data_publication_text _publ_requested_journal J.Org.Chem. _publ_contact_author_name 'Steven L. Castle' _publ_contact_author_address ;Department of Chemistry and Biochemistry Brigham Young University Provo, Utah 84602 ; _publ_contact_author_email scastle@chem.byu.edu _publ_contact_author_phone 801-422-1780 _publ_contact_author_fax 801-422-0153 loop_ _publ_author_name _publ_author_address 'He, Liwen' ;Department of Chemistry and Biochemistry Brigham Young University Provo, Utah 84602 ; 'Srikanth, G. S. C.' ;Department of Chemistry and Biochemistry Brigham Young University Provo, Utah 84602 ; 'Castle, Steven L.' ;Department of Chemistry and Biochemistry Brigham Young University Provo, Utah 84602 ; data_slc1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 N O4' _chemical_formula_weight 207.18 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 10.0106(14) _cell_length_b 10.4397(16) _cell_length_c 11.6615(15) _cell_angle_alpha 68.051(11) _cell_angle_beta 67.541(10) _cell_angle_gamma 70.203(11) _cell_volume 1017.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 46 _cell_measurement_theta_min 5.21 _cell_measurement_theta_max 12.44 _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.106 _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 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 '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4196 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3528 _reflns_number_gt 2678 _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^)+(0.0884P)^2^+0.1477P] 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 3528 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 C1 C 0.7733(2) -0.0228(2) 0.28058(19) 0.0515(5) Uani 1 1 d . . . C2 C 0.6754(2) 0.0802(2) 0.32959(19) 0.0531(5) Uani 1 1 d . . . H2 H 0.6216 0.1478 0.2748 0.064 Uiso 1 1 calc R . . C3 C 0.6373(2) 0.1062(2) 0.45383(19) 0.0515(5) Uani 1 1 d . . . C4 C 0.5650(3) 0.2428(2) 0.4632(2) 0.0676(6) Uani 1 1 d . . . H4 H 0.5436 0.3132 0.3909 0.081 Uiso 1 1 calc R . . C5 C 0.5246(3) 0.2760(3) 0.5764(3) 0.0806(7) Uani 1 1 d . . . H5 H 0.4773 0.3686 0.5801 0.097 Uiso 1 1 calc R . . C6 C 0.5535(3) 0.1736(3) 0.6847(2) 0.0775(7) Uani 1 1 d . . . H6 H 0.5266 0.1964 0.7616 0.093 Uiso 1 1 calc R . . C7 C 0.6225(3) 0.0373(3) 0.6784(2) 0.0786(7) Uani 1 1 d . . . H7 H 0.6416 -0.0326 0.7518 0.094 Uiso 1 1 calc R . . C8 C 0.6634(3) 0.0030(2) 0.5656(2) 0.0675(6) Uani 1 1 d . . . H8 H 0.7093 -0.0901 0.5633 0.081 Uiso 1 1 calc R . . C9 C 0.8047(2) -0.0382(2) 0.1517(2) 0.0566(5) Uani 1 1 d . . . C10 C 0.7444(3) 0.0671(3) -0.0450(2) 0.0806(7) Uani 1 1 d . . . H10A H 0.8455 0.0698 -0.0953 0.121 Uiso 1 1 calc R . . H10B H 0.6790 0.1485 -0.0842 0.121 Uiso 1 1 calc R . . H10C H 0.7236 -0.0177 -0.0416 0.121 Uiso 1 1 calc R . . C11 C 0.2691(2) 0.46393(19) 1.05367(18) 0.0503(5) Uani 1 1 d . . . C12 C 0.1718(2) 0.56723(19) 0.99844(18) 0.0505(5) Uani 1 1 d . . . H12 H 0.1172 0.6348 1.0431 0.061 Uiso 1 1 calc R . . C13 C 0.1354(2) 0.59362(19) 0.88060(18) 0.0492(5) Uani 1 1 d . . . C14 C 0.0523(2) 0.7277(2) 0.8339(2) 0.0564(5) Uani 1 1 d . . . H14 H 0.0227 0.7951 0.8783 0.068 Uiso 1 1 calc R . . C15 C 0.0135(3) 0.7621(2) 0.7232(2) 0.0680(6) Uani 1 1 d . . . H15 H -0.0406 0.8528 0.6926 0.082 Uiso 1 1 calc R . . C16 C 0.0541(3) 0.6636(3) 0.6582(2) 0.0707(6) Uani 1 1 d . . . H16 H 0.0289 0.6876 0.5826 0.085 Uiso 1 1 calc R . . C17 C 0.1320(3) 0.5291(3) 0.7043(2) 0.0738(7) Uani 1 1 d . . . H17 H 0.1572 0.4616 0.6609 0.089 Uiso 1 1 calc R . . C18 C 0.1732(3) 0.4934(2) 0.8141(2) 0.0649(6) Uani 1 1 d . . . H18 H 0.2264 0.4021 0.8443 0.078 Uiso 1 1 calc R . . C19 C 0.2933(2) 0.4455(2) 1.1762(2) 0.0547(5) Uani 1 1 d . . . C20 C 0.2271(3) 0.5472(3) 1.3446(2) 0.0749(7) Uani 1 1 d . . . H20A H 0.1941 0.4668 1.4111 0.112 Uiso 1 1 calc R . . H20B H 0.1677 0.6325 1.3683 0.112 Uiso 1 1 calc R . . H20C H 0.3292 0.5387 1.3344 0.112 Uiso 1 1 calc R . . N1 N 0.8723(2) -0.13690(18) 0.35164(17) 0.0600(5) Uani 1 1 d . . . N11 N 0.3697(2) 0.35179(19) 0.99263(18) 0.0592(5) Uani 1 1 d . . . O1 O 0.9840(2) -0.11110(19) 0.34668(19) 0.0874(6) Uani 1 1 d . . . O2 O 0.8378(2) -0.24944(17) 0.41009(19) 0.0921(6) Uani 1 1 d . . . O3 O 0.89559(19) -0.13352(17) 0.11331(16) 0.0816(5) Uani 1 1 d . . . O4 O 0.72216(17) 0.06827(16) 0.08444(14) 0.0693(4) Uani 1 1 d . . . O11 O 0.3391(2) 0.23771(17) 1.03160(18) 0.0855(5) Uani 1 1 d . . . O12 O 0.4789(2) 0.3803(2) 0.9055(2) 0.0995(7) Uani 1 1 d . . . O13 O 0.3768(2) 0.34395(17) 1.22439(16) 0.0790(5) Uani 1 1 d . . . O14 O 0.21251(16) 0.55269(15) 1.22500(13) 0.0594(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 0.0544(11) 0.0444(10) 0.0546(11) -0.0106(8) -0.0234(9) -0.0053(9) C2 0.0526(11) 0.0509(11) 0.0553(11) -0.0144(9) -0.0222(9) -0.0044(9) C3 0.0468(10) 0.0545(11) 0.0555(11) -0.0204(9) -0.0191(9) -0.0042(9) C4 0.0721(14) 0.0622(13) 0.0660(13) -0.0282(11) -0.0281(11) 0.0081(11) C5 0.0907(18) 0.0715(15) 0.0853(17) -0.0421(14) -0.0331(14) 0.0055(13) C6 0.0785(16) 0.101(2) 0.0658(15) -0.0443(14) -0.0238(12) -0.0098(14) C7 0.0867(17) 0.0900(18) 0.0549(13) -0.0222(12) -0.0282(12) -0.0043(14) C8 0.0779(15) 0.0612(13) 0.0573(12) -0.0190(10) -0.0238(11) -0.0014(11) C9 0.0595(12) 0.0501(11) 0.0597(12) -0.0184(9) -0.0232(10) -0.0019(10) C10 0.0916(18) 0.0878(17) 0.0631(14) -0.0308(13) -0.0401(13) 0.0094(14) C11 0.0495(10) 0.0460(10) 0.0540(11) -0.0158(8) -0.0158(9) -0.0067(8) C12 0.0553(11) 0.0446(10) 0.0513(11) -0.0161(8) -0.0182(9) -0.0050(9) C13 0.0501(10) 0.0475(10) 0.0493(11) -0.0151(8) -0.0153(8) -0.0078(8) C14 0.0606(12) 0.0503(11) 0.0608(12) -0.0161(9) -0.0246(10) -0.0072(9) C15 0.0743(14) 0.0623(13) 0.0655(14) -0.0085(11) -0.0345(11) -0.0078(11) C16 0.0761(15) 0.0886(17) 0.0543(12) -0.0195(12) -0.0289(11) -0.0166(13) C17 0.0833(16) 0.0830(16) 0.0681(14) -0.0398(13) -0.0292(12) -0.0056(13) C18 0.0758(14) 0.0576(12) 0.0681(13) -0.0285(10) -0.0321(11) 0.0015(11) C19 0.0558(11) 0.0481(11) 0.0583(12) -0.0109(9) -0.0234(9) -0.0064(9) C20 0.0972(18) 0.0751(15) 0.0568(13) -0.0237(11) -0.0347(12) -0.0053(13) N1 0.0708(12) 0.0475(10) 0.0568(10) -0.0163(8) -0.0249(9) 0.0015(9) N11 0.0580(11) 0.0553(11) 0.0658(11) -0.0224(8) -0.0241(9) -0.0019(8) O1 0.0726(11) 0.0829(12) 0.1101(14) -0.0197(10) -0.0501(10) -0.0031(9) O2 0.1205(16) 0.0487(10) 0.0963(13) -0.0014(9) -0.0428(11) -0.0148(10) O3 0.0946(12) 0.0698(10) 0.0768(11) -0.0397(9) -0.0384(9) 0.0222(9) O4 0.0733(10) 0.0715(10) 0.0577(9) -0.0256(7) -0.0312(7) 0.0121(8) O11 0.1050(14) 0.0503(10) 0.0989(13) -0.0258(9) -0.0293(10) -0.0104(9) O12 0.0669(11) 0.1047(14) 0.1158(15) -0.0584(12) 0.0107(11) -0.0185(10) O13 0.0990(12) 0.0596(9) 0.0821(11) -0.0203(8) -0.0554(10) 0.0107(9) O14 0.0649(9) 0.0608(8) 0.0535(8) -0.0225(6) -0.0254(7) 0.0009(7) _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 C1 C2 1.326(3) . ? C1 C9 1.473(3) . ? C1 N1 1.476(3) . ? C2 C3 1.456(3) . ? C3 C4 1.388(3) . ? C3 C8 1.396(3) . ? C4 C5 1.366(3) . ? C5 C6 1.371(4) . ? C6 C7 1.371(4) . ? C7 C8 1.366(3) . ? C9 O3 1.195(2) . ? C9 O4 1.325(2) . ? C10 O4 1.443(3) . ? C11 C12 1.332(3) . ? C11 C19 1.472(3) . ? C11 N11 1.472(3) . ? C12 C13 1.459(3) . ? C13 C14 1.391(3) . ? C13 C18 1.397(3) . ? C14 C15 1.374(3) . ? C15 C16 1.365(3) . ? C16 C17 1.372(3) . ? C17 C18 1.375(3) . ? C19 O13 1.205(2) . ? C19 O14 1.319(2) . ? C20 O14 1.435(3) . ? N1 O2 1.208(2) . ? N1 O1 1.212(2) . ? N11 O11 1.206(2) . ? N11 O12 1.209(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 C2 C1 C9 127.13(18) . . ? C2 C1 N1 121.99(18) . . ? C9 C1 N1 110.83(16) . . ? C1 C2 C3 131.49(19) . . ? C4 C3 C8 117.35(19) . . ? C4 C3 C2 117.67(18) . . ? C8 C3 C2 124.95(19) . . ? C5 C4 C3 121.4(2) . . ? C4 C5 C6 120.3(2) . . ? C7 C6 C5 119.4(2) . . ? C8 C7 C6 120.7(2) . . ? C7 C8 C3 120.8(2) . . ? O3 C9 O4 125.1(2) . . ? O3 C9 C1 123.60(19) . . ? O4 C9 C1 111.23(17) . . ? C12 C11 C19 127.02(18) . . ? C12 C11 N11 121.29(18) . . ? C19 C11 N11 111.69(16) . . ? C11 C12 C13 131.74(18) . . ? C14 C13 C18 117.86(18) . . ? C14 C13 C12 117.07(17) . . ? C18 C13 C12 125.03(18) . . ? C15 C14 C13 121.0(2) . . ? C16 C15 C14 120.2(2) . . ? C15 C16 C17 120.0(2) . . ? C16 C17 C18 120.5(2) . . ? C17 C18 C13 120.3(2) . . ? O13 C19 O14 125.3(2) . . ? O13 C19 C11 123.12(19) . . ? O14 C19 C11 111.61(16) . . ? O2 N1 O1 124.3(2) . . ? O2 N1 C1 118.42(19) . . ? O1 N1 C1 117.27(18) . . ? O11 N11 O12 123.77(19) . . ? O11 N11 C11 118.75(18) . . ? O12 N11 C11 117.48(18) . . ? C9 O4 C10 116.73(17) . . ? C19 O14 C20 116.82(17) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.187 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.040