J Chem Crystallogr (2010) 40:909–913
913
8. Vashi K, Naik HB (2004) Eur J Chem 1:272
9. Joseyphus RS, Dharmaraj CJ, Nair MS (2006) Trans Met Chem
31:699
10. Chohan ZH, Pervez H, Rauf A, Khan KM, Supuran CT (2004) J
Enzym Inhib Med Chem 19:417
11. Katritzky AR, Rees CW (1984) Comprehensive heterocyclic
chemistry 6. Pergamon Press, New York; Toronto; Sydney; Paris,
p 250
12. Kabalka GW (1994) Current topics in the chemistry of boron.
The Royal Society of Chemistry, Cambridge, p 406
exhibit distorted tetrahedral configuration. The bond angles
of C7–N2–H2A (117.9°), C8–N2–H2A (120.5°) and
N2–C8–H8A (107.7, N2–C8–C9 (113.3) are significantly
smaller than that of 120.0°. The bond length of C7–N1
˚
(1.303 (2) A) is remarkably shorter than normal C–N
˚
(1.47 A) and close to the C=N double bond distance
˚
(1.308(7) A) [38], which is indicative of significant double
bond character. This shows a good agreement with the
expected values [39, 40]. The N2–C7 single bond length
˚
(1.337(2) A) is shorter than the reported values [39, 40],
¨
13. Bakhmutova EV, Noth H, Contreras R, Wrackmeyer B (2001) Z
Anorg Allg Chem 627:1846
14. Stoe & Cie (2002), X-AREA (Version 1.18) and X-RED32
(Version 1.04). Stoe&Cie, Darmstadt, Germany
which suggests the existence of a delocalized double bond
in the benzothiazole moiety. Although the N2–C8 bond
˚
distance (1.458 (2) A) is longer than a typical C=N bond
15. Sheldrick GM (1997) SHELXS–97, Program for the solution of
crystal structures. University of Goettingen, Germany
16. Sheldrick GM (1997) SHELXL–97, Program for the refinement
of crystal structures. University of Goettingen, Germany
17. Farrugia LJ (1997) J Appl Crystallogr 30:565
distance, it is shorter than a normal C–N. In compound 2
the phenol group seems to have a weak electron with-
drawing character. Thus, the length of N2–C7 and N2–C8
¨
18. Yıldız M, Kılıc¸ Z, Hokelek T (1998) J Mol Struct 441:1
¨
˚
bonds are shorter than a typical N–C (1.47 A) bond dis-
19. Nazır H, Yıldız M, Yılmaz H, Tahir MN, Ulku¨ D (2000) J Mol
Struct 524:241
tance. The single bond lengths of C8–C9 and C7–S1 are
˚
1.502(2), 1.761(1) A, respectively, which are longer than
20. Yeap GY, Ha ST, Ishizawa N, Suda K, Boey PL, Mahmood
WAK (2003) J Mol Struct 658:87
21. Salman SR, Shawkat SH, Al-Obaidi GM (1990) Can J Spectrosc
35:25
˚
typical C–C (1.54 A), and C–S (1.85 A) [41].
˚
Clearly, the amine form is favoured rather than the
22. Salman SR, Shawkat SH, Al-Obaidi GM (1989) Spectrosc Lett
22:1265
imine form for compound 2. These are evident from the
˚
observed C8–N2 bond distances of 1.458(2) A, which are
consistent with a single bond. However, the C7=N1 bond
¨
¨
23. Unver H, Yıldız M, Zengin DM, Ozbey S, Kendi E (2001) J
Chem Crystallogr 31:211
˚
distances are 1.303(2) A, and this is an indicative of a
24. Yıldız M (2004) Spectrosc Lett 37:367
¨
25. Unver H (2001) Spectrosc Lett 34:783
double bond.
26. Salman SR, Lindon JC, Farrant RD (1991) Spectrosc Lett
24:1071
27. Salman SR, Lindon JC, Farrant RD (1993) Magn Reson Chem
31:991
28. Salman SR, Kamounah FS (2002) Spectrosc Lett 35:327
Supplementary Material
¨
29. Unver H, Zengin DM, Gu¨ven K (2000) J Chem Crystallogr
Crystallographic data (excluding structure factors) for the
structure reported in this article have been deposited with
the Cambridge Crystallographic Data Centre as supple-
mentary publication number 689396. Copies of the data
can be obtained free of charge on application to CCDC12
Union Road, Cambridge CB21 EZ, UK (Fax: (?44) 1223-
336-033; e-mail: data_request@ccdc.cam.ac.uk).
30:359
¨
¨
¨
30. Unver H, Yıldız M, Du¨lger B, Ozgen O, Kendi E, Durlu TN
(2005) J Mol Struct 737:159
¨
¨
31. Yıldız M, Unver H, Du¨lger B, Erdener D, Ocak N, Erdonmez A,
Durlu TN (2005) J Mol Struct 738:253
¨
¨
32. Yıldız M, Unver H, Erdener D, Ocak N, Erdonmez A, Durlu TN
(2006) Cryst Res Technol 41:600
33. Bosshard C, Sutter K, Schlesser R, Gu¨nter P (1993) J Opt Soc Am
B10:867
34. Jacques J, Collet A, Willen SH (1981) Enantiomers, racemates
and resolutions. Wiley Interscience, New York, pp 1–23
¨
35. Kazak C, Aygu¨n M, Turgut G, Odabas¸oglu M, Ozbey S,
˘
Bu¨yu¨kgu¨ngor O (2000) Acta Crystallogr C56:1044
References
¨
¨
¨
36. Aygu¨n M, Is¸ık S¸, Ocal N, Tahir MN, Kaban S¸, Bu¨yu¨kgu¨ngor O
(1998) Acta Crystallogr C54:527
1. Borisenko VE, Koll A, Kolmakov EE, Rjasnyi AG (2006) J Mol
Struct 783:101
2. Ivanovskii VI (1978) Chemistry of hetero cyclic compounds.
High School Publishing House, Moscow
37. Sutton LE (1965) Chem Soc Spec Publ Suppl 18:516
¨
¨
¨
38. Unver H, Yıldız M, Kiraz A, Ocak N, Erdonmez A, Dulger B,
Durlu TN (2006) J Chem Crystallogr 36:229
¨
39. Bu¨yu¨kgu¨ngor O, C¸ alıs¸kan N, Davran C, Batı H (2004) Acta
Crystallogr E 60:o1414
3. Sharma RC, Varshney VK (1999) J Inorg Biochem 41:299
4. Vicini P, Geronikaki A, Incerti M, Busonera B, Poni G, Cabrasc
CA, Collac PL (2003) Bioorg Med Chem 11:4785
5. Konstantinivi SS, Radovanovi BC, Caki Z, Vasic V (2003) J Ser
Chem Soc 68:641
6. Anderson O (1999) Chem Rev 99:2683
7. Venugaopala KN, Jayashree BS (2003) Indian J Heterocycl Chem
12:307
40. Cui L, Yin H, Yang M, Quan L, Wang D (2008) Acta Crystallogr
E 64:o1974
41. Zhang G, Song B, Yang S, Jin L, Hu D, He W (2005) Anal Sci
21:105
123