4,4′-Methyl­enedianilinium bis­(3-carb­oxy-4-hydroxy­benzene­sulfonate) monohydrate

Du, G.; Liu*, Z.; Chu, Q.; Li, Z.; Zhang, S.

doi:10.1107/S1600536808029115

Volume 64
Part 10
Pages o1947-o1948
October 2008

Received 1 September 2008
Accepted 10 September 2008
Online 17 September 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.040
wR = 0.106
Data-to-parameter ratio = 14.7
Details

4,4'-Methylenedianilinium bis(3-carboxy-4-hydroxybenzenesulfonate) monohydrate

Guihuan Du,^a ^* Zuli Liu,^a Qian Chu,^b Zhen Li ^b and Suming Zhang ^b

^aDepartment of Physics, Huazhong University of Science and Technology, Wuhan 430074, People's Republic of China, and ^bTongji Hospital, Huazhong University of Science and Technology, Wuhan 430070, People's Republic of China
Correspondence e-mail: duguihuan@126.com

Co-crystallization of 4,4'-methylenediphenylamine (MDA) and 5-sulfosalicylic acid (5-H₂SSA) yields the title salt, C₁₃H₁₆N₂²⁺·2C₇H₅O₆S^-·H₂O. The asymmetric unit is comprised of one dication, two anions and one water molecule. In the crystal structure, the components of the salt are linked by a combination of intermolecular O-HO, N-HO and weak C-HO hydrogen bonds into a three-dimensional framework. In addition, two weak - interactions [with centroid-centroid distances of 3.8734 (15) and 3.7465 (15) Å] and one C-H interaction further stabilize the crystal structure.

Related literature

For related structures, see: Smith (2005); Smith et al. (2005a,b, 2006). For background information, see: Wang et al. (2008).

Experimental

Crystal data

C₁₃H₁₆N₂²⁺·2C₇H₅O₆S^-·H₂O
M_r = 652.63
Monoclinic, P 2₁
a = 5.8769 (1) Å
b = 18.8659 (3) Å
c = 12.9864 (2) Å
= 94.668 (1)°
V = 1435.06 (4) Å³
Z = 2
Mo K radiation
= 0.26 mm^-1
T = 296 (2) K
0.40 × 0.30 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.894, T_max = 0.990
16262 measured reflections
6379 independent reflections
5671 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.106
S = 1.09
6379 reflections
433 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.33 e Å^-3
_min = -0.17 e Å^-3
Absolute structure: Flack (1983), 3009 Friedel pairs
Flack parameter: 0.05 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO4ⁱ	0.90 (4)	2.03 (4)	2.896 (4)	161 (3)
N1-H1BO1ⁱⁱ	0.82 (4)	2.47 (3)	2.751 (3)	101 (3)
N1-H1BO12	0.82 (4)	2.01 (4)	2.814 (4)	168 (3)
N1-H1CO11ⁱⁱⁱ	0.99 (4)	1.92 (4)	2.870 (3)	161 (3)
N2-H2AO4ⁱⁱⁱ	0.82 (4)	2.07 (4)	2.801 (4)	149 (3)
N2-H2CO5	0.97 (4)	2.16 (4)	2.927 (4)	135 (3)
N2-H2BO6	0.84 (4)	2.20 (4)	2.889 (4)	139 (3)
N2-H2CO3ⁱ	0.97 (4)	2.19 (4)	2.940 (3)	134 (3)
O2-H2DO11^iv	0.80 (4)	1.91 (4)	2.688 (3)	164 (4)
O3-H3AO1	0.86 (4)	1.77 (4)	2.569 (3)	153 (4)
O8-H8AO13^v	0.87 (5)	1.76 (5)	2.598 (4)	160 (4)
O9-H9AO7	0.86 (5)	1.96 (4)	2.678 (3)	141 (4)
O9-H9AO6^vi	0.86 (5)	2.38 (4)	2.872 (3)	117 (3)
O13-H13AO10^vii	0.83 (8)	1.93 (8)	2.759 (4)	176 (7)
O13-H13BO6	0.89 (7)	2.39 (7)	3.064 (4)	132 (6)
C2-H2O5^viii	0.93	2.54	3.452 (4)	168
C6-H6O12	0.93	2.48	3.210 (3)	136
C12-H12O9^ix	0.93	2.55	3.428 (4)	158
C16-H16Cg^x	0.93	2.85	3.727 (3)	157
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (ii) x, y-1, z; (iii) x+1, y, z; (iv) x+1, y+1, z; (v) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (vi) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (vii) x, y+1, z; (viii) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (ix) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (x) $[-x+1, y+{\script{1\over 2}}, -z+2]$ . Cg is the centroid of the C8-C13 ring.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2691 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China under grant Nos. 10574047, 10574048 and 20490210. This work was also supported by the National 973 Project under grant No. 2006CB921605.

References

Bruker (2007). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G. (2005). Acta Cryst. E61, o3398-o3400.
Smith, G., Wermuth, U. D. & White, J. M. (2005a). Acta Cryst. E61, o313-o316.
Smith, G., Wermuth, U. D. & White, J. M. (2005b). Acta Cryst. C61, o105-o109.
Smith, G., Wermuth, U. D. & Healy, P. C. (2006). Acta Cryst. E62, o2313-o2315.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Wang, Z., Yao, K., Liu, Z. & Xu, H. (2008). Acta Cryst. E64, o1192.

organic compounds