Crystal structure of 4-[(2-methoxyphenyl)carbamoyl]butanoic acid, C₁₂H₁₅NO₄

Abstract

C12H15NO4, triclinic, P1̄ (no. 2), a = 7.4325(3) Å, b = 7.5171(3) Å, c = 23.7377(9) Å, α = 87.780(3)°, β = 89.105(3)°, γ = 61.299(4)°, V = 1162.42(9) Å3, Z = 4, Rgt(F) = 0.0566, wRref(F2) = 0.1652, T = 100(2) K.

Crystal structure of 4-[(3,5-dichlorophenyl)carbamoyl]butanoic acid, C11H11Cl2NO3

“…Complementing the twist about the C3-C4 bond, is a second twist in the molecule involving the aryl group as seen in the C5-N1-C6-C7 torsion angle of −133.95(18)°. The highly twisted conformation for (I) matches that seen in (II) [5] and one of two independent molecules of (IV) [7]. Decidedly more planar conformations are noted for the other molecules [6,7].…”

“…The C-bound H atoms were geometrically placed (C-H = 0.93-0.97 Å) and refined as riding with U iso (H) = 1. [7], hereafter (III) and (IV), respectively. An emerging interesting feature of these structures is the conformational flexibility in the side-chain.…”

Crystal structure of 4-[(3-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4

“…The title 4-[(aryl)carbamoyl]butanoic acid derivative, ArN(H)C(=O)(CH 2 ) 3 C(=O)OH, with Ar = 3-methoxyphenyl, is an isomer of the recently described Ar = 2-methoxyphenyl species [5], the structure of which complemented a rather small number of related species, i.e. with Ar = 4-((methylsulfonyl)amino)-3-phenoxyphenyl [6], Ar = 3,5dichlorophenyl [7] and Ar = 4-methoxy-2-nitrophenyl [8].…”

“…C1-O1 = 1.316 2 14°] torsion angles. The highly twisted conformation noted for (I) can be compared with the two independent molecules comprising the asymmetric unit in the crystal of the isomeric Ar = 2-methoxyphenyl analogue [5], one of which is also twisted and the other which has an all-trans (planar) carbon backbone. The conformational flexibility of these molecules is also apparent in the derivative with Ar = 3,5-dichlorophenyl [7] where a twisted conformation is observed but, when Ar = 4methoxy-2-nitrophenyl [8], an all-trans conformation is noted.…”

4-[(2,4-Dichlorophenyl)carbamoyl]butanoic Acid

“…Hybrid glutaric acid-amides molecules of the general formula ArN(H)C(=O)(CH 2 ) 3 C v(=O)OH have attracted recent interest in terms of biological activity, that is, as anti-cancer and anti-leishmanial agents [1], their organotin derivatives, for anti-cancer potential [2], and X-ray crystallographic structural studies [3][4][5][6][7]. The Ar = 2,4-dichlorophenyl derivative (1), Figure 1, has been reported previously but without spectroscopic and crystallographic characterization [8].…”