data_shelxl _audit_creation_method SHELXL-97 _publ_section_references ; CrystalClear, Rigaku Corp., (1999) Altomare, A., M. Burla, M. Camalli, G. Cascarano, C. Giacovazzo A. Guagliardi, A. Moliterni, G. Polidori & R. Spagna. (1999) J. Appl. Cryst. 32, 115-119. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 N O3' _chemical_formula_weight 269.29 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 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0234(10) _cell_length_b 9.1282(15) _cell_length_c 10.3014(13) _cell_angle_alpha 78.99(2) _cell_angle_beta 70.106(18) _cell_angle_gamma 65.402(15) _cell_volume 724.25(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(1) _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7722 _diffrn_ambient_temperature 296(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method 'phi and omega rotations' _diffrn_reflns_number 6510 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2515 _reflns_number_gt 2016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 1999)' _computing_data_reduction 'CrystalClear (Rigaku, 1999)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0938P)^2^+0.0459P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2515 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1367 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.58570(18) 0.57153(18) 0.25679(14) 0.0509(4) Uani 1 1 d . . . C2 C 0.52463(18) 0.36002(17) 0.22116(15) 0.0534(4) Uani 1 1 d . . . C3 C 0.5285(2) 0.30898(18) 0.10154(15) 0.0588(4) Uani 1 1 d . . . H3 H 0.6067 0.3216 0.0183 0.078 Uiso 1 1 calc R . . C4 C 0.4176(2) 0.23946(18) 0.10410(15) 0.0596(4) Uani 1 1 d . . . H4 H 0.4191 0.2090 0.0224 0.079 Uiso 1 1 calc R . . C5 C 0.30423(19) 0.21504(18) 0.22807(15) 0.0557(4) Uani 1 1 d . . . C6 C 0.3056(2) 0.2588(2) 0.34913(15) 0.0632(4) Uani 1 1 d . . . H6 H 0.2332 0.2389 0.4333 0.084 Uiso 1 1 calc R . . C7 C 0.4135(2) 0.3314(2) 0.34565(15) 0.0614(4) Uani 1 1 d . . . H7 H 0.4120 0.3618 0.4274 0.082 Uiso 1 1 calc R . . C8 C 0.1716(3) 0.1161(2) 0.1191(2) 0.0802(5) Uani 1 1 d . . . H8A H 0.1524 0.2120 0.0589 0.120 Uiso 1 1 calc R . . H8B H 0.0768 0.0837 0.1422 0.120 Uiso 1 1 calc R . . H8C H 0.2738 0.0313 0.0732 0.120 Uiso 1 1 calc R . . C9 C 0.70320(18) 0.64948(18) 0.24860(15) 0.0544(4) Uani 1 1 d . . . C10 C 0.8777(2) 0.5634(2) 0.2128(2) 0.0773(5) Uani 1 1 d . . . H10 H 0.9215 0.4549 0.1953 0.103 Uiso 1 1 calc R . . C11 C 0.9872(2) 0.6375(3) 0.2030(3) 0.0949(7) Uani 1 1 d . . . H11 H 1.1040 0.5781 0.1804 0.126 Uiso 1 1 calc R . . C12 C 0.9249(3) 0.7970(2) 0.2262(2) 0.0867(6) Uani 1 1 d . . . H12 H 0.9994 0.8464 0.2186 0.115 Uiso 1 1 calc R . . C13 C 0.7536(2) 0.8847(2) 0.2606(2) 0.0763(5) Uani 1 1 d . . . H13 H 0.7115 0.9937 0.2760 0.102 Uiso 1 1 calc R . . C14 C 0.6426(2) 0.8112(2) 0.27250(17) 0.0629(4) Uani 1 1 d . . . H14 H 0.5259 0.8712 0.2969 0.084 Uiso 1 1 calc R . . C15 C 0.39681(18) 0.67149(18) 0.31253(14) 0.0524(4) Uani 1 1 d . . . C16 C 0.1744(2) 0.7790(3) 0.5122(2) 0.0967(7) Uani 1 1 d . . . H16A H 0.1474 0.8855 0.4679 0.145 Uiso 1 1 calc R . . H16B H 0.1567 0.7853 0.6086 0.145 Uiso 1 1 calc R . . H16C H 0.1022 0.7315 0.5022 0.145 Uiso 1 1 calc R . . N1 N 0.64031(15) 0.43237(16) 0.21172(13) 0.0578(4) Uani 1 1 d . . . O1 O 0.18931(16) 0.14739(15) 0.24191(12) 0.0736(4) Uani 1 1 d . . . O2 O 0.30480(13) 0.73562(14) 0.24103(12) 0.0704(4) Uani 1 1 d . . . O3 O 0.35069(12) 0.68070(14) 0.44866(10) 0.0676(4) Uani 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 0.0436(8) 0.0508(9) 0.0523(8) 0.0013(6) -0.0151(6) -0.0131(6) C2 0.0487(8) 0.0444(8) 0.0594(8) -0.0019(6) -0.0128(6) -0.0131(7) C3 0.0613(9) 0.0528(9) 0.0528(8) -0.0043(6) -0.0058(6) -0.0207(7) C4 0.0688(10) 0.0505(9) 0.0542(8) -0.0053(6) -0.0132(7) -0.0205(8) C5 0.0577(9) 0.0446(8) 0.0607(9) -0.0019(6) -0.0136(7) -0.0189(7) C6 0.0674(10) 0.0673(10) 0.0515(8) 0.0004(7) -0.0085(7) -0.0313(8) C7 0.0658(10) 0.0659(10) 0.0523(8) -0.0032(7) -0.0136(7) -0.0278(8) C8 0.0933(14) 0.0768(12) 0.0848(12) -0.0112(9) -0.0255(10) -0.0434(11) C9 0.0452(8) 0.0520(9) 0.0623(8) 0.0051(6) -0.0198(6) -0.0154(7) C10 0.0472(9) 0.0540(10) 0.1213(15) 0.0048(9) -0.0241(9) -0.0149(8) C11 0.0508(10) 0.0753(14) 0.156(2) 0.0184(12) -0.0409(11) -0.0243(10) C12 0.0745(13) 0.0716(13) 0.1329(17) 0.0249(11) -0.0536(12) -0.0403(11) C13 0.0795(12) 0.0589(10) 0.1030(13) 0.0069(9) -0.0430(10) -0.0301(9) C14 0.0548(9) 0.0551(10) 0.0784(10) 0.0008(7) -0.0271(7) -0.0166(7) C15 0.0450(8) 0.0529(9) 0.0582(8) -0.0027(6) -0.0176(6) -0.0159(7) C16 0.0542(10) 0.1120(17) 0.0846(13) -0.0223(11) -0.0021(9) -0.0016(11) N1 0.0501(7) 0.0533(8) 0.0635(7) -0.0040(6) -0.0115(6) -0.0171(6) O1 0.0847(9) 0.0762(8) 0.0705(7) -0.0066(6) -0.0134(6) -0.0471(7) O2 0.0530(7) 0.0768(8) 0.0756(7) -0.0038(6) -0.0307(5) -0.0101(6) O3 0.0460(6) 0.0800(8) 0.0604(7) -0.0094(5) -0.0126(5) -0.0084(6) 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 N1 1.273(2) . ? C1 C9 1.477(2) . ? C1 C15 1.519(2) . ? C2 C3 1.383(2) . ? C2 C7 1.390(2) . ? C2 N1 1.4198(19) . ? C3 C4 1.381(2) . ? C4 C5 1.385(2) . ? C5 O1 1.3696(18) . ? C5 C6 1.385(2) . ? C6 C7 1.376(2) . ? C8 O1 1.422(2) . ? C9 C14 1.383(2) . ? C9 C10 1.385(2) . ? C10 C11 1.380(3) . ? C11 C12 1.362(3) . ? C12 C13 1.364(3) . ? C13 C14 1.382(2) . ? C15 O2 1.1922(17) . ? C15 O3 1.3288(17) . ? C16 O3 1.446(2) . ? 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 C1 C9 121.45(13) . . ? N1 C1 C15 122.25(13) . . ? C9 C1 C15 116.16(13) . . ? C3 C2 C7 118.56(14) . . ? C3 C2 N1 118.28(13) . . ? C7 C2 N1 123.10(13) . . ? C4 C3 C2 120.86(14) . . ? C3 C4 C5 120.17(14) . . ? O1 C5 C4 124.79(13) . . ? O1 C5 C6 116.03(13) . . ? C4 C5 C6 119.17(14) . . ? C7 C6 C5 120.42(14) . . ? C6 C7 C2 120.70(14) . . ? C14 C9 C10 118.18(15) . . ? C14 C9 C1 121.04(14) . . ? C10 C9 C1 120.75(14) . . ? C11 C10 C9 120.56(17) . . ? C12 C11 C10 120.29(18) . . ? C11 C12 C13 120.27(17) . . ? C12 C13 C14 119.92(17) . . ? C13 C14 C9 120.78(16) . . ? O2 C15 O3 125.31(14) . . ? O2 C15 C1 123.39(13) . . ? O3 C15 C1 111.28(11) . . ? C1 N1 C2 120.31(13) . . ? C5 O1 C8 117.73(13) . . ? C15 O3 C16 116.03(13) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.202 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.038