#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:24:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178781 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/35/4103599.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_4103599
loop_
_publ_author_name
'Michael Göbel'
'Konstantin Karaghiosoff'
'Thomas M. Klapötke'
'Davin G. Piercey'
'Jörg Stierstorfer'
_publ_contact_author_address
;
Ludwig-Maximilian University,
Department of Chemistry,
Butenandtstrasse 5-13 (Haus D), 
D-81377 Munich
;
_publ_contact_author_name        'Thomas M. Klapötke'
_publ_section_title
;
 Nitrotetrazolate-2N-oxides and the Strategy of N-Oxide Introduction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17216
_journal_page_last               17226
_journal_paper_doi               10.1021/ja106892a
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C2 H9 N11 O3'
_chemical_formula_weight         235.20
_chemical_name_common            TAGNTX
_chemical_name_systematic
;
 triaminoguanidinium 5-nitro-2H-tetrazol-2-olate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-07-06 # Formatted by publCIF
;
_cell_angle_alpha                90.000
_cell_angle_beta                 93.724(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   10.267(3)
_cell_length_b                   12.622(2)
_cell_length_c                   7.370(3)
_cell_measurement_reflns_used    9798
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      4.26
_cell_volume                     953.1(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur3 CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9798
_diffrn_reflns_theta_full        30.11
_diffrn_reflns_theta_max         30.11
_diffrn_reflns_theta_min         4.26
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0332
_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)+(0.0396P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                1815
_reflns_number_total             2792
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja106892a_si_004.cif
_cod_data_source_block           xprep
_cod_database_code               4103599
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.35466(10) 0.61604(8) 0.62834(14) 0.0208(2) Uani 1 1 d
C2 C 0.15836(10) 0.25770(8) 0.79469(14) 0.0219(2) Uani 1 1 d
O1 O 0.12096(7) 0.56612(6) 0.90102(10) 0.0284(2) Uani 1 1 d
O2 O 0.53198(7) 0.62774(7) 0.45791(11) 0.0361(2) Uani 1 1 d
O3 O 0.34047(8) 0.61781(7) 0.31907(11) 0.0392(2) Uani 1 1 d
N1 N 0.23028(8) 0.58755(7) 0.64036(11) 0.0224(2) Uani 1 1 d
N2 N 0.22391(8) 0.59269(7) 0.81967(12) 0.0222(2) Uani 1 1 d
N3 N 0.33445(10) 0.62312(8) 0.90916(13) 0.0328(2) Uani 1 1 d
N4 N 0.42064(9) 0.63761(8) 0.78275(13) 0.0294(2) Uani 1 1 d
N5 N 0.41230(9) 0.62136(7) 0.45639(12) 0.0254(2) Uani 1 1 d
N6 N 0.07949(9) 0.34121(8) 0.77718(13) 0.0271(2) Uani 1 1 d
N7 N 0.11182(10) 0.16169(8) 0.75544(14) 0.0288(2) Uani 1 1 d
N8 N 0.28338(9) 0.26838(8) 0.84786(13) 0.0271(2) Uani 1 1 d
N9 N 0.33295(10) 0.36939(8) 0.89712(15) 0.0271(2) Uani 1 1 d
N10 N -0.05450(9) 0.32052(8) 0.73783(16) 0.0300(2) Uani 1 1 d
N11 N 0.20035(10) 0.07593(8) 0.77189(16) 0.0302(2) Uani 1 1 d
H6 H 0.1054(12) 0.4015(10) 0.8146(16) 0.029(3) Uiso 1 1 d
H7 H 0.0296(14) 0.1522(10) 0.7167(17) 0.036(4) Uiso 1 1 d
H8 H 0.3295(13) 0.2126(12) 0.8550(18) 0.041(4) Uiso 1 1 d
H9A H 0.3987(12) 0.3844(10) 0.8271(17) 0.032(4) Uiso 1 1 d
H9B H 0.3716(12) 0.3641(10) 1.0126(18) 0.031(3) Uiso 1 1 d
H10A H -0.0827(13) 0.3539(11) 0.6346(18) 0.036(4) Uiso 1 1 d
H10B H -0.0999(13) 0.3452(11) 0.8271(18) 0.040(4) Uiso 1 1 d
H11A H 0.1949(12) 0.0386(11) 0.6690(19) 0.037(4) Uiso 1 1 d
H11B H 0.1771(12) 0.0362(11) 0.8667(18) 0.039(4) 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
N4 C1 N1 116.08(10)
N4 C1 N5 122.42(10)
N1 C1 N5 121.49(9)
N8 C2 N7 119.05(10)
N8 C2 N6 121.35(10)
N7 C2 N6 119.60(10)
N2 N1 C1 99.31(8)
O1 N2 N1 122.89(9)
O1 N2 N3 122.77(10)
N1 N2 N3 114.28(9)
N2 N3 N4 105.99(9)
C1 N4 N3 104.33(10)
O3 N5 O2 124.21(10)
O3 N5 C1 118.15(10)
O2 N5 C1 117.64(9)
C2 N6 N10 116.89(10)
C2 N6 H6 120.3(9)
N10 N6 H6 121.0(8)
C2 N7 N11 117.38(10)
C2 N7 H7 121.2(9)
N11 N7 H7 121.4(9)
C2 N8 N9 119.63(10)
C2 N8 H8 117.4(10)
N9 N8 H8 122.9(10)
N8 N9 H9A 108.4(8)
N8 N9 H9B 107.4(8)
H9A N9 H9B 104.7(11)
N6 N10 H10A 110.0(8)
N6 N10 H10B 109.6(9)
H10A N10 H10B 107.9(13)
N7 N11 H11A 109.1(8)
N7 N11 H11B 106.8(8)
H11A N11 H11B 111.0(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N4 1.3145(15)
C1 N1 1.3352(14)
C1 N5 1.4346(16)
C2 N8 1.3244(15)
C2 N7 1.3276(15)
C2 N6 1.3303(14)
O1 N2 1.2929(12)
O2 N5 1.2307(13)
O3 N5 1.2138(13)
N1 N2 1.3289(15)
N2 N3 1.3316(14)
N3 N4 1.3384(14)
N6 N10 1.4117(15)
N6 H6 0.847(13)
N7 N11 1.4136(14)
N7 H7 0.882(14)
N8 N9 1.4116(14)
N8 H8 0.849(14)
N9 H9A 0.896(13)
N9 H9B 0.918(13)
N10 H10A 0.901(14)
N10 H10B 0.887(14)
N11 H11A 0.891(14)
N11 H11B 0.904(14)
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
N4 C1 N1 N2 -0.30(12)
N5 C1 N1 N2 179.01(9)
C1 N1 N2 O1 -176.41(9)
C1 N1 N2 N3 0.80(11)
O1 N2 N3 N4 176.19(9)
N1 N2 N3 N4 -1.02(12)
N1 C1 N4 N3 -0.27(13)
N5 C1 N4 N3 -179.58(9)
N2 N3 N4 C1 0.73(12)
N4 C1 N5 O3 -167.86(11)
N1 C1 N5 O3 12.87(15)
N4 C1 N5 O2 13.14(15)
N1 C1 N5 O2 -166.13(10)
N8 C2 N6 N10 -173.72(10)
N7 C2 N6 N10 7.39(15)
N8 C2 N7 N11 -0.48(16)
N6 C2 N7 N11 178.44(10)
N7 C2 N8 N9 -177.43(10)
N6 C2 N8 N9 3.67(16)
