data_2191 _audit_creation_method 'SHELXL-97 & ZCIF' _chemical_name_systematic ; Organic ; _chemical_name_common Organic _chemical_formula_moiety 'C12 H10 N2 O6' _chemical_formula_sum 'C12 H10 N2 O6' _chemical_formula_weight 278.22 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 P21/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 6.8882(5) _cell_length_b 20.8439(15) _cell_length_c 8.2554(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.0280(10) _cell_angle_gamma 90.00 _cell_volume 1185.29(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12115 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 31.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.095 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _diffrn_ambient_temperature 150(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 'three-circle diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 11.198 _diffrn_reflns_number 17592 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3452 _reflns_number_gt 3196 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2010)' _computing_cell_refinement Apex2 _computing_data_reduction Apex2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _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 _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.01P)^2^+0.809P], P=(max(Fo^2^,0)+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_number_reflns 3452 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.84266(11) 0.12124(4) 0.51870(10) 0.02633(17) Uani 1 1 d . . . O2 O 0.79675(12) 0.16749(4) 0.28704(10) 0.02923(19) Uani 1 1 d . . . N3 N 0.74603(12) 0.13117(4) 0.39619(10) 0.01896(17) Uani 1 1 d . . . C4 C 0.55717(14) 0.09844(5) 0.38222(11) 0.01638(17) Uani 1 1 d . . . C5 C 0.46468(15) 0.08402(5) 0.52704(12) 0.01960(19) Uani 1 1 d . . . H5 H 0.523(2) 0.0953(7) 0.6261(17) 0.027(3) Uiso 1 1 d . . . C6 C 0.28351(16) 0.05503(5) 0.52302(13) 0.0227(2) Uani 1 1 d . . . H6 H 0.218(2) 0.0459(7) 0.6266(18) 0.029(4) Uiso 1 1 d . . . C7 C 0.20088(16) 0.03868(5) 0.37519(13) 0.0227(2) Uani 1 1 d . . . H7 H 0.077(2) 0.0170(7) 0.3692(17) 0.028(4) Uiso 1 1 d . . . C8 C 0.29701(15) 0.05248(5) 0.23086(12) 0.01934(19) Uani 1 1 d . . . H8 H 0.243(2) 0.0405(7) 0.1334(17) 0.025(3) Uiso 1 1 d . . . C9 C 0.47552(14) 0.08401(5) 0.23115(11) 0.01573(17) Uani 1 1 d . . . C10 C 0.56841(14) 0.09925(5) 0.07291(11) 0.01602(17) Uani 1 1 d . . . N11 N 0.46109(13) 0.10460(4) -0.07697(10) 0.01848(16) Uani 1 1 d . . . H11 H 0.334(2) 0.1073(7) -0.0609(17) 0.027(4) Uiso 1 1 d . . . C12 C 0.56796(14) 0.16186(5) -0.01539(11) 0.01739(18) Uani 1 1 d . . . C13 C 0.76555(15) 0.16863(5) -0.09055(12) 0.0211(2) Uani 1 1 d . . . H131 H 0.839(2) 0.2036(7) -0.0418(17) 0.028(4) Uiso 1 1 d . . . H132 H 0.763(2) 0.1741(7) -0.2062(18) 0.029(4) Uiso 1 1 d . . . C14 C 0.86539(15) 0.10596(6) -0.05004(12) 0.0215(2) Uani 1 1 d . . . O15 O 0.75209(10) 0.06896(4) 0.05008(9) 0.01978(15) Uani 1 1 d . . . O16 O 1.02141(11) 0.08727(5) -0.09446(10) 0.03027(19) Uani 1 1 d . . . C17 C 0.46904(15) 0.21948(5) 0.05188(12) 0.01968(19) Uani 1 1 d . . . O18 O 0.55089(13) 0.26968(4) 0.07538(12) 0.03185(19) Uani 1 1 d . . . O19 O 0.28179(11) 0.20857(4) 0.08428(10) 0.02402(16) Uani 1 1 d . . . C20 C 0.17527(19) 0.26248(6) 0.15180(18) 0.0315(3) Uani 1 1 d . . . H201 H 0.055(3) 0.2442(8) 0.188(2) 0.049(5) Uiso 1 1 d . . . H202 H 0.157(3) 0.2942(9) 0.073(2) 0.048(5) Uiso 1 1 d . . . H203 H 0.252(3) 0.2825(9) 0.240(2) 0.060(5) 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 O1 0.0223(4) 0.0354(4) 0.0213(4) -0.0011(3) -0.0067(3) 0.0011(3) O2 0.0309(4) 0.0377(5) 0.0192(4) 0.0029(3) -0.0002(3) -0.0153(4) N3 0.0186(4) 0.0230(4) 0.0153(4) -0.0036(3) 0.0003(3) -0.0012(3) C4 0.0169(4) 0.0173(4) 0.0149(4) -0.0005(3) 0.0004(3) -0.0007(3) C5 0.0247(5) 0.0210(5) 0.0131(4) -0.0007(3) 0.0015(3) 0.0002(4) C6 0.0251(5) 0.0247(5) 0.0181(5) 0.0018(4) 0.0064(4) -0.0021(4) C7 0.0204(5) 0.0250(5) 0.0228(5) 0.0020(4) 0.0034(4) -0.0047(4) C8 0.0202(5) 0.0213(5) 0.0165(4) -0.0002(4) -0.0005(3) -0.0027(4) C9 0.0178(4) 0.0165(4) 0.0129(4) -0.0001(3) 0.0012(3) 0.0002(3) C10 0.0155(4) 0.0200(4) 0.0126(4) -0.0016(3) 0.0009(3) -0.0001(3) N11 0.0164(4) 0.0258(4) 0.0132(4) -0.0013(3) -0.0007(3) -0.0019(3) C12 0.0170(4) 0.0222(5) 0.0130(4) 0.0009(3) 0.0005(3) -0.0016(3) C13 0.0177(4) 0.0300(5) 0.0155(4) 0.0019(4) 0.0022(3) -0.0037(4) C14 0.0171(4) 0.0333(5) 0.0141(4) -0.0030(4) -0.0006(3) -0.0020(4) O15 0.0167(3) 0.0249(4) 0.0177(3) -0.0013(3) 0.0019(2) 0.0027(3) O16 0.0168(4) 0.0485(5) 0.0255(4) -0.0028(4) 0.0030(3) 0.0035(3) C17 0.0208(5) 0.0220(5) 0.0162(4) 0.0039(4) 0.0000(3) 0.0004(4) O18 0.0292(4) 0.0221(4) 0.0443(5) -0.0003(4) 0.0038(4) -0.0037(3) O19 0.0199(4) 0.0242(4) 0.0280(4) -0.0043(3) 0.0036(3) 0.0005(3) C20 0.0258(6) 0.0293(6) 0.0393(7) -0.0086(5) 0.0050(5) 0.0040(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 O1 N3 1.2280(11) . ? O2 N3 1.2278(12) . ? N3 C4 1.4734(13) . ? C4 C5 1.3879(13) . ? C4 C9 1.4005(13) . ? C5 C6 1.3869(15) . ? C5 H5 0.941(14) . ? C6 C7 1.3888(15) . ? C6 H6 0.985(15) . ? C7 C8 1.3934(14) . ? C7 H7 0.969(15) . ? C8 C9 1.3942(13) . ? C8 H8 0.920(14) . ? C9 C10 1.4892(13) . ? C10 O15 1.4266(11) . ? C10 N11 1.4453(12) . ? C10 C12 1.4949(14) . ? N11 C12 1.4914(13) . ? N11 H11 0.886(14) . ? C12 C17 1.4884(14) . ? C12 C13 1.5027(14) . ? C13 C14 1.5135(16) . ? C13 H131 0.975(15) . ? C13 H132 0.961(15) . ? C14 O16 1.2007(13) . ? C14 O15 1.3738(13) . ? C17 O18 1.2043(13) . ? C17 O19 1.3368(12) . ? O19 C20 1.4533(14) . ? C20 H201 0.961(18) . ? C20 H202 0.936(18) . ? C20 H203 0.99(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 O2 N3 O1 123.65(9) . . ? O2 N3 C4 118.66(8) . . ? O1 N3 C4 117.68(8) . . ? C5 C4 C9 122.43(9) . . ? C5 C4 N3 116.01(9) . . ? C9 C4 N3 121.55(8) . . ? C6 C5 C4 119.15(9) . . ? C6 C5 H5 120.9(9) . . ? C4 C5 H5 119.9(9) . . ? C5 C6 C7 119.76(9) . . ? C5 C6 H6 118.4(9) . . ? C7 C6 H6 121.9(9) . . ? C6 C7 C8 120.40(10) . . ? C6 C7 H7 121.4(9) . . ? C8 C7 H7 118.2(9) . . ? C7 C8 C9 121.02(9) . . ? C7 C8 H8 120.1(9) . . ? C9 C8 H8 118.9(9) . . ? C8 C9 C4 117.16(9) . . ? C8 C9 C10 118.58(8) . . ? C4 C9 C10 124.25(9) . . ? O15 C10 N11 111.98(8) . . ? O15 C10 C9 113.77(8) . . ? N11 C10 C9 123.21(8) . . ? O15 C10 C12 108.88(8) . . ? N11 C10 C12 60.94(6) . . ? C9 C10 C12 127.82(8) . . ? C10 N11 C12 61.17(6) . . ? C10 N11 H11 112.4(9) . . ? C12 N11 H11 112.6(9) . . ? C17 C12 N11 123.16(8) . . ? C17 C12 C10 121.55(8) . . ? N11 C12 C10 57.89(6) . . ? C17 C12 C13 119.55(9) . . ? N11 C12 C13 112.42(8) . . ? C10 C12 C13 106.36(8) . . ? C12 C13 C14 103.85(8) . . ? C12 C13 H131 111.9(8) . . ? C14 C13 H131 108.4(8) . . ? C12 C13 H132 114.0(9) . . ? C14 C13 H132 109.2(9) . . ? H131 C13 H132 109.2(12) . . ? O16 C14 O15 120.69(11) . . ? O16 C14 C13 128.26(10) . . ? O15 C14 C13 111.05(8) . . ? C14 O15 C10 109.58(8) . . ? O18 C17 O19 124.56(10) . . ? O18 C17 C12 123.15(10) . . ? O19 C17 C12 112.29(9) . . ? C17 O19 C20 115.63(9) . . ? O19 C20 H201 104.4(10) . . ? O19 C20 H202 110.4(11) . . ? H201 C20 H202 112.2(15) . . ? O19 C20 H203 109.8(11) . . ? H201 C20 H203 113.5(15) . . ? H202 C20 H203 106.6(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 O2 N3 C4 C5 -150.49(10) . . . . ? O1 N3 C4 C5 28.30(13) . . . . ? O2 N3 C4 C9 28.39(14) . . . . ? O1 N3 C4 C9 -152.83(9) . . . . ? C9 C4 C5 C6 -0.88(15) . . . . ? N3 C4 C5 C6 177.98(9) . . . . ? C4 C5 C6 C7 2.45(16) . . . . ? C5 C6 C7 C8 -1.39(17) . . . . ? C6 C7 C8 C9 -1.31(17) . . . . ? C7 C8 C9 C4 2.80(15) . . . . ? C7 C8 C9 C10 -178.14(10) . . . . ? C5 C4 C9 C8 -1.72(15) . . . . ? N3 C4 C9 C8 179.48(9) . . . . ? C5 C4 C9 C10 179.27(9) . . . . ? N3 C4 C9 C10 0.47(15) . . . . ? C8 C9 C10 O15 -118.27(10) . . . . ? C4 C9 C10 O15 60.72(13) . . . . ? C8 C9 C10 N11 22.72(14) . . . . ? C4 C9 C10 N11 -158.29(9) . . . . ? C8 C9 C10 C12 99.60(12) . . . . ? C4 C9 C10 C12 -81.40(13) . . . . ? O15 C10 N11 C12 -100.07(9) . . . . ? C9 C10 N11 C12 118.34(10) . . . . ? C10 N11 C12 C17 -109.15(10) . . . . ? C10 N11 C12 C13 95.78(9) . . . . ? O15 C10 C12 C17 -142.92(9) . . . . ? N11 C10 C12 C17 111.86(10) . . . . ? C9 C10 C12 C17 0.65(15) . . . . ? O15 C10 C12 N11 105.22(8) . . . . ? C9 C10 C12 N11 -111.21(11) . . . . ? O15 C10 C12 C13 -1.34(10) . . . . ? N11 C10 C12 C13 -106.56(9) . . . . ? C9 C10 C12 C13 142.23(10) . . . . ? C17 C12 C13 C14 146.45(9) . . . . ? N11 C12 C13 C14 -57.48(10) . . . . ? C10 C12 C13 C14 3.95(10) . . . . ? C12 C13 C14 O16 174.19(11) . . . . ? C12 C13 C14 O15 -5.55(11) . . . . ? O16 C14 O15 C10 -174.84(9) . . . . ? C13 C14 O15 C10 4.93(11) . . . . ? N11 C10 O15 C14 63.24(10) . . . . ? C9 C10 O15 C14 -151.37(8) . . . . ? C12 C10 O15 C14 -2.20(10) . . . . ? N11 C12 C17 O18 -166.69(10) . . . . ? C10 C12 C17 O18 123.42(11) . . . . ? C13 C12 C17 O18 -13.30(15) . . . . ? N11 C12 C17 O19 14.05(13) . . . . ? C10 C12 C17 O19 -55.84(12) . . . . ? C13 C12 C17 O19 167.44(9) . . . . ? O18 C17 O19 C20 0.24(16) . . . . ? C12 C17 O19 C20 179.49(9) . . . . ? 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 N11 H11 O16 0.886(14) 2.212(15) 3.0535(12) 158.5(13) 1_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.455 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.045 _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 0.0455529 _diffrn_orient_matrix_UB_12 0.0451810 _diffrn_orient_matrix_UB_13 -0.0147723 _diffrn_orient_matrix_UB_21 0.0164712 _diffrn_orient_matrix_UB_22 -0.0078811 _diffrn_orient_matrix_UB_23 -0.1186722 _diffrn_orient_matrix_UB_31 -0.1368522 _diffrn_orient_matrix_UB_32 0.0140764 _diffrn_orient_matrix_UB_33 -0.0192614 _symmetry_space_group_name_Hall '-P 2ybc' _exptl_crystal_id 'Doyle/XuX XU-OX-N1 150K' _diffrn_measurement_details 610,610,610,1007 _diffrn_measurement_specimen_support 'MiTeGen loop' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker Smart Apex II' _diffrn_standards_decay_% 0 #_______________________________________________________________________________ # _publ_section_references ; Bruker (2010). Apex2. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Spek, A. L. (1990). Acta Cryst., A46, C-34. ;