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Volume 69 
Part 5 
Pages o706-o707  
May 2013  

Received 31 March 2013
Accepted 3 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.048
wR = 0.144
Data-to-parameter ratio = 14.6
Details
Open access

Ethyl 3-(4-chlorobenzoyl)-1-(4-chlorobenzyl)-4-(4-chlorophenyl)-2,2-dioxo-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]thiazine-1-carboxylate

aDepartment of Physics, Sri Subramanya College of Engineering & Technology, Palani 624 615, India,bDepartment of Physics, University College of Engineering, Nagercoil, Anna University, Tirunelveli Region, Nagercoil 629 004, India,cDepartment of Physics, Kalasalingam University, Krishnan Koil 626 190, India, and dDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
Correspondence e-mail: athi81s@yahoo.co.in

In the title compound, C30H28Cl3NO5S, the pyrrolidine ring adopts an envelope conformation (with the N atom as the flap) and the thiazine ring is in a distorted chair conformation. The molecular structure shows three intramolecular C-H...O interactions leading to self-associated ring S(6) and two S(7) motifs. In the crystal, the molecules are linked by C-H...O and C-H...Cl interactions. Two R22(10) and one R22(16) centrosymmetrically related ring motifs are observed in the unit cell and they are connected through C(6) and C(11) chain motifs extending along the b and c axes, respectively.

Related literature

For the biological and pharmacological properties of thiazine, pyrrolidine and pyrrolothiazine compounds, see: Armenise et al. (1991[Armenise, D., Trapani, G., Arrivo, V. & Morlacchi, F. (1991). Il Farmaco, 46, 1023-1032.], 1998[Armenise, D., Trapani, G., Stasi, F. & Morlacchi, F. (1998). Arch. Pharm. 331, 54-58.]); Hemming & Patel (2004[Hemming, K. & Patel, N. (2004). Tetrahedron Lett. 45, 7553-7556.]); Koketsu et al. (2002[Koketsu, M., Tanaka, K., Takenaka, Y., Kwong, C. D. & Ishihara, H. (2002). Eur. J. Pharm. Sci. 15, 307-310.]); Kueh et al. (2003[Kueh, A. J., Marriott, P. J., Wynne, P. M. & Vine, J. H. (2003). J. Chromatogr. A, 1000, 109-124.]); Moriyama et al. (2004[Moriyama, H., Tsukida, T., Inoue, Y., Yokota, K., Yoshino, K., Kondo, H., Miura, N. & Nishimura, S. (2004). J. Med. Chem. 47, 1930-1938.]). For ring puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bonding interactions, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.]). For ring and chain motifs,see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C30H28Cl3NO5S

  • Mr = 620.94

  • Monoclinic, P 21 /c

  • a = 14.0476 (8) Å

  • b = 17.1365 (9) Å

  • c = 13.8230 (8) Å

  • [beta] = 115.893 (1)°

  • V = 2993.5 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.42 mm-1

  • T = 293 K

  • 0.25 × 0.21 × 0.19 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 28492 measured reflections

  • 5280 independent reflections

  • 4593 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.144

  • S = 1.04

  • 5280 reflections

  • 362 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.62 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6B...O41 0.97 2.38 3.051 (3) 126
C37-H37...O2 0.93 2.53 3.213 (3) 131
C50-H50...O41 0.93 2.58 3.282 (4) 132
C6-H6A...O3i 0.97 2.70 3.582 (3) 151
C5-H5...O1i 0.98 2.51 3.320 (3) 140
C8-H8B...Cl3ii 0.97 2.86 3.678 (3) 143
C36-H36...O3iii 0.93 2.65 3.557 (3) 166
C42-H42B...O42iv 0.97 2.61 3.478 (5) 148
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL/PC; molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL/PC.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5304 ).


Acknowledgements

AC and SAB sincerely thank the Vice-Chancellor and Management of Kalasalingam University, Anand Nagar, Krishnan Koil, for their support and encouragement.

References

Armenise, D., Trapani, G., Arrivo, V. & Morlacchi, F. (1991). Il Farmaco, 46, 1023-1032.  [PubMed] [ChemPort]
Armenise, D., Trapani, G., Stasi, F. & Morlacchi, F. (1998). Arch. Pharm. 331, 54-58.  [CrossRef] [ChemPort]
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Hemming, K. & Patel, N. (2004). Tetrahedron Lett. 45, 7553-7556.  [ISI] [CrossRef] [ChemPort]
Koketsu, M., Tanaka, K., Takenaka, Y., Kwong, C. D. & Ishihara, H. (2002). Eur. J. Pharm. Sci. 15, 307-310.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kueh, A. J., Marriott, P. J., Wynne, P. M. & Vine, J. H. (2003). J. Chromatogr. A, 1000, 109-124.  [ISI] [CrossRef] [PubMed] [ChemPort]
Moriyama, H., Tsukida, T., Inoue, Y., Yokota, K., Yoshino, K., Kondo, H., Miura, N. & Nishimura, S. (2004). J. Med. Chem. 47, 1930-1938.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o706-o707   [ doi:10.1107/S1600536813009148 ]

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