4-Methyl­phenyl benzoate

The structure of the title compound (4MePBA), C₁₄H₁₂O₂, resembles those of phenyl benzoate (PBA) and 4-methoxy­phenyl benzoate (4MeOPBA), with similar geometric parameters. The dihedral angle between the phenyl and benzene rings in 4MePBA is 60.17 (7)°, compared with the values of 55.7° for PBA and 56.42 (3)° for 4MeOPBA. The mol­ecules in the title compound are packed with the methyl­phenyl rings parallel to the bc plane and the benzoyl rings perpendicular to this plane.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.142
• Data-to-parameter ratio = 12.0

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S1. Comment

In the present work, as part of a study of substituent effects on the solid state structures of chemically and industrially significant compounds (Gowda, Foro et al., 2007; Gowda, Kožíšek, Svoboda & Fuess, 2007; Gowda, Kožíšek, Tokarčík & Fuess, 2007; Gowda, Nayak et al., 2007; Gowda, Svoboda & Fuess, 2007; Gowda, Tokarčík et al., 2007) the structure of 4-methylphenyl benzoate (4MePBA) has been determined. The structure of 4MePBA (Fig. 1) is similar to that of phenyl benzoate (PBA) (Adams & Morsi, 1976) and 4-methoxylphenyl benzoate (4MeOPBA) (Gowda, Foro et al., 2007). The bond parameters in 4MePBA are similar to those in PBA and other benzoates. The molecules in the title compound are packed with the methylphenyl rings parallel to the bc plane and the benzoyl rings perpendicular to this plane (Fig. 2).

Related literature

For related literature, see: Adams & Morsi (1976); Gowda, Foro et al. (2007); Gowda, Kožíšek, Svoboda & Fuess (2007); Gowda, Kožíšek, Tokarčík & Fuess (2007); Gowda, Nayak et al. (2007); Gowda, Svoboda & Fuess (2007); Gowda, Tokarčík et al. (2007); Nayak & Gowda (2007).

S2. Experimental

The title compound was prepared according to a literature method (Nayak & Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Nayak & Gowda, 2007). 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.

S3. Refinement

The methyl H atoms were positioned with idealized geometry and refined using a riding model, with C—H = 0.96 Å. All other H atoms were located in a difference map and their positions refined freely [C—H = 0.93 (2)–1.01 (2) Å]. U_iso(H) values were set equal to 1.2U_eq of the parent atom.

Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius.
	Fig. 2. Molecular packing of the title compound.

4-Methylphenyl benzoate

Crystal data

C14H12O2	Z = 2
Mr = 212.24	F(000) = 224
Triclinic, P1	Dx = 1.205 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.1488 (9) Å	Cell parameters from 25 reflections
b = 9.052 (1) Å	θ = 6.2–25.2°
c = 9.299 (1) Å	µ = 0.64 mm^−1
α = 76.99 (2)°	T = 299 K
β = 68.73 (1)°	Prism, colourless
γ = 66.87 (1)°	0.60 × 0.48 × 0.40 mm
V = 585.08 (11) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1903 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 66.9°, θmin = 5.1°
ω/2θ scans	h = −9→8
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.671, Tmax = 0.773	l = −11→11
3995 measured reflections	3 standard reflections every 120 min
2082 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0629P)^2 + 0.0783P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.003
2082 reflections	Δρmax = 0.15 e Å^−3
174 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.173 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.31783 (19)	0.13239 (16)	0.74315 (17)	0.0559 (4)
C2	0.3400 (2)	0.14401 (19)	0.87892 (18)	0.0641 (4)
H2	0.275 (2)	0.092 (2)	0.978 (2)	0.077*
C3	0.4548 (2)	0.2249 (2)	0.8743 (2)	0.0678 (5)
H3	0.476 (3)	0.230 (2)	0.965 (2)	0.081*
C4	0.5471 (2)	0.29397 (17)	0.7360 (2)	0.0664 (5)
C5	0.5191 (2)	0.28167 (19)	0.6023 (2)	0.0714 (5)
H5	0.591 (3)	0.328 (2)	0.501 (2)	0.086*
C6	0.4059 (2)	0.20075 (19)	0.60421 (19)	0.0657 (4)
H6	0.385 (2)	0.197 (2)	0.512 (2)	0.079*
C7	0.24839 (19)	−0.10521 (17)	0.77574 (17)	0.0554 (4)
C8	0.11334 (17)	−0.16976 (16)	0.76323 (15)	0.0513 (4)
C9	−0.0320 (2)	−0.07552 (19)	0.70380 (18)	0.0586 (4)
H9	−0.051 (2)	0.035 (2)	0.6694 (19)	0.070*
C10	−0.1494 (2)	−0.1426 (2)	0.6884 (2)	0.0717 (5)
H10	−0.259 (3)	−0.071 (2)	0.651 (2)	0.086*
C11	−0.1205 (3)	−0.3043 (2)	0.7315 (2)	0.0759 (5)
H11	−0.202 (3)	−0.347 (2)	0.718 (2)	0.091*
C12	0.0232 (3)	−0.3988 (2)	0.7912 (2)	0.0769 (5)
H12	0.049 (3)	−0.513 (3)	0.821 (2)	0.092*
C13	0.1401 (2)	−0.33226 (19)	0.8085 (2)	0.0665 (4)
H13	0.241 (3)	−0.397 (2)	0.852 (2)	0.080*
C14	0.6715 (3)	0.3822 (2)	0.7336 (3)	0.0987 (7)
H14A	0.7406	0.3255	0.8056	0.118*
H14B	0.5957	0.4894	0.7624	0.118*
H14C	0.7573	0.3878	0.6311	0.118*
O1	0.19668 (14)	0.05681 (12)	0.74249 (14)	0.0658 (4)
O2	0.39043 (16)	−0.18510 (13)	0.80612 (16)	0.0797 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0542 (8)	0.0488 (8)	0.0726 (9)	−0.0214 (6)	−0.0256 (6)	−0.0032 (6)
C2	0.0688 (9)	0.0665 (10)	0.0645 (9)	−0.0329 (8)	−0.0210 (7)	−0.0014 (7)
C3	0.0751 (10)	0.0653 (10)	0.0781 (10)	−0.0277 (8)	−0.0346 (8)	−0.0101 (8)
C4	0.0583 (8)	0.0481 (8)	0.0975 (12)	−0.0215 (7)	−0.0233 (8)	−0.0108 (7)
C5	0.0809 (11)	0.0580 (9)	0.0749 (10)	−0.0359 (8)	−0.0124 (8)	−0.0026 (7)
C6	0.0837 (11)	0.0579 (9)	0.0645 (9)	−0.0316 (8)	−0.0279 (8)	−0.0004 (7)
C7	0.0514 (7)	0.0518 (8)	0.0671 (9)	−0.0184 (6)	−0.0232 (6)	−0.0034 (6)
C8	0.0475 (7)	0.0504 (8)	0.0579 (8)	−0.0201 (6)	−0.0150 (6)	−0.0042 (6)
C9	0.0587 (8)	0.0540 (8)	0.0702 (9)	−0.0243 (7)	−0.0262 (7)	0.0008 (6)
C10	0.0687 (10)	0.0750 (11)	0.0891 (11)	−0.0327 (8)	−0.0387 (8)	−0.0016 (8)
C11	0.0757 (11)	0.0762 (11)	0.0965 (13)	−0.0438 (9)	−0.0292 (9)	−0.0095 (9)
C12	0.0784 (11)	0.0546 (9)	0.1036 (13)	−0.0337 (8)	−0.0254 (9)	−0.0026 (8)
C13	0.0612 (9)	0.0531 (9)	0.0868 (11)	−0.0214 (7)	−0.0269 (8)	0.0009 (7)
C14	0.0816 (12)	0.0713 (12)	0.161 (2)	−0.0391 (10)	−0.0371 (12)	−0.0209 (12)
O1	0.0635 (6)	0.0525 (6)	0.0964 (8)	−0.0260 (5)	−0.0406 (6)	0.0030 (5)
O2	0.0681 (7)	0.0609 (7)	0.1268 (11)	−0.0191 (5)	−0.0553 (7)	−0.0029 (6)

Geometric parameters (Å, º)

C1—C2	1.370 (2)	C8—C9	1.380 (2)
C1—C6	1.372 (2)	C8—C13	1.387 (2)
C1—O1	1.4070 (16)	C9—C10	1.378 (2)
C2—C3	1.382 (2)	C9—H9	0.947 (18)
C2—H2	0.996 (18)	C10—C11	1.375 (3)
C3—C4	1.384 (2)	C10—H10	1.01 (2)
C3—H3	0.93 (2)	C11—C12	1.372 (3)
C4—C5	1.378 (2)	C11—H11	0.94 (2)
C4—C14	1.509 (2)	C12—C13	1.380 (2)
C5—C6	1.379 (2)	C12—H12	0.97 (2)
C5—H5	1.011 (19)	C13—H13	0.97 (2)
C6—H6	0.940 (19)	C14—H14A	0.9600
C7—O2	1.1958 (17)	C14—H14B	0.9600
C7—O1	1.3524 (17)	C14—H14C	0.9600
C7—C8	1.4814 (18)
C2—C1—C6	121.18 (14)	C13—C8—C7	117.90 (13)
C2—C1—O1	121.05 (13)	C10—C9—C8	120.23 (15)
C6—C1—O1	117.70 (13)	C10—C9—H9	118.6 (10)
C1—C2—C3	118.91 (15)	C8—C9—H9	121.1 (10)
C1—C2—H2	119.4 (10)	C11—C10—C9	119.77 (16)
C3—C2—H2	121.7 (10)	C11—C10—H10	120.9 (11)
C2—C3—C4	121.39 (15)	C9—C10—H10	119.3 (11)
C2—C3—H3	120.3 (12)	C12—C11—C10	120.43 (15)
C4—C3—H3	118.3 (12)	C12—C11—H11	121.9 (12)
C5—C4—C3	117.96 (14)	C10—C11—H11	117.7 (12)
C5—C4—C14	121.49 (17)	C11—C12—C13	120.19 (16)
C3—C4—C14	120.54 (18)	C11—C12—H12	122.5 (12)
C4—C5—C6	121.57 (15)	C13—C12—H12	117.3 (12)
C4—C5—H5	117.8 (11)	C12—C13—C8	119.63 (16)
C6—C5—H5	120.6 (11)	C12—C13—H13	121.6 (11)
C1—C6—C5	118.99 (15)	C8—C13—H13	118.8 (11)
C1—C6—H6	121.0 (11)	C4—C14—H14A	109.5
C5—C6—H6	120.0 (11)	C4—C14—H14B	109.5
O2—C7—O1	122.91 (13)	H14A—C14—H14B	109.5
O2—C7—C8	125.03 (13)	C4—C14—H14C	109.5
O1—C7—C8	112.01 (11)	H14A—C14—H14C	109.5
C9—C8—C13	119.73 (13)	H14B—C14—H14C	109.5
C9—C8—C7	122.33 (13)	C7—O1—C1	117.67 (10)
C6—C1—C2—C3	−0.6 (2)	O1—C7—C8—C13	−174.01 (13)
O1—C1—C2—C3	−177.45 (13)	C13—C8—C9—C10	−0.5 (2)
C1—C2—C3—C4	0.0 (3)	C7—C8—C9—C10	177.25 (14)
C2—C3—C4—C5	0.9 (2)	C8—C9—C10—C11	−0.4 (3)
C2—C3—C4—C14	179.86 (15)	C9—C10—C11—C12	0.7 (3)
C3—C4—C5—C6	−1.2 (2)	C10—C11—C12—C13	0.0 (3)
C14—C4—C5—C6	179.82 (16)	C11—C12—C13—C8	−0.9 (3)
C2—C1—C6—C5	0.3 (2)	C9—C8—C13—C12	1.2 (3)
O1—C1—C6—C5	177.24 (13)	C7—C8—C13—C12	−176.67 (14)
C4—C5—C6—C1	0.6 (3)	O2—C7—O1—C1	0.5 (2)
O2—C7—C8—C9	−169.30 (15)	C8—C7—O1—C1	−177.13 (11)
O1—C7—C8—C9	8.2 (2)	C2—C1—O1—C7	−70.34 (18)
O2—C7—C8—C13	8.5 (2)	C6—C1—O1—C7	112.73 (16)