# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Sean Bew' _publ_contact_author_address ; Department of Chemical Sciences University of East Anglia University Plain Norwich NR4 7TJ UNITED KINGDOM ; _publ_contact_author_email S.BEW@UEA.AC.UK _publ_section_title ; Stereoselective synthesis of N-alkylaziridines from N-chloroamines ; loop_ _publ_author_name 'Sean Bew' 'D. L. Hughes' 'Vladimir Savic' 'Katy M. Soapi' 'Martin A. Wilson' data_katys9 _database_code_depnum_ccdc_archive 'CCDC 611802' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H23 N O3' _chemical_formula_structural 'an aziridine t-Bu ester' _chemical_formula_sum 'C16 H23 N O3' _chemical_formula_weight 277.35 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.6144(16) _cell_length_b 11.689(3) _cell_length_c 25.371(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1665.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 10 _exptl_crystal_description needle-plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.106 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _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 Mo-K\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD4 diffractometer' _diffrn_measurement_method 'scintillation counter; \w/\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '10000 s' _diffrn_standards_decay_% 8.9 _diffrn_reflns_number 1400 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0883 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 19.98 _reflns_number_total 1240 _reflns_number_gt 685 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'CAD4/EXPRESS (Enraf-Nonius, 1992)' _computing_cell_refinement 'CAD4/EXPRESS (Enraf-Nonius, 1992)' _computing_data_reduction 'CAD4 (Hursthouse, 1976)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1971)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0542P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(3) _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 -3(5) _refine_ls_number_reflns 1240 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _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 C11 C 0.8941(17) 0.6639(7) 0.6339(3) 0.060(2) Uani 1 1 d . . . C12 C 0.7124(15) 0.6941(7) 0.6013(3) 0.071(3) Uani 1 1 d . . . H12 H 0.5871 0.7363 0.6153 0.085 Uiso 1 1 calc R . . C13 C 0.7040(16) 0.6654(7) 0.5484(3) 0.069(3) Uani 1 1 d . . . H13 H 0.5762 0.6884 0.5276 0.083 Uiso 1 1 calc R . . C14 C 0.8867(18) 0.6026(7) 0.5270(3) 0.057(2) Uani 1 1 d . . . C15 C 1.0740(16) 0.5697(6) 0.5585(3) 0.065(2) Uani 1 1 d . . . H15 H 1.1998 0.5275 0.5447 0.077 Uiso 1 1 calc R . . C16 C 1.0710(17) 0.6014(7) 0.6119(3) 0.068(2) Uani 1 1 d . . . H16 H 1.1969 0.5783 0.6332 0.082 Uiso 1 1 calc R . . O14 O 0.9023(11) 0.5666(4) 0.4758(2) 0.0795(19) Uani 1 1 d . . . C141 C 0.7056(16) 0.5933(7) 0.4421(3) 0.089(3) Uani 1 1 d . . . H14A H 0.7003 0.6744 0.4362 0.133 Uiso 1 1 calc R . . H14B H 0.5600 0.5691 0.4585 0.133 Uiso 1 1 calc R . . H14C H 0.7245 0.5545 0.4090 0.133 Uiso 1 1 calc R . . C1 C 0.8994(17) 0.6978(9) 0.6909(3) 0.082(3) Uani 1 1 d . . . H1 H 1.0311 0.6575 0.7081 0.099 Uiso 1 1 calc R . . C10 C 0.933(2) 0.8237(10) 0.6987(3) 0.147(5) Uani 1 1 d . . . H10A H 0.9465 0.8399 0.7357 0.221 Uiso 1 1 calc R . . H10B H 0.7978 0.8639 0.6845 0.221 Uiso 1 1 calc R . . H10C H 1.0746 0.8481 0.6809 0.221 Uiso 1 1 calc R . . N1 N 0.6740(12) 0.6614(6) 0.7155(2) 0.067(2) Uani 1 1 d . . . C2 C 0.6971(16) 0.6347(7) 0.7724(3) 0.077(3) Uani 1 1 d . . . H2 H 0.8564 0.6436 0.7877 0.092 Uiso 1 1 calc R . . C21 C 0.4987(19) 0.6663(10) 0.8061(3) 0.082(3) Uani 1 1 d . . . O21 O 0.2951(12) 0.6669(8) 0.7922(2) 0.123(3) Uani 1 1 d . . . O22 O 0.5703(9) 0.6942(4) 0.85368(19) 0.0672(16) Uani 1 1 d . . . C23 C 0.4038(17) 0.7300(8) 0.8949(3) 0.070(2) Uani 1 1 d . . . C231 C 0.5685(16) 0.7472(8) 0.9425(3) 0.103(3) Uani 1 1 d . . . H23A H 0.6763 0.8091 0.9354 0.155 Uiso 1 1 calc R . . H23B H 0.6576 0.6784 0.9487 0.155 Uiso 1 1 calc R . . H23C H 0.4747 0.7649 0.9730 0.155 Uiso 1 1 calc R . . C232 C 0.2346(17) 0.6348(8) 0.9070(3) 0.092(3) Uani 1 1 d . . . H23D H 0.3226 0.5682 0.9175 0.138 Uiso 1 1 calc R . . H23E H 0.1425 0.6174 0.8761 0.138 Uiso 1 1 calc R . . H23F H 0.1301 0.6577 0.9350 0.138 Uiso 1 1 calc R . . C233 C 0.282(2) 0.8381(8) 0.8796(3) 0.132(4) Uani 1 1 d . . . H23G H 0.3990 0.8964 0.8730 0.198 Uiso 1 1 calc R . . H23H H 0.1787 0.8623 0.9076 0.198 Uiso 1 1 calc R . . H23I H 0.1901 0.8256 0.8482 0.198 Uiso 1 1 calc R . . C3 C 0.6705(18) 0.5441(9) 0.7320(3) 0.095(4) Uani 1 1 d . . . H3A H 0.8089 0.4976 0.7241 0.114 Uiso 1 1 calc R . . H3B H 0.5196 0.5038 0.7304 0.114 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 C11 0.045(5) 0.084(6) 0.053(5) -0.006(5) 0.001(5) 0.013(6) C12 0.054(6) 0.097(7) 0.063(5) -0.003(5) 0.001(5) 0.006(6) C13 0.069(6) 0.081(6) 0.057(5) 0.002(5) -0.011(5) 0.013(7) C14 0.071(6) 0.048(5) 0.051(5) 0.008(4) 0.004(6) -0.007(6) C15 0.057(6) 0.072(6) 0.064(5) 0.009(5) 0.008(6) 0.019(6) C16 0.058(6) 0.085(6) 0.061(6) 0.014(5) -0.009(6) -0.003(7) O14 0.098(5) 0.088(4) 0.053(3) -0.012(3) 0.005(4) 0.013(4) C141 0.106(7) 0.102(7) 0.058(5) -0.011(5) -0.011(6) -0.013(8) C1 0.064(6) 0.119(9) 0.064(5) -0.005(6) 0.011(6) -0.012(7) C10 0.201(13) 0.150(11) 0.091(7) -0.033(7) 0.034(8) -0.090(11) N1 0.060(6) 0.092(6) 0.050(4) 0.004(4) -0.005(4) 0.005(5) C2 0.048(6) 0.142(8) 0.040(5) 0.004(5) 0.005(5) 0.018(7) C21 0.054(6) 0.135(9) 0.056(6) 0.001(6) -0.008(6) 0.000(7) O21 0.056(4) 0.249(9) 0.063(4) -0.016(5) -0.009(4) 0.005(7) O22 0.055(3) 0.101(4) 0.046(3) -0.007(3) -0.003(3) -0.004(4) C23 0.063(6) 0.093(7) 0.053(5) -0.004(5) 0.004(6) -0.017(7) C231 0.092(7) 0.139(9) 0.078(6) -0.033(6) 0.007(6) 0.003(8) C232 0.079(7) 0.120(8) 0.077(6) 0.014(5) 0.018(6) 0.001(8) C233 0.153(11) 0.098(8) 0.145(8) 0.030(7) 0.022(9) 0.057(9) C3 0.107(10) 0.114(8) 0.065(5) 0.000(6) 0.020(6) 0.019(8) _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 C11 C16 1.354(9) . ? C11 C12 1.359(9) . ? C11 C1 1.499(10) . ? C12 C13 1.386(8) . ? C12 H12 0.9300 . ? C13 C14 1.373(10) . ? C13 H13 0.9300 . ? C14 O14 1.367(8) . ? C14 C15 1.376(9) . ? C15 C16 1.405(9) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? O14 C141 1.432(8) . ? C141 H14A 0.9600 . ? C141 H14B 0.9600 . ? C141 H14C 0.9600 . ? C1 N1 1.474(10) . ? C1 C10 1.497(11) . ? C1 H1 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N1 C3 1.433(9) . ? N1 C2 1.484(8) . ? C2 C21 1.452(10) . ? C2 C3 1.481(10) . ? C2 H2 0.9800 . ? C21 O21 1.196(9) . ? C21 O22 1.313(9) . ? O22 C23 1.464(8) . ? C23 C233 1.489(10) . ? C23 C232 1.494(11) . ? C23 C231 1.533(10) . ? C231 H23A 0.9600 . ? C231 H23B 0.9600 . ? C231 H23C 0.9600 . ? C232 H23D 0.9600 . ? C232 H23E 0.9600 . ? C232 H23F 0.9600 . ? C233 H23G 0.9600 . ? C233 H23H 0.9600 . ? C233 H23I 0.9600 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? 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 C16 C11 C12 116.1(7) . . ? C16 C11 C1 121.7(8) . . ? C12 C11 C1 122.2(9) . . ? C11 C12 C13 123.5(8) . . ? C11 C12 H12 118.3 . . ? C13 C12 H12 118.3 . . ? C14 C13 C12 119.2(8) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? O14 C14 C13 126.1(8) . . ? O14 C14 C15 114.6(8) . . ? C13 C14 C15 119.4(7) . . ? C14 C15 C16 118.5(8) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? C11 C16 C15 123.3(8) . . ? C11 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? C14 O14 C141 116.7(7) . . ? O14 C141 H14A 109.5 . . ? O14 C141 H14B 109.5 . . ? H14A C141 H14B 109.5 . . ? O14 C141 H14C 109.5 . . ? H14A C141 H14C 109.5 . . ? H14B C141 H14C 109.5 . . ? N1 C1 C10 109.6(9) . . ? N1 C1 C11 108.3(7) . . ? C10 C1 C11 113.0(8) . . ? N1 C1 H1 108.6 . . ? C10 C1 H1 108.6 . . ? C11 C1 H1 108.6 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 N1 C1 114.4(8) . . ? C3 N1 C2 61.0(5) . . ? C1 N1 C2 113.5(7) . . ? C21 C2 C3 120.8(9) . . ? C21 C2 N1 116.9(7) . . ? C3 C2 N1 57.8(4) . . ? C21 C2 H2 116.2 . . ? C3 C2 H2 116.2 . . ? N1 C2 H2 116.2 . . ? O21 C21 O22 124.2(9) . . ? O21 C21 C2 124.1(8) . . ? O22 C21 C2 111.7(8) . . ? C21 O22 C23 122.1(7) . . ? O22 C23 C233 110.4(7) . . ? O22 C23 C232 109.9(7) . . ? C233 C23 C232 113.2(8) . . ? O22 C23 C231 102.4(7) . . ? C233 C23 C231 111.8(8) . . ? C232 C23 C231 108.7(7) . . ? C23 C231 H23A 109.5 . . ? C23 C231 H23B 109.5 . . ? H23A C231 H23B 109.5 . . ? C23 C231 H23C 109.5 . . ? H23A C231 H23C 109.5 . . ? H23B C231 H23C 109.5 . . ? C23 C232 H23D 109.5 . . ? C23 C232 H23E 109.5 . . ? H23D C232 H23E 109.5 . . ? C23 C232 H23F 109.5 . . ? H23D C232 H23F 109.5 . . ? H23E C232 H23F 109.5 . . ? C23 C233 H23G 109.5 . . ? C23 C233 H23H 109.5 . . ? H23G C233 H23H 109.5 . . ? C23 C233 H23I 109.5 . . ? H23G C233 H23I 109.5 . . ? H23H C233 H23I 109.5 . . ? N1 C3 C2 61.2(5) . . ? N1 C3 H3A 117.6 . . ? C2 C3 H3A 117.6 . . ? N1 C3 H3B 117.6 . . ? C2 C3 H3B 117.6 . . ? H3A C3 H3B 114.8 . . ? 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 C16 C11 C12 C13 -0.7(12) . . . . ? C1 C11 C12 C13 179.1(8) . . . . ? C11 C12 C13 C14 0.3(12) . . . . ? C12 C13 C14 O14 179.1(7) . . . . ? C12 C13 C14 C15 -0.1(11) . . . . ? O14 C14 C15 C16 -179.0(7) . . . . ? C13 C14 C15 C16 0.3(10) . . . . ? C12 C11 C16 C15 0.9(12) . . . . ? C1 C11 C16 C15 -178.9(8) . . . . ? C14 C15 C16 C11 -0.7(11) . . . . ? C13 C14 O14 C141 -2.4(10) . . . . ? C15 C14 O14 C141 176.8(7) . . . . ? C16 C11 C1 N1 -126.8(9) . . . . ? C12 C11 C1 N1 53.4(11) . . . . ? C16 C11 C1 C10 111.6(10) . . . . ? C12 C11 C1 C10 -68.2(13) . . . . ? C10 C1 N1 C3 -153.0(7) . . . . ? C11 C1 N1 C3 83.4(8) . . . . ? C10 C1 N1 C2 -85.6(9) . . . . ? C11 C1 N1 C2 150.8(7) . . . . ? C3 N1 C2 C21 -111.0(11) . . . . ? C1 N1 C2 C21 143.1(9) . . . . ? C1 N1 C2 C3 -105.9(9) . . . . ? C3 C2 C21 O21 -34.8(17) . . . . ? N1 C2 C21 O21 32.0(18) . . . . ? C3 C2 C21 O22 145.2(8) . . . . ? N1 C2 C21 O22 -147.9(8) . . . . ? O21 C21 O22 C23 -0.3(18) . . . . ? C2 C21 O22 C23 179.7(7) . . . . ? C21 O22 C23 C233 -63.4(11) . . . . ? C21 O22 C23 C232 62.1(10) . . . . ? C21 O22 C23 C231 177.5(8) . . . . ? C1 N1 C3 C2 104.4(7) . . . . ? C21 C2 C3 N1 104.3(9) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 19.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.133 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.034