6′-Bromo-1′H-spiro­[cyclo­hexane-1,2′-pyrido[2,3-d]pyrimidin]-4′(3′H)-one

Yang, L.; Shi, D.; Chen, S.; Chai, H.; Li, J.

doi:10.1107/S1600536811052299

Volume 68
Part 1
Page o178
January 2012

Received 31 October 2011
Accepted 4 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.003 Å
R = 0.035
wR = 0.074
Data-to-parameter ratio = 19.5
Details

6'-Bromo-1'H-spiro[cyclohexane-1,2'-pyrido[2,3-d]pyrimidin]-4'(3'H)-one

Liupan Yang,^a Daxin Shi,^a Shu Chen,^a Hongxin Chai ^a and Jiarong Li ^a ^*

^aSchool of Chemical Engineering and Environment, Beijing Institue of Technology, Beijing 100081, People's Republic of China
Correspondence e-mail: jrli@bit.edu.cn

The title compound, C₁₂H₁₄BrN₃O, is built up from two fused six-membered rings and one six-membered ring linked through a spiro C atom. The hydropyrimidine ring has an envelope conformation and the cyclohexane ring is in a chair conformation. In the crystal, molecules are linked by N-HO and N-HN hydrogen bonds, forming a molecular tape along the b axis.

Related literature

For medicinal and biological properties of 2,3-dihydropyrido[2,3-d]-pyrimidin-4(1H)-one derivatives, see: Parish et al. (1982); Narayana et al. (2009). For related structures, see: Shi et al. (2010); Ling et al. (2009).

Experimental

Crystal data

C₁₂H₁₄BrN₃O
M_r = 296.17
Monoclinic, P 2₁ /c
a = 10.591 (3) Å
b = 12.359 (3) Å
c = 9.116 (3) Å
= 97.951 (4)°
V = 1181.7 (6) Å³
Z = 4
Mo K radiation
= 3.47 mm^-1
T = 153 K
0.40 × 0.24 × 0.09 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009) T_min = 0.324, T_max = 0.732
10128 measured reflections
3160 independent reflections
2283 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.074
S = 1.00
3160 reflections
162 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.55 e Å^-3
_min = -0.66 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NN3ⁱ	0.83 (2)	2.52 (2)	3.337 (2)	169 (2)
N2-H2NO1ⁱⁱ	0.83 (2)	1.98 (2)	2.807 (2)	175 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2009); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku/MSC, 2009); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5001 ).

Acknowledgements

The authors thank Beijing Institute of Technology for the X-ray diffraction analysis.

References

Narayana, B., Rao, A. R. & Rao, P. S. (2009). Eur. J. Med. Chem. 44, 1369-1376.
Ling, Z., Shi, D., Yanqiu, F., Wei, X. & Li, J. (2009). Acta Cryst. E65, o1097.
Parish, H. A. Jr, Gilliom, R. D., Purcell, W. P., Browne, R. K., Spirk, R. F. & White, H. D. (1982). J. Med. Chem. 25, 98-102.
Rigaku/MSC (2009). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shi, D., Yang, L., Tang, J., Wang, X. & Li, J. (2010). Acta Cryst. E66, o2301.

organic compounds