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

In the title compound, C13H12Cl2O4S, both C=C double bonds adopt an E conformation. The S atom has a distorted tetra-hedral geometry with bond angles ranging from 103.03 (12) to 118.12 (13)°. The eth-oxy-carbonyl group is disordered over two sets of sites, with site-occupancy factors of 0.739 (11) and 0.261 (11). In the crystal, C-H⋯O inter-actions link the mol-ecules into chains mol-ecules running parallel to the a axis.

Related literature

For the biological activity of phenyl­sulfonyl-containing compounds, see: De Benedetti et al. (1985 ▶). For related structures, see: Li (2011 ▶); Sankar et al. (2012 ▶); Chakkaravarthi et al. (2008 ▶); Rodriguez et al. (1995 ▶).

Experimental

Crystal data

C13H12Cl2O4S

M = 335.19

Monoclinic,

a = 5.773 (5) Å

b = 9.939 (5) Å

c = 13.268 (5) Å

β = 95.876 (5)°

V = 757.3 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.57 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.824, T max = 0.847

6848 measured reflections

2471 independent reflections

2314 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.074

S = 1.06

2471 reflections

209 parameters

74 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1054 Friedel pairs

Absolute structure parameter: 0.04 (6)

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813021429/pv2638sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021429/pv2638Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021429/pv2638Isup3.cml

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

C13H12Cl2O4S	F(000) = 344
Mr = 335.19	Dx = 1.470 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8834 reflections
a = 5.773 (5) Å	θ = 2.1–31.2°
b = 9.939 (5) Å	µ = 0.57 mm−1
c = 13.268 (5) Å	T = 293 K
β = 95.876 (5)°	Block, colourless
V = 757.3 (8) Å3	0.30 × 0.30 × 0.20 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	2471 independent reflections
Radiation source: fine-focus sealed tube	2314 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω and φ scan	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→6
Tmin = 0.824, Tmax = 0.847	k = −11→8
6848 measured reflections	l = −15→15

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0288P)2 + 0.2277P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2471 reflections	Δρmax = 0.24 e Å−3
209 parameters	Δρmin = −0.21 e Å−3
74 restraints	Absolute structure: Flack (1983), 1054 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (6)

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)
C1	0.5395 (4)	0.2357 (3)	0.6203 (2)	0.0521 (6)
C2	0.5786 (6)	0.1770 (3)	0.7135 (2)	0.0667 (8)
H2	0.7097	0.1991	0.7571	0.080*
C3	0.4218 (6)	0.0853 (4)	0.7415 (2)	0.0741 (9)
C4	0.2235 (6)	0.0511 (3)	0.6808 (2)	0.0714 (8)
H4	0.1171	−0.0097	0.7028	0.086*
C5	0.1869 (5)	0.1095 (3)	0.5862 (2)	0.0597 (7)
H5	0.0561	0.0859	0.5430	0.072*
C6	0.3436 (4)	0.2036 (3)	0.5546 (2)	0.0486 (6)
C7	0.5117 (4)	0.2097 (3)	0.3680 (2)	0.0530 (6)
H7	0.6635	0.2387	0.3858	0.064*
C8	0.4707 (4)	0.1217 (3)	0.2951 (2)	0.0518 (6)
H8	0.3172	0.0981	0.2747	0.062*
C9	0.6546 (4)	0.0595 (3)	0.24492 (19)	0.0536 (6)
H9	0.8072	0.0847	0.2656	0.064*
C10	0.6203 (5)	−0.0303 (3)	0.1722 (2)	0.0577 (7)
H10	0.4687	−0.0534	0.1478	0.069*
C11	0.8169 (6)	−0.0953 (4)	0.1282 (2)	0.0722 (9)
O1	0.0716 (3)	0.2181 (2)	0.38846 (15)	0.0669 (6)
O2	0.3050 (4)	0.4175 (2)	0.43995 (17)	0.0713 (6)
O3	1.0171 (4)	−0.0764 (4)	0.1560 (2)	0.1189 (12)
Cl1	0.4769 (3)	0.00684 (14)	0.85912 (9)	0.1250 (5)
Cl2	0.74573 (11)	0.35013 (8)	0.58707 (6)	0.0671 (2)
S1	0.28638 (10)	0.27417 (7)	0.43281 (5)	0.05173 (18)
O4	0.7333 (12)	−0.1885 (7)	0.0550 (6)	0.0776 (16)	0.739 (11)
C12	0.9044 (15)	−0.2721 (8)	0.0100 (6)	0.103 (2)	0.739 (11)
H12A	1.0289	−0.2963	0.0615	0.124*	0.739 (11)
H12B	0.8306	−0.3543	−0.0164	0.124*	0.739 (11)
C13	0.9999 (15)	−0.2001 (9)	−0.0710 (7)	0.137 (3)	0.739 (11)
H13A	1.1127	−0.2556	−0.0995	0.205*	0.739 (11)
H13B	1.0734	−0.1190	−0.0447	0.205*	0.739 (11)
H13C	0.8769	−0.1779	−0.1226	0.205*	0.739 (11)
O4'	0.777 (3)	−0.1422 (19)	0.0509 (18)	0.079 (4)	0.261 (11)
C12'	0.966 (3)	−0.205 (2)	0.0030 (17)	0.094 (5)	0.261 (11)
H12C	1.0634	−0.2571	0.0525	0.113*	0.261 (11)
H12D	1.0614	−0.1365	−0.0244	0.113*	0.261 (11)
C13'	0.865 (4)	−0.293 (2)	−0.0783 (15)	0.125 (7)	0.261 (11)
H13D	0.9866	−0.3274	−0.1152	0.188*	0.261 (11)
H13E	0.7566	−0.2425	−0.1233	0.188*	0.261 (11)
H13F	0.7854	−0.3662	−0.0498	0.188*	0.261 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0450 (13)	0.0456 (16)	0.0666 (17)	0.0056 (10)	0.0099 (11)	−0.0127 (12)
C2	0.0668 (19)	0.067 (2)	0.0655 (19)	0.0109 (16)	0.0055 (15)	−0.0085 (15)
C3	0.091 (2)	0.067 (2)	0.067 (2)	0.020 (2)	0.0172 (17)	0.0022 (17)
C4	0.075 (2)	0.0610 (19)	0.084 (2)	0.0022 (17)	0.0347 (17)	0.0024 (18)
C5	0.0443 (14)	0.0577 (19)	0.080 (2)	−0.0016 (11)	0.0208 (13)	−0.0074 (15)
C6	0.0369 (12)	0.0445 (14)	0.0659 (16)	0.0061 (11)	0.0119 (11)	−0.0089 (12)
C7	0.0330 (12)	0.0651 (18)	0.0621 (16)	−0.0004 (11)	0.0112 (11)	−0.0003 (14)
C8	0.0345 (12)	0.0667 (17)	0.0549 (15)	−0.0035 (11)	0.0075 (11)	0.0052 (13)
C9	0.0401 (12)	0.0696 (18)	0.0526 (14)	0.0002 (14)	0.0119 (10)	0.0025 (15)
C10	0.0445 (14)	0.0692 (19)	0.0602 (16)	0.0018 (12)	0.0088 (12)	0.0036 (15)
C11	0.0620 (19)	0.096 (3)	0.0594 (17)	0.0193 (17)	0.0110 (15)	−0.0055 (17)
O1	0.0306 (8)	0.0966 (16)	0.0740 (13)	0.0012 (9)	0.0072 (8)	−0.0091 (11)
O2	0.0631 (12)	0.0541 (13)	0.0978 (16)	0.0121 (11)	0.0133 (11)	0.0071 (12)
O3	0.0513 (14)	0.201 (3)	0.1044 (19)	0.0282 (17)	0.0099 (13)	−0.048 (2)
Cl1	0.1582 (11)	0.1325 (11)	0.0856 (7)	0.0214 (8)	0.0194 (7)	0.0369 (6)
Cl2	0.0490 (4)	0.0649 (4)	0.0873 (5)	−0.0096 (4)	0.0072 (3)	−0.0181 (4)
S1	0.0318 (3)	0.0585 (4)	0.0656 (4)	0.0040 (3)	0.0089 (2)	−0.0020 (4)
O4	0.079 (3)	0.069 (4)	0.088 (2)	−0.002 (2)	0.024 (2)	−0.027 (3)
C12	0.120 (5)	0.084 (5)	0.111 (5)	0.001 (4)	0.036 (4)	−0.033 (4)
C13	0.148 (7)	0.119 (7)	0.157 (7)	0.014 (5)	0.081 (6)	−0.010 (5)
O4'	0.084 (8)	0.062 (9)	0.090 (7)	−0.001 (6)	0.004 (6)	−0.031 (7)
C12'	0.105 (9)	0.089 (10)	0.095 (8)	−0.003 (8)	0.041 (8)	−0.039 (8)
C13'	0.164 (15)	0.109 (14)	0.104 (12)	0.009 (12)	0.019 (11)	−0.054 (11)

C1—C2	1.366 (4)	C10—H10	0.9300
C1—C6	1.393 (4)	C11—O4'	1.13 (2)
C1—Cl2	1.735 (3)	C11—O3	1.191 (4)
C2—C3	1.363 (5)	C11—O4	1.392 (8)
C2—H2	0.9300	O1—S1	1.430 (2)
C3—C4	1.373 (5)	O2—S1	1.431 (2)
C3—Cl1	1.744 (3)	O4—C12	1.464 (6)
C4—C5	1.380 (4)	C12—C13	1.447 (9)
C4—H4	0.9300	C12—H12A	0.9700
C5—C6	1.395 (4)	C12—H12B	0.9700
C5—H5	0.9300	C13—H13A	0.9600
C6—S1	1.761 (3)	C13—H13B	0.9600
C7—C8	1.307 (4)	C13—H13C	0.9600
C7—S1	1.752 (3)	O4'—C12'	1.456 (10)
C7—H7	0.9300	C12'—C13'	1.461 (17)
C8—C9	1.449 (4)	C12'—H12C	0.9700
C8—H8	0.9300	C12'—H12D	0.9700
C9—C10	1.315 (4)	C13'—H13D	0.9600
C9—H9	0.9300	C13'—H13E	0.9600
C10—C11	1.477 (4)	C13'—H13F	0.9600
C2—C1—C6	121.1 (3)	O4—C11—C10	109.9 (4)
C2—C1—Cl2	117.1 (2)	O1—S1—O2	118.12 (13)
C6—C1—Cl2	121.7 (2)	O1—S1—C7	108.15 (13)
C3—C2—C1	118.7 (3)	O2—S1—C7	109.99 (13)
C3—C2—H2	120.7	O1—S1—C6	107.18 (12)
C1—C2—H2	120.7	O2—S1—C6	109.29 (14)
C2—C3—C4	122.9 (3)	C7—S1—C6	103.03 (12)
C2—C3—Cl1	118.5 (3)	C11—O4—C12	117.5 (6)
C4—C3—Cl1	118.6 (3)	C13—C12—O4	110.3 (6)
C3—C4—C5	118.0 (3)	C13—C12—H12A	109.6
C3—C4—H4	121.0	O4—C12—H12A	109.6
C5—C4—H4	121.0	C13—C12—H12B	109.6
C4—C5—C6	120.8 (3)	O4—C12—H12B	109.6
C4—C5—H5	119.6	H12A—C12—H12B	108.1
C6—C5—H5	119.6	C12—C13—H13A	109.5
C1—C6—C5	118.4 (3)	C12—C13—H13B	109.5
C1—C6—S1	123.1 (2)	H13A—C13—H13B	109.5
C5—C6—S1	118.5 (2)	C12—C13—H13C	109.5
C8—C7—S1	121.3 (2)	H13A—C13—H13C	109.5
C8—C7—H7	119.3	H13B—C13—H13C	109.5
S1—C7—H7	119.3	C11—O4'—C12'	118.9 (17)
C7—C8—C9	122.7 (2)	O4'—C12'—C13'	108.6 (13)
C7—C8—H8	118.7	O4'—C12'—H12C	110.0
C9—C8—H8	118.7	C13'—C12'—H12C	110.0
C10—C9—C8	124.4 (2)	O4'—C12'—H12D	110.0
C10—C9—H9	117.8	C13'—C12'—H12D	110.0
C8—C9—H9	117.8	H12C—C12'—H12D	108.4
C9—C10—C11	121.5 (3)	C12'—C13'—H13D	109.5
C9—C10—H10	119.2	C12'—C13'—H13E	109.5
C11—C10—H10	119.2	H13D—C13'—H13E	109.5
O4'—C11—O3	116.5 (10)	C12'—C13'—H13F	109.5
O3—C11—O4	125.2 (4)	H13D—C13'—H13F	109.5
O4'—C11—C10	116.6 (10)	H13E—C13'—H13F	109.5
O3—C11—C10	124.7 (3)
C6—C1—C2—C3	0.1 (4)	C9—C10—C11—O4	178.3 (4)
Cl2—C1—C2—C3	−179.1 (2)	C8—C7—S1—O1	−2.3 (3)
C1—C2—C3—C4	−1.2 (5)	C8—C7—S1—O2	−132.6 (2)
C1—C2—C3—Cl1	178.1 (2)	C8—C7—S1—C6	110.9 (3)
C2—C3—C4—C5	2.1 (5)	C1—C6—S1—O1	−179.8 (2)
Cl1—C3—C4—C5	−177.3 (2)	C5—C6—S1—O1	1.1 (2)
C3—C4—C5—C6	−1.8 (4)	C1—C6—S1—O2	−50.6 (2)
C2—C1—C6—C5	0.1 (4)	C5—C6—S1—O2	130.3 (2)
Cl2—C1—C6—C5	179.29 (19)	C1—C6—S1—C7	66.3 (2)
C2—C1—C6—S1	−179.0 (2)	C5—C6—S1—C7	−112.8 (2)
Cl2—C1—C6—S1	0.2 (3)	O4'—C11—O4—C12	73 (3)
C4—C5—C6—C1	0.8 (4)	O3—C11—O4—C12	1.3 (9)
C4—C5—C6—S1	180.0 (2)	C10—C11—O4—C12	−174.4 (5)
S1—C7—C8—C9	−175.6 (2)	C11—O4—C12—C13	−82.9 (10)
C7—C8—C9—C10	179.3 (3)	O3—C11—O4'—C12'	15 (2)
C8—C9—C10—C11	−176.5 (3)	O4—C11—O4'—C12'	−105 (4)
C9—C10—C11—O4'	−159.7 (13)	C10—C11—O4'—C12'	178.7 (15)
C9—C10—C11—O3	2.6 (6)	C11—O4'—C12'—C13'	163 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.36	3.217 (4)	153
C9—H9···O1i	0.93	2.50	3.312 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.36	3.217 (4)	153
C9—H9⋯O1i	0.93	2.50	3.312 (4)	146

Symmetry code: (i) .