4-[(2-Hy­droxy­naphthalen-1-yl)(morpholin-4-yl)meth­yl]benzonitrile

Xin-Yuan Chen; Min-Min Zhao; Xu Qian; Shao-Gang Hou

doi:10.1107/S160053681104997X

. 2011 Nov 30;67(Pt 12):o3484. doi: 10.1107/S160053681104997X

4-[(2-Hydroxynaphthalen-1-yl)(morpholin-4-yl)methyl]benzonitrile

Xin-Yuan Chen ^a,^*, Min-Min Zhao ^a, Xu Qian ^a, Shao-Gang Hou ^a

PMCID: PMC3239108 PMID: 22199956

Abstract

The title compound, C₂₂H₂₀N₂O₂, was synthesized via a multicomponent reaction using naphthalen-2-ol, morpholine and 4-formylbenzonitrile. The dihedral angle between the naphthalene ring system and the benzene ring is 81.25 (10)°. The morpholine ring adopts a chair conformation. The molecular conformation is stabilized by intramolecular O—H⋯N and C—H⋯O hydrogen bonds. In the crystal, intermolecular C—H⋯N hydrogen bonds link molecules into helical chains running parallel to the c axis.

Related literature

For background to multi-component reactions, see: Devi & Bhuyan (2004 ▶); Domling & Ugi (2000 ▶). Hulme & Gore (2003 ▶); Ugi (1962 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₂H₂₀N₂O₂
M _r = 344.40
Trigonal,
a = 18.294 (3) Å
c = 28.738 (6) Å
V = 8329 (4) Å³
Z = 18
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.20 × 0.15 × 0.10 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.910, T _max = 1.000
24077 measured reflections
3326 independent reflections
1786 reflections with I > 2σ(I)
R _int = 0.138

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.210
S = 1.03
3326 reflections
235 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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) I, global. DOI: 10.1107/S160053681104997X/rz2668sup1.cif

e-67-o3484-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104997X/rz2668Isup2.hkl

e-67-o3484-Isup2.hkl^{(163.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681104997X/rz2668Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.85	1.82	2.601 (4)	151
C21—H21A⋯O1	0.93	2.54	3.300 (4)	139
C7—H7A⋯N2ⁱ	0.93	2.44	3.327 (9)	160

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by a start-up grant from Anyang Institute of Technology, China.

supplementary crystallographic information

Comment

Multi-component reactions (MCRs) (Hulme & Gore, 2003; Ugi, 1962) involving at least three starting materials in a one-pot reaction have attracted considerable attention in terms of saving both energy and raw materials (Devi & Bhuyan, 2004). Compared to conventional multi-step organic syntheses, MCRs have advantages that include the simplicity of a one-pot procedure and the buildup of complex molecules (Domling & Ugi, 2000). We report here the synthesis and crystal structure of the title compound, 4-4-[(2-hydroxynaphthalen-1-yl)(morpholino)methyl]benzonitrile.

In the title compound (Fig. 1) bond lengths and angles have normal values. The dihedral angle between the naphthalene ring system and the benzene ring is 81.25 (10)°. The morpholine ring (N1/C12/C13/O2/C14/C15) assumes a boat conformation, with puckering parameters <i<Q, θ and φ (Cremer & Pople, 1975) of 0.559 (4) Å, 179.3 (4)° and -159 (4)°, respectively. The molecular conformation is stabilized by intramolecular O—H···N and C—H···O hydrogen bonds (Table 1). In the crystal structure, molecules are linked into helical chains parallel to the c axis by intermolecular C—H···N hydrogen bonds.

Experimental

A dry 100 ml flask was charged with 4-formylbenzonitrile (15 mmol), naphthalen-2-ol (15 mmol) and morpholine (15 mmol). The mixture was stirred at 373 K for 12 h, then ethanol (15 ml) was added. After heating under reflux for 1 h, the precipitate was filtrated out and washed with ethanol (10 ml × 3) to give the title compound. Colourless crystals were obtained by slow evaporation of a dichloromethane solution.