N,N-Bis(2,6-difluoro­benz­yl)-1,3,4-thia­diazol-2-amine

Fun, H.-K.; Liew, W.-C.; Chandrakantha, B.; Isloor, A.M.

doi:10.1107/S1600536809031675

Volume 65
Part 9
Pages o2166-o2167
September 2009

Received 11 August 2009
Accepted 11 August 2009
Online 15 August 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.076
Data-to-parameter ratio = 22.0
Details

N,N-Bis(2,6-difluorobenzyl)-1,3,4-thiadiazol-2-amine

Hoong-Kun Fun,^a ^*⁺ Wei-Ching Liew,^a B. Chandrakantha ^b and Arun M. Isloor ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bSyngene International Ltd, Biocon Park, Plot Nos. 2 & 3, Bommasandra 4th Phase, Jigani Link Rd, Bangalore 560 100, India, and ^cDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C₁₆H₁₁F₄N₃S, the dihedral angles between the thiadiazole ring and the difluorobenzyl rings are 81.95 (7) and 81.96 (7)°, whereas the dihedral angle between the difluorobenzyl rings is 11.41 (7)°. In the crystal structure, C-HN and C-HF interactions link the molecules into two-dimensional arrays parallel to the bc plane.

Related literature

For the synthesis of pharmaceutically condensed heterocyclic thiadiazole derivatives as antimicrobials, see: Swamy et al. (2006). For the synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activity of some new acetic acid derivatives, see: Amir & Shikha (2004). For new bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents, see: Holla et al. (2002). For the synthesis and biological evaluation of thiadiazole derivatives as a novel class of potential anti-tumor agents, see: Ibrahim (2009). For related structures, see: Wang et al. (2009a,b); Yin et al. (2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₆H₁₁F₄N₃S
M_r = 353.34
Orthorhombic, P c a 2₁
a = 32.6678 (6) Å
b = 5.8515 (1) Å
c = 7.8140 (2) Å
V = 1493.69 (5) Å³
Z = 4
Mo K radiation
= 0.26 mm^-1
T = 100 K
0.46 × 0.33 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.887, T_max = 0.965
17980 measured reflections
4796 independent reflections
4299 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.076
S = 1.02
4796 reflections
218 parameters
1 restraint
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.26 e Å^-3
Absolute structure: Flack (1983), 1935 Friedel pairs
Flack parameter: 0.20 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1AN1ⁱ	0.93	2.58	3.392 (2)	146
C3-H3BF3ⁱⁱ	0.97	2.47	3.0226 (16)	116
C8-H8AF4ⁱⁱⁱ	0.93	2.54	3.144 (2)	123
C10-H10BN2^iv	0.97	2.56	3.4191 (17)	148
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) x, y-1, z+1; (iv) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2527 ).

Acknowledgements

HKF and WCL thank Universiti Sains Malaysia (USM) for a Research University Golden Goose Grant (No. 1001/PFIZIK/811012). WCL thanks USM for a USM Fellowship. AMI is grateful to the Director, NITK Surathkal, India, for providing research facilities.

References

Amir, M. & Shikha, K. (2004). Eur. J. Med. Chem. 39, 535-545.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Holla, B. S., Poorjary, K. N., Rao, B. S. & Shivananda, M. K. (2002). Eur. J. Med. Chem. 37, 511-517.
Ibrahim, D. A. (2009). Eur. J. Med. Chem. 44, 2776-2781.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Swamy, S. N., Basappa, B. S., Prabhuswamy, P. B., Doreswamy, B. H., Prasad, J. S. & Rangappa, K. S. (2006). Eur. J. Med. Chem. 41, 531-538.
Wang, Y., Wan, R., Han, F. & Wang, P. (2009a). Acta Cryst. E65, o1425.
Wang, Y., Wan, R., Han, F. & Wang, P. (2009b). Acta Cryst. E65, o1761.
Yin, L.-H., Wan, R., Wang, Y., Han, F. & Wang, J.-T. (2008). Acta Cryst. E64, o1884.

organic compounds