4-Benzene-sulfonamido-benzoic acid.

In the mol-ecule of the title sulfonamide compound, C(13)H(11)NO(4)S, 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 mol-ecules are linked via classical inter-molecular 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

C13H11NO4S

M = 277.30

Monoclinic,

a = 5.2050 (3) Å

b = 37.726 (2) Å

c = 7.3781 (4) Å

β = 117.510 (3)°

V = 1284.98 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 295 K

0.26 × 0.21 × 0.19 mm

Data collection

Bruker CCD diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.935, T max = 0.958

13550 measured reflections

3185 independent reflections

2633 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.199

S = 1.10

3185 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047291/rk2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047291/rk2179Isup2.hkl

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

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	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

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) ; (iv) .