data_bashir3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N3 O2' _chemical_formula_sum 'C11 H11 N3 O2' _chemical_formula_weight 217.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 18.987(4) _cell_length_b 24.295(5) _cell_length_c 9.2123(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4249.6(13) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3122 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.96 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '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 6739 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 28.12 _reflns_number_total 1459 _reflns_number_gt 1394 _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^)+(0.0521P)^2^+3.9798P] 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 mixed _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 0.00 _refine_ls_number_reflns 1459 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.12232(8) 0.24636(7) 0.89781(17) 0.0193(4) Uani 1 1 d . . . O2 O -0.03890(9) 0.24653(8) 0.91983(19) 0.0250(4) Uani 1 1 d . . . N1 N 0.12835(10) 0.26799(8) 0.6568(2) 0.0171(4) Uani 1 1 d . . . H1N1 H 0.1088(13) 0.2634(10) 0.574(3) 0.013(6) Uiso 1 1 d . . . N2 N 0.04202(12) 0.11688(10) 0.8906(3) 0.0296(5) Uani 1 1 d . . . N3 N -0.07015(12) 0.25896(9) 0.6860(2) 0.0220(5) Uani 1 1 d . . . H1N3 H -0.0587(14) 0.2546(11) 0.604(4) 0.021(8) Uiso 1 1 d . . . C1 C 0.10160(12) 0.24234(9) 0.7746(3) 0.0159(5) Uani 1 1 d . . . C2 C 0.03583(12) 0.20726(10) 0.7389(2) 0.0168(5) Uani 1 1 d . . . H2 H 0.0332 0.1990 0.6326 0.020 Uiso 1 1 calc R . . C3 C -0.02937(13) 0.23993(11) 0.7895(3) 0.0189(5) Uani 1 1 d . . . C4 C 0.03944(12) 0.15631(11) 0.8243(3) 0.0210(5) Uani 1 1 d . . . C5 C -0.13337(14) 0.29022(13) 0.7173(3) 0.0302(6) Uani 1 1 d . . . H51 H -0.1724 0.2649 0.7364 0.045 Uiso 1 1 calc R . . H52 H -0.1450 0.3135 0.6338 0.045 Uiso 1 1 calc R . . H53 H -0.1254 0.3134 0.8028 0.045 Uiso 1 1 calc R . . C6 C 0.18684(12) 0.30394(9) 0.6525(3) 0.0157(5) Uani 1 1 d . . . C7 C 0.22619(12) 0.31811(10) 0.7739(3) 0.0179(5) Uani 1 1 d . . . H7 H 0.2144 0.3036 0.8666 0.022 Uiso 1 1 calc R . . C8 C 0.28247(12) 0.35344(10) 0.7587(3) 0.0203(5) Uani 1 1 d . . . H8 H 0.3092 0.3636 0.8416 0.024 Uiso 1 1 calc R . . C9 C 0.30043(13) 0.37429(10) 0.6241(3) 0.0244(6) Uani 1 1 d . . . H9 H 0.3397 0.3983 0.6149 0.029 Uiso 1 1 calc R . . C10 C 0.26157(14) 0.36043(11) 0.5035(3) 0.0244(6) Uani 1 1 d . . . H10 H 0.2739 0.3749 0.4112 0.029 Uiso 1 1 calc R . . C11 C 0.20448(13) 0.32530(11) 0.5167(3) 0.0214(5) Uani 1 1 d . . . H11 H 0.1774 0.3158 0.4337 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0202(9) 0.0253(9) 0.0125(8) -0.0004(7) -0.0010(6) -0.0020(7) O2 0.0222(9) 0.0410(11) 0.0119(8) -0.0024(7) 0.0032(7) -0.0013(8) N1 0.0188(11) 0.0227(10) 0.0099(10) -0.0006(8) -0.0028(8) -0.0023(8) N2 0.0352(13) 0.0288(12) 0.0247(12) 0.0031(10) 0.0027(10) -0.0064(10) N3 0.0220(12) 0.0299(12) 0.0142(11) -0.0030(9) 0.0013(8) 0.0010(10) C1 0.0146(11) 0.0161(11) 0.0171(10) -0.0029(9) 0.0010(9) 0.0024(10) C2 0.0182(12) 0.0215(13) 0.0108(10) -0.0009(8) 0.0010(8) -0.0045(10) C3 0.0171(12) 0.0224(13) 0.0170(11) -0.0009(9) 0.0011(9) -0.0056(10) C4 0.0181(12) 0.0282(14) 0.0166(12) -0.0021(10) 0.0026(9) -0.0053(11) C5 0.0265(14) 0.0394(16) 0.0247(13) -0.0014(11) -0.0001(11) 0.0096(13) C6 0.0134(11) 0.0130(11) 0.0207(11) 0.0000(9) 0.0031(9) 0.0033(9) C7 0.0165(11) 0.0193(12) 0.0180(11) 0.0005(9) 0.0032(9) 0.0049(10) C8 0.0160(12) 0.0200(12) 0.0248(12) -0.0047(10) -0.0009(10) 0.0017(10) C9 0.0189(13) 0.0211(12) 0.0331(16) 0.0012(10) 0.0050(11) -0.0012(11) C10 0.0268(14) 0.0246(13) 0.0219(12) 0.0045(10) 0.0073(10) -0.0002(11) C11 0.0239(13) 0.0239(13) 0.0163(12) 0.0020(10) 0.0016(10) 0.0002(11) _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 C1 1.205(3) . ? O2 C3 1.224(3) . ? N1 C1 1.351(3) . ? N1 C6 1.413(3) . ? N1 H1N1 0.85(3) . ? N2 C4 1.137(3) . ? N3 C3 1.312(3) . ? N3 C5 1.449(3) . ? N3 H1N3 0.79(3) . ? C1 C2 1.547(3) . ? C2 C4 1.469(3) . ? C2 C3 1.543(3) . ? C2 H2 1.0000 . ? C5 H51 0.9800 . ? C5 H52 0.9800 . ? C5 H53 0.9800 . ? C6 C7 1.388(3) . ? C6 C11 1.395(3) . ? C7 C8 1.378(4) . ? C7 H7 0.9500 . ? C8 C9 1.382(4) . ? C8 H8 0.9500 . ? C9 C10 1.376(4) . ? C9 H9 0.9500 . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? 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 C1 N1 C6 127.1(2) . . ? C1 N1 H1N1 119.5(18) . . ? C6 N1 H1N1 113.4(17) . . ? C3 N3 C5 121.9(2) . . ? C3 N3 H1N3 119(2) . . ? C5 N3 H1N3 119(2) . . ? O1 C1 N1 126.6(2) . . ? O1 C1 C2 120.6(2) . . ? N1 C1 C2 112.8(2) . . ? C4 C2 C3 107.97(19) . . ? C4 C2 C1 108.22(19) . . ? C3 C2 C1 107.45(19) . . ? C4 C2 H2 111.0 . . ? C3 C2 H2 111.0 . . ? C1 C2 H2 111.0 . . ? O2 C3 N3 125.4(3) . . ? O2 C3 C2 118.9(2) . . ? N3 C3 C2 115.8(2) . . ? N2 C4 C2 179.8(3) . . ? N3 C5 H51 109.5 . . ? N3 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? N3 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 109.5 . . ? C7 C6 C11 120.1(2) . . ? C7 C6 N1 123.6(2) . . ? C11 C6 N1 116.3(2) . . ? C8 C7 C6 119.3(2) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 120.8(2) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.0(2) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 119.7(2) . . ? C10 C11 H11 120.1 . . ? C6 C11 H11 120.1 . . ? 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 N3 H1N3 O1 0.79(3) 2.25(3) 2.837(3) 131(3) 6_554 N1 H1N1 O2 0.85(3) 1.96(3) 2.788(3) 163(3) 6_554 _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 28.12 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.231 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.049