#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:51:45 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233355 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/58/7235816.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_7235816
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         'C2 N12 O4, C4 H10 N10'
_chemical_formula_sum            'C6 H10 N22 O4'
_chemical_formula_weight         454.36
_chemical_name_common
'5,5-bis(2,3-diamino-1,2,4-triazolium) 1,1-dinitramino-5,5-bistetrazolate'
_chemical_name_systematic
'5,5-bis(2,3-diamino-1,2,4-triazolium) 1,1-dinitramino-5,5-bistetrazolate'
_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 21:39:41 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                81.266(7)
_cell_angle_beta                 75.251(7)
_cell_angle_gamma                85.638(7)
_cell_formula_units_Z            1
_cell_length_a                   6.3892(6)
_cell_length_b                   8.2420(7)
_cell_length_c                   8.4392(7)
_cell_measurement_reflns_used    1490
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.8310
_cell_measurement_theta_min      4.6190
_cell_volume                     424.45(7)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0177616000
_diffrn_orient_matrix_UB_12      0.0251735000
_diffrn_orient_matrix_UB_13      -0.0864023000
_diffrn_orient_matrix_UB_21      0.0957129000
_diffrn_orient_matrix_UB_22      -0.0508962000
_diffrn_orient_matrix_UB_23      -0.0139410000
_diffrn_orient_matrix_UB_31      -0.0610123000
_diffrn_orient_matrix_UB_32      -0.0660948000
_diffrn_orient_matrix_UB_33      -0.0062782000
_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  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6245
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         4.13
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9425
_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    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.051
_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     165
_refine_ls_number_reflns         1750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0356
_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)+(0.0369P)²+0.1063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                1390
_reflns_number_total             1750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ta05964f2.cif
_cod_data_source_block           jx227
_cod_original_cell_volume        424.45(6)
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               7235816
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
O1 O 0.1278(2) 0.04267(15) 0.62882(15) 0.0337(3) Uani 1 1 d
O2 O 0.2924(2) 0.27452(15) 0.53984(15) 0.0312(3) Uani 1 1 d
N1 N 0.2860(2) -0.00472(16) 0.87740(16) 0.0191(3) Uani 1 1 d
N2 N 0.4412(2) -0.12044(17) 0.89562(17) 0.0234(3) Uani 1 1 d
N3 N 0.3503(2) -0.22967(17) 1.01708(17) 0.0235(3) Uani 1 1 d
N4 N 0.1384(2) -0.18771(16) 1.07904(17) 0.0227(3) Uani 1 1 d
N5 N 0.3416(2) 0.13920(16) 0.76853(16) 0.0224(3) Uani 1 1 d
N6 N 0.2490(2) 0.14593(17) 0.64404(16) 0.0226(3) Uani 1 1 d
C1 C 0.1016(3) -0.04665(18) 0.99110(19) 0.0185(3) Uani 1 1 d
N7 N 1.0930(2) 0.32786(17) 0.28931(17) 0.0224(3) Uani 1 1 d
N8 N 1.1709(2) 0.39394(16) 0.12685(16) 0.0206(3) Uani 1 1 d
N9 N 0.8155(2) 0.43750(15) 0.21042(15) 0.0166(3) Uani 1 1 d
N10 N 0.5981(2) 0.49004(19) 0.22169(17) 0.0204(3) Uani 1 1 d
N11 N 0.7569(3) 0.31154(19) 0.49043(18) 0.0261(3) Uani 1 1 d
C2 C 0.8813(3) 0.35426(19) 0.34151(19) 0.0183(3) Uani 1 1 d
C3 C 1.0002(3) 0.45836(18) 0.08190(18) 0.0165(3) Uani 1 1 d
H10A H 0.555(3) 0.447(2) 0.140(3) 0.035(6) Uiso 1 1 d
H7A H 1.179(3) 0.290(2) 0.352(3) 0.037(6) Uiso 1 1 d
H11B H 0.620(4) 0.323(3) 0.502(3) 0.040(6) Uiso 1 1 d
H10B H 0.598(3) 0.601(3) 0.197(3) 0.041(6) Uiso 1 1 d
H11A H 0.816(4) 0.239(3) 0.562(3) 0.046(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
N2 N1 C1 108.78(12) .
N2 N1 N5 119.17(13) .
C1 N1 N5 131.43(14) .
N3 N2 N1 105.96(13) .
N2 N3 N4 111.19(12) .
C1 N4 N3 105.66(13) .
N6 N5 N1 109.47(12) .
O1 N6 O2 121.85(13) .
O1 N6 N5 125.22(13) .
O2 N6 N5 112.90(13) .
N4 C1 N1 108.40(14) .
N4 C1 C1 126.59(18) 2_557
N1 C1 C1 125.00(17) 2_557
C2 N7 N8 112.19(13) .
C2 N7 H7A 125.2(14) .
N8 N7 H7A 121.7(14) .
C3 N8 N7 104.03(13) .
C2 N9 C3 106.09(13) .
C2 N9 N10 121.92(13) .
C3 N9 N10 131.95(13) .
N9 N10 H10A 106.9(13) .
N9 N10 H10B 106.1(13) .
H10A N10 H10B 108.4(18) .
C2 N11 H11B 117.3(14) .
C2 N11 H11A 117.2(14) .
H11B N11 H11A 121.6(19) .
N11 C2 N7 127.90(15) .
N11 C2 N9 126.03(16) .
N7 C2 N9 106.06(13) .
N8 C3 N9 111.61(13) .
N8 C3 C3 124.69(18) 2_765
N9 C3 C3 123.70(18) 2_765
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N6 1.2350(17) .
O2 N6 1.2693(17) .
N1 N2 1.3439(19) .
N1 C1 1.347(2) .
N1 N5 1.3945(18) .
N2 N3 1.3018(19) .
N3 N4 1.360(2) .
N4 C1 1.3203(19) .
N5 N6 1.3231(18) .
C1 C1 1.443(3) 2_557
N7 C2 1.323(2) .
N7 N8 1.3752(18) .
N7 H7A 0.86(2) .
N8 C3 1.295(2) .
N9 C2 1.354(2) .
N9 C3 1.3857(19) .
N9 N10 1.4070(18) .
N10 H10A 0.93(2) .
N10 H10B 0.91(2) .
N11 C2 1.317(2) .
N11 H11B 0.86(2) .
N11 H11A 0.91(2) .
C3 C3 1.447(3) 2_765
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 H10A N3 0.93(2) 2.34(2) 3.105(2) 139.3(16) 2_656
N10 H10A N8 0.93(2) 2.56(2) 3.218(2) 128.3(16) 1_455
N7 H7A O2 0.86(2) 1.89(2) 2.7005(18) 156(2) 1_655
N11 H11B O2 0.86(2) 2.09(2) 2.923(2) 163(2) .
N10 H10B N5 0.91(2) 2.28(2) 3.125(2) 155.1(18) 2_666
N10 H10B N3 0.91(2) 2.64(2) 3.2327(19) 123.2(16) 1_564
N11 H11A O1 0.91(2) 2.59(2) 3.422(2) 151.4(18) 1_655
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_4
C1 N1 N2 N3 0.44(17) .
N5 N1 N2 N3 172.47(13) .
N1 N2 N3 N4 -0.08(17) .
N2 N3 N4 C1 -0.32(18) .
N2 N1 N5 N6 114.20(15) .
C1 N1 N5 N6 -75.9(2) .
N1 N5 N6 O1 1.6(2) .
N1 N5 N6 O2 179.84(13) .
N3 N4 C1 N1 0.58(17) .
N3 N4 C1 C1 179.1(2) 2_557
N2 N1 C1 N4 -0.66(18) .
N5 N1 C1 N4 -171.36(15) .
N2 N1 C1 C1 -179.25(19) 2_557
N5 N1 C1 C1 10.0(3) 2_557
C2 N7 N8 C3 -1.02(18) .
N8 N7 C2 N11 -178.17(16) .
N8 N7 C2 N9 0.98(18) .
C3 N9 C2 N11 178.63(16) .
N10 N9 C2 N11 0.6(3) .
C3 N9 C2 N7 -0.53(17) .
N10 N9 C2 N7 -178.58(14) .
N7 N8 C3 N9 0.65(17) .
N7 N8 C3 C3 -179.16(19) 2_765
C2 N9 C3 N8 -0.09(18) .
N10 N9 C3 N8 177.68(15) .
C2 N9 C3 C3 179.71(18) 2_765
N10 N9 C3 C3 -2.5(3) 2_765
