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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1610–o1611.
Published online 2009 June 17. doi:  10.1107/S1600536809022545
PMCID: PMC2969408

2-(4-Bromo­benzene­sulfonamido)benzoic acid

Abstract

In the title compound, C13H10BrNO4S, the dihedral angle between the benzene rings is 82.75 (15)°. An intra­molecular N—H(...)O hydrogen bond generates an S(6) ring motif. In the crystal structure, two mol­ecules form an R 2 2(8) centrosymmetric dimer through a pair of O—H(...)O hydrogen bonds. Intra- and inter­molecular C—H(...)O hydrogen bonds are also observed.

Related literature

For background to sulfonamide derivatives, see: Allison et al. (2006 [triangle]); Sheppard et al. (2006 [triangle]). For related structures, see: Arshad et al. (2009 [triangle]); Shafiq et al. (2009 [triangle]); Asiri et al. (2009 [triangle]). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995 [triangle]); Etter (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1610-scheme1.jpg

Experimental

Crystal data

  • C13H10BrNO4S
  • M r = 356.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1610-efi2.jpg
  • a = 27.8316 (11) Å
  • b = 8.5684 (4) Å
  • c = 11.6632 (5) Å
  • β = 98.196 (2)°
  • V = 2752.9 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.15 mm−1
  • T = 296 K
  • 0.23 × 0.19 × 0.11 mm

Data collection

  • Bruker Kappa-APEXII CCD area-detector diffractometer
  • Absorption correction: refined from ΔF [Cubic fit to sin(θ)/λ - 24 parameters; Parkin et al., 1995 [triangle]] T min = 0.497, T max = 0.707
  • 14822 measured reflections
  • 3416 independent reflections
  • 1764 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.093
  • S = 0.98
  • 3416 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022545/is2431sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022545/is2431Isup2.hkl

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

Acknowledgments

The authors MNA, IUK, MS and GM acknowledge the Higher Education Commission, Pakistan, for support under the indigenous PhD 5000 Fellowship Programme.

supplementary crystallographic information

Comment

Sulfonamides are biologically active organic compounds. The anthranilic sulfonamide derivative has been reported as inhibitors of Methionine aminopeptidase-2 (MetAP2) (Sheppard et al., 2006) and halogenated anthranilic sulfonamide derivatives have been identified as novel, selective Cholecystokinin-2 Receptor Antagonists (Allison et al., 2006). The title compound is halogenated sulfonamide in countinuation of our studies on the synthesis of sulfonamide derivatives (Arshad et al., 2009) and benzothiazines (Shafiq et al., 2009).

In the title compound, (I), (Fig. 1), the values of the geometric parameters are normal, and they are comparable with those in the reported structure of the isomorf compound 2-benzenesulfonamidobenzoic acid (Asiri et al., 2009). The angle between the benzene rings is 82.75 (15)°.

The crystal packing is stabilized by C—H···O and O—H···O hydrogen bonds (Table 1). The intramolecular N—H···O hydrogen bond generates a graph set motif S(6). The O—H···O hydrogen bond forms a cyclic dimer, with a R22(8) motif (Bernstein et al., 1995; Etter, 1990), about a inversion centre (Fig. 2). Figure 3 shows the molecular packing for (I) viewed down the b axis, generating a zigzag layer running along the a axis.

Experimental

Anthranilic acid (2 g, 14.6 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. 4- Bromobenzene sulfonylchloride (3.72 g, 14.6 mmol) was suspended to the above solution and stirred at room temperature until all the 4-bromobenzene sulfonyl chloride was consumed. Progress of the reaction was observed by disappearing of suspension to clear solution. 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 recrystallized in methanol to yield dark brown crystals.

Refinement

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, and with Uiso(H) = 1.2Ueq(C, N) and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
View of the title molecule showing the atom labelling scheme and displacement ellipsoids at the 30% probability level.
Fig. 2.
View of the dimeric structure of (I). Hydrogen bonds are indicated by dashed lines. The atom labelled with the suffix a is generated by the symmetry operator (3/2 - x,1/2 - y,1 - z).
Fig. 3.
The molecular packing and hydrogen bonding for (I), viewed down the b axis. Hydrogen atoms not involved in the showed interactions have been omitted for clarity.

Crystal data

C13H10BrNO4SF(000) = 1424
Mr = 356.19Dx = 1.719 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3121 reflections
a = 27.8316 (11) Åθ = 2.5–22.0°
b = 8.5684 (4) ŵ = 3.15 mm1
c = 11.6632 (5) ÅT = 296 K
β = 98.196 (2)°Block, dark brown
V = 2752.9 (2) Å30.23 × 0.19 × 0.11 mm
Z = 8

Data collection

Bruker Kappa-APEXII CCD area-detector diffractometer3416 independent reflections
Radiation source: sealed tube1764 reflections with I > 2σ(I)
graphiteRint = 0.042
[var phi] and ω scansθmax = 28.3°, θmin = 2.5°
Absorption correction: part of the refinement model (ΔF) [Cubic fit to sin(θ)/λ - 24 parameters; Parkin et al., 1995]h = −37→36
Tmin = 0.497, Tmax = 0.707k = −11→11
14822 measured reflectionsl = −15→15

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 0.98w = 1/[σ2(Fo2) + (0.033P)2 + 1.5317P] where P = (Fo2 + 2Fc2)/3
3416 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.29 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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F^2^ 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 F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > σ(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Br10.81917 (1)0.43825 (6)0.51473 (4)0.1153 (2)
S10.62425 (3)0.44674 (8)0.15544 (6)0.0547 (2)
O10.53281 (7)0.4722 (2)0.39261 (16)0.0628 (7)
O20.50891 (7)0.2889 (2)0.50674 (17)0.0721 (8)
O30.61345 (8)0.6071 (2)0.13563 (17)0.0713 (8)
O40.63014 (7)0.3473 (2)0.06120 (15)0.0665 (7)
N10.58022 (7)0.3824 (2)0.22029 (18)0.0555 (8)
C10.67716 (9)0.4336 (3)0.2571 (2)0.0514 (9)
C20.71403 (11)0.3319 (3)0.2413 (3)0.0659 (11)
C30.75605 (11)0.3324 (4)0.3185 (3)0.0788 (14)
C40.76082 (11)0.4310 (4)0.4111 (3)0.0705 (11)
C50.72375 (12)0.5304 (4)0.4281 (3)0.0782 (14)
C60.68182 (12)0.5303 (4)0.3517 (3)0.0714 (12)
C70.57612 (8)0.2291 (3)0.2636 (2)0.0488 (9)
C80.55269 (8)0.2054 (3)0.3611 (2)0.0505 (9)
C90.54903 (10)0.0538 (4)0.4003 (3)0.0685 (11)
C100.56676 (11)−0.0710 (4)0.3463 (3)0.0788 (14)
C110.58873 (11)−0.0459 (3)0.2499 (3)0.0726 (11)
C120.59331 (10)0.1022 (3)0.2086 (3)0.0606 (10)
C130.53137 (9)0.3347 (4)0.4206 (2)0.0562 (10)
H10.557400.447000.229100.0670*
H20.710400.263500.178800.0790*
H2A0.498500.365300.537600.1080*
H30.781300.265500.307600.0940*
H50.727200.597400.491500.0940*
H60.656400.595800.363800.0860*
H90.534100.036400.465500.0820*
H100.56390−0.171500.374600.0940*
H110.60060−0.130200.212200.0870*
H120.608100.117600.143000.0730*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0724 (2)0.1642 (5)0.1042 (4)−0.0277 (2)−0.0048 (2)0.0332 (3)
S10.0662 (4)0.0525 (4)0.0493 (4)0.0040 (3)0.0221 (3)0.0044 (3)
O10.0667 (12)0.0678 (13)0.0586 (12)0.0035 (10)0.0251 (10)0.0005 (10)
O20.0768 (13)0.0831 (13)0.0641 (13)−0.0003 (11)0.0362 (11)0.0049 (11)
O30.0920 (14)0.0549 (12)0.0700 (14)0.0115 (10)0.0218 (11)0.0149 (10)
O40.0860 (13)0.0710 (12)0.0478 (11)−0.0033 (10)0.0273 (10)−0.0051 (10)
N10.0548 (12)0.0553 (13)0.0600 (15)0.0105 (10)0.0206 (11)0.0067 (11)
C10.0595 (15)0.0492 (15)0.0499 (16)−0.0006 (12)0.0226 (13)0.0021 (13)
C20.0743 (19)0.0599 (18)0.066 (2)0.0077 (15)0.0182 (16)−0.0043 (15)
C30.069 (2)0.084 (2)0.086 (3)0.0129 (17)0.0198 (19)0.006 (2)
C40.0598 (17)0.089 (2)0.064 (2)−0.0170 (17)0.0137 (15)0.0162 (18)
C50.076 (2)0.100 (3)0.061 (2)−0.0116 (19)0.0177 (18)−0.0176 (18)
C60.074 (2)0.079 (2)0.065 (2)0.0075 (16)0.0227 (17)−0.0166 (17)
C70.0403 (13)0.0554 (16)0.0510 (16)−0.0008 (11)0.0079 (12)−0.0010 (13)
C80.0388 (12)0.0612 (17)0.0529 (16)−0.0032 (12)0.0112 (11)0.0012 (14)
C90.0602 (17)0.073 (2)0.077 (2)−0.0094 (15)0.0259 (16)0.0083 (18)
C100.074 (2)0.0595 (19)0.106 (3)−0.0088 (16)0.024 (2)0.0123 (19)
C110.076 (2)0.0557 (19)0.090 (2)−0.0043 (15)0.0251 (18)−0.0065 (17)
C120.0607 (17)0.0576 (18)0.0665 (19)−0.0056 (13)0.0196 (14)−0.0032 (15)
C130.0402 (13)0.080 (2)0.0490 (16)−0.0046 (13)0.0080 (12)0.0015 (15)

Geometric parameters (Å, °)

Br1—C41.882 (3)C7—C121.382 (4)
S1—O31.4184 (19)C7—C81.404 (3)
S1—O41.4186 (19)C8—C131.476 (4)
S1—N11.625 (2)C8—C91.386 (4)
S1—C11.758 (3)C9—C101.368 (5)
O1—C131.225 (4)C10—C111.371 (5)
O2—C131.317 (3)C11—C121.370 (4)
O2—H2A0.8200C2—H20.9300
N1—C71.418 (3)C3—H30.9300
N1—H10.8600C5—H50.9300
C1—C61.371 (4)C6—H60.9300
C1—C21.379 (4)C9—H90.9300
C2—C31.371 (5)C10—H100.9300
C3—C41.363 (5)C11—H110.9300
C4—C51.374 (5)C12—H120.9300
C5—C61.364 (5)
Br1···C9i3.662 (3)C12···O42.987 (3)
Br1···C10i3.540 (3)C13···N1vi3.325 (3)
Br1···C11i3.599 (3)C13···O3iii3.182 (3)
S1···H122.8600C13···C7vi3.543 (3)
O1···N12.670 (3)C2···H5v3.0500
O1···O2ii2.703 (3)C5···H2ix3.0900
O2···O3iii3.205 (3)C6···H3ix3.0200
O2···O1ii2.703 (3)C9···H9vii3.0700
O3···C11iv3.369 (3)C13···H12.6300
O3···C13v3.182 (3)C13···H1vi2.9700
O3···O2v3.205 (3)C13···H2Aii2.7700
O4···C6v3.185 (4)H1···O12.1300
O4···C5v3.384 (4)H1···C132.6300
O4···C122.987 (3)H1···O1vi2.7100
O1···H12.1300H1···C13vi2.9700
O1···H2Aii1.8900H2···O42.5500
O1···H1vi2.7100H2···H5v2.5900
O2···H92.3500H2···C5x3.0900
O2···H10vii2.8000H2A···O1ii1.8900
O3···H11iv2.4700H2A···C13ii2.7700
O3···H62.7600H2A···H2Aii2.4700
O4···H122.3100H3···C6x3.0200
O4···H22.5500H5···C2iii3.0500
O4···H6v2.5600H5···H2iii2.5900
N1···O12.670 (3)H6···O32.7600
N1···C13vi3.325 (3)H6···O4iii2.5600
C5···O4iii3.384 (4)H9···O22.3500
C6···O4iii3.185 (4)H9···C9vii3.0700
C7···C13vi3.543 (3)H9···H9vii2.2500
C9···Br1i3.661 (3)H10···O2vii2.8000
C10···Br1i3.540 (3)H11···O3viii2.4700
C11···Br1i3.599 (3)H12···S12.8600
C11···O3viii3.369 (3)H12···O42.3100
O3—S1—O4120.06 (12)C9—C8—C13119.7 (2)
O3—S1—N1104.36 (12)C8—C9—C10122.2 (3)
O3—S1—C1108.04 (13)C9—C10—C11119.2 (3)
O4—S1—N1109.57 (11)C10—C11—C12120.6 (3)
O4—S1—C1107.82 (12)C7—C12—C11120.7 (3)
N1—S1—C1106.21 (11)O1—C13—O2121.8 (3)
C13—O2—H2A109.00O1—C13—C8124.5 (2)
S1—N1—C7125.76 (16)O2—C13—C8113.7 (3)
C7—N1—H1117.00C1—C2—H2120.00
S1—N1—H1117.00C3—C2—H2120.00
S1—C1—C2121.2 (2)C2—C3—H3120.00
S1—C1—C6118.6 (2)C4—C3—H3120.00
C2—C1—C6120.2 (3)C4—C5—H5120.00
C1—C2—C3119.5 (3)C6—C5—H5120.00
C2—C3—C4120.0 (3)C1—C6—H6120.00
Br1—C4—C3120.5 (2)C5—C6—H6120.00
Br1—C4—C5118.9 (3)C8—C9—H9119.00
C3—C4—C5120.6 (3)C10—C9—H9119.00
C4—C5—C6119.7 (3)C9—C10—H10120.00
C1—C6—C5120.0 (3)C11—C10—H10120.00
C8—C7—C12119.6 (2)C10—C11—H11120.00
N1—C7—C12120.9 (2)C12—C11—H11120.00
N1—C7—C8119.5 (2)C7—C12—H12120.00
C7—C8—C9117.9 (2)C11—C12—H12120.00
C7—C8—C13122.5 (2)
O3—S1—N1—C7−176.5 (2)Br1—C4—C5—C6177.9 (3)
O4—S1—N1—C753.8 (2)C3—C4—C5—C60.0 (5)
C1—S1—N1—C7−62.4 (2)C4—C5—C6—C1−1.3 (5)
O3—S1—C1—C2−135.0 (2)N1—C7—C8—C9179.5 (2)
O4—S1—C1—C2−3.8 (3)N1—C7—C8—C130.7 (3)
N1—S1—C1—C2113.6 (2)C12—C7—C8—C91.8 (4)
O3—S1—C1—C643.2 (3)C12—C7—C8—C13−177.0 (2)
O4—S1—C1—C6174.3 (2)N1—C7—C12—C11−179.2 (3)
N1—S1—C1—C6−68.3 (3)C8—C7—C12—C11−1.6 (4)
S1—N1—C7—C8149.12 (19)C7—C8—C9—C10−0.9 (4)
S1—N1—C7—C12−33.3 (3)C13—C8—C9—C10177.9 (3)
S1—C1—C6—C5−175.6 (3)C7—C8—C13—O1−1.4 (4)
S1—C1—C2—C3175.7 (2)C7—C8—C13—O2176.9 (2)
C6—C1—C2—C3−2.4 (4)C9—C8—C13—O1179.9 (3)
C2—C1—C6—C52.5 (5)C9—C8—C13—O2−1.9 (3)
C1—C2—C3—C41.1 (5)C8—C9—C10—C11−0.3 (5)
C2—C3—C4—C50.1 (5)C9—C10—C11—C120.6 (5)
C2—C3—C4—Br1−177.7 (2)C10—C11—C12—C70.3 (5)

Symmetry codes: (i) −x+3/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1, z+1/2; (iv) x, y+1, z; (v) x, −y+1, z−1/2; (vi) −x+1, y, −z+1/2; (vii) −x+1, −y, −z+1; (viii) x, y−1, z; (ix) −x+3/2, y+1/2, −z+1/2; (x) −x+3/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.132.670 (3)121
O2—H2A···O1ii0.821.892.703 (3)173
C6—H6···O4iii0.932.563.185 (4)125
C11—H11···O3viii0.932.473.369 (3)164
C12—H12···O40.932.312.987 (3)130

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2431).

References

  • Allison, B. D., Phuong, V. K., McAtee, L. C., Rosen, M., Magda Morton, M., Prendergast, C., Barrett, T., Lagaud, G., Jamie Freedman, J., Lina Li, L., Xiaodong Wu, X., Venkatesan, H., Pippel, M., Woods, C., Rizzolio, M. C., Hack, M., Hoey, K., Deng, X., King, C., Shankley, N. P. & Rabinowitz, M. H. (2006). J. Med. Chem.49, 6371–6390. [PubMed]
  • Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst.32, 339–340.
  • Arshad, M. N., Khan, I. U., Shafiq, M. & Mukhtar, A. (2009). Acta Cryst. E65, o549. [PMC free article] [PubMed]
  • Asiri, A. M., Akkurt, M., Khan, S. A., Arshad, M. N., Khan, I. U. & Sharif, H. M. A. (2009). Acta Cryst. E65, o1246–o1247. [PMC free article] [PubMed]
  • 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.
  • Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst.28, 53–56.
  • Shafiq, M., Tahir, M. N., Khan, I. U., Arshad, M. N. & Asghar, M. N. (2009). Acta Cryst. E65, o1182. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • 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. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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