(2E,4E)-Ethyl 5-(phenyl-sulfon-yl)penta-2,4-dienoate.

In the title compound, C(13)H(14)O(4)S, both C=C double bonds adopt an E conformation. In the crystal, mol-ecules are linked into centrosymmetric R(2) (2)(14) dimers via pairs of C-H⋯O hydrogen bonds.

Related literature

For the biological activity of phenyl sulfonyl-containing compounds see: De-Benedetti et al. (1985 ▶). For a related structure, see: Li (2011 ▶).

Experimental

Crystal data

C13H14O4S

M = 266.30

Triclinic,

a = 6.2525 (3) Å

b = 7.8889 (4) Å

c = 14.5049 (7) Å

α = 82.828 (3)°

β = 87.261 (2)°

γ = 72.426 (2)°

V = 676.69 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 298 K

0.45 × 0.38 × 0.15 mm

Data collection

Bruker APEXII KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.899, T max = 0.965

8948 measured reflections

3084 independent reflections

2621 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.147

S = 1.87

3084 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009907/bt5831sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009907/bt5831Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009907/bt5831Isup3.cml

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

C13H14O4S	Z = 2
Mr = 266.30	F(000) = 280
Triclinic, P1	Dx = 1.307 Mg m−3
a = 6.2525 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8889 (4) Å	Cell parameters from 5946 reflections
c = 14.5049 (7) Å	θ = 2.7–28.3°
α = 82.828 (3)°	µ = 0.24 mm−1
β = 87.261 (2)°	T = 298 K
γ = 72.426 (2)°	Triclinic, colourless
V = 676.69 (6) Å3	0.45 × 0.38 × 0.15 mm

Bruker APEXII KappaCCD diffractometer	3084 independent reflections
Radiation source: fine-focus sealed tube	2621 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 15.9948 pixels mm-1	θmax = 28.4°, θmin = 2.7°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −10→9
Tmin = 0.899, Tmax = 0.965	l = −19→19
8948 measured reflections

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0551P)2] where P = (Fo2 + 2Fc2)/3
S = 1.87	(Δ/σ)max = 0.001
3084 reflections	Δρmax = 0.29 e Å−3
164 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0173 (18)

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	1.5671 (3)	−0.0639 (2)	0.13787 (12)	0.0577 (4)
H1	1.6549	−0.0001	0.1586	0.069*
C2	1.6638 (3)	−0.2359 (3)	0.11608 (12)	0.0670 (5)
H2	1.8179	−0.2881	0.1219	0.080*
C3	1.5361 (3)	−0.3300 (2)	0.08618 (12)	0.0634 (5)
H3	1.6035	−0.4465	0.0726	0.076*
C4	1.3103 (3)	−0.2555 (3)	0.07586 (14)	0.0714 (5)
H4	1.2246	−0.3206	0.0549	0.086*
C5	1.2088 (3)	−0.0820 (2)	0.09680 (12)	0.0612 (4)
H5	1.0550	−0.0299	0.0895	0.073*
C6	1.3387 (2)	0.0124 (2)	0.12854 (9)	0.0446 (3)
C7	1.0978 (3)	0.1812 (2)	0.27041 (10)	0.0534 (4)
H7	1.1952	0.1132	0.3169	0.064*
C8	0.8815 (3)	0.2378 (2)	0.29034 (11)	0.0545 (4)
H8	0.7812	0.3023	0.2441	0.065*
C9	0.7980 (3)	0.2008 (2)	0.38347 (11)	0.0585 (4)
H9	0.9013	0.1296	0.4271	0.070*
C10	0.5861 (3)	0.2604 (2)	0.41125 (11)	0.0603 (4)
H10	0.4768	0.3307	0.3697	0.072*
C11	0.5253 (3)	0.2140 (3)	0.50916 (12)	0.0616 (4)
C12	0.2457 (4)	0.2713 (3)	0.62613 (15)	0.0902 (7)
H12A	0.2830	0.1440	0.6466	0.108*
H12B	0.3229	0.3242	0.6655	0.108*
C13	0.0051 (4)	0.3538 (4)	0.63268 (17)	0.1022 (8)
H13A	−0.0313	0.4779	0.6084	0.153*
H13B	−0.0420	0.3436	0.6966	0.153*
H13C	−0.0704	0.2944	0.5974	0.153*
O1	1.0292 (2)	0.32081 (16)	0.09966 (8)	0.0719 (4)
O2	1.3810 (2)	0.30846 (17)	0.17469 (9)	0.0749 (4)
O3	0.6500 (2)	0.1095 (2)	0.56403 (9)	0.0889 (5)
O4	0.3154 (2)	0.3006 (2)	0.52876 (8)	0.0778 (4)
S1	1.20983 (6)	0.22766 (5)	0.16117 (3)	0.05254 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0426 (8)	0.0583 (10)	0.0721 (10)	−0.0123 (7)	0.0000 (7)	−0.0144 (8)
C2	0.0466 (9)	0.0661 (12)	0.0762 (11)	0.0015 (8)	0.0056 (8)	−0.0106 (9)
C3	0.0706 (11)	0.0474 (9)	0.0635 (9)	−0.0046 (8)	0.0109 (8)	−0.0111 (7)
C4	0.0729 (12)	0.0618 (12)	0.0873 (12)	−0.0260 (10)	0.0008 (10)	−0.0236 (10)
C5	0.0462 (8)	0.0578 (10)	0.0782 (11)	−0.0109 (8)	−0.0021 (8)	−0.0140 (8)
C6	0.0428 (7)	0.0419 (8)	0.0454 (7)	−0.0087 (6)	0.0009 (6)	−0.0020 (6)
C7	0.0576 (9)	0.0475 (9)	0.0494 (8)	−0.0075 (7)	−0.0029 (7)	−0.0041 (6)
C8	0.0565 (9)	0.0496 (9)	0.0516 (8)	−0.0064 (7)	−0.0025 (7)	−0.0074 (7)
C9	0.0590 (10)	0.0562 (10)	0.0548 (9)	−0.0099 (8)	−0.0007 (7)	−0.0047 (7)
C10	0.0572 (10)	0.0603 (11)	0.0552 (9)	−0.0060 (8)	−0.0003 (7)	−0.0046 (8)
C11	0.0595 (10)	0.0586 (11)	0.0615 (10)	−0.0110 (8)	0.0010 (8)	−0.0047 (8)
C12	0.0948 (15)	0.0925 (16)	0.0674 (11)	−0.0119 (13)	0.0204 (11)	0.0019 (11)
C13	0.0908 (16)	0.122 (2)	0.0886 (15)	−0.0233 (15)	0.0273 (13)	−0.0240 (15)
O1	0.0726 (8)	0.0597 (8)	0.0600 (7)	0.0108 (6)	−0.0020 (6)	0.0051 (5)
O2	0.0824 (9)	0.0565 (8)	0.0942 (9)	−0.0331 (7)	0.0119 (7)	−0.0141 (7)
O3	0.0740 (9)	0.1009 (12)	0.0691 (8)	−0.0048 (8)	−0.0020 (7)	0.0225 (7)
O4	0.0705 (8)	0.0792 (10)	0.0640 (7)	0.0013 (7)	0.0155 (6)	0.0001 (7)
S1	0.0557 (3)	0.0399 (3)	0.0553 (3)	−0.00635 (19)	0.00194 (18)	−0.00117 (17)

C1—C2	1.378 (2)	C8—H8	0.9300
C1—C6	1.378 (2)	C9—C10	1.326 (2)
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.359 (2)	C10—C11	1.483 (2)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.363 (3)	C11—O3	1.195 (2)
C3—H3	0.9300	C11—O4	1.319 (2)
C4—C5	1.389 (3)	C12—C13	1.451 (3)
C4—H4	0.9300	C12—O4	1.469 (2)
C5—C6	1.383 (2)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—S1	1.7595 (15)	C13—H13A	0.9600
C7—C8	1.320 (2)	C13—H13B	0.9600
C7—S1	1.7434 (15)	C13—H13C	0.9600
C7—H7	0.9300	O1—S1	1.4294 (12)
C8—C9	1.452 (2)	O2—S1	1.4328 (13)
C2—C1—C6	119.12 (15)	C8—C9—H9	117.4
C2—C1—H1	120.4	C9—C10—C11	119.36 (17)
C6—C1—H1	120.4	C9—C10—H10	120.3
C3—C2—C1	120.67 (15)	C11—C10—H10	120.3
C3—C2—H2	119.7	O3—C11—O4	123.62 (16)
C1—C2—H2	119.7	O3—C11—C10	124.36 (17)
C2—C3—C4	120.76 (17)	O4—C11—C10	112.01 (15)
C2—C3—H3	119.6	C13—C12—O4	108.24 (19)
C4—C3—H3	119.6	C13—C12—H12A	110.1
C3—C4—C5	119.78 (17)	O4—C12—H12A	110.1
C3—C4—H4	120.1	C13—C12—H12B	110.1
C5—C4—H4	120.1	O4—C12—H12B	110.1
C6—C5—C4	119.32 (16)	H12A—C12—H12B	108.4
C6—C5—H5	120.3	C12—C13—H13A	109.5
C4—C5—H5	120.3	C12—C13—H13B	109.5
C1—C6—C5	120.34 (15)	H13A—C13—H13B	109.5
C1—C6—S1	119.90 (12)	C12—C13—H13C	109.5
C5—C6—S1	119.71 (11)	H13A—C13—H13C	109.5
C8—C7—S1	123.19 (13)	H13B—C13—H13C	109.5
C8—C7—H7	118.4	C11—O4—C12	115.52 (15)
S1—C7—H7	118.4	O1—S1—O2	119.36 (8)
C7—C8—C9	120.95 (15)	O1—S1—C7	108.53 (8)
C7—C8—H8	119.5	O2—S1—C7	107.09 (8)
C9—C8—H8	119.5	O1—S1—C6	109.53 (7)
C10—C9—C8	125.22 (16)	O2—S1—C6	108.57 (7)
C10—C9—H9	117.4	C7—S1—C6	102.40 (7)
C6—C1—C2—C3	−0.3 (3)	O3—C11—O4—C12	4.5 (3)
C1—C2—C3—C4	0.9 (3)	C10—C11—O4—C12	−176.12 (16)
C2—C3—C4—C5	−0.5 (3)	C13—C12—O4—C11	−171.7 (2)
C3—C4—C5—C6	−0.4 (3)	C8—C7—S1—O1	−4.46 (18)
C2—C1—C6—C5	−0.7 (2)	C8—C7—S1—O2	125.64 (16)
C2—C1—C6—S1	176.98 (12)	C8—C7—S1—C6	−120.23 (16)
C4—C5—C6—C1	1.0 (2)	C1—C6—S1—O1	144.75 (14)
C4—C5—C6—S1	−176.61 (14)	C5—C6—S1—O1	−37.59 (14)
S1—C7—C8—C9	−177.71 (12)	C1—C6—S1—O2	12.83 (15)
C7—C8—C9—C10	176.02 (18)	C5—C6—S1—O2	−169.51 (12)
C8—C9—C10—C11	−179.12 (15)	C1—C6—S1—C7	−100.21 (14)
C9—C10—C11—O3	−8.3 (3)	C5—C6—S1—C7	77.46 (14)
C9—C10—C11—O4	172.26 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3i	0.93	2.32	3.212 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3i	0.93	2.32	3.212 (2)	161

Symmetry code: (i) .