Crystal structure and Hirshfeld surface analysis of 4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Soukaina El Haddad; Olivier Blacque; Tuncer Hökelek; Ahmed Mazzah; Taha Mohamed Labd; Lhoussaine El Ghayati; Nada Kheira Sebbar

doi:10.1107/S2056989025007686

Crystal structure and Hirshfeld surface analysis of 4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Soukaina El Haddad
, Olivier Blacque
, Tuncer Hökelek
, Ahmed Mazzah
, Taha Mohamed Labd
, Lhoussaine El Ghayati
, Nada Kheira Sebbar

Hacettepe University

Mohammed V University in Rabat
University of Zurich
Science and Technology of Lille USR 3290
Ibn Zohr University

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

Abstract

The molecule of the title compound, C15H13NO2, comprises a non-planar oxazine ring (twisted-boat conformation) fused to a benzene ring, and a benzyl moiety. In the crystal, C-H⋯O hydrogen bonds link the molecules into [010] supramolecular chains, enclosing R22(9) ring motifs. C-H⋯π interactions and very weak π-π stacking between the benzene rings of adjacent molecules help to consolidate the packing. A Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H⋯H (48.8%), H⋯ C/C⋯H (29.3%) and H⋯O/O⋯H (18.9%) interactions.

Original language	English
Pages (from-to)	920-923
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	81
Issue number	Pt 10
DOIs	https://doi.org/10.1107/S2056989025007686
Publication status	Published - 1 Oct 2025

Keywords

1,4-benzoxazin-3-ones
C-H⋯π interaction
crystal structure
heterocycles

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10.1107/S2056989025007686

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title = "Crystal structure and Hirshfeld surface analysis of 4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one",

abstract = "The molecule of the title compound, C15H13NO2, comprises a non-planar oxazine ring (twisted-boat conformation) fused to a benzene ring, and a benzyl moiety. In the crystal, C-H⋯O hydrogen bonds link the molecules into [010] supramolecular chains, enclosing R22(9) ring motifs. C-H⋯π interactions and very weak π-π stacking between the benzene rings of adjacent molecules help to consolidate the packing. A Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H⋯H (48.8\%), H⋯ C/C⋯H (29.3\%) and H⋯O/O⋯H (18.9\%) interactions.",

keywords = "1,4-benzoxazin-3-ones, C-H⋯π interaction, crystal structure, heterocycles",

author = "\{El Haddad\}, Soukaina and Olivier Blacque and Tuncer H{\"o}kelek and Ahmed Mazzah and Labd, \{Taha Mohamed\} and \{El Ghayati\}, Lhoussaine and Sebbar, \{Nada Kheira\}",

year = "2025",

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day = "1",

doi = "10.1107/S2056989025007686",

language = "English",

volume = "81",

pages = "920--923",

journal = "Acta Crystallographica Section E: Crystallographic Communications",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "Pt 10",

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TY - JOUR

T1 - Crystal structure and Hirshfeld surface analysis of 4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one

AU - El Haddad, Soukaina

AU - Blacque, Olivier

AU - Hökelek, Tuncer

AU - Mazzah, Ahmed

AU - Labd, Taha Mohamed

AU - El Ghayati, Lhoussaine

AU - Sebbar, Nada Kheira

PY - 2025/10/1

Y1 - 2025/10/1

N2 - The molecule of the title compound, C15H13NO2, comprises a non-planar oxazine ring (twisted-boat conformation) fused to a benzene ring, and a benzyl moiety. In the crystal, C-H⋯O hydrogen bonds link the molecules into [010] supramolecular chains, enclosing R22(9) ring motifs. C-H⋯π interactions and very weak π-π stacking between the benzene rings of adjacent molecules help to consolidate the packing. A Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H⋯H (48.8%), H⋯ C/C⋯H (29.3%) and H⋯O/O⋯H (18.9%) interactions.

AB - The molecule of the title compound, C15H13NO2, comprises a non-planar oxazine ring (twisted-boat conformation) fused to a benzene ring, and a benzyl moiety. In the crystal, C-H⋯O hydrogen bonds link the molecules into [010] supramolecular chains, enclosing R22(9) ring motifs. C-H⋯π interactions and very weak π-π stacking between the benzene rings of adjacent molecules help to consolidate the packing. A Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H⋯H (48.8%), H⋯ C/C⋯H (29.3%) and H⋯O/O⋯H (18.9%) interactions.

KW - 1,4-benzoxazin-3-ones

KW - C-H⋯π interaction

KW - crystal structure

KW - heterocycles

UR - https://www.scopus.com/pages/publications/105020692671

U2 - 10.1107/S2056989025007686

DO - 10.1107/S2056989025007686

M3 - Article

C2 - 41059316

AN - SCOPUS:105020692671

SN - 2056-9890

VL - 81

SP - 920

EP - 923

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

IS - Pt 10

ER -

Crystal structure and Hirshfeld surface analysis of 4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Abstract

Keywords

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