Isopropyl­aminium 2-carb­oxy-4,5-di­chloro­benzoate

Smith, G.; Wermuth, U.D.

doi:10.1107/S1600536809052672

Volume 66
Part 1
Page o133
January 2010

Received 25 November 2009
Accepted 8 December 2009
Online 12 December 2009

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.070
Data-to-parameter ratio = 13.9
Details

Isopropylaminium 2-carboxy-4,5-dichlorobenzoate

Graham Smith ^a ^* and Urs D. Wermuth ^b

^aSchool of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia, and ^bSchool of Biomolecular and Physical Sciences, Griffith University, Nathan, Queensland 4111, Australia
Correspondence e-mail: g.smith@qut.edu.au

In the structure of the 1:1 proton-transfer compound of isopropylamine with 4,5-dichlorophthalic acid, C₃H₁₀N⁺·C₈H₃Cl₂O₄^-, the three cation H-atom donors associate with three separate carboxyl O-atom anion acceptors, giving conjoint cyclic R₄⁴(12), R₄⁴(16) hydrogen-bonding cation-anion interactions in a one-dimensional ribbon structure. In the anions, the carboxyl groups lie slightly out of the plane of the benzene ring [maximum deviations = 0.439 (1) for a carboxylic acid O atom and 0.433 (1) Å for a carboxylate O atom]. However, the syn-related proton of the carboxylic acid group forms the common short intramolecular O-HO_carboxyl hydrogen bond.

Related literature

For the structures of other hydrogen 4,5-dichlorophthalate salts, see: Mattes & Dorau (1986); Mallinson et al. (2003); Bozkurt et al. (2006); Odabasoglu & Büyükgüngör (2007); Smith et al. (2007, 2008a,b, 2009a,b,c); Smith & Wermuth (2010). For graph-set analysis see: Etter et al. (1990).

Experimental

Crystal data

C₃H₁₀N⁺·C₈H₃Cl₂O₄^-
M_r = 294.12
Monoclinic, P 2₁ /n
a = 5.8362 (7) Å
b = 21.040 (2) Å
c = 10.3641 (13) Å
= 95.064 (12)°
V = 1267.7 (3) Å³
Z = 4
Mo K radiation
= 0.52 mm^-1
T = 200 K
0.40 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Gemini-S CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.942, T_max = 0.982
8508 measured reflections
2484 independent reflections
2103 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.070
S = 1.11
2484 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.24 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O12-H12O21	1.00 (3)	1.45 (3)	2.4507 (16)	179 (3)
N1A-H11AO11	0.977 (18)	1.875 (18)	2.8175 (17)	161.2 (15)
N1A-H12AO21ⁱ	0.876 (19)	2.021 (18)	2.8593 (16)	159.6 (16)
N1A-H13AO22ⁱⁱ	0.92 (2)	1.98 (2)	2.8869 (17)	168.8 (15)
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x, y, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2696 ).

Acknowledgements

The authors acknowledge financial support from the Australian Research Council, the School of Physical and Chemical Sciences, Queensland University of Technology, and the School of Biomolecular and Physical Sciences, Griffith University.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Bozkurt, E., Kartal, I., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o4258-o4260.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Mallinson, P. R., Smith, G. T., Wilson, C. C., Grech, E. & Wozniak, K. (2003). J. Am. Chem. Soc. 125, 4259-4270.
Mattes, R. & Dorau, A. (1986). Z. Naturforsch. Teil B, 41, 808-814.
Odabasoglu, M. & Büyükgüngör, O. (2007). Acta Cryst. E63, o4374-o4375.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G. & Wermuth, U. D. (2010). J. Chem. Crystallogr. In the press.
Smith, G., Wermuth, U. D. & White, J. M. (2007). Acta Cryst. E63, o4276-o4277.
Smith, G., Wermuth, U. D. & White, J. M. (2008a). Acta Cryst. C64, o180-o183.
Smith, G., Wermuth, U. D. & White, J. M. (2008b). Acta Cryst. C64, o532-o536.
Smith, G., Wermuth, U. D. & White, J. M. (2009a). Acta Cryst. C65, o103-o107.
Smith, G., Wermuth, U. D. & White, J. M. (2009b). Acta Cryst. E65, o2111.
Smith, G., Wermuth, U. D. & White, J. M. (2009c). Acta Cryst. E65, o2333.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds