Abstract
The structures of two diastereomers ((1R,2R) and (1R,2S)) of the title compound have been determined. The molecular conformation of the (1R,2R) isomer is heavily influenced by strong intramolecular hydrogen bonding between the secondary and tertiary amine groups (N(1)…N(2) 2.629(8) Å; N(4)…N(5) 2.628(8) Å). In the (1R,2S) isomer no intramolecular interaction is observed, but somewhat weaker intermolecular hydrogen bonding does occur between the secondary amine and the carbonyl group of a neighboring molecule (N(1)…O(1) 2.960(6) Å) related by a 21 screw operation along thea-axis (x1/40). No close intermolecular contacts are observed for the (1R,2R) isomer. Crystal data for (1R,2R); monoclinic,P21 (No. 4),a=18.588(5),b=16.743(4),c=6.062(1) Å, β=97.26(2)o,V=1871.5(8) A3, Z=4,D cale=1.16 g/cm3. Crystal data for (1R,2S): orthorhombic,P212121 (No. 19),a=8.008(2),b=9.985(3),c=23.458(5)Å,V=1875.8(6) Å3, Z=4,D cale=1.15 g/cm3.
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(a)Jones, D.S.; Srinivasan, A.; Kasina, S.; Fritzberg, A.R.; Wilkening, D.W.J. Org. Chem. 1988,54, 1940, and references cited therein. (b) DeRiemer. L.H.; Meares, C.F.; Goodwin, D.A.; Diamanti, C.I.J. Label. Compd. Radiopharm. 1981,18, 1517
Lehn, J.-M.Acc. Chem. Res. 1978,11, 49. and references cited therein.
Popter, A.E. InComprehensive Heterocyclic Chemistry; Katritzky, A.R.; Rees, C.W., Eds.: Pergamon Press; Oxford, 1984; Vol. 3, p 179.
Kasina, K.; Fritzberg, A.R.; Johnson, D.L.; Eshima, D.J.J. Med. Chem. 1986,29, 1933.
(a)Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y.J. Am. Chem. Soc. 1984,106, 5754. (b) Peyronel, J.-F.; Samuel, O.; Fiaud, J.C.J. Org. Chem. 1987,52, 5320, and references cited therein.
(a) Corey, E.J.; Imwinkelried, R.; Pikul, S.; Xiang, Y.B.J. Am. Chem. Soc. 1989,111, 5493. (b) Corey, E.J.; Yu. C.-M.; Kim, S.S.Ibid J. Am. Chem. Soc. 1989,111, 5495. (c) Corey, E.J.; Yu. C.-M.; Lee, D.-H.Ibid. J. Am. Chem. Soc. 1990,112, 878.
Corey, E.J.; Kim, S.S.J. Am. Chem. Soc. 1990,112, 4976.
Gruseck, U.; Heuschmann, M.Tetrahedron Lett. 1987,28, 2681.
(a) Onuma, K.; Ito, T.; Nakamura, A.Bull. Chem. Soc. Jpn. 1980,25, 2012. (b) Fiorini, M.; Giongo, G.M.J. Mol. Catalysis 1979,5, 303. (c) Zhang, W.; Loebach, J.L.; Wilson, S.R.; Jacobensen, E.N.J. Am. Chem. Soc. 1990,112, 2801. (d) Corey, E.J.; Jardine, P.D.; Virgil, S.; Yuen, P.W.; Connell, R.D.J. Am. Chem. Soc. 1989,111, 9243, (e) Tokles, M.; Snyder, J.K.Tetrahedron Lett. 1986,27, 3951.
Dieter, R.K.; Lagu, B.; Deo, N.; Dieter, J.W.Tetrahedron Lett. 1990,31, 4105.
Dieter, R.K.; Deo, N.; Lagu, B.; Dieter, J.W.J. Org. Chem. 1992,57, 1963.
Jackman, L.M.; Sternhall, S.Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, 2nd ed., Pergamon Press Ltd London, 1969; Chapter 4–2. pp 283–284.
Dieter, R.K.; Lagu B.; Dieter, J.W.; Deo. N.; Pennington, W.T.Synlett. 1990, 109.
Sheldrick, G.M.SHELXTL-Plus, Version 4.2. Structure Determination Sofware Programs; Siemens Analytical X-ray Instruments Inc., Madison, WI, 1990.
Cromer, D.T.; Waber, J.T.International Tables for X-ray Crystallography, Vol. IV, Table 2.2B; Birmingham: Kynoch Press, 1974.
Cromer, D.T.International Tables for X-ray Crystallography, Vol. IV, Table 2.3.1. Birmingham; Kynoch Press, 1974.
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Deo, N., Dieter, R.K., Lagu, B. et al. Two diastereomers of 2-[[β-(N-phenylamino)-α-methylphenethyl]-methylamino]-N,N-dimethylacetamide. J Chem Crystallogr 27, 689–694 (1997). https://doi.org/10.1007/BF02576547
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DOI: https://doi.org/10.1007/BF02576547