2,3-Dimethyl­phenyl benzoate

Gowda, B.T.; Foro, S.; Babitha, K.S.; Fuess, H.

doi:10.1107/S160053680800963X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o844

doi:10.1107/S160053680800963X

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2,3-Dimethylphenyl benzoate

B. Thimme Gowda,^a ^* Sabine Foro,^b K. S. Babitha ^a and Hartmut Fuess ^b

^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 28 March 2008; accepted 7 April 2008; online 16 April 2008)

The structure of the title compound (23DMPBA), C₁₅H₁₄O₂, resembles those of phenyl benzoate (PBA), 3-methylphenyl benzoate (3MePBA), 2,6-dichlorophenyl benzoate (26DCPBA) and other aryl benzoates, with similar bond parameters. The dihedral angle between the benzene and benzoyl rings in 23DMPBA is 87.36 (6)°, compared with values of 55.7° in PBA, 79.61 (6)° in 3MePBA and 75.75 (10)° in 26DCPBA. The molecules in 23DMPBA are packed into a chain-like structure in the direction of the a axis.

Related literature

For related literature, see: Adams & Morsi (1976 ); Gowda et al. (2007a ,b ); Nayak & Gowda (2008 ).

Experimental

Crystal data

C₁₅H₁₄O₂
M_r = 226.26
Monoclinic, C 2/c
a = 15.190 (2) Å
b = 8.417 (1) Å
c = 20.604 (2) Å
β = 112.20 (1)°
V = 2439.0 (5) Å³
Z = 8
Cu Kα radiation
μ = 0.65 mm⁻¹
T = 299 (2) K
0.50 × 0.44 × 0.36 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2328 measured reflections
2173 independent reflections
1886 reflections with I > 2σ(I)
R_int = 0.083
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.157
S = 1.07
2173 reflections
181 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800963X/om2224sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800963X/om2224Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of the substituent effects on the structures of aryl benzoates (Gowda et al., 2007a,b), the structure of 2,3-dimethylphenyl benzoate (23DMPBA) has been determined. The structure of 23DMPBA (Fig. 1) is similar to those of phenyl benzoate (PBA) (Adams & Morsi, 1976); 3-methylphenyl benzoate (3MePBA) (Gowda et al., 2007a), 2,3-dichlorophenyl benzoate (23DCPBA), 2,6-dichlorophenyl benzoate (26DCPBA) and other aryl benzoates (Gowda et al., 2007b). The bond parameters in 23DMPBA are similar to those in PBA, 3MePBA, 23DCPBA, 26DCPBA and other aryl benzoates. The dihedral angle between the benzene and benzoyl rings in 23DMPBA is 87.36 (6)°, compared to the values of 55.7° in PBA, 79.61 (6)° in 3MePBA and 75.75 (10)° in 26DCPBA. The molecules in the title compound are packed with the 2,3-dimethylphenyl and the benzoyl rings nearly orthogonal to each other, in the direction of the a axis (Fig. 2).

Related literature top

For related literature, see: Adams & Morsi (1976); Gowda et al. (2007a,b); 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.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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

	Fig. 1. Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound as viewed down a axis.
	Fig. 3. View of the molecule in the unit cell.

2,3-Dimethylphenyl benzoate top

Crystal data top

C₁₅H₁₄O₂	F(000) = 960
M_r = 226.26	D_x = 1.232 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 15.190 (2) Å	θ = 6.1–21.6°
b = 8.417 (1) Å	µ = 0.65 mm⁻¹
c = 20.604 (2) Å	T = 299 K
β = 112.20 (1)°	Prism, colourless
V = 2439.0 (5) Å³	0.50 × 0.44 × 0.36 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.083
Radiation source: fine-focus sealed tube	θ_max = 66.9°, θ_min = 4.6°
Graphite monochromator	h = −18→1
ω/2θ scans	k = −10→0
2328 measured reflections	l = −23→24
2173 independent reflections	3 standard reflections every 120 min
1886 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.157	w = 1/[σ²(F_o²) + (0.0825P)² + 1.2712P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.037
2173 reflections	Δρ_max = 0.17 e Å⁻³
181 parameters	Δρ_min = −0.17 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: 0.0061 (5)

Crystal data top

C₁₅H₁₄O₂	V = 2439.0 (5) Å³
M_r = 226.26	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 15.190 (2) Å	µ = 0.65 mm⁻¹
b = 8.417 (1) Å	T = 299 K
c = 20.604 (2) Å	0.50 × 0.44 × 0.36 mm
β = 112.20 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.083
2328 measured reflections	3 standard reflections every 120 min
2173 independent reflections	intensity decay: none
1886 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.17 e Å⁻³
2173 reflections	Δρ_min = −0.17 e Å⁻³
181 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
C1	0.11995 (13)	0.7351 (2)	0.40638 (10)	0.0564 (5)
C2	0.11817 (13)	0.6814 (2)	0.46975 (10)	0.0595 (5)
C3	0.17181 (15)	0.5454 (2)	0.49885 (10)	0.0642 (5)
C4	0.22248 (16)	0.4726 (3)	0.46390 (12)	0.0704 (6)
H4	0.2630 (18)	0.381 (3)	0.4882 (13)	0.085*
C5	0.22058 (17)	0.5274 (3)	0.40080 (12)	0.0715 (6)
H5	0.2588 (18)	0.475 (3)	0.3809 (14)	0.086*
C6	0.16888 (15)	0.6605 (3)	0.37155 (11)	0.0649 (5)
H6	0.1671 (17)	0.701 (3)	0.3293 (13)	0.078*
C7	−0.01527 (13)	0.8854 (2)	0.33725 (10)	0.0567 (5)
C8	−0.04911 (12)	1.0494 (2)	0.31758 (9)	0.0504 (4)
C9	0.00808 (13)	1.1812 (2)	0.34477 (10)	0.0564 (5)
H9	0.0723 (16)	1.168 (3)	0.3779 (11)	0.068*
C10	−0.02700 (15)	1.3317 (2)	0.32619 (11)	0.0623 (5)
H10	0.0154 (16)	1.430 (3)	0.3487 (12)	0.075*
C11	−0.11960 (15)	1.3535 (3)	0.28000 (11)	0.0631 (5)
H11	−0.1449 (17)	1.458 (3)	0.2661 (13)	0.076*
C12	−0.17667 (14)	1.2230 (3)	0.25200 (11)	0.0645 (5)
H12	−0.2430 (17)	1.236 (3)	0.2159 (13)	0.077*
C13	−0.14166 (13)	1.0727 (3)	0.27052 (11)	0.0591 (5)
H13	−0.1795 (16)	0.987 (3)	0.2533 (12)	0.071*
C14	0.06335 (18)	0.7675 (4)	0.50556 (15)	0.0871 (8)
H14A	0.0134	0.7002	0.5076	0.105*
H14B	0.0362	0.8622	0.4798	0.105*
H14C	0.1051	0.7954	0.5522	0.105*
C15	0.1773 (2)	0.4813 (3)	0.56843 (13)	0.0935 (8)
H15A	0.1143	0.4629	0.5670	0.112*
H15B	0.2091	0.5568	0.6046	0.112*
H15C	0.2121	0.3831	0.5780	0.112*
O1	0.07702 (9)	0.88173 (15)	0.37981 (8)	0.0675 (4)
O2	−0.06258 (11)	0.76695 (18)	0.31914 (10)	0.0883 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0502 (9)	0.0455 (9)	0.0609 (10)	−0.0046 (7)	0.0065 (8)	−0.0017 (8)
C2	0.0535 (10)	0.0564 (11)	0.0610 (11)	−0.0095 (8)	0.0129 (8)	−0.0072 (8)
C3	0.0677 (11)	0.0563 (11)	0.0564 (10)	−0.0138 (9)	0.0095 (9)	0.0000 (8)
C4	0.0738 (13)	0.0501 (11)	0.0703 (13)	0.0013 (10)	0.0079 (10)	−0.0009 (9)
C5	0.0752 (13)	0.0619 (12)	0.0719 (13)	0.0045 (10)	0.0217 (11)	−0.0120 (10)
C6	0.0691 (12)	0.0617 (12)	0.0573 (11)	−0.0039 (9)	0.0164 (9)	−0.0044 (9)
C7	0.0490 (9)	0.0546 (11)	0.0584 (10)	−0.0054 (8)	0.0112 (8)	−0.0043 (8)
C8	0.0471 (9)	0.0549 (10)	0.0493 (9)	−0.0032 (7)	0.0182 (7)	−0.0015 (7)
C9	0.0490 (9)	0.0566 (11)	0.0596 (10)	−0.0050 (8)	0.0158 (8)	−0.0020 (8)
C10	0.0629 (11)	0.0524 (11)	0.0707 (12)	−0.0060 (9)	0.0244 (9)	−0.0003 (9)
C11	0.0648 (12)	0.0569 (11)	0.0691 (12)	0.0077 (9)	0.0271 (10)	0.0086 (9)
C12	0.0511 (10)	0.0692 (12)	0.0668 (12)	0.0066 (9)	0.0148 (9)	0.0069 (9)
C13	0.0471 (9)	0.0610 (11)	0.0645 (11)	−0.0054 (8)	0.0157 (8)	−0.0020 (9)
C14	0.0745 (14)	0.0993 (19)	0.0908 (17)	−0.0057 (13)	0.0348 (13)	−0.0173 (14)
C15	0.111 (2)	0.0891 (17)	0.0706 (14)	−0.0173 (15)	0.0230 (13)	0.0152 (13)
O1	0.0532 (7)	0.0483 (8)	0.0808 (9)	−0.0021 (5)	0.0025 (6)	0.0035 (6)
O2	0.0634 (9)	0.0556 (9)	0.1143 (13)	−0.0099 (7)	−0.0022 (8)	−0.0049 (8)

Geometric parameters (Å, º) top

C1—C6	1.365 (3)	C8—C9	1.390 (2)
C1—C2	1.391 (3)	C9—C10	1.372 (3)
C1—O1	1.407 (2)	C9—H9	0.96 (2)
C2—C3	1.402 (3)	C10—C11	1.381 (3)
C2—C14	1.492 (3)	C10—H10	1.04 (2)
C3—C4	1.380 (3)	C11—C12	1.383 (3)
C3—C15	1.504 (3)	C11—H11	0.96 (2)
C4—C5	1.369 (3)	C12—C13	1.370 (3)
C4—H4	1.00 (3)	C12—H12	1.01 (3)
C5—C6	1.370 (3)	C13—H13	0.91 (2)
C5—H5	0.94 (3)	C14—H14A	0.9600
C6—H6	0.92 (2)	C14—H14B	0.9600
C7—O2	1.203 (2)	C14—H14C	0.9600
C7—O1	1.344 (2)	C15—H15A	0.9600
C7—C8	1.475 (3)	C15—H15B	0.9600
C8—C13	1.387 (3)	C15—H15C	0.9600

C6—C1—C2	123.46 (19)	C8—C9—H9	120.3 (14)
C6—C1—O1	117.59 (18)	C9—C10—C11	120.18 (19)
C2—C1—O1	118.66 (18)	C9—C10—H10	119.9 (13)
C1—C2—C3	116.89 (19)	C11—C10—H10	119.9 (13)
C1—C2—C14	121.2 (2)	C10—C11—C12	119.76 (19)
C3—C2—C14	121.9 (2)	C10—C11—H11	121.1 (15)
C4—C3—C2	119.20 (19)	C12—C11—H11	119.1 (15)
C4—C3—C15	119.8 (2)	C13—C12—C11	120.09 (18)
C2—C3—C15	121.0 (2)	C13—C12—H12	118.8 (14)
C5—C4—C3	122.0 (2)	C11—C12—H12	121.0 (14)
C5—C4—H4	121.7 (14)	C12—C13—C8	120.62 (19)
C3—C4—H4	116.3 (14)	C12—C13—H13	120.3 (14)
C4—C5—C6	119.7 (2)	C8—C13—H13	119.0 (15)
C4—C5—H5	117.5 (16)	C2—C14—H14A	109.5
C6—C5—H5	122.7 (16)	C2—C14—H14B	109.5
C1—C6—C5	118.7 (2)	H14A—C14—H14B	109.5
C1—C6—H6	120.0 (15)	C2—C14—H14C	109.5
C5—C6—H6	121.3 (15)	H14A—C14—H14C	109.5
O2—C7—O1	122.50 (17)	H14B—C14—H14C	109.5
O2—C7—C8	125.80 (16)	C3—C15—H15A	109.5
O1—C7—C8	111.70 (15)	C3—C15—H15B	109.5
C13—C8—C9	118.88 (18)	H15A—C15—H15B	109.5
C13—C8—C7	118.69 (16)	C3—C15—H15C	109.5
C9—C8—C7	122.43 (16)	H15A—C15—H15C	109.5
C10—C9—C8	120.46 (17)	H15B—C15—H15C	109.5
C10—C9—H9	119.2 (14)	C7—O1—C1	119.33 (14)

C6—C1—C2—C3	1.5 (3)	O1—C7—C8—C13	176.36 (16)
O1—C1—C2—C3	−172.15 (15)	O2—C7—C8—C9	175.1 (2)
C6—C1—C2—C14	−179.93 (19)	O1—C7—C8—C9	−4.1 (3)
O1—C1—C2—C14	6.5 (3)	C13—C8—C9—C10	1.0 (3)
C1—C2—C3—C4	−0.2 (3)	C7—C8—C9—C10	−178.57 (18)
C14—C2—C3—C4	−178.79 (19)	C8—C9—C10—C11	−0.2 (3)
C1—C2—C3—C15	177.84 (19)	C9—C10—C11—C12	−0.6 (3)
C14—C2—C3—C15	−0.8 (3)	C10—C11—C12—C13	0.6 (3)
C2—C3—C4—C5	−1.3 (3)	C11—C12—C13—C8	0.3 (3)
C15—C3—C4—C5	−179.3 (2)	C9—C8—C13—C12	−1.0 (3)
C3—C4—C5—C6	1.5 (3)	C7—C8—C13—C12	178.55 (18)
C2—C1—C6—C5	−1.2 (3)	O2—C7—O1—C1	−2.1 (3)
O1—C1—C6—C5	172.43 (17)	C8—C7—O1—C1	177.08 (16)
C4—C5—C6—C1	−0.3 (3)	C6—C1—O1—C7	96.1 (2)
O2—C7—C8—C13	−4.5 (3)	C2—C1—O1—C7	−90.0 (2)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₂
M_r	226.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	299
a, b, c (Å)	15.190 (2), 8.417 (1), 20.604 (2)
β (°)	112.20 (1)
V (Å³)	2439.0 (5)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.50 × 0.44 × 0.36

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2328, 2173, 1886
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.157, 1.07
No. of reflections	2173
No. of parameters	181
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), 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

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