# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_wheeler _journal_name_full Chem.Commun. #TrackingRef '- wheeler-ChemComm10.CIF' _journal_coden_Cambridge 0182 #=================================================================== _audit_creation_method 'from SHELXL97 CIF, local template and enCIFer' #=================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name 'Kraig A. Wheeler' _publ_contact_author_address ; Eastern Illinios University Department of Chemistry 600 Lincoln Avenue Charleston, IL 61920 ; _publ_contact_author_email kawheeler@eiu.edu _publ_contact_author_fax 217-581-6613 _publ_contact_author_phone 217-581-3119 loop_ _publ_author_name _publ_author_address _publ_author_footnote K.A.Wheeler ; Eastern Illinios University Department of Chemistry 600 Lincoln Avenue Charleston, IL 61920-3099 ; ? R.Grove ; Eastern Illinios University Department of Chemistry 600 Lincoln Avenue Charleston, IL 61920-3099 ; ? 'Steven H. Malehorn' ; Eastern Illinios University Department of Chemistry 600 Lincoln Avenue Charleston, IL 61920-3099 ; ? 'Meghan E. Breen' ; Eastern Illinios University Department of Chemistry 600 Lincoln Avenue Charleston, IL 61920-3099 ; ? #=================================================================== data_kaw61 _database_code_depnum_ccdc_archive 'CCDC 782795' #TrackingRef '- wheeler-ChemComm10.CIF' # 1, unreacted _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N O6 S' _chemical_formula_sum 'C12 H13 N O6 S' _chemical_formula_weight 299.29 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 7.2052(2) _cell_length_b 8.2040(2) _cell_length_c 11.3088(3) _cell_angle_alpha 91.461(1) _cell_angle_beta 92.761(1) _cell_angle_gamma 90.699(1) _cell_volume 667.43(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5777 _cell_measurement_theta_min 3.539 _cell_measurement_theta_max 72.621 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 2.414 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4846 _exptl_absorpt_correction_T_max 0.7589 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _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_measurement_device_type 'Bruker APEXII CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13874 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0120 _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 -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 68.19 _reflns_number_total 2380 _reflns_number_gt 2332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2009) and XPREP (Bruker, 2009) ; _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 successive difference Fourier maps and refined with anisotropic thermal parameters. The N-H and O-H hydrogen atoms were located in difference density Fourier maps and refined independently. 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^)+(0.0408P)^2^+0.9330P] 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 2380 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 0.48926(8) 0.61981(6) 0.32522(5) 0.02456(18) Uani 1 1 d . . . O1 O 0.0829(3) -0.1380(2) -0.23463(15) 0.0343(4) Uani 1 1 d . . . N1 N 0.3041(3) 0.6588(3) 0.39746(19) 0.0278(5) Uani 1 1 d . . . C1 C 0.1583(3) -0.1538(3) -0.1285(2) 0.0263(5) Uani 1 1 d . . . O2 O 0.1819(2) -0.2875(2) -0.08159(15) 0.0297(4) Uani 1 1 d . . . C2 C 0.2116(3) 0.0019(3) -0.0685(2) 0.0275(5) Uani 1 1 d . . . H2 H 0.1902 0.1002 -0.1093 0.033 Uiso 1 1 calc R . . O3 O -0.0660(2) 0.5661(2) 0.18374(15) 0.0336(4) Uani 1 1 d . . . C3 C 0.2887(3) 0.0103(3) 0.0406(2) 0.0241(5) Uani 1 1 d . . . H3 H 0.3112 -0.0899 0.0788 0.029 Uiso 1 1 calc R . . O4 O 0.0332(2) 0.4189(2) 0.33728(15) 0.0338(4) Uani 1 1 d . . . C4 C 0.3420(3) 0.1607(3) 0.10754(19) 0.0232(5) Uani 1 1 d . . . O5 O 0.5147(3) 0.7508(2) 0.24606(15) 0.0335(4) Uani 1 1 d . . . C5 C 0.3233(3) 0.3141(3) 0.0577(2) 0.0259(5) Uani 1 1 d . . . H5 H 0.2759 0.3221 -0.0217 0.031 Uiso 1 1 calc R . . O6 O 0.6323(2) 0.5865(2) 0.41349(14) 0.0281(4) Uani 1 1 d . . . C6 C 0.3729(3) 0.4542(3) 0.1227(2) 0.0259(5) Uani 1 1 d . . . H6 H 0.3597 0.5583 0.0885 0.031 Uiso 1 1 calc R . . C7 C 0.4424(3) 0.4405(3) 0.23897(19) 0.0237(5) Uani 1 1 d . . . C8 C 0.4628(3) 0.2893(3) 0.2904(2) 0.0257(5) Uani 1 1 d . . . H8 H 0.5097 0.2816 0.3700 0.031 Uiso 1 1 calc R . . C9 C 0.4137(3) 0.1503(3) 0.2241(2) 0.0255(5) Uani 1 1 d . . . H9 H 0.4288 0.0463 0.2581 0.031 Uiso 1 1 calc R . . C10 C 0.0270(3) 0.5472(3) 0.2838(2) 0.0288(5) Uani 1 1 d . . . C11 C 0.1341(4) 0.7013(3) 0.3288(2) 0.0324(6) Uani 1 1 d . . . H11 H 0.1694 0.7653 0.2590 0.039 Uiso 1 1 calc R . . C12 C 0.0132(4) 0.8057(3) 0.4047(3) 0.0404(6) Uani 1 1 d . . . H12A H -0.0253 0.7432 0.4722 0.061 Uiso 1 1 calc R . . H12B H -0.0970 0.8387 0.3575 0.061 Uiso 1 1 calc R . . H12C H 0.0835 0.9029 0.4335 0.061 Uiso 1 1 calc R . . H13 H 0.046(6) -0.235(6) -0.271(4) 0.083(14) Uiso 1 1 d . . . H14 H -0.115(9) 0.461(8) 0.149(6) 0.15(2) Uiso 1 1 d . . . H15 H 0.287(3) 0.596(3) 0.447(2) 0.010(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0315(3) 0.0180(3) 0.0235(3) -0.0017(2) -0.0047(2) -0.0001(2) O1 0.0440(10) 0.0297(10) 0.0277(9) -0.0009(7) -0.0106(8) -0.0071(8) N1 0.0332(11) 0.0241(11) 0.0251(11) -0.0039(9) -0.0066(9) 0.0022(9) C1 0.0244(11) 0.0298(13) 0.0244(11) -0.0020(9) 0.0000(9) -0.0021(10) O2 0.0326(9) 0.0259(9) 0.0298(9) -0.0005(7) -0.0068(7) -0.0026(7) C2 0.0291(12) 0.0251(12) 0.0278(12) -0.0002(9) -0.0025(9) -0.0008(10) O3 0.0359(10) 0.0321(10) 0.0314(9) -0.0059(7) -0.0109(7) 0.0018(8) C3 0.0246(11) 0.0223(12) 0.0252(11) -0.0010(9) 0.0017(9) 0.0002(9) O4 0.0368(10) 0.0332(10) 0.0302(9) -0.0052(7) -0.0081(7) -0.0022(8) C4 0.0239(11) 0.0227(11) 0.0228(11) -0.0031(9) 0.0021(9) 0.0011(9) O5 0.0467(11) 0.0207(9) 0.0324(9) 0.0009(7) -0.0043(8) -0.0024(8) C5 0.0322(12) 0.0262(12) 0.0191(11) -0.0005(9) -0.0020(9) 0.0018(10) O6 0.0300(9) 0.0251(9) 0.0285(9) -0.0011(7) -0.0053(7) -0.0020(7) C6 0.0342(13) 0.0205(11) 0.0229(11) 0.0019(9) -0.0011(9) 0.0020(10) C7 0.0290(12) 0.0200(11) 0.0218(11) -0.0037(9) 0.0002(9) 0.0010(9) C8 0.0327(12) 0.0228(12) 0.0211(11) -0.0005(9) -0.0031(9) 0.0019(10) C9 0.0318(12) 0.0199(11) 0.0246(11) 0.0015(9) 0.0002(9) 0.0022(9) C10 0.0285(12) 0.0286(13) 0.0287(12) -0.0041(10) -0.0039(10) 0.0070(10) C11 0.0318(13) 0.0276(13) 0.0368(14) -0.0035(10) -0.0070(10) 0.0031(10) C12 0.0400(15) 0.0325(14) 0.0482(16) -0.0061(12) 0.0001(12) 0.0029(12) _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 1.4317(18) . ? S1 O6 1.4336(17) . ? S1 N1 1.628(2) . ? S1 C7 1.765(2) . ? O1 C1 1.304(3) . ? O1 H13 0.92(5) . ? N1 C11 1.469(3) . ? N1 H15 0.78(3) . ? C1 O2 1.240(3) . ? C1 C2 1.469(3) . ? C2 C3 1.329(3) . ? C2 H2 0.9500 . ? O3 C10 1.301(3) . ? O3 H14 0.99(7) . ? C3 C4 1.469(3) . ? C3 H3 0.9500 . ? O4 C10 1.228(3) . ? C4 C5 1.397(3) . ? C4 C9 1.397(3) . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 C7 1.392(3) . ? C6 H6 0.9500 . ? C7 C8 1.390(3) . ? C8 C9 1.382(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.535(4) . ? C11 C12 1.510(4) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 119.43(11) . . ? O5 S1 N1 107.35(11) . . ? O6 S1 N1 105.77(10) . . ? O5 S1 C7 107.87(10) . . ? O6 S1 C7 108.62(10) . . ? N1 S1 C7 107.21(11) . . ? C1 O1 H13 114(3) . . ? C11 N1 S1 117.90(18) . . ? C11 N1 H15 113.3(18) . . ? S1 N1 H15 112.9(17) . . ? O2 C1 O1 123.4(2) . . ? O2 C1 C2 122.8(2) . . ? O1 C1 C2 113.8(2) . . ? C3 C2 C1 122.5(2) . . ? C3 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? C10 O3 H14 112(4) . . ? C2 C3 C4 125.8(2) . . ? C2 C3 H3 117.1 . . ? C4 C3 H3 117.1 . . ? C5 C4 C9 119.1(2) . . ? C5 C4 C3 121.8(2) . . ? C9 C4 C3 119.1(2) . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 119.0(2) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C8 C7 C6 121.3(2) . . ? C8 C7 S1 119.63(17) . . ? C6 C7 S1 118.87(17) . . ? C9 C8 C7 119.0(2) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C4 120.8(2) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? O4 C10 O3 124.2(2) . . ? O4 C10 C11 122.4(2) . . ? O3 C10 C11 113.4(2) . . ? N1 C11 C12 109.6(2) . . ? N1 C11 C10 110.9(2) . . ? C12 C11 C10 110.3(2) . . ? N1 C11 H11 108.7 . . ? C12 C11 H11 108.7 . . ? C10 C11 H11 108.7 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 50.1(2) . . . . ? O6 S1 N1 C11 178.69(18) . . . . ? C7 S1 N1 C11 -65.5(2) . . . . ? O2 C1 C2 C3 -0.2(4) . . . . ? O1 C1 C2 C3 179.3(2) . . . . ? C1 C2 C3 C4 -178.6(2) . . . . ? C2 C3 C4 C5 -3.1(4) . . . . ? C2 C3 C4 C9 176.9(2) . . . . ? C9 C4 C5 C6 -0.6(3) . . . . ? C3 C4 C5 C6 179.4(2) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C5 C6 C7 S1 -175.33(18) . . . . ? O5 S1 C7 C8 162.18(19) . . . . ? O6 S1 C7 C8 31.4(2) . . . . ? N1 S1 C7 C8 -82.5(2) . . . . ? O5 S1 C7 C6 -22.3(2) . . . . ? O6 S1 C7 C6 -153.14(19) . . . . ? N1 S1 C7 C6 93.0(2) . . . . ? C6 C7 C8 C9 0.3(4) . . . . ? S1 C7 C8 C9 175.71(18) . . . . ? C7 C8 C9 C4 -0.9(4) . . . . ? C5 C4 C9 C8 1.1(3) . . . . ? C3 C4 C9 C8 -179.0(2) . . . . ? S1 N1 C11 C12 -153.53(19) . . . . ? S1 N1 C11 C10 84.5(2) . . . . ? O4 C10 C11 N1 29.3(3) . . . . ? O3 C10 C11 N1 -149.3(2) . . . . ? O4 C10 C11 C12 -92.2(3) . . . . ? O3 C10 C11 C12 89.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H13 O4 0.92(5) 1.74(5) 2.661(2) 178(4) 2 O3 H14 O2 0.99(7) 1.65(7) 2.643(2) 175(6) 2 N1 H15 O6 0.78(3) 2.27(3) 2.997(3) 156(2) 2_666 C9 H9 O5 0.95 2.51 3.379(3) 151.8 1_545 C5 H5 O3 0.95 2.52 3.399(3) 154.4 2_565 C6 H6 O2 0.95 2.62 3.426(3) 142.7 1_565 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 68.19 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.902 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.060 #== end data_kaw36 _database_code_depnum_ccdc_archive 'CCDC 782796' #TrackingRef '- wheeler-ChemComm10.CIF' # 2, unreacted _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H28 N2 O12 S2' _chemical_formula_sum 'C25 H28 N2 O12 S2' _chemical_formula_weight 612.61 _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 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' _cell_length_a 7.3133(3) _cell_length_b 8.2316(3) _cell_length_c 11.5670(4) _cell_angle_alpha 88.171(3) _cell_angle_beta 84.518(3) _cell_angle_gamma 86.427(2) _cell_volume 691.57(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2946 _cell_measurement_theta_min 3.750 _cell_measurement_theta_max 66.400 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 2.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5854 _exptl_absorpt_correction_T_max 0.9121 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _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_measurement_device_type 'Bruker APEXII CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6649 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 67.35 _reflns_number_total 3209 _reflns_number_gt 2808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2009) and XPREP (Bruker, 2009) ; _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 successive difference Fourier maps and refined with anisotropic thermal parameters. The N-H and O-H hydrogen atoms were located in difference density Fourier maps and refined independently. All other H atoms were place in calculated positions and refined with Uiso = 1.2Ueq of the corresponding C atom (Uiso = 1.5Ueq 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^)+(0.0675P)^2^+0.3149P] 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 0.25(3) _refine_ls_number_reflns 3209 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.006 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 0.31450(10) 0.34539(9) 0.63542(7) 0.0253(2) Uani 1 1 d . . . O1A O 0.8996(5) -0.1362(4) 0.5453(3) 0.0420(9) Uani 1 1 d . . . N1A N 0.4947(4) 0.3739(3) 0.7046(3) 0.0220(7) Uani 1 1 d . . . C1A C 0.9809(5) -0.1178(5) 0.4431(3) 0.0234(9) Uani 1 1 d . . . O2A O 1.0042(4) 0.0213(3) 0.3955(2) 0.0306(8) Uani 1 1 d . . . C2A C 1.0343(6) -0.2636(5) 0.3852(4) 0.0354(12) Uani 1 1 d . . . H2A H 1.0048 -0.3607 0.4238 0.043 Uiso 1 1 calc R . . O3A O 0.7827(4) -0.8123(3) 0.1405(2) 0.0291(7) Uani 1 1 d . . . C3A C 1.1268(5) -0.2737(4) 0.2761(3) 0.0207(9) Uani 1 1 d U . . H3A H 1.1566 -0.1758 0.2389 0.025 Uiso 1 1 calc R . . O4A O 0.8900(4) -0.6589(3) -0.0083(2) 0.0324(8) Uani 1 1 d . . . C4A C 1.1818(6) -0.4181(5) 0.2141(3) 0.0266(10) Uani 1 1 d . . . O5A O 1.3671(4) -1.0047(3) 0.0805(2) 0.0346(8) Uani 1 1 d . . . C5A C 1.1588(6) -0.5791(5) 0.2590(3) 0.0252(10) Uani 1 1 d . . . H5A H 1.1024 -0.5917 0.3341 0.030 Uiso 1 1 calc R . . O6A O 1.4836(4) -0.8334(3) -0.0856(2) 0.0300(7) Uani 1 1 d . . . C6A C 1.2118(5) -0.7101(5) 0.2016(3) 0.0221(9) Uani 1 1 d . . . H6A H 1.1998 -0.8129 0.2362 0.027 Uiso 1 1 calc R . . C7A C 1.2894(6) -0.6911(5) 0.0833(3) 0.0280(11) Uani 1 1 d . . . C8A C 1.3227(6) -0.5404(5) 0.0386(4) 0.0306(11) Uani 1 1 d . . . H8A H 1.3838 -0.5299 -0.0353 0.037 Uiso 1 1 calc R . . C9A C 1.2687(6) -0.4044(5) 0.0995(4) 0.0279(10) Uani 1 1 d . . . H9A H 1.2888 -0.3021 0.0660 0.034 Uiso 1 1 calc R . . C10A C 0.8764(5) -0.7975(4) 0.0475(3) 0.0265(10) Uani 1 1 d . . . C11A C 0.9912(6) -0.9447(5) -0.0008(4) 0.0415(13) Uani 1 1 d . . . H11A H 1.0190 -1.0165 0.0652 0.050 Uiso 1 1 calc R . . C12A C 0.8780(6) -1.0398(5) -0.0784(3) 0.0283(10) Uani 1 1 d . . . H12C H 0.8464 -0.9718 -0.1434 0.043 Uiso 1 1 calc R . . H12B H 0.7676 -1.0719 -0.0343 0.043 Uiso 1 1 calc R . . H12A H 0.9495 -1.1350 -0.1060 0.043 Uiso 1 1 calc R . . H14A H 0.900(5) -0.060(5) 0.580(3) 0.015(9) Uiso 1 1 d . . . H15A H 0.682(13) -0.708(10) 0.173(8) 0.17(4) Uiso 1 1 d . . . H16A H 1.152(4) -0.862(4) -0.117(3) 0.000(8) Uiso 1 1 d . . . S1B S 1.34409(11) -0.86999(9) 0.00245(7) 0.0245(2) Uani 1 1 d . . . O1B O 0.7621(4) -0.3891(3) 0.0896(3) 0.0287(8) Uani 1 1 d . . . N1B N 1.1709(5) -0.9023(5) -0.0642(3) 0.0329(10) Uani 1 1 d . . . C1B C 0.6807(6) -0.4123(5) 0.1947(3) 0.0294(11) Uani 1 1 d . . . O2B O 0.6491(4) -0.5436(4) 0.2403(3) 0.0310(8) Uani 1 1 d . . . C2B C 0.6202(6) -0.2526(4) 0.2541(4) 0.0235(10) Uani 1 1 d U . . H2B H 0.6437 -0.1541 0.2157 0.028 Uiso 1 1 calc R . . O3B O 0.8816(5) 0.2998(4) 0.4963(3) 0.0366(9) Uani 1 1 d . . . C3B C 0.5363(6) -0.2537(5) 0.3577(4) 0.0292(11) Uani 1 1 d . . . H3B H 0.5116 -0.3539 0.3931 0.035 Uiso 1 1 calc R . . O4B O 0.7707(4) 0.1403(4) 0.6479(3) 0.0323(8) Uani 1 1 d . . . C4B C 0.4758(6) -0.1021(5) 0.4245(4) 0.0223(10) Uani 1 1 d . . . O5B O 0.2861(4) 0.4822(3) 0.5566(3) 0.0297(8) Uani 1 1 d . . . C5B C 0.5084(6) 0.0471(5) 0.3739(4) 0.0274(10) Uani 1 1 d . . . H5B H 0.5643 0.0563 0.2985 0.033 Uiso 1 1 calc R . . O6B O 0.1669(4) 0.3093(3) 0.7249(3) 0.0290(8) Uani 1 1 d . . . C6B C 0.4531(6) 0.1903(5) 0.4413(4) 0.0280(11) Uani 1 1 d . . . H6B H 0.4765 0.2936 0.4107 0.034 Uiso 1 1 calc R . . C7B C 0.3676(6) 0.1721(4) 0.5485(4) 0.0203(9) Uani 1 1 d . . . C8B C 0.3382(6) 0.0196(5) 0.6030(3) 0.0224(10) Uani 1 1 d . . . H8B H 0.2860 0.0099 0.6793 0.027 Uiso 1 1 calc R . . C9B C 0.3927(6) -0.1184(5) 0.5353(4) 0.0244(10) Uani 1 1 d . . . H9B H 0.3717 -0.2219 0.5664 0.029 Uiso 1 1 calc R . . C10B C 0.7756(6) 0.2653(5) 0.5963(4) 0.0303(11) Uani 1 1 d U . . C11B C 0.6588(6) 0.4203(5) 0.6369(3) 0.0230(10) Uani 1 1 d . . . H11B H 0.6263 0.4868 0.5692 0.028 Uiso 1 1 calc R . . C12B C 0.7641(8) 0.5159(6) 0.7111(6) 0.0582(17) Uani 1 1 d . . . H12E H 0.8738 0.5496 0.6651 0.070 Uiso 1 1 calc R . . H12D H 0.8038 0.4451 0.7738 0.070 Uiso 1 1 calc R . . C13B C 0.6600(6) 0.6682(5) 0.7645(4) 0.0423(10) Uani 1 1 d . . . H13A H 0.5452 0.6384 0.8043 0.063 Uiso 1 1 calc R . . H13B H 0.6368 0.7471 0.7040 0.063 Uiso 1 1 calc R . . H13C H 0.7331 0.7139 0.8185 0.063 Uiso 1 1 calc R . . H14B H 0.819(7) -0.506(6) 0.060(4) 0.050(14) Uiso 1 1 d . . . H15B H 0.908(5) 0.205(5) 0.471(3) 0.021(9) Uiso 1 1 d . . . H16B H 0.515(5) 0.292(4) 0.753(3) 0.008(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1A 0.0283(5) 0.0214(4) 0.0259(5) -0.0010(3) -0.0005(4) -0.0018(4) O1A 0.049(2) 0.0346(16) 0.0382(17) -0.0083(14) 0.0117(15) 0.0088(14) N1A 0.0234(16) 0.0168(14) 0.0282(16) -0.0108(12) -0.0071(12) -0.0075(12) C1A 0.0032(16) 0.032(2) 0.033(2) 0.0065(16) 0.0026(13) -0.0020(14) O2A 0.0274(16) 0.0298(14) 0.0331(16) 0.0027(12) 0.0029(12) -0.0003(12) C2A 0.031(2) 0.041(2) 0.034(2) 0.0218(18) 0.0056(17) -0.0151(18) O3A 0.0336(16) 0.0275(14) 0.0253(14) 0.0028(11) 0.0040(12) -0.0075(12) C3A 0.0053(15) 0.0304(18) 0.0273(18) 0.0149(15) -0.0101(12) -0.0037(13) O4A 0.0445(17) 0.0226(13) 0.0287(14) -0.0054(11) 0.0093(12) -0.0092(12) C4A 0.024(2) 0.030(2) 0.0257(19) 0.0137(16) -0.0088(15) -0.0002(16) O5A 0.0492(19) 0.0215(14) 0.0307(16) -0.0014(12) 0.0088(14) -0.0023(13) C5A 0.027(2) 0.030(2) 0.0181(17) 0.0067(15) 0.0021(14) -0.0062(15) O6A 0.0236(15) 0.0345(15) 0.0302(15) -0.0040(12) 0.0047(11) 0.0024(11) C6A 0.0248(19) 0.0258(19) 0.0161(17) 0.0043(14) -0.0016(14) -0.0086(15) C7A 0.026(2) 0.044(2) 0.0135(17) 0.0014(16) 0.0045(15) -0.0051(17) C8A 0.025(2) 0.038(2) 0.027(2) 0.0003(17) 0.0058(16) -0.0016(17) C9A 0.028(2) 0.0213(18) 0.034(2) 0.0089(16) 0.0006(17) -0.0072(16) C10A 0.032(2) 0.0197(18) 0.0305(19) 0.0019(15) -0.0208(16) 0.0026(15) C11A 0.020(2) 0.036(2) 0.065(3) -0.014(2) 0.0224(19) -0.0078(17) C12A 0.031(2) 0.034(2) 0.0208(17) 0.0009(15) -0.0087(15) 0.0004(16) S1B 0.0254(5) 0.0192(4) 0.0271(5) -0.0005(4) 0.0065(4) 0.0007(4) O1B 0.0334(18) 0.0285(16) 0.0222(15) 0.0009(12) 0.0069(12) -0.0009(13) N1B 0.037(2) 0.035(2) 0.0211(18) 0.0121(15) 0.0153(15) 0.0079(16) C1B 0.042(3) 0.027(2) 0.0196(19) -0.0147(17) -0.0053(17) 0.0079(19) O2B 0.0320(18) 0.0272(16) 0.0323(17) -0.0048(13) 0.0052(13) 0.0003(13) C2B 0.025(2) 0.0147(17) 0.0309(19) -0.0190(15) -0.0053(15) 0.0104(15) O3B 0.0334(18) 0.0346(16) 0.0391(18) -0.0112(13) 0.0171(14) -0.0064(13) C3B 0.042(3) 0.0176(18) 0.028(2) -0.0168(16) 0.0025(17) 0.0026(17) O4B 0.0253(17) 0.0395(17) 0.0297(16) -0.0015(14) 0.0028(13) 0.0096(13) C4B 0.016(2) 0.0222(19) 0.029(2) -0.0157(16) 0.0001(15) 0.0005(15) O5B 0.0288(17) 0.0231(15) 0.0374(18) 0.0028(13) -0.0070(13) 0.0020(12) C5B 0.028(2) 0.030(2) 0.024(2) -0.0097(17) -0.0004(16) 0.0011(17) O6B 0.0305(18) 0.0221(14) 0.0329(16) 0.0016(12) 0.0040(13) -0.0011(12) C6B 0.034(2) 0.0183(19) 0.031(2) 0.0007(17) -0.0018(18) 0.0010(17) C7B 0.023(2) 0.0029(15) 0.036(2) -0.0035(14) -0.0082(16) 0.0020(14) C8B 0.036(2) 0.0128(17) 0.0184(19) 0.0015(15) 0.0016(16) -0.0038(16) C9B 0.027(2) 0.022(2) 0.024(2) -0.0018(16) -0.0012(17) 0.0025(16) C10B 0.022(2) 0.038(2) 0.028(2) -0.0074(18) 0.0227(16) -0.0135(17) C11B 0.033(2) 0.025(2) 0.0129(17) 0.0047(15) -0.0123(15) -0.0039(17) C12B 0.033(3) 0.037(3) 0.106(5) -0.029(3) 0.003(3) -0.016(2) C13B 0.042(2) 0.035(2) 0.051(2) -0.0081(17) -0.0021(18) -0.0103(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1A O5B 1.443(3) . ? S1A O6B 1.460(3) . ? S1A N1A 1.639(3) . ? S1A C7B 1.773(4) . ? O1A C1A 1.280(5) . ? O1A H14A 0.76(4) . ? N1A C11B 1.435(5) . ? N1A H16B 0.88(3) . ? C1A O2A 1.269(5) . ? C1A C2A 1.408(6) . ? C2A C3A 1.376(5) . ? C2A H2A 0.9300 . ? O3A C10A 1.226(5) . ? O3A H15A 1.15(9) . ? C3A C4A 1.424(6) . ? C3A H3A 0.9300 . ? O4A C10A 1.297(5) . ? C4A C9A 1.418(6) . ? C4A C5A 1.422(5) . ? O5A S1B 1.420(3) . ? C5A C6A 1.303(5) . ? C5A H5A 0.9300 . ? O6A S1B 1.411(3) . ? C6A C7A 1.438(5) . ? C6A H6A 0.9300 . ? C7A C8A 1.356(6) . ? C7A S1B 1.774(4) . ? C8A C9A 1.359(6) . ? C8A H8A 0.9300 . ? C9A H9A 0.9300 . ? C10A C11A 1.521(6) . ? C11A N1B 1.498(5) . ? C11A C12A 1.540(6) . ? C11A H11A 0.9800 . ? C12A H12C 0.9600 . ? C12A H12B 0.9600 . ? C12A H12A 0.9600 . ? S1B N1B 1.584(4) . ? O1B C1B 1.315(5) . ? O1B H14B 1.08(5) . ? N1B H16A 0.71(3) . ? C1B O2B 1.214(5) . ? C1B C2B 1.523(5) . ? C2B C3B 1.293(6) . ? C2B H2B 0.9300 . ? O3B C10B 1.362(5) . ? O3B H15B 0.84(4) . ? C3B C4B 1.509(5) . ? C3B H3B 0.9300 . ? O4B C10B 1.174(5) . ? C4B C5B 1.368(6) . ? C4B C9B 1.371(6) . ? C5B C6B 1.449(6) . ? C5B H5B 0.9300 . ? C6B C7B 1.343(6) . ? C6B H6B 0.9300 . ? C7B C8B 1.406(5) . ? C8B C9B 1.415(5) . ? C8B H8B 0.9300 . ? C9B H9B 0.9300 . ? C10B C11B 1.551(6) . ? C11B C12B 1.481(7) . ? C11B H11B 0.9800 . ? C12B C13B 1.541(6) . ? C12B H12E 0.9700 . ? C12B H12D 0.9700 . ? C13B H13A 0.9600 . ? C13B H13B 0.9600 . ? C13B H13C 0.9600 . ? 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 O5B S1A O6B 118.52(18) . . ? O5B S1A N1A 108.69(17) . . ? O6B S1A N1A 105.93(18) . . ? O5B S1A C7B 106.64(18) . . ? O6B S1A C7B 108.99(18) . . ? N1A S1A C7B 107.65(17) . . ? C1A O1A H14A 111(3) . . ? C11B N1A S1A 117.6(2) . . ? C11B N1A H16B 113(2) . . ? S1A N1A H16B 111(2) . . ? O2A C1A O1A 122.5(4) . . ? O2A C1A C2A 122.4(3) . . ? O1A C1A C2A 115.0(3) . . ? C3A C2A C1A 125.2(4) . . ? C3A C2A H2A 117.4 . . ? C1A C2A H2A 117.4 . . ? C10A O3A H15A 120(4) . . ? C2A C3A C4A 127.0(4) . . ? C2A C3A H3A 116.5 . . ? C4A C3A H3A 116.5 . . ? C9A C4A C5A 116.1(4) . . ? C9A C4A C3A 119.1(3) . . ? C5A C4A C3A 124.8(4) . . ? C6A C5A C4A 124.1(4) . . ? C6A C5A H5A 118.0 . . ? C4A C5A H5A 118.0 . . ? C5A C6A C7A 118.1(3) . . ? C5A C6A H6A 120.9 . . ? C7A C6A H6A 120.9 . . ? C8A C7A C6A 119.8(4) . . ? C8A C7A S1B 122.5(3) . . ? C6A C7A S1B 117.7(3) . . ? C7A C8A C9A 121.4(4) . . ? C7A C8A H8A 119.3 . . ? C9A C8A H8A 119.3 . . ? C8A C9A C4A 120.2(4) . . ? C8A C9A H9A 119.9 . . ? C4A C9A H9A 119.9 . . ? O3A C10A O4A 122.6(4) . . ? O3A C10A C11A 118.9(4) . . ? O4A C10A C11A 118.4(4) . . ? N1B C11A C10A 113.3(4) . . ? N1B C11A C12A 111.1(4) . . ? C10A C11A C12A 109.9(4) . . ? N1B C11A H11A 107.4 . . ? C10A C11A H11A 107.4 . . ? C12A C11A H11A 107.4 . . ? C11A C12A H12C 109.5 . . ? C11A C12A H12B 109.5 . . ? H12C C12A H12B 109.5 . . ? C11A C12A H12A 109.5 . . ? H12C C12A H12A 109.5 . . ? H12B C12A H12A 109.5 . . ? O6A S1B O5A 121.08(18) . . ? O6A S1B N1B 104.98(18) . . ? O5A S1B N1B 106.31(19) . . ? O6A S1B C7A 107.21(18) . . ? O5A S1B C7A 109.06(18) . . ? N1B S1B C7A 107.5(2) . . ? C1B O1B H14B 107(3) . . ? C11A N1B S1B 121.9(3) . . ? C11A N1B H16A 108(3) . . ? S1B N1B H16A 123(3) . . ? O2B C1B O1B 125.5(4) . . ? O2B C1B C2B 122.2(4) . . ? O1B C1B C2B 112.3(4) . . ? C3B C2B C1B 120.3(4) . . ? C3B C2B H2B 119.9 . . ? C1B C2B H2B 119.9 . . ? C10B O3B H15B 101(3) . . ? C2B C3B C4B 124.0(4) . . ? C2B C3B H3B 118.0 . . ? C4B C3B H3B 118.0 . . ? C5B C4B C9B 121.9(4) . . ? C5B C4B C3B 119.2(4) . . ? C9B C4B C3B 118.8(4) . . ? C4B C5B C6B 118.0(4) . . ? C4B C5B H5B 121.0 . . ? C6B C5B H5B 121.0 . . ? C7B C6B C5B 119.2(4) . . ? C7B C6B H6B 120.4 . . ? C5B C6B H6B 120.4 . . ? C6B C7B C8B 123.4(4) . . ? C6B C7B S1A 119.4(3) . . ? C8B C7B S1A 116.6(3) . . ? C7B C8B C9B 116.2(4) . . ? C7B C8B H8B 121.9 . . ? C9B C8B H8B 121.9 . . ? C4B C9B C8B 121.1(4) . . ? C4B C9B H9B 119.4 . . ? C8B C9B H9B 119.4 . . ? O4B C10B O3B 127.3(4) . . ? O4B C10B C11B 123.0(3) . . ? O3B C10B C11B 109.7(4) . . ? N1A C11B C12B 108.1(4) . . ? N1A C11B C10B 109.4(3) . . ? C12B C11B C10B 109.8(4) . . ? N1A C11B H11B 109.8 . . ? C12B C11B H11B 109.8 . . ? C10B C11B H11B 109.8 . . ? C11B C12B C13B 115.6(4) . . ? C11B C12B H12E 108.4 . . ? C13B C12B H12E 108.4 . . ? C11B C12B H12D 108.4 . . ? C13B C12B H12D 108.4 . . ? H12E C12B H12D 107.4 . . ? C12B C13B H13A 109.5 . . ? C12B C13B H13B 109.5 . . ? H13A C13B H13B 109.5 . . ? C12B C13B H13C 109.5 . . ? H13A C13B H13C 109.5 . . ? H13B C13B H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5B S1A N1A C11B -48.4(3) . . . . ? O6B S1A N1A C11B -176.8(3) . . . . ? C7B S1A N1A C11B 66.7(3) . . . . ? O2A C1A C2A C3A 4.5(7) . . . . ? O1A C1A C2A C3A -178.5(4) . . . . ? C1A C2A C3A C4A -179.4(4) . . . . ? C2A C3A C4A C9A 177.0(4) . . . . ? C2A C3A C4A C5A -4.0(7) . . . . ? C9A C4A C5A C6A -0.1(6) . . . . ? C3A C4A C5A C6A -179.2(4) . . . . ? C4A C5A C6A C7A -3.5(7) . . . . ? C5A C6A C7A C8A 6.7(6) . . . . ? C5A C6A C7A S1B -175.1(3) . . . . ? C6A C7A C8A C9A -6.2(7) . . . . ? S1B C7A C8A C9A 175.6(4) . . . . ? C7A C8A C9A C4A 2.5(7) . . . . ? C5A C4A C9A C8A 0.8(6) . . . . ? C3A C4A C9A C8A 179.9(4) . . . . ? O3A C10A C11A N1B -144.9(4) . . . . ? O4A C10A C11A N1B 31.2(6) . . . . ? O3A C10A C11A C12A 90.1(5) . . . . ? O4A C10A C11A C12A -93.8(4) . . . . ? C8A C7A S1B O6A 23.2(4) . . . . ? C6A C7A S1B O6A -155.0(3) . . . . ? C8A C7A S1B O5A 155.9(4) . . . . ? C6A C7A S1B O5A -22.3(4) . . . . ? C8A C7A S1B N1B -89.2(4) . . . . ? C6A C7A S1B N1B 92.6(4) . . . . ? C10A C11A N1B S1B 80.3(5) . . . . ? C12A C11A N1B S1B -155.3(3) . . . . ? O6A S1B N1B C11A -179.7(3) . . . . ? O5A S1B N1B C11A 50.9(4) . . . . ? C7A S1B N1B C11A -65.7(4) . . . . ? O2B C1B C2B C3B 1.8(7) . . . . ? O1B C1B C2B C3B 179.4(4) . . . . ? C1B C2B C3B C4B 178.3(4) . . . . ? C2B C3B C4B C5B 0.8(7) . . . . ? C2B C3B C4B C9B -178.1(4) . . . . ? C9B C4B C5B C6B 0.4(7) . . . . ? C3B C4B C5B C6B -178.5(4) . . . . ? C4B C5B C6B C7B -2.0(7) . . . . ? C5B C6B C7B C8B 4.2(7) . . . . ? C5B C6B C7B S1A 175.5(3) . . . . ? O5B S1A C7B C6B 29.7(4) . . . . ? O6B S1A C7B C6B 158.7(4) . . . . ? N1A S1A C7B C6B -86.8(4) . . . . ? O5B S1A C7B C8B -158.5(3) . . . . ? O6B S1A C7B C8B -29.4(4) . . . . ? N1A S1A C7B C8B 85.1(3) . . . . ? C6B C7B C8B C9B -4.4(7) . . . . ? S1A C7B C8B C9B -175.9(3) . . . . ? C5B C4B C9B C8B -0.7(7) . . . . ? C3B C4B C9B C8B 178.1(4) . . . . ? C7B C8B C9B C4B 2.5(6) . . . . ? S1A N1A C11B C12B 152.1(3) . . . . ? S1A N1A C11B C10B -88.3(3) . . . . ? O4B C10B C11B N1A -27.4(6) . . . . ? O3B C10B C11B N1A 153.6(3) . . . . ? O4B C10B C11B C12B 91.1(6) . . . . ? O3B C10B C11B C12B -87.9(5) . . . . ? N1A C11B C12B C13B -56.8(6) . . . . ? C10B C11B C12B C13B -176.2(4) . . . . ? 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 N1A H16B O6A 0.88(3) 2.10(3) 2.919(4) 155(3) 1_466 N1B H16A O6B 0.71(3) 2.27(3) 2.954(4) 162(3) 1_544 O1B H14B O4A 1.08(5) 1.54(5) 2.606(4) 168(4) . O3A H15A O2B 1.15(9) 1.58(9) 2.618(4) 148(8) . O3B H15B O2A 0.84(4) 1.84(4) 2.671(4) 168(4) . O1A H14A O4B 0.76(4) 1.99(4) 2.678(4) 151(4) . C9B H9B O5B 0.93 2.56 3.422(5) 154.0 1_545 C9A H9A O5A 0.93 2.56 3.407(5) 151.2 1_565 C5B H5B O3A 0.93 2.57 3.422(5) 152.9 1_565 C6B H6B O2B 0.93 2.61 3.418(5) 145.0 1_565 C5A H5A O3B 0.93 2.53 3.413(5) 157.7 1_545 C6A H6A O2A 0.93 2.62 3.416(5) 143.6 1_545 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 67.35 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.436 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.062 #== end data_kaw87b _database_code_depnum_ccdc_archive 'CCDC 782797' #TrackingRef '- wheeler-ChemComm10.CIF' # 1: 72% converted to photoproduct _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H13 N O6 S' _chemical_formula_sum 'C12 H13 N O6 S' _chemical_formula_weight 299.29 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 7.1475(1) _cell_length_b 8.1722(1) _cell_length_c 11.5458(2) _cell_angle_alpha 91.920(1) _cell_angle_beta 93.863(1) _cell_angle_gamma 94.634(1) _cell_volume 670.153(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5837 _cell_measurement_theta_min 3.481 _cell_measurement_theta_max 72.107 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 2.414 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.456 _exptl_absorpt_correction_T_max 0.851 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _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 ? _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13739 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 68.24 _reflns_number_total 2379 _reflns_number_gt 1978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2009) and XPREP (Bruker, 2009) ; _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 successive difference Fourier maps and refined with anisotropic thermal parameters. The ratio of observed reactant and photoproduct phases were determined by refining occupancy factors. It was determined that the ratio of reactant to photoproduct was 28:72. The reactant phase phenyl ring (C4-C9) was refined using rigid body model so as to approximate the geometry of the photoproduct phenyl ring (C4a-C9a) using the SAME command in SHELXL The N-H and O-H hydrogen atoms were located in difference density Fourier maps and refined independently. The carboxyl H atoms were constrained to 0.85(2) angstroms. All other H atoms were place in calculated positions and refined with Uiso = 1.2Ueq of the corresponding C atom (Uiso = 1.5Ueq 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^)+(0.0684P)^2^+0.2596P] 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 2379 _refine_ls_number_parameters 267 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1296 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.046 _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 0.51101(9) 0.87762(8) 0.17457(6) 0.0575(2) Uani 1 1 d . . . O1 O 0.8843(4) 1.6368(3) 0.74926(18) 0.0832(6) Uani 1 1 d D A . O2 O 0.8080(3) 1.7736(3) 0.59123(18) 0.0768(6) Uani 1 1 d . A . O3 O 1.0780(3) 0.9338(3) 0.30595(18) 0.0739(6) Uani 1 1 d D . . O4 O 0.9960(3) 1.0730(2) 0.15150(17) 0.0726(5) Uani 1 1 d . . . O5 O 0.4790(3) 0.7461(2) 0.24977(18) 0.0747(6) Uani 1 1 d . A . O6 O 0.3683(3) 0.9125(2) 0.08893(17) 0.0700(5) Uani 1 1 d . A . N1 N 0.6899(3) 0.8396(3) 0.1016(2) 0.0589(5) Uani 1 1 d . A . C1 C 0.8485(5) 1.6474(4) 0.6397(2) 0.0710(8) Uani 1 1 d . . . H14 H 1.134(9) 1.028(4) 0.330(6) 0.22(3) Uiso 1 1 d D . . H13 H 0.892(7) 1.733(3) 0.785(4) 0.155(19) Uiso 1 1 d D . . H15 H 0.713(4) 0.909(3) 0.051(3) 0.055(8) Uiso 1 1 d . . . C2 C 0.7568(18) 1.4962(12) 0.5695(9) 0.070(3) Uani 0.290(5) 1 d P A 1 H2 H 0.7456 1.3994 0.6095 0.084 Uiso 0.290(5) 1 calc PR A 1 C3 C 0.6916(13) 1.4855(11) 0.4600(7) 0.055(2) Uani 0.290(5) 1 d P A 1 H3 H 0.6750 1.5833 0.4232 0.066 Uiso 0.290(5) 1 calc PR A 1 C4 C 0.6422(16) 1.3293(10) 0.3896(8) 0.048(2) Uani 0.290(5) 1 d PD A 1 C5 C 0.586(2) 1.332(2) 0.2743(12) 0.053(4) Uani 0.290(5) 1 d PD A 1 H5 H 0.5661 1.4329 0.2422 0.063 Uiso 0.290(5) 1 calc PR A 1 C6 C 0.557(7) 1.191(3) 0.203(2) 0.067(8) Uani 0.290(5) 1 d PD A 1 H6 H 0.5444 1.1981 0.1228 0.081 Uiso 0.290(5) 1 calc PR A 1 C7 C 0.547(4) 1.038(3) 0.2529(19) 0.038(4) Uani 0.290(5) 1 d PD A 1 C8 C 0.604(4) 1.032(2) 0.368(2) 0.061(6) Uani 0.290(5) 1 d PD A 1 H8 H 0.6114 0.9309 0.4014 0.073 Uiso 0.290(5) 1 calc PR A 1 C9 C 0.6504(18) 1.1737(15) 0.4365(11) 0.058(3) Uani 0.290(5) 1 d PD A 1 H9 H 0.6878 1.1655 0.5147 0.070 Uiso 0.290(5) 1 calc PR A 1 C10 C 0.9870(4) 0.9479(3) 0.2079(2) 0.0597(6) Uani 1 1 d . A . C11 C 0.8619(4) 0.7956(3) 0.1643(2) 0.0624(7) Uani 1 1 d . . . H11 H 0.8260 0.7342 0.2320 0.075 Uiso 1 1 calc R A . C12 C 0.9667(5) 0.6858(4) 0.0892(3) 0.0811(9) Uani 1 1 d . A . H12A H 0.8848 0.5916 0.0617 0.122 Uiso 1 1 calc R . . H12B H 1.0734 0.6506 0.1337 0.122 Uiso 1 1 calc R . . H12C H 1.0088 0.7452 0.0241 0.122 Uiso 1 1 calc R . . C2A C 0.9162(6) 1.4976(4) 0.5765(3) 0.0575(10) Uani 0.710(5) 1 d P . 2 H2A H 0.8756 1.3947 0.6122 0.069 Uiso 0.710(5) 1 calc PR A 2 C3A C 0.8661(6) 1.4902(4) 0.4438(3) 0.0565(11) Uani 0.710(5) 1 d P . 2 H3A H 0.8111 1.5911 0.4202 0.068 Uiso 0.710(5) 1 calc PR A 2 C4A C 0.7501(8) 1.3411(5) 0.3883(3) 0.0516(10) Uani 0.710(5) 1 d PD A 2 C5A C 0.6606(9) 1.3537(9) 0.2791(5) 0.0576(16) Uani 0.710(5) 1 d PD A 2 H5A H 0.6587 1.4563 0.2467 0.069 Uiso 0.710(5) 1 calc PR A 2 C6A C 0.574(3) 1.2168(11) 0.2169(8) 0.057(2) Uani 0.710(5) 1 d PD A 2 H6A H 0.5075 1.2267 0.1456 0.068 Uiso 0.710(5) 1 calc PR A 2 C7A C 0.5890(16) 1.0647(11) 0.2649(9) 0.047(2) Uani 0.710(5) 1 d PD A 2 C8A C 0.6630(14) 1.0491(9) 0.3760(7) 0.055(2) Uani 0.710(5) 1 d PD A 2 H8A H 0.6585 0.9473 0.4098 0.066 Uiso 0.710(5) 1 calc PR A 2 C9A C 0.7450(8) 1.1888(6) 0.4373(4) 0.0590(13) Uani 0.710(5) 1 d PD A 2 H9A H 0.7973 1.1798 0.5125 0.071 Uiso 0.710(5) 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 0.0600(4) 0.0510(4) 0.0604(4) 0.0017(3) -0.0035(3) 0.0040(2) O1 0.1129(18) 0.0718(15) 0.0610(12) -0.0120(10) 0.0001(11) -0.0050(12) O2 0.0915(15) 0.0664(14) 0.0700(12) -0.0130(10) -0.0091(10) 0.0102(10) O3 0.0896(14) 0.0640(13) 0.0651(12) -0.0053(9) -0.0211(10) 0.0142(10) O4 0.0884(14) 0.0591(12) 0.0665(12) -0.0013(9) -0.0181(10) 0.0037(9) O5 0.0869(14) 0.0590(12) 0.0772(13) 0.0088(9) 0.0018(10) 0.0007(9) O6 0.0604(11) 0.0731(13) 0.0738(12) 0.0048(9) -0.0111(9) 0.0008(8) N1 0.0667(13) 0.0522(13) 0.0560(13) -0.0031(10) -0.0086(10) 0.0069(10) C1 0.095(2) 0.0607(19) 0.0547(15) -0.0100(13) 0.0125(14) -0.0084(14) C2 0.094(9) 0.046(6) 0.066(6) 0.000(4) -0.002(5) -0.003(5) C3 0.064(6) 0.051(5) 0.048(4) 0.001(3) -0.002(4) -0.002(4) C4 0.046(5) 0.036(4) 0.060(5) -0.009(3) 0.001(5) 0.003(4) C5 0.064(9) 0.040(7) 0.051(6) 0.002(5) -0.010(6) -0.002(6) C6 0.101(17) 0.048(11) 0.053(9) -0.016(7) 0.008(9) 0.007(8) C7 0.033(9) 0.038(8) 0.040(7) 0.006(5) -0.010(4) -0.006(5) C8 0.071(15) 0.042(7) 0.068(10) -0.001(5) -0.009(8) 0.006(6) C9 0.066(7) 0.065(7) 0.042(5) 0.002(4) -0.010(6) 0.001(6) C10 0.0608(15) 0.0552(16) 0.0625(15) -0.0067(12) -0.0084(12) 0.0160(11) C11 0.0680(16) 0.0518(15) 0.0664(16) -0.0018(11) -0.0064(13) 0.0102(11) C12 0.079(2) 0.0592(18) 0.105(2) -0.0154(16) 0.0059(17) 0.0134(14) C2A 0.077(3) 0.049(2) 0.0434(17) -0.0044(14) -0.0046(16) 0.0001(16) C3A 0.080(3) 0.043(2) 0.0443(18) -0.0027(13) -0.0085(16) 0.0078(15) C4A 0.064(3) 0.045(2) 0.0444(18) -0.0039(13) -0.0073(19) 0.0098(19) C5A 0.078(5) 0.043(3) 0.050(2) 0.0037(17) -0.011(3) 0.003(3) C6A 0.080(4) 0.046(4) 0.043(3) 0.004(3) -0.015(3) 0.012(4) C7A 0.049(6) 0.039(3) 0.051(3) -0.009(2) -0.005(3) 0.000(3) C8A 0.075(6) 0.045(3) 0.044(3) 0.005(2) -0.007(3) 0.005(3) C9A 0.084(4) 0.051(2) 0.040(2) 0.0004(15) -0.015(3) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O5 1.418(2) . ? S1 O6 1.4246(19) . ? S1 C7 1.56(2) . ? S1 N1 1.623(2) . ? S1 C7A 1.848(8) . ? O1 C1 1.281(4) . ? O1 H13 0.87(2) . ? O2 C1 1.235(4) . ? O3 C10 1.280(3) . ? O3 H14 0.87(2) . ? O4 C10 1.230(3) . ? N1 C11 1.461(3) . ? N1 H15 0.84(3) . ? C1 C2 1.531(10) . ? C1 C2A 1.533(5) . ? C2 C3 1.315(13) . ? C2 H2 0.9300 . ? C3 C4 1.494(12) . ? C3 H3 0.9300 . ? C4 C5 1.366(14) . ? C4 C9 1.403(12) . ? C5 C6 1.390(16) . ? C5 H5 0.9300 . ? C6 C7 1.390(15) . ? C6 H6 0.9300 . ? C7 C8 1.369(15) . ? C8 C9 1.381(15) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.523(4) . ? C11 C12 1.504(4) . ? C11 H11 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C2A C3A 1.548(5) . ? C2A C3A 1.585(6) 2_786 ? C2A H2A 0.9800 . ? C3A C4A 1.515(5) . ? C3A C2A 1.585(6) 2_786 ? C3A H3A 0.9800 . ? C4A C9A 1.383(6) . ? C4A C5A 1.385(6) . ? C5A C6A 1.388(9) . ? C5A H5A 0.9300 . ? C6A C7A 1.387(7) . ? C6A H6A 0.9300 . ? C7A C8A 1.369(8) . ? C8A C9A 1.389(7) . ? C8A H8A 0.9300 . ? C9A H9A 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 O5 S1 O6 120.14(12) . . ? O5 S1 C7 106.9(8) . . ? O6 S1 C7 104.7(9) . . ? O5 S1 N1 107.56(13) . . ? O6 S1 N1 104.78(12) . . ? C7 S1 N1 113.0(11) . . ? O5 S1 C7A 108.1(3) . . ? O6 S1 C7A 110.0(3) . . ? C7 S1 C7A 8.1(14) . . ? N1 S1 C7A 105.3(4) . . ? C1 O1 H13 112(3) . . ? C10 O3 H14 110(5) . . ? C11 N1 S1 118.9(2) . . ? C11 N1 H15 111.5(19) . . ? S1 N1 H15 113.7(19) . . ? O2 C1 O1 124.9(3) . . ? O2 C1 C2 109.8(5) . . ? O1 C1 C2 118.8(5) . . ? O2 C1 C2A 124.0(3) . . ? O1 C1 C2A 109.1(3) . . ? C2 C1 C2A 43.5(5) . . ? C3 C2 C1 128.4(8) . . ? C3 C2 H2 115.8 . . ? C1 C2 H2 115.8 . . ? C2 C3 C4 125.5(9) . . ? C2 C3 H3 117.3 . . ? C4 C3 H3 117.3 . . ? C5 C4 C9 116.5(10) . . ? C5 C4 C3 120.7(10) . . ? C9 C4 C3 122.8(9) . . ? C4 C5 C6 122.5(15) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C5 C6 C7 119.6(19) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 117.5(16) . . ? C8 C7 S1 121.1(15) . . ? C6 C7 S1 120.3(15) . . ? C7 C8 C9 121.8(16) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C9 C4 120.9(13) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? O4 C10 O3 124.2(2) . . ? O4 C10 C11 121.1(2) . . ? O3 C10 C11 114.7(2) . . ? N1 C11 C12 110.6(2) . . ? N1 C11 C10 111.3(2) . . ? C12 C11 C10 110.9(2) . . ? N1 C11 H11 108.0 . . ? C12 C11 H11 108.0 . . ? C10 C11 H11 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 C2A C3A 113.7(3) . . ? C1 C2A C3A 115.0(3) . 2_786 ? C3A C2A C3A 90.8(3) . 2_786 ? C1 C2A H2A 111.9 . . ? C3A C2A H2A 111.9 . . ? C3A C2A H2A 111.9 2_786 . ? C4A C3A C2A 119.3(3) . . ? C4A C3A C2A 116.0(3) . 2_786 ? C2A C3A C2A 89.2(3) . 2_786 ? C4A C3A H3A 110.2 . . ? C2A C3A H3A 110.2 . . ? C2A C3A H3A 110.2 2_786 . ? C9A C4A C5A 118.5(4) . . ? C9A C4A C3A 122.4(4) . . ? C5A C4A C3A 118.7(4) . . ? C4A C5A C6A 121.6(6) . . ? C4A C5A H5A 119.2 . . ? C6A C5A H5A 119.2 . . ? C7A C6A C5A 117.5(7) . . ? C7A C6A H6A 121.2 . . ? C5A C6A H6A 121.2 . . ? C8A C7A C6A 122.1(7) . . ? C8A C7A S1 119.2(6) . . ? C6A C7A S1 118.7(7) . . ? C7A C8A C9A 118.5(6) . . ? C7A C8A H8A 120.7 . . ? C9A C8A H8A 120.7 . . ? C4A C9A C8A 121.1(5) . . ? C4A C9A H9A 119.4 . . ? C8A C9A H9A 119.4 . . ? 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 O5 S1 N1 C11 -50.0(2) . . . . ? O6 S1 N1 C11 -178.88(19) . . . . ? C7 S1 N1 C11 67.7(9) . . . . ? C7A S1 N1 C11 65.1(4) . . . . ? O2 C1 C2 C3 19.3(14) . . . . ? O1 C1 C2 C3 172.4(10) . . . . ? C2A C1 C2 C3 -99.6(13) . . . . ? C1 C2 C3 C4 165.9(9) . . . . ? C2 C3 C4 C5 -176.2(12) . . . . ? C2 C3 C4 C9 3.8(17) . . . . ? C9 C4 C5 C6 -7(3) . . . . ? C3 C4 C5 C6 173(3) . . . . ? C4 C5 C6 C7 13(6) . . . . ? C5 C6 C7 C8 -13(6) . . . . ? C5 C6 C7 S1 179(3) . . . . ? O5 S1 C7 C8 21(3) . . . . ? O6 S1 C7 C8 150(2) . . . . ? N1 S1 C7 C8 -97(2) . . . . ? C7A S1 C7 C8 -78(8) . . . . ? O5 S1 C7 C6 -171(3) . . . . ? O6 S1 C7 C6 -43(3) . . . . ? N1 S1 C7 C6 71(3) . . . . ? C7A S1 C7 C6 89(8) . . . . ? C6 C7 C8 C9 7(5) . . . . ? S1 C7 C8 C9 175(2) . . . . ? C7 C8 C9 C4 0(3) . . . . ? C5 C4 C9 C8 0(2) . . . . ? C3 C4 C9 C8 -179.9(16) . . . . ? S1 N1 C11 C12 150.9(2) . . . . ? S1 N1 C11 C10 -85.4(3) . . . . ? O4 C10 C11 N1 -34.6(4) . . . . ? O3 C10 C11 N1 145.1(2) . . . . ? O4 C10 C11 C12 89.0(3) . . . . ? O3 C10 C11 C12 -91.3(3) . . . . ? O2 C1 C2A C3A -19.9(5) . . . . ? O1 C1 C2A C3A 175.4(3) . . . . ? C2 C1 C2A C3A 63.4(6) . . . . ? O2 C1 C2A C3A 82.9(4) . . . 2_786 ? O1 C1 C2A C3A -81.7(3) . . . 2_786 ? C2 C1 C2A C3A 166.2(7) . . . 2_786 ? C1 C2A C3A C4A -122.4(4) . . . . ? C3A C2A C3A C4A 119.7(4) 2_786 . . . ? C1 C2A C3A C2A 117.9(4) . . . 2_786 ? C3A C2A C3A C2A 0.0 2_786 . . 2_786 ? C2A C3A C4A C9A -24.8(7) . . . . ? C2A C3A C4A C9A 80.0(5) 2_786 . . . ? C2A C3A C4A C5A 161.6(5) . . . . ? C2A C3A C4A C5A -93.6(5) 2_786 . . . ? C9A C4A C5A C6A -2.6(13) . . . . ? C3A C4A C5A C6A 171.2(11) . . . . ? C4A C5A C6A C7A -4(2) . . . . ? C5A C6A C7A C8A 9(2) . . . . ? C5A C6A C7A S1 -169.7(10) . . . . ? O5 S1 C7A C8A 20.9(10) . . . . ? O6 S1 C7A C8A 153.8(8) . . . . ? C7 S1 C7A C8A 104(8) . . . . ? N1 S1 C7A C8A -93.8(9) . . . . ? O5 S1 C7A C6A -160.3(11) . . . . ? O6 S1 C7A C6A -27.4(13) . . . . ? C7 S1 C7A C6A -77(8) . . . . ? N1 S1 C7A C6A 85.0(12) . . . . ? C6A C7A C8A C9A -7.7(18) . . . . ? S1 C7A C8A C9A 171.1(7) . . . . ? C5A C4A C9A C8A 4.2(9) . . . . ? C3A C4A C9A C8A -169.4(6) . . . . ? C7A C8A C9A C4A 0.8(13) . . . . ? 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 H13 O4 0.87(2) 1.82(3) 2.651(3) 157(5) 2_786 O3 H14 O2 0.87(2) 1.83(3) 2.675(3) 163(7) 2_786 N1 H15 O6 0.84(3) 2.29(3) 3.070(3) 154(2) 2_675 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.363 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.045 #== end data_kaw89b _database_code_depnum_ccdc_archive 'CCDC 782798' #TrackingRef '- wheeler-ChemComm10.CIF' # 2, 62% converted to photoproduct _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H28 N2 O12 S2' _chemical_formula_sum 'C25 H28 N2 O12 S2' _chemical_formula_weight 612.61 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.2486(2) _cell_length_b 8.1094(2) _cell_length_c 11.8857(3) _cell_angle_alpha 89.015(2) _cell_angle_beta 82.881(2) _cell_angle_gamma 83.670(2) _cell_volume 689.05(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2117 _cell_measurement_theta_min 2.501 _cell_measurement_theta_max 23.453 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_correction_T_min 0.554 _exptl_absorpt_process_details 'SADABS (Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4, APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7005 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0343 _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 -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4837 _reflns_number_gt 3436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2009) and XPREP (Bruker, 2009) ; _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 successive difference Fourier maps and refined with anisotropic thermal parameters. The ratio of observed reactant and photoproduct phases were determined by refining occupancy factors. It was determined that the ratio of ractant to photoproduct was 39:61. The reactant phase phenyl rings (C4a-C9a and C4b-C9b) were refined using rigid body model so as to approximate the geometry of the photoproduct phenyl ring (C4c-C9c and C4d-C9d, respectively) using the SAME command in SHELXL The N-H and O-H hydrogen atoms were located in difference density Fourier maps and refined independently and constrained to 0.85(2)angstroms. All other H atoms were place in calculated positions and refined with Ueq = 1.2Uiso of the corresponding C atom (Ueq = 1.5Uiso 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^)+(0.0446P)^2^+0.2179P] 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 0.10(14) _refine_ls_number_reflns 4837 _refine_ls_number_parameters 463 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.144 _refine_ls_shift/su_max 0.164 _refine_ls_shift/su_mean 0.035 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 0.88397(11) 0.75242(10) 0.08983(8) 0.0587(3) Uani 1 1 d . . . O1A O 0.4486(5) 1.4935(4) 0.6545(3) 0.1014(13) Uani 1 1 d D A . O2A O 0.5447(4) 1.6308(4) 0.4963(3) 0.0822(11) Uani 1 1 d . A . O3A O 0.3093(4) 0.8117(4) 0.2170(2) 0.0733(10) Uani 1 1 d D . . O4A O 0.4082(5) 0.9625(4) 0.0696(3) 0.0847(11) Uani 1 1 d . . . O5A O 0.9174(4) 0.6170(3) 0.1594(2) 0.0669(9) Uani 1 1 d . A . O6A O 1.0285(4) 0.7950(4) 0.0032(3) 0.0766(11) Uani 1 1 d . A . N1A N 0.7120(5) 0.7224(4) 0.0221(3) 0.0638(11) Uani 1 1 d D A . C1A C 0.5044(7) 1.4952(5) 0.5458(4) 0.0772(15) Uani 1 1 d . . . C2A C 0.6151(9) 1.3435(7) 0.4740(5) 0.068(4) Uani 0.3730(16) 1 d P A 1 H2A H 0.6273 1.2449 0.5149 0.081 Uiso 0.3730(16) 1 calc PR A 1 C3A C 0.6885(9) 1.3316(7) 0.3737(5) 0.067(4) Uani 0.3730(16) 1 d PR A 1 H3A H 0.7304 1.4290 0.3430 0.080 Uiso 0.3730(16) 1 d PR A 1 C4A C 0.7191(9) 1.1961(7) 0.2986(5) 0.046(2) Uiso 0.3730(16) 1 d PRD A 1 C5A C 0.7174(10) 1.0424(9) 0.3441(6) 0.056(3) Uiso 0.3730(16) 1 d PD A 1 H5A H 0.6961 1.0299 0.4224 0.067 Uiso 0.3730(16) 1 calc PR A 1 C6A C 0.7466(10) 0.9043(9) 0.2761(6) 0.044(3) Uiso 0.3730(16) 1 d PRD A 1 H6A H 0.7328 0.8009 0.3091 0.052 Uiso 0.3730(16) 1 calc PR A 1 C7A C 0.7955(12) 0.9137(9) 0.1613(7) 0.032(2) Uiso 0.3730(16) 1 d PD A 1 C8A C 0.8633(13) 1.0704(10) 0.1237(8) 0.038(2) Uiso 0.3730(16) 1 d PD A 1 H8A H 0.9376 1.0758 0.0543 0.045 Uiso 0.3730(16) 1 calc PR A 1 C9A C 0.8210(13) 1.2044(11) 0.1865(8) 0.051(3) Uiso 0.3730(16) 1 d PD A 1 H9A H 0.8569 1.3054 0.1585 0.061 Uiso 0.3730(16) 1 calc PR A 1 C10A C 0.4099(6) 0.8267(5) 0.1267(4) 0.0578(12) Uani 1 1 d . A . C11A C 0.5352(5) 0.6763(5) 0.0809(4) 0.0625(13) Uani 1 1 d . . . H11A H 0.5650 0.6067 0.1458 0.075 Uiso 1 1 calc R A . C12A C 0.4471(6) 0.5731(5) 0.0043(4) 0.0739(15) Uani 1 1 d . A . H12A H 0.4219 0.6360 -0.0623 0.111 Uiso 1 1 calc R . . H12B H 0.3321 0.5413 0.0431 0.111 Uiso 1 1 calc R . . H12C H 0.5306 0.4754 -0.0173 0.111 Uiso 1 1 calc R . . H16B H 0.040(3) 1.951(2) 0.8582(10) 0.018(6) Uiso 1 1 d D . . H15A H 0.261(4) 0.9051(17) 0.246(2) 0.074(11) Uiso 1 1 d D . . H16A H 0.679(5) 0.811(2) -0.014(2) 0.082(14) Uiso 1 1 d D . . S1B S -0.14930(12) 1.97771(10) 0.72938(9) 0.0595(3) Uani 1 1 d . . . O1B O 0.2770(5) 1.2453(3) 0.1706(3) 0.0810(11) Uani 1 1 d D A . O2B O 0.1804(5) 1.0968(4) 0.3194(3) 0.0841(12) Uani 1 1 d . A . O3B O 0.4272(5) 1.9249(4) 0.5961(3) 0.0835(12) Uani 1 1 d D . . O4B O 0.3280(4) 1.7717(3) 0.7451(3) 0.0706(10) Uani 1 1 d . . . O5B O -0.1762(5) 2.1217(4) 0.6564(3) 0.0823(12) Uani 1 1 d . A . O6B O -0.2929(4) 1.9378(4) 0.8124(3) 0.0725(11) Uani 1 1 d . A . N1B N 0.0223(5) 2.0046(4) 0.7976(3) 0.0526(10) Uani 1 1 d D A . C1B C 0.2273(8) 1.2209(6) 0.2731(5) 0.0773(16) Uani 1 1 d . . . C2B C 0.1359(14) 1.3671(15) 0.3461(9) 0.067(4) Uani 0.3730(16) 1 d P A 1 H2B H 0.1377 1.4698 0.3102 0.080 Uiso 0.3730(16) 1 calc PR A 1 C3B C 0.0559(12) 1.3726(12) 0.4501(8) 0.047(3) Uani 0.3730(16) 1 d P A 1 H3B H 0.0419 1.2723 0.4876 0.056 Uiso 0.3730(16) 1 calc PR A 1 C4B C -0.0191(13) 1.5371(10) 0.5172(7) 0.045(2) Uiso 0.3730(16) 1 d PD A 1 C5B C 0.0067(16) 1.7037(12) 0.4703(9) 0.067(4) Uiso 0.3730(16) 1 d PD A 1 H5B H 0.0565 1.7180 0.3953 0.080 Uiso 0.3730(16) 1 calc PR A 1 C6B C -0.0455(16) 1.8372(13) 0.5415(8) 0.058(3) Uiso 0.3730(16) 1 d PD A 1 H6B H -0.0401 1.9439 0.5123 0.069 Uiso 0.3730(16) 1 calc PR A 1 C7B C -0.1059(12) 1.8167(9) 0.6557(7) 0.0213(19) Uiso 0.3730(16) 1 d PD A 1 C8B C -0.125(3) 1.6639(14) 0.6966(13) 0.089(6) Uiso 0.3730(16) 1 d PD A 1 H8B H -0.1761 1.6498 0.7714 0.107 Uiso 0.3730(16) 1 calc PR A 1 C9B C -0.0682(17) 1.5249(14) 0.6269(9) 0.057(4) Uiso 0.3730(16) 1 d PD A 1 H9B H -0.0652 1.4199 0.6598 0.068 Uiso 0.3730(16) 1 calc PR A 1 C10B C 0.3252(6) 1.8977(6) 0.6954(4) 0.0688(15) Uani 1 1 d . A . C11B C 0.1950(6) 2.0514(5) 0.7373(4) 0.0614(14) Uani 1 1 d . . . H11B H 0.1670 2.1218 0.6724 0.074 Uiso 1 1 calc R A . C12B C 0.2989(8) 2.1440(7) 0.8141(6) 0.106(2) Uani 1 1 d . A . H12E H 0.4097 2.1805 0.7709 0.128 Uiso 1 1 calc R . . H12D H 0.3386 2.0706 0.8739 0.128 Uiso 1 1 calc R . . C13B C 0.1682(6) 2.3013(5) 0.8688(4) 0.0898(14) Uani 1 1 d . . . H13C H 0.1658 2.3906 0.8148 0.135 Uiso 1 1 calc R A . H13A H 0.2166 2.3356 0.9352 0.135 Uiso 1 1 calc R . . H13B H 0.0436 2.2721 0.8893 0.135 Uiso 1 1 calc R . . C2C C 0.4422(9) 1.3593(8) 0.4879(5) 0.0562(19) Uani 0.6270(16) 1 d P A 2 H2C H 0.4780 1.2527 0.5237 0.067 Uiso 0.6270(16) 1 calc PR A 2 C3C C 0.5049(8) 1.3529(8) 0.3539(5) 0.0488(17) Uani 0.6270(16) 1 d P A 2 H3C H 0.5633 1.4531 0.3296 0.059 Uiso 0.6270(16) 1 calc PR A 2 C4C C 0.6242(10) 1.2052(8) 0.3063(5) 0.065(2) Uani 0.6270(16) 1 d PD A 2 C5C C 0.6242(11) 1.0518(8) 0.3429(5) 0.067(2) Uani 0.6270(16) 1 d PD A 2 H5C H 0.5470 1.0350 0.4097 0.081 Uiso 0.6270(16) 1 calc PR A 2 C6C C 0.7277(14) 0.9107(9) 0.2924(6) 0.086(3) Uani 0.6270(16) 1 d PD A 2 H6C H 0.7331 0.8090 0.3300 0.104 Uiso 0.6270(16) 1 calc PR A 2 C7C C 0.8203(10) 0.9268(8) 0.1866(5) 0.051(2) Uani 0.6270(16) 1 d PD A 2 C8C C 0.8120(10) 1.0914(8) 0.1366(6) 0.057(2) Uani 0.6270(16) 1 d PD A 2 H8C H 0.8557 1.1049 0.0604 0.068 Uiso 0.6270(16) 1 calc PR A 2 C9C C 0.7416(9) 1.2242(7) 0.1998(6) 0.059(2) Uani 0.6270(16) 1 d PD A 2 H9C H 0.7681 1.3295 0.1751 0.070 Uiso 0.6270(16) 1 calc PR A 2 C2D C 0.2937(12) 1.3779(9) 0.3371(6) 0.067(2) Uani 0.6270(16) 1 d P A 2 H2D H 0.2569 1.4851 0.3025 0.080 Uiso 0.6270(16) 1 calc PR A 2 C3D C 0.2283(12) 1.3713(8) 0.4588(6) 0.070(3) Uani 0.6270(16) 1 d P A 2 H3D H 0.1741 1.2675 0.4784 0.084 Uiso 0.6270(16) 1 calc PR A 2 C4D C 0.1056(9) 1.5200(6) 0.5184(5) 0.0498(19) Uani 0.6270(16) 1 d PD A 2 C5D C 0.1128(9) 1.6825(5) 0.4680(5) 0.0489(19) Uani 0.6270(16) 1 d PD A 2 H5D H 0.1685 1.6960 0.3942 0.059 Uiso 0.6270(16) 1 calc PR A 2 H14B H 0.3353 1.1291 0.1402 0.28(4) Uiso 1 1 d RD . . H14A H 0.3847 1.6147 0.6879 0.88(19) Uiso 1 1 d RD . . H15B H 0.5011 1.8240 0.5793 1.4(4) Uiso 1 1 d RD . . C6D C 0.0345(9) 1.8167(8) 0.5328(5) 0.0474(18) Uani 0.6270(16) 1 d PD A 2 H6D H 0.0495 1.9244 0.5082 0.057 Uiso 0.6270(16) 1 calc PR A 2 C7D C -0.0670(11) 1.7869(8) 0.6355(6) 0.052(2) Uani 0.6270(16) 1 d PD A 2 C8D C -0.0884(14) 1.6405(7) 0.6828(7) 0.060(3) Uani 0.6270(16) 1 d PD A 2 H8D H -0.1617 1.6272 0.7516 0.072 Uiso 0.6270(16) 1 calc PR A 2 C9D C 0.0107(12) 1.5056(8) 0.6188(6) 0.061(2) Uani 0.6270(16) 1 d PD A 2 H9D H 0.0082 1.3999 0.6502 0.073 Uiso 0.6270(16) 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 0.0521(5) 0.0577(6) 0.0658(7) 0.0057(5) -0.0049(5) -0.0066(5) O1A 0.108(3) 0.114(3) 0.082(2) 0.005(2) -0.022(2) -0.001(2) O2A 0.090(2) 0.0618(18) 0.092(2) -0.0184(17) -0.0012(19) -0.0029(17) O3A 0.0775(18) 0.0771(19) 0.0622(18) -0.0083(16) 0.0191(16) -0.0253(16) O4A 0.091(2) 0.079(2) 0.079(2) -0.0135(17) 0.0012(18) 0.0055(18) O5A 0.0722(17) 0.0574(16) 0.0726(19) 0.0084(15) -0.0195(15) -0.0031(14) O6A 0.0557(17) 0.094(2) 0.076(2) 0.0058(18) 0.0040(16) -0.0048(16) N1A 0.069(2) 0.064(2) 0.056(2) -0.0125(18) 0.0049(18) -0.0138(18) C1A 0.117(4) 0.051(2) 0.067(3) -0.005(2) -0.036(3) 0.007(2) C2A 0.094(8) 0.039(5) 0.069(8) 0.004(5) -0.013(7) 0.001(5) C3A 0.098(8) 0.043(5) 0.060(6) -0.024(5) -0.019(6) 0.003(5) C10A 0.065(2) 0.044(2) 0.069(3) 0.0070(19) -0.020(2) -0.0176(19) C11A 0.044(2) 0.058(2) 0.084(3) -0.004(2) 0.001(2) -0.0141(19) C12A 0.059(2) 0.052(2) 0.115(4) -0.022(2) -0.013(2) -0.0225(18) S1B 0.0575(6) 0.0535(6) 0.0659(7) 0.0050(5) -0.0002(6) -0.0085(5) O1B 0.111(3) 0.0610(18) 0.064(2) -0.0265(16) 0.0044(19) 0.0061(18) O2B 0.093(2) 0.095(3) 0.065(2) -0.0157(19) -0.0054(19) -0.017(2) O3B 0.090(2) 0.065(2) 0.088(3) 0.0000(18) 0.023(2) -0.0117(18) O4B 0.077(2) 0.0524(17) 0.074(2) 0.0131(16) 0.0230(17) -0.0115(15) O5B 0.091(2) 0.0521(18) 0.100(3) 0.0219(18) -0.002(2) -0.0050(17) O6B 0.0547(18) 0.0672(19) 0.089(2) 0.0153(18) 0.0153(17) -0.0067(15) N1B 0.0524(19) 0.0484(19) 0.056(2) 0.0074(17) -0.0038(17) -0.0058(16) C1B 0.100(4) 0.060(3) 0.073(3) -0.020(3) -0.037(3) 0.016(3) C2B 0.047(6) 0.078(8) 0.069(8) 0.006(7) -0.008(6) 0.020(6) C3B 0.047(5) 0.048(5) 0.044(6) 0.023(4) -0.007(5) 0.000(4) C10B 0.046(2) 0.083(3) 0.073(3) -0.024(3) 0.026(2) -0.019(2) C11B 0.067(3) 0.057(3) 0.061(3) -0.003(2) -0.008(2) -0.012(2) C12B 0.094(4) 0.097(4) 0.131(5) -0.020(4) -0.040(4) 0.008(3) C13B 0.103(3) 0.071(3) 0.103(3) -0.027(2) -0.032(3) -0.018(2) C2C 0.059(4) 0.062(4) 0.045(3) -0.008(3) 0.005(3) -0.009(3) C3C 0.051(3) 0.064(3) 0.036(3) -0.001(3) -0.007(3) -0.025(3) C4C 0.068(4) 0.076(4) 0.048(4) -0.008(3) 0.028(3) -0.034(3) C5C 0.078(5) 0.077(5) 0.039(4) -0.008(3) 0.015(4) -0.001(4) C6C 0.169(9) 0.055(4) 0.036(4) 0.005(3) 0.006(5) -0.036(5) C7C 0.072(4) 0.049(4) 0.042(4) 0.002(3) -0.027(3) -0.030(3) C8C 0.050(4) 0.073(5) 0.043(4) 0.011(3) 0.013(3) -0.009(3) C9C 0.046(4) 0.041(3) 0.083(5) -0.013(3) 0.020(4) -0.013(3) C2D 0.103(6) 0.046(4) 0.051(4) -0.003(3) -0.024(4) 0.010(4) C3D 0.105(6) 0.034(3) 0.062(5) -0.004(3) 0.009(5) 0.008(4) C4D 0.061(4) 0.030(3) 0.059(4) -0.005(3) -0.018(4) 0.007(3) C5D 0.071(5) 0.038(3) 0.040(4) 0.007(3) -0.012(3) -0.011(3) C6D 0.040(3) 0.047(4) 0.052(4) 0.009(3) 0.003(3) -0.001(3) C7D 0.058(4) 0.051(4) 0.042(4) -0.018(3) 0.012(3) -0.001(3) C8D 0.086(6) 0.026(3) 0.062(5) 0.005(3) 0.016(4) -0.007(4) C9D 0.082(6) 0.038(4) 0.056(5) 0.013(3) 0.011(4) -0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1A O5A 1.381(3) . ? S1A O6A 1.441(3) . ? S1A C7A 1.600(8) . ? S1A N1A 1.607(4) . ? S1A C7C 1.821(6) . ? O1A C1A 1.306(6) . ? O1A H14A 1.0981 . ? O2A C1A 1.283(5) . ? O3A C10A 1.233(5) . ? O3A H15A 0.859(10) . ? O4A C10A 1.283(5) . ? N1A C11A 1.464(5) . ? N1A H16A 0.855(10) . ? C1A C2C 1.451(8) . ? C1A C2A 1.592(7) . ? C2A C3A 1.2457 . ? C2A H2A 0.9300 . ? C3A C4A 1.4082 . ? C3A H3A 0.9300 . ? C4A C5A 1.351(8) . ? C4A C9A 1.445(10) . ? C5A C6A 1.3748 . ? C5A H5A 0.9300 . ? C6A C7A 1.369(9) . ? C6A H6A 0.9300 . ? C7A C8A 1.456(10) . ? C8A C9A 1.315(11) . ? C8A H8A 0.9300 . ? C9A H9A 0.9300 . ? C10A C11A 1.505(5) . ? C11A C12A 1.492(6) . ? C11A H11A 0.9800 . ? C12A H12A 0.9600 . ? C12A H12B 0.9600 . ? C12A H12C 0.9600 . ? S1B O6B 1.404(3) . ? S1B O5B 1.452(3) . ? S1B C7B 1.565(8) . ? S1B N1B 1.603(4) . ? S1B C7D 1.920(7) . ? O1B C1B 1.245(6) . ? O1B H14B 1.0410 . ? O2B C1B 1.201(6) . ? O3B C10B 1.342(5) . ? O3B H15B 0.9373 . ? O4B C10B 1.171(5) . ? O4B H14A 1.4482 . ? N1B C11B 1.448(5) . ? N1B H16B 0.850(9) . ? C1B C2B 1.523(12) . ? C1B C2D 1.641(9) . ? C2B C3B 1.297(13) . ? C2B H2B 0.9300 . ? C3B C4B 1.575(12) . ? C3B H3B 0.9300 . ? C4B C9B 1.314(12) . ? C4B C5B 1.474(11) . ? C5B C6B 1.377(12) . ? C5B H5B 0.9300 . ? C6B C7B 1.386(11) . ? C6B H6B 0.9300 . ? C7B C8B 1.339(13) . ? C8B C9B 1.404(14) . ? C8B H8B 0.9300 . ? C9B H9B 0.9300 . ? C10B C11B 1.529(6) . ? C11B C12B 1.511(8) . ? C11B H11B 0.9800 . ? C12B C13B 1.599(7) . ? C12B H12E 0.9700 . ? C12B H12D 0.9700 . ? C13B H13C 0.9600 . ? C13B H13A 0.9600 . ? C13B H13B 0.9600 . ? C2C C3C 1.601(8) . ? C2C C3D 1.622(11) . ? C2C H2C 0.9800 . ? C3C C4C 1.476(9) . ? C3C C2D 1.559(10) . ? C3C H3C 0.9800 . ? C4C C5C 1.310(8) . ? C4C C9C 1.452(8) . ? C5C C6C 1.398(9) . ? C5C H5C 0.9300 . ? C6C C7C 1.362(9) . ? C6C H6C 0.9300 . ? C7C C8C 1.450(8) . ? C8C C9C 1.340(8) . ? C8C H8C 0.9300 . ? C9C H9C 0.9300 . ? C2D C3D 1.467(10) . ? C2D H2D 0.9800 . ? C3D C4D 1.543(9) . ? C3D H3D 0.9800 . ? C4D C9D 1.312(9) . ? C4D C5D 1.442(7) . ? C5D C6D 1.372(7) . ? C5D H5D 0.9300 . ? C6D C7D 1.376(8) . ? C6D H6D 0.9300 . ? C7D C8D 1.321(8) . ? C8D C9D 1.418(9) . ? C8D H8D 0.9300 . ? C9D H9D 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 O5A S1A O6A 119.93(18) . . ? O5A S1A C7A 111.6(3) . . ? O6A S1A C7A 110.1(3) . . ? O5A S1A N1A 108.25(18) . . ? O6A S1A N1A 104.56(18) . . ? C7A S1A N1A 100.2(3) . . ? O5A S1A C7C 104.6(2) . . ? O6A S1A C7C 108.8(2) . . ? C7A S1A C7C 10.8(4) . . ? N1A S1A C7C 110.7(3) . . ? C1A O1A H14A 113.4 . . ? C10A O3A H15A 113.1(19) . . ? C11A N1A S1A 121.6(3) . . ? C11A N1A H16A 104(2) . . ? S1A N1A H16A 109(2) . . ? O2A C1A O1A 120.2(4) . . ? O2A C1A C2C 123.4(5) . . ? O1A C1A C2C 111.8(5) . . ? O2A C1A C2A 108.6(4) . . ? O1A C1A C2A 125.6(4) . . ? C2C C1A C2A 47.7(4) . . ? C3A C2A C1A 132.3(3) . . ? C3A C2A H2A 113.8 . . ? C1A C2A H2A 113.8 . . ? C2A C3A C4A 131.2 . . ? C2A C3A H3A 114.4 . . ? C4A C3A H3A 114.4 . . ? C5A C4A C3A 117.5(4) . . ? C5A C4A C9A 115.3(6) . . ? C3A C4A C9A 122.6(4) . . ? C4A C5A C6A 120.8(4) . . ? C4A C5A H5A 119.6 . . ? C6A C5A H5A 119.6 . . ? C7A C6A C5A 122.3(4) . . ? C7A C6A H6A 118.9 . . ? C5A C6A H6A 118.8 . . ? C6A C7A C8A 113.7(7) . . ? C6A C7A S1A 120.9(6) . . ? C8A C7A S1A 116.6(6) . . ? C9A C8A C7A 120.9(8) . . ? C9A C8A H8A 119.6 . . ? C7A C8A H8A 119.6 . . ? C8A C9A C4A 120.6(8) . . ? C8A C9A H9A 119.7 . . ? C4A C9A H9A 119.7 . . ? O3A C10A O4A 122.9(4) . . ? O3A C10A C11A 117.8(4) . . ? O4A C10A C11A 119.3(4) . . ? N1A C11A C12A 109.4(4) . . ? N1A C11A C10A 111.3(3) . . ? C12A C11A C10A 113.8(3) . . ? N1A C11A H11A 107.4 . . ? C12A C11A H11A 107.3 . . ? C10A C11A H11A 107.4 . . ? C11A C12A H12A 109.5 . . ? C11A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C11A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? O6B S1B O5B 120.80(19) . . ? O6B S1B C7B 103.1(3) . . ? O5B S1B C7B 109.7(3) . . ? O6B S1B N1B 105.2(2) . . ? O5B S1B N1B 106.9(2) . . ? C7B S1B N1B 111.0(3) . . ? O6B S1B C7D 108.8(3) . . ? O5B S1B C7D 108.4(3) . . ? C7B S1B C7D 6.6(4) . . ? N1B S1B C7D 105.8(3) . . ? C1B O1B H14B 104.2 . . ? C10B O3B H15B 104.5 . . ? C10B O4B H14A 121.5 . . ? C11B N1B S1B 119.9(3) . . ? C11B N1B H16B 112.1(16) . . ? S1B N1B H16B 121.6(16) . . ? O2B C1B O1B 129.0(5) . . ? O2B C1B C2B 107.3(6) . . ? O1B C1B C2B 118.8(6) . . ? O2B C1B C2D 124.9(5) . . ? O1B C1B C2D 104.3(5) . . ? C2B C1B C2D 42.4(5) . . ? C3B C2B C1B 130.9(10) . . ? C3B C2B H2B 114.5 . . ? C1B C2B H2B 114.5 . . ? C2B C3B C4B 124.6(9) . . ? C2B C3B H3B 117.7 . . ? C4B C3B H3B 117.7 . . ? C9B C4B C5B 117.6(9) . . ? C9B C4B C3B 117.7(8) . . ? C5B C4B C3B 123.0(7) . . ? C6B C5B C4B 117.6(9) . . ? C6B C5B H5B 121.2 . . ? C4B C5B H5B 121.2 . . ? C7B C6B C5B 121.7(9) . . ? C7B C6B H6B 119.1 . . ? C5B C6B H6B 119.2 . . ? C8B C7B C6B 119.3(9) . . ? C8B C7B S1B 123.8(8) . . ? C6B C7B S1B 116.8(6) . . ? C7B C8B C9B 120.2(12) . . ? C7B C8B H8B 119.9 . . ? C9B C8B H8B 119.9 . . ? C4B C9B C8B 122.7(11) . . ? C4B C9B H9B 118.6 . . ? C8B C9B H9B 118.7 . . ? O4B C10B O3B 125.7(4) . . ? O4B C10B C11B 122.2(4) . . ? O3B C10B C11B 112.1(4) . . ? N1B C11B C12B 110.9(4) . . ? N1B C11B C10B 110.7(3) . . ? C12B C11B C10B 106.9(4) . . ? N1B C11B H11B 109.4 . . ? C12B C11B H11B 109.4 . . ? C10B C11B H11B 109.4 . . ? C11B C12B C13B 110.5(4) . . ? C11B C12B H12E 109.5 . . ? C13B C12B H12E 109.5 . . ? C11B C12B H12D 109.5 . . ? C13B C12B H12D 109.6 . . ? H12E C12B H12D 108.1 . . ? C12B C13B H13C 109.5 . . ? C12B C13B H13A 109.5 . . ? H13C C13B H13A 109.5 . . ? C12B C13B H13B 109.5 . . ? H13C C13B H13B 109.5 . . ? H13A C13B H13B 109.5 . . ? C1A C2C C3C 114.8(5) . . ? C1A C2C C3D 119.8(5) . . ? C3C C2C C3D 86.9(5) . . ? C1A C2C H2C 111.0 . . ? C3C C2C H2C 111.0 . . ? C3D C2C H2C 111.1 . . ? C4C C3C C2D 119.8(6) . . ? C4C C3C C2C 118.3(5) . . ? C2D C3C C2C 88.1(5) . . ? C4C C3C H3C 109.6 . . ? C2D C3C H3C 109.6 . . ? C2C C3C H3C 109.6 . . ? C5C C4C C9C 114.4(6) . . ? C5C C4C C3C 127.5(6) . . ? C9C C4C C3C 117.8(5) . . ? C4C C5C C6C 127.1(6) . . ? C4C C5C H5C 116.5 . . ? C6C C5C H5C 116.5 . . ? C7C C6C C5C 117.9(6) . . ? C7C C6C H6C 121.1 . . ? C5C C6C H6C 121.0 . . ? C6C C7C C8C 117.4(6) . . ? C6C C7C S1A 122.5(5) . . ? C8C C7C S1A 116.9(5) . . ? C9C C8C C7C 120.2(6) . . ? C9C C8C H8C 119.9 . . ? C7C C8C H8C 119.9 . . ? C8C C9C C4C 120.5(6) . . ? C8C C9C H9C 119.7 . . ? C4C C9C H9C 119.7 . . ? C3D C2D C3C 94.2(6) . . ? C3D C2D C1B 109.6(6) . . ? C3C C2D C1B 112.8(5) . . ? C3D C2D H2D 112.9 . . ? C3C C2D H2D 112.9 . . ? C1B C2D H2D 112.9 . . ? C2D C3D C4D 120.6(6) . . ? C2D C3D C2C 90.5(6) . . ? C4D C3D C2C 111.8(6) . . ? C2D C3D H3D 110.8 . . ? C4D C3D H3D 110.7 . . ? C2C C3D H3D 110.7 . . ? C9D C4D C5D 119.0(5) . . ? C9D C4D C3D 121.8(6) . . ? C5D C4D C3D 118.8(6) . . ? C6D C5D C4D 117.7(5) . . ? C6D C5D H5D 121.1 . . ? C4D C5D H5D 121.1 . . ? C7D C6D C5D 117.9(6) . . ? C7D C6D H6D 121.0 . . ? C5D C6D H6D 121.1 . . ? C8D C7D C6D 126.7(7) . . ? C8D C7D S1B 116.6(5) . . ? C6D C7D S1B 115.8(5) . . ? C7D C8D C9D 113.7(7) . . ? C7D C8D H8D 123.1 . . ? C9D C8D H8D 123.1 . . ? C4D C9D C8D 124.4(6) . . ? C4D C9D H9D 117.8 . . ? C8D C9D H9D 117.8 . . ? 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 O5A S1A N1A C11A 51.2(3) . . . . ? O6A S1A N1A C11A -179.9(3) . . . . ? C7A S1A N1A C11A -65.8(4) . . . . ? C7C S1A N1A C11A -62.9(4) . . . . ? O2A C1A C2A C3A -20.0(6) . . . . ? O1A C1A C2A C3A -173.5(3) . . . . ? C2C C1A C2A C3A 98.5(5) . . . . ? C1A C2A C3A C4A -151.1(4) . . . . ? C2A C3A C4A C5A -20.1(5) . . . . ? C2A C3A C4A C9A -175.1(6) . . . . ? C3A C4A C5A C6A -179.8 . . . . ? C9A C4A C5A C6A -23.0(8) . . . . ? C4A C5A C6A C7A 6.1(5) . . . . ? C5A C6A C7A C8A 16.2(9) . . . . ? C5A C6A C7A S1A 162.5(4) . . . . ? O5A S1A C7A C6A -5.6(8) . . . . ? O6A S1A C7A C6A -141.5(6) . . . . ? N1A S1A C7A C6A 108.8(7) . . . . ? C7C S1A C7A C6A -56.9(18) . . . . ? O5A S1A C7A C8A 139.8(6) . . . . ? O6A S1A C7A C8A 3.9(8) . . . . ? N1A S1A C7A C8A -105.8(7) . . . . ? C7C S1A C7A C8A 89(2) . . . . ? C6A C7A C8A C9A -21.6(13) . . . . ? S1A C7A C8A C9A -169.5(8) . . . . ? C7A C8A C9A C4A 5.2(14) . . . . ? C5A C4A C9A C8A 17.3(12) . . . . ? C3A C4A C9A C8A 172.8(7) . . . . ? S1A N1A C11A C12A -150.0(3) . . . . ? S1A N1A C11A C10A 83.4(4) . . . . ? O3A C10A C11A N1A -145.7(4) . . . . ? O4A C10A C11A N1A 36.1(6) . . . . ? O3A C10A C11A C12A 90.1(5) . . . . ? O4A C10A C11A C12A -88.0(5) . . . . ? O6B S1B N1B C11B -178.7(3) . . . . ? O5B S1B N1B C11B -49.2(3) . . . . ? C7B S1B N1B C11B 70.5(4) . . . . ? C7D S1B N1B C11B 66.2(4) . . . . ? O2B C1B C2B C3B 14.7(13) . . . . ? O1B C1B C2B C3B 172.2(9) . . . . ? C2D C1B C2B C3B -108.4(14) . . . . ? C1B C2B C3B C4B 175.0(9) . . . . ? C2B C3B C4B C9B -168.9(11) . . . . ? C2B C3B C4B C5B -4.6(15) . . . . ? C9B C4B C5B C6B -8.2(16) . . . . ? C3B C4B C5B C6B -172.6(9) . . . . ? C4B C5B C6B C7B 5.2(16) . . . . ? C5B C6B C7B C8B -4.1(18) . . . . ? C5B C6B C7B S1B 176.3(9) . . . . ? O6B S1B C7B C8B -30.9(12) . . . . ? O5B S1B C7B C8B -160.8(11) . . . . ? N1B S1B C7B C8B 81.3(12) . . . . ? C7D S1B C7B C8B 120(4) . . . . ? O6B S1B C7B C6B 148.7(7) . . . . ? O5B S1B C7B C6B 18.8(9) . . . . ? N1B S1B C7B C6B -99.2(8) . . . . ? C7D S1B C7B C6B -61(3) . . . . ? C6B C7B C8B C9B 6(2) . . . . ? S1B C7B C8B C9B -174.7(11) . . . . ? C5B C4B C9B C8B 10.4(19) . . . . ? C3B C4B C9B C8B 175.6(12) . . . . ? C7B C8B C9B C4B -9(2) . . . . ? S1B N1B C11B C12B 154.0(3) . . . . ? S1B N1B C11B C10B -87.6(4) . . . . ? O4B C10B C11B N1B -31.9(7) . . . . ? O3B C10B C11B N1B 146.2(4) . . . . ? O4B C10B C11B C12B 88.9(6) . . . . ? O3B C10B C11B C12B -92.9(5) . . . . ? N1B C11B C12B C13B -55.5(6) . . . . ? C10B C11B C12B C13B -176.3(4) . . . . ? O2A C1A C2C C3C 24.2(8) . . . . ? O1A C1A C2C C3C 179.9(5) . . . . ? C2A C1A C2C C3C -61.1(5) . . . . ? O2A C1A C2C C3D -77.2(7) . . . . ? O1A C1A C2C C3D 78.6(7) . . . . ? C2A C1A C2C C3D -162.4(8) . . . . ? C1A C2C C3C C4C 119.1(6) . . . . ? C3D C2C C3C C4C -119.4(5) . . . . ? C1A C2C C3C C2D -117.7(5) . . . . ? C3D C2C C3C C2D 3.8(6) . . . . ? C2D C3C C4C C5C -73.0(10) . . . . ? C2C C3C C4C C5C 32.4(11) . . . . ? C2D C3C C4C C9C 99.5(7) . . . . ? C2C C3C C4C C9C -155.1(6) . . . . ? C9C C4C C5C C6C 2.2(13) . . . . ? C3C C4C C5C C6C 174.8(8) . . . . ? C4C C5C C6C C7C -9.6(15) . . . . ? C5C C6C C7C C8C 3.1(12) . . . . ? C5C C6C C7C S1A -156.1(7) . . . . ? O5A S1A C7C C6C -32.2(8) . . . . ? O6A S1A C7C C6C -161.5(7) . . . . ? C7A S1A C7C C6C 99(2) . . . . ? N1A S1A C7C C6C 84.1(7) . . . . ? O5A S1A C7C C8C 168.5(5) . . . . ? O6A S1A C7C C8C 39.2(6) . . . . ? C7A S1A C7C C8C -60.1(19) . . . . ? N1A S1A C7C C8C -75.1(6) . . . . ? C6C C7C C8C C9C 10.4(11) . . . . ? S1A C7C C8C C9C 170.8(6) . . . . ? C7C C8C C9C C4C -18.3(11) . . . . ? C5C C4C C9C C8C 12.0(11) . . . . ? C3C C4C C9C C8C -161.4(7) . . . . ? C4C C3C C2D C3D 117.6(5) . . . . ? C2C C3C C2D C3D -4.3(6) . . . . ? C4C C3C C2D C1B 4.3(8) . . . . ? C2C C3C C2D C1B -117.6(5) . . . . ? O2B C1B C2D C3D -19.1(9) . . . . ? O1B C1B C2D C3D 175.1(6) . . . . ? C2B C1B C2D C3D 57.9(8) . . . . ? O2B C1B C2D C3C 84.5(8) . . . . ? O1B C1B C2D C3C -81.3(6) . . . . ? C2B C1B C2D C3C 161.5(10) . . . . ? C3C C2D C3D C4D 120.1(7) . . . . ? C1B C2D C3D C4D -123.8(7) . . . . ? C3C C2D C3D C2C 4.2(6) . . . . ? C1B C2D C3D C2C 120.3(5) . . . . ? C1A C2C C3D C2D 112.9(6) . . . . ? C3C C2C C3D C2D -4.1(6) . . . . ? C1A C2C C3D C4D -10.6(8) . . . . ? C3C C2C C3D C4D -127.6(5) . . . . ? C2D C3D C4D C9D 164.3(8) . . . . ? C2C C3D C4D C9D -91.4(9) . . . . ? C2D C3D C4D C5D -22.9(11) . . . . ? C2C C3D C4D C5D 81.4(8) . . . . ? C9D C4D C5D C6D 6.3(10) . . . . ? C3D C4D C5D C6D -166.8(7) . . . . ? C4D C5D C6D C7D -8.5(10) . . . . ? C5D C6D C7D C8D 4.6(13) . . . . ? C5D C6D C7D S1B 173.4(5) . . . . ? O6B S1B C7D C8D -27.3(8) . . . . ? O5B S1B C7D C8D -160.4(7) . . . . ? C7B S1B C7D C8D -58(3) . . . . ? N1B S1B C7D C8D 85.2(8) . . . . ? O6B S1B C7D C6D 162.7(5) . . . . ? O5B S1B C7D C6D 29.6(7) . . . . ? C7B S1B C7D C6D 132(4) . . . . ? N1B S1B C7D C6D -84.7(6) . . . . ? C6D C7D C8D C9D 1.8(14) . . . . ? S1B C7D C8D C9D -166.9(7) . . . . ? C5D C4D C9D C8D 0.3(13) . . . . ? C3D C4D C9D C8D 173.1(8) . . . . ? C7D C8D C9D C4D -4.3(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 O1A H14A O4B 1.10 1.45 2.536(5) 169.4 . O3B H15B O2A 0.94 1.84 2.687(4) 148.5 . O3A H15A O2B 0.859(10) 1.799(11) 2.653(4) 173(3) . O1B H14B O4A 1.04 1.61 2.633(4) 168.2 . N1B H16B O6A 0.850(9) 2.120(11) 2.955(5) 167(2) 1_466 N1A H16A O6B 0.855(10) 2.29(2) 3.021(5) 144(3) 1_644 C9B H9B O5B 0.93 2.63 3.448(12) 146.5 1_545 C9A H9A O5A 0.93 2.61 3.494(10) 158.5 1_565 C5B H5B O3A 0.93 2.78 3.652(11) 157.2 1_565 C6B H6B O2B 0.93 2.96 3.685(11) 135.5 1_565 C5A H5A O3B 0.93 2.84 3.617(7) 141.2 1_545 C6A H6A O2A 0.93 2.88 3.672(8) 144.4 1_545 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.210 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.036 #== end