#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/11/4001177.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_4001177
loop_
_publ_author_name
'Klapötke, Thomas M.'
'Stierstorfer, Jörg'
'Wallek, Andreas U.'
_publ_section_title
;
 Nitrogen-Rich Salts of 1-Methyl-5-nitriminotetrazolate: An Auspicious
 Class of Thermally Stable Energetic Materials
;
_journal_issue                   13
_journal_name_full               'Chemistry of Materials'
_journal_page_first              4519
_journal_paper_doi               10.1021/cm8004166
_journal_volume                  20
_journal_year                    2008
_chemical_formula_moiety         'C H9 N6, C2 H3 N6 O2'
_chemical_formula_sum            'C3 H12 N12 O2'
_chemical_formula_weight         248.25
_chemical_name_common
'Triaminoguanidinium 1-methyl-5-nitriminotetrazolate'
_chemical_name_systematic
'Triaminoguanidinium 1-methyl-5-nitriminotetrazolate'
_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             04-Sep-07
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.311(2)
_cell_angle_beta                 103.776(2)
_cell_angle_gamma                103.123(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8650(2)
_cell_length_b                   7.9800(2)
_cell_length_c                   10.5180(3)
_cell_measurement_reflns_used    7503
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     525.60(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_UB_11      0.0130854
_diffrn_orient_matrix_UB_12      -0.0530780
_diffrn_orient_matrix_UB_13      0.0791261
_diffrn_orient_matrix_UB_21      0.0968422
_diffrn_orient_matrix_UB_22      0.1165330
_diffrn_orient_matrix_UB_23      0.0609180
_diffrn_orient_matrix_UB_31      -0.1223387
_diffrn_orient_matrix_UB_32      0.0374857
_diffrn_orient_matrix_UB_33      0.0182316
_diffrn_radiation_collimation    0.5
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3943
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.19
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                1886
_reflns_number_total             2056
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm8004166-file008.cif
_cod_data_source_block           ln466
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4001177
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 0.08890(16) -0.24817(13) 0.59036(10) 0.0265(3) Uani 1 1 d
O2 O 0.23558(19) -0.02810(15) 0.51862(11) 0.0320(3) Uani 1 1 d
N9 N 0.55951(19) -0.64496(16) 0.72258(13) 0.0222(3) Uani 1 1 d
N1 N 0.26869(19) 0.07841(16) 0.95997(12) 0.0236(3) Uani 1 1 d
N6 N 0.19483(18) -0.08891(15) 0.61306(12) 0.0212(3) Uani 1 1 d
N8 N 0.18532(19) -0.58543(18) 0.69757(14) 0.0245(3) Uani 1 1 d
N4 N 0.1704(2) -0.20514(17) 0.85996(13) 0.0264(3) Uani 1 1 d
N7 N 0.34298(18) -0.47489(17) 0.66224(13) 0.0243(3) Uani 1 1 d
N5 N 0.26813(19) 0.02292(15) 0.73521(12) 0.0234(3) Uani 1 1 d
N2 N 0.2355(2) -0.00799(18) 1.05388(13) 0.0285(3) Uani 1 1 d
C3 C 0.5297(2) -0.50226(17) 0.68281(13) 0.0186(3) Uani 1 1 d
N11 N 0.6850(2) -0.38463(16) 0.66420(13) 0.0237(3) Uani 1 1 d
N10 N 0.7559(2) -0.67750(18) 0.73320(15) 0.0276(3) Uani 1 1 d
N3 N 0.1772(2) -0.17678(18) 0.99321(13) 0.0301(3) Uani 1 1 d
C1 C 0.2296(2) -0.04300(18) 0.84089(14) 0.0205(3) Uani 1 1 d
N12 N 0.6443(2) -0.22746(17) 0.63671(14) 0.0273(3) Uani 1 1 d
C2 C 0.3302(3) 0.2725(2) 0.99110(17) 0.0310(4) Uani 1 1 d
H9 H 0.452(3) -0.729(3) 0.7173(19) 0.034(5) Uiso 1 1 d
H7 H 0.328(3) -0.376(3) 0.6367(19) 0.033(5) Uiso 1 1 d
H12B H 0.696(3) -0.204(3) 0.569(2) 0.040(5) Uiso 1 1 d
H12A H 0.708(3) -0.136(3) 0.714(2) 0.040(5) Uiso 1 1 d
H2C H 0.295(4) 0.308(3) 0.906(3) 0.060(7) Uiso 1 1 d
H11 H 0.804(3) -0.396(3) 0.685(2) 0.036(5) Uiso 1 1 d
H2A H 0.246(4) 0.318(3) 1.043(2) 0.056(6) Uiso 1 1 d
H8B H 0.134(3) -0.509(3) 0.749(2) 0.040(5) Uiso 1 1 d
H2B H 0.469(4) 0.317(3) 1.034(3) 0.060(7) Uiso 1 1 d
H10B H 0.795(3) -0.711(3) 0.815(2) 0.041(5) Uiso 1 1 d
H8A H 0.088(3) -0.645(3) 0.621(2) 0.038(5) Uiso 1 1 d
H10A H 0.739(3) -0.770(3) 0.661(2) 0.043(5) 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 7 -7 0.051000
-1 -6 6 0.040000
3 -3 -4 0.070000
-6 5 6 0.067000
9 -1 4 0.072000
-6 1 -3 0.070000
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 N9 N10 118.15(12)
C3 N9 H9 118.7(13)
N10 N9 H9 120.5(13)
N2 N1 C1 108.85(12)
N2 N1 C2 121.80(12)
C1 N1 C2 129.32(13)
O2 N6 O1 120.77(11)
O2 N6 N5 116.29(12)
O1 N6 N5 122.94(11)
N7 N8 H8B 105.4(13)
N7 N8 H8A 106.0(13)
H8B N8 H8A 109.3(18)
C1 N4 N3 105.43(12)
C3 N7 N8 119.49(12)
C3 N7 H7 117.8(12)
N8 N7 H7 122.2(12)
N6 N5 C1 117.08(12)
N3 N2 N1 106.40(12)
N7 C3 N9 119.71(12)
N7 C3 N11 119.05(13)
N9 C3 N11 121.23(13)
C3 N11 N12 116.95(12)
C3 N11 H11 118.7(14)
N12 N11 H11 122.9(14)
N9 N10 H10B 107.0(12)
N9 N10 H10A 107.7(13)
H10B N10 H10A 109.6(18)
N2 N3 N4 111.39(12)
N4 C1 N1 107.93(12)
N4 C1 N5 135.48(13)
N1 C1 N5 116.47(12)
N11 N12 H12B 108.8(13)
N11 N12 H12A 108.3(12)
H12B N12 H12A 110.6(18)
N1 C2 H2C 108.8(15)
N1 C2 H2A 109.4(14)
H2C C2 H2A 105(2)
N1 C2 H2B 109.9(16)
H2C C2 H2B 111(2)
H2A C2 H2B 113(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N6 1.2568(15)
O2 N6 1.2491(16)
N9 C3 1.3288(18)
N9 N10 1.4130(17)
N9 H9 0.86(2)
N1 N2 1.3438(17)
N1 C1 1.3509(18)
N1 C2 1.4567(19)
N6 N5 1.3186(17)
N8 N7 1.4051(17)
N8 H8B 0.92(2)
N8 H8A 0.88(2)
N4 C1 1.3347(19)
N4 N3 1.3628(18)
N7 C3 1.3232(18)
N7 H7 0.90(2)
N5 C1 1.3742(18)
N2 N3 1.295(2)
C3 N11 1.3319(18)
N11 N12 1.4135(17)
N11 H11 0.83(2)
N10 H10B 0.94(2)
N10 H10A 0.91(2)
N12 H12B 0.90(2)
N12 H12A 0.92(2)
C2 H2C 0.98(3)
C2 H2A 0.97(2)
C2 H2B 0.90(3)
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
N9 H9 N5 0.86(2) 2.17(2) 2.9834(17) 159.9(18) 1_545
N7 H7 O1 0.90(2) 2.13(2) 2.8686(17) 138.4(16) .
N7 H7 N6 0.90(2) 2.68(2) 3.5476(17) 160.5(16) .
N12 H12B O2 0.90(2) 2.24(2) 2.9484(17) 136.0(17) 2_656
N12 H12A N2 0.92(2) 2.38(2) 3.2281(19) 153.8(17) 2_657
N11 H11 O1 0.83(2) 2.56(2) 3.0761(16) 121.8(17) 1_655
N11 H11 N4 0.83(2) 2.64(2) 3.2868(18) 136.0(17) 1_655
N8 H8B N4 0.92(2) 2.40(2) 3.2137(19) 146.7(17) .
N10 H10B N3 0.94(2) 2.35(2) 3.2817(19) 169.0(17) 2_647
N8 H8A O1 0.88(2) 2.15(2) 3.0085(17) 163.9(18) 2_546
N10 H10A O2 0.91(2) 2.30(2) 3.1988(18) 168.0(18) 2_646
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
O2 N6 N5 C1 -178.31(12)
O1 N6 N5 C1 1.9(2)
C1 N1 N2 N3 -0.25(16)
C2 N1 N2 N3 177.96(13)
N8 N7 C3 N9 7.3(2)
N8 N7 C3 N11 -172.14(12)
N10 N9 C3 N7 175.08(13)
N10 N9 C3 N11 -5.5(2)
N7 C3 N11 N12 6.31(19)
N9 C3 N11 N12 -173.11(12)
N1 N2 N3 N4 -0.06(17)
C1 N4 N3 N2 0.35(17)
N3 N4 C1 N1 -0.49(15)
N3 N4 C1 N5 175.28(15)
N2 N1 C1 N4 0.48(16)
C2 N1 C1 N4 -177.57(14)
N2 N1 C1 N5 -176.22(12)
C2 N1 C1 N5 5.7(2)
N6 N5 C1 N4 16.9(2)
N6 N5 C1 N1 -167.61(12)
