Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Srinivas Hotha' _publ_contact_author_address ; Division of Organic Chemistry and Center for Materials Charecterization, National Chemical Laboratory Pune-411 008, India ; _publ_contact_author_email S.HOTHA@NCL.RES.IN _publ_section_title ;Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused glycosides and nucleosides by an intramolecular 1,3-dipolar cycloaddition reaction ; loop_ _publ_author_name 'Ramakrishna I. Anegundi' 'Vedavati G. Puranik' 'Srinivas Hotha' # Attachment 'Hotha_2007_4_OBC_Crystal Parameters_Compound 12c.cif' ##Title:Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused ##glycosides and nucleosides by an intramolecular 1,3-dipolar ##cycloaddition reaction ##Communicated to Organic Biomolecular Chemistry ##By Ramakrishna I. Anegundi,Vedavati G. Puranik and Srinivas Hotha ##Division of Organic Chemistry and Center for Materials ##Charecterization, National Chemical Laboratory ##Pune-411 008, India data_compound12c-ria401u _database_code_depnum_ccdc_archive 'CCDC 637450' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Tricyclic compounds' _chemical_melting_point 498 _chemical_formula_moiety 'C14 H15 N5 O6. 0.15H2O' _chemical_formula_sum 'C14 H15.3 N5 O6.15' _chemical_formula_weight 351.98 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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.9329(8) _cell_length_b 14.5318(19) _cell_length_c 18.898(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1629.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 566(2) _cell_measurement_reflns_used 691 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 27.46 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 734 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9770 _exptl_absorpt_correction_T_max 0.9937 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 566(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 ' CCD Area Detector' _diffrn_measurement_device ' Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8097 _diffrn_reflns_av_R_equivalents 0.1045 _diffrn_reflns_av_sigmaI/netI 0.1460 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2861 _reflns_number_gt 1360 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.4528P] 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 riding _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 -4(3) _refine_ls_number_reflns 2861 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1687 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1471 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 0.2166(5) 1.0080(3) 0.08830(17) 0.0505(10) Uani 1 1 d . . . O2 O 0.6779(7) 1.0396(3) 0.1456(2) 0.0799(14) Uani 1 1 d . . . O3 O 0.5085(6) 0.8235(3) 0.0800(2) 0.0695(12) Uani 1 1 d . . . O4 O 0.4322(8) 0.7309(3) 0.1704(3) 0.0805(14) Uani 1 1 d . . . O5 O -0.0493(7) 0.8306(3) 0.2148(2) 0.0730(13) Uani 1 1 d . . . O6 O -0.0757(8) 1.0400(3) 0.3938(2) 0.0870(15) Uani 1 1 d . . . N1 N 0.3401(10) 1.3059(4) 0.1196(3) 0.0736(16) Uani 1 1 d . . . N2 N 0.2770(8) 1.2500(4) 0.0673(3) 0.0657(14) Uani 1 1 d . . . N3 N 0.4329(8) 1.1834(3) 0.0638(2) 0.0528(12) Uani 1 1 d . . . N4 N 0.1687(7) 0.9588(3) 0.2042(2) 0.0518(12) Uani 1 1 d . . . N5 N -0.0505(8) 0.9368(3) 0.3038(2) 0.0595(14) Uani 1 1 d . . . H5 H -0.1376 0.9011 0.3277 0.071 Uiso 1 1 calc R . . C1 C 0.2465(8) 0.9299(4) 0.1337(3) 0.0492(15) Uani 1 1 d . . . H1 H 0.1486 0.8801 0.1170 0.059 Uiso 1 1 calc R . . C2 C 0.4901(8) 0.8993(4) 0.1261(3) 0.0577(17) Uani 1 1 d . . . H2 H 0.5581 0.8861 0.1722 0.069 Uiso 1 1 calc R . . C3 C 0.6047(9) 0.9784(4) 0.0904(3) 0.0641(17) Uani 1 1 d . . . H3 H 0.7314 0.9577 0.0612 0.077 Uiso 1 1 calc R . . C4 C 0.4137(9) 1.0149(4) 0.0455(3) 0.0546(15) Uani 1 1 d . . . H4 H 0.3939 0.9709 0.0067 0.066 Uiso 1 1 calc R . . C5 C 0.4167(10) 1.1087(4) 0.0122(3) 0.0615(17) Uani 1 1 d . . . H5A H 0.5437 1.1126 -0.0199 0.074 Uiso 1 1 calc R . . H5B H 0.2802 1.1167 -0.0153 0.074 Uiso 1 1 calc R . . C6 C 0.5290(12) 1.2718(4) 0.1490(3) 0.0707(19) Uani 1 1 d . . . H6 H 0.6042 1.2973 0.1874 0.085 Uiso 1 1 calc R . . C7 C 0.5938(10) 1.1942(4) 0.1138(3) 0.0586(16) Uani 1 1 d . . . C8 C 0.7749(9) 1.1262(4) 0.1230(4) 0.087(2) Uani 1 1 d . . . H8A H 0.8547 1.1178 0.0787 0.104 Uiso 1 1 calc R . . H8B H 0.8816 1.1479 0.1581 0.104 Uiso 1 1 calc R . . C9 C 0.4787(10) 0.7414(5) 0.1088(4) 0.0691(19) Uani 1 1 d . . . C10 C 0.5096(12) 0.6670(5) 0.0560(4) 0.099(3) Uani 1 1 d . . . H10A H 0.4213 0.6145 0.0695 0.149 Uiso 1 1 calc R . . H10B H 0.6658 0.6500 0.0540 0.149 Uiso 1 1 calc R . . H10C H 0.4615 0.6882 0.0103 0.149 Uiso 1 1 calc R . . C11 C 0.2242(11) 1.0415(5) 0.2319(3) 0.083(2) Uani 1 1 d . . . H11 H 0.3254 1.0777 0.2067 0.100 Uiso 1 1 calc R . . C12 C 0.1437(12) 1.0756(5) 0.2934(3) 0.089(2) Uani 1 1 d . . . H12 H 0.1817 1.1347 0.3079 0.107 Uiso 1 1 calc R . . C13 C -0.0008(11) 1.0195(4) 0.3359(4) 0.0683(19) Uani 1 1 d . . . C14 C 0.0188(9) 0.9020(4) 0.2385(3) 0.0507(15) Uani 1 1 d . . . O7 O 0.965(5) 0.7262(19) 0.0875(16) 0.092(9) Uani 0.15 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 0.044(2) 0.059(3) 0.048(2) 0.009(2) 0.0068(19) 0.0078(18) O2 0.055(3) 0.054(3) 0.130(4) 0.020(3) -0.024(3) -0.001(2) O3 0.095(3) 0.038(2) 0.076(3) 0.012(2) 0.019(2) 0.011(2) O4 0.095(4) 0.060(3) 0.086(3) 0.011(3) -0.002(3) 0.011(2) O5 0.082(3) 0.055(3) 0.082(3) -0.003(3) 0.022(2) -0.019(2) O6 0.116(4) 0.109(4) 0.036(2) 0.002(3) 0.010(3) -0.004(3) N1 0.083(4) 0.069(4) 0.069(4) -0.019(3) 0.015(3) 0.018(3) N2 0.073(4) 0.062(3) 0.062(3) 0.005(3) 0.002(3) 0.024(3) N3 0.056(3) 0.052(3) 0.051(3) 0.006(3) 0.011(3) 0.007(3) N4 0.054(3) 0.057(3) 0.044(3) 0.005(3) -0.003(2) -0.017(2) N5 0.060(3) 0.070(4) 0.048(3) 0.016(3) 0.003(2) -0.015(3) C1 0.058(4) 0.054(4) 0.036(3) 0.008(3) -0.001(3) -0.008(3) C2 0.040(3) 0.056(4) 0.076(4) 0.022(4) 0.006(3) 0.007(3) C3 0.041(3) 0.054(4) 0.098(5) -0.010(4) 0.010(4) 0.001(3) C4 0.066(4) 0.043(4) 0.055(3) 0.015(3) 0.020(3) 0.003(3) C5 0.079(4) 0.062(4) 0.043(3) -0.012(4) 0.018(3) 0.006(4) C6 0.079(5) 0.065(5) 0.068(5) -0.007(4) -0.004(4) -0.001(4) C7 0.042(4) 0.058(4) 0.076(4) 0.004(4) 0.007(4) -0.004(3) C8 0.044(4) 0.061(4) 0.156(7) 0.015(5) -0.010(4) -0.003(3) C9 0.074(5) 0.069(5) 0.064(5) 0.010(5) 0.002(4) 0.007(4) C10 0.131(7) 0.064(5) 0.102(6) -0.014(5) 0.027(5) 0.010(5) C11 0.103(5) 0.095(6) 0.052(4) 0.003(4) 0.007(4) -0.060(4) C12 0.132(6) 0.085(5) 0.050(4) -0.018(4) 0.005(5) -0.049(5) C13 0.083(5) 0.066(5) 0.055(4) 0.004(4) -0.012(4) -0.023(4) C14 0.054(4) 0.047(4) 0.051(4) 0.006(4) 0.001(3) -0.008(3) O7 0.10(2) 0.07(2) 0.11(2) -0.02(2) -0.016(19) -0.013(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 O1 C4 1.425(5) . ? O1 C1 1.434(6) . ? O2 C3 1.438(6) . ? O2 C8 1.448(7) . ? O3 C9 1.323(7) . ? O3 C2 1.408(6) . ? O4 C9 1.206(6) . ? O5 C14 1.201(6) . ? O6 C13 1.218(7) . ? N1 N2 1.332(6) . ? N1 C6 1.345(7) . ? N2 N3 1.341(6) . ? N3 C7 1.353(7) . ? N3 C5 1.461(6) . ? N4 C11 1.352(7) . ? N4 C14 1.375(6) . ? N4 C1 1.471(6) . ? N5 C13 1.378(7) . ? N5 C14 1.396(6) . ? N5 H5 0.8600 . ? C1 C2 1.519(7) . ? C1 H1 0.9800 . ? C2 C3 1.496(7) . ? C2 H2 0.9800 . ? C3 C4 1.512(7) . ? C3 H3 0.9800 . ? C4 C5 1.501(7) . ? C4 H4 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.364(7) . ? C6 H6 0.9300 . ? C7 C8 1.470(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.483(8) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.351(8) . ? C11 H11 0.9300 . ? C12 C13 1.430(8) . ? C12 H12 0.9300 . ? 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 C4 O1 C1 107.1(3) . . ? C3 O2 C8 116.3(5) . . ? C9 O3 C2 116.2(5) . . ? N2 N1 C6 108.4(5) . . ? N1 N2 N3 106.4(4) . . ? N2 N3 C7 111.6(5) . . ? N2 N3 C5 121.6(5) . . ? C7 N3 C5 126.8(5) . . ? C11 N4 C14 120.6(5) . . ? C11 N4 C1 121.9(5) . . ? C14 N4 C1 117.3(5) . . ? C13 N5 C14 129.9(5) . . ? C13 N5 H5 115.0 . . ? C14 N5 H5 115.0 . . ? O1 C1 N4 106.1(4) . . ? O1 C1 C2 107.0(4) . . ? N4 C1 C2 117.9(5) . . ? O1 C1 H1 108.5 . . ? N4 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? O3 C2 C3 106.7(5) . . ? O3 C2 C1 111.2(5) . . ? C3 C2 C1 104.5(5) . . ? O3 C2 H2 111.4 . . ? C3 C2 H2 111.4 . . ? C1 C2 H2 111.4 . . ? O2 C3 C2 106.6(5) . . ? O2 C3 C4 114.6(4) . . ? C2 C3 C4 100.5(4) . . ? O2 C3 H3 111.5 . . ? C2 C3 H3 111.5 . . ? C4 C3 H3 111.5 . . ? O1 C4 C5 108.2(4) . . ? O1 C4 C3 105.7(4) . . ? C5 C4 C3 123.0(5) . . ? O1 C4 H4 106.3 . . ? C5 C4 H4 106.3 . . ? C3 C4 H4 106.3 . . ? N3 C5 C4 113.3(4) . . ? N3 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? N3 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? N1 C6 C7 109.8(6) . . ? N1 C6 H6 125.1 . . ? C7 C6 H6 125.1 . . ? N3 C7 C6 103.7(5) . . ? N3 C7 C8 121.4(6) . . ? C6 C7 C8 134.8(7) . . ? O2 C8 C7 109.2(5) . . ? O2 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? O2 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? O4 C9 O3 122.7(6) . . ? O4 C9 C10 125.8(7) . . ? O3 C9 C10 111.4(6) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 N4 124.9(6) . . ? C12 C11 H11 117.5 . . ? N4 C11 H11 117.5 . . ? C11 C12 C13 119.1(6) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? O6 C13 N5 122.1(6) . . ? O6 C13 C12 125.7(6) . . ? N5 C13 C12 112.2(6) . . ? O5 C14 N4 124.1(5) . . ? O5 C14 N5 122.9(5) . . ? N4 C14 N5 113.0(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 N2 N3 -1.9(6) . . . . ? N1 N2 N3 C7 1.2(6) . . . . ? N1 N2 N3 C5 179.5(4) . . . . ? C4 O1 C1 N4 136.8(4) . . . . ? C4 O1 C1 C2 10.1(5) . . . . ? C11 N4 C1 O1 -43.9(7) . . . . ? C14 N4 C1 O1 130.1(4) . . . . ? C11 N4 C1 C2 76.0(7) . . . . ? C14 N4 C1 C2 -110.1(5) . . . . ? C9 O3 C2 C3 160.9(5) . . . . ? C9 O3 C2 C1 -85.7(6) . . . . ? O1 C1 C2 O3 -99.9(5) . . . . ? N4 C1 C2 O3 140.7(5) . . . . ? O1 C1 C2 C3 14.9(6) . . . . ? N4 C1 C2 C3 -104.5(6) . . . . ? C8 O2 C3 C2 -174.2(4) . . . . ? C8 O2 C3 C4 -64.0(6) . . . . ? O3 C2 C3 O2 -154.2(4) . . . . ? C1 C2 C3 O2 87.9(5) . . . . ? O3 C2 C3 C4 86.0(5) . . . . ? C1 C2 C3 C4 -31.9(6) . . . . ? C1 O1 C4 C5 -164.7(4) . . . . ? C1 O1 C4 C3 -31.3(5) . . . . ? O2 C3 C4 O1 -74.5(5) . . . . ? C2 C3 C4 O1 39.3(5) . . . . ? O2 C3 C4 C5 50.2(7) . . . . ? C2 C3 C4 C5 164.0(5) . . . . ? N2 N3 C5 C4 -122.4(5) . . . . ? C7 N3 C5 C4 55.6(7) . . . . ? O1 C4 C5 N3 63.1(6) . . . . ? C3 C4 C5 N3 -60.5(7) . . . . ? N2 N1 C6 C7 2.0(7) . . . . ? N2 N3 C7 C6 0.0(6) . . . . ? C5 N3 C7 C6 -178.2(5) . . . . ? N2 N3 C7 C8 176.2(5) . . . . ? C5 N3 C7 C8 -1.9(8) . . . . ? N1 C6 C7 N3 -1.2(7) . . . . ? N1 C6 C7 C8 -176.6(7) . . . . ? C3 O2 C8 C7 87.5(7) . . . . ? N3 C7 C8 O2 -64.6(8) . . . . ? C6 C7 C8 O2 110.2(7) . . . . ? C2 O3 C9 O4 2.0(8) . . . . ? C2 O3 C9 C10 -178.1(5) . . . . ? C14 N4 C11 C12 0.4(10) . . . . ? C1 N4 C11 C12 174.2(6) . . . . ? N4 C11 C12 C13 4.0(11) . . . . ? C14 N5 C13 O6 179.9(5) . . . . ? C14 N5 C13 C12 0.2(9) . . . . ? C11 C12 C13 O6 176.2(7) . . . . ? C11 C12 C13 N5 -4.1(9) . . . . ? C11 N4 C14 O5 174.9(6) . . . . ? C1 N4 C14 O5 0.9(8) . . . . ? C11 N4 C14 N5 -4.0(7) . . . . ? C1 N4 C14 N5 -178.0(4) . . . . ? C13 N5 C14 O5 -175.1(6) . . . . ? C13 N5 C14 N4 3.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.189 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.046 data_compound7-ria558n _database_code_depnum_ccdc_archive 'CCDC 637451' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Tetracyclic compounds' _chemical_melting_point 481 _chemical_formula_moiety 'C10 H14 N4 O4' _chemical_formula_sum 'C10 H14 N4 O4' _chemical_formula_weight 254.25 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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.6672(5) _cell_length_b 9.8214(9) _cell_length_c 21.2188(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1181.03(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1985 _cell_measurement_theta_min 2.285 _cell_measurement_theta_max 23.144 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9418 _exptl_absorpt_correction_T_max 0.9926 _exptl_absorpt_process_details 'Bruker SADABS' _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 ' CCD Area Detector' _diffrn_measurement_device ' Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5801 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2080 _reflns_number_gt 1808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.1278P] 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 riding _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 -2.1(16) _refine_ls_number_reflns 2080 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 1.0616(3) 0.84574(14) 0.84345(7) 0.0453(4) Uani 1 1 d . . . O2 O 0.9534(3) 0.63539(16) 0.80267(8) 0.0535(5) Uani 1 1 d . . . O3 O 0.6471(3) 0.63230(14) 0.87143(7) 0.0438(4) Uani 1 1 d . . . O4 O 0.9178(3) 0.86543(14) 0.97743(7) 0.0479(4) Uani 1 1 d . . . N1 N 1.2876(4) 1.1388(2) 0.98418(10) 0.0587(6) Uani 1 1 d . . . N2 N 1.3868(4) 1.1976(2) 0.93202(13) 0.0677(7) Uani 1 1 d . . . N3 N 1.2570(4) 1.1799(2) 0.88263(11) 0.0579(6) Uani 1 1 d . . . N4 N 1.0654(4) 1.10958(16) 0.90241(9) 0.0406(5) Uani 1 1 d . . . C1 C 1.0363(4) 0.7055(2) 0.85659(11) 0.0441(6) Uani 1 1 d . . . H1A H 1.1841 0.6662 0.8722 0.053 Uiso 1 1 calc R . . C2 C 0.8376(4) 0.6919(2) 0.90550(10) 0.0401(6) Uani 1 1 d . . . H2 H 0.8847 0.6372 0.9420 0.048 Uiso 1 1 calc R . . C3 C 0.7755(4) 0.8375(2) 0.92330(10) 0.0398(5) Uani 1 1 d . . . H3 H 0.6069 0.8476 0.9325 0.048 Uiso 1 1 calc R . . C4 C 0.8450(4) 0.9105(2) 0.86200(11) 0.0386(5) Uani 1 1 d . . . H4 H 0.7259 0.8875 0.8302 0.046 Uiso 1 1 calc R . . C5 C 0.8805(4) 1.0638(2) 0.85986(11) 0.0444(6) Uani 1 1 d . . . H5A H 0.9205 1.0906 0.8172 0.053 Uiso 1 1 calc R . . H5B H 0.7336 1.1085 0.8710 0.053 Uiso 1 1 calc R . . C6 C 1.0875(4) 1.0861(2) 0.96422(11) 0.0436(6) Uani 1 1 d . . . C7 C 0.9122(5) 1.0034(2) 0.99973(10) 0.0462(6) Uani 1 1 d . . . H7A H 0.9490 1.0057 1.0444 0.055 Uiso 1 1 calc R . . H7B H 0.7555 1.0411 0.9939 0.055 Uiso 1 1 calc R . . C8 C 0.7452(5) 0.5601(2) 0.81880(10) 0.0438(6) Uani 1 1 d . . . C9 C 0.5744(5) 0.5665(3) 0.76554(12) 0.0684(8) Uani 1 1 d . . . H9A H 0.4295 0.5232 0.7777 0.103 Uiso 1 1 calc R . . H9B H 0.6395 0.5206 0.7296 0.103 Uiso 1 1 calc R . . H9C H 0.5442 0.6600 0.7550 0.103 Uiso 1 1 calc R . . C10 C 0.8114(7) 0.4154(2) 0.83750(14) 0.0775(10) Uani 1 1 d . . . H10A H 0.9125 0.4178 0.8738 0.116 Uiso 1 1 calc R . . H10B H 0.8924 0.3721 0.8032 0.116 Uiso 1 1 calc R . . H10C H 0.6709 0.3651 0.8473 0.116 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 0.0443(10) 0.0336(8) 0.0581(10) -0.0009(7) 0.0089(8) 0.0004(7) O2 0.0515(11) 0.0520(9) 0.0569(10) -0.0159(8) 0.0121(8) -0.0083(9) O3 0.0462(9) 0.0401(8) 0.0451(8) -0.0071(7) 0.0043(7) -0.0069(7) O4 0.0654(11) 0.0364(8) 0.0419(8) -0.0004(6) -0.0116(8) 0.0023(8) N1 0.0458(14) 0.0624(13) 0.0677(14) -0.0182(12) -0.0017(11) 0.0003(11) N2 0.0539(15) 0.0694(15) 0.0797(16) -0.0237(12) 0.0064(14) -0.0135(12) N3 0.0544(14) 0.0475(12) 0.0718(15) -0.0132(10) 0.0106(12) -0.0095(10) N4 0.0402(11) 0.0287(9) 0.0529(12) -0.0039(8) 0.0026(9) -0.0007(8) C1 0.0437(14) 0.0323(11) 0.0562(15) -0.0028(10) -0.0035(12) 0.0058(10) C2 0.0455(14) 0.0305(11) 0.0443(13) 0.0039(9) -0.0038(11) -0.0001(10) C3 0.0436(14) 0.0358(11) 0.0401(12) -0.0007(9) -0.0020(10) 0.0006(11) C4 0.0399(12) 0.0330(10) 0.0429(12) -0.0001(9) -0.0057(10) 0.0023(10) C5 0.0496(15) 0.0342(11) 0.0495(13) 0.0043(10) -0.0041(12) 0.0035(10) C6 0.0424(14) 0.0359(11) 0.0524(14) -0.0120(10) -0.0016(12) 0.0051(11) C7 0.0558(16) 0.0423(12) 0.0407(12) -0.0073(10) -0.0024(12) 0.0009(11) C8 0.0482(14) 0.0379(12) 0.0454(14) -0.0050(10) 0.0058(11) -0.0077(11) C9 0.0645(19) 0.090(2) 0.0511(15) -0.0133(14) -0.0013(14) -0.0063(18) C10 0.115(3) 0.0374(13) 0.080(2) -0.0040(13) 0.0187(19) 0.0070(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.413(2) . ? O1 C4 1.438(3) . ? O2 C1 1.416(3) . ? O2 C8 1.434(3) . ? O3 C2 1.425(3) . ? O3 C8 1.435(3) . ? O4 C3 1.430(3) . ? O4 C7 1.436(2) . ? N1 C6 1.316(3) . ? N1 N2 1.369(3) . ? N2 N3 1.292(3) . ? N3 N4 1.354(3) . ? N4 C6 1.337(3) . ? N4 C5 1.454(3) . ? C1 C2 1.537(3) . ? C1 H1A 0.9800 . ? C2 C3 1.521(3) . ? C2 H2 0.9800 . ? C3 C4 1.536(3) . ? C3 H3 0.9800 . ? C4 C5 1.520(3) . ? C4 H4 0.9800 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.488(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.489(3) . ? C8 C10 1.522(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C4 106.88(17) . . ? C1 O2 C8 109.34(17) . . ? C2 O3 C8 107.72(18) . . ? C3 O4 C7 115.68(16) . . ? C6 N1 N2 105.0(2) . . ? N3 N2 N1 111.4(2) . . ? N2 N3 N4 105.9(2) . . ? C6 N4 N3 108.5(2) . . ? C6 N4 C5 128.5(2) . . ? N3 N4 C5 122.90(19) . . ? O1 C1 O2 110.40(19) . . ? O1 C1 C2 107.02(17) . . ? O2 C1 C2 105.07(18) . . ? O1 C1 H1A 111.4 . . ? O2 C1 H1A 111.4 . . ? C2 C1 H1A 111.4 . . ? O3 C2 C3 109.68(19) . . ? O3 C2 C1 104.38(17) . . ? C3 C2 C1 104.79(17) . . ? O3 C2 H2 112.5 . . ? C3 C2 H2 112.5 . . ? C1 C2 H2 112.5 . . ? O4 C3 C2 104.44(18) . . ? O4 C3 C4 116.48(18) . . ? C2 C3 C4 99.74(17) . . ? O4 C3 H3 111.8 . . ? C2 C3 H3 111.8 . . ? C4 C3 H3 111.8 . . ? O1 C4 C5 108.48(18) . . ? O1 C4 C3 104.15(17) . . ? C5 C4 C3 121.42(19) . . ? O1 C4 H4 107.4 . . ? C5 C4 H4 107.4 . . ? C3 C4 H4 107.4 . . ? N4 C5 C4 112.51(18) . . ? N4 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? N4 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? N1 C6 N4 109.2(2) . . ? N1 C6 C7 128.8(2) . . ? N4 C6 C7 121.9(2) . . ? O4 C7 C6 109.48(18) . . ? O4 C7 H7A 109.8 . . ? C6 C7 H7A 109.8 . . ? O4 C7 H7B 109.8 . . ? C6 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? O2 C8 O3 104.43(16) . . ? O2 C8 C9 109.37(19) . . ? O3 C8 C9 108.5(2) . . ? O2 C8 C10 109.9(2) . . ? O3 C8 C10 110.73(19) . . ? C9 C8 C10 113.4(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 N2 N3 -1.1(3) . . . . ? N1 N2 N3 N4 0.9(3) . . . . ? N2 N3 N4 C6 -0.4(2) . . . . ? N2 N3 N4 C5 -177.12(19) . . . . ? C4 O1 C1 O2 93.3(2) . . . . ? C4 O1 C1 C2 -20.5(2) . . . . ? C8 O2 C1 O1 -125.9(2) . . . . ? C8 O2 C1 C2 -10.8(2) . . . . ? C8 O3 C2 C3 136.03(18) . . . . ? C8 O3 C2 C1 24.2(2) . . . . ? O1 C1 C2 O3 109.19(19) . . . . ? O2 C1 C2 O3 -8.2(2) . . . . ? O1 C1 C2 C3 -6.1(2) . . . . ? O2 C1 C2 C3 -123.49(19) . . . . ? C7 O4 C3 C2 173.25(19) . . . . ? C7 O4 C3 C4 64.4(3) . . . . ? O3 C2 C3 O4 155.48(17) . . . . ? C1 C2 C3 O4 -92.98(19) . . . . ? O3 C2 C3 C4 -83.8(2) . . . . ? C1 C2 C3 C4 27.8(2) . . . . ? C1 O1 C4 C5 169.83(18) . . . . ? C1 O1 C4 C3 39.2(2) . . . . ? O4 C3 C4 O1 70.8(2) . . . . ? C2 C3 C4 O1 -40.8(2) . . . . ? O4 C3 C4 C5 -51.7(3) . . . . ? C2 C3 C4 C5 -163.3(2) . . . . ? C6 N4 C5 C4 -53.9(3) . . . . ? N3 N4 C5 C4 122.2(2) . . . . ? O1 C4 C5 N4 -60.6(2) . . . . ? C3 C4 C5 N4 59.8(3) . . . . ? N2 N1 C6 N4 0.8(2) . . . . ? N2 N1 C6 C7 176.4(2) . . . . ? N3 N4 C6 N1 -0.3(2) . . . . ? C5 N4 C6 N1 176.2(2) . . . . ? N3 N4 C6 C7 -176.27(19) . . . . ? C5 N4 C6 C7 0.2(3) . . . . ? C3 O4 C7 C6 -85.3(2) . . . . ? N1 C6 C7 O4 -109.8(2) . . . . ? N4 C6 C7 O4 65.3(3) . . . . ? C1 O2 C8 O3 25.7(2) . . . . ? C1 O2 C8 C9 141.7(2) . . . . ? C1 O2 C8 C10 -93.2(2) . . . . ? C2 O3 C8 O2 -31.1(2) . . . . ? C2 O3 C8 C9 -147.7(2) . . . . ? C2 O3 C8 C10 87.2(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.144 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.034 data_datam _database_code_depnum_ccdc_archive 'CCDC 666078' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 N3 O4' _chemical_formula_sum 'C11 H15 N3 O4' _chemical_formula_weight 253.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.495(1) _cell_length_b 10.054(2) _cell_length_c 21.330(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1178.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle-like _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.110 _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 'Bruker APEX CCD Area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5138 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.1284 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 23.27 _reflns_number_total 1686 _reflns_number_gt 920 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (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^)+(0.0000P)^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 -2.1(13) _refine_ls_number_reflns 1686 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0357 _refine_ls_wR_factor_gt 0.0306 _refine_ls_goodness_of_fit_ref 0.541 _refine_ls_restrained_S_all 0.541 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0438(6) 0.1828(3) 0.85770(16) 0.0458(9) Uani 1 1 d . . . C2 C 0.1565(6) 0.1731(3) 0.90690(14) 0.0389(9) Uani 1 1 d . . . C3 C 0.2329(6) 0.3164(3) 0.91846(16) 0.0391(8) Uani 1 1 d . . . C4 C 0.1541(6) 0.3806(3) 0.85675(14) 0.0402(8) Uani 1 1 d . . . C5 C 0.1261(7) 0.5290(3) 0.85046(17) 0.0415(9) Uani 1 1 d . . . C6 C 0.1309(7) 0.4929(3) 0.99041(15) 0.0450(10) Uani 1 1 d . . . C7 C -0.0488(7) 0.5767(3) 0.95709(14) 0.0399(9) Uani 1 1 d . . . C8 C -0.2462(7) 0.6496(3) 0.97486(17) 0.0492(10) Uani 1 1 d . . . C13 C 0.4282(9) 0.0292(5) 0.77318(19) 0.0633(12) Uani 1 1 d . . . C14 C 0.2451(7) 0.0327(3) 0.82371(15) 0.0441(9) Uani 1 1 d . . . C15 C 0.1520(10) -0.1032(4) 0.8437(2) 0.0680(12) Uani 1 1 d . . . N16 N -0.0532(5) 0.5855(2) 0.89399(12) 0.0409(7) Uani 1 1 d . . . N17 N -0.2413(5) 0.6587(2) 0.87325(12) 0.0511(8) Uani 1 1 d . . . N18 N -0.3586(5) 0.6994(2) 0.92397(15) 0.0562(8) Uani 1 1 d . . . O9 O -0.0735(4) 0.31862(18) 0.84266(8) 0.0442(6) Uani 1 1 d . . . O10 O 0.0429(4) 0.11229(19) 0.80531(8) 0.0461(6) Uani 1 1 d . . . O11 O 0.3473(4) 0.10268(17) 0.87637(8) 0.0454(6) Uani 1 1 d . . . O12 O 0.1038(4) 0.35618(17) 0.97313(8) 0.0464(6) Uani 1 1 d . . . H1 H -0.195(5) 0.151(2) 0.8700(12) 0.038(10) Uiso 1 1 d . . . H2 H 0.096(4) 0.1301(19) 0.9455(9) 0.018(7) Uiso 1 1 d . . . H3 H 0.397(4) 0.3234(19) 0.9247(9) 0.008(7) Uiso 1 1 d . . . H4 H 0.285(5) 0.349(2) 0.8234(10) 0.053(10) Uiso 1 1 d . . . H8 H -0.288(5) 0.664(2) 1.0194(10) 0.046(9) Uiso 1 1 d . . . H51 H 0.269(5) 0.571(2) 0.8602(11) 0.031(9) Uiso 1 1 d . . . H52 H 0.072(4) 0.559(2) 0.8083(10) 0.036(8) Uiso 1 1 d . . . H61 H 0.100(4) 0.495(2) 1.0371(9) 0.032(8) Uiso 1 1 d . . . H62 H 0.297(5) 0.526(2) 0.9790(11) 0.040(9) Uiso 1 1 d . . . H131 H 0.579(7) -0.010(3) 0.7901(14) 0.114(16) Uiso 1 1 d . . . H132 H 0.363(5) -0.007(2) 0.7396(10) 0.048(10) Uiso 1 1 d . . . H133 H 0.496(6) 0.125(3) 0.7639(13) 0.098(14) Uiso 1 1 d . . . H151 H 0.032(6) -0.102(3) 0.8771(13) 0.101(17) Uiso 1 1 d . . . H152 H 0.280(5) -0.147(3) 0.8539(13) 0.049(13) Uiso 1 1 d . . . H153 H 0.071(6) -0.148(3) 0.8003(13) 0.102(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(3) 0.045(2) 0.057(2) 0.0003(19) -0.003(2) -0.006(2) C2 0.037(2) 0.042(2) 0.037(2) 0.0039(17) 0.0040(18) -0.0014(19) C3 0.030(3) 0.050(2) 0.037(2) -0.0026(18) -0.0020(19) -0.002(2) C4 0.045(2) 0.038(2) 0.038(2) 0.0018(16) 0.002(2) -0.0005(19) C5 0.046(3) 0.042(2) 0.036(2) 0.0021(18) 0.003(2) -0.007(2) C6 0.049(3) 0.051(2) 0.035(2) -0.0066(18) -0.005(2) -0.007(2) C7 0.045(3) 0.045(2) 0.030(2) -0.0040(18) -0.0052(19) -0.005(2) C8 0.051(3) 0.053(2) 0.044(3) -0.009(2) 0.004(2) -0.001(2) C13 0.053(3) 0.095(4) 0.042(3) -0.018(3) -0.003(2) 0.002(3) C14 0.042(2) 0.051(2) 0.039(2) -0.0068(19) -0.0016(18) -0.001(2) C15 0.074(4) 0.048(3) 0.082(4) 0.004(3) -0.014(3) -0.002(3) N16 0.044(2) 0.0353(16) 0.0431(19) -0.0003(14) 0.0012(16) -0.0040(15) N17 0.049(2) 0.0485(18) 0.056(2) -0.0034(15) -0.0068(17) 0.0033(16) N18 0.048(2) 0.0573(19) 0.063(2) -0.0060(17) -0.002(2) 0.0045(17) O9 0.0418(15) 0.0398(13) 0.0510(14) 0.0015(10) -0.0111(12) -0.0016(13) O10 0.0405(15) 0.0507(14) 0.0471(14) -0.0153(12) -0.0121(12) 0.0083(13) O11 0.0400(14) 0.0504(14) 0.0456(13) -0.0089(11) -0.0074(12) 0.0057(12) O12 0.0597(17) 0.0451(14) 0.0344(13) -0.0032(10) 0.0055(12) 0.0018(12) _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 O10 1.406(3) . ? C1 O9 1.412(3) . ? C1 C2 1.524(4) . ? C1 H1 0.93(2) . ? C2 O11 1.423(3) . ? C2 C3 1.520(4) . ? C2 H2 0.988(19) . ? C3 O12 1.423(3) . ? C3 C4 1.529(4) . ? C3 H3 0.91(2) . ? C4 O9 1.429(3) . ? C4 C5 1.505(4) . ? C4 H4 1.06(2) . ? C5 N16 1.468(4) . ? C5 H51 0.92(2) . ? C5 H52 0.995(19) . ? C6 O12 1.431(3) . ? C6 C7 1.480(4) . ? C6 H61 1.011(18) . ? C6 H62 1.00(3) . ? C7 N16 1.349(3) . ? C7 C8 1.363(4) . ? C8 N18 1.345(4) . ? C8 H8 0.99(2) . ? C13 C14 1.475(5) . ? C13 H131 0.99(3) . ? C13 H132 0.88(2) . ? C13 H133 1.05(3) . ? C14 O10 1.424(3) . ? C14 O11 1.439(3) . ? C14 C15 1.520(5) . ? C15 H151 0.97(3) . ? C15 H152 0.86(3) . ? C15 H153 1.12(3) . ? N16 N17 1.344(3) . ? N17 N18 1.324(3) . ? 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 O10 C1 O9 110.2(3) . . ? O10 C1 C2 105.7(3) . . ? O9 C1 C2 107.5(3) . . ? O10 C1 H1 110.9(16) . . ? O9 C1 H1 106.9(16) . . ? C2 C1 H1 115.5(17) . . ? O11 C2 C3 110.0(3) . . ? O11 C2 C1 104.4(2) . . ? C3 C2 C1 104.5(3) . . ? O11 C2 H2 114.4(13) . . ? C3 C2 H2 111.9(12) . . ? C1 C2 H2 110.9(13) . . ? O12 C3 C2 105.2(3) . . ? O12 C3 C4 116.5(3) . . ? C2 C3 C4 100.5(3) . . ? O12 C3 H3 110.5(13) . . ? C2 C3 H3 111.7(13) . . ? C4 C3 H3 111.9(14) . . ? O9 C4 C5 108.9(3) . . ? O9 C4 C3 104.2(2) . . ? C5 C4 C3 121.6(3) . . ? O9 C4 H4 109.0(14) . . ? C5 C4 H4 107.6(13) . . ? C3 C4 H4 105.0(14) . . ? N16 C5 C4 113.3(3) . . ? N16 C5 H51 104.7(16) . . ? C4 C5 H51 110.5(15) . . ? N16 C5 H52 104.7(13) . . ? C4 C5 H52 114.4(13) . . ? H51 C5 H52 109(2) . . ? O12 C6 C7 110.7(3) . . ? O12 C6 H61 104.8(12) . . ? C7 C6 H61 110.6(14) . . ? O12 C6 H62 110.4(14) . . ? C7 C6 H62 107.7(15) . . ? H61 C6 H62 113(2) . . ? N16 C7 C8 103.2(3) . . ? N16 C7 C6 121.9(3) . . ? C8 C7 C6 134.7(3) . . ? N18 C8 C7 109.9(3) . . ? N18 C8 H8 127.7(15) . . ? C7 C8 H8 122.3(15) . . ? C14 C13 H131 108(2) . . ? C14 C13 H132 109(2) . . ? H131 C13 H132 118(3) . . ? C14 C13 H133 110.9(18) . . ? H131 C13 H133 98(3) . . ? H132 C13 H133 112(3) . . ? O10 C14 O11 104.2(2) . . ? O10 C14 C13 110.1(3) . . ? O11 C14 C13 108.4(3) . . ? O10 C14 C15 108.6(3) . . ? O11 C14 C15 110.6(3) . . ? C13 C14 C15 114.4(4) . . ? C14 C15 H151 115(2) . . ? C14 C15 H152 105(2) . . ? H151 C15 H152 112(3) . . ? C14 C15 H153 105.1(15) . . ? H151 C15 H153 110(3) . . ? H152 C15 H153 109(3) . . ? N17 N16 C7 112.2(3) . . ? N17 N16 C5 121.3(3) . . ? C7 N16 C5 126.4(3) . . ? N18 N17 N16 105.9(2) . . ? N17 N18 C8 108.7(3) . . ? C1 O9 C4 105.8(2) . . ? C1 O10 C14 109.2(2) . . ? C2 O11 C14 108.2(2) . . ? C3 O12 C6 115.4(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.099 _refine_diff_density_min -0.091 _refine_diff_density_rms 0.024