2-(3H-1,3-Benzothia-zol-2-yl-idene)-propane-dial.

In the title compound, C(10)H(7)NO(2)S, the dihedral angle between the benzimidazole and malonaldehyde group is 1.41 (2)°. An intra-molecular hydrogen bond is formed between the NH group and one of the adjacent carbonyl O atoms. In addition, the NH group forms an inter-molecular hydrogen bond to a symmetry equivalent of this carbonyl O atom, connecting the mol-ecules into centrosymmetric dimers. The structure also contains C-H⋯O inter-molecular inter-actions.

Related literature

For biological activities of benzothia­zole derivatives, see: Mortimer et al. (2006 ▶); Yoshida et al. (2005 ▶); Vicini et al. (2003 ▶).

Experimental

Crystal data

C10H7NO2S

M = 205.23

Monoclinic,

a = 8.3927 (10) Å

b = 5.0972 (8) Å

c = 20.739 (2) Å

β = 100.098 (8)°

V = 873.4 (2) Å3

Z = 4

Cu Kα radiation

μ = 3.05 mm−1

T = 133 K

0.12 × 0.12 × 0.02 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.711, T max = 0.942

10660 measured reflections

1569 independent reflections

1475 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.165

S = 1.02

1569 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (van der Sluis & Spek, 1990 ▶; Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811030248/hg5064sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030248/hg5064Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030248/hg5064Isup3.cml

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

C10H7NO2S	F(000) = 424
Mr = 205.23	Dx = 1.561 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 1475 reflections
a = 8.3927 (10) Å	θ = 7.5–71.9°
b = 5.0972 (8) Å	µ = 3.05 mm−1
c = 20.739 (2) Å	T = 133 K
β = 100.098 (8)°	Plate, colourless
V = 873.4 (2) Å3	0.12 × 0.12 × 0.02 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	1569 independent reflections
Radiation source: micro-focus rotating anode	1475 reflections with I > 2σ(I)
confocal	Rint = 0.082
ω scans	θmax = 71.9°, θmin = 7.5°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −10→10
Tmin = 0.711, Tmax = 0.942	k = −4→5
10660 measured reflections	l = −25→25

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.098P)2 + 1.503P] where P = (Fo2 + 2Fc2)/3
1569 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.45 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	0.6870 (3)	0.3667 (6)	0.16032 (14)	0.0291 (7)
H1	0.6162	0.2210	0.1600	0.035*
C2	0.7501 (3)	0.4952 (7)	0.21783 (13)	0.0311 (7)
H2	0.7216	0.4366	0.2578	0.037*
C3	0.8986 (3)	0.7993 (6)	0.16137 (14)	0.0272 (6)
H3	0.9706	0.9434	0.1619	0.033*
C4	0.8343 (3)	0.6732 (6)	0.10311 (13)	0.0256 (6)
C5	0.7315 (3)	0.4596 (6)	0.10291 (13)	0.0255 (6)
N6	0.6804 (3)	0.3641 (5)	0.03972 (11)	0.0248 (6)
H6	0.6145	0.2294	0.0313	0.030*
C7	0.7391 (3)	0.4926 (6)	−0.00706 (13)	0.0248 (6)
S8	0.86490 (8)	0.74932 (13)	0.02434 (3)	0.0253 (3)
C9	0.7044 (3)	0.4279 (6)	−0.07455 (13)	0.0267 (7)
C10	0.6013 (3)	0.2122 (6)	−0.09676 (14)	0.0267 (7)
H10	0.5856	0.1748	−0.1423	0.032*
O11	0.5306 (2)	0.0694 (4)	−0.06329 (9)	0.0303 (5)
C12	0.8543 (4)	0.7080 (6)	0.21876 (14)	0.0308 (7)
H12	0.8955	0.7919	0.2592	0.037*
C13	0.7714 (3)	0.5777 (6)	−0.12103 (14)	0.0303 (7)
H13	0.7447	0.5248	−0.1655	0.036*
O14	0.8605 (3)	0.7691 (4)	−0.10910 (11)	0.0343 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0248 (13)	0.0302 (18)	0.0337 (14)	0.0004 (12)	0.0085 (11)	0.0039 (12)
C2	0.0296 (14)	0.037 (2)	0.0280 (14)	0.0031 (13)	0.0094 (11)	0.0059 (12)
C3	0.0231 (13)	0.0296 (17)	0.0300 (14)	0.0009 (12)	0.0079 (11)	−0.0012 (12)
C4	0.0205 (12)	0.0312 (17)	0.0266 (13)	0.0034 (11)	0.0087 (10)	0.0026 (12)
C5	0.0197 (12)	0.0278 (17)	0.0294 (14)	0.0042 (11)	0.0052 (10)	−0.0001 (11)
N6	0.0200 (11)	0.0268 (15)	0.0287 (11)	−0.0004 (10)	0.0071 (8)	−0.0004 (9)
C7	0.0176 (12)	0.0264 (17)	0.0318 (14)	0.0032 (11)	0.0084 (10)	0.0007 (11)
S8	0.0225 (4)	0.0277 (5)	0.0274 (5)	−0.0021 (2)	0.0090 (3)	0.0003 (2)
C9	0.0213 (13)	0.0307 (18)	0.0295 (14)	0.0040 (11)	0.0082 (10)	0.0010 (11)
C10	0.0218 (13)	0.0316 (18)	0.0277 (14)	0.0040 (11)	0.0070 (11)	0.0002 (11)
O11	0.0262 (10)	0.0315 (13)	0.0341 (10)	−0.0017 (8)	0.0083 (8)	0.0019 (9)
C12	0.0295 (15)	0.0367 (19)	0.0263 (14)	0.0045 (12)	0.0053 (11)	−0.0022 (12)
C13	0.0276 (14)	0.0352 (19)	0.0303 (14)	0.0030 (13)	0.0109 (11)	0.0003 (12)
O14	0.0333 (12)	0.0377 (15)	0.0353 (12)	−0.0053 (9)	0.0151 (9)	0.0016 (9)

C1—C2	1.382 (4)	N6—C7	1.334 (4)
C1—C5	1.392 (4)	N6—H6	0.8800
C1—H1	0.9500	C7—C9	1.418 (4)
C2—C12	1.391 (4)	C7—S8	1.735 (3)
C2—H2	0.9500	C9—C13	1.421 (4)
C3—C12	1.388 (4)	C9—C10	1.425 (4)
C3—C4	1.391 (4)	C10—O11	1.228 (4)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.388 (4)	C12—H12	0.9500
C4—S8	1.741 (3)	C13—O14	1.228 (4)
C5—N6	1.393 (3)	C13—H13	0.9500
C2—C1—C5	117.2 (3)	C5—N6—H6	122.6
C2—C1—H1	121.4	N6—C7—C9	124.4 (3)
C5—C1—H1	121.4	N6—C7—S8	112.0 (2)
C1—C2—C12	121.8 (3)	C9—C7—S8	123.5 (2)
C1—C2—H2	119.1	C7—S8—C4	90.23 (13)
C12—C2—H2	119.1	C7—C9—C13	120.5 (3)
C12—C3—C4	117.9 (3)	C7—C9—C10	120.4 (3)
C12—C3—H3	121.0	C13—C9—C10	119.1 (3)
C4—C3—H3	121.0	O11—C10—C9	126.9 (3)
C5—C4—C3	120.7 (3)	O11—C10—H10	116.5
C5—C4—S8	111.4 (2)	C9—C10—H10	116.5
C3—C4—S8	127.8 (2)	C3—C12—C2	120.8 (3)
C4—C5—C1	121.6 (3)	C3—C12—H12	119.6
C4—C5—N6	111.4 (2)	C2—C12—H12	119.6
C1—C5—N6	126.9 (3)	O14—C13—C9	126.2 (3)
C7—N6—C5	114.9 (2)	O14—C13—H13	116.9
C7—N6—H6	122.6	C9—C13—H13	116.9
C5—C1—C2—C12	−0.2 (4)	C9—C7—S8—C4	−179.5 (2)
C12—C3—C4—C5	−1.2 (4)	C5—C4—S8—C7	0.0 (2)
C12—C3—C4—S8	178.5 (2)	C3—C4—S8—C7	−179.7 (3)
C3—C4—C5—C1	1.1 (4)	N6—C7—C9—C13	179.4 (2)
S8—C4—C5—C1	−178.7 (2)	S8—C7—C9—C13	−1.0 (4)
C3—C4—C5—N6	179.7 (3)	N6—C7—C9—C10	−0.3 (4)
S8—C4—C5—N6	−0.1 (3)	S8—C7—C9—C10	179.3 (2)
C2—C1—C5—C4	−0.3 (4)	C7—C9—C10—O11	2.1 (4)
C2—C1—C5—N6	−178.7 (3)	C13—C9—C10—O11	−177.7 (3)
C4—C5—N6—C7	0.2 (3)	C4—C3—C12—C2	0.7 (4)
C1—C5—N6—C7	178.7 (3)	C1—C2—C12—C3	0.0 (5)
C5—N6—C7—C9	179.4 (2)	C7—C9—C13—O14	−0.4 (5)
C5—N6—C7—S8	−0.2 (3)	C10—C9—C13—O14	179.3 (3)
N6—C7—S8—C4	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O11	0.88	2.13	2.731 (3)	125.
N6—H6···O11i	0.88	2.13	2.926 (3)	151.
C3—H3···O14ii	0.95	2.43	3.297 (4)	152.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O11	0.88	2.13	2.731 (3)	125
N6—H6⋯O11i	0.88	2.13	2.926 (3)	151
C3—H3⋯O14ii	0.95	2.43	3.297 (4)	152

Symmetry codes: (i) ; (ii) .