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Acta Cryst. (2009). E65, o483    [ doi:10.1107/S160053680900292X ]

Ethyl 2-[N-(2-formylphenyl)benzenesulfonamido]acetate

S. Ranjith, P. Sugumar, R. Sureshbabu, A. K. Mohanakrishnan and M. N. Ponnuswamy

Abstract top

In the molecule of the title compound, C17H17NO5S, the two aromatic rings are oriented at an angle of 30.13 (10)°. The ethyl acetate group assumes an extended conformation. Molecules are linked into C(7) chains running along the a axis by intermolecular C-H...O hydrogen bonds, and the chains are crosslinked via C-H...[pi] interactions, with the sulfonyl-bound phenyl ring acting as an acceptor.

Comment top

The title compound is a potential intermediate for the synthesis of 2-alkylbenzoic acid and exhibits insecticidal, germicidal and antimicrobial activities (Krishnaiah et al., 1995; Dupont et al., 1978). The sulfonamides inhibit the growth of bacterial organism and are also useful for treating urinary and gastrointestinal infections (Sethu Sankar et al., 2002).

Atom S1 has a distorted tetrahedral configuration. The widening of angle O2—S1—O3 [120.46 (10)°] and narrowing of angle C8—S1—N1 [105.97 (8)°] from the ideal tetrahedral value are attributed to the Thorpe-Ingold effect (Bassindale, 1984). The two phenyl rings are oriented at an angle of 30.13 (10)°. The ethylacetate moiety assumes an extended conformation as can be seen from torsion angles C14—C15—O5—C16 of 178.12 (15)° and C15—O5—C16—C17 of 173.12 (19)°.

The molecules are linked into C(7) chains running along the a axis by C—H···O hydrogen bonding (Table 1). In addition C—H···π interactions (Table 1) with C8–C13 ring (centroid Cg1) as an acceptor is observed.

Related literature top

For the activities of sulfonamides, see: Krishnaiah et al. (1995); Dupont et al. (1978); Sethu Sankar et al. (2002). For related literature, see: Bassindale (1984).

Experimental top

2-(Benzenesulfonylamino)benzaldehyde (2 mmol) was added with ethyl bromoacetate (2.2 mmol) in the presence of potassium carbonate (4.7 mmol) and dimethyl acetamide (15 ml). The mixture was stirred at room temperature for 6 h. The reaction mass was poured into crushed ice (50 g) containing 4 to 5 drops of concentrated HCl and extracted with ethyl acetate. The product was obtained by column chromatography (hexane-ethyl acetate 9:1). The removal of the solvent followed by column chromatography of the residue (ethyl acetate) afforded white crystalline solid (yield 25%, m.p. 381-383 K). Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution of the title compound at room temperature.

Refinement top

H atoms were positioned geometrically (C-H = 0.93-0.97 Å) and were treated as riding on their parent C atoms with Uiso(H) = 1.2-1.5Ueq(C). The Uij components of atoms C1, C2 and C6 in the direction of the bond between them were restrained to be equal within an effective standard deviation of 0.001.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004; 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 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Molecular packing in the title compound, viewed down the b axis. Dashed lines represent hydrogen bonds.
Ethyl 2-[N-(2-formylphenyl)benzenesulfonamido]acetate top
Crystal data top
C17H17NO5SF(000) = 728
Mr = 347.38Dx = 1.347 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5831 reflections
a = 11.3512 (6) Åθ = 2.4–31.9°
b = 11.7820 (6) ŵ = 0.22 mm−1
c = 12.8045 (6) ÅT = 293 K
V = 1712.47 (15) Å3Block, white
Z = 40.25 × 0.22 × 0.19 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5831 independent reflections
Radiation source: fine-focus sealed tube3738 reflections with I > 2σ(I)
graphiteRint = 0.024
ω and φ scansθmax = 31.9°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→16
Tmin = 0.948, Tmax = 0.960k = −17→14
13978 measured reflectionsl = −19→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0543P)2 + 0.0353P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5831 reflectionsΔρmax = 0.29 e Å−3
218 parametersΔρmin = −0.25 e Å−3
2 restraintsAbsolute structure: Flack (1983), 2533 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (6)
Crystal data top
C17H17NO5SV = 1712.47 (15) Å3
Mr = 347.38Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.3512 (6) ŵ = 0.22 mm−1
b = 11.7820 (6) ÅT = 293 K
c = 12.8045 (6) Å0.25 × 0.22 × 0.19 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5831 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3738 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.960Rint = 0.024
13978 measured reflectionsθmax = 31.9°
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.29 e Å−3
S = 1.02Δρmin = −0.25 e Å−3
5831 reflectionsAbsolute structure: Flack (1983), 2533 Friedel pairs
218 parametersFlack parameter: 0.04 (6)
2 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6483 (2)0.49883 (17)0.57621 (17)0.0725 (5)
H10.66430.55350.62660.087*
C20.7343 (2)0.46784 (15)0.50573 (16)0.0599 (4)
H20.80760.50300.50790.072*
C30.71222 (15)0.38413 (13)0.43117 (13)0.0455 (4)
C40.60095 (14)0.33360 (13)0.42953 (13)0.0439 (4)
C50.51443 (18)0.36705 (17)0.49915 (16)0.0601 (5)
H50.44010.33410.49650.072*
C60.5388 (2)0.44896 (19)0.57199 (17)0.0749 (5)
H60.48070.47110.61900.090*
C70.80521 (16)0.35124 (16)0.35744 (16)0.0541 (4)
H70.79220.28850.31490.065*
C80.38129 (14)0.27847 (14)0.23805 (13)0.0441 (3)
C90.31891 (18)0.18498 (16)0.20531 (16)0.0567 (5)
H90.35820.12110.18070.068*
C100.1974 (2)0.18686 (19)0.20932 (19)0.0706 (6)
H100.15440.12430.18670.085*
C110.14047 (18)0.2805 (2)0.24649 (18)0.0712 (6)
H110.05860.28110.24990.085*
C120.20264 (19)0.37386 (19)0.27891 (17)0.0684 (6)
H120.16270.43710.30410.082*
C130.32368 (18)0.37453 (15)0.27450 (15)0.0554 (4)
H130.36610.43810.29550.066*
C140.54399 (17)0.13373 (14)0.39808 (16)0.0540 (4)
H14A0.50150.09110.34530.065*
H14B0.49190.14440.45730.065*
C150.65056 (17)0.06720 (14)0.43210 (14)0.0493 (4)
C160.7056 (2)−0.10263 (15)0.51699 (17)0.0665 (6)
H16A0.7630−0.06240.55920.080*
H16B0.7459−0.13670.45800.080*
C170.6456 (3)−0.1912 (2)0.5801 (3)0.1116 (11)
H17A0.6075−0.15650.63890.167*
H17B0.7026−0.24530.60440.167*
H17C0.5879−0.22920.53780.167*
N10.57707 (12)0.24388 (11)0.35598 (11)0.0472 (3)
O10.89698 (13)0.40067 (14)0.34903 (16)0.0853 (5)
O20.58147 (12)0.38549 (11)0.21580 (11)0.0643 (4)
O30.57026 (13)0.18131 (14)0.17302 (12)0.0758 (4)
O40.75012 (13)0.09354 (12)0.41701 (15)0.0768 (5)
O50.61509 (11)−0.02585 (10)0.48124 (11)0.0592 (3)
S10.53632 (4)0.27483 (4)0.23629 (3)0.04953 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.1104 (14)0.0522 (10)0.0549 (11)0.0040 (10)−0.0043 (10)−0.0089 (9)
C20.0728 (13)0.0477 (9)0.0593 (10)−0.0020 (9)−0.0145 (8)0.0032 (8)
C30.0469 (9)0.0410 (8)0.0484 (8)0.0041 (7)−0.0058 (7)0.0073 (7)
C40.0445 (9)0.0421 (8)0.0451 (8)0.0043 (7)−0.0039 (7)0.0069 (7)
C50.0544 (11)0.0629 (11)0.0629 (11)0.0072 (9)0.0080 (9)0.0063 (9)
C60.0906 (13)0.0731 (12)0.0611 (11)0.0163 (12)0.0180 (13)−0.0021 (10)
C70.0456 (10)0.0544 (10)0.0624 (11)0.0023 (9)−0.0015 (8)0.0070 (8)
C80.0436 (8)0.0493 (8)0.0395 (7)0.0012 (7)−0.0038 (6)−0.0011 (8)
C90.0585 (12)0.0463 (9)0.0653 (12)0.0026 (9)−0.0056 (9)−0.0044 (8)
C100.0562 (12)0.0676 (12)0.0879 (15)−0.0114 (11)−0.0087 (11)0.0002 (11)
C110.0472 (10)0.0903 (16)0.0763 (14)0.0025 (11)0.0026 (10)−0.0014 (13)
C120.0615 (12)0.0784 (14)0.0653 (12)0.0238 (11)−0.0038 (10)−0.0146 (11)
C130.0579 (11)0.0552 (10)0.0532 (9)0.0078 (8)−0.0074 (8)−0.0093 (8)
C140.0459 (10)0.0443 (8)0.0719 (10)−0.0015 (8)−0.0038 (9)0.0079 (8)
C150.0518 (10)0.0414 (8)0.0546 (9)−0.0014 (8)−0.0071 (8)−0.0024 (8)
C160.0828 (15)0.0493 (9)0.0674 (12)0.0114 (10)−0.0237 (11)0.0029 (9)
C170.133 (3)0.0727 (16)0.129 (3)−0.0176 (16)−0.048 (2)0.0442 (17)
N10.0434 (7)0.0416 (7)0.0567 (8)−0.0004 (6)−0.0075 (6)0.0048 (6)
O10.0493 (8)0.0925 (11)0.1142 (13)−0.0147 (8)0.0139 (8)−0.0077 (10)
O20.0613 (8)0.0729 (9)0.0587 (7)−0.0149 (7)−0.0028 (6)0.0174 (7)
O30.0589 (9)0.0942 (11)0.0743 (9)0.0085 (8)0.0091 (7)−0.0305 (8)
O40.0472 (8)0.0625 (8)0.1207 (13)0.0017 (7)−0.0119 (8)0.0208 (9)
O50.0664 (8)0.0460 (6)0.0652 (8)0.0016 (6)−0.0078 (6)0.0095 (6)
S10.0434 (2)0.0569 (2)0.0483 (2)0.0004 (2)0.00160 (19)−0.00257 (19)
Geometric parameters (Å, °) top
C1—C61.376 (3)C11—C121.371 (3)
C1—C21.378 (3)C11—H110.93
C1—H10.93C12—C131.375 (3)
C2—C31.395 (3)C12—H120.93
C2—H20.93C13—H130.93
C3—C41.396 (2)C14—N11.455 (2)
C3—C71.468 (2)C14—C151.506 (3)
C4—C51.384 (2)C14—H14A0.97
C4—N11.442 (2)C14—H14B0.97
C5—C61.370 (3)C15—O41.188 (2)
C5—H50.93C15—O51.327 (2)
C6—H60.93C16—O51.443 (2)
C7—O11.198 (2)C16—C171.486 (3)
C7—H70.93C16—H16A0.97
C8—C91.375 (2)C16—H16B0.97
C8—C131.388 (2)C17—H17A0.96
C8—S11.7605 (16)C17—H17B0.96
C9—C101.380 (3)C17—H17C0.96
C9—H90.93N1—S11.6419 (14)
C10—C111.365 (3)O2—S11.4253 (13)
C10—H100.93O3—S11.4209 (15)
C6—C1—C2120.05 (19)C13—C12—H12119.8
C6—C1—H1120.0C12—C13—C8118.67 (18)
C2—C1—H1120.0C12—C13—H13120.7
C1—C2—C3120.5 (2)C8—C13—H13120.7
C1—C2—H2119.7N1—C14—C15111.36 (15)
C3—C2—H2119.7N1—C14—H14A109.4
C2—C3—C4118.28 (17)C15—C14—H14A109.4
C2—C3—C7119.84 (17)N1—C14—H14B109.4
C4—C3—C7121.88 (16)C15—C14—H14B109.4
C5—C4—C3120.73 (16)H14A—C14—H14B108.0
C5—C4—N1119.76 (16)O4—C15—O5125.58 (17)
C3—C4—N1119.50 (15)O4—C15—C14125.54 (16)
C6—C5—C4119.74 (19)O5—C15—C14108.88 (15)
C6—C5—H5120.1O5—C16—C17106.6 (2)
C4—C5—H5120.1O5—C16—H16A110.4
C5—C6—C1120.6 (2)C17—C16—H16A110.4
C5—C6—H6119.7O5—C16—H16B110.4
C1—C6—H6119.7C17—C16—H16B110.4
O1—C7—C3123.7 (2)H16A—C16—H16B108.6
O1—C7—H7118.2C16—C17—H17A109.5
C3—C7—H7118.2C16—C17—H17B109.5
C9—C8—C13120.88 (16)H17A—C17—H17B109.5
C9—C8—S1119.43 (13)C16—C17—H17C109.5
C13—C8—S1119.68 (14)H17A—C17—H17C109.5
C8—C9—C10119.37 (18)H17B—C17—H17C109.5
C8—C9—H9120.3C4—N1—C14117.44 (14)
C10—C9—H9120.3C4—N1—S1119.99 (10)
C11—C10—C9119.9 (2)C14—N1—S1118.12 (12)
C11—C10—H10120.0C15—O5—C16116.89 (15)
C9—C10—H10120.0O3—S1—O2120.46 (10)
C10—C11—C12120.7 (2)O3—S1—N1106.47 (9)
C10—C11—H11119.7O2—S1—N1105.88 (8)
C12—C11—H11119.7O3—S1—C8107.29 (9)
C11—C12—C13120.43 (19)O2—S1—C8109.85 (9)
C11—C12—H12119.8N1—S1—C8105.97 (8)
C6—C1—C2—C3−1.4 (3)N1—C14—C15—O5172.45 (14)
C1—C2—C3—C40.5 (3)C5—C4—N1—C14−59.0 (2)
C1—C2—C3—C7−179.31 (18)C3—C4—N1—C14119.59 (16)
C2—C3—C4—C50.9 (2)C5—C4—N1—S196.88 (17)
C7—C3—C4—C5−179.28 (16)C3—C4—N1—S1−84.51 (17)
C2—C3—C4—N1−177.66 (14)C15—C14—N1—C4−81.22 (19)
C7—C3—C4—N12.1 (2)C15—C14—N1—S1122.42 (14)
C3—C4—C5—C6−1.4 (3)O4—C15—O5—C16−1.6 (3)
N1—C4—C5—C6177.22 (17)C14—C15—O5—C16178.12 (15)
C4—C5—C6—C10.4 (3)C17—C16—O5—C15173.12 (19)
C2—C1—C6—C51.0 (3)C4—N1—S1—O3154.32 (14)
C2—C3—C7—O1−8.5 (3)C14—N1—S1—O3−49.95 (15)
C4—C3—C7—O1171.70 (19)C4—N1—S1—O224.99 (16)
C13—C8—C9—C10−0.3 (3)C14—N1—S1—O2−179.28 (13)
S1—C8—C9—C10178.31 (17)C4—N1—S1—C8−91.66 (14)
C8—C9—C10—C11−0.6 (3)C14—N1—S1—C864.07 (15)
C9—C10—C11—C120.8 (3)C9—C8—S1—O315.45 (17)
C10—C11—C12—C130.0 (3)C13—C8—S1—O3−165.94 (15)
C11—C12—C13—C8−0.9 (3)C9—C8—S1—O2148.05 (15)
C9—C8—C13—C121.0 (3)C13—C8—S1—O2−33.34 (17)
S1—C8—C13—C12−177.55 (16)C9—C8—S1—N1−98.00 (15)
N1—C14—C15—O4−7.8 (3)C13—C8—S1—N180.61 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.932.573.220 (2)127
C16—H16B···Cg1ii0.972.753.615 (2)150
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x+3/2, −y−1/2, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.932.573.220 (2)127
C16—H16B···Cg1ii0.972.753.615 (2)150
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x+3/2, −y−1/2, −z.
Acknowledgements top

SR and MNP thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

references
References top

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.