data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Min Shi' _publ_contact_author_address ; State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry 354 Fenglin Lu Shanghai 200032 CHINA ; _publ_contact_author_email MSHI@MAIL.SIOC.AC.CN _publ_section_title ; Baylis-Hillman Reactions of N-Tosyl Aldimines and Aryl Aldehydes with 3-Methylpenta-3,4-dien-2-one ; loop_ _publ_author_name 'Min Shi' 'Gui-Ling Zhao' data_cd2509 _database_code_depnum_ccdc_archive 'CCDC 266290' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 Cl2 N O3 S' _chemical_formula_weight 424.32 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 8.7617(12) _cell_length_b 12.4255(16) _cell_length_c 37.845(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.123(3) _cell_angle_gamma 90.00 _cell_volume 4109.5(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2353 _cell_measurement_theta_min 5.699 _cell_measurement_theta_max 41.403 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.510 _exptl_crystal_size_mid 0.495 _exptl_crystal_size_min 0.107 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.437 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.64261 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _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 21081 _diffrn_reflns_av_R_equivalents 0.0938 _diffrn_reflns_av_sigmaI/netI 0.1164 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7614 _reflns_number_gt 3788 _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^)+(0.0709P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7614 _refine_ls_number_parameters 493 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1297 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.1770 _refine_ls_wR_factor_gt 0.1469 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _refine_ls_shift/su_max 0.006 _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 0.00296(17) 0.31633(10) 0.35270(4) 0.0558(4) Uani 1 1 d . . . S2 S 0.43955(15) 0.31395(9) 0.14305(3) 0.0524(4) Uani 1 1 d . . . Cl1 Cl 0.32912(18) 0.50279(12) 0.43569(3) 0.0731(4) Uani 1 1 d . . . Cl2 Cl 0.2086(3) 0.71443(13) 0.46818(4) 0.1086(7) Uani 1 1 d . . . Cl3 Cl 0.69963(19) 0.50171(12) 0.05834(3) 0.0777(5) Uani 1 1 d . . . Cl4 Cl 0.5567(3) 0.71717(14) 0.02784(4) 0.1107(7) Uani 1 1 d . . . N1 N 0.1131(4) 0.4033(3) 0.33515(9) 0.0441(10) Uani 1 1 d . . . H1 H 0.1035 0.4160 0.3128 0.053 Uiso 1 1 calc R . . N2 N 0.5633(4) 0.4013(3) 0.16036(9) 0.0432(10) Uani 1 1 d . . . H2 H 0.5695 0.4140 0.1828 0.052 Uiso 1 1 calc R . . O1 O 0.4045(5) 0.5194(3) 0.21501(10) 0.0878(14) Uani 1 1 d . . . O2 O -0.1075(5) 0.2874(3) 0.32505(9) 0.0823(12) Uani 1 1 d . . . O3 O 0.0972(5) 0.2355(2) 0.36997(10) 0.0793(12) Uani 1 1 d . . . O4 O 0.9210(5) 0.5212(3) 0.28021(10) 0.0891(13) Uani 1 1 d . . . O5 O 0.3493(4) 0.2823(3) 0.17129(9) 0.0733(11) Uani 1 1 d . . . O6 O 0.5214(4) 0.2350(2) 0.12433(10) 0.0741(11) Uani 1 1 d . . . C1 C 0.3666(6) 0.5302(4) 0.24491(14) 0.0602(15) Uani 1 1 d . . . C2 C 0.4175(6) 0.4527(4) 0.27238(13) 0.0510(13) Uani 1 1 d . . . C3 C 0.3872(5) 0.4707(3) 0.30533(13) 0.0478(12) Uani 1 1 d . . . C4 C 0.3651(5) 0.4922(4) 0.33789(12) 0.0487(12) Uani 1 1 d . . . H4 H 0.4411 0.5319 0.3504 0.058 Uiso 1 1 calc R . . C5 C 0.2294(5) 0.4602(3) 0.35794(11) 0.0401(11) Uani 1 1 d . . . H5 H 0.2655 0.4114 0.3771 0.048 Uiso 1 1 calc R . . C6 C 0.1675(5) 0.5622(3) 0.37466(11) 0.0390(11) Uani 1 1 d . . . C7 C 0.2102(5) 0.5870(3) 0.40962(11) 0.0436(12) Uani 1 1 d . . . C8 C 0.1559(6) 0.6833(4) 0.42399(12) 0.0556(14) Uani 1 1 d . . . C9 C 0.0637(6) 0.7520(4) 0.40414(14) 0.0570(14) Uani 1 1 d . . . H9 H 0.0273 0.8147 0.4140 0.068 Uiso 1 1 calc R . . C10 C 0.0255(6) 0.7271(4) 0.36920(13) 0.0537(13) Uani 1 1 d . . . H10 H -0.0368 0.7734 0.3553 0.064 Uiso 1 1 calc R . . C11 C 0.0786(5) 0.6346(3) 0.35489(11) 0.0454(12) Uani 1 1 d . . . H11 H 0.0540 0.6202 0.3311 0.054 Uiso 1 1 calc R . . C12 C 0.2698(7) 0.6249(4) 0.25399(15) 0.0780(18) Uani 1 1 d . . . H12A H 0.3260 0.6692 0.2712 0.117 Uiso 1 1 calc R . . H12B H 0.1779 0.5996 0.2636 0.117 Uiso 1 1 calc R . . H12C H 0.2438 0.6662 0.2330 0.117 Uiso 1 1 calc R . . C13 C 0.5107(6) 0.3565(4) 0.26210(13) 0.0660(16) Uani 1 1 d . . . H13A H 0.6070 0.3806 0.2544 0.099 Uiso 1 1 calc R . . H13B H 0.4558 0.3181 0.2432 0.099 Uiso 1 1 calc R . . H13C H 0.5284 0.3098 0.2822 0.099 Uiso 1 1 calc R . . C14 C -0.0862(5) 0.3871(3) 0.38562(12) 0.0439(12) Uani 1 1 d . . . C15 C -0.0401(6) 0.3693(4) 0.42086(13) 0.0550(13) Uani 1 1 d . . . H15 H 0.0309 0.3159 0.4272 0.066 Uiso 1 1 calc R . . C16 C -0.1015(6) 0.4326(4) 0.44655(13) 0.0576(14) Uani 1 1 d . . . H16 H -0.0706 0.4210 0.4703 0.069 Uiso 1 1 calc R . . C17 C -0.2066(6) 0.5119(4) 0.43780(13) 0.0538(13) Uani 1 1 d . . . C18 C -0.2542(6) 0.5259(4) 0.40244(13) 0.0532(13) Uani 1 1 d . . . H18 H -0.3272 0.5780 0.3961 0.064 Uiso 1 1 calc R . . C19 C -0.1947(6) 0.4636(4) 0.37646(12) 0.0477(12) Uani 1 1 d . . . H19 H -0.2282 0.4736 0.3528 0.057 Uiso 1 1 calc R . . C20 C -0.2660(7) 0.5841(5) 0.46622(14) 0.0835(19) Uani 1 1 d . . . H20A H -0.2423 0.5525 0.4891 0.125 Uiso 1 1 calc R . . H20B H -0.3749 0.5919 0.4622 0.125 Uiso 1 1 calc R . . H20C H -0.2185 0.6536 0.4653 0.125 Uiso 1 1 calc R . . C21 C 0.8687(7) 0.5339(4) 0.24980(16) 0.0673(16) Uani 1 1 d . . . C22 C 0.9025(6) 0.4540(4) 0.22316(14) 0.0548(13) Uani 1 1 d . . . C23 C 0.8521(6) 0.4713(4) 0.18992(14) 0.0500(13) Uani 1 1 d . . . C24 C 0.8106(6) 0.4895(4) 0.15706(13) 0.0497(12) Uani 1 1 d . . . H24 H 0.8801 0.5269 0.1442 0.060 Uiso 1 1 calc R . . C25 C 0.6633(5) 0.4575(3) 0.13705(11) 0.0405(11) Uani 1 1 d . . . H25 H 0.6867 0.4088 0.1178 0.049 Uiso 1 1 calc R . . C26 C 0.5912(5) 0.5612(3) 0.12079(11) 0.0399(11) Uani 1 1 d . . . C27 C 0.6051(5) 0.5876(3) 0.08564(11) 0.0446(12) Uani 1 1 d . . . C28 C 0.5426(6) 0.6835(4) 0.07212(12) 0.0578(14) Uani 1 1 d . . . C29 C 0.4668(6) 0.7530(4) 0.09284(14) 0.0566(14) Uani 1 1 d . . . H29 H 0.4235 0.8159 0.0833 0.068 Uiso 1 1 calc R . . C30 C 0.4557(6) 0.7277(4) 0.12831(14) 0.0556(14) Uani 1 1 d . . . H30 H 0.4053 0.7740 0.1429 0.067 Uiso 1 1 calc R . . C31 C 0.5196(5) 0.6339(3) 0.14172(11) 0.0447(12) Uani 1 1 d . . . H31 H 0.5145 0.6189 0.1657 0.054 Uiso 1 1 calc R . . C32 C 0.7711(7) 0.6294(4) 0.23992(16) 0.087(2) Uani 1 1 d . . . H32A H 0.7392 0.6630 0.2610 0.131 Uiso 1 1 calc R . . H32B H 0.6827 0.6066 0.2254 0.131 Uiso 1 1 calc R . . H32C H 0.8287 0.6798 0.2270 0.131 Uiso 1 1 calc R . . C33 C 0.9967(7) 0.3573(4) 0.23486(13) 0.0683(16) Uani 1 1 d . . . H33A H 0.9997 0.3076 0.2155 0.102 Uiso 1 1 calc R . . H33B H 0.9516 0.3228 0.2543 0.102 Uiso 1 1 calc R . . H33C H 1.0988 0.3798 0.2422 0.102 Uiso 1 1 calc R . . C34 C 0.3245(5) 0.3856(3) 0.11142(11) 0.0411(11) Uani 1 1 d . . . C35 C 0.3438(6) 0.3710(4) 0.07582(13) 0.0546(13) Uani 1 1 d . . . H35 H 0.4076 0.3170 0.0683 0.066 Uiso 1 1 calc R . . C36 C 0.2656(7) 0.4387(4) 0.05132(13) 0.0607(15) Uani 1 1 d . . . H36 H 0.2776 0.4283 0.0273 0.073 Uiso 1 1 calc R . . C37 C 0.1719(6) 0.5199(4) 0.06118(13) 0.0532(13) Uani 1 1 d . . . C38 C 0.1528(6) 0.5312(4) 0.09710(13) 0.0494(12) Uani 1 1 d . . . H38 H 0.0871 0.5841 0.1044 0.059 Uiso 1 1 calc R . . C39 C 0.2284(5) 0.4660(4) 0.12228(12) 0.0480(12) Uani 1 1 d . . . H39 H 0.2150 0.4759 0.1462 0.058 Uiso 1 1 calc R . . C40 C 0.0988(7) 0.5980(4) 0.03448(14) 0.0776(18) Uani 1 1 d . . . H40A H 0.1660 0.6580 0.0319 0.116 Uiso 1 1 calc R . . H40B H 0.0036 0.6230 0.0425 0.116 Uiso 1 1 calc R . . H40C H 0.0803 0.5625 0.0120 0.116 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 0.0714(10) 0.0340(7) 0.0648(9) -0.0097(7) 0.0245(7) -0.0094(7) S2 0.0604(9) 0.0335(7) 0.0616(8) 0.0075(6) -0.0062(7) -0.0078(6) Cl1 0.0956(11) 0.0749(9) 0.0456(7) -0.0009(7) -0.0157(7) 0.0151(9) Cl2 0.195(2) 0.0809(11) 0.0484(9) -0.0299(8) -0.0018(10) 0.0008(12) Cl3 0.1100(13) 0.0745(9) 0.0524(8) 0.0092(7) 0.0317(8) 0.0270(9) Cl4 0.181(2) 0.0986(13) 0.0545(9) 0.0375(9) 0.0219(11) 0.0329(13) N1 0.057(3) 0.045(2) 0.032(2) -0.0100(17) 0.0119(18) -0.011(2) N2 0.054(3) 0.040(2) 0.035(2) 0.0052(17) -0.0018(18) -0.0121(19) O1 0.116(4) 0.091(3) 0.062(2) 0.017(2) 0.045(2) 0.013(3) O2 0.093(3) 0.078(3) 0.077(3) -0.041(2) 0.014(2) -0.043(2) O3 0.108(3) 0.0298(18) 0.105(3) 0.0130(19) 0.043(3) 0.014(2) O4 0.104(4) 0.092(3) 0.067(3) -0.015(2) -0.025(2) 0.005(3) O5 0.073(3) 0.072(2) 0.074(2) 0.038(2) 0.001(2) -0.026(2) O6 0.089(3) 0.0325(18) 0.097(3) -0.0113(19) -0.015(2) 0.0097(19) C1 0.068(4) 0.051(3) 0.065(4) 0.002(3) 0.028(3) -0.008(3) C2 0.058(3) 0.041(3) 0.057(3) -0.004(2) 0.023(3) -0.003(3) C3 0.047(3) 0.045(3) 0.053(3) -0.009(2) 0.016(2) -0.006(2) C4 0.045(3) 0.049(3) 0.053(3) -0.011(2) 0.008(2) -0.003(2) C5 0.050(3) 0.037(3) 0.033(2) -0.005(2) 0.001(2) 0.002(2) C6 0.047(3) 0.036(2) 0.034(2) -0.004(2) 0.009(2) -0.007(2) C7 0.058(3) 0.036(3) 0.037(3) 0.002(2) 0.005(2) -0.004(2) C8 0.082(4) 0.047(3) 0.039(3) -0.010(2) 0.015(3) -0.016(3) C9 0.073(4) 0.030(3) 0.069(4) -0.008(3) 0.016(3) -0.003(3) C10 0.061(4) 0.043(3) 0.058(3) 0.002(3) 0.007(3) 0.007(3) C11 0.057(3) 0.042(3) 0.037(3) -0.001(2) 0.003(2) 0.005(3) C12 0.086(4) 0.048(3) 0.105(5) 0.017(3) 0.041(4) 0.011(3) C13 0.082(4) 0.047(3) 0.073(4) -0.007(3) 0.033(3) 0.005(3) C14 0.049(3) 0.037(3) 0.046(3) 0.002(2) 0.011(2) -0.012(2) C15 0.060(4) 0.039(3) 0.067(4) 0.013(3) 0.012(3) 0.005(3) C16 0.072(4) 0.060(3) 0.041(3) 0.008(3) 0.003(3) -0.001(3) C17 0.062(4) 0.047(3) 0.053(3) -0.002(3) 0.015(3) 0.002(3) C18 0.057(3) 0.046(3) 0.056(3) 0.005(3) 0.005(3) 0.000(3) C19 0.054(3) 0.046(3) 0.043(3) 0.008(2) 0.000(2) -0.002(3) C20 0.097(5) 0.089(4) 0.066(4) -0.022(3) 0.019(3) 0.003(4) C21 0.069(4) 0.056(3) 0.075(4) -0.012(3) -0.013(3) -0.013(3) C22 0.052(3) 0.046(3) 0.065(4) 0.006(3) -0.002(3) -0.007(3) C23 0.047(3) 0.040(3) 0.062(3) 0.010(3) -0.002(3) -0.010(2) C24 0.046(3) 0.041(3) 0.062(3) 0.017(3) 0.006(3) 0.000(2) C25 0.055(3) 0.033(2) 0.033(2) 0.004(2) 0.002(2) 0.003(2) C26 0.043(3) 0.036(2) 0.040(3) 0.004(2) 0.003(2) -0.008(2) C27 0.056(3) 0.041(3) 0.037(3) 0.005(2) 0.002(2) 0.001(2) C28 0.072(4) 0.055(3) 0.047(3) 0.021(3) 0.007(3) -0.004(3) C29 0.069(4) 0.033(3) 0.068(4) 0.010(3) 0.003(3) 0.004(3) C30 0.064(4) 0.036(3) 0.067(3) 0.001(3) 0.006(3) -0.003(3) C31 0.060(3) 0.035(3) 0.040(3) 0.002(2) 0.007(2) 0.008(2) C32 0.091(5) 0.045(3) 0.120(5) -0.025(3) -0.036(4) 0.010(3) C33 0.090(4) 0.040(3) 0.072(4) 0.007(3) -0.018(3) 0.013(3) C34 0.049(3) 0.033(2) 0.041(3) 0.000(2) 0.001(2) -0.009(2) C35 0.065(4) 0.042(3) 0.057(3) -0.010(3) 0.005(3) 0.000(3) C36 0.088(4) 0.056(3) 0.038(3) -0.003(3) 0.006(3) 0.002(3) C37 0.063(4) 0.038(3) 0.057(3) 0.008(2) -0.002(3) -0.007(3) C38 0.050(3) 0.040(3) 0.059(3) -0.001(2) 0.008(3) 0.002(2) C39 0.052(3) 0.049(3) 0.044(3) -0.006(2) 0.011(2) -0.005(3) C40 0.099(5) 0.057(3) 0.074(4) 0.014(3) -0.014(3) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.419(4) . ? S1 O3 1.428(4) . ? S1 N1 1.623(4) . ? S1 C14 1.754(5) . ? S2 O5 1.429(3) . ? S2 O6 1.433(4) . ? S2 N2 1.638(4) . ? S2 C34 1.752(5) . ? Cl1 C7 1.734(5) . ? Cl2 C8 1.746(5) . ? Cl3 C27 1.737(5) . ? Cl4 C28 1.740(5) . ? N1 C5 1.468(5) . ? N1 H1 0.8600 . ? N2 C25 1.464(5) . ? N2 H2 0.8600 . ? O1 C1 1.210(5) . ? O4 C21 1.218(6) . ? C1 C2 1.463(7) . ? C1 C12 1.504(7) . ? C2 C3 1.313(6) . ? C2 C13 1.514(6) . ? C3 C4 1.289(6) . ? C4 C5 1.510(6) . ? C4 H4 0.9300 . ? C5 C6 1.533(6) . ? C5 H5 0.9800 . ? C6 C11 1.375(6) . ? C6 C7 1.383(6) . ? C7 C8 1.411(6) . ? C8 C9 1.364(7) . ? C9 C10 1.376(6) . ? C9 H9 0.9300 . ? C10 C11 1.366(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C19 1.372(6) . ? C14 C15 1.383(6) . ? C15 C16 1.389(6) . ? C15 H15 0.9300 . ? C16 C17 1.373(7) . ? C16 H16 0.9300 . ? C17 C18 1.384(6) . ? C17 C20 1.521(6) . ? C18 C19 1.382(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.461(7) . ? C21 C32 1.494(7) . ? C22 C23 1.320(6) . ? C22 C33 1.506(6) . ? C23 C24 1.290(6) . ? C24 C25 1.503(6) . ? C24 H24 0.9300 . ? C25 C26 1.543(6) . ? C25 H25 0.9800 . ? C26 C31 1.382(6) . ? C26 C27 1.384(5) . ? C27 C28 1.392(6) . ? C28 C29 1.370(6) . ? C29 C30 1.389(6) . ? C29 H29 0.9300 . ? C30 C31 1.375(6) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C35 1.382(6) . ? C34 C39 1.388(6) . ? C35 C36 1.395(7) . ? C35 H35 0.9300 . ? C36 C37 1.370(7) . ? C36 H36 0.9300 . ? C37 C38 1.388(6) . ? C37 C40 1.509(6) . ? C38 C39 1.382(6) . ? 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 O3 120.0(2) . . ? O2 S1 N1 105.1(2) . . ? O3 S1 N1 108.3(2) . . ? O2 S1 C14 109.6(2) . . ? O3 S1 C14 107.4(2) . . ? N1 S1 C14 105.39(19) . . ? O5 S2 O6 120.3(2) . . ? O5 S2 N2 105.6(2) . . ? O6 S2 N2 108.1(2) . . ? O5 S2 C34 109.2(2) . . ? O6 S2 C34 107.1(2) . . ? N2 S2 C34 105.56(19) . . ? C5 N1 S1 119.2(3) . . ? C5 N1 H1 120.4 . . ? S1 N1 H1 120.4 . . ? C25 N2 S2 118.8(3) . . ? C25 N2 H2 120.6 . . ? S2 N2 H2 120.6 . . ? O1 C1 C2 120.0(5) . . ? O1 C1 C12 119.9(5) . . ? C2 C1 C12 120.1(5) . . ? C3 C2 C1 119.4(4) . . ? C3 C2 C13 121.9(5) . . ? C1 C2 C13 118.7(4) . . ? C4 C3 C2 176.3(5) . . ? C3 C4 C5 127.1(4) . . ? C3 C4 H4 116.4 . . ? C5 C4 H4 116.4 . . ? N1 C5 C4 111.7(3) . . ? N1 C5 C6 112.9(4) . . ? C4 C5 C6 107.7(3) . . ? N1 C5 H5 108.1 . . ? C4 C5 H5 108.1 . . ? C6 C5 H5 108.1 . . ? C11 C6 C7 118.6(4) . . ? C11 C6 C5 121.3(4) . . ? C7 C6 C5 120.0(4) . . ? C6 C7 C8 118.8(4) . . ? C6 C7 Cl1 121.3(3) . . ? C8 C7 Cl1 119.9(4) . . ? C9 C8 C7 121.4(4) . . ? C9 C8 Cl2 119.6(4) . . ? C7 C8 Cl2 118.9(4) . . ? C8 C9 C10 118.8(4) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 120.3(5) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C6 122.0(4) . . ? C10 C11 H11 119.0 . . ? C6 C11 H11 119.0 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 120.2(4) . . ? C19 C14 S1 120.3(4) . . ? C15 C14 S1 119.4(4) . . ? C14 C15 C16 118.9(5) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C17 C16 C15 121.6(5) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 118.3(4) . . ? C16 C17 C20 120.7(5) . . ? C18 C17 C20 121.0(5) . . ? C19 C18 C17 121.0(5) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C14 C19 C18 119.9(4) . . ? 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 . . ? O4 C21 C22 118.9(5) . . ? O4 C21 C32 120.6(5) . . ? C22 C21 C32 120.5(5) . . ? C23 C22 C21 118.4(5) . . ? C23 C22 C33 123.3(5) . . ? C21 C22 C33 118.3(5) . . ? C24 C23 C22 176.8(5) . . ? C23 C24 C25 127.7(4) . . ? C23 C24 H24 116.1 . . ? C25 C24 H24 116.1 . . ? N2 C25 C24 110.6(3) . . ? N2 C25 C26 113.1(4) . . ? C24 C25 C26 106.9(3) . . ? N2 C25 H25 108.7 . . ? C24 C25 H25 108.7 . . ? C26 C25 H25 108.7 . . ? C31 C26 C27 118.1(4) . . ? C31 C26 C25 120.5(4) . . ? C27 C26 C25 121.3(4) . . ? C26 C27 C28 119.8(4) . . ? C26 C27 Cl3 120.3(3) . . ? C28 C27 Cl3 119.9(3) . . ? C29 C28 C27 121.5(4) . . ? C29 C28 Cl4 118.1(4) . . ? C27 C28 Cl4 120.4(4) . . ? C28 C29 C30 118.8(5) . . ? C28 C29 H29 120.6 . . ? C30 C29 H29 120.6 . . ? C31 C30 C29 119.6(5) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C30 C31 C26 122.2(4) . . ? C30 C31 H31 118.9 . . ? C26 C31 H31 118.9 . . ? C21 C32 H32A 109.5 . . ? C21 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C21 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C22 C33 H33A 109.5 . . ? C22 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C22 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C39 120.2(4) . . ? C35 C34 S2 119.6(4) . . ? C39 C34 S2 119.7(4) . . ? C34 C35 C36 118.7(5) . . ? C34 C35 H35 120.7 . . ? C36 C35 H35 120.7 . . ? C37 C36 C35 122.6(5) . . ? C37 C36 H36 118.7 . . ? C35 C36 H36 118.7 . . ? C36 C37 C38 117.2(5) . . ? C36 C37 C40 121.6(5) . . ? C38 C37 C40 121.1(5) . . ? C39 C38 C37 122.0(4) . . ? C39 C38 H38 119.0 . . ? C37 C38 H38 119.0 . . ? C38 C39 C34 119.2(4) . . ? C38 C39 H39 120.4 . . ? C34 C39 H39 120.4 . . ? 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 172.4(3) . . . . ? O3 S1 N1 C5 -58.1(4) . . . . ? C14 S1 N1 C5 56.7(4) . . . . ? O5 S2 N2 C25 -173.9(3) . . . . ? O6 S2 N2 C25 56.1(4) . . . . ? C34 S2 N2 C25 -58.3(4) . . . . ? O1 C1 C2 C3 173.9(5) . . . . ? C12 C1 C2 C3 -4.8(7) . . . . ? O1 C1 C2 C13 -3.2(8) . . . . ? C12 C1 C2 C13 178.2(5) . . . . ? C1 C2 C3 C4 -83(8) . . . . ? C13 C2 C3 C4 94(8) . . . . ? C2 C3 C4 C5 173(8) . . . . ? S1 N1 C5 C4 151.7(3) . . . . ? S1 N1 C5 C6 -86.7(4) . . . . ? C3 C4 C5 N1 -3.2(7) . . . . ? C3 C4 C5 C6 -127.7(5) . . . . ? N1 C5 C6 C11 -45.7(5) . . . . ? C4 C5 C6 C11 78.1(5) . . . . ? N1 C5 C6 C7 139.1(4) . . . . ? C4 C5 C6 C7 -97.1(5) . . . . ? C11 C6 C7 C8 2.5(6) . . . . ? C5 C6 C7 C8 177.8(4) . . . . ? C11 C6 C7 Cl1 -177.1(3) . . . . ? C5 C6 C7 Cl1 -1.8(6) . . . . ? C6 C7 C8 C9 -0.4(7) . . . . ? Cl1 C7 C8 C9 179.2(4) . . . . ? C6 C7 C8 Cl2 179.6(3) . . . . ? Cl1 C7 C8 Cl2 -0.7(6) . . . . ? C7 C8 C9 C10 -1.1(7) . . . . ? Cl2 C8 C9 C10 178.9(4) . . . . ? C8 C9 C10 C11 0.4(7) . . . . ? C9 C10 C11 C6 1.8(7) . . . . ? C7 C6 C11 C10 -3.3(7) . . . . ? C5 C6 C11 C10 -178.5(4) . . . . ? O2 S1 C14 C19 -42.1(4) . . . . ? O3 S1 C14 C19 -174.1(4) . . . . ? N1 S1 C14 C19 70.5(4) . . . . ? O2 S1 C14 C15 141.5(4) . . . . ? O3 S1 C14 C15 9.5(4) . . . . ? N1 S1 C14 C15 -105.8(4) . . . . ? C19 C14 C15 C16 -2.2(7) . . . . ? S1 C14 C15 C16 174.2(4) . . . . ? C14 C15 C16 C17 0.1(7) . . . . ? C15 C16 C17 C18 1.8(8) . . . . ? C15 C16 C17 C20 -176.8(5) . . . . ? C16 C17 C18 C19 -1.6(7) . . . . ? C20 C17 C18 C19 176.9(5) . . . . ? C15 C14 C19 C18 2.3(7) . . . . ? S1 C14 C19 C18 -174.0(4) . . . . ? C17 C18 C19 C14 -0.4(7) . . . . ? O4 C21 C22 C23 -176.4(5) . . . . ? C32 C21 C22 C23 3.8(8) . . . . ? O4 C21 C22 C33 1.9(8) . . . . ? C32 C21 C22 C33 -177.8(5) . . . . ? C21 C22 C23 C24 106(9) . . . . ? C33 C22 C23 C24 -72(9) . . . . ? C22 C23 C24 C25 164(9) . . . . ? S2 N2 C25 C24 -152.6(3) . . . . ? S2 N2 C25 C26 87.5(4) . . . . ? C23 C24 C25 N2 1.1(7) . . . . ? C23 C24 C25 C26 124.7(5) . . . . ? N2 C25 C26 C31 46.2(5) . . . . ? C24 C25 C26 C31 -75.9(5) . . . . ? N2 C25 C26 C27 -138.2(4) . . . . ? C24 C25 C26 C27 99.7(5) . . . . ? C31 C26 C27 C28 -2.3(7) . . . . ? C25 C26 C27 C28 -178.0(4) . . . . ? C31 C26 C27 Cl3 177.8(4) . . . . ? C25 C26 C27 Cl3 2.1(6) . . . . ? C26 C27 C28 C29 -0.1(7) . . . . ? Cl3 C27 C28 C29 179.7(4) . . . . ? C26 C27 C28 Cl4 -179.1(4) . . . . ? Cl3 C27 C28 Cl4 0.7(6) . . . . ? C27 C28 C29 C30 1.5(8) . . . . ? Cl4 C28 C29 C30 -179.4(4) . . . . ? C28 C29 C30 C31 -0.5(7) . . . . ? C29 C30 C31 C26 -2.1(7) . . . . ? C27 C26 C31 C30 3.5(7) . . . . ? C25 C26 C31 C30 179.2(4) . . . . ? O5 S2 C34 C35 -141.6(4) . . . . ? O6 S2 C34 C35 -9.8(4) . . . . ? N2 S2 C34 C35 105.3(4) . . . . ? O5 S2 C34 C39 46.4(4) . . . . ? O6 S2 C34 C39 178.2(3) . . . . ? N2 S2 C34 C39 -66.8(4) . . . . ? C39 C34 C35 C36 0.3(7) . . . . ? S2 C34 C35 C36 -171.7(4) . . . . ? C34 C35 C36 C37 0.8(8) . . . . ? C35 C36 C37 C38 -1.9(8) . . . . ? C35 C36 C37 C40 174.9(5) . . . . ? C36 C37 C38 C39 2.1(7) . . . . ? C40 C37 C38 C39 -174.7(5) . . . . ? C37 C38 C39 C34 -1.1(7) . . . . ? C35 C34 C39 C38 -0.2(7) . . . . ? S2 C34 C39 C38 171.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.335 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.061