2-(2-Iodo-benzenesulfonamido)acetic acid.

The title compound, C(8)H(8)INO(4)S, is a halogenated sulfon-amide, a medicinally important class of organic compounds. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds involving the carboxylic acid groups form characteristic centrosymmetric dimers. These dimers are further linked through centrosymmetric dimeric N-H⋯O inter-actions involving the amido H atom and a sulfonyl O atom. This leads to the formation of a ribbon-like polymer structure propagating in the b direction.

Related literature

For background on sulfonamides, or sulfa drugs, see: Pandya et al. (2003 ▶). For the structure of the non-halogenated analogue, see: Arshad et al. (2008b ▶). For the synthesis of the title compound, see: Deng & Mani (2006 ▶). For details of related structures: see Arshad et al. (2008a ▶,c ▶). For background on related thia­zine heterocycles, see: Arshad et al. (2008d ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H8INO4S

M = 341.11

Triclinic,

a = 5.5877 (2) Å

b = 8.0145 (2) Å

c = 12.3584 (4) Å

α = 80.923 (2)°

β = 83.398 (2)°

γ = 88.038 (2)°

V = 542.81 (3) Å3

Z = 2

Mo Kα radiation

μ = 3.14 mm−1

T = 296 K

0.22 × 0.10 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.691, T max = 0.834

11492 measured reflections

2691 independent reflections

2297 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.086

S = 1.02

2691 reflections

137 parameters

H-atom parameters constrained

Δρmax = 1.43 e Å−3

Δρmin = −1.09 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005248/su2093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005248/su2093Isup2.hkl

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

C8H8INO4S	Z = 2
Mr = 341.11	F(000) = 328
Triclinic, P1	Dx = 2.087 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5877 (2) Å	Cell parameters from 6313 reflections
b = 8.0145 (2) Å	θ = 2.6–28.3°
c = 12.3584 (4) Å	µ = 3.14 mm−1
α = 80.923 (2)°	T = 296 K
β = 83.398 (2)°	Needle-like, light brown
γ = 88.038 (2)°	0.22 × 0.10 × 0.06 mm
V = 542.81 (3) Å3

Bruker Kappa APEXII CCD diffractometer	2691 independent reflections
Radiation source: fine-focus sealed tube	2297 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.691, Tmax = 0.834	k = −10→10
11492 measured 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0454P)2 + 0.6546P] where P = (Fo2 + 2Fc2)/3
2691 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 1.43 e Å−3
0 restraints	Δρmin = −1.09 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 esds are taken into account in the estimation of distances, angles and torsion angles

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
I1	0.10590 (5)	0.34414 (3)	0.90179 (2)	0.0537 (1)
S1	0.59293 (13)	0.42594 (9)	0.68657 (7)	0.0327 (2)
O1	0.5522 (4)	0.7909 (3)	0.5250 (2)	0.0405 (7)
O2	0.2240 (4)	0.9320 (3)	0.5837 (3)	0.0506 (8)
O3	0.6165 (5)	0.5362 (3)	0.7649 (2)	0.0447 (8)
O4	0.7874 (4)	0.4121 (3)	0.6022 (2)	0.0448 (8)
N1	0.3478 (5)	0.4818 (3)	0.6322 (2)	0.0348 (8)
C1	0.5418 (5)	0.2165 (4)	0.7568 (3)	0.0319 (8)
C2	0.3582 (6)	0.1730 (4)	0.8409 (3)	0.0376 (9)
C3	0.3352 (8)	0.0057 (4)	0.8907 (3)	0.0496 (11)
C4	0.4944 (8)	−0.1169 (4)	0.8574 (3)	0.0520 (13)
C5	0.6787 (8)	−0.0735 (4)	0.7758 (4)	0.0514 (11)
C6	0.7032 (7)	0.0926 (4)	0.7254 (3)	0.0434 (10)
C7	0.2290 (6)	0.6417 (4)	0.6433 (3)	0.0371 (9)
C8	0.3550 (6)	0.7946 (4)	0.5770 (3)	0.0346 (9)
H1N	0.28640	0.41450	0.59550	0.0420*
H2O	0.29800	1.01380	0.54930	0.0760*
H3	0.21160	−0.02410	0.94690	0.0600*
H4	0.47630	−0.22890	0.89050	0.0630*
H5	0.78740	−0.15580	0.75430	0.0620*
H6	0.82870	0.12170	0.67000	0.0520*
H7A	0.21220	0.65480	0.72050	0.0440*
H7B	0.06810	0.63890	0.62140	0.0440*

	U11	U22	U33	U12	U13	U23
I1	0.0578 (2)	0.0421 (2)	0.0529 (2)	0.0132 (1)	0.0143 (1)	0.0003 (1)
S1	0.0304 (3)	0.0232 (3)	0.0442 (4)	−0.0049 (3)	−0.0027 (3)	−0.0042 (3)
O1	0.0375 (12)	0.0252 (10)	0.0551 (14)	−0.0047 (9)	0.0058 (10)	−0.0016 (9)
O2	0.0413 (13)	0.0247 (11)	0.0772 (18)	0.0014 (9)	0.0106 (12)	0.0057 (11)
O3	0.0498 (14)	0.0282 (11)	0.0602 (16)	−0.0014 (10)	−0.0147 (12)	−0.0130 (10)
O4	0.0337 (11)	0.0411 (13)	0.0565 (15)	−0.0076 (10)	0.0046 (10)	−0.0034 (11)
N1	0.0353 (13)	0.0217 (11)	0.0466 (15)	−0.0039 (9)	−0.0051 (11)	−0.0016 (10)
C1	0.0348 (15)	0.0227 (12)	0.0391 (16)	0.0011 (11)	−0.0065 (12)	−0.0059 (11)
C2	0.0442 (17)	0.0279 (14)	0.0394 (17)	0.0028 (12)	−0.0029 (13)	−0.0035 (12)
C3	0.063 (2)	0.0326 (17)	0.048 (2)	−0.0015 (15)	0.0038 (17)	0.0022 (14)
C4	0.075 (3)	0.0260 (16)	0.054 (2)	0.0038 (16)	−0.009 (2)	−0.0024 (14)
C5	0.062 (2)	0.0287 (16)	0.065 (2)	0.0135 (15)	−0.0084 (19)	−0.0137 (16)
C6	0.0454 (18)	0.0322 (16)	0.052 (2)	0.0049 (13)	0.0002 (15)	−0.0102 (14)
C7	0.0333 (15)	0.0247 (13)	0.0495 (18)	−0.0027 (11)	0.0011 (13)	0.0018 (12)
C8	0.0343 (15)	0.0229 (13)	0.0449 (17)	−0.0033 (11)	−0.0040 (13)	−0.0002 (12)

I1—C2	2.094 (3)	C2—C3	1.388 (5)
S1—O3	1.429 (3)	C3—C4	1.382 (5)
S1—O4	1.431 (2)	C4—C5	1.369 (6)
S1—N1	1.613 (3)	C5—C6	1.382 (5)
S1—C1	1.780 (3)	C7—C8	1.509 (5)
O1—C8	1.212 (4)	C3—H3	0.9300
O2—C8	1.310 (4)	C4—H4	0.9300
O2—H2O	0.8200	C5—H5	0.9300
N1—C7	1.442 (4)	C6—H6	0.9300
N1—H1N	0.8600	C7—H7A	0.9700
C1—C6	1.389 (5)	C7—H7B	0.9700
C1—C2	1.385 (5)
O3—S1—O4	118.92 (15)	C1—C6—C5	120.5 (4)
O3—S1—N1	106.70 (15)	N1—C7—C8	115.3 (3)
O3—S1—C1	109.54 (16)	O1—C8—O2	124.4 (3)
O4—S1—N1	110.20 (14)	O1—C8—C7	124.5 (3)
O4—S1—C1	105.65 (15)	O2—C8—C7	111.1 (3)
N1—S1—C1	105.02 (13)	C2—C3—H3	120.00
C8—O2—H2O	109.00	C4—C3—H3	120.00
S1—N1—C7	121.8 (2)	C3—C4—H4	120.00
C7—N1—H1N	119.00	C5—C4—H4	120.00
S1—N1—H1N	119.00	C4—C5—H5	120.00
C2—C1—C6	119.5 (3)	C6—C5—H5	120.00
S1—C1—C6	116.4 (3)	C1—C6—H6	120.00
S1—C1—C2	124.1 (2)	C5—C6—H6	120.00
I1—C2—C1	124.6 (2)	N1—C7—H7A	108.00
I1—C2—C3	116.0 (3)	N1—C7—H7B	108.00
C1—C2—C3	119.5 (3)	C8—C7—H7A	108.00
C2—C3—C4	120.5 (4)	C8—C7—H7B	108.00
C3—C4—C5	120.1 (3)	H7A—C7—H7B	107.00
C4—C5—C6	120.0 (4)
O3—S1—N1—C7	15.3 (3)	C6—C1—C2—I1	178.1 (3)
O4—S1—N1—C7	−115.1 (3)	C6—C1—C2—C3	−1.5 (5)
C1—S1—N1—C7	131.6 (3)	S1—C1—C6—C5	179.6 (3)
O3—S1—C1—C2	54.6 (3)	C2—C1—C6—C5	1.3 (5)
O3—S1—C1—C6	−123.6 (3)	I1—C2—C3—C4	−179.3 (3)
O4—S1—C1—C2	−176.2 (3)	C1—C2—C3—C4	0.3 (6)
O4—S1—C1—C6	5.6 (3)	C2—C3—C4—C5	0.9 (6)
N1—S1—C1—C2	−59.7 (3)	C3—C4—C5—C6	−1.1 (6)
N1—S1—C1—C6	122.1 (3)	C4—C5—C6—C1	−0.1 (6)
S1—N1—C7—C8	72.2 (4)	N1—C7—C8—O1	−6.5 (5)
S1—C1—C2—I1	0.0 (4)	N1—C7—C8—O2	174.0 (3)
S1—C1—C2—C3	−179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.47	3.142 (3)	135
O2—H2O···O1ii	0.82	1.86	2.676 (4)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.47	3.142 (3)	135
O2—H2O⋯O1ii	0.82	1.86	2.676 (4)	176

Symmetry codes: (i) ; (ii) .