1,5-Diamino-tetra-zolium chloride.

The title compound, CH(5)N(6) (+)·Cl(-), crystallized with two indepedent 1,5-diamino-tetra-zolium cations and two independent chloride anions in the asymmetric unit. In the crystal, there are a number of N-H⋯Cl hydrogen-bonding inter-actions, 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 = 136.56

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.061

S = 1.07

1268 reflections

185 parameters

1 restraint

All H-atom parameters refined

Δρmax = 0.64 e Å−3

Δρmin = −0.17 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

CH5N6+·Cl−	F(000) = 560
Mr = 136.56	Dx = 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

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

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(Fo2) + (0.0395P)2 + 0.2133P] where P = (Fo2 + 2Fc2)/3
1268 reflections	(Δ/σ)max = 0.004
185 parameters	Δρmax = 0.64 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···Cl2iv	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···Cl2v	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···Cl2vi	0.81 (4)	2.67 (4)	3.388 (3)	148 (3)
N12—H12B···Cl1vii	0.80 (4)	2.39 (4)	3.173 (2)	171 (4)

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⋯Cl2iv	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⋯Cl2v	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⋯Cl2vi	0.81 (4)	2.67 (4)	3.388 (3)	148 (3)
N12—H12B⋯Cl1vii	0.80 (4)	2.39 (4)	3.173 (2)	171 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .