S. Lulin´ski, J. Serwatowski / Journal of Organometallic Chemistry 692 (2007) 2924–2929
2929
(ca. 15 mL), which was obtained by the addition of a few
References
drops of water to a reagent grade solvent [24]. The use of
dry EtOAc and other solvents (acetone, acetone + water)
did not afford crystals having a sufficient quality. All mea-
surements were performed on a KM4CCD j-axis diffrac-
tometer with graphite-monochromated Mo Ka radiation.
The crystal was positioned at 62 mm from the CCD cam-
era. 1500 frames were measured at 0.4ꢁ intervals with a
counting time of 18 s. The data were corrected for Lorentz
and polarization effects. Empirical correction for absorp-
tion was applied. Data reduction and analysis were carried
out with the Oxford Diffraction programs CrysAlis CCD
and CrysAlis RED, Version 1.171.28cycle2 beta.
[1] (a) For example, see: T. DoMinh, A.L. Johnson, J.E. Jones, P.P.
Senise Jr., J. Org. Chem. 42 (1977) 4217–4221;
(b) B.C. Uff, R.S. Budhram, G. Ghaem-Maghami, A.S. Mallard, V.
Harutunian, C. Seenevasagum, N. Choudhury, J. Kant, F.D. Popp,
J. Chem. Res. (M) 6 (1986) 1901–1930;
(c) Y.-M. Man, T.C.W. Mak, H.N.C. Wong, J. Org. Chem. 55 (1990)
3214–3221;
(d) M. Yasuda, T. Fujibayashi, I. Shibata, A. Baba, H. Matsuda, N.
Sonoda, Chem. Lett. (1995) 167–168.
[2] (a) K. Bowden, F.A. El-Kaissi, N.S. Nadvi, J. Chem. Soc., Perkin
Trans. 2 (1979) 642–645;
(b) R.S. McDonald, E.V. Martin, Can. J. Chem. 57 (1979) 506–516;
(c) N. Salem, P. Zuman, Anal. Chem. 78 (2006) 7802–7808.
[3] K. Bowden, F.A. El-Kaissi, R.J. Ranson, J. Chem. Soc., Perkin
Trans. 2 (1990) 2089–2092.
[4] S.E. Walsh, J.-Y. Maillard, C. Simons, A.D. Russell, J. Appl.
Microbiol. 87 (1999) 702–710.
[5] P. Zuman, Chem. Rev. 104 (2004) 3217–3238.
The structure 2-II was solved by direct methods [25] and
refined using SHELXL97. The refinement was based on F2 for
all reflections except those with very negative F2. Weighted
R factors wR and all goodness-of-fit S values are based on
F2. Conventional R factors are based on F with F set to
´
[6] M. Da˛browski, J. Kubicka, S. Lulinski, J. Serwatowski, Tetrahedron
P
zero for negative F2. The F o2 > 2 ðF 2oÞ criterion was used
only for calculating R factors and is not relevant to the
choice of reflections for the refinement. The R factors based
on F2 are about twice as large as those based on F. All
hydrogen atoms were located geometrically and their posi-
tions were refined. Temperature factors of three hydrogen
atoms were not refined. Scattering factors were taken from
Tables 6.1.1.4 and 4.2.4.2 [26]. The crystal was a pseudo-
merohedral twin with a refined component occupancy of
42.51(9)%. The twinning is due to the rotation around
the [100] direction by the angle of 180ꢁ, which is repre-
61 (2005) 6590–6595.
[7] H. No¨th, B. Wrackmeyer, in: P. Diehl, E. Fluck, R. Kosfeld (Eds.),
Nuclear Magnetic Resonance Spectroscopy of Boron Compounds,
Springer, Berlin, Heidelberg, New York, 1978, p. 18, 24.
[8] (a) J. Harron, R.A. McClelland, C. Thankachan, T. Tidwell, J. Org.
Chem. 46 (1981) 903–910;
(b) F.M. Hauser, P. Hewawasam, V.M. Baghdanov, J. Org. Chem.
53 (1988) 223–224;
(c) P.A. Leighton, F.A. Lucy, J. Chem. Phys. 2 (1934) 756–759.
[9] J. Kagan, J. Org. Chem. 32 (1967) 4060–4062.
[10] P. Tschampel, H.R. Snyder, J. Org. Chem. 29 (1964) 2168–2172.
[11] V.V. Zhdankin, P.J. Persichini III, L. Zhang, S. Fix, P. Kiprof,
Tetrahedron Lett. 40 (1999) 6705–6708.
[12] (a) V.L. Arcus, L. Main, B.K. Nicholson, J. Organomet. Chem. 460
(1993) 139–147;
ꢀ ꢀ ꢀ
sented by the matrix f100010101g. Another possibility
involves the rotation around the [102] direction by the
(b) L.-Y. Tan, A.J.P. White, D.E. Widdowson, R. Wilhelm, D.J.
Williams, J. Chem. Soc., Perkin Trans. 1 (2001) 3269–3280;
angle of 180ꢁ, which is represented by the matrix
ꢀ
ꢀ
´
´
(c) A. Sporzynski, M. Lewandowski, P. Rogowska, M.K. Cyranski,
Appl. Organomet. Chem. 19 (2005) 1202–1204;
(d) Y. Yamamoto, J. Ishii, H. Nishiyama, K. Itoh, J. Am. Chem.
Soc. 127 (2005) 9625–9631.
f100010101g.
Acknowledgements
[13] F. Anvia, K. Bowden, J. Chem. Soc., Perkin Trans. 2 (1990) 2093–
2097.
[14] W.H. Scouten, X.-C. Liu, N. Khangin, D.F. Mullica, E.L. Sappen-
field, J. Chem. Cryst. 24 (1994) 621–630.
This work was supported by the Warsaw University of
Technology. The support by Aldrich Chemical Co., Inc.,
Milwaukee, WI, through continuous donation of chemicals
and equipment is gratefully acknowledged. The X-ray anal-
ysis of 2-II was performed by Ł. Dobrzycki in the Crystal-
lographic Unit of the University of Warsaw. We express
special thanks to Dr. J. Zachara from our university for
the interpretation of crystal twinning in 2-II.
´
[15] S. Lulinski, I. Madura, J. Serwatowski, H. Szatyłowicz, J. Zachara,
New J. Chem. 31 (2007) 144–154.
[16] C.K. Fay, J.B. Grutzner, L.F. Johnson, S. Sternhell, P.W. Wes-
terman, J. Org. Chem. 38 (1973) 3122–3136.
[17] J.M. Sayer, J. Org. Chem. 40 (1975) 2545–2547.
[18] H. No¨th, B. Wrackmeyer, in: P. Diehl, E. Fluck, R. Kosfeld (Eds.),
Nuclear Magnetic Resonance Spectroscopy of Boron Compounds,
Springer, Berlin, Heidelberg, New York, 1978, p. 84.
[19] M. Dowlut, D.G. Hall, J. Am. Chem. Soc. 128 (2006) 4227–4228.
[20] A. Ricardo, F. Frye, M.A. Carrigan, J.D. Tipton, D.H. Powell, S.A.
Benner, J. Org. Chem. 71 (2006) 9503–9505.
[21] J.M. Breitenbach, R.P. Hausinger, Biochem. J. 250 (1988) 917–920.
[22] P.W. Austin, C.J. Kneale, P.J. Crowley, J.M. Clough, US Patent No.
5880188, 1999.
Appendix A. Supplementary material
CCDC 616906 contains the supplementary crystallo-
graphic data for 2-II. These data can be obtained free of
charge
via
[23] D. Stueber, D. Patterson, A.M. Orendt, D.M. Grant, R.W. Parry,
Inorg. Chem. 40 (2001) 1902–1911.
ing.html, or from the Cambridge Crystallographic Data
Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax:
(+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk.
Supplementary data associated with this article can be
[24] The solubility of water in EtOAc is ca. 3.3wt% at rt M. del Carmen
Grande, C.M. Marschoff, J. Chem. Eng. Data 50 (2005) 1324–1327.
[25] G.M. Sheldrick, Acta Crystallogr. Sect. A 46 (1990) 467–473.
[26] A.J.C. Wilson (Ed.), International Tables for Crystallography, vol. C,
Kluwer, Dordrecht, 1992.