# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jian Zhou' _publ_contact_author_email jzhou@chem.ecnu.edu.cn loop_ _publ_author_name 'Feng Zhou' 'Miao Ding' 'Tai-Ping Du' 'Gang-Guo Zhu' 'Jian Zhou' data_z _database_code_depnum_ccdc_archive 'CCDC 859777' #TrackingRef '- z.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 N O3' _chemical_formula_weight 279.28 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3660(4) _cell_length_b 9.0252(5) _cell_length_c 10.1518(5) _cell_angle_alpha 84.572(2) _cell_angle_beta 88.905(2) _cell_angle_gamma 89.911(2) _cell_volume 671.74(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9637 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_reflns_number 7853 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2353 _reflns_number_gt 1936 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0590P)^2^+0.2463P] 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 2353 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1290 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 O1 O 0.6849(2) 0.3361(2) 0.94545(16) 0.0718(5) Uani 1 1 d . . . O2 O 0.3175(3) 0.14991(19) 0.70562(17) 0.0757(5) Uani 1 1 d . . . O3 O 0.46961(17) 0.42381(16) 0.81518(13) 0.0520(4) Uani 1 1 d . . . N1 N 0.2724(2) 0.3424(2) 0.54545(16) 0.0562(5) Uani 1 1 d . . . C1 C 0.5245(3) 0.3328(2) 0.9205(2) 0.0504(5) Uani 1 1 d . . . C2 C 0.3884(3) 0.2411(2) 0.99875(18) 0.0477(5) Uani 1 1 d . . . C3 C 0.4449(3) 0.1318(2) 1.0934(2) 0.0547(5) Uani 1 1 d . . . H3A H 0.5683 0.1167 1.1071 0.066 Uiso 1 1 calc R . . C4 C 0.3209(3) 0.0455(3) 1.1672(2) 0.0606(6) Uani 1 1 d . . . H4A H 0.3598 -0.0280 1.2308 0.073 Uiso 1 1 calc R . . C5 C 0.1378(3) 0.0678(3) 1.1470(2) 0.0625(6) Uani 1 1 d . . . H5A H 0.0530 0.0093 1.1970 0.075 Uiso 1 1 calc R . . C6 C 0.0802(3) 0.1774(3) 1.0523(2) 0.0567(6) Uani 1 1 d . . . H6A H -0.0434 0.1922 1.0391 0.068 Uiso 1 1 calc R . . C7 C 0.2048(3) 0.2651(2) 0.97712(19) 0.0466(5) Uani 1 1 d . . . C8 C 0.1481(3) 0.3859(2) 0.8740(2) 0.0503(5) Uani 1 1 d . . . H8A H 0.1320 0.4781 0.9148 0.060 Uiso 1 1 calc R . . H8B H 0.0325 0.3598 0.8383 0.060 Uiso 1 1 calc R . . C9 C 0.2874(3) 0.4091(2) 0.76267(19) 0.0461(5) Uani 1 1 d . . . C10 C 0.2946(3) 0.2811(3) 0.6708(2) 0.0515(5) Uani 1 1 d . . . C11 C 0.2493(3) 0.4976(3) 0.5408(2) 0.0545(5) Uani 1 1 d . . . C12 C 0.2566(3) 0.5423(2) 0.6673(2) 0.0501(5) Uani 1 1 d . . . C13 C 0.2384(3) 0.6902(3) 0.6879(3) 0.0660(6) Uani 1 1 d . . . H13A H 0.2436 0.7203 0.7728 0.079 Uiso 1 1 calc R . . C14 C 0.2123(4) 0.7931(3) 0.5807(4) 0.0887(9) Uani 1 1 d . . . H14A H 0.2008 0.8935 0.5927 0.106 Uiso 1 1 calc R . . C15 C 0.2035(4) 0.7469(4) 0.4565(4) 0.0962(11) Uani 1 1 d . . . H15A H 0.1841 0.8176 0.3854 0.115 Uiso 1 1 calc R . . C16 C 0.2222(3) 0.5984(4) 0.4323(3) 0.0791(8) Uani 1 1 d . . . H16A H 0.2168 0.5686 0.3472 0.095 Uiso 1 1 calc R . . C17 C 0.2791(4) 0.2581(3) 0.4306(2) 0.0792(8) Uani 1 1 d . . . H17A H 0.2966 0.1546 0.4587 0.119 Uiso 1 1 calc R . . H17B H 0.3779 0.2933 0.3731 0.119 Uiso 1 1 calc R . . H17C H 0.1670 0.2707 0.3841 0.119 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 O1 0.0421(9) 0.0971(13) 0.0752(11) -0.0007(9) -0.0105(8) -0.0053(8) O2 0.1007(14) 0.0606(10) 0.0675(11) -0.0136(8) -0.0083(9) 0.0120(9) O3 0.0364(8) 0.0692(9) 0.0503(8) -0.0050(7) -0.0011(6) -0.0046(6) N1 0.0472(10) 0.0811(13) 0.0415(9) -0.0116(8) -0.0004(7) -0.0014(9) C1 0.0395(11) 0.0652(13) 0.0481(11) -0.0120(10) -0.0057(9) 0.0012(9) C2 0.0443(11) 0.0593(12) 0.0414(10) -0.0139(9) -0.0029(8) -0.0004(9) C3 0.0509(12) 0.0687(14) 0.0461(11) -0.0127(10) -0.0080(9) 0.0060(10) C4 0.0692(15) 0.0659(14) 0.0459(12) -0.0007(10) -0.0035(10) 0.0058(11) C5 0.0631(15) 0.0709(15) 0.0522(13) -0.0006(11) 0.0083(10) -0.0056(11) C6 0.0420(12) 0.0727(14) 0.0554(13) -0.0069(11) 0.0018(9) 0.0005(10) C7 0.0451(11) 0.0563(12) 0.0398(10) -0.0107(8) -0.0005(8) 0.0008(9) C8 0.0379(11) 0.0604(12) 0.0526(12) -0.0060(9) 0.0008(9) 0.0007(9) C9 0.0399(11) 0.0567(12) 0.0420(10) -0.0060(9) -0.0029(8) -0.0001(8) C10 0.0456(12) 0.0633(13) 0.0465(11) -0.0087(10) -0.0026(9) 0.0017(9) C11 0.0324(10) 0.0776(15) 0.0506(12) 0.0077(10) 0.0043(8) -0.0042(9) C12 0.0375(11) 0.0621(13) 0.0492(11) 0.0018(9) 0.0030(8) -0.0029(9) C13 0.0550(14) 0.0593(14) 0.0820(17) 0.0016(12) 0.0061(12) -0.0026(11) C14 0.0730(18) 0.0692(17) 0.116(3) 0.0271(17) 0.0165(17) -0.0022(13) C15 0.0630(17) 0.105(2) 0.107(3) 0.057(2) 0.0150(16) 0.0023(16) C16 0.0505(14) 0.119(2) 0.0615(15) 0.0244(15) 0.0068(11) -0.0029(14) C17 0.0686(17) 0.119(2) 0.0540(14) -0.0309(14) 0.0017(12) -0.0082(15) _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 O1 C1 1.214(2) . ? O2 C10 1.216(3) . ? O3 C1 1.353(2) . ? O3 C9 1.464(2) . ? N1 C10 1.351(3) . ? N1 C11 1.407(3) . ? N1 C17 1.451(3) . ? C1 C2 1.473(3) . ? C2 C3 1.380(3) . ? C2 C7 1.387(3) . ? C3 C4 1.366(3) . ? C3 H3A 0.9300 . ? C4 C5 1.380(3) . ? C4 H4A 0.9300 . ? C5 C6 1.385(3) . ? C5 H5A 0.9300 . ? C6 C7 1.383(3) . ? C6 H6A 0.9300 . ? C7 C8 1.503(3) . ? C8 C9 1.512(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C12 1.490(3) . ? C9 C10 1.552(3) . ? C11 C16 1.378(3) . ? C11 C12 1.384(3) . ? C12 C13 1.377(3) . ? C13 C14 1.378(4) . ? C13 H13A 0.9300 . ? C14 C15 1.367(5) . ? C14 H14A 0.9300 . ? C15 C16 1.392(5) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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 C1 O3 C9 120.51(15) . . ? C10 N1 C11 111.44(18) . . ? C10 N1 C17 123.7(2) . . ? C11 N1 C17 124.8(2) . . ? O1 C1 O3 116.48(19) . . ? O1 C1 C2 124.55(19) . . ? O3 C1 C2 118.94(17) . . ? C3 C2 C7 120.5(2) . . ? C3 C2 C1 119.53(18) . . ? C7 C2 C1 119.97(18) . . ? C4 C3 C2 120.5(2) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 119.8(2) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C6 C7 C2 118.66(19) . . ? C6 C7 C8 122.28(18) . . ? C2 C7 C8 119.05(18) . . ? C7 C8 C9 111.58(16) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? O3 C9 C12 106.95(16) . . ? O3 C9 C8 110.65(15) . . ? C12 C9 C8 115.02(16) . . ? O3 C9 C10 107.30(15) . . ? C12 C9 C10 102.34(16) . . ? C8 C9 C10 113.91(17) . . ? O2 C10 N1 126.4(2) . . ? O2 C10 C9 126.02(19) . . ? N1 C10 C9 107.55(18) . . ? C16 C11 C12 121.5(2) . . ? C16 C11 N1 128.7(2) . . ? C12 C11 N1 109.77(18) . . ? C13 C12 C11 120.5(2) . . ? C13 C12 C9 130.6(2) . . ? C11 C12 C9 108.90(19) . . ? C12 C13 C14 119.0(3) . . ? C12 C13 H13A 120.5 . . ? C14 C13 H13A 120.5 . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? C14 C15 C16 122.6(3) . . ? C14 C15 H15A 118.7 . . ? C16 C15 H15A 118.7 . . ? C11 C16 C15 116.6(3) . . ? C11 C16 H16A 121.7 . . ? C15 C16 H16A 121.7 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 C9 O3 C1 O1 168.98(17) . . . . ? C9 O3 C1 C2 -12.8(3) . . . . ? O1 C1 C2 C3 -11.7(3) . . . . ? O3 C1 C2 C3 170.19(18) . . . . ? O1 C1 C2 C7 168.2(2) . . . . ? O3 C1 C2 C7 -9.9(3) . . . . ? C7 C2 C3 C4 0.1(3) . . . . ? C1 C2 C3 C4 179.95(19) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? C5 C6 C7 C2 -0.1(3) . . . . ? C5 C6 C7 C8 -179.56(19) . . . . ? C3 C2 C7 C6 0.0(3) . . . . ? C1 C2 C7 C6 -179.87(18) . . . . ? C3 C2 C7 C8 179.50(18) . . . . ? C1 C2 C7 C8 -0.4(3) . . . . ? C6 C7 C8 C9 -150.19(19) . . . . ? C2 C7 C8 C9 30.4(3) . . . . ? C1 O3 C9 C12 168.72(16) . . . . ? C1 O3 C9 C8 42.7(2) . . . . ? C1 O3 C9 C10 -82.1(2) . . . . ? C7 C8 C9 O3 -49.4(2) . . . . ? C7 C8 C9 C12 -170.75(17) . . . . ? C7 C8 C9 C10 71.6(2) . . . . ? C11 N1 C10 O2 -179.9(2) . . . . ? C17 N1 C10 O2 -2.2(3) . . . . ? C11 N1 C10 C9 -0.5(2) . . . . ? C17 N1 C10 C9 177.23(18) . . . . ? O3 C9 C10 O2 67.7(3) . . . . ? C12 C9 C10 O2 -180.0(2) . . . . ? C8 C9 C10 O2 -55.2(3) . . . . ? O3 C9 C10 N1 -111.77(17) . . . . ? C12 C9 C10 N1 0.6(2) . . . . ? C8 C9 C10 N1 125.40(18) . . . . ? C10 N1 C11 C16 -179.6(2) . . . . ? C17 N1 C11 C16 2.7(3) . . . . ? C10 N1 C11 C12 0.1(2) . . . . ? C17 N1 C11 C12 -177.55(19) . . . . ? C16 C11 C12 C13 -0.6(3) . . . . ? N1 C11 C12 C13 179.65(18) . . . . ? C16 C11 C12 C9 -179.91(18) . . . . ? N1 C11 C12 C9 0.3(2) . . . . ? O3 C9 C12 C13 -67.2(3) . . . . ? C8 C9 C12 C13 56.1(3) . . . . ? C10 C9 C12 C13 -179.8(2) . . . . ? O3 C9 C12 C11 112.11(17) . . . . ? C8 C9 C12 C11 -124.58(19) . . . . ? C10 C9 C12 C11 -0.5(2) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C9 C12 C13 C14 179.3(2) . . . . ? C12 C13 C14 C15 0.5(4) . . . . ? C13 C14 C15 C16 -0.9(4) . . . . ? C12 C11 C16 C15 0.2(3) . . . . ? N1 C11 C16 C15 180.0(2) . . . . ? C14 C15 C16 C11 0.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.304 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.037