2-(2-Hy­droxy­phen­yl)-3,4-dihydro­iso­quinolin-1(2H)-one

Jian Yang; Yanni Ma; Meng Pan; Fangjun Cao; Le Zhou

doi:10.1107/S160053681103710X

. 2011 Sep 30;67(Pt 10):o2721. doi: 10.1107/S160053681103710X

2-(2-Hydroxyphenyl)-3,4-dihydroisoquinolin-1(2H)-one

Jian Yang ^a, Yanni Ma ^a, Meng Pan ^a, Fangjun Cao ^a, Le Zhou ^a,^*

PMCID: PMC3201540 PMID: 22065631

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₁₅H₁₃NO₂, in both the six-membered dihydropyridine rings adopt a half-chair conformation. The two benzene rings make dihedral angles of 43.66 (10) and 62.22 (10)° in the two molecules. In the crystal, the two independent molecules are linked alternately by intermolecular O—H⋯O hydrogen bonds, forming a zigzag chain along the c axis. Furthermore, intermolecular C—H⋯π interactions link the chains into a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Shaw & Zhang (2008 ▶). For the bioactivity of tetrahydroisoquinoline derivatives, see: Kamal et al. (2011 ▶); Liu et al. (2009 ▶); Vrba et al. (2009 ▶); Abe et al. (2005 ▶); Adhami et al. (2004 ▶); Storch et al. (2002 ▶).

Experimental

Crystal data

C₁₅H₁₃NO₂
M _r = 239.26
Monoclinic,
a = 21.350 (3) Å
b = 11.0670 (14) Å
c = 21.064 (3) Å
β = 100.227 (2)°
V = 4897.9 (11) Å³
Z = 16
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.50 × 0.35 × 0.34 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.958, T _max = 0.971
17755 measured reflections
4559 independent reflections
2998 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.120
S = 1.01
4559 reflections
326 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103710X/is2770sup1.cif

e-67-o2721-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103710X/is2770Isup2.hkl

e-67-o2721-Isup2.hkl^{(223.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681103710X/is2770Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.82	1.84	2.6388 (18)	166
O4—H4A⋯O1	0.82	1.85	2.6668 (17)	175
C7—H7B⋯Cg2ⁱⁱ	0.97	2.92	3.770 (2)	147
C19—H19⋯Cg2ⁱⁱⁱ	0.93	2.78	3.518 (3)	137
C23—H23A⋯Cg3^iv	0.97	2.87	3.771 (2)	155

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (NNSF; Nos. 30771454, 31000865).

supplementary crystallographic information

Comment

The tetrahydroisoquinoline derivatives have recently attracted a great deal of attention because of their outstanding bioactivity, such as neurotoxicity (Abe et al., 2005; Storch et al., 2002), antitumor activity (Vrba et al., 2009; Adhami et al., 2004), antimicrobial activity (Kamal et al., 2011; Liu et al., 2009), and so on. With the interests in the synthesis of tetrahydroisoquinoline derivatives with bioactivity, we herein report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound include two independent molecules (Fig. 1), each is built up from one 3,4-dihydroisoquinolin-1(2H)-one fragment connected to one 2-hydroxybenzene ring through the C—N bond. Benzene rings C1—C6 and C10—C15 are inclined with respect to one another with a dihedral angle of 43.66 (10) °, and benzene C16—C21 and C25—C30 with a dihedral angle of 62.22 (10) °. The conformation of the six-membered heterocycle of 3,4-dihydroisoquinolin-1(2H)-one fragment is analyzed with respect to the plane formed by C1/C6/C7/C9 and the corresponding deviations of the atoms C8 and N1 are 0.852 and 0.339 Å, respectively. Meanwhile, the corresponding deviations of the atoms C23 and N2 from the plane formed by C16/C21/C22/C24 are 0.761 and 0.289 Å, respectively.

In the crystal structure, the molecules are linked by intermolecular O—H···O hydrogen bonds (Table 1) into a chain along the c axis. These chains are further connected by C—H···π interactions (C7—H7B···Cg2 and C23—H23A···Cg3; Table 1) into a sheet, where Cg2 is the centroid of the benzene C1—C6 ring and Cg3 is of the benzene C10—C15 ring. Furthermore, C19—H19···Cg2 interaction connects the sheets into three-dimension framework (Fig. 2).

Experimental

The title compound was synthesized according to the literature procedure (Shaw & Zhang, 2008). An NaOH solution (0.1 mol/L, 10 ml) was added to the solution of 2-(2-hydroxyphenyl)-3,4-dihydroisoquinolinum bromide (304 mg, 1 mmol) in ethanol (10 ml) dropwise under stirring. After 24 h, the mixture was extracted by chloroform (30 ml), dried over anhydrous Na₂SO₄ and evaporated under reduced pressure. Further purification by silicagel column chromatography (petroleum ether / ethyl acetate = 5:1) and recrystallization gave 85 mg the title compound (yield 36%; m.p. 433–434 K).