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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 6| June 2009| Pages o1246-o1247
doi:10.1107/S1600536809016900

2-Benzenesulfonamido­benzoic acid

Abdullah Mohamed Asiri,a Mehmet Akkurt,b* Salman A. Khan,a Muhammad Nadeem Arshad,c Islam Ullah Khanc and Hafiz Muhammad Adeel Sharifc

aChemistry Department, Faculty of Science, King Abdul-Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, and cDepartment of Chemistry, Government College University, Lahore, Pakistan
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 5 May 2009; accepted 5 May 2009; online 14 May 2009)

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—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.

Related literature

For background to sulfonamide derivatives, see: Sheppard et al. (2006[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.]). For similar structures, see: Arshad et al. (2009[Arshad, M. N., Khan, I. U., Shafiq, M. & Mukhtar, A. (2009). Acta Cryst. E65, o549.]); Sethu Sankar et al. (2002[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.]); Wijeyesakere et al. (2008[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.]). For bond-length data, see: Allen et al. (1987[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.]). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data

  • C13H11NO4S

  • Mr = 277.30

  • Monoclinic, C 2/c

  • a = 27.271 (3) Å

  • b = 8.7223 (9) Å

  • c = 11.0077 (10) Å

  • β = 106.149 (3)°

  • V = 2515.0 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 296 K

  • 0.36 × 0.26 × 0.11 mm
Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: none

  • 12048 measured reflections

  • 2989 independent reflections

  • 1824 reflections with I > 2σ(I)

  • Rint = 0.047
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.105

  • S = 1.00

  • 2989 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x, y+1, z; (iv) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]. Cg2 is the centroid of the C7–C12 ring.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016900/fj2215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016900/fj2215Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

For background to sulfonamide derivatives, see: Sheppard et al. (2006). For similar structures, see: Arshad et al. (2009); Sethu Sankar et al. (2002); Wijeyesakere et al. (2008). For bond-lengthdata, see: Allen et al. (1987). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995); Etter (1990). Cg2 is the centroid of the C7–C12 ring.

Experimental top

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.

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. A view of the title compound showing the atom labelling scheme and displacement ellipsoids at the 30% probability level.
[Figure 2] 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] Fig. 3. The molecular packing for (I) viewed down the b axis.
2-Benzenesulfonamidobenzoic acid top
Crystal data top
C13H11NO4SF(000) = 1152
Mr = 277.30Dx = 1.465 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2374 reflections
a = 27.271 (3) Åθ = 2.5–23.4°
b = 8.7223 (9) ŵ = 0.27 mm−1
c = 11.0077 (10) ÅT = 296 K
β = 106.149 (3)°Prism, brownish black
V = 2515.0 (4) Å30.36 × 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 tubeRint = 0.047
Graphite monochromatorθmax = 27.9°, θmin = 2.5°
ϕ and ω scansh = −35→35
12048 measured reflectionsk = −11→11
2989 independent reflectionsl = −14→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-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 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C13H11NO4SV = 2515.0 (4) Å3
Mr = 277.30Z = 8
Monoclinic, C2/cMo Kα radiation
a = 27.271 (3) ŵ = 0.27 mm−1
b = 8.7223 (9) ÅT = 296 K
c = 11.0077 (10) Å0.36 × 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 reflectionsRint = 0.047
2989 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.00Δρmax = 0.34 e Å−3
2989 reflectionsΔρmin = −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
xyzUiso*/Ueq
S10.63178 (2)0.04792 (6)0.18228 (5)0.0404 (2)
O10.62113 (5)−0.11217 (17)0.16769 (14)0.0535 (6)
O20.63031 (6)0.13887 (18)0.07397 (13)0.0533 (5)
O30.53363 (5)0.03052 (18)0.39985 (13)0.0483 (5)
O40.50843 (6)0.2115 (2)0.51125 (16)0.0590 (6)
N10.59038 (6)0.11156 (19)0.25095 (17)0.0454 (6)
C10.69269 (7)0.0708 (2)0.28988 (18)0.0392 (7)
C20.70663 (9)−0.0206 (3)0.3954 (2)0.0588 (9)
C30.75548 (12)−0.0093 (4)0.4738 (2)0.0771 (11)
C40.78960 (10)0.0910 (4)0.4466 (3)0.0750 (10)
C50.77546 (9)0.1822 (3)0.3430 (3)0.0721 (11)
C60.72658 (9)0.1735 (3)0.2632 (2)0.0553 (8)
C70.58485 (7)0.2638 (2)0.28900 (18)0.0380 (6)
C80.55742 (7)0.2911 (2)0.37784 (18)0.0399 (7)
C90.55267 (9)0.4409 (3)0.4151 (2)0.0557 (8)
C100.57274 (10)0.5620 (3)0.3654 (2)0.0649 (10)
C110.59832 (10)0.5339 (3)0.2762 (2)0.0581 (9)
C120.60453 (9)0.3876 (3)0.2386 (2)0.0491 (8)
C130.53286 (7)0.1656 (3)0.42990 (19)0.0436 (7)
H10.569500.045200.265900.0540*
H20.68350−0.089000.413500.0700*
H30.76540−0.070100.545900.0930*
H40.496300.137000.538000.0890*
H4A0.822700.096600.499500.0900*
H50.798800.250700.325600.0870*
H60.716700.236200.192300.0660*
H90.535400.459700.475500.0670*
H100.569100.661700.391600.0780*
H110.611600.615500.241000.0700*
H120.622100.370800.178600.0590*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0407 (3)0.0349 (3)0.0494 (3)−0.0008 (2)0.0191 (2)−0.0065 (2)
O10.0497 (9)0.0363 (9)0.0768 (11)−0.0047 (7)0.0212 (8)−0.0151 (8)
O20.0633 (10)0.0550 (10)0.0458 (8)0.0050 (8)0.0220 (7)0.0022 (7)
O30.0485 (9)0.0503 (10)0.0520 (9)−0.0019 (7)0.0236 (7)0.0001 (7)
O40.0627 (11)0.0616 (11)0.0651 (10)0.0020 (9)0.0383 (8)−0.0051 (9)
N10.0422 (10)0.0327 (10)0.0695 (12)−0.0042 (8)0.0294 (8)−0.0062 (9)
C10.0426 (11)0.0361 (12)0.0444 (11)−0.0018 (9)0.0212 (9)−0.0038 (9)
C20.0610 (16)0.0687 (18)0.0498 (13)−0.0095 (13)0.0208 (12)0.0077 (12)
C30.079 (2)0.096 (2)0.0506 (15)0.0031 (17)0.0085 (14)0.0086 (14)
C40.0488 (15)0.091 (2)0.0768 (19)−0.0042 (15)0.0038 (13)−0.0190 (17)
C50.0482 (15)0.072 (2)0.096 (2)−0.0214 (13)0.0199 (14)−0.0026 (17)
C60.0518 (14)0.0486 (15)0.0687 (15)−0.0099 (11)0.0221 (12)0.0039 (12)
C70.0347 (10)0.0343 (11)0.0439 (11)0.0032 (8)0.0091 (8)−0.0035 (9)
C80.0371 (11)0.0422 (12)0.0394 (11)0.0042 (9)0.0092 (8)−0.0026 (9)
C90.0577 (14)0.0537 (15)0.0604 (14)0.0092 (12)0.0242 (11)−0.0096 (12)
C100.0754 (18)0.0400 (14)0.0830 (18)0.0097 (13)0.0280 (14)−0.0104 (13)
C110.0707 (16)0.0366 (14)0.0695 (16)0.0009 (12)0.0235 (13)0.0040 (11)
C120.0577 (14)0.0403 (13)0.0550 (13)0.0016 (10)0.0250 (11)−0.0002 (11)
C130.0355 (11)0.0547 (15)0.0399 (11)0.0077 (10)0.0093 (9)−0.0007 (11)
Geometric parameters (Å, º) top
S1—O11.4262 (16)C7—C81.407 (3)
S1—O21.4233 (16)C8—C131.479 (3)
S1—N11.6213 (18)C8—C91.386 (3)
S1—C11.763 (2)C9—C101.372 (4)
O3—C131.226 (3)C10—C111.375 (4)
O4—C131.318 (3)C11—C121.367 (4)
O4—H40.8200C2—H20.9300
N1—C71.413 (2)C3—H30.9300
N1—H10.8600C4—H4A0.9300
C1—C61.376 (3)C5—H50.9300
C1—C21.372 (3)C6—H60.9300
C2—C31.375 (4)C9—H90.9300
C3—C41.370 (5)C10—H100.9300
C4—C51.356 (4)C11—H110.9300
C5—C61.380 (4)C12—H120.9300
C7—C121.388 (3)
S1···H122.8300C13···O3iv3.408 (3)
O1···C13i3.059 (3)C13···C7vii3.541 (3)
O1···C5ii3.372 (3)C13···O1iii3.059 (3)
O1···O4i3.197 (2)C13···N1vii3.429 (3)
O2···C123.032 (3)C6···H3i3.0100
O2···C2i3.396 (3)C9···H9viii3.1000
O2···O3i3.162 (2)C11···H4Ax3.0100
O3···O2iii3.162 (2)C12···H4Ax3.0100
O3···O4iv2.712 (2)C13···H12.5200
O3···C13iv3.408 (3)C13···H4iv2.8100
O3···N12.644 (2)H1···O31.9900
O4···O3iv2.712 (2)H1···C132.5200
O4···O1iii3.197 (2)H1···O3vii2.9000
O1···H5ii2.4700H2···O12.7700
O1···H22.7700H2···O2iii2.6200
O1···H11v2.5500H3···C6iii3.0100
O2···H2i2.6200H4···O3iv1.8900
O2···H62.5000H4···C13iv2.8100
O2···H10vi2.8200H4···H4iv2.5600
O2···H122.3700H4A···C11x3.0100
O3···H1vii2.9000H4A···C12x3.0100
O3···H4iv1.8900H5···O1ix2.4700
O3···H11.9900H6···O22.5000
O4···H10viii2.8500H9···O42.3500
O4···H92.3500H9···C9viii3.1000
N1···O32.644 (2)H9···H9viii2.2600
N1···C13vii3.429 (3)H10···O4viii2.8500
C2···O2iii3.396 (3)H10···O2xi2.8200
C5···O1ix3.372 (3)H11···O1xii2.5500
C7···C13vii3.541 (3)H12···S12.8300
C8···C8vii3.581 (3)H12···O22.3700
C12···O23.032 (3)
O1—S1—O2119.60 (9)C9—C10—C11119.0 (2)
O1—S1—N1103.97 (9)C10—C11—C12120.9 (2)
O1—S1—C1108.11 (9)C7—C12—C11120.7 (2)
O2—S1—N1109.80 (10)O3—C13—O4121.7 (2)
O2—S1—C1107.54 (9)O3—C13—C8124.28 (18)
N1—S1—C1107.23 (9)O4—C13—C8114.0 (2)
C13—O4—H4109.00C1—C2—H2121.00
S1—N1—C7127.27 (14)C3—C2—H2121.00
C7—N1—H1116.00C2—C3—H3120.00
S1—N1—H1116.00C4—C3—H3120.00
C2—C1—C6121.0 (2)C3—C4—H4A120.00
S1—C1—C2119.36 (16)C5—C4—H4A120.00
S1—C1—C6119.58 (15)C4—C5—H5120.00
C1—C2—C3118.8 (2)C6—C5—H5120.00
C2—C3—C4120.5 (3)C1—C6—H6120.00
C3—C4—C5120.5 (3)C5—C6—H6120.00
C4—C5—C6120.1 (3)C8—C9—H9119.00
C1—C6—C5119.2 (2)C10—C9—H9119.00
C8—C7—C12119.04 (18)C9—C10—H10120.00
N1—C7—C12121.84 (19)C11—C10—H10120.00
N1—C7—C8119.10 (16)C10—C11—H11120.00
C7—C8—C9118.47 (18)C12—C11—H11120.00
C7—C8—C13121.97 (17)C7—C12—H12120.00
C9—C8—C13119.55 (19)C11—C12—H12120.00
C8—C9—C10121.8 (2)
O1—S1—N1—C7178.91 (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—C764.56 (19)N1—C7—C8—C9179.46 (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—C270.63 (19)C12—C7—C8—C13176.42 (19)
O1—S1—C1—C6135.31 (17)N1—C7—C12—C11179.5 (2)
O2—S1—C1—C64.9 (2)C8—C7—C12—C111.3 (3)
N1—S1—C1—C6−113.14 (18)C7—C8—C9—C101.7 (3)
S1—N1—C7—C8−161.98 (16)C13—C8—C9—C10−177.0 (2)
S1—N1—C7—C1219.8 (3)C7—C8—C13—O3−1.0 (3)
S1—C1—C2—C3175.4 (2)C7—C8—C13—O4−179.52 (18)
C2—C1—C6—C51.1 (3)C9—C8—C13—O3177.7 (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—C51.0 (5)C10—C11—C12—C70.4 (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···AD—HH···AD···AD—H···A
N1—H1···O30.861.992.644 (2)132
O4—H4···O3iv0.821.892.712 (2)178
C5—H5···O1ix0.932.473.372 (3)162
C6—H6···O20.932.502.878 (3)104
C9—H9···O40.932.352.700 (3)102
C11—H11···O1xii0.932.553.429 (3)159
C12—H12···O20.932.373.032 (3)128
C4—H4A···Cg2x0.932.843.765 (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 formulaC13H11NO4S
Mr277.30
Crystal system, space groupMonoclinic, 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)
Z8
Radiation typeMo Kα
µ (mm−1)0.27
Crystal size (mm)0.36 × 0.26 × 0.11
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		12048, 2989, 1824
Rint0.047
(sin θ/λ)max (Å−1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.105, 1.00
No. of reflections2989
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.34, −0.25

Computer programs: APEX2 (Bruker, 2007), SAINT2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.86001.99002.644 (2)132.00
O4—H4···O3i0.82001.89002.712 (2)178.00
C5—H5···O1ii0.93002.47003.372 (3)162.00
C6—H6···O20.93002.50002.878 (3)104.00
C9—H9···O40.93002.35002.700 (3)102.00
C11—H11···O1iii0.93002.55003.429 (3)159.00
C12—H12···O20.93002.37003.032 (3)128.00
C4—H4A···Cg2iv0.932.843.765 (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.
 

Acknowledgements

AMA acknowledges the Chemistry Department, Faculty of Science, King Abdul-Aziz University, for providing laboratories and facilities.

References

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ISSN: 2056-9890
Volume 65| Part 6| June 2009| Pages o1246-o1247
doi:10.1107/S1600536809016900
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