4-Imino-2,7-dimethyl-5,6,7,8-tetra­hydro-4H-1-benzothieno[2,3-d]pyrimidin-3-amine

Kalashetti, M.B.; Fathima, N.; Khan, A.Y.; Begum, N.S.; Khazi, I.M.

doi:10.1107/S1600536812031893

Volume 68
Part 8
Page o2468
August 2012

Received 5 July 2012
Accepted 12 July 2012
Online 18 July 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.038
wR = 0.112
Data-to-parameter ratio = 14.4
Details

4-Imino-2,7-dimethyl-5,6,7,8-tetrahydro-4H-1-benzothieno[2,3-d]pyrimidin-3-amine

Mallikarjun B. Kalashetti,^a Nikhath Fathima,^b Ashraf Y. Khan,^a Noor Shahina Begum ^b and I. M. Khazi ^a ^*

^aDepartment of Chemistry, Karnatak University, Dharwad 580 003, India, and ^bDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, India
Correspondence e-mail: dr_imk@yahoo.com

In the title compound, C₁₂H₁₆N₄S, the fused benzothiophene and the pyrimidine rings are coplanar [dihedral angle = 1.61 (6)°]. Three C atoms of the cyclohexene ring (at positions 3, 6 and 7) are disordered over two sites with an occupancy ratio of 0.702 (8):0.298 (8). The cyclohexene ring in both the major and minor components adopts a half-chair conformation. The crystal structure is stabilized by N-HN and C-HN interactions, resulting in the formation of inversion dimers with R₂²(10) and R₂²(12) graph-set motifs.

Related literature

For the biological activity of thiophenes, benzothiophenes and pyrimidines, see: Pathak et al. (1991); Shishoo & Jain (1992). For a related crystal structure, see: Panchamukhi et al. (2011). For graph-set notations, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₂H₁₆N₄S
M_r = 248.35
Triclinic, $[P \overline 1]$
a = 6.7514 (5) Å
b = 8.7139 (6) Å
c = 11.8309 (9) Å
= 97.221 (4)°
= 102.820 (4)°
= 112.482 (3)°
V = 609.73 (8) Å³
Z = 2
Mo K radiation
= 0.25 mm^-1
T = 296 K
0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 0.957, T_max = 0.961
11883 measured reflections
2641 independent reflections
2378 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.112
S = 1.08
2641 reflections
184 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3BN4ⁱ	0.89	2.40	3.117 (2)	137
C5-H5BN4ⁱⁱ	0.96	2.67	3.587 (2)	160
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y, -z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2567 ).

Acknowledgements

IMK is thankful to the University Grants Commission, India, for financial assistance.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Panchamukhi, S. I., Fathima, N., Khazi, I. M. & Begum, N. S. (2011). Acta Cryst. E67, o777-o778.
Pathak, U. S., Singh, S. & Padh, J. (1991). Indian J. Chem. Sect. B, 30, 618-619.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shishoo, C. J. & Jain, K. S. J. (1992). J. Heterocycl. Chem. 29, 883-893.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.

organic compounds