data_jac01 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N O6' _chemical_formula_sum 'C13 H15 N O6' _chemical_formula_weight 281.26 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' '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 6.9163(3) _cell_length_b 20.5882(8) _cell_length_c 9.3847(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.402(2) _cell_angle_gamma 90.00 _cell_volume 1330.39(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9198 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 31.03 _exptl_crystal_description Colorless _exptl_crystal_colour Fragment _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9768 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker KAPPA APEX II' _diffrn_measurement_method '\w scans; 10 settings' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 30667 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 31.11 _reflns_number_total 4258 _reflns_number_gt 3426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.7-0' _computing_cell_refinement 'Bruker SAINT-Plus v7.66A' _computing_data_reduction 'Bruker SAINT-Plus v7.66A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker XP v5.1' _computing_publication_material 'Bruker XCIF 2008' _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 matrix' _refine_ls_weighting_scheme Sigma _refine_ls_weighting_details 'w=1/s^2^(Fo^2^)' _atom_sites_solution_primary 'Direct methods' _atom_sites_solution_secondary 'Difference Fourier map' _atom_sites_solution_hydrogens 'Difference Fourier map' _refine_ls_hydrogen_treatment Unrestrained _chemical_absolute_configuration ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4258 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.0618 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 2.394 _refine_ls_restrained_S_all 2.394 _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 O1 O 0.32644(10) 0.38906(4) 0.84220(8) 0.02539(18) Uani 1 1 d . . . O2 O 0.17572(11) 0.47803(4) 0.75353(9) 0.0343(2) Uani 1 1 d . . . O3 O 0.23408(10) 0.42069(4) 0.33724(8) 0.02341(18) Uani 1 1 d . . . O4 O 0.43879(10) 0.38485(4) 0.52105(8) 0.0296(2) Uani 1 1 d . . . O5 O 0.26481(9) 0.19264(3) 0.65917(7) 0.01834(16) Uani 1 1 d . . . O6 O 0.24640(9) 0.21733(4) 0.42174(7) 0.01970(17) Uani 1 1 d . . . N1 N 0.17200(11) 0.29177(4) 0.58761(9) 0.01597(18) Uani 1 1 d . . . C1 C 0.17566(15) 0.42011(6) 0.76917(12) 0.0237(3) Uani 1 1 d . . . C2 C 0.01993(15) 0.37221(5) 0.71404(12) 0.0195(2) Uani 1 1 d . . . C3 C 0.11934(14) 0.30641(5) 0.73170(11) 0.0159(2) Uani 1 1 d . . . C4 C 0.29522(15) 0.31932(5) 0.84065(11) 0.0196(2) Uani 1 1 d . . . C5 C 0.26283(14) 0.29729(5) 0.98549(12) 0.0214(2) Uani 1 1 d . . . C6 C 0.23233(16) 0.27846(6) 1.10003(13) 0.0269(3) Uani 1 1 d . . . C7 C -0.04200(15) 0.38059(6) 0.55421(12) 0.0216(2) Uani 1 1 d . . . C8 C 0.11246(14) 0.34163(5) 0.48247(11) 0.0175(2) Uani 1 1 d . . . C9 C 0.28403(14) 0.38377(5) 0.45107(11) 0.0183(2) Uani 1 1 d . . . C10 C 0.37522(17) 0.46877(6) 0.29844(13) 0.0259(3) Uani 1 1 d . . . C11 C 0.31213(18) 0.48981(7) 0.14832(13) 0.0282(3) Uani 1 1 d . . . C12 C 0.22960(13) 0.23263(5) 0.54538(11) 0.0159(2) Uani 1 1 d . . . C13 C 0.30163(18) 0.12568(6) 0.62416(14) 0.0242(3) Uani 1 1 d . . . H2 H -0.0877(16) 0.3765(5) 0.7724(12) 0.028(3) Uiso 1 1 d . . . H3 H 0.0409(12) 0.2722(5) 0.7667(10) 0.011(3) Uiso 1 1 d . . . H4 H 0.4127(14) 0.3003(5) 0.8087(10) 0.017(3) Uiso 1 1 d . . . H6 H 0.2132(16) 0.2633(6) 1.1963(13) 0.048(4) Uiso 1 1 d . . . H7A H -0.0460(15) 0.4264(6) 0.5225(11) 0.025(3) Uiso 1 1 d . . . H7B H -0.1755(15) 0.3605(5) 0.5260(11) 0.025(3) Uiso 1 1 d . . . H8 H 0.0612(13) 0.3212(5) 0.3944(11) 0.014(3) Uiso 1 1 d . . . H10A H 0.5033(17) 0.4477(5) 0.3075(12) 0.034(3) Uiso 1 1 d . . . H10B H 0.3760(16) 0.5060(6) 0.3703(13) 0.037(4) Uiso 1 1 d . . . H11A H 0.3197(17) 0.4525(7) 0.0796(14) 0.048(4) Uiso 1 1 d . . . H11B H 0.4040(19) 0.5264(7) 0.1218(14) 0.057(4) Uiso 1 1 d . . . H11C H 0.1742(16) 0.5048(5) 0.1402(12) 0.032(3) Uiso 1 1 d . . . H13A H 0.1871(16) 0.1088(6) 0.5623(12) 0.035(3) Uiso 1 1 d . . . H13B H 0.3193(15) 0.1035(6) 0.7144(13) 0.034(3) Uiso 1 1 d . . . H13C H 0.4195(17) 0.1226(6) 0.5752(13) 0.040(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 O1 0.0280(4) 0.0222(5) 0.0254(4) -0.0047(3) -0.0006(3) -0.0056(3) O2 0.0413(5) 0.0169(5) 0.0459(6) -0.0039(4) 0.0098(4) -0.0032(4) O3 0.0222(4) 0.0237(5) 0.0239(4) 0.0101(3) 0.0001(3) -0.0057(3) O4 0.0212(4) 0.0369(5) 0.0298(5) 0.0107(4) -0.0025(3) -0.0050(4) O5 0.0246(4) 0.0132(4) 0.0170(4) 0.0014(3) 0.0007(3) 0.0015(3) O6 0.0201(4) 0.0238(4) 0.0153(4) -0.0028(3) 0.0018(3) 0.0007(3) N1 0.0201(4) 0.0143(5) 0.0136(4) 0.0014(3) 0.0020(3) 0.0008(4) C1 0.0252(6) 0.0223(7) 0.0249(6) -0.0059(5) 0.0092(5) -0.0010(5) C2 0.0181(5) 0.0172(6) 0.0241(6) -0.0005(5) 0.0069(4) 0.0014(4) C3 0.0161(5) 0.0163(6) 0.0158(5) 0.0002(4) 0.0031(4) -0.0005(4) C4 0.0199(5) 0.0194(6) 0.0196(5) -0.0043(5) 0.0020(4) -0.0002(5) C5 0.0184(5) 0.0235(6) 0.0218(6) -0.0047(5) -0.0012(4) 0.0049(5) C6 0.0226(6) 0.0355(8) 0.0223(6) -0.0007(5) 0.0000(5) 0.0089(5) C7 0.0187(5) 0.0188(6) 0.0273(6) 0.0056(5) 0.0024(4) 0.0017(5) C8 0.0185(5) 0.0169(6) 0.0167(5) 0.0025(4) -0.0006(4) -0.0011(4) C9 0.0216(5) 0.0162(6) 0.0174(5) 0.0008(4) 0.0043(4) 0.0012(4) C10 0.0266(6) 0.0260(7) 0.0255(6) 0.0060(5) 0.0043(5) -0.0086(5) C11 0.0312(7) 0.0288(8) 0.0252(6) 0.0077(6) 0.0053(5) -0.0041(6) C12 0.0136(5) 0.0162(6) 0.0178(5) -0.0001(4) 0.0004(4) -0.0021(4) C13 0.0297(6) 0.0131(6) 0.0293(7) -0.0011(5) 0.0001(5) 0.0009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3532(13) . ? O1 C4 1.4520(13) . ? O2 C1 1.2015(13) . ? O3 C9 1.3300(12) . ? O3 C10 1.4601(13) . ? O4 C9 1.2022(11) . ? O5 C12 1.3522(12) . ? O5 C13 1.4453(13) . ? O6 C12 1.2184(11) . ? N1 C12 1.3522(13) . ? N1 C8 1.4560(13) . ? N1 C3 1.4645(12) . ? C1 C2 1.5150(15) . ? C2 C3 1.5211(14) . ? C2 C7 1.5305(15) . ? C2 H2 0.969(11) . ? C3 C4 1.5368(14) . ? C3 H3 0.965(9) . ? C4 C5 1.4700(15) . ? C4 H4 0.974(10) . ? C5 C6 1.1802(15) . ? C6 H6 0.976(12) . ? C7 C8 1.5406(15) . ? C7 H7A 0.988(11) . ? C7 H7B 1.024(10) . ? C8 C9 1.5210(14) . ? C8 H8 0.965(10) . ? C10 C11 1.4991(16) . ? C10 H10A 0.983(11) . ? C10 H10B 1.021(12) . ? C11 H11A 1.007(13) . ? C11 H11B 1.031(13) . ? C11 H11C 0.998(11) . ? C13 H13A 1.000(11) . ? C13 H13B 0.959(12) . ? C13 H13C 0.975(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C4 110.81(8) . . ? C9 O3 C10 117.29(8) . . ? C12 O5 C13 115.07(8) . . ? C12 N1 C8 120.57(9) . . ? C12 N1 C3 124.17(8) . . ? C8 N1 C3 113.68(8) . . ? O2 C1 O1 121.43(10) . . ? O2 C1 C2 127.79(10) . . ? O1 C1 C2 110.78(10) . . ? C1 C2 C3 104.06(8) . . ? C1 C2 C7 112.68(9) . . ? C3 C2 C7 106.81(9) . . ? C1 C2 H2 107.9(6) . . ? C3 C2 H2 112.5(7) . . ? C7 C2 H2 112.6(7) . . ? N1 C3 C2 103.40(8) . . ? N1 C3 C4 113.57(8) . . ? C2 C3 C4 103.88(8) . . ? N1 C3 H3 111.1(6) . . ? C2 C3 H3 115.1(5) . . ? C4 C3 H3 109.6(5) . . ? O1 C4 C5 109.35(9) . . ? O1 C4 C3 106.58(8) . . ? C5 C4 C3 112.45(9) . . ? O1 C4 H4 105.8(6) . . ? C5 C4 H4 111.4(6) . . ? C3 C4 H4 110.9(6) . . ? C6 C5 C4 178.01(12) . . ? C5 C6 H6 177.4(7) . . ? C2 C7 C8 103.17(8) . . ? C2 C7 H7A 113.6(6) . . ? C8 C7 H7A 111.5(6) . . ? C2 C7 H7B 111.7(6) . . ? C8 C7 H7B 108.8(6) . . ? H7A C7 H7B 108.0(8) . . ? N1 C8 C9 110.94(8) . . ? N1 C8 C7 103.56(8) . . ? C9 C8 C7 111.92(9) . . ? N1 C8 H8 109.3(6) . . ? C9 C8 H8 108.3(6) . . ? C7 C8 H8 112.8(6) . . ? O4 C9 O3 125.37(9) . . ? O4 C9 C8 125.13(9) . . ? O3 C9 C8 109.47(8) . . ? O3 C10 C11 106.74(9) . . ? O3 C10 H10A 107.3(7) . . ? C11 C10 H10A 112.9(7) . . ? O3 C10 H10B 107.9(7) . . ? C11 C10 H10B 112.8(7) . . ? H10A C10 H10B 109.0(9) . . ? C10 C11 H11A 110.7(7) . . ? C10 C11 H11B 107.9(8) . . ? H11A C11 H11B 109.4(10) . . ? C10 C11 H11C 110.6(7) . . ? H11A C11 H11C 107.0(9) . . ? H11B C11 H11C 111.3(10) . . ? O6 C12 N1 124.68(10) . . ? O6 C12 O5 124.65(10) . . ? N1 C12 O5 110.67(9) . . ? O5 C13 H13A 108.5(7) . . ? O5 C13 H13B 105.3(7) . . ? H13A C13 H13B 112.0(9) . . ? O5 C13 H13C 110.1(7) . . ? H13A C13 H13C 110.8(9) . . ? H13B C13 H13C 110.0(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 31.11 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.382 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.050