2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene) -2-cyanoacetamide

Madeleine Helliwell; Mehdi M. Baradarani; Maryam Alyari; Arash Afghan; John A. Joule

doi:10.1107/S1600536811053918

2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene) -2-cyanoacetamide

Madeleine Helliwell, Mehdi M. Baradarani^*, Maryam Alyari, Arash Afghan, John A. Joule

^*Corresponding author for this work

University of Urmia

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

Abstract

Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1 H-indol-2-ylidene) propanedial with hydroxylamine gives the title compound, C ₁₄H ₁₄ClN ₃O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyanoacrylamide unit. The orientation of the acetamide group arises from intramolecular hydrogen bonding between the indole N-H and carbonyl groups. In the crystal, inversion-related acetamide groups form N-H ·· · O hydrogen-bonded dimers in graph-set R ₂ ²(8) motifs, whilst dimers are also formed by pairs of aminenitrile N-H ··· N hydrogen bonds in R ² ₂(12) motifs. These interactions together generate ribbons that propagate along the b-axis direction.

Original language	English
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	68
Issue number	1
DOIs	https://doi.org/10.1107/S1600536811053918
Publication status	Published - 1 Jan 2012

Keywords

Data-to-parameter ratio = 12.8
Mean σ(C-C) = 0.006 Å
R factor = 0.065
Single-crystal X-ray study
T = 100 K
wR factor = 0.132

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10.1107/S1600536811053918

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title = "2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene) -2-cyanoacetamide",

abstract = "Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1 H-indol-2-ylidene) propanedial with hydroxylamine gives the title compound, C 14H 14ClN 3O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyanoacrylamide unit. The orientation of the acetamide group arises from intramolecular hydrogen bonding between the indole N-H and carbonyl groups. In the crystal, inversion-related acetamide groups form N-H ·· · O hydrogen-bonded dimers in graph-set R 2 2(8) motifs, whilst dimers are also formed by pairs of aminenitrile N-H ··· N hydrogen bonds in R 2 2(12) motifs. These interactions together generate ribbons that propagate along the b-axis direction.",

keywords = "Data-to-parameter ratio = 12.8, Mean σ(C-C) = 0.006 {\AA}, R factor = 0.065, Single-crystal X-ray study, T = 100 K, wR factor = 0.132",

author = "Madeleine Helliwell and Baradarani, {Mehdi M.} and Maryam Alyari and Arash Afghan and Joule, {John A.}",

year = "2012",

month = jan,

day = "1",

doi = "10.1107/S1600536811053918",

language = "English",

volume = "68",

journal = "Acta Crystallographica Section E: Structure Reports Online",

issn = "1600-5368",

publisher = "International Union of Crystallography",

number = "1",

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TY - JOUR

T1 - 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene) -2-cyanoacetamide

AU - Helliwell, Madeleine

AU - Baradarani, Mehdi M.

AU - Alyari, Maryam

AU - Afghan, Arash

AU - Joule, John A.

PY - 2012/1/1

Y1 - 2012/1/1

N2 - Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1 H-indol-2-ylidene) propanedial with hydroxylamine gives the title compound, C 14H 14ClN 3O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyanoacrylamide unit. The orientation of the acetamide group arises from intramolecular hydrogen bonding between the indole N-H and carbonyl groups. In the crystal, inversion-related acetamide groups form N-H ·· · O hydrogen-bonded dimers in graph-set R 2 2(8) motifs, whilst dimers are also formed by pairs of aminenitrile N-H ··· N hydrogen bonds in R 2 2(12) motifs. These interactions together generate ribbons that propagate along the b-axis direction.

AB - Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1 H-indol-2-ylidene) propanedial with hydroxylamine gives the title compound, C 14H 14ClN 3O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyanoacrylamide unit. The orientation of the acetamide group arises from intramolecular hydrogen bonding between the indole N-H and carbonyl groups. In the crystal, inversion-related acetamide groups form N-H ·· · O hydrogen-bonded dimers in graph-set R 2 2(8) motifs, whilst dimers are also formed by pairs of aminenitrile N-H ··· N hydrogen bonds in R 2 2(12) motifs. These interactions together generate ribbons that propagate along the b-axis direction.

KW - Data-to-parameter ratio = 12.8

KW - Mean σ(C-C) = 0.006 Å

KW - R factor = 0.065

KW - Single-crystal X-ray study

KW - T = 100 K

KW - wR factor = 0.132

UR - http://www.scopus.com/inward/record.url?scp=84855401568&partnerID=8YFLogxK

U2 - 10.1107/S1600536811053918

DO - 10.1107/S1600536811053918

M3 - Article

AN - SCOPUS:84855401568

SN - 1600-5368

VL - 68

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 1

ER -

2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene) -2-cyanoacetamide

Abstract

Keywords

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CCDC 861908: Experimental Crystal Structure Determination

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2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene) -2-cyanoacetamide

Abstract

Keywords

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Datasets

CCDC 861908: Experimental Crystal Structure Determination

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