4-[(E)-2-(Pyridin-2-yl)ethen­yl]pyridine–terephthalic acid (2/1)

Castro-Montes, P.; Guerrero-Alvarez, J.A.; Hopfl, H.; Campos-Gaxiola, J.J.; Cruz-Enriquez, A.

doi:10.1107/S1600536812046284

Volume 68
Part 12
Pages o3383-o3384
December 2012

Received 5 November 2012
Accepted 8 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.055
wR = 0.149
Data-to-parameter ratio = 12.7
Details

4-[(E)-2-(Pyridin-2-yl)ethenyl]pyridine-terephthalic acid (2/1)

Paola Castro-Montes,^a Jorge A. Guerrero-Alvarez,^b Herbert Hopfl,^b Jose J. Campos-Gaxiola ^a and Adriana Cruz-Enriquez ^a ^*

^aFacultad de Ingenieria Mochis, Universidad Autonoma de Sinaloa, Fuente Poseidon y Prol. A. Flores S/N, CP 81223, C.U. Los Mochis, Sinaloa, Mexico, and ^bCentro de Investigaciones Quimicas, Universidad Autonoma del Estado de Morelos, Av. Universidad 1001, CP 62210, Cuernavaca, Morelos, Mexico
Correspondence e-mail: cenriqueza@yahoo.com.mx

The title 2:1 co-crystal, 2C₁₂H₁₀N₂·C₈H₆O₄, crystallizes with one molecule of 4-[(E)-2-(pyridin-2-yl)ethenyl]pyridine (A) and one half-molecule of terephthalic acid (B) in the asymmetric unit. In the crystal, the components are linked through heterodimeric COOHN_pyridine synthons, forming linear aggregates of composition -A-B-A-B-. Further linkage through weak C-HO and C-H [pi] interactions gives two-dimensional hydrogen-bonded undulating sheets propagating in the [100] and [010] directions. These layers are connected through additional weak C-HO contacts, forming a three-dimensional structure.

Related literature

For reports on supramolecular crystal engineering and potential applications of co-crystals, see: Desiraju (1995); Simon & Bassoul (2000); Bhogala & Nangia (2003); Weyna et al. (2009); Yan et al. (2012). For background to related co-crystals, see: Santra et al. (2008); Moon & Park (2012); Ebenezer & Muthiah (2012).

Experimental

Crystal data

C₁₂H₁₀N₂·0.5C₈H₆O₄
M_r = 265.28
Monoclinic, P 2₁ /n
a = 6.3821 (8) Å
b = 32.301 (4) Å
c = 6.8721 (8) Å
= 111.440 (2)°
V = 1318.6 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.48 × 0.41 × 0.34 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.96, T_max = 0.97
12715 measured reflections
2328 independent reflections
2119 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.149
S = 1.17
2328 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.14 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N2/C12-C16 pyridine ring.

D-HA	D-H	HA	DA	D-HA
O1-H1'N1ⁱ	0.84	1.77	2.604 (2)	177
C9-H9O2ⁱⁱ	0.93	2.67	3.285 (3)	125
C13-H13O2ⁱⁱⁱ	0.93	2.52	3.396 (2)	157
C5-H5O2^iv	0.93	2.64	3.135 (2)	114
C16-H16Cg^v	0.93	2.86	3.627 (3)	141
Symmetry codes: (i) x, y, z+1; (ii) x, y, z-1; (iii) x-1, y, z; (iv) x-1, y, z-1; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al. 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2525 ).

Acknowledgements

This work was supported financially by the Universidad Autónoma de Sinaloa (PROFAPI 2011/048). PCM thanks the Consejo Nacional de Ciencia y Tecnologia (CONACYT) for support in the form of a scholarship.

References

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Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. (1995). Angew. Chem. Int. Ed. 34, 2311-2327.
Ebenezer, S. & Muthiah, P. T. (2012). Cryst. Growth Des. 12, 3766-3785.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Simon, J. & Bassoul, P. (2000). In Design of Molecular Materials: Supramolecular Engineering. Berlin: Wiley-VCH.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Weyna, D. R., Shattock, T., Vishweshwar, P. & Zaworotko, M. J. (2009). Cryst. Growth Des. 9, 1106-1123.
Yan, D., Delori, A., Lloyd, G. O., Patel, B., Friscic, T., Day, G. M., Bucar, D. J., Jones, W., Min Wei, J. L., Evans, D. G. & Duan, X. (2012). CrystEngComm, 14, 5121-5123.

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