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

Liu, R.; Li, Y.-F.; Luo, W.; Chang, J.; Zhu, H.-J.

doi:10.1107/S160053680803701X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2376

doi:10.1107/S160053680803701X

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

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

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 19 September 2008; accepted 10 November 2008; online 20 November 2008)

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, P c a 2₁
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[F² > 2σ(F²)] = 0.063
wR(F²) = 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)

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
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+1, z-1]$ ; (ii) x+1, y-1, z-1; (iii) $[-x+{\script{1\over 2}}, y+1, z+{\script{1\over 2}}]$ ; (iv) x, y-1, z; (v) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

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).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
	Fig. 3. A packing diagram of the title compound, showing the formation of the supramolecular comb-like structure. For the sake of clarity, water molecules have been omitted.

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

Crystal data top

C₆H₅IO₃S·C₄H₉NO·H₂O	D_x = 1.774 Mg m⁻³
M_r = 389.21	Melting point: 363 K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 14.173 (3) Å	θ = 10–13°
b = 7.7480 (15) Å	µ = 2.35 mm⁻¹
c = 13.272 (3) Å	T = 294 K
V = 1457.4 (5) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm
F(000) = 768

Data collection top

Enraf–Nonius CAD-4 diffractometer	1096 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.9°, θ_min = 2.6°
ω/2θ scans	h = 0→17
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.539, T_max = 0.799	l = 0→16
1490 measured reflections	3 standard reflections every 120 min
1490 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.1045P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1490 reflections	Δρ_max = 1.53 e Å⁻³
172 parameters	Δρ_min = −2.42 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 7 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.13 (10)

Crystal data top

C₆H₅IO₃S·C₄H₉NO·H₂O	V = 1457.4 (5) Å³
M_r = 389.21	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 14.173 (3) Å	µ = 2.35 mm⁻¹
b = 7.7480 (15) Å	T = 294 K
c = 13.272 (3) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1096 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.539, T_max = 0.799	3 standard reflections every 120 min
1490 measured reflections	intensity decay: none
1490 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.162	Δρ_max = 1.53 e Å⁻³
S = 1.07	Δρ_min = −2.42 e Å⁻³
1490 reflections	Absolute structure: Flack (1983), 7 Friedel pairs
172 parameters	Absolute structure parameter: 0.13 (10)
4 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.20688 (5)	0.25040 (11)	0.7328 (2)	0.0505 (3)
S	0.1876 (2)	0.9056 (4)	1.0531 (3)	0.0438 (8)
O1W	0.9586 (8)	0.1582 (19)	0.0789 (10)	0.077 (4)
H1WA	0.914 (10)	0.084 (19)	0.065 (17)	0.093*
H1WB	1.023 (7)	0.13 (2)	0.082 (15)	0.093*
O1	0.1588 (10)	0.8396 (14)	1.1505 (8)	0.076 (4)
O2	0.2802 (7)	0.9782 (15)	1.0512 (14)	0.094 (5)
H2A	0.2768	1.0848	1.0659	0.113*
O3	0.1189 (8)	1.0230 (11)	1.0115 (8)	0.053 (2)
O4	−0.0108 (7)	0.6431 (14)	0.7131 (8)	0.060 (3)
N1	−0.0502 (9)	0.597 (2)	0.8736 (12)	0.070 (4)
C1	0.1840 (9)	0.4229 (16)	0.9376 (10)	0.041 (3)
H1B	0.1756	0.3110	0.9613	0.050*
C2	0.1806 (9)	0.5632 (16)	1.0022 (10)	0.043 (3)
H2B	0.1709	0.5450	1.0706	0.051*
C3	0.1912 (8)	0.7263 (14)	0.9674 (11)	0.034 (3)
C4	0.2059 (8)	0.7609 (14)	0.8682 (12)	0.038 (3)
H4A	0.2132	0.8741	0.8461	0.046*
C5	0.2100 (8)	0.6222 (17)	0.7992 (10)	0.044 (3)
H5A	0.2188	0.6412	0.7306	0.053*
C6	0.2002 (8)	0.4547 (15)	0.8381 (10)	0.038 (3)
C7	−0.0714 (13)	0.648 (3)	0.9756 (12)	0.078 (5)
H7A	−0.1176	0.7386	0.9748	0.117*
H7B	−0.0149	0.6890	1.0076	0.117*
H7C	−0.0956	0.5509	1.0121	0.117*
C8	−0.0515 (12)	0.407 (2)	0.8500 (15)	0.073 (5)
H8A	−0.0490	0.3903	0.7784	0.110*
H8B	−0.1084	0.3562	0.8760	0.110*
H8C	0.0020	0.3519	0.8808	0.110*
C9	−0.0327 (13)	0.897 (2)	0.8184 (15)	0.072 (5)
H9A	0.0203	0.9300	0.8590	0.107*
H9B	−0.0901	0.9276	0.8522	0.107*
H9C	−0.0296	0.9548	0.7546	0.107*
C10	−0.0305 (12)	0.705 (2)	0.8017 (15)	0.062 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0651 (5)	0.0364 (4)	0.0499 (5)	0.0024 (4)	−0.0001 (8)	−0.0136 (4)
S	0.0544 (17)	0.0296 (14)	0.0473 (17)	0.0041 (14)	−0.0096 (18)	−0.0142 (15)
O1W	0.054 (6)	0.103 (10)	0.075 (9)	0.002 (7)	0.005 (6)	−0.025 (8)
O1	0.141 (11)	0.047 (6)	0.039 (6)	0.028 (7)	0.002 (6)	−0.003 (5)
O2	0.076 (8)	0.059 (7)	0.147 (13)	0.004 (6)	−0.020 (9)	−0.062 (9)
O3	0.062 (6)	0.035 (5)	0.060 (6)	0.008 (4)	−0.006 (5)	−0.011 (4)
O4	0.065 (6)	0.060 (6)	0.055 (7)	0.006 (5)	0.000 (5)	0.001 (6)
N1	0.052 (8)	0.083 (10)	0.074 (10)	−0.008 (8)	−0.016 (7)	0.003 (9)
C1	0.057 (7)	0.024 (6)	0.043 (7)	−0.009 (6)	0.001 (6)	0.000 (5)
C2	0.064 (8)	0.034 (7)	0.030 (6)	0.003 (6)	−0.006 (6)	0.003 (6)
C3	0.031 (6)	0.025 (6)	0.045 (7)	0.004 (5)	−0.002 (5)	−0.006 (5)
C4	0.049 (7)	0.017 (5)	0.048 (8)	−0.001 (5)	0.000 (6)	−0.003 (5)
C5	0.051 (8)	0.042 (7)	0.039 (7)	0.006 (6)	−0.004 (6)	−0.003 (6)
C6	0.049 (7)	0.024 (6)	0.041 (7)	−0.002 (5)	−0.002 (6)	−0.006 (6)
C7	0.082 (12)	0.101 (15)	0.051 (10)	−0.005 (11)	0.018 (9)	−0.004 (10)
C8	0.061 (10)	0.070 (11)	0.089 (13)	−0.011 (9)	0.000 (9)	0.008 (11)
C9	0.078 (12)	0.079 (13)	0.059 (10)	0.013 (9)	−0.012 (9)	−0.017 (10)
C10	0.060 (10)	0.060 (10)	0.066 (11)	−0.002 (8)	−0.018 (9)	0.009 (9)

Geometric parameters (Å, º) top

I1—C6	2.113 (12)	C2—H2B	0.9300
S—O2	1.429 (11)	C3—C4	1.36 (2)
S—O3	1.441 (10)	C4—C5	1.413 (18)
S—O1	1.449 (12)	C4—H4A	0.9300
S—C3	1.796 (12)	C5—C6	1.404 (18)
O1W—H1WA	0.88 (9)	C5—H5A	0.9300
O1W—H1WB	0.94 (9)	C7—H7A	0.9600
O2—H2A	0.8500	C7—H7B	0.9600
O4—C10	1.30 (2)	C7—H7C	0.9600
N1—C10	1.30 (2)	C8—H8A	0.9600
N1—C7	1.44 (2)	C8—H8B	0.9600
N1—C8	1.51 (2)	C8—H8C	0.9600
C1—C6	1.363 (19)	C9—C10	1.50 (2)
C1—C2	1.386 (17)	C9—H9A	0.9600
C1—H1B	0.9300	C9—H9B	0.9600
C2—C3	1.354 (17)	C9—H9C	0.9600

O2—S—O3	111.4 (8)	C4—C5—H5A	121.3
O2—S—O1	114.4 (9)	C1—C6—C5	122.7 (12)
O3—S—O1	112.0 (7)	C1—C6—I1	120.8 (9)
O2—S—C3	105.5 (6)	C5—C6—I1	116.4 (9)
O3—S—C3	105.3 (6)	N1—C7—H7A	109.5
O1—S—C3	107.5 (7)	N1—C7—H7B	109.5
H1WA—O1W—H1WB	125 (10)	H7A—C7—H7B	109.5
S—O2—H2A	109.0	N1—C7—H7C	109.5
C10—N1—C7	123.8 (18)	H7A—C7—H7C	109.5
C10—N1—C8	118.8 (16)	H7B—C7—H7C	109.5
C7—N1—C8	117.5 (17)	N1—C8—H8A	109.5
C6—C1—C2	117.6 (12)	N1—C8—H8B	109.5
C6—C1—H1B	121.2	H8A—C8—H8B	109.5
C2—C1—H1B	121.2	N1—C8—H8C	109.5
C3—C2—C1	121.2 (13)	H8A—C8—H8C	109.5
C3—C2—H2B	119.4	H8B—C8—H8C	109.5
C1—C2—H2B	119.4	C10—C9—H9A	109.5
C2—C3—C4	122.1 (12)	C10—C9—H9B	109.5
C2—C3—S	120.2 (11)	H9A—C9—H9B	109.5
C4—C3—S	117.7 (9)	C10—C9—H9C	109.5
C3—C4—C5	118.9 (11)	H9A—C9—H9C	109.5
C3—C4—H4A	120.5	H9B—C9—H9C	109.5
C5—C4—H4A	120.5	O4—C10—N1	118.1 (16)
C6—C5—C4	117.5 (13)	O4—C10—C9	120.3 (16)
C6—C5—H5A	121.3	N1—C10—C9	121.7 (19)

C6—C1—C2—C3	1 (2)	S—C3—C4—C5	179.4 (8)
C1—C2—C3—C4	0 (2)	C3—C4—C5—C6	−1.2 (17)
C1—C2—C3—S	−179.4 (10)	C2—C1—C6—C5	−2 (2)
O2—S—C3—C2	114.1 (12)	C2—C1—C6—I1	180.0 (9)
O3—S—C3—C2	−127.9 (11)	C4—C5—C6—C1	2.3 (18)
O1—S—C3—C2	−8.3 (13)	C4—C5—C6—I1	−179.9 (8)
O2—S—C3—C4	−65.0 (13)	C7—N1—C10—O4	178.7 (14)
O3—S—C3—C4	52.9 (11)	C8—N1—C10—O4	−1 (2)
O1—S—C3—C4	172.5 (10)	C7—N1—C10—C9	−3 (3)
C2—C3—C4—C5	0.3 (19)	C8—N1—C10—C9	176.9 (14)

Hydrogen-bond geometry (Å, º) top

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
C2—H2B···O1	0.93	2.52	2.925 (17)	106
C5—H5A···O1^v	0.93	2.55	3.192 (17)	126
C8—H8A···O4	0.96	2.21	2.64 (2)	106
C9—H9A···O3	0.96	2.56	3.48 (2)	161

Symmetry codes: (i) x+1/2, −y+1, z−1; (ii) x+1, y−1, z−1; (iii) −x+1/2, y+1, z+1/2; (iv) x, y−1, z; (v) −x+1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₆H₅IO₃S·C₄H₉NO·H₂O
M_r	389.21
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	294
a, b, c (Å)	14.173 (3), 7.7480 (15), 13.272 (3)
V (Å³)	1457.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.35
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.539, 0.799
No. of measured, independent and observed [I > 2σ(I)] reflections	1490, 1490, 1096
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.162, 1.07
No. of reflections	1490
No. of parameters	172
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.53, −2.42
Absolute structure	Flack (1983), 7 Friedel pairs
Absolute structure parameter	0.13 (10)

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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	0.8500	2.5700	3.208 (16)	133.00
C1—H1B···O3^iv	0.9300	2.4600	3.378 (15)	168.00
C2—H2B···O1	0.9300	2.5200	2.925 (17)	106.00
C5—H5A···O1^v	0.9300	2.5500	3.192 (17)	126.00
C8—H8A···O4	0.9600	2.2100	2.64 (2)	106.00
C9—H9A···O3	0.9600	2.5600	3.48 (2)	161.00

Symmetry codes: (i) x+1/2, −y+1, z−1; (ii) x+1, y−1, z−1; (iii) −x+1/2, y+1, z+1/2; (iv) x, y−1, z; (v) −x+1/2, y, z−1/2.

Acknowledgements

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

References

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