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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 [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.074
Data-to-parameter ratio = 19.5
Details
Open access

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

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-H...O and N-H...N 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[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.]); Narayana et al. (2009[Narayana, B., Rao, A. R. & Rao, P. S. (2009). Eur. J. Med. Chem. 44, 1369-1376.]). For related structures, see: Shi et al. (2010[Shi, D., Yang, L., Tang, J., Wang, X. & Li, J. (2010). Acta Cryst. E66, o2301.]); Ling et al. (2009[Ling, Z., Shi, D., Yanqiu, F., Wei, X. & Li, J. (2009). Acta Cryst. E65, o1097.]).

[Scheme 1]

Experimental

Crystal data
  • C12H14BrN3O

  • Mr = 296.17

  • Monoclinic, P 21 /c

  • a = 10.591 (3) Å

  • b = 12.359 (3) Å

  • c = 9.116 (3) Å

  • [beta] = 97.951 (4)°

  • V = 1181.7 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku/MSC (2009). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.324, Tmax = 0.732

  • 10128 measured reflections

  • 3160 independent reflections

  • 2283 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.66 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...N3i 0.83 (2) 2.52 (2) 3.337 (2) 169 (2)
N2-H2N...O1ii 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[Rigaku/MSC (2009). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); 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.  [PubMed]
Ling, Z., Shi, D., Yanqiu, F., Wei, X. & Li, J. (2009). Acta Cryst. E65, o1097.  [CSD] [CrossRef] [details]
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.  [CrossRef] [ChemPort] [PubMed]
Rigaku/MSC (2009). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shi, D., Yang, L., Tang, J., Wang, X. & Li, J. (2010). Acta Cryst. E66, o2301.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o178  [ doi:10.1107/S1600536811052299 ]

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