Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 10 (October 2013)


organic compounds



fg3306 scheme

Acta Cryst. (2013). C69, 1157-1163    [ doi:10.1107/S0108270113022981 ]

Four related diethyl [(arylamino)(4-ethynylphenyl)methyl]phosphonates

A. Ouahrouch, J. Krim, M. Taourirte, H. B. Lazrek, J. W. Engels and J. W. Bats

Abstract: Crystal structures are reported for four related diethyl [(arylamino)(4-ethynylphenyl)lmethyl]phosphonate derivatives, namely diethyl [(4-bromoanilino)(4-ethynylphenyl)methyl]phosphonate, C19H21BrNO3P, (I), diethyl ((4-chloro-2-methylanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C23H31ClNO3PSi, (II), diethyl ((4-fluoroanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C22H29FNO3PSi, (III), and diethyl [(4-ethynylphenyl)(naphthalen-2-ylamino)methyl]phosphonate, C23H24NO3P, (IV). The conformation of the anilinobenzyl group is very similar in all four compounds. The P-C bond has an approximately staggered conformation, with the aniline and ethynylphenyl groups in gauche positions with respect to the P=O double bond. The two six-membered rings are almost perpendicular. The sums of the valence angles about the N atoms vary from 344 (2) to 351 (2)°. In the crystal structures, molecules of (I), (III) and (IV) are arranged as centrosymmetric or pseudocentrosymmetric dimers connected by two N-H...O=P hydrogen bonds. The molecules of (II) are arranged as centrosymmetric dimers connected by Cmethyl-H...O=P hydrogen bonds. The N-H bond of (II) is not involved in hydrogen bonding.

Formula: C19H21BrNO3P, C23H31ClNO3PSi, C22H29FNO3PSi and C23H24NO3P

Keywords: crystal structure; diethyl [(arylamino)(4-ethynylphenyl)methyl]phosphonates.


hkldisplay filedownload file

Structure factor file (CIF format) (233.3 kbytes)
[ doi:10.1107/S0108270113022981/fg3306Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (246.0 kbytes)
[ doi:10.1107/S0108270113022981/fg3306IIsup3.hkl ]
Contains datablock II


hkldisplay filedownload file

Structure factor file (CIF format) (234.2 kbytes)
[ doi:10.1107/S0108270113022981/fg3306IIIsup4.hkl ]
Contains datablock III


hkldisplay filedownload file

Structure factor file (CIF format) (406.4 kbytes)
[ doi:10.1107/S0108270113022981/fg3306IVsup5.hkl ]
Contains datablock IV


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