3-(2-Methyl-1,3-benzo­thia­zol-3-ium-3-yl)propane-1-sulfonate monohydrate

Zhang, G.-C.; Kong, M.; Li, S.-L.

doi:10.1107/S1600536814011660

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o714

doi:10.1107/S1600536814011660

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3-(2-Methyl-1,3-benzothiazol-3-ium-3-yl)propane-1-sulfonate monohydrate

Guo-Cui Zhang,^a Ming Kong ^a and Sheng-Li Li ^a ^*

^aDeparment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, Key Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: lsl1968@ahu.edu.cn

Edited by S. Parkin, University of Kentucky, USA (Received 7 May 2014; accepted 20 May 2014; online 24 May 2014)

In the title hydrated zwitterion, C₁₁H₁₃NO₃S₂·H₂O, the N—C—C—C and C—C—C—S torsion angles in the side-chain are 171.06 (14) and 173.73 (12)°, respectively. In the crystal, inversion-related molecules are π-stacked with an interplanar separation of 3.3847 (2) Å. O—H⋯O hydrogen bonds link inversion-related molecules with a pair of water molecules to form R₄²(8) rings. The closest S⋯S contact is 3.4051 (15) Å between inversion-related molecules.

CCDC reference: 1004303

Related literature

The crystal structure of a related benzothiazole derivative is described by Lynch (2002 ). An analysis of bond angles in the thiazole ring system has been given by Muir et al. (1987 ). Applications of benzothiazole derivatives have been described by Vicini et al. (2003 ); Bondock et al. (2010 ); Paramashivappa et al. (2003 ) and Sayama et al. (2002 ).

Experimental

Crystal data

C₁₁H₁₃NO₃S₂·H₂O
M_r = 289.36
Monoclinic, P 2₁ /c
a = 10.936 (5) Å
b = 8.708 (5) Å
c = 13.794 (5) Å
β = 109.529 (5)°
V = 1238.0 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.880, T_max = 0.919
8500 measured reflections
2182 independent reflections
2105 reflections with I > 2sσ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.080
S = 1.01
2182 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H11⋯O3ⁱ	0.76	2.07	2.831 (2)	176
O4—H12⋯O3	0.82	2.21	2.994 (3)	160
C3—H3A⋯O1ⁱⁱ	0.97	2.39	3.269 (3)	151
C4—H4C⋯O4ⁱⁱⁱ	0.96	2.54	3.487 (3)	169
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1004303

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536814011660/pk2524sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814011660/pk2524Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814011660/pk2524Isup3.cml

checkCIF report

Comment top

Benzothiazole, a small and simple heterocyclic molecule, has raised considerable interest. It can be used to synthesize some Schiff bases (Vicini et al., 2003), and other derivatives that are antimicrobial (Bondock et al., 2010) and bioactive (Paramashivappa et al., 2003). They have also been used in dye-sensitized solar cells (Sayama et al., 2002). Spurred by this, we synthesized 3-(2-methylbenzo[d]thiazol-3-ium-3-yl)propane-1-sulfonate (Fig. 1), which contains a sulfonic group, with the aim of increased solubility. The single-crystal structure contains one water molecule. Comparing with C₇H₅N₃O₂S₁·H₂O (Lynch, 2002), both of them are in a hydrogen-bonding network with water molecules. The water H atoms are connected with O atoms of sulfonic moieties and the molecules are interconnected, via hydrogen bonds (Table 1) [O4—H11···O3ⁱ, symmetry codes: (i) -x, -y + 1, -z + 1; C3—H3A···O1ⁱⁱ, symmetry codes: (ii) -x, y + 1/2, -z + 3/2; C4—H4C···O4ⁱⁱⁱ, symmetry codes: (iii) -x, y - 1/2, -z + 3/2]. There is a R²₄(8) ring formed by hydrogen-bonded water to O3—S1 interactions. Two characteristic O4—H12···O3 and O4—H11···O3ⁱ distances are 2.994 (3) Å and 2.831 (2) Å, respectively (Fig.2). In the crystal, inversion related (1-x,1-y,2-z) molecules are π-stacked with an interplanar separation of 3.3847 (2) Å. O—H···O hydrogen bonds link inversion-related (-x,1-y,1-z) molecules with a pair of water molecules to form R²₄(8) rings. The closest ring S···S contact is 3.4051 (15) Å between inversion-related (1-x,-y,2-z) molecules (Fig.3). The bond length between N1 and C5 [1.3216 (2) Å] indicates some double bond character and is conjugated with neighbouring bonds. The two distances of S2—C6 and S2—C5 are nearly the same [1.7327 (19) Å and 1.7024 (18) Å, respectively]. In addition, the large size of the S atom compared with N results in a reduction of the C5—S2—C6 angle [91.069 (8)°] compared with the C5—N1—C11 angle [114.001 (14)°] in thiazole ring. This reveals that the S atom might be using unhybridized p-orbitals for bonding (Muir et al., 1987).

Related literature top

The crystal structure of a related benzothiazole derivative is described by Lynch (2002). An analysis of bond angles in the thiazole ring system has been given by Muir et al. (1987). Applications of benzothiazole derivatives have been described by Vicini et al. (2003); Bondock et al. (2010); Paramashivappa et al. (2003) and Sayama et al. (2002).

Experimental top

The title complex, 3-(2-methylbenzo[d]thiazol-3-ium-3-yl)propane-1-sulfonate, was prepared by mixing 2-methylbenzo[d]thiazole (1.49 g, 0.010 mol) with 1,2-oxathiolane 2,2-dioxide (1.47 g, 0.012 mol) in toluene (20 ml). The mixture was heated to reflux for 4 h. After the reaction was complete, the solution was cooled to room temperature. The mixture was filtered and washed with ethanol 3 times to give a white solid. Colorless block-shaped crystals were grown by slow evaporation an acetonitrile/ethanol mixture. ¹H NMR: (400 Hz, DMSO-d₆), d(p.p.m.): 8.43 (t, 2H), 7.90 (t, 1H), 7.80 (t, 1H), 4.90 (t, 2H), 3.20 (s, 3H), 2.65 (t, 2H), 2.15 (q, 2H).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : The molecular structure of the title compound showing 30% probability displacement ellipsoids.
	Fig. 2. : View of the R²₄(8) ring formed by O4—H12···O3 and O4—H11···O3ⁱ intermolecular interactions, showing O—H···O hydrogen-bonding interactions as dashed lines.
	Fig. 3. : Packing diagram of the title compound.

3-(2-Methyl-1,3-benzothiazol-3-ium-3-yl)propane-1-sulfonate monohydrate top

Crystal data top

C₁₁H₁₃NO₃S₂·H₂O	F(000) = 608
M_r = 289.36	D_x = 1.552 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 7517 reflections
a = 10.936 (5) Å	θ = 2.8–27.1°
b = 8.708 (5) Å	µ = 0.44 mm⁻¹
c = 13.794 (5) Å	T = 296 K
β = 109.529 (5)°	Block, white
V = 1238.0 (10) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2182 independent reflections
Radiation source: fine-focus sealed tube	2105 reflections with I > 2sσ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→12
T_min = 0.880, T_max = 0.919	k = −10→10
8500 measured reflections	l = −16→16

Refinement top

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) = 0.080	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0449P)² + 0.799P] where P = (F_o² + 2F_c²)/3
2182 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₁H₁₃NO₃S₂·H₂O	V = 1238.0 (10) Å³
M_r = 289.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.936 (5) Å	µ = 0.44 mm⁻¹
b = 8.708 (5) Å	T = 296 K
c = 13.794 (5) Å	0.30 × 0.20 × 0.20 mm
β = 109.529 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2182 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2105 reflections with I > 2sσ(I)
T_min = 0.880, T_max = 0.919	R_int = 0.016
8500 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.01	Δρ_max = 0.31 e Å⁻³
2182 reflections	Δρ_min = −0.42 e Å⁻³
164 parameters

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
C1	−0.04082 (15)	0.49554 (19)	0.80688 (12)	0.0271 (3)
H1A	−0.0210	0.6044	0.8110	0.033*
H1B	−0.0771	0.4720	0.8604	0.033*
C2	0.08437 (15)	0.4060 (2)	0.82760 (12)	0.0294 (4)
H2A	0.1180	0.4207	0.7715	0.035*
H2B	0.0682	0.2972	0.8327	0.035*
C3	0.18249 (16)	0.46262 (19)	0.92775 (13)	0.0301 (4)
H3A	0.2076	0.5670	0.9186	0.036*
H3B	0.1426	0.4636	0.9809	0.036*
C4	0.23671 (18)	0.2245 (2)	1.09534 (14)	0.0388 (4)
H4A	0.2531	0.2983	1.1499	0.058*
H4B	0.2549	0.1232	1.1240	0.058*
H4C	0.1474	0.2306	1.0522	0.058*
C5	0.32123 (15)	0.25761 (19)	1.03338 (12)	0.0272 (3)
C6	0.49490 (15)	0.26655 (18)	0.95809 (12)	0.0264 (3)
C7	0.60073 (16)	0.2548 (2)	0.92365 (13)	0.0333 (4)
H7	0.6661	0.1832	0.9517	0.040*
C8	0.60501 (18)	0.3533 (2)	0.84639 (14)	0.0390 (4)
H8	0.6733	0.3465	0.8207	0.047*
C9	0.50797 (19)	0.4631 (2)	0.80639 (13)	0.0383 (4)
H9	0.5145	0.5296	0.7556	0.046*
C10	0.40270 (17)	0.4758 (2)	0.83992 (13)	0.0328 (4)
H10	0.3387	0.5494	0.8131	0.039*
C11	0.39668 (15)	0.37330 (18)	0.91581 (12)	0.0258 (3)
N1	0.29980 (13)	0.36398 (15)	0.96126 (10)	0.0257 (3)
O1	−0.18774 (14)	0.29348 (16)	0.68281 (11)	0.0490 (4)
O2	−0.26970 (12)	0.55228 (16)	0.68129 (11)	0.0447 (3)
O3	−0.10098 (14)	0.50116 (19)	0.60890 (10)	0.0487 (4)
O4	0.09084 (19)	0.6948 (3)	0.55198 (17)	0.0951 (8)
H11	0.0932	0.6459	0.5068	0.143*
H12	0.0523	0.6424	0.5819	0.143*
S1	−0.15982 (4)	0.45636 (5)	0.68522 (3)	0.02836 (14)
S2	0.46338 (4)	0.16183 (5)	1.05392 (3)	0.02926 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0260 (8)	0.0278 (8)	0.0252 (8)	0.0026 (7)	0.0053 (6)	−0.0020 (6)
C2	0.0262 (8)	0.0304 (8)	0.0289 (8)	0.0044 (7)	0.0058 (7)	−0.0041 (7)
C3	0.0282 (8)	0.0283 (8)	0.0295 (8)	0.0087 (7)	0.0039 (7)	−0.0034 (6)
C4	0.0365 (9)	0.0464 (11)	0.0353 (9)	0.0047 (8)	0.0144 (8)	0.0022 (8)
C5	0.0269 (8)	0.0271 (8)	0.0238 (7)	0.0020 (6)	0.0035 (6)	−0.0043 (6)
C6	0.0265 (8)	0.0243 (8)	0.0254 (8)	−0.0021 (6)	0.0049 (6)	−0.0043 (6)
C7	0.0266 (8)	0.0352 (9)	0.0368 (9)	−0.0014 (7)	0.0089 (7)	−0.0075 (7)
C8	0.0353 (10)	0.0461 (11)	0.0382 (10)	−0.0124 (8)	0.0156 (8)	−0.0107 (8)
C9	0.0457 (11)	0.0394 (10)	0.0283 (9)	−0.0146 (8)	0.0102 (8)	−0.0020 (7)
C10	0.0351 (9)	0.0292 (9)	0.0269 (8)	−0.0042 (7)	0.0010 (7)	0.0001 (7)
C11	0.0253 (8)	0.0245 (8)	0.0244 (7)	−0.0025 (6)	0.0039 (6)	−0.0052 (6)
N1	0.0247 (7)	0.0250 (7)	0.0243 (6)	0.0036 (5)	0.0038 (5)	−0.0029 (5)
O1	0.0500 (8)	0.0333 (7)	0.0562 (9)	−0.0105 (6)	0.0079 (7)	−0.0086 (6)
O2	0.0295 (7)	0.0515 (8)	0.0460 (8)	0.0109 (6)	0.0032 (6)	0.0044 (6)
O3	0.0504 (8)	0.0678 (10)	0.0303 (7)	−0.0090 (7)	0.0166 (6)	0.0000 (6)
O4	0.0798 (13)	0.1204 (18)	0.1083 (16)	−0.0428 (13)	0.0622 (12)	−0.0642 (14)
S1	0.0254 (2)	0.0311 (2)	0.0257 (2)	−0.00197 (15)	0.00465 (17)	−0.00040 (15)
S2	0.0295 (2)	0.0272 (2)	0.0296 (2)	0.00697 (16)	0.00785 (17)	0.00262 (16)

Geometric parameters (Å, º) top

C1—C2	1.518 (2)	C6—C7	1.394 (2)
C1—S1	1.7793 (16)	C6—S2	1.7329 (17)
C1—H1A	0.9700	C7—C8	1.381 (3)
C1—H1B	0.9700	C7—H7	0.9300
C2—C3	1.521 (2)	C8—C9	1.397 (3)
C2—H2A	0.9700	C8—H8	0.9300
C2—H2B	0.9700	C9—C10	1.381 (3)
C3—N1	1.484 (2)	C9—H9	0.9300
C3—H3A	0.9700	C10—C11	1.394 (2)
C3—H3B	0.9700	C10—H10	0.9300
C4—C5	1.482 (2)	C11—N1	1.402 (2)
C4—H4A	0.9600	O1—S1	1.4489 (16)
C4—H4B	0.9600	O2—S1	1.4495 (14)
C4—H4C	0.9600	O3—S1	1.4587 (14)
C5—N1	1.322 (2)	O4—H11	0.7630
C5—S2	1.7024 (17)	O4—H12	0.8203
C6—C11	1.393 (2)

C2—C1—S1	114.11 (11)	C11—C6—S2	110.39 (12)
C2—C1—H1A	108.7	C7—C6—S2	128.39 (13)
S1—C1—H1A	108.7	C8—C7—C6	117.63 (17)
C2—C1—H1B	108.7	C8—C7—H7	121.2
S1—C1—H1B	108.7	C6—C7—H7	121.2
H1A—C1—H1B	107.6	C7—C8—C9	120.82 (17)
C1—C2—C3	108.81 (13)	C7—C8—H8	119.6
C1—C2—H2A	109.9	C9—C8—H8	119.6
C3—C2—H2A	109.9	C10—C9—C8	122.04 (17)
C1—C2—H2B	109.9	C10—C9—H9	119.0
C3—C2—H2B	109.9	C8—C9—H9	119.0
H2A—C2—H2B	108.3	C9—C10—C11	117.02 (16)
N1—C3—C2	111.67 (13)	C9—C10—H10	121.5
N1—C3—H3A	109.3	C11—C10—H10	121.5
C2—C3—H3A	109.3	C6—C11—C10	121.23 (16)
N1—C3—H3B	109.3	C6—C11—N1	111.50 (14)
C2—C3—H3B	109.3	C10—C11—N1	127.25 (15)
H3A—C3—H3B	107.9	C5—N1—C11	114.00 (13)
C5—C4—H4A	109.5	C5—N1—C3	123.89 (14)
C5—C4—H4B	109.5	C11—N1—C3	122.08 (13)
H4A—C4—H4B	109.5	H11—O4—H12	105.3
C5—C4—H4C	109.5	O1—S1—O2	113.43 (9)
H4A—C4—H4C	109.5	O1—S1—O3	112.69 (9)
H4B—C4—H4C	109.5	O2—S1—O3	112.28 (9)
N1—C5—C4	125.63 (15)	O1—S1—C1	106.94 (8)
N1—C5—S2	113.01 (12)	O2—S1—C1	105.11 (8)
C4—C5—S2	121.31 (13)	O3—S1—C1	105.63 (9)
C11—C6—C7	121.22 (16)	C5—S2—C6	91.07 (8)

S1—C1—C2—C3	173.73 (12)	C4—C5—N1—C3	−3.1 (2)
C1—C2—C3—N1	171.06 (14)	S2—C5—N1—C3	179.33 (11)
C11—C6—C7—C8	0.3 (2)	C6—C11—N1—C5	−0.11 (19)
S2—C6—C7—C8	−179.16 (13)	C10—C11—N1—C5	−178.36 (15)
C6—C7—C8—C9	1.6 (3)	C6—C11—N1—C3	−178.26 (13)
C7—C8—C9—C10	−1.6 (3)	C10—C11—N1—C3	3.5 (2)
C8—C9—C10—C11	−0.2 (2)	C2—C3—N1—C5	−100.77 (18)
C7—C6—C11—C10	−2.2 (2)	C2—C3—N1—C11	77.20 (19)
S2—C6—C11—C10	177.37 (12)	C2—C1—S1—O1	59.13 (15)
C7—C6—C11—N1	179.47 (14)	C2—C1—S1—O2	179.98 (13)
S2—C6—C11—N1	−1.01 (16)	C2—C1—S1—O3	−61.12 (15)
C9—C10—C11—C6	2.1 (2)	N1—C5—S2—C6	−1.51 (12)
C9—C10—C11—N1	−179.81 (15)	C4—C5—S2—C6	−179.18 (14)
C4—C5—N1—C11	178.76 (15)	C11—C6—S2—C5	1.41 (12)
S2—C5—N1—C11	1.21 (17)	C7—C6—S2—C5	−179.11 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H11···O3ⁱ	0.76	2.07	2.831 (2)	176
O4—H12···O3	0.82	2.21	2.994 (3)	160
C3—H3A···O1ⁱⁱ	0.97	2.39	3.269 (3)	151
C4—H4C···O4ⁱⁱⁱ	0.96	2.54	3.487 (3)	169

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y+1/2, −z+3/2; (iii) −x, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H11···O3ⁱ	0.76	2.07	2.831 (2)	175.7
O4—H12···O3	0.82	2.21	2.994 (3)	160.3
C3—H3A···O1ⁱⁱ	0.97	2.39	3.269 (3)	151.3
C4—H4C···O4ⁱⁱⁱ	0.96	2.54	3.487 (3)	169.3

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y+1/2, −z+3/2; (iii) −x, y−1/2, −z+3/2.

Acknowledgements

This work was supported by the Anhui Provincial Natural Science Foundation (1308085MB24) and the Educational Commission of Anhui Province of China (KJ2012A025).

References

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