8862
B.-Y. Lu et al. / Tetrahedron 68 (2012) 8857e8862
Rev. 2009, 38, 1726e1743; (f) Gan, Q.; Wang, Y.; Jiang, H. Curr. Org. Chem. 2011,
15, 1293e1301.
4. Wu, Y.-D.; Han, W.; Wang, D.-P.; Gao, Y.; Zhao, Y.-L. Acc. Chem. Res. 2008, 41,
1418e1427.
R1¼0.0511, wR2¼0.1166 (all data). Reflections collected/unique:
3087/1130 (Rint¼0.0934), GOF¼1.094.
5. (a) Gong, B. Chem.dEur. J. 2001, 7, 4336e4342; (b) Huc, I. Eur. J. Org. Chem.
2004, 17e29; (c) Li, Z.-T.; Hou, J.-L.; Li, C.; Yi, H.-P. Chem.dAsian. J. 2006, 1,
766e778; (d) Zhang, D.-W.; Zhao, X.; Hou, J.-L.; Li, Z.-T. Chem. Rev. http://dx.doi.
6. Pauling, L.; Delbruck, M. Science 1940, 92, 77e79.
7. Emsley, J. Chem. Soc. Rev. 1980, 9, 91e124.
8. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: New
York, NY, 1989.
9. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and
Biology; Oxford University: New York, NY, 1999.
10. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063e5070.
11. (a) Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565e573; (b) Desiraju, G. R. Chem.
Commun. 2005, 2995e3001.
4.3.2. Compound 2a. C14H9F2N3, M¼257.24, Triclinic, Space group
ꢀ
P-1, a¼5.8208(10), b¼7.3728(12), c¼13.821(2) A,
b¼96.202(3),
3
ꢁ3
ꢀ
V¼569.78(16) A , T¼293 K, Z¼2, Dc¼1.499 g cm
, m
¼0.115 mmꢁ1
,
€
F(000), 264, R1¼0.0553, wR2¼0.1638 (I>2
s
(I)), R1¼0.0590,
wR2¼0.1573 (all data). Reflections collected/unique: 3109/2187
(Rint¼0.0257), GOF¼1.048.
4.3.3. Compound 3a. C14H9F2N3, M¼257.24, Monoclinic, Space
ꢀ
group P2(1)/c, a¼13.417(2), b¼11.5535(19), c¼7.5275(12) A,
3
ꢁ3
ꢀ
b
¼90.189(3), V¼1166.8(3) A , T¼293 K, Z¼4, Dc¼1.464 g cm
,
m
¼0.113 mmꢁ1, F(000), 528, R1¼0.0635, wR2¼0.1723 (I>2
s (I)),
12. (a) Steiner, T. Crystallogr. Rev. 1996, 6, 1e51; (b) Wahl, M. C.; Sundaralingam, M.
Trends Biochem. Sci. 1997, 22, 97e102.
R1¼0.0770, wR2¼0.1619 (all data). Reflections collected/unique:
5949/2167 (Rint¼0.1534), GOF¼0.993.
13. Hunter, C. A. Angew. Chem., Int. Ed. 2004, 43, 5310e5324.
14. (a) Li, Z.-T.; Hou, J.-L.; Li, C. Acc. Chem. Res. 2008, 41, pp 1343e1353; (b) Zhao, X.;
Li, Z.-T. Chem. Commun. 2010, 1601e1616; (c) Zhu, Y.-Y.; Wang, G.-T.; Li, Z.-T.
Curr. Org. Chem. 2011, 15, 1266e1292; (d) Li, Z.-T. Huaxue Jinzhan 2011, 23, 1e12;
(e) Li, Z.-T.; Zhang, K.-D.; Shi, Z.-M.; Wang, L.; Zhou, C.; Lu, B.-Y. Pure Appl. Chem.
2012, 84, 965e978.
15. Foldamers: Structure, Properties and Applications; Hecht, S., Huc, I., Eds.; Wiley-
VCH: Weinheim, 2007.
16. (a) Howard, H. A. K.; Hoy, V. J.; O’Hagan, D.; Smith, G. T. Tetrahedron 1996, 52,
12613e12622; (b) Dunitz, J. D.; Taylor, R. Chem.dEur. J. 1997, 3, 89e98; (c)
Dunitz, J. D. ChemBioChem 2004, 5, 614e621.
17. (a) Zhao, X.; Wang, X.-Z.; Jiang, X.-K.; Chen, Y.-Q.; Li, Z.-T.; Chen, G.-J. J. Am.
Chem. Soc. 2003, 125, 15128e15139; (b) Li, C.; Ren, S.-F.; Hou, J.-L.; Yi, H.-P.; Zhu,
S.-Z.; Jiang, X.-K.; Li, Z.-T. Angew. Chem., Int. Ed. 2005, 44, 5725e5729; (c) Li, C.;
Zhu, Y.-Y.; Yi, H.-P.; Li, C.-Z.; Jiang, X.-K.; Li, Z.-T. Chem.dEur. J. 2007, 13,
9990e9998; (d) Zhu, Y.-Y.; Wu, J.; Li, C.; Zhu, J.; Hou, J.-L.; Li, C.-Z.; Jiang, X.-K.;
Li, Z.-T. Cryst. Growth Des. 2007, 7, 1490e1496; (e) Zhu, Y.-Y.; Li, C.; Li, G.-Y.; Jiang,
X.-K.; Li, Z.-T. J. Org. Chem. 2008, 73, 1745e1751.
4.3.4. Compound 4a. C14H9F2N3, M¼257.24, Monoclinic, Space
ꢀ
group C2/c, a¼27.993(4), b¼5.6987(8), c¼7.3154(10)A,
b
¼103.827(2),
3
ꢁ3
ꢀ
V¼1133.2(3) A , T¼293 K, Z¼4, Dc¼1.508 g cm
, m
¼0.116 mmꢁ1
,
F(000), 528, R1¼0.0498, wR2¼0.1690 (I>2
s
(I)), R1¼0.0533,
wR2¼0.1647 (all data). Reflections collected/unique: 3041/1169
(Rint¼0.0220), GOF¼1.130. Disorders at N-1 and C-4 were found.
4.3.5. Compound 3b. C14H9Cl2N3, M¼290.14, Monoclinic, Space
ꢀ
group P2(1)/n, a¼4.0145(18), b¼27.862(12), c¼11.598(5) A,
3
ꢁ3
,
s (I)),
ꢀ
b
¼92.220(6), V¼1296.3(10) A , T¼293 K, Z¼4, Dc¼1.487 g cm
m
¼0.488 mmꢁ1, F(000), 592, R1¼0.0749, wR2¼0.1898 (I>2
R1¼0.1032, wR2¼0.1736 (all data). Reflections collected/unique:
18. (a) Gan, Q.; Bao, C.; Kauffmann, B.; Grelard, A.; Xiang, J.; Liu, S.; Huc, I.; Jiang, H.
Angew. Chem., Int. Ed. 2008, 47, 1715e1718; (b) Gan, Q.; Ferrand, Y.; Bao, C.;
5524/2479 (Rint¼0.0364), GOF¼0.992.
ꢁ
Kauffmann, B.; Grelard, A.; Jiang, H.; Huc, I. Science 2011, 331, 1172e1175.
19. (a) Bao, C.; Kauffmann, B.; Gan, Q.; Srinivas, K.; Jiang, H.; Huc, I. Angew. Chem.,
Int. Ed. 2008, 47, 4153e4156; (b) Bao, C.; Gan, Q.; Kauffmann, B.; Jiang, H.; Huc, I.
Chem.dEur. J. 2009, 15, 11530e11536; (c) Ferrand, Y.; Gan, Q.; Kauffmann, B.;
Jiang, H.; Huc, I. Angew. Chem., Int. Ed. 2011, 50, 7572e7575.
20. (a) Ren, C.; Xu, S.; Xu, J.; Chen, H.; Zeng, H. Org. Lett. 2011, 13, 3840e3843; (b)
Ren, C.; Zhou, F.; Qin, B.; Ye, R.; Shen, S.; Su, H.; Zeng, H. Angew. Chem., Int. Ed.
2011, 50, 10612e10615.
21. (a) Zhu, Y.-Y.; Yi, H.-P.; Li, C.; Jiang, X.-K.; Li, Z.-T. Cryst. Growth Des. 2008, 8,
1294e1300; (b) Zhu, Y.-Y.; Jiang, L.; Li, Z.-T. CrystEngComm 2009, 11, 235e238.
22. Gan, Q.; Li, F.; Li, G.; Kauffmann, B.; Xiang, J.; Huc, I.; Jiang, H. Chem. Commun.
2010, 297e299.
23. Zhu, Y.-Y.; Wang, G.-T.; Wang, R.-X.; Li, Z.-T. Cryst. Growth Des. 2009, 9,
4778e4783.
4.3.6. Compound 4b. C14H9Cl2N3, M¼290.54, Monoclinic, Space
ꢀ
group C2/c, a¼30.701(5), b¼5.6709(9), c¼7.3915(12) A,
b¼98.819(5),
3
ꢁ3
m
ꢀ
V¼1271.7(4) A , T¼293 K, Z¼4, Dc¼1.518 g cm
,
¼0.498 mmꢁ1
,
F(000), 592, R1¼0.0486, wR2¼0.1538 (I>2
s
(I)), R1¼0.0549,
wR2¼0.1383 (all data). Reflections collected/unique: 3428/1374
(Rint¼0.0597), GOF¼1.085. Disorders at N-1 and C-4 were found.
4.3.7. Compound 4c. C14H9Br2N3, M¼379.06, Monoclinic, Space
ꢀ
group C2/c, a¼32.028(6), b¼5.6282(10), c¼7.4518(13)A,
b
¼98.685(3),
3
ꢀ
ꢁ3
V¼1327.8(4) A , T¼293 K, Z¼4, Dc¼1.896 g cm
, m
¼6.093 mmꢁ1
,
24. Zornik, D.; Meudtner, R. M.; Malah, T. E.; Thiele, C. M.; Hecht, S. Chem.dEur. J.
2011, 17, 1473e1484.
F(000), 740, R1¼0.0704, wR2¼0.1885 (I>2
s
(I)), R1¼0.0784,
25. Intermolecular CeH/Clꢁ hydrogen bonding has been investigated for tri-
azole oligomers, see: (a) Hua, Y.; Flood, A. H. Chem. Soc. Rev. 2010, 39,
1262e1271; (b) Li, Y.; Flood, A. H. Angew. Chem., Int. Ed. 2008, 47,
2649e2652; (c) Lee, S.; Hua, Y.; Park, H.; Flood, A. H. Org. Lett. 2010, 12,
2100e2102; (d) Juwarker, H.; Lenhardt, J. M.; Pham, D. M.; Craig, S. L. Angew.
Chem., Int. Ed. 2008, 47, 3740e3743; (e) Juwarker, H.; Lenhardt, J. M.; Castillo,
J. C.; Zhao, E.; Krishnamurthy, S.; Jamiolkowski, R. M.; Kim, K.-H.; Craig, S. L.
J. Org. Chem. 2009, 74, 8924e8934; (f) Meudtner, R. M.; Hecht, S. Angew.
Chem., Int. Ed. 2008, 47, 4926e4930; (g) Ostermeier, M.; Berlin, M.-A.;
Meudtner, R.; Demeshko, S.; Meyer, F.; Limberg, C.; Hecht, S. Chem.dEur. J.
2010, 16, 10202e10213; (h) Piot, L.; Meudtner, R. M.; El Malah, T.; Hecht, S.;
Samori, P. Chem.dEur. J. 2009, 15, 4788e4792; (i) Wang, Y.; Li, F.; Han, Y.;
Wang, F.; Jiang, H. Chem.dEur. J. 2009, 15, 9424e9433; (j) Wang, Y.; Xiang,
J.; Jiang, H. Chem.dEur. J. 2011, 17, 613e619.
wR2¼0.1829 (all data). Reflections collected/unique: 3440/1303
(Rint¼0.1054), GOF¼1.011. Disorders at N-1 and C-4 were found.
4.3.8. Compound 5. C14HF10N3, M¼401.18, Monoclinic, Space group
ꢀ
P2(1)/c, a¼14.2193(12), b¼10.5291(9), c¼9.0845(8) A,
b
¼91.433(2),
3
ꢀ
ꢁ3
m
V¼1359.7(2) A , T¼293 K, Z¼4, Dc¼1.960 g cm
,
¼0.216 mmꢁ1
,
F(000), 784, R1¼0.0436, wR2¼0.1167 (I>2
s
(I)), R1¼0.0504,
wR2¼0.1117 (all data). Reflections collected/unique: 6928/2526
(Rint¼0.0925), GOF¼1.038.
Acknowledgements
26. (a) You, L.-Y.; Chen, S.-G.; Zhao, X.; Liu, Y.; Zhang, Y.; Lu, H.-J.; Cao, C.-Y.; Li, Z.-T.
Angew. Chem., Int. Ed. 2012, 51, 1657e1661; (b) Wu, C.-F.; Zhao, X.; Lan, W.-X.;
Cao, C.; Liu, J.-T.; Jiang, X.-K.; Li, Z.-T. J. Org. Chem. 2012, 77, 4261e4270.
27. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int.
Ed. 2002, 41, 2596e2599; (b) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org.
Chem. 2002, 67, 3057e3064.
We thank the National Science Foundation of China (20974118)
for financial support.
References and notes
28. For reviews on intermolecular CeH/X (X¼F, Cl) hydrogen bonding, see: (a)
€
€
Reichenbacher, K.; Suss, H. I.; Hulliger, J. Chem. Soc. Rev. 2005, 34, 22e30; (b)
Hathwar, V. R.; Roopan, S. M.; Subashini, S. T.; Khan, F.; Row, T. N. G. J. Chem. Sci.
2010, 122, 677e685; (c) Rathore, R. S.; Karthikeyan, N. S.; Alekhya, Y.; Sa-
thiyanarayanan, K.; Aravindan, P. G. J. Chem. Sci. 2011, 123, 403e409; (d) Cho-
pra, D.; Guru Row, T. N. CrystEngComm 2011, 13, 2175e2186.
1. (a) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer:
Berlin, 1991; (b) Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford
University: New York, NY, 1997.
2. (a) Nangia, A. CrystEngComm 2002, 4, 93e101; (b) Biradha, K. CrystEngComm
2003, 5, 374e384; (c) Desiraju, G. R. Angew. Chem., Int. Ed. 2007, 46, 8342e8356.
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S. H. Acc. Chem. Res. 1998, 31, 173e180; (c) Goodman, C. M.; Choi, S.; Shandler,
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D. Acc. Chem. Res. 2008, 41, 1428e1438; (e) Saraogi, I.; Hamilton, A. D. Chem. Soc.
29. Holub, J. M.; Kirshenbaum, K. Chem. Soc. Rev. 2010, 39, 1325e1337.
30. Zhu, J.; Lin, J.-B.; Xu, Y.-X.; Shao, X.-B.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc.
2006, 128, 12307e12313.
31. (a) Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38,
ꢁ
386e395; (b) Erdelyi, M. Chem. Soc. Rev. 2012, 41, 3547e3557.