2-(2-Chloro­phen­yl)-2,3-dihydro­quinazolin-4(1H)-one

Li, M.-J.; Feng, C.-J.

doi:10.1107/S1600536809031328

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2145

doi:10.1107/S1600536809031328

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2-(2-Chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one

Ming-Jian Li ^a and Chang-Jun Feng ^a ^*

^aSchool of Chemistry & Chemical Engineering, Xuzhou Institute of Technology, Xuzhou Jiangsu 221008, People's Republic of China
^*Correspondence e-mail: feng.changjun@163.com

(Received 22 July 2009; accepted 8 August 2009; online 15 August 2009)

The title compound, C₁₄H₁₁ClN₂O, was synthesized by the reaction of 2-chlorobenzaldehyde and 2-aminobenzamide in an ionic liquid. The pyrimidine ring adopts a skew-boat conformation and the two benzene rings make a dihedral angle of 87.1 (1)°. In the crystal, N—H⋯O and C—H⋯N hydrogen bonding links the molecules along b.

Related literature

For quinazoline derivatives as antitumor agents, see: Feng et al. (2006 ); Keenan & Shakespear (2004 ); Mikiciuk-Olasik et al. (2004 ). For the biological activity of quinazoline derivatives, see: Bedi et al. (2004 ); Lin et al. (2006 ); Saleh et al. (2004 ).

Experimental

Crystal data

C₁₄H₁₁ClN₂O
M_r = 258.70
Triclinic, $[P \overline 1]$
a = 6.9900 (1) Å
b = 8.7488 (2) Å
c = 10.4756 (2) Å
α = 100.639 (1)°
β = 92.726 (1)°
γ = 101.786 (1)°
V = 613.91 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.47 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.901, T_max = 0.950
8018 measured reflections
2204 independent reflections
2029 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.082
S = 1.07
2204 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.831 (16)	2.461 (16)	3.1847 (16)	146.2 (14)
N1—H1A⋯O1ⁱⁱ	0.824 (18)	2.103 (18)	2.9146 (16)	168.4 (16)
C1—H1B⋯N2ⁱⁱⁱ	0.948 (14)	2.635 (14)	3.4369 (17)	142.6 (11)
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+2, -z; (iii) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031328/pb2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031328/pb2004Isup2.hkl

checkCIF report

Comment top

Quinazoline derivatives are well known compounds as antitumor agents (Feng et al., 2006; Keenan et al., 2004; Mikiciuk-Olasik et al., 2004). In addition, it was reported that some quinazoline derivatives possessed biological activities, such as antimalarial activity (Lin et al., 2006) antibacterial activity (Bedi et al., 2004) and antifungal activity (Saleh et al., 2004). We report here the crystal structure of 2-(2-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one, (I).

The X-ray crystal structure determination indicates that the pyrimidine ring in the quinazoline moiety is slightly distorted, adopting a skew-boat conformation. The atoms of C2, C3, C8 and N2 are coplanar, with the atoms N1 and C1 deviating from the defined plane by 0.256 (2) and 0.623 (2) Å, respectively. The basal plane is nearly parallel to the benzene ring (C3—C8), forming a dihedral angle of 5.4 (1) °. And is nearly perpendicular to the benzene ring (C9—C14), forming a dihedral angle of 87.7 (1) °. Two benzene rings make a dihedral angle of 87.1 (1) °.

The hydrogen bonds of N—H···O and C—H···N are presented in the crystal structure of (I) (Table 2). The intermolecular hydrogen bond (N1—H1A···O1) and hydrogen bond (C1—H1B···N2) link the adjacent molecules, forming dimmers, respectively. The hydrogen bond of N2—H2A···O1 and above hydrogen bonds link the molecules forming polymers along b (Figure 2).

Related literature top

For quinazoline derivatives as antitumor agents, see: Feng et al. (2006); Keenan & Shakespear (2004); Mikiciuk-Olasik et al. (2004). For the biological activity of quinazoline derivatives, see: Bedi et al. (2004); Lin et al. (2006); Saleh et al. (2004).

Experimental top

The title compound, (I), was prepared by the reaction of 2-chlorobenzaldehyde (2 mmol, 0.280 g), 2-aminobenzamide (2 mmol, 0.272 g) and ionic liquid of [Bmim]Br (2 ml) at 353 K. The isolated compound melts at 485–486 K. The single crystals suitable for X-ray diffraction were obtained by slow evaporation ethanol solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure drawing for (I) showing 50% probability of displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The molecular packing diagramshowing the hydrogen-bonding network in the crystal for (I).

2-(2-Chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one top

Crystal data top

C₁₄H₁₁ClN₂O	Z = 2
M_r = 258.70	F(000) = 268
Triclinic, P1	D_x = 1.399 Mg m⁻³
Hall symbol: -P 1	Melting point = 485–486 K
a = 6.9900 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7488 (2) Å	Cell parameters from 5614 reflections
c = 10.4756 (2) Å	θ = 2.4–27.3°
α = 100.639 (1)°	µ = 0.30 mm⁻¹
β = 92.726 (1)°	T = 296 K
γ = 101.786 (1)°	Block, colourless
V = 613.91 (2) Å³	0.47 × 0.15 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2204 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.0°
Absorption correction: multi-scan (Jacobson, 1998)	h = −8→8
T_min = 0.901, T_max = 0.950	k = −10→10
8018 measured reflections	l = −12→11

Refinement top

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0395P)² + 0.1722P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2204 reflections	Δρ_max = 0.20 e Å⁻³
176 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (4)

Crystal data top

C₁₄H₁₁ClN₂O	γ = 101.786 (1)°
M_r = 258.70	V = 613.91 (2) Å³
Triclinic, P1	Z = 2
a = 6.9900 (1) Å	Mo Kα radiation
b = 8.7488 (2) Å	µ = 0.30 mm⁻¹
c = 10.4756 (2) Å	T = 296 K
α = 100.639 (1)°	0.47 × 0.15 × 0.15 mm
β = 92.726 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2204 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2029 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.950	R_int = 0.019
8018 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.20 e Å⁻³
2204 reflections	Δρ_min = −0.19 e Å⁻³
176 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
Cl1	0.16029 (5)	0.69778 (5)	0.05650 (4)	0.05390 (17)
N2	0.50252 (18)	1.00296 (13)	0.18929 (11)	0.0344 (3)
C9	0.53903 (19)	0.72253 (15)	0.14393 (12)	0.0301 (3)
O1	1.08313 (14)	1.09067 (13)	0.17031 (11)	0.0497 (3)
C2	0.9066 (2)	1.04662 (16)	0.18541 (14)	0.0370 (3)
C8	0.61534 (19)	1.08206 (15)	0.30290 (12)	0.0319 (3)
N1	0.78205 (17)	0.94682 (14)	0.09040 (12)	0.0367 (3)
C14	0.3498 (2)	0.62845 (16)	0.12560 (13)	0.0345 (3)
C1	0.57649 (19)	0.88323 (15)	0.10227 (13)	0.0315 (3)
C10	0.6833 (2)	0.66331 (18)	0.20113 (14)	0.0411 (3)
H10A	0.8115	0.7230	0.2153	0.049*
C13	0.3048 (2)	0.48197 (17)	0.16089 (15)	0.0451 (4)
H13A	0.1769	0.4217	0.1469	0.054*
C3	0.8198 (2)	1.10531 (17)	0.30508 (13)	0.0384 (3)
C7	0.5326 (2)	1.14921 (18)	0.41197 (14)	0.0419 (3)
H7A	0.3970	1.1339	0.4120	0.050*
C11	0.6398 (3)	0.5163 (2)	0.23777 (16)	0.0521 (4)
H11A	0.7385	0.4786	0.2765	0.063*
C4	0.9362 (2)	1.1958 (2)	0.41504 (17)	0.0613 (5)
H4A	1.0720	1.2122	0.4163	0.074*
C12	0.4514 (3)	0.42650 (18)	0.21692 (16)	0.0517 (4)
H12A	0.4232	0.3277	0.2409	0.062*
C6	0.6509 (3)	1.2379 (2)	0.51937 (16)	0.0582 (5)
H6A	0.5944	1.2828	0.5916	0.070*
C5	0.8526 (3)	1.2615 (3)	0.52208 (17)	0.0722 (6)
H5A	0.9312	1.3214	0.5957	0.087*
H2A	0.382 (2)	0.9860 (18)	0.1921 (14)	0.037 (4)*
H1A	0.823 (2)	0.9236 (19)	0.0184 (18)	0.045 (4)*
H1B	0.510 (2)	0.8682 (16)	0.0185 (14)	0.027 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0326 (2)	0.0464 (2)	0.0788 (3)	0.00346 (16)	−0.01097 (18)	0.01200 (19)
N2	0.0259 (6)	0.0347 (6)	0.0423 (7)	0.0069 (5)	0.0038 (5)	0.0067 (5)
C9	0.0304 (7)	0.0324 (6)	0.0270 (6)	0.0067 (5)	0.0065 (5)	0.0041 (5)
O1	0.0298 (5)	0.0554 (7)	0.0566 (7)	−0.0007 (5)	0.0140 (5)	0.0007 (5)
C2	0.0310 (7)	0.0380 (7)	0.0418 (8)	0.0051 (6)	0.0087 (6)	0.0084 (6)
C8	0.0330 (7)	0.0308 (6)	0.0347 (7)	0.0076 (5)	0.0059 (5)	0.0119 (5)
N1	0.0338 (6)	0.0396 (6)	0.0339 (6)	0.0012 (5)	0.0126 (5)	0.0050 (5)
C14	0.0329 (7)	0.0334 (7)	0.0350 (7)	0.0055 (6)	0.0015 (5)	0.0034 (5)
C1	0.0292 (7)	0.0347 (7)	0.0298 (7)	0.0041 (5)	0.0032 (5)	0.0073 (5)
C10	0.0342 (8)	0.0447 (8)	0.0456 (8)	0.0101 (6)	0.0034 (6)	0.0105 (6)
C13	0.0473 (9)	0.0339 (7)	0.0481 (9)	−0.0027 (6)	0.0017 (7)	0.0063 (6)
C3	0.0327 (7)	0.0448 (8)	0.0368 (7)	0.0081 (6)	0.0049 (6)	0.0060 (6)
C7	0.0395 (8)	0.0473 (8)	0.0431 (8)	0.0148 (6)	0.0130 (6)	0.0118 (6)
C11	0.0576 (10)	0.0484 (9)	0.0569 (10)	0.0218 (8)	−0.0019 (8)	0.0175 (7)
C4	0.0382 (9)	0.0858 (13)	0.0502 (10)	0.0114 (9)	−0.0030 (7)	−0.0067 (9)
C12	0.0676 (11)	0.0326 (7)	0.0546 (9)	0.0063 (7)	0.0013 (8)	0.0139 (7)
C6	0.0641 (11)	0.0729 (12)	0.0372 (8)	0.0220 (9)	0.0126 (7)	0.0002 (8)
C5	0.0615 (12)	0.0989 (15)	0.0431 (10)	0.0171 (11)	−0.0070 (8)	−0.0161 (9)

Geometric parameters (Å, º) top

Cl1—C14	1.7453 (14)	C10—C11	1.388 (2)
N2—C8	1.3787 (17)	C10—H10A	0.9300
N2—C1	1.4523 (17)	C13—C12	1.372 (2)
N2—H2A	0.831 (16)	C13—H13A	0.9300
C9—C10	1.3839 (19)	C3—C4	1.388 (2)
C9—C14	1.3915 (19)	C7—C6	1.371 (2)
C9—C1	1.5240 (18)	C7—H7A	0.9300
O1—C2	1.2421 (17)	C11—C12	1.373 (2)
C2—N1	1.3405 (18)	C11—H11A	0.9300
C2—C3	1.4716 (19)	C4—C5	1.375 (2)
C8—C7	1.3924 (19)	C4—H4A	0.9300
C8—C3	1.4001 (19)	C12—H12A	0.9300
N1—C1	1.4511 (17)	C6—C5	1.380 (3)
N1—H1A	0.824 (18)	C6—H6A	0.9300
C14—C13	1.378 (2)	C5—H5A	0.9300
C1—H1B	0.948 (14)

C8—N2—C1	118.48 (11)	C11—C10—H10A	119.5
C8—N2—H2A	116.8 (10)	C12—C13—C14	118.97 (14)
C1—N2—H2A	116.0 (10)	C12—C13—H13A	120.5
C10—C9—C14	116.97 (12)	C14—C13—H13A	120.5
C10—C9—C1	123.74 (12)	C4—C3—C8	119.58 (13)
C14—C9—C1	119.28 (11)	C4—C3—C2	121.32 (14)
O1—C2—N1	121.40 (13)	C8—C3—C2	118.80 (12)
O1—C2—C3	122.54 (13)	C6—C7—C8	120.05 (14)
N1—C2—C3	116.00 (12)	C6—C7—H7A	120.0
N2—C8—C7	121.83 (12)	C8—C7—H7A	120.0
N2—C8—C3	118.83 (12)	C12—C11—C10	120.13 (14)
C7—C8—C3	119.18 (13)	C12—C11—H11A	119.9
C2—N1—C1	124.90 (12)	C10—C11—H11A	119.9
C2—N1—H1A	117.9 (12)	C5—C4—C3	120.63 (16)
C1—N1—H1A	117.1 (12)	C5—C4—H4A	119.7
C13—C14—C9	122.57 (13)	C3—C4—H4A	119.7
C13—C14—Cl1	118.17 (11)	C13—C12—C11	120.28 (14)
C9—C14—Cl1	119.26 (10)	C13—C12—H12A	119.9
N1—C1—N2	108.17 (11)	C11—C12—H12A	119.9
N1—C1—C9	113.41 (11)	C7—C6—C5	121.06 (15)
N2—C1—C9	112.80 (10)	C7—C6—H6A	119.5
N1—C1—H1B	106.9 (8)	C5—C6—H6A	119.5
N2—C1—H1B	107.8 (8)	C4—C5—C6	119.49 (16)
C9—C1—H1B	107.5 (8)	C4—C5—H5A	120.3
C9—C10—C11	121.08 (14)	C6—C5—H5A	120.3
C9—C10—H10A	119.5

C1—N2—C8—C7	−154.80 (12)	Cl1—C14—C13—C12	−179.15 (12)
C1—N2—C8—C3	29.94 (17)	N2—C8—C3—C4	174.78 (14)
O1—C2—N1—C1	176.67 (13)	C7—C8—C3—C4	−0.6 (2)
C3—C2—N1—C1	−5.9 (2)	N2—C8—C3—C2	0.93 (19)
C10—C9—C14—C13	−0.6 (2)	C7—C8—C3—C2	−174.45 (13)
C1—C9—C14—C13	−179.95 (12)	O1—C2—C3—C4	−9.3 (2)
C10—C9—C14—Cl1	178.92 (10)	N1—C2—C3—C4	173.25 (15)
C1—C9—C14—Cl1	−0.48 (16)	O1—C2—C3—C8	164.39 (14)
C2—N1—C1—N2	33.01 (17)	N1—C2—C3—C8	−13.0 (2)
C2—N1—C1—C9	−92.90 (15)	N2—C8—C7—C6	−174.73 (14)
C8—N2—C1—N1	−44.49 (15)	C3—C8—C7—C6	0.5 (2)
C8—N2—C1—C9	81.78 (14)	C9—C10—C11—C12	0.3 (2)
C10—C9—C1—N1	17.84 (18)	C8—C3—C4—C5	0.6 (3)
C14—C9—C1—N1	−162.81 (11)	C2—C3—C4—C5	174.27 (18)
C10—C9—C1—N2	−105.57 (14)	C14—C13—C12—C11	0.3 (2)
C14—C9—C1—N2	73.78 (15)	C10—C11—C12—C13	−0.6 (3)
C14—C9—C10—C11	0.2 (2)	C8—C7—C6—C5	−0.4 (3)
C1—C9—C10—C11	179.58 (13)	C3—C4—C5—C6	−0.5 (3)
C9—C14—C13—C12	0.3 (2)	C7—C6—C5—C4	0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.831 (16)	2.461 (16)	3.1847 (16)	146.2 (14)
N1—H1A···O1ⁱⁱ	0.824 (18)	2.103 (18)	2.9146 (16)	168.4 (16)
C1—H1B···N2ⁱⁱⁱ	0.948 (14)	2.635 (14)	3.4369 (17)	142.6 (11)

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+2, −z; (iii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O
M_r	258.70
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.9900 (1), 8.7488 (2), 10.4756 (2)
α, β, γ (°)	100.639 (1), 92.726 (1), 101.786 (1)
V (Å³)	613.91 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.47 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.901, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	8018, 2204, 2029
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.082, 1.07
No. of reflections	2204
No. of parameters	176
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.831 (16)	2.461 (16)	3.1847 (16)	146.2 (14)
N1—H1A···O1ⁱⁱ	0.824 (18)	2.103 (18)	2.9146 (16)	168.4 (16)
C1—H1B···N2ⁱⁱⁱ	0.948 (14)	2.635 (14)	3.4369 (17)	142.6 (11)

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+2, −z; (iii) −x+1, −y+2, −z.

Acknowledgements

We are grateful to the National Natural Science Foundation of China (20776149) and the Natural Science Foundation (XKY2008313) of Xuzhou Institute of Technology for financial support.

References

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