#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:44:35 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/57/7235794.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_7235794
loop_
_publ_author_name
'Bian, Chengming'
'Zhang, Man'
'Li, Chuan'
'Zhou, Zhiming'
_publ_section_title
;
 3-Nitro-1-(2H-tetrazol-5-yl)-1H-1,2,4-triazol-5-amine (HANTT) and its
 energetic salts: highly thermally stable energetic materials with low
 sensitivity
;
_journal_issue                   1
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              163
_journal_paper_doi               10.1039/C4TA04107K
_journal_volume                  3
_journal_year                    2015
_chemical_formula_sum            'C4 H9 N12 O2.5'
_chemical_formula_weight         265.23
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.760(9)
_cell_angle_beta                 84.240(8)
_cell_angle_gamma                68.063(9)
_cell_formula_units_Z            4
_cell_length_a                   7.0181(17)
_cell_length_b                   8.833(2)
_cell_length_c                   18.795(6)
_cell_measurement_reflns_used    4312
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      31.502
_cell_measurement_theta_min      2.182
_cell_volume                     1073.5(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      163(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16124
_diffrn_reflns_theta_full        31.51
_diffrn_reflns_theta_max         31.51
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_type   Multi-scans
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    X,Y,Z,Ueq
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0391P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                5120
_reflns_number_total             7031
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ta04107k2.cif
_cod_data_source_block           bo3184
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C4 H9 N12 O2.50'
_cod_database_code               7235794
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 0.56137(13) 0.80783(11) 0.31962(4) 0.0343(2) Uani 1 1 d
O2 O 0.60579(13) 0.70424(10) 0.42898(4) 0.03183(19) Uani 1 1 d
O3 O 0.76348(15) -0.11342(11) 0.18073(5) 0.0410(2) Uani 1 1 d
O4 O 0.75631(14) -0.16037(10) 0.06969(5) 0.0371(2) Uani 1 1 d
O5 O 0.90860(15) 0.52267(11) 0.25443(5) 0.02940(19) Uani 1 1 d
N1 N 0.26655(13) 1.08861(11) 0.36486(5) 0.02172(18) Uani 1 1 d
N2 N 0.29966(13) 0.96876(10) 0.47817(5) 0.02074(18) Uani 1 1 d
N3 N 0.15022(13) 1.12327(10) 0.47782(4) 0.02011(18) Uani 1 1 d
N4 N 0.00064(16) 1.34304(12) 0.39298(5) 0.0259(2) Uani 1 1 d
N5 N 0.52095(14) 0.81253(11) 0.38451(5) 0.02353(19) Uani 1 1 d
N6 N 0.06171(14) 1.10305(11) 0.60350(5) 0.0244(2) Uani 1 1 d
N7 N -0.08091(15) 1.20679(12) 0.64828(5) 0.0283(2) Uani 1 1 d
N8 N -0.18197(15) 1.34239(12) 0.61206(5) 0.0290(2) Uani 1 1 d
N9 N -0.11128(14) 1.33445(11) 0.54234(5) 0.0263(2) Uani 1 1 d
N10 N 0.75304(14) 0.19406(11) 0.14358(5) 0.0245(2) Uani 1 1 d
N11 N 0.75818(14) 0.13608(11) 0.02755(5) 0.02366(19) Uani 1 1 d
N12 N 0.75848(14) 0.29064(11) 0.03150(4) 0.02203(19) Uani 1 1 d
N13 N 0.74916(16) 0.46579(13) 0.12223(6) 0.0298(2) Uani 1 1 d
N14 N 0.75839(15) -0.07363(12) 0.11673(5) 0.0280(2) Uani 1 1 d
N15 N 0.78026(16) 0.34182(12) -0.09578(5) 0.0296(2) Uani 1 1 d
N16 N 0.76921(17) 0.47720(13) -0.13763(5) 0.0337(2) Uani 1 1 d
N17 N 0.74207(16) 0.59796(13) -0.09725(5) 0.0333(2) Uani 1 1 d
N18 N 0.73393(15) 0.54696(12) -0.02754(5) 0.0297(2) Uani 1 1 d
N19 N 0.53145(16) 0.30838(13) 0.40125(5) 0.0267(2) Uani 1 1 d
N20 N 0.70800(16) 0.16537(12) 0.30382(6) 0.0294(2) Uani 1 1 d
N21 N 0.44897(17) 0.41614(13) 0.28799(6) 0.0328(2) Uani 1 1 d
N22 N 0.25136(18) 0.13683(14) 0.20904(5) 0.0328(2) Uani 1 1 d
N23 N 0.26095(17) 0.05252(14) 0.09688(5) 0.0300(2) Uani 1 1 d
N24 N 0.23359(18) -0.11325(14) 0.19571(6) 0.0334(2) Uani 1 1 d
C1 C 0.13191(16) 1.19389(13) 0.40948(5) 0.0200(2) Uani 1 1 d
C2 C 0.35868(16) 0.96038(13) 0.40992(5) 0.0199(2) Uani 1 1 d
C3 C 0.03549(16) 1.18649(12) 0.54095(5) 0.0198(2) Uani 1 1 d
C4 C 0.75523(16) 0.32387(13) 0.10154(5) 0.0223(2) Uani 1 1 d
C5 C 0.75574(16) 0.08950(13) 0.09521(5) 0.0228(2) Uani 1 1 d
C6 C 0.75785(16) 0.39161(13) -0.03044(5) 0.0214(2) Uani 1 1 d
C7 C 0.56442(17) 0.29531(13) 0.33069(5) 0.0219(2) Uani 1 1 d
C8 C 0.24844(17) 0.02481(14) 0.16771(6) 0.0241(2) Uani 1 1 d
H4A H -0.009(2) 1.3851(16) 0.3470(7) 0.034(4) Uiso 1 1 d
H4B H -0.076(2) 1.4033(18) 0.4251(8) 0.041(4) Uiso 1 1 d
H13A H 0.755(2) 0.5486(17) 0.0890(7) 0.038(4) Uiso 1 1 d
H13B H 0.766(2) 0.4733(19) 0.1666(9) 0.052(5) Uiso 1 1 d
H19A H 0.435(2) 0.3992(19) 0.4168(8) 0.045(4) Uiso 1 1 d
H19B H 0.597(2) 0.2320(19) 0.4304(8) 0.046(4) Uiso 1 1 d
H20A H 0.783(2) 0.0811(19) 0.3333(8) 0.052(5) Uiso 1 1 d
H20B H 0.728(2) 0.1609(16) 0.2579(8) 0.037(4) Uiso 1 1 d
H21A H 0.350(2) 0.503(2) 0.3076(8) 0.051(4) Uiso 1 1 d
H21B H 0.466(2) 0.4158(18) 0.2408(8) 0.046(4) Uiso 1 1 d
H22A H 0.261(2) 0.1164(17) 0.2578(8) 0.042(4) Uiso 1 1 d
H22B H 0.259(2) 0.225(2) 0.1891(8) 0.052(5) Uiso 1 1 d
H23A H 0.258(2) -0.0213(18) 0.0701(8) 0.043(4) Uiso 1 1 d
H23B H 0.266(2) 0.149(2) 0.0787(8) 0.061(5) Uiso 1 1 d
H24A H 0.231(2) -0.1833(18) 0.1664(8) 0.044(4) Uiso 1 1 d
H24B H 0.211(2) -0.1260(19) 0.2409(9) 0.049(4) Uiso 1 1 d
H05A H 0.820(3) 0.615(2) 0.2672(9) 0.058(5) Uiso 1 1 d
H05B H 0.994(3) 0.540(2) 0.2284(9) 0.062(6) 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
H05A O5 H05B 108.2(17)
C1 N1 C2 101.89(9)
C2 N2 N3 99.99(8)
C1 N3 N2 110.44(8)
C1 N3 C3 128.50(9)
N2 N3 C3 121.01(8)
C1 N4 H4A 121.3(9)
C1 N4 H4B 121.1(10)
H4A N4 H4B 117.6(13)
O2 N5 O1 125.35(9)
O2 N5 C2 118.10(9)
O1 N5 C2 116.55(9)
C3 N6 N7 103.18(9)
N8 N7 N6 109.33(9)
N7 N8 N9 110.40(9)
C3 N9 N8 102.46(9)
C4 N10 C5 101.82(9)
C5 N11 N12 100.32(9)
C4 N12 N11 110.28(8)
C4 N12 C6 128.73(9)
N11 N12 C6 120.97(9)
C4 N13 H13A 121.2(9)
C4 N13 H13B 118.8(10)
H13A N13 H13B 118.8(13)
O3 N14 O4 125.19(11)
O3 N14 C5 116.91(10)
O4 N14 C5 117.90(9)
C6 N15 N16 103.17(9)
N17 N16 N15 109.56(9)
N16 N17 N18 109.89(10)
C6 N18 N17 102.89(9)
C7 N19 H19A 117.3(10)
C7 N19 H19B 121.7(10)
H19A N19 H19B 120.9(13)
C7 N20 H20A 120.3(9)
C7 N20 H20B 118.7(9)
H20A N20 H20B 120.9(12)
C7 N21 H21A 119.1(10)
C7 N21 H21B 122.8(10)
H21A N21 H21B 118.1(14)
C8 N22 H22A 121.5(9)
C8 N22 H22B 118.3(10)
H22A N22 H22B 119.8(14)
C8 N23 H23A 118.5(10)
C8 N23 H23B 118.8(10)
H23A N23 H23B 122.6(14)
C8 N24 H24A 117.8(10)
C8 N24 H24B 119.9(10)
H24A N24 H24B 121.7(14)
N4 C1 N1 127.42(10)
N4 C1 N3 123.79(10)
N1 C1 N3 108.79(9)
N2 C2 N1 118.89(9)
N2 C2 N5 119.45(9)
N1 C2 N5 121.66(9)
N6 C3 N9 114.64(9)
N6 C3 N3 122.83(9)
N9 C3 N3 122.53(9)
N13 C4 N10 127.12(10)
N13 C4 N12 124.01(10)
N10 C4 N12 108.85(9)
N11 C5 N10 118.73(10)
N11 C5 N14 119.53(10)
N10 C5 N14 121.75(9)
N15 C6 N18 114.50(10)
N15 C6 N12 123.55(10)
N18 C6 N12 121.96(10)
N20 C7 N21 120.71(10)
N20 C7 N19 120.62(10)
N21 C7 N19 118.67(10)
N24 C8 N22 120.87(11)
N24 C8 N23 120.02(11)
N22 C8 N23 119.10(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N5 1.2250(12)
O2 N5 1.2233(12)
O3 N14 1.2223(12)
O4 N14 1.2262(13)
O5 H05A 0.858(17)
O5 H05B 0.785(17)
N1 C1 1.3371(13)
N1 C2 1.3439(13)
N2 C2 1.3078(13)
N2 N3 1.3759(12)
N3 C1 1.3721(13)
N3 C3 1.4004(13)
N4 C1 1.3253(14)
N4 H4A 0.907(14)
N4 H4B 0.847(15)
N5 C2 1.4574(14)
N6 C3 1.3203(13)
N6 N7 1.3551(13)
N7 N8 1.3094(14)
N8 N9 1.3523(13)
N9 C3 1.3285(13)
N10 C4 1.3359(14)
N10 C5 1.3479(14)
N11 C5 1.3008(13)
N11 N12 1.3748(13)
N12 C4 1.3709(13)
N12 C6 1.3997(13)
N13 C4 1.3305(15)
N13 H13A 0.929(14)
N13 H13B 0.865(16)
N14 C5 1.4544(15)
N15 C6 1.3171(14)
N15 N16 1.3513(14)
N16 N17 1.3104(15)
N17 N18 1.3488(14)
N18 C6 1.3243(14)
N19 C7 1.3313(14)
N19 H19A 0.886(15)
N19 H19B 0.847(16)
N20 C7 1.3143(14)
N20 H20A 0.911(16)
N20 H20B 0.863(14)
N21 C7 1.3295(14)
N21 H21A 0.901(16)
N21 H21B 0.883(15)
N22 C8 1.3198(15)
N22 H22A 0.923(15)
N22 H22B 0.855(16)
N23 C8 1.3315(14)
N23 H23A 0.867(15)
N23 H23B 0.901(17)
N24 C8 1.3198(15)
N24 H24A 0.872(16)
N24 H24B 0.853(16)
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
C2 N2 N3 C1 0.24(11)
C2 N2 N3 C3 178.05(9)
C3 N6 N7 N8 -0.09(12)
N6 N7 N8 N9 -0.01(13)
N7 N8 N9 C3 0.10(12)
C5 N11 N12 C4 -0.28(11)
C5 N11 N12 C6 -179.06(10)
C6 N15 N16 N17 0.12(13)
N15 N16 N17 N18 -0.09(13)
N16 N17 N18 C6 0.03(12)
C2 N1 C1 N4 179.36(11)
C2 N1 C1 N3 -0.27(11)
N2 N3 C1 N4 -179.62(9)
C3 N3 C1 N4 2.78(17)
N2 N3 C1 N1 0.02(11)
C3 N3 C1 N1 -177.57(9)
N3 N2 C2 N1 -0.46(12)
N3 N2 C2 N5 179.98(9)
C1 N1 C2 N2 0.49(12)
C1 N1 C2 N5 -179.96(9)
O2 N5 C2 N2 -4.42(14)
O1 N5 C2 N2 175.82(9)
O2 N5 C2 N1 176.03(9)
O1 N5 C2 N1 -3.73(14)
N7 N6 C3 N9 0.17(12)
N7 N6 C3 N3 -178.66(9)
N8 N9 C3 N6 -0.17(12)
N8 N9 C3 N3 178.66(9)
C1 N3 C3 N6 176.82(10)
N2 N3 C3 N6 -0.55(15)
C1 N3 C3 N9 -1.91(16)
N2 N3 C3 N9 -179.28(9)
C5 N10 C4 N13 178.30(11)
C5 N10 C4 N12 0.16(11)
N11 N12 C4 N13 -178.13(10)
C6 N12 C4 N13 0.53(18)
N11 N12 C4 N10 0.07(12)
C6 N12 C4 N10 178.74(10)
N12 N11 C5 N10 0.43(12)
N12 N11 C5 N14 -178.87(9)
C4 N10 C5 N11 -0.39(13)
C4 N10 C5 N14 178.88(10)
O3 N14 C5 N11 177.42(10)
O4 N14 C5 N11 -2.26(15)
O3 N14 C5 N10 -1.85(15)
O4 N14 C5 N10 178.47(10)
N16 N15 C6 N18 -0.10(13)
N16 N15 C6 N12 179.79(10)
N17 N18 C6 N15 0.05(13)
N17 N18 C6 N12 -179.84(10)
C4 N12 C6 N15 173.54(10)
N11 N12 C6 N15 -7.92(16)
C4 N12 C6 N18 -6.58(17)
N11 N12 C6 N18 171.96(10)
