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

Li, J.-F.; Luo, Y.-H.

doi:10.1107/S1600536811053372

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o144

doi:10.1107/S1600536811053372

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

Jin-Feng Li ^a ^* and Yang-Hui Luo ^a

^aKey Laboratory of Urban and Architectural Heritage Conservation, (Southeast University), Ministry of Education, Nanjing 210096, People's Republic of China, and, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 5 December 2011; accepted 12 December 2011; online 17 December 2011)

In the title compound, C₁₀H₇ClN₂, the carbonitrile group is twisted away from the plane of the indole ring system [C_cy—C_me—C_ar—C_ar = −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 π–π stacking interactions [minimum centroid–centroid separation = 3.663 (3) Å] are also observed.

Related literature

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

Experimental

Crystal data

C₁₀H₇ClN₂
M_r = 190.63
Monoclinic, P 2₁ /c
a = 9.761 (2) Å
b = 11.205 (2) Å
c = 8.7791 (18) Å
β = 100.39 (3)°
V = 944.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 K
0.20 × 0.12 × 0.10 mm

Data collection

Rigaku SCXmini CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.950, T_max = 0.965
8938 measured reflections
2122 independent reflections
1247 reflections with I > 2σ(I)
R_int = 0.134

Refinement

R[F² > 2σ(F²)] = 0.110
wR(F²) = 0.312
S = 1.05
2122 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H4A⋯N1ⁱ	0.86	2.23	3.016 (6)	151
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811053372/hb6557sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053372/hb6557Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053372/hb6557Isup3.cml

checkCIF report

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.

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

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	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

C₁₀H₇ClN₂	F(000) = 392
M_r = 190.63	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2122 reflections
a = 9.761 (2) Å	θ = 3.0–27.5°
b = 11.205 (2) Å	µ = 0.35 mm⁻¹
c = 8.7791 (18) Å	T = 293 K
β = 100.39 (3)°	Prism, colourless
V = 944.4 (3) Å³	0.20 × 0.12 × 0.10 mm
Z = 4

Data collection top

Rigaku SCXmini CCD diffractometer	2122 independent reflections
Radiation source: fine-focus sealed tube	1247 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.134
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD_Profile_fitting scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→13
T_min = 0.950, T_max = 0.965	l = −11→11
8938 measured reflections

Refinement top

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)] = 0.110	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.312	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1465P)² + 0.5597P] where P = (F_o² + 2F_c²)/3
2122 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₀H₇ClN₂	V = 944.4 (3) Å³
M_r = 190.63	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.761 (2) Å	µ = 0.35 mm⁻¹
b = 11.205 (2) Å	T = 293 K
c = 8.7791 (18) Å	0.20 × 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)
T_min = 0.950, T_max = 0.965	R_int = 0.134
8938 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.110	0 restraints
wR(F²) = 0.312	H-atom parameters constrained
S = 1.05	Δρ_max = 0.51 e Å⁻³
2122 reflections	Δρ_min = −0.46 e Å⁻³
118 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 > 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

	x	y	z	U_iso*/U_eq
Cl1	0.24329 (14)	0.04179 (19)	0.32068 (19)	0.0959 (8)
N1	1.0357 (5)	0.3256 (5)	0.0579 (6)	0.0929 (16)
N2	0.7608 (4)	−0.0082 (4)	0.2478 (4)	0.0578 (10)
H4A	0.7910	−0.0635	0.3133	0.069*
C11	0.9347 (5)	0.2792 (4)	0.0093 (5)	0.0628 (12)
C12	0.8029 (6)	0.2208 (6)	−0.0508 (6)	0.0842 (18)
H12A	0.8115	0.1777	−0.1445	0.101*
H12B	0.7314	0.2810	−0.0781	0.101*
C13	0.7581 (4)	0.1343 (4)	0.0646 (5)	0.0578 (12)
C14	0.8382 (5)	0.0517 (5)	0.1549 (6)	0.0673 (14)
H14A	0.9319	0.0378	0.1539	0.081*
C15	0.6203 (4)	0.1262 (4)	0.1028 (4)	0.0481 (10)
C16	0.6263 (4)	0.0360 (3)	0.2172 (5)	0.0467 (10)
C17	0.5117 (4)	0.0061 (4)	0.2868 (5)	0.0519 (11)
H17A	0.5167	−0.0525	0.3627	0.062*
C18	0.3907 (5)	0.0705 (4)	0.2342 (5)	0.0588 (12)
C19	0.3788 (5)	0.1573 (4)	0.1185 (6)	0.0646 (13)
H19A	0.2943	0.1961	0.0862	0.078*
C20	0.4923 (5)	0.1854 (4)	0.0522 (5)	0.0568 (11)
H20A	0.4848	0.2430	−0.0252	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0512 (9)	0.1570 (18)	0.0826 (11)	−0.0064 (8)	0.0201 (7)	−0.0179 (9)
N1	0.070 (3)	0.108 (4)	0.096 (4)	−0.037 (3)	0.003 (2)	0.003 (3)
N2	0.042 (2)	0.073 (2)	0.054 (2)	0.0056 (18)	−0.0036 (15)	0.0129 (18)
C11	0.056 (3)	0.067 (3)	0.067 (3)	−0.009 (2)	0.013 (2)	0.001 (2)
C12	0.078 (3)	0.111 (4)	0.056 (3)	−0.046 (3)	−0.006 (2)	0.014 (3)
C13	0.050 (2)	0.074 (3)	0.044 (2)	−0.018 (2)	−0.0083 (17)	0.0047 (19)
C14	0.038 (2)	0.097 (4)	0.064 (3)	−0.003 (2)	0.001 (2)	0.005 (2)
C15	0.046 (2)	0.051 (2)	0.042 (2)	−0.0085 (18)	−0.0082 (16)	−0.0029 (16)
C16	0.041 (2)	0.049 (2)	0.046 (2)	−0.0003 (17)	−0.0047 (16)	−0.0014 (16)
C17	0.054 (3)	0.054 (2)	0.046 (2)	−0.003 (2)	0.0033 (19)	0.0004 (18)
C18	0.047 (2)	0.067 (3)	0.061 (3)	−0.001 (2)	0.0034 (19)	−0.013 (2)
C19	0.053 (3)	0.066 (3)	0.068 (3)	0.013 (2)	−0.008 (2)	−0.012 (2)
C20	0.062 (3)	0.047 (2)	0.053 (2)	0.003 (2)	−0.0123 (19)	0.0017 (17)

Geometric parameters (Å, º) top

Cl1—C18	1.773 (5)	C14—H14A	0.9300
N1—C11	1.128 (6)	C15—C20	1.413 (6)
N2—C14	1.381 (6)	C15—C16	1.419 (6)
N2—C16	1.384 (5)	C16—C17	1.408 (6)
N2—H4A	0.8600	C17—C18	1.390 (6)
C11—C12	1.455 (7)	C17—H17A	0.9300
C12—C13	1.522 (6)	C18—C19	1.396 (7)
C12—H12A	0.9700	C19—C20	1.379 (7)
C12—H12B	0.9700	C19—H19A	0.9300
C13—C14	1.368 (7)	C20—H20A	0.9300
C13—C15	1.447 (6)

C14—N2—C16	108.2 (4)	C20—C15—C13	134.7 (4)
C14—N2—H4A	125.9	C16—C15—C13	106.7 (4)
C16—N2—H4A	125.9	N2—C16—C17	129.1 (4)
N1—C11—C12	178.7 (6)	N2—C16—C15	108.0 (4)
C11—C12—C13	112.7 (4)	C17—C16—C15	122.8 (4)
C11—C12—H12A	109.0	C18—C17—C16	115.2 (4)
C13—C12—H12A	109.0	C18—C17—H17A	122.4
C11—C12—H12B	109.0	C16—C17—H17A	122.4
C13—C12—H12B	109.0	C17—C18—C19	123.9 (4)
H12A—C12—H12B	107.8	C17—C18—Cl1	118.0 (4)
C14—C13—C15	106.3 (4)	C19—C18—Cl1	118.0 (4)
C14—C13—C12	127.8 (5)	C20—C19—C18	119.9 (4)
C15—C13—C12	125.8 (4)	C20—C19—H19A	120.0
C13—C14—N2	110.8 (4)	C18—C19—H19A	120.0
C13—C14—H14A	124.6	C19—C20—C15	119.5 (4)
N2—C14—H14A	124.6	C19—C20—H20A	120.3
C20—C15—C16	118.6 (4)	C15—C20—H20A	120.3

N1—C11—C12—C13	−68 (28)	C13—C15—C16—N2	0.3 (4)
C11—C12—C13—C14	−44.7 (8)	C20—C15—C16—C17	−2.5 (6)
C11—C12—C13—C15	133.6 (5)	C13—C15—C16—C17	177.6 (4)
C15—C13—C14—N2	0.0 (6)	N2—C16—C17—C18	177.5 (4)
C12—C13—C14—N2	178.6 (4)	C15—C16—C17—C18	0.8 (6)
C16—N2—C14—C13	0.2 (6)	C16—C17—C18—C19	1.3 (6)
C14—C13—C15—C20	−180.0 (5)	C16—C17—C18—Cl1	−177.9 (3)
C12—C13—C15—C20	1.4 (8)	C17—C18—C19—C20	−1.6 (7)
C14—C13—C15—C16	−0.1 (5)	Cl1—C18—C19—C20	177.6 (4)
C12—C13—C15—C16	−178.8 (4)	C18—C19—C20—C15	−0.3 (7)
C14—N2—C16—C17	−177.4 (4)	C16—C15—C20—C19	2.2 (6)
C14—N2—C16—C15	−0.3 (5)	C13—C15—C20—C19	−178.0 (5)
C20—C15—C16—N2	−179.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H4A···N1ⁱ	0.86	2.23	3.016 (6)	151

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₇ClN₂
M_r	190.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.761 (2), 11.205 (2), 8.7791 (18)
β (°)	100.39 (3)
V (Å³)	944.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.20 × 0.12 × 0.10

Data collection
Diffractometer	Rigaku SCXmini CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.950, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	8938, 2122, 1247
R_int	0.134
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.110, 0.312, 1.05
No. of reflections	2122
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.46

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H4A···N1ⁱ	0.86	2.23	3.016 (6)	151

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Acknowledgements

We thank Southeast University for support.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Ge, Y.-H., Pan, M.-L., Xu, J. & Luo, Y.-H. (2012). Acta Cryst. E68, o141. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar