3-(4-tert-Butyl­phen­yl)-1-(4-fluoro­phen­yl)-3-hydroxy­prop-2-en-1-one

Zheng, C.; Wang, D.; Fan, L.

doi:10.1107/S1600536808042372

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o150

doi:10.1107/S1600536808042372

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3-(4-tert-Butylphenyl)-1-(4-fluorophenyl)-3-hydroxyprop-2-en-1-one

Chunyang Zheng,^a ^* Dunjia Wang ^b and Ling Fan ^b

^aHubei Key Laboratory of Bioanalytical Techniques, Hubei Normal University, Huangshi 435002, People's Republic of China, and ^bCollege of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, People's Republic of China
^*Correspondence e-mail: zcy800204@163.com

(Received 5 December 2008; accepted 12 December 2008; online 17 December 2008)

The title molecule, C₁₉H₁₉FO₂, exits in the enol form with a dihedral angle of 33.06 (8)° between the two benzene rings. The molecular conformation is stabilized in part by an intramolecular 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_r = 298.34
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.131
S = 1.00
3099 reflections
205 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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)

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 ).

Supporting information

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

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

checkCIF report

Comment top

1,3-Diketones are interesting due to their enolic tautomeric forms and their ability to form strong intermolecular or intramolecular hydrogen bonds (Bertolasi et al., 1991; Vila et al., 1991). They are used widely in the chemistry of metallocomplexes (Baskar et al., 2005; Bassett et al., 2004; Jang et al., 2006; Soldatov et al., 2003). The title compound (I) (Fig. 1), is in the enol form stabilized by an intramolecular O-H···O hydrogen bond (see Table 1).

Related literature top

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 top

1-(4-fluorophenyl)ethanone (1.38 g, 0.01 mol), methyl 4-tert-butylbenzoate (1.92 g, 0.01 mol), NaNH₂ (0.78 g, 0.02 mol) and dry ether (60 ml) were placed into round bottom flask. The mixture was stirred for 6 h at room temperature under a blanket of nitrogen, acidified with dilute hydrochloric acid, and stirring was continued until all solids dissolved. The ether layer was separated and washed with saturated NaHCO₃ solution, dried over anhydrous Na₂SO₄ and was removed by evaporation. The residual solid was recrystallized from ethanol solution to give the title compound (I) (yield 1.78 g, 59.6%, m.p. 388 K). Crystals suitable for X-ray diffraction were grown by slow evaporation of a CHCl₃—EtOH (1:4) solution of the title compound at room temperature.

Computing details top

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

Figures top

Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a intramolecular hydrogen bond.

3-(4-tert-Butylphenyl)-1-(4-fluorophenyl)-3-hydroxyprop-2-en-1-one top

Crystal data top

C₁₉H₁₉FO₂	F(000) = 632
M_r = 298.34	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.07P)²] where P = (F_o² + 2F_c²)/3
3099 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₁₉FO₂	V = 1584.3 (3) Å³
M_r = 298.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8349 (12) Å	µ = 0.09 mm⁻¹
b = 10.0163 (13) Å	T = 298 K
c = 16.232 (2) Å	0.20 × 0.10 × 0.10 mm
β = 97.788 (2)°

Data collection top

Bruker SMART CCD diffractometer	3099 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2199 reflections with I > 2σ(I)
T_min = 0.993, T_max = 0.995	R_int = 0.074
12039 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.17 e Å⁻³
3099 reflections	Δρ_min = −0.19 e Å⁻³
205 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉FO₂
M_r	298.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.8349 (12), 10.0163 (13), 16.232 (2)
β (°)	97.788 (2)
V (Å³)	1584.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.993, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	12039, 3099, 2199
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.131, 1.00
No. of reflections	3099
No. of parameters	205
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

The authors are grateful to Hubei Normal University for financial support.

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