5,6-Dimethyl-4-phenyl-2H-pyran-2-one.

In the title compound, C(13)H(12)O(2), the dihedral angle between the pyran-one and phenyl rings is 57.55 (9)°. In the crystal, the mol-ecules are linked by π-π stacking inter-actions between the parallel pyran-one rings of neighboring mol-ecules with distances of 3.5778 (11) Å and 3.3871 (11) Å between the planes. C-H⋯O interactions also occur.

Related literature

For the bioactivity of 2H-pyran-2-ones, see: Puerta et al. (2005 ▶); Thaisrivongs et al. (1998 ▶); Appendino et al. (2007 ▶). For research on functionalized allenes, see: Fan et al. (2011 ▶); Zhang et al. (2011 ▶); Xu et al. (2012 ▶).

Experimental

Crystal data

C13H12O2

M = 200.23

Monoclinic,

a = 7.654 (3) Å

b = 6.967 (3) Å

c = 20.629 (8) Å

β = 97.183 (4)°

V = 1091.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.39 × 0.37 × 0.28 mm

Data collection

Bruker SMART CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.969, T max = 0.978

7794 measured reflections

2032 independent reflections

1530 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.137

S = 1.04

2032 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812011233/vm2163sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011233/vm2163Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011233/vm2163Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812011233/vm2163Isup4.cdx

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

C13H12O2	F(000) = 424
Mr = 200.23	Dx = 1.219 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2249 reflections
a = 7.654 (3) Å	θ = 2.7–25.9°
b = 6.967 (3) Å	µ = 0.08 mm−1
c = 20.629 (8) Å	T = 296 K
β = 97.183 (4)°	Block, colourless
V = 1091.4 (7) Å3	0.39 × 0.37 × 0.28 mm
Z = 4

Bruker SMART CCD area detector diffractometer	2032 independent reflections
Radiation source: fine-focus sealed tube	1530 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
phi and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
Tmin = 0.969, Tmax = 0.978	k = −8→8
7794 measured reflections	l = −24→24

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0659P)2 + 0.2202P] where P = (Fo2 + 2Fc2)/3
2032 reflections	(Δ/σ)max = 0.001
138 parameters	Δρmax = 0.18 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.2300 (2)	0.4016 (3)	0.64903 (8)	0.0547 (4)
C2	0.1478 (3)	0.5353 (3)	0.68457 (9)	0.0749 (6)
H2	0.0883	0.6385	0.6634	0.090*
C3	0.1541 (3)	0.5154 (4)	0.75160 (10)	0.0907 (8)
H3	0.0979	0.6049	0.7753	0.109*
C4	0.2425 (3)	0.3647 (4)	0.78333 (10)	0.0894 (7)
H4	0.2464	0.3523	0.8284	0.107*
C5	0.3249 (3)	0.2329 (4)	0.74867 (10)	0.0831 (7)
H5	0.3861	0.1315	0.7703	0.100*
C6	0.3180 (3)	0.2493 (3)	0.68175 (9)	0.0651 (5)
H6	0.3727	0.1575	0.6585	0.078*
C7	0.1397 (2)	0.2616 (2)	0.47092 (8)	0.0506 (4)
C8	0.1532 (2)	0.2625 (2)	0.54020 (8)	0.0508 (4)
H8	0.1145	0.1558	0.5615	0.061*
C9	0.22072 (19)	0.4138 (2)	0.57639 (7)	0.0483 (4)
C10	0.2838 (2)	0.5790 (2)	0.54428 (8)	0.0520 (4)
C11	0.2706 (2)	0.5760 (2)	0.47847 (9)	0.0553 (4)
C12	0.3667 (3)	0.7471 (3)	0.58167 (11)	0.0771 (6)
H12A	0.4441	0.8121	0.5558	0.116*
H12B	0.4326	0.7029	0.6215	0.116*
H12C	0.2764	0.8339	0.5917	0.116*
C13	0.3217 (3)	0.7292 (3)	0.43413 (11)	0.0775 (6)
H13A	0.2281	0.8212	0.4264	0.116*
H13B	0.3434	0.6731	0.3934	0.116*
H13C	0.4265	0.7920	0.4540	0.116*
O1	0.20108 (14)	0.42248 (16)	0.44270 (5)	0.0546 (3)
O2	0.08210 (18)	0.13534 (19)	0.43387 (6)	0.0699 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0496 (9)	0.0703 (11)	0.0427 (9)	0.0008 (8)	0.0004 (7)	−0.0027 (8)
C2	0.0710 (12)	0.0994 (15)	0.0514 (10)	0.0218 (11)	−0.0034 (9)	−0.0120 (10)
C3	0.0787 (14)	0.141 (2)	0.0513 (11)	0.0202 (14)	0.0051 (10)	−0.0242 (13)
C4	0.0815 (14)	0.143 (2)	0.0420 (10)	−0.0013 (15)	0.0022 (10)	0.0023 (13)
C5	0.0916 (15)	0.1017 (17)	0.0535 (12)	0.0055 (13)	−0.0009 (11)	0.0162 (11)
C6	0.0736 (12)	0.0735 (12)	0.0476 (10)	0.0039 (9)	0.0052 (8)	0.0042 (9)
C7	0.0523 (9)	0.0550 (10)	0.0451 (9)	0.0090 (7)	0.0079 (7)	0.0006 (8)
C8	0.0529 (9)	0.0560 (10)	0.0439 (9)	0.0036 (7)	0.0078 (7)	0.0037 (7)
C9	0.0434 (8)	0.0565 (9)	0.0443 (9)	0.0069 (7)	0.0020 (6)	0.0004 (7)
C10	0.0449 (9)	0.0502 (9)	0.0600 (10)	0.0062 (7)	0.0025 (7)	0.0014 (8)
C11	0.0469 (9)	0.0566 (10)	0.0640 (11)	0.0104 (8)	0.0129 (8)	0.0110 (8)
C12	0.0726 (13)	0.0640 (12)	0.0910 (15)	−0.0060 (10)	−0.0045 (11)	−0.0075 (10)
C13	0.0767 (13)	0.0691 (12)	0.0903 (15)	0.0091 (10)	0.0243 (11)	0.0282 (11)
O1	0.0615 (7)	0.0583 (7)	0.0452 (6)	0.0088 (6)	0.0109 (5)	0.0054 (5)
O2	0.0899 (10)	0.0664 (8)	0.0532 (7)	−0.0013 (7)	0.0083 (7)	−0.0133 (6)

C1—C2	1.384 (3)	C7—C8	1.420 (2)
C1—C6	1.387 (2)	C8—C9	1.356 (2)
C1—C9	1.494 (2)	C8—H8	0.9300
C2—C3	1.384 (3)	C9—C10	1.440 (2)
C2—H2	0.9300	C10—C11	1.349 (2)
C3—C4	1.370 (3)	C10—C12	1.499 (2)
C3—H3	0.9300	C11—O1	1.369 (2)
C4—C5	1.366 (3)	C11—C13	1.489 (2)
C4—H4	0.9300	C12—H12A	0.9600
C5—C6	1.380 (3)	C12—H12B	0.9600
C5—H5	0.9300	C12—H12C	0.9600
C6—H6	0.9300	C13—H13A	0.9600
C7—O2	1.212 (2)	C13—H13B	0.9600
C7—O1	1.373 (2)	C13—H13C	0.9600
C2—C1—C6	118.86 (16)	C7—C8—H8	118.9
C2—C1—C9	121.69 (16)	C8—C9—C10	119.63 (15)
C6—C1—C9	119.41 (15)	C8—C9—C1	118.35 (15)
C1—C2—C3	120.0 (2)	C10—C9—C1	122.01 (15)
C1—C2—H2	120.0	C11—C10—C9	117.62 (15)
C3—C2—H2	120.0	C11—C10—C12	120.21 (17)
C4—C3—C2	120.5 (2)	C9—C10—C12	122.14 (16)
C4—C3—H3	119.7	C10—C11—O1	121.97 (15)
C2—C3—H3	119.7	C10—C11—C13	127.95 (18)
C5—C4—C3	119.86 (19)	O1—C11—C13	110.07 (16)
C5—C4—H4	120.1	C10—C12—H12A	109.5
C3—C4—H4	120.1	C10—C12—H12B	109.5
C4—C5—C6	120.4 (2)	H12A—C12—H12B	109.5
C4—C5—H5	119.8	C10—C12—H12C	109.5
C6—C5—H5	119.8	H12A—C12—H12C	109.5
C5—C6—C1	120.39 (19)	H12B—C12—H12C	109.5
C5—C6—H6	119.8	C11—C13—H13A	109.5
C1—C6—H6	119.8	C11—C13—H13B	109.5
O2—C7—O1	116.24 (15)	H13A—C13—H13B	109.5
O2—C7—C8	127.79 (16)	C11—C13—H13C	109.5
O1—C7—C8	115.97 (14)	H13A—C13—H13C	109.5
C9—C8—C7	122.13 (15)	H13B—C13—H13C	109.5
C9—C8—H8	118.9	C11—O1—C7	122.68 (13)
C6—C1—C2—C3	−0.1 (3)	C2—C1—C9—C10	59.0 (2)
C9—C1—C2—C3	177.71 (19)	C6—C1—C9—C10	−123.23 (18)
C1—C2—C3—C4	0.5 (4)	C8—C9—C10—C11	0.7 (2)
C2—C3—C4—C5	−0.1 (4)	C1—C9—C10—C11	179.62 (14)
C3—C4—C5—C6	−0.7 (4)	C8—C9—C10—C12	−177.38 (15)
C4—C5—C6—C1	1.2 (3)	C1—C9—C10—C12	1.5 (2)
C2—C1—C6—C5	−0.8 (3)	C9—C10—C11—O1	−0.3 (2)
C9—C1—C6—C5	−178.59 (17)	C12—C10—C11—O1	177.82 (15)
O2—C7—C8—C9	179.99 (16)	C9—C10—C11—C13	178.38 (16)
O1—C7—C8—C9	0.7 (2)	C12—C10—C11—C13	−3.5 (3)
C7—C8—C9—C10	−1.0 (2)	C10—C11—O1—C7	0.1 (2)
C7—C8—C9—C1	−179.88 (14)	C13—C11—O1—C7	−178.77 (14)
C2—C1—C9—C8	−122.10 (19)	O2—C7—O1—C11	−179.66 (14)
C6—C1—C9—C8	55.7 (2)	C8—C7—O1—C11	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.93	2.53	3.384 (2)	152
C13—H13A···O2ii	0.96	2.47	3.372 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.93	2.53	3.384 (2)	152
C13—H13A⋯O2ii	0.96	2.47	3.372 (3)	156

Symmetry codes: (i) ; (ii) .