Crystal structure of 4-acetyl-phenyl 3-methyl-benzoate.

The planes of the aromatic rings of the title compound, C16H14O3, make a dihedral angle of 82.52 (8)°. The acetyl group and the phenyl ring make a dihedral angle of 1.65 (1)°. In the crystal, the molecules are linked by C-H⋯O interactions, generating C(7) chains along the a-axis direction.

Related literature

For the biological activity of aceto­phenone derivatives, see: Chung et al. (2003 ▶).

Experimental

Crystal data

C16H14O3

M = 254.27

Monoclinic,

a = 8.7167 (3) Å

b = 9.8521 (3) Å

c = 15.4938 (4) Å

β = 95.149 (2)°

V = 1325.20 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.974, T max = 0.983

12798 measured reflections

3303 independent reflections

2130 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.162

S = 1.00

3303 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814018923/bt6992sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018923/bt6992Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018923/bt6992Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018923/bt6992fig1.tif

The mol­ecular structure of the title compound, showing the atomic numbering and displacement ellipsoids drawn at 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S1600536814018923/bt6992fig2.tif

The crystal packing of the title compound viewed down the a axis. Inter­molecular hydrogen bonds are shown as dashed lines. H-atoms not involved in H-bonds have been excluded for clarity.

CCDC reference: 1020285

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H14O3	F(000) = 536
Mr = 254.27	Dx = 1.274 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3303 reflections
a = 8.7167 (3) Å	θ = 2.4–28.3°
b = 9.8521 (3) Å	µ = 0.09 mm−1
c = 15.4938 (4) Å	T = 293 K
β = 95.149 (2)°	Block, colourless
V = 1325.20 (7) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	3303 independent reflections
Radiation source: fine-focus sealed tube	2130 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→9
Tmin = 0.974, Tmax = 0.983	k = −10→13
12798 measured reflections	l = −20→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0803P)2 + 0.1756P] where P = (Fo2 + 2Fc2)/3
3303 reflections	(Δ/σ)max = 0.043
174 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.2306 (3)	1.0754 (3)	−0.43251 (12)	0.0957 (7)
H1A	0.3009	1.1250	−0.4649	0.144*
H1B	0.1793	1.1370	−0.3966	0.144*
H1C	0.1557	1.0305	−0.4718	0.144*
C2	0.31775 (19)	0.97205 (18)	−0.37669 (9)	0.0637 (4)
C3	0.4192 (2)	0.88402 (19)	−0.41068 (11)	0.0747 (5)
H3	0.4342	0.8893	−0.4693	0.090*
C4	0.4986 (2)	0.7889 (2)	−0.36009 (13)	0.0826 (6)
H4	0.5666	0.7306	−0.3845	0.099*
C5	0.4783 (2)	0.77929 (17)	−0.27263 (11)	0.0711 (5)
H5	0.5326	0.7151	−0.2381	0.085*
C6	0.37624 (16)	0.86609 (15)	−0.23730 (9)	0.0538 (4)
C7	0.29747 (17)	0.96191 (16)	−0.28903 (9)	0.0562 (4)
H7	0.2297	1.0207	−0.2648	0.067*
C8	0.35490 (18)	0.85016 (16)	−0.14433 (9)	0.0576 (4)
C9	0.21558 (18)	0.92477 (16)	−0.03042 (9)	0.0581 (4)
C10	0.10870 (19)	0.83096 (17)	−0.01086 (10)	0.0669 (4)
H10	0.0630	0.7740	−0.0536	0.080*
C11	0.06933 (19)	0.82189 (17)	0.07360 (11)	0.0655 (4)
H11	−0.0027	0.7578	0.0876	0.079*
C12	0.13591 (17)	0.90698 (15)	0.13718 (9)	0.0553 (4)
C13	0.24248 (19)	1.00229 (17)	0.11470 (10)	0.0621 (4)
H13	0.2874	1.0609	0.1567	0.075*
C14	0.28287 (19)	1.01129 (17)	0.03027 (10)	0.0642 (4)
H14	0.3545	1.0752	0.0154	0.077*
C15	0.0930 (2)	0.89341 (17)	0.22797 (11)	0.0662 (4)
C16	0.1621 (3)	0.9862 (2)	0.29564 (11)	0.0912 (6)
H16A	0.1261	0.9627	0.3505	0.137*
H16B	0.1329	1.0779	0.2811	0.137*
H16C	0.2723	0.9783	0.2993	0.137*
O1	0.00206 (19)	0.80739 (15)	0.24608 (9)	0.0967 (5)
O2	0.25094 (14)	0.93822 (12)	−0.11686 (6)	0.0694 (3)
O3	0.42165 (16)	0.77076 (15)	−0.09685 (7)	0.0882 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0939 (14)	0.1320 (18)	0.0614 (10)	0.0018 (13)	0.0082 (9)	0.0211 (11)
C2	0.0628 (9)	0.0782 (11)	0.0507 (8)	−0.0189 (8)	0.0079 (7)	−0.0029 (7)
C3	0.0875 (12)	0.0843 (12)	0.0551 (8)	−0.0229 (10)	0.0220 (8)	−0.0151 (8)
C4	0.0967 (14)	0.0730 (12)	0.0838 (12)	−0.0033 (10)	0.0388 (10)	−0.0202 (10)
C5	0.0796 (11)	0.0615 (10)	0.0747 (10)	0.0042 (8)	0.0199 (9)	−0.0054 (8)
C6	0.0544 (8)	0.0544 (8)	0.0533 (7)	−0.0079 (6)	0.0089 (6)	−0.0067 (6)
C7	0.0549 (8)	0.0630 (9)	0.0513 (7)	−0.0068 (7)	0.0082 (6)	−0.0048 (6)
C8	0.0596 (9)	0.0581 (8)	0.0555 (8)	0.0002 (7)	0.0080 (6)	0.0000 (7)
C9	0.0636 (9)	0.0639 (9)	0.0473 (7)	0.0127 (7)	0.0090 (6)	0.0038 (6)
C10	0.0697 (10)	0.0673 (10)	0.0635 (9)	−0.0004 (8)	0.0047 (8)	−0.0113 (7)
C11	0.0629 (9)	0.0638 (9)	0.0716 (9)	−0.0035 (7)	0.0164 (7)	−0.0027 (8)
C12	0.0558 (8)	0.0564 (8)	0.0550 (8)	0.0108 (6)	0.0115 (6)	0.0026 (6)
C13	0.0682 (9)	0.0672 (9)	0.0511 (7)	−0.0030 (8)	0.0066 (7)	−0.0032 (7)
C14	0.0692 (10)	0.0687 (10)	0.0556 (8)	−0.0057 (8)	0.0107 (7)	0.0051 (7)
C15	0.0742 (10)	0.0623 (9)	0.0652 (9)	0.0159 (8)	0.0240 (8)	0.0063 (7)
C16	0.1263 (17)	0.0948 (14)	0.0551 (9)	0.0026 (13)	0.0238 (10)	−0.0015 (9)
O1	0.1189 (11)	0.0866 (9)	0.0923 (9)	−0.0109 (8)	0.0523 (8)	0.0021 (7)
O2	0.0850 (8)	0.0765 (7)	0.0481 (5)	0.0207 (6)	0.0143 (5)	0.0048 (5)
O3	0.0999 (10)	0.0972 (9)	0.0702 (7)	0.0355 (8)	0.0226 (7)	0.0232 (7)

C1—C2	1.498 (3)	C9—C14	1.362 (2)
C1—H1A	0.9600	C9—C10	1.366 (2)
C1—H1B	0.9600	C9—O2	1.4071 (17)
C1—H1C	0.9600	C10—C11	1.385 (2)
C2—C3	1.377 (2)	C10—H10	0.9300
C2—C7	1.389 (2)	C11—C12	1.381 (2)
C3—C4	1.369 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.387 (2)
C4—C5	1.386 (2)	C12—C15	1.494 (2)
C4—H4	0.9300	C13—C14	1.388 (2)
C5—C6	1.382 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.381 (2)	C15—O1	1.210 (2)
C6—C8	1.477 (2)	C15—C16	1.478 (3)
C7—H7	0.9300	C16—H16A	0.9600
C8—O3	1.1895 (18)	C16—H16B	0.9600
C8—O2	1.3506 (18)	C16—H16C	0.9600
C2—C1—H1A	109.5	C14—C9—O2	118.72 (15)
C2—C1—H1B	109.5	C10—C9—O2	119.14 (14)
H1A—C1—H1B	109.5	C9—C10—C11	119.01 (15)
C2—C1—H1C	109.5	C9—C10—H10	120.5
H1A—C1—H1C	109.5	C11—C10—H10	120.5
H1B—C1—H1C	109.5	C12—C11—C10	120.72 (15)
C3—C2—C7	118.12 (16)	C12—C11—H11	119.6
C3—C2—C1	121.15 (15)	C10—C11—H11	119.6
C7—C2—C1	120.73 (16)	C11—C12—C13	118.68 (14)
C4—C3—C2	121.42 (15)	C11—C12—C15	119.52 (14)
C4—C3—H3	119.3	C13—C12—C15	121.80 (14)
C2—C3—H3	119.3	C12—C13—C14	120.81 (14)
C3—C4—C5	120.28 (17)	C12—C13—H13	119.6
C3—C4—H4	119.9	C14—C13—H13	119.6
C5—C4—H4	119.9	C9—C14—C13	118.74 (15)
C6—C5—C4	119.25 (17)	C9—C14—H14	120.6
C6—C5—H5	120.4	C13—C14—H14	120.6
C4—C5—H5	120.4	O1—C15—C16	120.15 (16)
C7—C6—C5	119.82 (14)	O1—C15—C12	120.37 (16)
C7—C6—C8	122.62 (13)	C16—C15—C12	119.48 (15)
C5—C6—C8	117.55 (14)	C15—C16—H16A	109.5
C6—C7—C2	121.10 (14)	C15—C16—H16B	109.5
C6—C7—H7	119.4	H16A—C16—H16B	109.5
C2—C7—H7	119.4	C15—C16—H16C	109.5
O3—C8—O2	122.16 (14)	H16A—C16—H16C	109.5
O3—C8—C6	125.13 (14)	H16B—C16—H16C	109.5
O2—C8—C6	112.70 (13)	C8—O2—C9	116.74 (11)
C14—C9—C10	122.03 (14)
C7—C2—C3—C4	−0.1 (2)	C9—C10—C11—C12	0.5 (2)
C1—C2—C3—C4	−179.69 (18)	C10—C11—C12—C13	0.3 (2)
C2—C3—C4—C5	0.0 (3)	C10—C11—C12—C15	−179.06 (14)
C3—C4—C5—C6	0.4 (3)	C11—C12—C13—C14	−0.7 (2)
C4—C5—C6—C7	−0.7 (2)	C15—C12—C13—C14	178.71 (14)
C4—C5—C6—C8	178.48 (15)	C10—C9—C14—C13	0.8 (2)
C5—C6—C7—C2	0.6 (2)	O2—C9—C14—C13	176.97 (13)
C8—C6—C7—C2	−178.52 (13)	C12—C13—C14—C9	0.1 (2)
C3—C2—C7—C6	−0.2 (2)	C11—C12—C15—O1	0.9 (2)
C1—C2—C7—C6	179.38 (16)	C13—C12—C15—O1	−178.43 (16)
C7—C6—C8—O3	−178.76 (16)	C11—C12—C15—C16	−178.87 (16)
C5—C6—C8—O3	2.1 (2)	C13—C12—C15—C16	1.8 (2)
C7—C6—C8—O2	0.3 (2)	O3—C8—O2—C9	−4.9 (2)
C5—C6—C8—O2	−178.88 (14)	C6—C8—O2—C9	176.01 (13)
C14—C9—C10—C11	−1.1 (2)	C14—C9—O2—C8	100.57 (17)
O2—C9—C10—C11	−177.29 (13)	C10—C9—O2—C8	−83.11 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2	0.93	2.42	2.7439 (17)	100
C16—H16B···O1i	0.96	2.57	3.509 (3)	167
C3—H3···O3ii	0.93	2.52	3.265 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O1i	0.96	2.57	3.509 (3)	167
C3—H3⋯O3ii	0.93	2.52	3.265 (2)	137

Symmetry codes: (i) ; (ii) .