(1S*,2R*,3S*,4R*,5R*)-5-Tetra­decyloxy­methyl-7-oxabicyclo­[2.2.1]heptane-2,3-dicarb­oxy­lic anhydride

Kelly, C.N.; Sulon, S.M.; Pham, L.N.; Xiang, K.R.; Sykora, R.E.; Forbes, D.C.

doi:10.1107/S1600536812046259

Volume 68
Part 12
Page o3374
December 2012

Received 6 November 2012
Accepted 8 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.108
Data-to-parameter ratio = 15.9
Details

(1S,2R,3S,4R,5R*)-5-Tetradecyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

Colin N. Kelly,^a Sarah M. Sulon,^b Lam N. Pham,^c Kang Rui Xiang,^c Richard E. Sykora ^c and David C. Forbes ^c ^*

^aDepartment of Chemistry and Biochemistry, Oberlin College, Oberlin, OH 44074, USA,^bBiology Department, Elizabethtown College, Elizabethtown, PA 17022, USA, and ^cDepartment of Chemistry, University of South Alabama, Mobile, AL 36688, USA
Correspondence e-mail: dforbes@southalabama.edu

In the title compound, C₂₃H₃₈O₅, the oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride unit has a normal geometry and the tetradecoxymethyl side chain is fully extended. In the crystal, molecules are linked head-to-head by C-HO hydrogen bonds, forming two-dimensional networks propagating along the a and c-axis directions.

Related literature

Olefinic hydrogenation of an oxabicyclo[2.2.1]hept-5-ene derivative using catalytic quantities of 10% Pd on carbon as catalyst afforded the title compound. For reviews on the Diels-Alder reaction, see: Oppolzer (1991); Pindur et al. (1993). For a review on asymmetric cycloaddion processes, see: Pellissier (2012). For a review on catalytic hydrogenations, see: Brieger & Nestrick (1974). For a review on asymmetric catalytic hydrogenation processes, see: Knowles (2002). For discussions on reaction mechanisms with specifics on kinetic and thermodynamic control, see: Lowry & Richardson (1987); Smith (2012). For a discussion on Diels-Alder selectivity using maleic anhydride, see: Palmer (2004).

Experimental

Crystal data

C₂₃H₃₈O₅
M_r = 394.53
Monoclinic, P 2₁ /n
a = 6.8541 (5) Å
b = 35.206 (4) Å
c = 9.2992 (7) Å
= 99.060 (7)°
V = 2216.0 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 180 K
0.47 × 0.17 × 0.02 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.865, T_max = 1.000
9120 measured reflections
4053 independent reflections
2974 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.108
S = 1.04
4053 reflections
255 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1O1ⁱ	1.00	2.30	3.163 (2)	144
C4-H4O2ⁱⁱ	1.00	2.44	3.377 (2)	156
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012); 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: OLEX2 (Dolomanov et al., 2009); 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: ZL2516 ).

Acknowledgements

The authors gratefully acknowledge the National Science Foundation (NSF-CAREER grant to RES, CHE-0846680; NSF-RUI grant to DCF, CHE-0957482). DCF also gratefully acknowledges the Camille and Henry Dreyfus Foundation (TH-06-008) for partial support of this work.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brieger, G. & Nestrick, T. J. (1974). Chem. Rev. 74, 567-580.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Knowles, W. S. (2002). Angew. Chem. Int. Ed. 41, 1998-2007.
Lowry, T. H. & Richardson, K. S. (1987). Mechanism and Theory in Organic Chemistry, 3rd ed. New York: Harper & Row.
Oppolzer, W. (1991). Comprehensive Organic Synthesis, edited by B. M. Trost & I Fleming. Oxford: Pergamon.
Palmer, D. R. J. (2004). J. Chem. Educ. 81, 1633-1635.
Pellissier, H. (2012). Tetrahedron, 68, 2197-2232.
Pindur, U., Lutz, G. & Otto, C. (1993). Chem. Rev. 93, 741-761.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, M. B. (2012). March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th ed. New York: Wiley.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

(1S*,2R*,3S*,4R*,5R*)-5-Tetradecyloxymethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride