Methyl 4′-isobutyl-2,2′-dimethyl-1,3-dioxo-2,3-dihydro-1H,4′H-spiro­[iso­quinoline-4,5′-oxazole]-4′-carboxyl­ate

Fun, H.-K.; Quah, C.K.; Xu, K.; Zhang, Y.

doi:10.1107/S1600536811019003

Volume 67
Part 6
Pages o1519-o1520
June 2011

Received 10 May 2011
Accepted 19 May 2011
Online 25 May 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.039
wR = 0.113
Data-to-parameter ratio = 26.0
Details

Methyl 4'-isobutyl-2,2'-dimethyl-1,3-dioxo-2,3-dihydro-1H,4'H-spiro[isoquinoline-4,5'-oxazole]-4'-carboxylate

Hoong-Kun Fun,^a ^*⁺ Ching Kheng Quah,^a ⁺⁺ Kai Xu ^b and Yan Zhang ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, People's Republic of China
Correspondence e-mail: hkfun@usm.my

In the isoquinoline ring system of the title molecule, C₁₉H₂₂N₂O₅, the N-heterocyclic ring is in a half-boat conformation. The dioxa-2-azaspiro ring is essentially planar [maximum deviation = 0.042 (1) Å] and forms a dihedral angle of 81.85 (4)° with the benzene ring. In the crystal, the molecules are linked via intermolecular C-HO hydrogen bonds into chains along [010].

Related literature

For general background to and the potential biological activity of the title compound, see: Pollers-Wieers et al. (1981); Malamas et al. (1994); Yu et al. (2010); Mitchell et al. (1995, 2000); Badillo et al. (2010); Wang et al. (2010); Nair et al. (2002); Huang et al. (2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For related structures, see: Fun et al. (2011a,b,c,d).

Experimental

Crystal data

C₁₉H₂₂N₂O₅
M_r = 358.39
Triclinic, $[P \overline 1]$
a = 8.6764 (1) Å
b = 8.9366 (1) Å
c = 12.0684 (2) Å
= 93.495 (1)°
= 109.892 (1)°
= 98.426 (1)°
V = 864.22 (2) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 100 K
0.40 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.961, T_max = 0.982
25638 measured reflections
6231 independent reflections
5381 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.113
S = 1.05
6231 reflections
240 parameters
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2AO4ⁱ	0.93	2.56	3.4353 (11)	158
C4-H4AO2ⁱⁱ	0.93	2.56	3.2878 (11)	136
C12-H12CO4ⁱ	0.96	2.59	3.3600 (11)	138
Symmetry codes: (i) -x+2, -y, -z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2597 ).

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). Financial support from the Program for New Century Excellent Talents in Universities (NCET-08-0271) of China is also acknowledged.

References

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