# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email kawheeler@eiu.edu _publ_contact_author_name 'Kraig A. Wheeler' loop_ _publ_author_name 'Kraig Wheeler' 'Steven Malehorn' 'Annie Egan' # Attachment 'web_deposit_cif_file_2_KraigA.Wheeler_1320357917.KAW108_pub.CIF' data_kaw108_DlVal(unreacted)_838809 _database_code_depnum_ccdc_archive 'CCDC 838809' #TrackingRef 'web_deposit_cif_file_2_KraigA.Wheeler_1320357917.KAW108_pub.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 N O6 S' _chemical_formula_sum 'C14 H17 N O6 S' _chemical_formula_weight 327.35 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 7.2401(1) _cell_length_b 7.2996(1) _cell_length_c 15.8742(3) _cell_angle_alpha 88.734(1) _cell_angle_beta 87.853(1) _cell_angle_gamma 64.951(1) _cell_volume 759.49(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8154 _cell_measurement_theta_min 2.759 _cell_measurement_theta_max 71.306 _exptl_crystal_description 'transparent lathe' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 2.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.459 _exptl_absorpt_correction_T_max 0.815 _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 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 15072 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 68.24 _reflns_number_total 2710 _reflns_number_gt 2566 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2010) and XPREP (Bruker, 2010) ; _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 factors. Each C-H hydrogen atom was placed in calculated positions using Uiso = 1.2 x Ueq (1.5 x Ueq for methyl groups) of the connected C atom. The remaining N-H and O-H hydrogen atoms were located in difference Fourier maps, restrained with 0.84(2) angstrom N/O-H distances, and refined using isotropic displacement parameters with Uiso = 1.2 x Ueq of the connected N/O atom. ; _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^)+(0.0528P)^2^+0.9583P] 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 2710 _refine_ls_number_parameters 211 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 0.34190(9) 0.20572(9) 0.22196(4) 0.02278(19) Uani 1 1 d . . . O1 O 0.2344(3) 1.0822(3) 0.60863(11) 0.0296(4) Uani 1 1 d D . . H15 H 0.225(5) 1.169(4) 0.6432(17) 0.036 Uiso 1 1 d D . . O2 O 0.1246(3) 0.9425(3) 0.71428(11) 0.0282(4) Uani 1 1 d . . . O3 O -0.0706(3) 0.7707(3) 0.17554(12) 0.0313(4) Uani 1 1 d D . . H16 H -0.097(5) 0.864(4) 0.2088(18) 0.038 Uiso 1 1 d D . . O4 O -0.1542(3) 0.6164(3) 0.28398(11) 0.0277(4) Uani 1 1 d . . . O5 O 0.4326(3) 0.2647(3) 0.15127(11) 0.0332(4) Uani 1 1 d . . . O6 O 0.4330(3) 0.0030(3) 0.25319(11) 0.0294(4) Uani 1 1 d . . . N1 N 0.1123(3) 0.2491(3) 0.19856(13) 0.0253(5) Uani 1 1 d D . . H1 H 0.052(4) 0.208(5) 0.2324(16) 0.030 Uiso 1 1 d D . . C1 C 0.1830(3) 0.9416(4) 0.64144(16) 0.0235(5) Uani 1 1 d . . . C2 C 0.2018(4) 0.7799(4) 0.58317(16) 0.0255(5) Uani 1 1 d . . . H2 H 0.1723 0.6717 0.6038 0.031 Uiso 1 1 calc R . . C3 C 0.2586(4) 0.7805(4) 0.50273(16) 0.0255(5) Uani 1 1 d . . . H3 H 0.2882 0.8906 0.4850 0.031 Uiso 1 1 calc R . . C4 C 0.2813(3) 0.6318(4) 0.43781(15) 0.0243(5) Uani 1 1 d . . . C5 C 0.3403(4) 0.6675(4) 0.35680(16) 0.0256(5) Uani 1 1 d . . . H5 H 0.3666 0.7830 0.3463 0.031 Uiso 1 1 calc R . . C6 C 0.3612(4) 0.5368(4) 0.29100(15) 0.0240(5) Uani 1 1 d . . . H6 H 0.3998 0.5635 0.2359 0.029 Uiso 1 1 calc R . . C7 C 0.3253(3) 0.3677(4) 0.30664(15) 0.0217(5) Uani 1 1 d . . . C8 C 0.2699(4) 0.3264(4) 0.38780(15) 0.0241(5) Uani 1 1 d . . . H8 H 0.2478 0.2085 0.3982 0.029 Uiso 1 1 calc R . . C9 C 0.2476(4) 0.4580(4) 0.45278(15) 0.0251(5) Uani 1 1 d . . . H9 H 0.2092 0.4306 0.5079 0.030 Uiso 1 1 calc R . . C10 C -0.0889(4) 0.6173(4) 0.21190(15) 0.0244(5) Uani 1 1 d . . . C11 C -0.0164(4) 0.4336(4) 0.15387(16) 0.0257(5) Uani 1 1 d . . . H11 H 0.0639 0.4550 0.1051 0.031 Uiso 1 1 calc R . . C12 C -0.2005(4) 0.4079(4) 0.12048(16) 0.0296(6) Uani 1 1 d . . . H12 H -0.2684 0.3685 0.1690 0.036 Uiso 1 1 calc R . . C13 C -0.3566(4) 0.6045(4) 0.08293(17) 0.0326(6) Uani 1 1 d . . . H13A H -0.2950 0.6436 0.0338 0.049 Uiso 1 1 calc R . . H13B H -0.3998 0.7115 0.1253 0.049 Uiso 1 1 calc R . . H13C H -0.4754 0.5846 0.0656 0.049 Uiso 1 1 calc R . . C14 C -0.1282(4) 0.2368(4) 0.05598(17) 0.0334(6) Uani 1 1 d . . . H14A H -0.2448 0.2130 0.0389 0.050 Uiso 1 1 calc R . . H14B H -0.0267 0.1132 0.0813 0.050 Uiso 1 1 calc R . . H14C H -0.0668 0.2749 0.0065 0.050 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 0.0231(3) 0.0216(3) 0.0220(3) -0.0020(2) 0.0005(2) -0.0079(2) O1 0.0336(10) 0.0283(10) 0.0232(9) -0.0030(7) -0.0001(7) -0.0095(8) O2 0.0320(9) 0.0251(9) 0.0273(10) -0.0028(7) 0.0016(7) -0.0122(8) O3 0.0393(10) 0.0248(10) 0.0297(10) -0.0061(7) 0.0024(8) -0.0134(8) O4 0.0279(9) 0.0208(9) 0.0306(10) 0.0003(7) -0.0052(7) -0.0064(7) O5 0.0375(10) 0.0362(11) 0.0269(9) -0.0058(8) 0.0050(8) -0.0169(9) O6 0.0266(9) 0.0232(9) 0.0337(10) -0.0022(7) -0.0033(7) -0.0057(7) N1 0.0276(11) 0.0209(11) 0.0265(11) -0.0005(8) -0.0026(8) -0.0092(9) C1 0.0200(11) 0.0167(12) 0.0302(13) 0.0023(10) -0.0061(10) -0.0039(9) C2 0.0239(12) 0.0214(13) 0.0292(13) 0.0014(10) -0.0037(10) -0.0075(10) C3 0.0219(12) 0.0234(13) 0.0283(13) 0.0029(10) -0.0044(9) -0.0066(10) C4 0.0192(11) 0.0218(12) 0.0265(12) -0.0008(10) -0.0044(9) -0.0030(9) C5 0.0249(12) 0.0202(12) 0.0295(13) 0.0005(10) -0.0026(10) -0.0075(10) C6 0.0224(12) 0.0246(13) 0.0234(12) 0.0001(10) -0.0004(9) -0.0084(10) C7 0.0192(11) 0.0204(12) 0.0222(12) -0.0014(9) -0.0022(9) -0.0049(9) C8 0.0220(11) 0.0227(12) 0.0266(12) 0.0035(10) -0.0033(9) -0.0086(10) C9 0.0205(11) 0.0300(13) 0.0193(11) 0.0011(10) -0.0004(9) -0.0052(10) C10 0.0220(11) 0.0223(13) 0.0242(12) 0.0003(10) -0.0062(9) -0.0045(10) C11 0.0278(12) 0.0219(13) 0.0253(12) 0.0001(10) -0.0023(10) -0.0084(10) C12 0.0306(13) 0.0303(14) 0.0251(13) -0.0025(10) -0.0021(10) -0.0100(11) C13 0.0319(14) 0.0297(14) 0.0308(14) -0.0026(11) -0.0093(11) -0.0070(11) C14 0.0404(15) 0.0276(14) 0.0276(13) -0.0038(11) -0.0066(11) -0.0093(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 O6 1.4270(19) . ? S1 O5 1.4279(19) . ? S1 N1 1.612(2) . ? S1 C7 1.777(2) . ? O1 C1 1.322(3) . ? O1 H15 0.828(18) . ? O2 C1 1.215(3) . ? O3 C10 1.302(3) . ? O3 H16 0.822(18) . ? O4 C10 1.223(3) . ? N1 C11 1.459(3) . ? N1 H1 0.812(17) . ? C1 C2 1.474(3) . ? C2 C3 1.327(4) . ? C2 H2 0.9500 . ? C3 C4 1.467(4) . ? C3 H3 0.9500 . ? C4 C5 1.394(4) . ? C4 C9 1.404(4) . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 C7 1.381(4) . ? C6 H6 0.9500 . ? C7 C8 1.399(3) . ? C8 C9 1.383(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.531(3) . ? C11 C12 1.537(4) . ? C11 H11 1.0000 . ? C12 C13 1.527(4) . ? C12 C14 1.531(4) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 S1 O5 120.22(11) . . ? O6 S1 N1 106.24(11) . . ? O5 S1 N1 107.83(11) . . ? O6 S1 C7 107.37(11) . . ? O5 S1 C7 107.20(12) . . ? N1 S1 C7 107.39(11) . . ? C1 O1 H15 113(2) . . ? C10 O3 H16 111(2) . . ? C11 N1 S1 120.85(18) . . ? C11 N1 H1 115(2) . . ? S1 N1 H1 116(2) . . ? O2 C1 O1 123.4(2) . . ? O2 C1 C2 121.4(2) . . ? O1 C1 C2 115.2(2) . . ? C3 C2 C1 122.1(2) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C2 C3 C4 127.9(3) . . ? C2 C3 H3 116.0 . . ? C4 C3 H3 116.0 . . ? C5 C4 C9 118.8(2) . . ? C5 C4 C3 117.2(2) . . ? C9 C4 C3 123.9(2) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 119.3(2) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 120.7(2) . . ? C6 C7 S1 119.45(18) . . ? C8 C7 S1 119.85(19) . . ? C9 C8 C7 119.7(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C4 120.4(2) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? O4 C10 O3 124.9(2) . . ? O4 C10 C11 123.1(2) . . ? O3 C10 C11 112.0(2) . . ? N1 C11 C10 111.0(2) . . ? N1 C11 C12 108.7(2) . . ? C10 C11 C12 110.1(2) . . ? N1 C11 H11 109.0 . . ? C10 C11 H11 109.0 . . ? C12 C11 H11 109.0 . . ? C13 C12 C14 111.1(2) . . ? C13 C12 C11 111.8(2) . . ? C14 C12 C11 109.9(2) . . ? C13 C12 H12 108.0 . . ? C14 C12 H12 108.0 . . ? C11 C12 H12 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 S1 N1 C11 -171.51(18) . . . . ? O5 S1 N1 C11 -41.4(2) . . . . ? C7 S1 N1 C11 73.8(2) . . . . ? O2 C1 C2 C3 177.6(2) . . . . ? O1 C1 C2 C3 -2.5(3) . . . . ? C1 C2 C3 C4 -179.2(2) . . . . ? C2 C3 C4 C5 179.0(2) . . . . ? C2 C3 C4 C9 -1.1(4) . . . . ? C9 C4 C5 C6 1.5(3) . . . . ? C3 C4 C5 C6 -178.6(2) . . . . ? C4 C5 C6 C7 -0.8(4) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C5 C6 C7 S1 177.50(18) . . . . ? O6 S1 C7 C6 141.82(19) . . . . ? O5 S1 C7 C6 11.4(2) . . . . ? N1 S1 C7 C6 -104.3(2) . . . . ? O6 S1 C7 C8 -40.2(2) . . . . ? O5 S1 C7 C8 -170.62(18) . . . . ? N1 S1 C7 C8 73.7(2) . . . . ? C6 C7 C8 C9 1.1(3) . . . . ? S1 C7 C8 C9 -176.90(18) . . . . ? C7 C8 C9 C4 -0.4(3) . . . . ? C5 C4 C9 C8 -0.9(3) . . . . ? C3 C4 C9 C8 179.2(2) . . . . ? S1 N1 C11 C10 -73.3(2) . . . . ? S1 N1 C11 C12 165.38(17) . . . . ? O4 C10 C11 N1 -44.8(3) . . . . ? O3 C10 C11 N1 134.6(2) . . . . ? O4 C10 C11 C12 75.6(3) . . . . ? O3 C10 C11 C12 -105.0(2) . . . . ? N1 C11 C12 C13 172.5(2) . . . . ? C10 C11 C12 C13 50.7(3) . . . . ? N1 C11 C12 C14 -63.6(3) . . . . ? C10 C11 C12 C14 174.6(2) . . . . ? 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 H15 O4 0.828(18) 1.844(19) 2.663(2) 170(3) 2_576 O3 H16 O2 0.822(18) 1.830(19) 2.648(2) 173(3) 2_576 N1 H1 O2 0.812(17) 2.15(2) 2.929(3) 162(3) 2_566 C5 H5 O6 0.95 2.34 3.207(3) 150.9 1_565 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.635 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.066 # Attachment 'web_deposit_cif_file_1_KraigA.Wheeler_1320357917.KAW108C_pub.CIF' data_kaw108c_DLVal(reacted)_838810 _database_code_depnum_ccdc_archive 'CCDC 838810' #TrackingRef 'web_deposit_cif_file_1_KraigA.Wheeler_1320357917.KAW108C_pub.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H34 N2 O12 S2' _chemical_formula_sum 'C28 H34 N2 O12 S2' _chemical_formula_weight 654.71 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 7.4391(3) _cell_length_b 7.6719(3) _cell_length_c 15.0529(7) _cell_angle_alpha 88.371(3) _cell_angle_beta 85.421(3) _cell_angle_gamma 61.552(2) _cell_volume 752.91(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5530 _cell_measurement_theta_min 2.745 _cell_measurement_theta_max 61.404 _exptl_crystal_description 'transparent lathe' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 2.188 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.459 _exptl_absorpt_correction_T_max 0.815 _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 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13224 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0427 _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 -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 66.77 _reflns_number_total 2563 _reflns_number_gt 2133 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2010) and XPREP (Bruker, 2010) ; _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 factors. Each C-H hydrogen atom was placed in calculated positions using Uiso = 1.2 x Ueq (1.5 x Ueq for methyl groups) of the connected C atom. The remaining N-H and O-H hydorgen atoms were located in difference Fourier maps and refined with Uiso = 1.2 x Ueq of the connected N/O atom. The OH hydrogen atoms were further placed in idealized positions with O-H distances of 0.84 angstroms. Reaction conversion was determined by refined the occupancy factors of the reactant and product phases. The phenyl groups of the reactant phase were constrained to similar photoproduct phenyl geometries using the Shelx SAME command. ; _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^)+(0.0915P)^2^+1.4892P] 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 2563 _refine_ls_number_parameters 264 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0751 _refine_ls_wR_factor_ref 0.2093 _refine_ls_wR_factor_gt 0.1959 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.154 _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 0.96180(17) 0.20338(14) 0.26786(8) 0.0401(4) Uani 1 1 d . . . O1 O 0.1698(6) 1.0837(5) -0.0930(2) 0.0518(9) Uani 1 1 d . . . H1 H 0.0900 1.1502 -0.1319 0.062 Uiso 1 1 calc R . . O2 O 0.3990(5) 0.9496(4) -0.2082(2) 0.0490(8) Uani 1 1 d . . . O3 O 0.8406(5) 0.7661(4) 0.3231(2) 0.0456(8) Uani 1 1 d . . . H14 H 0.7797 0.8572 0.2870 0.055 Uiso 1 1 calc R . . O4 O 1.0631(5) 0.6223(4) 0.20506(19) 0.0431(8) Uani 1 1 d . . . O5 O 0.8379(5) 0.2283(5) 0.3470(2) 0.0546(9) Uani 1 1 d . . . O6 O 1.0671(5) 0.0159(5) 0.2236(3) 0.0612(10) Uani 1 1 d . . . N1 N 1.1407(6) 0.2559(5) 0.2897(3) 0.0386(9) Uani 1 1 d . . . H4 H 1.245(8) 0.217(8) 0.252(3) 0.046 Uiso 1 1 d . . . C1 C 0.3536(7) 0.9708(7) -0.1315(4) 0.0461(11) Uani 1 1 d . . . C2 C 0.5135(10) 0.9212(9) -0.0628(4) 0.0391(18) Uani 0.664(10) 1 d P . 1 H2 H 0.6472 0.8054 -0.0834 0.047 Uiso 0.664(10) 1 calc PR . 1 C3 C 0.4542(10) 0.8979(10) 0.0354(5) 0.0396(19) Uani 0.664(10) 1 d P . 1 H3 H 0.3051 0.9366 0.0431 0.048 Uiso 0.664(10) 1 calc PR . 1 C4 C 0.5763(11) 0.7054(13) 0.0830(5) 0.0364(19) Uani 0.664(10) 1 d PD . 1 C5 C 0.514(2) 0.7013(19) 0.1710(7) 0.039(3) Uani 0.664(10) 1 d PD . 1 H5 H 0.3886 0.8074 0.1947 0.046 Uiso 0.664(10) 1 calc PR . 1 C6 C 0.628(3) 0.548(2) 0.2259(9) 0.039(4) Uani 0.664(10) 1 d PD . 1 H6 H 0.5888 0.5540 0.2878 0.046 Uiso 0.664(10) 1 calc PR . 1 C7 C 0.803(2) 0.385(2) 0.1892(7) 0.030(4) Uani 0.664(10) 1 d PD . 1 C8 C 0.8648(13) 0.3791(15) 0.0996(5) 0.039(2) Uani 0.664(10) 1 d PD . 1 H8 H 0.9842 0.2676 0.0747 0.047 Uiso 0.664(10) 1 calc PR . 1 C9 C 0.7485(13) 0.5396(15) 0.0468(5) 0.040(2) Uani 0.664(10) 1 d PD . 1 H9 H 0.7873 0.5357 -0.0151 0.048 Uiso 0.664(10) 1 calc PR . 1 C10 C 0.9970(7) 0.6192(6) 0.2812(3) 0.0333(9) Uani 1 1 d . . . C11 C 1.0959(7) 0.4336(6) 0.3388(3) 0.0362(9) Uani 1 1 d . . . H11 H 0.9979 0.4486 0.3912 0.043 Uiso 1 1 calc R . . C12 C 1.2951(7) 0.4108(6) 0.3734(3) 0.0393(10) Uani 1 1 d . . . H12 H 1.3987 0.3784 0.3214 0.047 Uiso 1 1 calc R . . C13 C 1.2606(8) 0.6037(7) 0.4156(3) 0.0481(12) Uani 1 1 d . . . H13A H 1.1570 0.6402 0.4660 0.072 Uiso 1 1 calc R . . H13B H 1.2132 0.7092 0.3712 0.072 Uiso 1 1 calc R . . H13C H 1.3895 0.5858 0.4368 0.072 Uiso 1 1 calc R . . C14 C 1.3793(8) 0.2408(7) 0.4386(3) 0.0493(12) Uani 1 1 d . . . H14A H 1.5131 0.2189 0.4552 0.074 Uiso 1 1 calc R . . H14B H 1.3946 0.1202 0.4106 0.074 Uiso 1 1 calc R . . H14C H 1.2844 0.2735 0.4921 0.074 Uiso 1 1 calc R . . C2A C 0.499(3) 0.779(2) -0.0770(12) 0.058(5) Uani 0.336(10) 1 d P . 2 H2A H 0.6175 0.6735 -0.1062 0.070 Uiso 0.336(10) 1 calc PR . 2 C3A C 0.456(3) 0.770(3) 0.0033(13) 0.062(5) Uani 0.336(10) 1 d P . 2 H3A H 0.3271 0.8707 0.0273 0.075 Uiso 0.336(10) 1 calc PR . 2 C4A C 0.584(2) 0.618(3) 0.0654(13) 0.048(5) Uani 0.336(10) 1 d PD . 2 C5A C 0.523(5) 0.650(4) 0.1550(15) 0.060(11) Uani 0.336(10) 1 d PD . 2 H5A H 0.3983 0.7635 0.1734 0.071 Uiso 0.336(10) 1 calc PR . 2 C6A C 0.638(6) 0.522(5) 0.2183(15) 0.038(11) Uiso 0.336(10) 1 d PD . 2 H6A H 0.5864 0.5448 0.2791 0.046 Uiso 0.336(10) 1 calc PR . 2 C7A C 0.827(5) 0.359(5) 0.1956(12) 0.036(10) Uiso 0.336(10) 1 d PD . 2 C8A C 0.885(3) 0.314(3) 0.1049(11) 0.037(6) Uiso 0.336(10) 1 d PD . 2 H8A H 1.0048 0.1948 0.0868 0.044 Uiso 0.336(10) 1 calc PR . 2 C9A C 0.765(3) 0.443(3) 0.0415(11) 0.048(5) Uani 0.336(10) 1 d PD . 2 H9A H 0.8063 0.4120 -0.0199 0.058 Uiso 0.336(10) 1 calc PR . 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 0.0435(7) 0.0242(5) 0.0552(7) 0.0055(4) -0.0147(5) -0.0168(5) O1 0.078(3) 0.055(2) 0.0401(17) 0.0128(15) -0.0220(17) -0.044(2) O2 0.059(2) 0.0298(16) 0.052(2) 0.0015(14) -0.0187(16) -0.0141(15) O3 0.0487(19) 0.0280(15) 0.0523(19) 0.0036(13) -0.0085(15) -0.0115(15) O4 0.057(2) 0.0313(15) 0.0396(17) 0.0001(12) -0.0070(14) -0.0199(15) O5 0.058(2) 0.053(2) 0.059(2) 0.0204(16) -0.0159(17) -0.0309(18) O6 0.051(2) 0.0264(16) 0.103(3) -0.0056(17) -0.025(2) -0.0131(16) N1 0.039(2) 0.0261(17) 0.046(2) -0.0004(15) -0.0081(16) -0.0111(17) C1 0.035(3) 0.032(2) 0.067(3) 0.003(2) -0.004(2) -0.012(2) C2 0.038(4) 0.027(3) 0.044(4) -0.003(3) -0.006(3) -0.008(3) C3 0.033(4) 0.031(4) 0.050(4) 0.001(3) -0.005(3) -0.012(3) C4 0.033(4) 0.027(4) 0.054(5) 0.005(3) -0.015(3) -0.017(3) C5 0.029(5) 0.025(6) 0.054(5) 0.003(4) -0.006(4) -0.006(4) C6 0.038(7) 0.021(5) 0.051(7) 0.000(4) 0.002(3) -0.011(4) C7 0.026(6) 0.018(5) 0.043(6) 0.008(3) -0.019(4) -0.006(4) C8 0.041(5) 0.025(4) 0.042(5) -0.001(4) -0.009(3) -0.008(4) C9 0.051(6) 0.041(5) 0.032(4) 0.005(4) -0.011(3) -0.024(5) C10 0.045(2) 0.029(2) 0.031(2) -0.0011(16) -0.0086(18) -0.021(2) C11 0.040(2) 0.028(2) 0.038(2) -0.0003(17) -0.0051(18) -0.0149(19) C12 0.043(3) 0.041(2) 0.039(2) 0.0027(18) -0.0077(19) -0.023(2) C13 0.057(3) 0.049(3) 0.042(2) -0.005(2) -0.012(2) -0.027(2) C14 0.051(3) 0.050(3) 0.047(3) 0.011(2) -0.017(2) -0.023(2) C2A 0.054(10) 0.050(10) 0.079(12) -0.024(8) 0.004(8) -0.032(8) C3A 0.073(12) 0.067(11) 0.076(12) 0.004(9) -0.012(9) -0.056(10) C4A 0.039(10) 0.033(10) 0.088(14) 0.029(9) -0.036(9) -0.027(9) C5A 0.053(14) 0.028(14) 0.09(2) 0.001(11) -0.010(13) -0.015(10) C9A 0.059(11) 0.046(11) 0.045(9) 0.007(9) -0.020(8) -0.028(10) _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 1.405(4) . ? S1 O6 1.423(3) . ? S1 C7A 1.61(2) . ? S1 N1 1.622(4) . ? S1 C7 1.817(12) . ? O1 C1 1.315(6) . ? O1 H1 0.8400 . ? O2 C1 1.171(6) . ? O3 C10 1.302(5) . ? O3 H14 0.8400 . ? O4 C10 1.215(5) . ? N1 C11 1.450(5) . ? N1 H4 0.86(5) . ? C1 C2 1.540(8) . ? C1 C2A 1.602(19) . ? C2 C3 1.538(9) . ? C2 C3 1.587(9) 2_675 ? C2 H2 1.0000 . ? C3 C4 1.512(10) . ? C3 C2 1.587(9) 2_675 ? C3 H3 1.0000 . ? C4 C5 1.371(12) . ? C4 C9 1.390(12) . ? C5 C6 1.374(10) . ? C5 H5 0.9500 . ? C6 C7 1.392(11) . ? C6 H6 0.9500 . ? C7 C8 1.383(10) . ? C8 C9 1.392(11) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.534(5) . ? C11 C12 1.539(6) . ? C11 H11 1.0000 . ? C12 C14 1.518(6) . ? C12 C13 1.525(6) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C2A C3A 1.23(2) . ? C2A H2A 0.9500 . ? C3A C4A 1.47(2) . ? C3A H3A 0.9500 . ? C4A C5A 1.378(17) . ? C4A C9A 1.405(17) . ? C5A C6A 1.370(16) . ? C5A H5A 0.9500 . ? C6A C7A 1.388(16) . ? C6A H6A 0.9500 . ? C7A C8A 1.402(15) . ? C8A C9A 1.389(16) . ? 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 120.5(2) . . ? O5 S1 C7A 109.1(9) . . ? O6 S1 C7A 106.3(10) . . ? O5 S1 N1 107.8(2) . . ? O6 S1 N1 104.8(2) . . ? C7A S1 N1 107.6(15) . . ? O5 S1 C7 107.3(4) . . ? O6 S1 C7 108.1(4) . . ? N1 S1 C7 107.7(6) . . ? C1 O1 H1 109.5 . . ? C10 O3 H14 109.5 . . ? C11 N1 S1 121.8(3) . . ? C11 N1 H4 114(3) . . ? S1 N1 H4 117(3) . . ? O2 C1 O1 126.5(5) . . ? O2 C1 C2 122.1(5) . . ? O1 C1 C2 108.9(5) . . ? O2 C1 C2A 111.8(7) . . ? O1 C1 C2A 115.8(7) . . ? C3 C2 C1 118.6(5) . . ? C3 C2 C3 89.7(5) . 2_675 ? C1 C2 C3 114.7(5) . 2_675 ? C3 C2 H2 110.8 . . ? C1 C2 H2 110.7 . . ? C3 C2 H2 110.8 2_675 . ? C4 C3 C2 120.3(6) . . ? C4 C3 C2 115.9(6) . 2_675 ? C2 C3 C2 90.3(5) . 2_675 ? C4 C3 H3 109.6 . . ? C2 C3 H3 109.6 . . ? C2 C3 H3 109.6 2_675 . ? C5 C4 C9 118.3(8) . . ? C5 C4 C3 115.8(8) . . ? C9 C4 C3 125.8(7) . . ? C4 C5 C6 122.0(10) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C6 C7 118.7(10) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 120.8(11) . . ? C8 C7 S1 122.6(8) . . ? C6 C7 S1 116.0(8) . . ? C7 C8 C9 118.7(8) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C4 C9 C8 121.1(7) . . ? C4 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? O4 C10 O3 125.7(4) . . ? O4 C10 C11 121.6(4) . . ? O3 C10 C11 112.7(3) . . ? N1 C11 C10 111.6(3) . . ? N1 C11 C12 109.2(4) . . ? C10 C11 C12 110.7(3) . . ? N1 C11 H11 108.4 . . ? C10 C11 H11 108.4 . . ? C12 C11 H11 108.4 . . ? C14 C12 C13 111.2(4) . . ? C14 C12 C11 110.3(4) . . ? C13 C12 C11 111.0(4) . . ? C14 C12 H12 108.0 . . ? C13 C12 H12 108.0 . . ? C11 C12 H12 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3A C2A C1 119.3(15) . . ? C3A C2A H2A 120.4 . . ? C1 C2A H2A 120.4 . . ? C2A C3A C4A 126(2) . . ? C2A C3A H3A 116.8 . . ? C4A C3A H3A 116.8 . . ? C5A C4A C9A 116.7(14) . . ? C5A C4A C3A 117.7(18) . . ? C9A C4A C3A 125.6(17) . . ? C6A C5A C4A 122.0(18) . . ? C6A C5A H5A 119.0 . . ? C4A C5A H5A 119.0 . . ? C5A C6A C7A 121.4(18) . . ? C5A C6A H6A 119.3 . . ? C7A C6A H6A 119.3 . . ? C6A C7A C8A 117.7(18) . . ? C6A C7A S1 122.7(15) . . ? C8A C7A S1 118.8(17) . . ? C9A C8A C7A 119.6(16) . . ? C9A C8A H8A 120.2 . . ? C7A C8A H8A 120.2 . . ? C8A C9A C4A 121.9(14) . . ? C8A C9A H9A 119.0 . . ? C4A C9A H9A 119.0 . . ? 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 -47.6(4) . . . . ? O6 S1 N1 C11 -177.2(3) . . . . ? C7A S1 N1 C11 69.9(9) . . . . ? C7 S1 N1 C11 67.9(5) . . . . ? O2 C1 C2 C3 -163.4(5) . . . . ? O1 C1 C2 C3 33.3(7) . . . . ? C2A C1 C2 C3 -74.7(10) . . . . ? O2 C1 C2 C3 92.5(6) . . . 2_675 ? O1 C1 C2 C3 -70.8(6) . . . 2_675 ? C2A C1 C2 C3 -178.8(12) . . . 2_675 ? C1 C2 C3 C4 121.1(7) . . . . ? C3 C2 C3 C4 -120.6(7) 2_675 . . . ? C1 C2 C3 C2 -118.2(6) . . . 2_675 ? C3 C2 C3 C2 0.0 2_675 . . 2_675 ? C2 C3 C4 C5 178.4(9) . . . . ? C2 C3 C4 C5 71.5(11) 2_675 . . . ? C2 C3 C4 C9 1.7(11) . . . . ? C2 C3 C4 C9 -105.2(9) 2_675 . . . ? C9 C4 C5 C6 7(2) . . . . ? C3 C4 C5 C6 -170.0(16) . . . . ? C4 C5 C6 C7 -5(3) . . . . ? C5 C6 C7 C8 2(3) . . . . ? C5 C6 C7 S1 173.1(16) . . . . ? O5 S1 C7 C8 -167.8(11) . . . . ? O6 S1 C7 C8 -36.4(14) . . . . ? N1 S1 C7 C8 76.4(13) . . . . ? O5 S1 C7 C6 21.1(18) . . . . ? O6 S1 C7 C6 152.6(16) . . . . ? N1 S1 C7 C6 -94.7(16) . . . . ? C6 C7 C8 C9 0(2) . . . . ? S1 C7 C8 C9 -170.6(9) . . . . ? C5 C4 C9 C8 -4.9(14) . . . . ? C3 C4 C9 C8 171.8(8) . . . . ? C7 C8 C9 C4 1.5(15) . . . . ? S1 N1 C11 C10 -74.6(4) . . . . ? S1 N1 C11 C12 162.8(3) . . . . ? O4 C10 C11 N1 -45.0(5) . . . . ? O3 C10 C11 N1 135.3(4) . . . . ? O4 C10 C11 C12 76.8(5) . . . . ? O3 C10 C11 C12 -103.0(4) . . . . ? N1 C11 C12 C14 -63.2(5) . . . . ? C10 C11 C12 C14 173.6(4) . . . . ? N1 C11 C12 C13 173.0(4) . . . . ? C10 C11 C12 C13 49.9(5) . . . . ? O2 C1 C2A C3A -171.7(11) . . . . ? O1 C1 C2A C3A -16.8(15) . . . . ? C2 C1 C2A C3A 74.1(13) . . . . ? C1 C2A C3A C4A -172.0(13) . . . . ? C2A C3A C4A C5A 170(2) . . . . ? C2A C3A C4A C9A -9(3) . . . . ? C9A C4A C5A C6A 3(5) . . . . ? C3A C4A C5A C6A -177(3) . . . . ? C4A C5A C6A C7A 4(7) . . . . ? C5A C6A C7A C8A -9(7) . . . . ? C5A C6A C7A S1 -178(4) . . . . ? O5 S1 C7A C6A 15(5) . . . . ? O6 S1 C7A C6A 147(4) . . . . ? N1 S1 C7A C6A -101(4) . . . . ? O5 S1 C7A C8A -154(3) . . . . ? O6 S1 C7A C8A -22(3) . . . . ? N1 S1 C7A C8A 89(3) . . . . ? C6A C7A C8A C9A 8(5) . . . . ? S1 C7A C8A C9A 177(2) . . . . ? C5A C4A C9A C8A -4(3) . . . . ? C3A C4A C9A C8A 175.6(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O4 0.84 1.94 2.732(4) 157.3 2_675 O3 H14 O2 0.84 1.91 2.738(4) 169.1 2_675 N1 H4 O2 0.86(5) 2.37(5) 3.164(5) 154(5) 2_765 C5 H5 O6 0.95 2.17 3.092(12) 164.1 1_465 C5A H5A O6 0.95 2.37 3.32(3) 171.8 1_465 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 66.77 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.606 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.095 # Attachment 'web_deposit_cif_file_3_KraigA.Wheeler_1320357917.kaw73_pub.CIF' data_twin5-kaw73_DVal(unreacted)_838811 _database_code_depnum_ccdc_archive 'CCDC 838811' #TrackingRef 'web_deposit_cif_file_3_KraigA.Wheeler_1320357917.kaw73_pub.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 N O6 S' _chemical_formula_sum 'C14 H17 N O6 S' _chemical_formula_weight 327.35 _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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.9008(2) _cell_length_b 8.0121(2) _cell_length_c 11.8061(3) _cell_angle_alpha 83.617(1) _cell_angle_beta 77.774(2) _cell_angle_gamma 88.744(2) _cell_volume 725.87(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7614 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 67.57 _exptl_crystal_description 'transparent rhomboid' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 2.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4076 _exptl_absorpt_correction_T_max 0.6908 _exptl_absorpt_process_details 'TWINABS (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_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 4857 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 67.94 _reflns_number_total 4857 _reflns_number_gt 4664 _reflns_threshold_expression >2sigma(I) _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. The data were collected as a two component twin (63:37 ratio) and scaled using Twinabs. The structure was solved using reflections from the strongest component via hklf4 format and refined using both components in hklf5 format. Though the assigned space group is triclinic P1, Platon/ADDSYM detects additional (pseudo)symmetry. The output form this excercise suggests space group P-1. The extra detected symmetry is an artifact of the engineered supramolecular motifs contained in the structure. Though approximate inversion symmetry describes these motifs, they are rigorously noncentrosymmetric given tha tboth components possess R configuration. All nonhydrogen atoms were located in a single difference Fourier electron denisty map and refined using anisotropic displacement parameters. The N-H and O-H hydrogen atoms were located in difference density maps; the O-H hydrogen atoms were constrained to 0.84(2) angstroms. All other hydrogen atoms were placed in idealized positions with Uiso = 1.2 x Ueq (1.5 x Ueq for methyl groups) of the attached atom. ; _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^)+(0.0573P)^2^+0.8238P] 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 0.54(6) _refine_ls_number_reflns 2538 _refine_ls_number_parameters 410 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.081 _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 -0.03049(15) -0.27919(13) 1.28408(14) 0.0216(3) Uani 1 1 d . . . O1A O 0.4295(5) 0.6450(5) 0.8793(3) 0.0276(9) Uani 1 1 d . . . H15A H 0.4841 0.7292 0.8413 0.033 Uiso 1 1 calc R . . O2A O 0.6289(5) 0.5066(5) 0.7597(3) 0.0267(8) Uani 1 1 d . . . O3A O 0.2207(5) 0.0433(5) 1.4032(3) 0.0273(8) Uani 1 1 d . . . H16A H 0.2757 0.1302 1.3705 0.033 Uiso 1 1 calc R . . O4A O 0.4329(5) -0.0819(4) 1.2859(3) 0.0266(8) Uani 1 1 d . . . O5A O -0.2148(5) -0.2670(5) 1.3134(3) 0.0265(8) Uani 1 1 d . . . O6A O 0.0515(5) -0.4208(4) 1.2340(3) 0.0274(9) Uani 1 1 d . . . N1A N 0.0312(6) -0.2624(5) 1.4048(4) 0.0229(9) Uani 1 1 d D . . C1A C 0.5008(7) 0.5085(7) 0.8401(5) 0.0226(11) Uani 1 1 d . . . C2A C 0.4194(7) 0.3496(7) 0.8981(5) 0.0251(12) Uani 1 1 d . . . H2A H 0.4647 0.2481 0.8693 0.030 Uiso 1 1 calc R . . C3A C 0.2863(8) 0.3397(7) 0.9886(5) 0.0255(12) Uani 1 1 d . . . H3A H 0.2401 0.4429 1.0140 0.031 Uiso 1 1 calc R . . C4A C 0.2035(7) 0.1860(7) 1.0531(5) 0.0224(12) Uani 1 1 d . . . C5A C 0.0610(7) 0.1984(7) 1.1440(5) 0.0247(12) Uani 1 1 d . . . H5A H 0.0157 0.3060 1.1602 0.030 Uiso 1 1 calc R . . C6A C -0.0155(7) 0.0572(7) 1.2108(5) 0.0234(11) Uani 1 1 d . . . H6A H -0.1135 0.0668 1.2722 0.028 Uiso 1 1 calc R . . C7A C 0.0532(7) -0.1004(6) 1.1868(5) 0.0196(11) Uani 1 1 d . . . C8A C 0.1894(7) -0.1157(7) 1.0949(5) 0.0238(11) Uani 1 1 d . . . H8A H 0.2323 -0.2239 1.0781 0.029 Uiso 1 1 calc R . . C9A C 0.2645(7) 0.0258(7) 1.0269(5) 0.0256(12) Uani 1 1 d . . . H9A H 0.3573 0.0147 0.9622 0.031 Uiso 1 1 calc R . . C10A C 0.2953(7) -0.0849(6) 1.3608(4) 0.0202(10) Uani 1 1 d . . . C11A C 0.2121(7) -0.2554(6) 1.4109(4) 0.0208(10) Uani 1 1 d . . . H11A H 0.2760 -0.3436 1.3651 0.025 Uiso 1 1 calc R . . C12A C 0.2318(7) -0.2929(7) 1.5386(5) 0.0237(12) Uani 1 1 d . . . H12A H 0.1629 -0.2075 1.5845 0.028 Uiso 1 1 calc R . . C13A C 0.4213(8) -0.2760(8) 1.5470(5) 0.0354(14) Uani 1 1 d . . . H13A H 0.4923 -0.3560 1.5004 0.053 Uiso 1 1 calc R . . H13B H 0.4312 -0.2998 1.6286 0.053 Uiso 1 1 calc R . . H13C H 0.4618 -0.1615 1.5175 0.053 Uiso 1 1 calc R . . C14A C 0.1617(8) -0.4645(7) 1.5912(5) 0.0285(12) Uani 1 1 d . . . H14A H 0.1792 -0.4858 1.6712 0.043 Uiso 1 1 calc R . . H14B H 0.2226 -0.5501 1.5447 0.043 Uiso 1 1 calc R . . H14C H 0.0376 -0.4690 1.5917 0.043 Uiso 1 1 calc R . . S1B S 0.98299(14) 1.15932(13) 0.79131(14) 0.0203(3) Uani 1 1 d . . . O1B O 0.5776(6) 0.2086(5) 1.1903(4) 0.0354(10) Uani 1 1 d . . . H15B H 0.5255 0.1231 1.2283 0.043 Uiso 1 1 calc R . . O2B O 0.3749(5) 0.3365(5) 1.3121(4) 0.0322(9) Uani 1 1 d . . . O3B O 0.7815(5) 0.7813(4) 0.6365(3) 0.0241(8) Uani 1 1 d . . . H16B H 0.7242 0.6974 0.6724 0.029 Uiso 1 1 calc R . . O4B O 0.6042(5) 0.9183(4) 0.7705(3) 0.0233(8) Uani 1 1 d . . . O5B O 1.1445(5) 1.1238(5) 0.7201(3) 0.0272(8) Uani 1 1 d . . . O6B O 0.9618(5) 1.2988(4) 0.8598(3) 0.0266(8) Uani 1 1 d . . . N1B N 0.8427(6) 1.1931(5) 0.7076(4) 0.0213(9) Uani 1 1 d D . . C1B C 0.5044(7) 0.3401(7) 1.2289(5) 0.0221(11) Uani 1 1 d . . . C2B C 0.5775(7) 0.5048(7) 1.1729(5) 0.0263(12) Uani 1 1 d . . . H2B H 0.5295 0.6036 1.2044 0.032 Uiso 1 1 calc R . . C3B C 0.7070(7) 0.5201(7) 1.0807(5) 0.0242(11) Uani 1 1 d . . . H3B H 0.7571 0.4193 1.0534 0.029 Uiso 1 1 calc R . . C4B C 0.7808(7) 0.6804(7) 1.0163(5) 0.0214(11) Uani 1 1 d . . . C5B C 0.9217(7) 0.6763(7) 0.9230(5) 0.0239(11) Uani 1 1 d . . . H5B H 0.9723 0.5716 0.9042 0.029 Uiso 1 1 calc R . . C6B C 0.9884(7) 0.8231(7) 0.8577(5) 0.0216(11) Uani 1 1 d . . . H6B H 1.0855 0.8200 0.7948 0.026 Uiso 1 1 calc R . . C7B C 0.9124(7) 0.9740(7) 0.8850(5) 0.0215(11) Uani 1 1 d . . . C8B C 0.7752(7) 0.9830(7) 0.9790(5) 0.0231(11) Uani 1 1 d . . . H8B H 0.7269 1.0886 0.9979 0.028 Uiso 1 1 calc R . . C9B C 0.7097(7) 0.8370(7) 1.0447(5) 0.0224(11) Uani 1 1 d . . . H9B H 0.6160 0.8418 1.1097 0.027 Uiso 1 1 calc R . . C10B C 0.7240(6) 0.9185(6) 0.6873(4) 0.0197(10) Uani 1 1 d . . . C11B C 0.8231(7) 1.0745(6) 0.6260(4) 0.0216(10) Uani 1 1 d . . . H11B H 0.9416 1.0387 0.5879 0.026 Uiso 1 1 calc R . . C12B C 0.7326(7) 1.1542(7) 0.5287(5) 0.0256(12) Uani 1 1 d . . . H12B H 0.7288 1.0666 0.4752 0.031 Uiso 1 1 calc R . . C13B C 0.5472(7) 1.2072(7) 0.5739(5) 0.0300(12) Uani 1 1 d . . . H13D H 0.4937 1.2457 0.5079 0.045 Uiso 1 1 calc R . . H13E H 0.5463 1.2987 0.6226 0.045 Uiso 1 1 calc R . . H13F H 0.4818 1.1114 0.6203 0.045 Uiso 1 1 calc R . . C14B C 0.8366(8) 1.3014(7) 0.4564(5) 0.0297(12) Uani 1 1 d . . . H14D H 0.8366 1.3931 0.5049 0.045 Uiso 1 1 calc R . . H14E H 0.7841 1.3403 0.3900 0.045 Uiso 1 1 calc R . . H14F H 0.9559 1.2656 0.4278 0.045 Uiso 1 1 calc R . . H17A H -0.046(5) -0.221(6) 1.453(4) 0.015(13) Uiso 1 1 d D . . H17B H 0.756(5) 1.250(6) 0.732(4) 0.009(12) Uiso 1 1 d 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 0.0268(7) 0.0177(6) 0.0202(6) -0.0018(5) -0.0045(5) -0.0074(5) O1A 0.030(2) 0.0197(19) 0.029(2) -0.0028(16) 0.0039(16) -0.0052(15) O2A 0.026(2) 0.0204(19) 0.031(2) -0.0019(15) -0.0012(16) -0.0032(15) O3A 0.030(2) 0.0184(19) 0.031(2) -0.0026(16) -0.0017(15) -0.0079(15) O4A 0.0238(19) 0.026(2) 0.0266(19) -0.0044(15) 0.0038(15) -0.0044(14) O5A 0.029(2) 0.0264(19) 0.0233(18) 0.0013(15) -0.0057(15) -0.0102(15) O6A 0.045(2) 0.0158(18) 0.0217(18) -0.0037(14) -0.0062(16) -0.0098(16) N1A 0.023(2) 0.022(2) 0.021(2) -0.0049(17) 0.0018(17) -0.0006(17) C1A 0.021(3) 0.023(3) 0.024(3) -0.005(2) -0.005(2) -0.002(2) C2A 0.030(3) 0.018(3) 0.026(3) -0.001(2) -0.004(2) -0.005(2) C3A 0.035(3) 0.014(2) 0.030(3) -0.003(2) -0.012(2) -0.002(2) C4A 0.029(3) 0.017(3) 0.021(3) 0.002(2) -0.007(2) -0.006(2) C5A 0.031(3) 0.015(3) 0.028(3) -0.002(2) -0.006(2) 0.001(2) C6A 0.025(3) 0.021(3) 0.022(3) -0.005(2) 0.001(2) 0.001(2) C7A 0.022(3) 0.014(2) 0.023(3) -0.002(2) -0.006(2) -0.0066(19) C8A 0.029(3) 0.018(3) 0.024(3) -0.003(2) -0.006(2) 0.003(2) C9A 0.031(3) 0.020(3) 0.024(3) -0.003(2) -0.001(2) 0.000(2) C10A 0.021(3) 0.024(3) 0.017(2) -0.004(2) -0.007(2) 0.000(2) C11A 0.023(3) 0.020(2) 0.020(2) -0.0051(19) -0.0031(19) -0.0015(19) C12A 0.027(3) 0.021(3) 0.023(3) -0.001(2) -0.005(2) -0.004(2) C13A 0.031(3) 0.039(3) 0.037(3) 0.013(3) -0.016(3) -0.011(2) C14A 0.032(3) 0.026(3) 0.026(3) 0.007(2) -0.007(2) -0.005(2) S1B 0.0243(6) 0.0151(5) 0.0220(6) -0.0008(5) -0.0057(5) -0.0055(4) O1B 0.041(2) 0.0190(19) 0.041(2) 0.0005(17) 0.0013(18) -0.0047(16) O2B 0.036(2) 0.029(2) 0.028(2) -0.0051(17) 0.0028(17) -0.0096(17) O3B 0.032(2) 0.0147(17) 0.0236(18) -0.0050(14) -0.0001(14) -0.0061(14) O4B 0.024(2) 0.0226(18) 0.0214(19) -0.0038(14) 0.0010(15) -0.0067(14) O5B 0.027(2) 0.027(2) 0.026(2) 0.0032(16) -0.0051(15) -0.0062(15) O6B 0.036(2) 0.0168(17) 0.0282(19) -0.0025(14) -0.0086(16) -0.0090(15) N1B 0.023(2) 0.015(2) 0.025(2) -0.0038(16) -0.0026(17) 0.0001(16) C1B 0.029(3) 0.018(3) 0.022(3) -0.005(2) -0.010(2) -0.001(2) C2B 0.031(3) 0.023(3) 0.025(3) -0.001(2) -0.007(2) -0.004(2) C3B 0.030(3) 0.019(3) 0.026(3) -0.001(2) -0.009(2) -0.004(2) C4B 0.023(3) 0.020(3) 0.023(3) -0.005(2) -0.008(2) -0.003(2) C5B 0.028(3) 0.020(3) 0.024(3) -0.006(2) -0.005(2) 0.001(2) C6B 0.025(3) 0.019(3) 0.020(3) -0.003(2) -0.004(2) -0.003(2) C7B 0.026(3) 0.020(3) 0.020(3) 0.000(2) -0.009(2) -0.001(2) C8B 0.032(3) 0.014(2) 0.023(3) -0.003(2) -0.004(2) -0.006(2) C9B 0.024(3) 0.023(3) 0.019(3) -0.002(2) -0.003(2) -0.005(2) C10B 0.023(3) 0.016(2) 0.021(3) -0.003(2) -0.005(2) -0.0058(19) C11B 0.023(3) 0.019(2) 0.021(2) -0.0037(19) 0.0010(19) -0.0054(19) C12B 0.028(3) 0.024(3) 0.025(3) -0.002(2) -0.006(2) -0.007(2) C13B 0.027(3) 0.033(3) 0.033(3) -0.002(2) -0.012(2) -0.001(2) C14B 0.036(3) 0.025(3) 0.027(3) 0.003(2) -0.006(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1A O6A 1.418(4) . ? S1A O5A 1.428(4) . ? S1A N1A 1.621(5) . ? S1A C7A 1.778(5) . ? O1A C1A 1.305(6) . ? O1A H15A 0.8400 . ? O2A C1A 1.234(7) . ? O3A C10A 1.271(6) . ? O3A H16A 0.8400 . ? O4A C10A 1.247(6) . ? N1A C11A 1.448(7) . ? N1A H17A 0.83(2) . ? C1A C2A 1.469(8) . ? C2A C3A 1.327(8) . ? C2A H2A 0.9500 . ? C3A C4A 1.463(8) . ? C3A H3A 0.9500 . ? C4A C5A 1.391(8) . ? C4A C9A 1.406(7) . ? C5A C6A 1.377(8) . ? C5A H5A 0.9500 . ? C6A C7A 1.397(7) . ? C6A H6A 0.9500 . ? C7A C8A 1.371(8) . ? C8A C9A 1.381(8) . ? C8A H8A 0.9500 . ? C9A H9A 0.9500 . ? C10A C11A 1.531(7) . ? C11A C12A 1.544(7) . ? C11A H11A 1.0000 . ? C12A C14A 1.510(8) . ? C12A C13A 1.532(8) . ? C12A H12A 1.0000 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? C14A H14A 0.9800 . ? C14A H14B 0.9800 . ? C14A H14C 0.9800 . ? S1B O5B 1.414(4) . ? S1B O6B 1.438(4) . ? S1B N1B 1.634(5) . ? S1B C7B 1.775(6) . ? O1B C1B 1.273(7) . ? O1B H15B 0.8400 . ? O2B C1B 1.258(7) . ? O3B C10B 1.336(6) . ? O3B H16B 0.8400 . ? O4B C10B 1.211(6) . ? N1B C11B 1.459(6) . ? N1B H17B 0.84(2) . ? C1B C2B 1.480(8) . ? C2B C3B 1.323(8) . ? C2B H2B 0.9500 . ? C3B C4B 1.482(8) . ? C3B H3B 0.9500 . ? C4B C5B 1.392(8) . ? C4B C9B 1.409(7) . ? C5B C6B 1.382(8) . ? C5B H5B 0.9500 . ? C6B C7B 1.378(7) . ? C6B H6B 0.9500 . ? C7B C8B 1.385(8) . ? C8B C9B 1.376(8) . ? C8B H8B 0.9500 . ? C9B H9B 0.9500 . ? C10B C11B 1.517(7) . ? C11B C12B 1.551(8) . ? C11B H11B 1.0000 . ? C12B C13B 1.518(8) . ? C12B C14B 1.521(8) . ? C12B H12B 1.0000 . ? C13B H13D 0.9800 . ? C13B H13E 0.9800 . ? C13B H13F 0.9800 . ? C14B H14D 0.9800 . ? C14B H14E 0.9800 . ? C14B H14F 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 O6A S1A O5A 121.0(2) . . ? O6A S1A N1A 108.9(2) . . ? O5A S1A N1A 104.8(2) . . ? O6A S1A C7A 106.2(3) . . ? O5A S1A C7A 108.8(2) . . ? N1A S1A C7A 106.4(2) . . ? C1A O1A H15A 109.5 . . ? C10A O3A H16A 109.5 . . ? C11A N1A S1A 122.4(3) . . ? C11A N1A H17A 122(4) . . ? S1A N1A H17A 111(4) . . ? O2A C1A O1A 124.2(5) . . ? O2A C1A C2A 119.8(5) . . ? O1A C1A C2A 116.0(5) . . ? C3A C2A C1A 123.8(5) . . ? C3A C2A H2A 118.1 . . ? C1A C2A H2A 118.1 . . ? C2A C3A C4A 126.7(5) . . ? C2A C3A H3A 116.7 . . ? C4A C3A H3A 116.7 . . ? C5A C4A C9A 118.8(5) . . ? C5A C4A C3A 119.2(5) . . ? C9A C4A C3A 122.0(5) . . ? C6A C5A C4A 121.1(5) . . ? C6A C5A H5A 119.4 . . ? C4A C5A H5A 119.4 . . ? C5A C6A C7A 119.0(5) . . ? C5A C6A H6A 120.5 . . ? C7A C6A H6A 120.5 . . ? C8A C7A C6A 120.8(5) . . ? C8A C7A S1A 120.6(4) . . ? C6A C7A S1A 118.4(4) . . ? C7A C8A C9A 120.1(5) . . ? C7A C8A H8A 119.9 . . ? C9A C8A H8A 119.9 . . ? C8A C9A C4A 120.0(5) . . ? C8A C9A H9A 120.0 . . ? C4A C9A H9A 120.0 . . ? O4A C10A O3A 125.0(5) . . ? O4A C10A C11A 118.4(4) . . ? O3A C10A C11A 116.5(4) . . ? N1A C11A C10A 112.7(4) . . ? N1A C11A C12A 110.1(4) . . ? C10A C11A C12A 108.7(4) . . ? N1A C11A H11A 108.4 . . ? C10A C11A H11A 108.4 . . ? C12A C11A H11A 108.4 . . ? C14A C12A C13A 110.8(5) . . ? C14A C12A C11A 111.5(4) . . ? C13A C12A C11A 110.7(4) . . ? C14A C12A H12A 107.9 . . ? C13A C12A H12A 107.9 . . ? C11A C12A H12A 107.9 . . ? C12A C13A H13A 109.5 . . ? C12A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C12A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C12A C14A H14A 109.5 . . ? C12A C14A H14B 109.5 . . ? H14A C14A H14B 109.5 . . ? C12A C14A H14C 109.5 . . ? H14A C14A H14C 109.5 . . ? H14B C14A H14C 109.5 . . ? O5B S1B O6B 121.5(2) . . ? O5B S1B N1B 107.9(2) . . ? O6B S1B N1B 104.6(2) . . ? O5B S1B C7B 107.5(2) . . ? O6B S1B C7B 108.5(3) . . ? N1B S1B C7B 105.8(2) . . ? C1B O1B H15B 109.5 . . ? C10B O3B H16B 109.5 . . ? C11B N1B S1B 120.8(3) . . ? C11B N1B H17B 116(4) . . ? S1B N1B H17B 117(3) . . ? O2B C1B O1B 123.3(5) . . ? O2B C1B C2B 118.9(5) . . ? O1B C1B C2B 117.8(5) . . ? C3B C2B C1B 122.7(5) . . ? C3B C2B H2B 118.6 . . ? C1B C2B H2B 118.6 . . ? C2B C3B C4B 125.8(5) . . ? C2B C3B H3B 117.1 . . ? C4B C3B H3B 117.1 . . ? C5B C4B C9B 118.9(5) . . ? C5B C4B C3B 119.2(5) . . ? C9B C4B C3B 121.9(5) . . ? C6B C5B C4B 120.7(5) . . ? C6B C5B H5B 119.7 . . ? C4B C5B H5B 119.7 . . ? C7B C6B C5B 119.1(5) . . ? C7B C6B H6B 120.4 . . ? C5B C6B H6B 120.4 . . ? C6B C7B C8B 121.7(5) . . ? C6B C7B S1B 118.9(4) . . ? C8B C7B S1B 119.2(4) . . ? C9B C8B C7B 119.1(5) . . ? C9B C8B H8B 120.5 . . ? C7B C8B H8B 120.5 . . ? C8B C9B C4B 120.4(5) . . ? C8B C9B H9B 119.8 . . ? C4B C9B H9B 119.8 . . ? O4B C10B O3B 123.8(5) . . ? O4B C10B C11B 124.3(5) . . ? O3B C10B C11B 111.9(4) . . ? N1B C11B C10B 111.9(4) . . ? N1B C11B C12B 112.4(4) . . ? C10B C11B C12B 109.1(4) . . ? N1B C11B H11B 107.8 . . ? C10B C11B H11B 107.8 . . ? C12B C11B H11B 107.8 . . ? C13B C12B C14B 110.3(5) . . ? C13B C12B C11B 113.5(4) . . ? C14B C12B C11B 111.3(5) . . ? C13B C12B H12B 107.1 . . ? C14B C12B H12B 107.1 . . ? C11B C12B H12B 107.1 . . ? C12B C13B H13D 109.5 . . ? C12B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C12B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? C12B C14B H14D 109.5 . . ? C12B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C12B C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 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 O6A S1A N1A C11A 54.2(4) . . . . ? O5A S1A N1A C11A -175.1(4) . . . . ? C7A S1A N1A C11A -59.9(4) . . . . ? O2A C1A C2A C3A 176.9(5) . . . . ? O1A C1A C2A C3A -3.0(8) . . . . ? C1A C2A C3A C4A -177.5(5) . . . . ? C2A C3A C4A C5A -178.0(5) . . . . ? C2A C3A C4A C9A 2.6(9) . . . . ? C9A C4A C5A C6A 2.7(8) . . . . ? C3A C4A C5A C6A -176.7(5) . . . . ? C4A C5A C6A C7A 0.6(8) . . . . ? C5A C6A C7A C8A -3.1(8) . . . . ? C5A C6A C7A S1A 172.7(4) . . . . ? O6A S1A C7A C8A -8.8(5) . . . . ? O5A S1A C7A C8A -140.5(4) . . . . ? N1A S1A C7A C8A 107.1(5) . . . . ? O6A S1A C7A C6A 175.4(4) . . . . ? O5A S1A C7A C6A 43.7(5) . . . . ? N1A S1A C7A C6A -68.7(5) . . . . ? C6A C7A C8A C9A 2.1(8) . . . . ? S1A C7A C8A C9A -173.6(4) . . . . ? C7A C8A C9A C4A 1.3(8) . . . . ? C5A C4A C9A C8A -3.7(8) . . . . ? C3A C4A C9A C8A 175.7(5) . . . . ? S1A N1A C11A C10A 75.3(5) . . . . ? S1A N1A C11A C12A -163.1(3) . . . . ? O4A C10A C11A N1A -128.2(5) . . . . ? O3A C10A C11A N1A 54.6(6) . . . . ? O4A C10A C11A C12A 109.4(5) . . . . ? O3A C10A C11A C12A -67.8(5) . . . . ? N1A C11A C12A C14A 59.4(6) . . . . ? C10A C11A C12A C14A -176.6(5) . . . . ? N1A C11A C12A C13A -176.8(4) . . . . ? C10A C11A C12A C13A -52.8(6) . . . . ? O5B S1B N1B C11B 50.6(4) . . . . ? O6B S1B N1B C11B -178.8(4) . . . . ? C7B S1B N1B C11B -64.2(4) . . . . ? O2B C1B C2B C3B -175.9(5) . . . . ? O1B C1B C2B C3B 4.5(8) . . . . ? C1B C2B C3B C4B 176.6(5) . . . . ? C2B C3B C4B C5B 177.7(6) . . . . ? C2B C3B C4B C9B -3.9(9) . . . . ? C9B C4B C5B C6B -1.4(8) . . . . ? C3B C4B C5B C6B 177.0(5) . . . . ? C4B C5B C6B C7B -0.8(8) . . . . ? C5B C6B C7B C8B 2.6(8) . . . . ? C5B C6B C7B S1B -173.1(4) . . . . ? O5B S1B C7B C6B -16.9(5) . . . . ? O6B S1B C7B C6B -149.9(4) . . . . ? N1B S1B C7B C6B 98.2(5) . . . . ? O5B S1B C7B C8B 167.3(4) . . . . ? O6B S1B C7B C8B 34.3(5) . . . . ? N1B S1B C7B C8B -77.5(5) . . . . ? C6B C7B C8B C9B -2.0(8) . . . . ? S1B C7B C8B C9B 173.7(4) . . . . ? C7B C8B C9B C4B -0.3(8) . . . . ? C5B C4B C9B C8B 2.0(8) . . . . ? C3B C4B C9B C8B -176.3(5) . . . . ? S1B N1B C11B C10B 75.9(5) . . . . ? S1B N1B C11B C12B -161.0(4) . . . . ? O4B C10B C11B N1B 36.3(7) . . . . ? O3B C10B C11B N1B -145.6(4) . . . . ? O4B C10B C11B C12B -88.7(6) . . . . ? O3B C10B C11B C12B 89.4(5) . . . . ? N1B C11B C12B C13B -64.2(6) . . . . ? C10B C11B C12B C13B 60.5(6) . . . . ? N1B C11B C12B C14B 60.9(6) . . . . ? C10B C11B C12B C14B -174.4(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 O1B H15B O4A 0.84 1.81 2.643(5) 168.8 . O3A H16A O2B 0.84 1.84 2.678(5) 172.3 . O1A H15A O4B 0.84 1.83 2.665(5) 175.2 . O3B H16B O2A 0.84 1.83 2.660(5) 171.2 . N1B H17B O2A 0.84(2) 2.29(3) 3.042(6) 150(5) 1_565 N1A H17A O3B 0.83(2) 2.31(3) 3.065(5) 152(5) 1_446 C5A H5A O6A 0.95 2.49 3.335(7) 148.6 1_565 C5B H5B O6B 0.95 2.31 3.188(6) 153.3 1_545 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 67.88 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.457 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.076 data_kaw126_twin5_DVal(reacted)_838812 _database_code_depnum_ccdc_archive 'CCDC 838812' #TrackingRef 'web_deposit_cif_file_0_KraigA.Wheeler_1320357917.kaw126_pub.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H34 N2 O12 S2' _chemical_formula_sum 'C28 H34 N2 O12 S2' _chemical_formula_weight 654.71 _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 7.8647(3) _cell_length_b 8.0522(3) _cell_length_c 11.7930(5) _cell_angle_alpha 83.951(2) _cell_angle_beta 77.725(2) _cell_angle_gamma 89.754(2) _cell_volume 725.57(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4671 _cell_measurement_theta_min 5.205 _cell_measurement_theta_max 67.310 _exptl_crystal_description 'transparent plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.344 _exptl_crystal_size_mid 0.286 _exptl_crystal_size_min 0.134 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 2.270 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.458 _exptl_absorpt_correction_T_max 0.738 _exptl_absorpt_process_details 'TWINABS (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 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 4698 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 67.32 _reflns_number_total 4698 _reflns_number_gt 4326 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement APEX2 _computing_data_reduction ; SAINT (Bruker, 2010) and XPREP (Bruker, 2010) ; _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. The data were collected as a two component twin (60:40 ratio) and scaled using Twinabs. The structure was solved using reflections from the strongest component via hklf4 format. The structure was refined using both components in hklf5 format. All nonhydrogen atoms were located in a series of difference Fourier electron denisty maps and refined using anisotropic displacement parameters. The C-C bonds of the cyclobutane ring were constrained to the same distance using the SADI command in shelxl. The thermal parameters of photoproduct component (C2C-C6C,C8C, C9C, C2D-C6D, C8D, C9D) were restrained using the SADI command. The N-H and O-H hydrogen atoms were located in difference density maps and given Uiso = 1.2 x Ueq of the attached N/O atom. The O-H hydrogen atoms were constrained to 0.85(2) angstroms. All other hydrogen atoms were placed in idealized positions with Uiso = 1.2 x Ueq (1.5 x Ueq for methyl groups) of the attached atom. Molecular disorder that relates to the [2+2] photodimerization reaction was modeled using the refinement of occupancy factors. The ratio of 84:16 (reactant:product) provided assessment of the degree of reaction conversion. ; _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^)+(0.0693P)^2^+0.2523P] 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 0.09(2) _refine_ls_number_reflns 4698 _refine_ls_number_parameters 549 _refine_ls_number_restraints 115 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1292 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 1.492 _refine_ls_shift/su_mean 0.003 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 0.30978(11) 0.88479(10) 0.47808(7) 0.0318(2) Uani 1 1 d . A . O1A O 0.7716(3) 1.8052(3) 0.0747(2) 0.0377(7) Uani 1 1 d D A . H3 H 0.824(4) 1.895(3) 0.045(4) 0.045 Uiso 1 1 d D . . O2A O 0.9749(3) 1.6690(3) -0.0428(2) 0.0305(6) Uani 1 1 d . A . O3A O 0.5660(3) 1.2033(3) 0.6022(2) 0.0329(6) Uani 1 1 d . . . O4A O 0.7790(3) 1.0778(3) 0.4853(2) 0.0386(7) Uani 1 1 d D . . H7 H 0.815(5) 1.178(2) 0.469(4) 0.046 Uiso 1 1 d D . . O5A O 0.1253(3) 0.8921(3) 0.5089(2) 0.0400(7) Uani 1 1 d . . . O6A O 0.3949(4) 0.7437(3) 0.4289(2) 0.0402(7) Uani 1 1 d . . . N1A N 0.3735(4) 0.8990(3) 0.6016(2) 0.0286(7) Uani 1 1 d D . . H15 H 0.301(4) 0.955(4) 0.644(3) 0.034 Uiso 1 1 d D . . C1A C 0.8446(5) 1.6714(5) 0.0398(3) 0.0305(8) Uani 1 1 d . . . C2A C 0.7603(5) 1.5107(5) 0.0969(4) 0.0298(10) Uani 0.839(2) 1 d P A 1 H2A H 0.8042 1.4104 0.0669 0.036 Uiso 0.839(2) 1 calc PR A 1 C3A C 0.6260(5) 1.4996(5) 0.1883(4) 0.0258(9) Uani 0.839(2) 1 d P A 1 H3A H 0.5810 1.6018 0.2145 0.031 Uiso 0.839(2) 1 calc PR A 1 C4A C 0.5410(5) 1.3459(5) 0.2523(3) 0.0278(10) Uani 0.839(2) 1 d PD A 1 C5A C 0.6032(5) 1.1879(5) 0.2253(3) 0.0260(10) Uani 0.839(2) 1 d PD A 1 H5A H 0.6973 1.1791 0.1608 0.031 Uiso 0.839(2) 1 calc PR A 1 C6A C 0.5280(5) 1.0456(5) 0.2921(3) 0.0239(9) Uani 0.839(2) 1 d PD A 1 H6A H 0.5668 0.9378 0.2736 0.029 Uiso 0.839(2) 1 calc PR A 1 C7A C 0.3948(5) 1.0647(5) 0.3866(3) 0.0346(11) Uani 1.000(11) 1 d . . . C8A C 0.3231(6) 1.2141(6) 0.4117(4) 0.0326(13) Uani 0.839(2) 1 d PD A 1 H8A H 0.2232 1.2202 0.4725 0.039 Uiso 0.839(2) 1 calc PR A 1 C9A C 0.4015(5) 1.3586(5) 0.3448(4) 0.0268(10) Uani 0.839(2) 1 d PD A 1 H9A H 0.3590 1.4654 0.3629 0.032 Uiso 0.839(2) 1 calc PR A 1 C10A C 0.6372(4) 1.0764(4) 0.5620(3) 0.0274(8) Uani 1 1 d . . . C11A C 0.5545(4) 0.9067(4) 0.6096(3) 0.0269(8) Uani 1 1 d . . . H11A H 0.6193 0.8206 0.5631 0.032 Uiso 1 1 calc R . . C12A C 0.5716(5) 0.8687(5) 0.7372(3) 0.0294(8) Uani 1 1 d . . . H12A H 0.5045 0.9539 0.7835 0.035 Uiso 1 1 calc R . . C13A C 0.7623(5) 0.8836(5) 0.7453(4) 0.0409(10) Uani 1 1 d . . . H13A H 0.7714 0.8641 0.8273 0.061 Uiso 1 1 calc R . . H13B H 0.8075 0.9958 0.7129 0.061 Uiso 1 1 calc R . . H13C H 0.8304 0.8004 0.7010 0.061 Uiso 1 1 calc R . . C14A C 0.4976(5) 0.6982(5) 0.7892(3) 0.0368(9) Uani 1 1 d . . . H14A H 0.3728 0.6944 0.7900 0.055 Uiso 1 1 calc R . . H14B H 0.5152 0.6763 0.8692 0.055 Uiso 1 1 calc R . . H14C H 0.5568 0.6132 0.7422 0.055 Uiso 1 1 calc R . . S1B S 1.32334(10) 2.32074(9) -0.01105(7) 0.0279(2) Uani 1 1 d . A . O1B O 0.9177(4) 1.3701(3) 0.3935(3) 0.0442(8) Uani 1 1 d . A . H19 H 0.663(5) 1.409(3) 0.539(4) 0.053 Uiso 1 1 d D . . O2B O 0.7110(3) 1.5019(3) 0.5107(2) 0.0378(7) Uani 1 1 d D A . O3B O 1.1211(3) 1.9455(3) -0.1666(2) 0.0309(6) Uani 1 1 d D . . H5 H 1.072(4) 1.854(3) -0.136(3) 0.037 Uiso 1 1 d D . . O4B O 0.9437(3) 2.0813(3) -0.0331(2) 0.0322(6) Uani 1 1 d . . . O5B O 1.4898(3) 2.2870(3) -0.0800(2) 0.0336(6) Uani 1 1 d . . . O6B O 1.3022(4) 2.4553(3) 0.0606(2) 0.0374(7) Uani 1 1 d . . . N1B N 1.1874(4) 2.3530(3) -0.0933(2) 0.0276(7) Uani 1 1 d D . . H12 H 1.104(3) 2.415(4) -0.072(3) 0.033 Uiso 1 1 d D . . C1B C 0.8450(5) 1.5004(4) 0.4262(3) 0.0289(8) Uani 1 1 d . . . C2B C 0.9198(5) 1.6656(5) 0.3705(4) 0.0278(10) Uani 0.839(2) 1 d P A 1 H2B H 0.8718 1.7636 0.4019 0.033 Uiso 0.839(2) 1 calc PR A 1 C3B C 1.0524(5) 1.6811(5) 0.2777(3) 0.0246(9) Uani 0.839(2) 1 d P A 1 H3B H 1.1031 1.5814 0.2507 0.030 Uiso 0.839(2) 1 calc PR A 1 C4B C 1.1257(5) 1.8401(5) 0.2144(3) 0.0213(9) Uani 0.839(2) 1 d PD A 1 C5B C 1.0606(6) 1.9962(5) 0.2434(4) 0.0272(10) Uani 0.839(2) 1 d PD A 1 H5B H 0.9702 2.0009 0.3106 0.033 Uiso 0.839(2) 1 calc PR A 1 C6B C 1.1236(6) 2.1421(5) 0.1774(4) 0.0266(11) Uani 0.839(2) 1 d PD A 1 H6B H 1.0768 2.2465 0.1978 0.032 Uiso 0.839(2) 1 calc PR A 1 C7B C 1.2540(5) 2.1342(5) 0.0825(3) 0.0290(9) Uani 1 1 d . . . C8B C 1.3348(5) 1.9853(5) 0.0546(3) 0.0210(9) Uani 0.839(2) 1 d PD A 1 H8B H 1.4329 1.9847 -0.0083 0.025 Uiso 0.839(2) 1 calc PR A 1 C9B C 1.2698(6) 1.8402(5) 0.1197(4) 0.0257(11) Uani 0.839(2) 1 d PD A 1 H9B H 1.3225 1.7374 0.1008 0.031 Uiso 0.839(2) 1 calc PR A 1 C10B C 1.0676(4) 2.0805(5) -0.1164(3) 0.0295(8) Uani 1 1 d . . . C11B C 1.1668(4) 2.2369(4) -0.1759(3) 0.0255(8) Uani 1 1 d . . . H11B H 1.2858 2.2030 -0.2144 0.031 Uiso 1 1 calc R . . C12B C 1.0771(5) 2.3155(4) -0.2729(3) 0.0294(9) Uani 1 1 d . . . H12B H 1.0719 2.2282 -0.3265 0.035 Uiso 1 1 calc R . . C13B C 0.8898(5) 2.3684(5) -0.2271(3) 0.0357(9) Uani 1 1 d . . . H13D H 0.8200 2.2709 -0.1863 0.054 Uiso 1 1 calc R . . H13E H 0.8400 2.4155 -0.2927 0.054 Uiso 1 1 calc R . . H13F H 0.8896 2.4528 -0.1729 0.054 Uiso 1 1 calc R . . C14B C 1.1835(5) 2.4626(5) -0.3454(3) 0.0346(9) Uani 1 1 d . . . H14D H 1.1323 2.4997 -0.4125 0.052 Uiso 1 1 calc R . . H14E H 1.3035 2.4281 -0.3732 0.052 Uiso 1 1 calc R . . H14F H 1.1832 2.5547 -0.2973 0.052 Uiso 1 1 calc R . . C2C C 0.8682(17) 1.570(2) 0.1488(14) 0.026(4) Uani 0.161(2) 1 d PDU A 2 H2C H 0.9112 1.4562 0.1311 0.031 Uiso 0.161(2) 1 calc PR A 2 C3C C 0.704(2) 1.555(3) 0.2482(13) 0.032(4) Uani 0.161(2) 1 d PDU A 2 H3C H 0.6208 1.6420 0.2280 0.038 Uiso 0.161(2) 1 calc PR A 2 C4C C 0.603(2) 1.3887(18) 0.2800(17) 0.024(4) Uani 0.161(2) 1 d PDU A 2 C5C C 0.675(3) 1.2375(17) 0.2476(18) 0.029(4) Uani 0.161(2) 1 d PDU A 2 H5C H 0.7795 1.2381 0.1899 0.034 Uiso 0.161(2) 1 calc PR A 2 C6C C 0.596(3) 1.088(2) 0.2977(18) 0.023(4) Uani 0.161(2) 1 d PDU A 2 H6C H 0.6595 0.9889 0.2814 0.028 Uiso 0.161(2) 1 calc PR A 2 C8C C 0.351(2) 1.245(2) 0.3999(18) 0.008(4) Uani 0.161(2) 1 d PDU A 2 H8C H 0.2376 1.2608 0.4441 0.010 Uiso 0.161(2) 1 calc PR A 2 C9C C 0.447(3) 1.393(3) 0.359(2) 0.041(5) Uani 0.161(2) 1 d PDU A 2 H9C H 0.4044 1.4957 0.3860 0.050 Uiso 0.161(2) 1 calc PR A 2 C2D C 0.8059(19) 1.626(3) 0.3317(16) 0.034(4) Uani 0.161(2) 1 d PDU A 2 H2D H 0.7617 1.7348 0.3593 0.041 Uiso 0.161(2) 1 calc PR A 2 C3D C 0.972(2) 1.643(3) 0.2326(13) 0.025(4) Uani 0.161(2) 1 d PDU A 2 H3D H 1.0595 1.5605 0.2519 0.029 Uiso 0.161(2) 1 calc PR A 2 C4D C 1.059(2) 1.8104(18) 0.1907(17) 0.024(4) Uani 0.161(2) 1 d PDU A 2 C5D C 0.999(2) 1.9622(17) 0.2320(16) 0.016(4) Uani 0.161(2) 1 d PDU A 2 H5D H 0.9073 1.9588 0.2990 0.019 Uiso 0.161(2) 1 calc PR A 2 C6D C 1.067(3) 2.114(2) 0.180(2) 0.021(4) Uani 0.161(2) 1 d PDU A 2 H6D H 1.0053 2.2122 0.2007 0.026 Uiso 0.161(2) 1 calc PR A 2 C8D C 1.276(3) 1.978(2) 0.048(2) 0.043(5) Uani 0.161(2) 1 d PDU A 2 H8D H 1.3387 1.9733 -0.0298 0.052 Uiso 0.161(2) 1 calc PR A 2 C9D C 1.221(3) 1.827(3) 0.110(2) 0.030(5) Uani 0.161(2) 1 d PDU A 2 H9D H 1.2916 1.7317 0.0975 0.036 Uiso 0.161(2) 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(4) 0.0303(4) 0.0264(4) -0.0017(3) -0.0071(3) 0.0027(3) O1A 0.0341(13) 0.0198(12) 0.0521(17) 0.0001(12) 0.0052(12) -0.0040(10) O2A 0.0364(13) 0.0259(12) 0.0248(12) 0.0024(10) 0.0012(10) -0.0028(10) O3A 0.0312(12) 0.0278(12) 0.0327(13) -0.0016(11) 0.0077(10) -0.0012(10) O4A 0.0395(14) 0.0310(13) 0.0339(14) -0.0016(11) 0.0169(11) -0.0054(11) O5A 0.0408(13) 0.0440(15) 0.0346(13) 0.0012(12) -0.0094(11) -0.0012(12) O6A 0.0577(16) 0.0305(13) 0.0325(13) -0.0052(11) -0.0090(12) 0.0036(12) N1A 0.0282(14) 0.0282(15) 0.0248(14) 0.0004(12) 0.0032(11) 0.0018(12) C1A 0.0358(18) 0.0321(18) 0.0212(16) 0.0043(15) -0.0046(14) 0.0065(15) C2A 0.035(2) 0.025(2) 0.027(2) 0.0009(17) -0.0001(17) -0.0082(17) C3A 0.0282(19) 0.0242(19) 0.0238(19) 0.0026(16) -0.0054(16) 0.0024(16) C4A 0.031(2) 0.033(2) 0.0212(19) -0.0012(17) -0.0082(17) -0.0022(18) C5A 0.024(2) 0.028(2) 0.022(2) -0.0007(17) 0.0022(16) -0.0052(17) C6A 0.0261(19) 0.0211(19) 0.0221(19) 0.0003(16) -0.0007(16) -0.0054(17) C7A 0.045(2) 0.032(2) 0.0244(19) -0.0010(16) -0.0042(15) 0.0042(16) C8A 0.033(2) 0.035(3) 0.022(2) 0.006(2) 0.0073(18) -0.003(2) C9A 0.030(2) 0.025(2) 0.022(2) 0.0030(17) -0.0003(17) -0.0024(17) C10A 0.0296(17) 0.0291(18) 0.0191(16) 0.0062(14) 0.0005(13) -0.0006(14) C11A 0.0307(16) 0.0254(16) 0.0224(16) -0.0031(14) -0.0004(13) 0.0014(13) C12A 0.0349(18) 0.0296(18) 0.0219(17) 0.0029(15) -0.0045(14) 0.0015(15) C13A 0.043(2) 0.044(2) 0.035(2) 0.0107(17) -0.0122(16) -0.0071(17) C14A 0.043(2) 0.037(2) 0.0285(19) 0.0069(16) -0.0073(16) -0.0022(17) S1B 0.0380(4) 0.0193(4) 0.0247(4) 0.0025(3) -0.0051(3) -0.0028(3) O1B 0.0455(15) 0.0222(13) 0.0563(18) 0.0057(12) 0.0035(13) -0.0013(11) O2B 0.0462(15) 0.0303(13) 0.0300(13) 0.0019(11) 0.0047(11) -0.0088(12) O3B 0.0403(13) 0.0205(11) 0.0256(12) -0.0029(10) 0.0073(10) -0.0062(10) O4B 0.0340(13) 0.0309(13) 0.0261(12) -0.0048(11) 0.0072(10) -0.0066(10) O5B 0.0286(12) 0.0311(13) 0.0379(14) 0.0051(11) -0.0042(10) -0.0016(10) O6B 0.0566(16) 0.0260(12) 0.0302(13) 0.0007(11) -0.0125(12) 0.0005(12) N1B 0.0327(15) 0.0204(13) 0.0252(14) -0.0004(12) 0.0029(12) -0.0021(12) C1B 0.0364(18) 0.0250(17) 0.0226(16) 0.0004(14) -0.0019(14) -0.0002(15) C2B 0.029(2) 0.023(2) 0.029(2) 0.0013(17) -0.0008(17) -0.0003(17) C3B 0.032(2) 0.0197(19) 0.0205(19) -0.0012(16) -0.0031(16) 0.0048(16) C4B 0.031(2) 0.0157(18) 0.0155(18) 0.0040(15) -0.0034(16) -0.0033(16) C5B 0.031(2) 0.031(2) 0.0176(19) -0.0067(18) 0.0011(16) -0.0045(19) C6B 0.034(2) 0.021(2) 0.021(2) 0.0009(17) 0.0020(18) -0.0012(18) C7B 0.0386(19) 0.0275(18) 0.0194(17) 0.0011(14) -0.0045(14) 0.0024(15) C8B 0.0206(19) 0.0211(19) 0.0181(18) -0.0011(16) 0.0024(15) 0.0009(16) C9B 0.027(2) 0.021(2) 0.027(2) -0.0063(17) -0.0008(17) 0.0063(17) C10B 0.0283(18) 0.0325(19) 0.0248(17) -0.0007(15) -0.0005(14) 0.0026(15) C11B 0.0298(16) 0.0241(16) 0.0194(16) -0.0021(13) 0.0016(13) -0.0047(13) C12B 0.0338(18) 0.0269(18) 0.0248(18) -0.0023(15) -0.0004(15) -0.0077(15) C13B 0.0358(19) 0.040(2) 0.0309(19) -0.0031(17) -0.0066(15) 0.0006(16) C14B 0.0405(19) 0.035(2) 0.0255(18) 0.0061(16) -0.0054(15) -0.0036(16) C2C 0.027(5) 0.022(5) 0.028(5) -0.002(4) -0.002(4) 0.000(4) C3C 0.032(5) 0.032(5) 0.031(5) -0.004(4) -0.006(4) 0.001(4) C4C 0.024(5) 0.024(5) 0.022(5) 0.002(4) -0.004(4) 0.000(4) C5C 0.030(5) 0.027(5) 0.027(5) -0.001(4) -0.004(4) -0.001(4) C6C 0.025(5) 0.025(5) 0.022(5) -0.006(4) -0.007(4) -0.001(4) C8C 0.008(5) 0.010(5) 0.007(5) -0.001(4) -0.002(4) 0.002(4) C9C 0.043(6) 0.040(6) 0.041(6) -0.003(4) -0.009(4) -0.001(4) C2D 0.032(5) 0.032(5) 0.037(5) -0.004(4) -0.003(4) 0.002(4) C3D 0.025(5) 0.026(5) 0.023(5) -0.002(4) -0.006(4) -0.004(4) C4D 0.022(5) 0.024(5) 0.023(5) -0.005(4) -0.002(4) 0.004(4) C5D 0.016(5) 0.017(5) 0.013(5) 0.004(4) -0.002(4) -0.001(4) C6D 0.022(5) 0.022(5) 0.020(5) -0.005(4) -0.003(4) 0.001(4) C8D 0.043(6) 0.046(6) 0.042(6) -0.009(4) -0.009(4) -0.002(4) C9D 0.031(6) 0.031(6) 0.028(6) -0.003(4) -0.007(4) 0.002(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 1.421(3) . ? S1A O6A 1.429(3) . ? S1A N1A 1.653(3) . ? S1A C7A 1.756(4) . ? O1A C1A 1.284(4) . ? O1A H3 0.840(18) . ? O2A C1A 1.257(4) . ? O3A C10A 1.252(4) . ? O4A C10A 1.277(4) . ? O4A H7 0.848(17) . ? N1A C11A 1.448(4) . ? N1A H15 0.837(18) . ? C1A C2A 1.483(5) . ? C1A C2C 1.495(18) . ? C2A C3A 1.335(5) . ? C2A H2A 0.9500 . ? C3A C4A 1.465(6) . ? C3A H3A 0.9500 . ? C4A C9A 1.385(5) . ? C4A C5A 1.404(6) . ? C5A C6A 1.379(5) . ? C5A H5A 0.9500 . ? C6A C7A 1.378(5) . ? C6A H6A 0.9500 . ? C7A C8A 1.360(6) . ? C7A C8C 1.506(17) . ? C7A C6C 1.703(19) . ? C8A C9A 1.401(6) . ? C8A H8A 0.9500 . ? C9A H9A 0.9500 . ? C10A C11A 1.515(5) . ? C11A C12A 1.539(5) . ? C11A H11A 1.0000 . ? C12A C14A 1.509(5) . ? C12A C13A 1.529(5) . ? C12A H12A 1.0000 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? C14A H14A 0.9800 . ? C14A H14B 0.9800 . ? C14A H14C 0.9800 . ? S1B O5B 1.429(3) . ? S1B O6B 1.431(3) . ? S1B N1B 1.593(3) . ? S1B C7B 1.781(4) . ? O1B C1B 1.250(4) . ? O2B C1B 1.288(4) . ? O2B H19 0.844(18) . ? O3B C10B 1.317(4) . ? O3B H5 0.838(17) . ? O4B C10B 1.228(4) . ? N1B C11B 1.452(4) . ? N1B H12 0.835(18) . ? C1B C2B 1.485(5) . ? C1B C2D 1.51(2) . ? C2B C3B 1.338(6) . ? C2B H2B 0.9500 . ? C3B C4B 1.467(5) . ? C3B H3B 0.9500 . ? C4B C5B 1.403(5) . ? C4B C9B 1.412(5) . ? C5B C6B 1.371(6) . ? C5B H5B 0.9500 . ? C6B C7B 1.354(5) . ? C6B H6B 0.9500 . ? C7B C8D 1.36(2) . ? C7B C8B 1.392(5) . ? C7B C6D 1.66(2) . ? C8B C9B 1.365(5) . ? C8B H8B 0.9500 . ? C9B H9B 0.9500 . ? C10B C11B 1.509(5) . ? C11B C12B 1.548(5) . ? C11B H11B 1.0000 . ? C12B C14B 1.525(5) . ? C12B C13B 1.533(5) . ? C12B H12B 1.0000 . ? C13B H13D 0.9800 . ? C13B H13E 0.9800 . ? C13B H13F 0.9800 . ? C14B H14D 0.9800 . ? C14B H14E 0.9800 . ? C14B H14F 0.9800 . ? C2C C3C 1.546(16) . ? C2C C3D 1.567(18) . ? C2C H2C 1.0000 . ? C3C C4C 1.53(2) . ? C3C C2D 1.552(18) . ? C3C H3C 1.0000 . ? C4C C9C 1.382(16) . ? C4C C5C 1.395(16) . ? C5C C6C 1.374(17) . ? C5C H5C 0.9500 . ? C6C H6C 0.9500 . ? C8C C9C 1.395(17) . ? C8C H8C 0.9500 . ? C9C H9C 0.9500 . ? C2D C3D 1.551(17) . ? C2D H2D 1.0000 . ? C3D C4D 1.50(2) . ? C3D H3D 1.0000 . ? C4D C5D 1.405(16) . ? C4D C9D 1.414(17) . ? C5D C6D 1.368(16) . ? C5D H5D 0.9500 . ? C6D H6D 0.9500 . ? C8D C9D 1.374(17) . ? C8D H8D 0.9500 . ? C9D H9D 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 O5A S1A O6A 121.40(17) . . ? O5A S1A N1A 104.49(15) . . ? O6A S1A N1A 106.67(15) . . ? O5A S1A C7A 109.99(17) . . ? O6A S1A C7A 107.79(17) . . ? N1A S1A C7A 105.30(17) . . ? C1A O1A H3 116(3) . . ? C10A O4A H7 107(3) . . ? C11A N1A S1A 123.5(2) . . ? C11A N1A H15 119(2) . . ? S1A N1A H15 109(3) . . ? O2A C1A O1A 124.2(3) . . ? O2A C1A C2A 118.9(3) . . ? O1A C1A C2A 116.7(3) . . ? O2A C1A C2C 112.8(6) . . ? O1A C1A C2C 104.7(7) . . ? C2A C1A C2C 50.3(6) . . ? C3A C2A C1A 123.4(4) . . ? C3A C2A H2A 118.3 . . ? C1A C2A H2A 118.3 . . ? C2A C3A C4A 126.6(4) . . ? C2A C3A H3A 116.7 . . ? C4A C3A H3A 116.7 . . ? C9A C4A C5A 119.9(4) . . ? C9A C4A C3A 118.6(4) . . ? C5A C4A C3A 121.4(4) . . ? C6A C5A C4A 120.2(3) . . ? C6A C5A H5A 119.9 . . ? C4A C5A H5A 119.9 . . ? C7A C6A C5A 117.9(4) . . ? C7A C6A H6A 121.1 . . ? C5A C6A H6A 121.1 . . ? C8A C7A C6A 123.9(4) . . ? C8A C7A C8C 12.0(7) . . ? C6A C7A C8C 112.9(7) . . ? C8A C7A C6C 112.2(6) . . ? C6A C7A C6C 21.4(7) . . ? C8C C7A C6C 100.3(8) . . ? C8A C7A S1A 118.1(3) . . ? C6A C7A S1A 118.0(3) . . ? C8C C7A S1A 129.0(7) . . ? C6C C7A S1A 126.4(6) . . ? C7A C8A C9A 117.8(4) . . ? C7A C8A H8A 121.1 . . ? C9A C8A H8A 121.1 . . ? C4A C9A C8A 120.0(4) . . ? C4A C9A H9A 120.0 . . ? C8A C9A H9A 120.0 . . ? O3A C10A O4A 124.8(3) . . ? O3A C10A C11A 118.6(3) . . ? O4A C10A C11A 116.6(3) . . ? N1A C11A C10A 111.9(3) . . ? N1A C11A C12A 110.4(3) . . ? C10A C11A C12A 108.7(3) . . ? N1A C11A H11A 108.6 . . ? C10A C11A H11A 108.6 . . ? C12A C11A H11A 108.6 . . ? C14A C12A C13A 110.6(3) . . ? C14A C12A C11A 111.7(3) . . ? C13A C12A C11A 110.1(3) . . ? C14A C12A H12A 108.1 . . ? C13A C12A H12A 108.1 . . ? C11A C12A H12A 108.1 . . ? C12A C13A H13A 109.5 . . ? C12A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C12A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C12A C14A H14A 109.5 . . ? C12A C14A H14B 109.5 . . ? H14A C14A H14B 109.5 . . ? C12A C14A H14C 109.5 . . ? H14A C14A H14C 109.5 . . ? H14B C14A H14C 109.5 . . ? O5B S1B O6B 120.78(16) . . ? O5B S1B N1B 109.46(15) . . ? O6B S1B N1B 105.57(16) . . ? O5B S1B C7B 106.27(16) . . ? O6B S1B C7B 107.12(16) . . ? N1B S1B C7B 106.91(16) . . ? C1B O2B H19 117(3) . . ? C10B O3B H5 118(2) . . ? C11B N1B S1B 121.3(2) . . ? C11B N1B H12 117(3) . . ? S1B N1B H12 117(3) . . ? O1B C1B O2B 123.9(3) . . ? O1B C1B C2B 119.5(3) . . ? O2B C1B C2B 116.5(3) . . ? O1B C1B C2D 116.2(8) . . ? O2B C1B C2D 104.6(7) . . ? C2B C1B C2D 45.2(7) . . ? C3B C2B C1B 122.3(4) . . ? C3B C2B H2B 118.9 . . ? C1B C2B H2B 118.9 . . ? C2B C3B C4B 125.1(4) . . ? C2B C3B H3B 117.5 . . ? C4B C3B H3B 117.5 . . ? C5B C4B C9B 117.0(3) . . ? C5B C4B C3B 123.3(3) . . ? C9B C4B C3B 119.7(3) . . ? C6B C5B C4B 121.9(4) . . ? C6B C5B H5B 119.0 . . ? C4B C5B H5B 119.0 . . ? C7B C6B C5B 118.6(4) . . ? C7B C6B H6B 120.7 . . ? C5B C6B H6B 120.7 . . ? C6B C7B C8D 113.3(10) . . ? C6B C7B C8B 122.4(3) . . ? C8D C7B C8B 20.4(12) . . ? C6B C7B C6D 14.7(8) . . ? C8D C7B C6D 102.6(11) . . ? C8B C7B C6D 115.6(6) . . ? C6B C7B S1B 118.9(3) . . ? C8D C7B S1B 123.9(10) . . ? C8B C7B S1B 118.6(3) . . ? C6D C7B S1B 123.8(6) . . ? C9B C8B C7B 118.4(3) . . ? C9B C8B H8B 120.8 . . ? C7B C8B H8B 120.8 . . ? C8B C9B C4B 121.2(4) . . ? C8B C9B H9B 119.4 . . ? C4B C9B H9B 119.4 . . ? O4B C10B O3B 123.7(3) . . ? O4B C10B C11B 123.0(3) . . ? O3B C10B C11B 113.3(3) . . ? N1B C11B C10B 112.0(3) . . ? N1B C11B C12B 112.8(3) . . ? C10B C11B C12B 109.1(3) . . ? N1B C11B H11B 107.5 . . ? C10B C11B H11B 107.5 . . ? C12B C11B H11B 107.5 . . ? C14B C12B C13B 110.1(3) . . ? C14B C12B C11B 111.4(3) . . ? C13B C12B C11B 113.5(3) . . ? C14B C12B H12B 107.2 . . ? C13B C12B H12B 107.2 . . ? C11B C12B H12B 107.2 . . ? C12B C13B H13D 109.5 . . ? C12B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C12B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? C12B C14B H14D 109.5 . . ? C12B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C12B C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? C1A C2C C3C 114.1(12) . . ? C1A C2C C3D 120.5(14) . . ? C3C C2C C3D 89.5(11) . . ? C1A C2C H2C 110.3 . . ? C3C C2C H2C 110.3 . . ? C3D C2C H2C 110.3 . . ? C4C C3C C2C 119.4(15) . . ? C4C C3C C2D 122.1(16) . . ? C2C C3C C2D 90.7(11) . . ? C4C C3C H3C 107.7 . . ? C2C C3C H3C 107.7 . . ? C2D C3C H3C 107.7 . . ? C9C C4C C5C 121.0(15) . . ? C9C C4C C3C 115.2(14) . . ? C5C C4C C3C 123.0(14) . . ? C6C C5C C4C 121.2(15) . . ? C6C C5C H5C 119.4 . . ? C4C C5C H5C 119.4 . . ? C5C C6C C7A 125.1(14) . . ? C5C C6C H6C 117.4 . . ? C7A C6C H6C 117.4 . . ? C9C C8C C7A 132.0(14) . . ? C9C C8C H8C 114.0 . . ? C7A C8C H8C 114.0 . . ? C4C C9C C8C 119.4(17) . . ? C4C C9C H9C 120.3 . . ? C8C C9C H9C 120.3 . . ? C1B C2D C3D 106.7(13) . . ? C1B C2D C3C 114.7(16) . . ? C3D C2D C3C 89.9(11) . . ? C1B C2D H2D 114.3 . . ? C3D C2D H2D 114.3 . . ? C3C C2D H2D 114.3 . . ? C4D C3D C2D 120.5(16) . . ? C4D C3D C2C 116.3(15) . . ? C2D C3D C2C 89.9(11) . . ? C4D C3D H3D 109.5 . . ? C2D C3D H3D 109.5 . . ? C2C C3D H3D 109.5 . . ? C5D C4D C9D 113.3(14) . . ? C5D C4D C3D 124.9(13) . . ? C9D C4D C3D 121.6(14) . . ? C6D C5D C4D 123.1(15) . . ? C6D C5D H5D 118.5 . . ? C4D C5D H5D 118.5 . . ? C5D C6D C7B 122.3(14) . . ? C5D C6D H6D 118.9 . . ? C7B C6D H6D 118.9 . . ? C7B C8D C9D 129(2) . . ? C7B C8D H8D 115.3 . . ? C9D C8D H8D 115.4 . . ? C8D C9D C4D 120.8(18) . . ? C8D C9D H9D 119.6 . . ? C4D C9D H9D 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5A S1A N1A C11A -176.2(3) . . . . ? O6A S1A N1A C11A 54.1(3) . . . . ? C7A S1A N1A C11A -60.3(3) . . . . ? O2A C1A C2A C3A 177.1(4) . . . . ? O1A C1A C2A C3A -6.8(6) . . . . ? C2C C1A C2A C3A 80.4(9) . . . . ? C1A C2A C3A C4A -177.2(4) . . . . ? C2A C3A C4A C9A -179.4(4) . . . . ? C2A C3A C4A C5A 3.7(7) . . . . ? C9A C4A C5A C6A -1.3(7) . . . . ? C3A C4A C5A C6A 175.6(4) . . . . ? C4A C5A C6A C7A -1.6(6) . . . . ? C5A C6A C7A C8A 6.0(7) . . . . ? C5A C6A C7A C8C 0.8(10) . . . . ? C5A C6A C7A C6C -56.1(18) . . . . ? C5A C6A C7A S1A -175.3(3) . . . . ? O5A S1A C7A C8A 40.8(4) . . . . ? O6A S1A C7A C8A 175.1(4) . . . . ? N1A S1A C7A C8A -71.3(4) . . . . ? O5A S1A C7A C6A -137.9(3) . . . . ? O6A S1A C7A C6A -3.6(4) . . . . ? N1A S1A C7A C6A 110.0(3) . . . . ? O5A S1A C7A C8C 46.6(11) . . . . ? O6A S1A C7A C8C -179.0(11) . . . . ? N1A S1A C7A C8C -65.4(11) . . . . ? O5A S1A C7A C6C -161.2(10) . . . . ? O6A S1A C7A C6C -26.9(10) . . . . ? N1A S1A C7A C6C 86.7(10) . . . . ? C6A C7A C8A C9A -7.0(8) . . . . ? C8C C7A C8A C9A 17(5) . . . . ? C6C C7A C8A C9A 13.4(10) . . . . ? S1A C7A C8A C9A 174.4(4) . . . . ? C5A C4A C9A C8A 0.3(7) . . . . ? C3A C4A C9A C8A -176.7(4) . . . . ? C7A C8A C9A C4A 3.7(7) . . . . ? S1A N1A C11A C10A 75.0(3) . . . . ? S1A N1A C11A C12A -163.7(2) . . . . ? O3A C10A C11A N1A 54.3(4) . . . . ? O4A C10A C11A N1A -127.6(3) . . . . ? O3A C10A C11A C12A -67.9(4) . . . . ? O4A C10A C11A C12A 110.1(3) . . . . ? N1A C11A C12A C14A 58.9(4) . . . . ? C10A C11A C12A C14A -177.9(3) . . . . ? N1A C11A C12A C13A -177.9(3) . . . . ? C10A C11A C12A C13A -54.7(4) . . . . ? O5B S1B N1B C11B 50.9(3) . . . . ? O6B S1B N1B C11B -177.7(2) . . . . ? C7B S1B N1B C11B -63.8(3) . . . . ? O1B C1B C2B C3B 7.2(6) . . . . ? O2B C1B C2B C3B -176.0(4) . . . . ? C2D C1B C2B C3B -91.7(11) . . . . ? C1B C2B C3B C4B 176.2(4) . . . . ? C2B C3B C4B C5B -1.5(7) . . . . ? C2B C3B C4B C9B 178.0(5) . . . . ? C9B C4B C5B C6B 5.3(7) . . . . ? C3B C4B C5B C6B -175.2(4) . . . . ? C4B C5B C6B C7B -0.9(7) . . . . ? C5B C6B C7B C8D 15.8(15) . . . . ? C5B C6B C7B C8B -4.9(7) . . . . ? C5B C6B C7B C6D 61(3) . . . . ? C5B C6B C7B S1B 174.4(3) . . . . ? O5B S1B C7B C6B 163.1(3) . . . . ? O6B S1B C7B C6B 32.7(4) . . . . ? N1B S1B C7B C6B -80.1(4) . . . . ? O5B S1B C7B C8D -40.8(15) . . . . ? O6B S1B C7B C8D -171.2(15) . . . . ? N1B S1B C7B C8D 76.0(15) . . . . ? O5B S1B C7B C8B -17.6(4) . . . . ? O6B S1B C7B C8B -148.0(3) . . . . ? N1B S1B C7B C8B 99.2(3) . . . . ? O5B S1B C7B C6D 179.4(10) . . . . ? O6B S1B C7B C6D 49.0(11) . . . . ? N1B S1B C7B C6D -63.8(11) . . . . ? C6B C7B C8B C9B 5.8(7) . . . . ? C8D C7B C8B C9B -63(3) . . . . ? C6D C7B C8B C9B -9.1(11) . . . . ? S1B C7B C8B C9B -173.5(3) . . . . ? C7B C8B C9B C4B -1.0(7) . . . . ? C5B C4B C9B C8B -4.3(7) . . . . ? C3B C4B C9B C8B 176.2(4) . . . . ? S1B N1B C11B C10B 75.1(3) . . . . ? S1B N1B C11B C12B -161.2(2) . . . . ? O4B C10B C11B N1B 37.9(5) . . . . ? O3B C10B C11B N1B -145.6(3) . . . . ? O4B C10B C11B C12B -87.8(4) . . . . ? O3B C10B C11B C12B 88.7(4) . . . . ? N1B C11B C12B C14B 61.4(4) . . . . ? C10B C11B C12B C14B -173.4(3) . . . . ? N1B C11B C12B C13B -63.6(4) . . . . ? C10B C11B C12B C13B 61.6(4) . . . . ? O2A C1A C2C C3C -174.0(10) . . . . ? O1A C1A C2C C3C 48.2(13) . . . . ? C2A C1A C2C C3C -64.5(11) . . . . ? O2A C1A C2C C3D 81.4(13) . . . . ? O1A C1A C2C C3D -56.4(12) . . . . ? C2A C1A C2C C3D -169.2(16) . . . . ? C1A C2C C3C C4C 108.0(19) . . . . ? C3D C2C C3C C4C -128.4(17) . . . . ? C1A C2C C3C C2D -123.9(14) . . . . ? C3D C2C C3C C2D -0.4(16) . . . . ? C2C C3C C4C C9C -172.2(19) . . . . ? C2D C3C C4C C9C 76(3) . . . . ? C2C C3C C4C C5C 18(3) . . . . ? C2D C3C C4C C5C -94(2) . . . . ? C9C C4C C5C C6C -3(4) . . . . ? C3C C4C C5C C6C 166(2) . . . . ? C4C C5C C6C C7A 10(3) . . . . ? C8A C7A C6C C5C -5(2) . . . . ? C6A C7A C6C C5C 122(3) . . . . ? C8C C7A C6C C5C -6(2) . . . . ? S1A C7A C6C C5C -164.4(16) . . . . ? C8A C7A C8C C9C 180(7) . . . . ? C6A C7A C8C C9C -22(3) . . . . ? C6C C7A C8C C9C -4(3) . . . . ? S1A C7A C8C C9C 154(2) . . . . ? C5C C4C C9C C8C -6(4) . . . . ? C3C C4C C9C C8C -176(2) . . . . ? C7A C8C C9C C4C 9(4) . . . . ? O1B C1B C2D C3D -45.3(14) . . . . ? O2B C1B C2D C3D 174.2(10) . . . . ? C2B C1B C2D C3D 61.2(10) . . . . ? O1B C1B C2D C3C 52.5(12) . . . . ? O2B C1B C2D C3C -88.0(12) . . . . ? C2B C1B C2D C3C 159.0(17) . . . . ? C4C C3C C2D C1B 18(2) . . . . ? C2C C3C C2D C1B -108.0(14) . . . . ? C4C C3C C2D C3D 126.3(16) . . . . ? C2C C3C C2D C3D 0.4(17) . . . . ? C1B C2D C3D C4D -123.6(18) . . . . ? C3C C2D C3D C4D 120.6(18) . . . . ? C1B C2D C3D C2C 115.5(14) . . . . ? C3C C2D C3D C2C -0.4(16) . . . . ? C1A C2C C3D C4D -6.1(19) . . . . ? C3C C2C C3D C4D -124.1(15) . . . . ? C1A C2C C3D C2D 118.3(14) . . . . ? C3C C2C C3D C2D 0.4(16) . . . . ? C2D C3D C4D C5D -2(3) . . . . ? C2C C3D C4D C5D 104(2) . . . . ? C2D C3D C4D C9D 173(2) . . . . ? C2C C3D C4D C9D -80(3) . . . . ? C9D C4D C5D C6D 14(3) . . . . ? C3D C4D C5D C6D -170(2) . . . . ? C4D C5D C6D C7B -14(3) . . . . ? C6B C7B C6D C5D -120(4) . . . . ? C8D C7B C6D C5D 18(3) . . . . ? C8B C7B C6D C5D 2(2) . . . . ? S1B C7B C6D C5D 165.1(16) . . . . ? C6B C7B C8D C9D -19(3) . . . . ? C8B C7B C8D C9D 102(5) . . . . ? C6D C7B C8D C9D -30(3) . . . . ? S1B C7B C8D C9D -176(2) . . . . ? C7B C8D C9D C4D 36(4) . . . . ? C5D C4D C9D C8D -22(4) . . . . ? C3D C4D C9D C8D 162(2) . . . . ? 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 O3B H5 O2A 0.838(17) 1.83(2) 2.652(3) 168(4) . O1A H3 O4B 0.840(18) 1.824(19) 2.662(3) 175(4) . O4A H7 O1B 0.848(17) 1.80(2) 2.624(3) 163(4) . O2B H19 O3A 0.844(18) 1.839(18) 2.683(3) 178(4) . N1A H15 O3B 0.837(18) 2.37(3) 3.075(4) 142(3) 1_446 N1B H12 O2A 0.835(18) 2.30(2) 3.080(4) 155(3) 1_565 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 67.32 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.528 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.065