# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Chimin Chau' _publ_contact_author_email CMCHAU@CSMU.EDU.TW _publ_section_title ; Diels-Alder reactions of 1,2,6,6a-tetrahydro-1-tosyl-cyclopenta[b]pyrrol-3(5H)-one, 1,2,3,6,7,7a-hexahydro-4H-1-tosyl-cyclopenta[b]pyridin-4-one and 1,2,5,6,7,7a-hexahydro-3H-1-tosyl-indol-3-one: an efficient method to novel nitrogen-containing angular tricyclic skeleton ; _publ_author_name 'Chimin Chau.' # Attachment 'AP16M.CIF-compound 38' data_ap16m _database_code_depnum_ccdc_archive 'CCDC 678651' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H23 N O3 S' _chemical_formula_weight 357.45 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8582(5) _cell_length_b 10.1699(7) _cell_length_c 11.6933(8) _cell_angle_alpha 101.7670(10) _cell_angle_beta 103.3140(10) _cell_angle_gamma 98.3220(10) _cell_volume 872.06(10) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3257 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Tabular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.88863 _exptl_absorpt_correction_T_max 0.96682 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 9136 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4095 _reflns_number_gt 2893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0749P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4095 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.055 _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 0.37674(6) 0.35262(5) 0.76563(5) 0.03622(16) Uani 1 1 d . . . N1 N 0.43065(19) 0.22367(16) 0.81712(13) 0.0332(4) Uani 1 1 d . . . O1 O 0.7095(2) 0.11564(18) 1.04386(13) 0.0583(4) Uani 1 1 d . . . O2 O 0.32648(19) 0.43827(16) 0.86025(14) 0.0498(4) Uani 1 1 d . . . O3 O 0.25399(18) 0.29851(16) 0.64835(13) 0.0486(4) Uani 1 1 d . . . C1 C 0.9777(3) 0.1004(2) 0.8717(2) 0.0488(6) Uani 1 1 d . . . C2 C 0.8372(2) 0.1757(2) 0.81555(19) 0.0409(5) Uani 1 1 d D . . C3 C 0.8397(3) 0.1333(3) 0.6844(2) 0.0513(6) Uani 1 1 d . . . C4 C 0.8648(3) 0.0062(3) 0.6629(2) 0.0547(6) Uani 1 1 d . . . C5 C 0.8868(3) -0.0368(2) 0.7808(2) 0.0468(5) Uani 1 1 d . . . C6 C 0.7006(3) -0.0579(2) 0.80810(18) 0.0370(4) Uani 1 1 d . . . C7 C 0.5546(3) -0.1745(2) 0.7181(2) 0.0464(5) Uani 1 1 d . . . C8 C 0.4211(3) -0.1295(2) 0.62542(19) 0.0427(5) Uani 1 1 d . . . C9 C 0.3455(2) -0.0149(2) 0.68774(17) 0.0378(5) Uani 1 1 d . . . C10 C 0.4914(2) 0.11291(19) 0.74077(15) 0.0296(4) Uani 1 1 d . . . C11 C 0.6615(2) 0.09034(18) 0.82609(16) 0.0305(4) Uani 1 1 d D . . C12 C 0.6370(2) 0.1432(2) 0.95151(17) 0.0366(4) Uani 1 1 d . . . C13 C 0.5083(3) 0.2395(2) 0.94681(17) 0.0409(5) Uani 1 1 d . . . C14 C 0.5715(3) 0.44255(19) 0.74386(18) 0.0356(4) Uani 1 1 d . . . C15 C 0.7076(3) 0.5233(2) 0.84188(18) 0.0430(5) Uani 1 1 d . . . C16 C 0.8645(3) 0.5833(2) 0.8230(2) 0.0469(5) Uani 1 1 d . . . C17 C 0.8884(3) 0.5666(2) 0.7070(2) 0.0460(5) Uani 1 1 d . . . C18 C 0.7493(3) 0.4886(2) 0.6105(2) 0.0508(6) Uani 1 1 d . . . C19 C 0.5919(3) 0.4252(2) 0.62730(19) 0.0439(5) Uani 1 1 d . . . C20 C 1.0607(4) 0.6289(3) 0.6859(3) 0.0675(7) Uani 1 1 d . . . H1A H 0.9794 0.1042 0.9536 0.080 Uiso 1 1 d . . . H1B H 1.1032 0.1423 0.8657 0.080 Uiso 1 1 d . . . H2A H 0.8551 0.2779 0.8467 0.080 Uiso 1 1 d . . . H3A H 0.8224 0.1911 0.6325 0.080 Uiso 1 1 d . . . H4A H 0.8579 -0.0566 0.5833 0.080 Uiso 1 1 d . . . H5A H 0.9466 -0.1122 0.7911 0.080 Uiso 1 1 d . . . H6A H 0.7202 -0.0818 0.8908 0.080 Uiso 1 1 d . . . H7A H 0.6170 -0.2369 0.6799 0.080 Uiso 1 1 d . . . H7B H 0.4889 -0.2302 0.7610 0.080 Uiso 1 1 d . . . H8A H 0.4772 -0.0949 0.5658 0.080 Uiso 1 1 d . . . H8B H 0.3264 -0.2060 0.5798 0.080 Uiso 1 1 d . . . H9A H 0.2481 0.0085 0.6356 0.080 Uiso 1 1 d . . . H9B H 0.3017 -0.0407 0.7576 0.080 Uiso 1 1 d . . . H10A H 0.5202 0.1488 0.6702 0.080 Uiso 1 1 d . . . H13A H 0.4047 0.2115 0.9821 0.080 Uiso 1 1 d . . . H13B H 0.5702 0.3337 0.9861 0.080 Uiso 1 1 d . . . H15A H 0.6963 0.5387 0.9205 0.080 Uiso 1 1 d . . . H16A H 0.9560 0.6373 0.8912 0.080 Uiso 1 1 d . . . H18A H 0.7638 0.4782 0.5317 0.080 Uiso 1 1 d . . . H19A H 0.4934 0.3708 0.5616 0.080 Uiso 1 1 d . . . H20A H 1.1152 0.7018 0.7457 0.080 Uiso 1 1 d . . . H20B H 1.1326 0.5561 0.6614 0.080 Uiso 1 1 d . . . H20C H 1.0459 0.6790 0.6255 0.080 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 0.0379(3) 0.0357(3) 0.0391(3) 0.0119(2) 0.0114(2) 0.0147(2) N1 0.0371(8) 0.0346(9) 0.0304(8) 0.0088(7) 0.0107(7) 0.0115(7) O1 0.0723(10) 0.0754(12) 0.0315(8) 0.0194(8) 0.0073(7) 0.0304(9) O2 0.0567(9) 0.0479(9) 0.0560(10) 0.0132(7) 0.0270(7) 0.0260(7) O3 0.0423(8) 0.0541(10) 0.0486(9) 0.0181(7) 0.0028(7) 0.0146(7) C1 0.0343(10) 0.0568(15) 0.0568(14) 0.0220(12) 0.0067(10) 0.0117(10) C2 0.0312(9) 0.0425(12) 0.0503(13) 0.0186(10) 0.0078(9) 0.0061(8) C3 0.0364(11) 0.0730(17) 0.0573(14) 0.0349(13) 0.0195(10) 0.0136(11) C4 0.0445(12) 0.0779(18) 0.0524(14) 0.0197(13) 0.0238(11) 0.0237(12) C5 0.0408(11) 0.0535(14) 0.0543(13) 0.0191(11) 0.0153(10) 0.0231(10) C6 0.0395(10) 0.0351(11) 0.0388(11) 0.0126(9) 0.0092(8) 0.0118(8) C7 0.0533(12) 0.0326(11) 0.0508(13) 0.0071(10) 0.0097(10) 0.0116(9) C8 0.0459(11) 0.0357(11) 0.0389(11) 0.0010(9) 0.0068(9) 0.0034(9) C9 0.0334(9) 0.0379(11) 0.0369(11) 0.0058(9) 0.0043(8) 0.0046(8) C10 0.0310(9) 0.0316(10) 0.0278(9) 0.0083(8) 0.0079(7) 0.0099(7) C11 0.0295(9) 0.0314(10) 0.0305(9) 0.0105(8) 0.0056(7) 0.0061(7) C12 0.0374(10) 0.0377(11) 0.0325(10) 0.0093(9) 0.0059(8) 0.0056(8) C13 0.0511(12) 0.0444(12) 0.0310(10) 0.0103(9) 0.0139(9) 0.0158(9) C14 0.0453(10) 0.0285(10) 0.0377(11) 0.0114(8) 0.0142(9) 0.0124(8) C15 0.0562(12) 0.0375(12) 0.0354(11) 0.0093(9) 0.0138(9) 0.0073(9) C16 0.0512(12) 0.0384(12) 0.0459(13) 0.0054(10) 0.0104(10) 0.0033(9) C17 0.0549(12) 0.0324(11) 0.0582(14) 0.0122(10) 0.0273(11) 0.0113(9) C18 0.0712(15) 0.0452(13) 0.0428(13) 0.0106(10) 0.0291(11) 0.0114(11) C19 0.0556(12) 0.0398(12) 0.0362(11) 0.0077(9) 0.0138(9) 0.0092(10) C20 0.0700(16) 0.0492(15) 0.091(2) 0.0112(14) 0.0466(15) 0.0057(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.4294(15) . ? S1 O2 1.4306(15) . ? S1 N1 1.6209(16) . ? S1 C14 1.765(2) . ? N1 C13 1.464(2) . ? N1 C10 1.495(2) . ? O1 C12 1.207(2) . ? C1 C5 1.531(3) . ? C1 C2 1.534(3) . ? C2 C3 1.512(3) . ? C2 C11 1.5655(16) . ? C3 C4 1.318(3) . ? C4 C5 1.509(3) . ? C5 C6 1.562(3) . ? C6 C7 1.540(3) . ? C6 C11 1.564(3) . ? C7 C8 1.517(3) . ? C8 C9 1.515(3) . ? C9 C10 1.517(3) . ? C10 C11 1.550(2) . ? C11 C12 1.522(3) . ? C12 C13 1.505(3) . ? C14 C19 1.388(3) . ? C14 C15 1.389(3) . ? C15 C16 1.380(3) . ? C16 C17 1.391(3) . ? C17 C18 1.383(3) . ? C17 C20 1.505(3) . ? C18 C19 1.384(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 O3 S1 O2 120.46(9) . . ? O3 S1 N1 107.42(9) . . ? O2 S1 N1 105.92(8) . . ? O3 S1 C14 106.75(9) . . ? O2 S1 C14 108.59(9) . . ? N1 S1 C14 107.03(8) . . ? C13 N1 C10 111.97(14) . . ? C13 N1 S1 120.94(13) . . ? C10 N1 S1 120.28(12) . . ? C5 C1 C2 93.05(16) . . ? C3 C2 C1 99.41(17) . . ? C3 C2 C11 106.55(16) . . ? C1 C2 C11 101.54(15) . . ? C4 C3 C2 107.7(2) . . ? C3 C4 C5 107.2(2) . . ? C4 C5 C1 100.5(2) . . ? C4 C5 C6 108.12(16) . . ? C1 C5 C6 100.25(16) . . ? C7 C6 C5 116.44(17) . . ? C7 C6 C11 117.25(15) . . ? C5 C6 C11 102.01(15) . . ? C8 C7 C6 115.16(17) . . ? C9 C8 C7 110.37(17) . . ? C8 C9 C10 109.21(15) . . ? N1 C10 C9 111.39(14) . . ? N1 C10 C11 104.80(14) . . ? C9 C10 C11 113.81(15) . . ? C12 C11 C10 102.84(14) . . ? C12 C11 C6 111.80(15) . . ? C10 C11 C6 118.06(15) . . ? C12 C11 C2 109.14(15) . . ? C10 C11 C2 112.78(14) . . ? C6 C11 C2 102.27(14) . . ? O1 C12 C13 123.10(18) . . ? O1 C12 C11 126.49(18) . . ? C13 C12 C11 110.41(16) . . ? N1 C13 C12 104.34(15) . . ? C19 C14 C15 120.04(18) . . ? C19 C14 S1 118.92(16) . . ? C15 C14 S1 120.93(15) . . ? C16 C15 C14 119.64(18) . . ? C15 C16 C17 121.3(2) . . ? C18 C17 C16 117.99(19) . . ? C18 C17 C20 120.4(2) . . ? C16 C17 C20 121.6(2) . . ? C17 C18 C19 121.82(19) . . ? C18 C19 C14 119.2(2) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.307 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.051 # Attachment 'DC09M.CIF-compound 36' data_dc09m _database_code_depnum_ccdc_archive 'CCDC 678652' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H21 N O3 S' _chemical_formula_weight 343.43 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 9.6137(6) _cell_length_b 12.3450(8) _cell_length_c 15.2962(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.7670(10) _cell_angle_gamma 90.00 _cell_volume 1738.19(19) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3815 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Equant _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.82682 _exptl_absorpt_correction_T_max 0.96161 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 10913 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0392 _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 -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.27 _reflns_number_total 4144 _reflns_number_gt 2942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0633P)^2^+0.6116P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4144 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1460 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.47030(6) 0.80528(5) 0.07363(4) 0.04676(18) Uani 1 1 d . . . O1 O 0.5132(2) 0.85834(15) 0.00200(12) 0.0617(5) Uani 1 1 d . . . O2 O 0.4800(2) 0.69042(14) 0.08358(13) 0.0626(5) Uani 1 1 d . . . O3 O 0.1056(2) 1.06753(14) 0.09090(14) 0.0689(5) Uani 1 1 d . . . N1 N 0.2995(2) 0.83616(15) 0.05747(12) 0.0449(4) Uani 1 1 d . . . C1 C 0.2513(3) 0.9471(2) 0.03109(17) 0.0547(6) Uani 1 1 d . . . C2 C 0.1661(2) 0.98137(18) 0.09568(16) 0.0469(5) Uani 1 1 d . . . C3 C 0.1685(2) 0.89126(17) 0.16373(15) 0.0422(5) Uani 1 1 d . . . C4 C 0.2223(2) 0.79307(18) 0.12171(15) 0.0427(5) Uani 1 1 d . . . C5 C 0.0830(3) 0.7325(2) 0.0716(2) 0.0631(7) Uani 1 1 d . . . C6 C -0.0130(3) 0.7452(2) 0.1351(2) 0.0749(9) Uani 1 1 d . . . C7 C 0.0160(3) 0.8601(2) 0.17330(19) 0.0588(7) Uani 1 1 d . . . C8 C 0.0363(3) 0.8811(3) 0.2767(2) 0.0829(10) Uani 1 1 d . . . C9 C 0.1446(4) 0.8010(3) 0.3306(2) 0.0874(10) Uani 1 1 d . . . C10 C 0.2726(3) 0.8276(3) 0.32264(18) 0.0722(9) Uani 1 1 d . . . C11 C 0.2534(3) 0.9276(2) 0.26372(17) 0.0572(6) Uani 1 1 d . . . C12 C 0.1289(4) 0.9829(3) 0.2906(2) 0.0813(10) Uani 1 1 d . . . C13 C 0.5696(2) 0.86202(18) 0.17873(15) 0.0410(5) Uani 1 1 d . . . C14 C 0.6084(2) 0.97085(18) 0.18458(15) 0.0452(5) Uani 1 1 d . . . C15 C 0.6754(2) 1.01558(19) 0.26852(16) 0.0472(5) Uani 1 1 d . . . C16 C 0.7063(2) 0.9540(2) 0.34838(16) 0.0474(5) Uani 1 1 d . . . C17 C 0.6707(3) 0.8446(2) 0.34050(16) 0.0522(6) Uani 1 1 d . . . C18 C 0.6027(2) 0.79825(18) 0.25710(16) 0.0482(5) Uani 1 1 d . . . C19 C 0.7758(3) 1.0042(2) 0.43967(19) 0.0713(8) Uani 1 1 d . . . H1A H 0.3344 0.9988 0.0371 0.080 Uiso 1 1 d . . . H1B H 0.1795 0.9445 -0.0318 0.080 Uiso 1 1 d . . . H4A H 0.2905 0.7497 0.1677 0.080 Uiso 1 1 d . . . H5A H 0.0352 0.7747 0.0087 0.080 Uiso 1 1 d . . . H5B H 0.1051 0.6584 0.0639 0.080 Uiso 1 1 d . . . H6A H -0.1153 0.7336 0.0995 0.080 Uiso 1 1 d . . . H6B H 0.0199 0.6966 0.1811 0.080 Uiso 1 1 d . . . H7A H -0.0564 0.9078 0.1380 0.080 Uiso 1 1 d . . . H8A H -0.0494 0.8886 0.2911 0.080 Uiso 1 1 d . . . H9A H 0.1190 0.7419 0.3547 0.080 Uiso 1 1 d . . . H10A H 0.3561 0.7902 0.3456 0.080 Uiso 1 1 d . . . H11A H 0.3385 0.9666 0.2664 0.080 Uiso 1 1 d . . . H12A H 0.0862 1.0396 0.2501 0.080 Uiso 1 1 d . . . H12B H 0.1641 1.0081 0.3503 0.080 Uiso 1 1 d . . . H14A H 0.5946 1.0139 0.1317 0.080 Uiso 1 1 d . . . H15A H 0.7047 1.0898 0.2727 0.080 Uiso 1 1 d . . . H17A H 0.6934 0.8010 0.3951 0.080 Uiso 1 1 d . . . H18A H 0.5785 0.7251 0.2514 0.080 Uiso 1 1 d . . . H19A H 0.8238 1.0703 0.4354 0.080 Uiso 1 1 d . . . H19B H 0.8358 0.9596 0.4716 0.080 Uiso 1 1 d . . . H19C H 0.6954 1.0248 0.4644 0.080 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 0.0528(3) 0.0481(3) 0.0454(3) -0.0023(3) 0.0237(3) 0.0031(3) O1 0.0734(12) 0.0725(12) 0.0508(10) 0.0015(9) 0.0366(9) -0.0027(9) O2 0.0740(12) 0.0479(10) 0.0725(12) -0.0099(9) 0.0318(10) 0.0051(8) O3 0.0817(13) 0.0446(10) 0.0753(13) 0.0062(9) 0.0143(10) 0.0135(9) N1 0.0488(10) 0.0487(11) 0.0390(10) 0.0033(8) 0.0155(8) 0.0006(8) C1 0.0487(13) 0.0611(15) 0.0542(14) 0.0204(12) 0.0146(11) 0.0068(11) C2 0.0450(12) 0.0421(13) 0.0471(12) 0.0014(10) 0.0029(10) -0.0027(10) C3 0.0420(11) 0.0430(12) 0.0420(12) 0.0025(9) 0.0127(9) 0.0025(9) C4 0.0450(11) 0.0410(12) 0.0446(12) 0.0025(9) 0.0168(9) -0.0013(9) C5 0.0625(16) 0.0501(15) 0.0774(19) -0.0092(13) 0.0210(14) -0.0138(12) C6 0.0547(16) 0.0692(19) 0.105(2) 0.0069(17) 0.0304(16) -0.0141(14) C7 0.0457(13) 0.0652(17) 0.0698(17) 0.0090(13) 0.0233(12) 0.0078(12) C8 0.0692(19) 0.117(3) 0.081(2) 0.0163(19) 0.0506(17) 0.0256(19) C9 0.099(2) 0.110(3) 0.071(2) 0.0319(19) 0.0527(19) 0.024(2) C10 0.0746(19) 0.103(2) 0.0426(14) 0.0157(15) 0.0231(13) 0.0273(17) C11 0.0594(15) 0.0701(17) 0.0425(13) -0.0055(12) 0.0155(11) 0.0065(13) C12 0.095(2) 0.095(2) 0.0576(17) -0.0117(16) 0.0282(17) 0.0287(19) C13 0.0377(10) 0.0439(12) 0.0444(12) 0.0050(9) 0.0165(9) 0.0061(9) C14 0.0476(12) 0.0460(13) 0.0459(12) 0.0112(10) 0.0196(10) 0.0038(10) C15 0.0452(12) 0.0458(13) 0.0522(13) 0.0054(10) 0.0166(10) -0.0020(10) C16 0.0371(11) 0.0575(14) 0.0462(13) 0.0065(10) 0.0095(9) 0.0000(10) C17 0.0479(13) 0.0568(14) 0.0495(13) 0.0178(11) 0.0102(11) 0.0029(11) C18 0.0466(12) 0.0421(12) 0.0570(14) 0.0112(11) 0.0167(11) 0.0029(10) C19 0.0732(19) 0.0730(19) 0.0565(16) 0.0066(14) 0.0009(14) -0.0093(15) _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 O2 1.4263(18) . ? S1 O1 1.4351(17) . ? S1 N1 1.6336(19) . ? S1 C13 1.761(2) . ? O3 C2 1.204(3) . ? N1 C1 1.465(3) . ? N1 C4 1.490(3) . ? C1 C2 1.514(3) . ? C2 C3 1.519(3) . ? C3 C4 1.530(3) . ? C3 C7 1.562(3) . ? C3 C11 1.577(3) . ? C4 C5 1.532(3) . ? C5 C6 1.529(4) . ? C6 C7 1.529(4) . ? C7 C8 1.559(4) . ? C8 C9 1.498(5) . ? C8 C12 1.520(5) . ? C9 C10 1.313(4) . ? C10 C11 1.508(4) . ? C11 C12 1.534(4) . ? C13 C14 1.390(3) . ? C13 C18 1.392(3) . ? C14 C15 1.375(3) . ? C15 C16 1.396(3) . ? C16 C17 1.390(3) . ? C16 C19 1.498(4) . ? C17 C18 1.379(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 O2 S1 O1 120.72(11) . . ? O2 S1 N1 106.28(11) . . ? O1 S1 N1 105.99(10) . . ? O2 S1 C13 107.23(11) . . ? O1 S1 C13 108.41(11) . . ? N1 S1 C13 107.58(10) . . ? C1 N1 C4 109.72(17) . . ? C1 N1 S1 118.95(15) . . ? C4 N1 S1 119.15(14) . . ? N1 C1 C2 105.60(18) . . ? O3 C2 C1 123.3(2) . . ? O3 C2 C3 126.9(2) . . ? C1 C2 C3 109.79(19) . . ? C2 C3 C4 103.44(17) . . ? C2 C3 C7 114.55(19) . . ? C4 C3 C7 106.50(18) . . ? C2 C3 C11 110.96(19) . . ? C4 C3 C11 119.30(18) . . ? C7 C3 C11 102.49(19) . . ? N1 C4 C3 106.69(17) . . ? N1 C4 C5 111.95(19) . . ? C3 C4 C5 104.15(19) . . ? C6 C5 C4 103.4(2) . . ? C5 C6 C7 105.1(2) . . ? C6 C7 C8 119.9(3) . . ? C6 C7 C3 105.4(2) . . ? C8 C7 C3 102.0(2) . . ? C9 C8 C12 100.5(3) . . ? C9 C8 C7 108.1(2) . . ? C12 C8 C7 100.1(2) . . ? C10 C9 C8 107.8(3) . . ? C9 C10 C11 107.7(3) . . ? C10 C11 C12 100.1(2) . . ? C10 C11 C3 106.7(2) . . ? C12 C11 C3 99.3(2) . . ? C8 C12 C11 93.7(2) . . ? C14 C13 C18 120.0(2) . . ? C14 C13 S1 120.52(17) . . ? C18 C13 S1 119.35(18) . . ? C15 C14 C13 119.5(2) . . ? C14 C15 C16 121.5(2) . . ? C17 C16 C15 117.9(2) . . ? C17 C16 C19 121.1(2) . . ? C15 C16 C19 121.0(2) . . ? C18 C17 C16 121.5(2) . . ? C17 C18 C13 119.5(2) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.349 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.043 # Attachment 'FB10MCIF-compound 22.cif' data_fb10m _database_code_depnum_ccdc_archive 'CCDC 678653' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H21 N O4 S' _chemical_formula_weight 359.43 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 Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 16.537(3) _cell_length_b 12.716(2) _cell_length_c 16.984(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3571.5(10) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1013 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Equant _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.74399 _exptl_absorpt_correction_T_max 0.94430 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 21209 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 28.30 _reflns_number_total 7620 _reflns_number_gt 4067 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.2000P)^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 0.44(17) _refine_ls_number_reflns 7620 _refine_ls_number_parameters 450 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1826 _refine_ls_R_factor_gt 0.1268 _refine_ls_wR_factor_ref 0.3135 _refine_ls_wR_factor_gt 0.2733 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.003 _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 0.29603(10) 0.49502(13) 0.4218 0.0490(4) Uani 1 1 d . . . S2 S -0.05540(11) -0.02816(15) -0.08492(14) 0.0577(5) Uani 1 1 d . . . O1 O 0.3717(3) 0.5469(4) 0.4273(4) 0.0765(18) Uani 1 1 d . . . O2 O 0.2479(4) 0.4808(5) 0.4914(3) 0.0730(16) Uani 1 1 d . . . O3 O 0.0510(3) 0.5697(5) 0.2640(4) 0.0754(18) Uani 1 1 d . . . O4 O 0.0667(4) 0.8643(4) 0.1168(6) 0.100(2) Uani 1 1 d . . . O5 O -0.0087(4) -0.0528(5) -0.1538(3) 0.084(2) Uani 1 1 d . . . O6 O -0.1304(3) 0.0190(4) -0.0931(4) 0.0698(16) Uani 1 1 d . . . O7 O 0.1896(3) 0.0602(5) 0.0685(4) 0.0765(18) Uani 1 1 d . . . O8 O 0.1697(5) 0.3667(5) 0.2099(5) 0.093(2) Uani 1 1 d . . . N1 N 0.2385(3) 0.5598(4) 0.3619(3) 0.0467(13) Uani 1 1 d . . . N2 N 0.0024(3) 0.0441(4) -0.0297(3) 0.0441(13) Uani 1 1 d . . . C1 C 0.1525(4) 0.5202(6) 0.3578(5) 0.0505(17) Uani 1 1 d . . . H1B H 0.1509 0.4444 0.3512 0.061 Uiso 1 1 calc R . . H1C H 0.1224 0.5391 0.4047 0.061 Uiso 1 1 calc R . . C2 C 0.1196(4) 0.5756(6) 0.2862(5) 0.0494(16) Uani 1 1 d . . . C3 C 0.1874(4) 0.6397(5) 0.2453(5) 0.0431(15) Uani 1 1 d . . . C4 C 0.1818(5) 0.6375(6) 0.1608(5) 0.0549(18) Uani 1 1 d . . . H4A H 0.2065 0.5819 0.1345 0.066 Uiso 1 1 calc R . . C5 C 0.1433(5) 0.7102(6) 0.1171(6) 0.068(2) Uani 1 1 d . . . H5A H 0.1414 0.7039 0.0625 0.082 Uiso 1 1 calc R . . C6 C 0.1038(5) 0.8010(6) 0.1571(6) 0.064(2) Uani 1 1 d . . . C7 C 0.1079(5) 0.8074(6) 0.2433(6) 0.065(2) Uani 1 1 d . . . H7A H 0.0587 0.7772 0.2648 0.078 Uiso 1 1 calc R . . H7B H 0.1092 0.8809 0.2583 0.078 Uiso 1 1 calc R . . C8 C 0.1800(5) 0.7522(5) 0.2811(5) 0.0535(17) Uani 1 1 d . . . H8A H 0.1693 0.7452 0.3376 0.064 Uiso 1 1 calc R . . C9 C 0.2577(5) 0.8143(6) 0.2709(6) 0.067(2) Uani 1 1 d . . . H9A H 0.2667 0.8272 0.2153 0.080 Uiso 1 1 calc R . . H9B H 0.2521 0.8820 0.2967 0.080 Uiso 1 1 calc R . . C10 C 0.3304(6) 0.7573(7) 0.3048(6) 0.081(3) Uani 1 1 d . . . H10A H 0.3788 0.7982 0.2943 0.097 Uiso 1 1 calc R . . H10B H 0.3242 0.7518 0.3614 0.097 Uiso 1 1 calc R . . C11 C 0.3408(4) 0.6489(6) 0.2708(6) 0.068(2) Uani 1 1 d . . . H11A H 0.3848 0.6135 0.2977 0.081 Uiso 1 1 calc R . . H11B H 0.3552 0.6546 0.2155 0.081 Uiso 1 1 calc R . . C12 C 0.2636(4) 0.5831(5) 0.2787(4) 0.0424(15) Uani 1 1 d . . . H12A H 0.2711 0.5165 0.2506 0.051 Uiso 1 1 calc R . . C13 C 0.3130(4) 0.3709(5) 0.3778(4) 0.0482(17) Uani 1 1 d . . . C14 C 0.3748(4) 0.3587(6) 0.3247(5) 0.0547(19) Uani 1 1 d . . . H14A H 0.4107 0.4137 0.3156 0.066 Uiso 1 1 calc R . . C15 C 0.3837(5) 0.2649(6) 0.2846(6) 0.063(2) Uani 1 1 d . . . H15A H 0.4252 0.2582 0.2480 0.076 Uiso 1 1 calc R . . C16 C 0.3333(5) 0.1822(6) 0.2973(5) 0.062(2) Uani 1 1 d . . . C17 C 0.2722(5) 0.1938(6) 0.3509(6) 0.067(2) Uani 1 1 d . . . H17A H 0.2375 0.1377 0.3604 0.080 Uiso 1 1 calc R . . C18 C 0.2606(4) 0.2882(6) 0.3918(5) 0.0554(18) Uani 1 1 d . . . H18A H 0.2184 0.2951 0.4277 0.066 Uiso 1 1 calc R . . C19 C 0.3439(7) 0.0813(6) 0.2487(6) 0.084(3) Uani 1 1 d . . . H19A H 0.3896 0.0889 0.2143 0.126 Uiso 1 1 calc R . . H19B H 0.2961 0.0691 0.2180 0.126 Uiso 1 1 calc R . . H19C H 0.3526 0.0229 0.2835 0.126 Uiso 1 1 calc R . . C20 C 0.0884(4) 0.0076(5) -0.0262(4) 0.0426(15) Uani 1 1 d . . . H20A H 0.1176 0.0267 -0.0735 0.051 Uiso 1 1 calc R . . H20B H 0.0915 -0.0679 -0.0188 0.051 Uiso 1 1 calc R . . C21 C 0.1210(4) 0.0664(5) 0.0455(5) 0.0484(17) Uani 1 1 d . . . C22 C 0.0544(4) 0.1337(5) 0.0822(4) 0.0407(14) Uani 1 1 d . . . C23 C 0.0580(4) 0.1377(5) 0.1695(4) 0.0501(17) Uani 1 1 d . . . H23A H 0.0327 0.0837 0.1970 0.060 Uiso 1 1 calc R . . C24 C 0.0937(5) 0.2109(6) 0.2108(5) 0.0573(19) Uani 1 1 d . . . H24A H 0.0938 0.2065 0.2655 0.069 Uiso 1 1 calc R . . C25 C 0.1340(5) 0.3006(6) 0.1718(5) 0.066(2) Uani 1 1 d . . . C26 C 0.1340(5) 0.3013(6) 0.0840(5) 0.064(2) Uani 1 1 d . . . H26A H 0.1843 0.2703 0.0660 0.076 Uiso 1 1 calc R . . H26B H 0.1334 0.3739 0.0665 0.076 Uiso 1 1 calc R . . C27 C 0.0645(5) 0.2439(6) 0.0444(5) 0.0546(18) Uani 1 1 d . . . H27A H 0.0781 0.2344 -0.0113 0.066 Uiso 1 1 calc R . . C28 C -0.0121(6) 0.3090(6) 0.0493(6) 0.070(2) Uani 1 1 d . . . H28A H -0.0042 0.3737 0.0201 0.084 Uiso 1 1 calc R . . H28B H -0.0217 0.3276 0.1039 0.084 Uiso 1 1 calc R . . C29 C -0.0872(8) 0.2523(8) 0.0170(8) 0.102(4) Uani 1 1 d . . . H29A H -0.1347 0.2950 0.0267 0.122 Uiso 1 1 calc R . . H29B H -0.0817 0.2437 -0.0395 0.122 Uiso 1 1 calc R . . C30 C -0.0982(5) 0.1464(6) 0.0546(6) 0.067(2) Uani 1 1 d . . . H30A H -0.1421 0.1101 0.0283 0.081 Uiso 1 1 calc R . . H30B H -0.1138 0.1563 0.1091 0.081 Uiso 1 1 calc R . . C31 C -0.0231(4) 0.0769(5) 0.0519(4) 0.0420(14) Uani 1 1 d . . . H31A H -0.0325 0.0139 0.0838 0.050 Uiso 1 1 calc R . . C32 C -0.0707(4) -0.1486(5) -0.0343(4) 0.0479(17) Uani 1 1 d . . . C33 C -0.1281(4) -0.1507(5) 0.0268(4) 0.0467(16) Uani 1 1 d . . . H33A H -0.1597 -0.0921 0.0377 0.056 Uiso 1 1 calc R . . C34 C -0.1364(4) -0.2421(5) 0.0704(4) 0.0478(16) Uani 1 1 d . . . H34A H -0.1748 -0.2444 0.1104 0.057 Uiso 1 1 calc R . . C35 C -0.0890(4) -0.3308(6) 0.0562(5) 0.0543(18) Uani 1 1 d . . . C36 C -0.0330(5) -0.3234(6) -0.0046(6) 0.063(2) Uani 1 1 d . . . H36A H -0.0003 -0.3811 -0.0155 0.076 Uiso 1 1 calc R . . C37 C -0.0241(4) -0.2348(7) -0.0488(5) 0.059(2) Uani 1 1 d . . . H37A H 0.0139 -0.2332 -0.0892 0.071 Uiso 1 1 calc R . . C38 C -0.0992(6) -0.4276(6) 0.1048(6) 0.081(3) Uani 1 1 d . . . H38A H -0.1417 -0.4168 0.1424 0.121 Uiso 1 1 calc R . . H38B H -0.0496 -0.4425 0.1320 0.121 Uiso 1 1 calc R . . H38C H -0.1127 -0.4857 0.0713 0.121 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 0.0538(9) 0.0625(9) 0.0306(8) 0.0023(8) -0.0131(8) 0.0014(8) S2 0.0613(11) 0.0804(12) 0.0315(9) 0.0002(10) -0.0101(8) -0.0117(9) O1 0.071(4) 0.082(4) 0.076(5) 0.002(4) -0.037(4) -0.021(3) O2 0.083(4) 0.108(4) 0.028(3) 0.003(3) -0.007(3) 0.002(3) O3 0.043(3) 0.102(4) 0.081(5) 0.021(4) -0.006(3) -0.002(3) O4 0.109(5) 0.056(3) 0.136(7) 0.017(4) -0.037(5) 0.017(4) O5 0.100(5) 0.121(5) 0.031(3) -0.015(3) 0.009(3) -0.039(4) O6 0.060(3) 0.097(4) 0.053(4) 0.010(3) -0.031(3) -0.012(3) O7 0.044(3) 0.101(5) 0.084(5) -0.022(4) -0.006(3) -0.003(3) O8 0.118(6) 0.076(4) 0.084(5) -0.021(4) -0.014(4) -0.038(4) N1 0.051(3) 0.055(3) 0.034(3) 0.003(2) -0.004(2) -0.003(3) N2 0.047(3) 0.054(3) 0.031(3) 0.003(2) 0.003(2) -0.007(3) C1 0.039(4) 0.073(4) 0.040(4) -0.001(3) 0.003(3) -0.004(3) C2 0.045(4) 0.063(4) 0.040(4) -0.001(3) 0.001(3) -0.005(3) C3 0.039(3) 0.043(3) 0.047(4) 0.001(3) 0.005(3) 0.002(3) C4 0.050(4) 0.072(5) 0.042(4) -0.004(4) 0.001(3) -0.001(4) C5 0.073(5) 0.066(5) 0.066(6) 0.014(4) -0.010(4) 0.005(4) C6 0.060(5) 0.065(5) 0.067(6) 0.010(4) -0.022(4) -0.007(4) C7 0.059(5) 0.054(4) 0.083(6) 0.004(4) 0.001(4) 0.017(4) C8 0.064(4) 0.053(4) 0.044(4) -0.009(3) 0.007(3) -0.004(3) C9 0.089(6) 0.047(4) 0.065(5) -0.002(4) -0.007(5) -0.010(4) C10 0.077(6) 0.087(6) 0.078(7) 0.018(5) -0.028(5) -0.040(5) C11 0.049(4) 0.071(5) 0.083(6) 0.029(5) 0.002(4) -0.010(4) C12 0.040(3) 0.048(4) 0.040(3) 0.003(3) 0.004(3) 0.000(3) C13 0.044(4) 0.057(4) 0.044(4) 0.015(3) -0.007(3) -0.004(3) C14 0.049(4) 0.049(4) 0.066(5) 0.020(4) -0.001(3) 0.002(3) C15 0.063(5) 0.060(5) 0.066(5) 0.018(4) 0.006(4) 0.002(4) C16 0.060(5) 0.063(5) 0.063(5) 0.024(4) -0.002(4) -0.005(4) C17 0.067(5) 0.063(5) 0.070(6) 0.022(4) -0.012(4) -0.016(4) C18 0.051(4) 0.063(4) 0.052(4) 0.022(3) 0.003(3) -0.008(3) C19 0.114(8) 0.053(5) 0.085(7) 0.017(5) 0.004(6) 0.004(5) C20 0.043(4) 0.048(4) 0.036(4) -0.001(3) 0.005(3) -0.002(3) C21 0.049(4) 0.049(4) 0.047(4) 0.002(3) 0.000(3) -0.012(3) C22 0.045(4) 0.046(3) 0.031(3) 0.000(2) -0.001(3) -0.010(3) C23 0.063(5) 0.050(4) 0.038(4) 0.007(3) -0.001(3) -0.006(3) C24 0.070(5) 0.064(4) 0.038(4) 0.001(3) -0.002(3) -0.016(4) C25 0.085(6) 0.058(4) 0.055(5) -0.005(4) -0.005(4) -0.019(4) C26 0.081(6) 0.052(4) 0.057(5) -0.002(4) 0.007(4) -0.027(4) C27 0.080(5) 0.053(4) 0.031(3) 0.007(3) -0.004(3) -0.021(4) C28 0.095(6) 0.049(4) 0.067(5) -0.001(4) -0.012(5) 0.001(4) C29 0.131(10) 0.070(6) 0.103(8) -0.001(6) -0.043(7) 0.043(6) C30 0.064(5) 0.054(4) 0.084(6) -0.013(4) 0.007(4) 0.010(4) C31 0.041(3) 0.049(4) 0.036(3) -0.004(3) 0.002(3) 0.000(3) C32 0.045(4) 0.060(4) 0.039(4) -0.014(3) -0.008(3) -0.010(3) C33 0.043(4) 0.054(4) 0.044(4) -0.009(3) 0.005(3) -0.001(3) C34 0.047(4) 0.049(4) 0.047(4) -0.006(3) 0.004(3) -0.006(3) C35 0.050(4) 0.048(4) 0.065(5) -0.004(3) -0.008(4) 0.002(3) C36 0.058(5) 0.046(4) 0.086(6) -0.007(4) 0.010(4) 0.006(3) C37 0.046(4) 0.077(5) 0.055(5) -0.023(4) 0.003(3) -0.006(4) C38 0.110(7) 0.054(5) 0.079(7) 0.004(5) -0.009(6) -0.008(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 O1 1.417(5) . ? S1 O2 1.436(6) . ? S1 N1 1.619(6) . ? S1 C13 1.769(7) . ? S2 O6 1.384(6) . ? S2 O5 1.437(6) . ? S2 N2 1.624(6) . ? S2 C32 1.775(7) . ? O3 C2 1.197(8) . ? O4 C6 1.221(10) . ? O7 C21 1.202(9) . ? O8 C25 1.215(10) . ? N1 C12 1.501(8) . ? N1 C1 1.510(9) . ? N2 C20 1.497(9) . ? N2 C31 1.507(8) . ? C1 C2 1.507(10) . ? C2 C3 1.552(10) . ? C3 C4 1.438(10) . ? C3 C12 1.558(9) . ? C3 C8 1.560(9) . ? C4 C5 1.346(11) . ? C5 C6 1.490(12) . ? C6 C7 1.469(12) . ? C7 C8 1.525(11) . ? C8 C9 1.518(10) . ? C9 C10 1.517(12) . ? C10 C11 1.505(13) . ? C11 C12 1.533(9) . ? C13 C14 1.372(10) . ? C13 C18 1.384(9) . ? C14 C15 1.381(11) . ? C15 C16 1.359(10) . ? C16 C17 1.369(12) . ? C16 C19 1.535(12) . ? C17 C18 1.399(11) . ? C20 C21 1.527(10) . ? C21 C22 1.527(10) . ? C22 C23 1.485(9) . ? C22 C27 1.550(9) . ? C22 C31 1.558(9) . ? C23 C24 1.307(10) . ? C24 C25 1.477(11) . ? C25 C26 1.490(12) . ? C26 C27 1.520(11) . ? C27 C28 1.515(12) . ? C28 C29 1.538(14) . ? C29 C30 1.502(13) . ? C30 C31 1.524(10) . ? C32 C37 1.363(10) . ? C32 C33 1.405(10) . ? C33 C34 1.385(10) . ? C34 C35 1.395(10) . ? C35 C36 1.391(12) . ? C35 C38 1.491(11) . ? C36 C37 1.361(12) . ? 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 O1 S1 O2 119.6(4) . . ? O1 S1 N1 108.9(3) . . ? O2 S1 N1 104.8(3) . . ? O1 S1 C13 107.6(4) . . ? O2 S1 C13 108.8(4) . . ? N1 S1 C13 106.3(3) . . ? O6 S2 O5 119.6(4) . . ? O6 S2 N2 109.9(3) . . ? O5 S2 N2 106.1(3) . . ? O6 S2 C32 107.1(3) . . ? O5 S2 C32 106.5(4) . . ? N2 S2 C32 107.0(3) . . ? C12 N1 C1 106.5(5) . . ? C12 N1 S1 121.9(4) . . ? C1 N1 S1 114.4(4) . . ? C20 N2 C31 108.3(5) . . ? C20 N2 S2 114.0(4) . . ? C31 N2 S2 121.5(4) . . ? C2 C1 N1 102.8(5) . . ? O3 C2 C1 124.6(7) . . ? O3 C2 C3 125.2(7) . . ? C1 C2 C3 110.3(6) . . ? C4 C3 C2 113.0(6) . . ? C4 C3 C12 114.0(6) . . ? C2 C3 C12 100.3(5) . . ? C4 C3 C8 113.7(6) . . ? C2 C3 C8 104.5(5) . . ? C12 C3 C8 110.2(6) . . ? C5 C4 C3 124.6(8) . . ? C4 C5 C6 119.2(8) . . ? O4 C6 C7 123.0(9) . . ? O4 C6 C5 118.4(9) . . ? C7 C6 C5 118.5(7) . . ? C6 C7 C8 115.5(7) . . ? C9 C8 C7 112.0(6) . . ? C9 C8 C3 111.5(6) . . ? C7 C8 C3 108.6(6) . . ? C10 C9 C8 112.2(6) . . ? C11 C10 C9 112.5(7) . . ? C10 C11 C12 111.8(7) . . ? N1 C12 C11 115.0(6) . . ? N1 C12 C3 102.2(5) . . ? C11 C12 C3 112.9(5) . . ? C14 C13 C18 119.6(7) . . ? C14 C13 S1 119.8(5) . . ? C18 C13 S1 120.4(6) . . ? C13 C14 C15 120.1(7) . . ? C16 C15 C14 121.7(8) . . ? C15 C16 C17 118.3(8) . . ? C15 C16 C19 119.4(8) . . ? C17 C16 C19 122.2(7) . . ? C16 C17 C18 121.6(7) . . ? C13 C18 C17 118.7(7) . . ? N2 C20 C21 102.5(5) . . ? O7 C21 C22 125.8(7) . . ? O7 C21 C20 124.0(7) . . ? C22 C21 C20 110.2(6) . . ? C23 C22 C21 113.4(6) . . ? C23 C22 C27 112.2(6) . . ? C21 C22 C27 105.1(5) . . ? C23 C22 C31 112.2(5) . . ? C21 C22 C31 101.5(5) . . ? C27 C22 C31 111.7(5) . . ? C24 C23 C22 125.4(7) . . ? C23 C24 C25 120.8(8) . . ? O8 C25 C24 120.9(9) . . ? O8 C25 C26 122.0(8) . . ? C24 C25 C26 117.0(7) . . ? C25 C26 C27 116.1(7) . . ? C28 C27 C26 110.2(7) . . ? C28 C27 C22 112.4(6) . . ? C26 C27 C22 109.4(6) . . ? C27 C28 C29 113.5(7) . . ? C30 C29 C28 111.5(8) . . ? C29 C30 C31 114.1(8) . . ? N2 C31 C30 114.5(6) . . ? N2 C31 C22 101.7(5) . . ? C30 C31 C22 113.1(5) . . ? C37 C32 C33 120.0(7) . . ? C37 C32 S2 121.7(6) . . ? C33 C32 S2 118.1(5) . . ? C34 C33 C32 118.5(6) . . ? C33 C34 C35 122.0(7) . . ? C36 C35 C34 116.6(7) . . ? C36 C35 C38 122.9(7) . . ? C34 C35 C38 120.6(8) . . ? C37 C36 C35 122.5(7) . . ? C36 C37 C32 120.3(7) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 2.293 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.172