# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2008


data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

_publ_contact_author_name        'J M Shreeve'
_publ_contact_author_email       JSHREEVE@UIDAHO.EDU

_publ_section_title              
;
Energetic Nitrogen-Rich Salts and Ionic Liquids:
5-Aminotetrazole (AT) as a Weak Acid
;
loop_
_publ_author_name
'J M Shreeve'
'Yong Guo.'
'Young-Hyuk Joo.'
'Guo-Hong Tao.'
'Brendan Twamley'

# Attachment 'Guo-Hong_-_ATM_-_CIF_-_07-05-08.txt'

data_bt1279
_database_code_depnum_ccdc_archive 'CCDC 690394'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'C2H8N5, CH2N5'
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H8 N5, C H2 N5'
_chemical_formula_sum            'C3 H10 N10'
_chemical_formula_weight         186.21

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.6667(6)
_cell_length_b                   9.4916(11)
_cell_length_c                   15.9768(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     859.33(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9067
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      29.94

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'SADABS-2007/4 (Bruker, 2007)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12696
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         28.98
_reflns_number_total             1343
_reflns_number_gt                1313
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART v. 5.632 (Bruker, 2006)'
_computing_cell_refinement       'SAINT+ v. 7.23a (Bruker, 2006)'
_computing_data_reduction        'SAINT+ v. 7.23a (Bruker, 2006)'
_computing_structure_solution    'XS, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_structure_refinement  'XL, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_publication_material  'XCIF, SHELXTL, v. 6.14 (Bruker, 2003)'

_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^)+(0.0471P)^2^+0.1743P] 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    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_number_reflns         1343
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C3 C 0.7915(2) 0.52984(14) 0.43761(8) 0.0146(3) Uani 1 1 d . . .
C5 C 0.5176(2) 0.45884(14) 0.33619(8) 0.0159(3) Uani 1 1 d . . .
C9 C 0.0450(2) 0.61577(13) 0.17249(8) 0.0142(3) Uani 1 1 d . . .
N1 N 0.7941(2) 0.40792(13) 0.48063(7) 0.0166(2) Uani 1 1 d . . .
H1A H 0.764(4) 0.329(2) 0.4550(12) 0.027(5) Uiso 1 1 d . . .
H1B H 0.869(4) 0.406(2) 0.5251(13) 0.029(5) Uiso 1 1 d . . .
N2 N 0.9012(2) 0.64079(13) 0.47066(8) 0.0175(2) Uani 1 1 d . . .
H2A H 1.000(4) 0.626(2) 0.5136(12) 0.022(5) Uiso 1 1 d . . .
H2B H 0.907(4) 0.720(2) 0.4427(12) 0.025(5) Uiso 1 1 d . . .
N4 N 0.6926(2) 0.54392(12) 0.36190(7) 0.0167(2) Uani 1 1 d . . .
N6 N 0.3442(2) 0.41143(14) 0.38536(8) 0.0194(3) Uani 1 1 d . . .
H6A H 0.335(3) 0.440(2) 0.4368(13) 0.024(5) Uiso 1 1 d . . .
H6B H 0.242(4) 0.352(2) 0.3640(13) 0.035(6) Uiso 1 1 d . . .
N7 N 0.5098(2) 0.42671(14) 0.25474(8) 0.0193(3) Uani 1 1 d . . .
H7A H 0.637(4) 0.451(2) 0.2236(13) 0.028(5) Uiso 1 1 d . . .
H7B H 0.395(4) 0.378(2) 0.2347(13) 0.031(5) Uiso 1 1 d . . .
N8 N -0.0455(2) 0.71596(12) 0.22686(8) 0.0173(2) Uani 1 1 d . . .
H8A H 0.067(4) 0.778(2) 0.2414(12) 0.034(6) Uiso 1 1 d . . .
H8B H -0.114(4) 0.678(2) 0.2680(13) 0.032(6) Uiso 1 1 d . . .
N10 N -0.0373(2) 0.48354(12) 0.16895(7) 0.0154(2) Uani 1 1 d . . .
N11 N 0.0894(2) 0.42292(12) 0.10693(7) 0.0171(2) Uani 1 1 d . . .
N12 N 0.2371(2) 0.51500(13) 0.07543(7) 0.0182(3) Uani 1 1 d . . .
N13 N 0.2134(2) 0.64049(12) 0.11570(7) 0.0171(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
C3 0.0129(5) 0.0160(6) 0.0151(5) -0.0009(5) 0.0017(5) 0.0013(5)
C5 0.0160(6) 0.0155(5) 0.0161(6) 0.0005(5) -0.0016(5) 0.0018(5)
C9 0.0146(6) 0.0139(5) 0.0140(5) 0.0015(4) -0.0023(5) 0.0011(5)
N1 0.0200(6) 0.0142(5) 0.0158(5) 0.0000(4) -0.0028(5) -0.0009(5)
N2 0.0207(6) 0.0147(5) 0.0170(5) 0.0014(4) -0.0043(5) -0.0008(5)
N4 0.0168(5) 0.0188(5) 0.0146(5) 0.0015(4) -0.0017(5) -0.0024(5)
N6 0.0165(5) 0.0243(6) 0.0175(5) -0.0038(5) 0.0007(4) -0.0043(5)
N7 0.0168(5) 0.0256(6) 0.0156(5) -0.0010(5) -0.0014(4) -0.0041(5)
N8 0.0206(6) 0.0139(5) 0.0175(5) -0.0022(4) 0.0023(5) 0.0005(5)
N10 0.0170(5) 0.0140(5) 0.0152(5) -0.0010(4) 0.0015(4) 0.0005(5)
N11 0.0200(5) 0.0161(5) 0.0151(5) -0.0010(4) 0.0016(4) 0.0017(5)
N12 0.0201(6) 0.0172(5) 0.0174(5) -0.0001(4) 0.0022(4) 0.0014(5)
N13 0.0192(5) 0.0162(5) 0.0161(5) 0.0005(4) 0.0010(5) -0.0006(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
C3 N2 1.3320(18) . ?
C3 N4 1.3399(17) . ?
C3 N1 1.3459(18) . ?
C5 N6 1.3360(18) . ?
C5 N7 1.3373(18) . ?
C5 N4 1.3432(18) . ?
C9 N13 1.3374(18) . ?
C9 N10 1.3403(17) . ?
C9 N8 1.3865(17) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.83(2) . ?
N2 H2A 0.90(2) . ?
N2 H2B 0.87(2) . ?
N6 H6A 0.87(2) . ?
N6 H6B 0.88(2) . ?
N7 H7A 0.91(2) . ?
N7 H7B 0.86(2) . ?
N8 H8A 0.90(2) . ?
N8 H8B 0.84(2) . ?
N10 N11 1.3523(16) . ?
N11 N12 1.3107(17) . ?
N12 N13 1.3605(17) . ?

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 C3 N4 118.31(13) . . ?
N2 C3 N1 118.18(12) . . ?
N4 C3 N1 123.46(13) . . ?
N6 C5 N7 118.10(13) . . ?
N6 C5 N4 124.45(13) . . ?
N7 C5 N4 117.32(13) . . ?
N13 C9 N10 112.59(12) . . ?
N13 C9 N8 124.66(12) . . ?
N10 C9 N8 122.67(13) . . ?
C3 N1 H1A 119.7(13) . . ?
C3 N1 H1B 117.8(15) . . ?
H1A N1 H1B 118.9(19) . . ?
C3 N2 H2A 117.9(12) . . ?
C3 N2 H2B 119.6(13) . . ?
H2A N2 H2B 120.3(18) . . ?
C3 N4 C5 121.66(12) . . ?
C5 N6 H6A 119.9(14) . . ?
C5 N6 H6B 118.2(14) . . ?
H6A N6 H6B 122(2) . . ?
C5 N7 H7A 116.7(13) . . ?
C5 N7 H7B 120.7(15) . . ?
H7A N7 H7B 122.3(17) . . ?
C9 N8 H8A 110.3(14) . . ?
C9 N8 H8B 111.3(14) . . ?
H8A N8 H8B 114(2) . . ?
C9 N10 N11 104.15(11) . . ?
N12 N11 N10 109.68(11) . . ?
N11 N12 N13 109.83(11) . . ?
C9 N13 N12 103.75(11) . . ?

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 H1A N13 0.87(2) 2.12(2) 2.9687(17) 165(2) 3_645
N1 H1B N12 0.83(2) 2.49(2) 3.1442(18) 136.7(18) 2_665
N2 H2A N12 0.90(2) 2.23(2) 3.0313(17) 148.4(16) 2_665
N2 H2B N11 0.87(2) 2.08(2) 2.9513(17) 171.5(17) 3_655
N6 H6A N12 0.87(2) 2.29(2) 3.1498(17) 170.3(18) 2_565
N6 H6B N8 0.88(2) 2.24(2) 3.0858(18) 162.0(19) 3_545
N7 H7A N10 0.91(2) 2.06(2) 2.9590(18) 169.0(18) 1_655
N7 H7B N8 0.86(2) 2.58(2) 3.3181(19) 144.4(18) 3_545
N8 H8A N10 0.90(2) 2.43(2) 3.0726(17) 128.9(18) 3
N8 H8B N4 0.84(2) 2.25(2) 3.0860(17) 169.8(19) 1_455

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.98
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.041