(E)-3-Dimethyl-amino-1-(2,5-dimethyl-thio-phen-3-yl)prop-2-en-1-one.

In the title compound, C(11)H(15)NOS, the 3-(dimethyl-amino)-prop-2-en-1-one unit is approximately planar [maximum deviation = 0.0975 (14) Å] and its mean plane of seven non-H atoms makes a dihedral angle of 6.96 (10)° with the thio-phene ring. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds into inversion dimers with R(2) (2)(14) ring motifs. The dimers are stacked along the c axis through C-H⋯π inter-actions. The two methyl groups, attached to the thio-phene ring and the amino N atom, are each disordered over two orientations, with site-occupancy ratios of 0.59 (4):0.41 (4) and 0.74 (4):0.26 (4), respectively.

Related literature

For background to and the biological activity of thio­phene derivatives, see: Ghorab et al. (2006 ▶); Al-Said et al. (2011 ▶); Shaaban et al. (2010 ▶); Krantz et al. (1990 ▶); Kikugawa & Ichino (1973 ▶); Gogte et al. (1967 ▶); Medower et al. (2008 ▶); Ghorab et al. (1998 ▶); Hassan et al. (1998 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H15NOS

M = 209.30

Triclinic,

a = 5.9114 (2) Å

b = 7.5424 (2) Å

c = 13.9940 (4) Å

α = 81.274 (2)°

β = 88.828 (3)°

γ = 69.119 (3)°

V = 575.83 (3) Å3

Z = 2

Cu Kα radiation

μ = 2.24 mm−1

T = 296 K

0.82 × 0.15 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.260, T max = 0.859

7188 measured reflections

1897 independent reflections

1650 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.114

S = 1.08

1897 reflections

134 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021022/is5136sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021022/is5136Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021022/is5136Isup3.cml

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

C11H15NOS	Z = 2
Mr = 209.30	F(000) = 224
Triclinic, P1	Dx = 1.207 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 5.9114 (2) Å	Cell parameters from 967 reflections
b = 7.5424 (2) Å	θ = 3.2–67.4°
c = 13.9940 (4) Å	µ = 2.24 mm−1
α = 81.274 (2)°	T = 296 K
β = 88.828 (3)°	Plate, pink
γ = 69.119 (3)°	0.82 × 0.15 × 0.07 mm
V = 575.83 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	1897 independent reflections
Radiation source: fine-focus sealed tube	1650 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 65.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→5
Tmin = 0.260, Tmax = 0.859	k = −8→8
7188 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.1016P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1897 reflections	Δρmax = 0.16 e Å−3
134 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (2)

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	Occ. (<1)
S1	0.02985 (11)	0.64848 (8)	0.08507 (4)	0.0778 (3)
O1	0.0467 (3)	0.8400 (2)	0.37669 (10)	0.0842 (5)
N1	0.3675 (3)	1.2353 (2)	0.39674 (11)	0.0645 (4)
C1	−0.0007 (3)	0.7081 (3)	0.19944 (13)	0.0608 (5)
C2	0.1315 (3)	0.8191 (3)	0.21208 (12)	0.0572 (4)
C3	0.2590 (4)	0.8516 (3)	0.12684 (14)	0.0665 (5)
H3A	0.3579	0.9244	0.1232	0.080*
C4	0.2241 (4)	0.7685 (3)	0.05249 (15)	0.0722 (5)
C5	0.3269 (5)	0.7734 (4)	−0.04686 (17)	0.0935 (8)
H5A	0.4761	0.7964	−0.0444	0.140*	0.59 (4)
H5B	0.2134	0.8744	−0.0910	0.140*	0.59 (4)
H5C	0.3567	0.6526	−0.0686	0.140*	0.59 (4)
H5X	0.4875	0.6789	−0.0443	0.140*	0.41 (4)
H5Y	0.3329	0.8986	−0.0688	0.140*	0.41 (4)
H5Z	0.2258	0.7459	−0.0909	0.140*	0.41 (4)
C6	−0.1564 (4)	0.6318 (3)	0.26736 (16)	0.0741 (6)
H6A	−0.2750	0.7362	0.2930	0.111*
H6B	−0.0568	0.5417	0.3194	0.111*
H6C	−0.2368	0.5689	0.2330	0.111*
C7	0.1383 (3)	0.8968 (3)	0.30347 (13)	0.0591 (5)
C8	0.2539 (3)	1.0343 (3)	0.30342 (13)	0.0594 (5)
H8A	0.3279	1.0684	0.2480	0.071*
C9	0.2569 (3)	1.1156 (3)	0.38331 (13)	0.0580 (4)
H9A	0.1705	1.0833	0.4351	0.070*
C10	0.3421 (4)	1.3206 (3)	0.48415 (16)	0.0786 (6)
H10A	0.2444	1.2712	0.5282	0.118*
H10B	0.2658	1.4575	0.4684	0.118*
H10C	0.4992	1.2896	0.5139	0.118*
C11	0.5161 (5)	1.2903 (4)	0.3226 (2)	0.0893 (7)
H11A	0.6385	1.1771	0.3058	0.134*	0.74 (4)
H11B	0.5917	1.3690	0.3467	0.134*	0.74 (4)
H11C	0.4161	1.3613	0.2663	0.134*	0.74 (4)
H11X	0.6789	1.2527	0.3480	0.134*	0.26 (4)
H11Y	0.4512	1.4270	0.3030	0.134*	0.26 (4)
H11Z	0.5163	1.2276	0.2678	0.134*	0.26 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0865 (4)	0.0846 (4)	0.0703 (4)	−0.0331 (3)	0.0027 (3)	−0.0296 (3)
O1	0.1196 (13)	0.1037 (12)	0.0637 (8)	−0.0794 (10)	0.0170 (8)	−0.0201 (7)
N1	0.0697 (10)	0.0645 (9)	0.0719 (10)	−0.0393 (8)	0.0060 (7)	−0.0110 (7)
C1	0.0613 (10)	0.0593 (10)	0.0623 (10)	−0.0210 (8)	−0.0024 (8)	−0.0123 (8)
C2	0.0598 (10)	0.0558 (10)	0.0570 (10)	−0.0220 (8)	−0.0008 (7)	−0.0079 (8)
C3	0.0681 (12)	0.0701 (12)	0.0638 (11)	−0.0280 (10)	0.0062 (9)	−0.0105 (9)
C4	0.0711 (12)	0.0748 (13)	0.0616 (11)	−0.0145 (10)	0.0038 (9)	−0.0119 (9)
C5	0.1003 (18)	0.1024 (19)	0.0662 (13)	−0.0218 (14)	0.0163 (12)	−0.0163 (12)
C6	0.0784 (14)	0.0821 (14)	0.0782 (13)	−0.0463 (11)	0.0042 (10)	−0.0184 (10)
C7	0.0625 (11)	0.0611 (11)	0.0599 (10)	−0.0301 (9)	0.0011 (8)	−0.0078 (8)
C8	0.0635 (11)	0.0600 (11)	0.0603 (10)	−0.0294 (8)	0.0065 (8)	−0.0084 (8)
C9	0.0583 (10)	0.0559 (10)	0.0653 (10)	−0.0289 (8)	0.0025 (8)	−0.0050 (8)
C10	0.0951 (16)	0.0787 (14)	0.0786 (13)	−0.0489 (12)	−0.0018 (11)	−0.0164 (11)
C11	0.0905 (16)	0.0933 (16)	0.1066 (17)	−0.0600 (14)	0.0237 (13)	−0.0189 (13)

S1—C4	1.715 (2)	C5—H5Z	0.9600
S1—C1	1.7161 (19)	C6—H6A	0.9600
O1—C7	1.239 (2)	C6—H6B	0.9600
N1—C9	1.325 (2)	C6—H6C	0.9600
N1—C10	1.447 (3)	C7—C8	1.431 (3)
N1—C11	1.453 (3)	C8—C9	1.357 (3)
C1—C2	1.364 (3)	C8—H8A	0.9300
C1—C6	1.502 (3)	C9—H9A	0.9300
C2—C3	1.434 (3)	C10—H10A	0.9600
C2—C7	1.492 (3)	C10—H10B	0.9600
C3—C4	1.348 (3)	C10—H10C	0.9600
C3—H3A	0.9300	C11—H11A	0.9600
C4—C5	1.506 (3)	C11—H11B	0.9600
C5—H5A	0.9600	C11—H11C	0.9600
C5—H5B	0.9600	C11—H11X	0.9600
C5—H5C	0.9600	C11—H11Y	0.9600
C5—H5X	0.9600	C11—H11Z	0.9600
C5—H5Y	0.9600
C4—S1—C1	93.45 (9)	C1—C6—H6C	109.5
C9—N1—C10	121.97 (16)	H6A—C6—H6C	109.5
C9—N1—C11	121.03 (18)	H6B—C6—H6C	109.5
C10—N1—C11	116.98 (17)	O1—C7—C8	122.18 (17)
C2—C1—C6	131.23 (18)	O1—C7—C2	119.57 (17)
C2—C1—S1	110.76 (14)	C8—C7—C2	118.26 (16)
C6—C1—S1	118.00 (14)	C9—C8—C7	120.80 (17)
C1—C2—C3	111.44 (17)	C9—C8—H8A	119.6
C1—C2—C7	123.46 (16)	C7—C8—H8A	119.6
C3—C2—C7	125.09 (17)	N1—C9—C8	128.09 (17)
C4—C3—C2	114.75 (19)	N1—C9—H9A	116.0
C4—C3—H3A	122.6	C8—C9—H9A	116.0
C2—C3—H3A	122.6	N1—C10—H10A	109.5
C3—C4—C5	129.0 (2)	N1—C10—H10B	109.5
C3—C4—S1	109.58 (15)	H10A—C10—H10B	109.5
C5—C4—S1	121.38 (19)	N1—C10—H10C	109.5
C4—C5—H5A	109.5	H10A—C10—H10C	109.5
C4—C5—H5B	109.5	H10B—C10—H10C	109.5
C4—C5—H5C	109.5	N1—C11—H11A	109.5
C4—C5—H5X	109.5	N1—C11—H11B	109.5
C4—C5—H5Y	109.5	N1—C11—H11C	109.5
H5X—C5—H5Y	109.5	N1—C11—H11X	109.5
C4—C5—H5Z	109.5	N1—C11—H11Y	109.5
H5X—C5—H5Z	109.5	H11X—C11—H11Y	109.5
H5Y—C5—H5Z	109.5	N1—C11—H11Z	109.5
C1—C6—H6A	109.5	H11X—C11—H11Z	109.5
C1—C6—H6B	109.5	H11Y—C11—H11Z	109.5
H6A—C6—H6B	109.5
C4—S1—C1—C2	0.81 (15)	C1—S1—C4—C5	−179.91 (19)
C4—S1—C1—C6	−178.17 (16)	C1—C2—C7—O1	9.8 (3)
C6—C1—C2—C3	178.17 (19)	C3—C2—C7—O1	−170.80 (19)
S1—C1—C2—C3	−0.6 (2)	C1—C2—C7—C8	−170.86 (17)
C6—C1—C2—C7	−2.3 (3)	C3—C2—C7—C8	8.6 (3)
S1—C1—C2—C7	178.87 (14)	O1—C7—C8—C9	−3.3 (3)
C1—C2—C3—C4	0.1 (2)	C2—C7—C8—C9	177.32 (17)
C7—C2—C3—C4	−179.42 (18)	C10—N1—C9—C8	176.0 (2)
C2—C3—C4—C5	179.6 (2)	C11—N1—C9—C8	−2.5 (3)
C2—C3—C4—S1	0.5 (2)	C7—C8—C9—N1	175.62 (18)
C1—S1—C4—C3	−0.76 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.96	2.46	3.410 (3)	172
C5—H5B···Cg1ii	0.96	2.77	3.641 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/C1–C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1i	0.96	2.46	3.410 (3)	172
C5—H5B⋯Cg1ii	0.96	2.77	3.641 (3)	152

Symmetry codes: (i) ; (ii) .