data_test1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5LIO-Me-3,2-HOPO _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H26 N4 O9' _chemical_formula_weight 442.43 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 24.438(11) _cell_length_b 9.722(6) _cell_length_c 8.925(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2120.5(18) _cell_formula_units_Z 4 _cell_measurement_temperature 135(2) _cell_measurement_reflns_used 3700 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 25.7 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 135(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 SMART 1000' _diffrn_measurement_method '\w/2\q-scans' _diffrn_detector_area_resol_mean '81.92' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 4472 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1892 _reflns_number_gt 1285 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v.5.059' _computing_cell_refinement 'SAINT v.4.024' _computing_data_reduction 'SAINT v.4.024' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'teXsan, Mol. Structure Corp. 1985, 1992)' _computing_molecular_graphics 'ORTEP-3 v.1.08, POV-Ray v3.6.1c.icl8.win32' _computing_publication_material 'ORTEP-3 v.1.08, POV-Ray v3.6.1c.icl8.win32' _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^)+(0.0598P)^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(10) _refine_ls_number_reflns 1892 _refine_ls_number_parameters 292 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0886 _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 O1 O 0.28719(12) 0.5706(3) 0.5060(3) 0.0629(8) Uani 1 1 d . . . O1W O 0.04196(16) 1.0243(4) 0.0033(5) 0.0819(10) Uani 1 1 d . . . H1W2 H 0.068(3) 0.981(6) 0.058(8) 0.123 Uiso 1 1 d . . . H1W1 H 0.042(2) 0.990(6) -0.095(8) 0.123 Uiso 1 1 d . . . O2 O 0.17679(12) 0.6014(3) 0.4879(3) 0.0635(8) Uani 1 1 d . . . H2A H 0.1958 0.5526 0.5456 0.095 Uiso 1 1 calc R . . O2W O 0.05256(16) -0.0261(4) 0.6867(4) 0.0842(11) Uani 1 1 d D . . H2W1 H 0.078(3) 0.028(6) 0.640(8) 0.126 Uiso 1 1 d . . . H2W2 H 0.0236(18) -0.030(6) 0.635(7) 0.126 Uiso 1 1 d D . . O3 O 0.11683(14) 0.8869(3) 0.1805(4) 0.0829(10) Uani 1 1 d . . . O4 O 0.03512(12) 0.4670(3) 0.3323(4) 0.0762(9) Uani 1 1 d . . . O5 O 0.13811(12) 0.0885(3) 0.5164(3) 0.0762(9) Uani 1 1 d . . . O6 O 0.19370(11) 0.3880(3) 0.2164(3) 0.0574(8) Uani 1 1 d . . . H6A H 0.2120 0.4370 0.1574 0.086 Uiso 1 1 calc R . . O7 O 0.30361(11) 0.4203(3) 0.1915(3) 0.0619(8) Uani 1 1 d . . . N1 N 0.30189(15) 0.7398(3) 0.3354(4) 0.0517(9) Uani 1 1 d . . . N2 N 0.09456(17) 0.7110(3) 0.3320(5) 0.0772(12) Uani 1 1 d . . . H2B H 0.1071 0.6515 0.3979 0.093 Uiso 1 1 calc R . . N3 N 0.11262(14) 0.2548(3) 0.3559(5) 0.0613(10) Uani 1 1 d . . . H3A H 0.1235 0.3203 0.2947 0.074 Uiso 1 1 calc R . . N4 N 0.32027(14) 0.2566(3) 0.3646(4) 0.0498(9) Uani 1 1 d . . . C1 C 0.36063(18) 0.7155(4) 0.3455(5) 0.0680(13) Uani 1 1 d . . . H1A H 0.3690 0.6230 0.3083 0.082 Uiso 1 1 calc R . . H1B H 0.3723 0.7234 0.4501 0.082 Uiso 1 1 calc R . . H1C H 0.3801 0.7838 0.2847 0.082 Uiso 1 1 calc R . . C2 C 0.26777(19) 0.6587(3) 0.4195(5) 0.0492(10) Uani 1 1 d . . . C3 C 0.21004(16) 0.6805(3) 0.4028(4) 0.0455(10) Uani 1 1 d . . . C4 C 0.18985(19) 0.7751(3) 0.3042(5) 0.0517(11) Uani 1 1 d . . . C5 C 0.2274(2) 0.8548(4) 0.2238(5) 0.0606(13) Uani 1 1 d . . . H5A H 0.2143 0.9231 0.1567 0.073 Uiso 1 1 calc R . . C6 C 0.2815(2) 0.8368(4) 0.2394(5) 0.0610(13) Uani 1 1 d . . . H6B H 0.3060 0.8923 0.1831 0.073 Uiso 1 1 calc R . . C7 C 0.1303(2) 0.7954(4) 0.2699(5) 0.0599(12) Uani 1 1 d . . . C8 C 0.0360(2) 0.7080(5) 0.3005(6) 0.0851(16) Uani 1 1 d . . . H8A H 0.0265 0.7842 0.2317 0.102 Uiso 1 1 calc R . . H8B H 0.0153 0.7210 0.3948 0.102 Uiso 1 1 calc R . . C9 C 0.0203(2) 0.5728(5) 0.2304(6) 0.0845(15) Uani 1 1 d . . . H9A H -0.0196 0.5703 0.2111 0.101 Uiso 1 1 calc R . . H9B H 0.0397 0.5604 0.1340 0.101 Uiso 1 1 calc R . . C10 C 0.02340(19) 0.3325(4) 0.2803(6) 0.0802(14) Uani 1 1 d . . . H10A H 0.0343 0.3232 0.1740 0.096 Uiso 1 1 calc R . . H10B H -0.0163 0.3139 0.2883 0.096 Uiso 1 1 calc R . . C11 C 0.05475(18) 0.2326(4) 0.3748(7) 0.0739(14) Uani 1 1 d . . . H11A H 0.0447 0.2448 0.4815 0.089 Uiso 1 1 calc R . . H11B H 0.0453 0.1373 0.3452 0.089 Uiso 1 1 calc R . . C12 C 0.15038(18) 0.1804(4) 0.4271(5) 0.0525(10) Uani 1 1 d . . . C13 C 0.20848(17) 0.2120(3) 0.3973(5) 0.0471(10) Uani 1 1 d . . . C14 C 0.22805(17) 0.3086(3) 0.2990(5) 0.0448(10) Uani 1 1 d . . . C15 C 0.28550(16) 0.3332(3) 0.2798(4) 0.0446(10) Uani 1 1 d . . . C16 C 0.37846(17) 0.2860(4) 0.3528(6) 0.0685(13) Uani 1 1 d . . . H16A H 0.3857 0.3791 0.3900 0.082 Uiso 1 1 calc R . . H16B H 0.3898 0.2794 0.2477 0.082 Uiso 1 1 calc R . . H16C H 0.3991 0.2193 0.4127 0.082 Uiso 1 1 calc R . . C17 C 0.30127(19) 0.1590(4) 0.4629(5) 0.0575(12) Uani 1 1 d . . . H17A H 0.3266 0.1074 0.5209 0.069 Uiso 1 1 calc R . . C18 C 0.2479(2) 0.1355(4) 0.4783(6) 0.0568(11) Uani 1 1 d . . . H18A H 0.2359 0.0658 0.5453 0.068 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 O1 0.0642(19) 0.0687(17) 0.0557(19) 0.0237(16) -0.0036(16) 0.0011(14) O1W 0.065(3) 0.099(2) 0.082(2) 0.018(2) -0.005(2) 0.0087(18) O2 0.062(2) 0.0713(17) 0.0574(18) 0.0268(16) -0.0009(16) 0.0015(14) O2W 0.065(3) 0.117(3) 0.071(2) 0.027(2) 0.0029(19) -0.010(2) O3 0.091(2) 0.0795(19) 0.078(2) 0.0319(19) -0.014(2) 0.0158(18) O4 0.074(2) 0.078(2) 0.076(2) 0.0132(18) -0.0085(19) 0.0047(15) O5 0.068(2) 0.0779(18) 0.083(2) 0.0304(17) 0.0104(19) -0.0111(16) O6 0.0506(19) 0.0622(16) 0.0592(18) 0.0232(15) 0.0044(16) 0.0007(13) O7 0.061(2) 0.0625(17) 0.0626(19) 0.0253(16) 0.0017(16) -0.0066(14) N1 0.058(3) 0.0488(17) 0.048(2) 0.0053(16) -0.0054(18) -0.0071(15) N2 0.067(3) 0.074(2) 0.090(3) 0.032(2) -0.012(2) 0.0068(19) N3 0.047(3) 0.0630(18) 0.074(2) 0.0179(18) 0.007(2) -0.0039(16) N4 0.051(3) 0.0481(17) 0.050(2) 0.0081(16) -0.0008(18) 0.0017(15) C1 0.062(4) 0.075(3) 0.067(3) 0.017(3) -0.005(3) -0.015(2) C2 0.065(3) 0.045(2) 0.037(2) 0.0074(19) -0.001(2) -0.0034(19) C3 0.055(3) 0.0458(19) 0.036(2) 0.0055(19) 0.000(2) -0.0015(19) C4 0.071(3) 0.0432(19) 0.041(2) 0.0054(19) -0.004(2) 0.0037(19) C5 0.074(4) 0.049(2) 0.059(3) 0.018(2) -0.006(3) -0.004(2) C6 0.083(5) 0.048(2) 0.053(3) 0.016(2) 0.001(3) -0.012(2) C7 0.074(4) 0.051(2) 0.055(3) 0.002(2) -0.006(3) 0.011(2) C8 0.065(4) 0.084(3) 0.106(4) 0.036(3) 0.001(3) 0.023(2) C9 0.064(3) 0.093(3) 0.097(4) 0.026(3) -0.012(3) 0.008(3) C10 0.054(3) 0.084(3) 0.103(4) 0.001(3) -0.006(3) -0.007(2) C11 0.052(4) 0.077(3) 0.092(4) 0.014(3) 0.006(3) -0.004(2) C12 0.061(3) 0.048(2) 0.048(3) 0.005(2) 0.003(2) -0.003(2) C13 0.047(3) 0.0424(19) 0.052(3) 0.0023(19) 0.004(2) -0.0063(17) C14 0.049(3) 0.0397(18) 0.046(2) 0.0057(18) 0.000(2) 0.0027(17) C15 0.050(3) 0.043(2) 0.041(2) 0.0065(19) -0.002(2) -0.0013(18) C16 0.048(4) 0.072(3) 0.085(4) 0.013(3) -0.007(3) 0.000(2) C17 0.060(4) 0.049(2) 0.064(3) 0.016(2) -0.011(2) 0.0018(19) C18 0.056(3) 0.053(2) 0.062(3) 0.025(2) -0.001(2) -0.001(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 O1 C2 1.248(4) . ? O2 C3 1.352(4) . ? O3 C7 1.240(5) . ? O4 C10 1.416(5) . ? O4 C9 1.420(5) . ? O5 C12 1.235(4) . ? O6 C14 1.358(5) . ? O7 C15 1.239(4) . ? N1 C6 1.369(5) . ? N1 C2 1.371(5) . ? N1 C1 1.457(5) . ? N2 C7 1.320(6) . ? N2 C8 1.459(5) . ? N3 C12 1.333(5) . ? N3 C11 1.440(5) . ? N4 C15 1.360(5) . ? N4 C17 1.373(5) . ? N4 C16 1.454(5) . ? C2 C3 1.434(5) . ? C3 C4 1.366(5) . ? C4 C5 1.398(6) . ? C4 C7 1.500(6) . ? C5 C6 1.340(6) . ? C8 C9 1.505(7) . ? C10 C11 1.497(6) . ? C12 C13 1.477(6) . ? C13 C14 1.371(5) . ? C13 C18 1.414(6) . ? C14 C15 1.434(5) . ? C17 C18 1.332(6) . ? 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 C10 O4 C9 114.1(4) . . ? C6 N1 C2 121.1(4) . . ? C6 N1 C1 120.6(4) . . ? C2 N1 C1 118.2(3) . . ? C7 N2 C8 125.5(4) . . ? C12 N3 C11 122.8(3) . . ? C15 N4 C17 121.5(4) . . ? C15 N4 C16 117.6(3) . . ? C17 N4 C16 120.9(4) . . ? O1 C2 N1 120.2(4) . . ? O1 C2 C3 122.6(4) . . ? N1 C2 C3 117.2(3) . . ? O2 C3 C4 121.9(4) . . ? O2 C3 C2 116.7(3) . . ? C4 C3 C2 121.4(3) . . ? C3 C4 C5 117.8(4) . . ? C3 C4 C7 124.8(4) . . ? C5 C4 C7 117.3(4) . . ? C6 C5 C4 121.4(4) . . ? C5 C6 N1 121.0(4) . . ? O3 C7 N2 122.7(4) . . ? O3 C7 C4 118.9(4) . . ? N2 C7 C4 118.3(4) . . ? N2 C8 C9 110.4(4) . . ? O4 C9 C8 107.5(4) . . ? O4 C10 C11 108.1(4) . . ? N3 C11 C10 109.8(4) . . ? O5 C12 N3 122.2(4) . . ? O5 C12 C13 120.0(4) . . ? N3 C12 C13 117.8(3) . . ? C14 C13 C18 116.7(4) . . ? C14 C13 C12 126.4(4) . . ? C18 C13 C12 116.9(4) . . ? O6 C14 C13 121.4(4) . . ? O6 C14 C15 116.4(3) . . ? C13 C14 C15 122.1(4) . . ? O7 C15 N4 120.4(4) . . ? O7 C15 C14 122.7(4) . . ? N4 C15 C14 117.0(3) . . ? C18 C17 N4 121.0(4) . . ? C17 C18 C13 121.6(4) . . ? _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.850 _refine_diff_density_max 0.126 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.032