1,5-Diamino­tetra­zolium chloride

Meng, L.-Q.; Du, Z.-M.; He, C.-L.; Cong, X.-M.; Yang, S.; Zhao, L.-S.

doi:10.1107/S1600536810009633

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o984

doi:10.1107/S1600536810009633

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1,5-Diaminotetrazolium chloride

Ling-Qiao Meng,^a Zhi-Ming Du,^a ^* Chun-Lin He,^a Xiao-Min Cong,^a Shuai Yang ^a and Lin-Shuang Zhao ^a

^aState Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, People's Republic of China
^*Correspondence e-mail: duzhiming430@sohu.com

(Received 18 January 2010; accepted 15 March 2010; online 31 March 2010)

The title compound, CH₅N₆⁺·Cl⁻, crystallized with two indepedent 1,5-diaminotetrazolium cations and two independent chloride anions in the asymmetric unit. In the crystal, there are a number of N—H⋯Cl hydrogen-bonding interactions, which generate a three-dimensional network.

Related literature

For the preparation of the starting material, 1,5-diaminotetrazole, see: Galvez-Ruiz et al. (2005 ). For the preparation of 5-aminotetrazolium halogenide salts, see: Denffer et al. (2008 ) and of 1,5-diaminotetrazolium hydrochloride, see: He et al. (2009a ). For the bond distances and angles in a related structure, see: He et al. (2009b ). For van der Waals radii, see: http://biblo.chm.uri.edu/PeriodicTable/PeriodicTableoftheElements.htm .

Experimental

Crystal data

CH₅N₆⁺·Cl⁻
M_r = 136.56
Orthorhombic, P n a 2₁
a = 12.389 (3) Å
b = 6.4500 (12) Å
c = 13.305 (3) Å
V = 1063.1 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 93 K
0.43 × 0.27 × 0.10 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.778, T_max = 0.942
7927 measured reflections
1268 independent reflections
1246 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.061
S = 1.07
1268 reflections
185 parameters
1 restraint
All H-atom parameters refined
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯Cl2	0.93 (4)	2.16 (4)	3.017 (2)	154 (4)
N5—H5A⋯Cl1ⁱ	0.79 (4)	2.77 (4)	3.555 (3)	179 (6)
N5—H5B⋯Cl2ⁱⁱ	0.94 (4)	2.39 (4)	3.317 (2)	170 (3)
N6—H6A⋯Cl1ⁱⁱⁱ	0.86 (4)	2.65 (4)	3.376 (3)	142 (3)
N6—H6B⋯Cl2^iv	0.93 (4)	2.25 (4)	3.146 (2)	162 (3)
N10—H10⋯Cl1ⁱ	0.79 (4)	2.30 (4)	3.021 (2)	152 (4)
N11—H11A⋯Cl2^v	0.96 (4)	2.65 (4)	3.567 (3)	161 (3)
N11—H11B⋯Cl1	0.85 (4)	2.47 (4)	3.306 (2)	170 (3)
N12—H12A⋯Cl2^vi	0.81 (4)	2.67 (4)	3.388 (3)	148 (3)
N12—H12B⋯Cl1^vii	0.80 (4)	2.39 (4)	3.173 (2)	171 (4)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iv) x, y-1, z; (v) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (vi) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (vii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009633/su2159sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009633/su2159Isup2.hkl

checkCIF report

Comment top

The synthesis and study of nitrogen-rich energetic salts and highly energetic materials for possible military as well as civil applications has attracted considerable interest in recent years, especially the salts with tetrazole-containing compounds (Galvez-Ruiz et al., 2005; Denffer et al., 2008). The nitrogen content of 5-amniotetrazole and 1,5-diaminotetrazole, which are primary sources for preparing energetic salts, is 82.3% and 84%, respectively. Denffer et al. (2008) reported the synthesis of 5-aminotetrazolium hydrochloride and determinated its crystal structure. Our rearch group has recently reported on the synthesis of the title compound (He et al.., 2009a,b), and herein we report on its crystal structure.

The molecular structure of the title molecule is presented in Fig. 1. It crystallizes with two independent 1,5-Diaminotetrazolium cations and two independent chloride anions per asymmetric unit. The bond distances and angles are as expected for a molecule of this kind, and are similar to the corresponding distances and angles reported by (He et al., 2009a,b). The cations, excluding the N6 and N11 hydrogen atoms, are planar (maximum deviation 0.020 (2) Å).

The distance between the Cl1 anion and the plane formed by the cation ring 1, (= N1,N2,N3,N4,C1), is 0.445 (1) Å, and the perpendicular distances of this cation centroid, Cg1, to the parallel cation 2 ring planes (= N7,N8,N9,N10,C2), are 2.868 (1) Å (symmetry code: 1-x, -y, 0.5+z) and 2.922 (1) Å (symmetry code: 1-x, 1-y, 0.5+z). The distances of N2—C2 (2.864 (4) Å) and N8—C1ⁱ (2.883 (4) Å) [symmetry code (i) = 0.5+x, 0.5-y, z] are smaller than the sum of the associated van der Waals Radii (r_N + r_C = 3.25 Å), because of edge-to-face π-π interactions between the two cations. Both of the amino groups, in position 4 (N4) and position 5 (N6), form a long contact to the Cl2^- anion (N4—Cl2 = 3.017 (2) Å and N6—Cl2ⁱⁱ = 3.146 (2) Å [symmetry code (ii) = x, 1+y, z]), which is within the sum of the van der Waals radii (r_N +r_Cl = 3.30 Å).

In the crystal there are a number of N-H···Cl hydrogen bonds which result in the foamation of a three-dimensional network (Table 1).

Related literature top

For the preparation of the starting material, 1,5-diaminotetrazole, see: Galvez-Ruiz et al. (2005). For the preparation of 5-aminotetrazolium halogenide salts, see: Denffer et al. (2008) and of 1,5-diaminotetrazolium hydrochloride, see: He et al. (2009a). For the bond distances and angles in a related structure, see: He et al. (2009b). For van der Waals radii, see: http://biblo.chm.uri.edu/PeriodicTable/PeriodicTableoftheElements.htm.

Experimental top

The starting material, 1,5-diaminotetrazole, was prepared according to the literature method (Galvez-Ruiz et al., 2005). 1,5-diaminotetrazole (2.0043 g, 20.04 mmol) suspended in 40 mL of methanol, was reacted with 10 mL concentrated HCl. The reaction mixture was refluxed for 2 h and then the solvent was evaporated until precipitation occured. The concentrated solution was then placed in the refrigerator, and the white 1,5-diaminotetrazolium hydrochloride was obtained. The precipitate was filtered off and washed with water. The crude product was recrystallized from methanol (Yield: 2.4189 g, 88.6%). Crystals suitable for X-ray structure determination were obtained by slow evaporation of a solution in methanol at rt.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

1,5-Diaminotetrazolium chloride top

Crystal data top

CH₅N₆⁺·Cl⁻	F(000) = 560
M_r = 136.56	D_x = 1.706 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3581 reflections
a = 12.389 (3) Å	θ = 3.1–27.5°
b = 6.4500 (12) Å	µ = 0.61 mm⁻¹
c = 13.305 (3) Å	T = 93 K
V = 1063.1 (4) Å³	Prism, colourless
Z = 8	0.43 × 0.27 × 0.10 mm

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	1268 independent reflections
Radiation source: Rotating Anode	1246 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
Multi–scan	h = −16→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −8→8
T_min = 0.778, T_max = 0.942	l = −16→17
7927 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.025	Hydrogen site location: difference Fourier map
wR(F²) = 0.061	All H-atom parameters refined
S = 1.07	w = 1/[σ²(F_o²) + (0.0395P)² + 0.2133P] where P = (F_o² + 2F_c²)/3
1268 reflections	(Δ/σ)_max = 0.004
185 parameters	Δρ_max = 0.64 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

CH₅N₆⁺·Cl⁻	V = 1063.1 (4) Å³
M_r = 136.56	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.389 (3) Å	µ = 0.61 mm⁻¹
b = 6.4500 (12) Å	T = 93 K
c = 13.305 (3) Å	0.43 × 0.27 × 0.10 mm

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	1268 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	1246 reflections with I > 2σ(I)
T_min = 0.778, T_max = 0.942	R_int = 0.029
7927 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	1 restraint
wR(F²) = 0.061	All H-atom parameters refined
S = 1.07	Δρ_max = 0.64 e Å⁻³
1268 reflections	Δρ_min = −0.17 e Å⁻³
185 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.44089 (16)	0.1470 (3)	0.39856 (16)	0.0134 (6)
N2	0.51729 (18)	0.2805 (3)	0.36265 (19)	0.0157 (6)
N3	0.48306 (18)	0.4641 (3)	0.37753 (18)	0.0191 (7)
N4	0.38470 (18)	0.4512 (3)	0.42323 (16)	0.0170 (6)
N5	0.44793 (18)	−0.0680 (3)	0.39178 (19)	0.0174 (6)
N6	0.26869 (18)	0.1788 (3)	0.4778 (2)	0.0173 (6)
C1	0.3577 (2)	0.2537 (4)	0.4364 (2)	0.0129 (7)
N7	0.68577 (16)	0.3860 (3)	0.20486 (15)	0.0128 (6)
N8	0.76391 (17)	0.2503 (3)	0.23810 (19)	0.0154 (6)
N9	0.73281 (18)	0.0683 (3)	0.21667 (17)	0.0170 (6)
N10	0.63448 (17)	0.0824 (3)	0.17032 (17)	0.0153 (6)
N11	0.68953 (18)	0.5995 (3)	0.21790 (18)	0.0154 (6)
N12	0.51472 (17)	0.3555 (3)	0.1248 (2)	0.0167 (6)
C2	0.6038 (2)	0.2794 (4)	0.1630 (2)	0.0131 (7)
Cl1	0.93591 (4)	0.67650 (9)	0.13004 (5)	0.0168 (2)
Cl2	0.19017 (4)	0.71516 (9)	0.47049 (5)	0.0174 (2)
H4	0.342 (3)	0.565 (7)	0.438 (3)	0.048 (12)*
H5A	0.446 (3)	−0.093 (7)	0.334 (3)	0.037 (11)*
H5B	0.514 (3)	−0.104 (5)	0.422 (3)	0.031 (9)*
H6A	0.215 (3)	0.259 (6)	0.492 (3)	0.037 (10)*
H6B	0.260 (3)	0.037 (6)	0.469 (3)	0.040 (10)*
H10	0.599 (3)	−0.016 (6)	0.158 (3)	0.028 (9)*
H11A	0.677 (3)	0.623 (5)	0.288 (3)	0.024 (8)*
H11B	0.753 (3)	0.634 (5)	0.200 (2)	0.016 (7)*
H12A	0.477 (3)	0.275 (5)	0.094 (3)	0.021 (9)*
H12B	0.502 (3)	0.476 (6)	0.129 (3)	0.028 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0118 (10)	0.0145 (10)	0.0140 (10)	−0.0003 (8)	−0.0009 (8)	0.0006 (8)
N2	0.0157 (11)	0.0187 (10)	0.0126 (12)	−0.0025 (8)	0.0014 (9)	0.0005 (8)
N3	0.0194 (11)	0.0213 (12)	0.0166 (12)	−0.0018 (8)	−0.0005 (10)	−0.0002 (10)
N4	0.0165 (11)	0.0161 (10)	0.0184 (11)	0.0005 (8)	−0.0008 (9)	−0.0015 (9)
N5	0.0182 (11)	0.0141 (10)	0.0198 (12)	0.0029 (8)	0.0002 (9)	−0.0009 (9)
N6	0.0132 (9)	0.0197 (11)	0.0189 (11)	0.0007 (8)	0.0042 (10)	−0.0004 (10)
C1	0.0118 (12)	0.0175 (11)	0.0093 (12)	0.0023 (9)	−0.0028 (9)	−0.0006 (9)
N7	0.0112 (9)	0.0146 (10)	0.0125 (10)	0.0000 (8)	−0.0001 (8)	0.0008 (8)
N8	0.0115 (11)	0.0202 (10)	0.0144 (12)	0.0026 (8)	0.0003 (9)	0.0007 (8)
N9	0.0170 (11)	0.0184 (11)	0.0156 (11)	0.0014 (8)	−0.0002 (9)	−0.0001 (9)
N10	0.0124 (10)	0.0164 (10)	0.0171 (10)	−0.0023 (8)	−0.0004 (8)	−0.0027 (9)
N11	0.0126 (10)	0.0137 (10)	0.0199 (12)	−0.0020 (8)	0.0008 (9)	−0.0013 (9)
N12	0.0134 (9)	0.0170 (11)	0.0196 (11)	−0.0020 (8)	−0.0037 (10)	−0.0016 (11)
C2	0.0134 (12)	0.0165 (12)	0.0094 (12)	−0.0031 (9)	0.0028 (10)	−0.0010 (9)
Cl1	0.0114 (3)	0.0194 (3)	0.0197 (3)	−0.0004 (2)	−0.0017 (3)	0.0002 (3)
Cl2	0.0126 (3)	0.0196 (3)	0.0199 (3)	−0.0011 (2)	0.0019 (3)	−0.0003 (3)

Geometric parameters (Å, º) top

N1—N2	1.366 (3)	N7—N8	1.378 (3)
N1—N5	1.392 (3)	N7—N11	1.389 (3)
N1—C1	1.338 (3)	N7—C2	1.347 (3)
N2—N3	1.273 (3)	N8—N9	1.268 (3)
N3—N4	1.364 (3)	N9—N10	1.368 (3)
N4—C1	1.329 (3)	N10—C2	1.330 (3)
N6—C1	1.324 (3)	N12—C2	1.310 (3)
N4—H4	0.93 (4)	N10—H10	0.79 (4)
N5—H5A	0.79 (4)	N11—H11A	0.96 (4)
N5—H5B	0.94 (4)	N11—H11B	0.85 (4)
N6—H6A	0.86 (4)	N12—H12A	0.81 (4)
N6—H6B	0.93 (4)	N12—H12B	0.80 (4)

N2—N1—N5	124.2 (2)	N7—N8—N9	107.6 (2)
N2—N1—C1	109.95 (19)	N8—N9—N10	108.08 (19)
N5—N1—C1	125.8 (2)	N9—N10—C2	110.6 (2)
N1—N2—N3	107.5 (2)	C2—N10—H10	126 (3)
N2—N3—N4	108.06 (19)	N9—N10—H10	122 (3)
N3—N4—C1	110.0 (2)	N7—N11—H11B	105 (2)
N3—N4—H4	124 (2)	N7—N11—H11A	105.9 (19)
C1—N4—H4	126 (3)	H11A—N11—H11B	112 (3)
N1—N5—H5A	105 (3)	C2—N12—H12B	120 (3)
H5A—N5—H5B	113 (4)	C2—N12—H12A	116 (3)
N1—N5—H5B	106 (2)	H12A—N12—H12B	123 (4)
C1—N6—H6A	121 (3)	N4—C1—N6	127.9 (2)
C1—N6—H6B	114 (2)	N1—C1—N4	104.5 (2)
H6A—N6—H6B	122 (3)	N1—C1—N6	127.6 (2)
N8—N7—N11	124.48 (19)	N7—C2—N12	127.2 (2)
N8—N7—C2	109.76 (19)	N10—C2—N12	128.8 (2)
N11—N7—C2	125.7 (2)	N7—C2—N10	104.0 (2)

N5—N1—N2—N3	177.3 (2)	N11—N7—N8—N9	177.8 (2)
C1—N1—N2—N3	0.0 (3)	C2—N7—N8—N9	0.9 (3)
N2—N1—C1—N4	−0.2 (3)	N8—N7—C2—N10	−0.9 (3)
N2—N1—C1—N6	180.0 (3)	N8—N7—C2—N12	178.8 (3)
N5—N1—C1—N4	−177.4 (2)	N11—N7—C2—N10	−177.7 (2)
N5—N1—C1—N6	2.8 (4)	N11—N7—C2—N12	1.9 (4)
N1—N2—N3—N4	0.1 (3)	N7—N8—N9—N10	−0.5 (3)
N2—N3—N4—C1	−0.2 (3)	N8—N9—N10—C2	−0.1 (3)
N3—N4—C1—N1	0.2 (3)	N9—N10—C2—N7	0.6 (3)
N3—N4—C1—N6	−179.9 (3)	N9—N10—C2—N12	−179.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cl2	0.93 (4)	2.16 (4)	3.017 (2)	154 (4)
N5—H5A···Cl1ⁱ	0.79 (4)	2.77 (4)	3.555 (3)	179 (6)
N5—H5B···Cl2ⁱⁱ	0.94 (4)	2.39 (4)	3.317 (2)	170 (3)
N6—H6A···Cl1ⁱⁱⁱ	0.86 (4)	2.65 (4)	3.376 (3)	142 (3)
N6—H6B···Cl2^iv	0.93 (4)	2.25 (4)	3.146 (2)	162 (3)
N10—H10···Cl1ⁱ	0.79 (4)	2.30 (4)	3.021 (2)	152 (4)
N11—H11A···Cl2^v	0.96 (4)	2.65 (4)	3.567 (3)	161 (3)
N11—H11B···Cl1	0.85 (4)	2.47 (4)	3.306 (2)	170 (3)
N12—H12A···Cl2^vi	0.81 (4)	2.67 (4)	3.388 (3)	148 (3)
N12—H12B···Cl1^vii	0.80 (4)	2.39 (4)	3.173 (2)	171 (4)

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x+1/2, −y+1/2, z; (iii) −x+1, −y+1, z+1/2; (iv) x, y−1, z; (v) x+1/2, −y+3/2, z; (vi) −x+1/2, y−1/2, z−1/2; (vii) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	CH₅N₆⁺·Cl⁻
M_r	136.56
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	93
a, b, c (Å)	12.389 (3), 6.4500 (12), 13.305 (3)
V (Å³)	1063.1 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.43 × 0.27 × 0.10

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.778, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	7927, 1268, 1246
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.061, 1.07
No. of reflections	1268
No. of parameters	185
No. of restraints	1
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.17

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cl2	0.93 (4)	2.16 (4)	3.017 (2)	154 (4)
N5—H5A···Cl1ⁱ	0.79 (4)	2.77 (4)	3.555 (3)	179 (6)
N5—H5B···Cl2ⁱⁱ	0.94 (4)	2.39 (4)	3.317 (2)	170 (3)
N6—H6A···Cl1ⁱⁱⁱ	0.86 (4)	2.65 (4)	3.376 (3)	142 (3)
N6—H6B···Cl2^iv	0.93 (4)	2.25 (4)	3.146 (2)	162 (3)
N10—H10···Cl1ⁱ	0.79 (4)	2.30 (4)	3.021 (2)	152 (4)
N11—H11A···Cl2^v	0.96 (4)	2.65 (4)	3.567 (3)	161 (3)
N11—H11B···Cl1	0.85 (4)	2.47 (4)	3.306 (2)	170 (3)
N12—H12A···Cl2^vi	0.81 (4)	2.67 (4)	3.388 (3)	148 (3)
N12—H12B···Cl1^vii	0.80 (4)	2.39 (4)	3.173 (2)	171 (4)

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x+1/2, −y+1/2, z; (iii) −x+1, −y+1, z+1/2; (iv) x, y−1, z; (v) x+1/2, −y+3/2, z; (vi) −x+1/2, y−1/2, z−1/2; (vii) x−1/2, −y+3/2, z.

Acknowledgements

This work was funded by the State Key Laboratory of Explosion Science and Technology (QNKT10-09), Beijing Institute of Technology.

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