Di-n-butyl­ammonium 2-(3,5-di-tert-butyl-4-hydroxy­benzyl­sulfan­yl)nicotinate

Mansor, S.; Yehye, W.A.; Ariffin, A.; Rahman, N.A.; Ng, S.W.

doi:10.1107/S1600536808026202

Volume 64
Part 9
Page o1799
September 2008

Received 11 August 2008
Accepted 13 August 2008
Online 20 August 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.110
Data-to-parameter ratio = 20.2
Details

Di-n-butylammonium 2-(3,5-di-tert-butyl-4-hydroxybenzylsulfanyl)nicotinate

Shahirah Mansor,^a Wagee A. Yehye,^a Azhar Ariffin,^a Noorsaadah Abdul Rahman ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The asymmetric unit of the title compound, C₈H₂₀N⁺·C₂₁H₂₆NO₃S^-, contains two indpendent ion pairs which are disposed about a psuedo-inversion center, generating an ammonium-carboxylate N-HO hydrogen-bonded four-component cluster. In the crystal structure, adjacent clusters are linked by hydroxy-carboxylate O-HO hydrogen bonds, forming a chain.

Related literature

For the applications of hindered phenol-based antioxidants, see: Kim & Lee (2003); Um et al. (2005).

Experimental

Crystal data

C₈H₂₀N⁺·C₂₁H₂₆NO₃S^-
M_r = 502.74
Orthorhombic, P c a 2₁
a = 23.4451 (3) Å
b = 18.7712 (3) Å
c = 12.9657 (2) Å
V = 5706.11 (15) Å³
Z = 8
Mo K radiation
= 0.14 mm^-1
T = 293 (2) K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.965, T_max = 0.993
53030 measured reflections
13074 independent reflections
10355 reflections with I > 2(I)
R_int = 0.066

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.110
S = 1.07
13074 reflections
647 parameters
1 restraint
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.32 e Å^-3
Absolute structure: Flack (1983), 6221 Friedel pairs
Flack parameter: 0.03 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H32O2	0.88	1.95	2.826 (2)	172
N3-H31O5	0.88	1.99	2.820 (3)	157
N4-H42O2	0.88	1.97	2.816 (3)	160
N4-H41O5	0.88	1.96	2.834 (2)	172
O3-H3oO1ⁱ	0.84	2.04	2.708 (3)	135
O6-H6oO4ⁱⁱ	0.84	1.81	2.651 (3)	175
Symmetry codes: (i) x, y, z-1; (ii) x, y, z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2682 ).

Acknowledgements

We thank the University of Malaya (grant No. FS338/2008 A) for supporing this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Kim, T. H. & Lee, N. (2003). Bull. Kor. Chem. Soc., 24, 1809-1813.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Um, S.-I., Kang, Y.-H. & Lee, J.-Y. (2005). Dyes Pigm. 64, 93-99.
Westrip, S. P. (2008). publCIF. In preparation.

organic compounds