3-(4-Chloro­phen­yl)-2-(diisopropyl­amino)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one

Quan-Bin Liao; Gui-Hua Li; Zheng-Rong Zhu; Ming-Guo Liu

doi:10.1107/S1600536807060412

. 2007 Dec 6;64(Pt 1):o13. doi: 10.1107/S1600536807060412

3-(4-Chlorophenyl)-2-(diisopropylamino)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one

Quan-Bin Liao ^a, Gui-Hua Li ^b,^*, Zheng-Rong Zhu ^c, Ming-Guo Liu ^a

PMCID: PMC2914975 PMID: 21200694

Abstract

In the molecule of the title compound, C₂₂H₂₂ClN₃O₂, the three fused rings of the benzofuro[3,2-d]pyrimidine system are almost coplanar. This ring system is oriented with respect to the substituted benzene ring at a dihedral angle of 79.05 (3)°. Intramolecular C—H⋯N hydrogen bonding results in the formation of a six-membered ring. In the crystal structure, π–π stacking interactions involving the furan, pyrimidinone and benzene rings are present [centroid-to-centroid distances in the range 3.258 (1)–3.870 (1) Å].

Related literature

For general background, see: Bodke & Sangapure (2003 ▶); Ding et al. (2004 ▶); Janiak (2000 ▶). For a related structure, see: Liu et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₂H₂₂ClN₃O₂
M _r = 395.88
Monoclinic,
a = 11.3713 (7) Å
b = 23.2686 (10) Å
c = 7.8405 (5) Å
β = 105.994 (1)°
V = 1994.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.958, T _max = 0.979
6825 measured reflections
3919 independent reflections
3221 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.139
S = 1.14
3919 reflections
257 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1735 Friedel pairs
Flack parameter: −0.01 (9)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Bruker, 2001 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060412/hk2383sup1.cif

e-64-00o13-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060412/hk2383Isup2.hkl

e-64-00o13-Isup2.hkl^{(192.1KB, 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
C15—H15A⋯N2	0.96	2.44	2.946 (5)	113

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Acknowledgments

The authors gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (grant No. 20102001).

supplementary crystallographic information

Comment

The derivatives of benzofuropyrimidines are of great importance because of their remarkable biological properties (Bodke & Sangapure, 2003). In recent years, we have been engaged in the preparation of derivatives of heterocycles using an aza-Wittig reaction (Ding et al., 2004). The heterocyclic title compound, (I), may be used as a new precursor for obtaining bioactive molecules, and we report herein its crystal structure.

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987). They are also in agreement with the corresponding values in a reported similar compound (Liu et al., 2006). The three fused rings, A (N1/N2/C7–C10), B (O2/C8/C9/C17/C22) and C (C17–C22), of the benzofuro[3,2-d]pyrimidine system are almost co-planar, with a maximum deviation of 0.029 (3) Å (for C17). The co-planar ring system is oriented with respect to the substituted benzene ring D (C1–C6) at a dihedral angle of 79.05 (3)°. The intramolecular C—H···O hydrogen bond (Table 1) results in the formation of a six-membered ring.

Intermolecular π–π stacking interactions (Janiak, 2000) involving the furan, pyrimidinone and benzene rings seem to be effective in stabilizing the crystal structure (Fig. 2). The furan:furan and furan:pyrimidinone interplanar distances are 3.728 (1) Å and 3.510 (1) Å, while the distances between the adjacent ring centroids are 3.870 (1) Å and 3.744 (1) Å [symmetry code: x, 1 - y, -1/2 + z], respectively. A further interaction occurs between the two adjacent furan and benzene rings [symmetry code: x, 1 - y, 1/2 + z] with an interplanar distance of 3.258 (1) Å and a centroid-to-centroid distance of 3.870 (1) Å.

Experimental

For the preparation of the title compound, diisopropylamine (3 mmol) was added to a solution of ethyl 3-((4-chlorophenylimino)methyleneamino)-benzofuran-2-carboxylate (3 mmol) in dichloromethane (5 ml). After stirring the reaction mixture for 1 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 2 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from ethanol to give the title compound (yield; 82%). Single crystals suitable for X-ray analysis were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.