# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Shujiang Tu' _publ_contact_author_email LAOTU@XZNU.EDU.CN _publ_section_title ; An efficient and chemoselective synthesis of benzo[e][1,4]thiazepin-2(1H,3H,5H)-ones via microwave-assisted multi-component reaction in water ; loop_ _publ_author_name 'Shujiang Tu' 'Xu-Dong Cao' 'Zheng-Guo Han' 'Wen-Juan Hao' 'Feng Shi' ; Shan-Shan Wu ; 'Shu Yan' 'Xiao-Hong Zhang' # Attachment '4a.cif' data_080304a _database_code_depnum_ccdc_archive 'CCDC 706679' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 N O S' _chemical_formula_weight 283.38 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 Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 14.4220(12) _cell_length_b 25.714(3) _cell_length_c 7.9543(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2949.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2278 _cell_measurement_theta_min 2.764 _cell_measurement_theta_max 25.395 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9288 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 13275 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2603 _reflns_number_gt 1516 _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^)+(0.0029P)^2^+5.8831P] 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 2603 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1096 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _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 N1 N 0.3560(2) 0.70806(12) 1.0905(4) 0.0443(9) Uani 1 1 d . . . H1 H 0.3411 0.7391 1.0605 0.053 Uiso 1 1 calc R . . O1 O 0.2051(2) 0.68471(11) 1.0847(5) 0.0670(10) Uani 1 1 d . . . S1 S 0.36281(7) 0.58078(4) 0.99417(14) 0.0447(3) Uani 1 1 d . . . C1 C 0.2870(3) 0.67322(16) 1.1091(6) 0.0477(11) Uani 1 1 d . . . C2 C 0.3162(3) 0.61952(14) 1.1642(5) 0.0484(11) Uani 1 1 d . . . H2A H 0.2630 0.6017 1.2118 0.058 Uiso 1 1 calc R . . H2B H 0.3627 0.6226 1.2518 0.058 Uiso 1 1 calc R . . C3 C 0.4419(3) 0.62762(14) 0.8946(5) 0.0346(9) Uani 1 1 d . . . H3 H 0.4034 0.6526 0.8333 0.042 Uiso 1 1 calc R . . C4 C 0.4966(2) 0.65827(13) 1.0244(5) 0.0333(9) Uani 1 1 d . . . C5 C 0.4519(3) 0.69728(14) 1.1167(5) 0.0386(10) Uani 1 1 d . . . C6 C 0.5006(3) 0.72691(15) 1.2299(5) 0.0486(11) Uani 1 1 d . . . H6 H 0.4705 0.7532 1.2891 0.058 Uiso 1 1 calc R . . C7 C 0.5940(3) 0.71794(17) 1.2566(6) 0.0539(12) Uani 1 1 d . . . H7 H 0.6260 0.7380 1.3346 0.065 Uiso 1 1 calc R . . C8 C 0.6407(3) 0.67935(17) 1.1686(5) 0.0462(11) Uani 1 1 d . . . C9 C 0.5900(3) 0.65048(15) 1.0539(5) 0.0381(10) Uani 1 1 d . . . H9 H 0.6204 0.6246 0.9938 0.046 Uiso 1 1 calc R . . C10 C 0.7421(3) 0.66800(19) 1.1970(6) 0.0760(16) Uani 1 1 d . . . H10A H 0.7786 0.6873 1.1177 0.114 Uiso 1 1 calc R . . H10B H 0.7533 0.6315 1.1822 0.114 Uiso 1 1 calc R . . H10C H 0.7590 0.6780 1.3092 0.114 Uiso 1 1 calc R . . C11 C 0.4980(3) 0.59830(14) 0.7652(5) 0.0351(9) Uani 1 1 d . . . C12 C 0.5003(3) 0.61601(15) 0.6015(5) 0.0432(10) Uani 1 1 d . . . H12 H 0.4673 0.6458 0.5730 0.052 Uiso 1 1 calc R . . C13 C 0.5509(3) 0.59010(16) 0.4782(5) 0.0512(11) Uani 1 1 d . . . H13 H 0.5510 0.6027 0.3686 0.061 Uiso 1 1 calc R . . C14 C 0.6011(3) 0.54568(16) 0.5174(6) 0.0485(11) Uani 1 1 d . . . C15 C 0.5975(3) 0.52758(16) 0.6800(6) 0.0511(12) Uani 1 1 d . . . H15 H 0.6299 0.4976 0.7083 0.061 Uiso 1 1 calc R . . C16 C 0.5469(3) 0.55294(15) 0.8016(5) 0.0464(11) Uani 1 1 d . . . H16 H 0.5453 0.5396 0.9102 0.056 Uiso 1 1 calc R . . C17 C 0.6570(3) 0.51768(19) 0.3853(6) 0.0770(16) Uani 1 1 d . . . H17A H 0.7219 0.5227 0.4067 0.115 Uiso 1 1 calc R . . H17B H 0.6418 0.5313 0.2763 0.115 Uiso 1 1 calc R . . H17C H 0.6429 0.4812 0.3887 0.115 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 N1 0.0321(18) 0.0368(18) 0.064(2) 0.0031(17) 0.0080(19) 0.0007(16) O1 0.0320(17) 0.0502(18) 0.119(3) 0.0012(19) 0.0061(19) 0.0024(15) S1 0.0422(6) 0.0391(5) 0.0529(6) 0.0015(5) 0.0060(6) -0.0041(5) C1 0.039(3) 0.047(3) 0.057(3) -0.002(2) 0.015(2) 0.000(2) C2 0.046(3) 0.042(2) 0.058(3) 0.010(2) 0.014(2) -0.001(2) C3 0.032(2) 0.036(2) 0.036(2) 0.0014(17) -0.0029(19) 0.0028(17) C4 0.032(2) 0.035(2) 0.033(2) 0.0010(18) 0.0009(18) -0.0017(17) C5 0.036(2) 0.037(2) 0.043(2) 0.002(2) 0.005(2) -0.0031(19) C6 0.053(3) 0.042(2) 0.052(3) -0.009(2) 0.008(2) -0.004(2) C7 0.059(3) 0.055(3) 0.048(3) -0.009(2) -0.009(2) -0.014(2) C8 0.039(2) 0.055(3) 0.045(2) 0.004(2) -0.005(2) -0.011(2) C9 0.035(2) 0.043(2) 0.037(2) 0.0012(18) 0.0030(19) 0.0015(19) C10 0.044(3) 0.100(4) 0.085(4) -0.011(3) -0.023(3) -0.004(3) C11 0.036(2) 0.036(2) 0.033(2) -0.0007(17) -0.0014(19) -0.0004(19) C12 0.045(3) 0.043(2) 0.042(2) 0.007(2) 0.003(2) 0.006(2) C13 0.055(3) 0.062(3) 0.036(2) 0.000(2) 0.008(2) 0.004(2) C14 0.043(3) 0.051(3) 0.052(3) -0.009(2) 0.007(2) 0.000(2) C15 0.052(3) 0.040(2) 0.062(3) -0.003(2) -0.001(2) 0.009(2) C16 0.054(3) 0.038(2) 0.047(3) 0.004(2) 0.001(2) 0.011(2) C17 0.069(4) 0.087(4) 0.075(4) -0.027(3) 0.021(3) 0.011(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 N1 C1 1.346(5) . ? N1 C5 1.427(5) . ? N1 H1 0.8600 . ? O1 C1 1.233(4) . ? S1 C2 1.810(4) . ? S1 C3 1.839(4) . ? C1 C2 1.508(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C11 1.510(5) . ? C3 C4 1.520(5) . ? C3 H3 0.9800 . ? C4 C9 1.382(5) . ? C4 C5 1.401(5) . ? C5 C6 1.373(5) . ? C6 C7 1.384(6) . ? C6 H6 0.9300 . ? C7 C8 1.388(6) . ? C7 H7 0.9300 . ? C8 C9 1.385(5) . ? C8 C10 1.509(6) . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.380(5) . ? C11 C16 1.394(5) . ? C12 C13 1.392(5) . ? C12 H12 0.9300 . ? C13 C14 1.388(5) . ? C13 H13 0.9300 . ? C14 C15 1.375(6) . ? C14 C17 1.508(6) . ? C15 C16 1.376(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 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 C1 N1 C5 124.8(3) . . ? C1 N1 H1 117.6 . . ? C5 N1 H1 117.6 . . ? C2 S1 C3 101.08(17) . . ? O1 C1 N1 122.0(4) . . ? O1 C1 C2 122.1(4) . . ? N1 C1 C2 115.8(4) . . ? C1 C2 S1 113.0(3) . . ? C1 C2 H2A 109.0 . . ? S1 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? S1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C11 C3 C4 116.4(3) . . ? C11 C3 S1 107.4(2) . . ? C4 C3 S1 111.7(3) . . ? C11 C3 H3 107.0 . . ? C4 C3 H3 107.0 . . ? S1 C3 H3 107.0 . . ? C9 C4 C5 117.6(4) . . ? C9 C4 C3 123.1(3) . . ? C5 C4 C3 119.2(3) . . ? C6 C5 C4 120.4(4) . . ? C6 C5 N1 118.9(4) . . ? C4 C5 N1 120.6(4) . . ? C5 C6 C7 120.4(4) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C8 120.9(4) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 117.4(4) . . ? C9 C8 C10 120.4(4) . . ? C7 C8 C10 122.2(4) . . ? C4 C9 C8 123.3(4) . . ? C4 C9 H9 118.4 . . ? C8 C9 H9 118.4 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 117.4(4) . . ? C12 C11 C3 119.4(3) . . ? C16 C11 C3 123.2(3) . . ? C11 C12 C13 121.3(4) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 120.6(4) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 118.0(4) . . ? C15 C14 C17 120.9(4) . . ? C13 C14 C17 121.0(4) . . ? C14 C15 C16 121.4(4) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C15 C16 C11 121.3(4) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 C5 N1 C1 O1 -180.0(4) . . . . ? C5 N1 C1 C2 0.9(6) . . . . ? O1 C1 C2 S1 102.0(5) . . . . ? N1 C1 C2 S1 -78.8(4) . . . . ? C3 S1 C2 C1 46.1(3) . . . . ? C2 S1 C3 C11 171.3(3) . . . . ? C2 S1 C3 C4 42.6(3) . . . . ? C11 C3 C4 C9 -16.2(5) . . . . ? S1 C3 C4 C9 107.6(4) . . . . ? C11 C3 C4 C5 162.2(3) . . . . ? S1 C3 C4 C5 -74.0(4) . . . . ? C9 C4 C5 C6 1.0(6) . . . . ? C3 C4 C5 C6 -177.4(3) . . . . ? C9 C4 C5 N1 178.9(3) . . . . ? C3 C4 C5 N1 0.4(5) . . . . ? C1 N1 C5 C6 -123.6(4) . . . . ? C1 N1 C5 C4 58.5(6) . . . . ? C4 C5 C6 C7 -1.2(6) . . . . ? N1 C5 C6 C7 -179.1(4) . . . . ? C5 C6 C7 C8 0.7(7) . . . . ? C6 C7 C8 C9 0.0(6) . . . . ? C6 C7 C8 C10 -178.9(4) . . . . ? C5 C4 C9 C8 -0.3(6) . . . . ? C3 C4 C9 C8 178.1(4) . . . . ? C7 C8 C9 C4 -0.2(6) . . . . ? C10 C8 C9 C4 178.8(4) . . . . ? C4 C3 C11 C12 -107.9(4) . . . . ? S1 C3 C11 C12 126.2(3) . . . . ? C4 C3 C11 C16 73.5(5) . . . . ? S1 C3 C11 C16 -52.4(4) . . . . ? C16 C11 C12 C13 -1.2(6) . . . . ? C3 C11 C12 C13 -179.9(4) . . . . ? C11 C12 C13 C14 -0.4(6) . . . . ? C12 C13 C14 C15 1.4(6) . . . . ? C12 C13 C14 C17 -179.3(4) . . . . ? C13 C14 C15 C16 -1.0(7) . . . . ? C17 C14 C15 C16 179.8(4) . . . . ? C14 C15 C16 C11 -0.6(7) . . . . ? C12 C11 C16 C15 1.7(6) . . . . ? C3 C11 C16 C15 -179.7(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.266 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.062