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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 [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.108
Data-to-parameter ratio = 15.9
Details
Open access

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

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-H...O 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[Oppolzer, W. (1991). Comprehensive Organic Synthesis, edited by B. M. Trost & I Fleming. Oxford: Pergamon.]); Pindur et al. (1993[Pindur, U., Lutz, G. & Otto, C. (1993). Chem. Rev. 93, 741-761.]). For a review on asymmetric cycloaddion processes, see: Pellissier (2012[Pellissier, H. (2012). Tetrahedron, 68, 2197-2232.]). For a review on catalytic hydrogenations, see: Brieger & Nestrick (1974[Brieger, G. & Nestrick, T. J. (1974). Chem. Rev. 74, 567-580.]). For a review on asymmetric catalytic hydrogenation processes, see: Knowles (2002[Knowles, W. S. (2002). Angew. Chem. Int. Ed. 41, 1998-2007.]). For discussions on reaction mechanisms with specifics on kinetic and thermodynamic control, see: Lowry & Richardson (1987[Lowry, T. H. & Richardson, K. S. (1987). Mechanism and Theory in Organic Chemistry, 3rd ed. New York: Harper & Row.]); Smith (2012[Smith, M. B. (2012). March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th ed. New York: Wiley.]). For a discussion on Diels-Alder selectivity using maleic anhydride, see: Palmer (2004[Palmer, D. R. J. (2004). J. Chem. Educ. 81, 1633-1635.]).

[Scheme 1]

Experimental

Crystal data
  • C23H38O5

  • Mr = 394.53

  • Monoclinic, P 21 /n

  • a = 6.8541 (5) Å

  • b = 35.206 (4) Å

  • c = 9.2992 (7) Å

  • [beta] = 99.060 (7)°

  • V = 2216.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.865, Tmax = 1.000

  • 9120 measured reflections

  • 4053 independent reflections

  • 2974 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.108

  • S = 1.04

  • 4053 reflections

  • 255 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...O1i 1.00 2.30 3.163 (2) 144
C4-H4...O2ii 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [CrossRef] [ChemPort] [ISI]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Knowles, W. S. (2002). Angew. Chem. Int. Ed. 41, 1998-2007.  [CrossRef] [ChemPort]
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.  [CrossRef] [ChemPort]
Pellissier, H. (2012). Tetrahedron, 68, 2197-2232.  [ISI] [CrossRef] [ChemPort]
Pindur, U., Lutz, G. & Otto, C. (1993). Chem. Rev. 93, 741-761.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3374  [ doi:10.1107/S1600536812046259 ]

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