# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_c59_119_a _database_code_depnum_ccdc_archive 'CCDC 859365' #TrackingRef 'C59_119_A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 Cl N O3 S' _chemical_formula_weight 327.81 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.8154(5) _cell_length_b 9.7255(4) _cell_length_c 14.9356(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.8080(10) _cell_angle_gamma 90.00 _cell_volume 1570.22(12) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.385 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19884 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3429 _reflns_number_gt 2873 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0461P)^2^+0.6064P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0020(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3429 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.93424(13) 0.91049(15) 0.10589(9) 0.0312(3) Uani 1 1 d . . . C2 C 0.98643(14) 0.80858(16) 0.05408(10) 0.0350(3) Uani 1 1 d . . . C3 C 0.93035(15) 0.77446(18) -0.02714(11) 0.0411(4) Uani 1 1 d . . . H3 H 0.9642 0.7075 -0.0634 0.049 Uiso 1 1 calc R . . C4 C 0.82235(15) 0.84220(19) -0.05356(10) 0.0410(4) Uani 1 1 d . . . C5 C 0.76811(15) 0.94138(18) -0.00286(11) 0.0402(4) Uani 1 1 d . . . H5 H 0.6955 0.9840 -0.0231 0.048 Uiso 1 1 calc R . . C6 C 0.82354(13) 0.97785(16) 0.07991(10) 0.0336(3) Uani 1 1 d . . . C7 C 0.79660(15) 1.07269(16) 0.15143(11) 0.0373(3) Uani 1 1 d . . . C8 C 0.89167(15) 1.05849(16) 0.21639(10) 0.0365(3) Uani 1 1 d . . . C9 C 1.0554(2) 0.5831(2) 0.15597(15) 0.0626(5) Uani 1 1 d . . . H9A H 0.9983 0.5300 0.1195 0.094 Uiso 1 1 calc R . . H9B H 1.0128 0.6220 0.2054 0.094 Uiso 1 1 calc R . . H9C H 1.1209 0.5247 0.1783 0.094 Uiso 1 1 calc R . . C10 C 0.68775(17) 1.1623(2) 0.15467(14) 0.0502(4) Uani 1 1 d . . . C11 C 0.59195(19) 1.1569(3) 0.08044(17) 0.0716(7) Uani 1 1 d . . . H11A H 0.5251 1.2177 0.0938 0.107 Uiso 1 1 calc R . . H11B H 0.5611 1.0647 0.0744 0.107 Uiso 1 1 calc R . . H11C H 0.6281 1.1848 0.0254 0.107 Uiso 1 1 calc R . . C12 C 0.91833(17) 1.12379(18) 0.30776(12) 0.0466(4) Uani 1 1 d . . . C13 C 0.9379(3) 1.2796(2) 0.29660(17) 0.0720(7) Uani 1 1 d . . . H13A H 1.0056 1.2954 0.2578 0.108 Uiso 1 1 calc R . . H13B H 0.9564 1.3202 0.3541 0.108 Uiso 1 1 calc R . . H13C H 0.8641 1.3203 0.2710 0.108 Uiso 1 1 calc R . . C14 C 0.8115(2) 1.0948(3) 0.37025(13) 0.0648(6) Uani 1 1 d . . . H14A H 0.7366 1.1339 0.3453 0.097 Uiso 1 1 calc R . . H14B H 0.8297 1.1349 0.4279 0.097 Uiso 1 1 calc R . . H14C H 0.8013 0.9972 0.3767 0.097 Uiso 1 1 calc R . . C15 C 1.0365(2) 1.0635(2) 0.35176(13) 0.0621(5) Uani 1 1 d . . . H15A H 1.0272 0.9659 0.3584 0.093 Uiso 1 1 calc R . . H15B H 1.0507 1.1046 0.4096 0.093 Uiso 1 1 calc R . . H15C H 1.1056 1.0822 0.3148 0.093 Uiso 1 1 calc R . . Cl1 Cl 0.75403(5) 0.79588(6) -0.15641(3) 0.06394(18) Uani 1 1 d . . . N1 N 0.97275(11) 0.96301(13) 0.18696(8) 0.0339(3) Uani 1 1 d . . . H1 H 1.0395 0.9388 0.2156 0.041 Uiso 1 1 calc R . . O1 O 1.18971(12) 0.80178(14) 0.15040(10) 0.0574(4) Uani 1 1 d . . . O2 O 1.17356(15) 0.65500(19) 0.01607(10) 0.0779(5) Uani 1 1 d . . . O3 O 0.67108(16) 1.24081(19) 0.21666(11) 0.0828(5) Uani 1 1 d . . . S1 S 1.11728(4) 0.71504(5) 0.09173(3) 0.04409(14) 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 0.0331(7) 0.0304(7) 0.0303(7) 0.0014(6) 0.0034(6) 0.0000(6) C2 0.0355(8) 0.0353(8) 0.0343(8) 0.0008(6) 0.0026(6) 0.0051(6) C3 0.0469(9) 0.0417(9) 0.0351(8) -0.0068(7) 0.0043(7) 0.0019(7) C4 0.0415(8) 0.0508(10) 0.0306(7) 0.0000(7) -0.0018(6) -0.0055(7) C5 0.0329(8) 0.0483(10) 0.0392(8) 0.0052(7) -0.0003(6) 0.0016(7) C6 0.0328(7) 0.0323(7) 0.0360(7) 0.0033(6) 0.0055(6) 0.0007(6) C7 0.0393(8) 0.0330(8) 0.0401(8) 0.0005(6) 0.0090(6) 0.0038(6) C8 0.0415(8) 0.0303(8) 0.0383(8) -0.0019(6) 0.0098(6) -0.0021(6) C9 0.0708(13) 0.0452(11) 0.0718(13) 0.0124(10) -0.0007(11) 0.0080(10) C10 0.0469(10) 0.0431(10) 0.0616(11) 0.0037(9) 0.0160(8) 0.0109(8) C11 0.0461(11) 0.0752(15) 0.0933(17) -0.0065(13) -0.0013(11) 0.0271(11) C12 0.0563(10) 0.0411(9) 0.0428(9) -0.0118(7) 0.0091(8) -0.0043(8) C13 0.0941(17) 0.0437(11) 0.0790(15) -0.0213(11) 0.0150(13) -0.0113(11) C14 0.0725(14) 0.0763(15) 0.0468(11) -0.0129(10) 0.0194(10) -0.0050(11) C15 0.0671(13) 0.0729(14) 0.0455(10) -0.0184(10) -0.0078(9) -0.0031(11) Cl1 0.0587(3) 0.0911(4) 0.0412(3) -0.0132(2) -0.0117(2) -0.0038(3) N1 0.0355(6) 0.0343(7) 0.0320(6) -0.0023(5) 0.0009(5) 0.0018(5) O1 0.0453(7) 0.0584(8) 0.0676(9) 0.0066(7) -0.0128(6) 0.0051(6) O2 0.0768(10) 0.0995(12) 0.0583(9) -0.0026(8) 0.0175(8) 0.0496(9) O3 0.0866(12) 0.0818(11) 0.0804(12) -0.0233(9) 0.0099(9) 0.0426(9) S1 0.0430(2) 0.0469(3) 0.0425(2) 0.00184(18) 0.00432(17) 0.01604(18) _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 1.3669(18) . ? C1 C2 1.388(2) . ? C1 C6 1.408(2) . ? C2 C3 1.380(2) . ? C2 S1 1.7597(15) . ? C3 C4 1.387(2) . ? C4 C5 1.370(2) . ? C4 Cl1 1.7427(16) . ? C5 C6 1.402(2) . ? C6 C7 1.448(2) . ? C7 C8 1.398(2) . ? C7 C10 1.467(2) . ? C8 N1 1.360(2) . ? C8 C12 1.524(2) . ? C9 S1 1.748(2) . ? C10 O3 1.218(2) . ? C10 C11 1.494(3) . ? C12 C14 1.534(3) . ? C12 C15 1.535(3) . ? C12 C13 1.540(3) . ? O1 S1 1.4316(14) . ? O2 S1 1.4254(14) . ? 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 129.99(14) . . ? N1 C1 C6 107.63(13) . . ? C2 C1 C6 122.38(14) . . ? C3 C2 C1 119.13(14) . . ? C3 C2 S1 118.91(12) . . ? C1 C2 S1 121.87(12) . . ? C2 C3 C4 118.60(15) . . ? C5 C4 C3 123.27(15) . . ? C5 C4 Cl1 119.49(13) . . ? C3 C4 Cl1 117.24(13) . . ? C4 C5 C6 119.13(15) . . ? C5 C6 C1 117.47(14) . . ? C5 C6 C7 136.14(15) . . ? C1 C6 C7 106.39(13) . . ? C8 C7 C6 106.76(13) . . ? C8 C7 C10 127.53(15) . . ? C6 C7 C10 125.69(15) . . ? N1 C8 C7 108.11(13) . . ? N1 C8 C12 117.92(14) . . ? C7 C8 C12 133.97(15) . . ? O3 C10 C7 122.40(19) . . ? O3 C10 C11 118.06(18) . . ? C7 C10 C11 119.53(17) . . ? C8 C12 C14 110.06(15) . . ? C8 C12 C15 110.82(14) . . ? C14 C12 C15 107.59(17) . . ? C8 C12 C13 109.63(16) . . ? C14 C12 C13 110.85(17) . . ? C15 C12 C13 107.85(18) . . ? C8 N1 C1 111.10(13) . . ? O2 S1 O1 119.17(10) . . ? O2 S1 C9 108.35(11) . . ? O1 S1 C9 107.96(10) . . ? O2 S1 C2 108.52(8) . . ? O1 S1 C2 108.06(8) . . ? C9 S1 C2 103.70(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.266 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.040