2-Anilino-N-methyl-N-phenyl­benzamide

Yang, X.-X.; Zhou, C.; Qin, D.-B.

doi:10.1107/S1600536809013026

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1107

doi:10.1107/S1600536809013026

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2-Anilino-N-methyl-N-phenylbenzamide

Xing-Xing Yang,^a Chenglin Zhou ^a and Da-Bin Qin ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: qindabincwnu@yahoo.com.cn

(Received 16 March 2009; accepted 6 April 2009; online 25 April 2009)

The title compound, C₂₀H₁₈N₂O, is composed of three aromatic rings, the dihedral angles between the phenyl and benzamide rings, and between the benzamide and aniline rings being 59.86 (9) and 46.57 (10)°, respectively. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond involving the amino H atom and the benzamide carbonyl O atom. In the crystal structure, C—H⋯O and C—H⋯π interactions are present.

Related literature

For the synthesis of the title compound, see: Martín et al. (2006 ); Charton et al. (2006 ). For related structures, see: Du et al. (2009 ); Qi et al. (2002 ). For further information on molecular recognition and self-assembly, see: Brunsveld et al. (2001 ); Prins et al. (2001 ).

Experimental

Crystal data

C₂₀H₁₈N₂O
M_r = 302.36
Orthorhombic, P n a 2₁
a = 11.086 (2) Å
b = 18.150 (4) Å
c = 7.5962 (17) Å
V = 1528.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 93 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku Spider diffractometer
Absorption correction: none
12048 measured reflections
1887 independent reflections
1803 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 1.18
1887 reflections
213 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1	0.85 (2)	2.05 (2)	2.684 (2)	131.1 (18)
C9—H9⋯O1ⁱ	0.95	2.57	3.350 (2)	139
C2—H2⋯Cg2ⁱⁱ	0.95	2.75	3.420 (2)	129
C15—H15⋯Cg3ⁱⁱⁱ	0.95	2.67	3.503 (2)	147
C20—H20A⋯Cg3ⁱ	0.98	2.67	3.441 (2)	136
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) x, y, z+1; (iii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ . Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 rings, respectively.

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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/S1600536809013026/su2103sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013026/su2103Isup2.hkl

checkCIF report

Comment top

Aromatic amides have found extensive applications in preorganized rationally designed monomers for efficient molecular recognition and self-assembly (Brunsveld et al., 2001; Prins et al., 2001). Herein we report on the crystal structure of the title compound.

The bond lengths and angles in the title compound, illustrated in Fig. 1, are within normal ranges. The dihedral angles between plane (N1/C7/O1) and rings A (C1—C6), and B (C8—C13) are 56.30 (19) and 34.59 (19)°, respectively. Rings A and C (C14—C19) are inclined to one another by 14.0 (1)°, while the central ring, B, is inclined to rings A and C by 59.86 (9) and 46.57 (10)%, respectively.

The molecular structure is stabilized by an intramolecular N—H···O hydrogen bond, involving the amino (N2) H-atom and the benzamide carbonyl O-atom (O1) (Table 1). In the crystal structure symmetry related molecules are linked by a C-H···O interaction and there are also a number of C—H···π interactions present (Table 1).

Related literature top

For the synthesis of the title compound, see: Martín et al. (2006); Charton et al. (2006). For related structures, see: Du et al. (2009); Qi et al. (2002). For further information on molecular recognition and self-assembly, see: Brunsveld et al. (2001); Prins et al. (2001). Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 rings, respectively.

Experimental top

The title compound was prepared according to the reported procedure (Martín et al., 2006); Charton et al., 2006). Colourless single crystals, suitable for X-ray diffraction, were obtained by recrystallization from dichloromethane.

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); 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 of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. The intramolecular N—H···O hydrogen bond is shown as a dashed line.

2-Anilino-N-methyl-N-phenylbenzamide top

Crystal data top

C₂₀H₁₈N₂O	F(000) = 640
M_r = 302.36	D_x = 1.314 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5383 reflections
a = 11.086 (2) Å	θ = 3.3–27.5°
b = 18.150 (4) Å	µ = 0.08 mm⁻¹
c = 7.5962 (17) Å	T = 93 K
V = 1528.4 (6) Å³	Block, colorless
Z = 4	0.40 × 0.30 × 0.20 mm

Data collection top

Rigaku Spider diffractometer	1803 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 27.5°, θ_min = 3.4°
ω scans	h = −14→14
12048 measured reflections	k = −23→20
1887 independent reflections	l = −9→9

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ²(F_o²) + (0.044P)²] where P = (F_o² + 2F_c²)/3
1887 reflections	(Δ/σ)_max = 0.029
213 parameters	Δρ_max = 0.37 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O	V = 1528.4 (6) Å³
M_r = 302.36	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.086 (2) Å	µ = 0.08 mm⁻¹
b = 18.150 (4) Å	T = 93 K
c = 7.5962 (17) Å	0.40 × 0.30 × 0.20 mm

Data collection top

Rigaku Spider diffractometer	1803 reflections with I > 2σ(I)
12048 measured reflections	R_int = 0.034
1887 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.37 e Å⁻³
1887 reflections	Δρ_min = −0.18 e Å⁻³
213 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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
O1	0.31344 (11)	0.23042 (7)	0.31485 (19)	0.0223 (4)
N1	0.17863 (14)	0.22432 (8)	0.5355 (2)	0.0181 (4)
N2	0.39961 (14)	0.36734 (8)	0.2705 (2)	0.0209 (5)
C1	0.15046 (16)	0.31901 (10)	0.7624 (3)	0.0185 (5)
C2	0.08545 (17)	0.34772 (10)	0.9013 (3)	0.0214 (5)
C3	−0.02095 (17)	0.31422 (11)	0.9550 (3)	0.0227 (5)
C4	−0.06272 (17)	0.25292 (10)	0.8662 (3)	0.0236 (5)
C5	0.00131 (18)	0.22422 (10)	0.7240 (3)	0.0221 (5)
C6	0.10850 (17)	0.25700 (10)	0.6736 (2)	0.0168 (5)
C7	0.23363 (16)	0.26105 (9)	0.4024 (2)	0.0170 (5)
C8	0.19527 (16)	0.33817 (9)	0.3594 (2)	0.0167 (5)
C9	0.07452 (17)	0.35920 (9)	0.3734 (3)	0.0186 (5)
C10	0.03721 (17)	0.42992 (10)	0.3310 (3)	0.0211 (5)
C11	0.12207 (17)	0.48030 (10)	0.2705 (2)	0.0210 (5)
C12	0.24121 (17)	0.46011 (9)	0.2502 (3)	0.0199 (5)
C13	0.28079 (16)	0.38908 (10)	0.2941 (2)	0.0174 (5)
C14	0.50151 (16)	0.41172 (10)	0.2448 (3)	0.0184 (5)
C15	0.51552 (17)	0.47993 (9)	0.3279 (3)	0.0198 (5)
C16	0.61982 (17)	0.52057 (10)	0.3017 (3)	0.0207 (5)
C17	0.71193 (17)	0.49442 (10)	0.1958 (3)	0.0209 (5)
C18	0.69897 (16)	0.42597 (10)	0.1170 (3)	0.0200 (5)
C19	0.59525 (16)	0.38490 (10)	0.1413 (3)	0.0193 (5)
C20	0.21883 (19)	0.14779 (10)	0.5689 (3)	0.0233 (6)
H1	0.22390	0.34160	0.72730	0.0220*
H2	0.11360	0.39050	0.96040	0.0260*
H2N	0.4137 (18)	0.3218 (13)	0.255 (3)	0.030 (6)*
H3	−0.06480	0.33330	1.05230	0.0270*
H4	−0.13580	0.23010	0.90230	0.0280*
H5	−0.02840	0.18250	0.66220	0.0260*
H9	0.01670	0.32430	0.41300	0.0220*
H10	−0.04500	0.44370	0.34300	0.0250*
H11	0.09780	0.52910	0.24290	0.0250*
H12	0.29740	0.49490	0.20560	0.0240*
H15	0.45360	0.49840	0.40230	0.0240*
H16	0.62820	0.56720	0.35740	0.0250*
H17	0.78280	0.52280	0.17750	0.0250*
H18	0.76210	0.40710	0.04550	0.0240*
H19	0.58790	0.33800	0.08690	0.0230*
H20A	0.23570	0.12330	0.45660	0.0280*
H20B	0.15520	0.12090	0.63140	0.0280*
H20C	0.29220	0.14850	0.64090	0.0280*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0217 (6)	0.0176 (6)	0.0277 (8)	0.0002 (5)	0.0058 (6)	−0.0024 (6)
N1	0.0235 (8)	0.0128 (7)	0.0179 (8)	0.0006 (6)	0.0020 (7)	−0.0003 (6)
N2	0.0190 (8)	0.0137 (7)	0.0300 (10)	−0.0008 (6)	0.0053 (7)	−0.0012 (7)
C1	0.0189 (8)	0.0175 (8)	0.0190 (9)	−0.0007 (7)	−0.0012 (8)	0.0013 (8)
C2	0.0259 (10)	0.0198 (9)	0.0185 (9)	0.0029 (7)	−0.0031 (8)	−0.0020 (8)
C3	0.0209 (9)	0.0295 (10)	0.0177 (9)	0.0076 (8)	0.0012 (8)	0.0014 (8)
C4	0.0190 (8)	0.0326 (10)	0.0193 (10)	−0.0017 (8)	0.0004 (8)	0.0039 (9)
C5	0.0258 (9)	0.0203 (9)	0.0202 (10)	−0.0043 (7)	−0.0014 (8)	0.0007 (8)
C6	0.0203 (9)	0.0162 (8)	0.0139 (9)	0.0023 (7)	−0.0004 (8)	0.0023 (7)
C7	0.0174 (8)	0.0160 (8)	0.0175 (9)	−0.0032 (7)	−0.0013 (8)	−0.0033 (7)
C8	0.0194 (9)	0.0165 (8)	0.0142 (9)	0.0001 (7)	0.0008 (7)	−0.0007 (7)
C9	0.0183 (9)	0.0220 (9)	0.0154 (9)	−0.0023 (7)	−0.0003 (7)	−0.0001 (8)
C10	0.0190 (9)	0.0241 (9)	0.0201 (10)	0.0027 (7)	−0.0012 (8)	0.0001 (8)
C11	0.0269 (10)	0.0169 (8)	0.0193 (10)	0.0025 (7)	−0.0037 (8)	0.0014 (8)
C12	0.0243 (9)	0.0173 (9)	0.0180 (10)	−0.0043 (7)	0.0004 (8)	0.0008 (8)
C13	0.0203 (8)	0.0178 (8)	0.0140 (9)	−0.0003 (7)	0.0003 (8)	−0.0033 (7)
C14	0.0199 (8)	0.0184 (8)	0.0169 (9)	−0.0013 (7)	0.0009 (8)	0.0033 (8)
C15	0.0208 (9)	0.0197 (9)	0.0189 (9)	0.0008 (7)	0.0021 (8)	0.0005 (8)
C16	0.0248 (9)	0.0162 (8)	0.0210 (10)	−0.0016 (7)	−0.0036 (8)	−0.0004 (7)
C17	0.0184 (9)	0.0207 (9)	0.0235 (10)	−0.0023 (7)	−0.0024 (8)	0.0060 (8)
C18	0.0178 (9)	0.0216 (9)	0.0207 (10)	0.0036 (7)	0.0017 (8)	0.0041 (8)
C19	0.0220 (9)	0.0176 (8)	0.0184 (9)	0.0036 (7)	−0.0002 (8)	0.0004 (8)
C20	0.0339 (11)	0.0132 (9)	0.0227 (10)	0.0012 (8)	0.0017 (9)	0.0018 (8)

Geometric parameters (Å, º) top

O1—C7	1.239 (2)	C15—C16	1.386 (3)
N1—C6	1.434 (2)	C16—C17	1.384 (3)
N1—C7	1.356 (2)	C17—C18	1.387 (3)
N1—C20	1.481 (2)	C18—C19	1.383 (3)
N2—C13	1.387 (2)	C1—H1	0.9500
N2—C14	1.401 (2)	C2—H2	0.9500
N2—H2N	0.85 (2)	C3—H3	0.9500
C1—C2	1.380 (3)	C4—H4	0.9500
C1—C6	1.392 (3)	C5—H5	0.9500
C2—C3	1.388 (3)	C9—H9	0.9500
C3—C4	1.381 (3)	C10—H10	0.9500
C4—C5	1.394 (3)	C11—H11	0.9500
C5—C6	1.383 (3)	C12—H12	0.9500
C7—C8	1.499 (2)	C15—H15	0.9500
C8—C9	1.396 (3)	C16—H16	0.9500
C8—C13	1.414 (2)	C17—H17	0.9500
C9—C10	1.387 (3)	C18—H18	0.9500
C10—C11	1.390 (3)	C19—H19	0.9500
C11—C12	1.379 (3)	C20—H20A	0.9800
C12—C13	1.402 (2)	C20—H20B	0.9800
C14—C19	1.391 (3)	C20—H20C	0.9800
C14—C15	1.398 (3)

C6—N1—C7	125.87 (15)	C2—C1—H1	120.00
C6—N1—C20	115.20 (15)	C6—C1—H1	120.00
C7—N1—C20	116.98 (15)	C1—C2—H2	120.00
C13—N2—C14	128.34 (15)	C3—C2—H2	120.00
C14—N2—H2N	113.1 (14)	C2—C3—H3	120.00
C13—N2—H2N	118.0 (14)	C4—C3—H3	120.00
C2—C1—C6	120.08 (17)	C3—C4—H4	120.00
C1—C2—C3	120.20 (18)	C5—C4—H4	120.00
C2—C3—C4	119.6 (2)	C4—C5—H5	120.00
C3—C4—C5	120.59 (18)	C6—C5—H5	120.00
C4—C5—C6	119.44 (17)	C8—C9—H9	119.00
N1—C6—C5	119.37 (16)	C10—C9—H9	119.00
N1—C6—C1	120.51 (16)	C9—C10—H10	121.00
C1—C6—C5	120.05 (17)	C11—C10—H10	121.00
O1—C7—C8	120.32 (15)	C10—C11—H11	120.00
N1—C7—C8	119.61 (15)	C12—C11—H11	120.00
O1—C7—N1	120.06 (15)	C11—C12—H12	119.00
C9—C8—C13	119.41 (15)	C13—C12—H12	119.00
C7—C8—C9	120.71 (15)	C14—C15—H15	120.00
C7—C8—C13	119.77 (16)	C16—C15—H15	120.00
C8—C9—C10	121.43 (17)	C15—C16—H16	119.00
C9—C10—C11	118.94 (17)	C17—C16—H16	119.00
C10—C11—C12	120.68 (17)	C16—C17—H17	121.00
C11—C12—C13	121.16 (17)	C18—C17—H17	121.00
N2—C13—C8	119.76 (16)	C17—C18—H18	120.00
N2—C13—C12	121.88 (16)	C19—C18—H18	120.00
C8—C13—C12	118.33 (16)	C14—C19—H19	120.00
N2—C14—C15	122.39 (17)	C18—C19—H19	120.00
C15—C14—C19	118.82 (17)	N1—C20—H20A	109.00
N2—C14—C19	118.68 (17)	N1—C20—H20B	109.00
C14—C15—C16	119.94 (18)	N1—C20—H20C	109.00
C15—C16—C17	121.10 (18)	H20A—C20—H20B	109.00
C16—C17—C18	118.80 (17)	H20A—C20—H20C	109.00
C17—C18—C19	120.77 (18)	H20B—C20—H20C	109.00
C14—C19—C18	120.53 (18)

C7—N1—C6—C1	−46.1 (3)	N1—C7—C8—C9	−35.8 (2)
C7—N1—C6—C5	137.06 (19)	N1—C7—C8—C13	147.89 (16)
C20—N1—C6—C1	117.39 (19)	C7—C8—C9—C10	−178.79 (18)
C20—N1—C6—C5	−59.4 (2)	C13—C8—C9—C10	−2.5 (3)
C6—N1—C7—O1	163.40 (16)	C7—C8—C13—N2	−0.1 (2)
C6—N1—C7—C8	−18.0 (3)	C7—C8—C13—C12	178.12 (16)
C20—N1—C7—O1	0.1 (2)	C9—C8—C13—N2	−176.40 (16)
C20—N1—C7—C8	178.73 (15)	C9—C8—C13—C12	1.8 (2)
C14—N2—C13—C8	−164.91 (18)	C8—C9—C10—C11	1.1 (3)
C14—N2—C13—C12	17.0 (3)	C9—C10—C11—C12	1.0 (3)
C13—N2—C14—C15	35.8 (3)	C10—C11—C12—C13	−1.7 (3)
C13—N2—C14—C19	−148.16 (19)	C11—C12—C13—N2	178.41 (17)
C6—C1—C2—C3	1.1 (3)	C11—C12—C13—C8	0.3 (3)
C2—C1—C6—N1	−176.53 (17)	N2—C14—C15—C16	178.11 (19)
C2—C1—C6—C5	0.3 (3)	C19—C14—C15—C16	2.1 (3)
C1—C2—C3—C4	−1.4 (3)	N2—C14—C19—C18	−178.01 (19)
C2—C3—C4—C5	0.4 (3)	C15—C14—C19—C18	−1.9 (3)
C3—C4—C5—C6	1.0 (3)	C14—C15—C16—C17	−0.8 (3)
C4—C5—C6—N1	175.56 (17)	C15—C16—C17—C18	−0.7 (3)
C4—C5—C6—C1	−1.3 (3)	C16—C17—C18—C19	1.0 (3)
O1—C7—C8—C9	142.75 (18)	C17—C18—C19—C14	0.3 (3)
O1—C7—C8—C13	−33.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.85 (2)	2.05 (2)	2.684 (2)	131.1 (18)
C9—H9···O1ⁱ	0.95	2.57	3.350 (2)	139
C2—H2···Cg2ⁱⁱ	0.95	2.75	3.420 (2)	129
C15—H15···Cg3ⁱⁱⁱ	0.95	2.67	3.503 (2)	147
C20—H20A···Cg3ⁱ	0.98	2.67	3.441 (2)	136

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O
M_r	302.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	93
a, b, c (Å)	11.086 (2), 18.150 (4), 7.5962 (17)
V (Å³)	1528.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku Spider diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12048, 1887, 1803
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 1.18
No. of reflections	1887
No. of parameters	213
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.18

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), 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—H2N···O1	0.85 (2)	2.05 (2)	2.684 (2)	131.1 (18)
C9—H9···O1ⁱ	0.95	2.57	3.350 (2)	139
C2—H2···Cg2ⁱⁱ	0.95	2.75	3.420 (2)	129
C15—H15···Cg3ⁱⁱⁱ	0.95	2.67	3.503 (2)	147
C20—H20A···Cg3ⁱ	0.98	2.67	3.441 (2)	136

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

Acknowledgements

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039).

References

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