Methyl 12-hydroxy-10-[1-(4-meth­oxy­phen­yl)-2-oxo-3-phen­oxy­azetidin-4-yl]-11-oxa-3-aza­hexa­cyclo­[11.7.1.02,9.02,12.03,7.017,21]henicosa-1(20),13,15,17(21),18-penta­ene-9-carboxyl­ate

Suhitha, S.; Srinivasan, T.; Rajesh, R.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536812045795

Volume 68
Part 12
Pages o3329-o3330
December 2012

Received 31 October 2012
Accepted 6 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.127
Data-to-parameter ratio = 13.3
Details

Methyl 12-hydroxy-10-[1-(4-methoxyphenyl)-2-oxo-3-phenoxyazetidin-4-yl]-11-oxa-3-azahexacyclo[11.7.1.0^2,9.0^2,12.0^3,7.0^17,21]henicosa-1(20),13,15,17(21),18-pentaene-9-carboxylate

Sivasubramanian Suhitha,^a Thothadri Srinivasan,^a Raju Rajesh,^b Raghavachary Raghunathan ^b and Devadasan Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C₃₇H₃₄N₂O₇, both pyrrolidine rings adopt envelope conformations. The [beta] -lactam ring is close to planar (r.m.s. deviation = 0.0395 Å) and makes a dihedral angle of 83.35 (15)° with the furan ring. The O atom attached to the [beta] -lactam ring deviates by 0.187 (2) Å from the mean plane of the ring. The [beta] -lactam ring makes dihedral angles of 14.90 (15) and 27.72 (17)° with the methoxyphenyl and phenyl rings, respectively. The crystal packing features C-HO hydrogen bonds.

Related literature

For general background and therapeutic applications of [beta] -lactams, see: Banik & Becker (2000); Brakhage (1998). For a related structure, see: Sundaramoorthy et al. (2012).

Experimental

Crystal data

C₃₇H₃₄N₂O₇
M_r = 618.66
Orthorhombic, P b c a
a = 9.6545 (11) Å
b = 20.363 (2) Å
c = 31.804 (3) Å
V = 6252.5 (11) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.969, T_max = 0.978
26528 measured reflections
5614 independent reflections
3210 reflections with I > 2(I)
R_int = 0.062

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.127
S = 1.00
5614 reflections
421 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.14 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C33-H33O4ⁱ	0.93	2.49	3.409 (3)	173
C37-H37CO7ⁱⁱ	0.96	2.53	3.217 (3)	128
Symmetry codes: (i) -x, -y, -z+1; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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, 2012); 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: PV2604 ).

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India for the data collection. TS thanks the DST for an Inspire fellowship.

References

Banik, B. K. & Becker, F. F. (2000). Tetrahedron Lett. 41, 6551-6554.
Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547-585.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sundaramoorthy, S., Rajesh, R., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o2200-o2201.