The title 4,4'-disubstituted diphenyl-1,3-triazines, C14H15N3, (I), C12H9ClFN3, (II), and C13H12FN3, (III), each contain a triazene group (-N=N-NH-) having an extended conformation. The dihedral angles between the two benzene rings in (I), (II) and (III) are 4.3, 3.4 and 6.5 degrees , respectively. The molecules are almost entirely planar, with maximum deviations from the mean planes of 0.1087 (2), -0.1072 (7) and 0.1401 (3) A, respectively. In each compound, the molecules are linked by N-H...N hydrogen bonds to form chains and pack similarly in the crystal structures.
In the title compound, C15H14N2O5, the benzene rings are nearly coplanar, making a dihedral angle of 4.89 (8)°. An intramolecular N—H...O hydrogen bond occurs between the imino and methoxy groups. In the crystal, weak C—H...O hydrogen bonds link the molecules into supramolecular chains propagating along thea-axis direction. π–π stacking is observed between parallel benzene rings of neighbouring chains, the centroid-to-centroid distance being 3.6491 (10) Å. Three-dimensional Hirshfeld surface analyses and two-dimensional fingerprint plots have been used to analyse the intermolecular interactions present in the crystal.
In this study, a
novel heterocyclic amide derivative,
N
-(3-cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide
(
I
), was obtained by reacting 2-aminothiophene-3-carbonitrile
with
activated 2-(thiophen-2-yl)acetic acid in a
N
-acylation
reaction and characterized by elemental analyses, FT-IR,
1
H and
13
C NMR spectroscopic studies, and single crystal
X-ray crystallography. The crystal packing of
I
is stabilized
by C–H···N and N–H···N
hydrogen bonds. In addition,
I
was investigated computationally
using the density functional theory (DFT) method with the B3LYP exchange
and correlation functions in conjunction with the 6311++G(d,p) basis
set in the gas phase. Fukui function (FF) analysis was also carried
out. Electrophilicity-based charge transfer (ECT) method and charge
transfer (Δ
N
) were computed to examine the
interactions between
I
and DNA bases (such as guanine,
thymine, adenine, and cytosine). The most important contributions
to the Hirshfeld surface are H···H (21%), C···H
(20%), S···H (19%), N···H (14%), and
O···H (12%). An ABTS antioxidant assay was used to
evaluate the in vitro antioxidant activity of
I
. The
compound exhibited moderate antioxidant activity. The antimicrobial
activity of the title molecule was investigated under aseptic conditions,
using the microdilution method, against Gram-positive and Gram-negative
bacterial strains, and it also demonstrated significant activity against
yeasts (
Candida glabrata
ATCC 90030,
Candida krusei
ATCC 34135). The findings revealed
that the molecule possesses significant antioxidant and antimicrobial
properties.
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