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Volume 69 
Part 10 
Page o1570  
October 2013  

Received 21 June 2013
Accepted 7 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.065
Data-to-parameter ratio = 19.0
Details
Open access

Methyl 8-bromo-3-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-1-methyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-3a-carboxylate

aDepartment of Physics, Presidency College, Chennai 600 005, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title compound, C30H29BrN2O5, the [beta]-lactam ring is essentially planar, with the O atom displaced from this plane by 0.856 (9) Å, and forming dihedral angles of 24.35 (13) and 89.42 (14)° with the planes of the benzene substituent groups on this ring. The tetrahydropyran ring adopts an envelope conformation with the C atom bearing the [beta]-lactam ring as the flap. In the crystal, weak C-H...O hydrogen bonds with carboxyl and tetrahydropyran O-atom acceptors give rise to a chain structure extending along the b-axis direction.

Related literature

For general background to [beta]-lactams, see: 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.]). For conformation of the molecular structure, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C30H29BrN2O5

  • Mr = 577.46

  • Monoclinic, P 21

  • a = 10.904 (5) Å

  • b = 10.765 (5) Å

  • c = 11.405 (5) Å

  • [beta] = 91.681 (5)°

  • V = 1338.2 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.58 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2008[Bruker (2008). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.983

  • 28413 measured reflections

  • 6511 independent reflections

  • 5355 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.065

  • S = 0.96

  • 6511 reflections

  • 343 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2910 Friedel pairs

  • Absolute structure parameter: 0.006 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20B...O4i 0.97 2.43 3.366 (3) 161
C14-H14...O5ii 0.93 2.56 3.309 (3) 138
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+2]; (ii) [-x, y+{\script{1\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2008[Bruker (2008). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: 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: ZS2268 ).


Acknowledgements

SA thanks the UGC-India for financial support.

References

Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547-585.  [Web of Science] [ChemPort] [PubMed]
Bruker (2008). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sundaramoorthy, S., Rajesh, R., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o2200-o2201.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1570  [ doi:10.1107/S1600536813024963 ]

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