data_lar08 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 N2 O' _chemical_formula_weight 196.20 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 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 7.4164(18) _cell_length_b 12.426(3) _cell_length_c 20.103(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1852.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 942 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 27.82 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 16749 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4330 _reflns_number_gt 3998 _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^)+(0.0445P)^2^+0.2943P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(11) _refine_ls_number_reflns 4330 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.5185(2) 0.15374(12) 0.43738(7) 0.0351(3) Uani 1 1 d . . . C2 C 0.52346(19) 0.06720(11) 0.38922(7) 0.0294(3) Uani 1 1 d . . . C3 C 0.58536(19) 0.08594(11) 0.32525(7) 0.0268(3) Uani 1 1 d . . . C4 C 0.59131(17) 0.00011(10) 0.28027(7) 0.0251(3) Uani 1 1 d . . . C5 C 0.65333(17) 0.01193(10) 0.21072(7) 0.0253(3) Uani 1 1 d . . . C6 C 0.7092(2) 0.11222(11) 0.18603(7) 0.0303(3) Uani 1 1 d . . . C7 C 0.7657(2) 0.12564(12) 0.12118(7) 0.0338(3) Uani 1 1 d . . . C8 C 0.7675(2) 0.03742(13) 0.07849(7) 0.0363(3) Uani 1 1 d . . . C9 C 0.7157(2) -0.06207(13) 0.10100(7) 0.0367(3) Uani 1 1 d . . . C10 C 0.65861(19) -0.07658(11) 0.16652(7) 0.0304(3) Uani 1 1 d . . . C11 C 0.4789(2) -0.11570(12) 0.36115(7) 0.0350(3) Uani 1 1 d . . . C12 C 0.4682(2) -0.03543(12) 0.40824(7) 0.0338(3) Uani 1 1 d . . . C13 C 0.2932(2) 0.15034(12) 0.06229(7) 0.0364(3) Uani 1 1 d . . . C14 C 0.24770(18) 0.06208(11) 0.10628(7) 0.0294(3) Uani 1 1 d . . . C15 C 0.19424(19) 0.08268(11) 0.17122(7) 0.0280(3) Uani 1 1 d . . . C16 C 0.14596(17) -0.00367(10) 0.21207(7) 0.0255(3) Uani 1 1 d . . . C17 C 0.09080(17) 0.01000(10) 0.28233(7) 0.0250(3) Uani 1 1 d . . . C18 C 0.1113(2) 0.10947(11) 0.31432(7) 0.0295(3) Uani 1 1 d . . . C19 C 0.0616(2) 0.12429(12) 0.37999(7) 0.0340(3) Uani 1 1 d . . . C20 C -0.0118(2) 0.03900(13) 0.41538(7) 0.0353(3) Uani 1 1 d . . . C21 C -0.0323(2) -0.06014(13) 0.38590(7) 0.0346(3) Uani 1 1 d . . . C22 C 0.01853(18) -0.07617(11) 0.31979(7) 0.0290(3) Uani 1 1 d . . . C23 C 0.1989(2) -0.12346(12) 0.12521(7) 0.0347(3) Uani 1 1 d . . . C24 C 0.2526(2) -0.04334(12) 0.08241(7) 0.0337(3) Uani 1 1 d . . . N1 N 0.5163(2) 0.22012(11) 0.47676(6) 0.0476(4) Uani 1 1 d . . . N2 N 0.53769(17) -0.09917(9) 0.29915(6) 0.0305(3) Uani 1 1 d . . . N3 N 0.3257(2) 0.21939(12) 0.02668(7) 0.0524(4) Uani 1 1 d . . . N4 N 0.14716(17) -0.10531(9) 0.18788(6) 0.0310(3) Uani 1 1 d . . . O1 O 0.60925(17) -0.17717(8) 0.18475(6) 0.0405(3) Uani 1 1 d . . . O2 O -0.00598(17) -0.17576(8) 0.29392(5) 0.0402(3) Uani 1 1 d . . . H3 H 0.625(2) 0.1568(13) 0.3128(7) 0.033(4) Uiso 1 1 d . . . H6 H 0.708(2) 0.1733(13) 0.2156(8) 0.033(4) Uiso 1 1 d . . . H7 H 0.804(2) 0.1968(14) 0.1064(8) 0.041(4) Uiso 1 1 d . . . H8 H 0.803(2) 0.0490(13) 0.0318(9) 0.040(4) Uiso 1 1 d . . . H9 H 0.717(2) -0.1238(14) 0.0709(9) 0.043(5) Uiso 1 1 d . . . H11 H 0.440(2) -0.1869(14) 0.3714(7) 0.035(4) Uiso 1 1 d . . . H12 H 0.425(2) -0.0502(13) 0.4523(8) 0.032(4) Uiso 1 1 d . . . H15 H 0.184(2) 0.1545(13) 0.1867(8) 0.033(4) Uiso 1 1 d . . . H18 H 0.161(2) 0.1679(12) 0.2905(7) 0.024(4) Uiso 1 1 d . . . H19 H 0.077(2) 0.1946(15) 0.4008(8) 0.045(5) Uiso 1 1 d . . . H20 H -0.045(2) 0.0488(14) 0.4624(9) 0.040(5) Uiso 1 1 d . . . H21 H -0.082(3) -0.1198(16) 0.4108(9) 0.047(5) Uiso 1 1 d . . . H23 H 0.195(2) -0.1980(13) 0.1113(8) 0.036(4) Uiso 1 1 d . . . H24 H 0.290(2) -0.0590(13) 0.0362(8) 0.035(4) Uiso 1 1 d . . . H1O H 0.578(3) -0.1723(15) 0.2272(10) 0.046(5) Uiso 1 1 d . . . H2O H 0.050(3) -0.1703(18) 0.2519(10) 0.066(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0453(8) 0.0372(7) 0.0226(6) 0.0037(5) 0.0009(6) 0.0000(6) C2 0.0302(7) 0.0311(7) 0.0267(6) 0.0003(5) -0.0025(5) 0.0032(5) C3 0.0304(7) 0.0235(6) 0.0264(6) 0.0027(5) -0.0019(5) 0.0020(5) C4 0.0229(6) 0.0251(6) 0.0273(6) 0.0022(5) -0.0038(5) 0.0029(5) C5 0.0223(6) 0.0273(6) 0.0264(6) -0.0008(5) -0.0027(5) 0.0050(5) C6 0.0315(7) 0.0307(7) 0.0288(7) -0.0012(5) 0.0003(5) 0.0025(5) C7 0.0324(7) 0.0365(7) 0.0323(7) 0.0037(6) 0.0010(6) 0.0018(6) C8 0.0317(8) 0.0516(9) 0.0255(7) -0.0027(6) 0.0018(6) 0.0053(7) C9 0.0379(8) 0.0401(8) 0.0320(8) -0.0121(6) -0.0017(6) 0.0064(6) C10 0.0295(7) 0.0291(7) 0.0325(7) -0.0040(5) -0.0048(6) 0.0062(5) C11 0.0394(8) 0.0291(7) 0.0365(7) 0.0071(6) -0.0033(6) -0.0047(6) C12 0.0330(7) 0.0401(8) 0.0284(7) 0.0080(6) -0.0002(6) -0.0033(6) C13 0.0426(8) 0.0405(8) 0.0260(7) -0.0005(6) -0.0013(6) 0.0014(6) C14 0.0268(7) 0.0352(7) 0.0262(7) 0.0008(5) -0.0032(5) 0.0022(6) C15 0.0306(7) 0.0262(6) 0.0272(6) -0.0016(5) -0.0032(5) 0.0026(5) C16 0.0230(6) 0.0260(6) 0.0276(6) -0.0025(5) -0.0029(5) 0.0036(5) C17 0.0246(6) 0.0260(6) 0.0245(6) 0.0001(5) -0.0037(5) 0.0030(5) C18 0.0321(7) 0.0276(7) 0.0289(7) 0.0001(5) -0.0020(5) 0.0001(5) C19 0.0362(8) 0.0359(7) 0.0300(7) -0.0075(6) -0.0038(6) 0.0027(6) C20 0.0307(7) 0.0503(9) 0.0249(6) 0.0005(6) -0.0023(6) 0.0055(6) C21 0.0308(7) 0.0410(8) 0.0319(7) 0.0098(6) -0.0005(6) 0.0009(6) C22 0.0270(7) 0.0277(7) 0.0323(6) 0.0025(5) -0.0033(6) 0.0030(5) C23 0.0374(8) 0.0293(7) 0.0374(8) -0.0085(6) 0.0014(6) 0.0037(6) C24 0.0317(7) 0.0416(8) 0.0280(7) -0.0073(6) 0.0008(6) 0.0035(6) N1 0.0737(10) 0.0430(7) 0.0261(6) -0.0016(5) 0.0022(7) -0.0014(7) N2 0.0326(6) 0.0256(5) 0.0333(6) 0.0023(5) -0.0035(5) -0.0004(5) N3 0.0733(11) 0.0498(8) 0.0339(7) 0.0070(6) 0.0016(7) -0.0025(8) N4 0.0325(6) 0.0273(6) 0.0333(6) -0.0044(5) -0.0001(5) 0.0017(5) O1 0.0587(7) 0.0256(5) 0.0372(6) -0.0070(4) -0.0015(5) 0.0015(5) O2 0.0545(7) 0.0245(5) 0.0415(6) 0.0010(4) 0.0053(5) -0.0041(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 C1 N1 1.1434(19) . ? C1 C2 1.4473(19) . ? C2 C3 1.3853(19) . ? C2 C12 1.393(2) . ? C3 C4 1.3989(18) . ? C3 H3 0.961(16) . ? C4 N2 1.3507(17) . ? C4 C5 1.4790(19) . ? C5 C6 1.4040(19) . ? C5 C10 1.4145(18) . ? C6 C7 1.380(2) . ? C6 H6 0.964(16) . ? C7 C8 1.392(2) . ? C7 H7 0.976(18) . ? C8 C9 1.371(2) . ? C8 H8 0.984(18) . ? C9 C10 1.395(2) . ? C9 H9 0.977(17) . ? C10 O1 1.3531(18) . ? C11 N2 1.3360(18) . ? C11 C12 1.377(2) . ? C11 H11 0.954(17) . ? C12 H12 0.959(16) . ? C13 N3 1.143(2) . ? C13 C14 1.449(2) . ? C14 C15 1.3882(19) . ? C14 C24 1.396(2) . ? C15 C16 1.3978(18) . ? C15 H15 0.948(16) . ? C16 N4 1.3533(17) . ? C16 C17 1.4803(19) . ? C17 C18 1.4016(18) . ? C17 C22 1.4145(19) . ? C18 C19 1.3831(19) . ? C18 H18 0.946(15) . ? C19 C20 1.388(2) . ? C19 H19 0.976(19) . ? C20 C21 1.376(2) . ? C20 H20 0.984(17) . ? C21 C22 1.396(2) . ? C21 H21 0.966(19) . ? C22 O2 1.3547(17) . ? C23 N4 1.3362(19) . ? C23 C24 1.375(2) . ? C23 H23 0.968(17) . ? C24 H24 0.988(16) . ? O1 H1O 0.886(19) . ? O2 H2O 0.94(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 N1 C1 C2 178.06(15) . . ? C3 C2 C12 120.41(12) . . ? C3 C2 C1 120.30(13) . . ? C12 C2 C1 119.29(13) . . ? C2 C3 C4 118.84(12) . . ? C2 C3 H3 119.7(9) . . ? C4 C3 H3 121.4(9) . . ? N2 C4 C3 120.36(12) . . ? N2 C4 C5 116.61(11) . . ? C3 C4 C5 123.03(11) . . ? C6 C5 C10 117.38(12) . . ? C6 C5 C4 120.94(11) . . ? C10 C5 C4 121.68(12) . . ? C7 C6 C5 122.08(13) . . ? C7 C6 H6 119.4(10) . . ? C5 C6 H6 118.5(9) . . ? C6 C7 C8 119.34(14) . . ? C6 C7 H7 119.1(10) . . ? C8 C7 H7 121.5(10) . . ? C9 C8 C7 120.26(13) . . ? C9 C8 H8 121.4(10) . . ? C7 C8 H8 118.3(10) . . ? C8 C9 C10 120.85(13) . . ? C8 C9 H9 120.1(10) . . ? C10 C9 H9 119.0(10) . . ? O1 C10 C9 117.20(12) . . ? O1 C10 C5 122.73(13) . . ? C9 C10 C5 120.07(13) . . ? N2 C11 C12 123.27(13) . . ? N2 C11 H11 116.3(9) . . ? C12 C11 H11 120.4(9) . . ? C11 C12 C2 117.21(13) . . ? C11 C12 H12 121.0(10) . . ? C2 C12 H12 121.7(10) . . ? N3 C13 C14 178.38(17) . . ? C15 C14 C24 120.26(13) . . ? C15 C14 C13 120.07(13) . . ? C24 C14 C13 119.64(13) . . ? C14 C15 C16 118.95(12) . . ? C14 C15 H15 120.4(10) . . ? C16 C15 H15 120.6(10) . . ? N4 C16 C15 120.24(12) . . ? N4 C16 C17 116.86(11) . . ? C15 C16 C17 122.90(11) . . ? C18 C17 C22 117.68(12) . . ? C18 C17 C16 120.60(12) . . ? C22 C17 C16 121.72(11) . . ? C19 C18 C17 121.76(13) . . ? C19 C18 H18 119.1(9) . . ? C17 C18 H18 119.2(9) . . ? C18 C19 C20 119.49(14) . . ? C18 C19 H19 119.8(10) . . ? C20 C19 H19 120.7(10) . . ? C21 C20 C19 120.43(13) . . ? C21 C20 H20 119.8(10) . . ? C19 C20 H20 119.7(10) . . ? C20 C21 C22 120.54(14) . . ? C20 C21 H21 120.4(11) . . ? C22 C21 H21 119.1(11) . . ? O2 C22 C21 117.36(13) . . ? O2 C22 C17 122.55(12) . . ? C21 C22 C17 120.08(13) . . ? N4 C23 C24 123.44(13) . . ? N4 C23 H23 115.2(10) . . ? C24 C23 H23 121.4(10) . . ? C23 C24 C14 117.19(13) . . ? C23 C24 H24 121.8(9) . . ? C14 C24 H24 121.0(10) . . ? C11 N2 C4 119.90(12) . . ? C23 N4 C16 119.88(12) . . ? C10 O1 H1O 105.6(13) . . ? C22 O2 H2O 102.6(14) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.270 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.035