Crystal structure of 1-(8-meth-oxy-2H-chromen-3-yl)ethanone.

In the structure of the title compound, C12H12O3, the di-hydro-pyran ring is fused with the benzene ring. The di-hydro-pyran ring is in a half-chair conformation, with the ring O and methyl-ene C atoms positioned 1.367 (3) and 1.504 (4) Å, respectively, on either side of the mean plane formed by the other four atoms. The meth-oxy group is coplanar with the benzene ring to which it is connected [Cb-Cb-Om-Cm torsion angle = -0.2 (4)°; b = benzene and m = meth-oxy], and similarly the aldehyde is coplanar with respect to the double bond of the di-hydro-pyran ring [Cdh-Cdh-Ca-Oa = -178.1 (3)°; dh = di-hydro-pyran and a = aldehyde]. In the crystal, mol-ecules are linked by weak meth-yl-meth-oxy C-H⋯O hydrogen bonds into supra-molecular chains along the a-axis direction.

Related literature

For the synthesis and biological properties of chromene derivatives, see: Choi et al. (2014 ▶); Mun et al. (2012 ▶); Yoon et al. (2012 ▶). For the chromene group in natural products, see: Starks et al. (2014 ▶); Escandón-Rivera et al. (2012 ▶). For related structures, see: Yan & Zhang (2013 ▶): Yusufzai et al. (2012 ▶).

Experimental

Crystal data

C12H12O3

M = 204.22

Orthorhombic,

a = 5.1000 (4) Å

b = 12.7455 (9) Å

c = 15.130 (1) Å

V = 983.48 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.26 × 0.20 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer

7256 measured reflections

2439 independent reflections

1943 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.148

S = 1.15

2439 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, global. DOI: 10.1107/S1600536814016808/tk5330sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016808/tk5330Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016808/tk5330Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016808/tk5330fig1.tif

The mol­ecular structure of the title compound, showing the atom labelling scheme and displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814016808/tk5330fig2.tif

Part of the crystal structure with weak inter­molecular C—H⋯O hydrogen bonds shown as dashed lines.

CCDC reference: 1015076

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

C12H12O3	F(000) = 432
Mr = 204.22	Dx = 1.379 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4995 reflections
a = 5.1000 (4) Å	θ = 2.7–28.3°
b = 12.7455 (9) Å	µ = 0.10 mm−1
c = 15.130 (1) Å	T = 173 K
V = 983.48 (12) Å3	Block, white
Z = 4	0.26 × 0.20 × 0.04 mm

Bruker SMART CCD area-detector diffractometer	1943 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 28.3°, θmin = 2.1°
φ and ω scans	h = −4→6
7256 measured reflections	k = −16→16
2439 independent reflections	l = −20→19

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.8069P] where P = (Fo2 + 2Fc2)/3
2439 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.36 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
O1	0.2139 (4)	0.13132 (13)	0.78457 (12)	0.0369 (5)
C1	0.0935 (6)	0.1378 (2)	0.69905 (18)	0.0382 (6)
H1A	−0.0596	0.0900	0.6976	0.046*
H1B	0.2202	0.1130	0.6541	0.046*
C2	0.0045 (5)	0.2465 (2)	0.67470 (17)	0.0317 (5)
C3	0.1318 (5)	0.32861 (19)	0.70942 (16)	0.0315 (5)
H3	0.0841	0.3977	0.6921	0.038*
C4	0.3416 (5)	0.31384 (19)	0.77314 (16)	0.0290 (5)
C5	0.3744 (5)	0.21278 (18)	0.80743 (16)	0.0304 (5)
C6	0.5662 (5)	0.19364 (19)	0.87130 (17)	0.0323 (6)
C7	0.7236 (6)	0.27498 (19)	0.90030 (17)	0.0327 (5)
H7	0.8543	0.2621	0.9437	0.039*
C8	0.6916 (6)	0.3759 (2)	0.86613 (17)	0.0335 (6)
H8	0.8013	0.4314	0.8860	0.040*
C9	0.5011 (5)	0.39520 (19)	0.80357 (17)	0.0320 (5)
H9	0.4783	0.4642	0.7811	0.038*
C10	−0.2116 (5)	0.2531 (2)	0.61005 (18)	0.0357 (6)
O2	−0.3175 (4)	0.17219 (16)	0.58488 (14)	0.0471 (5)
C11	−0.2923 (6)	0.3576 (2)	0.57362 (18)	0.0414 (7)
H11A	−0.1666	0.3797	0.5283	0.062*
H11B	−0.2956	0.4095	0.6214	0.062*
H11C	−0.4673	0.3519	0.5473	0.062*
O3	0.5790 (4)	0.09230 (15)	0.90143 (14)	0.0430 (5)
C12	0.7723 (6)	0.0714 (2)	0.9676 (2)	0.0435 (7)
H12A	0.9471	0.0861	0.9437	0.065*
H12B	0.7620	−0.0025	0.9853	0.065*
H12C	0.7403	0.1162	1.0191	0.065*

	U11	U22	U33	U12	U13	U23
O1	0.0406 (10)	0.0278 (9)	0.0424 (10)	−0.0065 (8)	−0.0104 (9)	0.0029 (7)
C1	0.0443 (15)	0.0297 (12)	0.0405 (13)	−0.0008 (12)	−0.0109 (13)	−0.0034 (11)
C2	0.0296 (12)	0.0307 (12)	0.0350 (12)	0.0021 (10)	0.0010 (10)	−0.0026 (10)
C3	0.0318 (13)	0.0285 (12)	0.0341 (12)	0.0045 (10)	0.0022 (11)	−0.0001 (10)
C4	0.0286 (12)	0.0268 (11)	0.0316 (12)	0.0013 (10)	0.0034 (10)	−0.0018 (9)
C5	0.0336 (13)	0.0257 (11)	0.0318 (12)	−0.0022 (10)	0.0013 (11)	−0.0016 (9)
C6	0.0347 (13)	0.0272 (12)	0.0349 (12)	0.0009 (10)	−0.0002 (11)	0.0018 (10)
C7	0.0335 (13)	0.0334 (13)	0.0311 (12)	−0.0017 (10)	−0.0015 (11)	−0.0003 (10)
C8	0.0379 (14)	0.0285 (12)	0.0342 (12)	−0.0044 (11)	0.0000 (11)	−0.0013 (10)
C9	0.0348 (13)	0.0261 (11)	0.0351 (12)	0.0023 (10)	0.0034 (11)	−0.0016 (10)
C10	0.0340 (13)	0.0400 (14)	0.0330 (12)	0.0047 (12)	0.0014 (11)	−0.0041 (11)
O2	0.0446 (12)	0.0441 (12)	0.0527 (12)	−0.0028 (10)	−0.0110 (10)	−0.0106 (9)
C11	0.0437 (16)	0.0451 (15)	0.0354 (13)	0.0064 (14)	−0.0037 (12)	0.0011 (11)
O3	0.0498 (12)	0.0285 (9)	0.0508 (11)	−0.0036 (9)	−0.0161 (10)	0.0082 (8)
C12	0.0464 (17)	0.0345 (14)	0.0497 (16)	0.0006 (13)	−0.0131 (14)	0.0096 (12)

O1—C5	1.366 (3)	C7—C8	1.396 (3)
O1—C1	1.435 (3)	C7—H7	0.9500
C1—C2	1.504 (4)	C8—C9	1.378 (4)
C1—H1A	0.9900	C8—H8	0.9500
C1—H1B	0.9900	C9—H9	0.9500
C2—C3	1.339 (4)	C10—O2	1.224 (3)
C2—C10	1.476 (4)	C10—C11	1.499 (4)
C3—C4	1.452 (4)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
C4—C9	1.396 (3)	C11—H11C	0.9800
C4—C5	1.399 (3)	O3—C12	1.430 (3)
C5—C6	1.397 (3)	C12—H12A	0.9800
C6—O3	1.371 (3)	C12—H12B	0.9800
C6—C7	1.383 (4)	C12—H12C	0.9800
C5—O1—C1	116.2 (2)	C8—C7—H7	119.8
O1—C1—C2	113.8 (2)	C9—C8—C7	120.1 (2)
O1—C1—H1A	108.8	C9—C8—H8	120.0
C2—C1—H1A	108.8	C7—C8—H8	120.0
O1—C1—H1B	108.8	C8—C9—C4	120.3 (2)
C2—C1—H1B	108.8	C8—C9—H9	119.8
H1A—C1—H1B	107.7	C4—C9—H9	119.8
C3—C2—C10	125.3 (2)	O2—C10—C2	119.2 (2)
C3—C2—C1	118.5 (2)	O2—C10—C11	120.8 (2)
C10—C2—C1	116.1 (2)	C2—C10—C11	119.9 (2)
C2—C3—C4	121.1 (2)	C10—C11—H11A	109.5
C2—C3—H3	119.5	C10—C11—H11B	109.5
C4—C3—H3	119.5	H11A—C11—H11B	109.5
C9—C4—C5	119.5 (2)	C10—C11—H11C	109.5
C9—C4—C3	123.5 (2)	H11A—C11—H11C	109.5
C5—C4—C3	117.0 (2)	H11B—C11—H11C	109.5
O1—C5—C6	117.5 (2)	C6—O3—C12	116.2 (2)
O1—C5—C4	122.3 (2)	O3—C12—H12A	109.5
C6—C5—C4	120.1 (2)	O3—C12—H12B	109.5
O3—C6—C7	125.0 (2)	H12A—C12—H12B	109.5
O3—C6—C5	115.3 (2)	O3—C12—H12C	109.5
C7—C6—C5	119.7 (2)	H12A—C12—H12C	109.5
C6—C7—C8	120.4 (2)	H12B—C12—H12C	109.5
C6—C7—H7	119.8
C5—O1—C1—C2	−39.4 (3)	O1—C5—C6—C7	−176.4 (2)
O1—C1—C2—C3	28.1 (4)	C4—C5—C6—C7	−0.1 (4)
O1—C1—C2—C10	−154.7 (2)	O3—C6—C7—C8	−179.0 (3)
C10—C2—C3—C4	179.7 (2)	C5—C6—C7—C8	0.0 (4)
C1—C2—C3—C4	−3.5 (4)	C6—C7—C8—C9	0.5 (4)
C2—C3—C4—C9	172.2 (2)	C7—C8—C9—C4	−0.9 (4)
C2—C3—C4—C5	−10.5 (4)	C5—C4—C9—C8	0.8 (4)
C1—O1—C5—C6	−156.5 (2)	C3—C4—C9—C8	178.1 (2)
C1—O1—C5—C4	27.3 (3)	C3—C2—C10—O2	−178.1 (3)
C9—C4—C5—O1	175.8 (2)	C1—C2—C10—O2	5.0 (4)
C3—C4—C5—O1	−1.7 (4)	C3—C2—C10—C11	4.2 (4)
C9—C4—C5—C6	−0.3 (4)	C1—C2—C10—C11	−172.7 (2)
C3—C4—C5—C6	−177.7 (2)	C7—C6—O3—C12	−0.2 (4)
O1—C5—C6—O3	2.8 (3)	C5—C6—O3—C12	−179.3 (2)
C4—C5—C6—O3	179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2i	0.98	2.56	3.429 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2i	0.98	2.56	3.429 (4)	148

Symmetry code: (i) .