1-(2,6-Diiso­propyl­phen­yl)-1H-benzimidazole

Lai, S.; Chen, Y.; Li, Y.; Shen, Y.; Wu, H.

doi:10.1107/S1600536813020473

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1330

doi:10.1107/S1600536813020473

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1-(2,6-Diisopropylphenyl)-1H-benzimidazole

Sha Lai,^a ^* Yong Chen,^a Yan Li,^a Yonggang Shen ^a and Hongwei Wu ^a

^aPharmaceutical Department of The First Affiliated Hospital of Guangdong Pharmaceutical University, Clinical Pharmacy Department of Guangdong Pharmaceutical University, Guangzhou 510080, People's Republic of China
^*Correspondence e-mail: puma_0003@163.com

(Received 19 June 2013; accepted 23 July 2013; online 27 July 2013)

In the title compound, C₁₉H₂₂N₂, both the benzimidazole unit and the 2,6-diisopropylphenyl group are essentially planar [maximum deviations from the least-squares planes of 0.005 (1) and 0.009 (1) Å, respectively]. The dihedral angle between the two planes is 79.6 (7)°. In the crystal, molecules are linked into chains along the a-axis direction by weak C—H⋯N interactions. The crystal structure also features C—H⋯π interactions, which link the chains into a three-dimensional network.

Related literature

For the properties of related compounds, see: Shi et al. (2013 ); Cross et al. (1995 ); Akpinar et al. (2010 ); Wang et al. (2007 ); Mason et al. (1999 ). For bond lengths and angles in related structures, see: Jayamoorthy et al. (2013 ); Fathima et al. (2013 ); Geiger & Nellist (2013 ).

Experimental

Crystal data

C₁₉H₂₂N₂
M_r = 278.39
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.6471 (8) Å
b = 14.1216 (18) Å
c = 17.285 (2) Å
V = 1622.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 173 K
0.44 × 0.42 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.971, T_max = 0.982
9716 measured reflections
3551 independent reflections
3133 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.088
S = 1.08
3551 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C8/C9/C13–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N1ⁱ	0.95	2.47	3.4040 (18)	168
C14—H14⋯Cg3ⁱⁱ	0.95	2.68	3.5908 (16)	150
C18—H18B⋯Cg2ⁱⁱⁱ	0.98	2.79	3.5314 (17)	125
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813020473/bg2510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813020473/bg2510Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813020473/bg2510Isup3.cml

checkCIF report

Comment top

Benzimidazole is one of the most important organic intermediates in drug design, in light of the affinity it displays towards some enzymes and protein receptors (Mason et al., 1999). Our interest is focused on the design and synthesis of benzimidazole derivatives with various ancillary ligands, and their application in antioxidant activities. Herein, we report the synthesis and structure of the title compound (I). Its molecular structure is shown in Fig.1. Bond lengths and angles of the benzimidazole group are in good agreement with those observed in other benzimidazole derivatives (Jayamoorthy et al., 2013; Fathima et al., 2013; Geiger et al., 2013). Both the benzimidazole unit and the 2, 6-diisopropylphenyl groups are essentially planar (max. deviations from the L.S. plane: 0.005 (1) and 0.009 (1)Å, for atoms C7 and C9, respectively). The dihedral angle between both planes is 100.4° (7). In the crystal structure, the molecules are linked into chains along the a axis by intermolecular C—H···N hydrogen bonds (Table 1). The structure is further stabilized by weak intermolecular C—H···Cg interactions linking chains into a 3D network (Table 1 and Fig 2).

Related literature top

For the properties of related compounds, see: Shi et al. (2013); Cross et al. (1995); Akpinar et al. (2010); Wang et al. (2007), Mason et al. (1999). For bond lengths and angles in related structures, see: Jayamoorthy et al. (2013); Fathima et al. (2013); Geiger & Nellist (2013).

Experimental top

N-(2-bromophenyl)-N'-(2, 6-diisopropylphenyl)-Methanimidamide, (1.65 g, 4.58 mmol, 1 eq.) was dissolved in 18.5 ml DMSO. CuI (174 mg, 0.92 mmol, 20 mol%) and DBU (1.37 ml, 1.39 g, 9.16 mmol, 2 eq.) were added and the reaction was stirred for 3 h at 110 °C. H2O(160 ml) and acetoacetate (160 ml) were added and the layers were separated. The aqueous layer was extracted with acetoacetate (2 τimes 20 ml), the combined organic layers were dried over Na2SO4. The crude mixture was purified by column chromatography to afford the benzimidazole (1.22 g, 96%). Single crystals were grown in ethanol as a solvent at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are shown at the 40% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. Packing diagram of (I). Dashed lines indicate intermolecular hydrogen bonding interactions.

1-(2,6-Diisopropylphenyl)-1H-benzimidazole top

Crystal data top

C₁₉H₂₂N₂	F(000) = 600
M_r = 278.39	D_x = 1.140 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5376 reflections
a = 6.6471 (8) Å	θ = 2.4–27.1°
b = 14.1216 (18) Å	µ = 0.07 mm⁻¹
c = 17.285 (2) Å	T = 173 K
V = 1622.5 (4) Å³	Block, colorless
Z = 4	0.44 × 0.42 × 0.28 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3551 independent reflections
Radiation source: fine-focus sealed tube	3133 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 0 pixels mm^-1	θ_max = 27.1°, θ_min = 1.9°
phi and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −18→16
T_min = 0.971, T_max = 0.982	l = −18→22
9716 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0411P)² + 0.2264P] where P = (F_o² + 2F_c²)/3
3551 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₉H₂₂N₂	V = 1622.5 (4) Å³
M_r = 278.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.6471 (8) Å	µ = 0.07 mm⁻¹
b = 14.1216 (18) Å	T = 173 K
c = 17.285 (2) Å	0.44 × 0.42 × 0.28 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3551 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3133 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.982	R_int = 0.020
9716 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.08	Δρ_max = 0.16 e Å⁻³
3551 reflections	Δρ_min = −0.16 e Å⁻³
194 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.

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

	x	y	z	U_iso*/U_eq
C1	1.2274 (2)	0.79599 (10)	0.29080 (8)	0.0303 (3)
H1	1.2920	0.7885	0.3394	0.036*
N1	1.32623 (17)	0.80167 (9)	0.22581 (7)	0.0335 (3)
C2	1.17791 (19)	0.81252 (9)	0.17010 (8)	0.0262 (3)
N2	1.02227 (16)	0.80177 (8)	0.28307 (6)	0.0243 (2)
C3	1.1940 (2)	0.82181 (10)	0.08970 (8)	0.0327 (3)
H3	1.3217	0.8218	0.0650	0.039*
C4	1.0203 (2)	0.83093 (11)	0.04764 (8)	0.0366 (3)
H4	1.0285	0.8375	−0.0070	0.044*
C5	0.8308 (2)	0.83080 (11)	0.08327 (8)	0.0347 (3)
H5	0.7138	0.8373	0.0522	0.042*
C6	0.8096 (2)	0.82147 (10)	0.16281 (8)	0.0284 (3)
H6	0.6814	0.8211	0.1872	0.034*
C7	0.9866 (2)	0.81270 (8)	0.20455 (7)	0.0234 (3)
C8	0.87636 (19)	0.80084 (9)	0.34461 (7)	0.0227 (3)
C9	0.8510 (2)	0.88320 (9)	0.38878 (7)	0.0254 (3)
C10	0.9634 (2)	0.97431 (10)	0.37135 (8)	0.0324 (3)
H10	1.0380	0.9652	0.3217	0.039*
C11	0.8185 (3)	1.05673 (13)	0.36039 (13)	0.0604 (6)
H11A	0.7243	1.0419	0.3185	0.091*
H11B	0.8946	1.1140	0.3472	0.091*
H11C	0.7436	1.0674	0.4084	0.091*
C12	1.1172 (4)	0.99708 (15)	0.43400 (12)	0.0645 (6)
H12A	1.0480	1.0063	0.4835	0.097*
H12B	1.1898	1.0550	0.4202	0.097*
H12C	1.2127	0.9445	0.4386	0.097*
C13	0.7136 (2)	0.87915 (10)	0.44978 (8)	0.0303 (3)
H13	0.6941	0.9334	0.4815	0.036*
C14	0.6056 (2)	0.79775 (11)	0.46485 (8)	0.0315 (3)
H14	0.5136	0.7963	0.5069	0.038*
C15	0.6306 (2)	0.71811 (10)	0.41892 (8)	0.0292 (3)
H15	0.5532	0.6630	0.4292	0.035*
C16	0.76747 (19)	0.71788 (10)	0.35795 (7)	0.0249 (3)
C17	0.8059 (2)	0.62843 (10)	0.31125 (8)	0.0303 (3)
H17	0.8567	0.6479	0.2592	0.036*
C18	0.9704 (3)	0.56985 (11)	0.35044 (10)	0.0421 (4)
H18A	1.0924	0.6083	0.3557	0.063*
H18B	0.9999	0.5138	0.3189	0.063*
H18C	0.9244	0.5499	0.4018	0.063*
C19	0.6166 (3)	0.56884 (13)	0.29914 (12)	0.0534 (5)
H19A	0.5719	0.5432	0.3489	0.080*
H19B	0.6465	0.5166	0.2636	0.080*
H19C	0.5101	0.6085	0.2771	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0239 (6)	0.0333 (8)	0.0338 (7)	0.0025 (6)	−0.0026 (6)	0.0005 (6)
N1	0.0241 (6)	0.0388 (7)	0.0375 (7)	0.0032 (5)	0.0041 (5)	0.0009 (5)
C2	0.0238 (6)	0.0226 (6)	0.0324 (7)	−0.0001 (5)	0.0043 (5)	−0.0012 (5)
N2	0.0211 (5)	0.0284 (6)	0.0234 (5)	0.0027 (5)	0.0009 (4)	−0.0005 (4)
C3	0.0331 (7)	0.0323 (8)	0.0325 (7)	−0.0025 (6)	0.0124 (6)	−0.0023 (6)
C4	0.0451 (9)	0.0407 (8)	0.0239 (7)	−0.0053 (7)	0.0070 (7)	−0.0005 (6)
C5	0.0328 (8)	0.0425 (8)	0.0286 (7)	−0.0065 (7)	−0.0041 (6)	0.0019 (6)
C6	0.0232 (6)	0.0348 (8)	0.0271 (7)	−0.0021 (6)	0.0015 (5)	−0.0005 (6)
C7	0.0265 (6)	0.0193 (6)	0.0244 (6)	−0.0011 (5)	0.0041 (5)	−0.0013 (5)
C8	0.0197 (6)	0.0294 (7)	0.0189 (6)	0.0034 (5)	−0.0001 (5)	0.0015 (5)
C9	0.0260 (6)	0.0271 (7)	0.0232 (6)	0.0022 (5)	−0.0026 (5)	0.0014 (5)
C10	0.0404 (8)	0.0262 (7)	0.0305 (7)	−0.0017 (6)	0.0044 (6)	−0.0009 (5)
C11	0.0707 (13)	0.0352 (9)	0.0754 (13)	0.0121 (9)	0.0173 (11)	0.0173 (9)
C12	0.0756 (14)	0.0544 (12)	0.0634 (13)	−0.0329 (11)	−0.0177 (11)	0.0042 (9)
C13	0.0354 (7)	0.0303 (7)	0.0254 (7)	0.0052 (6)	0.0029 (6)	−0.0026 (6)
C14	0.0283 (7)	0.0431 (8)	0.0232 (7)	0.0030 (6)	0.0054 (5)	0.0025 (6)
C15	0.0271 (7)	0.0322 (7)	0.0283 (7)	−0.0034 (6)	−0.0003 (6)	0.0056 (6)
C16	0.0249 (6)	0.0274 (7)	0.0226 (6)	0.0028 (5)	−0.0039 (5)	0.0014 (5)
C17	0.0374 (8)	0.0274 (7)	0.0262 (7)	−0.0015 (6)	−0.0019 (6)	−0.0018 (5)
C18	0.0470 (10)	0.0309 (8)	0.0485 (9)	0.0066 (7)	−0.0081 (8)	−0.0062 (7)
C19	0.0466 (10)	0.0429 (10)	0.0706 (13)	−0.0067 (8)	−0.0106 (10)	−0.0192 (9)

Geometric parameters (Å, º) top

C1—N1	1.3038 (18)	C11—H11A	0.9800
C1—N2	1.3725 (16)	C11—H11B	0.9800
C1—H1	0.9500	C11—H11C	0.9800
N1—C2	1.3868 (18)	C12—H12A	0.9800
C2—C3	1.400 (2)	C12—H12B	0.9800
C2—C7	1.4044 (18)	C12—H12C	0.9800
N2—C7	1.3865 (16)	C13—C14	1.380 (2)
N2—C8	1.4396 (15)	C13—H13	0.9500
C3—C4	1.370 (2)	C14—C15	1.387 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.402 (2)	C15—C16	1.3924 (19)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.388 (2)	C16—C17	1.5207 (19)
C5—H5	0.9500	C17—C19	1.528 (2)
C6—C7	1.3857 (18)	C17—C18	1.529 (2)
C6—H6	0.9500	C17—H17	1.0000
C8—C16	1.3963 (19)	C18—H18A	0.9800
C8—C9	1.4013 (18)	C18—H18B	0.9800
C9—C13	1.3961 (19)	C18—H18C	0.9800
C9—C10	1.5181 (19)	C19—H19A	0.9800
C10—C11	1.522 (2)	C19—H19B	0.9800
C10—C12	1.524 (2)	C19—H19C	0.9800
C10—H10	1.0000

N1—C1—N2	114.39 (12)	C10—C11—H11C	109.5
N1—C1—H1	122.8	H11A—C11—H11C	109.5
N2—C1—H1	122.8	H11B—C11—H11C	109.5
C1—N1—C2	104.30 (11)	C10—C12—H12A	109.5
N1—C2—C3	130.20 (12)	C10—C12—H12B	109.5
N1—C2—C7	110.46 (11)	H12A—C12—H12B	109.5
C3—C2—C7	119.33 (12)	C10—C12—H12C	109.5
C1—N2—C7	105.78 (11)	H12A—C12—H12C	109.5
C1—N2—C8	126.64 (11)	H12B—C12—H12C	109.5
C7—N2—C8	127.52 (11)	C14—C13—C9	121.13 (13)
C4—C3—C2	118.11 (13)	C14—C13—H13	119.4
C4—C3—H3	120.9	C9—C13—H13	119.4
C2—C3—H3	120.9	C13—C14—C15	120.34 (12)
C3—C4—C5	121.57 (13)	C13—C14—H14	119.8
C3—C4—H4	119.2	C15—C14—H14	119.8
C5—C4—H4	119.2	C14—C15—C16	120.90 (13)
C6—C5—C4	121.77 (14)	C14—C15—H15	119.5
C6—C5—H5	119.1	C16—C15—H15	119.5
C4—C5—H5	119.1	C15—C16—C8	117.50 (12)
C7—C6—C5	115.96 (12)	C15—C16—C17	120.90 (12)
C7—C6—H6	122.0	C8—C16—C17	121.48 (11)
C5—C6—H6	122.0	C16—C17—C19	113.06 (12)
C6—C7—N2	131.68 (12)	C16—C17—C18	109.53 (11)
C6—C7—C2	123.26 (11)	C19—C17—C18	110.57 (13)
N2—C7—C2	105.06 (11)	C16—C17—H17	107.8
C16—C8—C9	122.96 (11)	C19—C17—H17	107.8
C16—C8—N2	118.61 (11)	C18—C17—H17	107.8
C9—C8—N2	118.43 (11)	C17—C18—H18A	109.5
C13—C9—C8	117.14 (12)	C17—C18—H18B	109.5
C13—C9—C10	120.43 (12)	H18A—C18—H18B	109.5
C8—C9—C10	122.42 (12)	C17—C18—H18C	109.5
C9—C10—C11	111.19 (13)	H18A—C18—H18C	109.5
C9—C10—C12	111.60 (13)	H18B—C18—H18C	109.5
C11—C10—C12	110.58 (15)	C17—C19—H19A	109.5
C9—C10—H10	107.8	C17—C19—H19B	109.5
C11—C10—H10	107.8	H19A—C19—H19B	109.5
C12—C10—H10	107.8	C17—C19—H19C	109.5
C10—C11—H11A	109.5	H19A—C19—H19C	109.5
C10—C11—H11B	109.5	H19B—C19—H19C	109.5
H11A—C11—H11B	109.5

N2—C1—N1—C2	0.30 (16)	C7—N2—C8—C9	−100.77 (14)
C1—N1—C2—C3	−179.65 (15)	C16—C8—C9—C13	1.78 (19)
C1—N1—C2—C7	−0.23 (15)	N2—C8—C9—C13	−177.79 (12)
N1—C1—N2—C7	−0.25 (16)	C16—C8—C9—C10	−177.13 (12)
N1—C1—N2—C8	−177.75 (12)	N2—C8—C9—C10	3.30 (18)
N1—C2—C3—C4	179.48 (14)	C13—C9—C10—C11	−54.09 (19)
C7—C2—C3—C4	0.1 (2)	C8—C9—C10—C11	124.78 (15)
C2—C3—C4—C5	−0.2 (2)	C13—C9—C10—C12	69.89 (19)
C3—C4—C5—C6	0.0 (2)	C8—C9—C10—C12	−111.24 (16)
C4—C5—C6—C7	0.2 (2)	C8—C9—C13—C14	−1.0 (2)
C5—C6—C7—N2	−179.57 (13)	C10—C9—C13—C14	177.94 (13)
C5—C6—C7—C2	−0.32 (19)	C9—C13—C14—C15	−0.5 (2)
C1—N2—C7—C6	179.44 (14)	C13—C14—C15—C16	1.4 (2)
C8—N2—C7—C6	−3.1 (2)	C14—C15—C16—C8	−0.60 (19)
C1—N2—C7—C2	0.09 (14)	C14—C15—C16—C17	175.54 (13)
C8—N2—C7—C2	177.56 (12)	C9—C8—C16—C15	−1.00 (18)
N1—C2—C7—C6	−179.34 (13)	N2—C8—C16—C15	178.57 (11)
C3—C2—C7—C6	0.16 (19)	C9—C8—C16—C17	−177.12 (12)
N1—C2—C7—N2	0.09 (14)	N2—C8—C16—C17	2.45 (18)
C3—C2—C7—N2	179.58 (12)	C15—C16—C17—C19	36.52 (19)
C1—N2—C8—C16	−103.40 (15)	C8—C16—C17—C19	−147.49 (14)
C7—N2—C8—C16	79.63 (16)	C15—C16—C17—C18	−87.28 (16)
C1—N2—C8—C9	76.19 (17)	C8—C16—C17—C18	88.71 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C8/C9/C13–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1ⁱ	0.95	2.47	3.4040 (18)	168
C14—H14···Cg3ⁱⁱ	0.95	2.68	3.5908 (16)	150
C18—H18B···Cg2ⁱⁱⁱ	0.98	2.79	3.5314 (17)	125

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+1; (iii) −x+2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C8/C9/C13–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1ⁱ	0.95	2.47	3.4040 (18)	168
C14—H14···Cg3ⁱⁱ	0.9500	2.68	3.5908 (16)	150
C18—H18B···Cg2ⁱⁱⁱ	0.9800	2.79	3.5314 (17)	125

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+1; (iii) −x+2, y−1/2, −z+1/2.

Acknowledgements

We acknowledge the Foundation for Distinguished Young Talents in Higher Education of Guangdong (No. LYM10091) for financial support.

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Volume 69| Part 8| August 2013| Page o1330

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