N-[2-(Acetamido)ethyl]-2-hydroxybenzamide

In the title molecule, C11H14N2O3, an intramolecular O—H⋯O hydrogen bond closes an almost planar [maximum deviation = 0.022 (13) Å] six-membered ring and enforces the cis conformation of the keto group with respect to the hydroxy substituent. In the crystal, intermolecular N—H⋯O hydrogen bonds link the moleclues into ribbons extended along [10]. Weak intermolecular C—H⋯O interactions further consolidate the crystal packing.

In the title molecule, C 11 H 14 N 2 O 3 , an intramolecular O-HÁ Á ÁO hydrogen bond closes an almost planar [maximum deviation = 0.022 (13) Å ] six-membered ring and enforces the cis conformation of the keto group with respect to the hydroxy substituent. In the crystal, intermolecular N-HÁ Á ÁO hydrogen bonds link the moleclues into ribbons extended along [110]. Weak intermolecular C-HÁ Á ÁO interactions further consolidate the crystal packing.
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97. If only one RNA can be chosen from many RNAs in cells and selectively cleaved at desired site, it opens the way to new RNA science (e.g. regulation of expression of a specific gene, advanced therapy, RNA manipulation) (Kuzuya et al., 2006).
During the past decade, mimics for RNA-cleaving enzymes, ribonucleases, have received special attention (Nüttymäki et al., 2006). The first artificial nucleases capable of cleaving RNA oligonucleotides in a selective manner were DNA conjugates of lanthanide(III) ion complexes (Komiyama et al., 1999;Franklin, 2001;Morrow et al., 2004). The title compound (I, Scheme 1) was isolated during efforts to prepare new synthetic ribonuclease precursors as part of our research program involving the study of the nonselective and selective hydrolysis of RNA by lanthanide complexes.
The conformation of the CNCCNCC chain in (I) is tg + tgt (t -trans, g -gauche), as can be seen from the values of the torsion angles. Intramolecular hydrogen bond between hydroxy group and O7 oxygen atom causes closing of the sixmembered nearly planar (within 0.022 (13) Å) ring ( Fig. 1). This bond is strong and causes the changes in the geometry of involved fragments: lengthening of both O-H (1.11 (4) Å) and C=O (1.255 (3) Å) bonds. This ring is almost coplanar with the phenyl ring plane, the dihedral angle between the two planes is 1.6 (9)°. In the Cambridge Structural Database which are close to 180° for the former and close to 0° for the latter possibility (cf. Fig. 2). The overall conformation of the molecule can be described as two almost planar (within 0.022 (2) Å) and nearly parallel (the dihedral angle is 5.65 (16)°) fragments C1···C9 and C10···C13.
In the crystal structure, the variety of hydrogen bonds connects the molecules of I into the hydrogen-bonded chains of molecules (cf. Table 1). The pairs of almost linear N11-H11···O7(1 -x,2 -y,1 -z) and N8-H8···O12(2 -x,1 -y,1 -z) hydrogen bonds join the molecules in centrosymmetric dimers, the graph set connected with these interactions are R 2 2 (14). Each of these bonds is accompanied by secondary however still relatively short and directional C-H···O interactions ( Table   1). As can be seen in Fig. 3 these bonds in general join two different "storeys" of the molecules in alternating manner. Therefore these interactions create the double ribbons of molecules which expand approximately along [-110] direction.
The interactions between these motifs are only very week.
The rest H atoms were found in the diffrence Fourier maps and isotropically refined.     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 Rfactors(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.