(E)-3-[4-(Dimethyl­amino)phen­yl]-1-(4-methyl­phen­yl)prop-2-en-1-one

Wang, L.; Ma, L.-Y.; Huang, Y.-L.; Zheng, B.-Y.

doi:10.1107/S1600536809052398

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o174

doi:10.1107/S1600536809052398

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(E)-3-[4-(Dimethylamino)phenyl]-1-(4-methylphenyl)prop-2-en-1-one

Lei Wang,^a ^* Li-Ying Ma,^a Yu-Ling Huang ^a and Bai-Yu Zheng ^a

^aBinzhou Medical University, Yantai 264003, People's Republic of China
^*Correspondence e-mail: wanglei424@163.com

(Received 22 November 2009; accepted 5 December 2009; online 16 December 2009)

In the title compound, C₁₈H₁₉NO, the dihedral angle between 4-methylphenyl and 4-(dimethylamino)phenyl rings is 45.5 (3)°. The C—C=C—C torsion angle of 173.8 (3)° indicates that the molecule adopts an E configuration. The dimethylamino group is nearly coplanar with the attached benzene ring, making a dihedral angle of 2.7 (3)°. Weak intermolecular C—H⋯π interactions are observed in the crystal structure.

Related literature

The title compound is a chalcone derivative; for the biological activiy of chalcones, see: Modzelewska et al. (2006 ); Opletalova & Sedivy (1999 ); Lin et al. (2002 ); Hsieh et al. (1998 ); Lunardi et al. (2003 ); Tang et al. (2008 ). For the organic non-linear optical properties of chalcones, see: Indira et al. (2002 ); Ravindra et al. (2009 ). For related structures, see: Wang et al. (2004 ); Yang et al. (2006 ).

Experimental

Crystal data

C₁₈H₁₉NO
M_r = 265.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.276 (2) Å
b = 11.567 (3) Å
c = 17.642 (5) Å
V = 1484.8 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 193 K
0.59 × 0.35 × 0.18 mm

Data collection

Rigaku Mercury diffractometer
16704 measured reflections
1958 independent reflections
1846 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.136
S = 1.31
1958 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C11 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1ⁱ	0.95	2.94	3.697 (3)	138
C9—H9⋯Cg2ⁱⁱ	0.95	2.93	3.712 (3)	141
C16—H16B⋯Cg2ⁱⁱⁱ	0.98	2.70	3.643 (3)	161
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[-x+{\script{5\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 1999 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2000 ); 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, global. DOI: 10.1107/S1600536809052398/xu2690sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052398/xu2690Isup2.hkl

checkCIF report

Comment top

Chalcones are open chain flavonoids which consist of two substituted benzene rings bridged by a prop-2-en-1-one group. They are renowned for their broad biological activities (Opletalova & Sedivy, 1999), such as anticancer (Modzelewska et al., 2006), antitubercular (Lin et al., 2002), anti-inflammatory (Hsieh et al., 1998), trypanocidal (Lunardi et al., 2003) and antibacterial properties (Tang et al. 2008). In addition, chalcones are also finding applications as organic non-linear optical (NLO) materials for their excellent blue light transmittance and good crystal stabitily (Indira et al., 2002; Ravindra et al., 2009). As a part of our searches for NLO materials based on chalcones (Wang, et al., 2004; Yang, et al., 2006), the title compound (I) was synthesized and its crystal structure is reported. The crystal should exhibit second-order NLO properties, because it crystallizes in a non-centrosymmetric space group.

In the title compound(I) (Fig.1), the molecule adopts an E configuration with respect to C13═C14 double bond [1.340 (4) Å]: the torsion angle C1—C13—C14—C15=173.8 (3)°. The dihedral angle between the C1—C6 ring (Plane A) and the C7—C12 ring (Plane B) is 45.5 (3)°, showing the two phenyl rings are rotated oppositely with respect to the enone segment. The mean plane of C1—C13=C14—C15 (Plane C) makes dihedral angles of 8.7 (3)° and 36.7 (4)° with plane A and plane B, respectively. The phenone O1 atom deviates from plane C by 0.240 (3) Å, suggesting C=O is not coplanar with Plane C. The dimethylamino group (Plane D) is nearly coplanar with the phenyl ring to which it is bound. The dehedral angel beween plane A and plane D is 2.7 (3)°. While no classical hydrogen bonds are present, weak intermolecular C—H···π interactions are observed, which contribute to the stability of crystal packing (Table 1).

Related literature top

The title compound is a chalcone derivative; for the biological activiy of chalcones, see: Modzelewska et al. (2006); Opletalova & Sedivy (1999); Lin et al. (2002); Hsieh et al. (1998); Lunardi et al. (2003); Tang et al. (2008). For the organic non-linear optical properties of chalcones, see: Indira et al. (2002); Ravindra et al. (2009). For related structures, see: Wang et al. (2004); Yang et al. (2006).

Experimental top

The synthesis of the title compound was carried out by adding an aqueous solution of sodium hydroxide (10%, 10 ml) to a solution of 4-methylacetophenone (0.02 mol) and 4-(dimethylamino)benzaldehyde (0.02 mol). The reaction mixture was stirred for 5 h at room temperature and then neutralized with HCl solution (10%). The product was recrystallized three times from ethanol (95%). Crystals suitable for X-ray analysis were grown by slow evaporation of the acetone solution at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLEASE PROVIDE; software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids and atom labels for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis.

(E)-3-[4-(Dimethylamino)phenyl]-1-(4-methylphenyl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₉NO	F(000) = 568
M_r = 265.34	D_x = 1.187 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: p 2ac 2ab	Cell parameters from 5334 reflections
a = 7.276 (2) Å	θ = 3.0–27.5°
b = 11.567 (3) Å	µ = 0.07 mm⁻¹
c = 17.642 (5) Å	T = 193 K
V = 1484.8 (7) Å³	Block, yellow
Z = 4	0.59 × 0.35 × 0.18 mm

Data collection top

Rigaku Mercury diffractometer	1846 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.055
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
Detector resolution: 7.31 pixels mm^-1	h = −9→9
ω scans	k = −14→14
16704 measured reflections	l = −19→22
1958 independent 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.31	w = 1/[σ²(F_o²) + (0.0495P)² + 0.3222P] where P = (F_o² + 2F_c²)/3
1958 reflections	(Δ/σ)_max < 0.001
185 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₁₉NO	V = 1484.8 (7) Å³
M_r = 265.34	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.276 (2) Å	µ = 0.07 mm⁻¹
b = 11.567 (3) Å	T = 193 K
c = 17.642 (5) Å	0.59 × 0.35 × 0.18 mm

Data collection top

Rigaku Mercury diffractometer	1846 reflections with I > 2σ(I)
16704 measured reflections	R_int = 0.055
1958 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.31	Δρ_max = 0.18 e Å⁻³
1958 reflections	Δρ_min = −0.18 e Å⁻³
185 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
O1	0.9451 (4)	0.62914 (17)	0.28002 (11)	0.0570 (7)
N1	1.0052 (4)	0.9449 (2)	−0.14961 (12)	0.0474 (7)
C1	0.9388 (4)	0.8121 (2)	0.07087 (15)	0.0340 (6)
C2	1.0071 (4)	0.9237 (2)	0.05857 (14)	0.0342 (6)
H2	1.0393	0.9701	0.1010	0.041*
C3	1.0288 (4)	0.9681 (2)	−0.01345 (15)	0.0355 (6)
H3	1.0754	1.0442	−0.0195	0.043*
C4	0.9833 (4)	0.9029 (2)	−0.07801 (15)	0.0361 (6)
C5	0.9100 (4)	0.7916 (2)	−0.06585 (15)	0.0389 (6)
H5	0.8734	0.7458	−0.1079	0.047*
C6	0.8909 (4)	0.7489 (3)	0.00638 (17)	0.0377 (6)
H6	0.8431	0.6732	0.0127	0.045*
C7	0.9790 (4)	0.7943 (2)	0.35669 (14)	0.0339 (6)
C8	1.0590 (4)	0.7345 (2)	0.41698 (16)	0.0395 (6)
H8	1.1025	0.6580	0.4094	0.047*
C9	1.0757 (4)	0.7849 (2)	0.48706 (16)	0.0424 (7)
H9	1.1343	0.7435	0.5268	0.051*
C10	1.0082 (4)	0.8956 (3)	0.50109 (15)	0.0399 (6)
C11	0.9305 (4)	0.9556 (3)	0.44122 (15)	0.0410 (7)
H11	0.8854	1.0317	0.4493	0.049*
C12	0.9174 (4)	0.9066 (2)	0.36960 (15)	0.0371 (6)
H12	0.8659	0.9499	0.3291	0.045*
C13	0.9252 (4)	0.7595 (2)	0.14493 (15)	0.0370 (6)
H13	0.8853	0.6813	0.1455	0.044*
C14	0.9611 (4)	0.8060 (2)	0.21291 (14)	0.0377 (6)
H14	0.9896	0.8860	0.2163	0.045*
C15	0.9573 (4)	0.7358 (2)	0.28210 (15)	0.0382 (6)
C16	1.0849 (5)	1.0576 (3)	−0.16376 (19)	0.0606 (9)
H16A	1.2040	1.0631	−0.1381	0.091*
H16B	1.0025	1.1177	−0.1444	0.091*
H16C	1.1022	1.0681	−0.2184	0.091*
C17	0.9558 (6)	0.8769 (3)	−0.21540 (16)	0.0685 (11)
H17A	0.8250	0.8568	−0.2129	0.103*
H17B	1.0294	0.8059	−0.2164	0.103*
H17C	0.9794	0.9218	−0.2615	0.103*
C18	1.0179 (5)	0.9481 (3)	0.57936 (17)	0.0571 (9)
H18A	0.9012	0.9352	0.6058	0.086*
H18B	1.0408	1.0314	0.5751	0.086*
H18C	1.1179	0.9119	0.6080	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0875 (18)	0.0342 (10)	0.0492 (12)	−0.0048 (12)	0.0013 (13)	0.0026 (9)
N1	0.0567 (17)	0.0519 (14)	0.0335 (12)	−0.0061 (14)	0.0025 (12)	0.0008 (11)
C1	0.0297 (12)	0.0345 (12)	0.0378 (13)	−0.0005 (12)	0.0019 (11)	−0.0026 (11)
C2	0.0345 (13)	0.0343 (13)	0.0339 (13)	0.0001 (12)	−0.0010 (12)	−0.0039 (11)
C3	0.0337 (14)	0.0334 (13)	0.0394 (14)	−0.0019 (11)	−0.0012 (12)	−0.0015 (11)
C4	0.0335 (13)	0.0400 (13)	0.0348 (13)	0.0043 (12)	−0.0008 (12)	−0.0008 (11)
C5	0.0375 (14)	0.0431 (14)	0.0360 (14)	−0.0043 (13)	−0.0030 (12)	−0.0099 (12)
C6	0.0354 (14)	0.0350 (12)	0.0426 (14)	−0.0062 (12)	−0.0010 (12)	−0.0056 (11)
C7	0.0297 (13)	0.0369 (13)	0.0351 (13)	−0.0004 (12)	0.0021 (11)	0.0058 (11)
C8	0.0390 (15)	0.0337 (12)	0.0458 (15)	−0.0025 (13)	0.0022 (13)	0.0076 (12)
C9	0.0421 (15)	0.0443 (15)	0.0409 (14)	−0.0033 (14)	−0.0048 (13)	0.0132 (12)
C10	0.0346 (14)	0.0496 (15)	0.0353 (13)	−0.0105 (13)	0.0030 (12)	0.0029 (12)
C11	0.0370 (14)	0.0441 (15)	0.0418 (15)	0.0014 (13)	0.0039 (13)	−0.0037 (12)
C12	0.0351 (14)	0.0385 (13)	0.0377 (14)	0.0056 (13)	−0.0015 (12)	0.0033 (12)
C13	0.0341 (14)	0.0352 (13)	0.0416 (14)	−0.0020 (12)	0.0035 (12)	0.0000 (11)
C14	0.0420 (15)	0.0344 (13)	0.0367 (14)	−0.0035 (13)	0.0011 (12)	0.0015 (11)
C15	0.0388 (14)	0.0365 (14)	0.0393 (14)	−0.0007 (12)	0.0034 (13)	−0.0003 (12)
C16	0.060 (2)	0.072 (2)	0.0499 (18)	−0.016 (2)	0.0025 (17)	0.0142 (16)
C17	0.086 (3)	0.085 (3)	0.0346 (16)	−0.017 (2)	0.0006 (19)	−0.0049 (16)
C18	0.063 (2)	0.074 (2)	0.0347 (14)	−0.017 (2)	0.0046 (16)	−0.0016 (15)

Geometric parameters (Å, º) top

O1—C15	1.238 (3)	C9—C10	1.393 (4)
N1—C4	1.363 (3)	C9—H9	0.9500
N1—C17	1.448 (4)	C10—C11	1.385 (4)
N1—C16	1.448 (4)	C10—C18	1.510 (4)
C1—C6	1.396 (4)	C11—C12	1.388 (4)
C1—C2	1.400 (4)	C11—H11	0.9500
C1—C13	1.445 (4)	C12—H12	0.9500
C2—C3	1.380 (4)	C13—C14	1.340 (4)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.405 (4)	C14—C15	1.466 (4)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.410 (4)	C16—H16A	0.9800
C5—C6	1.374 (4)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—H6	0.9500	C17—H17A	0.9800
C7—C12	1.393 (4)	C17—H17B	0.9800
C7—C8	1.396 (4)	C17—H17C	0.9800
C7—C15	1.488 (4)	C18—H18A	0.9800
C8—C9	1.372 (4)	C18—H18B	0.9800
C8—H8	0.9500	C18—H18C	0.9800

C4—N1—C17	121.4 (3)	C10—C11—C12	121.1 (3)
C4—N1—C16	121.8 (2)	C10—C11—H11	119.4
C17—N1—C16	116.8 (2)	C12—C11—H11	119.4
C6—C1—C2	116.4 (2)	C11—C12—C7	120.5 (3)
C6—C1—C13	120.0 (2)	C11—C12—H12	119.7
C2—C1—C13	123.6 (2)	C7—C12—H12	119.7
C3—C2—C1	121.8 (2)	C14—C13—C1	128.8 (2)
C3—C2—H2	119.1	C14—C13—H13	115.6
C1—C2—H2	119.1	C1—C13—H13	115.6
C2—C3—C4	121.3 (2)	C13—C14—C15	121.3 (2)
C2—C3—H3	119.3	C13—C14—H14	119.4
C4—C3—H3	119.3	C15—C14—H14	119.4
N1—C4—C3	122.2 (2)	O1—C15—C14	121.9 (2)
N1—C4—C5	120.7 (2)	O1—C15—C7	119.1 (2)
C3—C4—C5	117.1 (2)	C14—C15—C7	118.9 (2)
C6—C5—C4	120.5 (2)	N1—C16—H16A	109.5
C6—C5—H5	119.8	N1—C16—H16B	109.5
C4—C5—H5	119.8	H16A—C16—H16B	109.5
C5—C6—C1	122.9 (3)	N1—C16—H16C	109.5
C5—C6—H6	118.6	H16A—C16—H16C	109.5
C1—C6—H6	118.6	H16B—C16—H16C	109.5
C12—C7—C8	118.1 (2)	N1—C17—H17A	109.5
C12—C7—C15	122.3 (2)	N1—C17—H17B	109.5
C8—C7—C15	119.5 (2)	H17A—C17—H17B	109.5
C9—C8—C7	120.9 (2)	N1—C17—H17C	109.5
C9—C8—H8	119.6	H17A—C17—H17C	109.5
C7—C8—H8	119.6	H17B—C17—H17C	109.5
C8—C9—C10	121.3 (3)	C10—C18—H18A	109.5
C8—C9—H9	119.4	C10—C18—H18B	109.5
C10—C9—H9	119.4	H18A—C18—H18B	109.5
C11—C10—C9	118.0 (3)	C10—C18—H18C	109.5
C11—C10—C18	121.0 (3)	H18A—C18—H18C	109.5
C9—C10—C18	121.1 (3)	H18B—C18—H18C	109.5

C6—C1—C2—C3	−1.1 (4)	C8—C9—C10—C11	−2.7 (4)
C13—C1—C2—C3	175.8 (3)	C8—C9—C10—C18	176.7 (3)
C1—C2—C3—C4	−0.1 (4)	C9—C10—C11—C12	1.0 (4)
C17—N1—C4—C3	−179.3 (3)	C18—C10—C11—C12	−178.4 (3)
C16—N1—C4—C3	3.0 (4)	C10—C11—C12—C7	1.4 (4)
C17—N1—C4—C5	−0.5 (4)	C8—C7—C12—C11	−2.0 (4)
C16—N1—C4—C5	−178.3 (3)	C15—C7—C12—C11	176.2 (3)
C2—C3—C4—N1	−179.5 (3)	C6—C1—C13—C14	−178.7 (3)
C2—C3—C4—C5	1.7 (4)	C2—C1—C13—C14	4.6 (5)
N1—C4—C5—C6	179.0 (3)	C1—C13—C14—C15	−173.8 (3)
C3—C4—C5—C6	−2.2 (4)	C13—C14—C15—O1	9.7 (5)
C4—C5—C6—C1	1.1 (4)	C13—C14—C15—C7	−173.7 (3)
C2—C1—C6—C5	0.6 (4)	C12—C7—C15—O1	−151.9 (3)
C13—C1—C6—C5	−176.4 (3)	C8—C7—C15—O1	26.3 (4)
C12—C7—C8—C9	0.3 (4)	C12—C7—C15—C14	31.4 (4)
C15—C7—C8—C9	−178.0 (3)	C8—C7—C15—C14	−150.4 (3)
C7—C8—C9—C10	2.1 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1ⁱ	0.95	2.94	3.697 (3)	138
C9—H9···Cg2ⁱⁱ	0.95	2.93	3.712 (3)	141
C16—H16B···Cg2ⁱⁱⁱ	0.98	2.70	3.643 (3)	161

Symmetry codes: (i) −x+3/2, −y+2, z−1/2; (ii) x−1/2, −y+3/2, −z+1; (iii) −x+5/2, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉NO
M_r	265.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	193
a, b, c (Å)	7.276 (2), 11.567 (3), 17.642 (5)
V (Å³)	1484.8 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.59 × 0.35 × 0.18

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16704, 1958, 1846
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.136, 1.31
No. of reflections	1958
No. of parameters	185
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLEASE PROVIDE.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1ⁱ	0.95	2.94	3.697 (3)	138
C9—H9···Cg2ⁱⁱ	0.95	2.93	3.712 (3)	141
C16—H16B···Cg2ⁱⁱⁱ	0.98	2.70	3.643 (3)	161

Symmetry codes: (i) −x+3/2, −y+2, z−1/2; (ii) x−1/2, −y+3/2, −z+1; (iii) −x+5/2, −y+2, z+1/2.

Acknowledgements

The authors are grateful to Binzhou Medical University for financial support (grant No. BY2007KJ57).

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Volume 66| Part 1| January 2010| Page o174

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