Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 3 (March 2013)

organic compounds

Acta Cryst. (2013). C69, 267-272    [ doi:10.1107/S0108270113002291 ]

An additional methyl­ene group driving the conformation and assembly of two aryl­sulfonamide para-alk­oxy­chalcone hybrids

M. R. C. de Castro, A. Q. Aragão, H. B. Napolitano, C. Noda-Perez and F. T. Martins

Abstract: The structures of two aryl­sulfonamide para-alk­oxy­chalcones, namely, N-{4-[(E)-3-(4-methoxy­phenyl)prop-2-en­oyl]phenyl}benzene­sulfon­amide, C22H19NO4S, (I), and N-{4-[(E)-3-(4-ethoxy­phenyl)prop-2-en­oyl]phenyl}benzene­sulfon­amide, C23H21NO4S, (II), reveal the effect of the inclusion of one -CH2- group between the CH3 branch and the alk­oxy O atom on the conformation and crystal structure. Although the mol­ecular conformations and one-dimensional chain motifs are the same in both structures, their crystallographic symmetry, number of independent mol­ecules and crystal packing are different. The crystal packing of (I) is stabilized by weak C-H...[pi] and [pi]-[pi] inter­actions, while only C-H...[pi] contacts occur in the structure of (II). The role of the additional methyl­ene group in the crystal packing can also be seen in the fact that the alk­oxy O atom is an acceptor in non­classical hydrogen bonds only in the para-eth­oxy analogue, (II). The remarkable similarity between the crystal packing features of (I) and (II) lies in the formation of N-H...O hydrogen-bonded ribbons, a synthon commonly found in related compounds.

Formula: C22H19NO4S and C23H21NO4S

hkldisplay filedownload file

Structure factor file (CIF format) (401.5 kbytes)
[ doi:10.1107/S0108270113002291/uk3058Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (200.9 kbytes)
[ doi:10.1107/S0108270113002291/uk3058IIsup3.hkl ]
Contains datablock II


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