data_global _journal_coden_Cambridge ? loop_ _publ_author_name 'Frances Heaney' 'Desmond Cunningham' 'Julie Fenlon' 'Patrick McArdle' _publ_contact_author_name 'Dr Frances Heaney' _publ_contact_author_address ; Department of Chemistry The National University of Ireland Maynooth REPUBLIC OF IRELAND ; _publ_contact_author_email MARY.F.HEANEY@MAY.IE _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; a-Keto amides as precursors to heterocycles - generation of and cycloaddition to piperazine-5-one nitrones. ; data_11c _database_code_CSD 197234 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N O5' _chemical_formula_weight 381.41 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 15.243(6) _cell_length_b 8.697(4) _cell_length_c 15.245(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.21(4) _cell_angle_gamma 90.00 _cell_volume 1919.8(17) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.094 _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 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Marresearch image plate' _diffrn_measurement_method '180 mm image plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3086 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 20.90 _reflns_number_total 1796 _reflns_number_gt 1310 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Marresearch MarControl software' _computing_cell_refinement 'XDS (W.Kabsch, 2000)' _computing_data_reduction 'XDS (W.Kabsch, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0731P)^2^+1.7815P] 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 1796 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0918 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.1726 _refine_ls_wR_factor_gt 0.1562 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 -0.0013(3) 0.2181(4) 0.9660(2) 0.0582(11) Uani 1 1 d . . . O13 O 0.2247(3) 0.1546(4) 0.9734(2) 0.0525(10) Uani 1 1 d . . . N1 N 0.0536(3) 0.3195(5) 0.9278(3) 0.0481(12) Uani 1 1 d . . . H1 H 0.005(5) 0.383(7) 0.893(4) 0.09(2) Uiso 1 1 d . . . C3A C -0.0062(4) 0.1114(6) 0.8212(4) 0.0612(17) Uani 1 1 d . . . H3A H -0.0432 0.1389 0.7581 0.080 Uiso 1 1 calc R . . C6A C 0.0761(4) 0.2185(5) 0.8599(3) 0.0403(13) Uani 1 1 d . . . O21 O 0.6273(3) -0.0246(5) 0.9003(3) 0.0710(13) Uani 1 1 d . . . H21 H 0.671(4) -0.054(8) 0.939(4) 0.092 Uiso 1 1 calc R . . O22 O 0.7005(3) 0.0319(4) 0.5692(3) 0.0637(12) Uani 1 1 d . . . H22 H 0.667(4) 0.099(7) 0.536(3) 0.083 Uiso 1 1 calc R . . O26 O 0.8783(4) -0.0813(7) 0.5923(4) 0.111(2) Uani 1 1 d . . . H26 H 0.825(6) -0.031(8) 0.570(5) 0.144 Uiso 1 1 calc R . . C3 C -0.0591(4) 0.1313(7) 0.8897(4) 0.0649(16) Uani 1 1 d . . . H3B H -0.1166 0.1857 0.8612 0.084 Uiso 1 1 calc R . . H3C H -0.0734 0.0319 0.9106 0.084 Uiso 1 1 calc R . . C4 C 0.0414(6) -0.0473(7) 0.8260(5) 0.087(2) Uani 1 1 d . . . H4A H 0.0046 -0.1274 0.8417 0.113 Uiso 1 1 calc R . . H4B H 0.0500 -0.0724 0.7673 0.113 Uiso 1 1 calc R . . C5 C 0.1280(4) -0.0324(5) 0.8962(3) 0.0389(13) Uani 1 1 d . . . C6 C 0.1524(4) 0.1106(6) 0.9167(3) 0.0447(14) Uani 1 1 d . . . C7 C 0.1100(4) 0.3163(5) 0.7947(3) 0.0417(13) Uani 1 1 d . . . C8 C 0.0737(4) 0.3026(7) 0.6999(3) 0.0615(16) Uani 1 1 d . . . H8 H 0.0301 0.2270 0.6742 0.080 Uiso 1 1 calc R . . C9 C 0.1028(5) 0.4025(8) 0.6429(4) 0.077(2) Uani 1 1 d . . . H9 H 0.0765 0.3955 0.5792 0.101 Uiso 1 1 calc R . . C10 C 0.1683(5) 0.5086(7) 0.6787(5) 0.072(2) Uani 1 1 d . . . H10 H 0.1868 0.5746 0.6397 0.093 Uiso 1 1 calc R . . C11 C 0.2076(5) 0.5197(7) 0.7720(5) 0.077(2) Uani 1 1 d . . . H11 H 0.2545 0.5906 0.7968 0.100 Uiso 1 1 calc R . . C12 C 0.1775(5) 0.4249(6) 0.8297(4) 0.0685(19) Uani 1 1 d . . . H12 H 0.2033 0.4348 0.8933 0.089 Uiso 1 1 calc R . . C14 C 0.1828(5) -0.1646(7) 0.9342(5) 0.096(3) Uani 1 1 d . . . H14A H 0.2077 -0.2076 0.8889 0.134 Uiso 1 1 calc R . . H14B H 0.1450 -0.2399 0.9512 0.134 Uiso 1 1 calc R . . H14C H 0.2325 -0.1349 0.9878 0.134 Uiso 1 1 calc R . . C15 C 0.6462(4) -0.0134(6) 0.8184(3) 0.0505(14) Uani 1 1 d . . . C16 C 0.7191(4) -0.0899(6) 0.8022(4) 0.0496(14) Uani 1 1 d . . . H16 H 0.7571 -0.1524 0.8480 0.064 Uiso 1 1 calc R . . C17 C 0.7362(4) -0.0747(5) 0.7194(4) 0.0498(14) Uani 1 1 d . . . H17 H 0.7852 -0.1274 0.7091 0.065 Uiso 1 1 calc R . . C18 C 0.6807(4) 0.0186(5) 0.6513(3) 0.0440(14) Uani 1 1 d . . . C19 C 0.6071(4) 0.0957(5) 0.6664(3) 0.0456(14) Uani 1 1 d . . . H19 H 0.5689 0.1580 0.6207 0.059 Uiso 1 1 calc R . . C20 C 0.5911(4) 0.0789(6) 0.7503(4) 0.0518(15) Uani 1 1 d . . . H20 H 0.5420 0.1312 0.7607 0.067 Uiso 1 1 calc R . . C23 C 0.9369(4) -0.0376(7) 0.5440(4) 0.0618(16) Uani 1 1 d . . . C24 C 0.9241(4) 0.0918(7) 0.4913(4) 0.0673(17) Uani 1 1 d . . . H24 H 0.8731 0.1545 0.4852 0.087 Uiso 1 1 calc R . . C25 C 0.9882(5) 0.1293(7) 0.4468(4) 0.076(2) Uani 1 1 d . . . H25 H 0.9799 0.2174 0.4105 0.099 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 0.055(3) 0.069(2) 0.055(2) 0.005(2) 0.024(2) -0.009(2) O13 0.049(3) 0.056(2) 0.045(2) 0.0054(19) 0.004(2) 0.013(2) N1 0.052(3) 0.050(3) 0.045(3) 0.002(2) 0.021(3) -0.004(3) C3A 0.068(4) 0.068(4) 0.045(3) -0.006(3) 0.014(3) -0.030(3) C6A 0.043(3) 0.044(3) 0.032(3) -0.002(2) 0.007(3) -0.010(3) O21 0.064(3) 0.105(3) 0.050(2) 0.023(2) 0.025(2) 0.024(3) O22 0.075(3) 0.070(3) 0.053(2) 0.0156(19) 0.029(2) 0.022(2) O26 0.086(4) 0.147(5) 0.119(4) 0.051(3) 0.061(4) 0.032(3) C3 0.052(4) 0.070(4) 0.068(4) 0.009(3) 0.011(4) -0.014(3) C4 0.124(7) 0.057(4) 0.098(5) -0.033(4) 0.062(6) -0.047(4) C5 0.059(4) 0.010(3) 0.054(3) -0.010(2) 0.028(3) -0.007(3) C6 0.052(4) 0.053(4) 0.032(3) 0.003(3) 0.017(3) 0.005(3) C7 0.041(3) 0.044(3) 0.038(3) 0.003(2) 0.009(3) -0.004(3) C8 0.064(4) 0.079(4) 0.037(3) 0.005(3) 0.010(3) -0.014(3) C9 0.071(5) 0.116(6) 0.044(4) 0.014(4) 0.017(4) 0.000(5) C10 0.094(6) 0.065(4) 0.072(5) 0.017(3) 0.048(5) 0.000(4) C11 0.094(6) 0.067(4) 0.080(5) -0.003(4) 0.044(5) -0.023(4) C12 0.094(5) 0.064(4) 0.060(4) 0.004(3) 0.043(4) -0.019(4) C14 0.125(7) 0.050(4) 0.144(7) -0.003(4) 0.087(7) 0.007(4) C15 0.049(4) 0.056(3) 0.045(3) 0.006(3) 0.012(3) 0.003(3) C16 0.041(3) 0.054(3) 0.048(3) 0.014(3) 0.006(3) 0.012(3) C17 0.048(4) 0.046(3) 0.056(4) 0.005(3) 0.016(3) 0.013(3) C18 0.055(4) 0.039(3) 0.040(3) 0.005(3) 0.017(3) 0.000(3) C19 0.052(4) 0.034(3) 0.048(3) 0.007(2) 0.011(3) 0.014(3) C20 0.055(4) 0.051(3) 0.051(3) 0.004(3) 0.018(3) 0.009(3) C23 0.058(4) 0.073(4) 0.058(4) 0.007(3) 0.024(4) 0.014(4) C24 0.052(4) 0.082(5) 0.066(4) -0.006(4) 0.016(4) 0.014(3) C25 0.079(5) 0.079(4) 0.073(4) 0.009(4) 0.028(5) 0.010(4) _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 C3 1.435(6) . ? O2 N1 1.456(5) . ? O13 C6 1.230(6) . ? N1 C6A 1.476(6) . ? C3A C3 1.516(7) . ? C3A C6A 1.526(7) . ? C3A C4 1.550(9) . ? C6A C7 1.517(6) . ? C6A C6 1.534(7) . ? O21 C15 1.369(5) . ? O22 C18 1.382(5) . ? O26 C23 1.376(6) . ? C4 C5 1.422(9) . ? C5 C6 1.308(7) . ? C5 C14 1.433(8) . ? C7 C12 1.376(8) . ? C7 C8 1.381(7) . ? C8 C9 1.396(7) . ? C9 C10 1.343(9) . ? C10 C11 1.364(9) . ? C11 C12 1.385(7) . ? C15 C20 1.373(7) . ? C15 C16 1.382(7) . ? C16 C17 1.373(6) . ? C17 C18 1.379(7) . ? C18 C19 1.387(7) . ? C19 C20 1.381(6) . ? C23 C24 1.361(8) . ? C23 C25 1.364(8) 3_756 ? C24 C25 1.392(8) . ? C25 C23 1.364(8) 3_756 ? 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 C3 O2 N1 106.2(3) . . ? O2 N1 C6A 102.0(4) . . ? C3 C3A C6A 102.3(4) . . ? C3 C3A C4 114.2(4) . . ? C6A C3A C4 102.1(5) . . ? N1 C6A C7 109.1(4) . . ? N1 C6A C3A 107.0(4) . . ? C7 C6A C3A 119.7(4) . . ? N1 C6A C6 105.7(4) . . ? C7 C6A C6 111.0(4) . . ? C3A C6A C6 103.4(4) . . ? O2 C3 C3A 107.1(4) . . ? C5 C4 C3A 105.4(4) . . ? C6 C5 C4 113.2(5) . . ? C6 C5 C14 125.5(6) . . ? C4 C5 C14 121.2(5) . . ? O13 C6 C5 126.1(5) . . ? O13 C6 C6A 124.1(5) . . ? C5 C6 C6A 109.7(5) . . ? C12 C7 C8 118.1(5) . . ? C12 C7 C6A 119.8(4) . . ? C8 C7 C6A 122.1(5) . . ? C7 C8 C9 119.8(6) . . ? C10 C9 C8 121.0(6) . . ? C9 C10 C11 120.1(5) . . ? C10 C11 C12 119.7(6) . . ? C7 C12 C11 121.2(6) . . ? O21 C15 C20 118.6(4) . . ? O21 C15 C16 122.6(5) . . ? C20 C15 C16 118.8(4) . . ? C17 C16 C15 120.8(5) . . ? C16 C17 C18 120.0(5) . . ? C17 C18 O22 118.3(4) . . ? C17 C18 C19 119.8(4) . . ? O22 C18 C19 121.9(5) . . ? C20 C19 C18 119.2(5) . . ? C15 C20 C19 121.2(5) . . ? C24 C23 C25 120.3(5) . 3_756 ? C24 C23 O26 123.2(5) . . ? C25 C23 O26 116.5(6) 3_756 . ? C23 C24 C25 119.3(6) . . ? C23 C25 C24 120.4(5) 3_756 . ? _diffrn_measured_fraction_theta_max 0.881 _diffrn_reflns_theta_full 20.90 _diffrn_measured_fraction_theta_full 0.881 _refine_diff_density_max 0.168 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.047 data_21b _database_code_CSD 197235 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 N2 O4' _chemical_formula_weight 288.30 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.4604(16) _cell_length_b 19.740(2) _cell_length_c 16.800(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2805.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.100 _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 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Marresearch image plate' _diffrn_measurement_method '180 mm image plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7213 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 20.88 _reflns_number_total 1459 _reflns_number_gt 1311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Marresearch MarControl software' _computing_cell_refinement 'XDS (W.Kabsch, 2000)' _computing_data_reduction 'XDS (W.Kabsch, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0712P)^2^+1.3161P] 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 1459 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.27138(19) 0.26017(8) 0.45797(9) 0.0322(5) Uani 1 1 d . . . O19 O 0.0751(2) 0.04493(8) 0.41407(10) 0.0371(5) Uani 1 1 d . . . O17 O 0.2253(2) 0.36586(8) 0.36861(10) 0.0459(6) Uani 1 1 d . . . O16 O 0.0427(3) 0.31443(9) 0.29371(12) 0.0495(6) Uani 1 1 d . . . N5 N 0.0888(3) 0.08132(11) 0.54083(12) 0.0344(6) Uani 1 1 d . . . C3A C 0.2284(3) 0.14463(11) 0.43603(13) 0.0250(6) Uani 1 1 d . . . N8 N 0.2710(2) 0.19421(9) 0.49977(11) 0.0257(6) Uani 1 1 d . . . C2 C 0.1802(3) 0.25145(12) 0.39105(14) 0.0278(6) Uani 1 1 d . . . C3 C 0.1458(3) 0.18798(12) 0.37522(14) 0.0280(6) Uani 1 1 d . . . H3 H 0.0819 0.1726 0.3339 0.036 Uiso 1 1 calc R . . C4 C 0.1217(3) 0.08590(12) 0.46422(15) 0.0269(6) Uani 1 1 d . . . C6 C 0.1352(3) 0.13170(12) 0.59927(15) 0.0356(7) Uani 1 1 d . . . H6A H 0.2362 0.1192 0.6222 0.046 Uiso 1 1 calc R . . H6B H 0.0576 0.1330 0.6418 0.046 Uiso 1 1 calc R . . C7 C 0.1479(3) 0.20071(12) 0.56159(14) 0.0293(6) Uani 1 1 d . . . H7 H 0.0469 0.2131 0.5370 0.038 Uiso 1 1 calc R . . C9 C 0.3817(3) 0.11215(11) 0.40491(14) 0.0252(6) Uani 1 1 d . . . C10 C 0.4949(3) 0.09106(12) 0.45830(15) 0.0365(7) Uani 1 1 d . . . H10 H 0.4780 0.0974 0.5125 0.047 Uiso 1 1 calc R . . C11 C 0.6333(3) 0.06057(13) 0.43295(17) 0.0437(8) Uani 1 1 d . . . H11 H 0.7089 0.0471 0.4699 0.057 Uiso 1 1 calc R . . C12 C 0.6589(3) 0.05029(13) 0.35317(17) 0.0423(8) Uani 1 1 d . . . H12 H 0.7519 0.0300 0.3358 0.055 Uiso 1 1 calc R . . C13 C 0.5463(3) 0.07018(12) 0.29921(16) 0.0390(7) Uani 1 1 d . . . H13 H 0.5624 0.0625 0.2452 0.051 Uiso 1 1 calc R . . C14 C 0.4083(3) 0.10166(12) 0.32461(15) 0.0323(7) Uani 1 1 d . . . H14 H 0.3336 0.1157 0.2875 0.042 Uiso 1 1 calc R . . C15 C 0.1402(3) 0.31298(12) 0.34552(16) 0.0332(7) Uani 1 1 d . . . C18 C 0.1952(5) 0.42850(13) 0.3268(2) 0.0696(11) Uani 1 1 d . . . H18A H 0.2381 0.4257 0.2740 0.090 Uiso 1 1 calc R . . H18B H 0.2442 0.4653 0.3548 0.090 Uiso 1 1 calc R . . H18C H 0.0833 0.4361 0.3238 0.090 Uiso 1 1 calc R . . C20 C 0.1950(3) 0.25383(13) 0.62213(15) 0.0419(7) Uani 1 1 d . . . H20A H 0.2911 0.2403 0.6480 0.054 Uiso 1 1 calc R . . H20B H 0.1127 0.2585 0.6611 0.054 Uiso 1 1 calc R . . H20C H 0.2110 0.2964 0.5957 0.054 Uiso 1 1 calc R . . H5 H 0.033(4) 0.0457(14) 0.5552(16) 0.045(8) Uiso 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 O1 0.0343(10) 0.0233(10) 0.0391(11) 0.0035(8) -0.0043(9) -0.0067(7) O19 0.0426(11) 0.0297(10) 0.0391(11) -0.0042(9) 0.0037(9) -0.0115(8) O17 0.0649(14) 0.0222(11) 0.0505(12) 0.0072(8) -0.0125(10) -0.0058(10) O16 0.0576(13) 0.0404(11) 0.0505(12) 0.0128(9) -0.0173(12) -0.0049(10) N5 0.0407(14) 0.0287(13) 0.0339(14) 0.0004(11) 0.0069(11) -0.0113(11) C3A 0.0234(14) 0.0224(14) 0.0293(13) 0.0014(11) -0.0003(11) -0.0005(10) N8 0.0265(12) 0.0193(11) 0.0313(12) 0.0017(9) 0.0015(9) -0.0004(8) C2 0.0243(13) 0.0265(16) 0.0325(14) 0.0046(12) -0.0010(12) 0.0007(11) C3 0.0274(15) 0.0259(16) 0.0308(14) 0.0009(11) -0.0018(11) -0.0014(11) C4 0.0237(14) 0.0217(13) 0.0353(17) -0.0009(13) 0.0009(12) 0.0023(11) C6 0.0385(16) 0.0362(16) 0.0321(14) -0.0003(12) 0.0066(12) -0.0027(12) C7 0.0258(15) 0.0304(14) 0.0318(14) -0.0038(12) 0.0015(12) 0.0023(11) C9 0.0270(14) 0.0187(13) 0.0298(14) 0.0032(11) 0.0046(12) -0.0024(11) C10 0.0372(17) 0.0372(15) 0.0352(15) 0.0039(12) 0.0079(14) 0.0106(13) C11 0.0381(18) 0.0441(17) 0.0488(19) 0.0087(14) 0.0021(15) 0.0172(14) C12 0.0352(16) 0.0337(16) 0.058(2) 0.0010(14) 0.0159(16) 0.0102(13) C13 0.0429(18) 0.0331(14) 0.0410(16) -0.0036(13) 0.0164(15) -0.0045(14) C14 0.0316(16) 0.0301(13) 0.0350(16) 0.0002(11) 0.0011(12) -0.0058(12) C15 0.0375(17) 0.0275(16) 0.0347(16) 0.0000(12) 0.0057(15) -0.0004(13) C18 0.109(3) 0.0261(16) 0.074(2) 0.0154(16) -0.025(2) -0.0098(18) C20 0.0493(18) 0.0369(16) 0.0396(16) -0.0070(13) 0.0011(14) 0.0055(13) _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 C2 1.374(3) . ? O1 N8 1.479(2) . ? O19 C4 1.233(3) . ? O17 C15 1.326(3) . ? O17 C18 1.445(3) . ? O16 C15 1.199(3) . ? N5 C4 1.320(3) . ? N5 C6 1.451(3) . ? C3A N8 1.495(3) . ? C3A C3 1.505(3) . ? C3A C9 1.538(3) . ? C3A C4 1.544(3) . ? N8 C7 1.476(3) . ? C2 C3 1.314(3) . ? C2 C15 1.475(4) . ? C6 C7 1.506(4) . ? C7 C20 1.514(3) . ? C9 C10 1.377(3) . ? C9 C14 1.383(4) . ? C10 C11 1.384(4) . ? C11 C12 1.373(4) . ? C12 C13 1.372(4) . ? C13 C14 1.390(4) . ? 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 O1 N8 106.09(16) . . ? C15 O17 C18 115.8(2) . . ? C4 N5 C6 123.8(2) . . ? N8 C3A C3 103.06(17) . . ? N8 C3A C9 108.27(18) . . ? C3 C3A C9 113.45(19) . . ? N8 C3A C4 114.38(18) . . ? C3 C3A C4 111.31(19) . . ? C9 C3A C4 106.51(18) . . ? C7 N8 O1 105.01(16) . . ? C7 N8 C3A 113.01(18) . . ? O1 N8 C3A 103.69(15) . . ? C3 C2 O1 114.2(2) . . ? C3 C2 C15 129.0(2) . . ? O1 C2 C15 116.8(2) . . ? C2 C3 C3A 107.6(2) . . ? O19 C4 N5 123.6(2) . . ? O19 C4 C3A 118.0(2) . . ? N5 C4 C3A 118.3(2) . . ? N5 C6 C7 110.8(2) . . ? N8 C7 C6 105.53(19) . . ? N8 C7 C20 110.3(2) . . ? C6 C7 C20 111.3(2) . . ? C10 C9 C14 118.5(2) . . ? C10 C9 C3A 119.4(2) . . ? C14 C9 C3A 122.1(2) . . ? C9 C10 C11 121.3(2) . . ? C12 C11 C10 119.9(3) . . ? C13 C12 C11 119.6(2) . . ? C12 C13 C14 120.6(2) . . ? C9 C14 C13 120.2(2) . . ? O16 C15 O17 124.5(2) . . ? O16 C15 C2 123.6(2) . . ? O17 C15 C2 111.8(2) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 20.88 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.227 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.076