Phenyl 4-methyl-benzoate.

The structure of the title compound, C(14)H(12)O(2), resembles those of phenyl benzoate and 4-methyl-phenyl 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 inter-planar 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 = 212.24

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.145

S = 1.03

2138 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction , 2009 ▶); 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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039361/om2279Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H12O2	F(000) = 448
Mr = 212.24	Dx = 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

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

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(Fo2) + (0.0889P)2 + 0.0575P] where P = (Fo2 + 2Fc2)/3
2138 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)