2-(4-Bromo-1H-indol-3-yl)acetonitrile

In the title compound, C10H7BrN2, the non-H atoms, except the N atom of the acetonitrile group and the C atom bonded to it, lie in the least-squares plane defined by the atoms of the indole ring system (r.m.s deviation = 0.019 Å), with the N and C atom of the cyano group displaced by 2.278 (1) and 1.289 (1) Å, respectively, out of that plane. In the crystal, N—H⋯N hydrogen bonds link the molecules into a C(7) chain along [100].

In the title compound, C 10 H 7 BrN 2 , the non-H atoms, except the N atom of the acetonitrile group and the C atom bonded to it, lie in the least-squares plane defined by the atoms of the indole ring system (r.m.s deviation = 0.019 Å ), with the N and C atom of the cyano group displaced by 2.278 (1) and 1.289 (1) Å , respectively, out of that plane. In the crystal, N-HÁ Á ÁN hydrogen bonds link the molecules into a C(7) chain along [100].
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2041).

Comment
The derivatives of halo indole present in several natural products (Walker et al., 2009) are also excellent intermediates for the synthesis of many biological active compounds (Giraud et al., 2011;Hendrickson & Wang, 2004) . As part of our interest in these materials, we report the crystal structure of the title compound.
The molecular structure of the title compound is shown in Fig. 1. The non-H atoms, except the nitrogen of the acetonitrile moiety and the carbon atom bonded to it, are lying in the least-squares plane defined by the atoms of the indole ring system (r.m.s deviation= 0.019 Å ), with the nitrogen and carbon of the cyano moiety shifted by 2.278 (1) and 1.289 (1) Å, respectively, out of that plane.

Experimental
The title compound was obtained commercially from ChemFuture PharmaTech, Ltd (Nanjing, Jiangsu). Crystals suitable for X-ray diffraction were obtained by slow evaporation from a methanol solution.

Refinement
All H atoms attached to C atoms and N atoms were fixed geometrically and treated as riding with C-H = 0.93 Å (CH), C-H = 0.97 Å (CH 2 ), and N-H = 0.86 Å with U iso (H) = 1.2U eq . Fig. 1 Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.