4-{[(4-Methyl-phen-yl)sulfon-yl]amino}-benzoic acid.

In the title compound, C(14)H(13)NO(4)S, the dihedral angle between the aromatic rings is 35.47 (10)°. In the crystal, adjacent mol-ecules are connected by pairs of O-H⋯O hydrogen bonds, forming head-to-head centrosymmetric dimers typical for carb-oxy-lic acids. Adjacent dimers are further linked through C-H⋯O inter-actions on one side and N-H⋯O inter-actions on the other, generating [010] chains.

Related literature

For background to the biological activity of sulfonamides, see: Hanson et al. (1999 ▶). For related structures, see: Gowda et al. (2007 ▶); Arshad et al. (2008 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C14H13NO4S

M = 291.31

Triclinic,

a = 5.1588 (2) Å

b = 6.9277 (2) Å

c = 20.0350 (6) Å

α = 83.574 (1)°

β = 86.357 (1)°

γ = 72.824 (1)°

V = 679.44 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.35 × 0.31 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

12209 measured reflections

3313 independent reflections

2660 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.147

S = 1.01

3310 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.22 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global, New_Global_Publ_Block. DOI: 10.1107/S1600536811011524/hb5824sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011524/hb5824Isup2.hkl

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

C14H13NO4S	Z = 2
Mr = 291.31	F(000) = 304
Triclinic, P1	Dx = 1.424 Mg m−3
Hall symbol: -P 1	Melting point: 503 K
a = 5.1588 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.9277 (2) Å	Cell parameters from 5143 reflections
c = 20.0350 (6) Å	θ = 3.1–27.8°
α = 83.574 (1)°	µ = 0.25 mm−1
β = 86.357 (1)°	T = 296 K
γ = 72.824 (1)°	Needles, colourless
V = 679.44 (4) Å3	0.35 × 0.31 × 0.22 mm

Bruker APEXII CCD diffractometer	2660 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 28.3°, θmin = 1.0°
φ and ω scans	h = −6→6
12209 measured reflections	k = −9→9
3313 independent reflections	l = −26→26

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0982P)2 + 0.0842P] where P = (Fo2 + 2Fc2)/3
3310 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.22 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 > 2σ(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
C1	1.0578 (3)	−0.2205 (2)	0.33980 (8)	0.0363 (3)
C2	0.8392 (3)	−0.0474 (3)	0.33116 (9)	0.0450 (4)
H2	0.7040	−0.0414	0.3017	0.054*
C3	0.8230 (3)	0.1167 (3)	0.36655 (9)	0.0447 (4)
H3	0.6746	0.2320	0.3617	0.054*
C4	1.0281 (3)	0.1089 (2)	0.40922 (8)	0.0357 (3)
C5	1.2453 (3)	−0.0655 (3)	0.41777 (8)	0.0406 (4)
H5	1.3824	−0.0711	0.4465	0.049*
C6	1.2585 (3)	−0.2306 (3)	0.38368 (9)	0.0415 (4)
H6	1.4022	−0.3485	0.3902	0.050*
C7	1.0157 (3)	0.2840 (2)	0.44689 (8)	0.0381 (4)
C8	1.1343 (4)	−0.2279 (3)	0.17695 (9)	0.0435 (4)
C9	0.9505 (5)	−0.2551 (3)	0.13444 (11)	0.0634 (6)
H9	0.9213	−0.3814	0.1345	0.076*
C10	0.8108 (6)	−0.0924 (4)	0.09195 (13)	0.0786 (7)
H10	0.6877	−0.1112	0.0631	0.094*
C11	0.8470 (5)	0.0958 (4)	0.09073 (12)	0.0670 (6)
C12	1.0313 (6)	0.1180 (4)	0.13297 (14)	0.0757 (7)
H12	1.0603	0.2444	0.1326	0.091*
C13	1.1759 (5)	−0.0405 (3)	0.17613 (12)	0.0652 (6)
H13	1.3002	−0.0211	0.2044	0.078*
C14	0.6831 (8)	0.2757 (5)	0.04587 (16)	0.1065 (11)
H14A	0.6420	0.2297	0.0055	0.160*
H14B	0.7864	0.3703	0.0347	0.160*
H14C	0.5172	0.3411	0.0691	0.160*
N1	1.0818 (3)	−0.3933 (2)	0.30382 (7)	0.0424 (3)
O1	1.5356 (2)	−0.3963 (2)	0.25576 (7)	0.0559 (4)
O2	1.2874 (3)	−0.6138 (2)	0.21531 (8)	0.0617 (4)
O3	1.2221 (3)	0.2721 (2)	0.47994 (7)	0.0549 (4)
H3O	1.1959	0.3755	0.4989	0.082*
O4	0.8069 (3)	0.43283 (18)	0.44517 (7)	0.0507 (3)
S1	1.28689 (8)	−0.42565 (6)	0.23758 (2)	0.04325 (17)
H1N	0.937 (4)	−0.412 (3)	0.2967 (10)	0.052*

	U11	U22	U33	U12	U13	U23
C1	0.0353 (8)	0.0366 (8)	0.0385 (8)	−0.0115 (6)	−0.0060 (6)	−0.0040 (6)
C2	0.0334 (8)	0.0505 (10)	0.0511 (10)	−0.0074 (7)	−0.0150 (7)	−0.0102 (8)
C3	0.0359 (8)	0.0417 (9)	0.0527 (10)	−0.0019 (7)	−0.0148 (7)	−0.0066 (7)
C4	0.0349 (8)	0.0357 (8)	0.0363 (8)	−0.0092 (6)	−0.0071 (6)	−0.0023 (6)
C5	0.0350 (8)	0.0420 (9)	0.0434 (9)	−0.0058 (7)	−0.0146 (6)	−0.0063 (7)
C6	0.0374 (8)	0.0368 (8)	0.0459 (9)	−0.0015 (7)	−0.0125 (7)	−0.0052 (7)
C7	0.0373 (8)	0.0374 (8)	0.0392 (8)	−0.0092 (6)	−0.0081 (6)	−0.0022 (6)
C8	0.0424 (9)	0.0475 (10)	0.0422 (9)	−0.0129 (7)	−0.0053 (7)	−0.0104 (7)
C9	0.0781 (14)	0.0604 (13)	0.0591 (12)	−0.0270 (11)	−0.0262 (11)	−0.0055 (10)
C10	0.0892 (17)	0.0836 (17)	0.0660 (14)	−0.0247 (14)	−0.0404 (13)	0.0000 (12)
C11	0.0753 (15)	0.0612 (13)	0.0551 (12)	−0.0048 (11)	−0.0143 (11)	−0.0003 (10)
C12	0.1027 (19)	0.0499 (13)	0.0779 (16)	−0.0253 (12)	−0.0269 (14)	0.0012 (11)
C13	0.0770 (15)	0.0537 (12)	0.0718 (14)	−0.0258 (11)	−0.0268 (11)	−0.0027 (10)
C14	0.124 (3)	0.089 (2)	0.088 (2)	−0.0063 (18)	−0.037 (2)	0.0206 (16)
N1	0.0406 (8)	0.0443 (8)	0.0478 (8)	−0.0178 (6)	−0.0080 (6)	−0.0087 (6)
O1	0.0349 (7)	0.0683 (9)	0.0644 (8)	−0.0120 (6)	−0.0093 (6)	−0.0104 (7)
O2	0.0688 (9)	0.0442 (8)	0.0713 (9)	−0.0070 (7)	−0.0126 (7)	−0.0218 (7)
O3	0.0473 (7)	0.0476 (8)	0.0707 (9)	−0.0054 (6)	−0.0238 (6)	−0.0202 (6)
O4	0.0473 (7)	0.0399 (7)	0.0603 (8)	0.0001 (5)	−0.0193 (6)	−0.0110 (6)
S1	0.0381 (3)	0.0422 (3)	0.0497 (3)	−0.00771 (18)	−0.00885 (18)	−0.01246 (18)

C1—C6	1.382 (2)	C9—C10	1.378 (3)
C1—C2	1.386 (2)	C9—H9	0.9300
C1—N1	1.436 (2)	C10—C11	1.368 (3)
C2—C3	1.385 (2)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.364 (3)
C3—C4	1.387 (2)	C11—C14	1.517 (3)
C3—H3	0.9300	C12—C13	1.377 (3)
C4—C5	1.387 (2)	C12—H12	0.9300
C4—C7	1.482 (2)	C13—H13	0.9300
C5—C6	1.379 (2)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O4	1.251 (2)	N1—S1	1.6366 (16)
C7—O3	1.2670 (19)	N1—H1N	0.82 (2)
C8—C13	1.375 (3)	O1—S1	1.4321 (13)
C8—C9	1.380 (2)	O2—S1	1.4232 (13)
C8—S1	1.7564 (19)	O3—H3O	0.8200
C6—C1—C2	120.40 (15)	C11—C10—H10	118.9
C6—C1—N1	118.37 (14)	C9—C10—H10	118.9
C2—C1—N1	121.23 (14)	C12—C11—C10	117.6 (2)
C3—C2—C1	119.66 (15)	C12—C11—C14	120.8 (2)
C3—C2—H2	120.2	C10—C11—C14	121.7 (2)
C1—C2—H2	120.2	C11—C12—C13	122.2 (2)
C2—C3—C4	120.00 (15)	C11—C12—H12	118.9
C2—C3—H3	120.0	C13—C12—H12	118.9
C4—C3—H3	120.0	C8—C13—C12	119.23 (19)
C5—C4—C3	119.86 (14)	C8—C13—H13	120.4
C5—C4—C7	119.40 (14)	C12—C13—H13	120.4
C3—C4—C7	120.73 (14)	C11—C14—H14A	109.5
C6—C5—C4	120.15 (14)	C11—C14—H14B	109.5
C6—C5—H5	119.9	H14A—C14—H14B	109.5
C4—C5—H5	119.9	C11—C14—H14C	109.5
C5—C6—C1	119.89 (15)	H14A—C14—H14C	109.5
C5—C6—H6	120.1	H14B—C14—H14C	109.5
C1—C6—H6	120.1	C1—N1—S1	118.23 (11)
O4—C7—O3	123.49 (15)	C1—N1—H1N	114.4 (15)
O4—C7—C4	119.73 (14)	S1—N1—H1N	111.3 (15)
O3—C7—C4	116.78 (14)	C7—O3—H3O	109.5
C13—C8—C9	119.84 (19)	O2—S1—O1	119.96 (9)
C13—C8—S1	120.34 (14)	O2—S1—N1	106.32 (8)
C9—C8—S1	119.49 (15)	O1—S1—N1	106.96 (8)
C10—C9—C8	119.0 (2)	O2—S1—C8	108.93 (8)
C10—C9—H9	120.5	O1—S1—C8	108.33 (9)
C8—C9—H9	120.5	N1—S1—C8	105.41 (8)
C11—C10—C9	122.2 (2)
C6—C1—C2—C3	0.3 (3)	C9—C10—C11—C14	−177.3 (3)
N1—C1—C2—C3	−179.80 (15)	C10—C11—C12—C13	−0.7 (4)
C1—C2—C3—C4	1.5 (3)	C14—C11—C12—C13	177.5 (3)
C2—C3—C4—C5	−1.8 (3)	C9—C8—C13—C12	0.4 (3)
C2—C3—C4—C7	179.29 (16)	S1—C8—C13—C12	−173.0 (2)
C3—C4—C5—C6	0.4 (3)	C11—C12—C13—C8	0.1 (4)
C7—C4—C5—C6	179.27 (15)	C6—C1—N1—S1	−79.40 (18)
C4—C5—C6—C1	1.4 (3)	C2—C1—N1—S1	100.69 (17)
C2—C1—C6—C5	−1.7 (3)	C1—N1—S1—O2	175.57 (12)
N1—C1—C6—C5	178.34 (15)	C1—N1—S1—O1	46.27 (15)
C5—C4—C7—O4	−172.22 (16)	C1—N1—S1—C8	−68.88 (13)
C3—C4—C7—O4	6.7 (3)	C13—C8—S1—O2	−161.30 (17)
C5—C4—C7—O3	7.4 (2)	C9—C8—S1—O2	25.26 (19)
C3—C4—C7—O3	−173.74 (16)	C13—C8—S1—O1	−29.26 (19)
C13—C8—C9—C10	−0.2 (3)	C9—C8—S1—O1	157.30 (17)
S1—C8—C9—C10	173.2 (2)	C13—C8—S1—N1	84.95 (18)
C8—C9—C10—C11	−0.4 (4)	C9—C8—S1—N1	−88.49 (18)
C9—C10—C11—C12	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.81 (3)	2.25 (3)	3.042 (2)	164.2 (2)
O3—H3O···O4ii	0.82	1.83	2.633 (2)	166
C5—H5···O3iii	0.93	2.55	3.397 (2)	151
C6—H6···O4iv	0.93	2.43	3.294 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.81 (3)	2.25 (3)	3.042 (2)	164.2 (2)
O3—H3O⋯O4ii	0.82	1.83	2.633 (2)	166
C5—H5⋯O3iii	0.93	2.55	3.397 (2)	151
C6—H6⋯O4iv	0.93	2.43	3.294 (3)	155

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