#------------------------------------------------------------------------------
#$Date: 2025-08-21 13:21:36 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301847 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/98/7019822.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_7019822
loop_
_publ_author_name
'Klapötke, Thomas M'
'Piercey, Davin G.'
'Stierstorfer, Jörg'
_publ_section_title
;
 Amination of energetic anions: high-performing energetic materials.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9451
_journal_page_last               9459
_journal_paper_doi               10.1039/c2dt30684k
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C2 H4 N10'
_chemical_formula_sum            'C2 H4 N10'
_chemical_formula_weight         168.15
_chemical_name_common            5,5-bis(1-aminotetrazole)
_chemical_name_systematic        5,5-bis(1-aminotetrazole)
_space_group_IT_number           2
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Sat Nov 05 19:09:56 2011'
;
_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             07.11.2011
_cell_angle_alpha                90.106(9)
_cell_angle_beta                 90.874(9)
_cell_angle_gamma                106.336(9)
_cell_formula_units_Z            4
_cell_length_a                   6.2087(6)
_cell_length_b                   9.9845(10)
_cell_length_c                   10.6782(14)
_cell_measurement_reflns_used    1094
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.5639
_cell_measurement_theta_min      4.2455
_cell_volume                     635.14(12)
_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
;
_computing_publication_material
'PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).'
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1081085000
_diffrn_orient_matrix_UB_12      -0.0482162000
_diffrn_orient_matrix_UB_13      -0.0059342000
_diffrn_orient_matrix_UB_21      0.0469850000
_diffrn_orient_matrix_UB_22      -0.0557781000
_diffrn_orient_matrix_UB_23      0.0123383000
_diffrn_orient_matrix_UB_31      -0.0167887000
_diffrn_orient_matrix_UB_32      0.0066680000
_diffrn_orient_matrix_UB_33      0.0650091000
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3443
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         4.25
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_correction_T_min  0.9646
_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    1.759
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0539
_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)+(0.0547P)²+0.1524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                2034
_reflns_number_total             2592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30684k.txt
_cod_data_source_block           gx626
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_database_code               7019822
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
N1 N 0.0050(3) 0.6276(2) 0.38334(18) 0.0198(4) Uani 1 1 d
N5 N -0.1940(4) 0.6673(3) 0.3708(2) 0.0258(5) Uani 1 1 d
N6 N 0.0890(3) 0.3982(2) 0.12708(19) 0.0223(5) Uani 1 1 d
N7 N -0.0593(4) 0.3349(2) 0.0387(2) 0.0263(5) Uani 1 1 d
N4 N 0.2866(3) 0.5409(2) 0.36912(19) 0.0242(5) Uani 1 1 d
N3 N 0.3167(3) 0.6313(2) 0.4687(2) 0.0257(5) Uani 1 1 d
N2 N 0.1473(3) 0.6832(2) 0.47812(19) 0.0226(5) Uani 1 1 d
N8 N -0.2469(4) 0.3600(2) 0.0648(2) 0.0303(5) Uani 1 1 d
N10 N 0.3073(4) 0.3859(3) 0.1242(2) 0.0302(6) Uani 1 1 d
N9 N -0.2250(3) 0.4396(2) 0.1716(2) 0.0284(5) Uani 1 1 d
C2 C -0.0144(4) 0.4616(2) 0.2081(2) 0.0193(5) Uani 1 1 d
C1 C 0.0927(4) 0.5410(2) 0.3181(2) 0.0185(5) Uani 1 1 d
N11 N 0.4951(3) 0.8627(2) 0.11776(18) 0.0225(5) Uani 1 1 d
N15 N 0.6726(4) 0.8026(3) 0.1077(2) 0.0279(5) Uani 1 1 d
N14 N 0.2558(4) 0.9837(2) 0.1017(2) 0.0279(5) Uani 1 1 d
N12 N 0.3453(4) 0.8191(2) 0.2088(2) 0.0278(5) Uani 1 1 d
N13 N 0.2021(4) 0.8912(2) 0.1988(2) 0.0296(5) Uani 1 1 d
C3 C 0.4394(4) 0.9636(2) 0.0527(2) 0.0215(5) Uani 1 1 d
N18 N 0.7165(4) 0.0709(2) 0.3160(2) 0.0294(5) Uani 1 1 d
N20 N 1.2883(4) 0.1953(3) 0.3561(2) 0.0275(5) Uani 1 1 d
N17 N 0.9114(4) 0.1481(2) 0.2841(2) 0.0280(5) Uani 1 1 d
N16 N 1.0609(3) 0.1230(2) 0.36587(19) 0.0236(5) Uani 1 1 d
N19 N 0.7332(4) -0.0072(2) 0.4183(2) 0.0295(5) Uani 1 1 d
C4 C 0.9491(4) 0.0271(3) 0.4481(2) 0.0246(6) Uani 1 1 d
H15B H 0.800(6) 0.867(4) 0.105(3) 0.045(10) Uiso 1 1 d
H5B H -0.305(6) 0.594(4) 0.367(3) 0.047(10) Uiso 1 1 d
H20B H 1.326(5) 0.242(3) 0.426(3) 0.033(8) Uiso 1 1 d
H10A H 0.410(6) 0.477(4) 0.132(3) 0.061(11) Uiso 1 1 d
H15A H 0.661(6) 0.756(4) 0.025(4) 0.063(11) Uiso 1 1 d
H20A H 1.371(6) 0.133(4) 0.355(3) 0.048(10) Uiso 1 1 d
H5A H -0.180(6) 0.716(4) 0.295(3) 0.050(10) Uiso 1 1 d
H10B H 0.324(6) 0.342(4) 0.192(3) 0.052(11) 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'
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
C1 N1 N2 108.4(2) .
C1 N1 N5 133.4(2) .
N2 N1 N5 118.23(19) .
N1 N5 H5B 109(2) .
N1 N5 H5A 105(2) .
H5B N5 H5A 110(3) .
N7 N6 C2 108.6(2) .
N7 N6 N10 119.3(2) .
C2 N6 N10 132.1(2) .
N8 N7 N6 106.73(19) .
C1 N4 N3 105.30(19) .
N2 N3 N4 110.82(19) .
N3 N2 N1 106.30(19) .
N7 N8 N9 110.7(2) .
N6 N10 H10A 109(2) .
N6 N10 H10B 106(2) .
H10A N10 H10B 106(3) .
C2 N9 N8 105.17(19) .
N9 C2 N6 108.8(2) .
N9 C2 C1 126.5(2) .
N6 C2 C1 124.7(2) .
N4 C1 N1 109.2(2) .
N4 C1 C2 126.6(2) .
N1 C1 C2 124.2(2) .
N12 N11 C3 108.7(2) .
N12 N11 N15 118.8(2) .
C3 N11 N15 132.5(2) .
N11 N15 H15B 111(2) .
N11 N15 H15A 109(2) .
H15B N15 H15A 104(3) .
C3 N14 N13 105.4(2) .
N13 N12 N11 106.7(2) .
N12 N13 N14 110.8(2) .
N14 C3 N11 108.5(2) .
N14 C3 C3 126.4(3) 2_675
N11 C3 C3 125.1(3) 2_675
N17 N18 N19 110.9(2) .
N16 N20 H20B 106.3(19) .
N16 N20 H20A 109(2) .
H20B N20 H20A 105(3) .
N18 N17 N16 107.0(2) .
N17 N16 C4 108.1(2) .
N17 N16 N20 119.8(2) .
C4 N16 N20 132.1(2) .
C4 N19 N18 105.5(2) .
N19 C4 N16 108.5(2) .
N19 C4 C4 126.4(3) 2_756
N16 C4 C4 125.1(3) 2_756
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.343(3) .
N1 N2 1.345(3) .
N1 N5 1.404(3) .
N5 H5B 0.85(3) .
N5 H5A 0.94(4) .
N6 N7 1.335(3) .
N6 C2 1.343(3) .
N6 N10 1.396(3) .
N7 N8 1.293(3) .
N4 C1 1.314(3) .
N4 N3 1.370(3) .
N3 N2 1.301(3) .
N8 N9 1.371(3) .
N10 H10A 0.95(4) .
N10 H10B 0.86(4) .
N9 C2 1.317(3) .
C2 C1 1.458(3) .
N11 N12 1.342(3) .
N11 C3 1.345(3) .
N11 N15 1.400(3) .
N15 H15B 0.87(3) .
N15 H15A 0.99(4) .
N14 C3 1.326(3) .
N14 N13 1.371(3) .
N12 N13 1.295(3) .
C3 C3 1.443(5) 2_675
N18 N17 1.290(3) .
N18 N19 1.363(3) .
N20 N16 1.399(3) .
N20 H20B 0.87(3) .
N20 H20A 0.91(4) .
N17 N16 1.340(3) .
N16 C4 1.349(3) .
N19 C4 1.320(3) .
C4 C4 1.447(5) 2_756
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
N15 H15B N13 0.87(3) 2.62(3) 3.286(3) 134(3) 1_655
N5 H5B N4 0.85(3) 2.44(3) 3.115(3) 137(3) 1_455
N20 H20B N3 0.87(3) 2.48(3) 3.157(3) 136(2) 2_766
N20 H20B N5 0.87(3) 2.59(3) 3.350(3) 147(2) 2_666
N10 H10A N9 0.95(4) 2.43(4) 2.838(3) 106(3) 1_655
N15 H15A N10 0.99(4) 2.18(4) 3.133(3) 162(3) 2_665
N15 H15A N8 0.99(4) 2.67(4) 3.231(3) 116(3) 2_565
N20 H20A N18 0.91(4) 2.44(4) 3.269(3) 152(3) 1_655
N5 H5A N15 0.94(4) 2.45(4) 3.313(3) 154(3) 1_455
N10 H10B N20 0.86(4) 2.26(4) 3.110(4) 167(3) 1_455
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
C2 N6 N7 N8 0.5(3) .
N10 N6 N7 N8 178.5(2) .
C1 N4 N3 N2 0.5(3) .
N4 N3 N2 N1 -0.6(3) .
C1 N1 N2 N3 0.4(3) .
N5 N1 N2 N3 -179.5(2) .
N6 N7 N8 N9 -0.4(3) .
N7 N8 N9 C2 0.2(3) .
N8 N9 C2 N6 0.1(3) .
N8 N9 C2 C1 -179.8(2) .
N7 N6 C2 N9 -0.3(3) .
N10 N6 C2 N9 -178.0(3) .
N7 N6 C2 C1 179.6(2) .
N10 N6 C2 C1 1.9(4) .
N3 N4 C1 N1 -0.2(3) .
N3 N4 C1 C2 179.6(2) .
N2 N1 C1 N4 -0.1(3) .
N5 N1 C1 N4 179.8(2) .
N2 N1 C1 C2 -179.9(2) .
N5 N1 C1 C2 0.0(4) .
N9 C2 C1 N4 165.5(3) .
N6 C2 C1 N4 -14.4(4) .
N9 C2 C1 N1 -14.8(4) .
N6 C2 C1 N1 165.4(2) .
C3 N11 N12 N13 0.3(3) .
N15 N11 N12 N13 179.3(2) .
N11 N12 N13 N14 -0.3(3) .
C3 N14 N13 N12 0.3(3) .
N13 N14 C3 N11 -0.1(3) .
N13 N14 C3 C3 179.8(3) 2_675
N12 N11 C3 N14 -0.1(3) .
N15 N11 C3 N14 -178.9(2) .
N12 N11 C3 C3 180.0(3) 2_675
N15 N11 C3 C3 1.2(5) 2_675
N19 N18 N17 N16 -0.4(3) .
N18 N17 N16 C4 0.2(3) .
N18 N17 N16 N20 -178.5(2) .
N17 N18 N19 C4 0.4(3) .
N18 N19 C4 N16 -0.3(3) .
N18 N19 C4 C4 179.2(3) 2_756
N17 N16 C4 N19 0.0(3) .
N20 N16 C4 N19 178.6(2) .
N17 N16 C4 C4 -179.4(3) 2_756
N20 N16 C4 C4 -0.9(5) 2_756
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139158670
