2848
M. Akazome et al. / Tetrahedron 67 (2011) 2844e2848
8.02; N, 8.64. HRMS (ESI) calcd for C12H16N2O4Na (M[Thr-Phg]þ
Na)þ 275.1002, found 275.1001.
refined parameters, R1 (I>2.0
s
(I))¼0.0369, wR2 (all data)¼0.0834,
with heavy atoms refined anisotropically, residual electron density
0.213/ꢁ0.185.
Thr-Phg$cyclohexanol: colorless crystal, mp 151.1e151.4 ꢀC; 1H
NMR (CD3OD, 300 MHz):
d
(ppm)¼7.24e7.46 (m, 5H), 5.29 (s, 1H),
Crystallographic data (excluding structure factors) for the
structure in this paper have been deposited with the Cambridge
Crystallographic Data Centre as supplementary publication number
CCDC 801221-801224. Copies of the data can be obtained, free of
charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ,
4.12 (m, J¼6.3 Hz, 1H), 3.75 (d, J¼6.0 Hz, 1H), 3.52 (m, 1H), 1.86 (m,
2H), 1.74 (m, 2H), 1.58 (m, 1H), 1.35 (d, J¼6.3 Hz, 3H), 1.33 (d,
J¼6.3 Hz, 1H), 1.14e1.28 (m, 4H); 13C NMR (D2O, 75.5 MHz):
d
(ppm)¼176.0, 167.0, 138.0, 129.1, 128.3, 127.4, 70.4, 66.3, 60.0, 58.6,
34.4, 25.0, 23.9, 18.7. Anal. Calcd for C12H16N2O4$0.97(C6H12O)
$0.10H2O: C, 60.94; H, 7.99; N, 7.98. Found: C, 60.79; H, 8.00; N, 7.95.
HRMS (ESI) calcd for C12H16N2O4Na (M[Thr-Phg]þNa)þ 275.1002,
found 275.0999.
Acknowledgements
This work was supported by a Grant-in-Aid for Scientific
Research (C) (No. 21550129) from the Japan Society for the Pro-
motion Science.
4.5. Crystallograpic data for inclusion compounds
Data collection was performed on a Bruker APEXII CCD diffrac-
tometer with graphite-monochromated Mo K
a
(
l
¼0.71073) radia-
References and notes
tion. The structures weresolvedbya directmethodSHELXS-9715 and
refined by SHELXL-9716 in a computer program package from Bruker
AXS. Hydrogen atoms were calculated in appropriate position.
The inclusion compound of 1-propanol: C15H24N2O5, Mr¼312.36,
crystal dimensions 0.22ꢂ0.10ꢂ0.05 mm, orthorhombic, space
1. Separations and Reactions in Organic Supramolecular Chemistry; Perspectives
in Supramolecular Chemistry; Toda, F., Bishop, R., Eds.; John Wiley: West Sussex,
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2. (a) Aburaya, K.; Murai, T.; Hisaki, I.; Tohnai, N.; Miyata, M. Chem. Lett. 2008, 37,
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M. Enantiomer 2000, 5, 95e104; (d) Briozzo, P.; Kondo, T.; Sada, K.; Miyata, M.;
Miki, K. Acta Crystallogr., Sect. B 1996, 52, 728e733; (e) Sada, K.; Kondo, T.;
Miyata, M. Tetrahedron: Asymmetry 1995, 6, 2655e2656.
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Imai, Y.; Kawaguchi, K.; Sato, T.; Kuroda, R.; Matsubara, Y. Tetrahedron Lett.
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2941e2944; (g) Sada, K.; Shiomi, N.; Miyata, M. J. Am. Chem. Soc. 1998, 120,
10543e10544.
ꢀ
ꢀ
group P212121, T¼173 K, a¼8.4963(13) A, b¼9.1018(14) A, c¼22.062
3
ꢀ
ꢁ3
(4) A, V¼1706.1(5) A , Z¼4, Dc¼1.216 g cm
,
m
¼0.091 mmꢁ1, 4386
ꢀ
reflections collected, 1342 (Rint¼0.0370) independent reflections,
208 refined parameters, R1 (I>2.0
s
(I))¼0.0304, wR2 (all data)¼
0.0644, with heavy atoms refined anisotropically, residual electron
density 0.087/ꢁ0.112.
ꢁ
The inclusion compound of 2-propanol: C15H24N2O5, Mr¼312.36,
crystal dimensions 0.32ꢂ0.20ꢂ0.08 mm, monoclinic, space group
ꢀ
3
ꢀ
ꢀ
b
P21, T¼173 ꢀK, a¼8.5868(11) A, b¼9.0737(11) A, c¼11.3196(14) A,
¼
ꢁ3
m
103.465(2) , V¼857.71(18)A , Z¼2,Dc¼1.209 g cm
,
¼0.091 mmꢁ1
,
ꢀ
4810 reflections collected, 3292 (Rint¼0.0180) independent re-
flections, 206 refined parameters, R1 (I>2.0
s
(I))¼0.0411, wR2 (all
data)¼0.0984, with heavy atoms refined anisotropically, residual
electron density 0.352/ꢁ0.208.
6. (a) Akazome, M.; Takahashi, T.; Ogura, K. J. Org. Chem. 1999, 64, 2293e2300; (b)
Akazome, M.; Sumikawa, A.; Sonobe, R.; Ogura, K. Chem. Lett. 1996, 995e996.
The inclusion compound of 2-butanol: C16H26N2O5, Mr¼326.39,
crystal dimensions 0.40ꢂ0.23ꢂ0.16 mm, monoclinic, space group
€
€
7. (a) Gorbitz, C. H. Acta Crystallogr., Sect. B 2002, 58, 849e854; (b) Gorbitz, C. H.
€
Acta Crystallogr., Sect. C 1999, 55, 2171e2177; (c) Gorbitz, C. H. Acta Crystallogr.,
ꢀ
ꢀ
ꢀ
P21, T¼173 K, a¼8.5632(18) A, b¼9.0563(19) A, c¼11.866(3) A,
€
Sect. C 1999, 55, 670e672; (d) Gorbitz, C. H. Acta Crystallogr., Sect. B 1999, 55,
3
¼107.598(2)ꢀ, V¼877.1(3) A , Z¼2, Dc¼1.236 g cmꢁ3
,
m¼
ꢀ
€
104e113; (e) Gorbitz, C. H. Acta Chem. Scand. 1998, 52, 1343e1349.
b
ꢂꢂ ꢂ
8. Friscic, T.; Jones, W. Cryst. Growth Des. 2009, 9, 1621e1637.
0.092 mmꢁ1
,
4972 reflections collected, 3510 (Rint¼0.0259)
9. Akazome, M.; Ueno, Y.; Ooiso, H.; Ogura, K. J. Org. Chem. 2000, 65, 68e76.
independent reflections, 233 refined parameters, R1 (I>2.0
s(I))¼
€
€
10. (a) Gorbitz, C. H. Acta Crystallogr., Sect. C 2000, 56, 500e502; (b) Gorbitz, C. H.
Acta Crystallogr., Sect. C 2008, 64, o171eo176.
11. Akazome, M.; Hirabayashi, A.; Kataoka, K.; Nomura, S.; Ogura, K. Tetrahedron
2005, 61, 1107e1113.
12. Nozaki, S.; Muramatsu, I. Bull. Chem. Soc. Jpn. 1982, 55, 2165e2168.
13. Doyle, F. P.; Fosker, G. R.; Nayler, J. H.; Smith, H. J. Chem. Soc. 1962, 1440e1445.
14. Zervas, L.; Winitz, M.; Greenstein, J. P. J. Org. Chem. 1957, 22, 1515e1521.
15. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112e122 SHELXS97.
16. Sheldrick, G. M. SHELXTL Version 5.10; Bruker AXS: Madison, Wisconsin, USA,
1997.
0.0394, wR2 (all data)¼0.0975, with heavy atoms refined aniso-
tropically, residual electron density 0.583/ꢁ0.319.
The inclusion compound of cyclohexanol: C18H28N2O5, Mr¼352.42,
crystal dimensions0.37ꢂ0.29ꢂ0.12 mm, orthorhombic, space group
ꢀ
ꢀ
ꢀ
P212121, T¼173 K, a¼8.5464(9) A, b¼9.0873(9) A, c¼25.045(3) A,
3
ꢁ3
m
ꢀ
V¼1945.1(3) A , Z¼4, Dc¼1.203 g cm
,
¼0.088 mmꢁ1, 10938 re-
flections collected, 4399 (Rint¼0.0316) independent reflections, 231