Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Jeon, Moon-Kook' 'Kim, Kyongtae' 'Park, Yung Ja' _publ_contact_author_name 'Prof Kyongtae Kim' _publ_contact_author_address ; Prof Kyongtae Kim School of Chemistry and Molecular Engineering Seoul National University Seoul 151-742 KOREA ; _publ_contact_author_email 'KKIM@PLAZA.SNU.AC.KR' _publ_section_title ; Novel synthesis of 1-aryl-3-chloro-3-phenylazetidin-2-one-4-spiro-5'-4'chloro-5'H-1',2'3'-dithi azoles and bis (azetidin-2-oxo-4-yl) trisulfides ; data_a _database_code_CSD 165871 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H9 Cl3 N2 O S2' _chemical_formula_weight 415.72 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' 'O' 'O' 0.0106 0.0060 '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' '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 P2/k _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 16.946(2) _cell_length_b 7.4460(5) _cell_length_c 15.026(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.080(10) _cell_angle_gamma 90.00 _cell_volume 1744.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PRISM _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.622mm _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.282 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.770 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3189 _diffrn_reflns_av_R_equivalents 0.0088 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3057 _reflns_number_gt 2499 _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 w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+1.6903P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3057 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.11334(19) 0.6835(4) 0.9924(2) 0.0398(7) Uani 1 d . . . C2 C 0.0293(2) 0.7055(5) 0.9278(2) 0.0482(8) Uani 1 d . . . H2 H 0.0148 0.6903 0.8618 0.058 Uiso 1 calc R . . C3 C -0.0326(2) 0.7499(5) 0.9618(3) 0.0548(9) Uani 1 d . . . H3 H -0.0892 0.7653 0.9188 0.066 Uiso 1 calc R . . C4 C -0.0109(2) 0.7713(5) 1.0592(3) 0.0500(8) Uani 1 d . . . C5 C 0.0724(2) 0.7495(5) 1.1240(3) 0.0559(9) Uani 1 d . . . H5 H 0.0867 0.7642 1.1899 0.067 Uiso 1 calc R . . C6 C 0.1346(2) 0.7057(5) 1.0901(2) 0.0512(8) Uani 1 d . . . H6 H 0.1912 0.6910 1.1333 0.061 Uiso 1 calc R . . C7 C 0.1756(2) 0.6220(5) 0.8654(2) 0.0490(8) Uani 1 d . . . C8 C 0.27026(19) 0.5727(4) 0.9027(2) 0.0395(7) Uani 1 d . . . C9 C 0.26636(18) 0.5904(4) 1.00793(19) 0.0349(6) Uani 1 d . . . C10 C 0.32264(18) 0.7354(4) 1.0734(2) 0.0372(6) Uani 1 d . . . C11 C 0.3315(2) 0.6933(4) 0.8817(2) 0.0418(7) Uani 1 d . . . C12 C 0.3016(3) 0.8196(5) 0.8082(2) 0.0600(9) Uani 1 d . . . H12 H 0.2434 0.8281 0.7696 0.072 Uiso 1 calc R . . C13 C 0.3608(4) 0.9338(6) 0.7933(3) 0.0820(14) Uani 1 d . . . H13 H 0.3414 1.0200 0.7447 0.098 Uiso 1 calc R . . C14 C 0.4463(4) 0.9212(7) 0.8489(3) 0.0819(14) Uani 1 d . . . H14 H 0.4848 0.9978 0.8378 0.098 Uiso 1 calc R . . C15 C 0.4754(3) 0.7955(6) 0.9211(3) 0.0681(11) Uani 1 d . . . H15 H 0.5337 0.7870 0.9594 0.082 Uiso 1 calc R . . C16 C 0.4181(2) 0.6815(5) 0.9368(2) 0.0494(8) Uani 1 d . . . H16 H 0.4382 0.5954 0.9853 0.059 Uiso 1 calc R . . O O 0.12017(16) 0.6428(5) 0.78660(16) 0.0766(9) Uani 1 d . . . N1 N 0.17646(15) 0.6366(3) 0.95675(16) 0.0397(6) Uani 1 d . . . N2 N 0.38145(17) 0.7053(4) 1.15580(18) 0.0498(7) Uani 1 d . . . S1 S 0.28508(6) 0.38958(11) 1.08206(6) 0.0561(3) Uani 1 d . . . S2 S 0.39084(6) 0.49369(15) 1.19315(7) 0.0684(3) Uani 1 d . . . Cl1 Cl -0.09072(6) 0.82209(16) 1.10098(8) 0.0761(3) Uani 1 d . . . Cl2 Cl 0.28348(6) 0.34561(11) 0.87248(7) 0.0579(3) Uani 1 d . . . Cl3 Cl 0.30209(6) 0.95233(10) 1.03288(6) 0.0579(3) Uani 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 0.0413(15) 0.0373(15) 0.0376(15) 0.0019(12) 0.0119(12) -0.0008(12) C2 0.0423(16) 0.0541(19) 0.0402(16) 0.0030(15) 0.0075(13) -0.0019(15) C3 0.0405(17) 0.062(2) 0.056(2) 0.0100(17) 0.0129(15) 0.0025(16) C4 0.0476(18) 0.0464(18) 0.061(2) 0.0050(16) 0.0272(16) 0.0008(15) C5 0.058(2) 0.067(2) 0.0440(18) -0.0044(17) 0.0215(16) -0.0002(18) C6 0.0416(16) 0.070(2) 0.0389(16) 0.0003(16) 0.0120(13) 0.0037(16) C7 0.0538(18) 0.056(2) 0.0321(16) -0.0047(14) 0.0112(14) 0.0009(16) C8 0.0486(17) 0.0362(15) 0.0299(14) -0.0049(12) 0.0112(12) 0.0028(13) C9 0.0402(15) 0.0314(14) 0.0290(13) 0.0025(11) 0.0091(11) 0.0039(12) C10 0.0411(15) 0.0360(15) 0.0339(14) -0.0038(12) 0.0142(12) 0.0022(12) C11 0.0617(19) 0.0337(15) 0.0344(15) -0.0050(12) 0.0236(14) -0.0003(14) C12 0.086(3) 0.056(2) 0.0359(17) 0.0045(15) 0.0222(17) 0.0023(19) C13 0.145(5) 0.059(2) 0.056(2) 0.011(2) 0.055(3) -0.012(3) C14 0.117(4) 0.077(3) 0.075(3) -0.015(2) 0.063(3) -0.037(3) C15 0.074(3) 0.072(3) 0.072(3) -0.020(2) 0.042(2) -0.019(2) C16 0.0557(19) 0.0474(18) 0.0484(18) -0.0021(15) 0.0240(15) -0.0006(15) O 0.0560(15) 0.131(3) 0.0297(12) -0.0024(14) 0.0028(11) 0.0095(16) N1 0.0379(13) 0.0463(14) 0.0290(12) -0.0009(11) 0.0067(10) 0.0016(11) N2 0.0535(15) 0.0557(17) 0.0349(14) -0.0045(12) 0.0116(12) -0.0039(13) S1 0.0747(6) 0.0341(4) 0.0498(5) 0.0096(3) 0.0141(4) 0.0025(4) S2 0.0647(6) 0.0751(7) 0.0459(5) 0.0220(5) 0.0006(4) 0.0076(5) Cl1 0.0629(6) 0.0901(8) 0.0899(7) 0.0045(6) 0.0456(5) 0.0077(5) Cl2 0.0789(6) 0.0409(4) 0.0614(5) -0.0180(4) 0.0356(5) -0.0088(4) Cl3 0.0836(6) 0.0295(4) 0.0588(5) -0.0034(3) 0.0258(4) 0.0021(4) _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 C6 1.377(4) . ? C1 C2 1.383(4) . ? C1 N1 1.415(4) . ? C2 C3 1.376(5) . ? C3 C4 1.371(5) . ? C4 C5 1.375(5) . ? C4 Cl1 1.742(3) . ? C5 C6 1.377(5) . ? C7 O 1.198(4) . ? C7 N1 1.371(4) . ? C7 C8 1.522(4) . ? C8 C11 1.497(4) . ? C8 C9 1.613(4) . ? C8 Cl2 1.788(3) . ? C9 N1 1.453(4) . ? C9 C10 1.519(4) . ? C9 S1 1.817(3) . ? C10 N2 1.268(4) . ? C10 Cl3 1.713(3) . ? C11 C16 1.376(5) . ? C11 C12 1.386(5) . ? C12 C13 1.398(6) . ? C13 C14 1.363(7) . ? C14 C15 1.370(7) . ? C15 C16 1.378(5) . ? N2 S2 1.659(3) . ? S1 S2 2.0624(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 C6 C1 C2 120.1(3) . . ? C6 C1 N1 120.8(3) . . ? C2 C1 N1 119.1(3) . . ? C3 C2 C1 119.6(3) . . ? C4 C3 C2 119.9(3) . . ? C3 C4 C5 120.9(3) . . ? C3 C4 Cl1 119.2(3) . . ? C5 C4 Cl1 119.8(3) . . ? C4 C5 C6 119.2(3) . . ? C5 C6 C1 120.3(3) . . ? O C7 N1 132.5(3) . . ? O C7 C8 134.4(3) . . ? N1 C7 C8 93.1(2) . . ? C11 C8 C7 119.7(3) . . ? C11 C8 C9 117.1(2) . . ? C7 C8 C9 84.2(2) . . ? C11 C8 Cl2 110.3(2) . . ? C7 C8 Cl2 110.7(2) . . ? C9 C8 Cl2 112.6(2) . . ? N1 C9 C10 115.9(2) . . ? N1 C9 C8 86.4(2) . . ? C10 C9 C8 115.9(2) . . ? N1 C9 S1 114.5(2) . . ? C10 C9 S1 105.87(19) . . ? C8 C9 S1 117.98(19) . . ? N2 C10 C9 124.1(3) . . ? N2 C10 Cl3 119.1(2) . . ? C9 C10 Cl3 116.8(2) . . ? C16 C11 C12 119.6(3) . . ? C16 C11 C8 119.9(3) . . ? C12 C11 C8 120.5(3) . . ? C11 C12 C13 118.6(4) . . ? C14 C13 C12 121.1(4) . . ? C13 C14 C15 119.9(4) . . ? C14 C15 C16 119.8(4) . . ? C11 C16 C15 121.0(4) . . ? C7 N1 C1 133.3(2) . . ? C7 N1 C9 96.2(2) . . ? C1 N1 C9 130.5(2) . . ? C10 N2 S2 115.6(2) . . ? C9 S1 S2 94.26(10) . . ? N2 S2 S1 98.37(10) . . ? 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 C6 C1 C2 C3 0.2(5) . . . . ? N1 C1 C2 C3 179.6(3) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? C2 C3 C4 Cl1 -178.4(3) . . . . ? C3 C4 C5 C6 0.1(6) . . . . ? Cl1 C4 C5 C6 178.6(3) . . . . ? C4 C5 C6 C1 -0.2(6) . . . . ? C2 C1 C6 C5 0.1(5) . . . . ? N1 C1 C6 C5 -179.3(3) . . . . ? O C7 C8 C11 61.9(6) . . . . ? N1 C7 C8 C11 -117.5(3) . . . . ? O C7 C8 C9 179.9(5) . . . . ? N1 C7 C8 C9 0.5(2) . . . . ? O C7 C8 Cl2 -68.1(5) . . . . ? N1 C7 C8 Cl2 112.5(2) . . . . ? C11 C8 C9 N1 120.0(3) . . . . ? C7 C8 C9 N1 -0.5(2) . . . . ? Cl2 C8 C9 N1 -110.5(2) . . . . ? C11 C8 C9 C10 2.9(4) . . . . ? C7 C8 C9 C10 -117.6(3) . . . . ? Cl2 C8 C9 C10 132.4(2) . . . . ? C11 C8 C9 S1 -124.1(2) . . . . ? C7 C8 C9 S1 115.4(2) . . . . ? Cl2 C8 C9 S1 5.4(3) . . . . ? N1 C9 C10 N2 140.3(3) . . . . ? C8 C9 C10 N2 -120.6(3) . . . . ? S1 C9 C10 N2 12.3(4) . . . . ? N1 C9 C10 Cl3 -38.0(3) . . . . ? C8 C9 C10 Cl3 61.2(3) . . . . ? S1 C9 C10 Cl3 -166.01(15) . . . . ? C7 C8 C11 C16 160.8(3) . . . . ? C9 C8 C11 C16 61.5(4) . . . . ? Cl2 C8 C11 C16 -69.0(3) . . . . ? C7 C8 C11 C12 -17.9(4) . . . . ? C9 C8 C11 C12 -117.2(3) . . . . ? Cl2 C8 C11 C12 112.3(3) . . . . ? C16 C11 C12 C13 -1.0(5) . . . . ? C8 C11 C12 C13 177.7(3) . . . . ? C11 C12 C13 C14 0.7(6) . . . . ? C12 C13 C14 C15 -0.3(7) . . . . ? C13 C14 C15 C16 0.4(6) . . . . ? C12 C11 C16 C15 1.1(5) . . . . ? C8 C11 C16 C15 -177.6(3) . . . . ? C14 C15 C16 C11 -0.8(5) . . . . ? O C7 N1 C1 -1.0(7) . . . . ? C8 C7 N1 C1 178.4(3) . . . . ? O C7 N1 C9 -180.0(4) . . . . ? C8 C7 N1 C9 -0.6(3) . . . . ? C6 C1 N1 C7 -173.1(4) . . . . ? C2 C1 N1 C7 7.4(5) . . . . ? C6 C1 N1 C9 5.5(5) . . . . ? C2 C1 N1 C9 -173.9(3) . . . . ? C10 C9 N1 C7 117.6(3) . . . . ? C8 C9 N1 C7 0.5(2) . . . . ? S1 C9 N1 C7 -118.7(2) . . . . ? C10 C9 N1 C1 -61.4(4) . . . . ? C8 C9 N1 C1 -178.5(3) . . . . ? S1 C9 N1 C1 62.3(4) . . . . ? C9 C10 N2 S2 -3.6(4) . . . . ? Cl3 C10 N2 S2 174.68(16) . . . . ? N1 C9 S1 S2 -141.11(19) . . . . ? C10 C9 S1 S2 -12.24(19) . . . . ? C8 C9 S1 S2 119.4(2) . . . . ? C10 N2 S2 S1 -5.8(3) . . . . ? C9 S1 S2 N2 10.40(15) . . . . ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.421 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.067