4-(4-Diethyl­amino-2-hydroxy­benzyl­idene­ammonio)-3-methyl­benzene­sulfonate dihydrate

Zhang, W.; Chen, Y.-T.

doi:10.1107/S1600536809035090

Volume 65
Part 10
Page o2339
October 2009

Received 27 August 2009
Accepted 1 September 2009
Online 5 September 2009

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.004 Å
R = 0.054
wR = 0.171
Data-to-parameter ratio = 13.7
Details

4-(4-Diethylamino-2-hydroxybenzylideneammonio)-3-methylbenzenesulfonate dihydrate

Wei Zhang ^a and Yuan-Tao Chen ^a ^*

^aDepartment of Chemistry, Qinghai Normal University, Xining 810008, People's Republic of China
Correspondence e-mail: chenyt@qhnu.edu.cn

In the crystal of the title compound, C₁₈H₂₂N₂O₄S·2H₂O, molecules are linked into a one-dimensional chain structure by C-HO, N-HO, O-HO and O-HN hydrogen bonds.

Related literature

For the biological and pharmacological activities of Schiff base compounds, see: Bu et al. (2001); Ranford et al. (1998).

Experimental

Crystal data

C₁₈H₂₂N₂O₄S·2H₂O
M_r = 398.47
Monoclinic, C 2/c
a = 21.690 (3) Å
b = 11.4142 (17) Å
c = 16.639 (2) Å
= 112.459 (2)°
V = 3806.9 (9) Å³
Z = 8
Mo K radiation
= 0.21 mm^-1
T = 273 K
0.19 × 0.16 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.962, T_max = 0.988
9821 measured reflections
3379 independent reflections
2910 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.171
S = 1.05
3379 reflections
246 parameters
H-atom parameters constrained
_max = 0.73 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O6	0.86	2.10	2.723 (3)	129
N1-H1O2ⁱ	0.86	2.58	3.160 (3)	125
O6-H6O2ⁱⁱ	0.82	1.91	2.709 (3)	166
O4-H16O3ⁱ	0.85	2.00	2.828 (5)	166
O5-H18N1ⁱⁱⁱ	0.85	2.51	3.35 (3)	174
C2-H2O3	0.93	2.56	2.915 (4)	103
C5-H5O1^iv	0.93	2.55	3.392 (3)	150
C7-H7BO2ⁱ	0.96	2.44	3.325 (3)	154
C8-H8O1^iv	0.93	2.43	3.353 (3)	172
C15-H15BO3ⁱⁱ	0.97	2.50	3.444 (4)	166
C16-H16CO5^v	0.96	2.51	3.42 (3)	160
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y, z+1; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (v) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2871 ).

Acknowledgements

The authors thank the Program for New Century Excellent Talents in Universities for a research grant.

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bu, X. H., Gao, Y. X., Chen, W. & Zhang, R. H. (2001). J. Rare Earth, 19, 70-75.
Ranford, J. D., Vittal, J. J. & Wang, Y. M. (1998). Inorg. Chem. 37, 1226-1231.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds