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Acta Cryst. (2009). E65, o530    [ doi:10.1107/S1600536809004413 ]

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

P. R. Seshadri, B. Balakrishnan, K. Ilangovan, R. Sureshbabu and A. K. Mohanakrishnan

Abstract top

In the title compound, C17H17NO5S, the N atom is sp3-hybridized and the S atom has a distorted tetrahedral configuration. The dihedral angle between the two aromatic rings is 30.0 (1)°, and that between the ethyl acetate group and the formylphenyl ring is 77.4 (1)°. The molecules are linked into chains along [100] by C-H...O hydrogen bonds and the chains are linked via C-H...[pi] interactions.

Comment top

Sulfonamide derivates are well known drugs and are used to control diseases caused by bacterial infections. The antibacterial action of this group of drugs is exerted by the complete inhibition of dihydropteroate synthase enzyme towards the p-amino benzonate (Brown, 1971). Benzene sulfonamide derivatives are known to exhibit anticancer and HIV activities (Pomarnacka & Kozlarska-Kedra, 2003) and antibacterial activities (Nieto et al., 2005). In view of this medicinal importance, the crystal structure determination of the title compound (Fig.1) was carried out and the results are presented here.

The angles around atom S1 deviate significantly from the regular tetrahedral value, with the largest deviation of 120.6 (1)° for O1—S1—O2 angle. This may be due to non-bonding interactions between S═O bonds (Cotton & Stokley, 1970). The sulfonyl oxygen O1 is syn-clinal and O2 is syn-periplanar to the phenyl ring. The dihedral angle between the best planes through the ethylacetate group (O3/O4/C14/C15/C16) and formyl phenyl ring (C7-C12) is 77.4 (1)°. The aldyhyde group is slightly twisted from the plane of the ring to which it is attached as evidenced by the torsion angle C11—C12—C13—O5 of -8.5 (3)°. The relative orientations of C/N/S and O/S/O planes is determined by the hybridization nature of atom N1. The angles between planes C14/N1/S1 and O1/S1/O2 and between C7/N1/S1 and O1/S1/O2 planes are 59° and 56°, respectively. These values are close to 58° reported for sp3 N atoms [87° for sp2 N atoms] (Cameron et al., 1975). The geometrical parameters agree well with those reported for related sulfonamide structures (Usha et al., 2005; Zhu et al., 2008).

In addition to van der Waals interactions, the crystal structure is stabilized by C—H···O and C—H···π interactions (Table 1).

Related literature top

For the biological properties of sulfonamide derivatives, see: Brown (1971); Nieto et al. (2005); Pomarnacka & Kozlarska-Kedra (2003). For related structures, see: Cameron et al. (1975); Cotton & Stokley (1970); Usha et al. (2005); Zhu et al. (2008).

Experimental top

N-(2-Formylphenyl)benzene sulfonamide (1.7 g, 6.5 mmol) was dissolved in dimethyl acetamide (25 ml). To this potassium carbonate (2.25 g, 16.2 mmol) and ethyl bromoacetate (0.86 ml, 7.8 mmol) were added. The reaction mixture was stirred at room temperature for 4 h. It was then poured over curshed ice (100 g) cotaining 5 ml of concentrated HCl. The precipitated solid was filtered off and the title compound was recrystallized from methanol. Yield = 1 g (45%) and m.p = 381 K.

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C-H = 0.93-0.97 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms.

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) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.
Ethyl 2-[N-(2-Formylphenyl)benzenesulfonamido]acetate top
Crystal data top
C17H17NO5SF(000) = 728
Mr = 347.38Dx = 1.352 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4197 reflections
a = 11.3442 (5) Åθ = 2.4–28.2°
b = 11.7731 (6) ŵ = 0.22 mm−1
c = 12.7809 (6) ÅT = 293 K
V = 1706.97 (14) Å3Block, colourless
Z = 40.25 × 0.20 × 0.20 mm
Data collection top
Bruker Kappa APEXII area-detector
diffractometer		4104 independent reflections
Radiation source: fine-focus sealed tube3294 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 28.2°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		h = −15→10
Tmin = 0.948, Tmax = 0.958k = −13→15
10886 measured reflectionsl = −17→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)] = 0.036H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.2327P]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.001
4104 reflectionsΔρmax = 0.31 e Å−3
218 parametersΔρmin = −0.23 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1714 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.05 (7)
Crystal data top
C17H17NO5SV = 1706.97 (14) Å3
Mr = 347.38Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.3442 (5) ŵ = 0.22 mm−1
b = 11.7731 (6) ÅT = 293 K
c = 12.7809 (6) Å0.25 × 0.20 × 0.20 mm
Data collection top
Bruker Kappa APEXII area-detector
diffractometer		4104 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		3294 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.958Rint = 0.022
10886 measured reflectionsθmax = 28.2°
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.092Δρmax = 0.31 e Å−3
S = 0.95Δρmin = −0.23 e Å−3
4104 reflectionsAbsolute structure: Flack (1983), 1714 Friedel pairs
218 parametersFlack parameter: −0.05 (7)
0 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
S10.53613 (4)0.77486 (4)0.23609 (3)0.04875 (13)
N10.57693 (13)0.74419 (13)0.35602 (12)0.0458 (4)
O10.58109 (13)0.88549 (13)0.21568 (11)0.0627 (4)
O20.56980 (14)0.68125 (16)0.17264 (13)0.0734 (5)
O30.75001 (14)0.59352 (14)0.41673 (16)0.0749 (5)
O40.61531 (12)0.47431 (12)0.48118 (11)0.0576 (4)
O50.89664 (14)0.90059 (16)0.34906 (17)0.0833 (6)
C10.38089 (15)0.77875 (16)0.23788 (14)0.0433 (4)
C20.3190 (2)0.68510 (18)0.20483 (17)0.0559 (5)
H20.35850.62150.17980.067*
C30.1975 (2)0.6866 (2)0.2093 (2)0.0693 (6)
H30.15460.62370.18700.083*
C40.1400 (2)0.7802 (2)0.24649 (19)0.0705 (6)
H40.05810.78060.24960.085*
C50.2021 (2)0.8738 (2)0.27923 (18)0.0660 (6)
H5A0.16220.93710.30460.079*
C60.32367 (19)0.87418 (18)0.27450 (16)0.0547 (5)
H60.36630.93760.29560.066*
C70.60070 (16)0.83376 (15)0.42938 (14)0.0430 (4)
C80.51433 (19)0.86705 (19)0.49933 (16)0.0585 (5)
H80.44000.83380.49670.070*
C90.5382 (3)0.9487 (2)0.57219 (17)0.0717 (6)
H90.47990.97080.61920.086*
C100.6472 (3)0.9983 (2)0.57653 (17)0.0713 (7)
H100.66301.05290.62730.086*
C110.7342 (2)0.96779 (17)0.50592 (16)0.0585 (5)
H110.80751.00300.50820.070*
C120.71158 (17)0.88403 (15)0.43139 (14)0.0444 (4)
C130.80492 (18)0.85128 (18)0.35747 (16)0.0525 (5)
H130.79190.78860.31480.063*
C140.54423 (19)0.63341 (16)0.39786 (16)0.0529 (4)
H14A0.50220.59080.34470.064*
H14B0.49170.64370.45700.064*
C150.65033 (19)0.56723 (17)0.43213 (15)0.0485 (4)
C160.7055 (2)0.39708 (18)0.51686 (18)0.0642 (6)
H16A0.76310.43720.55910.077*
H16B0.74570.36300.45770.077*
C170.6461 (3)0.3085 (2)0.5799 (3)0.1089 (12)
H17A0.61110.34260.64060.163*
H17B0.70270.25250.60120.163*
H17C0.58580.27290.53860.163*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0432 (2)0.0579 (3)0.0451 (2)0.0008 (2)0.0015 (2)−0.0029 (2)
N10.0426 (8)0.0414 (8)0.0535 (8)0.0000 (7)−0.0064 (6)0.0046 (7)
O10.0607 (9)0.0714 (10)0.0559 (8)−0.0149 (8)−0.0027 (7)0.0166 (7)
O20.0594 (10)0.0918 (12)0.0692 (9)0.0096 (9)0.0088 (7)−0.0290 (9)
O30.0449 (9)0.0622 (10)0.1175 (14)0.0016 (8)−0.0120 (9)0.0194 (9)
O40.0636 (9)0.0468 (8)0.0622 (8)0.0010 (7)−0.0076 (7)0.0095 (7)
O50.0478 (9)0.0929 (13)0.1093 (14)−0.0136 (9)0.0124 (9)−0.0077 (11)
C10.0411 (9)0.0509 (10)0.0380 (8)0.0016 (8)−0.0043 (7)−0.0017 (9)
C20.0555 (13)0.0491 (11)0.0630 (12)0.0033 (10)−0.0050 (9)−0.0037 (9)
C30.0548 (13)0.0680 (14)0.0852 (16)−0.0116 (12)−0.0057 (12)−0.0013 (12)
C40.0466 (11)0.0937 (18)0.0712 (14)0.0004 (13)0.0025 (10)0.0003 (14)
C50.0592 (13)0.0776 (15)0.0612 (13)0.0218 (13)−0.0023 (11)−0.0129 (12)
C60.0576 (12)0.0564 (12)0.0502 (10)0.0069 (10)−0.0082 (9)−0.0095 (9)
C70.0454 (10)0.0408 (9)0.0429 (9)0.0049 (8)−0.0035 (8)0.0058 (8)
C80.0522 (12)0.0656 (13)0.0576 (11)0.0071 (10)0.0076 (9)0.0062 (10)
C90.0859 (17)0.0712 (14)0.0579 (12)0.0135 (15)0.0170 (14)−0.0028 (11)
C100.111 (2)0.0521 (12)0.0508 (12)0.0063 (13)−0.0067 (13)−0.0087 (10)
C110.0719 (15)0.0488 (11)0.0547 (12)−0.0025 (11)−0.0150 (10)0.0027 (9)
C120.0463 (10)0.0420 (9)0.0449 (9)0.0045 (8)−0.0050 (8)0.0067 (8)
C130.0432 (11)0.0538 (11)0.0605 (12)0.0035 (10)−0.0014 (9)0.0079 (9)
C140.0452 (11)0.0452 (10)0.0684 (11)−0.0022 (10)−0.0031 (10)0.0073 (9)
C150.0523 (12)0.0427 (10)0.0505 (10)−0.0004 (9)−0.0091 (9)−0.0037 (8)
C160.0804 (16)0.0486 (11)0.0635 (13)0.0096 (11)−0.0243 (11)0.0018 (10)
C170.132 (3)0.0725 (18)0.122 (3)−0.0193 (18)−0.047 (2)0.0430 (18)
Geometric parameters (Å, °) top
S1—O11.4229 (15)C7—C81.383 (3)
S1—O21.4206 (16)C7—C121.390 (3)
S1—N11.6414 (15)C8—C91.365 (3)
S1—C11.7618 (18)C8—H80.93
N1—C71.437 (2)C9—C101.370 (4)
N1—C141.458 (2)C9—H90.93
O3—C151.189 (2)C10—C111.385 (3)
O4—C151.322 (2)C10—H100.93
O4—C161.443 (2)C11—C121.395 (3)
O5—C131.196 (3)C11—H110.93
C1—C61.379 (3)C12—C131.471 (3)
C1—C21.374 (3)C13—H130.93
C2—C31.380 (3)C14—C151.499 (3)
C2—H20.93C14—H14A0.97
C3—C41.367 (3)C14—H14B0.97
C3—H30.93C16—C171.480 (4)
C4—C51.373 (3)C16—H16A0.97
C4—H40.93C16—H16B0.97
C5—C61.381 (3)C17—H17A0.96
C5—H5A0.93C17—H17B0.96
C6—H60.93C17—H17C0.96
O1—S1—O2120.6 (1)C8—C9—H9119.8
O1—S1—N1105.7 (1)C10—C9—H9119.8
O2—S1—N1106.7 (1)C9—C10—C11120.4 (2)
O1—S1—C1109.7 (1)C9—C10—H10119.8
O2—S1—C1107.2 (1)C11—C10—H10119.8
N1—S1—C1106.0 (1)C10—C11—C12119.8 (2)
C7—N1—C14117.7 (2)C10—C11—H11120.1
C7—N1—S1120.1 (1)C12—C11—H11120.1
C14—N1—S1117.9 (1)C7—C12—C11118.69 (19)
C15—O4—C16117.27 (16)C7—C12—C13121.86 (18)
C6—C1—C2121.17 (18)C11—C12—C13119.45 (19)
C6—C1—S1119.73 (15)O5—C13—C12123.8 (2)
C2—C1—S1119.08 (15)O5—C13—H13118.1
C3—C2—C1119.2 (2)C12—C13—H13118.1
C3—C2—H2120.4N1—C14—C15111.6 (2)
C1—C2—H2120.4N1—C14—H14A109.3
C2—C3—C4120.1 (2)C15—C14—H14A109.3
C2—C3—H3120.0N1—C14—H14B109.3
C4—C3—H3120.0C15—C14—H14B109.3
C5—C4—C3120.6 (2)H14A—C14—H14B108.0
C5—C4—H4119.7O3—C15—O4125.4 (2)
C3—C4—H4119.7O3—C15—C14125.5 (2)
C4—C5—C6120.1 (2)O4—C15—C14109.11 (17)
C4—C5—H5A120.0O4—C16—C17107.0 (2)
C6—C5—H5A120.0O4—C16—H16A110.3
C1—C6—C5118.9 (2)C17—C16—H16A110.3
C1—C6—H6120.6O4—C16—H16B110.3
C5—C6—H6120.6C17—C16—H16B110.3
C8—C7—C12120.55 (19)H16A—C16—H16B108.6
C8—C7—N1119.79 (18)C16—C17—H17A109.5
C12—C7—N1119.63 (17)C16—C17—H17B109.5
C9—C8—C7120.0 (2)H17A—C17—H17B109.5
C9—C8—H8120.0C16—C17—H17C109.5
C7—C8—H8120.0H17A—C17—H17C109.5
C8—C9—C10120.5 (2)H17B—C17—H17C109.5
O1—S1—N1—C724.90 (17)C14—N1—C7—C12119.11 (18)
O2—S1—N1—C7154.43 (15)S1—N1—C7—C12−84.75 (19)
C1—S1—N1—C7−91.53 (15)C12—C7—C8—C9−1.0 (3)
O1—S1—N1—C14−179.00 (14)N1—C7—C8—C9177.16 (19)
O2—S1—N1—C14−49.47 (17)C7—C8—C9—C100.1 (3)
C1—S1—N1—C1464.58 (16)C8—C9—C10—C111.1 (4)
O1—S1—C1—C6−33.51 (18)C9—C10—C11—C12−1.5 (3)
O2—S1—C1—C6−166.12 (17)C8—C7—C12—C110.6 (3)
N1—S1—C1—C680.23 (17)N1—C7—C12—C11−177.55 (16)
O1—S1—C1—C2148.00 (16)C8—C7—C12—C13−179.43 (17)
O2—S1—C1—C215.4 (2)N1—C7—C12—C132.4 (3)
N1—S1—C1—C2−98.26 (16)C10—C11—C12—C70.6 (3)
C6—C1—C2—C3−0.5 (3)C10—C11—C12—C13−179.32 (19)
S1—C1—C2—C3177.94 (18)C7—C12—C13—O5171.5 (2)
C1—C2—C3—C4−0.2 (3)C11—C12—C13—O5−8.5 (3)
C2—C3—C4—C50.3 (4)C7—N1—C14—C15−80.8 (2)
C3—C4—C5—C60.2 (4)S1—N1—C14—C15122.49 (16)
C2—C1—C6—C51.1 (3)C16—O4—C15—O3−1.5 (3)
S1—C1—C6—C5−177.41 (17)C16—O4—C15—C14177.78 (17)
C4—C5—C6—C1−0.9 (3)N1—C14—C15—O3−8.5 (3)
C14—N1—C7—C8−59.1 (2)N1—C14—C15—O4172.19 (15)
S1—N1—C7—C897.09 (19)C15—O4—C16—C17173.1 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O3i0.932.573.218 (3)127
C16—H16B···Cg1ii0.972.733.605 (3)150
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O3i0.932.573.218 (3)127
C16—H16B···Cg1ii0.972.733.605 (3)150
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y−1/2, −z+1/2.
Acknowledgements top

BB and RS thank Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

references
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