2-(4-Chloro-anilino)-3-(2-hydroxy-ethyl)quinazolin-4(3H)-one.

In the title mol-ecule, C(16)H(14)ClN(3)O(2), the dihedral angle between the chloro-phenyl and pyrimidinone rings is 14.8 (1)°, while the dihedral angle between the fused benzene ring and the pyrimidinone ring is 3.8 (1)°. In the crystal structure, intra-molecular N-H⋯O hydrogen bonds, together with inter-molecular O-H⋯O hydrogen-bonding inter-actions, are present.

Related literature

For the biological activities and applications of 4(3H)-quinazolinone, see: Armarego (1963 ▶); Fisnerova et al. (1986 ▶); Gravier et al. (1992 ▶). For details of our n class="Disease">ongoing heterocyclic synthesis and drug discovery project, see: Yang et al. (2008 ▶).

Experimental

Crystal data

C16H14ClN3O2

M = 315.75

Monoclinic,

a = 9.0707 (18) Å

b = 11.345 (2) Å

c = 14.143 (3) Å

β = 96.98 (3)°

V = 1444.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 273 (2) K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.947, T max = 0.973

8113 measured reflections

2824 independent reflections

2300 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.108

S = 1.05

2824 reflections

205 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶; 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: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036623/ez2147sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036623/ez2147Isup2.hkl

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

C16H14ClN3O2	F000 = 656
Mr = 315.75	Dx = 1.452 Mg m−3
Monoclinic, P21/n	Melting point = 432–434 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 9.0707 (18) Å	Cell parameters from 3170 reflections
b = 11.345 (2) Å	θ = 2.3–26.2º
c = 14.143 (3) Å	µ = 0.28 mm−1
β = 96.98 (3)º	T = 273 (2) K
V = 1444.6 (5) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.10 mm

Bruker SMART APEX CCD diffractometer	2824 independent reflections
Radiation source: fine-focus sealed tube	2300 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 273(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 2001)	h = −11→9
Tmin = 0.947, Tmax = 0.973	k = −11→13
8113 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.2177P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2824 reflections	Δρmax = 0.16 e Å−3
205 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.24608 (18)	1.06958 (14)	0.90802 (11)	0.0460 (4)
H1	0.2103	1.0780	0.8439	0.055*
C2	0.34154 (18)	1.15287 (15)	0.95164 (11)	0.0495 (4)
H2	0.3699	1.2173	0.9174	0.059*
C3	0.39474 (17)	1.13990 (14)	1.04660 (12)	0.0460 (4)
C4	0.35073 (19)	1.04650 (15)	1.09827 (12)	0.0524 (4)
H4	0.3857	1.0395	1.1626	0.063*
C5	0.25416 (18)	0.96263 (15)	1.05448 (11)	0.0502 (4)
H5	0.2242	0.8995	1.0895	0.060*
C6	0.20225 (16)	0.97305 (13)	0.95836 (11)	0.0397 (3)
C7	0.03780 (15)	0.79644 (13)	0.93558 (10)	0.0396 (3)
C8	−0.13344 (17)	0.63934 (14)	0.88093 (11)	0.0465 (4)
C9	−0.13969 (17)	0.61551 (14)	0.98083 (11)	0.0460 (4)
C10	−0.04823 (16)	0.68016 (14)	1.04878 (11)	0.0427 (4)
C11	−0.05282 (18)	0.65638 (16)	1.14562 (12)	0.0520 (4)
H11	0.0091	0.6974	1.1915	0.062*
C12	−0.1479 (2)	0.57314 (17)	1.17282 (13)	0.0608 (5)
H12	−0.1512	0.5588	1.2373	0.073*
C13	−0.2398 (2)	0.50952 (18)	1.10526 (15)	0.0672 (5)
H13	−0.3044	0.4533	1.1247	0.081*
C14	−0.2352 (2)	0.52964 (16)	1.01032 (13)	0.0607 (5)
H14	−0.2956	0.4862	0.9652	0.073*
C15	−0.00780 (19)	0.74122 (15)	0.76189 (11)	0.0477 (4)
H15A	−0.0208	0.6648	0.7312	0.057*
H15B	0.0951	0.7643	0.7613	0.057*
C16	−0.1053 (2)	0.82925 (16)	0.70402 (12)	0.0572 (4)
H16A	−0.1005	0.8163	0.6367	0.069*
H16B	−0.2076	0.8194	0.7161	0.069*
Cl1	0.51722 (6)	1.24474 (4)	1.10084 (4)	0.06868 (19)
N1	0.10834 (15)	0.89234 (12)	0.90499 (9)	0.0450 (3)
H1A	0.0750 (19)	0.9182 (16)	0.8510 (13)	0.054*
N2	−0.03685 (14)	0.72897 (11)	0.86188 (9)	0.0422 (3)
N3	0.03988 (14)	0.77194 (11)	1.02486 (9)	0.0436 (3)
O1	−0.20317 (14)	0.58621 (11)	0.81420 (9)	0.0639 (4)
O2	−0.05636 (14)	0.94472 (12)	0.72940 (9)	0.0606 (3)
H2A	−0.129 (3)	0.992 (2)	0.7132 (17)	0.091*

	U11	U22	U33	U12	U13	U23
C1	0.0555 (9)	0.0443 (9)	0.0388 (8)	−0.0021 (7)	0.0088 (7)	0.0014 (7)
C2	0.0578 (10)	0.0417 (9)	0.0510 (9)	−0.0077 (7)	0.0148 (7)	0.0012 (7)
C3	0.0454 (8)	0.0386 (8)	0.0536 (9)	−0.0025 (7)	0.0049 (7)	−0.0039 (7)
C4	0.0591 (10)	0.0470 (9)	0.0480 (9)	−0.0069 (8)	−0.0063 (7)	0.0057 (7)
C5	0.0551 (10)	0.0435 (9)	0.0493 (9)	−0.0087 (7)	−0.0040 (7)	0.0097 (7)
C6	0.0385 (8)	0.0355 (8)	0.0450 (8)	0.0015 (6)	0.0043 (6)	−0.0006 (6)
C7	0.0374 (8)	0.0374 (8)	0.0431 (8)	0.0016 (6)	0.0016 (6)	−0.0023 (6)
C8	0.0476 (9)	0.0403 (9)	0.0512 (9)	−0.0021 (7)	0.0043 (7)	−0.0092 (7)
C9	0.0481 (9)	0.0372 (8)	0.0531 (9)	−0.0018 (7)	0.0078 (7)	−0.0045 (7)
C10	0.0421 (8)	0.0391 (8)	0.0465 (8)	0.0006 (6)	0.0035 (6)	0.0020 (7)
C11	0.0526 (9)	0.0539 (10)	0.0482 (9)	−0.0061 (8)	0.0008 (7)	0.0042 (8)
C12	0.0657 (11)	0.0616 (12)	0.0556 (10)	−0.0088 (9)	0.0093 (9)	0.0124 (9)
C13	0.0748 (13)	0.0568 (12)	0.0714 (12)	−0.0225 (10)	0.0149 (10)	0.0049 (10)
C14	0.0681 (11)	0.0491 (10)	0.0654 (11)	−0.0179 (9)	0.0099 (9)	−0.0083 (9)
C15	0.0560 (10)	0.0468 (9)	0.0403 (8)	0.0042 (7)	0.0065 (7)	−0.0050 (7)
C16	0.0626 (11)	0.0598 (11)	0.0466 (9)	0.0048 (9)	−0.0035 (8)	−0.0017 (8)
Cl1	0.0759 (4)	0.0539 (3)	0.0731 (3)	−0.0218 (2)	−0.0037 (3)	−0.0055 (2)
N1	0.0489 (7)	0.0433 (8)	0.0408 (7)	−0.0053 (6)	−0.0027 (6)	0.0043 (6)
N2	0.0466 (7)	0.0386 (7)	0.0411 (7)	0.0003 (5)	0.0039 (5)	−0.0046 (5)
N3	0.0445 (7)	0.0434 (7)	0.0421 (7)	−0.0048 (5)	0.0018 (5)	0.0005 (6)
O1	0.0715 (8)	0.0628 (8)	0.0562 (7)	−0.0195 (6)	0.0029 (6)	−0.0179 (6)
O2	0.0660 (8)	0.0522 (8)	0.0596 (7)	0.0103 (6)	−0.0079 (6)	0.0050 (6)

C1—C2	1.376 (2)	C9—C14	1.400 (2)
C1—C6	1.390 (2)	C10—N3	1.3796 (19)
C1—H1	0.9300	C10—C11	1.402 (2)
C2—C3	1.379 (2)	C11—C12	1.365 (2)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.374 (2)	C12—C13	1.391 (3)
C3—Cl1	1.7408 (16)	C12—H12	0.9300
C4—C5	1.387 (2)	C13—C14	1.368 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.389 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—N2	1.476 (2)
C6—N1	1.406 (2)	C15—C16	1.508 (2)
C7—N3	1.2907 (19)	C15—H15A	0.9700
C7—N1	1.3593 (19)	C15—H15B	0.9700
C7—N2	1.400 (2)	C16—O2	1.415 (2)
C8—O1	1.2283 (19)	C16—H16A	0.9700
C8—N2	1.390 (2)	C16—H16B	0.9700
C8—C9	1.446 (2)	N1—H1A	0.839 (18)
C9—C10	1.398 (2)	O2—H2A	0.86 (2)
C2—C1—C6	120.99 (15)	C12—C11—H11	119.9
C2—C1—H1	119.5	C10—C11—H11	119.9
C6—C1—H1	119.5	C11—C12—C13	120.77 (17)
C1—C2—C3	119.35 (15)	C11—C12—H12	119.6
C1—C2—H2	120.3	C13—C12—H12	119.6
C3—C2—H2	120.3	C14—C13—C12	120.04 (17)
C4—C3—C2	120.70 (15)	C14—C13—H13	120.0
C4—C3—Cl1	120.26 (13)	C12—C13—H13	120.0
C2—C3—Cl1	119.04 (13)	C13—C14—C9	120.15 (17)
C3—C4—C5	120.01 (15)	C13—C14—H14	119.9
C3—C4—H4	120.0	C9—C14—H14	119.9
C5—C4—H4	120.0	N2—C15—C16	114.90 (14)
C4—C5—C6	119.95 (15)	N2—C15—H15A	108.5
C4—C5—H5	120.0	C16—C15—H15A	108.5
C6—C5—H5	120.0	N2—C15—H15B	108.5
C5—C6—C1	118.97 (14)	C16—C15—H15B	108.5
C5—C6—N1	125.54 (14)	H15A—C15—H15B	107.5
C1—C6—N1	115.48 (14)	O2—C16—C15	109.27 (14)
N3—C7—N1	122.16 (14)	O2—C16—H16A	109.8
N3—C7—N2	123.99 (14)	C15—C16—H16A	109.8
N1—C7—N2	113.85 (13)	O2—C16—H16B	109.8
O1—C8—N2	119.21 (15)	C15—C16—H16B	109.8
O1—C8—C9	125.53 (15)	H16A—C16—H16B	108.3
N2—C8—C9	115.25 (13)	C7—N1—C6	128.91 (13)
C10—C9—C14	119.79 (15)	C7—N1—H1A	116.0 (12)
C10—C9—C8	118.88 (14)	C6—N1—H1A	112.9 (13)
C14—C9—C8	121.33 (15)	C8—N2—C7	121.00 (13)
N3—C10—C9	122.70 (14)	C8—N2—C15	116.40 (13)
N3—C10—C11	118.15 (14)	C7—N2—C15	122.37 (13)
C9—C10—C11	119.01 (14)	C7—N3—C10	117.54 (13)
C12—C11—C10	120.22 (16)	C16—O2—H2A	107.7 (16)
C6—C1—C2—C3	0.2 (2)	C12—C13—C14—C9	−1.0 (3)
C1—C2—C3—C4	−1.5 (3)	C10—C9—C14—C13	0.4 (3)
C1—C2—C3—Cl1	179.23 (12)	C8—C9—C14—C13	−179.47 (17)
C2—C3—C4—C5	1.3 (3)	N2—C15—C16—O2	75.96 (19)
Cl1—C3—C4—C5	−179.42 (13)	N3—C7—N1—C6	6.0 (2)
C3—C4—C5—C6	0.1 (3)	N2—C7—N1—C6	−174.53 (14)
C4—C5—C6—C1	−1.4 (2)	C5—C6—N1—C7	7.1 (3)
C4—C5—C6—N1	177.75 (15)	C1—C6—N1—C7	−173.72 (14)
C2—C1—C6—C5	1.2 (2)	O1—C8—N2—C7	176.07 (14)
C2—C1—C6—N1	−178.01 (14)	C9—C8—N2—C7	−5.2 (2)
O1—C8—C9—C10	177.05 (16)	O1—C8—N2—C15	−9.3 (2)
N2—C8—C9—C10	−1.6 (2)	C9—C8—N2—C15	169.47 (13)
O1—C8—C9—C14	−3.1 (3)	N3—C7—N2—C8	9.8 (2)
N2—C8—C9—C14	178.30 (15)	N1—C7—N2—C8	−169.68 (13)
C14—C9—C10—N3	−174.93 (15)	N3—C7—N2—C15	−164.55 (14)
C8—C9—C10—N3	5.0 (2)	N1—C7—N2—C15	16.0 (2)
C14—C9—C10—C11	0.8 (2)	C16—C15—N2—C8	94.27 (17)
C8—C9—C10—C11	−179.30 (14)	C16—C15—N2—C7	−91.15 (19)
N3—C10—C11—C12	174.43 (16)	N1—C7—N3—C10	173.12 (13)
C9—C10—C11—C12	−1.5 (3)	N2—C7—N3—C10	−6.3 (2)
C10—C11—C12—C13	1.0 (3)	C9—C10—N3—C7	−1.1 (2)
C11—C12—C13—C14	0.3 (3)	C11—C10—N3—C7	−176.85 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.839 (18)	1.993 (19)	2.8017 (19)	161.8 (17)
O2—H2A···O1i	0.86 (2)	1.86 (2)	2.7180 (18)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.839 (18)	1.993 (19)	2.8017 (19)	161.8 (17)
O2—H2A⋯O1i	0.86 (2)	1.86 (2)	2.7180 (18)	174 (2)

Symmetry code: (i) .