data_q24b _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H9 N3 O2' _chemical_formula_weight 143.15 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 Orthorhombic _symmetry_space_group_name_H-M Pbam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' _cell_length_a 14.1588(4) _cell_length_b 7.1036(2) _cell_length_c 13.5770(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1365.55(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4464 _cell_measurement_theta_min 6.23 _cell_measurement_theta_max 68.91 _exptl_crystal_description 'Rectangular parallelepiped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.927 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6653 _exptl_absorpt_correction_T_max 0.7532 _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 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer x-ray optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8598 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0105 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 69.33 _reflns_number_total 1323 _reflns_number_gt 1217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0507P)^2^+0.9271P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1323 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _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 0.59452(8) 0.31614(17) 0.15408(8) 0.0244(3) Uani 1 1 d . . . H2O H 0.6062(18) 0.389(4) 0.211(2) 0.061(8) Uiso 1 1 d . . . N1 N 0.50063(15) 0.2416(3) 0.0000 0.0194(4) Uani 1 2 d S . . H2N H 0.556(2) 0.292(4) 0.0000 0.033(8) Uiso 1 2 d S . . N2 N 0.49923(10) 0.26089(19) 0.17063(9) 0.0220(3) Uani 1 1 d . . . C1 C 0.45698(12) 0.2248(2) 0.09011(10) 0.0185(4) Uani 1 1 d . . . C2 C 0.35516(12) 0.1625(2) 0.09181(12) 0.0233(4) Uani 1 1 d . . . H2A H 0.3527(15) 0.025(3) 0.0933(13) 0.029(5) Uiso 1 1 d . . . H2B H 0.3262(16) 0.206(3) 0.1527(16) 0.033(5) Uiso 1 1 d . . . C3 C 0.30453(17) 0.2339(3) 0.0000 0.0242(5) Uani 1 2 d S . . H3A H 0.304(2) 0.367(4) 0.0000 0.027(7) Uiso 1 2 d S . . H3B H 0.240(2) 0.190(4) 0.0000 0.028(7) Uiso 1 2 d S . . O11 O 0.59148(9) 0.69299(16) 0.65406(8) 0.0238(3) Uani 1 1 d . . . H12O H 0.5574(18) 0.722(3) 0.706(2) 0.045(7) Uiso 1 1 d . . . N11 N 0.62347(13) 0.5029(3) 0.5000 0.0190(4) Uani 1 2 d S . . H12N H 0.602(2) 0.617(5) 0.5000 0.032(8) Uiso 1 2 d S . . N12 N 0.61686(10) 0.5023(2) 0.67115(10) 0.0225(3) Uani 1 1 d . . . C11 C 0.63311(11) 0.4164(2) 0.59002(10) 0.0193(4) Uani 1 1 d . . . C12 C 0.66390(13) 0.2146(2) 0.59196(12) 0.0242(4) Uani 1 1 d . . . H12A H 0.6403(15) 0.159(3) 0.6515(16) 0.032(5) Uiso 1 1 d . . . H12B H 0.7304(16) 0.210(3) 0.5926(14) 0.030(5) Uiso 1 1 d . . . C13 C 0.62955(18) 0.1118(4) 0.5000 0.0278(6) Uani 1 2 d S . . H13A H 0.6496(19) -0.014(4) 0.5000 0.019(6) Uiso 1 2 d S . . H13B H 0.558(2) 0.107(4) 0.5000 0.028(7) Uiso 1 2 d S . . 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 0.0239(6) 0.0315(7) 0.0178(6) -0.0052(5) 0.0004(4) -0.0024(5) N1 0.0208(9) 0.0231(10) 0.0142(9) 0.000 0.000 -0.0015(8) N2 0.0239(7) 0.0253(7) 0.0169(7) -0.0022(5) 0.0035(5) -0.0003(6) C1 0.0244(8) 0.0161(8) 0.0150(8) -0.0008(6) 0.0032(6) 0.0031(6) C2 0.0256(8) 0.0226(9) 0.0217(9) -0.0022(6) 0.0052(6) -0.0016(7) C3 0.0214(12) 0.0204(12) 0.0308(13) 0.000 0.000 0.0007(10) O11 0.0321(7) 0.0227(6) 0.0165(6) 0.0003(4) 0.0050(5) 0.0019(5) N11 0.0226(10) 0.0193(9) 0.0151(9) 0.000 0.000 0.0014(8) N12 0.0267(7) 0.0232(7) 0.0178(7) 0.0032(6) 0.0027(5) 0.0014(6) C11 0.0177(7) 0.0240(8) 0.0161(8) 0.0030(6) 0.0013(5) -0.0015(6) C12 0.0275(9) 0.0246(9) 0.0204(9) 0.0054(6) 0.0023(6) 0.0030(7) C13 0.0301(13) 0.0204(12) 0.0327(13) 0.000 0.000 0.0000(10) _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 N2 1.4229(18) . ? O1 H2O 0.94(3) . ? N1 C1 1.3758(18) 6 ? N1 C1 1.3758(18) . ? N1 H2N 0.86(3) . ? N2 C1 1.272(2) . ? C1 C2 1.508(2) . ? C2 C3 1.525(2) . ? C2 H2A 0.98(2) . ? C2 H2B 0.97(2) . ? C3 C2 1.525(2) 6 ? C3 H3A 0.95(3) . ? C3 H3B 0.97(3) . ? O11 N12 1.4202(18) . ? O11 H12O 0.88(3) . ? N11 C11 1.3749(17) . ? N11 C11 1.3750(17) 6_556 ? N11 H12N 0.87(3) . ? N12 C11 1.280(2) . ? C11 C12 1.498(2) . ? C12 C13 1.526(2) . ? C12 H12A 0.96(2) . ? C12 H12B 0.94(2) . ? C13 C12 1.526(2) 6_556 ? C13 H13A 0.94(3) . ? C13 H13B 1.01(3) . ? 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 N2 O1 H2O 100.9(16) . . ? C1 N1 C1 125.5(2) 6 . ? C1 N1 H2N 116.4(3) 6 . ? C1 N1 H2N 116.4(3) . . ? C1 N2 O1 111.45(12) . . ? N2 C1 N1 122.37(16) . . ? N2 C1 C2 119.69(13) . . ? N1 C1 C2 117.94(14) . . ? C1 C2 C3 109.82(14) . . ? C1 C2 H2A 109.2(13) . . ? C3 C2 H2A 109.4(11) . . ? C1 C2 H2B 108.8(13) . . ? C3 C2 H2B 113.1(13) . . ? H2A C2 H2B 106.4(17) . . ? C2 C3 C2 109.67(19) 6 . ? C2 C3 H3A 109.5(9) 6 . ? C2 C3 H3A 109.5(9) . . ? C2 C3 H3B 109.8(9) 6 . ? C2 C3 H3B 109.8(9) . . ? H3A C3 H3B 108(2) . . ? N12 O11 H12O 103.4(16) . . ? C11 N11 C11 125.5(2) . 6_556 ? C11 N11 H12N 116.97(18) . . ? C11 N11 H12N 116.97(18) 6_556 . ? C11 N12 O11 111.09(12) . . ? N12 C11 N11 122.24(16) . . ? N12 C11 C12 119.57(13) . . ? N11 C11 C12 118.19(14) . . ? C11 C12 C13 110.54(15) . . ? C11 C12 H12A 107.9(13) . . ? C13 C12 H12A 112.4(13) . . ? C11 C12 H12B 108.8(13) . . ? C13 C12 H12B 108.1(12) . . ? H12A C12 H12B 109.2(18) . . ? C12 C13 C12 109.8(2) . 6_556 ? C12 C13 H13A 111.1(8) . . ? C12 C13 H13A 111.1(8) 6_556 . ? C12 C13 H13B 109.6(8) . . ? C12 C13 H13B 109.6(8) 6_556 . ? H13A C13 H13B 106(2) . . ? 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 N2 C1 N1 -0.8(2) . . . . ? O1 N2 C1 C2 179.65(13) . . . . ? C1 N1 C1 N2 -172.62(13) 6 . . . ? C1 N1 C1 C2 6.9(3) 6 . . . ? N2 C1 C2 C3 147.40(16) . . . . ? N1 C1 C2 C3 -32.2(2) . . . . ? C1 C2 C3 C2 57.3(2) . . . 6 ? O11 N12 C11 N11 -1.7(2) . . . . ? O11 N12 C11 C12 178.16(13) . . . . ? C11 N11 C11 N12 -175.11(12) 6_556 . . . ? C11 N11 C11 C12 5.0(3) 6_556 . . . ? N12 C11 C12 C13 149.50(16) . . . . ? N11 C11 C12 C13 -30.6(2) . . . . ? C11 C12 C13 C12 55.6(2) . . . 6_556 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H2O N12 0.94(3) 1.80(3) 2.7350(17) 171(2) 6_556 O11 H12O N2 0.88(3) 1.86(3) 2.7243(17) 167(2) 5_666 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 69.33 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.415 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.045