2-benzenesulfonamidobenzoic Acid.

In the title compound, C(13)H(11)NO(4)S, the dihedral angle between the planes of the benzene ring and the carboxyl group is 13.7 (1)°. The mol-ecular structure contains intra-molecular N-H⋯O and C-H⋯O hydrogen-bonding inter-actions, while the crystal packing is stabilized by C-H⋯O and O-H⋯O hydrogen bonds and C-H⋯π inter-actions. The O-H⋯O hydrogen bonds form a cyclic dimer, with graph-set motif R(2) (2)(8), about a centre of symmetry.

Related literature

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-length data, see: Allen et al. (1987 ▶). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C13H11NO4S

M = 277.30

Monoclinic,

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)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶).

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

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

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

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

Bruker Kappa APEXII CCD area-detector diffractometer	1824 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.047
graphite	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 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

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.

	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*

	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)

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)

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

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) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C7–C12 ring.