# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'J. M. Shreeve' 'Brendan Twamley' 'Ji-Chang Xiao.' 'Chengfeng Ye.' _publ_contact_author_name 'Prof J M Shreeve' _publ_contact_author_address ; Department of Chemistry University of Idaho Moscow ID 83844-2343 USA ; _publ_contact_author_email JSHREEVE@UIDAHO.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Energetic salts of azotetrazolate, iminobis(5-tetrazolate) and 5, 5'-bis(tetrazolate) ; data_bt656 _database_code_depnum_ccdc_archive 'CCDC 265160' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N18' _chemical_formula_weight 362.37 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Ibam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1, y+1, -z+1/2' 'x+1, -y+1, -z+1/2' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'x, -y, z+1/2' '-x, y, z+1/2' _cell_length_a 10.4301(13) _cell_length_b 23.494(3) _cell_length_c 6.0885(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1491.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 86(2) _cell_measurement_reflns_used 1324 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 24.39 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9564 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details 'SADABS (SAINT+, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 86(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker/Siemens SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <0.01 _diffrn_reflns_number 8310 _diffrn_reflns_av_R_equivalents 0.0860 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.35 _reflns_number_total 754 _reflns_number_gt 557 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v. 5.626' _computing_cell_refinement 'Bruker SAINT+ v. 6.36a' _computing_data_reduction 'Bruker SAINT+ v. 6.36a' _computing_structure_solution 'XS, Bruker SHELXTL v. 6.12' _computing_structure_refinement 'XL, Bruker SHELXTL v. 6.12' _computing_molecular_graphics 'XP, Bruker SHELXTL v. 6.12' _computing_publication_material 'XCIF, Bruker SHELXTL v. 6.12' _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^)+(0.0533P)^2^+2.7380P] 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 754 _refine_ls_number_parameters 94 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.043 _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 0.2485(3) 0.05335(12) 0.0000 0.0244(7) Uani 1 2 d S . . N2 N 0.2759(3) 0.10925(13) 0.0000 0.0266(8) Uani 1 2 d S . . N3 N 0.1673(3) 0.13859(13) 0.0000 0.0308(8) Uani 1 2 d S . . N4 N 0.0680(3) 0.10310(12) 0.0000 0.0265(8) Uani 1 2 d S . . C5 C 0.1201(3) 0.05181(14) 0.0000 0.0186(8) Uani 1 2 d S . . N6 N 0.0599(3) -0.00185(13) 0.0000 0.0234(7) Uani 1 2 d SU . . N7 N 0.4152(4) 0.04964(14) 0.5000 0.0341(9) Uani 1 2 d S . . H7A H 0.343(5) 0.0273(19) 0.555(9) 0.041 Uiso 0.50 1 d P A -1 H7B H 0.453(5) 0.046(2) 0.369(9) 0.041 Uiso 0.50 1 d P B -1 N8 N 0.3614(3) 0.10465(12) 0.5000 0.0232(7) Uani 1 2 d S . . C9 C 0.4330(4) 0.15240(17) 0.5000 0.0338(10) Uani 1 2 d S . . H9 H 0.523(4) 0.1520(16) 0.5000 0.041 Uiso 1 2 d S . . N10 N 0.3615(3) 0.19717(14) 0.5000 0.0439(10) Uani 1 2 d S . . N11 N 0.2387(3) 0.17638(13) 0.5000 0.0301(8) Uani 1 2 d S . . C12 C 0.2385(3) 0.12103(16) 0.5000 0.0223(8) Uani 1 2 d S . . H12 H 0.169(4) 0.0991(15) 0.5000 0.027 Uiso 1 2 d S . . C13 C 0.1288(4) 0.21474(19) 0.5000 0.0468(13) Uani 1 2 d S . . H13A H 0.055(4) 0.1965(19) 0.5000 0.056 Uiso 1 2 d S . . H13B H 0.129(3) 0.2368(12) 0.377(6) 0.056 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 0.0190(16) 0.0341(17) 0.0201(16) 0.000 0.000 0.0033(14) N2 0.0207(16) 0.038(2) 0.0209(17) 0.000 0.000 -0.0072(14) N3 0.0303(18) 0.0305(18) 0.0316(19) 0.000 0.000 0.0006(14) N4 0.0198(17) 0.0305(17) 0.0292(18) 0.000 0.000 -0.0015(14) C5 0.0158(18) 0.0269(19) 0.0132(17) 0.000 0.000 -0.0010(15) N6 0.0221(10) 0.0283(11) 0.0198(10) 0.000 0.000 0.0019(9) N7 0.029(2) 0.0266(19) 0.047(2) 0.000 0.000 0.0054(15) N8 0.0211(15) 0.0259(16) 0.0226(17) 0.000 0.000 -0.0036(14) C9 0.020(2) 0.029(2) 0.053(3) 0.000 0.000 -0.0019(18) N10 0.0226(18) 0.0268(18) 0.082(3) 0.000 0.000 -0.0070(15) N11 0.0191(16) 0.0256(18) 0.045(2) 0.000 0.000 0.0004(14) C12 0.0190(19) 0.029(2) 0.0192(19) 0.000 0.000 -0.0056(16) C13 0.029(2) 0.028(2) 0.083(4) 0.000 0.000 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.339(4) . ? N1 N2 1.344(4) . ? N2 N3 1.326(4) . ? N3 N4 1.329(4) . ? N4 C5 1.322(4) . ? C5 N6 1.409(4) . ? N6 N6 1.253(5) 9 ? N7 N8 1.409(4) . ? N7 H7A 0.97(5) . ? N7 H7B 0.90(5) . ? N8 C12 1.339(5) . ? N8 C9 1.348(5) . ? C9 N10 1.290(5) . ? C9 H9 0.94(4) . ? N10 N11 1.371(4) . ? N11 C12 1.300(5) . ? N11 C13 1.458(5) . ? C12 H12 0.89(4) . ? C13 H13A 0.88(4) . ? C13 H13B 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 C5 N1 N2 103.8(3) . . ? N3 N2 N1 109.0(3) . . ? N2 N3 N4 109.8(3) . . ? C5 N4 N3 104.6(3) . . ? N4 C5 N1 112.7(3) . . ? N4 C5 N6 129.2(3) . . ? N1 C5 N6 118.0(3) . . ? N6 N6 C5 112.5(4) 9 . ? N8 N7 H7A 101(3) . . ? N8 N7 H7B 106(3) . . ? H7A N7 H7B 126(5) . . ? C12 N8 C9 107.0(3) . . ? C12 N8 N7 130.1(3) . . ? C9 N8 N7 122.9(3) . . ? N10 C9 N8 111.0(3) . . ? N10 C9 H9 126(2) . . ? N8 C9 H9 123(2) . . ? C9 N10 N11 104.5(3) . . ? C12 N11 N10 111.0(3) . . ? C12 N11 C13 128.1(3) . . ? N10 N11 C13 120.9(3) . . ? N11 C12 N8 106.6(3) . . ? N11 C12 H12 125(2) . . ? N8 C12 H12 128(2) . . ? N11 C13 H13A 113(3) . . ? N11 C13 H13B 110(2) . . ? H13A C13 H13B 106(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 N7 H7A N1 0.97(5) 2.16(5) 2.979(5) 140(4) 8_445 N7 H7A N1 0.97(5) 2.16(5) 2.979(5) 140(4) 15 C9 H9 N2 0.94(4) 2.33(4) 3.201(5) 155(3) 7_545 C9 H9 N2 0.94(4) 2.33(4) 3.201(5) 155(3) 16_655 C12 H12 N6 0.89(4) 2.55(4) 3.363(5) 152(3) 8_445 C12 H12 N4 0.89(4) 2.47(4) 3.224(5) 142(3) 7_445 C12 H12 N4 0.89(4) 2.47(4) 3.224(5) 142(3) 16 C12 H12 N6 0.89(4) 2.55(4) 3.363(5) 152(3) 15 C13 H13A N4 0.88(4) 2.54(5) 3.331(6) 149(4) 7_445 C13 H13A N4 0.88(4) 2.54(5) 3.331(6) 149(4) 16 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.483 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.052