# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Jacob Schwarz' _publ_contact_author_email SCHWARZ.JACOB@GENE.COM _publ_section_title ; Robust Preparation of Novel Imidazo[5,1-b][1,3,4]oxadiazoles ; _publ_contact_letter ; Structure shows A level alerts due to percent data coverage of data. This is a function of crystal symmetry, the data collection strategy and the time alloted to collect this structure on our machine. ; loop_ _publ_author_name 'Jacob Schwarz' 'Tuan P. Tran' 'Nandini Patel' 'Brian Samas' # Attachment 'I801_1a_v2.cif' data_i801 _database_code_depnum_ccdc_archive 'CCDC 743852' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H11 N3 O' _chemical_formula_weight 261.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 5.6393(2) _cell_length_b 11.9631(4) _cell_length_c 38.0483(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2566.87(15) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4330 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description plate _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.707 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8654 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 59.18 _reflns_number_total 3574 _reflns_number_gt 3105 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.0284P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(3) _refine_ls_number_reflns 3574 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.3631(5) 0.7576(2) 0.20059(7) 0.0676(7) Uani 1 1 d . . . H1 H 1.2843 0.7400 0.1798 0.081 Uiso 1 1 calc R . . C2 C 1.5603(5) 0.6964(2) 0.21028(8) 0.0761(8) Uani 1 1 d . . . H2 H 1.6133 0.6386 0.1959 0.091 Uiso 1 1 calc R . . C3 C 1.6795(5) 0.7202(3) 0.24110(8) 0.0798(9) Uani 1 1 d . . . H3 H 1.8115 0.6787 0.2478 0.096 Uiso 1 1 calc R . . C4 C 1.5985(6) 0.8065(3) 0.26161(8) 0.0852(9) Uani 1 1 d . . . H4 H 1.6775 0.8235 0.2824 0.102 Uiso 1 1 calc R . . C5 C 1.4036(6) 0.8683(3) 0.25212(7) 0.0762(8) Uani 1 1 d . . . H5 H 1.3534 0.9266 0.2665 0.091 Uiso 1 1 calc R . . C6 C 1.2804(5) 0.8448(2) 0.22134(6) 0.0602(7) Uani 1 1 d . . . C7 C 1.0780(5) 0.9114(2) 0.21130(6) 0.0586(6) Uani 1 1 d . . . C8 C 0.7882(5) 1.0350(2) 0.21062(7) 0.0734(8) Uani 1 1 d . . . H8 H 0.6899 1.0938 0.2172 0.088 Uiso 1 1 calc R . . C9 C 0.7675(5) 0.9723(2) 0.18122(7) 0.0610(6) Uani 1 1 d . . . C10 C 0.7497(5) 0.8651(2) 0.13567(7) 0.0620(7) Uani 1 1 d . . . C11 C 0.6529(5) 0.8216(2) 0.10284(6) 0.0629(7) Uani 1 1 d . . . C12 C 0.4490(5) 0.8640(2) 0.08808(8) 0.0776(8) Uani 1 1 d . . . H12 H 0.3655 0.9205 0.0994 0.093 Uiso 1 1 calc R . . C13 C 0.3685(6) 0.8225(3) 0.05639(8) 0.0898(9) Uani 1 1 d . . . H13 H 0.2320 0.8518 0.0462 0.108 Uiso 1 1 calc R . . C14 C 0.4887(6) 0.7385(3) 0.03993(8) 0.0870(9) Uani 1 1 d . . . H14 H 0.4343 0.7109 0.0185 0.104 Uiso 1 1 calc R . . C15 C 0.6885(6) 0.6948(3) 0.05473(8) 0.0861(9) Uani 1 1 d . . . H15 H 0.7681 0.6368 0.0435 0.103 Uiso 1 1 calc R . . C16 C 0.7731(6) 0.7354(2) 0.08597(7) 0.0763(8) Uani 1 1 d . . . H16 H 0.9100 0.7055 0.0958 0.092 Uiso 1 1 calc R . . C17 C 0.2897(5) 0.1610(2) 0.03560(6) 0.0724(8) Uani 1 1 d . . . H17 H 0.4281 0.2010 0.0400 0.087 Uiso 1 1 calc R . . C18 C 0.2249(7) 0.1375(3) 0.00144(7) 0.0893(9) Uani 1 1 d . . . H18 H 0.3184 0.1629 -0.0170 0.107 Uiso 1 1 calc R . . C19 C 0.0243(7) 0.0772(3) -0.00546(8) 0.0914(10) Uani 1 1 d . . . H19 H -0.0162 0.0596 -0.0285 0.110 Uiso 1 1 calc R . . C20 C -0.1173(6) 0.0427(2) 0.02196(9) 0.0874(9) Uani 1 1 d . . . H20 H -0.2557 0.0031 0.0174 0.105 Uiso 1 1 calc R . . C21 C -0.0548(5) 0.0666(2) 0.05608(7) 0.0732(8) Uani 1 1 d . . . H21 H -0.1512 0.0429 0.0744 0.088 Uiso 1 1 calc R . . C22 C 0.1509(4) 0.1258(2) 0.06330(6) 0.0571(6) Uani 1 1 d . . . C23 C 0.2174(5) 0.14708(19) 0.09961(6) 0.0551(6) Uani 1 1 d . . . C24 C 0.2268(5) 0.1481(2) 0.15725(6) 0.0669(7) Uani 1 1 d . . . H24 H 0.1878 0.1339 0.1806 0.080 Uiso 1 1 calc R . . C25 C 0.4108(5) 0.2096(2) 0.14592(6) 0.0573(6) Uani 1 1 d . . . C26 C 0.6946(4) 0.31190(19) 0.12511(6) 0.0548(6) Uani 1 1 d . . . C27 C 0.8945(4) 0.38877(19) 0.12740(6) 0.0563(6) Uani 1 1 d . . . C28 C 0.9746(5) 0.4253(2) 0.15958(7) 0.0741(8) Uani 1 1 d . . . H28 H 0.9014 0.4000 0.1800 0.089 Uiso 1 1 calc R . . C29 C 1.1617(6) 0.4988(3) 0.16194(9) 0.0861(9) Uani 1 1 d . . . H29 H 1.2129 0.5237 0.1838 0.103 Uiso 1 1 calc R . . C30 C 1.2726(6) 0.5353(2) 0.13188(9) 0.0821(8) Uani 1 1 d . . . H30 H 1.3999 0.5844 0.1333 0.099 Uiso 1 1 calc R . . C31 C 1.1938(5) 0.4985(2) 0.09978(8) 0.0812(9) Uani 1 1 d . . . H31 H 1.2685 0.5234 0.0795 0.097 Uiso 1 1 calc R . . C32 C 1.0054(5) 0.4250(2) 0.09709(7) 0.0711(8) Uani 1 1 d . . . H32 H 0.9541 0.4003 0.0752 0.085 Uiso 1 1 calc R . . N1 N 0.9820(4) 0.99598(18) 0.22916(6) 0.0725(6) Uani 1 1 d . . . N2 N 0.9459(4) 0.89692(15) 0.18137(5) 0.0592(5) Uani 1 1 d . . . N3 N 0.9347(4) 0.82786(16) 0.15229(5) 0.0619(5) Uani 1 1 d . . . N4 N 0.1063(4) 0.10969(17) 0.12815(5) 0.0649(6) Uani 1 1 d . . . N5 N 0.4090(4) 0.20976(15) 0.11034(5) 0.0524(5) Uani 1 1 d . . . N6 N 0.5894(4) 0.27718(16) 0.09690(5) 0.0552(5) Uani 1 1 d . . . O1 O 0.6352(3) 0.95386(14) 0.15146(5) 0.0680(5) Uani 1 1 d . . . O2 O 0.5981(3) 0.27499(14) 0.15633(4) 0.0611(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0696(19) 0.0609(16) 0.0722(17) -0.0002(14) -0.0130(14) -0.0031(14) C2 0.079(2) 0.0663(17) 0.0834(19) 0.0042(15) -0.0043(17) -0.0031(16) C3 0.075(2) 0.083(2) 0.082(2) 0.0262(18) -0.0114(17) -0.0118(17) C4 0.099(3) 0.095(2) 0.0623(17) 0.0196(18) -0.0163(17) -0.026(2) C5 0.091(2) 0.0809(18) 0.0568(16) 0.0065(14) 0.0019(16) -0.0144(18) C6 0.0661(18) 0.0588(15) 0.0558(14) 0.0081(13) 0.0061(13) -0.0137(13) C7 0.0623(17) 0.0554(15) 0.0582(15) 0.0000(12) 0.0118(13) -0.0103(14) C8 0.073(2) 0.0623(16) 0.0843(19) -0.0039(16) 0.0244(17) 0.0004(15) C9 0.0606(17) 0.0527(14) 0.0695(17) 0.0022(14) 0.0119(14) -0.0006(13) C10 0.0597(17) 0.0549(14) 0.0713(16) 0.0078(13) 0.0088(14) 0.0042(13) C11 0.0647(19) 0.0574(15) 0.0666(16) 0.0078(13) 0.0007(13) -0.0038(13) C12 0.069(2) 0.0697(17) 0.094(2) 0.0046(16) -0.0071(16) 0.0082(15) C13 0.081(2) 0.094(2) 0.094(2) 0.003(2) -0.0259(18) 0.0014(19) C14 0.095(3) 0.089(2) 0.077(2) -0.0010(18) -0.0133(18) -0.0064(19) C15 0.092(2) 0.089(2) 0.0773(19) -0.0097(17) -0.0063(18) 0.0134(19) C16 0.0733(19) 0.0767(18) 0.0788(18) -0.0010(16) -0.0071(16) 0.0127(16) C17 0.0752(19) 0.0847(18) 0.0574(15) -0.0045(15) -0.0067(15) -0.0042(16) C18 0.100(3) 0.111(2) 0.0563(16) -0.0065(16) -0.0073(17) -0.004(2) C19 0.105(3) 0.096(2) 0.072(2) -0.0196(18) -0.0299(19) 0.012(2) C20 0.079(2) 0.081(2) 0.102(2) -0.0161(19) -0.0256(19) 0.0007(17) C21 0.0739(19) 0.0690(17) 0.0768(18) -0.0036(15) -0.0095(16) -0.0067(15) C22 0.0616(17) 0.0518(13) 0.0579(14) -0.0007(12) -0.0055(12) 0.0036(12) C23 0.0564(16) 0.0510(14) 0.0580(14) -0.0020(11) -0.0007(13) -0.0009(12) C24 0.0787(19) 0.0694(17) 0.0526(14) 0.0041(13) 0.0051(14) -0.0124(16) C25 0.0648(17) 0.0573(14) 0.0499(15) 0.0030(12) -0.0007(12) -0.0003(13) C26 0.0556(15) 0.0575(14) 0.0513(13) -0.0042(12) 0.0028(12) 0.0040(12) C27 0.0540(15) 0.0528(13) 0.0622(15) -0.0055(12) 0.0004(13) 0.0041(11) C28 0.079(2) 0.0764(18) 0.0667(18) 0.0002(15) -0.0057(15) -0.0085(16) C29 0.090(2) 0.080(2) 0.088(2) -0.0052(17) -0.0167(18) -0.0193(19) C30 0.072(2) 0.0628(17) 0.112(2) -0.0140(18) 0.0003(19) -0.0098(15) C31 0.079(2) 0.0667(17) 0.097(2) -0.0062(16) 0.0271(17) -0.0064(16) C32 0.077(2) 0.0677(17) 0.0688(17) -0.0104(14) 0.0091(14) -0.0047(15) N1 0.0784(17) 0.0669(14) 0.0720(15) -0.0040(12) 0.0200(13) -0.0130(13) N2 0.0621(14) 0.0516(12) 0.0640(13) -0.0008(10) 0.0058(11) -0.0023(10) N3 0.0667(14) 0.0550(11) 0.0642(13) -0.0017(11) 0.0026(11) 0.0031(11) N4 0.0715(14) 0.0621(13) 0.0612(12) 0.0030(11) 0.0080(12) -0.0069(11) N5 0.0581(13) 0.0525(11) 0.0465(11) 0.0026(9) 0.0015(9) -0.0006(10) N6 0.0576(13) 0.0563(11) 0.0516(11) 0.0014(10) 0.0027(10) -0.0002(10) O1 0.0639(12) 0.0602(10) 0.0799(12) 0.0012(9) 0.0065(10) 0.0075(9) O2 0.0671(11) 0.0680(10) 0.0480(9) 0.0007(8) -0.0015(8) -0.0047(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.382(4) . ? C1 C6 1.389(3) . ? C1 H1 0.9300 . ? C2 C3 1.381(4) . ? C2 H2 0.9300 . ? C3 C4 1.373(4) . ? C3 H3 0.9300 . ? C4 C5 1.373(4) . ? C4 H4 0.9300 . ? C5 C6 1.391(3) . ? C5 H5 0.9300 . ? C6 C7 1.443(4) . ? C7 N1 1.334(3) . ? C7 N2 1.371(3) . ? C8 C9 1.352(3) . ? C8 N1 1.382(4) . ? C8 H8 0.9300 . ? C9 N2 1.351(3) . ? C9 O1 1.374(3) . ? C10 N3 1.299(3) . ? C10 O1 1.380(3) . ? C10 C11 1.459(3) . ? C11 C12 1.377(4) . ? C11 C16 1.391(4) . ? C12 C13 1.381(4) . ? C12 H12 0.9300 . ? C13 C14 1.364(4) . ? C13 H13 0.9300 . ? C14 C15 1.364(4) . ? C14 H14 0.9300 . ? C15 C16 1.370(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C22 1.379(3) . ? C17 C18 1.379(3) . ? C17 H17 0.9300 . ? C18 C19 1.367(5) . ? C18 H18 0.9300 . ? C19 C20 1.377(4) . ? C19 H19 0.9300 . ? C20 C21 1.375(4) . ? C20 H20 0.9300 . ? C21 C22 1.387(4) . ? C21 H21 0.9300 . ? C22 C23 1.454(3) . ? C23 N4 1.331(3) . ? C23 N5 1.377(3) . ? C24 C25 1.344(3) . ? C24 N4 1.378(3) . ? C24 H24 0.9300 . ? C25 N5 1.354(3) . ? C25 O2 1.372(3) . ? C26 N6 1.295(3) . ? C26 O2 1.379(3) . ? C26 C27 1.457(3) . ? C27 C28 1.376(3) . ? C27 C32 1.381(3) . ? C28 C29 1.376(4) . ? C28 H28 0.9300 . ? C29 C30 1.374(4) . ? C29 H29 0.9300 . ? C30 C31 1.372(4) . ? C30 H30 0.9300 . ? C31 C32 1.383(4) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? N2 N3 1.382(3) . ? N5 N6 1.395(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.1(3) . . ? C2 C1 H1 119.4 . . ? C6 C1 H1 119.4 . . ? C3 C2 C1 120.6(3) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 118.4(3) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C4 C5 121.4(3) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 117.5(3) . . ? C1 C6 C7 122.0(2) . . ? C5 C6 C7 120.5(3) . . ? N1 C7 N2 107.4(2) . . ? N1 C7 C6 127.2(3) . . ? N2 C7 C6 125.4(2) . . ? C9 C8 N1 107.6(2) . . ? C9 C8 H8 126.2 . . ? N1 C8 H8 126.2 . . ? N2 C9 C8 107.6(2) . . ? N2 C9 O1 107.5(2) . . ? C8 C9 O1 144.9(3) . . ? N3 C10 O1 115.3(2) . . ? N3 C10 C11 126.5(2) . . ? O1 C10 C11 118.2(2) . . ? C12 C11 C16 119.4(3) . . ? C12 C11 C10 122.0(3) . . ? C16 C11 C10 118.5(3) . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.7(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 119.6(3) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? C22 C17 C18 120.5(3) . . ? C22 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 119.5(3) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C21 C20 C19 120.3(3) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 120.5(3) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C17 C22 C21 118.6(2) . . ? C17 C22 C23 121.8(2) . . ? C21 C22 C23 119.6(2) . . ? N4 C23 N5 108.1(2) . . ? N4 C23 C22 126.5(2) . . ? N5 C23 C22 125.4(2) . . ? C25 C24 N4 107.8(2) . . ? C25 C24 H24 126.1 . . ? N4 C24 H24 126.1 . . ? C24 C25 N5 108.4(2) . . ? C24 C25 O2 144.5(2) . . ? N5 C25 O2 107.1(2) . . ? N6 C26 O2 115.5(2) . . ? N6 C26 C27 127.3(2) . . ? O2 C26 C27 117.1(2) . . ? C28 C27 C32 119.6(2) . . ? C28 C27 C26 120.5(2) . . ? C32 C27 C26 119.9(2) . . ? C29 C28 C27 120.8(3) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C30 C29 C28 119.8(3) . . ? C30 C29 H29 120.1 . . ? C28 C29 H29 120.1 . . ? C31 C30 C29 119.4(3) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C30 C31 C32 121.2(3) . . ? C30 C31 H31 119.4 . . ? C32 C31 H31 119.4 . . ? C27 C32 C31 119.0(3) . . ? C27 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C7 N1 C8 108.5(2) . . ? C9 N2 C7 108.9(2) . . ? C9 N2 N3 111.2(2) . . ? C7 N2 N3 139.9(2) . . ? C10 N3 N2 102.8(2) . . ? C23 N4 C24 108.1(2) . . ? C25 N5 C23 107.6(2) . . ? C25 N5 N6 111.2(2) . . ? C23 N5 N6 141.09(19) . . ? C26 N6 N5 102.44(17) . . ? C9 O1 C10 103.2(2) . . ? C25 O2 C26 103.75(17) . . ? 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 C6 C1 C2 C3 0.4(4) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C2 C1 C6 C5 0.1(4) . . . . ? C2 C1 C6 C7 178.5(2) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C4 C5 C6 C7 -179.0(2) . . . . ? C1 C6 C7 N1 179.3(2) . . . . ? C5 C6 C7 N1 -2.3(4) . . . . ? C1 C6 C7 N2 0.6(4) . . . . ? C5 C6 C7 N2 179.0(2) . . . . ? N1 C8 C9 N2 -0.7(3) . . . . ? N1 C8 C9 O1 178.1(3) . . . . ? N3 C10 C11 C12 177.0(2) . . . . ? O1 C10 C11 C12 -2.1(4) . . . . ? N3 C10 C11 C16 -3.6(4) . . . . ? O1 C10 C11 C16 177.3(2) . . . . ? C16 C11 C12 C13 -1.5(4) . . . . ? C10 C11 C12 C13 177.9(3) . . . . ? C11 C12 C13 C14 1.0(5) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C13 C14 C15 C16 -0.9(5) . . . . ? C14 C15 C16 C11 0.4(5) . . . . ? C12 C11 C16 C15 0.8(4) . . . . ? C10 C11 C16 C15 -178.6(3) . . . . ? C22 C17 C18 C19 -1.2(5) . . . . ? C17 C18 C19 C20 1.9(5) . . . . ? C18 C19 C20 C21 -1.4(5) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? C18 C17 C22 C21 -0.1(4) . . . . ? C18 C17 C22 C23 178.5(3) . . . . ? C20 C21 C22 C17 0.6(4) . . . . ? C20 C21 C22 C23 -178.0(3) . . . . ? C17 C22 C23 N4 -174.6(3) . . . . ? C21 C22 C23 N4 4.1(4) . . . . ? C17 C22 C23 N5 5.2(4) . . . . ? C21 C22 C23 N5 -176.2(2) . . . . ? N4 C24 C25 N5 -0.5(3) . . . . ? N4 C24 C25 O2 177.3(3) . . . . ? N6 C26 C27 C28 174.5(3) . . . . ? O2 C26 C27 C28 -2.5(3) . . . . ? N6 C26 C27 C32 -5.8(4) . . . . ? O2 C26 C27 C32 177.2(2) . . . . ? C32 C27 C28 C29 1.0(4) . . . . ? C26 C27 C28 C29 -179.3(2) . . . . ? C27 C28 C29 C30 -0.9(5) . . . . ? C28 C29 C30 C31 0.5(5) . . . . ? C29 C30 C31 C32 -0.3(5) . . . . ? C28 C27 C32 C31 -0.7(4) . . . . ? C26 C27 C32 C31 179.6(2) . . . . ? C30 C31 C32 C27 0.3(4) . . . . ? N2 C7 N1 C8 0.2(3) . . . . ? C6 C7 N1 C8 -178.7(2) . . . . ? C9 C8 N1 C7 0.3(3) . . . . ? C8 C9 N2 C7 0.8(3) . . . . ? O1 C9 N2 C7 -178.48(18) . . . . ? C8 C9 N2 N3 179.0(2) . . . . ? O1 C9 N2 N3 -0.3(3) . . . . ? N1 C7 N2 C9 -0.6(3) . . . . ? C6 C7 N2 C9 178.3(2) . . . . ? N1 C7 N2 N3 -178.0(3) . . . . ? C6 C7 N2 N3 1.0(4) . . . . ? O1 C10 N3 N2 -0.2(3) . . . . ? C11 C10 N3 N2 -179.4(2) . . . . ? C9 N2 N3 C10 0.3(2) . . . . ? C7 N2 N3 C10 177.6(3) . . . . ? N5 C23 N4 C24 -0.2(3) . . . . ? C22 C23 N4 C24 179.6(2) . . . . ? C25 C24 N4 C23 0.4(3) . . . . ? C24 C25 N5 C23 0.4(3) . . . . ? O2 C25 N5 C23 -178.24(18) . . . . ? C24 C25 N5 N6 177.0(2) . . . . ? O2 C25 N5 N6 -1.7(2) . . . . ? N4 C23 N5 C25 -0.2(3) . . . . ? C22 C23 N5 C25 -179.9(2) . . . . ? N4 C23 N5 N6 -175.1(2) . . . . ? C22 C23 N5 N6 5.2(4) . . . . ? O2 C26 N6 N5 -1.0(3) . . . . ? C27 C26 N6 N5 -178.0(2) . . . . ? C25 N5 N6 C26 1.6(2) . . . . ? C23 N5 N6 C26 176.4(3) . . . . ? N2 C9 O1 C10 0.2(2) . . . . ? C8 C9 O1 C10 -178.6(4) . . . . ? N3 C10 O1 C9 0.0(3) . . . . ? C11 C10 O1 C9 179.3(2) . . . . ? C24 C25 O2 C26 -176.8(4) . . . . ? N5 C25 O2 C26 1.0(2) . . . . ? N6 C26 O2 C25 0.0(3) . . . . ? C27 C26 O2 C25 177.33(19) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 59.18 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.100 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.031 # Attachment 'I802_1f_v2.cif' data_i802 _database_code_depnum_ccdc_archive 'CCDC 743853' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 N4 O3' _chemical_formula_weight 284.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0096(2) _cell_length_b 7.1705(3) _cell_length_c 13.7650(5) _cell_angle_alpha 104.930(2) _cell_angle_beta 92.086(2) _cell_angle_gamma 98.384(2) _cell_volume 659.38(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1539 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 58.93 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.871 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2224 _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 59.21 _reflns_number_total 1519 _reflns_number_gt 1316 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0615P)^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 SHELXL _refine_ls_extinction_coef 0.0069(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1519 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1275 _refine_ls_goodness_of_fit_ref 1.606 _refine_ls_restrained_S_all 1.606 _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 C1 C 0.0730(3) 0.0520(3) 0.31812(16) 0.0567(6) Uani 1 1 d . . . C2 C 0.1807(3) 0.1696(3) 0.40326(16) 0.0580(6) Uani 1 1 d . . . H2 H 0.3151 0.1912 0.4059 0.070 Uiso 1 1 calc R . . C3 C 0.0842(3) 0.2547(3) 0.48467(16) 0.0539(6) Uani 1 1 d . . . H3 H 0.1547 0.3360 0.5424 0.065 Uiso 1 1 calc R . . C4 C -0.1159(3) 0.2210(3) 0.48181(15) 0.0499(6) Uani 1 1 d . . . C5 C -0.2206(3) 0.0976(3) 0.39480(16) 0.0600(6) Uani 1 1 d . . . H5 H -0.3549 0.0730 0.3923 0.072 Uiso 1 1 calc R . . C6 C -0.1273(3) 0.0127(3) 0.31319(16) 0.0626(6) Uani 1 1 d . . . H6 H -0.1970 -0.0699 0.2555 0.075 Uiso 1 1 calc R . . C7 C -0.2203(3) 0.3100(3) 0.56616(16) 0.0532(6) Uani 1 1 d . . . C8 C -0.4510(4) 0.4136(4) 0.65951(19) 0.0772(8) Uani 1 1 d . . . H8 H -0.5725 0.4374 0.6794 0.093 Uiso 1 1 calc R . . C9 C -0.2827(3) 0.4737(4) 0.71699(17) 0.0621(6) Uani 1 1 d . . . C10 C -0.0063(3) 0.5615(3) 0.80423(16) 0.0605(6) Uani 1 1 d . . . C11 C 0.1251(4) 0.6517(4) 0.89533(17) 0.0797(8) Uani 1 1 d . . . H11 H 0.0490 0.6919 0.9532 0.096 Uiso 1 1 calc R . . C12 C 0.2856(5) 0.8156(5) 0.8954(2) 0.1187(12) Uani 1 1 d . . . H12A H 0.2578 0.9442 0.9290 0.142 Uiso 1 1 calc R . . H12B H 0.3301 0.8126 0.8292 0.142 Uiso 1 1 calc R . . C13 C 0.4144(4) 0.7350(4) 0.9594(2) 0.0908(9) Uani 1 1 d . . . H13A H 0.5441 0.7305 0.9376 0.109 Uiso 1 1 calc R . . H13B H 0.4170 0.7951 1.0312 0.109 Uiso 1 1 calc R . . C14 C 0.2785(4) 0.5436(5) 0.9232(2) 0.1016(10) Uani 1 1 d . . . H14A H 0.2454 0.4807 0.9762 0.122 Uiso 1 1 calc R . . H14B H 0.3207 0.4529 0.8659 0.122 Uiso 1 1 calc R . . N1 N 0.1730(4) -0.0376(3) 0.23065(15) 0.0734(6) Uani 1 1 d . . . N2 N -0.1391(2) 0.4129(2) 0.66069(12) 0.0508(5) Uani 1 1 d . . . N3 N -0.4099(3) 0.3104(3) 0.56593(15) 0.0702(6) Uani 1 1 d . . . N4 N 0.0389(2) 0.4695(3) 0.71666(13) 0.0563(5) Uani 1 1 d . . . O1 O 0.0761(3) -0.1328(3) 0.15407(14) 0.1089(8) Uani 1 1 d . . . O2 O 0.3489(3) -0.0152(3) 0.23765(15) 0.1107(8) Uani 1 1 d . . . O3 O -0.1995(2) 0.5744(2) 0.81126(11) 0.0669(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0679(16) 0.0537(14) 0.0497(13) 0.0135(10) 0.0073(11) 0.0132(11) C2 0.0521(15) 0.0644(15) 0.0577(13) 0.0178(11) 0.0019(11) 0.0082(10) C3 0.0555(15) 0.0536(13) 0.0484(12) 0.0093(10) -0.0050(10) 0.0050(9) C4 0.0541(14) 0.0470(12) 0.0490(12) 0.0151(10) -0.0030(10) 0.0068(9) C5 0.0531(14) 0.0644(15) 0.0558(13) 0.0075(11) -0.0031(10) 0.0052(10) C6 0.0712(17) 0.0575(15) 0.0517(13) 0.0065(11) -0.0062(11) 0.0031(11) C7 0.0499(15) 0.0537(13) 0.0520(13) 0.0099(10) -0.0037(10) 0.0049(9) C8 0.0480(16) 0.106(2) 0.0669(16) 0.0029(14) 0.0016(12) 0.0140(13) C9 0.0550(15) 0.0736(15) 0.0524(13) 0.0067(11) 0.0055(11) 0.0113(11) C10 0.0512(15) 0.0725(16) 0.0532(14) 0.0090(12) 0.0044(10) 0.0089(10) C11 0.0586(17) 0.114(2) 0.0513(14) -0.0040(13) 0.0022(12) 0.0118(14) C12 0.120(3) 0.090(2) 0.127(3) 0.026(2) -0.059(2) -0.0228(18) C13 0.0665(19) 0.122(3) 0.0694(17) 0.0069(16) -0.0019(14) 0.0047(16) C14 0.104(2) 0.109(2) 0.0858(19) 0.0289(17) -0.0359(17) 0.0010(18) N1 0.0871(17) 0.0727(14) 0.0582(13) 0.0124(11) 0.0150(12) 0.0116(12) N2 0.0449(11) 0.0558(11) 0.0485(10) 0.0093(8) -0.0002(8) 0.0071(8) N3 0.0511(14) 0.0870(15) 0.0631(12) 0.0050(11) -0.0019(9) 0.0088(10) N4 0.0480(11) 0.0654(12) 0.0492(10) 0.0061(8) -0.0031(8) 0.0071(8) O1 0.1168(18) 0.1245(18) 0.0588(11) -0.0139(11) 0.0131(11) 0.0015(13) O2 0.0848(17) 0.148(2) 0.0868(15) 0.0006(13) 0.0246(12) 0.0288(13) O3 0.0552(11) 0.0831(12) 0.0542(10) 0.0032(8) 0.0055(7) 0.0114(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 C1 C2 1.377(3) . ? C1 C6 1.387(3) . ? C1 N1 1.466(3) . ? C2 C3 1.382(3) . ? C3 C4 1.385(3) . ? C4 C5 1.399(3) . ? C4 C7 1.452(3) . ? C5 C6 1.370(3) . ? C7 N3 1.329(3) . ? C7 N2 1.375(2) . ? C8 C9 1.346(3) . ? C8 N3 1.374(3) . ? C9 N2 1.347(3) . ? C9 O3 1.373(2) . ? C10 N4 1.291(3) . ? C10 O3 1.376(3) . ? C10 C11 1.471(3) . ? C11 C12 1.504(4) . ? C11 C14 1.507(4) . ? C12 C13 1.510(4) . ? C13 C14 1.507(4) . ? N1 O1 1.217(3) . ? N1 O2 1.217(3) . ? N2 N4 1.391(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 122.0(2) . . ? C2 C1 N1 119.1(2) . . ? C6 C1 N1 118.9(2) . . ? C1 C2 C3 118.4(2) . . ? C2 C3 C4 121.2(2) . . ? C3 C4 C5 118.9(2) . . ? C3 C4 C7 122.1(2) . . ? C5 C4 C7 119.0(2) . . ? C6 C5 C4 120.7(2) . . ? C5 C6 C1 118.8(2) . . ? N3 C7 N2 107.6(2) . . ? N3 C7 C4 126.6(2) . . ? N2 C7 C4 125.8(2) . . ? C9 C8 N3 107.2(2) . . ? C8 C9 N2 108.6(2) . . ? C8 C9 O3 144.3(2) . . ? N2 C9 O3 107.09(18) . . ? N4 C10 O3 115.20(19) . . ? N4 C10 C11 127.2(2) . . ? O3 C10 C11 117.6(2) . . ? C10 C11 C12 119.9(2) . . ? C10 C11 C14 119.7(2) . . ? C12 C11 C14 87.2(2) . . ? C11 C12 C13 89.4(2) . . ? C14 C13 C12 87.0(2) . . ? C13 C14 C11 89.4(2) . . ? O1 N1 O2 122.7(2) . . ? O1 N1 C1 118.4(2) . . ? O2 N1 C1 118.9(2) . . ? C9 N2 C7 107.83(18) . . ? C9 N2 N4 111.15(17) . . ? C7 N2 N4 141.00(18) . . ? C7 N3 C8 108.75(19) . . ? C10 N4 N2 102.76(17) . . ? C9 O3 C10 103.78(17) . . ? _diffrn_measured_fraction_theta_max 0.796 _diffrn_reflns_theta_full 59.21 _diffrn_measured_fraction_theta_full 0.796 _refine_diff_density_max 0.139 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.034