####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_riya2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C10 H8 N2 O3' _chemical_formula_sum 'C10 H8 N2 O3' _chemical_formula_weight 204.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3142(4) _cell_length_b 7.5526(2) _cell_length_c 22.9030(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1957.10(12) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25 _cell_measurement_theta_max 35 _exptl_crystal_description 'Needle shaped' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '' _exptl_absorpt_correction_T_min 0.9642 _exptl_absorpt_correction_T_max 0.9844 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'bruker axs kappa apex2 CCD diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6135 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1646 _reflns_number_gt 1340 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0576P)^2^+0.7278P] 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_number_reflns 1646 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 C1 C 0.55672(19) 0.2646(3) 0.23131(10) 0.0629(6) Uani 1 d . . . H1 H 0.4994 0.3519 0.2356 0.075 Uiso 1 calc R . . C2 C 0.5730(2) 0.1493(3) 0.18218(10) 0.0730(7) Uani 1 d . . . H2 H 0.5291 0.1489 0.1478 0.088 Uiso 1 calc R . . C3 C 0.6613(3) 0.0449(4) 0.19496(12) 0.0844(8) Uani 1 d . . . H3 H 0.6897 -0.0441 0.1707 0.101 Uiso 1 calc R . . C4 C 0.64124(16) 0.2207(2) 0.26971(8) 0.0448(5) Uani 1 d . . . C5 C 0.67033(16) 0.2932(2) 0.32592(8) 0.0448(5) Uani 1 d . . . H5 H 0.6316 0.3943 0.3390 0.054 Uiso 1 calc R . . C6 C 0.84875(14) 0.2291(2) 0.44722(8) 0.0378(4) Uani 1 d . . . C7 C 0.87137(14) 0.3232(2) 0.50192(8) 0.0409(4) Uani 1 d . . . C8 C 0.93767(17) 0.2804(3) 0.54826(9) 0.0543(5) Uani 1 d . . . H8 H 0.9821 0.1778 0.5529 0.065 Uiso 1 calc R . . C9 C 0.9272(2) 0.4205(3) 0.58856(10) 0.0646(6) Uani 1 d . . . H9 H 0.9631 0.4283 0.6250 0.078 Uiso 1 calc R . . C10 C 0.8558(2) 0.5390(3) 0.56430(10) 0.0655(6) Uani 1 d . . . H10 H 0.8340 0.6455 0.5816 0.079 Uiso 1 calc R . . N1 N 0.74858(13) 0.22046(19) 0.35805(6) 0.0423(4) Uani 1 d . . . N2 N 0.77027(13) 0.30388(18) 0.41058(6) 0.0425(4) Uani 1 d . . . H2A H 0.7347 0.4007 0.4196 0.051 Uiso 1 calc R . . O1 O 0.70638(14) 0.0838(2) 0.24871(7) 0.0741(5) Uani 1 d . . . O2 O 0.89975(11) 0.08902(16) 0.43661(6) 0.0469(4) Uani 1 d . . . O3 O 0.81910(12) 0.48411(18) 0.51086(6) 0.0562(4) 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 C1 0.0645(13) 0.0569(13) 0.0673(15) 0.0056(11) -0.0226(11) 0.0037(10) C2 0.0975(18) 0.0785(17) 0.0429(13) 0.0131(12) -0.0247(12) -0.0342(14) C3 0.106(2) 0.096(2) 0.0516(16) -0.0249(14) -0.0031(14) -0.0049(17) C4 0.0517(11) 0.0399(10) 0.0429(11) -0.0004(8) -0.0010(8) -0.0007(8) C5 0.0519(10) 0.0373(10) 0.0451(11) -0.0023(8) -0.0032(8) 0.0022(8) C6 0.0406(9) 0.0337(9) 0.0392(10) 0.0006(8) 0.0026(7) -0.0035(7) C7 0.0412(9) 0.0382(10) 0.0433(11) -0.0037(8) -0.0002(7) 0.0006(7) C8 0.0567(12) 0.0564(12) 0.0499(13) -0.0026(10) -0.0104(9) 0.0102(9) C9 0.0692(14) 0.0761(15) 0.0484(13) -0.0150(12) -0.0186(10) 0.0080(11) C10 0.0758(15) 0.0640(14) 0.0567(14) -0.0274(11) -0.0152(11) 0.0095(12) N1 0.0522(9) 0.0370(8) 0.0376(8) -0.0047(7) -0.0036(7) -0.0001(6) N2 0.0548(9) 0.0330(8) 0.0398(9) -0.0073(7) -0.0058(7) 0.0052(6) O1 0.0804(11) 0.0807(11) 0.0613(11) -0.0219(9) -0.0098(8) 0.0177(9) O2 0.0538(8) 0.0406(7) 0.0464(8) -0.0051(6) -0.0010(6) 0.0082(6) O3 0.0677(9) 0.0498(8) 0.0511(9) -0.0155(7) -0.0156(6) 0.0131(7) _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 C4 1.341(3) . ? C1 C2 1.435(3) . ? C1 H1 0.9300 . ? C2 C3 1.306(4) . ? C2 H2 0.9300 . ? C3 O1 1.365(3) . ? C3 H3 0.9300 . ? C4 O1 1.358(2) . ? C4 C5 1.437(3) . ? C5 N1 1.276(2) . ? C5 H5 0.9300 . ? C6 O2 1.230(2) . ? C6 N2 1.346(2) . ? C6 C7 1.463(2) . ? C7 C8 1.339(3) . ? C7 O3 1.367(2) . ? C8 C9 1.409(3) . ? C8 H8 0.9300 . ? C9 C10 1.327(3) . ? C9 H9 0.9300 . ? C10 O3 1.357(2) . ? C10 H10 0.9300 . ? N1 N2 1.380(2) . ? N2 H2A 0.8600 . ? 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 C4 C1 C2 105.8(2) . . ? C4 C1 H1 127.1 . . ? C2 C1 H1 127.1 . . ? C3 C2 C1 106.8(2) . . ? C3 C2 H2 126.6 . . ? C1 C2 H2 126.6 . . ? C2 C3 O1 111.0(2) . . ? C2 C3 H3 124.5 . . ? O1 C3 H3 124.5 . . ? C1 C4 O1 110.07(19) . . ? C1 C4 C5 131.04(19) . . ? O1 C4 C5 118.89(16) . . ? N1 C5 C4 120.77(17) . . ? N1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? O2 C6 N2 123.18(16) . . ? O2 C6 C7 120.35(16) . . ? N2 C6 C7 116.47(15) . . ? C8 C7 O3 109.78(16) . . ? C8 C7 C6 131.24(17) . . ? O3 C7 C6 118.98(15) . . ? C7 C8 C9 106.88(18) . . ? C7 C8 H8 126.6 . . ? C9 C8 H8 126.6 . . ? C10 C9 C8 106.48(19) . . ? C10 C9 H9 126.8 . . ? C8 C9 H9 126.8 . . ? C9 C10 O3 110.94(19) . . ? C9 C10 H10 124.5 . . ? O3 C10 H10 124.5 . . ? C5 N1 N2 115.45(15) . . ? C6 N2 N1 118.00(14) . . ? C6 N2 H2A 121.0 . . ? N1 N2 H2A 121.0 . . ? C4 O1 C3 106.30(19) . . ? C10 O3 C7 105.92(15) . . ? 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 C4 C1 C2 C3 1.6(3) . . . . ? C1 C2 C3 O1 -0.9(3) . . . . ? C2 C1 C4 O1 -1.7(2) . . . . ? C2 C1 C4 C5 178.3(2) . . . . ? C1 C4 C5 N1 173.6(2) . . . . ? O1 C4 C5 N1 -6.4(3) . . . . ? O2 C6 C7 C8 -4.1(3) . . . . ? N2 C6 C7 C8 175.61(19) . . . . ? O2 C6 C7 O3 175.91(15) . . . . ? N2 C6 C7 O3 -4.4(2) . . . . ? O3 C7 C8 C9 0.0(2) . . . . ? C6 C7 C8 C9 179.99(19) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C8 C9 C10 O3 0.2(3) . . . . ? C4 C5 N1 N2 178.91(16) . . . . ? O2 C6 N2 N1 -1.6(2) . . . . ? C7 C6 N2 N1 178.73(14) . . . . ? C5 N1 N2 C6 177.51(15) . . . . ? C1 C4 O1 C3 1.2(3) . . . . ? C5 C4 O1 C3 -178.8(2) . . . . ? C2 C3 O1 C4 -0.1(3) . . . . ? C9 C10 O3 C7 -0.3(3) . . . . ? C8 C7 O3 C10 0.2(2) . . . . ? C6 C7 O3 C10 -179.84(17) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.223 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 953906'