# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_11 _database_code_CSD 175467 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Sackus, Algirdas' 'Brickute, Diana' 'Romming, Christian' 'Slok, Frank A.' _publ_contact_author_name 'Prof Algirdas Sackus' _publ_contact_author_address ; Department of Organic Chemistry Kaunas University of Technology Radvilenu pl. 19 Kaunas LT-3028 LITHUANIA ; _publ_contact_author_email 'ASACKUS@CTF.KTU.LT' _publ_section_title ; Facile synthesis of 2-substited ethyl 2-(2-amino-5-ethoxycarbonylthiazol-4-yl)ethanoates ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ethyl 2-[5-ethoxycarbonyl-2-(1-pyrrolo)thiazol-4-yl]-2-iminoethanoate ; _chemical_name_common ? _chemical_melting_point 138-140 _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N3 O4 S' _chemical_formula_weight 321.35 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 ? _symmetry_space_group_name_H-M P2(1)/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 7.7843(11) _cell_length_b 15.848(2) _cell_length_c 13.0532(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.416(4) _cell_angle_gamma 90.00 _cell_volume 1566.4(4) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type SADABS _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 0.71073 _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26718 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 6.85 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3821 _reflns_number_gt 2744 _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^)+(0.0520P)^2^+0.4000P] 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 3821 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.062 _refine_ls_shift/su_mean 0.004 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 0.24363(6) 0.51600(3) -0.03466(3) 0.04816(14) Uani 1 1 d . . . O1 O 0.1745(2) 0.34750(9) 0.17469(10) 0.0704(4) Uani 1 1 d . . . O2 O 0.11470(17) 0.34557(8) -0.00330(9) 0.0571(3) Uani 1 1 d . . . O3 O 0.2761(2) 0.47664(12) 0.43362(11) 0.0797(5) Uani 1 1 d . . . O4 O 0.10698(18) 0.53524(10) 0.28863(10) 0.0671(4) Uani 1 1 d . . . N1 N 0.40209(18) 0.58956(9) 0.13894(10) 0.0458(3) Uani 1 1 d . . . N2 N 0.39857(18) 0.67125(9) -0.01315(10) 0.0476(3) Uani 1 1 d . . . N3 N 0.5417(2) 0.46033(14) 0.32016(14) 0.0719(5) Uani 1 1 d . . . H3 H 0.552(3) 0.4532(15) 0.388(2) 0.074(7) Uiso 1 1 d . . . C1 C 0.2566(2) 0.46336(11) 0.08373(12) 0.0462(4) Uani 1 1 d . . . C2 C 0.3447(2) 0.51201(11) 0.16501(12) 0.0446(3) Uani 1 1 d . . . C3 C 0.3577(2) 0.59897(10) 0.03654(12) 0.0434(3) Uani 1 1 d . . . C4 C 0.3623(3) 0.68611(14) -0.12078(15) 0.0615(5) Uani 1 1 d . . . H4 H 0.309(3) 0.6440(16) -0.1643(19) 0.079(7) Uiso 1 1 d . . . C5 C 0.4171(3) 0.76495(14) -0.13620(17) 0.0669(5) Uani 1 1 d . . . H5 H 0.413(3) 0.7920(16) -0.204(2) 0.091(7) Uiso 1 1 d . . . C6 C 0.4919(3) 0.80042(14) -0.03633(17) 0.0647(5) Uani 1 1 d . . . H6 H 0.544(3) 0.8537(16) -0.0227(17) 0.076(7) Uiso 1 1 d . . . C7 C 0.4798(3) 0.74267(12) 0.03816(16) 0.0586(5) Uani 1 1 d . . . H7 H 0.520(3) 0.7431(14) 0.1149(19) 0.073(6) Uiso 1 1 d . . . C8 C 0.1792(2) 0.37974(11) 0.09160(13) 0.0508(4) Uani 1 1 d . . . C9 C 0.0380(3) 0.26131(13) -0.00270(18) 0.0633(5) Uani 1 1 d . . . H9A H -0.057(3) 0.2642(15) 0.0371(19) 0.077(7) Uiso 1 1 d . . . H9B H 0.134(3) 0.2223(15) 0.0316(19) 0.079(7) Uiso 1 1 d . . . C10 C -0.0336(5) 0.2351(2) -0.1139(2) 0.0886(8) Uani 1 1 d . . . H10A H -0.115(5) 0.281(2) -0.153(3) 0.129(12) Uiso 1 1 d . . . H10B H 0.070(4) 0.2249(19) -0.146(2) 0.108(10) Uiso 1 1 d . . . H10C H -0.087(4) 0.180(2) -0.118(2) 0.108(9) Uiso 1 1 d . . . C11 C 0.3891(2) 0.48708(11) 0.27900(12) 0.0494(4) Uani 1 1 d . . . C12 C 0.2508(2) 0.49794(12) 0.34326(13) 0.0542(4) Uani 1 1 d . . . C13 C -0.0370(4) 0.5503(3) 0.3443(3) 0.0907(9) Uani 1 1 d . . . H13A H -0.074(4) 0.494(2) 0.338(2) 0.105(11) Uiso 1 1 d . . . H13B H 0.021(5) 0.578(2) 0.411(3) 0.140(13) Uiso 1 1 d . . . C14 C -0.1551(4) 0.6147(2) 0.2857(2) 0.0816(7) Uani 1 1 d . . . H14A H -0.076(5) 0.667(3) 0.301(3) 0.142(12) Uiso 1 1 d . . . H14B H -0.261(5) 0.623(2) 0.323(3) 0.124(10) Uiso 1 1 d . . . H14C H -0.204(5) 0.600(2) 0.209(3) 0.137(12) 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 S1 0.0563(3) 0.0507(2) 0.0357(2) -0.00191(16) 0.00712(16) -0.00053(18) O1 0.0898(10) 0.0689(9) 0.0526(7) 0.0091(6) 0.0166(7) -0.0123(7) O2 0.0681(8) 0.0501(7) 0.0506(7) 0.0001(5) 0.0087(6) -0.0065(6) O3 0.0809(10) 0.1145(13) 0.0467(7) 0.0240(8) 0.0207(7) 0.0234(9) O4 0.0585(8) 0.0961(10) 0.0485(7) 0.0134(7) 0.0164(6) 0.0205(7) N1 0.0493(7) 0.0507(7) 0.0368(6) -0.0012(5) 0.0088(5) 0.0012(6) N2 0.0549(8) 0.0476(7) 0.0405(7) 0.0003(6) 0.0115(6) 0.0000(6) N3 0.0564(9) 0.1067(15) 0.0505(9) 0.0186(9) 0.0081(8) 0.0123(9) C1 0.0480(9) 0.0518(9) 0.0385(8) 0.0010(6) 0.0096(6) 0.0032(7) C2 0.0431(8) 0.0530(9) 0.0381(7) 0.0019(6) 0.0100(6) 0.0052(7) C3 0.0421(8) 0.0491(8) 0.0391(7) -0.0017(6) 0.0099(6) 0.0048(6) C4 0.0807(13) 0.0623(12) 0.0408(9) 0.0016(8) 0.0127(9) -0.0064(10) C5 0.0838(14) 0.0659(12) 0.0530(11) 0.0117(9) 0.0202(10) -0.0036(10) C6 0.0753(13) 0.0544(11) 0.0675(12) 0.0024(9) 0.0228(10) -0.0088(10) C7 0.0682(12) 0.0565(11) 0.0509(10) -0.0054(8) 0.0137(9) -0.0076(9) C8 0.0500(9) 0.0536(9) 0.0481(9) 0.0027(7) 0.0101(7) 0.0034(7) C9 0.0663(13) 0.0515(11) 0.0706(13) 0.0019(9) 0.0130(10) -0.0068(9) C10 0.109(2) 0.0718(16) 0.0801(17) -0.0163(13) 0.0121(16) -0.0217(16) C11 0.0508(9) 0.0568(9) 0.0388(8) 0.0036(7) 0.0070(7) 0.0001(7) C12 0.0575(10) 0.0643(11) 0.0400(8) 0.0052(7) 0.0099(7) 0.0048(8) C13 0.0764(16) 0.119(3) 0.0876(19) 0.0233(18) 0.0407(15) 0.0252(17) C14 0.0721(15) 0.0967(19) 0.0736(15) -0.0209(13) 0.0117(12) 0.0151(14) _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 C3 1.7314(16) . ? S1 C1 1.7385(16) . ? O1 C8 1.207(2) . ? O2 C8 1.338(2) . ? O2 C9 1.464(2) . ? O3 C12 1.198(2) . ? O4 C12 1.319(2) . ? O4 C13 1.489(3) . ? N1 C3 1.309(2) . ? N1 C2 1.377(2) . ? N2 C4 1.387(2) . ? N2 C3 1.389(2) . ? N2 C7 1.390(2) . ? N3 C11 1.258(2) . ? N3 H3 0.88(2) . ? C1 C2 1.361(2) . ? C1 C8 1.469(3) . ? C2 C11 1.500(2) . ? C4 C5 1.350(3) . ? C4 H4 0.91(2) . ? C5 C6 1.415(3) . ? C5 H5 0.98(3) . ? C6 C7 1.354(3) . ? C6 H6 0.94(3) . ? C7 H7 0.98(2) . ? C9 C10 1.488(3) . ? C9 H9A 1.00(2) . ? C9 H9B 0.99(3) . ? C10 H10A 1.02(4) . ? C10 H10B 1.01(3) . ? C10 H10C 0.97(3) . ? C11 C12 1.520(2) . ? C13 C14 1.464(4) . ? C13 H13A 0.94(3) . ? C13 H13B 0.99(4) . ? C14 H14A 1.03(4) . ? C14 H14B 1.06(4) . ? C14 H14C 1.02(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 C3 S1 C1 88.31(8) . . ? C8 O2 C9 115.49(14) . . ? C12 O4 C13 116.65(16) . . ? C3 N1 C2 109.27(13) . . ? C4 N2 C3 126.71(15) . . ? C4 N2 C7 108.22(15) . . ? C3 N2 C7 125.05(14) . . ? C11 N3 H3 109.0(15) . . ? C2 C1 C8 126.67(15) . . ? C2 C1 S1 109.62(13) . . ? C8 C1 S1 123.70(12) . . ? C1 C2 N1 116.53(14) . . ? C1 C2 C11 125.61(15) . . ? N1 C2 C11 117.83(14) . . ? N1 C3 N2 122.40(14) . . ? N1 C3 S1 116.26(12) . . ? N2 C3 S1 121.34(11) . . ? C5 C4 N2 108.10(18) . . ? C5 C4 H4 134.3(15) . . ? N2 C4 H4 117.6(15) . . ? C4 C5 C6 107.88(18) . . ? C4 C5 H5 126.4(15) . . ? C6 C5 H5 125.6(15) . . ? C7 C6 C5 108.10(19) . . ? C7 C6 H6 124.9(14) . . ? C5 C6 H6 127.0(14) . . ? C6 C7 N2 107.70(18) . . ? C6 C7 H7 132.2(14) . . ? N2 C7 H7 120.1(14) . . ? O1 C8 O2 125.24(17) . . ? O1 C8 C1 122.90(16) . . ? O2 C8 C1 111.86(14) . . ? O2 C9 C10 108.10(19) . . ? O2 C9 H9A 108.2(14) . . ? C10 C9 H9A 111.5(14) . . ? O2 C9 H9B 107.9(14) . . ? C10 C9 H9B 109.8(14) . . ? H9A C9 H9B 111(2) . . ? C9 C10 H10A 109.6(19) . . ? C9 C10 H10B 107.3(17) . . ? H10A C10 H10B 112(3) . . ? C9 C10 H10C 111.4(18) . . ? H10A C10 H10C 114(3) . . ? H10B C10 H10C 102(2) . . ? N3 C11 C2 119.29(16) . . ? N3 C11 C12 121.46(16) . . ? C2 C11 C12 119.21(14) . . ? O3 C12 O4 125.68(17) . . ? O3 C12 C11 122.37(16) . . ? O4 C12 C11 111.92(14) . . ? C14 C13 O4 108.0(2) . . ? C14 C13 H13A 119(2) . . ? O4 C13 H13A 93(2) . . ? C14 C13 H13B 105(2) . . ? O4 C13 H13B 105(2) . . ? H13A C13 H13B 125(3) . . ? C13 C14 H14A 101(2) . . ? C13 C14 H14B 108.2(18) . . ? H14A C14 H14B 108(3) . . ? C13 C14 H14C 113(2) . . ? H14A C14 H14C 117(3) . . ? H14B C14 H14C 109(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.252 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.034