2-(4-Bromo-phen-yl)-2-methyl-2,3-di-hydro-quinazolin-4(1H)-one.

In the title compound, C(15)H(13)BrN(2)O, the pyrimidine ring adopts a skew boat conformation. The amino H atom forms an inter-molecular hydrogen bond with the carbonyl O atom of an adjacent mol-ecule, forming an inversion dimer. Another lone pair of electrons on the same carbonyl O atom acts as acceptor for another N-H⋯O inter-molecular hydrogen bond with a neighbouring mol-ecule, forming chains along the c axis.

Related literature

For biological properties of quinazolinone derivatives, see: Alagarsamy et al. (2006 ▶, 2007 ▶); Hwang et al. (2008 ▶); Na et al. (2008 ▶); Nandy et al. (2006 ▶). For related structures, see: Wang et al. (2008 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C15H13BrN2O

M = 317.18

Monoclinic,

a = 12.2106 (3) Å

b = 9.0507 (2) Å

c = 12.4046 (3) Å

β = 101.719 (1)°

V = 1342.31 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.06 mm−1

T = 296 K

0.39 × 0.31 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.343, T max = 0.801

16905 measured reflections

2369 independent reflections

2068 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.087

S = 1.05

2369 reflections

181 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.89 e Å−3

Δρmin = −0.86 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012584/pv2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012584/pv2270Isup2.hkl

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

C15H13BrN2O	F(000) = 640
Mr = 317.18	Dx = 1.570 Mg m−3
Monoclinic, P21/c	Melting point = 494–496 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.2106 (3) Å	Cell parameters from 7144 reflections
b = 9.0507 (2) Å	θ = 2.8–27.1°
c = 12.4046 (3) Å	µ = 3.06 mm−1
β = 101.719 (1)°	T = 296 K
V = 1342.31 (5) Å3	Block, colourless
Z = 4	0.39 × 0.31 × 0.07 mm

Bruker SMART CCD area-detector diffractometer	2369 independent reflections
Radiation source: fine-focus sealed tube	2068 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −14→14
Tmin = 0.343, Tmax = 0.801	k = −10→10
16905 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0402P)2 + 1.4299P] where P = (Fo2 + 2Fc2)/3
2369 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.89 e Å−3
2 restraints	Δρmin = −0.86 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.39200 (3)	0.15530 (4)	0.53610 (3)	0.06231 (16)
O1	0.12331 (16)	0.5903 (2)	−0.02983 (14)	0.0438 (5)
N2	0.14117 (19)	0.7611 (2)	0.27005 (18)	0.0356 (5)
C2	0.1400 (2)	0.6296 (3)	0.0687 (2)	0.0331 (6)
C10	0.1575 (2)	0.4972 (3)	0.3192 (2)	0.0305 (5)
N1	0.07053 (18)	0.5872 (3)	0.13329 (17)	0.0341 (5)
C15	0.1462 (2)	0.4648 (3)	0.4258 (2)	0.0423 (6)
H15A	0.0918	0.5136	0.4550	0.051*
C8	0.2278 (2)	0.7955 (3)	0.2193 (2)	0.0339 (6)
C7	0.3078 (2)	0.9022 (3)	0.2615 (2)	0.0430 (7)
H7A	0.3047	0.9501	0.3271	0.052*
C11	0.2387 (2)	0.4209 (3)	0.2788 (2)	0.0371 (6)
H11A	0.2471	0.4391	0.2071	0.045*
C3	0.2318 (2)	0.7284 (3)	0.1177 (2)	0.0342 (6)
C9	−0.0294 (2)	0.6307 (3)	0.2795 (2)	0.0418 (6)
H9A	−0.0752	0.6953	0.2278	0.050*
H9B	−0.0224	0.6699	0.3525	0.050*
H9C	−0.0633	0.5346	0.2760	0.050*
C1	0.0863 (2)	0.6182 (3)	0.2514 (2)	0.0312 (5)
C13	0.2944 (2)	0.2903 (3)	0.4473 (2)	0.0396 (6)
C14	0.2138 (3)	0.3620 (3)	0.4894 (2)	0.0462 (7)
H14A	0.2046	0.3415	0.5605	0.055*
C4	0.3171 (2)	0.7652 (3)	0.0637 (2)	0.0417 (6)
H4A	0.3202	0.7199	−0.0030	0.050*
C5	0.3972 (2)	0.8676 (4)	0.1070 (3)	0.0494 (7)
H5A	0.4546	0.8906	0.0707	0.059*
C12	0.3077 (2)	0.3185 (3)	0.3416 (2)	0.0416 (6)
H12A	0.3623	0.2693	0.3129	0.050*
C6	0.3913 (3)	0.9364 (3)	0.2060 (3)	0.0500 (7)
H6A	0.4447	1.0067	0.2352	0.060*
H2	0.146 (2)	0.794 (3)	0.3350 (12)	0.042 (8)*
H1	0.0147 (16)	0.535 (3)	0.103 (2)	0.035 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.0575 (2)	0.0674 (3)	0.0598 (2)	0.01474 (16)	0.00690 (16)	0.02754 (17)
O1	0.0550 (12)	0.0520 (12)	0.0237 (10)	−0.0116 (9)	0.0066 (8)	−0.0021 (8)
N2	0.0477 (13)	0.0326 (11)	0.0280 (12)	−0.0021 (10)	0.0111 (10)	−0.0048 (9)
C2	0.0381 (14)	0.0331 (13)	0.0269 (13)	0.0041 (11)	0.0038 (10)	0.0031 (10)
C10	0.0313 (12)	0.0325 (13)	0.0277 (13)	−0.0051 (10)	0.0064 (10)	−0.0031 (10)
N1	0.0361 (12)	0.0392 (12)	0.0257 (11)	−0.0056 (10)	0.0030 (9)	−0.0014 (9)
C15	0.0455 (16)	0.0506 (17)	0.0340 (15)	0.0063 (13)	0.0156 (12)	0.0007 (13)
C8	0.0374 (14)	0.0318 (13)	0.0311 (14)	0.0028 (11)	0.0036 (11)	0.0024 (11)
C7	0.0515 (17)	0.0393 (15)	0.0359 (15)	−0.0041 (13)	0.0030 (12)	−0.0031 (12)
C11	0.0417 (14)	0.0418 (15)	0.0301 (14)	0.0035 (12)	0.0129 (11)	0.0039 (11)
C3	0.0374 (14)	0.0353 (13)	0.0294 (13)	0.0018 (11)	0.0057 (11)	0.0016 (11)
C9	0.0376 (14)	0.0474 (16)	0.0416 (16)	0.0047 (12)	0.0111 (12)	0.0009 (13)
C1	0.0346 (13)	0.0338 (13)	0.0257 (13)	−0.0010 (10)	0.0075 (10)	−0.0022 (10)
C13	0.0366 (14)	0.0401 (15)	0.0394 (15)	−0.0012 (12)	0.0013 (11)	0.0088 (12)
C14	0.0519 (17)	0.0572 (18)	0.0307 (15)	0.0038 (14)	0.0116 (13)	0.0083 (13)
C4	0.0403 (15)	0.0485 (16)	0.0370 (15)	0.0016 (13)	0.0100 (12)	0.0010 (12)
C5	0.0365 (15)	0.0568 (19)	0.056 (2)	−0.0031 (13)	0.0116 (13)	0.0052 (15)
C12	0.0381 (15)	0.0444 (15)	0.0438 (16)	0.0054 (12)	0.0120 (12)	0.0021 (13)
C6	0.0428 (16)	0.0477 (17)	0.0556 (19)	−0.0108 (13)	0.0011 (14)	0.0004 (14)

Br1—C13	1.896 (3)	C7—H7A	0.9300
O1—C2	1.249 (3)	C11—C12	1.382 (4)
N2—C8	1.372 (3)	C11—H11A	0.9300
N2—C1	1.453 (3)	C3—C4	1.389 (4)
N2—H2	0.851 (10)	C9—C1	1.526 (4)
C2—N1	1.336 (3)	C9—H9A	0.9600
C2—C3	1.466 (4)	C9—H9B	0.9600
C10—C11	1.384 (4)	C9—H9C	0.9600
C10—C15	1.388 (4)	C13—C14	1.368 (4)
C10—C1	1.538 (3)	C13—C12	1.378 (4)
N1—C1	1.466 (3)	C14—H14A	0.9300
N1—H1	0.854 (10)	C4—C5	1.375 (4)
C15—C14	1.381 (4)	C4—H4A	0.9300
C15—H15A	0.9300	C5—C6	1.391 (4)
C8—C7	1.397 (4)	C5—H5A	0.9300
C8—C3	1.409 (4)	C12—H12A	0.9300
C7—C6	1.376 (4)	C6—H6A	0.9300
C8—N2—C1	120.2 (2)	H9A—C9—H9B	109.5
C8—N2—H2	116 (2)	C1—C9—H9C	109.5
C1—N2—H2	114 (2)	H9A—C9—H9C	109.5
O1—C2—N1	120.5 (2)	H9B—C9—H9C	109.5
O1—C2—C3	122.6 (2)	N2—C1—N1	107.0 (2)
N1—C2—C3	116.8 (2)	N2—C1—C9	108.4 (2)
C11—C10—C15	117.2 (2)	N1—C1—C9	107.6 (2)
C11—C10—C1	121.6 (2)	N2—C1—C10	110.9 (2)
C15—C10—C1	121.1 (2)	N1—C1—C10	110.8 (2)
C2—N1—C1	125.0 (2)	C9—C1—C10	112.0 (2)
C2—N1—H1	116.3 (19)	C14—C13—C12	120.6 (3)
C1—N1—H1	118.5 (19)	C14—C13—Br1	120.0 (2)
C14—C15—C10	121.6 (3)	C12—C13—Br1	119.4 (2)
C14—C15—H15A	119.2	C13—C14—C15	119.6 (3)
C10—C15—H15A	119.2	C13—C14—H14A	120.2
N2—C8—C7	122.1 (2)	C15—C14—H14A	120.2
N2—C8—C3	118.9 (2)	C5—C4—C3	121.1 (3)
C7—C8—C3	118.9 (2)	C5—C4—H4A	119.5
C6—C7—C8	120.1 (3)	C3—C4—H4A	119.5
C6—C7—H7A	120.0	C4—C5—C6	119.1 (3)
C8—C7—H7A	120.0	C4—C5—H5A	120.4
C12—C11—C10	122.0 (2)	C6—C5—H5A	120.4
C12—C11—H11A	119.0	C13—C12—C11	119.0 (3)
C10—C11—H11A	119.0	C13—C12—H12A	120.5
C4—C3—C8	119.6 (2)	C11—C12—H12A	120.5
C4—C3—C2	122.1 (2)	C7—C6—C5	121.1 (3)
C8—C3—C2	118.1 (2)	C7—C6—H6A	119.4
C1—C9—H9A	109.5	C5—C6—H6A	119.4
C1—C9—H9B	109.5
O1—C2—N1—C1	175.6 (2)	C2—N1—C1—N2	33.1 (3)
C3—C2—N1—C1	−7.2 (4)	C2—N1—C1—C9	149.4 (2)
C11—C10—C15—C14	0.6 (4)	C2—N1—C1—C10	−87.8 (3)
C1—C10—C15—C14	−176.5 (3)	C11—C10—C1—N2	−88.1 (3)
C1—N2—C8—C7	−156.5 (2)	C15—C10—C1—N2	88.9 (3)
C1—N2—C8—C3	27.8 (4)	C11—C10—C1—N1	30.5 (3)
N2—C8—C7—C6	−178.0 (3)	C15—C10—C1—N1	−152.5 (2)
C3—C8—C7—C6	−2.4 (4)	C11—C10—C1—C9	150.7 (2)
C15—C10—C11—C12	−1.2 (4)	C15—C10—C1—C9	−32.4 (3)
C1—C10—C11—C12	175.9 (2)	C12—C13—C14—C15	−0.8 (5)
N2—C8—C3—C4	178.1 (2)	Br1—C13—C14—C15	177.2 (2)
C7—C8—C3—C4	2.4 (4)	C10—C15—C14—C13	0.4 (5)
N2—C8—C3—C2	2.7 (4)	C8—C3—C4—C5	−0.8 (4)
C7—C8—C3—C2	−173.1 (2)	C2—C3—C4—C5	174.5 (3)
O1—C2—C3—C4	−11.0 (4)	C3—C4—C5—C6	−0.8 (4)
N1—C2—C3—C4	171.9 (2)	C14—C13—C12—C11	0.3 (4)
O1—C2—C3—C8	164.4 (2)	Br1—C13—C12—C11	−177.8 (2)
N1—C2—C3—C8	−12.8 (3)	C10—C11—C12—C13	0.7 (4)
C8—N2—C1—N1	−43.0 (3)	C8—C7—C6—C5	0.8 (5)
C8—N2—C1—C9	−158.8 (2)	C4—C5—C6—C7	0.8 (5)
C8—N2—C1—C10	77.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.85 (1)	2.08 (1)	2.932 (3)	179 (3)
N2—H2···O1ii	0.85 (1)	2.04 (1)	2.870 (3)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.85 (1)	2.08 (1)	2.932 (3)	179 (3)
N2—H2⋯O1ii	0.85 (1)	2.04 (1)	2.870 (3)	164 (3)

Symmetry codes: (i) ; (ii) .