N,N-Dimethyl­acetamide–4-iodo­benzene­sulfonic acid–water (1/1/1)

Rui Liu; Yu-Feng Li; Wei Luo; Jin Chang; Hong-Jun Zhu

doi:10.1107/S160053680803701X

. 2008 Nov 20;64(Pt 12):o2376. doi: 10.1107/S160053680803701X

N,N-Dimethylacetamide–4-iodobenzenesulfonic acid–water (1/1/1)

Rui Liu ^a, Yu-Feng Li ^a, Wei Luo ^a, Jin Chang ^a, Hong-Jun Zhu ^a,^*

PMCID: PMC2960060 PMID: 21581348

Abstract

In the title compound, C₆H₅IO₃S·C₄H₉NO·H₂O, N,N-dimethylacetamide and 4-iodobenzenesulfonic acidmolecules are linked by an intramolecular C—H⋯O hydrogen bond. In the crystal structure, intermolecular O—H⋯O, O—H⋯I and C—H⋯O hydrogen bonds link the molecules.

Related literature

For a related structure, see: Wu et al. (2000 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₆H₅IO₃S·C₄H₉NO·H₂O
M _r = 389.21
Orthorhombic,
a = 14.173 (3) Å
b = 7.7480 (15) Å
c = 13.272 (3) Å
V = 1457.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.35 mm⁻¹
T = 294 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.539, T _max = 0.799
1490 measured reflections
1490 independent reflections
1096 reflections with I > 2σ(I)
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.162
S = 1.07
1490 reflections
172 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.53 e Å⁻³
Δρ_min = −2.42 e Å⁻³
Absolute structure: Flack (1983 ▶), 7 Friedel pairs
Flack parameter: 0.13 (10)

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803701X/hk2535sup1.cif

e-64-o2376-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803701X/hk2535Isup2.hkl

e-64-o2376-Isup2.hkl^{(73.5KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2ⁱ	0.87 (13)	1.97 (15)	2.765 (16)	151 (14)
O1W—H1WB⋯O3ⁱⁱ	0.94 (10)	1.85 (15)	2.657 (16)	143 (17)
O2—H2A⋯I1ⁱⁱⁱ	0.85	2.57	3.208 (16)	133
C1—H1B⋯O3^iv	0.93	2.46	3.378 (15)	168
C5—H5A⋯O1^v	0.93	2.55	3.192 (17)	126
C9—H9A⋯O3	0.96	2.56	3.48 (2)	161

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The crystal structure of the title compound with a comb-like structure illustrate the three different components linked by weak interactions based on hydrogen bonds. Furthermore, the hydrolysis mechanism of the innersalt, which was formed from 4-iodobenzenesulfonyl chloride and N,N-dimethylacetamide, was understood (Wu et al., 2000). Meanwhile, the complicated hydrolysate was finally confirmed. We report herein its crystal structure.

The asymmetric unit of the title compound contains N,N-dimethylacetamide, 4-iodobenzenesulfonic acid and water molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C1-C6) is, of course, planar. The intramolecular C-H···O hydrogen bonds (Table 1) result in the formation of two nonplanar five-membered rings B (S/O1/C2/C3/H2B) and C (O4/N1/C8/C10/H8A), having envelope conformations with O1 and H8A atoms displaced by 0.193 (3) and 0.194 (3) Å, respectively, from the planes of the other ring atoms.

In the crystal structure, intermolecular O-H···O, O-H···I and C-H···O hydrogen bonds link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. As can be seen from the packing diagram (Fig. 3), the molecules are stacked along the b axis. The comb-like structure depends on C-H···O hydrogen bonds. The 4-iodobenzenesulfonic acid molecules constitute the main chain and the N,N-dimethylacetamide molecules intermesh to each other as the branches.

Experimental

Addition of N,N-dimethylacetamide (1.8 ml, 0.02 mol) into 4-iodobenzenesulfonyl chloride (6.1 g, 0.02 mol) gave milk-white solution of innersalt (Wu et al., 2000). The innersalt was dissolved in acetone (20 ml) and placed in moist chamber to crystallize. The crystals were obtained by evaporating solvent slowly at room temperature for about 40 d.