3-(4-tert-Butyl-phen-yl)-1-(4-fluoro-phen-yl)-3-hydroxy-prop-2-en-1-one.

The title mol-ecule, C(19)H(19)FO(2), exits in the enol form with a dihedral angle of 33.06 (8)° between the two benzene rings. The mol-ecular conformation is stabilized in part by an intra-molecular O-H⋯O hydrogen bond.

Related literature

For background information on 1,3-diketones, see: Baskar & Roesky (2005 ▶); Bassett et al. (2004 ▶); Bertolasi et al. (1991 ▶); Jang et al. (2006 ▶); Soldatov et al. (2003 ▶); Vila et al. (1991 ▶).

Experimental

Crystal data

C19H19FO2

M = 298.34

Monoclinic,

a = 9.8349 (12) Å

b = 10.0163 (13) Å

c = 16.232 (2) Å

β = 97.788 (2)°

V = 1584.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.993, T max = 0.995

12039 measured reflections

3099 independent reflections

2199 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.131

S = 1.00

3099 reflections

205 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042372/lh2743sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042372/lh2743Isup2.hkl

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

C19H19FO2	F(000) = 632
Mr = 298.34	Dx = 1.251 Mg m−3
Monoclinic, P21/n	Melting point: 388 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.8349 (12) Å	Cell parameters from 3223 reflections
b = 10.0163 (13) Å	θ = 2.3–22.9°
c = 16.232 (2) Å	µ = 0.09 mm−1
β = 97.788 (2)°	T = 298 K
V = 1584.3 (3) Å3	Block, colorless
Z = 4	0.20 × 0.10 × 0.10 mm

Bruker SMART CCD diffractometer	3099 independent reflections
Radiation source: fine-focus sealed tube	2199 reflections with I > 2σ(I)
graphite	Rint = 0.074
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.993, Tmax = 0.995	k = −12→12
12039 measured reflections	l = −19→19

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
3099 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−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
C1	0.12996 (18)	0.09274 (19)	−0.07276 (10)	0.0599 (5)
C2	0.0803 (2)	0.2198 (2)	−0.08119 (10)	0.0666 (5)
H2	0.0522	0.2559	−0.1335	0.080*
C3	0.07296 (18)	0.29335 (17)	−0.01033 (9)	0.0587 (5)
H3	0.0401	0.3805	−0.0150	0.070*
C4	0.11376 (15)	0.23969 (16)	0.06796 (9)	0.0457 (4)
C5	0.16498 (16)	0.11083 (17)	0.07303 (9)	0.0545 (4)
H5	0.1943	0.0741	0.1250	0.065*
C6	0.17340 (17)	0.03602 (18)	0.00290 (10)	0.0596 (5)
H6	0.2076	−0.0506	0.0068	0.071*
C7	0.09992 (16)	0.32242 (16)	0.14225 (9)	0.0491 (4)
C8	0.11727 (16)	0.27023 (16)	0.22333 (9)	0.0499 (4)
H8	0.1464	0.1824	0.2321	0.060*
C9	0.09179 (16)	0.34703 (16)	0.29012 (9)	0.0498 (4)
C10	0.09963 (16)	0.29479 (16)	0.37555 (9)	0.0475 (4)
C11	0.01481 (18)	0.34617 (16)	0.42948 (10)	0.0561 (4)
H11	−0.0459	0.4148	0.4118	0.067*
C12	0.01961 (17)	0.29659 (17)	0.50883 (10)	0.0565 (4)
H12	−0.0396	0.3319	0.5432	0.068*
C13	0.10956 (15)	0.19580 (15)	0.53959 (9)	0.0464 (4)
C14	0.19521 (17)	0.14742 (17)	0.48502 (9)	0.0557 (4)
H14	0.2580	0.0808	0.5032	0.067*
C15	0.19034 (17)	0.19472 (17)	0.40495 (9)	0.0541 (4)
H15	0.2488	0.1589	0.3702	0.065*
C16	0.11634 (16)	0.14446 (16)	0.62880 (9)	0.0512 (4)
C17	−0.02548 (19)	0.1488 (2)	0.65807 (11)	0.0744 (6)
H17A	−0.0544	0.2400	0.6614	0.112*
H17B	−0.0205	0.1080	0.7119	0.112*
H17C	−0.0903	0.1012	0.6193	0.112*
C18	0.2134 (2)	0.2360 (2)	0.68505 (10)	0.0774 (6)
H18A	0.3020	0.2364	0.6664	0.116*
H18B	0.2221	0.2039	0.7412	0.116*
H18C	0.1770	0.3250	0.6827	0.116*
C19	0.1691 (2)	0.00150 (18)	0.63681 (12)	0.0791 (6)
H19A	0.1140	−0.0541	0.5973	0.119*
H19B	0.1639	−0.0305	0.6920	0.119*
H19C	0.2628	−0.0010	0.6262	0.119*
F1	0.13561 (14)	0.01881 (12)	−0.14199 (6)	0.0933 (4)
O1	0.06597 (13)	0.44469 (12)	0.12968 (7)	0.0671 (4)
O2	0.05431 (14)	0.47163 (12)	0.27994 (8)	0.0720 (4)
H2A	0.050 (2)	0.485 (2)	0.2088 (15)	0.108*

	U11	U22	U33	U12	U13	U23
C1	0.0655 (12)	0.0679 (12)	0.0478 (9)	0.0042 (9)	0.0136 (8)	−0.0004 (8)
C2	0.0872 (14)	0.0695 (13)	0.0436 (9)	0.0131 (10)	0.0110 (8)	0.0131 (8)
C3	0.0709 (12)	0.0531 (10)	0.0526 (10)	0.0069 (9)	0.0105 (8)	0.0105 (8)
C4	0.0383 (9)	0.0509 (10)	0.0480 (9)	−0.0008 (7)	0.0060 (6)	0.0057 (7)
C5	0.0546 (10)	0.0619 (11)	0.0458 (9)	0.0075 (8)	0.0026 (7)	0.0083 (8)
C6	0.0628 (12)	0.0584 (11)	0.0574 (10)	0.0130 (9)	0.0080 (8)	0.0037 (8)
C7	0.0445 (9)	0.0480 (10)	0.0540 (9)	−0.0026 (7)	0.0035 (7)	0.0054 (7)
C8	0.0547 (10)	0.0466 (10)	0.0475 (9)	0.0040 (8)	0.0040 (7)	0.0024 (7)
C9	0.0493 (10)	0.0455 (10)	0.0525 (9)	−0.0028 (7)	−0.0003 (7)	−0.0013 (7)
C10	0.0484 (9)	0.0456 (9)	0.0468 (8)	−0.0007 (7)	0.0004 (7)	−0.0062 (7)
C11	0.0625 (11)	0.0490 (10)	0.0560 (10)	0.0152 (8)	0.0049 (8)	0.0000 (7)
C12	0.0612 (11)	0.0559 (11)	0.0537 (10)	0.0124 (9)	0.0128 (8)	−0.0052 (8)
C13	0.0465 (9)	0.0443 (9)	0.0475 (8)	−0.0021 (7)	0.0028 (7)	−0.0069 (7)
C14	0.0547 (10)	0.0603 (11)	0.0507 (9)	0.0163 (8)	0.0017 (7)	0.0021 (7)
C15	0.0531 (10)	0.0615 (11)	0.0480 (9)	0.0132 (8)	0.0075 (7)	−0.0049 (7)
C16	0.0502 (10)	0.0554 (10)	0.0471 (9)	−0.0006 (8)	0.0029 (7)	−0.0021 (7)
C17	0.0699 (13)	0.0938 (15)	0.0614 (11)	−0.0013 (11)	0.0153 (9)	0.0105 (10)
C18	0.0857 (14)	0.0914 (15)	0.0515 (10)	−0.0224 (12)	−0.0039 (9)	−0.0023 (9)
C19	0.1093 (17)	0.0651 (13)	0.0644 (12)	0.0161 (12)	0.0167 (11)	0.0115 (9)
F1	0.1407 (12)	0.0884 (9)	0.0527 (6)	0.0260 (7)	0.0201 (6)	−0.0074 (5)
O1	0.0956 (10)	0.0484 (7)	0.0566 (7)	0.0054 (7)	0.0083 (6)	0.0085 (5)
O2	0.1083 (11)	0.0459 (7)	0.0598 (8)	0.0109 (7)	0.0044 (7)	−0.0007 (5)

C1—F1	1.3532 (19)	C11—H11	0.9300
C1—C2	1.364 (3)	C12—C13	1.390 (2)
C1—C6	1.368 (2)	C12—H12	0.9300
C2—C3	1.376 (2)	C13—C14	1.390 (2)
C2—H2	0.9300	C13—C16	1.530 (2)
C3—C4	1.388 (2)	C14—C15	1.378 (2)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.384 (2)	C15—H15	0.9300
C4—C7	1.485 (2)	C16—C19	1.523 (2)
C5—C6	1.375 (2)	C16—C18	1.533 (2)
C5—H5	0.9300	C16—C17	1.534 (2)
C6—H6	0.9300	C17—H17A	0.9600
C7—O1	1.2784 (19)	C17—H17B	0.9600
C7—C8	1.405 (2)	C17—H17C	0.9600
C8—C9	1.380 (2)	C18—H18A	0.9600
C8—H8	0.9300	C18—H18B	0.9600
C9—O2	1.3054 (19)	C18—H18C	0.9600
C9—C10	1.474 (2)	C19—H19A	0.9600
C10—C15	1.383 (2)	C19—H19B	0.9600
C10—C11	1.387 (2)	C19—H19C	0.9600
C11—C12	1.375 (2)	O2—H2A	1.16 (2)
F1—C1—C2	118.81 (15)	C14—C13—C12	115.83 (14)
F1—C1—C6	118.39 (16)	C14—C13—C16	122.26 (14)
C2—C1—C6	122.81 (16)	C12—C13—C16	121.89 (14)
C1—C2—C3	118.32 (15)	C15—C14—C13	122.32 (15)
C1—C2—H2	120.8	C15—C14—H14	118.8
C3—C2—H2	120.8	C13—C14—H14	118.8
C2—C3—C4	121.11 (16)	C14—C15—C10	120.86 (15)
C2—C3—H3	119.4	C14—C15—H15	119.6
C4—C3—H3	119.4	C10—C15—H15	119.6
C5—C4—C3	118.25 (14)	C19—C16—C13	111.57 (14)
C5—C4—C7	123.03 (13)	C19—C16—C18	109.51 (15)
C3—C4—C7	118.72 (14)	C13—C16—C18	107.85 (13)
C6—C5—C4	121.43 (14)	C19—C16—C17	108.31 (15)
C6—C5—H5	119.3	C13—C16—C17	111.03 (13)
C4—C5—H5	119.3	C18—C16—C17	108.51 (15)
C1—C6—C5	118.07 (16)	C16—C17—H17A	109.5
C1—C6—H6	121.0	C16—C17—H17B	109.5
C5—C6—H6	121.0	H17A—C17—H17B	109.5
O1—C7—C8	120.13 (14)	C16—C17—H17C	109.5
O1—C7—C4	117.12 (13)	H17A—C17—H17C	109.5
C8—C7—C4	122.71 (14)	H17B—C17—H17C	109.5
C9—C8—C7	121.11 (15)	C16—C18—H18A	109.5
C9—C8—H8	119.4	C16—C18—H18B	109.5
C7—C8—H8	119.4	H18A—C18—H18B	109.5
O2—C9—C8	120.78 (14)	C16—C18—H18C	109.5
O2—C9—C10	115.86 (14)	H18A—C18—H18C	109.5
C8—C9—C10	123.32 (15)	H18B—C18—H18C	109.5
C15—C10—C11	117.77 (15)	C16—C19—H19A	109.5
C15—C10—C9	122.06 (14)	C16—C19—H19B	109.5
C11—C10—C9	120.17 (15)	H19A—C19—H19B	109.5
C12—C11—C10	120.64 (15)	C16—C19—H19C	109.5
C12—C11—H11	119.7	H19A—C19—H19C	109.5
C10—C11—H11	119.7	H19B—C19—H19C	109.5
C11—C12—C13	122.56 (15)	C7—O1—H2A	101.2 (10)
C11—C12—H12	118.7	C7—O1—H2A	101.2 (10)
C13—C12—H12	118.7	C9—O2—H2A	102.1 (11)
F1—C1—C2—C3	178.96 (17)	O2—C9—C10—C11	29.4 (2)
C6—C1—C2—C3	−0.5 (3)	C8—C9—C10—C11	−148.40 (16)
C1—C2—C3—C4	−0.5 (3)	C15—C10—C11—C12	−1.3 (3)
C2—C3—C4—C5	1.3 (3)	C9—C10—C11—C12	178.87 (15)
C2—C3—C4—C7	−178.35 (16)	C10—C11—C12—C13	1.2 (3)
C3—C4—C5—C6	−1.2 (2)	C11—C12—C13—C14	0.0 (3)
C7—C4—C5—C6	178.49 (15)	C11—C12—C13—C16	178.28 (15)
F1—C1—C6—C5	−178.81 (15)	C12—C13—C14—C15	−0.9 (3)
C2—C1—C6—C5	0.6 (3)	C16—C13—C14—C15	−179.20 (15)
C4—C5—C6—C1	0.2 (3)	C13—C14—C15—C10	0.7 (3)
C5—C4—C7—O1	172.32 (15)	C11—C10—C15—C14	0.4 (3)
C3—C4—C7—O1	−8.0 (2)	C9—C10—C15—C14	−179.79 (15)
C5—C4—C7—C8	−10.2 (2)	C14—C13—C16—C19	−27.3 (2)
C3—C4—C7—C8	169.45 (15)	C12—C13—C16—C19	154.50 (16)
O1—C7—C8—C9	3.2 (2)	C14—C13—C16—C18	93.01 (19)
C4—C7—C8—C9	−174.20 (14)	C12—C13—C16—C18	−85.19 (19)
C7—C8—C9—O2	−1.8 (2)	C14—C13—C16—C17	−148.23 (16)
C7—C8—C9—C10	175.89 (14)	C12—C13—C16—C17	33.6 (2)
O2—C9—C10—C15	−150.37 (16)	C8—C7—O1—H2A	−3.3 (9)
C8—C9—C10—C15	31.8 (2)	C4—C7—O1—H2A	174.2 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	1.16 (2)	1.38 (2)	2.4720 (16)	154 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	1.16 (2)	1.38 (2)	2.4720 (16)	154 (2)