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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 64| Part 8| August 2008| Pages o1615-o1616

(E)-1,2-Bis(4-methyl­phen­yl)ethane-1,2-dione

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 23 July 2008; accepted 24 July 2008; online 31 July 2008)

In the mol­ecule of the title compound, C16H14O2, a substituted benzil, the dicarbonyl unit has an s-trans conformation. This conformation is substanti­ated by the O—C—C—O torsion angle of 108.16 (15)°. The dihedral angle between the two aromatic rings is 72.00 (6)°. In the crystal structure, neighbouring mol­ecules are linked together by weak inter­molecular C—H⋯O hydrogen bonds and weak inter­molecular C—H⋯π inter­actions. In addition, the crystal structure is further stabilized by inter­molecular ππ inter­actions with centroid–centroid distances in the range 3.6000 (8)–3.8341 (8) Å.

Related literature

For bond-length data, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For carbonyl–carbonyl interactions, see Allen et al. (1998[Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320-329.]). For related structures and applications, see, for example: Fun & Kia, (2008[Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, o1617.]); Kaftory & Rubin, (1983[Kaftory, M. & Rubin, M. B. (1983). J. Chem. Soc. Perkin Trans. 2, pp. 149-154.]); Frey et al. (1995[Frey, J., Faraggi, E., Rappoport, Z. & Kaftory, M. (1995). J. Chem. Soc. Perkin Trans. 2, pp. 1745-1748.]); Crowley et al. (1983[Crowley, J. I., Balanson, R. D. & Mayerle, J. J. (1983). J. Am. Chem. Soc. 105, 6416-6422.]); More et al. (1987[More, M., Odou, G. & Lefebvre, J. (1987). Acta Cryst. B43, 398-405.]); Brown et al. (1965[Brown, C. J. & Sadanaga, R. (1965). Acta Cryst. 18, 158-164.]); Gabe et al. (1981[Gabe, E. J., Le Page, Y., Lee, F. L. & Barclay, L. R. C. (1981). Acta Cryst. B37, 197-200.]); Kimura et al. (1979[Kimura, M., McCluney, R. E. & Watson, W. H. (1979). Acta Cryst. B35, 483-484.]); Stevens & Dubois (1962[Stevens, B. & Dubois, J. T. (1962). J. Chem. Soc. pp. 2813-2815.]); Shimizu & Bartlett, (1976[Shimizu, N. & Bartlett, P. D. (1976). J. Am. Chem. Soc. 98, 4193-4200.]); Rubin (1978[Rubin, M. B. (1978). Chem. Rev. 78, 1121-1164.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14O2

  • Mr = 238.27

  • Monoclinic, P 21 /n

  • a = 6.5658 (1) Å

  • b = 7.0916 (1) Å

  • c = 26.5958 (5) Å

  • β = 96.473 (1)°

  • V = 1230.46 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100.0 (1) K

  • 0.30 × 0.22 × 0.09 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.993

  • 15023 measured reflections

  • 3562 independent reflections

  • 2473 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.129

  • S = 1.04

  • 3562 reflections

  • 165 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Selected distances (Å)

Cg1 is the centroid of the C1–C6 benzene ring.

C7—C8 1.5350 (19)
O1⋯O2 3.1702 (15)
Cg1⋯Cg1i 3.6000 (8)
Cg1⋯Cg1ii 3.8341 (8)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z.

Table 2
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9–C14 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2A⋯O1iii 0.93 2.44 3.2573 (18) 146
C14—H14ACg2iv 0.93 2.94 3.6105 (15) 130
Symmetry codes: (iii) x, y-1, z; (iv) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

Investigation of the photophysical properties of the α-dicarbonyls has focused on the intramolecular carbonyl group electronic interaction as a function of their geometrical relationship. As in previous extensive studies of the photochemistry (Stevens & Dubois, 1962; Shimizu & Bartlett, 1976) of these compounds, biacetyl and benzil were the exclusive experimental vehicles for photophysical study. The structure of vicinal di- and polycarbonyl compounds have been of interest for many years (Rubin, 1978; Crowley et al., 1983; Kaftory et al., 1983; Frey et al., 1995; Kimura et al., 1979). Only a limited amount of data has been gathered from solid-state configurations such as in single crystals or as inclusion dopants in host crystals.

In the title compound (I) (Fig.1), bond lengths, bond angles, and torsion angles of the dicarbonyl unit deviate significantly from normal values (Allen et al., 1987) in order to minimize the repulsive interactions resulting from juxtaposition of dipolar carbonyl groups (Allen et al., 1987). The C7–C8 bond distance connecting the carbonyl units is longer than those in normally sp2sp2 single bonds, such as in butadiene. This is probably the result of decreasing the unfavourable vicinal dipole-dipole interactions. The dicarbonyl unit has s-trans conformation as can be indicated by the torsion angles of O1–C7–C6–C1, and O2–C8–C9–C10 being 169.55 (13) and 179.45 (14)°, respectively. This conformation is substantiated by the torsion angle of O–C–C–O, being 108.16 (15)°. The overal effect is to maximize the distance between the two electronegative oxygen atoms [O1···O2 = 3.1702 (15) Å] and to allow orbital overlap of the dione with the π system of the benzene rings. The dihedral angle between two phenyl rings is 64.74 (5)°. In the crystal structure, neighbouring molecules are linked together by weak intermolecular C—H···O hydrogen bond and weak intermolecular C—H···π interaction. The packing mode (Fig. 2) tend to be dominated by van der Wwaals close packing considerations and the preference for aligning the substituted phenyl rings parallel to each other along the a axis at about 3.6000 (8) – 3.8341 (8) Å.

Related literature top

For bond-length data, see Allen et al. (1987, 1998). For related structures and applications, see, for example: Fun & Kia, (2008); Kaftory & Rubin, (1983); Frey et al. (1995); Crowley et al. (1983); More et al. (1987); Brown et al. (1965); Gabe et al. (1981); Kimura et al. (1979); Stevens & Dubois (1962); Shimizu & Bartlett, (1976); Rubin (1978).

Experimental top

The synthetic method has been described earlier (Frey et al., 1995). Single crystals suitable for X-ray diffraction were obtained by evaporation of an methanol solution at room temperature.

Refinement top

All of the hydrogen atoms were positioned geometrically and refined using a riding model with isotropic thermal parameters 1.2 or 1.5 times that of the parent atom.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with atom labels and 50% probability ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The crystal packing, showing parallel aligning of the benzene rings along the a-axis, and stacking of the molecules down the b-axis. Intermolecular interactions are shown as dashed lines.
(E)-1,2-Bis(4-methylphenyl)ethane-1,2-dione top
Crystal data top
C16H14O2F(000) = 504
Mr = 238.27Dx = 1.286 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2861 reflections
a = 6.5658 (1) Åθ = 3.0–29.0°
b = 7.0916 (1) ŵ = 0.08 mm1
c = 26.5958 (5) ÅT = 100 K
β = 96.473 (1)°Block, colourless
V = 1230.46 (3) Å30.30 × 0.22 × 0.09 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
3562 independent reflections
Radiation source: fine-focus sealed tube2473 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ϕ and ω scansθmax = 30.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 99
Tmin = 0.975, Tmax = 0.993k = 99
15023 measured reflectionsl = 3737
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0539P)2 + 0.2688P]
where P = (Fo2 + 2Fc2)/3
3562 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C16H14O2V = 1230.46 (3) Å3
Mr = 238.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.5658 (1) ŵ = 0.08 mm1
b = 7.0916 (1) ÅT = 100 K
c = 26.5958 (5) Å0.30 × 0.22 × 0.09 mm
β = 96.473 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
3562 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2473 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.993Rint = 0.046
15023 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.05Δρmax = 0.34 e Å3
3562 reflectionsΔρmin = 0.24 e Å3
165 parameters
Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
xyzUiso*/Ueq
O10.78303 (16)0.85817 (16)0.10574 (4)0.0265 (3)
O20.52337 (16)0.56364 (16)0.16163 (4)0.0284 (3)
C10.7563 (2)0.3603 (2)0.07576 (5)0.0216 (3)
H1A0.75850.31420.10860.026*
C20.7544 (2)0.2362 (2)0.03573 (5)0.0228 (3)
H2A0.75720.10710.04190.027*
C30.7484 (2)0.3022 (2)0.01380 (5)0.0211 (3)
C40.7468 (2)0.4963 (2)0.02211 (5)0.0206 (3)
H4A0.74220.54220.05500.025*
C50.7519 (2)0.6211 (2)0.01774 (5)0.0202 (3)
H5A0.75330.75020.01170.024*
C60.7550 (2)0.5541 (2)0.06734 (5)0.0193 (3)
C70.7559 (2)0.6884 (2)0.10961 (5)0.0200 (3)
C80.7002 (2)0.6162 (2)0.16073 (5)0.0210 (3)
C90.8525 (2)0.6278 (2)0.20558 (5)0.0197 (3)
C101.0524 (2)0.6905 (2)0.20242 (5)0.0216 (3)
H10A1.09340.72070.17100.026*
C111.1896 (2)0.7079 (2)0.24546 (5)0.0234 (3)
H11A1.32230.74950.24280.028*
C121.1314 (2)0.6638 (2)0.29296 (5)0.0233 (3)
C130.9340 (2)0.5956 (2)0.29583 (5)0.0237 (3)
H13A0.89490.56140.32710.028*
C140.7955 (2)0.5781 (2)0.25295 (5)0.0219 (3)
H14A0.66410.53310.25560.026*
C150.7434 (2)0.1652 (2)0.05715 (6)0.0273 (4)
H15A0.70750.23090.08850.041*
H15B0.64360.06900.05330.041*
H15C0.87610.10840.05730.041*
C161.2805 (3)0.6890 (3)0.33977 (6)0.0316 (4)
H16A1.21280.66290.36920.047*
H16B1.33020.81640.34130.047*
H16C1.39350.60380.33870.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0327 (6)0.0224 (6)0.0251 (5)0.0009 (5)0.0062 (4)0.0025 (5)
O20.0246 (5)0.0343 (7)0.0271 (6)0.0046 (5)0.0065 (4)0.0017 (5)
C10.0216 (7)0.0247 (8)0.0185 (6)0.0009 (6)0.0020 (5)0.0042 (6)
C20.0222 (7)0.0208 (8)0.0254 (7)0.0003 (6)0.0027 (6)0.0019 (6)
C30.0152 (6)0.0268 (8)0.0213 (7)0.0002 (6)0.0028 (5)0.0007 (6)
C40.0160 (6)0.0282 (8)0.0178 (6)0.0001 (6)0.0020 (5)0.0043 (6)
C50.0171 (6)0.0221 (8)0.0215 (7)0.0012 (6)0.0028 (5)0.0054 (6)
C60.0157 (6)0.0233 (8)0.0189 (6)0.0003 (6)0.0027 (5)0.0021 (6)
C70.0171 (6)0.0230 (8)0.0202 (7)0.0010 (6)0.0030 (5)0.0031 (6)
C80.0245 (7)0.0186 (8)0.0205 (6)0.0001 (6)0.0060 (6)0.0002 (6)
C90.0245 (7)0.0154 (7)0.0199 (6)0.0012 (6)0.0059 (5)0.0001 (6)
C100.0257 (7)0.0211 (8)0.0192 (6)0.0011 (6)0.0073 (6)0.0022 (6)
C110.0218 (7)0.0216 (8)0.0272 (7)0.0003 (6)0.0041 (6)0.0024 (6)
C120.0308 (8)0.0161 (7)0.0226 (7)0.0027 (6)0.0007 (6)0.0013 (6)
C130.0339 (8)0.0189 (8)0.0195 (7)0.0026 (7)0.0081 (6)0.0017 (6)
C140.0242 (7)0.0191 (8)0.0237 (7)0.0004 (6)0.0087 (6)0.0005 (6)
C150.0258 (8)0.0311 (9)0.0251 (7)0.0013 (7)0.0037 (6)0.0040 (7)
C160.0381 (9)0.0292 (9)0.0261 (8)0.0001 (8)0.0032 (7)0.0022 (7)
Geometric parameters (Å, º) top
O1—C71.2231 (18)C9—C141.3992 (18)
O2—C81.2221 (17)C10—C111.380 (2)
C1—C21.380 (2)C10—H10A0.9300
C1—C61.393 (2)C11—C121.3960 (19)
C1—H1A0.9300C11—H11A0.9300
C2—C31.394 (2)C12—C131.393 (2)
C2—H2A0.9300C12—C161.505 (2)
C3—C41.394 (2)C13—C141.382 (2)
C3—C151.505 (2)C13—H13A0.9300
C4—C51.378 (2)C14—H14A0.9300
C4—H4A0.9300C15—H15A0.9600
C5—C61.3999 (18)C15—H15B0.9600
C5—H5A0.9300C15—H15C0.9600
C6—C71.473 (2)C16—H16A0.9600
C7—C81.5350 (19)C16—H16B0.9600
C8—C91.470 (2)C16—H16C0.9600
C9—C101.398 (2)
O1···O23.1702 (15)Cg1···Cg1ii3.8341 (8)
Cg1···Cg1i3.6000 (8)
C2—C1—C6120.39 (13)C11—C10—C9120.56 (13)
C2—C1—H1A119.8C11—C10—H10A119.7
C6—C1—H1A119.8C9—C10—H10A119.7
C1—C2—C3120.77 (15)C10—C11—C12120.72 (14)
C1—C2—H2A119.6C10—C11—H11A119.6
C3—C2—H2A119.6C12—C11—H11A119.6
C4—C3—C2118.69 (13)C13—C12—C11118.59 (13)
C4—C3—C15121.12 (13)C13—C12—C16121.20 (13)
C2—C3—C15120.19 (14)C11—C12—C16120.21 (14)
C5—C4—C3120.87 (13)C14—C13—C12121.06 (13)
C5—C4—H4A119.6C14—C13—H13A119.5
C3—C4—H4A119.6C12—C13—H13A119.5
C4—C5—C6120.22 (14)C13—C14—C9120.15 (13)
C4—C5—H5A119.9C13—C14—H14A119.9
C6—C5—H5A119.9C9—C14—H14A119.9
C1—C6—C5119.05 (13)C3—C15—H15A109.5
C1—C6—C7121.06 (12)C3—C15—H15B109.5
C5—C6—C7119.89 (13)H15A—C15—H15B109.5
O1—C7—C6124.07 (12)C3—C15—H15C109.5
O1—C7—C8117.04 (13)H15A—C15—H15C109.5
C6—C7—C8118.65 (13)H15B—C15—H15C109.5
O2—C8—C9124.19 (12)C12—C16—H16A109.5
O2—C8—C7116.15 (12)C12—C16—H16B109.5
C9—C8—C7119.47 (12)H16A—C16—H16B109.5
C10—C9—C14118.86 (13)C12—C16—H16C109.5
C10—C9—C8121.78 (12)H16A—C16—H16C109.5
C14—C9—C8119.35 (13)H16B—C16—H16C109.5
C6—C1—C2—C30.9 (2)O1—C7—C8—C967.01 (18)
C1—C2—C3—C40.8 (2)C6—C7—C8—C9118.41 (15)
C1—C2—C3—C15179.15 (13)O2—C8—C9—C10179.46 (15)
C2—C3—C4—C50.3 (2)C7—C8—C9—C104.7 (2)
C15—C3—C4—C5179.83 (13)O2—C8—C9—C140.6 (2)
C3—C4—C5—C61.2 (2)C7—C8—C9—C14174.18 (13)
C2—C1—C6—C50.0 (2)C14—C9—C10—C111.8 (2)
C2—C1—C6—C7179.66 (13)C8—C9—C10—C11177.11 (14)
C4—C5—C6—C11.0 (2)C9—C10—C11—C120.1 (2)
C4—C5—C6—C7178.64 (12)C10—C11—C12—C132.2 (2)
C1—C6—C7—O1169.54 (14)C10—C11—C12—C16178.16 (14)
C5—C6—C7—O110.8 (2)C11—C12—C13—C142.3 (2)
C1—C6—C7—C816.28 (19)C16—C12—C13—C14178.02 (14)
C5—C6—C7—C8163.39 (12)C12—C13—C14—C90.4 (2)
O1—C7—C8—O2108.17 (16)C10—C9—C14—C131.6 (2)
C6—C7—C8—O266.42 (18)C8—C9—C14—C13177.28 (13)
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1iii0.932.443.2573 (18)146
C14—H14A···Cg2iv0.932.943.6105 (15)130
Symmetry codes: (iii) x, y1, z; (iv) x+3/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC16H14O2
Mr238.27
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)6.5658 (1), 7.0916 (1), 26.5958 (5)
β (°) 96.473 (1)
V3)1230.46 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.22 × 0.09
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.975, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
15023, 3562, 2473
Rint0.046
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.129, 1.05
No. of reflections3562
No. of parameters165
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected interatomic distances (Å) top
O1—C71.2231 (18)C7—C81.5350 (19)
O2—C81.2221 (17)
O1···O23.1702 (15)Cg1···Cg1ii3.8341 (8)
Cg1···Cg1i3.6000 (8)
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1iii0.93002.44003.2573 (18)146.00
C14—H14A···Cg2iv0.93002.94003.6105 (15)130.00
Symmetry codes: (iii) x, y1, z; (iv) x+3/2, y1/2, z+1/2.
 

Footnotes

Additional correspondance author, e-mail: zsrkk@yahoo.com.

Acknowledgements

HKF and RK thanks the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for the award of a post-doctoral research fellowship.

References

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Volume 64| Part 8| August 2008| Pages o1615-o1616
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