11-Hy­droxy-9-[1-(4-methyl­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-18-oxo-10-oxa-2-aza­penta­cyclo­[9.7.0.01,8.02,6.012,17]octa­deca-12,14,16-triene-8-carbonitrile

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

doi:10.1107/S1600536812044479

Volume 68
Part 12
Pages o3290-o3291
December 2012

Received 12 October 2012
Accepted 26 October 2012
Online 7 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.123
Data-to-parameter ratio = 17.1
Details

11-Hydroxy-9-[1-(4-methylphenyl)-4-oxo-3-phenylazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0^1,8.0^2,6.0^12,17]octadeca-12,14,16-triene-8-carbonitrile

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, C₃₃H₂₉N₃O₅, the four-membered ring of the [beta] -lactam fragment is essentially planar (r.m.s. deviation = 0.0122 Å), with the carbonyl O atom displaced from this ring by 0.856 (9) Å. The mean planes of the methoxyphenyl and phenyl rings are inclined at dihedral angles 85.10 (7) and 21.56 (14)°, respectively, with respect to the mean plane of the four-membered ring. The pyrrolidine rings adopt envelope conformations with C atoms lying 0.535 (4) and 0.519 (4) Å out of the planes formed by the remaining ring atoms. The furan ring also adopts an envelope conformation with a C atom 0.560 (3) Å out of the plane formed by the remaining ring atoms. The nine-membered indene ring is almost planar (r.m.s. deviation = 0.0240 Å), with the carbonyl O atom displaced by 0.145 (3) Å from this ring. The molecular structure is stabilized by a strong intramolecular O-HN hydrogen bond and the crystal structure is consolidated by C-HO hydrogen bonds.

Related literature

For general background to [beta] -lactams, see: Brakhage (1998). For a related structure, see: Sundaramoorthy et al. (2012).

Experimental

Crystal data

C₃₃H₂₉N₃O₅
M_r = 547.59
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.2874 (16) Å
b = 14.138 (3) Å
c = 18.866 (3) Å
V = 2743.9 (8) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.973, T_max = 0.982
14810 measured reflections
6406 independent reflections
4551 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.123
S = 1.00
6406 reflections
375 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10O2ⁱ	0.98	2.43	3.337 (3)	154
C13-H13AO2ⁱ	0.97	2.41	3.321 (3)	156
C29-H29O4ⁱ	0.93	2.55	3.228 (3)	130
O4-H4AN2	0.93 (3)	1.84 (3)	2.602 (3)	137 (3)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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, 1997); 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: PV2596 ).

Acknowledgements

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

References

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. (1997). J. Appl. Cryst. 30, 565.
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.