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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1640.
Published online 2009 June 20. doi:  10.1107/S160053680902248X
PMCID: PMC2969305

Tris(2-hydroxy­ethyl)ammonium 1,3-benzo­thia­zole-2-thiol­ate

Abstract

In the title compound, C6H16NO3 +·C7H4NS2 , the cations and anions are connected by O—H(...)N and O—H(...)S hydrogen bonding. Weak C—H(...)O hydrogen bonding between adjacent cations helps to stabilize the crystal structure.

Related literature

For related structures, see Bethge et al. (2008 [triangle]); Siracusa et al. (2008 [triangle]); Solar et al. (2008 [triangle]); Varlamov et al. (2005 [triangle]).

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Object name is e-65-o1640-scheme1.jpg

Experimental

Crystal data

  • C6H16NO3 +·C7H4NS2
  • M r = 316.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1640-efi1.jpg
  • a = 16.496 (2) Å
  • b = 5.7184 (8) Å
  • c = 17.462 (3) Å
  • β = 111.524 (2)°
  • V = 1532.3 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.36 mm−1
  • T = 296 K
  • 0.56 × 0.38 × 0.23 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.803, T max = 0.921
  • 7572 measured reflections
  • 2827 independent reflections
  • 2185 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.092
  • S = 1.04
  • 2827 reflections
  • 185 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902248X/xu2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902248X/xu2531Isup2.hkl

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

Acknowledgments

The work was supported by the National Natural Science Foundation of China (No. 20772037) and the NSF of Guangdong Province, China (No. 06025033).

supplementary crystallographic information

Comment

Some related compounds involving the 2-mercaptobenzothiazole and its derivatives has reported previously (Varlamov et al., 2005; Solar et al., 2008; Siracusa et al. 2008; Bethge et al., 2008). The crystal structure of the title compound consists of tris(2-hydroxyethyl)ammonium cations and benzothiazole-2-thiolate anions (Fig. 1). The cations and anions are connected by O—H···N and O—H···S hydrogen bonding (Table 1).

Experimental

A mixture of benzothiazole (335 mg, 2 mmol), triethanolamine (0.4 ml and 3 mmol) in ethyl acetate (20 ml) was refluxed for 20 h. The resultant yellow solution was delaminated into two layers at room temperature and then filtered. Single crystals suitable for X-ray diffraction were obtained in two day by slow diffusion of diethyl ether into a dilute solution of the title complex in ethyl acetate. The elemental analysis; calculated for C13H20N2O3S2: C 49.37, H 6.33, N 8.86%; found: C 49.31, H 6.38, N 8.82%.

Refinement

H atoms were placed in idealized positions with C—H = 0.93 or 0.97 Å, O—H = 0.82 Å, N—H = 0.91 Å, and refined in riding-model approximation. Uiso(H) = 1.5Ueq(O) and 1.2Ueq(N,C).

Figures

Fig. 1.
The structure of the title compound with 50% probability displacement ellipsoids.

Crystal data

C6H16NO3+·C7H4NS2F(000) = 672
Mr = 316.43Dx = 1.372 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 236 reflections
a = 16.496 (2) Åθ = 2.4–25.5°
b = 5.7184 (8) ŵ = 0.36 mm1
c = 17.462 (3) ÅT = 296 K
β = 111.524 (2)°Block, colorless
V = 1532.3 (4) Å30.56 × 0.38 × 0.23 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer2827 independent reflections
Radiation source: fine-focus sealed tube2185 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −19→19
Tmin = 0.803, Tmax = 0.921k = −6→6
7572 measured reflectionsl = −20→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0394P)2 + 0.2793P] where P = (Fo2 + 2Fc2)/3
2827 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.16 e Å3

Special details

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)

xyzUiso*/Ueq
C10.26675 (13)1.1324 (4)0.12815 (11)0.0361 (5)
C20.39268 (13)0.8624 (4)0.15930 (11)0.0347 (5)
C30.39516 (12)1.0658 (3)0.11586 (11)0.0347 (5)
C40.46629 (14)1.1048 (4)0.09259 (13)0.0459 (5)
H40.46921.23820.06320.055*
C50.53229 (15)0.9413 (5)0.11398 (14)0.0521 (6)
H50.58030.96670.09920.062*
C60.52890 (15)0.7410 (4)0.15671 (13)0.0498 (6)
H60.57430.63350.16990.060*
C70.45902 (14)0.6983 (4)0.18000 (12)0.0445 (5)
H70.45650.56340.20880.053*
C80.25776 (13)0.6974 (4)0.44442 (12)0.0412 (5)
H8A0.28200.54720.43830.049*
H8B0.25410.70250.49860.049*
C90.31648 (14)0.8890 (4)0.43727 (13)0.0451 (5)
H9A0.37260.87600.48190.054*
H9B0.32570.87270.38580.054*
C100.09961 (15)0.6154 (4)0.40603 (14)0.0501 (6)
H10A0.11750.45930.42720.060*
H10B0.04580.60190.35850.060*
C110.08354 (14)0.7592 (4)0.47092 (14)0.0485 (6)
H11A0.03230.70220.47980.058*
H11B0.13300.74790.52240.058*
C120.16366 (15)0.6302 (4)0.29797 (12)0.0477 (6)
H12A0.15240.46330.29510.057*
H12B0.21900.65560.29160.057*
C130.09228 (15)0.7522 (5)0.22968 (13)0.0537 (6)
H13A0.09690.71550.17720.064*
H13B0.03590.69840.22820.064*
N10.32350 (11)1.2134 (3)0.09787 (10)0.0371 (4)
N20.16844 (9)0.7219 (3)0.38008 (9)0.0318 (4)
H2A0.15690.87780.37360.038*
O10.28024 (11)1.1097 (3)0.44019 (9)0.0515 (4)
H10.28981.14490.48820.077*
O20.07100 (11)0.9936 (3)0.44415 (9)0.0581 (4)
H20.09271.08080.48370.087*
O30.09930 (10)0.9968 (3)0.24292 (9)0.0533 (4)
H30.12441.05510.21480.080*
S10.29720 (3)0.86166 (10)0.17920 (3)0.04177 (18)
S20.16918 (4)1.25406 (11)0.11908 (4)0.04881 (19)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0443 (12)0.0320 (12)0.0297 (10)−0.0048 (9)0.0107 (9)−0.0028 (9)
C20.0382 (11)0.0340 (12)0.0270 (9)−0.0052 (9)0.0063 (8)−0.0007 (9)
C30.0405 (11)0.0326 (11)0.0289 (9)−0.0054 (9)0.0103 (8)−0.0021 (9)
C40.0496 (13)0.0463 (15)0.0453 (12)−0.0018 (11)0.0215 (10)0.0073 (11)
C50.0451 (13)0.0620 (17)0.0543 (14)−0.0008 (11)0.0245 (11)−0.0012 (12)
C60.0465 (13)0.0513 (16)0.0478 (13)0.0115 (11)0.0128 (11)−0.0004 (11)
C70.0509 (13)0.0388 (13)0.0379 (11)0.0017 (10)0.0094 (10)0.0031 (10)
C80.0392 (12)0.0404 (13)0.0411 (11)0.0054 (9)0.0114 (9)0.0034 (10)
C90.0449 (12)0.0458 (14)0.0457 (12)−0.0063 (10)0.0181 (10)−0.0091 (11)
C100.0506 (13)0.0500 (15)0.0526 (13)−0.0124 (11)0.0225 (11)−0.0010 (11)
C110.0449 (13)0.0574 (16)0.0485 (13)−0.0021 (11)0.0234 (11)0.0049 (12)
C120.0649 (15)0.0422 (14)0.0375 (11)0.0001 (11)0.0204 (11)−0.0070 (10)
C130.0533 (14)0.0671 (18)0.0342 (11)−0.0093 (12)0.0082 (10)0.0001 (11)
N10.0436 (10)0.0307 (10)0.0375 (9)−0.0019 (8)0.0154 (8)0.0030 (7)
N20.0351 (9)0.0275 (9)0.0319 (8)0.0001 (7)0.0110 (7)0.0011 (7)
O10.0690 (10)0.0380 (10)0.0454 (8)−0.0041 (8)0.0186 (8)−0.0074 (7)
O20.0705 (11)0.0570 (12)0.0490 (9)0.0164 (9)0.0244 (8)0.0038 (8)
O30.0591 (10)0.0590 (12)0.0462 (9)0.0122 (8)0.0244 (7)0.0144 (8)
S10.0457 (3)0.0401 (3)0.0402 (3)−0.0032 (2)0.0166 (2)0.0092 (2)
S20.0518 (4)0.0470 (4)0.0536 (4)0.0074 (3)0.0263 (3)0.0074 (3)

Geometric parameters (Å, °)

C1—N11.317 (2)C9—H9A0.9700
C1—S21.707 (2)C9—H9B0.9700
C1—S11.765 (2)C10—N21.497 (2)
C2—C71.385 (3)C10—C111.500 (3)
C2—C31.398 (3)C10—H10A0.9700
C2—S11.733 (2)C10—H10B0.9700
C3—N11.391 (2)C11—O21.410 (3)
C3—C41.393 (3)C11—H11A0.9700
C4—C51.379 (3)C11—H11B0.9700
C4—H40.9300C12—N21.501 (2)
C5—C61.379 (3)C12—C131.505 (3)
C5—H50.9300C12—H12A0.9700
C6—C71.378 (3)C12—H12B0.9700
C6—H60.9300C13—O31.415 (3)
C7—H70.9300C13—H13A0.9700
C8—N21.496 (2)C13—H13B0.9700
C8—C91.497 (3)N2—H2A0.9100
C8—H8A0.9700O1—H10.8200
C8—H8B0.9700O2—H20.8200
C9—O11.405 (3)O3—H30.8200
N1—C1—S2127.19 (16)N2—C10—H10A109.3
N1—C1—S1113.51 (15)C11—C10—H10A109.3
S2—C1—S1119.24 (11)N2—C10—H10B109.3
C7—C2—C3121.86 (19)C11—C10—H10B109.3
C7—C2—S1129.44 (16)H10A—C10—H10B107.9
C3—C2—S1108.70 (15)O2—C11—C10108.40 (17)
N1—C3—C4125.02 (18)O2—C11—H11A110.0
N1—C3—C2115.84 (17)C10—C11—H11A110.0
C4—C3—C2119.13 (19)O2—C11—H11B110.0
C5—C4—C3118.6 (2)C10—C11—H11B110.0
C5—C4—H4120.7H11A—C11—H11B108.4
C3—C4—H4120.7N2—C12—C13110.28 (18)
C4—C5—C6121.7 (2)N2—C12—H12A109.6
C4—C5—H5119.2C13—C12—H12A109.6
C6—C5—H5119.2N2—C12—H12B109.6
C7—C6—C5120.7 (2)C13—C12—H12B109.6
C7—C6—H6119.6H12A—C12—H12B108.1
C5—C6—H6119.6O3—C13—C12109.59 (18)
C6—C7—C2118.0 (2)O3—C13—H13A109.8
C6—C7—H7121.0C12—C13—H13A109.8
C2—C7—H7121.0O3—C13—H13B109.8
N2—C8—C9110.98 (17)C12—C13—H13B109.8
N2—C8—H8A109.4H13A—C13—H13B108.2
C9—C8—H8A109.4C1—N1—C3111.49 (17)
N2—C8—H8B109.4C8—N2—C10112.46 (15)
C9—C8—H8B109.4C8—N2—C12112.13 (15)
H8A—C8—H8B108.0C10—N2—C12111.54 (16)
O1—C9—C8110.92 (17)C8—N2—H2A106.8
O1—C9—H9A109.5C10—N2—H2A106.8
C8—C9—H9A109.5C12—N2—H2A106.8
O1—C9—H9B109.5C9—O1—H1109.5
C8—C9—H9B109.5C11—O2—H2109.5
H9A—C9—H9B108.0C13—O3—H3109.5
N2—C10—C11111.68 (18)C2—S1—C190.44 (9)
C7—C2—C3—N1178.88 (18)S2—C1—N1—C3−178.71 (15)
S1—C2—C3—N1−1.0 (2)S1—C1—N1—C3−1.5 (2)
C7—C2—C3—C40.1 (3)C4—C3—N1—C1−179.62 (19)
S1—C2—C3—C4−179.79 (15)C2—C3—N1—C11.7 (2)
N1—C3—C4—C5−179.2 (2)C9—C8—N2—C10−153.34 (17)
C2—C3—C4—C5−0.5 (3)C9—C8—N2—C1280.0 (2)
C3—C4—C5—C60.7 (3)C11—C10—N2—C872.5 (2)
C4—C5—C6—C7−0.4 (3)C11—C10—N2—C12−160.57 (18)
C5—C6—C7—C2−0.1 (3)C13—C12—N2—C8−153.34 (18)
C3—C2—C7—C60.2 (3)C13—C12—N2—C1079.5 (2)
S1—C2—C7—C6−179.94 (16)C7—C2—S1—C1−179.76 (19)
N2—C8—C9—O155.1 (2)C3—C2—S1—C10.09 (14)
N2—C10—C11—O249.9 (2)N1—C1—S1—C20.85 (15)
N2—C12—C13—O348.2 (2)S2—C1—S1—C2178.27 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.821.962.770 (2)168
O2—H2···S2i0.822.433.2258 (17)165
O3—H3···S20.822.353.1621 (16)169
C8—H8A···O1ii0.972.503.385 (3)151
C10—H10B···O3iii0.972.473.425 (3)167

Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2531).

References

  • Bethge, L., Jarikote, D. V. & Seitz, O. (2008). Bioorg. Med. Chem. 16, 114–125. [PubMed]
  • Bruker (1998). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siracusa, M. A., Salerno, L., Modica, M. N., Pittala, V., Romeo, G., Amato, M. E., Nowak, M., Bojarski, A. J., Mereghetti, I., Cagnotto, A. & Mennini, T. (2008). J. Med. Chem.51, 4529–4538. [PubMed]
  • Solar, M., del Ghosh, A. K. & Zajc, B. (2008). J. Org. Chem.73, 8206–8211. [PMC free article] [PubMed]
  • Varlamov, V. T., Ferreri, C. & Chatgilialoglu, C. (2005). J. Organomet. Chem.690, 1756–1762.

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