metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890
Volume 65| Part 10| October 2009| Pages m1226-m1227

{4-Bromo-2-[2-(piperidin-1-ium-1yl)ethyl­iminometh­yl]phenolato}di­iodido­zinc(II)

aKey Laboratory of Surface and Interface Science of Henan, School of Materials and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
*Correspondence e-mail: xuewen-zhu@163.com

(Received 10 September 2009; accepted 14 September 2009; online 19 September 2009)

In the title complex, [ZnI2(C14H19BrN2O)], the ZnII atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand and by two iodide ions in a distorted tetra­hedral coordination. In the crystal structure, mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For background to the chemistry of Schiff base complexes, see: Ali et al. (2008[Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718-m719.]); Biswas et al. (2008[Biswas, C., Drew, M. G. B. & Ghosh, A. (2008). Inorg. Chem. 47, 4513-4519.]); Chen et al. (2008[Chen, Z., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170-2171.]); Darensbourg & Frantz (2007[Darensbourg, D. J. & Frantz, E. B. (2007). Inorg. Chem. 46, 5967-5978.]); Habibi et al. (2007[Habibi, M. H., Askari, E., Chantrapromma, S. & Fun, H.-K. (2007). Acta Cryst. E63, m2905-m2906.]); Kawamoto et al. (2008[Kawamoto, T., Nishiwaki, M., Tsunekawa, Y., Nozaki, K. & Konno, T. (2008). Inorg. Chem. 47, 3095-3104.]); Lipscomb & Sträter (1996[Lipscomb, W. N. & Sträter, N. (1996). Chem. Rev. 96, 2375-2434.]); Tomat et al. (2007[Tomat, E., Cuesta, L., Lynch, V. M. & Sessler, J. L. (2007). Inorg. Chem. 46, 6224-6226.]); Wu et al. (2008[Wu, J.-C., Liu, S.-X., Keene, T. D., Neels, A., Mereacre, V., Powell, A. K. & Decurtins, S. (2008). Inorg. Chem. 47, 3452-3459.]); Yuan et al. (2007[Yuan, M., Zhao, F., Zhang, W., WAng, Z.-M. & Gao, S. (2007). Inorg. Chem. 46, 11235-11242.]). For related structures, see: Zhu (2008[Zhu, X.-W. (2008). Acta Cryst. E64, m1456-m1457.]); Zhu & Yang (2008a[Zhu, X.-W. & Yang, X.-Z. (2008a). Acta Cryst. E64, m1090-m1091.],b[Zhu, X.-W. & Yang, X.-Z. (2008b). Acta Cryst. E64, m1092-m1093.],c[Zhu, X.-W. & Yang, X.-Z. (2008c). Acta Cryst. E64, m1094-m1095.]); Qiu (2006a[Qiu, X.-Y. (2006a). Acta Cryst. E62, m717-m718.],b[Qiu, X.-Y. (2006b). Acta Cryst. E62, m2173-m2174.]); Wei et al. (2007[Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2007). Acta Cryst. E63, m654-m655.]); Zhu et al. (2007[Zhu, Q.-Y., Wei, Y.-J. & Wang, F.-W. (2007). Acta Cryst. E63, m1431-m1432.]).

[Scheme 1]

Experimental

Crystal data
  • [ZnI2(C14H19BrN2O)]

  • Mr = 630.39

  • Monoclinic, P 21 /n

  • a = 10.470 (3) Å

  • b = 12.351 (3) Å

  • c = 15.426 (4) Å

  • β = 102.326 (3)°

  • V = 1948.8 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 6.48 mm−1

  • T = 298 K

  • 0.17 × 0.15 × 0.15 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.406, Tmax = 0.443

  • 14478 measured reflections

  • 4193 independent reflections

  • 2953 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.093

  • S = 1.03

  • 4193 reflections

  • 193 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.68 e Å−3

  • Δρmin = −1.09 e Å−3

Table 1
Selected geometric parameters (Å, °)

Zn1—O1 1.981 (4)
Zn1—N1 2.047 (4)
Zn1—I2 2.5428 (9)
Zn1—I1 2.5771 (9)
O1—Zn1—N1 91.61 (16)
O1—Zn1—I2 114.27 (10)
N1—Zn1—I2 113.47 (12)
O1—Zn1—I1 109.08 (12)
N1—Zn1—I1 108.67 (12)
I2—Zn1—I1 116.86 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O1i 0.90 (5) 1.85 (5) 2.745 (6) 176 (7)
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Schiff bases have widely been used as versatile ligands in coordination chemistry (Biswas et al., 2008; Wu et al., 2008; Kawamoto et al., 2008; Ali et al., 2008; Habibi et al., 2007), and their metal complexes are of great interest in many fields (Chen et al., 2008; Yuan et al., 2007; Tomat et al., 2007; Darensbourg & Frantz, 2007). Zinc(II) is an important element in biological systems and functions as the active site of hydrolytic enzymes, such as carboxypeptidase and carbonic anhydrase where it is in a hard-donor coordination environment of nitrogen and oxygen ligands (Lipscomb & Sträter, 1996). Recently, we have reported a few Schiff base zinc complexes (Zhu, 2008; Zhu & Yang, 2008a,b,c). In this paper, the title new zinc(II) complex, Fig. 1, is reported.

In the title complex, the ZnII atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two iodide ions in a tetrahedral coordination. The coordinate bond lengths (Table 1) are typical and comparable to the corresponding values observed in the Schiff base zinc complexes we reported previously and other similar Schiff base zinc complexes (Zhu et al., 2007; Wei et al., 2007; Qiu, 2006a,b).

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds, forming chains running along the b axis (Table 2, Fig. 2).

Related literature top

For background to the chemistry of Schiff base complexes, see: Ali et al. (2008); Biswas et al. (2008); Chen et al. (2008); Darensbourg & Frantz (2007); Habibi et al. (2007); Kawamoto et al. (2008); Lipscomb & Sträter (1996); Tomat et al. (2007); Wu et al. (2008); Yuan et al. (2007). For related structures, see: Zhu (2008); Zhu & Yang (2008a,b,c); Qiu (2006a,b); Wei et al. (2007); Zhu et al. (2007).

Experimental top

The Schiff base compound was prepared by the condensation of equimolar amounts of 5-bromosalicylaldehyde with 2-piperidin-1-ylethylamine in a methanol solution. The complex was prepared by the following method. To an anhydrous methanol solution (5 ml) of ZnI2 (31.9 mg, 0.1 mmol) was added a methanol solution (10 ml) of the Schiff base compound (31.1 mg, 0.1 mmol) with stirring. The mixture was stirred for 30 min at room temperature and filtered. Upon keeping the filtrate in air for a few days, colorless block-shaped crystals were formed.

Refinement top

H2 was located from a difference Fourier map and refined isotropically, with N—H distance restrained to 0.90 (1) Å. Other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, with ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title complex.
{4-Bromo-2-[2-(piperidin-1-ium-1-yl)ethyliminomethyl]phenolato}diiodidozinc(II) top
Crystal data top
[ZnI2(C14H19BrN2O)]F(000) = 1184
Mr = 630.39Dx = 2.149 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2365 reflections
a = 10.470 (3) Åθ = 2.5–25.1°
b = 12.351 (3) ŵ = 6.48 mm1
c = 15.426 (4) ÅT = 298 K
β = 102.326 (3)°Block, colorless
V = 1948.8 (9) Å30.17 × 0.15 × 0.15 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
4193 independent reflections
Radiation source: fine-focus sealed tube2953 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1312
Tmin = 0.406, Tmax = 0.443k = 1515
14478 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0326P)2 + 0.0119P]
where P = (Fo2 + 2Fc2)/3
4193 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 0.68 e Å3
1 restraintΔρmin = 1.09 e Å3
Crystal data top
[ZnI2(C14H19BrN2O)]V = 1948.8 (9) Å3
Mr = 630.39Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.470 (3) ŵ = 6.48 mm1
b = 12.351 (3) ÅT = 298 K
c = 15.426 (4) Å0.17 × 0.15 × 0.15 mm
β = 102.326 (3)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
4193 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
2953 reflections with I > 2σ(I)
Tmin = 0.406, Tmax = 0.443Rint = 0.053
14478 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.68 e Å3
4193 reflectionsΔρmin = 1.09 e Å3
193 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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
xyzUiso*/Ueq
Zn10.16997 (7)0.57708 (5)0.70705 (4)0.03725 (18)
I10.02704 (5)0.68332 (4)0.61843 (3)0.05599 (16)
I20.16625 (5)0.53139 (4)0.86722 (3)0.05989 (16)
Br10.46329 (7)0.66143 (6)0.32863 (4)0.04966 (19)
O10.3336 (4)0.6472 (3)0.6911 (2)0.0409 (10)
N10.2025 (4)0.4456 (3)0.6339 (3)0.0316 (10)
N20.0218 (5)0.2189 (4)0.6686 (3)0.0329 (10)
C10.3224 (5)0.5601 (4)0.5493 (3)0.0331 (13)
C20.3580 (6)0.6466 (4)0.6099 (3)0.0354 (13)
C30.4260 (6)0.7331 (5)0.5832 (4)0.0463 (16)
H30.44940.79090.62210.056*
C40.4595 (6)0.7367 (5)0.5032 (4)0.0464 (15)
H40.50630.79530.48830.056*
C50.4238 (6)0.6527 (5)0.4440 (3)0.0356 (14)
C60.3578 (6)0.5660 (4)0.4664 (3)0.0365 (14)
H60.33560.50950.42610.044*
C70.2634 (5)0.4608 (4)0.5703 (3)0.0321 (13)
H70.26970.40140.53430.039*
C80.1621 (6)0.3353 (4)0.6490 (4)0.0382 (14)
H8A0.21130.30960.70590.046*
H8B0.18140.28800.60320.046*
C90.0187 (6)0.3307 (4)0.6481 (4)0.0405 (14)
H9A0.00130.38110.69160.049*
H9B0.03050.35250.59010.049*
C100.1500 (6)0.2221 (5)0.6981 (4)0.0511 (17)
H10A0.21660.25350.65140.061*
H10B0.14110.26800.75010.061*
C110.1929 (7)0.1106 (6)0.7199 (5)0.0611 (19)
H11A0.13160.08300.77140.073*
H11B0.27800.11580.73520.073*
C120.2011 (7)0.0321 (6)0.6442 (5)0.068 (2)
H12A0.22000.04000.66300.082*
H12B0.27110.05330.59510.082*
C130.0735 (8)0.0318 (5)0.6150 (4)0.0585 (19)
H13A0.08040.01550.56410.070*
H13B0.00600.00300.66250.070*
C140.0340 (7)0.1429 (5)0.5910 (4)0.0466 (16)
H14A0.09890.17060.54140.056*
H14B0.04900.13880.57280.056*
H20.038 (5)0.197 (5)0.716 (3)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0429 (4)0.0396 (4)0.0303 (3)0.0049 (3)0.0101 (3)0.0033 (3)
I10.0597 (3)0.0710 (3)0.0357 (2)0.0164 (2)0.0068 (2)0.0024 (2)
I20.0858 (4)0.0614 (3)0.0341 (2)0.0066 (3)0.0165 (2)0.0058 (2)
Br10.0485 (4)0.0681 (5)0.0363 (3)0.0073 (3)0.0178 (3)0.0093 (3)
O10.046 (3)0.049 (2)0.0271 (19)0.013 (2)0.0072 (17)0.0100 (17)
N10.031 (3)0.028 (2)0.036 (2)0.003 (2)0.008 (2)0.0024 (19)
N20.034 (3)0.034 (3)0.030 (2)0.001 (2)0.008 (2)0.004 (2)
C10.030 (3)0.034 (3)0.032 (3)0.002 (3)0.000 (2)0.004 (2)
C20.036 (4)0.040 (3)0.029 (3)0.002 (3)0.004 (2)0.002 (2)
C30.062 (5)0.047 (4)0.029 (3)0.011 (3)0.009 (3)0.007 (3)
C40.049 (4)0.042 (4)0.050 (4)0.009 (3)0.015 (3)0.005 (3)
C50.037 (4)0.047 (4)0.025 (3)0.010 (3)0.012 (2)0.012 (2)
C60.043 (4)0.040 (3)0.026 (3)0.006 (3)0.006 (2)0.003 (2)
C70.037 (4)0.028 (3)0.030 (3)0.001 (2)0.004 (2)0.008 (2)
C80.038 (4)0.037 (3)0.039 (3)0.001 (3)0.007 (3)0.003 (3)
C90.040 (4)0.036 (3)0.045 (3)0.004 (3)0.009 (3)0.007 (3)
C100.040 (4)0.061 (4)0.054 (4)0.010 (3)0.015 (3)0.013 (3)
C110.047 (4)0.066 (5)0.075 (5)0.003 (4)0.022 (4)0.021 (4)
C120.061 (5)0.061 (5)0.078 (5)0.018 (4)0.006 (4)0.019 (4)
C130.075 (5)0.050 (4)0.053 (4)0.018 (4)0.017 (4)0.010 (3)
C140.053 (4)0.052 (4)0.036 (3)0.014 (3)0.014 (3)0.002 (3)
Geometric parameters (Å, º) top
Zn1—O11.981 (4)C6—H60.9300
Zn1—N12.047 (4)C7—H70.9300
Zn1—I22.5428 (9)C8—C91.500 (8)
Zn1—I12.5771 (9)C8—H8A0.9700
Br1—C51.914 (5)C8—H8B0.9700
O1—C21.329 (6)C9—H9A0.9700
N1—C71.293 (7)C9—H9B0.9700
N1—C81.460 (6)C10—C111.509 (9)
N2—C91.498 (7)C10—H10A0.9700
N2—C141.505 (7)C10—H10B0.9700
N2—C101.508 (7)C11—C121.507 (10)
N2—H20.90 (5)C11—H11A0.9700
C1—C61.407 (7)C11—H11B0.9700
C1—C21.417 (7)C12—C131.498 (10)
C1—C71.441 (7)C12—H12A0.9700
C2—C31.395 (8)C12—H12B0.9700
C3—C41.354 (8)C13—C141.502 (8)
C3—H30.9300C13—H13A0.9700
C4—C51.380 (8)C13—H13B0.9700
C4—H40.9300C14—H14A0.9700
C5—C61.359 (8)C14—H14B0.9700
O1—Zn1—N191.61 (16)N1—C8—H8B109.5
O1—Zn1—I2114.27 (10)C9—C8—H8B109.5
N1—Zn1—I2113.47 (12)H8A—C8—H8B108.0
O1—Zn1—I1109.08 (12)N2—C9—C8111.1 (4)
N1—Zn1—I1108.67 (12)N2—C9—H9A109.4
I2—Zn1—I1116.86 (3)C8—C9—H9A109.4
C2—O1—Zn1117.4 (3)N2—C9—H9B109.4
C7—N1—C8117.6 (4)C8—C9—H9B109.4
C7—N1—Zn1118.0 (3)H9A—C9—H9B108.0
C8—N1—Zn1124.4 (3)N2—C10—C11111.7 (5)
C9—N2—C14112.8 (4)N2—C10—H10A109.3
C9—N2—C10110.5 (4)C11—C10—H10A109.3
C14—N2—C10109.1 (5)N2—C10—H10B109.3
C9—N2—H2106 (5)C11—C10—H10B109.3
C14—N2—H2113 (4)H10A—C10—H10B107.9
C10—N2—H2106 (5)C12—C11—C10112.6 (6)
C6—C1—C2118.6 (5)C12—C11—H11A109.1
C6—C1—C7117.2 (5)C10—C11—H11A109.1
C2—C1—C7123.9 (5)C12—C11—H11B109.1
O1—C2—C3119.1 (5)C10—C11—H11B109.1
O1—C2—C1123.3 (5)H11A—C11—H11B107.8
C3—C2—C1117.5 (5)C13—C12—C11109.1 (6)
C4—C3—C2122.8 (6)C13—C12—H12A109.9
C4—C3—H3118.6C11—C12—H12A109.9
C2—C3—H3118.6C13—C12—H12B109.9
C3—C4—C5119.5 (6)C11—C12—H12B109.9
C3—C4—H4120.2H12A—C12—H12B108.3
C5—C4—H4120.2C12—C13—C14112.5 (6)
C6—C5—C4120.3 (5)C12—C13—H13A109.1
C6—C5—Br1120.2 (4)C14—C13—H13A109.1
C4—C5—Br1119.4 (4)C12—C13—H13B109.1
C5—C6—C1121.3 (5)C14—C13—H13B109.1
C5—C6—H6119.4H13A—C13—H13B107.8
C1—C6—H6119.4C13—C14—N2110.8 (5)
N1—C7—C1126.8 (5)C13—C14—H14A109.5
N1—C7—H7116.6N2—C14—H14A109.5
C1—C7—H7116.6C13—C14—H14B109.5
N1—C8—C9110.9 (4)N2—C14—H14B109.5
N1—C8—H8A109.5H14A—C14—H14B108.1
C9—C8—H8A109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.90 (5)1.85 (5)2.745 (6)176 (7)
Symmetry code: (i) x+1/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[ZnI2(C14H19BrN2O)]
Mr630.39
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)10.470 (3), 12.351 (3), 15.426 (4)
β (°) 102.326 (3)
V3)1948.8 (9)
Z4
Radiation typeMo Kα
µ (mm1)6.48
Crystal size (mm)0.17 × 0.15 × 0.15
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.406, 0.443
No. of measured, independent and
observed [I > 2σ(I)] reflections
14478, 4193, 2953
Rint0.053
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.093, 1.03
No. of reflections4193
No. of parameters193
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.68, 1.09

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Zn1—O11.981 (4)Zn1—I22.5428 (9)
Zn1—N12.047 (4)Zn1—I12.5771 (9)
O1—Zn1—N191.61 (16)O1—Zn1—I1109.08 (12)
O1—Zn1—I2114.27 (10)N1—Zn1—I1108.67 (12)
N1—Zn1—I2113.47 (12)I2—Zn1—I1116.86 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.90 (5)1.85 (5)2.745 (6)176 (7)
Symmetry code: (i) x+1/2, y1/2, z+3/2.
 

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Volume 65| Part 10| October 2009| Pages m1226-m1227
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