2-Amino-5-chloro­pyridinium 2-carb­oxy­benzoate–benzene-1,2-dicarb­oxy­lic acid (3/1)

Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536810035853

Volume 66
Part 10
Page o2535
October 2010

Received 1 September 2010
Accepted 7 September 2010
Online 11 September 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.101
Data-to-parameter ratio = 18.6
Details

2-Amino-5-chloropyridinium 2-carboxybenzoate-benzene-1,2-dicarboxylic acid (3/1)

Madhukar Hemamalini ^a and Hoong-Kun Fun ^a ^*⁺

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title compound, 3C₅H₆ClN₂⁺·3C₈H₅O₄^-·C₈H₆O₄, contains three independent 2-amino-5-chloropyridinium cations, three independent hydrogen phthalate anions and one phthalic acid molecule. In the crystal structure, there are two kinds of supramolecular tapes. One is formed by two independent cations with two anions through N-HO and C-HO hydrogen bonds. Another one is formed by the other cation and anion, and the phthalic acid molecule via N-HO, O-HO and C-HO hydrogen bonds. These two tapes are connected by an O-HO hydrogen bond, forming a double-tape structure.

Related literature

For details of hydrogen bonding, see: Jeffery (1997). For details of structures incorporating phthalic acid, see: Dale et al. (2004); Ballabh et al. (2005). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

3C₅H₆ClN₂⁺·3C₈H₅O₄^-·C₈H₆O₄
M_r = 1050.19
Triclinic, $[P \overline 1]$
a = 9.8522 (2) Å
b = 14.0242 (2) Å
c = 17.4312 (3) Å
= 68.920 (1)°
= 87.507 (1)°
= 83.906 (1)°
V = 2234.54 (7) Å³
Z = 2
Mo K radiation
= 0.29 mm^-1
T = 100 K
0.49 × 0.22 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.870, T_max = 0.940
63061 measured reflections
12966 independent reflections
11359 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.101
S = 1.03
12966 reflections
696 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.44 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2C-H2CO3C	0.82	1.58	2.4004 (13)	177
O2A-H1OAO3A	0.86	1.55	2.4123 (13)	177
O2B-H1OBO3B	0.89	1.52	2.4126 (14)	178
O2X-H1OXO4C	0.88 (2)	1.76 (2)	2.6091 (12)	163 (2)
O4X-H2OXO1Aⁱ	0.83 (2)	1.86 (2)	2.6880 (13)	177 (2)
N2A-H2NAO1Bⁱⁱ	0.895 (18)	2.018 (18)	2.9095 (14)	173.4 (19)
N1B-H1NBO4Aⁱⁱⁱ	0.92 (2)	1.69 (2)	2.5938 (14)	169 (2)
N2B-H2NBO3Aⁱⁱⁱ	0.87 (2)	2.12 (2)	2.9570 (14)	161.8 (17)
N1C-H1NCO4B	0.94 (2)	1.69 (2)	2.6169 (16)	168 (2)
N2C-H3NCO3B	0.83 (2)	2.11 (2)	2.9279 (15)	168.4 (19)
C4A-H4AAO2Bⁱⁱ	0.93	2.26	3.1614 (14)	164
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2597 ).

Acknowledgements

MH and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Ballabh, A., Trivedi, D. R. & Dastidar, P. (2005). Cryst. Growth Des. 5, 1548-1553.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Dale, S. H., Elsegood, M. R. J., Hemmings, M. & Wilkinson, A. L. (2004). CrystEngComm, 6, 207-214.
Jeffery, J. A. (1997). An Introduction to Hydrogen Bonding. Oxford University Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds