supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, o2620    [ doi:10.1107/S1600536809039361 ]

Phenyl 4-methylbenzoate

B. T. Gowda, M. Tokarcík, J. Kozísek, P. A. Suchetan and H. Fuess

Abstract top

The structure of the title compound, C14H12O2, resembles those of phenyl benzoate and 4-methylphenyl benzoate, with similar bond parameters. The two aromatic rings make a dihedral angle of 76.0 (1)°. The plane of the central -C(=O)-O- group is twisted by 9.4 (2)° out of the plane of the benzoyl ring, and by 83.3 (1)° out of the plane of the phenyl ring. The crystal structure exhibits weak parallel stacking of the benzoyl rings, with an interplanar distance of 3.65 Å and an offset of 1.84 Å. The methyl group shows orientational disorder.

Comment top

In the present work, as a part of the study of the substituent effects on the crystal structures of aryl benzoates (Gowda et al., 2007a, b; 2008), the structure of phenyl-4-methylbenzoate (I) has been determined. The structure of (I) (Fig. 1) is similar to those of phenyl benzoate (II) (Adams & Morsi, 1976), 4-methylphenyl benzoate (III) (Gowda et al., 2007b), 4-methylphenyl 2-methylbenzoate (IV) (Gowda et al., 2008), 4-methylphenyl 4-methylbenzoate (V) (Gowda et al., 2007a) and other aryl benzoates. The two benzene rings make a dihedral angle of 76.0 (1)°, compared to the values of 55.7° for (II), 60.17 (7)° (III), 73.04 (8)° (IV) and 63.57 (5)° (V). The plane of the central –C(=O)–O– group in (I) is twisted 9.4 (2)° out of the plane of the benzoyl ring, and 83.3 (1)° out of the plane of the phenyl ring. The crystal structure exhibits weak parallel stacking of benzoyl rings, with interplanar distance of 3.65 Å and offset 1.84 Å. In the crystal structure, there are no classical hydrogen bonds. The molecules in the structure are packed into chains as viewed in the ac plane (Fig. 2).

Related literature top

For preparation of the compound, see: Nayak & Gowda (2009). For background to our study of the effects of substituent on the crystal structures of aryl benzoates and for related structures, see: Gowda et al. (2007a,b, 2008). For phenyl

benzoate, see: Adams & Morsi (1976);

Experimental top

The title compound was prepared according to a literature method (Nayak & Gowda, 2009). The purity of the compound was checked by determination of its melting point. It was characterized by infrared and NMR spectra (Nayak & Gowda, 2009). Colorless single crystals of the title compound were obtained by slow evaporation of its ethanol solution.

Refinement top

All hydrogen atoms were placed in calculated positions with C–H distances 0.93 or 0.96 Å. The C14 methyl group shows orientational disorder in the hydrogen atom positions. The two sets of methyl hydrogen atoms were refined with equal occupancy. The Uiso(H) values were set at 1.2 Ueq(C-aromatic) or 1.5 Ueq(C-methyl).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction , 2009); data reduction: CrysAlis RED (Oxford Diffraction , 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Molecular packing of the title compound.
Phenyl 4-methylbenzoate top
Crystal data top
C14H12O2F(000) = 448
Mr = 212.24Dx = 1.237 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9248 reflections
a = 12.3440 (4) Åθ = 3.1–29.3°
b = 8.1332 (2) ŵ = 0.08 mm−1
c = 12.1545 (4) ÅT = 295 K
β = 110.911 (4)°Block, colourless
V = 1139.89 (6) Å30.52 × 0.46 × 0.32 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Ruby (Gemini Mo) detector		2138 independent reflections
graphite1468 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1Rint = 0.027
ω scansθmax = 25.6°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −15→15
Tmin = 0.96, Tmax = 0.98k = −9→9
20946 measured reflectionsl = −14→14
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0889P)2 + 0.0575P]
where P = (Fo2 + 2Fc2)/3
2138 reflections(Δ/σ)max = 0.001
146 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.15 e Å−3
Crystal data top
C14H12O2V = 1139.89 (6) Å3
Mr = 212.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.3440 (4) ŵ = 0.08 mm−1
b = 8.1332 (2) ÅT = 295 K
c = 12.1545 (4) Å0.52 × 0.46 × 0.32 mm
β = 110.911 (4)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Ruby (Gemini Mo) detector		2138 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1468 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.98Rint = 0.027
20946 measured reflectionsθmax = 25.6°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.145Δρmax = 0.23 e Å−3
S = 1.03Δρmin = −0.15 e Å−3
2138 reflectionsAbsolute structure: ?
146 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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*/UeqOcc. (<1)
C10.44050 (14)0.7055 (2)0.52718 (13)0.0649 (4)
C20.42337 (16)0.6054 (2)0.60914 (16)0.0826 (5)
H20.35090.5590.59550.099*
C30.51407 (17)0.5731 (2)0.71233 (15)0.0847 (6)
H30.5030.50450.76860.102*
C40.61978 (16)0.6415 (2)0.73202 (15)0.0809 (5)
H40.6810.62010.80190.097*
C50.63602 (14)0.7415 (2)0.64933 (16)0.0792 (5)
H50.70850.78820.66340.095*
C60.54637 (15)0.7745 (2)0.54505 (15)0.0737 (5)
H60.55770.84190.48830.088*
C70.26747 (13)0.84141 (18)0.41132 (13)0.0602 (4)
C80.17152 (12)0.83643 (17)0.29559 (12)0.0558 (4)
C90.17601 (13)0.74161 (18)0.20301 (13)0.0629 (4)
H90.24270.68220.21080.075*
C100.08196 (13)0.73479 (19)0.09922 (14)0.0660 (4)
H100.08680.67160.03740.079*
C11−0.01947 (13)0.81929 (18)0.08448 (13)0.0633 (4)
C12−0.02227 (14)0.9156 (2)0.17716 (15)0.0718 (5)
H12−0.08890.97540.16910.086*
C130.07132 (14)0.92496 (18)0.28101 (14)0.0679 (4)
H130.06740.99110.34190.082*
C14−0.12267 (15)0.8048 (2)−0.02748 (15)0.0835 (5)
H14A−0.16560.906−0.0420.125*0.5
H14B−0.17150.7167−0.02030.125*0.5
H14C−0.0970.7825−0.09180.125*0.5
H14D−0.19240.8088−0.00980.125*0.5
H14E−0.11920.7023−0.06520.125*0.5
H14F−0.12240.8941−0.07910.125*0.5
O10.35063 (10)0.72961 (15)0.41782 (10)0.0865 (4)
O20.27223 (9)0.92969 (13)0.49154 (9)0.0758 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0612 (9)0.0712 (10)0.0534 (8)0.0089 (8)0.0095 (7)−0.0108 (7)
C20.0734 (11)0.0913 (12)0.0790 (11)−0.0181 (9)0.0221 (9)−0.0136 (10)
C30.1043 (15)0.0767 (11)0.0670 (11)−0.0104 (10)0.0230 (10)0.0040 (8)
C40.0817 (12)0.0714 (10)0.0689 (11)0.0066 (9)0.0016 (9)−0.0025 (8)
C50.0599 (10)0.0815 (12)0.0842 (12)−0.0029 (8)0.0110 (9)−0.0022 (9)
C60.0729 (11)0.0763 (11)0.0705 (10)0.0036 (9)0.0238 (9)0.0047 (8)
C70.0624 (9)0.0576 (8)0.0608 (9)−0.0016 (7)0.0222 (7)−0.0014 (7)
C80.0562 (8)0.0526 (8)0.0581 (8)−0.0029 (6)0.0198 (7)0.0001 (6)
C90.0572 (9)0.0656 (9)0.0629 (9)0.0044 (7)0.0178 (7)−0.0038 (7)
C100.0642 (10)0.0704 (10)0.0597 (9)−0.0018 (8)0.0176 (8)−0.0059 (7)
C110.0589 (9)0.0602 (9)0.0651 (9)−0.0043 (7)0.0153 (7)0.0109 (7)
C120.0622 (10)0.0683 (10)0.0806 (11)0.0143 (8)0.0204 (8)0.0094 (8)
C130.0733 (10)0.0615 (9)0.0697 (10)0.0077 (8)0.0264 (8)−0.0012 (7)
C140.0669 (10)0.0899 (12)0.0778 (11)−0.0072 (9)0.0063 (9)0.0131 (9)
O10.0739 (8)0.1056 (9)0.0623 (7)0.0271 (7)0.0024 (6)−0.0195 (6)
O20.0821 (8)0.0734 (7)0.0660 (7)0.0022 (6)0.0193 (6)−0.0148 (5)
Geometric parameters (Å, °) top
C1—C21.361 (2)C8—C131.387 (2)
C1—C61.366 (2)C9—C101.377 (2)
C1—O11.4082 (18)C9—H90.93
C2—C31.376 (2)C10—C111.383 (2)
C2—H20.93C10—H100.93
C3—C41.359 (2)C11—C121.383 (2)
C3—H30.93C11—C141.500 (2)
C4—C51.362 (2)C12—C131.376 (2)
C4—H40.93C12—H120.93
C5—C61.379 (2)C13—H130.93
C5—H50.93C14—H14A0.96
C6—H60.93C14—H14B0.96
C7—O21.1954 (16)C14—H14C0.96
C7—O11.3524 (18)C14—H14D0.96
C7—C81.481 (2)C14—H14E0.96
C8—C91.381 (2)C14—H14F0.96
C2—C1—C6121.27 (15)C8—C9—H9119.9
C2—C1—O1119.90 (15)C9—C10—C11121.80 (14)
C6—C1—O1118.65 (15)C9—C10—H10119.1
C1—C2—C3119.54 (17)C11—C10—H10119.1
C1—C2—H2120.2C12—C11—C10117.44 (14)
C3—C2—H2120.2C12—C11—C14121.56 (15)
C4—C3—C2120.02 (17)C10—C11—C14121.00 (15)
C4—C3—H3120C13—C12—C11121.45 (15)
C2—C3—H3120C13—C12—H12119.3
C3—C4—C5119.96 (16)C11—C12—H12119.3
C3—C4—H4120C12—C13—C8120.48 (15)
C5—C4—H4120C12—C13—H13119.8
C4—C5—C6120.86 (17)C8—C13—H13119.8
C4—C5—H5119.6C11—C14—H14A109.5
C6—C5—H5119.6C11—C14—H14B109.5
C1—C6—C5118.34 (16)H14A—C14—H14B109.5
C1—C6—H6120.8C11—C14—H14C109.5
C5—C6—H6120.8H14A—C14—H14C109.5
O2—C7—O1122.75 (13)H14B—C14—H14C109.5
O2—C7—C8125.51 (14)C11—C14—H14D109.5
O1—C7—C8111.72 (12)C11—C14—H14E109.5
C9—C8—C13118.62 (14)H14D—C14—H14E109.5
C9—C8—C7122.54 (13)C11—C14—H14F109.5
C13—C8—C7118.79 (13)H14D—C14—H14F109.5
C10—C9—C8120.18 (14)H14E—C14—H14F109.5
C10—C9—H9119.9C7—O1—C1118.32 (11)
C6—C1—C2—C30.3 (3)C7—C8—C9—C10176.63 (14)
O1—C1—C2—C3175.36 (15)C8—C9—C10—C11−0.9 (2)
C1—C2—C3—C40.2 (3)C9—C10—C11—C121.8 (2)
C2—C3—C4—C5−0.3 (3)C9—C10—C11—C14−177.47 (14)
C3—C4—C5—C6−0.1 (3)C10—C11—C12—C13−1.2 (2)
C2—C1—C6—C5−0.7 (3)C14—C11—C12—C13178.09 (15)
O1—C1—C6—C5−175.82 (14)C11—C12—C13—C8−0.3 (2)
C4—C5—C6—C10.6 (3)C9—C8—C13—C121.3 (2)
O2—C7—C8—C9174.22 (14)C7—C8—C13—C12−176.12 (14)
O1—C7—C8—C9−7.1 (2)O2—C7—O1—C16.3 (2)
O2—C7—C8—C13−8.5 (2)C8—C7—O1—C1−172.34 (13)
O1—C7—C8—C13170.12 (13)C2—C1—O1—C782.15 (19)
C13—C8—C9—C10−0.6 (2)C6—C1—O1—C7−102.63 (18)
Acknowledgements top

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Interreg IIIA, for financial support in the purchase of the diffractometer.

references
References top

Adams, J. M. & Morsi, S. E. (1976). Acta Cryst. B32, 1345–1347.

Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007a). Acta Cryst. E63, o3867.

Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1581.

Gowda, B. T., Foro, S., Nayak, R. & Fuess, H. (2007b). Acta Cryst. E63, o3563.

Nayak, R. & Gowda, B. T. (2009). Z. Naturforsch. Teil A, 63. In preparation.

Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.