1,3-Benzothia-zole-2(3H)-selone.

The title compound, C(7)H(5)NSSe, is the product of the reaction of 2-chloro-benzothia-zole with sodium hydro-selenide. The mol-ecule is almost planar (r.m.s. deviation = 0.018 Å) owing to the presence of the long chain of conjugated bonds (Se=C-N-C=C-C=C-C=C). The geometrical parameters correspond well to those of the analog N-methyl-benzothia-zole-2(3H)-selone, demonstrating that the S atom does not take a significant role in the electron delocalization within the mol-ecule. In the crystal, mol-ecules form centrosymmetric dimers by means of inter-molecular N-H⋯Se hydrogen bonds. The dimers have a nonplanar ladder-like structure. Furthermore, the dimers are linked into ribbons propagating in [010] by weak attractive Se⋯S [3.7593 (4) Å] inter-actions.

Related literature

For selones as potential anti­thyroid drugs, see: Taurog et al. (1994 ▶); Roy & Mugesh (2005 ▶, 2006 ▶); Roy et al. (2007 ▶, 2011 ▶). For 2,3-dihydro-1,3-benzothia­zolo-2-selone synthesis, see: Warner (1963 ▶); Shibata & Mitsunobu (1992 ▶). For related compounds, see: Guziec & Guziec (1994 ▶); Husebye et al. (1997 ▶); Landry et al. (2006 ▶); Nakanishi et al. (2008 ▶).

Experimental

Crystal data

C7H5NSSe

M = 214.15

Monoclinic,

a = 8.0420 (4) Å

b = 6.0818 (3) Å

c = 15.1836 (7) Å

β = 101.195 (1)°

V = 728.50 (6) Å3

Z = 4

Mo Kα radiation

μ = 5.35 mm−1

T = 100 K

0.30 × 0.21 × 0.18 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.297, T max = 0.446

8129 measured reflections

2108 independent reflections

2042 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.016

wR(F 2) = 0.041

S = 1.00

2108 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043339/rk2309sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043339/rk2309Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043339/rk2309Isup3.cml

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

C7H5NSSe	F(000) = 416
Mr = 214.15	Dx = 1.952 Mg m−3
Monoclinic, P21/n	Melting point = 346–347 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.0420 (4) Å	Cell parameters from 6338 reflections
b = 6.0818 (3) Å	θ = 2.6–30.0°
c = 15.1836 (7) Å	µ = 5.35 mm−1
β = 101.195 (1)°	T = 100 K
V = 728.50 (6) Å3	Prism, pale-yellow
Z = 4	0.30 × 0.21 × 0.18 mm

Bruker SMART 1K CCD diffractometer	2108 independent reflections
Radiation source: fine-focus sealed tube	2042 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
Tmin = 0.297, Tmax = 0.446	k = −8→8
8129 measured reflections	l = −20→21

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)] = 0.016	Hydrogen site location: difference Fourier map
wR(F2) = 0.041	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.023P)2 + 0.371P] where P = (Fo2 + 2Fc2)/3
2108 reflections	(Δ/σ)max = 0.001
91 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > σF2 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
Se1	1.277060 (14)	0.076249 (19)	0.579287 (8)	0.01478 (5)
S1	1.17970 (3)	0.51668 (5)	0.661496 (19)	0.01522 (6)
C2	1.12217 (14)	0.27701 (18)	0.60187 (7)	0.01301 (19)
N3	0.95281 (12)	0.26504 (16)	0.57732 (6)	0.01391 (18)
H3	0.9022	0.1543	0.5457	0.017*
C3A	0.86204 (14)	0.43853 (18)	0.60496 (8)	0.0126 (2)
C4	0.68634 (15)	0.4594 (2)	0.59126 (8)	0.0155 (2)
H4	0.6135	0.3500	0.5601	0.019*
C5	0.62189 (15)	0.6465 (2)	0.62499 (8)	0.0170 (2)
H5	0.5026	0.6659	0.6160	0.020*
C6	0.72815 (15)	0.8072 (2)	0.67190 (8)	0.0167 (2)
H6	0.6801	0.9335	0.6940	0.020*
C7	0.90347 (15)	0.7839 (2)	0.68649 (8)	0.0160 (2)
H7	0.9762	0.8923	0.7185	0.019*
C7A	0.96916 (14)	0.59737 (19)	0.65275 (8)	0.0133 (2)

	U11	U22	U33	U12	U13	U23
Se1	0.01251 (7)	0.01418 (7)	0.01708 (7)	0.00142 (4)	0.00145 (4)	−0.00172 (4)
S1	0.01046 (12)	0.01552 (13)	0.01887 (13)	−0.00113 (9)	0.00088 (10)	−0.00449 (10)
C2	0.0133 (5)	0.0130 (5)	0.0125 (5)	0.0000 (4)	0.0020 (4)	0.0006 (4)
N3	0.0125 (4)	0.0132 (4)	0.0155 (4)	−0.0010 (3)	0.0015 (3)	−0.0021 (3)
C3A	0.0121 (5)	0.0134 (5)	0.0123 (5)	−0.0008 (4)	0.0022 (4)	0.0001 (4)
C4	0.0124 (5)	0.0177 (5)	0.0158 (5)	−0.0016 (4)	0.0013 (4)	0.0001 (4)
C5	0.0128 (5)	0.0219 (6)	0.0168 (5)	0.0018 (4)	0.0040 (4)	0.0019 (4)
C6	0.0172 (5)	0.0179 (5)	0.0159 (5)	0.0032 (4)	0.0052 (4)	0.0001 (4)
C7	0.0160 (5)	0.0163 (5)	0.0154 (5)	0.0000 (4)	0.0024 (4)	−0.0026 (4)
C7A	0.0114 (5)	0.0149 (5)	0.0134 (5)	−0.0012 (4)	0.0021 (4)	−0.0009 (4)

Se1—C2	1.8236 (11)	C4—C5	1.3890 (17)
S1—C2	1.7308 (12)	C4—H4	0.9500
S1—C7A	1.7430 (12)	C5—C6	1.3986 (17)
C2—N3	1.3425 (14)	C5—H5	0.9500
N3—C3A	1.3933 (14)	C6—C7	1.3913 (16)
N3—H3	0.8800	C6—H6	0.9500
C3A—C4	1.3935 (16)	C7—C7A	1.3906 (16)
C3A—C7A	1.3997 (15)	C7—H7	0.9500
C2—S1—C7A	92.31 (5)	C4—C5—C6	121.69 (11)
N3—C2—S1	110.16 (8)	C4—C5—H5	119.2
N3—C2—Se1	127.21 (9)	C6—C5—H5	119.2
S1—C2—Se1	122.63 (6)	C7—C6—C5	120.67 (11)
C2—N3—C3A	115.97 (10)	C7—C6—H6	119.7
C2—N3—H3	122.0	C5—C6—H6	119.7
C3A—N3—H3	122.0	C7A—C7—C6	118.04 (11)
N3—C3A—C4	126.82 (10)	C7A—C7—H7	121.0
N3—C3A—C7A	111.91 (10)	C6—C7—H7	121.0
C4—C3A—C7A	121.25 (10)	C7—C7A—C3A	120.96 (11)
C5—C4—C3A	117.37 (11)	C7—C7A—S1	129.39 (9)
C5—C4—H4	121.3	C3A—C7A—S1	109.64 (8)
C3A—C4—H4	121.3
C7A—S1—C2—N3	0.42 (9)	C5—C6—C7—C7A	0.29 (18)
C7A—S1—C2—Se1	−179.05 (7)	C6—C7—C7A—C3A	0.46 (17)
S1—C2—N3—C3A	−1.00 (13)	C6—C7—C7A—S1	−178.39 (9)
Se1—C2—N3—C3A	178.44 (8)	N3—C3A—C7A—C7	−179.85 (10)
C2—N3—C3A—C4	−177.14 (11)	C4—C3A—C7A—C7	−1.41 (17)
C2—N3—C3A—C7A	1.19 (14)	N3—C3A—C7A—S1	−0.80 (12)
N3—C3A—C4—C5	179.72 (11)	C4—C3A—C7A—S1	177.64 (9)
C7A—C3A—C4—C5	1.53 (17)	C2—S1—C7A—C7	179.17 (12)
C3A—C4—C5—C6	−0.77 (18)	C2—S1—C7A—C3A	0.22 (9)
C4—C5—C6—C7	−0.13 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Se1i	0.88	2.56	3.4165 (10)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Se1i	0.88	2.56	3.4165 (10)	163

Symmetry code: (i) .