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ISSN: 2056-9890

2-[(2H-Tetra­zol-2-yl)meth­yl]benzo­nitrile

aResearch Centre for Rare Earth and Micro/Nano Functional Materials, Nan Chang University, Nan Chang 330047, People's Republic of China
*Correspondence e-mail: hbii@yahoo.cn

(Received 19 November 2007; accepted 29 November 2007; online 6 December 2007)

The title compound, C9H7N5, is non-planar with a dihedral angle between the substituted benzene and tetra­zole rings of 71.13 (9)°. Molecules are connected in centrosymmetric dimers by weak C—H⋯N inter­actions [C⋯N is 3.548 (5) Å]; these are the only interactions of significance in the crystal structure.

Related literature

For the applications of tetra­zole derivatives as ligands in coordination chemistry, see: Huang et al. (2006[Huang, X.-H., Sheng, T.-L., Xiang, S.-C., Fu, R.-B., Hu, S.-M., Li, Y.-M. & Wu, X.-T. (2006). Inorg. Chem. Commun. 9, 1304-1307.]); Fu & Zhao (2007[Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, m1955.]); Hu et al. (2007[Hu, B., Xu, X.-B., Li, Y.-X. & Ye, H.-Y. (2007). Acta Cryst. E63, m2698.]).

[Scheme 1]

Experimental

Crystal data
  • C9H7N5

  • Mr = 185.20

  • Monoclinic, P 21 /c

  • a = 12.213 (11) Å

  • b = 13.724 (13) Å

  • c = 5.549 (5) Å

  • β = 102.24 (2)°

  • V = 909.0 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 (2) K

  • 0.22 × 0.15 × 0.1 mm

Data collection
  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Version 1.4.0. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.97, Tmax = 1.00 (expected range = 0.961–0.991)

  • 6450 measured reflections

  • 1493 independent reflections

  • 1185 reflections with I > 2σ(I)

  • Rint = 0.098

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.187

  • S = 1.05

  • 1493 reflections

  • 127 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Version 1.4.0. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL/PC (Sheldrick, 1999[Sheldrick, G. M. (1999). SHELXTL/PC. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL/PC.

Supporting information


Comment top

Ligands containing tetrazole groups could serve as potential multidentate or bridging building blocks for the construction of polymeric structures as they possess several possible donor N atoms (Huang et al.,2006). The tetrazole functional group has found a wide range of applications in coordination chemistry as ligand in coordination chemistry, in medicinal chemistry as a metabolically stable surrogate for a carboxylic acid group, and in materials science as high density energy materials (Fu et al., 2007). We originally attempted to synthesize complexes featuring Mn metal chains by reaction of the MnCl2.4H2O with 2-(bromomethyl)benzonitrile and 2H-tetrazole ligand. Unfortunately, we obtained only the title compound and we report herein the crystal structure of the title compound, 2-[(2H-tetrazol-2-yl)methyl]benzonitrile (I) (Fig.1).

In the title molecule the bond lengths and angles are in normal ranges (Hu et al., 2007). The phenyl ring is twisted away from coplanarity with the tetrazole ring and forms dihedral angles of 71.13 (9)°.

Related literature top

For the applications of tetrazole derivatives as ligands in coordination chemistry, see: Huang et al. (2006); Fu & Zhao (2007); Hu et al., (2007).

Experimental top

A mixture of 2-(bromomethyl)benzonitrile (39.2 mg, 0.2 mmol), 2H-tetrazole(14 mg, 0.2 mmol), KOH(11.2 mg, 0.2 mmol), MnCl2.4H2O (20 mg, 0.1 mmol), 2 ml me thanol and 0.3 ml H2O were placed in a thick Pyrex tube (ca 20 cm in length). The tube was frozen with liquid N2, evacuated under vacuum and sealed by heat. The tube was then placed into oven at 75 °C for 3 days to give colorless block crystals of the title complex.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded, with d(C—H) = 0.93 and d(N—H) = 0.90Å and Uiso(H) = 1.2Ueq(C or N). In the absence of significant anomalous scattering effects, Friedel pairs were merged.

Structure description top

Ligands containing tetrazole groups could serve as potential multidentate or bridging building blocks for the construction of polymeric structures as they possess several possible donor N atoms (Huang et al.,2006). The tetrazole functional group has found a wide range of applications in coordination chemistry as ligand in coordination chemistry, in medicinal chemistry as a metabolically stable surrogate for a carboxylic acid group, and in materials science as high density energy materials (Fu et al., 2007). We originally attempted to synthesize complexes featuring Mn metal chains by reaction of the MnCl2.4H2O with 2-(bromomethyl)benzonitrile and 2H-tetrazole ligand. Unfortunately, we obtained only the title compound and we report herein the crystal structure of the title compound, 2-[(2H-tetrazol-2-yl)methyl]benzonitrile (I) (Fig.1).

In the title molecule the bond lengths and angles are in normal ranges (Hu et al., 2007). The phenyl ring is twisted away from coplanarity with the tetrazole ring and forms dihedral angles of 71.13 (9)°.

For the applications of tetrazole derivatives as ligands in coordination chemistry, see: Huang et al. (2006); Fu & Zhao (2007); Hu et al., (2007).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 1999).

Figures top
[Figure 1] Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
2-[(2H-Tetrazol-2-yl)methyl]benzonitrile top
Crystal data top
C9H7N5F(000) = 384
Mr = 185.20Dx = 1.353 Mg m3
Monoclinic, P21/cMelting point: 356 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.213 (11) ÅCell parameters from 7893 reflections
b = 13.724 (13) Åθ = 3.4–27.5°
c = 5.549 (5) ŵ = 0.09 mm1
β = 102.24 (2)°T = 293 K
V = 909.0 (15) Å3Block, colorless
Z = 40.22 × 0.15 × 0.1 mm
Data collection top
Rigaku SCXmini
diffractometer
1493 independent reflections
Radiation source: fine-focus sealed tube1185 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.098
Detector resolution: 13.6612 pixels mm-1θmax = 25.0°, θmin = 3.4°
ω scansh = 1414
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1616
Tmin = 0.97, Tmax = 1.00l = 66
6450 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1044P)2]
where P = (Fo2 + 2Fc2)/3
1493 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C9H7N5V = 909.0 (15) Å3
Mr = 185.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.213 (11) ŵ = 0.09 mm1
b = 13.724 (13) ÅT = 293 K
c = 5.549 (5) Å0.22 × 0.15 × 0.1 mm
β = 102.24 (2)°
Data collection top
Rigaku SCXmini
diffractometer
1493 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1185 reflections with I > 2σ(I)
Tmin = 0.97, Tmax = 1.00Rint = 0.098
6450 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.187H-atom parameters constrained
S = 1.05Δρmax = 0.15 e Å3
1493 reflectionsΔρmin = 0.16 e Å3
127 parameters
Special details top

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 > 2σ(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
xyzUiso*/Ueq
C10.15609 (14)0.47882 (13)0.0640 (4)0.0489 (6)
C20.10185 (16)0.56933 (17)0.1044 (5)0.0666 (7)
H2A0.05060.58140.25100.080*
C30.1252 (2)0.64046 (15)0.0756 (6)0.0744 (9)
H3A0.08900.70040.05050.089*
C40.2020 (2)0.62302 (15)0.2925 (6)0.0710 (7)
H4A0.21810.67160.41170.085*
C50.25499 (16)0.53387 (14)0.3331 (4)0.0569 (6)
H5A0.30590.52260.48060.068*
C60.23325 (13)0.46083 (12)0.1566 (3)0.0432 (5)
C70.12946 (15)0.40397 (17)0.2487 (4)0.0569 (6)
C80.29305 (15)0.36441 (12)0.2059 (4)0.0465 (6)
H8A0.30780.35070.38130.056*
H8B0.24540.31300.12120.056*
C90.51482 (17)0.36439 (14)0.0975 (4)0.0587 (6)
H9A0.54800.36080.23340.070*
N10.10778 (17)0.34457 (16)0.3975 (4)0.0754 (7)
N20.39950 (12)0.36529 (9)0.1217 (3)0.0433 (5)
N30.49695 (14)0.37893 (13)0.2704 (3)0.0630 (6)
N40.57203 (15)0.37836 (15)0.1306 (4)0.0678 (6)
N50.40562 (14)0.35604 (12)0.1126 (3)0.0552 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0428 (10)0.0547 (11)0.0522 (12)0.0003 (8)0.0167 (9)0.0067 (8)
C20.0547 (13)0.0700 (14)0.0783 (15)0.0112 (10)0.0212 (12)0.0261 (13)
C30.0700 (16)0.0464 (12)0.119 (2)0.0109 (10)0.0484 (17)0.0138 (13)
C40.0750 (16)0.0529 (12)0.0948 (19)0.0049 (10)0.0396 (15)0.0139 (12)
C50.0562 (13)0.0592 (12)0.0584 (13)0.0083 (9)0.0191 (11)0.0097 (9)
C60.0407 (10)0.0452 (9)0.0463 (11)0.0036 (7)0.0153 (9)0.0037 (8)
C70.0463 (11)0.0757 (14)0.0472 (12)0.0005 (10)0.0066 (10)0.0048 (10)
C80.0457 (11)0.0477 (11)0.0480 (11)0.0004 (7)0.0139 (9)0.0058 (8)
C90.0521 (13)0.0689 (14)0.0585 (14)0.0083 (9)0.0196 (11)0.0109 (10)
N10.0696 (13)0.0911 (15)0.0605 (13)0.0000 (10)0.0024 (11)0.0086 (11)
N20.0433 (9)0.0448 (9)0.0411 (9)0.0003 (6)0.0072 (7)0.0010 (6)
N30.0460 (11)0.0896 (13)0.0505 (11)0.0045 (8)0.0034 (9)0.0062 (9)
N40.0452 (10)0.0904 (13)0.0682 (13)0.0071 (8)0.0133 (10)0.0068 (10)
N50.0523 (11)0.0683 (11)0.0455 (10)0.0045 (7)0.0115 (8)0.0056 (8)
Geometric parameters (Å, º) top
C1—C61.399 (3)C6—C81.508 (3)
C1—C21.403 (3)C7—N11.150 (3)
C1—C71.439 (3)C8—N21.472 (3)
C2—C31.382 (4)C8—H8A0.9700
C2—H2A0.9300C8—H8B0.9700
C3—C41.381 (4)C9—N51.323 (3)
C3—H3A0.9300C9—N41.324 (3)
C4—C51.380 (3)C9—H9A0.9300
C4—H4A0.9300N2—N31.310 (2)
C5—C61.387 (3)N2—N51.324 (3)
C5—H5A0.9300N3—N41.321 (3)
C6—C1—C2120.24 (19)C1—C6—C8121.60 (17)
C6—C1—C7120.39 (17)N1—C7—C1179.5 (2)
C2—C1—C7119.35 (19)N2—C8—C6111.20 (14)
C3—C2—C1119.4 (2)N2—C8—H8A109.4
C3—C2—H2A120.3C6—C8—H8A109.4
C1—C2—H2A120.3N2—C8—H8B109.4
C4—C3—C2120.3 (2)C6—C8—H8B109.4
C4—C3—H3A119.8H8A—C8—H8B108.0
C2—C3—H3A119.8N5—C9—N4113.2 (2)
C5—C4—C3120.3 (2)N5—C9—H9A123.4
C5—C4—H4A119.9N4—C9—H9A123.4
C3—C4—H4A119.9N3—N2—N5113.55 (16)
C4—C5—C6120.8 (2)N3—N2—C8123.14 (17)
C4—C5—H5A119.6N5—N2—C8123.26 (16)
C6—C5—H5A119.6N2—N3—N4106.27 (18)
C5—C6—C1118.86 (17)N3—N4—C9105.73 (18)
C5—C6—C8119.54 (18)C9—N5—N2101.27 (16)
C6—C1—C2—C30.1 (3)C5—C6—C8—N289.3 (2)
C7—C1—C2—C3178.34 (18)C1—C6—C8—N290.6 (2)
C1—C2—C3—C40.6 (3)C6—C8—N2—N399.7 (2)
C2—C3—C4—C50.9 (4)C6—C8—N2—N577.7 (2)
C3—C4—C5—C60.8 (3)N5—N2—N3—N40.3 (2)
C4—C5—C6—C10.2 (3)C8—N2—N3—N4177.94 (15)
C4—C5—C6—C8179.64 (17)N2—N3—N4—C90.1 (2)
C2—C1—C6—C50.1 (3)N5—C9—N4—N30.1 (3)
C7—C1—C6—C5178.51 (17)N4—C9—N5—N20.3 (2)
C2—C1—C6—C8179.96 (16)N3—N2—N5—C90.38 (19)
C7—C1—C6—C81.6 (3)C8—N2—N5—C9178.00 (14)

Experimental details

Crystal data
Chemical formulaC9H7N5
Mr185.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.213 (11), 13.724 (13), 5.549 (5)
β (°) 102.24 (2)
V3)909.0 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.22 × 0.15 × 0.1
Data collection
DiffractometerRigaku SCXmini
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.97, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
6450, 1493, 1185
Rint0.098
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.187, 1.05
No. of reflections1493
No. of parameters127
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.16

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1999).

 

Acknowledgements

This work was supported by a JiangXi Provincial Natural Science Foundation grant to Professor Yong-Xiu Li.

References

First citationFu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, m1955.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHuang, X.-H., Sheng, T.-L., Xiang, S.-C., Fu, R.-B., Hu, S.-M., Li, Y.-M. & Wu, X.-T. (2006). Inorg. Chem. Commun. 9, 1304–1307.  Web of Science CSD CrossRef CAS Google Scholar
First citationHu, B., Xu, X.-B., Li, Y.-X. & Ye, H.-Y. (2007). Acta Cryst. E63, m2698.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (2005). CrystalClear. Version 1.4.0. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (1999). SHELXTL/PC. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar

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ISSN: 2056-9890
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