In the title compound, C
13H
11NO
4S, 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—H

O hydrogen-bonding interactions, while the crystal packing is stabilized by C—H

O and O—H

O hydrogen bonds and C—H

π interactions. The O—H

O hydrogen bonds form a cyclic dimer, with graph-set motif
R22(8), about a centre of symmetry.
Supporting information
CCDC reference: 738166
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.105
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
identifier.
brownish
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 29
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 7
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: The synthesis and characterization of the compound has been made
by A. M. Asiri and S. A. Khan. The diffraction data of the compound has been
collected by M. N. Arshad, I. U. Khan and H. M. A. Sharif. The crystallography
and preparation for publication have been carried out by M. Akkurt.
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
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).
2-Benzenesulfonamidobenzoic acid
top
Crystal data top
C13H11NO4S | F(000) = 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 = 2.5–23.4° |
b = 8.7223 (9) Å | µ = 0.27 mm−1 |
c = 11.0077 (10) Å | T = 296 K |
β = 106.149 (3)° | Prism, brownish black |
V = 2515.0 (4) Å3 | 0.36 × 0.26 × 0.11 mm |
Z = 8 | |
Data collection top
Bruker Kappa APEXII CCD area-detector diffractometer | 1824 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 27.9°, θmin = 2.5° |
ϕ and ω scans | h = −35→35 |
12048 measured reflections | k = −11→11 |
2989 independent reflections | l = −14→13 |
Refinement top
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.631P] where P = (Fo2 + 2Fc2)/3 |
2989 reflections | (Δ/σ)max < 0.001 |
173 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Crystal data top
C13H11NO4S | V = 2515.0 (4) Å3 |
Mr = 277.30 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
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)° | |
Data collection top
Bruker Kappa APEXII CCD area-detector diffractometer | 1824 reflections with I > 2σ(I) |
12048 measured reflections | Rint = 0.047 |
2989 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
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 |
173 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
Hydrogen-bond geometry (Å, º) top
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; (x) −x+3/2, −y+1/2, −z+1; (xii) x, y+1, z. |
Experimental details
Crystal data |
Chemical formula | C13H11NO4S |
Mr | 277.30 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 27.271 (3), 8.7223 (9), 11.0077 (10) |
β (°) | 106.149 (3) |
V (Å3) | 2515.0 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.36 × 0.26 × 0.11 |
|
Data collection |
Diffractometer | Bruker Kappa APEXII CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12048, 2989, 1824 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.659 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.105, 1.00 |
No. of reflections | 2989 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.25 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.8600 | 1.9900 | 2.644 (2) | 132.00 |
O4—H4···O3i | 0.8200 | 1.8900 | 2.712 (2) | 178.00 |
C5—H5···O1ii | 0.9300 | 2.4700 | 3.372 (3) | 162.00 |
C6—H6···O2 | 0.9300 | 2.5000 | 2.878 (3) | 104.00 |
C9—H9···O4 | 0.9300 | 2.3500 | 2.700 (3) | 102.00 |
C11—H11···O1iii | 0.9300 | 2.5500 | 3.429 (3) | 159.00 |
C12—H12···O2 | 0.9300 | 2.3700 | 3.032 (3) | 128.00 |
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. |
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.