organic compounds
4-Benzenesulfonamidobenzoic acid
aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and bCollege of Chemical Engineering and Biotechnology, Hebei Polytechnic University, Tangshan 063009, People's Republic of China
*Correspondence e-mail: iukhangcu@126.com
In the molecule of the title sulfonamide compound, C13H11NO4S, the dihedral angle between the planes of the benzene ring and the carboxyl substituent group is 6.7 (4)°. The two aromatic rings are inclined at 45.36 (15)° to one another. In the crystal, adjacent molecules are linked via classical intermolecular N—H⋯O and O—H⋯O, and non-classical C—H⋯O hydrogen bonds, which stabilize the crystal structure.
Related literature
For the biological activity and pharmaceutical applications of sulfonamide derivatives, see: Innocenti et al. (2004); Parai et al. (2008); Rathish et al. (2009); Selvam et al. (2001). For related structures of sulfonamide derivatives with 4–aminobenzoic acid, see: Arshad et al. (2009); Khan et al. (2009); Nan & Xing (2006).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809047291/rk2179sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047291/rk2179Isup2.hkl
The 4–amino benzoic acid (1 g, 7.3 mmol) was dissolved in distilled water (10 ml). The pH of the solution was adjusted at 8–9 using 1M Na2CO3. Benzene sulfonylchloride (1.29 g, 7.3 mmol) was added to the above solution and stirred at room temperature until all the suspended benzene sulfonyl chloride was consumed. On completion of the reaction the pH was adjusted 1–2, using 1N HCl acid. The precipitate obtained was filtered, washed with distilled water, dried and recrystalized in methanol to yield colourless crystals.
All H atoms were positioned geometrically an refined using a riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic, O—H = 0.82Å and Uiso(H) = 1.5Ueq(O) for the OH group and N—H = 0.81Å and Uiso(H) = 1.2Ueq(N) for the NH group.
Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C13H11NO4S | F(000) = 576 |
Mr = 277.30 | Dx = 1.433 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5008 reflections |
a = 5.2050 (3) Å | θ = 3.0–25° |
b = 37.726 (2) Å | µ = 0.26 mm−1 |
c = 7.3781 (4) Å | T = 295 K |
β = 117.510 (3)° | Block, colourless |
V = 1284.98 (13) Å3 | 0.26 × 0.21 × 0.19 mm |
Z = 4 |
Bruker CCD diffractometer | 3185 independent reflections |
Radiation source: fine–focus sealed tube | 2633 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ and ω scans | θmax = 28.4°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −4→6 |
Tmin = 0.935, Tmax = 0.958 | k = −50→45 |
13550 measured reflections | l = −9→9 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0878P)2 + 1.4857P] where P = (Fo2 + 2Fc2)/3 |
3185 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C13H11NO4S | V = 1284.98 (13) Å3 |
Mr = 277.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.2050 (3) Å | µ = 0.26 mm−1 |
b = 37.726 (2) Å | T = 295 K |
c = 7.3781 (4) Å | 0.26 × 0.21 × 0.19 mm |
β = 117.510 (3)° |
Bruker CCD diffractometer | 3185 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2633 reflections with I > 2σ(I) |
Tmin = 0.935, Tmax = 0.958 | Rint = 0.025 |
13550 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.38 e Å−3 |
3185 reflections | Δρmin = −0.36 e Å−3 |
172 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
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 | ||
S1 | 0.27263 (17) | 0.36345 (2) | 0.53929 (12) | 0.0443 (3) | |
O5 | −0.4876 (5) | 0.48980 (7) | −0.2675 (3) | 0.0496 (6) | |
H5 | −0.5699 | 0.5003 | −0.3768 | 0.074* | |
O6 | −0.2171 (5) | 0.47077 (6) | −0.4087 (3) | 0.0464 (5) | |
O7 | 0.4834 (6) | 0.35320 (8) | 0.7386 (4) | 0.0693 (8) | |
O8 | −0.0109 (5) | 0.37334 (7) | 0.5034 (4) | 0.0557 (6) | |
N2 | 0.4098 (5) | 0.39697 (7) | 0.4738 (4) | 0.0408 (6) | |
H2 | 0.5771 | 0.3942 | 0.5010 | 0.049* | |
C14 | 0.2360 (6) | 0.41529 (7) | 0.2848 (4) | 0.0344 (6) | |
C15 | 0.2845 (6) | 0.41056 (8) | 0.1173 (5) | 0.0411 (7) | |
H15 | 0.4269 | 0.3949 | 0.1242 | 0.049* | |
C16 | 0.1192 (6) | 0.42930 (8) | −0.0615 (5) | 0.0406 (6) | |
H16 | 0.1543 | 0.4267 | −0.1735 | 0.049* | |
C17 | −0.0980 (5) | 0.45182 (7) | −0.0728 (4) | 0.0319 (5) | |
C18 | −0.1453 (6) | 0.45608 (8) | 0.0961 (4) | 0.0375 (6) | |
H18 | −0.2921 | 0.4710 | 0.0884 | 0.045* | |
C19 | 0.0239 (6) | 0.43826 (8) | 0.2754 (4) | 0.0386 (6) | |
H19 | −0.0049 | 0.4417 | 0.3895 | 0.046* | |
C20 | 0.2370 (7) | 0.32889 (8) | 0.3691 (5) | 0.0456 (7) | |
C21 | 0.4682 (10) | 0.30652 (11) | 0.4110 (8) | 0.0731 (12) | |
H21 | 0.6402 | 0.3090 | 0.5314 | 0.088* | |
C22 | 0.4401 (13) | 0.28042 (13) | 0.2715 (11) | 0.0938 (18) | |
H22 | 0.5934 | 0.2650 | 0.2995 | 0.113* | |
C23 | 0.1881 (15) | 0.27699 (14) | 0.0918 (10) | 0.0938 (17) | |
H23 | 0.1703 | 0.2594 | −0.0015 | 0.113* | |
C24 | −0.0327 (15) | 0.29943 (14) | 0.0524 (9) | 0.1009 (19) | |
H24 | −0.2033 | 0.2972 | −0.0692 | 0.121* | |
C25 | −0.0115 (10) | 0.32565 (11) | 0.1883 (7) | 0.0724 (12) | |
H25 | −0.1653 | 0.3411 | 0.1574 | 0.087* | |
C26 | −0.2763 (6) | 0.47182 (7) | −0.2629 (4) | 0.0340 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0400 (4) | 0.0527 (5) | 0.0429 (4) | 0.0102 (3) | 0.0214 (3) | 0.0115 (3) |
O5 | 0.0442 (12) | 0.0658 (15) | 0.0422 (11) | 0.0254 (11) | 0.0228 (10) | 0.0118 (10) |
O6 | 0.0505 (12) | 0.0567 (13) | 0.0380 (11) | 0.0155 (10) | 0.0255 (10) | 0.0054 (9) |
O7 | 0.0665 (17) | 0.087 (2) | 0.0466 (14) | 0.0161 (15) | 0.0193 (13) | 0.0233 (13) |
O8 | 0.0467 (13) | 0.0653 (15) | 0.0681 (16) | 0.0086 (11) | 0.0376 (12) | 0.0058 (12) |
N2 | 0.0281 (11) | 0.0490 (14) | 0.0410 (13) | 0.0053 (10) | 0.0121 (10) | 0.0076 (10) |
C14 | 0.0279 (12) | 0.0365 (14) | 0.0357 (13) | 0.0003 (10) | 0.0122 (10) | 0.0004 (10) |
C15 | 0.0350 (14) | 0.0452 (16) | 0.0460 (15) | 0.0146 (12) | 0.0210 (12) | 0.0041 (12) |
C16 | 0.0410 (15) | 0.0483 (16) | 0.0395 (14) | 0.0095 (12) | 0.0247 (12) | 0.0008 (12) |
C17 | 0.0277 (12) | 0.0343 (13) | 0.0342 (13) | 0.0010 (10) | 0.0146 (10) | −0.0026 (10) |
C18 | 0.0361 (14) | 0.0393 (14) | 0.0421 (14) | 0.0095 (11) | 0.0223 (12) | 0.0009 (11) |
C19 | 0.0416 (15) | 0.0437 (15) | 0.0360 (14) | 0.0073 (12) | 0.0226 (12) | −0.0003 (11) |
C20 | 0.0475 (17) | 0.0407 (15) | 0.0560 (18) | 0.0068 (13) | 0.0303 (15) | 0.0121 (13) |
C21 | 0.054 (2) | 0.058 (2) | 0.108 (4) | 0.0152 (18) | 0.038 (2) | 0.003 (2) |
C22 | 0.089 (4) | 0.059 (3) | 0.156 (6) | 0.019 (2) | 0.076 (4) | −0.001 (3) |
C23 | 0.130 (5) | 0.066 (3) | 0.101 (4) | 0.008 (3) | 0.067 (4) | −0.011 (3) |
C24 | 0.122 (5) | 0.076 (3) | 0.074 (3) | 0.019 (3) | 0.019 (3) | −0.015 (3) |
C25 | 0.074 (3) | 0.060 (2) | 0.066 (2) | 0.022 (2) | 0.017 (2) | 0.0007 (19) |
C26 | 0.0307 (13) | 0.0361 (13) | 0.0346 (13) | 0.0023 (10) | 0.0146 (10) | −0.0031 (10) |
S1—O7 | 1.423 (3) | C17—C26 | 1.482 (4) |
S1—O8 | 1.423 (2) | C18—C19 | 1.379 (4) |
S1—N2 | 1.632 (3) | C18—H18 | 0.9300 |
S1—C20 | 1.760 (4) | C19—H19 | 0.9300 |
O5—C26 | 1.279 (3) | C20—C25 | 1.368 (5) |
O5—H5 | 0.8186 | C20—C21 | 1.383 (5) |
O6—C26 | 1.249 (3) | C21—C22 | 1.383 (7) |
N2—C14 | 1.440 (3) | C21—H21 | 0.9300 |
N2—H2 | 0.8048 | C22—C23 | 1.374 (8) |
C14—C19 | 1.380 (4) | C22—H22 | 0.9300 |
C14—C15 | 1.382 (4) | C23—C24 | 1.347 (8) |
C15—C16 | 1.390 (4) | C23—H23 | 0.9300 |
C15—H15 | 0.9300 | C24—C25 | 1.376 (7) |
C16—C17 | 1.386 (4) | C24—H24 | 0.9300 |
C16—H16 | 0.9300 | C25—H25 | 0.9300 |
C17—C18 | 1.386 (4) | ||
O7—S1—O8 | 120.12 (17) | C14—C19—C18 | 119.7 (3) |
O7—S1—N2 | 106.43 (16) | C14—C19—H19 | 120.1 |
O8—S1—N2 | 107.42 (14) | C18—C19—H19 | 120.1 |
O7—S1—C20 | 108.24 (17) | C25—C20—C21 | 119.8 (4) |
O8—S1—C20 | 107.64 (16) | C25—C20—S1 | 120.2 (3) |
N2—S1—C20 | 106.21 (14) | C21—C20—S1 | 119.9 (3) |
C26—O5—H5 | 109.5 | C20—C21—C22 | 119.1 (5) |
C14—N2—S1 | 119.58 (19) | C20—C21—H21 | 120.4 |
C14—N2—H2 | 115.3 | C22—C21—H21 | 120.5 |
S1—N2—H2 | 113.4 | C23—C22—C21 | 120.7 (5) |
C19—C14—C15 | 120.5 (3) | C23—C22—H22 | 119.6 |
C19—C14—N2 | 118.7 (3) | C21—C22—H22 | 119.6 |
C15—C14—N2 | 120.7 (2) | C24—C23—C22 | 119.2 (5) |
C14—C15—C16 | 119.6 (3) | C24—C23—H23 | 120.4 |
C14—C15—H15 | 120.2 | C22—C23—H23 | 120.4 |
C16—C15—H15 | 120.2 | C23—C24—C25 | 121.4 (5) |
C17—C16—C15 | 119.9 (3) | C23—C24—H24 | 119.3 |
C17—C16—H16 | 120.0 | C25—C24—H24 | 119.3 |
C15—C16—H16 | 120.0 | C20—C25—C24 | 119.7 (4) |
C18—C17—C16 | 119.7 (3) | C20—C25—H25 | 120.1 |
C18—C17—C26 | 119.9 (2) | C24—C25—H25 | 120.1 |
C16—C17—C26 | 120.4 (2) | O6—C26—O5 | 123.0 (3) |
C19—C18—C17 | 120.4 (3) | O6—C26—C17 | 120.2 (2) |
C19—C18—H18 | 119.8 | O5—C26—C17 | 116.8 (2) |
C17—C18—H18 | 119.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O8i | 0.81 | 2.28 | 3.054 (4) | 162 |
O5—H5···O6ii | 0.82 | 1.82 | 2.625 (3) | 168 |
C18—H18···O5iii | 0.93 | 2.58 | 3.413 (4) | 150 |
C19—H19···O6iv | 0.93 | 2.48 | 3.348 (4) | 155 |
Symmetry codes: (i) x+1, y, z; (ii) −x−1, −y+1, −z−1; (iii) −x−1, −y+1, −z; (iv) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H11NO4S |
Mr | 277.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 5.2050 (3), 37.726 (2), 7.3781 (4) |
β (°) | 117.510 (3) |
V (Å3) | 1284.98 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.26 × 0.21 × 0.19 |
Data collection | |
Diffractometer | Bruker CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.935, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13550, 3185, 2633 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.199, 1.10 |
No. of reflections | 3185 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.36 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O8i | 0.81 | 2.28 | 3.054 (4) | 162 |
O5—H5···O6ii | 0.82 | 1.82 | 2.625 (3) | 168 |
C18—H18···O5iii | 0.93 | 2.58 | 3.413 (4) | 150 |
C19—H19···O6iv | 0.93 | 2.48 | 3.348 (4) | 155 |
Symmetry codes: (i) x+1, y, z; (ii) −x−1, −y+1, −z−1; (iii) −x−1, −y+1, −z; (iv) x, y, z+1. |
Acknowledgements
The authors thank Government College University and the Scientific Research Fund of Hebei Provincial Education Department (project 2006114) for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Benzene sulfonamide derivative have shown antimalarial (Parai et al., 2008), carbonic anhydrase inhibitors (Innocenti et al., 2004), antiHIV (Selvam et al., 2001) and antiinflamatory (Rathish et al., 2009) activities. In continuation of synthesis and structural studies of different benzene sulfonamide derivative (Khan et al., 2009; Arshad et al., 2009), we report here the molecular and crystal structures of title compound. The molecular structure of the title compound, I, is illustrated in Fig. 1. In I, phenyl and p–aminobenzoic acid moieties are connected through the SO2 group. The structure of I is comparable with 4–(tosylamino)benzoic acid, (Nan & Xing, 2006). The dihedral angle between the planes of the benzene ring and the carboxyl substituent group is 6.7 (4)°. The two aromatic rings (C20–C25 and C14–C19) are inclined at 45.36 (15)° to one another. The torsion angle C14—N2—S1—C20 in the central part of the molecule is 70 (1)°.
In the crystal, adjacent molecules are linked via intermolecular classical N—H···O and O—H···O and non–classical C—H···O hydrogen bonds (Tab. 1, Fig. 2), which stabilize the crystal structure.