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

Zhang, Q.; Jiao, Y.-H.; Liu, B.; Chen, X.-M.; Ruan, M.; Xu, L.-H.

doi:10.1107/S1600536809006254

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o638

doi:10.1107/S1600536809006254

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

Qian Zhang,^a Yuan-Hong Jiao,^a ^* Bin Liu,^a Xue-Mei Chen,^a Min Ruan ^a and Ling-Hua Xu ^a

^aSchool of Chemistry and Material Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: jiaoyuanhong1995@yahoo.com.cn

(Received 26 November 2008; accepted 20 February 2009; online 28 February 2009)

The molecular and crystal structures of the title compound, C₁₆H₁₄FN₃O₂, are stabilized by intramolecular N—H⋯O and intermolecular O—H⋯O hydrogen bonds. The existence of non-classical intramolecular C—H⋯N hydrogen bonds provides a dihedral angle between the fluoro-substituted benzene and pyrimidinone rings of 7.9 (1)°.

Related literature

For the pharmacological activity of N3 and C7 disubstituted quinazolines, see: Usha et al. (2006 ). For the synthesis of quinazolinone and thienopyrimidinones, see: Yang et al. (2008 ). For synthesis, drug discovery and crystal structures, see: Yang & Wu (2008 ); Wang et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₄FN₃O₂
M_r = 299.30
Monoclinic, P 2₁ /n
a = 8.5737 (8) Å
b = 10.8268 (10) Å
c = 15.2490 (13) Å
β = 104.070(10)°
V = 1371.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 273 K
0.10 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
8342 measured reflections
2976 independent reflections
2475 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.102
S = 1.06
2976 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 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
C5—H5⋯N3	0.93	2.28	2.8807 (16)	122
N1—H1⋯O2	0.881 (9)	1.982 (10)	2.8253 (14)	159.7 (13)
O2—H2A⋯O1ⁱ	0.837 (9)	1.909 (10)	2.7426 (13)	173.6 (18)
Symmetry code: (i) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 I, global. DOI: 10.1107/S1600536809006254/rk2120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006254/rk2120Isup2.hkl

checkCIF report

Comment top

Quinazolone derivatives have evoked considerable attention in recent years as these are endowed with wide range of pharmaceutical activities. 3H–Quinazolin–4–one represents a useful nucleus for preparation of some new sedative/hypnotic and anticonvulsant agents. Of the various quinazolines reported, the N3 and C7 disubstituted quinazolines exhibit interesting pharmacological activities like analgesic, anti–inflammatory, antibacterial and anticonvulsant activities (Usha et al., 2006). In connection with our ongoing heterocyclic synthesis and drug discovery project (Yang & Wu, 2008), we have focused on the synthesis of quinazolinone and thienopyrimidinones (Wang et al., 2008; Yang et al., 2008). Herein, the title compound was synthesied and its molecular (Fig. 1) and crystal structures were determined. An intramolecular N1—H1···O2 and non–classical C5—H5···N3 hydrogen bonds provide the conformation of the molecule - dihedral angle between the fluoro–substituted benzene ring and pyrimidinone rings as 7.9 (1)°. In the crystal structure, intermolecular O2—H2a···O1ⁱ hydrogen bonds link of molecules into chains (see Tab. 1 and Fig. 2). Symmetry code: (i) -x+5/2, y-1/2, -z+1/2.

Related literature top

For the pharmacological activity of N3 and C7 disubstituted quinazolines, see: Usha et al. (2006). For the synthesis of quinazolinone and thienopyrimidinones, see: Yang et al. (2008). For synthesis, drug discovery and crystal structures, see: Yang & Wu (2008); Wang et al. (2008).

Experimental top

To a solution of 2–ethoxycarbonyliminophosphorane (1.27 g, 3.0 mmol) in 10 ml anhydrous THF, 4–fluorophenyl isocyanate (0.41 g, 3.0 mmol) was added dropwise at room temperature. The reaction mixture was left unstirred for 6 h at 273–278 K, whereafter the above resulting solution was added dropwise to a solution of ethanolamine (0.18 g, 3 mmol) in 5 ml anhydrous THF. The reaction mixture was stirred overnight at room temperature, the solvent was removed under reduced pressure and the residue was recrystallized from C₂H₄Cl₂/CH₃OH (1:1/v:v) to give colourless crystals of the title compound. Yield 89%.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. View of the title molecule with the atom–labeling scheme. Dispalcement ellipsoids are drawn at the 50% probability level. H at6oms are presented as a small spheres of arbitrary radius. Intramolecular hydrogen bonds are drawn by dashed lines.
	Fig. 2. Part of the crystal structure of the title compound showing intermolecular hydrogen bonds as dashed lines. Symmetry code: (i) -x+5/2, y-1/2, -z+1/2.

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

Crystal data top

C₁₆H₁₄FN₃O₂	F(000) = 624
M_r = 299.30	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3320 reflections
a = 8.5737 (8) Å	θ = 2.3–29.2°
b = 10.8268 (10) Å	µ = 0.11 mm⁻¹
c = 15.2490 (13) Å	T = 273 K
β = 104.407 (1)°	Block, colourless
V = 1371.0 (2) Å³	0.10 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2475 reflections with I > 2σ(I)
Radiation source: Fine–focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 27.0°, θ_min = 2.3°
ϕ and ω scans	h = −10→10
8342 measured reflections	k = −12→13
2976 independent reflections	l = −19→14

Refinement top

Refinement on F²	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: Geom
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0546P)² + 0.157P] where P = (F_o² + 2F_c²)/3
2976 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.13 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₄FN₃O₂	V = 1371.0 (2) Å³
M_r = 299.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5737 (8) Å	µ = 0.11 mm⁻¹
b = 10.8268 (10) Å	T = 273 K
c = 15.2490 (13) Å	0.10 × 0.10 × 0.10 mm
β = 104.407 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2475 reflections with I > 2σ(I)
8342 measured reflections	R_int = 0.021
2976 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.13 e Å⁻³
2976 reflections	Δρ_min = −0.24 e Å⁻³
205 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.56770 (14)	0.34529 (11)	−0.09177 (9)	0.0442 (3)
C2	0.59291 (15)	0.34162 (11)	0.00070 (9)	0.0455 (3)
H2	0.5444	0.2813	0.0283	0.055*
C3	0.69136 (15)	0.42908 (11)	0.05135 (8)	0.0427 (3)
H3	0.7096	0.4276	0.1141	0.051*
C4	0.76459 (13)	0.52003 (10)	0.01077 (8)	0.0379 (3)
C5	0.73709 (15)	0.52084 (12)	−0.08302 (8)	0.0438 (3)
H5	0.7852	0.5807	−0.1113	0.053*
C6	0.63794 (15)	0.43247 (12)	−0.13419 (8)	0.0458 (3)
H6	0.6193	0.4325	−0.1969	0.055*
C7	0.94732 (13)	0.70237 (10)	0.05017 (7)	0.0377 (3)
C8	1.13407 (14)	0.86392 (11)	0.11798 (8)	0.0418 (3)
C9	1.15360 (14)	0.88561 (11)	0.02741 (8)	0.0402 (3)
C10	1.06202 (13)	0.81559 (11)	−0.04382 (8)	0.0389 (3)
C11	1.08192 (15)	0.83508 (12)	−0.13148 (8)	0.0462 (3)
H11	1.0220	0.7892	−0.1798	0.055*
C12	1.18945 (16)	0.92159 (13)	−0.14591 (9)	0.0520 (3)
H12	1.2025	0.9334	−0.2041	0.062*
C13	1.27943 (17)	0.99209 (13)	−0.07485 (10)	0.0549 (3)
H13	1.3514	1.0510	−0.0857	0.066*
C14	1.26168 (16)	0.97446 (12)	0.01099 (10)	0.0504 (3)
H14	1.3215	1.0216	0.0586	0.060*
C15	0.97517 (16)	0.76912 (12)	0.21207 (8)	0.0450 (3)
H15A	0.8617	0.7484	0.1999	0.054*
H15B	0.9889	0.8505	0.2395	0.054*
C16	1.06872 (18)	0.67775 (13)	0.27916 (8)	0.0526 (3)
H16A	1.1828	0.6861	0.2827	0.063*
H16B	1.0521	0.6944	0.3387	0.063*
F1	0.46983 (11)	0.25850 (8)	−0.14287 (6)	0.0651 (3)
N1	0.85952 (13)	0.60633 (10)	0.07009 (7)	0.0439 (2)
H1	0.8863 (16)	0.5818 (12)	0.1269 (6)	0.053*
N2	1.02153 (12)	0.77481 (9)	0.12481 (6)	0.0393 (2)
N3	0.96041 (12)	0.72240 (9)	−0.03130 (6)	0.0411 (2)
O1	1.20713 (12)	0.91951 (9)	0.18653 (6)	0.0565 (3)
O2	1.01772 (12)	0.55593 (9)	0.25230 (6)	0.0546 (3)
H2A	1.0973 (16)	0.5093 (14)	0.2698 (12)	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0436 (6)	0.0404 (6)	0.0481 (7)	−0.0004 (5)	0.0105 (5)	−0.0022 (5)
C2	0.0492 (7)	0.0396 (6)	0.0504 (7)	0.0018 (5)	0.0174 (6)	0.0082 (5)
C3	0.0499 (7)	0.0442 (6)	0.0356 (6)	0.0072 (5)	0.0135 (5)	0.0067 (5)
C4	0.0379 (6)	0.0404 (6)	0.0360 (6)	0.0046 (5)	0.0104 (5)	0.0012 (5)
C5	0.0492 (7)	0.0480 (7)	0.0357 (6)	−0.0038 (5)	0.0132 (5)	0.0024 (5)
C6	0.0508 (7)	0.0519 (7)	0.0352 (6)	−0.0028 (6)	0.0114 (5)	−0.0017 (5)
C7	0.0370 (6)	0.0411 (6)	0.0333 (6)	0.0052 (5)	0.0058 (4)	0.0015 (5)
C8	0.0416 (6)	0.0426 (6)	0.0409 (6)	0.0040 (5)	0.0094 (5)	−0.0044 (5)
C9	0.0388 (6)	0.0399 (6)	0.0420 (6)	0.0059 (5)	0.0102 (5)	0.0020 (5)
C10	0.0377 (6)	0.0406 (6)	0.0376 (6)	0.0065 (5)	0.0080 (5)	0.0053 (5)
C11	0.0476 (7)	0.0538 (7)	0.0351 (6)	0.0046 (6)	0.0060 (5)	0.0081 (5)
C12	0.0531 (7)	0.0602 (8)	0.0442 (7)	0.0058 (6)	0.0149 (6)	0.0147 (6)
C13	0.0513 (8)	0.0542 (8)	0.0607 (9)	−0.0035 (6)	0.0168 (6)	0.0112 (7)
C14	0.0489 (7)	0.0483 (7)	0.0536 (8)	−0.0022 (6)	0.0121 (6)	−0.0010 (6)
C15	0.0535 (7)	0.0494 (7)	0.0348 (6)	0.0053 (6)	0.0160 (5)	−0.0031 (5)
C16	0.0621 (8)	0.0616 (8)	0.0327 (6)	0.0034 (6)	0.0092 (6)	−0.0009 (6)
F1	0.0736 (6)	0.0599 (5)	0.0592 (5)	−0.0229 (4)	0.0116 (4)	−0.0068 (4)
N1	0.0521 (6)	0.0494 (6)	0.0297 (5)	−0.0036 (5)	0.0092 (4)	0.0026 (4)
N2	0.0434 (5)	0.0436 (5)	0.0316 (5)	0.0037 (4)	0.0104 (4)	−0.0013 (4)
N3	0.0436 (5)	0.0456 (6)	0.0331 (5)	0.0000 (4)	0.0077 (4)	0.0028 (4)
O1	0.0601 (6)	0.0639 (6)	0.0450 (5)	−0.0115 (5)	0.0123 (4)	−0.0152 (4)
O2	0.0629 (6)	0.0552 (6)	0.0421 (5)	0.0091 (4)	0.0062 (4)	0.0055 (4)

Geometric parameters (Å, º) top

C1—C6	1.3659 (17)	C9—C14	1.4007 (17)
C1—F1	1.3670 (14)	C10—N3	1.3771 (15)
C1—C2	1.3729 (18)	C10—C11	1.4050 (16)
C2—C3	1.3716 (18)	C11—C12	1.3699 (19)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.3929 (16)	C12—C13	1.391 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.3904 (16)	C13—C14	1.3683 (19)
C4—N1	1.4098 (15)	C13—H13	0.9300
C5—C6	1.3846 (17)	C14—H14	0.9300
C5—H5	0.9300	C15—N2	1.4817 (14)
C6—H6	0.9300	C15—C16	1.5035 (18)
C7—N3	1.2932 (14)	C15—H15A	0.9700
C7—N1	1.3616 (15)	C15—H15B	0.9700
C7—N2	1.3983 (15)	C16—O2	1.4174 (17)
C8—O1	1.2335 (14)	C16—H16A	0.9700
C8—N2	1.3866 (15)	C16—H16B	0.9700
C8—C9	1.4511 (16)	N1—H1	0.881 (9)
C9—C10	1.3952 (16)	O2—H2A	0.837 (9)

C6—C1—F1	119.04 (11)	C12—C11—H11	120.0
C6—C1—C2	122.08 (12)	C10—C11—H11	120.0
F1—C1—C2	118.88 (11)	C11—C12—C13	120.99 (12)
C3—C2—C1	118.42 (11)	C11—C12—H12	119.5
C3—C2—H2	120.8	C13—C12—H12	119.5
C1—C2—H2	120.8	C14—C13—C12	119.76 (12)
C2—C3—C4	121.34 (11)	C14—C13—H13	120.1
C2—C3—H3	119.3	C12—C13—H13	120.1
C4—C3—H3	119.3	C13—C14—C9	120.19 (13)
C5—C4—C3	118.79 (11)	C13—C14—H14	119.9
C5—C4—N1	125.37 (11)	C9—C14—H14	119.9
C3—C4—N1	115.82 (10)	N2—C15—C16	114.93 (10)
C6—C5—C4	119.90 (11)	N2—C15—H15A	108.5
C6—C5—H5	120.0	C16—C15—H15A	108.5
C4—C5—H5	120.0	N2—C15—H15B	108.5
C1—C6—C5	119.46 (11)	C16—C15—H15B	108.5
C1—C6—H6	120.3	H15A—C15—H15B	107.5
C5—C6—H6	120.3	O2—C16—C15	109.98 (11)
N3—C7—N1	121.83 (11)	O2—C16—H16A	109.7
N3—C7—N2	123.86 (10)	C15—C16—H16A	109.7
N1—C7—N2	114.31 (10)	O2—C16—H16B	109.7
O1—C8—N2	119.47 (11)	C15—C16—H16B	109.7
O1—C8—C9	124.96 (11)	H16A—C16—H16B	108.2
N2—C8—C9	115.56 (10)	C7—N1—C4	128.75 (10)
C10—C9—C14	120.21 (11)	C7—N1—H1	115.3 (9)
C10—C9—C8	118.50 (11)	C4—N1—H1	113.5 (9)
C14—C9—C8	121.29 (11)	C8—N2—C7	120.89 (10)
N3—C10—C9	122.90 (10)	C8—N2—C15	116.33 (10)
N3—C10—C11	118.21 (11)	C7—N2—C15	122.56 (10)
C9—C10—C11	118.75 (11)	C7—N3—C10	117.72 (10)
C12—C11—C10	120.09 (12)	C16—O2—H2A	107.5 (13)

C6—C1—C2—C3	0.31 (19)	C12—C13—C14—C9	0.1 (2)
F1—C1—C2—C3	179.97 (10)	C10—C9—C14—C13	−0.76 (19)
C1—C2—C3—C4	0.08 (18)	C8—C9—C14—C13	179.16 (12)
C2—C3—C4—C5	−0.34 (18)	N2—C15—C16—O2	−74.18 (14)
C2—C3—C4—N1	178.41 (11)	N3—C7—N1—C4	−3.84 (19)
C3—C4—C5—C6	0.23 (18)	N2—C7—N1—C4	176.74 (11)
N1—C4—C5—C6	−178.39 (11)	C5—C4—N1—C7	−3.0 (2)
F1—C1—C6—C5	179.92 (11)	C3—C4—N1—C7	178.32 (11)
C2—C1—C6—C5	−0.42 (19)	O1—C8—N2—C7	−174.16 (11)
C4—C5—C6—C1	0.14 (19)	C9—C8—N2—C7	6.98 (16)
O1—C8—C9—C10	−179.80 (11)	O1—C8—N2—C15	11.04 (16)
N2—C8—C9—C10	−1.02 (16)	C9—C8—N2—C15	−167.81 (10)
O1—C8—C9—C14	0.28 (19)	N3—C7—N2—C8	−9.29 (17)
N2—C8—C9—C14	179.06 (11)	N1—C7—N2—C8	170.11 (10)
C14—C9—C10—N3	176.35 (11)	N3—C7—N2—C15	165.17 (11)
C8—C9—C10—N3	−3.57 (17)	N1—C7—N2—C15	−15.43 (15)
C14—C9—C10—C11	0.73 (17)	C16—C15—N2—C8	−94.13 (13)
C8—C9—C10—C11	−179.20 (10)	C16—C15—N2—C7	91.16 (14)
N3—C10—C11—C12	−175.91 (11)	N1—C7—N3—C10	−174.89 (10)
C9—C10—C11—C12	−0.08 (18)	N2—C7—N3—C10	4.47 (17)
C10—C11—C12—C13	−0.6 (2)	C9—C10—N3—C7	1.96 (17)
C11—C12—C13—C14	0.5 (2)	C11—C10—N3—C7	177.61 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N3	0.93	2.28	2.8807 (16)	122
N1—H1···O2	0.88 (1)	1.98 (1)	2.8253 (14)	160 (1)
O2—H2A···O1ⁱ	0.84 (1)	1.91 (1)	2.7426 (13)	174 (2)

Symmetry code: (i) −x+5/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄FN₃O₂
M_r	299.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	8.5737 (8), 10.8268 (10), 15.2490 (13)
β (°)	104.407 (1)
V (Å³)	1371.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8342, 2976, 2475
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.102, 1.06
No. of reflections	2976
No. of parameters	205
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.24

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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
C5—H5···N3	0.93	2.28	2.8807 (16)	122.0
N1—H1···O2	0.881 (9)	1.982 (10)	2.8253 (14)	159.7 (13)
O2—H2A···O1ⁱ	0.837 (9)	1.909 (10)	2.7426 (13)	173.6 (18)

Symmetry code: (i) −x+5/2, y−1/2, −z+1/2.

Acknowledgements

We acknowledge financial support by the Huangshi Institute of Technology (grant Nos. 08yjz23B & 07yjz18B), P. R. China.

References

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