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

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ISSN: 2056-9890

Phenyl 4-methyl­benzoate

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 15 September 2009; accepted 28 September 2009; online 3 October 2009)

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.

Related literature

For preparation of the compound, see: Nayak & Gowda (2009[Nayak, R. & Gowda, B. T. (2009). Z. Naturforsch. Teil A, 63. In preparation.]). For background to our study of the effects of substituents on the crystal structures of aryl benzoates and for related structures, see: Gowda et al. (2007a[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007a). Acta Cryst. E63, o3867.],b[Gowda, B. T., Foro, S., Nayak, R. & Fuess, H. (2007b). Acta Cryst. E63, o3563.], 2008[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1581.]). For phen­yl benzoate, see: Adams & Morsi (1976[Adams, J. M. & Morsi, S. E. (1976). Acta Cryst. B32, 1345-1347.]);

[Scheme 1]

Experimental

Crystal data
  • C14H12O2

  • Mr = 212.24

  • Monoclinic, P 21 /c

  • a = 12.3440 (4) Å

  • b = 8.1332 (2) Å

  • c = 12.1545 (4) Å

  • β = 110.911 (4)°

  • V = 1139.89 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 295 K

  • 0.52 × 0.46 × 0.32 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.96, Tmax = 0.98

  • 20946 measured reflections

  • 2138 independent reflections

  • 1468 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.145

  • S = 1.03

  • 2138 reflections

  • 146 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction , 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2002[Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


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).

Structure description 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).

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);

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 m3
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 mm1
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
Graphite monochromator1468 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 = 1515
Tmin = 0.96, Tmax = 0.98k = 99
20946 measured reflectionsl = 1414
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 Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C14H12O2V = 1139.89 (6) Å3
Mr = 212.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.3440 (4) ŵ = 0.08 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.03Δρmax = 0.23 e Å3
2138 reflectionsΔρmin = 0.16 e Å3
146 parameters
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*
C110.01947 (13)0.81929 (18)0.08448 (13)0.0633 (4)
C120.02227 (14)0.9156 (2)0.17716 (15)0.0718 (5)
H120.08890.97540.16910.086*
C130.07132 (14)0.92496 (18)0.28101 (14)0.0679 (4)
H130.06740.99110.34190.082*
C140.12267 (15)0.8048 (2)0.02748 (15)0.0835 (5)
H14A0.16560.9060.0420.125*0.5
H14B0.17150.71670.02030.125*0.5
H14C0.0970.78250.09180.125*0.5
H14D0.19240.80880.00980.125*0.5
H14E0.11920.70230.06520.125*0.5
H14F0.12240.89410.07910.125*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, º) 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—C110.9 (2)
C1—C2—C3—C40.2 (3)C9—C10—C11—C121.8 (2)
C2—C3—C4—C50.3 (3)C9—C10—C11—C14177.47 (14)
C3—C4—C5—C60.1 (3)C10—C11—C12—C131.2 (2)
C2—C1—C6—C50.7 (3)C14—C11—C12—C13178.09 (15)
O1—C1—C6—C5175.82 (14)C11—C12—C13—C80.3 (2)
C4—C5—C6—C10.6 (3)C9—C8—C13—C121.3 (2)
O2—C7—C8—C9174.22 (14)C7—C8—C13—C12176.12 (14)
O1—C7—C8—C97.1 (2)O2—C7—O1—C16.3 (2)
O2—C7—C8—C138.5 (2)C8—C7—O1—C1172.34 (13)
O1—C7—C8—C13170.12 (13)C2—C1—O1—C782.15 (19)
C13—C8—C9—C100.6 (2)C6—C1—O1—C7102.63 (18)

Experimental details

Crystal data
Chemical formulaC14H12O2
Mr212.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)12.3440 (4), 8.1332 (2), 12.1545 (4)
β (°) 110.911 (4)
V3)1139.89 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.52 × 0.46 × 0.32
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Ruby (Gemini Mo) detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.96, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections
20946, 2138, 1468
Rint0.027
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.145, 1.03
No. of reflections2138
No. of parameters146
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction , 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

 

Acknowledgements

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

First citationAdams, J. M. & Morsi, S. E. (1976). Acta Cryst. B32, 1345–1347.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationBrandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
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First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
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First citationGowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1581.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S., Nayak, R. & Fuess, H. (2007b). Acta Cryst. E63, o3563.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNayak, R. & Gowda, B. T. (2009). Z. Naturforsch. Teil A, 63. In preparation.  Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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