1-(3,4-Dihydroxy­phen­yl)-2-(4-fluoro­phen­yl)ethanone

In the title compound, C₁₄H₁₁FO₃, the dihedral angle between the aromatic rings is 69.11 (8)°. An intra­molecular O—H...O hydrogen bond is present. Inter­molecular O—H...O inter­actions help to establish the packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.145
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   293.000
            Value of melting point given =     0.000
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Doxybenzion derivatives play an important role in organic chemistry (Li et al., 2007; Li et al., 2008). In the title compound, (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The dihedral angle between the least-squares planes of the two benzene rings is 69.11 (8) °. In the crystal, O—H···O hydrogen bonds (Table 1) 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).

S2. Experimental

Pyrocatechol (0.050 mol) and 2-(4-fluorophenyl)acetic acid (0.050 mol) were dissolved into freshly distilled BF₃Et₂O under argon. The mixture was stirred at room temperature and then poured in an ice bath. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with aq. dried (Na₂S₁O₄), and evaporated. The white deposits precipitated were separated from the solvents by filtration. They were washed with aqueous saturated Na₁H₁C₁O₃ twice. The solid was dissolved in acetone (15 ml) and stirred for about 10 min to give a clear solution. After keeping the solution in air for 10 d, colorless blocks of (I) were formed at the bottom of the vesssl on slow evaporation of the solvent.They were collected, washed three times with acetone and dried in a vacuum desiccator using CaCl₂. The compound was isolated in 90% yield.

S3. Refinement

All the H atoms were positioned geometrically (C—H = 0.93–0.96 Å, O—H = 0.82Å) and refined as riding, with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(O).

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids for the non-hydrogen atoms.

1-(3,4-Dihydroxyphenyl)-2-(4-fluorophenyl)ethanone

Crystal data

C14H11FO3	F(000) = 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 = 9–12°
b = 5.9120 (12) Å	µ = 0.11 mm^−1
c = 24.946 (6) Å	T = 293 K
β = 105.33 (3)°	Block, colorless
V = 1161.2 (4) Å^3	0.28 × 0.25 × 0.17 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	2072 independent reflections
Radiation source: fine-focus sealed tube	1452 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω/2θ scans	θmax = 25.2°, θmin = 1.7°
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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0627P)^2 + 0.5485P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2072 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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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···O2^i	0.82	2.16	2.876 (3)	146
O2—H2B···O3^ii	0.82	1.92	2.744 (2)	178

Symmetry codes: (i) −x, −y, −z; (ii) x−1, y, z.