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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890

2-(7-Methyl-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: 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 [Ccy—Cme—Car—Car = 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[Kunzer, A. R. & Wendt, M. D. (2011). Tetrahedron, 52, 1815-1818.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10N2

  • Mr = 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[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.981, Tmax = 0.989

  • 9402 measured reflections

  • 2160 independent reflections

  • 1418 reflections with I > 2σ(I)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.154

  • S = 1.05

  • 2160 reflections

  • 118 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.17 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 2.24 3.022 (2) 151
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

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 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.

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 with hydrogen bonds shown as dashed lines.
2-(7-Methyl-1H-indol-3-yl)acetonitrile top
Crystal data top
C11H10N2F(000) = 360
Mr = 170.21Dx = 1.184 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2175 reflections
a = 6.9962 (14) Åθ = 2.7–27.5°
b = 8.9445 (18) ŵ = 0.07 mm1
c = 15.406 (3) ÅT = 293 K
β = 97.97 (3)°Block, colourless
V = 954.7 (3) Å30.26 × 0.24 × 0.15 mm
Z = 4
Data collection top
Rigaku SCXmini CCD
diffractometer
2160 independent reflections
Radiation source: fine-focus sealed tube1418 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω scansθmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
h = 99
Tmin = 0.981, Tmax = 0.989k = 1111
9402 measured reflectionsl = 1919
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0708P)2 + 0.0707P]
where P = (Fo2 + 2Fc2)/3
2160 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C11H10N2V = 954.7 (3) Å3
Mr = 170.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.9962 (14) ŵ = 0.07 mm1
b = 8.9445 (18) ÅT = 293 K
c = 15.406 (3) Å0.26 × 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)
Tmin = 0.981, Tmax = 0.989Rint = 0.058
9402 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.05Δρmax = 0.16 e Å3
2160 reflectionsΔρmin = 0.17 e Å3
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
xyzUiso*/Ueq
C10.0179 (3)0.6121 (2)0.21424 (12)0.0587 (5)
H1B0.12780.66420.19030.070*
C20.0270 (2)0.57655 (18)0.30000 (11)0.0511 (4)
C30.2072 (2)0.49843 (17)0.30912 (10)0.0473 (4)
C40.3276 (3)0.43296 (19)0.37953 (12)0.0613 (5)
H4A0.29550.43690.43610.074*
C50.4936 (3)0.3631 (2)0.36311 (16)0.0758 (6)
H5A0.57360.31870.40920.091*
C60.5451 (3)0.3571 (2)0.27861 (17)0.0768 (6)
H6A0.65880.30880.27030.092*
C70.4334 (3)0.4204 (2)0.20730 (13)0.0644 (5)
C80.2629 (2)0.48979 (17)0.22467 (10)0.0506 (4)
C90.4896 (4)0.4170 (3)0.11583 (16)0.0958 (8)
H9A0.60910.36390.11680.144*
H9B0.50470.51750.09590.144*
H9C0.39050.36760.07680.144*
C100.0948 (3)0.6089 (2)0.37116 (13)0.0678 (5)
H10A0.21710.65090.34490.081*
H10B0.12160.51580.39940.081*
C110.0021 (3)0.7128 (2)0.43771 (12)0.0621 (5)
N10.1212 (2)0.56067 (16)0.16799 (9)0.0600 (4)
H1A0.12070.57070.11240.072*
N20.0698 (3)0.7913 (2)0.48993 (11)0.0856 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0586 (10)0.0557 (10)0.0580 (11)0.0065 (8)0.0048 (9)0.0008 (8)
C20.0529 (9)0.0500 (9)0.0495 (10)0.0010 (7)0.0040 (7)0.0038 (7)
C30.0537 (9)0.0413 (8)0.0454 (9)0.0049 (7)0.0021 (7)0.0014 (6)
C40.0659 (11)0.0584 (11)0.0562 (10)0.0058 (9)0.0030 (9)0.0094 (8)
C50.0656 (12)0.0597 (12)0.0951 (16)0.0036 (10)0.0131 (11)0.0164 (11)
C60.0601 (12)0.0574 (12)0.1126 (18)0.0064 (9)0.0108 (12)0.0067 (12)
C70.0642 (11)0.0542 (11)0.0780 (13)0.0045 (9)0.0207 (10)0.0131 (9)
C80.0585 (10)0.0425 (9)0.0503 (9)0.0045 (7)0.0055 (8)0.0040 (7)
C90.0977 (17)0.0985 (17)0.1011 (18)0.0132 (14)0.0481 (14)0.0277 (13)
C100.0606 (11)0.0731 (12)0.0715 (12)0.0027 (9)0.0156 (10)0.0097 (10)
C110.0675 (11)0.0716 (12)0.0490 (10)0.0085 (10)0.0150 (9)0.0013 (9)
N10.0748 (10)0.0628 (9)0.0404 (8)0.0020 (8)0.0012 (7)0.0008 (6)
N20.1026 (14)0.0986 (14)0.0549 (10)0.0050 (11)0.0087 (9)0.0152 (9)
Geometric parameters (Å, º) top
C1—C21.353 (2)C6—H6A0.9300
C1—N11.364 (2)C7—C81.403 (2)
C1—H1B0.9300C7—C91.515 (3)
C2—C31.431 (2)C8—N11.381 (2)
C2—C101.507 (2)C9—H9A0.9600
C3—C41.405 (2)C9—H9B0.9600
C3—C81.411 (2)C9—H9C0.9600
C4—C51.373 (3)C10—C111.467 (3)
C4—H4A0.9300C10—H10A0.9700
C5—C61.399 (3)C10—H10B0.9700
C5—H5A0.9300C11—N21.131 (2)
C6—C71.378 (3)N1—H1A0.8600
C2—C1—N1110.17 (15)C8—C7—C9121.5 (2)
C2—C1—H1B124.9N1—C8—C7129.60 (17)
N1—C1—H1B124.9N1—C8—C3106.97 (15)
C1—C2—C3107.04 (15)C7—C8—C3123.43 (17)
C1—C2—C10125.94 (16)C7—C9—H9A109.5
C3—C2—C10126.99 (15)C7—C9—H9B109.5
C4—C3—C8118.43 (16)H9A—C9—H9B109.5
C4—C3—C2134.80 (16)C7—C9—H9C109.5
C8—C3—C2106.76 (14)H9A—C9—H9C109.5
C5—C4—C3118.63 (18)H9B—C9—H9C109.5
C5—C4—H4A120.7C11—C10—C2112.97 (15)
C3—C4—H4A120.7C11—C10—H10A109.0
C4—C5—C6121.50 (19)C2—C10—H10A109.0
C4—C5—H5A119.2C11—C10—H10B109.0
C6—C5—H5A119.2C2—C10—H10B109.0
C7—C6—C5122.37 (19)H10A—C10—H10B107.8
C7—C6—H6A118.8N2—C11—C10179.0 (2)
C5—C6—H6A118.8C1—N1—C8109.06 (14)
C6—C7—C8115.63 (18)C1—N1—H1A125.5
C6—C7—C9122.82 (19)C8—N1—H1A125.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.243.022 (2)151
Symmetry code: (i) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC11H10N2
Mr170.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)6.9962 (14), 8.9445 (18), 15.406 (3)
β (°) 97.97 (3)
V3)954.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.26 × 0.24 × 0.15
Data collection
DiffractometerRigaku SCXmini CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.981, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
9402, 2160, 1418
Rint0.058
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.154, 1.05
No. of reflections2160
No. of parameters118
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.243.022 (2)151
Symmetry code: (i) x, y+3/2, z1/2.
 

Acknowledgements

We thank Southeast University for support.

References

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