Cyclo­hexane-1,4-dicarb­oxy­lic acid–pyridinium-4-olate (1/1)

Adriana Cruz-Enríquez; Hector J Peinado-Guevara; Viviana Reyes-Marquez; Herbert Höpfl; José J Campos-Gaxiola

doi:10.1107/S160053681300754X

. 2013 Mar 28;69(Pt 4):o591. doi: 10.1107/S160053681300754X

Cyclohexane-1,4-dicarboxylic acid–pyridinium-4-olate (1/1)

Adriana Cruz-Enríquez ^a,^*, Hector J Peinado-Guevara ^a, Viviana Reyes-Marquez ^b, Herbert Höpfl ^b, José J Campos-Gaxiola ^a

PMCID: PMC3629634 PMID: 23634121

Abstract

In the title adduct, C₅H₅NO·C₈H₁₂O₄, the heterocycle exists in its zwitterionic form. The cyclohexane ring exhibits a chair conformation with the carboxylic acid groups in equatorial and axial orientations. In the crystal, molecules are linked through charge-assisted O—H⋯O⁻, N⁺—H⋯O⁻ and N⁺—H⋯O hydrogen bonds, and an additional series of C—H⋯O contacts, giving a pleated two-dimensional hydrogen-bonded network parallel to (-204).

Related literature

For reports on supramolecular crystal engineering and potential applications of co-crystals, see: Desiraju (1995 ▶); Simon & Bassoul (2000 ▶); Weyna et al. (2009 ▶); Aakeröy et al. (2010 ▶); Yan et al. (2012 ▶). For related structures, see: Bhogala et al. (2005 ▶); Shattock et al. (2008 ▶); Yu (2012 ▶).

Experimental

Crystal data

C₅H₅NO·C₈H₁₂O₄
M _r = 267.28
Monoclinic,
a = 11.749 (2) Å
b = 11.618 (2) Å
c = 10.8010 (19) Å
β = 115.383 (2)°
V = 1332.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.50 × 0.43 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.95, T _max = 0.98
12552 measured reflections
2345 independent reflections
2229 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.072
wR(F ²) = 0.161
S = 1.02
2345 reflections
181 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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

Supplementary Material

Click here for additional data file.^{(18.1KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681300754X/pk2472sup1.cif

e-69-0o591-sup1.cif^{(18.1KB, cif)}

Click here for additional data file.^{(115.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300754X/pk2472Isup2.hkl

e-69-0o591-Isup2.hkl^{(115.3KB, hkl)}

Click here for additional data file.^{(5.3KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681300754X/pk2472Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1′⋯O5	0.84	1.82	2.638 (3)	165
O3—H3′⋯O5ⁱ	0.84	1.76	2.594 (2)	175
N1—H1⋯O4ⁱⁱ	0.84	2.29	2.921 (3)	132
N1—H1⋯O5ⁱⁱⁱ	0.84	2.39	3.038 (3)	134
C1—H1A⋯O2^iv	0.98	2.67	3.625 (4)	162
C11—H11⋯O2ⁱⁱⁱ	0.93	2.62	3.420 (5)	143
C12—H12⋯O4ⁱⁱ	0.93	2.47	3.014 (4)	117

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

This work was supported financially by the Universidad Autónoma de Sinaloa (PROFAPI 2012/049).

supplementary crystallographic information

Comment

The engineering of novel materials via non-covalent synthesis has developed as a very attractive and potential area of research because of its importance in biological systems, molecular recognition (Simon et al., 2000; Aakeröy et al., 2010), pharmaceutical chemistry (Weyna et al., 2009) and materials chemistry (Yan et al., 2012). Aromatic carboxylic acids form reliable supramolecular synthons for the construction of novel organic networks by hydrogen bonding and π-π interactions (Desiraju, 1995), and numerous studies have focused on hydrogen bonding between carboxylic acids and pyridine derivatives (Bhogala et al., 2005; Shattock et al. 2008; Yu, 2012). Herein, we report on the solid-state structure of a 1:1 co-crystal formed between cyclohexane-1,4-dicarboxylic acid and pyridin-4-ol. The molecular components of the title compound are shown in Fig. 1. The asymmetric unit contains one cyclohexane-1,4-dicarboxylic acid and one pyridin-4-ol molecule in the zwitterionic form. The cyclohexane ring exhibits a chair conformation with the carboxylic groups in equatorial and axial orientation, as denoted by the C7—C1—C2—C3 [-177.7 (2)°] and C8—C4—C5—C6 [75.7 (3)°] torsion angles, respectively. In the crystal, the molecular entities are linked through charge-assisted O—H···O^-, N⁺—H···O^- and N⁺—H···O hydrogen bonds and an additional series of C—H···O contacts to give a pleated two-dimensional hydrogen-bonded network parallel to (-204) (Fig. 2, Table 1).

Experimental

C₅H₅NO.C₈H₁₂O₄ was prepared from a solution of C₅H₅NO (0.05 g, 0.53 mmol) and C₈H₁₂O₄ (0.09 g, 0.53 mmol) in CH₃OH (5 ml), which was stirred for a few minutes at room temperature, giving a clear transparent solution. After evaporation of the solvent, colorless crystals suitable for single-crystal X-ray diffraction had formed in about 51% yield. IR (KBr): 3471, 3276, 3131, 3092, 2937, 2863, 1709, 1632, 1576, 1509, 1416, 1364, 1331, 1316, 1229, 1170, 1001 cm^-1.