N-Methyl-1-oxoisoindoline-2-carboxamide monohydrate

Bushra Maliha; Muhammad Ilyas Tariq; M Nawaz Tahir; Ishtiaq Hussain; Hamid Latif Siddiqui

doi:10.1107/S1600536808008362

. 2008 Apr 2;64(Pt 5):o786. doi: 10.1107/S1600536808008362

N-Methyl-1-oxoisoindoline-2-carboxamide monohydrate

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

PMCID: PMC2961084 PMID: 21202279

Abstract

The title compound, C₁₀H₁₀N₂O₂·H₂O, is dimerized by inversion-related intermolecular N—H⋯O hydrogen bonding. There is an intramolecular N—H⋯O bond, resulting in a six-membered ring. Each dimer interacts with other dimers through hydrogen bonding with water molecules. The water molecules are linked to each other in a stair-like chain, thus generating two-dimensional polymeric strips. The dimers are also linked to each other through intermolecular C—H⋯O hydrogen bonding. There are π–π interactions between the aromatic and heterocyclic five-membered rings [centroid–centroid distance 3.8360 (12) Å]. C—H⋯π interactions also exist between CH₂ groups and aromatic rings.

Related literature

For related literature, see: Alberto et al. (1994 ▶); Berger et al. (1999 ▶); Cignarella et al. (1981 ▶); Maliha et al. (2008 ▶); Mancilla et al. (2007 ▶); Toru et al. (1986 ▶); Wan et al. (2007 ▶); Straub et al. (2007 ▶); Maliha et al. (2007 ▶).

Experimental

Crystal data

C₁₀H₁₀N₂O₂·H₂O
M _r = 208.22
Monoclinic,
a = 7.4264 (4) Å
b = 29.0200 (16) Å
c = 4.8864 (2) Å
β = 108.266 (3)°
V = 1000.02 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 (2) K
0.22 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.980, T _max = 0.990
18083 measured reflections
2518 independent reflections
1586 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.130
S = 1.05
2518 reflections
145 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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 (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008362/bq2071sup1.cif

e-64-0o786-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008362/bq2071Isup2.hkl

e-64-0o786-Isup2.hkl^{(121.2KB, 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—H2⋯O1	0.83 (3)	2.08 (2)	2.748 (3)	137 (2)
N2—H2⋯O1ⁱ	0.83 (2)	2.41 (2)	3.043 (2)	134 (2)
O3—H1W⋯O2ⁱⁱ	0.81 (3)	2.06 (3)	2.875 (2)	177 (3)
O3—H2W⋯O3ⁱⁱⁱ	0.88 (3)	1.91 (3)	2.787 (3)	174 (3)
C4—H4⋯O2^iv	0.93	2.44	3.362 (3)	172
C8—H8A⋯Cg1^v	0.97	2.86	3.590 (2)	133

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of atoms C2–C7.

Acknowledgments

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for providing the Kappa APEXII CCD diffractometer.

supplementary crystallographic information

Comment

Isoindole and their derivatives are known to be active-compounds pharmaceutically (Straub et al., 2007; Mancilla et al., 2007). They are important intermediates in the synthesis of novel multi-drugs resistance reversal agents (Berger et al., 1999). They show diuretic, anti-anginal, cardio-vascular and herbicidal activitities (Alberto et al., 1994; Cignarella et al., 1981; Toru et al., 1986).

The title compound (I) is in continuation to the synthesis of various isoindoles and the determination of their structures by X-ray crystallography (Maliha et al., 2007; 2008). It was isolated during the studies of the reaction of urea and its N-alkyl/aryl derivates with o-phthaldehyde.

The present structure shows that replacing the H-atom of 1-Oxoisoindoline-2- carboxamide (Maliha et al., 2008) with CH₃ group, is possible in the presence of crystallization water only. The replacement of H-atom of 1-Oxoisoindoline-2-carboxamide with ethyl group (Wan et al., 2007) also shows the existence of crystallizing H₂O. Although the bond distances and bond angles in the aromatic A(C2—C7) and five-membered ring B(C1/C2/C7/C8/N1) are comparable with the reported structures (Maliha et al., 2008; Wan et al., 2007), but the packing through H-bonding is entirely different. There is an intramolecular hydrogen bond of N2—H2···O1 resulting in a six-membered ring. The title compound is dimerized by inversion of N-methyl-1-oxo-1,3-dihydro-2H-isoindole-2-carboxamide through intermolecular H-bond viz N2—H2···O1ⁱ [symmetry code i = -x,-y,-z] and the central ring is of four members depending upon these H-bonds only. The role of H₂O molecules is to stabilize the dimers through an interesting H-bonding. The H-bond O3—H1W···O2ⁱⁱ [symmetry code ii = x + 1, y, z] connects the dimers, while the O3—H2W···O3ⁱⁱⁱ [symmetry code iii = x, -y + 1/2, z - 1/2] joints the water molecules in a stair like chain. In this way two-dimensional polymeric strip is realized. These polymeric strips are further connected by the involvement of aromatic ring A(C2—C7) through intermolecular H-bonds C4—H4···O2^iv [symmetry code iv = x + 1, y, z - 1]. The detail of H-bonding is given in Table 1 and shown in Fig. 2. The π-π interaction exist between the CgA···CgB^v [symmetry code v = x,y,z - 1] and CgB···CgA^vi [symmetry code vi = x,y,z + 1] having same centroid-centroid distance of 3.8360 (12) Å. The C—H···π interaction exists between C8—H8A and CgA^vi [symmetry code vi = x,y,z + 1] with H8A···π distance of 2.86 Å.

Experimental

A mixture of o-phthaldehyde (0.67 g, 200 mmol) and N-methylurea (0.37 g, 200 mmol) in 100 ml of ethanol was refluxed for 10 h. The solvent was taken off and flask contents were left at room temperature. The crystals of (I) were isolated, washed with ethanol, ether and n-hexane, respectively and dried. Crystals suitable for X-ray diffraction were grown from a mixture of methanol-acetone (1:1) by slow evaporation at room temperature. It is soluble in DMSO, DMF, acetone, ethyl acetate, chloroform and carbon tetrachloride. M.P: 413 K; yield: 60 percent.