6-Meth­oxy-2-methyl-1-phenyl-1H-indole-3-carbonitrile

Qiao Yan; Xiuxiang Qi

doi:10.1107/S1600536811038724

. 2011 Sep 30;67(Pt 10):o2798. doi: 10.1107/S1600536811038724

6-Methoxy-2-methyl-1-phenyl-1H-indole-3-carbonitrile

Qiao Yan ^a, Xiuxiang Qi ^a,^*

PMCID: PMC3201306 PMID: 22065016

Abstract

In the title compound, C₁₇H₁₄N₂O, the dihedral angle between the indole ring system and the phenyl ring is 64.48 (7)°. The crystal packing features weak C—H⋯π interactions.

Related literature

For the synthesis of the title compound, see: Du et al. (2006 ▶). For its precursor, see: Jin et al. (2009 ▶). For related structures, see: Yang et al. (2011 ▶); Yan & Qi (2011a ▶,b ▶).

Experimental

Crystal data

C₁₇H₁₄N₂O
M _r = 262.30
Triclinic,
a = 6.3699 (7) Å
b = 10.6084 (10) Å
c = 10.8139 (11) Å
α = 70.059 (10)°
β = 79.455 (13)°
γ = 78.869 (12)°
V = 668.55 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ▶) T _min = 0.981, T _max = 0.984
7078 measured reflections
3157 independent reflections
1404 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.095
S = 0.89
3157 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038724/bt5647sup1.cif

e-67-o2798-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038724/bt5647Isup2.hkl

e-67-o2798-Isup2.hkl^{(154.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811038724/bt5647Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6–C8, C1–C6 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯Cg2ⁱ	0.98	2.78	3.701 (2)	156
C10—H10B⋯Cg3ⁱⁱ	0.98	2.65	3.516 (2)	148
C10—H10C⋯Cg1ⁱⁱⁱ	0.98	2.73	3.509 (2)	137

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

XQ is grateful for financial support of this project by the China Postdoctoral Science Foundation (200904507610).

supplementary crystallographic information

Comment

In our continuous investigation about indole derivatives, herein, we report the title compound (I). In the molecular structure (Fig. 1), the indole ring is almost planar with a dihedral angle of 1.37 (10)° between its pyrrole ring and fused benzene ring, greater than those in 1-(2-chlorophenyl)- 6-fluoro-2-methyl-1H-indole-3-carbonitrile [0.85 (6)°] (Yang et al., 2011) and 1-(4-bromophenyl)-2-methyl-1H-indole-3-carbonitrile [0.95 (16)°] (Yan & Qi, 2011b), but less than that [2.66 (6)°] of our previously reported 1-(4-methoxyphenyl)-2-methyl-1H-indole-3-carbonitrile (Yan & Qi, 2011a).

The indole ring forms an angle of 64.48 (7)° with the phenyl ring, being between those [58.41 (4)° & 58.85 (11) °] reported by our group (Yan & Qi, 2011a,b), and that [80.91 (5)°] reported by Yang et al. (2011).

In the crystal packing, weak C—H···π interaction were observed, establishing the packing (Table 1).

Experimental

The title compound was prepared according to the method of the literature (Du, et al., 2006). Colourless prisms were grown from a mixture of ethyl acetate and petroleum ether.