5,5'-Seleno-bis-(2-hy-droxy-benzaldehyde).

In the title mol-ecule, C(14)H(10)O(4)Se, the dihedral angle between the two benzene rings is 74.6 (1)°. Both hy-droxy-benzaldehyde groups form intra-molecular O-H⋯O hydrogen bonds. In the crystal, pairs of mol-ecules are linked by pairs of weak C-H⋯π(arene) inter-actions, forming centrosymmetric dimers. In addition, mol-ecules are linked by π-π stacking inter-actions, 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 = 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

Δρmax = 0.64 e Å−3

Δρmin = −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.

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

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

C14H10O4Se	F(000) = 640
Mr = 321.18	Dx = 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

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

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(Fo2) + (0.0633P)2] where P = (Fo2 + 2Fc2)/3
2550 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .