4-Methyl­phenyl 4-methyl­benzoate

The structure of the title compound, C₁₅H₁₄O₂, is similar to that of phenyl benzoate and 4-methyl­phenyl benzoate, with somewhat different bond parameters. The dihedral angle between the two aromatic rings is 63.57 (5)°.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.144
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
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

As part of a study of substituent effects on the structures of chemically and industrially significant compounds (Gowda et al., 2007a, Gowda et al., 2007b; Gowda, Kozisek et al., 2007; Gowda, Foro, Nayak & Fuess, 2007), in the present work, the structure of 4-methylphenyl 4-methylbenzoate (4MeP4MeBA) has been determined. The structure of 4MeP4MeBA (Fig. 1) resembles that of phenyl benzoate (PBA) (Adams & Morsi, 1976) and 4-methylphenyl benzoate (4MePBA) (Gowda, Foro, Nayak & Fuess, 2007). The bond parameters in 4MeP4MeBA are similar to those in PBA, 4MePBA and other benzoates (Gowda et al., 2007a, b). The molecules in the title compound are packed in to chains in the ac plane (Fig. 2).

Related literature

For related literature, see: Adams & Morsi (1976); Gowda et al. (2007a,b); Gowda, Foro, Nayak & Fuess (2007); Gowda, Kozisek, Svoboda & Fuess (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 H atoms of the methyl groups were positioned with idealized geometry using a riding model with C—H = 0.96 Å. The other H atoms were located in difference map and their positions refined [C—H = 0.94 (2)–0.99 (2) Å]. All H atoms were refined with isotropic displacement parameters set to 1.2 times of the U_eq of the parent atom.

Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software (Enraf–Nonius, 1996); 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 (Sheldrick, 1997).

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 4-methylbenzoate

Crystal data

C15H14O2	F(000) = 480
Mr = 226.26	Dx = 1.219 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 6.113 (1) Å	θ = 3.4–22.4°
b = 7.639 (1) Å	µ = 0.64 mm^−1
c = 26.510 (3) Å	T = 299 K
β = 95.42 (1)°	Prism, colourless
V = 1232.4 (3) Å^3	0.53 × 0.33 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	1858 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 66.9°, θmin = 3.4°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = −9→4
Tmin = 0.782, Tmax = 0.934	l = −31→31
3680 measured reflections	3 standard reflections every 120 min
2202 independent reflections	intensity decay: 1.0%

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0792P)^2 + 0.2337P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2202 reflections	Δρmax = 0.19 e Å^−3
179 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (10)

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	0.6081 (3)	0.8160 (2)	0.12177 (6)	0.0558 (4)
C2	0.7010 (3)	0.7320 (3)	0.08374 (7)	0.0662 (5)
H2	0.846 (3)	0.682 (3)	0.0905 (7)	0.079*
C3	0.5881 (3)	0.7227 (3)	0.03619 (7)	0.0666 (5)
H3	0.655 (3)	0.661 (3)	0.0092 (7)	0.080*
C4	0.3811 (3)	0.7961 (2)	0.02643 (6)	0.0588 (4)
C5	0.2931 (3)	0.8796 (2)	0.06581 (7)	0.0638 (5)
H5	0.145 (3)	0.932 (3)	0.0617 (7)	0.077*
C6	0.4036 (3)	0.8908 (2)	0.11347 (7)	0.0628 (4)
H6	0.345 (3)	0.951 (3)	0.1414 (8)	0.075*
C7	0.8771 (2)	0.93572 (19)	0.18165 (6)	0.0494 (4)
C8	0.9683 (2)	0.92623 (18)	0.23520 (5)	0.0472 (4)
C9	0.8641 (3)	0.8382 (2)	0.27175 (6)	0.0549 (4)
H9	0.724 (3)	0.782 (2)	0.2616 (6)	0.066*
C10	0.9581 (3)	0.8317 (2)	0.32113 (6)	0.0575 (4)
H10	0.888 (3)	0.768 (3)	0.3452 (7)	0.069*
C11	1.1604 (3)	0.90905 (19)	0.33506 (6)	0.0525 (4)
C12	1.2617 (3)	0.9984 (2)	0.29839 (6)	0.0593 (4)
H12	1.408 (3)	1.054 (2)	0.3062 (7)	0.071*
C13	1.1678 (3)	1.0089 (2)	0.24920 (6)	0.0564 (4)
H13	1.236 (3)	1.078 (2)	0.2247 (7)	0.068*
C14	0.2563 (4)	0.7841 (3)	−0.02516 (7)	0.0833 (6)
H14A	0.2982	0.6794	−0.0418	0.100*
H14B	0.2896	0.8842	−0.0450	0.100*
H14C	0.1014	0.7812	−0.0217	0.100*
C15	1.2671 (3)	0.8948 (3)	0.38833 (6)	0.0701 (5)
H15A	1.2080	0.7957	0.4047	0.084*
H15B	1.2387	0.9994	0.4067	0.084*
H15C	1.4228	0.8802	0.3876	0.084*
O1	0.7127 (2)	0.81850 (16)	0.17135 (4)	0.0690 (4)
O2	0.93656 (18)	1.03321 (16)	0.15041 (4)	0.0649 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0533 (8)	0.0618 (9)	0.0501 (8)	−0.0079 (7)	−0.0077 (6)	0.0050 (7)
C2	0.0534 (9)	0.0750 (11)	0.0677 (10)	0.0127 (8)	−0.0065 (8)	0.0021 (9)
C3	0.0653 (10)	0.0754 (11)	0.0579 (9)	0.0100 (9)	0.0001 (8)	−0.0063 (8)
C4	0.0597 (9)	0.0563 (9)	0.0573 (9)	−0.0027 (7)	−0.0110 (7)	0.0052 (7)
C5	0.0487 (8)	0.0677 (10)	0.0725 (10)	0.0060 (8)	−0.0079 (7)	0.0006 (8)
C6	0.0550 (9)	0.0720 (11)	0.0607 (9)	−0.0004 (8)	0.0027 (7)	−0.0072 (8)
C7	0.0431 (7)	0.0513 (8)	0.0531 (8)	0.0035 (6)	0.0015 (6)	0.0013 (6)
C8	0.0450 (7)	0.0463 (8)	0.0496 (8)	0.0024 (6)	0.0005 (6)	0.0001 (6)
C9	0.0474 (8)	0.0592 (9)	0.0568 (9)	−0.0078 (7)	−0.0013 (6)	0.0032 (7)
C10	0.0587 (9)	0.0621 (9)	0.0513 (8)	−0.0076 (7)	0.0030 (7)	0.0053 (7)
C11	0.0576 (8)	0.0479 (8)	0.0504 (8)	0.0023 (7)	−0.0029 (7)	−0.0049 (6)
C12	0.0526 (9)	0.0637 (10)	0.0599 (9)	−0.0120 (7)	−0.0038 (7)	−0.0052 (8)
C13	0.0535 (8)	0.0616 (9)	0.0537 (9)	−0.0110 (7)	0.0040 (7)	0.0018 (7)
C14	0.0895 (14)	0.0883 (14)	0.0659 (11)	−0.0005 (11)	−0.0254 (10)	0.0036 (10)
C15	0.0791 (12)	0.0728 (11)	0.0552 (9)	−0.0035 (9)	−0.0110 (8)	−0.0034 (8)
O1	0.0707 (7)	0.0798 (8)	0.0527 (7)	−0.0230 (6)	−0.0148 (5)	0.0114 (6)
O2	0.0622 (7)	0.0767 (8)	0.0550 (7)	−0.0098 (6)	0.0003 (5)	0.0121 (6)

Geometric parameters (Å, º)

C1—C2	1.364 (2)	C8—C13	1.392 (2)
C1—C6	1.374 (2)	C9—C10	1.380 (2)
C1—O1	1.4062 (18)	C9—H9	0.971 (18)
C2—C3	1.381 (2)	C10—C11	1.389 (2)
C2—H2	0.968 (19)	C10—H10	0.935 (18)
C3—C4	1.386 (2)	C11—C12	1.381 (2)
C3—H3	0.98 (2)	C11—C15	1.503 (2)
C4—C5	1.375 (2)	C12—C13	1.377 (2)
C4—C14	1.505 (2)	C12—H12	0.994 (19)
C5—C6	1.378 (2)	C13—H13	0.962 (18)
C5—H5	0.99 (2)	C14—H14A	0.9600
C6—H6	0.97 (2)	C14—H14B	0.9600
C7—O2	1.1957 (18)	C14—H14C	0.9600
C7—O1	1.3547 (18)	C15—H15A	0.9600
C7—C8	1.477 (2)	C15—H15B	0.9600
C8—C9	1.383 (2)	C15—H15C	0.9600
C2—C1—C6	120.92 (15)	C8—C9—H9	118.1 (10)
C2—C1—O1	120.89 (15)	C9—C10—C11	121.17 (15)
C6—C1—O1	118.06 (15)	C9—C10—H10	119.2 (11)
C1—C2—C3	119.48 (16)	C11—C10—H10	119.5 (11)
C1—C2—H2	119.2 (11)	C12—C11—C10	118.06 (14)
C3—C2—H2	121.3 (11)	C12—C11—C15	120.90 (15)
C2—C3—C4	121.23 (17)	C10—C11—C15	121.04 (15)
C2—C3—H3	119.0 (12)	C13—C12—C11	121.40 (15)
C4—C3—H3	119.8 (12)	C13—C12—H12	117.3 (11)
C5—C4—C3	117.49 (15)	C11—C12—H12	121.2 (11)
C5—C4—C14	121.14 (16)	C12—C13—C8	120.15 (15)
C3—C4—C14	121.37 (17)	C12—C13—H13	120.2 (11)
C4—C5—C6	122.13 (16)	C8—C13—H13	119.6 (11)
C4—C5—H5	121.6 (11)	C4—C14—H14A	109.5
C6—C5—H5	116.3 (11)	C4—C14—H14B	109.5
C1—C6—C5	118.75 (16)	H14A—C14—H14B	109.5
C1—C6—H6	118.3 (12)	C4—C14—H14C	109.5
C5—C6—H6	122.9 (12)	H14A—C14—H14C	109.5
O2—C7—O1	122.71 (14)	H14B—C14—H14C	109.5
O2—C7—C8	125.78 (14)	C11—C15—H15A	109.5
O1—C7—C8	111.52 (12)	C11—C15—H15B	109.5
C9—C8—C13	118.92 (14)	H15A—C15—H15B	109.5
C9—C8—C7	122.70 (13)	C11—C15—H15C	109.5
C13—C8—C7	118.38 (13)	H15A—C15—H15C	109.5
C10—C9—C8	120.25 (14)	H15B—C15—H15C	109.5
C10—C9—H9	121.6 (10)	C7—O1—C1	117.42 (12)
C6—C1—C2—C3	0.2 (3)	C13—C8—C9—C10	−0.5 (2)
O1—C1—C2—C3	176.04 (16)	C7—C8—C9—C10	179.20 (14)
C1—C2—C3—C4	−0.5 (3)	C8—C9—C10—C11	−1.6 (3)
C2—C3—C4—C5	0.4 (3)	C9—C10—C11—C12	2.3 (2)
C2—C3—C4—C14	−179.18 (18)	C9—C10—C11—C15	−177.20 (16)
C3—C4—C5—C6	−0.2 (3)	C10—C11—C12—C13	−1.0 (2)
C14—C4—C5—C6	179.43 (17)	C15—C11—C12—C13	178.51 (16)
C2—C1—C6—C5	0.0 (3)	C11—C12—C13—C8	−1.1 (3)
O1—C1—C6—C5	−175.92 (15)	C9—C8—C13—C12	1.8 (2)
C4—C5—C6—C1	0.0 (3)	C7—C8—C13—C12	−177.92 (14)
O2—C7—C8—C9	166.01 (15)	O2—C7—O1—C1	−1.0 (2)
O1—C7—C8—C9	−13.8 (2)	C8—C7—O1—C1	178.81 (13)
O2—C7—C8—C13	−14.3 (2)	C2—C1—O1—C7	80.2 (2)
O1—C7—C8—C13	165.92 (13)	C6—C1—O1—C7	−103.85 (18)