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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o926.
Published online 2010 March 27. doi:  10.1107/S1600536810010676
PMCID: PMC2983880

(Biphenyl-4-yl)(phen­yl)methanone

Abstract

In the title compound, C19H14O, the dihedral angle between the two aromatic rings of the biphenyl residue is 8.0 (3)° and the dihedral angle between the two rings connected by the carbonyl C atom is 51.74 (18)°. There are no short C—H(...)O contacts in the crystal structure.

Related literature

For applications of the title compound, see: Kucybala & Wrzyszczynski (2002 [triangle]); van der Velden et al. (1980 [triangle]).

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Object name is e-66-0o926-scheme1.jpg

Experimental

Crystal data

  • C19H14O
  • M r = 258.30
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o926-efi1.jpg
  • a = 6.1445 (4) Å
  • b = 7.4298 (7) Å
  • c = 29.014 (2) Å
  • V = 1324.56 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 173 K
  • 0.32 × 0.29 × 0.12 mm

Data collection

  • Stoe IPDS II two-circle diffractometer
  • 6073 measured reflections
  • 1265 independent reflections
  • 1193 reflections with I > 2σ(I)
  • R int = 0.071

Refinement

  • R[F 2 > 2σ(F 2)] = 0.077
  • wR(F 2) = 0.182
  • S = 1.13
  • 1265 reflections
  • 182 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010676/hb5370sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010676/hb5370Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors gratefully acknowledge a research grant from the Higher Education Commission of Pakistan under project No. 20-Miscel/R&D/00/3834.

supplementary crystallographic information

Comment

Various biphenyl derivatives are used in the synthesis of pharmaceuticals, antifungal agents like bifonazole, optical brightening agents, dyes and polychlorinated biphenyls (PCBs). PCBs are used as heat-transfer agents, as electric insulators and are environmental pollutants causing carcinogenesis. 4-Phenylbenzophenone (4-benzoylbiphenyl) is used in luminescence chemistry, spectrophotometric analysis, molecular chemistry, and as a stating material for organometallic-complexes. 4-Benzoylbiphenyl is the main photoproduct of the photodecomposition of photoinitiator N-[(4-benzoyl)benzene sulfonyl]benzenesulfonamide in an aqueous solution (Kucybala & Wrzyszczynski 2002). Phosphorescence and optically detected magnetic resonance (ODMR) experiments are reported for the lowest excited triplet state of 4-benzoylbiphenyl and related compounds. These compounds have been studied in single-crystal form and have a lowest m* triplet state (van der Velden et al., 1980).

In the title compound, C19H14O, the dihedral angle between the two aromatic rings of the biphenyl residue is 8.0 (3)° and the dihedral angle between the two rings connected by the carbonyl C atom is 51.74 (18)°. There are no short C—H···O contacts.

Experimental

Biphenyl (11 mmol) in chloroform (5 ml) was added slowly to a stirred mixture of anhydrous aluminum chloride (4.5 g) and benzoyl chloride (11.5 mmol) in dry chloroform (15 ml), in an ice bath and reaction mixture stirred for half hour. it was further stirred at room temperature for 3 h. Upon completion reaction mixture was diluted with water, extracted with dichloromethane and concentrated. Recrystallization from ethanol afforded (I) in 87% yield as colourless plates: Anal. calcd. for C19H14O: C, 88.34; H, 5.46%; found: C, 88.41; H, 5.61%.

Refinement

Due to the absence of anomalous scatterers, the 1201 Friedel pairs were merged before refinement. H atoms were found in a difference map, but they were refined with fixed individual isotropic displacement parameters [Uiso(H) = 1.2Ueq(C)] using a riding model, with C—H = 0.95 Å.

Figures

Fig. 1.
Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C19H14OF(000) = 544
Mr = 258.30Dx = 1.295 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 4666 reflections
a = 6.1445 (4) Åθ = 2.8–25.9°
b = 7.4298 (7) ŵ = 0.08 mm1
c = 29.014 (2) ÅT = 173 K
V = 1324.56 (18) Å3Plate, colourless
Z = 40.32 × 0.29 × 0.12 mm

Data collection

Stoe IPDS II two-circle diffractometer1193 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
graphiteθmax = 25.6°, θmin = 2.7°
ω scansh = −6→7
6073 measured reflectionsk = −9→8
1265 independent reflectionsl = −35→35

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.077H-atom parameters constrained
wR(F2) = 0.182w = 1/[σ2(Fo2) + (0.0331P)2 + 3.7315P] where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
1265 reflectionsΔρmax = 0.38 e Å3
182 parametersΔρmin = −0.41 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (5)

Special details

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)

xyzUiso*/Ueq
C10.9334 (9)0.2473 (12)0.5985 (3)0.0345 (14)
O11.1328 (7)0.2424 (10)0.5980 (2)0.0489 (14)
C110.8158 (12)0.2442 (9)0.6443 (2)0.0329 (18)
C120.6194 (12)0.3247 (12)0.6502 (3)0.045 (2)
H120.54630.37610.62450.055*
C130.5235 (12)0.3323 (11)0.6943 (2)0.0418 (19)
H130.38650.38900.69880.050*
C140.6325 (14)0.2562 (12)0.7305 (3)0.050 (2)
H140.57110.26430.76050.060*
C150.8288 (12)0.1680 (9)0.7250 (2)0.0351 (17)
H150.89910.11240.75050.042*
C160.9205 (12)0.1628 (11)0.6813 (2)0.0363 (18)
H161.05570.10330.67670.044*
C210.8136 (11)0.2548 (7)0.5540 (2)0.0265 (15)
C220.6040 (10)0.1827 (8)0.5471 (2)0.0243 (14)
H220.52540.13550.57260.029*
C230.5128 (11)0.1800 (10)0.5041 (2)0.0316 (16)
H230.37340.12660.50030.038*
C240.6188 (11)0.2540 (7)0.4649 (2)0.0222 (14)
C250.8263 (11)0.3235 (10)0.4727 (2)0.0344 (17)
H250.90290.37390.44740.041*
C260.9260 (11)0.3227 (11)0.5153 (2)0.0341 (17)
H261.06980.36780.51860.041*
C310.5192 (10)0.2543 (8)0.4186 (2)0.0285 (14)
C320.3245 (11)0.1634 (9)0.4098 (2)0.0330 (16)
H320.25180.10410.43440.040*
C330.2347 (12)0.1577 (9)0.3659 (3)0.0370 (16)
H330.10350.09310.36080.044*
C340.3348 (12)0.2456 (10)0.3295 (2)0.0380 (17)
H340.27260.24370.29950.046*
C350.5263 (12)0.3357 (11)0.3378 (2)0.0415 (19)
H350.59770.39540.31310.050*
C360.6174 (11)0.3412 (10)0.3814 (2)0.0360 (17)
H360.74920.40540.38610.043*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.022 (3)0.044 (4)0.037 (3)0.001 (3)−0.001 (4)−0.002 (3)
O10.023 (2)0.086 (4)0.037 (2)−0.007 (3)0.004 (3)−0.007 (2)
C110.026 (4)0.047 (5)0.026 (4)−0.006 (3)0.004 (3)−0.001 (3)
C120.026 (4)0.077 (6)0.033 (4)−0.006 (4)−0.006 (3)0.003 (4)
C130.032 (4)0.055 (5)0.038 (4)0.005 (4)0.003 (3)−0.006 (4)
C140.039 (5)0.074 (7)0.038 (5)−0.003 (4)0.005 (4)−0.006 (4)
C150.041 (4)0.031 (4)0.033 (4)−0.006 (3)−0.002 (3)−0.003 (3)
C160.025 (4)0.049 (5)0.034 (4)0.000 (3)−0.005 (3)−0.009 (4)
C210.023 (3)0.014 (3)0.042 (4)−0.003 (2)0.010 (3)−0.006 (3)
C220.025 (3)0.017 (3)0.031 (4)−0.003 (3)0.001 (3)−0.002 (3)
C230.023 (3)0.038 (4)0.034 (4)0.000 (3)0.004 (3)−0.004 (3)
C240.025 (3)0.018 (3)0.024 (3)0.005 (2)0.000 (3)−0.003 (3)
C250.025 (4)0.046 (4)0.032 (4)−0.008 (3)0.011 (3)0.001 (3)
C260.020 (3)0.047 (5)0.035 (4)−0.002 (3)0.001 (3)0.004 (3)
C310.022 (3)0.028 (3)0.035 (4)−0.003 (3)0.001 (3)−0.003 (3)
C320.036 (4)0.028 (3)0.034 (4)−0.009 (3)−0.001 (3)0.002 (3)
C330.035 (3)0.032 (4)0.044 (4)0.001 (3)−0.003 (3)−0.006 (3)
C340.038 (4)0.048 (5)0.028 (3)0.010 (3)−0.006 (3)−0.002 (3)
C350.034 (4)0.057 (5)0.033 (4)0.003 (4)0.004 (3)−0.001 (3)
C360.025 (3)0.053 (4)0.030 (3)−0.006 (3)0.000 (3)−0.003 (3)

Geometric parameters (Å, °)

C1—O11.226 (7)C23—C241.421 (9)
C1—C211.489 (10)C23—H230.9500
C1—C111.512 (10)C24—C251.393 (9)
C11—C121.357 (11)C24—C311.476 (9)
C11—C161.391 (11)C25—C261.380 (10)
C12—C131.412 (10)C25—H250.9500
C12—H120.9500C26—H260.9500
C13—C141.368 (11)C31—C321.398 (9)
C13—H130.9500C31—C361.395 (9)
C14—C151.382 (11)C32—C331.388 (10)
C14—H140.9500C32—H320.9500
C15—C161.388 (10)C33—C341.387 (10)
C15—H150.9500C33—H330.9500
C16—H160.9500C34—C351.375 (10)
C21—C221.409 (9)C34—H340.9500
C21—C261.410 (10)C35—C361.385 (9)
C22—C231.368 (9)C35—H350.9500
C22—H220.9500C36—H360.9500
O1—C1—C21119.0 (8)C24—C23—H23118.8
O1—C1—C11119.3 (8)C25—C24—C23115.7 (6)
C21—C1—C11121.8 (5)C25—C24—C31121.8 (6)
C12—C11—C16120.4 (7)C23—C24—C31122.5 (6)
C12—C11—C1121.9 (7)C26—C25—C24123.4 (6)
C16—C11—C1117.6 (7)C26—C25—H25118.3
C11—C12—C13120.2 (7)C24—C25—H25118.3
C11—C12—H12119.9C25—C26—C21119.8 (6)
C13—C12—H12119.9C25—C26—H26120.1
C14—C13—C12118.4 (7)C21—C26—H26120.1
C14—C13—H13120.8C32—C31—C36116.8 (6)
C12—C13—H13120.8C32—C31—C24121.5 (6)
C13—C14—C15122.3 (8)C36—C31—C24121.7 (5)
C13—C14—H14118.8C33—C32—C31121.6 (6)
C15—C14—H14118.8C33—C32—H32119.2
C14—C15—C16118.2 (8)C31—C32—H32119.2
C14—C15—H15120.9C34—C33—C32120.6 (7)
C16—C15—H15120.9C34—C33—H33119.7
C15—C16—C11120.4 (7)C32—C33—H33119.7
C15—C16—H16119.8C35—C34—C33118.4 (7)
C11—C16—H16119.8C35—C34—H34120.8
C22—C21—C26118.1 (7)C33—C34—H34120.8
C22—C21—C1124.1 (6)C34—C35—C36121.4 (7)
C26—C21—C1117.5 (6)C34—C35—H35119.3
C23—C22—C21120.6 (6)C36—C35—H35119.3
C23—C22—H22119.7C35—C36—C31121.3 (6)
C21—C22—H22119.7C35—C36—H36119.4
C22—C23—C24122.4 (6)C31—C36—H36119.4
C22—C23—H23118.8
O1—C1—C11—C12150.5 (9)C22—C23—C24—C252.5 (9)
C21—C1—C11—C12−29.9 (12)C22—C23—C24—C31−178.9 (6)
O1—C1—C11—C16−26.5 (13)C23—C24—C25—C26−0.2 (10)
C21—C1—C11—C16153.1 (7)C31—C24—C25—C26−178.9 (7)
C16—C11—C12—C132.3 (12)C24—C25—C26—C21−2.3 (11)
C1—C11—C12—C13−174.5 (8)C22—C21—C26—C252.5 (10)
C11—C12—C13—C14−0.4 (12)C1—C21—C26—C25176.5 (7)
C12—C13—C14—C15−2.0 (13)C25—C24—C31—C32171.3 (6)
C13—C14—C15—C162.3 (12)C23—C24—C31—C32−7.3 (9)
C14—C15—C16—C11−0.2 (11)C25—C24—C31—C36−7.0 (9)
C12—C11—C16—C15−2.1 (11)C23—C24—C31—C36174.4 (6)
C1—C11—C16—C15174.9 (7)C36—C31—C32—C330.9 (9)
O1—C1—C21—C22150.3 (8)C24—C31—C32—C33−177.5 (6)
C11—C1—C21—C22−29.3 (11)C31—C32—C33—C34−1.1 (11)
O1—C1—C21—C26−23.3 (12)C32—C33—C34—C351.0 (11)
C11—C1—C21—C26157.1 (7)C33—C34—C35—C36−0.7 (11)
C26—C21—C22—C23−0.3 (9)C34—C35—C36—C310.5 (12)
C1—C21—C22—C23−173.9 (7)C32—C31—C36—C35−0.6 (10)
C21—C22—C23—C24−2.2 (10)C24—C31—C36—C35177.8 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5370).

References

  • Kucybala, K. & Wrzyszczynski, A. (2002). J. Photochem. Photobiol. A, 153, 109–112.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stoe & Cie (2001). X-AREA Stoe & Cie, Darmstadt, Germany.
  • Velden, G. P. M. de van der, Boer, E. & Veeman, W. S. (1980). J. Phys. Chem.84, 2634–2641.

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