1-(3,4-Dihy­droxy­phen­yl)hexan-1-one

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.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.065
• wR factor = 0.218
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.14
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         17
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         21

Alert level G
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large.       0.12

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with O—H = 0.82 Å and C—H = 0.93, 0.96 and 0.97 Å for the aromatic, CH₃ and CH₂ types H atoms, respectively. U_iso = 1.2U_eq(parent atoms) were assigned for aromatic and CH₂ type H-atoms and 1.5U_eq(parent atoms) for OH and CH₃ type H-atoms.

Computing details

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

	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

Crystal data

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) Å^3

Data collection

Bruker SMART APEX CCD diffractometer	2321 independent reflections
Radiation source: fine-focus sealed tube	1219 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.218	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1157P)^2 + 0.059P] where P = (Fo^2 + 2Fc^2)/3
2321 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.82	2.11	2.828 (3)	147
O1—H1A···O3^ii	0.82	1.93	2.749 (2)	176

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