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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034848/wn2173sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034848/wn2173Isup2.hkl
Contains datablock I

CCDC reference: 657809

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

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4
1 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 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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

Comment top

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 top

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).

Experimental top

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.

Refinement top

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]. Uiso(H) values were set equal to 1.2Ueq of the parent atom.

Structure description top

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).

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).

Computing details top

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 top
[Figure 1] 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.
[Figure 2] Fig. 2. Molecular packing of the title compound.
4-Methylphenyl benzoate top
Crystal data top
C14H12O2Z = 2
Mr = 212.24F(000) = 224
Triclinic, P1Dx = 1.205 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 8.1488 (9) ÅCell parameters from 25 reflections
b = 9.052 (1) Åθ = 6.2–25.2°
c = 9.299 (1) ŵ = 0.64 mm1
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) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
1903 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 66.9°, θmin = 5.1°
ω/2θ scansh = 98
Absorption correction: ψ scan
(North et al., 1968)
k = 1010
Tmin = 0.671, Tmax = 0.773l = 1111
3995 measured reflections3 standard reflections every 120 min
2082 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0629P)2 + 0.0783P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.003
2082 reflectionsΔρmax = 0.15 e Å3
174 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.173 (9)
Crystal data top
C14H12O2γ = 66.87 (1)°
Mr = 212.24V = 585.08 (11) Å3
Triclinic, P1Z = 2
a = 8.1488 (9) ÅCu Kα radiation
b = 9.052 (1) ŵ = 0.64 mm1
c = 9.299 (1) ÅT = 299 K
α = 76.99 (2)°0.60 × 0.48 × 0.40 mm
β = 68.73 (1)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1903 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.049
Tmin = 0.671, Tmax = 0.7733 standard reflections every 120 min
3995 measured reflections intensity decay: none
2082 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.15 e Å3
2082 reflectionsΔρmin = 0.24 e Å3
174 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
xyzUiso*/Ueq
C10.31783 (19)0.13239 (16)0.74315 (17)0.0559 (4)
C20.3400 (2)0.14401 (19)0.87892 (18)0.0641 (4)
H20.275 (2)0.092 (2)0.978 (2)0.077*
C30.4548 (2)0.2249 (2)0.8743 (2)0.0678 (5)
H30.476 (3)0.230 (2)0.965 (2)0.081*
C40.5471 (2)0.29397 (17)0.7360 (2)0.0664 (5)
C50.5191 (2)0.28167 (19)0.6023 (2)0.0714 (5)
H50.591 (3)0.328 (2)0.501 (2)0.086*
C60.4059 (2)0.20075 (19)0.60421 (19)0.0657 (4)
H60.385 (2)0.197 (2)0.512 (2)0.079*
C70.24839 (19)0.10521 (17)0.77574 (17)0.0554 (4)
C80.11334 (17)0.16976 (16)0.76323 (15)0.0513 (4)
C90.0320 (2)0.07552 (19)0.70380 (18)0.0586 (4)
H90.051 (2)0.035 (2)0.6694 (19)0.070*
C100.1494 (2)0.1426 (2)0.6884 (2)0.0717 (5)
H100.259 (3)0.071 (2)0.651 (2)0.086*
C110.1205 (3)0.3043 (2)0.7315 (2)0.0759 (5)
H110.202 (3)0.347 (2)0.718 (2)0.091*
C120.0232 (3)0.3988 (2)0.7912 (2)0.0769 (5)
H120.049 (3)0.513 (3)0.821 (2)0.092*
C130.1401 (2)0.33226 (19)0.8085 (2)0.0665 (4)
H130.241 (3)0.397 (2)0.852 (2)0.080*
C140.6715 (3)0.3822 (2)0.7336 (3)0.0987 (7)
H14A0.74060.32550.80560.118*
H14B0.59570.48940.76240.118*
H14C0.75730.38780.63110.118*
O10.19668 (14)0.05681 (12)0.74249 (14)0.0658 (4)
O20.39043 (16)0.18510 (13)0.80612 (16)0.0797 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0542 (8)0.0488 (8)0.0726 (9)0.0214 (6)0.0256 (6)0.0032 (6)
C20.0688 (9)0.0665 (10)0.0645 (9)0.0329 (8)0.0210 (7)0.0014 (7)
C30.0751 (10)0.0653 (10)0.0781 (10)0.0277 (8)0.0346 (8)0.0101 (8)
C40.0583 (8)0.0481 (8)0.0975 (12)0.0215 (7)0.0233 (8)0.0108 (7)
C50.0809 (11)0.0580 (9)0.0749 (10)0.0359 (8)0.0124 (8)0.0026 (7)
C60.0837 (11)0.0579 (9)0.0645 (9)0.0316 (8)0.0279 (8)0.0004 (7)
C70.0514 (7)0.0518 (8)0.0671 (9)0.0184 (6)0.0232 (6)0.0034 (6)
C80.0475 (7)0.0504 (8)0.0579 (8)0.0201 (6)0.0150 (6)0.0042 (6)
C90.0587 (8)0.0540 (8)0.0702 (9)0.0243 (7)0.0262 (7)0.0008 (6)
C100.0687 (10)0.0750 (11)0.0891 (11)0.0327 (8)0.0387 (8)0.0016 (8)
C110.0757 (11)0.0762 (11)0.0965 (13)0.0438 (9)0.0292 (9)0.0095 (9)
C120.0784 (11)0.0546 (9)0.1036 (13)0.0337 (8)0.0254 (9)0.0026 (8)
C130.0612 (9)0.0531 (9)0.0868 (11)0.0214 (7)0.0269 (8)0.0009 (7)
C140.0816 (12)0.0713 (12)0.161 (2)0.0391 (10)0.0371 (12)0.0209 (12)
O10.0635 (6)0.0525 (6)0.0964 (8)0.0260 (5)0.0406 (6)0.0030 (5)
O20.0681 (7)0.0609 (7)0.1268 (11)0.0191 (5)0.0553 (7)0.0029 (6)
Geometric parameters (Å, º) top
C1—C21.370 (2)C8—C91.380 (2)
C1—C61.372 (2)C8—C131.387 (2)
C1—O11.4070 (16)C9—C101.378 (2)
C2—C31.382 (2)C9—H90.947 (18)
C2—H20.996 (18)C10—C111.375 (3)
C3—C41.384 (2)C10—H101.01 (2)
C3—H30.93 (2)C11—C121.372 (3)
C4—C51.378 (2)C11—H110.94 (2)
C4—C141.509 (2)C12—C131.380 (2)
C5—C61.379 (2)C12—H120.97 (2)
C5—H51.011 (19)C13—H130.97 (2)
C6—H60.940 (19)C14—H14A0.9600
C7—O21.1958 (17)C14—H14B0.9600
C7—O11.3524 (17)C14—H14C0.9600
C7—C81.4814 (18)
C2—C1—C6121.18 (14)C13—C8—C7117.90 (13)
C2—C1—O1121.05 (13)C10—C9—C8120.23 (15)
C6—C1—O1117.70 (13)C10—C9—H9118.6 (10)
C1—C2—C3118.91 (15)C8—C9—H9121.1 (10)
C1—C2—H2119.4 (10)C11—C10—C9119.77 (16)
C3—C2—H2121.7 (10)C11—C10—H10120.9 (11)
C2—C3—C4121.39 (15)C9—C10—H10119.3 (11)
C2—C3—H3120.3 (12)C12—C11—C10120.43 (15)
C4—C3—H3118.3 (12)C12—C11—H11121.9 (12)
C5—C4—C3117.96 (14)C10—C11—H11117.7 (12)
C5—C4—C14121.49 (17)C11—C12—C13120.19 (16)
C3—C4—C14120.54 (18)C11—C12—H12122.5 (12)
C4—C5—C6121.57 (15)C13—C12—H12117.3 (12)
C4—C5—H5117.8 (11)C12—C13—C8119.63 (16)
C6—C5—H5120.6 (11)C12—C13—H13121.6 (11)
C1—C6—C5118.99 (15)C8—C13—H13118.8 (11)
C1—C6—H6121.0 (11)C4—C14—H14A109.5
C5—C6—H6120.0 (11)C4—C14—H14B109.5
O2—C7—O1122.91 (13)H14A—C14—H14B109.5
O2—C7—C8125.03 (13)C4—C14—H14C109.5
O1—C7—C8112.01 (11)H14A—C14—H14C109.5
C9—C8—C13119.73 (13)H14B—C14—H14C109.5
C9—C8—C7122.33 (13)C7—O1—C1117.67 (10)
C6—C1—C2—C30.6 (2)O1—C7—C8—C13174.01 (13)
O1—C1—C2—C3177.45 (13)C13—C8—C9—C100.5 (2)
C1—C2—C3—C40.0 (3)C7—C8—C9—C10177.25 (14)
C2—C3—C4—C50.9 (2)C8—C9—C10—C110.4 (3)
C2—C3—C4—C14179.86 (15)C9—C10—C11—C120.7 (3)
C3—C4—C5—C61.2 (2)C10—C11—C12—C130.0 (3)
C14—C4—C5—C6179.82 (16)C11—C12—C13—C80.9 (3)
C2—C1—C6—C50.3 (2)C9—C8—C13—C121.2 (3)
O1—C1—C6—C5177.24 (13)C7—C8—C13—C12176.67 (14)
C4—C5—C6—C10.6 (3)O2—C7—O1—C10.5 (2)
O2—C7—C8—C9169.30 (15)C8—C7—O1—C1177.13 (11)
O1—C7—C8—C98.2 (2)C2—C1—O1—C770.34 (18)
O2—C7—C8—C138.5 (2)C6—C1—O1—C7112.73 (16)

Experimental details

Crystal data
Chemical formulaC14H12O2
Mr212.24
Crystal system, space groupTriclinic, P1
Temperature (K)299
a, b, c (Å)8.1488 (9), 9.052 (1), 9.299 (1)
α, β, γ (°)76.99 (2), 68.73 (1), 66.87 (1)
V3)585.08 (11)
Z2
Radiation typeCu Kα
µ (mm1)0.64
Crystal size (mm)0.60 × 0.48 × 0.40
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.671, 0.773
No. of measured, independent and
observed [I > 2σ(I)] reflections
3995, 2082, 1903
Rint0.049
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.142, 1.06
No. of reflections2082
No. of parameters174
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.24

Computer programs: CAD-4-PC Software (Enraf–Nonius, 1996), CAD-4-PC Software, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

 

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