1-(5-Acetyl-2-hy­droxy­phen­yl)ethanone

Hübscher, J.; Izotova, L.; Talipov, S.; Eissmann, F.; Weber, E.

doi:10.1107/S1600536811020423

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1622

doi:10.1107/S1600536811020423

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1-(5-Acetyl-2-hydroxyphenyl)ethanone

Jörg Hübscher,^a Lidiya Izotova,^b Samat Talipov,^b ^* Frank Eissmann ^a and Edwin Weber ^a

^aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany, and ^bInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek Street 83, 100125 Tashkent, Uzbekistan
^*Correspondence e-mail: samat_talipov@yahoo.com

(Received 4 May 2011; accepted 28 May 2011; online 11 June 2011)

The crystal structure of the title compound, C₁₀H₁₀O₃, is characterized by classical intramolecular hydrogen bonding. The hydroxy group is disordered over two positions (77 and 23%). The crystal structure is stabilized via π–π [3.5986 (1) Å] and weak nonclassical C—H⋯O interactions [3.2797 (15) Å].

Related literature

For hydrogen bonding, see: Desiraju & Steiner (1999 ). For π–π interactions, see: Janiak (2000 ). For the antifungal activity of the title compound, see: Prats et al. (2007 ).

Experimental

Crystal data

C₁₀H₁₀O₃
M_r = 178.18
Monoclinic, P 2₁ /c
a = 7.1134 (2) Å
b = 10.9260 (3) Å
c = 11.5291 (3) Å
β = 98.485 (2)°
V = 886.25 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 153 K
0.60 × 0.57 × 0.52 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.659, T_max = 0.747
9182 measured reflections
1855 independent reflections
1577 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.123
S = 1.11
1855 reflections
132 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2	0.84	1.78	2.5240 (15)	147
O1A—H1OA⋯O3	0.84	1.58	2.369 (6)	156
C6—H6⋯O3ⁱ	0.95	2.55	3.2797 (15)	134
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020423/rk2275sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020423/rk2275Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020423/rk2275Isup3.cml

checkCIF report

Comment top

The title compound is known for its high antifungal activity (Prats et al., 2007). In the molecule, the hydroxy–group is disordered over two positions [O1—H10 and O1A—H10A with occupancies of 0.769 (3) and 0.231 (3), respectively] related to each other via 180° rotation about the C3–C6 molecule axis. The molecule is almost planar with a maximum derivation from the mean plane of all non hydrogen atoms (RMS = 0.0458) of 0.1185 (14)Å for the methyl atom C8 (Fig. 1). The bond lengths and bond angles of the benzene ring are normal. The carbonyl and the disordered hydroxy–group of the molecule are involved in classical intramolecular H–bonds (O1—H1O···O2, 2.5240 (15)Å, 147.3°; O1A—H1OA···O3 2.369 (6)Å, 155.8°), while no conventional intermolecular hydrogen bond is found in the packing structure. The structure is stabilized via π–π–interactions (Janiak, 2000) involving the neighboring diacylphenol molecules in the stacks - Cg···Cg distance between consecutive molecules is 3.5986 (1)Å, which run in direction of the crystallographic a–axis (Fig. 2). Interaction between these stacks is realised via weak C—H···O interactions (Desiraju & Steiner, 1999) C6—H6···O3ⁱ (3.2797 (15)Å). Symmetry code: (i) -x; y-1/2; -z-1/2.

Related literature top

For hydrogen bonding, see: Desiraju & Steiner (1999). For π–π interactions, see: Janiak (2000). For the antifungal activity of the title compound, see: Prats et al. (2007).

Experimental top

The title compound has been obtained as a by–product during attempted formation of a complex between 2–acetyl–4–ethynylphenol with Co(II) in MeOH solution due to hydrolysis. The prismatic shaped crystals are yellow colored and stable in the air.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title compound with the atom numbring scheme. Displacement ellipsoids are drawn at 40% probability level. Dashed line represents intramolecular H–bond. Only major moiety of disordered hydroxy–group is presented.
	Fig. 2. Packing diagram of the title compound, viewed down the a–axis. The weak hydrogen bonds are shown as dashed lines.

1-(5-Acetyl-2-hydroxyphenyl)ethanone top

Crystal data top

C₁₀H₁₀O₃	F(000) = 376
M_r = 178.18	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5377 reflections
a = 7.1134 (2) Å	θ = 2.6–33.0°
b = 10.9260 (3) Å	µ = 0.10 mm⁻¹
c = 11.5291 (3) Å	T = 153 K
β = 98.485 (2)°	Prism, yellow
V = 886.25 (4) Å³	0.60 × 0.57 × 0.52 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	1855 independent reflections
Radiation source: fine–focus sealed tube	1577 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 26.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
T_min = 0.659, T_max = 0.747	k = −13→13
9182 measured reflections	l = −14→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0664P)² + 0.1717P] where P = (F_o² + 2F_c²)/3
1855 reflections	(Δ/σ)_max < 0.001
132 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₀H₁₀O₃	V = 886.25 (4) Å³
M_r = 178.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1134 (2) Å	µ = 0.10 mm⁻¹
b = 10.9260 (3) Å	T = 153 K
c = 11.5291 (3) Å	0.60 × 0.57 × 0.52 mm
β = 98.485 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1855 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1577 reflections with I > 2σ(I)
T_min = 0.659, T_max = 0.747	R_int = 0.018
9182 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.11	Δρ_max = 0.30 e Å⁻³
1855 reflections	Δρ_min = −0.21 e Å⁻³
132 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
O1	0.36987 (18)	0.74231 (10)	0.01694 (11)	0.0392 (4)	0.769 (3)
H1O	0.4139	0.7335	0.0881	0.059*	0.769 (3)
O1A	0.0897 (7)	1.0538 (5)	−0.2444 (3)	0.0555 (15)	0.231 (3)
H1OA	0.0636	1.1284	−0.2393	0.083*	0.231 (3)
O2	0.46630 (14)	0.80245 (8)	0.22874 (8)	0.0416 (3)
O3	0.05289 (18)	1.25536 (12)	−0.17533 (10)	0.0643 (4)
C1	0.30909 (15)	0.85929 (11)	−0.00259 (10)	0.0301 (3)
H1A	0.3534	0.7780	0.0124	0.036*	0.231 (3)
C2	0.32180 (14)	0.94450 (10)	0.08990 (9)	0.0254 (3)
C3	0.25975 (14)	1.06404 (10)	0.06490 (9)	0.0256 (3)
H3	0.2690	1.1223	0.1267	0.031*
C4	0.18496 (15)	1.09999 (11)	−0.04787 (10)	0.0301 (3)
C5	0.17072 (16)	1.01185 (13)	−0.13782 (10)	0.0354 (3)
H5	0.1177	1.0345	−0.2153	0.042*	0.769 (3)
C6	0.23194 (16)	0.89384 (13)	−0.11574 (10)	0.0361 (3)
H6	0.2216	0.8358	−0.1777	0.043*
C7	0.40012 (16)	0.90573 (11)	0.20988 (10)	0.0301 (3)
C8	0.3997 (2)	0.99274 (13)	0.30966 (11)	0.0432 (3)
H8A	0.4300	0.9484	0.3839	0.065*
H8B	0.2738	1.0303	0.3053	0.065*
H8C	0.4950	1.0567	0.3052	0.065*
C9	0.11948 (17)	1.22703 (13)	−0.07529 (12)	0.0408 (3)
C10	0.1355 (2)	1.31998 (13)	0.02060 (15)	0.0483 (4)
H10A	0.0878	1.3989	−0.0117	0.073*
H10B	0.2690	1.3285	0.0557	0.073*
H10C	0.0603	1.2935	0.0807	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0458 (7)	0.0296 (6)	0.0432 (7)	0.0006 (5)	0.0100 (5)	−0.0058 (5)
O1A	0.056 (3)	0.080 (4)	0.028 (2)	−0.018 (3)	−0.0051 (18)	0.005 (2)
O2	0.0476 (6)	0.0300 (5)	0.0460 (5)	0.0046 (4)	0.0027 (4)	0.0099 (4)
O3	0.0627 (7)	0.0742 (8)	0.0516 (7)	0.0163 (6)	−0.0056 (5)	0.0302 (6)
C1	0.0222 (5)	0.0309 (6)	0.0383 (6)	−0.0045 (4)	0.0082 (4)	−0.0042 (5)
C2	0.0193 (5)	0.0284 (6)	0.0289 (6)	−0.0029 (4)	0.0046 (4)	0.0013 (4)
C3	0.0197 (5)	0.0283 (6)	0.0289 (6)	−0.0016 (4)	0.0034 (4)	0.0022 (4)
C4	0.0188 (5)	0.0392 (7)	0.0318 (6)	−0.0023 (5)	0.0022 (4)	0.0076 (5)
C5	0.0221 (6)	0.0562 (8)	0.0268 (6)	−0.0061 (5)	0.0002 (4)	0.0029 (5)
C6	0.0266 (6)	0.0491 (8)	0.0333 (6)	−0.0083 (5)	0.0062 (5)	−0.0102 (5)
C7	0.0271 (6)	0.0281 (6)	0.0352 (6)	−0.0018 (4)	0.0043 (4)	0.0065 (5)
C8	0.0586 (9)	0.0409 (7)	0.0285 (6)	0.0063 (6)	0.0012 (6)	0.0040 (5)
C9	0.0259 (6)	0.0486 (8)	0.0471 (7)	0.0029 (5)	0.0029 (5)	0.0203 (6)
C10	0.0455 (8)	0.0330 (7)	0.0667 (9)	0.0054 (6)	0.0090 (7)	0.0157 (6)

Geometric parameters (Å, º) top

O1—C1	1.3573 (16)	C4—C5	1.4078 (18)
O1—H1O	0.8400	C4—C9	1.4833 (18)
O1A—C5	1.357 (4)	C5—C6	1.373 (2)
O1A—H1OA	0.8400	C5—H5	0.9500
O2—C7	1.2297 (15)	C6—H6	0.9500
O3—C9	1.2204 (17)	C7—C8	1.4926 (17)
C1—C6	1.3908 (17)	C8—H8A	0.9800
C1—C2	1.4083 (16)	C8—H8B	0.9800
C1—H1A	0.9500	C8—H8C	0.9800
C2—C3	1.3951 (16)	C9—C10	1.493 (2)
C2—C7	1.4751 (15)	C10—H10A	0.9800
C3—C4	1.3870 (15)	C10—H10B	0.9800
C3—H3	0.9500	C10—H10C	0.9800

C1—O1—H1O	109.5	C5—C6—C1	119.96 (11)
C5—O1A—H1OA	109.5	C5—C6—H6	120.0
O1—C1—C6	118.89 (11)	C1—C6—H6	120.0
O1—C1—C2	120.91 (11)	O2—C7—C2	120.74 (11)
C6—C1—C2	120.20 (11)	O2—C7—C8	119.50 (11)
C6—C1—H1A	119.9	C2—C7—C8	119.76 (10)
C2—C1—H1A	119.9	C7—C8—H8A	109.5
C3—C2—C1	118.66 (10)	C7—C8—H8B	109.5
C3—C2—C7	121.78 (10)	H8A—C8—H8B	109.5
C1—C2—C7	119.56 (10)	C7—C8—H8C	109.5
C4—C3—C2	121.65 (11)	H8A—C8—H8C	109.5
C4—C3—H3	119.2	H8B—C8—H8C	109.5
C2—C3—H3	119.2	O3—C9—C4	120.31 (15)
C3—C4—C5	118.21 (11)	O3—C9—C10	120.26 (13)
C3—C4—C9	121.99 (12)	C4—C9—C10	119.43 (11)
C5—C4—C9	119.80 (11)	C9—C10—H10A	109.5
O1A—C5—C6	124.4 (3)	C9—C10—H10B	109.5
O1A—C5—C4	114.2 (3)	H10A—C10—H10B	109.5
C6—C5—C4	121.30 (11)	C9—C10—H10C	109.5
C6—C5—H5	119.3	H10A—C10—H10C	109.5
C4—C5—H5	119.3	H10B—C10—H10C	109.5

O1—C1—C2—C3	179.13 (11)	O1A—C5—C6—C1	−178.5 (3)
C6—C1—C2—C3	−1.47 (16)	C4—C5—C6—C1	0.28 (17)
O1—C1—C2—C7	−0.74 (16)	O1—C1—C6—C5	−179.54 (11)
C6—C1—C2—C7	178.67 (10)	C2—C1—C6—C5	1.04 (17)
C1—C2—C3—C4	0.59 (16)	C3—C2—C7—O2	−174.85 (10)
C7—C2—C3—C4	−179.55 (10)	C1—C2—C7—O2	5.01 (17)
C2—C3—C4—C5	0.69 (16)	C3—C2—C7—C8	4.99 (17)
C2—C3—C4—C9	−179.72 (10)	C1—C2—C7—C8	−175.15 (11)
C3—C4—C5—O1A	177.7 (2)	C3—C4—C9—O3	−179.39 (12)
C9—C4—C5—O1A	−1.9 (3)	C5—C4—C9—O3	0.20 (19)
C3—C4—C5—C6	−1.14 (17)	C3—C4—C9—C10	0.55 (18)
C9—C4—C5—C6	179.26 (11)	C5—C4—C9—C10	−179.86 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.84	1.78	2.5240 (15)	147
O1A—H1OA···O3	0.84	1.58	2.369 (6)	156
C6—H6···O3ⁱ	0.95	2.55	3.2797 (15)	134

Symmetry code: (i) −x, y−1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀O₃
M_r	178.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	7.1134 (2), 10.9260 (3), 11.5291 (3)
β (°)	98.485 (2)
V (Å³)	886.25 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.60 × 0.57 × 0.52

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.659, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	9182, 1855, 1577
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.123, 1.11
No. of reflections	1855
No. of parameters	132
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.84	1.78	2.5240 (15)	147.3
O1A—H1OA···O3	0.84	1.58	2.369 (6)	155.8
C6—H6···O3ⁱ	0.95	2.55	3.2797 (15)	134.2

Symmetry code: (i) −x, y−1/2, −z−1/2.

Acknowledgements

This work was performed within the Cluster of Excellence `Structure Design of Novel High–Performance Materials via Atomic Design and Defect Engineering (ADDE)', which is financially supported by the European Union (European Regional Development Fund) and by the Ministry of Science and Art of Saxony (SMWK). LI is gratefull to DFG for a travel grant.

References

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