# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a14020 _database_code_depnum_ccdc_archive 'CCDC 912316' #TrackingRef '15628_web_deposit_cif_file_0_Chia-JungLiang_1353676544.a14020.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 O4' _chemical_formula_sum 'C9 H14 O4' _chemical_formula_weight 186.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.7917(6) _cell_length_b 16.0545(16) _cell_length_c 18.954(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.0100(10) _cell_angle_gamma 90.00 _cell_volume 1762.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9773 _exptl_absorpt_correction_T_max 0.9989 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12654 _diffrn_reflns_av_R_equivalents 0.1180 _diffrn_reflns_av_sigmaI/netI 0.1767 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.07 _reflns_number_total 3075 _reflns_number_gt 1389 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0809P)^2^+13.9296P] 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 SHELXL _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3075 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2419 _refine_ls_R_factor_gt 0.1280 _refine_ls_wR_factor_ref 0.3449 _refine_ls_wR_factor_gt 0.2915 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 C1 C 0.9860(18) 0.5595(6) 0.3556(5) 0.043(3) Uani 1 1 d . . . C2 C 0.725(2) 0.5660(7) 0.3534(9) 0.102(6) Uani 1 1 d . . . H2A H 0.6691 0.6016 0.3925 0.122 Uiso 1 1 calc R . . H2B H 0.6750 0.5912 0.3082 0.122 Uiso 1 1 calc R . . C3 C 0.6337(16) 0.4856(6) 0.3599(6) 0.052(3) Uani 1 1 d . . . H3A H 0.5603 0.4681 0.3151 0.062 Uiso 1 1 calc R . . H3B H 0.5162 0.4839 0.3978 0.062 Uiso 1 1 calc R . . C4 C 0.8331(14) 0.4287(5) 0.3776(5) 0.036(2) Uani 1 1 d . . . C5 C 0.8573(13) 0.3568(5) 0.3266(6) 0.040(3) Uani 1 1 d . . . H5 H 0.8686 0.3802 0.2779 0.048 Uiso 1 1 calc R . . C6 C 1.0718(14) 0.3049(5) 0.3402(5) 0.036(2) Uani 1 1 d . . . H6 H 1.2117 0.3407 0.3340 0.044 Uiso 1 1 calc R . . C7 C 1.0636(16) 0.2721(6) 0.4184(5) 0.045(3) Uani 1 1 d . . . H7A H 0.9284 0.2350 0.4245 0.054 Uiso 1 1 calc R . . H7B H 1.2046 0.2393 0.4285 0.054 Uiso 1 1 calc R . . C8 C 1.0474(16) 0.3432(6) 0.4688(6) 0.050(3) Uani 1 1 d . . . H8A H 1.1881 0.3780 0.4650 0.060 Uiso 1 1 calc R . . H8B H 1.0384 0.3216 0.5176 0.060 Uiso 1 1 calc R . . C9 C 0.8374(15) 0.3961(6) 0.4536(5) 0.046(3) Uani 1 1 d . . . H9A H 0.8351 0.4439 0.4865 0.055 Uiso 1 1 calc R . . H9B H 0.6967 0.3626 0.4622 0.055 Uiso 1 1 calc R . . C10 C 0.4890(18) 0.5552(6) 0.1562(6) 0.050(3) Uani 1 1 d . . . C11 C 0.2437(19) 0.5588(7) 0.1717(7) 0.069(4) Uani 1 1 d . . . H11A H 0.1792 0.6134 0.1575 0.083 Uiso 1 1 calc R . . H11B H 0.2166 0.5508 0.2228 0.083 Uiso 1 1 calc R . . C12 C 0.1351(15) 0.4913(5) 0.1311(6) 0.044(3) Uani 1 1 d . . . H12A H 0.0624 0.5132 0.0876 0.053 Uiso 1 1 calc R . . H12B H 0.0161 0.4625 0.1596 0.053 Uiso 1 1 calc R . . C13 C 0.3324(13) 0.4325(5) 0.1133(5) 0.033(2) Uani 1 1 d . . . C14 C 0.3571(13) 0.3598(5) 0.1658(5) 0.031(2) Uani 1 1 d . . . H14 H 0.3692 0.3816 0.2151 0.037 Uiso 1 1 calc R . . C15 C 0.5715(14) 0.3092(5) 0.1472(5) 0.030(2) Uani 1 1 d . . . H15 H 0.7115 0.3451 0.1527 0.036 Uiso 1 1 calc R . . C16 C 0.5636(17) 0.2756(6) 0.0733(5) 0.046(3) Uani 1 1 d . . . H16A H 0.4282 0.2385 0.0678 0.055 Uiso 1 1 calc R . . H16B H 0.7046 0.2426 0.0637 0.055 Uiso 1 1 calc R . . C17 C 0.5469(16) 0.3483(6) 0.0210(5) 0.048(3) Uani 1 1 d . . . H17A H 0.5354 0.3265 -0.0278 0.058 Uiso 1 1 calc R . . H17B H 0.6875 0.3831 0.0242 0.058 Uiso 1 1 calc R . . C18 C 0.3323(15) 0.4014(6) 0.0381(5) 0.040(2) Uani 1 1 d . . . H18A H 0.3269 0.4497 0.0056 0.048 Uiso 1 1 calc R . . H18B H 0.1918 0.3676 0.0300 0.048 Uiso 1 1 calc R . . O1 O 1.1332(13) 0.6103(4) 0.3477(4) 0.067(2) Uani 1 1 d . . . O2 O 1.0381(10) 0.4804(4) 0.3685(4) 0.054(2) Uani 1 1 d . . . O3 O 0.6545(9) 0.3073(4) 0.3303(3) 0.0423(18) Uani 1 1 d . . . H3 H 0.5385 0.3373 0.3225 0.063 Uiso 1 1 calc R . . O4 O 1.0793(10) 0.2388(4) 0.2907(3) 0.0415(18) Uani 1 1 d . . . H4' H 1.2561 0.2363 0.2729 0.050 Uiso 1 1 d R . . O5 O 0.6413(13) 0.6036(5) 0.1692(4) 0.071(3) Uani 1 1 d . . . O6 O 0.5413(9) 0.4845(3) 0.1232(3) 0.0356(16) Uani 1 1 d . . . O7 O 0.1521(9) 0.3121(4) 0.1578(3) 0.0410(18) Uani 1 1 d . . . H7' H 0.1399 0.2583 0.1901 0.049 Uiso 1 1 d R . . O8 O 0.5790(10) 0.2418(3) 0.1996(4) 0.0410(18) Uani 1 1 d . . . H8' H 0.6717 0.2005 0.1809 0.049 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.066(7) 0.035(6) 0.028(6) 0.010(5) -0.005(5) -0.009(5) C2 0.067(9) 0.054(8) 0.185(17) 0.035(9) -0.059(9) 0.006(7) C3 0.039(6) 0.043(6) 0.073(9) 0.007(6) 0.000(5) 0.001(5) C4 0.024(5) 0.025(5) 0.060(7) 0.008(5) -0.005(4) -0.005(4) C5 0.019(5) 0.040(6) 0.061(7) 0.020(5) -0.002(4) -0.004(4) C6 0.025(5) 0.028(5) 0.057(7) 0.008(5) -0.001(4) 0.003(4) C7 0.037(6) 0.042(6) 0.055(8) 0.021(5) -0.001(5) 0.002(4) C8 0.040(6) 0.049(6) 0.062(8) 0.006(6) -0.010(5) -0.006(5) C9 0.031(5) 0.053(6) 0.054(8) 0.002(5) 0.005(5) -0.008(4) C10 0.051(7) 0.034(6) 0.066(8) 0.000(6) 0.010(6) 0.005(5) C11 0.065(8) 0.053(7) 0.089(10) -0.020(7) 0.020(7) 0.001(6) C12 0.037(5) 0.033(5) 0.063(8) 0.003(5) -0.005(5) 0.010(4) C13 0.022(4) 0.029(5) 0.049(7) -0.007(5) -0.010(4) -0.001(4) C14 0.025(5) 0.027(5) 0.040(6) -0.003(4) 0.001(4) -0.001(4) C15 0.032(5) 0.022(4) 0.035(6) 0.000(4) -0.005(4) -0.001(4) C16 0.043(6) 0.043(6) 0.052(7) -0.014(5) 0.001(5) 0.006(5) C17 0.043(6) 0.059(7) 0.043(7) -0.017(6) 0.003(5) -0.002(5) C18 0.043(6) 0.035(5) 0.043(7) 0.002(5) -0.007(5) 0.000(4) O1 0.068(5) 0.036(4) 0.098(7) 0.011(4) -0.009(5) -0.021(4) O2 0.028(4) 0.032(4) 0.102(6) 0.017(4) 0.001(4) -0.002(3) O3 0.020(3) 0.045(4) 0.062(5) 0.004(3) 0.003(3) 0.001(3) O4 0.036(4) 0.038(4) 0.051(5) 0.004(3) 0.006(3) 0.003(3) O5 0.065(5) 0.056(5) 0.093(7) -0.035(5) 0.008(5) -0.022(4) O6 0.031(3) 0.026(3) 0.050(4) -0.001(3) -0.003(3) -0.006(3) O7 0.027(3) 0.034(3) 0.062(5) 0.009(3) 0.002(3) -0.007(3) O8 0.040(4) 0.027(3) 0.057(5) -0.005(3) -0.001(3) 0.008(3) _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 1.189(11) . ? C1 O2 1.328(11) . ? C1 C2 1.517(15) . ? C2 C3 1.400(14) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.511(12) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O2 1.460(10) . ? C4 C5 1.512(13) . ? C4 C9 1.532(13) . ? C5 O3 1.419(9) . ? C5 C6 1.517(11) . ? C5 H5 1.0000 . ? C6 O4 1.417(11) . ? C6 C7 1.573(13) . ? C6 H6 1.0000 . ? C7 C8 1.492(14) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.510(13) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O5 1.200(12) . ? C10 O6 1.332(11) . ? C10 C11 1.452(14) . ? C11 C12 1.470(14) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.520(11) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O6 1.482(9) . ? C13 C18 1.510(13) . ? C13 C14 1.540(12) . ? C14 O7 1.421(9) . ? C14 C15 1.525(11) . ? C14 H14 1.0000 . ? C15 O8 1.471(10) . ? C15 C16 1.501(13) . ? C15 H15 1.0000 . ? C16 C17 1.535(14) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.541(12) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O3 H3 0.8400 . ? O4 H4' 1.0788 . ? O7 H7' 1.0600 . ? O8 H8' 0.9242 . ? 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 O2 121.0(10) . . ? O1 C1 C2 131.7(10) . . ? O2 C1 C2 107.3(8) . . ? C3 C2 C1 108.1(9) . . ? C3 C2 H2A 110.1 . . ? C1 C2 H2A 110.1 . . ? C3 C2 H2B 110.1 . . ? C1 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? C2 C3 C4 106.8(8) . . ? 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 . . ? O2 C4 C3 104.5(7) . . ? O2 C4 C5 106.4(7) . . ? C3 C4 C5 113.0(8) . . ? O2 C4 C9 107.0(7) . . ? C3 C4 C9 115.4(8) . . ? C5 C4 C9 109.8(7) . . ? O3 C5 C4 108.6(7) . . ? O3 C5 C6 111.2(7) . . ? C4 C5 C6 112.7(8) . . ? O3 C5 H5 108.1 . . ? C4 C5 H5 108.1 . . ? C6 C5 H5 108.1 . . ? O4 C6 C5 108.9(8) . . ? O4 C6 C7 111.9(7) . . ? C5 C6 C7 108.6(7) . . ? O4 C6 H6 109.1 . . ? C5 C6 H6 109.1 . . ? C7 C6 H6 109.1 . . ? C8 C7 C6 110.4(8) . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 111.0(8) . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C4 112.6(8) . . ? C8 C9 H9A 109.1 . . ? C4 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C4 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? O5 C10 O6 118.7(9) . . ? O5 C10 C11 130.7(10) . . ? O6 C10 C11 110.6(9) . . ? C10 C11 C12 106.5(9) . . ? C10 C11 H11A 110.4 . . ? C12 C11 H11A 110.4 . . ? C10 C11 H11B 110.4 . . ? C12 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? C11 C12 C13 104.6(8) . . ? C11 C12 H12A 110.8 . . ? C13 C12 H12A 110.8 . . ? C11 C12 H12B 110.8 . . ? C13 C12 H12B 110.8 . . ? H12A C12 H12B 108.9 . . ? O6 C13 C18 107.8(7) . . ? O6 C13 C12 103.6(6) . . ? C18 C13 C12 114.5(8) . . ? O6 C13 C14 105.6(6) . . ? C18 C13 C14 111.0(7) . . ? C12 C13 C14 113.4(8) . . ? O7 C14 C15 111.7(7) . . ? O7 C14 C13 105.2(7) . . ? C15 C14 C13 109.2(7) . . ? O7 C14 H14 110.2 . . ? C15 C14 H14 110.2 . . ? C13 C14 H14 110.2 . . ? O8 C15 C16 111.5(7) . . ? O8 C15 C14 105.0(7) . . ? C16 C15 C14 112.5(7) . . ? O8 C15 H15 109.2 . . ? C16 C15 H15 109.2 . . ? C14 C15 H15 109.2 . . ? C15 C16 C17 109.3(8) . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16B 109.8 . . ? C17 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? C16 C17 C18 109.6(8) . . ? C16 C17 H17A 109.8 . . ? C18 C17 H17A 109.8 . . ? C16 C17 H17B 109.8 . . ? C18 C17 H17B 109.8 . . ? H17A C17 H17B 108.2 . . ? C13 C18 C17 112.4(8) . . ? C13 C18 H18A 109.1 . . ? C17 C18 H18A 109.1 . . ? C13 C18 H18B 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C1 O2 C4 112.4(7) . . ? C5 O3 H3 109.5 . . ? C6 O4 H4' 105.3 . . ? C10 O6 C13 110.8(7) . . ? C14 O7 H7' 115.7 . . ? C15 O8 H8' 106.6 . . ? 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 174.6(12) . . . . ? O2 C1 C2 C3 -4.7(15) . . . . ? C1 C2 C3 C4 8.6(16) . . . . ? C2 C3 C4 O2 -9.2(13) . . . . ? C2 C3 C4 C5 -124.5(11) . . . . ? C2 C3 C4 C9 108.0(12) . . . . ? O2 C4 C5 O3 -176.3(7) . . . . ? C3 C4 C5 O3 -62.2(10) . . . . ? C9 C4 C5 O3 68.2(9) . . . . ? O2 C4 C5 C6 60.0(9) . . . . ? C3 C4 C5 C6 174.1(8) . . . . ? C9 C4 C5 C6 -55.5(9) . . . . ? O3 C5 C6 O4 57.2(10) . . . . ? C4 C5 C6 O4 179.4(7) . . . . ? O3 C5 C6 C7 -64.9(10) . . . . ? C4 C5 C6 C7 57.3(9) . . . . ? O4 C6 C7 C8 -178.0(7) . . . . ? C5 C6 C7 C8 -57.8(10) . . . . ? C6 C7 C8 C9 57.7(10) . . . . ? C7 C8 C9 C4 -56.4(11) . . . . ? O2 C4 C9 C8 -61.2(10) . . . . ? C3 C4 C9 C8 -177.0(8) . . . . ? C5 C4 C9 C8 53.9(10) . . . . ? O5 C10 C11 C12 168.8(13) . . . . ? O6 C10 C11 C12 -12.5(13) . . . . ? C10 C11 C12 C13 19.2(12) . . . . ? C11 C12 C13 O6 -18.8(10) . . . . ? C11 C12 C13 C18 -136.0(9) . . . . ? C11 C12 C13 C14 95.2(10) . . . . ? O6 C13 C14 O7 177.8(6) . . . . ? C18 C13 C14 O7 -65.6(8) . . . . ? C12 C13 C14 O7 65.0(9) . . . . ? O6 C13 C14 C15 -62.2(8) . . . . ? C18 C13 C14 C15 54.4(9) . . . . ? C12 C13 C14 C15 -175.0(7) . . . . ? O7 C14 C15 O8 -63.8(9) . . . . ? C13 C14 C15 O8 -179.8(6) . . . . ? O7 C14 C15 C16 57.7(10) . . . . ? C13 C14 C15 C16 -58.3(9) . . . . ? O8 C15 C16 C17 177.9(7) . . . . ? C14 C15 C16 C17 60.2(10) . . . . ? C15 C16 C17 C18 -57.2(10) . . . . ? O6 C13 C18 C17 60.2(9) . . . . ? C12 C13 C18 C17 175.0(8) . . . . ? C14 C13 C18 C17 -55.0(9) . . . . ? C16 C17 C18 C13 56.1(10) . . . . ? O1 C1 O2 C4 179.1(10) . . . . ? C2 C1 O2 C4 -1.4(12) . . . . ? C3 C4 O2 C1 6.5(11) . . . . ? C5 C4 O2 C1 126.3(8) . . . . ? C9 C4 O2 C1 -116.3(9) . . . . ? O5 C10 O6 C13 178.8(10) . . . . ? C11 C10 O6 C13 -0.1(12) . . . . ? C18 C13 O6 C10 133.9(8) . . . . ? C12 C13 O6 C10 12.1(10) . . . . ? C14 C13 O6 C10 -107.4(8) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.384 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.088 data_ch14189 _database_code_depnum_ccdc_archive 'CCDC 912317' #TrackingRef 'web_deposit_cif_file_1_Chia-JungLiang_1353676544.ch14189.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 O4' _chemical_formula_sum 'C10 H16 O4' _chemical_formula_weight 200.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3977(3) _cell_length_b 9.1656(3) _cell_length_c 14.8408(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.475(2) _cell_angle_gamma 90.00 _cell_volume 992.54(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9447 _exptl_absorpt_correction_T_max 0.9669 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6588 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 25.04 _reflns_number_total 1741 _reflns_number_gt 1465 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0650P)^2^+0.2810P] 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 1741 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 -0.0655(2) 0.50468(17) 0.21818(11) 0.0373(4) Uani 1 1 d . . . C2 C -0.0398(3) 0.3977(2) 0.29472(13) 0.0577(5) Uani 1 1 d . . . H2A H -0.1574 0.3681 0.3094 0.069 Uiso 1 1 calc R . . H2B H 0.0325 0.4403 0.3488 0.069 Uiso 1 1 calc R . . C3 C 0.0575(3) 0.2700(2) 0.26294(11) 0.0490(5) Uani 1 1 d . . . H3A H -0.0231 0.1859 0.2533 0.059 Uiso 1 1 calc R . . H3B H 0.1641 0.2446 0.3074 0.059 Uiso 1 1 calc R . . C4 C 0.1148(2) 0.31904(16) 0.17244(10) 0.0360(4) Uani 1 1 d . . . C5 C 0.0472(2) 0.21751(15) 0.08991(10) 0.0337(4) Uani 1 1 d . . . C6 C -0.1600(2) 0.2010(2) 0.07158(13) 0.0485(5) Uani 1 1 d . . . H6A H -0.2008 0.1633 0.1251 0.073 Uiso 1 1 calc R . . H6B H -0.1945 0.1349 0.0215 0.073 Uiso 1 1 calc R . . H6C H -0.2155 0.2944 0.0565 0.073 Uiso 1 1 calc R . . C7 C 0.1165(2) 0.27750(16) 0.00542(10) 0.0348(4) Uani 1 1 d . . . H7 H 0.0587 0.3727 -0.0091 0.042 Uiso 1 1 calc R . . C8 C 0.3214(3) 0.2986(2) 0.01904(12) 0.0456(4) Uani 1 1 d . . . H8A H 0.3567 0.3358 -0.0367 0.055 Uiso 1 1 calc R . . H8B H 0.3822 0.2056 0.0331 0.055 Uiso 1 1 calc R . . C9 C 0.3803(3) 0.4053(2) 0.09677(13) 0.0492(5) Uani 1 1 d . . . H9A H 0.3268 0.5004 0.0808 0.059 Uiso 1 1 calc R . . H9B H 0.5126 0.4156 0.1071 0.059 Uiso 1 1 calc R . . C10 C 0.3179(3) 0.34997(19) 0.18335(12) 0.0446(4) Uani 1 1 d . . . H10A H 0.3844 0.2612 0.2028 0.054 Uiso 1 1 calc R . . H10B H 0.3495 0.4220 0.2312 0.054 Uiso 1 1 calc R . . O1 O -0.14520(17) 0.62006(13) 0.21239(9) 0.0509(4) Uani 1 1 d . . . O2 O 0.02029(17) 0.45972(11) 0.15113(7) 0.0426(3) Uani 1 1 d . . . O3 O 0.13397(17) 0.08061(11) 0.11597(8) 0.0433(3) Uani 1 1 d . . . H3' H 0.0623 0.0005 0.0951 0.052 Uiso 1 1 d R . . O4 O 0.05668(18) 0.18126(13) -0.07011(8) 0.0473(4) Uani 1 1 d . . . H4' H 0.0776 0.2347 -0.1221 0.057 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0381(9) 0.0354(9) 0.0403(8) -0.0075(7) 0.0118(7) -0.0051(7) C2 0.0834(15) 0.0466(11) 0.0505(11) 0.0029(8) 0.0325(10) -0.0038(10) C3 0.0699(13) 0.0410(10) 0.0376(9) 0.0084(7) 0.0130(8) 0.0004(9) C4 0.0475(10) 0.0259(8) 0.0354(8) 0.0045(6) 0.0094(7) 0.0069(7) C5 0.0376(9) 0.0262(7) 0.0377(8) 0.0040(6) 0.0073(7) 0.0026(6) C6 0.0399(11) 0.0513(10) 0.0553(11) 0.0037(8) 0.0108(8) -0.0033(8) C7 0.0439(10) 0.0263(8) 0.0348(8) -0.0029(6) 0.0086(7) -0.0017(7) C8 0.0454(11) 0.0437(9) 0.0513(10) -0.0066(8) 0.0183(8) -0.0051(8) C9 0.0417(10) 0.0469(10) 0.0599(11) -0.0077(8) 0.0115(8) -0.0107(8) C10 0.0501(11) 0.0368(9) 0.0437(9) -0.0054(7) -0.0019(8) -0.0010(8) O1 0.0539(8) 0.0423(7) 0.0598(8) -0.0072(6) 0.0192(6) 0.0097(6) O2 0.0622(8) 0.0320(6) 0.0368(6) 0.0053(5) 0.0177(5) 0.0136(5) O3 0.0516(7) 0.0243(6) 0.0520(7) 0.0046(5) 0.0023(6) 0.0023(5) O4 0.0662(9) 0.0388(6) 0.0373(6) -0.0063(5) 0.0097(6) -0.0128(6) _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 1.207(2) . ? C1 O2 1.3307(19) . ? C1 C2 1.489(2) . ? C2 C3 1.491(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.541(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O2 1.4759(18) . ? C4 C10 1.511(3) . ? C4 C5 1.554(2) . ? C5 O3 1.4332(18) . ? C5 C6 1.519(2) . ? C5 C7 1.532(2) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 O4 1.4377(18) . ? C7 C8 1.508(2) . ? C7 H7 0.9800 . ? C8 C9 1.521(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.522(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? O3 H3' 0.9284 . ? O4 H4' 0.9477 . ? 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 O2 120.37(15) . . ? O1 C1 C2 129.13(16) . . ? O2 C1 C2 110.46(14) . . ? C1 C2 C3 106.48(14) . . ? C1 C2 H2A 110.4 . . ? C3 C2 H2A 110.4 . . ? C1 C2 H2B 110.4 . . ? C3 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? C2 C3 C4 105.24(14) . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3B 110.7 . . ? C4 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? O2 C4 C10 106.65(13) . . ? O2 C4 C3 104.68(13) . . ? C10 C4 C3 111.89(14) . . ? O2 C4 C5 105.95(12) . . ? C10 C4 C5 112.44(13) . . ? C3 C4 C5 114.42(13) . . ? O3 C5 C6 110.78(13) . . ? O3 C5 C7 109.86(13) . . ? C6 C5 C7 110.64(13) . . ? O3 C5 C4 103.89(12) . . ? C6 C5 C4 112.62(14) . . ? C7 C5 C4 108.82(12) . . ? 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 . . ? O4 C7 C8 110.89(13) . . ? O4 C7 C5 108.44(12) . . ? C8 C7 C5 113.59(14) . . ? O4 C7 H7 107.9 . . ? C8 C7 H7 107.9 . . ? C5 C7 H7 107.9 . . ? C7 C8 C9 109.90(14) . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C8 C9 C10 109.69(15) . . ? C8 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? C8 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C4 C10 C9 113.99(14) . . ? C4 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? C4 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.6 . . ? C1 O2 C4 112.19(12) . . ? C5 O3 H3' 113.4 . . ? C7 O4 H4' 104.3 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.157 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.060 data_a14175 _database_code_depnum_ccdc_archive 'CCDC 912318' #TrackingRef 'web_deposit_cif_file_2_Chia-JungLiang_1353676544.a14175.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H18 O4' _chemical_formula_sum 'C11 H18 O4' _chemical_formula_weight 214.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.1080(3) _cell_length_b 9.3204(2) _cell_length_c 16.7632(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.4030(10) _cell_angle_gamma 90.00 _cell_volume 2182.32(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9702 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13226 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3820 _reflns_number_gt 3220 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0715P)^2^+1.2125P] 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 3820 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 0.814 _refine_ls_restrained_S_all 0.814 _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 0.26384(10) 1.06943(16) 0.41708(9) 0.0225(3) Uani 1 1 d . . . C2 C 0.17587(10) 0.97799(15) 0.39090(10) 0.0251(3) Uani 1 1 d . . . H2A H 0.1348 0.9946 0.3310 0.030 Uiso 1 1 calc R . . H2B H 0.1399 0.9971 0.4269 0.030 Uiso 1 1 calc R . . C3 C 0.21480(10) 0.82564(16) 0.40406(10) 0.0271(3) Uani 1 1 d . . . H3A H 0.2176 0.7873 0.3513 0.033 Uiso 1 1 calc R . . H3B H 0.1758 0.7629 0.4235 0.033 Uiso 1 1 calc R . . C4 C 0.31558(10) 0.84315(14) 0.47395(10) 0.0224(3) Uani 1 1 d . . . C5 C 0.39006(10) 0.74395(15) 0.46198(10) 0.0256(3) Uani 1 1 d . . . H5 H 0.3956 0.7660 0.4069 0.031 Uiso 1 1 calc R . . C6 C 0.48717(10) 0.76271(15) 0.53471(11) 0.0270(3) Uani 1 1 d . . . H6 H 0.5100 0.8602 0.5319 0.032 Uiso 1 1 calc R . . C7 C 0.48255(10) 0.74108(16) 0.62259(10) 0.0280(3) Uani 1 1 d . . . H7A H 0.5461 0.7532 0.6667 0.034 Uiso 1 1 calc R . . H7B H 0.4619 0.6437 0.6266 0.034 Uiso 1 1 calc R . . C8 C 0.41356(10) 0.84673(16) 0.63984(10) 0.0265(3) Uani 1 1 d . . . C9 C 0.40020(13) 0.80532(19) 0.72285(11) 0.0381(4) Uani 1 1 d . . . H9A H 0.3568 0.8714 0.7329 0.057 Uiso 1 1 calc R . . H9B H 0.4609 0.8086 0.7705 0.057 Uiso 1 1 calc R . . H9C H 0.3745 0.7100 0.7173 0.057 Uiso 1 1 calc R . . C10 C 0.45416(11) 0.99966(16) 0.65150(11) 0.0326(4) Uani 1 1 d . . . H10A H 0.4632 1.0286 0.6002 0.049 Uiso 1 1 calc R . . H10B H 0.5145 1.0020 0.6996 0.049 Uiso 1 1 calc R . . H10C H 0.4102 1.0641 0.6620 0.049 Uiso 1 1 calc R . . C11 C 0.31557(10) 0.83535(15) 0.56471(9) 0.0236(3) Uani 1 1 d . . . H11A H 0.2864 0.7452 0.5703 0.028 Uiso 1 1 calc R . . H11B H 0.2751 0.9118 0.5709 0.028 Uiso 1 1 calc R . . C12 C 0.06703(10) 0.18831(16) 0.79134(9) 0.0250(3) Uani 1 1 d . . . C13 C 0.10784(12) 0.04039(17) 0.80666(10) 0.0316(4) Uani 1 1 d . . . H13A H 0.0573 -0.0308 0.7870 0.038 Uiso 1 1 calc R . . H13B H 0.1451 0.0250 0.8675 0.038 Uiso 1 1 calc R . . C14 C 0.17098(11) 0.03127(16) 0.75495(10) 0.0276(3) Uani 1 1 d . . . H14A H 0.1595 -0.0574 0.7223 0.033 Uiso 1 1 calc R . . H14B H 0.2381 0.0359 0.7926 0.033 Uiso 1 1 calc R . . C15 C 0.14259(10) 0.16170(15) 0.69412(9) 0.0216(3) Uani 1 1 d . . . C16 C 0.07152(10) 0.12579(15) 0.60301(9) 0.0217(3) Uani 1 1 d . . . H16 H 0.0147 0.0798 0.6063 0.026 Uiso 1 1 calc R . . C17 C 0.04227(10) 0.26275(16) 0.54963(9) 0.0233(3) Uani 1 1 d . . . H17 H 0.0154 0.3295 0.5796 0.028 Uiso 1 1 calc R . . C18 C 0.12884(10) 0.33329(16) 0.54102(9) 0.0263(3) Uani 1 1 d . . . H18A H 0.1085 0.4208 0.5077 0.032 Uiso 1 1 calc R . . H18B H 0.1543 0.2695 0.5093 0.032 Uiso 1 1 calc R . . C19 C 0.20907(10) 0.36980(16) 0.62835(9) 0.0249(3) Uani 1 1 d . . . C20 C 0.30084(11) 0.40039(18) 0.61264(11) 0.0343(4) Uani 1 1 d . . . H20A H 0.2905 0.4806 0.5742 0.051 Uiso 1 1 calc R . . H20B H 0.3175 0.3175 0.5873 0.051 Uiso 1 1 calc R . . H20C H 0.3519 0.4222 0.6665 0.051 Uiso 1 1 calc R . . C21 C 0.18314(12) 0.50391(16) 0.66770(11) 0.0329(4) Uani 1 1 d . . . H21A H 0.1259 0.4861 0.6782 0.049 Uiso 1 1 calc R . . H21B H 0.1726 0.5829 0.6284 0.049 Uiso 1 1 calc R . . H21C H 0.2346 0.5267 0.7211 0.049 Uiso 1 1 calc R . . C22 C 0.22877(10) 0.24043(15) 0.68997(9) 0.0240(3) Uani 1 1 d . . . H22A H 0.2670 0.1718 0.6735 0.029 Uiso 1 1 calc R . . H22B H 0.2674 0.2735 0.7477 0.029 Uiso 1 1 calc R . . O1 O 0.26988(7) 1.19675(11) 0.40613(7) 0.0299(3) Uani 1 1 d . . . O2 O 0.34246(7) 0.99011(10) 0.45834(7) 0.0243(2) Uani 1 1 d . . . O3 O 0.35351(7) 0.60284(11) 0.45857(7) 0.0314(3) Uani 1 1 d . . . H3' H 0.4038 0.5344 0.4667 0.038 Uiso 1 1 d R . . O4 O 0.55158(7) 0.66287(11) 0.51998(8) 0.0361(3) Uani 1 1 d . . . H4' H 0.6148 0.7029 0.5433 0.043 Uiso 1 1 d R . . O5 O 0.01812(8) 0.24789(12) 0.82385(7) 0.0349(3) Uani 1 1 d . . . O6 O 0.08986(7) 0.25631(10) 0.73138(6) 0.0232(2) Uani 1 1 d . . . O7 O 0.11628(7) 0.03058(11) 0.56391(7) 0.0279(3) Uani 1 1 d . . . H7' H 0.0857 -0.0618 0.5585 0.034 Uiso 1 1 d R . . O8 O -0.03045(7) 0.23029(12) 0.46697(6) 0.0297(3) Uani 1 1 d . . . H8' H -0.0108 0.2536 0.4208 0.036 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0238(7) 0.0238(8) 0.0214(7) 0.0019(6) 0.0103(6) 0.0015(6) C2 0.0207(7) 0.0266(8) 0.0260(8) 0.0013(6) 0.0068(6) -0.0001(6) C3 0.0237(7) 0.0242(8) 0.0314(8) -0.0012(6) 0.0081(6) -0.0034(6) C4 0.0209(7) 0.0159(7) 0.0313(8) 0.0016(6) 0.0110(6) -0.0027(5) C5 0.0265(8) 0.0209(7) 0.0334(8) 0.0000(6) 0.0158(7) -0.0018(6) C6 0.0215(7) 0.0172(7) 0.0459(10) -0.0005(6) 0.0166(7) 0.0005(6) C7 0.0192(7) 0.0240(8) 0.0362(9) 0.0026(6) 0.0054(6) 0.0018(6) C8 0.0259(8) 0.0236(7) 0.0289(8) 0.0027(6) 0.0091(6) 0.0025(6) C9 0.0408(10) 0.0412(10) 0.0316(9) 0.0061(7) 0.0131(8) 0.0066(8) C10 0.0309(8) 0.0268(8) 0.0349(9) -0.0038(7) 0.0067(7) 0.0007(6) C11 0.0207(7) 0.0203(7) 0.0320(8) 0.0022(6) 0.0123(6) 0.0016(6) C12 0.0251(7) 0.0318(8) 0.0186(7) -0.0008(6) 0.0089(6) -0.0041(6) C13 0.0387(9) 0.0298(8) 0.0290(8) 0.0050(7) 0.0159(7) -0.0009(7) C14 0.0317(8) 0.0260(8) 0.0256(8) 0.0036(6) 0.0114(6) 0.0035(6) C15 0.0241(7) 0.0228(7) 0.0207(7) -0.0008(6) 0.0118(6) 0.0033(6) C16 0.0207(7) 0.0265(8) 0.0215(7) -0.0019(6) 0.0120(6) -0.0013(6) C17 0.0219(7) 0.0303(8) 0.0175(7) -0.0011(6) 0.0072(6) -0.0013(6) C18 0.0287(8) 0.0300(8) 0.0223(8) 0.0022(6) 0.0122(6) -0.0036(6) C19 0.0240(7) 0.0271(8) 0.0252(8) -0.0008(6) 0.0110(6) -0.0041(6) C20 0.0304(8) 0.0375(9) 0.0390(9) -0.0008(7) 0.0176(7) -0.0089(7) C21 0.0398(9) 0.0271(8) 0.0342(9) -0.0005(7) 0.0168(7) -0.0022(7) C22 0.0200(7) 0.0283(8) 0.0233(8) -0.0024(6) 0.0079(6) -0.0006(6) O1 0.0276(6) 0.0223(6) 0.0371(6) 0.0063(5) 0.0093(5) 0.0007(4) O2 0.0198(5) 0.0192(5) 0.0326(6) 0.0045(4) 0.0087(4) -0.0009(4) O3 0.0250(5) 0.0192(5) 0.0487(7) -0.0042(5) 0.0127(5) -0.0008(4) O4 0.0229(5) 0.0251(6) 0.0649(8) -0.0071(5) 0.0219(5) 0.0006(4) O5 0.0387(6) 0.0444(7) 0.0299(6) 0.0014(5) 0.0222(5) 0.0049(5) O6 0.0278(5) 0.0253(5) 0.0204(5) 0.0013(4) 0.0136(4) 0.0028(4) O7 0.0304(6) 0.0282(6) 0.0310(6) -0.0078(4) 0.0182(5) -0.0034(4) O8 0.0254(5) 0.0426(6) 0.0187(5) 0.0018(5) 0.0057(4) -0.0053(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 1.2095(18) . ? C1 O2 1.3451(17) . ? C1 C2 1.497(2) . ? C2 C3 1.521(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.536(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O2 1.4800(16) . ? C4 C11 1.523(2) . ? C4 C5 1.528(2) . ? C5 O3 1.4192(17) . ? C5 C6 1.519(2) . ? C5 H5 0.9800 . ? C6 O4 1.4342(17) . ? C6 C7 1.515(2) . ? C6 H6 0.9800 . ? C7 C8 1.539(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.530(2) . ? C8 C10 1.535(2) . ? C8 C11 1.539(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O5 1.2077(18) . ? C12 O6 1.3397(17) . ? C12 C13 1.492(2) . ? C13 C14 1.516(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.539(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 O6 1.4771(16) . ? C15 C22 1.5190(19) . ? C15 C16 1.532(2) . ? C16 O7 1.4186(17) . ? C16 C17 1.525(2) . ? C16 H16 0.9800 . ? C17 O8 1.4347(17) . ? C17 C18 1.519(2) . ? C17 H17 0.9800 . ? C18 C19 1.541(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.533(2) . ? C19 C21 1.532(2) . ? C19 C22 1.541(2) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? O3 H3' 0.9608 . ? O4 H4' 0.9589 . ? O7 H7' 0.9648 . ? O8 H8' 0.9541 . ? 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 O2 120.96(13) . . ? O1 C1 C2 128.60(13) . . ? O2 C1 C2 110.44(12) . . ? C1 C2 C3 103.77(11) . . ? C1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? C1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? C2 C3 C4 103.16(11) . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3B 111.1 . . ? C4 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? O2 C4 C11 108.98(11) . . ? O2 C4 C5 105.75(10) . . ? C11 C4 C5 112.51(12) . . ? O2 C4 C3 102.86(11) . . ? C11 C4 C3 112.30(12) . . ? C5 C4 C3 113.66(12) . . ? O3 C5 C6 112.40(12) . . ? O3 C5 C4 105.74(11) . . ? C6 C5 C4 111.06(12) . . ? O3 C5 H5 109.2 . . ? C6 C5 H5 109.2 . . ? C4 C5 H5 109.2 . . ? O4 C6 C7 111.53(12) . . ? O4 C6 C5 107.36(12) . . ? C7 C6 C5 112.16(12) . . ? O4 C6 H6 108.6 . . ? C7 C6 H6 108.6 . . ? C5 C6 H6 108.6 . . ? C6 C7 C8 112.52(12) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C10 107.66(13) . . ? C9 C8 C7 110.06(12) . . ? C10 C8 C7 110.59(12) . . ? C9 C8 C11 107.92(12) . . ? C10 C8 C11 112.43(12) . . ? C7 C8 C11 108.14(12) . . ? 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 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C4 C11 C8 116.60(12) . . ? C4 C11 H11A 108.1 . . ? C8 C11 H11A 108.1 . . ? C4 C11 H11B 108.1 . . ? C8 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? O5 C12 O6 119.86(14) . . ? O5 C12 C13 129.12(14) . . ? O6 C12 C13 111.02(12) . . ? C12 C13 C14 105.19(12) . . ? C12 C13 H13A 110.7 . . ? C14 C13 H13A 110.7 . . ? C12 C13 H13B 110.7 . . ? C14 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? C13 C14 C15 104.92(12) . . ? C13 C14 H14A 110.8 . . ? C15 C14 H14A 110.8 . . ? C13 C14 H14B 110.8 . . ? C15 C14 H14B 110.8 . . ? H14A C14 H14B 108.8 . . ? O6 C15 C22 109.93(11) . . ? O6 C15 C16 105.42(10) . . ? C22 C15 C16 110.32(11) . . ? O6 C15 C14 104.50(11) . . ? C22 C15 C14 112.62(12) . . ? C16 C15 C14 113.60(12) . . ? O7 C16 C17 109.58(11) . . ? O7 C16 C15 108.71(11) . . ? C17 C16 C15 109.78(11) . . ? O7 C16 H16 109.6 . . ? C17 C16 H16 109.6 . . ? C15 C16 H16 109.6 . . ? O8 C17 C18 111.69(11) . . ? O8 C17 C16 109.53(12) . . ? C18 C17 C16 110.53(12) . . ? O8 C17 H17 108.3 . . ? C18 C17 H17 108.3 . . ? C16 C17 H17 108.3 . . ? C17 C18 C19 113.54(12) . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C21 108.57(12) . . ? C20 C19 C22 107.72(12) . . ? C21 C19 C22 111.43(12) . . ? C20 C19 C18 108.26(12) . . ? C21 C19 C18 110.57(13) . . ? C22 C19 C18 110.18(12) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C15 C22 C19 117.30(12) . . ? C15 C22 H22A 108.0 . . ? C19 C22 H22A 108.0 . . ? C15 C22 H22B 108.0 . . ? C19 C22 H22B 108.0 . . ? H22A C22 H22B 107.2 . . ? C1 O2 C4 110.58(10) . . ? C5 O3 H3' 109.5 . . ? C6 O4 H4' 108.2 . . ? C12 O6 C15 111.68(11) . . ? C16 O7 H7' 107.9 . . ? C17 O8 H8' 112.0 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.234 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.036 data_a11319 _database_code_depnum_ccdc_archive 'CCDC 912319' #TrackingRef 'web_deposit_cif_file_3_Chia-JungLiang_1353676544.a11319.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H42 Cl2 O8' _chemical_formula_sum 'C25 H42 Cl2 O8' _chemical_formula_weight 541.49 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0166(5) _cell_length_b 29.3472(17) _cell_length_c 10.9981(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.743(2) _cell_angle_gamma 90.00 _cell_volume 2755.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.280 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8726 _exptl_absorpt_correction_T_max 0.9725 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16410 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 24.96 _reflns_number_total 4811 _reflns_number_gt 3371 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0638P)^2^+3.0338P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4811 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0862 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1537 _refine_ls_wR_factor_gt 0.1360 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.8713(3) 0.53564(10) 0.5521(3) 0.0261(7) Uani 1 1 d . . . C2 C 1.0016(4) 0.56047(11) 0.6495(3) 0.0387(8) Uani 1 1 d . . . H2A H 0.9826 0.5936 0.6369 0.046 Uiso 1 1 calc R . . H2B H 1.1009 0.5536 0.6329 0.046 Uiso 1 1 calc R . . C3 C 1.0220(4) 0.54907(10) 0.7884(3) 0.0324(7) Uani 1 1 d . . . H3A H 0.9407 0.5647 0.8158 0.039 Uiso 1 1 calc R . . H3B H 1.1260 0.5594 0.8443 0.039 Uiso 1 1 calc R . . C4 C 1.0075(3) 0.49776(10) 0.8000(3) 0.0273(7) Uani 1 1 d . . . H4A H 1.0905 0.4826 0.7738 0.033 Uiso 1 1 calc R . . H4B H 1.0238 0.4898 0.8909 0.033 Uiso 1 1 calc R . . C5 C 0.8488(3) 0.48011(9) 0.7177(3) 0.0225(6) Uani 1 1 d . . . C6 C 0.7142(3) 0.49523(9) 0.7667(3) 0.0207(6) Uani 1 1 d . . . H6 H 0.7028 0.5291 0.7593 0.025 Uiso 1 1 calc R . . C7 C 0.5600(3) 0.47302(9) 0.6896(3) 0.0211(6) Uani 1 1 d . . . H7 H 0.5317 0.4830 0.5980 0.025 Uiso 1 1 calc R . . C8 C 0.5722(3) 0.42150(9) 0.6958(3) 0.0244(6) Uani 1 1 d . . . H8A H 0.4695 0.4083 0.6465 0.029 Uiso 1 1 calc R . . H8B H 0.5969 0.4117 0.7862 0.029 Uiso 1 1 calc R . . C9 C 0.6979(3) 0.40275(9) 0.6423(3) 0.0255(7) Uani 1 1 d . . . C10 C 0.7248(4) 0.35207(10) 0.6793(3) 0.0349(8) Uani 1 1 d . . . H10A H 0.7582 0.3491 0.7730 0.052 Uiso 1 1 calc R . . H10B H 0.8063 0.3398 0.6472 0.052 Uiso 1 1 calc R . . H10C H 0.6272 0.3351 0.6413 0.052 Uiso 1 1 calc R . . C11 C 0.6456(4) 0.40609(10) 0.4955(3) 0.0326(7) Uani 1 1 d . . . H11A H 0.5471 0.3894 0.4588 0.049 Uiso 1 1 calc R . . H11B H 0.7262 0.3928 0.4641 0.049 Uiso 1 1 calc R . . H11C H 0.6300 0.4382 0.4697 0.049 Uiso 1 1 calc R . . C12 C 0.8528(3) 0.42811(9) 0.7065(3) 0.0257(7) Uani 1 1 d . . . H12A H 0.8989 0.4156 0.7943 0.031 Uiso 1 1 calc R . . H12B H 0.9254 0.4205 0.6585 0.031 Uiso 1 1 calc R . . C13 C 0.5651(4) 0.28779(10) -0.1013(3) 0.0309(7) Uani 1 1 d . . . C14 C 0.7015(4) 0.26432(11) -0.0069(3) 0.0397(8) Uani 1 1 d . . . H14A H 0.7974 0.2724 -0.0274 0.048 Uiso 1 1 calc R . . H14B H 0.6863 0.2310 -0.0187 0.048 Uiso 1 1 calc R . . C15 C 0.7282(4) 0.27549(11) 0.1340(3) 0.0382(8) Uani 1 1 d . . . H15A H 0.6523 0.2585 0.1647 0.046 Uiso 1 1 calc R . . H15B H 0.8351 0.2661 0.1863 0.046 Uiso 1 1 calc R . . C16 C 0.7083(4) 0.32648(10) 0.1496(3) 0.0323(7) Uani 1 1 d . . . H16A H 0.7922 0.3431 0.1282 0.039 Uiso 1 1 calc R . . H16B H 0.7191 0.3331 0.2403 0.039 Uiso 1 1 calc R . . C17 C 0.5493(3) 0.34340(9) 0.0635(3) 0.0231(6) Uani 1 1 d . . . C18 C 0.5460(3) 0.39553(9) 0.0538(3) 0.0228(6) Uani 1 1 d . . . H18 H 0.6270 0.4056 0.0151 0.027 Uiso 1 1 calc R . . C19 C 0.3864(3) 0.41288(9) -0.0293(3) 0.0218(6) Uani 1 1 d . . . H19 H 0.3644 0.4017 -0.1192 0.026 Uiso 1 1 calc R . . C20 C 0.2579(3) 0.39678(9) 0.0217(3) 0.0256(7) Uani 1 1 d . . . H20A H 0.1561 0.4086 -0.0345 0.031 Uiso 1 1 calc R . . H20B H 0.2766 0.4096 0.1086 0.031 Uiso 1 1 calc R . . C21 C 0.2482(3) 0.34455(10) 0.0289(3) 0.0284(7) Uani 1 1 d . . . C22 C 0.1353(4) 0.33221(12) 0.1027(4) 0.0458(9) Uani 1 1 d . . . H22A H 0.0305 0.3438 0.0561 0.069 Uiso 1 1 calc R . . H22B H 0.1723 0.3459 0.1885 0.069 Uiso 1 1 calc R . . H22C H 0.1311 0.2990 0.1107 0.069 Uiso 1 1 calc R . . C23 C 0.1814(4) 0.32389(11) -0.1068(3) 0.0392(8) Uani 1 1 d . . . H23A H 0.2514 0.3310 -0.1564 0.059 Uiso 1 1 calc R . . H23B H 0.0775 0.3368 -0.1501 0.059 Uiso 1 1 calc R . . H23C H 0.1729 0.2908 -0.1001 0.059 Uiso 1 1 calc R . . C24 C 0.4123(3) 0.32564(10) 0.1044(3) 0.0261(7) Uani 1 1 d . . . H24A H 0.4341 0.3329 0.1964 0.031 Uiso 1 1 calc R . . H24B H 0.4091 0.2920 0.0960 0.031 Uiso 1 1 calc R . . C25 C 0.2277(5) 0.32300(15) 0.5609(4) 0.0607(11) Uani 1 1 d . . . H25A H 0.2793 0.3075 0.6437 0.073 Uiso 1 1 calc R . . H25B H 0.2389 0.3563 0.5755 0.073 Uiso 1 1 calc R . . Cl1 Cl 0.32100(14) 0.30693(5) 0.44914(11) 0.0775(4) Uani 1 1 d . . . Cl2 Cl 0.02934(14) 0.30879(5) 0.50662(16) 0.0881(5) Uani 1 1 d . . . O1 O 0.8068(2) 0.49847(6) 0.58449(18) 0.0252(5) Uani 1 1 d . . . O2 O 0.8229(2) 0.54727(7) 0.4395(2) 0.0359(5) Uani 1 1 d . . . O3 O 0.7562(2) 0.48254(7) 0.89819(18) 0.0278(5) Uani 1 1 d . . . H3' H 0.8416 0.4949 0.9393 0.042 Uiso 1 1 calc R . . O4 O 0.4417(2) 0.48933(6) 0.74299(18) 0.0242(5) Uani 1 1 d . . . H4' H 0.3544 0.4780 0.7018 0.036 Uiso 1 1 calc R . . O5 O 0.5235(2) 0.32943(6) -0.07101(19) 0.0282(5) Uani 1 1 d . . . O6 O 0.4969(3) 0.27329(7) -0.2073(2) 0.0427(6) Uani 1 1 d . . . O7 O 0.5871(2) 0.41237(7) 0.18190(18) 0.0308(5) Uani 1 1 d . . . H7' H 0.5145 0.4289 0.1893 0.046 Uiso 1 1 calc R . . O8 O 0.3903(2) 0.46207(6) -0.02839(18) 0.0268(5) Uani 1 1 d . . . H8' H 0.3079 0.4722 -0.0183 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0229(16) 0.0308(16) 0.0267(18) -0.0002(13) 0.0107(13) -0.0019(13) C2 0.0360(19) 0.0384(18) 0.036(2) 0.0019(15) 0.0037(16) -0.0150(15) C3 0.0247(16) 0.0386(18) 0.0311(18) -0.0081(14) 0.0051(14) -0.0096(14) C4 0.0241(16) 0.0350(16) 0.0201(16) -0.0011(13) 0.0036(13) -0.0006(13) C5 0.0220(15) 0.0275(15) 0.0162(15) 0.0018(12) 0.0039(12) -0.0004(12) C6 0.0240(15) 0.0205(14) 0.0160(15) -0.0001(11) 0.0041(12) 0.0003(12) C7 0.0216(15) 0.0270(15) 0.0157(14) 0.0000(11) 0.0076(12) 0.0009(12) C8 0.0252(16) 0.0270(15) 0.0222(16) 0.0008(12) 0.0090(13) -0.0020(12) C9 0.0281(16) 0.0224(14) 0.0270(17) -0.0008(12) 0.0102(13) -0.0016(12) C10 0.0390(19) 0.0237(15) 0.045(2) -0.0012(14) 0.0169(16) -0.0006(14) C11 0.0400(19) 0.0329(17) 0.0270(17) -0.0084(13) 0.0136(15) -0.0092(14) C12 0.0246(16) 0.0269(15) 0.0265(16) -0.0001(12) 0.0094(13) 0.0031(12) C13 0.0369(18) 0.0246(15) 0.039(2) -0.0011(14) 0.0225(16) -0.0001(14) C14 0.040(2) 0.0304(17) 0.055(2) 0.0032(16) 0.0235(18) 0.0083(15) C15 0.0338(19) 0.0342(17) 0.046(2) 0.0118(15) 0.0125(16) 0.0100(15) C16 0.0271(17) 0.0350(17) 0.0320(18) 0.0036(14) 0.0057(14) 0.0055(14) C17 0.0239(15) 0.0263(15) 0.0205(15) 0.0005(12) 0.0087(13) 0.0009(12) C18 0.0233(15) 0.0249(15) 0.0214(15) -0.0004(12) 0.0088(13) -0.0019(12) C19 0.0272(16) 0.0196(14) 0.0195(15) -0.0002(11) 0.0090(13) 0.0001(12) C20 0.0226(15) 0.0263(15) 0.0294(17) 0.0012(12) 0.0102(13) 0.0017(12) C21 0.0251(16) 0.0264(15) 0.0360(18) 0.0030(13) 0.0131(14) -0.0003(13) C22 0.037(2) 0.041(2) 0.068(3) 0.0108(18) 0.0289(19) -0.0035(16) C23 0.0305(18) 0.0320(17) 0.048(2) -0.0075(15) 0.0031(16) -0.0017(14) C24 0.0284(17) 0.0235(14) 0.0280(17) 0.0050(12) 0.0110(14) 0.0012(12) C25 0.050(3) 0.073(3) 0.052(3) -0.003(2) 0.007(2) -0.005(2) Cl1 0.0648(7) 0.1172(10) 0.0533(7) -0.0016(7) 0.0228(6) -0.0277(7) Cl2 0.0485(7) 0.0852(9) 0.1325(13) -0.0148(8) 0.0319(7) -0.0088(6) O1 0.0254(11) 0.0305(11) 0.0185(11) 0.0012(8) 0.0052(9) -0.0069(9) O2 0.0321(12) 0.0466(13) 0.0267(13) 0.0078(10) 0.0060(10) -0.0091(10) O3 0.0240(11) 0.0407(12) 0.0146(10) -0.0024(9) 0.0005(9) -0.0002(9) O4 0.0201(10) 0.0299(10) 0.0234(11) -0.0019(8) 0.0084(9) 0.0000(8) O5 0.0352(12) 0.0255(10) 0.0250(12) -0.0004(9) 0.0115(10) 0.0058(9) O6 0.0547(16) 0.0367(13) 0.0398(15) -0.0115(11) 0.0193(13) 0.0031(11) O7 0.0335(12) 0.0338(11) 0.0213(11) -0.0039(9) 0.0036(9) 0.0027(9) O8 0.0330(12) 0.0200(10) 0.0311(12) 0.0013(9) 0.0154(10) 0.0041(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.223(3) . ? C1 O1 1.337(3) . ? C1 C2 1.500(4) . ? C2 C3 1.517(4) . ? 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 O1 1.491(3) . ? C5 C12 1.532(4) . ? C5 C6 1.543(4) . ? C6 O3 1.422(3) . ? C6 C7 1.522(4) . ? C6 H6 1.0000 . ? C7 O4 1.454(3) . ? C7 C8 1.516(4) . ? C7 H7 1.0000 . ? C8 C9 1.536(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C11 1.533(4) . ? C9 C12 1.540(4) . ? C9 C10 1.541(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O6 1.207(4) . ? C13 O5 1.351(3) . ? C13 C14 1.498(5) . ? C14 C15 1.525(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.523(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.525(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 O5 1.480(3) . ? C17 C18 1.533(4) . ? C17 C24 1.535(4) . ? C18 O7 1.425(3) . ? C18 C19 1.523(4) . ? C18 H18 1.0000 . ? C19 O8 1.444(3) . ? C19 C20 1.516(4) . ? C19 H19 1.0000 . ? C20 C21 1.539(4) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.535(4) . ? C21 C23 1.543(4) . ? C21 C24 1.548(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 Cl2 1.745(4) . ? C25 Cl1 1.762(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? O3 H3' 0.8400 . ? O4 H4' 0.8400 . ? O7 H7' 0.8400 . ? O8 H8' 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 117.0(3) . . ? O2 C1 C2 122.0(3) . . ? O1 C1 C2 121.0(3) . . ? C1 C2 C3 115.2(3) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 108.5(3) . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? C5 C4 C3 112.2(2) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? O1 C5 C4 110.9(2) . . ? O1 C5 C12 106.6(2) . . ? C4 C5 C12 110.2(2) . . ? O1 C5 C6 105.0(2) . . ? C4 C5 C6 113.0(2) . . ? C12 C5 C6 110.8(2) . . ? O3 C6 C7 110.5(2) . . ? O3 C6 C5 107.3(2) . . ? C7 C6 C5 111.3(2) . . ? O3 C6 H6 109.2 . . ? C7 C6 H6 109.2 . . ? C5 C6 H6 109.2 . . ? O4 C7 C8 111.3(2) . . ? O4 C7 C6 107.0(2) . . ? C8 C7 C6 111.2(2) . . ? O4 C7 H7 109.1 . . ? C8 C7 H7 109.1 . . ? C6 C7 H7 109.1 . . ? C7 C8 C9 113.1(2) . . ? 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 . . ? C11 C9 C8 111.4(2) . . ? C11 C9 C12 112.3(2) . . ? C8 C9 C12 108.8(2) . . ? C11 C9 C10 108.0(2) . . ? C8 C9 C10 108.5(2) . . ? C12 C9 C10 107.6(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 C9 118.5(2) . . ? C5 C12 H12A 107.7 . . ? C9 C12 H12A 107.7 . . ? C5 C12 H12B 107.7 . . ? C9 C12 H12B 107.7 . . ? H12A C12 H12B 107.1 . . ? O6 C13 O5 117.5(3) . . ? O6 C13 C14 123.8(3) . . ? O5 C13 C14 118.4(3) . . ? C13 C14 C15 115.6(3) . . ? C13 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? C13 C14 H14B 108.4 . . ? C15 C14 H14B 108.4 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C14 109.9(3) . . ? C16 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? C16 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C15 C16 C17 111.8(3) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? O5 C17 C16 110.2(2) . . ? O5 C17 C18 102.3(2) . . ? C16 C17 C18 111.2(2) . . ? O5 C17 C24 108.4(2) . . ? C16 C17 C24 113.1(2) . . ? C18 C17 C24 111.1(2) . . ? O7 C18 C19 111.9(2) . . ? O7 C18 C17 106.5(2) . . ? C19 C18 C17 111.6(2) . . ? O7 C18 H18 108.9 . . ? C19 C18 H18 108.9 . . ? C17 C18 H18 108.9 . . ? O8 C19 C20 109.2(2) . . ? O8 C19 C18 108.3(2) . . ? C20 C19 C18 111.2(2) . . ? O8 C19 H19 109.4 . . ? C20 C19 H19 109.4 . . ? C18 C19 H19 109.4 . . ? C19 C20 C21 113.1(2) . . ? C19 C20 H20A 109.0 . . ? C21 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C20 108.7(2) . . ? C22 C21 C23 107.4(3) . . ? C20 C21 C23 110.7(3) . . ? C22 C21 C24 108.3(3) . . ? C20 C21 C24 108.9(2) . . ? C23 C21 C24 112.7(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C17 C24 C21 116.2(2) . . ? C17 C24 H24A 108.2 . . ? C21 C24 H24A 108.2 . . ? C17 C24 H24B 108.2 . . ? C21 C24 H24B 108.2 . . ? H24A C24 H24B 107.4 . . ? Cl2 C25 Cl1 111.4(2) . . ? Cl2 C25 H25A 109.4 . . ? Cl1 C25 H25A 109.4 . . ? Cl2 C25 H25B 109.4 . . ? Cl1 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C1 O1 C5 124.1(2) . . ? C6 O3 H3' 109.5 . . ? C7 O4 H4' 109.5 . . ? C13 O5 C17 122.0(2) . . ? C18 O7 H7' 109.5 . . ? C19 O8 H8' 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.026 _refine_diff_density_min -0.832 _refine_diff_density_rms 0.057 data_a11263 _database_code_depnum_ccdc_archive 'CCDC 912320' #TrackingRef 'web_deposit_cif_file_4_Chia-JungLiang_1353676544.a11263.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 O4' _chemical_formula_sum 'C10 H16 O4' _chemical_formula_weight 200.23 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 9.3155(11) _cell_length_b 19.012(2) _cell_length_c 6.3222(7) _cell_angle_alpha 90.00 _cell_angle_beta 118.966(2) _cell_angle_gamma 90.00 _cell_volume 979.64(19) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9546 _exptl_absorpt_correction_T_max 0.9897 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2283 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 24.88 _reflns_number_total 1427 _reflns_number_gt 1286 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0652P)^2^+0.1602P] 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 fixed _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 1.3(14) _refine_ls_number_reflns 1427 _refine_ls_number_parameters 127 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0993 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.5691(3) 0.09344(13) 0.5021(5) 0.0275(6) Uani 1 1 d . . . C2 C 0.4790(4) 0.10556(16) 0.6402(5) 0.0363(7) Uani 1 1 d . . . H2A H 0.4432 0.0595 0.6711 0.044 Uiso 1 1 calc R . . H2B H 0.3791 0.1333 0.5379 0.044 Uiso 1 1 calc R . . C3 C 0.5763(4) 0.14340(17) 0.8802(5) 0.0371(7) Uani 1 1 d . . . H3A H 0.5233 0.1365 0.9818 0.044 Uiso 1 1 calc R . . H3B H 0.5795 0.1945 0.8523 0.044 Uiso 1 1 calc R . . C4 C 0.7501(3) 0.11369(17) 1.0081(5) 0.0351(7) Uani 1 1 d . . . H4A H 0.7455 0.0626 1.0345 0.042 Uiso 1 1 calc R . . H4B H 0.8131 0.1364 1.1681 0.042 Uiso 1 1 calc R . . C5 C 0.8370(3) 0.12589(14) 0.8604(4) 0.0262(6) Uani 1 1 d . . . C6 C 0.9854(3) 0.07769(14) 0.9372(5) 0.0275(6) Uani 1 1 d . . . H6 H 0.9476 0.0277 0.9143 0.033 Uiso 1 1 calc R . . C7 C 1.0739(3) 0.09077(14) 0.7915(5) 0.0278(6) Uani 1 1 d . . . H7 H 0.9949 0.0806 0.6180 0.033 Uiso 1 1 calc R . . C8 C 1.1274(4) 0.16690(14) 0.8085(5) 0.0330(7) Uani 1 1 d . . . H8A H 1.1792 0.1742 0.7056 0.040 Uiso 1 1 calc R . . H8B H 1.2097 0.1779 0.9776 0.040 Uiso 1 1 calc R . . C9 C 0.9810(4) 0.21589(15) 0.7271(5) 0.0350(7) Uani 1 1 d . . . H9A H 0.9057 0.2088 0.5524 0.042 Uiso 1 1 calc R . . H9B H 1.0196 0.2653 0.7511 0.042 Uiso 1 1 calc R . . C10 C 0.8884(3) 0.20287(15) 0.8671(5) 0.0320(7) Uani 1 1 d . . . H10A H 0.7890 0.2328 0.7985 0.038 Uiso 1 1 calc R . . H10B H 0.9587 0.2171 1.0375 0.038 Uiso 1 1 calc R . . O1 O 0.5027(3) 0.07244(11) 0.2965(3) 0.0402(5) Uani 1 1 d . . . O2 O 0.7304(2) 0.10701(10) 0.6037(3) 0.0309(5) Uani 1 1 d . . . O3 O 1.0926(3) 0.08985(10) 1.1883(3) 0.0361(5) Uani 1 1 d . . . H3 H 1.1755 0.0639 1.2365 0.054 Uiso 1 1 calc R . . O4 O 1.2099(2) 0.04371(10) 0.8662(3) 0.0348(5) Uani 1 1 d . . . H4 H 1.1751 0.0025 0.8249 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0237(15) 0.0274(13) 0.0251(15) 0.0037(11) 0.0068(12) -0.0040(12) C2 0.0260(16) 0.0427(17) 0.0376(17) 0.0029(13) 0.0134(14) -0.0049(13) C3 0.0333(16) 0.0483(19) 0.0344(16) 0.0008(13) 0.0201(13) -0.0003(15) C4 0.0318(17) 0.0477(19) 0.0226(15) 0.0048(12) 0.0104(13) 0.0003(13) C5 0.0246(15) 0.0307(14) 0.0178(12) -0.0016(11) 0.0059(11) -0.0031(13) C6 0.0267(14) 0.0249(14) 0.0189(13) -0.0008(10) 0.0015(11) -0.0020(11) C7 0.0205(14) 0.0276(14) 0.0236(14) -0.0042(11) 0.0014(11) 0.0024(11) C8 0.0278(15) 0.0317(15) 0.0379(16) -0.0013(12) 0.0146(13) -0.0007(13) C9 0.0349(17) 0.0285(15) 0.0401(16) 0.0048(12) 0.0170(14) -0.0011(12) C10 0.0320(17) 0.0238(14) 0.0348(15) 0.0014(12) 0.0120(13) 0.0035(12) O1 0.0310(11) 0.0520(14) 0.0272(11) -0.0061(10) 0.0059(9) -0.0066(11) O2 0.0197(10) 0.0466(11) 0.0194(9) -0.0018(8) 0.0038(8) -0.0017(9) O3 0.0343(12) 0.0358(11) 0.0222(10) -0.0008(8) 0.0012(9) 0.0065(9) O4 0.0277(11) 0.0291(10) 0.0360(10) -0.0093(9) 0.0063(8) 0.0051(9) _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 1.205(3) . ? C1 O2 1.343(3) . ? C1 C2 1.493(4) . ? C2 C3 1.520(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.525(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.521(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O2 1.479(3) . ? C5 C6 1.528(4) . ? C5 C10 1.534(4) . ? C6 O3 1.426(3) . ? C6 C7 1.525(4) . ? C6 H6 1.0000 . ? C7 O4 1.432(3) . ? C7 C8 1.517(4) . ? C7 H7 1.0000 . ? C8 C9 1.520(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.526(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? O3 H3 0.8400 . ? O4 H4 0.8400 . ? 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 O2 116.8(2) . . ? O1 C1 C2 122.8(3) . . ? O2 C1 C2 120.4(2) . . ? C1 C2 C3 115.1(2) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 108.7(2) . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.3 . . ? C3 C4 C5 111.2(2) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? O2 C5 C4 111.2(2) . . ? O2 C5 C6 103.10(19) . . ? C4 C5 C6 112.5(2) . . ? O2 C5 C10 107.24(19) . . ? C4 C5 C10 112.4(2) . . ? C6 C5 C10 110.0(2) . . ? O3 C6 C5 107.1(2) . . ? O3 C6 C7 110.8(2) . . ? C5 C6 C7 112.4(2) . . ? O3 C6 H6 108.8 . . ? C5 C6 H6 108.8 . . ? C7 C6 H6 108.8 . . ? O4 C7 C8 111.4(2) . . ? O4 C7 C6 110.5(2) . . ? C8 C7 C6 111.6(2) . . ? O4 C7 H7 107.7 . . ? C8 C7 H7 107.7 . . ? C6 C7 H7 107.7 . . ? C7 C8 C9 110.5(2) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 111.7(2) . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? C9 C10 C5 113.3(2) . . ? C9 C10 H10A 108.9 . . ? C5 C10 H10A 108.9 . . ? C9 C10 H10B 108.9 . . ? C5 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C1 O2 C5 124.95(19) . . ? C6 O3 H3 109.5 . . ? C7 O4 H4 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.88 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.294 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.038 data_10236 _database_code_depnum_ccdc_archive 'CCDC 912989' #TrackingRef 'web_deposit_cif_file_0_Chia-JungLiang_1354091839.10236.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 O5 S' _chemical_formula_sum 'C16 H22 O5 S' _chemical_formula_weight 326.40 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.9020(2) _cell_length_b 34.8990(12) _cell_length_c 7.9480(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.6710(10) _cell_angle_gamma 90.00 _cell_volume 1608.77(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7792 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7566 _exptl_absorpt_correction_T_max 1.2634 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3977 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 2 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2363 _reflns_number_gt 1869 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1300P)^2^+0.4960P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2363 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1960 _refine_ls_wR_factor_gt 0.1767 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.4185(6) 0.07178(10) 0.3892(4) 0.0426(8) Uani 1 1 d . . . C2 C 0.6304(6) 0.05467(11) 0.3983(5) 0.0533(9) Uani 1 1 d . . . H2 H 0.7027 0.0545 0.3038 0.064 Uiso 1 1 calc R . . C3 C 0.7343(7) 0.03771(12) 0.5514(5) 0.0607(10) Uani 1 1 d . . . H3 H 0.8764 0.0257 0.5580 0.073 Uiso 1 1 calc R . . C4 C 0.6317(7) 0.03822(11) 0.6937(5) 0.0576(10) Uani 1 1 d . . . C5 C 0.7536(9) 0.02150(15) 0.8617(6) 0.0862(15) Uani 1 1 d . . . H5A H 0.8997 0.0112 0.8478 0.129 Uiso 1 1 calc R . . H5B H 0.6608 0.0015 0.8967 0.129 Uiso 1 1 calc R . . H5C H 0.7775 0.0412 0.9474 0.129 Uiso 1 1 calc R . . C6 C 0.4194(7) 0.05514(11) 0.6800(4) 0.0587(10) Uani 1 1 d . . . H6 H 0.3474 0.0554 0.7746 0.070 Uiso 1 1 calc R . . C7 C 0.3107(6) 0.07173(11) 0.5307(4) 0.0512(9) Uani 1 1 d . . . H7 H 0.1661 0.0829 0.5239 0.061 Uiso 1 1 calc R . . C8 C 0.5373(5) 0.15627(10) 0.3264(4) 0.0367(7) Uani 1 1 d . . . H8 H 0.6566 0.1371 0.3199 0.044 Uiso 1 1 calc R . . C9 C 0.5653(6) 0.18981(11) 0.2131(4) 0.0460(8) Uani 1 1 d . . . H9A H 0.4402 0.2079 0.2127 0.055 Uiso 1 1 calc R . . H9B H 0.5606 0.1811 0.0967 0.055 Uiso 1 1 calc R . . C10 C 0.7952(6) 0.20922(11) 0.2803(4) 0.0493(9) Uani 1 1 d . . . H10A H 0.8101 0.2318 0.2121 0.059 Uiso 1 1 calc R . . H10B H 0.9200 0.1918 0.2695 0.059 Uiso 1 1 calc R . . C11 C 0.8140(6) 0.22080(10) 0.4677(4) 0.0422(8) Uani 1 1 d . . . H11A H 0.9658 0.2315 0.5086 0.051 Uiso 1 1 calc R . . H11B H 0.7014 0.2407 0.4755 0.051 Uiso 1 1 calc R . . C12 C 0.7754(5) 0.18782(9) 0.5826(4) 0.0358(7) Uani 1 1 d . . . C13 C 0.5451(5) 0.16790(9) 0.5114(4) 0.0358(7) Uani 1 1 d . . . H13 H 0.5290 0.1451 0.5800 0.043 Uiso 1 1 calc R . . C14 C 0.7921(6) 0.19836(11) 0.7715(4) 0.0477(9) Uani 1 1 d . . . H14A H 0.8630 0.2233 0.7949 0.057 Uiso 1 1 calc R . . H14B H 0.6402 0.1989 0.8017 0.057 Uiso 1 1 calc R . . C15 C 0.9316(16) 0.1693(2) 0.8659(6) 0.180(5) Uani 1 1 d . . . H15A H 1.0590 0.1811 0.9431 0.216 Uiso 1 1 calc R . . H15B H 0.8404 0.1550 0.9342 0.216 Uiso 1 1 calc R . . C16 C 1.0199(7) 0.14354(13) 0.7521(4) 0.0617(11) Uani 1 1 d . . . H16A H 0.9534 0.1182 0.7566 0.074 Uiso 1 1 calc R . . H16B H 1.1863 0.1415 0.7840 0.074 Uiso 1 1 calc R . . O1 O 0.0469(5) 0.08903(9) 0.1708(4) 0.0747(9) Uani 1 1 d . . . O2 O 0.4191(5) 0.09108(9) 0.0753(3) 0.0731(9) Uani 1 1 d . . . O3 O 0.3058(4) 0.13952(7) 0.2655(3) 0.0458(6) Uani 1 1 d . . . O4 O 0.3670(3) 0.19428(7) 0.5258(3) 0.0485(6) Uani 1 1 d . . . H4 H 0.2931 0.1991 0.4303 0.073 Uiso 1 1 calc R . . O5 O 0.9562(3) 0.15955(7) 0.5822(2) 0.0398(6) Uani 1 1 d . . . S1 S 0.28726(15) 0.09663(3) 0.20571(10) 0.0507(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 0.053(2) 0.0399(19) 0.0327(17) -0.0066(13) 0.0009(14) -0.0025(15) C2 0.058(2) 0.053(2) 0.051(2) -0.0061(17) 0.0144(16) -0.0022(17) C3 0.055(2) 0.054(3) 0.067(3) -0.0005(19) -0.0019(19) 0.0070(18) C4 0.072(2) 0.047(2) 0.047(2) -0.0026(16) -0.0080(18) -0.0059(19) C5 0.108(4) 0.074(3) 0.062(3) 0.014(2) -0.020(2) -0.003(3) C6 0.077(3) 0.060(3) 0.0389(19) -0.0005(17) 0.0092(17) -0.001(2) C7 0.050(2) 0.056(2) 0.0470(19) -0.0032(17) 0.0077(16) 0.0025(17) C8 0.0332(15) 0.0449(19) 0.0298(14) 0.0003(13) -0.0004(12) -0.0008(13) C9 0.0507(19) 0.056(2) 0.0302(16) 0.0075(15) 0.0034(13) 0.0005(16) C10 0.051(2) 0.057(2) 0.0405(18) 0.0099(16) 0.0085(14) -0.0057(17) C11 0.0388(17) 0.042(2) 0.0442(18) -0.0008(14) 0.0040(14) -0.0032(14) C12 0.0315(15) 0.0428(19) 0.0321(15) -0.0027(13) 0.0039(11) 0.0038(13) C13 0.0344(16) 0.0426(19) 0.0306(14) 0.0019(13) 0.0064(12) -0.0004(13) C14 0.0472(18) 0.058(2) 0.0364(17) -0.0114(16) 0.0041(13) -0.0010(16) C15 0.285(9) 0.212(8) 0.032(2) 0.000(3) 0.002(4) 0.188(8) C16 0.071(2) 0.077(3) 0.0352(17) 0.0125(18) 0.0054(16) 0.027(2) O1 0.0635(17) 0.078(2) 0.0688(18) -0.0006(15) -0.0234(14) -0.0229(15) O2 0.106(2) 0.079(2) 0.0333(14) -0.0112(13) 0.0126(14) 0.0020(17) O3 0.0400(12) 0.0491(15) 0.0422(12) -0.0029(10) -0.0083(9) -0.0047(11) O4 0.0357(12) 0.0611(16) 0.0480(13) -0.0086(11) 0.0061(9) 0.0069(11) O5 0.0351(11) 0.0535(15) 0.0301(10) 0.0012(9) 0.0045(8) 0.0073(10) S1 0.0591(6) 0.0531(6) 0.0337(5) -0.0057(4) -0.0074(4) -0.0075(4) _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 C2 1.375(5) . ? C1 C7 1.391(5) . ? C1 S1 1.750(3) . ? C2 C3 1.389(5) . ? C2 H2 0.9300 . ? C3 C4 1.378(6) . ? C3 H3 0.9300 . ? C4 C6 1.371(6) . ? C4 C5 1.511(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.368(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O3 1.483(3) . ? C8 C9 1.505(5) . ? C8 C13 1.518(4) . ? C8 H8 0.9800 . ? C9 C10 1.522(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.528(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.512(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O5 1.454(3) . ? C12 C14 1.531(4) . ? C12 C13 1.538(4) . ? C13 O4 1.418(4) . ? C13 H13 0.9800 . ? C14 C15 1.430(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.439(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 O5 1.445(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? O1 S1 1.419(3) . ? O2 S1 1.420(3) . ? O3 S1 1.568(3) . ? O4 H4 0.8200 . ? 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 C2 C1 C7 120.3(3) . . ? C2 C1 S1 121.1(3) . . ? C7 C1 S1 118.4(3) . . ? C1 C2 C3 118.7(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 121.6(4) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C6 C4 C3 118.3(3) . . ? C6 C4 C5 121.0(4) . . ? C3 C4 C5 120.7(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C4 121.8(3) . . ? C7 C6 H6 119.1 . . ? C4 C6 H6 119.1 . . ? C6 C7 C1 119.3(3) . . ? C6 C7 H7 120.3 . . ? C1 C7 H7 120.3 . . ? O3 C8 C9 107.9(2) . . ? O3 C8 C13 106.4(2) . . ? C9 C8 C13 112.6(3) . . ? O3 C8 H8 109.9 . . ? C9 C8 H8 109.9 . . ? C13 C8 H8 109.9 . . ? C8 C9 C10 109.0(3) . . ? C8 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? C8 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C9 C10 C11 111.0(3) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 113.3(3) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? O5 C12 C11 108.8(2) . . ? O5 C12 C14 104.5(2) . . ? C11 C12 C14 114.8(3) . . ? O5 C12 C13 106.9(3) . . ? C11 C12 C13 110.1(2) . . ? C14 C12 C13 111.2(2) . . ? O4 C13 C8 111.2(2) . . ? O4 C13 C12 107.1(2) . . ? C8 C13 C12 110.1(2) . . ? O4 C13 H13 109.4 . . ? C8 C13 H13 109.4 . . ? C12 C13 H13 109.4 . . ? C15 C14 C12 105.7(3) . . ? C15 C14 H14A 110.6 . . ? C12 C14 H14A 110.6 . . ? C15 C14 H14B 110.6 . . ? C12 C14 H14B 110.6 . . ? H14A C14 H14B 108.7 . . ? C16 C15 C14 110.7(4) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 O5 106.5(3) . . ? C15 C16 H16A 110.4 . . ? O5 C16 H16A 110.4 . . ? C15 C16 H16B 110.4 . . ? O5 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? C8 O3 S1 118.91(19) . . ? C13 O4 H4 109.5 . . ? C16 O5 C12 108.9(2) . . ? O2 S1 O1 119.68(18) . . ? O2 S1 O3 109.56(16) . . ? O1 S1 O3 104.39(16) . . ? O2 S1 C1 108.83(17) . . ? O1 S1 C1 110.03(17) . . ? O3 S1 C1 103.01(13) . . ? _diffrn_measured_fraction_theta_max 0.829 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.829 _refine_diff_density_max 0.407 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.112 data_a9855 _database_code_depnum_ccdc_archive 'CCDC 912990' #TrackingRef 'web_deposit_cif_file_1_Chia-JungLiang_1354091839.a9855.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H23 N O4 S' _chemical_formula_sum 'C16 H23 N O4 S' _chemical_formula_weight 325.41 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' N N 0.0061 0.0033 '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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.8290(4) _cell_length_b 9.8991(4) _cell_length_c 16.3718(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1592.95(11) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8518 _exptl_absorpt_correction_T_max 0.9367 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11494 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2785 _reflns_number_gt 2639 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0534P)^2^+0.4240P] 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 fixed _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 0.45(7) _refine_ls_number_reflns 2785 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0880 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.1060(2) 0.6681(2) 0.21432(13) 0.0241(5) Uani 1 1 d . . . C2 C 0.0067(2) 0.7595(2) 0.19105(14) 0.0319(5) Uani 1 1 d . . . H2 H -0.0393 0.8119 0.2311 0.038 Uiso 1 1 calc R . . C3 C -0.0251(3) 0.7741(2) 0.10947(15) 0.0348(6) Uani 1 1 d . . . H3 H -0.0921 0.8380 0.0937 0.042 Uiso 1 1 calc R . . C4 C 0.0391(2) 0.6971(2) 0.04998(14) 0.0300(5) Uani 1 1 d . . . C5 C -0.0016(3) 0.7088(3) -0.03813(15) 0.0452(7) Uani 1 1 d . . . H5A H 0.0536 0.6469 -0.0711 0.068 Uiso 1 1 calc R . . H5B H 0.0131 0.8017 -0.0568 0.068 Uiso 1 1 calc R . . H5C H -0.0980 0.6855 -0.0440 0.068 Uiso 1 1 calc R . . C6 C 0.1380(2) 0.6059(2) 0.07465(13) 0.0307(5) Uani 1 1 d . . . H6 H 0.1831 0.5525 0.0348 0.037 Uiso 1 1 calc R . . C7 C 0.1725(2) 0.5910(2) 0.15611(13) 0.0275(5) Uani 1 1 d . . . H7 H 0.2410 0.5286 0.1719 0.033 Uiso 1 1 calc R . . C8 C 0.1672(2) 0.9083(2) 0.35621(15) 0.0315(5) Uani 1 1 d . . . H8A H 0.0821 0.9032 0.3884 0.038 Uiso 1 1 calc R . . H8B H 0.1465 0.9454 0.3014 0.038 Uiso 1 1 calc R . . C9 C 0.2730(2) 0.9919(2) 0.39930(15) 0.0318(5) Uani 1 1 d . . . H9A H 0.2701 0.9771 0.4591 0.038 Uiso 1 1 calc R . . H9B H 0.2605 1.0894 0.3879 0.038 Uiso 1 1 calc R . . C10 C 0.4054(2) 0.9400(2) 0.36296(14) 0.0258(5) Uani 1 1 d . . . H10A H 0.4816 0.9552 0.4014 0.031 Uiso 1 1 calc R . . H10B H 0.4258 0.9876 0.3112 0.031 Uiso 1 1 calc R . . C11 C 0.3859(2) 0.7876(2) 0.34727(12) 0.0205(4) Uani 1 1 d . . . C12 C 0.4483(2) 0.6991(2) 0.41483(12) 0.0220(4) Uani 1 1 d . . . H12 H 0.4155 0.6048 0.4053 0.026 Uiso 1 1 calc R . . C13 C 0.6029(2) 0.6941(2) 0.41420(13) 0.0264(5) Uani 1 1 d . . . H13 H 0.6329 0.6212 0.4525 0.032 Uiso 1 1 calc R . . C14 C 0.6588(2) 0.6624(3) 0.32981(13) 0.0328(5) Uani 1 1 d . . . H14A H 0.7591 0.6719 0.3305 0.039 Uiso 1 1 calc R . . H14B H 0.6370 0.5676 0.3157 0.039 Uiso 1 1 calc R . . C15 C 0.6002(2) 0.7551(2) 0.26536(13) 0.0306(5) Uani 1 1 d . . . H15A H 0.6365 0.7297 0.2111 0.037 Uiso 1 1 calc R . . H15B H 0.6278 0.8494 0.2768 0.037 Uiso 1 1 calc R . . C16 C 0.4456(2) 0.7452(2) 0.26455(12) 0.0246(5) Uani 1 1 d . . . H16A H 0.4182 0.6512 0.2522 0.030 Uiso 1 1 calc R . . H16B H 0.4088 0.8043 0.2211 0.030 Uiso 1 1 calc R . . N1 N 0.23330(17) 0.77501(17) 0.35024(11) 0.0220(4) Uani 1 1 d . . . O1 O 0.01771(15) 0.65310(18) 0.36140(9) 0.0331(4) Uani 1 1 d . . . O2 O 0.22782(15) 0.52888(15) 0.32730(9) 0.0275(4) Uani 1 1 d . . . O3 O 0.40240(16) 0.73793(17) 0.49371(9) 0.0300(4) Uani 1 1 d . . . H3A H 0.3170 0.7402 0.4942 0.045 Uiso 1 1 calc R . . O4 O 0.65252(15) 0.82044(15) 0.44426(9) 0.0310(4) Uani 1 1 d . . . H4 H 0.7380 0.8197 0.4443 0.047 Uiso 1 1 calc R . . S1 S 0.14510(5) 0.64719(5) 0.31937(3) 0.02265(14) 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 0.0191(10) 0.0278(12) 0.0253(10) -0.0028(9) -0.0041(8) -0.0024(9) C2 0.0292(12) 0.0336(13) 0.0328(12) -0.0066(10) -0.0053(10) 0.0072(10) C3 0.0371(14) 0.0304(12) 0.0369(13) -0.0018(11) -0.0120(11) 0.0064(10) C4 0.0361(13) 0.0256(11) 0.0283(11) 0.0003(9) -0.0040(10) -0.0081(10) C5 0.0656(18) 0.0393(14) 0.0307(13) 0.0042(11) -0.0061(13) -0.0061(14) C6 0.0320(12) 0.0326(12) 0.0274(11) -0.0072(9) 0.0013(11) -0.0031(10) C7 0.0255(11) 0.0270(11) 0.0301(11) -0.0035(9) -0.0039(9) 0.0031(9) C8 0.0276(12) 0.0273(11) 0.0397(12) -0.0017(10) -0.0017(10) 0.0067(10) C9 0.0324(13) 0.0244(11) 0.0384(12) -0.0039(10) 0.0046(11) 0.0000(9) C10 0.0258(11) 0.0219(11) 0.0298(11) 0.0018(9) -0.0001(9) -0.0029(9) C11 0.0167(10) 0.0244(11) 0.0203(10) -0.0007(9) -0.0010(8) -0.0027(8) C12 0.0234(11) 0.0233(10) 0.0193(10) -0.0004(9) -0.0010(8) -0.0028(9) C13 0.0226(11) 0.0299(11) 0.0268(11) -0.0005(9) -0.0082(9) -0.0010(9) C14 0.0190(11) 0.0431(14) 0.0364(12) -0.0123(11) -0.0014(10) 0.0030(10) C15 0.0261(12) 0.0397(14) 0.0258(11) -0.0065(10) 0.0050(9) -0.0059(10) C16 0.0254(11) 0.0297(12) 0.0188(10) -0.0015(9) -0.0003(8) -0.0011(9) N1 0.0162(9) 0.0236(10) 0.0260(8) -0.0033(8) -0.0008(7) 0.0013(7) O1 0.0210(8) 0.0473(10) 0.0309(8) -0.0035(8) 0.0022(6) -0.0066(8) O2 0.0264(8) 0.0243(8) 0.0317(8) 0.0016(6) -0.0040(7) -0.0026(6) O3 0.0217(8) 0.0476(10) 0.0207(7) 0.0012(7) 0.0019(6) -0.0038(7) O4 0.0189(8) 0.0416(10) 0.0326(8) -0.0061(7) -0.0055(7) -0.0035(7) S1 0.0174(3) 0.0276(3) 0.0229(2) -0.0008(2) -0.0016(2) -0.0023(2) _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 C7 1.385(3) . ? C1 C2 1.384(3) . ? C1 S1 1.774(2) . ? C2 C3 1.379(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C6 1.386(3) . ? C4 C5 1.501(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.384(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 N1 1.474(3) . ? C8 C9 1.505(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.520(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.542(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N1 1.506(3) . ? C11 C16 1.534(3) . ? C11 C12 1.539(3) . ? C12 O3 1.421(3) . ? C12 C13 1.520(3) . ? C12 H12 1.0000 . ? C13 O4 1.430(3) . ? C13 C14 1.519(3) . ? C13 H13 1.0000 . ? C14 C15 1.512(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.523(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? N1 S1 1.6149(17) . ? O1 S1 1.4298(16) . ? O2 S1 1.4316(15) . ? O3 H3A 0.8400 . ? O4 H4 0.8400 . ? 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 C1 C2 120.2(2) . . ? C7 C1 S1 120.04(17) . . ? C2 C1 S1 119.73(17) . . ? C3 C2 C1 119.7(2) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C6 C4 C3 118.1(2) . . ? C6 C4 C5 121.2(2) . . ? C3 C4 C5 120.7(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C4 121.5(2) . . ? C7 C6 H6 119.3 . . ? C4 C6 H6 119.3 . . ? C1 C7 C6 119.3(2) . . ? C1 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? N1 C8 C9 102.63(18) . . ? N1 C8 H8A 111.2 . . ? C9 C8 H8A 111.2 . . ? N1 C8 H8B 111.2 . . ? C9 C8 H8B 111.2 . . ? H8A C8 H8B 109.2 . . ? C8 C9 C10 102.83(18) . . ? C8 C9 H9A 111.2 . . ? C10 C9 H9A 111.2 . . ? C8 C9 H9B 111.2 . . ? C10 C9 H9B 111.2 . . ? H9A C9 H9B 109.1 . . ? C9 C10 C11 106.85(18) . . ? C9 C10 H10A 110.4 . . ? C11 C10 H10A 110.4 . . ? C9 C10 H10B 110.4 . . ? C11 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? N1 C11 C16 112.74(17) . . ? N1 C11 C12 109.06(16) . . ? C16 C11 C12 109.04(17) . . ? N1 C11 C10 101.48(16) . . ? C16 C11 C10 111.54(17) . . ? C12 C11 C10 112.84(17) . . ? O3 C12 C13 109.43(17) . . ? O3 C12 C11 111.86(17) . . ? C13 C12 C11 114.34(17) . . ? O3 C12 H12 106.9 . . ? C13 C12 H12 106.9 . . ? C11 C12 H12 106.9 . . ? O4 C13 C14 111.72(18) . . ? O4 C13 C12 108.04(17) . . ? C14 C13 C12 111.98(17) . . ? O4 C13 H13 108.3 . . ? C14 C13 H13 108.3 . . ? C12 C13 H13 108.3 . . ? C15 C14 C13 111.82(18) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? C14 C15 C16 110.31(19) . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C11 110.87(18) . . ? C15 C16 H16A 109.5 . . ? C11 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? C8 N1 C11 111.54(16) . . ? C8 N1 S1 119.03(14) . . ? C11 N1 S1 126.13(14) . . ? C12 O3 H3A 109.5 . . ? C13 O4 H4 109.5 . . ? O1 S1 O2 119.16(10) . . ? O1 S1 N1 106.70(9) . . ? O2 S1 N1 107.92(9) . . ? O1 S1 C1 105.77(9) . . ? O2 S1 C1 107.84(9) . . ? N1 S1 C1 109.16(10) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.322 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.048 data_10258b _database_code_depnum_ccdc_archive 'CCDC 912991' #TrackingRef 'web_deposit_cif_file_2_Chia-JungLiang_1354091839.10258b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H27 N1 O4 S1' _chemical_formula_sum 'C18 H27 N O4 S' _chemical_formula_weight 353.47 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' N N 0.0061 0.0033 '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 9.9411(4) _cell_length_b 14.1752(5) _cell_length_c 14.3185(6) _cell_angle_alpha 66.168(2) _cell_angle_beta 82.0060(10) _cell_angle_gamma 90.097(2) _cell_volume 1824.01(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 29422 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8962 _exptl_absorpt_correction_T_max 1.025 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19452 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.07 _reflns_number_total 6422 _reflns_number_gt 3724 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1692P)^2^+1.5991P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6422 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1596 _refine_ls_R_factor_gt 0.0982 _refine_ls_wR_factor_ref 0.2953 _refine_ls_wR_factor_gt 0.2531 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.002 _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 0.3810(6) -1.6146(4) 0.2725(4) 0.0388(14) Uani 1 1 d . . . C2 C 0.3800(6) -1.5758(5) 0.1676(5) 0.0483(16) Uani 1 1 d . . . H2 H 0.3890 -1.5048 0.1284 0.058 Uiso 1 1 calc R . . C3 C 0.3655(7) -1.6429(6) 0.1207(5) 0.0566(18) Uani 1 1 d . . . H3 H 0.3658 -1.6167 0.0497 0.068 Uiso 1 1 calc R . . C4 C 0.3505(6) -1.7499(5) 0.1792(6) 0.0525(17) Uani 1 1 d . . . C5 C 0.3339(9) -1.8235(6) 0.1290(7) 0.080(2) Uani 1 1 d . . . H5A H 0.3242 -1.8932 0.1807 0.121 Uiso 1 1 calc R . . H5B H 0.4127 -1.8156 0.0787 0.121 Uiso 1 1 calc R . . H5C H 0.2544 -1.8087 0.0956 0.121 Uiso 1 1 calc R . . C6 C 0.3503(6) -1.7864(5) 0.2841(5) 0.0514(17) Uani 1 1 d . . . H6 H 0.3400 -1.8573 0.3238 0.062 Uiso 1 1 calc R . . C7 C 0.3652(6) -1.7205(4) 0.3317(5) 0.0429(14) Uani 1 1 d . . . H7 H 0.3645 -1.7466 0.4027 0.051 Uiso 1 1 calc R . . C8 C 0.1434(6) -1.5437(4) 0.3886(5) 0.0453(15) Uani 1 1 d . . . H8A H 0.1440 -1.5696 0.4625 0.054 Uiso 1 1 calc R . . H8B H 0.1344 -1.6014 0.3695 0.054 Uiso 1 1 calc R . . C9 C 0.0324(6) -1.4701(5) 0.3556(5) 0.0477(16) Uani 1 1 d . . . H9A H 0.0134 -1.4612 0.2880 0.057 Uiso 1 1 calc R . . H9B H -0.0507 -1.4945 0.4049 0.057 Uiso 1 1 calc R . . C10 C 0.0913(6) -1.3712(4) 0.3529(5) 0.0421(14) Uani 1 1 d . . . H10A H 0.0778 -1.3719 0.4216 0.051 Uiso 1 1 calc R . . H10B H 0.0479 -1.3125 0.3077 0.051 Uiso 1 1 calc R . . C11 C 0.2450(5) -1.3643(4) 0.3118(4) 0.0343(13) Uani 1 1 d . . . C12 C 0.3353(6) -1.3277(4) 0.3705(4) 0.0362(13) Uani 1 1 d . . . H12 H 0.4294 -1.3401 0.3495 0.043 Uiso 1 1 calc R . . C13 C 0.3304(6) -1.2146(4) 0.3451(5) 0.0425(14) Uani 1 1 d . . . H13 H 0.3978 -1.1974 0.3805 0.051 Uiso 1 1 calc R . . C14 C 0.3732(6) -1.1512(5) 0.2297(5) 0.0498(16) Uani 1 1 d . . . H14A H 0.4682 -1.1612 0.2116 0.060 Uiso 1 1 calc R . . H14B H 0.3659 -1.0787 0.2157 0.060 Uiso 1 1 calc R . . C15 C 0.2905(6) -1.1774(4) 0.1601(4) 0.0429(15) Uani 1 1 d . . . C16 C 0.1507(7) -1.1312(5) 0.1570(6) 0.065(2) Uani 1 1 d . . . H16A H 0.1014 -1.1506 0.1138 0.097 Uiso 1 1 calc R . . H16B H 0.1628 -1.0572 0.1297 0.097 Uiso 1 1 calc R . . H16C H 0.1005 -1.1568 0.2257 0.097 Uiso 1 1 calc R . . C17 C 0.3689(8) -1.1313(6) 0.0508(5) 0.072(2) Uani 1 1 d . . . H17A H 0.4563 -1.1600 0.0504 0.108 Uiso 1 1 calc R . . H17B H 0.3812 -1.0577 0.0275 0.108 Uiso 1 1 calc R . . H17C H 0.3189 -1.1470 0.0057 0.108 Uiso 1 1 calc R . . C18 C 0.2811(6) -1.2971(4) 0.1951(4) 0.0379(13) Uani 1 1 d . . . H18A H 0.2135 -1.3139 0.1605 0.046 Uiso 1 1 calc R . . H18B H 0.3680 -1.3168 0.1708 0.046 Uiso 1 1 calc R . . C19 C 0.7093(6) -1.1234(4) 0.2803(4) 0.0373(13) Uani 1 1 d . . . C20 C 0.7001(6) -1.2282(4) 0.3384(5) 0.0410(14) Uani 1 1 d . . . H20 H 0.6700 -1.2542 0.4091 0.049 Uiso 1 1 calc R . . C21 C 0.7357(6) -1.2953(5) 0.2918(5) 0.0476(16) Uani 1 1 d . . . H21 H 0.7298 -1.3661 0.3319 0.057 Uiso 1 1 calc R . . C22 C 0.7795(6) -1.2589(5) 0.1871(5) 0.0463(15) Uani 1 1 d . . . C23 C 0.8170(9) -1.3301(6) 0.1352(6) 0.074(2) Uani 1 1 d . . . H23A H 0.8457 -1.2903 0.0627 0.111 Uiso 1 1 calc R . . H23B H 0.7394 -1.3753 0.1449 0.111 Uiso 1 1 calc R . . H23C H 0.8899 -1.3704 0.1648 0.111 Uiso 1 1 calc R . . C24 C 0.7897(7) -1.1514(5) 0.1300(5) 0.0515(16) Uani 1 1 d . . . H24 H 0.8190 -1.1250 0.0592 0.062 Uiso 1 1 calc R . . C25 C 0.7581(7) -1.0847(5) 0.1750(5) 0.0476(15) Uani 1 1 d . . . H25 H 0.7690 -1.0138 0.1358 0.057 Uiso 1 1 calc R . . C26 C 0.9050(6) -1.0456(4) 0.3881(5) 0.0468(16) Uani 1 1 d . . . H26A H 0.9228 -1.1027 0.3682 0.056 Uiso 1 1 calc R . . H26B H 0.8761 -1.0724 0.4622 0.056 Uiso 1 1 calc R . . C27 C 1.0272(6) -0.9701(5) 0.3542(5) 0.0483(16) Uani 1 1 d . . . H27A H 1.0742 -0.9620 0.2871 0.058 Uiso 1 1 calc R . . H27B H 1.0903 -0.9926 0.4038 0.058 Uiso 1 1 calc R . . C28 C 0.9673(6) -0.8699(4) 0.3492(5) 0.0426(15) Uani 1 1 d . . . H28A H 1.0277 -0.8110 0.3025 0.051 Uiso 1 1 calc R . . H28B H 0.9534 -0.8687 0.4171 0.051 Uiso 1 1 calc R . . C29 C 0.8296(5) -0.8668(4) 0.3093(4) 0.0350(13) Uani 1 1 d . . . C30 C 0.7156(6) -0.8301(4) 0.3667(4) 0.0352(13) Uani 1 1 d . . . H30 H 0.6296 -0.8439 0.3470 0.042 Uiso 1 1 calc R . . C31 C 0.7308(6) -0.7152(4) 0.3406(5) 0.0397(14) Uani 1 1 d . . . H31 H 0.6497 -0.6974 0.3760 0.048 Uiso 1 1 calc R . . C32 C 0.7324(6) -0.6563(4) 0.2250(5) 0.0463(15) Uani 1 1 d . . . H32A H 0.7447 -0.5830 0.2081 0.056 Uiso 1 1 calc R . . H32B H 0.6441 -0.6683 0.2089 0.056 Uiso 1 1 calc R . . C33 C 0.8422(6) -0.6839(4) 0.1550(4) 0.0418(14) Uani 1 1 d . . . C34 C 0.9837(7) -0.6342(5) 0.1485(6) 0.0609(19) Uani 1 1 d . . . H34A H 0.9787 -0.5608 0.1256 0.091 Uiso 1 1 calc R . . H34B H 1.0485 -0.6486 0.1005 0.091 Uiso 1 1 calc R . . H34C H 1.0117 -0.6623 0.2155 0.091 Uiso 1 1 calc R . . C35 C 0.8064(8) -0.6404(5) 0.0447(5) 0.063(2) Uani 1 1 d . . . H35A H 0.8070 -0.5664 0.0185 0.094 Uiso 1 1 calc R . . H35B H 0.7176 -0.6680 0.0459 0.094 Uiso 1 1 calc R . . H35C H 0.8723 -0.6597 0.0009 0.094 Uiso 1 1 calc R . . C36 C 0.8382(6) -0.8022(4) 0.1925(4) 0.0389(14) Uani 1 1 d . . . H36A H 0.9192 -0.8195 0.1579 0.047 Uiso 1 1 calc R . . H36B H 0.7605 -0.8236 0.1699 0.047 Uiso 1 1 calc R . . N1 N 0.2661(4) -1.4756(3) 0.3294(4) 0.0365(11) Uani 1 1 d . . . N2 N 0.8041(5) -0.9795(3) 0.3309(4) 0.0387(12) Uani 1 1 d . . . O1 O 0.4348(5) -1.5894(3) 0.4330(3) 0.0543(12) Uani 1 1 d . . . O2 O 0.5126(4) -1.4510(3) 0.2628(4) 0.0525(12) Uani 1 1 d . . . O3 O 0.3010(4) -1.3898(3) 0.4798(3) 0.0484(11) Uani 1 1 d . . . H3' H 0.2839 -1.3521 0.5102 0.073 Uiso 1 1 calc R . . O4 O 0.2018(4) -1.1870(3) 0.3812(4) 0.0565(12) Uani 1 1 d . . . H4' H 0.1492 -1.2385 0.4092 0.085 Uiso 1 1 calc R . . O5 O 0.5798(4) -0.9600(3) 0.2695(3) 0.0502(11) Uani 1 1 d . . . O6 O 0.5957(4) -1.0959(3) 0.4399(3) 0.0562(12) Uani 1 1 d . . . O7 O 0.7084(4) -0.8886(3) 0.4768(3) 0.0475(11) Uani 1 1 d . . . H7' H 0.6462 -0.8692 0.5074 0.071 Uiso 1 1 calc R . . O8 O 0.8455(4) -0.6850(3) 0.3722(3) 0.0532(11) Uani 1 1 d . . . H8' H 0.8419 -0.7169 0.4348 0.080 Uiso 1 1 calc R . . S1 S 0.40869(14) -1.52862(11) 0.33001(12) 0.0395(4) Uani 1 1 d . . . S2 S 0.66008(14) -1.03539(11) 0.33528(12) 0.0392(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 0.038(3) 0.038(3) 0.043(3) -0.019(3) -0.007(3) 0.013(2) C2 0.055(4) 0.040(4) 0.049(4) -0.016(3) -0.013(3) 0.005(3) C3 0.060(4) 0.070(5) 0.050(4) -0.033(4) -0.018(3) 0.021(4) C4 0.042(4) 0.063(5) 0.070(5) -0.043(4) -0.015(3) 0.013(3) C5 0.084(6) 0.081(6) 0.111(7) -0.073(5) -0.023(5) 0.014(4) C6 0.047(4) 0.042(4) 0.070(5) -0.027(4) -0.011(3) 0.007(3) C7 0.046(4) 0.040(4) 0.046(4) -0.020(3) -0.010(3) 0.004(3) C8 0.040(3) 0.035(3) 0.060(4) -0.020(3) -0.003(3) 0.000(3) C9 0.036(3) 0.045(4) 0.062(4) -0.023(3) -0.003(3) -0.003(3) C10 0.032(3) 0.040(3) 0.051(4) -0.018(3) -0.002(3) 0.007(2) C11 0.033(3) 0.035(3) 0.037(3) -0.017(3) -0.002(2) 0.005(2) C12 0.035(3) 0.037(3) 0.040(3) -0.019(3) -0.004(2) 0.010(2) C13 0.039(3) 0.043(4) 0.057(4) -0.032(3) -0.010(3) 0.006(3) C14 0.051(4) 0.031(3) 0.062(4) -0.013(3) -0.008(3) -0.002(3) C15 0.047(4) 0.038(4) 0.037(3) -0.009(3) -0.007(3) 0.000(3) C16 0.066(5) 0.049(4) 0.075(5) -0.015(4) -0.029(4) 0.017(3) C17 0.078(5) 0.063(5) 0.054(4) -0.004(4) -0.002(4) -0.008(4) C18 0.041(3) 0.039(3) 0.035(3) -0.016(3) -0.007(3) 0.000(3) C19 0.039(3) 0.032(3) 0.046(3) -0.018(3) -0.016(3) 0.002(2) C20 0.046(3) 0.033(3) 0.042(3) -0.013(3) -0.009(3) 0.003(3) C21 0.048(4) 0.036(3) 0.063(4) -0.022(3) -0.016(3) 0.008(3) C22 0.041(3) 0.048(4) 0.064(4) -0.037(4) -0.013(3) 0.007(3) C23 0.080(5) 0.082(6) 0.091(6) -0.065(5) -0.020(5) 0.018(4) C24 0.057(4) 0.051(4) 0.048(4) -0.021(3) -0.011(3) 0.004(3) C25 0.056(4) 0.039(4) 0.051(4) -0.019(3) -0.016(3) 0.004(3) C26 0.052(4) 0.033(3) 0.062(4) -0.020(3) -0.026(3) 0.016(3) C27 0.041(3) 0.048(4) 0.063(4) -0.025(3) -0.020(3) 0.012(3) C28 0.038(3) 0.041(3) 0.053(4) -0.021(3) -0.014(3) 0.004(3) C29 0.035(3) 0.031(3) 0.040(3) -0.016(3) -0.004(2) 0.004(2) C30 0.038(3) 0.034(3) 0.036(3) -0.016(3) -0.007(2) 0.003(2) C31 0.038(3) 0.040(3) 0.052(4) -0.031(3) -0.003(3) 0.001(3) C32 0.048(4) 0.034(3) 0.057(4) -0.019(3) -0.010(3) 0.003(3) C33 0.045(3) 0.032(3) 0.042(3) -0.009(3) -0.005(3) 0.001(3) C34 0.052(4) 0.045(4) 0.071(5) -0.015(4) 0.008(4) -0.007(3) C35 0.078(5) 0.049(4) 0.044(4) -0.001(3) -0.013(4) 0.008(4) C36 0.039(3) 0.043(4) 0.037(3) -0.019(3) -0.004(3) 0.002(3) N1 0.029(2) 0.027(3) 0.051(3) -0.016(2) 0.001(2) 0.0008(19) N2 0.041(3) 0.029(3) 0.051(3) -0.017(2) -0.022(2) 0.001(2) O1 0.065(3) 0.057(3) 0.053(3) -0.029(2) -0.027(2) 0.018(2) O2 0.032(2) 0.046(3) 0.081(3) -0.033(2) 0.008(2) -0.0002(18) O3 0.057(3) 0.055(3) 0.038(2) -0.023(2) -0.007(2) 0.013(2) O4 0.051(3) 0.056(3) 0.077(3) -0.042(3) -0.011(2) 0.016(2) O5 0.044(2) 0.039(2) 0.078(3) -0.028(2) -0.033(2) 0.0146(19) O6 0.059(3) 0.050(3) 0.057(3) -0.024(2) 0.006(2) -0.003(2) O7 0.052(3) 0.053(3) 0.037(2) -0.021(2) -0.0014(19) -0.002(2) O8 0.054(3) 0.055(3) 0.063(3) -0.036(2) -0.012(2) -0.002(2) S1 0.0346(8) 0.0385(9) 0.0522(9) -0.0252(7) -0.0076(7) 0.0076(6) S2 0.0356(8) 0.0349(8) 0.0526(9) -0.0224(7) -0.0100(7) 0.0035(6) _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 C2 1.377(8) . ? C1 C7 1.389(8) . ? C1 S1 1.764(6) . ? C2 C3 1.387(9) . ? C2 H2 0.9300 . ? C3 C4 1.400(9) . ? C3 H3 0.9300 . ? C4 C6 1.377(9) . ? C4 C5 1.508(9) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.379(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N1 1.478(7) . ? C8 C9 1.509(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.503(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.548(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N1 1.513(7) . ? C11 C12 1.531(8) . ? C11 C18 1.541(7) . ? C12 O3 1.441(6) . ? C12 C13 1.496(8) . ? C12 H12 0.9800 . ? C13 O4 1.427(7) . ? C13 C14 1.524(8) . ? C13 H13 0.9800 . ? C14 C15 1.527(9) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C17 1.521(8) . ? C15 C16 1.536(9) . ? C15 C18 1.561(8) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.373(8) . ? C19 C25 1.392(8) . ? C19 S2 1.762(6) . ? C20 C21 1.387(8) . ? C20 H20 0.9300 . ? C21 C22 1.377(9) . ? C21 H21 0.9300 . ? C22 C24 1.403(9) . ? C22 C23 1.497(9) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.358(9) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 N2 1.472(7) . ? C26 C27 1.507(8) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.520(8) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.549(8) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 N2 1.513(7) . ? C29 C30 1.522(8) . ? C29 C36 1.539(7) . ? C30 O7 1.446(6) . ? C30 C31 1.519(7) . ? C30 H30 0.9800 . ? C31 O8 1.410(7) . ? C31 C32 1.521(8) . ? C31 H31 0.9800 . ? C32 C33 1.537(8) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C36 1.540(8) . ? C33 C35 1.540(8) . ? C33 C34 1.546(9) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? N1 S1 1.605(4) . ? N2 S2 1.616(5) . ? O1 S1 1.437(4) . ? O2 S1 1.438(4) . ? O3 H3' 0.8200 . ? O4 H4' 0.8200 . ? O5 S2 1.437(4) . ? O6 S2 1.443(4) . ? O7 H7' 0.8200 . ? O8 H8' 0.8200 . ? 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 C2 C1 C7 120.4(6) . . ? C2 C1 S1 119.2(5) . . ? C7 C1 S1 120.4(4) . . ? C1 C2 C3 119.7(6) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 120.6(6) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C6 C4 C3 118.4(6) . . ? C6 C4 C5 120.6(7) . . ? C3 C4 C5 121.0(7) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C4 121.6(6) . . ? C7 C6 H6 119.2 . . ? C4 C6 H6 119.2 . . ? C6 C7 C1 119.3(6) . . ? C6 C7 H7 120.3 . . ? C1 C7 H7 120.3 . . ? N1 C8 C9 101.1(4) . . ? N1 C8 H8A 111.5 . . ? C9 C8 H8A 111.5 . . ? N1 C8 H8B 111.5 . . ? C9 C8 H8B 111.5 . . ? H8A C8 H8B 109.4 . . ? C10 C9 C8 103.2(5) . . ? C10 C9 H9A 111.1 . . ? C8 C9 H9A 111.1 . . ? C10 C9 H9B 111.1 . . ? C8 C9 H9B 111.1 . . ? H9A C9 H9B 109.1 . . ? C9 C10 C11 106.4(5) . . ? C9 C10 H10A 110.4 . . ? C11 C10 H10A 110.4 . . ? C9 C10 H10B 110.4 . . ? C11 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? N1 C11 C12 111.3(4) . . ? N1 C11 C18 108.1(4) . . ? C12 C11 C18 109.4(4) . . ? N1 C11 C10 101.0(4) . . ? C12 C11 C10 113.4(5) . . ? C18 C11 C10 113.4(5) . . ? O3 C12 C13 112.2(5) . . ? O3 C12 C11 109.6(4) . . ? C13 C12 C11 113.1(5) . . ? O3 C12 H12 107.2 . . ? C13 C12 H12 107.2 . . ? C11 C12 H12 107.2 . . ? O4 C13 C12 113.3(5) . . ? O4 C13 C14 111.4(5) . . ? C12 C13 C14 110.7(5) . . ? O4 C13 H13 107.0 . . ? C12 C13 H13 107.0 . . ? C14 C13 H13 107.0 . . ? C13 C14 C15 114.9(5) . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14B 108.5 . . ? C15 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C17 C15 C14 108.0(5) . . ? C17 C15 C16 107.8(5) . . ? C14 C15 C16 112.1(6) . . ? C17 C15 C18 106.8(5) . . ? C14 C15 C18 108.8(5) . . ? C16 C15 C18 113.1(5) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C11 C18 C15 117.3(5) . . ? C11 C18 H18A 108.0 . . ? C15 C18 H18A 108.0 . . ? C11 C18 H18B 108.0 . . ? C15 C18 H18B 108.0 . . ? H18A C18 H18B 107.2 . . ? C20 C19 C25 119.7(6) . . ? C20 C19 S2 121.8(5) . . ? C25 C19 S2 118.5(4) . . ? C19 C20 C21 120.2(6) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 121.1(6) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C24 117.5(6) . . ? C21 C22 C23 121.9(6) . . ? C24 C22 C23 120.7(6) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C22 122.1(6) . . ? C25 C24 H24 119.0 . . ? C22 C24 H24 119.0 . . ? C24 C25 C19 119.5(6) . . ? C24 C25 H25 120.3 . . ? C19 C25 H25 120.3 . . ? N2 C26 C27 101.1(4) . . ? N2 C26 H26A 111.6 . . ? C27 C26 H26A 111.6 . . ? N2 C26 H26B 111.6 . . ? C27 C26 H26B 111.6 . . ? H26A C26 H26B 109.4 . . ? C26 C27 C28 103.9(5) . . ? C26 C27 H27A 111.0 . . ? C28 C27 H27A 111.0 . . ? C26 C27 H27B 111.0 . . ? C28 C27 H27B 111.0 . . ? H27A C27 H27B 109.0 . . ? C27 C28 C29 106.1(5) . . ? C27 C28 H28A 110.5 . . ? C29 C28 H28A 110.5 . . ? C27 C28 H28B 110.5 . . ? C29 C28 H28B 110.5 . . ? H28A C28 H28B 108.7 . . ? N2 C29 C30 111.3(4) . . ? N2 C29 C36 108.6(4) . . ? C30 C29 C36 109.1(4) . . ? N2 C29 C28 100.6(4) . . ? C30 C29 C28 113.3(5) . . ? C36 C29 C28 113.5(5) . . ? O7 C30 C31 109.9(4) . . ? O7 C30 C29 109.7(4) . . ? C31 C30 C29 113.2(5) . . ? O7 C30 H30 107.9 . . ? C31 C30 H30 107.9 . . ? C29 C30 H30 107.9 . . ? O8 C31 C32 111.0(5) . . ? O8 C31 C30 114.3(5) . . ? C32 C31 C30 108.4(5) . . ? O8 C31 H31 107.6 . . ? C32 C31 H31 107.6 . . ? C30 C31 H31 107.6 . . ? C31 C32 C33 115.8(5) . . ? C31 C32 H32A 108.3 . . ? C33 C32 H32A 108.3 . . ? C31 C32 H32B 108.3 . . ? C33 C32 H32B 108.3 . . ? H32A C32 H32B 107.4 . . ? C32 C33 C36 108.7(5) . . ? C32 C33 C35 108.8(5) . . ? C36 C33 C35 106.7(5) . . ? C32 C33 C34 111.5(5) . . ? C36 C33 C34 113.8(5) . . ? C35 C33 C34 107.0(5) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 C29 117.4(5) . . ? C33 C36 H36A 108.0 . . ? C29 C36 H36A 108.0 . . ? C33 C36 H36B 108.0 . . ? C29 C36 H36B 108.0 . . ? H36A C36 H36B 107.2 . . ? C8 N1 C11 111.5(4) . . ? C8 N1 S1 117.4(3) . . ? C11 N1 S1 126.9(3) . . ? C26 N2 C29 112.9(4) . . ? C26 N2 S2 117.1(4) . . ? C29 N2 S2 126.1(4) . . ? C12 O3 H3' 109.5 . . ? C13 O4 H4' 109.5 . . ? C30 O7 H7' 109.5 . . ? C31 O8 H8' 109.5 . . ? O1 S1 O2 116.8(3) . . ? O1 S1 N1 112.2(3) . . ? O2 S1 N1 108.6(2) . . ? O1 S1 C1 107.5(3) . . ? O2 S1 C1 108.5(3) . . ? N1 S1 C1 102.3(3) . . ? O5 S2 O6 116.5(3) . . ? O5 S2 N2 108.8(2) . . ? O6 S2 N2 112.3(3) . . ? O5 S2 C19 109.1(3) . . ? O6 S2 C19 106.7(3) . . ? N2 S2 C19 102.5(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.359 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.112