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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1759.
Published online 2009 July 4. doi:  10.1107/S1600536809024817
PMCID: PMC2977218

1,3-Dimethyl-1H-indole-2-carbonitrile

Abstract

The title compound, C11H10N2, crystallizes with two mol­ecules in the asymmetric unit, both of which are essentially planar (r.m.s. deviations = 0.014 and 0.016 Å). In the crystal, aromatic π–π stacking inter­actions occur [shortest centroid–centroid separation = 3.5569 (11) Å].

Related literature

For the synthesis, see: Snyder & Eliel (1948 [triangle]).

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Object name is e-65-o1759-scheme1.jpg

Experimental

Crystal data

  • C11H10N2
  • M r = 170.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1759-efi1.jpg
  • a = 8.8066 (18) Å
  • b = 15.359 (3) Å
  • c = 13.480 (3) Å
  • β = 95.67 (3)°
  • V = 1814.4 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 113 K
  • 0.20 × 0.18 × 0.14 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.985, T max = 0.990
  • 16175 measured reflections
  • 4303 independent reflections
  • 3462 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.132
  • S = 1.03
  • 4303 reflections
  • 238 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024817/hb5013sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024817/hb5013Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The asymmetric unit of (I) comprises of two molecules (Fig. 1), in which the indole ring is each almost coplanar with a dihedral angle of 1.32 (7)° and 0.75 (7)°, respectively, between its pyrrole ring and fused benzene ring.

In the crystal packing, strong π-π stacking interactions help establishing the molecular packing.

Experimental

The title compound was prepared according to the modified method of Snyder & Eliel (1948), as Scheme 1 shows. 1-Methyl-3-dimethylaminomethylindole was added to an ethanolic-aqueous solution (15%, 100 ml) of sodium cyanide (1.87 g, 0.038 mol), and then the resulting mixture was refluxed for 2 h, with the process monitored by TLC. After the reaction ceased, the reaction mixture was extracted with CH2Cl2 (3 × 50 ml), dried over anhydrous Na2SO4, and separated by flash chromatograhpy (ethyl acetate-petroleum 10/90 v/v) to provide the major product 1-methylindole-3-acetonitrile (yield 3.68 g,57%, m.p.328–330 K) and its isomeric substance 1,3-dimethyl-1H-indole-2-carbonitrile (yield 0.97 g,15%, m.p.339–340 K). Colourless blocks of (I) were grown from a mixture of ethyl actate and petroleum ether (1:1 v/v).

Refinement

All H atoms were positioned geometrically (C—H = 0.95–0.98 Å)and refined as riding with Uiso(H) = 1.2Ueq(CH) or 1.5Ueq(CH3).

Figures

Fig. 1.
The two molecular structure of (I) in the asymmetrical unit with the atom-numbering scheme and 50% probability displacement ellipsoids.
Fig. 2.
The formation of the title compound.

Crystal data

C11H10N2F(000) = 720
Mr = 170.21Dx = 1.246 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5208 reflections
a = 8.8066 (18) Åθ = 2.0–27.9°
b = 15.359 (3) ŵ = 0.08 mm1
c = 13.480 (3) ÅT = 113 K
β = 95.67 (3)°Block, colourless
V = 1814.4 (7) Å30.20 × 0.18 × 0.14 mm
Z = 8

Data collection

Rigaku Saturn CCD area-detector diffractometer4303 independent reflections
Radiation source: rotating anode3462 reflections with I > 2σ(I)
confoclaRint = 0.035
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.0°
ω and [var phi] scansh = −11→7
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −20→20
Tmin = 0.985, Tmax = 0.990l = −17→17
16175 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0783P)2 + 0.2443P] where P = (Fo2 + 2Fc2)/3
4303 reflections(Δ/σ)max = 0.003
238 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

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)

xyzUiso*/Ueq
N10.82816 (12)0.53565 (7)0.89373 (8)0.0220 (2)
N20.54466 (13)0.37505 (8)0.91305 (9)0.0323 (3)
N30.68373 (12)0.02746 (7)0.89897 (8)0.0234 (3)
N40.88484 (17)−0.16898 (9)0.90325 (11)0.0447 (4)
C10.94864 (16)0.30650 (8)0.85689 (11)0.0294 (3)
H1A1.01430.28410.91420.044*
H1B0.99500.29360.79540.044*
H1C0.84820.27860.85440.044*
C20.93090 (14)0.40280 (8)0.86704 (9)0.0210 (3)
C31.04387 (14)0.46744 (8)0.85879 (9)0.0201 (3)
C41.19845 (15)0.46347 (8)0.84089 (9)0.0237 (3)
H41.24620.40920.83080.028*
C51.27868 (15)0.54002 (9)0.83840 (10)0.0286 (3)
H51.38340.53820.82710.034*
C61.20941 (16)0.62085 (9)0.85218 (10)0.0285 (3)
H61.26800.67250.84880.034*
C71.05797 (15)0.62722 (8)0.87060 (9)0.0247 (3)
H71.01140.68200.88000.030*
C80.97653 (14)0.54941 (8)0.87480 (9)0.0200 (3)
C90.80186 (14)0.44673 (8)0.88817 (9)0.0211 (3)
C100.65833 (15)0.40909 (8)0.90293 (10)0.0242 (3)
C110.71576 (15)0.60235 (9)0.91016 (10)0.0278 (3)
H11A0.76640.65140.94630.042*
H11B0.63820.57790.94950.042*
H11C0.66700.62260.84580.042*
C120.43756 (19)−0.16808 (9)0.85253 (11)0.0339 (3)
H12A0.4196−0.18010.78250.051*
H12B0.3426−0.16990.88180.051*
H12C0.5057−0.21100.88370.051*
C130.50716 (16)−0.07991 (8)0.86744 (9)0.0239 (3)
C140.43132 (15)0.00185 (8)0.86448 (9)0.0223 (3)
C150.27685 (15)0.02613 (9)0.84775 (9)0.0258 (3)
H150.1994−0.01670.83520.031*
C160.24020 (16)0.11338 (9)0.85001 (10)0.0280 (3)
H160.13630.13070.83920.034*
C170.35452 (16)0.17728 (9)0.86808 (10)0.0277 (3)
H170.32580.23690.86890.033*
C180.50620 (16)0.15567 (8)0.88453 (10)0.0244 (3)
H180.58270.19910.89610.029*
C190.54362 (14)0.06698 (8)0.88352 (9)0.0205 (3)
C200.66012 (16)−0.06165 (8)0.88826 (9)0.0241 (3)
C210.78416 (17)−0.12122 (9)0.89733 (11)0.0306 (3)
C220.83057 (15)0.07062 (9)0.91704 (11)0.0300 (3)
H22A0.84960.10530.85850.045*
H22B0.91120.02680.92950.045*
H22C0.83010.10880.97530.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0207 (5)0.0209 (5)0.0245 (6)0.0012 (4)0.0027 (4)−0.0009 (4)
N20.0231 (6)0.0319 (6)0.0425 (7)−0.0034 (5)0.0063 (5)−0.0043 (5)
N30.0229 (6)0.0213 (5)0.0262 (6)0.0001 (4)0.0027 (4)0.0008 (4)
N40.0502 (9)0.0360 (7)0.0480 (9)0.0171 (7)0.0053 (7)0.0000 (6)
C10.0278 (7)0.0219 (6)0.0387 (8)0.0004 (5)0.0039 (6)0.0009 (5)
C20.0196 (6)0.0219 (6)0.0211 (6)−0.0003 (5)0.0001 (5)0.0009 (5)
C30.0202 (6)0.0211 (6)0.0189 (6)−0.0001 (5)0.0007 (5)0.0012 (4)
C40.0210 (6)0.0268 (6)0.0232 (6)0.0013 (5)0.0023 (5)0.0017 (5)
C50.0211 (6)0.0385 (8)0.0264 (7)−0.0046 (6)0.0028 (5)0.0034 (6)
C60.0296 (7)0.0278 (7)0.0277 (7)−0.0104 (6)0.0010 (6)0.0027 (5)
C70.0283 (7)0.0212 (6)0.0242 (7)−0.0019 (5)0.0008 (5)−0.0004 (5)
C80.0202 (6)0.0220 (6)0.0174 (6)0.0005 (5)0.0001 (5)0.0007 (4)
C90.0199 (6)0.0222 (6)0.0210 (6)−0.0018 (5)0.0011 (5)0.0010 (5)
C100.0226 (6)0.0245 (6)0.0254 (7)0.0011 (5)0.0022 (5)−0.0022 (5)
C110.0246 (7)0.0275 (6)0.0321 (7)0.0058 (5)0.0064 (6)−0.0014 (5)
C120.0435 (9)0.0250 (7)0.0330 (8)−0.0067 (6)0.0024 (6)−0.0010 (5)
C130.0305 (7)0.0211 (6)0.0201 (6)−0.0028 (5)0.0028 (5)0.0001 (5)
C140.0252 (7)0.0236 (6)0.0182 (6)−0.0034 (5)0.0030 (5)−0.0010 (5)
C150.0237 (7)0.0317 (7)0.0220 (7)−0.0034 (6)0.0015 (5)−0.0013 (5)
C160.0234 (7)0.0355 (7)0.0248 (7)0.0037 (6)0.0013 (5)0.0005 (5)
C170.0300 (7)0.0254 (6)0.0276 (7)0.0055 (6)0.0024 (6)0.0018 (5)
C180.0266 (7)0.0213 (6)0.0252 (7)−0.0016 (5)0.0019 (5)0.0010 (5)
C190.0204 (6)0.0220 (6)0.0192 (6)−0.0001 (5)0.0018 (5)0.0009 (4)
C200.0296 (7)0.0200 (6)0.0231 (6)0.0026 (5)0.0045 (5)0.0013 (5)
C210.0382 (8)0.0249 (6)0.0292 (7)0.0052 (6)0.0053 (6)−0.0001 (5)
C220.0216 (7)0.0292 (7)0.0384 (8)−0.0025 (6)−0.0013 (6)0.0030 (6)

Geometric parameters (Å, °)

N1—C81.3722 (16)C9—C101.4217 (17)
N1—C91.3860 (16)C11—H11A0.9800
N1—C111.4566 (16)C11—H11B0.9800
N2—C101.1493 (17)C11—H11C0.9800
N3—C191.3724 (16)C12—C131.4917 (18)
N3—C201.3897 (16)C12—H12A0.9600
N3—C221.4522 (17)C12—H12B0.9600
N4—C211.1474 (19)C12—H12C0.9600
C1—C21.4949 (17)C13—C201.3774 (19)
C1—H1A0.9800C13—C141.4211 (18)
C1—H1B0.9800C14—C151.4071 (19)
C1—H1C0.9800C14—C191.4123 (18)
C2—C91.3754 (17)C15—C161.3794 (19)
C2—C31.4177 (17)C15—H150.9500
C3—C41.4072 (18)C16—C171.410 (2)
C3—C81.4172 (17)C16—H160.9500
C4—C51.3739 (19)C17—C181.3730 (19)
C4—H40.9500C17—H170.9500
C5—C61.404 (2)C18—C191.4019 (17)
C5—H50.9500C18—H180.9500
C6—C71.384 (2)C20—C211.4209 (19)
C6—H60.9500C22—H22A0.9800
C7—C81.3978 (17)C22—H22B0.9800
C7—H70.9500C22—H22C0.9800
C8—N1—C9107.39 (10)N1—C11—H11C109.5
C8—N1—C11126.43 (11)H11A—C11—H11C109.5
C9—N1—C11126.07 (11)H11B—C11—H11C109.5
C19—N3—C20107.26 (11)C13—C12—H12A109.4
C19—N3—C22126.58 (11)C13—C12—H12B109.5
C20—N3—C22126.05 (11)H12A—C12—H12B109.5
C2—C1—H1A109.5C13—C12—H12C109.5
C2—C1—H1B109.5H12A—C12—H12C109.5
H1A—C1—H1B109.5H12B—C12—H12C109.5
C2—C1—H1C109.5C20—C13—C14105.86 (11)
H1A—C1—H1C109.5C20—C13—C12126.36 (12)
H1B—C1—H1C109.5C14—C13—C12127.78 (13)
C9—C2—C3105.86 (11)C15—C14—C19119.34 (12)
C9—C2—C1126.89 (12)C15—C14—C13133.08 (12)
C3—C2—C1127.24 (11)C19—C14—C13107.58 (12)
C4—C3—C8119.41 (11)C16—C15—C14118.59 (12)
C4—C3—C2132.95 (11)C16—C15—H15120.7
C8—C3—C2107.62 (11)C14—C15—H15120.7
C5—C4—C3118.40 (12)C15—C16—C17121.03 (13)
C5—C4—H4120.8C15—C16—H16119.5
C3—C4—H4120.8C17—C16—H16119.5
C4—C5—C6121.49 (13)C18—C17—C16121.76 (12)
C4—C5—H5119.3C18—C17—H17119.1
C6—C5—H5119.3C16—C17—H17119.1
C7—C6—C5121.70 (12)C17—C18—C19117.34 (12)
C7—C6—H6119.2C17—C18—H18121.3
C5—C6—H6119.2C19—C18—H18121.3
C6—C7—C8117.01 (12)N3—C19—C18129.57 (12)
C6—C7—H7121.5N3—C19—C14108.50 (11)
C8—C7—H7121.5C18—C19—C14121.94 (12)
N1—C8—C7129.87 (11)C13—C20—N3110.79 (11)
N1—C8—C3108.18 (10)C13—C20—C21127.91 (12)
C7—C8—C3121.96 (12)N3—C20—C21121.29 (12)
C2—C9—N1110.94 (11)N4—C21—C20178.97 (16)
C2—C9—C10126.43 (12)N3—C22—H22A109.5
N1—C9—C10122.63 (11)N3—C22—H22B109.5
N2—C10—C9176.77 (14)H22A—C22—H22B109.5
N1—C11—H11A109.5N3—C22—H22C109.5
N1—C11—H11B109.5H22A—C22—H22C109.5
H11A—C11—H11B109.5H22B—C22—H22C109.5
C9—C2—C3—C4178.15 (14)C20—C13—C14—C15−179.38 (13)
C1—C2—C3—C4−0.8 (2)C12—C13—C14—C15−0.1 (2)
C9—C2—C3—C8−0.48 (14)C20—C13—C14—C190.25 (14)
C1—C2—C3—C8−179.42 (12)C12—C13—C14—C19179.58 (13)
C8—C3—C4—C5−0.77 (19)C19—C14—C15—C160.34 (18)
C2—C3—C4—C5−179.27 (13)C13—C14—C15—C16179.94 (13)
C3—C4—C5—C6−0.7 (2)C14—C15—C16—C170.36 (19)
C4—C5—C6—C71.1 (2)C15—C16—C17—C18−0.3 (2)
C5—C6—C7—C8−0.1 (2)C16—C17—C18—C19−0.5 (2)
C9—N1—C8—C7179.28 (12)C20—N3—C19—C18−178.96 (13)
C11—N1—C8—C72.9 (2)C22—N3—C19—C18−2.4 (2)
C9—N1—C8—C3−0.91 (14)C20—N3—C19—C140.89 (14)
C11—N1—C8—C3−177.24 (11)C22—N3—C19—C14177.41 (12)
C6—C7—C8—N1178.39 (12)C17—C18—C19—N3−178.95 (12)
C6—C7—C8—C3−1.40 (19)C17—C18—C19—C141.23 (19)
C4—C3—C8—N1−177.98 (11)C15—C14—C19—N3178.98 (11)
C2—C3—C8—N10.87 (14)C13—C14—C19—N3−0.71 (14)
C4—C3—C8—C71.85 (19)C15—C14—C19—C18−1.17 (19)
C2—C3—C8—C7−179.30 (11)C13—C14—C19—C18179.14 (11)
C3—C2—C9—N1−0.08 (14)C14—C13—C20—N30.30 (14)
C1—C2—C9—N1178.86 (12)C12—C13—C20—N3−179.04 (12)
C3—C2—C9—C10179.90 (12)C14—C13—C20—C21−178.78 (13)
C1—C2—C9—C10−1.2 (2)C12—C13—C20—C211.9 (2)
C8—N1—C9—C20.62 (14)C19—N3—C20—C13−0.75 (14)
C11—N1—C9—C2176.97 (12)C22—N3—C20—C13−177.29 (12)
C8—N1—C9—C10−179.36 (11)C19—N3—C20—C21178.41 (12)
C11—N1—C9—C10−3.01 (19)C22—N3—C20—C211.86 (19)
C2—C9—C10—N2−13 (3)C13—C20—C21—N4103 (10)
N1—C9—C10—N2167 (3)N3—C20—C21—N4−76 (10)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5013).

References

  • Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Snyder, H. R. & Eliel, E. L. (1948). J. Am. Chem. Soc.70, 1703–1705. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography