2,4-Dimethyl-phenyl benzoate.

The crystal structure of the title compound (24DMPBA), C(15)H(14)O(2), resembles those of 4-methyl-phenyl benzoate, 2,3-dimethyl-phenyl benzoate and other aryl benzoates, with similar bond parameters. The central -O-C-O- group in 24DMPBA makes dihedral angles of 85.81 (5) and 5.71 (13)°, respectively, with the benzoyl and phenyl rings, while the two aromatic rings form a dihedral angle of 80.25 (5)°. The mol-ecules are packed with their axes parallel to the a-axis direction.

Related literature

For related literature, see: Gowda et al. (2007 ▶, 2008 ▶); Nayak & Gowda (2008 ▶).

Experimental

Crystal data

C15H14O2

M = 226.26

Monoclinic,

a = 7.9813 (2) Å

b = 14.3260 (3) Å

c = 11.0932 (2) Å

β = 94.028 (2)°

V = 1265.26 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 (2) K

0.48 × 0.38 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.965, T max = 0.987

28657 measured reflections

2471 independent reflections

2056 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.134

S = 1.08

2471 reflections

156 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017480/ci2614sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017480/ci2614Isup2.hkl

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

C15H14O2	F000 = 480
Mr = 226.26	Dx = 1.188 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12993 reflections
a = 7.9813 (2) Å	θ = 3.2–29.3º
b = 14.3260 (3) Å	µ = 0.08 mm−1
c = 11.0932 (2) Å	T = 295 (2) K
β = 94.028 (2)º	Block, colourless
V = 1265.26 (5) Å3	0.48 × 0.38 × 0.21 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer	2471 independent reflections
Monochromator: graphite	2056 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.031
T = 295(2) K	θmax = 26.0º
ω scans with κ offsets	θmin = 5.9º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −9→9
Tmin = 0.965, Tmax = 0.987	k = −17→17
28657 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.2483P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2471 reflections	Δρmax = 0.16 e Å−3
156 parameters	Δρmin = −0.14 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)
O1	0.77410 (13)	0.30501 (7)	0.43628 (10)	0.0642 (3)
O2	0.56045 (16)	0.31504 (8)	0.29564 (11)	0.0795 (4)
C1	0.65706 (18)	0.35245 (10)	0.36678 (13)	0.0540 (4)
C2	0.66645 (18)	0.45392 (10)	0.38934 (13)	0.0529 (4)
C3	0.5646 (2)	0.51221 (12)	0.31812 (17)	0.0750 (5)
H3	0.4919	0.4871	0.2574	0.09*
C4	0.5690 (3)	0.60709 (14)	0.3358 (2)	0.0901 (6)
H4	0.5004	0.6458	0.2865	0.108*
C5	0.6720 (3)	0.64395 (12)	0.4237 (3)	0.0912 (7)
H5	0.6748	0.7082	0.4353	0.109*
C6	0.7731 (3)	0.58741 (14)	0.4966 (2)	0.0971 (7)
H6	0.8437	0.6134	0.5579	0.116*
C7	0.7711 (2)	0.49201 (12)	0.47963 (18)	0.0738 (5)
H7	0.8402	0.4537	0.5292	0.089*
C8	0.77716 (18)	0.20698 (10)	0.42443 (13)	0.0552 (4)
C9	0.8731 (2)	0.16674 (11)	0.34018 (14)	0.0623 (4)
C10	0.8778 (2)	0.06901 (12)	0.33938 (17)	0.0732 (5)
H10	0.9403	0.0392	0.2831	0.088*
C11	0.7940 (2)	0.01520 (12)	0.41818 (18)	0.0759 (5)
C12	0.7035 (2)	0.05916 (12)	0.50064 (19)	0.0786 (5)
H12	0.6473	0.0239	0.5555	0.094*
C13	0.6936 (2)	0.15527 (12)	0.50441 (16)	0.0682 (4)
H13	0.6306	0.1845	0.5609	0.082*
C14	0.9689 (3)	0.22412 (17)	0.2560 (2)	0.0964 (6)
H14A	0.9884	0.1881	0.1854	0.145*	0.56 (3)
H14B	1.0745	0.2423	0.2958	0.145*	0.56 (3)
H14C	0.9052	0.2789	0.2328	0.145*	0.56 (3)
H14D	0.9904	0.2847	0.2906	0.145*	0.44 (3)
H14E	0.9042	0.2305	0.1802	0.145*	0.44 (3)
H14F	1.0735	0.1939	0.2432	0.145*	0.44 (3)
C15	0.8030 (3)	−0.09032 (13)	0.4133 (3)	0.1179 (10)
H15A	0.771	−0.1159	0.4884	0.177*	0.67 (3)
H15B	0.9157	−0.1092	0.4002	0.177*	0.67 (3)
H15C	0.7279	−0.1128	0.3484	0.177*	0.67 (3)
H15D	0.8387	−0.1094	0.3362	0.177*	0.33 (3)
H15E	0.6941	−0.1161	0.4244	0.177*	0.33 (3)
H15F	0.8818	−0.1124	0.4762	0.177*	0.33 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0729 (7)	0.0412 (5)	0.0751 (7)	0.0067 (5)	−0.0183 (5)	−0.0071 (5)
O2	0.0873 (8)	0.0582 (7)	0.0878 (8)	0.0055 (6)	−0.0314 (7)	−0.0134 (6)
C1	0.0571 (8)	0.0488 (8)	0.0553 (8)	0.0039 (6)	−0.0018 (7)	−0.0026 (6)
C2	0.0542 (8)	0.0450 (7)	0.0601 (8)	0.0017 (6)	0.0072 (6)	0.0017 (6)
C3	0.0791 (11)	0.0585 (10)	0.0857 (12)	0.0119 (8)	−0.0066 (9)	0.0087 (8)
C4	0.0900 (14)	0.0574 (11)	0.1237 (17)	0.0170 (10)	0.0124 (13)	0.0235 (11)
C5	0.0875 (13)	0.0391 (9)	0.151 (2)	−0.0004 (9)	0.0357 (14)	0.0035 (11)
C6	0.1008 (15)	0.0578 (11)	0.1305 (18)	−0.0126 (10)	−0.0065 (13)	−0.0219 (11)
C7	0.0802 (11)	0.0480 (9)	0.0906 (12)	−0.0014 (8)	−0.0120 (9)	−0.0058 (8)
C8	0.0599 (9)	0.0420 (7)	0.0614 (9)	0.0049 (6)	−0.0113 (7)	−0.0057 (6)
C9	0.0636 (9)	0.0620 (9)	0.0598 (9)	0.0067 (7)	−0.0077 (7)	−0.0058 (7)
C10	0.0728 (11)	0.0665 (10)	0.0775 (11)	0.0210 (8)	−0.0152 (8)	−0.0246 (8)
C11	0.0760 (11)	0.0466 (9)	0.0998 (13)	0.0052 (7)	−0.0321 (9)	−0.0061 (8)
C12	0.0782 (12)	0.0592 (10)	0.0962 (13)	−0.0084 (8)	−0.0077 (9)	0.0118 (9)
C13	0.0691 (10)	0.0601 (10)	0.0752 (11)	0.0040 (8)	0.0039 (8)	−0.0023 (8)
C14	0.1010 (15)	0.1049 (16)	0.0852 (13)	0.0047 (12)	0.0189 (11)	0.0038 (12)
C15	0.1271 (19)	0.0463 (10)	0.170 (2)	0.0118 (10)	−0.0637 (18)	−0.0131 (12)

O1—C1	1.3519 (17)	C10—C11	1.374 (3)
O1—C8	1.4108 (17)	C10—H10	0.93
O2—C1	1.1913 (17)	C11—C12	1.359 (3)
C1—C2	1.476 (2)	C11—C15	1.514 (2)
C2—C7	1.371 (2)	C12—C13	1.380 (2)
C2—C3	1.376 (2)	C12—H12	0.93
C3—C4	1.373 (3)	C13—H13	0.93
C3—H3	0.93	C14—H14A	0.96
C4—C5	1.339 (3)	C14—H14B	0.96
C4—H4	0.93	C14—H14C	0.96
C5—C6	1.367 (3)	C14—H14D	0.96
C5—H5	0.93	C14—H14E	0.96
C6—C7	1.379 (3)	C14—H14F	0.96
C6—H6	0.93	C15—H15A	0.96
C7—H7	0.93	C15—H15B	0.96
C8—C13	1.365 (2)	C15—H15C	0.96
C8—C9	1.376 (2)	C15—H15D	0.96
C9—C10	1.401 (2)	C15—H15E	0.96
C9—C14	1.494 (3)	C15—H15F	0.96
C1—O1—C8	117.59 (11)	C9—C14—H14B	109.5
O2—C1—O1	122.74 (14)	H14A—C14—H14B	109.5
O2—C1—C2	125.32 (14)	C9—C14—H14C	109.5
O1—C1—C2	111.93 (12)	H14A—C14—H14C	109.5
C7—C2—C3	118.87 (15)	H14B—C14—H14C	109.5
C7—C2—C1	122.47 (14)	C9—C14—H14D	109.5
C3—C2—C1	118.65 (14)	H14A—C14—H14D	141.1
C4—C3—C2	120.70 (19)	H14B—C14—H14D	56.3
C4—C3—H3	119.7	H14C—C14—H14D	56.3
C2—C3—H3	119.7	C9—C14—H14E	109.5
C5—C4—C3	120.17 (19)	H14A—C14—H14E	56.3
C5—C4—H4	119.9	H14B—C14—H14E	141.1
C3—C4—H4	119.9	H14C—C14—H14E	56.3
C4—C5—C6	120.23 (17)	H14D—C14—H14E	109.5
C4—C5—H5	119.9	C9—C14—H14F	109.5
C6—C5—H5	119.9	H14A—C14—H14F	56.3
C5—C6—C7	120.4 (2)	H14B—C14—H14F	56.3
C5—C6—H6	119.8	H14C—C14—H14F	141.1
C7—C6—H6	119.8	H14D—C14—H14F	109.5
C2—C7—C6	119.64 (18)	H14E—C14—H14F	109.5
C2—C7—H7	120.2	C11—C15—H15A	109.5
C6—C7—H7	120.2	C11—C15—H15B	109.5
C13—C8—C9	122.33 (15)	H15A—C15—H15B	109.5
C13—C8—O1	117.84 (14)	C11—C15—H15C	109.5
C9—C8—O1	119.64 (14)	H15A—C15—H15C	109.5
C8—C9—C10	116.07 (16)	H15B—C15—H15C	109.5
C8—C9—C14	121.84 (16)	C11—C15—H15D	109.5
C10—C9—C14	122.09 (17)	H15A—C15—H15D	141.1
C11—C10—C9	122.86 (16)	H15B—C15—H15D	56.3
C11—C10—H10	118.6	H15C—C15—H15D	56.3
C9—C10—H10	118.6	C11—C15—H15E	109.5
C12—C11—C10	118.26 (16)	H15A—C15—H15E	56.3
C12—C11—C15	121.0 (2)	H15B—C15—H15E	141.1
C10—C11—C15	120.7 (2)	H15C—C15—H15E	56.3
C11—C12—C13	121.14 (18)	H15D—C15—H15E	109.5
C11—C12—H12	119.4	C11—C15—H15F	109.5
C13—C12—H12	119.4	H15A—C15—H15F	56.3
C8—C13—C12	119.34 (17)	H15B—C15—H15F	56.3
C8—C13—H13	120.3	H15C—C15—H15F	141.1
C12—C13—H13	120.3	H15D—C15—H15F	109.5
C9—C14—H14A	109.5	H15E—C15—H15F	109.5
C8—O1—C1—O2	−1.4 (2)	C1—O1—C8—C9	89.23 (17)
C8—O1—C1—C2	179.25 (12)	C13—C8—C9—C10	1.2 (2)
O2—C1—C2—C7	174.36 (17)	O1—C8—C9—C10	176.08 (13)
O1—C1—C2—C7	−6.4 (2)	C13—C8—C9—C14	−177.81 (16)
O2—C1—C2—C3	−4.7 (2)	O1—C8—C9—C14	−2.9 (2)
O1—C1—C2—C3	174.61 (14)	C8—C9—C10—C11	−0.7 (2)
C7—C2—C3—C4	0.9 (3)	C14—C9—C10—C11	178.30 (17)
C1—C2—C3—C4	−179.98 (17)	C9—C10—C11—C12	−0.3 (3)
C2—C3—C4—C5	−0.6 (3)	C9—C10—C11—C15	179.91 (16)
C3—C4—C5—C6	−0.1 (3)	C10—C11—C12—C13	0.9 (3)
C4—C5—C6—C7	0.5 (3)	C15—C11—C12—C13	−179.29 (17)
C3—C2—C7—C6	−0.5 (3)	C9—C8—C13—C12	−0.7 (2)
C1—C2—C7—C6	−179.57 (18)	O1—C8—C13—C12	−175.61 (14)
C5—C6—C7—C2	−0.2 (3)	C11—C12—C13—C8	−0.5 (3)
C1—O1—C8—C13	−95.67 (17)