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(E)-3-[2,5-Dioxo-3-(propan-2-yl-idene)pyrrolidin-1-yl]acrylic acid.

ABSTRACT: The title compound, C(10)H(11)NO(4), was extracted from a culture broth of Penicillium verruculosum YL-52. The mol-ecular structure is essentially planar, with an r.m.s. deviation of 0.01342?(2)?Å for the non-H atoms. In the crystal structure, adjacent mol-ecules are connected into a centrosymmetric dimer through a pair of O-H?O hydrogen bonds. The dimers are further extended into a chain by weak C-H?O hydrogen bonds.

SUBMITTER: Miao F

PROVIDER: S-EPMC2983691 | biostudies-other | 2010

REPOSITORIES: biostudies-other

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(E)-3-[2,5-Dioxo-3-(propan-2-yl-idene)pyrrolidin-1-yl]acrylic acid.

Miao Fang F Qin Bao-Fu BF Yang Li-Zhen LZ Yang Xin-Juan XJ Zhou Le L

Acta crystallographica. Section E, Structure reports online 20100213 Pt 3

The title compound, C(10)H(11)NO(4), was extracted from a culture broth of Penicillium verruculosum YL-52. The mol-ecular structure is essentially planar, with an r.m.s. deviation of 0.01342 (2) Å for the non-H atoms. In the crystal structure, adjacent mol-ecules are connected into a centrosymmetric dimer through a pair of O-H⋯O hydrogen bonds. The dimers are further extended into a chain by weak C-H⋯O hydrogen bonds. ...[more]

PMID: 21580390

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Synthesis, Anticonvulsant, and Antinociceptive Activity of New 3-(2-Chlorophenyl)- and 3-(3-Chlorophenyl)-2,5-dioxo-pyrrolidin-1-yl-acetamides.

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Project description:The title compound, C(10)H(12)FN(3)S, crystallizes in the same space group (P2(1)/c) as two polymorphic forms of 4-phenyl-1-(propan-2-yl-idene)thio-semicarbazone [Jian et al. (2005). Acta Cryst. E61, o653-o654; Venkatraman et al. (2005). Acta Cryst. E61, o3914-o3916]. The arrangement of mol-ecules relative to the twofold screw axes is similar to that in the crystal structure of the lower density polymorph. In the solid state, the mol-ecular conformation is stabilized by an intra-molecular N-H⋯N hydrogen bond. The mol-ecules form centrosymmetric R(2) (2)(8) dimers in the crystal through pairs of N-H⋯S hydrogen bonds.

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Project description:The configuration about each C=N bond in the title compound, C(22)H(20)N(4)O(3)S, is E. While to a first approximation the phenyl-hydrazin-1-yl-idene and benzohydrazide residues are coplanar, in part due to the presence of an intra-molecular N-H?N hydrogen bond, significant twists are evident in the orientations of the hydrazine [N-N-C-C torsion angle = -170.74?(11)°] and benzoyl benzene [N-C-C-C = -21.72?(18)°] rings. The sulfonyl benzene ring occupies a position almost normal to the rest of the mol-ecule [C-S-C-N = -92.28?(10)°]. Centrosymmetric aggregates mediated by pairs of hydrazide-sulfonyl N-H?O hydrogen bonds are the predominant packing motif in the crystal. These are connected into linear supra-molecular chains via C-H?O inter-actions which are, in turn, linked into layers in the ac plane via C-H?? inter-actions. Connections between layers along the b-axis direction are of the ?-? type and occur between centrosymmetrically related hydrazine-bound benzene rings [centroid-centroid separation = 3.7425?(9)?Å].

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Crystal structures of 1-(4-chloro-phen-yl)-4-(4-methyl-phen-yl)-2,5-dioxo-1,2,5,6,7,8-hexa-hydro-quinoline-3-carb-oxy-lic acid and 4-(4-meth-oxy-phen-yl)-1-(4-methyl-phen-yl)-2,5-dioxo-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbo-nitrile.

Project description:In the title compounds C23H21ClN2O3 [I, namely 1-(4-chloro-phen-yl)-4-(4-methyl-phen-yl)-3,8-dioxo-1,2,5,6,7,8-hexa-hydro-quine-3-carb-oxy-lic acid] and C24H22N2O3 [II, namely 4-(4-meth-oxy-phen-yl)-1-(4-methyl-phen-yl)-2,5-dioxo-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbo-nitrile], each of the cyclo-hexene and di-hydro-pyridine rings of the 1,2,5,6,7,8-hexa-hydro-quinoline moieties adopts a twisted-boat conformation. The asymmetric units of both compounds I and II consist of two independent mol-ecules (A and B). In II A, three carbon atoms of the cyclo-hexene ring are disordered over two sets of sites in a 0.670 (11):0.330 (11) occupancy ratio. In the crystal of I, mol-ecules are linked through classical N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif and with their mol-ecular planes parallel to the crystallographic (020) plane. Non-classical C-H⋯O hydrogen-bonding inter-actions connect the dimers, resulting in a three-dimensional network. In the crystal of II, mol-ecules are linked by C-H⋯N, C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional network.

| S-EPMC8025871 | biostudies-literature

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