2,6-Bis[(4R,5R)-4,5-diphenyl-4,5-di­hydro-1,3-oxazol-2-yl]pyridine

Lin, N.; Deng, Y.-Q.; Chen, M.-M.; Luo, R.-S.; Ng, S.W.

doi:10.1107/S1600536811014668

Volume 67
Part 6
Page o1344
June 2011

Received 17 April 2011
Accepted 19 April 2011
Online 7 May 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.034
wR = 0.099
Data-to-parameter ratio = 7.1
Details

2,6-Bis[(4R,5R)-4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridine

Ning Lin,^a Yan-Qiu Deng,^a Miao-Miao Chen,^a Ren-Shi Luo ^a and Seik Weng Ng ^b ^*

^aInstitute of Drug Synthesis and Pharmaceutical Processes, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The molecule of the title compound, C₃₅H₂₇N₃O₂, lies on a twofold rotation axis passing through the pyridine ring. The five-membered ring is approximately flat (r.m.s. deviation = 0.065 Å) and is essentially coplanar [dihedral angle = 4.2 (2)°] with the pyridine ring.

Related literature

For the synthesis of the precursor, see: Desimoni et al. (2001). For the structure of 2,6-bis(2-oxazolinyl)pyridine, see: Sada et al. (2003).

Experimental

Crystal data

C₃₅H₂₇N₃O₂
M_r = 521.60
Monoclinic, C 2
a = 19.035 (2) Å
b = 6.5908 (7) Å
c = 14.3001 (15) Å
= 129.454 (1)°
V = 1385.2 (3) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.38 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
3266 measured reflections
1299 independent reflections
1190 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.099
S = 1.05
1299 reflections
182 parameters
1 restraint
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.11 e Å^-3
Absolute structure: 768 Friedel pairs merged

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5522 ).

Acknowledgements

The authors thank the Scientific Research Foundation for Returned Overseas Chinese Scholars and the Programme for New Century Excellent Talents (both from the State Education Ministry of China), the Project of International Science and Technology Cooperation (from the Ministry of Science and Technology of China) and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Desimoni, G., Faita, G., Filippone, S., Mella, M., Zampori, M. G. & Zema, M. (2001). Tetrahedron, 57, 10203-10212.
Sada, K., Sugimoto, T., Tani, T., Tateishi, Y., Yi, T., Shinkai, S., Maeda, H., Tohnai, N. & Miyata, M. (2003). Chem. Lett. 32, 758-759.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds