5,5′-Seleno­bis­(2-hy­droxy­benzaldehyde)

Ming-Hu Wu; Wen-Ju Liu

doi:10.1107/S1600536811042097

. 2011 Oct 22;67(Pt 11):o2983. doi: 10.1107/S1600536811042097

5,5′-Selenobis(2-hydroxybenzaldehyde)

Ming-Hu Wu ^a,^*, Wen-Ju Liu ^b

PMCID: PMC3247385 PMID: 22220003

Abstract

In the title molecule, C₁₄H₁₀O₄Se, the dihedral angle between the two benzene rings is 74.6 (1)°. Both hydroxybenzaldehyde groups form intramolecular O—H⋯O hydrogen bonds. In the crystal, pairs of molecules are linked by pairs of weak C—H⋯π(arene) interactions, forming centrosymmetric dimers. In addition, molecules are linked by π–π stacking interactions, with a centroid–centroid distance of 3.785 (2) Å, forming chains along the c axis.

Related literature

For background to organo-selenium compounds, see: Mukherjee et al. (2006 ▶); Phadnis et al. (2005 ▶); Braga et al. (2005 ▶); Mugesh et al. (2001 ▶).

Experimental

Crystal data

C₁₄H₁₀O₄Se
M _r = 321.18
Monoclinic,
a = 7.7652 (5) Å
b = 11.9129 (8) Å
c = 13.3353 (9) Å
β = 90.304 (1)°
V = 1233.58 (14) Å³
Z = 4
Mo Kα radiation
μ = 3.05 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.461, T _max = 0.581
7045 measured reflections
2550 independent reflections
2041 reflections with I > 2σ(I)
R _int = 0.100

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.122
S = 1.08
2550 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042097/lh5352sup1.cif

e-67-o2983-sup1.cif^{(15.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042097/lh5352Isup2.hkl

e-67-o2983-Isup2.hkl^{(125.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042097/lh5352Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811042097/lh5352Isup4.cml

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

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

Cg is the centroid of the C8-C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.90	2.621 (4)	146
O3—H3A⋯O4	0.82	1.95	2.660 (4)	145
C10—H10⋯Cgⁱ	0.93	2.89	3.763 (3)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge financial support of this work as a project of Guangdong Provincial Department of Education.

supplementary crystallographic information

Comment

The organo-selenium nucleus is one of the most abundant structural nucleus found in natural products and biologically active molecules (e.g., seleno-carbohydrates,selenoamino acids,and seleno-peptides)(Mukherjee et al.,2006; Phadnis et al., 2005; Braga et al., 2005). Moreover, organoselenium compounds have emerged as an exceptional class of structures that exemplify a role in biochemical processes, serving as important therapeutic compounds ranging from antiviral and anticancer agents to a variety of situations where free radicals are involved (Mugesh et al., 2001). We are currently studing the synthesis of a new series of organoselenium compounds, such as selanes, diselenides and macrocyclic Schiff bases containing selenium atoms. Reported herein are the synthesis and X-ray structure of the title compound.

In the molecule (Fig. 1), the dihedral angle between the two benzene rings is 74.6 (1)°. Two intramolecular O—H···O hydrogen bonds are present in the molecule. The Se1—C1 and Se1—C8 bond lengths are the same within experimental error. The Se1—C1—C6—C5 and Se1—C8—C13—C12 torsional angles of -174.5 (2)° and -174.6 (2)°, respectively, indicate a slight deviation of the selenium atoms from the mean planes of the benzene rings.

In the crystal, pairs of molecules are linked by weak C—H···π (arene) interactions (see Table 1, Fig. 2). In addition, molecules are linked by Cg1···Cg2ⁱⁱ (symmetry code (ii): -1/2+x, 1/2-y, 1/2+z) and Cg2···Cg1 ⁱⁱⁱ (symmetry code (iii) : 1/2+x, 1/2-y, -1/2+z) π–π stacking interactions with a centroid-centroid distance of 3.785 (2)Å to form one-dimensional chains along the c axis (Fig. 3). Cg1 and Cg2 are the centroids of the C1-C6 and C8-C13 rings.

Experimental

A mixture of salicylaldehyde (87.93 g, 0.72 mol), selenium dioxide (26.63 g, 0.24 mol)and concentrated hydrochloric acid (132 ml) was stirred for 0.5 h at room temperature. Then, the mixture was further stirred for 50 h at 353 K. The resulting reddish brown solid was filtered, washed with water and ethanol. The obtained yellowish solid was recrystallized with ethyl acetate and etanol (v:v=5:1) to give yellowish crystals of the title compound in yield 20.8%, which are suitable for X-ray analysis.