4,7,8-Trimethyl-2H-chromen-2-one.

The mol-ecule of the title compound, C(12)H(12)O(2), is essentially planar, with a maximum deviation from the mean plane of all non-H atoms of 0.038 (1) Å for the methyl C atom in the 8-position. The crystal structure is characterized by anti-parallel π-π stacking along the c axis, with centroid-centroid distances as short as 3.866 (1) Å. In the crystal, C-H⋯O hydrogen bonds connect the mol-ecules across the stacks into ribbons in the a-axis direction.

Related literature

For general background to the pharmacological activity of coumarin derivatives, see: Xie et al. (2001 ▶); Tanitame et al. (2004 ▶); Shao et al. (1997 ▶); Rendenbach-Müller et al. (1994 ▶); Pochet et al. (1996 ▶). For a related structure, see: Gowda et al. (2010 ▶).

Experimental

Crystal data

C12H12O2

M = 188.22

Monoclinic,

a = 7.276 (3) Å

b = 18.075 (6) Å

c = 7.246 (3) Å

β = 97.055 (5)°

V = 945.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 153 K

0.44 × 0.31 × 0.26 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

8545 measured reflections

2747 independent reflections

2176 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.112

S = 1.00

2747 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009646/ld2048sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009646/ld2048Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009646/ld2048Isup3.cml

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

C12H12O2	F(000) = 400
Mr = 188.22	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.276 (3) Å	Cell parameters from 3283 reflections
b = 18.075 (6) Å	θ = 2.3–30.0°
c = 7.246 (3) Å	µ = 0.09 mm−1
β = 97.055 (5)°	T = 153 K
V = 945.8 (6) Å3	Prism, colorless
Z = 4	0.44 × 0.31 × 0.26 mm

Rigaku AFC10/Saturn724+ diffractometer	2176 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.028
Graphite monochromator	θmax = 30.1°, θmin = 3.1°
Detector resolution: 28.5714 pixels mm-1	h = −9→10
phi and ω scans	k = −24→25
8545 measured reflections	l = −10→10
2747 independent reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0269P)2 + 0.551P] where P = (Fo2 + 2Fc2)/3
2747 reflections	(Δ/σ)max = 0.001
130 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.33 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
H2	0.8364	0.0375	0.9962	0.029*
H5	0.4346	0.2356	0.8389	0.030*
H6	0.4708	0.3629	0.8497	0.030*
H10A	0.5336	0.0381	0.8616	0.035*
H10B	0.4726	0.1097	0.7392	0.035*
H10C	0.4183	0.1026	0.9459	0.035*
H11A	0.6432	0.4698	0.9153	0.037*
H11B	0.8581	0.4625	0.8914	0.037*
H11C	0.7941	0.4634	1.0949	0.037*
H12A	1.1505	0.3139	1.1756	0.036*
H12B	1.0632	0.3953	1.1693	0.036*
H12C	1.1483	0.3633	0.9921	0.036*
C1	1.01364 (18)	0.12436 (7)	1.07922 (18)	0.0243 (3)
C2	0.84235 (18)	0.08992 (7)	1.00252 (18)	0.0244 (3)
C3	0.69054 (18)	0.12937 (7)	0.93951 (18)	0.0224 (3)
C4	0.69972 (17)	0.20939 (7)	0.94548 (17)	0.0207 (2)
C5	0.55137 (18)	0.25623 (7)	0.88512 (19)	0.0248 (3)
C6	0.57298 (19)	0.33200 (7)	0.89207 (19)	0.0251 (3)
C7	0.74262 (18)	0.36425 (7)	0.96038 (18)	0.0234 (3)
C8	0.89411 (18)	0.31925 (7)	1.02295 (18)	0.0221 (3)
C9	0.86750 (17)	0.24271 (7)	1.01382 (17)	0.0206 (2)
C10	0.51347 (19)	0.09170 (8)	0.8651 (2)	0.0296 (3)
C11	0.7611 (2)	0.44726 (7)	0.9660 (2)	0.0305 (3)
C12	1.08022 (19)	0.35066 (8)	1.0964 (2)	0.0299 (3)
O1	1.02050 (12)	0.20031 (5)	1.07807 (13)	0.0240 (2)
O2	1.15405 (14)	0.09227 (6)	1.14331 (15)	0.0338 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0259 (6)	0.0213 (6)	0.0259 (6)	0.0034 (5)	0.0042 (5)	−0.0003 (5)
C2	0.0277 (7)	0.0189 (6)	0.0268 (6)	−0.0011 (5)	0.0041 (5)	−0.0012 (5)
C3	0.0246 (6)	0.0225 (6)	0.0205 (6)	−0.0035 (5)	0.0040 (5)	−0.0007 (5)
C4	0.0213 (6)	0.0211 (6)	0.0200 (6)	−0.0004 (4)	0.0038 (5)	−0.0002 (5)
C5	0.0202 (6)	0.0273 (6)	0.0262 (6)	−0.0003 (5)	0.0001 (5)	0.0003 (5)
C6	0.0238 (6)	0.0258 (6)	0.0254 (6)	0.0048 (5)	0.0014 (5)	0.0024 (5)
C7	0.0276 (6)	0.0204 (6)	0.0223 (6)	0.0014 (5)	0.0039 (5)	0.0018 (5)
C8	0.0223 (6)	0.0222 (6)	0.0220 (6)	−0.0010 (5)	0.0028 (5)	0.0000 (5)
C9	0.0196 (6)	0.0209 (6)	0.0214 (6)	0.0018 (4)	0.0025 (5)	0.0007 (5)
C10	0.0283 (7)	0.0267 (7)	0.0329 (7)	−0.0080 (5)	0.0006 (6)	−0.0005 (6)
C11	0.0366 (8)	0.0209 (6)	0.0335 (8)	0.0024 (5)	0.0016 (6)	0.0023 (5)
C12	0.0265 (7)	0.0257 (7)	0.0359 (7)	−0.0052 (5)	−0.0021 (6)	−0.0010 (6)
O1	0.0205 (4)	0.0212 (4)	0.0296 (5)	0.0020 (3)	−0.0004 (4)	0.0000 (4)
O2	0.0287 (5)	0.0271 (5)	0.0439 (6)	0.0075 (4)	−0.0030 (4)	−0.0006 (4)

C1—C2	1.4421 (19)	C8—C12	1.5042 (18)
C2—H2	0.9500	C10—H10A	0.9800
C2—C3	1.3465 (18)	C10—H10B	0.9800
C3—C4	1.4484 (18)	C10—H10C	0.9800
C3—C10	1.4979 (18)	C11—H11A	0.9800
C4—C5	1.3990 (18)	C11—H11B	0.9800
C4—C9	1.3964 (17)	C11—H11C	0.9800
C5—H5	0.9500	C12—H12A	0.9800
C5—C6	1.3788 (19)	C12—H12B	0.9800
C6—H6	0.9500	C12—H12C	0.9800
C6—C7	1.3994 (19)	O1—C1	1.3739 (16)
C7—C8	1.3998 (18)	O1—C9	1.3842 (15)
C7—C11	1.5067 (19)	O2—C1	1.2163 (16)
C8—C9	1.3973 (18)
O1—C1—C2	117.34 (11)	C9—C8—C12	120.26 (12)
O2—C1—C2	125.95 (13)	C4—C9—C8	123.63 (11)
O2—C1—O1	116.71 (12)	O1—C9—C4	120.83 (11)
C1—C2—H2	118.8	O1—C9—C8	115.54 (11)
C3—C2—H2	118.8	H10A—C10—H10B	109.5
C3—C2—C1	122.43 (12)	H10A—C10—H10C	109.5
C2—C3—C4	119.07 (12)	H10B—C10—H10C	109.5
C2—C3—C10	120.99 (12)	C3—C10—H10A	109.5
C4—C3—C10	119.94 (12)	C3—C10—H10B	109.5
C5—C4—C3	124.33 (12)	C3—C10—H10C	109.5
C9—C4—C3	118.45 (11)	H11A—C11—H11B	109.5
C9—C4—C5	117.21 (12)	H11A—C11—H11C	109.5
C4—C5—H5	119.7	H11B—C11—H11C	109.5
C6—C5—H5	119.7	C7—C11—H11A	109.5
C6—C5—C4	120.63 (12)	C7—C11—H11B	109.5
C5—C6—H6	119.4	C7—C11—H11C	109.5
C5—C6—C7	121.22 (12)	H12A—C12—H12B	109.5
C7—C6—H6	119.4	H12A—C12—H12C	109.5
C6—C7—C8	119.86 (12)	H12B—C12—H12C	109.5
C6—C7—C11	119.76 (12)	C8—C12—H12A	109.5
C8—C7—C11	120.39 (12)	C8—C12—H12B	109.5
C7—C8—C12	122.29 (12)	C8—C12—H12C	109.5
C9—C8—C7	117.45 (12)	C1—O1—C9	121.80 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.56	3.460 (2)	159
C10—H10C···O2ii	0.98	2.54	3.493 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.56	3.460 (2)	159
C10—H10C⋯O2ii	0.98	2.54	3.493 (2)	164

Symmetry codes: (i) ; (ii) .