3-(Phenylcarbamoyl)acrylic acid

In the title compound, C10H9NO3, the dihedral angle between the phenyl ring and the amide group is 10.8 (2)°. The C=O and O—H bonds of the carboxyl group adopt an anti orientation and an intramolecular O—H⋯O hydrogen bond closes an S(7) ring. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(7) chains propagating in [101]. The packing is consolidated by C—H⋯O interactions, generating sheets aligned at an angle of ca 60° with the bc plane.

In the title compound, C 10 H 9 NO 3 , the dihedral angle between the phenyl ring and the amide group is 10.8 (2) . The C=O and O-H bonds of the carboxyl group adopt an anti orientation and an intramolecular O-HÁ Á ÁO hydrogen bond closes an S(7) ring. In the crystal, N-HÁ Á ÁO hydrogen bonds link the molecules into C(7) chains propagating in [101]. The packing is consolidated by C-HÁ Á ÁO interactions, generating sheets alligned at an angle of ca 60 with the bc plane
The single-crystal of the title compound ( Fig.1) with the formula C 10 H 9 NO 3 was obtained by recrystallization of 3phenylcarbamoyl-acrylic acid and 2-methylquinoline from a methanol solution. However the 2-methylquinoline molecules do not appear in the title compound. X-ray diffraction analysis indicated that the asymmetric unit of the structure contains one molecule. The conformations of the amide oxygen and the carbonyl oxygen of the acid segments are anti to each other and the amide oxygen is anti to the H atom on the olefinic group, while the carbonyl oxygen of the acid is syn to the CH at the olefinic group. Thus there existed intramolecular O-H···O hydrogen bond producing a S 1 1 (7) ring.
The dihedral angle between the phenyl ring and the amide group in the molecule is 10.8 (2)°.
Two adjacent 3-phenylcarbamoyl-acrylic acids were joined together via the N-H···O, and CH-O interactions to form a dimer. Both carboxylic acids in the dimer were almost perpendicular with each other. In the dimer there are hydrogenbonded ring motifs with descriptors of R 2 1 (6), and R 2 2 (8). The two ring motifs were fused together by the N-H···O hydrogen bond. The neighboring carboxylic dimers were linked together through the CH-O associations between the benzene CH and the carbonyl group with C-O distance of 3.389 Å to form one-dimensional chain. The one-dimensional chains were combined together by the interchain CH-O, and N-H···O interactions to form two-dimensional sheet extending at the direction that made a dihedral angle of ca 60° with the bc plane (Fig. 2). Two two-dimensional sheets were further held together by the intersheet C-π interactions with C···C g distance of 3.369 Å to generate two-dimensional double sheet structure.

Experimental
Crystals of 3-phenylcarbamoyl-acrylic acid were formed by slow evaporation of its methanol solution at room temperature. 3-phenylcarbamoyl-acrylic acid (19.1 mg, 0.10 mmol) was dissolved in 4 ml of methanol, and 2-methylquinoline (14.3 mg, 0.1 mmol) was added to the methanol solution. The solution was then filtered into a test tube and left standing at room temperature. After about one week colorless blocks crystals were obtained.

Refinement
H atoms bonded to O, and N atoms were located in a difference Fourier map and refined isotropically.
Other H atoms were positioned geometrically with C-H = 0.93 Å for aromatic, and constrained to ride on their parent atoms with U iso (H) = 1.2Ueq(C).

Figure 1
The structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.

Figure 2
Two-dimensional sheet structure formed through hydrogen bonds. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.