Supplementary material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name D.A.Parrish J.Shreeve Y.Zhang _publ_contact_author_name 'Dr Damon A. Parrish' _publ_contact_author_email damon.parrish@nrl.navy.mil data_shrv139 _database_code_depnum_ccdc_archive 'CCDC 799952' #TrackingRef 'shrv139-final.cif' _audit_creation_date 2010-10-27 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 1-amino-4-methyl-1H-tetrazol-5(4H)-iminium 4-amino-3,5-dinitropyrazol-1-ide ; _chemical_name_common ;1-amino-4-methyl-1H-tetrazol-5(4H)-iminium 4-amino-3,5- dinitropyrazol-1-ide ; _chemical_melting_point ? _chemical_formula_moiety 'C2 H7 N6 1+, C3 H2 N5 O4 1-' _chemical_formula_sum 'C5 H9 N11 O4' _chemical_formula_weight 287.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7105(9) _cell_length_b 11.6875(15) _cell_length_c 15.534(2) _cell_angle_alpha 79.793(2) _cell_angle_beta 85.714(2) _cell_angle_gamma 74.038(2) _cell_volume 1152.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.71 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9060 _exptl_absorpt_correction_T_max 0.9640 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10367 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 26.44 _reflns_number_total 4712 _reflns_number_gt 4099 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.3485P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4712 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 N1A N 0.29312(18) 0.07177(10) 0.82452(7) 0.0199(2) Uani 1 1 d . . . N2A N 0.19544(18) 0.11858(11) 0.74664(8) 0.0229(3) Uani 1 1 d . . . N3A N 0.07841(19) 0.05298(11) 0.73701(8) 0.0239(3) Uani 1 1 d . . . N4A N 0.09893(18) -0.03754(11) 0.80814(8) 0.0209(3) Uani 1 1 d . . . C5A C 0.2356(2) -0.02741(12) 0.86245(9) 0.0192(3) Uani 1 1 d . . . N6A N 0.4564(2) 0.10686(12) 0.85248(9) 0.0233(3) Uani 1 1 d . . . H6AA H 0.552(3) 0.1023(16) 0.8067(12) 0.028 Uiso 1 1 d . . . H6AB H 0.408(3) 0.1777(18) 0.8659(11) 0.028 Uiso 1 1 d . . . C7A C -0.0144(2) -0.12895(14) 0.81521(11) 0.0276(3) Uani 1 1 d . . . H7AA H 0.0180 -0.1848 0.8704 0.041 Uiso 1 1 calc R . . H7AB H 0.0262 -0.1737 0.7661 0.041 Uiso 1 1 calc R . . H7AC H -0.1637 -0.0899 0.8138 0.041 Uiso 1 1 calc R . . N8A N 0.2995(2) -0.09586(11) 0.93705(8) 0.0257(3) Uani 1 1 d . . . H8AA H 0.2504 -0.1583 0.9571 0.031 Uiso 1 1 calc R . . H8AB H 0.3914 -0.0793 0.9670 0.031 Uiso 1 1 calc R . . N9A N 0.26457(17) 0.58556(10) -0.06459(7) 0.0175(2) Uani 1 1 d . . . N10A N 0.23376(17) 0.66804(10) -0.01317(7) 0.0177(2) Uani 1 1 d . . . C11A C 0.2096(2) 0.61377(12) 0.07106(8) 0.0164(3) Uani 1 1 d . . . C12A C 0.22782(19) 0.49008(12) 0.07655(9) 0.0165(3) Uani 1 1 d . . . C13A C 0.26095(19) 0.47871(12) -0.01256(9) 0.0160(3) Uani 1 1 d . . . N14A N 0.17501(17) 0.67966(11) 0.14003(7) 0.0189(2) Uani 1 1 d . . . O15A O 0.18029(17) 0.78672(9) 0.12575(7) 0.0262(2) Uani 1 1 d . . . O16A O 0.14066(16) 0.62584(9) 0.21452(6) 0.0232(2) Uani 1 1 d . . . N17A N 0.21532(19) 0.40629(11) 0.14618(8) 0.0219(3) Uani 1 1 d . . . H17A H 0.1922 0.4263 0.1988 0.026 Uiso 1 1 calc R . . H17B H 0.2302 0.3312 0.1394 0.026 Uiso 1 1 calc R . . N18A N 0.28968(17) 0.37301(10) -0.04740(7) 0.0179(2) Uani 1 1 d . . . O19A O 0.28742(16) 0.27842(9) 0.00451(7) 0.0236(2) Uani 1 1 d . . . O20A O 0.31627(16) 0.37489(9) -0.12779(6) 0.0242(2) Uani 1 1 d . . . N1B N 0.27357(18) 0.55269(10) 0.70330(7) 0.0190(2) Uani 1 1 d . . . N2B N 0.06822(18) 0.60458(11) 0.68724(8) 0.0215(3) Uani 1 1 d . . . N3B N 0.00932(19) 0.54058(11) 0.64089(8) 0.0224(3) Uani 1 1 d . . . N4B N 0.17714(19) 0.44717(11) 0.62609(8) 0.0208(3) Uani 1 1 d . . . C5B C 0.3435(2) 0.45424(12) 0.66500(8) 0.0194(3) Uani 1 1 d . . . N6B N 0.4004(2) 0.59678(12) 0.74718(8) 0.0217(3) Uani 1 1 d . . . H6BA H 0.354(3) 0.5991(16) 0.8019(12) 0.026 Uiso 1 1 d . . . H6BB H 0.407(3) 0.6654(17) 0.7198(12) 0.026 Uiso 1 1 d . . . C7B C 0.1598(3) 0.35732(14) 0.57497(10) 0.0281(3) Uani 1 1 d . . . H7BA H 0.2130 0.2764 0.6085 0.042 Uiso 1 1 calc R . . H7BB H 0.2408 0.3653 0.5201 0.042 Uiso 1 1 calc R . . H7BC H 0.0140 0.3698 0.5619 0.042 Uiso 1 1 calc R . . N8B N 0.53321(19) 0.38425(11) 0.66626(8) 0.0242(3) Uani 1 1 d . . . H8BA H 0.5651 0.3219 0.6385 0.029 Uiso 1 1 calc R . . H8BB H 0.6288 0.3996 0.6948 0.029 Uiso 1 1 calc R . . N9B N 0.35403(17) 0.84797(10) 0.38420(7) 0.0179(2) Uani 1 1 d . . . N10B N 0.38255(17) 0.94180(10) 0.32837(7) 0.0184(2) Uani 1 1 d . . . C11B C 0.3365(2) 1.03792(12) 0.37209(9) 0.0176(3) Uani 1 1 d . . . C12B C 0.27316(19) 1.00762(12) 0.45954(9) 0.0169(3) Uani 1 1 d . . . C13B C 0.2895(2) 0.88473(12) 0.46278(9) 0.0167(3) Uani 1 1 d . . . N14B N 0.37322(17) 1.14785(11) 0.33334(8) 0.0199(3) Uani 1 1 d . . . O15B O 0.44068(16) 1.16109(9) 0.25632(7) 0.0261(2) Uani 1 1 d . . . O16B O 0.33952(16) 1.22943(9) 0.37897(7) 0.0257(2) Uani 1 1 d . . . N17B N 0.21587(18) 1.07671(11) 0.52233(8) 0.0214(3) Uani 1 1 d . . . H17C H 0.1814 1.0450 0.5751 0.026 Uiso 1 1 calc R . . H17D H 0.2128 1.1536 0.5107 0.026 Uiso 1 1 calc R . . N18B N 0.25707(17) 0.80220(11) 0.53575(7) 0.0193(2) Uani 1 1 d . . . O19B O 0.20072(15) 0.84133(10) 0.60601(6) 0.0238(2) Uani 1 1 d . . . O20B O 0.28688(17) 0.69484(9) 0.52842(7) 0.0280(2) 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 N1A 0.0233(6) 0.0148(6) 0.0196(6) -0.0005(5) -0.0004(5) -0.0036(5) N2A 0.0233(6) 0.0181(6) 0.0226(6) 0.0007(5) 0.0006(5) -0.0009(5) N3A 0.0248(6) 0.0203(6) 0.0224(6) 0.0019(5) -0.0014(5) -0.0021(5) N4A 0.0231(6) 0.0154(6) 0.0222(6) 0.0008(5) -0.0032(5) -0.0034(5) C5A 0.0223(7) 0.0124(6) 0.0210(7) -0.0018(5) 0.0008(5) -0.0024(5) N6A 0.0280(7) 0.0160(6) 0.0277(7) -0.0042(5) 0.0011(5) -0.0088(5) C7A 0.0292(8) 0.0212(8) 0.0332(8) 0.0023(6) -0.0098(6) -0.0100(6) N8A 0.0335(7) 0.0198(6) 0.0257(6) 0.0036(5) -0.0095(5) -0.0128(5) N9A 0.0181(5) 0.0157(6) 0.0182(6) -0.0027(4) -0.0015(4) -0.0037(4) N10A 0.0188(5) 0.0157(6) 0.0175(5) -0.0018(5) -0.0014(4) -0.0033(4) C11A 0.0169(6) 0.0152(7) 0.0168(6) -0.0021(5) -0.0011(5) -0.0036(5) C12A 0.0127(6) 0.0172(7) 0.0194(6) -0.0014(5) -0.0012(5) -0.0041(5) C13A 0.0152(6) 0.0146(7) 0.0186(6) -0.0028(5) -0.0010(5) -0.0044(5) N14A 0.0193(6) 0.0180(6) 0.0192(6) -0.0028(5) -0.0006(4) -0.0046(5) O15A 0.0360(6) 0.0168(5) 0.0274(5) -0.0058(4) 0.0027(4) -0.0093(4) O16A 0.0287(5) 0.0239(5) 0.0161(5) -0.0012(4) 0.0013(4) -0.0072(4) N17A 0.0307(6) 0.0162(6) 0.0188(6) -0.0005(5) 0.0022(5) -0.0087(5) N18A 0.0167(5) 0.0159(6) 0.0212(6) -0.0025(5) -0.0018(4) -0.0046(4) O19A 0.0289(5) 0.0156(5) 0.0269(5) -0.0005(4) -0.0002(4) -0.0090(4) O20A 0.0324(6) 0.0218(5) 0.0190(5) -0.0057(4) -0.0009(4) -0.0068(4) N1B 0.0262(6) 0.0134(6) 0.0157(5) -0.0011(4) 0.0000(4) -0.0033(5) N2B 0.0258(6) 0.0177(6) 0.0186(6) 0.0005(5) 0.0025(5) -0.0047(5) N3B 0.0257(6) 0.0176(6) 0.0216(6) 0.0008(5) 0.0012(5) -0.0048(5) N4B 0.0271(6) 0.0140(6) 0.0200(6) -0.0008(5) -0.0025(5) -0.0039(5) C5B 0.0294(7) 0.0140(7) 0.0144(6) -0.0001(5) -0.0005(5) -0.0067(6) N6B 0.0328(7) 0.0160(6) 0.0178(6) -0.0026(5) 0.0003(5) -0.0093(5) C7B 0.0392(9) 0.0178(8) 0.0286(8) -0.0054(6) -0.0108(7) -0.0063(6) N8B 0.0286(7) 0.0183(6) 0.0253(6) -0.0085(5) -0.0068(5) -0.0009(5) N9B 0.0204(6) 0.0140(6) 0.0180(6) -0.0006(4) -0.0002(4) -0.0037(4) N10B 0.0195(6) 0.0140(6) 0.0203(6) -0.0001(5) -0.0011(4) -0.0035(4) C11B 0.0158(6) 0.0139(7) 0.0221(7) -0.0008(5) -0.0019(5) -0.0034(5) C12B 0.0120(6) 0.0168(7) 0.0215(7) -0.0032(5) -0.0024(5) -0.0026(5) C13B 0.0159(6) 0.0152(7) 0.0181(6) -0.0008(5) -0.0014(5) -0.0037(5) N14B 0.0170(6) 0.0153(6) 0.0260(6) 0.0008(5) -0.0040(5) -0.0036(4) O15B 0.0292(5) 0.0215(6) 0.0257(5) 0.0043(4) 0.0004(4) -0.0089(4) O16B 0.0269(5) 0.0134(5) 0.0371(6) -0.0055(4) -0.0033(4) -0.0047(4) N17B 0.0234(6) 0.0185(6) 0.0230(6) -0.0075(5) 0.0005(5) -0.0045(5) N18B 0.0192(6) 0.0178(6) 0.0200(6) -0.0010(5) 0.0002(4) -0.0047(5) O19B 0.0262(5) 0.0272(6) 0.0171(5) -0.0037(4) 0.0022(4) -0.0064(4) O20B 0.0409(6) 0.0153(5) 0.0269(6) 0.0001(4) 0.0036(5) -0.0092(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1A C5A 1.3452(19) . ? N1A N2A 1.3708(17) . ? N1A N6A 1.3921(17) . ? N2A N3A 1.2714(18) . ? N3A N4A 1.3738(17) . ? N4A C5A 1.3334(18) . ? N4A C7A 1.4578(19) . ? C5A N8A 1.3130(19) . ? N6A H6AA 0.919(18) . ? N6A H6AB 0.858(19) . ? C7A H7AA 0.9800 . ? C7A H7AB 0.9800 . ? C7A H7AC 0.9800 . ? N8A H8AA 0.8800 . ? N8A H8AB 0.8800 . ? N9A N10A 1.3225(16) . ? N9A C13A 1.3672(18) . ? N10A C11A 1.3680(17) . ? C11A N14A 1.3971(17) . ? C11A C12A 1.4045(19) . ? C12A N17A 1.3387(18) . ? C12A C13A 1.4094(18) . ? C13A N18A 1.3952(17) . ? N14A O15A 1.2413(15) . ? N14A O16A 1.2528(15) . ? N17A H17A 0.8800 . ? N17A H17B 0.8800 . ? N18A O20A 1.2453(15) . ? N18A O19A 1.2507(15) . ? N1B C5B 1.3425(18) . ? N1B N2B 1.3664(16) . ? N1B N6B 1.3809(17) . ? N2B N3B 1.2768(17) . ? N3B N4B 1.3737(17) . ? N4B C5B 1.3371(19) . ? N4B C7B 1.4572(18) . ? C5B N8B 1.3098(19) . ? N6B H6BA 0.887(18) . ? N6B H6BB 0.85(2) . ? C7B H7BA 0.9800 . ? C7B H7BB 0.9800 . ? C7B H7BC 0.9800 . ? N8B H8BA 0.8800 . ? N8B H8BB 0.8800 . ? N9B N10B 1.3210(16) . ? N9B C13B 1.3662(17) . ? N10B C11B 1.3664(17) . ? C11B N14B 1.3970(18) . ? C11B C12B 1.4062(19) . ? C12B N17B 1.3430(17) . ? C12B C13B 1.4022(19) . ? C13B N18B 1.3977(18) . ? N14B O15B 1.2460(16) . ? N14B O16B 1.2488(15) . ? N17B H17C 0.8800 . ? N17B H17D 0.8800 . ? N18B O20B 1.2396(16) . ? N18B O19B 1.2504(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5A N1A N2A 110.03(12) . . ? C5A N1A N6A 123.93(12) . . ? N2A N1A N6A 124.99(12) . . ? N3A N2A N1A 107.52(12) . . ? N2A N3A N4A 108.31(11) . . ? C5A N4A N3A 109.79(12) . . ? C5A N4A C7A 129.02(12) . . ? N3A N4A C7A 121.16(12) . . ? N8A C5A N4A 128.91(13) . . ? N8A C5A N1A 126.76(13) . . ? N4A C5A N1A 104.33(12) . . ? N1A N6A H6AA 105.1(11) . . ? N1A N6A H6AB 108.1(12) . . ? H6AA N6A H6AB 114.6(17) . . ? N4A C7A H7AA 109.5 . . ? N4A C7A H7AB 109.5 . . ? H7AA C7A H7AB 109.5 . . ? N4A C7A H7AC 109.5 . . ? H7AA C7A H7AC 109.5 . . ? H7AB C7A H7AC 109.5 . . ? C5A N8A H8AA 120.0 . . ? C5A N8A H8AB 120.0 . . ? H8AA N8A H8AB 120.0 . . ? N10A N9A C13A 107.42(11) . . ? N9A N10A C11A 108.17(11) . . ? N10A C11A N14A 120.84(12) . . ? N10A C11A C12A 111.94(11) . . ? N14A C11A C12A 127.21(12) . . ? N17A C12A C11A 130.28(12) . . ? N17A C12A C13A 129.54(13) . . ? C11A C12A C13A 100.18(11) . . ? N9A C13A N18A 121.55(12) . . ? N9A C13A C12A 112.28(11) . . ? N18A C13A C12A 126.17(13) . . ? O15A N14A O16A 123.10(11) . . ? O15A N14A C11A 119.70(12) . . ? O16A N14A C11A 117.20(11) . . ? C12A N17A H17A 120.0 . . ? C12A N17A H17B 120.0 . . ? H17A N17A H17B 120.0 . . ? O20A N18A O19A 122.13(11) . . ? O20A N18A C13A 120.04(12) . . ? O19A N18A C13A 117.84(11) . . ? C5B N1B N2B 110.49(11) . . ? C5B N1B N6B 122.98(12) . . ? N2B N1B N6B 126.39(11) . . ? N3B N2B N1B 107.53(11) . . ? N2B N3B N4B 107.93(11) . . ? C5B N4B N3B 110.06(11) . . ? C5B N4B C7B 128.66(12) . . ? N3B N4B C7B 121.28(12) . . ? N8B C5B N4B 129.55(13) . . ? N8B C5B N1B 126.46(13) . . ? N4B C5B N1B 103.99(12) . . ? N1B N6B H6BA 109.4(11) . . ? N1B N6B H6BB 109.5(11) . . ? H6BA N6B H6BB 112.8(16) . . ? N4B C7B H7BA 109.5 . . ? N4B C7B H7BB 109.5 . . ? H7BA C7B H7BB 109.5 . . ? N4B C7B H7BC 109.5 . . ? H7BA C7B H7BC 109.5 . . ? H7BB C7B H7BC 109.5 . . ? C5B N8B H8BA 120.0 . . ? C5B N8B H8BB 120.0 . . ? H8BA N8B H8BB 120.0 . . ? N10B N9B C13B 108.14(11) . . ? N9B N10B C11B 107.36(11) . . ? N10B C11B N14B 121.12(12) . . ? N10B C11B C12B 112.32(12) . . ? N14B C11B C12B 126.21(12) . . ? N17B C12B C13B 130.03(13) . . ? N17B C12B C11B 129.79(13) . . ? C13B C12B C11B 100.18(11) . . ? N9B C13B N18B 120.66(12) . . ? N9B C13B C12B 112.00(12) . . ? N18B C13B C12B 127.27(12) . . ? O15B N14B O16B 122.34(12) . . ? O15B N14B C11B 119.97(12) . . ? O16B N14B C11B 117.67(12) . . ? C12B N17B H17C 120.0 . . ? C12B N17B H17D 120.0 . . ? H17C N17B H17D 120.0 . . ? O20B N18B O19B 123.28(12) . . ? O20B N18B C13B 119.23(11) . . ? O19B N18B C13B 117.49(11) . . ? 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 C5A N1A N2A N3A 1.26(15) . . . . ? N6A N1A N2A N3A 169.90(12) . . . . ? N1A N2A N3A N4A -0.26(14) . . . . ? N2A N3A N4A C5A -0.84(15) . . . . ? N2A N3A N4A C7A -179.02(12) . . . . ? N3A N4A C5A N8A -179.60(14) . . . . ? C7A N4A C5A N8A -1.6(2) . . . . ? N3A N4A C5A N1A 1.55(15) . . . . ? C7A N4A C5A N1A 179.55(13) . . . . ? N2A N1A C5A N8A 179.40(13) . . . . ? N6A N1A C5A N8A 10.6(2) . . . . ? N2A N1A C5A N4A -1.71(14) . . . . ? N6A N1A C5A N4A -170.50(12) . . . . ? C13A N9A N10A C11A -0.32(13) . . . . ? N9A N10A C11A N14A 179.85(11) . . . . ? N9A N10A C11A C12A 0.88(15) . . . . ? N10A C11A C12A N17A 179.62(13) . . . . ? N14A C11A C12A N17A 0.7(2) . . . . ? N10A C11A C12A C13A -1.01(14) . . . . ? N14A C11A C12A C13A -179.89(12) . . . . ? N10A N9A C13A N18A -179.79(11) . . . . ? N10A N9A C13A C12A -0.35(14) . . . . ? N17A C12A C13A N9A -179.80(13) . . . . ? C11A C12A C13A N9A 0.82(14) . . . . ? N17A C12A C13A N18A -0.4(2) . . . . ? C11A C12A C13A N18A -179.77(12) . . . . ? N10A C11A N14A O15A -4.98(18) . . . . ? C12A C11A N14A O15A 173.81(12) . . . . ? N10A C11A N14A O16A 175.37(11) . . . . ? C12A C11A N14A O16A -5.84(19) . . . . ? N9A C13A N18A O20A -1.12(18) . . . . ? C12A C13A N18A O20A 179.51(12) . . . . ? N9A C13A N18A O19A 178.94(11) . . . . ? C12A C13A N18A O19A -0.42(19) . . . . ? C5B N1B N2B N3B 0.52(15) . . . . ? N6B N1B N2B N3B 176.33(13) . . . . ? N1B N2B N3B N4B -0.46(14) . . . . ? N2B N3B N4B C5B 0.25(15) . . . . ? N2B N3B N4B C7B 179.82(12) . . . . ? N3B N4B C5B N8B -179.27(14) . . . . ? C7B N4B C5B N8B 1.2(3) . . . . ? N3B N4B C5B N1B 0.07(15) . . . . ? C7B N4B C5B N1B -179.46(14) . . . . ? N2B N1B C5B N8B 179.02(13) . . . . ? N6B N1B C5B N8B 3.0(2) . . . . ? N2B N1B C5B N4B -0.35(14) . . . . ? N6B N1B C5B N4B -176.33(12) . . . . ? C13B N9B N10B C11B 0.22(14) . . . . ? N9B N10B C11B N14B 172.94(12) . . . . ? N9B N10B C11B C12B -0.65(15) . . . . ? N10B C11B C12B N17B -179.98(13) . . . . ? N14B C11B C12B N17B 6.8(2) . . . . ? N10B C11B C12B C13B 0.76(14) . . . . ? N14B C11B C12B C13B -172.43(13) . . . . ? N10B N9B C13B N18B -176.78(11) . . . . ? N10B N9B C13B C12B 0.28(15) . . . . ? N17B C12B C13B N9B -179.87(12) . . . . ? C11B C12B C13B N9B -0.62(14) . . . . ? N17B C12B C13B N18B -3.1(2) . . . . ? C11B C12B C13B N18B 176.20(13) . . . . ? N10B C11B N14B O15B 3.15(19) . . . . ? C12B C11B N14B O15B 175.80(12) . . . . ? N10B C11B N14B O16B -175.64(11) . . . . ? C12B C11B N14B O16B -3.00(19) . . . . ? N9B C13B N18B O20B -0.25(18) . . . . ? C12B C13B N18B O20B -176.82(13) . . . . ? N9B C13B N18B O19B 179.06(11) . . . . ? C12B C13B N18B O19B 2.49(19) . . . . ? 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 N6A H6AA N10B 0.919(18) 2.232(18) 3.0263(18) 144.3(15) 2_666 N6A H6AB O20A 0.858(19) 2.23(2) 3.0771(17) 167.1(16) 1_556 N8A H8AA N10A 0.88 2.03 2.8756(17) 160.2 1_546 N17A H17A O16A 0.88 2.32 2.8531(16) 119.4 . N17A H17B O19A 0.88 2.26 2.8143(16) 120.5 . N6B H6BA N9A 0.887(18) 2.105(19) 2.9882(17) 173.7(16) 1_556 N6B H6BB O19B 0.85(2) 2.605(19) 3.2992(17) 139.6(14) . N8B H8BA N9B 0.88 2.00 2.8441(17) 161.2 2_666 N8B H8BB O16A 0.88 2.10 2.9360(16) 159.6 2_666 N17B H17D O16B 0.88 2.28 2.8221(17) 119.6 . N17B H17C O19B 0.88 2.31 2.8522(17) 119.6 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.237 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.050 # Attachment 'shrv140-final.cif' data_shrv140 _database_code_depnum_ccdc_archive 'CCDC 799953' #TrackingRef 'shrv140-final.cif' _audit_creation_date 2010-10-29 _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; Carbonohydrazidium bis-4-amino-3,5-dinitropyrazol-1-ide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C1 H8 N4 O1 2+, 2(C3 H2 N5 O4 1-)' _chemical_formula_sum 'C7 H12 N14 O9' _chemical_formula_weight 436.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 12.571(2) _cell_length_b 9.3810(16) _cell_length_c 13.169(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.658(2) _cell_angle_gamma 90.00 _cell_volume 1539.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9397 _exptl_absorpt_correction_T_max 0.9915 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6893 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 26.45 _reflns_number_total 1576 _reflns_number_gt 1464 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+2.4162P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1576 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.81859(9) 0.46298(12) 0.35458(9) 0.0123(3) Uani 1 1 d . . . N2 N 0.83697(9) 0.33577(12) 0.39624(9) 0.0123(2) Uani 1 1 d . . . C3 C 0.87218(10) 0.35554(14) 0.49812(10) 0.0116(3) Uani 1 1 d . . . C4 C 0.87796(10) 0.50076(14) 0.52578(10) 0.0114(3) Uani 1 1 d . . . C5 C 0.84280(10) 0.56261(14) 0.42995(10) 0.0120(3) Uani 1 1 d . . . N6 N 0.89769(9) 0.24050(12) 0.56444(9) 0.0123(3) Uani 1 1 d . . . O7 O 0.88850(8) 0.11634(10) 0.53345(8) 0.0161(2) Uani 1 1 d . . . O8 O 0.92955(8) 0.27123(11) 0.65650(7) 0.0172(2) Uani 1 1 d . . . N9 N 0.90630(9) 0.56105(13) 0.61765(9) 0.0147(3) Uani 1 1 d . . . H9A H 0.9043 0.6543 0.6241 0.018 Uiso 1 1 calc R . . H9B H 0.9269 0.5073 0.6715 0.018 Uiso 1 1 calc R . . N10 N 0.82966(9) 0.70758(12) 0.40757(9) 0.0125(3) Uani 1 1 d . . . O11 O 0.86016(8) 0.79583(10) 0.47661(8) 0.0159(2) Uani 1 1 d . . . O12 O 0.78849(8) 0.74450(10) 0.32043(8) 0.0163(2) Uani 1 1 d . . . O13 O 1.0000 0.19648(15) 0.2500 0.0174(3) Uani 1 2 d S . . C14 C 1.0000 0.0663(2) 0.2500 0.0116(4) Uani 1 2 d S . . N15 N 0.92279(9) -0.01672(13) 0.28318(10) 0.0165(3) Uani 1 1 d . . . H15 H 0.9284 -0.1102 0.2826 0.020 Uiso 1 1 calc R . . N16 N 0.83366(9) 0.04917(12) 0.31858(9) 0.0122(2) Uani 1 1 d . . . H16A H 0.8249 0.0131 0.3811 0.018 Uiso 1 1 calc R . . H16B H 0.7736 0.0320 0.2736 0.018 Uiso 1 1 calc R . . H16C H 0.8451 0.1448 0.3239 0.018 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0132(5) 0.0113(5) 0.0125(5) 0.0002(4) 0.0020(4) 0.0002(4) N2 0.0126(5) 0.0124(5) 0.0119(5) 0.0008(4) 0.0015(4) 0.0002(4) C3 0.0114(6) 0.0119(6) 0.0115(6) 0.0002(5) 0.0017(5) 0.0004(5) C4 0.0089(6) 0.0128(6) 0.0131(6) -0.0001(5) 0.0031(5) -0.0004(5) C5 0.0122(6) 0.0112(6) 0.0126(6) -0.0003(5) 0.0022(5) -0.0002(5) N6 0.0120(5) 0.0130(6) 0.0120(5) 0.0001(4) 0.0020(4) -0.0005(4) O7 0.0208(5) 0.0106(5) 0.0165(5) -0.0010(4) 0.0007(4) -0.0003(4) O8 0.0245(5) 0.0161(5) 0.0098(5) 0.0001(4) -0.0020(4) -0.0010(4) N9 0.0193(6) 0.0131(6) 0.0113(5) -0.0017(4) 0.0007(5) 0.0000(5) N10 0.0117(5) 0.0117(5) 0.0146(6) 0.0001(4) 0.0032(4) -0.0003(4) O11 0.0198(5) 0.0119(5) 0.0160(5) -0.0040(4) 0.0025(4) -0.0023(4) O12 0.0193(5) 0.0145(5) 0.0143(5) 0.0034(4) -0.0007(4) -0.0006(4) O13 0.0199(7) 0.0107(7) 0.0228(7) 0.000 0.0074(6) 0.000 C14 0.0131(9) 0.0132(9) 0.0078(8) 0.000 -0.0012(7) 0.000 N15 0.0159(6) 0.0104(5) 0.0250(6) -0.0021(5) 0.0090(5) 0.0004(4) N16 0.0126(5) 0.0117(5) 0.0124(5) -0.0008(4) 0.0021(4) 0.0004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.3208(16) . ? N1 C5 1.3678(17) . ? N2 C3 1.3682(17) . ? C3 N6 1.3985(17) . ? C3 C4 1.4095(19) . ? C4 N9 1.3399(17) . ? C4 C5 1.4057(18) . ? C5 N10 1.3966(17) . ? N6 O7 1.2345(15) . ? N6 O8 1.2586(15) . ? N9 H9A 0.8800 . ? N9 H9B 0.8800 . ? N10 O12 1.2435(16) . ? N10 O11 1.2515(15) . ? O13 C14 1.221(2) . ? C14 N15 1.3613(16) . ? C14 N15 1.3613(16) 2_755 ? N15 N16 1.4122(16) . ? N15 H15 0.8800 . ? N16 H16A 0.9100 . ? N16 H16B 0.9100 . ? N16 H16C 0.9100 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C5 107.84(11) . . ? N1 N2 C3 107.49(11) . . ? N2 C3 N6 121.67(12) . . ? N2 C3 C4 112.54(12) . . ? N6 C3 C4 125.79(12) . . ? N9 C4 C5 130.56(13) . . ? N9 C4 C3 129.77(13) . . ? C5 C4 C3 99.65(11) . . ? N1 C5 N10 120.24(12) . . ? N1 C5 C4 112.48(12) . . ? N10 C5 C4 127.27(12) . . ? O7 N6 O8 122.57(11) . . ? O7 N6 C3 121.21(11) . . ? O8 N6 C3 116.22(11) . . ? C4 N9 H9A 120.0 . . ? C4 N9 H9B 120.0 . . ? H9A N9 H9B 120.0 . . ? O12 N10 O11 122.39(11) . . ? O12 N10 C5 119.27(11) . . ? O11 N10 C5 118.34(11) . . ? O13 C14 N15 124.92(8) . . ? O13 C14 N15 124.92(8) . 2_755 ? N15 C14 N15 110.16(17) . 2_755 ? C14 N15 N16 119.10(12) . . ? C14 N15 H15 120.4 . . ? N16 N15 H15 120.4 . . ? N15 N16 H16A 109.5 . . ? N15 N16 H16B 109.5 . . ? H16A N16 H16B 109.5 . . ? N15 N16 H16C 109.5 . . ? H16A N16 H16C 109.5 . . ? H16B N16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 N2 C3 0.36(14) . . . . ? N1 N2 C3 N6 179.30(11) . . . . ? N1 N2 C3 C4 -0.19(15) . . . . ? N2 C3 C4 N9 178.45(13) . . . . ? N6 C3 C4 N9 -1.0(2) . . . . ? N2 C3 C4 C5 -0.07(14) . . . . ? N6 C3 C4 C5 -179.53(13) . . . . ? N2 N1 C5 N10 -179.33(11) . . . . ? N2 N1 C5 C4 -0.43(15) . . . . ? N9 C4 C5 N1 -178.21(13) . . . . ? C3 C4 C5 N1 0.30(14) . . . . ? N9 C4 C5 N10 0.6(2) . . . . ? C3 C4 C5 N10 179.09(13) . . . . ? N2 C3 N6 O7 -0.59(19) . . . . ? C4 C3 N6 O7 178.83(12) . . . . ? N2 C3 N6 O8 179.81(12) . . . . ? C4 C3 N6 O8 -0.77(19) . . . . ? N1 C5 N10 O12 5.19(19) . . . . ? C4 C5 N10 O12 -173.52(12) . . . . ? N1 C5 N10 O11 -174.75(11) . . . . ? C4 C5 N10 O11 6.5(2) . . . . ? O13 C14 N15 N16 1.53(13) . . . . ? N15 C14 N15 N16 -178.47(13) 2_755 . . . ? 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 N9 H9A O11 0.88 2.36 2.8896(16) 119.1 . N9 H9B O8 0.88 2.22 2.7747(16) 120.3 . N9 H9B O8 0.88 2.22 2.7747(16) 120.3 . N15 H15 O8 0.88 2.25 2.9203(16) 133.3 6 N16 H16A O7 0.91 2.27 2.8911(16) 124.7 . N16 H16B N1 0.91 2.02 2.8902(16) 159.0 4_645 N16 H16C N2 0.91 2.04 2.8748(17) 152.4 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.497 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.061