1-(3,4-Dihy­droxy­phen­yl)hexan-1-one

Peng, X.-C.; Huang, W.-J.; Wang, X.; Wu, D.-H.; Xiao, Z.-P.

doi:10.1107/S1600536810022555

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1725

doi:10.1107/S1600536810022555

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1-(3,4-Dihydroxyphenyl)hexan-1-one

Xiao-Chun Peng,^a Wei-Jun Huang,^a Xi Wang,^a Dao-Hong Wu ^a and Zhu-Ping Xiao ^a ^*

^aCollege of Chemistry & Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
^*Correspondence e-mail: xiaozhuping2005@163.com

(Received 30 May 2010; accepted 12 June 2010; online 23 June 2010)

In the title compound, C₁₂H₁₆O₃, a fully extened hexyl carbon chain is attached to a benzene ring; the mean planes formed by the atoms in the benzene ring and the hexanone are inclined at an angle 8.5 (2)° with respect to each other. In the crystal, intermolecular O—H⋯O hydrogen bonds join the molecules into an infinite sheet.

Related literature

For the biological activity of alkylcatechols, see: Buu-hoï & Seailles (1955 ); Buu-hoï & Xuong (1961 ); Miller et al. (1938 ); Xiao, Fang et al. (2007 ); Xiao, Xue et al. (2007 ). For related structures, see: Cheng et al. (2009 ); Wang et al. (2009 ).

Experimental

Crystal data

C₁₂H₁₆O₃
M_r = 208.25
Triclinic, $[P \overline 1]$
a = 7.170 (2) Å
b = 8.070 (3) Å
c = 10.634 (4) Å
α = 75.638 (17)°
β = 73.373 (19)°
γ = 88.323 (17)°
V = 570.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.975, T_max = 0.983
3311 measured reflections
2321 independent reflections
1219 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.218
S = 1.00
2321 reflections
139 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	2.29	2.718 (2)	113
O2—H2⋯O1ⁱ	0.82	2.11	2.828 (3)	147
O1—H1A⋯O3ⁱⁱ	0.82	1.93	2.749 (2)	176
Symmetry codes: (i) -x, -y, -z; (ii) x, y-1, z.

Data collection: SMART (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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022555/pv2291sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022555/pv2291Isup2.hkl

checkCIF report

Comment top

Acylcatechols are intermediates in the synthesis of alkycatechols which show significant bactericidal activity (Miller et al., 1938; Xiao, Xue et al., 2007; Xiao, Fang et al., 2007) and possess considerable protective properties against lethal radiations (Buu-hoï & Seailles, 1955; Buu-hoï & Xuong, 1961). Consequently, we have synthesized a series of acylcatechols for bioactivity screening. In this paper, the crystal structure of the title compound has been presented. The crystal structures of compounds related to the title molecule have been reported (Cheng et al., 2009; Wang et al., 2009).

The bond lengths and angles in the title compound (Fig. 1) are unexceptional (Cheng et al., 2009; Wang et al., 2009). The hexyl carbon chain (C7—C12) attached to the phenyl ring is fully extened; the mean-planes formed by the atoms in the phenyl ring and hexanone are inclined at an angle 8.5 (2) ° with respect to each other. The two hydroxyl groups of catechol moiety are involved in an intramolecular hydrogen bond, O2—H2···O1 (Fig. 1). There are two O—H···O type intermolecular hydrogen bonds which stabilize the crystal structure and result in an infinite sheet (Fig. 2 and Tab. 1).

Related literature top

For the biological activity of alkycatechols, see: Buu-hoï & Seailles (1955); Buu-hoï & Xuong (1961); Miller et al. (1938); Xiao, Fang et al. (2007); Xiao, Xue et al. (2007). For related structures, see: Cheng et al. (2009); Wang et al. (2009).

Experimental top

1-(3,4-Dihydroxyphenyl)hexan-1-one was prepared by treating hexanoic acid (1.27 g, 11 mmol) with catechol (1.11 g, 10 mmol) at 348 K for 4 h in boron trifluoride diethyl etherate (20 mL). After cooling, the contents were poured into 150 ml of ice-cold aqueous sodium acetate (10%) with stirring. Then, the mixture was extracted with EtOAc and dried over MgSO₄. After removal of solvent, the crude product was crystalized from EtOAc-petroleum (2:3) to give colorless blocks of the title compound suitable for single-crystal structure determination.

Computing details top

Data collection: SMART (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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atomic-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A two-dimensional sheet formed through intermolecular O—H···O hydrogen bonds.

1-(3,4-Dihydroxyphenyl)hexan-1-one top

Crystal data top

C₁₂H₁₆O₃	Z = 2
M_r = 208.25	F(000) = 224
Triclinic, P1	D_x = 1.212 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.170 (2) Å	Cell parameters from 1104 reflections
b = 8.070 (3) Å	θ = 2.8–25.9°
c = 10.634 (4) Å	µ = 0.09 mm⁻¹
α = 75.638 (17)°	T = 296 K
β = 73.373 (19)°	Block, colorless
γ = 88.323 (17)°	0.30 × 0.24 × 0.20 mm
V = 570.6 (3) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	2321 independent reflections
Radiation source: fine-focus sealed tube	1219 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 26.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.975, T_max = 0.983	k = −10→10
3311 measured reflections	l = −13→13

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.218	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1157P)² + 0.059P] where P = (F_o² + 2F_c²)/3
2321 reflections	(Δ/σ)_max < 0.001
139 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₂H₁₆O₃	γ = 88.323 (17)°
M_r = 208.25	V = 570.6 (3) Å³
Triclinic, P1	Z = 2
a = 7.170 (2) Å	Mo Kα radiation
b = 8.070 (3) Å	µ = 0.09 mm⁻¹
c = 10.634 (4) Å	T = 296 K
α = 75.638 (17)°	0.30 × 0.24 × 0.20 mm
β = 73.373 (19)°

Data collection top

Bruker SMART APEX CCD diffractometer	2321 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1219 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.016
3311 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.218	H-atom parameters constrained
S = 1.00	Δρ_max = 0.27 e Å⁻³
2321 reflections	Δρ_min = −0.30 e Å⁻³
139 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	0.2119 (4)	0.3836 (3)	0.1188 (3)	0.0558 (7)
H1	0.1472	0.4851	0.1048	0.067*
C2	0.1460 (4)	0.2413 (3)	0.0920 (3)	0.0565 (7)
C3	0.2425 (4)	0.0894 (3)	0.1127 (3)	0.0540 (7)
C4	0.4023 (4)	0.0824 (3)	0.1594 (3)	0.0627 (8)
H4	0.4670	−0.0191	0.1730	0.075*
C5	0.4682 (4)	0.2247 (3)	0.1864 (3)	0.0616 (8)
H5	0.5768	0.2183	0.2183	0.074*
C6	0.3743 (4)	0.3774 (3)	0.1665 (3)	0.0518 (7)
C7	0.4394 (4)	0.5320 (3)	0.1971 (3)	0.0562 (7)
C8	0.6048 (4)	0.5200 (3)	0.2579 (3)	0.0661 (8)
H8A	0.7211	0.4946	0.1932	0.079*
H8B	0.5762	0.4244	0.3376	0.079*
C9	0.6490 (5)	0.6798 (4)	0.2985 (4)	0.0746 (9)
H9A	0.6914	0.7730	0.2176	0.090*
H9B	0.5302	0.7121	0.3565	0.090*
C10	0.8016 (5)	0.6562 (4)	0.3708 (4)	0.0818 (10)
H10A	0.9216	0.6285	0.3109	0.098*
H10B	0.7617	0.5589	0.4489	0.098*
C11	0.8435 (6)	0.8093 (5)	0.4187 (4)	0.1014 (12)
H11A	0.7271	0.8344	0.4833	0.122*
H11B	0.8805	0.9087	0.3422	0.122*
C12	1.0097 (8)	0.7713 (6)	0.4859 (5)	0.1353 (17)
H12A	0.9851	0.6605	0.5486	0.203*
H12B	1.0161	0.8568	0.5333	0.203*
H12C	1.1311	0.7729	0.4174	0.203*
O1	0.1692 (3)	−0.0474 (2)	0.0840 (2)	0.0678 (6)
H1A	0.2286	−0.1328	0.1064	0.102*
O2	−0.0156 (3)	0.2520 (2)	0.0467 (3)	0.0810 (7)
H2	−0.0279	0.1659	0.0214	0.121*
O3	0.3591 (3)	0.6667 (2)	0.1739 (2)	0.0714 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0566 (15)	0.0368 (13)	0.0788 (19)	0.0104 (11)	−0.0238 (14)	−0.0190 (12)
C2	0.0543 (15)	0.0413 (13)	0.081 (2)	0.0079 (11)	−0.0261 (14)	−0.0214 (13)
C3	0.0582 (16)	0.0348 (12)	0.0747 (19)	0.0041 (11)	−0.0228 (14)	−0.0200 (12)
C4	0.0632 (17)	0.0372 (13)	0.100 (2)	0.0137 (12)	−0.0371 (16)	−0.0240 (14)
C5	0.0594 (16)	0.0436 (14)	0.094 (2)	0.0102 (12)	−0.0393 (16)	−0.0209 (14)
C6	0.0511 (14)	0.0376 (13)	0.0712 (18)	0.0060 (11)	−0.0207 (13)	−0.0186 (12)
C7	0.0621 (17)	0.0395 (14)	0.0705 (18)	0.0052 (12)	−0.0218 (14)	−0.0172 (12)
C8	0.0774 (19)	0.0475 (15)	0.085 (2)	0.0059 (13)	−0.0375 (17)	−0.0205 (14)
C9	0.083 (2)	0.0506 (16)	0.102 (2)	0.0032 (15)	−0.0437 (19)	−0.0220 (16)
C10	0.089 (2)	0.073 (2)	0.092 (2)	−0.0020 (18)	−0.034 (2)	−0.0281 (18)
C11	0.117 (3)	0.097 (3)	0.105 (3)	−0.017 (2)	−0.035 (2)	−0.047 (2)
C12	0.145 (4)	0.132 (4)	0.162 (4)	−0.001 (3)	−0.073 (4)	−0.064 (3)
O1	0.0716 (13)	0.0383 (9)	0.1094 (16)	0.0105 (9)	−0.0433 (12)	−0.0283 (10)
O2	0.0760 (13)	0.0531 (11)	0.147 (2)	0.0214 (10)	−0.0673 (14)	−0.0462 (12)
O3	0.0833 (14)	0.0400 (10)	0.1058 (16)	0.0155 (9)	−0.0440 (12)	−0.0271 (10)

Geometric parameters (Å, º) top

C1—C2	1.376 (3)	C8—H8B	0.9700
C1—C6	1.392 (4)	C9—C10	1.491 (4)
C1—H1	0.9300	C9—H9A	0.9700
C2—O2	1.369 (3)	C9—H9B	0.9700
C2—C3	1.391 (3)	C10—C11	1.515 (4)
C3—C4	1.368 (3)	C10—H10A	0.9700
C3—O1	1.371 (3)	C10—H10B	0.9700
C4—C5	1.377 (4)	C11—C12	1.543 (6)
C4—H4	0.9300	C11—H11A	0.9700
C5—C6	1.385 (3)	C11—H11B	0.9700
C5—H5	0.9300	C12—H12A	0.9600
C6—C7	1.484 (3)	C12—H12B	0.9600
C7—O3	1.220 (3)	C12—H12C	0.9600
C7—C8	1.495 (4)	O1—H1A	0.8200
C8—C9	1.526 (4)	O2—H2	0.8200
C8—H8A	0.9700

C2—C1—C6	120.8 (2)	C10—C9—C8	113.4 (3)
C2—C1—H1	119.6	C10—C9—H9A	108.9
C6—C1—H1	119.6	C8—C9—H9A	108.9
O2—C2—C1	119.0 (2)	C10—C9—H9B	108.9
O2—C2—C3	121.2 (2)	C8—C9—H9B	108.9
C1—C2—C3	119.7 (2)	H9A—C9—H9B	107.7
C4—C3—O1	123.5 (2)	C9—C10—C11	115.1 (3)
C4—C3—C2	119.8 (2)	C9—C10—H10A	108.5
O1—C3—C2	116.7 (2)	C11—C10—H10A	108.5
C3—C4—C5	120.5 (2)	C9—C10—H10B	108.5
C3—C4—H4	119.8	C11—C10—H10B	108.5
C5—C4—H4	119.8	H10A—C10—H10B	107.5
C4—C5—C6	120.7 (2)	C10—C11—C12	110.0 (3)
C4—C5—H5	119.7	C10—C11—H11A	109.7
C6—C5—H5	119.7	C12—C11—H11A	109.7
C5—C6—C1	118.5 (2)	C10—C11—H11B	109.7
C5—C6—C7	122.0 (2)	C12—C11—H11B	109.7
C1—C6—C7	119.5 (2)	H11A—C11—H11B	108.2
O3—C7—C6	120.8 (2)	C11—C12—H12A	109.5
O3—C7—C8	120.3 (2)	C11—C12—H12B	109.5
C6—C7—C8	119.0 (2)	H12A—C12—H12B	109.5
C7—C8—C9	115.3 (2)	C11—C12—H12C	109.5
C7—C8—H8A	108.4	H12A—C12—H12C	109.5
C9—C8—H8A	108.4	H12B—C12—H12C	109.5
C7—C8—H8B	108.4	C3—O1—H1A	109.5
C9—C8—H8B	108.4	C2—O2—H2	109.5
H8A—C8—H8B	107.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	2.29	2.718 (2)	113
O2—H2···O1ⁱ	0.82	2.11	2.828 (3)	147
O1—H1A···O3ⁱⁱ	0.82	1.93	2.749 (2)	176

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆O₃
M_r	208.25
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.170 (2), 8.070 (3), 10.634 (4)
α, β, γ (°)	75.638 (17), 73.373 (19), 88.323 (17)
V (Å³)	570.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	3311, 2321, 1219
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.218, 1.00
No. of reflections	2321
No. of parameters	139
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.30

Computer programs: SMART (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
O2—H2···O1	0.82	2.29	2.718 (2)	113
O2—H2···O1ⁱ	0.82	2.11	2.828 (3)	147
O1—H1A···O3ⁱⁱ	0.82	1.93	2.749 (2)	176

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

Acknowledgements

The work was financed by grants (Project 06 J J2067) from the Natural Science Foundation of Hunan Province, China, and by the Scientific Research Fund of Hunan Provincial Education Department (Project 09B083) of China.

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