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Ethyl (E)-2-cyano-3-(4-methyl-phen-yl)acrylate: a second monoclinic polymorph.

ABSTRACT: The title compound, C13H13NO2, was previously described in space group P21/c by He et al. [Acta Cryst. (1993), C49, 2000-2002]. The ethyl group is disordered over two sets of sites in a 0.615?(10):0.385?(10) ratio. The C-O-C-C torsion angles containing the ethyl group are -111.6?(10) and 177.9?(7)°, while in the previously reported polymorph, the torsion angle is -167.3?(2)°. The molecules pack to form a three-dimensional structure in the ABAB style along the c-axis direction in the title compound, but parallel to the a-axis direction in the reported polymorph.

SUBMITTER: Chen QY

PROVIDER: S-EPMC3648277 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Ethyl (E)-2-cyano-3-(4-methyl-phen-yl)acrylate: a second monoclinic polymorph.

Chen Qi-Yu QY Ke Wen-Dong WD Kong Lin L

Acta crystallographica. Section E, Structure reports online 20130417 Pt 5

The title compound, C13H13NO2, was previously described in space group P21/c by He et al. [Acta Cryst. (1993), C49, 2000-2002]. The ethyl group is disordered over two sets of sites in a 0.615 (10):0.385 (10) ratio. The C-O-C-C torsion angles containing the ethyl group are -111.6 (10) and 177.9 (7)°, while in the previously reported polymorph, the torsion angle is -167.3 (2)°. The molecules pack to form a three-dimensional structure in the ABAB style along the c-axis direction in the title compou ...[more]

PMID: 23723897

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Synthesis, characterization, crystal structure and supra-molecularity of ethyl (<i>E</i>)-2-cyano-3-(3-methyl-thio-phen-2-yl)acrylate and a new polymorph of ethyl (<i>E</i>)-2-cyano-3-(thio-phen-2-yl)acrylate.

Project description:The synthesis, crystal structure and structural motif of two thio-phene-based cyano-acrylate derivatives, namely, ethyl (E)-2-cyano-3-(3-methyl-thio-phen-2-yl)acrylate (1), C11H11NO2S, and ethyl (E)-2-cyano-3-(thio-phen-2-yl)acrylate (2), C10H9NO2S, are reported. Derivative 1 crystallized with two independent molecules in the asymmetric unit, and derivative 2 represents a new monoclinic (C2/m) polymorph. The mol-ecular conformations of 1 and the two polymorphs of 2 are very similar, as all non-H atoms are planar except for the methyl of the ethyl groups. The inter-molecular inter-actions and crystal packing of 1 and 2 are described and compared with that of the reported monoclinic (C2/m) polymorph of derivative 2 [Castro Agudelo et al. (2017 ▸). Acta Cryst. E73, 1287-1289].

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(E)-Ethyl 3-(3-bromo-phen-yl)-2-cyano-acrylate.

Project description:The title mol-ecule, C(12)H(10)BrNO(2), adopts an E configuration with respect to the C=C bond of the acrylate unit. In the crystal structure, mol-ecules are connected by a pair of inter-molecular C-H?O hydrogen bonds, forming a centrosymmetric dimer.

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Ethyl (2E)-2-cyano-3-(4-meth-oxy-phen-yl)acrylate.

Project description:In the title compound, C13H13NO3, the conformation across the C=C bond is synperiplanar, the torsion angle of the segment C(ring)-C=C-C(N) being 3.2?(5)°. In the crystal, mol-ecules are linked into inversion dimers, arranged in a zigzag pattern, through two C-H?O inter-actions generating R 2 (2)(10) and R 2 (2)(14) motifs. These dimers are arranged in a zigzag pattern in the crystal structure. The mol-ecules are further linked along the c axis through weak C-H?? inter-actions, and weak ??? inter-actions [centroid-centroid separation = 3.9986?(17)?Å] are also observed.

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A second monoclinic polymorph of (E)-phen-yl(pyridin-2-yl)methanone oxime.

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N-(2-Formyl-phen-yl)-4-toluene-sulfonamide: a second monoclinic polymorph.

Project description:The title compound, C(14)H(13)NO(3)S, (I), is a second monoclinic polymorph. The original polymorph, (II), was reported by Mahía et al. [Acta Cryst. (1999), C55, 2158-2160]. Polymorph (II) crystalllized in the space group P2(1)/c (Z = 4), whereas the title polymorph (I) occurs in the space group P2(1)/n (Z = 4). The dihedral angle between the two aromatic rings is 75.9 (1)° in (I) compared to 81.9 (1)° for (II). In both polymorphs, two S(6) rings are generated by intra-molecular N-H⋯O and C-H⋯O hydrogen bonds, resulting in similar mol-ecular geometries. However, the two polymorphs differ concerning their crystal packing. In (I), mol-ecules are linked into C(8) zigzag chains along the b axis by C-H⋯O hydrogen bonds, whereas in (II) mol-ecules are linked by C-H⋯O hydrogen bonds, forming C(7) chains along the b axis. The title polymorph is further stabilized by inter-molecular C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.814 (1) Å]. These inter-actions are not evident in polymorph (II).

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(E)-Ethyl 2-cyano-3-[5-nitro-2-(pyrrolidin-1-yl)phen-yl]acrylate.

Project description:The title compound, C(16)H(17)N(3)O(4), was prepared by the reaction of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde and ethyl cyano-acetate. The mol-ecular structure adopts an E conformation with respect to the C=C double bond. The five-membered ring has a half-chair conformation, with puckering parameters Q(2)= 0.399 (2) Å and ϕ = 93.1 (3)°. In the crystal, inversion dimers , linked by pairs of C-H⋯O inter-actions, are further connected through C-H⋯N hydrogen bonds. Weak slipped π-π inter-actions occur between symmetry-related benzene rings [centroid-centroid distance = 3.785 (1)Å].

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A second monoclinic polymorph of N-(2,4-dinitro-phen-yl)-2,4-dinitro-aniline.

Project description:The title compound, C(12)H(7)N(5)O(8), was previously described in space group P2(1)/n with Z = 4 [Wu et al. (2007 ▶). Acta Cryst. E63, o4194]. The current monoclinic P2(1)/c polymorph was obtained from a mixed solution of dichloro-methane and hexane. The dihedral angle between the benzene rings is 44.16 (5)°, smaller than in the previously reported polymorph [56.3 (2)°]. As a result of the steric hinderance of the nitro groups, hydrogen bonding is limited intramolecularly. The dihedral angles between the phenyl rings and their attached nitro groups are 18.97 (6) and 17.71 (5)° at the 2-position, and 18.52 (6) and 32.41 (6)° at the 4-position.

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(E)-Ethyl 2-cyano-3-[4-(4,5-diphenyl-1H-imidazol-2-yl)phen-yl]acrylate dihydrate.

Project description:In the title compound, C(27)H(21)N(3)O(2)·2H(2)O, the three benzene rings attached to the heterocyclic imidazole ring are not coplanar with the latter, making dihedral angles of 14.8 (2), 31.4 (2), and 37.5 (2)°, respectively, for the benzene ring planes in the 2-, 4- and 5-positions. In the crystal, there are two water mol-ecules which serve as connectors between the acrylate mol-ecules and stabilize the structure via N-H⋯O, O-H⋯N, C-H⋯O and O-H⋯O hydrogen bonding.

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(Z)-Ethyl 3-(4-chloro-benzamido)-2-cyano-3-(4-fluoro-phen-yl)acrylate.

Project description:The title compound, C(19)H(14)ClFN(2)O(3), was prepared by the reaction of ethyl (Z)-3-amino-2-cyano-3-(4-fluoro-phen-yl)acrylate and 4-chloro-benzoyl chloride. The dihedral angle between the chloro-benzene and fluoro-benzene rings is 66.18 (19)°. In addition to an intra-molecular N-H⋯O hydrogen bond, there are inter-molecular C-H⋯O and C-H⋯N hydrogen bonding inter-actions, which stabilize the crystal structure.

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(Z)-Ethyl 3-(4-chloro-phen-yl)-2-cyano-3-(2,6-difluoro-benzamido)acrylate.

Project description:The title compound, C(19)H(13)ClF(2)N(2)O(3), was prepared by the reaction of (Z)-ethyl 3-amino-3-(4-chloro-phen-yl)-2-cyano-acrylate and 2,6-difluoro-benzoyl chloride. The dihedral angle between the chloro-benzene and fluoro-benzene rings is 37.0 (1)°. The ethyl group is disordered over two positions [occupancies = 0.52 (2):0.48 (2)]. In addition to intra-molecular N-H⋯O and N-H⋯F hydrogen bonds, the crystal packing shows the mol-ecules to be connected by inter-molecular C-H⋯O and C-H⋯N hydrogen bonds.

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