Phenyl 4-methyl­benzoate

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Suchetan, P.A.; Fuess, H.

doi:10.1107/S1600536809039361

organic compounds

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Volume 65| Part 11| November 2009| Page o2620

https://doi.org/10.1107/S1600536809039361

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Phenyl 4-methylbenzoate

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b P. A. Suchetan ^a and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 15 September 2009; accepted 28 September 2009; online 3 October 2009)

The structure of the title compound, C₁₄H₁₂O₂, resembles those of phenyl benzoate and 4-methylphenyl benzoate, with similar bond parameters. The two aromatic rings make a dihedral angle of 76.0 (1)°. The plane of the central —C(=O)—O— group is twisted by 9.4 (2)° out of the plane of the benzoyl ring, and by 83.3 (1)° out of the plane of the phenyl ring. The crystal structure exhibits weak parallel stacking of the benzoyl rings, with an interplanar distance of 3.65 Å and an offset of 1.84 Å. The methyl group shows orientational disorder.

Related literature

For preparation of the compound, see: Nayak & Gowda (2009 ). For background to our study of the effects of substituents on the crystal structures of aryl benzoates and for related structures, see: Gowda et al. (2007a ,b , 2008 ). For phenyl benzoate, see: Adams & Morsi (1976 );

Experimental

Crystal data

C₁₄H₁₂O₂
M_r = 212.24
Monoclinic, P 2₁ /c
a = 12.3440 (4) Å
b = 8.1332 (2) Å
c = 12.1545 (4) Å
β = 110.911 (4)°
V = 1139.89 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.52 × 0.46 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.96, T_max = 0.98
20946 measured reflections
2138 independent reflections
1468 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.145
S = 1.03
2138 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction , 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809039361/om2279sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039361/om2279Isup2.hkl

checkCIF report

Comment top

In the present work, as a part of the study of the substituent effects on the crystal structures of aryl benzoates (Gowda et al., 2007a, b; 2008), the structure of phenyl-4-methylbenzoate (I) has been determined. The structure of (I) (Fig. 1) is similar to those of phenyl benzoate (II) (Adams & Morsi, 1976), 4-methylphenyl benzoate (III) (Gowda et al., 2007b), 4-methylphenyl 2-methylbenzoate (IV) (Gowda et al., 2008), 4-methylphenyl 4-methylbenzoate (V) (Gowda et al., 2007a) and other aryl benzoates. The two benzene rings make a dihedral angle of 76.0 (1)°, compared to the values of 55.7° for (II), 60.17 (7)° (III), 73.04 (8)° (IV) and 63.57 (5)° (V). The plane of the central –C(=O)–O– group in (I) is twisted 9.4 (2)° out of the plane of the benzoyl ring, and 83.3 (1)° out of the plane of the phenyl ring. The crystal structure exhibits weak parallel stacking of benzoyl rings, with interplanar distance of 3.65 Å and offset 1.84 Å. In the crystal structure, there are no classical hydrogen bonds. The molecules in the structure are packed into chains as viewed in the ac plane (Fig. 2).

Related literature top

For preparation of the compound, see: Nayak & Gowda (2009). For background to our study of the effects of substituent on the crystal structures of aryl benzoates and for related structures, see: Gowda et al. (2007a,b, 2008). For phenyl

benzoate, see: Adams & Morsi (1976);

Experimental top

The title compound was prepared according to a literature method (Nayak & Gowda, 2009). The purity of the compound was checked by determination of its melting point. It was characterized by infrared and NMR spectra (Nayak & Gowda, 2009). Colorless single crystals of the title compound were obtained by slow evaporation of its ethanol solution.

Structure description top

benzoate, see: Adams & Morsi (1976);

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction , 2009); data reduction: CrysAlis RED (Oxford Diffraction , 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound.

Phenyl 4-methylbenzoate top

Crystal data top

C₁₄H₁₂O₂	F(000) = 448
M_r = 212.24	D_x = 1.237 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9248 reflections
a = 12.3440 (4) Å	θ = 3.1–29.3°
b = 8.1332 (2) Å	µ = 0.08 mm⁻¹
c = 12.1545 (4) Å	T = 295 K
β = 110.911 (4)°	Block, colourless
V = 1139.89 (6) Å³	0.52 × 0.46 × 0.32 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector	2138 independent reflections
Graphite monochromator	1468 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.027
ω scans	θ_max = 25.6°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→15
T_min = 0.96, T_max = 0.98	k = −9→9
20946 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0889P)² + 0.0575P] where P = (F_o² + 2F_c²)/3
2138 reflections	(Δ/σ)_max = 0.001
146 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₄H₁₂O₂	V = 1139.89 (6) Å³
M_r = 212.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3440 (4) Å	µ = 0.08 mm⁻¹
b = 8.1332 (2) Å	T = 295 K
c = 12.1545 (4) Å	0.52 × 0.46 × 0.32 mm
β = 110.911 (4)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector	2138 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1468 reflections with I > 2σ(I)
T_min = 0.96, T_max = 0.98	R_int = 0.027
20946 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
2138 reflections	Δρ_min = −0.16 e Å⁻³
146 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	Occ. (<1)
C1	0.44050 (14)	0.7055 (2)	0.52718 (13)	0.0649 (4)
C2	0.42337 (16)	0.6054 (2)	0.60914 (16)	0.0826 (5)
H2	0.3509	0.559	0.5955	0.099*
C3	0.51407 (17)	0.5731 (2)	0.71233 (15)	0.0847 (6)
H3	0.503	0.5045	0.7686	0.102*
C4	0.61978 (16)	0.6415 (2)	0.73202 (15)	0.0809 (5)
H4	0.681	0.6201	0.8019	0.097*
C5	0.63602 (14)	0.7415 (2)	0.64933 (16)	0.0792 (5)
H5	0.7085	0.7882	0.6634	0.095*
C6	0.54637 (15)	0.7745 (2)	0.54505 (15)	0.0737 (5)
H6	0.5577	0.8419	0.4883	0.088*
C7	0.26747 (13)	0.84141 (18)	0.41132 (13)	0.0602 (4)
C8	0.17152 (12)	0.83643 (17)	0.29559 (12)	0.0558 (4)
C9	0.17601 (13)	0.74161 (18)	0.20301 (13)	0.0629 (4)
H9	0.2427	0.6822	0.2108	0.075*
C10	0.08196 (13)	0.73479 (19)	0.09922 (14)	0.0660 (4)
H10	0.0868	0.6716	0.0374	0.079*
C11	−0.01947 (13)	0.81929 (18)	0.08448 (13)	0.0633 (4)
C12	−0.02227 (14)	0.9156 (2)	0.17716 (15)	0.0718 (5)
H12	−0.0889	0.9754	0.1691	0.086*
C13	0.07132 (14)	0.92496 (18)	0.28101 (14)	0.0679 (4)
H13	0.0674	0.9911	0.3419	0.082*
C14	−0.12267 (15)	0.8048 (2)	−0.02748 (15)	0.0835 (5)
H14A	−0.1656	0.906	−0.042	0.125*	0.5
H14B	−0.1715	0.7167	−0.0203	0.125*	0.5
H14C	−0.097	0.7825	−0.0918	0.125*	0.5
H14D	−0.1924	0.8088	−0.0098	0.125*	0.5
H14E	−0.1192	0.7023	−0.0652	0.125*	0.5
H14F	−0.1224	0.8941	−0.0791	0.125*	0.5
O1	0.35063 (10)	0.72961 (15)	0.41782 (10)	0.0865 (4)
O2	0.27223 (9)	0.92969 (13)	0.49154 (9)	0.0758 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0612 (9)	0.0712 (10)	0.0534 (8)	0.0089 (8)	0.0095 (7)	−0.0108 (7)
C2	0.0734 (11)	0.0913 (12)	0.0790 (11)	−0.0181 (9)	0.0221 (9)	−0.0136 (10)
C3	0.1043 (15)	0.0767 (11)	0.0670 (11)	−0.0104 (10)	0.0230 (10)	0.0040 (8)
C4	0.0817 (12)	0.0714 (10)	0.0689 (11)	0.0066 (9)	0.0016 (9)	−0.0025 (8)
C5	0.0599 (10)	0.0815 (12)	0.0842 (12)	−0.0029 (8)	0.0110 (9)	−0.0022 (9)
C6	0.0729 (11)	0.0763 (11)	0.0705 (10)	0.0036 (9)	0.0238 (9)	0.0047 (8)
C7	0.0624 (9)	0.0576 (8)	0.0608 (9)	−0.0016 (7)	0.0222 (7)	−0.0014 (7)
C8	0.0562 (8)	0.0526 (8)	0.0581 (8)	−0.0029 (6)	0.0198 (7)	0.0001 (6)
C9	0.0572 (9)	0.0656 (9)	0.0629 (9)	0.0044 (7)	0.0178 (7)	−0.0038 (7)
C10	0.0642 (10)	0.0704 (10)	0.0597 (9)	−0.0018 (8)	0.0176 (8)	−0.0059 (7)
C11	0.0589 (9)	0.0602 (9)	0.0651 (9)	−0.0043 (7)	0.0153 (7)	0.0109 (7)
C12	0.0622 (10)	0.0683 (10)	0.0806 (11)	0.0143 (8)	0.0204 (8)	0.0094 (8)
C13	0.0733 (10)	0.0615 (9)	0.0697 (10)	0.0077 (8)	0.0264 (8)	−0.0012 (7)
C14	0.0669 (10)	0.0899 (12)	0.0778 (11)	−0.0072 (9)	0.0063 (9)	0.0131 (9)
O1	0.0739 (8)	0.1056 (9)	0.0623 (7)	0.0271 (7)	0.0024 (6)	−0.0195 (6)
O2	0.0821 (8)	0.0734 (7)	0.0660 (7)	0.0022 (6)	0.0193 (6)	−0.0148 (5)

Geometric parameters (Å, º) top

C1—C2	1.361 (2)	C8—C13	1.387 (2)
C1—C6	1.366 (2)	C9—C10	1.377 (2)
C1—O1	1.4082 (18)	C9—H9	0.93
C2—C3	1.376 (2)	C10—C11	1.383 (2)
C2—H2	0.93	C10—H10	0.93
C3—C4	1.359 (2)	C11—C12	1.383 (2)
C3—H3	0.93	C11—C14	1.500 (2)
C4—C5	1.362 (2)	C12—C13	1.376 (2)
C4—H4	0.93	C12—H12	0.93
C5—C6	1.379 (2)	C13—H13	0.93
C5—H5	0.93	C14—H14A	0.96
C6—H6	0.93	C14—H14B	0.96
C7—O2	1.1954 (16)	C14—H14C	0.96
C7—O1	1.3524 (18)	C14—H14D	0.96
C7—C8	1.481 (2)	C14—H14E	0.96
C8—C9	1.381 (2)	C14—H14F	0.96

C2—C1—C6	121.27 (15)	C8—C9—H9	119.9
C2—C1—O1	119.90 (15)	C9—C10—C11	121.80 (14)
C6—C1—O1	118.65 (15)	C9—C10—H10	119.1
C1—C2—C3	119.54 (17)	C11—C10—H10	119.1
C1—C2—H2	120.2	C12—C11—C10	117.44 (14)
C3—C2—H2	120.2	C12—C11—C14	121.56 (15)
C4—C3—C2	120.02 (17)	C10—C11—C14	121.00 (15)
C4—C3—H3	120	C13—C12—C11	121.45 (15)
C2—C3—H3	120	C13—C12—H12	119.3
C3—C4—C5	119.96 (16)	C11—C12—H12	119.3
C3—C4—H4	120	C12—C13—C8	120.48 (15)
C5—C4—H4	120	C12—C13—H13	119.8
C4—C5—C6	120.86 (17)	C8—C13—H13	119.8
C4—C5—H5	119.6	C11—C14—H14A	109.5
C6—C5—H5	119.6	C11—C14—H14B	109.5
C1—C6—C5	118.34 (16)	H14A—C14—H14B	109.5
C1—C6—H6	120.8	C11—C14—H14C	109.5
C5—C6—H6	120.8	H14A—C14—H14C	109.5
O2—C7—O1	122.75 (13)	H14B—C14—H14C	109.5
O2—C7—C8	125.51 (14)	C11—C14—H14D	109.5
O1—C7—C8	111.72 (12)	C11—C14—H14E	109.5
C9—C8—C13	118.62 (14)	H14D—C14—H14E	109.5
C9—C8—C7	122.54 (13)	C11—C14—H14F	109.5
C13—C8—C7	118.79 (13)	H14D—C14—H14F	109.5
C10—C9—C8	120.18 (14)	H14E—C14—H14F	109.5
C10—C9—H9	119.9	C7—O1—C1	118.32 (11)

C6—C1—C2—C3	0.3 (3)	C7—C8—C9—C10	176.63 (14)
O1—C1—C2—C3	175.36 (15)	C8—C9—C10—C11	−0.9 (2)
C1—C2—C3—C4	0.2 (3)	C9—C10—C11—C12	1.8 (2)
C2—C3—C4—C5	−0.3 (3)	C9—C10—C11—C14	−177.47 (14)
C3—C4—C5—C6	−0.1 (3)	C10—C11—C12—C13	−1.2 (2)
C2—C1—C6—C5	−0.7 (3)	C14—C11—C12—C13	178.09 (15)
O1—C1—C6—C5	−175.82 (14)	C11—C12—C13—C8	−0.3 (2)
C4—C5—C6—C1	0.6 (3)	C9—C8—C13—C12	1.3 (2)
O2—C7—C8—C9	174.22 (14)	C7—C8—C13—C12	−176.12 (14)
O1—C7—C8—C9	−7.1 (2)	O2—C7—O1—C1	6.3 (2)
O2—C7—C8—C13	−8.5 (2)	C8—C7—O1—C1	−172.34 (13)
O1—C7—C8—C13	170.12 (13)	C2—C1—O1—C7	82.15 (19)
C13—C8—C9—C10	−0.6 (2)	C6—C1—O1—C7	−102.63 (18)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂O₂
M_r	212.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.3440 (4), 8.1332 (2), 12.1545 (4)
β (°)	110.911 (4)
V (Å³)	1139.89 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.52 × 0.46 × 0.32

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.96, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	20946, 2138, 1468
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.145, 1.03
No. of reflections	2138
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction , 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Interreg IIIA, for financial support in the purchase of the diffractometer.

References

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