# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Beatty, Alicia' 'Ugono, Onome' 'Rath, Nigam' _publ_contact_author_name 'Beatty, Alicia' _publ_contact_author_email beattya@umsl.edu _publ_section_title ; Exceptions to the rule: new hydrogen-bonded networks from an old reliable ; # Attachment '- amb1 cec2010 CIF.cif' data_Compound-1 _database_code_depnum_ccdc_archive 'CCDC 793202' #TrackingRef '- amb1 cec2010 CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 N O, C5 H3 N2 O4' _chemical_formula_sum 'C13 H15 N3 O5' _chemical_formula_weight 293.28 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6311(5) _cell_length_b 8.7661(5) _cell_length_c 10.5768(7) _cell_angle_alpha 66.499(3) _cell_angle_beta 79.521(3) _cell_angle_gamma 62.868(2) _cell_volume 653.12(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5234 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 30.53 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9657 _exptl_absorpt_correction_T_max 0.9796 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were located and refined freely. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12194 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 30.55 _reflns_number_total 3789 _reflns_number_gt 3198 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0724P)^2^+0.1593P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3789 _refine_ls_number_parameters 250 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.054 _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 0.79497(11) 0.52045(11) 0.01840(9) 0.01455(18) Uani 1 1 d . . . O2 O 0.65345(10) 0.35219(11) 0.15224(9) 0.01405(18) Uani 1 1 d . . . O3 O 1.43184(11) -0.31606(12) 0.13339(10) 0.0190(2) Uani 1 1 d . . . O4 O 1.22282(12) -0.38822(12) 0.26486(10) 0.0234(2) Uani 1 1 d . . . O5 O 0.69404(11) -0.16839(11) 0.30975(9) 0.01626(19) Uani 1 1 d . . . N1 N 1.09054(12) 0.20825(13) 0.02309(10) 0.0121(2) Uani 1 1 d . . . N2 N 1.22492(12) 0.04312(13) 0.04583(10) 0.0125(2) Uani 1 1 d . . . N3 N 0.48697(13) 0.15646(14) 0.13789(10) 0.0138(2) Uani 1 1 d D . . C1 C 0.78638(14) 0.37059(15) 0.08706(11) 0.0108(2) Uani 1 1 d . . . C2 C 0.94650(14) 0.19928(15) 0.09565(11) 0.0109(2) Uani 1 1 d . . . C3 C 0.98777(14) 0.01580(15) 0.16978(11) 0.0119(2) Uani 1 1 d . . . C4 C 1.16203(14) -0.07542(15) 0.13570(11) 0.0115(2) Uani 1 1 d . . . C5 C 1.27320(15) -0.27613(15) 0.18597(12) 0.0130(2) Uani 1 1 d . . . C6 C 0.41671(15) 0.07215(15) 0.26933(12) 0.0124(2) Uani 1 1 d . . . C7 C 0.52854(14) -0.09934(15) 0.35750(12) 0.0128(2) Uani 1 1 d . . . C8 C 0.46545(16) -0.18276(16) 0.48368(12) 0.0151(2) Uani 1 1 d . . . C9 C 0.29321(16) -0.09376(17) 0.51866(13) 0.0165(2) Uani 1 1 d . . . C10 C 0.18388(16) 0.07691(17) 0.43024(13) 0.0168(2) Uani 1 1 d . . . C11 C 0.24643(15) 0.16230(16) 0.30500(12) 0.0146(2) Uani 1 1 d . . . C12 C 0.81062(16) -0.35214(16) 0.39219(13) 0.0173(2) Uani 1 1 d D . . C13 C 0.76937(19) -0.49495(19) 0.37962(16) 0.0255(3) Uani 1 1 d D . . H1 H 1.107(2) 0.313(2) -0.0285(18) 0.027(4) Uiso 1 1 d . . . H3 H 1.496(3) -0.445(3) 0.158(2) 0.046(6) Uiso 1 1 d . . . H3A H 0.913(2) -0.039(2) 0.2312(17) 0.022(4) Uiso 1 1 d . . . H3B H 0.560(2) 0.204(2) 0.1486(17) 0.026(4) Uiso 1 1 d D . . H3C H 0.552(2) 0.073(2) 0.0942(16) 0.021(4) Uiso 1 1 d D . . H3D H 0.396(2) 0.257(2) 0.0781(16) 0.028(4) Uiso 1 1 d D . . H8 H 0.543(2) -0.305(2) 0.5481(18) 0.026(4) Uiso 1 1 d . . . H9 H 0.249(2) -0.151(2) 0.6053(16) 0.016(4) Uiso 1 1 d . . . H10 H 0.066(2) 0.136(2) 0.4564(18) 0.025(4) Uiso 1 1 d . . . H11 H 0.172(2) 0.285(2) 0.2397(18) 0.025(4) Uiso 1 1 d . . . H12A H 0.9229(19) -0.360(2) 0.3546(17) 0.023(4) Uiso 1 1 d D . . H12B H 0.809(2) -0.366(2) 0.4864(14) 0.015(4) Uiso 1 1 d D . . H13A H 0.646(2) -0.468(3) 0.397(2) 0.036(5) Uiso 1 1 d D . . H13B H 0.798(3) -0.501(3) 0.2881(16) 0.045(6) Uiso 1 1 d D . . H13C H 0.840(3) -0.615(2) 0.446(2) 0.052(6) 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 O1 0.0094(4) 0.0097(4) 0.0202(4) -0.0028(3) 0.0005(3) -0.0029(3) O2 0.0076(4) 0.0112(4) 0.0194(4) -0.0047(3) 0.0029(3) -0.0025(3) O3 0.0103(4) 0.0107(4) 0.0250(5) -0.0040(3) 0.0070(3) 0.0000(3) O4 0.0137(4) 0.0122(4) 0.0324(5) -0.0023(4) 0.0066(4) -0.0030(3) O5 0.0084(4) 0.0130(4) 0.0192(4) -0.0029(3) 0.0022(3) -0.0011(3) N1 0.0079(4) 0.0091(4) 0.0159(5) -0.0036(4) 0.0013(3) -0.0020(4) N2 0.0080(4) 0.0097(4) 0.0158(5) -0.0044(4) 0.0010(3) -0.0011(4) N3 0.0107(5) 0.0122(4) 0.0153(5) -0.0025(4) 0.0009(4) -0.0048(4) C1 0.0072(5) 0.0107(5) 0.0125(5) -0.0042(4) -0.0004(4) -0.0021(4) C2 0.0070(5) 0.0103(5) 0.0137(5) -0.0045(4) 0.0007(4) -0.0023(4) C3 0.0085(5) 0.0107(5) 0.0142(5) -0.0039(4) 0.0016(4) -0.0035(4) C4 0.0089(5) 0.0095(5) 0.0141(5) -0.0044(4) 0.0005(4) -0.0023(4) C5 0.0092(5) 0.0111(5) 0.0145(5) -0.0042(4) 0.0007(4) -0.0016(4) C6 0.0108(5) 0.0120(5) 0.0137(5) -0.0034(4) 0.0010(4) -0.0057(4) C7 0.0088(5) 0.0121(5) 0.0165(5) -0.0051(4) 0.0007(4) -0.0038(4) C8 0.0137(5) 0.0124(5) 0.0165(5) -0.0034(4) 0.0001(4) -0.0051(4) C9 0.0155(6) 0.0169(5) 0.0163(6) -0.0057(4) 0.0036(4) -0.0078(5) C10 0.0108(5) 0.0173(5) 0.0201(6) -0.0078(5) 0.0032(4) -0.0044(4) C11 0.0104(5) 0.0129(5) 0.0183(5) -0.0051(4) -0.0001(4) -0.0036(4) C12 0.0094(5) 0.0123(5) 0.0227(6) -0.0037(5) -0.0012(4) -0.0002(4) C13 0.0222(7) 0.0176(6) 0.0352(8) -0.0133(6) 0.0020(6) -0.0050(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2518(14) . ? O2 C1 1.2689(14) . ? O3 C5 1.3220(14) . ? O3 H3 0.94(2) . ? O4 C5 1.2061(15) . ? O5 C7 1.3618(13) . ? O5 C12 1.4450(14) . ? N1 N2 1.3382(13) . ? N1 C2 1.3546(14) . ? N1 H1 0.924(18) . ? N2 C4 1.3479(15) . ? N3 C6 1.4592(15) . ? N3 H3B 0.941(13) . ? N3 H3C 0.927(13) . ? N3 H3D 0.947(13) . ? C1 C2 1.4891(15) . ? C2 C3 1.3791(15) . ? C3 C4 1.4026(15) . ? C3 H3A 0.975(17) . ? C4 C5 1.4828(15) . ? C6 C11 1.3797(16) . ? C6 C7 1.3954(16) . ? C7 C8 1.3904(16) . ? C8 C9 1.3885(17) . ? C8 H8 0.996(18) . ? C9 C10 1.3859(17) . ? C9 H9 0.957(16) . ? C10 C11 1.3872(17) . ? C10 H10 0.952(18) . ? C11 H11 0.993(17) . ? C12 C13 1.5060(18) . ? C12 H12A 0.962(14) . ? C12 H12B 0.953(13) . ? C13 H13A 0.982(14) . ? C13 H13B 0.971(15) . ? C13 H13C 0.978(15) . ? 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 C5 O3 H3 110.5(12) . . ? C7 O5 C12 116.98(9) . . ? N2 N1 C2 112.97(9) . . ? N2 N1 H1 119.4(11) . . ? C2 N1 H1 127.1(11) . . ? N1 N2 C4 104.13(9) . . ? C6 N3 H3B 112.0(10) . . ? C6 N3 H3C 112.0(10) . . ? H3B N3 H3C 107.3(14) . . ? C6 N3 H3D 110.7(10) . . ? H3B N3 H3D 105.9(14) . . ? H3C N3 H3D 108.6(14) . . ? O1 C1 O2 125.47(10) . . ? O1 C1 C2 117.41(10) . . ? O2 C1 C2 117.11(10) . . ? N1 C2 C3 106.81(9) . . ? N1 C2 C1 120.33(10) . . ? C3 C2 C1 132.84(10) . . ? C2 C3 C4 104.32(10) . . ? C2 C3 H3A 128.2(10) . . ? C4 C3 H3A 127.4(10) . . ? N2 C4 C3 111.76(10) . . ? N2 C4 C5 120.68(10) . . ? C3 C4 C5 127.55(10) . . ? O4 C5 O3 124.64(11) . . ? O4 C5 C4 123.38(11) . . ? O3 C5 C4 111.97(10) . . ? C11 C6 C7 121.81(11) . . ? C11 C6 N3 120.51(10) . . ? C7 C6 N3 117.67(10) . . ? O5 C7 C8 126.02(10) . . ? O5 C7 C6 115.01(10) . . ? C8 C7 C6 118.97(10) . . ? C9 C8 C7 119.30(11) . . ? C9 C8 H8 120.5(10) . . ? C7 C8 H8 120.2(10) . . ? C10 C9 C8 121.07(11) . . ? C10 C9 H9 119.2(9) . . ? C8 C9 H9 119.7(9) . . ? C9 C10 C11 120.01(11) . . ? C9 C10 H10 119.7(11) . . ? C11 C10 H10 120.3(11) . . ? C6 C11 C10 118.82(11) . . ? C6 C11 H11 119.1(10) . . ? C10 C11 H11 122.1(10) . . ? O5 C12 C13 111.53(10) . . ? O5 C12 H12A 102.7(10) . . ? C13 C12 H12A 112.3(10) . . ? O5 C12 H12B 111.5(9) . . ? C13 C12 H12B 110.6(9) . . ? H12A C12 H12B 107.9(13) . . ? C12 C13 H13A 111.2(11) . . ? C12 C13 H13B 110.7(12) . . ? H13A C13 H13B 108.8(16) . . ? C12 C13 H13C 109.1(13) . . ? H13A C13 H13C 109.6(17) . . ? H13B C13 H13C 107.4(18) . . ? 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 C2 N1 N2 C4 0.66(12) . . . . ? N2 N1 C2 C3 -0.86(12) . . . . ? N2 N1 C2 C1 177.71(9) . . . . ? O1 C1 C2 N1 -4.63(15) . . . . ? O2 C1 C2 N1 176.64(9) . . . . ? O1 C1 C2 C3 173.51(11) . . . . ? O2 C1 C2 C3 -5.22(18) . . . . ? N1 C2 C3 C4 0.66(11) . . . . ? C1 C2 C3 C4 -177.66(11) . . . . ? N1 N2 C4 C3 -0.21(12) . . . . ? N1 N2 C4 C5 179.37(10) . . . . ? C2 C3 C4 N2 -0.29(12) . . . . ? C2 C3 C4 C5 -179.83(11) . . . . ? N2 C4 C5 O4 -178.98(11) . . . . ? C3 C4 C5 O4 0.52(19) . . . . ? N2 C4 C5 O3 0.60(15) . . . . ? C3 C4 C5 O3 -179.89(10) . . . . ? C12 O5 C7 C8 5.82(16) . . . . ? C12 O5 C7 C6 -175.02(10) . . . . ? C11 C6 C7 O5 -178.10(10) . . . . ? N3 C6 C7 O5 0.54(15) . . . . ? C11 C6 C7 C8 1.12(17) . . . . ? N3 C6 C7 C8 179.77(10) . . . . ? O5 C7 C8 C9 179.22(10) . . . . ? C6 C7 C8 C9 0.09(17) . . . . ? C7 C8 C9 C10 -0.36(18) . . . . ? C8 C9 C10 C11 -0.56(18) . . . . ? C7 C6 C11 C10 -2.02(17) . . . . ? N3 C6 C11 C10 179.37(10) . . . . ? C9 C10 C11 C6 1.72(18) . . . . ? C7 O5 C12 C13 74.30(13) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.492 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.069 data_Compound-2 _database_code_depnum_ccdc_archive 'CCDC 793203' #TrackingRef '- amb1 cec2010 CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 N, C5 H3 N2 O4, H2 O' _chemical_formula_sum 'C13 H17 N3 O5' _chemical_formula_weight 295.30 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6474(7) _cell_length_b 8.8813(8) _cell_length_c 11.2042(11) _cell_angle_alpha 95.515(5) _cell_angle_beta 105.036(5) _cell_angle_gamma 109.059(4) _cell_volume 680.87(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3453 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 35.60 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9727 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All NH and OH H atoms were located and refined freely. All other H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15758 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 35.69 _reflns_number_total 5646 _reflns_number_gt 4288 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0703P)^2^+0.0510P] 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 5646 _refine_ls_number_parameters 219 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 -0.23524(10) 0.05676(9) 0.80766(7) 0.01289(14) Uani 1 1 d . . . O2 O 0.06616(11) 0.05428(9) 0.85244(8) 0.01558(15) Uani 1 1 d . . . O3 O -0.02029(10) 0.75696(9) 0.82951(7) 0.01281(14) Uani 1 1 d . . . O4 O 0.30266(10) 0.84979(8) 0.91688(7) 0.01244(14) Uani 1 1 d . . . N1 N 0.21351(12) 0.38229(9) 0.95602(8) 0.00973(14) Uani 1 1 d . . . N2 N 0.27181(12) 0.54363(9) 0.96841(8) 0.00987(15) Uani 1 1 d . . . N3 N 0.46830(13) 0.16475(11) 0.83340(8) 0.01237(16) Uani 1 1 d D . . C1 C -0.05516(13) 0.12519(11) 0.84190(9) 0.01006(16) Uani 1 1 d . . . C2 C 0.03302(13) 0.30563(11) 0.87327(9) 0.00944(16) Uani 1 1 d . . . C3 C -0.03145(13) 0.42381(11) 0.82863(9) 0.01019(16) Uani 1 1 d . . . H3 H -0.1531 0.4094 0.7700 0.012 Uiso 1 1 calc R . . C4 C 0.12370(13) 0.56986(11) 0.88972(9) 0.00928(16) Uani 1 1 d . . . C5 C 0.14315(13) 0.73838(11) 0.87990(9) 0.00909(16) Uani 1 1 d . . . C6 C 0.39525(13) 0.20981(12) 0.71319(9) 0.01162(17) Uani 1 1 d . . . C7 C 0.31061(14) 0.09097(12) 0.60286(9) 0.01314(18) Uani 1 1 d . . . C8 C 0.25203(16) 0.14352(14) 0.49102(10) 0.0176(2) Uani 1 1 d . . . H8 H 0.1942 0.0668 0.4136 0.021 Uiso 1 1 calc R . . C9 C 0.27611(18) 0.30503(15) 0.49010(11) 0.0216(2) Uani 1 1 d . . . H9 H 0.2356 0.3375 0.4125 0.026 Uiso 1 1 calc R . . C10 C 0.35878(17) 0.41923(14) 0.60144(11) 0.0201(2) Uani 1 1 d . . . H10 H 0.3739 0.5296 0.6007 0.024 Uiso 1 1 calc R . . C11 C 0.41945(15) 0.37102(13) 0.71423(10) 0.01581(19) Uani 1 1 d . . . H11 H 0.4771 0.4481 0.7914 0.019 Uiso 1 1 calc R . . C12 C 0.28443(17) -0.08402(13) 0.60725(10) 0.0172(2) Uani 1 1 d . . . H12A H 0.1937 -0.1247 0.6560 0.021 Uiso 1 1 calc R . . H12B H 0.4114 -0.0882 0.6536 0.021 Uiso 1 1 calc R . . C13 C 0.20757(18) -0.19830(14) 0.47954(11) 0.0208(2) Uani 1 1 d . . . H13A H 0.0801 -0.1977 0.4332 0.031 Uiso 1 1 calc R . . H13B H 0.1947 -0.3087 0.4919 0.031 Uiso 1 1 calc R . . H13C H 0.2984 -0.1621 0.4313 0.031 Uiso 1 1 calc R . . O1S O 0.40611(11) 0.24757(9) 0.13049(8) 0.01539(15) Uani 1 1 d D . . H1 H 0.284(2) 0.3399(19) 1.0130(15) 0.024(4) Uiso 1 1 d . . . H3N H 0.005(3) 0.881(2) 0.8392(18) 0.047(5) Uiso 1 1 d . . . H3A H 0.564(2) 0.124(2) 0.8307(16) 0.030(4) Uiso 1 1 d D . . H3B H 0.531(2) 0.2565(16) 0.8967(13) 0.022(4) Uiso 1 1 d D . . H3C H 0.377(2) 0.0924(18) 0.8570(16) 0.029(4) Uiso 1 1 d D . . H1SA H 0.334(3) 0.162(2) 0.1502(18) 0.042(5) Uiso 1 1 d D . . H1SB H 0.497(2) 0.220(2) 0.1130(17) 0.039(5) 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 O1 0.0098(3) 0.0098(3) 0.0184(3) 0.0028(3) 0.0034(3) 0.0034(3) O2 0.0120(3) 0.0087(3) 0.0272(4) 0.0035(3) 0.0052(3) 0.0060(3) O3 0.0099(3) 0.0082(3) 0.0198(3) 0.0039(3) 0.0017(3) 0.0045(3) O4 0.0099(3) 0.0085(3) 0.0177(3) 0.0024(2) 0.0026(3) 0.0031(3) N1 0.0098(3) 0.0068(3) 0.0127(3) 0.0026(3) 0.0024(3) 0.0039(3) N2 0.0108(3) 0.0067(3) 0.0125(3) 0.0022(3) 0.0031(3) 0.0041(3) N3 0.0116(3) 0.0122(4) 0.0115(4) 0.0023(3) 0.0020(3) 0.0032(3) C1 0.0114(4) 0.0078(4) 0.0118(4) 0.0032(3) 0.0037(3) 0.0042(3) C2 0.0098(4) 0.0075(4) 0.0119(4) 0.0020(3) 0.0037(3) 0.0040(3) C3 0.0100(4) 0.0086(4) 0.0124(4) 0.0026(3) 0.0027(3) 0.0044(3) C4 0.0097(4) 0.0072(4) 0.0118(4) 0.0026(3) 0.0034(3) 0.0039(3) C5 0.0101(4) 0.0080(4) 0.0104(4) 0.0019(3) 0.0036(3) 0.0046(3) C6 0.0095(4) 0.0135(4) 0.0117(4) 0.0034(3) 0.0023(3) 0.0045(3) C7 0.0116(4) 0.0144(4) 0.0122(4) 0.0017(3) 0.0024(3) 0.0044(4) C8 0.0180(5) 0.0194(5) 0.0125(4) 0.0028(4) 0.0019(4) 0.0053(4) C9 0.0228(5) 0.0225(5) 0.0176(5) 0.0092(4) 0.0022(4) 0.0076(5) C10 0.0206(5) 0.0166(5) 0.0223(5) 0.0079(4) 0.0029(4) 0.0076(4) C11 0.0153(4) 0.0136(4) 0.0173(4) 0.0029(4) 0.0033(4) 0.0051(4) C12 0.0203(5) 0.0143(4) 0.0136(4) 0.0005(4) 0.0015(4) 0.0055(4) C13 0.0227(5) 0.0182(5) 0.0172(5) -0.0023(4) 0.0025(4) 0.0067(4) O1S 0.0121(3) 0.0133(3) 0.0242(4) 0.0086(3) 0.0071(3) 0.0065(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 O1 C1 1.2440(12) . ? O2 C1 1.2690(11) . ? O3 C5 1.3017(11) . ? O3 H3N 1.04(2) . ? O4 C5 1.2286(11) . ? N1 N2 1.3356(11) . ? N1 C2 1.3525(12) . ? N1 H1 0.916(16) . ? N2 C4 1.3446(12) . ? N3 C6 1.4648(13) . ? N3 H3A 0.926(13) . ? N3 H3B 0.925(12) . ? N3 H3C 0.900(13) . ? C1 C2 1.4864(13) . ? C2 C3 1.3805(13) . ? C3 C4 1.4006(13) . ? C3 H3 0.9500 . ? C4 C5 1.4728(13) . ? C6 C11 1.3809(15) . ? C6 C7 1.3960(14) . ? C7 C8 1.3952(15) . ? C7 C12 1.5081(15) . ? C8 C9 1.3867(16) . ? C8 H8 0.9500 . ? C9 C10 1.3832(17) . ? C9 H9 0.9500 . ? C10 C11 1.3875(15) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.5226(15) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O1S H1SA 0.865(15) . ? O1S H1SB 0.868(15) . ? 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 C5 O3 H3N 108.9(11) . . ? N2 N1 C2 112.15(8) . . ? N2 N1 H1 118.5(10) . . ? C2 N1 H1 128.0(10) . . ? N1 N2 C4 104.96(8) . . ? C6 N3 H3A 110.3(11) . . ? C6 N3 H3B 110.0(10) . . ? H3A N3 H3B 104.2(14) . . ? C6 N3 H3C 114.5(11) . . ? H3A N3 H3C 108.7(15) . . ? H3B N3 H3C 108.6(14) . . ? O1 C1 O2 125.70(9) . . ? O1 C1 C2 119.50(8) . . ? O2 C1 C2 114.80(8) . . ? N1 C2 C3 107.33(8) . . ? N1 C2 C1 120.54(8) . . ? C3 C2 C1 132.06(9) . . ? C2 C3 C4 104.10(8) . . ? C2 C3 H3 127.9 . . ? C4 C3 H3 127.9 . . ? N2 C4 C3 111.45(8) . . ? N2 C4 C5 118.68(8) . . ? C3 C4 C5 129.87(8) . . ? O4 C5 O3 124.12(9) . . ? O4 C5 C4 121.38(8) . . ? O3 C5 C4 114.50(8) . . ? C11 C6 C7 122.88(9) . . ? C11 C6 N3 117.76(9) . . ? C7 C6 N3 119.33(9) . . ? C8 C7 C6 116.36(10) . . ? C8 C7 C12 122.90(9) . . ? C6 C7 C12 120.74(9) . . ? C9 C8 C7 121.59(10) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C10 C9 C8 120.46(10) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.36(10) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C6 C11 C10 119.34(10) . . ? C6 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C7 C12 C13 115.38(9) . . ? C7 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? C7 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? H1SA O1S H1SB 104.4(16) . . ? 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 C2 N1 N2 C4 -0.63(11) . . . . ? N2 N1 C2 C3 -0.09(11) . . . . ? N2 N1 C2 C1 177.33(8) . . . . ? O1 C1 C2 N1 152.76(9) . . . . ? O2 C1 C2 N1 -27.75(13) . . . . ? O1 C1 C2 C3 -30.57(16) . . . . ? O2 C1 C2 C3 148.93(11) . . . . ? N1 C2 C3 C4 0.74(10) . . . . ? C1 C2 C3 C4 -176.27(10) . . . . ? N1 N2 C4 C3 1.12(11) . . . . ? N1 N2 C4 C5 -179.32(8) . . . . ? C2 C3 C4 N2 -1.18(11) . . . . ? C2 C3 C4 C5 179.33(9) . . . . ? N2 C4 C5 O4 17.38(14) . . . . ? C3 C4 C5 O4 -163.15(10) . . . . ? N2 C4 C5 O3 -162.73(9) . . . . ? C3 C4 C5 O3 16.74(14) . . . . ? C11 C6 C7 C8 0.66(15) . . . . ? N3 C6 C7 C8 -177.23(9) . . . . ? C11 C6 C7 C12 -178.92(10) . . . . ? N3 C6 C7 C12 3.19(14) . . . . ? C6 C7 C8 C9 -0.28(16) . . . . ? C12 C7 C8 C9 179.29(11) . . . . ? C7 C8 C9 C10 -0.38(18) . . . . ? C8 C9 C10 C11 0.67(18) . . . . ? C7 C6 C11 C10 -0.38(16) . . . . ? N3 C6 C11 C10 177.55(10) . . . . ? C9 C10 C11 C6 -0.31(17) . . . . ? C8 C7 C12 C13 5.83(15) . . . . ? C6 C7 C12 C13 -174.62(10) . . . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.562 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.068 data_Compound-3 _database_code_depnum_ccdc_archive 'CCDC 793204' #TrackingRef '- amb1 cec2010 CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 N, C5 H3 N2 O4, H2 O' _chemical_formula_sum 'C15 H21 N3 O5' _chemical_formula_weight 323.35 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8953(2) _cell_length_b 9.5137(5) _cell_length_c 10.4456(3) _cell_angle_alpha 106.7590(10) _cell_angle_beta 108.9500(10) _cell_angle_gamma 99.0420(10) _cell_volume 769.25(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5823 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 33.90 _exptl_crystal_description prism _exptl_crystal_colour 'light pink' _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9431 _exptl_absorpt_correction_T_max 0.9539 _exptl_absorpt_process_details 'SADABS, G. Sheldrick (1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART APEX II' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19930 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 33.90 _reflns_number_total 5823 _reflns_number_gt 5435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II' _computing_cell_refinement 'APEX II' _computing_data_reduction 'APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED, L.Barbour (1999); http://x-seed.net/' _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^)+(0.0559P)^2^+0.1963P] 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 5823 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.72273(6) 0.46644(5) 0.14449(6) 0.01304(10) Uani 1 1 d . . . N1 N 0.70096(7) 0.79620(6) 0.26131(6) 0.01184(10) Uani 1 1 d . . . C1 C 0.75701(8) 0.89795(7) 0.41377(7) 0.01139(11) Uani 1 1 d . . . O2 O 0.65733(6) 0.21085(6) 0.07449(6) 0.01442(10) Uani 1 1 d . . . N2 N 0.97172(7) 0.21838(6) 0.07414(6) 0.01103(10) Uani 1 1 d . . . C2 C 0.69190(8) 1.02328(7) 0.44154(7) 0.01195(11) Uani 1 1 d . . . O3 O 1.39634(6) 0.64215(6) 0.20200(6) 0.01558(10) Uani 1 1 d . . . N3 N 1.12650(7) 0.26773(6) 0.08578(6) 0.01094(10) Uani 1 1 d . . . C3 C 0.73881(9) 1.11572(8) 0.58661(7) 0.01567(12) Uani 1 1 d . . . H3 H 0.6961 1.2009 0.6094 0.019 Uiso 1 1 calc R . . O4 O 1.43047(6) 0.40952(6) 0.11196(7) 0.01882(11) Uani 1 1 d . . . C4 C 0.84744(10) 1.08464(9) 0.69837(8) 0.01831(13) Uani 1 1 d . . . H4 H 0.8786 1.1490 0.7965 0.022 Uiso 1 1 calc R . . O1S O 0.69576(6) 0.91584(6) 0.03266(6) 0.01280(9) Uani 1 1 d . . . C5 C 0.91025(9) 0.96046(9) 0.66717(8) 0.01722(13) Uani 1 1 d . . . H5 H 0.9850 0.9410 0.7443 0.021 Uiso 1 1 calc R . . C6 C 0.86496(8) 0.86312(8) 0.52338(7) 0.01368(11) Uani 1 1 d . . . C7 C 0.57478(9) 1.05548(8) 0.31848(7) 0.01475(12) Uani 1 1 d . . . H7A H 0.4788 0.9640 0.2599 0.018 Uiso 1 1 calc R . . H7B H 0.6321 1.0719 0.2549 0.018 Uiso 1 1 calc R . . C8 C 0.51099(10) 1.19312(9) 0.36578(8) 0.01843(13) Uani 1 1 d . . . H8A H 0.4516 1.1774 0.4270 0.028 Uiso 1 1 calc R . . H8B H 0.4358 1.2052 0.2798 0.028 Uiso 1 1 calc R . . H8C H 0.6045 1.2853 0.4209 0.028 Uiso 1 1 calc R . . C9 C 0.92468(9) 0.72177(8) 0.49594(8) 0.01700(13) Uani 1 1 d . . . H9A H 1.0341 0.7421 0.5735 0.020 Uiso 1 1 calc R . . H9B H 0.9379 0.6962 0.4021 0.020 Uiso 1 1 calc R . . C10 C 0.80292(10) 0.58610(9) 0.49227(9) 0.02039(14) Uani 1 1 d . . . H10A H 0.7912 0.6107 0.5857 0.031 Uiso 1 1 calc R . . H10B H 0.8447 0.4960 0.4743 0.031 Uiso 1 1 calc R . . H10C H 0.6950 0.5648 0.4144 0.031 Uiso 1 1 calc R . . C11 C 0.92669(7) 0.34709(7) 0.11703(7) 0.00970(10) Uani 1 1 d . . . C12 C 1.05443(7) 0.47862(7) 0.15667(7) 0.01073(11) Uani 1 1 d . . . H12 H 1.0534 0.5823 0.1910 0.013 Uiso 1 1 calc R . . C13 C 1.18168(7) 0.42271(7) 0.13441(7) 0.01009(10) Uani 1 1 d . . . C14 C 1.34957(8) 0.49944(7) 0.15156(7) 0.01128(11) Uani 1 1 d . . . C15 C 0.75673(7) 0.33510(7) 0.11041(7) 0.01028(11) Uani 1 1 d . . . H1 H 0.7069(16) 0.8490(15) 0.2028(14) 0.024(3) Uiso 1 1 d . . . H2 H 1.1791(18) 0.1968(16) 0.0580(15) 0.029(3) Uiso 1 1 d . . . H7 H 0.7612(16) 0.7312(15) 0.2519(14) 0.025(3) Uiso 1 1 d . . . H8 H 0.5935(19) 0.8686(17) -0.0143(16) 0.032(3) Uiso 1 1 d . . . H9 H 0.7031(18) 1.0073(18) 0.0432(16) 0.033(3) Uiso 1 1 d . . . H6 H 0.5875(17) 0.7360(16) 0.2286(15) 0.027(3) Uiso 1 1 d . . . H10 H 0.602(3) 0.448(2) 0.134(2) 0.063(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.00921(19) 0.0099(2) 0.0197(2) 0.00306(17) 0.00721(17) 0.00286(15) N1 0.0114(2) 0.0109(2) 0.0125(2) 0.00320(18) 0.00502(18) 0.00231(18) C1 0.0103(2) 0.0109(2) 0.0112(2) 0.00330(19) 0.00385(19) 0.00052(19) O2 0.0099(2) 0.0105(2) 0.0237(2) 0.00575(17) 0.00829(17) 0.00213(16) N2 0.0078(2) 0.0114(2) 0.0148(2) 0.00453(18) 0.00549(18) 0.00299(17) C2 0.0124(3) 0.0106(2) 0.0121(2) 0.0037(2) 0.0053(2) 0.0013(2) O3 0.0120(2) 0.0113(2) 0.0210(2) 0.00179(18) 0.00828(18) 0.00073(16) N3 0.0078(2) 0.0106(2) 0.0154(2) 0.00447(18) 0.00567(18) 0.00317(17) C3 0.0187(3) 0.0127(3) 0.0131(3) 0.0026(2) 0.0064(2) 0.0013(2) O4 0.0104(2) 0.0134(2) 0.0355(3) 0.0075(2) 0.0128(2) 0.00527(17) C4 0.0204(3) 0.0170(3) 0.0117(3) 0.0029(2) 0.0038(2) -0.0007(2) O1S 0.0108(2) 0.0105(2) 0.0161(2) 0.00353(16) 0.00529(17) 0.00297(16) C5 0.0147(3) 0.0190(3) 0.0138(3) 0.0070(2) 0.0019(2) -0.0003(2) C6 0.0102(2) 0.0147(3) 0.0153(3) 0.0070(2) 0.0038(2) 0.0009(2) C7 0.0179(3) 0.0148(3) 0.0137(3) 0.0058(2) 0.0071(2) 0.0069(2) C8 0.0221(3) 0.0158(3) 0.0215(3) 0.0081(2) 0.0109(3) 0.0088(2) C9 0.0124(3) 0.0187(3) 0.0216(3) 0.0105(3) 0.0055(2) 0.0051(2) C10 0.0206(3) 0.0176(3) 0.0254(3) 0.0116(3) 0.0090(3) 0.0046(3) C11 0.0070(2) 0.0106(2) 0.0118(2) 0.00381(19) 0.00432(19) 0.00256(18) C12 0.0082(2) 0.0103(2) 0.0137(2) 0.0035(2) 0.00511(19) 0.00253(19) C13 0.0072(2) 0.0103(2) 0.0128(2) 0.00381(19) 0.00446(19) 0.00207(18) C14 0.0075(2) 0.0123(3) 0.0145(3) 0.0047(2) 0.00503(19) 0.00256(19) C15 0.0082(2) 0.0112(2) 0.0119(2) 0.00398(19) 0.00475(19) 0.00279(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 C15 1.3083(8) . ? O1 H10 1.03(2) . ? N1 C1 1.4716(8) . ? N1 H1 0.904(13) . ? N1 H7 0.884(13) . ? N1 H6 0.972(14) . ? C1 C6 1.3955(9) . ? C1 C2 1.4029(9) . ? O2 C15 1.2329(8) . ? N2 N3 1.3365(7) . ? N2 C11 1.3472(8) . ? C2 C3 1.3961(9) . ? C2 C7 1.5131(9) . ? O3 C14 1.2497(8) . ? N3 C13 1.3607(8) . ? N3 H2 0.913(14) . ? C3 C4 1.3930(10) . ? C3 H3 0.9500 . ? O4 C14 1.2663(8) . ? C4 C5 1.3848(11) . ? C4 H4 0.9500 . ? O1S H8 0.851(15) . ? O1S H9 0.834(15) . ? C5 C6 1.4012(10) . ? C5 H5 0.9500 . ? C6 C9 1.5079(10) . ? C7 C8 1.5242(10) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5315(11) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.4061(8) . ? C11 C15 1.4754(8) . ? C12 C13 1.3811(8) . ? C12 H12 0.9500 . ? C13 C14 1.4844(9) . ? 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 C15 O1 H10 109.2(11) . . ? C1 N1 H1 111.9(8) . . ? C1 N1 H7 111.2(8) . . ? H1 N1 H7 107.9(12) . . ? C1 N1 H6 109.1(8) . . ? H1 N1 H6 109.5(11) . . ? H7 N1 H6 107.1(11) . . ? C6 C1 C2 123.14(6) . . ? C6 C1 N1 119.52(6) . . ? C2 C1 N1 117.28(6) . . ? N3 N2 C11 104.33(5) . . ? C3 C2 C1 117.34(6) . . ? C3 C2 C7 121.71(6) . . ? C1 C2 C7 120.95(6) . . ? N2 N3 C13 112.90(5) . . ? N2 N3 H2 118.3(9) . . ? C13 N3 H2 128.8(9) . . ? C4 C3 C2 120.86(7) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 120.34(7) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? H8 O1S H9 106.0(14) . . ? C4 C5 C6 120.89(6) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 117.42(6) . . ? C1 C6 C9 123.66(6) . . ? C5 C6 C9 118.76(6) . . ? C2 C7 C8 114.89(6) . . ? C2 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? C2 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 C10 111.18(6) . . ? C6 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C6 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? 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 . . ? N2 C11 C12 111.80(5) . . ? N2 C11 C15 119.17(5) . . ? C12 C11 C15 128.95(6) . . ? C13 C12 C11 104.24(5) . . ? C13 C12 H12 127.9 . . ? C11 C12 H12 127.9 . . ? N3 C13 C12 106.73(5) . . ? N3 C13 C14 120.99(5) . . ? C12 C13 C14 132.27(6) . . ? O3 C14 O4 127.03(6) . . ? O3 C14 C13 118.31(6) . . ? O4 C14 C13 114.66(6) . . ? O2 C15 O1 124.08(6) . . ? O2 C15 C11 121.89(6) . . ? O1 C15 C11 114.03(5) . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.558 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.052 data_Compound-4 _database_code_depnum_ccdc_archive 'CCDC 793205' #TrackingRef '- amb1 cec2010 CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 N, C5 H3 N2 O4' _chemical_formula_sum 'C14 H17 N3 O4' _chemical_formula_weight 291.31 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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8377(3) _cell_length_b 8.6356(4) _cell_length_c 13.3174(7) _cell_angle_alpha 90.211(2) _cell_angle_beta 104.461(2) _cell_angle_gamma 109.951(2) _cell_volume 712.33(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5373 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 33.92 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9683 _exptl_absorpt_correction_T_max 0.9761 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; Amine and hydroxy H atoms were located and refined anisotropically. All H atoms bonded to carbons were calculated. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18329 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 33.92 _reflns_number_total 5373 _reflns_number_gt 4956 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _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 'Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191' _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^)+(0.0619P)^2^+0.1462P] 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 5373 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.12021(8) -0.05866(6) 0.87882(5) 0.01710(11) Uani 1 1 d . . . N1 N 0.14241(9) 0.50782(7) 0.88636(5) 0.01455(11) Uani 1 1 d . . . C1 C 0.29467(10) 0.44594(8) 0.87916(5) 0.01354(11) Uani 1 1 d . . . O2 O -0.31450(8) 0.07825(6) 0.92648(4) 0.01790(11) Uani 1 1 d . . . N2 N -0.02331(9) 0.37617(7) 0.89606(5) 0.01424(11) Uani 1 1 d . . . C2 C 0.22362(10) 0.27397(8) 0.88326(6) 0.01527(12) Uani 1 1 d . . . H2 H 0.3005 0.2019 0.8794 0.018 Uiso 1 1 calc R . . O3 O 0.52363(8) 0.71140(6) 0.86714(5) 0.02018(12) Uani 1 1 d . . . N3 N -0.21596(10) 0.13688(7) 0.16231(5) 0.01489(11) Uani 1 1 d . . . C3 C 0.01616(10) 0.23270(8) 0.89411(5) 0.01330(11) Uani 1 1 d . . . O4 O 0.65473(9) 0.50560(7) 0.87258(5) 0.02052(12) Uani 1 1 d . . . C4 C 0.50894(10) 0.55684(8) 0.87247(5) 0.01439(12) Uani 1 1 d . . . C5 C -0.15304(10) 0.07282(8) 0.90153(5) 0.01347(11) Uani 1 1 d . . . C6 C -0.19869(11) 0.12500(9) 0.27420(5) 0.01587(12) Uani 1 1 d . . . C7 C -0.35900(12) -0.00248(10) 0.30236(6) 0.02171(14) Uani 1 1 d . . . H7 H -0.4734 -0.0789 0.2503 0.026 Uiso 1 1 calc R . . C8 C -0.35067(15) -0.01729(12) 0.40726(7) 0.02759(17) Uani 1 1 d . . . H8 H -0.4588 -0.1044 0.4271 0.033 Uiso 1 1 calc R . . C9 C -0.18366(16) 0.09573(12) 0.48267(7) 0.02893(17) Uani 1 1 d . . . H9 H -0.1789 0.0877 0.5543 0.035 Uiso 1 1 calc R . . C10 C -0.02375(14) 0.22036(11) 0.45325(6) 0.02592(16) Uani 1 1 d . . . H10 H 0.0902 0.2965 0.5057 0.031 Uiso 1 1 calc R . . C11 C -0.02494(12) 0.23748(9) 0.34848(6) 0.01915(13) Uani 1 1 d . . . C12 C 0.15988(13) 0.37055(10) 0.32141(6) 0.02216(14) Uani 1 1 d . . . H12 H 0.1320 0.3622 0.2439 0.027 Uiso 1 1 calc R . . C13 C 0.37307(14) 0.34273(14) 0.36788(8) 0.03259(19) Uani 1 1 d . . . H13A H 0.3991 0.3433 0.4437 0.049 Uiso 1 1 calc R . . H13B H 0.4918 0.4314 0.3513 0.049 Uiso 1 1 calc R . . H13C H 0.3645 0.2358 0.3383 0.049 Uiso 1 1 calc R . . C14 C 0.17445(18) 0.54349(12) 0.35779(8) 0.0340(2) Uani 1 1 d . . . H14A H 0.0362 0.5578 0.3277 0.051 Uiso 1 1 calc R . . H14B H 0.2887 0.6272 0.3349 0.051 Uiso 1 1 calc R . . H14C H 0.2078 0.5562 0.4340 0.051 Uiso 1 1 calc R . . H3 H -0.144(2) 0.3914(18) 0.9006(11) 0.036(3) Uiso 1 1 d . . . H1 H -0.187(2) 0.2448(16) 0.1459(10) 0.026(3) Uiso 1 1 d . . . H4 H -0.345(2) 0.0766(16) 0.1268(10) 0.024(3) Uiso 1 1 d . . . H5 H -0.120(2) 0.1004(16) 0.1415(10) 0.028(3) Uiso 1 1 d . . . H6 H 0.669(3) 0.787(2) 0.8723(14) 0.055(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0123(2) 0.0092(2) 0.0311(3) 0.00105(17) 0.00943(18) 0.00282(16) N1 0.0095(2) 0.0095(2) 0.0258(3) 0.00274(19) 0.00685(19) 0.00335(18) C1 0.0098(2) 0.0093(2) 0.0230(3) 0.0021(2) 0.0067(2) 0.00349(19) O2 0.0122(2) 0.0145(2) 0.0294(3) 0.00135(18) 0.01064(19) 0.00396(17) N2 0.0093(2) 0.0096(2) 0.0256(3) 0.00240(19) 0.00736(19) 0.00354(18) C2 0.0116(2) 0.0092(2) 0.0275(3) 0.0022(2) 0.0088(2) 0.0043(2) O3 0.0115(2) 0.0092(2) 0.0415(3) 0.00496(19) 0.0102(2) 0.00348(17) N3 0.0130(2) 0.0138(2) 0.0192(2) 0.00071(19) 0.00447(19) 0.00623(19) C3 0.0101(2) 0.0086(2) 0.0221(3) 0.0016(2) 0.0065(2) 0.00293(19) O4 0.0144(2) 0.0171(2) 0.0367(3) 0.0079(2) 0.0132(2) 0.00925(19) C4 0.0107(2) 0.0111(3) 0.0227(3) 0.0030(2) 0.0064(2) 0.0042(2) C5 0.0099(2) 0.0102(2) 0.0202(3) 0.0016(2) 0.0054(2) 0.00253(19) C6 0.0146(3) 0.0158(3) 0.0194(3) 0.0016(2) 0.0063(2) 0.0069(2) C7 0.0173(3) 0.0211(3) 0.0268(3) 0.0030(3) 0.0087(3) 0.0050(3) C8 0.0259(4) 0.0290(4) 0.0303(4) 0.0079(3) 0.0155(3) 0.0071(3) C9 0.0314(4) 0.0352(4) 0.0234(3) 0.0061(3) 0.0135(3) 0.0113(3) C10 0.0259(4) 0.0291(4) 0.0206(3) -0.0003(3) 0.0071(3) 0.0064(3) C11 0.0179(3) 0.0192(3) 0.0200(3) -0.0001(2) 0.0055(2) 0.0058(2) C12 0.0185(3) 0.0207(3) 0.0220(3) -0.0002(2) 0.0041(2) 0.0012(3) C13 0.0189(4) 0.0432(5) 0.0309(4) 0.0036(4) 0.0046(3) 0.0065(3) C14 0.0391(5) 0.0205(4) 0.0328(4) -0.0034(3) 0.0045(4) 0.0024(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 O1 C5 1.2792(8) . ? N1 N2 1.3372(8) . ? N1 C1 1.3445(8) . ? C1 C2 1.4021(9) . ? C1 C4 1.4764(9) . ? O2 C5 1.2449(8) . ? N2 C3 1.3565(8) . ? N2 H3 0.895(15) . ? C2 C3 1.3849(9) . ? C2 H2 0.9500 . ? O3 C4 1.3074(8) . ? O3 H6 0.972(18) . ? N3 C6 1.4718(9) . ? N3 H1 0.923(13) . ? N3 H4 0.864(13) . ? N3 H5 0.916(13) . ? C3 C5 1.4909(9) . ? O4 C4 1.2207(8) . ? C6 C7 1.3925(10) . ? C6 C11 1.3971(10) . ? C7 C8 1.3919(12) . ? C7 H7 0.9500 . ? C8 C9 1.3873(13) . ? C8 H8 0.9500 . ? C9 C10 1.3861(13) . ? C9 H9 0.9500 . ? C10 C11 1.4020(11) . ? C10 H10 0.9500 . ? C11 C12 1.5123(11) . ? C12 C14 1.5310(13) . ? C12 C13 1.5347(13) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 N2 N1 C1 104.44(5) . . ? N1 C1 C2 111.64(6) . . ? N1 C1 C4 120.50(6) . . ? C2 C1 C4 127.81(6) . . ? N1 N2 C3 113.02(5) . . ? N1 N2 H3 118.4(10) . . ? C3 N2 H3 128.6(10) . . ? C3 C2 C1 104.50(5) . . ? C3 C2 H2 127.8 . . ? C1 C2 H2 127.8 . . ? C4 O3 H6 113.4(10) . . ? C6 N3 H1 111.6(8) . . ? C6 N3 H4 109.3(8) . . ? H1 N3 H4 109.2(11) . . ? C6 N3 H5 111.8(8) . . ? H1 N3 H5 106.7(11) . . ? H4 N3 H5 108.1(11) . . ? N2 C3 C2 106.40(5) . . ? N2 C3 C5 120.29(6) . . ? C2 C3 C5 133.31(6) . . ? O4 C4 O3 124.85(6) . . ? O4 C4 C1 121.95(6) . . ? O3 C4 C1 113.20(6) . . ? O2 C5 O1 125.89(6) . . ? O2 C5 C3 117.90(6) . . ? O1 C5 C3 116.18(6) . . ? C7 C6 C11 121.92(7) . . ? C7 C6 N3 117.66(6) . . ? C11 C6 N3 120.41(6) . . ? C8 C7 C6 119.65(7) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 119.70(8) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 119.85(8) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 122.03(8) . . ? C9 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C6 C11 C10 116.80(7) . . ? C6 C11 C12 123.56(7) . . ? C10 C11 C12 119.61(7) . . ? C11 C12 C14 111.29(7) . . ? C11 C12 C13 110.37(7) . . ? C14 C12 C13 111.03(7) . . ? C11 C12 H12 108.0 . . ? C14 C12 H12 108.0 . . ? C13 C12 H12 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H3 O4 0.895(15) 1.918(15) 2.7443(7) 152.8(13) 1_455 N3 H1 N1 0.923(13) 2.114(13) 3.0350(8) 175.4(12) 2_566 N3 H4 O2 0.864(13) 2.183(13) 3.0290(8) 166.3(11) 2_456 N3 H5 O1 0.916(13) 1.877(14) 2.7795(8) 168.0(12) 2_556 O3 H6 O1 0.972(18) 1.576(18) 2.5311(7) 166.4(17) 1_665 _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.564 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.051 data_Compound-5 _database_code_depnum_ccdc_archive 'CCDC 793206' #TrackingRef '- amb1 cec2010 CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 N2 O2, 2(C5 H3 N2 O4)' _chemical_formula_sum 'C18 H26 N6 O10' _chemical_formula_weight 486.45 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0986(2) _cell_length_b 7.1127(2) _cell_length_c 10.4660(2) _cell_angle_alpha 98.2910(10) _cell_angle_beta 92.7330(10) _cell_angle_gamma 98.1900(10) _cell_volume 516.32(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3892 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 33.81 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9570 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details 'SADABS. G. Sheldrick (1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART APEX II' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13245 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 33.81 _reflns_number_total 3892 _reflns_number_gt 3697 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II' _computing_cell_refinement 'APEX II' _computing_data_reduction 'APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED, L. Barbour (1999); http://x-seed.net/' _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^)+(0.0553P)^2^+0.1292P] 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 3892 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.01260(7) -0.11986(8) 0.83374(5) 0.01627(11) Uani 1 1 d . . . N1 N 0.27375(8) 0.13415(8) 0.98639(5) 0.01100(10) Uani 1 1 d . . . C1 C 0.45877(9) 0.16977(9) 0.82632(6) 0.01047(11) Uani 1 1 d . . . H1 H 0.5086 0.1648 0.7434 0.013 Uiso 1 1 calc R . . O2 O 0.14084(7) -0.07608(7) 0.65578(5) 0.01386(10) Uani 1 1 d . . . N2 N 0.43383(8) 0.24276(8) 1.04279(5) 0.01110(10) Uani 1 1 d . . . C2 C 0.28170(8) 0.08574(9) 0.85660(6) 0.00985(10) Uani 1 1 d . . . O3 O 0.85295(7) 0.37263(8) 0.88061(5) 0.01495(10) Uani 1 1 d . . . N3 N 0.12071(7) 0.35002(8) 0.47519(5) 0.00940(10) Uani 1 1 d . . . C3 C 0.54814(8) 0.26382(9) 0.94530(6) 0.00974(10) Uani 1 1 d . . . O4 O 0.79021(7) 0.45106(7) 1.08872(5) 0.01335(10) Uani 1 1 d . . . C4 C 0.74377(9) 0.36796(9) 0.96870(6) 0.01038(11) Uani 1 1 d . . . O5 O 0.48506(7) 0.35226(8) 0.31750(5) 0.01562(10) Uani 1 1 d . . . C5 C 0.12327(9) -0.04627(9) 0.77690(6) 0.01046(11) Uani 1 1 d . . . C6 C 0.03859(9) 0.39625(9) 0.60291(6) 0.01125(11) Uani 1 1 d . . . H6A H 0.1306 0.4934 0.6604 0.014 Uiso 1 1 calc R . . H6B H 0.0173 0.2789 0.6442 0.014 Uiso 1 1 calc R . . C7 C 0.14864(9) 0.52717(9) 0.41270(6) 0.01128(11) Uani 1 1 d . . . H7A H 0.1991 0.4972 0.3268 0.014 Uiso 1 1 calc R . . H7B H 0.2431 0.6266 0.4665 0.014 Uiso 1 1 calc R . . C8 C 0.30153(9) 0.26761(9) 0.49565(6) 0.01128(11) Uani 1 1 d . . . H8A H 0.2740 0.1594 0.5451 0.014 Uiso 1 1 calc R . . H8B H 0.3958 0.3674 0.5492 0.014 Uiso 1 1 calc R . . C9 C 0.39053(9) 0.19643(9) 0.37260(6) 0.01317(11) Uani 1 1 d . . . H9A H 0.4831 0.1110 0.3921 0.016 Uiso 1 1 calc R . . H9B H 0.2899 0.1207 0.3094 0.016 Uiso 1 1 calc R . . H10 H 0.1760(19) 0.1073(18) 1.0367(12) 0.024(3) Uiso 1 1 d . . . H3 H 0.475(2) 0.317(2) 0.2313(15) 0.036(4) Uiso 1 1 d . . . H2 H 0.913(2) 0.506(2) 1.0924(15) 0.044(4) Uiso 1 1 d . . . H4 H 0.029(2) 0.250(2) 0.4201(13) 0.028(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0116(2) 0.0205(2) 0.0139(2) -0.00009(17) 0.00270(16) -0.00500(17) N1 0.0086(2) 0.0130(2) 0.0098(2) -0.00006(17) 0.00045(16) -0.00201(17) C1 0.0091(2) 0.0118(2) 0.0094(2) -0.00033(18) 0.00066(18) -0.00025(18) O2 0.0133(2) 0.0158(2) 0.0099(2) -0.00058(16) -0.00002(15) -0.00377(16) N2 0.0086(2) 0.0132(2) 0.0100(2) 0.00014(17) 0.00007(16) -0.00183(17) C2 0.0088(2) 0.0105(2) 0.0091(2) -0.00025(18) -0.00026(17) -0.00044(18) O3 0.0099(2) 0.0216(2) 0.0109(2) -0.00056(17) 0.00174(15) -0.00318(17) N3 0.0086(2) 0.0103(2) 0.0086(2) 0.00060(16) 0.00049(16) 0.00005(16) C3 0.0077(2) 0.0109(2) 0.0096(2) 0.00027(18) 0.00016(17) -0.00052(18) O4 0.0096(2) 0.0183(2) 0.00951(19) -0.00173(16) -0.00032(15) -0.00250(16) C4 0.0088(2) 0.0115(2) 0.0100(2) 0.00069(18) -0.00044(18) 0.00000(18) O5 0.0152(2) 0.0186(2) 0.0109(2) -0.00131(17) 0.00278(16) -0.00144(17) C5 0.0090(2) 0.0104(2) 0.0107(2) -0.00024(18) -0.00059(18) -0.00039(18) C6 0.0115(2) 0.0142(2) 0.0084(2) 0.00217(18) 0.00191(18) 0.00236(19) C7 0.0102(2) 0.0123(2) 0.0118(2) 0.00353(19) 0.00250(18) 0.00090(19) C8 0.0093(2) 0.0129(2) 0.0114(2) 0.00109(19) 0.00000(18) 0.00180(19) C9 0.0113(2) 0.0139(3) 0.0129(3) -0.0019(2) 0.00036(19) 0.0015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.2485(8) . ? N1 N2 1.3382(7) . ? N1 C2 1.3583(8) . ? N1 H10 0.906(13) . ? C1 C2 1.3842(8) . ? C1 C3 1.4015(8) . ? C1 H1 0.9500 . ? O2 C5 1.2698(7) . ? N2 C3 1.3455(8) . ? C2 C5 1.4920(8) . ? O3 C4 1.2334(7) . ? N3 C7 1.4945(8) . ? N3 C6 1.4957(8) . ? N3 C8 1.5038(8) . ? N3 H4 0.991(15) . ? C3 C4 1.4695(9) . ? O4 C4 1.3141(7) . ? O4 H2 0.902(18) . ? O5 C9 1.4215(8) . ? O5 H3 0.897(15) . ? C6 C7 1.5169(9) 2_566 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C6 1.5169(9) 2_566 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5149(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? 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 N2 N1 C2 112.70(5) . . ? N2 N1 H10 118.0(8) . . ? C2 N1 H10 129.3(8) . . ? C2 C1 C3 104.54(5) . . ? C2 C1 H1 127.7 . . ? C3 C1 H1 127.7 . . ? N1 N2 C3 104.65(5) . . ? N1 C2 C1 106.57(5) . . ? N1 C2 C5 121.18(5) . . ? C1 C2 C5 132.10(6) . . ? C7 N3 C6 108.87(5) . . ? C7 N3 C8 113.45(5) . . ? C6 N3 C8 109.11(5) . . ? C7 N3 H4 109.4(8) . . ? C6 N3 H4 108.2(8) . . ? C8 N3 H4 107.6(8) . . ? N2 C3 C1 111.54(5) . . ? N2 C3 C4 121.55(5) . . ? C1 C3 C4 126.87(6) . . ? C4 O4 H2 107.1(10) . . ? O3 C4 O4 124.12(6) . . ? O3 C4 C3 121.10(6) . . ? O4 C4 C3 114.78(5) . . ? C9 O5 H3 107.4(10) . . ? O1 C5 O2 125.58(6) . . ? O1 C5 C2 118.13(6) . . ? O2 C5 C2 116.28(5) . . ? N3 C6 C7 111.35(5) . 2_566 ? N3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 2_566 . ? N3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 2_566 . ? H6A C6 H6B 108.0 . . ? N3 C7 C6 110.50(5) . 2_566 ? N3 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 2_566 . ? N3 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 2_566 . ? H7A C7 H7B 108.1 . . ? N3 C8 C9 114.82(5) . . ? N3 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? N3 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.5 . . ? O5 C9 C8 111.13(5) . . ? O5 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? O5 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.629 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.055 data_Compound-6 _database_code_depnum_ccdc_archive 'CCDC 793207' #TrackingRef '- amb1 cec2010 CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H18 N2, 2(C5 H3 N2 O4)' _chemical_formula_sum 'C16 H24 N6 O8' _chemical_formula_weight 428.41 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/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.7326(6) _cell_length_b 13.6932(6) _cell_length_c 8.1323(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.992(2) _cell_angle_gamma 90.00 _cell_volume 1860.76(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6504 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 28.88 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9784 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16954 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 29.25 _reflns_number_total 2493 _reflns_number_gt 1921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0437P)^2^+1.1419P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2493 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0850 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.49223(5) 0.13721(6) 0.02791(11) 0.0131(2) Uani 1 1 d . . . O2 O 0.39842(5) 0.24184(6) 0.09948(11) 0.0147(2) Uani 1 1 d . . . O3 O 0.23724(5) -0.17347(7) 0.35074(11) 0.0140(2) Uani 1 1 d . . . H3A H 0.1900(12) -0.2026(15) 0.383(2) 0.054(6) Uiso 1 1 d . . . O4 O 0.16765(5) -0.03349(7) 0.36224(11) 0.0162(2) Uani 1 1 d . . . N1 N 0.40803(6) -0.01829(8) 0.14713(13) 0.0126(2) Uani 1 1 d . . . H1 H 0.4542 -0.0337 0.1069 0.015 Uiso 1 1 calc R . . N2 N 0.35915(6) -0.08365(8) 0.21026(13) 0.0131(2) Uani 1 1 d . . . N3 N 0.06729(6) 0.19544(7) 0.44326(12) 0.0108(2) Uani 1 1 d . . . H3B H 0.0427 0.2530 0.4740 0.013 Uiso 1 1 calc R . . C1 C 0.42589(7) 0.15729(9) 0.08801(15) 0.0105(3) Uani 1 1 d . . . C2 C 0.37952(7) 0.07422(9) 0.15114(15) 0.0106(3) Uani 1 1 d . . . C3 C 0.30687(7) 0.06884(9) 0.22212(15) 0.0117(3) Uani 1 1 d . . . H3 H 0.2713 0.1210 0.2428 0.014 Uiso 1 1 calc R . . C4 C 0.29688(7) -0.03059(9) 0.25739(14) 0.0110(3) Uani 1 1 d . . . C5 C 0.22763(7) -0.07800(9) 0.32984(14) 0.0111(3) Uani 1 1 d . . . C6 C 0.15527(7) 0.20837(10) 0.46997(16) 0.0135(3) Uani 1 1 d . . . H6A H 0.1743 0.2550 0.3894 0.020 Uiso 1 1 calc R . . H6B H 0.1820 0.1454 0.4567 0.020 Uiso 1 1 calc R . . H6C H 0.1675 0.2332 0.5815 0.020 Uiso 1 1 calc R . . C7 C 0.04009(8) 0.11595(10) 0.55132(16) 0.0141(3) Uani 1 1 d . . . H7A H 0.0570 0.1304 0.6660 0.021 Uiso 1 1 calc R . . H7B H 0.0638 0.0539 0.5185 0.021 Uiso 1 1 calc R . . H7C H -0.0184 0.1111 0.5408 0.021 Uiso 1 1 calc R . . C8 C 0.04547(7) 0.17778(10) 0.26564(15) 0.0132(3) Uani 1 1 d . . . H8A H 0.0674 0.1141 0.2321 0.016 Uiso 1 1 calc R . . H8B H 0.0693 0.2294 0.1984 0.016 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 0.0112(4) 0.0104(5) 0.0182(5) -0.0006(4) 0.0062(3) 0.0004(3) O2 0.0128(5) 0.0093(5) 0.0225(5) -0.0002(4) 0.0049(4) 0.0013(3) O3 0.0126(5) 0.0102(5) 0.0195(5) 0.0019(4) 0.0048(4) -0.0019(4) O4 0.0129(5) 0.0136(5) 0.0227(5) -0.0018(4) 0.0064(4) 0.0001(4) N1 0.0100(5) 0.0098(6) 0.0184(5) 0.0012(4) 0.0050(4) -0.0002(4) N2 0.0121(5) 0.0108(6) 0.0168(5) 0.0015(4) 0.0050(4) -0.0014(4) N3 0.0108(5) 0.0091(5) 0.0124(5) -0.0005(4) 0.0014(4) 0.0005(4) C1 0.0101(6) 0.0103(6) 0.0114(6) -0.0010(5) 0.0011(5) 0.0002(5) C2 0.0108(6) 0.0090(6) 0.0122(6) -0.0011(5) 0.0011(5) 0.0005(5) C3 0.0115(6) 0.0106(6) 0.0131(6) -0.0015(5) 0.0022(5) 0.0006(5) C4 0.0105(6) 0.0117(6) 0.0110(6) -0.0011(5) 0.0004(5) -0.0011(5) C5 0.0118(6) 0.0108(6) 0.0107(6) -0.0018(5) 0.0013(5) -0.0021(5) C6 0.0101(6) 0.0137(7) 0.0167(6) 0.0003(5) -0.0001(5) -0.0002(5) C7 0.0143(6) 0.0133(7) 0.0150(6) 0.0024(5) 0.0040(5) 0.0004(5) C8 0.0135(6) 0.0160(7) 0.0100(6) 0.0000(5) 0.0011(5) 0.0013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2662(15) . ? O2 C1 1.2510(15) . ? O3 C5 1.3269(16) . ? O3 H3A 0.93(2) . ? O4 C5 1.2149(15) . ? N1 N2 1.3331(14) . ? N1 C2 1.3546(16) . ? N1 H1 0.8800 . ? N2 C4 1.3424(16) . ? N3 C7 1.4852(16) . ? N3 C6 1.4873(15) . ? N3 C8 1.4910(15) . ? N3 H3B 0.9300 . ? C1 C2 1.4836(17) . ? C2 C3 1.3746(17) . ? C3 C4 1.4032(18) . ? C3 H3 0.9500 . ? C4 C5 1.4774(17) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C8 1.530(2) 2 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? 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 C5 O3 H3A 110.9(12) . . ? N2 N1 C2 113.24(10) . . ? N2 N1 H1 123.4 . . ? C2 N1 H1 123.4 . . ? N1 N2 C4 104.33(10) . . ? C7 N3 C6 109.41(10) . . ? C7 N3 C8 112.79(10) . . ? C6 N3 C8 110.56(10) . . ? C7 N3 H3B 108.0 . . ? C6 N3 H3B 108.0 . . ? C8 N3 H3B 108.0 . . ? O2 C1 O1 124.24(11) . . ? O2 C1 C2 118.88(11) . . ? O1 C1 C2 116.87(11) . . ? N1 C2 C3 106.28(10) . . ? N1 C2 C1 121.16(11) . . ? C3 C2 C1 132.55(11) . . ? C2 C3 C4 104.78(11) . . ? C2 C3 H3 127.6 . . ? C4 C3 H3 127.6 . . ? N2 C4 C3 111.36(11) . . ? N2 C4 C5 120.84(12) . . ? C3 C4 C5 127.75(11) . . ? O4 C5 O3 124.23(11) . . ? O4 C5 C4 122.69(12) . . ? O3 C5 C4 113.06(11) . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C8 110.63(12) . 2 ? N3 C8 H8A 109.5 . . ? C8 C8 H8A 109.5 2 . ? N3 C8 H8B 109.5 . . ? C8 C8 H8B 109.5 2 . ? H8A C8 H8B 108.1 . . ? 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 C2 N1 N2 C4 -0.30(14) . . . . ? N2 N1 C2 C3 0.06(14) . . . . ? N2 N1 C2 C1 179.34(11) . . . . ? O2 C1 C2 N1 -177.55(11) . . . . ? O1 C1 C2 N1 1.26(17) . . . . ? O2 C1 C2 C3 1.5(2) . . . . ? O1 C1 C2 C3 -179.69(12) . . . . ? N1 C2 C3 C4 0.19(13) . . . . ? C1 C2 C3 C4 -178.96(13) . . . . ? N1 N2 C4 C3 0.42(13) . . . . ? N1 N2 C4 C5 178.07(10) . . . . ? C2 C3 C4 N2 -0.39(14) . . . . ? C2 C3 C4 C5 -177.84(12) . . . . ? N2 C4 C5 O4 -174.21(11) . . . . ? C3 C4 C5 O4 3.0(2) . . . . ? N2 C4 C5 O3 4.00(16) . . . . ? C3 C4 C5 O3 -178.77(11) . . . . ? C7 N3 C8 C8 64.54(9) . . . 2 ? C6 N3 C8 C8 -172.60(7) . . . 2 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.285 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.056 data_Compound-7 _database_code_depnum_ccdc_archive 'CCDC 793208' #TrackingRef '- amb1 cec2010 CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H18 N2, 2(C5 H3 N2 O4) ' _chemical_formula_sum 'C16 H24 N6 O8' _chemical_formula_weight 428.41 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.5537(6) _cell_length_b 9.3845(11) _cell_length_c 11.1398(14) _cell_angle_alpha 79.342(4) _cell_angle_beta 85.338(5) _cell_angle_gamma 85.904(4) _cell_volume 465.52(10) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4768 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 29.56 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 226 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9725 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12441 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 29.74 _reflns_number_total 2637 _reflns_number_gt 2210 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0480P)^2^+0.1456P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2637 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 -0.08752(18) 0.13084(8) 0.56858(7) 0.01475(18) Uani 1 1 d . . . O2 O -0.40110(18) 0.30964(8) 0.48625(7) 0.01668(18) Uani 1 1 d . . . O3 O 0.42372(18) 0.36322(8) 0.91918(7) 0.01602(18) Uani 1 1 d . . . H3 H 0.5253 0.3841 0.9725 0.024 Uiso 1 1 calc R . . O4 O 0.24057(18) 0.59344(8) 0.91187(7) 0.01512(18) Uani 1 1 d . . . N1 N -0.2247(2) 0.48775(10) 0.64025(8) 0.01230(19) Uani 1 1 d . . . H1 H -0.3593 0.5306 0.5912 0.015 Uiso 1 1 calc R . . N2 N -0.1105(2) 0.55187(10) 0.72241(8) 0.01261(19) Uani 1 1 d . . . N3 N 0.6699(2) 0.86008(10) 0.64426(8) 0.01254(19) Uani 1 1 d . . . H3A H 0.7696 0.9383 0.6058 0.019 Uiso 1 1 calc R . . H3B H 0.5684 0.8266 0.5891 0.019 Uiso 1 1 calc R . . H3C H 0.8003 0.7888 0.6780 0.019 Uiso 1 1 calc R . . C1 C -0.1115(2) 0.35003(11) 0.64053(9) 0.0112(2) Uani 1 1 d . . . C2 C 0.0899(2) 0.32180(11) 0.72885(10) 0.0123(2) Uani 1 1 d . . . H2 H 0.2080 0.2349 0.7519 0.015 Uiso 1 1 calc R . . C3 C 0.0818(2) 0.44975(11) 0.77717(9) 0.0115(2) Uani 1 1 d . . . C4 C -0.2070(2) 0.25590(11) 0.55860(9) 0.0109(2) Uani 1 1 d . . . C5 C 0.2545(2) 0.47695(11) 0.87556(10) 0.0124(2) Uani 1 1 d . . . C6 C 0.4594(2) 0.90358(12) 0.74236(10) 0.0128(2) Uani 1 1 d . . . H6A H 0.3321 0.8225 0.7767 0.015 Uiso 1 1 calc R . . H6B H 0.3311 0.9881 0.7071 0.015 Uiso 1 1 calc R . . C7 C 0.6250(2) 0.94279(12) 0.84373(10) 0.0139(2) Uani 1 1 d . . . H7A H 0.7430 1.0275 0.8098 0.017 Uiso 1 1 calc R . . H7B H 0.7630 0.8603 0.8747 0.017 Uiso 1 1 calc R . . C8 C 0.4171(2) 0.97898(12) 0.94994(9) 0.0133(2) Uani 1 1 d . . . H8A H 0.2765 1.0602 0.9187 0.016 Uiso 1 1 calc R . . H8B H 0.3019 0.8936 0.9850 0.016 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 0.0177(4) 0.0110(4) 0.0163(4) -0.0045(3) -0.0025(3) 0.0005(3) O2 0.0201(4) 0.0152(4) 0.0170(4) -0.0064(3) -0.0091(3) 0.0020(3) O3 0.0195(4) 0.0133(4) 0.0170(4) -0.0044(3) -0.0102(3) 0.0017(3) O4 0.0188(4) 0.0124(4) 0.0159(4) -0.0053(3) -0.0060(3) -0.0003(3) N1 0.0147(4) 0.0116(4) 0.0119(4) -0.0042(3) -0.0050(3) 0.0001(3) N2 0.0148(4) 0.0128(4) 0.0117(4) -0.0046(3) -0.0044(3) -0.0006(3) N3 0.0151(4) 0.0124(4) 0.0113(4) -0.0044(3) -0.0025(3) -0.0007(3) C1 0.0127(5) 0.0104(4) 0.0111(5) -0.0034(4) -0.0013(4) -0.0007(4) C2 0.0133(5) 0.0111(5) 0.0131(5) -0.0032(4) -0.0026(4) -0.0002(4) C3 0.0126(5) 0.0119(4) 0.0107(5) -0.0030(4) -0.0022(4) -0.0015(4) C4 0.0125(5) 0.0115(5) 0.0096(4) -0.0038(4) -0.0003(4) -0.0026(4) C5 0.0129(5) 0.0129(5) 0.0116(5) -0.0023(4) -0.0016(4) -0.0020(4) C6 0.0139(5) 0.0142(5) 0.0110(5) -0.0045(4) -0.0012(4) -0.0002(4) C7 0.0154(5) 0.0170(5) 0.0104(5) -0.0047(4) -0.0021(4) -0.0011(4) C8 0.0156(5) 0.0146(5) 0.0104(5) -0.0039(4) -0.0013(4) 0.0004(4) _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 1.2476(13) . ? O2 C4 1.2595(13) . ? O3 C5 1.3117(13) . ? O3 H3 0.8400 . ? O4 C5 1.2297(13) . ? N1 N2 1.3400(12) . ? N1 C1 1.3563(13) . ? N1 H1 0.8800 . ? N2 C3 1.3448(14) . ? N3 C6 1.4895(14) . ? N3 H3A 0.9100 . ? N3 H3B 0.9100 . ? N3 H3C 0.9100 . ? C1 C2 1.3766(14) . ? C1 C4 1.4901(14) . ? C2 C3 1.4008(14) . ? C2 H2 0.9500 . ? C3 C5 1.4687(14) . ? C6 C7 1.5200(14) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5271(15) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C8 1.521(2) 2_677 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? 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 C5 O3 H3 109.5 . . ? N2 N1 C1 113.08(9) . . ? N2 N1 H1 123.5 . . ? C1 N1 H1 123.5 . . ? N1 N2 C3 103.99(9) . . ? C6 N3 H3A 109.5 . . ? C6 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C6 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? N1 C1 C2 106.49(9) . . ? N1 C1 C4 123.03(9) . . ? C2 C1 C4 130.47(10) . . ? C1 C2 C3 104.61(9) . . ? C1 C2 H2 127.7 . . ? C3 C2 H2 127.7 . . ? N2 C3 C2 111.82(9) . . ? N2 C3 C5 121.31(9) . . ? C2 C3 C5 126.86(10) . . ? O1 C4 O2 126.16(10) . . ? O1 C4 C1 116.74(9) . . ? O2 C4 C1 117.11(9) . . ? O4 C5 O3 124.46(10) . . ? O4 C5 C3 123.38(10) . . ? O3 C5 C3 112.15(9) . . ? N3 C6 C7 110.61(9) . . ? N3 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C6 C7 C8 112.22(9) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C8 C8 C7 112.10(11) 2_677 . ? C8 C8 H8A 109.2 2_677 . ? C7 C8 H8A 109.2 . . ? C8 C8 H8B 109.2 2_677 . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? 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 C1 N1 N2 C3 -0.31(12) . . . . ? N2 N1 C1 C2 0.10(13) . . . . ? N2 N1 C1 C4 179.09(9) . . . . ? N1 C1 C2 C3 0.14(12) . . . . ? C4 C1 C2 C3 -178.74(11) . . . . ? N1 N2 C3 C2 0.39(12) . . . . ? N1 N2 C3 C5 -179.44(9) . . . . ? C1 C2 C3 N2 -0.34(12) . . . . ? C1 C2 C3 C5 179.49(10) . . . . ? N1 C1 C4 O1 -179.40(10) . . . . ? C2 C1 C4 O1 -0.69(17) . . . . ? N1 C1 C4 O2 0.34(16) . . . . ? C2 C1 C4 O2 179.06(11) . . . . ? N2 C3 C5 O4 -1.72(17) . . . . ? C2 C3 C5 O4 178.47(11) . . . . ? N2 C3 C5 O3 178.41(10) . . . . ? C2 C3 C5 O3 -1.40(16) . . . . ? N3 C6 C7 C8 -176.45(9) . . . . ? C6 C7 C8 C8 -178.88(11) . . . 2_677 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.433 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.054