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

Okuda, K.; Hirota, T.; Nishina, Y.; Ishida, H.

doi:10.1107/S1600536812044261

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 (C-C) = 0.002 Å
R = 0.031
wR = 0.079
Data-to-parameter ratio = 20.6
Details

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

Kensuke Okuda,^a ^* Takashi Hirota,^b Yuta Nishina ^c and Hiroyuki Ishida ^d ^*

^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, 2011). For the synthesis of the title compound, see: Okuda et al. (2012).

Experimental

Crystal data

C₁₄H₁₃ClN₂O
M_r = 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 radiation
= 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) T_min = 0.931, T_max = 0.991
17373 measured reflections
3359 independent reflections
3095 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.079
S = 1.05
3359 reflections
163 parameters
1 restraint
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.15 e Å^-3
Absolute structure: Flack (1983), 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-HA	D-H	HA	DA	D-HA
C12-H12BCg1ⁱ	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); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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

organic compounds