(E)-3-Dimethyl-amino-1-(1,3-thia-zol-2-yl)prop-2-en-1-one.

In the title compound, C8H10N2OS, the 3-(dimethyl-amino)-prop-2-en-1-one unit is approximately planar [give r.m.s. deviation] and the mean plane through the seven non-H atoms makes a dihedral angle of 8.88 (3)° with the thia-zole ring. The carbonyl and ring C=N double bonds adjacent to the carbonyl group are trans [N-C-C-O = 172.31 (15) °], while the conformation of the carbonyl and propene double bonds is cis [O-C-C-C = 2.2 (2)°]. In the crystal, short C-H⋯N and C-H⋯O inter-actions together with C-H⋯π inter-actions generate a three-dimensional network.

Related literature

For the biological activity of enaminone derivatives, see: Zeng (2010 ▶).

Experimental

Crystal data

C8H10N2OS

M = 182.24

Monoclinic,

a = 5.6252 (2) Å

b = 22.5957 (8) Å

c = 7.5777 (3) Å

β = 109.498 (4)°

V = 907.93 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 135 K

0.35 × 0.30 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.974, T max = 1.000

3683 measured reflections

1846 independent reflections

1565 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.090

S = 1.06

1846 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: OLEX2.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048817/vm2183sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048817/vm2183Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048817/vm2183Isup3.cml

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

C8H10N2OS	F(000) = 384
Mr = 182.24	Dx = 1.333 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 5.6252 (2) Å	Cell parameters from 1788 reflections
b = 22.5957 (8) Å	θ = 3.0–28.8°
c = 7.5777 (3) Å	µ = 0.31 mm−1
β = 109.498 (4)°	T = 135 K
V = 907.93 (6) Å3	Block, yellow
Z = 4	0.35 × 0.30 × 0.30 mm

Oxford Diffraction Xcalibur Eos diffractometer	1846 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	1565 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.0°
ω scans	h = −4→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −13→28
Tmin = 0.974, Tmax = 1.000	l = −9→8
3683 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0388P)2 + 0.2132P] where P = (Fo2 + 2Fc2)/3
1846 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.19, empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.48299 (8)	0.15794 (2)	0.44117 (6)	0.02965 (16)
O1	0.5387 (2)	0.06419 (5)	0.19443 (16)	0.0293 (3)
N1	0.8366 (2)	0.20354 (6)	0.34119 (19)	0.0269 (3)
N2	0.9036 (2)	0.06400 (6)	−0.19641 (18)	0.0243 (3)
C1	0.6877 (3)	0.15752 (7)	0.3145 (2)	0.0214 (4)
C2	0.6091 (3)	0.22388 (9)	0.5379 (2)	0.0347 (4)
H2	0.5586	0.2455	0.6269	0.042*
C3	0.7920 (3)	0.24077 (8)	0.4690 (2)	0.0336 (4)
H3	0.8841	0.2765	0.5073	0.040*
C4	0.6732 (3)	0.10684 (7)	0.1844 (2)	0.0215 (4)
C5	0.8103 (3)	0.11210 (7)	0.0581 (2)	0.0226 (4)
H5	0.9141	0.1456	0.0619	0.027*
C6	0.7890 (3)	0.06752 (7)	−0.0696 (2)	0.0221 (4)
H6	0.6800	0.0357	−0.0667	0.026*
C8	0.8565 (3)	0.01509 (8)	−0.3283 (2)	0.0308 (4)
H8A	0.7469	−0.0140	−0.2980	0.046*
H8B	1.0169	−0.0037	−0.3203	0.046*
H8C	0.7740	0.0300	−0.4556	0.046*
C9	1.0815 (3)	0.10914 (9)	−0.2102 (2)	0.0342 (4)
H9A	1.0028	0.1482	−0.2203	0.051*
H9B	1.1291	0.1017	−0.3214	0.051*
H9C	1.2324	0.1078	−0.0982	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0328 (3)	0.0320 (3)	0.0283 (3)	0.00526 (19)	0.0159 (2)	−0.00177 (19)
O1	0.0389 (7)	0.0259 (7)	0.0287 (6)	−0.0064 (6)	0.0186 (5)	−0.0032 (5)
N1	0.0274 (7)	0.0248 (8)	0.0253 (7)	0.0021 (6)	0.0046 (6)	−0.0015 (6)
N2	0.0267 (7)	0.0290 (8)	0.0204 (7)	0.0021 (6)	0.0121 (6)	0.0029 (6)
C1	0.0214 (8)	0.0238 (9)	0.0178 (8)	0.0062 (7)	0.0050 (6)	0.0029 (7)
C2	0.0428 (10)	0.0309 (10)	0.0292 (9)	0.0115 (9)	0.0102 (8)	−0.0059 (8)
C3	0.0378 (10)	0.0255 (10)	0.0318 (9)	0.0040 (8)	0.0040 (8)	−0.0064 (8)
C4	0.0232 (8)	0.0223 (8)	0.0179 (8)	0.0028 (7)	0.0052 (6)	0.0026 (7)
C5	0.0238 (8)	0.0235 (9)	0.0209 (8)	−0.0005 (7)	0.0079 (7)	0.0018 (7)
C6	0.0225 (8)	0.0253 (9)	0.0190 (8)	0.0021 (7)	0.0077 (6)	0.0055 (7)
C8	0.0439 (10)	0.0298 (10)	0.0247 (9)	0.0073 (8)	0.0193 (8)	0.0019 (8)
C9	0.0297 (9)	0.0466 (12)	0.0299 (9)	−0.0064 (9)	0.0148 (8)	0.0032 (9)

S1—C1	1.7282 (16)	C3—H3	0.9500
S1—C2	1.707 (2)	C4—C5	1.420 (2)
O1—C4	1.2432 (19)	C5—H5	0.9500
N1—C1	1.308 (2)	C5—C6	1.374 (2)
N1—C3	1.368 (2)	C6—H6	0.9500
N2—C6	1.3264 (19)	C8—H8A	0.9800
N2—C8	1.454 (2)	C8—H8B	0.9800
N2—C9	1.457 (2)	C8—H8C	0.9800
C1—C4	1.495 (2)	C9—H9A	0.9800
C2—H2	0.9500	C9—H9B	0.9800
C2—C3	1.355 (3)	C9—H9C	0.9800
C2—S1—C1	89.13 (9)	C6—C5—C4	118.28 (15)
C1—N1—C3	109.85 (14)	C6—C5—H5	120.9
C6—N2—C8	121.51 (14)	N2—C6—C5	127.23 (16)
C6—N2—C9	121.45 (15)	N2—C6—H6	116.4
C8—N2—C9	117.04 (13)	C5—C6—H6	116.4
N1—C1—S1	114.87 (12)	N2—C8—H8A	109.5
N1—C1—C4	127.05 (14)	N2—C8—H8B	109.5
C4—C1—S1	118.07 (12)	N2—C8—H8C	109.5
S1—C2—H2	125.0	H8A—C8—H8B	109.5
C3—C2—S1	109.92 (14)	H8A—C8—H8C	109.5
C3—C2—H2	125.0	H8B—C8—H8C	109.5
N1—C3—H3	121.9	N2—C9—H9A	109.5
C2—C3—N1	116.23 (17)	N2—C9—H9B	109.5
C2—C3—H3	121.9	N2—C9—H9C	109.5
O1—C4—C1	116.99 (14)	H9A—C9—H9B	109.5
O1—C4—C5	125.77 (15)	H9A—C9—H9C	109.5
C5—C4—C1	117.22 (14)	H9B—C9—H9C	109.5
C4—C5—H5	120.9
S1—C1—C4—O1	−9.54 (19)	C1—C4—C5—C6	−176.53 (13)
S1—C1—C4—C5	169.33 (11)	C2—S1—C1—N1	−0.70 (13)
S1—C2—C3—N1	0.2 (2)	C2—S1—C1—C4	−179.08 (13)
O1—C4—C5—C6	2.2 (2)	C3—N1—C1—S1	0.92 (17)
N1—C1—C4—O1	172.31 (15)	C3—N1—C1—C4	179.13 (15)
N1—C1—C4—C5	−8.8 (2)	C4—C5—C6—N2	−179.08 (15)
C1—S1—C2—C3	0.25 (14)	C8—N2—C6—C5	−177.66 (15)
C1—N1—C3—C2	−0.7 (2)	C9—N2—C6—C5	2.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1i	0.95	2.62	3.560 (2)	169
C6—H6···O1ii	0.95	2.60	3.462 (2)	151
C8—H8A···O1ii	0.98	2.31	3.269 (2)	167
C9—H9C···O1iii	0.98	2.51	3.433 (2)	157
C9—H9A···Cg1iv	0.98	2.93	3.549 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/N1/C1–C3 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1i	0.95	2.62	3.560 (2)	169
C6—H6⋯O1ii	0.95	2.60	3.462 (2)	151
C8—H8A⋯O1ii	0.98	2.31	3.269 (2)	167
C9—H9C⋯O1iii	0.98	2.51	3.433 (2)	157
C9—H9A⋯Cg1iv	0.98	2.93	3.549 (2)	122

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .