Ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)benzoate

Yi Chen Chan; Abdussalam Salhin; Melati Khairuddean; Madhukar Hemamalini; Hoong-Kun Fun

doi:10.1107/S160053681005049X

. 2010 Dec 11;67(Pt 1):o98–o99. doi: 10.1107/S160053681005049X

Ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)benzoate

Yi Chen Chan ^a, Abdussalam Salhin ^a,^‡, Melati Khairuddean ^a, Madhukar Hemamalini ^b, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC3050286 PMID: 21522807

Abstract

The title compound, C₂₁H₁₅NO₄, was synthesized by reducing the Schiff base obtained from acenaphthenequinone and ethyl-4-aminobenzoate. The dihedral angle between the essentially planar 1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline ring system [maximum deviation = 0.061 (2) Å] and the benzene ring is 75.08 (10)°. In the crystal, molecules are connected via weak intermolecular C—H⋯O hydrogen bonds, forming a two-dimensional network. The ethyl group is disordered over two sets of sites with a refined occupancy ratio of 0.502 (12):0.498 (12).

Related literature

For details and applications of acenaphthenquinone-based Schiff bases, see: Maldanis et al. (2002 ▶); Son et al. (2006 ▶); Mhaidat et al. (2009 ▶); Rodriguez-Argüelles et al. (1997 ▶); McDavid et al. (1951 ▶); Salhin et al. (2007 ▶, 2008 ▶, 2009 ▶); Tameem et al. (2006 ▶, 2007 ▶, 2008 ▶); Shalash et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₁H₁₅NO₄
M _r = 345.34
Monoclinic,
a = 5.2025 (7) Å
b = 18.066 (3) Å
c = 17.560 (2) Å
β = 98.365 (2)°
V = 1632.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.49 × 0.21 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.953, T _max = 0.992
15726 measured reflections
2393 independent reflections
2157 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.171
S = 1.07
2393 reflections
256 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005049X/lh5180sup1.cif

e-67-00o98-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005049X/lh5180Isup2.hkl

e-67-00o98-Isup2.hkl^{(115.2KB, 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
C7—H7A⋯O3ⁱ	0.93	2.60	3.249 (4)	127
C14—H14A⋯O1ⁱⁱ	0.93	2.41	3.312 (3)	165

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

YCC, AS and MK acknowledge financial support by the Universiti Sains Malaysia (USM) under the Science Fund Grant No. 1001/PKIMIA/823003. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Acenaphthenequinone-based Schiff bases have been widely synthesized due to their significant applications in chemistry (Maldanis et al., 2002; Son et al., 2006), physics (Mhaidat et al., 2009) and pharmacology (Rodriguez-Argüelles et al., 1997; McDavid et al., 1951). As a continuation of the interest of our research group on the synthesis of Schiff base derivatives (Salhin et al., 2007, 2008, 2009; Tameem et al., 2006, 2007, 2008; Shalash et al., 2010), the title compound was prepared through the reduction of the Schiff base which was obtained from the condensation reaction of acenaphthenequinone and ethyl-4-aminobenzoate.

The molecular structure of the title compound is shown in Fig. 1. The 1,3-dioxo-1H-benzo[de]isoquinoline (O1–O2/N1/C1–C12) ring is approximately planar with maximum deviation of 0.061 (2) Å for atom N1. The ethyl group is disordered over two sites with a refined occupancy ratio of 0.502 (12):0.498 (12). The dihedral angle between the 1,3-dioxo-1H-benzo[de]isoquinoline (O1–O2/N1/C1–C12) ring and the benzene (C13–C18) ring is 75.08 (10)°.

In the crystal structure (Fig. 2), adjacent molecules are connected via intermolecular C7—H7A···O3ⁱ and C14—H14A···O1ⁱⁱ (Table 1) hydrogen bonds to form a two-dimensional network.

Experimental

A mixture of acenaphthenequinone (0.182 g, 1 mmol), ethyl-4-aminobenzoate (0.165 g, 1 mmol) and methanol (30 mL) was allowed to reflux for overnight. The synthesized Schiff base was then reduced using NaBH₄ in ethanol with stirring at room temperature. Crystal of (I) suitable for X-ray crystallography was obtained by recrystallization from ethanol.