1,3-Dimeth­oxy-2,3-dihydro-1H-isoindole-2-carbothio­amide

Maliha, B.; Tariq, M.I.; Tahir, M.N.; Hussain, I.; Ali, M.

doi:10.1107/S1600536808040075

Volume 65
Part 1
Page o41
January 2009

Received 26 November 2008
Accepted 27 November 2008
Online 6 December 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.110
Data-to-parameter ratio = 15.8
Details

1,3-Dimethoxy-2,3-dihydro-1H-isoindole-2-carbothioamide

Bushra Maliha,^a Muhammad Ilyas Tariq,^b M. Nawaz Tahir,^c ^* Ishtiaq Hussain ^a and Muhammad Ali ^d

^aInstitute of Chemistry, University of the Punjab, Lahore-54590, Pakistan,^bDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan,^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^dDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the molecule of the title compound, C₁₁H₁₄N₂O₂S, the five-membered ring adopts an envelope conformation and an intramolecular N-HO hydrogen bond occurs. Intramolecular N-HO, C-HS and C-HN hydrogen bonds result in the formation of two five- and one six-membered rings, having twisted conformations. In the crystal structure, intermolecular N-HO, N-HS and C-HS hydrogen bonds link the molecules, forming polymeric sheets. The [pi] - [pi] contacts between the isoindole ring systems, [centroid-centroid distances = 3.5883 (8) and 4.0619 (8) Å] may further stabilize the structure. A C-H [pi] interactions also occur.

Related literature

For general background to isoindoles and their derivatives, see: Mancilla et al. (2007); Toru et al. (1986). For related structures, see: Maliha et al. (2007); Maliha, Hussain et al. (2008); Maliha, Tariq et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₄N₂O₂S
M_r = 238.30
Monoclinic, C 2/c
a = 15.4577 (8) Å
b = 8.6455 (5) Å
c = 18.2184 (10) Å
= 107.322 (2)°
V = 2324.3 (2) Å³
Z = 8
Mo K radiation
= 0.27 mm^-1
T = 100 (2) K
0.20 × 0.16 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.945, T_max = 0.969
18083 measured reflections
2894 independent reflections
2471 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.110
S = 1.01
2894 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.44 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1NO1ⁱ	0.891 (17)	2.087 (17)	2.9738 (14)	172.9 (15)
N2-H2NO1	0.826 (17)	2.413 (17)	2.9867 (14)	127.3 (14)
N2-H2NS1ⁱⁱ	0.826 (17)	2.646 (17)	3.2857 (11)	135.4 (15)
C3-H3S1ⁱⁱⁱ	0.95	2.79	3.7362 (13)	178
C1-H1CgB^iv	0.98	2.500 (17)	3.4059 (13)	155.1 (1)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) $[-x, y, -z+{\script{1\over 2}}]$ . CgB is the centroids of the N1/C1/C2/C7/C8 ring.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2586 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. 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.
Maliha, B., Hussain, I., Siddiqui, H. L., Tariq, M. I. & Parvez, M. (2007). Acta Cryst. E63, o4728.
Maliha, B., Hussain, I., Tahir, M. N., Tariq, M. I. & Siddiqui, H. L. (2008). Acta Cryst. E64, o626.
Maliha, B., Tariq, M. I., Tahir, M. N., Hussain, I. & Siddiqui, H. L. (2008). Acta Cryst. E64, o786.
Mancilla, T., Correa-Basurto, J. C., Carbajal, K. S. A., Escalante, E. T. J. S. & Ferrara, J. T. (2007). J. Mex. Chem. Soc. 51, 96-102.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Toru, H., Eiki, N., Ryo, Y. & Shunichi, H. (1986). US Patent No., 4 595 409.

organic compounds