2-methanesulfonamidobenzoic Acid.

In the title compound, C(8)H(9)NO(4)S, an intra-molecular N-H⋯O hydrogen bond gives rise to a six-membered ring. In the crystal structure, two mol-ecules are connected by O-H⋯O hydrogen bonds, forming a centrosymmetric dimer. These dimers are further connected by C-H⋯O hydrogen bonds.

Related literature

For the synthesis and biological evaluation of sulfur-containing heterocyclic compounds, see: Zia-ur-Rehman et al. (2005 ▶, 2006 ▶, 2009 ▶); Xiao & Timberlake (2000 ▶); Lee & Lee (2002 ▶). For biological evaluation of sulfonamides, see: Hanson et al. (1999 ▶); Moree et al. (1991 ▶); Rough et al. (1998 ▶). For related literature on sulfonamides, see: Esteve & Bidal (2002 ▶); Soledade et al. (2006 ▶). For related structures, see: Gowda et al. (2007 ▶); Arshad et al. (2008 ▶).

Experimental

Crystal data

C8H9NO4S

M = 215.23

Triclinic,

a = 5.2001 (2) Å

b = 8.6120 (4) Å

c = 11.2314 (5) Å

α = 72.675 (3)°

β = 84.155 (3)°

γ = 86.846 (3)°

V = 477.50 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.19 × 0.09 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.941, T max = 0.993

9379 measured reflections

2330 independent reflections

1261 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.121

S = 1.01

2330 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 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: SHELXTL (Sheldrick, 2008 ▶) and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036113/bt5054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036113/bt5054Isup2.hkl

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

C8H9NO4S	Z = 2
Mr = 215.23	F(000) = 224
Triclinic, P1	Dx = 1.497 Mg m−3
Hall symbol: -P 1	Melting point: 373 K
a = 5.2001 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6120 (4) Å	Cell parameters from 2313 reflections
c = 11.2314 (5) Å	θ = 2.6–26.6°
α = 72.675 (3)°	µ = 0.33 mm−1
β = 84.155 (3)°	T = 296 K
γ = 86.846 (3)°	Needle, colourless
V = 477.50 (4) Å3	0.19 × 0.09 × 0.02 mm

Bruker APEXII CCD area-detector diffractometer	2330 independent reflections
Radiation source: fine-focus sealed tube	1261 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −6→6
Tmin = 0.941, Tmax = 0.993	k = −11→11
9379 measured reflections	l = −14→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.0282P] where P = (Fo2 + 2Fc2)/3
2330 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 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	0.13958 (10)	0.86241 (8)	0.36548 (6)	0.0718 (3)
O1	0.7317 (3)	0.9547 (2)	0.09332 (14)	0.0702 (4)
O2	0.9632 (3)	0.7901 (2)	0.00272 (17)	0.0884 (6)
H2	1.047 (6)	0.868 (4)	−0.020 (3)	0.106*
O3	0.1286 (4)	1.0325 (2)	0.3430 (2)	0.1179 (8)
O4	−0.0938 (3)	0.7780 (2)	0.38190 (16)	0.0881 (6)
N1	0.3205 (3)	0.8337 (2)	0.24607 (18)	0.0737 (6)
H1	0.3768	0.9197	0.1899	0.088*
C1	0.6130 (4)	0.6764 (3)	0.14278 (19)	0.0580 (6)
C2	0.3943 (4)	0.6848 (3)	0.22472 (19)	0.0579 (6)
C3	0.2556 (4)	0.5456 (3)	0.2809 (2)	0.0770 (7)
H3	0.1102	0.5498	0.3355	0.092*
C4	0.3279 (5)	0.4020 (3)	0.2577 (3)	0.0826 (7)
H4	0.2305	0.3101	0.2959	0.099*
C5	0.5438 (5)	0.3919 (3)	0.1784 (3)	0.0839 (8)
H5	0.5945	0.2937	0.1635	0.101*
C6	0.6818 (5)	0.5284 (3)	0.1222 (2)	0.0778 (7)
H6	0.8272	0.5219	0.0682	0.093*
C7	0.7712 (4)	0.8198 (3)	0.07879 (19)	0.0617 (6)
C8	0.3072 (5)	0.7722 (4)	0.4963 (3)	0.0931 (9)
H8A	0.4750	0.8186	0.4842	0.140*
H8B	0.3260	0.6573	0.5079	0.140*
H8C	0.2130	0.7910	0.5690	0.140*

	U11	U22	U33	U12	U13	U23
S1	0.0519 (3)	0.0691 (5)	0.0812 (5)	−0.0032 (3)	0.0323 (3)	−0.0144 (3)
O1	0.0596 (9)	0.0739 (11)	0.0679 (10)	−0.0159 (8)	0.0290 (7)	−0.0160 (8)
O2	0.0795 (11)	0.0919 (14)	0.0887 (13)	−0.0233 (9)	0.0491 (9)	−0.0336 (11)
O3	0.1275 (16)	0.0632 (12)	0.1399 (18)	−0.0009 (10)	0.0728 (14)	−0.0229 (11)
O4	0.0469 (8)	0.1114 (14)	0.0933 (13)	−0.0105 (8)	0.0251 (8)	−0.0194 (10)
N1	0.0676 (11)	0.0592 (12)	0.0772 (13)	−0.0082 (9)	0.0391 (10)	−0.0078 (10)
C1	0.0512 (11)	0.0722 (15)	0.0480 (12)	−0.0099 (10)	0.0099 (9)	−0.0167 (11)
C2	0.0486 (11)	0.0615 (14)	0.0558 (13)	−0.0077 (10)	0.0123 (9)	−0.0099 (10)
C3	0.0625 (13)	0.0719 (17)	0.0865 (18)	−0.0136 (12)	0.0254 (12)	−0.0161 (13)
C4	0.0825 (16)	0.0716 (17)	0.0894 (19)	−0.0235 (13)	0.0146 (14)	−0.0207 (14)
C5	0.0952 (19)	0.0732 (17)	0.0866 (18)	−0.0142 (14)	0.0148 (15)	−0.0340 (14)
C6	0.0761 (15)	0.0870 (19)	0.0708 (16)	−0.0099 (14)	0.0227 (13)	−0.0322 (14)
C7	0.0510 (11)	0.0813 (17)	0.0466 (12)	−0.0093 (11)	0.0156 (9)	−0.0146 (12)
C8	0.0601 (14)	0.132 (2)	0.089 (2)	−0.0001 (15)	0.0122 (13)	−0.0406 (18)

S1—O3	1.4091 (18)	C2—C3	1.381 (3)
S1—O4	1.4164 (16)	C3—C4	1.363 (3)
S1—N1	1.6307 (18)	C3—H3	0.9300
S1—C8	1.740 (3)	C4—C5	1.376 (3)
O1—C7	1.223 (3)	C4—H4	0.9300
O2—C7	1.312 (2)	C5—C6	1.361 (3)
O2—H2	0.78 (3)	C5—H5	0.9300
N1—C2	1.400 (3)	C6—H6	0.9300
N1—H1	0.8600	C8—H8A	0.9600
C1—C6	1.384 (3)	C8—H8B	0.9600
C1—C2	1.401 (3)	C8—H8C	0.9600
C1—C7	1.477 (3)
O3—S1—O4	119.14 (12)	C3—C4—C5	120.6 (2)
O3—S1—N1	104.71 (10)	C3—C4—H4	119.7
O4—S1—N1	109.48 (11)	C5—C4—H4	119.7
O3—S1—C8	109.48 (15)	C6—C5—C4	118.8 (2)
O4—S1—C8	107.25 (12)	C6—C5—H5	120.6
N1—S1—C8	106.10 (11)	C4—C5—H5	120.6
C7—O2—H2	107 (2)	C5—C6—C1	122.2 (2)
C2—N1—S1	127.27 (14)	C5—C6—H6	118.9
C2—N1—H1	116.4	C1—C6—H6	118.9
S1—N1—H1	116.4	O1—C7—O2	121.91 (19)
C6—C1—C2	118.5 (2)	O1—C7—C1	124.62 (18)
C6—C1—C7	119.46 (19)	O2—C7—C1	113.5 (2)
C2—C1—C7	122.1 (2)	S1—C8—H8A	109.5
C3—C2—N1	121.92 (19)	S1—C8—H8B	109.5
C3—C2—C1	118.7 (2)	H8A—C8—H8B	109.5
N1—C2—C1	119.34 (18)	S1—C8—H8C	109.5
C4—C3—C2	121.2 (2)	H8A—C8—H8C	109.5
C4—C3—H3	119.4	H8B—C8—H8C	109.5
C2—C3—H3	119.4
O3—S1—N1—C2	179.0 (2)	C1—C2—C3—C4	−0.1 (4)
O4—S1—N1—C2	−52.2 (2)	C2—C3—C4—C5	0.7 (4)
C8—S1—N1—C2	63.2 (2)	C3—C4—C5—C6	−0.9 (4)
S1—N1—C2—C3	22.1 (3)	C4—C5—C6—C1	0.4 (4)
S1—N1—C2—C1	−158.81 (18)	C2—C1—C6—C5	0.3 (4)
C6—C1—C2—C3	−0.4 (3)	C7—C1—C6—C5	180.0 (2)
C7—C1—C2—C3	179.9 (2)	C6—C1—C7—O1	−177.7 (2)
C6—C1—C2—N1	−179.6 (2)	C2—C1—C7—O1	2.0 (4)
C7—C1—C2—N1	0.7 (3)	C6—C1—C7—O2	2.3 (3)
N1—C2—C3—C4	179.1 (2)	C2—C1—C7—O2	−177.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.78 (3)	1.89 (3)	2.671 (2)	172 (4)
N1—H1···O1	0.86	2.03	2.652 (2)	128
C4—H4···O3ii	0.93	2.37	3.235 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.78 (3)	1.89 (3)	2.671 (2)	172 (4)
N1—H1⋯O1	0.86	2.03	2.652 (2)	128
C4—H4⋯O3ii	0.93	2.37	3.235 (3)	155

Symmetry codes: (i) ; (ii) .