2-Bromo-p-terphen­yl

Moon, S.-H.; Yoon, H.; Kang, Y.

doi:10.1107/S1600536810007348

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o743

doi:10.1107/S1600536810007348

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2-Bromo-p-terphenyl

Suk-Hee Moon,^a Heesook Yoon ^b and Youngjin Kang ^b ^*

^aSubdivision of Food Science, Kyungnam College of Information and Technology, Busan 616-701, Republic of Korea, and ^bDivision of Science Education, Kangwon National University, Chuncheon 200-701, Republic of Korea
^*Correspondence e-mail: kangy@kangwon.ac.kr

(Received 12 February 2010; accepted 26 February 2010; online 3 March 2010)

In the title compound, C₁₈H₁₃Br, the dihedral angles between the mean planes of the central benzene ring and the mean planes of the outer phenyl and bromophenyl rings are 33.47 (8) and 66.35 (8)°, respectively. In the crystal, weak C—H⋯π and intermolecular Br⋯Br [3.5503 (15) Å] interactions contribute to the stabilization of the packing.

Related literature

For the synthesis, see: France et al. (1938 ); Tadashi et al. (1962 ). For the Suzuki coupling reaction, see: Miyaura & Suzuki (1995 ). For cross-coupling reactions of o-halogenated arenes, see: Ishikawa & Manabe (2007 ). For organic light-emitting diodes, see: Kim et al. (2008 ). For related structures, see: Jones et al. (2005 ); Liang (2008 ); MacNeil & Decken (1999 ); Politzer et al. (2007 ).

Experimental

Crystal data

C₁₈H₁₃Br
M_r = 309.19
Monoclinic, C 2/c
a = 27.039 (10) Å
b = 7.597 (3) Å
c = 18.907 (7) Å
β = 133.650 (5)°
V = 2810 (2) Å³
Z = 8
Mo Kα radiation
μ = 2.91 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.476, T_max = 0.594
13933 measured reflections
3503 independent reflections
2246 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.02
3503 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
C—H⋯π interactions (Å, °)

Cg2 and Cg3 are the centroids of the C7–C12 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg3ⁱ	0.93	2.84	3.778 (4)	148
C14—H14⋯Cg2ⁱⁱ	0.93	2.97	3.658 (5)	147
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536810007348/jj2023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810007348/jj2023Isup2.hkl

checkCIF report

Comment top

Palladium-catalyzed cross-coupling reactions of aryl halides with arylboronic acids, often referred as Suzuki coupling reactions, are versatile synthetic methods for the preparation of unsymmetrical biaryls. The Suzuki coupling reactions have been applied extensively in the synthesis of natural products, nucleoside analogues, and pharmaceuticals (Miyaura & Suzuki, 1995). Cross-coupling reactions of o-halogenated arenes are very useful synthetically, if the halogen atom is converted to other functional groups, such as carbazole, anthracene and fluorene (Ishikawa & Manabe, 2007). Anthracene based terphenyl derivatives are widely used as emitting and/or host materials in organic light-emitting diodes (OLEDs) (Kim et al., 2008). To be good host materials in OLEDs, the host must have larger energy gap between the HOMO (Highest Occupied Molecular Orbital) and the LUMO (Lowest Unoccupied Molecular orbital) than in a dopant, because energy transfer occurs from host to dopant.

The introduction of substituents at the ortho-position of biary and terphenyl groups is often used in the preparation of an efficient host with a wide band gap, because the substitients suppress effective π-conjugation throughout the whole molecule. Therefore, the structures of biaryl and terphenyl derivatives bearing a halogen atom at the ortho -position are attractive as good precursors to materials oriented chemists and physicists. The title compound, C₁₈H₁₃Br,(I), was synthesized by the Pd-catalyzed cross coupling of 4-biphenylboronic acid with 1-bromo-2-iodobenzene in the presence of base (Na₂CO₃).

The dihedral angles between the mean planes of the central phenyl ring (C7-C12) and the mean planes of the outer phenyl (C13-C18) and the brominated phenyl (C1-C6) rings, are 33.47 (8)° and 66.35 (8)°, respectively (Fig. 1). All bond lengths and bond angles are normal and comparable to those observed in similar structures (MacNeil & Decken, 1999; Jones et al., 2005).

Weak C–H···Cg π-ring interactions are observed [C2–H2···Cg3; H2···Cg3 = Å; C2–H2···Cg = 148°, C2···Cg3-H2 = 3.778 (4) Å; 1/2+x,1/2-y,1/2+z and C14–H14···Cg2; H14···Cg2 = 2.97 Å; C14–H14···Cg2 = 147°, C14···Cg2–H14 = 3.658 (5) Å; 1-x,y,1/2-z; where Cg2 and Cg3 are the centroids of C7—C12 and C13—C18, respectively] (Fig. 2). Weak Br1···Br1 interactions also exist (3.5503 (15) Å; Politzer et al., 2007; Liang, 2008) and along with C–H···Cg π-ring interactions contribute to the stabilization of crystal packing.

Related literature top

For the synthesis, see: France et al. (1938); Tadashi et al. (1962). For the Suzuki coupling reaction, see: Miyaura & Suzuki (1995). For cross-coupling reactions of o-halogenated arenes, see: Ishikawa & Manabe (2007). For organic light-emitting diodes, see: Kim et al. (2008). For related structures, see: Jones et al. (2005); Liang (2008); MacNeil & Decken (1999); Politzer et al. (2007).

Experimental top

A mixture of 4-biphenyboronicacid (0.1 mol), 1-bromo-2iodobenzene (0.1 mol), Na₂CO₃ (0.6 mol, 2M in H₂O), and Pd(PPh₃)₄ (5% mol) was refluxed for 12 h. After being cooled to room temperature, the reaction mixture was quenched by water. The aqueous layer was extracted with CH₂Cl₂, and the combined organic layers were sequentially washed with saturated aqueous NaCl (20 mL), dried with MgSO₄, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using CH₂Cl₂ and hexane to give the titled compound as a colorless solid. Analytical data (France, et al., 1938; Tadashi, et al., 1962). ¹H NMR (CDCl₃, 300 MHz): 7.65 (m, 5H), 7.51 (m, 4H), 7.40 (m, 3H), 7.21 (m, 1H); MS(EI, m/z): 309 [M⁺]. Slow evaporation of CH₂Cl₂ gave suitable single crystals for X-ray analysis.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Weak Br···Br and C—H···Cg π-ring interactions (dashed lines) in the title compound.

2-Bromo-p-terphenyl top

Crystal data top

C₁₈H₁₃Br	F(000) = 1248
M_r = 309.19	D_x = 1.462 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3654 reflections
a = 27.039 (10) Å	θ = 2.1–28.4°
b = 7.597 (3) Å	µ = 2.91 mm⁻¹
c = 18.907 (7) Å	T = 293 K
β = 133.650 (5)°	Block, colorless
V = 2810 (2) Å³	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3503 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −34→36
T_min = 0.476, T_max = 0.594	k = −9→10
13933 measured reflections	l = −25→25

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0341P)² + 2.6031P] where P = (F_o² + 2F_c²)/3
3503 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₁₈H₁₃Br	V = 2810 (2) Å³
M_r = 309.19	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.039 (10) Å	µ = 2.91 mm⁻¹
b = 7.597 (3) Å	T = 293 K
c = 18.907 (7) Å	0.30 × 0.25 × 0.20 mm
β = 133.650 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3503 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2246 reflections with I > 2σ(I)
T_min = 0.476, T_max = 0.594	R_int = 0.028
13933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.02	Δρ_max = 0.43 e Å⁻³
3503 reflections	Δρ_min = −0.65 e Å⁻³
172 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 > 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
Br1	0.721104 (15)	0.25216 (4)	0.56047 (2)	0.07170 (13)
C1	0.69010 (12)	0.4341 (3)	0.59063 (16)	0.0458 (5)
C2	0.73645 (13)	0.5631 (3)	0.65377 (18)	0.0565 (6)
H2	0.7807	0.5590	0.6797	0.068*
C3	0.71685 (15)	0.6982 (3)	0.67834 (19)	0.0613 (7)
H3	0.7478	0.7861	0.7210	0.074*
C4	0.65143 (16)	0.7030 (3)	0.6398 (2)	0.0616 (7)
H4	0.6384	0.7930	0.6575	0.074*
C5	0.60498 (13)	0.5756 (3)	0.57514 (18)	0.0552 (6)
H5	0.5606	0.5819	0.5489	0.066*
C6	0.62281 (11)	0.4369 (3)	0.54788 (15)	0.0434 (5)
C7	0.57071 (12)	0.3039 (3)	0.47552 (17)	0.0446 (5)
C8	0.51546 (12)	0.3516 (3)	0.37957 (17)	0.0519 (6)
H8	0.5104	0.4684	0.3609	0.062*
C9	0.46779 (12)	0.2289 (3)	0.31111 (18)	0.0522 (6)
H9	0.4310	0.2648	0.2472	0.063*
C10	0.47356 (11)	0.0529 (3)	0.33573 (16)	0.0441 (5)
C11	0.52859 (12)	0.0067 (3)	0.43275 (16)	0.0520 (6)
H11	0.5334	−0.1097	0.4519	0.062*
C12	0.57609 (13)	0.1291 (3)	0.50101 (17)	0.0524 (6)
H12	0.6124	0.0940	0.5653	0.063*
C13	0.42539 (11)	−0.0832 (3)	0.26121 (16)	0.0453 (5)
C14	0.39663 (13)	−0.0664 (4)	0.16585 (18)	0.0592 (6)
H14	0.4062	0.0328	0.1483	0.071*
C15	0.35413 (16)	−0.1948 (4)	0.0972 (2)	0.0730 (8)
H15	0.3359	−0.1824	0.0340	0.088*
C16	0.33855 (14)	−0.3410 (4)	0.1214 (2)	0.0703 (8)
H16	0.3098	−0.4273	0.0749	0.084*
C17	0.36580 (13)	−0.3588 (3)	0.2151 (2)	0.0598 (7)
H17	0.3550	−0.4569	0.2316	0.072*
C18	0.40904 (13)	−0.2318 (3)	0.28455 (19)	0.0519 (6)
H18	0.4275	−0.2457	0.3477	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0723 (2)	0.0729 (2)	0.0885 (2)	0.00301 (14)	0.0625 (2)	−0.01335 (15)
C1	0.0545 (14)	0.0446 (12)	0.0456 (13)	0.0024 (11)	0.0373 (12)	0.0014 (10)
C2	0.0533 (14)	0.0587 (15)	0.0542 (14)	−0.0045 (12)	0.0358 (13)	0.0008 (12)
C3	0.0735 (19)	0.0519 (14)	0.0538 (16)	−0.0128 (13)	0.0421 (15)	−0.0089 (12)
C4	0.085 (2)	0.0461 (14)	0.0686 (17)	0.0016 (13)	0.0585 (17)	−0.0044 (12)
C5	0.0604 (15)	0.0474 (14)	0.0635 (16)	0.0056 (12)	0.0449 (14)	0.0019 (12)
C6	0.0498 (13)	0.0417 (12)	0.0408 (12)	0.0028 (10)	0.0320 (11)	0.0049 (9)
C7	0.0478 (13)	0.0444 (12)	0.0457 (13)	0.0023 (10)	0.0338 (12)	0.0007 (10)
C8	0.0521 (14)	0.0397 (13)	0.0531 (15)	0.0063 (11)	0.0322 (13)	0.0065 (11)
C9	0.0461 (13)	0.0519 (15)	0.0438 (13)	0.0079 (11)	0.0254 (11)	0.0078 (11)
C10	0.0424 (12)	0.0472 (12)	0.0451 (12)	0.0016 (10)	0.0312 (11)	0.0007 (10)
C11	0.0570 (15)	0.0439 (13)	0.0462 (14)	0.0000 (11)	0.0323 (13)	0.0063 (11)
C12	0.0528 (14)	0.0498 (14)	0.0406 (12)	−0.0006 (11)	0.0270 (12)	0.0044 (11)
C13	0.0404 (12)	0.0480 (13)	0.0467 (13)	0.0030 (10)	0.0298 (11)	0.0010 (10)
C14	0.0581 (15)	0.0671 (17)	0.0520 (15)	−0.0102 (13)	0.0378 (13)	−0.0029 (13)
C15	0.0733 (19)	0.085 (2)	0.0504 (16)	−0.0171 (16)	0.0388 (16)	−0.0123 (15)
C16	0.0628 (18)	0.0634 (18)	0.0646 (19)	−0.0129 (14)	0.0363 (16)	−0.0165 (14)
C17	0.0541 (15)	0.0479 (14)	0.0654 (17)	−0.0005 (12)	0.0367 (14)	0.0014 (13)
C18	0.0493 (13)	0.0500 (14)	0.0504 (14)	0.0041 (11)	0.0322 (12)	0.0047 (11)

Geometric parameters (Å, º) top

Br1—C1	1.897 (2)	C9—H9	0.9300
C1—C2	1.375 (3)	C10—C11	1.391 (3)
C1—C6	1.391 (3)	C10—C13	1.489 (3)
C2—C3	1.375 (4)	C11—C12	1.376 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.372 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C18	1.390 (3)
C4—C5	1.374 (4)	C13—C14	1.391 (3)
C4—H4	0.9300	C14—C15	1.378 (4)
C5—C6	1.397 (3)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.374 (4)
C6—C7	1.489 (3)	C15—H15	0.9300
C7—C8	1.383 (3)	C16—C17	1.377 (4)
C7—C12	1.386 (3)	C16—H16	0.9300
C8—C9	1.379 (3)	C17—C18	1.380 (3)
C8—H8	0.9300	C17—H17	0.9300
C9—C10	1.389 (3)	C18—H18	0.9300

C2—C1—C6	122.4 (2)	C9—C10—C11	117.1 (2)
C2—C1—Br1	116.95 (18)	C9—C10—C13	121.9 (2)
C6—C1—Br1	120.61 (17)	C11—C10—C13	120.9 (2)
C3—C2—C1	119.5 (2)	C12—C11—C10	121.5 (2)
C3—C2—H2	120.2	C12—C11—H11	119.2
C1—C2—H2	120.2	C10—C11—H11	119.2
C4—C3—C2	119.8 (2)	C11—C12—C7	121.1 (2)
C4—C3—H3	120.1	C11—C12—H12	119.5
C2—C3—H3	120.1	C7—C12—H12	119.5
C3—C4—C5	120.4 (2)	C18—C13—C14	118.1 (2)
C3—C4—H4	119.8	C18—C13—C10	121.7 (2)
C5—C4—H4	119.8	C14—C13—C10	120.2 (2)
C4—C5—C6	121.5 (2)	C15—C14—C13	120.8 (3)
C4—C5—H5	119.2	C15—C14—H14	119.6
C6—C5—H5	119.2	C13—C14—H14	119.6
C1—C6—C5	116.3 (2)	C16—C15—C14	120.4 (3)
C1—C6—C7	123.5 (2)	C16—C15—H15	119.8
C5—C6—C7	120.2 (2)	C14—C15—H15	119.8
C8—C7—C12	117.8 (2)	C15—C16—C17	119.6 (3)
C8—C7—C6	120.5 (2)	C15—C16—H16	120.2
C12—C7—C6	121.7 (2)	C17—C16—H16	120.2
C9—C8—C7	121.2 (2)	C16—C17—C18	120.4 (3)
C9—C8—H8	119.4	C16—C17—H17	119.8
C7—C8—H8	119.4	C18—C17—H17	119.8
C8—C9—C10	121.3 (2)	C17—C18—C13	120.8 (2)
C8—C9—H9	119.3	C17—C18—H18	119.6
C10—C9—H9	119.3	C13—C18—H18	119.6

C6—C1—C2—C3	1.8 (4)	C8—C9—C10—C13	−175.5 (2)
Br1—C1—C2—C3	−179.94 (19)	C9—C10—C11—C12	−1.3 (3)
C1—C2—C3—C4	0.0 (4)	C13—C10—C11—C12	175.5 (2)
C2—C3—C4—C5	−1.4 (4)	C10—C11—C12—C7	0.2 (4)
C3—C4—C5—C6	1.0 (4)	C8—C7—C12—C11	1.0 (4)
C2—C1—C6—C5	−2.2 (3)	C6—C7—C12—C11	−178.2 (2)
Br1—C1—C6—C5	179.65 (16)	C9—C10—C13—C18	−149.7 (2)
C2—C1—C6—C7	176.8 (2)	C11—C10—C13—C18	33.6 (3)
Br1—C1—C6—C7	−1.4 (3)	C9—C10—C13—C14	31.9 (3)
C4—C5—C6—C1	0.8 (3)	C11—C10—C13—C14	−144.8 (2)
C4—C5—C6—C7	−178.2 (2)	C18—C13—C14—C15	−1.1 (4)
C1—C6—C7—C8	−113.1 (3)	C10—C13—C14—C15	177.4 (3)
C5—C6—C7—C8	65.9 (3)	C13—C14—C15—C16	1.0 (5)
C1—C6—C7—C12	66.1 (3)	C14—C15—C16—C17	−0.1 (5)
C5—C6—C7—C12	−115.0 (3)	C15—C16—C17—C18	−0.7 (4)
C12—C7—C8—C9	−0.9 (4)	C16—C17—C18—C13	0.6 (4)
C6—C7—C8—C9	178.2 (2)	C14—C13—C18—C17	0.3 (3)
C7—C8—C9—C10	−0.3 (4)	C10—C13—C18—C17	−178.2 (2)
C8—C9—C10—C11	1.4 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C7–C12 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg3ⁱ	0.93	2.84	3.778 (4)	148
C14—H14···Cg2ⁱⁱ	0.93	2.97	3.658 (5)	147

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃Br
M_r	309.19
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	27.039 (10), 7.597 (3), 18.907 (7)
β (°)	133.650 (5)
V (Å³)	2810 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.476, 0.594
No. of measured, independent and observed [I > 2σ(I)] reflections	13933, 3503, 2246
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.02
No. of reflections	3503
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.65

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C7–C12 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg3ⁱ	0.93	2.84	3.778 (4)	148
C14—H14···Cg2ⁱⁱ	0.93	2.97	3.658 (5)	147

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

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) and funded by the Ministry of Education, Science and Technology. (2009-0072468)

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