2-(4-Bromo­phen­yl)-N-[3-(1H-imidazol-1-yl)prop­yl]quinazolin-4-amine

Marcia Pérez-Fehrmann; Victor Kesternich; Felipe Verdugo; Philippe Christen; Céline Besnard

doi:10.1107/S1600536812028115

. 2012 Jun 30;68(Pt 7):o2249. doi: 10.1107/S1600536812028115

2-(4-Bromophenyl)-N-[3-(1H-imidazol-1-yl)propyl]quinazolin-4-amine

Marcia Pérez-Fehrmann ^a, Victor Kesternich ^a,^*, Felipe Verdugo ^a, Philippe Christen ^b, Céline Besnard ^c

PMCID: PMC3394037 PMID: 22798902

Abstract

In the title compound, C₂₀H₁₈BrN₅, the bromophenyl-substituted quinazoline unit is essentially planar [maximum deviation = 0.098 (3) Å] and makes a dihedral angle of 56.04 (14)° with the imidazole ring. In the crystal, molecules are associated by pairs of N—H⋯N hydrogen bonds to form inversion dimers. All the quinazoline planar systems are oriented almost perpendicular to the [110] direction, making π–π interactions possible between adjacent dimers [centroid–centroid distances = 3.7674 (16) and 3.7612 (17) Å]. There are also a number of C—H⋯π interactions present. The crystal is a nonmerohedral twin, with a minor twin fraction of 0.47.

Related literature

For general background on the biological properties of imidazo quinazolines, see: Aguilar et al. (2002 ▶); Rohini et al. (2009 ▶). For imidazo quinazoline structures, see: Asproni et al. (2011 ▶); Connolly et al. (2005 ▶). For synthetic details, see: Okano et al. (2009 ▶).

Experimental

Crystal data

C₂₀H₁₈BrN₅
M _r = 408.30
Triclinic,
a = 8.8557 (7) Å
b = 9.5113 (6) Å
c = 11.3730 (7) Å
α = 99.682 (5)°
β = 101.432 (6)°
γ = 97.211 (6)°
V = 912.96 (11) Å³
Z = 2
Cu Kα radiation
μ = 3.17 mm⁻¹
T = 180 K
0.4 × 0.2 × 0.07 mm

Data collection

Agilent SuperNova, Dual, Cu, Atlas diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.343, T _max = 1.000
6845 measured reflections
6845 independent reflections
6259 reflections with I > 2σ(I)

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.216
S = 1.12
6845 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −0.87 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028115/su2454sup1.cif

e-68-o2249-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028115/su2454Isup2.hkl

e-68-o2249-Isup2.hkl^{(334.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812028115/su2454Isup3.cml

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

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

Cg1 is the centroid of the N2,N5,C1–C3 ring; Cg3 is the centroid of the C11–C16 ring; Cg4 is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯N2ⁱ	0.86	2.14	2.949 (4)	156
C1—H1⋯Cg4ⁱⁱ	0.93	2.84	3.605 (3)	140
C4—H4⋯Cg3ⁱⁱⁱ	0.93	2.78	3.509 (4)	136
C14—H14⋯Cg1^iv	0.93	2.88	3.527 (3)	128

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

supplementary crystallographic information

Comment

Imidazo quinazolines (Connolly et al., 2005; Asproni et al., 2011) are heterocyclic compounds that exhibit a wide range of biological activities such as, antibacterial, antifungal, and antitumor (Rohini et al., 2009). The importance of this type of structure is linked to the fact that new drugs are permanently required owing to the fact that microorganisms are mutating continuously (Aguilar et al., 2002).

In the title compound, Fig. 1, the bromophenyl substituted quinazoline unit is essentially planar, with a maximum deviation 0.098 (3)Å for atom C20, and makes a dihedral angle of 56.04 (14) ° with the imidazole ring.

In the crystal, the molecules are associated via N-H···N hydrogen bonds, involving the imidazole function (N2) and the NH group to form inversion dimers (Table 1 and Fig. 2). All the planar quinazoline systems are oriented almost perpendicular to direction [110] making π···π interactions possible between adjacent dimers [Fig 3; Cg2···Cg4ⁱ 3.7674 (16) Å; Cg3···Cg4ⁱ 3.7612 (17) Å; symmetry code (i) -x+2, -y+1, -z+2; Cg2, Cg3 and Cg4 are the centroids of rings (N25,C10,C11,C16,N17,C18), (C11-C16) and (C19-C20), respectively]. There are also a number of C-H···π interactions present (Table 1).

Experimental

Both the starting reagent, 4-chloro-2-(4-bromophenyl)quinazoline, and the title compound were synthesized as described by (Okano et al., 2009). To a stirred solution of 0.4 g of 4-chloro-2-(4-bromophenyl)quinazoline (1,3 mmol) in 6 ml of N,N-dimethylformamide, a mixture of 0.4 ml of Et₃N (2.6 mmol) and 0.2 ml of 1-(3-aminopropyl)-imidazole (1.6 mmol) were added. The reaction mixture was stirred at room temperature for 4 h. After completion of the reaction 30 ml of cold water were added giving a white precipitate of the title compound that was purified in acetone [Yield 95%]. Recrystallization in acetone at room temperature afforded colourless plate-like crystals suitable for X-ray diffraction analysis (M.p. 438-440 K).