . H2A H 0.2204 0.3480 0.5189 0.043 Uiso 1 1 calc R . . H2B H 0.1475 0.4717 0.5583 0.043 Uiso 1 1 calc R . . C3 C -0.0290(3) 0.3475(2) 0.5242(2) 0.0569(6) Uani 1 1 d . . . H3A H -0.0388 0.2770 0.4757 0.068 Uiso 1 1 calc R . . H3B H -0.0369 0.3217 0.6037 0.068 Uiso 1 1 calc R . . C4 C -0.1649(3) 0.4326(2) 0.4980(2) 0.0598(7) Uani 1 1 d . . . H4A H -0.2693 0.3922 0.5078 0.072 Uiso 1 1 calc R . . H4B H -0.1610 0.4996 0.5513 0.072 Uiso 1 1 calc R . . C5 C -0.1516(2) 0.4783(2) 0.37831(19) 0.0479(6) Uani 1 1 d . . . H5A H -0.2371 0.5375 0.3661 0.058 Uiso 1 1 calc R . . H5B H -0.1717 0.4122 0.3259 0.058 Uiso 1 1 calc R . . C6 C 0.0108(2) 0.53438(17) 0.34829(14) 0.0301(4) Uani 1 1 d . . . C7 C 0.0137(3) 0.5568(2) 0.22074(15) 0.0458(5) Uani 1 1 d . . . H7A H -0.0055 0.4826 0.1807 0.069 Uiso 1 1 calc R . . H7B H 0.1188 0.5883 0.1991 0.069 Uiso 1 1 calc R . . H7C H -0.0703 0.6136 0.2010 0.069 Uiso 1 1 calc R . . C8 C 0.0320(2) 0.65277(17) 0.41108(16) 0.0340(4) Uani 1 1 d . . . H8A H -0.0533 0.7076 0.3860 0.041 Uiso 1 1 calc R . . H8B H 0.0169 0.6390 0.4927 0.041 Uiso 1 1 calc R . . C9 C 0.1949(3) 0.71132(17) 0.39287(18) 0.0433(5) Uani 1 1 d . . . H9A H 0.2012 0.7834 0.4396 0.052 Uiso 1 1 calc R . . H9B H 0.2047 0.7351 0.3130 0.052 Uiso 1 1 calc R . . C10 C 0.3353(2) 0.62961(18) 0.42326(18) 0.0403(5) Uani 1 1 d . . . H10A H 0.4379 0.6644 0.3973 0.048 Uiso 1 1 calc R . . H10B H 0.3410 0.6193 0.5059 0.048 Uiso 1 1 calc R . . C11 C 0.30923(19) 0.51357(16) 0.36771(14) 0.0283(4) Uani 1 1 d . . . C12 C 0.3986(2) 0.45213(17) 0.29544(15) 0.0339(4) Uani 1 1 d . . . H12 H 0.5045 0.4718 0.2722 0.041 Uiso 1 1 calc R . . C13 C 0.30746(19) 0.34998(16) 0.25791(13) 0.0302(4) Uani 1 1 d . . . O1 O 0.16116(13) 0.35101(10) 0.30980(10) 0.0292(3) Uani 1 1 d . . . O2 O 0.34264(17) 0.27310(13) 0.19181(11) 0.0441(4) Uani 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 C1 0.0220(7) 0.0258(8) 0.0238(7) -0.0053(6) 0.0016(6) -0.0025(6) C2 0.0478(11) 0.0323(9) 0.0272(8) 0.0024(7) 0.0058(8) 0.0012(8) C3 0.0704(15) 0.0443(12) 0.0560(13) -0.0017(11) 0.0336(12) -0.0175(12) C4 0.0431(11) 0.0587(14) 0.0775(16) -0.0223(13) 0.0334(12) -0.0201(11) C5 0.0216(8) 0.0580(13) 0.0642(13) -0.0283(11) 0.0030(9) -0.0037(9) C6 0.0227(7) 0.0375(10) 0.0301(8) -0.0080(7) -0.0029(7) 0.0040(7) C7 0.0484(11) 0.0582(13) 0.0307(10) -0.0061(9) -0.0128(9) 0.0226(11) C8 0.0362(9) 0.0311(9) 0.0349(9) -0.0064(8) -0.0047(7) 0.0078(8) C9 0.0543(12) 0.0280(9) 0.0476(11) -0.0008(9) 0.0011(10) -0.0065(9) C10 0.0330(9) 0.0416(11) 0.0464(10) -0.0051(9) 0.0009(8) -0.0142(9) C11 0.0232(8) 0.0348(9) 0.0268(8) 0.0018(7) -0.0028(6) -0.0035(7) C12 0.0211(7) 0.0480(10) 0.0327(9) 0.0004(8) 0.0016(7) -0.0001(8) C13 0.0247(7) 0.0420(10) 0.0239(8) -0.0011(7) -0.0007(6) 0.0073(7) O1 0.0258(6) 0.0307(6) 0.0312(6) -0.0091(5) 0.0038(5) -0.0001(5) O2 0.0389(7) 0.0549(8) 0.0384(7) -0.0145(7) 0.0028(6) 0.0137(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 O1 1.4585(18) . ? C1 C11 1.497(2) . ? C1 C2 1.536(2) . ? C1 C6 1.546(2) . ? C2 C3 1.530(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.520(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.517(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.536(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.536(3) . ? C6 C8 1.548(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.525(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.536(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.490(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.333(2) . ? C12 C13 1.456(3) . ? C12 H12 0.9500 . ? C13 O2 1.210(2) . ? C13 O1 1.3647(19) . ? 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 C11 103.70(12) . . ? O1 C1 C2 106.79(13) . . ? C11 C1 C2 111.09(14) . . ? O1 C1 C6 110.75(12) . . ? C11 C1 C6 110.85(14) . . ? C2 C1 C6 113.17(13) . . ? C3 C2 C1 112.15(17) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 110.62(17) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 110.83(18) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 115.05(17) . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C5 C6 C7 108.14(17) . . ? C5 C6 C1 110.71(16) . . ? C7 C6 C1 110.85(14) . . ? C5 C6 C8 110.40(15) . . ? C7 C6 C8 109.23(17) . . ? C1 C6 C8 107.51(13) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C6 114.32(15) . . ? C9 C8 H8A 108.7 . . ? C6 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? C6 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 112.30(15) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 108.66(15) . . ? C11 C10 H10A 110.0 . . ? C9 C10 H10A 110.0 . . ? C11 C10 H10B 110.0 . . ? C9 C10 H10B 110.0 . . ? H10A C10 H10B 108.3 . . ? C12 C11 C10 131.84(16) . . ? C12 C11 C1 109.46(15) . . ? C10 C11 C1 118.49(15) . . ? C11 C12 C13 108.89(15) . . ? C11 C12 H12 125.6 . . ? C13 C12 H12 125.6 . . ? O2 C13 O1 121.00(17) . . ? O2 C13 C12 130.36(16) . . ? O1 C13 C12 108.64(14) . . ? C13 O1 C1 109.30(13) . . ? 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 O1 C1 C2 C3 -69.51(18) . . . . ? C11 C1 C2 C3 178.06(15) . . . . ? C6 C1 C2 C3 52.6(2) . . . . ? C1 C2 C3 C4 -56.5(2) . . . . ? C2 C3 C4 C5 56.5(2) . . . . ? C3 C4 C5 C6 -54.3(3) . . . . ? C4 C5 C6 C7 170.76(19) . . . . ? C4 C5 C6 C1 49.1(2) . . . . ? C4 C5 C6 C8 -69.8(2) . . . . ? O1 C1 C6 C5 72.41(17) . . . . ? C11 C1 C6 C5 -173.05(14) . . . . ? C2 C1 C6 C5 -47.47(19) . . . . ? O1 C1 C6 C7 -47.6(2) . . . . ? C11 C1 C6 C7 66.94(19) . . . . ? C2 C1 C6 C7 -167.48(17) . . . . ? O1 C1 C6 C8 -166.93(13) . . . . ? C11 C1 C6 C8 -52.39(17) . . . . ? C2 C1 C6 C8 73.20(18) . . . . ? C5 C6 C8 C9 176.07(17) . . . . ? C7 C6 C8 C9 -65.2(2) . . . . ? C1 C6 C8 C9 55.20(19) . . . . ? C6 C8 C9 C10 -55.2(2) . . . . ? C8 C9 C10 C11 49.1(2) . . . . ? C9 C10 C11 C12 122.2(2) . . . . ? C9 C10 C11 C1 -51.8(2) . . . . ? O1 C1 C11 C12 -1.02(17) . . . . ? C2 C1 C11 C12 113.36(16) . . . . ? C6 C1 C11 C12 -119.90(15) . . . . ? O1 C1 C11 C10 174.25(15) . . . . ? C2 C1 C11 C10 -71.4(2) . . . . ? C6 C1 C11 C10 55.37(19) . . . . ? C10 C11 C12 C13 -173.59(19) . . . . ? C1 C11 C12 C13 0.83(19) . . . . ? C11 C12 C13 O2 178.83(18) . . . . ? C11 C12 C13 O1 -0.30(19) . . . . ? O2 C13 O1 C1 -179.60(15) . . . . ? C12 C13 O1 C1 -0.37(17) . . . . ? C11 C1 O1 C13 0.82(16) . . . . ? C2 C1 O1 C13 -116.59(15) . . . . ? C6 C1 O1 C13 119.78(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.169 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.037 data_miesch11 _database_code_depnum_ccdc_archive 'CCDC 784206' #TrackingRef '03 cs lm mm TiCl4 6 6 cis.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H24 O3' _chemical_formula_sum 'C15 H24 O3' _chemical_formula_weight 252.34 _chemical_absolute_configuration rm 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 0.0000 '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 0.0000 '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_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.2735(3) _cell_length_b 9.0784(2) _cell_length_c 21.1524(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1396.73(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5216 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 KappaCCD _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 7385 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1854 _reflns_number_gt 1648 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0825P)^2^+0.1680P] 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 -10(10) _refine_ls_number_reflns 1854 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 C1 C 0.0950(3) 0.5556(2) 0.61773(9) 0.0254(4) Uani 1 1 d . . . C2 C 0.3008(3) 0.5623(2) 0.63638(10) 0.0293(4) Uani 1 1 d . . . H2A H 0.3134 0.6165 0.6767 0.035 Uiso 1 1 calc R . . H2B H 0.3472 0.4610 0.6430 0.035 Uiso 1 1 calc R . . C3 C 0.4168(3) 0.6379(2) 0.58583(10) 0.0331(5) Uani 1 1 d . . . H3A H 0.3771 0.7417 0.5814 0.040 Uiso 1 1 calc R . . H3B H 0.5475 0.6375 0.5989 0.040 Uiso 1 1 calc R . . C4 C 0.3974(3) 0.5597(3) 0.52245(10) 0.0340(5) Uani 1 1 d . . . H4A H 0.4676 0.6140 0.4898 0.041 Uiso 1 1 calc R . . H4B H 0.4492 0.4591 0.5257 0.041 Uiso 1 1 calc R . . C5 C 0.1961(3) 0.5505(2) 0.50299(10) 0.0312(5) Uani 1 1 d . . . H5A H 0.1874 0.4933 0.4632 0.037 Uiso 1 1 calc R . . H5B H 0.1510 0.6513 0.4941 0.037 Uiso 1 1 calc R . . C6 C 0.0690(3) 0.4793(2) 0.55250(9) 0.0269(4) Uani 1 1 d . . . C7 C -0.1304(3) 0.4980(3) 0.53004(10) 0.0338(5) Uani 1 1 d . . . H7A H -0.1577 0.6030 0.5250 0.051 Uiso 1 1 calc R . . H7B H -0.2140 0.4553 0.5614 0.051 Uiso 1 1 calc R . . H7C H -0.1466 0.4476 0.4894 0.051 Uiso 1 1 calc R . . C8 C 0.1125(3) 0.3133(2) 0.55832(11) 0.0355(5) Uani 1 1 d . . . H8A H 0.0859 0.2650 0.5174 0.043 Uiso 1 1 calc R . . H8B H 0.2454 0.3012 0.5670 0.043 Uiso 1 1 calc R . . C9 C 0.0038(4) 0.2357(2) 0.61008(12) 0.0441(6) Uani 1 1 d . . . H9A H 0.0452 0.1321 0.6133 0.053 Uiso 1 1 calc R . . H9B H -0.1282 0.2353 0.5987 0.053 Uiso 1 1 calc R . . C10 C 0.0285(4) 0.3118(2) 0.67447(11) 0.0389(5) Uani 1 1 d . . . H10A H -0.0554 0.2665 0.7058 0.047 Uiso 1 1 calc R . . H10B H 0.1562 0.2977 0.6894 0.047 Uiso 1 1 calc R . . C11 C -0.0123(3) 0.4746(2) 0.66927(9) 0.0287(4) Uani 1 1 d . . . C12 C -0.1341(3) 0.5479(2) 0.70467(9) 0.0294(4) Uani 1 1 d . . . H12 H -0.1573 0.6474 0.6933 0.035 Uiso 1 1 calc R . . C13 C -0.2363(3) 0.4897(3) 0.75980(10) 0.0343(5) Uani 1 1 d . . . C14 C -0.4880(4) 0.5432(3) 0.82914(11) 0.0478(6) Uani 1 1 d . . . H14A H -0.5390 0.6349 0.8474 0.057 Uiso 1 1 calc R . . H14B H -0.4085 0.4966 0.8614 0.057 Uiso 1 1 calc R . . C15 C -0.6418(4) 0.4412(3) 0.81295(12) 0.0518(7) Uani 1 1 d . . . H15A H -0.7203 0.4869 0.7808 0.078 Uiso 1 1 calc R . . H15B H -0.7146 0.4210 0.8509 0.078 Uiso 1 1 calc R . . H15C H -0.5914 0.3487 0.7965 0.078 Uiso 1 1 calc R . . O1 O 0.0289(2) 0.70328(15) 0.61047(7) 0.0280(3) Uani 1 1 d . . . O2 O -0.1988(3) 0.3821(2) 0.79107(9) 0.0544(5) Uani 1 1 d . . . O3 O -0.3784(3) 0.5792(2) 0.77388(7) 0.0421(4) Uani 1 1 d . . . H1O H 0.083(5) 0.762(4) 0.6385(15) 0.064(10) 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 C1 0.0297(9) 0.0227(8) 0.0237(9) -0.0009(7) -0.0020(8) 0.0033(8) C2 0.0301(10) 0.0289(9) 0.0290(9) -0.0046(8) -0.0060(8) 0.0019(9) C3 0.0274(10) 0.0372(10) 0.0348(11) -0.0083(9) 0.0001(9) -0.0014(9) C4 0.0292(10) 0.0403(11) 0.0324(10) -0.0068(9) 0.0021(9) 0.0016(10) C5 0.0310(10) 0.0375(10) 0.0252(9) -0.0031(9) -0.0006(8) 0.0041(10) C6 0.0280(10) 0.0283(9) 0.0245(9) -0.0048(8) -0.0027(8) 0.0000(8) C7 0.0297(10) 0.0416(11) 0.0300(10) -0.0040(9) -0.0051(8) -0.0008(10) C8 0.0396(11) 0.0264(9) 0.0406(11) -0.0091(9) -0.0022(10) 0.0007(10) C9 0.0563(15) 0.0238(9) 0.0523(15) -0.0021(9) 0.0001(13) -0.0042(11) C10 0.0504(13) 0.0250(9) 0.0414(12) 0.0072(9) -0.0009(11) 0.0009(10) C11 0.0338(10) 0.0255(9) 0.0267(9) 0.0032(8) -0.0043(8) -0.0029(9) C12 0.0334(10) 0.0300(9) 0.0247(9) 0.0059(8) -0.0006(8) -0.0023(9) C13 0.0412(11) 0.0367(10) 0.0250(9) 0.0054(9) -0.0017(9) -0.0089(10) C14 0.0501(15) 0.0592(15) 0.0342(12) -0.0003(11) 0.0133(11) -0.0129(14) C15 0.0531(15) 0.0695(17) 0.0328(12) 0.0028(12) 0.0075(11) -0.0191(15) O1 0.0356(8) 0.0224(6) 0.0260(7) 0.0008(6) 0.0012(6) 0.0030(6) O2 0.0648(13) 0.0570(11) 0.0413(10) 0.0252(9) 0.0042(10) 0.0004(10) O3 0.0415(9) 0.0498(9) 0.0348(8) 0.0065(7) 0.0121(7) -0.0047(8) _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 1.433(2) . ? C1 C11 1.529(3) . ? C1 C2 1.549(3) . ? C1 C6 1.555(3) . ? C2 C3 1.525(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.524(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.523(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.539(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.536(3) . ? C6 C8 1.545(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.523(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.538(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.511(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.337(3) . ? C12 C13 1.481(3) . ? C12 H12 0.9500 . ? C13 O2 1.211(3) . ? C13 O3 1.348(3) . ? C14 O3 1.452(3) . ? C14 C15 1.492(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? O1 H1O 0.89(4) . ? 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 C11 110.80(16) . . ? O1 C1 C2 108.33(17) . . ? C11 C1 C2 109.32(16) . . ? O1 C1 C6 106.31(15) . . ? C11 C1 C6 110.89(16) . . ? C2 C1 C6 111.15(16) . . ? C3 C2 C1 111.96(17) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 110.83(18) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 110.64(18) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 114.59(17) . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C5 108.05(17) . . ? C7 C6 C8 109.03(19) . . ? C5 C6 C8 109.96(17) . . ? C7 C6 C1 109.87(17) . . ? C5 C6 C1 110.10(17) . . ? C8 C6 C1 109.80(16) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C6 113.70(18) . . ? C9 C8 H8A 108.8 . . ? C6 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C6 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 111.62(19) . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 110.60(18) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 125.2(2) . . ? C12 C11 C1 119.89(17) . . ? C10 C11 C1 114.95(19) . . ? C11 C12 C13 126.61(19) . . ? C11 C12 H12 116.7 . . ? C13 C12 H12 116.7 . . ? O2 C13 O3 122.6(2) . . ? O2 C13 C12 127.2(2) . . ? O3 C13 C12 110.13(18) . . ? O3 C14 C15 111.5(2) . . ? O3 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? O3 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C1 O1 H1O 110(2) . . ? C13 O3 C14 117.58(19) . . ? 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 O1 C1 C2 C3 -60.9(2) . . . . ? C11 C1 C2 C3 178.29(16) . . . . ? C6 C1 C2 C3 55.6(2) . . . . ? C1 C2 C3 C4 -57.6(2) . . . . ? C2 C3 C4 C5 55.7(2) . . . . ? C3 C4 C5 C6 -54.5(3) . . . . ? C4 C5 C6 C7 172.16(19) . . . . ? C4 C5 C6 C8 -68.9(2) . . . . ? C4 C5 C6 C1 52.2(2) . . . . ? O1 C1 C6 C7 -52.5(2) . . . . ? C11 C1 C6 C7 68.0(2) . . . . ? C2 C1 C6 C7 -170.20(18) . . . . ? O1 C1 C6 C5 66.4(2) . . . . ? C11 C1 C6 C5 -173.13(16) . . . . ? C2 C1 C6 C5 -51.3(2) . . . . ? O1 C1 C6 C8 -172.43(17) . . . . ? C11 C1 C6 C8 -51.9(2) . . . . ? C2 C1 C6 C8 69.9(2) . . . . ? C7 C6 C8 C9 -66.3(2) . . . . ? C5 C6 C8 C9 175.40(18) . . . . ? C1 C6 C8 C9 54.1(2) . . . . ? C6 C8 C9 C10 -54.7(3) . . . . ? C8 C9 C10 C11 52.3(3) . . . . ? C9 C10 C11 C12 125.1(2) . . . . ? C9 C10 C11 C1 -53.5(3) . . . . ? O1 C1 C11 C12 -6.8(3) . . . . ? C2 C1 C11 C12 112.5(2) . . . . ? C6 C1 C11 C12 -124.6(2) . . . . ? O1 C1 C11 C10 171.86(18) . . . . ? C2 C1 C11 C10 -68.8(2) . . . . ? C6 C1 C11 C10 54.1(2) . . . . ? C10 C11 C12 C13 7.3(4) . . . . ? C1 C11 C12 C13 -174.16(19) . . . . ? C11 C12 C13 O2 18.7(4) . . . . ? C11 C12 C13 O3 -164.5(2) . . . . ? O2 C13 O3 C14 0.3(3) . . . . ? C12 C13 O3 C14 -176.61(19) . . . . ? C15 C14 O3 C13 -88.6(3) . . . . ? 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 H1O O2 0.89(4) 2.03(4) 2.916(2) 175(3) 4_556 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.364 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.054