3-[4-(Acetamido)-benzene-sulfonamido]-benzoic acid.

In the title compound, C(15)H(14)N(2)O(5)S, the dihedral angle between the aromatic rings is 63.20 (11) Å. The crystal structure displays classical inter-molecular O-H⋯O hydrogen bonding typical for carb-oxy-lic acids, forming centrosymmetric dimers. These dimers are further connected by N-H⋯O and C-H⋯O hydrogen bonds to form an extended network.

Related literature

For the synthesis of related compounds, see: Khan et al. (2009 ▶); Arshad et al. (2008 ▶). For the biological activity of sulfonamides, see: Esteve & Bidal (2002 ▶); Hanson et al. (1999 ▶); Lee & Lee (2002 ▶); Moree et al. (1991 ▶); Ozbek et al. (2007 ▶); Parari et al. (2008 ▶); Ratish et al. (2009 ▶); Rough et al. (1998 ▶); Selnam et al. (2001 ▶); Soledade et al. (2006 ▶); Xiao & Timberlake (2000 ▶). For related structures, see: Gowda et al. (2007a ▶,b ▶,c ▶); Haider et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N2O5S

M = 334.34

Triclinic,

a = 7.9829 (3) Å

b = 8.4143 (3) Å

c = 12.6554 (5) Å

α = 70.888 (2)°

β = 81.553 (2)°

γ = 77.104 (2)°

V = 780.44 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.24 × 0.18 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

13620 measured reflections

3835 independent reflections

2928 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.150

S = 1.02

3835 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.47 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: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048397/sj5052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048397/sj5052Isup2.hkl

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

C15H14N2O5S	Z = 2
Mr = 334.34	F(000) = 348
Triclinic, P1	Dx = 1.423 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9829 (3) Å	Cell parameters from 5086 reflections
b = 8.4143 (3) Å	θ = 2.6–27.5°
c = 12.6554 (5) Å	µ = 0.23 mm−1
α = 70.888 (2)°	T = 296 K
β = 81.553 (2)°	Needles, dark brown
γ = 77.104 (2)°	0.24 × 0.18 × 0.14 mm
V = 780.44 (5) Å3

Bruker APEXII CCD area-detector diffractometer	2928 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
graphite	θmax = 28.3°, θmin = 2.7°
φ and ω scans	h = −9→10
13620 measured reflections	k = −10→11
3835 independent reflections	l = −16→16

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0733P)2 + 0.3675P] where P = (Fo2 + 2Fc2)/3
3835 reflections	(Δ/σ)max = 0.034
210 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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	0.36529 (6)	0.60917 (7)	0.20813 (4)	0.03843 (18)
N1	0.1928 (2)	0.5659 (2)	0.28924 (14)	0.0397 (4)
H1	0.1346	0.4996	0.2775	0.048*
O2	0.50673 (18)	0.5656 (2)	0.27558 (14)	0.0503 (4)
O1	0.3732 (2)	0.5277 (2)	0.12378 (13)	0.0489 (4)
C4	0.2682 (3)	1.1815 (3)	0.03783 (17)	0.0380 (5)
C1	0.3286 (2)	0.8313 (3)	0.14368 (17)	0.0373 (4)
N3	0.2462 (2)	1.3587 (2)	−0.01344 (14)	0.0424 (4)
H3	0.2964	1.4127	0.0158	0.051*
O16	0.0723 (2)	1.3984 (2)	−0.14922 (15)	0.0601 (5)
C7	0.1369 (3)	0.6366 (3)	0.37967 (17)	0.0370 (4)
O5	−0.3233 (3)	0.9184 (3)	0.57458 (17)	0.0786 (7)
C14	0.1564 (3)	1.4568 (3)	−0.10295 (18)	0.0421 (5)
O4	−0.3591 (3)	0.9200 (4)	0.40422 (19)	0.0954 (9)
C9	−0.0886 (3)	0.7910 (3)	0.47573 (18)	0.0437 (5)
C12	0.2427 (3)	0.6086 (3)	0.46374 (19)	0.0511 (6)
H12	0.3535	0.5447	0.4610	0.061*
C8	−0.0291 (3)	0.7287 (3)	0.38531 (18)	0.0411 (5)
H8	−0.1007	0.7490	0.3288	0.049*
C10	0.0194 (3)	0.7651 (3)	0.5583 (2)	0.0530 (6)
H10	−0.0194	0.8083	0.6182	0.064*
C11	0.1851 (3)	0.6745 (4)	0.5510 (2)	0.0593 (7)
H11	0.2586	0.6580	0.6058	0.071*
C15	0.1669 (3)	1.6414 (3)	−0.1392 (2)	0.0518 (6)
H15A	0.0989	1.7018	−0.2019	0.078*
H15B	0.2847	1.6541	−0.1608	0.078*
H15C	0.1237	1.6877	−0.0784	0.078*
C6	0.2468 (5)	0.9002 (4)	0.0475 (3)	0.0854 (11)
H6	0.2102	0.8281	0.0172	0.102*
C5	0.2170 (5)	1.0723 (4)	−0.0058 (3)	0.0823 (11)
H5	0.1618	1.1157	−0.0720	0.099*
C13	−0.2682 (3)	0.8827 (4)	0.4850 (2)	0.0570 (7)
C2	0.3792 (5)	0.9385 (4)	0.1877 (2)	0.0757 (10)
H2	0.4357	0.8940	0.2533	0.091*
C3	0.3476 (5)	1.1122 (4)	0.1358 (2)	0.0760 (10)
H4	0.3807	1.1841	0.1679	0.091*
H7	−0.4296	0.9779	0.5730	0.30 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.0298 (3)	0.0460 (3)	0.0443 (3)	−0.0019 (2)	−0.0027 (2)	−0.0237 (2)
N1	0.0351 (9)	0.0448 (10)	0.0441 (10)	−0.0086 (7)	−0.0023 (7)	−0.0196 (8)
O2	0.0323 (8)	0.0616 (10)	0.0597 (10)	0.0010 (7)	−0.0102 (7)	−0.0257 (8)
O1	0.0472 (9)	0.0552 (10)	0.0543 (9)	−0.0056 (7)	0.0007 (7)	−0.0346 (8)
C4	0.0325 (10)	0.0502 (12)	0.0366 (10)	−0.0100 (9)	−0.0007 (8)	−0.0199 (9)
C1	0.0319 (9)	0.0462 (12)	0.0393 (11)	−0.0091 (8)	0.0007 (8)	−0.0208 (9)
N3	0.0442 (10)	0.0486 (11)	0.0414 (10)	−0.0124 (8)	−0.0087 (8)	−0.0185 (8)
O16	0.0570 (10)	0.0703 (12)	0.0606 (11)	−0.0117 (9)	−0.0257 (8)	−0.0210 (9)
C7	0.0352 (10)	0.0405 (11)	0.0341 (10)	−0.0052 (8)	−0.0019 (8)	−0.0112 (9)
O5	0.0565 (11)	0.1177 (18)	0.0653 (12)	0.0201 (11)	−0.0089 (9)	−0.0554 (12)
C14	0.0339 (10)	0.0570 (13)	0.0385 (11)	−0.0055 (9)	0.0001 (8)	−0.0221 (10)
O4	0.0579 (12)	0.156 (2)	0.0790 (14)	0.0398 (13)	−0.0287 (11)	−0.0740 (15)
C9	0.0404 (11)	0.0497 (13)	0.0409 (12)	−0.0025 (9)	−0.0047 (9)	−0.0169 (10)
C12	0.0372 (11)	0.0699 (16)	0.0423 (12)	0.0038 (11)	−0.0099 (9)	−0.0182 (11)
C8	0.0372 (10)	0.0485 (12)	0.0376 (11)	−0.0019 (9)	−0.0089 (8)	−0.0146 (9)
C10	0.0522 (13)	0.0692 (16)	0.0402 (12)	−0.0033 (12)	−0.0059 (10)	−0.0244 (12)
C11	0.0489 (13)	0.089 (2)	0.0423 (13)	−0.0005 (13)	−0.0159 (10)	−0.0255 (13)
C15	0.0544 (14)	0.0541 (14)	0.0452 (13)	−0.0014 (11)	−0.0027 (10)	−0.0190 (11)
C6	0.130 (3)	0.0517 (16)	0.096 (2)	−0.0114 (17)	−0.075 (2)	−0.0271 (15)
C5	0.129 (3)	0.0534 (16)	0.080 (2)	−0.0076 (17)	−0.071 (2)	−0.0206 (14)
C13	0.0486 (13)	0.0706 (17)	0.0553 (15)	0.0080 (12)	−0.0088 (11)	−0.0347 (13)
C2	0.128 (3)	0.0570 (16)	0.0561 (16)	−0.0268 (17)	−0.0497 (17)	−0.0113 (13)
C3	0.129 (3)	0.0529 (15)	0.0634 (17)	−0.0294 (17)	−0.0507 (18)	−0.0142 (13)

S1—O2	1.4252 (15)	O4—C13	1.255 (3)
S1—O1	1.4331 (15)	C9—C10	1.383 (3)
S1—N1	1.6264 (17)	C9—C8	1.390 (3)
S1—C1	1.753 (2)	C9—C13	1.477 (3)
N1—C7	1.428 (2)	C12—C11	1.369 (3)
N1—H1	0.8600	C12—H12	0.9300
C4—C3	1.368 (3)	C8—H8	0.9300
C4—C5	1.372 (3)	C10—C11	1.378 (4)
C4—N3	1.399 (3)	C10—H10	0.9300
C1—C2	1.359 (3)	C11—H11	0.9300
C1—C6	1.359 (3)	C15—H15A	0.9600
N3—C14	1.357 (3)	C15—H15B	0.9600
N3—H3	0.8600	C15—H15C	0.9600
O16—C14	1.219 (3)	C6—C5	1.365 (4)
C7—C8	1.383 (3)	C6—H6	0.9300
C7—C12	1.383 (3)	C5—H5	0.9300
O5—C13	1.260 (3)	C2—C3	1.374 (4)
O5—H7	0.8831	C2—H2	0.9300
C14—C15	1.487 (3)	C3—H4	0.9300
O2—S1—O1	119.27 (9)	C7—C8—C9	119.82 (19)
O2—S1—N1	108.91 (9)	C7—C8—H8	120.1
O1—S1—N1	105.07 (9)	C9—C8—H8	120.1
O2—S1—C1	107.95 (10)	C11—C10—C9	119.4 (2)
O1—S1—C1	108.32 (10)	C11—C10—H10	120.3
N1—S1—C1	106.68 (9)	C9—C10—H10	120.3
C7—N1—S1	120.87 (14)	C12—C11—C10	120.6 (2)
C7—N1—H1	119.6	C12—C11—H11	119.7
S1—N1—H1	119.6	C10—C11—H11	119.7
C3—C4—C5	117.9 (2)	C14—C15—H15A	109.5
C3—C4—N3	118.54 (19)	C14—C15—H15B	109.5
C5—C4—N3	123.5 (2)	H15A—C15—H15B	109.5
C2—C1—C6	118.4 (2)	C14—C15—H15C	109.5
C2—C1—S1	121.67 (18)	H15A—C15—H15C	109.5
C6—C1—S1	119.95 (17)	H15B—C15—H15C	109.5
C14—N3—C4	128.83 (18)	C1—C6—C5	121.8 (2)
C14—N3—H3	115.6	C1—C6—H6	119.1
C4—N3—H3	115.6	C5—C6—H6	119.1
C8—C7—C12	119.55 (19)	C6—C5—C4	120.2 (2)
C8—C7—N1	119.05 (18)	C6—C5—H5	119.9
C12—C7—N1	121.34 (19)	C4—C5—H5	119.9
C13—O5—H7	113.2	O4—C13—O5	123.1 (2)
O16—C14—N3	122.6 (2)	O4—C13—C9	118.9 (2)
O16—C14—C15	122.7 (2)	O5—C13—C9	118.0 (2)
N3—C14—C15	114.73 (19)	C1—C2—C3	120.4 (2)
C10—C9—C8	120.1 (2)	C1—C2—H2	119.8
C10—C9—C13	119.8 (2)	C3—C2—H2	119.8
C8—C9—C13	120.1 (2)	C4—C3—C2	121.2 (2)
C11—C12—C7	120.4 (2)	C4—C3—H4	119.4
C11—C12—H12	119.8	C2—C3—H4	119.4
C7—C12—H12	119.8
O2—S1—N1—C7	55.28 (18)	C13—C9—C8—C7	−177.2 (2)
O1—S1—N1—C7	−175.87 (15)	C8—C9—C10—C11	−1.1 (4)
C1—S1—N1—C7	−60.99 (17)	C13—C9—C10—C11	177.9 (3)
O2—S1—C1—C2	−23.6 (3)	C7—C12—C11—C10	2.0 (4)
O1—S1—C1—C2	−154.0 (2)	C9—C10—C11—C12	−0.8 (4)
N1—S1—C1—C2	93.4 (2)	C2—C1—C6—C5	0.8 (5)
O2—S1—C1—C6	156.7 (2)	S1—C1—C6—C5	−179.4 (3)
O1—S1—C1—C6	26.3 (3)	C1—C6—C5—C4	−0.7 (6)
N1—S1—C1—C6	−86.4 (3)	C3—C4—C5—C6	−0.6 (5)
C3—C4—N3—C14	−172.3 (3)	N3—C4—C5—C6	178.3 (3)
C5—C4—N3—C14	8.9 (4)	C10—C9—C13—O4	173.0 (3)
S1—N1—C7—C8	124.75 (19)	C8—C9—C13—O4	−8.0 (4)
S1—N1—C7—C12	−57.9 (3)	C10—C9—C13—O5	−7.6 (4)
C4—N3—C14—O16	3.6 (3)	C8—C9—C13—O5	171.4 (3)
C4—N3—C14—C15	−177.18 (19)	C6—C1—C2—C3	0.2 (5)
C8—C7—C12—C11	−1.3 (4)	S1—C1—C2—C3	−179.5 (3)
N1—C7—C12—C11	−178.6 (2)	C5—C4—C3—C2	1.6 (5)
C12—C7—C8—C9	−0.6 (3)	N3—C4—C3—C2	−177.3 (3)
N1—C7—C8—C9	176.8 (2)	C1—C2—C3—C4	−1.5 (5)
C10—C9—C8—C7	1.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H7···O4i	0.88	1.74	2.617 (4)	170
N1—H1···O16ii	0.86	2.31	2.860 (2)	122
N3—H3···O1iii	0.86	2.13	2.974 (2)	165
C11—H11···O2iv	0.93	2.59	3.379 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H7⋯O4i	0.88	1.74	2.617 (4)	170
N1—H1⋯O16ii	0.86	2.31	2.860 (2)	122
N3—H3⋯O1iii	0.86	2.13	2.974 (2)	165
C11—H11⋯O2iv	0.93	2.59	3.379 (3)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .