Di-tert-butyl 2,2′-(biphenyl-2,2′-diyl­dioxy)diacetate

Ali, Q.; Ibad, F.; Shah, M.R.; VanDerveer, D.

doi:10.1107/S1600536808019764

Volume 64
Part 8
Page o1408
August 2008

Received 23 April 2008
Accepted 28 June 2008
Online 5 July 2008

Key indicators
Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.113
Data-to-parameter ratio = 15.5
Details

Di-tert-butyl 2,2'-(biphenyl-2,2'-diyldioxy)diacetate

Qamar Ali,^a Farooq Ibad,^a Muhammad Raza Shah ^a ^* and Donald VanDerveer ^b

^aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bChemistry Department, Clemson University, Clemson, SC 29634-0973, USA
Correspondence e-mail: raza_shahm@yahoo.com

The title compound, C₂₄H₃₀O₆, does not exhibit [pi] - [pi] interactions due to the steric effect of the bulky tert-butyl groups present in the molecule. The presence of these groups at the 2 and 2' positions hinders the free motion of the benzene rings relative to each other, causing them to adopt an antiperiplanar arrangement. The benzene rings are twisted by just under 50.96 (17)° with respect to each other. The carbonyl groups within the molecule are directed in different directions, one towards the biphenyl group and the other away from it. The molecules are linked together by C=OH-C hydrogen bonds.

Related literature

For general background on chemical and biological studies of biphenyl compounds, see: Toshiaki et al. (2007); Kamoda et al. (2006); Makarov et al. (2005); Weisburger et al. (1967); Spivey et al. (1999); Sisson et al. (2006); Litvinchuk et al. (2004); Baudry et al. (2006). For the crystal structures of related compounds, see: Ali et al. (2008); Ibad et al. (2008).

Experimental

Crystal data

C₂₄H₃₀O₆
M_r = 414.48
Triclinic, $[P \overline 1]$
a = 7.7458 (15) Å
b = 12.112 (2) Å
c = 13.480 (3) Å
= 67.36 (3)°
= 82.11 (3)°
= 82.68 (3)°
V = 1152.3 (4) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 153 (2) K
0.48 × 0.38 × 0.19 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998) T_min = 0.960, T_max = 0.984
8742 measured reflections
4191 independent reflections
3687 reflections with I > 2(I)
R_int = 0.012

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.113
S = 1.06
4191 reflections
271 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2AO2ⁱ	0.99	2.51	3.482 (2)	166
C20-H20CO5ⁱⁱ	0.98	2.47	3.414 (2)	162
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2127 ).

Acknowledgements

The authors thank the Organization for the Prohibition of Chemical Weapons for financial support.

References

Ali, Q., Shah, M. R. & VanDerveer, D. (2008). Acta Cryst. E64, o910.
Baudry, Y., Litvinchuk, S., Mareda, J., Nishihara, M., Pasnin, D., Shah, M. R., Sakai, N. & Matile, S. (2006). Adv. Funct. Mater. 16, 169-179.
Ibad, F., Mustafa, A., Shah, M. R. & VanDerveer, D. (2008). Acta Cryst. E64, o1130-o1131.
Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.
Kamoda, O., Anzai, K., Mizoguchi, J., Shiojiri, M., Yanagi, T., Nishino, T. & Kamiya, S. (2006). Antimicrob. Agents Chemother. 50, 3062-3069.
Litvinchuk, S., Bollot, G., Mareda, J., Som, A., Ronan, D., Shah, M. R., Perrottet, P., Sakai, N. & Matile, S. (2004). J. Am. Chem. Soc. 126, 10067-10075.
Makarov, V. A., Riabova, O. B., Granik, V. G., Wutzler, P. & Schmidtke, M. (2005). J. Antimicrob. Chemother. 55, 483-488.
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sisson, A. L., Shah, M. R., Bhosale, S. & Matile, S. (2006). Chem. Soc. Rev. 35, 1269-1286.
Spivey, A. C., Fekner, T., Spey, S. E. & Adams, H. (1999). J. Org. Chem. 64, 9430-9443.
Toshiaki, M., Yoshihisa, K., Kouhei, K., Shizue, K., Yoshika, F., Toshiaki, S. & Yutaka, G. (2007). J. Pharm. Sci. 103, 238-239.
Weisburger, J. H., Mantel, N., Weisburger, E. K., Hadidian, Z. & Fredrickson, T. (1967). Nature (London), 213, 930-931.

organic compounds