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Volume 69 
Part 3 
Pages o438-o439  
March 2013  

Received 8 February 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.127
Data-to-parameter ratio = 18.5
Details
Open access

Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.01,8.02,6.012,17]octadeca-12(17),13,15-triene-8-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, C34H32N2O7, the furan ring adopts a twist conformation and both the pyrrolidine rings adopt envelope conformations with O and C as flap atoms. The [beta]-lactam ring makes a dihedral angles of 80.20 (10)° with the furan ring, of 75.55 (10)° with the pyrrolidine ring, of 12.26 (10)° with the methoxyphenyl ring and of 73.77 (13)° with the phenyl ring. The O atom attached to the [beta]-lactam ring deviates by 0.0385 (13) Å from the ring plane. The molecular conformation is stabilized by intramolecular O-H...N and C-H...O hydrogen bonds. The packing of the crystal is stabilized by intermolecular C-H...O hydrogen bonds, which form a chain running along the b axis.

Related literature

For general background to [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
  • C34H32N2O7

  • Mr = 580.62

  • Monoclinic, P 21 /c

  • a = 10.9030 (5) Å

  • b = 11.8792 (5) Å

  • c = 22.4457 (10) Å

  • [beta] = 93.963 (3)°

  • V = 2900.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 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 = 0.973, Tmax = 0.982

  • 28525 measured reflections

  • 7293 independent reflections

  • 4952 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.127

  • S = 1.02

  • 7293 reflections

  • 394 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 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
O4-H4A...N2 0.91 (2) 1.95 (2) 2.6120 (16) 127.8 (19)
C6-H6...O1 0.93 2.51 3.122 (2) 124
C8-H8...O1i 0.98 2.52 3.4047 (19) 151
C28-H28A...O4ii 0.97 2.58 3.5069 (19) 161
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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 for Windows (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: BT6889 ).


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 and SS thanks the UGC for a meritorious 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 (2013). E69, o438-o439   [ doi:10.1107/S1600536813004789 ]

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