# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 _publ_contact_author_name 'Dr Alan C. Spivey' _publ_contact_author_address ; Chemistry Imperial College London South Kensington campus London SW7 2AZ UNITED KINGDOM ; _publ_contact_author_email A.C.SPIVEY@IMPERIAL.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; The Synthesis of Water Soluble Decalin-based Thiols and S-Nitrosothiols - Model Systems for Studying the Reactions of Nitric Oxide with Protein Thiols ; loop_ _publ_author_name _publ_author_address 'Frampton, Christopher S.' ;Pharmorphix Ltd., 250 cambridge Science Park Milton Road Cambridge CB4 0WE UK ; 'Spivey, Alan C.' ;Department of Chemistry Imperial College South Kensington campus London SW7 2AZ UK ; 'Chigboh, Kordi I.' ;Department of Chemistry Imperial College South Kensington campus London SW7 2AZ UK ; 'Colley, Jacqueline' ;Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF UK ; 'Sprigens, Lindsey' ;Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF UK ; 'Hancock, Susan M.' ;Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF UK ; 'Cameron, D. Stuart' ;Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF UK ; 'Adams, Harry' ;Department of Chemistry University of Sheffield Brook Hill Sheffield S3 7HF UK ; 'Gemma Veitch' ; Department of Chemistry Imperial College South Kensington campus London SW7 2AZ UK ; data_s95 _database_code_depnum_ccdc_archive 'CCDC 266148' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H27 N O6 S' _chemical_formula_weight 361.45 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/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 15.095(1) _cell_length_b 10.338(6) _cell_length_c 11.718(5) _cell_angle_alpha 90.0000 _cell_angle_beta 97.582(4) _cell_angle_gamma 90.0000 _cell_volume 1812.7(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(1) _cell_measurement_reflns_used 4268 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator ; graphite graded mirror ; _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method CCD _diffrn_reflns_number 3744 _diffrn_reflns_av_R_equivalents 0.1151 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3744 _reflns_number_gt 2778 _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 (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXTL V5.10 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL V5.10 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.10 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL V5.10 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1380P)^2^+7.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3699 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1230 _refine_ls_R_factor_gt 0.0943 _refine_ls_wR_factor_ref 0.2950 _refine_ls_wR_factor_gt 0.2759 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 S1 S 0.02620(10) 0.03366(15) 0.18283(13) 0.0399(4) Uani 1 1 d . . . O1 O -0.1138(3) -0.0190(5) 0.2637(5) 0.0672(15) Uani 1 1 d . . . O2 O 0.2897(2) -0.0198(3) 0.2272(3) 0.0295(8) Uani 1 1 d . . . O3 O 0.6061(3) -0.0343(4) 0.2929(4) 0.0422(10) Uani 1 1 d . . . O4 O 0.4500(3) -0.0159(4) 0.3794(3) 0.0337(9) Uani 1 1 d . . . O5 O 0.4635(4) -0.3079(4) 0.5412(4) 0.0568(13) Uani 1 1 d . . . O6 O 0.5646(3) -0.2119(4) 0.4510(4) 0.0417(10) Uani 1 1 d . . . H6C H 0.574(5) -0.150(8) 0.427(7) 0.06(3) Uiso 1 1 d . . . N1 N -0.0372(4) -0.0460(6) 0.2763(5) 0.0542(15) Uani 1 1 d . . . C1 C 0.1559(4) -0.0030(5) 0.3706(4) 0.0352(12) Uani 1 1 d . . . H1A H 0.1082 -0.0423 0.4097 0.042 Uiso 1 1 calc R . . H1B H 0.2132 -0.0439 0.4022 0.042 Uiso 1 1 calc R . . C2 C 0.1608(5) 0.1412(6) 0.3975(5) 0.0449(15) Uani 1 1 d . . . H2A H 0.1008 0.1799 0.3777 0.054 Uiso 1 1 calc R . . H2B H 0.1791 0.1534 0.4811 0.054 Uiso 1 1 calc R . . C3 C 0.2263(4) 0.2105(6) 0.3316(5) 0.0434(14) Uani 1 1 d . . . H3A H 0.2878 0.1821 0.3605 0.052 Uiso 1 1 calc R . . H3B H 0.2225 0.3048 0.3449 0.052 Uiso 1 1 calc R . . C4 C 0.2067(4) 0.1829(5) 0.2027(5) 0.0374(13) Uani 1 1 d . . . H4A H 0.2525 0.2259 0.1626 0.045 Uiso 1 1 calc R . . H4B H 0.1478 0.2198 0.1724 0.045 Uiso 1 1 calc R . . C5 C 0.1904(4) 0.0080(5) 0.0474(4) 0.0355(12) Uani 1 1 d . . . H5A H 0.1317 0.0435 0.0143 0.043 Uiso 1 1 calc R . . H5B H 0.2371 0.0508 0.0088 0.043 Uiso 1 1 calc R . . C6 C 0.1921(4) -0.1365(6) 0.0247(5) 0.0402(13) Uani 1 1 d . . . H6A H 0.2530 -0.1701 0.0493 0.048 Uiso 1 1 calc R . . H6B H 0.1773 -0.1524 -0.0589 0.048 Uiso 1 1 calc R . . C7 C 0.1260(4) -0.2085(6) 0.0888(5) 0.0415(14) Uani 1 1 d . . . H7A H 0.1335 -0.3027 0.0782 0.050 Uiso 1 1 calc R . . H7B H 0.0644 -0.1853 0.0550 0.050 Uiso 1 1 calc R . . C8 C 0.1377(4) -0.1782(5) 0.2170(5) 0.0360(12) Uani 1 1 d . . . H8A H 0.1950 -0.2153 0.2534 0.043 Uiso 1 1 calc R . . H8B H 0.0889 -0.2200 0.2523 0.043 Uiso 1 1 calc R . . C9 C 0.1371(3) -0.0325(5) 0.2416(4) 0.0299(11) Uani 1 1 d . . . C10 C 0.2067(3) 0.0379(5) 0.1771(4) 0.0297(11) Uani 1 1 d . . . C11 C 0.3685(4) 0.0342(5) 0.1925(5) 0.0351(12) Uani 1 1 d . . . H11A H 0.3704 0.1283 0.2080 0.042 Uiso 1 1 calc R . . H11B H 0.3686 0.0210 0.1089 0.042 Uiso 1 1 calc R . . C12 C 0.4485(4) -0.0297(5) 0.2577(4) 0.0318(11) Uani 1 1 d . . . H12A H 0.4477 -0.1238 0.2379 0.038 Uiso 1 1 calc R . . C13 C 0.5332(4) 0.0292(5) 0.2287(5) 0.0337(12) Uani 1 1 d . . . H13A H 0.5367 0.0196 0.1453 0.040 Uiso 1 1 calc R . . H13B H 0.5348 0.1226 0.2475 0.040 Uiso 1 1 calc R . . C14 C 0.6889(4) 0.0278(7) 0.2832(6) 0.0490(16) Uani 1 1 d . . . H14A H 0.7372 -0.0176 0.3312 0.074 Uiso 1 1 calc R . . H14B H 0.6864 0.1177 0.3089 0.074 Uiso 1 1 calc R . . H14C H 0.7001 0.0259 0.2027 0.074 Uiso 1 1 calc R . . C15 C 0.4152(4) -0.1216(6) 0.4358(5) 0.0371(13) Uani 1 1 d . . . H15A H 0.3681 -0.1638 0.3816 0.045 Uiso 1 1 calc R . . H15B H 0.3867 -0.0882 0.5013 0.045 Uiso 1 1 calc R . . C16 C 0.4831(4) -0.2213(5) 0.4801(5) 0.0386(13) 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 S1 0.0358(8) 0.0436(8) 0.0394(8) 0.0026(6) 0.0023(6) 0.0040(6) O1 0.044(3) 0.066(3) 0.092(4) -0.004(3) 0.012(3) 0.000(2) O2 0.0309(18) 0.0293(18) 0.0277(17) 0.0055(14) 0.0011(14) 0.0007(15) O3 0.036(2) 0.040(2) 0.052(2) 0.0075(19) 0.0102(18) -0.0028(17) O4 0.039(2) 0.035(2) 0.0269(18) -0.0006(15) 0.0046(15) -0.0026(16) O5 0.082(3) 0.042(2) 0.050(3) 0.016(2) 0.022(2) 0.007(2) O6 0.053(3) 0.033(2) 0.037(2) -0.0010(19) 0.0015(19) 0.007(2) N1 0.037(3) 0.055(4) 0.071(4) -0.014(3) 0.007(3) -0.005(2) C1 0.041(3) 0.042(3) 0.023(2) 0.001(2) 0.005(2) 0.003(2) C2 0.060(4) 0.047(4) 0.027(3) -0.008(2) 0.005(3) 0.006(3) C3 0.057(4) 0.033(3) 0.038(3) -0.005(2) -0.002(3) 0.000(3) C4 0.050(3) 0.024(3) 0.037(3) 0.003(2) 0.003(2) 0.003(2) C5 0.041(3) 0.039(3) 0.024(3) -0.001(2) -0.002(2) 0.003(2) C6 0.044(3) 0.046(3) 0.029(3) -0.006(2) 0.002(2) 0.004(3) C7 0.047(3) 0.035(3) 0.042(3) -0.012(2) 0.004(3) -0.002(3) C8 0.040(3) 0.033(3) 0.036(3) 0.003(2) 0.008(2) -0.003(2) C9 0.029(3) 0.032(3) 0.028(3) -0.001(2) 0.001(2) 0.002(2) C10 0.033(3) 0.028(3) 0.027(2) 0.001(2) 0.000(2) 0.002(2) C11 0.040(3) 0.033(3) 0.033(3) 0.005(2) 0.005(2) -0.002(2) C12 0.039(3) 0.030(3) 0.027(3) -0.004(2) 0.004(2) -0.004(2) C13 0.037(3) 0.030(3) 0.035(3) 0.002(2) 0.005(2) -0.002(2) C14 0.032(3) 0.055(4) 0.062(4) 0.004(3) 0.012(3) -0.004(3) C15 0.045(3) 0.042(3) 0.026(3) 0.006(2) 0.009(2) -0.007(3) C16 0.051(4) 0.036(3) 0.029(3) -0.005(2) 0.006(2) -0.001(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 S1 N1 1.752(6) . ? S1 C9 1.854(5) . ? O1 N1 1.179(7) . ? O2 C11 1.420(7) . ? O2 C10 1.441(6) . ? O3 C13 1.410(7) . ? O3 C14 1.422(7) . ? O4 C15 1.414(6) . ? O4 C12 1.430(6) . ? O5 C16 1.207(7) . ? O6 C16 1.323(8) . ? O6 H6C 0.72(8) . ? C1 C2 1.524(8) . ? C1 C9 1.532(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.512(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.528(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C10 1.529(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.518(8) . ? C5 C10 1.539(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.520(9) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.522(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.534(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.554(7) . ? C11 C12 1.495(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.496(7) . ? C12 H12A 1.0000 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.497(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? 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 N1 S1 C9 97.8(3) . . ? C11 O2 C10 115.9(4) . . ? C13 O3 C14 112.3(4) . . ? C15 O4 C12 115.6(4) . . ? C16 O6 H6C 114(7) . . ? O1 N1 S1 114.7(5) . . ? C2 C1 C9 113.3(5) . . ? C2 C1 H1A 108.9 . . ? C9 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? C9 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 112.1(5) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 111.2(5) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C10 111.8(4) . . ? C3 C4 H4A 109.2 . . ? C10 C4 H4A 109.2 . . ? C3 C4 H4B 109.2 . . ? C10 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C10 111.5(4) . . ? C6 C5 H5A 109.3 . . ? C10 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C10 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C7 111.6(5) . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 112.8(5) . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C9 112.7(5) . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C1 C9 C8 112.1(4) . . ? C1 C9 C10 109.7(4) . . ? C8 C9 C10 110.3(4) . . ? C1 C9 S1 109.5(4) . . ? C8 C9 S1 108.7(4) . . ? C10 C9 S1 106.4(3) . . ? O2 C10 C4 110.4(4) . . ? O2 C10 C5 109.6(4) . . ? C4 C10 C5 112.7(4) . . ? O2 C10 C9 102.5(4) . . ? C4 C10 C9 110.3(4) . . ? C5 C10 C9 110.9(4) . . ? O2 C11 C12 109.3(4) . . ? O2 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? O2 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? O4 C12 C11 111.8(4) . . ? O4 C12 C13 106.6(4) . . ? C11 C12 C13 111.2(4) . . ? O4 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? O3 C13 C12 108.7(4) . . ? O3 C13 H13A 110.0 . . ? C12 C13 H13A 110.0 . . ? O3 C13 H13B 110.0 . . ? C12 C13 H13B 110.0 . . ? H13A C13 H13B 108.3 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 C16 114.5(5) . . ? O4 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? O4 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? O5 C16 O6 121.1(6) . . ? O5 C16 C15 120.4(6) . . ? O6 C16 C15 118.5(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 S1 N1 O1 176.9(5) . . . . ? C9 C1 C2 C3 -53.2(7) . . . . ? C1 C2 C3 C4 52.9(7) . . . . ? C2 C3 C4 C10 -56.1(7) . . . . ? C10 C5 C6 C7 55.1(6) . . . . ? C5 C6 C7 C8 -53.0(7) . . . . ? C6 C7 C8 C9 52.6(7) . . . . ? C2 C1 C9 C8 176.8(5) . . . . ? C2 C1 C9 C10 53.9(6) . . . . ? C2 C1 C9 S1 -62.5(6) . . . . ? C7 C8 C9 C1 -175.7(5) . . . . ? C7 C8 C9 C10 -53.1(6) . . . . ? C7 C8 C9 S1 63.1(5) . . . . ? N1 S1 C9 C1 -55.9(4) . . . . ? N1 S1 C9 C8 66.8(4) . . . . ? N1 S1 C9 C10 -174.4(3) . . . . ? C11 O2 C10 C4 -56.9(6) . . . . ? C11 O2 C10 C5 67.9(5) . . . . ? C11 O2 C10 C9 -174.4(4) . . . . ? C3 C4 C10 O2 -55.0(6) . . . . ? C3 C4 C10 C5 -178.0(5) . . . . ? C3 C4 C10 C9 57.5(6) . . . . ? C6 C5 C10 O2 55.8(6) . . . . ? C6 C5 C10 C4 179.2(5) . . . . ? C6 C5 C10 C9 -56.6(6) . . . . ? C1 C9 C10 O2 62.1(5) . . . . ? C8 C9 C10 O2 -61.9(5) . . . . ? S1 C9 C10 O2 -179.5(3) . . . . ? C1 C9 C10 C4 -55.4(6) . . . . ? C8 C9 C10 C4 -179.4(4) . . . . ? S1 C9 C10 C4 62.9(5) . . . . ? C1 C9 C10 C5 179.0(4) . . . . ? C8 C9 C10 C5 55.0(6) . . . . ? S1 C9 C10 C5 -62.7(5) . . . . ? C10 O2 C11 C12 176.1(4) . . . . ? C15 O4 C12 C11 96.6(5) . . . . ? C15 O4 C12 C13 -141.8(5) . . . . ? O2 C11 C12 O4 -58.0(6) . . . . ? O2 C11 C12 C13 -176.9(4) . . . . ? C14 O3 C13 C12 -171.5(5) . . . . ? O4 C12 C13 O3 57.7(5) . . . . ? C11 C12 C13 O3 179.7(4) . . . . ? C12 O4 C15 C16 91.2(6) . . . . ? O4 C15 C16 O5 171.3(5) . . . . ? O4 C15 C16 O6 -8.4(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6C O3 0.72(8) 2.08(8) 2.739(6) 151(8) . O6 H6C O4 0.72(8) 2.34(8) 2.725(6) 115(8) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.817 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.083 data_csf94s _database_code_depnum_ccdc_archive 'CCDC 266149' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 O5 S' _chemical_formula_weight 302.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8076(9) _cell_length_b 9.3008(12) _cell_length_c 12.2010(18) _cell_angle_alpha 96.400(8) _cell_angle_beta 105.284(9) _cell_angle_gamma 92.286(9) _cell_volume 738.62(17) _cell_formula_units_Z 2 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 4343 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 26.37 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS 1K CCD area detector' _diffrn_measurement_method 'narrow frame \w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_reflns_number 6317 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2987 _reflns_number_gt 2426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.060 (Bruker AXS, 1999)' _computing_cell_refinement 'SMART V5.060/SAINT V6.02a (Bruker AXS, 1999)' _computing_data_reduction 'SAINT V6.02a (Bruker AXS, 1997)' _computing_structure_solution 'SHELXTL V5.10 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL V5.10 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.10 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL V5.10 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2987 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 S1 S 0.33160(6) 0.83743(4) 0.26431(4) 0.02268(14) Uani 1 1 d . . . O1 O -0.19803(16) 1.21422(12) 0.24921(9) 0.0200(3) Uani 1 1 d . . . O2 O 0.38069(19) 1.24089(13) 0.17006(10) 0.0264(3) Uani 1 1 d . . . H2C H 0.508(4) 1.226(2) 0.2055(19) 0.044(6) Uiso 1 1 d . . . O3 O 0.36431(16) 1.00833(12) 0.29487(9) 0.0226(3) Uani 1 1 d . . . O4 O 0.12262(18) 0.79255(13) 0.25165(11) 0.0303(3) Uani 1 1 d . . . O5 O 0.4864(2) 0.78265(14) 0.35029(11) 0.0347(3) Uani 1 1 d . . . C1 C 0.1895(2) 1.09970(17) 0.27155(14) 0.0197(3) Uani 1 1 d . . . H1A H 0.0842 1.0581 0.1999 0.024 Uiso 1 1 calc R . . C2 C 0.0991(2) 1.11222(17) 0.37333(14) 0.0214(4) Uani 1 1 d . . . H2A H 0.0340 1.0168 0.3780 0.026 Uiso 1 1 calc R . . H2B H 0.2100 1.1392 0.4447 0.026 Uiso 1 1 calc R . . C3 C -0.0573(2) 1.22432(17) 0.36397(13) 0.0187(3) Uani 1 1 d . . . C4 C -0.1588(3) 1.24122(18) 0.46010(14) 0.0232(4) Uani 1 1 d . . . H4A H -0.2598 1.1578 0.4496 0.028 Uiso 1 1 calc R . . H4B H -0.0543 1.2381 0.5334 0.028 Uiso 1 1 calc R . . C5 C -0.2647(2) 1.37872(18) 0.46808(15) 0.0253(4) Uani 1 1 d . . . H5A H -0.3381 1.3920 0.5243 0.030 Uiso 1 1 calc R . . C6 C -0.2636(2) 1.48273(18) 0.40289(15) 0.0257(4) Uani 1 1 d . . . H6A H -0.3370 1.5651 0.4151 0.031 Uiso 1 1 calc R . . C7 C -0.1543(2) 1.47976(17) 0.31073(14) 0.0240(4) Uani 1 1 d . . . H7A H -0.0496 1.5623 0.3306 0.029 Uiso 1 1 calc R . . H7B H -0.2536 1.4940 0.2379 0.029 Uiso 1 1 calc R . . C8 C -0.0521(2) 1.34181(17) 0.29203(13) 0.0194(3) Uani 1 1 d . . . C9 C 0.1106(2) 1.35139(17) 0.22850(14) 0.0225(4) Uani 1 1 d . . . H9A H 0.1744 1.4517 0.2449 0.027 Uiso 1 1 calc R . . H9B H 0.0438 1.3325 0.1452 0.027 Uiso 1 1 calc R . . C10 C 0.2780(2) 1.24732(18) 0.25809(14) 0.0215(3) Uani 1 1 d . . . H10A H 0.3773 1.2880 0.3323 0.026 Uiso 1 1 calc R . . C11 C 0.3890(3) 0.80118(18) 0.12760(14) 0.0239(4) Uani 1 1 d . . . C12 C 0.2502(3) 0.8861(2) 0.04137(15) 0.0321(4) Uani 1 1 d . . . H12A H 0.2700 0.8595 -0.0348 0.048 Uiso 1 1 calc R . . H12B H 0.2844 0.9903 0.0647 0.048 Uiso 1 1 calc R . . H12C H 0.1074 0.8628 0.0391 0.048 Uiso 1 1 calc R . . C13 C 0.3424(3) 0.63728(19) 0.09066(16) 0.0310(4) Uani 1 1 d . . . H13A H 0.3782 0.6106 0.0187 0.046 Uiso 1 1 calc R . . H13B H 0.1966 0.6124 0.0795 0.046 Uiso 1 1 calc R . . H13C H 0.4226 0.5843 0.1502 0.046 Uiso 1 1 calc R . . C14 C 0.6145(3) 0.8443(2) 0.14388(17) 0.0337(4) Uani 1 1 d . . . H14A H 0.6478 0.8246 0.0705 0.051 Uiso 1 1 calc R . . H14B H 0.6982 0.7881 0.1997 0.051 Uiso 1 1 calc R . . H14C H 0.6424 0.9480 0.1719 0.051 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 S1 0.0264(2) 0.0212(2) 0.0251(2) 0.00855(16) 0.01194(17) 0.00728(16) O1 0.0174(5) 0.0205(6) 0.0214(6) 0.0021(5) 0.0047(5) -0.0011(4) O2 0.0206(6) 0.0335(7) 0.0296(7) 0.0098(5) 0.0119(5) 0.0034(5) O3 0.0200(6) 0.0220(6) 0.0268(6) 0.0040(5) 0.0067(5) 0.0062(5) O4 0.0326(7) 0.0257(6) 0.0387(7) 0.0071(5) 0.0191(6) 0.0024(5) O5 0.0429(8) 0.0347(7) 0.0308(7) 0.0144(6) 0.0111(6) 0.0176(6) C1 0.0155(7) 0.0200(8) 0.0244(8) 0.0046(6) 0.0053(6) 0.0058(6) C2 0.0238(8) 0.0199(8) 0.0228(8) 0.0071(7) 0.0080(7) 0.0029(6) C3 0.0171(7) 0.0201(8) 0.0184(8) 0.0022(6) 0.0039(6) -0.0001(6) C4 0.0252(8) 0.0244(9) 0.0222(8) 0.0039(7) 0.0095(7) 0.0023(7) C5 0.0203(8) 0.0293(9) 0.0267(9) -0.0003(7) 0.0083(7) 0.0033(7) C6 0.0188(8) 0.0230(8) 0.0342(10) -0.0010(7) 0.0066(7) 0.0058(6) C7 0.0233(8) 0.0205(8) 0.0284(9) 0.0057(7) 0.0061(7) 0.0031(7) C8 0.0165(8) 0.0194(8) 0.0206(8) 0.0016(6) 0.0030(6) -0.0018(6) C9 0.0210(8) 0.0211(8) 0.0271(9) 0.0075(7) 0.0079(7) 0.0008(6) C10 0.0182(8) 0.0258(9) 0.0218(8) 0.0054(7) 0.0068(6) 0.0006(6) C11 0.0298(9) 0.0220(8) 0.0244(9) 0.0055(7) 0.0140(7) 0.0038(7) C12 0.0471(11) 0.0290(10) 0.0221(9) 0.0066(7) 0.0106(8) 0.0071(8) C13 0.0373(10) 0.0232(9) 0.0355(10) 0.0035(8) 0.0151(8) 0.0044(7) C14 0.0338(10) 0.0316(10) 0.0417(11) 0.0055(8) 0.0205(9) 0.0005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O4 1.4299(13) . ? S1 O5 1.4318(13) . ? S1 O3 1.5846(12) . ? S1 C11 1.8103(17) . ? O1 C3 1.4639(18) . ? O1 C8 1.4705(18) . ? O2 C10 1.4250(18) . ? O2 H2C 0.89(2) . ? O3 C1 1.4749(18) . ? C1 C2 1.520(2) . ? C1 C10 1.520(2) . ? C1 H1A 1.0000 . ? C2 C3 1.512(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.481(2) . ? C3 C4 1.508(2) . ? C4 C5 1.499(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.320(2) . ? C5 H5A 0.9500 . ? C6 C7 1.502(2) . ? C6 H6A 0.9500 . ? C7 C8 1.507(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.515(2) . ? C9 C10 1.522(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 1.0000 . ? C11 C14 1.527(2) . ? C11 C12 1.531(2) . ? C11 C13 1.536(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 S1 O5 118.73(8) . . ? O4 S1 O3 109.34(7) . . ? O5 S1 O3 104.71(7) . . ? O4 S1 C11 109.47(8) . . ? O5 S1 C11 109.00(8) . . ? O3 S1 C11 104.61(7) . . ? C3 O1 C8 60.61(10) . . ? C10 O2 H2C 104.2(14) . . ? C1 O3 S1 120.79(10) . . ? O3 C1 C2 109.10(12) . . ? O3 C1 C10 105.36(12) . . ? C2 C1 C10 110.14(13) . . ? O3 C1 H1A 110.7 . . ? C2 C1 H1A 110.7 . . ? C10 C1 H1A 110.7 . . ? C3 C2 C1 111.78(13) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? O1 C3 C8 59.91(9) . . ? O1 C3 C4 114.46(12) . . ? C8 C3 C4 121.03(13) . . ? O1 C3 C2 112.80(12) . . ? C8 C3 C2 119.94(13) . . ? C4 C3 C2 115.34(13) . . ? C5 C4 C3 114.15(14) . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 124.95(15) . . ? C6 C5 H5A 117.5 . . ? C4 C5 H5A 117.5 . . ? C5 C6 C7 124.45(15) . . ? C5 C6 H6A 117.8 . . ? C7 C6 H6A 117.8 . . ? C6 C7 C8 114.49(14) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? O1 C8 C3 59.48(9) . . ? O1 C8 C7 112.94(13) . . ? C3 C8 C7 120.72(14) . . ? O1 C8 C9 113.62(13) . . ? C3 C8 C9 120.39(13) . . ? C7 C8 C9 115.62(13) . . ? C8 C9 C10 115.03(13) . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? O2 C10 C1 112.89(13) . . ? O2 C10 C9 107.15(12) . . ? C1 C10 C9 110.79(12) . . ? O2 C10 H10A 108.6 . . ? C1 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C14 C11 C12 111.88(14) . . ? C14 C11 C13 110.91(14) . . ? C12 C11 C13 110.33(15) . . ? C14 C11 S1 108.66(12) . . ? C12 C11 S1 108.83(11) . . ? C13 C11 S1 106.03(11) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 S1 O3 C1 -19.19(13) . . . . ? O5 S1 O3 C1 -147.42(11) . . . . ? C11 S1 O3 C1 97.98(12) . . . . ? S1 O3 C1 C2 87.31(14) . . . . ? S1 O3 C1 C10 -154.47(10) . . . . ? O3 C1 C2 C3 170.37(12) . . . . ? C10 C1 C2 C3 55.19(17) . . . . ? C8 O1 C3 C4 113.01(15) . . . . ? C8 O1 C3 C2 -112.47(14) . . . . ? C1 C2 C3 O1 44.43(17) . . . . ? C1 C2 C3 C8 -22.9(2) . . . . ? C1 C2 C3 C4 178.53(13) . . . . ? O1 C3 C4 C5 -63.58(18) . . . . ? C8 C3 C4 C5 4.8(2) . . . . ? C2 C3 C4 C5 163.07(14) . . . . ? C3 C4 C5 C6 -3.7(2) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C5 C6 C7 C8 3.4(2) . . . . ? C3 O1 C8 C7 -113.23(15) . . . . ? C3 O1 C8 C9 112.53(15) . . . . ? C4 C3 C8 O1 -102.11(15) . . . . ? C2 C3 C8 O1 100.55(15) . . . . ? O1 C3 C8 C7 100.13(15) . . . . ? C4 C3 C8 C7 -2.0(2) . . . . ? C2 C3 C8 C7 -159.32(14) . . . . ? O1 C3 C8 C9 -101.15(16) . . . . ? C4 C3 C8 C9 156.74(15) . . . . ? C2 C3 C8 C9 -0.6(2) . . . . ? C6 C7 C8 O1 64.94(17) . . . . ? C6 C7 C8 C3 -2.1(2) . . . . ? C6 C7 C8 C9 -161.78(14) . . . . ? O1 C8 C9 C10 -75.49(17) . . . . ? C3 C8 C9 C10 -8.2(2) . . . . ? C7 C8 C9 C10 151.55(14) . . . . ? O3 C1 C10 O2 57.44(16) . . . . ? C2 C1 C10 O2 174.97(13) . . . . ? O3 C1 C10 C9 177.62(12) . . . . ? C2 C1 C10 C9 -64.85(17) . . . . ? C8 C9 C10 O2 163.70(13) . . . . ? C8 C9 C10 C1 40.2(2) . . . . ? O4 S1 C11 C14 -177.82(11) . . . . ? O5 S1 C11 C14 -46.45(14) . . . . ? O3 S1 C11 C14 65.10(13) . . . . ? O4 S1 C11 C12 60.12(13) . . . . ? O5 S1 C11 C12 -168.51(12) . . . . ? O3 S1 C11 C12 -56.96(13) . . . . ? O4 S1 C11 C13 -58.55(13) . . . . ? O5 S1 C11 C13 72.82(13) . . . . ? O3 S1 C11 C13 -175.63(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2C O1 0.89(2) 1.94(2) 2.8052(17) 165(2) 1_655 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.281 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.048 data_oas21m _database_code_depnum_ccdc_archive 'CCDC 266150' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 N O4 S' _chemical_formula_weight 272.33 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.927(8) _cell_length_b 8.372(6) _cell_length_c 14.620(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.444(14) _cell_angle_gamma 90.00 _cell_volume 1329.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 955 _cell_measurement_theta_min 5.616 _cell_measurement_theta_max 55.759 _exptl_crystal_description PLATE _exptl_crystal_colour Green _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 150k _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9001 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7349 _diffrn_reflns_av_R_equivalents 0.1197 _diffrn_reflns_av_sigmaI/netI 0.0820 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2792 _reflns_number_gt 2394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1858P)^2^+2.2503P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_number_reflns 2792 _refine_ls_number_parameters 345 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2352 _refine_ls_wR_factor_gt 0.2226 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.927 _refine_ls_shift/su_max 0.004 _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 S1 S 0.92097(15) -0.0576(3) 0.36606(13) 0.0290(5) Uani 1 1 d . . . O1 O 0.8579(4) 0.3107(7) 0.1927(3) 0.0231(10) Uani 1 1 d . . . O2 O 0.7210(4) 0.4908(7) 0.0661(3) 0.0264(11) Uani 1 1 d . . . O3 O 0.8911(4) 0.6113(7) 0.0277(3) 0.0265(11) Uani 1 1 d . . . O4 O 0.8200(8) -0.2635(10) 0.4590(5) 0.068(2) Uani 1 1 d . . . N1 N 0.7893(10) -0.1451(10) 0.4112(5) 0.059(3) Uani 1 1 d . . . C1 C 0.7783(6) 0.2179(10) 0.3610(5) 0.0276(15) Uani 1 1 d . . . H1B H 0.7237 0.1559 0.3974 0.033 Uiso 1 1 calc R . . H1C H 0.7267 0.2966 0.3237 0.033 Uiso 1 1 calc R . . C2 C 0.8732(7) 0.3079(10) 0.4273(5) 0.0320(17) Uani 1 1 d . . . H2A H 0.8300 0.3869 0.4625 0.038 Uiso 1 1 calc R . . H2B H 0.9157 0.2313 0.4716 0.038 Uiso 1 1 calc R . . C3 C 0.9687(7) 0.3943(10) 0.3762(5) 0.0326(16) Uani 1 1 d . . . H3A H 0.9282 0.4808 0.3378 0.039 Uiso 1 1 calc R . . H3B H 1.0323 0.4431 0.4212 0.039 Uiso 1 1 calc R . . C4A C 0.9334(5) 0.1936(9) 0.2470(4) 0.0202(13) Uani 1 1 d . . . C4 C 1.0286(6) 0.2788(9) 0.3161(5) 0.0242(14) Uani 1 1 d . . . H4A H 1.0752 0.1981 0.3554 0.029 Uiso 1 1 calc R . . H4B H 1.0878 0.3372 0.2819 0.029 Uiso 1 1 calc R . . C5 C 0.9923(6) 0.0795(9) 0.1822(5) 0.0250(15) Uani 1 1 d . . . H5A H 1.0378 -0.0052 0.2191 0.030 Uiso 1 1 calc R . . H5B H 1.0523 0.1395 0.1495 0.030 Uiso 1 1 calc R . . C6 C 0.8965(7) 0.0023(11) 0.1116(5) 0.0306(16) Uani 1 1 d . . . H6A H 0.8592 0.0856 0.0692 0.037 Uiso 1 1 calc R . . H6B H 0.9379 -0.0761 0.0748 0.037 Uiso 1 1 calc R . . C7 C 0.7954(7) -0.0816(10) 0.1567(5) 0.0337(18) Uani 1 1 d . . . H7A H 0.8299 -0.1778 0.1895 0.040 Uiso 1 1 calc R . . H7B H 0.7302 -0.1168 0.1084 0.040 Uiso 1 1 calc R . . C8 C 0.7386(6) 0.0271(9) 0.2248(5) 0.0255(15) Uani 1 1 d . . . H8A H 0.6807 -0.0361 0.2576 0.031 Uiso 1 1 calc R . . H8B H 0.6910 0.1125 0.1902 0.031 Uiso 1 1 calc R . . C8A C 0.8360(6) 0.1043(9) 0.2962(5) 0.0220(14) Uani 1 1 d . . . C9 C 0.9216(6) 0.4197(10) 0.1433(5) 0.0294(17) Uani 1 1 d . . . H9A H 0.9823 0.3620 0.1101 0.035 Uiso 1 1 calc R . . H9B H 0.9670 0.4958 0.1864 0.035 Uiso 1 1 calc R . . C10 C 0.8332(6) 0.5101(9) 0.0752(4) 0.0210(13) Uani 1 1 d . . . S1A S 0.58746(16) 0.3967(3) 0.69264(15) 0.0348(5) Uani 1 1 d D . . O1A O 0.6147(4) -0.0569(7) 0.7725(3) 0.0230(10) Uani 1 1 d . A . O2A O 0.7405(5) -0.2372(7) 0.9032(4) 0.0325(12) Uani 1 1 d . . . O3A O 0.5706(5) -0.3745(7) 0.9275(4) 0.0322(12) Uani 1 1 d . . . O4A O 0.6775(8) 0.6426(8) 0.6308(6) 0.0359(19) Uani 0.673(11) 1 d PDU A 1 O4A' O 0.7846(13) 0.4549(19) 0.6223(10) 0.027(2) Uani 0.327(11) 1 d PDU A 2 N1A N 0.7067(11) 0.4927(12) 0.6463(12) 0.0326(19) Uani 0.673(11) 1 d PDU A 1 N1A' N 0.689(2) 0.5281(19) 0.650(3) 0.032(2) Uani 0.327(11) 1 d PDU A 2 C1A C 0.6701(7) 0.1162(11) 0.6179(5) 0.0300(16) Uani 1 1 d . . . H1AA H 0.7092 0.0101 0.6286 0.036 Uiso 1 1 calc R A . H1AB H 0.7263 0.1832 0.5857 0.036 Uiso 1 1 calc R . . C2A C 0.5479(7) 0.0951(11) 0.5548(5) 0.0317(17) Uani 1 1 d . A . H2AA H 0.5152 0.2014 0.5350 0.038 Uiso 1 1 calc R . . H2AB H 0.5637 0.0349 0.4990 0.038 Uiso 1 1 calc R . . C3A C 0.4525(6) 0.0063(11) 0.6040(5) 0.0300(16) Uani 1 1 d . . . H3AA H 0.4792 -0.1058 0.6147 0.036 Uiso 1 1 calc R A . H3AB H 0.3728 0.0054 0.5644 0.036 Uiso 1 1 calc R . . C4A' C 0.4350(6) 0.0851(9) 0.6969(5) 0.0265(15) Uani 1 1 d . A . H4AA H 0.3993 0.1930 0.6857 0.032 Uiso 1 1 calc R . . H4AB H 0.3764 0.0209 0.7286 0.032 Uiso 1 1 calc R . . C4AA C 0.5577(6) 0.0988(8) 0.7591(5) 0.0206(14) Uani 1 1 d . . . C5A C 0.5438(6) 0.1745(10) 0.8528(5) 0.0249(15) Uani 1 1 d . A . H5AA H 0.4836 0.1116 0.8837 0.030 Uiso 1 1 calc R . . H5AB H 0.5106 0.2839 0.8431 0.030 Uiso 1 1 calc R . . C6A C 0.6659(7) 0.1822(11) 0.9158(5) 0.0309(17) Uani 1 1 d . . . H6AA H 0.6527 0.2385 0.9734 0.037 Uiso 1 1 calc R A . H6AB H 0.6942 0.0725 0.9320 0.037 Uiso 1 1 calc R . . C7A C 0.7649(7) 0.2691(10) 0.8691(5) 0.0305(16) Uani 1 1 d . A . H7AA H 0.7433 0.3838 0.8629 0.037 Uiso 1 1 calc R . . H7AB H 0.8446 0.2606 0.9082 0.037 Uiso 1 1 calc R . . C8AA C 0.6554(6) 0.1916(9) 0.7102(5) 0.0225(14) Uani 1 1 d . A . C8A' C 0.7784(6) 0.2004(10) 0.7741(5) 0.0286(16) Uani 1 1 d . . . H8AA H 0.8137 0.0917 0.7816 0.034 Uiso 1 1 calc R A . H8AB H 0.8373 0.2672 0.7442 0.034 Uiso 1 1 calc R . . C9A C 0.5471(7) -0.1751(9) 0.8138(5) 0.0255(15) Uani 1 1 d . . . H9AA H 0.5110 -0.2510 0.7663 0.031 Uiso 1 1 calc R A . H9AB H 0.4789 -0.1245 0.8425 0.031 Uiso 1 1 calc R . . C10A C 0.6300(6) -0.2632(9) 0.8857(5) 0.0230(14) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0216(8) 0.0260(8) 0.0375(9) 0.0113(8) -0.0050(7) 0.0038(7) O1 0.013(2) 0.022(2) 0.032(2) 0.013(2) -0.0055(18) 0.0004(19) O2 0.018(2) 0.025(3) 0.035(2) 0.008(2) -0.0032(19) 0.0006(19) O3 0.019(2) 0.025(3) 0.035(2) 0.012(2) 0.0016(19) 0.000(2) O4 0.097(6) 0.048(4) 0.052(4) 0.018(4) -0.023(4) -0.042(4) N1 0.109(7) 0.034(4) 0.030(3) 0.005(3) -0.013(4) -0.037(5) C1 0.020(3) 0.030(4) 0.033(3) 0.004(3) 0.003(3) 0.006(3) C2 0.036(4) 0.028(4) 0.034(4) 0.000(3) 0.009(3) 0.008(3) C3 0.033(4) 0.021(3) 0.040(4) 0.000(3) -0.011(3) -0.004(3) C4A 0.011(3) 0.022(3) 0.027(3) 0.009(3) -0.003(2) 0.002(3) C4 0.017(3) 0.026(3) 0.029(3) 0.011(3) -0.001(3) -0.004(3) C5 0.014(3) 0.023(3) 0.037(3) 0.005(3) -0.001(3) 0.002(3) C6 0.029(4) 0.034(4) 0.029(3) -0.006(3) 0.002(3) -0.002(3) C7 0.027(3) 0.033(4) 0.039(4) -0.007(4) -0.006(3) -0.007(3) C8 0.014(3) 0.026(4) 0.035(3) 0.008(3) -0.002(3) -0.002(3) C8A 0.015(3) 0.019(3) 0.030(3) 0.005(3) -0.003(3) 0.001(3) C9 0.022(3) 0.030(4) 0.035(3) 0.018(3) -0.003(3) -0.003(3) C10 0.022(3) 0.017(3) 0.024(3) -0.001(3) 0.002(3) 0.002(3) S1A 0.0233(8) 0.0250(9) 0.0553(12) 0.0084(9) 0.0000(8) -0.0009(7) O1A 0.015(2) 0.016(2) 0.036(2) 0.007(2) -0.0045(18) 0.0019(19) O2A 0.023(2) 0.031(3) 0.042(3) 0.017(3) -0.005(2) 0.003(2) O3A 0.025(2) 0.032(3) 0.039(3) 0.016(3) 0.000(2) 0.002(2) O4A 0.042(4) 0.015(3) 0.046(4) 0.014(3) -0.013(3) -0.013(3) O4A' 0.026(4) 0.016(4) 0.037(5) 0.007(5) -0.006(4) -0.005(4) N1A 0.033(4) 0.018(3) 0.044(3) 0.007(4) -0.008(3) -0.001(3) N1A' 0.033(4) 0.018(4) 0.043(4) 0.006(4) -0.007(3) -0.001(4) C1A 0.024(3) 0.033(4) 0.032(3) 0.009(3) -0.001(3) -0.005(3) C2A 0.028(4) 0.033(4) 0.032(3) 0.004(3) -0.005(3) -0.008(3) C3A 0.022(3) 0.033(4) 0.032(3) -0.001(3) -0.009(3) -0.007(3) C4A' 0.015(3) 0.026(3) 0.036(4) 0.011(3) -0.009(3) -0.004(3) C4AA 0.013(3) 0.015(3) 0.032(3) 0.001(3) -0.005(3) 0.002(2) C5A 0.018(3) 0.027(3) 0.029(3) 0.004(3) 0.000(3) -0.006(3) C6A 0.031(4) 0.035(4) 0.025(3) -0.007(3) -0.004(3) -0.004(3) C7A 0.025(3) 0.030(4) 0.034(3) -0.002(3) -0.008(3) -0.008(3) C8AA 0.012(3) 0.018(3) 0.035(3) 0.004(3) -0.004(3) -0.003(3) C8A' 0.012(3) 0.027(4) 0.045(4) 0.000(3) -0.006(3) -0.004(3) C9A 0.024(3) 0.020(3) 0.032(3) 0.011(3) 0.000(3) -0.005(3) C10A 0.020(3) 0.017(3) 0.030(3) 0.005(3) -0.002(3) 0.001(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 S1 N1 1.804(10) . ? S1 C8A 1.879(7) . ? O1 C9 1.397(8) . ? O1 C4A 1.458(8) . ? O2 C10 1.229(8) . ? O3 C10 1.303(8) . ? O4 N1 1.237(11) . ? C1 C8A 1.527(10) . ? C1 C2 1.535(11) . ? C2 C3 1.532(11) . ? C3 C4 1.504(11) . ? C4A C5 1.537(10) . ? C4A C8A 1.542(9) . ? C4A C4 1.542(9) . ? C5 C6 1.528(10) . ? C6 C7 1.521(11) . ? C7 C8 1.530(11) . ? C8 C8A 1.546(9) . ? C9 C10 1.510(9) . ? S1A N1A 1.732(8) . ? S1A N1A' 1.733(8) . ? S1A C8AA 1.877(7) . ? O1A C9A 1.411(8) . ? O1A C4AA 1.449(8) . ? O2A C10A 1.226(8) . ? O3A C10A 1.324(9) . ? O4A N1A 1.308(13) . ? O4A' N1A' 1.308(13) . ? C1A C8AA 1.514(11) . ? C1A C2A 1.546(10) . ? C2A C3A 1.526(10) . ? C3A C4A' 1.540(11) . ? C4A' C4AA 1.538(8) . ? C4AA C5A 1.532(10) . ? C4AA C8AA 1.558(9) . ? C5A C6A 1.535(9) . ? C6A C7A 1.527(11) . ? C7A C8A' 1.525(11) . ? C8AA C8A' 1.550(8) . ? C9A C10A 1.503(9) . ? 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 N1 S1 C8A 97.3(4) . . ? C9 O1 C4A 115.9(5) . . ? O4 N1 S1 110.8(9) . . ? C8A C1 C2 113.6(6) . . ? C3 C2 C1 111.9(6) . . ? C4 C3 C2 110.3(6) . . ? O1 C4A C5 109.4(5) . . ? O1 C4A C8A 101.6(5) . . ? C5 C4A C8A 110.2(6) . . ? O1 C4A C4 110.2(6) . . ? C5 C4A C4 113.1(5) . . ? C8A C4A C4 111.7(5) . . ? C3 C4 C4A 112.0(6) . . ? C4A C5 C6 112.1(6) . . ? C7 C6 C5 112.3(6) . . ? C6 C7 C8 112.0(6) . . ? C7 C8 C8A 112.9(5) . . ? C1 C8A C4A 110.0(6) . . ? C1 C8A C8 112.2(5) . . ? C4A C8A C8 110.3(5) . . ? C1 C8A S1 109.0(5) . . ? C4A C8A S1 106.2(4) . . ? C8 C8A S1 109.0(5) . . ? O1 C9 C10 110.4(5) . . ? O2 C10 O3 124.5(6) . . ? O2 C10 C9 124.2(6) . . ? O3 C10 C9 111.4(5) . . ? N1A S1A N1A' 11.8(9) . . ? N1A S1A C8AA 100.1(5) . . ? N1A' S1A C8AA 111.7(7) . . ? C9A O1A C4AA 116.8(5) . . ? O4A N1A S1A 109.5(8) . . ? O4A' N1A' S1A 112.3(12) . . ? C8AA C1A C2A 114.1(6) . . ? C3A C2A C1A 111.3(6) . . ? C2A C3A C4A' 111.5(6) . . ? C4AA C4A' C3A 111.6(6) . . ? O1A C4AA C5A 109.6(5) . . ? O1A C4AA C4A' 110.2(5) . . ? C5A C4AA C4A' 113.1(6) . . ? O1A C4AA C8AA 101.8(5) . . ? C5A C4AA C8AA 110.3(5) . . ? C4A' C4AA C8AA 111.3(5) . . ? C4AA C5A C6A 112.8(6) . . ? C7A C6A C5A 111.3(6) . . ? C8A' C7A C6A 111.9(6) . . ? C1A C8AA C8A' 112.7(6) . . ? C1A C8AA C4AA 110.3(6) . . ? C8A' C8AA C4AA 109.9(6) . . ? C1A C8AA S1A 109.8(5) . . ? C8A' C8AA S1A 110.0(5) . . ? C4AA C8AA S1A 103.8(4) . . ? C7A C8A' C8AA 113.6(6) . . ? O1A C9A C10A 109.9(5) . . ? O2A C10A O3A 123.5(6) . . ? O2A C10A C9A 124.2(6) . . ? O3A C10A C9A 112.4(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 C8A S1 N1 O4 177.4(6) . . . . ? C8A C1 C2 C3 53.2(9) . . . . ? C1 C2 C3 C4 -54.4(8) . . . . ? C9 O1 C4A C5 -67.4(7) . . . . ? C9 O1 C4A C8A 176.1(6) . . . . ? C9 O1 C4A C4 57.6(8) . . . . ? C2 C3 C4 C4A 56.9(8) . . . . ? O1 C4A C4 C3 55.0(7) . . . . ? C5 C4A C4 C3 177.8(6) . . . . ? C8A C4A C4 C3 -57.2(7) . . . . ? O1 C4A C5 C6 -54.2(8) . . . . ? C8A C4A C5 C6 56.8(7) . . . . ? C4 C4A C5 C6 -177.4(6) . . . . ? C4A C5 C6 C7 -54.5(8) . . . . ? C5 C6 C7 C8 51.4(8) . . . . ? C6 C7 C8 C8A -52.0(8) . . . . ? C2 C1 C8A C4A -51.8(8) . . . . ? C2 C1 C8A C8 -174.9(6) . . . . ? C2 C1 C8A S1 64.2(7) . . . . ? O1 C4A C8A C1 -64.4(6) . . . . ? C5 C4A C8A C1 179.6(5) . . . . ? C4 C4A C8A C1 53.0(7) . . . . ? O1 C4A C8A C8 59.9(7) . . . . ? C5 C4A C8A C8 -56.1(7) . . . . ? C4 C4A C8A C8 177.3(6) . . . . ? O1 C4A C8A S1 177.8(4) . . . . ? C5 C4A C8A S1 61.9(5) . . . . ? C4 C4A C8A S1 -64.7(6) . . . . ? C7 C8 C8A C1 177.6(6) . . . . ? C7 C8 C8A C4A 54.5(8) . . . . ? C7 C8 C8A S1 -61.6(7) . . . . ? N1 S1 C8A C1 63.6(5) . . . . ? N1 S1 C8A C4A -178.0(5) . . . . ? N1 S1 C8A C8 -59.2(5) . . . . ? C4A O1 C9 C10 168.0(6) . . . . ? O1 C9 C10 O2 0.9(10) . . . . ? O1 C9 C10 O3 -179.3(6) . . . . ? N1A' S1A N1A O4A -9(8) . . . . ? C8AA S1A N1A O4A -178.5(11) . . . . ? N1A S1A N1A' O4A' 0(7) . . . . ? C8AA S1A N1A' O4A' 11(3) . . . . ? C8AA C1A C2A C3A -52.9(9) . . . . ? C1A C2A C3A C4A' 52.8(9) . . . . ? C2A C3A C4A' C4AA -55.6(8) . . . . ? C9A O1A C4AA C5A 65.1(7) . . . . ? C9A O1A C4AA C4A' -60.0(8) . . . . ? C9A O1A C4AA C8AA -178.2(5) . . . . ? C3A C4A' C4AA O1A -56.0(8) . . . . ? C3A C4A' C4AA C5A -179.2(6) . . . . ? C3A C4A' C4AA C8AA 56.1(8) . . . . ? O1A C4AA C5A C6A 54.5(7) . . . . ? C4A' C4AA C5A C6A 178.0(6) . . . . ? C8AA C4AA C5A C6A -56.7(7) . . . . ? C4AA C5A C6A C7A 55.2(9) . . . . ? C5A C6A C7A C8A' -52.1(9) . . . . ? C2A C1A C8AA C8A' 176.2(6) . . . . ? C2A C1A C8AA C4AA 53.0(8) . . . . ? C2A C1A C8AA S1A -60.8(7) . . . . ? O1A C4AA C8AA C1A 63.2(6) . . . . ? C5A C4AA C8AA C1A 179.5(6) . . . . ? C4A' C4AA C8AA C1A -54.1(7) . . . . ? O1A C4AA C8AA C8A' -61.6(7) . . . . ? C5A C4AA C8AA C8A' 54.7(7) . . . . ? C4A' C4AA C8AA C8A' -179.0(6) . . . . ? O1A C4AA C8AA S1A -179.1(4) . . . . ? C5A C4AA C8AA S1A -62.9(5) . . . . ? C4A' C4AA C8AA S1A 63.5(6) . . . . ? N1A S1A C8AA C1A -66.2(8) . . . . ? N1A' S1A C8AA C1A -68.5(15) . . . . ? N1A S1A C8AA C8A' 58.3(8) . . . . ? N1A' S1A C8AA C8A' 56.0(15) . . . . ? N1A S1A C8AA C4AA 175.8(7) . . . . ? N1A' S1A C8AA C4AA 173.5(15) . . . . ? C6A C7A C8A' C8AA 52.9(9) . . . . ? C1A C8AA C8A' C7A -177.4(6) . . . . ? C4AA C8AA C8A' C7A -53.9(8) . . . . ? S1A C8AA C8A' C7A 59.7(7) . . . . ? C4AA O1A C9A C10A -135.5(6) . . . . ? O1A C9A C10A O2A -1.7(10) . . . . ? O1A C9A C10A O3A 179.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.436 _refine_diff_density_min -1.036 _refine_diff_density_rms 0.120