2-(4-Chloro­anilino)-3-(2-hydroxy­ethyl)quinazolin-4(3H)-one

Wang, H.-L.; Yang, X.-H.; Wu, M.-H.

doi:10.1107/S1600536808036623

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2325

doi:10.1107/S1600536808036623

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2-(4-Chloroanilino)-3-(2-hydroxyethyl)quinazolin-4(3H)-one

Hong-Ling Wang,^a Xu-Hong Yang ^a and Ming-Hu Wu ^a ^*

^aFaculty of Chemistry and Life Science, Xianning University, Xianning 437100, People's Republic of China
^*Correspondence e-mail: minghuwu@hotmail.com

(Received 14 October 2008; accepted 7 November 2008; online 13 November 2008)

In the title molecule, C₁₆H₁₄ClN₃O₂, the dihedral angle between the chlorophenyl 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, intramolecular N—H⋯O hydrogen bonds, together with intermolecular O—H⋯O hydrogen-bonding interactions, 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 ongoing heterocyclic synthesis and drug discovery project, see: Yang et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₄ClN₃O₂
M_r = 315.75
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.108
S = 1.05
2824 reflections
205 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

One of the most frequently encountered heterocyclic molecules in medicinal chemistry is 4(3H)-quinazolinone, which has wide application as a result of antibacterial, antifungal, anticonvulsant, and anti-inflammatory activities (Armarego, 1963; Gravier et al., 1992; Fisnerova et al., 1986). In our ongoing heterocyclic synthesis and drug discovery project (Yang et al., 2008) we have focused on the synthesis of quinazolinones and pyrazolo pyrimidinones. Herein, the title compound was synthesized and determined by single-crystal X-ray diffraction.

In the molecule (Fig. 1), the dihedral angle between the chlorophenyl and pyrimidinone rings is 14.8 (1)°, and the dihedral angle between the fused benzene and pyrimidinone rings is 3.8 (1)°.

In the crystal structure, molecules are linked by intramolecular N1–H1A···O2 hydrogen-bonds together with O2–H2A···O1ⁱ intermolecular hydrogen-bonding interactions (symmetry code: i, -1/2 - x,1/2 + y,3/2 - z) (Fig. 2).

Related literature top

For the biologigal activites and applications of 4(3H)-quinazolinone, see: Armarego (1963); Fisnerova et al. (1986); Gravier et al. (1992). For details of our ongoing heterocyclic synthesis and drug discovery project, see: Yang et al. (2008).

Experimental top

To a solution of 2-ethoxycarbonyliminophosphorane (1.27 g, 3 mmol) in 10 ml absolute anhydrous CH₂Cl₂, 4-chlorophenylisocyanate (0.46 g, 3 mmol) was added dropwise at room temperature. The reaction mixture was left unstirred for 6 h at 273–278 K, whereafter a solution of 2-hydroxyethylamine (0.18 g, 3 mmol) in 5 ml absolute anhydrous CH₂Cl₂was added. The reaction mixture was then stirred overnight, the solution cooled and the reaction product recrystallized from CH₃OH to give colorless crystals of the title compound suitable for X-ray analysis in 58% yield.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Spek, 2003).

Figures top

	Fig. 1. View of the molecule with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed down the a axis. Hydrogen bonds are shown as dashed lines.

2-(4-Chloroanilino)-3-(2-hydroxyethyl)quinazolin-4(3H)-one top

Crystal data top

C₁₆H₁₄ClN₃O₂	F(000) = 656
M_r = 315.75	D_x = 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 = 2.3–26.2°
c = 14.143 (3) Å	µ = 0.28 mm⁻¹
β = 96.98 (3)°	T = 273 K
V = 1444.6 (5) Å³	Block, colourless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2824 independent reflections
Radiation source: fine-focus sealed tube	2300 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→9
T_min = 0.947, T_max = 0.973	k = −11→13
8113 measured reflections	l = −17→17

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0587P)² + 0.2177P] where P = (F_o² + 2F_c²)/3
2824 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₄ClN₃O₂	V = 1444.6 (5) Å³
M_r = 315.75	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.0707 (18) Å	µ = 0.28 mm⁻¹
b = 11.345 (2) Å	T = 273 K
c = 14.143 (3) Å	0.20 × 0.20 × 0.10 mm
β = 96.98 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	2824 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2300 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.973	R_int = 0.019
8113 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.16 e Å⁻³
2824 reflections	Δρ_min = −0.24 e Å⁻³
205 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x−1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄ClN₃O₂
M_r	315.75
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	9.0707 (18), 11.345 (2), 14.143 (3)
β (°)	96.98 (3)
V (Å³)	1444.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.947, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	8113, 2824, 2300
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.108, 1.05
No. of reflections	2824
No. of parameters	205
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.24

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) −x−1/2, y+1/2, −z+3/2.

Acknowledgements

We gratefully acknowledge financial support of this work as a project of the Natural Science Foundation of Hubei Province under grant No. 2006ABA334.

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