692
J Chem Crystallogr (2010) 40:691–695
X-Ray Structure Determination
H3C
H
The crystal of title molecule was mounted on goniometer
of a STOE IPDS 2 diffractometer with a graphite mono-
O
C
N
O
˚
chromatized Mo-Ka radiation (k = 0.71073 A). Data col-
H
O
N
lection, reduction and corrections for absorption and
decomposition were achieved using CrysAlis CCD, Cry-
sAlis RED [18]. The structure was solved by SHELXS-97
and refined with SHELXL-97 [19, 20]. The positions of the
H atoms bonded to C atoms were calculated (C–H distance
O
CH3
S
N
H
O
Enol-imine
˚
0.96 A), and refined using a riding model but The HO1
atom was found in a difference electron-density map at the
end of the refinement process as a small positive electron
density. The H atom displacement parameters were
restricted to be 1.2Ueq of the parent atom. All atoms
(except hydrogen) were located from a difference Fourier
map and refined anisotropically. The details of the X-ray
data collection, structure solution and structure refinements
are given in Table 1. Selected bond distances and angles
are listed in Table 2. The molecular structure with the
atom-numbering scheme is shown in Fig. 1 [21] and the
crystal packing of the compound is depicted in Fig. 2.
Crystallographic data (excluding structure factors) for the
structures reported in this paper has been deposited with
the Cambridge Crystallographic Data Centre as supple-
mentary publication no. CCDC 676751 [22].
H3C
H
O
C
N
O
H
O
N
O
CH3
S
N
H
O
Keto-amine
Scheme 1 Tautomerism of the title compound
were reported in cm-1 units. The UV–Visible spectra were
measured using a SHIMADZU 1208 series spectrometer.
Carbon, nitrogen and hydrogen analyses were performed
on a LECO CHNS-932 analyzer. Melting points were
measured on an Electro Thermal IA 9100 apparatus using
a capillary tube. LC mass spectra were obtained on an
AGILENT 1100 MSD spectrometer with an ion source
temperature of 240 ꢁC. Sulfamethoxazole(Roche) and
2-hydroxy-3-methoxybenzaldehyde, THF, CHCl3, EtOH,
benzene, DMSO were purchased from Merck (Germany).
Result and Discussion
1
FT-IR, H-NMR, 13C-NMR and UV–Visible
Spectroscopic Studies
The IR spectra of the compounds are given in synthetic
procedures. Vibration bands with the wave numbers of
3431 (mO–H), 3025 cm-1 (mC–H, Ar–H), 2923 (mC–H, OCH3),
1622 cm-1 (mC=N), 1508 cm-1 (mC=C), 1330 cm-1 (mC–O
,
Ar–O) and 1177 cm-1 (mC–O–Ar, Csp3–O–Csp3) were
observed for compound, respectively. The stretching fre-
quency observed at 2634 cm-1 in compound shows the
presence of O–HꢀꢀꢀN intramolecular hydrogen bond [11].
The C=N bond which is accountable partially for the
existence enol-imine form can also be inferred from the IR
spectra of compound. The compound with strong band at
1251 cm-1 possesses highest percentage of enol-imino
tautomer due to the stabilization of phenolic C–O bond
[23].
Synthesis of 4-(2-Hydroxy-3-
Methoxybenzylideneamino)-N-(5-Methylisoxazol-3-
yl)Benzenesulfonamide
Sulfamethoxazole (2.53 g; 1 9 10-2 mol) was added to a
dry THF (200 mL) solution of 2-hydroxy-3-methox-
ybenzaldehyde (1.52 g; 1 9 10-2 mol). The mixture was
stirred and heated for 2 h. Compound was obtained from
the evaporation of THF. It was crystallized from chloro-
form/n-heptane as a red crystal, m.p. 218–220 ꢁC, 3.49 g
(90%) yield. Found: C, 55.80; H, 4.42; N, 10.85. Calc. For
C18H17N3O5S; C, 55.80; H, 4.41; N, 10.85%. IR (KBr,
cm-1); mO–H; 3245 m, mN–H; 3151 w, mAr–H; 3070 w,
mC–H; 2927, 2826 w, mO–H…N; 2649 w, mC=N; 1623 s,
mC=C; 1581 s, mC–N; 1497 s, mC–O; 1336 m, mC–O–Ar;
1249 s, mC–O–N 1177s.
1
The H NMR data for compound show that the tauto-
meric equilibrium favours the enol-imine in DMSO. The
OH, N–H and azomethine protons are observed as singlet
d = 12.52, d = 11.50 and d = 8.96 ppm, respectively for
compound. The phenyl protons resonate at d = 6.91–
7.94 ppm multiplet, the OCH3 protons of the compound
123
Yildiz, Mustafa
