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

Lu, Y.-H.; Pan, M.-L.; Luo, Y.-H.

doi:10.1107/S1600536811053360

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o143

doi:10.1107/S1600536811053360

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

Yong-Hong Lu,^a ^* Mei-Ling Pan ^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: chmsunbw@seu.edu.cn

(Received 2 December 2011; accepted 12 December 2011; online 17 December 2011)

In the title compound, C₁₁H₁₀N₂O, the cyanide group is twisted away from the indole-ring plane [C_cy—C_me—C_ar—C_ar = 70.7 (2)°; cy = cyanide, me = methylene, ar = aromatic], whereas the methoxy C atom is almost coplanar with the ring system [displacement = 0.014 (5) Å]. In the crystal, N—H⋯N hydrogen bonds link the molecules into C(7) chains propagating in [100].

Related literature

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

Experimental

Crystal data

C₁₁H₁₀N₂O
M_r = 186.21
Monoclinic, P 2₁ /c
a = 8.3182 (17) Å
b = 13.062 (3) Å
c = 9.3867 (19) Å
β = 101.53 (3)°
V = 999.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 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 = 0.979, T_max = 0.988
9998 measured reflections
2283 independent reflections
1235 reflections with I > 2σ(I)
R_int = 0.109

Refinement

R[F² > 2σ(F²)] = 0.088
wR(F²) = 0.298
S = 1.07
2283 reflections
127 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.45 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	2.19	3.028 (4)	164
Symmetry code: (i) x+1, y, z.

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/S1600536811053360/hb6547sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053360/hb6547Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053360/hb6547Isup3.cml

checkCIF report

Related literature top

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

Experimental top

Colourless blocks of the title compound, obtained from a commercial source, 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-(4-Methoxy-1H-indol-3-yl)acetonitrile top

Crystal data top

C₁₁H₁₀N₂O	F(000) = 392
M_r = 186.21	D_x = 1.238 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2283 reflections
a = 8.3182 (17) Å	θ = 3.1–27.5°
b = 13.062 (3) Å	µ = 0.08 mm⁻¹
c = 9.3867 (19) Å	T = 293 K
β = 101.53 (3)°	Block, colourless
V = 999.3 (3) Å³	0.26 × 0.24 × 0.15 mm
Z = 4

Data collection top

Rigaku SCXmini CCD diffractometer	2283 independent reflections
Radiation source: fine-focus sealed tube	1235 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.109
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
CCD_Profile_fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
T_min = 0.979, T_max = 0.988	l = −12→12
9998 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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.298	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1429P)² + 0.1759P] where P = (F_o² + 2F_c²)/3
2283 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.38 e Å⁻³
12 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₁H₁₀N₂O	V = 999.3 (3) Å³
M_r = 186.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3182 (17) Å	µ = 0.08 mm⁻¹
b = 13.062 (3) Å	T = 293 K
c = 9.3867 (19) Å	0.26 × 0.24 × 0.15 mm
β = 101.53 (3)°

Data collection top

Rigaku SCXmini CCD diffractometer	2283 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1235 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.988	R_int = 0.109
9998 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	12 restraints
wR(F²) = 0.298	H-atom parameters constrained
S = 1.07	Δρ_max = 0.38 e Å⁻³
2283 reflections	Δρ_min = −0.45 e Å⁻³
127 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
C5	0.4959 (3)	0.6202 (2)	0.1157 (3)	0.0567 (7)
C2	0.4374 (4)	0.6934 (2)	0.0033 (3)	0.0610 (8)
C10	0.4215 (5)	0.5425 (2)	0.1837 (3)	0.0724 (9)
O1	0.2566 (3)	0.53144 (18)	0.1335 (3)	0.0941 (9)
N1	0.7052 (4)	0.7163 (3)	0.0794 (4)	0.0927 (11)
H1A	0.8020	0.7415	0.0864	0.111*
C6	0.6656 (4)	0.6374 (3)	0.1600 (4)	0.0770 (10)
N2	0.0524 (4)	0.7726 (3)	0.0570 (4)	0.0978 (11)
C4	0.1475 (4)	0.7424 (3)	−0.0049 (4)	0.0760 (10)
C1	0.5681 (5)	0.7495 (3)	−0.0147 (4)	0.0811 (10)
H1B	0.5653	0.8027	−0.0810	0.097*
C3	0.2684 (4)	0.7039 (3)	−0.0858 (3)	0.0806 (10)
H3A	0.2720	0.7501	−0.1661	0.097*
H3B	0.2323	0.6376	−0.1266	0.097*
C9	0.5176 (6)	0.4845 (3)	0.2916 (5)	0.1116 (12)
H9A	0.4708	0.4329	0.3382	0.134*
C7	0.7644 (6)	0.5791 (3)	0.2705 (4)	0.1120 (12)
H7A	0.8762	0.5912	0.3007	0.134*
C8	0.6861 (6)	0.5044 (4)	0.3297 (5)	0.1123 (11)
H8A	0.7486	0.4634	0.4008	0.135*
C11	0.1740 (7)	0.4533 (4)	0.1992 (6)	0.141 (2)
H11A	0.0594	0.4535	0.1553	0.212*
H11B	0.1872	0.4664	0.3015	0.212*
H11C	0.2203	0.3877	0.1846	0.212*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C5	0.0627 (17)	0.0571 (15)	0.0523 (15)	−0.0009 (12)	0.0163 (12)	−0.0114 (12)
C2	0.0707 (18)	0.0654 (17)	0.0507 (15)	−0.0105 (13)	0.0213 (13)	−0.0056 (13)
C10	0.099 (2)	0.0579 (17)	0.0641 (19)	0.0040 (16)	0.0265 (18)	−0.0044 (13)
O1	0.107 (2)	0.0782 (16)	0.1058 (19)	−0.0287 (13)	0.0425 (16)	0.0047 (13)
N1	0.0673 (18)	0.104 (2)	0.116 (3)	−0.0194 (16)	0.0396 (18)	−0.041 (2)
C6	0.074 (2)	0.082 (2)	0.077 (2)	0.0092 (17)	0.0204 (17)	−0.0287 (18)
N2	0.0590 (17)	0.125 (3)	0.104 (3)	−0.0091 (17)	0.0054 (17)	−0.009 (2)
C4	0.0611 (19)	0.089 (2)	0.071 (2)	−0.0100 (17)	−0.0037 (16)	0.0014 (17)
C1	0.097 (3)	0.077 (2)	0.082 (2)	−0.0183 (18)	0.048 (2)	−0.0083 (17)
C3	0.086 (2)	0.098 (2)	0.0561 (18)	−0.0022 (18)	0.0085 (16)	0.0000 (16)
C9	0.146 (2)	0.0971 (19)	0.0851 (18)	0.054 (2)	0.0086 (18)	−0.0107 (15)
C7	0.140 (3)	0.102 (2)	0.0871 (18)	0.058 (2)	0.0063 (18)	−0.0196 (15)
C8	0.145 (2)	0.0994 (19)	0.0859 (17)	0.059 (2)	0.0063 (17)	−0.0142 (14)
C11	0.195 (5)	0.090 (3)	0.167 (5)	−0.063 (3)	0.105 (4)	−0.013 (3)

Geometric parameters (Å, º) top

C5—C6	1.407 (4)	C4—C3	1.465 (6)
C5—C10	1.407 (4)	C1—H1B	0.9300
C5—C2	1.435 (4)	C3—H3A	0.9700
C2—C1	1.350 (4)	C3—H3B	0.9700
C2—C3	1.492 (4)	C9—C8	1.400 (7)
C10—O1	1.365 (4)	C9—H9A	0.9300
C10—C9	1.384 (5)	C7—C8	1.353 (7)
O1—C11	1.437 (4)	C7—H7A	0.9300
N1—C6	1.357 (5)	C8—H8A	0.9300
N1—C1	1.366 (5)	C11—H11A	0.9600
N1—H1A	0.8600	C11—H11B	0.9600
C6—C7	1.411 (5)	C11—H11C	0.9600
N2—C4	1.142 (5)

C6—C5—C10	119.2 (3)	C4—C3—H3A	108.7
C6—C5—C2	106.4 (3)	C2—C3—H3A	108.7
C10—C5—C2	134.3 (3)	C4—C3—H3B	108.7
C1—C2—C5	106.9 (3)	C2—C3—H3B	108.7
C1—C2—C3	124.9 (3)	H3A—C3—H3B	107.6
C5—C2—C3	128.1 (3)	C10—C9—C8	119.2 (5)
O1—C10—C9	126.0 (4)	C10—C9—H9A	120.4
O1—C10—C5	115.0 (3)	C8—C9—H9A	120.4
C9—C10—C5	119.0 (4)	C8—C7—C6	115.7 (5)
C10—O1—C11	117.4 (4)	C8—C7—H7A	122.2
C6—N1—C1	109.7 (3)	C6—C7—H7A	122.2
C6—N1—H1A	125.2	C9—C8—C7	124.7 (4)
C1—N1—H1A	125.2	C9—C8—H8A	117.6
N1—C6—C5	107.3 (3)	C7—C8—H8A	117.6
N1—C6—C7	130.4 (4)	O1—C11—H11A	109.5
C5—C6—C7	122.2 (4)	O1—C11—H11B	109.5
N2—C4—C3	179.4 (4)	H11A—C11—H11B	109.5
C2—C1—N1	109.6 (3)	O1—C11—H11C	109.5
C2—C1—H1B	125.2	H11A—C11—H11C	109.5
N1—C1—H1B	125.2	H11B—C11—H11C	109.5
C4—C3—C2	114.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.86	2.19	3.028 (4)	164

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₂O
M_r	186.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.3182 (17), 13.062 (3), 9.3867 (19)
β (°)	101.53 (3)
V (Å³)	999.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
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	0.979, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	9998, 2283, 1235
R_int	0.109
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.088, 0.298, 1.07
No. of reflections	2283
No. of parameters	127
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.45

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	2.19	3.028 (4)	164

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

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