# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'J. M. Shreeve' 'Haixiang Gao' 'M. Hiskey' 'Brendan Twamley' 'Ruihu Wang.' _publ_contact_author_name 'J. M. Shreeve' _publ_contact_author_address ; Department of Chemistry University of Idaho Moscow ID 83844-2343 UNITED STATES OF AMERICA ; _publ_contact_author_email JSHREEVE@UIDAHO.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; 3-Amino-6-nitroamino-tetrazine (ANAT)-Based Energetic Salts ; data_bt847 _database_code_depnum_ccdc_archive 'CCDC 610552' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'C2 H2 N7 O2, C H6 N3' _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 N7 O2, C H6 N3' _chemical_formula_sum 'C3 H8 N10 O2' _chemical_formula_weight 216.19 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.155(2) _cell_length_b 15.305(4) _cell_length_c 6.8667(18) _cell_angle_alpha 90.00 _cell_angle_beta 99.895(5) _cell_angle_gamma 90.00 _cell_volume 844.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 89(2) _cell_measurement_reflns_used 6297 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 30.04 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9721 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details 'SADABS; Bruker, 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 89(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 scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12622 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1530 _reflns_number_gt 1446 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v. 5.630' _computing_cell_refinement 'Bruker SAINT+ v. 6.45a' _computing_data_reduction 'Bruker SAINT+ v. 6.45a' _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^)+(0.0309P)^2^+0.5414P] 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 1530 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 N2 N 0.59703(16) 0.81540(8) 0.52969(19) 0.0186(3) Uani 1 1 d . . . H2A H 0.4986 0.7923 0.4874 0.022 Uiso 1 1 calc R . . H2B H 0.6683 0.7885 0.6208 0.022 Uiso 1 1 calc R . . N3 N 0.78628(15) 0.92711(8) 0.52027(18) 0.0176(3) Uani 1 1 d . . . H3A H 0.8120 0.9775 0.4715 0.021 Uiso 1 1 calc R . . H3B H 0.8584 0.9007 0.6114 0.021 Uiso 1 1 calc R . . N4 N 0.53130(16) 0.93122(8) 0.31949(18) 0.0186(3) Uani 1 1 d . . . H4A H 0.4328 0.9081 0.2771 0.022 Uiso 1 1 calc R . . H4B H 0.5586 0.9813 0.2707 0.022 Uiso 1 1 calc R . . O2 O 0.17745(13) 0.89665(7) 0.66311(16) 0.0214(3) Uani 1 1 d . . . O1 O 0.41168(13) 0.90813(7) 0.87138(15) 0.0189(3) Uani 1 1 d . . . C1 C 0.63796(18) 0.89082(10) 0.4560(2) 0.0154(3) Uani 1 1 d . . . C7 C 0.15643(18) 0.73009(9) 0.7534(2) 0.0141(3) Uani 1 1 d . . . C10 C -0.08361(18) 0.62758(9) 0.6031(2) 0.0143(3) Uani 1 1 d . . . N5 N 0.29133(15) 0.86224(8) 0.78687(18) 0.0157(3) Uani 1 1 d . . . N6 N 0.29555(15) 0.77917(8) 0.83246(18) 0.0160(3) Uani 1 1 d . . . N8 N 0.19435(15) 0.64767(8) 0.70887(17) 0.0153(3) Uani 1 1 d . . . N9 N 0.07329(15) 0.59475(8) 0.63330(18) 0.0153(3) Uani 1 1 d . . . N11 N -0.12238(15) 0.70454(8) 0.68005(18) 0.0160(3) Uani 1 1 d . . . N12 N 0.00067(16) 0.75736(8) 0.75464(19) 0.0157(3) Uani 1 1 d . . . N13 N -0.20447(15) 0.57929(8) 0.50161(18) 0.0177(3) Uani 1 1 d . . . H13A H -0.3082 0.5976 0.4853 0.021 Uiso 1 1 calc R . . H13B H -0.1807 0.5290 0.4508 0.021 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 N2 0.0143(6) 0.0192(7) 0.0210(7) 0.0039(5) -0.0005(5) -0.0003(5) N3 0.0170(6) 0.0169(6) 0.0178(6) 0.0020(5) -0.0007(5) -0.0015(5) N4 0.0152(6) 0.0178(7) 0.0215(7) 0.0035(5) -0.0004(5) -0.0030(5) O2 0.0205(6) 0.0184(6) 0.0230(6) 0.0050(4) -0.0032(5) -0.0010(4) O1 0.0180(5) 0.0165(5) 0.0211(6) -0.0026(4) 0.0000(4) -0.0046(4) C1 0.0164(7) 0.0170(8) 0.0139(7) -0.0036(6) 0.0053(6) 0.0010(6) C7 0.0165(7) 0.0151(7) 0.0111(7) 0.0012(6) 0.0033(6) 0.0016(6) C10 0.0164(7) 0.0136(7) 0.0137(7) 0.0035(5) 0.0050(6) -0.0003(6) N5 0.0155(6) 0.0160(6) 0.0157(6) -0.0012(5) 0.0033(5) -0.0006(5) N6 0.0163(6) 0.0127(6) 0.0189(6) -0.0008(5) 0.0024(5) -0.0006(5) N8 0.0163(6) 0.0147(6) 0.0152(6) 0.0003(5) 0.0033(5) -0.0005(5) N9 0.0164(6) 0.0140(6) 0.0155(6) 0.0000(5) 0.0030(5) -0.0007(5) N11 0.0155(6) 0.0149(6) 0.0179(6) 0.0014(5) 0.0039(5) -0.0003(5) N12 0.0162(6) 0.0145(6) 0.0168(6) -0.0001(5) 0.0040(5) -0.0010(5) N13 0.0145(6) 0.0154(6) 0.0229(7) -0.0033(5) 0.0029(5) 0.0003(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 N2 C1 1.326(2) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 C1 1.335(2) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N4 C1 1.318(2) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? O2 N5 1.2613(16) . ? O1 N5 1.2639(16) . ? C7 N12 1.338(2) . ? C7 N8 1.3463(19) . ? C7 N6 1.3909(19) . ? C10 N13 1.3292(19) . ? C10 N11 1.3506(19) . ? C10 N9 1.3570(19) . ? N5 N6 1.3084(18) . ? N8 N9 1.3130(17) . ? N11 N12 1.3215(18) . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? 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 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C1 N4 H4A 120.0 . . ? C1 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? N4 C1 N2 120.08(14) . . ? N4 C1 N3 119.31(14) . . ? N2 C1 N3 120.61(14) . . ? N12 C7 N8 123.29(13) . . ? N12 C7 N6 122.72(13) . . ? N8 C7 N6 113.01(12) . . ? N13 C10 N11 119.19(13) . . ? N13 C10 N9 117.97(13) . . ? N11 C10 N9 122.75(13) . . ? O2 N5 O1 120.08(12) . . ? O2 N5 N6 123.57(12) . . ? O1 N5 N6 116.34(12) . . ? N5 N6 C7 116.45(12) . . ? N9 N8 C7 118.77(12) . . ? N8 N9 C10 117.21(12) . . ? N12 N11 C10 118.16(12) . . ? N11 N12 C7 117.72(12) . . ? C10 N13 H13A 120.0 . . ? C10 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A N6 0.88 2.11 2.9715(18) 165.0 4_575 N2 H2B N11 0.88 2.12 2.8930(18) 146.3 1_655 N3 H3A O2 0.88 2.14 3.0128(18) 168.7 3_676 N3 H3B O2 0.88 2.57 3.2063(18) 130.3 1_655 N3 H3B N12 0.88 2.59 3.3807(19) 149.2 1_655 N4 H4A N8 0.88 2.10 2.9780(19) 173.7 4_575 N4 H4B O1 0.88 1.99 2.8616(17) 171.0 3_676 N13 H13A O1 0.88 2.29 3.1103(18) 156.1 4_475 N13 H13B N9 0.88 2.21 3.0722(19) 168.3 3_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.274 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.042