Crystal Growth & Design
ARTICLE
(2) Taurog, A.; Dorris, M. L. Endocrinology 1988, 122, 592.
(3) Taurog, A. Endocrinology 1976, 98, 1031.
(4) Taurog, A.; Dorris, M. L.; Guziec, F. S., Jr. Endocrinology 1989,
temperature. After the mixture was stirred for 30 min, the reaction
mixture was extracted with deoxygenated dichloromethane (20 mL).
This solution containing compound MSeI (0.62 mmol, assuming 100%
conversion) was cooled to ∼5 °C and then added dropwise with bromine
(25 mg, 0.16 mmol) via syringe. The resultant orange colored, hetero-
geneous mixture was stirred for 1 h at ∼5 °C. The solvent was removed
under reduced pressure to afford an orange solid. Crystals suitable for
single crystal X-ray diffraction study were obtained from a dichloro-
methane solution by slow evaporation method. Yield: 95 mg (62%).
Synthesis of Complex 10. Toa solutionof4(100mg, 0.39 mmol)
in CH2Cl2 (10 mL) was added a solution of Br2 (65 mg, 0.39 mmol) in
CH2Cl2 (25 mL) dropwise under nitrogen at 0 °C. The red brown
solution was stirred at room temperature for 3 h. The resulting solution
was concentrated to afford a red brown solid product in a quantitative
yield. The product was recrystallized from CH2Cl2 to obtain black
crystals. Yield: 80 g (76%).
Synthesis of Complex 11. Toa solutionof4(100mg, 0.39 mmol)
in CH2Cl2 (10 mL) was added a solution of I2 (99 mg, 0.39 mmol) in
CH2Cl2 (25 mL) dropwise under nitrogen at 0 °C. The red brown
solution was stirred at room temperature for 3 h. The resulting solution
was concentrated to obtain a red brown solid product in a quantitative
yield. The product was recrystallized from CH2Cl2 to afford black
crystals. Yield: 90 g (80%).
Synthesis of Complex 12. To a solution LPO/H2O2/KI in
phosphate buffer (50 mM, pH 7.4),40 a methanolic solution of com-
pound 3 was added dropwise with stirring. The final mixture was allowed
to stand at room temperature for slow evaporation of the solvent. Upon
evaporation of the solvent, bright orange crystals were obtained.
X-ray Crystallography. X-ray crystallographic studies were carried
out on a Bruker CCD diffractometer with graphite-monochromatized
MoꢀKR radiation (λ = 0.71073 Å) controlled by a Pentium-based PC
running on the SMART software package.41ꢀ44 Single crystals were
mounted at room temperature on the ends of glass fibers and data were
collected at room temperature. The structures were solved by direct
methods and refined using the SHELXTL software package.42,43 All non-
hydrogen atoms were refined anisotropically and hydrogen atoms were
assigned to idealized locations. Empirical absorption corrections were
applied to all structures using SADABS.45 The structures were solved by
direct method (SIR-92)46 and refined by full-matrix least-squares proce-
dure on F2 for all reflections (SHELXL-97).42ꢀ44
124, 30.
(5) Taurog, A.; Dorris, M. L.; Lamas, L. Endocrinology 1974, 94, 1286.
(6) Nakashima, T.; Taurog, A.; Riesco, G. Endocrinology 1978, 103,
2187.
(7) Engler, H.; Taurog, A.; Nakashima, T. Biochem. Pharmacol. 1982,
31, 3801.
(8) Lee, E.; Miki, Y.; Katsljra, H.; Kariya, K. Biochem. Pharmacol.
1990, 39, 1467.
(9) Taurog, A.; Howells, E. J. Biol. Chem. 1966, 241, 1329.
(10) Engler, H.; Taurog, A.; Luthy, C.; Dorris, M. L. Endocrinology
1983, 112, 86.
(11) Shiroozu, A.; Taurog, A.; Engler, H.; Dorris, M. L. Endocrinol-
ogy 1983, 113, 362.
(12) Magnusson, R. S.; Taurog, A. Biochem. Biophys. Res. Commun.
1983, 112, 475.
(13) Magnusson, R. P.; Taurog, A.; Dorris, M. L. J. Biol. Chem. 1984,
259, 13783.
(14) Magnusson, R. P.; Taurog, A.; Dorris, M. L. J. Biol. Chem. 1984,
259, 197.
(15) Doerge, D. R. Biochemistry 1986, 25, 4724.
(16) Doerge, D. R. Arch. Biochem. Biophys. 1986, 244, 678.
(17) Doerge, D. R. Biochemistry 1988, 27, 3697.
(18) Buxeraud, J.; Absil, A. C.; Claude, J.; Raby, C.; Catanzano, G.;
Beck, C. Eur. J. Med. Chem. 1985, 20, 43.
(19) Raby, C.; Lagorce, J. F.; Jambut-Absil, A. C.; Buxeraud, J.;
Catanzano, G. Endocrinology 1990, 126, 1683.
(20) Lagorce, J.; Buxeraud, J.; Jambut-Absil, A.; Raby, C. Heterocycles
1990, 31, 1609.
(21) Jambut-Absil, A.; Buxeraud, J.; Lagorce, J.; Raby, C. Int. J.
Pharm. 1987, 35, 129.
(22) For further details about charge-transfer (CT) in the context of
the complexes under discussion here, see Aragoni, M. C.; Arca, M.;
Demartin, F.; Devillanova, F. A.; Garau, A.; Isaia, F.; Lippolis, V.; Verani,
G. Coord. Chem. Rev. 1999, 184, 271.
(23) Cristiani, F.; Devillanova, F.; Isaia, F.; Lippolis, V.; Verani, F.
Polyhedron 1995, 14, 2937.
(24) Aragoni, M. C.; Arca, M.; Demartin, F.; Devillanova, F.; Garau,
A.; Isaia, F.; Lelj, F.; Lippolis, V.; Verani, G. Chem.—Eur. J. 2001,
7, 3122.
(25) (a) Aragoni, M. C.; Arca, M.; Demartin, F.; Devillanova, F. A.;
Garau, A.; Isaia, F.; Lippolis, V.; Verani, G. J. Am. Chem. Soc. 2002,
124, 4538. (b) Arca, M.; Aragoni, M. C.; Devillanova, F.; Garau, A.;
Isaia, F.; Lippolis, V.; Mancini, A.; Verani, G. Bioinorg. Chem. Appln. 2006, 1.
(26) Demartin, F.; Devillanova, F. A.; Isaia, F.; Lippolis, V.; Verani,
G. Inorg. Chem. 1993, 32, 3694.
’ ASSOCIATED CONTENT
S
Supporting Information. X-ray crystallographic informa-
b
tion files (CIF) of complexes 8 and 10ꢀ12. This information is
(27) Demartin, F.; Devillanova, F.; Garau, A.; Isaia, F.; Lippolis, V.;
Verani, G. Polyhedron 1999, 18, 3107.
(28) (a) Nosco, D. L.; Heeg, M. J.; Glick, M. D.; Elder, R. C.;
Deutsch, E. J. Am. Chem. Soc. 1980, 102, 7784. (b) Daga, V.; Hadjikakou,
S. K.; Hadjiliadis, N.; Kubicki, M.; dos Santos, J. H. Z.; Butler, I. S. Eur. J.
Inorg. Chem. 2002, 2002, 1718. (c) Antoniadis, C. D.; Hadjikakou, S. K.;
Hadjiliadis, N.; Kubicki, M.; Butler, I. S. Eur. J. Inorg. Chem. 2004,
2004, 4324. (d) Antoniadis, C. D.; Hadjikakou, S. K.; Hadjiliadis, N.;
Kubicki, M.; Butler, I. S. New. J. Chem. 2005, 29, 714. (e) Corban, G. J.;
Hadjikakou, S. K.; Hadjiliadis, N.; Kubicki, M.; Tiekink, E. R. T.; Butler,
I. S.; Drougas, E.; Kosmas, A. M. Inorg. Chem. 2005, 44, 8617.
(29) Purcell, K. F.; Kotz, J. C. Inorganic Chemistry; Saunders:
Philadelphia, PA, 1977; p 209.
(30) Jemmis, E. D.; Giju, K. T.; Leszczynski, J. J. Phys. Chem., 1997,
101, 7389.
(31) Roy, G.; Nethaji, M.; Mugesh, G. Org. Biomol. Chem. 2006,
4, 2883.
(32) Bigoli, F.; Demartin, F.; Deplano, P.; Devillanova, F.; Isaia, F.;
Lippolis, V.; Mercuri, M.; Pellinghelli, M.; Trogu1c, E. Inorg. Chem.
1996, 35, 3194.
’ AUTHOR INFORMATION
Corresponding Author
*E-mail: mugesh@ipc.iisc.ernet.in.
’ ACKNOWLEDGMENT
This study is supported by the Department of Science and
Technology (DST), New Delhi, India. G.M. acknowledges the
DST for the award of Swarnajayanti fellowships, and G.R. and K.
P.B. thank the Council of Scientific and Industrial Research
(CSIR) for their research fellowships.
’ REFERENCES
(1) Davidson, B.; Soodak, M.; Neary, J. T.; Strout, H. V.; Kieffer,
J. D.; Mover, H.; Maloof, F. Endocrinology 1978, 103, 871.
2285
dx.doi.org/10.1021/cg101688v |Cryst. Growth Des. 2011, 11, 2279–2286