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Acta Cryst. (2008). E64, o975    [ doi:10.1107/S1600536808010969 ]

4-[(1H-Benzotriazol-1-yl)methyl]benzonitrile

W.-X. Wang and H. Zhao

Abstract top

In the molecule of the title compound, C14H10N4, which was prepared by reaction of benzotriazole with 4-(bromomethyl)benzonitrile in alkaline solution, the dihedral angle between the benzotriazole and benzene ring systems is 69.03 (6)°.

Comment top

Benzotriazole and its derivatives comprise an important class of corrosion inhibitors, typically used as trace additives in industrial chemical mixtures, such as coolants, cutting fluids and hydraulic fluid (Pillard et al., 2001). These derivatives are also used as inhibitors of Acanthamoeba castellanii (Kopanska et al., 2004) and are responsible for toxicity to bacteria (Gruden et al., 2001). In this paper the crystal structure of the title compound is reported.

In the title compound, bond lengths and angles observed in the benzotriazole ring system are comparable with those reported in other benzotriazole compounds (Selvanayagam et al., 2002). The dihedral angle between benzotriazole and benzene rings is 69.03 (6)°. The crystal structure is stabilized only by van der Waals contacts.

Related literature top

For the application of benzotriazole compounds in industry, see: Pillard et al. (2001); Kopanska et al. (2004); Gruden et al. (2001). For the structure of a related compound, see: Selvanayagam et al. (2002).

Experimental top

A mixture of benzotriazole (0.01 mol) and KOH (0.56 g) in methanol (20 ml) was stirred for 10 min. 4-(Bromomethyl)benzonitrile (0.01 mol) was then added and the solution refluxed for 24 h. After completion of the reaction, the reaction mixture was evaporated under vacuum. Yellow crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution after 3 days.

Refinement top

All H atoms were calculated geometrically and were refined using the riding-model approximation, with C—H =0.93-0.87 Å and with Uiso(H) = 1.2Ueq (C).

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
4-[(1H-Benzotriazol-1-yl)methyl]benzonitrile top
Crystal data top
C14H10N4F000 = 488
Mr = 234.26Dx = 1.304 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2264 reflections
a = 8.1912 (13) Åθ = 3.0–27.4º
b = 19.0520 (9) ŵ = 0.08 mm−1
c = 8.6610 (6) ÅT = 293 (2) K
β = 118.0390 (10)ºBlock, yellow
V = 1193.0 (2) Å30.50 × 0.40 × 0.40 mm
Z = 4
Data collection top
Rigaku Mercury2
diffractometer		2715 independent reflections
Radiation source: fine-focus sealed tube1903 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.0º
CCD Profile fitting scansh = −10→10
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −24→24
Tmin = 0.960, Tmax = 0.969l = −11→11
11866 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.182  w = 1/[σ2(Fo2) + (0.0763P)2 + 0.2728P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
2715 reflectionsΔρmax = 0.34 e Å−3
163 parametersΔρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C14H10N4V = 1193.0 (2) Å3
Mr = 234.26Z = 4
Monoclinic, P21/nMo Kα
a = 8.1912 (13) ŵ = 0.08 mm−1
b = 19.0520 (9) ÅT = 293 (2) K
c = 8.6610 (6) Å0.50 × 0.40 × 0.40 mm
β = 118.0390 (10)º
Data collection top
Rigaku Mercury2
diffractometer		2715 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		1903 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.969Rint = 0.047
11866 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067163 parameters
wR(F2) = 0.182H-atom parameters constrained
S = 1.09Δρmax = 0.34 e Å−3
2715 reflectionsΔρmin = −0.17 e Å−3
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 > 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) top
xyzUiso*/Ueq
C10.7006 (4)0.10232 (14)0.9067 (4)0.0662 (7)
H1A0.68910.14960.87690.079*
C20.8443 (4)0.07658 (15)1.0621 (4)0.0714 (7)
H2B0.93200.10811.13800.086*
C30.8630 (4)0.00549 (15)1.1096 (4)0.0706 (7)
C40.7387 (4)−0.04391 (14)1.0033 (4)0.0674 (7)
H4A0.7493−0.09111.03440.081*
C50.5915 (3)−0.01855 (12)0.8418 (3)0.0554 (6)
C60.5771 (3)0.05233 (12)0.8006 (3)0.0546 (6)
C70.3403 (4)0.11817 (13)0.5272 (3)0.0631 (6)
H7A0.27900.10330.40580.076*
H7B0.43720.15100.54200.076*
C80.2010 (3)0.15545 (12)0.5681 (3)0.0513 (5)
C90.2298 (3)0.22412 (12)0.6302 (3)0.0626 (6)
H9A0.33790.24740.65040.075*
C100.0989 (3)0.25833 (13)0.6624 (3)0.0616 (6)
H10A0.11820.30440.70260.074*
C11−0.0614 (3)0.22289 (11)0.6339 (3)0.0515 (5)
C12−0.0901 (3)0.15394 (12)0.5744 (3)0.0583 (6)
H12A−0.19670.13020.55660.070*
C130.0408 (3)0.12081 (12)0.5417 (3)0.0574 (6)
H13A0.02120.07470.50150.069*
C14−0.2037 (4)0.25735 (12)0.6617 (3)0.0621 (6)
N10.4254 (3)0.05596 (10)0.6402 (3)0.0574 (5)
N20.3499 (3)−0.00893 (11)0.5862 (3)0.0684 (6)
N30.4492 (3)−0.05515 (11)0.7082 (3)0.0688 (6)
N4−0.3207 (3)0.28251 (13)0.6795 (4)0.0841 (8)
H3B0.9617−0.00851.21510.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0730 (16)0.0558 (14)0.0776 (18)−0.0081 (12)0.0417 (14)−0.0063 (12)
C20.0659 (16)0.0753 (18)0.0646 (17)−0.0119 (13)0.0238 (13)−0.0063 (13)
C30.0653 (16)0.0776 (18)0.0631 (16)−0.0004 (13)0.0253 (13)−0.0002 (13)
C40.0726 (17)0.0598 (15)0.0774 (18)0.0070 (12)0.0417 (15)0.0072 (13)
C50.0539 (13)0.0533 (13)0.0677 (15)−0.0040 (10)0.0358 (12)−0.0103 (11)
C60.0604 (14)0.0511 (12)0.0641 (14)0.0022 (10)0.0390 (12)−0.0023 (10)
C70.0645 (15)0.0679 (15)0.0641 (15)0.0104 (12)0.0361 (12)0.0075 (12)
C80.0492 (12)0.0554 (13)0.0497 (12)0.0039 (9)0.0235 (10)0.0039 (10)
C90.0508 (13)0.0606 (15)0.0791 (17)−0.0085 (10)0.0327 (12)−0.0035 (12)
C100.0604 (14)0.0509 (13)0.0748 (16)−0.0079 (11)0.0328 (12)−0.0098 (11)
C110.0509 (12)0.0520 (12)0.0526 (13)0.0003 (9)0.0252 (10)−0.0016 (10)
C120.0527 (13)0.0531 (13)0.0713 (15)−0.0084 (10)0.0310 (12)−0.0083 (11)
C130.0583 (14)0.0478 (12)0.0672 (15)−0.0029 (10)0.0303 (12)−0.0084 (10)
C140.0659 (15)0.0530 (13)0.0762 (16)−0.0044 (11)0.0408 (13)−0.0065 (12)
N10.0533 (11)0.0651 (12)0.0564 (12)0.0047 (9)0.0279 (9)−0.0029 (9)
N20.0658 (13)0.0603 (13)0.0782 (15)0.0012 (10)0.0330 (11)−0.0047 (11)
N30.0681 (13)0.0547 (12)0.0851 (15)−0.0019 (10)0.0373 (12)−0.0069 (11)
N40.0786 (16)0.0733 (15)0.119 (2)−0.0010 (12)0.0622 (16)−0.0153 (14)
Geometric parameters (Å, °) top
C1—C61.379 (3)C7—H7B0.9700
C1—C21.396 (4)C8—C131.388 (3)
C1—H1A0.9301C8—C91.392 (3)
C2—C31.403 (4)C9—C101.391 (3)
C2—H2B0.9300C9—H9A0.9299
C3—C41.374 (4)C10—C111.391 (3)
C3—H3B0.9299C10—H10A0.9300
C4—C51.435 (4)C11—C121.390 (3)
C4—H4A0.9300C11—C141.453 (3)
C5—N31.384 (3)C12—C131.383 (3)
C5—C61.387 (3)C12—H12A0.9299
C6—N11.362 (3)C13—H13A0.9300
C7—N11.486 (3)C14—N41.145 (3)
C7—C81.521 (3)N1—N21.363 (3)
C7—H7A0.9700N2—N31.321 (3)
C6—C1—C2114.9 (2)C13—C8—C9119.1 (2)
C6—C1—H1A122.5C13—C8—C7119.6 (2)
C2—C1—H1A122.5C9—C8—C7121.3 (2)
C1—C2—C3123.2 (2)C10—C9—C8120.7 (2)
C1—C2—H2B118.4C10—C9—H9A119.6
C3—C2—H2B118.4C8—C9—H9A119.6
C4—C3—C2121.4 (2)C11—C10—C9119.3 (2)
C4—C3—H3B119.4C11—C10—H10A120.4
C2—C3—H3B119.3C9—C10—H10A120.4
C3—C4—C5116.2 (2)C12—C11—C10120.4 (2)
C3—C4—H4A121.9C12—C11—C14118.6 (2)
C5—C4—H4A121.9C10—C11—C14121.0 (2)
N3—C5—C6109.8 (2)C13—C12—C11119.7 (2)
N3—C5—C4129.6 (2)C13—C12—H12A120.2
C6—C5—C4120.6 (2)C11—C12—H12A120.2
N1—C6—C1132.6 (2)C12—C13—C8120.8 (2)
N1—C6—C5103.8 (2)C12—C13—H13A119.6
C1—C6—C5123.6 (2)C8—C13—H13A119.6
N1—C7—C8112.97 (18)N4—C14—C11177.3 (3)
N1—C7—H7A109.0C6—N1—N2110.69 (19)
C8—C7—H7A109.0C6—N1—C7129.3 (2)
N1—C7—H7B109.0N2—N1—C7120.0 (2)
C8—C7—H7B109.0N3—N2—N1108.7 (2)
H7A—C7—H7B107.8N2—N3—C5107.0 (2)
Acknowledgements top

This work was supported by a Start-up Grant from SEU to XRG

but XRG is not an author?.

references
References top

Gruden, C. L., Dow, S. M. & Hernandez, M. T. (2001). Water Environ. Res. 73, 72–79.

Kopanska, K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. & Bretner, M. (2004). Bioorg. Med. Chem. 12, 2617–2624.

Pillard, D. A., Cornell, J. S., Dufresne, D. L. & Hernandez, M. T. (2001). Water Res. 35, 557–560.

Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.

Selvanayagam, S., Rajakannan, V., Velmurugan, D., Dhanasekaran, M., Rajakumar, P. & Moon, J.-K. (2002). Acta Cryst. E58, o1190–o1192.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.