# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/266 ### Crystallographic supplementary information: Wentrup et al, J.C.S. Perkin 2 # Compound 2a data_bw3n _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 N2 O2' _chemical_formula_weight 176.17 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 'P 21/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 9.116(6) _cell_length_b 5.0660(10) _cell_length_c 17.13(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.97(3) _cell_angle_gamma 90.00 _cell_volume 789.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_description yellow _exptl_crystal_colour needle _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Enraf Nonius CAD4' _diffrn_measurement_method '\w-2q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% ? _diffrn_reflns_number 1494 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.1254 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 24.96 _reflns_number_total 1380 _reflns_number_gt 514 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4' _computing_cell_refinement 'SET4 in CAD4' _computing_data_reduction 'XTAL3.2' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'SHELXL-97' _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 w=1/[\s^2^(Fo^2^)+(0.0957P)^2^+0.0000P] 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 1380 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1890 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1880 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.916 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3600(4) 0.2341(7) 0.9779(2) 0.0380(11) Uani 1 d . . . H1 H 0.4049 0.1030 0.9584 0.046 Uiso 1 calc R . . C1 C 0.3618(6) 0.5965(11) 1.1695(3) 0.0525(15) Uani 1 d . . . H1A H 0.4384 0.4853 1.1924 0.079 Uiso 1 calc R . . H1B H 0.2763 0.5815 1.1989 0.079 Uiso 1 calc R . . H1C H 0.3948 0.7765 1.1702 0.079 Uiso 1 calc R . . C2 C 0.4003(5) 0.3055(10) 1.0550(3) 0.0364(12) Uani 1 d . . . O2 O 0.5032(4) 0.1760(7) 1.09007(19) 0.0465(10) Uani 1 d . . . C3 C 0.3241(5) 0.5127(10) 1.0866(3) 0.0373(12) Uani 1 d . . . C4 C 0.2143(5) 0.6529(10) 1.0434(3) 0.0359(12) Uani 1 d . . . O4 O 0.1419(4) 0.8413(7) 1.06456(19) 0.0511(10) Uani 1 d . . . N5 N 0.1838(4) 0.5622(7) 0.9625(2) 0.0344(10) Uani 1 d . . . C6 C 0.0776(5) 0.6925(10) 0.9171(3) 0.0435(14) Uani 1 d . . . H6 H 0.0293 0.8344 0.9383 0.052 Uiso 1 calc R . . C7 C 0.0411(6) 0.6207(11) 0.8426(3) 0.0495(15) Uani 1 d . . . H7 H -0.0307 0.7129 0.8125 0.059 Uiso 1 calc R . . C8 C 0.1131(6) 0.4044(10) 0.8109(3) 0.0459(14) Uani 1 d . . . H8 H 0.0869 0.3483 0.7602 0.055 Uiso 1 calc R . . C9 C 0.2208(5) 0.2777(10) 0.8548(3) 0.0429(14) Uani 1 d . . . H9 H 0.2713 0.1387 0.8335 0.052 Uiso 1 calc R . . C10 C 0.2560(5) 0.3564(10) 0.9324(3) 0.0355(13) Uani 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 N1 0.038(2) 0.033(2) 0.043(2) -0.0022(19) 0.002(2) 0.009(2) C1 0.056(4) 0.051(4) 0.050(3) -0.001(3) 0.001(3) 0.006(3) C2 0.039(3) 0.035(3) 0.036(3) 0.003(2) 0.006(2) 0.000(3) O2 0.045(2) 0.043(2) 0.051(2) 0.0006(18) -0.0057(17) 0.013(2) C3 0.038(3) 0.039(3) 0.034(3) -0.002(2) 0.002(2) 0.003(3) C4 0.038(3) 0.031(3) 0.039(3) -0.001(2) 0.009(2) 0.004(3) O4 0.056(2) 0.042(2) 0.056(2) -0.0033(19) 0.0050(18) 0.016(2) N5 0.030(2) 0.029(2) 0.043(2) 0.0032(19) 0.0014(19) 0.002(2) C6 0.039(3) 0.040(3) 0.052(3) 0.015(3) 0.002(3) 0.007(3) C7 0.049(3) 0.052(4) 0.046(3) 0.017(3) -0.008(3) 0.001(3) C8 0.048(3) 0.045(3) 0.043(3) 0.007(3) -0.003(3) -0.007(3) C9 0.049(3) 0.039(3) 0.041(3) -0.002(2) 0.004(3) -0.003(3) C10 0.033(3) 0.028(3) 0.045(3) 0.005(2) 0.005(2) 0.000(2) _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 N1 C10 1.337(6) . ? N1 C2 1.394(6) . ? N1 H1 0.8600 . ? C1 C3 1.499(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O2 1.262(5) . ? C2 C3 1.389(6) . ? C3 C4 1.396(6) . ? C4 O4 1.229(5) . ? C4 N5 1.469(6) . ? N5 C10 1.354(6) . ? N5 C6 1.369(6) . ? C6 C7 1.347(7) . ? C6 H6 0.9300 . ? C7 C8 1.405(7) . ? C7 H7 0.9300 . ? C8 C9 1.356(6) . ? C8 H8 0.9300 . ? C9 C10 1.404(6) . ? C9 H9 0.9300 . ? 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 C10 N1 C2 124.2(4) . . ? C10 N1 H1 117.9 . . ? C2 N1 H1 117.9 . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C3 125.7(4) . . ? O2 C2 N1 117.0(4) . . ? C3 C2 N1 117.3(4) . . ? C2 C3 C4 122.5(5) . . ? C2 C3 C1 119.7(4) . . ? C4 C3 C1 117.8(5) . . ? O4 C4 C3 128.2(5) . . ? O4 C4 N5 116.8(4) . . ? C3 C4 N5 115.0(5) . . ? C10 N5 C6 119.9(4) . . ? C10 N5 C4 122.3(4) . . ? C6 N5 C4 117.8(4) . . ? C7 C6 N5 121.8(5) . . ? C7 C6 H6 119.1 . . ? N5 C6 H6 119.1 . . ? C6 C7 C8 119.0(5) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C9 C8 C7 119.7(5) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.0(5) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? N1 C10 N5 118.6(4) . . ? N1 C10 C9 121.8(5) . . ? N5 C10 C9 119.6(4) . . ? 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 C6 H6 O4 0.93 2.33 2.662(7) 100.6 . C6 H6 O4 0.93 2.26 3.125(6) 153.8 3_577 N1 H1 O2 0.86 1.87 2.726(5) 176.5 3_657 _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.889 _refine_diff_density_max 0.257 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.067 #===END # Compound 3 data_olate _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 N2 O2' _chemical_formula_weight 238.24 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 6.52870(10) _cell_length_b 7.30040(10) _cell_length_c 12.07350(10) _cell_angle_alpha 98.2600(10) _cell_angle_beta 101.0860(10) _cell_angle_gamma 101.8710(10) _cell_volume 542.482(12) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 4409 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 28,21 _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9489 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 'Siemens SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'none' _diffrn_reflns_number 2396 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.21 _reflns_number_total 2396 _reflns_number_gt 2074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART (Siemens, 1994a)' _computing_cell_refinement 'Siemens SMART (Siemens, 1994a)' _computing_data_reduction 'Siemens SHELXTL (Siemens, 1994b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL (Siemens, 1994b)' _computing_publication_material 'Siemens SHELXTL (Siemens, 1994b)' _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 w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.0657P] 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 2396 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.002 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N5 N 0.44237(13) 0.70468(12) 0.06193(7) 0.0229(2) Uani 1 d . . . O2 O 0.80912(11) 0.96997(12) -0.12774(6) 0.0288(2) Uani 1 d . . . C6 C 0.31796(18) 0.62897(16) 0.13204(10) 0.0279(2) Uani 1 d . . . H6 H 0.172(2) 0.587(2) 0.0980(12) 0.038(4) Uiso 1 d . . . N1 N 0.77046(14) 0.85365(13) 0.03134(7) 0.0248(2) Uani 1 d . . . H1 H 0.915(3) 0.912(2) 0.0618(13) 0.043(4) Uiso 1 d . . . O4 O 0.13803(12) 0.62955(13) -0.08250(7) 0.0362(2) Uani 1 d . . . C7 C 0.40966(19) 0.61769(17) 0.24080(10) 0.0312(3) Uani 1 d . . . H7 H 0.319(2) 0.564(2) 0.2852(12) 0.041(4) Uiso 1 d . . . C8 C 0.6345(2) 0.68213(18) 0.28164(10) 0.0327(3) Uani 1 d . . . H8 H 0.702(3) 0.668(2) 0.3602(14) 0.050(4) Uiso 1 d . . . C9 C 0.75697(18) 0.75911(17) 0.21298(9) 0.0291(3) Uani 1 d . . . H9 H 0.909(2) 0.805(2) 0.2352(12) 0.034(3) Uiso 1 d . . . C10 C 0.65805(16) 0.77347(14) 0.10094(9) 0.0235(2) Uani 1 d . . . C2 C 0.68316(16) 0.87599(15) -0.07948(9) 0.0229(2) Uani 1 d . . . C3 C 0.45999(16) 0.79117(15) -0.12627(9) 0.0225(2) Uani 1 d . . . C4 C 0.33042(17) 0.70508(15) -0.05785(9) 0.0249(2) Uani 1 d . . . C11 C 0.36159(16) 0.78968(15) -0.24843(9) 0.0239(2) Uani 1 d . . . C12 C 0.48678(18) 0.79781(18) -0.33055(10) 0.0324(3) Uani 1 d . . . H12 H 0.643(2) 0.807(2) -0.3076(12) 0.042(4) Uiso 1 d . . . C13 C 0.3967(2) 0.7935(2) -0.44473(11) 0.0434(3) Uani 1 d . . . H13 H 0.492(3) 0.801(2) -0.4988(13) 0.050(4) Uiso 1 d . . . C14 C 0.1789(2) 0.7812(3) -0.48111(11) 0.0496(4) Uani 1 d . . . H14 H 0.119(3) 0.781(3) -0.5620(17) 0.069(5) Uiso 1 d . . . C15 C 0.0529(2) 0.7732(2) -0.40163(11) 0.0449(3) Uani 1 d . . . H15 H -0.104(3) 0.765(3) -0.4250(14) 0.059(5) Uiso 1 d . . . C16 C 0.14131(18) 0.77692(18) -0.28679(10) 0.0314(3) Uani 1 d . . . H16 H 0.048(2) 0.774(2) -0.2322(12) 0.035(3) Uiso 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 N5 0.0186(4) 0.0239(4) 0.0252(4) 0.0044(3) 0.0058(3) 0.0020(3) O2 0.0178(4) 0.0381(5) 0.0286(4) 0.0096(3) 0.0051(3) 0.0003(3) C6 0.0233(5) 0.0288(5) 0.0315(5) 0.0066(4) 0.0097(4) 0.0025(4) N1 0.0154(4) 0.0308(5) 0.0260(4) 0.0059(4) 0.0034(3) 0.0018(3) O4 0.0188(4) 0.0491(5) 0.0347(4) 0.0130(4) 0.0034(3) -0.0056(3) C7 0.0310(6) 0.0336(6) 0.0303(6) 0.0094(4) 0.0118(5) 0.0036(5) C8 0.0345(6) 0.0359(6) 0.0272(5) 0.0080(5) 0.0053(5) 0.0075(5) C9 0.0235(5) 0.0334(6) 0.0282(5) 0.0062(4) 0.0026(4) 0.0048(4) C10 0.0193(5) 0.0233(5) 0.0268(5) 0.0028(4) 0.0054(4) 0.0040(4) C2 0.0185(5) 0.0251(5) 0.0249(5) 0.0034(4) 0.0050(4) 0.0053(4) C3 0.0177(5) 0.0249(5) 0.0239(5) 0.0035(4) 0.0048(4) 0.0035(4) C4 0.0196(5) 0.0269(5) 0.0260(5) 0.0037(4) 0.0038(4) 0.0030(4) C11 0.0205(5) 0.0250(5) 0.0240(5) 0.0028(4) 0.0033(4) 0.0033(4) C12 0.0230(5) 0.0453(7) 0.0284(6) 0.0076(5) 0.0062(4) 0.0065(5) C13 0.0335(6) 0.0701(9) 0.0271(6) 0.0109(6) 0.0098(5) 0.0099(6) C14 0.0350(7) 0.0856(11) 0.0252(6) 0.0117(6) 0.0008(5) 0.0125(7) C15 0.0247(6) 0.0740(10) 0.0323(6) 0.0078(6) -0.0006(5) 0.0120(6) C16 0.0217(5) 0.0437(7) 0.0272(5) 0.0043(5) 0.0044(4) 0.0068(5) _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 N5 C10 1.3575(13) . ? N5 C6 1.3770(13) . ? N5 C4 1.4903(13) . ? O2 C2 1.2464(12) . ? C6 C7 1.3558(16) . ? C6 H6 0.929(15) . ? N1 C10 1.3376(13) . ? N1 C2 1.3961(13) . ? N1 H1 0.929(17) . ? O4 C4 1.2225(13) . ? C7 C8 1.4107(17) . ? C7 H7 0.939(16) . ? C8 C9 1.3588(16) . ? C8 H8 0.994(17) . ? C9 C10 1.4108(15) . ? C9 H9 0.951(14) . ? C2 C3 1.4273(14) . ? C3 C4 1.4115(14) . ? C3 C11 1.4887(14) . ? C11 C12 1.4012(15) . ? C11 C16 1.4028(14) . ? C12 C13 1.3839(16) . ? C12 H12 0.989(15) . ? C13 C14 1.3857(19) . ? C13 H13 0.983(16) . ? C14 C15 1.3784(19) . ? C14 H14 0.979(19) . ? C15 C16 1.3897(16) . ? C15 H15 0.999(18) . ? C16 H16 0.977(14) . ? 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 C10 N5 C6 120.83(9) . . ? C10 N5 C4 122.01(9) . . ? C6 N5 C4 117.16(8) . . ? C7 C6 N5 120.48(10) . . ? C7 C6 H6 124.9(9) . . ? N5 C6 H6 114.6(9) . . ? C10 N1 C2 125.13(9) . . ? C10 N1 H1 117.7(9) . . ? C2 N1 H1 116.8(9) . . ? C6 C7 C8 119.58(10) . . ? C6 C7 H7 117.5(9) . . ? C8 C7 H7 122.9(9) . . ? C9 C8 C7 119.94(10) . . ? C9 C8 H8 120.6(10) . . ? C7 C8 H8 119.5(10) . . ? C8 C9 C10 119.64(10) . . ? C8 C9 H9 124.2(8) . . ? C10 C9 H9 116.1(8) . . ? N1 C10 N5 118.56(9) . . ? N1 C10 C9 121.97(9) . . ? N5 C10 C9 119.47(10) . . ? O2 C2 N1 116.22(9) . . ? O2 C2 C3 126.31(9) . . ? N1 C2 C3 117.46(9) . . ? C4 C3 C2 120.45(9) . . ? C4 C3 C11 119.13(9) . . ? C2 C3 C11 120.42(9) . . ? O4 C4 C3 129.37(10) . . ? O4 C4 N5 114.63(9) . . ? C3 C4 N5 116.00(9) . . ? C12 C11 C16 117.22(9) . . ? C12 C11 C3 120.76(9) . . ? C16 C11 C3 122.01(9) . . ? C13 C12 C11 121.35(10) . . ? C13 C12 H12 118.5(8) . . ? C11 C12 H12 120.2(8) . . ? C12 C13 C14 120.66(11) . . ? C12 C13 H13 118.2(9) . . ? C14 C13 H13 121.2(9) . . ? C15 C14 C13 118.88(11) . . ? C15 C14 H14 121.9(11) . . ? C13 C14 H14 119.2(11) . . ? C14 C15 C16 121.01(11) . . ? C14 C15 H15 120.9(10) . . ? C16 C15 H15 118.1(10) . . ? C15 C16 C11 120.87(11) . . ? C15 C16 H16 119.0(8) . . ? C11 C16 H16 120.1(8) . . ? 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 C10 N5 C6 C7 -1.55(17) . . . . ? C4 N5 C6 C7 177.69(10) . . . . ? N5 C6 C7 C8 -0.72(18) . . . . ? C6 C7 C8 C9 1.57(19) . . . . ? C7 C8 C9 C10 -0.19(18) . . . . ? C2 N1 C10 N5 1.11(16) . . . . ? C2 N1 C10 C9 -178.73(10) . . . . ? C6 N5 C10 N1 -176.92(9) . . . . ? C4 N5 C10 N1 3.87(15) . . . . ? C6 N5 C10 C9 2.93(16) . . . . ? C4 N5 C10 C9 -176.28(9) . . . . ? C8 C9 C10 N1 177.80(10) . . . . ? C8 C9 C10 N5 -2.04(17) . . . . ? C10 N1 C2 O2 173.44(9) . . . . ? C10 N1 C2 C3 -6.14(16) . . . . ? O2 C2 C3 C4 -173.40(10) . . . . ? N1 C2 C3 C4 6.14(15) . . . . ? O2 C2 C3 C11 7.55(16) . . . . ? N1 C2 C3 C11 -172.91(9) . . . . ? C2 C3 C4 O4 178.53(11) . . . . ? C11 C3 C4 O4 -2.41(18) . . . . ? C2 C3 C4 N5 -1.67(15) . . . . ? C11 C3 C4 N5 177.39(8) . . . . ? C10 N5 C4 O4 176.32(10) . . . . ? C6 N5 C4 O4 -2.91(15) . . . . ? C10 N5 C4 C3 -3.50(15) . . . . ? C6 N5 C4 C3 177.27(9) . . . . ? C4 C3 C11 C12 -153.38(11) . . . . ? C2 C3 C11 C12 25.68(15) . . . . ? C4 C3 C11 C16 25.51(16) . . . . ? C2 C3 C11 C16 -155.43(11) . . . . ? C16 C11 C12 C13 0.02(18) . . . . ? C3 C11 C12 C13 178.97(12) . . . . ? C11 C12 C13 C14 0.1(2) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C11 0.3(2) . . . . ? C12 C11 C16 C15 -0.20(18) . . . . ? C3 C11 C16 C15 -179.13(12) . . . . ? _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.894 _refine_diff_density_max 0.287 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.040 #===END # Compound 5a data_1611bw2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 N O3' _chemical_formula_weight 177.16 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 'P 2 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 7.6880(10) _cell_length_b 13.3074(9) _cell_length_c 15.144(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.243(9) _cell_angle_gamma 90.00 _cell_volume 1546.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type '\y-scans' _exptl_absorpt_correction_T_min 0.893 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Enraf Nonius CAD4' _diffrn_measurement_method '\w-2q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% ? _diffrn_reflns_number 2925 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_sigmaI/netI 0.2005 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.96 _reflns_number_total 2712 _reflns_number_gt 735 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4' _computing_cell_refinement 'SET4 in CAD4' _computing_data_reduction 'XTAL3.2' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'SHELXL-97' _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 w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.0000P] 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 2712 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2756 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1885 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.929 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O 1.0263(6) 0.8763(3) 0.2145(3) 0.0525(14) Uani 1 d . . . C1A C 1.2867(9) 0.7332(5) 0.0513(4) 0.056(2) Uani 1 d . . . H1A H 1.3437 0.6695 0.0601 0.084 Uiso 1 calc R . . H1B H 1.3727 0.7849 0.0464 0.084 Uiso 1 calc R . . H1C H 1.2128 0.7310 -0.0019 0.084 Uiso 1 calc R . . C2A C 1.1240(9) 0.8549(5) 0.1389(5) 0.050(2) Uani 1 d . . . O2A O 1.1497(7) 0.9274(4) 0.0937(3) 0.0723(17) Uani 1 d . . . C3A C 1.1796(9) 0.7552(5) 0.1280(5) 0.0425(19) Uani 1 d . . . C4A C 1.1364(10) 0.6786(5) 0.1847(5) 0.046(2) Uani 1 d . . . O4A O 1.1709(6) 0.5886(3) 0.1813(3) 0.0578(14) Uani 1 d . . . N5A N 1.0352(7) 0.7101(4) 0.2608(4) 0.0433(16) Uani 1 d . . . C6A C 0.9922(9) 0.6392(5) 0.3199(5) 0.050(2) Uani 1 d . . . H6A H 1.0242 0.5726 0.3113 0.060 Uiso 1 calc R . . C7A C 0.9036(10) 0.6639(5) 0.3908(5) 0.059(2) Uani 1 d . . . H7A H 0.8753 0.6144 0.4309 0.071 Uiso 1 calc R . . C8A C 0.8541(10) 0.7627(6) 0.4048(5) 0.058(2) Uani 1 d . . . H8A H 0.7927 0.7799 0.4537 0.070 Uiso 1 calc R . . C9A C 0.8975(9) 0.8343(5) 0.3449(5) 0.053(2) Uani 1 d . . . H9A H 0.8669 0.9011 0.3529 0.064 Uiso 1 calc R . . C10A C 0.9869(9) 0.8063(5) 0.2727(5) 0.042(2) Uani 1 d . . . O1B O 0.5872(6) 0.6630(3) 0.2336(3) 0.0490(13) Uani 1 d . . . C1B C 0.7728(10) 0.5178(5) 0.0472(5) 0.077(3) Uani 1 d . . . H1D H 0.8961 0.5257 0.0588 0.115 Uiso 1 calc R . . H1E H 0.7331 0.5636 0.0014 0.115 Uiso 1 calc R . . H1F H 0.7481 0.4501 0.0284 0.115 Uiso 1 calc R . . C2B C 0.6727(8) 0.6412(5) 0.1549(4) 0.0407(18) Uani 1 d . . . O2B O 0.7272(6) 0.7149(3) 0.1189(3) 0.0541(14) Uani 1 d . . . C3B C 0.6812(9) 0.5395(5) 0.1293(5) 0.046(2) Uani 1 d . . . C4B C 0.6089(10) 0.4620(6) 0.1762(5) 0.053(2) Uani 1 d . . . O4B O 0.6092(7) 0.3729(3) 0.1619(3) 0.0700(17) Uani 1 d . . . N5B N 0.5242(7) 0.4944(4) 0.2575(4) 0.0405(15) Uani 1 d . . . C6B C 0.4470(9) 0.4228(5) 0.3074(5) 0.054(2) Uani 1 d . . . H6B H 0.4495 0.3559 0.2899 0.064 Uiso 1 calc R . . C7B C 0.3675(9) 0.4479(5) 0.3812(5) 0.053(2) Uani 1 d . . . H7B H 0.3143 0.3986 0.4138 0.063 Uiso 1 calc R . . C8B C 0.3649(9) 0.5485(6) 0.4088(5) 0.052(2) Uani 1 d . . . H8B H 0.3131 0.5664 0.4605 0.062 Uiso 1 calc R . . C9B C 0.4403(9) 0.6198(5) 0.3579(5) 0.049(2) Uani 1 d . . . H9B H 0.4383 0.6870 0.3745 0.059 Uiso 1 calc R . . C10B C 0.5187(8) 0.5919(6) 0.2823(5) 0.0446(19) Uani 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 O1A 0.074(4) 0.025(3) 0.060(3) 0.000(3) 0.017(3) 0.008(2) C1A 0.062(5) 0.039(4) 0.067(5) -0.006(4) 0.007(4) 0.008(4) C2A 0.062(6) 0.036(5) 0.053(5) -0.009(4) 0.010(4) 0.002(4) O2A 0.110(5) 0.032(3) 0.077(4) 0.013(3) 0.032(3) 0.006(3) C3A 0.046(5) 0.026(4) 0.057(5) -0.005(4) 0.011(4) 0.001(4) C4A 0.058(5) 0.035(5) 0.045(5) -0.012(4) 0.007(4) -0.001(4) O4A 0.079(4) 0.026(3) 0.068(3) -0.009(3) 0.004(3) 0.007(3) N5A 0.057(4) 0.024(4) 0.048(4) 0.001(3) -0.004(4) -0.002(3) C6A 0.064(6) 0.023(4) 0.063(5) 0.004(4) 0.000(5) 0.002(4) C7A 0.073(6) 0.037(5) 0.068(6) 0.005(4) 0.013(5) -0.001(4) C8A 0.067(5) 0.061(6) 0.047(5) -0.011(4) 0.012(4) -0.003(5) C9A 0.066(6) 0.042(5) 0.053(5) -0.004(4) 0.014(4) -0.011(4) C10A 0.049(5) 0.029(5) 0.048(5) 0.003(4) 0.000(4) 0.000(4) O1B 0.064(3) 0.032(3) 0.052(3) -0.001(2) 0.015(3) -0.004(2) C1B 0.110(7) 0.038(5) 0.085(6) -0.001(5) 0.043(6) 0.000(5) C2B 0.047(5) 0.033(4) 0.043(5) 0.006(4) 0.007(4) -0.001(4) O2B 0.071(4) 0.031(3) 0.062(3) 0.006(3) 0.010(3) -0.004(3) C3B 0.054(5) 0.031(4) 0.052(5) 0.004(4) 0.004(4) -0.003(4) C4B 0.071(6) 0.037(5) 0.053(5) 0.002(4) 0.024(4) 0.005(4) O4B 0.113(5) 0.025(3) 0.075(4) -0.008(3) 0.030(3) -0.007(3) N5B 0.055(4) 0.026(4) 0.041(4) -0.002(3) 0.007(3) 0.004(3) C6B 0.059(5) 0.032(5) 0.070(6) 0.006(5) 0.005(5) -0.005(4) C7B 0.057(5) 0.037(5) 0.066(6) 0.005(4) 0.012(5) 0.004(4) C8B 0.062(5) 0.048(5) 0.047(5) 0.000(4) 0.006(4) 0.005(4) C9B 0.066(6) 0.030(4) 0.052(5) 0.003(4) 0.006(4) -0.003(4) C10B 0.041(4) 0.038(5) 0.055(6) -0.003(4) 0.001(4) -0.001(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 O1A C10A 1.329(7) . ? O1A C2A 1.434(7) . ? C1A C3A 1.490(8) . ? C1A H1A 0.9600 . ? C1A H1B 0.9600 . ? C1A H1C 0.9600 . ? C2A O2A 1.205(8) . ? C2A C3A 1.407(8) . ? C3A C4A 1.385(8) . ? C4A O4A 1.229(7) . ? C4A N5A 1.487(8) . ? N5A C10A 1.347(7) . ? N5A C6A 1.355(8) . ? C6A C7A 1.344(9) . ? C6A H6A 0.9300 . ? C7A C8A 1.388(9) . ? C7A H7A 0.9300 . ? C8A C9A 1.369(9) . ? C8A H8A 0.9300 . ? C9A C10A 1.375(8) . ? C9A H9A 0.9300 . ? O1B C10B 1.326(7) . ? O1B C2B 1.424(7) . ? C1B C3B 1.492(8) . ? C1B H1D 0.9600 . ? C1B H1E 0.9600 . ? C1B H1F 0.9600 . ? C2B O2B 1.209(7) . ? C2B C3B 1.410(8) . ? C3B C4B 1.385(8) . ? C4B O4B 1.205(7) . ? C4B N5B 1.490(8) . ? N5B C10B 1.352(8) . ? N5B C6B 1.371(8) . ? C6B C7B 1.346(8) . ? C6B H6B 0.9300 . ? C7B C8B 1.402(9) . ? C7B H7B 0.9300 . ? C8B C9B 1.372(8) . ? C8B H8B 0.9300 . ? C9B C10B 1.375(8) . ? C9B H9B 0.9300 . ? 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 C10A O1A C2A 122.7(5) . . ? C3A C1A H1A 109.5 . . ? C3A C1A H1B 109.5 . . ? H1A C1A H1B 109.5 . . ? C3A C1A H1C 109.5 . . ? H1A C1A H1C 109.5 . . ? H1B C1A H1C 109.5 . . ? O2A C2A C3A 128.9(7) . . ? O2A C2A O1A 113.9(6) . . ? C3A C2A O1A 117.2(6) . . ? C4A C3A C2A 122.4(7) . . ? C4A C3A C1A 120.1(6) . . ? C2A C3A C1A 117.5(6) . . ? O4A C4A C3A 129.1(7) . . ? O4A C4A N5A 115.6(6) . . ? C3A C4A N5A 115.3(6) . . ? C10A N5A C6A 119.6(7) . . ? C10A N5A C4A 122.1(6) . . ? C6A N5A C4A 118.2(6) . . ? C7A C6A N5A 120.7(7) . . ? C7A C6A H6A 119.7 . . ? N5A C6A H6A 119.7 . . ? C6A C7A C8A 120.6(7) . . ? C6A C7A H7A 119.7 . . ? C8A C7A H7A 119.7 . . ? C9A C8A C7A 118.6(7) . . ? C9A C8A H8A 120.7 . . ? C7A C8A H8A 120.7 . . ? C8A C9A C10A 119.3(7) . . ? C8A C9A H9A 120.3 . . ? C10A C9A H9A 120.3 . . ? O1A C10A N5A 120.2(6) . . ? O1A C10A C9A 118.7(7) . . ? N5A C10A C9A 121.2(7) . . ? C10B O1B C2B 122.4(5) . . ? C3B C1B H1D 109.5 . . ? C3B C1B H1E 109.5 . . ? H1D C1B H1E 109.5 . . ? C3B C1B H1F 109.5 . . ? H1D C1B H1F 109.5 . . ? H1E C1B H1F 109.5 . . ? O2B C2B C3B 129.3(7) . . ? O2B C2B O1B 113.6(6) . . ? C3B C2B O1B 117.1(6) . . ? C4B C3B C2B 123.2(7) . . ? C4B C3B C1B 120.3(6) . . ? C2B C3B C1B 116.5(6) . . ? O4B C4B C3B 129.4(7) . . ? O4B C4B N5B 116.0(7) . . ? C3B C4B N5B 114.5(6) . . ? C10B N5B C6B 119.6(6) . . ? C10B N5B C4B 121.9(6) . . ? C6B N5B C4B 118.5(6) . . ? C7B C6B N5B 121.0(7) . . ? C7B C6B H6B 119.5 . . ? N5B C6B H6B 119.5 . . ? C6B C7B C8B 120.0(7) . . ? C6B C7B H7B 120.0 . . ? C8B C7B H7B 120.0 . . ? C9B C8B C7B 118.6(7) . . ? C9B C8B H8B 120.7 . . ? C7B C8B H8B 120.7 . . ? C8B C9B C10B 120.1(7) . . ? C8B C9B H9B 120.0 . . ? C10B C9B H9B 120.0 . . ? O1B C10B N5B 120.8(6) . . ? O1B C10B C9B 118.5(7) . . ? N5B C10B C9B 120.8(7) . . ? 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 C6A H6A O4A 0.93 2.33 2.660(9) 100.1 . C6B H6B O4B 0.93 2.36 2.676(10) 99.3 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.250 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.059 #===END # Compound 5b data_bw1056 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H9 N O3' _chemical_formula_weight 239.22 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 'P 2 1 /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 7.318(2) _cell_length_b 11.9840(10) _cell_length_c 12.378(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.710(10) _cell_angle_gamma 90.00 _cell_volume 1085.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type '\y-scans' _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Enraf Nonius CAD4' _diffrn_measurement_method '\w 2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% ? _diffrn_reflns_number 2066 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1909 _reflns_number_gt 977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4' _computing_cell_refinement 'SET4 in CAD4' _computing_data_reduction 'XTAL3.2' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'SHELXL-97' _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 w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.0000P] 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 1909 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2263(2) 0.12023(13) 0.38601(13) 0.0530(5) Uani 1 d . . . C2 C 0.2147(4) 0.1008(2) 0.5002(2) 0.0492(7) Uani 1 d . . . O2 O 0.2636(3) 0.00858(16) 0.52583(15) 0.0788(7) Uani 1 d . . . C3 C 0.1478(3) 0.18920(19) 0.56358(18) 0.0405(6) Uani 1 d . . . C4 C 0.0864(3) 0.2877(2) 0.51726(19) 0.0431(6) Uani 1 d . . . O4 O 0.0164(3) 0.36911(14) 0.56046(14) 0.0610(6) Uani 1 d . . . N5 N 0.1073(3) 0.29771(15) 0.39829(14) 0.0399(5) Uani 1 d . . . C6 C 0.0531(3) 0.3948(2) 0.3497(2) 0.0461(7) Uani 1 d . . . H6 H 0.0041 0.4519 0.3913 0.055 Uiso 1 calc R . . C7 C 0.0699(4) 0.4089(2) 0.2421(2) 0.0527(7) Uani 1 d . . . H7 H 0.0312 0.4747 0.2093 0.063 Uiso 1 calc R . . C8 C 0.1454(4) 0.3241(2) 0.1809(2) 0.0571(8) Uani 1 d . . . H8 H 0.1600 0.3337 0.1069 0.069 Uiso 1 calc R . . C9 C 0.1981(4) 0.2266(2) 0.2287(2) 0.0536(7) Uani 1 d . . . H9 H 0.2475 0.1691 0.1880 0.064 Uiso 1 calc R . . C10 C 0.1770(3) 0.2149(2) 0.33853(19) 0.0426(6) Uani 1 d . . . C11 C 0.1343(3) 0.17510(18) 0.68230(18) 0.0396(6) Uani 1 d . . . C12 C 0.1713(3) 0.2637(2) 0.75212(19) 0.0460(7) Uani 1 d . . . H12 H 0.2092 0.3316 0.7236 0.055 Uiso 1 calc R . . C13 C 0.1530(4) 0.2533(2) 0.8624(2) 0.0561(7) Uani 1 d . . . H13 H 0.1774 0.3140 0.9072 0.067 Uiso 1 calc R . . C14 C 0.0989(4) 0.1538(3) 0.9060(2) 0.0645(8) Uani 1 d . . . H14 H 0.0858 0.1466 0.9803 0.077 Uiso 1 calc R . . C15 C 0.0639(4) 0.0646(2) 0.8389(2) 0.0638(8) Uani 1 d . . . H15 H 0.0281 -0.0033 0.8682 0.077 Uiso 1 calc R . . C16 C 0.0816(4) 0.0750(2) 0.7284(2) 0.0520(7) Uani 1 d . . . H16 H 0.0577 0.0138 0.6843 0.062 Uiso 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 O1 0.0700(13) 0.0406(11) 0.0485(11) -0.0080(8) 0.0049(9) 0.0091(9) C2 0.0594(18) 0.0352(15) 0.0530(17) -0.0055(12) -0.0009(13) 0.0054(13) O2 0.125(2) 0.0436(11) 0.0681(14) -0.0020(10) -0.0017(12) 0.0323(12) C3 0.0457(15) 0.0320(13) 0.0439(14) -0.0028(11) -0.0010(11) 0.0005(12) C4 0.0532(16) 0.0361(14) 0.0399(14) -0.0042(11) 0.0041(12) -0.0016(12) O4 0.0977(16) 0.0393(11) 0.0464(10) -0.0011(8) 0.0141(10) 0.0185(10) N5 0.0428(12) 0.0348(11) 0.0422(12) -0.0033(9) 0.0050(9) -0.0004(10) C6 0.0529(17) 0.0355(14) 0.0499(16) 0.0028(12) 0.0027(12) 0.0011(12) C7 0.0565(18) 0.0505(17) 0.0513(17) 0.0102(13) 0.0023(13) -0.0067(14) C8 0.0597(19) 0.069(2) 0.0426(16) -0.0024(14) 0.0092(13) -0.0116(16) C9 0.0558(18) 0.0601(19) 0.0452(16) -0.0134(14) 0.0085(12) -0.0031(15) C10 0.0425(15) 0.0382(15) 0.0472(15) -0.0063(12) 0.0030(12) -0.0041(12) C11 0.0381(15) 0.0341(14) 0.0466(15) 0.0004(11) -0.0031(11) 0.0021(11) C12 0.0492(16) 0.0375(14) 0.0513(16) 0.0003(12) -0.0004(12) 0.0000(13) C13 0.0642(19) 0.0569(18) 0.0470(17) -0.0064(14) -0.0043(13) 0.0002(15) C14 0.072(2) 0.074(2) 0.0472(17) 0.0075(15) 0.0006(15) -0.0033(17) C15 0.070(2) 0.0534(18) 0.067(2) 0.0169(15) -0.0013(15) -0.0107(15) C16 0.0581(18) 0.0421(16) 0.0555(18) -0.0002(12) -0.0065(13) -0.0081(14) _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 C10 1.326(3) . ? O1 C2 1.436(3) . ? C2 O2 1.203(3) . ? C2 C3 1.410(3) . ? C3 C4 1.385(3) . ? C3 C11 1.484(3) . ? C4 O4 1.228(3) . ? C4 N5 1.487(3) . ? N5 C10 1.342(3) . ? N5 C6 1.367(3) . ? C6 C7 1.350(3) . ? C6 H6 0.9300 . ? C7 C8 1.386(4) . ? C7 H7 0.9300 . ? C8 C9 1.363(3) . ? C8 H8 0.9300 . ? C9 C10 1.377(3) . ? C9 H9 0.9300 . ? C11 C16 1.385(3) . ? C11 C12 1.394(3) . ? C12 C13 1.379(3) . ? C12 H12 0.9300 . ? C13 C14 1.369(4) . ? C13 H13 0.9300 . ? C14 C15 1.376(4) . ? C14 H14 0.9300 . ? C15 C16 1.381(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 C10 O1 C2 123.79(18) . . ? O2 C2 C3 130.3(3) . . ? O2 C2 O1 112.8(2) . . ? C3 C2 O1 116.8(2) . . ? C4 C3 C2 121.5(2) . . ? C4 C3 C11 118.8(2) . . ? C2 C3 C11 119.6(2) . . ? O4 C4 C3 129.2(2) . . ? O4 C4 N5 114.6(2) . . ? C3 C4 N5 116.2(2) . . ? C10 N5 C6 119.8(2) . . ? C10 N5 C4 122.05(19) . . ? C6 N5 C4 118.13(19) . . ? C7 C6 N5 120.7(2) . . ? C7 C6 H6 119.6 . . ? N5 C6 H6 119.6 . . ? C6 C7 C8 119.3(3) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 118.8(3) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? O1 C10 N5 119.4(2) . . ? O1 C10 C9 119.5(2) . . ? N5 C10 C9 121.1(2) . . ? C16 C11 C12 117.2(2) . . ? C16 C11 C3 121.9(2) . . ? C12 C11 C3 120.8(2) . . ? C13 C12 C11 121.7(2) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C14 C13 C12 120.0(3) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 119.4(3) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 120.6(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 121.1(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? 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 C10 O1 C2 O2 178.8(2) . . . . ? C10 O1 C2 C3 -0.5(4) . . . . ? O2 C2 C3 C4 -175.6(3) . . . . ? O1 C2 C3 C4 3.6(4) . . . . ? O2 C2 C3 C11 1.5(5) . . . . ? O1 C2 C3 C11 -179.3(2) . . . . ? C2 C3 C4 O4 175.9(3) . . . . ? C11 C3 C4 O4 -1.3(4) . . . . ? C2 C3 C4 N5 -4.2(3) . . . . ? C11 C3 C4 N5 178.7(2) . . . . ? O4 C4 N5 C10 -178.2(2) . . . . ? C3 C4 N5 C10 1.8(3) . . . . ? O4 C4 N5 C6 1.8(3) . . . . ? C3 C4 N5 C6 -178.2(2) . . . . ? C10 N5 C6 C7 -0.4(4) . . . . ? C4 N5 C6 C7 179.6(2) . . . . ? N5 C6 C7 C8 -0.9(4) . . . . ? C6 C7 C8 C9 1.5(4) . . . . ? C7 C8 C9 C10 -0.8(4) . . . . ? C2 O1 C10 N5 -1.8(3) . . . . ? C2 O1 C10 C9 178.2(2) . . . . ? C6 N5 C10 O1 -178.8(2) . . . . ? C4 N5 C10 O1 1.2(3) . . . . ? C6 N5 C10 C9 1.2(4) . . . . ? C4 N5 C10 C9 -178.9(2) . . . . ? C8 C9 C10 O1 179.4(2) . . . . ? C8 C9 C10 N5 -0.6(4) . . . . ? C4 C3 C11 C16 139.2(3) . . . . ? C2 C3 C11 C16 -37.9(4) . . . . ? C4 C3 C11 C12 -39.5(3) . . . . ? C2 C3 C11 C12 143.3(2) . . . . ? C16 C11 C12 C13 -1.2(4) . . . . ? C3 C11 C12 C13 177.6(2) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C12 C13 C14 C15 0.3(4) . . . . ? C13 C14 C15 C16 -0.5(5) . . . . ? C14 C15 C16 C11 -0.1(4) . . . . ? C12 C11 C16 C15 1.0(4) . . . . ? C3 C11 C16 C15 -177.8(2) . . . . ? 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 C6 H6 O4 0.93 2.32 2.644(3) 100.0 . C6 H6 O4 0.93 2.23 3.084(3) 151.9 3_566 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.147 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.037 #===END # Compound 11b data_1618cw1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 N2 O2' _chemical_formula_weight 190.20 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 'P 2 1 /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 10.189(2) _cell_length_b 15.928(3) _cell_length_c 11.200(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.683(8) _cell_angle_gamma 90.00 _cell_volume 1811.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type '\y-scans' _exptl_absorpt_correction_T_min 0.888 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Enraf Nonius CAD4' _diffrn_measurement_method '\w-2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% ? _diffrn_reflns_number 3377 _diffrn_reflns_av_R_equivalents 0.1082 _diffrn_reflns_av_sigmaI/netI 0.2193 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3189 _reflns_number_gt 869 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4' _computing_cell_refinement 'SET4 in CAD4' _computing_data_reduction 'XTAL3.2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'SHELXL-97' _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 w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.0000P] 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 3189 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2868 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1680 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.0105(4) 0.7611(3) 0.7995(4) 0.0464(14) Uani 1 d . . . C2A C 0.1169(6) 0.7299(3) 0.7561(5) 0.0454(16) Uani 1 d . . . O2A O 0.1278(4) 0.6436(2) 0.7492(4) 0.0583(13) Uani 1 d . . . C3A C 0.2207(5) 0.7751(4) 0.7166(5) 0.0462(16) Uani 1 d . . . C4A C 0.2181(6) 0.8623(4) 0.7206(5) 0.0478(17) Uani 1 d . . . O4A O 0.3000(4) 0.9118(2) 0.6882(4) 0.0661(14) Uani 1 d . . . N5A N 0.1041(5) 0.8959(3) 0.7724(4) 0.0464(14) Uani 1 d . . . C6A C 0.0960(6) 0.9812(3) 0.7858(5) 0.058(2) Uani 1 d . . . H6A H 0.1639 1.0147 0.7620 0.069 Uiso 1 calc R . . C7A C -0.0072(7) 1.0177(4) 0.8321(6) 0.0622(19) Uani 1 d . . . H7A H -0.0101 1.0757 0.8403 0.075 Uiso 1 calc R . . C8A C -0.1119(6) 0.9675(4) 0.8684(5) 0.0615(19) Uani 1 d . . . H8A H -0.1840 0.9922 0.9004 0.074 Uiso 1 calc R . . C9A C -0.1050(6) 0.8830(3) 0.8557(5) 0.0565(19) Uani 1 d . . . H9A H -0.1736 0.8497 0.8787 0.068 Uiso 1 calc R . . C10A C 0.0040(6) 0.8445(3) 0.8082(5) 0.0437(16) Uani 1 d . . . C11A C 0.0211(6) 0.5961(3) 0.7800(5) 0.065(2) Uani 1 d . . . H11A H 0.0409 0.5375 0.7726 0.098 Uiso 1 calc R . . H11B H -0.0551 0.6099 0.7274 0.098 Uiso 1 calc R . . H11C H 0.0038 0.6082 0.8612 0.098 Uiso 1 calc R . . C12A C 0.3373(6) 0.7327(3) 0.6687(6) 0.070(2) Uani 1 d . . . H12A H 0.3989 0.7745 0.6466 0.104 Uiso 1 calc R . . H12B H 0.3085 0.6999 0.5996 0.104 Uiso 1 calc R . . H12C H 0.3791 0.6968 0.7292 0.104 Uiso 1 calc R . . N1B N 0.0221(5) 1.1528(3) 0.5280(4) 0.0495(14) Uani 1 d . . . C2B C -0.0148(6) 1.2324(4) 0.5455(5) 0.0450(16) Uani 1 d . . . O2B O -0.1323(4) 1.2443(2) 0.5927(4) 0.0577(13) Uani 1 d . . . C3B C 0.0533(6) 1.3033(3) 0.5229(5) 0.0490(17) Uani 1 d . . . C4B C 0.1763(6) 1.2957(3) 0.4774(5) 0.0520(18) Uani 1 d . . . O4B O 0.2536(4) 1.3520(2) 0.4503(4) 0.0694(13) Uani 1 d . . . N5B N 0.2172(4) 1.2094(3) 0.4587(4) 0.0448(13) Uani 1 d . . . C6B C 0.3370(6) 1.1964(4) 0.4135(5) 0.0562(18) Uani 1 d . . . H6B H 0.3870 1.2425 0.3937 0.067 Uiso 1 calc R . . C7B C 0.3837(6) 1.1182(4) 0.3972(6) 0.063(2) Uani 1 d . . . H7B H 0.4660 1.1104 0.3687 0.075 Uiso 1 calc R . . C8B C 0.3062(6) 1.0488(4) 0.4240(6) 0.066(2) Uani 1 d . . . H8B H 0.3365 0.9946 0.4123 0.079 Uiso 1 calc R . . C9B C 0.1875(6) 1.0611(3) 0.4667(5) 0.0524(18) Uani 1 d . . . H9B H 0.1369 1.0149 0.4846 0.063 Uiso 1 calc R . . C10B C 0.1384(6) 1.1433(3) 0.4850(5) 0.0479(17) Uani 1 d . . . C11B C -0.2060(5) 1.1727(3) 0.6173(5) 0.065(2) Uani 1 d . . . H11D H -0.2858 1.1896 0.6506 0.097 Uiso 1 calc R . . H11E H -0.1554 1.1377 0.6736 0.097 Uiso 1 calc R . . H11F H -0.2272 1.1420 0.5445 0.097 Uiso 1 calc R . . C12B C 0.0036(7) 1.3905(3) 0.5475(6) 0.075(2) Uani 1 d . . . H12D H 0.0670 1.4313 0.5260 0.112 Uiso 1 calc R . . H12E H -0.0094 1.3958 0.6311 0.112 Uiso 1 calc R . . H12F H -0.0785 1.3998 0.5009 0.112 Uiso 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 N1A 0.048(3) 0.033(3) 0.058(4) 0.006(2) 0.003(3) 0.000(3) C2A 0.040(4) 0.038(4) 0.057(5) -0.002(3) -0.001(4) 0.000(3) O2A 0.050(3) 0.038(2) 0.089(4) -0.003(2) 0.018(3) 0.008(2) C3A 0.040(4) 0.042(4) 0.057(5) 0.004(3) 0.007(3) 0.009(3) C4A 0.044(4) 0.049(4) 0.051(5) -0.001(3) 0.002(4) 0.007(3) O4A 0.053(3) 0.055(3) 0.092(4) 0.007(2) 0.021(3) -0.021(2) N5A 0.053(4) 0.031(3) 0.054(4) 0.001(2) 0.001(3) -0.004(3) C6A 0.063(5) 0.043(4) 0.067(5) 0.001(3) 0.001(4) -0.005(4) C7A 0.075(5) 0.040(4) 0.070(5) 0.000(4) -0.001(4) 0.005(4) C8A 0.053(5) 0.060(4) 0.072(5) -0.002(4) 0.006(4) 0.010(4) C9A 0.060(5) 0.044(4) 0.068(5) 0.004(3) 0.017(4) 0.001(3) C10A 0.049(4) 0.039(4) 0.042(4) -0.002(3) -0.001(3) -0.006(3) C11A 0.067(5) 0.042(4) 0.087(6) 0.006(4) 0.010(4) 0.006(4) C12A 0.066(5) 0.058(4) 0.086(5) 0.009(4) 0.015(4) 0.007(4) N1B 0.043(3) 0.039(3) 0.068(4) -0.007(3) 0.015(3) -0.003(3) C2B 0.044(4) 0.057(4) 0.033(4) 0.003(3) 0.000(3) 0.004(4) O2B 0.054(3) 0.047(3) 0.074(3) -0.006(2) 0.020(3) 0.007(2) C3B 0.056(4) 0.032(3) 0.059(5) 0.002(3) 0.004(4) 0.005(3) C4B 0.061(5) 0.039(4) 0.056(5) 0.009(3) 0.008(4) -0.002(4) O4B 0.069(3) 0.045(2) 0.096(4) 0.004(3) 0.017(3) -0.012(2) N5B 0.047(3) 0.039(3) 0.050(4) 0.002(3) 0.009(3) -0.001(3) C6B 0.044(4) 0.056(4) 0.069(5) 0.009(4) 0.007(4) -0.013(4) C7B 0.056(5) 0.059(4) 0.075(5) -0.007(4) 0.018(4) -0.002(4) C8B 0.064(5) 0.047(4) 0.089(6) -0.009(4) 0.024(4) 0.006(4) C9B 0.047(4) 0.037(4) 0.073(5) 0.004(3) 0.005(4) -0.003(3) C10B 0.051(4) 0.037(3) 0.056(5) 0.008(3) 0.009(4) 0.001(3) C11B 0.049(4) 0.059(4) 0.089(6) 0.010(4) 0.018(4) 0.003(3) C12B 0.093(6) 0.042(4) 0.090(6) -0.006(4) 0.009(5) 0.007(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 N1A C2A 1.321(6) . ? N1A C10A 1.335(6) . ? C2A O2A 1.381(6) . ? C2A C3A 1.382(7) . ? O2A C11A 1.391(6) . ? C3A C4A 1.389(7) . ? C3A C12A 1.504(6) . ? C4A O4A 1.224(6) . ? C4A N5A 1.444(6) . ? N5A C6A 1.369(6) . ? N5A C10A 1.392(6) . ? C6A C7A 1.342(7) . ? C6A H6A 0.9300 . ? C7A C8A 1.419(7) . ? C7A H7A 0.9300 . ? C8A C9A 1.356(7) . ? C8A H8A 0.9300 . ? C9A C10A 1.410(7) . ? C9A H9A 0.9300 . ? C11A H11A 0.9600 . ? C11A H11B 0.9600 . ? C11A H11C 0.9600 . ? C12A H12A 0.9600 . ? C12A H12B 0.9600 . ? C12A H12C 0.9600 . ? N1B C10B 1.324(6) . ? N1B C2B 1.341(6) . ? C2B O2B 1.361(6) . ? C2B C3B 1.361(7) . ? O2B C11B 1.405(5) . ? C3B C4B 1.396(7) . ? C3B C12B 1.511(6) . ? C4B O4B 1.247(6) . ? C4B N5B 1.457(6) . ? N5B C10B 1.370(6) . ? N5B C6B 1.375(6) . ? C6B C7B 1.352(7) . ? C6B H6B 0.9300 . ? C7B C8B 1.405(7) . ? C7B H7B 0.9300 . ? C8B C9B 1.351(7) . ? C8B H8B 0.9300 . ? C9B C10B 1.422(7) . ? C9B H9B 0.9300 . ? C11B H11D 0.9600 . ? C11B H11E 0.9600 . ? C11B H11F 0.9600 . ? C12B H12D 0.9600 . ? C12B H12E 0.9600 . ? C12B H12F 0.9600 . ? 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 C2A N1A C10A 116.7(5) . . ? N1A C2A O2A 117.8(5) . . ? N1A C2A C3A 126.4(5) . . ? O2A C2A C3A 115.7(5) . . ? C2A O2A C11A 117.3(4) . . ? C2A C3A C4A 119.6(5) . . ? C2A C3A C12A 121.9(5) . . ? C4A C3A C12A 118.5(5) . . ? O4A C4A C3A 128.2(6) . . ? O4A C4A N5A 118.1(5) . . ? C3A C4A N5A 113.7(5) . . ? C6A N5A C10A 120.0(5) . . ? C6A N5A C4A 118.0(5) . . ? C10A N5A C4A 122.0(4) . . ? C7A C6A N5A 121.9(5) . . ? C7A C6A H6A 119.1 . . ? N5A C6A H6A 119.1 . . ? C6A C7A C8A 119.8(5) . . ? C6A C7A H7A 120.1 . . ? C8A C7A H7A 120.1 . . ? C9A C8A C7A 118.8(6) . . ? C9A C8A H8A 120.6 . . ? C7A C8A H8A 120.6 . . ? C8A C9A C10A 121.3(6) . . ? C8A C9A H9A 119.3 . . ? C10A C9A H9A 119.3 . . ? N1A C10A N5A 121.5(5) . . ? N1A C10A C9A 120.4(5) . . ? N5A C10A C9A 118.1(5) . . ? O2A C11A H11A 109.5 . . ? O2A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? O2A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C3A C12A H12A 109.5 . . ? C3A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C3A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C10B N1B C2B 115.5(5) . . ? N1B C2B O2B 117.0(5) . . ? N1B C2B C3B 127.2(5) . . ? O2B C2B C3B 115.8(5) . . ? C2B O2B C11B 117.7(4) . . ? C2B C3B C4B 118.8(5) . . ? C2B C3B C12B 123.1(5) . . ? C4B C3B C12B 118.1(5) . . ? O4B C4B C3B 129.0(5) . . ? O4B C4B N5B 116.7(5) . . ? C3B C4B N5B 114.3(5) . . ? C10B N5B C6B 121.2(5) . . ? C10B N5B C4B 120.9(5) . . ? C6B N5B C4B 117.9(5) . . ? C7B C6B N5B 121.4(5) . . ? C7B C6B H6B 119.3 . . ? N5B C6B H6B 119.3 . . ? C6B C7B C8B 119.1(6) . . ? C6B C7B H7B 120.5 . . ? C8B C7B H7B 120.5 . . ? C9B C8B C7B 119.8(5) . . ? C9B C8B H8B 120.1 . . ? C7B C8B H8B 120.1 . . ? C8B C9B C10B 121.3(5) . . ? C8B C9B H9B 119.3 . . ? C10B C9B H9B 119.3 . . ? N1B C10B N5B 123.3(5) . . ? N1B C10B C9B 119.5(5) . . ? N5B C10B C9B 117.2(5) . . ? O2B C11B H11D 109.5 . . ? O2B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? O2B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C3B C12B H12D 109.5 . . ? C3B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C3B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? 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 C6A H6A O4A 0.93 2.34 2.666(7) 100.0 . C6B H6B O4B 0.93 2.33 2.662(7) 100.5 . _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.192 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.050 #===END # Compound 11c data_1617ha1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N4 O' _chemical_formula_weight 238.25 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 'P 2 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 10.868(3) _cell_length_b 8.7030(10) _cell_length_c 11.834(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.670(10) _cell_angle_gamma 90.00 _cell_volume 1100.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type '\y-scans' _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Enraf Nonius CAD4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% ? _diffrn_reflns_number 2036 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1929 _reflns_number_gt 1432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4' _computing_cell_refinement 'SET4 in CAD4' _computing_data_reduction 'XTAL3.2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON' _computing_publication_material 'SHELXL-97' _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 w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.1856P] 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 SHELXL _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1929 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.30538(13) -0.17127(16) 1.10261(11) 0.0401(4) Uani 1 d . . . C2 C 0.25622(14) -0.25903(18) 1.00981(13) 0.0352(4) Uani 1 d . . . N2 N 0.22536(13) -0.40258(15) 1.04308(11) 0.0413(4) Uani 1 d . . . H2 H 0.2376 -0.4174 1.1200 0.050 Uiso 1 d R . . C3 C 0.24198(16) -0.2070(2) 0.89811(14) 0.0409(4) Uani 1 d . . . H3 H 0.2069 -0.2714 0.8380 0.049 Uiso 1 calc R . . C4 C 0.27933(15) -0.0596(2) 0.87403(13) 0.0390(4) Uani 1 d . . . O4 O 0.27349(13) 0.00203(14) 0.77898(10) 0.0530(4) Uani 1 d . . . N5 N 0.33369(12) 0.02941(15) 0.97399(11) 0.0358(3) Uani 1 d . . . C6 C 0.37717(16) 0.1746(2) 0.95670(16) 0.0433(4) Uani 1 d . . . H6 H 0.3684 0.2130 0.8823 0.052 Uiso 1 calc R . . C7 C 0.43193(17) 0.2614(2) 1.04556(16) 0.0487(5) Uani 1 d . . . H7 H 0.4619 0.3587 1.0327 0.058 Uiso 1 calc R . . C8 C 0.44368(18) 0.2044(2) 1.15827(16) 0.0510(5) Uani 1 d . . . H8 H 0.4827 0.2633 1.2202 0.061 Uiso 1 calc R . . C9 C 0.39820(18) 0.0643(2) 1.17618(15) 0.0477(5) Uani 1 d . . . H9 H 0.4030 0.0291 1.2511 0.057 Uiso 1 calc R . . C10 C 0.34310(15) -0.03076(19) 1.08310(13) 0.0365(4) Uani 1 d . . . C11 C 0.16285(15) -0.52278(18) 0.97963(13) 0.0376(4) Uani 1 d . . . C12 C 0.12456(16) -0.6463(2) 1.03895(15) 0.0436(4) Uani 1 d . . . H12 H 0.1407 -0.6482 1.1189 0.052 Uiso 1 calc R . . C13 C 0.06259(17) -0.7651(2) 0.97740(17) 0.0505(5) Uani 1 d . . . H13 H 0.0362 -0.8491 1.0152 0.061 Uiso 1 calc R . . C14 C 0.03968(19) -0.7594(2) 0.85945(18) 0.0582(6) Uani 1 d . . . H14 H -0.0026 -0.8384 0.8157 0.070 Uiso 1 calc R . . C15 C 0.0808(2) -0.6348(2) 0.80916(17) 0.0664(6) Uani 1 d . . . H15 H 0.0652 -0.6312 0.7292 0.080 Uiso 1 calc R . . N3 N 0.14213(17) -0.51616(17) 0.86565(12) 0.0567(5) Uani 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 N1 0.0508(9) 0.0384(8) 0.0301(7) -0.0010(6) 0.0046(6) 0.0007(6) C2 0.0391(9) 0.0348(9) 0.0310(8) -0.0010(7) 0.0040(7) 0.0042(7) N2 0.0567(9) 0.0371(8) 0.0281(7) 0.0004(6) 0.0029(6) -0.0020(7) C3 0.0491(10) 0.0411(10) 0.0301(9) -0.0022(7) 0.0009(7) 0.0018(8) C4 0.0448(10) 0.0409(9) 0.0302(9) 0.0011(7) 0.0041(7) 0.0077(8) O4 0.0788(10) 0.0459(7) 0.0328(7) 0.0061(5) 0.0067(6) 0.0036(7) N5 0.0390(8) 0.0341(8) 0.0341(7) 0.0000(6) 0.0065(6) 0.0058(6) C6 0.0472(10) 0.0391(9) 0.0456(10) 0.0051(8) 0.0135(8) 0.0052(8) C7 0.0506(11) 0.0364(10) 0.0612(12) -0.0031(9) 0.0155(9) -0.0032(8) C8 0.0564(12) 0.0463(11) 0.0493(11) -0.0151(9) 0.0066(9) -0.0034(9) C9 0.0602(12) 0.0468(10) 0.0346(9) -0.0046(8) 0.0048(8) 0.0014(9) C10 0.0406(9) 0.0360(9) 0.0331(9) -0.0007(7) 0.0071(7) 0.0063(7) C11 0.0408(9) 0.0346(9) 0.0359(9) -0.0042(7) 0.0032(7) 0.0065(7) C12 0.0447(10) 0.0485(11) 0.0374(9) -0.0019(8) 0.0071(7) -0.0019(8) C13 0.0505(11) 0.0460(11) 0.0546(11) -0.0045(9) 0.0086(9) -0.0079(9) C14 0.0643(13) 0.0449(11) 0.0584(13) -0.0150(9) -0.0073(10) 0.0011(9) C15 0.1066(18) 0.0471(12) 0.0377(11) -0.0092(9) -0.0067(11) 0.0049(12) N3 0.0924(13) 0.0395(9) 0.0351(8) -0.0023(7) 0.0036(8) -0.0007(8) _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 N1 C10 1.324(2) . ? N1 C2 1.363(2) . ? C2 N2 1.370(2) . ? C2 C3 1.379(2) . ? N2 C11 1.390(2) . ? N2 H2 0.9048 . ? C3 C4 1.391(2) . ? C3 H3 0.9300 . ? C4 O4 1.2373(19) . ? C4 N5 1.446(2) . ? N5 C6 1.377(2) . ? N5 C10 1.380(2) . ? C6 C7 1.342(2) . ? C6 H6 0.9300 . ? C7 C8 1.406(3) . ? C7 H7 0.9300 . ? C8 C9 1.348(3) . ? C8 H8 0.9300 . ? C9 C10 1.418(2) . ? C9 H9 0.9300 . ? C11 N3 1.327(2) . ? C11 C12 1.389(2) . ? C12 C13 1.368(2) . ? C12 H12 0.9300 . ? C13 C14 1.373(3) . ? C13 H13 0.9300 . ? C14 C15 1.352(3) . ? C14 H14 0.9300 . ? C15 N3 1.339(2) . ? C15 H15 0.9300 . ? 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 C10 N1 C2 117.71(14) . . ? N1 C2 N2 111.09(13) . . ? N1 C2 C3 123.12(15) . . ? N2 C2 C3 125.79(15) . . ? C2 N2 C11 130.72(14) . . ? C2 N2 H2 114.9 . . ? C11 N2 H2 113.8 . . ? C2 C3 C4 120.93(15) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? O4 C4 C3 128.21(15) . . ? O4 C4 N5 117.12(15) . . ? C3 C4 N5 114.66(14) . . ? C6 N5 C10 121.28(14) . . ? C6 N5 C4 118.00(14) . . ? C10 N5 C4 120.71(14) . . ? C7 C6 N5 120.99(16) . . ? C7 C6 H6 119.5 . . ? N5 C6 H6 119.5 . . ? C6 C7 C8 119.60(17) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 119.79(17) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 121.34(17) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? N1 C10 N5 122.84(14) . . ? N1 C10 C9 120.21(15) . . ? N5 C10 C9 116.94(15) . . ? N3 C11 C12 122.48(15) . . ? N3 C11 N2 119.38(15) . . ? C12 C11 N2 118.15(15) . . ? C13 C12 C11 118.67(17) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C14 119.54(19) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 117.65(18) . . ? C15 C14 H14 121.2 . . ? C13 C14 H14 121.2 . . ? N3 C15 C14 124.98(19) . . ? N3 C15 H15 117.5 . . ? C14 C15 H15 117.5 . . ? C11 N3 C15 116.69(17) . . ? 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 C6 H6 O4 0.93 2.34 2.659(2) 99.8 . N2 H2 O4 0.90 1.99 2.877(2) 166.0 4_556 C3 H3 N3 0.93 2.29 2.900(2) 123.1 . _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.277 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.041 #===END