2′-Methyl-3,5-diphenyl­spiro­[4,6-dioxa-2-aza­bicyclo­[3.2.0]hept-2-ene-7,4′-iso­quinoline]-1′,3′(2′H,4′H)-dione

Fun, H.-K.; Goh, J.H.; Yu, H.; Zhang, Y.

doi:10.1107/S1600536810008718

Volume 66
Part 4
Pages o803-o804
April 2010

Received 3 March 2010
Accepted 8 March 2010
Online 13 March 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.047
wR = 0.150
Data-to-parameter ratio = 9.2
Details

2'-Methyl-3,5-diphenylspiro[4,6-dioxa-2-azabicyclo[3.2.0]hept-2-ene-7,4'-isoquinoline]-1',3'(2'H,4'H)-dione

Hoong-Kun Fun,^a ^*⁺ Jia Hao Goh,^a ⁺⁺ Haitao Yu ^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 title compound, C₂₅H₁₈N₂O₄, the tetrahydropyridine ring adopts a distorted envelope conformation with the spiro C atom at the flap position [deviation = 0.470 (2) Å]. The dihydro-oxazole ring is planar (r.m.s. deviation = 0.013 Å) and it makes dihedral angles of 73.43 (8) and 4.24 (8)° with the two attached phenyl rings. The dihedral angle between oxetane and oxazole planes is 67.44 (9)°. In the crystal structure, C-HO hydrogen bonds link neighbouring molecules into zigzag chains along the b axis and these chains are linked via C-H [pi] interactions.

Related literature

For general background to and applications of isoquinolinedione derivatives, see: Hall et al. (1994); Malamas & Hohman (1994); Nan et al. (2004). For ring conformations, see: Cremer & Pople (1975). For related structures, see: Fun et al. (2010); Wang et al. (2000). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₅H₁₈N₂O₄
M_r = 410.41
Monoclinic, P 2₁ /c
a = 13.3142 (3) Å
b = 8.0366 (2) Å
c = 19.1913 (5) Å
= 109.882 (1)°
V = 1931.09 (8) Å³
Z = 4
Cu K radiation
= 0.79 mm^-1
T = 100 K
0.27 × 0.26 × 0.25 mm

Data collection

Bruker SMART APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.815, T_max = 0.830
32042 measured reflections
3254 independent reflections
3227 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.150
S = 1.35
3254 reflections
353 parameters
All H-atom parameters refined
_max = 0.80 e Å^-3
_min = -0.88 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13-C18 benzene ring.

D-HA	D-H	HA	DA	D-HA
C17-H17AO1ⁱ	0.97 (2)	2.51 (2)	3.213 (2)	129 (1)
C23-H23ACg1ⁱⁱ	0.96 (2)	2.66 (2)	3.5904 (18)	166 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y-{\script{3\over 2}}, z-{\script{3\over 2}}]$ .

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: CI5051 ).

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). Financial support from the Ministry of Science and Technology of China of the Austria-China Cooperation project (grant No. 2007DFA41590) is acknowledged. JHG also thanks USM for the award of a USM fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Fun, H.-K., Goh, J. H., Yu, H. & Zhang, Y. (2010). Acta Cryst. E66, o724-o725.
Hall, I. H., Chapman, J. M. & Wong, O. T. (1994). Anticancer Drugs, 5, 75-82.
Malamas, M. S. & Hohman, T. C. (1994). J. Med. Chem. 37, 2043-2058.
Nan, F. J., Li, J., Chen, Y. H., Zhang, Y. H., Gu, M. & Zhang, H. J. (2004). PCT Int. Appl. WO 2004111010 A1.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, X.-L., Tian, J.-Z., Ling, K.-Q. & Xu, J.-H. (2000). Res. Chem. Intermed. 26, 679-689.

organic compounds