2-(4-Fluoro-phen-yl)-2H-chromen-4(3H)-one.

In the crystal structure of the title compound, C(15)H(11)FO(2), mol-ecules form inversion dimers through pairs of weak C-H⋯O hydrogen bonds. Dimers oriented in parallel, linked by C-H⋯π contacts, are arranged in columns along the b axis. The fluoro-phenyl ring and the benzene ring of the 2H-chromen-4(3H)-one unit are inclined to one another by 70.41 (16)°. They are respectively parallel in a given column or almost perpendicular [oriented at an angle of 87.8 (1)°] in neighbouring (inversely oriented) columns, forming a herringbone pattern.

Related literature

For general background to flavanones, see: Grayer & Veitch (2006 ▶); Nijveldt et al. (2001 ▶). For related structures, see: Białońska et al. (2007a ▶,b ▶). For inter­molecular inter­actions, see: Novoa et al. (2006 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Aitmambetov & Kubzheterova (2002 ▶); Chen et al. (2011 ▶); Wera et al. (2010 ▶).

Experimental

Crystal data

C15H11FO2

M = 242.24

Monoclinic,

a = 11.7896 (13) Å

b = 5.2309 (8) Å

c = 19.740 (3) Å

β = 91.630 (11)°

V = 1216.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.6 × 0.05 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.919, T max = 0.953

7630 measured reflections

2163 independent reflections

1080 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.160

S = 1.01

2163 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681105464X/xu5408sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105464X/xu5408Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681105464X/xu5408Isup3.cml

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

C15H11FO2	F(000) = 504
Mr = 242.24	Dx = 1.322 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2163 reflections
a = 11.7896 (13) Å	θ = 3.5–25.1°
b = 5.2309 (8) Å	µ = 0.10 mm−1
c = 19.740 (3) Å	T = 295 K
β = 91.630 (11)°	Needle, colorless
V = 1216.9 (3) Å3	0.6 × 0.05 × 0.05 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	2163 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1080 reflections with I > 2σ(I)
graphite	Rint = 0.080
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.5°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −5→6
Tmin = 0.919, Tmax = 0.953	l = −18→23
7630 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.160	w = 1/[σ2(Fo2) + (0.0555P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2163 reflections	Δρmax = 0.18 e Å−3
164 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (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	0.81543 (15)	0.0853 (4)	0.03640 (10)	0.0584 (6)
C2	0.7340 (2)	0.1581 (6)	−0.01647 (15)	0.0559 (8)
H2	0.7041	0.0020	−0.0379	0.067*
C3	0.6364 (2)	0.3003 (6)	0.01423 (16)	0.0604 (9)
H3A	0.6643	0.4583	0.0343	0.072*
H3B	0.5811	0.3439	−0.0212	0.072*
C4	0.5800 (3)	0.1446 (6)	0.06728 (16)	0.0580 (8)
C5	0.6150 (3)	−0.1982 (6)	0.15344 (17)	0.0691 (10)
H5	0.5387	−0.1907	0.1641	0.083*
C6	0.6851 (4)	−0.3619 (7)	0.18806 (18)	0.0788 (11)
H6	0.6563	−0.4688	0.2210	0.095*
C7	0.7999 (3)	−0.3687 (7)	0.17398 (18)	0.0777 (11)
H7	0.8482	−0.4776	0.1983	0.093*
C8	0.8424 (3)	−0.2147 (6)	0.12410 (16)	0.0638 (9)
H8	0.9194	−0.2177	0.1150	0.077*
C9	0.6553 (3)	−0.0420 (5)	0.10249 (15)	0.0541 (8)
C10	0.7694 (3)	−0.0553 (5)	0.08754 (15)	0.0533 (8)
O11	0.48046 (18)	0.1698 (4)	0.08060 (13)	0.0784 (8)
C12	0.7935 (2)	0.3105 (6)	−0.06892 (16)	0.0545 (8)
C13	0.7726 (3)	0.2659 (7)	−0.13661 (19)	0.0813 (11)
H13	0.7243	0.1333	−0.1498	0.098*
C14	0.8221 (4)	0.4146 (8)	−0.1857 (2)	0.0939 (12)
H14	0.8077	0.3834	−0.2315	0.113*
C15	0.8924 (3)	0.6075 (8)	−0.1651 (2)	0.0766 (11)
C16	0.9173 (3)	0.6583 (6)	−0.0993 (2)	0.0720 (10)
H16	0.9666	0.7901	−0.0869	0.086*
C17	0.8669 (2)	0.5075 (6)	−0.05082 (17)	0.0635 (9)
H17	0.8826	0.5394	−0.0052	0.076*
F18	0.94093 (19)	0.7554 (5)	−0.21355 (12)	0.1139 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0545 (11)	0.0636 (13)	0.0569 (14)	0.0006 (10)	0.0003 (10)	0.0084 (11)
C2	0.0576 (18)	0.0598 (18)	0.050 (2)	0.0043 (15)	−0.0027 (15)	0.0036 (15)
C3	0.0594 (19)	0.0567 (18)	0.065 (2)	0.0072 (15)	0.0073 (16)	−0.0005 (16)
C4	0.0558 (19)	0.0593 (19)	0.059 (2)	−0.0006 (16)	0.0078 (16)	−0.0073 (16)
C5	0.079 (2)	0.069 (2)	0.060 (2)	0.0009 (19)	0.0113 (18)	−0.0054 (19)
C6	0.110 (3)	0.073 (2)	0.054 (2)	−0.004 (2)	0.016 (2)	0.0065 (18)
C7	0.101 (3)	0.072 (2)	0.060 (3)	0.011 (2)	−0.001 (2)	0.0089 (19)
C8	0.074 (2)	0.062 (2)	0.055 (2)	0.0056 (17)	−0.0002 (17)	0.0027 (17)
C9	0.065 (2)	0.0502 (17)	0.047 (2)	−0.0017 (15)	0.0066 (15)	−0.0043 (15)
C10	0.064 (2)	0.0491 (17)	0.0470 (19)	−0.0003 (15)	0.0034 (15)	−0.0043 (15)
O11	0.0585 (14)	0.0875 (17)	0.0899 (19)	0.0026 (12)	0.0133 (12)	0.0015 (14)
C12	0.0569 (18)	0.0570 (18)	0.050 (2)	0.0061 (15)	0.0045 (15)	−0.0055 (16)
C13	0.102 (3)	0.082 (3)	0.059 (3)	−0.010 (2)	−0.006 (2)	−0.001 (2)
C14	0.124 (3)	0.107 (3)	0.051 (3)	−0.010 (3)	0.001 (2)	0.011 (2)
C15	0.078 (2)	0.088 (3)	0.065 (3)	0.009 (2)	0.018 (2)	0.027 (2)
C16	0.068 (2)	0.073 (2)	0.077 (3)	−0.0060 (18)	0.018 (2)	0.005 (2)
C17	0.064 (2)	0.072 (2)	0.055 (2)	−0.0004 (18)	0.0090 (16)	−0.0048 (18)
F18	0.1241 (18)	0.1279 (19)	0.0916 (18)	0.0035 (15)	0.0346 (14)	0.0416 (15)

O1—C10	1.373 (3)	C7—H7	0.9300
O1—C2	1.449 (3)	C8—C10	1.386 (4)
C2—C12	1.497 (4)	C8—H8	0.9300
C2—C3	1.512 (4)	C9—C10	1.388 (4)
C2—H2	0.9800	C12—C13	1.372 (4)
C3—C4	1.497 (4)	C12—C17	1.386 (4)
C3—H3A	0.9700	C13—C14	1.384 (5)
C3—H3B	0.9700	C13—H13	0.9300
C4—O11	1.217 (3)	C14—C15	1.361 (5)
C4—C9	1.479 (4)	C14—H14	0.9300
C5—C6	1.360 (5)	C15—C16	1.350 (5)
C5—C9	1.390 (4)	C15—F18	1.367 (4)
C5—H5	0.9300	C16—C17	1.387 (4)
C6—C7	1.389 (5)	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.378 (4)
C10—O1—C2	113.7 (2)	C7—C8—H8	120.3
O1—C2—C12	108.9 (2)	C10—C8—H8	120.3
O1—C2—C3	109.7 (2)	C10—C9—C5	118.5 (3)
C12—C2—C3	113.1 (2)	C10—C9—C4	120.4 (3)
O1—C2—H2	108.3	C5—C9—C4	121.0 (3)
C12—C2—H2	108.3	O1—C10—C8	116.9 (3)
C3—C2—H2	108.3	O1—C10—C9	122.4 (3)
C4—C3—C2	111.8 (2)	C8—C10—C9	120.7 (3)
C4—C3—H3A	109.3	C13—C12—C17	118.1 (3)
C2—C3—H3A	109.3	C13—C12—C2	120.6 (3)
C4—C3—H3B	109.3	C17—C12—C2	121.3 (3)
C2—C3—H3B	109.3	C12—C13—C14	121.2 (4)
H3A—C3—H3B	107.9	C12—C13—H13	119.4
O11—C4—C9	122.6 (3)	C14—C13—H13	119.4
O11—C4—C3	122.8 (3)	C15—C14—C13	118.2 (4)
C9—C4—C3	114.5 (3)	C15—C14—H14	120.9
C6—C5—C9	121.2 (3)	C13—C14—H14	120.9
C6—C5—H5	119.4	C16—C15—C14	123.2 (3)
C9—C5—H5	119.4	C16—C15—F18	118.5 (4)
C5—C6—C7	119.8 (3)	C14—C15—F18	118.3 (4)
C5—C6—H6	120.1	C15—C16—C17	117.8 (3)
C7—C6—H6	120.1	C15—C16—H16	121.1
C8—C7—C6	120.3 (3)	C17—C16—H16	121.1
C8—C7—H7	119.8	C12—C17—C16	121.4 (3)
C6—C7—H7	119.8	C12—C17—H17	119.3
C7—C8—C10	119.4 (3)	C16—C17—H17	119.3
C10—O1—C2—C12	179.8 (2)	C5—C9—C10—O1	177.6 (3)
C10—O1—C2—C3	55.5 (3)	C4—C9—C10—O1	−5.6 (4)
O1—C2—C3—C4	−57.2 (3)	C5—C9—C10—C8	−2.1 (4)
C12—C2—C3—C4	−179.0 (3)	C4—C9—C10—C8	174.7 (3)
C2—C3—C4—O11	−152.0 (3)	O1—C2—C12—C13	136.3 (3)
C2—C3—C4—C9	28.3 (4)	C3—C2—C12—C13	−101.4 (3)
C9—C5—C6—C7	2.0 (5)	O1—C2—C12—C17	−46.7 (3)
C5—C6—C7—C8	−1.5 (5)	C3—C2—C12—C17	75.5 (4)
C6—C7—C8—C10	−0.8 (5)	C17—C12—C13—C14	−0.7 (5)
C6—C5—C9—C10	−0.2 (5)	C2—C12—C13—C14	176.4 (3)
C6—C5—C9—C4	−177.0 (3)	C12—C13—C14—C15	−0.1 (6)
O11—C4—C9—C10	−177.1 (3)	C13—C14—C15—C16	0.9 (6)
C3—C4—C9—C10	2.6 (4)	C13—C14—C15—F18	−179.7 (3)
O11—C4—C9—C5	−0.3 (5)	C14—C15—C16—C17	−1.0 (5)
C3—C4—C9—C5	179.4 (3)	F18—C15—C16—C17	179.6 (3)
C2—O1—C10—C8	155.0 (3)	C13—C12—C17—C16	0.6 (5)
C2—O1—C10—C9	−24.7 (4)	C2—C12—C17—C16	−176.4 (3)
C7—C8—C10—O1	−177.1 (3)	C15—C16—C17—C12	0.2 (5)
C7—C8—C10—C9	2.6 (5)

Cg1 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O11i	0.98	2.48	3.280 (4)	139
C3—H3A···Cg1ii	0.97	2.78	3.695 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O11i	0.98	2.48	3.280 (4)	139
C3—H3A⋯Cg1ii	0.97	2.78	3.695 (3)	157

Symmetry codes: (i) ; (ii) .