N-(4-Amino-1,2,5-oxadiazol-3-yl)formamide

Firudin I. Guseinov; Tuncer Hökelek; Elena V. Shuvalova; Aida I. Samigullina; Nizami A. Ekberov; Khudayar I. Hasanov; Mohammed Hadi Al-Douh

doi:10.1107/S2414314625007205

N-(4-Amino-1,2,5-oxadiazol-3-yl)formamide

Firudin I. Guseinov
, Tuncer Hökelek
, Elena V. Shuvalova
, Aida I. Samigullina
, Nizami A. Ekberov
, Khudayar I. Hasanov
, Mohammed Hadi Al-Douh

Hacettepe University

Moscow State University of Design and Technology
Russian Academy of Sciences
Azerbaijan State Pedagogical University
Azerbaycan Tibb Universiteti
Hadhramout University of Science and Technology

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

Abstract

The asymmetric unit of the title compound, C₃H₄N₄O₂, contains two coplanar molecules (A and B) completely located on mirror planes. In the crystal, N—H· · ·O, N—H· · ·N, C—H· · ·O and C—H· · ·N hydrogen bonds link the molecules into sheets parallel to (010). There are neither significant π–π nor C—H· · ·π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packings of molecules A and B are from H· · ·O/O· · ·H (32.4% for A, 30.1% for B), H· · ·N/N· · ·H (28.2%, 31.5%) and H· · ·H (12.3%, 8.0%) interactions.

Original language	English
Article number	x250720
Pages (from-to)	x250720
Journal	IUCrData
Volume	10
Issue number	Pt 8
DOIs	https://doi.org/10.1107/S2414314625007205
Publication status	Published - 1 Aug 2025

Keywords

2,2-dihalo-3-oxoaldehydes
crystal structure
non-covalent interactions
pyrazol

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10.1107/S2414314625007205

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@article{8241b98bd5544a05864faa6c0a8e7ae1,

title = "N-(4-Amino-1,2,5-oxadiazol-3-yl)formamide",

abstract = "The asymmetric unit of the title compound, C3H4N4O2, contains two coplanar molecules (A and B) completely located on mirror planes. In the crystal, N—H· · ·O, N—H· · ·N, C—H· · ·O and C—H· · ·N hydrogen bonds link the molecules into sheets parallel to (010). There are neither significant π–π nor C—H· · ·π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packings of molecules A and B are from H· · ·O/O· · ·H (32.4\% for A, 30.1\% for B), H· · ·N/N· · ·H (28.2\%, 31.5\%) and H· · ·H (12.3\%, 8.0\%) interactions.",

keywords = "2,2-dihalo-3-oxoaldehydes, crystal structure, non-covalent interactions, pyrazol",

author = "Guseinov, \{Firudin I.\} and Tuncer H{\"o}kelek and Shuvalova, \{Elena V.\} and Samigullina, \{Aida I.\} and Ekberov, \{Nizami A.\} and Hasanov, \{Khudayar I.\} and Al-Douh, \{Mohammed Hadi\}",

year = "2025",

month = aug,

day = "1",

doi = "10.1107/S2414314625007205",

language = "English",

volume = "10",

pages = "x250720",

journal = "IUCrData",

issn = "2414-3146",

publisher = "International Union of Crystallography",

number = "Pt 8",

}

TY - JOUR

T1 - N-(4-Amino-1,2,5-oxadiazol-3-yl)formamide

AU - Guseinov, Firudin I.

AU - Hökelek, Tuncer

AU - Shuvalova, Elena V.

AU - Samigullina, Aida I.

AU - Ekberov, Nizami A.

AU - Hasanov, Khudayar I.

AU - Al-Douh, Mohammed Hadi

PY - 2025/8/1

Y1 - 2025/8/1

N2 - The asymmetric unit of the title compound, C3H4N4O2, contains two coplanar molecules (A and B) completely located on mirror planes. In the crystal, N—H· · ·O, N—H· · ·N, C—H· · ·O and C—H· · ·N hydrogen bonds link the molecules into sheets parallel to (010). There are neither significant π–π nor C—H· · ·π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packings of molecules A and B are from H· · ·O/O· · ·H (32.4% for A, 30.1% for B), H· · ·N/N· · ·H (28.2%, 31.5%) and H· · ·H (12.3%, 8.0%) interactions.

AB - The asymmetric unit of the title compound, C3H4N4O2, contains two coplanar molecules (A and B) completely located on mirror planes. In the crystal, N—H· · ·O, N—H· · ·N, C—H· · ·O and C—H· · ·N hydrogen bonds link the molecules into sheets parallel to (010). There are neither significant π–π nor C—H· · ·π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packings of molecules A and B are from H· · ·O/O· · ·H (32.4% for A, 30.1% for B), H· · ·N/N· · ·H (28.2%, 31.5%) and H· · ·H (12.3%, 8.0%) interactions.

KW - 2,2-dihalo-3-oxoaldehydes

KW - crystal structure

KW - non-covalent interactions

KW - pyrazol

UR - https://www.scopus.com/pages/publications/105015786409

U2 - 10.1107/S2414314625007205

DO - 10.1107/S2414314625007205

M3 - Article

C2 - 40917529

AN - SCOPUS:105015786409

SN - 2414-3146

VL - 10

SP - x250720

JO - IUCrData

JF - IUCrData

IS - Pt 8

M1 - x250720

ER -

N-(4-Amino-1,2,5-oxadiazol-3-yl)formamide

Abstract

Keywords

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