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

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.

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 (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 Et 3 N (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).

Refinement
The crystal is a non-merohedral twin, with a minor twin fraction of 0.47. Two components rotated by 180 ° around an axis close to the a axis were used to produce an HKLF5 file that was used in the refinement. The H atoms were included in calculated positions and treated as riding atoms: N-H = 0.86 Å, C-H = 0.93 and 0.97 Å for CH and CH 2 H atoms, respectively, with U iso (H) = 1.2U eq (parent N or C atom).    A view along the c axis of the crystal packing of the title compound. Hydrogen bonds are shown as blue dashed lines (see Table 1 for details).

Crystal data
C 20 H 18 BrN 5 M r = 408.30 Triclinic, P1 Hall symbol: -P 1 a = 8.8557 (7) Å b = 9.5113 (6) Å c = 11.3730 (7) Å α = 99.682 (5) where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.94 e Å −3 Δρ min = −0.87 e Å −3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles Refinement. The crystal is twinned. Two components rotated by 180 degrees around an axis close to the a axis were used to produce an hklf5 file that was used in the refinement. The twin fraction is 0.47.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq