# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'T M Klapotke' _publ_contact_author_email TMK@CUP.UNI-MUENCHEN.DE _publ_section_title ; Azidoformamidinium and 5-Aminotetrazolium Dinitramide - Two Highly Energetic Isomers with a Balanced Oxygen Content ; loop_ _publ_author_name 'T M Klapotke' 'Jorg Stierstorfer' # Attachment 'cx343a_AFDN.cif' data_cx343 _database_code_depnum_ccdc_archive 'CCDC 674701' _audit_update_record 19.10.2007 _chemical_name_systematic 'azidoformamidinium dinitramide monohydrate' _chemical_compound_source ? _chemical_name_common 'azidoformamidinium dinitramide monohydrate' _chemical_formula_moiety 'C H4 N5, N3 O4, H2 O' _chemical_formula_sum 'C H6 N8 O5' _chemical_formula_weight 210.14 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 4540 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 28.00 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 1051 _reflns_number_gt 703 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0503858756 _diffrn_orient_matrix_UB_12 -0.0160434639 _diffrn_orient_matrix_UB_13 -0.0888142153 _diffrn_orient_matrix_UB_21 0.0321773413 _diffrn_orient_matrix_UB_22 0.0349948956 _diffrn_orient_matrix_UB_23 -0.0342644021 _diffrn_orient_matrix_UB_31 0.0773140057 _diffrn_orient_matrix_UB_32 -0.0031794607 _diffrn_orient_matrix_UB_33 0.0722863054 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_Int_Tables_number 11 _symmetry_space_group_name_Hall '-P 2yb' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 7.2806(8) _cell_length_b 5.9376(7) _cell_length_c 9.8324(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.609(7) _cell_angle_gamma 90.00 _cell_volume 397.85(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2020 _cell_measurement_theta_min 4.0636 _cell_measurement_theta_max 32.5724 _cell_special_details ? _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97273 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.309 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.067 _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 SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _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_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1051 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.923 _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 N4 N 0.5752(3) 0.2500 0.2780(2) 0.0238(4) Uani 1 2 d S . . N5 N 0.7592(3) 0.2500 0.1276(2) 0.0222(4) Uani 1 2 d S . . N6 N 0.4329(2) 0.2500 0.02042(18) 0.0226(4) Uani 1 2 d S . . N7 N 0.2640(2) 0.2500 0.02830(16) 0.0217(4) Uani 1 2 d S . . N8 N 0.1056(2) 0.2500 0.01283(18) 0.0304(5) Uani 1 2 d S . . C1 C 0.5927(3) 0.2500 0.1493(2) 0.0187(4) Uani 1 2 d S . . O1 O -0.1341(2) 0.2500 0.60177(15) 0.0278(4) Uani 1 2 d S . . O2 O 0.1817(2) 0.2500 0.71008(15) 0.0310(4) Uani 1 2 d S . . O3 O 0.19141(19) 0.2500 0.31178(14) 0.0276(4) Uani 1 2 d S . . O4 O 0.3726(2) 0.2500 0.53759(16) 0.0400(4) Uani 1 2 d S . . N1 N 0.0331(2) 0.2500 0.45958(16) 0.0211(4) Uani 1 2 d S . . N2 N 0.0362(2) 0.2500 0.60021(17) 0.0206(4) Uani 1 2 d S . . N3 N 0.2126(2) 0.2500 0.44327(18) 0.0225(4) Uani 1 2 d S . . O5 O 0.6758(3) 0.2500 -0.17597(17) 0.0339(4) Uani 1 2 d S . . H51 H 0.560(4) 0.2500 -0.221(3) 0.027(6) Uiso 1 2 d S . . H52 H 0.749(4) 0.2500 -0.234(3) 0.058(9) Uiso 1 2 d S . . H5A H 0.861(4) 0.2500 0.196(3) 0.031(7) Uiso 1 2 d S . . H4A H 0.669(3) 0.2500 0.346(3) 0.015(5) Uiso 1 2 d S . . H4B H 0.466(4) 0.2500 0.281(3) 0.035(7) Uiso 1 2 d S . . H5B H 0.749(3) 0.2500 0.042(3) 0.031(7) Uiso 1 2 d S . . 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 N4 0.0158(9) 0.0375(11) 0.0174(9) 0.000 0.0049(8) 0.000 N5 0.0162(9) 0.0331(10) 0.0166(9) 0.000 0.0050(7) 0.000 N6 0.0152(8) 0.0340(10) 0.0187(8) 0.000 0.0063(6) 0.000 N7 0.0211(9) 0.0297(9) 0.0149(8) 0.000 0.0072(7) 0.000 N8 0.0208(10) 0.0518(12) 0.0197(9) 0.000 0.0084(8) 0.000 C1 0.0188(10) 0.0174(9) 0.0195(10) 0.000 0.0060(8) 0.000 O1 0.0254(8) 0.0361(8) 0.0281(8) 0.000 0.0171(6) 0.000 O2 0.0312(8) 0.0458(9) 0.0148(7) 0.000 0.0065(6) 0.000 O3 0.0257(8) 0.0439(9) 0.0171(7) 0.000 0.0125(6) 0.000 O4 0.0180(8) 0.0768(12) 0.0227(8) 0.000 0.0041(7) 0.000 N1 0.0178(8) 0.0316(9) 0.0152(8) 0.000 0.0075(7) 0.000 N2 0.0245(9) 0.0208(8) 0.0187(9) 0.000 0.0102(7) 0.000 N3 0.0197(9) 0.0288(9) 0.0204(9) 0.000 0.0087(7) 0.000 O5 0.0210(9) 0.0606(11) 0.0206(8) 0.000 0.0081(7) 0.000 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 N4 C1 1.315(3) . ? N4 H4A 0.77(2) . ? N4 H4B 0.81(3) . ? N5 C1 1.303(3) . ? N5 H5A 0.81(3) . ? N5 H5B 0.82(2) . ? N6 N7 1.259(2) . ? N6 C1 1.386(3) . ? N7 N8 1.109(2) . ? O1 N2 1.246(2) . ? O2 N2 1.218(2) . ? O3 N3 1.247(2) . ? O4 N3 1.207(2) . ? N1 N3 1.372(2) . ? N1 N2 1.375(2) . ? O5 H51 0.80(3) . ? O5 H52 0.91(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 C1 N4 H4A 118.6(15) . . ? C1 N4 H4B 118.1(19) . . ? H4A N4 H4B 123(3) . . ? C1 N5 H5A 119.7(17) . . ? C1 N5 H5B 114.6(16) . . ? H5A N5 H5B 126(2) . . ? N7 N6 C1 117.85(16) . . ? N8 N7 N6 169.33(18) . . ? N5 C1 N4 124.65(19) . . ? N5 C1 N6 112.31(18) . . ? N4 C1 N6 123.04(18) . . ? N3 N1 N2 115.99(14) . . ? O2 N2 O1 123.23(16) . . ? O2 N2 N1 126.41(16) . . ? O1 N2 N1 110.37(15) . . ? O4 N3 O3 122.06(17) . . ? O4 N3 N1 127.72(16) . . ? O3 N3 N1 110.22(15) . . ? H51 O5 H52 113(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 C1 N6 N7 N8 180.0 . . . . ? N7 N6 C1 N5 180.0 . . . . ? N7 N6 C1 N4 0.0 . . . . ? N3 N1 N2 O2 0.0 . . . . ? N3 N1 N2 O1 180.0 . . . . ? N2 N1 N3 O4 0.0 . . . . ? N2 N1 N3 O3 180.0 . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 O5 H51 O4 0.80(3) 2.29(2) 2.903(2) 135(2) 1_554 O5 H51 O2 0.80(3) 2.60(3) 3.370(2) 163(2) 1_554 O5 H52 O1 0.91(3) 2.07(3) 2.970(2) 169(3) 1_654 N5 H5A O3 0.81(3) 2.27(3) 3.028(2) 156(2) 1_655 N5 H5A N1 0.81(3) 2.45(3) 3.170(3) 149(2) 1_655 N4 H4A O1 0.77(2) 2.42(2) 3.142(2) 157(2) 1_655 N4 H4A N1 0.77(2) 2.49(2) 3.180(3) 150(2) 1_655 N4 H4B O3 0.81(3) 2.12(3) 2.927(3) 175(3) . N5 H5B O5 0.82(2) 2.02(3) 2.829(3) 171(2) . _geom_special_details ? # Attachment 'dx071_ATDN.cif' data_dx071 _database_code_depnum_ccdc_archive 'CCDC 680293' _audit_update_record ? _chemical_name_systematic '5-aminotetrazolium dinitramide' _chemical_compound_source ? _chemical_name_common '5-aminotetrazolium dinitramide' _chemical_formula_moiety 'C H4 N5, N3 O4' _chemical_formula_sum 'C H4 N8 O4' _chemical_formula_weight 192.12 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 2691 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.31 _diffrn_reflns_theta_max 33.42 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 33.42 _diffrn_measured_fraction_theta_full 0.918 _reflns_number_total 1236 _reflns_number_gt 848 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0015054239 _diffrn_orient_matrix_UB_12 0.0302007982 _diffrn_orient_matrix_UB_13 0.0827155083 _diffrn_orient_matrix_UB_21 0.1481540038 _diffrn_orient_matrix_UB_22 -0.0178531585 _diffrn_orient_matrix_UB_23 0.0109327959 _diffrn_orient_matrix_UB_31 0.0393865855 _diffrn_orient_matrix_UB_32 0.0663702035 _diffrn_orient_matrix_UB_33 -0.0346249850 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P c' _symmetry_Int_Tables_number ? _symmetry_space_group_name_Hall 'P -2yc' 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 4.6283(3) _cell_length_b 9.4580(6) _cell_length_c 9.0071(5) _cell_angle_alpha 90.00 _cell_angle_beta 119.343(4) _cell_angle_gamma 90.00 _cell_volume 343.70(4) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1152 _cell_measurement_theta_min 4.3054 _cell_measurement_theta_max 33.3169 _cell_special_details ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.856 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90343 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.153 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.050 _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 SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 1236 _refine_ls_number_parameters 134 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0638 _refine_ls_wR_factor_gt 0.0603 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.863 _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 N1 N -0.2408(4) -0.86405(18) -0.0577(2) 0.0259(4) Uani 1 1 d . . . N2 N -0.3768(5) -0.96386(19) -0.0018(2) 0.0308(4) Uani 1 1 d . . . N3 N -0.2719(5) -0.94112(19) 0.1550(2) 0.0327(4) Uani 1 1 d . . . N4 N -0.0674(4) -0.8265(2) 0.2013(2) 0.0295(4) Uani 1 1 d . . . N5 N 0.1194(5) -0.6662(2) 0.0639(2) 0.0316(4) Uani 1 1 d . . . C1 C -0.0489(5) -0.7758(2) 0.0683(2) 0.0217(4) Uani 1 1 d . . . O1 O 0.0533(3) -0.76711(16) 0.74690(16) 0.0310(3) Uani 1 1 d . . . O2 O 0.2081(3) -0.81330(16) 0.56110(18) 0.0308(3) Uani 1 1 d . . . O3 O -0.3178(4) -0.55338(18) 0.66825(17) 0.0378(4) Uani 1 1 d . . . O4 O -0.6460(4) -0.53924(18) 0.39691(19) 0.0363(4) Uani 1 1 d . . . N8 N -0.3973(4) -0.58741(18) 0.5228(2) 0.0249(4) Uani 1 1 d . . . N6 N 0.0206(4) -0.75182(18) 0.60420(19) 0.0223(3) Uani 1 1 d . . . N7 N -0.2188(4) -0.67611(19) 0.4753(2) 0.0257(4) Uani 1 1 d . . . H1 H -0.268(8) -0.864(3) -0.161(4) 0.057(9) Uiso 1 1 d . . . H4 H 0.031(7) -0.801(3) 0.301(4) 0.049(8) Uiso 1 1 d . . . H5B H 0.098(6) -0.641(3) -0.038(4) 0.038(7) Uiso 1 1 d . . . H5A H 0.244(7) -0.617(3) 0.162(4) 0.045(7) 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 N1 0.0325(9) 0.0277(9) 0.0174(8) -0.0012(7) 0.0122(7) -0.0064(7) N2 0.0384(10) 0.0291(9) 0.0255(9) 0.0013(8) 0.0161(8) -0.0070(8) N3 0.0425(11) 0.0311(10) 0.0271(9) 0.0016(7) 0.0191(8) -0.0075(8) N4 0.0400(10) 0.0334(10) 0.0164(9) -0.0022(7) 0.0149(8) -0.0080(8) N5 0.0402(11) 0.0317(10) 0.0251(9) -0.0065(8) 0.0177(9) -0.0122(8) C1 0.0255(10) 0.0238(10) 0.0165(9) 0.0004(7) 0.0109(8) 0.0012(8) O1 0.0387(9) 0.0368(8) 0.0188(7) 0.0039(6) 0.0153(6) 0.0043(7) O2 0.0331(8) 0.0366(8) 0.0274(7) 0.0009(6) 0.0185(6) 0.0098(6) O3 0.0366(8) 0.0481(9) 0.0221(7) -0.0119(7) 0.0092(6) 0.0106(7) O4 0.0331(8) 0.0460(10) 0.0231(7) 0.0004(7) 0.0085(6) 0.0156(7) N8 0.0244(8) 0.0298(9) 0.0197(8) -0.0044(7) 0.0103(7) 0.0009(7) N6 0.0241(8) 0.0246(8) 0.0201(8) -0.0021(6) 0.0124(6) -0.0019(6) N7 0.0296(8) 0.0296(9) 0.0181(7) 0.0012(7) 0.0118(7) 0.0079(7) 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 N1 C1 1.336(2) . ? N1 N2 1.360(2) . ? N1 H1 0.87(3) . ? N2 N3 1.267(2) . ? N3 N4 1.363(3) . ? N4 C1 1.331(2) . ? N4 H4 0.82(3) . ? N5 C1 1.308(3) . ? N5 H5B 0.90(3) . ? N5 H5A 0.91(3) . ? O1 N6 1.2269(19) . ? O2 N6 1.254(2) . ? O3 N8 1.218(2) . ? O4 N8 1.241(2) . ? N8 N7 1.384(2) . ? N6 N7 1.352(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 C1 N1 N2 110.79(15) . . ? C1 N1 H1 127(2) . . ? N2 N1 H1 123(2) . . ? N3 N2 N1 107.50(16) . . ? N2 N3 N4 107.75(17) . . ? C1 N4 N3 110.64(17) . . ? C1 N4 H4 130(2) . . ? N3 N4 H4 120(2) . . ? C1 N5 H5B 117.9(17) . . ? C1 N5 H5A 118.6(17) . . ? H5B N5 H5A 123(2) . . ? N5 C1 N4 127.84(18) . . ? N5 C1 N1 128.85(18) . . ? N4 C1 N1 103.31(17) . . ? O3 N8 O4 122.81(17) . . ? O3 N8 N7 125.56(17) . . ? O4 N8 N7 111.54(14) . . ? O1 N6 O2 121.40(16) . . ? O1 N6 N7 126.20(16) . . ? O2 N6 N7 112.34(14) . . ? N6 N7 N8 114.69(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 C1 N1 N2 N3 -0.8(2) . . . . ? N1 N2 N3 N4 0.0(2) . . . . ? N2 N3 N4 C1 0.8(2) . . . . ? N3 N4 C1 N5 179.1(2) . . . . ? N3 N4 C1 N1 -1.2(2) . . . . ? N2 N1 C1 N5 -179.1(2) . . . . ? N2 N1 C1 N4 1.2(2) . . . . ? O1 N6 N7 N8 13.4(3) . . . . ? O2 N6 N7 N8 -169.57(15) . . . . ? O3 N8 N7 N6 14.7(3) . . . . ? O4 N8 N7 N6 -168.78(18) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 N1 H1 O1 0.87(3) 2.23(3) 2.853(2) 128(3) 1_554 N1 H1 N3 0.87(3) 2.47(3) 3.122(2) 132(3) 2_534 N4 H4 O2 0.82(3) 2.07(3) 2.845(2) 158(3) . N4 H4 N7 0.82(3) 2.64(3) 3.209(2) 128(2) . N5 H5B O1 0.90(3) 2.20(3) 2.881(2) 132(2) 1_554 N5 H5B O4 0.90(3) 2.31(3) 2.970(2) 130(2) 2_644 N5 H5B O3 0.90(3) 2.53(3) 3.297(2) 142.8(19) 1_554 N5 H5A O4 0.91(3) 2.06(3) 2.902(3) 154(2) 1_655 N5 H5A O3 0.91(3) 2.57(3) 3.096(2) 117(2) 2_644 _geom_special_details ? # Attachment 'dx125a_2MeHATDN.cif' data_dx125 _database_code_depnum_ccdc_archive 'CCDC 693659' _audit_creation_method SHELXL-97 _audit_creation_date ; 'Mon Mar 31 18:10:27 2008' ; _audit_update_record 16.05.2008 _chemical_name_systematic '2-Methyl-5-aminotetrazolium dinitramide' _chemical_compound_source ? _chemical_name_common '2-Methyl-5-aminotetrazolium dinitramide' _chemical_formula_moiety 'C2 H6 N5, N3 O4' _chemical_formula_sum 'C2 H6 N8 O4' _chemical_formula_weight 206.15 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 2047 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0984 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 25.49 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.984 _reflns_number_total 1513 _reflns_number_gt 778 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.1072631763 _diffrn_orient_matrix_UB_12 0.0736435390 _diffrn_orient_matrix_UB_13 0.0317686634 _diffrn_orient_matrix_UB_21 0.0286646076 _diffrn_orient_matrix_UB_22 -0.0490620949 _diffrn_orient_matrix_UB_23 -0.0676068824 _diffrn_orient_matrix_UB_31 -0.0299267588 _diffrn_orient_matrix_UB_32 0.0680698476 _diffrn_orient_matrix_UB_33 -0.0292490534 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall -P1 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6567(8) _cell_length_b 7.2645(10) _cell_length_c 9.8178(12) _cell_angle_alpha 110.745(12) _cell_angle_beta 97.586(10) _cell_angle_gamma 105.950(11) _cell_volume 412.77(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 664 _cell_measurement_theta_min 4.0938 _cell_measurement_theta_max 33.4015 _cell_special_details ? _exptl_crystal_description rods _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93111 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.190 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.049 _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 SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _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_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1513 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 0.862 _refine_ls_restrained_S_all 0.862 _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 H4 H 0.077(4) -0.331(4) 0.323(3) 0.035(8) Uiso 1 1 d . . . H5B H 0.196(4) 0.223(5) 0.415(3) 0.055(10) Uiso 1 1 d . . . H2A H -0.208(4) -0.265(4) -0.125(3) 0.052(9) Uiso 1 1 d . . . H5A H 0.252(4) 0.075(4) 0.491(3) 0.040(9) Uiso 1 1 d . . . H2C H -0.345(4) -0.479(4) -0.114(3) 0.036(8) Uiso 1 1 d . . . H2B H -0.402(5) -0.268(5) -0.057(3) 0.071(11) Uiso 1 1 d . . . N7 N 0.2979(3) 0.8330(3) 0.5738(2) 0.0259(5) Uani 1 1 d . . . O4 O 0.4479(3) 1.1632(3) 0.71909(19) 0.0356(5) Uani 1 1 d . . . N4 N 0.0250(3) -0.2707(3) 0.2645(2) 0.0261(5) Uani 1 1 d . . . O1 O 0.1692(3) 0.5068(2) 0.41510(19) 0.0314(5) Uani 1 1 d . . . N5 N 0.1941(4) 0.0974(4) 0.4125(3) 0.0298(6) Uani 1 1 d . . . O2 O 0.3692(3) 0.5727(3) 0.6318(2) 0.0418(6) Uani 1 1 d . . . N3 N -0.1117(3) -0.3964(3) 0.1281(2) 0.0297(6) Uani 1 1 d . . . N8 N 0.4220(3) 0.9854(3) 0.7157(2) 0.0302(6) Uani 1 1 d . . . C1 C 0.0663(4) -0.0675(4) 0.2892(3) 0.0209(6) Uani 1 1 d . . . O3 O 0.4916(3) 0.9518(3) 0.8209(2) 0.0456(6) Uani 1 1 d . . . N1 N -0.0404(3) -0.0590(3) 0.1692(2) 0.0265(5) Uani 1 1 d . . . N6 N 0.2840(3) 0.6338(3) 0.5478(2) 0.0285(5) Uani 1 1 d . . . N2 N -0.1442(3) -0.2619(3) 0.0784(2) 0.0250(5) Uani 1 1 d . . . C2 C -0.2900(6) -0.3254(5) -0.0679(3) 0.0374(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N7 0.0317(13) 0.0191(12) 0.0254(13) 0.0091(10) 0.0021(10) 0.0088(10) O4 0.0387(11) 0.0185(10) 0.0394(13) 0.0067(8) 0.0043(9) 0.0043(8) N4 0.0304(13) 0.0231(13) 0.0239(13) 0.0111(10) 0.0030(11) 0.0078(10) O1 0.0362(11) 0.0231(10) 0.0269(11) 0.0060(8) 0.0013(9) 0.0070(8) N5 0.0343(14) 0.0261(14) 0.0294(16) 0.0132(12) 0.0027(11) 0.0113(12) O2 0.0512(13) 0.0321(11) 0.0422(13) 0.0195(10) -0.0041(10) 0.0165(10) N3 0.0372(14) 0.0255(13) 0.0283(14) 0.0133(11) 0.0079(11) 0.0111(11) N8 0.0280(13) 0.0264(13) 0.0314(14) 0.0084(10) 0.0038(11) 0.0085(10) C1 0.0222(14) 0.0199(14) 0.0207(15) 0.0091(12) 0.0059(12) 0.0060(11) O3 0.0621(15) 0.0452(13) 0.0292(12) 0.0133(10) -0.0020(10) 0.0268(11) N1 0.0281(12) 0.0217(12) 0.0257(13) 0.0076(10) 0.0039(10) 0.0070(9) N6 0.0287(13) 0.0266(13) 0.0351(15) 0.0161(11) 0.0096(11) 0.0115(10) N2 0.0295(12) 0.0199(12) 0.0230(12) 0.0079(9) 0.0062(10) 0.0061(10) C2 0.042(2) 0.0295(18) 0.0264(17) 0.0096(14) -0.0074(15) 0.0019(16) 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 N6 1.351(3) . ? N7 N8 1.396(3) . ? O4 N8 1.243(2) . ? N4 N3 1.345(3) . ? N4 C1 1.349(3) . ? N4 H4 0.92(2) . ? O1 N6 1.277(2) . ? N5 C1 1.329(3) . ? N5 H5B 0.90(3) . ? N5 H5A 0.90(3) . ? O2 N6 1.214(2) . ? N3 N2 1.291(3) . ? N8 O3 1.207(2) . ? C1 N1 1.323(3) . ? N1 N2 1.338(2) . ? N2 C2 1.461(3) . ? C2 H2A 0.96(3) . ? C2 H2C 0.98(3) . ? C2 H2B 0.95(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 N6 N7 N8 115.7(2) . . ? N3 N4 C1 110.2(2) . . ? N3 N4 H4 118.8(15) . . ? C1 N4 H4 130.9(15) . . ? C1 N5 H5B 115.2(17) . . ? C1 N5 H5A 118.6(16) . . ? H5B N5 H5A 125(2) . . ? N2 N3 N4 101.88(19) . . ? O3 N8 O4 124.5(2) . . ? O3 N8 N7 125.7(2) . . ? O4 N8 N7 109.8(2) . . ? N1 C1 N5 125.4(2) . . ? N1 C1 N4 108.6(2) . . ? N5 C1 N4 126.0(2) . . ? C1 N1 N2 102.68(18) . . ? O2 N6 O1 121.2(2) . . ? O2 N6 N7 127.8(2) . . ? O1 N6 N7 110.99(19) . . ? N3 N2 N1 116.58(19) . . ? N3 N2 C2 122.3(2) . . ? N1 N2 C2 121.1(2) . . ? N2 C2 H2A 107.7(16) . . ? N2 C2 H2C 106.5(14) . . ? H2A C2 H2C 113(2) . . ? N2 C2 H2B 111.1(18) . . ? H2A C2 H2B 106(3) . . ? H2C C2 H2B 113(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 N4 N3 N2 0.3(3) . . . . ? N6 N7 N8 O3 -10.4(3) . . . . ? N6 N7 N8 O4 170.7(2) . . . . ? N3 N4 C1 N1 -0.7(3) . . . . ? N3 N4 C1 N5 179.8(2) . . . . ? N5 C1 N1 N2 -179.7(2) . . . . ? N4 C1 N1 N2 0.8(3) . . . . ? N8 N7 N6 O2 -1.4(4) . . . . ? N8 N7 N6 O1 -179.40(18) . . . . ? N4 N3 N2 N1 0.3(3) . . . . ? N4 N3 N2 C2 -178.3(3) . . . . ? C1 N1 N2 N3 -0.8(3) . . . . ? C1 N1 N2 C2 177.9(2) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 N5 H5B O1 0.90(3) 2.12(3) 3.015(3) 175(2) . N5 H5B O2 0.90(3) 2.49(3) 3.126(3) 128(2) . N5 H5A O4 0.90(3) 2.21(3) 3.055(3) 156(2) 1_545 N5 H5A N7 0.90(3) 2.26(3) 3.044(3) 146(2) 1_545 _geom_special_details ? # Attachment 'dx264_HTzClO4.cif' data_dx264 _database_code_depnum_ccdc_archive 'CCDC 693660' _audit_creation_method SHELXL-97 _audit_creation_date ; 'Thu Jun 26 15:28:00 2008' ; _audit_update_record 26-05-2008 _chemical_name_systematic 'Tetrazolium Perchlorate' _chemical_compound_source ? _chemical_name_common 'Tetrazolium Perchlorate' _chemical_formula_moiety 'C H3 N4, Cl O4' _chemical_formula_sum 'C1 H3 Cl N4 O4' _chemical_formula_weight 170.52 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 5406 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0136 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 27.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 1231 _reflns_number_gt 1071 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0223968212 _diffrn_orient_matrix_UB_12 -0.0306317233 _diffrn_orient_matrix_UB_13 0.0433391988 _diffrn_orient_matrix_UB_21 -0.1365622296 _diffrn_orient_matrix_UB_22 -0.0199738772 _diffrn_orient_matrix_UB_23 -0.0124504030 _diffrn_orient_matrix_UB_31 0.0390725487 _diffrn_orient_matrix_UB_32 -0.0874000212 _diffrn_orient_matrix_UB_33 -0.0123301977 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 4.9338(4) _cell_length_b 7.4893(5) _cell_length_c 15.1744(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.073(6) _cell_angle_gamma 90.00 _cell_volume 560.34(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 4130 _cell_measurement_theta_min 3.8185 _cell_measurement_theta_max 32.4083 _cell_special_details ? _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.021 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.642 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89746 _exptl_absorpt_correction_T_max 0.96000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.224 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.053 _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 SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(3) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1231 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 Cl1 Cl 0.39246(7) 0.21862(5) 0.09381(2) 0.02011(15) Uani 1 1 d . . . O4 O 0.2742(2) 0.05472(14) 0.06177(8) 0.0303(3) Uani 1 1 d . . . O3 O 0.6830(2) 0.20020(15) 0.10164(8) 0.0317(3) Uani 1 1 d . . . O1 O 0.2872(3) 0.26080(16) 0.17897(8) 0.0314(3) Uani 1 1 d . . . O2 O 0.3240(3) 0.36166(15) 0.03418(8) 0.0355(3) Uani 1 1 d . . . N2 N 0.8284(3) 0.27468(18) 0.31704(9) 0.0277(3) Uani 1 1 d . . . N1 N 0.6268(3) 0.33683(19) 0.36607(9) 0.0251(3) Uani 1 1 d . . . N3 N 0.7814(3) 0.10963(18) 0.30299(9) 0.0300(3) Uani 1 1 d . . . N4 N 0.5510(3) 0.06804(19) 0.34326(9) 0.0260(3) Uani 1 1 d . . . C1 C 0.4567(3) 0.2085(2) 0.38243(11) 0.0255(3) Uani 1 1 d . . . H2 H 0.489(4) -0.031(3) 0.3404(13) 0.035(5) Uiso 1 1 d . . . H3 H 0.306(5) 0.215(3) 0.4118(16) 0.050(6) Uiso 1 1 d . . . H1 H 0.623(4) 0.437(3) 0.3822(14) 0.043(6) 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 Cl1 0.0194(2) 0.0178(2) 0.0232(2) 0.00045(13) 0.00084(13) -0.00047(12) O4 0.0282(6) 0.0222(6) 0.0408(7) -0.0055(5) 0.0050(5) -0.0075(5) O3 0.0188(6) 0.0287(6) 0.0475(7) -0.0062(5) 0.0012(5) 0.0002(4) O1 0.0323(6) 0.0377(7) 0.0244(6) -0.0029(5) 0.0034(5) 0.0090(5) O2 0.0443(7) 0.0272(6) 0.0345(6) 0.0117(5) -0.0061(5) -0.0025(5) N2 0.0272(7) 0.0238(7) 0.0325(7) -0.0019(6) 0.0050(6) -0.0017(5) N1 0.0288(7) 0.0187(7) 0.0277(7) -0.0033(5) 0.0002(5) 0.0014(5) N3 0.0318(7) 0.0231(7) 0.0355(8) -0.0014(6) 0.0071(6) 0.0010(6) N4 0.0297(7) 0.0195(7) 0.0288(7) 0.0010(5) 0.0005(5) -0.0052(6) C1 0.0219(8) 0.0288(9) 0.0256(8) 0.0017(6) 0.0006(6) 0.0006(6) 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 Cl1 O2 1.4346(11) . ? Cl1 O4 1.4363(11) . ? Cl1 O3 1.4407(11) . ? Cl1 O1 1.4451(12) . ? N2 N3 1.2742(18) . ? N2 N1 1.3466(19) . ? N1 C1 1.305(2) . ? N1 H1 0.79(2) . ? N3 N4 1.3463(19) . ? N4 C1 1.303(2) . ? N4 H2 0.80(2) . ? C1 H3 0.88(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 O2 Cl1 O4 109.95(7) . . ? O2 Cl1 O3 109.53(7) . . ? O4 Cl1 O3 109.69(7) . . ? O2 Cl1 O1 108.47(7) . . ? O4 Cl1 O1 109.55(7) . . ? O3 Cl1 O1 109.63(7) . . ? N3 N2 N1 107.11(12) . . ? C1 N1 N2 110.09(14) . . ? C1 N1 H1 128.1(16) . . ? N2 N1 H1 121.8(16) . . ? N2 N3 N4 107.46(12) . . ? C1 N4 N3 109.97(14) . . ? C1 N4 H2 129.0(14) . . ? N3 N4 H2 121.0(14) . . ? N4 C1 N1 105.38(15) . . ? N4 C1 H3 126.4(14) . . ? N1 C1 H3 128.1(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 N3 N2 N1 C1 0.37(18) . . . . ? N1 N2 N3 N4 -0.13(17) . . . . ? N2 N3 N4 C1 -0.16(19) . . . . ? N3 N4 C1 N1 0.38(18) . . . . ? N2 N1 C1 N4 -0.46(18) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 N4 H2 O1 0.80(2) 2.09(2) 2.8550(19) 160.9(19) 2_545 N4 H2 O2 0.80(2) 2.62(2) 3.0855(18) 118.5(17) 2_545 N4 H2 Cl1 0.80(2) 2.86(2) 3.5634(14) 147.2(18) 2_545 N1 H1 O3 0.79(2) 2.20(2) 2.9144(18) 151(2) 2_655 N1 H1 O4 0.79(2) 2.34(2) 2.8164(17) 120.1(19) 2 _geom_special_details ? # Attachment 'dx269a_HTzDN.cif' data_dx269 _database_code_depnum_ccdc_archive 'CCDC 693661' _audit_creation_method SHELXL-97 _audit_creation_date ; 'Mon Jun 30 18:25:02 2008' ; _audit_update_record 30.06.2008 _chemical_name_systematic '5H-tetrazolium dinitramide' _chemical_compound_source ? _chemical_name_common '5H-tetrazolium dinitramide' _chemical_formula_moiety 'N3 O4, C H3 N4' _chemical_formula_sum 'C H3 N7 O4' _chemical_formula_weight 177.10 _diffrn_ambient_temperature 200 # in K _diffrn_source_type 'Spellman generator' _diffrn_source_power ? # in kW _diffrn_source_voltage 50 # kV _diffrn_source_current 40 # mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.5 _diffrn_measurement_device 'CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method omega-scan _diffrn_radiation_type 'Mo K\a' _diffrn_detector_area_resol_mean 15.9809 _diffrn_reflns_number 2058 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.1269 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 29.23 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 29.23 _diffrn_measured_fraction_theta_full 0.990 _reflns_number_total 871 _reflns_number_gt 341 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0197668084 _diffrn_orient_matrix_UB_12 -0.0869294750 _diffrn_orient_matrix_UB_13 -0.0165920129 _diffrn_orient_matrix_UB_21 -0.0723716183 _diffrn_orient_matrix_UB_22 -0.0058358380 _diffrn_orient_matrix_UB_23 0.0388101550 _diffrn_orient_matrix_UB_31 -0.0707271308 _diffrn_orient_matrix_UB_32 0.0304491930 _diffrn_orient_matrix_UB_33 -0.0400645596 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' 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' 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 6.904(2) _cell_length_b 7.668(2) _cell_length_c 12.200(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.01(3) _cell_angle_gamma 90.00 _cell_volume 645.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 416 _cell_measurement_theta_min 3.9442 _cell_measurement_theta_max 29.9918 _cell_special_details ? _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93413 _exptl_absorpt_correction_T_max 0.99000 _exptl_absorpt_process_details ;SCALE3 ABSPACK - An Oxford Diffraction program (1.0.4,gui:1.0.3) (C) 2005 Oxford Diffraction Ltd. ; _exptl_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist ? ? ? ? _diffrn_special_details ? _refine_diff_density_max 0.155 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.038 _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 SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid # Plot Program for Crystal Structure Illustrations, Oak Ridge National # Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ. # Glasgow) used --- SCHAKAL (E. Keller, University of Freiburg (Breisgau), # Germany, 1995)' ; _computing_publication_material ;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version). # --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses). ; _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 871 _refine_ls_number_parameters 85 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0492 _refine_ls_goodness_of_fit_ref 0.752 _refine_ls_restrained_S_all 0.752 _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 N3 N 0.1029(3) 0.07820(18) 0.44487(13) 0.0359(4) Uani 1 1 d . . . N2 N 0.56526(19) 0.27141(15) 0.28899(11) 0.0420(4) Uani 1 1 d . . . C1 C 0.5000 0.0026(3) 0.2500 0.0363(6) Uani 1 2 d S . . N1 N 0.6054(2) 0.10424(18) 0.31348(11) 0.0366(4) Uani 1 1 d D . . N4 N -0.0798(4) 0.0389(3) 0.4663(2) 0.0317(7) Uani 0.50 1 d P . . O1A O 0.2533(5) 0.0247(5) 0.4894(3) 0.0523(12) Uani 0.488(6) 1 d P . 1 O2A O 0.1098(6) 0.1716(3) 0.3583(2) 0.0453(14) Uani 0.488(6) 1 d P . 1 O1B O -0.0300(6) 0.1570(3) 0.4015(3) 0.0590(15) Uani 0.512(6) 1 d P . 2 O2B O 0.2731(5) 0.0998(6) 0.4334(4) 0.0553(14) Uani 0.512(6) 1 d P . 2 H1 H 0.7024(18) 0.079(2) 0.3634(11) 0.060(6) Uiso 1 1 d D A 2 H2 H 0.5000 -0.123(3) 0.2500 0.049(7) Uiso 1 2 d S B 2 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 N3 0.0351(11) 0.0372(10) 0.0349(10) -0.0037(7) -0.0045(9) -0.0033(9) N2 0.0482(11) 0.0324(7) 0.0443(10) -0.0026(7) -0.0082(6) -0.0031(8) C1 0.0363(16) 0.0305(16) 0.0420(17) 0.000 0.0011(13) 0.000 N1 0.0380(9) 0.0394(9) 0.0313(9) 0.0061(8) -0.0077(7) 0.0009(8) N4 0.0232(19) 0.0441(19) 0.0275(17) 0.0045(15) -0.0020(12) 0.0002(14) O1A 0.0255(19) 0.083(3) 0.047(2) 0.0228(18) -0.0135(16) -0.0026(17) O2A 0.054(3) 0.0447(16) 0.0379(19) 0.0157(13) 0.0062(16) -0.0015(16) O1B 0.044(3) 0.0613(19) 0.069(2) 0.0340(16) -0.028(2) -0.0100(16) O2B 0.035(2) 0.074(3) 0.059(3) -0.022(2) 0.0106(17) -0.0107(18) 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 N3 O1B 1.198(3) . ? N3 O2B 1.202(3) . ? N3 O1A 1.218(3) . ? N3 O2A 1.280(3) . ? N3 N4 1.336(3) . ? N2 N1 1.3418(17) . ? C1 N1 1.2951(18) . ? C1 H2 0.96(2) . ? N1 H1 0.902(5) . ? N4 O1B 1.262(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1B N3 O2B 127.6(3) . . ? O1B N3 O1A 169.2(3) . . ? O1B N3 O2A 54.12(18) . . ? O2B N3 O2A 75.4(3) . . ? O1A N3 O2A 119.3(3) . . ? O1B N3 N4 59.4(2) . . ? O2B N3 N4 173.0(4) . . ? O1A N3 N4 129.0(3) . . ? O2A N3 N4 111.4(3) . . ? O1B N3 N4 122.7(3) . 5_556 ? O2B N3 N4 108.9(3) . 5_556 ? O1A N3 N4 64.8(3) . 5_556 ? O2A N3 N4 173.2(2) . 5_556 ? N4 N3 N4 64.2(2) . 5_556 ? N2 N2 N1 107.19(8) 2_655 . ? N1 C1 N1 106.0(2) . 2_655 ? N1 C1 H2 126.99(11) . . ? N1 C1 H2 126.99(10) 2_655 . ? C1 N1 N2 109.80(15) . . ? C1 N1 H1 130.5(11) . . ? N2 N1 H1 119.4(11) . . ? O1B N4 N3 54.8(2) . . ? O1B N4 N3 167.2(3) . 5_556 ? N3 N4 N3 115.8(2) . 5_556 ? O1B N4 O1A 138.2(3) . 5_556 ? N3 N4 O1A 166.4(3) . 5_556 ? N3 N4 O1A 50.61(19) 5_556 5_556 ? O1B N4 N4 114.9(4) . 5_556 ? N3 N4 N4 60.8(2) . 5_556 ? N3 N4 N4 55.1(2) 5_556 5_556 ? O1A N4 N4 105.7(3) 5_556 5_556 ? N3 O1A N4 64.6(2) . 5_556 ? N3 O1B N4 65.7(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 N1 C1 N1 N2 -0.12(8) 2_655 . . . ? N2 N2 N1 C1 0.3(2) 2_655 . . . ? O1A N3 N4 O1B 171.6(3) . . . . ? O2A N3 N4 O1B -15.8(3) . . . . ? N4 N3 N4 O1B 169.8(3) 5_556 . . . ? O1B N3 N4 N3 -169.8(3) . . . 5_556 ? O1A N3 N4 N3 1.8(3) . . . 5_556 ? O2A N3 N4 N3 174.4(2) . . . 5_556 ? N4 N3 N4 N3 0.0 5_556 . . 5_556 ? O1B N3 N4 O1A -164.7(11) . . . 5_556 ? O1A N3 N4 O1A 6.9(13) . . . 5_556 ? O2A N3 N4 O1A 179.4(10) . . . 5_556 ? N4 N3 N4 O1A 5.1(10) 5_556 . . 5_556 ? O1B N3 N4 N4 -169.8(3) . . . 5_556 ? O1A N3 N4 N4 1.8(3) . . . 5_556 ? O2A N3 N4 N4 174.4(2) . . . 5_556 ? O1B N3 O1A N4 136.3(16) . . . 5_556 ? O2B N3 O1A N4 179.5(4) . . . 5_556 ? O2A N3 O1A N4 -173.9(2) . . . 5_556 ? N4 N3 O1A N4 -1.8(3) . . . 5_556 ? O2B N3 O1B N4 -179.9(3) . . . . ? O1A N3 O1B N4 -142.9(16) . . . . ? O2A N3 O1B N4 161.7(3) . . . . ? N4 N3 O1B N4 -10.9(3) 5_556 . . . ? N3 N4 O1B N3 46.0(14) 5_556 . . . ? O1A N4 O1B N3 174.7(4) 5_556 . . . ? N4 N4 O1B N3 9.8(3) 5_556 . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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 ? ? ? ? ? ? ? ? _geom_special_details ?