(Biphenyl-4-yl)(phen­yl)methanone

Saeed, A.; Samra, S.A.; Irfan, M.; Bolte, M.

doi:10.1107/S1600536810010676

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o926

doi:10.1107/S1600536810010676

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(Biphenyl-4-yl)(phenyl)methanone

Aamer Saeed,^a ^* Shahid Ameen Samra,^a,^b Madiha Irfan ^a and Michael Bolte ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bKohat University of Science and Technology (KUST), Kohat, 26000, NWFP, Pakistan, and ^cInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 20 March 2010; accepted 22 March 2010; online 27 March 2010)

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 ); van der Velden et al. (1980 ).

Experimental

Crystal data

C₁₉H₁₄O
M_r = 258.30
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.077
wR(F²) = 0.182
S = 1.13
1265 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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%.

Computing details top

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

Figures top

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

(Biphenyl-4-yl)(phenyl)methanone top

Crystal data top

C₁₉H₁₄O	F(000) = 544
M_r = 258.30	D_x = 1.295 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4666 reflections
a = 6.1445 (4) Å	θ = 2.8–25.9°
b = 7.4298 (7) Å	µ = 0.08 mm⁻¹
c = 29.014 (2) Å	T = 173 K
V = 1324.56 (18) Å³	Plate, colourless
Z = 4	0.32 × 0.29 × 0.12 mm

Data collection top

Stoe IPDS II two-circle diffractometer	1193 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.071
Graphite monochromator	θ_max = 25.6°, θ_min = 2.7°
ω scans	h = −6→7
6073 measured reflections	k = −9→8
1265 independent reflections	l = −35→35

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.077	H-atom parameters constrained
wR(F²) = 0.182	w = 1/[σ²(F_o²) + (0.0331P)² + 3.7315P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
1265 reflections	Δρ_max = 0.38 e Å⁻³
182 parameters	Δρ_min = −0.41 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (5)

Crystal data top

C₁₉H₁₄O	V = 1324.56 (18) Å³
M_r = 258.30	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 6.1445 (4) Å	µ = 0.08 mm⁻¹
b = 7.4298 (7) Å	T = 173 K
c = 29.014 (2) Å	0.32 × 0.29 × 0.12 mm

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.077	1 restraint
wR(F²) = 0.182	H-atom parameters constrained
S = 1.13	Δρ_max = 0.38 e Å⁻³
1265 reflections	Δρ_min = −0.41 e Å⁻³
182 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
C1	0.9334 (9)	0.2473 (12)	0.5985 (3)	0.0345 (14)
O1	1.1328 (7)	0.2424 (10)	0.5980 (2)	0.0489 (14)
C11	0.8158 (12)	0.2442 (9)	0.6443 (2)	0.0329 (18)
C12	0.6194 (12)	0.3247 (12)	0.6502 (3)	0.045 (2)
H12	0.5463	0.3761	0.6245	0.055*
C13	0.5235 (12)	0.3323 (11)	0.6943 (2)	0.0418 (19)
H13	0.3865	0.3890	0.6988	0.050*
C14	0.6325 (14)	0.2562 (12)	0.7305 (3)	0.050 (2)
H14	0.5711	0.2643	0.7605	0.060*
C15	0.8288 (12)	0.1680 (9)	0.7250 (2)	0.0351 (17)
H15	0.8991	0.1124	0.7505	0.042*
C16	0.9205 (12)	0.1628 (11)	0.6813 (2)	0.0363 (18)
H16	1.0557	0.1033	0.6767	0.044*
C21	0.8136 (11)	0.2548 (7)	0.5540 (2)	0.0265 (15)
C22	0.6040 (10)	0.1827 (8)	0.5471 (2)	0.0243 (14)
H22	0.5254	0.1355	0.5726	0.029*
C23	0.5128 (11)	0.1800 (10)	0.5041 (2)	0.0316 (16)
H23	0.3734	0.1266	0.5003	0.038*
C24	0.6188 (11)	0.2540 (7)	0.4649 (2)	0.0222 (14)
C25	0.8263 (11)	0.3235 (10)	0.4727 (2)	0.0344 (17)
H25	0.9029	0.3739	0.4474	0.041*
C26	0.9260 (11)	0.3227 (11)	0.5153 (2)	0.0341 (17)
H26	1.0698	0.3678	0.5186	0.041*
C31	0.5192 (10)	0.2543 (8)	0.4186 (2)	0.0285 (14)
C32	0.3245 (11)	0.1634 (9)	0.4098 (2)	0.0330 (16)
H32	0.2518	0.1041	0.4344	0.040*
C33	0.2347 (12)	0.1577 (9)	0.3659 (3)	0.0370 (16)
H33	0.1035	0.0931	0.3608	0.044*
C34	0.3348 (12)	0.2456 (10)	0.3295 (2)	0.0380 (17)
H34	0.2726	0.2437	0.2995	0.046*
C35	0.5263 (12)	0.3357 (11)	0.3378 (2)	0.0415 (19)
H35	0.5977	0.3954	0.3131	0.050*
C36	0.6174 (11)	0.3412 (10)	0.3814 (2)	0.0360 (17)
H36	0.7492	0.4054	0.3861	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.022 (3)	0.044 (4)	0.037 (3)	0.001 (3)	−0.001 (4)	−0.002 (3)
O1	0.023 (2)	0.086 (4)	0.037 (2)	−0.007 (3)	0.004 (3)	−0.007 (2)
C11	0.026 (4)	0.047 (5)	0.026 (4)	−0.006 (3)	0.004 (3)	−0.001 (3)
C12	0.026 (4)	0.077 (6)	0.033 (4)	−0.006 (4)	−0.006 (3)	0.003 (4)
C13	0.032 (4)	0.055 (5)	0.038 (4)	0.005 (4)	0.003 (3)	−0.006 (4)
C14	0.039 (5)	0.074 (7)	0.038 (5)	−0.003 (4)	0.005 (4)	−0.006 (4)
C15	0.041 (4)	0.031 (4)	0.033 (4)	−0.006 (3)	−0.002 (3)	−0.003 (3)
C16	0.025 (4)	0.049 (5)	0.034 (4)	0.000 (3)	−0.005 (3)	−0.009 (4)
C21	0.023 (3)	0.014 (3)	0.042 (4)	−0.003 (2)	0.010 (3)	−0.006 (3)
C22	0.025 (3)	0.017 (3)	0.031 (4)	−0.003 (3)	0.001 (3)	−0.002 (3)
C23	0.023 (3)	0.038 (4)	0.034 (4)	0.000 (3)	0.004 (3)	−0.004 (3)
C24	0.025 (3)	0.018 (3)	0.024 (3)	0.005 (2)	0.000 (3)	−0.003 (3)
C25	0.025 (4)	0.046 (4)	0.032 (4)	−0.008 (3)	0.011 (3)	0.001 (3)
C26	0.020 (3)	0.047 (5)	0.035 (4)	−0.002 (3)	0.001 (3)	0.004 (3)
C31	0.022 (3)	0.028 (3)	0.035 (4)	−0.003 (3)	0.001 (3)	−0.003 (3)
C32	0.036 (4)	0.028 (3)	0.034 (4)	−0.009 (3)	−0.001 (3)	0.002 (3)
C33	0.035 (3)	0.032 (4)	0.044 (4)	0.001 (3)	−0.003 (3)	−0.006 (3)
C34	0.038 (4)	0.048 (5)	0.028 (3)	0.010 (3)	−0.006 (3)	−0.002 (3)
C35	0.034 (4)	0.057 (5)	0.033 (4)	0.003 (4)	0.004 (3)	−0.001 (3)
C36	0.025 (3)	0.053 (4)	0.030 (3)	−0.006 (3)	0.000 (3)	−0.003 (3)

Geometric parameters (Å, º) top

C1—O1	1.226 (7)	C23—C24	1.421 (9)
C1—C21	1.489 (10)	C23—H23	0.9500
C1—C11	1.512 (10)	C24—C25	1.393 (9)
C11—C12	1.357 (11)	C24—C31	1.476 (9)
C11—C16	1.391 (11)	C25—C26	1.380 (10)
C12—C13	1.412 (10)	C25—H25	0.9500
C12—H12	0.9500	C26—H26	0.9500
C13—C14	1.368 (11)	C31—C32	1.398 (9)
C13—H13	0.9500	C31—C36	1.395 (9)
C14—C15	1.382 (11)	C32—C33	1.388 (10)
C14—H14	0.9500	C32—H32	0.9500
C15—C16	1.388 (10)	C33—C34	1.387 (10)
C15—H15	0.9500	C33—H33	0.9500
C16—H16	0.9500	C34—C35	1.375 (10)
C21—C22	1.409 (9)	C34—H34	0.9500
C21—C26	1.410 (10)	C35—C36	1.385 (9)
C22—C23	1.368 (9)	C35—H35	0.9500
C22—H22	0.9500	C36—H36	0.9500

O1—C1—C21	119.0 (8)	C24—C23—H23	118.8
O1—C1—C11	119.3 (8)	C25—C24—C23	115.7 (6)
C21—C1—C11	121.8 (5)	C25—C24—C31	121.8 (6)
C12—C11—C16	120.4 (7)	C23—C24—C31	122.5 (6)
C12—C11—C1	121.9 (7)	C26—C25—C24	123.4 (6)
C16—C11—C1	117.6 (7)	C26—C25—H25	118.3
C11—C12—C13	120.2 (7)	C24—C25—H25	118.3
C11—C12—H12	119.9	C25—C26—C21	119.8 (6)
C13—C12—H12	119.9	C25—C26—H26	120.1
C14—C13—C12	118.4 (7)	C21—C26—H26	120.1
C14—C13—H13	120.8	C32—C31—C36	116.8 (6)
C12—C13—H13	120.8	C32—C31—C24	121.5 (6)
C13—C14—C15	122.3 (8)	C36—C31—C24	121.7 (5)
C13—C14—H14	118.8	C33—C32—C31	121.6 (6)
C15—C14—H14	118.8	C33—C32—H32	119.2
C14—C15—C16	118.2 (8)	C31—C32—H32	119.2
C14—C15—H15	120.9	C34—C33—C32	120.6 (7)
C16—C15—H15	120.9	C34—C33—H33	119.7
C15—C16—C11	120.4 (7)	C32—C33—H33	119.7
C15—C16—H16	119.8	C35—C34—C33	118.4 (7)
C11—C16—H16	119.8	C35—C34—H34	120.8
C22—C21—C26	118.1 (7)	C33—C34—H34	120.8
C22—C21—C1	124.1 (6)	C34—C35—C36	121.4 (7)
C26—C21—C1	117.5 (6)	C34—C35—H35	119.3
C23—C22—C21	120.6 (6)	C36—C35—H35	119.3
C23—C22—H22	119.7	C35—C36—C31	121.3 (6)
C21—C22—H22	119.7	C35—C36—H36	119.4
C22—C23—C24	122.4 (6)	C31—C36—H36	119.4
C22—C23—H23	118.8

O1—C1—C11—C12	150.5 (9)	C22—C23—C24—C25	2.5 (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—C16	153.1 (7)	C31—C24—C25—C26	−178.9 (7)
C16—C11—C12—C13	2.3 (12)	C24—C25—C26—C21	−2.3 (11)
C1—C11—C12—C13	−174.5 (8)	C22—C21—C26—C25	2.5 (10)
C11—C12—C13—C14	−0.4 (12)	C1—C21—C26—C25	176.5 (7)
C12—C13—C14—C15	−2.0 (13)	C25—C24—C31—C32	171.3 (6)
C13—C14—C15—C16	2.3 (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—C36	174.4 (6)
C1—C11—C16—C15	174.9 (7)	C36—C31—C32—C33	0.9 (9)
O1—C1—C21—C22	150.3 (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—C35	1.0 (11)
C11—C1—C21—C26	157.1 (7)	C33—C34—C35—C36	−0.7 (11)
C26—C21—C22—C23	−0.3 (9)	C34—C35—C36—C31	0.5 (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—C35	177.8 (6)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄O
M_r	258.30
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	173
a, b, c (Å)	6.1445 (4), 7.4298 (7), 29.014 (2)
V (Å³)	1324.56 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.29 × 0.12

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6073, 1265, 1193
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.182, 1.13
No. of reflections	1265
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.41

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Acknowledgements

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

References

Kucybala, K. & Wrzyszczynski, A. (2002). J. Photochem. Photobiol. A, 153, 109–112. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Velden, G. P. M. de van der, Boer, E. & Veeman, W. S. (1980). J. Phys. Chem. 84, 2634–2641. Google Scholar