1-(3,4-Dihy-droxy-phen-yl)hexan-1-one.

In the title compound, C(12)H(16)O(3), 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 hexa-none are inclined at an angle 8.5 (2)° with respect to each other. In the crystal, inter-molecular O-H⋯O hydrogen bonds join the mol-ecules 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 = 208.25

Triclinic,

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[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.218

S = 1.00

2321 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.30 e Å−3

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.

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

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

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

C12H16O3	Z = 2
Mr = 208.25	F(000) = 224
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1157P)2 + 0.059P] where P = (Fo2 + 2Fc2)/3
2321 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.30 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	0.2119 (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)

	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)

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

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

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) ; (ii) .