# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1225yu _database_code_depnum_ccdc_archive 'CCDC 924230' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cl N O3 S' _chemical_formula_weight 309.76 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4413(2) _cell_length_b 15.6524(3) _cell_length_c 9.8374(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.5778(14) _cell_angle_gamma 90.00 _cell_volume 1322.05(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7203 _cell_measurement_theta_min 4.94 _cell_measurement_theta_max 68.24 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 4.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4941 _exptl_absorpt_correction_T_max 0.8211 _exptl_absorpt_process_details ;Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7504 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.1017 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.94 _diffrn_reflns_theta_max 63.00 _reflns_number_total 3777 _reflns_number_gt 3242 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 3777 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.7068(7) 0.9146(3) -0.1457(6) 0.0205(13) Uani 1 1 d . . . N1 N 0.8427(6) 0.9577(3) -0.0316(5) 0.0218(11) Uani 1 1 d . . . H31 H 0.9126 0.9876 -0.0487 0.026 Uiso 1 1 calc R . . S1 S 0.84232(18) 0.94075(9) 0.13226(16) 0.0248(3) Uani 1 1 d . . . O1 O 0.7506(6) 0.8529(3) 0.0927(5) 0.0412(13) Uani 1 1 d . . . C3 C 0.6935(8) 0.8314(4) -0.0639(6) 0.0282(15) Uani 1 1 d . . . H32 H 0.5838 0.8122 -0.1028 0.034 Uiso 1 1 calc R . . H33 H 0.7569 0.7851 -0.0790 0.034 Uiso 1 1 calc R . . O2 O 0.7414(5) 0.9998(3) 0.1600(5) 0.0332(11) Uani 1 1 d . . . O3 O 0.9941(5) 0.9292(3) 0.2439(4) 0.0281(10) Uani 1 1 d . . . C4 C 0.5615(7) 0.9721(4) -0.1948(7) 0.0263(14) Uani 1 1 d . . . C5 C 0.4165(7) 0.9373(4) -0.2808(6) 0.0252(13) Uani 1 1 d . . . H5 H 0.4079 0.8780 -0.3031 0.030 Uiso 1 1 calc R . . C6 C 0.2843(7) 0.9877(3) -0.3346(7) 0.0265(14) Uani 1 1 d . . . H6 H 0.1853 0.9633 -0.3926 0.032 Uiso 1 1 calc R . . C7 C 0.2982(8) 1.0741(3) -0.3030(7) 0.0274(15) Uani 1 1 d . . . C8 C 0.4396(7) 1.1111(4) -0.2207(7) 0.0273(15) Uani 1 1 d . . . H8 H 0.4478 1.1708 -0.2010 0.033 Uiso 1 1 calc R . . C9 C 0.5722(7) 1.0586(4) -0.1661(6) 0.0212(13) Uani 1 1 d . . . H9 H 0.6712 1.0831 -0.1083 0.025 Uiso 1 1 calc R . . C10 C 0.7369(7) 0.8938(4) -0.2826(7) 0.0253(13) Uani 1 1 d . . . C11 C 0.6749(7) 0.8190(3) -0.3625(7) 0.0277(15) Uani 1 1 d . . . H11 H 0.6205 0.7802 -0.3271 0.033 Uiso 1 1 calc R . . C12 C 0.6916(7) 0.8006(4) -0.4912(7) 0.0298(15) Uani 1 1 d . . . H12 H 0.6506 0.7489 -0.5433 0.036 Uiso 1 1 calc R . . C13 C 0.7685(7) 0.8576(4) -0.5454(7) 0.0316(15) Uani 1 1 d . . . H13 H 0.7794 0.8451 -0.6351 0.038 Uiso 1 1 calc R . . C14 C 0.8293(8) 0.9326(4) -0.4689(7) 0.0316(15) Uani 1 1 d . . . H14 H 0.8809 0.9720 -0.5063 0.038 Uiso 1 1 calc R . . C15 C 0.8140(7) 0.9500(3) -0.3359(7) 0.0252(13) Uani 1 1 d . . . H15 H 0.8573 1.0009 -0.2822 0.030 Uiso 1 1 calc R . . C16 C -0.6350(7) 1.0283(3) -0.7877(6) 0.0205(13) Uani 1 1 d . . . N2 N -0.6036(6) 0.9860(3) -0.9080(5) 0.0262(12) Uani 1 1 d . . . H34 H -0.5452 1.0067 -0.9504 0.031 Uiso 1 1 calc R . . S2 S -0.69624(18) 0.89442(9) -0.94827(17) 0.0262(4) Uani 1 1 d . . . O4 O -0.7051(5) 0.8789(2) -0.7941(5) 0.0319(11) Uani 1 1 d . . . C18 C -0.6445(8) 0.9508(3) -0.6915(7) 0.0275(14) Uani 1 1 d . . . H35 H -0.5400 0.9371 -0.6131 0.033 Uiso 1 1 calc R . . H36 H -0.7148 0.9641 -0.6426 0.033 Uiso 1 1 calc R . . O5 O -0.6032(5) 0.8300(2) -0.9724(5) 0.0351(11) Uani 1 1 d . . . O6 O -0.8528(5) 0.9046(3) -1.0568(5) 0.0359(11) Uani 1 1 d . . . C19 C -0.5057(7) 1.0891(3) -0.7006(7) 0.0231(13) Uani 1 1 d . . . C20 C -0.4386(7) 1.1416(4) -0.7747(7) 0.0244(13) Uani 1 1 d . . . H20 H -0.4702 1.1352 -0.8793 0.029 Uiso 1 1 calc R . . C21 C -0.3298(7) 1.2011(3) -0.6992(7) 0.0260(14) Uani 1 1 d . . . H21 H -0.2845 1.2353 -0.7503 0.031 Uiso 1 1 calc R . . C22 C -0.2852(7) 1.2115(4) -0.5479(7) 0.0279(15) Uani 1 1 d . . . C23 C -0.3517(7) 1.1618(4) -0.4730(7) 0.0276(14) Uani 1 1 d . . . H23 H -0.3213 1.1697 -0.3689 0.033 Uiso 1 1 calc R . . C24 C -0.4609(7) 1.1011(4) -0.5488(7) 0.0284(15) Uani 1 1 d . . . H24 H -0.5061 1.0672 -0.4971 0.034 Uiso 1 1 calc R . . C25 C -0.7892(7) 1.0795(3) -0.8564(6) 0.0207(13) Uani 1 1 d . . . C26 C -0.8550(7) 1.1093(3) -0.7628(7) 0.0276(14) Uani 1 1 d . . . H26 H -0.8118 1.0931 -0.6604 0.033 Uiso 1 1 calc R . . C27 C -0.9828(8) 1.1623(3) -0.8180(8) 0.0345(16) Uani 1 1 d . . . H27 H -1.0273 1.1821 -0.7532 0.041 Uiso 1 1 calc R . . C28 C -1.0481(8) 1.1877(4) -0.9675(8) 0.0358(16) Uani 1 1 d . . . H28 H -1.1365 1.2241 -1.0051 0.043 Uiso 1 1 calc R . . C29 C -0.9811(7) 1.1584(3) -1.0591(7) 0.0296(15) Uani 1 1 d . . . H29 H -1.0235 1.1750 -1.1612 0.036 Uiso 1 1 calc R . . C30 C -0.8523(7) 1.1050(4) -1.0036(7) 0.0245(13) Uani 1 1 d . . . H30 H -0.8071 1.0856 -1.0682 0.029 Uiso 1 1 calc R . . Cl1 Cl -0.14907(18) 1.28920(9) -0.44977(17) 0.0321(4) Uani 1 1 d . . . Cl2 Cl 0.13197(19) 1.13821(9) -0.37361(18) 0.0338(4) 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 0.017(3) 0.023(3) 0.017(3) 0.001(2) 0.003(3) 0.000(2) N1 0.026(3) 0.022(2) 0.021(3) 0.0031(19) 0.013(2) -0.003(2) S1 0.0255(9) 0.0272(7) 0.0228(8) 0.0028(6) 0.0113(7) 0.0008(6) O1 0.063(4) 0.039(2) 0.028(2) -0.005(2) 0.025(3) -0.026(2) C3 0.041(4) 0.025(3) 0.022(3) 0.007(3) 0.017(3) 0.005(3) O2 0.032(3) 0.045(3) 0.029(3) 0.008(2) 0.019(2) 0.014(2) O3 0.018(2) 0.039(2) 0.023(2) 0.008(2) 0.004(2) 0.005(2) C4 0.032(4) 0.026(3) 0.025(3) 0.005(3) 0.015(3) 0.007(3) C5 0.022(4) 0.024(3) 0.028(3) 0.001(3) 0.008(3) -0.007(3) C6 0.021(4) 0.029(3) 0.032(4) -0.001(3) 0.013(3) 0.000(3) C7 0.035(4) 0.025(3) 0.032(4) 0.011(3) 0.024(3) 0.009(3) C8 0.038(4) 0.022(3) 0.032(4) 0.002(3) 0.025(4) 0.001(3) C9 0.015(3) 0.032(3) 0.013(3) -0.005(2) 0.002(3) -0.003(2) C10 0.029(4) 0.024(3) 0.026(3) 0.000(3) 0.014(3) 0.003(3) C11 0.032(4) 0.024(3) 0.033(4) 0.001(3) 0.020(3) 0.001(3) C12 0.038(4) 0.028(3) 0.028(4) -0.002(3) 0.018(3) 0.003(3) C13 0.034(4) 0.041(3) 0.019(4) -0.002(3) 0.010(3) 0.006(3) C14 0.035(4) 0.035(3) 0.031(4) 0.013(3) 0.020(3) 0.008(3) C15 0.025(4) 0.019(3) 0.031(3) -0.002(3) 0.012(3) 0.000(2) C16 0.018(3) 0.024(3) 0.019(3) 0.004(2) 0.008(3) 0.004(2) N2 0.041(3) 0.021(2) 0.027(3) 0.001(2) 0.025(3) -0.004(2) S2 0.0269(9) 0.0225(7) 0.0336(9) -0.0030(7) 0.0171(8) -0.0008(6) O4 0.045(3) 0.026(2) 0.033(2) -0.0087(18) 0.025(2) -0.012(2) C18 0.035(4) 0.022(3) 0.031(4) -0.001(3) 0.018(3) -0.003(3) O5 0.035(3) 0.025(2) 0.057(3) -0.008(2) 0.031(3) -0.0024(19) O6 0.033(3) 0.029(2) 0.046(3) 0.000(2) 0.017(3) -0.005(2) C19 0.014(3) 0.021(3) 0.034(4) 0.001(2) 0.010(3) 0.005(2) C20 0.022(4) 0.025(3) 0.032(4) 0.001(3) 0.016(3) 0.004(3) C21 0.023(4) 0.026(3) 0.032(4) 0.000(3) 0.015(3) 0.004(3) C22 0.020(4) 0.029(3) 0.033(4) -0.003(3) 0.010(3) -0.001(3) C23 0.025(4) 0.029(3) 0.028(4) -0.002(3) 0.009(3) 0.001(3) C24 0.035(4) 0.024(3) 0.036(4) 0.002(3) 0.024(4) 0.004(3) C25 0.017(3) 0.019(3) 0.019(3) 0.006(2) 0.001(3) 0.002(2) C26 0.028(4) 0.025(3) 0.030(4) -0.004(3) 0.012(3) -0.004(3) C27 0.029(4) 0.028(3) 0.052(5) -0.008(3) 0.022(4) 0.003(3) C28 0.031(4) 0.020(3) 0.056(5) 0.002(3) 0.018(4) 0.005(3) C29 0.016(4) 0.027(3) 0.032(4) 0.003(3) -0.003(3) -0.001(3) C30 0.023(4) 0.023(3) 0.022(3) -0.003(2) 0.004(3) -0.008(3) Cl1 0.0305(10) 0.0238(7) 0.0382(9) -0.0029(6) 0.0103(8) -0.0026(7) Cl2 0.0344(10) 0.0326(7) 0.0389(9) 0.0089(6) 0.0197(8) 0.0111(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.471(7) . ? C1 C10 1.522(7) . ? C1 C4 1.541(8) . ? C1 C3 1.563(7) . ? N1 S1 1.635(4) . ? N1 H31 0.8800 . ? S1 O3 1.409(4) . ? S1 O2 1.434(4) . ? S1 O1 1.585(4) . ? O1 C3 1.444(7) . ? C3 H32 0.9900 . ? C3 H33 0.9900 . ? C4 C9 1.378(8) . ? C4 C5 1.386(8) . ? C5 C6 1.383(8) . ? C5 H5 0.9500 . ? C6 C7 1.380(8) . ? C6 H6 0.9500 . ? C7 C8 1.369(8) . ? C7 Cl2 1.745(6) . ? C8 C9 1.405(8) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C15 1.378(7) . ? C10 C11 1.397(8) . ? C11 C12 1.370(7) . ? C11 H11 0.9500 . ? C12 C13 1.390(8) . ? C12 H12 0.9500 . ? C13 C14 1.384(9) . ? C13 H13 0.9500 . ? C14 C15 1.401(8) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 N2 1.490(7) . ? C16 C19 1.503(8) . ? C16 C25 1.549(8) . ? C16 C18 1.565(7) . ? N2 S2 1.640(5) . ? N2 H34 0.8800 . ? S2 O5 1.421(4) . ? S2 O6 1.428(5) . ? S2 O4 1.572(4) . ? O4 C18 1.460(7) . ? C18 H35 0.9900 . ? C18 H36 0.9900 . ? C19 C24 1.385(8) . ? C19 C20 1.411(7) . ? C20 C21 1.355(8) . ? C20 H20 0.9500 . ? C21 C22 1.377(8) . ? C21 H21 0.9500 . ? C22 C23 1.388(8) . ? C22 Cl1 1.741(6) . ? C23 C24 1.372(8) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.376(8) . ? C25 C26 1.389(7) . ? C26 C27 1.376(8) . ? C26 H26 0.9500 . ? C27 C28 1.395(9) . ? C27 H27 0.9500 . ? C28 C29 1.377(8) . ? C28 H28 0.9500 . ? C29 C30 1.388(8) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? 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 C10 110.4(4) . . ? N1 C1 C4 110.6(4) . . ? C10 C1 C4 108.4(5) . . ? N1 C1 C3 102.7(4) . . ? C10 C1 C3 111.2(4) . . ? C4 C1 C3 113.4(5) . . ? C1 N1 S1 108.6(3) . . ? C1 N1 H31 125.7 . . ? S1 N1 H31 125.7 . . ? O3 S1 O2 118.4(3) . . ? O3 S1 O1 110.8(3) . . ? O2 S1 O1 105.6(3) . . ? O3 S1 N1 111.7(2) . . ? O2 S1 N1 110.9(2) . . ? O1 S1 N1 97.1(2) . . ? C3 O1 S1 112.8(3) . . ? O1 C3 C1 106.3(4) . . ? O1 C3 H32 110.5 . . ? C1 C3 H32 110.5 . . ? O1 C3 H33 110.5 . . ? C1 C3 H33 110.5 . . ? H32 C3 H33 108.7 . . ? C9 C4 C5 118.7(6) . . ? C9 C4 C1 122.0(6) . . ? C5 C4 C1 119.1(5) . . ? C6 C5 C4 121.0(6) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 119.1(6) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C8 C7 C6 121.7(6) . . ? C8 C7 Cl2 119.0(4) . . ? C6 C7 Cl2 119.2(5) . . ? C7 C8 C9 118.2(5) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C4 C9 C8 121.3(6) . . ? C4 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C15 C10 C11 119.0(5) . . ? C15 C10 C1 121.6(5) . . ? C11 C10 C1 119.2(5) . . ? C12 C11 C10 121.0(5) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.9(6) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.1(5) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 119.5(5) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C10 C15 C14 120.5(5) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? N2 C16 C19 110.6(4) . . ? N2 C16 C25 110.1(5) . . ? C19 C16 C25 108.3(4) . . ? N2 C16 C18 102.5(4) . . ? C19 C16 C18 112.6(5) . . ? C25 C16 C18 112.7(4) . . ? C16 N2 S2 108.6(3) . . ? C16 N2 H34 125.7 . . ? S2 N2 H34 125.7 . . ? O5 S2 O6 118.3(3) . . ? O5 S2 O4 109.7(2) . . ? O6 S2 O4 106.5(2) . . ? O5 S2 N2 110.9(2) . . ? O6 S2 N2 111.4(3) . . ? O4 S2 N2 98.0(2) . . ? C18 O4 S2 112.7(3) . . ? O4 C18 C16 106.5(4) . . ? O4 C18 H35 110.4 . . ? C16 C18 H35 110.4 . . ? O4 C18 H36 110.4 . . ? C16 C18 H36 110.4 . . ? H35 C18 H36 108.6 . . ? C24 C19 C20 118.5(6) . . ? C24 C19 C16 120.8(5) . . ? C20 C19 C16 120.5(5) . . ? C21 C20 C19 121.1(6) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C22 119.7(5) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C21 C22 C23 120.3(6) . . ? C21 C22 Cl1 120.4(4) . . ? C23 C22 Cl1 119.3(5) . . ? C24 C23 C22 120.2(6) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C19 120.2(5) . . ? C23 C24 H24 119.9 . . ? C19 C24 H24 119.9 . . ? C30 C25 C26 119.0(6) . . ? C30 C25 C16 121.7(5) . . ? C26 C25 C16 118.8(5) . . ? C27 C26 C25 120.0(6) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 121.2(6) . . ? C26 C27 H27 119.4 . . ? C28 C27 H27 119.4 . . ? C29 C28 C27 118.3(6) . . ? C29 C28 H28 120.9 . . ? C27 C28 H28 120.9 . . ? C28 C29 C30 120.6(6) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C25 C30 C29 120.9(6) . . ? C25 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? 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 C10 C1 N1 S1 -154.8(4) . . . . ? C4 C1 N1 S1 85.1(4) . . . . ? C3 C1 N1 S1 -36.1(4) . . . . ? C1 N1 S1 O3 142.6(3) . . . . ? C1 N1 S1 O2 -82.8(4) . . . . ? C1 N1 S1 O1 26.9(4) . . . . ? O3 S1 O1 C3 -123.2(4) . . . . ? O2 S1 O1 C3 107.5(4) . . . . ? N1 S1 O1 C3 -6.7(5) . . . . ? S1 O1 C3 C1 -14.2(6) . . . . ? N1 C1 C3 O1 30.9(6) . . . . ? C10 C1 C3 O1 149.0(5) . . . . ? C4 C1 C3 O1 -88.5(6) . . . . ? N1 C1 C4 C9 16.9(7) . . . . ? C10 C1 C4 C9 -104.3(6) . . . . ? C3 C1 C4 C9 131.7(5) . . . . ? N1 C1 C4 C5 -168.4(5) . . . . ? C10 C1 C4 C5 70.4(6) . . . . ? C3 C1 C4 C5 -53.6(7) . . . . ? C9 C4 C5 C6 -1.3(8) . . . . ? C1 C4 C5 C6 -176.2(5) . . . . ? C4 C5 C6 C7 0.7(8) . . . . ? C5 C6 C7 C8 0.5(8) . . . . ? C5 C6 C7 Cl2 178.8(4) . . . . ? C6 C7 C8 C9 -1.0(8) . . . . ? Cl2 C7 C8 C9 -179.3(4) . . . . ? C5 C4 C9 C8 0.8(8) . . . . ? C1 C4 C9 C8 175.5(5) . . . . ? C7 C8 C9 C4 0.4(8) . . . . ? N1 C1 C10 C15 -39.5(7) . . . . ? C4 C1 C10 C15 81.8(7) . . . . ? C3 C1 C10 C15 -152.9(6) . . . . ? N1 C1 C10 C11 145.3(5) . . . . ? C4 C1 C10 C11 -93.4(6) . . . . ? C3 C1 C10 C11 31.9(8) . . . . ? C15 C10 C11 C12 0.7(9) . . . . ? C1 C10 C11 C12 176.1(5) . . . . ? C10 C11 C12 C13 -1.2(9) . . . . ? C11 C12 C13 C14 0.5(9) . . . . ? C12 C13 C14 C15 0.7(9) . . . . ? C11 C10 C15 C14 0.5(9) . . . . ? C1 C10 C15 C14 -174.8(6) . . . . ? C13 C14 C15 C10 -1.2(9) . . . . ? C19 C16 N2 S2 155.0(4) . . . . ? C25 C16 N2 S2 -85.3(4) . . . . ? C18 C16 N2 S2 34.8(5) . . . . ? C16 N2 S2 O5 -139.8(4) . . . . ? C16 N2 S2 O6 86.2(4) . . . . ? C16 N2 S2 O4 -25.1(4) . . . . ? O5 S2 O4 C18 120.5(4) . . . . ? O6 S2 O4 C18 -110.3(4) . . . . ? N2 S2 O4 C18 4.9(5) . . . . ? S2 O4 C18 C16 15.6(6) . . . . ? N2 C16 C18 O4 -30.9(6) . . . . ? C19 C16 C18 O4 -149.7(5) . . . . ? C25 C16 C18 O4 87.4(5) . . . . ? N2 C16 C19 C24 -145.7(5) . . . . ? C25 C16 C19 C24 93.5(6) . . . . ? C18 C16 C19 C24 -31.8(7) . . . . ? N2 C16 C19 C20 40.9(7) . . . . ? C25 C16 C19 C20 -79.9(6) . . . . ? C18 C16 C19 C20 154.9(5) . . . . ? C24 C19 C20 C21 1.7(8) . . . . ? C16 C19 C20 C21 175.2(5) . . . . ? C19 C20 C21 C22 -1.0(8) . . . . ? C20 C21 C22 C23 -0.2(8) . . . . ? C20 C21 C22 Cl1 -178.5(4) . . . . ? C21 C22 C23 C24 0.7(9) . . . . ? Cl1 C22 C23 C24 179.0(4) . . . . ? C22 C23 C24 C19 0.0(9) . . . . ? C20 C19 C24 C23 -1.2(8) . . . . ? C16 C19 C24 C23 -174.7(5) . . . . ? N2 C16 C25 C30 -20.7(7) . . . . ? C19 C16 C25 C30 100.3(6) . . . . ? C18 C16 C25 C30 -134.5(5) . . . . ? N2 C16 C25 C26 167.2(5) . . . . ? C19 C16 C25 C26 -71.7(6) . . . . ? C18 C16 C25 C26 53.5(6) . . . . ? C30 C25 C26 C27 1.0(8) . . . . ? C16 C25 C26 C27 173.3(5) . . . . ? C25 C26 C27 C28 -0.4(8) . . . . ? C26 C27 C28 C29 -0.2(9) . . . . ? C27 C28 C29 C30 0.2(9) . . . . ? C26 C25 C30 C29 -1.0(8) . . . . ? C16 C25 C30 C29 -173.0(5) . . . . ? C28 C29 C30 C25 0.4(8) . . . . ? 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 N1 H31 O6 0.88 2.60 3.099(6) 117.2 1_756 N2 H34 O2 0.88 2.46 3.048(6) 124.4 1_454 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 63.00 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.403 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.081 #------------------------------------------------------------ #-----------------------------------------------------------