# Perkin Transactions I © The Royal Society of Chemistry, 1999 # CCDC Number: 207/344 #======================================================================= data_kaju #======================================================================= _publ_section_title ; Catalytic Enantioselective Formation of Aziridines from \a-Imino Esters ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name 'Karsten Juhl ' 'Rita G. Hazell ' 'Karl Anker Jrgensen ' _publ_author_address ; Center for Metal Catalysed Reactions Department of Chemistry Aarhus University Langelandsgade 140 DK-8000 \%Arhus C Denmark ; #======================================================================= _publ_section_references ; Becker,P.J. & Coppens, P. (1974). Acta Cryst. A30, 129-153. Burnett,M.N. & Johnson,C.K. (1996). ORTEP-III. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Busing,W.R., Martin,K.O. & Levy,H.A. (1962). ORFLS. Report ORNL-TM-305. Oak Ridge National Laboratory, Tennessee, USA. Cascarano,G., Altomare,A.,Giacovazzo,C., Guagliardi,A., Moliterni,A.G.G, Siliqi,D., Burla,M.C., Polidori,G. & Camalli,M. (1996). Acta Cryst. A52. C-50. Hazell,A. (1995). KRYSTAL, An integrated system of crystallographic programs. Aarhus University, Denmark. Rogers,D. (1981). Acta Cryst. A37, 734-741. Siemens (1995) SMART, SAINT and XPREP Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA. ; #======================================================================= # 5. CHEMICAL DATA _chemical_formula_sum C12H15NO4S _chemical_formula_weight 269.33 #================================== # 6. CRYSTAL DATA _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 8.195(1) _cell_length_b 9.437(2) _cell_length_c 9.663(2) _cell_angle_alpha 98.890(3) _cell_angle_beta 105.927(3) _cell_angle_gamma 106.060(3) _cell_volume 668.7(1) _cell_formula_units_Z 2 _cell_measurement_temperature 120 _cell_measurement_reflns_used 4383 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 30.8 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.34 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.99 #================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation scans with narrow fram' _diffrn_reflns_number 8344 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.3 _diffrn_reflns_theta_max 30.8 _diffrn_reflns_reduction_process 8344 _reflns_number_total 3815 _reflns_number_observed 2859 _reflns_observed_criterion I>3\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Cascarano et al., 1996) KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme ; 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^-|F|}^2^ ; _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method ; Type 1 Lorentzian isotropic (1974)Becker-Coppens ; _refine_ls_extinction_coef 32(7) _refine_ls_number_reflns 2859 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_obs 0.033 _refine_ls_wR_factor_obs 0.042 _refine_ls_goodness_of_fit_obs 1.36 _refine_ls_shift/esd_max 0.0003 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_max 0.51(4) _refine_diff_density_min -0.38(4) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type S 0.21511(5) 0.23493(4) 0.57912(4) 0.0204(2) Uij O(1) 0.1513(2) -0.0300(1) 0.8852(1) 0.0374(8) Uij O(2) 0.3868(1) 0.1260(1) 1.0812(1) 0.0270(7) Uij O(3) 0.3883(1) 0.3329(1) 0.5889(1) 0.0255(6) Uij O(4) 0.1004(1) 0.1278(1) 0.4406(1) 0.0263(6) Uij N(1) 0.2443(2) 0.1299(1) 0.6974(1) 0.0217(7) Uij C(1) 0.3456(2) 0.1891(2) 0.8502(2) 0.0221(8) Uij C(2) 0.4799(2) 0.3206(2) 0.9117(2) 0.0335(10) Uij C(3) 0.2825(2) 0.0831(2) 0.9389(2) 0.0236(8) Uij C(4) 0.3291(2) 0.0294(2) 1.1752(2) 0.0315(10) Uij C(5) 0.4680(3) 0.0945(2) 1.3267(2) 0.0360(12) Uij C(6) 0.0987(2) 0.3484(1) 0.6398(1) 0.0201(8) Uij C(7) -0.0729(2) 0.2779(2) 0.6430(2) 0.0288(9) Uij C(8) -0.1639(2) 0.3667(2) 0.6922(2) 0.0320(10) Uij C(9) -0.0867(2) 0.5251(2) 0.7394(2) 0.0271(9) Uij C(10) 0.0839(2) 0.5927(2) 0.7335(2) 0.0279(9) Uij C(11) 0.1775(2) 0.5057(2) 0.6841(2) 0.0246(9) Uij C(12) -0.1864(3) 0.6203(2) 0.7957(3) 0.0387(13) Uij H(N) 0.158(3) 0.057(2) 0.681(2) 0.046(6) Uiso H(2a) 0.542(2) 0.352(2) 1.022(2) 0.036(5) Uiso H(2b) 0.513(2) 0.383(2) 0.851(2) 0.044(5) Uiso H(4a) 0.323(2) -0.072(2) 1.132(2) 0.033(4) Uiso H(4b) 0.211(2) 0.032(2) 1.177(2) 0.039(5) Uiso H(5a) 0.477(2) 0.199(2) 1.370(2) 0.047(6) Uiso H(5b) 0.584(3) 0.092(2) 1.327(2) 0.050(6) Uiso H(5c) 0.439(3) 0.034(2) 1.393(2) 0.054(6) Uiso H(7) -0.124(2) 0.169(2) 0.606(2) 0.046(5) Uiso H(8) -0.280(3) 0.319(2) 0.694(2) 0.048(6) Uiso H(10) 0.138(2) 0.702(2) 0.768(2) 0.036(5) Uiso H(11) 0.288(2) 0.549(2) 0.678(2) 0.027(4) Uiso H(12a) -0.179(3) 0.612(2) 0.898(2) 0.052(6) Uiso H(12b) -0.136(3) 0.721(3) 0.795(2) 0.065(7) Uiso H(12c) -0.315(3) 0.589(2) 0.734(2) 0.056(6) Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S 0.0193(2) 0.0200(2) 0.0182(2) 0.0030(1) 0.0059(1) 0.0015(1) O(1) 0.0432(7) 0.0250(6) 0.0278(6) -0.0029(5) 0.0019(5) 0.0062(5) O(2) 0.0296(5) 0.0288(5) 0.0193(5) 0.0078(4) 0.0052(4) 0.0058(4) O(3) 0.0198(5) 0.0273(5) 0.0265(6) 0.0023(4) 0.0108(4) 0.0030(4) O(4) 0.0287(5) 0.0244(5) 0.0175(5) 0.0014(4) 0.0054(4) -0.0001(4) N(1) 0.0216(6) 0.0191(6) 0.0196(6) 0.0042(5) 0.0038(5) 0.0015(5) C(1) 0.0211(6) 0.0240(7) 0.0197(7) 0.0085(6) 0.0055(5) 0.0017(5) C(2) 0.0322(8) 0.0334(9) 0.0229(8) -0.0016(7) 0.0048(7) 0.0048(7) C(3) 0.0267(7) 0.0215(7) 0.0215(7) 0.0106(6) 0.0056(6) 0.0022(5) C(4) 0.0414(9) 0.0288(8) 0.0280(8) 0.0146(7) 0.0117(7) 0.0124(7) C(5) 0.0418(10) 0.0472(11) 0.0256(8) 0.0231(9) 0.0111(7) 0.0130(8) C(6) 0.0180(6) 0.0202(6) 0.0205(7) 0.0054(5) 0.0054(5) 0.0044(5) C(7) 0.0207(7) 0.0179(7) 0.0434(9) 0.0014(6) 0.0109(6) 0.0047(6) C(8) 0.0211(7) 0.0232(7) 0.0518(11) 0.0037(6) 0.0166(7) 0.0080(7) C(9) 0.0244(7) 0.0216(7) 0.0372(9) 0.0081(6) 0.0123(6) 0.0082(6) C(10) 0.0260(7) 0.0175(7) 0.0365(9) 0.0030(6) 0.0103(6) 0.0049(6) C(11) 0.0194(7) 0.0201(7) 0.0306(8) 0.0009(5) 0.0092(6) 0.0048(6) C(12) 0.0347(9) 0.0246(8) 0.0642(13) 0.0119(7) 0.0264(9) 0.0103(8) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S O(3) 1.433(1) S O(4) 1.436(1) S N(1) 1.636(1) S C(6) 1.755(1) O(1) C(3) 1.206(2) O(2) C(3) 1.332(2) O(2) C(4) 1.461(2) N(1) C(1) 1.413(2) C(1) C(2) 1.327(2) C(1) C(3) 1.492(2) C(4) C(5) 1.495(2) C(6) C(11) 1.388(2) C(6) C(7) 1.390(2) C(7) C(8) 1.379(2) C(8) C(9) 1.397(2) C(9) C(10) 1.388(2) C(9) C(12) 1.506(2) C(10) C(11) 1.385(2) N(1) H(N) 0.792(20) C(2) H(2a) 0.999(18) C(2) H(2b) 0.928(20) C(4) H(4a) 0.962(18) C(4) H(4b) 0.979(19) C(5) H(5a) 0.986(20) C(5) H(5b) 0.955(21) C(5) H(5c) 0.959(21) C(7) H(7) 0.964(20) C(8) H(8) 0.938(19) C(10) H(10) 0.962(18) C(11) H(11) 0.909(16) C(12) H(12a) 0.984(21) C(12) H(12b) 0.924(24) C(12) H(12c) 0.991(21) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O(3) S O(4) 119.30(6) O(3) S N(1) 108.43(7) O(3) S C(6) 108.27(6) O(4) S N(1) 104.48(6) O(4) S C(6) 109.56(7) N(1) S C(6) 105.99(7) C(3) O(2) C(4) 115.8(1) S N(1) C(1) 124.0(1) N(1) C(1) C(2) 126.4(1) C(2) C(1) C(3) 122.6(1) N(1) C(1) C(3) 111.0(1) O(1) C(3) O(2) 124.3(1) O(1) C(3) C(1) 122.6(1) O(2) C(3) C(1) 113.1(1) O(2) C(4) C(5) 106.6(1) C(7) C(6) C(11) 120.9(1) S C(6) C(11) 120.3(1) S C(6) C(7) 118.9(1) C(6) C(7) C(8) 119.0(1) C(7) C(8) C(9) 121.4(1) C(8) C(9) C(10) 118.5(1) C(10) C(9) C(12) 120.8(1) C(8) C(9) C(12) 120.7(1) C(9) C(10) C(11) 121.1(1) C(6) C(11) C(10) 119.2(1) C(1) N(1) H(N) 113.5(15) S N(1) H(N) 113.0(15) H(2a) C(2) H(2b) 121.1(15) C(1) C(2) H(2b) 119.1(12) C(1) C(2) H(2a) 119.8(10) H(4a) C(4) H(4b) 111.1(15) O(2) C(4) H(4a) 106.9(11) C(5) C(4) H(4a) 112.1(11) O(2) C(4) H(4b) 108.6(11) C(5) C(4) H(4b) 111.2(11) H(5b) C(5) H(5c) 104.5(16) H(5a) C(5) H(5b) 110.1(16) C(4) C(5) H(5b) 112.0(12) H(5a) C(5) H(5c) 107.2(16) C(4) C(5) H(5c) 110.5(12) C(4) C(5) H(5a) 112.3(11) C(8) C(7) H(7) 123.6(11) C(6) C(7) H(7) 117.4(11) C(7) C(8) H(8) 119.0(12) C(9) C(8) H(8) 119.6(12) C(11) C(10) H(10) 120.3(10) C(9) C(10) H(10) 118.5(10) C(10) C(11) H(11) 121.9(10) C(6) C(11) H(11) 118.8(10) H(12a) C(12) H(12b) 110.0(18) H(12b) C(12) H(12c) 105.7(18) C(9) C(12) H(12b) 110.4(14) H(12a) C(12) H(12c) 108.9(17) C(9) C(12) H(12a) 108.3(12) C(9) C(12) H(12c) 113.5(12) loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A N(1) H(N) O(4) 0.792(20) 2.208(21) 2.967(2) 160.5(20) 2_556