2,4-Dimethyl­phenyl 4-methyl­benzoate

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Suchetan, P.A.; Fuess, H.

doi:10.1107/S1600536809039397

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2599

https://doi.org/10.1107/S1600536809039397

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2,4-Dimethylphenyl 4-methylbenzoate

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b P. A. Suchetan ^a and Hartmut Fuess ^c

^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 25 September 2009; accepted 28 September 2009; online 3 October 2009)

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.

Related literature

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

Crystal data

C₁₆H₁₆O₂
M_r = 240.29
Monoclinic, P 2₁ /n
a = 11.8022 (3) Å
b = 7.4959 (2) Å
c = 15.6288 (4) Å
β = 107.760 (3)°
V = 1316.75 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.52 × 0.38 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.96, T_max = 0.991
15897 measured reflections
2497 independent reflections
1917 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.126
S = 1.09
2497 reflections
167 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 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 ); 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, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809039397/bt5076sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039397/bt5076Isup2.hkl

checkCIF report

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.

Structure description 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);

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

	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.
	Fig. 2. Molecular packing of the title compound as viewed along the b-axis.

2,4-Dimethylphenyl 4-methylbenzoate top

Crystal data top

C₁₆H₁₆O₂	F(000) = 512
M_r = 240.29	D_x = 1.212 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8238 reflections
a = 11.8022 (3) Å	θ = 2.6–29.1°
b = 7.4959 (2) Å	µ = 0.08 mm⁻¹
c = 15.6288 (4) Å	T = 295 K
β = 107.760 (3)°	Block, colourless
V = 1316.75 (6) Å³	0.52 × 0.38 × 0.12 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur2 diffractometer with a Sapphire CCD detector	2497 independent reflections
Graphite monochromator	1917 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.018
ω scans	θ_max = 25.7°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→14
T_min = 0.96, T_max = 0.991	k = −9→9
15897 measured reflections	l = −19→19

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0673P)² + 0.1263P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2497 reflections	Δρ_max = 0.15 e Å⁻³
167 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)

Crystal data top

C₁₆H₁₆O₂	V = 1316.75 (6) Å³
M_r = 240.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8022 (3) Å	µ = 0.08 mm⁻¹
b = 7.4959 (2) Å	T = 295 K
c = 15.6288 (4) Å	0.52 × 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)
T_min = 0.96, T_max = 0.991	R_int = 0.018
15897 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.09	Δρ_max = 0.15 e Å⁻³
2497 reflections	Δρ_min = −0.14 e Å⁻³
167 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.40414 (14)	0.71817 (19)	−0.01638 (9)	0.0553 (4)
C2	0.51327 (13)	0.76241 (18)	−0.02574 (9)	0.0527 (4)
C3	0.51869 (13)	0.7825 (2)	−0.11255 (9)	0.0579 (4)
H3	0.5913	0.8118	−0.1207	0.069*
C4	0.42059 (14)	0.7608 (2)	−0.18776 (9)	0.0604 (4)
C5	0.31413 (15)	0.7133 (2)	−0.17447 (10)	0.0701 (5)
H5	0.2473	0.6958	−0.224	0.084*
C6	0.30490 (14)	0.6913 (2)	−0.08916 (10)	0.0670 (4)
H6	0.2328	0.6589	−0.081	0.08*
C7	0.33024 (12)	0.79735 (19)	0.10460 (10)	0.0550 (4)
C8	0.36066 (12)	0.78320 (18)	0.20315 (9)	0.0515 (4)
C9	0.45901 (12)	0.6895 (2)	0.25536 (9)	0.0563 (4)
H9	0.5079	0.6299	0.2281	0.068*
C10	0.48429 (13)	0.6843 (2)	0.34706 (9)	0.0602 (4)
H10	0.5504	0.6208	0.381	0.072*
C11	0.41410 (14)	0.77096 (19)	0.39020 (10)	0.0593 (4)
C12	0.31643 (14)	0.8645 (2)	0.33777 (11)	0.0669 (4)
H12	0.2677	0.9238	0.3653	0.08*
C13	0.28975 (13)	0.8717 (2)	0.24585 (10)	0.0632 (4)
H13	0.2239	0.9361	0.2121	0.076*
C14	0.62123 (14)	0.7885 (2)	0.05441 (10)	0.0680 (4)
H14A	0.6063	0.8821	0.0915	0.102*
H14B	0.6879	0.8203	0.0346	0.102*
H14C	0.6384	0.6798	0.0884	0.102*
C15	0.43107 (18)	0.7894 (3)	−0.28053 (10)	0.0820 (5)
H15A	0.5134	0.8025	−0.2767	0.123*	0.5
H15B	0.3884	0.8953	−0.3062	0.123*	0.5
H15C	0.3981	0.6886	−0.3177	0.123*	0.5
H15D	0.3532	0.7884	−0.3237	0.123*	0.5
H15E	0.4782	0.6957	−0.2942	0.123*	0.5
H15F	0.4685	0.9023	−0.2827	0.123*	0.5
C16	0.44110 (17)	0.7610 (2)	0.49069 (11)	0.0781 (5)
H16A	0.4014	0.6596	0.5059	0.117*
H16B	0.4138	0.8679	0.512	0.117*
H16C	0.5254	0.7492	0.5183	0.117*
O1	0.40148 (9)	0.69351 (15)	0.07226 (6)	0.0647 (3)
O2	0.25305 (10)	0.88935 (17)	0.05767 (7)	0.0784 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0661 (9)	0.0529 (8)	0.0450 (8)	0.0106 (7)	0.0143 (6)	0.0031 (6)
C2	0.0564 (8)	0.0514 (8)	0.0461 (8)	0.0135 (6)	0.0092 (6)	0.0001 (6)
C3	0.0614 (9)	0.0608 (9)	0.0507 (8)	0.0127 (7)	0.0157 (7)	0.0010 (6)
C4	0.0715 (10)	0.0599 (9)	0.0454 (8)	0.0123 (7)	0.0111 (7)	−0.0027 (6)
C5	0.0696 (10)	0.0784 (11)	0.0503 (9)	0.0004 (8)	0.0004 (7)	−0.0058 (7)
C6	0.0607 (9)	0.0752 (11)	0.0612 (10)	−0.0030 (7)	0.0125 (7)	−0.0009 (8)
C7	0.0523 (8)	0.0551 (9)	0.0580 (8)	0.0018 (6)	0.0176 (6)	0.0054 (6)
C8	0.0521 (7)	0.0507 (8)	0.0537 (8)	−0.0020 (6)	0.0191 (6)	0.0046 (6)
C9	0.0560 (8)	0.0596 (9)	0.0561 (8)	0.0043 (6)	0.0215 (6)	0.0064 (7)
C10	0.0592 (8)	0.0648 (9)	0.0568 (9)	0.0011 (7)	0.0179 (7)	0.0098 (7)
C11	0.0710 (9)	0.0559 (9)	0.0548 (8)	−0.0110 (7)	0.0247 (7)	0.0020 (7)
C12	0.0757 (10)	0.0668 (10)	0.0682 (10)	0.0058 (8)	0.0367 (8)	0.0008 (8)
C13	0.0616 (8)	0.0649 (10)	0.0663 (9)	0.0112 (7)	0.0245 (7)	0.0082 (7)
C14	0.0628 (9)	0.0794 (11)	0.0526 (9)	0.0122 (8)	0.0041 (7)	0.0054 (7)
C15	0.0993 (13)	0.0965 (14)	0.0477 (9)	0.0158 (10)	0.0185 (9)	0.0004 (8)
C16	0.1006 (13)	0.0819 (12)	0.0553 (9)	−0.0093 (10)	0.0287 (9)	0.0016 (8)
O1	0.0757 (7)	0.0698 (7)	0.0500 (6)	0.0191 (5)	0.0213 (5)	0.0094 (5)
O2	0.0729 (7)	0.0965 (9)	0.0624 (7)	0.0288 (6)	0.0154 (5)	0.0131 (6)

Geometric parameters (Å, º) top

C1—C6	1.376 (2)	C10—C11	1.380 (2)
C1—C2	1.380 (2)	C10—H10	0.93
C1—O1	1.4075 (16)	C11—C12	1.384 (2)
C2—C3	1.3858 (19)	C11—C16	1.506 (2)
C2—C14	1.5023 (19)	C12—C13	1.375 (2)
C3—C4	1.385 (2)	C12—H12	0.93
C3—H3	0.93	C13—H13	0.93
C4—C5	1.381 (2)	C14—H14A	0.96
C4—C15	1.508 (2)	C14—H14B	0.96
C5—C6	1.380 (2)	C14—H14C	0.96
C5—H5	0.93	C15—H15A	0.96
C6—H6	0.93	C15—H15B	0.96
C7—O2	1.1982 (16)	C15—H15C	0.96
C7—O1	1.3519 (17)	C15—H15D	0.96
C7—C8	1.475 (2)	C15—H15E	0.96
C8—C13	1.388 (2)	C15—H15F	0.96
C8—C9	1.3889 (19)	C16—H16A	0.96
C9—C10	1.373 (2)	C16—H16B	0.96
C9—H9	0.93	C16—H16C	0.96

C6—C1—C2	122.28 (14)	C12—C13—H13	119.9
C6—C1—O1	121.70 (14)	C8—C13—H13	119.9
C2—C1—O1	115.94 (13)	C2—C14—H14A	109.5
C1—C2—C3	116.94 (13)	C2—C14—H14B	109.5
C1—C2—C14	121.63 (13)	H14A—C14—H14B	109.5
C3—C2—C14	121.43 (14)	C2—C14—H14C	109.5
C4—C3—C2	122.82 (15)	H14A—C14—H14C	109.5
C4—C3—H3	118.6	H14B—C14—H14C	109.5
C2—C3—H3	118.6	C4—C15—H15A	109.5
C5—C4—C3	117.76 (14)	C4—C15—H15B	109.5
C5—C4—C15	121.77 (14)	H15A—C15—H15B	109.5
C3—C4—C15	120.46 (15)	C4—C15—H15C	109.5
C6—C5—C4	121.29 (14)	H15A—C15—H15C	109.5
C6—C5—H5	119.4	H15B—C15—H15C	109.5
C4—C5—H5	119.4	C4—C15—H15D	109.5
C1—C6—C5	118.88 (15)	H15A—C15—H15D	141.1
C1—C6—H6	120.6	H15B—C15—H15D	56.3
C5—C6—H6	120.6	H15C—C15—H15D	56.3
O2—C7—O1	123.10 (13)	C4—C15—H15E	109.5
O2—C7—C8	125.31 (13)	H15A—C15—H15E	56.3
O1—C7—C8	111.59 (12)	H15B—C15—H15E	141.1
C13—C8—C9	118.54 (13)	H15C—C15—H15E	56.3
C13—C8—C7	118.51 (13)	H15D—C15—H15E	109.5
C9—C8—C7	122.93 (13)	C4—C15—H15F	109.5
C10—C9—C8	120.28 (14)	H15A—C15—H15F	56.3
C10—C9—H9	119.9	H15B—C15—H15F	56.3
C8—C9—H9	119.9	H15C—C15—H15F	141.1
C9—C10—C11	121.70 (14)	H15D—C15—H15F	109.5
C9—C10—H10	119.1	H15E—C15—H15F	109.5
C11—C10—H10	119.1	C11—C16—H16A	109.5
C10—C11—C12	117.70 (14)	C11—C16—H16B	109.5
C10—C11—C16	121.25 (15)	H16A—C16—H16B	109.5
C12—C11—C16	121.04 (14)	C11—C16—H16C	109.5
C13—C12—C11	121.51 (14)	H16A—C16—H16C	109.5
C13—C12—H12	119.2	H16B—C16—H16C	109.5
C11—C12—H12	119.2	C7—O1—C1	119.70 (11)
C12—C13—C8	120.27 (14)

C6—C1—C2—C3	1.2 (2)	O1—C7—C8—C9	6.60 (19)
O1—C1—C2—C3	178.26 (12)	C13—C8—C9—C10	0.4 (2)
C6—C1—C2—C14	−179.04 (14)	C7—C8—C9—C10	178.54 (13)
O1—C1—C2—C14	−2.0 (2)	C8—C9—C10—C11	−0.1 (2)
C1—C2—C3—C4	0.3 (2)	C9—C10—C11—C12	−0.1 (2)
C14—C2—C3—C4	−179.44 (14)	C9—C10—C11—C16	178.61 (14)
C2—C3—C4—C5	−1.5 (2)	C10—C11—C12—C13	−0.1 (2)
C2—C3—C4—C15	178.28 (14)	C16—C11—C12—C13	−178.80 (15)
C3—C4—C5—C6	1.2 (2)	C11—C12—C13—C8	0.4 (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—C1	13.5 (2)
C4—C5—C6—C1	0.2 (3)	C8—C7—O1—C1	−166.00 (12)
O2—C7—C8—C13	5.2 (2)	C6—C1—O1—C7	−62.88 (19)
O1—C7—C8—C13	−175.27 (13)	C2—C1—O1—C7	120.07 (15)
O2—C7—C8—C9	−172.89 (15)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆O₂
M_r	240.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	11.8022 (3), 7.4959 (2), 15.6288 (4)
β (°)	107.760 (3)
V (Å³)	1316.75 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.52 × 0.38 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur2 diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.96, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	15897, 2497, 1917
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.126, 1.09
No. of reflections	2497
No. of parameters	167
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

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 purchasing the diffractometer.

References

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