N-Butyl-4-butyl­imino-2-methyl­pentan-2-aminium (E)-quercetinate

Grosu, I.-G.; Borodi, G.; Pop, M.M.

doi:10.1107/S1600536812031170

Volume 68
Part 8
Page o2450
August 2012

Received 6 June 2012
Accepted 9 July 2012
Online 14 July 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.065
wR = 0.233
Data-to-parameter ratio = 18.7
Details

N-Butyl-4-butylimino-2-methylpentan-2-aminium (E)-quercetinate

Ioana-Georgeta Grosu,^a Gheorghe Borodi ^a and Mihaela Maria Pop ^a ^*

^aNational Institute for R&D of Isotopic and Molecular Technologies, PO Box 700, Cluj-Napoca R-400293, Romania
Correspondence e-mail: mihaela.pop@itim-cj.ro

The title salt, C₁₄H₃₁N₂⁺·C₁₅H₉O₇^-, was obtained in the reaction of quercetin with n-butylamine in a mixture of acetone and hexane. The crystal structure determination shows that the quercetin donates one of its phenol H atoms to the N-butyl-4-butylimino-2-methylpentan-2-amine molecule. The crystal structure of the salt is stabilized by intramolecular (N-HN for the cation and O-HO for the anion) and intermolecular hydrogen bonding (N-HO between cation-anion pairs and O-HO between anions). Quercetin molecules form dimers connected into a two-dimensional network. The dihedral angle between the quercetin ring systems is 19.61 (8)°.

Related literature

For the antioxidant activity of quercetin, see: Young et al. (1999). For related co-crystal structures, see: Clarke et al. (2010); Kavuru et al. (2010).

Experimental

Crystal data

C₁₄H₃₁N₂⁺·C₁₅H₉O₇^-
M_r = 528.63
Monoclinic, P 2₁ /n
a = 11.4017 (7) Å
b = 13.1730 (5) Å
c = 19.1961 (9) Å
= 104.438 (6)°
V = 2792.1 (2) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.3 × 0.2 × 0.1 mm

Data collection

SuperNova, Dual, Cu at zero, Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ). T_min = 0.647, T_max = 1.000
25155 measured reflections
6574 independent reflections
4881 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.233
S = 1.57
6574 reflections
352 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2B-H2BAO6A	0.9	1.87	2.765 (2)	171
N2B-H2BBN1B	0.9	2.05	2.749 (3)	134
O7A-H7AO5A	0.82	1.92	2.642 (2)	147
O1A-H1AO6Aⁱ	0.82	1.73	2.544 (2)	172
O2A-H2AO6Aⁱ	0.82	1.85	2.6637 (19)	173
O4A-H4AO2Aⁱⁱ	0.82	2.01	2.771 (2)	154
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2204 ).

Acknowledgements

This work was supported by ANCS, project No. POSCCE ID536.

References

Clarke, H. D., Arora, K. K., Bass, H., Kavuru, P., Ong, T. T., Pujari, T., Wojtas, L. & Zaworotko, M. J. (2010). Cryst. Growth Des. 10, 2152-2167.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Kavuru, P., Aboarayes, D., Arora, K. K., Clarke, H. D., Kennedy, A., Marshall, L., Ong, T. T., Perman, J., Pujari, T., Wojtas, L. & Zaworotko, M. J. (2010). Cryst. Growth Des. 10, 3568-3584.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Young, J. F., Nielsen, S. E., Haraldsdottir, J., Daneshvar, B., Lauridsen, S. L., Knuthsen, P., Crozier, A., Sandström, B. & Dragsted, L. O. (1999). Am. J. Clin. Nutr. 69, 87-94.

organic compounds