1-(3,4-Dihydroxy-phen-yl)-2-(4-fluoro-phen-yl)ethanone.

In the title compound, C(14)H(11)FO(3), the dihedral angle between the aromatic rings is 69.11 (8)°. An intra-molecular O-H⋯O hydrogen bond is present. Inter-molecular O-H⋯O inter-actions help to establish the packing.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background on deoxy­benzoins, see: Li et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C14H11FO3

M = 246.23

Monoclinic,

a = 8.1640 (16) Å

b = 5.9120 (12) Å

c = 24.946 (6) Å

β = 105.33 (3)°

V = 1161.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 (2) K

0.28 × 0.25 × 0.17 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.970, T max = 0.982

2229 measured reflections

2072 independent reflections

1452 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 1.04

2072 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035733/hb2831sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035733/hb2831Isup2.hkl

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

C14H11FO3	F000 = 512
Mr = 246.23	Dx = 1.408 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.1640 (16) Å	θ = 9–12º
b = 5.9120 (12) Å	µ = 0.11 mm−1
c = 24.946 (6) Å	T = 293 (2) K
β = 105.33 (3)º	Block, colorless
V = 1161.2 (4) Å3	0.28 × 0.25 × 0.17 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2072 independent reflections
Radiation source: fine-focus sealed tube	1452 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 293(2) K	θmax = 25.2º
ω/2θ scans	θmin = 1.7º
Absorption correction: ψ scan(North et al., 1968)	h = −9→0
Tmin = 0.970, Tmax = 0.982	k = −7→0
2229 measured reflections	l = −28→29

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.0627P)2 + 0.5485P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.18 e Å−3
2072 reflections	Δρmin = −0.17 e Å−3
164 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (3)
Secondary atom site location: difference Fourier map

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
C1	0.5159 (3)	0.4835 (4)	0.08518 (10)	0.0502 (6)
C2	0.4714 (3)	0.2980 (4)	0.04986 (10)	0.0536 (7)
H2A	0.5544	0.2229	0.0374	0.064*
C3	0.3067 (3)	0.2257 (4)	0.03341 (11)	0.0533 (6)
C4	0.1810 (3)	0.3396 (4)	0.05140 (10)	0.0496 (6)
C5	0.2243 (3)	0.5232 (5)	0.08571 (11)	0.0609 (7)
H5A	0.1406	0.5990	0.0977	0.073*
C6	0.3901 (3)	0.5969 (5)	0.10269 (12)	0.0622 (8)
H6A	0.4177	0.7224	0.1258	0.075*
C7	0.6960 (3)	0.5566 (4)	0.10307 (10)	0.0502 (6)
C8	0.7428 (3)	0.7480 (5)	0.14453 (12)	0.0636 (8)
H8A	0.6923	0.8862	0.1266	0.076*
H8B	0.6923	0.7179	0.1749	0.076*
C9	0.9297 (3)	0.7876 (4)	0.16843 (10)	0.0496 (6)
C10	1.0273 (3)	0.6323 (4)	0.20441 (11)	0.0543 (7)
H10A	0.9768	0.5008	0.2129	0.065*
C11	1.1974 (3)	0.6678 (5)	0.22796 (12)	0.0614 (7)
H11A	1.2620	0.5620	0.2522	0.074*
C12	1.2691 (3)	0.8598 (5)	0.21518 (13)	0.0640 (8)
C13	1.1793 (4)	1.0184 (5)	0.17977 (13)	0.0693 (8)
H13A	1.2317	1.1486	0.1715	0.083*
C14	1.0083 (4)	0.9806 (5)	0.15645 (12)	0.0624 (7)
H14A	0.9450	1.0872	0.1322	0.075*
F1	1.4375 (2)	0.8958 (4)	0.23816 (10)	0.1039 (7)
O1	0.2648 (2)	0.0477 (4)	−0.00250 (10)	0.0813 (7)
H1A	0.1726	−0.0035	−0.0012	0.122*
O2	0.0199 (2)	0.2558 (3)	0.03311 (8)	0.0615 (5)
H2B	−0.0421	0.3199	0.0493	0.092*
O3	0.8048 (2)	0.4626 (3)	0.08579 (8)	0.0650 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0430 (13)	0.0574 (15)	0.0503 (14)	0.0101 (11)	0.0126 (10)	−0.0043 (12)
C2	0.0470 (14)	0.0553 (15)	0.0637 (16)	0.0095 (12)	0.0240 (12)	−0.0087 (13)
C3	0.0513 (14)	0.0511 (15)	0.0610 (15)	0.0044 (12)	0.0208 (12)	−0.0110 (13)
C4	0.0426 (13)	0.0552 (15)	0.0528 (14)	0.0084 (11)	0.0157 (11)	0.0012 (12)
C5	0.0429 (14)	0.0747 (19)	0.0676 (17)	0.0135 (13)	0.0190 (12)	−0.0202 (15)
C6	0.0477 (14)	0.0707 (18)	0.0689 (17)	0.0087 (13)	0.0169 (12)	−0.0199 (15)
C7	0.0424 (12)	0.0580 (16)	0.0503 (14)	0.0099 (12)	0.0127 (11)	−0.0033 (12)
C8	0.0495 (14)	0.0680 (18)	0.0720 (18)	0.0114 (13)	0.0139 (13)	−0.0164 (15)
C9	0.0475 (13)	0.0477 (14)	0.0550 (15)	0.0049 (11)	0.0163 (11)	−0.0086 (12)
C10	0.0524 (14)	0.0447 (14)	0.0690 (17)	−0.0029 (12)	0.0216 (12)	0.0032 (13)
C11	0.0513 (15)	0.0593 (17)	0.0721 (18)	0.0063 (13)	0.0137 (13)	0.0068 (14)
C12	0.0458 (14)	0.0609 (17)	0.087 (2)	−0.0100 (13)	0.0207 (14)	−0.0153 (16)
C13	0.075 (2)	0.0485 (16)	0.093 (2)	−0.0114 (15)	0.0380 (17)	−0.0034 (16)
C14	0.0721 (18)	0.0514 (16)	0.0657 (18)	0.0113 (14)	0.0216 (14)	0.0065 (14)
F1	0.0526 (10)	0.0961 (14)	0.157 (2)	−0.0212 (10)	0.0171 (11)	−0.0227 (14)
O1	0.0564 (11)	0.0761 (14)	0.1190 (18)	−0.0081 (10)	0.0364 (11)	−0.0460 (13)
O2	0.0454 (9)	0.0655 (12)	0.0780 (12)	0.0031 (9)	0.0241 (8)	−0.0133 (10)
O3	0.0458 (10)	0.0736 (13)	0.0791 (13)	0.0107 (9)	0.0226 (9)	−0.0201 (10)

C1—C6	1.391 (3)	C8—H8A	0.9700
C1—C2	1.393 (3)	C8—H8B	0.9700
C1—C7	1.483 (3)	C9—C14	1.380 (4)
C2—C3	1.366 (3)	C9—C10	1.380 (3)
C2—H2A	0.9300	C10—C11	1.374 (3)
C3—O1	1.365 (3)	C10—H10A	0.9300
C3—C4	1.397 (3)	C11—C12	1.354 (4)
C4—O2	1.366 (3)	C11—H11A	0.9300
C4—C5	1.369 (4)	C12—F1	1.359 (3)
C5—C6	1.378 (3)	C12—C13	1.362 (4)
C5—H5A	0.9300	C13—C14	1.381 (4)
C6—H6A	0.9300	C13—H13A	0.9300
C7—O3	1.219 (3)	C14—H14A	0.9300
C7—C8	1.512 (4)	O1—H1A	0.8200
C8—C9	1.503 (3)	O2—H2B	0.8200
C6—C1—C2	119.2 (2)	C9—C8—H8B	108.3
C6—C1—C7	121.4 (2)	C7—C8—H8B	108.3
C2—C1—C7	119.4 (2)	H8A—C8—H8B	107.4
C3—C2—C1	120.5 (2)	C14—C9—C10	118.0 (2)
C3—C2—H2A	119.8	C14—C9—C8	121.6 (2)
C1—C2—H2A	119.8	C10—C9—C8	120.3 (2)
O1—C3—C2	119.6 (2)	C11—C10—C9	121.4 (2)
O1—C3—C4	120.3 (2)	C11—C10—H10A	119.3
C2—C3—C4	120.1 (2)	C9—C10—H10A	119.3
O2—C4—C5	124.3 (2)	C12—C11—C10	118.6 (3)
O2—C4—C3	116.2 (2)	C12—C11—H11A	120.7
C5—C4—C3	119.5 (2)	C10—C11—H11A	120.7
C4—C5—C6	120.9 (2)	C11—C12—F1	119.0 (3)
C4—C5—H5A	119.6	C11—C12—C13	122.6 (3)
C6—C5—H5A	119.6	F1—C12—C13	118.5 (3)
C5—C6—C1	119.9 (3)	C12—C13—C14	118.2 (3)
C5—C6—H6A	120.1	C12—C13—H13A	120.9
C1—C6—H6A	120.1	C14—C13—H13A	120.9
O3—C7—C1	121.2 (2)	C9—C14—C13	121.2 (3)
O3—C7—C8	120.5 (2)	C9—C14—H14A	119.4
C1—C7—C8	118.3 (2)	C13—C14—H14A	119.4
C9—C8—C7	115.7 (2)	C3—O1—H1A	109.5
C9—C8—H8A	108.3	C4—O2—H2B	109.5
C7—C8—H8A	108.3
C6—C1—C2—C3	−1.2 (4)	C2—C1—C7—C8	−175.8 (2)
C7—C1—C2—C3	179.1 (2)	O3—C7—C8—C9	−8.8 (4)
C1—C2—C3—O1	178.1 (2)	C1—C7—C8—C9	169.9 (2)
C1—C2—C3—C4	0.9 (4)	C7—C8—C9—C14	112.3 (3)
O1—C3—C4—O2	2.9 (4)	C7—C8—C9—C10	−69.3 (3)
C2—C3—C4—O2	−179.9 (2)	C14—C9—C10—C11	0.3 (4)
O1—C3—C4—C5	−177.5 (3)	C8—C9—C10—C11	−178.2 (2)
C2—C3—C4—C5	−0.3 (4)	C9—C10—C11—C12	−0.1 (4)
O2—C4—C5—C6	179.6 (3)	C10—C11—C12—F1	−179.8 (3)
C3—C4—C5—C6	0.0 (4)	C10—C11—C12—C13	−0.3 (4)
C4—C5—C6—C1	−0.4 (4)	C11—C12—C13—C14	0.3 (5)
C2—C1—C6—C5	1.0 (4)	F1—C12—C13—C14	179.9 (3)
C7—C1—C6—C5	−179.4 (3)	C10—C9—C14—C13	−0.2 (4)
C6—C1—C7—O3	−176.9 (3)	C8—C9—C14—C13	178.3 (2)
C2—C1—C7—O3	2.8 (4)	C12—C13—C14—C9	−0.1 (4)
C6—C1—C7—C8	4.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	2.28	2.690 (2)	111
O1—H1A···O2i	0.82	2.16	2.876 (3)	146
O2—H2B···O3ii	0.82	1.92	2.744 (2)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	2.28	2.690 (2)	111
O1—H1A⋯O2i	0.82	2.16	2.876 (3)	146
O2—H2B⋯O3ii	0.82	1.92	2.744 (2)	178

Symmetry codes: (i) ; (ii) .