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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o111.
Published online 2009 December 12. doi:  10.1107/S1600536809052441
PMCID: PMC2980008

2-Methyl-3-p-tolyl-3H-benzo[e]indole-1-carbonitrile

Abstract

In the title compound, C21H16N2, the dihedral angle between the benzoindole and tosyl ring systems is 71.99 (7)°. In the crystal, mol­ecules are linked into centrosymmetric dimers by pairs of C—H(...)N hydrogen bonds, generating R 2 2(16) loops.

Related literature

For the synthesis, see: Du et al. (2006 [triangle]).

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Object name is e-66-0o111-scheme1.jpg

Experimental

Crystal data

  • C21H16N2
  • M r = 296.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o111-efi1.jpg
  • a = 10.321 (2) Å
  • b = 12.422 (3) Å
  • c = 13.258 (3) Å
  • β = 107.14 (3)°
  • V = 1624.4 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 293 K
  • 0.28 × 0.20 × 0.18 mm

Data collection

  • Rigaku Saturn CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.980, T max = 0.987
  • 10714 measured reflections
  • 2858 independent reflections
  • 2092 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.168
  • S = 1.04
  • 2858 reflections
  • 210 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/S1600536809052441/hb5275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052441/hb5275Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound, (I), comprises of a benzoindole ring and tosyl ring (Fig. 1). The dihedral angle of both rings is 71.99 (7)°.

In the crystal packing, molecules are linked into centrosymmetric dimers by C—H···N hydrogen bonds (Table 1). Weak C—H···π interactions help dimers pack. No significant π-π stacking interaction was observed.

Experimental

The compound was obtained according to the method of Du and his coworkers (2006). 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 molecule of (I) showing displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
Centrosymmetric dimers of (I) formed by C—H···N hydrogen bonds drawn as dashed lines.

Crystal data

C21H16N2F(000) = 624
Mr = 296.36Dx = 1.212 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3474 reflections
a = 10.321 (2) Åθ = 2.2–27.5°
b = 12.422 (3) ŵ = 0.07 mm1
c = 13.258 (3) ÅT = 293 K
β = 107.14 (3)°Block, colourless
V = 1624.4 (6) Å30.28 × 0.20 × 0.18 mm
Z = 4

Data collection

Rigaku Saturn CCD diffractometer2858 independent reflections
Radiation source: rotating anode2092 reflections with I > 2σ(I)
confocalRint = 0.036
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.2°
ω and [var phi] scansh = −12→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −13→14
Tmin = 0.980, Tmax = 0.987l = −15→14
10714 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)] = 0.056H-atom parameters constrained
wR(F2) = 0.168w = 1/[σ2(Fo2) + (0.1027P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2858 reflectionsΔρmax = 0.19 e Å3
210 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: 0.070 (10)

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
N10.10089 (15)0.87702 (12)0.23973 (11)0.0575 (5)
N2−0.2675 (2)1.06928 (18)0.01735 (16)0.1025 (8)
C10.00439 (18)0.79674 (14)0.23281 (13)0.0547 (5)
C20.0217 (2)0.69469 (15)0.27979 (14)0.0629 (5)
H20.10530.67280.32410.075*
C3−0.0883 (2)0.62878 (16)0.25826 (15)0.0679 (6)
H3−0.07900.56060.28850.081*
C4−0.2171 (2)0.66084 (17)0.19091 (15)0.0631 (6)
C5−0.3298 (2)0.5901 (2)0.16630 (16)0.0806 (7)
H5−0.31970.52110.19470.097*
C6−0.4540 (2)0.6220 (2)0.10095 (19)0.0900 (8)
H6−0.52660.57420.08540.108*
C7−0.4715 (2)0.7253 (2)0.05799 (18)0.0860 (7)
H7−0.55610.74670.01500.103*
C8−0.3656 (2)0.79452 (19)0.07884 (15)0.0692 (6)
H8−0.37830.86300.04910.083*
C9−0.23647 (19)0.76498 (16)0.14464 (13)0.0580 (5)
C10−0.12000 (19)0.83318 (14)0.16682 (12)0.0542 (5)
C11−0.0941 (2)0.93897 (14)0.13370 (13)0.0589 (5)
C120.0402 (2)0.96343 (15)0.17945 (14)0.0608 (5)
C130.1146 (3)1.06418 (17)0.17368 (17)0.0812 (7)
H13A0.15461.09180.24360.122*
H13B0.05291.11640.13230.122*
H13C0.18471.04960.14140.122*
C14−0.1898 (2)1.01126 (18)0.06895 (15)0.0722 (6)
C150.24140 (19)0.86902 (14)0.29878 (14)0.0556 (5)
C160.3392 (2)0.85881 (17)0.24716 (15)0.0670 (6)
H160.31460.85690.17380.080*
C170.4734 (2)0.85143 (16)0.30554 (17)0.0722 (6)
H170.53880.84420.27040.087*
C180.5142 (2)0.85442 (15)0.41425 (17)0.0670 (6)
C190.4147 (2)0.86356 (17)0.46373 (16)0.0717 (6)
H190.43950.86470.53710.086*
C200.2793 (2)0.87108 (16)0.40767 (14)0.0661 (6)
H200.21400.87750.44300.079*
C210.6620 (2)0.8465 (2)0.4766 (2)0.1000 (9)
H21A0.69520.77590.46820.150*
H21B0.67200.85940.54990.150*
H21C0.71280.89930.45130.150*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0540 (10)0.0542 (9)0.0598 (9)0.0010 (7)0.0098 (7)0.0032 (7)
N20.1048 (18)0.1026 (16)0.0931 (13)0.0401 (13)0.0185 (12)0.0307 (12)
C10.0532 (11)0.0564 (11)0.0521 (9)0.0020 (9)0.0115 (8)0.0003 (8)
C20.0582 (12)0.0630 (12)0.0618 (11)0.0065 (10)0.0091 (9)0.0085 (9)
C30.0706 (15)0.0630 (12)0.0686 (12)−0.0020 (10)0.0181 (10)0.0123 (9)
C40.0561 (13)0.0752 (14)0.0595 (11)−0.0083 (10)0.0193 (9)−0.0022 (9)
C50.0756 (17)0.0909 (16)0.0801 (13)−0.0151 (13)0.0306 (12)−0.0002 (11)
C60.0581 (16)0.124 (2)0.0903 (16)−0.0246 (14)0.0249 (13)−0.0114 (15)
C70.0544 (14)0.123 (2)0.0797 (14)−0.0008 (13)0.0185 (11)−0.0047 (14)
C80.0516 (12)0.0883 (15)0.0654 (12)0.0054 (11)0.0137 (9)−0.0024 (10)
C90.0517 (12)0.0728 (13)0.0502 (10)0.0031 (9)0.0162 (8)−0.0029 (8)
C100.0531 (11)0.0601 (11)0.0475 (9)0.0074 (9)0.0120 (8)−0.0010 (7)
C110.0616 (13)0.0571 (11)0.0550 (10)0.0116 (9)0.0128 (9)0.0036 (8)
C120.0653 (13)0.0532 (11)0.0628 (10)0.0061 (9)0.0171 (9)0.0013 (8)
C130.0884 (17)0.0583 (13)0.0960 (14)−0.0013 (11)0.0257 (13)0.0075 (11)
C140.0755 (15)0.0725 (14)0.0667 (12)0.0194 (11)0.0181 (10)0.0103 (10)
C150.0481 (11)0.0550 (11)0.0584 (10)−0.0029 (8)0.0078 (8)−0.0001 (8)
C160.0665 (14)0.0746 (13)0.0614 (11)0.0013 (10)0.0213 (10)−0.0024 (9)
C170.0578 (14)0.0732 (14)0.0902 (15)0.0001 (10)0.0288 (11)−0.0033 (10)
C180.0535 (13)0.0555 (12)0.0852 (14)−0.0010 (9)0.0102 (11)0.0016 (10)
C190.0628 (14)0.0818 (14)0.0627 (11)−0.0043 (11)0.0062 (10)0.0005 (10)
C200.0564 (13)0.0825 (14)0.0593 (11)−0.0021 (10)0.0169 (9)0.0014 (9)
C210.0563 (15)0.0937 (18)0.133 (2)0.0003 (12)0.0011 (14)0.0023 (15)

Geometric parameters (Å, °)

N1—C121.374 (2)C10—C111.435 (3)
N1—C11.393 (2)C11—C121.373 (3)
N1—C151.434 (2)C11—C141.421 (3)
N2—C141.143 (2)C12—C131.483 (3)
C1—C101.399 (2)C13—H13A0.9600
C1—C21.400 (2)C13—H13B0.9600
C2—C31.360 (3)C13—H13C0.9600
C2—H20.9300C15—C201.380 (3)
C3—C41.422 (3)C15—C161.382 (3)
C3—H30.9300C16—C171.376 (3)
C4—C51.417 (3)C16—H160.9300
C4—C91.420 (3)C17—C181.378 (3)
C5—C61.377 (3)C17—H170.9300
C5—H50.9300C18—C191.376 (3)
C6—C71.394 (4)C18—C211.509 (3)
C6—H60.9300C19—C201.379 (3)
C7—C81.354 (3)C19—H190.9300
C7—H70.9300C20—H200.9300
C8—C91.409 (3)C21—H21A0.9600
C8—H80.9300C21—H21B0.9600
C9—C101.429 (3)C21—H21C0.9600
C12—N1—C1109.04 (15)C14—C11—C10127.20 (19)
C12—N1—C15125.88 (15)C11—C12—N1108.18 (17)
C1—N1—C15125.07 (14)C11—C12—C13129.44 (18)
N1—C1—C10108.42 (15)N1—C12—C13122.34 (18)
N1—C1—C2128.59 (17)C12—C13—H13A109.5
C10—C1—C2122.97 (17)C12—C13—H13B109.5
C3—C2—C1117.55 (18)H13A—C13—H13B109.5
C3—C2—H2121.2C12—C13—H13C109.5
C1—C2—H2121.2H13A—C13—H13C109.5
C2—C3—C4122.07 (18)H13B—C13—H13C109.5
C2—C3—H3119.0N2—C14—C11179.4 (3)
C4—C3—H3119.0C20—C15—C16119.78 (18)
C5—C4—C9117.6 (2)C20—C15—N1119.91 (18)
C5—C4—C3121.5 (2)C16—C15—N1120.31 (16)
C9—C4—C3120.85 (18)C17—C16—C15119.24 (17)
C6—C5—C4121.0 (2)C17—C16—H16120.4
C6—C5—H5119.5C15—C16—H16120.4
C4—C5—H5119.5C16—C17—C18122.2 (2)
C5—C6—C7120.4 (2)C16—C17—H17118.9
C5—C6—H6119.8C18—C17—H17118.9
C7—C6—H6119.8C19—C18—C17117.41 (19)
C8—C7—C6120.1 (2)C19—C18—C21121.3 (2)
C8—C7—H7120.0C17—C18—C21121.2 (2)
C6—C7—H7120.0C18—C19—C20121.91 (19)
C7—C8—C9121.4 (2)C18—C19—H19119.0
C7—C8—H8119.3C20—C19—H19119.0
C9—C8—H8119.3C19—C20—C15119.5 (2)
C8—C9—C4119.45 (19)C19—C20—H20120.3
C8—C9—C10123.90 (19)C15—C20—H20120.3
C4—C9—C10116.63 (17)C18—C21—H21A109.5
C1—C10—C9119.89 (17)C18—C21—H21B109.4
C1—C10—C11105.56 (17)H21A—C21—H21B109.5
C9—C10—C11134.53 (16)C18—C21—H21C109.4
C12—C11—C14123.93 (19)H21A—C21—H21C109.5
C12—C11—C10108.80 (15)H21B—C21—H21C109.5
C12—N1—C1—C10−0.03 (19)C1—C10—C11—C12−0.5 (2)
C15—N1—C1—C10−178.86 (14)C9—C10—C11—C12−178.67 (19)
C12—N1—C1—C2178.88 (18)C1—C10—C11—C14−177.42 (17)
C15—N1—C1—C20.0 (3)C9—C10—C11—C144.4 (3)
N1—C1—C2—C3−177.95 (18)C14—C11—C12—N1177.53 (16)
C10—C1—C2—C30.8 (3)C10—C11—C12—N10.5 (2)
C1—C2—C3—C4−0.1 (3)C14—C11—C12—C130.0 (3)
C2—C3—C4—C5177.9 (2)C10—C11—C12—C13−177.0 (2)
C2—C3—C4—C9−1.2 (3)C1—N1—C12—C11−0.3 (2)
C9—C4—C5—C6−0.8 (3)C15—N1—C12—C11178.55 (16)
C3—C4—C5—C6−179.95 (19)C1—N1—C12—C13177.43 (18)
C4—C5—C6—C7−0.4 (4)C15—N1—C12—C13−3.8 (3)
C5—C6—C7—C81.2 (4)C12—C11—C14—N2−129 (29)
C6—C7—C8—C9−0.7 (3)C10—C11—C14—N247 (29)
C7—C8—C9—C4−0.6 (3)C12—N1—C15—C20110.1 (2)
C7—C8—C9—C10177.95 (18)C1—N1—C15—C20−71.3 (2)
C5—C4—C9—C81.3 (3)C12—N1—C15—C16−70.1 (2)
C3—C4—C9—C8−179.57 (17)C1—N1—C15—C16108.5 (2)
C5—C4—C9—C10−177.31 (17)C20—C15—C16—C17−0.4 (3)
C3—C4—C9—C101.8 (3)N1—C15—C16—C17179.90 (17)
N1—C1—C10—C9178.82 (15)C15—C16—C17—C18−0.3 (3)
C2—C1—C10—C9−0.2 (3)C16—C17—C18—C191.0 (3)
N1—C1—C10—C110.30 (19)C16—C17—C18—C21−179.8 (2)
C2—C1—C10—C11−178.68 (16)C17—C18—C19—C20−0.9 (3)
C8—C9—C10—C1−179.70 (15)C21—C18—C19—C20179.9 (2)
C4—C9—C10—C1−1.1 (2)C18—C19—C20—C150.3 (3)
C8—C9—C10—C11−1.7 (3)C16—C15—C20—C190.4 (3)
C4—C9—C10—C11176.86 (18)N1—C15—C20—C19−179.86 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16···N2i0.932.603.480 (3)158

Symmetry codes: (i) −x, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5275).

References

  • Du, Y. F., Liu, R. H., Linn, G. & Zhao, K. (2006). Org. Lett.8, 5919–5922. [PubMed]
  • Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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