# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_cd21148 _database_code_CSD 177332 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Yu-Mei Luo' 'Li-Xin Dai' 'Xue Long Hou' _publ_contact_author_name 'Prof Xue Long Hou' _publ_contact_author_address ; State Key Laboratory of Organometallic Chemistry Shanghai Institution of Organic Chemistry 354 Fenglin Road Shanghai 200032 CHINA ; _publ_contact_author_email 'XLHOU@PUB.SIOC.AC.CN' _publ_section_title ; Reaction of a-Carbanion of Imines with N-Tosylimines: A Facile Route to b-Amino Aldehydes and 1,3-Diamines ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 N O3 S' _chemical_formula_weight 345.44 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4619(11) _cell_length_b 9.8687(12) _cell_length_c 10.1330(12) _cell_angle_alpha 100.097(2) _cell_angle_beta 99.529(2) _cell_angle_gamma 91.423(2) _cell_volume 917.26(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 588 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 18.85 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0,2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.4627 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 4855 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.1439 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3371 _reflns_number_gt 1338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0055P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3371 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1172 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0610 _refine_ls_wR_factor_gt 0.0507 _refine_ls_goodness_of_fit_ref 0.646 _refine_ls_restrained_S_all 0.646 _refine_ls_shift/su_max 0.097 _refine_ls_shift/su_mean 0.006 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 S S 0.67656(9) 0.82644(8) 0.64633(7) 0.0571(2) Uani 1 1 d . . . O1 O 0.53162(19) 0.81429(19) 0.57379(16) 0.0718(6) Uani 1 1 d . . . O2 O 0.7184(2) 0.93171(18) 0.76489(17) 0.0715(6) Uani 1 1 d . . . O3 O 0.8998(2) 1.1542(2) 0.43714(17) 0.0695(6) Uani 1 1 d . . . N N 0.7767(3) 0.8528(3) 0.5373(2) 0.0552(7) Uani 1 1 d . . . C1 C 0.7286(3) 0.8231(3) 0.3881(3) 0.0513(8) Uani 1 1 d . . . C2 C 0.8183(3) 0.9229(3) 0.3314(2) 0.0473(8) Uani 1 1 d . . . C3 C 0.7793(3) 0.9119(3) 0.1759(3) 0.0556(8) Uani 1 1 d . . . C4 C 0.6272(4) 0.9485(6) 0.1279(4) 0.0844(13) Uani 1 1 d . . . C5 C 0.8871(5) 0.9968(5) 0.1252(4) 0.0749(12) Uani 1 1 d . . . C6 C 0.8020(4) 1.0680(3) 0.4016(3) 0.0573(9) Uani 1 1 d . . . C7 C 0.7362(3) 0.6737(3) 0.3241(3) 0.0518(8) Uani 1 1 d . . . C8 C 0.8584(4) 0.6036(4) 0.3463(3) 0.0648(9) Uani 1 1 d . . . C9 C 0.8624(5) 0.4667(4) 0.2886(4) 0.0832(11) Uani 1 1 d . . . C10 C 0.7422(6) 0.3995(5) 0.2077(4) 0.0939(14) Uani 1 1 d . . . C11 C 0.6206(5) 0.4677(5) 0.1831(4) 0.0880(13) Uani 1 1 d . . . C12 C 0.6167(4) 0.6042(4) 0.2400(3) 0.0698(10) Uani 1 1 d . . . C13 C 0.7181(3) 0.6690(3) 0.6966(3) 0.0475(7) Uani 1 1 d . . . C14 C 0.7832(3) 0.6669(4) 0.8287(3) 0.0650(9) Uani 1 1 d . . . C15 C 0.8145(4) 0.5438(4) 0.8687(4) 0.0768(11) Uani 1 1 d . . . C16 C 0.7844(3) 0.4197(3) 0.7808(4) 0.0671(9) Uani 1 1 d . . . C17 C 0.7196(4) 0.4239(4) 0.6493(4) 0.0692(10) Uani 1 1 d . . . C18 C 0.6860(3) 0.5459(4) 0.6070(3) 0.0630(9) Uani 1 1 d . . . C19 C 0.8198(3) 0.2852(3) 0.8248(3) 0.1068(12) Uani 1 1 d . . . H20 H 0.9204 0.2720 0.8273 0.160 Uiso 1 1 calc R . . H21 H 0.7650 0.2112 0.7615 0.160 Uiso 1 1 calc R . . H22 H 0.7969 0.2865 0.9138 0.160 Uiso 1 1 calc R . . H1 H 0.626(2) 0.851(2) 0.3791(18) 0.044(7) Uiso 1 1 d . . . H2 H 0.914(2) 0.908(2) 0.3552(17) 0.032(7) Uiso 1 1 d . . . H3 H 0.786(2) 0.810(2) 0.138(2) 0.053(8) Uiso 1 1 d . . . H4 H 0.552(3) 0.884(3) 0.154(3) 0.139(16) Uiso 1 1 d . . . H5 H 0.611(3) 0.930(3) 0.032(3) 0.104(12) Uiso 1 1 d . . . H6 H 0.614(4) 1.046(3) 0.164(3) 0.136(18) Uiso 1 1 d . . . H7 H 0.864(2) 0.986(2) 0.032(2) 0.056(8) Uiso 1 1 d . . . H8 H 0.886(3) 1.094(3) 0.167(2) 0.087(12) Uiso 1 1 d . . . H9 H 0.989(4) 0.974(3) 0.145(3) 0.144(17) Uiso 1 1 d . . . H10 H 0.695(2) 1.092(2) 0.422(2) 0.074(9) Uiso 1 1 d . . . H11 H 0.940(3) 0.652(2) 0.397(2) 0.072(10) Uiso 1 1 d . . . H12 H 0.949(3) 0.417(3) 0.311(2) 0.066(10) Uiso 1 1 d . . . H13 H 0.741(3) 0.307(3) 0.170(3) 0.083(12) Uiso 1 1 d . . . H14 H 0.539(3) 0.423(3) 0.124(2) 0.080(11) Uiso 1 1 d . . . H15 H 0.530(2) 0.658(2) 0.229(2) 0.061(9) Uiso 1 1 d . . . H16 H 0.807(2) 0.750(2) 0.894(2) 0.062(9) Uiso 1 1 d . . . H17 H 0.852(3) 0.543(3) 0.953(2) 0.086(12) Uiso 1 1 d . . . H18 H 0.701(2) 0.339(2) 0.589(2) 0.066(9) Uiso 1 1 d . . . H19 H 0.635(2) 0.555(2) 0.517(2) 0.065(9) Uiso 1 1 d . . . H23 H 0.860(3) 0.851(3) 0.566(2) 0.067(11) Uiso 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 S 0.0570(6) 0.0733(6) 0.0455(5) 0.0124(4) 0.0186(4) 0.0112(5) O1 0.0421(13) 0.1090(17) 0.0689(13) 0.0241(12) 0.0128(10) 0.0163(12) O2 0.1085(17) 0.0626(13) 0.0433(12) 0.0022(10) 0.0202(10) 0.0118(12) O3 0.0637(16) 0.0741(16) 0.0659(14) 0.0071(11) 0.0031(11) 0.0063(13) N 0.0439(19) 0.087(2) 0.0370(15) 0.0155(13) 0.0075(13) 0.0055(16) C1 0.042(2) 0.074(2) 0.0383(18) 0.0118(16) 0.0055(14) 0.0071(19) C2 0.039(2) 0.065(2) 0.0395(18) 0.0138(16) 0.0056(14) 0.0123(18) C3 0.062(2) 0.069(3) 0.0376(18) 0.0150(17) 0.0086(15) 0.015(2) C4 0.069(3) 0.126(4) 0.056(3) 0.028(3) -0.008(2) 0.020(3) C5 0.095(4) 0.094(3) 0.042(2) 0.024(2) 0.019(2) 0.009(3) C6 0.057(3) 0.075(3) 0.0403(18) 0.0136(18) 0.0069(16) 0.013(2) C7 0.048(2) 0.068(2) 0.0429(18) 0.0142(17) 0.0126(15) 0.001(2) C8 0.059(3) 0.066(3) 0.071(2) 0.011(2) 0.019(2) 0.001(2) C9 0.093(4) 0.070(3) 0.097(3) 0.025(2) 0.033(3) 0.021(3) C10 0.123(5) 0.063(3) 0.097(3) 0.007(3) 0.033(3) -0.009(3) C11 0.086(4) 0.092(4) 0.081(3) 0.016(3) 0.004(3) -0.024(3) C12 0.068(3) 0.080(3) 0.062(2) 0.014(2) 0.012(2) 0.000(3) C13 0.0488(19) 0.057(2) 0.0375(17) 0.0057(15) 0.0132(13) 0.0014(16) C14 0.074(3) 0.065(3) 0.054(2) 0.006(2) 0.0101(17) 0.008(2) C15 0.089(3) 0.079(3) 0.060(3) 0.018(3) 0.001(2) 0.010(2) C16 0.069(2) 0.058(2) 0.080(3) 0.015(2) 0.0252(18) 0.0091(19) C17 0.082(3) 0.060(3) 0.063(3) -0.003(2) 0.025(2) -0.011(2) C18 0.063(2) 0.075(3) 0.051(2) 0.011(2) 0.0142(17) -0.010(2) C19 0.125(3) 0.077(3) 0.127(3) 0.033(2) 0.030(2) 0.025(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 S O2 1.4366(16) . ? S O1 1.4362(17) . ? S N 1.619(2) . ? S C13 1.752(3) . ? O3 C6 1.205(3) . ? N C1 1.480(3) . ? C1 C7 1.512(4) . ? C1 C2 1.529(4) . ? C2 C6 1.507(4) . ? C2 C3 1.542(3) . ? C3 C5 1.512(4) . ? C3 C4 1.514(4) . ? C7 C8 1.368(4) . ? C7 C12 1.383(4) . ? C8 C9 1.379(4) . ? C9 C10 1.367(5) . ? C10 C11 1.356(5) . ? C11 C12 1.373(5) . ? C13 C18 1.377(3) . ? C13 C14 1.382(3) . ? C14 C15 1.371(4) . ? C15 C16 1.375(4) . ? C16 C17 1.380(4) . ? C16 C19 1.501(4) . ? C17 C18 1.375(4) . ? 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 O2 S O1 120.06(12) . . ? O2 S N 106.97(12) . . ? O1 S N 105.78(12) . . ? O2 S C13 106.60(12) . . ? O1 S C13 108.66(13) . . ? N S C13 108.34(13) . . ? C1 N S 124.0(2) . . ? N C1 C7 113.9(2) . . ? N C1 C2 105.7(2) . . ? C7 C1 C2 113.7(2) . . ? C6 C2 C1 109.0(2) . . ? C6 C2 C3 110.0(2) . . ? C1 C2 C3 113.6(2) . . ? C5 C3 C4 111.3(3) . . ? C5 C3 C2 110.3(3) . . ? C4 C3 C2 113.8(3) . . ? O3 C6 C2 123.6(3) . . ? C8 C7 C12 118.3(3) . . ? C8 C7 C1 122.2(3) . . ? C12 C7 C1 119.6(3) . . ? C7 C8 C9 121.2(4) . . ? C10 C9 C8 119.5(4) . . ? C11 C10 C9 120.1(4) . . ? C10 C11 C12 120.5(4) . . ? C11 C12 C7 120.4(4) . . ? C18 C13 C14 118.8(3) . . ? C18 C13 S 121.3(2) . . ? C14 C13 S 119.9(2) . . ? C15 C14 C13 120.1(3) . . ? C14 C15 C16 122.2(3) . . ? C15 C16 C17 116.9(3) . . ? C15 C16 C19 122.0(3) . . ? C17 C16 C19 121.1(3) . . ? C18 C17 C16 122.0(3) . . ? C17 C18 C13 120.0(3) . . ? 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 O2 S N C1 -146.9(2) . . . . ? O1 S N C1 -17.8(3) . . . . ? C13 S N C1 98.5(3) . . . . ? S N C1 C7 -81.9(3) . . . . ? S N C1 C2 152.6(2) . . . . ? N C1 C2 C6 -54.6(3) . . . . ? C7 C1 C2 C6 179.7(2) . . . . ? N C1 C2 C3 -177.7(2) . . . . ? C7 C1 C2 C3 56.7(3) . . . . ? C6 C2 C3 C5 66.4(4) . . . . ? C1 C2 C3 C5 -171.1(3) . . . . ? C6 C2 C3 C4 -59.5(4) . . . . ? C1 C2 C3 C4 63.0(4) . . . . ? C1 C2 C6 O3 139.5(3) . . . . ? C3 C2 C6 O3 -95.3(3) . . . . ? N C1 C7 C8 -52.0(4) . . . . ? C2 C1 C7 C8 69.2(3) . . . . ? N C1 C7 C12 128.2(3) . . . . ? C2 C1 C7 C12 -110.6(3) . . . . ? C12 C7 C8 C9 -1.2(4) . . . . ? C1 C7 C8 C9 179.0(3) . . . . ? C7 C8 C9 C10 0.0(5) . . . . ? C8 C9 C10 C11 0.9(6) . . . . ? C9 C10 C11 C12 -0.6(6) . . . . ? C10 C11 C12 C7 -0.6(5) . . . . ? C8 C7 C12 C11 1.5(5) . . . . ? C1 C7 C12 C11 -178.7(3) . . . . ? O2 S C13 C18 177.5(2) . . . . ? O1 S C13 C18 46.8(3) . . . . ? N S C13 C18 -67.7(3) . . . . ? O2 S C13 C14 -1.9(3) . . . . ? O1 S C13 C14 -132.6(2) . . . . ? N S C13 C14 112.9(2) . . . . ? C18 C13 C14 C15 -0.1(4) . . . . ? S C13 C14 C15 179.3(3) . . . . ? C13 C14 C15 C16 0.6(5) . . . . ? C14 C15 C16 C17 -0.5(5) . . . . ? C14 C15 C16 C19 179.5(3) . . . . ? C15 C16 C17 C18 -0.1(5) . . . . ? C19 C16 C17 C18 179.8(3) . . . . ? C16 C17 C18 C13 0.6(5) . . . . ? C14 C13 C18 C17 -0.5(4) . . . . ? S C13 C18 C17 -179.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.136 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.031