Crystal structure of 2-[4-(4-chlorophen-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1, 3-dione dimethyl sulfoxide monosolvate

Ísmail Çelik; Mehmet Akkurt; Aliasghar Jarrahpour; Javad Ameri Rad; Ömer Çelik; W. T A Harrison

doi:10.1107/S2056989015001425

Crystal structure of 2-[4-(4-chlorophen-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1, 3-dione dimethyl sulfoxide monosolvate

Ísmail Çelik
, Mehmet Akkurt^*
, Aliasghar Jarrahpour
, Javad Ameri Rad
, Ömer Çelik
, W. T A Harrison (Editor)

^*Corresponding author for this work

Chemistry

Cumhuriyet University
Erciyes University
Shiraz University
Dicle University

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

5 Citations (Scopus)

12 Downloads (Pure)

Abstract

In the title solvated compound, C₂₈H₁₉N₂O₄C₂H₆OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1, 3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C - H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C - H⋯O hydrogen bonds, C - H⋯π=i interactions and aromatic π-π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

Original language	English
Pages (from-to)	o129-o130
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	2
Early online date	28 Jan 2015
DOIs	https://doi.org/10.1107/S2056989015001425
Publication status	Published - 1 Feb 2015

Bibliographical note

Acknowledgements
The authors are indebted to the X-ray laboratory of Dicle University Scientiﬁc and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. AJ and JAR thank the Shiraz University Research Council for ﬁnancial support (grant No. 93-GR–SC-23).

Keywords

1 H-benzo[de]isoquinoline-1,3(2H)-dione group
Azetidin-2-ones
Crystal structure
Disorder
-lactam ring

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Crystal structure of 2-[4-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-oxoazetidin3-yl]benzo[de]isoquinoline-1,3-dione dimethyl sulfoxide monosolvat
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Crystal structure of 2-[4-(4-chlorophen-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1, 3-dione dimethyl sulfoxide monosolvate. / Çelik, Ísmail; Akkurt, Mehmet; Jarrahpour, Aliasghar et al.
In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 2, 01.02.2015, p. o129-o130.

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

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title = "Crystal structure of 2-[4-(4-chlorophen-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1, 3-dione dimethyl sulfoxide monosolvate",

abstract = "In the title solvated compound, C28H19N2O4C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 {\AA}). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1, 3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C - H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C - H⋯O hydrogen bonds, C - H⋯π=i interactions and aromatic π-π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) {\AA}], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.",

keywords = "1 H-benzo[de]isoquinoline-1,3(2H)-dione group, Azetidin-2-ones, Crystal structure, Disorder, -lactam ring",

author = "{\'I}smail {\c C}elik and Mehmet Akkurt and Aliasghar Jarrahpour and Rad, \{Javad Ameri\} and {\"O}mer {\c C}elik and Harrison, \{W. T A\}",

note = "Acknowledgements The authors are indebted to the X-ray laboratory of Dicle University Scientiﬁc and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. AJ and JAR thank the Shiraz University Research Council for ﬁnancial support (grant No. 93-GR{\textendash}SC-23).",

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AU - Çelik, Ísmail

AU - Akkurt, Mehmet

AU - Jarrahpour, Aliasghar

AU - Rad, Javad Ameri

AU - Çelik, Ömer

A2 - Harrison, W. T A

N1 - Acknowledgements The authors are indebted to the X-ray laboratory of Dicle University Scientiﬁc and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. AJ and JAR thank the Shiraz University Research Council for ﬁnancial support (grant No. 93-GR–SC-23).

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N2 - In the title solvated compound, C28H19N2O4C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1, 3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C - H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C - H⋯O hydrogen bonds, C - H⋯π=i interactions and aromatic π-π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

AB - In the title solvated compound, C28H19N2O4C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1, 3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C - H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C - H⋯O hydrogen bonds, C - H⋯π=i interactions and aromatic π-π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

KW - 1 H-benzo[de]isoquinoline-1,3(2H)-dione group

KW - Azetidin-2-ones

KW - Crystal structure

KW - Disorder

KW - -lactam ring

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JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

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ER -

Crystal structure of 2-[4-(4-chlorophen-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1, 3-dione dimethyl sulfoxide monosolvate

Abstract

Bibliographical note

Keywords

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