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Acta Cryst. (2009). E65, o2312    [ doi:10.1107/S1600536809034163 ]

Ethyl 3-[2-(p-toluenesulfonamido)phenyl]acrylate

M.-F. Jin and B.-Y. Zhu

Abstract top

In the title compound, C18H19NO4S, the two benzene rings form a dihedral angle of 52.2 (7)°. The crystal struture is stabilized by N-H...O hydrogen bonds, which link the molecules into dimers.

Comment top

Electron-deficient olefin, particularly α,β-unsaturated carbonyl compound, was used as a fundamental material to construct functionalized carbon frameworks (Mukherjee et al., 2007). Sulfonamido is an important group in natural compounds and many pharmaceuticals (Patchett et al., 1995). We selected N-(2-formylphenyl)(4-methylbenzene)sulfonamide and (ethoxycarbonylmethylene)triphenylphosphorane to synthesize a new compound formulated as C18H19N1O4S1 (I) with dimeric structures via hydrogen bonds.

The molecular structure of (I) is illustrated in Fig. 1. The geometry of the molecule is close to the related compound Ethyl 2-([N-(2- iodophenyl)phenylsulfonamido]methyl)-1-phenylsulfonyl-1H-indole-3- carboxylate (Senthil Kumar, et al., 2006). Bond lengths and angles (S1—O1 =1.427 (1) Å, S1—O2 = 1.431 (1) Å, O1-S1-O2 = 121.3 (1) °, O1-S1-N1 = 107.3 (9) °, O2S1N1 = 104.7 (1) °) involving the S atom of the phenylsufonyl group present in the molecule is similar to the distances (S1—O1 = 1.425 Å, S1—O2 = 1.429 Å) and angles (O1-S1-O2 = 120.4 (8) °, O1-S1-N1 = 106.9 (7) °, O2-S1-N1 = 106.7 (7) °)) that reported in the literature (Senthil Kumar, et al., 2006); the O—S—O, N—S—C and N—S—O angles deviate significantly from the ideal tetrahedral value (Table 1), which is consistent to the reported data in the literature (Senthil Kumar, et al., 2006). The phenyl rings (C2—>C7) and (C8—>C13) are planar to within 0.01 Å. The dihedral angle between the two phenyl rings is 52.3 (1) °.

The crystal struture is further stabilized by hydrogen bonding. As shown in Fig.2, a dimeric structure is formed via intermolecular hydrogen bonds N1—H2···O3i (i = 1 - x, 1 - y, -z) (Table 2).

Related literature top

For functionalized carbon framework, see: Mukherjee et al. (2007).

For sulfonamido compounds and their use in pharmaceuticals, see: Patchett et al. (1995). For a related structure, see: Senthil Kumaret al. (2006).

Experimental top

The mixture of N-(2-formylphenyl)(4-methylbenzene)sulfonamide (0.500 g, 1.82 mmol) and (ethoxycarbonylmethylene)triphenylphosphorane (0.700 g, 2.00 mmol) in dichloromethane (10 ml) was stirred at room temperature for 2 h (Scheme 2). After evaporation of the solvent, the title compound was obtained from the residue by chromatography. Single crystals suitable for X-ray analysis were obtained from ethyl acetate by slow evaporation.

Refinement top

All H atoms were fixed geometrically and treated as riding with C—H = 0.93-0.96 Å and N—H = 0.92 Å, and Uiso(H) = 1.2-1.5 Ueq(host).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); 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 CAMERON (Pearce & Watkin, 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoide are drawn at 30% probability level.
[Figure 2] Fig. 2. The dimeric structure of the title compound. Dotted lines indicate hydrogen bonds [Symmetry code: (i) = 1 - x, 1 - y, -z.]
[Figure 3] Fig. 3. The formation of the title compound.
Ethyl 3-[2-(p-toluenesulfonamido)phenyl]acrylate top
Crystal data top
C18H19NO4SZ = 2
Mr = 345.40F(000) = 364
Triclinic, P1Dx = 1.314 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.001 (4) ÅCell parameters from 8607 reflections
b = 10.245 (5) Åθ = 2.8–29.2°
c = 11.402 (5) ŵ = 0.21 mm−1
α = 81.182 (5)°T = 291 K
β = 70.895 (4)°Block, colourless
γ = 86.604 (5)°0.46 × 0.43 × 0.38 mm
V = 872.7 (8) Å3
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		3553 independent reflections
Radiation source: fine-focus sealed tube2784 reflections with I > 2σ(I)
graphiteRint = 0.020
Detector resolution: 15.9149 pixels mm-1θmax = 26.4°, θmin = 2.8°
ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		k = −12→12
Tmin = 0.91, Tmax = 0.93l = −14→14
15343 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.0903P)2]
where P = (Fo2 + 2Fc2)/3
3553 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C18H19NO4Sγ = 86.604 (5)°
Mr = 345.40V = 872.7 (8) Å3
Triclinic, P1Z = 2
a = 8.001 (4) ÅMo Kα radiation
b = 10.245 (5) ŵ = 0.21 mm−1
c = 11.402 (5) ÅT = 291 K
α = 81.182 (5)°0.46 × 0.43 × 0.38 mm
β = 70.895 (4)°
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		3553 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2784 reflections with I > 2σ(I)
Tmin = 0.91, Tmax = 0.93Rint = 0.020
15343 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.147Δρmax = 0.24 e Å−3
S = 1.18Δρmin = −0.28 e Å−3
3553 reflectionsAbsolute structure: ?
219 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.72847 (6)0.25225 (4)0.25492 (5)0.0646 (2)
O10.70944 (18)0.19430 (14)0.38058 (14)0.0831 (5)
O20.86898 (18)0.21412 (15)0.15094 (16)0.0947 (5)
O30.4015 (2)0.67440 (14)0.03433 (11)0.0782 (4)
O40.2137 (2)0.78869 (13)0.17227 (12)0.0891 (5)
N10.54807 (18)0.22083 (13)0.22784 (12)0.0526 (4)
H10.55610.24760.14540.063*
C10.7190 (4)0.8460 (2)0.2182 (3)0.1029 (8)
H1A0.80380.88330.14080.154*
H1B0.74510.87320.28720.154*
H1C0.60240.87610.21980.154*
C20.7276 (3)0.69829 (19)0.22896 (18)0.0662 (5)
C30.7857 (3)0.6372 (2)0.12236 (19)0.0740 (6)
H30.82280.68880.04400.089*
C40.7895 (3)0.5024 (2)0.12980 (18)0.0690 (5)
H40.82750.46290.05710.083*
C50.7361 (2)0.42488 (17)0.24668 (16)0.0548 (4)
C60.6821 (2)0.4838 (2)0.35380 (17)0.0640 (5)
H60.64840.43260.43240.077*
C70.6786 (3)0.6198 (2)0.34324 (19)0.0706 (5)
H70.64190.65950.41580.085*
C80.3783 (2)0.22505 (15)0.32128 (13)0.0459 (4)
C90.3306 (2)0.11643 (16)0.41448 (14)0.0533 (4)
H90.41050.04700.41630.064*
C100.1657 (2)0.11117 (18)0.50398 (15)0.0598 (5)
H100.13460.03860.56630.072*
C110.0473 (2)0.21322 (19)0.50108 (16)0.0643 (5)
H11−0.06470.20910.56090.077*
C120.0937 (2)0.32127 (18)0.41022 (16)0.0578 (4)
H120.01220.38970.40950.069*
C130.2609 (2)0.33082 (15)0.31862 (13)0.0461 (4)
C140.3083 (2)0.44882 (16)0.22402 (14)0.0494 (4)
H140.40040.43980.15050.059*
C150.2336 (3)0.56488 (18)0.23341 (15)0.0671 (5)
H150.13970.57610.30520.080*
C160.2919 (3)0.67872 (17)0.13510 (15)0.0592 (5)
C170.2604 (4)0.9087 (2)0.08528 (19)0.1009 (9)
H17A0.38550.90730.03800.121*
H17B0.19450.91600.02660.121*
C180.2205 (4)1.0191 (2)0.1528 (2)0.0906 (7)
H18A0.24211.09940.09470.136*
H18B0.29411.01580.20490.136*
H18C0.09851.01620.20420.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0528 (3)0.0488 (3)0.0846 (4)0.0071 (2)−0.0191 (2)0.0037 (2)
O10.0854 (10)0.0685 (9)0.1021 (11)−0.0082 (7)−0.0561 (9)0.0283 (8)
O20.0584 (8)0.0700 (10)0.1324 (13)0.0181 (7)−0.0011 (8)−0.0179 (9)
O30.1002 (10)0.0654 (9)0.0459 (7)0.0207 (7)−0.0027 (7)0.0068 (6)
O40.1339 (13)0.0402 (7)0.0584 (8)0.0133 (7)0.0093 (8)0.0022 (6)
N10.0575 (8)0.0454 (7)0.0484 (7)0.0050 (6)−0.0125 (6)0.0007 (6)
C10.153 (2)0.0586 (13)0.1080 (18)−0.0072 (14)−0.0580 (17)−0.0062 (13)
C20.0749 (12)0.0547 (11)0.0725 (12)−0.0066 (9)−0.0297 (10)−0.0035 (9)
C30.0894 (14)0.0598 (12)0.0637 (11)−0.0128 (10)−0.0193 (10)0.0107 (9)
C40.0772 (13)0.0585 (11)0.0595 (11)−0.0064 (9)−0.0077 (9)−0.0030 (9)
C50.0429 (9)0.0537 (10)0.0604 (10)−0.0024 (7)−0.0112 (7)0.0031 (8)
C60.0629 (11)0.0661 (12)0.0553 (10)−0.0075 (9)−0.0140 (8)0.0063 (9)
C70.0790 (13)0.0664 (13)0.0641 (11)−0.0047 (10)−0.0171 (10)−0.0138 (9)
C80.0542 (9)0.0409 (8)0.0429 (8)−0.0037 (7)−0.0170 (7)−0.0030 (6)
C90.0689 (11)0.0417 (9)0.0497 (9)−0.0031 (8)−0.0232 (8)0.0023 (7)
C100.0731 (12)0.0512 (10)0.0521 (9)−0.0173 (9)−0.0202 (9)0.0082 (7)
C110.0575 (10)0.0652 (12)0.0594 (10)−0.0140 (9)−0.0078 (8)0.0042 (9)
C120.0506 (9)0.0557 (10)0.0614 (10)−0.0013 (8)−0.0151 (8)0.0025 (8)
C130.0504 (9)0.0438 (9)0.0433 (8)−0.0033 (7)−0.0169 (7)0.0008 (6)
C140.0536 (9)0.0459 (9)0.0429 (8)0.0040 (7)−0.0121 (7)0.0013 (6)
C150.0839 (13)0.0472 (10)0.0487 (9)0.0063 (9)0.0029 (9)0.0008 (8)
C160.0737 (12)0.0467 (10)0.0475 (9)0.0056 (8)−0.0093 (8)−0.0025 (7)
C170.166 (2)0.0426 (11)0.0665 (13)−0.0021 (13)−0.0062 (14)0.0073 (9)
C180.128 (2)0.0522 (12)0.0851 (15)−0.0036 (12)−0.0264 (14)−0.0070 (11)
Geometric parameters (Å, °) top
S1—O11.4268 (15)C7—H70.9300
S1—O21.4282 (15)C8—C91.391 (2)
S1—N11.6308 (16)C8—C131.395 (2)
S1—C51.760 (2)C9—C101.377 (2)
O3—C161.201 (2)C9—H90.9300
O4—C161.315 (2)C10—C111.373 (3)
O4—C171.440 (2)C10—H100.9300
N1—C81.429 (2)C11—C121.372 (2)
N1—H10.9203C11—H110.9300
C1—C21.499 (3)C12—C131.400 (2)
C1—H1A0.9600C12—H120.9300
C1—H1B0.9600C13—C141.468 (2)
C1—H1C0.9600C14—C151.302 (2)
C2—C71.371 (3)C14—H140.9300
C2—C31.383 (3)C15—C161.468 (2)
C3—C41.371 (3)C15—H150.9300
C3—H30.9300C17—C181.427 (3)
C4—C51.390 (2)C17—H17A0.9700
C4—H40.9300C17—H17B0.9700
C5—C61.376 (3)C18—H18A0.9600
C6—C71.380 (3)C18—H18B0.9600
C6—H60.9300C18—H18C0.9600
O1—S1—O2121.53 (10)C10—C9—C8120.32 (16)
O1—S1—N1107.04 (8)C10—C9—H9119.8
O2—S1—N1104.81 (9)C8—C9—H9119.8
O1—S1—C5108.14 (9)C11—C10—C9119.93 (16)
O2—S1—C5107.81 (8)C11—C10—H10120.0
N1—S1—C5106.63 (7)C9—C10—H10120.0
C16—O4—C17117.49 (15)C12—C11—C10120.17 (17)
C8—N1—S1121.54 (11)C12—C11—H11119.9
C8—N1—H1118.1C10—C11—H11119.9
S1—N1—H1111.8C11—C12—C13121.51 (17)
C2—C1—H1A109.5C11—C12—H12119.2
C2—C1—H1B109.5C13—C12—H12119.2
H1A—C1—H1B109.5C8—C13—C12117.60 (14)
C2—C1—H1C109.5C8—C13—C14122.03 (14)
H1A—C1—H1C109.5C12—C13—C14120.38 (15)
H1B—C1—H1C109.5C15—C14—C13126.10 (15)
C7—C2—C3118.06 (19)C15—C14—H14116.9
C7—C2—C1121.61 (19)C13—C14—H14116.9
C3—C2—C1120.33 (18)C14—C15—C16122.61 (16)
C4—C3—C2121.34 (18)C14—C15—H15118.7
C4—C3—H3119.3C16—C15—H15118.7
C2—C3—H3119.3O3—C16—O4123.41 (17)
C3—C4—C5119.55 (19)O3—C16—C15124.92 (17)
C3—C4—H4120.2O4—C16—C15111.63 (15)
C5—C4—H4120.2C18—C17—O4109.33 (17)
C6—C5—C4119.91 (17)C18—C17—H17A109.8
C6—C5—S1120.91 (13)O4—C17—H17A109.8
C4—C5—S1119.11 (14)C18—C17—H17B109.8
C5—C6—C7119.18 (17)O4—C17—H17B109.8
C5—C6—H6120.4H17A—C17—H17B108.3
C7—C6—H6120.4C17—C18—H18A109.5
C2—C7—C6121.93 (18)C17—C18—H18B109.5
C2—C7—H7119.0H18A—C18—H18B109.5
C6—C7—H7119.0C17—C18—H18C109.5
C9—C8—C13120.45 (15)H18A—C18—H18C109.5
C9—C8—N1117.27 (15)H18B—C18—H18C109.5
C13—C8—N1122.25 (13)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.922.012.920 (2)172
Symmetry codes: (i) −x+1, −y+1, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.922.012.920 (2)172
Symmetry codes: (i) −x+1, −y+1, −z.
references
References top

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Patchett, A. A., Nargund, R. P. & Tata, J. R. (1995). Proc. Natl Acad. Sci. USA, 92, 7001–7005.

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