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

Bushra Maliha; Muhammad Ilyas Tariq; M Nawaz Tahir; Ishtiaq Hussain; Muhammad Ali

doi:10.1107/S1600536808040075

. 2008 Dec 6;65(Pt 1):o41. doi: 10.1107/S1600536808040075

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

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

PMCID: PMC2967958 PMID: 21581684

Abstract

In the molecule of the title compound, C₁₁H₁₄N₂O₂S, the five-membered ring adopts an envelope conformation and an intramolecular N—H⋯O hydrogen bond occurs. Intramolecular N—H⋯O, C—H⋯S and C—H⋯N hydrogen bonds result in the formation of two five- and one six-membered rings, having twisted conformations. In the crystal structure, intermolecular N—H⋯O, N—H⋯S and C—H⋯S hydrogen bonds link the molecules, forming polymeric sheets. The π–π 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⋯π 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,
a = 15.4577 (8) Å
b = 8.6455 (5) Å
c = 18.2184 (10) Å
β = 107.322 (2)°
V = 2324.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.110
S = 1.01
2894 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.37 e Å⁻³

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 Material

Crystal structure: contains datablocks text, I. DOI: 10.1107/S1600536808040075/hk2586sup1.cif

e-65-00o41-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040075/hk2586Isup2.hkl

e-65-00o41-Isup2.hkl^{(139.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯O1ⁱ	0.891 (17)	2.087 (17)	2.9738 (14)	172.9 (15)
N2—H2N⋯O1	0.826 (17)	2.413 (17)	2.9867 (14)	127.3 (14)
N2—H2N⋯S1ⁱⁱ	0.826 (17)	2.646 (17)	3.2857 (11)	135.4 (15)
C3—H3⋯S1ⁱⁱⁱ	0.95	2.79	3.7362 (13)	178
C1—H1⋯CgB^iv	0.98	2.500 (17)	3.4059 (13)	155.1 (1)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . CgB is the centroids of the N1/C1/C2/C7/C8 ring.

supplementary crystallographic information

Comment

Isoindoles and their derivatives are of great pharmaceutical importance (Mancilla et al., 2007). Certain derivatives of isoindoles have shown a wide range of herbicidal activities (Toru et al., 1986). The title compound is in continuation of the syntheses of isoindoles along with their derivatives and characterizations with the help of X-ray crystallography (Maliha et al., 2007; Maliha, Hussain et al., 2008; Maliha, Tariq et al., 2008).

In the molecule of title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C2-C7) is, of course, planar, while the five-membered ring B (N1/C1/C2/C7/C8) adopts envelope conformation with C8 atom displaced by 0.141 (3) Å from the plane of the other ring atoms. The intramolecular N-H···O, C-H···S and C-H···N hydrogen bonds (Table 1) result in the formation of two five- and one six-membered rings: C (N1/S1/C8/C11/H8), D (O1/N1/N2/C1/C11/H2N) and E (O1/N1/C1/C9/H9C), respectively, having twisted conformations.

In the crystal structure, intermolecular N-H···O, N-H···S and C-H···S hydrogen bonds (Table 1) link the molecules to form polymeric sheets, in which the orientations of O—CH₃ groups cause to the R and S-configurations at the carbon atoms, C1 and C8, respectively. The behaviour of the O—CH₃ groups are not identical, because only opposite of S-atom is involved in intramolecular H-bonding. The π-π contacts between the isoindole ring systems, CgB—CgBⁱ and CgB—CgAⁱ [symmetry code: (i) -x, y, 1/2 - z, where CgA and CgB are centroids of the rings A (C2-C7) and B (N1/C1/C2/C7/C8)] may further stabilize the structure, with centroid-centroid distances of 3.5883 (8) Å and 4.0619 (8) Å. There also exist two C–H···π interactions (Table 1).

Experimental

For the preparation of the title conpound, ortho-phthaldehyde (1.34 g, 200 mmol) and thiourea (0.76 g, 200 mmol) were added to distilled water (250 ml), and aqueous NaOH (5 ml, 5%) was added dropwise with constant stirring. After 3 h, a colorless precipitate was obtained, which was washed with hexane, ethanol, acetone and methanol, respectively. Then, it was further refluxed in methanol for 2 h, and left to stand overnight. The deep red tiny crystals settled down, which were washed with ether, hexane and cold methanol, respectively. Crystals suitable for X-ray analysis were obtained from a solution of acetone/methanol mixture by slow evaporation at room temperature.