The crystal structure of (RS)-7-chloro-2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one: two hydrogen bonds generate an elegant three-dimensional framework structure

Kereyagalahally H. Narasimhamurthy; Chandra .; Belakavadi K. Sagar; Kanchugarakoppal S. Rangappa; Hemmige S. Yathirajan; Christopher Glidewell

doi:10.1107/S2056989019007023

The crystal structure of (RS)-7-chloro-2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one: two hydrogen bonds generate an elegant three-dimensional framework structure

Kereyagalahally H. Narasimhamurthy, Chandra ., Belakavadi K. Sagar, Kanchugarakoppal S. Rangappa, Hemmige S. Yathirajan, Christopher Glidewell

School of Chemistry

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Abstract

In the title compound, C₆₁H₁₅ClN₂O₃, the heterocyclic ring adopts an envelope conformation, folded across the N⋯N line, with the 2,5-dimethoxyphenyl unit occupying a quasi-axial site. There are two N—H⋯O hydrogen bonds in the structure: one hydrogen bond links molecules related by a 4₁ screw axis to form a C(6) chain, and the other links inversion-related pairs of molecules to form an R₂²(8) ring. The ring motif links all of the chains into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds.

Original language	English
Pages (from-to)	843-847
Number of pages	5
Journal	Acta Crystallographica Section E
Volume	75
Issue number	6
Early online date	21 May 2019
DOIs	https://doi.org/10.1107/S2056989019007023
Publication status	Published - Jun 2019

Keywords

Heterocyclic compounds
Reduced quinazolinones
Crystal structure
Molecular conformation
Hydrogen bonding
Supramolecular assembly

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Copyright © 2019 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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Narasimhamurthy, K. H., ., C., Sagar, B. K., Rangappa, K. S., Yathirajan, H. S., & Glidewell, C. (2019). The crystal structure of (RS)-7-chloro-2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one: two hydrogen bonds generate an elegant three-dimensional framework structure. Acta Crystallographica Section E, 75(6), 843-847. https://doi.org/10.1107/S2056989019007023

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title = "The crystal structure of (RS)-7-chloro-2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one: two hydrogen bonds generate an elegant three-dimensional framework structure",

abstract = "In the title compound, C61H15ClN2O3, the heterocyclic ring adopts an envelope conformation, folded across the N⋯N line, with the 2,5-dimethoxyphenyl unit occupying a quasi-axial site. There are two N—H⋯O hydrogen bonds in the structure: one hydrogen bond links molecules related by a 41 screw axis to form a C(6) chain, and the other links inversion-related pairs of molecules to form an R22(8) ring. The ring motif links all of the chains into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds.",

keywords = "Heterocyclic compounds, Reduced quinazolinones, Crystal structure, Molecular conformation, Hydrogen bonding, Supramolecular assembly",

author = "Narasimhamurthy, \{Kereyagalahally H.\} and Chandra . and Sagar, \{Belakavadi K.\} and Rangappa, \{Kanchugarakoppal S.\} and Yathirajan, \{Hemmige S.\} and Christopher Glidewell",

note = "KHN is grateful to UGC, RFSMS, Government of India for a Research Fellowship. BKS thanks the University of Mysore, for research facilities.",

year = "2019",

month = jun,

doi = "10.1107/S2056989019007023",

language = "English",

volume = "75",

pages = "843--847",

journal = "Acta Crystallographica Section E",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "6",

}

The crystal structure of (RS)-7-chloro-2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one: two hydrogen bonds generate an elegant three-dimensional framework structure. / Narasimhamurthy, Kereyagalahally H.; ., Chandra; Sagar, Belakavadi K. et al.
In: Acta Crystallographica Section E, Vol. 75, No. 6, 06.2019, p. 843-847.

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

TY - JOUR

T1 - The crystal structure of (RS)-7-chloro-2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one

T2 - two hydrogen bonds generate an elegant three-dimensional framework structure

AU - Narasimhamurthy, Kereyagalahally H.

AU - ., Chandra

AU - Sagar, Belakavadi K.

AU - Rangappa, Kanchugarakoppal S.

AU - Yathirajan, Hemmige S.

AU - Glidewell, Christopher

N1 - KHN is grateful to UGC, RFSMS, Government of India for a Research Fellowship. BKS thanks the University of Mysore, for research facilities.

PY - 2019/6

Y1 - 2019/6

N2 - In the title compound, C61H15ClN2O3, the heterocyclic ring adopts an envelope conformation, folded across the N⋯N line, with the 2,5-dimethoxyphenyl unit occupying a quasi-axial site. There are two N—H⋯O hydrogen bonds in the structure: one hydrogen bond links molecules related by a 41 screw axis to form a C(6) chain, and the other links inversion-related pairs of molecules to form an R22(8) ring. The ring motif links all of the chains into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds.

AB - In the title compound, C61H15ClN2O3, the heterocyclic ring adopts an envelope conformation, folded across the N⋯N line, with the 2,5-dimethoxyphenyl unit occupying a quasi-axial site. There are two N—H⋯O hydrogen bonds in the structure: one hydrogen bond links molecules related by a 41 screw axis to form a C(6) chain, and the other links inversion-related pairs of molecules to form an R22(8) ring. The ring motif links all of the chains into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds.

KW - Heterocyclic compounds

KW - Reduced quinazolinones

KW - Crystal structure

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

UR - https://www.scopus.com/pages/publications/85069825584

U2 - 10.1107/S2056989019007023

DO - 10.1107/S2056989019007023

M3 - Article

SN - 2056-9890

VL - 75

SP - 843

EP - 847

JO - Acta Crystallographica Section E

JF - Acta Crystallographica Section E

IS - 6

ER -

The crystal structure of (RS)-7-chloro-2-(2,5-dimethoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one: two hydrogen bonds generate an elegant three-dimensional framework structure

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