#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:51:45 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233355 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/58/7235815.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7235815
loop_
_publ_author_name
'Klapötke, Thomas M.'
'Schmid, Philipp. C.'
'Schnell, Simon'
'Stierstorfer, Jörg'
_publ_section_title
;
 Thermal stabilization of energetic materials by the aromatic
 nitrogen-rich
 4,4′,5,5′-tetraamino-3,3′-bi-1,2,4-triazolium cation
;
_journal_issue                   6
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              2658
_journal_paper_doi               10.1039/C4TA05964F
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety
'C4 H8 N10, C4 H10 N10, 2(C H N6 O2), 4(H2 O)'
_chemical_formula_sum            'C10 H28 N32 O8'
_chemical_formula_weight         724.64
_chemical_name_common
;
5,5-bis(3,4-diaminotriazolium) 5-nitrimino-1H-tetrazolate
 5,5-bis(3,4-diaminotriazole) hydrate
;
_chemical_name_systematic
;
5,5-bis(3,4-diaminotriazolium) 5-nitrimino-1H-tetrazolate
 5,5-bis(3,4-diaminotriazole) hydrate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Thu Jul 10 16:04:57 2014'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_update_record
;
2014-10-14 deposited with the CCDC.
2014-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                109.650(7)
_cell_angle_beta                 96.080(6)
_cell_angle_gamma                116.486(8)
_cell_formula_units_Z            1
_cell_length_a                   9.2750(7)
_cell_length_b                   9.5253(8)
_cell_length_c                   9.8392(8)
_cell_measurement_reflns_used    2273
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.1710
_cell_measurement_theta_min      4.5420
_cell_volume                     698.14(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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).
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0033257000
_diffrn_orient_matrix_UB_12      -0.0623167000
_diffrn_orient_matrix_UB_13      0.0256559000
_diffrn_orient_matrix_UB_21      -0.0794689000
_diffrn_orient_matrix_UB_22      -0.0634973000
_diffrn_orient_matrix_UB_23      -0.0556611000
_diffrn_orient_matrix_UB_31      0.0414132000
_diffrn_orient_matrix_UB_32      -0.0241831000
_diffrn_orient_matrix_UB_33      -0.0519401000
_diffrn_radiation_collimation    0.5
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5502
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         4.20
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.9500
_exptl_absorpt_correction_T_min  0.9300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0447P)²+0.1560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                2371
_reflns_number_total             2872
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ta05964f2.cif
_cod_data_source_block           jx226
_cod_database_code               7235815
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N8 N 0.17755(14) 0.61323(15) 0.30003(13) 0.0173(3) Uani 1 1 d
N7 N 0.04341(14) 0.58883(15) 0.36074(13) 0.0178(3) Uani 1 1 d
N9 N 0.19583(14) 0.50492(15) 0.46158(13) 0.0158(3) Uani 1 1 d
N10 N 0.41259(15) 0.57316(17) 0.34393(15) 0.0202(3) Uani 1 1 d
N11 N 0.26168(16) 0.44186(19) 0.54655(16) 0.0205(3) Uani 1 1 d
C2 C 0.26639(17) 0.56200(17) 0.36284(15) 0.0156(3) Uani 1 1 d
C5 C 0.05682(17) 0.52399(17) 0.45593(15) 0.0160(3) Uani 1 1 d
C3 C 0.36353(17) 0.09937(17) 0.29633(15) 0.0167(3) Uani 1 1 d
N12 N 0.50635(15) 0.11299(16) 0.26899(14) 0.0187(3) Uani 1 1 d
C4 C 0.48465(17) 0.02628(18) 0.44143(15) 0.0170(3) Uani 1 1 d
N16 N 0.20966(16) 0.0151(2) 0.46379(16) 0.0228(3) Uani 1 1 d
N15 N 0.26093(16) 0.13645(17) 0.23495(15) 0.0206(3) Uani 1 1 d
N14 N 0.34574(14) 0.04083(15) 0.40473(13) 0.0165(3) Uani 1 1 d
N13 N 0.58393(15) 0.06771(16) 0.36034(14) 0.0198(3) Uani 1 1 d
O1 O 0.44282(14) 0.28274(17) 0.04278(14) 0.0338(3) Uani 1 1 d
O2 O 0.60519(14) 0.33122(16) -0.09921(13) 0.0318(3) Uani 1 1 d
N1 N 0.86596(14) 0.29739(15) -0.06794(14) 0.0180(3) Uani 1 1 d
N2 N 1.00339(15) 0.28030(16) -0.06228(14) 0.0211(3) Uani 1 1 d
N3 N 1.01644(16) 0.22663(16) 0.04086(14) 0.0233(3) Uani 1 1 d
N4 N 0.88984(15) 0.20712(16) 0.10346(14) 0.0223(3) Uani 1 1 d
N5 N 0.65960(15) 0.24763(17) 0.07813(14) 0.0219(3) Uani 1 1 d
N6 N 0.56931(15) 0.28851(16) 0.00385(14) 0.0222(3) Uani 1 1 d
C1 C 0.79795(17) 0.25266(18) 0.03546(16) 0.0177(3) Uani 1 1 d
O3 O 0.96672(14) 0.09840(17) 0.31391(13) 0.0258(3) Uani 1 1 d
O4 O 0.75223(16) 0.72408(16) 0.22265(14) 0.0307(3) Uani 1 1 d
H20B H 0.266(2) 0.495(2) 0.641(2) 0.029(5) Uiso 1 1 d
H16B H 0.433(2) 0.584(2) 0.262(2) 0.031(5) Uiso 1 1 d
H13B H 0.287(2) 0.172(2) 0.164(2) 0.029(5) Uiso 1 1 d
H12B H 0.249(2) 0.093(2) 0.558(2) 0.032(5) Uiso 1 1 d
H20A H 0.183(2) 0.327(3) 0.512(2) 0.036(5) Uiso 1 1 d
H13A H 0.168(2) 0.118(2) 0.262(2) 0.030(5) Uiso 1 1 d
H12A H 0.164(2) -0.093(3) 0.462(2) 0.033(5) Uiso 1 1 d
H16A H 0.451(2) 0.518(2) 0.380(2) 0.030(5) Uiso 1 1 d
H3B H 0.918(3) 0.122(3) 0.249(3) 0.050(6) Uiso 1 1 d
H4A H 0.826(3) 0.706(3) 0.186(3) 0.052(6) Uiso 1 1 d
H3A H 0.911(3) -0.008(3) 0.290(3) 0.056(7) Uiso 1 1 d
H4B H 0.684(3) 0.703(3) 0.143(3) 0.061(7) Uiso 1 1 d
H12 H 0.558(2) 0.155(2) 0.203(2) 0.025(4) Uiso 1 1 d
H1 H 0.830(3) 0.333(3) -0.144(2) 0.051(6) Uiso 1 1 d
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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
C2 N8 N7 107.38(11) .
C5 N7 N8 106.92(11) .
C2 N9 C5 105.21(11) .
C2 N9 N11 123.50(11) .
C5 N9 N11 131.29(11) .
C2 N10 H16B 115.0(12) .
C2 N10 H16A 118.5(11) .
H16B N10 H16A 118.8(16) .
N9 N11 H20B 106.6(11) .
N9 N11 H20A 106.0(12) .
H20B N11 H20A 107.9(16) .
N8 C2 N10 127.23(13) .
N8 C2 N9 110.01(12) .
N10 C2 N9 122.62(13) .
N7 C5 N9 110.48(11) .
N7 C5 C5 126.08(15) 2_566
N9 C5 C5 123.43(15) 2_566
N15 C3 N12 128.46(13) .
N15 C3 N14 125.83(13) .
N12 C3 N14 105.71(12) .
C3 N12 N13 111.73(11) .
C3 N12 H12 127.9(10) .
N13 N12 H12 120.2(10) .
N13 C4 N14 111.71(12) .
N13 C4 C4 124.81(16) 2_656
N14 C4 C4 123.47(15) 2_656
N14 N16 H12B 108.7(12) .
N14 N16 H12A 107.0(11) .
H12B N16 H12A 109.0(17) .
C3 N15 H13B 116.2(11) .
C3 N15 H13A 118.6(11) .
H13B N15 H13A 125.0(16) .
C3 N14 C4 106.76(11) .
C3 N14 N16 121.18(11) .
C4 N14 N16 131.96(11) .
C4 N13 N12 104.07(11) .
C1 N1 N2 107.68(11) .
C1 N1 H1 131.9(11) .
N2 N1 H1 120.4(11) .
N3 N2 N1 107.26(11) .
N2 N3 N4 110.27(11) .
C1 N4 N3 106.34(11) .
N6 N5 C1 117.01(11) .
O2 N6 O1 120.56(12) .
O2 N6 N5 122.76(12) .
O1 N6 N5 116.68(11) .
N4 C1 N1 108.46(12) .
N4 C1 N5 119.34(12) .
N1 C1 N5 132.21(13) .
H3B O3 H3A 109(2) .
H4A O4 H4B 100(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N8 C2 1.3238(18) .
N8 N7 1.3970(15) .
N7 C5 1.3065(17) .
N9 C2 1.3566(17) .
N9 C5 1.3781(17) .
N9 N11 1.4105(15) .
N10 C2 1.3501(18) .
N10 H16B 0.874(19) .
N10 H16A 0.887(18) .
N11 H20B 0.89(2) .
N11 H20A 0.91(2) .
C5 C5 1.450(3) 2_566
C3 N15 1.3101(19) .
C3 N12 1.3377(18) .
C3 N14 1.3532(17) .
N12 N13 1.3828(16) .
N12 H12 0.940(17) .
C4 N13 1.2975(18) .
C4 N14 1.3797(18) .
C4 C4 1.451(3) 2_656
N16 N14 1.4022(16) .
N16 H12B 0.88(2) .
N16 H12A 0.910(19) .
N15 H13B 0.883(18) .
N15 H13A 0.889(19) .
O1 N6 1.2562(15) .
O2 N6 1.2380(15) .
N1 C1 1.3425(18) .
N1 N2 1.3530(17) .
N1 H1 1.01(2) .
N2 N3 1.2977(17) .
N3 N4 1.3521(17) .
N4 C1 1.3290(19) .
N5 N6 1.3190(17) .
N5 C1 1.3776(18) .
O3 H3B 0.89(2) .
O3 H3A 0.83(2) .
O4 H4A 0.86(2) .
O4 H4B 0.86(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
N10 H16B O2 0.874(19) 2.087(19) 2.8599(17) 147.1(16) 2_665
N15 H13B O1 0.883(18) 2.117(18) 2.9519(17) 157.4(16) .
N16 H12B O4 0.88(2) 2.27(2) 3.106(2) 158.0(16) 2_666
N11 H20A O3 0.91(2) 2.23(2) 3.013(2) 143.6(16) 1_455
N15 H13A O3 0.889(19) 1.933(19) 2.8174(17) 173.0(16) 1_455
N16 H12A N7 0.910(19) 2.48(2) 3.3476(19) 159.3(16) 1_545
N16 H12A O3 0.910(19) 2.634(18) 3.0659(16) 109.9(13) 2_656
N10 H16A N11 0.887(18) 2.505(18) 3.1795(18) 133.2(14) 2_666
O3 H3B N4 0.89(2) 1.91(2) 2.7671(17) 160.4(19) .
O3 H3B N3 0.89(2) 2.64(2) 3.2999(16) 131.9(17) .
O4 H4A N2 0.86(2) 2.08(2) 2.9029(17) 159(2) 2_765
O3 H3A O4 0.83(2) 2.10(3) 2.9358(18) 175(2) 1_545
O4 H4B O1 0.86(3) 2.14(3) 2.9796(18) 166(2) 2_665
O4 H4B O2 0.86(3) 2.53(2) 3.1467(17) 130.1(19) 2_665
O4 H4B N6 0.86(3) 2.67(3) 3.4595(18) 153(2) 2_665
N12 H12 N5 0.940(17) 1.845(18) 2.7840(16) 176.9(15) .
N12 H12 N6 0.940(17) 2.660(18) 3.5110(16) 150.9(13) .
N1 H1 N8 1.01(2) 1.77(2) 2.7425(17) 159.9(18) 2_665
N1 H1 N7 1.01(2) 2.70(2) 3.4613(16) 132.5(14) 2_665
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_4
C2 N8 N7 C5 -0.26(15) . .
N7 N8 C2 N10 -175.48(13) . .
N7 N8 C2 N9 0.13(15) . .
C5 N9 C2 N8 0.04(15) . .
N11 N9 C2 N8 -179.95(12) . .
C5 N9 C2 N10 175.90(13) . .
N11 N9 C2 N10 -4.1(2) . .
N8 N7 C5 N9 0.29(15) . .
N8 N7 C5 C5 -179.23(17) . 2_566
C2 N9 C5 N7 -0.21(15) . .
N11 N9 C5 N7 179.78(13) . .
C2 N9 C5 C5 179.32(16) . 2_566
N11 N9 C5 C5 -0.7(3) . 2_566
N15 C3 N12 N13 177.70(14) . .
N14 C3 N12 N13 -1.30(15) . .
N15 C3 N14 C4 -177.34(14) . .
N12 C3 N14 C4 1.69(15) . .
N15 C3 N14 N16 -0.5(2) . .
N12 C3 N14 N16 178.53(12) . .
N13 C4 N14 C3 -1.60(16) . .
C4 C4 N14 C3 177.42(17) 2_656 .
N13 C4 N14 N16 -177.97(14) . .
C4 C4 N14 N16 1.0(3) 2_656 .
N14 C4 N13 N12 0.79(15) . .
C4 C4 N13 N12 -178.22(17) 2_656 .
C3 N12 N13 C4 0.33(15) . .
C1 N1 N2 N3 0.18(15) . .
N1 N2 N3 N4 0.23(15) . .
N2 N3 N4 C1 -0.55(16) . .
C1 N5 N6 O2 -0.5(2) . .
C1 N5 N6 O1 179.63(13) . .
N3 N4 C1 N1 0.65(15) . .
N3 N4 C1 N5 -179.24(12) . .
N2 N1 C1 N4 -0.52(16) . .
N2 N1 C1 N5 179.35(15) . .
N6 N5 C1 N4 -177.82(13) . .
N6 N5 C1 N1 2.3(2) . .
