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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3297.
Published online 2010 November 24. doi:  10.1107/S1600536810047756
PMCID: PMC3011446

4-(1H-Tetra­zol-5-yl)pyridinium chloride

Abstract

In the cation of the title compound, C6H6N5 +·Cl, the tetra­zole and pyridine rings are nearly coplanar, making a dihedral angle of 5.58 (11)°. The organic cations are linked to the chloride anions via N—H(...)Cl hydrogen bonds, forming chains along [110].

Related literature

For supra­molecular self-assembly chemistry, see: Fender et al. (2002 [triangle]). For the structures of related tetra­zole derivatives, see: Fu et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3297-scheme1.jpg

Experimental

Crystal data

  • C6H6N5 +·Cl
  • M r = 183.61
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3297-efi1.jpg
  • a = 4.8552 (10) Å
  • b = 7.5862 (15) Å
  • c = 10.884 (2) Å
  • β = 92.88 (3)°
  • V = 400.36 (14) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.42 mm−1
  • T = 298 K
  • 0.30 × 0.05 × 0.05 mm

Data collection

  • Rigaku Mercury CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.910, T max = 1.000
  • 4104 measured reflections
  • 1825 independent reflections
  • 1687 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.071
  • S = 1.11
  • 1825 reflections
  • 109 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.26 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 840 Friedel pairs
  • Flack parameter: 0.07 (6)

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047756/xu5091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047756/xu5091Isup2.hkl

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

Acknowledgments

This work was supported by a start-up grant from Anyang Institute of Technology, China.

supplementary crystallographic information

Comment

In recent years there is a rapidly increasing interest in the construction of various kinds of supramolecular systems for understanding molecular self-assembly principles and for designing molecular recognition devices (Fender et al. 2002). We report here the crystal structure of the title compound, 4-(1H-tetrazol-5-yl)pyridinium chloride.

In the title compound (Fig.1), the pyridine N atom is protonated. The tetrazole and pyridine rings are nearly coplanar and only twisted from each other by a dihedral angle of 5.58 (11)°. The geometric parameters of the tetrazole rings are comparable to those in related molecules (Fu et al., 2009).

In the crystal structure, the organic cations are connected by the Cl- anions through two type of N—H···Cl hydrogen bonds, with the N···Cl distance of 3.0704 (2)Å and 3.0344 (2) Å, respectively. Those H-bonds link the ion units into a one-dimensional chain along the [1 1 0] direction (Table 1 and Fig. 2).

Experimental

4-(1H-Tetrazol-5-yl)pyridinium chloride was obtained commercially, and the single crystals were obtained from an ethanol solution.

Refinement

H atoms attached to N atoms were located in a difference Fourier map, and refined in riding mode with N–H = 0.86 Å and Uiso(H) = 1.2Ueq(N). Other H atoms were fixed geometrically and treated as riding with C–H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
Fig. 2.
Part of the crystal packing of the title compound. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Crystal data

C6H6N5+·ClF(000) = 188
Mr = 183.61Dx = 1.523 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1825 reflections
a = 4.8552 (10) Åθ = 3.3–27.5°
b = 7.5862 (15) ŵ = 0.42 mm1
c = 10.884 (2) ÅT = 298 K
β = 92.88 (3)°Block, colorless
V = 400.36 (14) Å30.30 × 0.05 × 0.05 mm
Z = 2

Data collection

Rigaku Mercury CCD diffractometer1825 independent reflections
Radiation source: fine-focus sealed tube1687 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.3°
[var phi] and ω scanh = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −9→9
Tmin = 0.910, Tmax = 1.000l = −14→14
4104 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.071w = 1/[σ2(Fo2) + (0.029P)2 + 0.0441P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
1825 reflectionsΔρmax = 0.16 e Å3
109 parametersΔρmin = −0.26 e Å3
1 restraintAbsolute structure: Flack (1983), 840 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.07 (6)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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 > σ(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)

xyzUiso*/Ueq
N30.6191 (4)0.2346 (2)0.94401 (17)0.0448 (5)
C40.5024 (4)0.7071 (3)0.67942 (18)0.0354 (4)
H40.36110.64170.64070.043*
N40.4093 (4)0.2114 (2)0.86534 (18)0.0426 (4)
N50.3900 (3)0.3586 (2)0.79785 (15)0.0356 (4)
H5A0.26780.37860.73960.043*
C60.5897 (4)0.4690 (2)0.83517 (16)0.0290 (4)
N10.7754 (3)0.9626 (2)0.69060 (16)0.0390 (4)
H1A0.81751.06320.66040.047*
C20.8551 (4)0.7442 (3)0.83953 (19)0.0360 (5)
H20.95280.70300.90940.043*
N20.7348 (4)0.3944 (2)0.92686 (16)0.0389 (4)
C10.9159 (5)0.9050 (3)0.7917 (2)0.0400 (5)
H11.05410.97430.82920.048*
C50.5724 (4)0.8690 (3)0.63512 (18)0.0401 (5)
H50.47750.91420.56570.048*
C30.6467 (4)0.6419 (3)0.78358 (16)0.0293 (4)
Cl10.95294 (9)0.32109 (6)0.59025 (4)0.04239 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N30.0493 (10)0.0393 (10)0.0450 (10)−0.0036 (9)−0.0050 (8)0.0062 (9)
C40.0335 (10)0.0399 (11)0.0322 (10)−0.0090 (9)−0.0049 (8)−0.0024 (8)
N40.0449 (10)0.0337 (10)0.0484 (10)−0.0080 (8)−0.0059 (8)0.0056 (8)
N50.0347 (8)0.0346 (11)0.0366 (8)−0.0080 (7)−0.0062 (7)0.0042 (7)
C60.0258 (9)0.0326 (10)0.0286 (8)−0.0027 (7)−0.0009 (7)−0.0047 (7)
N10.0460 (10)0.0302 (9)0.0412 (9)−0.0088 (8)0.0058 (8)0.0008 (7)
C20.0338 (10)0.0387 (11)0.0345 (10)−0.0071 (9)−0.0083 (8)−0.0026 (9)
N20.0416 (9)0.0362 (9)0.0377 (9)−0.0024 (8)−0.0082 (7)0.0023 (7)
C10.0381 (11)0.0380 (11)0.0436 (12)−0.0112 (9)−0.0019 (9)−0.0067 (10)
C50.0442 (11)0.0419 (13)0.0338 (10)−0.0059 (9)−0.0021 (9)0.0036 (8)
C30.0296 (9)0.0299 (9)0.0285 (9)−0.0029 (7)0.0028 (7)−0.0042 (7)
Cl10.0465 (3)0.0433 (3)0.0362 (2)−0.0112 (3)−0.00936 (18)0.0070 (2)

Geometric parameters (Å, °)

N3—N41.309 (3)C6—C31.459 (3)
N3—N21.353 (2)N1—C51.334 (3)
C4—C51.369 (3)N1—C11.338 (3)
C4—C31.393 (3)N1—H1A0.8600
C4—H40.9300C2—C11.365 (3)
N4—N51.337 (2)C2—C31.391 (3)
N5—C61.330 (2)C2—H20.9300
N5—H5A0.8600C1—H10.9300
C6—N21.320 (2)C5—H50.9300
N4—N3—N2110.18 (18)C1—C2—C3119.9 (2)
C5—C4—C3118.78 (19)C1—C2—H2120.0
C5—C4—H4120.6C3—C2—H2120.0
C3—C4—H4120.6C6—N2—N3106.21 (16)
N3—N4—N5106.13 (17)N1—C1—C2119.6 (2)
C6—N5—N4109.17 (15)N1—C1—H1120.2
C6—N5—H5A125.4C2—C1—H1120.2
N4—N5—H5A125.4N1—C5—C4120.6 (2)
N2—C6—N5108.31 (17)N1—C5—H5119.7
N2—C6—C3124.90 (17)C4—C5—H5119.7
N5—C6—C3126.77 (16)C2—C3—C4118.91 (18)
C5—N1—C1122.22 (18)C2—C3—C6118.76 (17)
C5—N1—H1A118.9C4—C3—C6122.33 (17)
C1—N1—H1A118.9

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1i0.862.213.0704 (18)176
N5—H5A···Cl1ii0.862.223.0344 (18)159

Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5091).

References

  • Fender, N. S., Kahwa, I. A. & Fronczek, F. R. (2002). J. Solid State Chem.163, 286–293.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Fu, D.-W., Ge, J.-Z., Dai, J., Ye, H.-Y. & Qu, Z.-R. (2009). Inorg. Chem. Commun.12, 994–997.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography