Acta Cryst. (2009). E65, o549 [ doi:10.1107/S1600536809005248 ]
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-HO 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.
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.
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).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
![[Figure 1]](./su2093fig1thm.gif)
| Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. The thermal ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./su2093fig2thm.gif)
| Fig. 2. Crystal packing of the title compound, viewed along the axis, showing the intermolecular hydrogen bonds as dashed lines. |
| C8H8INO4S | Z = 2 |
| Mr = 341.11 | F(000) = 328 |
| Triclinic, P1 | Dx = 2.087 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 5.5877 (2) Å | Cell parameters from 6313 reflections |
| b = 8.0145 (2) Å | θ = 2.6–28.3° |
| c = 12.3584 (4) Å | µ = 3.14 mm−1 |
| 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 |
| Bruker Kappa APEXII CCD diffractometer | 2691 independent reflections |
| Radiation source: fine-focus sealed tube | 2297 reflections with I > 2σ(I) |
| graphite | Rint = 0.028 |
| φ and ω scans | θmax = 28.3°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −7→7 |
| Tmin = 0.691, Tmax = 0.834 | k = −10→10 |
| 11492 measured reflections | l = −16→16 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.086 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.6546P] where P = (Fo2 + 2Fc2)/3 |
| 2691 reflections | (Δ/σ)max = 0.001 |
| 137 parameters | Δρmax = 1.43 e Å−3 |
| 0 restraints | Δρmin = −1.09 e Å−3 |
| C8H8INO4S | γ = 88.038 (2)° |
| Mr = 341.11 | V = 542.81 (3) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 5.5877 (2) Å | Mo Kα radiation |
| b = 8.0145 (2) Å | µ = 3.14 mm−1 |
| c = 12.3584 (4) Å | T = 296 K |
| α = 80.923 (2)° | 0.22 × 0.10 × 0.06 mm |
| β = 83.398 (2)° |
| Bruker Kappa APEXII CCD diffractometer | 2691 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2297 reflections with I > 2σ(I) |
| Tmin = 0.691, Tmax = 0.834 | Rint = 0.028 |
| 11492 measured reflections | θmax = 28.3° |
| R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
| wR(F2) = 0.086 | Δρmax = 1.43 e Å−3 |
| S = 1.02 | Δρmin = −1.09 e Å−3 |
| 2691 reflections | Absolute structure: ? |
| 137 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| I1 | 0.10590 (5) | 0.34414 (3) | 0.90179 (2) | 0.0537 (1) | |
| S1 | 0.59293 (13) | 0.42594 (9) | 0.68657 (7) | 0.0327 (2) | |
| O1 | 0.5522 (4) | 0.7909 (3) | 0.5250 (2) | 0.0405 (7) | |
| O2 | 0.2240 (4) | 0.9320 (3) | 0.5837 (3) | 0.0506 (8) | |
| O3 | 0.6165 (5) | 0.5362 (3) | 0.7649 (2) | 0.0447 (8) | |
| O4 | 0.7874 (4) | 0.4121 (3) | 0.6022 (2) | 0.0448 (8) | |
| N1 | 0.3478 (5) | 0.4818 (3) | 0.6322 (2) | 0.0348 (8) | |
| C1 | 0.5418 (5) | 0.2165 (4) | 0.7568 (3) | 0.0319 (8) | |
| C2 | 0.3582 (6) | 0.1730 (4) | 0.8409 (3) | 0.0376 (9) | |
| C3 | 0.3352 (8) | 0.0057 (4) | 0.8907 (3) | 0.0496 (11) | |
| C4 | 0.4944 (8) | −0.1169 (4) | 0.8574 (3) | 0.0520 (13) | |
| C5 | 0.6787 (8) | −0.0735 (4) | 0.7758 (4) | 0.0514 (11) | |
| C6 | 0.7032 (7) | 0.0926 (4) | 0.7254 (3) | 0.0434 (10) | |
| C7 | 0.2290 (6) | 0.6417 (4) | 0.6433 (3) | 0.0371 (9) | |
| C8 | 0.3550 (6) | 0.7946 (4) | 0.5770 (3) | 0.0346 (9) | |
| H1N | 0.28640 | 0.41450 | 0.59550 | 0.0420* | |
| H2O | 0.29800 | 1.01380 | 0.54930 | 0.0760* | |
| H3 | 0.21160 | −0.02410 | 0.94690 | 0.0600* | |
| H4 | 0.47630 | −0.22890 | 0.89050 | 0.0630* | |
| H5 | 0.78740 | −0.15580 | 0.75430 | 0.0620* | |
| H6 | 0.82870 | 0.12170 | 0.67000 | 0.0520* | |
| H7A | 0.21220 | 0.65480 | 0.72050 | 0.0440* | |
| H7B | 0.06810 | 0.63890 | 0.62140 | 0.0440* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| I1 | 0.0578 (2) | 0.0421 (2) | 0.0529 (2) | 0.0132 (1) | 0.0143 (1) | 0.0003 (1) |
| S1 | 0.0304 (3) | 0.0232 (3) | 0.0442 (4) | −0.0049 (3) | −0.0027 (3) | −0.0042 (3) |
| O1 | 0.0375 (12) | 0.0252 (10) | 0.0551 (14) | −0.0047 (9) | 0.0058 (10) | −0.0016 (9) |
| O2 | 0.0413 (13) | 0.0247 (11) | 0.0772 (18) | 0.0014 (9) | 0.0106 (12) | 0.0057 (11) |
| O3 | 0.0498 (14) | 0.0282 (11) | 0.0602 (16) | −0.0014 (10) | −0.0147 (12) | −0.0130 (10) |
| O4 | 0.0337 (11) | 0.0411 (13) | 0.0565 (15) | −0.0076 (10) | 0.0046 (10) | −0.0034 (11) |
| N1 | 0.0353 (13) | 0.0217 (11) | 0.0466 (15) | −0.0039 (9) | −0.0051 (11) | −0.0016 (10) |
| C1 | 0.0348 (15) | 0.0227 (12) | 0.0391 (16) | 0.0011 (11) | −0.0065 (12) | −0.0059 (11) |
| C2 | 0.0442 (17) | 0.0279 (14) | 0.0394 (17) | 0.0028 (12) | −0.0029 (13) | −0.0035 (12) |
| C3 | 0.063 (2) | 0.0326 (17) | 0.048 (2) | −0.0015 (15) | 0.0038 (17) | 0.0022 (14) |
| C4 | 0.075 (3) | 0.0260 (16) | 0.054 (2) | 0.0038 (16) | −0.009 (2) | −0.0024 (14) |
| C5 | 0.062 (2) | 0.0287 (16) | 0.065 (2) | 0.0135 (15) | −0.0084 (19) | −0.0137 (16) |
| C6 | 0.0454 (18) | 0.0322 (16) | 0.052 (2) | 0.0049 (13) | 0.0002 (15) | −0.0102 (14) |
| C7 | 0.0333 (15) | 0.0247 (13) | 0.0495 (18) | −0.0027 (11) | 0.0011 (13) | 0.0018 (12) |
| C8 | 0.0343 (15) | 0.0229 (13) | 0.0449 (17) | −0.0033 (11) | −0.0040 (13) | −0.0002 (12) |
| I1—C2 | 2.094 (3) | C2—C3 | 1.388 (5) |
| S1—O3 | 1.429 (3) | C3—C4 | 1.382 (5) |
| S1—O4 | 1.431 (2) | C4—C5 | 1.369 (6) |
| S1—N1 | 1.613 (3) | C5—C6 | 1.382 (5) |
| S1—C1 | 1.780 (3) | C7—C8 | 1.509 (5) |
| O1—C8 | 1.212 (4) | C3—H3 | 0.9300 |
| O2—C8 | 1.310 (4) | C4—H4 | 0.9300 |
| O2—H2O | 0.8200 | C5—H5 | 0.9300 |
| N1—C7 | 1.442 (4) | C6—H6 | 0.9300 |
| N1—H1N | 0.8600 | C7—H7A | 0.9700 |
| C1—C6 | 1.389 (5) | C7—H7B | 0.9700 |
| C1—C2 | 1.385 (5) | ||
| O3—S1—O4 | 118.92 (15) | C1—C6—C5 | 120.5 (4) |
| O3—S1—N1 | 106.70 (15) | N1—C7—C8 | 115.3 (3) |
| O3—S1—C1 | 109.54 (16) | O1—C8—O2 | 124.4 (3) |
| O4—S1—N1 | 110.20 (14) | O1—C8—C7 | 124.5 (3) |
| O4—S1—C1 | 105.65 (15) | O2—C8—C7 | 111.1 (3) |
| N1—S1—C1 | 105.02 (13) | C2—C3—H3 | 120.00 |
| C8—O2—H2O | 109.00 | C4—C3—H3 | 120.00 |
| S1—N1—C7 | 121.8 (2) | C3—C4—H4 | 120.00 |
| C7—N1—H1N | 119.00 | C5—C4—H4 | 120.00 |
| S1—N1—H1N | 119.00 | C4—C5—H5 | 120.00 |
| C2—C1—C6 | 119.5 (3) | C6—C5—H5 | 120.00 |
| S1—C1—C6 | 116.4 (3) | C1—C6—H6 | 120.00 |
| S1—C1—C2 | 124.1 (2) | C5—C6—H6 | 120.00 |
| I1—C2—C1 | 124.6 (2) | N1—C7—H7A | 108.00 |
| I1—C2—C3 | 116.0 (3) | N1—C7—H7B | 108.00 |
| C1—C2—C3 | 119.5 (3) | C8—C7—H7A | 108.00 |
| C2—C3—C4 | 120.5 (4) | C8—C7—H7B | 108.00 |
| C3—C4—C5 | 120.1 (3) | H7A—C7—H7B | 107.00 |
| C4—C5—C6 | 120.0 (4) | ||
| O3—S1—N1—C7 | 15.3 (3) | C6—C1—C2—I1 | 178.1 (3) |
| O4—S1—N1—C7 | −115.1 (3) | C6—C1—C2—C3 | −1.5 (5) |
| C1—S1—N1—C7 | 131.6 (3) | S1—C1—C6—C5 | 179.6 (3) |
| O3—S1—C1—C2 | 54.6 (3) | C2—C1—C6—C5 | 1.3 (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—C4 | 0.3 (6) |
| O4—S1—C1—C6 | 5.6 (3) | C2—C3—C4—C5 | 0.9 (6) |
| N1—S1—C1—C2 | −59.7 (3) | C3—C4—C5—C6 | −1.1 (6) |
| N1—S1—C1—C6 | 122.1 (3) | C4—C5—C6—C1 | −0.1 (6) |
| S1—N1—C7—C8 | 72.2 (4) | N1—C7—C8—O1 | −6.5 (5) |
| S1—C1—C2—I1 | 0.0 (4) | N1—C7—C8—O2 | 174.0 (3) |
| S1—C1—C2—C3 | −179.6 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.86 | 2.47 | 3.142 (3) | 135 |
| O2—H2O···O1ii | 0.82 | 1.86 | 2.676 (4) | 176 |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.86 | 2.47 | 3.142 (3) | 135 |
| O2—H2O···O1ii | 0.82 | 1.86 | 2.676 (4) | 176 |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1. |
MNA acknowledges the Higher Education Commission, Pakistan, for providing a PhD Scholarship under PIN 042-120607-PS2-183.
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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.