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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 [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.127
Data-to-parameter ratio = 13.3
Details
Open access

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

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-H...O hydrogen bonds.

Related literature

For general background and therapeutic applications of [beta]-lactams, see: Banik & Becker (2000[Banik, B. K. & Becker, F. F. (2000). Tetrahedron Lett. 41, 6551-6554.]); Brakhage (1998[Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547-585.]). For a related structure, see: Sundaramoorthy et al. (2012[Sundaramoorthy, S., Rajesh, R., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o2200-o2201.]).

[Scheme 1]

Experimental

Crystal data
  • C37H34N2O7

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.978

  • 26528 measured reflections

  • 5614 independent reflections

  • 3210 reflections with I > 2[sigma](I)

  • Rint = 0.062

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C33-H33...O4i 0.93 2.49 3.409 (3) 173
C37-H37C...O7ii 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [ChemPort]
Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547-585.  [ISI] [ChemPort] [PubMed]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sundaramoorthy, S., Rajesh, R., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o2200-o2201.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3329-o3330   [ doi:10.1107/S1600536812045795 ]

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