4,9-Dioxa-1,3(1,2)-dibenzena-2(4,5)-1,3-oxazolidinacyclononaphane

Balakrishnan, B.; Seshadri, P.R.; Purushothaman, S.; Raghunathan, R.

doi:10.1107/S1600536810052517

Volume 67
Part 2
Page o469
February 2011

Received 30 November 2010
Accepted 14 December 2010
Online 22 January 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.146
Data-to-parameter ratio = 17.7
Details

4,9-Dioxa-1,3(1,2)-dibenzena-2(4,5)-1,3-oxazolidinacyclononaphane

B. Balakrishnan,^a P. R. Seshadri,^b ^* S. Purushothaman ^c and R. Raghunathan ^c

^aDepartment of Physics, P. T. Lee Chengalvaraya Naicker College of Engineering & Technology, Kancheepuram 631 502, India,^bPostGraduate & Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: seshadri_pr@yahoo.com

The oxazole ring in the title compound, C₂₀H₂₃NO₃, adopts an envelope conformation while the 12-membered ring is in a chair conformation. The dihedral angle between the benzene rings is 37.8 (1)°. The crystal structure displays intermolecular C-HO hydrogen bonding.

Related literature

For general background to cyclophanes and 1,3-dipolar cycloaddition reactions, see: Whelligan et al. (2006); Poornachandran et al. (2008). For the chemistry of azomethine ylides, see; Longeon et al. (1990). For descriptions of ring conformations, see: Cremer & Pople (1975); Nardelli (1983).

Experimental

Crystal data

C₂₀H₂₃NO₃
M_r = 325.39
Monoclinic, P 2₁ /c
a = 9.5193 (7) Å
b = 13.0996 (8) Å
c = 13.6000 (9) Å
= 96.704 (3)°
V = 1684.3 (2) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
33618 measured reflections
3864 independent reflections
2937 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.146
S = 1.02
3864 reflections
218 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C14-H14O1ⁱ	0.93	2.56	3.396 (2)	150
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5428 ).

Acknowledgements

BB thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Longeon, A., Guyot, M. & Vacelet, J. (1990). Experentia, 46, 548-550.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Poornachandran, M. & Raghunathan, R. (2008). Tetrahedron, 64, 6461-6474.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Whelligan, D. K. & Bolm, C. (2006). J. Org. Chem. 71, 4609-4618.

organic compounds

4,9-Dioxa-1,3(1,2)-dibenzena-2(4,5)-1,3-oxazolidinacyclononaphane

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References