#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/90/4119050.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_4119050
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, H5 N2 '
_chemical_formula_sum            'C2 H7 N9 O4'
_chemical_formula_weight         221.17
_chemical_name_common
'hydrazinium 1,3-di(nitroimide)-1,2,3-triazolate'
_chemical_name_systematic
'hydrazinium 1,3-di(nitroimide)-1,2,3-triazolate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Joerg Stierstorfer'
_audit_creation_date
;
'Sat Jul 28 11:21:44 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                 91.855(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.6154(4)
_cell_length_b                   23.160(2)
_cell_length_c                   10.0335(9)
_cell_measurement_reflns_used    906
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.7057
_cell_measurement_theta_min      4.1500
_cell_volume                     839.69(14)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1416771000
_diffrn_orient_matrix_UB_12      -0.0184532000
_diffrn_orient_matrix_UB_13      -0.0224058000
_diffrn_orient_matrix_UB_21      -0.0623394000
_diffrn_orient_matrix_UB_22      0.0045988000
_diffrn_orient_matrix_UB_23      -0.0668857000
_diffrn_orient_matrix_UB_31      0.1207571000
_diffrn_orient_matrix_UB_32      0.0240263000
_diffrn_orient_matrix_UB_33      -0.0045080000
_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  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4255
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         4.16
_diffrn_source_current           40
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9765
_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    1.749
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0714
_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)+(0.0673P)²+1.5371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1822
_reflns_number_gt                1143
_reflns_number_total             1646
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310384y_si_001_3.cif
_cod_data_source_block           hx363
_cod_original_sg_symbol_Hall     -P2yn
_cod_database_code               4119050
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.7091(7) 0.12729(11) 0.3456(3) 0.0256(7) Uani 1 1 d
O2 O 0.5790(7) 0.06923(11) 0.5103(3) 0.0278(7) Uani 1 1 d
O3 O 0.7516(8) 0.38368(12) 0.3422(3) 0.0318(7) Uani 1 1 d
O4 O 0.6693(7) 0.44263(10) 0.5098(2) 0.0240(7) Uani 1 1 d
N1 N 0.4197(8) 0.21212(13) 0.4621(3) 0.0224(7) Uani 1 1 d
N2 N 0.5091(9) 0.25659(13) 0.5393(3) 0.0286(8) Uani 1 1 d
N3 N 0.4423(9) 0.30159(14) 0.4597(3) 0.0277(8) Uani 1 1 d
N4 N 0.4140(9) 0.15940(14) 0.5308(3) 0.0248(8) Uani 1 1 d
N5 N 0.5758(8) 0.11864(13) 0.4577(3) 0.0228(7) Uani 1 1 d
N6 N 0.4595(9) 0.35566(14) 0.5307(3) 0.0307(8) Uani 1 1 d
N7 N 0.6297(8) 0.39320(13) 0.4588(3) 0.0247(8) Uani 1 1 d
C1 C 0.2946(10) 0.22714(16) 0.3373(4) 0.0216(8) Uani 1 1 d
C2 C 0.3120(11) 0.28613(17) 0.3347(4) 0.0268(9) Uani 1 1 d
N8 N 0.9419(9) -0.00487(18) 0.3025(4) 0.0265(8) Uani 1 1 d
N9 N 0.6588(9) 0.01643(16) 0.2116(3) 0.0201(7) Uani 1 1 d
H8B H 0.909(10) -0.0393(18) 0.297(4) 0.012(11) Uiso 1 1 d
H9A H 0.705(11) -0.0036(19) 0.137(5) 0.031(12) Uiso 1 1 d
H1 H 0.209(11) 0.2025(19) 0.276(4) 0.034(12) Uiso 1 1 d
H9B H 0.439(14) 0.0053(19) 0.243(5) 0.040(13) Uiso 1 1 d
H9C H 0.674(10) 0.0516(19) 0.211(4) 0.019(11) Uiso 1 1 d
H2 H 0.283(11) 0.3063(18) 0.273(4) 0.024(12) Uiso 1 1 d
H8A H 0.887(12) 0.013(2) 0.376(5) 0.039(14) 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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 C1 114.0(3)
N2 N1 N4 113.4(3)
C1 N1 N4 131.6(3)
N1 N2 N3 102.8(3)
N2 N3 C2 113.2(3)
N2 N3 N6 112.3(3)
C2 N3 N6 133.3(3)
N5 N4 N1 109.3(3)
O1 N5 O2 121.5(3)
O1 N5 N4 124.4(3)
O2 N5 N4 114.1(3)
N7 N6 N3 108.7(3)
O4 N7 O3 119.2(3)
O4 N7 N6 115.6(3)
O3 N7 N6 125.1(3)
N1 C1 C2 105.0(3)
N1 C1 H1 125(3)
C2 C1 H1 130(3)
C1 C2 N3 104.9(4)
C1 C2 H2 127(3)
N3 C2 H2 127(3)
N9 N8 H8B 101(3)
N9 N8 H8A 102(3)
H8B N8 H8A 119(4)
N8 N9 H9A 102(3)
N8 N9 H9B 107(3)
H9A N9 H9B 109(4)
N8 N9 H9C 108(3)
H9A N9 H9C 119(4)
H9B N9 H9C 110(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N5 1.254(4)
O2 N5 1.260(4)
O3 N7 1.282(4)
O4 N7 1.260(4)
N1 N2 1.323(4)
N1 C1 1.363(5)
N1 N4 1.403(4)
N2 N3 1.330(4)
N3 C2 1.373(5)
N3 N6 1.441(5)
N4 N5 1.341(4)
N6 N7 1.298(4)
C1 C2 1.368(6)
C1 H1 0.89(4)
C2 H2 0.78(4)
N8 N9 1.436(4)
N8 H8B 0.81(4)
N8 H8A 0.87(5)
N9 H9A 0.90(5)
N9 H9B 0.90(5)
N9 H9C 0.82(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 O3 0.81(4) 2.33(4) 3.032(5) 146(4) 2_645
N9 H9A O4 0.90(5) 1.99(5) 2.886(5) 171(4) 2_645
N9 H9A O3 0.90(5) 2.62(4) 3.140(5) 117(3) 2_645
N9 H9A N7 0.90(5) 2.65(5) 3.426(5) 144(4) 2_645
N9 H9B N8 0.90(5) 1.93(5) 2.819(5) 170(4) 1_455
N9 H9C O1 0.82(4) 2.22(4) 2.901(5) 142(4) .
N8 H8A O2 0.87(5) 2.21(5) 3.032(5) 158(4) .
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 -0.8(4)
N4 N1 N2 N3 -170.9(3)
N1 N2 N3 C2 0.2(4)
N1 N2 N3 N6 169.8(3)
N2 N1 N4 N5 -137.1(3)
C1 N1 N4 N5 55.0(5)
N1 N4 N5 O1 -0.1(4)
N1 N4 N5 O2 -178.9(3)
N2 N3 N6 N7 138.5(3)
C2 N3 N6 N7 -54.6(5)
N3 N6 N7 O4 -179.1(3)
N3 N6 N7 O3 1.9(5)
N2 N1 C1 C2 1.0(4)
N4 N1 C1 C2 168.9(4)
N1 C1 C2 N3 -0.8(4)
N2 N3 C2 C1 0.4(5)
N6 N3 C2 C1 -166.3(4)
