# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'T M Klapotke' _publ_contact_author_email TMK@CUP.UNI-MUENCHEN.DE _publ_section_title ; Synthesis and properties of 5-nitrotetrazole derivatives as new energetic materials ; loop_ _publ_author_name 'T M Klapotke' 'Matthias Rasp' 'Carles Miro Sabate' data_dx098-NTAN _database_code_depnum_ccdc_archive 'CCDC 704402' _audit_creation_date 2008-09-01T14:27:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C3 H2 N6 O2' _chemical_formula_sum 'C3 H2 N6 O2' _chemical_formula_weight 154.11 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.4521(3) _cell_length_b 6.1470(3) _cell_length_c 17.4832(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 585.93(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4260 _cell_measurement_theta_min 3.7342 _cell_measurement_theta_max 29.9987 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.941 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Oxford Xcalibur3 CCD area detector' _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_reflns_number 7761 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 30.10 _reflns_number_total 1036 _reflns_number_gt 896 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.10 _diffrn_measured_fraction_theta_full 0.996 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0338P)^2^+0.4333P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1033 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0622 _refine_ls_wR_factor_gt 0.0563 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.212 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.046 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 O2 O -0.0748(2) 0.04824(19) 0.34568(6) 0.0199(2) Uani 1 1 d . . . O1 O 0.2311(2) -0.13448(19) 0.39350(6) 0.0215(3) Uani 1 1 d . . . N5 N 0.1358(2) 0.0344(2) 0.20515(7) 0.0120(2) Uani 1 1 d . . . N4 N 0.3019(2) -0.02001(19) 0.15331(7) 0.0120(2) Uani 1 1 d . . . N1 N 0.1214(2) -0.0466(2) 0.34082(7) 0.0143(2) Uani 1 1 d . . . N2 N 0.4455(2) -0.1631(2) 0.25364(7) 0.0148(3) Uani 1 1 d . . . N3 N 0.4883(2) -0.1377(2) 0.17999(7) 0.0152(3) Uani 1 1 d . . . N6 N -0.1314(3) -0.0745(2) 0.01441(8) 0.0208(3) Uani 1 1 d . . . C2 C 0.2869(3) 0.0470(3) 0.07310(8) 0.0147(3) Uani 1 1 d . . . C3 C 0.0524(3) -0.0251(3) 0.03997(8) 0.0149(3) Uani 1 1 d . . . C1 C 0.2341(3) -0.0586(2) 0.26587(8) 0.0122(3) Uani 1 1 d . . . H1 H 0.426(3) -0.020(3) 0.0466(9) 0.013(4) Uiso 1 1 d . . . H2 H 0.296(4) 0.211(3) 0.0706(11) 0.028(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 O2 0.0195(6) 0.0205(5) 0.0197(5) 0.0004(5) 0.0038(5) 0.0042(5) O1 0.0277(6) 0.0234(5) 0.0133(5) 0.0056(5) -0.0056(5) -0.0004(6) N5 0.0123(6) 0.0113(5) 0.0125(5) -0.0010(5) -0.0001(4) -0.0018(5) N4 0.0115(5) 0.0115(5) 0.0129(5) -0.0006(5) 0.0000(5) -0.0002(5) N1 0.0184(6) 0.0111(5) 0.0135(5) -0.0001(5) -0.0011(5) -0.0022(5) N2 0.0154(6) 0.0128(6) 0.0162(6) 0.0005(5) -0.0013(5) 0.0000(5) N3 0.0151(6) 0.0133(5) 0.0172(6) -0.0004(5) -0.0011(5) 0.0018(5) N6 0.0191(7) 0.0242(7) 0.0190(6) -0.0010(6) -0.0010(5) 0.0001(6) C2 0.0150(7) 0.0167(6) 0.0126(6) 0.0014(6) 0.0004(5) -0.0013(7) C3 0.0182(7) 0.0145(7) 0.0120(6) -0.0004(6) 0.0005(6) 0.0019(6) C1 0.0128(6) 0.0096(6) 0.0142(6) -0.0008(5) -0.0016(5) -0.0020(6) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 O2 N1 1.2211(16) . ? O1 N1 1.2239(16) . ? N5 C1 1.3192(18) . ? N5 N4 1.3242(16) . ? N4 N3 1.3318(16) . ? N4 C2 1.4640(19) . ? N1 C1 1.4489(18) . ? N2 N3 1.3178(18) . ? N2 C1 1.3367(19) . ? N6 C3 1.138(2) . ? C2 C3 1.472(2) . ? C2 H1 0.977(17) . ? C2 H2 1.007(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N5 N4 99.43(12) . . ? N5 N4 N3 114.79(11) . . ? N5 N4 C2 123.11(12) . . ? N3 N4 C2 122.08(12) . . ? O2 N1 O1 125.89(13) . . ? O2 N1 C1 117.30(12) . . ? O1 N1 C1 116.81(12) . . ? N3 N2 C1 104.62(12) . . ? N2 N3 N4 105.74(12) . . ? N4 C2 C3 109.92(12) . . ? N4 C2 H1 107.0(10) . . ? C3 C2 H1 111.0(10) . . ? N4 C2 H2 108.6(11) . . ? C3 C2 H2 109.1(11) . . ? H1 C2 H2 111.1(15) . . ? N6 C3 C2 177.90(17) . . ? N5 C1 N2 115.43(13) . . ? N5 C1 N1 122.25(13) . . ? N2 C1 N1 122.32(12) . . ? 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 N5 N4 N3 0.06(15) . . . . ? C1 N5 N4 C2 -178.64(13) . . . . ? C1 N2 N3 N4 0.27(15) . . . . ? N5 N4 N3 N2 -0.22(16) . . . . ? C2 N4 N3 N2 178.50(13) . . . . ? N5 N4 C2 C3 -56.50(17) . . . . ? N3 N4 C2 C3 124.89(14) . . . . ? N4 N5 C1 N2 0.12(16) . . . . ? N4 N5 C1 N1 179.63(12) . . . . ? N3 N2 C1 N5 -0.26(17) . . . . ? N3 N2 C1 N1 -179.76(13) . . . . ? O2 N1 C1 N5 2.2(2) . . . . ? O1 N1 C1 N5 -178.37(13) . . . . ? O2 N1 C1 N2 -178.29(13) . . . . ? O1 N1 C1 N2 1.1(2) . . . . ? data_dx100-NTTz_H2O _database_code_depnum_ccdc_archive 'CCDC 704403' _audit_creation_date 2008-09-01T16:43:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C3 H3 N9 O2, H2 O' _chemical_formula_sum 'C3 H5 N9 O3' _chemical_formula_weight 215.16 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.3238(5) _cell_length_b 4.9208(4) _cell_length_c 13.0318(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.132(9) _cell_angle_gamma 90.00 _cell_volume 397.90(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1952 _cell_measurement_theta_min 4.1027 _cell_measurement_theta_max 29.9989 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Oxford Xcalibur3 CCD area detector' _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_reflns_number 5172 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 30.09 _reflns_number_total 1273 _reflns_number_gt 952 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.09 _diffrn_measured_fraction_theta_full 0.991 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0338P)^2^+0.4333P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1273 _refine_ls_number_parameters 156 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0589 _refine_ls_wR_factor_gt 0.0503 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.262 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.061 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 O3 O -0.0143(3) 0.8471(4) 0.04917(14) 0.0204(4) Uani 1 1 d . . . O1 O 0.4307(2) 0.3388(3) 0.61919(12) 0.0185(4) Uani 1 1 d . . . O2 O 0.2481(3) 0.7053(3) 0.63614(13) 0.0195(4) Uani 1 1 d . . . N9 N 0.4482(3) 0.0680(4) 0.15220(16) 0.0133(5) Uani 1 1 d . . . N6 N 0.4501(3) 0.5049(4) 0.15777(16) 0.0140(4) Uani 1 1 d . . . N5 N 0.0981(3) 0.7250(4) 0.42654(15) 0.0148(4) Uani 1 1 d . . . N4 N 0.0582(3) 0.6585(4) 0.32681(15) 0.0157(4) Uani 1 1 d . . . N8 N 0.6207(3) 0.1513(4) 0.11427(15) 0.0155(4) Uani 1 1 d . . . N3 N 0.1660(3) 0.4290(4) 0.31986(15) 0.0129(4) Uani 1 1 d . . . N1 N 0.3087(3) 0.5224(4) 0.58455(16) 0.0145(4) Uani 1 1 d . . . N2 N 0.2761(3) 0.3385(4) 0.41042(13) 0.0125(4) Uani 1 1 d . . . N7 N 0.6213(3) 0.4151(4) 0.11786(16) 0.0151(5) Uani 1 1 d . . . C2 C 0.1450(3) 0.2790(5) 0.22192(17) 0.0136(4) Uani 1 1 d . . . C3 C 0.3466(3) 0.2856(5) 0.17867(15) 0.0116(4) Uani 1 1 d . . . C1 C 0.2277(3) 0.5284(5) 0.47313(19) 0.0125(4) Uani 1 1 d . . . H1 H 0.033(4) 0.375(5) 0.1749(18) 0.015(6) Uiso 1 1 d . . . H2 H 0.101(3) 0.101(5) 0.2342(17) 0.010(6) Uiso 1 1 d . . . H5 H -0.137(5) 0.865(6) 0.066(2) 0.041(9) Uiso 1 1 d . . . H4 H -0.010(5) 0.681(8) 0.025(3) 0.054(11) Uiso 1 1 d . . . H3 H 0.424(4) -0.106(6) 0.163(2) 0.035(9) 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 O3 0.0183(9) 0.0189(10) 0.0252(10) -0.0018(8) 0.0072(8) 0.0003(7) O1 0.0181(8) 0.0152(9) 0.0216(9) 0.0017(7) 0.0025(6) 0.0032(7) O2 0.0206(9) 0.0180(10) 0.0208(9) -0.0065(7) 0.0063(7) 0.0016(7) N9 0.0136(10) 0.0101(11) 0.0167(12) -0.0004(8) 0.0043(9) -0.0015(8) N6 0.0127(10) 0.0131(10) 0.0174(11) 0.0002(8) 0.0057(8) 0.0003(8) N5 0.0148(9) 0.0142(11) 0.0162(10) -0.0003(8) 0.0052(8) 0.0001(8) N4 0.0162(10) 0.0135(11) 0.0185(11) 0.0002(9) 0.0060(8) 0.0024(8) N8 0.0144(11) 0.0166(11) 0.0159(11) -0.0004(9) 0.0043(8) -0.0015(8) N3 0.0120(9) 0.0105(10) 0.0173(10) 0.0017(8) 0.0058(8) 0.0009(8) N1 0.0124(9) 0.0133(10) 0.0189(11) 0.0003(9) 0.0061(8) -0.0007(8) N2 0.0125(9) 0.0109(10) 0.0150(10) 0.0007(8) 0.0052(7) -0.0002(7) N7 0.0150(11) 0.0138(10) 0.0167(11) -0.0018(8) 0.0039(9) -0.0010(8) C2 0.0140(10) 0.0138(12) 0.0138(11) -0.0009(10) 0.0045(9) -0.0007(11) C3 0.0122(10) 0.0126(11) 0.0087(10) -0.0007(10) -0.0011(8) 0.0000(10) C1 0.0098(10) 0.0126(10) 0.0161(11) 0.0012(9) 0.0048(8) 0.0000(9) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 O3 H5 0.85(3) . ? O3 H4 0.88(4) . ? O1 N1 1.217(3) . ? O2 N1 1.228(2) . ? N9 C3 1.328(3) . ? N9 N8 1.345(3) . ? N9 H3 0.89(3) . ? N6 C3 1.318(3) . ? N6 N7 1.362(3) . ? N5 N4 1.317(3) . ? N5 C1 1.336(3) . ? N4 N3 1.331(3) . ? N8 N7 1.299(2) . ? N3 N2 1.326(2) . ? N3 C2 1.458(3) . ? N1 C1 1.444(3) . ? N2 C1 1.316(3) . ? C2 C3 1.491(3) . ? C2 H1 0.96(2) . ? C2 H2 0.94(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H5 O3 H4 106(3) . . ? C3 N9 N8 108.47(18) . . ? C3 N9 H3 129.0(17) . . ? N8 N9 H3 122.1(17) . . ? C3 N6 N7 106.05(18) . . ? N4 N5 C1 104.61(18) . . ? N5 N4 N3 105.97(18) . . ? N7 N8 N9 106.79(19) . . ? N2 N3 N4 114.34(18) . . ? N2 N3 C2 123.54(19) . . ? N4 N3 C2 121.84(19) . . ? O1 N1 O2 125.7(2) . . ? O1 N1 C1 117.68(18) . . ? O2 N1 C1 116.61(19) . . ? C1 N2 N3 99.72(18) . . ? N8 N7 N6 109.91(19) . . ? N3 C2 C3 112.34(18) . . ? N3 C2 H1 103.9(14) . . ? C3 C2 H1 108.8(13) . . ? N3 C2 H2 107.5(14) . . ? C3 C2 H2 112.8(13) . . ? H1 C2 H2 111(2) . . ? N6 C3 N9 108.78(16) . . ? N6 C3 C2 126.2(2) . . ? N9 C3 C2 124.9(2) . . ? N2 C1 N5 115.3(2) . . ? N2 C1 N1 122.0(2) . . ? N5 C1 N1 122.6(2) . . ? 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 N5 N4 N3 -0.2(2) . . . . ? C3 N9 N8 N7 -0.2(3) . . . . ? N5 N4 N3 N2 0.1(2) . . . . ? N5 N4 N3 C2 174.25(18) . . . . ? N4 N3 N2 C1 0.1(2) . . . . ? C2 N3 N2 C1 -173.93(19) . . . . ? N9 N8 N7 N6 -0.1(3) . . . . ? C3 N6 N7 N8 0.3(3) . . . . ? N2 N3 C2 C3 -74.4(3) . . . . ? N4 N3 C2 C3 111.9(2) . . . . ? N7 N6 C3 N9 -0.4(2) . . . . ? N7 N6 C3 C2 -178.8(2) . . . . ? N8 N9 C3 N6 0.4(2) . . . . ? N8 N9 C3 C2 178.7(2) . . . . ? N3 C2 C3 N6 -55.4(3) . . . . ? N3 C2 C3 N9 126.5(2) . . . . ? N3 N2 C1 N5 -0.3(2) . . . . ? N3 N2 C1 N1 179.4(2) . . . . ? N4 N5 C1 N2 0.4(2) . . . . ? N4 N5 C1 N1 -179.32(19) . . . . ? O1 N1 C1 N2 2.4(3) . . . . ? O2 N1 C1 N2 -177.9(2) . . . . ? O1 N1 C1 N5 -177.9(2) . . . . ? O2 N1 C1 N5 1.8(3) . . . . ? 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 O3 H5 N8 0.85(3) 2.26(3) 3.008(3) 147(3) 1_465 O3 H4 O3 0.88(4) 1.93(4) 2.7961(17) 170(3) 2_545 N9 H3 N6 0.89(3) 1.92(3) 2.771(3) 159(2) 1_545 data_dx150-AGNTTz _database_code_depnum_ccdc_archive 'CCDC 704404' _audit_creation_date 2008-09-01T14:12:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C3 H2 N9 O2, C H7 N4' _chemical_formula_sum 'C4 H9 N13 O2' _chemical_formula_weight 271.24 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.027(5) _cell_length_b 30.882(4) _cell_length_c 14.223(6) _cell_angle_alpha 90 _cell_angle_beta 92.413(5) _cell_angle_gamma 90 _cell_volume 2206(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4824 _cell_measurement_theta_min 3.8828 _cell_measurement_theta_max 29.9995 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description platelets _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Oxford Xcalibur3 CCD area detector' _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_reflns_number 19929 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4316 _reflns_number_gt 2275 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0338P)^2^+0.4333P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4316 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1266 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.251 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.062 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 N7 N 0.4054(5) 0.20502(7) 1.53354(16) 0.0314(6) Uani 1 1 d . . . O4 O -0.3168(5) 0.28179(6) 1.66315(15) 0.0516(6) Uani 1 1 d . . . O3 O -0.6353(5) 0.30234(7) 1.75164(16) 0.0543(7) Uani 1 1 d . . . N10 N -0.4512(6) 0.30951(8) 1.69982(18) 0.0369(6) Uani 1 1 d . . . N16 N -0.1137(5) 0.53260(7) 1.84798(17) 0.0392(7) Uani 1 1 d . . . O2 O 0.1907(4) 0.46793(6) 1.45312(15) 0.0505(6) Uani 1 1 d . . . N11 N -0.5321(4) 0.38672(7) 1.71102(15) 0.0287(6) Uani 1 1 d . . . O1 O -0.1567(5) 0.44842(7) 1.36733(17) 0.0571(7) Uani 1 1 d . . . C3 C 0.1795(5) 0.25307(8) 1.46077(19) 0.0240(6) Uani 1 1 d . . . N17 N -0.0064(5) 0.49500(7) 1.86749(17) 0.0380(6) Uani 1 1 d . . . N25 N -0.6130(5) 0.42959(8) 1.95407(18) 0.0334(6) Uani 1 1 d . . . N22 N 0.5600(5) 0.29317(8) 1.24112(19) 0.0273(6) Uani 1 1 d . . . N9 N 0.3585(5) 0.23972(7) 1.40138(16) 0.0320(6) Uani 1 1 d . . . N2 N -0.0535(4) 0.36401(7) 1.40660(15) 0.0260(5) Uani 1 1 d . . . N4 N 0.2988(5) 0.34103(7) 1.49338(16) 0.0329(6) Uani 1 1 d . . . N13 N -0.1997(5) 0.40837(7) 1.62341(16) 0.0328(6) Uani 1 1 d . . . N26 N -0.3909(6) 0.43463(9) 2.0175(2) 0.0406(7) Uani 1 1 d . . . N20 N 0.4652(5) 0.37930(9) 1.25163(18) 0.0297(6) Uani 1 1 d . . . N5 N 0.3145(5) 0.38373(7) 1.48969(16) 0.0318(6) Uani 1 1 d . . . N21 N 0.3275(5) 0.31205(7) 1.20095(17) 0.0293(6) Uani 1 1 d . . . N24 N -0.9216(5) 0.38346(10) 1.88558(19) 0.0334(6) Uani 1 1 d . . . N14 N -0.1870(5) 0.36560(7) 1.62764(16) 0.0331(6) Uani 1 1 d . . . N23 N -0.5488(6) 0.35603(9) 1.9626(2) 0.0401(7) Uani 1 1 d . . . N12 N -0.4070(4) 0.41958(7) 1.67295(15) 0.0251(5) Uani 1 1 d . . . N19 N 0.0839(5) 0.37160(9) 1.15617(18) 0.0333(6) Uani 1 1 d . . . N3 N 0.0789(4) 0.33040(7) 1.44350(15) 0.0254(5) Uani 1 1 d . . . N1 N 0.0405(5) 0.44084(8) 1.41811(18) 0.0374(6) Uani 1 1 d . . . N8 N 0.5024(5) 0.20975(7) 1.44905(17) 0.0336(6) Uani 1 1 d . . . N6 N 0.2001(5) 0.23254(7) 1.54250(16) 0.0310(6) Uani 1 1 d . . . N18 N -0.1265(5) 0.46436(7) 1.81175(17) 0.0342(6) Uani 1 1 d . . . C7 C 0.2966(5) 0.35458(8) 1.20209(17) 0.0226(6) Uani 1 1 d . . . C6 C -0.3065(5) 0.48567(8) 1.75894(19) 0.0259(7) Uani 1 1 d . . . N15 N -0.3072(5) 0.52775(7) 1.77886(17) 0.0374(7) Uani 1 1 d . . . C5 C -0.4848(7) 0.46499(9) 1.6855(3) 0.0320(7) Uani 1 1 d . . . C1 C 0.1006(5) 0.39568(8) 1.43816(18) 0.0256(6) Uani 1 1 d . . . C8 C -0.6949(5) 0.38940(9) 1.93392(19) 0.0271(6) Uani 1 1 d . . . C2 C -0.0280(7) 0.28598(9) 1.4368(3) 0.0345(8) Uani 1 1 d . . . C4 C -0.3882(6) 0.35435(8) 1.68017(18) 0.0256(6) Uani 1 1 d . . . H4 H -0.661(6) 0.4641(8) 1.7054(19) 0.040(9) Uiso 1 1 d . . . H3 H -0.473(6) 0.4781(9) 1.627(2) 0.045(10) Uiso 1 1 d . . . H10 H 0.505(5) 0.2727(8) 1.2837(18) 0.045(7) Uiso 1 1 d . . . H6 H 0.074(5) 0.4011(9) 1.1527(18) 0.054(8) Uiso 1 1 d . . . H11 H 0.638(6) 0.2791(9) 1.196(2) 0.059(9) Uiso 1 1 d . . . H2 H -0.160(6) 0.2837(9) 1.475(2) 0.063(10) Uiso 1 1 d . . . H16 H -0.713(5) 0.4525(8) 1.9379(18) 0.051(8) Uiso 1 1 d . . . H13 H -0.618(5) 0.3303(9) 1.9545(19) 0.054(9) Uiso 1 1 d . . . H17 H -0.447(6) 0.4481(10) 2.068(2) 0.064(11) Uiso 1 1 d . . . H7 H 0.457(6) 0.4080(11) 1.250(2) 0.066(11) Uiso 1 1 d . . . H1 H -0.099(6) 0.2824(9) 1.371(2) 0.070(9) Uiso 1 1 d . . . H14 H -0.961(7) 0.3571(11) 1.869(2) 0.068(12) Uiso 1 1 d . . . H12 H -0.401(8) 0.3621(12) 1.992(3) 0.077(13) Uiso 1 1 d . . . H5 H -0.007(6) 0.3543(10) 1.120(2) 0.070(10) Uiso 1 1 d . . . H8 H 0.598(7) 0.3674(10) 1.279(2) 0.071(11) Uiso 1 1 d . . . H18 H -0.276(7) 0.4545(11) 1.991(2) 0.074(13) Uiso 1 1 d . . . H15 H -1.005(7) 0.4051(12) 1.855(2) 0.078(13) Uiso 1 1 d . . . H9 H 0.229(4) 0.2987(7) 1.1620(15) 0.077(9) 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 N7 0.0371(16) 0.0247(13) 0.0318(15) 0.0048(11) -0.0048(12) 0.0011(11) O4 0.0680(17) 0.0227(12) 0.0634(17) -0.0085(11) -0.0069(13) 0.0114(11) O3 0.0720(18) 0.0356(14) 0.0559(16) 0.0060(11) 0.0092(14) -0.0143(12) N10 0.0523(19) 0.0239(14) 0.0336(16) 0.0007(12) -0.0091(14) -0.0024(13) N16 0.0489(17) 0.0268(14) 0.0409(16) -0.0068(12) -0.0089(13) 0.0029(12) O2 0.0609(16) 0.0289(12) 0.0618(16) -0.0037(11) 0.0033(13) -0.0115(11) N11 0.0343(15) 0.0217(12) 0.0302(14) -0.0023(11) 0.0021(11) -0.0022(11) O1 0.0541(16) 0.0379(14) 0.0777(18) 0.0139(12) -0.0163(14) 0.0089(11) C3 0.0278(17) 0.0217(15) 0.0223(16) -0.0005(12) -0.0025(13) -0.0002(12) N17 0.0499(17) 0.0267(14) 0.0363(16) -0.0029(12) -0.0110(13) 0.0021(12) N25 0.0335(16) 0.0243(14) 0.0418(17) 0.0024(12) -0.0071(12) 0.0011(12) N22 0.0306(15) 0.0259(14) 0.0254(15) 0.0049(12) 0.0015(12) 0.0051(11) N9 0.0374(15) 0.0294(14) 0.0292(15) 0.0069(11) 0.0000(12) 0.0033(11) N2 0.0263(13) 0.0231(12) 0.0287(13) 0.0033(11) 0.0008(10) 0.0019(10) N4 0.0313(15) 0.0315(15) 0.0350(15) 0.0017(11) -0.0102(12) -0.0015(11) N13 0.0293(15) 0.0310(15) 0.0385(16) -0.0057(11) 0.0053(12) 0.0003(11) N26 0.0384(18) 0.0440(17) 0.0389(18) -0.0080(14) -0.0022(15) -0.0016(14) N20 0.0324(16) 0.0197(14) 0.0361(16) -0.0048(12) -0.0095(12) 0.0001(12) N5 0.0334(15) 0.0279(14) 0.0337(15) -0.0011(11) -0.0032(12) -0.0043(11) N21 0.0349(15) 0.0193(13) 0.0325(15) -0.0070(11) -0.0132(12) 0.0001(11) N24 0.0312(16) 0.0260(16) 0.0424(17) 0.0053(13) -0.0045(13) 0.0011(12) N14 0.0363(15) 0.0253(14) 0.0374(15) -0.0058(11) -0.0027(12) 0.0036(11) N23 0.0311(17) 0.0278(16) 0.061(2) 0.0065(14) -0.0039(15) 0.0035(14) N12 0.0272(14) 0.0203(12) 0.0277(14) -0.0023(10) -0.0003(11) -0.0042(10) N19 0.0352(16) 0.0247(15) 0.0389(16) -0.0061(13) -0.0125(13) 0.0026(12) N3 0.0241(14) 0.0235(12) 0.0281(14) -0.0011(10) -0.0025(11) 0.0022(10) N1 0.0418(17) 0.0250(14) 0.0456(17) 0.0045(12) 0.0048(14) 0.0002(12) N8 0.0366(15) 0.0280(13) 0.0362(16) 0.0039(12) 0.0028(12) 0.0044(11) N6 0.0386(15) 0.0269(13) 0.0272(14) 0.0044(11) 0.0000(11) 0.0058(11) N18 0.0435(16) 0.0228(13) 0.0354(15) 0.0008(11) -0.0088(12) 0.0030(11) C7 0.0271(16) 0.0224(15) 0.0184(15) -0.0032(12) 0.0028(13) -0.0010(12) C6 0.0293(17) 0.0191(15) 0.0293(17) 0.0023(12) 0.0021(13) 0.0002(12) N15 0.0425(16) 0.0228(14) 0.0460(17) -0.0054(12) -0.0098(13) 0.0069(11) C5 0.031(2) 0.0232(16) 0.042(2) -0.0029(15) -0.0034(16) 0.0005(13) C1 0.0296(17) 0.0254(15) 0.0220(16) 0.0018(12) 0.0034(13) 0.0012(13) C8 0.0240(16) 0.0262(16) 0.0315(17) 0.0070(13) 0.0044(13) 0.0008(13) C2 0.031(2) 0.0216(17) 0.050(2) 0.0013(15) -0.0071(18) -0.0015(13) C4 0.0296(17) 0.0221(15) 0.0248(16) 0.0006(12) -0.0026(13) -0.0054(12) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 N7 N8 1.324(3) . ? N7 N6 1.347(3) . ? O4 N10 1.221(3) . ? O3 N10 1.227(3) . ? N10 C4 1.450(3) . ? N16 N17 1.305(3) . ? N16 N15 1.362(3) . ? O2 N1 1.219(3) . ? N11 C4 1.320(3) . ? N11 N12 1.322(3) . ? O1 N1 1.224(3) . ? C3 N6 1.324(3) . ? C3 N9 1.325(3) . ? C3 C2 1.486(4) . ? N17 N18 1.359(3) . ? N25 C8 1.335(3) . ? N25 N26 1.414(3) . ? N25 H16 0.89(3) . ? N22 N21 1.405(3) . ? N22 H10 0.93(3) . ? N22 H11 0.88(3) . ? N9 N8 1.341(3) . ? N2 C1 1.315(3) . ? N2 N3 1.329(3) . ? N4 N5 1.322(3) . ? N4 N3 1.329(3) . ? N13 N14 1.323(3) . ? N13 N12 1.329(3) . ? N26 H17 0.89(3) . ? N26 H18 0.93(4) . ? N20 C7 1.322(3) . ? N20 H7 0.89(3) . ? N20 H8 0.84(3) . ? N5 C1 1.328(3) . ? N21 C7 1.323(3) . ? N21 H9 0.84(2) . ? N24 C8 1.319(4) . ? N24 H14 0.87(3) . ? N24 H15 0.89(4) . ? N14 C4 1.329(3) . ? N23 C8 1.320(3) . ? N23 H13 0.87(3) . ? N23 H12 0.86(4) . ? N12 C5 1.469(3) . ? N19 C7 1.337(3) . ? N19 H6 0.91(3) . ? N19 H5 0.86(3) . ? N3 C2 1.475(3) . ? N1 C1 1.453(3) . ? N18 C6 1.326(3) . ? C6 N15 1.330(3) . ? C6 C5 1.491(4) . ? C5 H4 0.94(3) . ? C5 H3 0.94(3) . ? C2 H2 0.88(3) . ? C2 H1 1.00(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 N7 N6 109.2(2) . . ? O4 N10 O3 125.1(3) . . ? O4 N10 C4 117.3(3) . . ? O3 N10 C4 117.7(3) . . ? N17 N16 N15 109.4(2) . . ? C4 N11 N12 99.7(2) . . ? N6 C3 N9 112.4(2) . . ? N6 C3 C2 123.9(3) . . ? N9 C3 C2 123.7(3) . . ? N16 N17 N18 109.0(2) . . ? C8 N25 N26 117.9(2) . . ? C8 N25 H16 121.1(18) . . ? N26 N25 H16 119.9(18) . . ? N21 N22 H10 106.5(16) . . ? N21 N22 H11 107.1(19) . . ? H10 N22 H11 107(2) . . ? C3 N9 N8 105.0(2) . . ? C1 N2 N3 99.7(2) . . ? N5 N4 N3 105.9(2) . . ? N14 N13 N12 105.9(2) . . ? N25 N26 H17 107(2) . . ? N25 N26 H18 108(2) . . ? H17 N26 H18 104(3) . . ? C7 N20 H7 122(2) . . ? C7 N20 H8 118(2) . . ? H7 N20 H8 119(3) . . ? N4 N5 C1 104.5(2) . . ? C7 N21 N22 120.2(2) . . ? C7 N21 H9 115.5(16) . . ? N22 N21 H9 121.7(16) . . ? C8 N24 H14 117(2) . . ? C8 N24 H15 122(2) . . ? H14 N24 H15 118(3) . . ? N13 N14 C4 104.5(2) . . ? C8 N23 H13 117.0(19) . . ? C8 N23 H12 116(2) . . ? H13 N23 H12 127(3) . . ? N11 N12 N13 114.5(2) . . ? N11 N12 C5 123.4(3) . . ? N13 N12 C5 122.1(2) . . ? C7 N19 H6 117.4(17) . . ? C7 N19 H5 116(2) . . ? H6 N19 H5 124(3) . . ? N2 N3 N4 114.2(2) . . ? N2 N3 C2 121.7(2) . . ? N4 N3 C2 123.8(2) . . ? O2 N1 O1 125.6(3) . . ? O2 N1 C1 117.3(3) . . ? O1 N1 C1 117.1(2) . . ? N7 N8 N9 108.9(2) . . ? C3 N6 N7 104.5(2) . . ? C6 N18 N17 105.1(2) . . ? N20 C7 N21 120.5(3) . . ? N20 C7 N19 121.0(3) . . ? N21 C7 N19 118.4(2) . . ? N18 C6 N15 111.8(2) . . ? N18 C6 C5 124.0(2) . . ? N15 C6 C5 124.1(2) . . ? C6 N15 N16 104.6(2) . . ? N12 C5 C6 109.8(2) . . ? N12 C5 H4 105.5(17) . . ? C6 C5 H4 110.3(17) . . ? N12 C5 H3 106.1(18) . . ? C6 C5 H3 112.6(18) . . ? H4 C5 H3 112(2) . . ? N2 C1 N5 115.7(2) . . ? N2 C1 N1 122.2(2) . . ? N5 C1 N1 122.1(2) . . ? N24 C8 N23 120.7(3) . . ? N24 C8 N25 119.5(3) . . ? N23 C8 N25 119.8(3) . . ? N3 C2 C3 111.8(2) . . ? N3 C2 H2 108.7(19) . . ? C3 C2 H2 110(2) . . ? N3 C2 H1 106.2(17) . . ? C3 C2 H1 111.2(17) . . ? H2 C2 H1 109(3) . . ? N11 C4 N14 115.4(2) . . ? N11 C4 N10 122.1(3) . . ? N14 C4 N10 122.4(3) . . ? 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 N15 N16 N17 N18 0.0(3) . . . . ? N6 C3 N9 N8 -1.2(3) . . . . ? C2 C3 N9 N8 -178.7(2) . . . . ? N3 N4 N5 C1 0.5(3) . . . . ? N12 N13 N14 C4 -0.3(3) . . . . ? C4 N11 N12 N13 -0.8(3) . . . . ? C4 N11 N12 C5 -179.5(2) . . . . ? N14 N13 N12 N11 0.7(3) . . . . ? N14 N13 N12 C5 179.4(2) . . . . ? C1 N2 N3 N4 -0.4(3) . . . . ? C1 N2 N3 C2 173.7(3) . . . . ? N5 N4 N3 N2 0.0(3) . . . . ? N5 N4 N3 C2 -174.0(3) . . . . ? N6 N7 N8 N9 -1.2(3) . . . . ? C3 N9 N8 N7 1.4(3) . . . . ? N9 C3 N6 N7 0.4(3) . . . . ? C2 C3 N6 N7 178.0(2) . . . . ? N8 N7 N6 C3 0.5(3) . . . . ? N16 N17 N18 C6 0.3(3) . . . . ? N22 N21 C7 N20 -9.2(4) . . . . ? N22 N21 C7 N19 174.3(3) . . . . ? N17 N18 C6 N15 -0.4(3) . . . . ? N17 N18 C6 C5 179.0(3) . . . . ? N18 C6 N15 N16 0.4(3) . . . . ? C5 C6 N15 N16 -179.1(3) . . . . ? N17 N16 N15 C6 -0.2(3) . . . . ? N11 N12 C5 C6 100.1(3) . . . . ? N13 N12 C5 C6 -78.5(3) . . . . ? N18 C6 C5 N12 -7.2(4) . . . . ? N15 C6 C5 N12 172.2(3) . . . . ? N3 N2 C1 N5 0.7(3) . . . . ? N3 N2 C1 N1 -179.2(2) . . . . ? N4 N5 C1 N2 -0.8(3) . . . . ? N4 N5 C1 N1 179.1(2) . . . . ? O2 N1 C1 N2 177.6(3) . . . . ? O1 N1 C1 N2 -2.5(4) . . . . ? O2 N1 C1 N5 -2.3(4) . . . . ? O1 N1 C1 N5 177.6(3) . . . . ? N26 N25 C8 N24 170.8(3) . . . . ? N26 N25 C8 N23 -9.2(4) . . . . ? N2 N3 C2 C3 165.5(3) . . . . ? N4 N3 C2 C3 -21.0(4) . . . . ? N6 C3 C2 N3 102.5(3) . . . . ? N9 C3 C2 N3 -80.3(4) . . . . ? N12 N11 C4 N14 0.6(3) . . . . ? N12 N11 C4 N10 -177.5(2) . . . . ? N13 N14 C4 N11 -0.2(3) . . . . ? N13 N14 C4 N10 177.9(2) . . . . ? O4 N10 C4 N11 175.4(2) . . . . ? O3 N10 C4 N11 -4.4(4) . . . . ? O4 N10 C4 N14 -2.6(4) . . . . ? O3 N10 C4 N14 177.6(2) . . . . ? 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 N21 H9 N7 0.84(2) 2.40(2) 3.166(4) 153(2) 4_565 N21 H9 O4 0.84(2) 2.50(2) 3.030(3) 122.5(18) 4_665 N22 H10 N9 0.93(3) 2.12(3) 3.023(4) 166(2) . N19 H6 N16 0.91(3) 2.06(3) 2.963(4) 171(2) 3_568 N22 H11 N6 0.88(3) 2.24(3) 3.045(4) 151(2) 4_665 N25 H16 N17 0.89(3) 2.19(3) 3.050(4) 163(2) 1_455 N23 H13 N8 0.87(3) 2.27(3) 3.036(4) 146(2) 4_466 N26 H17 N16 0.89(3) 2.62(3) 3.359(5) 141(3) 3_469 N20 H7 N15 0.89(3) 2.16(4) 3.005(4) 160(3) 3_568 N24 H14 N8 0.87(3) 2.37(3) 3.046(4) 135(3) 4_466 N19 H5 N7 0.86(3) 2.24(3) 3.052(4) 158(3) 4_565 N20 H8 N2 0.84(3) 2.48(3) 3.238(4) 151(3) 1_655 N26 H18 N17 0.93(4) 2.59(4) 3.480(4) 160(3) . N24 H15 N18 0.89(4) 2.02(4) 2.883(4) 163(3) 1_455 data_dx132-NH4NTTz_H2O _database_code_depnum_ccdc_archive 'CCDC 704406' _audit_creation_date 2008-09-01T12:15:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C3 H2 N9 O2, H4 N, H2 O' _chemical_formula_sum 'C3 H8 N10 O3' _chemical_formula_weight 232.19 #------------------ UNIT CELL INFORMATION -----------------------------------# _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 7.4710(4) _cell_length_b 7.8386(5) _cell_length_c 18.0365(11) _cell_angle_alpha 84.318(5) _cell_angle_beta 78.597(5) _cell_angle_gamma 69.203(6) _cell_volume 967.47(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3739 _cell_measurement_theta_min 4.0479 _cell_measurement_theta_max 32.6298 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Oxford Xcalibur3 CCD area detector' _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_reflns_number 9896 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.06 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_full 26.00 _reflns_number_total 3802 _reflns_number_gt 2441 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0338P)^2^+0.4333P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3802 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0797 _refine_ls_wR_factor_gt 0.0719 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.149 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.038 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 O5 O 0.75109(18) 0.78544(16) 0.50961(7) 0.0384(3) Uani 1 1 d . . . O6 O 0.07706(18) 0.48721(16) -0.11288(7) 0.0375(3) Uani 1 1 d . . . N21 N 0.1493(2) 1.2011(2) -0.00375(9) 0.0295(3) Uani 1 1 d . . . N19 N 0.6585(3) 1.1404(2) 0.43945(10) 0.0353(4) Uani 1 1 d . . . H2 H 1.209(2) 0.081(2) 0.2896(8) 0.025(4) Uiso 1 1 d . . . H4 H 0.647(2) 0.306(2) -0.1196(9) 0.036(4) Uiso 1 1 d . . . H1 H 1.206(2) 0.202(2) 0.2111(9) 0.034(4) Uiso 1 1 d . . . H3 H 0.804(2) 0.412(2) -0.1370(8) 0.036(5) Uiso 1 1 d . . . H8 H 0.188(3) 1.247(3) 0.0360(12) 0.069(7) Uiso 1 1 d . . . H7 H 0.132(3) 1.287(3) -0.0478(11) 0.053(5) Uiso 1 1 d . . . H6 H 0.034(3) 1.184(2) 0.0115(10) 0.050(6) Uiso 1 1 d . . . H5 H 0.246(3) 1.087(3) -0.0183(11) 0.062(6) Uiso 1 1 d . . . H11 H 0.509(4) 1.183(3) 0.4528(13) 0.095(8) Uiso 1 1 d . . . H13 H 0.701(3) 1.216(3) 0.4596(14) 0.087(8) Uiso 1 1 d . . . H15 H 0.805(3) 0.691(3) 0.4773(12) 0.072(7) Uiso 1 1 d . . . H16 H 0.822(3) 0.750(3) 0.5469(12) 0.069(7) Uiso 1 1 d . . . H9 H 0.173(3) 0.521(3) -0.1018(11) 0.067(7) Uiso 1 1 d . . . H14 H 0.691(3) 1.137(3) 0.3906(13) 0.063(7) Uiso 1 1 d . . . H10 H 0.098(3) 0.479(3) -0.1626(14) 0.078(8) Uiso 1 1 d . . . H12 H 0.708(3) 1.019(4) 0.4583(13) 0.087(8) Uiso 1 1 d . . . N11 N 0.74083(18) 0.31285(17) -0.26687(7) 0.0302(3) Uani 1 1 d . . . N12 N 0.64795(18) 0.44399(17) -0.21801(7) 0.0265(3) Uani 1 1 d . . . N3 N 1.00151(18) 0.09348(16) 0.23160(7) 0.0264(3) Uani 1 1 d . . . N15 N 0.34707(18) 0.60274(18) -0.06892(7) 0.0314(3) Uani 1 1 d . . . N16 N 0.27426(19) 0.76189(18) -0.03368(7) 0.0330(3) Uani 1 1 d . . . N2 N 0.84791(18) 0.07060(16) 0.27590(7) 0.0279(3) Uani 1 1 d . . . O1 O 0.52769(16) -0.02023(16) 0.31592(7) 0.0456(3) Uani 1 1 d . . . C3 C 1.0173(2) 0.3394(2) 0.30116(8) 0.0267(4) Uani 1 1 d . . . N18 N 0.57845(18) 0.72078(18) -0.07788(7) 0.0326(3) Uani 1 1 d . . . N14 N 0.5512(2) 0.56550(19) -0.31956(7) 0.0413(4) Uani 1 1 d . . . N9 N 0.9174(2) 0.49683(18) 0.27076(8) 0.0402(4) Uani 1 1 d . . . C5 C 0.6702(3) 0.4212(2) -0.13762(9) 0.0311(4) Uani 1 1 d . . . O3 O 0.8429(2) 0.14866(18) -0.40231(7) 0.0557(4) Uani 1 1 d . . . C2 C 1.1288(2) 0.1724(2) 0.25735(10) 0.0299(4) Uani 1 1 d . . . N7 N 0.8999(2) 0.52657(19) 0.39021(8) 0.0376(4) Uani 1 1 d . . . N5 N 0.9044(2) -0.04498(18) 0.16179(8) 0.0353(3) Uani 1 1 d . . . N13 N 0.5343(2) 0.59641(19) -0.24760(8) 0.0394(4) Uani 1 1 d . . . N4 N 1.0397(2) 0.02623(17) 0.16341(7) 0.0342(3) Uani 1 1 d . . . N6 N 1.0111(2) 0.35132(18) 0.37480(7) 0.0367(4) Uani 1 1 d . . . N1 N 0.6211(2) -0.06322(19) 0.25266(9) 0.0386(4) Uani 1 1 d . . . C6 C 0.5325(2) 0.5825(2) -0.09482(8) 0.0255(4) Uani 1 1 d . . . C1 C 0.7938(2) -0.0147(2) 0.22998(9) 0.0284(4) Uani 1 1 d . . . N8 N 0.8436(2) 0.61255(18) 0.32835(8) 0.0424(4) Uani 1 1 d . . . N10 N 0.7325(2) 0.3063(2) -0.39965(8) 0.0426(4) Uani 1 1 d . . . N17 N 0.4123(2) 0.83180(18) -0.03891(7) 0.0354(3) Uani 1 1 d . . . O2 O 0.58070(18) -0.14181(18) 0.20659(8) 0.0571(4) Uani 1 1 d . . . O4 O 0.6636(2) 0.39769(18) -0.45314(7) 0.0656(4) Uani 1 1 d . . . C4 C 0.6751(2) 0.3956(2) -0.32793(8) 0.0304(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.0424(7) 0.0337(7) 0.0330(7) -0.0037(6) -0.0098(6) -0.0031(6) O6 0.0405(8) 0.0456(8) 0.0316(8) -0.0012(6) -0.0096(6) -0.0192(6) N21 0.0283(9) 0.0289(9) 0.0310(9) -0.0049(7) -0.0057(7) -0.0082(7) N19 0.0429(10) 0.0358(10) 0.0265(9) -0.0010(7) -0.0056(7) -0.0131(8) N11 0.0357(8) 0.0276(7) 0.0249(7) -0.0054(6) -0.0018(6) -0.0087(6) N12 0.0276(7) 0.0249(7) 0.0250(7) -0.0015(6) -0.0046(6) -0.0065(6) N3 0.0272(7) 0.0250(7) 0.0248(7) -0.0012(5) -0.0033(6) -0.0068(6) N15 0.0289(8) 0.0352(8) 0.0298(8) -0.0030(6) -0.0044(6) -0.0108(7) N16 0.0295(8) 0.0375(8) 0.0290(8) -0.0040(6) -0.0038(6) -0.0079(7) N2 0.0257(7) 0.0257(7) 0.0301(8) -0.0022(6) -0.0049(6) -0.0056(6) O1 0.0284(7) 0.0476(8) 0.0560(9) -0.0064(6) -0.0018(6) -0.0090(6) C3 0.0271(9) 0.0288(9) 0.0249(9) -0.0008(7) -0.0048(7) -0.0105(7) N18 0.0278(8) 0.0312(8) 0.0375(8) -0.0080(6) -0.0051(6) -0.0069(7) N14 0.0581(10) 0.0357(9) 0.0242(8) -0.0006(6) -0.0098(7) -0.0078(8) N9 0.0549(10) 0.0302(8) 0.0310(8) -0.0004(6) -0.0122(7) -0.0069(8) C5 0.0345(10) 0.0315(10) 0.0250(9) -0.0009(7) -0.0089(7) -0.0065(8) O3 0.0758(10) 0.0419(8) 0.0403(8) -0.0154(6) 0.0017(7) -0.0118(8) C2 0.0269(9) 0.0330(10) 0.0310(10) -0.0030(8) -0.0036(8) -0.0120(8) N7 0.0446(9) 0.0333(8) 0.0313(9) -0.0058(6) -0.0049(7) -0.0087(7) N5 0.0423(9) 0.0314(8) 0.0332(9) -0.0033(6) -0.0121(7) -0.0103(7) N13 0.0479(9) 0.0322(8) 0.0292(8) -0.0004(6) -0.0115(7) -0.0006(7) N4 0.0446(9) 0.0305(8) 0.0256(8) -0.0034(6) -0.0066(6) -0.0098(7) N6 0.0445(9) 0.0313(8) 0.0283(8) -0.0018(6) -0.0082(6) -0.0044(7) N1 0.0274(8) 0.0317(8) 0.0571(11) -0.0047(7) -0.0155(8) -0.0054(7) C6 0.0294(9) 0.0268(9) 0.0199(8) -0.0002(6) -0.0085(7) -0.0071(7) C1 0.0242(9) 0.0231(8) 0.0364(10) -0.0017(7) -0.0110(7) -0.0032(7) N8 0.0569(10) 0.0298(8) 0.0364(9) -0.0030(7) -0.0122(7) -0.0075(7) N10 0.0648(11) 0.0396(10) 0.0268(9) -0.0028(7) -0.0021(7) -0.0248(9) N17 0.0324(8) 0.0339(8) 0.0378(9) -0.0089(6) -0.0063(6) -0.0070(7) O2 0.0466(8) 0.0586(9) 0.0777(10) -0.0194(7) -0.0212(7) -0.0222(7) O4 0.1202(13) 0.0525(9) 0.0273(7) 0.0017(6) -0.0206(8) -0.0302(9) C4 0.0407(10) 0.0290(9) 0.0226(9) -0.0014(7) -0.0026(7) -0.0147(8) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 O5 H15 0.91(2) . ? O5 H16 0.90(2) . ? O6 H9 0.91(2) . ? O6 H10 0.88(2) . ? N21 H8 0.96(2) . ? N21 H7 0.99(2) . ? N21 H6 0.91(2) . ? N21 H5 0.95(2) . ? N19 H11 1.03(3) . ? N19 H13 0.89(3) . ? N19 H14 0.87(2) . ? N19 H12 0.95(3) . ? N11 C4 1.3117(19) . ? N11 N12 1.3214(17) . ? N12 N13 1.3289(17) . ? N12 C5 1.478(2) . ? N3 N2 1.3201(17) . ? N3 N4 1.3247(17) . ? N3 C2 1.467(2) . ? N15 C6 1.3284(19) . ? N15 N16 1.3396(17) . ? N16 N17 1.3134(17) . ? N2 C1 1.3155(19) . ? O1 N1 1.2234(18) . ? C3 N9 1.3242(19) . ? C3 N6 1.3312(19) . ? C3 C2 1.484(2) . ? N18 C6 1.3257(19) . ? N18 N17 1.3421(17) . ? N14 N13 1.3173(18) . ? N14 C4 1.328(2) . ? N9 N8 1.3457(18) . ? C5 C6 1.486(2) . ? C5 H4 0.987(17) . ? C5 H3 0.976(16) . ? O3 N10 1.2174(18) . ? C2 H2 0.979(15) . ? C2 H1 0.974(17) . ? N7 N8 1.3080(18) . ? N7 N6 1.3523(18) . ? N5 N4 1.3232(18) . ? N5 C1 1.330(2) . ? N1 O2 1.2222(17) . ? N1 C1 1.444(2) . ? N10 O4 1.2275(19) . ? N10 C4 1.447(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H15 O5 H16 103.7(18) . . ? H9 O6 H10 106.8(19) . . ? H8 N21 H7 112.0(16) . . ? H8 N21 H6 112.1(17) . . ? H7 N21 H6 105.7(15) . . ? H8 N21 H5 108.1(16) . . ? H7 N21 H5 110.3(16) . . ? H6 N21 H5 108.6(16) . . ? H11 N19 H13 109(2) . . ? H11 N19 H14 107.9(18) . . ? H13 N19 H14 113(2) . . ? H11 N19 H12 107.9(19) . . ? H13 N19 H12 112(2) . . ? H14 N19 H12 106.6(18) . . ? C4 N11 N12 99.70(12) . . ? N11 N12 N13 114.13(12) . . ? N11 N12 C5 122.38(12) . . ? N13 N12 C5 123.49(12) . . ? N2 N3 N4 114.13(12) . . ? N2 N3 C2 123.12(12) . . ? N4 N3 C2 122.56(13) . . ? C6 N15 N16 104.56(12) . . ? N17 N16 N15 109.12(12) . . ? C1 N2 N3 100.15(12) . . ? N9 C3 N6 111.90(13) . . ? N9 C3 C2 123.73(14) . . ? N6 C3 C2 124.33(14) . . ? C6 N18 N17 104.13(12) . . ? N13 N14 C4 104.21(12) . . ? C3 N9 N8 105.07(13) . . ? N12 C5 C6 110.26(13) . . ? N12 C5 H4 105.4(9) . . ? C6 C5 H4 113.3(9) . . ? N12 C5 H3 106.2(9) . . ? C6 C5 H3 109.6(9) . . ? H4 C5 H3 111.7(13) . . ? N3 C2 C3 112.25(13) . . ? N3 C2 H2 108.6(8) . . ? C3 C2 H2 108.8(9) . . ? N3 C2 H1 104.7(9) . . ? C3 C2 H1 110.2(9) . . ? H2 C2 H1 112.2(12) . . ? N8 N7 N6 109.42(12) . . ? N4 N5 C1 104.34(12) . . ? N14 N13 N12 106.14(12) . . ? N5 N4 N3 106.16(12) . . ? C3 N6 N7 104.41(12) . . ? O2 N1 O1 126.01(15) . . ? O2 N1 C1 116.98(15) . . ? O1 N1 C1 117.01(14) . . ? N18 C6 N15 112.43(13) . . ? N18 C6 C5 124.72(15) . . ? N15 C6 C5 122.85(14) . . ? N2 C1 N5 115.22(14) . . ? N2 C1 N1 121.08(14) . . ? N5 C1 N1 123.66(14) . . ? N7 N8 N9 109.19(13) . . ? O3 N10 O4 125.40(15) . . ? O3 N10 C4 118.26(14) . . ? O4 N10 C4 116.34(15) . . ? N16 N17 N18 109.76(12) . . ? N11 C4 N14 115.81(14) . . ? N11 C4 N10 122.02(15) . . ? N14 C4 N10 122.16(14) . . ? 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 C4 N11 N12 N13 -0.31(17) . . . . ? C4 N11 N12 C5 179.77(14) . . . . ? C6 N15 N16 N17 0.02(15) . . . . ? N4 N3 N2 C1 -0.30(15) . . . . ? C2 N3 N2 C1 -175.39(13) . . . . ? N6 C3 N9 N8 -0.57(18) . . . . ? C2 C3 N9 N8 -178.31(14) . . . . ? N11 N12 C5 C6 -173.72(13) . . . . ? N13 N12 C5 C6 6.4(2) . . . . ? N2 N3 C2 C3 -46.0(2) . . . . ? N4 N3 C2 C3 139.37(14) . . . . ? N9 C3 C2 N3 -70.2(2) . . . . ? N6 C3 C2 N3 112.29(17) . . . . ? C4 N14 N13 N12 -0.17(17) . . . . ? N11 N12 N13 N14 0.32(18) . . . . ? C5 N12 N13 N14 -179.76(14) . . . . ? C1 N5 N4 N3 0.01(15) . . . . ? N2 N3 N4 N5 0.20(16) . . . . ? C2 N3 N4 N5 175.31(13) . . . . ? N9 C3 N6 N7 0.29(18) . . . . ? C2 C3 N6 N7 178.02(14) . . . . ? N8 N7 N6 C3 0.12(17) . . . . ? N17 N18 C6 N15 0.42(16) . . . . ? N17 N18 C6 C5 -179.36(13) . . . . ? N16 N15 C6 N18 -0.28(16) . . . . ? N16 N15 C6 C5 179.50(13) . . . . ? N12 C5 C6 N18 -98.42(18) . . . . ? N12 C5 C6 N15 81.83(19) . . . . ? N3 N2 C1 N5 0.31(17) . . . . ? N3 N2 C1 N1 -177.22(13) . . . . ? N4 N5 C1 N2 -0.21(17) . . . . ? N4 N5 C1 N1 177.25(13) . . . . ? O2 N1 C1 N2 179.81(14) . . . . ? O1 N1 C1 N2 0.5(2) . . . . ? O2 N1 C1 N5 2.5(2) . . . . ? O1 N1 C1 N5 -176.77(15) . . . . ? N6 N7 N8 N9 -0.48(18) . . . . ? C3 N9 N8 N7 0.63(18) . . . . ? N15 N16 N17 N18 0.23(16) . . . . ? C6 N18 N17 N16 -0.39(16) . . . . ? N12 N11 C4 N14 0.20(18) . . . . ? N12 N11 C4 N10 -179.06(14) . . . . ? N13 N14 C4 N11 -0.02(19) . . . . ? N13 N14 C4 N10 179.23(14) . . . . ? O3 N10 C4 N11 1.1(2) . . . . ? O4 N10 C4 N11 -179.18(15) . . . . ? O3 N10 C4 N14 -178.12(15) . . . . ? O4 N10 C4 N14 1.6(2) . . . . ? 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 N21 H8 N18 0.96(2) 2.14(2) 2.987(2) 146.5(16) 2_675 N21 H8 O6 0.96(2) 2.60(2) 3.151(2) 116.8(14) 2_575 N21 H7 O6 0.99(2) 1.84(2) 2.8076(19) 166.6(16) 1_565 N21 H6 N16 0.91(2) 2.15(2) 3.016(2) 160.4(16) 2_575 N21 H5 N17 0.95(2) 1.97(2) 2.911(2) 169.7(17) . N21 H5 N16 0.95(2) 2.52(2) 3.302(2) 139.4(15) . N19 H11 O5 1.03(3) 1.86(3) 2.877(2) 167(2) 2_676 N19 H13 O4 0.89(3) 2.14(3) 2.946(2) 150(2) 1_566 O5 H15 N7 0.91(2) 1.99(2) 2.8824(19) 167.7(19) . O5 H16 N6 0.90(2) 1.99(2) 2.8847(18) 174.6(19) 2_766 O6 H9 N15 0.91(2) 1.85(2) 2.7550(18) 173.1(19) . N19 H14 N2 0.87(2) 2.18(2) 3.020(2) 163.6(18) 1_565 N19 H14 O1 0.87(2) 2.62(2) 3.130(2) 118.8(16) 1_565 O6 H10 N9 0.88(2) 1.96(2) 2.8307(19) 167(2) 2_665 N19 H12 O5 0.95(3) 1.91(3) 2.847(2) 167(2) .