2-(4-Bromo-phen-yl)-N-[3-(1H-imidazol-1-yl)prop-yl]quinazolin-4-amine.

In the title compound, C(20)H(18)BrN(5), the bromo-phenyl-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, mol-ecules 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 inter-actions possible between adjacent dimers [centroid-centroid distances = 3.7674 (16) and 3.7612 (17) Å]. There are also a number of C-H⋯π inter-actions 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 = 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

Δρmax = 0.94 e Å−3

Δρmin = −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 ▶).

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

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

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

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

C20H18BrN5	Z = 2
Mr = 408.30	F(000) = 416
Triclinic, P1	Dx = 1.485 Mg m−3
Hall symbol: -P 1	Melting point = 438–440 K
a = 8.8557 (7) Å	Cu Kα radiation, λ = 1.5418 Å
b = 9.5113 (6) Å	Cell parameters from 4656 reflections
c = 11.3730 (7) Å	θ = 4.0–72.6°
α = 99.682 (5)°	µ = 3.17 mm−1
β = 101.432 (6)°	T = 180 K
γ = 97.211 (6)°	Plate, colourless
V = 912.96 (11) Å3	0.4 × 0.2 × 0.07 mm

Agilent SuperNova, Dual, Cu, Atlas diffractometer	6845 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	6259 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.000
Detector resolution: 10.4679 pixels mm-1	θmax = 73.4°, θmin = 4.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.343, Tmax = 1.000	l = −14→14
6845 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.1707P)2 + 0.1234P] where P = (Fo2 + 2Fc2)/3
6845 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.87 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br26	1.29926 (4)	0.38228 (3)	0.53762 (3)	0.0344 (2)
N2	0.3265 (3)	0.9940 (3)	0.7534 (3)	0.0332 (8)
N5	0.5204 (3)	0.8708 (2)	0.7429 (2)	0.0226 (6)
N9	0.8641 (3)	0.8764 (3)	1.0859 (2)	0.0249 (7)
N17	1.2170 (3)	0.6321 (2)	1.1230 (2)	0.0219 (6)
N25	1.0223 (2)	0.7362 (2)	1.0039 (2)	0.0208 (6)
C1	0.3882 (3)	0.8826 (3)	0.7826 (3)	0.0271 (8)
C3	0.4247 (4)	1.0562 (3)	0.6895 (3)	0.0363 (10)
C4	0.5446 (4)	0.9818 (3)	0.6823 (3)	0.0320 (9)
C6	0.6173 (3)	0.7581 (3)	0.7585 (3)	0.0281 (8)
C7	0.6775 (3)	0.7528 (3)	0.8922 (3)	0.0244 (8)
C8	0.7867 (3)	0.8907 (3)	0.9637 (3)	0.0243 (8)
C10	0.9798 (3)	0.7984 (3)	1.1023 (2)	0.0211 (7)
C11	1.0576 (3)	0.7841 (3)	1.2228 (2)	0.0202 (7)
C12	1.0225 (3)	0.8494 (3)	1.3326 (3)	0.0272 (8)
C13	1.1050 (4)	0.8314 (3)	1.4436 (3)	0.0300 (8)
C14	1.2239 (3)	0.7465 (3)	1.4478 (3)	0.0276 (8)
C15	1.2587 (3)	0.6803 (3)	1.3418 (3)	0.0256 (8)
C16	1.1774 (3)	0.6981 (3)	1.2261 (3)	0.0210 (7)
C18	1.1381 (3)	0.6553 (3)	1.0193 (2)	0.0201 (7)
C19	1.1755 (3)	0.5861 (3)	0.9036 (2)	0.0198 (7)
C20	1.0851 (3)	0.5960 (3)	0.7895 (3)	0.0243 (7)
C21	1.1213 (3)	0.5346 (3)	0.6819 (3)	0.0259 (8)
C22	1.2489 (3)	0.4630 (3)	0.6873 (3)	0.0240 (8)
C23	1.3403 (3)	0.4505 (3)	0.7974 (3)	0.0258 (8)
C24	1.3025 (3)	0.5117 (3)	0.9049 (3)	0.0231 (7)
H1	0.34540	0.81910	0.82590	0.0320*
H3	0.41070	1.13760	0.65600	0.0440*
H4	0.62630	1.00180	0.64420	0.0380*
H6A	0.70550	0.77570	0.72110	0.0340*
H6B	0.55640	0.66490	0.71630	0.0340*
H7A	0.73260	0.67130	0.89680	0.0290*
H7B	0.58930	0.73740	0.93000	0.0290*
H8A	0.86520	0.91490	0.91860	0.0290*
H8B	0.72720	0.96950	0.97080	0.0290*
H9	0.83500	0.91890	1.14850	0.0300*
H12	0.94310	0.90500	1.33010	0.0330*
H13	1.08190	0.87550	1.51590	0.0360*
H14	1.27960	0.73500	1.52300	0.0330*
H15	1.33660	0.62310	1.34600	0.0310*
H20	1.00000	0.64450	0.78660	0.0290*
H21	1.06090	0.54110	0.60670	0.0310*
H23	1.42530	0.40190	0.79930	0.0310*
H24	1.36270	0.50330	0.97950	0.0280*

	U11	U22	U33	U12	U13	U23
Br26	0.0438 (3)	0.0463 (3)	0.0199 (2)	0.0198 (2)	0.0142 (2)	0.0076 (2)
N2	0.0312 (12)	0.0421 (14)	0.0294 (13)	0.0157 (11)	0.0077 (11)	0.0076 (12)
N5	0.0226 (10)	0.0276 (11)	0.0187 (11)	0.0058 (8)	0.0035 (9)	0.0079 (9)
N9	0.0255 (11)	0.0311 (12)	0.0193 (11)	0.0132 (9)	0.0041 (9)	0.0035 (9)
N17	0.0201 (10)	0.0284 (11)	0.0188 (11)	0.0081 (8)	0.0040 (8)	0.0066 (9)
N25	0.0192 (9)	0.0281 (11)	0.0164 (11)	0.0075 (8)	0.0041 (8)	0.0049 (9)
C1	0.0240 (12)	0.0355 (14)	0.0251 (14)	0.0070 (11)	0.0086 (11)	0.0102 (12)
C3	0.0420 (17)	0.0329 (15)	0.0386 (19)	0.0120 (12)	0.0108 (14)	0.0131 (14)
C4	0.0318 (14)	0.0332 (15)	0.0347 (17)	0.0042 (11)	0.0114 (12)	0.0131 (13)
C6	0.0297 (13)	0.0333 (14)	0.0211 (14)	0.0133 (11)	0.0043 (11)	0.0009 (11)
C7	0.0221 (12)	0.0281 (13)	0.0257 (14)	0.0093 (10)	0.0046 (10)	0.0101 (11)
C8	0.0269 (13)	0.0260 (13)	0.0219 (14)	0.0088 (10)	0.0031 (11)	0.0092 (11)
C10	0.0186 (11)	0.0244 (12)	0.0202 (13)	0.0044 (9)	0.0034 (10)	0.0049 (10)
C11	0.0190 (11)	0.0244 (12)	0.0168 (13)	0.0024 (9)	0.0039 (9)	0.0038 (10)
C12	0.0254 (12)	0.0342 (15)	0.0213 (14)	0.0093 (11)	0.0052 (11)	0.0008 (12)
C13	0.0322 (14)	0.0384 (15)	0.0175 (14)	0.0070 (12)	0.0060 (11)	−0.0014 (12)
C14	0.0289 (13)	0.0334 (14)	0.0180 (13)	0.0033 (11)	−0.0001 (11)	0.0055 (11)
C15	0.0231 (12)	0.0328 (14)	0.0224 (14)	0.0071 (10)	0.0031 (10)	0.0102 (12)
C16	0.0197 (11)	0.0243 (12)	0.0195 (13)	0.0024 (9)	0.0050 (10)	0.0063 (10)
C18	0.0187 (11)	0.0244 (12)	0.0185 (13)	0.0036 (9)	0.0053 (10)	0.0063 (10)
C19	0.0183 (11)	0.0250 (12)	0.0177 (13)	0.0045 (9)	0.0054 (9)	0.0066 (10)
C20	0.0199 (11)	0.0351 (14)	0.0190 (13)	0.0092 (10)	0.0023 (10)	0.0072 (11)
C21	0.0253 (12)	0.0358 (14)	0.0172 (13)	0.0085 (11)	0.0024 (10)	0.0072 (11)
C22	0.0283 (13)	0.0289 (13)	0.0163 (13)	0.0051 (10)	0.0097 (10)	0.0029 (11)
C23	0.0264 (12)	0.0311 (13)	0.0241 (14)	0.0127 (10)	0.0095 (11)	0.0068 (11)
C24	0.0217 (12)	0.0308 (13)	0.0197 (13)	0.0081 (10)	0.0041 (10)	0.0108 (11)

Br26—C22	1.906 (3)	C19—C24	1.401 (4)
N2—C1	1.313 (4)	C19—C20	1.408 (4)
N2—C3	1.379 (4)	C20—C21	1.380 (4)
N5—C1	1.346 (4)	C21—C22	1.387 (4)
N5—C4	1.372 (4)	C22—C23	1.382 (4)
N5—C6	1.467 (4)	C23—C24	1.385 (4)
N9—C8	1.459 (4)	C1—H1	0.9300
N9—C10	1.340 (4)	C3—H3	0.9300
N17—C16	1.365 (4)	C4—H4	0.9300
N17—C18	1.314 (3)	C6—H6A	0.9700
N25—C10	1.321 (3)	C6—H6B	0.9700
N25—C18	1.359 (3)	C7—H7A	0.9700
N9—H9	0.8600	C7—H7B	0.9700
C3—C4	1.356 (5)	C8—H8A	0.9700
C6—C7	1.520 (5)	C8—H8B	0.9700
C7—C8	1.526 (4)	C12—H12	0.9300
C10—C11	1.443 (3)	C13—H13	0.9300
C11—C16	1.417 (4)	C14—H14	0.9300
C11—C12	1.408 (4)	C15—H15	0.9300
C12—C13	1.377 (5)	C20—H20	0.9300
C13—C14	1.403 (4)	C21—H21	0.9300
C14—C15	1.373 (4)	C23—H23	0.9300
C15—C16	1.417 (5)	C24—H24	0.9300
C18—C19	1.487 (3)
C1—N2—C3	104.7 (3)	C22—C23—C24	118.6 (3)
C1—N5—C4	106.9 (2)	C19—C24—C23	121.4 (3)
C1—N5—C6	126.4 (2)	N2—C1—H1	124.00
C4—N5—C6	126.7 (3)	N5—C1—H1	124.00
C8—N9—C10	121.2 (2)	N2—C3—H3	125.00
C16—N17—C18	115.5 (2)	C4—C3—H3	125.00
C10—N25—C18	118.1 (2)	N5—C4—H4	127.00
C8—N9—H9	119.00	C3—C4—H4	127.00
C10—N9—H9	119.00	N5—C6—H6A	109.00
N2—C1—N5	112.3 (3)	N5—C6—H6B	109.00
N2—C3—C4	110.4 (3)	C7—C6—H6A	109.00
N5—C4—C3	105.7 (3)	C7—C6—H6B	109.00
N5—C6—C7	112.6 (2)	H6A—C6—H6B	108.00
C6—C7—C8	112.8 (2)	C6—C7—H7A	109.00
N9—C8—C7	112.5 (2)	C6—C7—H7B	109.00
N9—C10—N25	117.6 (2)	C8—C7—H7A	109.00
N9—C10—C11	121.7 (2)	C8—C7—H7B	109.00
N25—C10—C11	120.8 (2)	H7A—C7—H7B	108.00
C10—C11—C12	124.6 (3)	N9—C8—H8A	109.00
C12—C11—C16	120.0 (2)	N9—C8—H8B	109.00
C10—C11—C16	115.4 (2)	C7—C8—H8A	109.00
C11—C12—C13	120.4 (3)	C7—C8—H8B	109.00
C12—C13—C14	120.0 (3)	H8A—C8—H8B	108.00
C13—C14—C15	120.6 (3)	C11—C12—H12	120.00
C14—C15—C16	120.8 (3)	C13—C12—H12	120.00
N17—C16—C11	122.8 (3)	C12—C13—H13	120.00
C11—C16—C15	118.2 (3)	C14—C13—H13	120.00
N17—C16—C15	119.0 (3)	C13—C14—H14	120.00
N17—C18—C19	118.2 (2)	C15—C14—H14	120.00
N25—C18—C19	114.5 (2)	C14—C15—H15	120.00
N17—C18—N25	127.4 (2)	C16—C15—H15	120.00
C20—C19—C24	118.3 (2)	C19—C20—H20	120.00
C18—C19—C20	120.6 (2)	C21—C20—H20	120.00
C18—C19—C24	121.2 (2)	C20—C21—H21	120.00
C19—C20—C21	120.8 (3)	C22—C21—H21	120.00
C20—C21—C22	119.1 (3)	C22—C23—H23	121.00
Br26—C22—C23	119.7 (2)	C24—C23—H23	121.00
Br26—C22—C21	118.4 (2)	C19—C24—H24	119.00
C21—C22—C23	121.9 (3)	C23—C24—H24	119.00
C3—N2—C1—N5	0.8 (4)	C10—C11—C12—C13	−178.9 (3)
C1—N2—C3—C4	−0.5 (4)	C16—C11—C12—C13	0.6 (4)
C4—N5—C1—N2	−0.8 (4)	C10—C11—C16—N17	−0.4 (4)
C6—N5—C1—N2	−179.2 (3)	C10—C11—C16—C15	179.8 (3)
C1—N5—C4—C3	0.4 (3)	C12—C11—C16—N17	−180.0 (3)
C6—N5—C4—C3	178.8 (3)	C12—C11—C16—C15	0.2 (4)
C1—N5—C6—C7	−58.8 (4)	C11—C12—C13—C14	−0.6 (5)
C4—N5—C6—C7	123.2 (3)	C12—C13—C14—C15	−0.3 (5)
C10—N9—C8—C7	73.6 (3)	C13—C14—C15—C16	1.1 (4)
C8—N9—C10—N25	0.7 (4)	C14—C15—C16—N17	179.1 (3)
C8—N9—C10—C11	179.7 (3)	C14—C15—C16—C11	−1.0 (4)
C18—N17—C16—C11	1.1 (4)	N17—C18—C19—C20	174.0 (3)
C18—N17—C16—C15	−179.0 (3)	N17—C18—C19—C24	−7.1 (4)
C16—N17—C18—N25	−0.4 (4)	N25—C18—C19—C20	−5.5 (4)
C16—N17—C18—C19	−179.9 (2)	N25—C18—C19—C24	173.4 (3)
C18—N25—C10—N9	−179.2 (3)	C18—C19—C20—C21	178.6 (3)
C18—N25—C10—C11	1.8 (4)	C24—C19—C20—C21	−0.3 (4)
C10—N25—C18—N17	−1.1 (4)	C18—C19—C24—C23	−178.2 (3)
C10—N25—C18—C19	178.4 (2)	C20—C19—C24—C23	0.7 (4)
N2—C3—C4—N5	0.1 (4)	C19—C20—C21—C22	−0.3 (4)
N5—C6—C7—C8	−63.8 (3)	C20—C21—C22—Br26	−178.8 (2)
C6—C7—C8—N9	−170.6 (2)	C20—C21—C22—C23	0.5 (4)
N9—C10—C11—C12	−0.6 (5)	Br26—C22—C23—C24	179.2 (2)
N9—C10—C11—C16	179.9 (3)	C21—C22—C23—C24	−0.1 (4)
N25—C10—C11—C12	178.4 (3)	C22—C23—C24—C19	−0.5 (4)
N25—C10—C11—C16	−1.2 (4)

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···Cg1iv	0.93	2.88	3.527 (3)	128

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⋯Cg1iv	0.93	2.88	3.527 (3)	128

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