2
3
21
Z = 8, r = 1.325 g cm , m = 0.083 mm , T = 293 K, l(Mo-Ka) =
˚
.71073 A, data/parameters = 4850/298, converging to R
0
1
= 0.0554, wR
2
=
0.1236 (on 2475 I . s(I) observed data); R = 0.1310, wR
data), residual electron density: 0.135 e A
1
2
= 0.1538 (all
23
˚
.
{
{ Crystal data for 5: C26 , M = 411.44, monoclinic, P2
H
21
N
˚
1
O
4
1
/c (14), a =
˚
˚
1
2.140(5) A, b = 5.718(5) A, c = 29.183(5) A, b = 96.673(5)u, V =
3
23
21
˚
2012.06(23) A , Z = 4, r = 1.358 g cm , m = 0.092 mm , T = 293 K,
˚
l(Mo-Ka) = 0.71073 A, data/parameters = 3513/280, converging to R
.0429, wR = 0.1065 (on 2508 I . s(I) observed data); R = 0.0655, wR
.1211 (all data), residual electron density: 0.151 e A
{ Crystal data for 6: C36 , M = 523.62, monoclinic, P2
1
=
=
0
0
2
1
2
23
.
˚
{
H
29
N
˚
1
O
3
1
/c (14), a =
˚
˚
2
4.8660(4) A, b = 5.2750(2) A, c = 21.6140(11) A, b = 101.028(1)u, V =
3
23
21
˚
782.72(6) A , Z = 4, r = 1.25 g cm , m = 0.079 mm , T = 293 K, l(Mo-
2
˚
Ka) = 0.71073 A, data/parameters = 4894/477, converging to R
wR = 0.1227 (on 2316, I . 2s(I) observed data); R = 0.1623, wR
.1642 (all data), residual electron density: 0.143 e A . CCDC 615872–
15877. For crystallographic data in CIF or other electronic format see
DOI: 10.1039/b610565c
1
= 0.0646,
2
1
23
2
=
Fig. 3 Illustration of the edge-to-face packing observed between the
naphthalimide and naphthyl ether units in the crystal structures of (a)
molecule 4, (b) molecule 5 and (c) molecule 6.
˚
0
6
1
(a) C. A. Hunter and J. K. M. Sanders, J. Am. Chem. Soc., 1990, 112,
525–5534; (b) C. A. Hunter, K. R. Lawson, J. Perkins and C. J. Urch,
J. Chem. Soc., Perkin Trans. 2, 2001, 651–669.
Notes and references
5
{ X-Ray data were collected using a Nonius kappa-CCD diffractometer
˚
with Mo-Ka (l = 0.71073 A) as the incident radiation. Structures were
2 (a) R. S. Lokey and B. L. Iverson, Nature, 1995, 375, 303–305; (b)
D. T. McQuade, A. E. Pullen and T. M. Swager, Chem. Rev., 2000, 100,
2537–2574; (c) V. Percec, M. Glodde, T. K. Bera, Y. Miura,
I. Shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney,
I. Schnell, A. Rapp, H. W. Spiess, S. D. Hudson and H. Duan, Nature,
2002, 419, 384–387; (d) F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer and
A. Schenning, Chem. Rev., 2005, 105, 1491–1546; (e) W. Pisula,
M. Kastler, D. Wasserfallen, J. W. F. Robertson, F. Nolde, C. Kohl
and K. Mullen, Angew. Chem., Int. Ed., 2006, 45, 819–823.
solved using SIR 97 or SIR 92 and were refined by full-matrix least-squares
2
o
on F
§
using SHELXL97.
Crystal data for 1: C36H F N O , M = 649.55, triclinic, P1 (2), a =
¯
22 7 1 3
˚
˚
˚
5
8
.6784(8) A, b = 8.4377(11) A, c = 31.313(5) A, a = 87.186(6)u, b =
3 23
˚
7.102(5)u, c = 79.417(8)u, V = 1471.6 A , Z = 2, r = 1.466 g cm ,
21
˚
m = 0.123 mm , T = 293 K, l(Mo-Ka) = 0.71073 A, data/parameters =
147/469, converging to R = 0.0924, wR = 0.1918 (on 2667 I . 2s(I)
observed data); R = 0.1842, wR = 0.2428 (all data), residual electron
5
1
2
1
2
2
3
˚
3 (a) H. Spanggaard and F. C. Krebs, Sol. Energy Mater. Sol. Cells, 2004,
83, 125–146; (b) T. L. Benanti and D. Venkataraman, Photosynth. Res.,
2006, 87, 73–81.
density: 0.337 e A
¯
28 13 1 3
Crystal data for 2: C42H F N O , M = 841.65, triclinic, P1 (2), a =
.
"
˚
˚
˚
5
9
.8313(3) A, b = 8.9482(5) A, c = 36.8720(19) A, a = 90.655(2)u, b =
3 23
˚
4 (a) L. Schmidt-Mende, A. Fechtenkotter, K. Mullen, E. Moons,
R. H. Friend and J. D. MacKenzie, Science, 2001, 293, 1119–11221;
(b) J. Y. Becker, J. Bernstein, S. Bittner, N. Levi and S. S. Shaik, J. Am.
Chem. Soc., 1983, 105, 4468–4469; (c) J. Y. Becker, J. Bernstein, S. Bittner,
N. Levi, S. S. Shaik and N. Zerzion, J. Org. Chem., 1988, 53, 1689–1694.
5 (a) G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller,
E. B. Lobkovsky and R. H. Grubbs, J. Am. Chem. Soc., 1998, 120,
3641–3649; (b) M. Weck, A. R. Dunn, K. Matsumoto, G. W. Coates,
E. B. Lobkovsky and R. H. Grubbs, Angew. Chem., Int. Ed., 1999, 38,
2741–2745.
6 (a) J. D. Dunitz, A. Gavezzotti and W. B. Schweizer, HeIv. Chim. Acta,
2003, 86, 4073–4092; (b) L. Li and D. M. Collard, Macromolecules, 2005,
38, 372–378; (c) Z. B. Li, M. A. Hillmyer and T. P. Lodge, Nano Lett.,
2006, 6, 1245–1249; (d) T. P. Lodge, J. A. Bang, Z. B. Li, M. A. Hillmyer
and Y. Talmon, Faraday Discuss., 2005, 128, 1–12.
1.406(2)u, c = 104.355(2)u, V = 1863.03(17) A , Z = 2, r = 1.5 g cm ,
21
˚
m = 0.138 mm , T = 293 K, l(Mo-Ka) = 0.71073 A, data/parameters =
363/587, converging to R = 0.1008, wR = 0.2332 (on 3251 I . 2s(I)
observed data); R = 0.1775, wR
6
1
2
1
2
= 0.2773 (all data), residual electron
¯
32 13 1 5
H F N O , M = 829.65, triclinic, P1 (2), a =
2
3
˚
density: 0.372 e A
.
I Crystal data for 3: C38
˚
˚
˚
7
9
.9502(3) A, b = 9.5259(4) A, c = 49.289(2) A, a = 88.7490(10)u, b =
3 23
˚
0.2360(10)u, c = 87.669(2)u, V = 3728.8(3) A , Z = 4, r = 1.478 g cm ,
21
˚
m = 0.14 mm , T = 293 K, l(Mo-Ka) = 0.71073 A, data/parameters =
097/1024, converging to R = 0.1086, wR = 0.3114 (on 4134, I . 2s(I)
observed data); R = 0.1477, wR = 0.3534 (all data), residual electron
6
1
2
1
2
2
3
˚
density: 0.628 e A . The perfluorinated side chains are disordered. Refer
to the ESI{ for details.
** Crystal data for 4: C30H N O , M = 423.45, orthorhombic, Pcab (61),
a = 9.329(5) A, b = 17.981(5) A, c = 25.206(5) A, V = 4244.95(27) A ,
17 1 2
˚
3
˚
˚
˚
6
94 | Chem. Commun., 2007, 692–694
This journal is ß The Royal Society of Chemistry 2007