4-(2-Iodo-benzene-sulfonamido)benzoic acid monohydrate.

In the mol-ecule of the title compound, C(13)H(10)INO(4)S·H(2)O, the coordination around the S atom is distorted tetra-hedral. The aromatic rings are oriented at a dihedral angle of 74.18 (17)°. Intra-molecular C-H⋯O hydrogen bonds result in the formation of non-planar five- and six-membered rings, which adopt envelope and twist conformations, respectively. In the crystal structure, inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules. π-π Contacts between the phenyl rings [centroid-centroid distance = 3.726 (3) Å] may further stabilize the structure. There is also a C-H⋯π inter-action.

Related literature

For general background, see: Medina et al. (1999 ▶). For related structures, see: Arshad et al. (2008a ▶,b ▶); Nan & Xing (2006 ▶); Deng & n class="Species">Mani (2006 ▶).

Experimental

Crystal data

C13H10INO4S·n class="Chemical">H2O

M = 421.20

Monoclinic,

a = 13.8049 (9) Å

b = 8.2756 (5) Å

c = 14.7928 (10) Å

β = 117.472 (3)°

V = 1499.42 (17) Å3

Z = 4

Mo Kα radiation

μ = 2.30 mm−1

T = 296 (2) K

0.28 × 0.10 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.754, T max = 0.849

9099 measured reflections

3687 independent reflections

2022 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.112

S = 1.01

3687 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; 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, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043754/hk2605sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043754/hk2605Isup2.hkl

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

C13H10INO4S·H2O	F(000) = 824
Mr = 421.20	Dx = 1.866 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3638 reflections
a = 13.8049 (9) Å	θ = 2.8–28.3°
b = 8.2756 (5) Å	µ = 2.30 mm−1
c = 14.7928 (10) Å	T = 296 K
β = 117.472 (3)°	Needle, light brown
V = 1499.42 (17) Å3	0.28 × 0.10 × 0.07 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3687 independent reflections
Radiation source: fine-focus sealed tube	2022 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 2.8°
ω scans	h = −15→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→6
Tmin = 0.754, Tmax = 0.849	l = −19→19
9099 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0445P)2] where P = (Fo2 + 2Fc2)/3
3687 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.55 e Å−3
1 restraint	Δρmin = −0.54 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 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	0.05915 (3)	−0.04749 (5)	0.26394 (3)	0.0542 (2)
S1	0.25343 (9)	0.13703 (16)	0.19929 (10)	0.0345 (4)
O1	0.3085 (3)	0.2410 (4)	0.1612 (3)	0.0454 (14)
O2	0.2710 (3)	−0.0328 (4)	0.2010 (3)	0.0415 (11)
O3	0.4294 (3)	0.7980 (5)	0.6032 (3)	0.0614 (17)
O4	0.3555 (4)	0.9284 (5)	0.4580 (3)	0.0710 (17)
O5	0.4923 (3)	0.4220 (5)	0.1937 (3)	0.086 (2)
N1	0.2852 (3)	0.1876 (5)	0.3139 (3)	0.0377 (16)
C1	0.1119 (4)	0.1750 (5)	0.1231 (4)	0.0292 (17)
C2	0.0316 (4)	0.1050 (6)	0.1405 (4)	0.0363 (19)
C3	−0.0775 (4)	0.1337 (7)	0.0725 (5)	0.051 (2)
C4	−0.1052 (5)	0.2319 (8)	−0.0099 (5)	0.056 (2)
C5	−0.0257 (5)	0.2994 (7)	−0.0279 (4)	0.054 (2)
C6	0.0834 (4)	0.2707 (6)	0.0389 (4)	0.044 (2)
C7	0.3051 (3)	0.3426 (6)	0.3580 (4)	0.0331 (18)
C8	0.3537 (4)	0.3529 (6)	0.4634 (4)	0.0392 (19)
C9	0.3778 (4)	0.5001 (6)	0.5106 (4)	0.0378 (17)
C10	0.3543 (3)	0.6425 (6)	0.4554 (4)	0.0327 (16)
C11	0.3061 (4)	0.6315 (6)	0.3498 (4)	0.0391 (19)
C12	0.2810 (4)	0.4842 (6)	0.3012 (4)	0.0397 (17)
C13	0.3791 (4)	0.8042 (7)	0.5038 (5)	0.0417 (19)
H1	0.29097	0.10916	0.35421	0.0453*
H3	−0.13213	0.08538	0.08334	0.0614*
H3O	0.440 (5)	0.896 (8)	0.634 (5)	0.0734*
H4	−0.17827	0.25271	−0.05378	0.0676*
H5	−0.04448	0.36446	−0.08481	0.0649*
H6	0.13757	0.31670	0.02652	0.0534*
H8	0.36997	0.25903	0.50216	0.0469*
H9	0.41064	0.50465	0.58138	0.0457*
H11	0.29045	0.72558	0.31126	0.0474*
H12	0.24791	0.47936	0.23047	0.0474*
H5A	0.55225	0.43714	0.24163	0.1030*
H5B	0.44825	0.35754	0.20513	0.1030*

	U11	U22	U33	U12	U13	U23
I1	0.0626 (3)	0.0469 (3)	0.0680 (3)	0.0006 (2)	0.0429 (2)	0.0116 (2)
S1	0.0343 (6)	0.0313 (8)	0.0384 (9)	−0.0025 (6)	0.0171 (6)	−0.0039 (6)
O1	0.049 (2)	0.043 (2)	0.056 (3)	−0.0132 (17)	0.0343 (19)	−0.0061 (19)
O2	0.0403 (19)	0.029 (2)	0.050 (2)	0.0031 (16)	0.0165 (17)	−0.0062 (18)
O3	0.086 (3)	0.032 (3)	0.043 (3)	0.003 (2)	0.010 (2)	−0.007 (2)
O4	0.105 (3)	0.027 (3)	0.045 (3)	0.005 (2)	0.004 (2)	0.005 (2)
O5	0.046 (2)	0.076 (4)	0.100 (4)	−0.015 (2)	0.003 (2)	0.054 (3)
N1	0.053 (3)	0.023 (2)	0.029 (3)	−0.0021 (19)	0.012 (2)	0.003 (2)
C1	0.035 (3)	0.024 (3)	0.028 (3)	0.002 (2)	0.014 (2)	−0.001 (2)
C2	0.039 (3)	0.028 (3)	0.044 (4)	0.002 (2)	0.021 (3)	−0.007 (2)
C3	0.043 (3)	0.042 (4)	0.070 (5)	−0.003 (3)	0.027 (3)	−0.016 (3)
C4	0.046 (3)	0.051 (4)	0.049 (4)	0.008 (3)	0.002 (3)	−0.011 (3)
C5	0.073 (4)	0.041 (4)	0.032 (4)	0.009 (3)	0.010 (3)	−0.001 (3)
C6	0.054 (3)	0.037 (4)	0.040 (4)	−0.005 (3)	0.020 (3)	−0.003 (3)
C7	0.030 (2)	0.028 (3)	0.038 (4)	0.000 (2)	0.013 (2)	−0.004 (3)
C8	0.052 (3)	0.023 (3)	0.041 (4)	0.001 (2)	0.020 (3)	0.006 (3)
C9	0.050 (3)	0.028 (3)	0.033 (3)	0.000 (2)	0.017 (3)	0.001 (2)
C10	0.028 (2)	0.032 (3)	0.035 (3)	−0.002 (2)	0.012 (2)	−0.002 (3)
C11	0.044 (3)	0.023 (3)	0.046 (4)	0.000 (2)	0.017 (3)	0.007 (3)
C12	0.050 (3)	0.033 (3)	0.027 (3)	0.001 (2)	0.010 (3)	0.003 (2)
C13	0.036 (3)	0.030 (3)	0.048 (4)	0.004 (2)	0.010 (3)	0.002 (3)

I1—C2	2.105 (5)	C5—C6	1.389 (9)
S1—O1	1.425 (4)	C7—C8	1.387 (7)
S1—O2	1.425 (4)	C7—C12	1.390 (7)
S1—N1	1.599 (4)	C8—C9	1.367 (7)
S1—C1	1.776 (6)	C9—C10	1.384 (7)
O3—C13	1.306 (8)	C10—C13	1.481 (8)
O4—C13	1.191 (7)	C10—C11	1.390 (7)
O3—H3O	0.91 (7)	C11—C12	1.376 (7)
O5—H5A	0.8100	C3—H3	0.9300
O5—H5B	0.8800	C4—H4	0.9300
N1—C7	1.408 (6)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
C1—C2	1.376 (8)	C8—H8	0.9300
C1—C6	1.372 (7)	C9—H9	0.9300
C2—C3	1.392 (9)	C11—H11	0.9300
C3—C4	1.365 (9)	C12—H12	0.9300
C4—C5	1.363 (10)
I1···O2	3.456 (5)	C4···O2iv	3.158 (8)
I1···N1	3.456 (4)	C4···I1xi	3.853 (7)
I1···C4i	3.853 (7)	C5···C5xii	3.416 (8)
I1···C2i	3.671 (5)	C8···O1xiii	3.353 (7)
I1···C3i	3.509 (6)	C9···C9x	3.530 (9)
I1···H1	3.1200	C12···O1	3.035 (7)
S1···H12	2.8800	C13···O5v	3.379 (7)
S1···H5Aii	2.9200	C9···H3xi	3.1000
O1···O5	2.791 (6)	C10···H3xi	2.8900
O1···C12	3.035 (7)	C11···H3xi	3.0100
O1···C8iii	3.353 (7)	H1···I1	3.1200
O2···C4iv	3.158 (8)	H1···H8	2.3100
O2···O5ii	2.924 (6)	H1···O4ix	2.0300
O2···I1	3.456 (5)	H3···C10i	2.8900
O3···O5v	2.616 (6)	H3···C9i	3.1000
O4···N1vi	2.860 (6)	H3···C11i	3.0100
O5···O3vii	2.616 (6)	H3O···O5v	1.73 (7)
O5···C13vii	3.379 (7)	H3O···H5Av	2.1400
O5···O2viii	2.924 (6)	H3O···H5Bv	2.2700
O5···O1	2.791 (6)	H4···O2iv	2.6700
O1···H12	2.5400	H5A···O2viii	2.2000
O1···H5B	1.9800	H5A···H9x	2.4700
O1···H6	2.3600	H5A···S1viii	2.9200
O1···H8iii	2.8500	H5A···H3Ovii	2.1400
O2···H4iv	2.6700	H5B···O1	1.9800
O2···H11ix	2.5200	H5B···O3x	2.8500
O2···H5Aii	2.2000	H5B···H3Ovii	2.2700
O3···H9	2.4500	H6···O1	2.3600
O3···H5Bx	2.8500	H8···O4ix	2.8000
O4···H1vi	2.0300	H8···H1	2.3100
O4···H8vi	2.8000	H8···O1xiii	2.8500
O4···H11	2.5600	H9···O3	2.4500
O5···H3Ovii	1.73 (7)	H9···H5Ax	2.4700
N1···O4ix	2.860 (6)	H11···O2vi	2.5200
N1···I1	3.456 (4)	H11···O4	2.5600
C2···I1xi	3.671 (5)	H12···O1	2.5400
C3···I1xi	3.509 (6)	H12···S1	2.8800
O1—S1—O2	119.0 (3)	C8—C9—C10	121.5 (5)
O1—S1—N1	109.0 (2)	C9—C10—C11	117.9 (5)
O1—S1—C1	105.9 (2)	C11—C10—C13	119.1 (5)
O2—S1—N1	106.2 (2)	C9—C10—C13	123.0 (5)
O2—S1—C1	108.3 (2)	C10—C11—C12	121.3 (5)
N1—S1—C1	108.1 (3)	C7—C12—C11	119.9 (5)
C13—O3—H3O	114 (4)	O3—C13—C10	113.2 (5)
H5A—O5—H5B	116.00	O4—C13—C10	124.3 (6)
S1—N1—C7	129.0 (4)	O3—C13—O4	122.6 (6)
C7—N1—H1	116.00	C2—C3—H3	120.00
S1—N1—H1	115.00	C4—C3—H3	120.00
S1—C1—C2	123.5 (4)	C5—C4—H4	120.00
S1—C1—C6	116.7 (5)	C3—C4—H4	120.00
C2—C1—C6	119.6 (5)	C4—C5—H5	120.00
I1—C2—C1	125.2 (4)	C6—C5—H5	120.00
C1—C2—C3	119.3 (5)	C5—C6—H6	120.00
I1—C2—C3	115.6 (4)	C1—C6—H6	120.00
C2—C3—C4	120.7 (6)	C7—C8—H8	120.00
C3—C4—C5	120.0 (6)	C9—C8—H8	120.00
C4—C5—C6	119.9 (5)	C10—C9—H9	119.00
C1—C6—C5	120.5 (6)	C8—C9—H9	119.00
C8—C7—C12	119.0 (5)	C10—C11—H11	119.00
N1—C7—C8	117.8 (4)	C12—C11—H11	119.00
N1—C7—C12	123.2 (5)	C7—C12—H12	120.00
C7—C8—C9	120.4 (5)	C11—C12—H12	120.00
O1—S1—N1—C7	35.5 (5)	C1—C2—C3—C4	−0.9 (9)
O2—S1—N1—C7	164.9 (5)	C2—C3—C4—C5	1.9 (10)
C1—S1—N1—C7	−79.1 (5)	C3—C4—C5—C6	−1.3 (9)
O1—S1—C1—C2	−175.7 (4)	C4—C5—C6—C1	−0.1 (8)
O1—S1—C1—C6	9.1 (4)	N1—C7—C8—C9	178.2 (5)
O2—S1—C1—C2	55.6 (5)	C12—C7—C8—C9	−0.2 (9)
O2—S1—C1—C6	−119.7 (4)	N1—C7—C12—C11	−177.8 (5)
N1—S1—C1—C2	−59.0 (5)	C8—C7—C12—C11	0.4 (9)
N1—S1—C1—C6	125.7 (4)	C7—C8—C9—C10	0.3 (9)
S1—N1—C7—C8	−166.5 (4)	C8—C9—C10—C11	−0.6 (9)
S1—N1—C7—C12	11.8 (8)	C8—C9—C10—C13	180.0 (6)
S1—C1—C2—I1	4.0 (6)	C9—C10—C11—C12	0.9 (9)
S1—C1—C2—C3	−175.7 (4)	C13—C10—C11—C12	−179.7 (6)
C6—C1—C2—I1	179.1 (4)	C9—C10—C13—O3	2.8 (8)
C6—C1—C2—C3	−0.5 (8)	C9—C10—C13—O4	−176.6 (6)
S1—C1—C6—C5	176.5 (4)	C11—C10—C13—O3	−176.6 (5)
C2—C1—C6—C5	1.0 (8)	C11—C10—C13—O4	4.0 (9)
I1—C2—C3—C4	179.4 (5)	C10—C11—C12—C7	−0.8 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ix	0.86	2.03	2.860 (6)	161.00
O3—H3O···O5v	0.91 (7)	1.73 (7)	2.616 (6)	165 (7)
O5—H5A···O2viii	0.81	2.20	2.924 (6)	149.00
O5—H5B···O1	0.88	1.98	2.791 (6)	152.00
C6—H6···O1	0.93	2.36	2.793 (7)	108.00
C11—H11···O2vi	0.93	2.52	3.437 (6)	171.00
C12—H12···O1	0.93	2.54	3.035 (7)	114.00
C3—H3···Cg2i	0.93	2.90	3.818 (7)	168.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.86	2.03	2.860 (6)	161.00
O3—H3O⋯O5ii	0.91 (7)	1.73 (7)	2.616 (6)	165 (7)
O5—H5A⋯O2iii	0.81	2.20	2.924 (6)	149.00
O5—H5B⋯O1	0.88	1.98	2.791 (6)	152.00
C6—H6⋯O1	0.93	2.36	2.793 (7)	108.00
C11—H11⋯O2iv	0.93	2.52	3.437 (6)	171.00
C12—H12⋯O1	0.93	2.54	3.035 (7)	114.00
C3—H3⋯Cg2v	0.93	2.90	3.818 (7)	168.00

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg2 is the centroid of the C7–C12 ring.