# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email 597484267@qq.com loop_ _publ_author_name 'Ziming Xia' 'Kuo Wang' 'Jiening Zheng' 'Zheyong Ma' 'Zhanguo Jiang' 'Xiaoxia Wang' 'Xin Lv' data_a _database_code_depnum_ccdc_archive 'CCDC 832179' #TrackingRef 'A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H9 N O2' _chemical_formula_weight 235.23 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)/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 12.2370(13) _cell_length_b 7.6556(8) _cell_length_c 12.2370(13) _cell_angle_alpha 90.00 _cell_angle_beta 108.92 _cell_angle_gamma 90.00 _cell_volume 1084.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.348 _exptl_crystal_size_mid 0.259 _exptl_crystal_size_min 0.101 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.990 _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9119 _diffrn_reflns_av_R_equivalents 0.1583 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.57 _reflns_number_total 2452 _reflns_number_gt 1074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1000P)^2^+3.4650P] 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 SHELXL _refine_ls_extinction_coef 0.025(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2452 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1756 _refine_ls_R_factor_gt 0.0983 _refine_ls_wR_factor_ref 0.3158 _refine_ls_wR_factor_gt 0.2342 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _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 O2 O 0.0811(3) 0.2356(4) 0.5210(3) 0.0648(10) Uani 1 1 d . . . O1 O -0.0215(3) 0.5385(5) 0.2297(3) 0.0683(10) Uani 1 1 d . . . N1 N -0.0637(3) 0.3735(5) 0.3655(3) 0.0573(10) Uani 1 1 d . . . C9 C 0.0122(4) 0.4490(6) 0.3148(3) 0.0548(11) Uani 1 1 d . . . C11 C 0.1624(4) 0.3031(6) 0.4750(4) 0.0577(11) Uani 1 1 d . . . C8 C -0.0313(4) 0.2644(6) 0.4613(4) 0.0543(11) Uani 1 1 d . . . C10 C 0.1312(4) 0.4026(6) 0.3779(4) 0.0574(11) Uani 1 1 d . . . C5 C -0.1856(4) 0.3772(6) 0.3243(4) 0.0584(11) Uani 1 1 d . . . C7 C -0.1222(4) 0.2004(7) 0.4862(4) 0.0648(12) Uani 1 1 d . . . H7A H -0.1212 0.1277 0.5474 0.078 Uiso 1 1 calc R . . C15 C 0.2189(4) 0.4666(7) 0.3368(5) 0.0690(13) Uani 1 1 d . . . H15A H 0.2005 0.5343 0.2702 0.083 Uiso 1 1 calc R . . C6 C -0.2585(4) 0.4619(7) 0.2297(4) 0.0664(13) Uani 1 1 d . . . H6A H -0.2311 0.5337 0.1830 0.080 Uiso 1 1 calc R . . C12 C 0.2759(5) 0.2608(7) 0.5360(5) 0.0721(14) Uani 1 1 d . . . H12A H 0.2946 0.1918 0.6021 0.086 Uiso 1 1 calc R . . C14 C 0.3317(5) 0.4271(8) 0.3970(5) 0.0796(16) Uani 1 1 d . . . H14A H 0.3902 0.4700 0.3713 0.096 Uiso 1 1 calc R . . C13 C 0.3598(5) 0.3253(8) 0.4945(5) 0.0799(16) Uani 1 1 d . . . H13A H 0.4369 0.2995 0.5332 0.096 Uiso 1 1 calc R . . C4 C -0.2214(4) 0.2679(7) 0.3982(4) 0.0652(13) Uani 1 1 d . . . C2 C -0.4146(5) 0.3261(9) 0.2806(5) 0.0858(18) Uani 1 1 d . . . H2A H -0.4935 0.3089 0.2641 0.103 Uiso 1 1 calc R . . C3 C -0.3399(5) 0.2453(8) 0.3750(5) 0.0783(16) Uani 1 1 d . . . H3A H -0.3675 0.1765 0.4229 0.094 Uiso 1 1 calc R . . C1 C -0.3763(5) 0.4333(9) 0.2083(5) 0.0837(18) Uani 1 1 d . . . H1A H -0.4299 0.4864 0.1450 0.100 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 O2 0.065(2) 0.069(2) 0.0527(17) 0.0114(15) 0.0087(15) 0.0043(16) O1 0.072(2) 0.070(2) 0.0580(19) 0.0134(17) 0.0131(15) 0.0020(17) N1 0.058(2) 0.061(2) 0.0450(18) 0.0007(17) 0.0054(15) 0.0011(17) C9 0.065(3) 0.053(2) 0.041(2) 0.0020(18) 0.0082(18) 0.000(2) C11 0.059(2) 0.059(2) 0.049(2) -0.004(2) 0.0080(18) 0.000(2) C8 0.057(2) 0.055(2) 0.046(2) 0.0008(19) 0.0088(18) 0.0039(19) C10 0.061(3) 0.055(2) 0.049(2) -0.004(2) 0.0079(19) -0.002(2) C5 0.058(2) 0.063(3) 0.046(2) -0.005(2) 0.0048(18) 0.006(2) C7 0.075(3) 0.063(3) 0.055(3) 0.006(2) 0.020(2) -0.003(2) C15 0.071(3) 0.067(3) 0.065(3) 0.000(2) 0.017(2) -0.006(2) C6 0.064(3) 0.069(3) 0.058(3) 0.001(2) 0.008(2) 0.005(2) C12 0.069(3) 0.071(3) 0.060(3) -0.002(2) -0.001(2) 0.006(3) C14 0.062(3) 0.090(4) 0.085(4) -0.009(3) 0.021(3) -0.009(3) C13 0.063(3) 0.085(4) 0.079(4) -0.014(3) 0.005(3) -0.003(3) C4 0.070(3) 0.065(3) 0.055(3) -0.012(2) 0.013(2) 0.000(2) C2 0.068(3) 0.104(5) 0.081(4) -0.019(4) 0.018(3) -0.003(3) C3 0.068(3) 0.087(4) 0.077(3) -0.013(3) 0.021(3) -0.009(3) C1 0.063(3) 0.097(4) 0.074(3) -0.011(3) -0.001(3) 0.016(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 (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 O2 C8 1.350(5) . ? O2 C11 1.392(6) . ? O1 C9 1.202(5) . ? N1 C8 1.388(6) . ? N1 C9 1.398(6) . ? N1 C5 1.411(6) . ? C9 C10 1.454(6) . ? C11 C10 1.357(6) . ? C11 C12 1.386(6) . ? C8 C7 1.338(6) . ? C10 C15 1.412(7) . ? C5 C6 1.373(6) . ? C5 C4 1.403(7) . ? C7 C4 1.432(7) . ? C15 C14 1.371(7) . ? C6 C1 1.397(7) . ? C12 C13 1.376(8) . ? C14 C13 1.372(8) . ? C4 C3 1.395(7) . ? C2 C3 1.367(9) . ? C2 C1 1.395(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 C8 O2 C11 117.2(4) . . ? C8 N1 C9 125.0(4) . . ? C8 N1 C5 107.0(4) . . ? C9 N1 C5 127.6(4) . . ? O1 C9 N1 121.9(4) . . ? O1 C9 C10 127.1(4) . . ? N1 C9 C10 111.0(4) . . ? C10 C11 C12 123.4(5) . . ? C10 C11 O2 121.8(4) . . ? C12 C11 O2 114.7(4) . . ? C7 C8 O2 126.4(4) . . ? C7 C8 N1 112.4(4) . . ? O2 C8 N1 121.2(4) . . ? C11 C10 C15 118.4(4) . . ? C11 C10 C9 123.4(4) . . ? C15 C10 C9 118.1(4) . . ? C6 C5 C4 124.9(5) . . ? C6 C5 N1 129.3(5) . . ? C4 C5 N1 105.8(4) . . ? C8 C7 C4 105.1(4) . . ? C14 C15 C10 118.7(5) . . ? C5 C6 C1 115.7(5) . . ? C13 C12 C11 117.0(5) . . ? C15 C14 C13 121.1(5) . . ? C14 C13 C12 121.2(5) . . ? C3 C4 C5 117.6(5) . . ? C3 C4 C7 132.8(5) . . ? C5 C4 C7 109.5(4) . . ? C3 C2 C1 122.2(6) . . ? C2 C3 C4 118.9(6) . . ? C2 C1 C6 120.8(5) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.461 _refine_diff_density_min -0.570 _refine_diff_density_rms 0.105