# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Alves, M. J.' 'Alvares, Yolanda S. P.' 'Azoia, Nuno G.' 'Bickley, J. F.' 'Gilchrist, T.' _publ_contact_author_name 'Dr Maria Jose Alves' _publ_contact_author_address ; Departmento de Quimica Universidade do Minho Campus de Gualtar Braga 4700 320 PORTUGAL ; _publ_contact_author_email 'MJA@QUIMICA.UMINHO.PT' _publ_section_title ; Diastereoselective synthesis of aziridines from (1R)-10-(N,N-dialkylsulfamoyl)isobornyl 2H-azirine-3-carboxylates ; data_na107m _database_code_CSD 184635 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H44 N2 O5 S' _chemical_formula_weight 580.76 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.5114(9) _cell_length_b 10.7109(9) _cell_length_c 12.4297(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.9090(10) _cell_angle_gamma 90.00 _cell_volume 1504.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Needle' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9281 _exptl_absorpt_correction_T_max 0.9703 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9431 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.37 _reflns_number_total 4817 _reflns_number_gt 4384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART' _computing_data_reduction 'SHELXTL (Bruker, 2000)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL97' _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^)+(0.1455P)^2^+0.8881P] 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 0.18(14) _refine_ls_number_reflns 4817 _refine_ls_number_parameters 344 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.2177 _refine_ls_wR_factor_gt 0.2110 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.046 _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 O5 O 0.7890(6) 0.5966(7) 0.5569(5) 0.110(2) Uani 1 1 d . . . C1 C 0.3609(4) 0.9348(3) 0.2651(3) 0.0796(19) Uani 1 1 d GD . . H1 H 0.3683 1.0201 0.2862 0.096 Uiso 1 1 calc R . . C2 C 0.3205(4) 0.9030(4) 0.1560(3) 0.087(2) Uani 1 1 d GD . . H2 H 0.3002 0.9666 0.1025 0.104 Uiso 1 1 calc R . . C3 C 0.3096(4) 0.7782(5) 0.1252(2) 0.0708(18) Uani 1 1 d GD . . H3 H 0.2820 0.7565 0.0507 0.085 Uiso 1 1 calc R . . C4 C 0.3392(5) 0.6851(4) 0.2035(3) 0.094(2) Uani 1 1 d GD . . H4 H 0.3318 0.5997 0.1825 0.113 Uiso 1 1 calc R . . C5 C 0.3796(5) 0.7168(4) 0.3126(3) 0.095(3) Uani 1 1 d GD . . H5 H 0.3998 0.6532 0.3661 0.113 Uiso 1 1 calc R . . C6 C 0.3905(3) 0.8417(4) 0.3434(2) 0.0619(15) Uani 1 1 d GD . . C7 C 0.4403(4) 0.8829(7) 0.4608(4) 0.0616(14) Uani 1 1 d . . . H7 H 0.4657 0.9718 0.4571 0.074 Uiso 1 1 calc R . . C8 C 0.5456(4) 0.8113(9) 0.5153(5) 0.077(2) Uani 1 1 d . . . H8 H 0.5947 0.7733 0.4712 0.092 Uiso 1 1 calc R . . C9 C 0.5733(4) 0.7986(8) 0.6226(4) 0.0689(18) Uani 1 1 d . . . H9 H 0.6418 0.7523 0.6541 0.083 Uiso 1 1 calc R . . C10 C 0.4983(4) 0.8561(5) 0.6957(4) 0.0526(12) Uani 1 1 d . . . H10 H 0.5267 0.9438 0.7103 0.063 Uiso 1 1 calc R . . C11 C 0.51282(19) 0.7904(3) 0.80792(16) 0.0477(11) Uani 1 1 d GU . . C12 C 0.4457(3) 0.6857(3) 0.82142(19) 0.096(2) Uani 1 1 d GU . . H12 H 0.3856 0.6581 0.7631 0.115 Uiso 1 1 calc R . . C13 C 0.4666(4) 0.6213(4) 0.9203(3) 0.114(3) Uani 1 1 d GU . . H13 H 0.4207 0.5497 0.9295 0.137 Uiso 1 1 calc R . . C14 C 0.5546(4) 0.6616(5) 1.0057(2) 0.087(2) Uani 1 1 d GU . . H14 H 0.5688 0.6176 1.0733 0.104 Uiso 1 1 calc R . . C15 C 0.6217(3) 0.7663(5) 0.99219(19) 0.109(4) Uani 1 1 d GU . . H15 H 0.6818 0.7939 1.0505 0.130 Uiso 1 1 calc R . . C16 C 0.6008(3) 0.8307(4) 0.8933(2) 0.097(3) Uani 1 1 d GU . . H16 H 0.6467 0.9023 0.8841 0.116 Uiso 1 1 calc R . . C17 C 0.3716(2) 0.8639(3) 0.63943(19) 0.0389(9) Uani 1 1 d G . . C18 C 0.3147(3) 0.7586(4) 0.56719(18) 0.0429(9) Uani 1 1 d G . . H18A H 0.3649 0.6866 0.5557 0.052 Uiso 1 1 calc R . . H18B H 0.2312 0.7379 0.5688 0.052 Uiso 1 1 calc R . . C19 C 0.2957(3) 0.9437(4) 0.6991(3) 0.0397(9) Uani 1 1 d . . . C20 C 0.1100(3) 0.9577(5) 0.7525(3) 0.0390(8) Uani 1 1 d . . . H20 H 0.1007 1.0463 0.7269 0.047 Uiso 1 1 calc R . . C21 C 0.1466(4) 0.9513(6) 0.8789(3) 0.0480(10) Uani 1 1 d . . . H21A H 0.2201 0.9024 0.9012 0.058 Uiso 1 1 calc R . . H21B H 0.1583 1.0359 0.9112 0.058 Uiso 1 1 calc R . . C22 C 0.0408(4) 0.8856(6) 0.9132(3) 0.0504(11) Uani 1 1 d . . . H22 H 0.0578 0.8496 0.9888 0.061 Uiso 1 1 calc R . . C23 C -0.0607(4) 0.9765(6) 0.8933(3) 0.0560(13) Uani 1 1 d . . . H23A H -0.0355 1.0600 0.9231 0.067 Uiso 1 1 calc R . . H23B H -0.1270 0.9469 0.9270 0.067 Uiso 1 1 calc R . . C24 C -0.0965(4) 0.9802(5) 0.7663(3) 0.0471(11) Uani 1 1 d . . . H24A H -0.1792 0.9519 0.7417 0.056 Uiso 1 1 calc R . . H24B H -0.0879 1.0653 0.7379 0.056 Uiso 1 1 calc R . . C25 C -0.0088(4) 0.8889(4) 0.7286(3) 0.0376(8) Uani 1 1 d . . . C26 C 0.0063(4) 0.7877(5) 0.8209(3) 0.0445(10) Uani 1 1 d . . . C27 C -0.1097(4) 0.7187(6) 0.8265(4) 0.0559(13) Uani 1 1 d . . . H27A H -0.1310 0.6644 0.7624 0.084 Uiso 1 1 calc R . . H27B H -0.1730 0.7797 0.8275 0.084 Uiso 1 1 calc R . . H27C H -0.0990 0.6681 0.8933 0.084 Uiso 1 1 calc R . . C28 C 0.0994(4) 0.6882(5) 0.8160(3) 0.0468(10) Uani 1 1 d . . . H28A H 0.1061 0.6336 0.8801 0.070 Uiso 1 1 calc R . . H28B H 0.1759 0.7283 0.8157 0.070 Uiso 1 1 calc R . . H28C H 0.0763 0.6387 0.7491 0.070 Uiso 1 1 calc R . . C29 C -0.0461(4) 0.8396(4) 0.6122(3) 0.0378(8) Uani 1 1 d . . . H29A H -0.1159 0.7848 0.6097 0.045 Uiso 1 1 calc R . . H29B H 0.0188 0.7876 0.5945 0.045 Uiso 1 1 calc R . . C30 C 0.0214(4) 0.8354(5) 0.3665(3) 0.0458(9) Uani 1 1 d . . . H30A H 0.0306 0.7475 0.3912 0.055 Uiso 1 1 calc R . . H30B H 0.0896 0.8834 0.4065 0.055 Uiso 1 1 calc R . . C31 C 0.0206(5) 0.8418(5) 0.2437(4) 0.0555(12) Uani 1 1 d . . . H31A H -0.0570 0.8154 0.2032 0.083 Uiso 1 1 calc R . . H31B H 0.0819 0.7863 0.2257 0.083 Uiso 1 1 calc R . . H31C H 0.0364 0.9277 0.2234 0.083 Uiso 1 1 calc R . . C32 C -0.1968(4) 0.8130(5) 0.3534(4) 0.0506(11) Uani 1 1 d . . . H32A H -0.2273 0.7817 0.4177 0.061 Uiso 1 1 calc R . . H32B H -0.1762 0.7397 0.3123 0.061 Uiso 1 1 calc R . . C33 C -0.2937(5) 0.8865(8) 0.2805(4) 0.0716(17) Uani 1 1 d . . . H33A H -0.3203 0.9545 0.3228 0.107 Uiso 1 1 calc R . . H33B H -0.3605 0.8311 0.2530 0.107 Uiso 1 1 calc R . . H33C H -0.2630 0.9215 0.2186 0.107 Uiso 1 1 calc R . . N1 N 0.3401(3) 0.8821(4) 0.5198(2) 0.0418(8) Uani 1 1 d . . . N2 N -0.0891(3) 0.8867(4) 0.3919(2) 0.0428(8) Uani 1 1 d . . . O1 O 0.3264(3) 1.0413(3) 0.7421(3) 0.0530(8) Uani 1 1 d . . . O2 O 0.1919(2) 0.8909(3) 0.6978(2) 0.0382(6) Uani 1 1 d . . . O3 O 0.0121(4) 1.0435(3) 0.5204(3) 0.0592(9) Uani 1 1 d . . . O4 O -0.1955(4) 1.0031(4) 0.5138(3) 0.0678(11) Uani 1 1 d . . . S1 S -0.08193(11) 0.95615(10) 0.50941(7) 0.0465(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.115(4) 0.098(5) 0.114(5) -0.019(4) 0.011(3) -0.009(4) C1 0.091(4) 0.068(5) 0.068(3) 0.016(3) -0.015(3) 0.011(3) C2 0.082(4) 0.109(6) 0.062(3) 0.039(4) -0.007(3) 0.014(4) C3 0.068(3) 0.104(6) 0.042(2) -0.005(3) 0.015(2) 0.019(3) C4 0.134(7) 0.082(5) 0.071(4) -0.005(4) 0.028(4) 0.031(5) C5 0.144(7) 0.090(6) 0.057(3) 0.022(4) 0.038(4) 0.043(5) C6 0.064(3) 0.083(4) 0.041(2) 0.024(3) 0.0175(19) 0.023(3) C7 0.055(2) 0.083(4) 0.047(2) 0.022(3) 0.0103(18) -0.007(3) C8 0.041(2) 0.128(7) 0.061(3) 0.028(4) 0.0120(19) 0.005(3) C9 0.035(2) 0.107(5) 0.064(3) 0.024(3) 0.0059(18) -0.003(3) C10 0.040(2) 0.054(3) 0.056(3) 0.010(2) -0.0120(17) -0.009(2) C11 0.0426(19) 0.064(3) 0.0334(18) 0.0074(19) -0.0012(14) 0.020(2) C12 0.137(6) 0.085(5) 0.056(3) 0.015(4) -0.006(3) -0.008(5) C13 0.146(7) 0.123(8) 0.069(4) 0.038(5) 0.006(4) 0.004(7) C14 0.076(4) 0.132(7) 0.051(3) 0.018(4) 0.006(3) 0.047(4) C15 0.077(4) 0.190(10) 0.047(3) -0.034(5) -0.019(3) 0.030(6) C16 0.107(5) 0.117(7) 0.063(4) -0.029(4) 0.008(3) -0.019(5) C17 0.0353(17) 0.048(2) 0.0291(16) 0.0097(16) -0.0036(12) -0.0012(16) C18 0.0398(19) 0.051(3) 0.0367(19) 0.0001(17) 0.0037(14) -0.0024(18) C19 0.0450(19) 0.042(2) 0.0262(15) 0.0048(16) -0.0077(12) 0.0034(17) C20 0.053(2) 0.0330(18) 0.0302(16) -0.0060(18) 0.0049(13) -0.0009(19) C21 0.058(2) 0.055(3) 0.0284(16) -0.012(2) 0.0015(14) -0.009(2) C22 0.060(2) 0.066(3) 0.0246(17) -0.007(2) 0.0071(15) -0.002(2) C23 0.065(3) 0.070(4) 0.0343(19) -0.017(2) 0.0118(17) -0.002(3) C24 0.055(2) 0.050(3) 0.0344(18) -0.0070(18) 0.0047(15) 0.004(2) C25 0.053(2) 0.035(2) 0.0230(15) -0.0028(15) 0.0048(13) -0.0021(17) C26 0.055(2) 0.050(3) 0.0263(16) 0.0045(17) 0.0031(14) -0.006(2) C27 0.060(3) 0.069(4) 0.037(2) 0.010(2) 0.0044(17) -0.016(2) C28 0.064(3) 0.043(2) 0.0324(18) 0.0097(17) 0.0073(16) -0.002(2) C29 0.056(2) 0.0305(19) 0.0238(15) -0.0007(14) -0.0009(13) -0.0009(17) C30 0.068(3) 0.035(2) 0.0335(18) 0.0055(17) 0.0071(16) 0.007(2) C31 0.085(3) 0.047(3) 0.039(2) 0.006(2) 0.023(2) 0.009(2) C32 0.062(2) 0.047(3) 0.041(2) 0.0006(19) 0.0061(17) 0.006(2) C33 0.075(3) 0.087(5) 0.044(2) 0.001(3) -0.010(2) 0.016(3) N1 0.0409(16) 0.053(2) 0.0283(14) 0.0099(15) -0.0007(11) 0.0018(16) N2 0.062(2) 0.037(2) 0.0266(14) 0.0022(14) 0.0009(12) 0.0038(16) O1 0.0523(17) 0.0476(19) 0.0514(17) -0.0072(15) -0.0099(13) -0.0128(15) O2 0.0525(15) 0.0296(15) 0.0330(12) -0.0018(11) 0.0091(10) -0.0048(12) O3 0.109(3) 0.0300(16) 0.0379(16) -0.0019(13) 0.0111(16) -0.0072(18) O4 0.102(3) 0.061(2) 0.0395(17) 0.0006(16) 0.0104(17) 0.029(2) S1 0.0788(7) 0.0309(5) 0.0276(4) 0.0012(4) 0.0044(4) 0.0111(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 C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C6 C7 1.528(6) . ? C7 N1 1.479(6) . ? C7 C8 1.485(8) . ? C8 C9 1.319(7) . ? C9 C10 1.499(8) . ? C10 C17 1.496(4) . ? C10 C11 1.543(5) . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C17 N1 1.476(4) . ? C17 C18 1.5114 . ? C17 C19 1.513(5) . ? C18 N1 1.499(5) . ? C19 O1 1.197(6) . ? C19 O2 1.319(5) . ? C20 O2 1.452(5) . ? C20 C25 1.532(6) . ? C20 C21 1.549(5) . ? C21 C22 1.535(7) . ? C22 C23 1.505(8) . ? C22 C26 1.549(6) . ? C23 C24 1.555(6) . ? C24 C25 1.541(6) . ? C25 C29 1.523(5) . ? C25 C26 1.564(6) . ? C26 C28 1.521(7) . ? C26 C27 1.539(6) . ? C29 S1 1.778(4) . ? C30 N2 1.474(6) . ? C30 C31 1.525(6) . ? C32 N2 1.472(6) . ? C32 C33 1.518(7) . ? N2 S1 1.627(3) . ? O3 S1 1.418(4) . ? O4 S1 1.411(4) . ? 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 C2 C1 C6 120.0 . . ? C1 C2 C3 120.0 . . ? C4 C3 C2 120.0 . . ? C5 C4 C3 120.0 . . ? C4 C5 C6 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 C7 122.6(4) . . ? C1 C6 C7 117.3(4) . . ? N1 C7 C8 114.6(4) . . ? N1 C7 C6 106.5(4) . . ? C8 C7 C6 114.3(6) . . ? C9 C8 C7 122.4(6) . . ? C8 C9 C10 120.9(5) . . ? C17 C10 C9 111.2(4) . . ? C17 C10 C11 112.2(3) . . ? C9 C10 C11 112.6(4) . . ? C12 C11 C16 120.0 . . ? C12 C11 C10 120.6(2) . . ? C16 C11 C10 119.16(19) . . ? C13 C12 C11 120.0 . . ? C12 C13 C14 120.0 . . ? C13 C14 C15 120.0 . . ? C14 C15 C16 120.0 . . ? C15 C16 C11 120.0 . . ? N1 C17 C10 120.7(3) . . ? N1 C17 C18 60.2(2) . . ? C10 C17 C18 120.7(3) . . ? N1 C17 C19 111.4(2) . . ? C10 C17 C19 113.9(3) . . ? C18 C17 C19 119.2(3) . . ? N1 C18 C17 58.70(17) . . ? O1 C19 O2 124.8(4) . . ? O1 C19 C17 124.3(4) . . ? O2 C19 C17 110.9(3) . . ? O2 C20 C25 107.9(3) . . ? O2 C20 C21 112.2(3) . . ? C25 C20 C21 103.7(3) . . ? C22 C21 C20 103.0(3) . . ? C23 C22 C21 106.8(5) . . ? C23 C22 C26 103.5(3) . . ? C21 C22 C26 102.1(3) . . ? C22 C23 C24 103.4(3) . . ? C25 C24 C23 103.3(4) . . ? C29 C25 C20 115.6(3) . . ? C29 C25 C24 115.1(3) . . ? C20 C25 C24 104.4(3) . . ? C29 C25 C26 115.4(4) . . ? C20 C25 C26 102.7(3) . . ? C24 C25 C26 101.8(3) . . ? C28 C26 C27 106.8(4) . . ? C28 C26 C22 114.8(4) . . ? C27 C26 C22 113.2(4) . . ? C28 C26 C25 115.9(3) . . ? C27 C26 C25 112.9(3) . . ? C22 C26 C25 93.0(4) . . ? C25 C29 S1 115.1(3) . . ? N2 C30 C31 110.8(4) . . ? N2 C32 C33 113.3(5) . . ? C17 N1 C7 115.8(3) . . ? C17 N1 C18 61.06(16) . . ? C7 N1 C18 115.4(4) . . ? C32 N2 C30 116.0(4) . . ? C32 N2 S1 115.7(3) . . ? C30 N2 S1 117.6(3) . . ? C19 O2 C20 116.8(3) . . ? O4 S1 O3 117.2(3) . . ? O4 S1 N2 107.9(2) . . ? O3 S1 N2 107.2(2) . . ? O4 S1 C29 108.2(2) . . ? O3 S1 C29 109.0(2) . . ? N2 S1 C29 106.84(19) . . ? 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 C6 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C4 C5 C6 C7 -176.8(4) . . . . ? C2 C1 C6 C5 0.0 . . . . ? C2 C1 C6 C7 176.9(4) . . . . ? C5 C6 C7 N1 -85.7(5) . . . . ? C1 C6 C7 N1 97.4(5) . . . . ? C5 C6 C7 C8 42.0(6) . . . . ? C1 C6 C7 C8 -134.9(5) . . . . ? N1 C7 C8 C9 -30.4(11) . . . . ? C6 C7 C8 C9 -153.8(7) . . . . ? C7 C8 C9 C10 0.4(12) . . . . ? C8 C9 C10 C17 30.0(9) . . . . ? C8 C9 C10 C11 156.9(6) . . . . ? C17 C10 C11 C12 40.5(5) . . . . ? C9 C10 C11 C12 -85.9(4) . . . . ? C17 C10 C11 C16 -144.8(3) . . . . ? C9 C10 C11 C16 88.8(4) . . . . ? C16 C11 C12 C13 0.0 . . . . ? C10 C11 C12 C13 174.6(3) . . . . ? C11 C12 C13 C14 0.0 . . . . ? C12 C13 C14 C15 0.0 . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C11 0.0 . . . . ? C12 C11 C16 C15 0.0 . . . . ? C10 C11 C16 C15 -174.7(3) . . . . ? C9 C10 C17 N1 -31.7(6) . . . . ? C11 C10 C17 N1 -158.9(3) . . . . ? C9 C10 C17 C18 39.7(5) . . . . ? C11 C10 C17 C18 -87.5(4) . . . . ? C9 C10 C17 C19 -168.4(4) . . . . ? C11 C10 C17 C19 64.5(5) . . . . ? C10 C17 C18 N1 -110.2(3) . . . . ? C19 C17 C18 N1 99.3(3) . . . . ? N1 C17 C19 O1 -99.3(4) . . . . ? C10 C17 C19 O1 41.4(5) . . . . ? C18 C17 C19 O1 -166.2(3) . . . . ? N1 C17 C19 O2 81.0(4) . . . . ? C10 C17 C19 O2 -138.3(3) . . . . ? C18 C17 C19 O2 14.1(3) . . . . ? O2 C20 C21 C22 -119.1(4) . . . . ? C25 C20 C21 C22 -3.0(5) . . . . ? C20 C21 C22 C23 -70.3(4) . . . . ? C20 C21 C22 C26 38.0(5) . . . . ? C21 C22 C23 C24 72.0(4) . . . . ? C26 C22 C23 C24 -35.4(5) . . . . ? C22 C23 C24 C25 -0.2(5) . . . . ? O2 C20 C25 C29 -40.0(5) . . . . ? C21 C20 C25 C29 -159.2(4) . . . . ? O2 C20 C25 C24 -167.6(3) . . . . ? C21 C20 C25 C24 73.3(4) . . . . ? O2 C20 C25 C26 86.5(3) . . . . ? C21 C20 C25 C26 -32.6(4) . . . . ? C23 C24 C25 C29 160.6(4) . . . . ? C23 C24 C25 C20 -71.6(4) . . . . ? C23 C24 C25 C26 35.0(4) . . . . ? C23 C22 C26 C28 175.5(4) . . . . ? C21 C22 C26 C28 64.6(5) . . . . ? C23 C22 C26 C27 -61.5(5) . . . . ? C21 C22 C26 C27 -172.3(4) . . . . ? C23 C22 C26 C25 55.1(4) . . . . ? C21 C22 C26 C25 -55.8(4) . . . . ? C29 C25 C26 C28 61.0(5) . . . . ? C20 C25 C26 C28 -65.7(4) . . . . ? C24 C25 C26 C28 -173.6(4) . . . . ? C29 C25 C26 C27 -62.6(5) . . . . ? C20 C25 C26 C27 170.6(4) . . . . ? C24 C25 C26 C27 62.7(5) . . . . ? C29 C25 C26 C22 -179.5(3) . . . . ? C20 C25 C26 C22 53.8(4) . . . . ? C24 C25 C26 C22 -54.1(3) . . . . ? C20 C25 C29 S1 -68.1(4) . . . . ? C24 C25 C29 S1 53.9(5) . . . . ? C26 C25 C29 S1 172.1(3) . . . . ? C10 C17 N1 C7 4.1(6) . . . . ? C18 C17 N1 C7 -106.1(5) . . . . ? C19 C17 N1 C7 141.7(5) . . . . ? C10 C17 N1 C18 110.1(3) . . . . ? C19 C17 N1 C18 -112.3(3) . . . . ? C8 C7 N1 C17 26.6(8) . . . . ? C6 C7 N1 C17 154.1(4) . . . . ? C8 C7 N1 C18 -42.0(7) . . . . ? C6 C7 N1 C18 85.5(4) . . . . ? C17 C18 N1 C7 106.7(3) . . . . ? C33 C32 N2 C30 -123.8(5) . . . . ? C33 C32 N2 S1 92.3(5) . . . . ? C31 C30 N2 C32 68.9(5) . . . . ? C31 C30 N2 S1 -148.0(4) . . . . ? O1 C19 O2 C20 0.2(5) . . . . ? C17 C19 O2 C20 179.9(3) . . . . ? C25 C20 O2 C19 172.9(3) . . . . ? C21 C20 O2 C19 -73.5(5) . . . . ? C32 N2 S1 O4 -39.7(4) . . . . ? C30 N2 S1 O4 177.0(4) . . . . ? C32 N2 S1 O3 -166.8(3) . . . . ? C30 N2 S1 O3 49.9(4) . . . . ? C32 N2 S1 C29 76.4(3) . . . . ? C30 N2 S1 C29 -66.8(4) . . . . ? C25 C29 S1 O4 -76.9(4) . . . . ? C25 C29 S1 O3 51.6(4) . . . . ? C25 C29 S1 N2 167.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.623 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.079 data_y40 _database_code_CSD 184636 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H34 N4 O4 S' _chemical_formula_weight 474.61 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 'Orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 10.1128(13) _cell_length_b 12.9983(16) _cell_length_c 18.399(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2418.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9040 _exptl_absorpt_correction_T_max 0.9584 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'Stoe IPDS' _diffrn_measurement_method 'Image plate' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15465 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.0927 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 24.25 _reflns_number_total 3836 _reflns_number_gt 2448 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE, 1997)' _computing_cell_refinement ? _computing_data_reduction 'X-RED (STOE, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0468P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.10(11) _refine_ls_number_reflns 3836 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1713(5) 1.1270(5) 0.9926(3) 0.0898(19) Uani 1 1 d . . . H1A H 0.0922 1.1531 0.9692 0.108 Uiso 1 1 calc R . . H1B H 0.2147 1.1823 1.0187 0.108 Uiso 1 1 calc R . . H1C H 0.1473 1.0728 1.0264 0.108 Uiso 1 1 calc R . . C2 C 0.2563(5) 1.0880(4) 0.9405(3) 0.0856(19) Uani 1 1 d . . . H2A H 0.2748 1.1429 0.9055 0.103 Uiso 1 1 calc R . . H2B H 0.2095 1.0334 0.9142 0.103 Uiso 1 1 calc R . . C3 C 0.5153(5) 1.0977(4) 1.0736(3) 0.0747(14) Uani 1 1 d . . . H3A H 0.5793 1.1478 1.0906 0.090 Uiso 1 1 calc R . . H3B H 0.5527 1.0292 1.0774 0.090 Uiso 1 1 calc R . . H3C H 0.4360 1.1019 1.1031 0.090 Uiso 1 1 calc R . . C4 C 0.4813(4) 1.1198(3) 0.9958(2) 0.0430(10) Uani 1 1 d . . . H4A H 0.4452 1.1896 0.9923 0.052 Uiso 1 1 calc R . . H4B H 0.5622 1.1173 0.9665 0.052 Uiso 1 1 calc R . . C5 C 0.4871(4) 0.9833(3) 0.8381(2) 0.0317(9) Uani 1 1 d . . . H5A H 0.4172 1.0277 0.8188 0.038 Uiso 1 1 calc R . . H5B H 0.5669 1.0256 0.8430 0.038 Uiso 1 1 calc R . . C6 C 0.5152(3) 0.8992(2) 0.78201(19) 0.0283(9) Uani 1 1 d . . . C7 C 0.3935(4) 0.8329(3) 0.7596(2) 0.0369(10) Uani 1 1 d . . . H7A H 0.3776 0.7776 0.7948 0.044 Uiso 1 1 calc R . . H7B H 0.3136 0.8753 0.7556 0.044 Uiso 1 1 calc R . . C8 C 0.4344(4) 0.7890(3) 0.6849(2) 0.0464(11) Uani 1 1 d . . . H8A H 0.4364 0.7137 0.6858 0.056 Uiso 1 1 calc R . . H8B H 0.3734 0.8117 0.6467 0.056 Uiso 1 1 calc R . . C9 C 0.5728(4) 0.8333(3) 0.6729(2) 0.0386(10) Uani 1 1 d . . . H9 H 0.6025 0.8322 0.6216 0.046 Uiso 1 1 calc R . . C10 C 0.6664(4) 0.7789(3) 0.7256(2) 0.0433(11) Uani 1 1 d . . . H10A H 0.7587 0.7976 0.7160 0.052 Uiso 1 1 calc R . . H10B H 0.6570 0.7040 0.7223 0.052 Uiso 1 1 calc R . . C11 C 0.6208(3) 0.8191(3) 0.8010(2) 0.0309(9) Uani 1 1 d . . . H11 H 0.5815 0.7625 0.8298 0.037 Uiso 1 1 calc R . . C12 C 0.5610(4) 0.9432(3) 0.70610(17) 0.0334(8) Uani 1 1 d . . . C13 C 0.4595(4) 1.0116(3) 0.6687(2) 0.0463(10) Uani 1 1 d . . . H13A H 0.4579 1.0784 0.6922 0.056 Uiso 1 1 calc R . . H13B H 0.3728 0.9801 0.6722 0.056 Uiso 1 1 calc R . . H13C H 0.4832 1.0198 0.6180 0.056 Uiso 1 1 calc R . . C14 C 0.6916(4) 1.0029(3) 0.7078(2) 0.0432(10) Uani 1 1 d . . . H14A H 0.6771 1.0699 0.7297 0.052 Uiso 1 1 calc R . . H14B H 0.7242 1.0117 0.6586 0.052 Uiso 1 1 calc R . . H14C H 0.7561 0.9651 0.7362 0.052 Uiso 1 1 calc R . . C15 C 0.7890(4) 0.8079(3) 0.8915(2) 0.0340(9) Uani 1 1 d . . . C16 C 0.8888(4) 0.8676(3) 0.9332(2) 0.0350(9) Uani 1 1 d . . . C17 C 1.0091(4) 0.8145(3) 0.9600(2) 0.0494(11) Uani 1 1 d . . . H17A H 1.0202 0.7416 0.9477 0.059 Uiso 1 1 calc R . . H17B H 1.0913 0.8542 0.9627 0.059 Uiso 1 1 calc R . . C18 C 0.8215(4) 1.0515(3) 0.9518(2) 0.0411(10) Uani 1 1 d . . . H18 H 0.7743 1.0396 0.9950 0.049 Uiso 1 1 calc R . . C19 C 0.9465(4) 1.0212(3) 0.85578(19) 0.0335(9) Uani 1 1 d . . . C20 C 0.9003(4) 1.1235(3) 0.8574(2) 0.0398(10) Uani 1 1 d . . . C21 C 0.9327(5) 1.1899(3) 0.8010(3) 0.0528(12) Uani 1 1 d . . . H21 H 0.9018 1.2581 0.8003 0.063 Uiso 1 1 calc R . . C22 C 1.0110(5) 1.1526(4) 0.7464(3) 0.0638(14) Uani 1 1 d . . . H22 H 1.0334 1.1962 0.7076 0.077 Uiso 1 1 calc R . . C23 C 1.0587(4) 1.0519(4) 0.7465(2) 0.0615(13) Uani 1 1 d . . . H23 H 1.1135 1.0299 0.7083 0.074 Uiso 1 1 calc R . . C24 C 1.0273(4) 0.9837(3) 0.8015(2) 0.0475(11) Uani 1 1 d . . . H24 H 1.0592 0.9157 0.8019 0.057 Uiso 1 1 calc R . . N1 N 0.3837(3) 1.0460(2) 0.96547(16) 0.0361(7) Uani 1 1 d . . . N2 N 0.9031(4) 0.8419(3) 1.00886(18) 0.0526(10) Uani 1 1 d . . . H2 H 0.8709 0.8425 1.0527 0.063 Uiso 1 1 calc R . . N3 N 0.8946(3) 0.9766(2) 0.91807(17) 0.0320(7) Uani 1 1 d . . . N4 N 0.8224(3) 1.1406(2) 0.9193(2) 0.0462(8) Uani 1 1 d . . . O1 O 0.3293(2) 0.87305(18) 0.91881(15) 0.0451(7) Uani 1 1 d . . . O2 O 0.5550(3) 0.90933(17) 0.96422(13) 0.0416(6) Uani 1 1 d . . . O3 O 0.7297(2) 0.86554(17) 0.84026(13) 0.0319(6) Uani 1 1 d . . . O4 O 0.7660(3) 0.71822(19) 0.90208(16) 0.0519(8) Uani 1 1 d . . . S1 S 0.43899(9) 0.94273(7) 0.92617(5) 0.0353(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.061(3) 0.104(5) 0.104(5) -0.054(4) 0.003(3) 0.003(3) C2 0.053(3) 0.080(4) 0.124(5) -0.047(4) 0.003(3) 0.000(3) C3 0.101(4) 0.076(3) 0.047(3) -0.009(3) -0.009(3) 0.004(3) C4 0.052(3) 0.038(2) 0.040(3) -0.007(2) 0.002(2) -0.001(2) C5 0.037(2) 0.0228(18) 0.035(2) 0.0052(17) -0.0012(17) 0.0038(16) C6 0.037(2) 0.0231(18) 0.025(2) 0.0002(16) -0.0019(16) 0.0002(16) C7 0.037(2) 0.030(2) 0.043(3) 0.0006(19) -0.0069(18) -0.0051(17) C8 0.061(3) 0.035(2) 0.042(3) -0.0072(19) -0.015(2) -0.004(2) C9 0.052(3) 0.033(2) 0.030(2) -0.0040(17) 0.002(2) 0.002(2) C10 0.058(3) 0.025(2) 0.046(3) -0.0072(19) -0.003(2) 0.0061(19) C11 0.038(2) 0.0209(19) 0.033(2) -0.0024(17) -0.0069(18) -0.0046(17) C12 0.046(2) 0.0277(18) 0.026(2) -0.0004(18) -0.0008(19) 0.001(2) C13 0.063(3) 0.038(2) 0.038(2) 0.0019(19) -0.002(2) 0.007(2) C14 0.056(3) 0.036(2) 0.038(2) 0.005(2) 0.005(2) -0.0026(19) C15 0.042(3) 0.032(2) 0.028(2) -0.0034(19) 0.0044(17) 0.0070(19) C16 0.038(2) 0.0306(19) 0.037(2) 0.003(2) -0.0008(19) 0.0018(17) C17 0.045(3) 0.043(2) 0.060(3) 0.009(2) -0.017(2) -0.004(2) C18 0.035(2) 0.045(3) 0.044(3) -0.005(2) -0.0021(18) 0.004(2) C19 0.038(2) 0.030(2) 0.032(2) -0.0002(17) -0.003(2) -0.0116(19) C20 0.043(3) 0.032(2) 0.045(3) 0.003(2) -0.012(2) -0.0051(19) C21 0.063(3) 0.037(2) 0.059(3) 0.013(2) -0.016(3) -0.015(2) C22 0.072(3) 0.067(3) 0.052(3) 0.011(3) -0.003(3) -0.030(3) C23 0.051(3) 0.088(4) 0.045(3) -0.012(3) 0.009(2) -0.022(3) C24 0.051(3) 0.046(2) 0.046(3) -0.006(2) 0.006(2) -0.007(2) N1 0.0355(18) 0.0332(17) 0.0396(18) -0.0093(16) 0.0064(14) 0.0048(15) N2 0.074(3) 0.058(2) 0.026(2) 0.0076(18) -0.0076(18) -0.0050(19) N3 0.0348(18) 0.0274(16) 0.0338(18) 0.0024(16) -0.0009(15) -0.0035(13) N4 0.050(2) 0.0317(19) 0.057(2) -0.001(2) 0.005(2) 0.0011(15) O1 0.0509(16) 0.0355(15) 0.0490(17) 0.0001(14) 0.0106(15) -0.0138(13) O2 0.0508(16) 0.0427(15) 0.0314(14) 0.0064(12) -0.0006(14) 0.0082(13) O3 0.0401(15) 0.0259(13) 0.0296(14) 0.0023(12) -0.0044(12) -0.0006(11) O4 0.0649(19) 0.0246(14) 0.066(2) 0.0090(14) -0.0197(15) -0.0044(13) S1 0.0440(5) 0.0273(5) 0.0346(5) 0.0013(5) 0.0063(5) -0.0003(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 C1 C2 1.384(6) . ? C2 N1 1.473(6) . ? C3 C4 1.500(6) . ? C4 N1 1.485(5) . ? C5 C6 1.530(5) . ? C5 S1 1.772(4) . ? C6 C11 1.532(5) . ? C6 C7 1.559(5) . ? C6 C12 1.578(5) . ? C7 C8 1.545(5) . ? C8 C9 1.529(6) . ? C9 C10 1.528(5) . ? C9 C12 1.558(5) . ? C10 C11 1.552(5) . ? C11 O3 1.449(4) . ? C12 C13 1.522(5) . ? C12 C14 1.532(5) . ? C15 O4 1.204(4) . ? C15 O3 1.345(4) . ? C15 C16 1.487(5) . ? C16 N2 1.438(5) . ? C16 N3 1.445(4) . ? C16 C17 1.483(5) . ? C17 N2 1.444(5) . ? C18 N4 1.303(5) . ? C18 N3 1.371(5) . ? C19 C24 1.379(5) . ? C19 N3 1.388(5) . ? C19 C20 1.409(5) . ? C20 C21 1.390(5) . ? C20 N4 1.403(5) . ? C21 C22 1.368(6) . ? C22 C23 1.394(6) . ? C23 C24 1.382(6) . ? N1 S1 1.624(3) . ? O1 S1 1.438(3) . ? O2 S1 1.434(3) . ? 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 C1 C2 N1 117.6(5) . . ? N1 C4 C3 112.8(3) . . ? C6 C5 S1 117.1(2) . . ? C5 C6 C11 117.5(3) . . ? C5 C6 C7 115.3(3) . . ? C11 C6 C7 103.6(3) . . ? C5 C6 C12 113.1(3) . . ? C11 C6 C12 104.1(3) . . ? C7 C6 C12 101.4(3) . . ? C8 C7 C6 103.2(3) . . ? C9 C8 C7 103.5(3) . . ? C10 C9 C8 107.6(3) . . ? C10 C9 C12 102.9(3) . . ? C8 C9 C12 102.6(3) . . ? C9 C10 C11 103.1(3) . . ? O3 C11 C6 111.1(3) . . ? O3 C11 C10 111.1(3) . . ? C6 C11 C10 103.4(3) . . ? C13 C12 C14 107.1(3) . . ? C13 C12 C9 114.2(3) . . ? C14 C12 C9 114.0(3) . . ? C13 C12 C6 114.4(3) . . ? C14 C12 C6 114.7(3) . . ? C9 C12 C6 92.1(3) . . ? O4 C15 O3 124.5(3) . . ? O4 C15 C16 123.6(3) . . ? O3 C15 C16 111.9(3) . . ? N2 C16 N3 114.2(3) . . ? N2 C16 C17 59.2(3) . . ? N3 C16 C17 119.1(3) . . ? N2 C16 C15 116.6(3) . . ? N3 C16 C15 116.1(3) . . ? C17 C16 C15 119.0(3) . . ? N2 C17 C16 58.8(3) . . ? N4 C18 N3 114.8(4) . . ? C24 C19 N3 132.3(3) . . ? C24 C19 C20 123.0(4) . . ? N3 C19 C20 104.6(3) . . ? C21 C20 N4 129.8(4) . . ? C21 C20 C19 119.5(4) . . ? N4 C20 C19 110.7(3) . . ? C22 C21 C20 117.6(4) . . ? C21 C22 C23 122.2(4) . . ? C24 C23 C22 121.6(4) . . ? C19 C24 C23 116.0(4) . . ? C2 N1 C4 117.3(3) . . ? C2 N1 S1 117.9(3) . . ? C4 N1 S1 118.2(2) . . ? C16 N2 C17 61.9(3) . . ? C18 N3 C19 106.3(3) . . ? C18 N3 C16 126.0(3) . . ? C19 N3 C16 125.8(3) . . ? C18 N4 C20 103.6(3) . . ? C15 O3 C11 117.1(3) . . ? O2 S1 O1 119.11(16) . . ? O2 S1 N1 108.34(15) . . ? O1 S1 N1 107.27(16) . . ? O2 S1 C5 108.17(16) . . ? O1 S1 C5 108.25(17) . . ? N1 S1 C5 104.81(16) . . ? 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 S1 C5 C6 C11 -57.1(4) . . . . ? S1 C5 C6 C7 65.5(4) . . . . ? S1 C5 C6 C12 -178.4(2) . . . . ? C5 C6 C7 C8 158.0(3) . . . . ? C11 C6 C7 C8 -72.3(3) . . . . ? C12 C6 C7 C8 35.5(3) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C10 71.2(3) . . . . ? C7 C8 C9 C12 -36.9(3) . . . . ? C8 C9 C10 C11 -68.4(3) . . . . ? C12 C9 C10 C11 39.5(4) . . . . ? C5 C6 C11 O3 -37.2(4) . . . . ? C7 C6 C11 O3 -165.6(3) . . . . ? C12 C6 C11 O3 88.7(3) . . . . ? C5 C6 C11 C10 -156.5(3) . . . . ? C7 C6 C11 C10 75.1(3) . . . . ? C12 C6 C11 C10 -30.6(3) . . . . ? C9 C10 C11 O3 -124.4(3) . . . . ? C9 C10 C11 C6 -5.1(4) . . . . ? C10 C9 C12 C13 -173.3(3) . . . . ? C8 C9 C12 C13 -61.7(4) . . . . ? C10 C9 C12 C14 63.1(4) . . . . ? C8 C9 C12 C14 174.7(3) . . . . ? C10 C9 C12 C6 -55.2(3) . . . . ? C8 C9 C12 C6 56.4(3) . . . . ? C5 C6 C12 C13 -61.5(4) . . . . ? C11 C6 C12 C13 169.9(3) . . . . ? C7 C6 C12 C13 62.6(3) . . . . ? C5 C6 C12 C14 62.9(4) . . . . ? C11 C6 C12 C14 -65.7(4) . . . . ? C7 C6 C12 C14 -173.0(3) . . . . ? C5 C6 C12 C9 -179.3(3) . . . . ? C11 C6 C12 C9 52.0(3) . . . . ? C7 C6 C12 C9 -55.3(3) . . . . ? O4 C15 C16 N2 -35.2(5) . . . . ? O3 C15 C16 N2 145.6(3) . . . . ? O4 C15 C16 N3 -174.3(3) . . . . ? O3 C15 C16 N3 6.6(4) . . . . ? O4 C15 C16 C17 32.6(6) . . . . ? O3 C15 C16 C17 -146.5(3) . . . . ? N3 C16 C17 N2 102.4(4) . . . . ? C15 C16 C17 N2 -105.4(4) . . . . ? C24 C19 C20 C21 2.4(6) . . . . ? N3 C19 C20 C21 -178.7(3) . . . . ? C24 C19 C20 N4 -178.9(3) . . . . ? N3 C19 C20 N4 0.1(4) . . . . ? N4 C20 C21 C22 -179.6(4) . . . . ? C19 C20 C21 C22 -1.2(6) . . . . ? C20 C21 C22 C23 -0.5(7) . . . . ? C21 C22 C23 C24 1.1(7) . . . . ? N3 C19 C24 C23 179.6(4) . . . . ? C20 C19 C24 C23 -1.8(6) . . . . ? C22 C23 C24 C19 0.0(6) . . . . ? C1 C2 N1 C4 -67.9(6) . . . . ? C1 C2 N1 S1 141.0(4) . . . . ? C3 C4 N1 C2 118.6(4) . . . . ? C3 C4 N1 S1 -90.3(4) . . . . ? N3 C16 N2 C17 -110.7(4) . . . . ? C15 C16 N2 C17 109.5(4) . . . . ? N4 C18 N3 C19 -1.5(4) . . . . ? N4 C18 N3 C16 -166.2(3) . . . . ? C24 C19 N3 C18 179.6(4) . . . . ? C20 C19 N3 C18 0.8(4) . . . . ? C24 C19 N3 C16 -15.7(6) . . . . ? C20 C19 N3 C16 165.5(3) . . . . ? N2 C16 N3 C18 -51.5(5) . . . . ? C17 C16 N3 C18 -118.5(4) . . . . ? C15 C16 N3 C18 88.5(4) . . . . ? N2 C16 N3 C19 146.7(3) . . . . ? C17 C16 N3 C19 79.7(5) . . . . ? C15 C16 N3 C19 -73.3(4) . . . . ? N3 C18 N4 C20 1.5(4) . . . . ? C21 C20 N4 C18 177.7(4) . . . . ? C19 C20 N4 C18 -0.9(4) . . . . ? O4 C15 O3 C11 7.2(5) . . . . ? C16 C15 O3 C11 -173.7(3) . . . . ? C6 C11 O3 C15 145.6(3) . . . . ? C10 C11 O3 C15 -99.8(3) . . . . ? C2 N1 S1 O2 -173.5(3) . . . . ? C4 N1 S1 O2 35.6(3) . . . . ? C2 N1 S1 O1 -43.7(4) . . . . ? C4 N1 S1 O1 165.3(3) . . . . ? C2 N1 S1 C5 71.2(4) . . . . ? C4 N1 S1 C5 -79.7(3) . . . . ? C6 C5 S1 O2 77.7(3) . . . . ? C6 C5 S1 O1 -52.7(3) . . . . ? C6 C5 S1 N1 -166.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 24.25 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.619 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.047 data_za155 _database_code_CSD 184637 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H33 N3 O5 S' _chemical_formula_weight 451.57 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.0165(15) _cell_length_b 12.3521(15) _cell_length_c 10.5145(16) _cell_angle_alpha 90.00 _cell_angle_beta 115.807(16) _cell_angle_gamma 90.00 _cell_volume 1171.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9021 _exptl_absorpt_correction_T_max 0.9493 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'Stoe IPDS' _diffrn_measurement_method 'Image plate' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7463 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.24 _reflns_number_total 3673 _reflns_number_gt 2856 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE, 1997)' _computing_cell_refinement ? _computing_data_reduction 'X-RED (STOE, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(8) _refine_ls_number_reflns 3673 _refine_ls_number_parameters 284 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_restrained_S_all 0.915 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1937(3) 1.1295(2) 0.2915(3) 0.0499(8) Uani 1 1 d . . . H1A H 0.1575 1.1611 0.1969 0.060 Uiso 1 1 calc R . . H1B H 0.1167 1.0986 0.3144 0.060 Uiso 1 1 calc R . . C2 C 0.3404(3) 1.0764(2) 0.3511(3) 0.0363(6) Uani 1 1 d . . . C3 C 0.4620(3) 0.9919(3) 0.5879(3) 0.0512(7) Uani 1 1 d . . . H3 H 0.5195 1.0520 0.6358 0.061 Uiso 1 1 calc R . . C4 C 0.4598(4) 0.8944(3) 0.6471(4) 0.0657(10) Uani 1 1 d . . . H4 H 0.5150 0.8751 0.7424 0.079 Uiso 1 1 calc R . . C5 C 0.3618(4) 0.8290(3) 0.5417(4) 0.0607(9) Uani 1 1 d . . . H5 H 0.3378 0.7571 0.5526 0.073 Uiso 1 1 calc R . . C6 C 0.3052(3) 0.8868(2) 0.4179(3) 0.0452(7) Uani 1 1 d . . . C7 C 0.2085(4) 0.8487(3) 0.2808(5) 0.0649(10) Uani 1 1 d . . . H7 H 0.1701 0.7786 0.2761 0.078 Uiso 1 1 calc R . . C8 C 0.4255(3) 1.0769(2) 0.2639(3) 0.0339(6) Uani 1 1 d . . . C9 C 0.6035(3) 0.9888(2) 0.2099(2) 0.0327(6) Uani 1 1 d . . . H9 H 0.6487 1.0607 0.2136 0.039 Uiso 1 1 calc R . . C10 C 0.5146(3) 0.9519(2) 0.0554(3) 0.0443(7) Uani 1 1 d . . . H10A H 0.4117 0.9352 0.0355 0.053 Uiso 1 1 calc R . . H10B H 0.5151 1.0077 -0.0105 0.053 Uiso 1 1 calc R . . C11 C 0.5957(3) 0.8509(2) 0.0448(3) 0.0461(7) Uani 1 1 d . . . H11 H 0.5364 0.8034 -0.0360 0.055 Uiso 1 1 calc R . . C12 C 0.7434(4) 0.8876(3) 0.0486(3) 0.0654(10) Uani 1 1 d . . . H12A H 0.7288 0.9462 -0.0190 0.078 Uiso 1 1 calc R . . H12B H 0.7949 0.8274 0.0283 0.078 Uiso 1 1 calc R . . C13 C 0.8298(3) 0.9276(3) 0.2030(3) 0.0552(9) Uani 1 1 d . . . H13A H 0.8500 1.0055 0.2059 0.066 Uiso 1 1 calc R . . H13B H 0.9239 0.8887 0.2514 0.066 Uiso 1 1 calc R . . C14 C 0.7232(3) 0.9021(2) 0.2714(3) 0.0340(6) Uani 1 1 d . . . C15 C 0.6435(3) 0.7973(2) 0.1903(3) 0.0397(7) Uani 1 1 d . . . C16 C 0.7484(4) 0.7010(3) 0.2179(4) 0.0677(10) Uani 1 1 d . . . H16A H 0.6930 0.6387 0.1649 0.081 Uiso 1 1 calc R . . H16B H 0.7940 0.6840 0.3179 0.081 Uiso 1 1 calc R . . H16C H 0.8249 0.7191 0.1883 0.081 Uiso 1 1 calc R . . C17 C 0.5130(4) 0.7578(2) 0.2159(3) 0.0469(7) Uani 1 1 d . . . H17A H 0.4716 0.6930 0.1607 0.056 Uiso 1 1 calc R . . H17B H 0.4376 0.8137 0.1880 0.056 Uiso 1 1 calc R . . H17C H 0.5467 0.7416 0.3154 0.056 Uiso 1 1 calc R . . C18 C 0.7988(3) 0.8902(2) 0.4321(3) 0.0374(6) Uani 1 1 d . . . H18A H 0.8671 0.8286 0.4558 0.045 Uiso 1 1 calc R . . H18B H 0.7226 0.8720 0.4635 0.045 Uiso 1 1 calc R . . C19 C 0.9077(4) 0.9652(3) 0.7852(4) 0.0719(11) Uani 1 1 d . . . H19A H 0.9241 0.8961 0.8355 0.086 Uiso 1 1 calc R . . H19B H 0.8007 0.9738 0.7278 0.086 Uiso 1 1 calc R . . C20 C 0.9638(6) 1.0562(4) 0.8910(4) 0.0901(14) Uani 1 1 d . . . H20A H 0.9137 1.0542 0.9518 0.108 Uiso 1 1 calc R . . H20B H 0.9441 1.1250 0.8415 0.108 Uiso 1 1 calc R . . H20C H 1.0697 1.0481 0.9477 0.108 Uiso 1 1 calc R . . C21 C 1.1312(3) 0.9150(3) 0.7450(4) 0.0672(10) Uani 1 1 d . . . H21A H 1.1941 0.9484 0.8362 0.081 Uiso 1 1 calc R . . H21B H 1.1739 0.9328 0.6796 0.081 Uiso 1 1 calc R . . C22 C 1.1361(5) 0.7953(3) 0.7639(5) 0.0949(14) Uani 1 1 d . . . H22A H 1.2380 0.7705 0.8007 0.114 Uiso 1 1 calc R . . H22B H 1.0778 0.7609 0.6735 0.114 Uiso 1 1 calc R . . H22C H 1.0956 0.7764 0.8296 0.114 Uiso 1 1 calc R . . N1 N 0.3221(3) 1.1808(2) 0.4064(3) 0.0485(7) Uani 1 1 d . . . H1 H 0.362(4) 1.231(3) 0.378(3) 0.059(11) Uiso 1 1 d . . . N2 N 0.3676(2) 0.98803(18) 0.4485(2) 0.0363(5) Uani 1 1 d . . . N3 N 0.9832(3) 0.9632(2) 0.6915(2) 0.0551(7) Uani 1 1 d . . . O1 O 0.1698(2) 0.8956(2) 0.1694(3) 0.0717(7) Uani 1 1 d . . . O2 O 0.4151(3) 1.14953(16) 0.1844(2) 0.0549(6) Uani 1 1 d . . . O3 O 0.51155(17) 0.99048(14) 0.28654(15) 0.0307(4) Uani 1 1 d . . . O4 O 0.7920(3) 1.0831(2) 0.5236(3) 0.0878(8) Uani 1 1 d . . . O5 O 1.0104(3) 1.0306(2) 0.4852(2) 0.0815(9) Uani 1 1 d . . . S1 S 0.89898(8) 1.00355(6) 0.53072(7) 0.0511(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0436(19) 0.0549(19) 0.051(2) 0.0067(15) 0.0202(16) 0.0126(16) C2 0.0440(16) 0.0325(14) 0.0355(15) 0.0007(12) 0.0202(13) 0.0036(13) C3 0.0639(18) 0.0550(18) 0.0366(16) -0.0023(17) 0.0236(15) 0.0060(19) C4 0.097(3) 0.062(2) 0.0512(19) 0.0176(19) 0.044(2) 0.024(2) C5 0.076(3) 0.0467(19) 0.082(3) 0.0193(19) 0.056(2) 0.0131(18) C6 0.0435(17) 0.0388(17) 0.066(2) 0.0015(16) 0.0362(17) 0.0015(15) C7 0.043(2) 0.059(2) 0.093(3) -0.014(2) 0.030(2) -0.0056(17) C8 0.0417(16) 0.0296(14) 0.0286(13) -0.0025(12) 0.0138(12) 0.0030(13) C9 0.0339(13) 0.0407(14) 0.0275(12) 0.0048(12) 0.0172(11) -0.0006(13) C10 0.0530(18) 0.0517(17) 0.0273(14) 0.0071(12) 0.0166(14) 0.0015(14) C11 0.0496(18) 0.0609(19) 0.0307(14) -0.0078(13) 0.0202(14) -0.0020(15) C12 0.065(2) 0.098(3) 0.0511(18) -0.0119(19) 0.0414(17) -0.006(2) C13 0.0403(17) 0.087(2) 0.0490(18) -0.0117(17) 0.0291(15) -0.0048(17) C14 0.0302(13) 0.0470(16) 0.0283(13) -0.0021(12) 0.0158(12) 0.0005(13) C15 0.0421(16) 0.0413(15) 0.0341(15) -0.0040(12) 0.0150(13) 0.0076(13) C16 0.069(2) 0.061(2) 0.065(2) -0.0151(18) 0.0214(19) 0.0188(19) C17 0.058(2) 0.0405(15) 0.0406(16) -0.0013(13) 0.0197(15) -0.0057(14) C18 0.0309(15) 0.0457(16) 0.0303(13) 0.0009(13) 0.0082(12) 0.0037(13) C19 0.077(2) 0.093(3) 0.054(2) -0.0102(19) 0.0362(19) -0.021(2) C20 0.139(4) 0.089(3) 0.057(2) -0.006(2) 0.057(3) -0.021(3) C21 0.0450(19) 0.072(2) 0.067(2) 0.0035(18) 0.0082(17) -0.0130(18) C22 0.074(3) 0.077(3) 0.112(4) 0.014(2) 0.021(3) 0.001(2) N1 0.0623(18) 0.0353(14) 0.0559(17) -0.0023(12) 0.0331(15) 0.0075(14) N2 0.0430(12) 0.0354(12) 0.0383(12) -0.0005(11) 0.0252(11) 0.0037(12) N3 0.0358(13) 0.094(2) 0.0269(12) -0.0013(12) 0.0058(11) -0.0066(13) O1 0.0504(13) 0.0834(17) 0.0654(16) -0.0227(15) 0.0104(13) 0.0039(14) O2 0.0836(15) 0.0428(11) 0.0546(12) 0.0190(10) 0.0451(12) 0.0198(11) O3 0.0319(8) 0.0331(9) 0.0309(9) 0.0047(8) 0.0174(7) 0.0047(9) O4 0.0909(18) 0.0646(16) 0.0682(16) -0.0228(14) -0.0024(14) 0.0239(16) O5 0.0870(18) 0.109(2) 0.0507(12) -0.0089(13) 0.0321(13) -0.0518(16) S1 0.0517(4) 0.0540(5) 0.0351(4) -0.0043(4) 0.0071(3) -0.0080(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 C1 N1 1.471(4) . ? C1 C2 1.477(4) . ? C2 N2 1.439(3) . ? C2 N1 1.459(3) . ? C2 C8 1.498(3) . ? C3 N2 1.356(3) . ? C3 C4 1.360(4) . ? C4 C5 1.378(5) . ? C5 C6 1.372(4) . ? C6 N2 1.372(4) . ? C6 C7 1.422(5) . ? C7 O1 1.210(4) . ? C8 O2 1.199(3) . ? C8 O3 1.327(3) . ? C9 O3 1.465(3) . ? C9 C14 1.526(4) . ? C9 C10 1.542(3) . ? C10 C11 1.519(4) . ? C11 C12 1.531(4) . ? C11 C15 1.539(4) . ? C12 C13 1.551(4) . ? C13 C14 1.557(4) . ? C14 C18 1.528(3) . ? C14 C15 1.564(4) . ? C15 C17 1.526(4) . ? C15 C16 1.529(4) . ? C18 S1 1.771(3) . ? C19 N3 1.481(4) . ? C19 C20 1.508(5) . ? C21 N3 1.463(4) . ? C21 C22 1.491(5) . ? N3 S1 1.605(2) . ? O4 S1 1.432(3) . ? O5 S1 1.432(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 59.33(18) . . ? N2 C2 N1 113.8(2) . . ? N2 C2 C1 118.9(2) . . ? N1 C2 C1 60.11(19) . . ? N2 C2 C8 117.2(2) . . ? N1 C2 C8 116.3(2) . . ? C1 C2 C8 117.7(2) . . ? N2 C3 C4 108.7(3) . . ? C3 C4 C5 107.4(3) . . ? C6 C5 C4 108.3(3) . . ? C5 C6 N2 107.1(3) . . ? C5 C6 C7 127.4(3) . . ? N2 C6 C7 125.4(3) . . ? O1 C7 C6 127.8(3) . . ? O2 C8 O3 125.4(2) . . ? O2 C8 C2 122.0(2) . . ? O3 C8 C2 112.6(2) . . ? O3 C9 C14 110.05(19) . . ? O3 C9 C10 111.73(19) . . ? C14 C9 C10 103.1(2) . . ? C11 C10 C9 103.8(2) . . ? C10 C11 C12 107.2(3) . . ? C10 C11 C15 103.0(2) . . ? C12 C11 C15 102.9(2) . . ? C11 C12 C13 102.4(2) . . ? C12 C13 C14 103.7(2) . . ? C9 C14 C18 117.1(2) . . ? C9 C14 C13 103.4(2) . . ? C18 C14 C13 114.9(2) . . ? C9 C14 C15 103.3(2) . . ? C18 C14 C15 114.4(2) . . ? C13 C14 C15 101.9(2) . . ? C17 C15 C16 106.8(3) . . ? C17 C15 C11 113.1(2) . . ? C16 C15 C11 114.5(2) . . ? C17 C15 C14 116.2(2) . . ? C16 C15 C14 113.3(2) . . ? C11 C15 C14 92.9(2) . . ? C14 C18 S1 116.92(19) . . ? N3 C19 C20 111.7(3) . . ? N3 C21 C22 115.1(3) . . ? C2 N1 C1 60.56(18) . . ? C3 N2 C6 108.5(2) . . ? C3 N2 C2 124.7(2) . . ? C6 N2 C2 126.8(2) . . ? C21 N3 C19 118.4(3) . . ? C21 N3 S1 120.8(2) . . ? C19 N3 S1 120.6(2) . . ? C8 O3 C9 115.34(19) . . ? O4 S1 O5 119.78(19) . . ? O4 S1 N3 107.88(15) . . ? O5 S1 N3 107.17(13) . . ? O4 S1 C18 106.97(14) . . ? O5 S1 C18 108.31(13) . . ? N3 S1 C18 105.96(14) . . ? 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 N1 C1 C2 N2 102.4(3) . . . . ? N1 C1 C2 C8 -106.1(3) . . . . ? N2 C3 C4 C5 0.0(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 N2 -0.7(3) . . . . ? C4 C5 C6 C7 175.1(3) . . . . ? C5 C6 C7 O1 -172.0(3) . . . . ? N2 C6 C7 O1 3.1(5) . . . . ? N2 C2 C8 O2 -176.7(3) . . . . ? N1 C2 C8 O2 -37.2(4) . . . . ? C1 C2 C8 O2 31.2(4) . . . . ? N2 C2 C8 O3 2.6(3) . . . . ? N1 C2 C8 O3 142.2(2) . . . . ? C1 C2 C8 O3 -149.4(2) . . . . ? O3 C9 C10 C11 -119.8(2) . . . . ? C14 C9 C10 C11 -1.7(2) . . . . ? C9 C10 C11 C12 -71.5(3) . . . . ? C9 C10 C11 C15 36.6(3) . . . . ? C10 C11 C12 C13 69.3(3) . . . . ? C15 C11 C12 C13 -38.9(3) . . . . ? C11 C12 C13 C14 3.3(3) . . . . ? O3 C9 C14 C18 -40.5(3) . . . . ? C10 C9 C14 C18 -159.8(2) . . . . ? O3 C9 C14 C13 -167.9(2) . . . . ? C10 C9 C14 C13 72.8(2) . . . . ? O3 C9 C14 C15 86.2(2) . . . . ? C10 C9 C14 C15 -33.1(2) . . . . ? C12 C13 C14 C9 -74.5(3) . . . . ? C12 C13 C14 C18 156.6(3) . . . . ? C12 C13 C14 C15 32.4(3) . . . . ? C10 C11 C15 C17 65.9(3) . . . . ? C12 C11 C15 C17 177.3(2) . . . . ? C10 C11 C15 C16 -171.5(3) . . . . ? C12 C11 C15 C16 -60.1(3) . . . . ? C10 C11 C15 C14 -54.2(2) . . . . ? C12 C11 C15 C14 57.1(3) . . . . ? C9 C14 C15 C17 -64.4(3) . . . . ? C18 C14 C15 C17 64.0(3) . . . . ? C13 C14 C15 C17 -171.4(2) . . . . ? C9 C14 C15 C16 171.4(2) . . . . ? C18 C14 C15 C16 -60.2(3) . . . . ? C13 C14 C15 C16 64.4(3) . . . . ? C9 C14 C15 C11 53.2(2) . . . . ? C18 C14 C15 C11 -178.4(2) . . . . ? C13 C14 C15 C11 -53.8(2) . . . . ? C9 C14 C18 S1 -62.0(3) . . . . ? C13 C14 C18 S1 59.7(3) . . . . ? C15 C14 C18 S1 177.01(18) . . . . ? N2 C2 N1 C1 -110.8(3) . . . . ? C8 C2 N1 C1 108.3(3) . . . . ? C4 C3 N2 C6 -0.5(3) . . . . ? C4 C3 N2 C2 180.0(2) . . . . ? C5 C6 N2 C3 0.7(3) . . . . ? C7 C6 N2 C3 -175.2(3) . . . . ? C5 C6 N2 C2 -179.8(2) . . . . ? C7 C6 N2 C2 4.4(4) . . . . ? N1 C2 N2 C3 -43.8(3) . . . . ? C1 C2 N2 C3 -111.6(3) . . . . ? C8 C2 N2 C3 96.8(3) . . . . ? N1 C2 N2 C6 136.7(3) . . . . ? C1 C2 N2 C6 69.0(3) . . . . ? C8 C2 N2 C6 -82.7(3) . . . . ? C22 C21 N3 C19 69.6(4) . . . . ? C22 C21 N3 S1 -105.2(4) . . . . ? C20 C19 N3 C21 79.7(4) . . . . ? C20 C19 N3 S1 -105.5(3) . . . . ? O2 C8 O3 C9 2.3(4) . . . . ? C2 C8 O3 C9 -177.00(19) . . . . ? C14 C9 O3 C8 165.8(2) . . . . ? C10 C9 O3 C8 -80.3(3) . . . . ? C21 N3 S1 O4 -156.8(3) . . . . ? C19 N3 S1 O4 28.5(3) . . . . ? C21 N3 S1 O5 -26.6(3) . . . . ? C19 N3 S1 O5 158.7(3) . . . . ? C21 N3 S1 C18 88.9(3) . . . . ? C19 N3 S1 C18 -85.8(3) . . . . ? C14 C18 S1 O4 72.6(2) . . . . ? C14 C18 S1 O5 -57.8(2) . . . . ? C14 C18 S1 N3 -172.52(19) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 24.24 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.140 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.035