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

In the title compound, C(15)H(13)NO(3)S, the benzene ring and the five-membered heterocyclic ring are oriented at a dihedral angle of 12.00 (6)°. In the crystal, C-H⋯O inter-actions generate two types of cyclic motifs, R(2) (2)(14) and R(2) (2)(26), connecting the mol-ecules into tapes extending along [101]. In addition, there are π-π stacking inter-actions between the benzene and thio-phene rings with centroid-centroid distances of 3.7263 (14) and 3.7487 (14) Å.

Related literature

For the synthesis of similar compounds, see: Asiri & Khan (2010 ▶, 2011 ▶); Kalirajan et al. (2009 ▶); Patil et al. (2009 ▶); Sarojini et al. (2006 ▶). For related structures and background references, see: Asiri et al. (2010a ▶,b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H13NO3S

M = 287.32

Monoclinic,

a = 7.3802 (5) Å

b = 13.7973 (9) Å

c = 13.4638 (8) Å

β = 96.997 (3)°

V = 1360.77 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.25 × 0.22 × 0.20 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.945, T max = 0.955

10732 measured reflections

2466 independent reflections

1493 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.117

S = 1.03

2466 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) text, I. DOI: 10.1107/S1600536811047933/gk2432sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047933/gk2432Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047933/gk2432Isup3.cml

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

C15H13NO3S	F(000) = 600
Mr = 287.32	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1493 reflections
a = 7.3802 (5) Å	θ = 2.1–25.3°
b = 13.7973 (9) Å	µ = 0.24 mm−1
c = 13.4638 (8) Å	T = 296 K
β = 96.997 (3)°	Prism, yellow
V = 1360.77 (15) Å3	0.25 × 0.22 × 0.20 mm
Z = 4

Bruker KAPPA APEXII CCD diffractometer	2466 independent reflections
Radiation source: fine-focus sealed tube	1493 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.1°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→16
Tmin = 0.945, Tmax = 0.955	l = −16→16
10732 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.0228P] where P = (Fo2 + 2Fc2)/3
2466 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.25 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 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	0.21173 (10)	0.46796 (5)	0.18440 (5)	0.0520 (3)
O1	0.4422 (3)	−0.10573 (18)	0.51656 (15)	0.0876 (10)
O2	0.5017 (3)	−0.25617 (17)	0.49723 (15)	0.0892 (10)
O3	0.0404 (3)	0.17111 (14)	0.06130 (14)	0.0744 (8)
N1	0.4392 (3)	−0.1786 (2)	0.46575 (18)	0.0607 (10)
C1	0.2331 (3)	−0.07879 (19)	0.22025 (18)	0.0413 (9)
C2	0.3105 (3)	−0.08450 (19)	0.32014 (17)	0.0431 (9)
C3	0.3587 (3)	−0.17332 (19)	0.36030 (18)	0.0444 (9)
C4	0.3343 (4)	−0.2574 (2)	0.3066 (2)	0.0577 (11)
C5	0.2586 (4)	−0.2528 (2)	0.2088 (2)	0.0618 (11)
C6	0.2074 (4)	−0.1642 (2)	0.1663 (2)	0.0530 (10)
C7	0.1775 (3)	0.01281 (19)	0.17143 (19)	0.0457 (10)
C8	0.2028 (4)	0.10257 (19)	0.20395 (18)	0.0490 (10)
C9	0.1319 (4)	0.1860 (2)	0.14180 (18)	0.0491 (10)
C10	0.1748 (3)	0.28475 (18)	0.17826 (18)	0.0419 (9)
C11	0.1514 (3)	0.36459 (18)	0.11758 (18)	0.0438 (9)
C12	0.0882 (4)	0.3718 (2)	0.00750 (18)	0.0616 (11)
C13	0.2414 (3)	0.31061 (19)	0.27906 (17)	0.0439 (9)
C14	0.2659 (3)	0.40587 (19)	0.29503 (17)	0.0433 (9)
C15	0.3299 (4)	0.4582 (2)	0.39024 (19)	0.0597 (11)
H2	0.32910	−0.02870	0.35879	0.0517*
H4	0.36845	−0.31670	0.33608	0.0691*
H5	0.24165	−0.30911	0.17094	0.0742*
H6	0.15459	−0.16188	0.10004	0.0636*
H7	0.11464	0.00698	0.10753	0.0548*
H8	0.26607	0.11362	0.26696	0.0588*
H12A	−0.04283	0.37068	−0.00322	0.0925*
H12B	0.13538	0.31800	−0.02658	0.0925*
H12C	0.13152	0.43128	−0.01806	0.0925*
H13	0.26568	0.26483	0.32962	0.0527*
H15A	0.45201	0.48132	0.38808	0.0894*
H15B	0.32800	0.41479	0.44581	0.0894*
H15C	0.25052	0.51215	0.39790	0.0894*

	U11	U22	U33	U12	U13	U23
S1	0.0670 (5)	0.0373 (4)	0.0511 (4)	0.0052 (4)	0.0043 (3)	0.0067 (3)
O1	0.132 (2)	0.0787 (18)	0.0482 (13)	0.0074 (15)	−0.0048 (13)	−0.0029 (13)
O2	0.120 (2)	0.0730 (16)	0.0699 (16)	0.0207 (15)	−0.0078 (14)	0.0294 (13)
O3	0.1077 (17)	0.0512 (13)	0.0544 (12)	−0.0006 (12)	−0.0302 (12)	0.0031 (10)
N1	0.0710 (17)	0.0627 (19)	0.0483 (16)	0.0049 (15)	0.0073 (12)	0.0161 (15)
C1	0.0439 (16)	0.0344 (15)	0.0453 (15)	−0.0035 (13)	0.0037 (12)	0.0001 (13)
C2	0.0515 (17)	0.0361 (16)	0.0420 (15)	0.0013 (13)	0.0067 (12)	−0.0021 (13)
C3	0.0471 (17)	0.0411 (17)	0.0445 (15)	−0.0004 (14)	0.0036 (12)	0.0072 (14)
C4	0.067 (2)	0.0354 (17)	0.069 (2)	0.0034 (15)	0.0018 (16)	0.0096 (16)
C5	0.079 (2)	0.0352 (17)	0.068 (2)	−0.0013 (16)	−0.0044 (17)	−0.0073 (15)
C6	0.0605 (19)	0.0453 (18)	0.0500 (16)	−0.0025 (15)	−0.0066 (14)	−0.0031 (15)
C7	0.0500 (17)	0.0423 (18)	0.0429 (16)	−0.0023 (14)	−0.0016 (12)	0.0036 (13)
C8	0.0639 (19)	0.0420 (18)	0.0384 (15)	0.0004 (14)	−0.0047 (13)	0.0029 (13)
C9	0.0582 (18)	0.0476 (18)	0.0396 (15)	0.0023 (14)	−0.0015 (14)	0.0062 (14)
C10	0.0518 (17)	0.0342 (16)	0.0382 (14)	0.0054 (12)	−0.0003 (12)	0.0064 (12)
C11	0.0500 (17)	0.0415 (16)	0.0396 (14)	0.0085 (13)	0.0038 (12)	0.0040 (13)
C12	0.084 (2)	0.0536 (19)	0.0449 (16)	0.0124 (16)	−0.0011 (15)	0.0121 (14)
C13	0.0527 (17)	0.0402 (17)	0.0376 (15)	0.0000 (13)	0.0006 (12)	0.0106 (12)
C14	0.0451 (16)	0.0408 (17)	0.0432 (15)	0.0011 (13)	0.0023 (12)	0.0023 (13)
C15	0.073 (2)	0.0519 (19)	0.0524 (17)	−0.0011 (16)	0.0008 (15)	−0.0062 (14)

S1—C11	1.716 (3)	C10—C13	1.431 (3)
S1—C14	1.723 (2)	C11—C12	1.502 (3)
O1—N1	1.215 (4)	C13—C14	1.341 (4)
O2—N1	1.221 (4)	C14—C15	1.497 (4)
O3—C9	1.223 (3)	C2—H2	0.9300
N1—C3	1.473 (3)	C4—H4	0.9300
C1—C2	1.398 (3)	C5—H5	0.9300
C1—C6	1.385 (4)	C6—H6	0.9300
C1—C7	1.460 (4)	C7—H7	0.9300
C2—C3	1.369 (4)	C8—H8	0.9300
C3—C4	1.367 (4)	C12—H12A	0.9600
C4—C5	1.368 (4)	C12—H12B	0.9600
C5—C6	1.383 (4)	C12—H12C	0.9600
C7—C8	1.319 (4)	C13—H13	0.9300
C8—C9	1.481 (4)	C15—H15A	0.9600
C9—C10	1.470 (4)	C15—H15B	0.9600
C10—C11	1.370 (3)	C15—H15C	0.9600
C11—S1—C14	93.33 (12)	C13—C14—C15	129.3 (2)
O1—N1—O2	123.4 (2)	C1—C2—H2	120.00
O1—N1—C3	118.7 (2)	C3—C2—H2	120.00
O2—N1—C3	118.0 (2)	C3—C4—H4	121.00
C2—C1—C6	118.1 (2)	C5—C4—H4	121.00
C2—C1—C7	122.8 (2)	C4—C5—H5	120.00
C6—C1—C7	119.2 (2)	C6—C5—H5	120.00
C1—C2—C3	119.1 (2)	C1—C6—H6	119.00
N1—C3—C2	118.7 (2)	C5—C6—H6	119.00
N1—C3—C4	118.7 (2)	C1—C7—H7	115.00
C2—C3—C4	122.7 (2)	C8—C7—H7	115.00
C3—C4—C5	118.8 (3)	C7—C8—H8	119.00
C4—C5—C6	119.9 (3)	C9—C8—H8	119.00
C1—C6—C5	121.5 (2)	C11—C12—H12A	109.00
C1—C7—C8	130.0 (2)	C11—C12—H12B	109.00
C7—C8—C9	121.1 (2)	C11—C12—H12C	109.00
O3—C9—C8	119.3 (2)	H12A—C12—H12B	109.00
O3—C9—C10	121.7 (2)	H12A—C12—H12C	109.00
C8—C9—C10	119.0 (2)	H12B—C12—H12C	109.00
C9—C10—C11	122.7 (2)	C10—C13—H13	123.00
C9—C10—C13	125.7 (2)	C14—C13—H13	123.00
C11—C10—C13	111.7 (2)	C14—C15—H15A	110.00
S1—C11—C10	110.48 (18)	C14—C15—H15B	109.00
S1—C11—C12	119.47 (19)	C14—C15—H15C	109.00
C10—C11—C12	130.0 (2)	H15A—C15—H15B	110.00
C10—C13—C14	114.9 (2)	H15A—C15—H15C	109.00
S1—C14—C13	109.66 (18)	H15B—C15—H15C	109.00
S1—C14—C15	121.10 (19)
C14—S1—C11—C10	−0.85 (19)	C3—C4—C5—C6	−0.4 (4)
C14—S1—C11—C12	−179.6 (2)	C4—C5—C6—C1	0.9 (4)
C11—S1—C14—C13	1.22 (19)	C1—C7—C8—C9	−179.2 (2)
C11—S1—C14—C15	−178.9 (2)	C7—C8—C9—O3	3.8 (4)
O1—N1—C3—C2	7.8 (3)	C7—C8—C9—C10	−175.7 (2)
O1—N1—C3—C4	−171.9 (2)	O3—C9—C10—C11	−14.6 (4)
O2—N1—C3—C2	−171.3 (2)	O3—C9—C10—C13	164.2 (3)
O2—N1—C3—C4	9.0 (3)	C8—C9—C10—C11	164.9 (2)
C6—C1—C2—C3	0.5 (3)	C8—C9—C10—C13	−16.3 (4)
C7—C1—C2—C3	179.9 (2)	C9—C10—C11—S1	179.2 (2)
C2—C1—C6—C5	−0.9 (4)	C9—C10—C11—C12	−2.3 (4)
C7—C1—C6—C5	179.6 (2)	C13—C10—C11—S1	0.3 (2)
C2—C1—C7—C8	7.4 (4)	C13—C10—C11—C12	178.8 (2)
C6—C1—C7—C8	−173.2 (3)	C9—C10—C13—C14	−178.2 (2)
C1—C2—C3—N1	−179.7 (2)	C11—C10—C13—C14	0.7 (3)
C1—C2—C3—C4	0.0 (4)	C10—C13—C14—S1	−1.3 (3)
N1—C3—C4—C5	179.6 (2)	C10—C13—C14—C15	178.9 (2)
C2—C3—C4—C5	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3i	0.93	2.46	3.373 (3)	168
C15—H15B···O2ii	0.96	2.59	3.339 (4)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3i	0.93	2.46	3.373 (3)	168
C15—H15B⋯O2ii	0.96	2.59	3.339 (4)	135

Symmetry codes: (i) ; (ii) .