5,5′-Seleno­bis­(2-hy­droxy­benzaldehyde)

Wu, M.-H.; Liu, W.-J.

doi:10.1107/S1600536811042097

organic compounds

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Volume 67| Part 11| November 2011| Page o2983

doi:10.1107/S1600536811042097

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5,5′-Selenobis(2-hydroxybenzaldehyde)

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

^aSchool of Chemistry and Chemical Engneering, Guangdong Pharmaceutical University, Guangzhou 510006, People's Republic of China, and ^bCollege of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: minghuwu@hotmail.com

(Received 8 October 2011; accepted 12 October 2011; online 22 October 2011)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.041
wR(F²) = 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

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
Symmetry code: (i) -x+2, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042097/lh5352sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811042097/lh5352Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536811042097/lh5352Isup4.cml

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing showing the hydrogen bonding interactions as thin solid lines. H atoms not involved in hydrogen bonds have been omitted.
	Fig. 3. Part of the crystal structure showing π–π stacking interactions between benzene rings as thin solid lines.

5,5'-Selenobis(2-hydroxybenzaldehyde) top

Crystal data top

C₁₄H₁₀O₄Se	F(000) = 640
M_r = 321.18	D_x = 1.729 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3183 reflections
a = 7.7652 (5) Å	θ = 2.3–27.8°
b = 11.9129 (8) Å	µ = 3.05 mm⁻¹
c = 13.3353 (9) Å	T = 296 K
β = 90.304 (1)°	Block, yellow
V = 1233.58 (14) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2550 independent reflections
Radiation source: fine-focus sealed tube	2041 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
ϕ and ω scans	θ_max = 26.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.461, T_max = 0.581	k = −10→14
7045 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0633P)²] where P = (F_o² + 2F_c²)/3
2550 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₁₄H₁₀O₄Se	V = 1233.58 (14) Å³
M_r = 321.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.7652 (5) Å	µ = 3.05 mm⁻¹
b = 11.9129 (8) Å	T = 296 K
c = 13.3353 (9) Å	0.30 × 0.20 × 0.20 mm
β = 90.304 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	2550 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2041 reflections with I > 2σ(I)
T_min = 0.461, T_max = 0.581	R_int = 0.100
7045 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.08	Δρ_max = 0.64 e Å⁻³
2550 reflections	Δρ_min = −0.54 e Å⁻³
172 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Se1	0.10731 (4)	0.81234 (3)	0.62308 (2)	0.04535 (18)
C8	0.0015 (4)	0.7027 (3)	0.7079 (2)	0.0347 (7)
C1	0.2434 (4)	0.7156 (3)	0.5393 (2)	0.0334 (6)
C5	0.5117 (4)	0.6774 (2)	0.4565 (2)	0.0340 (7)
C6	0.4134 (4)	0.7406 (3)	0.5238 (2)	0.0356 (7)
H6	0.4640	0.8000	0.5583	0.043*
O1	0.5229 (3)	0.5247 (2)	0.33974 (17)	0.0514 (6)
H1	0.6219	0.5483	0.3355	0.077*
C13	−0.1686 (4)	0.7131 (3)	0.7323 (2)	0.0369 (7)
H13	−0.2337	0.7699	0.7028	0.044*
C3	0.2627 (4)	0.5615 (3)	0.4229 (2)	0.0412 (7)
H3	0.2116	0.5011	0.3901	0.049*
O2	0.7856 (3)	0.6539 (2)	0.38446 (19)	0.0577 (7)
O4	−0.5065 (3)	0.5951 (2)	0.8838 (2)	0.0593 (7)
C4	0.4354 (4)	0.5874 (3)	0.4060 (2)	0.0350 (7)
C12	−0.2473 (4)	0.6400 (3)	0.8007 (2)	0.0366 (7)
C2	0.1688 (4)	0.6257 (3)	0.4884 (2)	0.0389 (7)
H2	0.0534	0.6089	0.4990	0.047*
C7	0.6922 (4)	0.7058 (3)	0.4396 (3)	0.0443 (8)
H7	0.7378	0.7674	0.4733	0.053*
C10	0.0214 (4)	0.5417 (3)	0.8167 (3)	0.0504 (9)
H10	0.0866	0.4834	0.8436	0.060*
C9	0.0956 (4)	0.6158 (3)	0.7512 (3)	0.0463 (8)
H9	0.2115	0.6077	0.7354	0.056*
C11	−0.1501 (4)	0.5530 (3)	0.8433 (3)	0.0456 (8)
O3	−0.2165 (3)	0.4793 (2)	0.9087 (2)	0.0676 (8)
H3A	−0.3182	0.4942	0.9183	0.101*
C14	−0.4287 (4)	0.6536 (3)	0.8254 (3)	0.0490 (8)
H14	−0.4889	0.7113	0.7941	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0460 (2)	0.0397 (2)	0.0505 (3)	0.00471 (13)	0.01921 (17)	−0.00162 (15)
C8	0.0277 (15)	0.0413 (18)	0.0351 (15)	0.0014 (12)	0.0057 (12)	−0.0033 (13)
C1	0.0240 (14)	0.0430 (16)	0.0332 (15)	0.0034 (12)	0.0040 (12)	−0.0008 (14)
C5	0.0275 (15)	0.0406 (17)	0.0339 (14)	−0.0006 (12)	0.0046 (12)	0.0039 (13)
C6	0.0374 (16)	0.0373 (17)	0.0320 (15)	−0.0022 (13)	0.0003 (13)	−0.0048 (14)
O1	0.0497 (13)	0.0560 (15)	0.0485 (13)	0.0027 (11)	0.0165 (11)	−0.0142 (12)
C13	0.0354 (16)	0.0412 (17)	0.0341 (15)	0.0065 (13)	0.0019 (13)	−0.0070 (14)
C3	0.0424 (17)	0.0436 (18)	0.0376 (16)	−0.0076 (14)	0.0034 (14)	−0.0079 (15)
O2	0.0352 (14)	0.0726 (17)	0.0653 (16)	0.0044 (12)	0.0168 (12)	−0.0026 (15)
O4	0.0416 (14)	0.0705 (18)	0.0661 (16)	−0.0140 (12)	0.0206 (12)	−0.0110 (14)
C4	0.0287 (14)	0.0457 (18)	0.0306 (14)	0.0029 (13)	0.0023 (12)	0.0015 (14)
C12	0.0291 (15)	0.0434 (18)	0.0373 (16)	−0.0036 (13)	0.0032 (13)	−0.0113 (14)
C2	0.0253 (15)	0.050 (2)	0.0410 (17)	−0.0050 (13)	0.0053 (13)	0.0005 (15)
C7	0.0268 (16)	0.058 (2)	0.0483 (18)	−0.0035 (14)	0.0002 (14)	0.0020 (17)
C10	0.0308 (16)	0.049 (2)	0.072 (2)	0.0094 (15)	0.0054 (16)	0.0137 (19)
C9	0.0317 (16)	0.050 (2)	0.058 (2)	0.0061 (14)	0.0081 (15)	−0.0037 (17)
C11	0.0453 (18)	0.0418 (19)	0.0496 (18)	−0.0030 (15)	0.0058 (15)	−0.0008 (17)
O3	0.0511 (15)	0.0664 (18)	0.086 (2)	−0.0042 (13)	0.0179 (14)	0.0289 (16)
C14	0.0383 (19)	0.058 (2)	0.0504 (19)	−0.0010 (16)	0.0074 (16)	−0.0098 (19)

Geometric parameters (Å, º) top

Se1—C8	1.916 (3)	C3—C4	1.395 (4)
Se1—C1	1.925 (3)	C3—H3	0.9300
C8—C13	1.368 (4)	O2—C7	1.206 (4)
C8—C9	1.391 (4)	O4—C14	1.209 (4)
C1—C6	1.370 (4)	C12—C11	1.401 (5)
C1—C2	1.392 (4)	C12—C14	1.457 (4)
C5—C4	1.396 (4)	C2—H2	0.9300
C5—C6	1.401 (4)	C7—H7	0.9300
C5—C7	1.461 (4)	C10—C9	1.370 (5)
C6—H6	0.9300	C10—C11	1.386 (5)
O1—C4	1.344 (4)	C10—H10	0.9300
O1—H1	0.8200	C9—H9	0.9300
C13—C12	1.403 (5)	C11—O3	1.343 (4)
C13—H13	0.9300	O3—H3A	0.8200
C3—C2	1.374 (4)	C14—H14	0.9300

C8—Se1—C1	99.96 (14)	C11—C12—C13	119.1 (3)
C13—C8—C9	118.3 (3)	C11—C12—C14	120.6 (3)
C13—C8—Se1	119.7 (2)	C13—C12—C14	120.2 (3)
C9—C8—Se1	121.8 (2)	C3—C2—C1	121.2 (3)
C6—C1—C2	119.5 (3)	C3—C2—H2	119.4
C6—C1—Se1	119.3 (2)	C1—C2—H2	119.4
C2—C1—Se1	121.0 (2)	O2—C7—C5	123.8 (3)
C4—C5—C6	119.4 (3)	O2—C7—H7	118.1
C4—C5—C7	120.6 (3)	C5—C7—H7	118.1
C6—C5—C7	120.0 (3)	C9—C10—C11	120.5 (3)
C1—C6—C5	120.5 (3)	C9—C10—H10	119.7
C1—C6—H6	119.7	C11—C10—H10	119.7
C5—C6—H6	119.7	C10—C9—C8	121.5 (3)
C4—O1—H1	109.5	C10—C9—H9	119.3
C8—C13—C12	121.5 (3)	C8—C9—H9	119.3
C8—C13—H13	119.2	O3—C11—C10	118.4 (3)
C12—C13—H13	119.2	O3—C11—C12	122.6 (3)
C2—C3—C4	119.5 (3)	C10—C11—C12	119.0 (3)
C2—C3—H3	120.2	C11—O3—H3A	109.5
C4—C3—H3	120.2	O4—C14—C12	124.7 (4)
O1—C4—C3	118.2 (3)	O4—C14—H14	117.7
O1—C4—C5	121.9 (3)	C12—C14—H14	117.7
C3—C4—C5	119.9 (3)

C1—Se1—C8—C13	−138.5 (3)	C8—C13—C12—C14	179.7 (3)
C1—Se1—C8—C9	45.8 (3)	C4—C3—C2—C1	−0.8 (5)
C8—Se1—C1—C6	−131.5 (3)	C6—C1—C2—C3	0.0 (5)
C8—Se1—C1—C2	53.3 (3)	Se1—C1—C2—C3	175.2 (2)
C2—C1—C6—C5	0.8 (5)	C4—C5—C7—O2	−1.6 (5)
Se1—C1—C6—C5	−174.5 (2)	C6—C5—C7—O2	178.4 (3)
C4—C5—C6—C1	−0.9 (5)	C11—C10—C9—C8	−1.3 (6)
C7—C5—C6—C1	179.2 (3)	C13—C8—C9—C10	0.1 (5)
C9—C8—C13—C12	1.3 (5)	Se1—C8—C9—C10	175.9 (3)
Se1—C8—C13—C12	−174.6 (2)	C9—C10—C11—O3	−179.1 (3)
C2—C3—C4—O1	−178.4 (3)	C9—C10—C11—C12	1.1 (6)
C2—C3—C4—C5	0.7 (5)	C13—C12—C11—O3	−179.5 (3)
C6—C5—C4—O1	179.2 (3)	C14—C12—C11—O3	−0.7 (5)
C7—C5—C4—O1	−0.8 (5)	C13—C12—C11—C10	0.2 (5)
C6—C5—C4—C3	0.1 (4)	C14—C12—C11—C10	179.0 (3)
C7—C5—C4—C3	−179.9 (3)	C11—C12—C14—O4	1.6 (5)
C8—C13—C12—C11	−1.4 (5)	C13—C12—C14—O4	−179.5 (3)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀O₄Se
M_r	321.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.7652 (5), 11.9129 (8), 13.3353 (9)
β (°)	90.304 (1)
V (Å³)	1233.58 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.05
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.461, 0.581
No. of measured, independent and observed [I > 2σ(I)] reflections	7045, 2550, 2041
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.122, 1.08
No. of reflections	2550
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.54

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)	145.8
O3—H3A···O4	0.82	1.95	2.660 (4)	145.1
C10—H10···Cgⁱ	0.93	2.89	3.763 (3)	158

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

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

References

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