Ethyl (2E,4Z)-5-diethyl­amino-2-(phenyl­sulfon­yl)penta-2,4-dienoate

Guo-Qiang Song; Pei-Pei Yu; Xian-Feng Huang

doi:10.1107/S1600536812023483

. 2012 May 31;68(Pt 6):o1919. doi: 10.1107/S1600536812023483

Ethyl (2E,4Z)-5-diethylamino-2-(phenylsulfonyl)penta-2,4-dienoate

Guo-Qiang Song ^a, Pei-Pei Yu ^a, Xian-Feng Huang ^a,^*

PMCID: PMC3379474 PMID: 22719672

Abstract

In the title compound, C₁₇H₂₃NO₄S, the pentadiene group adopts a planar conformation, with an r.m.s. deviation of 0.0410 (14) Å. The phenyl ring makes a dihedral angle of 85.73 (11)° with the pentadiene group, while the pentadiene group makes dihedral angles of 11.38 (11) and 14.08 (10)°, respectively, with the amino and ester groups. In the crystal, molecules are linked via pairs of C—H⋯O interactions, forming inversion dimers.

Related literature

For background information on pentadienoates, see: Sorbetti et al. (2007 ▶). For structural data of pentadienoates, see: Ceard et al. (2002 ▶). For details of weak hydrogen-bonding interactions, see: Steiner (2002 ▶). graphic file with name e-68-o1919-scheme1.jpg

Experimental

Crystal data

C₁₇H₂₃NO₄S
M _r = 337.42
Monoclinic,
a = 14.489 (2) Å
b = 8.2989 (12) Å
c = 16.706 (3) Å
β = 114.313 (3)°
V = 1830.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.669, T _max = 0.746
11618 measured reflections
4183 independent reflections
2977 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.168
S = 1.04
4183 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023483/pk2405sup1.cif

e-68-o1919-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023483/pk2405Isup2.hkl

e-68-o1919-Isup2.hkl^{(205KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812023483/pk2405Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.93	2.41	3.277 (3)	155

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Analogues of pentadienoate have been used widely in perfumes, lubricants, as pharmaceutical intermediates and in other chemical industries (Ceard et al., 2002; Sorbetti et al., 2007). In this work, we report the crystal structure of the title compound, C₁₇H₂₃NO₄S, (I). In the crystal (Fig. 1), the pentadiene group adopts a planar conformation with an r.m.s. deviation of 0.0410 (14) Å. The phenyl ring makes a dihedral angle of 85.73 (11)° with the pentadiene group. The dihedral angle of pentadiene with the amino group (atoms N1, C14, C16) is 11.38 (11)° and the dihedral angle between pentadiene and the ester group (atoms C8, O3, O4) is 14.08 (10)°. The crystal structure exhibits weak intermolecular C—H···O hydrogen bonds (Steiner, 2002; Table 1) between pairs of inversion related (-x, 1-y, 1-z) molecules to produce a weakly hydrogen-bonded dimer as shown in Fig. 2.

Experimental

The title compound was prepared by stirring a mixture of malonaldehyde bis(dimethyl acetal) (411 mg, 2.5 mmol), ethanamine (366 mg, 2.5 mmol) and acetic acid (300 mg, 5 mmol) under reflux for 1 h. After cooling, ethyl 2-(phenylsulfonyl)acetate (428 mg, 1.87 mmol), DMF (1.5 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 761 mg, 5 mmol) were added and stirred for 6 h. Then the reaction mixture was added dropwise to ice water (20 ml) to give a yellow solid (259 mg), which was dissolved in 2-propanol. Pale yellow rhomboid-shaped crystals of (I) formed upon evaporation after 7d.