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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o549.
Published online 2009 February 18. doi:  10.1107/S1600536809005248
PMCID: PMC2968601

2-(2-Iodo­benzenesulfonamido)acetic acid

Abstract

The title compound, C8H8INO4S, is a halogenated sulfon­amide, a medicinally important class of organic compounds. In the crystal structure, inter­molecular O—H(...)O hydrogen bonds involving the carboxylic acid groups form characteristic centrosymmetric dimers. These dimers are further linked through centrosymmetric dimeric N—H(...)O inter­actions involving the amido H atom and a sulfonyl O atom. This leads to the formation of a ribbon-like polymer structure propagating in the b direction.

Related literature

For background on sulfonamides, or sulfa drugs, see: Pandya et al. (2003 [triangle]). For the structure of the non-halogenated analogue, see: Arshad et al. (2008b [triangle]). For the synthesis of the title compound, see: Deng & Mani (2006 [triangle]). For details of related structures: see Arshad et al. (2008a [triangle],c [triangle]). For background on related thia­zine heterocycles, see: Arshad et al. (2008d [triangle]). For standard bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o549-scheme1.jpg

Experimental

Crystal data

  • C8H8INO4S
  • M r = 341.11
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o549-efi1.jpg
  • a = 5.5877 (2) Å
  • b = 8.0145 (2) Å
  • c = 12.3584 (4) Å
  • α = 80.923 (2)°
  • β = 83.398 (2)°
  • γ = 88.038 (2)°
  • V = 542.81 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.14 mm−1
  • T = 296 K
  • 0.22 × 0.10 × 0.06 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.691, T max = 0.834
  • 11492 measured reflections
  • 2691 independent reflections
  • 2297 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.086
  • S = 1.02
  • 2691 reflections
  • 137 parameters
  • H-atom parameters constrained
  • Δρmax = 1.43 e Å−3
  • Δρmin = −1.09 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005248/su2093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005248/su2093Isup2.hkl

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

Acknowledgments

MNA acknowledges the Higher Education Commission, Pakistan, for providing a PhD Scholarship under PIN 042-120607-PS2-183.

supplementary crystallographic information

Comment

Sulfonamides, commonly known as sulfa drugs, belong to a class of organic compounds which have widespread applications in Medicinal Chemistry for curing bacterial infections (Pandya et al., 2003). As a continuation of our studies on the synthesis of thiazine related compounds (Arshad et al., 2008a,b,c,d) we present here the structure of the title compound.

The molecular structure of the title compound is illustrated in Fig. 1. We have previously reported on the crystal structures of the non-halogenated analogue of the title compound, 2-(phenylsulfonamido)acetic acid, (Arshad et al., 2008b), and the K+ and Na+ salts of 2-iodobenzenesulfonates (Arshad et al., 2008a,c). The bond lengths and angles in the title compound are similar to those reported there and are within normal ranges (Allen et al., 1987).

In the crystal structure intermolecular O—H···O hydrogen bonds involving the carboxylic acid groups form characteristic centrosymmetric dimers. These dimers are further linked through centrosymmetric intermolecular N—H···O interactions involving the amido H atoms and a sulfonyl O atom (Fig. 2). This leads to the formation of a ribbon-like polymer structure propagating along the b axis. This arrangement is very similar to that observed in the non-halogenated analogue mentioned above.

Experimental

The title compound was synthesized following the literature method (Deng & Mani, 2006). Glycine methyl ester hydrochloride (207 mg, 1.653 mmol) was dissolved in distilled water (5 ml). The pH of the solution was maintained at 8–9 using 1M, Na2CO3 solution. 2-Iodo benzene sulfonyl chloride (500 mg, 1.653 mmol) was then added to the solution, which was stirred at room temperature until all the 2-iodo benzene sulfonyl chloride had been consumed. During the reaction the pH was again strictly maintained at 8–9 using 1M, Na2CO3. On completion of the reaction the pH was adjusted 1–2, using 1N HCl under vigorous stirring. The precipitate obtained was filtered off, washed with distilled water and dried. Crystals of the title compound were obtained by recrystallisation from methanol.

Refinement

The O, N and C-bound H atoms were included in calculated positions and treated as riding: O—H = 0.82 Å, N—H = 0.86 Å, C—H = 0.93–0.97 Å, with Uiso(H) = 1.5Ueq(parent O atom) and = 1.2Ueq(parent C and N atom).

Figures

Fig. 1.
Molecular structure of the title compound showing the atom labelling scheme. The thermal ellipsoids are drawn at the 50% probability level.
Fig. 2.
Crystal packing of the title compound, viewed along the axis, showing the intermolecular hydrogen bonds as dashed lines.

Crystal data

C8H8INO4SZ = 2
Mr = 341.11F(000) = 328
Triclinic, P1Dx = 2.087 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.5877 (2) ÅCell parameters from 6313 reflections
b = 8.0145 (2) Åθ = 2.6–28.3°
c = 12.3584 (4) ŵ = 3.14 mm1
α = 80.923 (2)°T = 296 K
β = 83.398 (2)°Needle-like, light brown
γ = 88.038 (2)°0.22 × 0.10 × 0.06 mm
V = 542.81 (3) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer2691 independent reflections
Radiation source: fine-focus sealed tube2297 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −7→7
Tmin = 0.691, Tmax = 0.834k = −10→10
11492 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0454P)2 + 0.6546P] where P = (Fo2 + 2Fc2)/3
2691 reflections(Δ/σ)max = 0.001
137 parametersΔρmax = 1.43 e Å3
0 restraintsΔρmin = −1.09 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/Ueq
I10.10590 (5)0.34414 (3)0.90179 (2)0.0537 (1)
S10.59293 (13)0.42594 (9)0.68657 (7)0.0327 (2)
O10.5522 (4)0.7909 (3)0.5250 (2)0.0405 (7)
O20.2240 (4)0.9320 (3)0.5837 (3)0.0506 (8)
O30.6165 (5)0.5362 (3)0.7649 (2)0.0447 (8)
O40.7874 (4)0.4121 (3)0.6022 (2)0.0448 (8)
N10.3478 (5)0.4818 (3)0.6322 (2)0.0348 (8)
C10.5418 (5)0.2165 (4)0.7568 (3)0.0319 (8)
C20.3582 (6)0.1730 (4)0.8409 (3)0.0376 (9)
C30.3352 (8)0.0057 (4)0.8907 (3)0.0496 (11)
C40.4944 (8)−0.1169 (4)0.8574 (3)0.0520 (13)
C50.6787 (8)−0.0735 (4)0.7758 (4)0.0514 (11)
C60.7032 (7)0.0926 (4)0.7254 (3)0.0434 (10)
C70.2290 (6)0.6417 (4)0.6433 (3)0.0371 (9)
C80.3550 (6)0.7946 (4)0.5770 (3)0.0346 (9)
H1N0.286400.414500.595500.0420*
H2O0.298001.013800.549300.0760*
H30.21160−0.024100.946900.0600*
H40.47630−0.228900.890500.0630*
H50.78740−0.155800.754300.0620*
H60.828700.121700.670000.0520*
H7A0.212200.654800.720500.0440*
H7B0.068100.638900.621400.0440*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I10.0578 (2)0.0421 (2)0.0529 (2)0.0132 (1)0.0143 (1)0.0003 (1)
S10.0304 (3)0.0232 (3)0.0442 (4)−0.0049 (3)−0.0027 (3)−0.0042 (3)
O10.0375 (12)0.0252 (10)0.0551 (14)−0.0047 (9)0.0058 (10)−0.0016 (9)
O20.0413 (13)0.0247 (11)0.0772 (18)0.0014 (9)0.0106 (12)0.0057 (11)
O30.0498 (14)0.0282 (11)0.0602 (16)−0.0014 (10)−0.0147 (12)−0.0130 (10)
O40.0337 (11)0.0411 (13)0.0565 (15)−0.0076 (10)0.0046 (10)−0.0034 (11)
N10.0353 (13)0.0217 (11)0.0466 (15)−0.0039 (9)−0.0051 (11)−0.0016 (10)
C10.0348 (15)0.0227 (12)0.0391 (16)0.0011 (11)−0.0065 (12)−0.0059 (11)
C20.0442 (17)0.0279 (14)0.0394 (17)0.0028 (12)−0.0029 (13)−0.0035 (12)
C30.063 (2)0.0326 (17)0.048 (2)−0.0015 (15)0.0038 (17)0.0022 (14)
C40.075 (3)0.0260 (16)0.054 (2)0.0038 (16)−0.009 (2)−0.0024 (14)
C50.062 (2)0.0287 (16)0.065 (2)0.0135 (15)−0.0084 (19)−0.0137 (16)
C60.0454 (18)0.0322 (16)0.052 (2)0.0049 (13)0.0002 (15)−0.0102 (14)
C70.0333 (15)0.0247 (13)0.0495 (18)−0.0027 (11)0.0011 (13)0.0018 (12)
C80.0343 (15)0.0229 (13)0.0449 (17)−0.0033 (11)−0.0040 (13)−0.0002 (12)

Geometric parameters (Å, °)

I1—C22.094 (3)C2—C31.388 (5)
S1—O31.429 (3)C3—C41.382 (5)
S1—O41.431 (2)C4—C51.369 (6)
S1—N11.613 (3)C5—C61.382 (5)
S1—C11.780 (3)C7—C81.509 (5)
O1—C81.212 (4)C3—H30.9300
O2—C81.310 (4)C4—H40.9300
O2—H2O0.8200C5—H50.9300
N1—C71.442 (4)C6—H60.9300
N1—H1N0.8600C7—H7A0.9700
C1—C61.389 (5)C7—H7B0.9700
C1—C21.385 (5)
O3—S1—O4118.92 (15)C1—C6—C5120.5 (4)
O3—S1—N1106.70 (15)N1—C7—C8115.3 (3)
O3—S1—C1109.54 (16)O1—C8—O2124.4 (3)
O4—S1—N1110.20 (14)O1—C8—C7124.5 (3)
O4—S1—C1105.65 (15)O2—C8—C7111.1 (3)
N1—S1—C1105.02 (13)C2—C3—H3120.00
C8—O2—H2O109.00C4—C3—H3120.00
S1—N1—C7121.8 (2)C3—C4—H4120.00
C7—N1—H1N119.00C5—C4—H4120.00
S1—N1—H1N119.00C4—C5—H5120.00
C2—C1—C6119.5 (3)C6—C5—H5120.00
S1—C1—C6116.4 (3)C1—C6—H6120.00
S1—C1—C2124.1 (2)C5—C6—H6120.00
I1—C2—C1124.6 (2)N1—C7—H7A108.00
I1—C2—C3116.0 (3)N1—C7—H7B108.00
C1—C2—C3119.5 (3)C8—C7—H7A108.00
C2—C3—C4120.5 (4)C8—C7—H7B108.00
C3—C4—C5120.1 (3)H7A—C7—H7B107.00
C4—C5—C6120.0 (4)
O3—S1—N1—C715.3 (3)C6—C1—C2—I1178.1 (3)
O4—S1—N1—C7−115.1 (3)C6—C1—C2—C3−1.5 (5)
C1—S1—N1—C7131.6 (3)S1—C1—C6—C5179.6 (3)
O3—S1—C1—C254.6 (3)C2—C1—C6—C51.3 (5)
O3—S1—C1—C6−123.6 (3)I1—C2—C3—C4−179.3 (3)
O4—S1—C1—C2−176.2 (3)C1—C2—C3—C40.3 (6)
O4—S1—C1—C65.6 (3)C2—C3—C4—C50.9 (6)
N1—S1—C1—C2−59.7 (3)C3—C4—C5—C6−1.1 (6)
N1—S1—C1—C6122.1 (3)C4—C5—C6—C1−0.1 (6)
S1—N1—C7—C872.2 (4)N1—C7—C8—O1−6.5 (5)
S1—C1—C2—I10.0 (4)N1—C7—C8—O2174.0 (3)
S1—C1—C2—C3−179.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.862.473.142 (3)135
O2—H2O···O1ii0.821.862.676 (4)176

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2093).

References

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