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Acta Cryst. (2009). E65, o2599    [ doi:10.1107/S1600536809039397 ]

2,4-Dimethylphenyl 4-methylbenzoate

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

Abstract top

In the title compound, C16H16O2, the two aromatic rings form a dihedral angle of 49.1 (1)°. In the crystal structure, there are no classical hydrogen bonds. The long axes of the molecules are directed along the c axis.

Comment top

As part of studying the substituent effects on the crystal structures of aryl benzoates (Gowda, Foro et al., 2007; 2008; Gowda, Tokarčík et al., 2008; 2009), the structure of 2,4-dimethylphenyl 4-methylbenzoate (I) has been determined. The structure of (I) (Fig. 1) is similar to those of phenyl benzoate (II)(Adams & Morsi, 1976), phenyl 4-methylbenzoate (III) (Gowda, Tokarčík et al., 2009), 2-methylphenyl 4-methylbenzoate (IV) (Gowda, Foro et al., 2008), 4-methylphenyl 4-methylbenzoate (V) (Gowda, Foro et al., 2007) and 2,4-dimethylphenyl benzoate (VI) (Gowda, Tokarčík et al., 2008). The central –O—C=O group makes a dihedral angle of 6.1 (1)° with the benzoyl ring and 54.9 (1)° with the disubstituted phenyl ring. The two benzene rings make the dihedral angle of 49.1 (1)°, compared to the values of 55.7° for (II), 76.0 (1)° (III), 73.04 (8)° (IV), 63.57 (5)° (V) and 80.25 (5)° (VI). There are no classical hydrogen bonds in the crystal structure. The packing of molecules as viewed along the b axis is shown in Fig.2. The long axes of the molecules are directed along the c axis.

Related literature top

For the preparation of the compound, see: Nayak & Gowda (2009). For background to our study of the effect of substituents on the crystal structures of aryl benzoates and for related structures, see: Gowda, Foro et al. (2007, 2008); Gowda, Tokarčík et al. (2008, 2009). For phenyl benzoate, see: Adams & Morsi (1976);

Experimental top

The title compound was prepared according to the literature method (Nayak & Gowda, 2009). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2009). Colorless Single crystals of the title compound were obtained by slow evaporation of its ethanol solution. The X-ray diffraction studies were made at room temperature.

Refinement top

H atoms were placed in calculated positions and subsequently constrained to ride on their parent atoms, with C–H distances of 0.93 Å (C-aromatic) and 0.96 Å (C-methyl). The Uiso(H) values were set at 1.2 Ueq(C aromatic) and 1.5 Ueq(C methyl). The C15 methyl group exhibits orientational disorder of the H atoms, which were treated using the SHELX instruction AFIX 127.

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 as viewed along the b-axis.
2,4-Dimethylphenyl 4-methylbenzoate top
Crystal data top
C16H16O2F(000) = 512
Mr = 240.29Dx = 1.212 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8238 reflections
a = 11.8022 (3) Åθ = 2.6–29.1°
b = 7.4959 (2) ŵ = 0.08 mm−1
c = 15.6288 (4) ÅT = 295 K
β = 107.760 (3)°Block, colourless
V = 1316.75 (6) Å30.52 × 0.38 × 0.12 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur2
diffractometer with a Sapphire CCD detector		2497 independent reflections
graphite1917 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1Rint = 0.018
ω scansθmax = 25.7°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −14→14
Tmin = 0.96, Tmax = 0.991k = −9→9
15897 measured reflectionsl = −19→19
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)] = 0.042H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0673P)2 + 0.1263P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2497 reflectionsΔρmax = 0.15 e Å−3
167 parametersΔρmin = −0.14 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: 0.014 (2)
Crystal data top
C16H16O2V = 1316.75 (6) Å3
Mr = 240.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.8022 (3) ŵ = 0.08 mm−1
b = 7.4959 (2) ÅT = 295 K
c = 15.6288 (4) Å0.52 × 0.38 × 0.12 mm
β = 107.760 (3)°
Data collection top
Oxford Diffraction Xcalibur2
diffractometer with a Sapphire CCD detector		2497 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1917 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.991Rint = 0.018
15897 measured reflectionsθmax = 25.7°
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.126Δρmax = 0.15 e Å−3
S = 1.09Δρmin = −0.14 e Å−3
2497 reflectionsAbsolute structure: ?
167 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)
C10.40414 (14)0.71817 (19)−0.01638 (9)0.0553 (4)
C20.51327 (13)0.76241 (18)−0.02574 (9)0.0527 (4)
C30.51869 (13)0.7825 (2)−0.11255 (9)0.0579 (4)
H30.59130.8118−0.12070.069*
C40.42059 (14)0.7608 (2)−0.18776 (9)0.0604 (4)
C50.31413 (15)0.7133 (2)−0.17447 (10)0.0701 (5)
H50.24730.6958−0.2240.084*
C60.30490 (14)0.6913 (2)−0.08916 (10)0.0670 (4)
H60.23280.6589−0.0810.08*
C70.33024 (12)0.79735 (19)0.10460 (10)0.0550 (4)
C80.36066 (12)0.78320 (18)0.20315 (9)0.0515 (4)
C90.45901 (12)0.6895 (2)0.25536 (9)0.0563 (4)
H90.50790.62990.22810.068*
C100.48429 (13)0.6843 (2)0.34706 (9)0.0602 (4)
H100.55040.62080.3810.072*
C110.41410 (14)0.77096 (19)0.39020 (10)0.0593 (4)
C120.31643 (14)0.8645 (2)0.33777 (11)0.0669 (4)
H120.26770.92380.36530.08*
C130.28975 (13)0.8717 (2)0.24585 (10)0.0632 (4)
H130.22390.93610.21210.076*
C140.62123 (14)0.7885 (2)0.05441 (10)0.0680 (4)
H14A0.60630.88210.09150.102*
H14B0.68790.82030.03460.102*
H14C0.63840.67980.08840.102*
C150.43107 (18)0.7894 (3)−0.28053 (10)0.0820 (5)
H15A0.51340.8025−0.27670.123*0.5
H15B0.38840.8953−0.30620.123*0.5
H15C0.39810.6886−0.31770.123*0.5
H15D0.35320.7884−0.32370.123*0.5
H15E0.47820.6957−0.29420.123*0.5
H15F0.46850.9023−0.28270.123*0.5
C160.44110 (17)0.7610 (2)0.49069 (11)0.0781 (5)
H16A0.40140.65960.50590.117*
H16B0.41380.86790.5120.117*
H16C0.52540.74920.51830.117*
O10.40148 (9)0.69351 (15)0.07226 (6)0.0647 (3)
O20.25305 (10)0.88935 (17)0.05767 (7)0.0784 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0661 (9)0.0529 (8)0.0450 (8)0.0106 (7)0.0143 (6)0.0031 (6)
C20.0564 (8)0.0514 (8)0.0461 (8)0.0135 (6)0.0092 (6)0.0001 (6)
C30.0614 (9)0.0608 (9)0.0507 (8)0.0127 (7)0.0157 (7)0.0010 (6)
C40.0715 (10)0.0599 (9)0.0454 (8)0.0123 (7)0.0111 (7)−0.0027 (6)
C50.0696 (10)0.0784 (11)0.0503 (9)0.0004 (8)0.0004 (7)−0.0058 (7)
C60.0607 (9)0.0752 (11)0.0612 (10)−0.0030 (7)0.0125 (7)−0.0009 (8)
C70.0523 (8)0.0551 (9)0.0580 (8)0.0018 (6)0.0176 (6)0.0054 (6)
C80.0521 (7)0.0507 (8)0.0537 (8)−0.0020 (6)0.0191 (6)0.0046 (6)
C90.0560 (8)0.0596 (9)0.0561 (8)0.0043 (6)0.0215 (6)0.0064 (7)
C100.0592 (8)0.0648 (9)0.0568 (9)0.0011 (7)0.0179 (7)0.0098 (7)
C110.0710 (9)0.0559 (9)0.0548 (8)−0.0110 (7)0.0247 (7)0.0020 (7)
C120.0757 (10)0.0668 (10)0.0682 (10)0.0058 (8)0.0367 (8)0.0008 (8)
C130.0616 (8)0.0649 (10)0.0663 (9)0.0112 (7)0.0245 (7)0.0082 (7)
C140.0628 (9)0.0794 (11)0.0526 (9)0.0122 (8)0.0041 (7)0.0054 (7)
C150.0993 (13)0.0965 (14)0.0477 (9)0.0158 (10)0.0185 (9)0.0004 (8)
C160.1006 (13)0.0819 (12)0.0553 (9)−0.0093 (10)0.0287 (9)0.0016 (8)
O10.0757 (7)0.0698 (7)0.0500 (6)0.0191 (5)0.0213 (5)0.0094 (5)
O20.0729 (7)0.0965 (9)0.0624 (7)0.0288 (6)0.0154 (5)0.0131 (6)
Geometric parameters (Å, °) top
C1—C61.376 (2)C10—C111.380 (2)
C1—C21.380 (2)C10—H100.93
C1—O11.4075 (16)C11—C121.384 (2)
C2—C31.3858 (19)C11—C161.506 (2)
C2—C141.5023 (19)C12—C131.375 (2)
C3—C41.385 (2)C12—H120.93
C3—H30.93C13—H130.93
C4—C51.381 (2)C14—H14A0.96
C4—C151.508 (2)C14—H14B0.96
C5—C61.380 (2)C14—H14C0.96
C5—H50.93C15—H15A0.96
C6—H60.93C15—H15B0.96
C7—O21.1982 (16)C15—H15C0.96
C7—O11.3519 (17)C15—H15D0.96
C7—C81.475 (2)C15—H15E0.96
C8—C131.388 (2)C15—H15F0.96
C8—C91.3889 (19)C16—H16A0.96
C9—C101.373 (2)C16—H16B0.96
C9—H90.93C16—H16C0.96
C6—C1—C2122.28 (14)C12—C13—H13119.9
C6—C1—O1121.70 (14)C8—C13—H13119.9
C2—C1—O1115.94 (13)C2—C14—H14A109.5
C1—C2—C3116.94 (13)C2—C14—H14B109.5
C1—C2—C14121.63 (13)H14A—C14—H14B109.5
C3—C2—C14121.43 (14)C2—C14—H14C109.5
C4—C3—C2122.82 (15)H14A—C14—H14C109.5
C4—C3—H3118.6H14B—C14—H14C109.5
C2—C3—H3118.6C4—C15—H15A109.5
C5—C4—C3117.76 (14)C4—C15—H15B109.5
C5—C4—C15121.77 (14)H15A—C15—H15B109.5
C3—C4—C15120.46 (15)C4—C15—H15C109.5
C6—C5—C4121.29 (14)H15A—C15—H15C109.5
C6—C5—H5119.4H15B—C15—H15C109.5
C4—C5—H5119.4C4—C15—H15D109.5
C1—C6—C5118.88 (15)H15A—C15—H15D141.1
C1—C6—H6120.6H15B—C15—H15D56.3
C5—C6—H6120.6H15C—C15—H15D56.3
O2—C7—O1123.10 (13)C4—C15—H15E109.5
O2—C7—C8125.31 (13)H15A—C15—H15E56.3
O1—C7—C8111.59 (12)H15B—C15—H15E141.1
C13—C8—C9118.54 (13)H15C—C15—H15E56.3
C13—C8—C7118.51 (13)H15D—C15—H15E109.5
C9—C8—C7122.93 (13)C4—C15—H15F109.5
C10—C9—C8120.28 (14)H15A—C15—H15F56.3
C10—C9—H9119.9H15B—C15—H15F56.3
C8—C9—H9119.9H15C—C15—H15F141.1
C9—C10—C11121.70 (14)H15D—C15—H15F109.5
C9—C10—H10119.1H15E—C15—H15F109.5
C11—C10—H10119.1C11—C16—H16A109.5
C10—C11—C12117.70 (14)C11—C16—H16B109.5
C10—C11—C16121.25 (15)H16A—C16—H16B109.5
C12—C11—C16121.04 (14)C11—C16—H16C109.5
C13—C12—C11121.51 (14)H16A—C16—H16C109.5
C13—C12—H12119.2H16B—C16—H16C109.5
C11—C12—H12119.2C7—O1—C1119.70 (11)
C12—C13—C8120.27 (14)
C6—C1—C2—C31.2 (2)O1—C7—C8—C96.60 (19)
O1—C1—C2—C3178.26 (12)C13—C8—C9—C100.4 (2)
C6—C1—C2—C14−179.04 (14)C7—C8—C9—C10178.54 (13)
O1—C1—C2—C14−2.0 (2)C8—C9—C10—C11−0.1 (2)
C1—C2—C3—C40.3 (2)C9—C10—C11—C12−0.1 (2)
C14—C2—C3—C4−179.44 (14)C9—C10—C11—C16178.61 (14)
C2—C3—C4—C5−1.5 (2)C10—C11—C12—C13−0.1 (2)
C2—C3—C4—C15178.28 (14)C16—C11—C12—C13−178.80 (15)
C3—C4—C5—C61.2 (2)C11—C12—C13—C80.4 (2)
C15—C4—C5—C6−178.55 (15)C9—C8—C13—C12−0.6 (2)
C2—C1—C6—C5−1.5 (2)C7—C8—C13—C12−178.81 (14)
O1—C1—C6—C5−178.35 (14)O2—C7—O1—C113.5 (2)
C4—C5—C6—C10.2 (3)C8—C7—O1—C1−166.00 (12)
O2—C7—C8—C135.2 (2)C6—C1—O1—C7−62.88 (19)
O1—C7—C8—C13−175.27 (13)C2—C1—O1—C7120.07 (15)
O2—C7—C8—C9−172.89 (15)
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 purchasing 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. (2007). Acta Cryst. E63, o3867.

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

Gowda, B. T., Tokarčík, M., Kožíšek, J., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1280.

Gowda, B. T., Tokarčík, M., Kožíšek, J., Babitha, K. S. & Fuess, H. (2009). Acta Cryst. E65, oxxxx. [OM2279]

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

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

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

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