2-(Phenyl-selenon-yl)pyridine.

In the title compound, C11H9NO2Se, the pyridine and phenyl rings are almost perpendicular, with the dihedral angle between their mean planes being 79.16 (7)°. In the crystal, the mol-ecules pack so as to form ruffled sheets in the (110) plane connected by weak C-H⋯O inter-actions. In addition, there are weak π-π inter-actions between the mean planes of both the phenyl [centroid-centroid perpendicular distance of 3.591 (2) Å and slippage of 1.854 (2) Å] and pyridine rings [centroid-centroid perpendicular distance of 3.348 (2) Å and slippage of 1.854 (2) Å].

Related literature

For the pharmacological activity of selenone derivatives, see: Abdel-Hafez & Hussein (2008 ▶); Zhao et al. (2012 ▶); Hassan et al. (2011 ▶); Bhabak et al. (2011 ▶). For the chemistry of selenium compounds bonded directly to pyridine, see: Bhasin et al. (2013 ▶). For the synthesis of pharmaceuticals, see: Nogueira & Rocha (2011 ▶). For the synthesis of perfumes, fine chemicals and polymers, see: Zeng et al. (2013 ▶).

Experimental

Crystal data

C11H9NO2Se

M = 266.15

Triclinic,

a = 6.1598 (5) Å

b = 7.7223 (6) Å

c = 11.4952 (7) Å

α = 80.683 (6)°

β = 83.494 (6)°

γ = 74.614 (7)°

V = 518.83 (7) Å3

Z = 2

Mo Kα radiation

μ = 3.60 mm−1

T = 123 K

0.50 × 0.26 × 0.16 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: analytical (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.383, T max = 0.613

8688 measured reflections

5196 independent reflections

3965 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.090

S = 1.01

5196 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.76 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813029978/jj2170sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029978/jj2170Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029978/jj2170Isup3.cml

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

C11H9NO2Se	Z = 2
Mr = 266.15	F(000) = 264
Triclinic, P1	Dx = 1.704 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1598 (5) Å	Cell parameters from 2941 reflections
b = 7.7223 (6) Å	θ = 3.1–37.5°
c = 11.4952 (7) Å	µ = 3.60 mm−1
α = 80.683 (6)°	T = 123 K
β = 83.494 (6)°	Triangular plate, colorless
γ = 74.614 (7)°	0.50 × 0.26 × 0.16 mm
V = 518.83 (7) Å3

Agilent Xcalibur (Ruby, Gemini) diffractometer	5196 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3965 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 10.5081 pixels mm-1	θmax = 37.6°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: analytical (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −12→13
Tmin = 0.383, Tmax = 0.613	l = −18→19
8688 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0241P)2] where P = (Fo2 + 2Fc2)/3
5196 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.76 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Se	0.80434 (4)	0.23043 (3)	0.224458 (18)	0.02645 (6)
O1	1.0283 (3)	0.2030 (2)	0.13351 (14)	0.0370 (4)
O2	0.6629 (3)	0.0770 (2)	0.24217 (15)	0.0380 (4)
N1A	0.6710 (4)	0.6075 (3)	0.17338 (18)	0.0397 (5)
C1A	0.5932 (3)	0.4583 (3)	0.17700 (17)	0.0247 (4)
C2A	0.3857 (3)	0.4556 (3)	0.14449 (17)	0.0277 (4)
H2AA	0.3426	0.3453	0.1487	0.033*
C3A	0.2427 (4)	0.6216 (4)	0.10521 (19)	0.0358 (5)
H3AA	0.0978	0.6274	0.0816	0.043*
C4A	0.3131 (5)	0.7786 (3)	0.1008 (2)	0.0427 (6)
H4AA	0.2166	0.8929	0.0741	0.051*
C5A	0.5245 (5)	0.7685 (3)	0.1354 (2)	0.0453 (7)
H5AA	0.5696	0.8777	0.1327	0.054*
C1B	0.8984 (4)	0.2491 (3)	0.37495 (17)	0.0256 (4)
C2B	0.7332 (4)	0.3166 (3)	0.45649 (18)	0.0298 (4)
H2BA	0.5799	0.3593	0.4382	0.036*
C3B	0.7969 (4)	0.3207 (4)	0.5661 (2)	0.0399 (6)
H3BA	0.6853	0.3666	0.6251	0.048*
C4B	1.0186 (4)	0.2598 (3)	0.5925 (2)	0.0369 (5)
H4BA	1.0587	0.2646	0.6691	0.044*
C5B	1.1842 (4)	0.1913 (3)	0.50800 (19)	0.0339 (5)
H5BA	1.3373	0.1479	0.5267	0.041*
C6B	1.1244 (4)	0.1864 (3)	0.39527 (18)	0.0290 (4)
H6BA	1.2344	0.1419	0.3351	0.035*

	U11	U22	U33	U12	U13	U23
Se	0.02928 (11)	0.02457 (10)	0.02608 (11)	−0.00452 (8)	−0.00550 (7)	−0.00652 (8)
O1	0.0355 (9)	0.0416 (10)	0.0296 (8)	0.0001 (7)	0.0011 (6)	−0.0110 (7)
O2	0.0452 (10)	0.0285 (8)	0.0461 (10)	−0.0152 (7)	−0.0171 (8)	−0.0027 (7)
N1A	0.0512 (13)	0.0364 (11)	0.0364 (11)	−0.0169 (10)	−0.0067 (9)	−0.0069 (9)
C1A	0.0273 (9)	0.0254 (9)	0.0207 (8)	−0.0040 (7)	−0.0021 (7)	−0.0053 (7)
C2A	0.0274 (10)	0.0341 (11)	0.0219 (9)	−0.0085 (8)	0.0002 (7)	−0.0044 (8)
C3A	0.0293 (11)	0.0469 (14)	0.0254 (10)	−0.0010 (10)	0.0005 (8)	−0.0044 (10)
C4A	0.0578 (16)	0.0332 (12)	0.0253 (11)	0.0083 (11)	0.0003 (10)	−0.0052 (10)
C5A	0.078 (2)	0.0304 (12)	0.0326 (12)	−0.0202 (13)	−0.0063 (12)	−0.0063 (10)
C1B	0.0283 (10)	0.0251 (9)	0.0233 (9)	−0.0062 (8)	−0.0023 (7)	−0.0033 (8)
C2B	0.0265 (10)	0.0337 (11)	0.0262 (10)	−0.0013 (8)	−0.0007 (7)	−0.0070 (9)
C3B	0.0440 (14)	0.0417 (14)	0.0281 (11)	0.0002 (11)	0.0024 (9)	−0.0092 (10)
C4B	0.0481 (14)	0.0371 (12)	0.0248 (10)	−0.0079 (11)	−0.0055 (9)	−0.0051 (9)
C5B	0.0323 (11)	0.0383 (12)	0.0318 (11)	−0.0101 (10)	−0.0096 (9)	0.0003 (10)
C6B	0.0255 (10)	0.0334 (11)	0.0271 (10)	−0.0071 (8)	−0.0004 (7)	−0.0032 (9)

Se—O1	1.6218 (16)	C5A—H5AA	0.9500
Se—O2	1.6234 (16)	C1B—C2B	1.359 (3)
Se—C1B	1.9240 (19)	C1B—C6B	1.381 (3)
Se—C1A	1.929 (2)	C2B—C3B	1.368 (3)
N1A—C1A	1.354 (3)	C2B—H2BA	0.9500
N1A—C5A	1.367 (3)	C3B—C4B	1.373 (3)
C1A—C2A	1.378 (3)	C3B—H3BA	0.9500
C2A—C3A	1.388 (3)	C4B—C5B	1.385 (3)
C2A—H2AA	0.9500	C4B—H4BA	0.9500
C3A—C4A	1.383 (4)	C5B—C6B	1.395 (3)
C3A—H3AA	0.9500	C5B—H5BA	0.9500
C4A—C5A	1.383 (4)	C6B—H6BA	0.9500
C4A—H4AA	0.9500
O1—Se—O2	117.59 (9)	N1A—C5A—H5AA	118.8
O1—Se—C1B	106.80 (8)	C4A—C5A—H5AA	118.8
O2—Se—C1B	109.14 (8)	C2B—C1B—C6B	124.39 (19)
O1—Se—C1A	110.40 (9)	C2B—C1B—Se	116.78 (16)
O2—Se—C1A	106.21 (9)	C6B—C1B—Se	118.75 (15)
C1B—Se—C1A	106.17 (8)	C1B—C2B—C3B	117.2 (2)
C1A—N1A—C5A	115.3 (2)	C1B—C2B—H2BA	121.4
N1A—C1A—C2A	126.1 (2)	C3B—C2B—H2BA	121.4
N1A—C1A—Se	115.30 (16)	C2B—C3B—C4B	121.4 (2)
C2A—C1A—Se	118.53 (16)	C2B—C3B—H3BA	119.3
C1A—C2A—C3A	116.9 (2)	C4B—C3B—H3BA	119.3
C1A—C2A—H2AA	121.6	C3B—C4B—C5B	120.3 (2)
C3A—C2A—H2AA	121.6	C3B—C4B—H4BA	119.8
C4A—C3A—C2A	119.4 (2)	C5B—C4B—H4BA	119.8
C4A—C3A—H3AA	120.3	C4B—C5B—C6B	119.5 (2)
C2A—C3A—H3AA	120.3	C4B—C5B—H5BA	120.3
C3A—C4A—C5A	119.8 (2)	C6B—C5B—H5BA	120.3
C3A—C4A—H4AA	120.1	C1B—C6B—C5B	117.1 (2)
C5A—C4A—H4AA	120.1	C1B—C6B—H6BA	121.4
N1A—C5A—C4A	122.5 (2)	C5B—C6B—H6BA	121.4
C5A—N1A—C1A—C2A	1.2 (3)	O1—Se—C1B—C2B	164.23 (17)
C5A—N1A—C1A—Se	177.60 (16)	O2—Se—C1B—C2B	−67.68 (19)
O1—Se—C1A—N1A	−60.19 (17)	C1A—Se—C1B—C2B	46.41 (19)
O2—Se—C1A—N1A	171.30 (15)	O1—Se—C1B—C6B	−18.7 (2)
C1B—Se—C1A—N1A	55.21 (17)	O2—Se—C1B—C6B	109.38 (18)
O1—Se—C1A—C2A	116.53 (16)	C1A—Se—C1B—C6B	−136.53 (18)
O2—Se—C1A—C2A	−11.98 (18)	C6B—C1B—C2B—C3B	−0.6 (4)
C1B—Se—C1A—C2A	−128.08 (16)	Se—C1B—C2B—C3B	176.31 (18)
N1A—C1A—C2A—C3A	−0.5 (3)	C1B—C2B—C3B—C4B	0.3 (4)
Se—C1A—C2A—C3A	−176.84 (14)	C2B—C3B—C4B—C5B	−0.3 (4)
C1A—C2A—C3A—C4A	−0.1 (3)	C3B—C4B—C5B—C6B	0.7 (4)
C2A—C3A—C4A—C5A	0.0 (3)	C2B—C1B—C6B—C5B	0.9 (3)
C1A—N1A—C5A—C4A	−1.2 (3)	Se—C1B—C6B—C5B	−175.90 (16)
C3A—C4A—C5A—N1A	0.7 (4)	C4B—C5B—C6B—C1B	−0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2AA···O1i	0.95	2.50	3.331 (3)	146
C4A—H4AA···O1ii	0.95	2.53	3.341 (3)	143
C5A—H5AA···O2iii	0.95	2.35	3.188 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2A—H2AA⋯O1i	0.95	2.50	3.331 (3)	146
C4A—H4AA⋯O1ii	0.95	2.53	3.341 (3)	143
C5A—H5AA⋯O2iii	0.95	2.35	3.188 (3)	146

Symmetry codes: (i) ; (ii) ; (iii) .