Ethyl (2E,4E)-5-(3-bromo-phenyl-sulfon-yl)penta-2,4-dienoate.

In the title compound, C13H13BrO4S, both C=C double bonds adopt an E conformation. The S atom has a distorted tetra-hedral geometry with bond angles ranging from 102.17 (13) to 119.77 (14)°. The ethyl acrylate substituent adopts an extented conformation with all torsion angles close to 180°. 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 ▶); Chumakov et al. (2006 ▶); Kremer et al. (2006 ▶). For related structures, see: Li et al. (2011 ▶); Sankar et al. (2012 ▶); Chakkaravarthi et al. (2008 ▶); Rodriguez et al. (1995 ▶). For graph-set analysis of hydrogen bonds, see: Sankar et al. (2012 ▶).

Experimental

Crystal data

C13H13BrO4S

M = 345.20

Monoclinic,

a = 27.883 (5) Å

b = 6.001 (5) Å

c = 17.256 (5) Å

β = 94.020 (5)°

V = 2880 (3) Å3

Z = 8

Mo Kα radiation

μ = 3.01 mm−1

T = 293 K

0.32 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.972, T max = 0.992

14906 measured reflections

3479 independent reflections

2360 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.01

3479 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.41 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005771/bt6881sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005771/bt6881Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005771/bt6881Isup3.cml

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

C13H13BrO4S	F(000) = 1392
Mr = 345.20	Dx = 1.592 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5710 reflections
a = 27.883 (5) Å	θ = 1.8–28.5°
b = 6.001 (5) Å	µ = 3.01 mm−1
c = 17.256 (5) Å	T = 293 K
β = 94.020 (5)°	Monoclinic, colourless
V = 2880 (3) Å3	0.32 × 0.20 × 0.10 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	3479 independent reflections
Radiation source: fine-focus sealed tube	2360 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω and φ scans	θmax = 28.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −35→36
Tmin = 0.972, Tmax = 0.992	k = −7→7
14906 measured reflections	l = −22→22

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.4368P] where P = (Fo2 + 2Fc2)/3
3479 reflections	(Δ/σ)max = 0.006
172 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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
Br1	0.826326 (13)	0.42424 (6)	0.247333 (16)	0.06505 (16)
S1	0.83626 (3)	0.20959 (12)	−0.06349 (4)	0.0457 (2)
O1	0.84030 (9)	0.4471 (3)	−0.06892 (12)	0.0624 (6)
O2	0.80643 (9)	0.0904 (4)	−0.12028 (12)	0.0616 (6)
O3	1.04522 (10)	−0.3791 (5)	−0.07427 (19)	0.0914 (9)
C7	0.89422 (11)	0.0998 (5)	−0.05976 (16)	0.0494 (7)
H7	0.9190	0.1778	−0.0331	0.059*
O4	1.01637 (8)	−0.6642 (5)	−0.14354 (16)	0.0839 (8)
C10	0.96335 (12)	−0.3814 (6)	−0.1170 (2)	0.0589 (8)
H10	0.9396	−0.4653	−0.1438	0.071*
C5	0.81767 (9)	0.1422 (4)	0.02920 (14)	0.0398 (6)
C6	0.82704 (9)	0.2916 (4)	0.08969 (13)	0.0411 (6)
H6	0.8414	0.4286	0.0815	0.049*
C4	0.79667 (11)	−0.0622 (5)	0.04048 (17)	0.0520 (7)
H4	0.7913	−0.1616	−0.0006	0.062*
C8	0.90412 (11)	−0.0915 (5)	−0.09374 (16)	0.0484 (7)
H8	0.8795	−0.1664	−0.1220	0.058*
C11	1.01207 (12)	−0.4709 (6)	−0.10820 (18)	0.0582 (8)
C2	0.79283 (10)	0.0286 (5)	0.17491 (17)	0.0507 (7)
H2	0.7845	−0.0094	0.2245	0.061*
C1	0.81425 (10)	0.2298 (5)	0.16221 (14)	0.0428 (6)
C3	0.78369 (12)	−0.1169 (6)	0.11396 (18)	0.0585 (8)
H3	0.7687	−0.2524	0.1223	0.070*
C9	0.95162 (11)	−0.1879 (5)	−0.08865 (16)	0.0538 (8)
H9	0.9761	−0.1053	−0.0630	0.065*
C12	1.06419 (14)	−0.7664 (9)	−0.1426 (3)	0.0987 (14)
H12A	1.0883	−0.6510	−0.1460	0.118*
H12B	1.0709	−0.8463	−0.0942	0.118*
C13	1.06654 (17)	−0.9140 (9)	−0.2053 (3)	0.1135 (18)
H13B	1.0979	−0.9801	−0.2039	0.170*
H13A	1.0605	−0.8342	−0.2532	0.170*
H13C	1.0428	−1.0288	−0.2017	0.170*

	U11	U22	U33	U12	U13	U23
Br1	0.0838 (3)	0.0745 (3)	0.03659 (18)	0.00982 (17)	0.00276 (15)	−0.01125 (13)
S1	0.0591 (5)	0.0479 (4)	0.0299 (3)	−0.0021 (3)	0.0025 (3)	0.0021 (3)
O1	0.0920 (17)	0.0469 (13)	0.0493 (12)	0.0012 (11)	0.0120 (11)	0.0132 (9)
O2	0.0664 (14)	0.0790 (16)	0.0375 (10)	−0.0003 (11)	−0.0098 (9)	−0.0063 (9)
O3	0.0638 (17)	0.102 (2)	0.105 (2)	−0.0017 (15)	−0.0198 (15)	−0.0347 (17)
C7	0.0517 (18)	0.0586 (19)	0.0382 (14)	−0.0134 (14)	0.0044 (12)	−0.0030 (12)
O4	0.0497 (14)	0.0894 (18)	0.110 (2)	0.0094 (13)	−0.0102 (13)	−0.0372 (16)
C10	0.0491 (19)	0.064 (2)	0.0635 (19)	−0.0077 (15)	0.0030 (15)	−0.0109 (15)
C5	0.0440 (15)	0.0432 (14)	0.0321 (12)	−0.0003 (12)	0.0023 (11)	0.0022 (10)
C6	0.0452 (16)	0.0418 (15)	0.0364 (13)	−0.0002 (12)	0.0035 (11)	0.0002 (11)
C4	0.0541 (19)	0.0563 (19)	0.0453 (15)	−0.0129 (14)	0.0024 (13)	−0.0016 (13)
C8	0.0542 (18)	0.0529 (17)	0.0386 (14)	−0.0084 (14)	0.0065 (12)	−0.0040 (12)
C11	0.052 (2)	0.070 (2)	0.0517 (17)	−0.0072 (16)	0.0005 (15)	−0.0075 (15)
C2	0.0421 (17)	0.068 (2)	0.0425 (15)	0.0031 (14)	0.0089 (12)	0.0115 (13)
C1	0.0410 (15)	0.0531 (16)	0.0341 (12)	0.0095 (13)	0.0009 (11)	−0.0028 (11)
C3	0.059 (2)	0.063 (2)	0.0539 (18)	−0.0192 (16)	0.0038 (15)	0.0145 (14)
C9	0.0539 (19)	0.062 (2)	0.0456 (15)	−0.0123 (15)	0.0076 (13)	−0.0103 (14)
C12	0.053 (2)	0.134 (4)	0.107 (3)	0.027 (2)	−0.012 (2)	−0.035 (3)
C13	0.081 (3)	0.139 (5)	0.121 (4)	0.045 (3)	0.013 (3)	−0.007 (3)

Br1—C1	1.888 (3)	C6—H6	0.9300
S1—O2	1.431 (2)	C4—C3	1.382 (4)
S1—O1	1.433 (2)	C4—H4	0.9300
S1—C7	1.742 (3)	C8—C9	1.442 (4)
S1—C5	1.763 (2)	C8—H8	0.9300
O3—C11	1.193 (4)	C2—C1	1.371 (4)
C7—C8	1.327 (4)	C2—C3	1.377 (5)
C7—H7	0.9300	C2—H2	0.9300
O4—C11	1.320 (4)	C3—H3	0.9300
O4—C12	1.467 (4)	C9—H9	0.9300
C10—C9	1.310 (5)	C12—C13	1.403 (6)
C10—C11	1.459 (5)	C12—H12A	0.9700
C10—H10	0.9300	C12—H12B	0.9700
C5—C4	1.379 (4)	C13—H13B	0.9600
C5—C6	1.387 (3)	C13—H13A	0.9600
C6—C1	1.376 (3)	C13—H13C	0.9600
O2—S1—O1	119.77 (14)	O3—C11—C10	124.4 (3)
O2—S1—C7	109.23 (14)	O4—C11—C10	112.9 (3)
O1—S1—C7	107.56 (15)	C1—C2—C3	119.7 (3)
O2—S1—C5	108.23 (13)	C1—C2—H2	120.2
O1—S1—C5	108.47 (13)	C3—C2—H2	120.2
C7—S1—C5	102.17 (13)	C2—C1—C6	121.8 (2)
C8—C7—S1	122.1 (2)	C2—C1—Br1	118.4 (2)
C8—C7—H7	118.9	C6—C1—Br1	119.8 (2)
S1—C7—H7	118.9	C2—C3—C4	120.3 (3)
C11—O4—C12	118.3 (3)	C2—C3—H3	119.9
C9—C10—C11	122.9 (3)	C4—C3—H3	119.9
C9—C10—H10	118.6	C10—C9—C8	125.8 (3)
C11—C10—H10	118.6	C10—C9—H9	117.1
C4—C5—C6	121.9 (2)	C8—C9—H9	117.1
C4—C5—S1	119.1 (2)	C13—C12—O4	110.3 (3)
C6—C5—S1	118.9 (2)	C13—C12—H12A	109.6
C1—C6—C5	117.6 (2)	O4—C12—H12A	109.6
C1—C6—H6	121.2	C13—C12—H12B	109.6
C5—C6—H6	121.2	O4—C12—H12B	109.6
C5—C4—C3	118.8 (3)	H12A—C12—H12B	108.1
C5—C4—H4	120.6	C12—C13—H13B	109.5
C3—C4—H4	120.6	C12—C13—H13A	109.5
C7—C8—C9	122.6 (3)	H13B—C13—H13A	109.5
C7—C8—H8	118.7	C12—C13—H13C	109.5
C9—C8—H8	118.7	H13B—C13—H13C	109.5
O3—C11—O4	122.7 (3)	H13A—C13—H13C	109.5
O2—S1—C7—C8	−12.3 (3)	C12—O4—C11—O3	−1.7 (6)
O1—S1—C7—C8	−143.8 (2)	C12—O4—C11—C10	176.8 (4)
C5—S1—C7—C8	102.1 (3)	C9—C10—C11—O3	0.8 (6)
O2—S1—C5—C4	28.0 (3)	C9—C10—C11—O4	−177.7 (3)
O1—S1—C5—C4	159.4 (2)	C3—C2—C1—C6	0.0 (4)
C7—S1—C5—C4	−87.1 (3)	C3—C2—C1—Br1	−179.8 (2)
O2—S1—C5—C6	−155.5 (2)	C5—C6—C1—C2	−0.2 (4)
O1—S1—C5—C6	−24.1 (3)	C5—C6—C1—Br1	179.61 (19)
C7—S1—C5—C6	89.3 (2)	C1—C2—C3—C4	1.0 (5)
C4—C5—C6—C1	−0.5 (4)	C5—C4—C3—C2	−1.7 (5)
S1—C5—C6—C1	−176.9 (2)	C11—C10—C9—C8	−178.6 (3)
C6—C5—C4—C3	1.5 (5)	C7—C8—C9—C10	176.0 (3)
S1—C5—C4—C3	177.8 (2)	C11—O4—C12—C13	−156.5 (4)
S1—C7—C8—C9	−177.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3i	0.93	2.37	3.235 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3i	0.93	2.37	3.235 (4)	154

Symmetry code: (i) .