1-[(4-Bromo­phen­yl)(morpholin-4-yl)meth­yl]naphthalen-2-ol

Zhao, Q.

doi:10.1107/S1600536812002620

Volume 68
Part 2
Page o529
February 2012

Received 11 January 2012
Accepted 20 January 2012
Online 31 January 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.045
wR = 0.102
Data-to-parameter ratio = 18.2
Details

1-[(4-Bromophenyl)(morpholin-4-yl)methyl]naphthalen-2-ol

Qun Zhao ^a ^*

^aSchool of Pharmaceutical Sciences, Nanjing University of Chinese Medicine, Nanjing 210046, People's Republic of China
Correspondence e-mail: qzhaonucm@gmail.com

The title compound, C₂₁H₂₀BrNO₂, was obtained from a condensation reaction of 4-bromobenzaldehyde, 2-naphthol and morpholine. The molecular conformation is stabilized by an intramolecular O-HN hydrogen bond, closing a six-membered ring. The dihedral angle between the naphthalene ring system and the benzene ring is 76.72 (8)°. In addition to the intramolecular hydrogen bond, the O-H groups of centrosymmetrically related molecules form short intermolecular HO contacts of 2.59 Å. These molecules are also linked by pairs of C-HO interactions, generating an R₂²(14) motif.

Related literature

For applications of Betti-type reactions, see: Lu et al. (2002); Xu et al. (2004); Wang et al. (2005).

Experimental

Crystal data

C₂₁H₂₀BrNO₂
M_r = 398.29
Monoclinic, P 2₁ /n
a = 11.024 (2) Å
b = 12.119 (2) Å
c = 13.875 (3) Å
= 104.55 (3)°
V = 1794.2 (6) Å³
Z = 4
Mo K radiation
= 2.31 mm^-1
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.802, T_max = 1.000
18164 measured reflections
4108 independent reflections
3021 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.102
S = 1.08
4108 reflections
226 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AN1	0.82	1.93	2.622 (3)	142
C13-H13AO1ⁱ	0.93	2.53	3.357 (4)	148
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: GK2449 ).

Acknowledgements

The authors are grateful to the starter fund of Nanjing University of Chinese Medicine.

References

Lu, J., Xu, X. N., Wang, C. D., He, J. G., Hu, Y. F. & Hu, H. W. (2002). Tetrahedron Lett. 43, 8367-8369.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, X. Y., Dong, Y. M., Sun, J. W., Xu, X. N., Li, R. & Hu, Y. F. (2005). J. Org. Chem. 70, 1897-1900.
Xu, X. N., Lu, J., Dong, Y. M., Li, R., Ge, Z. M. & Hu, Y. F. (2004). Tetrahedron Asymmetry, 15, 475-479.

organic compounds