2,4-Dimethyl­phenyl benzoate

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Babitha, K.S.; Fuess, H.

doi:10.1107/S1600536808017480

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1280

doi:10.1107/S1600536808017480

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2,4-Dimethylphenyl benzoate

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b K. S. Babitha ^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 5 June 2008; accepted 10 June 2008; online 19 June 2008)

The crystal structure of the title compound (24DMPBA), C₁₅H₁₄O₂, resembles those of 4-methylphenyl benzoate, 2,3-dimethylphenyl benzoate and other aryl benzoates, with similar bond parameters. The central –O—C—O– group in 24DMPBA makes dihedral angles of 85.81 (5) and 5.71 (13)°, respectively, with the benzoyl and phenyl rings, while the two aromatic rings form a dihedral angle of 80.25 (5)°. The molecules are packed with their axes parallel to the a-axis direction.

Related literature

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

Experimental

Crystal data

C₁₅H₁₄O₂
M_r = 226.26
Monoclinic, P 2₁ /c
a = 7.9813 (2) Å
b = 14.3260 (3) Å
c = 11.0932 (2) Å
β = 94.028 (2)°
V = 1265.26 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 (2) K
0.48 × 0.38 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.965, T_max = 0.987
28657 measured reflections
2471 independent reflections
2056 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.134
S = 1.08
2471 reflections
156 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 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 ); 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, 2003 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017480/ci2614sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017480/ci2614Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of the substituent effects on the solid state geometries of aryl benzoates (Gowda et al., 2007, 2008), the structure of 2,4-dimethylphenyl benzoate (24DMPBA) has been determined. The structure of 24DMPBA (Fig. 1) is similar to those of 4-methylphenyl benzoate (4MePBA)(Gowda et al., 2007), 2,3-dimethylphenyl benzoate (23DMPBA) (Gowda et al., 2008) and other aryl benzoates. The central –O—C—O– group in 24DMPBA makes a dihedral angle of 85.81 (5)° with the benzoyl phenyl ring and 5.71 (13)° with the phenyl ring. The two aromatic rings in 24DMPBA form a dihedral angle of 80.25 (5)°. The bond parameters in 24DMPBA are similar to those in 4MePBA, 23DMPBA and other aryl benzoates. Part of the crystal structure of the title compound as viewed along the a axis 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 were obtained by slow evaporation of an ethanolic solution and used for X-ray diffraction studies at room temperature.

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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) 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 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of the title compound as viewed along the a axis. H atoms have been omitted for the sake of clarity.

2,4-Dimethylphenyl benzoate top

Crystal data top

C₁₅H₁₄O₂	F(000) = 480
M_r = 226.26	D_x = 1.188 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12993 reflections
a = 7.9813 (2) Å	θ = 3.2–29.3°
b = 14.3260 (3) Å	µ = 0.08 mm⁻¹
c = 11.0932 (2) Å	T = 295 K
β = 94.028 (2)°	Block, colourless
V = 1265.26 (5) Å³	0.48 × 0.38 × 0.21 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer	2471 independent reflections
Graphite monochromator	2056 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.031
ω scans with κ offsets	θ_max = 26.0°, θ_min = 5.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −9→9
T_min = 0.965, T_max = 0.987	k = −17→17
28657 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0541P)² + 0.2483P] where P = (F_o² + 2F_c²)/3
2471 reflections	(Δ/σ)_max = 0.001
156 parameters	Δρ_max = 0.16 e Å⁻³
4 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₅H₁₄O₂	V = 1265.26 (5) Å³
M_r = 226.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9813 (2) Å	µ = 0.08 mm⁻¹
b = 14.3260 (3) Å	T = 295 K
c = 11.0932 (2) Å	0.48 × 0.38 × 0.21 mm
β = 94.028 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	2471 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2056 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.987	R_int = 0.031
28657 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	4 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.08	Δρ_max = 0.16 e Å⁻³
2471 reflections	Δρ_min = −0.15 e Å⁻³
156 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)
O1	0.77410 (13)	0.30501 (7)	0.43628 (10)	0.0642 (3)
O2	0.56045 (16)	0.31504 (8)	0.29564 (11)	0.0795 (4)
C1	0.65706 (18)	0.35245 (10)	0.36678 (13)	0.0540 (4)
C2	0.66645 (18)	0.45392 (10)	0.38934 (13)	0.0529 (4)
C3	0.5646 (2)	0.51221 (12)	0.31812 (17)	0.0750 (5)
H3	0.4919	0.4871	0.2574	0.09*
C4	0.5690 (3)	0.60709 (14)	0.3358 (2)	0.0901 (6)
H4	0.5004	0.6458	0.2865	0.108*
C5	0.6720 (3)	0.64395 (12)	0.4237 (3)	0.0912 (7)
H5	0.6748	0.7082	0.4353	0.109*
C6	0.7731 (3)	0.58741 (14)	0.4966 (2)	0.0971 (7)
H6	0.8437	0.6134	0.5579	0.116*
C7	0.7711 (2)	0.49201 (12)	0.47963 (18)	0.0738 (5)
H7	0.8402	0.4537	0.5292	0.089*
C8	0.77716 (18)	0.20698 (10)	0.42443 (13)	0.0552 (4)
C9	0.8731 (2)	0.16674 (11)	0.34018 (14)	0.0623 (4)
C10	0.8778 (2)	0.06901 (12)	0.33938 (17)	0.0732 (5)
H10	0.9403	0.0392	0.2831	0.088*
C11	0.7940 (2)	0.01520 (12)	0.41818 (18)	0.0759 (5)
C12	0.7035 (2)	0.05916 (12)	0.50064 (19)	0.0786 (5)
H12	0.6473	0.0239	0.5555	0.094*
C13	0.6936 (2)	0.15527 (12)	0.50441 (16)	0.0682 (4)
H13	0.6306	0.1845	0.5609	0.082*
C14	0.9689 (3)	0.22412 (17)	0.2560 (2)	0.0964 (6)
H14A	0.9884	0.1881	0.1854	0.145*	0.56 (3)
H14B	1.0745	0.2423	0.2958	0.145*	0.56 (3)
H14C	0.9052	0.2789	0.2328	0.145*	0.56 (3)
H14D	0.9904	0.2847	0.2906	0.145*	0.44 (3)
H14E	0.9042	0.2305	0.1802	0.145*	0.44 (3)
H14F	1.0735	0.1939	0.2432	0.145*	0.44 (3)
C15	0.8030 (3)	−0.09032 (13)	0.4133 (3)	0.1179 (10)
H15A	0.771	−0.1159	0.4884	0.177*	0.67 (3)
H15B	0.9157	−0.1092	0.4002	0.177*	0.67 (3)
H15C	0.7279	−0.1128	0.3484	0.177*	0.67 (3)
H15D	0.8387	−0.1094	0.3362	0.177*	0.33 (3)
H15E	0.6941	−0.1161	0.4244	0.177*	0.33 (3)
H15F	0.8818	−0.1124	0.4762	0.177*	0.33 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0729 (7)	0.0412 (5)	0.0751 (7)	0.0067 (5)	−0.0183 (5)	−0.0071 (5)
O2	0.0873 (8)	0.0582 (7)	0.0878 (8)	0.0055 (6)	−0.0314 (7)	−0.0134 (6)
C1	0.0571 (8)	0.0488 (8)	0.0553 (8)	0.0039 (6)	−0.0018 (7)	−0.0026 (6)
C2	0.0542 (8)	0.0450 (7)	0.0601 (8)	0.0017 (6)	0.0072 (6)	0.0017 (6)
C3	0.0791 (11)	0.0585 (10)	0.0857 (12)	0.0119 (8)	−0.0066 (9)	0.0087 (8)
C4	0.0900 (14)	0.0574 (11)	0.1237 (17)	0.0170 (10)	0.0124 (13)	0.0235 (11)
C5	0.0875 (13)	0.0391 (9)	0.151 (2)	−0.0004 (9)	0.0357 (14)	0.0035 (11)
C6	0.1008 (15)	0.0578 (11)	0.1305 (18)	−0.0126 (10)	−0.0065 (13)	−0.0219 (11)
C7	0.0802 (11)	0.0480 (9)	0.0906 (12)	−0.0014 (8)	−0.0120 (9)	−0.0058 (8)
C8	0.0599 (9)	0.0420 (7)	0.0614 (9)	0.0049 (6)	−0.0113 (7)	−0.0057 (6)
C9	0.0636 (9)	0.0620 (9)	0.0598 (9)	0.0067 (7)	−0.0077 (7)	−0.0058 (7)
C10	0.0728 (11)	0.0665 (10)	0.0775 (11)	0.0210 (8)	−0.0152 (8)	−0.0246 (8)
C11	0.0760 (11)	0.0466 (9)	0.0998 (13)	0.0052 (7)	−0.0321 (9)	−0.0061 (8)
C12	0.0782 (12)	0.0592 (10)	0.0962 (13)	−0.0084 (8)	−0.0077 (9)	0.0118 (9)
C13	0.0691 (10)	0.0601 (10)	0.0752 (11)	0.0040 (8)	0.0039 (8)	−0.0023 (8)
C14	0.1010 (15)	0.1049 (16)	0.0852 (13)	0.0047 (12)	0.0189 (11)	0.0038 (12)
C15	0.1271 (19)	0.0463 (10)	0.170 (2)	0.0118 (10)	−0.0637 (18)	−0.0131 (12)

Geometric parameters (Å, º) top

O1—C1	1.3519 (17)	C10—C11	1.374 (3)
O1—C8	1.4108 (17)	C10—H10	0.93
O2—C1	1.1913 (17)	C11—C12	1.359 (3)
C1—C2	1.476 (2)	C11—C15	1.514 (2)
C2—C7	1.371 (2)	C12—C13	1.380 (2)
C2—C3	1.376 (2)	C12—H12	0.93
C3—C4	1.373 (3)	C13—H13	0.93
C3—H3	0.93	C14—H14A	0.96
C4—C5	1.339 (3)	C14—H14B	0.96
C4—H4	0.93	C14—H14C	0.96
C5—C6	1.367 (3)	C14—H14D	0.96
C5—H5	0.93	C14—H14E	0.96
C6—C7	1.379 (3)	C14—H14F	0.96
C6—H6	0.93	C15—H15A	0.96
C7—H7	0.93	C15—H15B	0.96
C8—C13	1.365 (2)	C15—H15C	0.96
C8—C9	1.376 (2)	C15—H15D	0.96
C9—C10	1.401 (2)	C15—H15E	0.96
C9—C14	1.494 (3)	C15—H15F	0.96

C1—O1—C8	117.59 (11)	C9—C14—H14B	109.5
O2—C1—O1	122.74 (14)	H14A—C14—H14B	109.5
O2—C1—C2	125.32 (14)	C9—C14—H14C	109.5
O1—C1—C2	111.93 (12)	H14A—C14—H14C	109.5
C7—C2—C3	118.87 (15)	H14B—C14—H14C	109.5
C7—C2—C1	122.47 (14)	C9—C14—H14D	109.5
C3—C2—C1	118.65 (14)	H14A—C14—H14D	141.1
C4—C3—C2	120.70 (19)	H14B—C14—H14D	56.3
C4—C3—H3	119.7	H14C—C14—H14D	56.3
C2—C3—H3	119.7	C9—C14—H14E	109.5
C5—C4—C3	120.17 (19)	H14A—C14—H14E	56.3
C5—C4—H4	119.9	H14B—C14—H14E	141.1
C3—C4—H4	119.9	H14C—C14—H14E	56.3
C4—C5—C6	120.23 (17)	H14D—C14—H14E	109.5
C4—C5—H5	119.9	C9—C14—H14F	109.5
C6—C5—H5	119.9	H14A—C14—H14F	56.3
C5—C6—C7	120.4 (2)	H14B—C14—H14F	56.3
C5—C6—H6	119.8	H14C—C14—H14F	141.1
C7—C6—H6	119.8	H14D—C14—H14F	109.5
C2—C7—C6	119.64 (18)	H14E—C14—H14F	109.5
C2—C7—H7	120.2	C11—C15—H15A	109.5
C6—C7—H7	120.2	C11—C15—H15B	109.5
C13—C8—C9	122.33 (15)	H15A—C15—H15B	109.5
C13—C8—O1	117.84 (14)	C11—C15—H15C	109.5
C9—C8—O1	119.64 (14)	H15A—C15—H15C	109.5
C8—C9—C10	116.07 (16)	H15B—C15—H15C	109.5
C8—C9—C14	121.84 (16)	C11—C15—H15D	109.5
C10—C9—C14	122.09 (17)	H15A—C15—H15D	141.1
C11—C10—C9	122.86 (16)	H15B—C15—H15D	56.3
C11—C10—H10	118.6	H15C—C15—H15D	56.3
C9—C10—H10	118.6	C11—C15—H15E	109.5
C12—C11—C10	118.26 (16)	H15A—C15—H15E	56.3
C12—C11—C15	121.0 (2)	H15B—C15—H15E	141.1
C10—C11—C15	120.7 (2)	H15C—C15—H15E	56.3
C11—C12—C13	121.14 (18)	H15D—C15—H15E	109.5
C11—C12—H12	119.4	C11—C15—H15F	109.5
C13—C12—H12	119.4	H15A—C15—H15F	56.3
C8—C13—C12	119.34 (17)	H15B—C15—H15F	56.3
C8—C13—H13	120.3	H15C—C15—H15F	141.1
C12—C13—H13	120.3	H15D—C15—H15F	109.5
C9—C14—H14A	109.5	H15E—C15—H15F	109.5

C8—O1—C1—O2	−1.4 (2)	C1—O1—C8—C9	89.23 (17)
C8—O1—C1—C2	179.25 (12)	C13—C8—C9—C10	1.2 (2)
O2—C1—C2—C7	174.36 (17)	O1—C8—C9—C10	176.08 (13)
O1—C1—C2—C7	−6.4 (2)	C13—C8—C9—C14	−177.81 (16)
O2—C1—C2—C3	−4.7 (2)	O1—C8—C9—C14	−2.9 (2)
O1—C1—C2—C3	174.61 (14)	C8—C9—C10—C11	−0.7 (2)
C7—C2—C3—C4	0.9 (3)	C14—C9—C10—C11	178.30 (17)
C1—C2—C3—C4	−179.98 (17)	C9—C10—C11—C12	−0.3 (3)
C2—C3—C4—C5	−0.6 (3)	C9—C10—C11—C15	179.91 (16)
C3—C4—C5—C6	−0.1 (3)	C10—C11—C12—C13	0.9 (3)
C4—C5—C6—C7	0.5 (3)	C15—C11—C12—C13	−179.29 (17)
C3—C2—C7—C6	−0.5 (3)	C9—C8—C13—C12	−0.7 (2)
C1—C2—C7—C6	−179.57 (18)	O1—C8—C13—C12	−175.61 (14)
C5—C6—C7—C2	−0.2 (3)	C11—C12—C13—C8	−0.5 (3)
C1—O1—C8—C13	−95.67 (17)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₂
M_r	226.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.9813 (2), 14.3260 (3), 11.0932 (2)
β (°)	94.028 (2)
V (Å³)	1265.26 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.48 × 0.38 × 0.21

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.965, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	28657, 2471, 2056
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.134, 1.08
No. of reflections	2471
No. of parameters	156
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship. MT and JK thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in the purchase of the diffractometer.

References

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