(2E)-2-(1,3-Benzo-thia-zol-2-yl)-3-(di-methyl-amino)-prop-2-ene-nitrile.

The mol-ecular conformation of title compound, C12H11N3S, is almost planar [maximum deviation = 0.063 (2) Å]; an intra-molecular C-H⋯N hydrogen bond is noted. In the crystal, mol-ecules inter-act with each other via π-π stacking inter-actions between thia-zole rings [centroid-centroid distance = 3.7475 (9) Å] and methyl-H⋯π(C6) inter-actions, forming columns along the a axis.

Related literature

For various biological activities (e.g. anti-tumour, anti-inflammatory, anti-viral, etc.) of benzo­thia­zole compounds, see: Selvam et al. (2011 ▶); Sanja & Cvetkovic (2011 ▶); Alang et al. (2010 ▶); Pal et al. (2011 ▶); Sharma et al. (2010 ▶); El-Shaaer et al. (1997 ▶); Gupta & Raat (2010 ▶); Hutchinson et al. (2002 ▶); Gong et al. (2004 ▶); Hutchinson et al. (2003 ▶); Geronikaki & Theophilidis (1992 ▶); Vicini et al. (1990 ▶); Das et al. (2003 ▶); Klose et al. (1983 ▶); Satsangi et al. (1983 ▶).

Experimental

Crystal data

C12H11N3S

M = 229.31

Monoclinic,

a = 7.3785 (2) Å

b = 20.1801 (4) Å

c = 8.2706 (2) Å

β = 112.947 (4)°

V = 1134.03 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.32 mm−1

T = 293 K

0.26 × 0.20 × 0.09 mm

Data collection

Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013 ▶) T min = 0.584, T max = 0.818

4062 measured reflections

2195 independent reflections

1971 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.05

2195 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2013 ▶); 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: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033266/tk5279sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033266/tk5279Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033266/tk5279Isup3.cml

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

C12H11N3S	F(000) = 480
Mr = 229.31	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 1971 reflections
a = 7.3785 (2) Å	θ = 4.4–72.7°
b = 20.1801 (4) Å	µ = 2.32 mm−1
c = 8.2706 (2) Å	T = 293 K
β = 112.947 (4)°	Block, purple
V = 1134.03 (6) Å3	0.26 × 0.20 × 0.09 mm
Z = 4

Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer	2195 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1971 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.016
ω scans	θmax = 72.7°, θmin = 4.4°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013)	h = −7→9
Tmin = 0.584, Tmax = 0.818	k = −16→25
4062 measured reflections	l = −10→8

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1211P] where P = (Fo2 + 2Fc2)/3
2195 reflections	(Δ/σ)max = 0.002
147 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S1	0.11365 (6)	0.50492 (2)	0.23607 (5)	0.0475 (1)
N1	0.24456 (18)	0.46002 (6)	0.55620 (16)	0.0427 (4)
N2	0.3152 (3)	0.66200 (8)	0.3024 (2)	0.0704 (6)
N3	0.5370 (2)	0.62896 (8)	0.81666 (18)	0.0544 (4)
C1	0.0527 (2)	0.42447 (7)	0.26748 (18)	0.0417 (4)
C2	0.1371 (2)	0.40931 (7)	0.44773 (19)	0.0403 (4)
C3	0.1078 (2)	0.34624 (8)	0.5022 (2)	0.0491 (5)
C4	−0.0040 (3)	0.30080 (8)	0.3794 (2)	0.0518 (5)
C5	−0.0886 (2)	0.31692 (9)	0.2020 (2)	0.0516 (5)
C6	−0.0608 (2)	0.37875 (9)	0.1440 (2)	0.0501 (5)
C7	0.2450 (2)	0.51233 (7)	0.46445 (18)	0.0388 (4)
C8	0.3437 (2)	0.57454 (7)	0.53589 (19)	0.0411 (4)
C9	0.4385 (2)	0.57944 (8)	0.7160 (2)	0.0459 (5)
C10	0.5596 (3)	0.69358 (10)	0.7510 (3)	0.0643 (6)
C11	0.6221 (4)	0.62098 (14)	1.0073 (3)	0.0817 (8)
C12	0.3318 (2)	0.62455 (8)	0.4120 (2)	0.0491 (5)
H3	0.16340	0.33490	0.62050	0.0590*
H4	−0.02320	0.25870	0.41570	0.0620*
H5	−0.16480	0.28570	0.12150	0.0620*
H6	−0.11670	0.38950	0.02530	0.0600*
H9	0.43210	0.54140	0.77700	0.0550*
H10A	0.62640	0.68910	0.67250	0.0960*
H10B	0.63510	0.72160	0.84750	0.0960*
H10C	0.43220	0.71290	0.68920	0.0960*
H11A	0.60670	0.57590	1.03660	0.1230*
H11B	0.55600	0.64990	1.05890	0.1230*
H11C	0.75950	0.63200	1.05180	0.1230*

	U11	U22	U33	U12	U13	U23
S1	0.0628 (3)	0.0411 (2)	0.0349 (2)	−0.0012 (2)	0.0150 (2)	0.0049 (1)
N1	0.0501 (7)	0.0382 (6)	0.0408 (6)	0.0023 (5)	0.0188 (5)	0.0008 (5)
N2	0.0975 (13)	0.0468 (8)	0.0584 (9)	−0.0053 (8)	0.0213 (8)	0.0088 (7)
N3	0.0544 (7)	0.0575 (8)	0.0464 (7)	−0.0001 (6)	0.0144 (6)	−0.0116 (6)
C1	0.0489 (7)	0.0408 (7)	0.0378 (7)	0.0023 (6)	0.0194 (6)	0.0037 (6)
C2	0.0457 (7)	0.0413 (7)	0.0365 (7)	0.0036 (6)	0.0189 (6)	0.0014 (5)
C3	0.0618 (9)	0.0453 (8)	0.0428 (8)	0.0007 (7)	0.0231 (7)	0.0065 (6)
C4	0.0642 (9)	0.0417 (8)	0.0567 (9)	−0.0033 (7)	0.0315 (7)	0.0019 (7)
C5	0.0575 (9)	0.0502 (8)	0.0518 (9)	−0.0093 (7)	0.0263 (7)	−0.0104 (7)
C6	0.0576 (9)	0.0546 (9)	0.0377 (7)	−0.0041 (7)	0.0180 (6)	−0.0027 (6)
C7	0.0443 (7)	0.0394 (7)	0.0336 (7)	0.0066 (5)	0.0162 (6)	0.0018 (5)
C8	0.0457 (7)	0.0369 (7)	0.0412 (7)	0.0041 (6)	0.0175 (6)	−0.0008 (6)
C9	0.0486 (8)	0.0454 (8)	0.0432 (8)	0.0039 (6)	0.0173 (6)	−0.0026 (6)
C10	0.0652 (10)	0.0537 (10)	0.0699 (11)	−0.0082 (8)	0.0219 (9)	−0.0178 (9)
C11	0.0848 (15)	0.0984 (17)	0.0464 (10)	−0.0053 (13)	0.0087 (9)	−0.0160 (11)
C12	0.0570 (9)	0.0379 (7)	0.0485 (8)	0.0002 (6)	0.0165 (7)	−0.0029 (6)

S1—C1	1.7311 (15)	C7—C8	1.456 (2)
S1—C7	1.7612 (14)	C8—C9	1.380 (2)
N1—C2	1.3878 (19)	C8—C12	1.416 (2)
N1—C7	1.3008 (19)	C3—H3	0.9300
N2—C12	1.150 (2)	C4—H4	0.9300
N3—C9	1.322 (2)	C5—H5	0.9300
N3—C10	1.447 (3)	C6—H6	0.9300
N3—C11	1.461 (3)	C9—H9	0.9300
C1—C2	1.407 (2)	C10—H10A	0.9600
C1—C6	1.389 (2)	C10—H10B	0.9600
C2—C3	1.395 (2)	C10—H10C	0.9600
C3—C4	1.378 (2)	C11—H11A	0.9600
C4—C5	1.391 (2)	C11—H11B	0.9600
C5—C6	1.381 (3)	C11—H11C	0.9600
C1—S1—C7	89.15 (7)	C2—C3—H3	120.00
C2—N1—C7	110.61 (12)	C4—C3—H3	120.00
C9—N3—C10	124.08 (15)	C3—C4—H4	120.00
C9—N3—C11	119.72 (17)	C5—C4—H4	119.00
C10—N3—C11	116.13 (18)	C4—C5—H5	120.00
S1—C1—C2	109.23 (10)	C6—C5—H5	120.00
S1—C1—C6	129.06 (12)	C1—C6—H6	121.00
C2—C1—C6	121.71 (14)	C5—C6—H6	121.00
N1—C2—C1	115.46 (13)	N3—C9—H9	114.00
N1—C2—C3	125.84 (13)	C8—C9—H9	115.00
C1—C2—C3	118.70 (13)	N3—C10—H10A	109.00
C2—C3—C4	119.52 (14)	N3—C10—H10B	109.00
C3—C4—C5	121.02 (16)	N3—C10—H10C	109.00
C4—C5—C6	120.77 (15)	H10A—C10—H10B	109.00
C1—C6—C5	118.27 (14)	H10A—C10—H10C	109.00
S1—C7—N1	115.55 (11)	H10B—C10—H10C	110.00
S1—C7—C8	119.17 (10)	N3—C11—H11A	109.00
N1—C7—C8	125.28 (13)	N3—C11—H11B	109.00
C7—C8—C9	117.55 (13)	N3—C11—H11C	109.00
C7—C8—C12	116.15 (13)	H11A—C11—H11B	109.00
C9—C8—C12	126.30 (14)	H11A—C11—H11C	110.00
N3—C9—C8	131.03 (15)	H11B—C11—H11C	109.00
N2—C12—C8	175.21 (17)
C7—S1—C1—C2	−0.33 (12)	S1—C1—C2—N1	0.48 (18)
C7—S1—C1—C6	179.26 (16)	S1—C1—C2—C3	−179.33 (12)
C1—S1—C7—C8	−179.85 (13)	N1—C2—C3—C4	179.54 (17)
C1—S1—C7—N1	0.14 (13)	C1—C2—C3—C4	−0.7 (2)
C2—N1—C7—C8	−179.91 (15)	C2—C3—C4—C5	−0.2 (3)
C7—N1—C2—C3	179.41 (16)	C3—C4—C5—C6	0.8 (3)
C2—N1—C7—S1	0.10 (19)	C4—C5—C6—C1	−0.4 (3)
C7—N1—C2—C1	−0.4 (2)	S1—C7—C8—C12	−2.3 (2)
C11—N3—C9—C8	179.2 (2)	N1—C7—C8—C9	−2.6 (2)
C10—N3—C9—C8	2.5 (3)	S1—C7—C8—C9	177.44 (12)
C6—C1—C2—C3	1.1 (2)	N1—C7—C8—C12	177.71 (15)
C6—C1—C2—N1	−179.15 (15)	C12—C8—C9—N3	0.5 (3)
S1—C1—C6—C5	179.96 (13)	C7—C8—C9—N3	−179.24 (17)
C2—C1—C6—C5	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1	0.93	2.44	2.851 (2)	106
C10—H10A···Cg1i	0.96	2.77	3.549 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N1	0.93	2.44	2.851 (2)	106
C10—H10A⋯Cg1i	0.96	2.77	3.549 (2)	138

Symmetry code: (i) .