Crystal structure of C-2-benzo-thia-zole-N-methyl-nitrone.

The mol-ecule of the title compound {systematic name: N-[(benzo-thia-zol-2-yl)methyl-idene]methyl-amine N-oxide}, C9H8N2OS, is close to planar [maximum deviation from the mean plane = 0.081 (2) Å], its conformation being stabilized by a strong intra-molecular attractive S⋯O inter-action [2.6977 (16) Å]. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of weak C-H⋯O hydrogen bonds.

Related literature

For the 1,3-dipolar cyclo­addition reaction of nitro­nes, see: Tufariello (1984 ▸); Torssell (1988 ▸). For the properties of benzo­thia­zole derivatives, see: Bradshaw et al. (2002 ▸); Paramashivappa et al. (2003 ▸); Jimonet et al. (1999 ▸); Ul-Hasan et al. (2002 ▸); Şener et al. (2000 ▸); Mruthyunjayaswamy & Shanthaveerappa (2000 ▸); Arpaci et al. (2002 ▸). For work by our group on nitro­nes, see: Doroschuk et al. (2006 ▸); Raspertova et al. (2002 ▸); Petkova et al. (2001 ▸). For attractive S—O inter­actions, see: Mokhir et al. (1999 ▸). For N—O bond lengths in nitro­nes, see: Ruano et al. (2012 ▸). For van der Waals radii, see: Wells (1986 ▸). For the synthesis, see: Delpierre & Lamchen (1965 ▸).

Experimental

Crystal data

C9H8N2OS

M = 192.23

Triclinic,

a = 5.5253 (14) Å

b = 7.4528 (19) Å

c = 10.839 (4) Å

α = 83.51 (2)°

β = 85.79 (3)°

γ = 77.39 (3)°

V = 432.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 294 K

0.4 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur 3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▸) T min = 0.423, T max = 0.994

3491 measured reflections

1933 independent reflections

1477 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.087

S = 1.00

1933 reflections

130 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015013262/rz5162sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013262/rz5162Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015013262/rz5162Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015013262/rz5162fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015013262/rz5162fig2.tif

Partial crystal packing of the title compound approximately viewed along [0 1 0], showing the formation of a dimeric unit through a pair of C—H⋯O hydrogen bonds (dashed lines).

CCDC reference: 1411951

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H8N2OS	Z = 2
Mr = 192.23	F(000) = 200
Triclinic, P1	Dx = 1.477 Mg m−3
a = 5.5253 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4528 (19) Å	Cell parameters from 110 reflections
c = 10.839 (4) Å	θ = 18.2–8.2°
α = 83.51 (2)°	µ = 0.33 mm−1
β = 85.79 (3)°	T = 294 K
γ = 77.39 (3)°	Block, colourless
V = 432.2 (2) Å3	0.4 × 0.3 × 0.2 mm

Oxford Diffraction Xcalibur 3 diffractometer	1477 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm-1	Rint = 0.018
ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −7→7
Tmin = 0.423, Tmax = 0.994	k = −9→9
3491 measured reflections	l = −14→14
1933 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0521P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1933 reflections	Δρmax = 0.24 e Å−3
130 parameters	Δρmin = −0.19 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
O1	0.0619 (2)	0.21490 (18)	0.72954 (11)	0.0573 (3)
S1	0.22145 (7)	0.17869 (5)	0.49058 (4)	0.04032 (14)
N1	−0.1621 (2)	0.29247 (17)	0.70659 (12)	0.0406 (3)
N2	−0.1774 (2)	0.33921 (18)	0.37522 (12)	0.0415 (3)
C1	−0.3325 (3)	0.3346 (3)	0.81411 (16)	0.0536 (4)
H1A	−0.2936	0.4351	0.8513	0.091 (8)*
H1B	−0.3159	0.2277	0.8738	0.078 (7)*
H1C	−0.5000	0.3688	0.7878	0.100 (8)*
C2	−0.2414 (3)	0.3343 (2)	0.59501 (14)	0.0402 (3)
H2	−0.4066	0.3938	0.5861	0.048 (5)*
C3	−0.0891 (3)	0.2941 (2)	0.48533 (14)	0.0366 (3)
C4	0.2333 (3)	0.1897 (2)	0.33030 (14)	0.0368 (3)
C5	0.4328 (3)	0.1236 (2)	0.25071 (15)	0.0423 (4)
H5	0.5858	0.0644	0.2813	0.049 (5)*
C6	0.3978 (3)	0.1484 (2)	0.12546 (16)	0.0470 (4)
H6	0.531 (3)	0.098 (2)	0.0729 (18)	0.058 (5)*
C7	0.1702 (3)	0.2371 (2)	0.07882 (15)	0.0503 (4)
H7	0.1516	0.2513	−0.0065	0.055 (5)*
C8	−0.0273 (3)	0.3040 (2)	0.15698 (15)	0.0483 (4)
H8	−0.1790	0.3640	0.1253	0.065 (6)*
C9	0.0036 (3)	0.2802 (2)	0.28572 (14)	0.0385 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0454 (7)	0.0711 (8)	0.0454 (7)	0.0102 (6)	−0.0084 (5)	−0.0037 (6)
S1	0.0344 (2)	0.0451 (2)	0.0377 (2)	0.00088 (15)	−0.00453 (15)	−0.00450 (15)
N1	0.0385 (7)	0.0394 (7)	0.0402 (7)	−0.0011 (5)	−0.0012 (5)	−0.0029 (5)
N2	0.0322 (7)	0.0500 (7)	0.0399 (7)	−0.0034 (6)	−0.0031 (5)	−0.0038 (6)
C1	0.0562 (11)	0.0594 (11)	0.0411 (9)	−0.0060 (8)	0.0077 (8)	−0.0069 (8)
C2	0.0344 (8)	0.0425 (8)	0.0415 (8)	−0.0033 (6)	−0.0033 (6)	−0.0032 (7)
C3	0.0331 (7)	0.0355 (8)	0.0404 (8)	−0.0051 (6)	−0.0043 (6)	−0.0030 (6)
C4	0.0367 (8)	0.0362 (7)	0.0375 (8)	−0.0072 (6)	−0.0035 (6)	−0.0035 (6)
C5	0.0374 (8)	0.0431 (8)	0.0443 (8)	−0.0024 (6)	−0.0012 (7)	−0.0082 (7)
C6	0.0472 (9)	0.0492 (9)	0.0443 (9)	−0.0083 (7)	0.0086 (7)	−0.0133 (7)
C7	0.0555 (10)	0.0605 (10)	0.0359 (8)	−0.0128 (8)	−0.0020 (7)	−0.0081 (8)
C8	0.0420 (9)	0.0608 (10)	0.0402 (9)	−0.0055 (7)	−0.0086 (7)	−0.0030 (8)
C9	0.0369 (8)	0.0410 (8)	0.0376 (8)	−0.0076 (6)	−0.0024 (6)	−0.0049 (6)

O1—N1	1.2763 (17)	C2—C3	1.426 (2)
S1—C3	1.7456 (16)	C4—C5	1.386 (2)
S1—C4	1.7269 (17)	C4—C9	1.393 (2)
N1—C1	1.461 (2)	C5—H5	0.9300
N1—C2	1.298 (2)	C5—C6	1.371 (2)
N2—C3	1.303 (2)	C6—H6	0.934 (19)
N2—C9	1.377 (2)	C6—C7	1.389 (3)
C1—H1A	0.9600	C7—H7	0.9300
C1—H1B	0.9600	C7—C8	1.371 (2)
C1—H1C	0.9600	C8—H8	0.9300
C2—H2	0.9300	C8—C9	1.405 (2)
C4—S1—C3	88.33 (8)	C5—C4—C9	121.64 (14)
O1—N1—C1	116.50 (13)	C9—C4—S1	109.96 (12)
O1—N1—C2	123.49 (13)	C4—C5—H5	121.0
C2—N1—C1	120.01 (13)	C6—C5—C4	117.98 (15)
C3—N2—C9	109.93 (12)	C6—C5—H5	121.0
N1—C1—H1A	109.5	C5—C6—H6	117.3 (12)
N1—C1—H1B	109.5	C5—C6—C7	121.45 (15)
N1—C1—H1C	109.5	C7—C6—H6	121.2 (12)
H1A—C1—H1B	109.5	C6—C7—H7	119.6
H1A—C1—H1C	109.5	C8—C7—C6	120.85 (15)
H1B—C1—H1C	109.5	C8—C7—H7	119.6
N1—C2—H2	118.2	C7—C8—H8	120.6
N1—C2—C3	123.58 (14)	C7—C8—C9	118.84 (16)
C3—C2—H2	118.2	C9—C8—H8	120.6
N2—C3—S1	116.37 (11)	N2—C9—C4	115.40 (14)
N2—C3—C2	121.29 (13)	N2—C9—C8	125.36 (14)
C2—C3—S1	122.33 (11)	C4—C9—C8	119.24 (15)
C5—C4—S1	128.40 (12)
O1—N1—C2—C3	1.7 (2)	C4—S1—C3—C2	178.11 (13)
S1—C4—C5—C6	179.91 (13)	C4—C5—C6—C7	0.1 (3)
S1—C4—C9—N2	−0.08 (17)	C5—C4—C9—N2	−179.70 (14)
S1—C4—C9—C8	−179.91 (12)	C5—C4—C9—C8	0.5 (2)
N1—C2—C3—S1	1.4 (2)	C5—C6—C7—C8	0.4 (3)
N1—C2—C3—N2	−179.90 (14)	C6—C7—C8—C9	−0.4 (3)
C1—N1—C2—C3	−178.46 (14)	C7—C8—C9—N2	−179.78 (15)
C3—S1—C4—C5	179.96 (15)	C7—C8—C9—C4	0.0 (2)
C3—S1—C4—C9	0.38 (11)	C9—N2—C3—S1	0.71 (17)
C3—N2—C9—C4	−0.39 (19)	C9—N2—C3—C2	−178.07 (13)
C3—N2—C9—C8	179.43 (15)	C9—C4—C5—C6	−0.5 (2)
C4—S1—C3—N2	−0.65 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.93	2.53	3.331 (2)	145

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C5H5O1i	0.93	2.53	3.331(2)	145

Symmetry code: (i) .