# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Min Shi' _publ_contact_author_email MSHI@MAIL.SIOC.AC.CN _publ_section_title ; Recent extensions of Morita-Baylis-Hillman reaction ; loop_ _publ_author_name 'Min Shi' 'Jia-Jun Jiang' 'Guang-Ning Ma' 'Yin Wei' # Attachment 'cd28526.cif' data_cd28526 _database_code_depnum_ccdc_archive 'CCDC 710496' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Cl N O3 S' _chemical_formula_weight 387.86 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.333(5) _cell_length_b 8.0254(15) _cell_length_c 21.292(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.925(4) _cell_angle_gamma 90.00 _cell_volume 3800.8(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3007 _cell_measurement_theta_min 5.205 _cell_measurement_theta_max 43.085 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.475 _exptl_crystal_size_mid 0.366 _exptl_crystal_size_min 0.157 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7787 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 19188 _diffrn_reflns_av_R_equivalents 0.1307 _diffrn_reflns_av_sigmaI/netI 0.1162 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7054 _reflns_number_gt 4265 _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^)+(0.1235P)^2^+10.3257P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7054 _refine_ls_number_parameters 472 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1412 _refine_ls_R_factor_gt 0.1032 _refine_ls_wR_factor_ref 0.3099 _refine_ls_wR_factor_gt 0.2926 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 0.43203(8) -0.0477(2) 0.12968(8) 0.0414(5) Uani 1 1 d . . . S2 S 0.06645(8) -0.0782(2) 0.19237(9) 0.0450(5) Uani 1 1 d . . . Cl1 Cl 0.57178(10) 0.3920(3) 0.01503(10) 0.0764(7) Uani 1 1 d . . . Cl2 Cl -0.07872(11) 0.4071(3) -0.05622(11) 0.0761(7) Uani 1 1 d . . . N1 N 0.4565(2) 0.0915(6) 0.1910(3) 0.0386(12) Uani 1 1 d . . . N2 N 0.0392(2) 0.0622(7) 0.2276(3) 0.0407(13) Uani 1 1 d . . . O1 O 0.4835(2) -0.1414(6) 0.1347(2) 0.0556(13) Uani 1 1 d . . . O2 O 0.3841(2) -0.1321(6) 0.1383(2) 0.0550(13) Uani 1 1 d . . . O3 O 0.3092(3) 0.4061(8) 0.1684(4) 0.085(2) Uani 1 1 d . . . O4 O 0.0159(2) -0.1720(6) 0.1468(3) 0.0568(13) Uani 1 1 d . . . O5 O 0.1128(2) -0.1629(6) 0.2473(3) 0.0632(15) Uani 1 1 d . . . O6 O 0.1824(3) 0.3918(9) 0.3433(4) 0.095(2) Uani 1 1 d . . . C1 C 0.5133(3) 0.1794(8) 0.2025(3) 0.0386(15) Uani 1 1 d . . . H1A H 0.5387 0.1069 0.1892 0.046 Uiso 1 1 calc R . . H1B H 0.5344 0.2038 0.2510 0.046 Uiso 1 1 calc R . . C2 C 0.5028(3) 0.3391(8) 0.1624(3) 0.0396(15) Uani 1 1 d . . . C3 C 0.4466(3) 0.4226(8) 0.1486(3) 0.0368(14) Uani 1 1 d . . . H3 H 0.4391 0.5237 0.1254 0.044 Uiso 1 1 calc R . . C4 C 0.4049(3) 0.3606(8) 0.1679(3) 0.0411(15) Uani 1 1 d . . . C5 C 0.4124(3) 0.1955(9) 0.2031(4) 0.0479(17) Uani 1 1 d . . . H5A H 0.4254 0.2129 0.2521 0.057 Uiso 1 1 calc R . . H5B H 0.3740 0.1382 0.1863 0.057 Uiso 1 1 calc R . . C6 C 0.3499(3) 0.4544(10) 0.1538(4) 0.061(2) Uani 1 1 d . . . H6 H 0.3457 0.5575 0.1323 0.073 Uiso 1 1 calc R . . C7 C 0.5420(3) 0.4021(8) 0.1388(3) 0.0412(15) Uani 1 1 d . . . H7 H 0.5300 0.4980 0.1121 0.049 Uiso 1 1 calc R . . C8 C 0.6014(3) 0.3360(8) 0.1505(3) 0.0423(15) Uani 1 1 d . . . C9 C 0.6425(3) 0.2847(11) 0.2136(4) 0.061(2) Uani 1 1 d . . . H9 H 0.6318 0.2886 0.2508 0.074 Uiso 1 1 calc R . . C10 C 0.6995(4) 0.2273(14) 0.2244(5) 0.086(3) Uani 1 1 d . . . H10 H 0.7262 0.1925 0.2677 0.103 Uiso 1 1 calc R . . C11 C 0.7155(4) 0.2231(13) 0.1697(5) 0.083(3) Uani 1 1 d . . . H11 H 0.7535 0.1848 0.1759 0.100 Uiso 1 1 calc R . . C12 C 0.6765(4) 0.2743(12) 0.1063(4) 0.071(2) Uani 1 1 d . . . H12 H 0.6879 0.2712 0.0695 0.086 Uiso 1 1 calc R . . C13 C 0.6205(3) 0.3304(9) 0.0965(3) 0.0496(18) Uani 1 1 d . . . C14 C 0.4011(3) 0.0512(8) 0.0493(3) 0.0376(14) Uani 1 1 d . . . C15 C 0.4368(3) 0.0806(10) 0.0140(4) 0.0540(19) Uani 1 1 d . . . H15 H 0.4776 0.0555 0.0338 0.065 Uiso 1 1 calc R . . C16 C 0.4108(4) 0.1477(11) -0.0510(4) 0.064(2) Uani 1 1 d . . . H16 H 0.4349 0.1653 -0.0750 0.076 Uiso 1 1 calc R . . C17 C 0.3506(4) 0.1902(9) -0.0822(3) 0.0546(19) Uani 1 1 d . . . C18 C 0.3178(3) 0.1646(11) -0.0437(4) 0.063(2) Uani 1 1 d . . . H18 H 0.2774 0.1955 -0.0620 0.076 Uiso 1 1 calc R . . C19 C 0.3419(3) 0.0953(10) 0.0209(3) 0.0533(19) Uani 1 1 d . . . H19 H 0.3180 0.0787 0.0451 0.064 Uiso 1 1 calc R . . C20 C 0.3234(4) 0.2521(12) -0.1545(4) 0.082(3) Uani 1 1 d . . . H20A H 0.3112 0.1591 -0.1855 0.123 Uiso 1 1 calc R . . H20B H 0.3525 0.3172 -0.1635 0.123 Uiso 1 1 calc R . . H20C H 0.2890 0.3200 -0.1610 0.123 Uiso 1 1 calc R . . C21 C -0.0177(3) 0.1470(8) 0.1846(3) 0.0410(15) Uani 1 1 d . . . H21A H -0.0400 0.1707 0.2123 0.049 Uiso 1 1 calc R . . H21B H -0.0419 0.0731 0.1477 0.049 Uiso 1 1 calc R . . C22 C -0.0071(3) 0.3075(8) 0.1542(3) 0.0361(14) Uani 1 1 d . . . C23 C 0.0482(3) 0.3919(8) 0.1933(3) 0.0410(15) Uani 1 1 d . . . H23 H 0.0555 0.4933 0.1770 0.049 Uiso 1 1 calc R . . C24 C 0.0896(3) 0.3329(8) 0.2517(3) 0.0417(15) Uani 1 1 d . . . C25 C 0.0819(3) 0.1689(9) 0.2806(3) 0.0478(17) Uani 1 1 d . . . H25A H 0.1205 0.1130 0.3009 0.057 Uiso 1 1 calc R . . H25B H 0.0678 0.1877 0.3165 0.057 Uiso 1 1 calc R . . C26 C 0.1439(3) 0.4309(10) 0.2888(4) 0.061(2) Uani 1 1 d . . . H26 H 0.1489 0.5297 0.2689 0.074 Uiso 1 1 calc R . . C27 C -0.0467(3) 0.3754(9) 0.0953(3) 0.0434(16) Uani 1 1 d . . . H27 H -0.0348 0.4743 0.0817 0.052 Uiso 1 1 calc R . . C28 C -0.1054(3) 0.3135(8) 0.0506(3) 0.0385(15) Uani 1 1 d . . . C29 C -0.1460(3) 0.2449(11) 0.0747(4) 0.056(2) Uani 1 1 d . . . H29 H -0.1343 0.2321 0.1218 0.067 Uiso 1 1 calc R . . C30 C -0.2027(3) 0.1958(11) 0.0310(5) 0.065(2) Uani 1 1 d . . . H30 H -0.2288 0.1507 0.0484 0.078 Uiso 1 1 calc R . . C31 C -0.2206(3) 0.2138(11) -0.0385(5) 0.066(2) Uani 1 1 d . . . H31 H -0.2591 0.1814 -0.0682 0.079 Uiso 1 1 calc R . . C32 C -0.1825(4) 0.2786(10) -0.0643(4) 0.065(2) Uani 1 1 d . . . H32 H -0.1951 0.2899 -0.1115 0.078 Uiso 1 1 calc R . . C33 C -0.1254(3) 0.3277(9) -0.0210(4) 0.0486(17) Uani 1 1 d . . . C34 C 0.1002(3) 0.0214(8) 0.1439(3) 0.0429(16) Uani 1 1 d . . . C35 C 0.0663(3) 0.0599(10) 0.0766(4) 0.0555(19) Uani 1 1 d . . . H35 H 0.0256 0.0341 0.0573 0.067 Uiso 1 1 calc R . . C36 C 0.0921(4) 0.1371(10) 0.0369(4) 0.058(2) Uani 1 1 d . . . H36 H 0.0684 0.1631 -0.0088 0.070 Uiso 1 1 calc R . . C37 C 0.1524(4) 0.1754(9) 0.0644(4) 0.057(2) Uani 1 1 d . . . C38 C 0.1849(4) 0.1408(11) 0.1314(5) 0.066(2) Uani 1 1 d . . . H38 H 0.2253 0.1706 0.1507 0.079 Uiso 1 1 calc R . . C39 C 0.1608(3) 0.0628(10) 0.1730(4) 0.057(2) Uani 1 1 d . . . H39 H 0.1846 0.0391 0.2188 0.069 Uiso 1 1 calc R . . C40 C 0.1809(5) 0.2546(12) 0.0205(5) 0.082(3) Uani 1 1 d . . . H40A H 0.2141 0.3228 0.0488 0.123 Uiso 1 1 calc R . . H40B H 0.1517 0.3223 -0.0143 0.123 Uiso 1 1 calc R . . H40C H 0.1950 0.1691 -0.0008 0.123 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 0.0476(10) 0.0357(9) 0.0400(9) 0.0017(7) 0.0167(8) -0.0051(7) S2 0.0510(10) 0.0393(9) 0.0561(11) 0.0044(8) 0.0334(9) 0.0016(8) Cl1 0.0730(14) 0.1149(19) 0.0438(11) 0.0095(11) 0.0263(10) 0.0225(13) Cl2 0.0889(16) 0.0962(17) 0.0561(12) 0.0016(11) 0.0428(12) -0.0191(13) N1 0.043(3) 0.039(3) 0.037(3) 0.003(2) 0.020(2) -0.002(2) N2 0.044(3) 0.045(3) 0.040(3) 0.007(2) 0.024(3) 0.010(3) O1 0.061(3) 0.047(3) 0.052(3) -0.001(2) 0.016(2) 0.018(2) O2 0.061(3) 0.047(3) 0.054(3) 0.006(2) 0.020(2) -0.022(2) O3 0.059(4) 0.096(5) 0.121(5) -0.008(4) 0.056(4) -0.006(3) O4 0.065(3) 0.054(3) 0.068(3) -0.012(3) 0.043(3) -0.019(3) O5 0.077(4) 0.052(3) 0.072(4) 0.022(3) 0.042(3) 0.021(3) O6 0.051(4) 0.104(5) 0.089(5) -0.008(4) -0.014(3) -0.014(4) C1 0.037(3) 0.047(4) 0.034(3) 0.000(3) 0.016(3) -0.003(3) C2 0.045(4) 0.036(3) 0.035(3) -0.001(3) 0.015(3) 0.002(3) C3 0.044(4) 0.032(3) 0.036(3) 0.001(3) 0.018(3) 0.000(3) C4 0.040(4) 0.046(4) 0.039(3) -0.007(3) 0.018(3) -0.006(3) C5 0.058(4) 0.052(4) 0.047(4) 0.005(3) 0.035(4) -0.003(3) C6 0.053(5) 0.051(5) 0.080(6) -0.009(4) 0.027(4) -0.004(4) C7 0.041(4) 0.047(4) 0.038(3) 0.000(3) 0.020(3) -0.003(3) C8 0.042(4) 0.047(4) 0.040(4) 0.001(3) 0.018(3) 0.001(3) C9 0.043(4) 0.094(6) 0.043(4) 0.009(4) 0.012(3) 0.001(4) C10 0.045(5) 0.122(8) 0.077(6) 0.031(6) 0.011(5) 0.008(5) C11 0.054(5) 0.108(8) 0.091(7) 0.016(6) 0.032(5) 0.025(5) C12 0.064(5) 0.101(7) 0.061(5) 0.000(5) 0.038(5) 0.020(5) C13 0.054(4) 0.060(4) 0.043(4) -0.003(3) 0.027(3) 0.007(4) C14 0.044(4) 0.039(3) 0.035(3) -0.009(3) 0.021(3) -0.007(3) C15 0.046(4) 0.069(5) 0.057(4) 0.011(4) 0.031(4) 0.011(4) C16 0.078(6) 0.078(6) 0.046(4) 0.008(4) 0.036(4) 0.001(5) C17 0.067(5) 0.052(4) 0.034(4) 0.002(3) 0.010(4) -0.016(4) C18 0.037(4) 0.085(6) 0.057(5) 0.010(4) 0.008(4) -0.008(4) C19 0.041(4) 0.081(5) 0.037(4) 0.003(4) 0.014(3) -0.007(4) C20 0.095(7) 0.093(7) 0.038(4) 0.015(4) 0.007(4) -0.027(6) C21 0.039(4) 0.047(4) 0.047(4) 0.000(3) 0.028(3) -0.001(3) C22 0.032(3) 0.044(4) 0.042(4) -0.002(3) 0.025(3) 0.004(3) C23 0.041(4) 0.043(4) 0.042(4) -0.003(3) 0.021(3) 0.000(3) C24 0.035(3) 0.048(4) 0.041(4) -0.005(3) 0.014(3) 0.005(3) C25 0.052(4) 0.058(4) 0.038(4) 0.003(3) 0.024(3) 0.010(4) C26 0.041(4) 0.060(5) 0.075(6) -0.011(4) 0.014(4) 0.001(4) C27 0.045(4) 0.049(4) 0.044(4) -0.001(3) 0.027(3) 0.002(3) C28 0.030(3) 0.047(4) 0.041(3) 0.002(3) 0.017(3) 0.007(3) C29 0.035(4) 0.090(6) 0.049(4) 0.002(4) 0.024(3) 0.000(4) C30 0.037(4) 0.080(6) 0.076(6) 0.001(5) 0.020(4) -0.002(4) C31 0.036(4) 0.074(6) 0.072(6) -0.005(5) 0.006(4) -0.010(4) C32 0.061(5) 0.068(5) 0.049(4) -0.001(4) 0.005(4) -0.002(4) C33 0.059(5) 0.045(4) 0.043(4) 0.003(3) 0.023(4) 0.000(3) C34 0.047(4) 0.045(4) 0.047(4) -0.002(3) 0.029(3) 0.003(3) C35 0.053(4) 0.067(5) 0.049(4) 0.002(4) 0.023(4) -0.010(4) C36 0.061(5) 0.066(5) 0.052(4) 0.008(4) 0.028(4) -0.004(4) C37 0.067(5) 0.052(4) 0.074(5) 0.001(4) 0.049(5) 0.001(4) C38 0.044(4) 0.075(6) 0.088(6) 0.003(5) 0.037(5) -0.002(4) C39 0.038(4) 0.074(5) 0.059(5) -0.001(4) 0.019(4) -0.002(4) C40 0.096(7) 0.080(6) 0.106(7) 0.013(6) 0.078(6) -0.003(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 O2 1.423(5) . ? S1 O1 1.426(5) . ? S1 N1 1.636(5) . ? S1 C14 1.755(6) . ? S2 O5 1.426(5) . ? S2 O4 1.434(5) . ? S2 N2 1.635(5) . ? S2 C34 1.752(6) . ? Cl1 C13 1.729(7) . ? Cl2 C33 1.719(7) . ? N1 C5 1.462(8) . ? N1 C1 1.481(8) . ? N2 C25 1.462(9) . ? N2 C21 1.479(8) . ? O3 C6 1.215(9) . ? O6 C26 1.200(9) . ? C1 C2 1.503(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C7 1.343(9) . ? C2 C3 1.442(9) . ? C3 C4 1.337(8) . ? C3 H3 0.9300 . ? C4 C6 1.456(10) . ? C4 C5 1.496(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6 0.9300 . ? C7 C8 1.464(9) . ? C7 H7 0.9300 . ? C8 C9 1.372(10) . ? C8 C13 1.405(9) . ? C9 C10 1.389(12) . ? C9 H9 0.9300 . ? C10 C11 1.370(13) . ? C10 H10 0.9300 . ? C11 C12 1.362(12) . ? C11 H11 0.9300 . ? C12 C13 1.369(11) . ? C12 H12 0.9300 . ? C14 C19 1.363(9) . ? C14 C15 1.380(9) . ? C15 C16 1.377(10) . ? C15 H15 0.9300 . ? C16 C17 1.385(11) . ? C16 H16 0.9300 . ? C17 C18 1.373(10) . ? C17 C20 1.493(10) . ? C18 C19 1.374(10) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.509(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C27 1.349(9) . ? C22 C23 1.433(9) . ? C23 C24 1.330(9) . ? C23 H23 0.9300 . ? C24 C26 1.463(10) . ? C24 C25 1.496(9) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26 0.9300 . ? C27 C28 1.446(9) . ? C27 H27 0.9300 . ? C28 C29 1.398(9) . ? C28 C33 1.404(9) . ? C29 C30 1.372(10) . ? C29 H29 0.9300 . ? C30 C31 1.370(11) . ? C30 H30 0.9300 . ? C31 C32 1.357(12) . ? C31 H31 0.9300 . ? C32 C33 1.377(11) . ? C32 H32 0.9300 . ? C34 C35 1.367(9) . ? C34 C39 1.387(9) . ? C35 C36 1.387(10) . ? C35 H35 0.9300 . ? C36 C37 1.376(11) . ? C36 H36 0.9300 . ? C37 C38 1.349(11) . ? C37 C40 1.512(10) . ? C38 C39 1.393(11) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 118.6(3) . . ? O2 S1 N1 105.9(3) . . ? O1 S1 N1 106.0(3) . . ? O2 S1 C14 106.9(3) . . ? O1 S1 C14 109.2(3) . . ? N1 S1 C14 110.0(3) . . ? O5 S2 O4 118.8(3) . . ? O5 S2 N2 106.7(3) . . ? O4 S2 N2 106.0(3) . . ? O5 S2 C34 107.2(3) . . ? O4 S2 C34 108.7(3) . . ? N2 S2 C34 109.3(3) . . ? C5 N1 C1 113.6(5) . . ? C5 N1 S1 118.3(4) . . ? C1 N1 S1 118.1(4) . . ? C25 N2 C21 113.7(5) . . ? C25 N2 S2 117.6(4) . . ? C21 N2 S2 119.0(4) . . ? N1 C1 C2 112.4(5) . . ? N1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? N1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.9 . . ? C7 C2 C3 120.5(6) . . ? C7 C2 C1 123.4(6) . . ? C3 C2 C1 116.1(6) . . ? C4 C3 C2 122.8(6) . . ? C4 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C3 C4 C6 119.6(6) . . ? C3 C4 C5 121.9(6) . . ? C6 C4 C5 118.5(6) . . ? N1 C5 C4 111.5(5) . . ? N1 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? N1 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? O3 C6 C4 123.9(8) . . ? O3 C6 H6 118.1 . . ? C4 C6 H6 118.1 . . ? C2 C7 C8 126.9(6) . . ? C2 C7 H7 116.5 . . ? C8 C7 H7 116.5 . . ? C9 C8 C13 116.1(6) . . ? C9 C8 C7 123.6(6) . . ? C13 C8 C7 120.2(6) . . ? C8 C9 C10 123.0(8) . . ? C8 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C11 C10 C9 118.4(8) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C12 C11 C10 120.8(8) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 120.1(8) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 121.7(7) . . ? C12 C13 Cl1 118.8(6) . . ? C8 C13 Cl1 119.5(5) . . ? C19 C14 C15 119.9(6) . . ? C19 C14 S1 120.6(5) . . ? C15 C14 S1 119.5(5) . . ? C16 C15 C14 118.8(7) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 122.9(7) . . ? C15 C16 H16 118.6 . . ? C17 C16 H16 118.6 . . ? C18 C17 C16 115.8(7) . . ? C18 C17 C20 123.0(8) . . ? C16 C17 C20 121.1(8) . . ? C17 C18 C19 122.8(7) . . ? C17 C18 H18 118.6 . . ? C19 C18 H18 118.6 . . ? C14 C19 C18 119.8(7) . . ? C14 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 C22 112.3(5) . . ? N2 C21 H21A 109.2 . . ? C22 C21 H21A 109.2 . . ? N2 C21 H21B 109.2 . . ? C22 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C27 C22 C23 119.8(6) . . ? C27 C22 C21 124.2(6) . . ? C23 C22 C21 116.0(6) . . ? C24 C23 C22 123.5(6) . . ? C24 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C23 C24 C26 119.3(7) . . ? C23 C24 C25 121.6(6) . . ? C26 C24 C25 119.1(6) . . ? N2 C25 C24 111.5(5) . . ? N2 C25 H25A 109.3 . . ? C24 C25 H25A 109.3 . . ? N2 C25 H25B 109.3 . . ? C24 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? O6 C26 C24 124.2(8) . . ? O6 C26 H26 117.9 . . ? C24 C26 H26 117.9 . . ? C22 C27 C28 128.0(6) . . ? C22 C27 H27 116.0 . . ? C28 C27 H27 116.0 . . ? C29 C28 C33 116.4(6) . . ? C29 C28 C27 123.4(6) . . ? C33 C28 C27 120.1(6) . . ? C30 C29 C28 122.0(7) . . ? C30 C29 H29 119.0 . . ? C28 C29 H29 119.0 . . ? C31 C30 C29 119.6(8) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C32 C31 C30 120.5(7) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C31 C32 C33 120.5(8) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C32 C33 C28 121.0(7) . . ? C32 C33 Cl2 118.7(6) . . ? C28 C33 Cl2 120.3(6) . . ? C35 C34 C39 119.6(7) . . ? C35 C34 S2 119.5(5) . . ? C39 C34 S2 120.9(6) . . ? C34 C35 C36 120.7(7) . . ? C34 C35 H35 119.6 . . ? C36 C35 H35 119.6 . . ? C37 C36 C35 120.5(8) . . ? C37 C36 H36 119.8 . . ? C35 C36 H36 119.8 . . ? C38 C37 C36 118.1(7) . . ? C38 C37 C40 121.4(8) . . ? C36 C37 C40 120.5(8) . . ? C37 C38 C39 123.2(7) . . ? C37 C38 H38 118.4 . . ? C39 C38 H38 118.4 . . ? C34 C39 C38 117.9(7) . . ? C34 C39 H39 121.0 . . ? C38 C39 H39 121.0 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 N1 C5 -46.8(5) . . . . ? O1 S1 N1 C5 -173.7(4) . . . . ? C14 S1 N1 C5 68.4(5) . . . . ? O2 S1 N1 C1 169.7(4) . . . . ? O1 S1 N1 C1 42.8(5) . . . . ? C14 S1 N1 C1 -75.1(5) . . . . ? O5 S2 N2 C25 48.2(5) . . . . ? O4 S2 N2 C25 175.7(4) . . . . ? C34 S2 N2 C25 -67.3(5) . . . . ? O5 S2 N2 C21 -167.7(4) . . . . ? O4 S2 N2 C21 -40.3(5) . . . . ? C34 S2 N2 C21 76.7(5) . . . . ? C5 N1 C1 C2 -53.2(7) . . . . ? S1 N1 C1 C2 91.9(6) . . . . ? N1 C1 C2 C7 -149.3(6) . . . . ? N1 C1 C2 C3 29.3(7) . . . . ? C7 C2 C3 C4 176.5(6) . . . . ? C1 C2 C3 C4 -2.2(9) . . . . ? C2 C3 C4 C6 178.3(6) . . . . ? C2 C3 C4 C5 -2.4(10) . . . . ? C1 N1 C5 C4 48.0(7) . . . . ? S1 N1 C5 C4 -97.0(6) . . . . ? C3 C4 C5 N1 -20.5(9) . . . . ? C6 C4 C5 N1 158.8(6) . . . . ? C3 C4 C6 O3 178.6(7) . . . . ? C5 C4 C6 O3 -0.6(11) . . . . ? C3 C2 C7 C8 177.5(6) . . . . ? C1 C2 C7 C8 -3.9(10) . . . . ? C2 C7 C8 C9 -45.6(11) . . . . ? C2 C7 C8 C13 137.8(7) . . . . ? C13 C8 C9 C10 -1.2(12) . . . . ? C7 C8 C9 C10 -177.8(8) . . . . ? C8 C9 C10 C11 0.6(15) . . . . ? C9 C10 C11 C12 0.1(16) . . . . ? C10 C11 C12 C13 -0.2(16) . . . . ? C11 C12 C13 C8 -0.4(14) . . . . ? C11 C12 C13 Cl1 -179.2(8) . . . . ? C9 C8 C13 C12 1.1(11) . . . . ? C7 C8 C13 C12 177.9(8) . . . . ? C9 C8 C13 Cl1 179.8(6) . . . . ? C7 C8 C13 Cl1 -3.4(9) . . . . ? O2 S1 C14 C19 26.0(6) . . . . ? O1 S1 C14 C19 155.5(6) . . . . ? N1 S1 C14 C19 -88.6(6) . . . . ? O2 S1 C14 C15 -152.4(6) . . . . ? O1 S1 C14 C15 -22.9(6) . . . . ? N1 S1 C14 C15 93.0(6) . . . . ? C19 C14 C15 C16 -2.9(11) . . . . ? S1 C14 C15 C16 175.5(6) . . . . ? C14 C15 C16 C17 1.3(12) . . . . ? C15 C16 C17 C18 1.3(12) . . . . ? C15 C16 C17 C20 -175.9(8) . . . . ? C16 C17 C18 C19 -2.4(12) . . . . ? C20 C17 C18 C19 174.8(8) . . . . ? C15 C14 C19 C18 1.8(11) . . . . ? S1 C14 C19 C18 -176.5(6) . . . . ? C17 C18 C19 C14 0.9(13) . . . . ? C25 N2 C21 C22 52.7(7) . . . . ? S2 N2 C21 C22 -92.6(6) . . . . ? N2 C21 C22 C27 153.4(6) . . . . ? N2 C21 C22 C23 -28.7(7) . . . . ? C27 C22 C23 C24 -179.7(6) . . . . ? C21 C22 C23 C24 2.3(9) . . . . ? C22 C23 C24 C26 -178.3(6) . . . . ? C22 C23 C24 C25 1.5(10) . . . . ? C21 N2 C25 C24 -48.4(7) . . . . ? S2 N2 C25 C24 97.4(6) . . . . ? C23 C24 C25 N2 21.6(8) . . . . ? C26 C24 C25 N2 -158.7(6) . . . . ? C23 C24 C26 O6 176.5(8) . . . . ? C25 C24 C26 O6 -3.2(12) . . . . ? C23 C22 C27 C28 -177.2(6) . . . . ? C21 C22 C27 C28 0.6(10) . . . . ? C22 C27 C28 C29 41.2(10) . . . . ? C22 C27 C28 C33 -141.9(7) . . . . ? C33 C28 C29 C30 -0.8(11) . . . . ? C27 C28 C29 C30 176.2(7) . . . . ? C28 C29 C30 C31 0.1(13) . . . . ? C29 C30 C31 C32 0.4(13) . . . . ? C30 C31 C32 C33 -0.2(13) . . . . ? C31 C32 C33 C28 -0.5(12) . . . . ? C31 C32 C33 Cl2 179.4(7) . . . . ? C29 C28 C33 C32 1.0(10) . . . . ? C27 C28 C33 C32 -176.1(7) . . . . ? C29 C28 C33 Cl2 -178.9(6) . . . . ? C27 C28 C33 Cl2 4.0(9) . . . . ? O5 S2 C34 C35 156.4(6) . . . . ? O4 S2 C34 C35 26.8(7) . . . . ? N2 S2 C34 C35 -88.4(6) . . . . ? O5 S2 C34 C39 -24.1(7) . . . . ? O4 S2 C34 C39 -153.6(6) . . . . ? N2 S2 C34 C39 91.1(6) . . . . ? C39 C34 C35 C36 1.2(12) . . . . ? S2 C34 C35 C36 -179.3(6) . . . . ? C34 C35 C36 C37 0.4(12) . . . . ? C35 C36 C37 C38 -2.2(12) . . . . ? C35 C36 C37 C40 178.1(8) . . . . ? C36 C37 C38 C39 2.6(13) . . . . ? C40 C37 C38 C39 -177.7(8) . . . . ? C35 C34 C39 C38 -0.9(11) . . . . ? S2 C34 C39 C38 179.6(6) . . . . ? C37 C38 C39 C34 -1.1(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C18 H18 O6 0.93 2.47 3.227(10) 138.1 4_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.627 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.096