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Volume 68 
Part 12 
Page o3360  
December 2012  

Received 17 September 2012
Accepted 9 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.083
Data-to-parameter ratio = 15.7
Details
Open access

Methyl 2-(2,3,5-trimethyl-1,1-dioxo-2H-1[lambda]6,2,6-thiadiazin-4-yl)benzoate

aChemistry Department, JJT University, Rajasthan, India,bSchool of Chemistry & Physics, University of KwaZulu-Natal, Durban 4000, South Africa,cDepartment of Chemistry, Government Science College, Gandhinagar, Gujarat, India, and dSchool of Pharmacology, University of KwaZulu Natal, Westville Campus, Private Bag X54001, South Africa
Correspondence e-mail: maguireg@ukzn.ac.za

There are two molecules, A and B, in the asymmetric unit of the title compound, C14H16N2O4S, which is the first example reported in this family of compounds in which the Nsp3 atom of the thiadiazine ring is methylated. The thiadiazine rings adopt shallow envelope conformations, with the S atoms displaced by 0.319 (12) and 0.182 (12) Å from the mean planes of the other ring atoms in molecules A and B, respectively. The dihedral angles between the thiadiazine mean planes (excluding S) and the attached benzene rings are 86.8 (3) and 86.7 (3)° for molecules A and B, respectively.

Related literature

For synthetic background, see: Wright (1964[Wright, J. B. (1964). J. Org. Chem. 29, 1905-1909.]). For a related structure, see: Bhatt et al. (2012[Bhatt, N., Bhatt, P., Vyas, K. B., Nimavat, K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2012). Acta Cryst. E68, o2160.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16N2O4S

  • Mr = 308.35

  • Orthorhombic, P n a 21

  • a = 13.5954 (3) Å

  • b = 8.0683 (2) Å

  • c = 25.9554 (7) Å

  • V = 2847.09 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 173 K

  • 0.28 × 0.22 × 0.21 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.935, Tmax = 0.950

  • 33574 measured reflections

  • 6094 independent reflections

  • 4522 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.083

  • S = 0.99

  • 6094 reflections

  • 388 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2751 Friedel pairs

  • Flack parameter: -0.06 (5)

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6962 ).


Acknowledgements

The authors wish to thank Dr Hong Su from the University of Cape Town for assistance with the data collection and refinement.

References

Bhatt, N., Bhatt, P., Vyas, K. B., Nimavat, K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2012). Acta Cryst. E68, o2160.  [CSD] [CrossRef] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wright, J. B. (1964). J. Org. Chem. 29, 1905-1909.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3360  [ doi:10.1107/S1600536812046375 ]

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