Ethyl 1-(4-chloro­phen­yl)-3-[1-(4-meth­oxy­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-2-nitro-2,3,10,10a-tetra­hydro-1H,5H-pyr­rolo[1,2-b]isoquinoline-10a-carboxyl­ate

Sundaresan, S.; Ramesh, P.; Arumugam, N.; Raghunathan, R.; Ponnuswamy, M.N.

doi:10.1107/S1600536808030961

Volume 64
Part 10
Page o2042
October 2008

Received 17 September 2008
Accepted 25 September 2008
Online 30 September 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 13.1
Details

Ethyl 1-(4-chlorophenyl)-3-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-nitro-2,3,10,10a-tetrahydro-1H,5H-pyrrolo[1,2-b]isoquinoline-10a-carboxylate

S. Sundaresan,^a P. Ramesh,^b N. Arumugam,^c R. Raghunathan ^c and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600025, India,^bDepartment of Physics, Presidency College (Autonomous), Chennai 600005, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C₃₇H₃₄ClN₃O₆, the pyrrolidine and piperidine rings adopt envelope and boat conformations, respectively. The [beta] -lactam ring is planar and forms dihedral angles of 21.3 (2) and 73.9 (2)°, respectively, with the attached methoxyphenyl and phenyl rings. Intramolecular C-HO and C-HN hydrogen bonds are observed. Centrosymmetrically related molecules are linked together by weak C-HO hydrogen bonds to form dimers.

Related literature

For the biological properties of [beta] -lactam derivatives, see: Borthwick et al. (1998); Brakhage (1998); Burnett (1994); Han et al. (1995); Vaccaro & Davis (1998); Vaccaro et al. (1998). For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental

Crystal data

C₃₇H₃₄ClN₃O₆
M_r = 652.12
Monoclinic, P 2₁ /n
a = 9.1723 (2) Å
b = 18.0452 (4) Å
c = 19.7475 (5) Å
= 100.638 (1)°
V = 3212.35 (13) Å³
Z = 4
Mo K radiation
= 0.17 mm^-1
T = 293 (2) K
0.22 × 0.20 × 0.17 mm

Data collection

Bruker kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.963, T_max = 0.971
30325 measured reflections
5582 independent reflections
3760 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.135
S = 1.02
5582 reflections
426 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2AN27	0.97	2.53	3.196 (3)	126
C24-H24O3	0.98	2.58	3.186 (3)	121
C25-H25O6ⁱ	0.98	2.60	3.479 (3)	150
C35-H35O5	0.93	2.60	3.157 (3)	119
C40-H40AO4ⁱ	0.96	2.49	3.232 (4)	134
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2676 ).

Acknowledgements

SS thanks Dr Babu Varghese, SAIF, IIT Madras, Chennai, India, for his help with the data collection.

References

Borthwick, A. D., Weingarte, G., Haley, T. M., Tomaszewski, M., Wang, W., Hu, Z., Bedard, J., Jin, H., Yuen, L. & Mansour, T. S. (1998). Bioorg. Med. Chem. Lett. 8, 365-370.
Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547-585.
Bruker (2004). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, D. A. (1994). Tetrahedron Lett. 35, 7339-7342.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Han, W. T., Trehan, A. K., Wright, J. J. K., Federici, M. E., Seiler, S. M. & Meanwell, N. A. (1995). Bioorg. Med. Chem. Lett. 3, 1123-1143.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Vaccaro, W. D. & Davis, H. R. Jr (1998). Bioorg. Med. Chem. Lett. 8, 313-318.
Vaccaro, W. D., Sher, R. & Davis, H. R. Jr (1998). Bioorg. Med. Chem. Lett. 8, 35-40.

organic compounds