2,5-Dimethyl­phenyl benzoate

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

doi:10.1107/S1600536809010976

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o915

doi:10.1107/S1600536809010976

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2,5-Dimethylphenyl benzoate

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 15 March 2009; accepted 25 March 2009; online 28 March 2009)

In the title compound, C₁₅H₁₄O₂, the plane of the central –C(=O)–O– group is inclined at an angle of 3.7 (2)° with respect to the benzoate ring. The two benzene rings are almost perpendicular, making a dihedral angle of 87.4 (1)°. In the crystal, molecules are packed into infinite chains through weak C—H⋯π interactions.

Related literature

For the preparation of the compound, see: Nayak & Gowda (2009 ); For related structures, see: Gowda et al. (2008a ,b ).

Experimental

Crystal data

C₁₅H₁₄O₂
M_r = 226.26
Monoclinic, P 2₁ /c
a = 8.1095 (4) Å
b = 9.8569 (4) Å
c = 15.8805 (10) Å
β = 105.617 (5)°
V = 1222.54 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.51 × 0.37 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Mo) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.958, T_max = 0.982
29473 measured reflections
2330 independent reflections
1890 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.108
S = 1.07
2330 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯CT1ⁱ	0.93	2.92	3.7477 (14)	148
C6—H6⋯CT1ⁱⁱ	0.93	2.91	3.6495 (14)	137
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ . CT1 is the centroid of the benzoate ring C8–C13.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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: 10.1107/S1600536809010976/dn2434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010976/dn2434Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the solid state geometries of aryl benzoates (Gowda et al., 2008a, b), in the present work, the structure of 2,5-dimethylphenyl benzoate (25DMPBA) has been determined. The structure of 25DMPBA (Fig. 1) is similar to those of 2,3-dimethylphenyl benzoate (23DMPBA) (Gowda et al., 2008a), 2,4-dimethylphenyl benzoate (24DMPBA) (Gowda et al., 2008b) and other aryl benzoates. The plane of central –O—C—O– group in 25DMPBA makes the dihedral angle of 3.7 (2)° with respect to the benzoate ring, compared with the value of 5.7 (1)° in the structure of 24DMPBA. The two aromatic rings in 25DMPBA form a dihedral angle of 87.4 (1)°, in comparison with the corresponding angle of 80.3 (1)° in 24DMPBA. The other bond parameters in 25DMPBA are similar to those in 23DMPBA, 24DMPBA and other aryl benzoates.

The molecules in the structure are packed into infinite chains through weak C-H···π interactions between some H atoms of the phenyl ring and the benzoate ring centroids. The first intermoleculer interaction includes the atoms C3, H3 and the benzoate ring centroid CT1 at the symmetry position (x-1,y,z). The second interaction includes C6, H6 and the benzoate ring centroid CT1 at the position (x,-y+3/2,z+1/2)(Fig. 2).

Related literature top

For the preparation of the compound, see: Nayak & Gowda (2009); For related structures, see: Gowda et al. (2008a,b). CT1 is the centroid of the benzoate ring C8–C13.

Experimental top

The title compound was prepared according to a 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). 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.

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 (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of (I) viewed down the b axis. Infinite chains generated via C-H···π interactions are shown as dotted lines. CT1 is the benzoate ring (C8 to C13) centroid. H atoms not involved in hydrogen bonding were omitted. [Symmetry codes: (i) x-1,y,z; (ii) x,-y+3/2,z+1/2].

2,5-Dimethylphenyl benzoate top

Crystal data top

C₁₅H₁₄O₂	F(000) = 480
M_r = 226.26	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15569 reflections
a = 8.1095 (4) Å	θ = 3.2–29.5°
b = 9.8569 (4) Å	µ = 0.08 mm⁻¹
c = 15.8805 (10) Å	T = 295 K
β = 105.617 (5)°	Block, colourless
V = 1222.54 (11) Å³	0.51 × 0.37 × 0.28 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Mo) detector	2330 independent reflections
Graphite monochromator	1890 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.025
ω scans	θ_max = 25.9°, θ_min = 4.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
T_min = 0.958, T_max = 0.982	k = −12→12
29473 measured reflections	l = −19→19

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.051P)² + 0.1667P] where P = (F_o² + 2F_c²)/3
2330 reflections	(Δ/σ)_max < 0.001
156 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.10 e Å⁻³

Crystal data top

C₁₅H₁₄O₂	V = 1222.54 (11) Å³
M_r = 226.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1095 (4) Å	µ = 0.08 mm⁻¹
b = 9.8569 (4) Å	T = 295 K
c = 15.8805 (10) Å	0.51 × 0.37 × 0.28 mm
β = 105.617 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Mo) detector	2330 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1890 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.982	R_int = 0.025
29473 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.07	Δρ_max = 0.14 e Å⁻³
2330 reflections	Δρ_min = −0.10 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
O1	0.08573 (11)	0.73415 (10)	0.37466 (6)	0.0590 (3)
O2	−0.16712 (13)	0.79648 (13)	0.28463 (7)	0.0766 (3)
C1	−0.08701 (16)	0.75141 (14)	0.35356 (8)	0.0522 (3)
C2	−0.16012 (16)	0.70922 (12)	0.42546 (8)	0.0478 (3)
C3	−0.33645 (17)	0.71460 (15)	0.41159 (9)	0.0586 (4)
H3	−0.4058	0.7447	0.3583	0.070*
C4	−0.40821 (19)	0.67532 (17)	0.47672 (10)	0.0671 (4)
H4	−0.5264	0.6778	0.4673	0.080*
C5	−0.30493 (19)	0.63207 (16)	0.55630 (10)	0.0669 (4)
H5	−0.3540	0.6058	0.6004	0.080*
C6	−0.13073 (18)	0.62763 (15)	0.57060 (9)	0.0606 (4)
H6	−0.0618	0.5993	0.6245	0.073*
C7	−0.05770 (17)	0.66498 (13)	0.50552 (8)	0.0520 (3)
H7	0.0605	0.6606	0.5151	0.062*
C8	0.16784 (16)	0.77386 (14)	0.31055 (8)	0.0529 (3)
C9	0.22655 (16)	0.90581 (15)	0.31172 (8)	0.0577 (3)
C10	0.30805 (18)	0.93723 (17)	0.24763 (9)	0.0665 (4)
H10	0.3487	1.0249	0.2449	0.080*
C11	0.33025 (18)	0.84237 (19)	0.18820 (9)	0.0681 (4)
H11	0.3845	0.8677	0.1460	0.082*
C12	0.27415 (17)	0.71068 (17)	0.18959 (9)	0.0626 (4)
C13	0.19194 (17)	0.67728 (15)	0.25320 (8)	0.0570 (3)
H13	0.1533	0.5892	0.2567	0.068*
C14	0.2076 (2)	1.00775 (18)	0.37817 (11)	0.0801 (5)
H14A	0.0973	0.9975	0.3890	0.120*
H14B	0.2175	1.0975	0.3566	0.120*
H14C	0.2956	0.9938	0.4316	0.120*
C15	0.2950 (2)	0.6074 (2)	0.12344 (11)	0.0871 (5)
H15A	0.1904	0.6008	0.0776	0.131*
H15B	0.3217	0.5207	0.1514	0.131*
H15C	0.3862	0.6348	0.0992	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0521 (5)	0.0796 (6)	0.0484 (5)	0.0000 (4)	0.0188 (4)	0.0125 (4)
O2	0.0609 (6)	0.1169 (9)	0.0518 (6)	0.0068 (6)	0.0147 (5)	0.0194 (6)
C1	0.0531 (7)	0.0587 (7)	0.0451 (7)	−0.0021 (6)	0.0138 (6)	−0.0006 (6)
C2	0.0517 (7)	0.0480 (7)	0.0454 (6)	−0.0037 (5)	0.0159 (5)	−0.0056 (5)
C3	0.0530 (7)	0.0680 (9)	0.0545 (8)	−0.0003 (6)	0.0137 (6)	−0.0014 (6)
C4	0.0521 (8)	0.0831 (10)	0.0720 (9)	−0.0040 (7)	0.0269 (7)	−0.0051 (8)
C5	0.0696 (9)	0.0770 (9)	0.0643 (9)	−0.0056 (7)	0.0357 (7)	0.0002 (7)
C6	0.0664 (9)	0.0697 (9)	0.0487 (7)	0.0003 (7)	0.0204 (6)	0.0034 (6)
C7	0.0517 (7)	0.0576 (7)	0.0484 (7)	−0.0025 (6)	0.0163 (5)	−0.0028 (6)
C8	0.0455 (7)	0.0698 (8)	0.0432 (6)	−0.0006 (6)	0.0116 (5)	0.0114 (6)
C9	0.0513 (7)	0.0689 (8)	0.0492 (7)	−0.0028 (6)	0.0070 (6)	0.0075 (6)
C10	0.0558 (8)	0.0794 (10)	0.0607 (8)	−0.0133 (7)	0.0096 (7)	0.0171 (7)
C11	0.0494 (8)	0.1034 (12)	0.0545 (8)	−0.0048 (8)	0.0190 (6)	0.0147 (8)
C12	0.0476 (7)	0.0890 (11)	0.0518 (7)	0.0099 (7)	0.0144 (6)	0.0083 (7)
C13	0.0521 (7)	0.0665 (8)	0.0527 (7)	0.0014 (6)	0.0146 (6)	0.0075 (6)
C14	0.0914 (12)	0.0787 (11)	0.0666 (9)	−0.0073 (9)	0.0153 (8)	−0.0050 (8)
C15	0.0837 (12)	0.1139 (14)	0.0708 (10)	0.0228 (10)	0.0329 (9)	−0.0025 (10)

Geometric parameters (Å, º) top

O1—C1	1.3605 (16)	C8—C9	1.383 (2)
O1—C8	1.4136 (15)	C9—C10	1.3895 (19)
O2—C1	1.1977 (16)	C9—C14	1.495 (2)
C1—C2	1.4807 (17)	C10—C11	1.374 (2)
C2—C3	1.3880 (18)	C10—H10	0.9300
C2—C7	1.3885 (18)	C11—C12	1.378 (2)
C3—C4	1.372 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.3913 (19)
C4—C5	1.382 (2)	C12—C15	1.505 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.370 (2)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.3727 (18)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—C13	1.367 (2)	C15—H15C	0.9600

C1—O1—C8	116.19 (10)	C8—C9—C14	122.75 (13)
O2—C1—O1	122.74 (12)	C10—C9—C14	121.80 (14)
O2—C1—C2	125.28 (12)	C11—C10—C9	121.83 (14)
O1—C1—C2	111.98 (10)	C11—C10—H10	119.1
C3—C2—C7	119.61 (12)	C9—C10—H10	119.1
C3—C2—C1	118.43 (11)	C10—C11—C12	121.67 (13)
C7—C2—C1	121.96 (11)	C10—C11—H11	119.2
C4—C3—C2	119.83 (13)	C12—C11—H11	119.2
C4—C3—H3	120.1	C11—C12—C13	117.36 (14)
C2—C3—H3	120.1	C11—C12—C15	121.77 (14)
C3—C4—C5	120.05 (13)	C13—C12—C15	120.84 (15)
C3—C4—H4	120.0	C8—C13—C12	120.07 (14)
C5—C4—H4	120.0	C8—C13—H13	120.0
C6—C5—C4	120.36 (13)	C12—C13—H13	120.0
C6—C5—H5	119.8	C9—C14—H14A	109.5
C4—C5—H5	119.8	C9—C14—H14B	109.5
C5—C6—C7	120.09 (13)	H14A—C14—H14B	109.5
C5—C6—H6	120.0	C9—C14—H14C	109.5
C7—C6—H6	120.0	H14A—C14—H14C	109.5
C6—C7—C2	120.05 (12)	H14B—C14—H14C	109.5
C6—C7—H7	120.0	C12—C15—H15A	109.5
C2—C7—H7	120.0	C12—C15—H15B	109.5
C13—C8—C9	123.58 (12)	H15A—C15—H15B	109.5
C13—C8—O1	117.80 (12)	C12—C15—H15C	109.5
C9—C8—O1	118.54 (12)	H15A—C15—H15C	109.5
C8—C9—C10	115.44 (14)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···CT1ⁱ	0.93	2.92	3.7477 (14)	148
C6—H6···CT1ⁱⁱ	0.93	2.91	3.6495 (14)	137

Symmetry codes: (i) x−1, y, z; (ii) x, −y+3/2, z+1/2.

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)	8.1095 (4), 9.8569 (4), 15.8805 (10)
β (°)	105.617 (5)
V (Å³)	1222.54 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.51 × 0.37 × 0.28

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Mo) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.958, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	29473, 2330, 1890
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.108, 1.07
No. of reflections	2330
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.10

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).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···CT1ⁱ	0.93	2.92	3.7477 (14)	148.2
C6—H6···CT1ⁱⁱ	0.93	2.91	3.6495 (14)	137.0

Symmetry codes: (i) x−1, y, z; (ii) x, −y+3/2, z+1/2.

Acknowledgements

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 purchasing the diffractometer.

References

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