Crystal structure of 2-benzyl-3-hydroxyisoindolin-1-one, C15H13NO2

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C15H13NO2, monoclinic, P121/c1 (no. 14), a = 12.987(2) A, b = 7.691(1) A, c = 12.083(3) A, 3 = 96.970(4)°, V = 1198.0 A, Z = 4, Rgt(F) = 0.047, wRref(F) = 0.127, T = 153 K. Source of material The title compoundwas obtained from a two-step reaction. A free radical bromination was used to attach a bromide at the 4-H atom of phthalide, forming 3-bromophthalide (see CIF for details). 3Bromophthalide was reactedwith benzylamine in the presence of base: To a 100 mL round bottom flask with a magnetic stirbar, 3bromophthalide (2.24 g, 10.5mmol) was dissolved in acetonitrile (20mL). After stirring for 5min, diisopropylethylamine (3.16mL, 17.5 mmol) and benzylamine (1.26 mL, 11.4 mmol) were added. The reactionmixture was stirred at room temperature for 4 h. The solvent was then removed under conditions of reduced pressure. The crude residue was purified by silica gel chromatography, using hexane and ethyl acetate gradient. The product portion was collected and evaporated under reduced pressure (55 %). Yellow crystals were obtained by recrystallization from methanol solution. HNMR, CNMR, IR andMSdata are also available in the CIF. Discussion The title compound is the result of an unexpected ring-closing reaction, the analogous amide-aldehydewas the expected structure. TheN1,C10C8atoms of the fused rings are essentially co-planar with themaximum deviation from their least-squares plane being 0.017(1)A for theN1 atom; the carbonyl-O1 and benzyl-C9 atoms lying 0.020(1)A and –0.204(1)A out of this plane. The hydroxyl group lies to the opposite side of the fused ring system to that occupied by the benzyl residue. The molecule is bent at the benzyl-C9 atom as manifested in the dihedral angle of 84.38(6)° between the planes through the fused ring systemand the phenyl ring. The molecules are connected into a supramolecular chain along the [001] direction via O–H···O hydrogen bonds formed between the hydroxyl and carbonyl groups. The parameters associated with this interaction are d(O2–H···O1) = 1.87 A, d(O2···O1) = 2.707(2) A with an angle at H of 176° for i: x,1/2–y,–1/2+z. Z. Kristallogr. NCS 223 (2008) 25-26 / DOI 10.1524/ncrs.2008.0012 25 © by Oldenbourg Wissenschaftsverlag, Munchen Crystal: yellow prism, size 0.20 × 0.20 × 0.35 mm Wavelength: Mo K4 radiation (0.71070 A) *: 0.89 cm−1 Diffractometer, scan mode: Rigaku AFC12 & SATURN724, 6 2%max: 53.0° N(hkl)measured, N(hkl)unique: 8373, 2477 Criterion for Iobs, N(hkl)gt: Iobs > 2 #(Iobs), 2348 N(param)refined: 166 Programs: teXsan [1], SIR-92 [2], SHELXL-97 [3], ORTEP-II [4] Table 1. Data collection and handling.