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Volume 68 
Part 11 
Page o3252  
November 2012  

Received 14 October 2012
Accepted 25 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.079
Data-to-parameter ratio = 20.6
Details
Open access

10'-Chloro-3',4'-dihydro-2'H-spiro[cyclopropane-1,7'(6'H)-pyrimido[2,1-a]isoquinolin]-6'-one

aLaboratory of Medicinal and Pharmaceutical Chemistry, Gifu Pharmaceutical University, Gifu 501-1196, Japan,bLaboratory of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Okayama University, Okayama 700-8530, Japan,cResearch Core for Interdisciplinary Sciences, Okayama University, Okayama 700-8530, Japan, and dDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
Correspondence e-mail: okuda@gifu-pu.ac.jp, ishidah@cc.okayama-u.ac.jp

In the title compound, C14H13ClN2O, the fused hydropyrimidine ring adopts an envelope conformation with one of the methylene C atoms at the flap. The three-membered ring is approximately perpendicular to the attached isoquinoline ring system, with a dihedral angle of 89.44 (11)°. In the crystal, molecules are linked by a weak C-H...[pi] interaction, forming a helical chain along the c axis.

Related literature

For recent reports on the development of complex heterocyclic skeletons for potential pharmaceutics in one step using the Truce-Smiles rearrangement, see: Okuda et al. (2010[Okuda, K., Yoshida, M., Hirota, T. & Sasaki, K. (2010). Chem. Pharm. Bull. 58, 363-368.], 2011[Okuda, K., Takechi, H., Hirota, T. & Sasaki, K. (2011). Heterocycles, 83, 1315-1328.]). For the synthesis of the title compound, see: Okuda et al. (2012[Okuda, K., Yoshida, M., Hirota, T. & Sasaki, K. (2012). Synth. Commun. 42, 865-871.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13ClN2O

  • Mr = 260.72

  • Orthorhombic, P c a 21

  • a = 8.8746 (5) Å

  • b = 13.3273 (7) Å

  • c = 9.8331 (6) Å

  • V = 1163.01 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 180 K

  • 0.25 × 0.21 × 0.03 mm

Data collection
  • Rigaku R-AXIS RAPIDII diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.931, Tmax = 0.991

  • 17373 measured reflections

  • 3359 independent reflections

  • 3095 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.079

  • S = 1.05

  • 3359 reflections

  • 163 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1571 Friedel pairs

  • Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/N1/C2-C4/C9 ring.

D-H...A D-H H...A D...A D-H...A
C12-H12B...Cg1i 0.99 2.72 3.6000 (15) 148
Symmetry code: (i) [-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}].

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004[Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2085 ).


References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Okuda, K., Takechi, H., Hirota, T. & Sasaki, K. (2011). Heterocycles, 83, 1315-1328.  [CrossRef] [ChemPort]
Okuda, K., Yoshida, M., Hirota, T. & Sasaki, K. (2010). Chem. Pharm. Bull. 58, 363-368.  [CrossRef] [ChemPort] [PubMed]
Okuda, K., Yoshida, M., Hirota, T. & Sasaki, K. (2012). Synth. Commun. 42, 865-871.  [CrossRef] [ChemPort]
Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3252  [ doi:10.1107/S1600536812044261 ]

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