7-Nitro-1,2,3,4-tetra­hydro­naphthalene-1-spiro-2′-(1,3-dithiane)

Fun, H.-K.; Kia, R.; Maity, A.C.; Goswami, S.

doi:10.1107/S1600536809001536

Volume 65
Part 2
Page o347
February 2009

Received 25 December 2008
Accepted 13 January 2009
Online 17 January 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.077
Data-to-parameter ratio = 41.0
Details

7-Nitro-1,2,3,4-tetrahydronaphthalene-1-spiro-2'-(1,3-dithiane)

Hoong-Kun Fun,^a ^* Reza Kia,^a Annada C. Maity ^b and Shyamaprosad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C₁₃H₁₅NO₂S₂, the nitro group is coplanar with the benzene ring to which it is attached, forming a dihedral angle of 1.07 (14)°. The dithiane ring adopts a chair conformation. In the crystal structure, molecules are linked through C-HO and C-H [pi] [CCg = 3.7164 (15) Å] interactions. The crystal studied was an inversion twin with an 0.134 (5):0.866 (5) domain ratio.

Related literature

For the calculation of ring puckering parameters, see: Cremer & Pople (1975). For related literature including applications, see: Goswami & Maity (2008); Fun et al. (2009).

Experimental

Crystal data

C₁₃H₁₅NO₂S₂
M_r = 281.38
Orthorhombic, F d d 2
a = 12.8673 (1) Å
b = 42.2330 (6) Å
c = 9.1819 (1) Å
V = 4989.67 (10) Å³
Z = 16
Mo K radiation
= 0.42 mm^-1
T = 100.0 (1) K
0.41 × 0.30 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.849, T_max = 0.977
54206 measured reflections
6726 independent reflections
5979 reflections with I > 2(I)
R_int = 0.067

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.077
S = 1.06
6726 reflections
164 parameters
1 restraint
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.23 e Å^-3
Absolute structure: Flack (1983), 3202 Friedel pairs
Flack parameter: 0.13 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13AO1ⁱ	0.97	2.58	3.4565 (18)	151
C7-H7ACg1ⁱⁱ	0.93	2.82	3.7164 (15)	162
Symmetry codes: (i) $[-x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 4}}, y+{\script{3\over 4}}, z+{\script{1\over 4}}]$ . Cg1 is the centroid of the C5-C10 benzene ring.

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, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2351 ).

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant (No. 305/PFIZIK/613312). RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. We thank the DST [SR/S1/OC-13/2005], Government of India, for financial support. ACM thanks the UGC, Government of India, for a fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant (No. 1001/PFIZIK/811012).

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Fun, H.-K., Kia, R., Maity, A. C. & Goswami, S. (2009). Acta Cryst. E65, o173.
Goswami, S. & Maity, A. C. (2008). Tetrahedron Lett. 49, 3092-3096.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds