J Chem Crystallogr (2009) 39:898–901
901
Acknowledgments The authors are thankful to Department of
Science and Technology (DST), and SAIF, I.I.T. Madras, Chennai,
India for the X-ray data collection. MMJ thanks the University Grant
Commission (Western Regional Office), India for their support of
Minor Research Project F. no. 47-254/07.
between the calculated and observed geometry could be
related to the crystal packing in the molecules. However,
the observation of a collection of strong C–HÁÁÁS intra-
molecular hydrogen bond interactions, close C–HÁÁÁO
intramolecular contacts and weak O–Cg p-ring interactions
provide evidence of a collective effect of all of these
interactions on crystal packing in the unit cell.
References
After the calculation, the dihedral angle between the
mean planes of the thiazole, phenyl and benzyl groups and
the mean plane of the pyrimidine ring became 1.34°,
11.34°, 84.79°, respectively. This represents a change of
4.8(0)°, 4.5(0)° and 0.9(2)°, large for the thiazole and
phenyl groups and small for the benzyl group, each with
respect to the pyrimidine group. The angle between the
mean planes of the thiazole ring and phenyl ring changed
from 12.6(6)° in the crystal to 1.3(4)° after the calculation,
a difference of 11.3(2)°. The small change in the C3–C2–
C11–C16 torsion angle between the pyrimidine and benzyl
rings, from -115.1(2)° in the crystal to -154.3(1)o with
the DFT calculation, supports the absence of any signifi-
cant crystalline intermolecular interactions with the benzyl
ring. The changes in the angle between the crystalline and
DFT calculational mean planes of the thiazole and phenyl
rings with that of the pyrimidine ring, as seen above,
supports the observation that strong C–HÁÁÁS intramolecular
hydrogen bond interactions, close C–HÁÁÁO intramolecular
contacts and weak O–Cg p-ring interactions do, therefore,
collectively have a significant influence on the crystalline
environment of the title compound, C23H20N2O3S, (I) and
more specifically in this region of the molecule.
1. Rovnyak GC, Kimbali SD, Beyer B, Cucinotta G, Dimarco JD,
Hedberg J, Malley M, McCarthy JP, Zhang R, Moorland S (1995)
J Med Chem 38:119–129
2. Kappe CO (2000) Eur J Med Chem 35:1043–1052
3. Adams S, Robbins F-M, Chen D, Wagage D, Holbeck S, Morse
HC, Stroncek D, Marincola FM (2005) J Transl Med 3:11. doi:
4. Winter CA, Risley EA, Nuss GW (1962) Proc Soc Exp Biol Med
111:544–547
5. Jotani MM, Baldaniya BB (2006) Acta Cryst E62:o5871–o5873
6. Jotani MM, Baldaniya BB (2007) Acta Cryst E63:o1937–o1939
7. Jotani MM, Baldaniya BB (2008) Acta Cryst E64:o739
8. Baldaniya BB, Jotani MM (2008) Anal Sci 24:x217–x218 X-ray
Structure Analysis Online
9. Altomare A, Burla MC, Camalli M, Cascarano GL, Giacovazzo
C, Guagliardi A, Moliterni AGG, Polidori G, Spagna R (1999)
J Appl Cryst 32:115–119
10. Sheldrick GM (2008) Acta Cryst A64:112–122
11. Bruker S (2004) SADABS. Bruker AXS, Madison
12. Spek AL (2003) J Appl Cryst 36:7–13
13. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354–1358
14. Allen FH (2002) Acta Cryst B58:380–388
15. Fischer A, Yathirajan HS, Mithun A, Bindya S, Narayana B
(2007) Acta Cryst E63:o1224–o1225
16. Sridhar B, Ravikumar K, Sadanandam YS (2006) Acta Cryst
C62:o687–o690
17. Bernstein J, Davis RE, Shimoni L, Chang NL (1995) Ang Chem
Int Ed Eng 34:1555–1573
18. Schmidt JR; Polik WF (2007) WebMO Pro, version 8.0.010e;
WebMO, LLC: Holland, MI, USA; available from http://www.
19. Frisch MJ et al. (2004) Gaussian 03, Revision C01, Wallingford,
CT
20. Becke AD (1998) Phys Rev A38: 3098
Supporting Information Available
X-ray crystallographic files, in Cif format, for the structure
determinationsof(I) (CCDC 714517) has beendeposited with
the Cambridge Crystallographic Date Center, CCDC: 26091.
Copies of this information may be obtained free of charge
from the Director, CCDC, 12 Union Road, Cambridge, CB2
1EZ (fax: ?44-1223-336033; email:deposit@ccdc.cam.uk or
21. Becke AD (1993) J Chem Phys 98: 648
22. Lee C, Yang W, Parr RG (1988) Phys Rev B37: 785
23. Hehre WJ, Random L, Schleyer PvR, Pople JA (1986) Ab initio
molecular orbital theory. Wiley, New York
123