Acta Cryst. (2009). E65, o1246-o1247 [ doi:10.1107/S1600536809016900 ]
In the title compound, C13H11NO4S, the dihedral angle between the planes of the benzene ring and the carboxyl group is 13.7 (1)°. The molecular structure contains intramolecular N-H
O and C-HO hydrogen-bonding interactions, while the crystal packing is stabilized by C-HO and O-HO hydrogen bonds and C-H![[pi]](/logos/entities/pi_rmgif.gif)
interactions. The O-HO hydrogen bonds form a cyclic dimer, with graph-set motif R22(8), about a centre of symmetry.
Anthranilic acid (1 g, 7.3 mmol) was dissolved in distilled water (10 ml) in a round bottom flask (25 ml). The pH of the solution was maintained at 8–9 using 1M, Na2CO3. Benzene sulfonylchloride (1.29 g, 7.3 mmol) was then added to the above solution and stirred atroom temperature until all the benzene sulfonyl chloride was consumed. On completion of the reaction the pH was adjusted 1–2, using 1 N HCl. The precipitate obtained was filtered, washed with distilled water, dried and recrystalized in methanol to yield brownish black crystals.
All H atoms are clearly observed using the X-ray difference Fourier maps. H atoms were fixed geometrically and treated as riding, with C—H = 0.93 Å, N—H = 0.86 Å and O—H = 0.82 Å, with Uiso(H) = 1.2Ueq(C,N) and Uiso(H) = 1.5Ueq(O).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT2 (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); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
![[Figure 1]](./fj2215fig1thm.gif)
| Fig. 1. A view of the title compound showing the atom labelling scheme and displacement ellipsoids at the 30% probability level. |
![[Figure 2]](./fj2215fig2thm.gif)
| Fig. 2. View of the hydrogen bonding interactions of (I) in the unit cell. Hydrogen bonds are indicated by dashed lines and H atoms not involved in the shown interactions have been omitted for clarity. |
![[Figure 3]](./fj2215fig3thm.gif)
| Fig. 3. The molecular packing for (I) viewed down the b axis. |
| C13H11NO4S | F000 = 1152 |
| Mr = 277.30 | Dx = 1.465 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 2374 reflections |
| a = 27.271 (3) Å | θ = 2.5–23.4º |
| b = 8.7223 (9) Å | µ = 0.27 mm−1 |
| c = 11.0077 (10) Å | T = 296 K |
| β = 106.149 (3)º | Prism, brownish black |
| V = 2515.0 (4) Å3 | 0.36 × 0.26 × 0.11 mm |
| Z = 8 |
| Bruker Kappa APEXII CCD area-detector diffractometer | 1824 reflections with I > 2σ(I) |
| Radiation source: sealed tube | Rint = 0.047 |
| Monochromator: graphite | θmax = 27.9º |
| T = 296 K | θmin = 2.5º |
| φ and ω scans | h = −35→35 |
| Absorption correction: none | k = −11→11 |
| 12048 measured reflections | l = −14→13 |
| 2989 independent reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.631P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max < 0.001 |
| 2989 reflections | Δρmax = 0.34 e Å−3 |
| 173 parameters | Δρmin = −0.25 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C13H11NO4S | V = 2515.0 (4) Å3 |
| Mr = 277.30 | Z = 8 |
| Monoclinic, C2/c | Mo Kα |
| a = 27.271 (3) Å | µ = 0.27 mm−1 |
| b = 8.7223 (9) Å | T = 296 K |
| c = 11.0077 (10) Å | 0.36 × 0.26 × 0.11 mm |
| β = 106.149 (3)º |
| Bruker Kappa APEXII CCD area-detector diffractometer | 2989 independent reflections |
| Absorption correction: none | 1824 reflections with I > 2σ(I) |
| 12048 measured reflections | Rint = 0.047 |
| R[F2 > 2σ(F2)] = 0.041 | 173 parameters |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 1.00 | Δρmax = 0.34 e Å−3 |
| 2989 reflections | Δρmin = −0.25 e Å−3 |
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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
| S1 | 0.63178 (2) | 0.04792 (6) | 0.18228 (5) | 0.0404 (2) | |
| O1 | 0.62113 (5) | −0.11217 (17) | 0.16769 (14) | 0.0535 (6) | |
| O2 | 0.63031 (6) | 0.13887 (18) | 0.07397 (13) | 0.0533 (5) | |
| O3 | 0.53363 (5) | 0.03052 (18) | 0.39985 (13) | 0.0483 (5) | |
| O4 | 0.50843 (6) | 0.2115 (2) | 0.51125 (16) | 0.0590 (6) | |
| N1 | 0.59038 (6) | 0.11156 (19) | 0.25095 (17) | 0.0454 (6) | |
| C1 | 0.69269 (7) | 0.0708 (2) | 0.28988 (18) | 0.0392 (7) | |
| C2 | 0.70663 (9) | −0.0206 (3) | 0.3954 (2) | 0.0588 (9) | |
| C3 | 0.75548 (12) | −0.0093 (4) | 0.4738 (2) | 0.0771 (11) | |
| C4 | 0.78960 (10) | 0.0910 (4) | 0.4466 (3) | 0.0750 (10) | |
| C5 | 0.77546 (9) | 0.1822 (3) | 0.3430 (3) | 0.0721 (11) | |
| C6 | 0.72658 (9) | 0.1735 (3) | 0.2632 (2) | 0.0553 (8) | |
| C7 | 0.58485 (7) | 0.2638 (2) | 0.28900 (18) | 0.0380 (6) | |
| C8 | 0.55742 (7) | 0.2911 (2) | 0.37784 (18) | 0.0399 (7) | |
| C9 | 0.55267 (9) | 0.4409 (3) | 0.4151 (2) | 0.0557 (8) | |
| C10 | 0.57274 (10) | 0.5620 (3) | 0.3654 (2) | 0.0649 (10) | |
| C11 | 0.59832 (10) | 0.5339 (3) | 0.2762 (2) | 0.0581 (9) | |
| C12 | 0.60453 (9) | 0.3876 (3) | 0.2386 (2) | 0.0491 (8) | |
| C13 | 0.53286 (7) | 0.1656 (3) | 0.42990 (19) | 0.0436 (7) | |
| H1 | 0.56950 | 0.04520 | 0.26590 | 0.0540* | |
| H2 | 0.68350 | −0.08900 | 0.41350 | 0.0700* | |
| H3 | 0.76540 | −0.07010 | 0.54590 | 0.0930* | |
| H4 | 0.49630 | 0.13700 | 0.53800 | 0.0890* | |
| H4A | 0.82270 | 0.09660 | 0.49950 | 0.0900* | |
| H5 | 0.79880 | 0.25070 | 0.32560 | 0.0870* | |
| H6 | 0.71670 | 0.23620 | 0.19230 | 0.0660* | |
| H9 | 0.53540 | 0.45970 | 0.47550 | 0.0670* | |
| H10 | 0.56910 | 0.66170 | 0.39160 | 0.0780* | |
| H11 | 0.61160 | 0.61550 | 0.24100 | 0.0700* | |
| H12 | 0.62210 | 0.37080 | 0.17860 | 0.0590* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0407 (3) | 0.0349 (3) | 0.0494 (3) | −0.0008 (2) | 0.0191 (2) | −0.0065 (2) |
| O1 | 0.0497 (9) | 0.0363 (9) | 0.0768 (11) | −0.0047 (7) | 0.0212 (8) | −0.0151 (8) |
| O2 | 0.0633 (10) | 0.0550 (10) | 0.0458 (8) | 0.0050 (8) | 0.0220 (7) | 0.0022 (7) |
| O3 | 0.0485 (9) | 0.0503 (10) | 0.0520 (9) | −0.0019 (7) | 0.0236 (7) | 0.0001 (7) |
| O4 | 0.0627 (11) | 0.0616 (11) | 0.0651 (10) | 0.0020 (9) | 0.0383 (8) | −0.0051 (9) |
| N1 | 0.0422 (10) | 0.0327 (10) | 0.0695 (12) | −0.0042 (8) | 0.0294 (8) | −0.0062 (9) |
| C1 | 0.0426 (11) | 0.0361 (12) | 0.0444 (11) | −0.0018 (9) | 0.0212 (9) | −0.0038 (9) |
| C2 | 0.0610 (16) | 0.0687 (18) | 0.0498 (13) | −0.0095 (13) | 0.0208 (12) | 0.0077 (12) |
| C3 | 0.079 (2) | 0.096 (2) | 0.0506 (15) | 0.0031 (17) | 0.0085 (14) | 0.0086 (14) |
| C4 | 0.0488 (15) | 0.091 (2) | 0.0768 (19) | −0.0042 (15) | 0.0038 (13) | −0.0190 (17) |
| C5 | 0.0482 (15) | 0.072 (2) | 0.096 (2) | −0.0214 (13) | 0.0199 (14) | −0.0026 (17) |
| C6 | 0.0518 (14) | 0.0486 (15) | 0.0687 (15) | −0.0099 (11) | 0.0221 (12) | 0.0039 (12) |
| C7 | 0.0347 (10) | 0.0343 (11) | 0.0439 (11) | 0.0032 (8) | 0.0091 (8) | −0.0035 (9) |
| C8 | 0.0371 (11) | 0.0422 (12) | 0.0394 (11) | 0.0042 (9) | 0.0092 (8) | −0.0026 (9) |
| C9 | 0.0577 (14) | 0.0537 (15) | 0.0604 (14) | 0.0092 (12) | 0.0242 (11) | −0.0096 (12) |
| C10 | 0.0754 (18) | 0.0400 (14) | 0.0830 (18) | 0.0097 (13) | 0.0280 (14) | −0.0104 (13) |
| C11 | 0.0707 (16) | 0.0366 (14) | 0.0695 (16) | 0.0009 (12) | 0.0235 (13) | 0.0040 (11) |
| C12 | 0.0577 (14) | 0.0403 (13) | 0.0550 (13) | 0.0016 (10) | 0.0250 (11) | −0.0002 (11) |
| C13 | 0.0355 (11) | 0.0547 (15) | 0.0399 (11) | 0.0077 (10) | 0.0093 (9) | −0.0007 (11) |
| S1—O1 | 1.4262 (16) | C7—C8 | 1.407 (3) |
| S1—O2 | 1.4233 (16) | C8—C13 | 1.479 (3) |
| S1—N1 | 1.6213 (18) | C8—C9 | 1.386 (3) |
| S1—C1 | 1.763 (2) | C9—C10 | 1.372 (4) |
| O3—C13 | 1.226 (3) | C10—C11 | 1.375 (4) |
| O4—C13 | 1.318 (3) | C11—C12 | 1.367 (4) |
| O4—H4 | 0.8200 | C2—H2 | 0.9300 |
| N1—C7 | 1.413 (2) | C3—H3 | 0.9300 |
| N1—H1 | 0.8600 | C4—H4A | 0.9300 |
| C1—C6 | 1.376 (3) | C5—H5 | 0.9300 |
| C1—C2 | 1.372 (3) | C6—H6 | 0.9300 |
| C2—C3 | 1.375 (4) | C9—H9 | 0.9300 |
| C3—C4 | 1.370 (5) | C10—H10 | 0.9300 |
| C4—C5 | 1.356 (4) | C11—H11 | 0.9300 |
| C5—C6 | 1.380 (4) | C12—H12 | 0.9300 |
| C7—C12 | 1.388 (3) | ||
| S1···H12 | 2.8300 | C13···O3iv | 3.408 (3) |
| O1···C13i | 3.059 (3) | C13···C7vii | 3.541 (3) |
| O1···C5ii | 3.372 (3) | C13···O1iii | 3.059 (3) |
| O1···O4i | 3.197 (2) | C13···N1vii | 3.429 (3) |
| O2···C12 | 3.032 (3) | C6···H3i | 3.0100 |
| O2···C2i | 3.396 (3) | C9···H9viii | 3.1000 |
| O2···O3i | 3.162 (2) | C11···H4Ax | 3.0100 |
| O3···O2iii | 3.162 (2) | C12···H4Ax | 3.0100 |
| O3···O4iv | 2.712 (2) | C13···H1 | 2.5200 |
| O3···C13iv | 3.408 (3) | C13···H4iv | 2.8100 |
| O3···N1 | 2.644 (2) | H1···O3 | 1.9900 |
| O4···O3iv | 2.712 (2) | H1···C13 | 2.5200 |
| O4···O1iii | 3.197 (2) | H1···O3vii | 2.9000 |
| O1···H5ii | 2.4700 | H2···O1 | 2.7700 |
| O1···H2 | 2.7700 | H2···O2iii | 2.6200 |
| O1···H11v | 2.5500 | H3···C6iii | 3.0100 |
| O2···H2i | 2.6200 | H4···O3iv | 1.8900 |
| O2···H6 | 2.5000 | H4···C13iv | 2.8100 |
| O2···H10vi | 2.8200 | H4···H4iv | 2.5600 |
| O2···H12 | 2.3700 | H4A···C11x | 3.0100 |
| O3···H1vii | 2.9000 | H4A···C12x | 3.0100 |
| O3···H4iv | 1.8900 | H5···O1ix | 2.4700 |
| O3···H1 | 1.9900 | H6···O2 | 2.5000 |
| O4···H10viii | 2.8500 | H9···O4 | 2.3500 |
| O4···H9 | 2.3500 | H9···C9viii | 3.1000 |
| N1···O3 | 2.644 (2) | H9···H9viii | 2.2600 |
| N1···C13vii | 3.429 (3) | H10···O4viii | 2.8500 |
| C2···O2iii | 3.396 (3) | H10···O2xi | 2.8200 |
| C5···O1ix | 3.372 (3) | H11···O1xii | 2.5500 |
| C7···C13vii | 3.541 (3) | H12···S1 | 2.8300 |
| C8···C8vii | 3.581 (3) | H12···O2 | 2.3700 |
| C12···O2 | 3.032 (3) | ||
| O1—S1—O2 | 119.60 (9) | C9—C10—C11 | 119.0 (2) |
| O1—S1—N1 | 103.97 (9) | C10—C11—C12 | 120.9 (2) |
| O1—S1—C1 | 108.11 (9) | C7—C12—C11 | 120.7 (2) |
| O2—S1—N1 | 109.80 (10) | O3—C13—O4 | 121.7 (2) |
| O2—S1—C1 | 107.54 (9) | O3—C13—C8 | 124.28 (18) |
| N1—S1—C1 | 107.23 (9) | O4—C13—C8 | 114.0 (2) |
| C13—O4—H4 | 109.00 | C1—C2—H2 | 121.00 |
| S1—N1—C7 | 127.27 (14) | C3—C2—H2 | 121.00 |
| C7—N1—H1 | 116.00 | C2—C3—H3 | 120.00 |
| S1—N1—H1 | 116.00 | C4—C3—H3 | 120.00 |
| C2—C1—C6 | 121.0 (2) | C3—C4—H4A | 120.00 |
| S1—C1—C2 | 119.36 (16) | C5—C4—H4A | 120.00 |
| S1—C1—C6 | 119.58 (15) | C4—C5—H5 | 120.00 |
| C1—C2—C3 | 118.8 (2) | C6—C5—H5 | 120.00 |
| C2—C3—C4 | 120.5 (3) | C1—C6—H6 | 120.00 |
| C3—C4—C5 | 120.5 (3) | C5—C6—H6 | 120.00 |
| C4—C5—C6 | 120.1 (3) | C8—C9—H9 | 119.00 |
| C1—C6—C5 | 119.2 (2) | C10—C9—H9 | 119.00 |
| C8—C7—C12 | 119.04 (18) | C9—C10—H10 | 120.00 |
| N1—C7—C12 | 121.84 (19) | C11—C10—H10 | 120.00 |
| N1—C7—C8 | 119.10 (16) | C10—C11—H11 | 120.00 |
| C7—C8—C9 | 118.47 (18) | C12—C11—H11 | 120.00 |
| C7—C8—C13 | 121.97 (17) | C7—C12—H12 | 120.00 |
| C9—C8—C13 | 119.55 (19) | C11—C12—H12 | 120.00 |
| C8—C9—C10 | 121.8 (2) | ||
| O1—S1—N1—C7 | 178.91 (17) | C3—C4—C5—C6 | −0.7 (5) |
| O2—S1—N1—C7 | −52.0 (2) | C4—C5—C6—C1 | −0.4 (4) |
| C1—S1—N1—C7 | 64.56 (19) | N1—C7—C8—C9 | 179.46 (19) |
| O1—S1—C1—C2 | −40.9 (2) | N1—C7—C8—C13 | −1.8 (3) |
| O2—S1—C1—C2 | −171.34 (17) | C12—C7—C8—C9 | −2.3 (3) |
| N1—S1—C1—C2 | 70.63 (19) | C12—C7—C8—C13 | 176.42 (19) |
| O1—S1—C1—C6 | 135.31 (17) | N1—C7—C12—C11 | 179.5 (2) |
| O2—S1—C1—C6 | 4.9 (2) | C8—C7—C12—C11 | 1.3 (3) |
| N1—S1—C1—C6 | −113.14 (18) | C7—C8—C9—C10 | 1.7 (3) |
| S1—N1—C7—C8 | −161.98 (16) | C13—C8—C9—C10 | −177.0 (2) |
| S1—N1—C7—C12 | 19.8 (3) | C7—C8—C13—O3 | −1.0 (3) |
| S1—C1—C2—C3 | 175.4 (2) | C7—C8—C13—O4 | −179.52 (18) |
| C2—C1—C6—C5 | 1.1 (3) | C9—C8—C13—O3 | 177.7 (2) |
| C6—C1—C2—C3 | −0.8 (4) | C9—C8—C13—O4 | −0.8 (3) |
| S1—C1—C6—C5 | −175.07 (19) | C8—C9—C10—C11 | −0.1 (4) |
| C1—C2—C3—C4 | −0.3 (4) | C9—C10—C11—C12 | −1.0 (4) |
| C2—C3—C4—C5 | 1.0 (5) | C10—C11—C12—C7 | 0.4 (4) |
| Symmetry codes: (i) x, −y, z−1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x, −y, z+1/2; (iv) −x+1, −y, −z+1; (v) x, y−1, z; (vi) x, −y+1, z−1/2; (vii) −x+1, y, −z+1/2; (viii) −x+1, −y+1, −z+1; (ix) −x+3/2, y+1/2, −z+1/2; (x) −x+3/2, −y+1/2, −z+1; (xi) x, −y+1, z+1/2; (xii) x, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O3 | 0.86 | 1.99 | 2.644 (2) | 132 |
| O4—H4···O3iv | 0.82 | 1.89 | 2.712 (2) | 178 |
| C5—H5···O1ix | 0.93 | 2.47 | 3.372 (3) | 162 |
| C6—H6···O2 | 0.93 | 2.50 | 2.878 (3) | 104 |
| C9—H9···O4 | 0.93 | 2.35 | 2.700 (3) | 102 |
| C11—H11···O1xii | 0.93 | 2.55 | 3.429 (3) | 159 |
| C12—H12···O2 | 0.93 | 2.37 | 3.032 (3) | 128 |
| C4—H4A···Cg2x | 0.93 | 2.84 | 3.765 (3) | 174 |
| Symmetry codes: (iv) −x+1, −y, −z+1; (ix) −x+3/2, y+1/2, −z+1/2; (xii) x, y+1, z; (x) −x+3/2, −y+1/2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O3 | 0.86 | 1.99 | 2.644 (2) | 132 |
| O4—H4···O3i | 0.82 | 1.89 | 2.712 (2) | 178 |
| C5—H5···O1ii | 0.93 | 2.47 | 3.372 (3) | 162 |
| C6—H6···O2 | 0.93 | 2.50 | 2.878 (3) | 104 |
| C9—H9···O4 | 0.93 | 2.35 | 2.700 (3) | 102 |
| C11—H11···O1iii | 0.93 | 2.55 | 3.429 (3) | 159 |
| C12—H12···O2 | 0.93 | 2.37 | 3.032 (3) | 128 |
| C4—H4A···Cg2iv | 0.93 | 2.84 | 3.765 (3) | 174 |
| Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) −x+3/2, −y+1/2, −z+1. |
AMA acknowledges the Chemistry Department, Faculty of Science, King Abdul-Aziz University, for providing laboratories and facilities.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Arshad, M. N., Khan, I. U., Shafiq, M. & Mukhtar, A. (2009). Acta Cryst. E65, o549.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Sethu Sankar, K., Velmurugan, D., Thirumamagal, B. T. S., Shanmuga Sundara Raj, S., Fun, H.-K. & Moon, J.-K. (2002). Acta Cryst. C58, o257–o259.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Sheppard, G. S., Wang, J., Kawai, M., Fidanze, S. D., Bamaung, N. Y., Erickson, S. A., Barnes, D. M., Tedrow, J. S., Kolaczkowski, L., Vasudevan, A., Park, D. C., Wang, G. T., Sanders, W. J., Mantei, R. A., Palazzo, F., Tucker-Garcia, L., Lou, P. P., Zhang, Q., Park, C. H., Kim, K. H., Petros, A., Olejniczak, E., Nettesheim, D., Hajduk, P., Henkin, J., Lesniewski, R., Davidsen, S. K. & Bell, R. L. (2006). J. Med. Chem. 49, 3832–3849.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Wijeyesakere, S. J., Nasser, F. A., Kampf, J. W., Aksinenko, A. Y., Sokolov, V. B., Malygin, V. V., Makhaeva, G. F. & Richardson, R. J. (2008). Acta Cryst. E64, o1425.
The title compound is sulfonamide derivative and prepared by the simple condensation of anthranilic acid and benzene sulfonylchloride. The anthranilic sulfonamide derivative has been investigated as an inhibitors of Methionine aminopeptidase-2 (MetAP2), a novel target for cancer therapy (Sheppard et al. 2006). The title compound is reported as in countinuation of our studies on the synthesis of sulfonamide derivatives (Arshad et al., 2009).
In the compound, (I), (Fig. 1), the C—O distances are as expected. The S—CPh distance of 1.763 (2)Å compare well with the literature value of 1.763 (9)Å (Allen et al., 1987). The S1—N1 distance of 1.6213 (18) Å is shorter than the literature value of 1.6458 (11) Å (Wijeyesakere et al., 2008). The mean S=O distance of 1.4248 (16) Å is comparable with the reported value of 1.436 (2)Å (Sethu Sankar et al., 2002). The interplanar angle between the phenyl rings in (I) is 89.01 (12)°. The slight increases in the N1—C7—C8 [119.10 (16)°] and C7—C8—C13 [121.97 (17)°] angles, from the ideal value of 120°, can be attributed to the steric interaction of the N1 and C13 substituents.
The molecular structures are stabilized by intramolecular N—H···O and C—H···O hydrogen bonding interactions. The crystal packing is stabilized by C—H···O and O—H···O hydrogen bonds, and C—H···π interactions (Table 1). The O—H···O hydrogen bond forms a cyclic dimer, with graph-set motif R22(8), about a centre of symmetry (Fig. 2). Fig. 3 shows the molecular packing for (I) viewed down the b axis.