Abstract
The title compound (
3
), C
17
H
14
BrN
3
O
4
S, is a Schiff base compound of 5-bromosalicylaldehyde (
1
) and sulfamethoxazole (
2
). The structure of (
3
) was determined by spectral (IR,
1
H and
13
C NMR), elemental analyses and X-ray diffraction data. Compound (
3
) crystallizes in the monoclinic space group C2/c, with
a
= 31.936(3),
b
= 6.2571(5),
c
= 16.903(1) Å, β = 94.867(8),
V
= 3365.5(5) Å
3
,
Z
= 8. In the molecule of compound (
3
), the molecule is bent at the S atom with a C–SO
2
–NH–C torsion angle of −86.3(3)°. Pairs of molecules, related by inversion centres, form intermolecular N–H···N hydrogen bonds to produce a dimer. An intramolecular phenolic O–H···N hydrogen bond is also formed. Intermolecular hydrogen bonding and π–π stacking hold the molecules together. The average distance between stacked benzene ring planes is 3.625(2) Å.
Graphical Abstract