# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 188/164 #Pseudopolymorphs of 3,5-dinitrosalicylic acid. data_Form_A #(1).(dioxane)0.5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N2 O7 . C2 H4 O2' _chemical_formula_sum 'C9 H8 N2 O8' _chemical_formula_weight 272.17 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.006(4) _cell_length_b 9.517(4) _cell_length_c 10.396(5) _cell_angle_alpha 78.99(3) _cell_angle_beta 73.84(5) _cell_angle_gamma 85.86(5) _cell_volume 560.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description ? _exptl_crystal_colour Yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type none _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time '90 minutes' _diffrn_standards_decay_% 18 _diffrn_reflns_number 1924 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1924 _reflns_number_gt 932 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0947P)^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 1924 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1331 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1766 _refine_ls_wR_factor_gt 0.1469 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.7424(6) 0.2250(4) 0.8130(4) 0.1153(13) Uani 1 1 d . . . O1W O 0.4323(4) 0.5415(3) 0.1279(2) 0.0622(7) Uani 1 1 d . . . O2 O -0.6518(6) 0.3916(5) 0.6387(4) 0.1133(13) Uani 1 1 d . . . O3 O 0.063(2) -0.1669(10) 0.7698(9) 0.111(3) Uani 0.50 1 d P . . O3A O -0.1886(19) -0.0976(12) 0.9212(8) 0.152(4) Uani 0.50 1 d P . . O4 O 0.1813(13) -0.1001(8) 0.8191(9) 0.143(3) Uani 0.60 1 d P . . O4A O -0.146(2) -0.1825(13) 0.8590(12) 0.113(4) Uani 0.40 1 d P . . O5 O 0.1144(4) 0.4188(3) 0.3393(2) 0.0724(8) Uani 1 1 d . . . H5 H 0.2192 0.4510 0.2728 0.109 Uiso 1 1 calc . . . O6 O 0.3766(5) 0.2461(3) 0.3611(3) 0.0779(9) Uani 1 1 d . . . O7 O 0.2839(4) 0.0459(2) 0.5655(2) 0.0693(8) Uani 1 1 d . . . H7 H 0.3613 0.0934 0.4950 0.104 Uiso 1 1 calc . . . N1 N -0.6085(6) 0.2846(5) 0.7116(4) 0.0831(11) Uani 1 1 d . . . N2 N -0.0361(10) -0.0838(5) 0.8078(4) 0.0914(13) Uani 1 1 d . . . C1 C 0.0093(3) 0.2288(2) 0.52082(18) 0.0510(8) Uani 1 1 d G . . C2 C 0.0709(3) 0.1060(2) 0.6009(2) 0.0539(9) Uani 1 1 d G . . C3 C -0.0900(4) 0.04188(19) 0.7178(2) 0.0655(10) Uani 1 1 d G . . C4 C -0.3125(4) 0.1004(3) 0.75467(19) 0.0721(11) Uani 1 1 d G . . H4 H -0.4202 0.0575 0.8329 0.087 Uiso 1 1 calc . . . C5 C -0.3741(3) 0.2232(3) 0.6746(2) 0.0648(10) Uani 1 1 d G . . C6 C -0.2132(4) 0.2873(2) 0.5576(2) 0.0596(10) Uani 1 1 d G . . H6 H -0.2545 0.3694 0.5041 0.072 Uiso 1 1 calc . . . C7 C 0.1833(6) 0.2983(4) 0.4010(3) 0.0567(9) Uani 1 1 d . . . C2W C 0.3518(6) 0.6189(4) 0.0161(4) 0.0631(10) Uani 1 1 d . . . H2W1 H 0.4545 0.6976 -0.0314 0.076 Uiso 1 1 calc . . . H2W2 H 0.1981 0.6588 0.0505 0.076 Uiso 1 1 calc . . . C3W C 0.6565(6) 0.4761(4) 0.0802(4) 0.0654(10) Uani 1 1 d . . . H3W1 H 0.7041 0.4208 0.1570 0.078 Uiso 1 1 calc . . . H3W2 H 0.7697 0.5499 0.0351 0.078 Uiso 1 1 calc . . . 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 0.071(2) 0.146(3) 0.113(3) -0.055(2) 0.028(2) -0.026(2) O1W 0.0548(15) 0.0721(16) 0.0535(14) -0.0073(12) -0.0112(11) 0.0149(12) O2 0.075(2) 0.154(4) 0.113(3) -0.042(3) -0.0263(19) 0.040(2) O3 0.141(9) 0.079(5) 0.119(6) -0.012(5) -0.060(6) 0.041(6) O3A 0.186(9) 0.148(9) 0.059(5) 0.038(5) 0.018(5) 0.054(7) O4 0.118(6) 0.108(5) 0.162(7) 0.050(5) -0.027(5) 0.018(5) O4A 0.122(9) 0.110(9) 0.091(8) 0.050(6) -0.028(7) -0.074(7) O5 0.0683(17) 0.0631(16) 0.0694(16) 0.0016(13) -0.0050(13) 0.0146(13) O6 0.0616(17) 0.0740(18) 0.0765(17) 0.0007(14) 0.0021(14) 0.0195(14) O7 0.0687(17) 0.0572(15) 0.0738(17) -0.0062(13) -0.0124(13) 0.0104(13) N1 0.052(2) 0.113(3) 0.089(3) -0.055(3) -0.003(2) -0.005(2) N2 0.131(4) 0.067(3) 0.070(3) 0.005(2) -0.026(3) -0.011(3) C1 0.049(2) 0.050(2) 0.055(2) -0.0156(17) -0.0124(17) 0.0038(16) C2 0.056(2) 0.045(2) 0.059(2) -0.0161(17) -0.0095(18) 0.0036(16) C3 0.076(3) 0.058(2) 0.057(2) -0.008(2) -0.009(2) -0.010(2) C4 0.073(3) 0.082(3) 0.059(2) -0.025(2) 0.002(2) -0.031(2) C5 0.051(2) 0.076(3) 0.068(2) -0.031(2) -0.0039(19) -0.0051(19) C6 0.054(2) 0.064(2) 0.067(2) -0.025(2) -0.0185(19) 0.0031(18) C7 0.056(2) 0.055(2) 0.054(2) -0.0117(18) -0.0080(18) 0.0104(18) C2W 0.055(2) 0.059(2) 0.064(2) -0.0028(19) -0.0066(18) 0.0107(18) C3W 0.054(2) 0.070(2) 0.070(2) -0.008(2) -0.0193(19) 0.0094(19) _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 N1 1.202(5) . ? O1W C2W 1.436(4) . ? O1W C3W 1.439(4) . ? O2 N1 1.206(5) . ? O3 N2 1.028(8) . ? O3 O4 1.251(11) . ? O3 O4A 1.335(15) . ? O3A O4A 1.103(14) . ? O3A N2 1.266(9) . ? O4 N2 1.339(8) . ? O4A N2 1.142(9) . ? O5 C7 1.303(4) . ? O6 C7 1.222(4) . ? O7 C2 1.346(3) . ? N1 C5 1.462(4) . ? N2 C3 1.447(4) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.464(4) . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C2W C3W 1.484(5) 2_665 ? C3W C2W 1.484(5) 2_665 ? 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 C2W O1W C3W 111.0(2) . . ? N2 O3 O4 71.2(8) . . ? N2 O3 O4A 56.0(8) . . ? O4 O3 O4A 106.4(11) . . ? O4A O3A N2 57.1(6) . . ? O3 O4 N2 46.6(5) . . ? O3A O4A N2 68.7(10) . . ? O3A O4A O3 112.5(12) . . ? N2 O4A O3 48.3(5) . . ? O1 N1 O2 125.2(4) . . ? O1 N1 C5 117.3(5) . . ? O2 N1 C5 117.5(4) . . ? O3 N2 O4A 75.7(10) . . ? O3 N2 O3A 124.3(9) . . ? O4A N2 O3A 54.2(8) . . ? O3 N2 O4 62.2(7) . . ? O4A N2 O4 113.0(8) . . ? O3A N2 O4 113.6(7) . . ? O3 N2 C3 121.1(6) . . ? O4A N2 C3 128.6(8) . . ? O3A N2 C3 109.6(6) . . ? O4 N2 C3 117.6(5) . . ? C2 C1 C6 120.0 . . ? C2 C1 C7 119.3(2) . . ? C6 C1 C7 120.6(2) . . ? O7 C2 C3 119.05(19) . . ? O7 C2 C1 120.93(19) . . ? C3 C2 C1 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 N2 123.0(3) . . ? C4 C3 N2 117.0(3) . . ? C5 C4 C3 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 N1 120.4(3) . . ? C6 C5 N1 119.6(3) . . ? C5 C6 C1 120.0 . . ? O6 C7 O5 122.8(3) . . ? O6 C7 C1 122.6(3) . . ? O5 C7 C1 114.6(3) . . ? O1W C2W C3W 110.9(3) . 2_665 ? O1W C3W C2W 110.4(3) . 2_665 ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.193 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.046 #=END data_Form_B #(1).(dioxane) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N2 O7 . C4 H8 O2' _chemical_formula_sum 'C11 H12 N2 O9' _chemical_formula_weight 316.23 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6852(8) _cell_length_b 9.7347(18) _cell_length_c 10.5534(18) _cell_angle_alpha 79.468(17) _cell_angle_beta 80.152(14) _cell_angle_gamma 82.990(12) _cell_volume 662.35(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description ? _exptl_crystal_colour Yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type none _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '90 minutes' _diffrn_standards_decay_% 14 _diffrn_reflns_number 3910 _diffrn_reflns_av_R_equivalents 0.0030 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 30.01 _reflns_number_total 3851 _reflns_number_gt 2088 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0708P] 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 3851 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1128 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1541 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.25502(19) 1.11850(9) 0.58860(9) 0.0440(4) Uani 1 1 d G . . C2 C 0.2377(2) 1.11058(9) 0.46080(11) 0.0441(4) Uani 1 1 d G . . C3 C 0.22888(19) 1.23216(11) 0.36863(8) 0.0432(4) Uani 1 1 d G . . C4 C 0.23733(19) 1.36167(9) 0.40427(10) 0.0439(4) Uani 1 1 d G . . H4A H 0.2314 1.4430 0.3426 0.061(4) Uiso 1 1 calc R . . C5 C 0.2546(2) 1.36960(9) 0.53208(11) 0.0443(4) Uani 1 1 d G . . C6 C 0.26347(19) 1.24802(12) 0.62424(8) 0.0462(4) Uani 1 1 d G . . H6A H 0.2750 1.2533 0.7098 0.061(4) Uiso 1 1 calc R . . C7 C 0.2674(3) 0.9897(2) 0.68699(19) 0.0501(5) Uani 1 1 d . . . C8 C 0.2368(3) 0.6626(2) -0.0337(2) 0.0560(5) Uani 1 1 d . . . H8A H 0.3198 0.5744 -0.0155 0.075(3) Uiso 1 1 calc R . . H8B H 0.1868 0.6654 -0.1152 0.075(3) Uiso 1 1 calc R . . C9 C 0.0617(4) 0.6715(2) 0.0733(2) 0.0592(5) Uani 1 1 d . . . H9A H -0.0253 0.7572 0.0524 0.075(3) Uiso 1 1 calc R . . H9B H -0.0183 0.5928 0.0812 0.075(3) Uiso 1 1 calc R . . C10 C 0.2478(4) 0.7852(2) 0.1822(2) 0.0683(7) Uani 1 1 d . . . H10A H 0.2957 0.7836 0.2642 0.075(3) Uiso 1 1 calc R . . H10B H 0.1628 0.8724 0.1636 0.075(3) Uiso 1 1 calc R . . C11 C 0.4248(4) 0.7797(3) 0.0770(2) 0.0677(6) Uani 1 1 d . . . H11A H 0.4996 0.8609 0.0692 0.075(3) Uiso 1 1 calc R . . H11B H 0.5156 0.6962 0.0988 0.075(3) Uiso 1 1 calc R . . O1 O 0.2805(3) 1.01027(16) 0.80378(14) 0.0655(4) Uani 1 1 d . . . H1A H 0.3054 0.9347 0.8498 0.091(7) Uiso 1 1 calc R . . O2 O 0.2678(3) 0.87375(15) 0.65883(14) 0.0653(4) Uani 1 1 d . . . O3 O 0.2337(2) 0.98489(14) 0.42554(13) 0.0564(4) Uani 1 1 d . . . H3A H 0.2429 0.9227 0.4888 0.091(7) Uiso 1 1 calc R . . O4 O 0.2122(3) 1.12441(17) 0.19484(15) 0.0870(6) Uani 1 1 d . . . O5 O 0.1969(3) 1.34543(17) 0.16122(16) 0.0882(6) Uani 1 1 d . . . O6 O 0.2526(3) 1.60935(15) 0.48870(16) 0.0710(5) Uani 1 1 d . . . O7 O 0.2869(3) 1.50479(17) 0.68200(16) 0.0822(6) Uani 1 1 d . . . O8 O 0.3583(2) 0.77745(16) -0.04506(13) 0.0635(4) Uani 1 1 d . . . O9 O 0.1302(2) 0.67020(16) 0.19374(13) 0.0637(4) Uani 1 1 d . . . N1 N 0.2107(3) 1.23367(18) 0.23260(16) 0.0540(4) Uani 1 1 d . . . N2 N 0.2645(3) 1.50338(18) 0.57038(17) 0.0535(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 0.0427(10) 0.0482(10) 0.0416(9) -0.0076(8) -0.0066(8) -0.0059(8) C2 0.0425(10) 0.0468(10) 0.0458(10) -0.0148(8) -0.0054(8) -0.0064(8) C3 0.0437(10) 0.0493(10) 0.0389(9) -0.0116(8) -0.0075(8) -0.0058(8) C4 0.0428(10) 0.0448(9) 0.0455(10) -0.0094(8) -0.0074(8) -0.0062(8) C5 0.0426(10) 0.0462(10) 0.0478(10) -0.0156(8) -0.0063(8) -0.0072(8) C6 0.0455(11) 0.0552(11) 0.0414(9) -0.0134(8) -0.0073(8) -0.0091(9) C7 0.0524(12) 0.0520(11) 0.0462(11) -0.0084(9) -0.0073(9) -0.0055(9) C8 0.0713(14) 0.0535(11) 0.0478(11) -0.0121(9) -0.0163(10) -0.0086(10) C9 0.0673(14) 0.0616(13) 0.0543(12) -0.0130(10) -0.0164(11) -0.0135(11) C10 0.0987(19) 0.0601(13) 0.0562(13) -0.0223(10) -0.0212(13) -0.0142(13) C11 0.0816(17) 0.0718(14) 0.0577(13) -0.0010(11) -0.0294(12) -0.0272(12) O1 0.0953(12) 0.0567(9) 0.0470(8) -0.0049(7) -0.0203(8) -0.0097(8) O2 0.0945(12) 0.0472(8) 0.0550(9) -0.0072(6) -0.0140(8) -0.0074(8) O3 0.0767(10) 0.0455(7) 0.0501(8) -0.0133(6) -0.0127(7) -0.0058(7) O4 0.1611(19) 0.0606(10) 0.0491(9) -0.0170(7) -0.0212(10) -0.0294(11) O5 0.1570(19) 0.0576(10) 0.0555(9) -0.0064(8) -0.0431(11) 0.0014(11) O6 0.0992(13) 0.0488(9) 0.0684(10) -0.0126(8) -0.0197(9) -0.0063(8) O7 0.1303(16) 0.0716(11) 0.0563(10) -0.0251(8) -0.0165(10) -0.0299(10) O8 0.0777(11) 0.0691(10) 0.0473(8) 0.0024(7) -0.0196(7) -0.0246(8) O9 0.0814(11) 0.0685(9) 0.0462(8) -0.0143(7) -0.0091(7) -0.0201(8) N1 0.0643(11) 0.0549(10) 0.0463(9) -0.0135(8) -0.0112(8) -0.0075(8) N2 0.0565(11) 0.0546(10) 0.0536(10) -0.0187(8) -0.0054(8) -0.0117(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 C2 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.478(2) . ? C2 O3 1.3469(15) . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C3 N1 1.4586(18) . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 N2 1.4444(18) . ? C7 O2 1.218(2) . ? C7 O1 1.303(2) . ? C8 O8 1.437(2) . ? C8 C9 1.487(3) . ? C9 O9 1.420(2) . ? C10 O9 1.421(3) . ? C10 C11 1.480(3) . ? C11 O8 1.437(2) . ? O4 N1 1.200(2) . ? O5 N1 1.208(2) . ? O6 N2 1.221(2) . ? O7 N2 1.215(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 C2 C1 C6 120.0 . . ? C2 C1 C7 120.45(10) . . ? C6 C1 C7 119.54(10) . . ? O3 C2 C3 119.94(9) . . ? O3 C2 C1 120.05(9) . . ? C3 C2 C1 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 N1 123.70(10) . . ? C4 C3 N1 116.30(10) . . ? C5 C4 C3 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 N2 119.39(10) . . ? C4 C5 N2 120.61(10) . . ? C5 C6 C1 120.0 . . ? O2 C7 O1 123.37(18) . . ? O2 C7 C1 121.67(16) . . ? O1 C7 C1 114.96(16) . . ? O8 C8 C9 110.00(16) . . ? O9 C9 C8 110.95(18) . . ? O9 C10 C11 111.24(17) . . ? O8 C11 C10 110.52(19) . . ? C8 O8 C11 110.56(15) . . ? C9 O9 C10 109.49(16) . . ? O4 N1 O5 122.18(18) . . ? O4 N1 C3 119.23(16) . . ? O5 N1 C3 118.59(15) . . ? O7 N2 O6 123.18(17) . . ? O7 N2 C5 118.32(16) . . ? O6 N2 C5 118.48(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.300 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.043 #=END data_Form_C #(1).(dioxane) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N2 O7 . C4 H8 O2' _chemical_formula_sum 'C11 H12 N2 O9' _chemical_formula_weight 316.23 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.149(15) _cell_length_b 11.912(3) _cell_length_c 13.318(4) _cell_angle_alpha 111.22(3) _cell_angle_beta 90.13(6) _cell_angle_gamma 101.12(4) _cell_volume 1323(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description ? _exptl_crystal_colour Yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type none _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '90 minutes' _diffrn_standards_decay_% 13 _diffrn_reflns_number 6384 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 28.07 _reflns_number_total 6384 _reflns_number_gt 3316 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0960P)^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 6384 _refine_ls_number_parameters 436 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1169 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.1883 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.002 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3718(2) 0.30194(18) 0.50258(17) 0.0720(6) Uani 1 1 d . . . H7A H 0.3943 0.2353 0.4913 0.108 Uiso 1 1 calc R . . O2 O 0.2258(3) 0.19512(17) 0.35011(17) 0.0699(6) Uani 1 1 d . . . O3 O 0.0645(2) 0.30633(17) 0.27900(15) 0.0661(6) Uani 1 1 d . . . H2A H 0.0994 0.2487 0.2811 0.099 Uiso 1 1 calc R . . O4 O -0.1250(4) 0.4345(3) 0.2527(3) 0.0806(9) Uani 0.78 1 d P . . O4A O -0.0272(16) 0.4686(14) 0.2066(8) 0.091(4) Uani 0.22 1 d P . . O5 O -0.0806(10) 0.6185(9) 0.3297(7) 0.091(3) Uani 0.34 1 d P . . O5A O -0.0027(5) 0.6121(4) 0.2718(4) 0.0860(13) Uani 0.66 1 d P . . O6 O 0.2377(3) 0.82002(18) 0.64786(17) 0.0780(7) Uani 1 1 d . . . O7 O 0.4029(3) 0.7355(2) 0.68577(19) 0.0939(8) Uani 1 1 d . . . O8 O 0.0279(2) 0.31067(18) 1.00224(17) 0.0700(6) Uani 1 1 d . . . H6A H -0.0296 0.2450 0.9924 0.105 Uiso 1 1 calc R . . O9 O 0.1121(2) 0.19895(18) 0.84943(17) 0.0691(6) Uani 1 1 d . . . O10 O 0.3293(2) 0.30413(17) 0.77425(15) 0.0647(5) Uani 1 1 d . . . H3A H 0.2640 0.2482 0.7779 0.097 Uiso 1 1 calc R . . O11 O 0.5895(4) 0.4241(3) 0.7493(3) 0.0762(10) Uani 0.68 1 d P . . O11A O 0.5154(11) 0.4524(9) 0.7024(6) 0.095(3) Uani 0.32 1 d P . . O12 O 0.6465(7) 0.6073(7) 0.8232(5) 0.089(2) Uani 0.43 1 d P . . O12A O 0.5676(6) 0.6051(5) 0.7682(4) 0.0813(14) Uani 0.57 1 d P . . O13 O 0.4428(3) 0.81932(19) 1.14258(17) 0.0759(6) Uani 1 1 d . . . O14 O 0.2314(3) 0.7412(2) 1.18194(18) 0.0815(7) Uani 1 1 d . . . O15 O 0.4632(2) 0.10333(16) 0.48876(15) 0.0601(5) Uani 1 1 d . . . O17 O 0.0599(3) 0.90004(19) 0.49711(17) 0.0806(7) Uani 1 1 d . . . O18 O 0.3357(3) 1.10111(19) 0.00240(17) 0.0827(7) Uani 1 1 d . . . O19 O 0.1637(2) 0.88624(18) 0.01175(16) 0.0740(6) Uani 1 1 d . . . N1 N -0.0245(3) 0.5245(2) 0.2961(2) 0.0572(6) Uani 1 1 d . . . N2 N 0.2988(3) 0.7341(2) 0.63021(19) 0.0613(6) Uani 1 1 d . . . N3 N 0.5388(3) 0.5177(2) 0.79210(19) 0.0552(6) Uani 1 1 d . . . N4 N 0.3345(3) 0.7359(2) 1.12556(19) 0.0576(6) Uani 1 1 d . . . C1 C 0.22920(18) 0.40737(11) 0.43836(12) 0.0454(6) Uani 1 1 d G . . C2 C 0.12597(18) 0.40878(11) 0.36230(10) 0.0433(6) Uani 1 1 d G . . C3 C 0.08159(16) 0.51763(14) 0.37346(11) 0.0440(6) Uani 1 1 d G . . C4 C 0.14044(18) 0.62507(11) 0.46068(12) 0.0455(6) Uani 1 1 d G . . H4 H 0.1108 0.6979 0.4681 0.055 Uiso 1 1 calc . . . C5 C 0.24367(18) 0.62366(11) 0.53673(11) 0.0466(6) Uani 1 1 d G . . C6 C 0.28805(16) 0.51481(14) 0.52557(11) 0.0484(6) Uani 1 1 d G . . H6 H 0.3571 0.5139 0.5765 0.058 Uiso 1 1 calc . . . C7 C 0.2750(3) 0.2910(3) 0.4256(2) 0.0535(7) Uani 1 1 d . . . C8 C 0.22345(15) 0.41002(11) 0.93483(13) 0.0445(6) Uani 1 1 d G . . C9 C 0.32659(18) 0.40776(11) 0.85802(10) 0.0453(6) Uani 1 1 d G . . C10 C 0.43017(16) 0.51412(14) 0.86835(11) 0.0438(6) Uani 1 1 d G . . C11 C 0.43059(16) 0.62274(11) 0.95548(13) 0.0470(6) Uani 1 1 d G . . H11 H 0.4999 0.6939 0.9624 0.056 Uiso 1 1 calc . . . C12 C 0.32745(18) 0.62501(11) 1.03229(11) 0.0460(6) Uani 1 1 d G . . C13 C 0.22388(16) 0.51865(14) 1.02197(11) 0.0485(6) Uani 1 1 d G . . H13 H 0.1549 0.5202 1.0734 0.058 Uiso 1 1 calc . . . C14 C 0.1161(3) 0.2965(3) 0.9242(2) 0.0531(7) Uani 1 1 d . . . C15 C 0.5640(4) 0.1160(3) 0.5770(2) 0.0630(8) Uani 1 1 d . . . H36A H 0.5538 0.1870 0.6397 0.076 Uiso 1 1 calc R . . H36B H 0.6661 0.1290 0.5574 0.076 Uiso 1 1 calc R . . C16 C 0.4700(4) -0.0025(2) 0.3961(2) 0.0609(8) Uani 1 1 d . . . H30A H 0.5690 0.0063 0.3701 0.073 Uiso 1 1 calc R . . H30B H 0.3984 -0.0098 0.3390 0.073 Uiso 1 1 calc R . . C18 C 0.0503(5) 0.9334(4) 0.4036(3) 0.0674(10) Uani 0.85 1 d P . . H18A H 0.1429 0.9876 0.4011 0.081 Uiso 0.85 1 calc P . . H18B H 0.0360 0.8600 0.3385 0.081 Uiso 0.85 1 calc P . . C18A C 0.062(3) 1.1137(19) 0.584(2) 0.076(7) Uani 0.15 1 d P . . C17 C 0.0719(5) 1.0057(3) 0.5918(3) 0.0858(11) Uani 1 1 d . . . H42A H 0.1649 1.0626 0.5949 0.103 Uiso 1 1 calc R . . H42B H 0.0750 0.9824 0.6542 0.103 Uiso 1 1 calc R . . C19 C 0.2849(5) 0.9955(3) -0.0915(3) 0.1024(14) Uani 1 1 d . . . H19A H 0.3571 0.9931 -0.1451 0.123 Uiso 1 1 calc . . . H19B H 0.1914 1.0022 -0.1211 0.123 Uiso 1 1 calc . . . C20 C 0.2628(7) 0.8831(5) -0.0729(5) 0.0639(15) Uani 0.70 1 d P . . H20A H 0.3582 0.8701 -0.0526 0.077 Uiso 0.70 1 calc P . . H20B H 0.2206 0.8150 -0.1389 0.077 Uiso 0.70 1 calc P . . C20A C 0.185(2) 0.9098(16) -0.0882(13) 0.098(6) Uani 0.30 1 d P . . C21 C 0.2098(5) 0.9941(3) 0.1052(3) 0.0872(11) Uani 1 1 d . . . H21A H 0.3022 0.9899 0.1382 0.105 Uiso 1 1 calc . . . H21B H 0.1347 0.9972 0.1570 0.105 Uiso 1 1 calc . . . C22 C 0.2322(7) 1.1046(4) 0.0825(4) 0.0708(14) Uani 0.70 1 d P . . H22A H 0.1374 1.1143 0.0575 0.085 Uiso 0.70 1 calc P . . H22B H 0.2695 1.1748 0.1482 0.085 Uiso 0.70 1 calc P . . C22A C 0.3273(18) 1.0787(12) 0.1093(9) 0.092(5) Uani 0.30 1 d P . . 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 0.0882(15) 0.0623(13) 0.0769(14) 0.0276(11) -0.0017(12) 0.0386(11) O2 0.0933(16) 0.0450(11) 0.0697(14) 0.0147(11) 0.0048(12) 0.0235(11) O3 0.0762(14) 0.0524(11) 0.0592(12) 0.0093(10) -0.0061(10) 0.0113(10) O4 0.072(2) 0.074(2) 0.089(2) 0.0323(18) -0.0325(19) -0.0040(16) O4A 0.116(10) 0.135(11) 0.031(5) 0.020(6) -0.004(6) 0.069(9) O5 0.106(7) 0.099(6) 0.086(6) 0.038(5) -0.015(5) 0.055(6) O5A 0.101(3) 0.077(3) 0.097(3) 0.059(3) -0.028(2) 0.002(2) O6 0.1113(19) 0.0458(11) 0.0686(14) 0.0071(10) 0.0013(13) 0.0249(12) O7 0.0896(18) 0.0945(18) 0.0724(16) -0.0017(13) -0.0284(14) 0.0255(15) O8 0.0650(13) 0.0599(12) 0.0770(14) 0.0250(11) 0.0092(11) -0.0054(10) O9 0.0734(14) 0.0484(11) 0.0737(14) 0.0151(11) 0.0005(11) 0.0002(10) O10 0.0697(13) 0.0518(11) 0.0597(12) 0.0070(10) 0.0087(10) 0.0097(10) O11 0.082(3) 0.067(2) 0.084(3) 0.025(2) 0.036(2) 0.0310(19) O11A 0.095(6) 0.110(7) 0.051(5) 0.008(5) 0.015(4) -0.006(5) O12 0.080(4) 0.090(4) 0.076(4) 0.023(4) 0.026(3) -0.017(4) O12A 0.104(4) 0.075(3) 0.087(4) 0.052(3) 0.042(3) 0.027(3) O13 0.0873(16) 0.0532(12) 0.0644(14) 0.0049(10) 0.0050(12) -0.0051(12) O14 0.0792(15) 0.0789(15) 0.0654(14) 0.0028(12) 0.0240(12) 0.0147(12) O15 0.0815(14) 0.0467(10) 0.0581(12) 0.0173(9) -0.0037(10) 0.0319(10) O17 0.120(2) 0.0619(13) 0.0650(13) 0.0135(11) -0.0020(13) 0.0519(13) O18 0.1080(18) 0.0541(12) 0.0637(14) 0.0132(11) 0.0236(13) -0.0179(12) O19 0.0870(15) 0.0547(12) 0.0615(13) 0.0152(10) 0.0132(11) -0.0160(11) N1 0.0595(15) 0.0680(16) 0.0534(15) 0.0301(13) -0.0001(12) 0.0199(14) N2 0.0674(16) 0.0549(15) 0.0534(14) 0.0129(12) 0.0007(12) 0.0080(13) N3 0.0559(15) 0.0621(15) 0.0499(15) 0.0231(13) 0.0070(12) 0.0124(13) N4 0.0656(16) 0.0542(14) 0.0472(13) 0.0112(11) 0.0043(12) 0.0138(12) C1 0.0486(14) 0.0465(14) 0.0461(14) 0.0197(12) 0.0080(11) 0.0163(11) C2 0.0485(14) 0.0425(13) 0.0365(13) 0.0123(11) 0.0075(11) 0.0088(11) C3 0.0461(14) 0.0512(14) 0.0414(13) 0.0243(12) 0.0056(11) 0.0111(11) C4 0.0499(15) 0.0450(14) 0.0492(15) 0.0238(12) 0.0106(12) 0.0149(11) C5 0.0507(15) 0.0424(14) 0.0430(14) 0.0114(11) 0.0032(11) 0.0095(11) C6 0.0475(15) 0.0526(15) 0.0479(14) 0.0194(12) 0.0024(11) 0.0155(12) C7 0.0617(17) 0.0526(16) 0.0561(17) 0.0255(14) 0.0134(14) 0.0241(13) C8 0.0417(13) 0.0457(14) 0.0452(14) 0.0173(12) -0.0019(11) 0.0056(11) C9 0.0516(15) 0.0432(14) 0.0385(13) 0.0107(11) -0.0058(11) 0.0127(11) C10 0.0422(13) 0.0509(14) 0.0431(14) 0.0219(12) 0.0003(11) 0.0113(11) C11 0.0489(15) 0.0455(14) 0.0492(15) 0.0218(12) -0.0040(12) 0.0074(11) C12 0.0507(15) 0.0427(14) 0.0409(13) 0.0109(11) -0.0009(11) 0.0101(11) C13 0.0454(14) 0.0556(15) 0.0463(14) 0.0204(12) 0.0025(11) 0.0112(12) C14 0.0478(15) 0.0548(17) 0.0549(17) 0.0215(14) -0.0037(13) 0.0040(12) C15 0.077(2) 0.0502(16) 0.0588(18) 0.0144(14) -0.0077(15) 0.0163(14) C16 0.080(2) 0.0577(17) 0.0491(16) 0.0174(14) -0.0035(14) 0.0282(15) C18 0.084(3) 0.061(2) 0.060(2) 0.0163(19) 0.006(2) 0.034(2) C18A 0.081(16) 0.054(12) 0.094(17) 0.036(12) -0.031(14) -0.003(11) C17 0.123(3) 0.075(2) 0.060(2) 0.0116(18) -0.007(2) 0.051(2) C19 0.142(4) 0.067(2) 0.069(2) 0.0128(19) 0.023(2) -0.023(2) C20 0.087(4) 0.045(2) 0.053(3) 0.014(2) 0.016(3) 0.008(3) C20A 0.122(15) 0.088(12) 0.054(7) 0.023(8) 0.001(9) -0.041(10) C21 0.115(3) 0.066(2) 0.059(2) 0.0153(17) 0.0202(19) -0.014(2) C22 0.095(4) 0.052(3) 0.063(3) 0.018(2) 0.019(3) 0.015(3) C22A 0.128(12) 0.069(8) 0.048(6) 0.020(6) -0.001(7) -0.048(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 O1 C7 1.306(3) . ? O2 C7 1.220(3) . ? O3 C2 1.337(2) . ? O4 O4A 1.178(14) . ? O4 N1 1.224(4) . ? O4A N1 1.133(10) . ? O4A O5A 1.582(14) . ? O5 O5A 1.043(9) . ? O5 N1 1.255(8) . ? O5A N1 1.182(4) . ? O6 N2 1.209(3) . ? O7 N2 1.199(3) . ? O8 C14 1.300(3) . ? O9 C14 1.220(3) . ? O10 C9 1.336(2) . ? O11 O11A 1.096(10) . ? O11 N3 1.235(4) . ? O11A N3 1.157(8) . ? O11A O12A 1.677(11) . ? O12 O12A 1.017(7) . ? O12 N3 1.247(6) . ? O12A N3 1.178(5) . ? O13 N4 1.215(3) . ? O14 N4 1.204(3) . ? O15 C16 1.421(3) . ? O15 C15 1.437(3) . ? O17 C17 1.408(4) . ? O17 C18 1.444(4) . ? O17 C18A 1.49(2) 2_576 ? O18 C19 1.413(4) . ? O18 C22 1.423(6) . ? O18 C22A 1.540(12) . ? O19 C21 1.417(4) . ? O19 C20 1.443(7) . ? O19 C20A 1.463(16) . ? N1 C3 1.448(3) . ? N2 C5 1.446(3) . ? N3 C10 1.429(3) . ? N4 C12 1.439(3) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.476(3) . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C8 C9 1.3900 . ? C8 C13 1.3900 . ? C8 C14 1.470(3) . ? C9 C10 1.3900 . ? C10 C11 1.3900 . ? C11 C12 1.3900 . ? C12 C13 1.3900 . ? C15 C16 1.498(4) 2_656 ? C16 C15 1.498(4) 2_656 ? C18 C17 1.436(5) 2_576 ? C18A C18 1.12(3) 2_576 ? C18A O17 1.49(2) 2_576 ? C17 C18 1.436(5) 2_576 ? C19 C20 1.426(7) . ? C21 C22 1.432(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 O4A O4 N1 56.3(6) . . ? N1 O4A O4 63.9(6) . . ? N1 O4A O5A 48.2(6) . . ? O4 O4A O5A 99.3(8) . . ? O5A O5 N1 61.1(5) . . ? O5 O5A N1 68.3(5) . . ? O5 O5A O4A 103.0(8) . . ? N1 O5A O4A 45.6(4) . . ? O11A O11 N3 59.2(5) . . ? O11 O11A N3 66.4(5) . . ? O11 O11A O12A 98.0(6) . . ? N3 O11A O12A 44.6(4) . . ? O12A O12 N3 61.7(5) . . ? O12 O12A N3 68.8(5) . . ? O12 O12A O11A 99.7(7) . . ? N3 O12A O11A 43.6(4) . . ? C16 O15 C15 111.7(2) . . ? C17 O17 C18 109.5(3) . . ? C17 O17 C18A 113.6(10) . 2_576 ? C18 O17 C18A 44.7(10) . 2_576 ? C19 O18 C22 109.5(3) . . ? C19 O18 C22A 115.1(5) . . ? C22 O18 C22A 42.4(6) . . ? C21 O19 C20 111.6(3) . . ? C21 O19 C20A 112.5(7) . . ? C20 O19 C20A 35.4(7) . . ? O4A N1 O5A 86.2(8) . . ? O4A N1 O4 59.8(8) . . ? O5A N1 O4 123.4(3) . . ? O4A N1 O5 121.2(7) . . ? O5A N1 O5 50.6(4) . . ? O4 N1 O5 108.5(5) . . ? O4A N1 C3 121.5(6) . . ? O5A N1 C3 118.4(3) . . ? O4 N1 C3 117.8(2) . . ? O5 N1 C3 114.4(4) . . ? O7 N2 O6 123.6(3) . . ? O7 N2 C5 118.1(2) . . ? O6 N2 C5 118.3(2) . . ? O11A N3 O12A 91.8(6) . . ? O11A N3 O11 54.4(5) . . ? O12A N3 O11 123.7(3) . . ? O11A N3 O12 122.0(5) . . ? O12A N3 O12 49.5(4) . . ? O11 N3 O12 107.6(5) . . ? O11A N3 C10 121.0(5) . . ? O12A N3 C10 119.0(3) . . ? O11 N3 C10 117.1(3) . . ? O12 N3 C10 116.0(3) . . ? O14 N4 O13 123.6(3) . . ? O14 N4 C12 117.9(2) . . ? O13 N4 C12 118.5(2) . . ? C2 C1 C6 120.0 . . ? C2 C1 C7 119.41(16) . . ? C6 C1 C7 120.59(16) . . ? O3 C2 C3 118.56(14) . . ? O3 C2 C1 121.42(14) . . ? C3 C2 C1 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 N1 117.71(15) . . ? C2 C3 N1 122.28(15) . . ? C3 C4 C5 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 N2 120.14(15) . . ? C4 C5 N2 119.78(15) . . ? C5 C6 C1 120.0 . . ? O2 C7 O1 124.3(3) . . ? O2 C7 C1 122.3(2) . . ? O1 C7 C1 113.4(2) . . ? C9 C8 C13 120.0 . . ? C9 C8 C14 119.56(16) . . ? C13 C8 C14 120.44(16) . . ? O10 C9 C10 118.96(15) . . ? O10 C9 C8 121.04(14) . . ? C10 C9 C8 120.0 . . ? C11 C10 C9 120.0 . . ? C11 C10 N3 117.35(15) . . ? C9 C10 N3 122.65(15) . . ? C10 C11 C12 120.0 . . ? C11 C12 C13 120.0 . . ? C11 C12 N4 119.57(15) . . ? C13 C12 N4 120.33(15) . . ? C12 C13 C8 120.0 . . ? O9 C14 O8 123.9(3) . . ? O9 C14 C8 122.7(3) . . ? O8 C14 C8 113.4(2) . . ? O15 C15 C16 110.0(2) . 2_656 ? O15 C16 C15 110.4(2) . 2_656 ? C17 C18 O17 110.4(3) 2_576 . ? C18 C18A O17 65.3(12) 2_576 2_576 ? O17 C17 C18 112.3(3) . 2_576 ? O18 C19 C20 113.6(4) . . ? C19 C20 O19 110.6(4) . . ? O19 C21 C22 112.9(3) . . ? O18 C22 C21 111.0(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.354 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.045 #=END data_Form_D #(1).(dioxane)0.5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N2 O7 . C4 H8 O2' _chemical_formula_sum 'C9 H4 N2 O8' _chemical_formula_weight 268.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 11.3053(10) _cell_length_b 6.0266(5) _cell_length_c 16.9126(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.921(9) _cell_angle_gamma 90.00 _cell_volume 1141.30(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 22 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type none _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '90 minutes' _diffrn_standards_decay_% 10 _diffrn_reflns_number 2936 _diffrn_reflns_av_R_equivalents 0.0119 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.92 _reflns_number_total 2734 _reflns_number_gt 1446 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Highly disordered Carbon atoms of the dioxane molecule was refined using EADP instruction in SHELXL-97. ; _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^)+(0.1370P)^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 2734 _refine_ls_number_parameters 184 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1348 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.2424 _refine_ls_wR_factor_gt 0.2114 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -1.08900(13) 0.0461(3) 0.67065(12) 0.0487(7) Uani 1 1 d G . . C2 C -1.03078(15) -0.0812(3) 0.61933(11) 0.0461(7) Uani 1 1 d G . . C3 C -0.91935(15) -0.0163(3) 0.60170(10) 0.0440(7) Uani 1 1 d G . . C4 C -0.86613(13) 0.1757(3) 0.63539(11) 0.0470(7) Uani 1 1 d G . . H4A H -0.7916 0.2191 0.6236 0.056 Uiso 1 1 calc R . . C5 C -0.92435(16) 0.3030(3) 0.68670(11) 0.0478(7) Uani 1 1 d G . . C6 C -1.03578(16) 0.2382(3) 0.70434(11) 0.0517(8) Uani 1 1 d G . . H6A H -1.0747 0.3233 0.7387 0.062 Uiso 1 1 calc R . . N1 N -1.2036(3) -0.0127(6) 0.6920(2) 0.0677(9) Uani 1 1 d . . . O5 O -1.2123(3) -0.0235(7) 0.7631(2) 0.1151(14) Uani 1 1 d . . . O4 O -1.2844(3) -0.0416(6) 0.6403(2) 0.0961(11) Uani 1 1 d . . . O3 O -1.08622(19) -0.2667(4) 0.58992(13) 0.0594(7) Uani 1 1 d . . . H3A H -1.0436 -0.3326 0.5622 0.089 Uiso 1 1 calc R . . O2 O -0.89655(19) -0.3320(4) 0.52168(13) 0.0599(7) Uani 1 1 d . . . O1 O -0.7452(2) -0.0914(5) 0.54681(15) 0.0703(8) Uani 1 1 d . . . H1A H -0.7057 -0.1914 0.5306 0.105 Uiso 1 1 calc R . . O7 O -0.7788(2) 0.5687(4) 0.69801(15) 0.0705(8) Uani 1 1 d . . . O6 O -0.9187(3) 0.5990(5) 0.77207(19) 0.0888(10) Uani 1 1 d . . . C7 C -0.8536(3) -0.1647(6) 0.55256(18) 0.0508(8) Uani 1 1 d . . . N2 N -0.8703(3) 0.5040(5) 0.72147(17) 0.0584(7) Uani 1 1 d . . . O8 O -0.5953(2) -0.3607(5) 0.4985(2) 0.1013(12) Uani 1 1 d . . . C8A C -0.524(2) -0.480(5) 0.5833(14) 0.0638(17) Uani 0.202(11) 1 d P . . C8B C -0.539(2) -0.396(5) 0.4259(14) 0.0638(17) Uani 0.175(9) 1 d P . . C8C C -0.594(3) -0.477(6) 0.436(2) 0.0638(17) Uani 0.151(11) 1 d P . . C9A C -0.5842(19) -0.546(4) 0.5510(15) 0.0638(17) Uani 0.182(9) 1 d P . . C9B C -0.6135(9) -0.578(3) 0.4620(11) 0.0638(17) Uani 0.390(12) 1 d P . . C9C C -0.4906(12) -0.303(3) 0.4528(11) 0.0638(17) Uani 0.279(9) 1 d P . . C8D C -0.6104(15) -0.620(3) 0.5062(17) 0.0638(17) Uani 0.231(11) 1 d P . . C9D C -0.4946(15) -0.387(4) 0.5713(11) 0.0638(17) Uani 0.232(12) 1 d P . . C9E C -0.4752(19) -0.272(4) 0.5040(17) 0.0638(17) Uani 0.159(8) 1 d P . . 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 0.0433(15) 0.0483(18) 0.0561(17) 0.0021(14) 0.0130(13) 0.0009(14) C2 0.0492(16) 0.0412(15) 0.0473(16) 0.0039(13) 0.0038(13) 0.0017(13) C3 0.0424(15) 0.0445(16) 0.0453(15) 0.0039(13) 0.0071(12) 0.0059(13) C4 0.0420(15) 0.0508(17) 0.0475(16) 0.0100(14) 0.0038(12) 0.0024(14) C5 0.0458(16) 0.0439(17) 0.0516(16) 0.0037(13) -0.0006(13) 0.0025(13) C6 0.0572(18) 0.0445(17) 0.0550(17) -0.0015(14) 0.0134(14) 0.0075(14) N1 0.0582(18) 0.069(2) 0.080(2) -0.0100(17) 0.0250(17) -0.0065(16) O5 0.116(3) 0.149(3) 0.091(2) -0.006(2) 0.053(2) -0.045(2) O4 0.0576(16) 0.127(3) 0.105(2) -0.017(2) 0.0170(16) -0.0118(18) O3 0.0565(13) 0.0500(13) 0.0735(15) -0.0135(11) 0.0154(11) -0.0054(11) O2 0.0552(13) 0.0618(15) 0.0624(14) -0.0138(11) 0.0071(11) 0.0066(11) O1 0.0568(14) 0.0674(16) 0.0921(18) -0.0109(13) 0.0297(13) 0.0041(12) O7 0.0679(16) 0.0616(16) 0.0785(17) 0.0015(13) -0.0021(13) -0.0158(13) O6 0.089(2) 0.0768(19) 0.101(2) -0.0425(17) 0.0170(17) -0.0081(16) C7 0.0455(16) 0.0552(19) 0.0517(17) 0.0042(15) 0.0063(13) 0.0085(15) N2 0.0565(17) 0.0504(16) 0.0642(17) -0.0015(14) -0.0061(14) -0.0035(14) O8 0.0597(17) 0.091(2) 0.158(3) -0.009(2) 0.0304(18) 0.0237(16) C8A 0.046(3) 0.071(5) 0.077(5) -0.013(4) 0.016(3) -0.005(3) C8B 0.046(3) 0.071(5) 0.077(5) -0.013(4) 0.016(3) -0.005(3) C8C 0.046(3) 0.071(5) 0.077(5) -0.013(4) 0.016(3) -0.005(3) C9A 0.046(3) 0.071(5) 0.077(5) -0.013(4) 0.016(3) -0.005(3) C9B 0.046(3) 0.071(5) 0.077(5) -0.013(4) 0.016(3) -0.005(3) C9C 0.046(3) 0.071(5) 0.077(5) -0.013(4) 0.016(3) -0.005(3) C8D 0.046(3) 0.071(5) 0.077(5) -0.013(4) 0.016(3) -0.005(3) C9D 0.046(3) 0.071(5) 0.077(5) -0.013(4) 0.016(3) -0.005(3) C9E 0.046(3) 0.071(5) 0.077(5) -0.013(4) 0.016(3) -0.005(3) _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 1.3900 . ? C1 C6 1.3900 . ? C1 N1 1.437(3) . ? C2 O3 1.343(3) . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C3 C7 1.488(3) . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 N2 1.445(3) . ? N1 O4 1.187(4) . ? N1 O5 1.221(4) . ? O2 C7 1.207(4) . ? O1 C7 1.318(4) . ? O7 N2 1.221(4) . ? O6 N2 1.220(4) . ? O8 C8C 1.26(3) . ? O8 C9A 1.42(2) . ? O8 C9B 1.448(12) . ? O8 C9E 1.45(2) . ? O8 C8B 1.48(2) . ? O8 C9C 1.539(13) . ? O8 C9D 1.566(18) . ? O8 C8D 1.58(2) . ? O8 C8A 1.70(2) . ? C8A C9D 0.70(2) . ? C8A C9A 0.90(3) . ? C8A C8B 1.06(3) 3_446 ? C8A C8C 1.44(4) 3_446 ? C8A C9C 1.46(3) 3_446 ? C8A C8D 1.74(3) . ? C8A C9B 1.86(3) 3_446 ? C8A C9E 1.97(4) . ? C8B C8C 0.83(4) . ? C8B C9C 0.87(3) . ? C8B C8A 1.06(3) 3_446 ? C8B C9D 1.36(3) 3_446 ? C8B C9A 1.43(3) 3_446 ? C8B C9B 1.56(3) . ? C8B C9E 1.60(4) . ? C8B C8D 1.91(3) 3_446 ? C8C C9B 0.80(4) . ? C8C C9D 1.31(3) 3_446 ? C8C C8A 1.44(4) 3_446 ? C8C C8D 1.50(5) . ? C8C C9C 1.56(4) . ? C8C C9E 1.93(5) 3_446 ? C8C C9A 1.97(4) . ? C8C C9A 2.00(4) 3_446 ? C9A C8D 0.89(3) . ? C9A C9C 1.25(2) 3_446 ? C9A C9D 1.40(3) . ? C9A C8B 1.43(3) 3_446 ? C9A C9B 1.51(3) . ? C9A C9E 1.64(3) 3_446 ? C9A C8C 2.00(4) 3_446 ? C9B C8D 0.79(2) . ? C9B C9E 1.41(3) 3_446 ? C9B C9D 1.43(2) 3_446 ? C9B C8A 1.86(3) 3_446 ? C9B C9C 1.87(2) 3_446 ? C9C C9E 0.88(2) . ? C9C C9A 1.25(2) 3_446 ? C9C C8D 1.33(3) 3_446 ? C9C C8A 1.46(3) 3_446 ? C9C C9B 1.87(2) 3_446 ? C9C C9D 1.91(3) 3_446 ? C8D C9E 1.20(3) 3_446 ? C8D C9C 1.33(3) 3_446 ? C8D C9D 1.89(3) 3_446 ? C8D C8B 1.91(3) 3_446 ? C9D C8C 1.31(3) 3_446 ? C9D C8B 1.36(3) 3_446 ? C9D C9E 1.38(4) . ? C9D C9B 1.43(2) 3_446 ? C9D C8D 1.89(3) 3_446 ? C9D C9C 1.91(3) 3_446 ? C9E C8D 1.20(3) 3_446 ? C9E C9B 1.42(3) 3_446 ? C9E C9A 1.64(3) 3_446 ? C9E C8C 1.93(5) 3_446 ? 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 C6 120.0 . . ? C2 C1 N1 122.82(18) . . ? C6 C1 N1 117.18(17) . . ? O3 C2 C1 116.97(15) . . ? O3 C2 C3 123.02(15) . . ? C1 C2 C3 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 C7 120.54(17) . . ? C2 C3 C7 119.24(18) . . ? C5 C4 C3 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 N2 120.43(18) . . ? C6 C5 N2 119.57(17) . . ? C5 C6 C1 120.0 . . ? O4 N1 O5 124.0(3) . . ? O4 N1 C1 118.7(3) . . ? O5 N1 C1 117.3(3) . . ? O2 C7 O1 124.8(3) . . ? O2 C7 C3 122.8(3) . . ? O1 C7 C3 112.4(3) . . ? O6 N2 O7 124.0(3) . . ? O6 N2 C5 118.2(3) . . ? O7 N2 C5 117.7(3) . . ? C8C O8 C9A 94(2) . . ? C8C O8 C9B 33.3(17) . . ? C9A O8 C9B 63.4(12) . . ? C8C O8 C9E 97.9(19) . . ? C9A O8 C9E 104.5(14) . . ? C9B O8 C9E 116.0(11) . . ? C8C O8 C8B 34.0(17) . . ? C9A O8 C8B 113.2(14) . . ? C9B O8 C8B 64.3(13) . . ? C9E O8 C8B 66.3(15) . . ? C8C O8 C9C 66.9(19) . . ? C9A O8 C9C 118.9(9) . . ? C9B O8 C9C 93.7(9) . . ? C9E O8 C9C 34.0(10) . . ? C8B O8 C9C 33.3(10) . . ? C8C O8 C9D 120.4(14) . . ? C9A O8 C9D 55.7(13) . . ? C9B O8 C9D 106.7(10) . . ? C9E O8 C9D 54.2(14) . . ? C8B O8 C9D 106.8(12) . . ? C9C O8 C9D 83.8(10) . . ? C8C O8 C8D 62(2) . . ? C9A O8 C8D 34.2(11) . . ? C9B O8 C8D 29.7(8) . . ? C9E O8 C8D 118.2(12) . . ? C8B O8 C8D 89.4(14) . . ? C9C O8 C8D 111.4(9) . . ? C9D O8 C8D 84.8(12) . . ? C8C O8 C8A 114.1(18) . . ? C9A O8 C8A 32.0(12) . . ? C9B O8 C8A 90.0(12) . . ? C9E O8 C8A 76.9(14) . . ? C8B O8 C8A 115.5(11) . . ? C9C O8 C8A 102.2(10) . . ? C9D O8 C8A 24.1(8) . . ? C8D O8 C8A 63.7(13) . . ? C9D C8A C9A 122(4) . . ? C9D C8A C8B 99(3) . 3_446 ? C9A C8A C8B 94(3) . 3_446 ? C9D C8A C8C 65(3) . 3_446 ? C9A C8A C8C 115(2) . 3_446 ? C8B C8A C8C 34.4(19) 3_446 3_446 ? C9D C8A C9C 121(3) . 3_446 ? C9A C8A C9C 58(2) . 3_446 ? C8B C8A C9C 35.9(17) 3_446 3_446 ? C8C C8A C9C 65.1(17) 3_446 3_446 ? C9D C8A O8 67(3) . . ? C9A C8A O8 56(2) . . ? C8B C8A O8 115(2) 3_446 . ? C8C C8A O8 103(2) 3_446 . ? C9C C8A O8 95.3(14) 3_446 . ? C9D C8A C8D 114(3) . . ? C9A C8A C8D 14.9(16) . . ? C8B C8A C8D 82(2) 3_446 . ? C8C C8A C8D 100.4(17) 3_446 . ? C9C C8A C8D 48.4(11) 3_446 . ? O8 C8A C8D 54.6(11) . . ? C9D C8A C9B 43(2) . 3_446 ? C9A C8A C9B 116(2) . 3_446 ? C8B C8A C9B 56.8(19) 3_446 3_446 ? C8C C8A C9B 23.9(16) 3_446 3_446 ? C9C C8A C9B 81.0(11) 3_446 3_446 ? O8 C8A C9B 84.1(12) . 3_446 ? C8D C8A C9B 101.3(12) . 3_446 ? C9D C8A C9E 26(2) . . ? C9A C8A C9E 97(3) . . ? C8B C8A C9E 95(2) 3_446 . ? C8C C8A C9E 67(2) 3_446 . ? C9C C8A C9E 103.0(14) 3_446 . ? O8 C8A C9E 45.7(10) . . ? C8D C8A C9E 88.8(16) . . ? C9B C8A C9E 43.2(10) 3_446 . ? C8C C8B C9C 135(4) . . ? C8C C8B C8A 99(4) . 3_446 ? C9C C8B C8A 99(3) . 3_446 ? C8C C8B C9D 69(3) . 3_446 ? C9C C8B C9D 117(3) . 3_446 ? C8A C8B C9D 30.4(15) 3_446 3_446 ? C8C C8B C9A 122(3) . 3_446 ? C9C C8B C9A 60(2) . 3_446 ? C8A C8B C9A 38.9(17) 3_446 3_446 ? C9D C8B C9A 60.2(16) 3_446 3_446 ? C8C C8B O8 59(2) . . ? C9C C8B O8 77.4(19) . . ? C8A C8B O8 127(2) 3_446 . ? C9D C8B O8 105.2(19) 3_446 . ? C9A C8B O8 108.9(18) 3_446 . ? C8C C8B C9B 16(2) . . ? C9C C8B C9B 126(3) . . ? C8A C8B C9B 89(2) 3_446 . ? C9D C8B C9B 58.3(15) 3_446 . ? C9A C8B C9B 106.3(18) 3_446 . ? O8 C8B C9B 57.0(10) . . ? C8C C8B C9E 111(3) . . ? C9C C8B C9E 23.7(16) . . ? C8A C8B C9E 103(2) 3_446 . ? C9D C8B C9E 109(2) 3_446 . ? C9A C8B C9E 65.3(17) 3_446 . ? O8 C8B C9E 56.1(11) . . ? C9B C8B C9E 102.3(17) . . ? C8C C8B C8D 122(3) . 3_446 ? C9C C8B C8D 38.0(16) . 3_446 ? C8A C8B C8D 64.4(19) 3_446 3_446 ? C9D C8B C8D 79.0(15) 3_446 3_446 ? C9A C8B C8D 26.5(11) 3_446 3_446 ? O8 C8B C8D 86.6(14) . 3_446 ? C9B C8B C8D 106.4(14) . 3_446 ? C9E C8B C8D 38.8(12) . 3_446 ? C9B C8C C8B 147(4) . . ? C9B C8C O8 86(3) . . ? C8B C8C O8 87(3) . . ? C9B C8C C9D 81(3) . 3_446 ? C8B C8C C9D 75(3) . 3_446 ? O8 C8C C9D 122(2) . 3_446 ? C9B C8C C8A 109(3) . 3_446 ? C8B C8C C8A 46(3) . 3_446 ? O8 C8C C8A 114(2) . 3_446 ? C9D C8C C8A 28.8(11) 3_446 3_446 ? C9B C8C C8D 18.9(17) . . ? C8B C8C C8D 133(3) . . ? O8 C8C C8D 69.1(19) . . ? C9D C8C C8D 84(2) 3_446 . ? C8A C8C C8D 107(2) 3_446 . ? C9B C8C C9C 132(3) . . ? C8B C8C C9C 23(2) . . ? O8 C8C C9C 65.0(16) . . ? C9D C8C C9C 83(2) 3_446 . ? C8A C8C C9C 58.1(19) 3_446 . ? C8D C8C C9C 115(2) . . ? C9B C8C C9E 40.3(19) . 3_446 ? C8B C8C C9E 108(3) . 3_446 ? O8 C8C C9E 93(2) . 3_446 ? C9D C8C C9E 45.7(17) 3_446 3_446 ? C8A C8C C9E 70.0(17) 3_446 3_446 ? C8D C8C C9E 38.5(13) . 3_446 ? C9C C8C C9E 101.3(16) . 3_446 ? C9B C8C C9A 44(2) . . ? C8B C8C C9A 113(3) . . ? O8 C8C C9A 45.9(14) . . ? C9D C8C C9A 91(2) 3_446 . ? C8A C8C C9A 105.2(19) 3_446 . ? C8D C8C C9A 25.4(10) . . ? C9C C8C C9A 91.6(16) . . ? C9E C8C C9A 49.8(14) 3_446 . ? C9B C8C C9A 110(3) . 3_446 ? C8B C8C C9A 37(2) . 3_446 ? O8 C8C C9A 90.1(18) . 3_446 ? C9D C8C C9A 44.3(16) 3_446 3_446 ? C8A C8C C9A 24.2(12) 3_446 3_446 ? C8D C8C C9A 100.9(18) . 3_446 ? C9C C8C C9A 38.7(11) . 3_446 ? C9E C8C C9A 70.6(13) 3_446 3_446 ? C9A C8C C9A 89.5(14) . 3_446 ? C8D C9A C8A 150(3) . . ? C8D C9A C9C 75(2) . 3_446 ? C8A C9A C9C 84(2) . 3_446 ? C8D C9A C9D 134(3) . . ? C8A C9A C9D 25(2) . . ? C9C C9A C9D 92.2(17) 3_446 . ? C8D C9A O8 83(2) . . ? C8A C9A O8 92(3) . . ? C9C C9A O8 122.8(17) 3_446 . ? C9D C9A O8 67.4(13) . . ? C8D C9A C8B 108(2) . 3_446 ? C8A C9A C8B 47(2) . 3_446 ? C9C C9A C8B 36.9(12) 3_446 3_446 ? C9D C9A C8B 57.2(17) . 3_446 ? O8 C9A C8B 111.0(18) . 3_446 ? C8D C9A C9B 24.3(17) . . ? C8A C9A C9B 135(3) . . ? C9C C9A C9B 85.0(17) 3_446 . ? C9D C9A C9B 112.5(18) . . ? O8 C9A C9B 59.2(11) . . ? C8B C9A C9B 108.1(16) 3_446 . ? C8D C9A C9E 45.5(17) . 3_446 ? C8A C9A C9E 108(2) . 3_446 ? C9C C9A C9E 31.9(12) 3_446 3_446 ? C9D C9A C9E 104.9(16) . 3_446 ? O8 C9A C9E 100.3(17) . 3_446 ? C8B C9A C9E 62.2(16) 3_446 3_446 ? C9B C9A C9E 53.2(13) . 3_446 ? C8D C9A C8C 46(2) . . ? C8A C9A C8C 116(3) . . ? C9C C9A C8C 92.8(17) 3_446 . ? C9D C9A C8C 92.1(18) . . ? O8 C9A C8C 39.7(12) . . ? C8B C9A C8C 103.8(16) 3_446 . ? C9B C9A C8C 21.7(10) . . ? C9E C9A C8C 63.6(16) 3_446 . ? C8D C9A C8C 110(2) . 3_446 ? C8A C9A C8C 40.8(17) . 3_446 ? C9C C9A C8C 51.4(15) 3_446 3_446 ? C9D C9A C8C 40.9(13) . 3_446 ? O8 C9A C8C 90.8(16) . 3_446 ? C8B C9A C8C 20.5(15) 3_446 3_446 ? C9B C9A C8C 101.2(13) . 3_446 ? C9E C9A C8C 67.8(13) 3_446 3_446 ? C8C C9A C8C 90.5(14) . 3_446 ? C8D C9B C8C 142(3) . . ? C8D C9B C9E 58.0(19) . 3_446 ? C8C C9B C9E 118(2) . 3_446 ? C8D C9B C9D 114(2) . 3_446 ? C8C C9B C9D 65(2) . 3_446 ? C9E C9B C9D 57.9(14) 3_446 3_446 ? C8D C9B O8 84.4(19) . . ? C8C C9B O8 61(2) . . ? C9E C9B O8 110.8(13) 3_446 . ? C9D C9B O8 102.8(12) 3_446 . ? C8D C9B C9A 28.0(18) . . ? C8C C9B C9A 114(3) . . ? C9E C9B C9A 68.3(16) 3_446 . ? C9D C9B C9A 109.3(12) 3_446 . ? O8 C9B C9A 57.4(10) . . ? C8D C9B C8B 130(2) . . ? C8C C9B C8B 17(2) . . ? C9E C9B C8B 102.5(14) 3_446 . ? C9D C9B C8B 53.8(14) 3_446 . ? O8 C9B C8B 58.7(11) . . ? C9A C9B C8B 104.3(14) . . ? C8D C9B C8A 121.5(19) . 3_446 ? C8C C9B C8A 47(2) . 3_446 ? C9E C9B C8A 72.6(13) 3_446 3_446 ? C9D C9B C8A 19.3(10) 3_446 3_446 ? O8 C9B C8A 85.9(11) . 3_446 ? C9A C9B C8A 107.9(11) . 3_446 ? C8B C9B C8A 34.6(11) . 3_446 ? C8D C9B C9C 37.2(15) . 3_446 ? C8C C9B C9C 121(2) . 3_446 ? C9E C9B C9C 26.7(11) 3_446 3_446 ? C9D C9B C9C 76.5(10) 3_446 3_446 ? O8 C9B C9C 89.0(8) . 3_446 ? C9A C9B C9C 41.7(10) . 3_446 ? C8B C9B C9C 104.7(10) . 3_446 ? C8A C9B C9C 85.2(9) 3_446 3_446 ? C8B C9C C9E 133(3) . . ? C8B C9C C9A 83(2) . 3_446 ? C9E C9C C9A 99(2) . 3_446 ? C8B C9C C8D 118(2) . 3_446 ? C9E C9C C8D 62(2) . 3_446 ? C9A C9C C8D 40.3(13) 3_446 3_446 ? C8B C9C C8A 45.6(19) . 3_446 ? C9E C9C C8A 126(2) . 3_446 ? C9A C9C C8A 37.9(13) 3_446 3_446 ? C8D C9C C8A 76.5(14) 3_446 3_446 ? C8B C9C O8 69.3(18) . . ? C9E C9C O8 67.4(17) . . ? C9A C9C O8 115.7(15) 3_446 . ? C8D C9C O8 108.8(15) 3_446 . ? C8A C9C O8 98.5(14) 3_446 . ? C8B C9C C8C 22.0(19) . . ? C9E C9C C8C 111(2) . . ? C9A C9C C8C 89.8(18) 3_446 . ? C8D C9C C8C 115.0(18) 3_446 . ? C8A C9C C8C 56.8(16) 3_446 . ? O8 C9C C8C 48.1(12) . . ? C8B C9C C9B 116(2) . 3_446 ? C9E C9C C9B 46.2(18) . 3_446 ? C9A C9C C9B 53.3(14) 3_446 3_446 ? C8D C9C C9B 20.8(10) 3_446 3_446 ? C8A C9C C9B 83.3(12) 3_446 3_446 ? O8 C9C C9B 88.4(9) . 3_446 ? C8C C9C C9B 104.8(14) . 3_446 ? C8B C9C C9D 39.2(18) . 3_446 ? C9E C9C C9D 115(2) . 3_446 ? C9A C9C C9D 47.0(14) 3_446 3_446 ? C8D C9C C9D 79.3(12) 3_446 3_446 ? C8A C9C C9D 18.3(10) 3_446 3_446 ? O8 C9C C9D 80.6(9) . 3_446 ? C8C C9C C9D 42.9(12) . 3_446 ? C9B C9C C9D 79.4(9) 3_446 3_446 ? C9B C8D C9A 128(3) . . ? C9B C8D C9E 88(2) . 3_446 ? C9A C8D C9E 102(3) . 3_446 ? C9B C8D C9C 122(2) . 3_446 ? C9A C8D C9C 65(2) . 3_446 ? C9E C8D C9C 40.1(13) 3_446 3_446 ? C9B C8D C8C 19.2(17) . . ? C9A C8D C8C 109(3) . . ? C9E C8D C8C 91(2) 3_446 . ? C9C C8D C8C 114.8(17) 3_446 . ? C9B C8D O8 65.9(18) . . ? C9A C8D O8 63(2) . . ? C9E C8D O8 115.4(18) 3_446 . ? C9C C8D O8 107.0(14) 3_446 . ? C8C C8D O8 48.5(13) . . ? C9B C8D C8A 120(2) . . ? C9A C8D C8A 15.1(15) . . ? C9E C8D C8A 89.5(18) 3_446 . ? C9C C8D C8A 55.1(13) 3_446 . ? C8C C8D C8A 101.3(19) . . ? O8 C8D C8A 61.7(12) . . ? C9B C8D C9D 44.0(14) . 3_446 ? C9A C8D C9D 114(2) . 3_446 ? C9E C8D C9D 46.8(17) 3_446 3_446 ? C9C C8D C9D 78.1(12) 3_446 3_446 ? C8C C8D C9D 43.8(14) . 3_446 ? O8 C8D C9D 80.5(12) . 3_446 ? C8A C8D C9D 99.8(11) . 3_446 ? C9B C8D C8B 118(2) . 3_446 ? C9A C8D C8B 45.8(18) . 3_446 ? C9E C8D C8B 56.7(17) 3_446 3_446 ? C9C C8D C8B 23.5(10) 3_446 3_446 ? C8C C8D C8B 104.4(15) . 3_446 ? O8 C8D C8B 84.4(13) . 3_446 ? C8A C8D C8B 33.3(10) . 3_446 ? C9D C8D C8B 80.1(11) 3_446 3_446 ? C8A C9D C8C 86(3) . 3_446 ? C8A C9D C8B 50(2) . 3_446 ? C8C C9D C8B 36.0(17) 3_446 3_446 ? C8A C9D C9E 142(3) . . ? C8C C9D C9E 91(2) 3_446 . ? C8B C9D C9E 116.0(19) 3_446 . ? C8A C9D C9A 33(2) . . ? C8C C9D C9A 95(2) 3_446 . ? C8B C9D C9A 62.7(18) 3_446 . ? C9E C9D C9A 109.5(19) . . ? C8A C9D C9B 118(3) . 3_446 ? C8C C9D C9B 33.5(17) 3_446 3_446 ? C8B C9D C9B 67.8(14) 3_446 3_446 ? C9E C9D C9B 60.5(15) . 3_446 ? C9A C9D C9B 115.5(15) . 3_446 ? C8A C9D O8 89(3) . . ? C8C C9D O8 117.9(18) 3_446 . ? C8B C9D O8 107.1(17) 3_446 . ? C9E C9D O8 58.6(12) . . ? C9A C9D O8 56.9(12) . . ? C9B C9D O8 105.8(13) 3_446 . ? C8A C9D C8D 127(3) . 3_446 ? C8C C9D C8D 52(2) 3_446 3_446 ? C8B C9D C8D 81.2(14) 3_446 3_446 ? C9E C9D C8D 39.4(13) . 3_446 ? C9A C9D C8D 110.4(14) . 3_446 ? C9B C9D C8D 22.4(8) 3_446 3_446 ? O8 C9D C8D 84.8(12) . 3_446 ? C8A C9D C9C 41(2) . 3_446 ? C8C C9D C9C 54.2(19) 3_446 3_446 ? C8B C9D C9C 23.8(12) 3_446 3_446 ? C9E C9D C9C 109.6(14) . 3_446 ? C9A C9D C9C 40.8(11) . 3_446 ? C9B C9D C9C 80.0(11) 3_446 3_446 ? O8 C9D C9C 84.2(10) . 3_446 ? C8D C9D C9C 85.3(10) 3_446 3_446 ? C9C C9E C8D 78(2) . 3_446 ? C9C C9E C9D 132(3) . . ? C8D C9E C9D 94(2) 3_446 . ? C9C C9E C9B 107(2) . 3_446 ? C8D C9E C9B 33.7(12) 3_446 3_446 ? C9D C9E C9B 61.6(15) . 3_446 ? C9C C9E O8 78.5(19) . . ? C8D C9E O8 124(2) 3_446 . ? C9D C9E O8 67.2(13) . . ? C9B C9E O8 113.2(18) 3_446 . ? C9C C9E C8B 23.4(16) . . ? C8D C9E C8B 85(2) 3_446 . ? C9D C9E C8B 110(2) . . ? C9B C9E C8B 104.2(18) 3_446 . ? O8 C9E C8B 57.6(12) . . ? C9C C9E C9A 48.7(17) . 3_446 ? C8D C9E C9A 32.1(14) 3_446 3_446 ? C9D C9E C9A 105(2) . 3_446 ? C9B C9E C9A 58.5(14) 3_446 3_446 ? O8 C9E C9A 99.7(17) . 3_446 ? C8B C9E C9A 52.5(15) . 3_446 ? C9C C9E C8C 111(3) . 3_446 ? C8D C9E C8C 51.0(18) 3_446 3_446 ? C9D C9E C8C 42.9(15) . 3_446 ? C9B C9E C8C 21.4(10) 3_446 3_446 ? O8 C9E C8C 92.9(18) . 3_446 ? C8B C9E C8C 99.6(18) . 3_446 ? C9A C9E C8C 66.6(15) 3_446 3_446 ? C9C C9E C8A 120(3) . . ? C8D C9E C8A 93(2) 3_446 . ? C9D C9E C8A 12.6(11) . . ? C9B C9E C8A 64.2(14) 3_446 . ? O8 C9E C8A 57.3(11) . . ? C8B C9E C8A 97.3(17) . . ? C9A C9E C8A 97.7(17) 3_446 . ? C8C C9E C8A 43.4(13) 3_446 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.92 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.372 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.059 #=END data_Form_F #(1).H2O _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N2 O7 . H2 O' _chemical_formula_sum 'C7 H6 N2 O8' _chemical_formula_weight 246.14 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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.487(4) _cell_length_b 5.8204(16) _cell_length_c 13.462(4) _cell_angle_alpha 90.00 _cell_angle_beta 132.58(2) _cell_angle_gamma 90.00 _cell_volume 951.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description ? _exptl_crystal_colour 'yellow' _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.719 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type none _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '90 minutes' _diffrn_standards_decay_% 5 _diffrn_reflns_number 1952 _diffrn_reflns_av_R_equivalents 0.0058 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 32.46 _reflns_number_total 1867 _reflns_number_gt 1057 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^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 0.00 _refine_ls_number_reflns 1867 _refine_ls_number_parameters 150 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1226 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1296 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.002 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.40177(11) 0.3987(3) 0.27105(19) 0.0338(7) Uani 1 1 d G . . C2 C 0.31206(15) 0.5295(3) 0.16642(19) 0.0323(7) Uani 1 1 d G . . C3 C 0.20589(12) 0.4624(4) 0.10398(18) 0.0335(7) Uani 1 1 d G . . C4 C 0.18943(12) 0.2644(4) 0.14619(19) 0.0353(8) Uani 1 1 d G . . H4 H 0.1184 0.2195 0.1044 0.042 Uiso 1 1 calc . . . C5 C 0.27914(15) 0.1336(3) 0.2508(2) 0.0355(7) Uani 1 1 d G . . C6 C 0.38530(13) 0.2007(3) 0.31326(18) 0.0335(7) Uani 1 1 d G . . H6 H 0.4453 0.1132 0.3833 0.040 Uiso 1 1 calc . . . C7 C 0.5156(2) 0.4754(7) 0.3435(3) 0.0361(7) Uani 1 1 d . . . N2 N 0.1087(2) 0.5838(6) -0.0108(3) 0.0412(7) Uani 1 1 d . . . N1 N 0.2631(2) -0.0662(5) 0.2995(3) 0.0420(7) Uani 1 1 d . . . O7 O 0.32648(18) 0.7195(5) 0.1237(2) 0.0467(7) Uani 1 1 d . . . H7A H 0.3926 0.7428 0.1707 0.070 Uiso 1 1 calc R . . O2 O 0.59174(18) 0.3391(5) 0.4404(2) 0.0503(7) Uani 1 1 d . . . H1A H 0.6524 0.3970 0.4812 0.075 Uiso 1 1 calc R . . O1 O 0.53319(18) 0.6541(5) 0.3128(2) 0.0496(7) Uani 1 1 d . . . O4 O 0.3441(2) -0.1827(5) 0.3868(3) 0.0571(8) Uani 1 1 d . . . O6 O 0.1160(2) 0.7903(5) -0.0164(3) 0.0662(9) Uani 1 1 d . . . O3 O 0.1707(2) -0.1127(6) 0.2514(3) 0.0644(8) Uani 1 1 d . . . O5 O 0.0255(2) 0.4736(6) -0.0952(3) 0.0634(8) Uani 1 1 d . . . O1W O 0.7913(2) 0.4596(6) 0.5890(3) 0.0553(7) Uani 1 1 d D . . H1WA H 0.838(3) 0.367(7) 0.611(5) 0.076(16) Uiso 1 1 d D . . H1WB H 0.820(4) 0.550(7) 0.651(4) 0.088(19) Uiso 1 1 d 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 0.0319(14) 0.0328(19) 0.0368(16) -0.0039(14) 0.0232(13) -0.0011(13) C2 0.0360(15) 0.0293(18) 0.0329(15) -0.0015(13) 0.0238(13) -0.0033(14) C3 0.0309(14) 0.0342(18) 0.0331(15) -0.0022(15) 0.0207(13) 0.0011(15) C4 0.0314(15) 0.036(2) 0.0392(17) -0.0102(15) 0.0241(14) -0.0060(14) C5 0.0370(15) 0.0338(19) 0.0369(16) -0.0031(14) 0.0255(14) -0.0065(14) C6 0.0351(15) 0.0313(17) 0.0308(14) -0.0009(14) 0.0210(13) -0.0007(14) C7 0.0303(14) 0.040(2) 0.0322(15) -0.0026(16) 0.0190(13) -0.0033(16) N2 0.0319(14) 0.0449(19) 0.0381(15) 0.0016(15) 0.0202(13) 0.0043(14) N1 0.0504(16) 0.0321(18) 0.0481(17) -0.0033(14) 0.0351(15) -0.0085(15) O7 0.0369(11) 0.0455(16) 0.0456(13) 0.0138(12) 0.0231(11) 0.0010(11) O2 0.0285(10) 0.0492(17) 0.0521(14) 0.0089(14) 0.0188(10) 0.0001(12) O1 0.0364(11) 0.0531(19) 0.0484(14) 0.0115(14) 0.0243(11) -0.0066(13) O4 0.0602(16) 0.0445(18) 0.0644(17) 0.0147(15) 0.0413(14) 0.0023(15) O6 0.0504(17) 0.0418(17) 0.076(2) 0.0152(16) 0.0303(16) 0.0082(14) O3 0.0544(15) 0.063(2) 0.0774(19) 0.0075(16) 0.0452(15) -0.0130(15) O5 0.0341(11) 0.0615(19) 0.0524(14) -0.0060(16) 0.0124(11) -0.0003(15) O1W 0.0338(12) 0.0508(18) 0.0635(17) -0.0108(16) 0.0258(13) 0.0021(14) _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 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.482(3) . ? C2 O7 1.340(3) . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C3 N2 1.451(3) . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 N1 1.445(3) . ? C6 H6 0.9300 . ? C7 O1 1.224(4) . ? C7 O2 1.300(4) . ? N2 O5 1.214(4) . ? N2 O6 1.215(4) . ? N1 O3 1.216(3) . ? N1 O4 1.225(4) . ? O7 H7A 0.8200 . ? O2 H1A 0.8200 . ? O1W H1WA 0.818(10) . ? O1W H1WB 0.815(10) . ? 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 C6 120.0 . . ? C2 C1 C7 120.49(19) . . ? C6 C1 C7 119.42(19) . . ? O7 C2 C1 120.73(16) . . ? O7 C2 C3 119.27(16) . . ? C1 C2 C3 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 N2 122.59(18) . . ? C4 C3 N2 117.31(18) . . ? C5 C4 C3 120.0 . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 N1 120.32(17) . . ? C6 C5 N1 119.61(17) . . ? C5 C6 C1 120.0 . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O1 C7 O2 124.7(3) . . ? O1 C7 C1 121.1(3) . . ? O2 C7 C1 114.2(3) . . ? O5 N2 O6 124.1(3) . . ? O5 N2 C3 118.3(3) . . ? O6 N2 C3 117.6(3) . . ? O3 N1 O4 123.2(3) . . ? O3 N1 C5 119.0(3) . . ? O4 N1 C5 117.7(3) . . ? C2 O7 H7A 109.5 . . ? C7 O2 H1A 109.5 . . ? H1WA O1W H1WB 108(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 32.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.255 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.054 #=END data_Form_G #(1).C4H10O _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N2 O7 . C4 H10 O' _chemical_formula_sum 'C11 H14 N2 O8' _chemical_formula_weight 302.24 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 Pca21 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 10.290(4) _cell_length_b 5.972(3) _cell_length_c 22.928(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1409.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.123 _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 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 6 _diffrn_reflns_number 3454 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.97 _reflns_number_total 1738 _reflns_number_gt 1082 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0768P)^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 0.00 _refine_ls_number_reflns 1738 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0696(3) 0.5634(4) 0.50117(7) 0.0409(8) Uani 1 1 d G . . C2 C 1.0029(2) 0.4835(4) 0.45273(9) 0.0409(8) Uani 1 1 d G . . C3 C 1.0078(2) 0.6004(4) 0.40035(7) 0.0430(8) Uani 1 1 d G . . C4 C 1.0793(3) 0.7972(4) 0.39641(8) 0.0427(8) Uani 1 1 d G . . H4 H 1.0826 0.8754 0.3614 0.051 Uiso 1 1 calc . . . C5 C 1.1460(2) 0.8772(3) 0.44485(10) 0.0384(8) Uani 1 1 d G . . C6 C 1.1411(2) 0.7603(4) 0.49723(8) 0.0396(8) Uani 1 1 d G . . H6 H 1.1857 0.8138 0.5296 0.048 Uiso 1 1 calc . . . C7 C 1.0684(4) 0.4376(8) 0.55691(18) 0.0540(10) Uani 1 1 d . . . C8 C 1.2828(4) 0.1622(8) 0.69762(18) 0.0547(10) Uani 1 1 d . . . C9 C 1.3312(9) 0.0909(18) 0.6398(3) 0.151(4) Uani 1 1 d . . . H9A H 1.2633 0.0138 0.6192 0.227 Uiso 1 1 calc R . . H9B H 1.4041 -0.0074 0.6447 0.227 Uiso 1 1 calc R . . H9C H 1.3575 0.2201 0.6179 0.227 Uiso 1 1 calc R . . C10 C 1.2563(9) -0.0347(15) 0.7359(4) 0.144(4) Uani 1 1 d . . . H10A H 1.2217 0.0159 0.7724 0.216 Uiso 1 1 calc R . . H10B H 1.3357 -0.1152 0.7426 0.216 Uiso 1 1 calc R . . H10C H 1.1945 -0.1314 0.7172 0.216 Uiso 1 1 calc R . . C11 C 1.3725(8) 0.3123(18) 0.7287(6) 0.175(5) Uani 1 1 d . . . H11A H 1.4049 0.4236 0.7022 0.262 Uiso 1 1 calc R . . H11B H 1.4438 0.2270 0.7440 0.262 Uiso 1 1 calc R . . H11C H 1.3272 0.3843 0.7602 0.262 Uiso 1 1 calc R . . O1 O 1.1359(3) 0.5249(6) 0.59814(13) 0.0678(9) Uani 1 1 d . . . H1A H 1.1316 0.4452 0.6272 0.102 Uiso 1 1 calc R . . O2 O 1.0078(3) 0.2615(6) 0.56099(15) 0.0764(10) Uani 1 1 d . . . O3 O 0.9371(3) 0.2914(5) 0.45613(13) 0.0599(8) Uani 1 1 d . . . H3A H 0.9443 0.2395 0.4891 0.090 Uiso 1 1 calc R . . O4 O 0.8800(5) 0.3612(8) 0.34815(17) 0.1084(16) Uani 1 1 d . . . O5 O 0.9482(4) 0.6538(6) 0.30468(14) 0.0792(10) Uani 1 1 d . . . O6 O 1.2238(4) 1.1778(5) 0.39401(14) 0.0715(10) Uani 1 1 d . . . O7 O 1.2817(4) 1.1407(5) 0.48366(15) 0.0683(9) Uani 1 1 d . . . O8 O 1.1638(3) 0.2843(7) 0.69055(12) 0.0769(11) Uani 1 1 d . . . H8A H 1.1339 0.3153 0.7227 0.115 Uiso 1 1 calc R . . N1 N 0.9406(4) 0.5316(7) 0.34757(16) 0.0591(10) Uani 1 1 d . . . N2 N 1.2215(3) 1.0779(6) 0.44014(15) 0.0488(8) 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 0.0411(19) 0.043(2) 0.0381(18) 0.0050(16) 0.0020(15) -0.0013(17) C2 0.0350(17) 0.043(2) 0.0450(19) -0.0034(17) 0.0027(15) 0.0005(17) C3 0.0401(18) 0.051(2) 0.0378(17) -0.0023(18) -0.0017(16) 0.0070(19) C4 0.0451(19) 0.048(2) 0.0354(17) 0.0074(16) 0.0050(16) 0.0089(18) C5 0.0343(19) 0.0403(18) 0.0404(18) 0.0004(16) 0.0043(15) 0.0029(16) C6 0.0402(18) 0.0415(19) 0.0370(18) 0.0027(15) 0.0014(15) -0.0006(17) C7 0.054(2) 0.057(3) 0.051(2) 0.017(2) 0.006(2) 0.004(2) C8 0.060(2) 0.059(3) 0.046(2) -0.0049(19) -0.002(2) 0.012(2) C9 0.167(8) 0.217(9) 0.070(4) -0.022(5) 0.012(5) 0.107(8) C10 0.136(7) 0.133(7) 0.162(8) 0.058(6) 0.027(6) 0.051(7) C11 0.085(5) 0.175(9) 0.265(12) -0.091(10) -0.035(6) -0.010(6) O1 0.086(2) 0.075(2) 0.0425(14) 0.0158(15) -0.0117(16) -0.0083(19) O2 0.085(2) 0.074(2) 0.071(2) 0.0275(18) -0.002(2) -0.026(2) O3 0.0586(17) 0.0578(18) 0.063(2) 0.0054(15) -0.0036(14) -0.0133(15) O4 0.145(4) 0.111(3) 0.070(2) -0.016(2) -0.029(2) -0.059(3) O5 0.093(2) 0.103(3) 0.0417(16) -0.001(2) -0.0178(17) 0.004(2) O6 0.082(2) 0.069(2) 0.064(2) 0.0258(17) 0.0032(17) -0.0154(19) O7 0.083(2) 0.0566(18) 0.065(2) -0.0036(16) -0.0009(18) -0.0233(18) O8 0.086(2) 0.108(3) 0.0366(15) 0.0209(17) 0.0071(16) 0.035(2) N1 0.054(2) 0.076(3) 0.0469(19) -0.018(2) -0.0066(16) 0.003(2) N2 0.049(2) 0.048(2) 0.0490(18) 0.0031(17) 0.0063(16) -0.0002(17) _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 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.483(4) . ? C2 O3 1.334(3) . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C3 N1 1.453(4) . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 N2 1.433(4) . ? C7 O2 1.226(5) . ? C7 O1 1.284(5) . ? C8 O8 1.434(5) . ? C8 C11 1.471(9) . ? C8 C9 1.479(8) . ? C8 C10 1.492(9) . ? O4 N1 1.194(5) . ? O5 N1 1.227(5) . ? O6 N2 1.214(4) . ? O7 N2 1.233(5) . ? 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 C6 120.0 . . ? C2 C1 C7 120.7(2) . . ? C6 C1 C7 119.3(2) . . ? O3 C2 C1 119.9(2) . . ? O3 C2 C3 120.0(2) . . ? C1 C2 C3 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 N1 115.9(2) . . ? C2 C3 N1 124.1(2) . . ? C5 C4 C3 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 N2 120.3(2) . . ? C4 C5 N2 119.7(2) . . ? C5 C6 C1 120.0 . . ? O2 C7 O1 124.6(4) . . ? O2 C7 C1 120.3(4) . . ? O1 C7 C1 115.1(4) . . ? O8 C8 C11 106.3(5) . . ? O8 C8 C9 109.4(4) . . ? C11 C8 C9 113.5(7) . . ? O8 C8 C10 108.1(5) . . ? C11 C8 C10 108.1(8) . . ? C9 C8 C10 111.2(7) . . ? O4 N1 O5 123.3(4) . . ? O4 N1 C3 118.7(4) . . ? O5 N1 C3 118.0(4) . . ? O6 N2 O7 123.1(4) . . ? O6 N2 C5 119.1(3) . . ? O7 N2 C5 117.8(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.198 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.047 #=END