Rac-(Z)-Methyl 1-benzyl-3-[(3-hydroxyquinuclidin-2-ylidene)methyl]-1H- indole-6-carboxylate

Narsimha Reddy Penthala; Purushotham Rao Ponugoti; Sean Parkin; Peter A. Crooks

doi:10.1107/S1600536812040731

Rac-(Z)-Methyl 1-benzyl-3-[(3-hydroxyquinuclidin-2-ylidene)methyl]-1H- indole-6-carboxylate

Narsimha Reddy Penthala, Purushotham Rao Ponugoti, Sean Parkin, Peter A. Crooks

Chemistry

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

1 Scopus citations

Abstract

In the title compound, C₂5H₂6N₂O ₃, the double bond connecting the aza-bicyclic and indole units has Z geometry. The compound was obtained as a racemate, and since the crystal is centrosymmetric it contains equal amounts of the S and R enantiomers. However, the structure is disordered such that the asymmetric unit contains both enantiomers in unequal amounts [refined occupancies 0.904(2) and 0.096(2)]. The dihedral angle between the benzene ring of the benzyl group and the mean plane of the indole ring is 76.07(3)°. In the crystal, molecules are linked by O-H⋯Ocarbonyl hydrogen bonds into chains propagating in [110].

Original language	English
Pages (from-to)	o3111
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	68
Issue number	11
DOIs	https://doi.org/10.1107/S1600536812040731
State	Published - Nov 2012

Keywords

R factor = 0.039
T = 90 K
data-to-parameter ratio = 14.7
disorder in main residue
mean ̄(C-C) = 0.002 Å
single-crystal X-ray study
wR factor = 0.102

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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@article{31881c485cde474aadcbc15f841411ef,

title = "Rac-(Z)-Methyl 1-benzyl-3-[(3-hydroxyquinuclidin-2-ylidene)methyl]-1H- indole-6-carboxylate",

abstract = "In the title compound, C25H26N2O 3, the double bond connecting the aza-bicyclic and indole units has Z geometry. The compound was obtained as a racemate, and since the crystal is centrosymmetric it contains equal amounts of the S and R enantiomers. However, the structure is disordered such that the asymmetric unit contains both enantiomers in unequal amounts [refined occupancies 0.904(2) and 0.096(2)]. The dihedral angle between the benzene ring of the benzyl group and the mean plane of the indole ring is 76.07(3)°. In the crystal, molecules are linked by O-H⋯Ocarbonyl hydrogen bonds into chains propagating in [110].",

keywords = "R factor = 0.039, T = 90 K, data-to-parameter ratio = 14.7, disorder in main residue, mean{\= }(C-C) = 0.002 {\AA}, single-crystal X-ray study, wR factor = 0.102",

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

year = "2012",

month = nov,

doi = "10.1107/S1600536812040731",

language = "English",

volume = "68",

pages = "o3111",

number = "11",

}

TY - JOUR

T1 - Rac-(Z)-Methyl 1-benzyl-3-[(3-hydroxyquinuclidin-2-ylidene)methyl]-1H- indole-6-carboxylate

AU - Penthala, Narsimha Reddy

AU - Ponugoti, Purushotham Rao

AU - Parkin, Sean

AU - Crooks, Peter A.

PY - 2012/11

Y1 - 2012/11

N2 - In the title compound, C25H26N2O 3, the double bond connecting the aza-bicyclic and indole units has Z geometry. The compound was obtained as a racemate, and since the crystal is centrosymmetric it contains equal amounts of the S and R enantiomers. However, the structure is disordered such that the asymmetric unit contains both enantiomers in unequal amounts [refined occupancies 0.904(2) and 0.096(2)]. The dihedral angle between the benzene ring of the benzyl group and the mean plane of the indole ring is 76.07(3)°. In the crystal, molecules are linked by O-H⋯Ocarbonyl hydrogen bonds into chains propagating in [110].

AB - In the title compound, C25H26N2O 3, the double bond connecting the aza-bicyclic and indole units has Z geometry. The compound was obtained as a racemate, and since the crystal is centrosymmetric it contains equal amounts of the S and R enantiomers. However, the structure is disordered such that the asymmetric unit contains both enantiomers in unequal amounts [refined occupancies 0.904(2) and 0.096(2)]. The dihedral angle between the benzene ring of the benzyl group and the mean plane of the indole ring is 76.07(3)°. In the crystal, molecules are linked by O-H⋯Ocarbonyl hydrogen bonds into chains propagating in [110].

KW - R factor = 0.039

KW - T = 90 K

KW - data-to-parameter ratio = 14.7

KW - disorder in main residue

KW - mean ̄(C-C) = 0.002 Å

KW - single-crystal X-ray study

KW - wR factor = 0.102

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UR - http://www.scopus.com/inward/citedby.url?scp=84870943392&partnerID=8YFLogxK

U2 - 10.1107/S1600536812040731

DO - 10.1107/S1600536812040731

M3 - Article

C2 - 23284437

AN - SCOPUS:84870943392

SN - 1600-5368

VL - 68

SP - o3111

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 11

ER -

Rac-(Z)-Methyl 1-benzyl-3-[(3-hydroxyquinuclidin-2-ylidene)methyl]-1H- indole-6-carboxylate

Abstract

Keywords

ASJC Scopus subject areas

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