# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email tooi@apchem.nagoya-u.ac.jp _publ_contact_author_name 'Takashi Ooi' loop_ _publ_author_name 'Kohsuke Ohmatsu' 'Ayano Goto' 'Takashi Ooi' data_1121ago _database_code_depnum_ccdc_archive 'CCDC 867728' #TrackingRef '- 4a major.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 N2 O4 S' _chemical_formula_weight 400.48 _chemical_absolute_configuration S,S 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.817(2) _cell_length_b 10.8098(16) _cell_length_c 14.445(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.403(3) _cell_angle_gamma 90.00 _cell_volume 2128.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5750 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.24 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9315 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15602 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 28.30 _reflns_number_total 8724 _reflns_number_gt 7844 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.8983P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(7) _refine_ls_number_reflns 8724 _refine_ls_number_parameters 513 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1345 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.002 _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 C1 C 0.3993(2) 0.0227(3) 0.84508(19) 0.0196(6) Uani 1 1 d . . . H1 H 0.4459 0.0411 0.9040 0.023 Uiso 1 1 calc R . . C2 C 0.3187(2) -0.0575(3) 0.8728(2) 0.0205(6) Uani 1 1 d . . . C3 C 0.3361(2) -0.1230(3) 0.9567(2) 0.0279(7) Uani 1 1 d . . . H3 H 0.3984 -0.1177 0.9956 0.033 Uiso 1 1 calc R . . C4 C 0.2633(3) -0.1961(4) 0.9841(2) 0.0330(8) Uani 1 1 d . . . H4 H 0.2761 -0.2407 1.0415 0.040 Uiso 1 1 calc R . . C5 C 0.1724(2) -0.2043(3) 0.9285(2) 0.0313(7) Uani 1 1 d . . . H5 H 0.1226 -0.2542 0.9476 0.038 Uiso 1 1 calc R . . C6 C 0.1539(2) -0.1402(3) 0.8454(3) 0.0326(8) Uani 1 1 d . . . H6 H 0.0912 -0.1457 0.8072 0.039 Uiso 1 1 calc R . . C7 C 0.2267(2) -0.0670(3) 0.8168(2) 0.0290(7) Uani 1 1 d . . . H7 H 0.2136 -0.0235 0.7590 0.035 Uiso 1 1 calc R . . C8 C 0.45925(19) -0.0448(3) 0.7779(2) 0.0210(6) Uani 1 1 d . . . C9 C 0.4868(3) -0.1779(3) 0.8103(3) 0.0333(8) Uani 1 1 d . . . H9A H 0.4270 -0.2270 0.8088 0.050 Uiso 1 1 calc R . . H9B H 0.5233 -0.1762 0.8744 0.050 Uiso 1 1 calc R . . H9C H 0.5277 -0.2150 0.7683 0.050 Uiso 1 1 calc R . . C10 C 0.4083(2) -0.0469(3) 0.6807(2) 0.0253(7) Uani 1 1 d . . . C11 C 0.5634(2) 0.1790(3) 0.7244(2) 0.0258(7) Uani 1 1 d . . . C12 C 0.5606(2) 0.2828(3) 0.7797(3) 0.0352(8) Uani 1 1 d . . . H12 H 0.5577 0.2756 0.8448 0.042 Uiso 1 1 calc R . . C13 C 0.5622(3) 0.3975(4) 0.7375(5) 0.0595(15) Uani 1 1 d . . . H13 H 0.5607 0.4704 0.7739 0.071 Uiso 1 1 calc R . . C14 C 0.5659(3) 0.4064(5) 0.6432(5) 0.0695(18) Uani 1 1 d . . . H14 H 0.5678 0.4857 0.6152 0.083 Uiso 1 1 calc R . . C15 C 0.5670(3) 0.3029(6) 0.5895(4) 0.0607(15) Uani 1 1 d . . . H15 H 0.5688 0.3105 0.5243 0.073 Uiso 1 1 calc R . . C16 C 0.5654(3) 0.1874(4) 0.6294(2) 0.0403(9) Uani 1 1 d . . . H16 H 0.5657 0.1149 0.5922 0.048 Uiso 1 1 calc R . . C17 C 0.3548(2) 0.2361(3) 0.8663(2) 0.0236(6) Uani 1 1 d . . . C18 C 0.2773(2) 0.4399(3) 0.8688(2) 0.0286(7) Uani 1 1 d . . . C19 C 0.2292(3) 0.4128(4) 0.9531(3) 0.0351(8) Uani 1 1 d . . . H19A H 0.1730 0.3576 0.9348 0.053 Uiso 1 1 calc R . . H19B H 0.2066 0.4903 0.9777 0.053 Uiso 1 1 calc R . . H19C H 0.2767 0.3727 1.0018 0.053 Uiso 1 1 calc R . . C20 C 0.2059(3) 0.5044(4) 0.7932(3) 0.0470(11) Uani 1 1 d . . . H20A H 0.2381 0.5209 0.7389 0.071 Uiso 1 1 calc R . . H20B H 0.1849 0.5827 0.8178 0.071 Uiso 1 1 calc R . . H20C H 0.1486 0.4513 0.7742 0.071 Uiso 1 1 calc R . . C21 C 0.3719(3) 0.5119(3) 0.8923(3) 0.0403(9) Uani 1 1 d . . . H21A H 0.4173 0.4670 0.9399 0.061 Uiso 1 1 calc R . . H21B H 0.3581 0.5935 0.9167 0.061 Uiso 1 1 calc R . . H21C H 0.4015 0.5220 0.8356 0.061 Uiso 1 1 calc R . . C22 C 0.1480(2) 0.2628(3) 0.33469(19) 0.0229(6) Uani 1 1 d . . . H22 H 0.0788 0.2648 0.3469 0.027 Uiso 1 1 calc R . . C23 C 0.1466(2) 0.1949(3) 0.2415(2) 0.0254(6) Uani 1 1 d . . . C24 C 0.0623(3) 0.1326(3) 0.2013(2) 0.0343(8) Uani 1 1 d . . . H24 H 0.0070 0.1299 0.2327 0.041 Uiso 1 1 calc R . . C25 C 0.0587(3) 0.0741(4) 0.1148(3) 0.0451(10) Uani 1 1 d . . . H25 H 0.0009 0.0319 0.0871 0.054 Uiso 1 1 calc R . . C26 C 0.1387(4) 0.0771(4) 0.0694(2) 0.0484(11) Uani 1 1 d . . . H26 H 0.1360 0.0374 0.0103 0.058 Uiso 1 1 calc R . . C27 C 0.2227(3) 0.1378(4) 0.1093(3) 0.0447(10) Uani 1 1 d . . . H27 H 0.2782 0.1389 0.0783 0.054 Uiso 1 1 calc R . . C28 C 0.2265(3) 0.1975(4) 0.1950(2) 0.0360(8) Uani 1 1 d . . . H28 H 0.2843 0.2404 0.2218 0.043 Uiso 1 1 calc R . . C29 C 0.2096(2) 0.1942(3) 0.4188(2) 0.0225(6) Uani 1 1 d . . . C30 C 0.1851(3) 0.0551(3) 0.4192(2) 0.0341(8) Uani 1 1 d . . . H30A H 0.2029 0.0159 0.3632 0.051 Uiso 1 1 calc R . . H30B H 0.1146 0.0445 0.4192 0.051 Uiso 1 1 calc R . . H30C H 0.2221 0.0165 0.4755 0.051 Uiso 1 1 calc R . . C31 C 0.3160(2) 0.2097(3) 0.4190(2) 0.0268(7) Uani 1 1 d . . . C32 C 0.2089(2) 0.4115(3) 0.5419(2) 0.0277(7) Uani 1 1 d . . . C33 C 0.1321(3) 0.4976(4) 0.5288(2) 0.0340(8) Uani 1 1 d . . . H33 H 0.0659 0.4715 0.5118 0.041 Uiso 1 1 calc R . . C34 C 0.1551(3) 0.6209(4) 0.5411(3) 0.0430(10) Uani 1 1 d . . . H34 H 0.1042 0.6808 0.5336 0.052 Uiso 1 1 calc R . . C35 C 0.2510(3) 0.6582(4) 0.5641(3) 0.0470(10) Uani 1 1 d . . . H35 H 0.2658 0.7438 0.5712 0.056 Uiso 1 1 calc R . . C36 C 0.3258(3) 0.5728(4) 0.5771(3) 0.0442(10) Uani 1 1 d . . . H36 H 0.3918 0.5998 0.5929 0.053 Uiso 1 1 calc R . . C37 C 0.3053(3) 0.4481(4) 0.5672(2) 0.0348(8) Uani 1 1 d . . . H37 H 0.3566 0.3886 0.5776 0.042 Uiso 1 1 calc R . . C38 C 0.1110(2) 0.4796(3) 0.3031(2) 0.0239(6) Uani 1 1 d . . . C39 C 0.1008(2) 0.6901(3) 0.2391(2) 0.0288(7) Uani 1 1 d . . . C40 C 0.0459(4) 0.6505(5) 0.1437(3) 0.0612(13) Uani 1 1 d . . . H40A H 0.0914 0.6093 0.1083 0.092 Uiso 1 1 calc R . . H40B H 0.0177 0.7234 0.1091 0.092 Uiso 1 1 calc R . . H40C H -0.0069 0.5931 0.1524 0.092 Uiso 1 1 calc R . . C41 C 0.1820(3) 0.7799(4) 0.2281(3) 0.0423(9) Uani 1 1 d . . . H41A H 0.2204 0.7979 0.2898 0.063 Uiso 1 1 calc R . . H41B H 0.1535 0.8567 0.1997 0.063 Uiso 1 1 calc R . . H41C H 0.2247 0.7432 0.1876 0.063 Uiso 1 1 calc R . . C42 C 0.0340(3) 0.7449(5) 0.3019(3) 0.0560(12) Uani 1 1 d . . . H42A H -0.0153 0.6834 0.3123 0.084 Uiso 1 1 calc R . . H42B H 0.0011 0.8182 0.2717 0.084 Uiso 1 1 calc R . . H42C H 0.0729 0.7684 0.3622 0.084 Uiso 1 1 calc R . . N1 N 0.36294(18) 0.1409(2) 0.80617(17) 0.0216(5) Uani 1 1 d . . . H41 H 0.3466 0.1508 0.7452 0.026 Uiso 1 1 calc R . . N2 N 0.3697(2) -0.0507(3) 0.6052(2) 0.0429(8) Uani 1 1 d . . . N3 N 0.17913(18) 0.3902(3) 0.32884(17) 0.0222(5) Uani 1 1 d . . . H42 H 0.2418 0.4095 0.3419 0.027 Uiso 1 1 calc R . . N4 N 0.3966(2) 0.2170(3) 0.4156(2) 0.0393(7) Uani 1 1 d . . . O1 O 0.61957(18) 0.0495(3) 0.87438(17) 0.0447(7) Uani 1 1 d . . . O2 O 0.62829(18) -0.0448(3) 0.7195(2) 0.0473(7) Uani 1 1 d . . . O3 O 0.39606(17) 0.2395(2) 0.94645(15) 0.0344(6) Uani 1 1 d . . . O4 O 0.29652(17) 0.3229(2) 0.82113(15) 0.0311(5) Uani 1 1 d . . . O5 O 0.2429(2) 0.1872(3) 0.60340(17) 0.0503(7) Uani 1 1 d . . . O6 O 0.0759(2) 0.2392(3) 0.52180(18) 0.0493(7) Uani 1 1 d . . . O7 O 0.02361(16) 0.4655(3) 0.30024(19) 0.0392(6) Uani 1 1 d . . . O8 O 0.15602(15) 0.5840(2) 0.28429(16) 0.0275(5) Uani 1 1 d . . . S1 S 0.57890(5) 0.03251(8) 0.77794(5) 0.02514(17) Uani 1 1 d . . . S2 S 0.17997(6) 0.25294(9) 0.53122(5) 0.03159(19) 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 0.0225(12) 0.0166(14) 0.0199(13) 0.0008(12) 0.0047(10) 0.0024(12) C2 0.0257(14) 0.0143(14) 0.0220(14) -0.0032(12) 0.0051(11) 0.0024(12) C3 0.0256(15) 0.0338(19) 0.0244(15) 0.0021(14) 0.0043(12) -0.0008(13) C4 0.0449(19) 0.031(2) 0.0249(16) 0.0061(14) 0.0096(14) -0.0015(15) C5 0.0330(17) 0.0251(18) 0.0403(18) -0.0052(15) 0.0192(14) -0.0037(14) C6 0.0234(15) 0.0273(19) 0.045(2) -0.0024(16) 0.0005(14) 0.0011(13) C7 0.0324(16) 0.0272(18) 0.0255(15) 0.0062(14) -0.0010(12) 0.0013(14) C8 0.0175(12) 0.0190(15) 0.0277(14) -0.0008(12) 0.0072(11) -0.0006(11) C9 0.0334(17) 0.0213(17) 0.049(2) 0.0041(16) 0.0188(15) 0.0061(14) C10 0.0243(14) 0.0193(16) 0.0340(17) -0.0092(14) 0.0096(12) 0.0014(12) C11 0.0219(14) 0.0259(17) 0.0282(15) 0.0037(14) 0.0003(12) -0.0008(12) C12 0.0261(16) 0.0279(19) 0.053(2) -0.0069(17) 0.0108(15) -0.0044(14) C13 0.032(2) 0.023(2) 0.126(5) -0.002(3) 0.018(2) -0.0002(16) C14 0.0253(19) 0.055(3) 0.126(5) 0.053(3) 0.007(2) -0.005(2) C15 0.040(2) 0.079(4) 0.058(3) 0.041(3) -0.005(2) -0.019(2) C16 0.0358(18) 0.054(3) 0.0294(17) 0.0093(18) 0.0005(14) -0.0155(18) C17 0.0251(14) 0.0197(16) 0.0265(14) -0.0001(13) 0.0061(12) 0.0019(12) C18 0.0386(17) 0.0205(16) 0.0269(15) -0.0058(14) 0.0057(13) 0.0094(14) C19 0.0384(18) 0.035(2) 0.0344(18) -0.0066(16) 0.0126(15) 0.0006(16) C20 0.069(3) 0.037(2) 0.0328(18) -0.0072(17) -0.0003(17) 0.025(2) C21 0.053(2) 0.024(2) 0.048(2) -0.0096(17) 0.0219(18) -0.0031(16) C22 0.0226(13) 0.0241(16) 0.0214(13) -0.0044(13) 0.0023(11) -0.0039(12) C23 0.0338(16) 0.0217(16) 0.0190(13) 0.0005(13) -0.0012(12) 0.0002(13) C24 0.0361(18) 0.0280(19) 0.0348(18) -0.0021(15) -0.0062(14) 0.0038(15) C25 0.054(2) 0.030(2) 0.042(2) -0.0111(17) -0.0211(18) 0.0035(17) C26 0.084(3) 0.033(2) 0.0217(16) -0.0079(16) -0.0094(18) 0.020(2) C27 0.070(3) 0.038(2) 0.0297(18) -0.0012(17) 0.0186(18) 0.007(2) C28 0.048(2) 0.035(2) 0.0266(16) -0.0048(15) 0.0093(14) -0.0079(17) C29 0.0306(15) 0.0200(16) 0.0167(12) -0.0030(12) 0.0037(11) -0.0054(12) C30 0.051(2) 0.0216(19) 0.0275(16) -0.0007(14) 0.0004(14) -0.0071(15) C31 0.0352(17) 0.0207(16) 0.0225(14) -0.0033(13) -0.0014(12) 0.0022(13) C32 0.0357(16) 0.0312(19) 0.0154(13) -0.0042(13) 0.0016(12) -0.0029(14) C33 0.0332(17) 0.047(2) 0.0201(15) -0.0073(15) 0.0000(13) 0.0045(15) C34 0.057(2) 0.040(2) 0.0300(18) -0.0005(17) 0.0018(17) 0.0174(19) C35 0.066(3) 0.034(2) 0.039(2) -0.0027(18) 0.0061(19) -0.002(2) C36 0.045(2) 0.042(3) 0.045(2) -0.0112(19) 0.0065(17) -0.0066(18) C37 0.0347(17) 0.038(2) 0.0310(17) -0.0084(16) 0.0032(14) 0.0038(16) C38 0.0241(14) 0.0294(18) 0.0173(13) -0.0041(13) 0.0010(11) -0.0007(13) C39 0.0290(15) 0.0302(18) 0.0267(15) 0.0069(14) 0.0032(12) 0.0092(14) C40 0.076(3) 0.063(3) 0.035(2) 0.011(2) -0.017(2) -0.004(3) C41 0.0414(19) 0.032(2) 0.053(2) 0.0150(18) 0.0059(17) 0.0054(16) C42 0.060(3) 0.051(3) 0.065(3) 0.015(2) 0.036(2) 0.027(2) N1 0.0302(13) 0.0181(14) 0.0170(11) 0.0002(10) 0.0049(10) 0.0024(10) N2 0.0481(18) 0.046(2) 0.0340(16) -0.0144(16) 0.0057(14) 0.0015(16) N3 0.0206(11) 0.0231(14) 0.0222(12) -0.0015(11) 0.0011(10) -0.0037(10) N4 0.0335(16) 0.037(2) 0.0441(17) -0.0038(14) -0.0022(13) 0.0027(13) O1 0.0364(13) 0.055(2) 0.0373(13) 0.0192(14) -0.0091(10) -0.0106(13) O2 0.0362(13) 0.0323(15) 0.080(2) 0.0010(15) 0.0296(13) 0.0023(12) O3 0.0450(13) 0.0296(14) 0.0249(10) -0.0069(11) -0.0054(10) 0.0110(11) O4 0.0460(14) 0.0229(13) 0.0222(11) -0.0074(10) -0.0009(10) 0.0110(11) O5 0.087(2) 0.0404(17) 0.0209(12) 0.0027(12) 0.0026(12) -0.0001(16) O6 0.0537(16) 0.061(2) 0.0390(14) -0.0083(14) 0.0249(12) -0.0228(15) O7 0.0261(11) 0.0383(16) 0.0519(15) 0.0035(13) 0.0030(10) -0.0016(11) O8 0.0250(11) 0.0235(12) 0.0337(12) 0.0055(10) 0.0042(9) 0.0034(9) S1 0.0191(3) 0.0231(4) 0.0332(4) 0.0054(3) 0.0042(3) 0.0011(3) S2 0.0436(5) 0.0331(5) 0.0190(3) -0.0025(4) 0.0081(3) -0.0077(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.451(4) . ? C1 C2 1.516(4) . ? C1 C8 1.557(4) . ? C2 C3 1.390(4) . ? C2 C7 1.394(4) . ? C3 C4 1.387(5) . ? C4 C5 1.379(5) . ? C5 C6 1.373(5) . ? C6 C7 1.394(5) . ? C8 C10 1.465(4) . ? C8 C9 1.540(5) . ? C8 S1 1.853(3) . ? C10 N2 1.133(4) . ? C11 C16 1.381(5) . ? C11 C12 1.381(5) . ? C11 S1 1.760(3) . ? C12 C13 1.383(6) . ? C13 C14 1.375(8) . ? C14 C15 1.363(8) . ? C15 C16 1.377(6) . ? C17 O3 1.205(4) . ? C17 O4 1.334(4) . ? C17 N1 1.364(4) . ? C18 O4 1.485(4) . ? C18 C19 1.509(5) . ? C18 C21 1.511(5) . ? C18 C20 1.516(5) . ? C22 N3 1.450(4) . ? C22 C23 1.531(4) . ? C22 C29 1.553(4) . ? C23 C28 1.382(5) . ? C23 C24 1.388(5) . ? C24 C25 1.394(5) . ? C25 C26 1.374(6) . ? C26 C27 1.375(6) . ? C27 C28 1.388(5) . ? C29 C31 1.479(4) . ? C29 C30 1.542(5) . ? C29 S2 1.851(3) . ? C31 N4 1.126(4) . ? C32 C37 1.381(5) . ? C32 C33 1.400(5) . ? C32 S2 1.761(4) . ? C33 C34 1.375(6) . ? C34 C35 1.372(6) . ? C35 C36 1.375(6) . ? C36 C37 1.380(6) . ? C38 O7 1.211(4) . ? C38 O8 1.339(4) . ? C38 N3 1.358(4) . ? C39 O8 1.470(4) . ? C39 C41 1.511(5) . ? C39 C42 1.516(5) . ? C39 C40 1.522(5) . ? O1 S1 1.426(3) . ? O2 S1 1.436(3) . ? O5 S2 1.432(3) . ? O6 S2 1.429(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 N1 C1 C2 112.5(2) . . ? N1 C1 C8 110.9(2) . . ? C2 C1 C8 112.7(2) . . ? C3 C2 C7 118.7(3) . . ? C3 C2 C1 119.5(3) . . ? C7 C2 C1 121.9(3) . . ? C4 C3 C2 120.6(3) . . ? C5 C4 C3 120.2(3) . . ? C6 C5 C4 120.0(3) . . ? C5 C6 C7 120.3(3) . . ? C2 C7 C6 120.2(3) . . ? C10 C8 C9 109.5(3) . . ? C10 C8 C1 112.5(2) . . ? C9 C8 C1 112.3(2) . . ? C10 C8 S1 107.2(2) . . ? C9 C8 S1 104.2(2) . . ? C1 C8 S1 110.7(2) . . ? N2 C10 C8 178.7(4) . . ? C16 C11 C12 121.9(4) . . ? C16 C11 S1 118.4(3) . . ? C12 C11 S1 119.3(3) . . ? C11 C12 C13 118.0(4) . . ? C14 C13 C12 120.3(5) . . ? C15 C14 C13 120.8(4) . . ? C14 C15 C16 120.3(4) . . ? C15 C16 C11 118.7(4) . . ? O3 C17 O4 127.0(3) . . ? O3 C17 N1 124.0(3) . . ? O4 C17 N1 109.0(2) . . ? O4 C18 C19 110.1(3) . . ? O4 C18 C21 109.3(3) . . ? C19 C18 C21 113.4(3) . . ? O4 C18 C20 101.7(3) . . ? C19 C18 C20 110.5(3) . . ? C21 C18 C20 111.2(3) . . ? N3 C22 C23 111.4(2) . . ? N3 C22 C29 111.6(2) . . ? C23 C22 C29 112.7(3) . . ? C28 C23 C24 119.2(3) . . ? C28 C23 C22 121.5(3) . . ? C24 C23 C22 119.3(3) . . ? C23 C24 C25 120.0(4) . . ? C26 C25 C24 120.2(4) . . ? C25 C26 C27 120.0(3) . . ? C26 C27 C28 120.2(4) . . ? C23 C28 C27 120.4(4) . . ? C31 C29 C30 109.2(3) . . ? C31 C29 C22 111.5(2) . . ? C30 C29 C22 112.1(3) . . ? C31 C29 S2 108.7(2) . . ? C30 C29 S2 104.5(2) . . ? C22 C29 S2 110.5(2) . . ? N4 C31 C29 176.4(3) . . ? C37 C32 C33 121.5(3) . . ? C37 C32 S2 119.8(3) . . ? C33 C32 S2 118.6(3) . . ? C34 C33 C32 118.2(3) . . ? C35 C34 C33 120.6(4) . . ? C34 C35 C36 120.7(4) . . ? C35 C36 C37 120.3(4) . . ? C36 C37 C32 118.7(4) . . ? O7 C38 O8 126.4(3) . . ? O7 C38 N3 124.3(3) . . ? O8 C38 N3 109.3(2) . . ? O8 C39 C41 101.9(2) . . ? O8 C39 C42 111.2(3) . . ? C41 C39 C42 110.4(3) . . ? O8 C39 C40 109.1(3) . . ? C41 C39 C40 110.7(3) . . ? C42 C39 C40 112.9(4) . . ? C17 N1 C1 118.5(2) . . ? C38 N3 C22 119.5(2) . . ? C17 O4 C18 120.8(2) . . ? C38 O8 C39 121.5(2) . . ? O1 S1 O2 119.95(18) . . ? O1 S1 C11 108.27(17) . . ? O2 S1 C11 107.50(16) . . ? O1 S1 C8 105.49(14) . . ? O2 S1 C8 104.31(15) . . ? C11 S1 C8 111.21(14) . . ? O6 S2 O5 119.94(18) . . ? O6 S2 C32 108.64(18) . . ? O5 S2 C32 108.48(17) . . ? O6 S2 C29 104.14(15) . . ? O5 S2 C29 105.88(16) . . ? C32 S2 C29 109.34(15) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.561 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.063 # Attachment '- 4j minor.cif' data_2125ago _database_code_depnum_ccdc_archive 'CCDC 867729' #TrackingRef '- 4j minor.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H23 Cl N2 O4 S' _chemical_formula_weight 434.92 _chemical_absolute_configuration S,R 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.911(4) _cell_length_b 9.919(4) _cell_length_c 24.452(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2161.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9738 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.20 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9147 _exptl_absorpt_correction_T_max 0.9704 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15486 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.24 _reflns_number_total 5319 _reflns_number_gt 5149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.2011P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(4) _refine_ls_number_reflns 5319 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 C1 C 0.87468(15) 0.25406(13) 0.88339(5) 0.0175(2) Uani 1 1 d . . . H1 H 0.8267 0.3063 0.8531 0.021 Uiso 1 1 calc R . . C2 C 0.99477(15) 0.16459(13) 0.85790(5) 0.0178(2) Uani 1 1 d . . . C3 C 1.11857(15) 0.12286(13) 0.88848(6) 0.0204(3) Uani 1 1 d . . . H3 H 1.1266 0.1490 0.9257 0.024 Uiso 1 1 calc R . . C4 C 1.23041(16) 0.04350(14) 0.86519(6) 0.0237(3) Uani 1 1 d . . . H4 H 1.3139 0.0156 0.8865 0.028 Uiso 1 1 calc R . . C5 C 1.21984(17) 0.00510(16) 0.81065(7) 0.0281(3) Uani 1 1 d . . . H5 H 1.2951 -0.0507 0.7950 0.034 Uiso 1 1 calc R . . C6 C 1.10003(19) 0.04783(16) 0.77907(6) 0.0284(3) Uani 1 1 d . . . H6 H 1.0930 0.0227 0.7417 0.034 Uiso 1 1 calc R . . C7 C 0.99030(16) 0.12795(14) 0.80282(6) 0.0213(3) Uani 1 1 d . . . C8 C 0.74839(14) 0.17100(14) 0.91207(5) 0.0179(2) Uani 1 1 d . . . C9 C 0.79572(16) 0.09529(15) 0.96416(6) 0.0228(3) Uani 1 1 d . . . H9A H 0.7108 0.0424 0.9779 0.034 Uiso 1 1 calc R . . H9B H 0.8269 0.1604 0.9921 0.034 Uiso 1 1 calc R . . H9C H 0.8796 0.0348 0.9557 0.034 Uiso 1 1 calc R . . C10 C 0.68264(16) 0.07276(14) 0.87368(6) 0.0213(3) Uani 1 1 d . . . C11 C 0.55347(16) 0.38896(15) 0.87758(6) 0.0221(3) Uani 1 1 d . . . C12 C 0.61969(17) 0.51592(16) 0.87598(7) 0.0277(3) Uani 1 1 d . . . H12 H 0.6841 0.5451 0.9046 0.033 Uiso 1 1 calc R . . C13 C 0.5895(2) 0.59893(17) 0.83173(7) 0.0352(4) Uani 1 1 d . . . H13 H 0.6334 0.6861 0.8298 0.042 Uiso 1 1 calc R . . C14 C 0.4953(2) 0.5548(2) 0.79031(7) 0.0369(4) Uani 1 1 d . . . H14 H 0.4762 0.6119 0.7599 0.044 Uiso 1 1 calc R . . C15 C 0.4289(2) 0.42930(19) 0.79261(7) 0.0368(4) Uani 1 1 d . . . H15 H 0.3638 0.4007 0.7641 0.044 Uiso 1 1 calc R . . C16 C 0.45759(19) 0.34463(17) 0.83685(6) 0.0297(3) Uani 1 1 d . . . H16 H 0.4122 0.2581 0.8390 0.036 Uiso 1 1 calc R . . C17 C 0.99444(15) 0.46636(14) 0.90076(6) 0.0207(3) Uani 1 1 d . . . C18 C 1.08207(17) 0.68916(14) 0.92776(6) 0.0259(3) Uani 1 1 d . . . C19 C 1.23583(18) 0.67525(17) 0.90117(8) 0.0341(4) Uani 1 1 d . . . H19A H 1.3004 0.6191 0.9243 0.051 Uiso 1 1 calc R . . H19B H 1.2811 0.7647 0.8970 0.051 Uiso 1 1 calc R . . H19C H 1.2249 0.6330 0.8651 0.051 Uiso 1 1 calc R . . C20 C 0.96970(19) 0.76316(15) 0.89194(8) 0.0324(3) Uani 1 1 d . . . H20A H 0.9640 0.7190 0.8561 0.049 Uiso 1 1 calc R . . H20B H 1.0019 0.8569 0.8872 0.049 Uiso 1 1 calc R . . H20C H 0.8707 0.7613 0.9094 0.049 Uiso 1 1 calc R . . C21 C 1.0937(2) 0.75608(17) 0.98368(8) 0.0372(4) Uani 1 1 d . . . H21A H 0.9950 0.7557 1.0014 0.056 Uiso 1 1 calc R . . H21B H 1.1281 0.8493 0.9793 0.056 Uiso 1 1 calc R . . H21C H 1.1654 0.7063 1.0064 0.056 Uiso 1 1 calc R . . Cl1 Cl 0.84750(5) 0.18687(4) 0.760321(14) 0.03162(10) Uani 1 1 d . . . N1 N 0.93677(13) 0.35094(11) 0.92172(5) 0.0198(2) Uani 1 1 d . . . H23 H 0.9370 0.3354 0.9571 0.024 Uiso 1 1 calc R . . N2 N 0.62987(16) -0.00803(15) 0.84649(6) 0.0334(3) Uani 1 1 d . . . O1 O 1.01223(14) 0.48554(11) 0.85235(4) 0.0315(3) Uani 1 1 d . . . O2 O 1.02456(12) 0.55338(10) 0.94155(4) 0.0243(2) Uani 1 1 d . . . O3 O 0.64986(12) 0.36505(11) 0.97765(4) 0.0260(2) Uani 1 1 d . . . O4 O 0.46674(11) 0.19650(11) 0.94413(4) 0.0258(2) Uani 1 1 d . . . S1 S 0.59295(4) 0.28338(3) 0.933605(13) 0.01920(8) 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 0.0209(6) 0.0172(6) 0.0143(5) 0.0000(5) 0.0002(5) -0.0021(4) C2 0.0199(6) 0.0168(6) 0.0168(6) -0.0015(5) 0.0016(5) -0.0031(5) C3 0.0221(6) 0.0190(6) 0.0201(6) -0.0010(5) 0.0000(5) -0.0039(5) C4 0.0200(6) 0.0200(6) 0.0310(7) -0.0007(6) 0.0001(6) -0.0020(5) C5 0.0272(7) 0.0249(7) 0.0323(8) -0.0058(6) 0.0087(6) -0.0002(6) C6 0.0356(8) 0.0280(7) 0.0215(6) -0.0060(6) 0.0053(6) -0.0012(6) C7 0.0249(6) 0.0232(6) 0.0159(6) -0.0006(5) -0.0020(5) -0.0030(5) C8 0.0185(6) 0.0185(6) 0.0167(6) -0.0018(5) -0.0002(5) -0.0011(5) C9 0.0260(7) 0.0235(6) 0.0188(6) 0.0044(5) -0.0015(5) -0.0025(5) C10 0.0234(6) 0.0218(6) 0.0187(6) -0.0024(5) 0.0020(5) -0.0023(5) C11 0.0219(6) 0.0246(6) 0.0198(6) 0.0026(5) 0.0013(5) 0.0033(5) C12 0.0262(7) 0.0253(7) 0.0314(7) 0.0016(6) -0.0007(6) 0.0015(6) C13 0.0321(8) 0.0291(8) 0.0445(10) 0.0125(7) 0.0061(8) 0.0033(7) C14 0.0331(8) 0.0469(10) 0.0308(8) 0.0161(8) 0.0024(7) 0.0109(8) C15 0.0366(9) 0.0475(10) 0.0263(8) 0.0036(7) -0.0070(7) 0.0044(8) C16 0.0316(7) 0.0324(8) 0.0251(7) 0.0017(6) -0.0031(6) 0.0006(6) C17 0.0233(6) 0.0179(6) 0.0209(6) -0.0002(5) 0.0017(6) -0.0020(5) C18 0.0294(7) 0.0169(6) 0.0315(7) -0.0017(6) 0.0026(6) -0.0037(5) C19 0.0294(8) 0.0262(8) 0.0467(10) -0.0002(7) 0.0044(7) -0.0035(6) C20 0.0312(8) 0.0219(7) 0.0441(9) 0.0044(7) -0.0011(7) -0.0019(6) C21 0.0482(9) 0.0239(7) 0.0395(9) -0.0094(7) -0.0036(8) -0.0051(7) Cl1 0.0370(2) 0.0413(2) 0.01660(15) -0.00121(14) -0.00607(14) 0.00434(16) N1 0.0276(6) 0.0177(5) 0.0143(5) -0.0013(4) 0.0008(4) -0.0038(4) N2 0.0359(7) 0.0327(7) 0.0317(7) -0.0074(6) 0.0004(6) -0.0072(6) O1 0.0485(7) 0.0287(6) 0.0173(5) 0.0016(4) 0.0035(5) -0.0109(5) O2 0.0352(5) 0.0168(4) 0.0207(5) -0.0026(4) 0.0030(4) -0.0056(4) O3 0.0315(5) 0.0294(5) 0.0171(4) -0.0064(4) 0.0013(4) -0.0003(4) O4 0.0231(5) 0.0309(5) 0.0235(5) 0.0010(4) 0.0043(4) -0.0033(4) S1 0.02056(15) 0.02239(16) 0.01466(14) -0.00081(12) 0.00192(12) -0.00064(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 C1 N1 1.4519(17) . ? C1 C2 1.5236(19) . ? C1 C8 1.5610(18) . ? C2 C7 1.3954(19) . ? C2 C3 1.396(2) . ? C3 C4 1.392(2) . ? C4 C5 1.390(2) . ? C5 C6 1.384(2) . ? C6 C7 1.387(2) . ? C7 Cl1 1.7437(15) . ? C8 C10 1.4744(19) . ? C8 C9 1.5374(19) . ? C8 S1 1.8542(15) . ? C10 N2 1.142(2) . ? C11 C16 1.384(2) . ? C11 C12 1.391(2) . ? C11 S1 1.7599(15) . ? C12 C13 1.386(2) . ? C13 C14 1.386(3) . ? C14 C15 1.380(3) . ? C15 C16 1.393(2) . ? C17 O1 1.2095(18) . ? C17 O2 1.3461(17) . ? C17 N1 1.3554(18) . ? C18 O2 1.4798(18) . ? C18 C20 1.519(2) . ? C18 C19 1.523(2) . ? C18 C21 1.524(2) . ? O3 S1 1.4398(11) . ? O4 S1 1.4400(11) . ? 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 112.46(11) . . ? N1 C1 C8 109.51(11) . . ? C2 C1 C8 112.50(11) . . ? C7 C2 C3 117.55(13) . . ? C7 C2 C1 121.77(12) . . ? C3 C2 C1 120.58(12) . . ? C4 C3 C2 120.96(13) . . ? C5 C4 C3 119.93(14) . . ? C6 C5 C4 120.24(14) . . ? C5 C6 C7 119.05(14) . . ? C6 C7 C2 122.21(14) . . ? C6 C7 Cl1 117.18(11) . . ? C2 C7 Cl1 120.58(11) . . ? C10 C8 C9 108.27(12) . . ? C10 C8 C1 110.44(11) . . ? C9 C8 C1 115.61(11) . . ? C10 C8 S1 106.33(9) . . ? C9 C8 S1 105.27(9) . . ? C1 C8 S1 110.41(10) . . ? N2 C10 C8 176.01(16) . . ? C16 C11 C12 121.96(14) . . ? C16 C11 S1 119.64(12) . . ? C12 C11 S1 118.40(12) . . ? C13 C12 C11 118.51(15) . . ? C12 C13 C14 120.03(16) . . ? C15 C14 C13 120.98(16) . . ? C14 C15 C16 119.78(16) . . ? C11 C16 C15 118.73(16) . . ? O1 C17 O2 126.75(13) . . ? O1 C17 N1 123.55(13) . . ? O2 C17 N1 109.70(12) . . ? O2 C18 C20 110.05(12) . . ? O2 C18 C19 109.05(12) . . ? C20 C18 C19 112.99(14) . . ? O2 C18 C21 102.44(12) . . ? C20 C18 C21 110.59(14) . . ? C19 C18 C21 111.20(14) . . ? C17 N1 C1 117.35(11) . . ? C17 O2 C18 118.93(11) . . ? O3 S1 O4 118.56(7) . . ? O3 S1 C11 108.53(8) . . ? O4 S1 C11 109.82(7) . . ? O3 S1 C8 106.71(7) . . ? O4 S1 C8 105.93(7) . . ? C11 S1 C8 106.62(7) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.320 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.069