# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Carreno M. Carmen' 'Maria Ribagorda' 'M. Jesus Sanz-Cuesta' _publ_contact_author_name 'Dr M. Carmen Carreno' _publ_contact_author_address ; Quimica Organica (C-I) Universidad Autonoma de Madrid Cantoblanco Madrid 28049-Madrid SPAIN ; _publ_contact_author_email CARMEN.CARRENNO@UAM.ES _publ_requested_journal 'Chemical Communications' _publ_section_title ; Ring Expansion of Sulfur Substituted p-Quinamines: Regiospecific Synthesis of 4-Aminotropones ; data_troponam _database_code_depnum_ccdc_archive 'CCDC 247411' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 N O3' _chemical_formula_weight 221.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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)/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 8.88460(10) _cell_length_b 12.7624(2) _cell_length_c 10.1950(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.7030(10) _cell_angle_gamma 90.00 _cell_volume 1135.89(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.765 _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 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 4550 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.61 _diffrn_reflns_theta_max 70.23 _reflns_number_total 2015 _reflns_number_gt 1804 _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 i= s not relevant to the choice of reflections for refinement. R-factors base= d 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^)+(0.0492P)^2^+0.3093P] 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 2015 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 C1 C 0.57336(14) -0.25115(10) 0.14876(13) 0.0227(3) Uani 1 1 d . . . C2 C 0.66790(15) -0.24969(10) 0.04760(13) 0.0238(3) Uani 1 1 d . . . C3 C 0.73569(15) -0.16718(10) -0.00255(13) 0.0238(3) Uani 1 1 d . . . C4 C 0.73724(14) -0.05788(10) 0.02426(12) 0.0225(3) Uani 1 1 d . . . C5 C 0.66412(13) -0.00604(9) 0.11193(12) 0.0205(3) Uani 1 1 d . . . C6 C 0.56904(14) -0.05377(10) 0.19492(13) 0.0230(3) Uani 1 1 d . . . C7 C 0.53202(15) -0.15521(10) 0.21034(13) 0.0238(3) Uani 1 1 d . . . C8 C 0.78229(14) 0.16792(9) 0.09227(12) 0.0219(3) Uani 1 1 d . . . C9 C 0.84910(15) 0.35463(9) 0.09650(13) 0.0241(3) Uani 1 1 d . . . C10 C 0.87771(19) 0.35424(12) -0.04614(14) 0.0323(3) Uani 1 1 d . . . C11 C 0.99440(17) 0.34704(12) 0.19981(15) 0.0308(3) Uani 1 1 d . . . C12 C 0.75726(18) 0.45062(11) 0.12039(19) 0.0372(4) Uani 1 1 d . . . N1 N 0.67251(12) 0.10316(8) 0.12687(10) 0.0214(3) Uani 1 1 d . . . O1 O 0.52460(11) -0.33603(7) 0.18486(9) 0.0282(2) Uani 1 1 d . . . O2 O 0.89323(11) 0.14033(7) 0.04881(11) 0.0327(3) Uani 1 1 d . . . O3 O 0.74552(10) 0.26749(7) 0.11709(9) 0.0238(2) Uani 1 1 d . . . H1 H 0.6099(19) 0.1327(12) 0.1725(16) 0.028(4) Uiso 1 1 d . . . H2 H 0.6867(16) -0.3194(12) 0.0131(14) 0.020(3) Uiso 1 1 d . . . H3 H 0.7960(18) -0.1865(12) -0.0691(16) 0.029(4) Uiso 1 1 d . . . H4 H 0.7999(16) -0.0152(12) -0.0246(14) 0.023(3) Uiso 1 1 d . . . H6 H 0.5250(16) -0.0040(12) 0.2500(15) 0.025(4) Uiso 1 1 d . . . H7 H 0.4674(19) -0.1705(13) 0.2740(17) 0.032(4) Uiso 1 1 d . . . H10A H 0.781(2) 0.3448(14) -0.1068(18) 0.043(5) Uiso 1 1 d . . . H10B H 0.954(2) 0.2992(15) -0.0609(17) 0.041(5) Uiso 1 1 d . . . H10C H 0.921(2) 0.4237(14) -0.0623(17) 0.042(5) Uiso 1 1 d . . . H11A H 1.0498(19) 0.2831(14) 0.1916(16) 0.037(4) Uiso 1 1 d . . . H11B H 1.061(2) 0.4052(15) 0.1849(18) 0.043(5) Uiso 1 1 d . . . H11C H 0.973(2) 0.3528(14) 0.293(2) 0.047(5) Uiso 1 1 d . . . H12A H 0.816(2) 0.5146(15) 0.1096(17) 0.041(5) Uiso 1 1 d . . . H12B H 0.656(2) 0.4522(15) 0.0530(19) 0.053(5) Uiso 1 1 d . . . H12C H 0.741(2) 0.4518(15) 0.211(2) 0.051(5) 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 C1 0.0234(6) 0.0209(6) 0.0239(6) 0.0021(5) 0.0050(5) -0.0002(5) C2 0.0275(6) 0.0196(6) 0.0251(7) -0.0019(5) 0.0069(5) 0.0022(5) C3 0.0261(6) 0.0244(7) 0.0228(6) -0.0016(5) 0.0091(5) 0.0027(5) C4 0.0248(6) 0.0210(6) 0.0227(6) 0.0016(5) 0.0074(5) -0.0009(5) C5 0.0214(6) 0.0177(6) 0.0220(6) 0.0013(4) 0.0033(5) 0.0000(5) C6 0.0256(6) 0.0207(6) 0.0244(6) -0.0006(5) 0.0088(5) 0.0018(5) C7 0.0261(6) 0.0219(6) 0.0255(7) 0.0020(5) 0.0108(5) 0.0000(5) C8 0.0253(6) 0.0194(6) 0.0225(6) -0.0005(5) 0.0081(5) -0.0010(5) C9 0.0267(6) 0.0188(6) 0.0291(7) 0.0012(5) 0.0109(6) -0.0048(5) C10 0.0382(8) 0.0322(8) 0.0276(8) 0.0037(6) 0.0093(6) -0.0106(6) C11 0.0314(7) 0.0295(8) 0.0317(8) -0.0008(6) 0.0064(6) -0.0071(6) C12 0.0362(8) 0.0201(7) 0.0605(11) 0.0023(6) 0.0224(8) -0.0024(6) N1 0.0248(5) 0.0173(5) 0.0246(5) -0.0008(4) 0.0109(5) 0.0002(4) O1 0.0354(5) 0.0189(5) 0.0334(5) 0.0019(4) 0.0145(4) -0.0017(4) O2 0.0323(5) 0.0234(5) 0.0479(6) -0.0046(4) 0.0219(5) -0.0031(4) O3 0.0257(5) 0.0177(5) 0.0305(5) 0.0002(3) 0.0122(4) -0.0024(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 (isotropi= c) 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 C1 O1 1.2474(15) . ? C1 C2 1.4461(19) . ? C1 C7 1.4539(18) . ? C2 C3 1.3592(19) . ? C2 H2 0.982(15) . ? C3 C4 1.4210(18) . ? C3 H3 0.971(17) . ? C4 C5 1.3691(18) . ? C4 H4 0.978(15) . ? C5 N1 1.4024(16) . ? C5 C6 1.4374(17) . ? C6 C7 1.3521(18) . ? C6 H6 0.976(15) . ? C7 H7 0.963(18) . ? C8 O2 1.2059(16) . ? C8 O3 1.3477(15) . ? C8 N1 1.3735(16) . ? C9 O3 1.4831(14) . ? C9 C11 1.5100(19) . ? C9 C12 1.5165(19) . ? C9 C10 1.5220(19) . ? C10 H10A 0.968(19) . ? C10 H10B 1.008(19) . ? C10 H10C 0.991(18) . ? C11 H11A 0.965(18) . ? C11 H11B 0.980(19) . ? C11 H11C 1.01(2) . ? C12 H12A 0.989(19) . ? C12 H12B 1.03(2) . ? C12 H12C 0.96(2) . ? N1 H1 0.874(18) . ? 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 O1 C1 C2 120.08(11) . . ? O1 C1 C7 118.32(11) . . ? C2 C1 C7 121.59(11) . . ? C3 C2 C1 129.41(12) . . ? C3 C2 H2 116.8(9) . . ? C1 C2 H2 113.8(9) . . ? C2 C3 C4 132.63(12) . . ? C2 C3 H3 114.0(9) . . ? C4 C3 H3 113.4(9) . . ? C5 C4 C3 127.67(12) . . ? C5 C4 H4 116.6(9) . . ? C3 C4 H4 115.7(9) . . ? C4 C5 N1 121.94(11) . . ? C4 C5 C6 125.55(12) . . ? N1 C5 C6 112.49(11) . . ? C7 C6 C5 131.04(12) . . ? C7 C6 H6 115.1(9) . . ? C5 C6 H6 113.9(9) . . ? C6 C7 C1 132.04(12) . . ? C6 C7 H7 117.5(10) . . ? C1 C7 H7 110.5(10) . . ? O2 C8 O3 125.98(11) . . ? O2 C8 N1 125.91(12) . . ? O3 C8 N1 108.10(10) . . ? O3 C9 C11 109.01(10) . . ? O3 C9 C12 102.50(10) . . ? C11 C9 C12 110.83(12) . . ? O3 C9 C10 110.55(10) . . ? C11 C9 C10 113.16(12) . . ? C12 C9 C10 110.27(12) . . ? C9 C10 H10A 109.0(11) . . ? C9 C10 H10B 112.5(10) . . ? H10A C10 H10B 111.1(15) . . ? C9 C10 H10C 107.1(10) . . ? H10A C10 H10C 109.3(14) . . ? H10B C10 H10C 107.8(15) . . ? C9 C11 H11A 112.2(10) . . ? C9 C11 H11B 107.9(10) . . ? H11A C11 H11B 107.1(15) . . ? C9 C11 H11C 111.3(11) . . ? H11A C11 H11C 109.5(14) . . ? H11B C11 H11C 108.6(14) . . ? C9 C12 H12A 109.6(10) . . ? C9 C12 H12B 109.9(11) . . ? H12A C12 H12B 109.1(14) . . ? C9 C12 H12C 110.3(11) . . ? H12A C12 H12C 105.8(15) . . ? H12B C12 H12C 111.9(16) . . ? C8 N1 C5 126.58(11) . . ? C8 N1 H1 115.5(10) . . ? C5 N1 H1 117.4(10) . . ? C8 O3 C9 120.13(9) . . ? 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 O1 C1 C2 C3 -177.84(13) . . . . ? C7 C1 C2 C3 2.5(2) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? C2 C3 C4 C5 -0.9(2) . . . . ? C3 C4 C5 N1 -178.59(12) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C4 C5 C6 C7 1.8(2) . . . . ? N1 C5 C6 C7 -179.77(13) . . . . ? C5 C6 C7 C1 -0.6(2) . . . . ? O1 C1 C7 C6 178.28(13) . . . . ? C2 C1 C7 C6 -2.0(2) . . . . ? O2 C8 N1 C5 -3.6(2) . . . . ? O3 C8 N1 C5 177.28(11) . . . . ? C4 C5 N1 C8 -20.59(18) . . . . ? C6 C5 N1 C8 160.94(11) . . . . ? O2 C8 O3 C9 -2.70(19) . . . . ? N1 C8 O3 C9 176.46(10) . . . . ? C11 C9 O3 C8 -68.57(14) . . . . ? C12 C9 O3 C8 173.94(11) . . . . ? C10 C9 O3 C8 56.42(15) . . . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 70.23 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 0.210 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.039