Different patterns of supra­molecular aggregation in three amides containing N-(benzo[d]thia­zol­yl) substituents

Ninganayaka Mahesha; Hemmige S. Yathirajan; Holalagudu A. Nagma Banu; Balakrishna Kalluraya; Sabine Foro; Christopher Glidewell

doi:10.1107/S2056989021003637

Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents

Ninganayaka Mahesha, Hemmige S. Yathirajan, Holalagudu A. Nagma Banu, Balakrishna Kalluraya, Sabine Foro, Christopher Glidewell

School of Chemistry

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

Abstract

Crystal structures are reported for three amides containing N-benzo[d]thiazole substituents. In N-(benzo[d]thiazol-6-yl)-3-bromobenzamide, C₁₄H₉BrN₂OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the molecules are linked by N—H⋯O and C—H⋯N hydrogen bonds to form ribbons of R³₃(19) rings, which are linked into sheets by short Br⋯Br interactions [3.5812 (6) Å]. N-(6-Methoxybenzo[d]thiazol-2-yl)-2-nitrobenzamide, C₁₅H₁₁N₃O₄S, crystallizes with Z′ = 2 in space group Pna2₁: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent molecules and a combination of two N—H⋯N and five C—H⋯O hydrogen bonds links the molecules into a three-dimensional network. The molecules of 5-cyclopropyl-N-(6-methoxybenzo[d]thiazol-2-yl)isoxazole-3-carboxamide, C₁₅H₁₃N₃O₃S, exhibit two forms of disorder, in the methoxy group and in the cyclopropylisoxazole unit; symmetry-related pairs of molecules are linked into dimers by pairwise N—H⋯N hydrogen bonds. Comparisons are made with the structures of some related compounds.

Original language	English
Pages (from-to)	504-511
Number of pages	8
Journal	Acta Crystallographica Section E Crystallographic Communications
Volume	77
Issue number	Part 5
Early online date	9 Apr 2021
DOIs	https://doi.org/10.1107/S2056989021003637
Publication status	Published - May 2021

Keywords

Benzo[d]thiazoles
Crystal structure
Disorder
Halogen bonding
Heterocyclic compounds
Hydrogen bonding
Molecular conformation

Access to Document

10.1107/S2056989021003637Licence: CC BY

Mahesha_2021_Acta-Cryst-E_Different-patterns
Copyright © 2020 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.
Final published version, 1.61 MBLicence: CC BY

Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents (dataset)
Mahesha, N. (Creator), Yathirajan, H. S. (Creator), Nagma Banu, H. A. (Creator), Kalluraya, B. (Creator), Foro, S. (Creator) & Glidewell, C. (Creator), Cambridge Crystallographic Data Centre, 4 Apr 2021
DOI: 10.5517/ccdc.csd.cc27nh7n, https://dx.doi.org/10.5517/ccdc.csd.cc27nh6m and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc27nh5l (show fewer)
Dataset

Cite this

@article{aa37d4ca32574657a7c33064ae59921e,

title = "Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents",

abstract = "Crystal structures are reported for three amides containing N-benzo[d]thiazole substituents. In N-(benzo[d]thiazol-6-yl)-3-bromobenzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the molecules are linked by N—H⋯O and C—H⋯N hydrogen bonds to form ribbons of R33(19) rings, which are linked into sheets by short Br⋯Br interactions [3.5812 (6) {\AA}]. N-(6-Methoxybenzo[d]thiazol-2-yl)-2-nitrobenzamide, C15H11N3O4S, crystallizes with Z′ = 2 in space group Pna21: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent molecules and a combination of two N—H⋯N and five C—H⋯O hydrogen bonds links the molecules into a three-dimensional network. The molecules of 5-cyclopropyl-N-(6-methoxybenzo[d]thiazol-2-yl)isoxazole-3-carboxamide, C15H13N3O3S, exhibit two forms of disorder, in the methoxy group and in the cyclopropylisoxazole unit; symmetry-related pairs of molecules are linked into dimers by pairwise N—H⋯N hydrogen bonds. Comparisons are made with the structures of some related compounds.",

keywords = "Benzo[d]thiazoles, Crystal structure, Disorder, Halogen bonding, Heterocyclic compounds, Hydrogen bonding, Molecular conformation",

author = "Ninganayaka Mahesha and Yathirajan, {Hemmige S.} and {Nagma Banu}, {Holalagudu A.} and Balakrishna Kalluraya and Sabine Foro and Christopher Glidewell",

note = "HSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.",

year = "2021",

month = may,

doi = "10.1107/S2056989021003637",

language = "English",

volume = "77",

pages = "504--511",

journal = "Acta Crystallographica Section E Crystallographic Communications",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "Part 5",

}

Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents. / Mahesha, Ninganayaka; Yathirajan, Hemmige S.; Nagma Banu, Holalagudu A. et al.
In: Acta Crystallographica Section E Crystallographic Communications, Vol. 77, No. Part 5, 05.2021, p. 504-511.

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

TY - JOUR

T1 - Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents

AU - Mahesha, Ninganayaka

AU - Yathirajan, Hemmige S.

AU - Nagma Banu, Holalagudu A.

AU - Kalluraya, Balakrishna

AU - Foro, Sabine

AU - Glidewell, Christopher

N1 - HSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.

PY - 2021/5

Y1 - 2021/5

N2 - Crystal structures are reported for three amides containing N-benzo[d]thiazole substituents. In N-(benzo[d]thiazol-6-yl)-3-bromobenzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the molecules are linked by N—H⋯O and C—H⋯N hydrogen bonds to form ribbons of R33(19) rings, which are linked into sheets by short Br⋯Br interactions [3.5812 (6) Å]. N-(6-Methoxybenzo[d]thiazol-2-yl)-2-nitrobenzamide, C15H11N3O4S, crystallizes with Z′ = 2 in space group Pna21: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent molecules and a combination of two N—H⋯N and five C—H⋯O hydrogen bonds links the molecules into a three-dimensional network. The molecules of 5-cyclopropyl-N-(6-methoxybenzo[d]thiazol-2-yl)isoxazole-3-carboxamide, C15H13N3O3S, exhibit two forms of disorder, in the methoxy group and in the cyclopropylisoxazole unit; symmetry-related pairs of molecules are linked into dimers by pairwise N—H⋯N hydrogen bonds. Comparisons are made with the structures of some related compounds.

AB - Crystal structures are reported for three amides containing N-benzo[d]thiazole substituents. In N-(benzo[d]thiazol-6-yl)-3-bromobenzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the molecules are linked by N—H⋯O and C—H⋯N hydrogen bonds to form ribbons of R33(19) rings, which are linked into sheets by short Br⋯Br interactions [3.5812 (6) Å]. N-(6-Methoxybenzo[d]thiazol-2-yl)-2-nitrobenzamide, C15H11N3O4S, crystallizes with Z′ = 2 in space group Pna21: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent molecules and a combination of two N—H⋯N and five C—H⋯O hydrogen bonds links the molecules into a three-dimensional network. The molecules of 5-cyclopropyl-N-(6-methoxybenzo[d]thiazol-2-yl)isoxazole-3-carboxamide, C15H13N3O3S, exhibit two forms of disorder, in the methoxy group and in the cyclopropylisoxazole unit; symmetry-related pairs of molecules are linked into dimers by pairwise N—H⋯N hydrogen bonds. Comparisons are made with the structures of some related compounds.

KW - Benzo[d]thiazoles

KW - Crystal structure

KW - Disorder

KW - Halogen bonding

KW - Heterocyclic compounds

KW - Hydrogen bonding

KW - Molecular conformation

U2 - 10.1107/S2056989021003637

DO - 10.1107/S2056989021003637

M3 - Article

SN - 2056-9890

VL - 77

SP - 504

EP - 511

JO - Acta Crystallographica Section E Crystallographic Communications

JF - Acta Crystallographica Section E Crystallographic Communications

IS - Part 5

ER -

Different patterns of supra­molecular aggregation in three amides containing N-(benzo[d]thia­zol­yl) substituents

Abstract

Keywords

Access to Document

Fingerprint

Datasets

Different patterns of supra­molecular aggregation in three amides containing N-(benzo[d]thia­zol­yl) substituents (dataset)

Cite this

Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents

Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents (dataset)