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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o97.
Published online 2009 December 9. doi:  10.1107/S1600536809052416
PMCID: PMC2980040

1-Meth­oxy-2-methyl-1H-benzo[f]indole-3-carbonitrile

Abstract

Apart from the methyl group of the meth­oxy fragment, the title compound, C15H12N2O, is almost planar (r.m.s. deviation = 0.045 Å); the C atom deviates from the mean plane by 1.216 (1) Å. In the crystal, π–π stacking [shortest centroid–centroid separation = 3.4652 (10) Å] and C—H(...)π inter­actions occur.

Related literature

For the synthesis, see: Du et al. (2008 [triangle]).

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Object name is e-66-00o97-scheme1.jpg

Experimental

Crystal data

  • C15H12N2O
  • M r = 236.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o97-efi1.jpg
  • a = 18.663 (4) Å
  • b = 7.3763 (15) Å
  • c = 18.589 (4) Å
  • β = 113.46 (3)°
  • V = 2347.6 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 113 K
  • 0.20 × 0.18 × 0.16 mm

Data collection

  • Rigaku Saturn CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.983, T max = 0.986
  • 11412 measured reflections
  • 2060 independent reflections
  • 1858 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.094
  • S = 1.04
  • 2060 reflections
  • 166 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.16 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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052416/hb5274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052416/hb5274Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound, (I), comprises of a benzo ring and its fused indole ring (Fig. 1). The aromatic skeleton is essentially planar.

In the crystal packing, π-π stacking interaction and C—H···π interaction help establish the molecular packing. The shortest centroid-centroid separation is 3.4652 (10) Å, which occurs between the pyrrole parts of the molecules.

Experimental

The compound was obtained according to the method of Du and his coworkers (2008). Colourless block of (I) was grown by slow evaporation of its ethanolic solution.

Refinement

All H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å)and refined as riding with Uiso(H) = 1.2Ueq(CH) or 1.5Ueq(CH3).

Figures

Fig. 1.
The molecular structure of (I) showing displacement ellipsoids drawn at the 50% probability level.

Crystal data

C15H12N2OF(000) = 992
Mr = 236.27Dx = 1.337 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3553 reflections
a = 18.663 (4) Åθ = 2.2–27.9°
b = 7.3763 (15) ŵ = 0.09 mm1
c = 18.589 (4) ÅT = 113 K
β = 113.46 (3)°Block, colourless
V = 2347.6 (8) Å30.20 × 0.18 × 0.16 mm
Z = 8

Data collection

Rigaku Saturn CCD diffractometer2060 independent reflections
Radiation source: rotating anode1858 reflections with I > 2σ(I)
confocalRint = 0.035
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.4°
ω and [var phi] scansh = −22→22
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −8→8
Tmin = 0.983, Tmax = 0.986l = −22→22
11412 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.094w = 1/[σ2(Fo2) + (0.0542P)2 + 1.1054P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2060 reflectionsΔρmax = 0.19 e Å3
166 parametersΔρmin = −0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0212 (18)

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
O10.43321 (5)0.84231 (12)0.08385 (5)0.0257 (3)
N10.35813 (6)0.90176 (14)0.06827 (6)0.0203 (3)
N20.11930 (6)1.14000 (15)−0.10753 (6)0.0269 (3)
C10.32134 (7)0.87498 (16)0.11865 (7)0.0194 (3)
C20.34992 (7)0.79261 (17)0.19296 (7)0.0223 (3)
H20.40100.75030.21630.027*
C30.29960 (7)0.77742 (16)0.22936 (7)0.0223 (3)
H30.31710.72480.27890.027*
C40.22060 (7)0.83997 (16)0.19371 (7)0.0201 (3)
C50.16852 (7)0.81573 (17)0.23131 (7)0.0235 (3)
H50.18610.75890.28000.028*
C60.09292 (7)0.87424 (18)0.19742 (7)0.0256 (3)
H60.05970.85790.22320.031*
C70.06515 (8)0.95940 (18)0.12338 (7)0.0249 (3)
H70.01381.00020.10080.030*
C80.11331 (7)0.98234 (16)0.08458 (7)0.0208 (3)
H80.09411.03720.03550.025*
C90.19198 (7)0.92382 (15)0.11816 (7)0.0181 (3)
C100.24518 (7)0.93956 (15)0.08037 (7)0.0181 (3)
C110.23885 (7)1.00368 (15)0.00486 (7)0.0185 (3)
C120.31010 (7)0.97803 (16)−0.00040 (7)0.0195 (3)
C130.33588 (8)1.02295 (18)−0.06433 (7)0.0253 (3)
H13A0.36311.1367−0.05310.038*
H13B0.29111.0317−0.11310.038*
H13C0.37000.9295−0.06810.038*
C140.48901 (8)0.9831 (2)0.12264 (9)0.0327 (4)
H14A0.48181.08290.08730.049*
H14B0.54100.93620.13830.049*
H14C0.48131.02390.16810.049*
C150.17262 (7)1.07923 (16)−0.05700 (7)0.0196 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0194 (5)0.0244 (5)0.0344 (5)0.0039 (4)0.0119 (4)−0.0008 (4)
N10.0163 (5)0.0211 (5)0.0235 (6)0.0016 (4)0.0079 (4)−0.0004 (4)
N20.0258 (6)0.0317 (7)0.0227 (6)0.0015 (5)0.0093 (5)0.0016 (5)
C10.0211 (6)0.0161 (6)0.0216 (6)−0.0016 (5)0.0090 (5)−0.0021 (5)
C20.0203 (6)0.0193 (6)0.0237 (7)0.0015 (5)0.0049 (5)−0.0005 (5)
C30.0274 (7)0.0180 (6)0.0190 (6)−0.0013 (5)0.0067 (5)0.0008 (5)
C40.0241 (7)0.0155 (6)0.0201 (6)−0.0031 (5)0.0082 (5)−0.0034 (5)
C50.0300 (7)0.0205 (6)0.0200 (6)−0.0063 (5)0.0100 (5)−0.0031 (5)
C60.0265 (7)0.0283 (7)0.0258 (7)−0.0094 (6)0.0145 (6)−0.0062 (5)
C70.0199 (6)0.0273 (7)0.0259 (7)−0.0043 (5)0.0076 (5)−0.0063 (5)
C80.0209 (6)0.0200 (6)0.0190 (6)−0.0034 (5)0.0054 (5)−0.0030 (5)
C90.0203 (6)0.0142 (6)0.0187 (6)−0.0042 (5)0.0067 (5)−0.0044 (5)
C100.0208 (6)0.0135 (6)0.0188 (6)−0.0030 (5)0.0065 (5)−0.0033 (5)
C110.0203 (6)0.0158 (6)0.0181 (6)−0.0023 (5)0.0064 (5)−0.0019 (4)
C120.0227 (7)0.0153 (6)0.0198 (6)−0.0026 (5)0.0076 (5)−0.0032 (5)
C130.0295 (7)0.0232 (7)0.0262 (7)−0.0014 (5)0.0143 (6)−0.0012 (5)
C140.0183 (7)0.0371 (8)0.0394 (8)−0.0031 (6)0.0079 (6)−0.0001 (6)
C150.0225 (7)0.0191 (6)0.0192 (6)−0.0034 (5)0.0104 (5)−0.0025 (5)

Geometric parameters (Å, °)

O1—N11.3844 (13)C6—H60.9300
O1—C141.4442 (16)C7—C81.3685 (18)
N1—C121.3559 (16)C7—H70.9300
N1—C11.3784 (16)C8—C91.4149 (18)
N2—C151.1529 (16)C8—H80.9300
C1—C101.3958 (17)C9—C101.4312 (17)
C1—C21.4054 (17)C10—C111.4408 (16)
C2—C31.3631 (19)C11—C121.3846 (18)
C2—H20.9300C11—C151.4245 (18)
C3—C41.4311 (18)C12—C131.4862 (17)
C3—H30.9300C13—H13A0.9600
C4—C51.4163 (18)C13—H13B0.9600
C4—C91.4292 (17)C13—H13C0.9600
C5—C61.3662 (19)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—C71.4106 (19)C14—H14C0.9600
N1—O1—C14110.19 (9)C9—C8—H8119.5
C12—N1—C1112.19 (10)C8—C9—C4118.80 (11)
C12—N1—O1124.28 (10)C8—C9—C10124.02 (11)
C1—N1—O1123.30 (10)C4—C9—C10117.16 (11)
N1—C1—C10106.64 (11)C1—C10—C9119.12 (11)
N1—C1—C2129.27 (11)C1—C10—C11106.30 (11)
C10—C1—C2124.03 (12)C9—C10—C11134.51 (11)
C3—C2—C1117.16 (11)C12—C11—C15123.07 (11)
C3—C2—H2121.4C12—C11—C10108.38 (11)
C1—C2—H2121.4C15—C11—C10128.54 (11)
C2—C3—C4122.01 (12)N1—C12—C11106.49 (11)
C2—C3—H3119.0N1—C12—C13122.83 (11)
C4—C3—H3119.0C11—C12—C13130.67 (12)
C5—C4—C9118.56 (11)C12—C13—H13A109.5
C5—C4—C3120.91 (11)C12—C13—H13B109.5
C9—C4—C3120.51 (11)H13A—C13—H13B109.5
C6—C5—C4121.21 (12)C12—C13—H13C109.5
C6—C5—H5119.4H13A—C13—H13C109.5
C4—C5—H5119.4H13B—C13—H13C109.5
C5—C6—C7120.10 (12)O1—C14—H14A109.5
C5—C6—H6120.0O1—C14—H14B109.5
C7—C6—H6120.0H14A—C14—H14B109.5
C8—C7—C6120.40 (12)O1—C14—H14C109.5
C8—C7—H7119.8H14A—C14—H14C109.5
C6—C7—H7119.8H14B—C14—H14C109.5
C7—C8—C9120.91 (12)N2—C15—C11179.39 (13)
C7—C8—H8119.5
C14—O1—N1—C1293.87 (13)N1—C1—C10—C9178.00 (10)
C14—O1—N1—C1−92.15 (13)C2—C1—C10—C90.53 (18)
C12—N1—C1—C10−0.59 (13)N1—C1—C10—C110.58 (12)
O1—N1—C1—C10−175.22 (10)C2—C1—C10—C11−176.89 (11)
C12—N1—C1—C2176.70 (12)C8—C9—C10—C1−179.17 (11)
O1—N1—C1—C22.08 (19)C4—C9—C10—C1−0.57 (16)
N1—C1—C2—C3−177.49 (11)C8—C9—C10—C11−2.7 (2)
C10—C1—C2—C3−0.62 (18)C4—C9—C10—C11175.95 (12)
C1—C2—C3—C40.78 (18)C1—C10—C11—C12−0.40 (13)
C2—C3—C4—C5177.32 (11)C9—C10—C11—C12−177.24 (12)
C2—C3—C4—C9−0.89 (18)C1—C10—C11—C15178.68 (11)
C9—C4—C5—C6−1.41 (18)C9—C10—C11—C151.8 (2)
C3—C4—C5—C6−179.65 (11)C1—N1—C12—C110.33 (13)
C4—C5—C6—C70.48 (19)O1—N1—C12—C11174.90 (10)
C5—C6—C7—C80.70 (19)C1—N1—C12—C13179.24 (11)
C6—C7—C8—C9−0.91 (18)O1—N1—C12—C13−6.20 (18)
C7—C8—C9—C4−0.04 (17)C15—C11—C12—N1−179.09 (10)
C7—C8—C9—C10178.54 (11)C10—C11—C12—N10.05 (13)
C5—C4—C9—C81.18 (17)C15—C11—C12—C132.1 (2)
C3—C4—C9—C8179.42 (10)C10—C11—C12—C13−178.73 (12)
C5—C4—C9—C10−177.50 (10)C12—C11—C15—N220 (14)
C3—C4—C9—C100.75 (17)C10—C11—C15—N2−159 (14)

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C4–C9 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg3i0.932.653.3956 (15)138

Symmetry codes: (i) x, −y−1, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5274).

References

  • Du, Y. F., Chang, J. B., Reiner, J. & Zhao, K. (2008). J. Org. Chem.73, 2007–2010. [PubMed]
  • Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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