5-Carb­oxy-2,4-dihy­droxy­anilinium chloride dihydrate

Naz, S.S.; Islam, N.U.; Tahir, M.N.

doi:10.1107/S1600536811000559

Volume 67
Part 2
Page o299
February 2011

Received 4 January 2011
Accepted 5 January 2011
Online 8 January 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.115
Data-to-parameter ratio = 18.3
Details

5-Carboxy-2,4-dihydroxyanilinium chloride dihydrate

Syeda Sohaila Naz,^a Nazar Ul Islam ^a and M. Nawaz Tahir ^b ^*

^aInstitute of Chemical Sciences, University of Peshawar, Peshawar, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C₇H₈NO₄⁺·Cl^-·2H₂O, the organic molecule is almost planar with an r.m.s. deviation of 0.0164 Å for all non-H atoms. An S(6) ring motif is formed due to an intramolecular O-HO hydrogen bond. In the crystal, the molecules are linked into a three-dimensional network by N-HCl, N-HO, O-HCl and O-HO hydrogen bonds.

Related literature

For a related structure, see: Naz et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₇H₈NO₄⁺·Cl^-·2H₂O
M_r = 241.63
Triclinic, $[P \overline 1]$
a = 6.0285 (8) Å
b = 7.9597 (8) Å
c = 10.9570 (13) Å
= 100.135 (5)°
= 97.162 (4)°
= 92.921 (5)°
V = 512.10 (11) Å³
Z = 2
Mo K radiation
= 0.38 mm^-1
T = 296 K
0.28 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.935, T_max = 0.965
8850 measured reflections
2548 independent reflections
1853 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.115
S = 1.03
2548 reflections
139 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O6	0.82	1.88	2.6945 (19)	171
O3-H3O2	0.82	1.96	2.672 (2)	145
O4-H4ACl1ⁱ	0.82	2.21	3.0097 (15)	164
N1-H1AO6ⁱⁱ	0.89	2.02	2.903 (2)	169
N1-H1BO5ⁱⁱⁱ	0.89	1.96	2.853 (2)	178
N1-H1CCl1^iv	0.89	2.35	3.1950 (18)	157
O5-H5AO2^v	0.86	2.16	2.935 (2)	149
O5-H5BCl1	0.85	2.41	3.1494 (15)	146
O6-H6ACl1	0.88	2.27	3.1386 (16)	174
O6-H6BO5^vi	0.86	1.99	2.850 (2)	173
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) x-1, y, z+1; (iv) -x+1, -y+1, -z+1; (v) x+1, y, z; (vi) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2650 ).

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha. Pakistan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Naz, S. S., Islam, N. U. & Tahir, M. N. (2010). Acta Cryst. E66, o2372.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds