2-(2-{[4-Oxo-3-(2-phenyl­eth­yl)-3,4-dihydro­quinazolin-2-yl]sulfan­yl}eth­yl)-2,3-dihydro-1H-isoindole-1,3-dione

Adel S El-Azab; Alaa A-M Abdel-Aziz; Abdulrahman M Al-Obaid; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812025883

. 2012 Jun 13;68(Pt 7):o2057–o2058. doi: 10.1107/S1600536812025883

2-(2-{[4-Oxo-3-(2-phenylethyl)-3,4-dihydroquinazolin-2-yl]sulfanyl}ethyl)-2,3-dihydro-1H-isoindole-1,3-dione

Adel S El-Azab ^a,^b,^‡, Alaa A-M Abdel-Aziz ^a,^c, Abdulrahman M Al-Obaid ^a, Seik Weng Ng ^d,^e, Edward R T Tiekink ^d,^*

PMCID: PMC3393323 PMID: 22807880

Abstract

In the title compound, C₂₆H₂₁N₃O₃S, the quinazolinyl group is essentially planar [r.m.s. deviation for the 10 non-H atoms = 0.057 Å]. The isoindoline-1,3-dione group is linked by an SCH₂CH₂ chain to the pyrimidinyl C atom that lies between the two N atoms. Also, the phenyl group is linked by a CH₂CH₂ chain at the N atom adjacent to the carbonyl group. This results in a conformation with these substituents lying to either side of the central quinazolinyl unit, with the former being approximately parallel [dihedral angle = 4.93 (7)°], and the phenyl group being inclined [dihedral angle = 71.61 (9)°] to the central quinazolinyl fused-ring system. In the crystal, molecules are consolidated into a three-dimensional architecture by C—H⋯O interactions, involving all three carbonyl-O atoms, and π–π interactions occurring between the pyrimidinyl and isoindole-benzene rings [inter-centroid distance = 3.5330 (13) Å].

Related literature

For the synthesis and drug discovery trials of quinazoline-4(3H)-one derivatives, see: El-Azab & ElTahir (2012 ▶); El-Azab et al. (2011 ▶). For the synthesis and antimicrobial activity of the title compound, see: El-Azab (2007 ▶). For a related structure, see: El-Emam et al. (2012 ▶).

Experimental

Crystal data

C₂₆H₂₁N₃O₃S
M _r = 455.52
Triclinic,
a = 8.7346 (4) Å
b = 9.4464 (6) Å
c = 13.7373 (8) Å
α = 94.258 (5)°
β = 103.505 (5)°
γ = 105.227 (5)°
V = 1052.27 (10) Å³
Z = 2
Cu Kα radiation
μ = 1.66 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.511, T _max = 1.000
7763 measured reflections
4329 independent reflections
3482 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.139
S = 1.03
4329 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536812025883/sj5240sup1.cif

e-68-o2057-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025883/sj5240Isup2.hkl

e-68-o2057-Isup2.hkl^{(212.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025883/sj5240Isup3.cml

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
C13—H13⋯O1ⁱ	0.95	2.56	3.218 (3)	127
C17—H17B⋯O3ⁱⁱ	0.99	2.42	3.120 (2)	128
C21—H21⋯O2ⁱⁱⁱ	0.95	2.45	3.346 (3)	157

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

Acknowledgments

We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

The title compound, 2-(2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)ethyl)isoindoline-1,3-dione (I), was originally synthesized for evaluation of its anti-microbial activity (El-Azab, 2007) owing to the known biological activity of related quinazoline-4(3H)one derivatives (El-Azab & ElTahir, 2012; El-Azab et al., 2011). Herein, we describe the crystal structure determination of (I).

In (I), Fig. 1, the quinazolinyl group is planar with the r.m.s. deviation for the 10 non-hydrogen atoms = 0.057 Å and maximum deviations of 0.062 (2) for the C5 atom and -0.068 (2) for the C7 atom. The isoindole (r.m.s. deviation for the nine non-hydrogen atoms = 0.018 Å), being linked by a SCH₂CH₂ chain at the C16 atom, and phenyl, linked by a CH₂CH₂ chain at the N2 atom, groups lie to either side of the molecule with the former being approximately parallel, dihedral angle = 4.93 (7)°, and the phenyl group being inclined, dihedral angle = 71.61 (9)°, with respect to the central quinazolinyl group.

Molecules are consolidated into a three-dimensional architecture by C—H···O interactions involving all three carbonyl-O atoms, Table 1, and π—π interactions occurring between the pyrimidinyl and isoindole-benzene rings [intercentroid distance = 3.5330 (13) Å, angle of inclination = 6.19 (10)° for symmetry operation: 1 - x, 2 - y, 1 - z], Fig. 2.

Experimental

A mixture of 2-mercapto-3-phenethylquinazolin-4(3H)-one (564 mg, 2 mmol) and 2-(2-chloroethyl)isoindoline-1,3-dione (418 mg, 2.0 mmol) in acetone (10 ml) containing anhydrous K₂CO₃ (300 mg) was stirred at room temperature for 12 h. The reaction mixture was filtered, the solvent removed under reduced pressure and the solid obtained was dried and recrystallized from ethanol. Yield 89%; ¹H NMR (CDCl₃): δ = 8.10 (d, 1H, J = 7.5 Hz), 7.72 (dd, 2H, J = 3.0 Hz), 7.62–7.56 (m, 4H), 7.29 (t, 1H, J = 6.5, 7.0 Hz), 7.21–7.15 (m, 5H), 4.17 (t, 2H, J = 8.0, 8.5 Hz), 4.10 (t, 2H, J = 6.0, 6.5 Hz), 3.54 (t, 2H, J = 6.5 Hz), 2.94 (t, 2H, J = 8.0, 8.5 Hz) p.p.m.. MS (70 eV): m/z = 455.