data_chiba-6ab _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N O' _chemical_formula_sum 'C16 H19 N O' _chemical_formula_weight 241.32 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4412(9) _cell_length_b 7.8614(7) _cell_length_c 15.9788(13) _cell_angle_alpha 90.00 _cell_angle_beta 93.057(4) _cell_angle_gamma 90.00 _cell_volume 1309.71(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5461 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 28.53 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9747 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 17587 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 28.70 _reflns_number_total 3377 _reflns_number_gt 2209 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0677P)^2^+0.1675P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3377 _refine_ls_number_parameters 326 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _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 C7 C 0.7140(3) 0.0991(4) 0.92096(18) 0.0307(6) Uani 0.5388(18) 1 d PD A 1 C8 C 0.6319(2) 0.2547(3) 0.93196(15) 0.0370(5) Uani 0.5388(18) 1 d PD A 1 H8A H 0.5466 0.2175 0.9491 0.044 Uiso 0.5388(18) 1 calc PR A 1 H8B H 0.6192 0.3124 0.8771 0.044 Uiso 0.5388(18) 1 calc PR A 1 C9 C 0.6864(3) 0.3835(4) 0.9961(2) 0.0360(7) Uani 0.5388(18) 1 d PD A 1 H9 H 0.6518 0.4986 0.9807 0.043 Uiso 0.5388(18) 1 calc PR A 1 C10 C 0.8339(6) 0.3861(9) 0.9892(4) 0.0350(12) Uani 0.5388(18) 1 d PD A 1 H10A H 0.8557 0.4147 0.9314 0.042 Uiso 0.5388(18) 1 calc PR A 1 H10B H 0.8734 0.4721 1.0278 0.042 Uiso 0.5388(18) 1 calc PR A 1 C11 C 0.8825(2) 0.2105(4) 1.01258(16) 0.0305(5) Uani 0.5388(18) 1 d PD A 1 C12 C 0.8552(2) 0.1667(3) 1.1022(2) 0.0358(5) Uani 0.5388(18) 1 d PD A 1 H12A H 0.9007 0.2479 1.1407 0.043 Uiso 0.5388(18) 1 calc PR A 1 H12B H 0.8880 0.0511 1.1156 0.043 Uiso 0.5388(18) 1 calc PR A 1 C13 C 0.7120(6) 0.1736(10) 1.1155(5) 0.0381(11) Uani 0.5388(18) 1 d PD A 1 H13A H 0.6983 0.1586 1.1759 0.046 Uiso 0.5388(18) 1 calc PR A 1 H13B H 0.6692 0.0778 1.0850 0.046 Uiso 0.5388(18) 1 calc PR A 1 C14 C 0.6490(2) 0.3413(4) 1.08550(18) 0.0392(6) Uani 0.5388(18) 1 d PD A 1 H14 H 0.5541 0.3230 1.0831 0.047 Uiso 0.5388(18) 1 calc PR A 1 C15 C 0.6779(3) 0.4855(4) 1.14663(19) 0.0491(7) Uani 0.5388(18) 1 d PD A 1 H15 H 0.6729 0.4575 1.2042 0.059 Uiso 0.5388(18) 1 calc PR A 1 C16 C 0.7093(6) 0.6462(7) 1.1308(3) 0.0624(14) Uani 0.5388(18) 1 d PD A 1 H16A H 0.7160 0.6831 1.0746 0.075 Uiso 0.5388(18) 1 calc PR A 1 H16B H 0.7249 0.7239 1.1757 0.075 Uiso 0.5388(18) 1 calc PR A 1 C7A C 0.7031(3) 0.0467(4) 0.9486(2) 0.0304(7) Uani 0.4612(18) 1 d PD A 2 C8A C 0.5978(2) 0.1554(4) 0.98205(17) 0.0396(7) Uani 0.4612(18) 1 d PD A 2 H8A1 H 0.5296 0.0798 1.0016 0.048 Uiso 0.4612(18) 1 calc PR A 2 H8A2 H 0.5597 0.2254 0.9356 0.048 Uiso 0.4612(18) 1 calc PR A 2 C9A C 0.6421(3) 0.2729(5) 1.0539(2) 0.0416(8) Uani 0.4612(18) 1 d PD A 2 H9A H 0.5676 0.2962 1.0890 0.050 Uiso 0.4612(18) 1 calc PR A 2 C10A C 0.7460(7) 0.1795(14) 1.1080(6) 0.0421(17) Uani 0.4612(18) 1 d PD A 2 H10C H 0.7753 0.2515 1.1561 0.050 Uiso 0.4612(18) 1 calc PR A 2 H10D H 0.7110 0.0723 1.1300 0.050 Uiso 0.4612(18) 1 calc PR A 2 C11A C 0.8567(2) 0.1417(4) 1.0537(2) 0.0314(6) Uani 0.4612(18) 1 d PD A 2 C12A C 0.9129(3) 0.3066(4) 1.02188(18) 0.0366(6) Uani 0.4612(18) 1 d PD A 2 H12C H 0.9492 0.3736 1.0700 0.044 Uiso 0.4612(18) 1 calc PR A 2 H12D H 0.9833 0.2800 0.9849 0.044 Uiso 0.4612(18) 1 calc PR A 2 C13A C 0.8115(8) 0.4113(12) 0.9738(5) 0.0427(16) Uani 0.4612(18) 1 d PD A 2 H13C H 0.8491 0.5224 0.9593 0.051 Uiso 0.4612(18) 1 calc PR A 2 H13D H 0.7867 0.3520 0.9207 0.051 Uiso 0.4612(18) 1 calc PR A 2 C14A C 0.6920(4) 0.4427(5) 1.0214(3) 0.0492(11) Uani 0.4612(18) 1 d PD A 2 H14A H 0.6251 0.4858 0.9795 0.059 Uiso 0.4612(18) 1 calc PR A 2 C15A C 0.7163(3) 0.5846(5) 1.0851(3) 0.0620(10) Uani 0.4612(18) 1 d PD A 2 H15A H 0.7728 0.6721 1.0690 0.074 Uiso 0.4612(18) 1 calc PR A 2 C16A C 0.6707(8) 0.6022(13) 1.1580(4) 0.086(2) Uani 0.4612(18) 1 d PD A 2 H16C H 0.6136 0.5194 1.1780 0.103 Uiso 0.4612(18) 1 calc PR A 2 H16D H 0.6941 0.6981 1.1916 0.103 Uiso 0.4612(18) 1 calc PR A 2 C6 C 0.6679(9) -0.0356(9) 0.8608(4) 0.0303(13) Uani 0.5388(18) 1 d PD A 1 C1 C 0.5654(7) -0.0001(13) 0.8050(7) 0.045(2) Uani 0.5388(18) 1 d PD A 1 H1 H 0.5216 0.1056 0.8074 0.053 Uiso 0.5388(18) 1 calc PR A 1 C2 C 0.5273(10) -0.1214(11) 0.7452(6) 0.050(3) Uani 0.5388(18) 1 d PD A 1 H2 H 0.4568 -0.0993 0.7066 0.060 Uiso 0.5388(18) 1 calc PR A 1 C3 C 0.5925(12) -0.2744(13) 0.7422(7) 0.063(4) Uani 0.5388(18) 1 d PD A 1 H3 H 0.5727 -0.3514 0.6975 0.076 Uiso 0.5388(18) 1 calc PR A 1 C4 C 0.6860(10) -0.3170(12) 0.8031(6) 0.059(4) Uani 0.5388(18) 1 d PD A 1 H4 H 0.7251 -0.4260 0.8038 0.070 Uiso 0.5388(18) 1 calc PR A 1 C5 C 0.7205(9) -0.1973(12) 0.8625(5) 0.046(3) Uani 0.5388(18) 1 d PD A 1 H5 H 0.7822 -0.2262 0.9061 0.055 Uiso 0.5388(18) 1 calc PR A 1 C6A C 0.6609(12) -0.0610(11) 0.8761(5) 0.0352(19) Uani 0.4612(18) 1 d PD A 2 C1A C 0.5690(10) -0.0137(16) 0.8142(7) 0.050(3) Uani 0.4612(18) 1 d PD A 2 H1A H 0.5296 0.0947 0.8181 0.060 Uiso 0.4612(18) 1 calc PR A 2 C2A C 0.5325(13) -0.1169(15) 0.7474(8) 0.071(5) Uani 0.4612(18) 1 d PD A 2 H2A H 0.4734 -0.0758 0.7048 0.085 Uiso 0.4612(18) 1 calc PR A 2 C3A C 0.5811(14) -0.2797(15) 0.7418(7) 0.050(3) Uani 0.4612(18) 1 d PD A 2 H3A H 0.5482 -0.3583 0.7010 0.060 Uiso 0.4612(18) 1 calc PR A 2 C4A C 0.6803(11) -0.3221(12) 0.7987(6) 0.046(3) Uani 0.4612(18) 1 d PD A 2 H4A H 0.7206 -0.4297 0.7938 0.055 Uiso 0.4612(18) 1 calc PR A 2 C5A C 0.7230(12) -0.2145(14) 0.8623(7) 0.045(3) Uani 0.4612(18) 1 d PD A 2 H5A H 0.7957 -0.2454 0.8973 0.054 Uiso 0.4612(18) 1 calc PR A 2 N1 N 0.8266(4) 0.0771(5) 0.9565(2) 0.0303(6) Uani 0.5388(18) 1 d P A 1 O1 O 1.01607(13) 0.2140(2) 1.00025(11) 0.0395(4) Uani 0.5388(18) 1 d P A 1 H1B H 1.0482 0.1187 1.0126 0.059 Uiso 0.5388(18) 1 calc PR A 1 N1A N 0.8173(4) 0.0362(6) 0.9805(2) 0.0297(8) Uani 0.4612(18) 1 d P A 2 O1A O 0.94809(17) 0.0501(3) 1.10366(11) 0.0414(5) Uani 0.4612(18) 1 d P A 2 H1A1 H 0.9695 -0.0378 1.0780 0.062 Uiso 0.4612(18) 1 calc PR A 2 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 C7 0.0223(11) 0.0372(16) 0.0323(14) 0.0059(11) -0.0012(10) -0.0016(11) C8 0.0230(10) 0.0444(13) 0.0427(12) 0.0031(10) -0.0063(8) 0.0032(9) C9 0.0254(12) 0.0418(18) 0.0404(17) 0.0052(12) -0.0018(12) 0.0072(13) C10 0.0154(19) 0.038(3) 0.051(2) -0.0016(17) -0.0012(18) -0.0011(17) C11 0.0171(10) 0.0343(14) 0.0397(13) 0.0008(12) -0.0030(9) -0.0005(10) C12 0.0294(14) 0.0388(13) 0.0384(15) 0.0029(11) -0.0058(10) 0.0022(9) C13 0.031(3) 0.0460(19) 0.0378(17) -0.0006(15) 0.0021(18) 0.001(2) C14 0.0246(11) 0.0467(16) 0.0462(16) 0.0005(12) 0.0013(11) 0.0037(11) C15 0.0403(14) 0.0560(17) 0.0504(16) -0.0175(14) -0.0046(11) 0.0146(13) C16 0.062(3) 0.077(3) 0.046(3) -0.032(2) -0.0131(19) 0.032(2) C7A 0.0246(13) 0.0328(18) 0.0340(17) 0.0041(12) 0.0032(12) -0.0015(12) C8A 0.0202(12) 0.0527(17) 0.0456(15) -0.0062(13) -0.0009(10) 0.0003(11) C9A 0.0241(14) 0.058(2) 0.0428(18) -0.0131(15) 0.0044(12) 0.0051(14) C10A 0.031(4) 0.060(3) 0.035(2) 0.0031(17) 0.000(2) 0.002(3) C11A 0.0235(13) 0.0447(17) 0.0259(14) 0.0036(14) -0.0007(11) 0.0022(11) C12A 0.0254(14) 0.0373(16) 0.0467(16) -0.0019(13) -0.0007(11) -0.0060(13) C13A 0.032(3) 0.034(2) 0.060(3) -0.004(2) -0.011(2) 0.006(2) C14A 0.0371(18) 0.056(3) 0.053(3) -0.0089(17) -0.0086(17) 0.0149(18) C15A 0.048(2) 0.064(2) 0.072(3) -0.010(2) -0.0106(17) 0.0158(17) C16A 0.085(6) 0.113(6) 0.057(4) -0.026(4) -0.018(3) 0.043(4) C6 0.0187(19) 0.044(2) 0.028(2) 0.000(2) 0.005(2) -0.0100(16) C1 0.025(3) 0.062(4) 0.045(3) 0.003(3) -0.017(2) -0.011(2) C2 0.048(5) 0.069(6) 0.031(4) -0.014(4) -0.011(3) -0.021(4) C3 0.075(7) 0.067(6) 0.049(5) -0.028(4) 0.015(4) -0.026(4) C4 0.047(5) 0.068(7) 0.061(6) -0.001(4) 0.005(4) 0.005(4) C5 0.032(4) 0.073(5) 0.031(3) -0.013(3) -0.008(2) -0.012(3) C6A 0.024(2) 0.048(3) 0.034(3) 0.002(2) 0.012(2) -0.012(2) C1A 0.055(5) 0.049(4) 0.047(4) -0.004(3) 0.017(4) -0.003(3) C2A 0.054(7) 0.103(10) 0.056(7) 0.022(6) -0.001(5) -0.006(7) C3A 0.040(3) 0.078(7) 0.031(4) -0.002(4) -0.006(3) -0.020(3) C4A 0.053(5) 0.051(5) 0.034(4) -0.024(4) 0.008(3) -0.028(4) C5A 0.037(5) 0.037(3) 0.063(6) -0.013(3) 0.016(3) 0.000(3) N1 0.0209(11) 0.0344(18) 0.0353(18) 0.0018(11) -0.0009(12) -0.0025(11) O1 0.0183(7) 0.0380(9) 0.0617(10) 0.0005(8) -0.0026(6) 0.0001(6) N1A 0.0228(13) 0.035(2) 0.032(2) 0.0032(12) 0.0024(13) -0.0023(13) O1A 0.0336(10) 0.0540(12) 0.0357(10) 0.0074(8) -0.0063(7) 0.0082(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 C7 N1 1.290(5) . ? C7 C6 1.492(5) . ? C7 C8 1.510(4) . ? C8 C9 1.528(4) . ? C9 C14 1.537(4) . ? C9 C10 1.551(7) . ? C10 C11 1.511(6) . ? C11 O1 1.419(3) . ? C11 N1 1.479(5) . ? C11 C12 1.515(3) . ? C12 C13 1.523(6) . ? C13 C14 1.538(8) . ? C14 C15 1.517(4) . ? C15 C16 1.333(6) . ? C7A N1A 1.275(6) . ? C7A C6A 1.483(6) . ? C7A C8A 1.512(4) . ? C8A C9A 1.526(4) . ? C9A C14A 1.534(6) . ? C9A C10A 1.537(9) . ? C10A C11A 1.511(7) . ? C11A O1A 1.409(3) . ? C11A N1A 1.474(6) . ? C11A C12A 1.521(4) . ? C12A C13A 1.518(6) . ? C13A C14A 1.515(9) . ? C14A C15A 1.523(6) . ? C15A C16A 1.288(5) . ? C6 C5 1.384(8) . ? C6 C1 1.385(8) . ? C1 C2 1.393(7) . ? C2 C3 1.384(9) . ? C3 C4 1.383(9) . ? C4 C5 1.371(8) . ? C6A C1A 1.391(10) . ? C6A C5A 1.393(10) . ? C1A C2A 1.378(10) . ? C2A C3A 1.381(11) . ? C3A C4A 1.382(9) . ? C4A C5A 1.378(9) . ? 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 N1 C7 C6 116.3(5) . . ? N1 C7 C8 124.6(3) . . ? C6 C7 C8 119.0(4) . . ? C7 C8 C9 114.9(2) . . ? C8 C9 C14 112.1(3) . . ? C8 C9 C10 107.3(4) . . ? C14 C9 C10 111.7(3) . . ? C11 C10 C9 107.0(4) . . ? O1 C11 N1 106.8(2) . . ? O1 C11 C10 105.5(3) . . ? N1 C11 C10 112.4(3) . . ? O1 C11 C12 111.81(18) . . ? N1 C11 C12 108.9(3) . . ? C10 C11 C12 111.3(3) . . ? C11 C12 C13 111.0(4) . . ? C12 C13 C14 113.2(5) . . ? C15 C14 C9 112.7(3) . . ? C15 C14 C13 111.9(4) . . ? C9 C14 C13 110.5(3) . . ? C16 C15 C14 129.0(3) . . ? N1A C7A C6A 120.5(6) . . ? N1A C7A C8A 125.3(3) . . ? C6A C7A C8A 114.0(5) . . ? C7A C8A C9A 114.2(2) . . ? C8A C9A C14A 111.5(3) . . ? C8A C9A C10A 108.1(5) . . ? C14A C9A C10A 111.3(4) . . ? C11A C10A C9A 108.0(5) . . ? O1A C11A N1A 108.3(3) . . ? O1A C11A C10A 106.9(4) . . ? N1A C11A C10A 112.1(4) . . ? O1A C11A C12A 111.3(2) . . ? N1A C11A C12A 108.1(3) . . ? C10A C11A C12A 110.2(5) . . ? C13A C12A C11A 111.1(4) . . ? C14A C13A C12A 113.9(6) . . ? C13A C14A C15A 110.0(5) . . ? C13A C14A C9A 109.4(4) . . ? C15A C14A C9A 117.3(4) . . ? C16A C15A C14A 128.8(6) . . ? C5 C6 C1 119.3(6) . . ? C5 C6 C7 121.7(6) . . ? C1 C6 C7 118.9(7) . . ? C6 C1 C2 119.1(8) . . ? C3 C2 C1 119.7(7) . . ? C4 C3 C2 121.1(7) . . ? C5 C4 C3 118.1(7) . . ? C4 C5 C6 121.8(6) . . ? C1A C6A C5A 115.4(7) . . ? C1A C6A C7A 124.6(8) . . ? C5A C6A C7A 119.8(8) . . ? C2A C1A C6A 123.0(9) . . ? C1A C2A C3A 120.5(9) . . ? C2A C3A C4A 116.5(9) . . ? C5A C4A C3A 122.6(9) . . ? C4A C5A C6A 120.9(9) . . ? C7 N1 C11 119.5(3) . . ? C7A N1A C11A 119.7(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.210 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.032 _publ_contact_author ; Dr Shunsuke Chiba Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 21 Nanyang Link Singapore 637371 Singapore ; _publ_contact_author_phone '+65 6513 8013' _publ_contact_author_fax '+65 6791 1961' _publ_contact_author_email 'shunsuke@ntu.edu.sg' _publ_requested_journal 'Journal of the American Chemical Society' _publ_section_title ; 'Mn(III)-Mediated Reactions of Cyclopropanols with Vinyl Azides: Synthesis of Pyridine and 2-Azabicyclo[3.3.1]non-2-en-1-ol Derivatives' ; loop_ _publ_author_name _publ_author_address 'Yi-Feng Wang' ;Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 21 Nanyang Link Singapore 637371 Singapore ; 'Shunsuke Chiba' ;Division of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 21 Nanyang Link Singapore 637371 Singapore ;