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

In the crystal structure of the title compound, C(15)H(9)FO(3), inversely oriented mol-ecules form inversion dimers through pairs of O-H⋯O hydrogen bonds. The benzene ring is twisted at an angle of 12.0 (1)° relative to the 4H-chromene skeleton of the mol-ecule. Adjacent 4H-chromene units are parallel in a given column or oriented at an angle of 50.0 (1)° in neighboring, inversely oriented, columns, forming a herringbone pattern.

Related literature

For general background to fluorescence in flavanol (3-hy­droxy-2-phenyl-4H-chromen-4-one) and its derivatives, see: Demchenko et al. (2002 ▶); Pivovarenko et al. (2005 ▶); Roshal et al. (2003 ▶); Sengupta & Kasha (1979 ▶). For related structures, see: Cantrell & Stalzer (1982 ▶); Etter et al. (1986 ▶); Waller et al. (2003 ▶). For inter­molecular inter­actions, see: Aakeröy et al. (1992 ▶); Dorn et al. (2005 ▶). For the synthesis, see: Smith et al. (1968 ▶).

Experimental

Crystal data

C15H9FO3

M = 256.22

Monoclinic,

a = 15.5971 (9) Å

b = 3.8790 (2) Å

c = 19.1655 (12) Å

β = 103.906 (6)°

V = 1125.55 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.6 × 0.4 × 0.05 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.956, T max = 0.991

7973 measured reflections

1999 independent reflections

1729 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.113

S = 1.12

1999 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.21 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 datablocks global, I. DOI: 10.1107/S1600536810045083/xu5076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045083/xu5076Isup2.hkl

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

C15H9FO3	F(000) = 528
Mr = 256.22	Dx = 1.512 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1729 reflections
a = 15.5971 (9) Å	θ = 3.9–25.1°
b = 3.8790 (2) Å	µ = 0.12 mm−1
c = 19.1655 (12) Å	T = 295 K
β = 103.906 (6)°	Plate, yellow
V = 1125.55 (11) Å3	0.6 × 0.4 × 0.05 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	1999 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1729 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.9°
ω scans	h = −18→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −4→4
Tmin = 0.956, Tmax = 0.991	l = −20→22
7973 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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0392P)2 + 0.833P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
1999 reflections	Δρmax = 0.21 e Å−3
176 parameters	Δρmin = −0.21 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: 0.010 (2)

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	0.78326 (8)	0.9690 (4)	0.42669 (7)	0.0375 (4)
C2	0.75381 (12)	0.8861 (5)	0.48666 (10)	0.0305 (5)
C3	0.66843 (13)	0.9437 (6)	0.48778 (10)	0.0340 (5)
C4	0.60607 (13)	1.0994 (6)	0.42768 (11)	0.0350 (5)
C5	0.58939 (13)	1.3469 (6)	0.30419 (11)	0.0376 (5)
H5	0.5310	1.4047	0.3022	0.045*
C6	0.62406 (14)	1.4144 (6)	0.24658 (12)	0.0421 (6)
H6	0.5891	1.5134	0.2052	0.051*
C7	0.71196 (15)	1.3346 (7)	0.25000 (12)	0.0442 (6)
H7	0.7354	1.3816	0.2108	0.053*
C8	0.76441 (14)	1.1878 (7)	0.31031 (11)	0.0423 (6)
H8	0.8232	1.1364	0.3124	0.051*
C9	0.64095 (12)	1.1912 (5)	0.36633 (10)	0.0306 (5)
C10	0.72829 (12)	1.1169 (6)	0.36824 (10)	0.0320 (5)
O11	0.63946 (10)	0.8624 (5)	0.54678 (8)	0.0542 (5)
H11	0.585 (2)	0.891 (9)	0.5380 (16)	0.081*
O12	0.52826 (9)	1.1478 (5)	0.42954 (9)	0.0554 (5)
C13	0.82586 (12)	0.7435 (5)	0.54311 (10)	0.0306 (5)
C14	0.91251 (13)	0.7678 (6)	0.53545 (11)	0.0389 (5)
H14	0.9230	0.8692	0.4943	0.047*
C15	0.98280 (14)	0.6447 (6)	0.58754 (11)	0.0420 (6)
H15	1.0402	0.6623	0.5818	0.050*
C16	0.96660 (13)	0.4969 (6)	0.64746 (11)	0.0369 (5)
C17	0.88298 (14)	0.4651 (6)	0.65736 (11)	0.0406 (6)
H17	0.8736	0.3620	0.6987	0.049*
C18	0.81276 (13)	0.5880 (6)	0.60519 (11)	0.0366 (5)
H18	0.7557	0.5667	0.6116	0.044*
F19	1.03595 (8)	0.3745 (4)	0.69849 (7)	0.0561 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0255 (7)	0.0598 (10)	0.0287 (7)	0.0049 (7)	0.0097 (6)	0.0056 (7)
C2	0.0284 (10)	0.0368 (12)	0.0278 (10)	−0.0038 (9)	0.0098 (8)	−0.0027 (9)
C3	0.0294 (10)	0.0435 (12)	0.0310 (10)	−0.0026 (10)	0.0109 (8)	−0.0009 (10)
C4	0.0262 (10)	0.0423 (12)	0.0375 (11)	−0.0016 (9)	0.0095 (9)	−0.0022 (10)
C5	0.0281 (10)	0.0424 (13)	0.0409 (12)	0.0012 (9)	0.0053 (9)	0.0008 (10)
C6	0.0402 (12)	0.0492 (14)	0.0346 (11)	0.0048 (11)	0.0043 (9)	0.0049 (11)
C7	0.0427 (12)	0.0580 (15)	0.0343 (11)	0.0027 (11)	0.0140 (10)	0.0054 (11)
C8	0.0314 (11)	0.0615 (16)	0.0363 (11)	0.0035 (11)	0.0129 (9)	0.0020 (11)
C9	0.0265 (10)	0.0340 (11)	0.0314 (10)	−0.0030 (9)	0.0068 (8)	−0.0043 (9)
C10	0.0263 (10)	0.0402 (12)	0.0284 (10)	−0.0014 (9)	0.0045 (8)	−0.0028 (9)
O11	0.0303 (8)	0.0941 (15)	0.0432 (9)	0.0096 (9)	0.0185 (7)	0.0201 (9)
O12	0.0274 (8)	0.0902 (14)	0.0523 (10)	0.0100 (9)	0.0169 (7)	0.0174 (10)
C13	0.0280 (10)	0.0351 (11)	0.0292 (10)	−0.0022 (9)	0.0081 (8)	−0.0043 (9)
C14	0.0331 (11)	0.0515 (14)	0.0342 (11)	−0.0001 (10)	0.0122 (9)	0.0077 (10)
C15	0.0267 (10)	0.0566 (15)	0.0429 (12)	−0.0002 (10)	0.0090 (9)	0.0054 (11)
C16	0.0327 (11)	0.0424 (13)	0.0320 (11)	0.0020 (10)	0.0010 (9)	0.0002 (10)
C17	0.0392 (12)	0.0537 (15)	0.0302 (11)	−0.0035 (11)	0.0109 (9)	0.0040 (10)
C18	0.0287 (10)	0.0497 (13)	0.0328 (11)	−0.0027 (10)	0.0100 (8)	0.0006 (10)
F19	0.0386 (7)	0.0798 (11)	0.0443 (8)	0.0069 (7)	−0.0013 (6)	0.0139 (7)

O1—C10	1.363 (2)	C8—C10	1.388 (3)
O1—C2	1.374 (2)	C8—H8	0.9300
C2—C3	1.355 (3)	C9—C10	1.384 (3)
C2—C13	1.468 (3)	O11—H11	0.83 (3)
C3—O11	1.352 (2)	C13—C18	1.392 (3)
C3—C4	1.449 (3)	C13—C14	1.397 (3)
C4—O12	1.237 (2)	C14—C15	1.379 (3)
C4—C9	1.454 (3)	C14—H14	0.9300
C5—C6	1.367 (3)	C15—C16	1.360 (3)
C5—C9	1.403 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—F19	1.358 (2)
C6—C7	1.392 (3)	C16—C17	1.368 (3)
C6—H6	0.9300	C17—C18	1.378 (3)
C7—C8	1.369 (3)	C17—H17	0.9300
C7—H7	0.9300	C18—H18	0.9300
C10—O1—C2	121.01 (15)	C5—C9—C4	122.85 (18)
C3—C2—O1	120.12 (18)	O1—C10—C9	122.00 (17)
C3—C2—C13	129.15 (18)	O1—C10—C8	116.41 (17)
O1—C2—C13	110.73 (16)	C9—C10—C8	121.58 (19)
O11—C3—C2	120.13 (19)	C3—O11—H11	109 (2)
O11—C3—C4	117.82 (17)	C18—C13—C14	117.60 (18)
C2—C3—C4	122.04 (18)	C18—C13—C2	123.34 (17)
O12—C4—C3	121.08 (19)	C14—C13—C2	119.05 (18)
O12—C4—C9	123.13 (19)	C15—C14—C13	121.43 (19)
C3—C4—C9	115.79 (17)	C15—C14—H14	119.3
C6—C5—C9	120.73 (19)	C13—C14—H14	119.3
C6—C5—H5	119.6	C16—C15—C14	118.73 (19)
C9—C5—H5	119.6	C16—C15—H15	120.6
C5—C6—C7	119.7 (2)	C14—C15—H15	120.6
C5—C6—H6	120.1	F19—C16—C15	118.55 (19)
C7—C6—H6	120.1	F19—C16—C17	119.32 (19)
C8—C7—C6	120.9 (2)	C15—C16—C17	122.1 (2)
C8—C7—H7	119.5	C16—C17—C18	119.08 (19)
C6—C7—H7	119.5	C16—C17—H17	120.5
C7—C8—C10	118.86 (19)	C18—C17—H17	120.5
C7—C8—H8	120.6	C17—C18—C13	121.04 (18)
C10—C8—H8	120.6	C17—C18—H18	119.5
C10—C9—C5	118.14 (18)	C13—C18—H18	119.5
C10—C9—C4	119.01 (18)
C10—O1—C2—C3	1.5 (3)	C5—C9—C10—O1	179.34 (19)
C10—O1—C2—C13	−177.75 (18)	C4—C9—C10—O1	−1.9 (3)
O1—C2—C3—O11	−179.95 (19)	C5—C9—C10—C8	−1.0 (3)
C13—C2—C3—O11	−0.8 (4)	C4—C9—C10—C8	177.8 (2)
O1—C2—C3—C4	−1.4 (3)	C7—C8—C10—O1	179.6 (2)
C13—C2—C3—C4	177.7 (2)	C7—C8—C10—C9	0.0 (4)
O11—C3—C4—O12	−1.9 (3)	C3—C2—C13—C18	11.1 (4)
C2—C3—C4—O12	179.5 (2)	O1—C2—C13—C18	−169.68 (19)
O11—C3—C4—C9	178.3 (2)	C3—C2—C13—C14	−167.8 (2)
C2—C3—C4—C9	−0.3 (3)	O1—C2—C13—C14	11.4 (3)
C9—C5—C6—C7	−1.3 (4)	C18—C13—C14—C15	−0.4 (3)
C5—C6—C7—C8	0.2 (4)	C2—C13—C14—C15	178.6 (2)
C6—C7—C8—C10	0.4 (4)	C13—C14—C15—C16	0.0 (4)
C6—C5—C9—C10	1.7 (3)	C14—C15—C16—F19	179.7 (2)
C6—C5—C9—C4	−177.0 (2)	C14—C15—C16—C17	0.4 (4)
O12—C4—C9—C10	−177.9 (2)	F19—C16—C17—C18	−179.6 (2)
C3—C4—C9—C10	1.9 (3)	C15—C16—C17—C18	−0.3 (4)
O12—C4—C9—C5	0.8 (4)	C16—C17—C18—C13	−0.1 (4)
C3—C4—C9—C5	−179.4 (2)	C14—C13—C18—C17	0.5 (3)
C2—O1—C10—C9	0.2 (3)	C2—C13—C18—C17	−178.5 (2)
C2—O1—C10—C8	−179.50 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O12	0.83 (3)	2.28 (3)	2.722 (2)	113 (3)
O11—H11···O12i	0.83 (3)	2.02 (3)	2.761 (2)	149 (3)

X	I	J	I···J	X···J	X—I···J
C16	F19	Cg1ii	3.888 (2)	3.642 (2)	69.5 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11⋯O12	0.83 (3)	2.28 (3)	2.722 (2)	113 (3)
O11—H11⋯O12i	0.83 (3)	2.02 (3)	2.761 (2)	149 (3)

Symmetry code: (i) .