3-Methyl­phenyl benzoate

The structure of the title compound, C₁₄H₁₂O₂, resembles that of phenyl benzoate and 4-methyl­phenyl benzoate, with similar geometric parameters. The dihedral angle between the phenyl and benzoyl rings is 79.61 (6)°, compared to values of 55.7° for phenyl benzoate and 60.17 (7)° for 4-methyl­phenyl benzoate. The mol­ecules in the title compound are packed with the methyl­phenyl and the benzoyl rings nearly orthogonal to each other.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.131
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

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Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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., 2007a, b; Gowda, Kozisek et al., 2007), the structure of 3-methylphenyl benzoate (3MePBA) has been determined. The structure of 3MePBA (Fig. 1) is similar to that of phenyl benzoate (PBA) (Adams & Morsi, 1976) and 4-methylphenyl benzoate (4MePBA) (Gowda, Foro et al., 2007b). The bond parameters in 3MePBA are similar to those in PBA, 4MePBA and other benzoates. The molecules in the title compound are packed with the methylphenyl and the benzoyl rings nearly orthoganal to each other (Fig. 2).

Related literature

For related literature, see: Adams & Morsi (1976); Gowda, Kozisek et al. (2007); Gowda et al. (2007a, 2007b); 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 H atoms of the methyl group were positioned with idealized geometry and included in further refinement using a riding model approximation [C—H = 0.96 Å, U_iso(H) = 1.2U_eq(C)]. In addition, the methyl group was allowed to rotate but not to tip. All other H atoms were located in the difference map, and their positional parameters were refined, whereas their isotropic displacement parameters were set to 1.2 U_eq of the parent atom.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; 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 with hydrogen bonding shown as dashed lines.

3-Methylphenyl benzoate

Crystal data

C14H12O2	F(000) = 448
Mr = 212.24	Dx = 1.226 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2877 reflections
a = 9.530 (1) Å	θ = 2.1–25.2°
b = 10.676 (1) Å	µ = 0.08 mm^−1
c = 11.654 (2) Å	T = 299 K
β = 104.04 (1)°	Prism, colourless
V = 1150.3 (3) Å^3	0.50 × 0.50 × 0.40 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with a Sapphire CCD detector	2341 independent reflections
Radiation source: fine-focus sealed tube	1624 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 4.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −11→11
Tmin = 0.951, Tmax = 0.977	k = −13→13
8434 measured reflections	l = −14→14

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.053P)^2 + 0.3191P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.004
2341 reflections	Δρmax = 0.17 e Å^−3
174 parameters	Δρmin = −0.16 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: 0.039 (4)

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	0.26886 (17)	0.15483 (17)	0.03031 (15)	0.0540 (4)
C2	0.3452 (2)	0.14859 (19)	−0.05466 (17)	0.0602 (5)
H2	0.371 (2)	0.071 (2)	−0.0830 (18)	0.072*
C3	0.3866 (2)	0.2592 (2)	−0.09759 (17)	0.0633 (5)
H3	0.442 (2)	0.2570 (18)	−0.156 (2)	0.076*
C4	0.3513 (2)	0.37200 (19)	−0.05653 (16)	0.0608 (5)
H4	0.382 (2)	0.450 (2)	−0.0862 (18)	0.073*
C5	0.2725 (2)	0.37878 (18)	0.02860 (16)	0.0616 (5)
C6	0.2318 (2)	0.26692 (19)	0.07217 (16)	0.0594 (5)
H6	0.175 (2)	0.2674 (18)	0.1315 (19)	0.071*
C7	0.31272 (17)	−0.01993 (16)	0.15799 (14)	0.0505 (4)
C8	0.24368 (17)	−0.12558 (15)	0.20569 (14)	0.0478 (4)
C9	0.09865 (19)	−0.15503 (18)	0.16453 (16)	0.0578 (5)
H9	0.040 (2)	−0.1072 (18)	0.1003 (18)	0.069*
C10	0.0395 (2)	−0.2517 (2)	0.21564 (19)	0.0673 (5)
H10	−0.062 (3)	−0.268 (2)	0.1874 (19)	0.081*
C11	0.1233 (2)	−0.3176 (2)	0.30867 (18)	0.0674 (5)
H11	0.080 (2)	−0.386 (2)	0.3449 (19)	0.081*
C12	0.2675 (2)	−0.28943 (19)	0.34923 (18)	0.0653 (5)
H12	0.324 (2)	−0.335 (2)	0.4132 (19)	0.078*
C13	0.3281 (2)	−0.19441 (17)	0.29812 (16)	0.0565 (4)
H13	0.429 (2)	−0.1738 (18)	0.3242 (17)	0.068*
C14	0.2329 (3)	0.5024 (2)	0.0733 (3)	0.0986 (8)
H14A	0.1898	0.5551	0.0074	0.118*
H14B	0.3183	0.5420	0.1198	0.118*
H14C	0.1652	0.4891	0.1211	0.118*
O1	0.21733 (13)	0.04446 (13)	0.07312 (12)	0.0681 (4)
O2	0.43703 (13)	0.00903 (13)	0.19029 (12)	0.0684 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0465 (9)	0.0572 (10)	0.0542 (9)	−0.0076 (8)	0.0044 (7)	0.0100 (8)
C2	0.0587 (11)	0.0589 (11)	0.0636 (11)	0.0005 (9)	0.0162 (8)	−0.0012 (9)
C3	0.0601 (11)	0.0763 (13)	0.0558 (10)	−0.0049 (9)	0.0185 (8)	0.0048 (9)
C4	0.0613 (11)	0.0616 (12)	0.0563 (10)	−0.0106 (9)	0.0078 (8)	0.0091 (9)
C5	0.0611 (11)	0.0608 (11)	0.0579 (10)	−0.0020 (9)	0.0047 (8)	−0.0047 (9)
C6	0.0562 (10)	0.0733 (13)	0.0495 (9)	−0.0033 (9)	0.0142 (8)	0.0013 (9)
C7	0.0463 (9)	0.0546 (10)	0.0500 (8)	0.0002 (7)	0.0105 (7)	−0.0024 (7)
C8	0.0486 (9)	0.0469 (9)	0.0482 (8)	0.0010 (7)	0.0124 (7)	−0.0036 (7)
C9	0.0509 (10)	0.0639 (11)	0.0570 (10)	−0.0022 (8)	0.0100 (8)	0.0073 (9)
C10	0.0558 (11)	0.0741 (13)	0.0720 (12)	−0.0120 (10)	0.0151 (9)	0.0039 (10)
C11	0.0773 (13)	0.0570 (11)	0.0702 (12)	−0.0080 (10)	0.0224 (10)	0.0068 (9)
C12	0.0734 (13)	0.0553 (11)	0.0628 (11)	0.0037 (9)	0.0078 (9)	0.0093 (9)
C13	0.0522 (10)	0.0534 (10)	0.0603 (10)	0.0022 (8)	0.0065 (8)	−0.0003 (8)
C14	0.114 (2)	0.0758 (16)	0.1066 (18)	0.0040 (14)	0.0288 (15)	−0.0192 (14)
O1	0.0533 (7)	0.0690 (8)	0.0754 (8)	−0.0119 (6)	0.0028 (6)	0.0228 (7)
O2	0.0478 (7)	0.0762 (9)	0.0781 (9)	−0.0065 (6)	0.0092 (6)	0.0115 (7)

Geometric parameters (Å, º)

C1—C2	1.365 (3)	C8—C9	1.385 (2)
C1—C6	1.371 (3)	C8—C13	1.388 (2)
C1—O1	1.413 (2)	C9—C10	1.379 (3)
C2—C3	1.377 (3)	C9—H9	0.97 (2)
C2—H2	0.95 (2)	C10—C11	1.374 (3)
C3—C4	1.368 (3)	C10—H10	0.96 (2)
C3—H3	0.96 (2)	C11—C12	1.374 (3)
C4—C5	1.383 (3)	C11—H11	0.98 (2)
C4—H4	0.97 (2)	C12—C13	1.373 (3)
C5—C6	1.389 (3)	C12—H12	0.94 (2)
C5—C14	1.500 (3)	C13—H13	0.96 (2)
C6—H6	0.98 (2)	C14—H14A	0.9600
C7—O2	1.1935 (19)	C14—H14B	0.9600
C7—O1	1.357 (2)	C14—H14C	0.9600
C7—C8	1.480 (2)
C2—C1—C6	121.98 (17)	C13—C8—C7	117.90 (15)
C2—C1—O1	120.48 (17)	C10—C9—C8	119.92 (17)
C6—C1—O1	117.43 (16)	C10—C9—H9	120.6 (11)
C1—C2—C3	118.14 (18)	C8—C9—H9	119.5 (11)
C1—C2—H2	121.4 (12)	C11—C10—C9	120.23 (19)
C3—C2—H2	120.5 (12)	C11—C10—H10	121.3 (13)
C4—C3—C2	120.76 (18)	C9—C10—H10	118.4 (13)
C4—C3—H3	119.7 (12)	C12—C11—C10	120.09 (19)
C2—C3—H3	119.5 (12)	C12—C11—H11	120.2 (12)
C3—C4—C5	121.29 (18)	C10—C11—H11	119.7 (12)
C3—C4—H4	120.4 (12)	C13—C12—C11	120.23 (18)
C5—C4—H4	118.3 (12)	C13—C12—H12	120.3 (13)
C4—C5—C6	117.74 (18)	C11—C12—H12	119.5 (13)
C4—C5—C14	121.39 (19)	C12—C13—C8	120.13 (17)
C6—C5—C14	120.87 (19)	C12—C13—H13	121.7 (12)
C1—C6—C5	120.09 (17)	C8—C13—H13	118.1 (12)
C1—C6—H6	119.5 (12)	C5—C14—H14A	109.5
C5—C6—H6	120.4 (12)	C5—C14—H14B	109.5
O2—C7—O1	122.47 (16)	H14A—C14—H14B	109.5
O2—C7—C8	125.20 (15)	C5—C14—H14C	109.5
O1—C7—C8	112.31 (13)	H14A—C14—H14C	109.5
C9—C8—C13	119.38 (16)	H14B—C14—H14C	109.5
C9—C8—C7	122.69 (15)	C7—O1—C1	116.81 (13)
C6—C1—C2—C3	0.7 (3)	O1—C7—C8—C13	−176.29 (15)
O1—C1—C2—C3	176.76 (15)	C13—C8—C9—C10	0.2 (3)
C1—C2—C3—C4	−0.4 (3)	C7—C8—C9—C10	−177.56 (17)
C2—C3—C4—C5	−0.3 (3)	C8—C9—C10—C11	1.1 (3)
C3—C4—C5—C6	0.7 (3)	C9—C10—C11—C12	−1.7 (3)
C3—C4—C5—C14	−179.64 (19)	C10—C11—C12—C13	0.8 (3)
C2—C1—C6—C5	−0.3 (3)	C11—C12—C13—C8	0.5 (3)
O1—C1—C6—C5	−176.50 (15)	C9—C8—C13—C12	−1.0 (3)
C4—C5—C6—C1	−0.4 (3)	C7—C8—C13—C12	176.86 (16)
C14—C5—C6—C1	179.97 (18)	O2—C7—O1—C1	−5.0 (3)
O2—C7—C8—C9	−179.88 (17)	C8—C7—O1—C1	173.70 (14)
O1—C7—C8—C9	1.5 (2)	C2—C1—O1—C7	82.1 (2)
O2—C7—C8—C13	2.3 (3)	C6—C1—O1—C7	−101.67 (18)