#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/90/4119049.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_4119049
loop_
_publ_author_name
'Thomas M. Klapötke'
'Christian Petermayer'
'Davin G. Piercey'
'Jörg Stierstorfer'
_publ_contact_author_address
;
Department Chemie
Ludwig-Maximilians Universität
Butenandtstraße 5-13 (Haus D)
D-81377 München
Bundesrepublik Deutschland
;
_publ_contact_author_email       tmk@cup.uni-muenchen.de
_publ_contact_author_fax         '+49 89 2180 77492'
_publ_contact_author_name        'Thomas M. Klapoẗke'
_publ_contact_author_phone       '+49 89 2180 77491'
_publ_section_title
;
 1,3-Bis(nitroimido)-1,2,3-triazolate Anion, the N-Nitroimide Moiety, and
 the Strategy of Alternating Positive and Negative Charges in the Design
 of Energetic Materials
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20827
_journal_page_last               20836
_journal_paper_doi               10.1021/ja310384y
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C2 H2 N7 O4, H4 N '
_chemical_formula_sum            'C2 H6 N8 O4'
_chemical_formula_weight         206.15
_chemical_name_common            'ammonium 1,3-di(nitroimide)-1,2,3-triazolate'
_chemical_name_systematic        'ammonium 1,3-di(nitroimide)-1,2,3-triazolate'
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Joerg Stierstorfer'
_audit_creation_date
;
'Fri Jul 20 08:52:33 2012'
;
_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             27.09.2012
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4299(2)
_cell_length_b                   5.6658(2)
_cell_length_c                   20.5491(8)
_cell_measurement_reflns_used    2537
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.2848
_cell_measurement_theta_min      4.3386
_cell_volume                     748.61(5)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1091859000
_diffrn_orient_matrix_UB_12      -0.0091052000
_diffrn_orient_matrix_UB_13      -0.0041416000
_diffrn_orient_matrix_UB_21      -0.0154645000
_diffrn_orient_matrix_UB_22      -0.0582303000
_diffrn_orient_matrix_UB_23      -0.0301747000
_diffrn_orient_matrix_UB_31      0.0008947000
_diffrn_orient_matrix_UB_32      0.1104803000
_diffrn_orient_matrix_UB_33      -0.0162474000
_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  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7842
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         4.67
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.99999
_exptl_absorpt_correction_T_min  0.91998
_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    1.829
_exptl_crystal_description       rod
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         927
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0380
_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)+(0.0664P)²+0.0461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                891
_reflns_number_total             927
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310384y_si_001_2.cif
_cod_data_source_block           hx348
_cod_original_sg_symbol_Hall     'P 2c -2n '
_cod_database_code               4119049
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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
_atom_site_refinement_flags
O1 O -0.0352(4) 0.2762(4) 0.36012(10) 0.0290(5) Uani 1 1 d .
O2 O 0.0320(4) 0.6543(4) 0.37138(10) 0.0285(5) Uani 1 1 d .
O3 O 0.3429(4) -0.1830(4) 0.08658(11) 0.0314(5) Uani 1 1 d .
O4 O 0.2550(4) -0.0183(4) -0.00555(11) 0.0292(5) Uani 1 1 d .
N1 N 0.1125(3) 0.2847(4) 0.24249(12) 0.0198(5) Uani 1 1 d .
N2 N 0.1352(3) 0.3383(4) 0.17982(12) 0.0209(5) Uani 1 1 d .
N3 N 0.1406(3) 0.1292(4) 0.15054(12) 0.0195(5) Uani 1 1 d .
N4 N 0.1200(4) 0.4909(4) 0.28016(12) 0.0223(5) Uani 1 1 d .
N5 N 0.0367(4) 0.4672(4) 0.33828(11) 0.0219(5) Uani 1 1 d .
N6 N 0.1365(4) 0.1435(4) 0.08254(11) 0.0219(5) Uani 1 1 d .
N7 N 0.2497(3) -0.0259(4) 0.05580(12) 0.0199(5) Uani 1 1 d .
C1 C 0.1049(4) 0.0467(5) 0.25359(15) 0.0218(5) Uani 1 1 d .
C2 C 0.1211(4) -0.0534(5) 0.19292(14) 0.0213(6) Uani 1 1 d .
N8 N 0.2895(5) -0.5150(4) -0.03315(13) 0.0255(5) Uani 1 1 d D
H2 H 0.139(5) -0.205(7) 0.177(2) 0.025(9) Uiso 1 1 d .
H1 H 0.097(6) -0.018(7) 0.292(2) 0.025(9) Uiso 1 1 d .
H8B H 0.238(12) -0.634(10) -0.054(3) 0.15(4) Uiso 1 1 d D
H8A H 0.271(8) -0.506(8) 0.0061(18) 0.050(15) Uiso 1 1 d D
H8C H 0.413(7) -0.509(10) -0.046(3) 0.08(2) Uiso 1 1 d D
H8D H 0.225(15) -0.396(11) -0.054(4) 0.15(3) Uiso 1 1 d 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
N2 N1 C1 113.0(2)
N2 N1 N4 109.9(2)
C1 N1 N4 136.9(2)
N3 N2 N1 103.7(2)
N2 N3 C2 112.7(2)
N2 N3 N6 113.6(2)
C2 N3 N6 133.0(2)
N5 N4 N1 113.7(2)
O1 N5 O2 121.4(2)
O1 N5 N4 124.1(2)
O2 N5 N4 114.5(2)
N7 N6 N3 111.2(2)
O3 N7 O4 121.2(2)
O3 N7 N6 124.9(3)
O4 N7 N6 113.9(2)
N1 C1 C2 104.6(3)
N1 C1 H1 125(3)
C2 C1 H1 131(3)
N3 C2 C1 105.9(2)
N3 C2 H2 117(2)
C1 C2 H2 136(3)
H8B N8 H8A 119(5)
H8B N8 H8C 104(5)
H8A N8 H8C 116(5)
H8B N8 H8D 100(6)
H8A N8 H8D 111(6)
H8C N8 H8D 105(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N5 1.259(3)
O2 N5 1.260(3)
O3 N7 1.246(3)
O4 N7 1.262(3)
N1 N2 1.331(3)
N1 C1 1.368(3)
N1 N4 1.402(3)
N2 N3 1.329(3)
N3 C2 1.358(3)
N3 N6 1.400(3)
N4 N5 1.316(3)
N6 N7 1.324(3)
C1 C2 1.374(4)
C1 H1 0.87(4)
C2 H2 0.93(4)
N8 H8B 0.87(4)
N8 H8A 0.82(4)
N8 H8C 0.84(4)
N8 H8D 0.89(4)
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
N8 H8B O4 0.87(4) 2.39(7) 2.916(3) 119(6) 1_545
N8 H8B O2 0.87(4) 2.45(8) 2.946(3) 117(6) 3_534
N8 H8B O2 0.87(4) 2.32(7) 2.957(3) 130(7) 2_554
N8 H8A O3 0.82(4) 2.51(4) 3.116(3) 132(4) .
N8 H8A N6 0.82(4) 2.68(4) 3.219(4) 126(4) 1_545
N8 H8C O4 0.84(4) 2.35(5) 3.052(4) 142(6) 4_545
N8 H8C O1 0.84(4) 2.64(5) 3.167(4) 122(5) 3_544
N8 H8D O1 0.89(4) 2.26(6) 3.052(4) 148(7) 2_554
N8 H8D O4 0.89(4) 2.37(7) 2.879(3) 116(6) .
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
C1 N1 N2 N3 0.4(3)
N4 N1 N2 N3 175.6(2)
N1 N2 N3 C2 0.3(3)
N1 N2 N3 N6 172.0(2)
N2 N1 N4 N5 160.0(2)
C1 N1 N4 N5 -26.5(4)
N1 N4 N5 O1 3.2(4)
N1 N4 N5 O2 -176.3(2)
N2 N3 N6 N7 145.5(2)
C2 N3 N6 N7 -45.0(4)
N3 N6 N7 O3 2.2(4)
N3 N6 N7 O4 -178.6(2)
N2 N1 C1 C2 -0.9(3)
N4 N1 C1 C2 -174.2(3)
N2 N3 C2 C1 -0.9(3)
N6 N3 C2 C1 -170.5(3)
N1 C1 C2 N3 1.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139121705
