data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jonathan White' 'Nathan Fifer' _publ_contact_author_name 'Dr Jonathan White' _publ_contact_author_address ; School of Chemistry and BIO-21 Institute University of Melbourne 30 Flemington Road Parkville Melbourne Vic 3150 AUSTRALIA ; _publ_contact_author_email WHITEJM@UNIMELB.EDU.AU _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Determining the s-Donor Ability of the Cyclopropane C-C bond. ; data_jmwnf3 _database_code_depnum_ccdc_archive 'CCDC 265209' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N O4' _chemical_formula_weight 261.27 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.9505(8) _cell_length_b 28.848(3) _cell_length_c 7.3706(8) _cell_angle_alpha 90.00 _cell_angle_beta 116.961(2) _cell_angle_gamma 90.00 _cell_volume 1317.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2258 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 6862 _diffrn_reflns_av_R_equivalents 0.0737 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2321 _reflns_number_gt 1886 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0464P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0010(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2321 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1006 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.5198(2) 0.09902(5) 0.8654(2) 0.0296(4) Uani 1 1 d . . . H1 H 0.5437 0.1037 0.7427 0.036 Uiso 1 1 calc R . . C2 C 0.7294(2) 0.08625(5) 1.0422(2) 0.0328(4) Uani 1 1 d . . . H2 H 0.7302 0.0866 1.1782 0.039 Uiso 1 1 calc R . . C3 C 0.8617(3) 0.04890(6) 1.0115(3) 0.0455(5) Uani 1 1 d . . . H3A H 0.9369 0.0267 1.1242 0.055 Uiso 1 1 calc R . . H3B H 0.8085 0.0356 0.8733 0.055 Uiso 1 1 calc R . . C4 C 0.9404(3) 0.09792(6) 1.0428(3) 0.0452(5) Uani 1 1 d . . . H4A H 0.9356 0.1148 0.9240 0.054 Uiso 1 1 calc R . . H4B H 1.0640 0.1059 1.1749 0.054 Uiso 1 1 calc R . . C5 C 0.3452(3) 0.06370(5) 0.8173(3) 0.0371(4) Uani 1 1 d . . . H5 H 0.3277 0.0515 0.9360 0.045 Uiso 1 1 calc R . . C6 C 0.3029(3) 0.02978(7) 0.6492(3) 0.0556(5) Uani 1 1 d . . . H6A H 0.3902 0.0326 0.5745 0.067 Uiso 1 1 calc R . . H6B H 0.2641 -0.0023 0.6667 0.067 Uiso 1 1 calc R . . C7 C 0.1430(3) 0.06731(7) 0.6207(3) 0.0539(5) Uani 1 1 d . . . H7A H 0.1315 0.0932 0.5284 0.065 Uiso 1 1 calc R . . H7B H 0.0054 0.0583 0.6205 0.065 Uiso 1 1 calc R . . C8 C 0.5072(2) 0.18247(5) 0.8728(2) 0.0257(4) Uani 1 1 d . . . C9 C 0.3794(2) 0.22269(5) 0.88724(19) 0.0243(3) Uani 1 1 d . . . C10 C 0.1929(2) 0.21705(5) 0.9115(2) 0.0264(4) Uani 1 1 d . . . H10 H 0.1454 0.1868 0.9230 0.032 Uiso 1 1 calc R . . C11 C 0.0769(2) 0.25542(5) 0.9190(2) 0.0280(4) Uani 1 1 d . . . H11 H -0.0512 0.2519 0.9337 0.034 Uiso 1 1 calc R . . C12 C 0.1520(2) 0.29884(5) 0.9044(2) 0.0251(3) Uani 1 1 d . . . C13 C 0.3362(2) 0.30565(5) 0.8809(2) 0.0277(4) Uani 1 1 d . . . H13 H 0.3840 0.3360 0.8719 0.033 Uiso 1 1 calc R . . C14 C 0.4490(2) 0.26712(5) 0.8709(2) 0.0273(4) Uani 1 1 d . . . H14 H 0.5750 0.2709 0.8526 0.033 Uiso 1 1 calc R . . N1 N 0.0287(2) 0.33975(5) 0.91144(18) 0.0315(3) Uani 1 1 d . . . O1 O 0.43325(15) 0.14225(3) 0.90706(16) 0.0307(3) Uani 1 1 d . . . O2 O 0.65645(16) 0.18626(3) 0.83178(16) 0.0321(3) Uani 1 1 d . . . O3 O 0.11526(18) 0.37795(4) 0.93646(18) 0.0423(3) Uani 1 1 d . . . O4 O -0.15389(17) 0.33389(4) 0.89342(17) 0.0419(3) 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 0.0380(9) 0.0219(8) 0.0351(9) -0.0009(7) 0.0219(7) 0.0007(7) C2 0.0387(9) 0.0274(9) 0.0361(9) -0.0009(7) 0.0201(8) 0.0032(7) C3 0.0474(10) 0.0351(10) 0.0581(12) -0.0017(8) 0.0277(9) 0.0077(8) C4 0.0379(10) 0.0409(11) 0.0557(11) -0.0011(9) 0.0203(9) 0.0001(8) C5 0.0426(9) 0.0296(9) 0.0413(9) -0.0006(7) 0.0208(8) -0.0067(7) C6 0.0636(12) 0.0408(11) 0.0630(13) -0.0161(9) 0.0292(11) -0.0183(10) C7 0.0441(11) 0.0548(13) 0.0554(12) -0.0041(10) 0.0161(10) -0.0122(9) C8 0.0288(8) 0.0259(9) 0.0210(8) -0.0005(6) 0.0101(7) -0.0032(6) C9 0.0257(8) 0.0264(8) 0.0177(7) 0.0005(6) 0.0071(6) 0.0000(6) C10 0.0278(8) 0.0261(9) 0.0244(8) 0.0009(6) 0.0110(6) -0.0028(6) C11 0.0254(8) 0.0316(9) 0.0268(8) 0.0018(7) 0.0118(7) -0.0001(6) C12 0.0282(8) 0.0245(8) 0.0208(7) 0.0004(6) 0.0095(6) 0.0030(6) C13 0.0320(8) 0.0225(8) 0.0282(8) 0.0008(6) 0.0132(7) -0.0029(6) C14 0.0269(8) 0.0292(9) 0.0269(8) 0.0007(6) 0.0129(6) -0.0018(6) N1 0.0370(8) 0.0318(8) 0.0268(7) 0.0025(6) 0.0154(6) 0.0028(6) O1 0.0350(6) 0.0225(6) 0.0403(6) 0.0016(5) 0.0220(5) 0.0006(4) O2 0.0366(6) 0.0282(6) 0.0393(7) -0.0011(5) 0.0241(5) -0.0013(5) O3 0.0598(8) 0.0256(7) 0.0554(8) -0.0011(5) 0.0384(6) -0.0004(6) O4 0.0308(6) 0.0425(8) 0.0524(8) 0.0002(6) 0.0188(6) 0.0068(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 O1 1.4762(17) . ? C1 C2 1.495(2) . ? C1 C5 1.499(2) . ? C2 C3 1.499(2) . ? C2 C4 1.503(2) . ? C3 C4 1.496(2) . ? C5 C7 1.496(2) . ? C5 C6 1.500(2) . ? C6 C7 1.497(3) . ? C8 O2 1.2097(17) . ? C8 O1 1.3386(16) . ? C8 C9 1.494(2) . ? C9 C14 1.3946(19) . ? C9 C10 1.3959(19) . ? C10 C11 1.385(2) . ? C11 C12 1.380(2) . ? C12 C13 1.381(2) . ? C12 N1 1.4734(19) . ? C13 C14 1.382(2) . ? N1 O4 1.2261(16) . ? N1 O3 1.2289(16) . ? 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 O1 C1 C2 110.79(12) . . ? O1 C1 C5 105.12(11) . . ? C2 C1 C5 113.77(13) . . ? C1 C2 C3 117.90(13) . . ? C1 C2 C4 120.76(14) . . ? C3 C2 C4 59.77(11) . . ? C4 C3 C2 60.24(11) . . ? C3 C4 C2 59.98(11) . . ? C7 C5 C1 119.09(15) . . ? C7 C5 C6 59.96(12) . . ? C1 C5 C6 118.25(14) . . ? C7 C6 C5 59.90(11) . . ? C5 C7 C6 60.14(11) . . ? O2 C8 O1 124.86(13) . . ? O2 C8 C9 123.55(13) . . ? O1 C8 C9 111.58(12) . . ? C14 C9 C10 119.82(13) . . ? C14 C9 C8 117.79(13) . . ? C10 C9 C8 122.37(13) . . ? C11 C10 C9 120.19(14) . . ? C12 C11 C10 118.35(13) . . ? C11 C12 C13 122.94(14) . . ? C11 C12 N1 118.52(13) . . ? C13 C12 N1 118.53(13) . . ? C12 C13 C14 118.24(14) . . ? C13 C14 C9 120.45(13) . . ? O4 N1 O3 123.51(13) . . ? O4 N1 C12 118.43(13) . . ? O3 N1 C12 118.05(12) . . ? C8 O1 C1 117.73(11) . . ? 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 O1 C1 C2 C3 -168.08(13) . . . . ? C5 C1 C2 C3 73.75(18) . . . . ? O1 C1 C2 C4 -98.43(16) . . . . ? C5 C1 C2 C4 143.40(15) . . . . ? C1 C2 C3 C4 111.18(16) . . . . ? C1 C2 C4 C3 -106.46(16) . . . . ? O1 C1 C5 C7 70.85(18) . . . . ? C2 C1 C5 C7 -167.77(15) . . . . ? O1 C1 C5 C6 140.28(14) . . . . ? C2 C1 C5 C6 -98.35(18) . . . . ? C1 C5 C6 C7 -109.07(17) . . . . ? C1 C5 C7 C6 107.69(17) . . . . ? O2 C8 C9 C14 -6.1(2) . . . . ? O1 C8 C9 C14 175.04(12) . . . . ? O2 C8 C9 C10 172.44(13) . . . . ? O1 C8 C9 C10 -6.45(18) . . . . ? C14 C9 C10 C11 0.1(2) . . . . ? C8 C9 C10 C11 -178.35(12) . . . . ? C9 C10 C11 C12 -0.8(2) . . . . ? C10 C11 C12 C13 0.6(2) . . . . ? C10 C11 C12 N1 179.77(12) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? N1 C12 C13 C14 -178.89(12) . . . . ? C12 C13 C14 C9 -1.0(2) . . . . ? C10 C9 C14 C13 0.8(2) . . . . ? C8 C9 C14 C13 179.33(12) . . . . ? C11 C12 N1 O4 -12.80(19) . . . . ? C13 C12 N1 O4 166.39(13) . . . . ? C11 C12 N1 O3 166.73(13) . . . . ? C13 C12 N1 O3 -14.07(19) . . . . ? O2 C8 O1 C1 -8.6(2) . . . . ? C9 C8 O1 C1 170.27(10) . . . . ? C2 C1 O1 C8 83.57(15) . . . . ? C5 C1 O1 C8 -153.12(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.230 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.037 data_jmwnf16 _database_code_depnum_ccdc_archive 'CCDC 265210' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 N2 O5 S' _chemical_formula_weight 270.26 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' S S 0.1246 0.1234 '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 'P2(1)/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 5.1517(14) _cell_length_b 11.726(3) _cell_length_c 18.705(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.289(5) _cell_angle_gamma 90.00 _cell_volume 1126.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1017 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 23.93 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 5769 _diffrn_reflns_av_R_equivalents 0.0887 _diffrn_reflns_av_sigmaI/netI 0.0753 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1981 _reflns_number_gt 1502 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0352P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0003(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1981 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 S1 S 0.78435(16) 0.99794(6) 0.91125(4) 0.0284(3) Uani 1 1 d . . . O2 O 0.9972(4) 0.82104(18) 0.96103(12) 0.0361(6) Uani 1 1 d . . . O3 O 0.9605(4) 0.64316(18) 0.93008(11) 0.0341(6) Uani 1 1 d . . . N1 N 0.8865(5) 0.7422(2) 0.92679(13) 0.0262(6) Uani 1 1 d . . . O5 O 0.2122(4) 0.52363(17) 0.78018(11) 0.0345(6) Uani 1 1 d . . . O4 O -0.0674(4) 0.64904(18) 0.73891(12) 0.0364(6) Uani 1 1 d . . . N2 N 0.1365(5) 0.6223(2) 0.77158(13) 0.0266(7) Uani 1 1 d . . . C8 C 0.3020(6) 0.7132(2) 0.80400(15) 0.0219(7) Uani 1 1 d . . . C7 C 0.5146(6) 0.6856(2) 0.84803(14) 0.0206(7) Uani 1 1 d . . . H10 H 0.5609 0.6098 0.8560 0.025 Uiso 1 1 calc R . . O1 O 0.6478(4) 1.11009(16) 0.87189(11) 0.0295(6) Uani 1 1 d . . . C5 C 0.5963(6) 0.8890(2) 0.87007(16) 0.0233(7) Uani 1 1 d . . . C10 C 0.3792(6) 0.9127(2) 0.82351(15) 0.0235(7) Uani 1 1 d . . . H6 H 0.3336 0.9883 0.8141 0.028 Uiso 1 1 calc R . . C9 C 0.2309(6) 0.8274(2) 0.79116(15) 0.0242(7) Uani 1 1 d . . . H5 H 0.0846 0.8450 0.7610 0.029 Uiso 1 1 calc R . . C6 C 0.6610(6) 0.7727(2) 0.88073(15) 0.0206(7) Uani 1 1 d . . . C1 C 0.4759(6) 1.1752(2) 0.91568(17) 0.0295(8) Uani 1 1 d . . . H1A H 0.5507 1.1800 0.9647 0.035 Uiso 1 1 calc R . . H1B H 0.3076 1.1381 0.9157 0.035 Uiso 1 1 calc R . . C2 C 0.4465(6) 1.2907(3) 0.88417(17) 0.0300(8) Uani 1 1 d . . . H2A H 0.3369 1.2959 0.8392 0.036 Uiso 1 1 calc R . . C4 C 0.6675(7) 1.3717(3) 0.89204(17) 0.0337(9) Uani 1 1 d . . . H4A H 0.6930 1.4225 0.8522 0.040 Uiso 1 1 calc R . . H4B H 0.8265 1.3461 0.9182 0.040 Uiso 1 1 calc R . . C3 C 0.4367(7) 1.3914(3) 0.93340(18) 0.0346(9) Uani 1 1 d . . . H3A H 0.3213 1.4538 0.9186 0.042 Uiso 1 1 calc R . . H3B H 0.4549 1.3773 0.9846 0.042 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 S1 0.0339(5) 0.0159(4) 0.0349(5) -0.0028(4) 0.0002(4) -0.0022(3) O2 0.0398(15) 0.0259(14) 0.0406(14) -0.0044(11) -0.0100(11) -0.0034(11) O3 0.0388(15) 0.0197(13) 0.0429(14) 0.0065(10) -0.0028(11) 0.0080(11) N1 0.0307(16) 0.0207(15) 0.0270(15) 0.0016(12) 0.0001(13) 0.0018(12) O5 0.0484(16) 0.0136(12) 0.0404(14) -0.0029(10) -0.0045(12) -0.0014(10) O4 0.0303(14) 0.0349(14) 0.0425(14) -0.0081(11) -0.0077(12) -0.0014(11) N2 0.0313(17) 0.0242(16) 0.0245(14) -0.0032(12) 0.0038(13) -0.0030(13) C8 0.0273(18) 0.0179(17) 0.0207(16) -0.0035(13) 0.0034(14) -0.0015(13) C7 0.0303(18) 0.0117(15) 0.0207(15) -0.0004(13) 0.0086(14) 0.0024(13) O1 0.0427(14) 0.0136(11) 0.0330(12) 0.0014(9) 0.0085(11) 0.0003(10) C5 0.0259(18) 0.0196(16) 0.0253(16) 0.0024(13) 0.0069(14) -0.0004(13) C10 0.0303(19) 0.0136(15) 0.0272(17) 0.0034(14) 0.0057(14) 0.0023(14) C9 0.0277(19) 0.0225(18) 0.0224(16) 0.0027(13) 0.0015(14) 0.0034(14) C6 0.0221(17) 0.0192(16) 0.0208(16) 0.0005(13) 0.0048(13) 0.0021(13) C1 0.032(2) 0.0216(18) 0.0351(19) -0.0040(15) 0.0047(16) -0.0029(14) C2 0.037(2) 0.0233(18) 0.0287(18) -0.0032(14) -0.0053(15) 0.0050(15) C4 0.041(2) 0.0236(18) 0.037(2) 0.0005(15) 0.0083(17) 0.0016(15) C3 0.048(2) 0.0210(18) 0.0359(19) -0.0029(15) 0.0082(17) -0.0005(16) _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 S1 O1 1.640(2) . ? S1 C5 1.747(3) . ? O2 N1 1.239(3) . ? O3 N1 1.223(3) . ? N1 C6 1.439(4) . ? O5 N2 1.227(3) . ? O4 N2 1.216(3) . ? N2 C8 1.467(4) . ? C8 C7 1.359(4) . ? C8 C9 1.404(4) . ? C7 C6 1.385(4) . ? C7 H10 0.9300 . ? O1 C1 1.465(3) . ? C5 C10 1.393(4) . ? C5 C6 1.415(4) . ? C10 C9 1.372(4) . ? C10 H6 0.9300 . ? C9 H5 0.9300 . ? C1 C2 1.480(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C4 1.482(4) . ? C2 C3 1.501(4) . ? C2 H2A 0.9800 . ? C4 C3 1.484(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? 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 O1 S1 C5 100.55(13) . . ? O3 N1 O2 123.6(3) . . ? O3 N1 C6 120.1(3) . . ? O2 N1 C6 116.4(2) . . ? O4 N2 O5 124.2(3) . . ? O4 N2 C8 118.3(3) . . ? O5 N2 C8 117.5(3) . . ? C7 C8 C9 121.2(3) . . ? C7 C8 N2 119.6(3) . . ? C9 C8 N2 119.1(3) . . ? C8 C7 C6 118.7(3) . . ? C8 C7 H10 120.7 . . ? C6 C7 H10 120.7 . . ? C1 O1 S1 115.08(18) . . ? C10 C5 C6 116.8(3) . . ? C10 C5 S1 121.5(2) . . ? C6 C5 S1 121.7(2) . . ? C9 C10 C5 121.6(3) . . ? C9 C10 H6 119.2 . . ? C5 C10 H6 119.2 . . ? C10 C9 C8 119.4(3) . . ? C10 C9 H5 120.3 . . ? C8 C9 H5 120.3 . . ? C7 C6 C5 122.3(3) . . ? C7 C6 N1 118.0(3) . . ? C5 C6 N1 119.7(3) . . ? O1 C1 C2 107.6(2) . . ? O1 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? O1 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? C1 C2 C4 119.5(3) . . ? C1 C2 C3 118.9(3) . . ? C4 C2 C3 59.7(2) . . ? C1 C2 H2A 115.7 . . ? C4 C2 H2A 115.7 . . ? C3 C2 H2A 115.7 . . ? C2 C4 C3 60.8(2) . . ? C2 C4 H4A 117.7 . . ? C3 C4 H4A 117.7 . . ? C2 C4 H4B 117.7 . . ? C3 C4 H4B 117.7 . . ? H4A C4 H4B 114.8 . . ? C4 C3 C2 59.5(2) . . ? C4 C3 H3A 117.8 . . ? C2 C3 H3A 117.8 . . ? C4 C3 H3B 117.8 . . ? C2 C3 H3B 117.8 . . ? H3A C3 H3B 115.0 . . ? 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 O4 N2 C8 C7 172.0(3) . . . . ? O5 N2 C8 C7 -7.0(4) . . . . ? O4 N2 C8 C9 -5.4(4) . . . . ? O5 N2 C8 C9 175.6(3) . . . . ? C9 C8 C7 C6 0.4(4) . . . . ? N2 C8 C7 C6 -177.0(2) . . . . ? C5 S1 O1 C1 103.7(2) . . . . ? O1 S1 C5 C10 -5.8(3) . . . . ? O1 S1 C5 C6 172.4(2) . . . . ? C6 C5 C10 C9 1.8(4) . . . . ? S1 C5 C10 C9 -179.9(2) . . . . ? C5 C10 C9 C8 -1.3(4) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? N2 C8 C9 C10 177.5(3) . . . . ? C8 C7 C6 C5 0.2(4) . . . . ? C8 C7 C6 N1 -179.6(2) . . . . ? C10 C5 C6 C7 -1.3(4) . . . . ? S1 C5 C6 C7 -179.6(2) . . . . ? C10 C5 C6 N1 178.5(2) . . . . ? S1 C5 C6 N1 0.3(4) . . . . ? O3 N1 C6 C7 8.0(4) . . . . ? O2 N1 C6 C7 -172.7(3) . . . . ? O3 N1 C6 C5 -171.9(3) . . . . ? O2 N1 C6 C5 7.5(4) . . . . ? S1 O1 C1 C2 160.2(2) . . . . ? O1 C1 C2 C4 -72.4(3) . . . . ? O1 C1 C2 C3 -141.9(3) . . . . ? C1 C2 C4 C3 -108.2(3) . . . . ? C1 C2 C3 C4 109.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.267 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.065 data_jmwnf18 _database_code_depnum_ccdc_archive 'CCDC 265211' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 N2 O6' _chemical_formula_weight 266.21 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 'Pna2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 10.1620(8) _cell_length_b 21.4665(17) _cell_length_c 5.4350(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1185.60(16) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3397 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.37 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'Bruker SAINT' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 7145 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2625 _reflns_number_gt 2532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0548P)^2^+0.0122P] 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 SHELXL _refine_ls_extinction_coef 0.0001(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.3(9) _refine_ls_number_reflns 2625 _refine_ls_number_parameters 173 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0924 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.93715(19) 0.28100(7) 0.1436(4) 0.0294(4) Uani 1 1 d . . . H1A H 1.0291 0.2888 0.1071 0.035 Uiso 1 1 calc R . . H1B H 0.8917 0.2725 -0.0097 0.035 Uiso 1 1 calc R . . C2 C 0.92473(17) 0.22664(7) 0.3128(4) 0.0293(4) Uani 1 1 d . . . H2 H 0.8352 0.2118 0.3456 0.035 Uiso 1 1 calc R . . C3 C 1.03008(19) 0.17760(8) 0.2958(4) 0.0322(4) Uani 1 1 d . . . H3A H 1.0038 0.1344 0.3151 0.039 Uiso 1 1 calc R . . H3B H 1.1016 0.1845 0.1809 0.039 Uiso 1 1 calc R . . C4 C 1.0222(2) 0.21890(8) 0.5162(4) 0.0351(4) Uani 1 1 d . . . H4A H 1.0893 0.2507 0.5350 0.042 Uiso 1 1 calc R . . H4B H 0.9915 0.2007 0.6691 0.042 Uiso 1 1 calc R . . C5 C 0.89516(15) 0.38903(7) 0.1450(3) 0.0204(3) Uani 1 1 d . . . C6 C 0.83562(15) 0.44289(7) 0.2806(3) 0.0192(3) Uani 1 1 d . . . C7 C 0.85422(15) 0.50208(7) 0.1826(3) 0.0190(3) Uani 1 1 d . . . H7 H 0.9052 0.5078 0.0423 0.023 Uiso 1 1 calc R . . C8 C 0.79524(15) 0.55244(7) 0.2983(3) 0.0198(3) Uani 1 1 d . . . C9 C 0.71908(15) 0.54647(7) 0.5065(3) 0.0187(3) Uani 1 1 d . . . H9 H 0.6808 0.5808 0.5824 0.022 Uiso 1 1 calc R . . C10 C 0.70241(15) 0.48659(7) 0.5970(3) 0.0185(3) Uani 1 1 d . . . C11 C 0.75905(15) 0.43452(7) 0.4907(3) 0.0191(3) Uani 1 1 d . . . H11 H 0.7464 0.3951 0.5575 0.023 Uiso 1 1 calc R . . N1 N 0.80808(14) 0.61478(6) 0.1858(3) 0.0233(3) Uani 1 1 d . . . N2 N 0.61706(13) 0.47803(6) 0.8132(2) 0.0203(3) Uani 1 1 d . . . O1 O 0.87913(12) 0.33552(5) 0.2636(2) 0.0250(3) Uani 1 1 d . . . O2 O 0.94919(12) 0.39482(5) -0.0520(2) 0.0287(3) Uani 1 1 d . . . O3 O 0.85677(13) 0.61790(5) -0.0199(2) 0.0306(3) Uani 1 1 d . . . O4 O 0.76687(13) 0.65935(5) 0.3022(2) 0.0324(3) Uani 1 1 d . . . O5 O 0.58968(12) 0.42486(5) 0.8757(3) 0.0300(3) Uani 1 1 d . . . O6 O 0.57882(12) 0.52496(5) 0.9209(2) 0.0252(3) 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 0.0335(10) 0.0203(9) 0.0344(11) -0.0053(8) 0.0079(8) 0.0048(6) C2 0.0259(9) 0.0195(8) 0.0425(11) -0.0055(8) 0.0051(8) -0.0003(6) C3 0.0320(9) 0.0216(8) 0.0431(12) -0.0071(9) -0.0024(9) 0.0032(7) C4 0.0462(12) 0.0230(9) 0.0362(10) -0.0054(8) 0.0001(9) -0.0017(8) C5 0.0158(7) 0.0222(8) 0.0233(8) -0.0015(7) 0.0011(7) -0.0005(6) C6 0.0161(7) 0.0195(8) 0.0220(8) -0.0008(6) -0.0032(7) -0.0009(6) C7 0.0158(7) 0.0226(8) 0.0186(7) 0.0021(7) -0.0002(6) -0.0018(6) C8 0.0172(7) 0.0190(8) 0.0232(8) 0.0038(7) -0.0047(7) -0.0020(5) C9 0.0159(7) 0.0196(8) 0.0206(7) -0.0018(7) -0.0023(6) 0.0008(5) C10 0.0159(8) 0.0229(8) 0.0166(7) 0.0007(7) -0.0020(6) -0.0015(6) C11 0.0183(7) 0.0187(7) 0.0204(7) 0.0018(6) -0.0018(7) -0.0017(6) N1 0.0213(7) 0.0206(7) 0.0278(8) 0.0062(6) -0.0037(6) -0.0019(5) N2 0.0185(7) 0.0253(7) 0.0170(7) 0.0020(6) -0.0009(6) -0.0001(5) O1 0.0280(6) 0.0188(6) 0.0281(6) -0.0005(5) 0.0064(5) 0.0026(4) O2 0.0308(6) 0.0274(6) 0.0278(7) -0.0002(5) 0.0072(6) 0.0018(5) O3 0.0364(7) 0.0285(6) 0.0270(6) 0.0088(6) 0.0028(6) -0.0040(5) O4 0.0370(7) 0.0192(6) 0.0408(8) 0.0035(6) 0.0050(6) 0.0056(5) O5 0.0348(7) 0.0253(6) 0.0300(7) 0.0067(5) 0.0094(6) -0.0015(5) O6 0.0231(6) 0.0289(6) 0.0236(6) -0.0040(5) 0.0026(5) 0.0019(4) _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 O1 1.4640(19) . ? C1 C2 1.491(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C4 1.494(3) . ? C2 C3 1.504(2) . ? C2 H2 0.9800 . ? C3 C4 1.492(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O2 1.209(2) . ? C5 O1 1.3274(19) . ? C5 C6 1.499(2) . ? C6 C7 1.390(2) . ? C6 C11 1.393(2) . ? C7 C8 1.387(2) . ? C7 H7 0.9300 . ? C8 C9 1.377(2) . ? C8 N1 1.477(2) . ? C9 C10 1.387(2) . ? C9 H9 0.9300 . ? C10 C11 1.384(2) . ? C10 N2 1.472(2) . ? C11 H11 0.9300 . ? N1 O4 1.2210(18) . ? N1 O3 1.2245(19) . ? N2 O5 1.2228(17) . ? N2 O6 1.2282(17) . ? 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 O1 C1 C2 108.46(15) . . ? O1 C1 H1A 110.0 . . ? C2 C1 H1A 110.0 . . ? O1 C1 H1B 110.0 . . ? C2 C1 H1B 110.0 . . ? H1A C1 H1B 108.4 . . ? C1 C2 C4 119.16(15) . . ? C1 C2 C3 116.72(16) . . ? C4 C2 C3 59.71(12) . . ? C1 C2 H2 116.4 . . ? C4 C2 H2 116.4 . . ? C3 C2 H2 116.4 . . ? C4 C3 C2 59.80(13) . . ? C4 C3 H3A 117.8 . . ? C2 C3 H3A 117.8 . . ? C4 C3 H3B 117.8 . . ? C2 C3 H3B 117.8 . . ? H3A C3 H3B 114.9 . . ? C3 C4 C2 60.49(13) . . ? C3 C4 H4A 117.7 . . ? C2 C4 H4A 117.7 . . ? C3 C4 H4B 117.7 . . ? C2 C4 H4B 117.7 . . ? H4A C4 H4B 114.8 . . ? O2 C5 O1 125.08(15) . . ? O2 C5 C6 122.63(15) . . ? O1 C5 C6 112.28(14) . . ? C7 C6 C11 120.49(15) . . ? C7 C6 C5 117.50(15) . . ? C11 C6 C5 121.94(14) . . ? C8 C7 C6 118.69(15) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C9 C8 C7 122.88(14) . . ? C9 C8 N1 118.29(14) . . ? C7 C8 N1 118.73(15) . . ? C8 C9 C10 116.52(14) . . ? C8 C9 H9 121.7 . . ? C10 C9 H9 121.7 . . ? C11 C10 C9 123.34(15) . . ? C11 C10 N2 118.53(14) . . ? C9 C10 N2 118.10(13) . . ? C10 C11 C6 118.07(15) . . ? C10 C11 H11 121.0 . . ? C6 C11 H11 121.0 . . ? O4 N1 O3 124.66(14) . . ? O4 N1 C8 117.74(14) . . ? O3 N1 C8 117.58(14) . . ? O5 N2 O6 124.13(14) . . ? O5 N2 C10 118.20(13) . . ? O6 N2 C10 117.67(12) . . ? C5 O1 C1 115.21(13) . . ? 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 O1 C1 C2 C4 -81.1(2) . . . . ? O1 C1 C2 C3 -149.64(16) . . . . ? C1 C2 C3 C4 109.74(18) . . . . ? C1 C2 C4 C3 -105.68(19) . . . . ? O2 C5 C6 C7 -5.6(2) . . . . ? O1 C5 C6 C7 175.61(14) . . . . ? O2 C5 C6 C11 171.49(16) . . . . ? O1 C5 C6 C11 -7.4(2) . . . . ? C11 C6 C7 C8 0.1(2) . . . . ? C5 C6 C7 C8 177.15(14) . . . . ? C6 C7 C8 C9 0.1(2) . . . . ? C6 C7 C8 N1 -176.26(13) . . . . ? C7 C8 C9 C10 -0.5(2) . . . . ? N1 C8 C9 C10 175.87(14) . . . . ? C8 C9 C10 C11 0.8(2) . . . . ? C8 C9 C10 N2 -177.46(13) . . . . ? C9 C10 C11 C6 -0.6(2) . . . . ? N2 C10 C11 C6 177.60(13) . . . . ? C7 C6 C11 C10 0.2(2) . . . . ? C5 C6 C11 C10 -176.77(14) . . . . ? C9 C8 N1 O4 10.5(2) . . . . ? C7 C8 N1 O4 -172.91(15) . . . . ? C9 C8 N1 O3 -167.91(14) . . . . ? C7 C8 N1 O3 8.6(2) . . . . ? C11 C10 N2 O5 -6.8(2) . . . . ? C9 C10 N2 O5 171.50(14) . . . . ? C11 C10 N2 O6 172.50(15) . . . . ? C9 C10 N2 O6 -9.2(2) . . . . ? O2 C5 O1 C1 2.3(2) . . . . ? C6 C5 O1 C1 -178.91(14) . . . . ? C2 C1 O1 C5 173.33(14) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.252 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.043 data_jmwnf23 _database_code_depnum_ccdc_archive 'CCDC 265212' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 N O4' _chemical_formula_weight 221.21 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 'P2(1)/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 11.503(2) _cell_length_b 7.7574(16) _cell_length_c 12.737(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.040(4) _cell_angle_gamma 90.00 _cell_volume 1060.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1037 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 25.08 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 4383 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1833 _reflns_number_gt 1267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0345P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0002(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1833 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _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 0.5526(2) 0.7370(3) 0.4411(2) 0.0406(6) Uani 1 1 d . . . H1A H 0.5840 0.8409 0.4182 0.049 Uiso 1 1 calc R . . H1B H 0.5273 0.7653 0.5040 0.049 Uiso 1 1 calc R . . C2 C 0.44409(19) 0.6703(3) 0.34599(19) 0.0324(6) Uani 1 1 d . . . H2 H 0.4066 0.5637 0.3603 0.039 Uiso 1 1 calc R . . C3 C 0.3559(2) 0.7994(3) 0.2712(2) 0.0437(7) Uani 1 1 d . . . H3A H 0.2678 0.7717 0.2430 0.052 Uiso 1 1 calc R . . H3B H 0.3751 0.9207 0.2868 0.052 Uiso 1 1 calc R . . C4 C 0.4388(2) 0.6965(3) 0.2283(2) 0.0431(6) Uani 1 1 d . . . H4A H 0.5081 0.7553 0.2177 0.052 Uiso 1 1 calc R . . H4B H 0.4009 0.6064 0.1740 0.052 Uiso 1 1 calc R . . C5 C 0.76580(19) 0.6606(3) 0.53222(17) 0.0279(5) Uani 1 1 d . . . C6 C 0.85695(19) 0.5158(2) 0.56864(16) 0.0252(5) Uani 1 1 d . . . C7 C 0.98208(18) 0.5580(3) 0.62787(16) 0.0264(5) Uani 1 1 d . . . H7 H 1.0052 0.6726 0.6443 0.032 Uiso 1 1 calc R . . C8 C 1.07125(19) 0.4293(3) 0.66193(16) 0.0276(5) Uani 1 1 d . . . H8 H 1.1543 0.4562 0.7016 0.033 Uiso 1 1 calc R . . C9 C 1.03461(18) 0.2604(2) 0.63591(16) 0.0249(5) Uani 1 1 d . . . C10 C 0.91133(19) 0.2140(3) 0.57933(16) 0.0281(5) Uani 1 1 d . . . H10 H 0.8889 0.0989 0.5644 0.034 Uiso 1 1 calc R . . C11 C 0.82279(19) 0.3428(2) 0.54573(17) 0.0269(5) Uani 1 1 d . . . H11 H 0.7397 0.3143 0.5075 0.032 Uiso 1 1 calc R . . N1 N 1.13093(17) 0.1238(2) 0.66939(14) 0.0314(5) Uani 1 1 d . . . O1 O 0.64979(13) 0.60577(17) 0.47489(12) 0.0338(4) Uani 1 1 d . . . O2 O 0.79309(14) 0.81055(19) 0.55219(14) 0.0435(5) Uani 1 1 d . . . O3 O 1.09806(13) -0.02690(18) 0.64763(12) 0.0392(4) Uani 1 1 d . . . O4 O 1.24012(14) 0.16803(19) 0.71821(14) 0.0449(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 0.0355(14) 0.0341(13) 0.0472(15) 0.0022(11) 0.0087(12) 0.0106(11) C2 0.0214(12) 0.0293(12) 0.0449(15) 0.0045(11) 0.0101(11) 0.0017(10) C3 0.0240(13) 0.0321(13) 0.0641(18) 0.0057(12) 0.0024(12) 0.0034(11) C4 0.0357(14) 0.0464(15) 0.0426(15) 0.0016(12) 0.0083(12) -0.0019(12) C5 0.0289(13) 0.0311(13) 0.0229(12) -0.0019(10) 0.0085(10) -0.0055(10) C6 0.0252(12) 0.0314(12) 0.0199(11) 0.0014(10) 0.0091(9) -0.0010(10) C7 0.0269(13) 0.0284(12) 0.0239(12) -0.0031(9) 0.0093(10) -0.0067(10) C8 0.0191(11) 0.0371(13) 0.0255(12) -0.0019(10) 0.0069(10) -0.0062(10) C9 0.0231(12) 0.0306(12) 0.0224(12) 0.0031(10) 0.0098(10) 0.0006(10) C10 0.0312(13) 0.0279(12) 0.0265(13) -0.0029(10) 0.0119(11) -0.0049(10) C11 0.0211(12) 0.0320(12) 0.0268(13) 0.0002(10) 0.0078(10) -0.0050(9) N1 0.0320(12) 0.0367(11) 0.0289(11) 0.0012(9) 0.0151(9) -0.0003(9) O1 0.0248(9) 0.0293(8) 0.0416(9) 0.0005(7) 0.0051(8) 0.0017(7) O2 0.0355(10) 0.0295(9) 0.0580(11) -0.0038(8) 0.0076(8) -0.0023(7) O3 0.0415(10) 0.0300(9) 0.0468(10) 0.0014(8) 0.0166(8) 0.0021(8) O4 0.0193(9) 0.0520(10) 0.0569(11) -0.0037(9) 0.0057(8) 0.0000(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 O1 1.458(2) . ? C1 C2 1.485(3) . ? C2 C4 1.491(3) . ? C2 C3 1.498(3) . ? C3 C4 1.490(3) . ? C5 O2 1.208(2) . ? C5 O1 1.340(2) . ? C5 C6 1.493(3) . ? C6 C11 1.399(3) . ? C6 C7 1.403(3) . ? C7 C8 1.385(3) . ? C8 C9 1.380(3) . ? C9 C10 1.388(3) . ? C9 N1 1.481(3) . ? C10 C11 1.380(3) . ? N1 O3 1.229(2) . ? N1 O4 1.233(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 O1 C1 C2 109.18(17) . . ? C1 C2 C4 119.4(2) . . ? C1 C2 C3 117.66(18) . . ? C4 C2 C3 59.78(14) . . ? C4 C3 C2 59.88(14) . . ? C3 C4 C2 60.33(15) . . ? O2 C5 O1 123.60(19) . . ? O2 C5 C6 124.00(19) . . ? O1 C5 C6 112.40(17) . . ? C11 C6 C7 119.55(19) . . ? C11 C6 C5 122.95(19) . . ? C7 C6 C5 117.50(18) . . ? C8 C7 C6 120.11(19) . . ? C9 C8 C7 118.77(19) . . ? C8 C9 C10 122.54(19) . . ? C8 C9 N1 118.55(18) . . ? C10 C9 N1 118.92(18) . . ? C11 C10 C9 118.43(18) . . ? C10 C11 C6 120.58(19) . . ? O3 N1 O4 123.61(18) . . ? O3 N1 C9 118.53(18) . . ? O4 N1 C9 117.86(17) . . ? C5 O1 C1 116.57(16) . . ? 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 O1 C1 C2 C4 -88.6(2) . . . . ? O1 C1 C2 C3 -157.74(19) . . . . ? C1 C2 C3 C4 109.7(2) . . . . ? C1 C2 C4 C3 -106.8(2) . . . . ? O2 C5 C6 C11 179.2(2) . . . . ? O1 C5 C6 C11 -0.7(3) . . . . ? O2 C5 C6 C7 -1.2(3) . . . . ? O1 C5 C6 C7 178.94(16) . . . . ? C11 C6 C7 C8 0.9(3) . . . . ? C5 C6 C7 C8 -178.75(18) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C10 -1.6(3) . . . . ? C7 C8 C9 N1 178.11(17) . . . . ? C8 C9 C10 C11 1.5(3) . . . . ? N1 C9 C10 C11 -178.21(17) . . . . ? C9 C10 C11 C6 -0.2(3) . . . . ? C7 C6 C11 C10 -1.0(3) . . . . ? C5 C6 C11 C10 178.63(18) . . . . ? C8 C9 N1 O3 178.98(17) . . . . ? C10 C9 N1 O3 -1.3(3) . . . . ? C8 C9 N1 O4 -0.7(3) . . . . ? C10 C9 N1 O4 179.02(17) . . . . ? O2 C5 O1 C1 -3.2(3) . . . . ? C6 C5 O1 C1 176.64(17) . . . . ? C2 C1 O1 C5 159.02(18) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.213 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.041 data_jmwnf33 _database_code_depnum_ccdc_archive 'CCDC 265213' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 N O3' _chemical_formula_weight 193.20 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/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 11.1796(17) _cell_length_b 7.2234(11) _cell_length_c 12.745(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.033(3) _cell_angle_gamma 90.00 _cell_volume 932.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1180 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 26.83 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 5551 _diffrn_reflns_av_R_equivalents 0.0798 _diffrn_reflns_av_sigmaI/netI 0.0795 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.59 _reflns_number_total 2115 _reflns_number_gt 1392 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0381P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2115 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1123 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 0.20084(14) 0.0880(2) 0.01934(14) 0.0252(4) Uani 1 1 d . . . H1A H 0.1828 0.2095 0.0418 0.030 Uiso 1 1 calc R . . H1B H 0.1799 -0.0043 0.0643 0.030 Uiso 1 1 calc R . . C2 C 0.11880(15) 0.0575(2) -0.10647(15) 0.0260(4) Uani 1 1 d . . . H2 H 0.1147 -0.0698 -0.1344 0.031 Uiso 1 1 calc R . . C3 C -0.00558(15) 0.1700(2) -0.16242(15) 0.0305(5) Uani 1 1 d . . . H3A H -0.0826 0.1104 -0.2211 0.037 Uiso 1 1 calc R . . H3B H -0.0245 0.2595 -0.1148 0.037 Uiso 1 1 calc R . . C4 C 0.10880(15) 0.2075(3) -0.19058(15) 0.0295(4) Uani 1 1 d . . . H4A H 0.1589 0.3200 -0.1601 0.035 Uiso 1 1 calc R . . H4B H 0.1010 0.1709 -0.2665 0.035 Uiso 1 1 calc R . . C5 C 0.43072(14) 0.0874(2) 0.15279(14) 0.0222(4) Uani 1 1 d . . . C6 C 0.40207(15) 0.1017(2) 0.24835(15) 0.0258(4) Uani 1 1 d . . . H6 H 0.3148 0.1052 0.2384 0.031 Uiso 1 1 calc R . . C7 C 0.50304(15) 0.1106(2) 0.35767(14) 0.0263(4) Uani 1 1 d . . . H7 H 0.4844 0.1213 0.4219 0.032 Uiso 1 1 calc R . . C8 C 0.63220(14) 0.1035(2) 0.37157(14) 0.0215(4) Uani 1 1 d . . . C9 C 0.66215(15) 0.0919(2) 0.27691(15) 0.0266(4) Uani 1 1 d . . . H9 H 0.7497 0.0899 0.2874 0.032 Uiso 1 1 calc R . . C10 C 0.56201(15) 0.0831(2) 0.16772(14) 0.0273(4) Uani 1 1 d . . . H10 H 0.5813 0.0744 0.1037 0.033 Uiso 1 1 calc R . . N N 0.73790(12) 0.10773(19) 0.48756(12) 0.0252(3) Uani 1 1 d . . . O1 O 0.33846(10) 0.07437(17) 0.04117(9) 0.0281(3) Uani 1 1 d . . . O2 O 0.70928(11) 0.11917(18) 0.57072(10) 0.0347(3) Uani 1 1 d . . . O3 O 0.85313(10) 0.09686(18) 0.49938(11) 0.0362(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 0.0199(8) 0.0322(10) 0.0232(9) 0.0007(8) 0.0089(7) 0.0013(7) C2 0.0247(9) 0.0254(10) 0.0244(9) -0.0030(7) 0.0069(7) -0.0011(7) C3 0.0212(9) 0.0402(12) 0.0254(10) -0.0038(8) 0.0053(8) 0.0021(8) C4 0.0291(9) 0.0361(11) 0.0227(9) -0.0014(8) 0.0104(8) -0.0016(8) C5 0.0221(8) 0.0221(9) 0.0217(9) -0.0007(7) 0.0087(7) -0.0010(7) C6 0.0203(8) 0.0337(10) 0.0256(9) 0.0019(8) 0.0118(7) 0.0027(8) C7 0.0246(8) 0.0365(11) 0.0210(9) 0.0015(8) 0.0128(7) 0.0016(8) C8 0.0222(8) 0.0184(9) 0.0208(9) 0.0012(7) 0.0062(7) 0.0004(7) C9 0.0206(8) 0.0305(10) 0.0311(10) -0.0035(8) 0.0131(8) -0.0027(8) C10 0.0269(9) 0.0369(11) 0.0220(9) -0.0033(8) 0.0143(8) -0.0022(8) N 0.0239(7) 0.0243(8) 0.0250(8) 0.0012(6) 0.0080(6) -0.0008(6) O1 0.0191(6) 0.0445(8) 0.0200(7) -0.0026(5) 0.0075(5) 0.0016(5) O2 0.0328(7) 0.0503(9) 0.0202(7) -0.0008(6) 0.0105(6) 0.0021(6) O3 0.0193(6) 0.0530(9) 0.0325(8) 0.0030(6) 0.0074(6) -0.0011(6) _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 O1 1.4464(17) . ? C1 C2 1.489(2) . ? C2 C4 1.495(2) . ? C2 C3 1.504(2) . ? C3 C4 1.492(2) . ? C5 O1 1.3618(18) . ? C5 C6 1.388(2) . ? C5 C10 1.398(2) . ? C6 C7 1.374(2) . ? C7 C8 1.379(2) . ? C8 C9 1.384(2) . ? C8 N 1.451(2) . ? C9 C10 1.369(2) . ? N O2 1.2326(17) . ? N O3 1.2345(16) . ? 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 O1 C1 C2 108.51(13) . . ? C1 C2 C4 119.36(15) . . ? C1 C2 C3 117.08(15) . . ? C4 C2 C3 59.67(11) . . ? C4 C3 C2 59.84(11) . . ? C3 C4 C2 60.49(11) . . ? O1 C5 C6 124.59(14) . . ? O1 C5 C10 115.34(14) . . ? C6 C5 C10 120.06(15) . . ? C7 C6 C5 119.84(14) . . ? C6 C7 C8 119.65(15) . . ? C7 C8 C9 121.09(15) . . ? C7 C8 N 119.15(15) . . ? C9 C8 N 119.76(14) . . ? C10 C9 C8 119.55(14) . . ? C9 C10 C5 119.80(15) . . ? O2 N O3 122.44(14) . . ? O2 N C8 118.80(13) . . ? O3 N C8 118.75(14) . . ? C5 O1 C1 118.03(13) . . ? 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 O1 C1 C2 C4 -74.74(18) . . . . ? O1 C1 C2 C3 -143.44(14) . . . . ? C1 C2 C3 C4 109.81(17) . . . . ? C1 C2 C4 C3 -106.02(17) . . . . ? O1 C5 C6 C7 178.76(16) . . . . ? C10 C5 C6 C7 -0.3(2) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? C6 C7 C8 C9 1.5(3) . . . . ? C6 C7 C8 N -178.26(15) . . . . ? C7 C8 C9 C10 -1.4(3) . . . . ? N C8 C9 C10 178.33(15) . . . . ? C8 C9 C10 C5 0.5(3) . . . . ? O1 C5 C10 C9 -178.76(15) . . . . ? C6 C5 C10 C9 0.4(3) . . . . ? C7 C8 N O2 -0.6(2) . . . . ? C9 C8 N O2 179.61(15) . . . . ? C7 C8 N O3 178.28(14) . . . . ? C9 C8 N O3 -1.5(2) . . . . ? C6 C5 O1 C1 4.1(2) . . . . ? C10 C5 O1 C1 -176.72(14) . . . . ? C2 C1 O1 C5 -176.28(14) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.231 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.047 data_jmwf5a _database_code_depnum_ccdc_archive 'CCDC 265214' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 N2 O6' _chemical_formula_weight 306.27 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.0459(19) _cell_length_b 7.8502(11) _cell_length_c 14.279(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.424(2) _cell_angle_gamma 90.00 _cell_volume 1422.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4933 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 28.14 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 9945 _diffrn_reflns_av_R_equivalents 0.0849 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2498 _reflns_number_gt 2155 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0505P)^2^+0.2699P] 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 SHELXL _refine_ls_extinction_coef 0.0017(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2498 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.57516(14) 0.24270(18) 0.68230(12) 0.0332(4) Uani 1 1 d . . . C2 C 0.47633(13) 0.1932(2) 0.59258(12) 0.0372(4) Uani 1 1 d . . . C3 C 0.40973(16) 0.3299(2) 0.52034(16) 0.0483(5) Uani 1 1 d . . . C4 C 0.37249(17) 0.2383(3) 0.59028(17) 0.0514(5) Uani 1 1 d . . . C5 C 0.67406(15) 0.2429(2) 0.66614(13) 0.0405(4) Uani 1 1 d . . . C6 C 0.66869(16) 0.2437(2) 0.55918(15) 0.0451(5) Uani 1 1 d . . . C7 C 0.70552(15) 0.0875(2) 0.62523(15) 0.0438(4) Uani 1 1 d . . . C8 C 0.56566(12) 0.15587(18) 0.84055(11) 0.0286(3) Uani 1 1 d . . . C9 C 0.58256(11) 0.00743(17) 0.91218(11) 0.0267(3) Uani 1 1 d . . . C10 C 0.55482(11) -0.16108(17) 0.87933(11) 0.0265(3) Uani 1 1 d . . . C11 C 0.57980(12) -0.29657(18) 0.94715(11) 0.0275(3) Uani 1 1 d . . . C12 C 0.63193(11) -0.25889(17) 1.05141(11) 0.0272(3) Uani 1 1 d . . . C13 C 0.65925(12) -0.09508(18) 1.08850(12) 0.0297(3) Uani 1 1 d . . . C14 C 0.63470(12) 0.03714(18) 1.01821(11) 0.0293(3) Uani 1 1 d . . . N1 N 0.49130(11) -0.19789(15) 0.76885(10) 0.0358(3) Uani 1 1 d . . . N2 N 0.65891(10) -0.39940(16) 1.12676(10) 0.0329(3) Uani 1 1 d . . . O1 O 0.59367(9) 0.11491(12) 0.76573(8) 0.0341(3) Uani 1 1 d . . . O2 O 0.53681(10) 0.29364(13) 0.85491(8) 0.0390(3) Uani 1 1 d . . . O3 O 0.41493(10) -0.10745(15) 0.72215(9) 0.0462(3) Uani 1 1 d . . . O4 O 0.51825(14) -0.31770(16) 0.73122(10) 0.0665(5) Uani 1 1 d . . . O5 O 0.63811(10) -0.54516(13) 1.09350(9) 0.0452(3) Uani 1 1 d . . . O6 O 0.69972(10) -0.36253(15) 1.21866(8) 0.0450(3) Uani 1 1 d . . . H1 H 0.5705(13) 0.352(2) 0.7121(13) 0.034(4) Uiso 1 1 d . . . H2 H 0.4805(15) 0.075(2) 0.5604(13) 0.048(5) Uiso 1 1 d . . . H3A H 0.3781(14) 0.306(2) 0.4480(15) 0.037(4) Uiso 1 1 d . . . H3B H 0.4335(16) 0.446(3) 0.5394(14) 0.051(5) Uiso 1 1 d . . . H4A H 0.3148(16) 0.151(2) 0.5515(14) 0.046(5) Uiso 1 1 d . . . H4B H 0.3770(16) 0.305(2) 0.6509(15) 0.051(5) Uiso 1 1 d . . . H5 H 0.7357(18) 0.298(3) 0.7198(16) 0.058(6) Uiso 1 1 d . . . H6A H 0.7213(18) 0.312(3) 0.5483(16) 0.060(6) Uiso 1 1 d . . . H6B H 0.5935(19) 0.237(2) 0.4983(16) 0.057(6) Uiso 1 1 d . . . H7A H 0.7820(18) 0.061(2) 0.6602(15) 0.062(6) Uiso 1 1 d . . . H7B H 0.6540(17) -0.012(3) 0.6084(14) 0.057(5) Uiso 1 1 d . . . H11 H 0.5610(12) -0.403(2) 0.9238(11) 0.025(4) Uiso 1 1 d . . . H13 H 0.6940(13) -0.0768(19) 1.1616(13) 0.032(4) Uiso 1 1 d . . . H14 H 0.6525(14) 0.147(2) 1.0400(12) 0.033(4) 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 0.0448(10) 0.0257(8) 0.0357(8) 0.0033(6) 0.0235(8) 0.0015(6) C2 0.0422(10) 0.0349(8) 0.0401(9) 0.0033(7) 0.0229(8) 0.0000(7) C3 0.0527(12) 0.0401(10) 0.0495(12) 0.0094(8) 0.0195(9) 0.0057(8) C4 0.0441(11) 0.0616(12) 0.0514(11) 0.0092(10) 0.0233(9) 0.0126(9) C5 0.0415(10) 0.0415(9) 0.0404(9) 0.0002(7) 0.0195(8) -0.0076(7) C6 0.0441(11) 0.0518(11) 0.0509(11) 0.0156(8) 0.0312(10) 0.0070(8) C7 0.0406(10) 0.0476(10) 0.0492(10) 0.0098(8) 0.0252(9) 0.0075(8) C8 0.0285(8) 0.0279(7) 0.0317(8) -0.0037(6) 0.0150(7) -0.0031(6) C9 0.0251(7) 0.0266(7) 0.0335(8) -0.0015(6) 0.0173(6) 0.0010(6) C10 0.0262(8) 0.0278(7) 0.0283(7) -0.0030(6) 0.0143(6) -0.0005(6) C11 0.0277(8) 0.0232(7) 0.0359(8) -0.0043(6) 0.0179(7) -0.0016(6) C12 0.0256(8) 0.0284(7) 0.0324(8) 0.0021(6) 0.0169(6) 0.0023(5) C13 0.0287(8) 0.0328(8) 0.0295(8) -0.0046(6) 0.0143(7) -0.0009(6) C14 0.0309(8) 0.0247(7) 0.0352(8) -0.0069(6) 0.0170(7) -0.0040(6) N1 0.0448(9) 0.0292(7) 0.0309(7) -0.0026(6) 0.0139(6) -0.0032(6) N2 0.0317(7) 0.0336(7) 0.0366(8) 0.0041(5) 0.0179(6) 0.0054(5) O1 0.0455(7) 0.0288(5) 0.0369(6) 0.0035(4) 0.0262(5) 0.0046(4) O2 0.0555(8) 0.0270(6) 0.0409(6) 0.0003(4) 0.0268(6) 0.0056(5) O3 0.0391(7) 0.0515(7) 0.0384(6) 0.0022(5) 0.0074(5) 0.0017(6) O4 0.1011(12) 0.0471(8) 0.0367(7) -0.0128(6) 0.0158(7) 0.0206(7) O5 0.0587(8) 0.0267(6) 0.0516(7) 0.0055(5) 0.0250(6) 0.0032(5) O6 0.0527(8) 0.0480(7) 0.0314(6) 0.0080(5) 0.0153(6) 0.0110(6) _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 1.481(2) . ? C1 O1 1.4924(17) . ? C1 C5 1.503(2) . ? C1 H1 0.974(17) . ? C2 C4 1.488(3) . ? C2 C3 1.504(2) . ? C2 H2 1.046(18) . ? C3 C4 1.495(3) . ? C3 H3A 0.951(18) . ? C3 H3B 0.97(2) . ? C4 H4A 1.03(2) . ? C4 H4B 0.99(2) . ? C5 C6 1.497(2) . ? C5 C7 1.498(2) . ? C5 H5 0.98(2) . ? C6 C7 1.497(2) . ? C6 H6A 0.98(2) . ? C6 H6B 1.04(2) . ? C7 H7A 0.99(2) . ? C7 H7B 1.02(2) . ? C8 O2 1.2031(17) . ? C8 O1 1.3268(17) . ? C8 C9 1.501(2) . ? C9 C14 1.390(2) . ? C9 C10 1.402(2) . ? C10 C11 1.379(2) . ? C10 N1 1.4695(19) . ? C11 C12 1.380(2) . ? C11 H11 0.899(15) . ? C12 C13 1.381(2) . ? C12 N2 1.4724(18) . ? C13 C14 1.381(2) . ? C13 H13 0.955(17) . ? C14 H14 0.912(17) . ? N1 O3 1.2187(17) . ? N1 O4 1.2213(18) . ? N2 O6 1.2200(17) . ? N2 O5 1.2252(16) . ? 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 O1 106.95(12) . . ? C2 C1 C5 116.90(13) . . ? O1 C1 C5 105.51(13) . . ? C2 C1 H1 113.4(10) . . ? O1 C1 H1 105.4(10) . . ? C5 C1 H1 107.8(10) . . ? C1 C2 C4 120.16(16) . . ? C1 C2 C3 118.82(15) . . ? C4 C2 C3 59.97(12) . . ? C1 C2 H2 113.8(10) . . ? C4 C2 H2 116.1(10) . . ? C3 C2 H2 117.7(10) . . ? C4 C3 C2 59.48(11) . . ? C4 C3 H3A 119.8(11) . . ? C2 C3 H3A 117.9(10) . . ? C4 C3 H3B 116.1(11) . . ? C2 C3 H3B 116.1(12) . . ? H3A C3 H3B 115.7(16) . . ? C2 C4 C3 60.56(12) . . ? C2 C4 H4A 113.1(11) . . ? C3 C4 H4A 112.5(10) . . ? C2 C4 H4B 114.4(12) . . ? C3 C4 H4B 114.7(11) . . ? H4A C4 H4B 124.6(16) . . ? C6 C5 C7 59.97(12) . . ? C6 C5 C1 120.79(16) . . ? C7 C5 C1 120.39(15) . . ? C6 C5 H5 115.9(12) . . ? C7 C5 H5 111.0(12) . . ? C1 C5 H5 116.5(12) . . ? C5 C6 C7 60.07(11) . . ? C5 C6 H6A 117.0(12) . . ? C7 C6 H6A 118.1(12) . . ? C5 C6 H6B 116.1(11) . . ? C7 C6 H6B 116.1(10) . . ? H6A C6 H6B 117.2(16) . . ? C6 C7 C5 59.96(11) . . ? C6 C7 H7A 119.6(12) . . ? C5 C7 H7A 114.2(12) . . ? C6 C7 H7B 117.4(11) . . ? C5 C7 H7B 114.6(12) . . ? H7A C7 H7B 117.6(16) . . ? O2 C8 O1 126.38(13) . . ? O2 C8 C9 123.24(13) . . ? O1 C8 C9 110.23(11) . . ? C14 C9 C10 117.63(13) . . ? C14 C9 C8 117.87(12) . . ? C10 C9 C8 124.39(13) . . ? C11 C10 C9 122.87(13) . . ? C11 C10 N1 117.16(12) . . ? C9 C10 N1 119.88(12) . . ? C10 C11 C12 116.72(13) . . ? C10 C11 H11 120.9(9) . . ? C12 C11 H11 122.3(9) . . ? C11 C12 C13 123.01(13) . . ? C11 C12 N2 118.60(12) . . ? C13 C12 N2 118.39(13) . . ? C14 C13 C12 118.67(14) . . ? C14 C13 H13 122.2(9) . . ? C12 C13 H13 119.1(9) . . ? C13 C14 C9 121.07(13) . . ? C13 C14 H14 120.9(10) . . ? C9 C14 H14 118.0(10) . . ? O3 N1 O4 125.04(13) . . ? O3 N1 C10 117.32(12) . . ? O4 N1 C10 117.63(13) . . ? O6 N2 O5 124.22(13) . . ? O6 N2 C12 117.58(12) . . ? O5 N2 C12 118.20(13) . . ? C8 O1 C1 118.01(11) . . ? 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 O1 C1 C2 C4 80.58(17) . . . . ? C5 C1 C2 C4 -161.52(15) . . . . ? O1 C1 C2 C3 150.64(14) . . . . ? C5 C1 C2 C3 -91.45(19) . . . . ? C1 C2 C3 C4 -110.14(18) . . . . ? C1 C2 C4 C3 107.94(18) . . . . ? C2 C1 C5 C6 17.3(2) . . . . ? O1 C1 C5 C6 136.03(15) . . . . ? C2 C1 C5 C7 -53.6(2) . . . . ? O1 C1 C5 C7 65.05(19) . . . . ? C1 C5 C6 C7 -109.62(18) . . . . ? C1 C5 C7 C6 110.27(19) . . . . ? O2 C8 C9 C14 -43.7(2) . . . . ? O1 C8 C9 C14 132.14(13) . . . . ? O2 C8 C9 C10 140.20(15) . . . . ? O1 C8 C9 C10 -43.94(19) . . . . ? C14 C9 C10 C11 -2.0(2) . . . . ? C8 C9 C10 C11 174.12(13) . . . . ? C14 C9 C10 N1 174.51(13) . . . . ? C8 C9 C10 N1 -9.4(2) . . . . ? C9 C10 C11 C12 1.7(2) . . . . ? N1 C10 C11 C12 -174.82(13) . . . . ? C10 C11 C12 C13 -0.3(2) . . . . ? C10 C11 C12 N2 179.18(12) . . . . ? C11 C12 C13 C14 -0.9(2) . . . . ? N2 C12 C13 C14 179.63(13) . . . . ? C12 C13 C14 C9 0.7(2) . . . . ? C10 C9 C14 C13 0.7(2) . . . . ? C8 C9 C14 C13 -175.66(13) . . . . ? C11 C10 N1 O3 131.43(14) . . . . ? C9 C10 N1 O3 -45.2(2) . . . . ? C11 C10 N1 O4 -47.7(2) . . . . ? C9 C10 N1 O4 135.60(15) . . . . ? C11 C12 N2 O6 -176.03(13) . . . . ? C13 C12 N2 O6 3.4(2) . . . . ? C11 C12 N2 O5 3.2(2) . . . . ? C13 C12 N2 O5 -177.31(13) . . . . ? O2 C8 O1 C1 -8.6(2) . . . . ? C9 C8 O1 C1 175.66(12) . . . . ? C2 C1 O1 C8 -98.96(15) . . . . ? C5 C1 O1 C8 135.91(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.278 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.041 data_jmwnf20 _database_code_depnum_ccdc_archive 'CCDC 265215' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N2 O5 S' _chemical_formula_weight 310.32 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/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 10.3778(8) _cell_length_b 12.0317(10) _cell_length_c 11.3503(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.395(2) _cell_angle_gamma 90.00 _cell_volume 1372.73(19) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2240 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 26.36 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 7185 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2422 _reflns_number_gt 1999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0449P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2422 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _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 0.8056(2) 0.27345(15) 0.55508(18) 0.0235(5) Uani 1 1 d . . . H1 H 0.8834 0.2838 0.6237 0.028 Uiso 1 1 calc R . . C2 C 0.7354(2) 0.38217(15) 0.52563(19) 0.0261(5) Uani 1 1 d . . . H2 H 0.6612 0.3822 0.4528 0.031 Uiso 1 1 calc R . . C3 C 0.8157(2) 0.48706(15) 0.54703(19) 0.0308(5) Uani 1 1 d . . . H3A H 0.9102 0.4807 0.5844 0.037 Uiso 1 1 calc R . . H3B H 0.7915 0.5460 0.4873 0.037 Uiso 1 1 calc R . . C4 C 0.7215(2) 0.46112(17) 0.6236(2) 0.0377(6) Uani 1 1 d . . . H4A H 0.6404 0.5044 0.6102 0.045 Uiso 1 1 calc R . . H4B H 0.7591 0.4392 0.7073 0.045 Uiso 1 1 calc R . . C5 C 0.8501(2) 0.22642(15) 0.45019(18) 0.0239(5) Uani 1 1 d . . . H2' H 0.7798 0.2166 0.3753 0.029 Uiso 1 1 calc R . . C6 C 0.9824(2) 0.26393(16) 0.43243(19) 0.0265(5) Uani 1 1 d . . . H6A H 0.9887 0.2783 0.3500 0.032 Uiso 1 1 calc R . . H6B H 1.0363 0.3122 0.4937 0.032 Uiso 1 1 calc R . . C7 C 0.9645(2) 0.14583(17) 0.4672(2) 0.0318(5) Uani 1 1 d . . . H7A H 1.0076 0.1229 0.5495 0.038 Uiso 1 1 calc R . . H7B H 0.9601 0.0890 0.4057 0.038 Uiso 1 1 calc R . . C8 C 0.70913(19) -0.01615(15) 0.56499(16) 0.0196(4) Uani 1 1 d . . . C9 C 0.72261(19) -0.12970(15) 0.59507(16) 0.0189(4) Uani 1 1 d . . . C10 C 0.66794(19) -0.21348(15) 0.51544(18) 0.0208(4) Uani 1 1 d . . . H10 H 0.6783 -0.2877 0.5387 0.025 Uiso 1 1 calc R . . C11 C 0.59746(18) -0.18366(15) 0.40035(17) 0.0196(4) Uani 1 1 d . . . C12 C 0.57966(19) -0.07242(15) 0.36566(17) 0.0209(4) Uani 1 1 d . . . H12 H 0.5309 -0.0539 0.2878 0.025 Uiso 1 1 calc R . . C13 C 0.63419(19) 0.00961(16) 0.44669(16) 0.0208(4) Uani 1 1 d . . . H13 H 0.6215 0.0836 0.4231 0.025 Uiso 1 1 calc R . . N1 N 0.79917(16) -0.16134(14) 0.71537(15) 0.0232(4) Uani 1 1 d . . . N2 N 0.54220(16) -0.27114(14) 0.31297(16) 0.0255(4) Uani 1 1 d . . . O1 O 0.70901(14) 0.19954(10) 0.59352(12) 0.0261(3) Uani 1 1 d . . . O2 O 0.85821(14) -0.08532(11) 0.78107(12) 0.0308(4) Uani 1 1 d . . . O3 O 0.80318(14) -0.25923(11) 0.74721(13) 0.0298(4) Uani 1 1 d . . . O4 O 0.56551(15) -0.36875(11) 0.34369(13) 0.0347(4) Uani 1 1 d . . . O5 O 0.47725(14) -0.24267(11) 0.21161(13) 0.0332(4) Uani 1 1 d . . . S1 S 0.77318(5) 0.08814(4) 0.67059(4) 0.02457(16) 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 0.0230(11) 0.0206(11) 0.0265(11) -0.0005(8) 0.0053(9) -0.0056(9) C2 0.0273(12) 0.0216(11) 0.0293(12) 0.0000(9) 0.0072(9) 0.0003(9) C3 0.0302(13) 0.0220(11) 0.0397(13) 0.0038(10) 0.0079(10) -0.0013(10) C4 0.0542(16) 0.0260(12) 0.0380(13) -0.0011(10) 0.0210(12) 0.0022(11) C5 0.0223(11) 0.0205(11) 0.0281(12) -0.0027(8) 0.0050(9) -0.0032(9) C6 0.0254(12) 0.0253(11) 0.0304(12) 0.0010(9) 0.0096(9) -0.0015(9) C7 0.0336(14) 0.0258(12) 0.0380(14) 0.0014(9) 0.0127(11) 0.0028(10) C8 0.0173(10) 0.0214(10) 0.0216(10) -0.0015(8) 0.0078(8) -0.0013(8) C9 0.0168(11) 0.0231(11) 0.0170(10) 0.0010(8) 0.0047(8) -0.0005(8) C10 0.0171(10) 0.0177(10) 0.0293(12) 0.0003(8) 0.0089(9) 0.0002(8) C11 0.0164(10) 0.0219(11) 0.0207(11) -0.0052(8) 0.0053(8) -0.0021(8) C12 0.0158(10) 0.0279(11) 0.0189(10) 0.0018(9) 0.0039(8) 0.0001(9) C13 0.0219(11) 0.0191(10) 0.0225(11) 0.0014(8) 0.0073(9) -0.0003(8) N1 0.0202(9) 0.0269(10) 0.0242(9) 0.0033(8) 0.0084(8) 0.0011(8) N2 0.0184(9) 0.0294(10) 0.0292(11) -0.0056(8) 0.0066(8) -0.0007(8) O1 0.0276(8) 0.0189(7) 0.0342(8) -0.0008(6) 0.0123(6) -0.0034(6) O2 0.0333(9) 0.0335(9) 0.0219(8) -0.0034(6) -0.0003(6) -0.0083(7) O3 0.0337(9) 0.0261(8) 0.0291(8) 0.0096(6) 0.0072(7) 0.0037(7) O4 0.0373(10) 0.0195(8) 0.0431(10) -0.0061(7) 0.0020(7) 0.0006(7) O5 0.0310(9) 0.0382(9) 0.0257(9) -0.0078(7) -0.0019(7) 0.0012(7) S1 0.0291(3) 0.0217(3) 0.0228(3) -0.0027(2) 0.0062(2) -0.0062(2) _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 O1 1.485(2) . ? C1 C5 1.491(3) . ? C1 C2 1.494(3) . ? C1 H1 0.9800 . ? C2 C4 1.496(3) . ? C2 C3 1.498(3) . ? C2 H2 0.9800 . ? C3 C4 1.493(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.506(3) . ? C5 C7 1.508(3) . ? C5 H2 0.9800 . ? C6 C7 1.499(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.407(3) . ? C8 C13 1.409(3) . ? C8 S1 1.7484(19) . ? C9 C10 1.378(3) . ? C9 N1 1.450(2) . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 C12 1.394(3) . ? C11 N2 1.462(2) . ? C12 C13 1.372(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? N1 O3 1.2296(19) . ? N1 O2 1.241(2) . ? N2 O5 1.229(2) . ? N2 O4 1.232(2) . ? O1 S1 1.6479(14) . ? 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 O1 C1 C5 111.90(15) . . ? O1 C1 C2 105.24(15) . . ? C5 C1 C2 112.58(16) . . ? O1 C1 H1 109.0 . . ? C5 C1 H1 109.0 . . ? C2 C1 H1 109.0 . . ? C1 C2 C4 121.42(19) . . ? C1 C2 C3 118.73(18) . . ? C4 C2 C3 59.82(13) . . ? C1 C2 H2 115.2 . . ? C4 C2 H2 115.2 . . ? C3 C2 H2 115.2 . . ? C4 C3 C2 60.02(13) . . ? C4 C3 H3A 117.8 . . ? C2 C3 H3A 117.8 . . ? C4 C3 H3B 117.8 . . ? C2 C3 H3B 117.8 . . ? H3A C3 H3B 114.9 . . ? C3 C4 C2 60.16(13) . . ? C3 C4 H4A 117.8 . . ? C2 C4 H4A 117.8 . . ? C3 C4 H4B 117.8 . . ? C2 C4 H4B 117.8 . . ? H4A C4 H4B 114.9 . . ? C1 C5 C6 117.81(17) . . ? C1 C5 C7 122.12(18) . . ? C6 C5 C7 59.63(13) . . ? C1 C5 H2 115.3 . . ? C6 C5 H2 115.3 . . ? C7 C5 H2 115.3 . . ? C7 C6 C5 60.27(12) . . ? C7 C6 H6A 117.7 . . ? C5 C6 H6A 117.7 . . ? C7 C6 H6B 117.7 . . ? C5 C6 H6B 117.7 . . ? H6A C6 H6B 114.9 . . ? C6 C7 C5 60.10(13) . . ? C6 C7 H7A 117.8 . . ? C5 C7 H7A 117.8 . . ? C6 C7 H7B 117.8 . . ? C5 C7 H7B 117.8 . . ? H7A C7 H7B 114.9 . . ? C9 C8 C13 116.30(17) . . ? C9 C8 S1 122.19(14) . . ? C13 C8 S1 121.41(14) . . ? C10 C9 C8 123.45(18) . . ? C10 C9 N1 117.74(17) . . ? C8 C9 N1 118.81(16) . . ? C11 C10 C9 117.82(17) . . ? C11 C10 H10 121.1 . . ? C9 C10 H10 121.1 . . ? C10 C11 C12 121.33(17) . . ? C10 C11 N2 118.84(17) . . ? C12 C11 N2 119.83(17) . . ? C13 C12 C11 119.85(18) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C8 121.24(18) . . ? C12 C13 H13 119.4 . . ? C8 C13 H13 119.4 . . ? O3 N1 O2 123.61(17) . . ? O3 N1 C9 119.94(16) . . ? O2 N1 C9 116.45(15) . . ? O5 N2 O4 123.66(16) . . ? O5 N2 C11 117.77(16) . . ? O4 N2 C11 118.56(17) . . ? C1 O1 S1 115.46(12) . . ? O1 S1 C8 100.67(8) . . ? 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 O1 C1 C2 C4 77.9(2) . . . . ? C5 C1 C2 C4 -159.93(19) . . . . ? O1 C1 C2 C3 148.25(17) . . . . ? C5 C1 C2 C3 -89.6(2) . . . . ? C1 C2 C3 C4 -111.7(2) . . . . ? C1 C2 C4 C3 107.2(2) . . . . ? O1 C1 C5 C6 -156.02(16) . . . . ? C2 C1 C5 C6 85.7(2) . . . . ? O1 C1 C5 C7 -86.1(2) . . . . ? C2 C1 C5 C7 155.58(18) . . . . ? C1 C5 C6 C7 112.8(2) . . . . ? C1 C5 C7 C6 -105.7(2) . . . . ? C13 C8 C9 C10 0.5(3) . . . . ? S1 C8 C9 C10 176.92(15) . . . . ? C13 C8 C9 N1 179.71(15) . . . . ? S1 C8 C9 N1 -3.9(2) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? N1 C9 C10 C11 -178.71(16) . . . . ? C9 C10 C11 C12 -1.1(3) . . . . ? C9 C10 C11 N2 178.03(16) . . . . ? C10 C11 C12 C13 0.7(3) . . . . ? N2 C11 C12 C13 -178.45(17) . . . . ? C11 C12 C13 C8 0.4(3) . . . . ? C9 C8 C13 C12 -0.9(3) . . . . ? S1 C8 C13 C12 -177.39(15) . . . . ? C10 C9 N1 O3 -6.8(2) . . . . ? C8 C9 N1 O3 173.98(16) . . . . ? C10 C9 N1 O2 173.09(17) . . . . ? C8 C9 N1 O2 -6.2(2) . . . . ? C10 C11 N2 O5 178.48(17) . . . . ? C12 C11 N2 O5 -2.4(2) . . . . ? C10 C11 N2 O4 -3.1(3) . . . . ? C12 C11 N2 O4 176.06(17) . . . . ? C5 C1 O1 S1 75.52(18) . . . . ? C2 C1 O1 S1 -161.91(12) . . . . ? C1 O1 S1 C8 -111.02(13) . . . . ? C9 C8 S1 O1 -171.62(15) . . . . ? C13 C8 S1 O1 4.62(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.311 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.048 data_jmwnf26 _database_code_depnum_ccdc_archive 'CCDC 265216' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 N3 O7' _chemical_formula_weight 283.20 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 6.1596(6) _cell_length_b 7.9020(8) _cell_length_c 24.235(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1179.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2815 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 26.26 _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 7329 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2651 _reflns_number_gt 2383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0411P)^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 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 0.4(11) _refine_ls_number_reflns 2651 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 1.1217(3) 0.8553(2) 0.17385(7) 0.0286(4) Uani 1 1 d . . . H1A H 1.0506 0.9052 0.2056 0.034 Uiso 1 1 calc R . . H1B H 1.0467 0.7514 0.1643 0.034 Uiso 1 1 calc R . . C2 C 1.3520(3) 0.8197(2) 0.18655(8) 0.0340(4) Uani 1 1 d . . . H2 H 1.4387 0.9159 0.1994 0.041 Uiso 1 1 calc R . . C3 C 1.4050(4) 0.6523(3) 0.21140(8) 0.0418(5) Uani 1 1 d . . . H3A H 1.5193 0.6481 0.2389 0.050 Uiso 1 1 calc R . . H3B H 1.2869 0.5731 0.2172 0.050 Uiso 1 1 calc R . . C4 C 1.4674(3) 0.6921(3) 0.15356(9) 0.0437(5) Uani 1 1 d . . . H4A H 1.6199 0.7115 0.1459 0.052 Uiso 1 1 calc R . . H4B H 1.3877 0.6365 0.1242 0.052 Uiso 1 1 calc R . . C5 C 0.9195(3) 1.0372(2) 0.11399(6) 0.0211(3) Uani 1 1 d . . . C6 C 0.8277(3) 1.1824(2) 0.13834(6) 0.0228(4) Uani 1 1 d . . . C7 C 0.6295(2) 1.2469(2) 0.12131(6) 0.0228(4) Uani 1 1 d . . . H7 H 0.5696 1.3414 0.1384 0.027 Uiso 1 1 calc R . . C8 C 0.5237(3) 1.1677(2) 0.07848(6) 0.0230(4) Uani 1 1 d . . . C9 C 0.6106(3) 1.0316(2) 0.05035(6) 0.0235(4) Uani 1 1 d . . . H9 H 0.5409 0.9842 0.0200 0.028 Uiso 1 1 calc R . . C10 C 0.8051(3) 0.9696(2) 0.06937(6) 0.0222(4) Uani 1 1 d . . . N1 N 0.9015(2) 0.82553(19) 0.03931(6) 0.0278(3) Uani 1 1 d . . . N2 N 0.3111(2) 1.23291(19) 0.06038(6) 0.0269(3) Uani 1 1 d . . . N3 N 0.9457(2) 1.28188(19) 0.18049(5) 0.0272(3) Uani 1 1 d . . . O1 O 1.11701(17) 0.97438(15) 0.12676(4) 0.0238(3) Uani 1 1 d . . . O2 O 0.9402(2) 0.69691(17) 0.06486(5) 0.0402(4) Uani 1 1 d . . . O3 O 0.9322(2) 0.84530(19) -0.01019(5) 0.0415(3) Uani 1 1 d . . . O4 O 0.2241(2) 1.16151(17) 0.02117(5) 0.0354(3) Uani 1 1 d . . . O5 O 0.2326(2) 1.35193(17) 0.08565(5) 0.0367(3) Uani 1 1 d . . . O6 O 0.8913(2) 1.42856(16) 0.18663(5) 0.0384(3) Uani 1 1 d . . . O7 O 1.0908(2) 1.21371(18) 0.20654(5) 0.0423(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 0.0309(9) 0.0309(9) 0.0238(8) 0.0071(8) 0.0009(7) 0.0051(9) C2 0.0319(10) 0.0317(10) 0.0383(10) 0.0044(9) -0.0117(8) -0.0013(8) C3 0.0355(11) 0.0434(12) 0.0466(11) 0.0109(10) -0.0065(10) 0.0049(11) C4 0.0339(11) 0.0443(13) 0.0529(12) 0.0104(10) 0.0048(9) 0.0077(10) C5 0.0189(8) 0.0246(8) 0.0199(7) 0.0046(7) 0.0022(6) 0.0002(7) C6 0.0240(8) 0.0258(9) 0.0186(7) 0.0020(7) 0.0000(6) -0.0011(7) C7 0.0226(8) 0.0239(9) 0.0218(7) 0.0028(7) 0.0053(7) 0.0026(7) C8 0.0184(8) 0.0253(9) 0.0251(8) 0.0092(7) 0.0003(6) -0.0015(7) C9 0.0237(8) 0.0263(9) 0.0203(7) 0.0017(7) -0.0016(7) -0.0050(8) C10 0.0223(8) 0.0239(9) 0.0202(8) 0.0008(7) 0.0042(6) -0.0004(7) N1 0.0234(7) 0.0324(9) 0.0275(7) -0.0047(7) -0.0027(6) 0.0029(7) N2 0.0186(7) 0.0298(8) 0.0325(8) 0.0104(7) 0.0004(6) 0.0008(7) N3 0.0260(8) 0.0333(8) 0.0223(7) -0.0032(7) -0.0007(6) 0.0025(7) O1 0.0199(6) 0.0301(7) 0.0215(5) 0.0042(5) -0.0013(5) 0.0041(5) O2 0.0505(9) 0.0306(7) 0.0394(7) -0.0017(6) -0.0015(6) 0.0123(7) O3 0.0507(8) 0.0492(8) 0.0246(6) -0.0085(6) 0.0054(6) 0.0094(7) O4 0.0262(7) 0.0491(9) 0.0309(7) 0.0100(6) -0.0078(5) -0.0016(6) O5 0.0243(7) 0.0313(7) 0.0543(8) 0.0048(7) 0.0014(6) 0.0064(6) O6 0.0435(8) 0.0316(7) 0.0403(7) -0.0117(6) -0.0067(7) 0.0039(7) O7 0.0427(8) 0.0485(9) 0.0356(7) -0.0106(6) -0.0185(7) 0.0104(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 C2 1.478(3) . ? C1 O1 1.4792(19) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C4 1.470(3) . ? C2 C3 1.490(3) . ? C2 H2 0.9800 . ? C3 C4 1.487(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O1 1.350(2) . ? C5 C10 1.397(2) . ? C5 C6 1.409(2) . ? C6 C7 1.385(2) . ? C6 N3 1.480(2) . ? C7 C8 1.376(2) . ? C7 H7 0.9300 . ? C8 C9 1.381(2) . ? C8 N2 1.474(2) . ? C9 C10 1.374(2) . ? C9 H9 0.9300 . ? C10 N1 1.476(2) . ? N1 O2 1.2137(19) . ? N1 O3 1.2245(18) . ? N2 O5 1.2219(19) . ? N2 O4 1.2280(18) . ? N3 O6 1.2156(19) . ? N3 O7 1.2196(18) . ? 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 O1 107.49(14) . . ? C2 C1 H1A 110.2 . . ? O1 C1 H1A 110.2 . . ? C2 C1 H1B 110.2 . . ? O1 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? C4 C2 C1 118.77(17) . . ? C4 C2 C3 60.32(14) . . ? C1 C2 C3 117.63(17) . . ? C4 C2 H2 116.2 . . ? C1 C2 H2 116.2 . . ? C3 C2 H2 116.2 . . ? C4 C3 C2 59.17(13) . . ? C4 C3 H3A 117.9 . . ? C2 C3 H3A 117.9 . . ? C4 C3 H3B 117.9 . . ? C2 C3 H3B 117.9 . . ? H3A C3 H3B 115.0 . . ? C2 C4 C3 60.50(13) . . ? C2 C4 H4A 117.7 . . ? C3 C4 H4A 117.7 . . ? C2 C4 H4B 117.7 . . ? C3 C4 H4B 117.7 . . ? H4A C4 H4B 114.8 . . ? O1 C5 C10 119.42(15) . . ? O1 C5 C6 124.45(15) . . ? C10 C5 C6 115.67(15) . . ? C7 C6 C5 121.92(15) . . ? C7 C6 N3 116.29(15) . . ? C5 C6 N3 121.63(15) . . ? C8 C7 C6 118.33(16) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C7 C8 C9 122.86(16) . . ? C7 C8 N2 119.09(15) . . ? C9 C8 N2 118.02(15) . . ? C10 C9 C8 116.76(15) . . ? C10 C9 H9 121.6 . . ? C8 C9 H9 121.6 . . ? C9 C10 C5 124.26(15) . . ? C9 C10 N1 117.41(14) . . ? C5 C10 N1 118.29(14) . . ? O2 N1 O3 125.20(15) . . ? O2 N1 C10 118.21(13) . . ? O3 N1 C10 116.57(14) . . ? O5 N2 O4 124.70(15) . . ? O5 N2 C8 118.11(15) . . ? O4 N2 C8 117.19(14) . . ? O6 N3 O7 124.03(15) . . ? O6 N3 C6 117.10(14) . . ? O7 N3 C6 118.87(14) . . ? C5 O1 C1 115.37(12) . . ? 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 O1 C1 C2 C4 -81.8(2) . . . . ? O1 C1 C2 C3 -151.35(16) . . . . ? C1 C2 C3 C4 109.1(2) . . . . ? C1 C2 C4 C3 -107.22(19) . . . . ? O1 C5 C6 C7 176.15(14) . . . . ? C10 C5 C6 C7 4.0(2) . . . . ? O1 C5 C6 N3 1.0(2) . . . . ? C10 C5 C6 N3 -171.13(14) . . . . ? C5 C6 C7 C8 -1.5(2) . . . . ? N3 C6 C7 C8 173.91(14) . . . . ? C6 C7 C8 C9 -2.8(2) . . . . ? C6 C7 C8 N2 179.05(14) . . . . ? C7 C8 C9 C10 4.2(2) . . . . ? N2 C8 C9 C10 -177.69(14) . . . . ? C8 C9 C10 C5 -1.3(2) . . . . ? C8 C9 C10 N1 -179.23(15) . . . . ? O1 C5 C10 C9 -175.16(14) . . . . ? C6 C5 C10 C9 -2.6(2) . . . . ? O1 C5 C10 N1 2.7(2) . . . . ? C6 C5 C10 N1 175.29(14) . . . . ? C9 C10 N1 O2 -122.77(17) . . . . ? C5 C10 N1 O2 59.2(2) . . . . ? C9 C10 N1 O3 55.9(2) . . . . ? C5 C10 N1 O3 -122.18(17) . . . . ? C7 C8 N2 O5 -2.7(2) . . . . ? C9 C8 N2 O5 179.10(15) . . . . ? C7 C8 N2 O4 178.24(14) . . . . ? C9 C8 N2 O4 0.0(2) . . . . ? C7 C6 N3 O6 -18.1(2) . . . . ? C5 C6 N3 O6 157.35(15) . . . . ? C7 C6 N3 O7 162.38(14) . . . . ? C5 C6 N3 O7 -22.2(2) . . . . ? C10 C5 O1 C1 -101.21(17) . . . . ? C6 C5 O1 C1 86.94(19) . . . . ? C2 C1 O1 C5 -172.08(15) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.218 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.045