(Z)-3-(1H-Indol-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile

Narsimha Reddy Penthala; Sean Parkin; Peter A. Crooks

doi:10.1107/S1600536812005855

(Z)-3-(1H-Indol-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile

Narsimha Reddy Penthala, Sean Parkin, Peter A. Crooks

Chemistry

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

In the title compound, C ₂₀H ₁₈N ₂O ₃, the C=C bond of the acrylonitrile group that links the indole and the 3,4,5-trimeth-oxy-phenyl rings has Z geometry, with dihedral angles between the plane of the acrylonitrile unit and the planes of the benzene and indole ring systems of 21.96 (5) and 38.94 (7)°, respectively. The acrylonitrile group is planar (r.m.s. deviation from planarity = 0.037 Å). molecules are linked into head-to-tail chains that propagate along the b-axis direction by bifurcated N - H⋯O intermolecular hydrogen bonds, which form an R ₁ ²(5) motif between the indole NH group and the two methoxy O atoms furthest from the nitrile group.

Original language	English
Pages (from-to)	o729
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	68
Issue number	3
DOIs	https://doi.org/10.1107/S1600536812005855
State	Published - Mar 2012

Keywords

R factor =0.037
T = 90 K
data-to-parameter ratio = 12.8
mean σ(C-C) = 0.002 Å
single-crystal X-ray study
wR factor = 0.097

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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@article{6b25394dcc6d4ae0b62510414f6e4652,

title = "(Z)-3-(1H-Indol-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile",

abstract = "In the title compound, C 20H 18N 2O 3, the C=C bond of the acrylonitrile group that links the indole and the 3,4,5-trimeth-oxy-phenyl rings has Z geometry, with dihedral angles between the plane of the acrylonitrile unit and the planes of the benzene and indole ring systems of 21.96 (5) and 38.94 (7)°, respectively. The acrylonitrile group is planar (r.m.s. deviation from planarity = 0.037 {\AA}). molecules are linked into head-to-tail chains that propagate along the b-axis direction by bifurcated N - H⋯O intermolecular hydrogen bonds, which form an R 1 2(5) motif between the indole NH group and the two methoxy O atoms furthest from the nitrile group.",

keywords = "R factor =0.037, T = 90 K, data-to-parameter ratio = 12.8, mean σ(C-C) = 0.002 {\AA}, single-crystal X-ray study, wR factor = 0.097",

author = "Penthala, {Narsimha Reddy} and Sean Parkin and Crooks, {Peter A.}",

year = "2012",

month = mar,

doi = "10.1107/S1600536812005855",

language = "English",

volume = "68",

pages = "o729",

number = "3",

}

TY - JOUR

T1 - (Z)-3-(1H-Indol-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile

AU - Penthala, Narsimha Reddy

AU - Parkin, Sean

AU - Crooks, Peter A.

PY - 2012/3

Y1 - 2012/3

N2 - In the title compound, C 20H 18N 2O 3, the C=C bond of the acrylonitrile group that links the indole and the 3,4,5-trimeth-oxy-phenyl rings has Z geometry, with dihedral angles between the plane of the acrylonitrile unit and the planes of the benzene and indole ring systems of 21.96 (5) and 38.94 (7)°, respectively. The acrylonitrile group is planar (r.m.s. deviation from planarity = 0.037 Å). molecules are linked into head-to-tail chains that propagate along the b-axis direction by bifurcated N - H⋯O intermolecular hydrogen bonds, which form an R 1 2(5) motif between the indole NH group and the two methoxy O atoms furthest from the nitrile group.

AB - In the title compound, C 20H 18N 2O 3, the C=C bond of the acrylonitrile group that links the indole and the 3,4,5-trimeth-oxy-phenyl rings has Z geometry, with dihedral angles between the plane of the acrylonitrile unit and the planes of the benzene and indole ring systems of 21.96 (5) and 38.94 (7)°, respectively. The acrylonitrile group is planar (r.m.s. deviation from planarity = 0.037 Å). molecules are linked into head-to-tail chains that propagate along the b-axis direction by bifurcated N - H⋯O intermolecular hydrogen bonds, which form an R 1 2(5) motif between the indole NH group and the two methoxy O atoms furthest from the nitrile group.

KW - R factor =0.037

KW - T = 90 K

KW - data-to-parameter ratio = 12.8

KW - mean σ(C-C) = 0.002 Å

KW - single-crystal X-ray study

KW - wR factor = 0.097

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UR - http://www.scopus.com/inward/citedby.url?scp=84857930145&partnerID=8YFLogxK

U2 - 10.1107/S1600536812005855

DO - 10.1107/S1600536812005855

M3 - Article

C2 - 22412611

AN - SCOPUS:84857930145

SN - 1600-5368

VL - 68

SP - o729

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 3

ER -

(Z)-3-(1H-Indol-3-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile

Abstract

Keywords

ASJC Scopus subject areas

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