Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 10 (October 2013)


organic compounds



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.


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[ doi:10.1107/S0108270113022981/fg3306Isup6.cml ]
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[ doi:10.1107/S0108270113022981/fg3306IIsup7.cml ]
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[ doi:10.1107/S0108270113022981/fg3306IIIsup8.cml ]
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[ doi:10.1107/S0108270113022981/fg3306IVsup9.cml ]
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