# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Alan Kennedy' 'William David' 'Duncan Graham' 'Callum J. McHugh' 'Kenneth Shankland' 'Norman Shankland' 'W. Ewen Smith' _publ_contact_author_name 'Dr Alan Kennedy' _publ_contact_author_address ; Department of Pure and Applied Chemistry University of Strathclyde 295 Cathedral Street Glasgow G1 1XL UNITED KINGDOM ; _publ_contact_author_email A.R.KENNEDY@STRATH.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; The crystal structures of three primary products from the selective reduction of 2,4,6-trinitrotoluene ; data_rtnt _database_code_CSD 220762 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 N3 O4' _chemical_formula_weight 197.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 6.7072(5) _cell_length_b 16.0387(11) _cell_length_c 8.1083(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.160(4) _cell_angle_gamma 90.00 _cell_volume 872.07(10) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3071 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description 'oblong plate' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Kappa Nonius CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7058 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.03 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1515 _reflns_number_gt 1111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo & Collect' _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 w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+0.3782P] 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 1515 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1835 _refine_ls_wR_factor_gt 0.1689 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7523(4) 0.37595(14) 1.0140(3) 0.0787(8) Uani 1 d . . . O2 O 0.7461(4) 0.41961(12) 0.7626(3) 0.0758(7) Uani 1 d . . . O3 O 0.5907(6) 0.1985(3) 0.3353(4) 0.1188(18) Uani 0.798(8) d P . . O4 O 0.8480(6) 0.1215(2) 0.3539(4) 0.0983(16) Uani 0.798(8) d P . . O5 O 0.634(2) 0.1208(10) 0.3553(17) 0.083(5) Uiso 0.202(8) d P . . O6 O 0.896(2) 0.1974(12) 0.337(2) 0.104(6) Uiso 0.202(8) d P . . N1 N 0.7578(5) 0.06932(16) 0.9849(3) 0.0736(9) Uani 1 d . . . H1A H 0.767(5) 0.084(3) 1.092(5) 0.088 Uiso 1 d . . . H1B H 0.753(5) 0.018(3) 0.944(5) 0.088 Uiso 1 d . . . N2 N 0.7481(4) 0.36388(13) 0.8652(3) 0.0561(7) Uani 1 d . . . N3 N 0.7317(5) 0.16452(19) 0.4147(3) 0.0716(8) Uani 1 d . . . C1 C 0.7452(4) 0.11231(15) 0.7007(3) 0.0484(7) Uani 1 d . . . C2 C 0.7526(4) 0.13114(15) 0.8713(3) 0.0488(7) Uani 1 d . . . C3 C 0.7539(4) 0.21434(15) 0.9220(3) 0.0486(7) Uani 1 d . . . H3 H 0.7598 0.2273 1.0338 0.058 Uiso 1 calc R . . C4 C 0.7466(4) 0.27690(15) 0.8068(3) 0.0470(7) Uani 1 d . . . C5 C 0.7361(4) 0.26256(16) 0.6408(3) 0.0527(7) Uani 1 d . . . H5 H 0.7288 0.3057 0.5643 0.063 Uiso 1 calc R . . C6 C 0.7370(4) 0.17935(17) 0.5939(3) 0.0505(7) Uani 1 d . . . C7 C 0.7407(6) 0.02202(17) 0.6494(4) 0.0686(9) Uani 1 d . . . H7A H 0.7247 0.0184 0.5317 0.103 Uiso 1 calc R . . H7B H 0.6311 -0.0055 0.7009 0.103 Uiso 1 calc R . . H7C H 0.8634 -0.0044 0.6830 0.103 Uiso 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 0.131(2) 0.0441(11) 0.0611(15) -0.0138(10) -0.0005(13) 0.0022(11) O2 0.1133(18) 0.0354(10) 0.0789(15) 0.0070(10) 0.0041(13) 0.0003(11) O3 0.127(3) 0.175(5) 0.0533(19) -0.005(2) -0.0210(19) 0.045(3) O4 0.146(4) 0.099(3) 0.0500(17) -0.0150(17) 0.0177(18) 0.042(2) N1 0.136(3) 0.0362(13) 0.0482(15) 0.0041(11) -0.0002(15) 0.0013(14) N2 0.0735(16) 0.0331(12) 0.0617(16) -0.0033(11) 0.0025(11) 0.0004(10) N3 0.105(2) 0.0654(17) 0.0447(15) -0.0012(13) 0.0013(15) -0.0040(18) C1 0.0624(16) 0.0373(13) 0.0455(15) -0.0057(11) 0.0015(12) 0.0028(11) C2 0.0652(16) 0.0372(13) 0.0440(14) 0.0010(11) 0.0015(11) -0.0002(12) C3 0.0663(17) 0.0392(14) 0.0404(13) -0.0019(11) 0.0019(11) 0.0027(11) C4 0.0590(16) 0.0338(13) 0.0483(14) -0.0030(11) 0.0025(11) 0.0008(11) C5 0.0693(18) 0.0418(14) 0.0471(15) 0.0050(12) 0.0015(12) -0.0002(12) C6 0.0670(17) 0.0482(15) 0.0363(14) -0.0041(11) 0.0006(11) -0.0003(12) C7 0.105(2) 0.0401(15) 0.0601(18) -0.0115(13) -0.0002(16) 0.0011(15) _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 N2 1.222(3) . ? O2 N2 1.221(3) . ? O3 N3 1.258(5) . ? O3 O5 1.289(15) . ? O4 N3 1.160(4) . ? O4 O6 1.267(18) . ? O4 O5 1.437(14) . ? O5 N3 1.068(14) . ? O6 N3 1.384(16) . ? N1 C2 1.353(4) . ? N1 H1A 0.90(4) . ? N1 H1B 0.89(4) . ? N2 C4 1.473(3) . ? N3 C6 1.472(4) . ? C1 C6 1.381(4) . ? C1 C2 1.416(4) . ? C1 C7 1.507(4) . ? C2 C3 1.396(4) . ? C3 C4 1.371(4) . ? C3 H3 0.9300 . ? C4 C5 1.366(4) . ? C5 C6 1.388(4) . ? C5 H5 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 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 N3 O3 O5 49.6(7) . . ? N3 O4 O6 69.4(7) . . ? N3 O4 O5 47.1(6) . . ? O6 O4 O5 105.3(10) . . ? N3 O5 O3 63.7(9) . . ? N3 O5 O4 52.7(6) . . ? O3 O5 O4 102.4(10) . . ? O4 O6 N3 51.6(7) . . ? C2 N1 H1A 118(3) . . ? C2 N1 H1B 115(2) . . ? H1A N1 H1B 127(4) . . ? O2 N2 O1 123.8(2) . . ? O2 N2 C4 118.3(2) . . ? O1 N2 C4 117.9(2) . . ? O5 N3 O4 80.2(8) . . ? O5 N3 O3 66.7(8) . . ? O4 N3 O3 123.1(3) . . ? O5 N3 O6 122.2(10) . . ? O4 N3 O6 59.0(7) . . ? O3 N3 O6 101.5(7) . . ? O5 N3 C6 123.6(8) . . ? O4 N3 C6 120.9(3) . . ? O3 N3 C6 116.0(3) . . ? O6 N3 C6 112.5(7) . . ? C6 C1 C2 116.5(2) . . ? C6 C1 C7 125.1(2) . . ? C2 C1 C7 118.3(2) . . ? N1 C2 C3 120.0(2) . . ? N1 C2 C1 120.6(2) . . ? C3 C2 C1 119.4(2) . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 123.3(2) . . ? C5 C4 N2 118.4(2) . . ? C3 C4 N2 118.3(2) . . ? C4 C5 C6 115.6(2) . . ? C4 C5 H5 122.2 . . ? C6 C5 H5 122.2 . . ? C1 C6 C5 125.3(2) . . ? C1 C6 N3 119.5(2) . . ? C5 C6 N3 115.2(2) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 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 N3 O3 O5 O4 -36.8(5) . . . . ? O6 O4 O5 N3 -41.2(10) . . . . ? N3 O4 O5 O3 42.5(6) . . . . ? O6 O4 O5 O3 1.3(12) . . . . ? O5 O4 O6 N3 31.0(7) . . . . ? O3 O5 N3 O4 -132.6(5) . . . . ? O4 O5 N3 O3 132.6(5) . . . . ? O3 O5 N3 O6 -89.2(11) . . . . ? O4 O5 N3 O6 43.4(10) . . . . ? O3 O5 N3 C6 106.7(7) . . . . ? O4 O5 N3 C6 -120.7(6) . . . . ? O6 O4 N3 O5 137.2(11) . . . . ? O6 O4 N3 O3 83.5(9) . . . . ? O5 O4 N3 O3 -53.8(8) . . . . ? O5 O4 N3 O6 -137.2(11) . . . . ? O6 O4 N3 C6 -99.3(8) . . . . ? O5 O4 N3 C6 123.5(8) . . . . ? O5 O3 N3 O4 59.9(9) . . . . ? O5 O3 N3 O6 120.3(11) . . . . ? O5 O3 N3 C6 -117.4(9) . . . . ? O4 O6 N3 O5 -52.2(12) . . . . ? O4 O6 N3 O3 -121.8(5) . . . . ? O4 O6 N3 C6 113.5(5) . . . . ? C6 C1 C2 N1 179.0(3) . . . . ? C7 C1 C2 N1 0.7(4) . . . . ? C6 C1 C2 C3 -0.8(4) . . . . ? C7 C1 C2 C3 -179.1(3) . . . . ? N1 C2 C3 C4 -179.3(3) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C2 C3 C4 N2 180.0(2) . . . . ? O2 N2 C4 C5 -2.2(4) . . . . ? O1 N2 C4 C5 178.1(3) . . . . ? O2 N2 C4 C3 178.4(3) . . . . ? O1 N2 C4 C3 -1.3(4) . . . . ? C3 C4 C5 C6 -1.2(4) . . . . ? N2 C4 C5 C6 179.4(2) . . . . ? C2 C1 C6 C5 0.1(4) . . . . ? C7 C1 C6 C5 178.3(3) . . . . ? C2 C1 C6 N3 179.2(3) . . . . ? C7 C1 C6 N3 -2.6(5) . . . . ? C4 C5 C6 C1 0.8(4) . . . . ? C4 C5 C6 N3 -178.3(3) . . . . ? O5 N3 C6 C1 48.0(11) . . . . ? O4 N3 C6 C1 -51.2(5) . . . . ? O3 N3 C6 C1 126.2(4) . . . . ? O6 N3 C6 C1 -117.5(8) . . . . ? O5 N3 C6 C5 -132.9(10) . . . . ? O4 N3 C6 C5 128.0(4) . . . . ? O3 N3 C6 C5 -54.6(4) . . . . ? O6 N3 C6 C5 61.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.236 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.046 #===END data_g3 _database_code_CSD 220763 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 N3 O4' _chemical_formula_weight 197.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' 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' _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 8.0136(3) _cell_length_b 8.0502(3) _cell_length_c 14.2752(5) _cell_angle_alpha 75.097(2) _cell_angle_beta 74.059(2) _cell_angle_gamma 78.453(2) _cell_volume 847.35(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3612 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'cut block' _exptl_crystal_colour orange-yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13402 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3811 _reflns_number_gt 3221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo & Collect' _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 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+1.0569P] 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 3811 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1852 _refine_ls_wR_factor_gt 0.1794 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1971(3) 0.6132(3) 0.31465(17) 0.0462(5) Uani 1 d . . . O2 O -0.0590(3) 0.6704(3) 0.40947(18) 0.0484(5) Uani 1 d . . . O3 O 0.5285(3) 1.1810(3) 0.40912(17) 0.0481(5) Uani 1 d . . . O4 O 0.6314(3) 1.0134(3) 0.30407(16) 0.0466(5) Uani 1 d . . . O5 O 0.0243(3) -0.0758(2) 0.16801(15) 0.0403(5) Uani 1 d . . . O6 O -0.1619(3) 0.0501(3) 0.07827(15) 0.0386(5) Uani 1 d . . . O7 O 0.4369(2) 0.3445(3) 0.17307(15) 0.0406(5) Uani 1 d . . . O8 O 0.3840(3) 0.5974(3) 0.08002(15) 0.0408(5) Uani 1 d . . . N1 N 0.0885(3) 0.7047(3) 0.36608(17) 0.0346(5) Uani 1 d . . . N2 N -0.1010(3) 1.3030(3) 0.38619(17) 0.0315(5) Uani 1 d . . . H1N H -0.073(4) 1.411(4) 0.378(2) 0.036(8) Uiso 1 d . . . H2N H -0.204(5) 1.287(4) 0.378(2) 0.039(8) Uiso 1 d . . . N3 N 0.5104(3) 1.0800(3) 0.36201(17) 0.0354(5) Uani 1 d . . . N4 N -0.0509(3) 0.0541(3) 0.12166(15) 0.0298(5) Uani 1 d . . . N5 N -0.2672(3) 0.6514(3) 0.13867(18) 0.0337(5) Uani 1 d . . . H3N H -0.360(4) 0.632(4) 0.130(2) 0.034(8) Uiso 1 d . . . H4N H -0.241(5) 0.762(5) 0.134(3) 0.059(11) Uiso 1 d . . . N6 N 0.3449(3) 0.4534(3) 0.12463(15) 0.0297(5) Uani 1 d . . . C1 C 0.3097(3) 0.8755(3) 0.37214(17) 0.0274(5) Uani 1 d . . . C2 C 0.1368(3) 0.8677(3) 0.37294(17) 0.0265(5) Uani 1 d . . . C3 C 0.0010(3) 1.0038(3) 0.37711(17) 0.0260(5) Uani 1 d . . . H3 H -0.1133 0.9866 0.3780 0.031 Uiso 1 calc R . . C4 C 0.0322(3) 1.1671(3) 0.38004(16) 0.0243(5) Uani 1 d . . . C5 C 0.2031(3) 1.1840(3) 0.37820(17) 0.0265(5) Uani 1 d . . . H5 H 0.2301 1.2924 0.3804 0.032 Uiso 1 calc R . . C6 C 0.3328(3) 1.0427(3) 0.37313(17) 0.0273(5) Uani 1 d . . . C7 C 0.4500(4) 0.7196(4) 0.3800(2) 0.0374(6) Uani 1 d . . . H7A H 0.3961 0.6169 0.4199 0.056 Uiso 1 calc R . . H7B H 0.5351 0.7405 0.4121 0.056 Uiso 1 calc R . . H7C H 0.5097 0.7005 0.3131 0.056 Uiso 1 calc R . . C1A C 0.1632(3) 0.2420(3) 0.11835(16) 0.0247(5) Uani 1 d . . . C2A C -0.0084(3) 0.2241(3) 0.12110(16) 0.0248(5) Uani 1 d . . . C3A C -0.1503(3) 0.3546(3) 0.12613(17) 0.0247(5) Uani 1 d . . . H3A H -0.2625 0.3315 0.1270 0.030 Uiso 1 calc R . . C4A C -0.1279(3) 0.5204(3) 0.12988(17) 0.0253(5) Uani 1 d . . . C5A C 0.0404(3) 0.5462(3) 0.12715(17) 0.0249(5) Uani 1 d . . . H5A H 0.0616 0.6575 0.1285 0.030 Uiso 1 calc R . . C6A C 0.1762(3) 0.4106(3) 0.12250(16) 0.0245(5) Uani 1 d . . . C7A C 0.3184(3) 0.1019(3) 0.1020(2) 0.0332(6) Uani 1 d . . . H7D H 0.3350 0.0312 0.1667 0.050 Uiso 1 calc R . . H7E H 0.4239 0.1556 0.0659 0.050 Uiso 1 calc R . . H7F H 0.2968 0.0281 0.0629 0.050 Uiso 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 0.0599(13) 0.0311(10) 0.0546(13) -0.0216(9) -0.0196(10) 0.0024(9) O2 0.0510(13) 0.0367(11) 0.0642(14) -0.0125(10) -0.0130(11) -0.0196(10) O3 0.0386(11) 0.0603(14) 0.0570(13) -0.0216(11) -0.0145(10) -0.0165(10) O4 0.0261(9) 0.0625(14) 0.0480(12) -0.0153(10) -0.0022(8) -0.0031(9) O5 0.0624(13) 0.0227(9) 0.0389(10) -0.0047(8) -0.0196(9) -0.0047(8) O6 0.0406(11) 0.0402(11) 0.0443(11) -0.0170(9) -0.0140(9) -0.0106(8) O7 0.0258(9) 0.0522(12) 0.0417(11) 0.0003(9) -0.0128(8) -0.0073(8) O8 0.0346(10) 0.0379(11) 0.0491(12) -0.0036(9) -0.0057(8) -0.0165(8) N1 0.0476(13) 0.0251(10) 0.0356(12) -0.0055(9) -0.0172(10) -0.0061(9) N2 0.0281(11) 0.0231(10) 0.0443(13) -0.0068(9) -0.0104(9) -0.0035(8) N3 0.0277(11) 0.0440(13) 0.0353(12) -0.0058(10) -0.0095(9) -0.0075(9) N4 0.0365(11) 0.0276(11) 0.0274(10) -0.0098(8) -0.0051(8) -0.0069(9) N5 0.0253(11) 0.0300(11) 0.0465(13) -0.0132(10) -0.0096(9) 0.0028(9) N6 0.0234(10) 0.0360(11) 0.0300(11) -0.0075(9) -0.0043(8) -0.0066(8) C1 0.0294(12) 0.0295(12) 0.0225(11) -0.0073(9) -0.0060(9) -0.0007(9) C2 0.0348(12) 0.0218(11) 0.0248(11) -0.0055(9) -0.0082(9) -0.0061(9) C3 0.0265(11) 0.0270(11) 0.0261(11) -0.0045(9) -0.0072(9) -0.0073(9) C4 0.0277(11) 0.0240(11) 0.0208(10) -0.0033(8) -0.0053(8) -0.0053(9) C5 0.0286(12) 0.0259(11) 0.0260(11) -0.0049(9) -0.0051(9) -0.0090(9) C6 0.0255(11) 0.0341(12) 0.0236(11) -0.0057(9) -0.0057(9) -0.0082(9) C7 0.0373(14) 0.0375(14) 0.0358(14) -0.0118(11) -0.0105(11) 0.0061(11) C1A 0.0249(11) 0.0253(11) 0.0221(11) -0.0047(9) -0.0052(8) -0.0003(9) C2A 0.0297(12) 0.0238(11) 0.0215(10) -0.0057(8) -0.0053(9) -0.0050(9) C3A 0.0218(10) 0.0284(12) 0.0246(11) -0.0069(9) -0.0053(8) -0.0040(9) C4A 0.0251(11) 0.0270(11) 0.0229(11) -0.0069(9) -0.0046(9) -0.0011(9) C5A 0.0266(11) 0.0226(11) 0.0261(11) -0.0060(9) -0.0057(9) -0.0046(9) C6A 0.0214(10) 0.0289(12) 0.0227(11) -0.0037(9) -0.0043(8) -0.0061(9) C7A 0.0300(12) 0.0321(13) 0.0338(13) -0.0082(10) -0.0075(10) 0.0055(10) _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 1.229(3) . ? O2 N1 1.224(3) . ? O3 N3 1.231(3) . ? O4 N3 1.221(3) . ? O5 N4 1.227(3) . ? O6 N4 1.225(3) . ? O7 N6 1.225(3) . ? O8 N6 1.226(3) . ? N1 C2 1.474(3) . ? N2 C4 1.369(3) . ? N2 H1N 0.91(3) . ? N2 H2N 0.90(3) . ? N3 C6 1.471(3) . ? N4 C2A 1.472(3) . ? N5 C4A 1.376(3) . ? N5 H3N 0.84(3) . ? N5 H4N 0.94(4) . ? N6 C6A 1.470(3) . ? C1 C2 1.396(3) . ? C1 C6 1.399(3) . ? C1 C7 1.511(3) . ? C2 C3 1.382(3) . ? C3 C4 1.399(3) . ? C3 H3 0.9500 . ? C4 C5 1.395(3) . ? C5 C6 1.381(3) . ? C5 H5 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C1A C6A 1.400(3) . ? C1A C2A 1.400(3) . ? C1A C7A 1.512(3) . ? C2A C3A 1.385(3) . ? C3A C4A 1.398(3) . ? C3A H3A 0.9500 . ? C4A C5A 1.393(3) . ? C5A C6A 1.380(3) . ? C5A H5A 0.9500 . ? C7A H7D 0.9800 . ? C7A H7E 0.9800 . ? C7A H7F 0.9800 . ? 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 O2 N1 O1 123.7(2) . . ? O2 N1 C2 118.3(2) . . ? O1 N1 C2 118.0(2) . . ? C4 N2 H1N 118(2) . . ? C4 N2 H2N 117(2) . . ? H1N N2 H2N 122(3) . . ? O4 N3 O3 123.5(2) . . ? O4 N3 C6 118.2(2) . . ? O3 N3 C6 118.3(2) . . ? O6 N4 O5 123.6(2) . . ? O6 N4 C2A 118.6(2) . . ? O5 N4 C2A 117.8(2) . . ? C4A N5 H3N 116(2) . . ? C4A N5 H4N 117(2) . . ? H3N N5 H4N 125(3) . . ? O7 N6 O8 123.5(2) . . ? O7 N6 C6A 118.0(2) . . ? O8 N6 C6A 118.4(2) . . ? C2 C1 C6 111.6(2) . . ? C2 C1 C7 124.3(2) . . ? C6 C1 C7 123.9(2) . . ? C3 C2 C1 125.7(2) . . ? C3 C2 N1 114.6(2) . . ? C1 C2 N1 119.8(2) . . ? C2 C3 C4 119.9(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? N2 C4 C5 121.9(2) . . ? N2 C4 C3 120.9(2) . . ? C5 C4 C3 117.2(2) . . ? C6 C5 C4 119.8(2) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 125.8(2) . . ? C5 C6 N3 114.9(2) . . ? C1 C6 N3 119.2(2) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6A C1A C2A 111.7(2) . . ? C6A C1A C7A 124.1(2) . . ? C2A C1A C7A 124.0(2) . . ? C3A C2A C1A 125.6(2) . . ? C3A C2A N4 114.4(2) . . ? C1A C2A N4 120.0(2) . . ? C2A C3A C4A 119.8(2) . . ? C2A C3A H3A 120.1 . . ? C4A C3A H3A 120.1 . . ? N5 C4A C5A 121.4(2) . . ? N5 C4A C3A 121.3(2) . . ? C5A C4A C3A 117.3(2) . . ? C6A C5A C4A 120.1(2) . . ? C6A C5A H5A 119.9 . . ? C4A C5A H5A 119.9 . . ? C5A C6A C1A 125.6(2) . . ? C5A C6A N6 114.6(2) . . ? C1A C6A N6 119.9(2) . . ? C1A C7A H7D 109.5 . . ? C1A C7A H7E 109.5 . . ? H7D C7A H7E 109.5 . . ? C1A C7A H7F 109.5 . . ? H7D C7A H7F 109.5 . . ? H7E C7A H7F 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 C1 C2 C3 -1.8(3) . . . . ? C7 C1 C2 C3 172.3(2) . . . . ? C6 C1 C2 N1 176.4(2) . . . . ? C7 C1 C2 N1 -9.5(4) . . . . ? O2 N1 C2 C3 -34.2(3) . . . . ? O1 N1 C2 C3 143.8(2) . . . . ? O2 N1 C2 C1 147.5(2) . . . . ? O1 N1 C2 C1 -34.6(3) . . . . ? C1 C2 C3 C4 0.6(4) . . . . ? N1 C2 C3 C4 -177.6(2) . . . . ? C2 C3 C4 N2 -178.7(2) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? N2 C4 C5 C6 179.2(2) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 C1 -1.8(4) . . . . ? C4 C5 C6 N3 174.4(2) . . . . ? C2 C1 C6 C5 2.4(3) . . . . ? C7 C1 C6 C5 -171.7(2) . . . . ? C2 C1 C6 N3 -173.7(2) . . . . ? C7 C1 C6 N3 12.1(4) . . . . ? O4 N3 C6 C5 -138.3(2) . . . . ? O3 N3 C6 C5 39.4(3) . . . . ? O4 N3 C6 C1 38.2(3) . . . . ? O3 N3 C6 C1 -144.1(2) . . . . ? C6A C1A C2A C3A 0.7(3) . . . . ? C7A C1A C2A C3A -173.3(2) . . . . ? C6A C1A C2A N4 -177.48(19) . . . . ? C7A C1A C2A N4 8.5(3) . . . . ? O6 N4 C2A C3A 36.1(3) . . . . ? O5 N4 C2A C3A -142.1(2) . . . . ? O6 N4 C2A C1A -145.5(2) . . . . ? O5 N4 C2A C1A 36.3(3) . . . . ? C1A C2A C3A C4A -0.6(4) . . . . ? N4 C2A C3A C4A 177.6(2) . . . . ? C2A C3A C4A N5 -177.5(2) . . . . ? C2A C3A C4A C5A 0.7(3) . . . . ? N5 C4A C5A C6A 177.3(2) . . . . ? C3A C4A C5A C6A -1.0(3) . . . . ? C4A C5A C6A C1A 1.2(4) . . . . ? C4A C5A C6A N6 -177.4(2) . . . . ? C2A C1A C6A C5A -1.0(3) . . . . ? C7A C1A C6A C5A 173.0(2) . . . . ? C2A C1A C6A N6 177.50(19) . . . . ? C7A C1A C6A N6 -8.5(3) . . . . ? O7 N6 C6A C5A 140.4(2) . . . . ? O8 N6 C6A C5A -37.8(3) . . . . ? O7 N6 C6A C1A -38.2(3) . . . . ? O8 N6 C6A C1A 143.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.273 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.064 #===END data_all _database_code_CSD 220764 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 N3 O5' _chemical_formula_weight 213.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.0980(4) _cell_length_b 3.9219(1) _cell_length_c 16.4446(5) _cell_angle_alpha 90.00 _cell_angle_beta 116.586(2) _cell_angle_gamma 90.00 _cell_volume 870.77(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2202 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 27.48 _exptl_crystal_description blade _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10574 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 28.60 _reflns_number_total 2227 _reflns_number_gt 1628 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo & Collect' _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 w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.3098P] 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 2227 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.46018(8) 0.0678(3) 1.18929(7) 0.0350(3) Uani 1 d . . . O2 O 0.42309(8) 0.3829(4) 0.89741(8) 0.0449(3) Uani 1 d . . . O3 O 0.28990(10) 0.2700(4) 0.77678(8) 0.0564(4) Uani 1 d . . . O4 O 0.00181(8) -0.1238(4) 0.90727(9) 0.0501(4) Uani 1 d . . . O5 O 0.03255(9) -0.4536(3) 0.81823(8) 0.0474(4) Uani 1 d . . . N1 N 0.36797(9) -0.1113(4) 1.15370(8) 0.0284(3) Uani 1 d . . . N2 N 0.34052(9) 0.2598(4) 0.85922(8) 0.0298(3) Uani 1 d . . . N3 N 0.05747(9) -0.2492(3) 0.88061(9) 0.0305(3) Uani 1 d . . . C1 C 0.21413(10) -0.1788(4) 1.01962(9) 0.0226(3) Uani 1 d . . . C2 C 0.31330(10) -0.0620(4) 1.05973(9) 0.0228(3) Uani 1 d . . . C3 C 0.35498(10) 0.0799(4) 1.00748(9) 0.0235(3) Uani 1 d . . . H3 H 0.4212 0.1619 1.0350 0.028 Uiso 1 calc R . . C4 C 0.29758(10) 0.0989(4) 0.91418(9) 0.0239(3) Uani 1 d . . . C5 C 0.20108(10) -0.0157(4) 0.87040(9) 0.0252(3) Uani 1 d . . . H5 H 0.1636 -0.0062 0.8062 0.030 Uiso 1 calc R . . C6 C 0.16244(10) -0.1451(4) 0.92603(9) 0.0235(3) Uani 1 d . . . C7 C 0.17170(11) -0.3361(4) 1.07800(10) 0.0302(4) Uani 1 d . . . H7A H 0.1534 -0.1556 1.1089 0.045 Uiso 1 calc R . . H7B H 0.2212 -0.4855 1.1234 0.045 Uiso 1 calc R . . H7C H 0.1128 -0.4696 1.0398 0.045 Uiso 1 calc R . . H1 H 0.4995(18) -0.095(7) 1.2263(16) 0.073(8) Uiso 1 d . . . H2 H 0.3374(13) -0.046(5) 1.1850(12) 0.037(5) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0261(5) 0.0478(7) 0.0235(5) -0.0013(5) 0.0045(4) -0.0021(5) O2 0.0346(6) 0.0658(9) 0.0381(6) 0.0000(6) 0.0197(5) -0.0152(6) O3 0.0587(8) 0.0879(11) 0.0217(6) 0.0009(7) 0.0171(6) -0.0280(8) O4 0.0282(6) 0.0707(10) 0.0554(8) -0.0016(7) 0.0222(6) 0.0012(6) O5 0.0376(7) 0.0412(7) 0.0437(7) -0.0073(6) 0.0007(5) -0.0048(6) N1 0.0245(6) 0.0397(8) 0.0201(6) 0.0003(6) 0.0092(5) 0.0020(6) N2 0.0339(7) 0.0347(8) 0.0249(6) -0.0019(6) 0.0168(5) -0.0026(6) N3 0.0253(6) 0.0311(7) 0.0287(7) 0.0064(6) 0.0063(5) -0.0004(6) C1 0.0247(7) 0.0208(7) 0.0240(7) 0.0011(6) 0.0125(5) 0.0039(6) C2 0.0246(7) 0.0235(7) 0.0193(6) -0.0008(6) 0.0088(5) 0.0057(6) C3 0.0209(6) 0.0255(7) 0.0240(7) -0.0021(6) 0.0100(6) 0.0019(6) C4 0.0278(7) 0.0247(7) 0.0228(7) -0.0002(6) 0.0146(6) 0.0011(6) C5 0.0270(7) 0.0267(8) 0.0190(6) -0.0005(6) 0.0078(6) 0.0021(6) C6 0.0216(7) 0.0220(7) 0.0247(7) -0.0006(6) 0.0085(5) 0.0012(6) C7 0.0315(8) 0.0327(8) 0.0297(8) 0.0053(7) 0.0166(6) 0.0021(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.4299(17) . ? O1 H1 0.90(3) . ? O2 N2 1.2170(17) . ? O3 N2 1.2231(17) . ? O4 N3 1.2124(18) . ? O5 N3 1.2211(18) . ? N1 C2 1.4018(17) . ? N1 H2 0.869(18) . ? N2 C4 1.4697(18) . ? N3 C6 1.4753(18) . ? C1 C6 1.3856(19) . ? C1 C2 1.4151(19) . ? C1 C7 1.5044(19) . ? C2 C3 1.3884(19) . ? C3 C4 1.3859(19) . ? C3 H3 0.9500 . ? C4 C5 1.380(2) . ? C5 C6 1.383(2) . ? C5 H5 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? 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 N1 O1 H1 99.0(16) . . ? C2 N1 O1 111.63(12) . . ? C2 N1 H2 113.9(11) . . ? O1 N1 H2 107.0(12) . . ? O2 N2 O3 123.14(13) . . ? O2 N2 C4 119.01(12) . . ? O3 N2 C4 117.83(12) . . ? O4 N3 O5 124.56(14) . . ? O4 N3 C6 117.78(13) . . ? O5 N3 C6 117.66(13) . . ? C6 C1 C2 116.06(12) . . ? C6 C1 C7 123.98(13) . . ? C2 C1 C7 119.95(12) . . ? C3 C2 N1 122.08(13) . . ? C3 C2 C1 121.29(12) . . ? N1 C2 C1 116.57(12) . . ? C4 C3 C2 118.33(13) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C5 C4 C3 123.45(13) . . ? C5 C4 N2 118.19(12) . . ? C3 C4 N2 118.33(13) . . ? C4 C5 C6 115.72(12) . . ? C4 C5 H5 122.1 . . ? C6 C5 H5 122.1 . . ? C5 C6 C1 125.10(13) . . ? C5 C6 N3 116.24(12) . . ? C1 C6 N3 118.65(12) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 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 O1 N1 C2 C3 13.08(19) . . . . ? O1 N1 C2 C1 -169.74(12) . . . . ? C6 C1 C2 C3 0.5(2) . . . . ? C7 C1 C2 C3 179.09(13) . . . . ? C6 C1 C2 N1 -176.72(13) . . . . ? C7 C1 C2 N1 1.9(2) . . . . ? N1 C2 C3 C4 175.80(14) . . . . ? C1 C2 C3 C4 -1.3(2) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C2 C3 C4 N2 177.91(13) . . . . ? O2 N2 C4 C5 175.05(14) . . . . ? O3 N2 C4 C5 -3.3(2) . . . . ? O2 N2 C4 C3 -2.9(2) . . . . ? O3 N2 C4 C3 178.75(15) . . . . ? C3 C4 C5 C6 1.8(2) . . . . ? N2 C4 C5 C6 -176.06(13) . . . . ? C4 C5 C6 C1 -2.7(2) . . . . ? C4 C5 C6 N3 176.43(13) . . . . ? C2 C1 C6 C5 1.6(2) . . . . ? C7 C1 C6 C5 -176.95(14) . . . . ? C2 C1 C6 N3 -177.51(13) . . . . ? C7 C1 C6 N3 4.0(2) . . . . ? O4 N3 C6 C5 -124.54(16) . . . . ? O5 N3 C6 C5 54.85(18) . . . . ? O4 N3 C6 C1 54.64(19) . . . . ? O5 N3 C6 C1 -125.97(15) . . . . ? _refine_diff_density_max 0.266 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.047 #===END