# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_compound_1 _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef 'Compound 1.cif' #============================================================================ _audit_creation_method SHELXL-97 #============================================================================ # SUBMISSION DETAILS _publ_contact_author_name 'Hong-Bin Zhang' _publ_contact_author_address ; Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University Kunming 650091 P. R. China ; _publ_contact_author_email zhanghb@ynu.edu.cn loop_ _publ_author_name 'Hongbin Zhang' 'Yifu Guang' 'Chengxue Pan' 'Jia Wang' 'Rong Huang' 'Qilin Li' #============================================================================ data_111013c _database_code_depnum_ccdc_archive 'CCDC 867573' #TrackingRef 'Compound 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N O4 S' _chemical_formula_sum 'C15 H17 N O4 S' _chemical_formula_weight 307.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.7222(14) _cell_length_b 10.3371(13) _cell_length_c 12.2852(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.752(2) _cell_angle_gamma 90.00 _cell_volume 1471.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1969 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.96 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9350 _exptl_absorpt_correction_T_max 0.9589 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7904 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2563 _reflns_number_gt 1786 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker apex II' _computing_cell_refinement 'Bruker apex II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.7763P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0046(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2563 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.74402(7) 0.10409(7) 0.47981(7) 0.0408(3) Uani 1 1 d . . . N1 N 0.69618(19) 0.1611(2) 0.58678(19) 0.0347(6) Uani 1 1 d . . . O1 O 0.48308(18) 0.49927(19) 0.63608(17) 0.0463(6) Uani 1 1 d . . . O2 O 0.34651(19) 0.3617(2) 0.46848(19) 0.0619(7) Uani 1 1 d . . . H2 H 0.4005 0.4026 0.4502 0.093 Uiso 1 1 calc R . . O3 O 0.64714(19) 0.0943(2) 0.39406(17) 0.0533(6) Uani 1 1 d . . . O4 O 0.8104(2) -0.0088(2) 0.5162(2) 0.0603(7) Uani 1 1 d . . . C1 C 0.5329(2) 0.4056(3) 0.7197(2) 0.0363(7) Uani 1 1 d . . . H1 H 0.5420 0.4330 0.7969 0.044 Uiso 1 1 calc R . . C2 C 0.4147(3) 0.3903(3) 0.6613(2) 0.0431(8) Uani 1 1 d . . . H2A H 0.3528 0.4097 0.7041 0.052 Uiso 1 1 calc R . . C3 C 0.3848(3) 0.2941(3) 0.5678(3) 0.0447(8) Uani 1 1 d . . . H3 H 0.3189 0.2437 0.5846 0.054 Uiso 1 1 calc R . . C4 C 0.4814(2) 0.1973(3) 0.5577(3) 0.0417(8) Uani 1 1 d . . . H4A H 0.4791 0.1289 0.6114 0.050 Uiso 1 1 calc R . . H4B H 0.4676 0.1583 0.4851 0.050 Uiso 1 1 calc R . . C5 C 0.6009(2) 0.2579(3) 0.5754(2) 0.0321(7) Uani 1 1 d . . . H5 H 0.6090 0.3201 0.5168 0.038 Uiso 1 1 calc R . . C6 C 0.6229(2) 0.3223(3) 0.6867(2) 0.0307(7) Uani 1 1 d . . . C7 C 0.7185(3) 0.2812(3) 0.7476(2) 0.0380(7) Uani 1 1 d . . . H7 H 0.7454 0.3111 0.8182 0.046 Uiso 1 1 calc R . . C8 C 0.7781(3) 0.1814(3) 0.6898(2) 0.0411(8) Uani 1 1 d . . . H8A H 0.8521 0.2125 0.6744 0.049 Uiso 1 1 calc R . . H8B H 0.7897 0.1024 0.7327 0.049 Uiso 1 1 calc R . . C9 C 0.8404(2) 0.2183(3) 0.4381(2) 0.0339(7) Uani 1 1 d . . . C10 C 0.7973(3) 0.3190(3) 0.3696(2) 0.0421(8) Uani 1 1 d . . . H10 H 0.7186 0.3253 0.3447 0.050 Uiso 1 1 calc R . . C11 C 0.8727(3) 0.4104(3) 0.3386(3) 0.0475(9) Uani 1 1 d . . . H11 H 0.8438 0.4774 0.2919 0.057 Uiso 1 1 calc R . . C12 C 0.9906(3) 0.4040(3) 0.3757(2) 0.0412(8) Uani 1 1 d . . . C13 C 1.0313(3) 0.3020(3) 0.4442(3) 0.0439(8) Uani 1 1 d . . . H13 H 1.1100 0.2957 0.4696 0.053 Uiso 1 1 calc R . . C14 C 0.9577(3) 0.2096(3) 0.4755(2) 0.0410(8) Uani 1 1 d . . . H14 H 0.9867 0.1419 0.5214 0.049 Uiso 1 1 calc R . . C15 C 1.0713(3) 0.5040(3) 0.3417(3) 0.0565(10) Uani 1 1 d . . . H15A H 1.0901 0.4822 0.2705 0.085 Uiso 1 1 calc R . . H15B H 1.1407 0.5062 0.3945 0.085 Uiso 1 1 calc R . . H15C H 1.0349 0.5873 0.3383 0.085 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 0.0480(6) 0.0315(4) 0.0450(5) -0.0044(4) 0.0144(4) -0.0019(4) N1 0.0323(15) 0.0377(13) 0.0344(14) 0.0019(11) 0.0064(12) 0.0019(11) O1 0.0494(15) 0.0400(12) 0.0490(13) 0.0111(10) 0.0065(11) 0.0045(10) O2 0.0468(15) 0.0799(19) 0.0533(15) 0.0134(13) -0.0112(12) -0.0017(13) O3 0.0568(15) 0.0573(14) 0.0456(13) -0.0177(11) 0.0074(12) -0.0171(12) O4 0.0749(18) 0.0304(12) 0.0808(17) 0.0038(12) 0.0288(14) 0.0109(11) C1 0.039(2) 0.0381(17) 0.0314(16) 0.0066(14) 0.0053(14) 0.0002(14) C2 0.038(2) 0.0472(19) 0.0467(19) 0.0094(16) 0.0131(16) 0.0035(15) C3 0.0290(19) 0.057(2) 0.047(2) 0.0077(17) 0.0009(15) -0.0042(16) C4 0.0356(19) 0.0462(19) 0.0416(19) -0.0036(15) 0.0007(15) -0.0078(15) C5 0.0305(18) 0.0339(16) 0.0317(17) 0.0050(13) 0.0043(14) -0.0018(13) C6 0.0300(18) 0.0325(16) 0.0299(16) 0.0048(13) 0.0051(14) -0.0050(13) C7 0.0360(19) 0.0447(18) 0.0320(17) 0.0008(14) 0.0007(15) -0.0043(15) C8 0.0331(19) 0.0481(19) 0.0411(19) 0.0098(15) 0.0022(15) 0.0038(15) C9 0.0336(19) 0.0359(16) 0.0353(17) -0.0030(14) 0.0144(14) 0.0017(14) C10 0.0321(19) 0.054(2) 0.0418(19) 0.0064(16) 0.0098(15) 0.0040(15) C11 0.049(2) 0.048(2) 0.049(2) 0.0141(16) 0.0170(17) 0.0079(17) C12 0.041(2) 0.0463(19) 0.0406(18) -0.0108(16) 0.0200(16) -0.0019(16) C13 0.0257(18) 0.059(2) 0.048(2) -0.0060(17) 0.0107(15) 0.0034(16) C14 0.038(2) 0.0448(18) 0.0430(19) 0.0015(15) 0.0138(16) 0.0108(15) C15 0.058(2) 0.056(2) 0.061(2) -0.0110(18) 0.029(2) -0.0124(18) _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 O3 1.430(2) . ? S1 O4 1.436(2) . ? S1 N1 1.616(2) . ? S1 C9 1.763(3) . ? N1 C8 1.483(4) . ? N1 C5 1.491(3) . ? O1 C2 1.443(3) . ? O1 C1 1.467(3) . ? O2 C3 1.419(4) . ? O2 H2 0.8200 . ? C1 C6 1.466(4) . ? C1 C2 1.468(4) . ? C1 H1 0.9800 . ? C2 C3 1.519(4) . ? C2 H2A 0.9800 . ? C3 C4 1.530(4) . ? C3 H3 0.9800 . ? C4 C5 1.520(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.507(4) . ? C5 H5 0.9800 . ? C6 C7 1.319(4) . ? C7 C8 1.485(4) . ? C7 H7 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.385(4) . ? C9 C10 1.385(4) . ? C10 C11 1.386(4) . ? C10 H10 0.9300 . ? C11 C12 1.389(4) . ? C11 H11 0.9300 . ? C12 C13 1.388(4) . ? C12 C15 1.503(4) . ? C13 C14 1.380(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 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 O3 S1 O4 120.26(14) . . ? O3 S1 N1 106.84(13) . . ? O4 S1 N1 106.37(13) . . ? O3 S1 C9 107.79(14) . . ? O4 S1 C9 107.08(14) . . ? N1 S1 C9 108.00(13) . . ? C8 N1 C5 111.3(2) . . ? C8 N1 S1 119.07(19) . . ? C5 N1 S1 121.10(19) . . ? C2 O1 C1 60.60(17) . . ? C3 O2 H2 109.5 . . ? C6 C1 O1 114.9(2) . . ? C6 C1 C2 117.9(3) . . ? O1 C1 C2 58.91(17) . . ? C6 C1 H1 117.4 . . ? O1 C1 H1 117.4 . . ? C2 C1 H1 117.4 . . ? O1 C2 C1 60.49(18) . . ? O1 C2 C3 114.9(2) . . ? C1 C2 C3 122.1(3) . . ? O1 C2 H2A 115.8 . . ? C1 C2 H2A 115.8 . . ? C3 C2 H2A 115.8 . . ? O2 C3 C2 109.5(3) . . ? O2 C3 C4 113.2(3) . . ? C2 C3 C4 113.6(3) . . ? O2 C3 H3 106.7 . . ? C2 C3 H3 106.7 . . ? C4 C3 H3 106.7 . . ? C5 C4 C3 113.3(2) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N1 C5 C6 100.9(2) . . ? N1 C5 C4 113.4(2) . . ? C6 C5 C4 109.8(2) . . ? N1 C5 H5 110.8 . . ? C6 C5 H5 110.8 . . ? C4 C5 H5 110.8 . . ? C7 C6 C1 128.2(3) . . ? C7 C6 C5 112.6(3) . . ? C1 C6 C5 118.6(2) . . ? C6 C7 C8 112.0(3) . . ? C6 C7 H7 124.0 . . ? C8 C7 H7 124.0 . . ? N1 C8 C7 102.5(2) . . ? N1 C8 H8A 111.3 . . ? C7 C8 H8A 111.3 . . ? N1 C8 H8B 111.3 . . ? C7 C8 H8B 111.3 . . ? H8A C8 H8B 109.2 . . ? C14 C9 C10 120.1(3) . . ? C14 C9 S1 120.5(2) . . ? C10 C9 S1 119.3(2) . . ? C9 C10 C11 119.4(3) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C11 C12 121.4(3) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 117.9(3) . . ? C13 C12 C15 121.2(3) . . ? C11 C12 C15 120.9(3) . . ? C14 C13 C12 121.5(3) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C9 119.6(3) . . ? C13 C14 H14 120.2 . . ? C9 C14 H14 120.2 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 O3 S1 N1 C8 179.8(2) . . . . ? O4 S1 N1 C8 50.2(2) . . . . ? C9 S1 N1 C8 -64.5(2) . . . . ? O3 S1 N1 C5 -35.1(2) . . . . ? O4 S1 N1 C5 -164.7(2) . . . . ? C9 S1 N1 C5 80.6(2) . . . . ? C2 O1 C1 C6 108.8(3) . . . . ? C1 O1 C2 C3 -114.3(3) . . . . ? C6 C1 C2 O1 -103.7(3) . . . . ? C6 C1 C2 C3 -1.2(4) . . . . ? O1 C1 C2 C3 102.4(3) . . . . ? O1 C2 C3 O2 -45.8(3) . . . . ? C1 C2 C3 O2 -115.3(3) . . . . ? O1 C2 C3 C4 81.9(3) . . . . ? C1 C2 C3 C4 12.3(4) . . . . ? O2 C3 C4 C5 85.1(3) . . . . ? C2 C3 C4 C5 -40.6(4) . . . . ? C8 N1 C5 C6 -8.4(3) . . . . ? S1 N1 C5 C6 -155.95(18) . . . . ? C8 N1 C5 C4 -125.8(3) . . . . ? S1 N1 C5 C4 86.7(3) . . . . ? C3 C4 C5 N1 169.1(2) . . . . ? C3 C4 C5 C6 57.1(3) . . . . ? O1 C1 C6 C7 142.1(3) . . . . ? C2 C1 C6 C7 -151.4(3) . . . . ? O1 C1 C6 C5 -47.3(3) . . . . ? C2 C1 C6 C5 19.2(4) . . . . ? N1 C5 C6 C7 5.4(3) . . . . ? C4 C5 C6 C7 125.4(3) . . . . ? N1 C5 C6 C1 -166.6(2) . . . . ? C4 C5 C6 C1 -46.6(3) . . . . ? C1 C6 C7 C8 170.6(3) . . . . ? C5 C6 C7 C8 -0.4(3) . . . . ? C5 N1 C8 C7 8.3(3) . . . . ? S1 N1 C8 C7 156.58(19) . . . . ? C6 C7 C8 N1 -4.8(3) . . . . ? O3 S1 C9 C14 -151.6(2) . . . . ? O4 S1 C9 C14 -20.9(3) . . . . ? N1 S1 C9 C14 93.3(2) . . . . ? O3 S1 C9 C10 30.0(3) . . . . ? O4 S1 C9 C10 160.7(2) . . . . ? N1 S1 C9 C10 -85.1(3) . . . . ? C14 C9 C10 C11 0.3(4) . . . . ? S1 C9 C10 C11 178.7(2) . . . . ? C9 C10 C11 C12 -0.7(5) . . . . ? C10 C11 C12 C13 0.8(4) . . . . ? C10 C11 C12 C15 -179.8(3) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C15 C12 C13 C14 -179.8(3) . . . . ? C12 C13 C14 C9 -0.1(4) . . . . ? C10 C9 C14 C13 0.1(4) . . . . ? S1 C9 C14 C13 -178.3(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 O2 H2 O1 0.82 2.11 2.913(3) 165.9 3_666 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.239 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.047 #============================================================================ data_111109a _database_code_depnum_ccdc_archive 'CCDC 867574' #TrackingRef 'Compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N O4 S' _chemical_formula_sum 'C15 H17 N O4 S' _chemical_formula_weight 307.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7625(13) _cell_length_b 10.6733(18) _cell_length_c 17.788(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.621(2) _cell_angle_gamma 90.00 _cell_volume 1460.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1008 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 19.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9410 _exptl_absorpt_correction_T_max 0.9721 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8079 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2585 _reflns_number_gt 1533 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker apex II' _computing_cell_refinement 'Bruker apex II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+0.3923P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2585 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 N1 N 0.1776(3) 0.7226(2) 0.24498(14) 0.0482(7) Uani 1 1 d . . . O1 O -0.0345(3) 0.8059(2) 0.32268(14) 0.0784(9) Uani 1 1 d . . . O2 O -0.0976(3) 0.6095(3) 0.24890(13) 0.0693(8) Uani 1 1 d . . . O3 O 0.4889(3) 0.6492(3) 0.06362(13) 0.0705(8) Uani 1 1 d . . . O4 O 0.1906(4) 0.4814(3) 0.00905(15) 0.0995(11) Uani 1 1 d . . . H4 H 0.0911 0.4543 0.0067 0.149 Uiso 1 1 calc R . . S1 S 0.02282(12) 0.68868(9) 0.29569(5) 0.0548(3) Uani 1 1 d . . . C1 C 0.3147(5) 0.8114(3) 0.2781(2) 0.0705(11) Uani 1 1 d . . . H1A H 0.3409 0.8006 0.3326 0.085 Uiso 1 1 calc R . . H1B H 0.2811 0.8976 0.2670 0.085 Uiso 1 1 calc R . . C2 C 0.4646(5) 0.7739(4) 0.2387(2) 0.0763(12) Uani 1 1 d . . . H2 H 0.5698 0.8168 0.2434 0.092 Uiso 1 1 calc R . . C3 C 0.4318(4) 0.6739(4) 0.19681(19) 0.0554(10) Uani 1 1 d . . . C4 C 0.5352(5) 0.6138(4) 0.1428(2) 0.0730(12) Uani 1 1 d . . . H4A H 0.6584 0.5984 0.1603 0.088 Uiso 1 1 calc R . . C5 C 0.4485(5) 0.5274(4) 0.08775(19) 0.0625(10) Uani 1 1 d . . . H5 H 0.5209 0.4596 0.0720 0.075 Uiso 1 1 calc R . . C6 C 0.2612(5) 0.4975(3) 0.0861(2) 0.0640(11) Uani 1 1 d . . . H6 H 0.2520 0.4175 0.1123 0.077 Uiso 1 1 calc R . . C7 C 0.1617(4) 0.5943(3) 0.12417(17) 0.0526(9) Uani 1 1 d . . . H7A H 0.0455 0.5637 0.1280 0.063 Uiso 1 1 calc R . . H7B H 0.1515 0.6705 0.0942 0.063 Uiso 1 1 calc R . . C8 C 0.2548(4) 0.6219(3) 0.20244(16) 0.0441(8) Uani 1 1 d . . . H8 H 0.2654 0.5448 0.2327 0.053 Uiso 1 1 calc R . . C9 C 0.1124(4) 0.5993(3) 0.37454(17) 0.0459(8) Uani 1 1 d . . . C10 C 0.1222(4) 0.4693(3) 0.3686(2) 0.0583(10) Uani 1 1 d . . . H10 H 0.0805 0.4293 0.3233 0.070 Uiso 1 1 calc R . . C11 C 0.1942(5) 0.4008(4) 0.4303(2) 0.0649(10) Uani 1 1 d . . . H11 H 0.2002 0.3141 0.4261 0.078 Uiso 1 1 calc R . . C12 C 0.2579(4) 0.4565(4) 0.4983(2) 0.0566(10) Uani 1 1 d . . . C13 C 0.2468(5) 0.5847(4) 0.50345(19) 0.0621(10) Uani 1 1 d . . . H13 H 0.2889 0.6237 0.5489 0.075 Uiso 1 1 calc R . . C14 C 0.1744(5) 0.6577(3) 0.44250(19) 0.0574(10) Uani 1 1 d . . . H14 H 0.1677 0.7442 0.4472 0.069 Uiso 1 1 calc R . . C15 C 0.3365(5) 0.3798(4) 0.5657(2) 0.0898(14) Uani 1 1 d . . . H15A H 0.4021 0.4336 0.6021 0.135 Uiso 1 1 calc R . . H15B H 0.4119 0.3171 0.5492 0.135 Uiso 1 1 calc R . . H15C H 0.2455 0.3400 0.5886 0.135 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 N1 0.0518(17) 0.0449(17) 0.0477(16) -0.0076(13) 0.0054(13) 0.0031(14) O1 0.095(2) 0.0708(18) 0.0715(17) -0.0028(14) 0.0191(15) 0.0445(15) O2 0.0412(14) 0.105(2) 0.0593(15) -0.0096(15) -0.0023(11) -0.0014(14) O3 0.0671(17) 0.087(2) 0.0592(16) 0.0140(14) 0.0161(13) -0.0154(15) O4 0.075(2) 0.153(3) 0.0735(19) -0.0549(19) 0.0235(15) -0.036(2) S1 0.0511(6) 0.0630(7) 0.0504(5) -0.0036(5) 0.0077(4) 0.0157(5) C1 0.087(3) 0.053(2) 0.068(2) -0.011(2) -0.002(2) -0.018(2) C2 0.062(3) 0.097(3) 0.068(3) -0.006(2) 0.002(2) -0.026(2) C3 0.046(2) 0.071(3) 0.047(2) 0.0019(19) 0.0005(17) -0.0036(19) C4 0.050(2) 0.116(4) 0.053(2) 0.013(2) 0.0042(19) 0.013(2) C5 0.074(3) 0.065(3) 0.052(2) 0.015(2) 0.025(2) 0.019(2) C6 0.082(3) 0.062(3) 0.053(2) -0.0122(19) 0.028(2) -0.017(2) C7 0.047(2) 0.064(2) 0.048(2) -0.0100(17) 0.0120(16) -0.0129(18) C8 0.050(2) 0.0408(19) 0.0419(18) 0.0013(15) 0.0068(15) 0.0025(16) C9 0.0438(19) 0.049(2) 0.046(2) -0.0064(16) 0.0099(15) 0.0042(17) C10 0.060(2) 0.056(2) 0.059(2) -0.0116(19) 0.0112(19) 0.000(2) C11 0.067(3) 0.049(2) 0.081(3) 0.004(2) 0.021(2) 0.006(2) C12 0.049(2) 0.062(3) 0.061(2) 0.013(2) 0.0160(18) 0.0041(19) C13 0.063(2) 0.078(3) 0.045(2) -0.003(2) 0.0043(18) 0.001(2) C14 0.068(2) 0.049(2) 0.057(2) -0.0049(18) 0.0133(19) 0.0049(19) C15 0.078(3) 0.110(4) 0.084(3) 0.039(3) 0.022(2) 0.020(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 N1 C8 1.486(4) . ? N1 C1 1.487(4) . ? N1 S1 1.636(3) . ? O1 S1 1.432(2) . ? O2 S1 1.440(2) . ? O3 C5 1.418(4) . ? O3 C4 1.456(4) . ? O4 C6 1.417(4) . ? O4 H4 0.8200 . ? S1 C9 1.761(3) . ? C1 C2 1.491(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.307(5) . ? C2 H2 0.9300 . ? C3 C4 1.478(5) . ? C3 C8 1.497(4) . ? C4 C5 1.444(5) . ? C4 H4A 0.9800 . ? C5 C6 1.485(5) . ? C5 H5 0.9800 . ? C6 C7 1.504(4) . ? C6 H6 0.9800 . ? C7 C8 1.510(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8 0.9800 . ? C9 C14 1.388(4) . ? C9 C10 1.395(4) . ? C10 C11 1.375(5) . ? C10 H10 0.9300 . ? C11 C12 1.379(5) . ? C11 H11 0.9300 . ? C12 C13 1.374(5) . ? C12 C15 1.512(5) . ? C13 C14 1.391(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 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 C8 N1 C1 110.3(3) . . ? C8 N1 S1 119.7(2) . . ? C1 N1 S1 117.5(2) . . ? C5 O3 C4 60.3(2) . . ? C6 O4 H4 109.5 . . ? O1 S1 O2 120.01(16) . . ? O1 S1 N1 105.95(15) . . ? O2 S1 N1 106.20(13) . . ? O1 S1 C9 108.28(15) . . ? O2 S1 C9 107.42(16) . . ? N1 S1 C9 108.54(14) . . ? N1 C1 C2 101.8(3) . . ? N1 C1 H1A 111.4 . . ? C2 C1 H1A 111.4 . . ? N1 C1 H1B 111.4 . . ? C2 C1 H1B 111.4 . . ? H1A C1 H1B 109.3 . . ? C3 C2 C1 112.4(3) . . ? C3 C2 H2 123.8 . . ? C1 C2 H2 123.8 . . ? C2 C3 C4 130.0(4) . . ? C2 C3 C8 112.1(3) . . ? C4 C3 C8 117.7(3) . . ? C5 C4 O3 58.5(2) . . ? C5 C4 C3 118.3(3) . . ? O3 C4 C3 115.5(3) . . ? C5 C4 H4A 117.2 . . ? O3 C4 H4A 117.2 . . ? C3 C4 H4A 117.2 . . ? O3 C5 C4 61.1(2) . . ? O3 C5 C6 116.5(3) . . ? C4 C5 C6 121.2(3) . . ? O3 C5 H5 115.6 . . ? C4 C5 H5 115.6 . . ? C6 C5 H5 115.6 . . ? O4 C6 C5 107.3(3) . . ? O4 C6 C7 111.3(3) . . ? C5 C6 C7 113.8(3) . . ? O4 C6 H6 108.1 . . ? C5 C6 H6 108.1 . . ? C7 C6 H6 108.1 . . ? C6 C7 C8 109.7(3) . . ? C6 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? C6 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? N1 C8 C3 101.6(3) . . ? N1 C8 C7 115.7(3) . . ? C3 C8 C7 110.0(3) . . ? N1 C8 H8 109.7 . . ? C3 C8 H8 109.7 . . ? C7 C8 H8 109.7 . . ? C14 C9 C10 119.8(3) . . ? C14 C9 S1 120.3(3) . . ? C10 C9 S1 119.9(3) . . ? C11 C10 C9 119.2(3) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 122.1(4) . . ? C10 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C13 C12 C11 118.0(3) . . ? C13 C12 C15 120.6(4) . . ? C11 C12 C15 121.4(4) . . ? C12 C13 C14 121.8(3) . . ? C12 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C9 C14 C13 119.0(3) . . ? C9 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C8 N1 S1 O1 -174.3(2) . . . . ? C1 N1 S1 O1 47.3(3) . . . . ? C8 N1 S1 O2 -45.7(3) . . . . ? C1 N1 S1 O2 175.9(2) . . . . ? C8 N1 S1 C9 69.6(2) . . . . ? C1 N1 S1 C9 -68.8(3) . . . . ? C8 N1 C1 C2 12.1(4) . . . . ? S1 N1 C1 C2 154.2(2) . . . . ? N1 C1 C2 C3 -6.1(4) . . . . ? C1 C2 C3 C4 172.8(3) . . . . ? C1 C2 C3 C8 -2.2(5) . . . . ? C5 O3 C4 C3 -108.9(4) . . . . ? C2 C3 C4 C5 -161.9(4) . . . . ? C8 C3 C4 C5 12.8(5) . . . . ? C2 C3 C4 O3 -95.5(5) . . . . ? C8 C3 C4 O3 79.2(4) . . . . ? C4 O3 C5 C6 112.7(4) . . . . ? C3 C4 C5 O3 104.1(4) . . . . ? O3 C4 C5 C6 -105.2(4) . . . . ? C3 C4 C5 C6 -1.1(5) . . . . ? O3 C5 C6 O4 73.6(4) . . . . ? C4 C5 C6 O4 144.4(4) . . . . ? O3 C5 C6 C7 -50.0(4) . . . . ? C4 C5 C6 C7 20.8(5) . . . . ? O4 C6 C7 C8 -172.2(3) . . . . ? C5 C6 C7 C8 -50.8(4) . . . . ? C1 N1 C8 C3 -13.2(3) . . . . ? S1 N1 C8 C3 -154.3(2) . . . . ? C1 N1 C8 C7 -132.3(3) . . . . ? S1 N1 C8 C7 86.6(3) . . . . ? C2 C3 C8 N1 9.5(4) . . . . ? C4 C3 C8 N1 -166.2(3) . . . . ? C2 C3 C8 C7 132.6(3) . . . . ? C4 C3 C8 C7 -43.1(4) . . . . ? C6 C7 C8 N1 176.0(3) . . . . ? C6 C7 C8 C3 61.6(4) . . . . ? O1 S1 C9 C14 -22.9(3) . . . . ? O2 S1 C9 C14 -153.8(3) . . . . ? N1 S1 C9 C14 91.7(3) . . . . ? O1 S1 C9 C10 157.6(3) . . . . ? O2 S1 C9 C10 26.6(3) . . . . ? N1 S1 C9 C10 -87.8(3) . . . . ? C14 C9 C10 C11 -0.3(5) . . . . ? S1 C9 C10 C11 179.3(3) . . . . ? C9 C10 C11 C12 -0.2(5) . . . . ? C10 C11 C12 C13 0.4(5) . . . . ? C10 C11 C12 C15 179.9(3) . . . . ? C11 C12 C13 C14 -0.2(5) . . . . ? C15 C12 C13 C14 -179.7(3) . . . . ? C10 C9 C14 C13 0.5(5) . . . . ? S1 C9 C14 C13 -179.0(3) . . . . ? C12 C13 C14 C9 -0.3(5) . . . . ? 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 O4 H4 O4 0.82 2.27 2.960(6) 141.6 3_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.254 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.045 #============================================================================ data_mo_zhb_gyf_663_sad _database_code_depnum_ccdc_archive 'CCDC 867575' #TrackingRef 'compound 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H23 N O6 S, C H4 O' _chemical_formula_sum 'C23 H27 N O7 S' _chemical_formula_weight 461.52 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' '-x, -y, -z' _cell_length_a 9.4618(12) _cell_length_b 11.8536(15) _cell_length_c 12.1246(15) _cell_angle_alpha 117.873(2) _cell_angle_beta 91.857(2) _cell_angle_gamma 110.815(2) _cell_volume 1090.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7431 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.38 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9176 _exptl_absorpt_correction_T_max 0.9585 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14264 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.41 _reflns_number_total 5452 _reflns_number_gt 4646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.4879P] 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 5452 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.12555(4) 0.28405(3) 0.48684(3) 0.01686(9) Uani 1 1 d . . . O1 O 0.31707(12) -0.27179(12) -0.21446(11) 0.0253(2) Uani 1 1 d . . . O2 O 0.32268(12) -0.32341(13) -0.05208(12) 0.0285(3) Uani 1 1 d . . . O3 O 1.03068(16) -0.36709(12) 0.03090(12) 0.0300(3) Uani 1 1 d . . . O4 O 1.24921(12) -0.13985(11) 0.21790(10) 0.0209(2) Uani 1 1 d . . . H4 H 1.3260 -0.0904 0.2816 0.031 Uiso 1 1 calc R . . O5 O 1.24671(12) 0.27397(11) 0.55137(10) 0.0224(2) Uani 1 1 d . . . O6 O 1.03468(12) 0.35368(11) 0.55954(10) 0.0218(2) Uani 1 1 d . . . O7 O 0.47931(13) 0.97294(13) 0.59589(12) 0.0302(3) Uani 1 1 d . . . H7 H 0.5050 0.9989 0.5431 0.045 Uiso 1 1 calc R . . N1 N 1.00314(13) 0.12323(12) 0.38271(11) 0.0165(2) Uani 1 1 d . . . C1 C 0.46051(16) -0.18753(15) -0.12803(13) 0.0188(3) Uani 1 1 d . . . C2 C 0.46526(16) -0.21941(15) -0.03181(14) 0.0190(3) Uani 1 1 d . . . C3 C 0.59606(17) -0.15623(15) 0.06357(14) 0.0192(3) Uani 1 1 d . . . H3A H 0.5973 -0.1794 0.1286 0.023 Uiso 1 1 calc R . . C4 C 0.72947(16) -0.05471(14) 0.06095(13) 0.0173(3) Uani 1 1 d . . . C5 C 0.87851(16) 0.02053(14) 0.16227(13) 0.0165(3) Uani 1 1 d . . . H5 H 0.9572 0.0887 0.1445 0.020 Uiso 1 1 calc R . . C6 C 0.86389(16) 0.10199(14) 0.30119(13) 0.0180(3) Uani 1 1 d . . . H6A H 0.8645 0.1933 0.3212 0.022 Uiso 1 1 calc R . . H6B H 0.7666 0.0469 0.3144 0.022 Uiso 1 1 calc R . . C7 C 1.20914(16) 0.36726(14) 0.40146(13) 0.0179(3) Uani 1 1 d . . . C8 C 1.35071(17) 0.36951(15) 0.37139(14) 0.0204(3) Uani 1 1 d . . . H8 H 1.4034 0.3283 0.3982 0.024 Uiso 1 1 calc R . . C9 C 1.41405(17) 0.43241(15) 0.30199(14) 0.0226(3) Uani 1 1 d . . . H9 H 1.5117 0.4358 0.2832 0.027 Uiso 1 1 calc R . . C10 C 1.33703(18) 0.49070(15) 0.25921(14) 0.0230(3) Uani 1 1 d . . . C11 C 1.4086(2) 0.56053(19) 0.18530(17) 0.0329(4) Uani 1 1 d . . . H11A H 1.3341 0.5858 0.1548 0.049 Uiso 1 1 calc R . . H11B H 1.4349 0.4955 0.1116 0.049 Uiso 1 1 calc R . . H11C H 1.5033 0.6456 0.2416 0.049 Uiso 1 1 calc R . . C12 C 1.06729(16) 0.02025(14) 0.30379(13) 0.0165(3) Uani 1 1 d . . . H12 H 1.1710 0.0712 0.2935 0.020 Uiso 1 1 calc R . . C13 C 0.95011(16) -0.06949(14) 0.17588(13) 0.0170(3) Uani 1 1 d . . . C14 C 0.22351(18) -0.34470(18) -0.15896(16) 0.0285(3) Uani 1 1 d . . . H14A H 0.1693 -0.4463 -0.2237 0.034 Uiso 1 1 calc R . . H14B H 0.1440 -0.3087 -0.1292 0.034 Uiso 1 1 calc R . . C15 C 0.58706(17) -0.08875(15) -0.13218(13) 0.0196(3) Uani 1 1 d . . . H15 H 0.5833 -0.0659 -0.1973 0.024 Uiso 1 1 calc R . . C16 C 0.72269(17) -0.02291(14) -0.03544(13) 0.0183(3) Uani 1 1 d . . . H16 H 0.8131 0.0458 -0.0357 0.022 Uiso 1 1 calc R . . C17 C 0.91036(17) -0.20626(15) 0.10053(14) 0.0205(3) Uani 1 1 d . . . H17 H 0.8368 -0.2559 0.0206 0.025 Uiso 1 1 calc R . . C18 C 0.97689(19) -0.28614(15) 0.13630(15) 0.0233(3) Uani 1 1 d . . . H18 H 0.8919 -0.3523 0.1520 0.028 Uiso 1 1 calc R . . C19 C 1.11087(19) -0.19110(16) 0.25703(15) 0.0233(3) Uani 1 1 d . . . H19 H 1.1234 -0.2479 0.2939 0.028 Uiso 1 1 calc R . . C20 C 1.08220(18) -0.06845(15) 0.35876(14) 0.0208(3) Uani 1 1 d . . . H20A H 0.9855 -0.1047 0.3843 0.025 Uiso 1 1 calc R . . H20B H 1.1699 -0.0101 0.4360 0.025 Uiso 1 1 calc R . . C21 C 1.13113(17) 0.42736(15) 0.36193(14) 0.0211(3) Uani 1 1 d . . . H21 H 1.0359 0.4277 0.3841 0.025 Uiso 1 1 calc R . . C22 C 1.19473(18) 0.48655(16) 0.28978(15) 0.0239(3) Uani 1 1 d . . . H22 H 1.1405 0.5250 0.2606 0.029 Uiso 1 1 calc R . . C23 C 0.4265(2) 0.82387(19) 0.53365(18) 0.0327(4) Uani 1 1 d . . . H23A H 0.5094 0.7977 0.4990 0.049 Uiso 1 1 calc R . . H23B H 0.3345 0.7779 0.4634 0.049 Uiso 1 1 calc R . . H23C H 0.3994 0.7939 0.5959 0.049 Uiso 1 1 calc R . . H3 H 1.016(5) -0.435(3) 0.015(4) 0.102(14) 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 0.02003(17) 0.01715(16) 0.01610(16) 0.00906(13) 0.00598(12) 0.00966(13) O1 0.0190(5) 0.0303(6) 0.0289(6) 0.0185(5) 0.0037(4) 0.0083(4) O2 0.0158(5) 0.0377(6) 0.0428(7) 0.0307(6) 0.0076(5) 0.0081(5) O3 0.0434(7) 0.0174(5) 0.0363(6) 0.0137(5) 0.0267(5) 0.0187(5) O4 0.0222(5) 0.0228(5) 0.0211(5) 0.0117(4) 0.0086(4) 0.0119(4) O5 0.0233(5) 0.0252(5) 0.0217(5) 0.0139(4) 0.0030(4) 0.0109(4) O6 0.0264(5) 0.0196(5) 0.0193(5) 0.0077(4) 0.0098(4) 0.0123(4) O7 0.0240(6) 0.0339(6) 0.0348(6) 0.0226(5) 0.0028(5) 0.0076(5) N1 0.0191(5) 0.0162(5) 0.0178(5) 0.0088(4) 0.0070(4) 0.0107(4) C1 0.0194(6) 0.0208(6) 0.0188(6) 0.0097(5) 0.0060(5) 0.0115(5) C2 0.0171(6) 0.0203(6) 0.0249(7) 0.0140(6) 0.0104(5) 0.0098(5) C3 0.0230(7) 0.0217(6) 0.0215(7) 0.0150(6) 0.0095(5) 0.0123(6) C4 0.0215(6) 0.0156(6) 0.0173(6) 0.0085(5) 0.0069(5) 0.0101(5) C5 0.0202(6) 0.0149(6) 0.0175(6) 0.0095(5) 0.0065(5) 0.0087(5) C6 0.0195(6) 0.0175(6) 0.0181(6) 0.0080(5) 0.0049(5) 0.0103(5) C7 0.0210(6) 0.0154(6) 0.0180(6) 0.0088(5) 0.0051(5) 0.0081(5) C8 0.0216(7) 0.0199(6) 0.0217(7) 0.0106(6) 0.0058(5) 0.0109(5) C9 0.0220(7) 0.0215(7) 0.0237(7) 0.0106(6) 0.0090(6) 0.0097(6) C10 0.0266(7) 0.0203(7) 0.0205(7) 0.0112(6) 0.0060(6) 0.0070(6) C11 0.0372(9) 0.0348(9) 0.0312(8) 0.0232(7) 0.0122(7) 0.0106(7) C12 0.0223(6) 0.0169(6) 0.0179(6) 0.0108(5) 0.0102(5) 0.0131(5) C13 0.0208(6) 0.0187(6) 0.0189(6) 0.0126(5) 0.0109(5) 0.0113(5) C14 0.0204(7) 0.0346(8) 0.0275(8) 0.0179(7) 0.0058(6) 0.0058(6) C15 0.0260(7) 0.0202(6) 0.0165(6) 0.0108(5) 0.0079(5) 0.0115(6) C16 0.0224(7) 0.0165(6) 0.0173(6) 0.0092(5) 0.0079(5) 0.0083(5) C17 0.0265(7) 0.0184(6) 0.0212(7) 0.0111(6) 0.0125(6) 0.0123(6) C18 0.0335(8) 0.0187(6) 0.0299(8) 0.0161(6) 0.0208(6) 0.0172(6) C19 0.0336(8) 0.0262(7) 0.0308(8) 0.0224(6) 0.0205(6) 0.0217(6) C20 0.0290(7) 0.0245(7) 0.0227(7) 0.0172(6) 0.0131(6) 0.0178(6) C21 0.0202(7) 0.0210(7) 0.0256(7) 0.0131(6) 0.0056(5) 0.0105(5) C22 0.0242(7) 0.0232(7) 0.0281(7) 0.0166(6) 0.0036(6) 0.0093(6) C23 0.0353(9) 0.0361(9) 0.0364(9) 0.0219(8) 0.0133(7) 0.0199(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O5 1.4379(11) . ? S1 O6 1.4389(10) . ? S1 N1 1.6294(12) . ? S1 C7 1.7672(14) . ? O1 C1 1.3796(17) . ? O1 C14 1.4219(19) . ? O2 C2 1.3833(17) . ? O2 C14 1.4390(19) . ? O3 C18 1.4337(17) . ? O3 H3 0.69(3) . ? O4 C19 1.4325(17) . ? O4 H4 0.8400 . ? O7 C23 1.429(2) . ? O7 H7 0.8400 . ? N1 C6 1.4911(17) . ? N1 C12 1.4988(16) . ? C1 C15 1.367(2) . ? C1 C2 1.388(2) . ? C2 C3 1.367(2) . ? C3 C4 1.4147(19) . ? C3 H3A 0.9500 . ? C4 C16 1.3915(19) . ? C4 C5 1.5042(19) . ? C5 C13 1.5153(18) . ? C5 C6 1.5420(18) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.394(2) . ? C7 C21 1.3972(19) . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 C10 1.395(2) . ? C9 H9 0.9500 . ? C10 C22 1.398(2) . ? C10 C11 1.510(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.5079(19) . ? C12 C20 1.5246(18) . ? C12 H12 1.0000 . ? C13 C17 1.3282(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.402(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.507(2) . ? C17 H17 0.9500 . ? C18 C19 1.530(2) . ? C18 H18 1.0000 . ? C19 C20 1.5277(19) . ? C19 H19 1.0000 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.388(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 119.89(6) . . ? O5 S1 N1 106.29(6) . . ? O6 S1 N1 106.41(6) . . ? O5 S1 C7 108.10(7) . . ? O6 S1 C7 107.56(6) . . ? N1 S1 C7 108.10(6) . . ? C1 O1 C14 105.34(11) . . ? C2 O2 C14 105.24(11) . . ? C18 O3 H3 119(4) . . ? C19 O4 H4 109.5 . . ? C23 O7 H7 109.5 . . ? C6 N1 C12 109.93(10) . . ? C6 N1 S1 117.91(9) . . ? C12 N1 S1 118.26(9) . . ? C15 C1 O1 128.08(13) . . ? C15 C1 C2 121.72(13) . . ? O1 C1 C2 110.16(12) . . ? C3 C2 O2 127.95(13) . . ? C3 C2 C1 122.64(13) . . ? O2 C2 C1 109.39(12) . . ? C2 C3 C4 116.93(13) . . ? C2 C3 H3A 121.5 . . ? C4 C3 H3A 121.5 . . ? C16 C4 C3 119.82(13) . . ? C16 C4 C5 119.53(12) . . ? C3 C4 C5 120.64(12) . . ? C4 C5 C13 117.03(11) . . ? C4 C5 C6 114.63(11) . . ? C13 C5 C6 99.90(10) . . ? C4 C5 H5 108.2 . . ? C13 C5 H5 108.2 . . ? C6 C5 H5 108.2 . . ? N1 C6 C5 104.45(10) . . ? N1 C6 H6A 110.9 . . ? C5 C6 H6A 110.9 . . ? N1 C6 H6B 110.9 . . ? C5 C6 H6B 110.9 . . ? H6A C6 H6B 108.9 . . ? C8 C7 C21 120.46(13) . . ? C8 C7 S1 119.73(11) . . ? C21 C7 S1 119.79(11) . . ? C9 C8 C7 119.42(13) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 121.24(14) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C9 C10 C22 118.38(13) . . ? C9 C10 C11 120.57(14) . . ? C22 C10 C11 121.02(14) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 C13 102.61(10) . . ? N1 C12 C20 113.76(11) . . ? C13 C12 C20 111.22(11) . . ? N1 C12 H12 109.7 . . ? C13 C12 H12 109.7 . . ? C20 C12 H12 109.7 . . ? C17 C13 C12 123.18(13) . . ? C17 C13 C5 128.89(14) . . ? C12 C13 C5 107.52(11) . . ? O1 C14 O2 108.57(12) . . ? O1 C14 H14A 110.0 . . ? O2 C14 H14A 110.0 . . ? O1 C14 H14B 110.0 . . ? O2 C14 H14B 110.0 . . ? H14A C14 H14B 108.4 . . ? C1 C15 C16 116.59(13) . . ? C1 C15 H15 121.7 . . ? C16 C15 H15 121.7 . . ? C4 C16 C15 122.29(13) . . ? C4 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C13 C17 C18 122.88(14) . . ? C13 C17 H17 118.6 . . ? C18 C17 H17 118.6 . . ? O3 C18 C17 109.14(12) . . ? O3 C18 C19 109.15(13) . . ? C17 C18 C19 113.31(12) . . ? O3 C18 H18 108.4 . . ? C17 C18 H18 108.4 . . ? C19 C18 H18 108.4 . . ? O4 C19 C20 110.29(12) . . ? O4 C19 C18 107.06(11) . . ? C20 C19 C18 111.87(12) . . ? O4 C19 H19 109.2 . . ? C20 C19 H19 109.2 . . ? C18 C19 H19 109.2 . . ? C12 C20 C19 109.19(11) . . ? C12 C20 H20A 109.8 . . ? C19 C20 H20A 109.8 . . ? C12 C20 H20B 109.8 . . ? C19 C20 H20B 109.8 . . ? H20A C20 H20B 108.3 . . ? C22 C21 C7 119.11(13) . . ? C22 C21 H21 120.4 . . ? C7 C21 H21 120.4 . . ? C21 C22 C10 121.35(14) . . ? C21 C22 H22 119.3 . . ? C10 C22 H22 119.3 . . ? O7 C23 H23A 109.5 . . ? O7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C6 179.95(9) . . . . ? O6 S1 N1 C6 51.09(11) . . . . ? C7 S1 N1 C6 -64.20(11) . . . . ? O5 S1 N1 C12 -43.77(11) . . . . ? O6 S1 N1 C12 -172.62(9) . . . . ? C7 S1 N1 C12 72.09(11) . . . . ? C14 O1 C1 C15 -174.30(15) . . . . ? C14 O1 C1 C2 8.03(16) . . . . ? C14 O2 C2 C3 175.99(15) . . . . ? C14 O2 C2 C1 -5.67(16) . . . . ? C15 C1 C2 C3 -0.9(2) . . . . ? O1 C1 C2 C3 176.97(13) . . . . ? C15 C1 C2 O2 -179.31(13) . . . . ? O1 C1 C2 O2 -1.47(16) . . . . ? O2 C2 C3 C4 178.24(13) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C2 C3 C4 C16 0.4(2) . . . . ? C2 C3 C4 C5 179.81(12) . . . . ? C16 C4 C5 C13 -122.06(13) . . . . ? C3 C4 C5 C13 58.57(17) . . . . ? C16 C4 C5 C6 121.44(13) . . . . ? C3 C4 C5 C6 -57.93(16) . . . . ? C12 N1 C6 C5 -19.46(13) . . . . ? S1 N1 C6 C5 120.18(10) . . . . ? C4 C5 C6 N1 160.88(11) . . . . ? C13 C5 C6 N1 34.89(12) . . . . ? O5 S1 C7 C8 20.33(13) . . . . ? O6 S1 C7 C8 151.13(11) . . . . ? N1 S1 C7 C8 -94.34(12) . . . . ? O5 S1 C7 C21 -161.19(11) . . . . ? O6 S1 C7 C21 -30.39(13) . . . . ? N1 S1 C7 C21 84.14(12) . . . . ? C21 C7 C8 C9 0.2(2) . . . . ? S1 C7 C8 C9 178.65(11) . . . . ? C7 C8 C9 C10 -1.5(2) . . . . ? C8 C9 C10 C22 1.1(2) . . . . ? C8 C9 C10 C11 179.17(14) . . . . ? C6 N1 C12 C13 -4.74(13) . . . . ? S1 N1 C12 C13 -144.23(9) . . . . ? C6 N1 C12 C20 -124.99(13) . . . . ? S1 N1 C12 C20 95.52(13) . . . . ? N1 C12 C13 C17 -145.10(13) . . . . ? C20 C12 C13 C17 -23.11(18) . . . . ? N1 C12 C13 C5 28.14(13) . . . . ? C20 C12 C13 C5 150.12(11) . . . . ? C4 C5 C13 C17 8.9(2) . . . . ? C6 C5 C13 C17 133.27(15) . . . . ? C4 C5 C13 C12 -163.79(11) . . . . ? C6 C5 C13 C12 -39.45(13) . . . . ? C1 O1 C14 O2 -11.50(16) . . . . ? C2 O2 C14 O1 10.66(17) . . . . ? O1 C1 C15 C16 -176.41(13) . . . . ? C2 C1 C15 C16 1.0(2) . . . . ? C3 C4 C16 C15 -0.3(2) . . . . ? C5 C4 C16 C15 -179.65(12) . . . . ? C1 C15 C16 C4 -0.5(2) . . . . ? C12 C13 C17 C18 0.9(2) . . . . ? C5 C13 C17 C18 -170.79(13) . . . . ? C13 C17 C18 O3 -130.38(15) . . . . ? C13 C17 C18 C19 -8.53(19) . . . . ? O3 C18 C19 O4 39.28(14) . . . . ? C17 C18 C19 O4 -82.57(14) . . . . ? O3 C18 C19 C20 160.21(11) . . . . ? C17 C18 C19 C20 38.36(16) . . . . ? N1 C12 C20 C19 166.70(12) . . . . ? C13 C12 C20 C19 51.43(15) . . . . ? O4 C19 C20 C12 58.55(16) . . . . ? C18 C19 C20 C12 -60.49(15) . . . . ? C8 C7 C21 C22 1.4(2) . . . . ? S1 C7 C21 C22 -177.02(11) . . . . ? C7 C21 C22 C10 -1.9(2) . . . . ? C9 C10 C22 C21 0.6(2) . . . . ? C11 C10 C22 C21 -177.48(14) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.436 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.067 #============================================================================ data_a _database_code_depnum_ccdc_archive 'CCDC 867576' #TrackingRef 'compound 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H23 N O6 S' _chemical_formula_sum 'C22 H23 N O6 S' _chemical_formula_weight 429.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.273(2) _cell_length_b 14.335(2) _cell_length_c 9.1567(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.0282(21) _cell_angle_gamma 90.00 _cell_volume 2004.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8398 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 30.08 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9056 _exptl_absorpt_correction_T_max 0.9703 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20929 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 30.12 _reflns_number_total 5699 _reflns_number_gt 4699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.7735P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5699 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.40932(2) 0.35622(2) 0.16271(3) 0.02015(8) Uani 1 1 d . . . O1 O 0.11528(6) 0.65550(6) -0.56028(10) 0.02125(19) Uani 1 1 d . . . O2 O 0.11535(7) 0.49464(6) -0.53802(10) 0.0249(2) Uani 1 1 d . . . O3 O 0.05357(6) 0.21249(6) 0.23224(9) 0.01942(18) Uani 1 1 d . . . H3 H 0.0395 0.2062 0.3204 0.029 Uiso 1 1 calc R . . O4 O -0.00231(6) 0.31068(7) 0.00741(9) 0.01939(18) Uani 1 1 d . . . H4 H -0.0264 0.2643 0.0464 0.029 Uiso 1 1 calc R . . O5 O 0.48396(6) 0.36495(8) 0.06895(11) 0.0269(2) Uani 1 1 d . . . O6 O 0.39561(6) 0.27250(7) 0.24550(11) 0.0258(2) Uani 1 1 d . . . N1 N 0.32253(7) 0.36864(8) 0.05912(11) 0.0184(2) Uani 1 1 d . . . C1 C 0.40146(10) 0.68624(11) 0.57564(17) 0.0310(3) Uani 1 1 d . . . H1A H 0.3548 0.7290 0.5452 0.047 Uiso 1 1 calc R . . H1B H 0.4579 0.7186 0.5720 0.047 Uiso 1 1 calc R . . H1C H 0.3903 0.6649 0.6756 0.047 Uiso 1 1 calc R . . C2 C 0.40356(8) 0.60346(10) 0.47434(15) 0.0243(3) Uani 1 1 d . . . C3 C 0.43134(9) 0.61415(10) 0.32965(15) 0.0256(3) Uani 1 1 d . . . H3A H 0.4484 0.6741 0.2956 0.031 Uiso 1 1 calc R . . C4 C 0.43436(9) 0.53890(10) 0.23562(14) 0.0235(3) Uani 1 1 d . . . H4A H 0.4532 0.5471 0.1376 0.028 Uiso 1 1 calc R . . C5 C 0.40967(8) 0.45071(9) 0.28533(14) 0.0201(2) Uani 1 1 d . . . C6 C 0.32374(8) 0.43529(9) -0.06499(13) 0.0199(2) Uani 1 1 d . . . H6A H 0.3165 0.4020 -0.1589 0.024 Uiso 1 1 calc R . . H6B H 0.3796 0.4703 -0.0673 0.024 Uiso 1 1 calc R . . C7 C 0.24581(8) 0.50198(8) -0.03733(13) 0.0162(2) Uani 1 1 d . . . H7 H 0.2658 0.5526 0.0300 0.019 Uiso 1 1 calc R . . C8 C 0.20865(8) 0.54685(8) -0.17325(13) 0.0158(2) Uani 1 1 d . . . C9 C 0.20705(8) 0.64328(8) -0.18727(13) 0.0176(2) Uani 1 1 d . . . H9 H 0.2281 0.6805 -0.1090 0.021 Uiso 1 1 calc R . . C10 C 0.17520(8) 0.68778(8) -0.31367(13) 0.0186(2) Uani 1 1 d . . . H10 H 0.1736 0.7538 -0.3221 0.022 Uiso 1 1 calc R . . C11 C 0.14663(8) 0.63066(8) -0.42381(13) 0.0168(2) Uani 1 1 d . . . C12 C 0.08472(12) 0.57033(10) -0.62483(16) 0.0324(3) Uani 1 1 d . . . H12A H 0.0199 0.5700 -0.6284 0.039 Uiso 1 1 calc R . . H12B H 0.1072 0.5645 -0.7258 0.039 Uiso 1 1 calc R . . C13 C 0.14679(8) 0.53434(8) -0.41080(13) 0.0171(2) Uani 1 1 d . . . C14 C 0.17597(8) 0.48990(8) -0.28707(13) 0.0173(2) Uani 1 1 d . . . H14 H 0.1743 0.4239 -0.2783 0.021 Uiso 1 1 calc R . . C15 C 0.18406(8) 0.43917(8) 0.04571(12) 0.0153(2) Uani 1 1 d . . . C16 C 0.09753(8) 0.43433(8) 0.03643(13) 0.0165(2) Uani 1 1 d . . . H16 H 0.0680 0.4781 -0.0239 0.020 Uiso 1 1 calc R . . C17 C 0.04409(8) 0.36302(8) 0.11667(13) 0.0160(2) Uani 1 1 d . . . H17 H 0.0006 0.3961 0.1797 0.019 Uiso 1 1 calc R . . C18 C 0.09988(8) 0.29778(8) 0.21378(13) 0.0166(2) Uani 1 1 d . . . H18 H 0.1076 0.3277 0.3116 0.020 Uiso 1 1 calc R . . C19 C 0.18989(8) 0.27878(8) 0.14881(13) 0.0180(2) Uani 1 1 d . . . H19A H 0.2232 0.2358 0.2126 0.022 Uiso 1 1 calc R . . H19B H 0.1839 0.2496 0.0513 0.022 Uiso 1 1 calc R . . C20 C 0.23735(8) 0.37180(8) 0.13616(13) 0.0162(2) Uani 1 1 d . . . H20 H 0.2461 0.3985 0.2360 0.019 Uiso 1 1 calc R . . C21 C 0.38223(8) 0.43805(10) 0.42919(14) 0.0233(3) Uani 1 1 d . . . H21 H 0.3655 0.3781 0.4633 0.028 Uiso 1 1 calc R . . C22 C 0.37986(9) 0.51501(11) 0.52192(15) 0.0250(3) Uani 1 1 d . . . H22 H 0.3616 0.5068 0.6202 0.030 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 0.01429(14) 0.02709(16) 0.01906(15) 0.00615(11) -0.00088(10) 0.00343(11) O1 0.0296(5) 0.0188(4) 0.0153(4) 0.0020(3) -0.0043(3) 0.0015(4) O2 0.0386(6) 0.0181(4) 0.0181(4) -0.0021(3) -0.0102(4) 0.0028(4) O3 0.0252(5) 0.0187(4) 0.0144(4) 0.0016(3) 0.0010(3) -0.0054(3) O4 0.0196(4) 0.0242(4) 0.0143(4) 0.0014(3) -0.0014(3) -0.0043(3) O5 0.0162(4) 0.0392(6) 0.0252(5) 0.0066(4) 0.0031(4) 0.0058(4) O6 0.0221(5) 0.0280(5) 0.0272(5) 0.0103(4) -0.0027(4) 0.0042(4) N1 0.0142(5) 0.0248(5) 0.0162(5) 0.0047(4) -0.0004(4) 0.0027(4) C1 0.0222(7) 0.0388(8) 0.0321(8) -0.0035(6) -0.0011(5) -0.0013(6) C2 0.0131(5) 0.0348(7) 0.0250(6) 0.0004(5) -0.0028(5) -0.0017(5) C3 0.0208(6) 0.0303(7) 0.0257(7) 0.0065(5) -0.0030(5) -0.0054(5) C4 0.0188(6) 0.0332(7) 0.0186(6) 0.0079(5) -0.0013(5) -0.0040(5) C5 0.0127(5) 0.0290(6) 0.0186(6) 0.0057(5) -0.0025(4) -0.0014(5) C6 0.0167(6) 0.0273(6) 0.0159(5) 0.0058(5) 0.0009(4) 0.0030(5) C7 0.0153(5) 0.0193(5) 0.0140(5) 0.0019(4) -0.0004(4) -0.0004(4) C8 0.0143(5) 0.0182(5) 0.0149(5) 0.0020(4) 0.0010(4) 0.0000(4) C9 0.0187(6) 0.0178(5) 0.0161(5) -0.0004(4) -0.0002(4) -0.0019(4) C10 0.0218(6) 0.0151(5) 0.0190(6) 0.0012(4) 0.0005(4) -0.0002(4) C11 0.0171(5) 0.0184(5) 0.0148(5) 0.0029(4) 0.0007(4) 0.0018(4) C12 0.0549(10) 0.0205(6) 0.0219(6) 0.0010(5) -0.0144(6) 0.0011(6) C13 0.0182(5) 0.0179(5) 0.0152(5) -0.0022(4) -0.0009(4) 0.0013(4) C14 0.0188(6) 0.0148(5) 0.0182(5) 0.0007(4) -0.0008(4) 0.0009(4) C15 0.0181(5) 0.0154(5) 0.0126(5) 0.0007(4) 0.0008(4) 0.0010(4) C16 0.0174(5) 0.0171(5) 0.0149(5) 0.0018(4) 0.0015(4) 0.0029(4) C17 0.0160(5) 0.0184(5) 0.0136(5) -0.0008(4) 0.0010(4) 0.0004(4) C18 0.0198(6) 0.0171(5) 0.0129(5) 0.0009(4) -0.0001(4) -0.0025(4) C19 0.0178(6) 0.0183(5) 0.0179(5) 0.0023(4) -0.0012(4) 0.0013(4) C20 0.0142(5) 0.0201(5) 0.0143(5) 0.0022(4) -0.0004(4) 0.0005(4) C21 0.0172(6) 0.0327(7) 0.0200(6) 0.0072(5) -0.0005(5) -0.0047(5) C22 0.0162(6) 0.0394(8) 0.0194(6) 0.0025(5) 0.0005(5) -0.0049(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O5 1.4326(10) . ? S1 O6 1.4348(10) . ? S1 N1 1.6397(11) . ? S1 C5 1.7594(14) . ? O1 C11 1.3847(14) . ? O1 C12 1.4346(16) . ? O2 C13 1.3826(14) . ? O2 C12 1.4240(16) . ? O3 C18 1.4226(14) . ? O3 H3 0.8400 . ? O4 C17 1.4375(14) . ? O4 H4 0.8400 . ? N1 C20 1.4806(15) . ? N1 C6 1.4849(15) . ? C1 C2 1.507(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C22 1.389(2) . ? C2 C3 1.3996(19) . ? C3 C4 1.381(2) . ? C3 H3A 0.9500 . ? C4 C5 1.3956(18) . ? C4 H4A 0.9500 . ? C5 C21 1.3942(18) . ? C6 C7 1.5475(17) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C15 1.5094(16) . ? C7 C8 1.5116(16) . ? C7 H7 1.0000 . ? C8 C9 1.3885(17) . ? C8 C14 1.4149(16) . ? C9 C10 1.4082(17) . ? C9 H9 0.9500 . ? C10 C11 1.3705(17) . ? C10 H10 0.9500 . ? C11 C13 1.3859(17) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.3741(16) . ? C14 H14 0.9500 . ? C15 C16 1.3262(17) . ? C15 C20 1.5104(16) . ? C16 C17 1.5003(16) . ? C16 H16 0.9500 . ? C17 C18 1.5464(16) . ? C17 H17 1.0000 . ? C18 C19 1.5226(17) . ? C18 H18 1.0000 . ? C19 C20 1.5221(17) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20 1.0000 . ? C21 C22 1.393(2) . ? C21 H21 0.9500 . ? C22 H22 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 120.39(6) . . ? O5 S1 N1 106.68(6) . . ? O6 S1 N1 106.17(6) . . ? O5 S1 C5 108.22(6) . . ? O6 S1 C5 107.90(6) . . ? N1 S1 C5 106.74(6) . . ? C11 O1 C12 105.39(9) . . ? C13 O2 C12 105.71(10) . . ? C18 O3 H3 109.5 . . ? C17 O4 H4 109.5 . . ? C20 N1 C6 110.85(9) . . ? C20 N1 S1 115.98(8) . . ? C6 N1 S1 120.17(8) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C22 C2 C3 118.43(13) . . ? C22 C2 C1 121.37(13) . . ? C3 C2 C1 120.19(13) . . ? C4 C3 C2 120.98(13) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 119.69(12) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C21 C5 C4 120.48(13) . . ? C21 C5 S1 120.12(10) . . ? C4 C5 S1 119.35(10) . . ? N1 C6 C7 105.23(9) . . ? N1 C6 H6A 110.7 . . ? C7 C6 H6A 110.7 . . ? N1 C6 H6B 110.7 . . ? C7 C6 H6B 110.7 . . ? H6A C6 H6B 108.8 . . ? C15 C7 C8 115.73(10) . . ? C15 C7 C6 101.22(9) . . ? C8 C7 C6 114.64(10) . . ? C15 C7 H7 108.3 . . ? C8 C7 H7 108.3 . . ? C6 C7 H7 108.3 . . ? C9 C8 C14 120.02(11) . . ? C9 C8 C7 120.43(11) . . ? C14 C8 C7 119.56(10) . . ? C8 C9 C10 122.21(11) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 116.37(11) . . ? C11 C10 H10 121.8 . . ? C9 C10 H10 121.8 . . ? C10 C11 O1 128.35(11) . . ? C10 C11 C13 122.10(11) . . ? O1 C11 C13 109.54(10) . . ? O2 C12 O1 108.16(10) . . ? O2 C12 H12A 110.1 . . ? O1 C12 H12A 110.1 . . ? O2 C12 H12B 110.1 . . ? O1 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? C14 C13 O2 128.06(11) . . ? C14 C13 C11 122.24(11) . . ? O2 C13 C11 109.69(10) . . ? C13 C14 C8 117.01(11) . . ? C13 C14 H14 121.5 . . ? C8 C14 H14 121.5 . . ? C16 C15 C7 128.43(11) . . ? C16 C15 C20 122.60(11) . . ? C7 C15 C20 108.72(10) . . ? C15 C16 C17 123.12(11) . . ? C15 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? O4 C17 C16 106.44(9) . . ? O4 C17 C18 110.87(9) . . ? C16 C17 C18 113.21(10) . . ? O4 C17 H17 108.7 . . ? C16 C17 H17 108.7 . . ? C18 C17 H17 108.7 . . ? O3 C18 C19 109.97(10) . . ? O3 C18 C17 108.31(9) . . ? C19 C18 C17 112.39(10) . . ? O3 C18 H18 108.7 . . ? C19 C18 H18 108.7 . . ? C17 C18 H18 108.7 . . ? C20 C19 C18 107.64(10) . . ? C20 C19 H19A 110.2 . . ? C18 C19 H19A 110.2 . . ? C20 C19 H19B 110.2 . . ? C18 C19 H19B 110.2 . . ? H19A C19 H19B 108.5 . . ? N1 C20 C15 103.40(9) . . ? N1 C20 C19 115.33(10) . . ? C15 C20 C19 110.20(10) . . ? N1 C20 H20 109.2 . . ? C15 C20 H20 109.2 . . ? C19 C20 H20 109.2 . . ? C22 C21 C5 118.73(12) . . ? C22 C21 H21 120.6 . . ? C5 C21 H21 120.6 . . ? C2 C22 C21 121.69(12) . . ? C2 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? 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 C20 -173.94(9) . . . . ? O6 S1 N1 C20 56.52(10) . . . . ? C5 S1 N1 C20 -58.40(10) . . . . ? O5 S1 N1 C6 -36.10(11) . . . . ? O6 S1 N1 C6 -165.65(9) . . . . ? C5 S1 N1 C6 79.43(10) . . . . ? C22 C2 C3 C4 0.7(2) . . . . ? C1 C2 C3 C4 179.46(13) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C21 -0.16(19) . . . . ? C3 C4 C5 S1 177.33(10) . . . . ? O5 S1 C5 C21 -143.44(10) . . . . ? O6 S1 C5 C21 -11.69(12) . . . . ? N1 S1 C5 C21 102.06(11) . . . . ? O5 S1 C5 C4 39.06(12) . . . . ? O6 S1 C5 C4 170.81(10) . . . . ? N1 S1 C5 C4 -75.44(11) . . . . ? C20 N1 C6 C7 16.13(13) . . . . ? S1 N1 C6 C7 -123.65(10) . . . . ? N1 C6 C7 C15 -28.93(12) . . . . ? N1 C6 C7 C8 -154.23(10) . . . . ? C15 C7 C8 C9 121.82(12) . . . . ? C6 C7 C8 C9 -120.88(13) . . . . ? C15 C7 C8 C14 -58.65(15) . . . . ? C6 C7 C8 C14 58.65(15) . . . . ? C14 C8 C9 C10 -1.28(19) . . . . ? C7 C8 C9 C10 178.24(11) . . . . ? C8 C9 C10 C11 -0.79(19) . . . . ? C9 C10 C11 O1 -177.60(12) . . . . ? C9 C10 C11 C13 1.60(18) . . . . ? C12 O1 C11 C10 -173.15(14) . . . . ? C12 O1 C11 C13 7.56(14) . . . . ? C13 O2 C12 O1 11.96(16) . . . . ? C11 O1 C12 O2 -12.05(16) . . . . ? C12 O2 C13 C14 173.53(14) . . . . ? C12 O2 C13 C11 -7.32(15) . . . . ? C10 C11 C13 C14 -0.3(2) . . . . ? O1 C11 C13 C14 179.01(11) . . . . ? C10 C11 C13 O2 -179.54(11) . . . . ? O1 C11 C13 O2 -0.20(14) . . . . ? O2 C13 C14 C8 177.30(12) . . . . ? C11 C13 C14 C8 -1.75(18) . . . . ? C9 C8 C14 C13 2.50(18) . . . . ? C7 C8 C14 C13 -177.02(11) . . . . ? C8 C7 C15 C16 -17.10(18) . . . . ? C6 C7 C15 C16 -141.67(13) . . . . ? C8 C7 C15 C20 157.22(10) . . . . ? C6 C7 C15 C20 32.64(12) . . . . ? C7 C15 C16 C17 174.83(11) . . . . ? C20 C15 C16 C17 1.22(18) . . . . ? C15 C16 C17 O4 -120.58(12) . . . . ? C15 C16 C17 C18 1.46(16) . . . . ? O4 C17 C18 O3 -35.41(12) . . . . ? C16 C17 C18 O3 -154.94(10) . . . . ? O4 C17 C18 C19 86.30(12) . . . . ? C16 C17 C18 C19 -33.24(13) . . . . ? O3 C18 C19 C20 -178.21(9) . . . . ? C17 C18 C19 C20 61.04(12) . . . . ? C6 N1 C20 C15 3.90(12) . . . . ? S1 N1 C20 C15 145.51(8) . . . . ? C6 N1 C20 C19 124.27(11) . . . . ? S1 N1 C20 C19 -94.12(11) . . . . ? C16 C15 C20 N1 151.27(11) . . . . ? C7 C15 C20 N1 -23.45(12) . . . . ? C16 C15 C20 C19 27.46(16) . . . . ? C7 C15 C20 C19 -147.25(10) . . . . ? C18 C19 C20 N1 -173.26(9) . . . . ? C18 C19 C20 C15 -56.68(12) . . . . ? C4 C5 C21 C22 0.08(19) . . . . ? S1 C5 C21 C22 -177.39(10) . . . . ? C3 C2 C22 C21 -0.7(2) . . . . ? C1 C2 C22 C21 -179.54(12) . . . . ? C5 C21 C22 C2 0.4(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 O3 H3 O4 0.84 1.84 2.6809(13) 174.4 4_566 O4 H4 O1 0.84 2.07 2.8565(13) 155.4 2_544 O4 H4 O3 0.84 2.22 2.6359(12) 110.5 . _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 30.12 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.426 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.054