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

Ling-Zhi Zhong; Kun Wang; Xiao-Yan Ma; Rui-Xiang Li

doi:10.1107/S1600536808020436

. 2008 Jul 9;64(Pt 8):o1438. doi: 10.1107/S1600536808020436

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

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

PMCID: PMC2962069 PMID: 21203153

Abstract

In the title compound, C₂₄H₂₁NO₂·C₂H₆O, the dihedral angle between the two aromatic ring systems is 87.00 (6)°. There is an intramolecular O—H⋯N hydrogen bond, which forms a six-membered ring. Intermolecular O—H⋯O 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,
a = 10.356 (5) Å
b = 10.702 (4) Å
c = 11.681 (6) Å
α = 94.74 (3)°
β = 113.53 (4)°
γ = 110.21 (3)°
V = 1076.7 (10) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.002
3 standard reflections every 300 reflections intensity decay: 2.1%

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.120
S = 0.94
3973 reflections
276 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020436/bt2737sup1.cif

e-64-o1438-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020436/bt2737Isup2.hkl

e-64-o1438-Isup2.hkl^{(194.7KB, hkl)}

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⋯O3ⁱ	0.82	1.92	2.738 (2)	175
O2—H2⋯N1	0.82	1.85	2.590 (3)	149
O3—H3⋯O2	0.82	2.19	2.939 (3)	151

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Binol and its derivatives have been largely used in asymmetric catalysis and chiral recognition (Pu, 1998). In this paper we present X-ray crystallographic analysis of the title compound .

As shown in Fig. 1, an intramolecular O—H···N hydrogen bond between the hydroxy and the imino moieties forms a ring.

In the crystal, the molecules are connected by O—H···O hydrogen bonds (Fig. 2).

Experimental

The salen ligand, 3-(n-propyliminomethyl)-1,1'-binaphthol was prepared by condensation of 3-carboxaldehyde-1,1'-binaphthol with n-propyamine, which was prepared by reported methods (Chin et al., 2004). Crystals suitable for X-ray analysis were obtained by slow evaporation of a ethanol /methylene chloride (1:5) solution of the compound.