Crystal structure of 1-(2,4-dihy-droxy-6-methyl-phen-yl)ethanone.

The title compound, C9H10O3, is a bioactive secondary metabolite, isolated from the endophytic fungus Nodulisporium sp. The compound exhibits an intra-molecular O-H⋯O hydrogen bond between the phenolic H atom and the carbonyl O atom of the adjacent acetyl group. In the crystal, mol-ecules are linked by hydrogen bonds involving the 4-phenolic H atom and a symmetry-related carbonyl O atom of a neighboring mol-ecule, resulting in extended supra-molecular chains along the a-axis direction. Aromatic π-π stacking inter-actions between the nearly parallel benzene rings of adjacent chains [centroid-centroid distance = 3.7478 (8) Å] further stabilize the three-dimensional supra-molecular framework.

Related literature

For biological activities of aceto­phenone derivatives, see: Das & Khosla (2009 ▸); Suzuki et al. (2006 ▸); Tabuchi et al. (2014 ▸). For related structures, see: Azeezaa et al. (2009 ▸); Chakkaravarthi et al. (2007 ▸); Hill et al. (2012 ▸).

Experimental

Crystal data

C9H10O3

M = 166.17

Monoclinic,

a = 7.3570 (3) Å

b = 15.001 (1) Å

c = 7.3180 (5) Å

β = 91.017 (4)°

V = 807.50 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.25 × 0.25 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer

3260 measured reflections

1828 independent reflections

1319 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.150

S = 1.03

1828 reflections

114 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: COLLECT (Nonius, 2000 ▸); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▸); data reduction: DENZO (Otwinowski & Minor, 1997 ▸) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015013468/xu5859sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013468/xu5859Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015013468/xu5859Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015013468/xu5859fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015013468/xu5859fig2.tif

The partial packing diagram shows layers of mol­ecules built up by bifurcated O—H⋯O hydrogen bonds and π–π inter­molecular inter­actions between phenyl rings.

CCDC reference: 1412605

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H10O3	F(000) = 352
Mr = 166.17	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.3570 (3) Å	Cell parameters from 1754 reflections
b = 15.001 (1) Å	θ = 1.0–27.5°
c = 7.3180 (5) Å	µ = 0.10 mm−1
β = 91.017 (4)°	T = 298 K
V = 807.50 (8) Å3	Block, yellow
Z = 4	0.25 × 0.25 × 0.25 mm

Nonius KappaCCD diffractometer	1319 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD scans	h = −9→9
3260 measured reflections	k = −17→19
1828 independent reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.1187P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1828 reflections	Δρmax = 0.22 e Å−3
114 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.06 (2)

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	0.70787 (19)	0.22482 (9)	0.77437 (17)	0.0385 (4)
C2	0.70538 (18)	0.32006 (10)	0.77086 (18)	0.0407 (4)
C3	0.8510 (2)	0.37042 (10)	0.83381 (19)	0.0436 (4)
H3	0.8441	0.4381	0.8326	0.052*
C4	1.00510 (19)	0.32826 (10)	0.89794 (19)	0.0447 (4)
C5	1.0142 (2)	0.23520 (10)	0.9001 (2)	0.0446 (4)
H5	1.1320	0.2021	0.9410	0.053*
C6	0.87053 (19)	0.18331 (10)	0.84171 (17)	0.0416 (4)
C7	0.5457 (2)	0.17763 (10)	0.70990 (19)	0.0456 (4)
C8	0.5184 (3)	0.07921 (13)	0.7285 (3)	0.0776 (6)
H8A	0.6044	0.0483	0.6544	0.116*
H8B	0.3972	0.0640	0.6891	0.116*
H8C	0.5360	0.0622	0.8541	0.116*
O9	0.41657 (15)	0.21912 (7)	0.63688 (18)	0.0588 (4)
O10	0.55972 (15)	0.36627 (7)	0.70969 (17)	0.0552 (4)
H10	0.4830	0.3316	0.6688	0.083*
O11	1.14661 (16)	0.37918 (8)	0.95736 (18)	0.0631 (4)
H11	1.2256	0.3471	1.0026	0.095*
C12	0.9014 (3)	0.08414 (11)	0.8510 (2)	0.0607 (5)
H12A	0.8165	0.0580	0.9335	0.073*
H12B	1.0231	0.0725	0.8940	0.073*
H12C	0.8842	0.0588	0.7315	0.073*

	U11	U22	U33	U12	U13	U23
C1	0.0408 (8)	0.0373 (8)	0.0373 (7)	0.0021 (6)	−0.0033 (6)	0.0009 (5)
C2	0.0384 (7)	0.0409 (8)	0.0426 (7)	0.0061 (6)	−0.0036 (5)	0.0034 (6)
C3	0.0438 (8)	0.0373 (8)	0.0496 (8)	0.0011 (6)	−0.0048 (6)	0.0029 (6)
C4	0.0404 (8)	0.0485 (9)	0.0449 (8)	−0.0015 (6)	−0.0053 (6)	0.0013 (6)
C5	0.0402 (8)	0.0481 (9)	0.0452 (8)	0.0092 (6)	−0.0059 (6)	0.0017 (6)
C6	0.0464 (8)	0.0393 (8)	0.0390 (7)	0.0068 (6)	−0.0027 (6)	0.0024 (5)
C7	0.0462 (8)	0.0469 (9)	0.0436 (8)	−0.0020 (7)	−0.0047 (6)	0.0001 (6)
C8	0.0771 (13)	0.0495 (11)	0.1050 (15)	−0.0156 (9)	−0.0344 (11)	0.0089 (10)
O9	0.0443 (7)	0.0558 (7)	0.0756 (8)	−0.0015 (5)	−0.0172 (5)	0.0004 (5)
O10	0.0447 (7)	0.0420 (6)	0.0782 (8)	0.0077 (5)	−0.0177 (5)	0.0043 (5)
O11	0.0475 (7)	0.0556 (7)	0.0853 (9)	−0.0071 (5)	−0.0213 (6)	0.0027 (6)
C12	0.0671 (11)	0.0429 (9)	0.0717 (11)	0.0126 (8)	−0.0123 (8)	0.0029 (8)

C1—C6	1.4288 (18)	C6—C12	1.506 (2)
C1—C2	1.429 (2)	C7—O9	1.2481 (18)
C1—C7	1.4585 (19)	C7—C8	1.497 (2)
C2—O10	1.3462 (16)	C8—H8A	0.9600
C2—C3	1.3831 (19)	C8—H8B	0.9600
C3—C4	1.374 (2)	C8—H8C	0.9600
C3—H3	1.0170	O10—H10	0.8200
C4—O11	1.3566 (18)	O11—H11	0.8200
C4—C5	1.398 (2)	C12—H12A	0.9600
C5—C6	1.375 (2)	C12—H12B	0.9600
C5—H5	1.0380	C12—H12C	0.9600
C6—C1—C2	116.89 (13)	O9—C7—C1	120.57 (14)
C6—C1—C7	125.12 (13)	O9—C7—C8	115.38 (14)
C2—C1—C7	117.99 (12)	C1—C7—C8	124.04 (14)
O10—C2—C3	115.89 (13)	C7—C8—H8A	109.5
O10—C2—C1	122.05 (13)	C7—C8—H8B	109.5
C3—C2—C1	122.04 (12)	H8A—C8—H8B	109.5
C4—C3—C2	119.47 (14)	C7—C8—H8C	109.5
C4—C3—H3	120.3	H8A—C8—H8C	109.5
C2—C3—H3	120.3	H8B—C8—H8C	109.5
O11—C4—C3	118.31 (14)	C2—O10—H10	109.5
O11—C4—C5	121.49 (13)	C4—O11—H11	109.5
C3—C4—C5	120.19 (13)	C6—C12—H12A	109.5
C6—C5—C4	121.71 (13)	C6—C12—H12B	109.5
C6—C5—H5	116.9	H12A—C12—H12B	109.5
C4—C5—H5	121.4	C6—C12—H12C	109.5
C5—C6—C1	119.68 (13)	H12A—C12—H12C	109.5
C5—C6—C12	115.52 (13)	H12B—C12—H12C	109.5
C1—C6—C12	124.79 (14)
C6—C1—C2—O10	179.79 (12)	C4—C5—C6—C1	0.9 (2)
C7—C1—C2—O10	−0.3 (2)	C4—C5—C6—C12	179.57 (14)
C6—C1—C2—C3	−1.66 (19)	C2—C1—C6—C5	0.41 (19)
C7—C1—C2—C3	178.24 (13)	C7—C1—C6—C5	−179.48 (13)
O10—C2—C3—C4	−179.77 (13)	C2—C1—C6—C12	−178.14 (14)
C1—C2—C3—C4	1.6 (2)	C7—C1—C6—C12	2.0 (2)
C2—C3—C4—O11	179.41 (13)	C6—C1—C7—O9	−172.96 (13)
C2—C3—C4—C5	−0.2 (2)	C2—C1—C7—O9	7.2 (2)
O11—C4—C5—C6	179.36 (14)	C6—C1—C7—C8	8.5 (2)
C3—C4—C5—C6	−1.0 (2)	C2—C1—C7—C8	−171.41 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O9	0.82	1.77	2.4991 (16)	147
O11—H11···O9i	0.82	1.97	2.7843 (16)	173

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O10H10O9	0.82	1.77	2.4991(16)	147
O11H11O9i	0.82	1.97	2.7843(16)	173

Symmetry code: (i) .