4-(5-Chloro-thio-phen-2-yl)-1,2,3-selenadiazole.

In the title compound, C6H3ClN2SSe, the selenadiazole and chloro-thio-phene rings are almost coplanar [dihedral angle = 5.24 (15)°]. In the crystal, C-H⋯N inter-actions link the mol-ecules into chains extending along the b-axis direction. C-H⋯π inter-actions also occur.

Related literature

For the biological activity of selenadiazole derivatives, see: El-Bahaie et al. (1990 ▶); El-Kashef et al. (1986 ▶); Padmavathi et al. (2002 ▶); Plano et al. (2010 ▶); Stadtman (1991 ▶); Velusamy et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H3ClN2SSe

M = 249.57

Monoclinic,

a = 6.0412 (3) Å

b = 19.5870 (11) Å

c = 7.2010 (4) Å

β = 110.257 (3)°

V = 799.38 (7) Å3

Z = 4

Mo Kα radiation

μ = 5.22 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.330, T max = 0.391

7064 measured reflections

1978 independent reflections

1558 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.121

S = 1.01

1978 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049549/bt6854sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049549/bt6854Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049549/bt6854Isup3.cml

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

C6H3ClN2SSe	F(000) = 480
Mr = 249.57	Dx = 2.074 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1558 reflections
a = 6.0412 (3) Å	θ = 2.1–28.3°
b = 19.5870 (11) Å	µ = 5.22 mm−1
c = 7.2010 (4) Å	T = 293 K
β = 110.257 (3)°	Black, white crystalline
V = 799.38 (7) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	1978 independent reflections
Radiation source: fine-focus sealed tube	1558 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→6
Tmin = 0.330, Tmax = 0.391	k = −25→26
7064 measured reflections	l = −9→9

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0716P)2 + 0.3075P] where P = (Fo2 + 2Fc2)/3
1978 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.52 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
C1	0.3771 (6)	0.60797 (19)	0.2132 (5)	0.0397 (7)
H1	0.5288	0.6078	0.2081	0.048*
C2	0.2578 (6)	0.55180 (18)	0.2343 (4)	0.0333 (7)
C3	0.3344 (6)	0.48114 (17)	0.2494 (5)	0.0328 (7)
C4	0.5358 (6)	0.45391 (19)	0.2353 (5)	0.0412 (8)
H4	0.6532	0.4799	0.2134	0.049*
C5	0.5478 (6)	0.38256 (19)	0.2573 (5)	0.0413 (8)
H5	0.6726	0.3562	0.2502	0.050*
C6	0.3579 (6)	0.35688 (18)	0.2896 (5)	0.0376 (7)
Cl1	0.29911 (17)	0.27326 (5)	0.32523 (15)	0.0529 (3)
N1	−0.0347 (5)	0.62617 (17)	0.2239 (5)	0.0482 (8)
N2	0.0334 (5)	0.56419 (16)	0.2406 (4)	0.0428 (7)
S1	0.15880 (15)	0.41890 (5)	0.29606 (14)	0.0408 (2)
Se1	0.19762 (7)	0.684213 (19)	0.19625 (6)	0.04757 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0304 (16)	0.0409 (19)	0.0469 (18)	0.0004 (14)	0.0120 (14)	−0.0018 (15)
C2	0.0271 (15)	0.0379 (18)	0.0349 (15)	−0.0008 (12)	0.0107 (12)	−0.0014 (13)
C3	0.0286 (15)	0.0333 (16)	0.0368 (15)	−0.0044 (13)	0.0120 (13)	−0.0002 (13)
C4	0.0325 (17)	0.0404 (19)	0.056 (2)	−0.0015 (14)	0.0216 (15)	0.0038 (16)
C5	0.0336 (17)	0.042 (2)	0.055 (2)	0.0011 (14)	0.0232 (16)	−0.0024 (16)
C6	0.0353 (17)	0.0351 (18)	0.0427 (17)	−0.0030 (14)	0.0138 (14)	−0.0027 (14)
Cl1	0.0501 (6)	0.0375 (5)	0.0727 (6)	−0.0066 (4)	0.0234 (5)	0.0031 (4)
N1	0.0335 (15)	0.0461 (19)	0.068 (2)	0.0029 (13)	0.0221 (15)	0.0005 (15)
N2	0.0308 (14)	0.0443 (18)	0.0577 (18)	−0.0008 (13)	0.0208 (13)	−0.0007 (14)
S1	0.0289 (4)	0.0409 (5)	0.0559 (5)	−0.0041 (3)	0.0190 (4)	0.0004 (4)
Se1	0.0375 (2)	0.0371 (3)	0.0659 (3)	0.00047 (14)	0.01514 (19)	0.00089 (16)

C1—C2	1.352 (5)	C4—H4	0.9300
C1—Se1	1.825 (4)	C5—C6	1.345 (5)
C1—H1	0.9300	C5—H5	0.9300
C2—N2	1.394 (4)	C6—Cl1	1.714 (4)
C2—C3	1.451 (5)	C6—S1	1.721 (4)
C3—C4	1.364 (5)	N1—N2	1.274 (4)
C3—S1	1.724 (3)	N1—Se1	1.870 (3)
C4—C5	1.406 (5)
C2—C1—Se1	110.2 (3)	C5—C4—H4	123.4
C2—C1—H1	124.9	C6—C5—C4	112.2 (3)
Se1—C1—H1	124.9	C6—C5—H5	123.9
C1—C2—N2	115.1 (3)	C4—C5—H5	123.9
C1—C2—C3	128.0 (3)	C5—C6—Cl1	128.1 (3)
N2—C2—C3	116.9 (3)	C5—C6—S1	112.7 (3)
C4—C3—C2	129.5 (3)	Cl1—C6—S1	119.2 (2)
C4—C3—S1	111.3 (3)	N2—N1—Se1	111.1 (2)
C2—C3—S1	119.2 (2)	N1—N2—C2	116.7 (3)
C3—C4—C5	113.1 (3)	C3—S1—C6	90.63 (17)
C3—C4—H4	123.4	C1—Se1—N1	86.89 (15)
Se1—C1—C2—N2	−0.7 (4)	C4—C5—C6—S1	−0.4 (4)
Se1—C1—C2—C3	178.8 (3)	Se1—N1—N2—C2	−0.3 (4)
C1—C2—C3—C4	−4.0 (6)	C1—C2—N2—N1	0.7 (5)
N2—C2—C3—C4	175.4 (3)	C3—C2—N2—N1	−178.8 (3)
C1—C2—C3—S1	174.7 (3)	C4—C3—S1—C6	−1.4 (3)
N2—C2—C3—S1	−5.8 (4)	C2—C3—S1—C6	179.7 (3)
C2—C3—C4—C5	−179.7 (3)	C5—C6—S1—C3	1.0 (3)
S1—C3—C4—C5	1.4 (4)	Cl1—C6—S1—C3	−179.5 (2)
C3—C4—C5—C6	−0.7 (5)	C2—C1—Se1—N1	0.4 (3)
C4—C5—C6—Cl1	−179.8 (3)	N2—N1—Se1—C1	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1i	0.93	2.62	3.545 (5)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N1i	0.93	2.62	3.545 (5)	171

Symmetry code: (i) .