Methyl 2-(2,3,5-trimethyl-1,1-dioxo-2H-1λ6,2,6-thia­diazin-4-yl)benzoate

Bhatt, N.; Bhatt, P.; Nimavat, K.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536812046375

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 (C-C) = 0.003 Å
R = 0.037
wR = 0.083
Data-to-parameter ratio = 15.7
Details

Methyl 2-(2,3,5-trimethyl-1,1-dioxo-2H-1⁶,2,6-thiadiazin-4-yl)benzoate

Nilay Bhatt,^a Pralav Bhatt,^b Kiran Nimavat,^c Thavendran Govender,^d Hendrik G. Kruger ^b and Glenn E. M. Maguire ^b ^*

^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). For a related structure, see: Bhatt et al. (2012). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₄H₁₆N₂O₄S
M_r = 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 radiation
= 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) T_min = 0.935, T_max = 0.950
33574 measured reflections
6094 independent reflections
4522 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.083
S = 0.99
6094 reflections
388 parameters
1 restraint
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.25 e Å^-3
Absolute structure: Flack (1983), 2751 Friedel pairs
Flack parameter: -0.06 (5)

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); 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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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.
Wright, J. B. (1964). J. Org. Chem. 29, 1905-1909.

organic compounds

Methyl 2-(2,3,5-trimethyl-1,1-dioxo-2H-16,2,6-thiadiazin-4-yl)benzoate