HETEROCYCLES, Vol. 87, No. 6, 2013
1297
dl-2,2’-Diphenyl-3,3’-bis(4-chlorophenylimino)-[2,2’-biindan]-1,1’-dione (dl-2): yield 24%. yellow
+
-1 1
blocks. mp 226 C; MS m/z 660 (M ); IR (Nujol) 1662, 1728 cm ; H NMR (CDCl ) 6.26 (4H, broad
3
doublet), 6.95 (2H, d, J = 7.4 Hz), 7.20 (4H, d, J = 7.9 Hz), 7.31 (2H, t, J = 7.4 Hz), 7.33 (4H, t, J = 7.0
Hz), 7.36 (2H, t, J = 7.0 Hz), 7.49 (2H, t, J = 7.6 Hz), 7.58 (4H, d, J = 7.9 Hz), 7.79 (2H, d, J = 7.6 Hz);
1
3
C NMR (CDCl ) 116.92, 122.34, 123.85, 125.15, 126.49, 127.49, 127.59, 127.71, 129.03, 129.92,
3
1
3
31.36, 131.70, 135.36, 140.19, 146.05, 165.57, 193.86. Anal. Calcd for C H Cl N O : C, 76.25; H,
42
26
2
2
2
.96; N, 4.24. Found (for solids desolvated in vacuo): C, 75.98; H, 4.31; N, 4.39.
meso-2,2’-Diphenyl-3,3’-bis(4-chlorophenylimino)-[2,2’-biindan]-1,1’-dione (meso-2): yield 16%.
+
-1 1
yellow blocks. decom. temp. 223 C; MS m/z 660 (M ); IR (Nujol) 1660, 1733, 1718 cm ; H NMR
(
CDCl ) 6.65 (4H, broad d), 6.66 (2H, d, J = 7.6 Hz), 7.2–7.3 (12H, m), 7.46 (2H, t, J = 7.5 Hz), 7.52
3
1
3
(
4H, d, J = 7.4 Hz), 7.88 (2H, d, J = 7.5 Hz); C NMR (CDCl ) 118.70, 124.08, 126.61, 126.83, 128.07,
3
1
28.22, 128.30, 128.86, 129.69, 130.94, 132.30, 132.50, 134.25, 149.20. Anal. Calcd for C H Cl N O :
42 26 2 2 2
C, 76.25; H, 3.96; N, 4.24. Found: C, 75.67; H, 4.23; N, 4.40.
dl-2,2’-Diphenyl-3,3’-bis(4-methoxyphenylimino)-[2,2’-biindan]-1,1’-dione (dl-3): yield 35%. yellow
+
-1 1
blocks. decom. temp. 224 C: MS m/z 652 (M ); IR (Nujol) 1651, 1724 cm ; H NMR (CDCl ) 3.80
3
(6H, s), 6.27 (4H, d, J = 8.0 Hz), 6.77 (4H, A B ), 6.99 (2H, d, J = 7.4 Hz), 7.26 (2H, t, J = 7.4 Hz), 7.28
2 2
(
4H, t, J = 7.9 Hz), 7.36 (2H, t, J = 8.0 Hz), 7.44 (2H, t, J = 7.5 Hz), 7.61 (4H, A B ), 7.77 (2H, d, J = 7.5
2
2
1
3
Hz); C NMR (CDCl ) 114.60, 118.76, 123.99, 125.79, 126.93, 128.16, 128.32, 131.08, 132.40, 132.67,
3
1
33.28, 137.54, 142.09, 142.90, 156.40, 167.18, 196.29. Anal. Calcd for C H N O : C, 80.96; H, 4.94;
44 32 2 4
N, 4.29. Found (for solids desolvated in vacuo): C, 80.65; H, 4.81; N, 4.32.
The X-ray crystallographic data were collected at on a Rigaku AFC 5S diffractometer, using graphite
monochromated Mo-K radiation (= 0.71075 Å). Crystal data for 1b: C H NO, P2 /n (#14), a =
22
17
1
o
3
3
1
2.895(4), b = 10.479(4), c = 13.222(4) Å, = 114.279(13) , V = 1628.7(9) Å , Z = 4, D = 1.270 g/cm ,
calc
R = 0.0328, wR = 0.0609, GOF = 1.106. Crystal data for 1c: C H NO , Pbcn (#60), a = 9.528(4), b =
1
2
22 17
2
3
3
1
4.187(5), c = 24.920(9) Å, V = 3368.7(21) Å , Z = 8, D = 1.291 g/cm , R = 0.0988, wR = 0.2107,
calc 1 2
GOF = 1.056. Crystal data for dl-2(MeCN): C H Cl N O , P2 /n (#14), a = 13.049(3), b = 13.255(2),
4
4
29
2
3
2
1
o
3
3
c = 20.671(5) Å, = 105.610(9) , V = 3443.3(13) Å , Z = 4, D = 1.355 g/cm , R = 0.0408, wR =
calc
1
2
0
1
0
.0889, GOF = 1.016. Crystal data for dl-3(MeCN): C H N O , P2 /n (#14), a = 12.9391(3), b =
46 35 3 4 1
o
3
3
3.2480(3), c = 20.5249(4) Å,= 103.043(7) , V = 3427.57(11) Å , Z = 4, D = 1.344 g/cm , R =
calc
1
.0607, wR = 0.1540, GOF = 1.040. Crystallographic data have been deposited with the Cambridge
2
Crystallographic Data Centre as the following supplementary publication nos. 1b; CCDC 928984. 1c;
CCDC 928985. dl-2(MeCN); CCDC 928980. dl-3 (MeCN); CCDC 928981. Copies of the data can be