8-Meth-oxy-2H-chromene-3-carbaldehyde.

In the title mol-ecule, C11H10O3, the fused dihydro-pyran ring is in a half-chair conformation with the O atom and the methyl-ene C atom positioned 0.1318 (13) and 0.143 (2) Å, respectively, on either side of the mean plane formed by the other four atoms. In the crystal, weak C-H⋯O hydrogen bonds link mol-ecules along [001].

Related literature

For the synthesis and biological properties of chromene derivatives, see: Mun et al. (2012 ▶); Kallikat et al. (2011 ▶); Zhang et al. (2009 ▶); Gebhardt et al. (2007 ▶); Yoon et al. (2012 ▶). For the chromene group in natural products, see: Escandón-Rivera et al. (2012 ▶); Chen et al. (2008 ▶). For related structures, see: Yusufzai et al. (2012 ▶); Betz et al. (2011 ▶); Bardajee et al. (2007 ▶).

Experimental

Crystal data

C11H10O3

M = 190.19

Orthorhombic,

a = 6.8940 (6) Å

b = 13.2079 (11) Å

c = 20.0964 (16) Å

V = 1829.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer

12690 measured reflections

2276 independent reflections

1194 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.158

S = 0.92

2276 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.28 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047319/lh5559sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047319/lh5559Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047319/lh5559Isup3.cml

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

C11H10O3	F(000) = 800
Mr = 190.19	Dx = 1.381 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3190 reflections
a = 6.8940 (6) Å	θ = 3.1–28.2°
b = 13.2079 (11) Å	µ = 0.10 mm−1
c = 20.0964 (16) Å	T = 200 K
V = 1829.9 (3) Å3	Block, pale yellow
Z = 8	0.23 × 0.21 × 0.19 mm

Bruker SMART CCD diffractometer	1194 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Graphite monochromator	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −9→9
12690 measured reflections	k = −17→16
2276 independent reflections	l = −26→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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0862P)2] where P = (Fo2 + 2Fc2)/3
2276 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.28 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	0.1026 (2)	0.40157 (12)	0.04444 (7)	0.0583 (5)
C1	0.1052 (3)	0.47227 (17)	0.08309 (9)	0.0456 (5)
H1	0.1013	0.5387	0.0651	0.055*
C2	0.1139 (2)	0.46201 (14)	0.15445 (8)	0.0351 (4)
C3	0.1208 (3)	0.35793 (14)	0.18379 (8)	0.0381 (5)
H3A	0.0257	0.3148	0.1601	0.046*
H3B	0.2512	0.3291	0.1757	0.046*
O2	0.08111 (19)	0.35301 (9)	0.25332 (6)	0.0438 (4)
C4	0.1089 (2)	0.43707 (13)	0.29215 (8)	0.0318 (4)
C5	0.1082 (2)	0.42242 (14)	0.36068 (9)	0.0340 (4)
O3	0.09121 (18)	0.32461 (10)	0.38224 (6)	0.0450 (4)
C6	0.0786 (3)	0.30827 (18)	0.45209 (9)	0.0530 (6)
H6A	0.1980	0.3320	0.4735	0.080*
H6B	0.0616	0.2358	0.4609	0.080*
H6C	−0.0324	0.3458	0.4700	0.080*
C7	0.1241 (2)	0.50626 (15)	0.40230 (9)	0.0394 (5)
H7	0.1240	0.4974	0.4492	0.047*
C8	0.1403 (3)	0.60283 (15)	0.37558 (9)	0.0449 (5)
H8	0.1496	0.6597	0.4043	0.054*
C9	0.1428 (3)	0.61667 (15)	0.30801 (9)	0.0400 (5)
H9	0.1565	0.6829	0.2902	0.048*
C10	0.1255 (2)	0.53375 (13)	0.26518 (8)	0.0325 (4)
C11	0.1184 (2)	0.54390 (14)	0.19384 (9)	0.0351 (4)
H11	0.1170	0.6095	0.1745	0.042*

	U11	U22	U33	U12	U13	U23
O1	0.0741 (11)	0.0674 (11)	0.0334 (8)	0.0080 (8)	−0.0032 (7)	−0.0087 (7)
C1	0.0500 (12)	0.0538 (14)	0.0330 (11)	0.0056 (9)	−0.0001 (9)	0.0023 (9)
C2	0.0338 (10)	0.0450 (12)	0.0266 (10)	−0.0007 (8)	0.0004 (7)	0.0008 (8)
C3	0.0505 (12)	0.0364 (11)	0.0274 (10)	−0.0032 (8)	0.0029 (8)	−0.0036 (7)
O2	0.0709 (10)	0.0331 (8)	0.0275 (7)	−0.0052 (6)	0.0046 (6)	−0.0021 (5)
C4	0.0335 (10)	0.0324 (10)	0.0294 (10)	0.0004 (7)	0.0009 (7)	−0.0034 (7)
C5	0.0367 (10)	0.0368 (11)	0.0285 (10)	0.0030 (8)	0.0018 (7)	0.0038 (7)
O3	0.0620 (9)	0.0394 (8)	0.0335 (8)	0.0043 (6)	0.0047 (6)	0.0069 (6)
C6	0.0680 (14)	0.0563 (14)	0.0347 (11)	0.0109 (11)	0.0086 (9)	0.0144 (9)
C7	0.0438 (11)	0.0480 (12)	0.0264 (9)	0.0043 (9)	−0.0004 (7)	−0.0029 (8)
C8	0.0536 (12)	0.0419 (12)	0.0392 (11)	−0.0009 (9)	0.0001 (9)	−0.0124 (9)
C9	0.0501 (12)	0.0333 (11)	0.0365 (10)	0.0001 (8)	0.0021 (8)	−0.0017 (8)
C10	0.0313 (9)	0.0359 (11)	0.0304 (10)	0.0011 (7)	0.0012 (7)	−0.0011 (7)
C11	0.0379 (10)	0.0359 (11)	0.0315 (10)	0.0001 (8)	0.0004 (7)	0.0058 (7)

O1—C1	1.215 (2)	O3—C6	1.423 (2)
C1—C2	1.442 (2)	C6—H6A	0.9800
C1—H1	0.9500	C6—H6B	0.9800
C2—C11	1.341 (3)	C6—H6C	0.9800
C2—C3	1.497 (3)	C7—C8	1.388 (3)
C3—O2	1.425 (2)	C7—H7	0.9500
C3—H3A	0.9900	C8—C9	1.370 (2)
C3—H3B	0.9900	C8—H8	0.9500
O2—C4	1.370 (2)	C9—C10	1.398 (2)
C4—C5	1.391 (2)	C9—H9	0.9500
C4—C10	1.392 (2)	C10—C11	1.441 (2)
C5—O3	1.368 (2)	C11—H11	0.9500
C5—C7	1.392 (3)
O1—C1—C2	124.4 (2)	O3—C6—H6B	109.5
O1—C1—H1	117.8	H6A—C6—H6B	109.5
C2—C1—H1	117.8	O3—C6—H6C	109.5
C11—C2—C1	120.83 (18)	H6A—C6—H6C	109.5
C11—C2—C3	120.50 (16)	H6B—C6—H6C	109.5
C1—C2—C3	118.66 (16)	C8—C7—C5	120.32 (17)
O2—C3—C2	114.96 (14)	C8—C7—H7	119.8
O2—C3—H3A	108.5	C5—C7—H7	119.8
C2—C3—H3A	108.5	C9—C8—C7	120.46 (18)
O2—C3—H3B	108.5	C9—C8—H8	119.8
C2—C3—H3B	108.5	C7—C8—H8	119.8
H3A—C3—H3B	107.5	C8—C9—C10	120.29 (18)
C4—O2—C3	119.63 (13)	C8—C9—H9	119.9
O2—C4—C5	116.79 (16)	C10—C9—H9	119.9
O2—C4—C10	122.21 (16)	C4—C10—C9	119.08 (17)
C5—C4—C10	120.89 (16)	C4—C10—C11	118.04 (16)
O3—C5—C4	116.44 (16)	C9—C10—C11	122.86 (17)
O3—C5—C7	124.61 (16)	C2—C11—C10	120.88 (17)
C4—C5—C7	118.95 (17)	C2—C11—H11	119.6
C5—O3—C6	117.45 (15)	C10—C11—H11	119.6
O3—C6—H6A	109.5
O1—C1—C2—C11	179.25 (18)	C4—C5—C7—C8	0.1 (2)
O1—C1—C2—C3	0.2 (3)	C5—C7—C8—C9	−0.7 (3)
C11—C2—C3—O2	15.8 (2)	C7—C8—C9—C10	1.2 (3)
C1—C2—C3—O2	−165.19 (15)	O2—C4—C10—C9	176.48 (15)
C2—C3—O2—C4	−23.3 (2)	C5—C4—C10—C9	0.4 (2)
C3—O2—C4—C5	−166.65 (15)	O2—C4—C10—C11	−1.8 (2)
C3—O2—C4—C10	17.1 (2)	C5—C4—C10—C11	−177.88 (14)
O2—C4—C5—O3	3.7 (2)	C8—C9—C10—C4	−1.1 (3)
C10—C4—C5—O3	179.99 (15)	C8—C9—C10—C11	177.14 (16)
O2—C4—C5—C7	−176.19 (15)	C1—C2—C11—C10	179.49 (15)
C10—C4—C5—C7	0.1 (2)	C3—C2—C11—C10	−1.5 (2)
C4—C5—O3—C6	−176.38 (15)	C4—C10—C11—C2	−6.0 (2)
C7—C5—O3—C6	3.5 (2)	C9—C10—C11—C2	175.80 (17)
O3—C5—C7—C8	−179.85 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O1i	0.98	2.49	3.340 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O1i	0.98	2.49	3.340 (3)	145

Symmetry code: (i) .