4
M. Parveen et al. / Journal of Molecular Structure 1200 (2020) 127067
Table 1
Crystallographic data and structure refinement of compound (4a).
Empirical formula
Formula weight
Temperature (K)
Wavelength (Å)
Crystal system
Space group
a (Å)
C12H11NO4
233.22
293(2)
0.71073
Monoclinic
P21/c
8.3043(3)
b (Å)
14.7661(5)
c (Å)
9.5218(3)
a
b
g
(deg.)
(deg.)
(deg.)
90
111.319(2)
90
1087.69(7)
Volume (Å3)
Z
4
Calculated density (g/cm3)
Absorption coefficient (mmꢀ1
F(000)
1.424
0.108
488
)
Crystal size (mm)
0.53 ꢁ 0.22 ꢁ 0.20
q
range for data collection (deg.)
2.97e27.98
Index ranges
Reflections collected/unique
Completeness to
Refinement method
Data/restraints/parameters
Structure weighting factor
Goodness-of-fit on F2
ꢀ10 < h < 10, ꢀ19 < k < 19, ꢀ12 < l < 12
24008/2617 [R(int) ¼ 0.0110]
q
¼ 25.00ꢂ
99.7%
Full-matrix least-squares on F2
2617/0/159 w ¼ 1/[s2(Fo2)þ(0.1043P)2þ0.1068P] where P¼(Fo2þ2F2c)/3
1.036
Final R indices [I > 2
R indices (all data)
s
(I)]
R ¼ 0.0390wR ¼ 0.1147
R ¼ 0.0497wR ¼ 0.1280
0.244 and e 0.164
Largest diff. peak and hole (e Åe3
)
(ESI) m/z: 233.07 [M]þ.
.
3052 (¼C/H), 2988 (C/H), 1702 (C]O), 1600 (C]C), 1581,
1453,(C]C, C]N) 1346 (C]C), 1109, 1076 (CH). 1H NMR (400 MHz,
DMSO‑d6,
d, ppm): 2.32 (s, 3H, eCH3), 7.31e7.28 (m, 4H, eArH), 7.51
2.3.2. (4b) (Z)-3-methyl-4-((3-methylthiophen-2-yl)-methylene)-
isoxazol-5(4H)-one
(t, 1H, eArH), 9.65 (s, 1H, ]CH), 11.36 (s, 1H, eNH, D2O-
exchangeable). 13C NMR (100 MHz, DMSO‑d6,
d, ppm): 168.9 (C-5),
Crystallize from chloroform-methanol as a greenish yellow
solid, Yield: 95%, m. p: 170e172 ꢂC; Anal. Calcd. for C10H9NO2S: C,
57.95; H, 4.38; N, 6.76; O, 15.44; S, 15.47; found: C, 57.90; H, 4.28; N,
6.80; O, 15.56;, 15.68; FT-IR (KBr cmꢀ1): 3096 (C]H), 2924 (CeH),
1730 (C]O), 1610 (C]C), 1570, 1446 (C]Caromatic), 1434 (CH2), 1378
158.5 (C-3),137.9 (CH2),133.03 (C-80),129.2 (C-4), 129.8 (C-20),126.3
(C-70), 122.2 (C-60),120.1 (C-50), 119.3 (C-40), 111.6 (C-70), 110.6 (C-30),
15.2 (CH3). MS (ESI) m/z: 228.09 [M]þ.
.
(CH3), 1196 (CeO). 1H NMR (400 MHz, DMSO‑d6,
d, ppm): 2.3 (s, 3H,
2.3.5. (4e) (Z)-4-((5-bromofuran-2-yl-)-methylene)-3-
methylisoxazol-5(4H)-one
CH3), 2.5 (s, 3H, CH3), 7.2 (d, 1H, eArH, J ¼ 2.8 Hz), 7.9 (d, 1H, eArH,
J ¼ 3.1 Hz), 8.2 (s, 1H, ]CH). 13C NMR (100 MHz, DMSO‑d6,
d, ppm):
Crystallize from chloroform-methanol as a brown solid, Yield:
90%, m. p: 228e230 ꢂC; Anal. Calcd. for C9H6BrNO3: C, 42.22; H,
2.36; Br, 31.21; N, 5.47; O,18.75 found: C, 42.20; H, 2.40; Br, 31.15; N,
5.35; O, 18.78; FT-IR (KBr cmꢀ1): 3409 (]CH), 2926 (CH), 1705 (C]
O), 1612 (C]Caromatic), 1572, 1460 (C]C, C]N), 1174, 1019 (CH). 1H
168.8 (C-5), 161.2 (C-3), 153.1 (C-30), 139.7 (CH2), 138.8 (C-50), 131.8
(C-40), 130.5 (C-4), 111.2 (C-20), 14.8 (CH3), 11.01 (CH3). MS (ESI) m/z:
207.04 [M]þ.
.
2.3.3. (4c) (Z)-3-methyl-4-(pyridin-2-ylmethylene)-isoxazol-
5(4H)-one
NMR (400 MHz, DMSO‑d6, d, ppm): 2.45 (s, 3H, eCH3), 6.58 (d, 1H,
eArH, J ¼ 8 Hz), 7.78 (d, 1H, eArH, J ¼ 8 Hz), 7.35 (s, 1H, ]CH). 13
C
Crystallize from chloroform-methanol as a brownish red solid,
Yield: 93%, m. p: 208e210 ꢂC; Anal. Calcd. for C10H8N2O2: C, 63.82;
H, 4.28; N, 14.89; O, 17.00; found: C, 63.80; H, 4.25; N, 14.75; O,
16.90; FT-IR (KBr cmꢀ1): 3233 (]CH), 2924 (CH), 1712 (C]O), 1585,
1380 (C]Caromatic), 1145, 1102 (CeOeO). 1H NMR (500 MHz, CDCl3,
NMR (100 MHz, DMSO‑d6, d, ppm): 168.9 (C-5), 164.5 (C-3), 151.8
(C-20), 149.2 (CH2), 134.2 (C-4), 122.8 (C-50), 113.4 (C-30), 113.1 (C-40),
15.2 (CH3). MS (ESI) m/z: 254.95 [M]þ.
.
d
, ppm): 2.43 (s, 3H, eCH3), 7.65 (d, 1H, J ¼ 7.9, 4.7, 1.3 Hz), 7.93 (d,
2.3.6. (4f) (Z)-4-(4-(dimethylamino)-benzylidene)-3-
methylisoxazol-5(4H)-one
1H, eArH, J ¼ 7.9, 7.7, 1.8 Hz), 8.03 (d, 1H, eArH, J ¼ 7.7, 1.3, 0.5 Hz),
8.14 (s, 1H, ]CH), 8.79 (d, 1H, eArH, J ¼ 4.7, 1.8, 0.5 Hz). 13C NMR
Crystallize from chloroform-methanol as a shining red solid,
Yield: 90%, m. p: 220e222 ꢂC; [lit. [26] m. p. 225e227 ꢂC]; Anal.
Calcd. for C13H14N2O2: C, 67.81; H, 6.13; N, 12.17; O, 13.90; found: C,
67.70; H, 6.10; N, 12.20; O, 13.40; FT-IR (KBr cmꢀ1): 3080 (¼CH),
2915 (CH), 1716 (C]O), 1590, 1530 (C]C), 1300 (CeO). 1H NMR
(500 MHz, CDCl3, d
, ppm): 169.2 (C-5), 150.2 (C-3), 149.7 (C-20),
137.2 (C-60), 136.8 (CH2), 128.2 (C-40), 127.5 (C-4), 126.6 (C-30), 125.3
(C-50), 14.3 (CH3). MS (ESI) m/z: 188.06 [M]þ.
.
2.3.4. (4d) (Z)-4-(indolin-3-yl) methylene)-3-methylisoxazol-
5(4H)-one
Crystallize from chloroform-methanol as a yellowish solid,
Yield: 90%, m. p: 238e240 ꢂC; [lit [25]. m. p. 239e241 ꢂC]; Anal.
Calcd. for C13H10N2O2: C, 68.41; H, 5.30; N, 12.27; O, 14.02; found: C,
68.45; H, 5.25; N, 12.30; O, 14.10; FT-IR (KBr cmꢀ1): 3417(/NH),
(400 MHz, DMSO‑d6, d, ppm): 2.20 (s, 3H, eCH3), 3.13 (s, 6H, eCH3),
6.69 (dd, 2H, eArH, J ¼ 8 Hz), 7.17 (s, 1H, ]CH), 8.38 (d, 2H, eArH,
J ¼ 8 Hz);13C NMR (100 MHz, DMSO‑d6,
d, ppm): 168.6 (C-5), 161.7
(C-3), 153.1 (CH2), 139.72 (C-40), 138.8 (C-2' & C-60), 131.3 (C-4),
130.5.1 (C-10), 111.2 (C-3' & C-50), 14.6 (2 ꢁ CH3), 11.0 (CH3). MS (ESI)
m/z: 230.11 [M]þ.
.