7-Fluoro-4-oxochromene-3-carbaldehyde.

In the title compound, C(10)H(5)FO(3), the chromenone ring is essentially planar, with a maximum deviation of 0.039 (1) Å. The dihedral angle between the fluoro-subsituted benzene ring and the pyran ring is 1.92 (4)°. In the crystal, mol-ecules are connected via weak inter-molecular C-H⋯O hydrogen bonds, forming supra-molecular ribbons along the b axis. These ribbons are stacked down the a axis.

Related literature

For the biological activity of chromones, see: Masami et al. (2007 ▶); Ellis et al. (1978 ▶); Raj et al. (2010 ▶); Nawrot-Modranka et al. (2006 ▶); Gomes et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H5FO3

M = 192.14

Monoclinic,

a = 3.7294 (1) Å

b = 6.2347 (2) Å

c = 34.6518 (11) Å

β = 90.740 (1)°

V = 805.65 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.52 × 0.20 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.935, T max = 0.990

20369 measured reflections

2937 independent reflections

2622 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.03

2937 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.18 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007045/rz2562sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007045/rz2562Isup2.hkl

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

C10H5FO3	F(000) = 392
Mr = 192.14	Dx = 1.584 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9357 reflections
a = 3.7294 (1) Å	θ = 3.3–32.6°
b = 6.2347 (2) Å	µ = 0.13 mm−1
c = 34.6518 (11) Å	T = 100 K
β = 90.740 (1)°	Plate, yellow
V = 805.65 (4) Å3	0.52 × 0.20 × 0.08 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	2937 independent reflections
Radiation source: fine-focus sealed tube	2622 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 32.6°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.935, Tmax = 0.990	k = −9→9
20369 measured reflections	l = −51→52

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0705P)2 + 0.3007P] where P = (Fo2 + 2Fc2)/3
2937 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
F1	0.11979 (18)	0.11518 (12)	0.279011 (18)	0.02856 (16)
O1	0.12537 (18)	0.31079 (11)	0.409211 (19)	0.01826 (15)
O2	0.6366 (2)	0.87750 (12)	0.38719 (2)	0.02381 (17)
O3	0.2976 (2)	0.75507 (14)	0.49717 (2)	0.02861 (18)
C1	0.1927 (2)	0.45457 (15)	0.43718 (2)	0.01768 (17)
H1A	0.1255	0.4194	0.4621	0.021*
C2	0.2137 (2)	0.36246 (14)	0.37194 (2)	0.01554 (16)
C3	0.1252 (2)	0.20906 (15)	0.34431 (3)	0.01823 (17)
H3A	0.0180	0.0796	0.3508	0.022*
C4	0.2053 (2)	0.25964 (16)	0.30674 (3)	0.01986 (18)
C5	0.3659 (2)	0.45082 (17)	0.29548 (3)	0.02122 (19)
H5A	0.4134	0.4783	0.2697	0.025*
C6	0.4525 (2)	0.59831 (16)	0.32376 (3)	0.01913 (18)
H6A	0.5617	0.7268	0.3170	0.023*
C7	0.3775 (2)	0.55659 (14)	0.36268 (2)	0.01570 (16)
C8	0.4695 (2)	0.71039 (14)	0.39326 (3)	0.01698 (17)
C9	0.3518 (2)	0.64737 (15)	0.43164 (3)	0.01704 (17)
C10	0.4046 (3)	0.79260 (17)	0.46468 (3)	0.02236 (19)
H10A	0.5266	0.9205	0.4606	0.027*

	U11	U22	U33	U12	U13	U23
F1	0.0312 (3)	0.0358 (4)	0.0187 (3)	−0.0032 (3)	0.0015 (2)	−0.0083 (2)
O1	0.0214 (3)	0.0184 (3)	0.0151 (3)	−0.0049 (2)	0.0026 (2)	0.0025 (2)
O2	0.0249 (3)	0.0205 (3)	0.0260 (3)	−0.0073 (3)	0.0031 (3)	0.0042 (3)
O3	0.0367 (4)	0.0295 (4)	0.0198 (3)	−0.0090 (3)	0.0056 (3)	−0.0039 (3)
C1	0.0181 (4)	0.0201 (4)	0.0149 (3)	−0.0024 (3)	0.0014 (3)	0.0023 (3)
C2	0.0140 (3)	0.0185 (4)	0.0141 (3)	−0.0006 (3)	0.0022 (3)	0.0030 (3)
C3	0.0164 (4)	0.0203 (4)	0.0180 (4)	−0.0014 (3)	0.0014 (3)	0.0008 (3)
C4	0.0169 (4)	0.0264 (4)	0.0162 (4)	0.0007 (3)	0.0000 (3)	−0.0022 (3)
C5	0.0182 (4)	0.0300 (5)	0.0155 (4)	0.0007 (3)	0.0024 (3)	0.0044 (3)
C6	0.0162 (4)	0.0233 (4)	0.0179 (4)	−0.0007 (3)	0.0025 (3)	0.0064 (3)
C7	0.0133 (3)	0.0178 (4)	0.0160 (3)	−0.0004 (3)	0.0012 (3)	0.0037 (3)
C8	0.0145 (3)	0.0178 (4)	0.0187 (4)	−0.0007 (3)	0.0016 (3)	0.0043 (3)
C9	0.0164 (3)	0.0185 (4)	0.0162 (3)	−0.0023 (3)	0.0006 (3)	0.0013 (3)
C10	0.0244 (4)	0.0230 (4)	0.0198 (4)	−0.0041 (3)	0.0010 (3)	−0.0013 (3)

F1—C4	1.3521 (11)	C3—H3A	0.9300
O1—C1	1.3414 (11)	C4—C5	1.3921 (14)
O1—C2	1.3751 (10)	C5—C6	1.3791 (14)
O2—C8	1.2334 (11)	C5—H5A	0.9300
O3—C10	1.2218 (12)	C6—C7	1.4052 (12)
C1—C9	1.3551 (12)	C6—H6A	0.9300
C1—H1A	0.9300	C7—C8	1.4664 (13)
C2—C3	1.3902 (12)	C8—C9	1.4599 (12)
C2—C7	1.3950 (12)	C9—C10	1.4711 (13)
C3—C4	1.3759 (12)	C10—H10A	0.9300
C1—O1—C2	118.49 (7)	C5—C6—C7	120.72 (9)
O1—C1—C9	124.66 (8)	C5—C6—H6A	119.6
O1—C1—H1A	117.7	C7—C6—H6A	119.6
C9—C1—H1A	117.7	C2—C7—C6	118.33 (8)
O1—C2—C3	115.35 (8)	C2—C7—C8	120.02 (8)
O1—C2—C7	122.02 (8)	C6—C7—C8	121.65 (8)
C3—C2—C7	122.63 (8)	O2—C8—C9	122.77 (9)
C4—C3—C2	116.20 (9)	O2—C8—C7	122.90 (8)
C4—C3—H3A	121.9	C9—C8—C7	114.32 (8)
C2—C3—H3A	121.9	C1—C9—C8	120.34 (8)
F1—C4—C3	117.88 (9)	C1—C9—C10	119.36 (8)
F1—C4—C5	118.01 (8)	C8—C9—C10	120.30 (8)
C3—C4—C5	124.11 (9)	O3—C10—C9	123.87 (9)
C6—C5—C4	118.01 (8)	O3—C10—H10A	118.1
C6—C5—H5A	121.0	C9—C10—H10A	118.1
C4—C5—H5A	121.0
C2—O1—C1—C9	−1.81 (13)	C5—C6—C7—C2	0.03 (13)
C1—O1—C2—C3	−177.90 (8)	C5—C6—C7—C8	179.56 (8)
C1—O1—C2—C7	1.50 (12)	C2—C7—C8—O2	174.82 (8)
O1—C2—C3—C4	178.80 (8)	C6—C7—C8—O2	−4.70 (14)
C7—C2—C3—C4	−0.59 (13)	C2—C7—C8—C9	−4.23 (12)
C2—C3—C4—F1	−179.36 (8)	C6—C7—C8—C9	176.24 (8)
C2—C3—C4—C5	0.09 (14)	O1—C1—C9—C8	−1.12 (14)
F1—C4—C5—C6	179.89 (8)	O1—C1—C9—C10	178.88 (9)
C3—C4—C5—C6	0.45 (15)	O2—C8—C9—C1	−175.04 (9)
C4—C5—C6—C7	−0.49 (14)	C7—C8—C9—C1	4.01 (12)
O1—C2—C7—C6	−178.81 (8)	O2—C8—C9—C10	4.95 (14)
C3—C2—C7—C6	0.54 (13)	C7—C8—C9—C10	−175.99 (8)
O1—C2—C7—C8	1.65 (13)	C1—C9—C10—O3	−3.67 (15)
C3—C2—C7—C8	−178.99 (8)	C8—C9—C10—O3	176.33 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3i	0.93	2.39	3.2147 (11)	148
C3—H3A···O2ii	0.93	2.29	3.1419 (12)	152
C10—H10A···O3iii	0.93	2.58	3.3010 (14)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3i	0.93	2.39	3.2147 (11)	148
C3—H3A⋯O2ii	0.93	2.29	3.1419 (12)	152
C10—H10A⋯O3iii	0.93	2.58	3.3010 (14)	135

Symmetry codes: (i) ; (ii) ; (iii) .