2-(7-Methyl-1H-indol-3-yl)acetonitrile

Ge, Y.-H.; Pan, M.-L.; Xu, J.; Luo, Y.-H.

doi:10.1107/S1600536811053396

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o141

doi:10.1107/S1600536811053396

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2-(7-Methyl-1H-indol-3-yl)acetonitrile

Yu-Hua Ge,^a ^* Mei-Ling Pan,^a Jian Xu ^a and Yang-Hui Luo ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: peluoyh@sina.com

(Received 1 December 2011; accepted 12 December 2011; online 17 December 2011)

In the title compound, C₁₁H₁₀N₂, the carbonitrile group is twisted away from the indole plane [C_cy—C_me—C_ar—C_ar = 66.6 (2)°; cy = cyanide, me = methylene and ar = aromatic]. In the crystal, N—H⋯N hydrogen bonds link the molecules into C(7) chains propagating in the [001] direction.

Related literature

For background to indole derivatives as pharmaceuticals, see: Kunzer & Wendt (2011 ).

Experimental

Crystal data

C₁₁H₁₀N₂
M_r = 170.21
Monoclinic, P 2₁ /c
a = 6.9962 (14) Å
b = 8.9445 (18) Å
c = 15.406 (3) Å
β = 97.97 (3)°
V = 954.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.26 × 0.24 × 0.15 mm

Data collection

Rigaku SCXmini CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.981, T_max = 0.989
9402 measured reflections
2160 independent reflections
1418 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.154
S = 1.05
2160 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2ⁱ	0.86	2.24	3.022 (2)	151
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536811053396/hb6546sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053396/hb6546Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053396/hb6546Isup3.cml

checkCIF report

Related literature top

For background to indole derivatives as pharmaceuticals, see: Kunzer & Wendt (2011).

Experimental top

Colourless blocks of (I) were obstained by slow evaporation of a methanol solution of a commercially supplied sample.

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 with hydrogen bonds shown as dashed lines.

2-(7-Methyl-1H-indol-3-yl)acetonitrile top

Crystal data top

C₁₁H₁₀N₂	F(000) = 360
M_r = 170.21	D_x = 1.184 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2175 reflections
a = 6.9962 (14) Å	θ = 2.7–27.5°
b = 8.9445 (18) Å	µ = 0.07 mm⁻¹
c = 15.406 (3) Å	T = 293 K
β = 97.97 (3)°	Block, colourless
V = 954.7 (3) Å³	0.26 × 0.24 × 0.15 mm
Z = 4

Data collection top

Rigaku SCXmini CCD diffractometer	2160 independent reflections
Radiation source: fine-focus sealed tube	1418 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ω scans	θ_max = 27.5°, θ_min = 3.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −9→9
T_min = 0.981, T_max = 0.989	k = −11→11
9402 measured reflections	l = −19→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0708P)² + 0.0707P] where P = (F_o² + 2F_c²)/3
2160 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₁H₁₀N₂	V = 954.7 (3) Å³
M_r = 170.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.9962 (14) Å	µ = 0.07 mm⁻¹
b = 8.9445 (18) Å	T = 293 K
c = 15.406 (3) Å	0.26 × 0.24 × 0.15 mm
β = 97.97 (3)°

Data collection top

Rigaku SCXmini CCD diffractometer	2160 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1418 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.989	R_int = 0.058
9402 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
2160 reflections	Δρ_min = −0.17 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
C1	−0.0179 (3)	0.6121 (2)	0.21424 (12)	0.0587 (5)
H1B	−0.1278	0.6642	0.1903	0.070*
C2	0.0270 (2)	0.57655 (18)	0.30000 (11)	0.0511 (4)
C3	0.2072 (2)	0.49843 (17)	0.30912 (10)	0.0473 (4)
C4	0.3276 (3)	0.43296 (19)	0.37953 (12)	0.0613 (5)
H4A	0.2955	0.4369	0.4361	0.074*
C5	0.4936 (3)	0.3631 (2)	0.36311 (16)	0.0758 (6)
H5A	0.5736	0.3187	0.4092	0.091*
C6	0.5451 (3)	0.3571 (2)	0.27861 (17)	0.0768 (6)
H6A	0.6588	0.3088	0.2703	0.092*
C7	0.4334 (3)	0.4204 (2)	0.20730 (13)	0.0644 (5)
C8	0.2629 (2)	0.48979 (17)	0.22467 (10)	0.0506 (4)
C9	0.4896 (4)	0.4170 (3)	0.11583 (16)	0.0958 (8)
H9A	0.6091	0.3639	0.1168	0.144*
H9B	0.5047	0.5175	0.0959	0.144*
H9C	0.3905	0.3676	0.0768	0.144*
C10	−0.0948 (3)	0.6089 (2)	0.37116 (13)	0.0678 (5)
H10A	−0.2171	0.6509	0.3449	0.081*
H10B	−0.1216	0.5158	0.3994	0.081*
C11	−0.0021 (3)	0.7128 (2)	0.43771 (12)	0.0621 (5)
N1	0.1212 (2)	0.56067 (16)	0.16799 (9)	0.0600 (4)
H1A	0.1207	0.5707	0.1124	0.072*
N2	0.0698 (3)	0.7913 (2)	0.48993 (11)	0.0856 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0586 (10)	0.0557 (10)	0.0580 (11)	0.0065 (8)	−0.0048 (9)	−0.0008 (8)
C2	0.0529 (9)	0.0500 (9)	0.0495 (10)	0.0010 (7)	0.0040 (7)	−0.0038 (7)
C3	0.0537 (9)	0.0413 (8)	0.0454 (9)	−0.0049 (7)	0.0021 (7)	0.0014 (6)
C4	0.0659 (11)	0.0584 (11)	0.0562 (10)	−0.0058 (9)	−0.0030 (9)	0.0094 (8)
C5	0.0656 (12)	0.0597 (12)	0.0951 (16)	0.0036 (10)	−0.0131 (11)	0.0164 (11)
C6	0.0601 (12)	0.0574 (12)	0.1126 (18)	0.0064 (9)	0.0108 (12)	−0.0067 (12)
C7	0.0642 (11)	0.0542 (11)	0.0780 (13)	−0.0045 (9)	0.0207 (10)	−0.0131 (9)
C8	0.0585 (10)	0.0425 (9)	0.0503 (9)	−0.0045 (7)	0.0055 (8)	−0.0040 (7)
C9	0.0977 (17)	0.0985 (17)	0.1011 (18)	−0.0132 (14)	0.0481 (14)	−0.0277 (13)
C10	0.0606 (11)	0.0731 (12)	0.0715 (12)	−0.0027 (9)	0.0156 (10)	−0.0097 (10)
C11	0.0675 (11)	0.0716 (12)	0.0490 (10)	0.0085 (10)	0.0150 (9)	0.0013 (9)
N1	0.0748 (10)	0.0628 (9)	0.0404 (8)	−0.0020 (8)	0.0012 (7)	0.0008 (6)
N2	0.1026 (14)	0.0986 (14)	0.0549 (10)	0.0050 (11)	0.0087 (9)	−0.0152 (9)

Geometric parameters (Å, º) top

C1—C2	1.353 (2)	C6—H6A	0.9300
C1—N1	1.364 (2)	C7—C8	1.403 (2)
C1—H1B	0.9300	C7—C9	1.515 (3)
C2—C3	1.431 (2)	C8—N1	1.381 (2)
C2—C10	1.507 (2)	C9—H9A	0.9600
C3—C4	1.405 (2)	C9—H9B	0.9600
C3—C8	1.411 (2)	C9—H9C	0.9600
C4—C5	1.373 (3)	C10—C11	1.467 (3)
C4—H4A	0.9300	C10—H10A	0.9700
C5—C6	1.399 (3)	C10—H10B	0.9700
C5—H5A	0.9300	C11—N2	1.131 (2)
C6—C7	1.378 (3)	N1—H1A	0.8600

C2—C1—N1	110.17 (15)	C8—C7—C9	121.5 (2)
C2—C1—H1B	124.9	N1—C8—C7	129.60 (17)
N1—C1—H1B	124.9	N1—C8—C3	106.97 (15)
C1—C2—C3	107.04 (15)	C7—C8—C3	123.43 (17)
C1—C2—C10	125.94 (16)	C7—C9—H9A	109.5
C3—C2—C10	126.99 (15)	C7—C9—H9B	109.5
C4—C3—C8	118.43 (16)	H9A—C9—H9B	109.5
C4—C3—C2	134.80 (16)	C7—C9—H9C	109.5
C8—C3—C2	106.76 (14)	H9A—C9—H9C	109.5
C5—C4—C3	118.63 (18)	H9B—C9—H9C	109.5
C5—C4—H4A	120.7	C11—C10—C2	112.97 (15)
C3—C4—H4A	120.7	C11—C10—H10A	109.0
C4—C5—C6	121.50 (19)	C2—C10—H10A	109.0
C4—C5—H5A	119.2	C11—C10—H10B	109.0
C6—C5—H5A	119.2	C2—C10—H10B	109.0
C7—C6—C5	122.37 (19)	H10A—C10—H10B	107.8
C7—C6—H6A	118.8	N2—C11—C10	179.0 (2)
C5—C6—H6A	118.8	C1—N1—C8	109.06 (14)
C6—C7—C8	115.63 (18)	C1—N1—H1A	125.5
C6—C7—C9	122.82 (19)	C8—N1—H1A	125.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.86	2.24	3.022 (2)	151

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₂
M_r	170.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.9962 (14), 8.9445 (18), 15.406 (3)
β (°)	97.97 (3)
V (Å³)	954.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.26 × 0.24 × 0.15

Data collection
Diffractometer	Rigaku SCXmini CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.981, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	9402, 2160, 1418
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.154, 1.05
No. of reflections	2160
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

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
N1—H1A···N2ⁱ	0.86	2.24	3.022 (2)	151

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

We thank Southeast University for support.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Kunzer, A. R. & Wendt, M. D. (2011). Tetrahedron, 52, 1815–1818. CrossRef CAS 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