# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_kaw131 _database_code_depnum_ccdc_archive 'CCDC 895728' #TrackingRef '- wheeler-ChemComm13.CIF' # (rac)-1-I, unreacted _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O6 S' _chemical_formula_sum 'C18 H17 N O6 S' _chemical_formula_weight 375.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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' _symmetry_space_group_name_Hall '-P 2yn' 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 15.5367(3) _cell_length_b 7.2065(1) _cell_length_c 15.8326(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.567(1) _cell_angle_gamma 90.00 _cell_volume 1699.11(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8176 _cell_measurement_theta_min 3.516 _cell_measurement_theta_max 67.004 _exptl_crystal_description 'transparent lathe' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 2.024 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4689 _exptl_absorpt_correction_T_max 0.8614 _exptl_absorpt_process_details 'SADABS (Bruker, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 23203 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 67.60 _reflns_number_total 3054 _reflns_number_gt 2717 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2008) and XPREP (Bruker, 2008) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _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. All non-hydrogen atoms were located in a single difference Fourier map and refined with anisotropic thermal parameters. The N-H and O-H hydrogen atoms were located in difference density Fourier maps and refined with Uiso = 1.2Ueq of the corresponding O/N atoms. All other H atoms were place in calculated positions and refined with Uiso = 1.2Ueq of the corresponding C atom (Uiso = 1.5eq for methyl C-H groups). ; _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^)+(0.0549P)^2^+1.5442P] 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 3054 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.45901(3) 0.21762(7) 0.58776(3) 0.02476(16) Uani 1 1 d . . . O1 O -0.12848(11) 0.2220(2) 0.42690(10) 0.0331(4) Uani 1 1 d . . . H4 H -0.185(2) 0.198(4) 0.4145(17) 0.040 Uiso 1 1 d . . . O2 O -0.14028(10) 0.0475(2) 0.30709(10) 0.0321(4) Uani 1 1 d . . . O3 O 0.31420(10) -0.0118(2) 0.73919(10) 0.0331(4) Uani 1 1 d . . . H7 H 0.2551(19) -0.033(4) 0.7231(17) 0.040 Uiso 1 1 d . . . O4 O 0.30583(10) -0.1636(2) 0.61344(10) 0.0327(4) Uani 1 1 d . . . O5 O 0.48748(10) 0.3412(2) 0.66039(10) 0.0311(4) Uani 1 1 d . . . O6 O 0.49820(10) 0.2295(2) 0.51604(10) 0.0315(4) Uani 1 1 d . . . N1 N 0.47867(12) 0.0072(3) 0.62507(12) 0.0276(4) Uani 1 1 d . . . H1 H 0.4734(17) -0.072(4) 0.5844(17) 0.033 Uiso 1 1 d . . . C1 C -0.09500(14) 0.1366(3) 0.37015(14) 0.0264(5) Uani 1 1 d . . . C2 C 0.00320(14) 0.1499(3) 0.38760(14) 0.0280(5) Uani 1 1 d . . . H2 H 0.0294 0.1046 0.3443 0.034 Uiso 1 1 calc R . . C3 C 0.05665(14) 0.2222(3) 0.46094(14) 0.0274(5) Uani 1 1 d . . . H3 H 0.0282 0.2744 0.5012 0.033 Uiso 1 1 calc R . . C4 C 0.15536(14) 0.2299(3) 0.48650(14) 0.0257(5) Uani 1 1 d . . . C5 C 0.19966(14) 0.3194(3) 0.56487(14) 0.0275(5) Uani 1 1 d . . . H5 H 0.1656 0.3775 0.5986 0.033 Uiso 1 1 calc R . . C6 C 0.29265(14) 0.3251(3) 0.59429(14) 0.0263(5) Uani 1 1 d . . . H6 H 0.3225 0.3871 0.6475 0.032 Uiso 1 1 calc R . . C7 C 0.34104(13) 0.2385(3) 0.54444(14) 0.0240(4) Uani 1 1 d . . . C8 C 0.29859(14) 0.1507(3) 0.46502(14) 0.0264(5) Uani 1 1 d . . . H8 H 0.3329 0.0939 0.4312 0.032 Uiso 1 1 calc R . . C9 C 0.20587(14) 0.1473(3) 0.43627(14) 0.0271(5) Uani 1 1 d . . . H9 H 0.1762 0.0886 0.3821 0.033 Uiso 1 1 calc R . . C10 C 0.34795(14) -0.0789(3) 0.67889(14) 0.0273(5) Uani 1 1 d . . . C11 C 0.44961(14) -0.0505(3) 0.70059(14) 0.0274(5) Uani 1 1 d . . . H11 H 0.4685 0.0454 0.7479 0.033 Uiso 1 1 calc R . . C12 C 0.49204(14) -0.2367(3) 0.73651(16) 0.0311(5) Uani 1 1 d . . . H12A H 0.4644 -0.2807 0.7820 0.037 Uiso 1 1 calc R . . H12B H 0.4777 -0.3286 0.6880 0.037 Uiso 1 1 calc R . . C13 C 0.59307(14) -0.2300(3) 0.77623(14) 0.0247(4) Uani 1 1 d . . . C14 C 0.63016(15) -0.1543(3) 0.85954(14) 0.0293(5) Uani 1 1 d . . . H14 H 0.5919 -0.1041 0.8910 0.035 Uiso 1 1 calc R . . C15 C 0.72215(15) -0.1515(3) 0.89705(15) 0.0315(5) Uani 1 1 d . . . H15 H 0.7468 -0.0990 0.9539 0.038 Uiso 1 1 calc R . . C16 C 0.77829(14) -0.2254(3) 0.85173(15) 0.0310(5) Uani 1 1 d . . . H16 H 0.8415 -0.2229 0.8773 0.037 Uiso 1 1 calc R . . C17 C 0.74235(15) -0.3026(3) 0.76949(15) 0.0302(5) Uani 1 1 d . . . H17 H 0.7809 -0.3540 0.7386 0.036 Uiso 1 1 calc R . . C18 C 0.64990(15) -0.3052(3) 0.73182(14) 0.0285(5) Uani 1 1 d . . . H18 H 0.6255 -0.3590 0.6752 0.034 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 0.0183(3) 0.0270(3) 0.0284(3) -0.0016(2) 0.0058(2) -0.00103(19) O1 0.0212(8) 0.0435(10) 0.0346(9) -0.0065(7) 0.0078(7) -0.0009(7) O2 0.0228(7) 0.0421(9) 0.0318(8) -0.0044(7) 0.0083(6) -0.0016(7) O3 0.0208(8) 0.0466(10) 0.0321(8) 0.0007(7) 0.0080(6) 0.0008(7) O4 0.0221(8) 0.0431(9) 0.0327(8) -0.0021(7) 0.0074(6) -0.0012(7) O5 0.0236(7) 0.0354(9) 0.0322(8) -0.0053(7) 0.0046(6) -0.0009(6) O6 0.0242(7) 0.0384(9) 0.0332(9) -0.0045(7) 0.0106(6) -0.0022(6) N1 0.0226(9) 0.0321(11) 0.0282(10) -0.0040(8) 0.0074(7) 0.0013(7) C1 0.0237(11) 0.0292(11) 0.0269(11) 0.0042(9) 0.0081(9) 0.0021(9) C2 0.0243(11) 0.0311(12) 0.0298(11) 0.0007(9) 0.0099(9) 0.0006(9) C3 0.0259(11) 0.0286(11) 0.0290(11) 0.0026(9) 0.0100(9) 0.0025(9) C4 0.0231(10) 0.0265(11) 0.0269(11) 0.0040(8) 0.0060(8) 0.0010(8) C5 0.0259(11) 0.0297(12) 0.0282(11) 0.0008(9) 0.0097(9) 0.0030(9) C6 0.0256(11) 0.0280(11) 0.0244(10) -0.0006(9) 0.0056(8) -0.0001(9) C7 0.0188(10) 0.0243(11) 0.0279(11) 0.0023(8) 0.0050(8) 0.0002(8) C8 0.0257(11) 0.0269(11) 0.0278(11) -0.0023(9) 0.0096(8) -0.0007(9) C9 0.0254(11) 0.0286(11) 0.0258(10) -0.0021(9) 0.0048(8) -0.0028(9) C10 0.0236(11) 0.0302(12) 0.0268(11) 0.0057(9) 0.0049(9) 0.0013(9) C11 0.0214(10) 0.0316(12) 0.0280(11) 0.0020(9) 0.0052(8) 0.0005(9) C12 0.0229(11) 0.0287(12) 0.0397(13) 0.0015(10) 0.0059(9) -0.0013(9) C13 0.0213(10) 0.0213(10) 0.0304(11) 0.0053(8) 0.0057(8) -0.0002(8) C14 0.0290(11) 0.0295(12) 0.0317(11) 0.0014(9) 0.0122(9) 0.0030(9) C15 0.0339(12) 0.0300(12) 0.0270(11) 0.0001(9) 0.0027(9) -0.0019(9) C16 0.0198(10) 0.0290(12) 0.0408(13) 0.0076(10) 0.0034(9) -0.0007(9) C17 0.0277(11) 0.0289(12) 0.0377(12) 0.0031(9) 0.0150(9) 0.0036(9) C18 0.0297(11) 0.0283(12) 0.0260(11) -0.0004(9) 0.0059(9) -0.0004(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 S1 O5 1.4218(16) . ? S1 O6 1.4358(15) . ? S1 N1 1.624(2) . ? S1 C7 1.771(2) . ? O1 C1 1.313(3) . ? O1 H4 0.87(3) . ? O2 C1 1.226(3) . ? O3 C10 1.306(3) . ? O3 H7 0.89(3) . ? O4 C10 1.220(3) . ? N1 C11 1.454(3) . ? N1 H1 0.85(3) . ? C1 C2 1.474(3) . ? C2 C3 1.326(3) . ? C2 H2 0.9500 . ? C3 C4 1.471(3) . ? C3 H3 0.9500 . ? C4 C5 1.394(3) . ? C4 C9 1.399(3) . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 C7 1.384(3) . ? C6 H6 0.9500 . ? C7 C8 1.394(3) . ? C8 C9 1.382(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.531(3) . ? C11 C12 1.531(3) . ? C11 H11 1.0000 . ? C12 C13 1.516(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.386(3) . ? C13 C14 1.391(3) . ? C14 C15 1.383(3) . ? C14 H14 0.9500 . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 C17 1.379(3) . ? C16 H16 0.9500 . ? C17 C18 1.389(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 S1 O6 119.86(9) . . ? O5 S1 N1 107.92(10) . . ? O6 S1 N1 105.37(10) . . ? O5 S1 C7 108.00(9) . . ? O6 S1 C7 108.32(10) . . ? N1 S1 C7 106.66(10) . . ? C1 O1 H4 109.1(18) . . ? C10 O3 H7 108.8(17) . . ? C11 N1 S1 119.74(15) . . ? C11 N1 H1 116.5(18) . . ? S1 N1 H1 112.7(18) . . ? O2 C1 O1 123.74(19) . . ? O2 C1 C2 120.64(19) . . ? O1 C1 C2 115.61(19) . . ? C3 C2 C1 123.1(2) . . ? C3 C2 H2 118.5 . . ? C1 C2 H2 118.5 . . ? C2 C3 C4 126.8(2) . . ? C2 C3 H3 116.6 . . ? C4 C3 H3 116.6 . . ? C5 C4 C9 119.23(19) . . ? C5 C4 C3 118.27(19) . . ? C9 C4 C3 122.48(19) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 118.60(19) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C6 C7 C8 121.65(19) . . ? C6 C7 S1 119.21(16) . . ? C8 C7 S1 118.81(16) . . ? C9 C8 C7 119.06(19) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C4 120.41(19) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? O4 C10 O3 125.19(19) . . ? O4 C10 C11 121.78(19) . . ? O3 C10 C11 112.95(18) . . ? N1 C11 C12 110.76(18) . . ? N1 C11 C10 113.32(17) . . ? C12 C11 C10 105.87(17) . . ? N1 C11 H11 108.9 . . ? C12 C11 H11 108.9 . . ? C10 C11 H11 108.9 . . ? C13 C12 C11 114.27(18) . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C18 C13 C14 118.85(19) . . ? C18 C13 C12 120.72(19) . . ? C14 C13 C12 120.39(19) . . ? C15 C14 C13 120.7(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 119.9(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.1(2) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C13 C18 C17 120.5(2) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? 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 O5 S1 N1 C11 49.15(18) . . . . ? O6 S1 N1 C11 178.32(15) . . . . ? C7 S1 N1 C11 -66.69(18) . . . . ? O2 C1 C2 C3 -170.4(2) . . . . ? O1 C1 C2 C3 8.2(3) . . . . ? C1 C2 C3 C4 175.6(2) . . . . ? C2 C3 C4 C5 177.2(2) . . . . ? C2 C3 C4 C9 -4.4(4) . . . . ? C9 C4 C5 C6 -1.1(3) . . . . ? C3 C4 C5 C6 177.45(19) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C5 C6 C7 C8 1.6(3) . . . . ? C5 C6 C7 S1 -171.76(16) . . . . ? O5 S1 C7 C6 -15.5(2) . . . . ? O6 S1 C7 C6 -146.69(17) . . . . ? N1 S1 C7 C6 100.33(18) . . . . ? O5 S1 C7 C8 171.00(16) . . . . ? O6 S1 C7 C8 39.8(2) . . . . ? N1 S1 C7 C8 -73.22(19) . . . . ? C6 C7 C8 C9 -1.2(3) . . . . ? S1 C7 C8 C9 172.21(16) . . . . ? C7 C8 C9 C4 -0.4(3) . . . . ? C5 C4 C9 C8 1.5(3) . . . . ? C3 C4 C9 C8 -176.9(2) . . . . ? S1 N1 C11 C12 -167.82(14) . . . . ? S1 N1 C11 C10 73.4(2) . . . . ? O4 C10 C11 N1 45.6(3) . . . . ? O3 C10 C11 N1 -137.6(2) . . . . ? O4 C10 C11 C12 -76.0(3) . . . . ? O3 C10 C11 C12 100.8(2) . . . . ? N1 C11 C12 C13 66.4(2) . . . . ? C10 C11 C12 C13 -170.37(18) . . . . ? C11 C12 C13 C18 -105.8(2) . . . . ? C11 C12 C13 C14 76.7(3) . . . . ? C18 C13 C14 C15 0.9(3) . . . . ? C12 C13 C14 C15 178.5(2) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 -0.4(3) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C14 C13 C18 C17 -0.9(3) . . . . ? C12 C13 C18 C17 -178.5(2) . . . . ? C16 C17 C18 C13 0.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H4 O4 0.87(3) 1.81(3) 2.678(2) 176(3) 3_556 O3 H7 O2 0.89(3) 1.71(3) 2.603(2) 174(3) 3_556 N1 H1 O6 0.85(3) 2.10(3) 2.914(2) 161(2) 3_656 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 67.60 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.481 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.062 data_kaw128 _database_code_depnum_ccdc_archive 'CCDC 895729' #TrackingRef '- wheeler-ChemComm13.CIF' # (rac)-1-I, reacted _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O6 S' _chemical_formula_sum 'C18 H17 N O6 S' _chemical_formula_weight 375.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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' _symmetry_space_group_name_Hall '-P 2yn' 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 15.3346(8) _cell_length_b 7.2910(4) _cell_length_c 16.1284(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.857(4) _cell_angle_gamma 90.00 _cell_volume 1742.94(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7088 _cell_measurement_theta_min 3.437 _cell_measurement_theta_max 66.504 _exptl_crystal_description 'transparent lathe' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 1.973 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4517 _exptl_absorpt_correction_T_max 0.7228 _exptl_absorpt_process_details 'SADABS (Bruker, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 10334 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 67.67 _reflns_number_total 3003 _reflns_number_gt 1693 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2008) and XPREP (Bruker, 2008) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _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. All non-hydrogen atoms were located in a single difference Fourier map and refined with anisotropic thermal parameters. UV irradiation of this sample for 18hrs produced a crystal consisting of both reactant and product phases. This disorder and reaction conversion was modeled using occupancy factors to give a 67:33 ratio of reactant to photoproduct. The aryl groups of the product phase were restrained to be similar to aryl groups of the reactant phases using the SAME command. The N-H and O-H hydrogen atoms were located in difference density Fourier maps and refined with the O/N-H bonds restrained to 0.85(2) angstroms and Uiso = 1.2Ueq of the corresponding O/N atoms. All other H atoms were place in calculated positions and refined with Uiso = 1.2Ueq of the corresponding C atom (Uiso = 1.5eq for methyl C-H groups). ; _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^)+(0.1125P)^2^+0.0693P] 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 3003 _refine_ls_number_parameters 303 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1180 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.2032 _refine_ls_wR_factor_gt 0.1650 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.022 _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 0.45699(7) 0.79046(17) 0.08862(7) 0.0716(4) Uani 1 1 d . A . O1 O -0.1312(2) 0.7669(5) -0.0789(2) 0.0945(11) Uani 1 1 d D A . O2 O -0.1336(2) 0.9440(6) -0.1912(2) 0.1006(12) Uani 1 1 d D A . H2 H -0.1878 0.9597 -0.1908 0.121 Uiso 1 1 calc RD . . O3 O 0.3091(2) 1.0379(7) 0.2337(2) 0.1038(13) Uani 1 1 d . . . O4 O 0.3117(2) 1.1875(6) 0.1132(2) 0.1026(12) Uani 1 1 d D . . H4 H 0.2564 1.1992 0.1098 0.123 Uiso 1 1 calc RD . . O5 O 0.4825(2) 0.6700(5) 0.1587(2) 0.0849(10) Uani 1 1 d . . . O6 O 0.4977(2) 0.7768(5) 0.0190(2) 0.0867(10) Uani 1 1 d . . . N1 N 0.4777(2) 0.9976(6) 0.1248(2) 0.0727(10) Uani 1 1 d D . . H1 H 0.469(3) 1.084(5) 0.090(2) 0.087 Uiso 1 1 d D . . C1 C -0.0938(3) 0.8605(7) -0.1257(3) 0.0751(13) Uani 1 1 d . . . C2 C 0.0069(4) 0.8480(10) -0.1085(4) 0.069(2) Uani 0.686(10) 1 d P A 1 H7 H 0.0347 0.8954 -0.1502 0.083 Uiso 0.686(10) 1 calc PR A 1 C3 C 0.0574(4) 0.7763(10) -0.0399(5) 0.0646(18) Uani 0.686(10) 1 d P A 1 H3 H 0.0270 0.7198 -0.0022 0.078 Uiso 0.686(10) 1 calc PR A 1 C4 C 0.1564(5) 0.7714(12) -0.0128(5) 0.063(2) Uani 0.686(10) 1 d PD A 1 C5 C 0.2106(6) 0.8532(12) -0.0597(6) 0.066(2) Uani 0.686(10) 1 d PD A 1 H5 H 0.1830 0.9123 -0.1124 0.080 Uiso 0.686(10) 1 calc PR A 1 C6 C 0.3042(7) 0.8501(17) -0.0310(8) 0.066(3) Uani 0.686(10) 1 d PD A 1 H6 H 0.3415 0.8981 -0.0646 0.079 Uiso 0.686(10) 1 calc PR A 1 C7 C 0.3396(3) 0.7747(7) 0.0477(3) 0.0721(12) Uani 1 1 d . . . C8 C 0.2913(8) 0.688(3) 0.0932(9) 0.068(4) Uani 0.686(10) 1 d PD A 1 H8 H 0.3200 0.6309 0.1461 0.082 Uiso 0.686(10) 1 calc PR A 1 C9 C 0.1978(8) 0.6817(15) 0.0618(6) 0.063(3) Uani 0.686(10) 1 d PD A 1 H9 H 0.1626 0.6151 0.0921 0.075 Uiso 0.686(10) 1 calc PR A 1 C10 C 0.3483(3) 1.0968(8) 0.1791(3) 0.0783(13) Uani 1 1 d . . . C11 C 0.4488(3) 1.0608(7) 0.1976(3) 0.0765(13) Uani 1 1 d . . . H11 H 0.4649 0.9651 0.2434 0.092 Uiso 1 1 calc R . . C12 C 0.4949(3) 1.2383(7) 0.2333(3) 0.0870(15) Uani 1 1 d . . . H12A H 0.4649 1.2871 0.2762 0.104 Uiso 1 1 calc R . . H12B H 0.4860 1.3288 0.1861 0.104 Uiso 1 1 calc R . . C13 C 0.5956(3) 1.2214(7) 0.2752(3) 0.0730(12) Uani 1 1 d . . . C14 C 0.6576(4) 1.2898(8) 0.2361(3) 0.0888(14) Uani 1 1 d . . . H14 H 0.6374 1.3442 0.1810 0.107 Uiso 1 1 calc R . . C15 C 0.7480(4) 1.2821(9) 0.2742(4) 0.1027(17) Uani 1 1 d . . . H15 H 0.7900 1.3309 0.2458 0.123 Uiso 1 1 calc R . . C16 C 0.7776(4) 1.2038(9) 0.3532(5) 0.1021(18) Uani 1 1 d . . . H16 H 0.8405 1.1964 0.3796 0.123 Uiso 1 1 calc R . . C17 C 0.7179(4) 1.1369(9) 0.3939(3) 0.1030(19) Uani 1 1 d . . . H17 H 0.7388 1.0843 0.4494 0.124 Uiso 1 1 calc R . . C18 C 0.6257(3) 1.1443(8) 0.3553(3) 0.0902(15) Uani 1 1 d . . . H18 H 0.5839 1.0964 0.3841 0.108 Uiso 1 1 calc R . . C2A C -0.0183(10) 0.967(3) -0.0697(11) 0.086(6) Uani 0.314(10) 1 d P . 2 H2A H 0.0216 1.0148 -0.1050 0.103 Uiso 0.314(10) 1 calc PR A 2 C3A C 0.0394(11) 0.871(3) 0.0100(12) 0.089(6) Uani 0.314(10) 1 d P . 2 H3A H 0.0090 0.7555 0.0210 0.106 Uiso 0.314(10) 1 calc PR A 2 C4A C 0.1418(13) 0.832(3) 0.0181(13) 0.080(6) Uani 0.314(10) 1 d PD A 2 C5A C 0.1910(13) 0.911(3) -0.0339(15) 0.084(7) Uani 0.314(10) 1 d PD A 2 H5A H 0.1603 0.9752 -0.0842 0.101 Uiso 0.314(10) 1 calc PR A 2 C6A C 0.2850(13) 0.898(4) -0.0132(16) 0.066(6) Uani 0.314(10) 1 d PD A 2 H6A H 0.3157 0.9784 -0.0424 0.079 Uiso 0.314(10) 1 calc PR A 2 C8A C 0.277(2) 0.691(6) 0.100(3) 0.102(16) Uani 0.314(10) 1 d PD A 2 H8A H 0.3041 0.6111 0.1453 0.123 Uiso 0.314(10) 1 calc PR A 2 C9A C 0.1844(19) 0.723(4) 0.0853(14) 0.078(8) Uani 0.314(10) 1 d PD A 2 H9A H 0.1516 0.6694 0.1218 0.094 Uiso 0.314(10) 1 calc PR A 2 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 0.0633(6) 0.0718(7) 0.0763(7) 0.0112(6) 0.0117(5) 0.0005(6) O1 0.0659(19) 0.109(3) 0.106(2) 0.017(2) 0.0160(18) 0.0018(19) O2 0.0641(18) 0.149(4) 0.089(2) 0.018(2) 0.0201(17) 0.004(2) O3 0.071(2) 0.162(4) 0.082(2) 0.009(2) 0.0240(17) 0.002(2) O4 0.0605(18) 0.140(3) 0.105(2) 0.022(2) 0.0163(18) 0.014(2) O5 0.0718(19) 0.085(2) 0.093(2) 0.0230(18) 0.0122(16) 0.0035(17) O6 0.086(2) 0.091(3) 0.085(2) 0.0111(18) 0.0253(17) 0.0040(19) N1 0.061(2) 0.076(3) 0.078(2) 0.0131(19) 0.0127(17) -0.0004(19) C1 0.058(2) 0.090(4) 0.077(3) -0.001(2) 0.016(2) -0.005(2) C2 0.055(3) 0.077(5) 0.079(4) 0.003(3) 0.024(3) 0.004(3) C3 0.058(3) 0.061(4) 0.075(4) -0.003(3) 0.017(3) 0.002(3) C4 0.053(4) 0.059(5) 0.072(5) -0.009(4) 0.008(3) 0.000(3) C5 0.065(5) 0.067(6) 0.063(4) 0.010(4) 0.008(4) 0.005(4) C6 0.067(5) 0.067(7) 0.068(5) 0.008(4) 0.023(4) 0.003(5) C7 0.070(3) 0.074(3) 0.067(2) 0.012(2) 0.008(2) -0.011(2) C8 0.055(5) 0.082(10) 0.062(6) 0.009(6) 0.005(4) 0.003(6) C9 0.052(5) 0.070(6) 0.069(6) -0.001(4) 0.020(4) -0.008(4) C10 0.058(2) 0.097(4) 0.075(3) 0.004(3) 0.010(2) 0.005(2) C11 0.059(2) 0.097(4) 0.071(3) -0.003(2) 0.013(2) -0.004(2) C12 0.068(3) 0.082(4) 0.102(3) -0.013(3) 0.006(2) 0.002(2) C13 0.064(3) 0.069(3) 0.080(3) -0.010(2) 0.008(2) 0.001(2) C14 0.088(4) 0.088(4) 0.087(3) -0.004(3) 0.017(3) -0.013(3) C15 0.077(4) 0.097(4) 0.136(5) -0.009(4) 0.032(4) -0.020(3) C16 0.059(3) 0.095(4) 0.138(5) -0.026(4) -0.001(3) 0.005(3) C17 0.101(4) 0.109(5) 0.081(3) -0.005(3) -0.010(3) 0.019(4) C18 0.083(3) 0.100(4) 0.089(3) -0.001(3) 0.023(3) -0.001(3) C2A 0.059(8) 0.109(15) 0.091(10) 0.004(10) 0.023(8) 0.004(9) C3A 0.065(9) 0.089(13) 0.099(13) 0.033(11) -0.002(9) -0.006(9) C4A 0.077(12) 0.073(15) 0.078(13) 0.015(10) -0.001(9) -0.012(10) C5A 0.072(12) 0.067(15) 0.103(17) 0.028(12) 0.004(10) 0.007(10) C6A 0.056(11) 0.059(14) 0.082(15) 0.026(11) 0.014(9) 0.006(9) C8A 0.11(3) 0.10(3) 0.10(2) 0.046(19) 0.029(18) -0.06(2) C9A 0.073(14) 0.084(16) 0.073(14) -0.002(12) 0.010(10) -0.005(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O5 1.406(3) . ? S1 O6 1.421(3) . ? S1 N1 1.621(4) . ? S1 C7 1.755(5) . ? O1 C1 1.260(5) . ? O2 C1 1.236(6) . ? O2 H2 0.8400 . ? O3 C10 1.262(5) . ? O4 C10 1.255(6) . ? O4 H4 0.8400 . ? N1 C11 1.432(6) . ? N1 H1 0.838(19) . ? C1 C2A 1.490(17) . ? C1 C2 1.499(8) . ? C2 C3 1.288(9) . ? C2 H7 0.9500 . ? C3 C4 1.468(10) . ? C3 H3 0.9500 . ? C4 C9 1.374(9) . ? C4 C5 1.393(12) . ? C5 C6 1.391(11) . ? C5 H5 0.9500 . ? C6 C7 1.363(13) . ? C6 H6 0.9500 . ? C7 C8 1.328(14) . ? C7 C6A 1.43(2) . ? C7 C8A 1.55(3) . ? C8 C9 1.393(11) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.516(6) . ? C11 C12 1.516(7) . ? C11 H11 1.0000 . ? C12 C13 1.524(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.363(7) . ? C13 C18 1.375(7) . ? C14 C15 1.366(8) . ? C14 H14 0.9500 . ? C15 C16 1.363(9) . ? C15 H15 0.9500 . ? C16 C17 1.349(8) . ? C16 H16 0.9500 . ? C17 C18 1.391(7) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C2A C3A 1.53(2) . ? C2A C3A 1.61(3) 3_575 ? C2A H2A 1.0000 . ? C3A C4A 1.57(3) . ? C3A C2A 1.61(3) 3_575 ? C3A H3A 1.0000 . ? C4A C9A 1.369(15) . ? C4A C5A 1.388(17) . ? C5A C6A 1.397(16) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? C8A C9A 1.398(18) . ? C8A H8A 0.9500 . ? C9A H9A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 S1 O6 120.2(2) . . ? O5 S1 N1 107.7(2) . . ? O6 S1 N1 105.4(2) . . ? O5 S1 C7 108.0(2) . . ? O6 S1 C7 108.3(2) . . ? N1 S1 C7 106.5(2) . . ? C1 O1 H2 48.0 . . ? C1 O2 H2 109.5 . . ? C10 O4 H4 109.5 . . ? C11 N1 S1 121.4(3) . . ? C11 N1 H1 107(3) . . ? S1 N1 H1 118(3) . . ? O2 C1 O1 125.2(4) . . ? O2 C1 C2A 113.5(8) . . ? O1 C1 C2A 108.8(7) . . ? O2 C1 C2 116.6(5) . . ? O1 C1 C2 117.5(5) . . ? C2A C1 C2 46.9(7) . . ? C3 C2 C1 123.2(6) . . ? C3 C2 H7 118.4 . . ? C1 C2 H7 118.4 . . ? C2 C3 C4 127.9(7) . . ? C2 C3 H3 116.1 . . ? C4 C3 H3 116.1 . . ? C9 C4 C5 118.2(8) . . ? C9 C4 C3 118.9(8) . . ? C5 C4 C3 122.9(7) . . ? C6 C5 C4 121.4(8) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C7 C6 C5 116.6(9) . . ? C7 C6 H6 121.7 . . ? C5 C6 H6 121.7 . . ? C8 C7 C6 124.2(7) . . ? C8 C7 S1 119.1(5) . . ? C6 C7 S1 116.7(6) . . ? C6A C7 S1 125.4(9) . . ? C8A C7 S1 122.7(12) . . ? C7 C8 C9 118.8(9) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C4 C9 C8 120.3(9) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? O4 C10 O3 125.5(4) . . ? O4 C10 C11 118.0(4) . . ? O3 C10 C11 116.4(4) . . ? N1 C11 C12 112.0(4) . . ? N1 C11 C10 114.0(4) . . ? C12 C11 C10 106.1(4) . . ? N1 C11 H11 108.2 . . ? C12 C11 H11 108.2 . . ? C10 C11 H11 108.2 . . ? C11 C12 C13 114.8(4) . . ? C11 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.5 . . ? C14 C13 C18 118.5(5) . . ? C14 C13 C12 120.9(5) . . ? C18 C13 C12 120.6(5) . . ? C13 C14 C15 121.6(5) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C16 C15 C14 119.6(5) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C17 C16 C15 120.1(5) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.4(5) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 119.7(5) . . ? C13 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C1 C2A C3A 117.6(15) . . ? C1 C2A H2A 109.3 . . ? C3A C2A H2A 109.3 . . ? C3A C2A H2A 109.3 3_575 . ? C2A C3A C4A 120.2(15) . . ? C4A C3A C2A 115.7(15) . 3_575 ? C2A C3A H3A 109.7 . . ? C4A C3A H3A 109.7 . . ? C2A C3A H3A 109.7 3_575 . ? C9A C4A C5A 119.8(17) . . ? C9A C4A C3A 115.8(17) . . ? C5A C4A C3A 124.3(15) . . ? C4A C5A C6A 120.9(17) . . ? C4A C5A H5A 119.5 . . ? C6A C5A H5A 119.5 . . ? C5A C6A C7 126.4(18) . . ? C5A C6A H6A 116.8 . . ? C7 C6A H6A 116.8 . . ? C9A C8A C7 126(2) . . ? C9A C8A H8A 116.9 . . ? C7 C8A H8A 116.9 . . ? C4A C9A C8A 119(2) . . ? C4A C9A H9A 120.5 . . ? C8A C9A H9A 120.5 . . ? 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 O5 S1 N1 C11 -48.7(4) . . . . ? O6 S1 N1 C11 -178.2(3) . . . . ? C7 S1 N1 C11 66.9(4) . . . . ? H2 O1 C1 O2 -8.9 . . . . ? H2 O1 C1 C2 -179.4 . . . . ? O2 C1 C2 C3 175.1(6) . . . . ? O1 C1 C2 C3 -13.6(10) . . . . ? C2A C1 C2 C3 77.0(11) . . . . ? C1 C2 C3 C4 -174.1(7) . . . . ? C2 C3 C4 C9 -177.7(8) . . . . ? C2 C3 C4 C5 2.0(12) . . . . ? C9 C4 C5 C6 -2.0(13) . . . . ? C3 C4 C5 C6 178.2(8) . . . . ? C4 C5 C6 C7 -4.5(13) . . . . ? C5 C6 C7 C8 7.7(16) . . . . ? C5 C6 C7 S1 -174.0(6) . . . . ? O5 S1 C7 C8 12.1(11) . . . . ? O6 S1 C7 C8 143.8(10) . . . . ? N1 S1 C7 C8 -103.3(10) . . . . ? O5 S1 C7 C6 -166.2(6) . . . . ? O6 S1 C7 C6 -34.5(7) . . . . ? N1 S1 C7 C6 78.4(6) . . . . ? O5 S1 C7 C6A 167.9(13) . . . . ? O6 S1 C7 C6A -60.4(13) . . . . ? N1 S1 C7 C6A 52.5(13) . . . . ? O5 S1 C7 C8A 18(2) . . . . ? O6 S1 C7 C8A 149(2) . . . . ? N1 S1 C7 C8A -98(2) . . . . ? C6 C7 C8 C9 -4(2) . . . . ? C6A C7 C8 C9 19(2) . . . . ? C8A C7 C8 C9 49(23) . . . . ? S1 C7 C8 C9 177.7(11) . . . . ? C5 C4 C9 C8 5.8(16) . . . . ? C3 C4 C9 C8 -174.4(12) . . . . ? C7 C8 C9 C4 -3(2) . . . . ? S1 N1 C11 C12 165.7(3) . . . . ? S1 N1 C11 C10 -73.8(5) . . . . ? O4 C10 C11 N1 -47.0(7) . . . . ? O3 C10 C11 N1 135.6(5) . . . . ? O4 C10 C11 C12 76.7(6) . . . . ? O3 C10 C11 C12 -100.7(6) . . . . ? N1 C11 C12 C13 -68.4(5) . . . . ? C10 C11 C12 C13 166.7(4) . . . . ? C11 C12 C13 C14 107.4(6) . . . . ? C11 C12 C13 C18 -75.6(6) . . . . ? C18 C13 C14 C15 0.5(8) . . . . ? C12 C13 C14 C15 177.5(5) . . . . ? C13 C14 C15 C16 0.2(9) . . . . ? C14 C15 C16 C17 -0.9(10) . . . . ? C15 C16 C17 C18 1.0(10) . . . . ? C14 C13 C18 C17 -0.4(8) . . . . ? C12 C13 C18 C17 -177.4(5) . . . . ? C16 C17 C18 C13 -0.4(9) . . . . ? O2 C1 C2A C3A -176.0(13) . . . . ? O1 C1 C2A C3A 39.7(17) . . . . ? C2 C1 C2A C3A -70.8(15) . . . . ? O2 C1 C2A C3A 76.8(14) . . . 3_575 ? O1 C1 C2A C3A -67.5(15) . . . 3_575 ? C2 C1 C2A C3A -178.0(19) . . . 3_575 ? C1 C2A C3A C4A 115.5(17) . . . . ? C3A C2A C3A C4A -120(2) 3_575 . . . ? C1 C2A C3A C2A -124.2(15) . . . 3_575 ? C3A C2A C3A C2A 0.000(1) 3_575 . . 3_575 ? C2A C3A C4A C9A -171(2) . . . . ? C2A C3A C4A C9A 82(2) 3_575 . . . ? C2A C3A C4A C5A 14(3) . . . . ? C2A C3A C4A C5A -93(3) 3_575 . . . ? C9A C4A C5A C6A -7(4) . . . . ? C3A C4A C5A C6A 168(2) . . . . ? C4A C5A C6A C7 15(4) . . . . ? C8 C7 C6A C5A -9(3) . . . . ? C6 C7 C6A C5A 118(5) . . . . ? C8A C7 C6A C5A -12(3) . . . . ? S1 C7 C6A C5A -166.3(18) . . . . ? C8 C7 C8A C9A -147(28) . . . . ? C6 C7 C8A C9A -17(6) . . . . ? C6A C7 C8A C9A 4(5) . . . . ? S1 C7 C8A C9A 159(3) . . . . ? C5A C4A C9A C8A -1(5) . . . . ? C3A C4A C9A C8A -176(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.841(16) 1.777(15) 2.604(3) 167.1(16) 3_575 O4 H4 O1 0.817(17) 1.924(18) 2.701(3) 158(3) 3_575 N1 H1 O6 0.831(17) 2.19(2) 2.946(4) 152(3) 3_675 _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 67.67 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.325 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.061 data_kaw129b _database_code_depnum_ccdc_archive 'CCDC 895730' #TrackingRef '- wheeler-ChemComm13.CIF' # (rac)-1-II _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O6 S' _chemical_formula_sum 'C18 H17 N O6 S' _chemical_formula_weight 375.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3283(2) _cell_length_b 7.7161(2) _cell_length_c 16.2329(4) _cell_angle_alpha 90.860(1) _cell_angle_beta 97.774(2) _cell_angle_gamma 112.116(2) _cell_volume 840.38(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4638 _cell_measurement_theta_min 2.843 _cell_measurement_theta_max 67.344 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.189 _exptl_crystal_size_mid 0.103 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 2.046 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.679 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_process_details 'SADABS (Bruker, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 101(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 17267 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 67.67 _reflns_number_total 2950 _reflns_number_gt 2671 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2008) and XPREP (Bruker, 2008) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _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. All nonhydrogen atoms were located in a Fourier difference map and refined using ansitropic displacement parameters. NH and OH hydrogen atoms were located in diff maps and refined with N/O-H distances of 0.84(2) angstroms and Uiso = 1.2Ueq of the corresponding O/N atoms. All other H atoms were placed in calculated positions and refined using Ueq = 1.2 x Uiso of the corresponding C atom. The sulfonamide group is disordered over two positions in a 95:5 ratio. The minor component was refined using isotropic displacement parameters. ; _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^)+(0.0582P)^2^+0.4921P] 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 2950 _refine_ls_number_parameters 284 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.002 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 0.78929(5) 0.23431(5) 0.24745(2) 0.02219(9) Uani 1 1 d D . . O1 O 0.72732(17) 1.08163(16) -0.09582(7) 0.0313(3) Uani 1 1 d D . . H4 H 0.721(3) 1.170(2) -0.1236(11) 0.038 Uiso 1 1 d D . . O2 O 0.76770(18) 0.93454(16) -0.20709(7) 0.0327(3) Uani 1 1 d . . . O3 O 1.22122(18) 0.79362(16) 0.30700(7) 0.0329(3) Uani 1 1 d D A . H7 H 1.235(3) 0.880(2) 0.2745(11) 0.039 Uiso 1 1 d D . . O4 O 1.23602(16) 0.62950(15) 0.19500(7) 0.0274(3) Uani 1 1 d . A . O5 O 0.70784(17) 0.27155(17) 0.31776(7) 0.0278(3) Uani 0.9477(15) 1 d P A 1 O6 O 0.7198(2) 0.04919(16) 0.20874(8) 0.0325(3) Uani 0.9477(15) 1 d P A 1 N1 N 1.0266(2) 0.29619(18) 0.27548(8) 0.0225(3) Uani 0.9477(15) 1 d PD A 1 H1 H 1.079(2) 0.237(2) 0.2504(11) 0.027 Uiso 0.9477(15) 1 d PD A 1 C1 C 0.7499(2) 0.9409(2) -0.13360(10) 0.0251(4) Uani 1 1 d . . . C2 C 0.7543(2) 0.7876(2) -0.08128(10) 0.0271(4) Uani 1 1 d . . . H2 H 0.7760 0.6857 -0.1056 0.032 Uiso 1 1 calc R . . C3 C 0.7291(2) 0.7853(2) -0.00158(10) 0.0268(4) Uani 1 1 d . . . H3 H 0.7053 0.8878 0.0209 0.032 Uiso 1 1 calc R . . C4 C 0.7346(2) 0.6407(2) 0.05505(10) 0.0236(3) Uani 1 1 d . . . C5 C 0.7747(2) 0.4841(2) 0.03199(10) 0.0239(3) Uani 1 1 d . A . H5 H 0.7937 0.4651 -0.0237 0.029 Uiso 1 1 calc R . . C6 C 0.7868(2) 0.3575(2) 0.08945(10) 0.0228(3) Uani 1 1 d . . . H6 H 0.8152 0.2523 0.0737 0.027 Uiso 1 1 calc R A . C7 C 0.7572(2) 0.3852(2) 0.17067(9) 0.0208(3) Uani 1 1 d . A . C8 C 0.7114(2) 0.5356(2) 0.19404(10) 0.0243(3) Uani 1 1 d . . . H8 H 0.6882 0.5518 0.2493 0.029 Uiso 1 1 calc R A . C9 C 0.6998(2) 0.6624(2) 0.13591(10) 0.0271(4) Uani 1 1 d . A . H9 H 0.6677 0.7654 0.1516 0.033 Uiso 1 1 calc R . . C10 C 1.2059(2) 0.6397(2) 0.26646(9) 0.0221(3) Uani 1 1 d D . . C11 C 1.1453(2) 0.4739(2) 0.32195(10) 0.0215(4) Uani 0.9477(15) 1 d PD A 1 H11 H 1.0631 0.4985 0.3616 0.026 Uiso 0.9477(15) 1 calc PR A 1 C12 C 1.3336(2) 0.4659(2) 0.37376(10) 0.0272(4) Uani 1 1 d D . . H12A H 1.4062 0.4210 0.3369 0.033 Uiso 1 1 calc R A 1 H12B H 1.4223 0.5939 0.3971 0.033 Uiso 1 1 calc R A 1 C13 C 1.2855(2) 0.3381(2) 0.44414(9) 0.0219(3) Uani 1 1 d . A . C14 C 1.3320(2) 0.1788(2) 0.44568(10) 0.0265(4) Uani 1 1 d . . . H14 H 1.3918 0.1492 0.4020 0.032 Uiso 1 1 calc R A . C15 C 1.2906(2) 0.0628(2) 0.51150(12) 0.0314(4) Uani 1 1 d . A . H15 H 1.3234 -0.0452 0.5126 0.038 Uiso 1 1 calc R . . C16 C 1.2024(2) 0.1038(2) 0.57501(11) 0.0310(4) Uani 1 1 d . . . H16 H 1.1730 0.0237 0.6194 0.037 Uiso 1 1 calc R A . C17 C 1.1574(2) 0.2620(2) 0.57357(10) 0.0278(4) Uani 1 1 d . A . H17 H 1.0969 0.2909 0.6172 0.033 Uiso 1 1 calc R . . C18 C 1.1997(2) 0.3789(2) 0.50916(10) 0.0233(3) Uani 1 1 d . . . H18 H 1.1698 0.4884 0.5094 0.028 Uiso 1 1 calc R A . O5A O 0.610(4) 0.163(3) 0.2824(14) 0.033(6) Uani 0.0523(15) 1 d P A 2 O6A O 0.849(3) 0.099(3) 0.2025(14) 0.028(5) Uani 0.0523(15) 1 d P A 2 N1A N 0.955(2) 0.365(3) 0.3165(11) 0.0175(11) Uani 0.0523(15) 1 d PDU A 2 H1A H 0.930(7) 0.376(9) 0.3649(16) 0.021 Uiso 0.0523(15) 1 d PD A 2 C11A C 1.161(2) 0.451(3) 0.3054(15) 0.0362(11) Uani 0.0523(15) 1 d PDU A 2 H11A H 1.1722 0.3679 0.2602 0.043 Uiso 0.0523(15) 1 calc PR A 2 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 0.02554(17) 0.01883(16) 0.02041(18) 0.00478(13) 0.00093(14) 0.00721(14) O1 0.0445(6) 0.0309(6) 0.0224(6) 0.0094(4) 0.0078(5) 0.0177(5) O2 0.0492(6) 0.0280(5) 0.0270(6) 0.0079(5) 0.0101(5) 0.0197(5) O3 0.0534(6) 0.0238(5) 0.0273(6) 0.0091(4) 0.0151(5) 0.0180(5) O4 0.0364(5) 0.0262(5) 0.0211(5) 0.0047(4) 0.0054(4) 0.0133(4) O5 0.0269(6) 0.0334(6) 0.0234(6) 0.0090(5) 0.0065(5) 0.0107(5) O6 0.0397(7) 0.0208(5) 0.0322(7) 0.0026(5) -0.0038(6) 0.0092(5) N1 0.0278(6) 0.0201(6) 0.0209(7) 0.0010(5) 0.0010(5) 0.0114(5) C1 0.0231(7) 0.0224(7) 0.0286(8) 0.0029(6) 0.0019(6) 0.0080(6) C2 0.0285(7) 0.0256(7) 0.0279(8) 0.0043(6) 0.0040(6) 0.0113(6) C3 0.0257(7) 0.0242(7) 0.0290(8) 0.0029(6) 0.0016(6) 0.0086(6) C4 0.0193(7) 0.0234(7) 0.0248(8) 0.0037(6) -0.0012(6) 0.0060(6) C5 0.0209(7) 0.0303(8) 0.0190(7) 0.0035(6) 0.0026(6) 0.0080(6) C6 0.0229(7) 0.0231(7) 0.0225(7) 0.0014(6) 0.0012(6) 0.0096(6) C7 0.0185(6) 0.0215(7) 0.0200(7) 0.0032(6) -0.0010(5) 0.0060(5) C8 0.0282(7) 0.0247(7) 0.0202(7) 0.0017(6) 0.0024(6) 0.0107(6) C9 0.0329(8) 0.0228(7) 0.0276(8) 0.0030(6) 0.0035(6) 0.0132(6) C10 0.0221(7) 0.0225(7) 0.0215(7) 0.0034(6) 0.0012(6) 0.0088(6) C11 0.0256(7) 0.0208(7) 0.0177(8) 0.0033(6) 0.0025(6) 0.0088(6) C12 0.0259(7) 0.0303(8) 0.0240(8) 0.0086(6) 0.0028(6) 0.0090(6) C13 0.0194(7) 0.0229(7) 0.0185(7) 0.0028(6) -0.0013(6) 0.0040(6) C14 0.0211(7) 0.0276(8) 0.0293(8) -0.0024(6) 0.0028(6) 0.0081(6) C15 0.0268(7) 0.0203(7) 0.0463(10) 0.0066(7) -0.0005(7) 0.0101(6) C16 0.0212(7) 0.0333(8) 0.0301(9) 0.0135(7) -0.0018(6) 0.0025(7) C17 0.0218(7) 0.0375(8) 0.0206(8) 0.0019(6) 0.0021(6) 0.0078(6) C18 0.0205(7) 0.0236(7) 0.0248(8) 0.0006(6) -0.0018(6) 0.0092(6) O5A 0.045(13) 0.022(10) 0.024(11) 0.012(9) 0.004(10) 0.006(10) O6A 0.009(8) 0.046(12) 0.034(11) 0.019(9) 0.011(8) 0.012(8) N1A 0.0176(12) 0.0175(13) 0.0175(13) 0.0013(9) 0.0025(8) 0.0068(8) C11A 0.0361(13) 0.0363(13) 0.0363(14) 0.0026(9) 0.0057(8) 0.0139(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 O5A 1.42(2) . ? S1 O6 1.4260(12) . ? S1 O5 1.4300(13) . ? S1 O6A 1.49(2) . ? S1 N1A 1.559(17) . ? S1 N1 1.6167(14) . ? S1 C7 1.7706(15) . ? O1 C1 1.314(2) . ? O1 H4 0.837(14) . ? O2 C1 1.220(2) . ? O3 C10 1.3082(19) . ? O3 H7 0.842(14) . ? O4 C10 1.2168(19) . ? N1 C11 1.4489(19) . ? N1 H1 0.831(14) . ? C1 C2 1.473(2) . ? C2 C3 1.331(2) . ? C2 H2 0.9500 . ? C3 C4 1.465(2) . ? C3 H3 0.9500 . ? C4 C9 1.390(2) . ? C4 C5 1.404(2) . ? C5 C6 1.379(2) . ? C5 H5 0.9500 . ? C6 C7 1.391(2) . ? C6 H6 0.9500 . ? C7 C8 1.385(2) . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11A 1.535(16) . ? C10 C11 1.537(2) . ? C11 C12 1.539(2) . ? C11 H11 1.0000 . ? C12 C13 1.511(2) . ? C12 C11A 1.534(16) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.388(2) . ? C13 C14 1.393(2) . ? C14 C15 1.395(2) . ? C14 H14 0.9500 . ? C15 C16 1.380(3) . ? C15 H15 0.9500 . ? C16 C17 1.379(3) . ? C16 H16 0.9500 . ? C17 C18 1.381(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? N1A H1A 0.840(19) . ? C11A H11A 1.0000 . ? 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 O6 S1 O5 120.49(8) . . ? O5A S1 O6A 118.2(12) . . ? O5A S1 N1A 107.3(11) . . ? O6A S1 N1A 114.0(11) . . ? O5A S1 N1 139.4(9) . . ? O6 S1 N1 105.94(8) . . ? O5 S1 N1 107.73(7) . . ? O6A S1 N1 73.3(8) . . ? O5A S1 C7 107.1(9) . . ? O6 S1 C7 108.12(7) . . ? O5 S1 C7 106.98(8) . . ? O6A S1 C7 104.2(8) . . ? N1A S1 C7 105.0(8) . . ? N1 S1 C7 106.89(7) . . ? C1 O1 H4 118.8(14) . . ? C10 O3 H7 110.5(13) . . ? C11 N1 S1 121.13(12) . . ? C11 N1 H1 121.1(11) . . ? S1 N1 H1 115.4(11) . . ? O2 C1 O1 123.31(15) . . ? O2 C1 C2 120.92(15) . . ? O1 C1 C2 115.77(14) . . ? C3 C2 C1 123.13(16) . . ? C3 C2 H2 118.4 . . ? C1 C2 H2 118.4 . . ? C2 C3 C4 126.63(16) . . ? C2 C3 H3 116.7 . . ? C4 C3 H3 116.7 . . ? C9 C4 C5 118.92(15) . . ? C9 C4 C3 117.63(15) . . ? C5 C4 C3 123.45(15) . . ? C6 C5 C4 120.57(15) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.40(15) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 120.94(14) . . ? C8 C7 S1 118.70(12) . . ? C6 C7 S1 120.28(12) . . ? C7 C8 C9 119.27(15) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C4 120.83(16) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? O4 C10 O3 124.80(14) . . ? O4 C10 C11A 111.2(11) . . ? O3 C10 C11A 123.9(11) . . ? O4 C10 C11 124.78(14) . . ? O3 C10 C11 110.43(13) . . ? N1 C11 C10 113.22(13) . . ? N1 C11 C12 111.09(13) . . ? C10 C11 C12 109.20(12) . . ? N1 C11 H11 107.7 . . ? C10 C11 H11 107.7 . . ? C12 C11 H11 107.7 . . ? C13 C12 C11A 117.3(7) . . ? C13 C12 C11 112.22(13) . . ? C11A C12 C11 13.9(11) . . ? C13 C12 H12A 109.2 . . ? C11A C12 H12A 95.4 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11A C12 H12B 116.6 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C18 C13 C14 118.85(14) . . ? C18 C13 C12 121.09(15) . . ? C14 C13 C12 120.04(15) . . ? C13 C14 C15 119.91(16) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.51(16) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 119.48(16) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.48(16) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C13 120.76(15) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? C11A N1A S1 122.9(15) . . ? C11A N1A H1A 116(4) . . ? S1 N1A H1A 120(3) . . ? N1A C11A C12 122.9(16) . . ? N1A C11A C10 111.7(15) . . ? C12 C11A C10 109.5(10) . . ? N1A C11A H11A 103.4 . . ? C12 C11A H11A 103.4 . . ? C10 C11A H11A 103.4 . . ? 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 O5A S1 N1 C11 -76.9(14) . . . . ? O6 S1 N1 C11 -176.08(12) . . . . ? O5 S1 N1 C11 -45.89(14) . . . . ? O6A S1 N1 C11 169.0(9) . . . . ? N1A S1 N1 C11 -25.0(11) . . . . ? C7 S1 N1 C11 68.78(13) . . . . ? O2 C1 C2 C3 -177.78(15) . . . . ? O1 C1 C2 C3 2.6(2) . . . . ? C1 C2 C3 C4 -178.89(14) . . . . ? C2 C3 C4 C9 -178.48(15) . . . . ? C2 C3 C4 C5 2.2(2) . . . . ? C9 C4 C5 C6 -2.4(2) . . . . ? C3 C4 C5 C6 176.96(14) . . . . ? C4 C5 C6 C7 0.5(2) . . . . ? C5 C6 C7 C8 1.4(2) . . . . ? C5 C6 C7 S1 -175.50(11) . . . . ? O5A S1 C7 C8 57.6(10) . . . . ? O6 S1 C7 C8 146.45(12) . . . . ? O5 S1 C7 C8 15.30(13) . . . . ? O6A S1 C7 C8 -176.4(8) . . . . ? N1A S1 C7 C8 -56.3(7) . . . . ? N1 S1 C7 C8 -99.89(13) . . . . ? O5A S1 C7 C6 -125.4(10) . . . . ? O6 S1 C7 C6 -36.54(14) . . . . ? O5 S1 C7 C6 -167.70(11) . . . . ? O6A S1 C7 C6 0.6(8) . . . . ? N1A S1 C7 C6 120.7(7) . . . . ? N1 S1 C7 C6 77.12(13) . . . . ? C6 C7 C8 C9 -1.5(2) . . . . ? S1 C7 C8 C9 175.46(11) . . . . ? C7 C8 C9 C4 -0.4(2) . . . . ? C5 C4 C9 C8 2.3(2) . . . . ? C3 C4 C9 C8 -177.09(14) . . . . ? S1 N1 C11 C10 -82.09(16) . . . . ? S1 N1 C11 C12 154.60(11) . . . . ? O4 C10 C11 N1 -31.3(2) . . . . ? O3 C10 C11 N1 148.96(14) . . . . ? C11A C10 C11 N1 -45(2) . . . . ? O4 C10 C11 C12 93.04(18) . . . . ? O3 C10 C11 C12 -86.70(16) . . . . ? C11A C10 C11 C12 79(2) . . . . ? N1 C11 C12 C13 -68.23(18) . . . . ? C10 C11 C12 C13 166.19(13) . . . . ? N1 C11 C12 C11A 46(2) . . . . ? C10 C11 C12 C11A -80(2) . . . . ? C11A C12 C13 C18 -79.0(12) . . . . ? C11 C12 C13 C18 -64.74(18) . . . . ? C11A C12 C13 C14 102.7(12) . . . . ? C11 C12 C13 C14 116.99(16) . . . . ? C18 C13 C14 C15 0.5(2) . . . . ? C12 C13 C14 C15 178.85(14) . . . . ? C13 C14 C15 C16 0.5(2) . . . . ? C14 C15 C16 C17 -0.8(2) . . . . ? C15 C16 C17 C18 0.1(2) . . . . ? C16 C17 C18 C13 1.0(2) . . . . ? C14 C13 C18 C17 -1.3(2) . . . . ? C12 C13 C18 C17 -179.54(14) . . . . ? O5A S1 N1A C11A 175.0(18) . . . . ? O6 S1 N1A C11A 74(2) . . . . ? O5 S1 N1A C11A -174(2) . . . . ? O6A S1 N1A C11A 42(2) . . . . ? N1 S1 N1A C11A 27.5(12) . . . . ? C7 S1 N1A C11A -71.3(19) . . . . ? S1 N1A C11A C12 -138.9(18) . . . . ? S1 N1A C11A C10 88(2) . . . . ? C13 C12 C11A N1A 18(3) . . . . ? C11 C12 C11A N1A -54(3) . . . . ? C13 C12 C11A C10 152.4(10) . . . . ? C11 C12 C11A C10 81(3) . . . . ? O4 C10 C11A N1A -109.2(18) . . . . ? O3 C10 C11A N1A 74.6(17) . . . . ? C11 C10 C11A N1A 59(2) . . . . ? O4 C10 C11A C12 111.2(15) . . . . ? O3 C10 C11A C12 -65.1(17) . . . . ? C11 C10 C11A C12 -81(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H4 O4 0.837(14) 1.902(15) 2.7214(16) 166(2) 2_775 O3 H7 O2 0.842(14) 1.818(15) 2.6545(16) 172(2) 2_775 N1 H1 O2 0.831(14) 2.194(15) 3.0148(19) 169.3(18) 2_765 C9 H9 O6 0.95 2.24 3.137(2) 157.3 1_565 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 67.67 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.306 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.057 data_kaw67 _database_code_depnum_ccdc_archive 'CCDC 895731' #TrackingRef '- wheeler-ChemComm13.CIF' # (R)-1, unreacted _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O6 S' _chemical_formula_sum 'C18 H17 N O6 S' _chemical_formula_weight 375.39 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.2820(5) _cell_length_b 14.1275(6) _cell_length_c 11.8374(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.725(2) _cell_angle_gamma 90.00 _cell_volume 1707.66(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2327 _cell_measurement_theta_min 5.345 _cell_measurement_theta_max 60.793 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 2.014 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.697 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'SADABS (Bruker, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 22936 _diffrn_reflns_av_R_equivalents 0.0808 _diffrn_reflns_av_sigmaI/netI 0.1160 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 67.46 _reflns_number_total 5821 _reflns_number_gt 2989 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2008) and XPREP (Bruker, 2008) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _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. All non-hydrogen atoms were located in a single difference Fourier map and refined with anisotropic thermal parameters. The N-H and O-H hydrogen atoms were located in difference density Fourier maps and refined O/N-H stisatnce of 0.84(2) angstroms and Uiso = 1.2Ueq of the corresponding O/N atoms. All other H atoms were place in calculated positions and refined with Uiso = 1.2Ueq of the corresponding C atom (Uiso = 1.5eq for methyl C-H groups). ; _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^)+(0.0260P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_number_reflns 5821 _refine_ls_number_parameters 488 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.1690 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 S1A S 0.1704(2) 0.30316(13) 0.40236(16) 0.0399(5) Uani 1 1 d . . . O1A O 1.0088(5) 0.3457(4) 0.7232(4) 0.0588(16) Uani 1 1 d D . . H1A H 1.0799(19) 0.325(4) 0.758(5) 0.071 Uiso 1 1 d D . . O2A O 0.9255(5) 0.2497(4) 0.8487(4) 0.0590(16) Uani 1 1 d D . . O3A O 0.1870(5) 0.2733(3) 0.2892(4) 0.0480(14) Uani 1 1 d . . . O4A O 0.0668(5) 0.2639(3) 0.4583(4) 0.0475(14) Uani 1 1 d . . . O5A O 0.3523(4) 0.5123(4) 0.5416(4) 0.0488(14) Uani 1 1 d D . . O6A O 0.2327(5) 0.4754(4) 0.6833(4) 0.0479(14) Uani 1 1 d D . . H6A H 0.301(3) 0.492(5) 0.7218(16) 0.058 Uiso 1 1 d D . . N1A N 0.1474(5) 0.4160(4) 0.3942(5) 0.0356(14) Uani 1 1 d D . . H13 H 0.196(5) 0.451(4) 0.359(4) 0.043 Uiso 1 1 d D . . C1A C 0.9145(9) 0.2942(6) 0.7589(7) 0.049(2) Uani 1 1 d . . . C2A C 0.7923(8) 0.2985(6) 0.6806(6) 0.048(2) Uani 1 1 d . . . H2A H 0.7944 0.3302 0.6101 0.058 Uiso 1 1 calc R . . C3A C 0.6804(7) 0.2612(5) 0.7020(6) 0.0407(19) Uani 1 1 d . . . H3A H 0.6798 0.2268 0.7709 0.049 Uiso 1 1 calc R . . C4A C 0.5555(7) 0.2690(6) 0.6266(6) 0.0353(19) Uani 1 1 d . . . C5A C 0.5508(8) 0.3052(6) 0.5187(6) 0.053(2) Uani 1 1 d . . . H5A H 0.6299 0.3249 0.4915 0.063 Uiso 1 1 calc R . . C6A C 0.4345(8) 0.3139(6) 0.4486(6) 0.046(2) Uani 1 1 d . . . H1 H 0.4332 0.3388 0.3739 0.055 Uiso 1 1 calc R . . C7A C 0.3197(7) 0.2857(5) 0.4894(6) 0.0322(19) Uani 1 1 d . . . C8A C 0.3190(7) 0.2503(5) 0.5979(6) 0.042(2) Uani 1 1 d . . . H8A H 0.2394 0.2327 0.6257 0.051 Uiso 1 1 calc R . . C9A C 0.4405(7) 0.2410(6) 0.6664(6) 0.044(2) Uani 1 1 d . . . H9A H 0.4430 0.2151 0.7407 0.052 Uiso 1 1 calc R . . C10A C 0.2492(7) 0.4872(5) 0.5760(5) 0.039(2) Uani 1 1 d . . . C11A C 0.1236(7) 0.4688(5) 0.4973(5) 0.0380(19) Uani 1 1 d . . . H11A H 0.0632 0.4308 0.5397 0.046 Uiso 1 1 calc R . . C12A C 0.0585(8) 0.5642(5) 0.4656(6) 0.042(2) Uani 1 1 d . . . H12A H 0.0527 0.6017 0.5355 0.050 Uiso 1 1 calc R . . H12B H 0.1126 0.6000 0.4166 0.050 Uiso 1 1 calc R . . C13A C -0.0770(9) 0.5501(6) 0.4038(7) 0.046(2) Uani 1 1 d . . . C14A C -0.1029(9) 0.5660(6) 0.2866(6) 0.052(2) Uani 1 1 d . . . H14A H -0.0354 0.5869 0.2442 0.063 Uiso 1 1 calc R . . C15A C -0.2308(10) 0.5504(6) 0.2323(7) 0.071(3) Uani 1 1 d . . . H15A H -0.2490 0.5598 0.1526 0.086 Uiso 1 1 calc R . . C16A C -0.3283(9) 0.5220(7) 0.2931(9) 0.070(3) Uani 1 1 d . . . H16A H -0.4137 0.5109 0.2554 0.084 Uiso 1 1 calc R . . C17A C -0.3038(8) 0.5094(7) 0.4079(8) 0.067(2) Uani 1 1 d . . . H17A H -0.3727 0.4910 0.4502 0.080 Uiso 1 1 calc R . . C18A C -0.1793(8) 0.5233(6) 0.4628(6) 0.048(2) Uani 1 1 d . . . H18A H -0.1636 0.5143 0.5428 0.058 Uiso 1 1 calc R . . S1B S 1.32849(18) 0.50666(13) 1.10582(14) 0.0358(5) Uani 1 1 d . . . O1B O 0.4609(5) 0.4786(4) 0.8151(4) 0.0477(14) Uani 1 1 d D . . O2B O 0.5778(5) 0.5278(4) 0.6770(4) 0.0490(15) Uani 1 1 d D . . H2B H 0.505(2) 0.526(5) 0.638(2) 0.059 Uiso 1 1 d D . . O3B O 1.4038(4) 0.5889(3) 1.0860(4) 0.0414(13) Uani 1 1 d . . . O4B O 1.3141(4) 0.4785(3) 1.2189(3) 0.0411(13) Uani 1 1 d . . . O5B O 1.2207(5) 0.3445(4) 0.8692(4) 0.0496(15) Uani 1 1 d D . . O6B O 1.1410(5) 0.2501(4) 0.9944(4) 0.0521(14) Uani 1 1 d D . . H6B H 1.079(4) 0.243(4) 0.942(3) 0.063 Uiso 1 1 d D . . N1B N 1.3986(5) 0.4192(4) 1.0446(5) 0.0418(15) Uani 1 1 d D . . H2 H 1.427(6) 0.432(4) 0.983(3) 0.050 Uiso 1 1 d D . . C1B C 0.5649(7) 0.5030(6) 0.7813(6) 0.0417(19) Uani 1 1 d . . . C2B C 0.6870(7) 0.5034(5) 0.8589(5) 0.0382(18) Uani 1 1 d . . . H3 H 0.6841 0.4801 0.9338 0.046 Uiso 1 1 calc R . . C3B C 0.8002(7) 0.5337(6) 0.8321(6) 0.045(2) Uani 1 1 d . . . H3B H 0.8002 0.5608 0.7587 0.054 Uiso 1 1 calc R . . C4B C 0.9263(7) 0.5303(6) 0.9036(6) 0.039(2) Uani 1 1 d . . . C5B C 0.9430(8) 0.4799(6) 1.0047(6) 0.048(2) Uani 1 1 d . . . H5B H 0.8702 0.4481 1.0299 0.057 Uiso 1 1 calc R . . C6B C 1.0643(8) 0.4751(6) 1.0698(6) 0.049(2) Uani 1 1 d . . . H4 H 1.0749 0.4406 1.1392 0.058 Uiso 1 1 calc R . . C7B C 1.1683(7) 0.5211(5) 1.0320(5) 0.0368(19) Uani 1 1 d . . . C8B C 1.1554(7) 0.5708(5) 0.9326(6) 0.041(2) Uani 1 1 d . . . H8B H 1.2292 0.6010 0.9070 0.049 Uiso 1 1 calc R . . C9B C 1.0331(8) 0.5765(5) 0.8690(6) 0.045(2) Uani 1 1 d . . . H9B H 1.0229 0.6128 0.8009 0.054 Uiso 1 1 calc R . . C10B C 1.2281(7) 0.3070(5) 0.9622(6) 0.0394(19) Uani 1 1 d . . . C11B C 1.3489(6) 0.3234(5) 1.0498(6) 0.040(2) Uani 1 1 d . . . H11B H 1.3254 0.3106 1.1279 0.048 Uiso 1 1 calc R . . C12B C 1.4528(7) 0.2540(6) 1.0226(6) 0.045(2) Uani 1 1 d . . . H12C H 1.4780 0.2687 0.9464 0.054 Uiso 1 1 calc R . . H12D H 1.4153 0.1893 1.0196 0.054 Uiso 1 1 calc R . . C13B C 1.5750(8) 0.2554(6) 1.1087(7) 0.041(2) Uani 1 1 d . . . C14B C 1.5691(9) 0.2214(6) 1.2144(7) 0.053(2) Uani 1 1 d . . . H14B H 1.4881 0.1983 1.2344 0.064 Uiso 1 1 calc R . . C15B C 1.6813(9) 0.2195(6) 1.2963(7) 0.064(3) Uani 1 1 d . . . H15B H 1.6773 0.1927 1.3694 0.077 Uiso 1 1 calc R . . C16B C 1.7942(9) 0.2567(6) 1.2679(8) 0.067(3) Uani 1 1 d . . . H16B H 1.8689 0.2582 1.3232 0.080 Uiso 1 1 calc R . . C17B C 1.8037(10) 0.2920(6) 1.1630(9) 0.073(3) Uani 1 1 d . . . H17B H 1.8844 0.3164 1.1439 0.088 Uiso 1 1 calc R . . C18B C 1.6898(8) 0.2918(6) 1.0816(7) 0.059(3) Uani 1 1 d . . . H18B H 1.6942 0.3172 1.0079 0.071 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 S1A 0.0373(13) 0.0397(13) 0.0404(11) 0.0004(10) -0.0052(9) -0.0036(11) O1A 0.041(4) 0.092(5) 0.042(3) -0.003(3) -0.002(3) -0.017(3) O2A 0.052(4) 0.069(4) 0.052(3) 0.016(3) -0.013(3) -0.006(3) O3A 0.060(4) 0.044(3) 0.038(3) -0.005(2) -0.006(3) 0.000(3) O4A 0.035(3) 0.044(3) 0.060(3) 0.013(3) -0.007(3) -0.014(3) O5A 0.030(3) 0.070(4) 0.047(3) -0.005(3) 0.009(2) -0.010(3) O6A 0.043(3) 0.069(4) 0.031(3) -0.004(3) -0.001(2) -0.009(3) N1A 0.027(4) 0.045(4) 0.035(3) 0.010(3) 0.004(3) -0.011(3) C1A 0.040(5) 0.054(6) 0.050(5) -0.018(5) -0.002(4) 0.002(5) C2A 0.045(5) 0.058(6) 0.041(4) 0.006(4) -0.002(4) 0.001(5) C3A 0.040(5) 0.040(5) 0.042(5) 0.000(4) 0.003(4) 0.001(4) C4A 0.033(5) 0.039(5) 0.033(4) -0.001(4) -0.004(3) -0.001(4) C5A 0.030(5) 0.080(6) 0.047(5) 0.007(5) 0.000(4) -0.001(5) C6A 0.039(5) 0.059(6) 0.042(4) 0.008(4) 0.013(4) -0.010(5) C7A 0.035(5) 0.031(5) 0.029(4) 0.002(4) -0.005(3) 0.004(3) C8A 0.032(5) 0.045(5) 0.048(5) 0.007(4) 0.002(4) -0.009(4) C9A 0.042(5) 0.054(5) 0.036(4) 0.004(4) 0.006(4) -0.004(4) C10A 0.039(5) 0.045(5) 0.029(4) -0.001(4) -0.005(4) 0.004(4) C11A 0.037(5) 0.047(5) 0.030(4) 0.007(4) 0.004(3) 0.000(4) C12A 0.046(5) 0.040(5) 0.039(4) 0.002(4) 0.005(4) 0.000(4) C13A 0.044(6) 0.038(6) 0.058(5) -0.016(4) 0.009(5) 0.005(4) C14A 0.061(6) 0.053(6) 0.041(5) -0.010(4) -0.003(4) 0.011(5) C15A 0.092(9) 0.079(8) 0.037(5) -0.021(5) -0.017(6) 0.046(7) C16A 0.046(6) 0.065(7) 0.093(7) -0.037(7) -0.014(6) 0.019(6) C17A 0.044(5) 0.061(6) 0.094(7) -0.015(6) 0.004(5) -0.002(5) C18A 0.042(5) 0.051(6) 0.049(4) 0.013(4) -0.001(4) 0.008(4) S1B 0.0288(11) 0.0461(13) 0.0313(9) 0.0014(10) -0.0012(8) -0.0025(11) O1B 0.034(3) 0.070(4) 0.038(3) 0.003(3) 0.000(2) -0.004(3) O2B 0.032(3) 0.076(4) 0.038(3) 0.002(3) -0.001(2) -0.009(3) O3B 0.035(3) 0.047(3) 0.041(3) 0.008(2) -0.002(2) -0.003(3) O4B 0.033(3) 0.061(4) 0.028(3) 0.009(2) -0.002(2) -0.008(3) O5B 0.046(4) 0.072(4) 0.028(3) 0.006(3) -0.009(2) -0.003(3) O6B 0.045(3) 0.053(4) 0.054(3) 0.003(3) -0.013(3) -0.012(3) N1B 0.035(4) 0.055(4) 0.036(4) 0.009(3) 0.003(3) -0.005(3) C1B 0.033(5) 0.046(5) 0.046(4) 0.006(4) 0.002(4) 0.002(4) C2B 0.042(5) 0.039(5) 0.033(4) 0.001(4) 0.003(3) -0.002(4) C3B 0.029(4) 0.070(6) 0.038(4) 0.000(4) 0.008(4) -0.001(4) C4B 0.032(5) 0.044(5) 0.039(4) -0.001(4) -0.002(4) -0.002(4) C5B 0.036(5) 0.059(6) 0.049(5) 0.002(4) 0.005(4) -0.005(4) C6B 0.038(5) 0.066(6) 0.042(5) 0.009(4) 0.003(4) -0.005(4) C7B 0.040(5) 0.041(5) 0.030(4) -0.004(4) 0.002(3) -0.008(4) C8B 0.021(4) 0.056(6) 0.047(4) 0.002(4) 0.006(4) -0.009(4) C9B 0.043(5) 0.051(5) 0.040(4) 0.004(4) 0.001(4) -0.004(4) C10B 0.040(5) 0.035(5) 0.043(5) 0.000(4) 0.005(4) -0.002(4) C11B 0.024(4) 0.057(6) 0.040(4) 0.002(4) 0.002(3) -0.010(4) C12B 0.037(5) 0.044(5) 0.051(5) -0.010(4) -0.006(4) 0.003(4) C13B 0.033(5) 0.034(5) 0.053(5) -0.001(4) -0.004(4) 0.006(4) C14B 0.051(6) 0.051(6) 0.056(5) -0.006(4) 0.001(5) 0.008(4) C15B 0.079(7) 0.052(6) 0.058(6) -0.006(5) -0.006(6) 0.011(5) C16B 0.061(7) 0.046(6) 0.084(7) 0.000(5) -0.028(6) 0.011(6) C17B 0.057(7) 0.043(6) 0.118(9) 0.018(6) 0.004(6) -0.009(5) C18B 0.051(6) 0.062(6) 0.061(5) 0.012(5) -0.008(5) -0.003(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 S1A O4A 1.431(5) . ? S1A O3A 1.433(5) . ? S1A N1A 1.612(6) . ? S1A C7A 1.763(7) . ? O1A C1A 1.321(9) . ? O1A H1A 0.85(2) . ? O2A C1A 1.229(9) . ? O5A C10A 1.232(8) . ? O6A C10A 1.311(7) . ? O6A H6A 0.82(2) . ? N1A C11A 1.476(8) . ? N1A H13 0.839(10) . ? C1A C2A 1.472(11) . ? C2A C3A 1.317(10) . ? C2A H2A 0.9500 . ? C3A C4A 1.479(10) . ? C3A H3A 0.9500 . ? C4A C5A 1.372(10) . ? C4A C9A 1.381(9) . ? C5A C6A 1.379(10) . ? C5A H5A 0.9500 . ? C6A C7A 1.385(10) . ? C6A H1 0.9500 . ? C7A C8A 1.380(9) . ? C8A C9A 1.413(9) . ? C8A H8A 0.9500 . ? C9A H9A 0.9500 . ? C10A C11A 1.523(9) . ? C11A C12A 1.532(9) . ? C11A H11A 1.0000 . ? C12A C13A 1.509(11) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A C18A 1.382(10) . ? C13A C14A 1.400(10) . ? C14A C15A 1.412(12) . ? C14A H14A 0.9500 . ? C15A C16A 1.361(11) . ? C15A H15A 0.9500 . ? C16A C17A 1.365(11) . ? C16A H16A 0.9500 . ? C17A C18A 1.381(10) . ? C17A H17A 0.9500 . ? C18A H18A 0.9500 . ? S1B O4B 1.420(4) . ? S1B O3B 1.431(5) . ? S1B N1B 1.642(6) . ? S1B C7B 1.783(8) . ? O1B C1B 1.234(8) . ? O2B C1B 1.306(7) . ? O2B H2B 0.83(2) . ? O5B C10B 1.216(8) . ? O6B C10B 1.294(8) . ? O6B H6B 0.84(2) . ? N1B C11B 1.451(9) . ? N1B H2 0.842(10) . ? C1B C2B 1.466(9) . ? C2B C3B 1.313(9) . ? C2B H3 0.9500 . ? C3B C4B 1.463(10) . ? C3B H3B 0.9500 . ? C4B C9B 1.381(9) . ? C4B C5B 1.387(9) . ? C5B C6B 1.389(11) . ? C5B H5B 0.9500 . ? C6B C7B 1.371(9) . ? C6B H4 0.9500 . ? C7B C8B 1.363(9) . ? C8B C9B 1.391(10) . ? C8B H8B 0.9500 . ? C9B H9B 0.9500 . ? C10B C11B 1.539(10) . ? C11B C12B 1.512(9) . ? C11B H11B 1.0000 . ? C12B C13B 1.523(10) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B C14B 1.348(10) . ? C13B C18B 1.359(11) . ? C14B C15B 1.418(11) . ? C14B H14B 0.9500 . ? C15B C16B 1.352(11) . ? C15B H15B 0.9500 . ? C16B C17B 1.353(11) . ? C16B H16B 0.9500 . ? C17B C18B 1.426(12) . ? C17B H17B 0.9500 . ? C18B H18B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4A S1A O3A 119.6(3) . . ? O4A S1A N1A 107.4(3) . . ? O3A S1A N1A 105.5(3) . . ? O4A S1A C7A 108.7(3) . . ? O3A S1A C7A 108.3(3) . . ? N1A S1A C7A 106.6(3) . . ? C1A O1A H1A 106.4(19) . . ? C10A O6A H6A 107.6(16) . . ? C11A N1A S1A 119.2(4) . . ? C11A N1A H13 106(4) . . ? S1A N1A H13 121(4) . . ? O2A C1A O1A 124.2(8) . . ? O2A C1A C2A 123.4(8) . . ? O1A C1A C2A 112.4(8) . . ? C3A C2A C1A 124.3(8) . . ? C3A C2A H2A 117.9 . . ? C1A C2A H2A 117.9 . . ? C2A C3A C4A 124.8(7) . . ? C2A C3A H3A 117.6 . . ? C4A C3A H3A 117.6 . . ? C5A C4A C9A 119.1(7) . . ? C5A C4A C3A 121.5(7) . . ? C9A C4A C3A 119.4(7) . . ? C4A C5A C6A 121.8(8) . . ? C4A C5A H5A 119.1 . . ? C6A C5A H5A 119.1 . . ? C5A C6A C7A 118.6(7) . . ? C5A C6A H1 120.7 . . ? C7A C6A H1 120.7 . . ? C8A C7A C6A 121.8(7) . . ? C8A C7A S1A 119.7(6) . . ? C6A C7A S1A 118.4(5) . . ? C7A C8A C9A 117.8(7) . . ? C7A C8A H8A 121.1 . . ? C9A C8A H8A 121.1 . . ? C4A C9A C8A 120.8(7) . . ? C4A C9A H9A 119.6 . . ? C8A C9A H9A 119.6 . . ? O5A C10A O6A 124.8(7) . . ? O5A C10A C11A 123.2(6) . . ? O6A C10A C11A 112.0(6) . . ? N1A C11A C10A 112.4(6) . . ? N1A C11A C12A 110.7(5) . . ? C10A C11A C12A 108.3(6) . . ? N1A C11A H11A 108.4 . . ? C10A C11A H11A 108.4 . . ? C12A C11A H11A 108.4 . . ? C13A C12A C11A 110.8(6) . . ? C13A C12A H12A 109.5 . . ? C11A C12A H12A 109.5 . . ? C13A C12A H12B 109.5 . . ? C11A C12A H12B 109.5 . . ? H12A C12A H12B 108.1 . . ? C18A C13A C14A 118.5(9) . . ? C18A C13A C12A 120.3(7) . . ? C14A C13A C12A 121.1(8) . . ? C13A C14A C15A 119.0(9) . . ? C13A C14A H14A 120.5 . . ? C15A C14A H14A 120.5 . . ? C16A C15A C14A 120.7(8) . . ? C16A C15A H15A 119.7 . . ? C14A C15A H15A 119.7 . . ? C15A C16A C17A 120.2(10) . . ? C15A C16A H16A 119.9 . . ? C17A C16A H16A 119.9 . . ? C16A C17A C18A 120.2(9) . . ? C16A C17A H17A 119.9 . . ? C18A C17A H17A 119.9 . . ? C17A C18A C13A 121.3(8) . . ? C17A C18A H18A 119.4 . . ? C13A C18A H18A 119.4 . . ? O4B S1B O3B 120.0(3) . . ? O4B S1B N1B 107.8(3) . . ? O3B S1B N1B 105.3(3) . . ? O4B S1B C7B 107.6(3) . . ? O3B S1B C7B 108.2(3) . . ? N1B S1B C7B 107.3(3) . . ? C1B O2B H2B 109.5(16) . . ? C10B O6B H6B 110.6(17) . . ? C11B N1B S1B 120.6(5) . . ? C11B N1B H2 114(5) . . ? S1B N1B H2 116(5) . . ? O1B C1B O2B 124.7(7) . . ? O1B C1B C2B 120.6(7) . . ? O2B C1B C2B 114.7(6) . . ? C3B C2B C1B 124.6(7) . . ? C3B C2B H3 117.7 . . ? C1B C2B H3 117.7 . . ? C2B C3B C4B 126.9(7) . . ? C2B C3B H3B 116.6 . . ? C4B C3B H3B 116.6 . . ? C9B C4B C5B 118.5(7) . . ? C9B C4B C3B 119.7(7) . . ? C5B C4B C3B 121.9(7) . . ? C4B C5B C6B 121.1(7) . . ? C4B C5B H5B 119.4 . . ? C6B C5B H5B 119.4 . . ? C7B C6B C5B 118.7(7) . . ? C7B C6B H4 120.7 . . ? C5B C6B H4 120.7 . . ? C8B C7B C6B 121.7(8) . . ? C8B C7B S1B 118.2(6) . . ? C6B C7B S1B 119.8(6) . . ? C7B C8B C9B 119.2(7) . . ? C7B C8B H8B 120.4 . . ? C9B C8B H8B 120.4 . . ? C4B C9B C8B 120.8(7) . . ? C4B C9B H9B 119.6 . . ? C8B C9B H9B 119.6 . . ? O5B C10B O6B 124.4(7) . . ? O5B C10B C11B 120.3(7) . . ? O6B C10B C11B 115.3(6) . . ? N1B C11B C12B 109.6(6) . . ? N1B C11B C10B 111.8(6) . . ? C12B C11B C10B 107.1(6) . . ? N1B C11B H11B 109.4 . . ? C12B C11B H11B 109.4 . . ? C10B C11B H11B 109.4 . . ? C11B C12B C13B 113.4(6) . . ? C11B C12B H12C 108.9 . . ? C13B C12B H12C 108.9 . . ? C11B C12B H12D 108.9 . . ? C13B C12B H12D 108.9 . . ? H12C C12B H12D 107.7 . . ? C14B C13B C18B 119.3(8) . . ? C14B C13B C12B 119.5(8) . . ? C18B C13B C12B 121.2(8) . . ? C13B C14B C15B 121.3(9) . . ? C13B C14B H14B 119.4 . . ? C15B C14B H14B 119.4 . . ? C16B C15B C14B 118.5(9) . . ? C16B C15B H15B 120.8 . . ? C14B C15B H15B 120.8 . . ? C15B C16B C17B 121.9(9) . . ? C15B C16B H16B 119.1 . . ? C17B C16B H16B 119.1 . . ? C16B C17B C18B 118.5(9) . . ? C16B C17B H17B 120.7 . . ? C18B C17B H17B 120.7 . . ? C13B C18B C17B 120.5(8) . . ? C13B C18B H18B 119.7 . . ? C17B C18B H18B 119.7 . . ? 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 O4A S1A N1A C11A 49.8(6) . . . . ? O3A S1A N1A C11A 178.5(5) . . . . ? C7A S1A N1A C11A -66.5(5) . . . . ? O2A C1A C2A C3A 5.1(14) . . . . ? O1A C1A C2A C3A -173.0(7) . . . . ? C1A C2A C3A C4A 176.9(8) . . . . ? C2A C3A C4A C5A 9.5(13) . . . . ? C2A C3A C4A C9A -169.1(8) . . . . ? C9A C4A C5A C6A -0.4(13) . . . . ? C3A C4A C5A C6A -179.0(8) . . . . ? C4A C5A C6A C7A 0.5(13) . . . . ? C5A C6A C7A C8A 0.6(13) . . . . ? C5A C6A C7A S1A 176.5(6) . . . . ? O4A S1A C7A C8A -7.5(7) . . . . ? O3A S1A C7A C8A -139.0(6) . . . . ? N1A S1A C7A C8A 107.9(6) . . . . ? O4A S1A C7A C6A 176.5(6) . . . . ? O3A S1A C7A C6A 45.1(7) . . . . ? N1A S1A C7A C6A -68.0(7) . . . . ? C6A C7A C8A C9A -1.7(12) . . . . ? S1A C7A C8A C9A -177.5(6) . . . . ? C5A C4A C9A C8A -0.7(12) . . . . ? C3A C4A C9A C8A 177.9(7) . . . . ? C7A C8A C9A C4A 1.8(11) . . . . ? S1A N1A C11A C10A 78.4(7) . . . . ? S1A N1A C11A C12A -160.3(5) . . . . ? O5A C10A C11A N1A 42.6(10) . . . . ? O6A C10A C11A N1A -139.0(6) . . . . ? O5A C10A C11A C12A -80.1(9) . . . . ? O6A C10A C11A C12A 98.4(7) . . . . ? N1A C11A C12A C13A 65.7(8) . . . . ? C10A C11A C12A C13A -170.6(6) . . . . ? C11A C12A C13A C18A 75.2(9) . . . . ? C11A C12A C13A C14A -106.4(8) . . . . ? C18A C13A C14A C15A -2.5(11) . . . . ? C12A C13A C14A C15A 179.0(7) . . . . ? C13A C14A C15A C16A 1.1(13) . . . . ? C14A C15A C16A C17A 0.9(15) . . . . ? C15A C16A C17A C18A -1.5(16) . . . . ? C16A C17A C18A C13A 0.0(14) . . . . ? C14A C13A C18A C17A 2.0(12) . . . . ? C12A C13A C18A C17A -179.6(8) . . . . ? O4B S1B N1B C11B 49.5(6) . . . . ? O3B S1B N1B C11B 178.7(5) . . . . ? C7B S1B N1B C11B -66.1(6) . . . . ? O1B C1B C2B C3B -175.6(8) . . . . ? O2B C1B C2B C3B 5.9(13) . . . . ? C1B C2B C3B C4B -175.8(8) . . . . ? C2B C3B C4B C9B -171.3(8) . . . . ? C2B C3B C4B C5B 10.1(13) . . . . ? C9B C4B C5B C6B -0.5(12) . . . . ? C3B C4B C5B C6B 178.1(8) . . . . ? C4B C5B C6B C7B -0.2(12) . . . . ? C5B C6B C7B C8B -0.2(12) . . . . ? C5B C6B C7B S1B -173.7(6) . . . . ? O4B S1B C7B C8B 163.3(6) . . . . ? O3B S1B C7B C8B 32.2(7) . . . . ? N1B S1B C7B C8B -81.0(6) . . . . ? O4B S1B C7B C6B -23.0(7) . . . . ? O3B S1B C7B C6B -154.0(6) . . . . ? N1B S1B C7B C6B 92.7(6) . . . . ? C6B C7B C8B C9B 1.4(11) . . . . ? S1B C7B C8B C9B 175.0(6) . . . . ? C5B C4B C9B C8B 1.6(11) . . . . ? C3B C4B C9B C8B -177.0(7) . . . . ? C7B C8B C9B C4B -2.1(11) . . . . ? S1B N1B C11B C12B -161.5(5) . . . . ? S1B N1B C11B C10B 79.9(7) . . . . ? O5B C10B C11B N1B 36.1(9) . . . . ? O6B C10B C11B N1B -145.7(6) . . . . ? O5B C10B C11B C12B -83.9(9) . . . . ? O6B C10B C11B C12B 94.3(7) . . . . ? N1B C11B C12B C13B 63.6(9) . . . . ? C10B C11B C12B C13B -174.9(6) . . . . ? C11B C12B C13B C14B 70.1(10) . . . . ? C11B C12B C13B C18B -108.9(9) . . . . ? C18B C13B C14B C15B -2.4(13) . . . . ? C12B C13B C14B C15B 178.5(8) . . . . ? C13B C14B C15B C16B 3.0(13) . . . . ? C14B C15B C16B C17B -2.6(15) . . . . ? C15B C16B C17B C18B 1.6(15) . . . . ? C14B C13B C18B C17B 1.4(13) . . . . ? C12B C13B C18B C17B -179.5(8) . . . . ? C16B C17B C18B C13B -1.0(14) . . . . ? 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 O6A H6A O1B 0.82(2) 1.88(3) 2.661(7) 157(7) . O2B H2B O5A 0.83(2) 1.84(2) 2.668(7) 174(7) . O6B H6B O2A 0.84(2) 1.82(3) 2.643(7) 166(7) . O1A H1A O5B 0.85(2) 1.86(4) 2.617(7) 148(7) . N1B H2 O1B 0.842(10) 2.155(19) 2.984(7) 168(6) 1_655 N1A H13 O4B 0.839(10) 2.21(3) 2.976(6) 152(6) 1_454 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 67.46 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.261 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.060 data_kaw104 _database_code_depnum_ccdc_archive 'CCDC 895732' #TrackingRef '- wheeler-ChemComm13.CIF' # (R)-1, reacted _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H34 N2 O12 S2' _chemical_formula_sum 'C36 H34 N2 O12 S2' _chemical_formula_weight 750.79 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.3597(5) _cell_length_b 13.9938(7) _cell_length_c 11.8314(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.721(3) _cell_angle_gamma 90.00 _cell_volume 1699.67(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8033 _cell_measurement_theta_min 3.104 _cell_measurement_theta_max 67.552 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 2.023 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5593 _exptl_absorpt_correction_T_max 0.9271 _exptl_absorpt_process_details 'SADABS (Bruker, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 22398 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 67.34 _reflns_number_total 5905 _reflns_number_gt 4578 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2008) and XPREP (Bruker, 2008) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _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. All non-hydrogen atoms were located in a single difference Fourier map and refined with anisotropic thermal parameters. UV irradiation of this sample using a 360 nm cut-on filter for 1 hr produced a crystal consisting of both reactant and product phases. This disorder and reaction conversion was determined by refining the occupancy factors to give a 81:19 ratio of reactant to photoproduct. The aryl groups of the product phase were restrained to be similar to aryl groups of the reactant phases using the SAME command. C4x - C9x and C4y - C9y were constrained using DELU and ISOR comamnd. The ring consisting of C4x - C9x was further constrained using FLAT. The N-H and O-H hydrogen atoms were located in difference density Fourier maps and refined with the O/N-H bonds restrained to 0.85(2) angstroms and Uiso = 1.2Ueq of the corresponding O/N atoms. All other H atoms were place in calculated positions and refined with Uiso = 1.2Ueq of the corresponding C atom (Uiso = 1.5eq for methyl C-H groups). ; _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^)+(0.0737P)^2^+0.3505P] 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 0.01(2) _refine_ls_number_reflns 5905 _refine_ls_number_parameters 633 _refine_ls_number_restraints 164 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.034 _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 S1A S 0.17329(10) 0.28502(8) 0.40220(9) 0.0443(3) Uani 1 1 d . . . O1A O 1.0102(3) 0.3267(3) 0.7193(3) 0.0631(10) Uani 1 1 d D A . H1 H 1.080(3) 0.318(4) 0.765(4) 0.076 Uiso 1 1 d D . . O2A O 0.9277(3) 0.2316(3) 0.8448(3) 0.0560(9) Uani 1 1 d . A . O3A O 0.3486(3) 0.4992(3) 0.5384(2) 0.0588(9) Uani 1 1 d . . . O4A O 0.2347(3) 0.4605(3) 0.6808(2) 0.0560(9) Uani 1 1 d D . . H2 H 0.307(3) 0.469(4) 0.724(3) 0.067 Uiso 1 1 d D . . O5A O 0.1897(3) 0.2548(2) 0.2893(3) 0.0580(9) Uani 1 1 d . A . O6A O 0.0738(3) 0.2442(3) 0.4579(3) 0.0559(9) Uani 1 1 d . A . N1A N 0.1480(3) 0.3992(3) 0.3922(3) 0.0430(9) Uani 1 1 d D A . H5 H 0.193(4) 0.426(3) 0.351(3) 0.052 Uiso 1 1 d D . . C1A C 0.9175(4) 0.2787(4) 0.7562(4) 0.0438(10) Uani 1 1 d . . . C2A C 0.7946(5) 0.2823(5) 0.6776(4) 0.0415(13) Uani 0.806(6) 1 d P A 1 H2A H 0.7949 0.3130 0.6080 0.050 Uiso 0.806(6) 1 calc PR A 1 C3A C 0.6831(5) 0.2444(4) 0.7003(4) 0.0375(13) Uani 0.806(6) 1 d P A 1 H3A H 0.6844 0.2115 0.7687 0.045 Uiso 0.806(6) 1 calc PR A 1 C4A C 0.5582(5) 0.2503(4) 0.6258(5) 0.0355(13) Uani 0.806(6) 1 d PD A 1 C5A C 0.5502(6) 0.2856(6) 0.5150(5) 0.0492(17) Uani 0.806(6) 1 d PD A 1 H5A H 0.6265 0.3028 0.4867 0.059 Uiso 0.806(6) 1 calc PR A 1 C6A C 0.4340(7) 0.2956(7) 0.4466(6) 0.055(2) Uani 0.806(6) 1 d PD A 1 H6A H 0.4302 0.3210 0.3736 0.067 Uiso 0.806(6) 1 calc PR A 1 C7A C 0.3224(6) 0.2671(6) 0.4885(5) 0.039(2) Uani 0.806(6) 1 d PD A 1 C8A C 0.3253(7) 0.2305(8) 0.5969(7) 0.044(2) Uani 0.806(6) 1 d PD A 1 H8A H 0.2488 0.2119 0.6240 0.053 Uiso 0.806(6) 1 calc PR A 1 C9A C 0.4449(6) 0.2218(5) 0.6648(5) 0.0401(16) Uani 0.806(6) 1 d PD A 1 H9A H 0.4486 0.1964 0.7378 0.048 Uiso 0.806(6) 1 calc PR A 1 C10A C 0.2466(4) 0.4722(4) 0.5733(3) 0.0430(11) Uani 1 1 d . A . C11A C 0.1235(4) 0.4530(3) 0.4927(3) 0.0402(10) Uani 1 1 d . . . H11A H 0.0654 0.4148 0.5336 0.048 Uiso 1 1 calc R A . C12A C 0.0562(4) 0.5475(4) 0.4604(4) 0.0496(12) Uani 1 1 d . A . H12A H 0.0515 0.5846 0.5290 0.060 Uiso 1 1 calc R . . H12B H 0.1076 0.5834 0.4123 0.060 Uiso 1 1 calc R . . C13A C -0.0789(5) 0.5340(3) 0.3984(4) 0.0457(11) Uani 1 1 d . . . C14A C -0.1078(6) 0.5479(4) 0.2825(4) 0.0628(14) Uani 1 1 d . A . H14A H -0.0427 0.5675 0.2407 0.075 Uiso 1 1 calc R . . C15A C -0.2332(7) 0.5330(5) 0.2272(5) 0.090(2) Uani 1 1 d . . . H15A H -0.2513 0.5418 0.1488 0.108 Uiso 1 1 calc R A . C16A C -0.3302(6) 0.5054(5) 0.2883(8) 0.100(3) Uani 1 1 d . A . H16A H -0.4139 0.4945 0.2513 0.120 Uiso 1 1 calc R . . C17A C -0.3034(5) 0.4939(5) 0.4041(7) 0.0861(19) Uani 1 1 d . . . H17A H -0.3698 0.4772 0.4459 0.103 Uiso 1 1 calc R A . C18A C -0.1797(5) 0.5070(4) 0.4585(5) 0.0617(14) Uani 1 1 d . A . H18A H -0.1626 0.4978 0.5369 0.074 Uiso 1 1 calc R . . S1B S 1.32561(9) 0.48980(9) 1.10503(8) 0.0413(3) Uani 1 1 d . . . O1B O 0.4614(3) 0.4627(3) 0.8156(2) 0.0499(8) Uani 1 1 d . A . H3 H 0.501(3) 0.506(4) 0.630(3) 0.060 Uiso 1 1 d D . . O2B O 0.5723(3) 0.5121(3) 0.6769(2) 0.0530(9) Uani 1 1 d D A . O3B O 1.1452(3) 0.2296(3) 0.9937(3) 0.0603(10) Uani 1 1 d D . . O4B O 1.2244(3) 0.3243(3) 0.8675(3) 0.0564(9) Uani 1 1 d . . . H4 H 1.075(3) 0.230(4) 0.950(4) 0.068 Uiso 1 1 d D . . O5B O 1.3131(3) 0.4614(2) 1.2190(2) 0.0496(8) Uani 1 1 d . A . O6B O 1.3977(3) 0.5735(2) 1.0863(2) 0.0499(8) Uani 1 1 d . A . N1B N 1.3966(3) 0.4026(3) 1.0463(3) 0.0445(9) Uani 1 1 d D A . H6 H 1.409(5) 0.423(3) 0.982(2) 0.053 Uiso 1 1 d D . . C1B C 0.5638(4) 0.4849(4) 0.7801(3) 0.0432(10) Uani 1 1 d . . . C2B C 0.6886(5) 0.4873(4) 0.8598(4) 0.0371(12) Uani 0.806(6) 1 d P A 1 H2B H 0.6880 0.4654 0.9339 0.045 Uiso 0.806(6) 1 calc PR A 1 C3B C 0.7995(4) 0.5186(4) 0.8308(4) 0.0366(13) Uani 0.806(6) 1 d P A 1 H3B H 0.7970 0.5456 0.7587 0.044 Uiso 0.806(6) 1 calc PR A 1 C4B C 0.9267(5) 0.5148(5) 0.9022(4) 0.0348(13) Uani 0.806(6) 1 d PD A 1 C5B C 0.9440(5) 0.4654(5) 1.0041(5) 0.0397(14) Uani 0.806(6) 1 d PD A 1 H5B H 0.8736 0.4347 1.0295 0.048 Uiso 0.806(6) 1 calc PR A 1 C6B C 1.0646(5) 0.4612(5) 1.0684(5) 0.0379(15) Uani 0.806(6) 1 d PD A 1 H6B H 1.0757 0.4284 1.1374 0.045 Uiso 0.806(6) 1 calc PR A 1 C7B C 1.1696(5) 0.5062(5) 1.0296(5) 0.0307(14) Uani 0.806(6) 1 d PD A 1 C8B C 1.1530(6) 0.5565(5) 0.9292(6) 0.0384(17) Uani 0.806(6) 1 d PD A 1 H8B H 1.2235 0.5872 0.9041 0.046 Uiso 0.806(6) 1 calc PR A 1 C9B C 1.0325(6) 0.5615(5) 0.8662(5) 0.0427(17) Uani 0.806(6) 1 d PD A 1 H9B H 1.0212 0.5964 0.7987 0.051 Uiso 0.806(6) 1 calc PR A 1 C10B C 1.2302(4) 0.2867(4) 0.9610(4) 0.0463(11) Uani 1 1 d . A . C11B C 1.3485(4) 0.3066(4) 1.0504(4) 0.0465(11) Uani 1 1 d . . . H11B H 1.3247 0.2944 1.1265 0.056 Uiso 1 1 calc R A . C12B C 1.4544(4) 0.2354(4) 1.0272(4) 0.0562(13) Uani 1 1 d . A . H12C H 1.4190 0.1713 1.0277 0.067 Uiso 1 1 calc R . . H12D H 1.4769 0.2474 0.9515 0.067 Uiso 1 1 calc R . . C13B C 1.5774(5) 0.2401(4) 1.1124(5) 0.0560(13) Uani 1 1 d . . . C14B C 1.5722(6) 0.2075(4) 1.2198(5) 0.0679(15) Uani 1 1 d . A . H14B H 1.4934 0.1852 1.2389 0.081 Uiso 1 1 calc R . . C15B C 1.6808(7) 0.2064(5) 1.3015(6) 0.087(2) Uani 1 1 d . . . H15B H 1.6761 0.1811 1.3735 0.105 Uiso 1 1 calc R A . C16B C 1.7938(7) 0.2425(5) 1.2753(7) 0.088(2) Uani 1 1 d . A . H16B H 1.8658 0.2457 1.3313 0.106 Uiso 1 1 calc R . . C17B C 1.8040(6) 0.2746(5) 1.1680(7) 0.086(2) Uani 1 1 d . . . H17B H 1.8834 0.2970 1.1503 0.103 Uiso 1 1 calc R A . C18B C 1.6940(5) 0.2735(4) 1.0842(6) 0.0763(18) Uani 1 1 d . A . H18B H 1.6999 0.2951 1.0107 0.092 Uiso 1 1 calc R . . C2X C 0.806(3) 0.344(2) 0.717(2) 0.054(6) Uani 0.194(6) 1 d PU A 2 H2X H 0.7971 0.3525 0.6339 0.065 Uiso 0.194(6) 1 calc PR A 2 C3X C 0.676(2) 0.317(2) 0.754(2) 0.054(6) Uani 0.194(6) 1 d PU A 2 H3X H 0.6896 0.2639 0.8087 0.065 Uiso 0.194(6) 1 calc PR A 2 C4X C 0.561(2) 0.291(2) 0.658(2) 0.048(6) Uani 0.194(6) 1 d PDU A 2 C5X C 0.553(2) 0.3227(19) 0.546(2) 0.052(6) Uani 0.194(6) 1 d PDU A 2 H5X H 0.6278 0.3472 0.5209 0.063 Uiso 0.194(6) 1 calc PR A 2 C6X C 0.442(3) 0.320(2) 0.4716(19) 0.048(7) Uani 0.194(6) 1 d PDU A 2 H6X H 0.4407 0.3395 0.3965 0.058 Uiso 0.194(6) 1 calc PR A 2 C7X C 0.329(2) 0.286(3) 0.510(2) 0.038(7) Uani 0.194(6) 1 d PDU A 2 C8X C 0.335(3) 0.247(3) 0.618(3) 0.040(7) Uani 0.194(6) 1 d PDU A 2 H8X H 0.2636 0.2144 0.6390 0.048 Uiso 0.194(6) 1 calc PR A 2 C9X C 0.448(2) 0.256(2) 0.6941(19) 0.044(6) Uani 0.194(6) 1 d PDU A 2 H9X H 0.4474 0.2396 0.7701 0.053 Uiso 0.194(6) 1 calc PR A 2 C2Y C 0.674(3) 0.418(2) 0.823(2) 0.056(6) Uani 0.194(6) 1 d PU A 2 H2Y H 0.6837 0.4090 0.9058 0.068 Uiso 0.194(6) 1 calc PR A 2 C3Y C 0.805(3) 0.443(2) 0.779(2) 0.059(6) Uani 0.194(6) 1 d PU A 2 H3Y H 0.7947 0.4958 0.7247 0.071 Uiso 0.194(6) 1 calc PR A 2 C4Y C 0.925(2) 0.464(2) 0.883(2) 0.052(6) Uani 0.194(6) 1 d PDU A 2 C5Y C 0.942(2) 0.413(2) 0.9832(19) 0.049(5) Uani 0.194(6) 1 d PDU A 2 H5Y H 0.8745 0.3756 1.0025 0.059 Uiso 0.194(6) 1 calc PR A 2 C6Y C 1.057(2) 0.417(2) 1.055(2) 0.051(7) Uani 0.194(6) 1 d PDU A 2 H6Y H 1.0675 0.3824 1.1227 0.061 Uiso 0.194(6) 1 calc PR A 2 C7Y C 1.158(2) 0.474(2) 1.028(2) 0.040(6) Uani 0.194(6) 1 d PDU A 2 C8Y C 1.141(3) 0.525(3) 0.928(3) 0.050(7) Uani 0.194(6) 1 d PDU A 2 H8Y H 1.2093 0.5610 0.9080 0.060 Uiso 0.194(6) 1 calc PR A 2 C9Y C 1.024(3) 0.524(2) 0.857(2) 0.046(6) Uani 0.194(6) 1 d PDU A 2 H9Y H 1.0114 0.5633 0.7932 0.055 Uiso 0.194(6) 1 calc PR A 2 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 S1A 0.0385(6) 0.0483(7) 0.0434(6) 0.0030(5) -0.0041(4) -0.0011(5) O1A 0.0421(19) 0.101(3) 0.0426(18) 0.0082(19) -0.0067(14) -0.019(2) O2A 0.0389(17) 0.062(2) 0.062(2) 0.0129(18) -0.0105(14) -0.0057(16) O3A 0.0357(16) 0.097(3) 0.0425(16) -0.0105(19) 0.0024(12) -0.0143(19) O4A 0.0363(16) 0.098(3) 0.0321(16) 0.0006(17) -0.0019(12) -0.0066(17) O5A 0.059(2) 0.061(2) 0.052(2) -0.0027(16) -0.0010(15) 0.0012(17) O6A 0.0390(16) 0.064(2) 0.061(2) 0.0131(17) -0.0075(14) -0.0079(16) N1A 0.0334(19) 0.061(2) 0.0340(19) 0.0011(18) 0.0018(14) -0.0073(17) C1A 0.038(2) 0.054(3) 0.038(2) -0.007(2) 0.0014(18) -0.003(2) C2A 0.037(3) 0.051(4) 0.035(3) 0.001(3) -0.001(2) 0.002(3) C3A 0.034(3) 0.038(3) 0.039(3) 0.003(2) 0.002(2) 0.006(2) C4A 0.035(3) 0.032(3) 0.037(3) 0.001(3) -0.004(2) 0.004(3) C5A 0.032(3) 0.071(5) 0.045(3) 0.009(4) 0.006(3) 0.001(3) C6A 0.044(4) 0.080(6) 0.041(4) 0.007(4) -0.001(3) -0.008(4) C7A 0.035(3) 0.047(5) 0.033(3) -0.007(3) -0.004(2) -0.001(3) C8A 0.032(3) 0.048(6) 0.049(4) 0.001(4) -0.002(3) -0.010(3) C9A 0.045(3) 0.043(4) 0.031(3) 0.003(3) -0.001(2) -0.005(3) C10A 0.031(2) 0.056(3) 0.040(2) 0.000(2) 0.0001(16) -0.001(2) C11A 0.029(2) 0.050(3) 0.040(2) -0.006(2) 0.0008(16) -0.0019(19) C12A 0.040(2) 0.050(3) 0.057(3) -0.008(2) 0.001(2) 0.002(2) C13A 0.044(3) 0.041(3) 0.049(3) -0.002(2) -0.007(2) 0.007(2) C14A 0.070(4) 0.058(3) 0.058(3) -0.002(3) -0.002(3) 0.017(3) C15A 0.106(6) 0.080(5) 0.068(4) -0.032(3) -0.046(4) 0.042(4) C16A 0.049(4) 0.082(5) 0.155(7) -0.055(5) -0.039(4) 0.018(4) C17A 0.042(3) 0.074(4) 0.141(6) -0.007(5) 0.006(3) -0.005(3) C18A 0.045(3) 0.060(4) 0.079(4) 0.012(3) 0.009(2) 0.001(3) S1B 0.0325(5) 0.0566(7) 0.0339(5) 0.0001(5) 0.0007(4) 0.0001(5) O1B 0.0317(15) 0.075(2) 0.0421(16) 0.0051(16) 0.0031(12) -0.0083(15) O2B 0.0376(17) 0.081(3) 0.0386(16) 0.0036(17) -0.0014(12) -0.0105(17) O3B 0.0426(18) 0.070(2) 0.062(2) 0.0147(18) -0.0172(15) -0.0148(18) O4B 0.0394(17) 0.084(3) 0.0430(18) 0.0091(18) -0.0055(13) -0.0148(17) O5B 0.0348(15) 0.075(2) 0.0376(15) 0.0048(15) -0.0010(12) -0.0010(15) O6B 0.0495(18) 0.056(2) 0.0429(18) 0.0021(15) 0.0015(14) -0.0052(16) N1B 0.0327(18) 0.060(2) 0.039(2) 0.0062(19) -0.0001(15) -0.0065(18) C1B 0.036(2) 0.056(3) 0.037(2) -0.001(2) 0.0019(16) 0.001(2) C2B 0.036(3) 0.039(3) 0.035(2) 0.001(3) 0.0009(19) -0.002(2) C3B 0.029(3) 0.044(3) 0.036(3) -0.004(2) 0.001(2) -0.005(2) C4B 0.031(3) 0.034(3) 0.039(3) -0.003(3) 0.001(2) 0.003(2) C5B 0.032(3) 0.043(4) 0.045(3) 0.007(3) 0.009(2) -0.006(3) C6B 0.034(3) 0.042(4) 0.037(3) 0.008(3) 0.004(2) 0.001(3) C7B 0.028(3) 0.029(4) 0.033(3) -0.001(3) 0.0011(18) -0.002(3) C8B 0.032(3) 0.042(5) 0.040(3) 0.010(3) 0.004(2) -0.002(3) C9B 0.040(3) 0.046(4) 0.042(3) 0.011(3) 0.005(2) -0.005(3) C10B 0.032(2) 0.054(3) 0.051(3) 0.009(2) 0.0013(18) -0.008(2) C11B 0.036(2) 0.056(3) 0.045(2) 0.001(2) -0.0040(18) -0.003(2) C12B 0.044(3) 0.059(3) 0.060(3) -0.009(3) -0.013(2) -0.006(3) C13B 0.047(3) 0.045(3) 0.071(3) 0.002(3) -0.013(2) 0.007(3) C14B 0.062(3) 0.055(3) 0.079(4) -0.003(3) -0.016(3) 0.011(3) C15B 0.088(5) 0.067(4) 0.097(5) -0.002(4) -0.026(4) 0.018(4) C16B 0.076(5) 0.055(4) 0.117(6) -0.003(4) -0.050(4) 0.003(4) C17B 0.053(3) 0.055(4) 0.140(6) 0.009(4) -0.019(4) -0.006(3) C18B 0.044(3) 0.058(4) 0.120(5) 0.016(3) -0.012(3) -0.001(3) C2X 0.055(8) 0.055(10) 0.053(10) 0.001(8) 0.014(7) -0.002(8) C3X 0.043(7) 0.063(10) 0.054(8) 0.005(8) -0.001(6) -0.003(7) C4X 0.044(7) 0.047(11) 0.052(8) 0.003(8) 0.006(6) 0.008(8) C5X 0.048(8) 0.060(12) 0.050(8) -0.004(8) 0.012(6) -0.006(8) C6X 0.054(9) 0.054(12) 0.040(9) -0.001(8) 0.016(6) -0.002(8) C7X 0.038(7) 0.038(7) 0.038(7) 0.0000(10) 0.0048(14) 0.0001(10) C8X 0.047(9) 0.038(12) 0.035(9) -0.003(8) 0.009(7) 0.000(8) C9X 0.039(8) 0.048(11) 0.046(9) 0.001(8) 0.002(6) 0.002(7) C2Y 0.052(8) 0.062(11) 0.057(10) 0.006(8) 0.011(7) -0.002(8) C3Y 0.048(8) 0.067(11) 0.060(9) 0.002(8) 0.004(6) -0.005(8) C4Y 0.048(8) 0.052(10) 0.059(8) -0.004(7) 0.009(6) 0.002(8) C5Y 0.043(8) 0.050(10) 0.055(8) -0.004(7) 0.011(6) -0.008(8) C6Y 0.049(9) 0.045(11) 0.058(9) -0.001(8) 0.007(6) -0.011(8) C7Y 0.040(6) 0.040(6) 0.040(6) -0.0001(10) 0.0052(13) 0.0001(10) C8Y 0.050(9) 0.050(12) 0.050(10) -0.001(8) 0.007(7) -0.006(8) C9Y 0.042(8) 0.043(11) 0.051(9) 0.006(8) 0.003(6) 0.009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1A O6A 1.416(3) . ? S1A O5A 1.433(3) . ? S1A N1A 1.621(4) . ? S1A C7A 1.752(6) . ? S1A C7X 1.92(2) . ? O1A C1A 1.296(6) . ? O1A H1 0.85(2) . ? O2A C1A 1.231(5) . ? O3A C10A 1.244(5) . ? O4A C10A 1.304(5) . ? O4A H2 0.85(2) . ? N1A C11A 1.458(5) . ? N1A H5 0.808(19) . ? C1A C2A 1.473(6) . ? C1A C2X 1.50(3) . ? C2A C3A 1.331(8) . ? C2A H2A 0.9300 . ? C3A C4A 1.466(7) . ? C3A H3A 0.9300 . ? C4A C9A 1.376(7) . ? C4A C5A 1.393(7) . ? C5A C6A 1.365(7) . ? C5A H5A 0.9300 . ? C6A C7A 1.377(7) . ? C6A H6A 0.9300 . ? C7A C8A 1.378(7) . ? C8A C9A 1.389(7) . ? C8A H8A 0.9300 . ? C9A H9A 0.9300 . ? C10A C11A 1.510(5) . ? C11A C12A 1.520(7) . ? C11A H11A 0.9800 . ? C12A C13A 1.502(6) . ? C12A H12A 0.9700 . ? C12A H12B 0.9700 . ? C13A C14A 1.378(7) . ? C13A C18A 1.392(7) . ? C14A C15A 1.389(8) . ? C14A H14A 0.9300 . ? C15A C16A 1.369(10) . ? C15A H15A 0.9300 . ? C16A C17A 1.370(10) . ? C16A H16A 0.9300 . ? C17A C18A 1.367(7) . ? C17A H17A 0.9300 . ? C18A H18A 0.9300 . ? S1B O6B 1.422(3) . ? S1B O5B 1.428(3) . ? S1B N1B 1.628(4) . ? S1B C7B 1.753(5) . ? S1B C7Y 1.87(2) . ? O1B C1B 1.232(5) . ? O2B C1B 1.293(5) . ? O2B H3 0.866(19) . ? O3B C10B 1.287(5) . ? O3B H4 0.84(2) . ? O4B C10B 1.220(5) . ? N1B C11B 1.436(6) . ? N1B H6 0.840(19) . ? C1B C2B 1.495(6) . ? C1B C2Y 1.51(3) . ? C2B C3B 1.317(7) . ? C2B H2B 0.9300 . ? C3B C4B 1.467(7) . ? C3B H3B 0.9300 . ? C4B C5B 1.381(7) . ? C4B C9B 1.392(8) . ? C5B C6B 1.373(7) . ? C5B H5B 0.9300 . ? C6B C7B 1.388(8) . ? C6B H6B 0.9300 . ? C7B C8B 1.371(7) . ? C8B C9B 1.367(7) . ? C8B H8B 0.9300 . ? C9B H9B 0.9300 . ? C10B C11B 1.532(6) . ? C11B C12B 1.533(7) . ? C11B H11B 0.9800 . ? C12B C13B 1.517(6) . ? C12B H12C 0.9700 . ? C12B H12D 0.9700 . ? C13B C14B 1.359(8) . ? C13B C18B 1.377(8) . ? C14B C15B 1.381(8) . ? C14B H14B 0.9300 . ? C15B C16B 1.349(10) . ? C15B H15B 0.9300 . ? C16B C17B 1.364(10) . ? C16B H16B 0.9300 . ? C17B C18B 1.406(8) . ? C17B H17B 0.9300 . ? C18B H18B 0.9300 . ? C2X C3X 1.52(3) . ? C2X C3Y 1.58(4) . ? C2X H2X 0.9800 . ? C3X C4X 1.57(3) . ? C3X C2Y 1.64(4) . ? C3X H3X 0.9800 . ? C4X C9X 1.388(16) . ? C4X C5X 1.397(16) . ? C5X C6X 1.354(16) . ? C5X H5X 0.9300 . ? C6X C7X 1.393(16) . ? C6X H6X 0.9300 . ? C7X C8X 1.380(16) . ? C8X C9X 1.383(16) . ? C8X H8X 0.9300 . ? C9X H9X 0.9300 . ? C2Y C3Y 1.56(4) . ? C2Y H2Y 0.9800 . ? C3Y C4Y 1.64(3) . ? C3Y H3Y 0.9800 . ? C4Y C5Y 1.377(18) . ? C4Y C9Y 1.389(18) . ? C5Y C6Y 1.372(17) . ? C5Y H5Y 0.9300 . ? C6Y C7Y 1.379(18) . ? C6Y H6Y 0.9300 . ? C7Y C8Y 1.369(18) . ? C8Y C9Y 1.376(17) . ? C8Y H8Y 0.9300 . ? C9Y H9Y 0.9300 . ? 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 O6A S1A O5A 120.0(2) . . ? O6A S1A N1A 108.1(2) . . ? O5A S1A N1A 105.12(19) . . ? O6A S1A C7A 108.1(3) . . ? O5A S1A C7A 107.2(3) . . ? N1A S1A C7A 107.8(3) . . ? O6A S1A C7X 107.0(9) . . ? O5A S1A C7X 115.5(10) . . ? N1A S1A C7X 98.7(12) . . ? C7A S1A C7X 10.5(13) . . ? C1A O1A H1 109(4) . . ? C10A O4A H2 112(3) . . ? C11A N1A S1A 119.5(3) . . ? C11A N1A H5 116(3) . . ? S1A N1A H5 113(4) . . ? O2A C1A O1A 125.6(4) . . ? O2A C1A C2A 121.6(4) . . ? O1A C1A C2A 112.7(4) . . ? O2A C1A C2X 124.5(10) . . ? O1A C1A C2X 99.0(11) . . ? C2A C1A C2X 38.3(12) . . ? C3A C2A C1A 124.0(5) . . ? C3A C2A H2A 118.0 . . ? C1A C2A H2A 118.0 . . ? C2A C3A C4A 125.2(5) . . ? C2A C3A H3A 117.4 . . ? C4A C3A H3A 117.4 . . ? C9A C4A C5A 118.2(5) . . ? C9A C4A C3A 120.3(5) . . ? C5A C4A C3A 121.4(5) . . ? C6A C5A C4A 122.0(5) . . ? C6A C5A H5A 119.0 . . ? C4A C5A H5A 119.0 . . ? C5A C6A C7A 118.2(5) . . ? C5A C6A H6A 120.9 . . ? C7A C6A H6A 120.9 . . ? C6A C7A C8A 122.0(5) . . ? C6A C7A S1A 117.7(5) . . ? C8A C7A S1A 120.2(5) . . ? C7A C8A C9A 118.5(5) . . ? C7A C8A H8A 120.8 . . ? C9A C8A H8A 120.8 . . ? C4A C9A C8A 121.0(5) . . ? C4A C9A H9A 119.5 . . ? C8A C9A H9A 119.5 . . ? O3A C10A O4A 123.9(4) . . ? O3A C10A C11A 121.8(4) . . ? O4A C10A C11A 114.3(3) . . ? N1A C11A C10A 112.5(3) . . ? N1A C11A C12A 111.6(4) . . ? C10A C11A C12A 108.9(4) . . ? N1A C11A H11A 107.9 . . ? C10A C11A H11A 107.9 . . ? C12A C11A H11A 107.9 . . ? C13A C12A C11A 112.3(4) . . ? C13A C12A H12A 109.2 . . ? C11A C12A H12A 109.2 . . ? C13A C12A H12B 109.2 . . ? C11A C12A H12B 109.2 . . ? H12A C12A H12B 107.9 . . ? C14A C13A C18A 117.9(5) . . ? C14A C13A C12A 122.1(5) . . ? C18A C13A C12A 119.9(4) . . ? C13A C14A C15A 120.8(6) . . ? C13A C14A H14A 119.6 . . ? C15A C14A H14A 119.6 . . ? C16A C15A C14A 120.0(6) . . ? C16A C15A H15A 120.0 . . ? C14A C15A H15A 120.0 . . ? C15A C16A C17A 119.7(6) . . ? C15A C16A H16A 120.1 . . ? C17A C16A H16A 120.1 . . ? C18A C17A C16A 120.4(6) . . ? C18A C17A H17A 119.8 . . ? C16A C17A H17A 119.8 . . ? C17A C18A C13A 121.1(6) . . ? C17A C18A H18A 119.5 . . ? C13A C18A H18A 119.5 . . ? O6B S1B O5B 119.48(19) . . ? O6B S1B N1B 105.90(19) . . ? O5B S1B N1B 107.3(2) . . ? O6B S1B C7B 106.3(3) . . ? O5B S1B C7B 108.9(2) . . ? N1B S1B C7B 108.6(2) . . ? O6B S1B C7Y 119.8(8) . . ? O5B S1B C7Y 103.5(8) . . ? N1B S1B C7Y 98.2(11) . . ? C7B S1B C7Y 14.6(9) . . ? C1B O2B H3 114(3) . . ? C10B O3B H4 113(4) . . ? C11B N1B S1B 120.5(3) . . ? C11B N1B H6 116(4) . . ? S1B N1B H6 106(3) . . ? O1B C1B O2B 124.5(4) . . ? O1B C1B C2B 120.2(4) . . ? O2B C1B C2B 115.2(4) . . ? O1B C1B C2Y 112.1(11) . . ? O2B C1B C2Y 110.7(11) . . ? C2B C1B C2Y 41.6(12) . . ? C3B C2B C1B 123.7(4) . . ? C3B C2B H2B 118.2 . . ? C1B C2B H2B 118.2 . . ? C2B C3B C4B 125.8(5) . . ? C2B C3B H3B 117.1 . . ? C4B C3B H3B 117.1 . . ? C5B C4B C9B 119.2(5) . . ? C5B C4B C3B 121.5(5) . . ? C9B C4B C3B 119.3(5) . . ? C6B C5B C4B 120.5(5) . . ? C6B C5B H5B 119.8 . . ? C4B C5B H5B 119.8 . . ? C5B C6B C7B 119.5(5) . . ? C5B C6B H6B 120.2 . . ? C7B C6B H6B 120.2 . . ? C8B C7B C6B 120.4(5) . . ? C8B C7B S1B 120.5(5) . . ? C6B C7B S1B 118.8(4) . . ? C9B C8B C7B 119.9(6) . . ? C9B C8B H8B 120.1 . . ? C7B C8B H8B 120.1 . . ? C8B C9B C4B 120.5(6) . . ? C8B C9B H9B 119.7 . . ? C4B C9B H9B 119.7 . . ? O4B C10B O3B 126.0(4) . . ? O4B C10B C11B 119.0(4) . . ? O3B C10B C11B 114.9(4) . . ? N1B C11B C10B 113.3(4) . . ? N1B C11B C12B 110.0(4) . . ? C10B C11B C12B 106.5(4) . . ? N1B C11B H11B 109.0 . . ? C10B C11B H11B 109.0 . . ? C12B C11B H11B 109.0 . . ? C13B C12B C11B 114.3(4) . . ? C13B C12B H12C 108.7 . . ? C11B C12B H12C 108.7 . . ? C13B C12B H12D 108.7 . . ? C11B C12B H12D 108.7 . . ? H12C C12B H12D 107.6 . . ? C14B C13B C18B 119.1(5) . . ? C14B C13B C12B 118.1(5) . . ? C18B C13B C12B 122.7(5) . . ? C13B C14B C15B 121.8(7) . . ? C13B C14B H14B 119.1 . . ? C15B C14B H14B 119.1 . . ? C16B C15B C14B 119.0(7) . . ? C16B C15B H15B 120.5 . . ? C14B C15B H15B 120.5 . . ? C15B C16B C17B 121.1(6) . . ? C15B C16B H16B 119.5 . . ? C17B C16B H16B 119.5 . . ? C16B C17B C18B 119.7(6) . . ? C16B C17B H17B 120.1 . . ? C18B C17B H17B 120.1 . . ? C13B C18B C17B 119.1(7) . . ? C13B C18B H18B 120.4 . . ? C17B C18B H18B 120.4 . . ? C1A C2X C3X 116(2) . . ? C1A C2X C3Y 116(2) . . ? C3X C2X C3Y 91(2) . . ? C1A C2X H2X 110.7 . . ? C3X C2X H2X 110.7 . . ? C3Y C2X H2X 110.7 . . ? C2X C3X C4X 118(2) . . ? C2X C3X C2Y 90(2) . . ? C4X C3X C2Y 120(2) . . ? C2X C3X H3X 109.2 . . ? C4X C3X H3X 109.2 . . ? C2Y C3X H3X 109.2 . . ? C9X C4X C5X 117.1(13) . . ? C9X C4X C3X 117.1(18) . . ? C5X C4X C3X 123.6(18) . . ? C6X C5X C4X 123.1(14) . . ? C6X C5X H5X 118.5 . . ? C4X C5X H5X 118.5 . . ? C5X C6X C7X 118.4(14) . . ? C5X C6X H6X 120.8 . . ? C7X C6X H6X 120.8 . . ? C8X C7X C6X 120.1(14) . . ? C8X C7X S1A 122.7(17) . . ? C6X C7X S1A 116.8(17) . . ? C7X C8X C9X 119.5(14) . . ? C7X C8X H8X 120.3 . . ? C9X C8X H8X 120.3 . . ? C8X C9X C4X 120.8(14) . . ? C8X C9X H9X 119.6 . . ? C4X C9X H9X 119.6 . . ? C1B C2Y C3Y 114(2) . . ? C1B C2Y C3X 115(2) . . ? C3Y C2Y C3X 88(2) . . ? C1B C2Y H2Y 112.6 . . ? C3Y C2Y H2Y 112.6 . . ? C3X C2Y H2Y 112.6 . . ? C2Y C3Y C2X 91(2) . . ? C2Y C3Y C4Y 113(2) . . ? C2X C3Y C4Y 117(2) . . ? C2Y C3Y H3Y 111.2 . . ? C2X C3Y H3Y 111.2 . . ? C4Y C3Y H3Y 111.2 . . ? C5Y C4Y C9Y 119.0(18) . . ? C5Y C4Y C3Y 123(2) . . ? C9Y C4Y C3Y 116.9(19) . . ? C6Y C5Y C4Y 121.1(19) . . ? C6Y C5Y H5Y 119.4 . . ? C4Y C5Y H5Y 119.4 . . ? C5Y C6Y C7Y 119.9(19) . . ? C5Y C6Y H6Y 120.1 . . ? C7Y C6Y H6Y 120.1 . . ? C8Y C7Y C6Y 119.1(19) . . ? C8Y C7Y S1B 111.3(16) . . ? C6Y C7Y S1B 129.5(17) . . ? C7Y C8Y C9Y 122(2) . . ? C7Y C8Y H8Y 119.2 . . ? C9Y C8Y H8Y 119.2 . . ? C8Y C9Y C4Y 119.1(19) . . ? C8Y C9Y H9Y 120.5 . . ? C4Y C9Y H9Y 120.5 . . ? 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 O6A S1A N1A C11A 49.0(3) . . . . ? O5A S1A N1A C11A 178.3(3) . . . . ? C7A S1A N1A C11A -67.6(4) . . . . ? C7X S1A N1A C11A -62.2(9) . . . . ? O2A C1A C2A C3A 7.1(9) . . . . ? O1A C1A C2A C3A -175.1(6) . . . . ? C2X C1A C2A C3A -100.0(17) . . . . ? C1A C2A C3A C4A 177.4(6) . . . . ? C2A C3A C4A C9A -169.7(6) . . . . ? C2A C3A C4A C5A 9.5(10) . . . . ? C9A C4A C5A C6A 2.3(11) . . . . ? C3A C4A C5A C6A -176.9(7) . . . . ? C4A C5A C6A C7A -1.9(13) . . . . ? C5A C6A C7A C8A 0.9(13) . . . . ? C5A C6A C7A S1A 177.3(7) . . . . ? O6A S1A C7A C6A 175.6(6) . . . . ? O5A S1A C7A C6A 44.9(7) . . . . ? N1A S1A C7A C6A -67.8(7) . . . . ? C7X S1A C7A C6A -99(6) . . . . ? O6A S1A C7A C8A -8.0(8) . . . . ? O5A S1A C7A C8A -138.6(7) . . . . ? N1A S1A C7A C8A 108.7(7) . . . . ? C7X S1A C7A C8A 78(6) . . . . ? C6A C7A C8A C9A -0.4(14) . . . . ? S1A C7A C8A C9A -176.7(7) . . . . ? C5A C4A C9A C8A -1.8(11) . . . . ? C3A C4A C9A C8A 177.5(7) . . . . ? C7A C8A C9A C4A 0.9(13) . . . . ? S1A N1A C11A C10A 77.5(4) . . . . ? S1A N1A C11A C12A -159.7(3) . . . . ? O3A C10A C11A N1A 44.1(6) . . . . ? O4A C10A C11A N1A -137.7(4) . . . . ? O3A C10A C11A C12A -80.1(6) . . . . ? O4A C10A C11A C12A 98.0(5) . . . . ? N1A C11A C12A C13A 66.0(5) . . . . ? C10A C11A C12A C13A -169.2(4) . . . . ? C11A C12A C13A C14A -105.0(5) . . . . ? C11A C12A C13A C18A 75.3(6) . . . . ? C18A C13A C14A C15A -1.6(8) . . . . ? C12A C13A C14A C15A 178.7(5) . . . . ? C13A C14A C15A C16A 0.9(9) . . . . ? C14A C15A C16A C17A 0.9(11) . . . . ? C15A C16A C17A C18A -2.0(11) . . . . ? C16A C17A C18A C13A 1.3(10) . . . . ? C14A C13A C18A C17A 0.6(8) . . . . ? C12A C13A C18A C17A -179.8(5) . . . . ? O6B S1B N1B C11B 179.6(3) . . . . ? O5B S1B N1B C11B 50.9(4) . . . . ? C7B S1B N1B C11B -66.7(4) . . . . ? C7Y S1B N1B C11B -56.1(8) . . . . ? O1B C1B C2B C3B -173.5(5) . . . . ? O2B C1B C2B C3B 3.1(8) . . . . ? C2Y C1B C2B C3B 96.5(16) . . . . ? C1B C2B C3B C4B -174.3(6) . . . . ? C2B C3B C4B C5B 8.5(9) . . . . ? C2B C3B C4B C9B -171.9(6) . . . . ? C9B C4B C5B C6B -0.9(9) . . . . ? C3B C4B C5B C6B 178.6(6) . . . . ? C4B C5B C6B C7B -0.7(10) . . . . ? C5B C6B C7B C8B 1.6(9) . . . . ? C5B C6B C7B S1B -173.5(5) . . . . ? O6B S1B C7B C8B 33.1(6) . . . . ? O5B S1B C7B C8B 163.0(5) . . . . ? N1B S1B C7B C8B -80.5(6) . . . . ? C7Y S1B C7B C8B -126(4) . . . . ? O6B S1B C7B C6B -151.9(5) . . . . ? O5B S1B C7B C6B -22.0(5) . . . . ? N1B S1B C7B C6B 94.6(5) . . . . ? C7Y S1B C7B C6B 49(4) . . . . ? C6B C7B C8B C9B -0.8(11) . . . . ? S1B C7B C8B C9B 174.2(6) . . . . ? C7B C8B C9B C4B -0.8(11) . . . . ? C5B C4B C9B C8B 1.7(10) . . . . ? C3B C4B C9B C8B -177.9(7) . . . . ? S1B N1B C11B C10B 80.1(4) . . . . ? S1B N1B C11B C12B -160.9(3) . . . . ? O4B C10B C11B N1B 35.9(6) . . . . ? O3B C10B C11B N1B -144.7(4) . . . . ? O4B C10B C11B C12B -85.1(6) . . . . ? O3B C10B C11B C12B 94.3(5) . . . . ? N1B C11B C12B C13B 60.4(6) . . . . ? C10B C11B C12B C13B -176.5(4) . . . . ? C11B C12B C13B C14B 70.9(6) . . . . ? C11B C12B C13B C18B -110.8(6) . . . . ? C18B C13B C14B C15B -0.4(9) . . . . ? C12B C13B C14B C15B 178.0(5) . . . . ? C13B C14B C15B C16B 2.9(10) . . . . ? C14B C15B C16B C17B -4.0(11) . . . . ? C15B C16B C17B C18B 2.5(11) . . . . ? C14B C13B C18B C17B -1.1(9) . . . . ? C12B C13B C18B C17B -179.4(6) . . . . ? C16B C17B C18B C13B 0.1(10) . . . . ? O2A C1A C2X C3X -29(3) . . . . ? O1A C1A C2X C3X -175(2) . . . . ? C2A C1A C2X C3X 70(2) . . . . ? O2A C1A C2X C3Y 76(2) . . . . ? O1A C1A C2X C3Y -69.0(19) . . . . ? C2A C1A C2X C3Y 176(3) . . . . ? C1A C2X C3X C4X -117(2) . . . . ? C3Y C2X C3X C4X 123(2) . . . . ? C1A C2X C3X C2Y 119(2) . . . . ? C3Y C2X C3X C2Y -1(2) . . . . ? C2X C3X C4X C9X 173(2) . . . . ? C2Y C3X C4X C9X -79(3) . . . . ? C2X C3X C4X C5X -24(4) . . . . ? C2Y C3X C4X C5X 84(3) . . . . ? C9X C4X C5X C6X -1(2) . . . . ? C3X C4X C5X C6X -164(3) . . . . ? C4X C5X C6X C7X 2(2) . . . . ? C5X C6X C7X C8X -8(5) . . . . ? C5X C6X C7X S1A 179(2) . . . . ? O6A S1A C7X C8X 4(4) . . . . ? O5A S1A C7X C8X -132(3) . . . . ? N1A S1A C7X C8X 116(3) . . . . ? C7A S1A C7X C8X -94(7) . . . . ? O6A S1A C7X C6X 177(2) . . . . ? O5A S1A C7X C6X 40(3) . . . . ? N1A S1A C7X C6X -71(3) . . . . ? C7A S1A C7X C6X 79(6) . . . . ? C6X C7X C8X C9X 12(6) . . . . ? S1A C7X C8X C9X -176(3) . . . . ? C7X C8X C9X C4X -11(6) . . . . ? C5X C4X C9X C8X 6(4) . . . . ? C3X C4X C9X C8X 169(3) . . . . ? O1B C1B C2Y C3Y 179.6(18) . . . . ? O2B C1B C2Y C3Y 36(3) . . . . ? C2B C1B C2Y C3Y -69(2) . . . . ? O1B C1B C2Y C3X 80.4(19) . . . . ? O2B C1B C2Y C3X -64(2) . . . . ? C2B C1B C2Y C3X -169(3) . . . . ? C2X C3X C2Y C1B 117(2) . . . . ? C4X C3X C2Y C1B -6(3) . . . . ? C2X C3X C2Y C3Y 1(2) . . . . ? C4X C3X C2Y C3Y -121(2) . . . . ? C1B C2Y C3Y C2X -118(2) . . . . ? C3X C2Y C3Y C2X -1(2) . . . . ? C1B C2Y C3Y C4Y 121(2) . . . . ? C3X C2Y C3Y C4Y -122(2) . . . . ? C1A C2X C3Y C2Y -118(2) . . . . ? C3X C2X C3Y C2Y 2(2) . . . . ? C1A C2X C3Y C4Y -1(3) . . . . ? C3X C2X C3Y C4Y 119(2) . . . . ? C2Y C3Y C4Y C5Y 39(4) . . . . ? C2X C3Y C4Y C5Y -66(4) . . . . ? C2Y C3Y C4Y C9Y -153(3) . . . . ? C2X C3Y C4Y C9Y 103(3) . . . . ? C9Y C4Y C5Y C6Y -3(5) . . . . ? C3Y C4Y C5Y C6Y 165(3) . . . . ? C4Y C5Y C6Y C7Y 0(5) . . . . ? C5Y C6Y C7Y C8Y 0(5) . . . . ? C5Y C6Y C7Y S1B -178(3) . . . . ? O6B S1B C7Y C8Y 24(3) . . . . ? O5B S1B C7Y C8Y 161(3) . . . . ? N1B S1B C7Y C8Y -89(3) . . . . ? C7B S1B C7Y C8Y 47(4) . . . . ? O6B S1B C7Y C6Y -158(3) . . . . ? O5B S1B C7Y C6Y -21(3) . . . . ? N1B S1B C7Y C6Y 89(3) . . . . ? C7B S1B C7Y C6Y -135(7) . . . . ? C6Y C7Y C8Y C9Y 2(6) . . . . ? S1B C7Y C8Y C9Y -180(3) . . . . ? C7Y C8Y C9Y C4Y -5(6) . . . . ? C5Y C4Y C9Y C8Y 6(5) . . . . ? C3Y C4Y C9Y C8Y -163(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1 O4B 0.85(2) 1.80(2) 2.637(4) 169(6) . O3B H4 O2A 0.84(2) 1.83(2) 2.667(4) 176(5) . O2B H3 O3A 0.866(19) 1.79(2) 2.659(4) 176(2) . O4A H2 O1B 0.85(2) 1.81(2) 2.656(4) 169(5) . N1B H6 O1B 0.840(19) 2.18(2) 3.017(5) 173(5) 1_655 N1A H5 O5B 0.808(19) 2.18(2) 2.971(4) 166(5) 1_454 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 67.34 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.545 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.063 data_kaw121 _database_code_depnum_ccdc_archive 'CCDC 895733' #TrackingRef '- wheeler-ChemComm13.CIF' # (rac)-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 N O7 S, C3 H6 O' _chemical_formula_sum 'C21 H23 N O8 S' _chemical_formula_weight 449.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6186(3) _cell_length_b 11.3663(4) _cell_length_c 11.7792(6) _cell_angle_alpha 61.273(2) _cell_angle_beta 76.368(3) _cell_angle_gamma 67.977(2) _cell_volume 1044.45(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8032 _cell_measurement_theta_min 4.100 _cell_measurement_theta_max 70.511 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 1.815 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4750 _exptl_absorpt_correction_T_max 0.8049 _exptl_absorpt_process_details 'SADABS (Bruker, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 19333 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.29 _diffrn_reflns_theta_max 67.54 _reflns_number_total 3626 _reflns_number_gt 2647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2008) and XPREP (Bruker, 2008) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _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. All non-hydrogen atoms were located in a difference Fourier map and refined using anisotropic displacement parameters. The hydrogen atoms were placed in fixed positions with Ueq = 1.2xUiso of the carbon atom to which they are attached (Ueq = 1.5xUiso for methyl groups). NH and OH hydrogen atoms were located in diff maps and refined N/O-H distances of 0.84(2) angstroms and with Ueq = 1.2xUiso of the corresponding N/O atoms. A portion of the sulfonamide group (O5, O6, N1, C11) shows disorder in a 85:15 ratio. Both the major and minor components were refined with isotropic displacement parameters. The minor component was restrained with DELU and ISOR commands. ; _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^)+(0.0408P)^2^+1.7431P] 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 3626 _refine_ls_number_parameters 335 _refine_ls_number_restraints 55 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1622 _refine_ls_wR_factor_gt 0.1488 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.148 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.004 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 -0.09191(8) 0.75515(8) 0.38932(7) 0.03382(19) Uani 1 1 d U . . O1 O 0.4424(2) 1.3041(2) -0.2744(2) 0.0439(6) Uani 1 1 d D . . H22 H 0.509(3) 1.328(3) -0.333(2) 0.053 Uiso 1 1 d D . . O2 O 0.5293(3) 1.0922(2) -0.2738(2) 0.0446(6) Uani 1 1 d . . . O3 O 0.2394(3) 0.8703(3) 0.4383(2) 0.0503(7) Uani 1 1 d D A . H23 H 0.317(2) 0.885(4) 0.389(3) 0.060 Uiso 1 1 d D . . O4 O 0.3206(3) 0.6550(2) 0.4474(2) 0.0492(6) Uani 1 1 d . A . O5 O -0.2056(3) 0.8634(3) 0.4114(3) 0.0381(8) Uani 0.858(3) 1 d PU A 1 O6 O -0.1293(3) 0.6504(3) 0.3741(2) 0.0355(7) Uani 0.858(3) 1 d PU A 1 O7 O -0.4118(3) 0.5927(3) 1.0365(2) 0.0488(7) Uani 1 1 d D A . H10 H -0.404(4) 0.5079(19) 1.086(3) 0.059 Uiso 1 1 d D . . O8 O -0.3934(3) 0.3179(3) 1.1975(2) 0.0518(7) Uani 1 1 d . . . N1 N 0.0118(3) 0.6625(3) 0.5128(3) 0.0306(7) Uani 0.858(3) 1 d PDU A 1 H24 H 0.056(4) 0.5785(18) 0.527(3) 0.037 Uiso 0.858(3) 1 d PD A 1 C1 C 0.4432(3) 1.1741(3) -0.2304(3) 0.0345(8) Uani 1 1 d . . . C2 C 0.3307(3) 1.1348(3) -0.1231(3) 0.0354(8) Uani 1 1 d . . . H2 H 0.2684 1.2009 -0.0931 0.042 Uiso 1 1 calc R . . C3 C 0.3157(3) 1.0070(3) -0.0678(3) 0.0352(8) Uani 1 1 d . . . H3 H 0.3784 0.9457 -0.1029 0.042 Uiso 1 1 calc R . . C4 C 0.2123(3) 0.9507(3) 0.0419(3) 0.0315(7) Uani 1 1 d . . . C5 C 0.2270(3) 0.8073(3) 0.0958(3) 0.0376(8) Uani 1 1 d . A . H5 H 0.3017 0.7504 0.0614 0.045 Uiso 1 1 calc R . . C6 C 0.1322(3) 0.7485(3) 0.1993(3) 0.0360(8) Uani 1 1 d . . . H6 H 0.1427 0.6530 0.2343 0.043 Uiso 1 1 calc R A . C7 C 0.0217(3) 0.8340(3) 0.2497(3) 0.0308(7) Uani 1 1 d . A . C8 C 0.0026(3) 0.9767(3) 0.1983(3) 0.0341(7) Uani 1 1 d . . . H8 H -0.0724 1.0330 0.2331 0.041 Uiso 1 1 calc R A . C9 C 0.0978(3) 1.0339(3) 0.0936(3) 0.0345(8) Uani 1 1 d . A . H9 H 0.0847 1.1300 0.0572 0.041 Uiso 1 1 calc R . . C10 C 0.2268(4) 0.7487(4) 0.4720(3) 0.0400(8) Uani 1 1 d U . . C11 C 0.0792(4) 0.7321(4) 0.5515(3) 0.0300(9) Uani 0.858(3) 1 d PU A 1 H11 H 0.0091 0.8256 0.5378 0.036 Uiso 0.858(3) 1 calc PR A 1 C12 C 0.1111(3) 0.6459(4) 0.6961(3) 0.0380(8) Uani 1 1 d . . . H12A H 0.1803 0.5531 0.7098 0.046 Uiso 1 1 calc R A 1 H12B H 0.1594 0.6919 0.7190 0.046 Uiso 1 1 calc R A 1 C13 C -0.0294(3) 0.6295(3) 0.7844(3) 0.0332(7) Uani 1 1 d . A . C14 C -0.0482(3) 0.4984(3) 0.8635(3) 0.0356(8) Uani 1 1 d . . . H14 H 0.0251 0.4189 0.8592 0.043 Uiso 1 1 calc R A . C15 C -0.1739(4) 0.4826(3) 0.9489(3) 0.0370(8) Uani 1 1 d . A . H15 H -0.1837 0.3933 1.0025 0.044 Uiso 1 1 calc R . . C16 C -0.2848(3) 0.6010(3) 0.9540(3) 0.0351(8) Uani 1 1 d . . . C17 C -0.2690(4) 0.7331(3) 0.8738(3) 0.0404(8) Uani 1 1 d . A . H17 H -0.3435 0.8129 0.8762 0.048 Uiso 1 1 calc R . . C18 C -0.1420(4) 0.7461(3) 0.7899(3) 0.0366(8) Uani 1 1 d . . . H18 H -0.1323 0.8354 0.7361 0.044 Uiso 1 1 calc R A . C19 C -0.4903(4) 0.1464(4) 1.3725(4) 0.0503(10) Uani 1 1 d . . . H19A H -0.4213 0.0856 1.3352 0.075 Uiso 1 1 calc R . . H19B H -0.5902 0.1433 1.3782 0.075 Uiso 1 1 calc R . . H19C H -0.4623 0.1155 1.4578 0.075 Uiso 1 1 calc R . . C20 C -0.4858(3) 0.2928(4) 1.2897(3) 0.0391(8) Uani 1 1 d . . . C21 C -0.5966(4) 0.4032(4) 1.3254(4) 0.0506(10) Uani 1 1 d . . . H21A H -0.5840 0.4933 1.2650 0.076 Uiso 1 1 calc R . . H21B H -0.5815 0.3835 1.4113 0.076 Uiso 1 1 calc R . . H21C H -0.6964 0.4046 1.3232 0.076 Uiso 1 1 calc R . . O5A O -0.2405(19) 0.878(2) 0.3732(17) 0.038(5) Uani 0.142(3) 1 d PU A 2 O6A O -0.0815(17) 0.6410(15) 0.4076(15) 0.0259(17) Uani 0.142(3) 1 d PU A 2 N1A N -0.0330(19) 0.7710(15) 0.5055(17) 0.033(3) Uani 0.142(3) 1 d PDU A 2 C11A C 0.100(3) 0.675(2) 0.557(2) 0.028(4) Uani 0.142(3) 1 d PU A 2 H11A H 0.1189 0.5867 0.5516 0.034 Uiso 0.142(3) 1 calc PR A 2 H25 H -0.048(12) 0.850(4) 0.503(9) 0.00(4) Uiso 0.142(3) 1 d PD A 2 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 0.0245(3) 0.0440(4) 0.0269(3) -0.0115(3) 0.0015(3) -0.0114(3) O1 0.0392(11) 0.0455(11) 0.0431(12) -0.0182(10) 0.0105(10) -0.0184(10) O2 0.0423(12) 0.0418(11) 0.0452(12) -0.0194(10) 0.0137(10) -0.0178(10) O3 0.0434(12) 0.0543(13) 0.0462(13) -0.0189(11) 0.0139(11) -0.0222(11) O4 0.0452(12) 0.0545(12) 0.0477(13) -0.0207(11) 0.0097(11) -0.0250(11) O5 0.0285(13) 0.0420(13) 0.0318(14) -0.0124(11) 0.0020(11) -0.0056(11) O6 0.0319(12) 0.0411(12) 0.0318(13) -0.0113(10) -0.0014(10) -0.0161(10) O7 0.0380(12) 0.0566(13) 0.0384(12) -0.0187(11) 0.0126(10) -0.0126(11) O8 0.0371(12) 0.0621(14) 0.0452(13) -0.0168(11) 0.0087(11) -0.0198(11) N1 0.0279(13) 0.0307(13) 0.0280(14) -0.0092(11) -0.0019(11) -0.0084(11) C1 0.0281(14) 0.0427(16) 0.0286(15) -0.0120(13) -0.0029(12) -0.0109(13) C2 0.0290(14) 0.0403(15) 0.0304(15) -0.0135(13) 0.0001(12) -0.0078(13) C3 0.0277(14) 0.0449(16) 0.0301(15) -0.0184(13) 0.0017(12) -0.0075(13) C4 0.0253(13) 0.0388(14) 0.0267(14) -0.0118(12) -0.0028(11) -0.0087(12) C5 0.0307(15) 0.0376(15) 0.0337(16) -0.0147(13) 0.0036(13) -0.0040(13) C6 0.0312(15) 0.0329(14) 0.0324(16) -0.0101(13) 0.0010(13) -0.0055(13) C7 0.0262(13) 0.0414(14) 0.0229(13) -0.0135(12) -0.0005(11) -0.0098(12) C8 0.0313(14) 0.0389(14) 0.0354(15) -0.0208(12) 0.0056(12) -0.0127(12) C9 0.0355(15) 0.0307(13) 0.0344(15) -0.0121(12) -0.0017(13) -0.0102(13) C10 0.0344(15) 0.0568(18) 0.0310(15) -0.0195(14) 0.0000(13) -0.0170(15) C11 0.0297(16) 0.0335(17) 0.0248(16) -0.0117(14) 0.0015(13) -0.0111(15) C12 0.0319(15) 0.0488(16) 0.0296(15) -0.0134(13) -0.0018(13) -0.0135(14) C13 0.0314(14) 0.0425(15) 0.0238(14) -0.0134(12) -0.0010(12) -0.0114(13) C14 0.0323(15) 0.0359(15) 0.0313(15) -0.0131(12) -0.0018(13) -0.0053(13) C15 0.0423(16) 0.0411(15) 0.0255(15) -0.0104(12) -0.0007(13) -0.0170(14) C16 0.0304(14) 0.0462(15) 0.0268(14) -0.0163(12) 0.0009(12) -0.0110(13) C17 0.0383(16) 0.0436(16) 0.0338(16) -0.0187(13) 0.0003(14) -0.0062(14) C18 0.0437(17) 0.0354(14) 0.0297(15) -0.0126(12) -0.0008(13) -0.0144(14) C19 0.0409(18) 0.0470(18) 0.050(2) -0.0167(16) 0.0013(16) -0.0084(16) C20 0.0302(15) 0.0494(17) 0.0330(16) -0.0141(14) -0.0056(13) -0.0106(14) C21 0.050(2) 0.0449(18) 0.046(2) -0.0164(16) 0.0003(17) -0.0100(16) O5A 0.025(6) 0.047(6) 0.026(8) -0.011(6) 0.003(5) -0.003(5) O6A 0.026(2) 0.025(2) 0.026(2) -0.0100(14) -0.0021(16) -0.0087(15) N1A 0.035(5) 0.029(5) 0.039(6) -0.009(4) -0.004(5) -0.020(5) C11A 0.031(6) 0.025(7) 0.034(7) -0.016(5) -0.004(5) -0.010(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 S1 O6A 1.177(16) . ? S1 O5 1.393(3) . ? S1 O6 1.461(3) . ? S1 O5A 1.549(17) . ? S1 N1 1.626(3) . ? S1 N1A 1.704(19) . ? S1 C7 1.781(3) . ? O1 C1 1.307(4) . ? O1 H22 0.834(17) . ? O2 C1 1.222(4) . ? O3 C10 1.288(4) . ? O3 H23 0.847(17) . ? O4 C10 1.219(4) . ? O7 C16 1.373(4) . ? O7 H10 0.839(16) . ? O8 C20 1.219(4) . ? N1 C11 1.457(5) . ? N1 H24 0.836(16) . ? C1 C2 1.464(4) . ? C2 C3 1.327(5) . ? C2 H2 0.9300 . ? C3 C4 1.464(4) . ? C3 H3 0.9300 . ? C4 C9 1.392(4) . ? C4 C5 1.398(4) . ? C5 C6 1.383(4) . ? C5 H5 0.9300 . ? C6 C7 1.382(4) . ? C6 H6 0.9300 . ? C7 C8 1.384(4) . ? C8 C9 1.387(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.527(5) . ? C10 C11A 1.61(2) . ? C11 C12 1.540(5) . ? C11 H11 0.9800 . ? C12 C13 1.510(4) . ? C12 C11A 1.53(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.381(4) . ? C13 C14 1.382(4) . ? C14 C15 1.386(4) . ? C14 H14 0.9300 . ? C15 C16 1.387(4) . ? C15 H15 0.9300 . ? C16 C17 1.382(5) . ? C17 C18 1.385(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.482(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.478(5) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N1A C11A 1.37(3) . ? N1A H25 0.84(2) . ? C11A H11A 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 O5 S1 O6 120.30(17) . . ? O5 S1 N1 108.03(17) . . ? O6 S1 N1 104.04(15) . . ? O6A S1 N1A 117.5(9) . . ? O5A S1 N1A 94.5(10) . . ? O6A S1 C7 111.6(8) . . ? O5 S1 C7 107.65(16) . . ? O6 S1 C7 108.29(15) . . ? O5A S1 C7 102.3(7) . . ? N1 S1 C7 107.99(14) . . ? N1A S1 C7 101.9(6) . . ? C1 O1 H22 115(3) . . ? C10 O3 H23 114(3) . . ? C16 O7 H10 109(3) . . ? C11 N1 S1 119.6(2) . . ? C11 N1 H24 119(3) . . ? S1 N1 H24 115(3) . . ? O2 C1 O1 123.7(3) . . ? O2 C1 C2 122.7(3) . . ? O1 C1 C2 113.6(3) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 127.9(3) . . ? C2 C3 H3 116.1 . . ? C4 C3 H3 116.1 . . ? C9 C4 C5 118.2(3) . . ? C9 C4 C3 123.0(3) . . ? C5 C4 C3 118.7(3) . . ? C6 C5 C4 121.2(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C7 C6 C5 118.9(3) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C8 121.7(3) . . ? C6 C7 S1 118.5(2) . . ? C8 C7 S1 119.8(2) . . ? C7 C8 C9 118.5(3) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C8 C9 C4 121.5(3) . . ? C8 C9 H9 119.3 . . ? C4 C9 H9 119.3 . . ? O4 C10 O3 125.4(3) . . ? O4 C10 C11 122.7(3) . . ? O3 C10 C11 111.9(3) . . ? O4 C10 C11A 101.6(9) . . ? N1 C11 C10 111.2(3) . . ? N1 C11 C12 110.3(3) . . ? C10 C11 C12 108.5(3) . . ? N1 C11 H11 108.9 . . ? C10 C11 H11 108.9 . . ? C12 C11 H11 108.9 . . ? C10 C11 H25 115(4) . . ? C12 C11 H25 124(4) . . ? C13 C12 C11A 114.9(10) . . ? C13 C12 C11 112.9(3) . . ? C13 C12 H12A 109.0 . . ? C11A C12 H12A 88.6 . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C11A C12 H12B 124.4 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C18 C13 C14 118.0(3) . . ? C18 C13 C12 120.5(3) . . ? C14 C13 C12 121.5(3) . . ? C13 C14 C15 121.5(3) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C14 C15 C16 119.5(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? O7 C16 C17 117.9(3) . . ? O7 C16 C15 122.4(3) . . ? C17 C16 C15 119.7(3) . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C13 C18 C17 121.5(3) . . ? C13 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 C20 C21 122.8(3) . . ? O8 C20 C19 120.4(3) . . ? C21 C20 C19 116.7(3) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C11A N1A S1 116.5(16) . . ? C11A N1A H25 113(7) . . ? S1 N1A H25 122(6) . . ? N1A C11A C12 113.7(18) . . ? N1A C11A C10 105.2(15) . . ? C12 C11A C10 105.1(16) . . ? C12 C11A H24 122(2) . . ? C10 C11A H24 123(2) . . ? N1A C11A H11A 110.8 . . ? C12 C11A H11A 110.8 . . ? C10 C11A H11A 110.8 . . ? 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 O6A S1 N1 C11 170.6(8) . . . . ? O5 S1 N1 C11 -55.2(3) . . . . ? O6 S1 N1 C11 175.9(3) . . . . ? O5A S1 N1 C11 -61.6(10) . . . . ? N1A S1 N1 C11 -25.7(9) . . . . ? C7 S1 N1 C11 60.9(3) . . . . ? O2 C1 C2 C3 -0.6(5) . . . . ? O1 C1 C2 C3 179.5(3) . . . . ? C1 C2 C3 C4 178.1(3) . . . . ? C2 C3 C4 C9 9.1(5) . . . . ? C2 C3 C4 C5 -172.3(3) . . . . ? C9 C4 C5 C6 -1.2(5) . . . . ? C3 C4 C5 C6 -179.9(3) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? C5 C6 C7 C8 0.8(5) . . . . ? C5 C6 C7 S1 -176.1(3) . . . . ? O6A S1 C7 C6 -15.5(9) . . . . ? O5 S1 C7 C6 -172.6(3) . . . . ? O6 S1 C7 C6 -41.1(3) . . . . ? O5A S1 C7 C6 -152.0(9) . . . . ? N1 S1 C7 C6 71.0(3) . . . . ? N1A S1 C7 C6 110.7(6) . . . . ? O6A S1 C7 C8 167.5(9) . . . . ? O5 S1 C7 C8 10.4(3) . . . . ? O6 S1 C7 C8 141.9(3) . . . . ? O5A S1 C7 C8 31.1(9) . . . . ? N1 S1 C7 C8 -106.0(3) . . . . ? N1A S1 C7 C8 -66.3(6) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? S1 C7 C8 C9 176.7(3) . . . . ? C7 C8 C9 C4 -1.2(5) . . . . ? C5 C4 C9 C8 1.9(5) . . . . ? C3 C4 C9 C8 -179.5(3) . . . . ? S1 N1 C11 C10 -84.2(3) . . . . ? S1 N1 C11 C12 155.4(2) . . . . ? O4 C10 C11 N1 -43.0(4) . . . . ? O3 C10 C11 N1 138.4(3) . . . . ? C11A C10 C11 N1 -45(3) . . . . ? O4 C10 C11 C12 78.5(4) . . . . ? O3 C10 C11 C12 -100.1(3) . . . . ? C11A C10 C11 C12 76(3) . . . . ? N1 C11 C12 C13 -60.9(4) . . . . ? C10 C11 C12 C13 177.0(3) . . . . ? N1 C11 C12 C11A 39(3) . . . . ? C10 C11 C12 C11A -83(3) . . . . ? C11A C12 C13 C18 -86.8(10) . . . . ? C11 C12 C13 C18 -63.0(4) . . . . ? C11A C12 C13 C14 94.4(10) . . . . ? C11 C12 C13 C14 118.2(4) . . . . ? C18 C13 C14 C15 -1.8(5) . . . . ? C12 C13 C14 C15 177.0(3) . . . . ? C13 C14 C15 C16 1.1(5) . . . . ? C14 C15 C16 O7 -179.9(3) . . . . ? C14 C15 C16 C17 0.1(5) . . . . ? O7 C16 C17 C18 179.4(3) . . . . ? C15 C16 C17 C18 -0.6(5) . . . . ? C14 C13 C18 C17 1.4(5) . . . . ? C12 C13 C18 C17 -177.5(3) . . . . ? C16 C17 C18 C13 -0.2(5) . . . . ? O6A S1 N1A C11A 43.2(19) . . . . ? O5 S1 N1A C11A 175.9(16) . . . . ? O6 S1 N1A C11A 58.0(19) . . . . ? O5A S1 N1A C11A 177.4(16) . . . . ? N1 S1 N1A C11A 25.0(12) . . . . ? C7 S1 N1A C11A -79.0(15) . . . . ? S1 N1A C11A C12 -152.2(13) . . . . ? S1 N1A C11A C10 93.2(17) . . . . ? C13 C12 C11A N1A 43(2) . . . . ? C11 C12 C11A N1A -46.7(19) . . . . ? C13 C12 C11A C10 157.5(8) . . . . ? C11 C12 C11A C10 68(2) . . . . ? O4 C10 C11A N1A -131.9(15) . . . . ? O3 C10 C11A N1A 51(2) . . . . ? C11 C10 C11A N1A 46.2(19) . . . . ? O4 C10 C11A C12 107.8(11) . . . . ? O3 C10 C11A C12 -69.5(15) . . . . ? C11 C10 C11A C12 -74(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H10 O8 0.839(16) 1.888(17) 2.726(3) 178(4) . O3 H23 O2 0.847(17) 1.760(18) 2.602(3) 172(4) 2_675 O1 H22 O4 0.834(17) 1.871(18) 2.695(3) 169(3) 2_675 N1 H24 O6 0.836(16) 2.173(17) 2.973(4) 161(3) 2_566 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 67.54 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.542 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.084 data_kaw144 _database_code_depnum_ccdc_archive 'CCDC 895734' #TrackingRef '- wheeler-ChemComm13.CIF' # (rac)-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N O6 S' _chemical_formula_sum 'C19 H19 N O6 S' _chemical_formula_weight 389.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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' _symmetry_space_group_name_Hall '-P 2yn' 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 9.6628(1) _cell_length_b 12.9705(2) _cell_length_c 15.2675(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.034(1) _cell_angle_gamma 90.00 _cell_volume 1819.49(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8132 _cell_measurement_theta_min 3.407 _cell_measurement_theta_max 66.891 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 1.910 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6335 _exptl_absorpt_correction_T_max 0.8469 _exptl_absorpt_process_details 'SADABS (Bruker, 2010)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 25034 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.57 _diffrn_reflns_theta_max 67.80 _reflns_number_total 3271 _reflns_number_gt 2672 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2008) and XPREP (Bruker, 2008) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSEED (Barbour, 2001)' _computing_publication_material 'XSEED (Barbour, 2001)' _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. All non-hydrogen atoms were located in a single difference Fourier map and refined with anisotropic thermal parameters. The N-H and O-H hydrogen atoms were located in difference density Fourier maps and refined with O/N-H distances of 0.84(2) angstroms and Uiso = 1.2Ueq of the corresponding O/N atoms. All other H atoms were place in calculated positions and refined with Uiso = 1.2Ueq of the corresponding C atom (Uiso = 1.5eq for methyl C-H groups). ; _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^)+(0.0548P)^2^+0.7995P] 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 3271 _refine_ls_number_parameters 254 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.037 _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 0.77149(5) 0.14635(4) 0.00085(3) 0.02790(15) Uani 1 1 d . . . O1 O -0.05730(16) 0.30879(12) -0.38753(11) 0.0415(4) Uani 1 1 d D . . H20 H -0.145(2) 0.3300(19) -0.4208(16) 0.050 Uiso 1 1 d D . . O2 O -0.10517(15) 0.17308(12) -0.48353(10) 0.0396(4) Uani 1 1 d . . . O3 O 1.14095(16) 0.25862(12) -0.08184(10) 0.0362(4) Uani 1 1 d D . . H21 H 1.217(2) 0.2774(19) -0.0451(15) 0.043 Uiso 1 1 d D . . O4 O 1.17271(14) 0.13582(11) 0.02508(9) 0.0323(3) Uani 1 1 d . . . O5 O 0.83671(16) 0.24465(11) 0.02918(10) 0.0390(4) Uani 1 1 d . . . O6 O 0.74080(15) 0.07721(12) 0.06541(9) 0.0352(3) Uani 1 1 d . . . N1 N 0.87941(17) 0.08562(13) -0.04361(11) 0.0265(4) Uani 1 1 d D . . H22 H 0.867(2) 0.0235(13) -0.0497(15) 0.032 Uiso 1 1 d D . . C1 C -0.0247(2) 0.21843(17) -0.41590(15) 0.0347(5) Uani 1 1 d . . . C2 C 0.1159(2) 0.17312(17) -0.35845(15) 0.0350(5) Uani 1 1 d . . . C3 C 0.2027(2) 0.23144(17) -0.29265(15) 0.0350(5) Uani 1 1 d . . . H3 H 0.1690 0.2995 -0.2884 0.042 Uiso 1 1 calc R . . C4 C 0.1442(3) 0.0664(2) -0.38591(17) 0.0472(6) Uani 1 1 d . . . H4A H 0.2449 0.0469 -0.3529 0.071 Uiso 1 1 calc R . . H4B H 0.1289 0.0643 -0.4524 0.071 Uiso 1 1 calc R . . H4C H 0.0775 0.0180 -0.3704 0.071 Uiso 1 1 calc R . . C5 C 0.3447(2) 0.20506(16) -0.22511(14) 0.0328(5) Uani 1 1 d . . . C6 C 0.4507(2) 0.28145(17) -0.20030(15) 0.0343(5) Uani 1 1 d . . . H6 H 0.4329 0.3465 -0.2303 0.041 Uiso 1 1 calc R . . C7 C 0.5821(2) 0.26383(16) -0.13225(15) 0.0342(5) Uani 1 1 d . . . H7 H 0.6544 0.3162 -0.1160 0.041 Uiso 1 1 calc R . . C8 C 0.6068(2) 0.16914(16) -0.08826(14) 0.0304(4) Uani 1 1 d . . . C9 C 0.5018(2) 0.09156(16) -0.11206(15) 0.0345(5) Uani 1 1 d . . . H9 H 0.5197 0.0267 -0.0817 0.041 Uiso 1 1 calc R . . C10 C 0.3715(2) 0.10981(17) -0.18020(15) 0.0360(5) Uani 1 1 d . . . H10 H 0.2996 0.0572 -0.1966 0.043 Uiso 1 1 calc R . . C11 C 1.0992(2) 0.17883(15) -0.04524(14) 0.0289(4) Uani 1 1 d . . . C12 C 0.9489(2) 0.14090(16) -0.10147(13) 0.0291(4) Uani 1 1 d . . . H12 H 0.8876 0.2020 -0.1287 0.035 Uiso 1 1 calc R . . C13 C 0.9626(2) 0.07232(17) -0.18014(14) 0.0331(5) Uani 1 1 d . . . H13A H 1.0191 0.1092 -0.2145 0.040 Uiso 1 1 calc R . . H13B H 1.0164 0.0088 -0.1541 0.040 Uiso 1 1 calc R . . C14 C 0.8152(2) 0.04356(17) -0.24558(13) 0.0320(5) Uani 1 1 d . . . C15 C 0.7326(2) 0.11509(19) -0.30750(15) 0.0407(5) Uani 1 1 d . . . H15 H 0.7695 0.1827 -0.3091 0.049 Uiso 1 1 calc R . . C16 C 0.5971(3) 0.0891(2) -0.36712(16) 0.0466(6) Uani 1 1 d . . . H16 H 0.5422 0.1384 -0.4099 0.056 Uiso 1 1 calc R . . C17 C 0.5415(2) -0.0089(2) -0.36425(16) 0.0441(6) Uani 1 1 d . . . H17 H 0.4492 -0.0274 -0.4056 0.053 Uiso 1 1 calc R . . C18 C 0.6212(2) -0.07934(18) -0.30084(15) 0.0423(5) Uani 1 1 d . . . H18 H 0.5823 -0.1459 -0.2971 0.051 Uiso 1 1 calc R . . C19 C 0.7574(2) -0.05350(18) -0.24279(15) 0.0368(5) Uani 1 1 d . . . H19 H 0.8122 -0.1031 -0.2003 0.044 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 0.0223(2) 0.0336(3) 0.0274(2) -0.0007(2) 0.00706(18) 0.00155(19) O1 0.0282(8) 0.0408(9) 0.0498(10) 0.0005(7) 0.0036(7) 0.0065(7) O2 0.0304(8) 0.0481(9) 0.0370(8) -0.0002(7) 0.0058(7) 0.0043(7) O3 0.0275(7) 0.0401(9) 0.0368(8) 0.0075(7) 0.0040(6) -0.0055(6) O4 0.0237(7) 0.0342(8) 0.0347(8) 0.0046(6) 0.0026(6) -0.0013(6) O5 0.0341(8) 0.0395(8) 0.0419(9) -0.0093(7) 0.0096(7) -0.0026(7) O6 0.0283(7) 0.0468(9) 0.0319(7) 0.0066(6) 0.0114(6) 0.0042(6) N1 0.0215(8) 0.0284(9) 0.0296(8) 0.0015(7) 0.0077(6) 0.0009(7) C1 0.0279(10) 0.0416(12) 0.0363(12) 0.0065(9) 0.0124(9) 0.0019(9) C2 0.0285(10) 0.0403(12) 0.0386(12) 0.0077(9) 0.0141(9) 0.0044(9) C3 0.0265(10) 0.0415(12) 0.0393(12) 0.0096(10) 0.0136(9) 0.0049(9) C4 0.0386(12) 0.0531(15) 0.0447(13) -0.0002(11) 0.0051(10) 0.0111(11) C5 0.0286(10) 0.0367(11) 0.0348(11) 0.0048(9) 0.0123(9) 0.0039(9) C6 0.0312(11) 0.0349(11) 0.0386(11) 0.0050(9) 0.0134(9) 0.0034(9) C7 0.0286(10) 0.0351(11) 0.0402(12) 0.0016(9) 0.0125(9) 0.0002(9) C8 0.0230(9) 0.0373(11) 0.0325(10) 0.0019(9) 0.0107(8) 0.0061(8) C9 0.0264(10) 0.0361(12) 0.0394(12) 0.0061(9) 0.0081(9) 0.0028(9) C10 0.0257(10) 0.0392(12) 0.0416(12) 0.0041(10) 0.0083(9) -0.0010(9) C11 0.0248(10) 0.0310(11) 0.0327(11) -0.0008(8) 0.0115(8) 0.0015(8) C12 0.0228(9) 0.0351(11) 0.0291(10) 0.0030(8) 0.0078(8) 0.0017(8) C13 0.0273(10) 0.0427(12) 0.0295(10) 0.0021(9) 0.0089(8) 0.0038(9) C14 0.0270(10) 0.0444(12) 0.0251(10) -0.0017(9) 0.0088(8) 0.0034(9) C15 0.0379(12) 0.0448(13) 0.0377(12) 0.0060(10) 0.0092(10) 0.0009(10) C16 0.0381(12) 0.0603(16) 0.0365(12) 0.0085(11) 0.0044(10) 0.0157(12) C17 0.0308(11) 0.0583(15) 0.0386(12) -0.0110(11) 0.0041(9) 0.0015(11) C18 0.0417(13) 0.0420(13) 0.0411(12) -0.0113(10) 0.0096(10) -0.0022(10) C19 0.0370(11) 0.0393(12) 0.0321(11) -0.0025(9) 0.0077(9) 0.0055(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 S1 O5 1.4286(15) . ? S1 O6 1.4299(15) . ? S1 N1 1.6146(16) . ? S1 C8 1.769(2) . ? O1 C1 1.321(3) . ? O1 H20 0.886(17) . ? O2 C1 1.233(3) . ? O3 C11 1.298(2) . ? O3 H21 0.812(16) . ? O4 C11 1.223(2) . ? N1 C12 1.454(2) . ? N1 H22 0.815(16) . ? C1 C2 1.491(3) . ? C2 C3 1.328(3) . ? C2 C4 1.496(3) . ? C3 C5 1.479(3) . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.391(3) . ? C5 C10 1.398(3) . ? C6 C7 1.388(3) . ? C6 H6 0.9500 . ? C7 C8 1.385(3) . ? C7 H7 0.9500 . ? C8 C9 1.395(3) . ? C9 C10 1.383(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.522(3) . ? C12 C13 1.533(3) . ? C12 H12 1.0000 . ? C13 C14 1.512(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C19 1.383(3) . ? C14 C15 1.387(3) . ? C15 C16 1.386(3) . ? C15 H15 0.9500 . ? C16 C17 1.386(4) . ? C16 H16 0.9500 . ? C17 C18 1.380(3) . ? C17 H17 0.9500 . ? C18 C19 1.381(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 S1 O6 121.15(9) . . ? O5 S1 N1 106.31(9) . . ? O6 S1 N1 106.41(9) . . ? O5 S1 C8 106.93(9) . . ? O6 S1 C8 107.80(9) . . ? N1 S1 C8 107.61(9) . . ? C1 O1 H20 111.8(17) . . ? C11 O3 H21 106.1(18) . . ? C12 N1 S1 119.66(14) . . ? C12 N1 H22 119.8(16) . . ? S1 N1 H22 116.0(16) . . ? O2 C1 O1 123.07(19) . . ? O2 C1 C2 121.9(2) . . ? O1 C1 C2 115.03(19) . . ? C3 C2 C1 117.9(2) . . ? C3 C2 C4 127.7(2) . . ? C1 C2 C4 114.36(19) . . ? C2 C3 C5 128.9(2) . . ? C2 C3 H3 115.5 . . ? C5 C3 H3 115.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 119.17(19) . . ? C6 C5 C3 118.10(19) . . ? C10 C5 C3 122.51(19) . . ? C7 C6 C5 120.8(2) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 119.3(2) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 120.77(19) . . ? C7 C8 S1 119.99(16) . . ? C9 C8 S1 119.23(15) . . ? C10 C9 C8 119.46(19) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C5 120.5(2) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? O4 C11 O3 124.61(18) . . ? O4 C11 C12 122.76(18) . . ? O3 C11 C12 112.60(17) . . ? N1 C12 C11 110.88(16) . . ? N1 C12 C13 110.97(17) . . ? C11 C12 C13 109.33(15) . . ? N1 C12 H12 108.5 . . ? C11 C12 H12 108.5 . . ? C13 C12 H12 108.5 . . ? C14 C13 C12 111.66(16) . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? C19 C14 C15 118.5(2) . . ? C19 C14 C13 120.73(19) . . ? C15 C14 C13 120.7(2) . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 119.9(2) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 119.5(2) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 120.2(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 121.0(2) . . ? C18 C19 H19 119.5 . . ? C14 C19 H19 119.5 . . ? 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 O5 S1 N1 C12 -40.01(16) . . . . ? O6 S1 N1 C12 -170.40(14) . . . . ? C8 S1 N1 C12 74.27(16) . . . . ? O2 C1 C2 C3 173.3(2) . . . . ? O1 C1 C2 C3 -8.2(3) . . . . ? O2 C1 C2 C4 -4.2(3) . . . . ? O1 C1 C2 C4 174.27(19) . . . . ? C1 C2 C3 C5 178.28(19) . . . . ? C4 C2 C3 C5 -4.6(4) . . . . ? C2 C3 C5 C6 144.0(2) . . . . ? C2 C3 C5 C10 -41.4(3) . . . . ? C10 C5 C6 C7 0.4(3) . . . . ? C3 C5 C6 C7 175.16(19) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? C6 C7 C8 C9 0.5(3) . . . . ? C6 C7 C8 S1 -178.26(16) . . . . ? O5 S1 C8 C7 15.93(19) . . . . ? O6 S1 C8 C7 147.65(16) . . . . ? N1 S1 C8 C7 -97.94(17) . . . . ? O5 S1 C8 C9 -162.84(16) . . . . ? O6 S1 C8 C9 -31.11(19) . . . . ? N1 S1 C8 C9 83.29(18) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? S1 C8 C9 C10 178.51(16) . . . . ? C8 C9 C10 C5 0.1(3) . . . . ? C6 C5 C10 C9 -0.1(3) . . . . ? C3 C5 C10 C9 -174.7(2) . . . . ? S1 N1 C12 C11 93.99(17) . . . . ? S1 N1 C12 C13 -144.30(14) . . . . ? O4 C11 C12 N1 27.1(3) . . . . ? O3 C11 C12 N1 -154.94(17) . . . . ? O4 C11 C12 C13 -95.5(2) . . . . ? O3 C11 C12 C13 82.4(2) . . . . ? N1 C12 C13 C14 64.7(2) . . . . ? C11 C12 C13 C14 -172.64(17) . . . . ? C12 C13 C14 C19 -103.2(2) . . . . ? C12 C13 C14 C15 74.5(2) . . . . ? C19 C14 C15 C16 -1.8(3) . . . . ? C13 C14 C15 C16 -179.6(2) . . . . ? C14 C15 C16 C17 1.1(4) . . . . ? C15 C16 C17 C18 1.0(4) . . . . ? C16 C17 C18 C19 -2.2(3) . . . . ? C17 C18 C19 C14 1.4(3) . . . . ? C15 C14 C19 C18 0.6(3) . . . . ? C13 C14 C19 C18 178.34(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H20 O4 0.886(17) 1.755(17) 2.6357(19) 172(2) 4_465 O3 H21 O2 0.812(16) 1.802(17) 2.603(2) 169(3) 4_766 N1 H22 O4 0.815(16) 2.156(17) 2.945(2) 163(2) 3_755 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.80 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.342 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.047 #== end