supplementary materials


hb6557 scheme

Acta Cryst. (2012). E68, o144    [ doi:10.1107/S1600536811053372 ]

2-(6-Chloro-1H-indol-3-yl)acetonitrile

J.-F. Li and Y.-H. Luo

Abstract top

In the title compound, C10H7ClN2, the carbonitrile group is twisted away from the plane of the indole ring system [Ccy-Cme-Car-Car = -44.7 (8)°; cy = cyanide, me = methylene and ar = aromatic]. In the crystal, N-H...N hydrogen bonds link the molecules into C(7) chains propagating in [010]. Aromatic [pi]-[pi] stacking interactions [minimum centroid-centroid separation = 3.663 (3) Å] are also observed.

Related literature top

For a related structure, see: Ge et al. (2012).

Experimental top

The title compound was obtained commercially from ChemFuture PharmaTech, Ltd (Nanjing, Jiangsu). and were used as received without further purification. Colourless prisms were obtained by slow evaporation of a methanol solution.

Refinement top

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 (CH2) and N—H = 0.86 Å with Uiso(H) =1.2Ueq.

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: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing view down the a axis showing hydrogen bonds as dashed lines.
2-(6-Chloro-1H-indol-3-yl)acetonitrile top
Crystal data top
C10H7ClN2F(000) = 392
Mr = 190.63Dx = 1.341 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2122 reflections
a = 9.761 (2) Åθ = 3.0–27.5°
b = 11.205 (2) ŵ = 0.35 mm1
c = 8.7791 (18) ÅT = 293 K
β = 100.39 (3)°Prism, colourless
V = 944.4 (3) Å30.20 × 0.12 × 0.10 mm
Z = 4
Data collection top
Rigaku SCXmini CCD
diffractometer
2122 independent reflections
Radiation source: fine-focus sealed tube1247 reflections with I > 2σ(I)
graphiteRint = 0.134
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scansh = 1212
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1413
Tmin = 0.950, Tmax = 0.965l = 1111
8938 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)] = 0.110Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.312H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1465P)2 + 0.5597P]
where P = (Fo2 + 2Fc2)/3
2122 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.46 e Å3
Crystal data top
C10H7ClN2V = 944.4 (3) Å3
Mr = 190.63Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.761 (2) ŵ = 0.35 mm1
b = 11.205 (2) ÅT = 293 K
c = 8.7791 (18) Å0.20 × 0.12 × 0.10 mm
β = 100.39 (3)°
Data collection top
Rigaku SCXmini CCD
diffractometer
2122 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1247 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.965Rint = 0.134
8938 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.110H-atom parameters constrained
wR(F2) = 0.312Δρmax = 0.51 e Å3
S = 1.05Δρmin = 0.46 e Å3
2122 reflectionsAbsolute structure: ?
118 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Cl10.24329 (14)0.04179 (19)0.32068 (19)0.0959 (8)
N11.0357 (5)0.3256 (5)0.0579 (6)0.0929 (16)
N20.7608 (4)0.0082 (4)0.2478 (4)0.0578 (10)
H4A0.79100.06350.31330.069*
C110.9347 (5)0.2792 (4)0.0093 (5)0.0628 (12)
C120.8029 (6)0.2208 (6)0.0508 (6)0.0842 (18)
H12A0.81150.17770.14450.101*
H12B0.73140.28100.07810.101*
C130.7581 (4)0.1343 (4)0.0646 (5)0.0578 (12)
C140.8382 (5)0.0517 (5)0.1549 (6)0.0673 (14)
H14A0.93190.03780.15390.081*
C150.6203 (4)0.1262 (4)0.1028 (4)0.0481 (10)
C160.6263 (4)0.0360 (3)0.2172 (5)0.0467 (10)
C170.5117 (4)0.0061 (4)0.2868 (5)0.0519 (11)
H17A0.51670.05250.36270.062*
C180.3907 (5)0.0705 (4)0.2342 (5)0.0588 (12)
C190.3788 (5)0.1573 (4)0.1185 (6)0.0646 (13)
H19A0.29430.19610.08620.078*
C200.4923 (5)0.1854 (4)0.0522 (5)0.0568 (11)
H20A0.48480.24300.02520.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0512 (9)0.1570 (18)0.0826 (11)0.0064 (8)0.0201 (7)0.0179 (9)
N10.070 (3)0.108 (4)0.096 (4)0.037 (3)0.003 (2)0.003 (3)
N20.042 (2)0.073 (2)0.054 (2)0.0056 (18)0.0036 (15)0.0129 (18)
C110.056 (3)0.067 (3)0.067 (3)0.009 (2)0.013 (2)0.001 (2)
C120.078 (3)0.111 (4)0.056 (3)0.046 (3)0.006 (2)0.014 (3)
C130.050 (2)0.074 (3)0.044 (2)0.018 (2)0.0083 (17)0.0047 (19)
C140.038 (2)0.097 (4)0.064 (3)0.003 (2)0.001 (2)0.005 (2)
C150.046 (2)0.051 (2)0.042 (2)0.0085 (18)0.0082 (16)0.0029 (16)
C160.041 (2)0.049 (2)0.046 (2)0.0003 (17)0.0047 (16)0.0014 (16)
C170.054 (3)0.054 (2)0.046 (2)0.003 (2)0.0033 (19)0.0004 (18)
C180.047 (2)0.067 (3)0.061 (3)0.001 (2)0.0034 (19)0.013 (2)
C190.053 (3)0.066 (3)0.068 (3)0.013 (2)0.008 (2)0.012 (2)
C200.062 (3)0.047 (2)0.053 (2)0.003 (2)0.0123 (19)0.0017 (17)
Geometric parameters (Å, °) top
Cl1—C181.773 (5)C14—H14A0.9300
N1—C111.128 (6)C15—C201.413 (6)
N2—C141.381 (6)C15—C161.419 (6)
N2—C161.384 (5)C16—C171.408 (6)
N2—H4A0.8600C17—C181.390 (6)
C11—C121.455 (7)C17—H17A0.9300
C12—C131.522 (6)C18—C191.396 (7)
C12—H12A0.9700C19—C201.379 (7)
C12—H12B0.9700C19—H19A0.9300
C13—C141.368 (7)C20—H20A0.9300
C13—C151.447 (6)
C14—N2—C16108.2 (4)C20—C15—C13134.7 (4)
C14—N2—H4A125.9C16—C15—C13106.7 (4)
C16—N2—H4A125.9N2—C16—C17129.1 (4)
N1—C11—C12178.7 (6)N2—C16—C15108.0 (4)
C11—C12—C13112.7 (4)C17—C16—C15122.8 (4)
C11—C12—H12A109.0C18—C17—C16115.2 (4)
C13—C12—H12A109.0C18—C17—H17A122.4
C11—C12—H12B109.0C16—C17—H17A122.4
C13—C12—H12B109.0C17—C18—C19123.9 (4)
H12A—C12—H12B107.8C17—C18—Cl1118.0 (4)
C14—C13—C15106.3 (4)C19—C18—Cl1118.0 (4)
C14—C13—C12127.8 (5)C20—C19—C18119.9 (4)
C15—C13—C12125.8 (4)C20—C19—H19A120.0
C13—C14—N2110.8 (4)C18—C19—H19A120.0
C13—C14—H14A124.6C19—C20—C15119.5 (4)
N2—C14—H14A124.6C19—C20—H20A120.3
C20—C15—C16118.6 (4)C15—C20—H20A120.3
N1—C11—C12—C1368 (28)C13—C15—C16—N20.3 (4)
C11—C12—C13—C1444.7 (8)C20—C15—C16—C172.5 (6)
C11—C12—C13—C15133.6 (5)C13—C15—C16—C17177.6 (4)
C15—C13—C14—N20.0 (6)N2—C16—C17—C18177.5 (4)
C12—C13—C14—N2178.6 (4)C15—C16—C17—C180.8 (6)
C16—N2—C14—C130.2 (6)C16—C17—C18—C191.3 (6)
C14—C13—C15—C20180.0 (5)C16—C17—C18—Cl1177.9 (3)
C12—C13—C15—C201.4 (8)C17—C18—C19—C201.6 (7)
C14—C13—C15—C160.1 (5)Cl1—C18—C19—C20177.6 (4)
C12—C13—C15—C16178.8 (4)C18—C19—C20—C150.3 (7)
C14—N2—C16—C17177.4 (4)C16—C15—C20—C192.2 (6)
C14—N2—C16—C150.3 (5)C13—C15—C20—C19178.0 (5)
C20—C15—C16—N2179.8 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H4A···N1i0.862.233.016 (6)151
Symmetry codes: (i) −x+2, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
N2—H4A···N1i0.862.233.016 (6)151
Symmetry codes: (i) −x+2, y−1/2, −z+1/2.
Acknowledgements top

We thank Southeast University for support.

references
References top

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Ge, Y.-H., Pan, M.-L., Xu, J. & Luo, Y.-H. (2012). Acta Cryst. E68, o141.

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

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