Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 2 (February 2014)

organic compounds

sf3215 scheme

Acta Cryst. (2014). C70, 210-215    [ doi:10.1107/S2053229613034839 ]

Comparison of N-(3,4,5-tri­meth­oxy­benzyl­idene)naphthalen-1-amine and its reduction product N-(3,4,5-tri­meth­oxy­benzyl)naphthalen-1-amine

A. Garay, R. Abonía, J. Cobo and C. Glidewell

Abstract: The mol­ecules in (E)-N-(3,4,5-tri­meth­oxy­benzyl­idene)naph­thalen-1-amine, C20H19NO3, (I), and its reduction product N-(3,4,5-tri­meth­oxy­benzyl)naphthalen-1-amine, C20H21NO3, (II), are both conformationally chiral, but (I) crystallizes in a centrosymmetric space group, while (II) crystallizes with just one conformational enantio­mer in each crystal. A combination of two C-H...O hydrogen bonds links the mol­ecules of (I) into sheets containing a single type of R66(44) ring, and these sheets are linked into a continuous three-dimensional array by a single [pi]-[pi] stacking inter­action. The mol­ecules of (II) are linked into complex sheets by a combination of N-H...O, C-H...O and C-H...[pi](arene) hydrogen bonds.

CCDC references: 979036 and 979037

Formula: C20H19NO3 and C20H21NO3

Keywords: crystal structure; supra­molecular structure; hydrogen bonding.

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Chemical Markup Language (CML) file (6.6 kbytes)
[ doi:10.1107/S2053229613034839/sf3215Isup4.cml ]
Supplementary material

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Chemical Markup Language (CML) file (6.7 kbytes)
[ doi:10.1107/S2053229613034839/sf3215IIsup5.cml ]
Supplementary material


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