3-(2-Hydroxy-ethyl)-2-(p-tolyl-amino)-quinazolin-4(3H)-one.

In the title compound, C(17)H(17)N(3)O(2), the quinazolinone ring system is essentially planar. The benzene ring is twisted with respect to it by a dihedral angle of 32.7 (5)°. The mol-ecular conformation is stabilized by an N-H⋯O hydrogen bond, and the crystal structure is stabilized by inter-molecular O-H⋯N inter-actions.

Related literature

For the biological properties of quinazolinone 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, see: Yang et al. (2008 ▶). For related structures, see: Hu et al. (2006 ▶); Qu et al. (2008 ▶); Zeng et al. (2008 ▶); Sun et al. (2008 ▶).

Experimental

Crystal data

C17H17N3O2

M = 295.34

Monoclinic,

a = 7.8589 (2) Å

b = 19.1706 (5) Å

c = 10.6696 (3) Å

β = 111.082 (3)°

V = 1499.89 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.981, T max = 0.993

15404 measured reflections

2938 independent reflections

2074 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.138

S = 1.07

2938 reflections

206 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040440/bt2827sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040440/bt2827Isup2.hkl

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

C17H17N3O2	F(000) = 624
Mr = 295.34	Dx = 1.308 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2754 reflections
a = 7.8589 (2) Å	θ = 2.3–23.8°
b = 19.1706 (5) Å	µ = 0.09 mm−1
c = 10.6696 (3) Å	T = 298 K
β = 111.082 (3)°	Block, colorless
V = 1499.89 (8) Å3	0.10 × 0.10 × 0.08 mm
Z = 4

Bruker SMART 4K CCD area-detector diffractometer	2938 independent reflections
Radiation source: fine-focus sealed tube	2074 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→9
Tmin = 0.981, Tmax = 0.993	k = −23→23
15404 measured reflections	l = −13→11

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.081P)2 + 0.012P] where P = (Fo2 + 2Fc2)/3
2938 reflections	(Δ/σ)max < 0.001
206 parameters	Δρmax = 0.23 e Å−3
2 restraints	Δρmin = −0.17 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	0.713 (2)	0.6964 (7)	0.4651 (16)	0.077 (5)
H1A	0.5917	0.6810	0.4512	0.116*
H1B	0.7975	0.6738	0.5432	0.116*
H1C	0.7434	0.6846	0.3881	0.116*
C2	0.7255 (16)	0.7741 (6)	0.4853 (13)	0.053 (3)
C3	0.6939 (17)	0.8197 (6)	0.3785 (13)	0.056 (3)
H3	0.6602	0.8019	0.2918	0.068*
C4	0.7113 (16)	0.8908 (6)	0.3978 (11)	0.050 (3)
H4	0.6892	0.9202	0.3243	0.060*
C5	0.7611 (14)	0.9190 (5)	0.5253 (11)	0.042 (3)
C6	0.7883 (15)	0.8745 (6)	0.6330 (12)	0.048 (3)
H6	0.8185	0.8924	0.7193	0.058*
C7	0.7703 (16)	0.8033 (6)	0.6116 (13)	0.053 (3)
H7	0.7891	0.7740	0.6848	0.063*
C8	0.8785 (14)	1.0302 (5)	0.6438 (11)	0.041 (3)
C9	0.9600 (16)	1.1474 (6)	0.7315 (11)	0.047 (3)
C10	1.0902 (15)	1.1136 (6)	0.8487 (11)	0.044 (3)
C11	1.1021 (15)	1.0410 (6)	0.8529 (11)	0.044 (3)
C12	1.2277 (17)	1.0094 (7)	0.9662 (12)	0.059 (3)
H12	1.2365	0.9610	0.9711	0.070*
C13	1.3379 (19)	1.0490 (8)	1.0699 (13)	0.066 (4)
H13	1.4213	1.0272	1.1448	0.080*
C14	1.3277 (19)	1.1213 (7)	1.0656 (12)	0.064 (4)
H14	1.4040	1.1478	1.1366	0.077*
C15	1.2045 (18)	1.1529 (7)	0.9560 (12)	0.057 (3)
H15	1.1965	1.2013	0.9528	0.068*
C16	0.7068 (16)	1.1345 (6)	0.5175 (11)	0.049 (3)
H16A	0.6734	1.1787	0.5463	0.058*
H16B	0.5999	1.1047	0.4912	0.058*
C17	0.7589 (16)	1.1470 (6)	0.3967 (11)	0.051 (3)
H17A	0.6786	1.1817	0.3390	0.061*
H17B	0.8828	1.1645	0.4253	0.061*
N1	0.7697 (13)	0.9925 (5)	0.5361 (9)	0.048 (3)
H1	0.737 (16)	1.015 (6)	0.461 (9)	0.057*
N2	0.8506 (12)	1.1022 (4)	0.6320 (9)	0.042 (2)
N3	0.9966 (12)	0.9998 (5)	0.7464 (9)	0.046 (2)
O1	0.7451 (12)	1.0832 (4)	0.3238 (8)	0.055 (2)
H1D	0.84 (2)	1.074 (7)	0.306 (15)	0.083*
O2	0.9394 (12)	1.2106 (4)	0.7163 (9)	0.064 (3)

	U11	U22	U33	U12	U13	U23
C1	0.090 (11)	0.048 (8)	0.099 (12)	−0.014 (7)	0.040 (10)	−0.019 (7)
C2	0.049 (7)	0.045 (7)	0.068 (8)	−0.010 (5)	0.025 (6)	−0.011 (6)
C3	0.064 (8)	0.056 (7)	0.054 (8)	−0.018 (6)	0.028 (7)	−0.018 (6)
C4	0.052 (7)	0.051 (7)	0.046 (7)	−0.011 (5)	0.018 (6)	−0.003 (5)
C5	0.037 (6)	0.040 (6)	0.046 (6)	−0.009 (4)	0.013 (5)	−0.003 (5)
C6	0.051 (7)	0.047 (7)	0.046 (6)	−0.010 (5)	0.016 (6)	−0.006 (5)
C7	0.052 (8)	0.045 (7)	0.059 (8)	−0.008 (5)	0.018 (6)	0.004 (5)
C8	0.041 (6)	0.037 (6)	0.044 (6)	−0.003 (5)	0.015 (5)	−0.004 (5)
C9	0.056 (7)	0.038 (6)	0.051 (7)	−0.001 (5)	0.025 (6)	−0.008 (5)
C10	0.049 (7)	0.041 (6)	0.043 (6)	−0.004 (5)	0.020 (5)	−0.007 (5)
C11	0.045 (7)	0.045 (6)	0.040 (6)	−0.003 (5)	0.013 (5)	−0.006 (5)
C12	0.066 (8)	0.052 (7)	0.047 (7)	0.001 (6)	0.007 (6)	0.000 (5)
C13	0.065 (9)	0.075 (9)	0.045 (7)	−0.002 (7)	0.002 (7)	−0.005 (6)
C14	0.070 (9)	0.070 (9)	0.044 (7)	−0.016 (7)	0.010 (7)	−0.015 (6)
C15	0.069 (9)	0.049 (7)	0.052 (7)	−0.011 (6)	0.022 (7)	−0.014 (6)
C16	0.043 (7)	0.044 (6)	0.055 (7)	0.009 (5)	0.013 (6)	0.001 (5)
C17	0.052 (7)	0.043 (6)	0.047 (7)	0.005 (5)	0.007 (6)	0.003 (5)
N1	0.052 (6)	0.040 (5)	0.041 (5)	−0.005 (4)	0.006 (5)	0.000 (4)
N2	0.043 (5)	0.037 (5)	0.044 (5)	0.003 (4)	0.014 (4)	−0.001 (4)
N3	0.050 (6)	0.037 (5)	0.043 (5)	−0.001 (4)	0.007 (5)	−0.003 (4)
O1	0.060 (6)	0.053 (5)	0.049 (5)	0.005 (4)	0.015 (4)	−0.003 (4)
O2	0.083 (7)	0.035 (5)	0.069 (6)	0.005 (4)	0.020 (5)	−0.006 (4)

C1—C2	1.505 (17)	C10—C11	1.394 (15)
C1—H1A	0.9600	C10—C15	1.394 (15)
C1—H1B	0.9600	C11—N3	1.388 (14)
C1—H1C	0.9600	C11—C12	1.395 (16)
C2—C7	1.382 (17)	C12—C13	1.365 (17)
C2—C3	1.385 (18)	C12—H12	0.9300
C3—C4	1.380 (16)	C13—C14	1.387 (19)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.383 (15)	C14—C15	1.363 (18)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.384 (15)	C15—H15	0.9300
C5—N1	1.414 (13)	C16—N2	1.470 (14)
C6—C7	1.383 (15)	C16—C17	1.506 (16)
C6—H6	0.9300	C16—H16A	0.9700
C7—H7	0.9300	C16—H16B	0.9700
C8—N3	1.292 (14)	C17—O1	1.432 (13)
C8—N1	1.366 (14)	C17—H17A	0.9700
C8—N2	1.395 (13)	C17—H17B	0.9700
C9—O2	1.225 (13)	N1—H1	0.87 (7)
C9—N2	1.401 (14)	O1—H1D	0.88 (15)
C9—C10	1.452 (16)
C2—C1—H1A	109.5	N3—C11—C12	119.3 (10)
C2—C1—H1B	109.5	C10—C11—C12	118.7 (10)
H1A—C1—H1B	109.5	C13—C12—C11	120.4 (12)
C2—C1—H1C	109.5	C13—C12—H12	119.8
H1A—C1—H1C	109.5	C11—C12—H12	119.8
H1B—C1—H1C	109.5	C12—C13—C14	121.1 (12)
C7—C2—C3	117.0 (11)	C12—C13—H13	119.5
C7—C2—C1	121.4 (12)	C14—C13—H13	119.5
C3—C2—C1	121.5 (12)	C15—C14—C13	119.2 (11)
C4—C3—C2	121.4 (11)	C15—C14—H14	120.4
C4—C3—H3	119.3	C13—C14—H14	120.4
C2—C3—H3	119.3	C14—C15—C10	120.8 (12)
C3—C4—C5	120.7 (11)	C14—C15—H15	119.6
C3—C4—H4	119.6	C10—C15—H15	119.6
C5—C4—H4	119.6	N2—C16—C17	114.5 (9)
C4—C5—C6	118.7 (10)	N2—C16—H16A	108.6
C4—C5—N1	117.2 (10)	C17—C16—H16A	108.6
C6—C5—N1	123.9 (10)	N2—C16—H16B	108.6
C7—C6—C5	119.6 (11)	C17—C16—H16B	108.6
C7—C6—H6	120.2	H16A—C16—H16B	107.6
C5—C6—H6	120.2	O1—C17—C16	109.8 (9)
C2—C7—C6	122.4 (11)	O1—C17—H17A	109.7
C2—C7—H7	118.8	C16—C17—H17A	109.7
C6—C7—H7	118.8	O1—C17—H17B	109.7
N3—C8—N1	121.1 (10)	C16—C17—H17B	109.7
N3—C8—N2	124.4 (9)	H17A—C17—H17B	108.2
N1—C8—N2	114.6 (9)	C8—N1—C5	126.3 (9)
O2—C9—N2	119.7 (11)	C8—N1—H1	113 (9)
O2—C9—C10	125.0 (10)	C5—N1—H1	116 (8)
N2—C9—C10	115.3 (10)	C8—N2—C9	120.6 (9)
C11—C10—C15	119.8 (11)	C8—N2—C16	122.7 (9)
C11—C10—C9	119.4 (9)	C9—N2—C16	116.6 (9)
C15—C10—C9	120.8 (11)	C8—N3—C11	118.2 (9)
N3—C11—C10	121.9 (10)	C17—O1—H1D	113 (10)
C7—C2—C3—C4	1.7 (18)	C13—C14—C15—C10	0(2)
C1—C2—C3—C4	−177.7 (11)	C11—C10—C15—C14	−0.2 (18)
C2—C3—C4—C5	0.0 (18)	C9—C10—C15—C14	−179.5 (11)
C3—C4—C5—C6	−1.8 (17)	N2—C16—C17—O1	79.0 (12)
C3—C4—C5—N1	−177.9 (10)	N3—C8—N1—C5	4.7 (17)
C4—C5—C6—C7	1.8 (16)	N2—C8—N1—C5	−175.6 (9)
N1—C5—C6—C7	177.6 (10)	C4—C5—N1—C8	−152.1 (11)
C3—C2—C7—C6	−1.7 (18)	C6—C5—N1—C8	32.0 (17)
C1—C2—C7—C6	177.7 (11)	N3—C8—N2—C9	3.5 (15)
C5—C6—C7—C2	−0.1 (17)	N1—C8—N2—C9	−176.3 (9)
O2—C9—C10—C11	−179.1 (10)	N3—C8—N2—C16	−175.9 (10)
N2—C9—C10—C11	2.0 (14)	N1—C8—N2—C16	4.3 (14)
O2—C9—C10—C15	0.2 (17)	O2—C9—N2—C8	176.4 (10)
N2—C9—C10—C15	−178.7 (10)	C10—C9—N2—C8	−4.6 (14)
C15—C10—C11—N3	−177.3 (10)	O2—C9—N2—C16	−4.1 (15)
C9—C10—C11—N3	2.0 (15)	C10—C9—N2—C16	174.9 (9)
C15—C10—C11—C12	0.8 (16)	C17—C16—N2—C8	−84.7 (12)
C9—C10—C11—C12	−179.9 (10)	C17—C16—N2—C9	95.9 (11)
N3—C11—C12—C13	177.4 (12)	N1—C8—N3—C11	−179.6 (9)
C10—C11—C12—C13	−0.7 (18)	N2—C8—N3—C11	0.7 (16)
C11—C12—C13—C14	0(2)	C10—C11—N3—C8	−3.4 (16)
C12—C13—C14—C15	0(2)	C12—C11—N3—C8	178.5 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···N3i	0.88 (15)	2.09 (15)	2.882 (12)	149 (13)
N1—H1···O1	0.87 (7)	1.98 (8)	2.806 (12)	160 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯N3i	0.88 (15)	2.09 (15)	2.882 (12)	149 (13)
N1—H1⋯O1	0.87 (7)	1.98 (8)	2.806 (12)	160 (12)

Symmetry code: (i) .