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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 8| August 2008| Page o1581
doi:10.1107/S1600536808022733

2-Methyl­phenyl 4-methyl­benzoate

B. Thimme Gowda,a* Sabine Foro,b K. S. Babithaa and Hartmut Fuessb

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 11 July 2008; accepted 19 July 2008; online 23 July 2008)

The conformation of the C=O bond in the title compound 2MP4MBA, C15H14O2, is anti to the ortho-methyl group in the phen­oxy ring. The bond parameters in 2MP4MBA are similar to those in 3-methyl­phenyl 4-methyl­benzoate (3MP4MBA), 4-methyl­phenyl 4-methyl­benzoate (4MP4MBA) and other aryl benzoates. The dihedral angle between the two aromatic rings in 2MP4MBA is 73.04 (8)°.

Related literature

For related literature, see Gowda et al. (2007[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007). Acta Cryst. E63, o3867.], 2008[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1390.]); Nayak & Gowda (2008[Nayak, R. & Gowda, B. T. (2008). Z. Naturforsch. Teil A, 63. In the press.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14O2

  • Mr = 226.26

  • Monoclinic, P 21 /c

  • a = 11.690 (2) Å

  • b = 9.670 (1) Å

  • c = 11.478 (2) Å

  • β = 104.50 (2)°

  • V = 1256.2 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 299 (2) K

  • 0.50 × 0.46 × 0.20 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.968, Tmax = 0.989

  • 7861 measured reflections

  • 2529 independent reflections

  • 1385 reflections with I > 2σ(I)

  • Rint = 0.021
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.200

  • S = 1.04

  • 2529 reflections

  • 181 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.15 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, 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: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022733/bx2161sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022733/bx2161Isup2.hkl

checkCIF report


Comment top

In the present work, as part of a study of the substituent effects on the crystal structures of aryl benzoates (Gowda et al., 2007; 2008), the structure of 2-methylphenyl 4-methylbenzoate (2MP4MBA) has been determined. The conformation of the C=O bond in 2MP4MBA is anti to the ortho-methyl group in the phenolic benzene ring (Fig. 1). The bond parameters in 2MP4MBA are similar to those in 3-methylphenyl 4-methylbenzoate (3MP4MBA), 4-methylphenyl 4-methylbenzoate (4MP4MBA) (Gowda et al., 2007) and other aryl benzoates (Gowda et al., 2008). The dihedral angle between the benzene and benzoyl rings in 2MP4MBA is 73.04 (8)°, compared to the values of 56.82 (7)° in 3MP4MBA and 63.57 (5)° in 4MP4MBA. The packing diagram of molecules in the crystal structure is shown in Fig. 2.

Related literature top

For related literature, see Gowda et al. (2007, 2008); Nayak & Gowda (2008).

Experimental top

The title compound was prepared according to a literature method (Nayak & Gowda, 2008). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2008). Single crystals of the title compound used for X-ray diffraction studies were obtained by slow evaporation of an ethanolic solution at room temperature.

Refinement top

The H atoms of the methyl groups were positioned with idealized geometry using a riding model with C—H = 0.96 Å. The other H atoms were located in difference map, and its positional parameters were refined freely [C—H = 0.87 (3)–1.05 (3) Å. All H atoms were refined with isotropic displacement parameters (Uiso(H) = 1.2 Ueq(CH) and 1.5Ueq(CH3))

To improve the values of R1, wR2, and GOOF, the bad three reflections (1 1 0 2 0 0 1 1 1) were omitted from the refinement.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Molecular packing of the title compound.
2-Methylphenyl 4-methylbenzoate top
Crystal data top
C15H14O2F(000) = 480
Mr = 226.26Dx = 1.196 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1609 reflections
a = 11.690 (2) Åθ = 2.8–27.9°
b = 9.670 (1) ŵ = 0.08 mm−1
c = 11.478 (2) ÅT = 299 K
β = 104.50 (2)°Prism, colourless
V = 1256.2 (3) Å30.50 × 0.46 × 0.20 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2529 independent reflections
Radiation source: fine-focus sealed tube1385 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Rotation method data acquisition using ω and ϕ scansθmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		h = −11→14
Tmin = 0.968, Tmax = 0.989k = −12→9
7861 measured reflectionsl = −13→14
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.200 w = 1/[σ2(Fo2) + (0.092P)2 + 0.342P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.006
2529 reflectionsΔρmax = 0.21 e Å−3
181 parametersΔρmin = −0.15 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.031 (6)
Crystal data top
C15H14O2V = 1256.2 (3) Å3
Mr = 226.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.690 (2) ŵ = 0.08 mm−1
b = 9.670 (1) ÅT = 299 K
c = 11.478 (2) Å0.50 × 0.46 × 0.20 mm
β = 104.50 (2)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2529 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		1385 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.989Rint = 0.021
7861 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.200H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.21 e Å−3
2529 reflectionsΔρmin = −0.15 e Å−3
181 parameters
Special details top

Experimental. empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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*/Ueq
C10.5348 (2)0.2164 (2)0.4626 (2)0.0639 (6)
C20.5493 (2)0.1082 (2)0.3892 (2)0.0665 (6)
C30.4583 (3)0.0849 (3)0.2881 (2)0.0818 (8)
H30.465 (2)0.002 (3)0.238 (3)0.098*
C40.3581 (3)0.1645 (4)0.2630 (3)0.0920 (9)
H40.293 (3)0.134 (3)0.192 (3)0.110*
C50.3464 (3)0.2706 (4)0.3381 (3)0.0929 (10)
H50.282 (3)0.329 (3)0.318 (3)0.111*
C60.4355 (3)0.2979 (3)0.4402 (3)0.0787 (8)
H60.436 (3)0.363 (3)0.493 (3)0.094*
C70.7074 (2)0.3305 (2)0.5779 (2)0.0642 (6)
C80.8038 (2)0.3150 (2)0.6887 (2)0.0623 (6)
C90.8060 (2)0.2066 (3)0.7680 (2)0.0713 (7)
H90.741 (2)0.137 (3)0.754 (2)0.086*
C100.8988 (2)0.1943 (3)0.8698 (2)0.0774 (7)
H100.901 (2)0.116 (3)0.926 (2)0.093*
C110.9911 (2)0.2878 (3)0.8946 (2)0.0786 (7)
C120.9879 (3)0.3953 (3)0.8146 (3)0.0899 (9)
H121.052 (3)0.462 (3)0.823 (3)0.108*
C130.8960 (2)0.4098 (3)0.7127 (3)0.0802 (7)
H130.896 (2)0.489 (3)0.650 (2)0.096*
C140.6588 (2)0.0208 (3)0.4190 (3)0.0866 (8)
H14A0.6673−0.02100.49650.129*
H14B0.72640.07770.42030.129*
H14C0.6527−0.05000.35920.129*
C151.0906 (3)0.2722 (4)1.0064 (3)0.1079 (11)
H15A1.15860.23440.98510.162*
H15B1.06650.21111.06180.162*
H15C1.11010.36101.04340.162*
O10.62322 (15)0.23295 (16)0.57090 (14)0.0759 (5)
O20.70209 (16)0.41780 (18)0.50210 (17)0.0858 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0637 (14)0.0663 (13)0.0593 (13)−0.0023 (11)0.0110 (11)0.0084 (10)
C20.0723 (15)0.0639 (13)0.0640 (14)0.0001 (11)0.0183 (12)0.0075 (11)
C30.097 (2)0.0791 (17)0.0654 (16)−0.0007 (15)0.0136 (14)0.0045 (13)
C40.089 (2)0.102 (2)0.0721 (17)−0.0112 (18)−0.0030 (15)0.0184 (17)
C50.0727 (19)0.101 (2)0.100 (2)0.0197 (16)0.0132 (17)0.0367 (19)
C60.0850 (19)0.0726 (15)0.0808 (18)0.0127 (14)0.0252 (15)0.0111 (13)
C70.0685 (15)0.0544 (12)0.0733 (15)0.0050 (11)0.0248 (12)−0.0033 (11)
C80.0629 (13)0.0598 (12)0.0673 (14)−0.0005 (10)0.0220 (11)−0.0064 (10)
C90.0678 (15)0.0668 (14)0.0770 (16)−0.0082 (12)0.0141 (13)−0.0005 (12)
C100.0683 (16)0.0829 (17)0.0773 (17)−0.0054 (13)0.0115 (13)0.0052 (13)
C110.0633 (15)0.0930 (18)0.0776 (17)−0.0054 (13)0.0140 (12)−0.0117 (14)
C120.0740 (18)0.0924 (19)0.101 (2)−0.0253 (15)0.0165 (16)−0.0105 (17)
C130.0813 (18)0.0707 (15)0.0899 (19)−0.0129 (13)0.0242 (15)0.0009 (13)
C140.0866 (19)0.0814 (17)0.0954 (19)0.0142 (14)0.0294 (15)0.0050 (14)
C150.0766 (19)0.138 (3)0.098 (2)−0.0173 (18)0.0013 (16)−0.0083 (19)
O10.0790 (11)0.0763 (11)0.0667 (11)−0.0141 (9)0.0075 (8)0.0060 (8)
O20.0901 (13)0.0725 (11)0.0936 (14)0.0013 (9)0.0205 (10)0.0188 (9)
Geometric parameters (Å, º) top
C1—C61.373 (3)C8—C131.390 (3)
C1—C21.381 (3)C9—C101.386 (4)
C1—O11.413 (3)C9—H91.00 (3)
C2—C31.383 (4)C10—C111.382 (4)
C2—C141.499 (3)C10—H100.99 (3)
C3—C41.371 (4)C11—C121.382 (4)
C3—H31.00 (3)C11—C151.508 (4)
C4—C51.369 (4)C12—C131.383 (4)
C4—H41.01 (3)C12—H120.97 (3)
C5—C61.384 (4)C13—H131.05 (3)
C5—H50.92 (3)C14—H14A0.9600
C6—H60.87 (3)C14—H14B0.9600
C7—O21.202 (3)C14—H14C0.9600
C7—O11.351 (3)C15—H15A0.9600
C7—C81.481 (3)C15—H15B0.9600
C8—C91.385 (3)C15—H15C0.9600
C6—C1—C2123.3 (2)C10—C9—H9118.6 (15)
C6—C1—O1119.9 (2)C11—C10—C9121.6 (3)
C2—C1—O1116.6 (2)C11—C10—H10118.4 (16)
C1—C2—C3116.7 (2)C9—C10—H10120.0 (16)
C1—C2—C14121.1 (2)C12—C11—C10117.7 (3)
C3—C2—C14122.2 (2)C12—C11—C15121.9 (3)
C4—C3—C2121.5 (3)C10—C11—C15120.4 (3)
C4—C3—H3121.1 (16)C11—C12—C13121.7 (3)
C2—C3—H3117.2 (16)C11—C12—H12122.7 (18)
C5—C4—C3120.2 (3)C13—C12—H12115.5 (18)
C5—C4—H4123.4 (18)C12—C13—C8120.0 (3)
C3—C4—H4116.1 (18)C12—C13—H13121.3 (15)
C4—C5—C6120.2 (3)C8—C13—H13118.6 (15)
C4—C5—H5120.5 (19)C2—C14—H14A109.5
C6—C5—H5119 (2)C2—C14—H14B109.5
C1—C6—C5118.1 (3)H14A—C14—H14B109.5
C1—C6—H6115.4 (19)C2—C14—H14C109.5
C5—C6—H6126.5 (19)H14A—C14—H14C109.5
O2—C7—O1122.9 (2)H14B—C14—H14C109.5
O2—C7—C8125.6 (2)C11—C15—H15A109.5
O1—C7—C8111.49 (19)C11—C15—H15B109.5
C9—C8—C13118.9 (2)H15A—C15—H15B109.5
C9—C8—C7121.8 (2)C11—C15—H15C109.5
C13—C8—C7119.3 (2)H15A—C15—H15C109.5
C8—C9—C10120.1 (2)H15B—C15—H15C109.5
C8—C9—H9121.4 (15)C7—O1—C1119.55 (17)
C6—C1—C2—C30.9 (4)C13—C8—C9—C100.4 (4)
O1—C1—C2—C3174.9 (2)C7—C8—C9—C10178.9 (2)
C6—C1—C2—C14−179.0 (2)C8—C9—C10—C11−0.4 (4)
O1—C1—C2—C14−4.9 (3)C9—C10—C11—C120.3 (4)
C1—C2—C3—C4−0.7 (4)C9—C10—C11—C15179.7 (3)
C14—C2—C3—C4179.1 (2)C10—C11—C12—C13−0.1 (4)
C2—C3—C4—C50.4 (4)C15—C11—C12—C13−179.5 (3)
C3—C4—C5—C6−0.3 (5)C11—C12—C13—C80.1 (4)
C2—C1—C6—C5−0.7 (4)C9—C8—C13—C12−0.2 (4)
O1—C1—C6—C5−174.6 (2)C7—C8—C13—C12−178.8 (2)
C4—C5—C6—C10.4 (4)O2—C7—O1—C110.7 (3)
O2—C7—C8—C9−176.4 (2)C8—C7—O1—C1−169.31 (18)
O1—C7—C8—C93.7 (3)C6—C1—O1—C7−85.0 (3)
O2—C7—C8—C132.2 (4)C2—C1—O1—C7100.8 (2)
O1—C7—C8—C13−177.7 (2)

Experimental details

Crystal data
Chemical formulaC15H14O2
Mr226.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)11.690 (2), 9.670 (1), 11.478 (2)
β (°) 104.50 (2)
V (Å3)1256.2 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.50 × 0.46 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.968, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		7861, 2529, 1385
Rint0.021
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.200, 1.04
No. of reflections2529
No. of parameters181
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.21, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

 

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

First citationGowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2007). Acta Cryst. E63, o3867.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1390.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNayak, R. & Gowda, B. T. (2008). Z. Naturforsch. Teil A, 63. In the press.  Google Scholar
 First citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, 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. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 8| August 2008| Page o1581
doi:10.1107/S1600536808022733
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