3-(n-Propyl­imino­meth­yl)-1,1′-bi-2-naphthol ethanol solvate

Zhong, L.-Z.; Wang, K.; Ma, X.-Y.; Li, R.-X.

doi:10.1107/S1600536808020436

Volume 64
Part 8
Page o1438
August 2008

Received 28 June 2008
Accepted 3 July 2008
Online 9 July 2008

Key indicators
Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.004 Å
R = 0.046
wR = 0.120
Data-to-parameter ratio = 14.4
Details

3-(n-Propyliminomethyl)-1,1'-bi-2-naphthol ethanol solvate

Ling-Zhi Zhong,^a Kun Wang,^a Xiao-Yan Ma ^a and Rui-Xiang Li ^a ^*

^aInstitute of Homogeneous Catalysis, Department of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
Correspondence e-mail: sculiruixiang@163.com

In the title compound, C₂₄H₂₁NO₂·C₂H₆O, the dihedral angle between the two aromatic ring systems is 87.00 (6)°. There is an intramolecular O-HN hydrogen bond, which forms a six-membered ring. Intermolecular O-HO hydrogen bonds stabilize the crystal structure.

Related literature

For background on the application of salen complexes to asymmetric catalysis, see: Pu (1998). For synthesis, see: Chin et al. (2004).

Experimental

Crystal data

C₂₄H₂₁NO₂·C₂H₆O
M_r = 401.49
Triclinic, $[P \overline 1]$
a = 10.356 (5) Å
b = 10.702 (4) Å
c = 11.681 (6) Å
= 94.74 (3)°
= 113.53 (4)°
= 110.21 (3)°
V = 1076.7 (10) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 292 (2) K
0.42 × 0.40 × 0.38 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
3981 measured reflections
3973 independent reflections
1867 reflections with I > 2(I)
R_int = 0.002
3 standard reflections every 300 reflections intensity decay: 2.1%

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.120
S = 0.94
3973 reflections
276 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O3ⁱ	0.82	1.92	2.738 (2)	175
O2-H2N1	0.82	1.85	2.590 (3)	149
O3-H3O2	0.82	2.19	2.939 (3)	151
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); 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: BT2737 ).

References

Chin, J., Kim, D. C., Kim, H. J., Francis, B. P. & Kim, K. M. (2004). Org. Lett. 6, 2591-2593.
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association Pittsburgh Meeting. Abstract PA104.
Pu, L. (1998). Chem. Rev. 98, 2405-2494.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds