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

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-H⋯N hydrogen bonds link the mol-ecules into a C(7) chain along [100].

Related literature

For natural products with a bromo indole moiety, see: Walker et al. (2009 ▶). For the use of 4-bromo indole derivatives in the synthesis of biologically active compounds, see: Hendrickson & Wang (2004 ▶); Giraud et al. (2011 ▶). For the structures of related halo indoles, see: Kunzer & Wendt (2011 ▶).

Experimental

Crystal data

C10H7BrN2

M = 235.09

Monoclinic,

a = 8.3971 (17) Å

b = 11.237 (2) Å

c = 9.979 (2) Å

β = 104.82 (3)°

V = 910.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.46 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.983, T max = 0.983

9047 measured reflections

2082 independent reflections

1489 reflections with I > 2σ(I)

R int = 0.115

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.188

S = 1.09

2082 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −1.84 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); 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: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054936/lr2041sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054936/lr2041Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054936/lr2041Isup3.cml

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

C10H7BrN2	F(000) = 464
Mr = 235.09	Dx = 1.715 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2082 reflections
a = 8.3971 (17) Å	θ = 3.1–27.5°
b = 11.237 (2) Å	µ = 4.46 mm−1
c = 9.979 (2) Å	T = 293 K
β = 104.82 (3)°	Prism, colourless
V = 910.2 (3) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2082 independent reflections
Radiation source: fine-focus sealed tube	1489 reflections with I > 2σ(I)
graphite	Rint = 0.115
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
Tmin = 0.983, Tmax = 0.983	l = −12→12
9047 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0915P)2] where P = (Fo2 + 2Fc2)/3
2082 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −1.84 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.72608 (9)	1.02919 (6)	0.23625 (7)	0.0565 (3)
C10	0.9402 (7)	0.9743 (4)	0.2351 (5)	0.0344 (12)
N1	1.1261 (6)	0.7932 (4)	0.0298 (5)	0.0433 (11)
H1A	1.2109	0.7600	0.0124	0.052*
C5	0.9637 (6)	0.8989 (4)	0.1306 (5)	0.0285 (10)
C2	0.8646 (6)	0.8483 (4)	0.0068 (5)	0.0341 (11)
C9	1.0709 (8)	1.0096 (4)	0.3397 (6)	0.0447 (14)
H9A	1.0531	1.0623	0.4063	0.054*
C6	1.1290 (6)	0.8616 (4)	0.1422 (5)	0.0333 (11)
C8	1.2297 (8)	0.9690 (5)	0.3493 (7)	0.0520 (15)
H8A	1.3158	0.9924	0.4234	0.062*
C1	0.9703 (8)	0.7850 (5)	−0.0511 (6)	0.0410 (13)
H1B	0.9393	0.7426	−0.1338	0.049*
C3	0.6815 (6)	0.8582 (5)	−0.0559 (5)	0.0439 (13)
H3A	0.6489	0.9410	−0.0547	0.053*
H3B	0.6565	0.8326	−0.1519	0.053*
C4	0.5863 (7)	0.7872 (5)	0.0176 (6)	0.0444 (13)
N2	0.5110 (7)	0.7337 (5)	0.0738 (6)	0.0608 (14)
C7	1.2599 (7)	0.8940 (6)	0.2491 (5)	0.0490 (15)
H7A	1.3656	0.8664	0.2540	0.059*

	U11	U22	U33	U12	U13	U23
Br1	0.0551 (5)	0.0581 (5)	0.0607 (5)	0.0174 (3)	0.0226 (4)	−0.0069 (3)
C10	0.038 (3)	0.033 (3)	0.035 (3)	0.004 (2)	0.014 (2)	0.007 (2)
N1	0.047 (3)	0.040 (2)	0.052 (3)	0.008 (2)	0.029 (3)	0.0010 (19)
C5	0.033 (3)	0.024 (2)	0.031 (2)	0.0024 (17)	0.010 (2)	0.0062 (17)
C2	0.039 (3)	0.034 (3)	0.029 (2)	−0.006 (2)	0.008 (2)	0.0037 (19)
C9	0.062 (4)	0.035 (3)	0.038 (3)	−0.005 (2)	0.014 (3)	−0.004 (2)
C6	0.033 (3)	0.034 (3)	0.036 (3)	0.003 (2)	0.015 (2)	0.011 (2)
C8	0.044 (4)	0.061 (4)	0.043 (3)	−0.012 (3)	−0.004 (3)	0.007 (3)
C1	0.060 (4)	0.036 (3)	0.032 (3)	−0.005 (2)	0.020 (3)	−0.002 (2)
C3	0.045 (3)	0.052 (3)	0.031 (3)	−0.009 (3)	0.002 (2)	0.004 (2)
C4	0.035 (3)	0.050 (3)	0.046 (3)	−0.001 (2)	0.007 (3)	0.001 (2)
N2	0.045 (3)	0.070 (4)	0.069 (4)	−0.009 (3)	0.017 (3)	0.004 (3)
C7	0.039 (3)	0.051 (4)	0.055 (4)	0.000 (2)	0.008 (3)	0.013 (3)

Br1—C10	1.904 (5)	C9—H9A	0.9300
C10—C9	1.365 (8)	C6—C7	1.371 (7)
C10—C5	1.397 (6)	C8—C7	1.379 (9)
N1—C6	1.355 (6)	C8—H8A	0.9300
N1—C1	1.353 (8)	C1—H1B	0.9300
N1—H1A	0.8600	C3—C4	1.454 (7)
C5—C2	1.420 (7)	C3—H3A	0.9700
C5—C6	1.425 (6)	C3—H3B	0.9700
C2—C1	1.374 (7)	C4—N2	1.121 (7)
C2—C3	1.509 (7)	C7—H7A	0.9300
C9—C8	1.389 (9)
C9—C10—C5	120.5 (5)	C7—C6—C5	123.7 (5)
C9—C10—Br1	118.5 (4)	C7—C8—C9	120.1 (6)
C5—C10—Br1	121.0 (4)	C7—C8—H8A	119.9
C6—N1—C1	110.0 (4)	C9—C8—H8A	119.9
C6—N1—H1A	125.0	C2—C1—N1	110.1 (5)
C1—N1—H1A	125.0	C2—C1—H1B	125.0
C10—C5—C2	136.8 (5)	N1—C1—H1B	125.0
C10—C5—C6	116.0 (5)	C4—C3—C2	112.6 (4)
C2—C5—C6	107.1 (4)	C4—C3—H3A	109.1
C1—C2—C5	106.0 (4)	C2—C3—H3A	109.1
C1—C2—C3	124.3 (5)	C4—C3—H3B	109.1
C5—C2—C3	129.7 (4)	C2—C3—H3B	109.1
C10—C9—C8	121.8 (5)	H3A—C3—H3B	107.8
C10—C9—H9A	119.1	N2—C4—C3	178.9 (6)
C8—C9—H9A	119.1	C6—C7—C8	117.8 (5)
N1—C6—C7	129.5 (5)	C6—C7—H7A	121.1
N1—C6—C5	106.8 (5)	C8—C7—H7A	121.1

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86	2.45	3.218 (7)	148.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.86	2.45	3.218 (7)	148

Symmetry code: (i) .