(IUCr) Methyl 3-(2-chlorophenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitropyrrolidine-2-carboxylate

Volume 64
Part 6
Pages o1070-o1071
June 2008

Received 1 May 2008
Accepted 7 May 2008
Online 14 May 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.067
wR = 0.317
Data-to-parameter ratio = 12.8
Details

Methyl 3-(2-chlorophenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitropyrrolidine-2-carboxylate

S. Nirmala,^a E. Theboral Sugi Kamala,^a L. Sudha,^b ^* N. Arumugam ^c and R. Raghunathan ^c

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India,^bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
Correspondence e-mail: sudharose18@gmail.com

In the molecule of the title compound, C₃₇H₃₃ClN₄O₆, the four-membered -lactam ring is essentially planar and is oriented at dihedral angles of 30.0 (1), 76.3 (1) and 30.9 (1)° with respect to the methoxyphenyl ring, the phenyl ring and the indole unit, respectively. The pyrrolidine ring adopts a twist conformation. Intramolecular C-HCl and C-HO hydrogen bonds result in the formation of two five- and one six-membered rings. In the crystal structure, intermolecular C-HO and N-HO hydrogen bonds link the molecules. A weak [pi] [pi] interaction between the pyrrole rings further stabilizes the structure, with a centroid-centroid distance of 3.806 (2) Å.

Related literature

For general background, see: Bruggink (2001); Morin & Gorman (1982); Katritzky et al. (1996); Georg (1993); Coyne et al. (2007); Dobrowolski et al. (2004); Cha et al. (2006). For related literature, see: Bhaskaran et al. (2006); Kamala et al. (2008); Ülkü et al. (1997). For ring puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1995).

Experimental

Crystal data

C₃₇H₃₃ClN₄O₆
M_r = 665.12
Triclinic, $[P \overline 1]$
a = 10.399 (3) Å
b = 12.500 (3) Å
c = 14.211 (3) Å
= 93.766 (6)°
= 99.962 (6)°
= 114.066 (5)°
V = 1642.1 (7) Å³
Z = 2
Mo K radiation
= 0.17 mm^-1
T = 293 (2) K
0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX2 CCD diffractometer
Absorption correction: multi-scan (Blessing, 1995) T_min = 0.951, T_max = 0.973
25481 measured reflections
5563 independent reflections
3770 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.317
S = 1.10
5563 reflections
433 parameters
H-atom parameters constrained
_max = 0.51 e Å^-3
_min = -0.64 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11Cl1	0.98	2.57	3.095 (4)	114
C11-H11O3	0.98	2.37	2.786 (4)	105
C22-H22O5	0.93	2.59	3.080 (6)	113
C14-H14O4ⁱ	0.98	2.53	3.443 (5)	154
C34-H34O4ⁱⁱ	0.93	2.59	3.414 (6)	148
N1-H1AO6ⁱⁱⁱ	0.86	2.14	2.982 (5)	167
Symmetry codes: (i) -x, -y, -z; (ii) -x, -y+1, -z; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2460 ).

Acknowledgements

SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions. SN thanks SRM management, India, for their support.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Bhaskaran, S., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Arumugam, N. & Raghunathan, R. (2006). Anal. Sci. 22, x57-x58.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Bruggink, A. (2001). Synthesis of -Lactam Antibiotics, Chemistry, Biocatalysis and Process Integration, edited by A. Bruggink. Dordrecht: Kluwer.
Bruker (2004). APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cha, J. M., Yang, S. & Carlson, K. H. (2006). J. Chromatogr. A, 1115, 46-57.
Coyne, A. G., Muller-Bunz, H. & Guiry, P. J. (2007). Tetrahedron Asymmetry, 18, 199-207.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Dobrowolski, J. C., Sadlej, J. & Mazurek, A. P. (2004). J. Mol. Struct. THEOCHEM, 684, 181-186.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Georg, G. I. (1993). The Organic Chemistry of -Lactams, edited by G. I. Georg. New York: VCH.
Kamala, E. T. S., Nirmala, S., Sudha, L., Arumugam, N. & Raghunathan, R. (2008). Acta Cryst. E64, o716-o717.
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). Comprehensive Heterocyclic Chemistry II, edited by A. R. Katritzky, C. W. Rees & E. F. V. Scriven, Vol. 1b, chs. 1.18-1.20. New York: Elsevier.
Morin, M. B. & Gorman, M. (1982). Chemistry and Biology of -Lactam Antibiotics, edited by M. B. Morin & M. Gorman, pp. 1- 3. New York: Academic Press.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Ülkü, D., Ercan, F. & Güner, V. (1997). Acta Cryst. C53, 1945-1947.

organic compounds