# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Adam Daich' _publ_contact_author_address ; URCOM, EA 3221 University of Le Havre 25 Rue Philippe Lebon, BP 540 Le Havre Normandy 76058 FRANCE ; _publ_contact_author_email ADAM.DAICH@UNIV-LEHAVRE.FR _publ_section_title ; Acid-catalysed formation of tricyclic N,S-acetals in imidazolinone series based on the use of the unprecedented heterocyclisation/transposition/ isomerisation of N-acyliminium ion cascade ; loop_ _publ_author_name 'Adam Daich' 'Bernard Decroix' 'Anthony Pesquet' 'L.Van Hijfte' data_cap _database_code_depnum_ccdc_archive 'CCDC 266273' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 N2 O S' _chemical_formula_weight 234.31 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 monoclinic _symmetry_space_group_name_H-M P21/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 7.569(4) _cell_length_b 18.652(2) _cell_length_c 8.388(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.69(3) _cell_angle_gamma 90.00 _cell_volume 1150.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 2687 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 26.97 _reflns_number_total 2505 _reflns_number_gt 1868 _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^)+(0.0571P)^2^+0.0458P] 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 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2505 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 S1 S 0.75037(7) 0.01727(2) 0.05984(5) 0.04643(16) Uani 1 1 d . . . O1 O 0.56632(16) 0.20718(6) 0.27030(14) 0.0443(3) Uani 1 1 d . . . N1 N 0.80522(18) 0.12835(7) 0.27200(15) 0.0350(3) Uani 1 1 d . . . N2 N 0.7019(2) 0.19371(7) 0.05061(17) 0.0412(3) Uani 1 1 d . . . H21 H 0.646(3) 0.2258(10) -0.012(2) 0.050 Uiso 1 1 d . . . C1 C 0.7287(2) -0.02424(8) 0.2449(2) 0.0393(4) Uani 1 1 d . . . C2 C 0.6820(2) -0.09742(9) 0.2341(3) 0.0486(4) Uani 1 1 d . . . H2 H 0.6683 -0.1213 0.1346 0.058 Uiso 1 1 calc R . . C3 C 0.6562(2) -0.13428(10) 0.3700(3) 0.0566(5) Uani 1 1 d . . . H3 H 0.6238 -0.1825 0.3608 0.068 Uiso 1 1 calc R . . C4 C 0.6785(3) -0.09984(10) 0.5192(3) 0.0541(5) Uani 1 1 d . . . H4 H 0.6633 -0.1248 0.6110 0.065 Uiso 1 1 calc R . . C5 C 0.7236(2) -0.02761(9) 0.5308(2) 0.0468(4) Uani 1 1 d . . . H5 H 0.7369 -0.0043 0.6310 0.056 Uiso 1 1 calc R . . C6 C 0.7497(2) 0.01107(8) 0.3949(2) 0.0375(4) Uani 1 1 d . . . C7 C 0.7977(2) 0.08994(8) 0.42089(19) 0.0386(4) Uani 1 1 d . . . H7A H 0.7083 0.1129 0.4699 0.046 Uiso 1 1 calc R . . H7B H 0.9150 0.0939 0.4981 0.046 Uiso 1 1 calc R . . C8 C 0.6777(2) 0.17957(8) 0.20294(18) 0.0351(4) Uani 1 1 d . . . C9 C 0.8653(2) 0.15833(8) 0.02023(19) 0.0382(4) Uani 1 1 d . . . C10 C 0.8830(2) 0.09670(8) 0.14680(18) 0.0350(3) Uani 1 1 d . . . H10 H 1.0109 0.0842 0.1913 0.042 Uiso 1 1 calc R . . C11 C 0.8366(3) 0.13468(10) -0.1577(2) 0.0468(4) Uani 1 1 d . . . H11A H 0.7320 0.1040 -0.1860 0.056 Uiso 1 1 calc R . . H11B H 0.9419 0.1091 -0.1716 0.056 Uiso 1 1 calc R . . H11C H 0.8177 0.1761 -0.2278 0.056 Uiso 1 1 calc R . . C12 C 1.0312(3) 0.20757(10) 0.0685(2) 0.0542(5) Uani 1 1 d . . . H12A H 1.0475 0.2219 0.1810 0.065 Uiso 1 1 calc R . . H12B H 1.0126 0.2493 -0.0004 0.065 Uiso 1 1 calc R . . H12C H 1.1374 0.1824 0.0552 0.065 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 0.0622(3) 0.0362(2) 0.0408(2) -0.00689(17) 0.0121(2) -0.00617(19) O1 0.0528(7) 0.0353(6) 0.0485(7) 0.0000(5) 0.0198(6) 0.0074(5) N1 0.0446(8) 0.0290(6) 0.0315(6) 0.0005(5) 0.0094(5) 0.0020(5) N2 0.0516(9) 0.0367(7) 0.0367(7) 0.0067(6) 0.0131(6) 0.0113(6) C1 0.0331(8) 0.0328(9) 0.0504(10) 0.0030(7) 0.0066(7) 0.0013(6) C2 0.0435(10) 0.0337(9) 0.0665(12) -0.0030(8) 0.0089(9) -0.0026(7) C3 0.0429(10) 0.0349(9) 0.0877(15) 0.0126(10) 0.0070(10) -0.0037(7) C4 0.0445(10) 0.0477(10) 0.0680(13) 0.0240(9) 0.0089(9) -0.0018(8) C5 0.0439(10) 0.0475(10) 0.0474(10) 0.0123(8) 0.0075(8) 0.0034(7) C6 0.0329(8) 0.0344(8) 0.0436(8) 0.0066(7) 0.0055(7) 0.0034(6) C7 0.0485(10) 0.0351(8) 0.0319(8) 0.0018(6) 0.0086(7) 0.0023(7) C8 0.0419(9) 0.0264(7) 0.0366(8) -0.0018(6) 0.0082(7) -0.0014(6) C9 0.0438(9) 0.0350(8) 0.0366(8) 0.0009(6) 0.0114(7) 0.0017(7) C10 0.0371(8) 0.0327(8) 0.0343(8) -0.0010(6) 0.0067(6) 0.0023(6) C11 0.0582(11) 0.0466(10) 0.0381(9) 0.0013(7) 0.0164(8) 0.0061(8) C12 0.0605(12) 0.0502(10) 0.0551(11) -0.0013(8) 0.0198(9) -0.0123(9) _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 C1 1.7770(17) . ? S1 C10 1.8407(16) . ? O1 C8 1.2334(19) . ? N1 C8 1.384(2) . ? N1 C10 1.4458(19) . ? N1 C7 1.4525(19) . ? N2 C8 1.359(2) . ? N2 C9 1.476(2) . ? N2 H21 0.84(2) . ? C1 C6 1.395(2) . ? C1 C2 1.407(2) . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C3 C4 1.381(3) . ? C3 H3 0.9300 . ? C4 C5 1.388(2) . ? C4 H4 0.9300 . ? C5 C6 1.402(2) . ? C5 H5 0.9300 . ? C6 C7 1.519(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C11 1.522(2) . ? C9 C12 1.531(2) . ? C9 C10 1.549(2) . ? C10 H10 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 S1 C10 99.14(7) . . ? C8 N1 C10 109.95(12) . . ? C8 N1 C7 122.35(13) . . ? C10 N1 C7 121.91(12) . . ? C8 N2 C9 112.34(14) . . ? C8 N2 H21 124.2(13) . . ? C9 N2 H21 122.1(13) . . ? C6 C1 C2 119.29(16) . . ? C6 C1 S1 124.58(12) . . ? C2 C1 S1 116.10(14) . . ? C3 C2 C1 120.72(18) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C4 C3 C2 120.30(17) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.37(18) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 121.47(18) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 118.83(15) . . ? C1 C6 C7 124.00(14) . . ? C5 C6 C7 117.17(15) . . ? N1 C7 C6 114.27(13) . . ? N1 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? N1 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? O1 C8 N2 127.47(15) . . ? O1 C8 N1 125.53(14) . . ? N2 C8 N1 106.99(13) . . ? N2 C9 C11 111.57(14) . . ? N2 C9 C12 110.76(14) . . ? C11 C9 C12 110.57(14) . . ? N2 C9 C10 98.82(12) . . ? C11 C9 C10 115.24(13) . . ? C12 C9 C10 109.36(13) . . ? N1 C10 C9 102.17(11) . . ? N1 C10 S1 109.82(11) . . ? C9 C10 S1 112.04(10) . . ? N1 C10 H10 110.8 . . ? C9 C10 H10 110.8 . . ? S1 C10 H10 110.8 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C10 S1 C1 C6 20.25(15) . . . . ? C10 S1 C1 C2 -161.60(13) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? S1 C1 C2 C3 -178.01(14) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C2 C1 C6 C5 0.0(2) . . . . ? S1 C1 C6 C5 178.14(12) . . . . ? C2 C1 C6 C7 -179.31(15) . . . . ? S1 C1 C6 C7 -1.2(2) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C4 C5 C6 C7 179.67(16) . . . . ? C8 N1 C7 C6 110.46(16) . . . . ? C10 N1 C7 C6 -40.0(2) . . . . ? C1 C6 C7 N1 5.1(2) . . . . ? C5 C6 C7 N1 -174.27(14) . . . . ? C9 N2 C8 O1 171.55(15) . . . . ? C9 N2 C8 N1 -7.46(17) . . . . ? C10 N1 C8 O1 166.87(15) . . . . ? C7 N1 C8 O1 13.3(2) . . . . ? C10 N1 C8 N2 -14.09(16) . . . . ? C7 N1 C8 N2 -167.68(13) . . . . ? C8 N2 C9 C11 145.23(15) . . . . ? C8 N2 C9 C12 -91.15(16) . . . . ? C8 N2 C9 C10 23.54(16) . . . . ? C8 N1 C10 C9 28.20(15) . . . . ? C7 N1 C10 C9 -178.07(13) . . . . ? C8 N1 C10 S1 -90.86(13) . . . . ? C7 N1 C10 S1 62.87(16) . . . . ? N2 C9 C10 N1 -29.35(14) . . . . ? C11 C9 C10 N1 -148.33(14) . . . . ? C12 C9 C10 N1 86.41(16) . . . . ? N2 C9 C10 S1 88.13(13) . . . . ? C11 C9 C10 S1 -30.85(17) . . . . ? C12 C9 C10 S1 -156.11(12) . . . . ? C1 S1 C10 N1 -45.74(12) . . . . ? C1 S1 C10 C9 -158.54(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.274 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.040 data_ad _database_code_depnum_ccdc_archive 'CCDC 266274' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 N2 O S' _chemical_formula_weight 248.34 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 Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 19.225(8) _cell_length_b 10.950(4) _cell_length_c 6.047(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1273(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourles _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 1511 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.92 _reflns_number_total 1511 _reflns_number_gt 1209 _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^)+(0.1095P)^2^+0.1136P] 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 0.014(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.12(18) _refine_ls_number_reflns 1511 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1540 _refine_ls_wR_factor_gt 0.1457 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.98053(4) 0.31621(8) 0.5581(2) 0.0554(3) Uani 1 1 d . . . O1 O 0.78294(15) 0.1623(2) 0.7284(9) 0.0747(11) Uani 1 1 d . . . N1 N 0.87268(14) 0.2881(3) 0.8476(7) 0.0478(8) Uani 1 1 d . . . N2 N 0.81079(14) 0.3446(2) 0.5513(9) 0.0558(9) Uani 1 1 d . . . C1 C 1.01706(16) 0.2182(3) 0.7637(9) 0.0510(10) Uani 1 1 d . . . C2 C 1.0872(2) 0.1837(3) 0.7291(12) 0.0658(14) Uani 1 1 d . . . H2 H 1.1109 0.2107 0.6043 0.079 Uiso 1 1 calc R . . C3 C 1.1201(2) 0.1096(4) 0.8818(14) 0.0783(16) Uani 1 1 d . . . H3 H 1.1663 0.0877 0.8588 0.094 Uiso 1 1 calc R . . C4 C 1.0863(2) 0.0677(4) 1.0667(15) 0.0766(15) Uani 1 1 d . . . H4 H 1.1094 0.0174 1.1665 0.092 Uiso 1 1 calc R . . C5 C 1.0170(2) 0.1007(4) 1.1047(10) 0.0647(15) Uani 1 1 d . . . H5 H 0.9943 0.0734 1.2312 0.078 Uiso 1 1 calc R . . C6 C 0.98154(19) 0.1756(3) 0.9507(9) 0.0534(10) Uani 1 1 d . . . C7 C 0.9056(2) 0.2013(3) 0.9975(8) 0.0542(11) Uani 1 1 d . . . H7A H 0.8802 0.1248 0.9905 0.065 Uiso 1 1 calc R . . H7B H 0.9015 0.2322 1.1473 0.065 Uiso 1 1 calc R . . C8 C 0.81770(16) 0.2557(3) 0.7079(9) 0.0530(11) Uani 1 1 d . . . C9 C 0.85692(16) 0.4491(3) 0.5954(9) 0.0499(11) Uani 1 1 d . . . C10 C 0.91239(16) 0.3834(3) 0.7380(8) 0.0472(9) Uani 1 1 d . . . H10 H 0.9328 0.4395 0.8462 0.057 Uiso 1 1 calc R . . C11 C 0.8838(2) 0.5070(4) 0.3840(11) 0.0676(13) Uani 1 1 d . . . H11A H 0.8459 0.5451 0.3069 0.081 Uiso 1 1 calc R . . H11B H 0.9041 0.4453 0.2918 0.081 Uiso 1 1 calc R . . H11C H 0.9182 0.5673 0.4196 0.081 Uiso 1 1 calc R . . C12 C 0.8194(2) 0.5447(4) 0.7384(11) 0.0703(14) Uani 1 1 d . . . H12A H 0.8030 0.5070 0.8719 0.084 Uiso 1 1 calc R . . H12B H 0.7806 0.5775 0.6578 0.084 Uiso 1 1 calc R . . H12C H 0.8511 0.6094 0.7749 0.084 Uiso 1 1 calc R . . C13 C 0.7544(2) 0.3493(4) 0.3927(12) 0.0685(13) Uani 1 1 d . . . H13A H 0.7603 0.4191 0.2984 0.082 Uiso 1 1 calc R . . H13B H 0.7109 0.3557 0.4697 0.082 Uiso 1 1 calc R . . H13C H 0.7546 0.2763 0.3048 0.082 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 0.0342(4) 0.0503(5) 0.0817(7) 0.0058(6) 0.0077(6) 0.0032(3) O1 0.0471(14) 0.0493(15) 0.128(3) 0.007(2) 0.003(2) -0.0196(12) N1 0.0317(12) 0.0359(13) 0.076(2) 0.0010(15) 0.0073(16) -0.0022(10) N2 0.0347(12) 0.0383(14) 0.094(3) 0.001(2) -0.010(2) -0.0055(10) C1 0.0330(16) 0.0361(16) 0.084(3) -0.001(2) -0.001(2) -0.0012(12) C2 0.0361(17) 0.052(2) 0.110(4) -0.003(3) 0.004(3) 0.0053(15) C3 0.0414(19) 0.062(2) 0.131(5) -0.006(3) -0.005(3) 0.0120(18) C4 0.056(2) 0.054(2) 0.120(4) 0.004(4) -0.022(4) 0.0083(18) C5 0.057(2) 0.046(2) 0.091(4) 0.005(2) -0.008(3) 0.0083(17) C6 0.0404(18) 0.0378(18) 0.082(3) -0.004(2) 0.000(2) 0.0001(14) C7 0.0439(18) 0.0429(17) 0.076(3) 0.0030(19) 0.0053(19) 0.0041(14) C8 0.0321(14) 0.0440(18) 0.083(3) 0.000(2) 0.008(2) -0.0026(14) C9 0.0325(14) 0.0328(15) 0.084(3) 0.0006(19) -0.0047(19) -0.0028(11) C10 0.0312(14) 0.0339(15) 0.077(3) -0.0006(19) 0.0013(18) -0.0029(12) C11 0.050(2) 0.053(2) 0.101(4) 0.014(3) -0.003(3) -0.0016(17) C12 0.058(2) 0.0463(19) 0.107(4) -0.016(3) -0.011(3) 0.0149(17) C13 0.0407(18) 0.064(2) 0.101(4) 0.001(3) -0.015(3) -0.0074(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 S1 C1 1.786(5) . ? S1 C10 1.855(4) . ? O1 C8 1.228(4) . ? N1 C8 1.399(5) . ? N1 C10 1.452(5) . ? N1 C7 1.458(5) . ? N2 C8 1.364(7) . ? N2 C13 1.448(7) . ? N2 C9 1.472(4) . ? C1 C6 1.401(7) . ? C1 C2 1.415(5) . ? C2 C3 1.383(8) . ? C2 H2 0.9300 . ? C3 C4 1.372(10) . ? C3 H3 0.9300 . ? C4 C5 1.399(6) . ? C4 H4 0.9300 . ? C5 C6 1.416(7) . ? C5 H5 0.9300 . ? C6 C7 1.514(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C11 1.518(7) . ? C9 C12 1.538(6) . ? C9 C10 1.548(5) . ? C10 H10 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 S1 C10 96.2(2) . . ? C8 N1 C10 107.7(4) . . ? C8 N1 C7 122.5(3) . . ? C10 N1 C7 121.6(3) . . ? C8 N2 C13 123.9(3) . . ? C8 N2 C9 111.7(4) . . ? C13 N2 C9 122.9(4) . . ? C6 C1 C2 119.6(5) . . ? C6 C1 S1 124.8(3) . . ? C2 C1 S1 115.6(4) . . ? C3 C2 C1 119.6(6) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 121.5(4) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 119.9(6) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.0(6) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 119.3(3) . . ? C1 C6 C7 124.0(4) . . ? C5 C6 C7 116.7(4) . . ? N1 C7 C6 115.0(4) . . ? N1 C7 H7A 108.5 . . ? C6 C7 H7A 108.5 . . ? N1 C7 H7B 108.5 . . ? C6 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? O1 C8 N2 127.7(5) . . ? O1 C8 N1 124.2(5) . . ? N2 C8 N1 108.1(3) . . ? N2 C9 C11 112.2(5) . . ? N2 C9 C12 110.4(3) . . ? C11 C9 C12 110.4(4) . . ? N2 C9 C10 98.9(3) . . ? C11 C9 C10 115.4(3) . . ? C12 C9 C10 109.0(4) . . ? N1 C10 C9 103.0(3) . . ? N1 C10 S1 110.7(2) . . ? C9 C10 S1 110.1(3) . . ? N1 C10 H10 110.9 . . ? C9 C10 H10 110.9 . . ? S1 C10 H10 110.9 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C10 S1 C1 C6 23.8(4) . . . . ? C10 S1 C1 C2 -155.9(4) . . . . ? C6 C1 C2 C3 -0.9(7) . . . . ? S1 C1 C2 C3 178.9(4) . . . . ? C1 C2 C3 C4 0.4(8) . . . . ? C2 C3 C4 C5 -0.5(9) . . . . ? C3 C4 C5 C6 1.1(8) . . . . ? C2 C1 C6 C5 1.4(6) . . . . ? S1 C1 C6 C5 -178.4(3) . . . . ? C2 C1 C6 C7 -176.6(4) . . . . ? S1 C1 C6 C7 3.6(6) . . . . ? C4 C5 C6 C1 -1.5(7) . . . . ? C4 C5 C6 C7 176.7(5) . . . . ? C8 N1 C7 C6 116.5(4) . . . . ? C10 N1 C7 C6 -28.1(5) . . . . ? C1 C6 C7 N1 -7.7(6) . . . . ? C5 C6 C7 N1 174.3(4) . . . . ? C13 N2 C8 O1 7.1(8) . . . . ? C9 N2 C8 O1 173.6(4) . . . . ? C13 N2 C8 N1 -172.9(4) . . . . ? C9 N2 C8 N1 -6.4(5) . . . . ? C10 N1 C8 O1 164.5(4) . . . . ? C7 N1 C8 O1 15.7(6) . . . . ? C10 N1 C8 N2 -15.5(4) . . . . ? C7 N1 C8 N2 -164.3(4) . . . . ? C8 N2 C9 C11 145.6(4) . . . . ? C13 N2 C9 C11 -47.7(6) . . . . ? C8 N2 C9 C12 -90.8(4) . . . . ? C13 N2 C9 C12 75.8(7) . . . . ? C8 N2 C9 C10 23.4(5) . . . . ? C13 N2 C9 C10 -169.9(4) . . . . ? C8 N1 C10 C9 29.6(4) . . . . ? C7 N1 C10 C9 178.7(4) . . . . ? C8 N1 C10 S1 -88.1(3) . . . . ? C7 N1 C10 S1 61.0(5) . . . . ? N2 C9 C10 N1 -30.8(4) . . . . ? C11 C9 C10 N1 -150.6(4) . . . . ? C12 C9 C10 N1 84.6(4) . . . . ? N2 C9 C10 S1 87.4(3) . . . . ? C11 C9 C10 S1 -32.4(4) . . . . ? C12 C9 C10 S1 -157.3(3) . . . . ? C1 S1 C10 N1 -51.4(3) . . . . ? C1 S1 C10 C9 -164.7(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.92 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.404 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.050