2-Anilino-3-(2-hy-droxy-phen-yl)quinazolin-4(3H)-one methanol monosolvate.

In the title compound, C(20)H(15)N(3)O(2)·CH(3)OH, the quinazolin-one ring system is approximately planar, the dihedral angle between the pyrimidinone ring and the adjacent benzene ring being 1.73 (6)°. The pyrimidinone ring makes dihedral angles of 77.58 (6) and 29.62 (6)°, respectively, with the hy-droxy-phenyl and phenyl rings. In the crystal, the components are connected by O-H⋯O and C-H⋯O hydrogen bonds, forming a zigzag chain along the b axis.

Related literature

For the biological activity of quinazoline-4(3H)-one derivatives, see: Pandeya et al. (1999 ▶); Shiba et al. (1997 ▶); Malamas & Millen (1991 ▶); Mannschreck et al. (1984 ▶); Kung et al. (1999 ▶); Bartroli et al. (1998 ▶); Palmer et al. (1997 ▶); Tsou et al. (2001 ▶); Matsuno et al. (2002 ▶). For the synthesis of the title compound, see: Yang et al. (2008 ▶).

Experimental

Crystal data

C20H15N3O2·CH4O

M = 361.39

Monoclinic,

a = 11.5575 (18) Å

b = 8.7305 (13) Å

c = 18.892 (3) Å

β = 106.251 (2)°

V = 1830.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.986, T max = 0.991

21942 measured reflections

4541 independent reflections

3087 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.02

4541 reflections

254 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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/S1600536810030631/is2582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030631/is2582Isup2.hkl

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

C20H15N3O2·CH4O	F(000) = 760
Mr = 361.39	Dx = 1.312 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6031 reflections
a = 11.5575 (18) Å	θ = 2.5–24.8°
b = 8.7305 (13) Å	µ = 0.09 mm−1
c = 18.892 (3) Å	T = 298 K
β = 106.251 (2)°	Block, colorless
V = 1830.1 (5) Å3	0.16 × 0.12 × 0.10 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	4541 independent reflections
Radiation source: fine-focus sealed tube	3087 reflections with I > 2σ(I)
graphite	Rint = 0.074
φ and ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→15
Tmin = 0.986, Tmax = 0.991	k = −11→11
21942 measured reflections	l = −25→25

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0641P)2] where P = (Fo2 + 2Fc2)/3
4541 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
C1	0.14579 (11)	0.79335 (13)	0.16728 (6)	0.0498 (3)
C2	0.02576 (10)	0.74840 (13)	0.15172 (6)	0.0489 (3)
C3	−0.05802 (12)	0.85206 (15)	0.16547 (8)	0.0596 (3)
H3	−0.1387	0.8243	0.1554	0.072*
C4	−0.02146 (14)	0.99419 (16)	0.19373 (8)	0.0689 (4)
H4	−0.0774	1.0612	0.2037	0.083*
C5	0.09758 (14)	1.03937 (16)	0.20762 (8)	0.0704 (4)
H5	0.1208	1.1371	0.2257	0.085*
C6	0.18058 (12)	0.94065 (15)	0.19480 (7)	0.0631 (4)
H6	0.2606	0.9709	0.2043	0.076*
C7	0.23377 (10)	0.68658 (14)	0.15427 (7)	0.0502 (3)
C8	0.06580 (9)	0.51041 (13)	0.11378 (6)	0.0463 (3)
C9	0.27399 (9)	0.42459 (14)	0.12439 (6)	0.0476 (3)
C10	0.33853 (10)	0.35392 (14)	0.18934 (7)	0.0511 (3)
C11	0.41817 (10)	0.23803 (15)	0.18518 (8)	0.0579 (3)
H11	0.4634	0.1906	0.2281	0.070*
C12	0.43103 (10)	0.19237 (15)	0.11810 (8)	0.0610 (3)
H12	0.4834	0.1127	0.1160	0.073*
C13	0.36727 (12)	0.26327 (16)	0.05411 (8)	0.0636 (4)
H13	0.3767	0.2321	0.0090	0.076*
C14	0.28910 (11)	0.38117 (15)	0.05734 (7)	0.0578 (3)
H14	0.2468	0.4311	0.0144	0.069*
C15	−0.07866 (10)	0.29493 (13)	0.07155 (7)	0.0489 (3)
C16	−0.10077 (12)	0.17938 (15)	0.01980 (7)	0.0595 (3)
H16	−0.0431	0.1553	−0.0042	0.071*
C17	−0.20769 (13)	0.09931 (18)	0.00341 (8)	0.0753 (4)
H17	−0.2218	0.0210	−0.0313	0.090*
C18	−0.29321 (13)	0.1351 (2)	0.03829 (11)	0.0859 (5)
H18	−0.3660	0.0823	0.0269	0.103*
C19	−0.27106 (13)	0.24912 (18)	0.09009 (11)	0.0851 (5)
H19	−0.3291	0.2726	0.1140	0.102*
C20	−0.16407 (11)	0.32979 (16)	0.10748 (9)	0.0663 (4)
H20	−0.1498	0.4066	0.1430	0.080*
C21	0.58910 (15)	0.6035 (2)	0.12019 (10)	0.0872 (5)
H21A	0.6736	0.6041	0.1238	0.131*
H21B	0.5450	0.5624	0.0733	0.131*
H21C	0.5752	0.5414	0.1589	0.131*
N1	0.18861 (7)	0.54311 (10)	0.12879 (5)	0.0475 (2)
N2	−0.01409 (8)	0.60588 (11)	0.12228 (6)	0.0514 (3)
N3	0.03525 (9)	0.36584 (12)	0.08787 (6)	0.0559 (3)
H3A	0.0925 (13)	0.3156 (15)	0.0783 (8)	0.067*
O1	0.34102 (7)	0.71482 (11)	0.16472 (5)	0.0673 (3)
O2	0.31895 (9)	0.40317 (12)	0.25304 (5)	0.0712 (3)
H2A	0.3655 (16)	0.346 (2)	0.2930 (11)	0.107*
O3	0.54980 (9)	0.75565 (12)	0.12703 (6)	0.0731 (3)
H3B	0.4742 (18)	0.750 (2)	0.1312 (11)	0.110*

	U11	U22	U33	U12	U13	U23
C1	0.0534 (7)	0.0500 (7)	0.0447 (6)	−0.0022 (5)	0.0114 (5)	0.0037 (5)
C2	0.0520 (7)	0.0475 (7)	0.0478 (6)	0.0024 (5)	0.0149 (5)	0.0089 (5)
C3	0.0614 (8)	0.0534 (8)	0.0672 (8)	0.0088 (6)	0.0233 (6)	0.0111 (6)
C4	0.0882 (11)	0.0562 (8)	0.0676 (9)	0.0171 (7)	0.0304 (8)	0.0088 (7)
C5	0.0980 (12)	0.0502 (8)	0.0643 (9)	−0.0023 (7)	0.0246 (8)	−0.0033 (6)
C6	0.0712 (9)	0.0586 (8)	0.0580 (8)	−0.0113 (7)	0.0157 (6)	−0.0035 (6)
C7	0.0442 (6)	0.0549 (7)	0.0482 (7)	−0.0061 (5)	0.0074 (5)	0.0027 (5)
C8	0.0383 (6)	0.0494 (7)	0.0498 (6)	−0.0011 (5)	0.0098 (5)	0.0041 (5)
C9	0.0338 (5)	0.0531 (7)	0.0554 (7)	−0.0019 (5)	0.0121 (5)	0.0008 (5)
C10	0.0382 (6)	0.0602 (7)	0.0555 (7)	−0.0007 (5)	0.0140 (5)	0.0028 (6)
C11	0.0407 (6)	0.0634 (8)	0.0686 (8)	0.0039 (6)	0.0136 (6)	0.0073 (7)
C12	0.0448 (7)	0.0566 (8)	0.0860 (10)	−0.0001 (6)	0.0257 (7)	−0.0024 (7)
C13	0.0612 (8)	0.0689 (9)	0.0664 (9)	−0.0030 (7)	0.0270 (7)	−0.0102 (7)
C14	0.0512 (7)	0.0654 (8)	0.0562 (8)	−0.0004 (6)	0.0140 (6)	0.0022 (6)
C15	0.0389 (6)	0.0494 (7)	0.0553 (7)	−0.0023 (5)	0.0082 (5)	0.0037 (5)
C16	0.0588 (8)	0.0675 (8)	0.0519 (7)	−0.0093 (6)	0.0148 (6)	−0.0031 (6)
C17	0.0729 (10)	0.0792 (10)	0.0674 (9)	−0.0250 (8)	0.0090 (7)	−0.0155 (8)
C18	0.0508 (8)	0.0876 (12)	0.1150 (14)	−0.0237 (8)	0.0160 (9)	−0.0126 (10)
C19	0.0535 (8)	0.0737 (10)	0.1372 (16)	−0.0113 (7)	0.0414 (9)	−0.0175 (10)
C20	0.0490 (7)	0.0605 (8)	0.0927 (11)	−0.0064 (6)	0.0253 (7)	−0.0138 (7)
C21	0.0891 (11)	0.0905 (12)	0.0887 (12)	−0.0085 (9)	0.0360 (9)	−0.0110 (9)
N1	0.0362 (5)	0.0513 (6)	0.0531 (6)	0.0001 (4)	0.0095 (4)	0.0021 (4)
N2	0.0422 (5)	0.0489 (6)	0.0629 (6)	0.0026 (4)	0.0142 (4)	0.0034 (5)
N3	0.0384 (5)	0.0523 (6)	0.0776 (7)	−0.0009 (4)	0.0173 (5)	−0.0092 (5)
O1	0.0433 (5)	0.0739 (6)	0.0811 (7)	−0.0113 (4)	0.0114 (4)	−0.0051 (5)
O2	0.0689 (6)	0.0885 (7)	0.0568 (6)	0.0236 (5)	0.0184 (5)	0.0081 (5)
O3	0.0584 (6)	0.0883 (8)	0.0715 (6)	−0.0126 (5)	0.0163 (5)	−0.0109 (5)

C1—C2	1.3917 (16)	C12—C13	1.3743 (19)
C1—C6	1.4031 (18)	C12—H12	0.9300
C1—C7	1.4502 (17)	C13—C14	1.3822 (18)
C2—N2	1.3879 (15)	C13—H13	0.9300
C2—C3	1.4017 (16)	C14—H14	0.9300
C3—C4	1.3701 (19)	C15—C16	1.3781 (17)
C3—H3	0.9300	C15—C20	1.3796 (17)
C4—C5	1.3840 (19)	C15—N3	1.4086 (14)
C4—H4	0.9300	C16—C17	1.3775 (18)
C5—C6	1.3608 (19)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.369 (2)
C6—H6	0.9300	C17—H17	0.9300
C7—O1	1.2244 (13)	C18—C19	1.369 (2)
C7—N1	1.3901 (15)	C18—H18	0.9300
C8—N2	1.2869 (14)	C19—C20	1.3804 (18)
C8—N3	1.3640 (15)	C19—H19	0.9300
C8—N1	1.3969 (13)	C20—H20	0.9300
C9—C14	1.3793 (17)	C21—O3	1.4210 (19)
C9—C10	1.3893 (17)	C21—H21A	0.9600
C9—N1	1.4482 (14)	C21—H21B	0.9600
C10—O2	1.3554 (16)	C21—H21C	0.9600
C10—C11	1.3848 (16)	N3—H3A	0.854 (14)
C11—C12	1.3755 (19)	O2—H2A	0.940 (19)
C11—H11	0.9300	O3—H3B	0.90 (2)
C2—C1—C6	120.14 (11)	C14—C13—H13	120.2
C2—C1—C7	119.19 (11)	C9—C14—C13	119.83 (12)
C6—C1—C7	120.67 (11)	C9—C14—H14	120.1
N2—C2—C1	122.47 (11)	C13—C14—H14	120.1
N2—C2—C3	118.96 (11)	C16—C15—C20	119.63 (11)
C1—C2—C3	118.57 (11)	C16—C15—N3	116.96 (11)
C4—C3—C2	120.22 (13)	C20—C15—N3	123.30 (11)
C4—C3—H3	119.9	C17—C16—C15	120.50 (13)
C2—C3—H3	119.9	C17—C16—H16	119.8
C3—C4—C5	120.92 (13)	C15—C16—H16	119.8
C3—C4—H4	119.5	C18—C17—C16	119.95 (14)
C5—C4—H4	119.5	C18—C17—H17	120.0
C6—C5—C4	119.91 (13)	C16—C17—H17	120.0
C6—C5—H5	120.0	C17—C18—C19	119.64 (13)
C4—C5—H5	120.0	C17—C18—H18	120.2
C5—C6—C1	120.22 (12)	C19—C18—H18	120.2
C5—C6—H6	119.9	C18—C19—C20	121.13 (14)
C1—C6—H6	119.9	C18—C19—H19	119.4
O1—C7—N1	120.15 (11)	C20—C19—H19	119.4
O1—C7—C1	124.71 (11)	C15—C20—C19	119.14 (13)
N1—C7—C1	115.14 (10)	C15—C20—H20	120.4
N2—C8—N3	121.42 (10)	C19—C20—H20	120.4
N2—C8—N1	124.48 (11)	O3—C21—H21A	109.5
N3—C8—N1	114.10 (10)	O3—C21—H21B	109.5
C14—C9—C10	120.95 (11)	H21A—C21—H21B	109.5
C14—C9—N1	120.83 (10)	O3—C21—H21C	109.5
C10—C9—N1	118.20 (10)	H21A—C21—H21C	109.5
O2—C10—C11	124.12 (11)	H21B—C21—H21C	109.5
O2—C10—C9	117.49 (11)	C7—N1—C8	121.07 (10)
C11—C10—C9	118.39 (12)	C7—N1—C9	117.90 (9)
C12—C11—C10	120.59 (12)	C8—N1—C9	120.82 (9)
C12—C11—H11	119.7	C8—N2—C2	117.48 (10)
C10—C11—H11	119.7	C8—N3—C15	128.13 (10)
C13—C12—C11	120.68 (12)	C8—N3—H3A	114.4 (9)
C13—C12—H12	119.7	C15—N3—H3A	117.4 (9)
C11—C12—H12	119.7	C10—O2—H2A	110.0 (11)
C12—C13—C14	119.52 (13)	C21—O3—H3B	107.3 (12)
C12—C13—H13	120.2
C6—C1—C2—N2	177.94 (11)	N3—C15—C16—C17	176.81 (12)
C7—C1—C2—N2	−1.67 (17)	C15—C16—C17—C18	0.5 (2)
C6—C1—C2—C3	−1.20 (17)	C16—C17—C18—C19	−0.9 (3)
C7—C1—C2—C3	179.18 (11)	C17—C18—C19—C20	0.5 (3)
N2—C2—C3—C4	−179.27 (11)	C16—C15—C20—C19	−0.8 (2)
C1—C2—C3—C4	−0.10 (18)	N3—C15—C20—C19	−176.97 (13)
C2—C3—C4—C5	1.5 (2)	C18—C19—C20—C15	0.4 (3)
C3—C4—C5—C6	−1.6 (2)	O1—C7—N1—C8	−177.48 (10)
C4—C5—C6—C1	0.2 (2)	C1—C7—N1—C8	3.11 (16)
C2—C1—C6—C5	1.14 (18)	O1—C7—N1—C9	7.77 (16)
C7—C1—C6—C5	−179.25 (12)	C1—C7—N1—C9	−171.63 (9)
C2—C1—C7—O1	178.64 (11)	N2—C8—N1—C7	−0.53 (17)
C6—C1—C7—O1	−0.98 (18)	N3—C8—N1—C7	178.81 (10)
C2—C1—C7—N1	−1.99 (16)	N2—C8—N1—C9	174.06 (11)
C6—C1—C7—N1	178.40 (10)	N3—C8—N1—C9	−6.60 (15)
C14—C9—C10—O2	179.84 (11)	C14—C9—N1—C7	−104.81 (13)
N1—C9—C10—O2	−1.35 (16)	C10—C9—N1—C7	76.38 (13)
C14—C9—C10—C11	−0.32 (17)	C14—C9—N1—C8	80.43 (13)
N1—C9—C10—C11	178.49 (10)	C10—C9—N1—C8	−98.38 (13)
O2—C10—C11—C12	178.59 (12)	N3—C8—N2—C2	177.48 (11)
C9—C10—C11—C12	−1.24 (17)	N1—C8—N2—C2	−3.23 (17)
C10—C11—C12—C13	1.56 (19)	C1—C2—N2—C8	4.31 (16)
C11—C12—C13—C14	−0.29 (19)	C3—C2—N2—C8	−176.55 (10)
C10—C9—C14—C13	1.57 (18)	N2—C8—N3—C15	−4.5 (2)
N1—C9—C14—C13	−177.21 (11)	N1—C8—N3—C15	176.17 (11)
C12—C13—C14—C9	−1.26 (19)	C16—C15—N3—C8	153.97 (13)
C20—C15—C16—C17	0.4 (2)	C20—C15—N3—C8	−29.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3i	0.940 (19)	1.74 (2)	2.6775 (14)	173.8 (17)
C11—H11···O1i	0.93	2.59	3.3781 (17)	143.
O3—H3B···O1	0.90 (2)	1.85 (2)	2.7237 (14)	164.1 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3i	0.940 (19)	1.74 (2)	2.6775 (14)	173.8 (17)
C11—H11⋯O1i	0.93	2.59	3.3781 (17)	143
O3—H3B⋯O1	0.90 (2)	1.85 (2)	2.7237 (14)	164.1 (18)

Symmetry code: (i) .