organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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 [Ccy—Cme—Car—Car = 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[Ge, Y.-H., Pan, M.-L., Xu, J. & Luo, Y.-H. (2012). Acta Cryst. E68, o141.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10N2O

  • Mr = 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[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.979, Tmax = 0.988

  • 9998 measured reflections

  • 2283 independent reflections

  • 1235 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

All H atoms attached to C atoms and O atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (CH), C—H = 0.97 Å (CH2), C—H = 0.96 Å (CH3)and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(CH, CH2 and NH) and Uiso(H) = 1.5Ueq(CH3).

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-(4-Methoxy-1H-indol-3-yl)acetonitrile top
Crystal data top
C11H10N2OF(000) = 392
Mr = 186.21Dx = 1.238 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2283 reflections
a = 8.3182 (17) Åθ = 3.1–27.5°
b = 13.062 (3) ŵ = 0.08 mm1
c = 9.3867 (19) ÅT = 293 K
β = 101.53 (3)°Block, colourless
V = 999.3 (3) Å30.26 × 0.24 × 0.15 mm
Z = 4
Data collection top
Rigaku SCXmini CCD
diffractometer
2283 independent reflections
Radiation source: fine-focus sealed tube1235 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.109
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.1°
CCD_Profile_fitting scansh = 1010
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1616
Tmin = 0.979, Tmax = 0.988l = 1212
9998 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)] = 0.088Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.298H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1429P)2 + 0.1759P]
where P = (Fo2 + 2Fc2)/3
2283 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.38 e Å3
12 restraintsΔρmin = 0.45 e Å3
Crystal data top
C11H10N2OV = 999.3 (3) Å3
Mr = 186.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.3182 (17) ŵ = 0.08 mm1
b = 13.062 (3) ÅT = 293 K
c = 9.3867 (19) Å0.26 × 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)
Tmin = 0.979, Tmax = 0.988Rint = 0.109
9998 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.08812 restraints
wR(F2) = 0.298H-atom parameters constrained
S = 1.07Δρmax = 0.38 e Å3
2283 reflectionsΔρmin = 0.45 e Å3
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
xyzUiso*/Ueq
C50.4959 (3)0.6202 (2)0.1157 (3)0.0567 (7)
C20.4374 (4)0.6934 (2)0.0033 (3)0.0610 (8)
C100.4215 (5)0.5425 (2)0.1837 (3)0.0724 (9)
O10.2566 (3)0.53144 (18)0.1335 (3)0.0941 (9)
N10.7052 (4)0.7163 (3)0.0794 (4)0.0927 (11)
H1A0.80200.74150.08640.111*
C60.6656 (4)0.6374 (3)0.1600 (4)0.0770 (10)
N20.0524 (4)0.7726 (3)0.0570 (4)0.0978 (11)
C40.1475 (4)0.7424 (3)0.0049 (4)0.0760 (10)
C10.5681 (5)0.7495 (3)0.0147 (4)0.0811 (10)
H1B0.56530.80270.08100.097*
C30.2684 (4)0.7039 (3)0.0858 (3)0.0806 (10)
H3A0.27200.75010.16610.097*
H3B0.23230.63760.12660.097*
C90.5176 (6)0.4845 (3)0.2916 (5)0.1116 (12)
H9A0.47080.43290.33820.134*
C70.7644 (6)0.5791 (3)0.2705 (4)0.1120 (12)
H7A0.87620.59120.30070.134*
C80.6861 (6)0.5044 (4)0.3297 (5)0.1123 (11)
H8A0.74860.46340.40080.135*
C110.1740 (7)0.4533 (4)0.1992 (6)0.141 (2)
H11A0.05940.45350.15530.212*
H11B0.18720.46640.30150.212*
H11C0.22030.38770.18460.212*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C50.0627 (17)0.0571 (15)0.0523 (15)0.0009 (12)0.0163 (12)0.0114 (12)
C20.0707 (18)0.0654 (17)0.0507 (15)0.0105 (13)0.0213 (13)0.0056 (13)
C100.099 (2)0.0579 (17)0.0641 (19)0.0040 (16)0.0265 (18)0.0044 (13)
O10.107 (2)0.0782 (16)0.1058 (19)0.0287 (13)0.0425 (16)0.0047 (13)
N10.0673 (18)0.104 (2)0.116 (3)0.0194 (16)0.0396 (18)0.041 (2)
C60.074 (2)0.082 (2)0.077 (2)0.0092 (17)0.0204 (17)0.0287 (18)
N20.0590 (17)0.125 (3)0.104 (3)0.0091 (17)0.0054 (17)0.009 (2)
C40.0611 (19)0.089 (2)0.071 (2)0.0100 (17)0.0037 (16)0.0014 (17)
C10.097 (3)0.077 (2)0.082 (2)0.0183 (18)0.048 (2)0.0083 (17)
C30.086 (2)0.098 (2)0.0561 (18)0.0022 (18)0.0085 (16)0.0000 (16)
C90.146 (2)0.0971 (19)0.0851 (18)0.054 (2)0.0086 (18)0.0107 (15)
C70.140 (3)0.102 (2)0.0871 (18)0.058 (2)0.0063 (18)0.0196 (15)
C80.145 (2)0.0994 (19)0.0859 (17)0.059 (2)0.0063 (17)0.0142 (14)
C110.195 (5)0.090 (3)0.167 (5)0.063 (3)0.105 (4)0.013 (3)
Geometric parameters (Å, º) top
C5—C61.407 (4)C4—C31.465 (6)
C5—C101.407 (4)C1—H1B0.9300
C5—C21.435 (4)C3—H3A0.9700
C2—C11.350 (4)C3—H3B0.9700
C2—C31.492 (4)C9—C81.400 (7)
C10—O11.365 (4)C9—H9A0.9300
C10—C91.384 (5)C7—C81.353 (7)
O1—C111.437 (4)C7—H7A0.9300
N1—C61.357 (5)C8—H8A0.9300
N1—C11.366 (5)C11—H11A0.9600
N1—H1A0.8600C11—H11B0.9600
C6—C71.411 (5)C11—H11C0.9600
N2—C41.142 (5)
C6—C5—C10119.2 (3)C4—C3—H3A108.7
C6—C5—C2106.4 (3)C2—C3—H3A108.7
C10—C5—C2134.3 (3)C4—C3—H3B108.7
C1—C2—C5106.9 (3)C2—C3—H3B108.7
C1—C2—C3124.9 (3)H3A—C3—H3B107.6
C5—C2—C3128.1 (3)C10—C9—C8119.2 (5)
O1—C10—C9126.0 (4)C10—C9—H9A120.4
O1—C10—C5115.0 (3)C8—C9—H9A120.4
C9—C10—C5119.0 (4)C8—C7—C6115.7 (5)
C10—O1—C11117.4 (4)C8—C7—H7A122.2
C6—N1—C1109.7 (3)C6—C7—H7A122.2
C6—N1—H1A125.2C9—C8—C7124.7 (4)
C1—N1—H1A125.2C9—C8—H8A117.6
N1—C6—C5107.3 (3)C7—C8—H8A117.6
N1—C6—C7130.4 (4)O1—C11—H11A109.5
C5—C6—C7122.2 (4)O1—C11—H11B109.5
N2—C4—C3179.4 (4)H11A—C11—H11B109.5
C2—C1—N1109.6 (3)O1—C11—H11C109.5
C2—C1—H1B125.2H11A—C11—H11C109.5
N1—C1—H1B125.2H11B—C11—H11C109.5
C4—C3—C2114.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.193.028 (4)164
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC11H10N2O
Mr186.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.3182 (17), 13.062 (3), 9.3867 (19)
β (°) 101.53 (3)
V3)999.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.26 × 0.24 × 0.15
Data collection
DiffractometerRigaku SCXmini CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.979, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
9998, 2283, 1235
Rint0.109
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.088, 0.298, 1.07
No. of reflections2283
No. of parameters127
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.193.028 (4)164
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

We thank Southeast University for support.

References

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

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ISSN: 2056-9890
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