1-[2-Hy-droxy-4-(prop-2-yn-1-yl-oxy)phen-yl]ethanone.

In the title compound, C11H10O3, there is an intra-molecular O-H⋯O hydrogen bond generating an S(6) ring motif. The O atom of the hy-droxy group deviates by 0.0200 (1) Å from the benzene ring to which it is attached. The propyne group is almost linear, the C-C C angle being 177.83 (15)°, and is almost coplanar with the benzene ring; the C-C-O-C torsion angle being only -1.1 (2)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming infinite C(11) chains running parallel to [103]. These chains are linked by a pair of C-H⋯O hydrogen bonds, enclosing R 2 (2)(8) inversion dimers, forming a corrugated two-dimensional network lying parallel to (103).

Related literature

For the biological activity of benzaldehyde derivatives, see: Zhao et al. (2007 ▶); Ley & Bertram (2001 ▶); Delogu et al. (2010 ▶). For a related structure, see: Esakkiammal et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H10O3

M = 190.19

Monoclinic,

a = 4.9975 (2) Å

b = 10.4305 (4) Å

c = 18.8467 (7) Å

β = 97.257 (2)°

V = 974.54 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.968, T max = 0.981

9316 measured reflections

2451 independent reflections

1898 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.130

S = 1.05

2451 reflections

138 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032613/su2668sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032613/su2668Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032613/su2668Isup3.cml

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

C11H10O3	F(000) = 400
Mr = 190.19	Dx = 1.296 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2451 reflections
a = 4.9975 (2) Å	θ = 2.2–28.4°
b = 10.4305 (4) Å	µ = 0.10 mm−1
c = 18.8467 (7) Å	T = 293 K
β = 97.257 (2)°	Block, colourless
V = 974.54 (7) Å3	0.35 × 0.30 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	2451 independent reflections
Radiation source: fine-focus sealed tube	1898 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→6
Tmin = 0.968, Tmax = 0.981	k = −13→13
9316 measured reflections	l = −25→25

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0637P)2 + 0.1394P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2451 reflections	Δρmax = 0.17 e Å−3
138 parameters	Δρmin = −0.21 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (4)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.9425 (3)	0.69719 (11)	0.08613 (7)	0.0455 (3)
C2	0.9120 (2)	0.81055 (10)	0.12463 (6)	0.0421 (3)
C3	1.0579 (3)	0.91806 (11)	0.10720 (6)	0.0475 (3)
H3	1.0417	0.9941	0.1320	0.057*
C4	1.2229 (3)	0.91474 (11)	0.05494 (7)	0.0506 (3)
H4	1.3186	0.9874	0.0446	0.061*
C5	1.2467 (3)	0.80135 (11)	0.01728 (6)	0.0446 (3)
C6	1.1094 (3)	0.69245 (11)	0.03266 (6)	0.0468 (3)
H6	1.1283	0.6169	0.0076	0.056*
C7	0.7340 (3)	0.81464 (12)	0.18017 (6)	0.0485 (3)
C8	0.7041 (4)	0.93600 (15)	0.22030 (9)	0.0632 (4)
H8A	0.595 (4)	0.9292 (18)	0.2554 (11)	0.095*
H8B	0.648 (4)	1.005 (2)	0.1896 (10)	0.095*
H8C	0.872 (4)	0.9636 (19)	0.2446 (10)	0.095*
C9	1.4462 (3)	0.69606 (12)	−0.07557 (7)	0.0527 (3)
H9A	1.2727	0.6639	−0.0972	0.063*
H9B	1.5342	0.6298	−0.0449	0.063*
C10	1.6120 (3)	0.73056 (13)	−0.13064 (7)	0.0546 (3)
C11	1.7405 (3)	0.75594 (16)	−0.17657 (8)	0.0680 (4)
H11	1.8424	0.7761	−0.2130	0.082*
O1	0.8072 (2)	0.58946 (8)	0.09853 (6)	0.0691 (4)
H1	0.7187	0.6017	0.1317	0.104*
O2	0.6074 (2)	0.71799 (10)	0.19459 (5)	0.0624 (3)
O3	1.4107 (2)	0.80891 (8)	−0.03494 (5)	0.0574 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0506 (7)	0.0372 (5)	0.0508 (6)	−0.0075 (5)	0.0149 (5)	0.0001 (4)
C2	0.0460 (6)	0.0395 (5)	0.0418 (5)	−0.0015 (5)	0.0098 (5)	0.0009 (4)
C3	0.0570 (7)	0.0372 (5)	0.0501 (6)	−0.0056 (5)	0.0140 (5)	−0.0060 (4)
C4	0.0595 (8)	0.0385 (6)	0.0569 (7)	−0.0126 (5)	0.0196 (6)	−0.0035 (5)
C5	0.0457 (7)	0.0431 (6)	0.0472 (6)	−0.0071 (5)	0.0149 (5)	−0.0022 (4)
C6	0.0531 (7)	0.0370 (5)	0.0531 (6)	−0.0072 (5)	0.0177 (6)	−0.0073 (4)
C7	0.0549 (8)	0.0484 (6)	0.0438 (6)	0.0027 (5)	0.0127 (5)	0.0033 (5)
C8	0.0781 (11)	0.0589 (8)	0.0572 (8)	0.0039 (8)	0.0270 (8)	−0.0065 (6)
C9	0.0567 (8)	0.0491 (7)	0.0558 (7)	−0.0084 (6)	0.0200 (6)	−0.0096 (5)
C10	0.0569 (8)	0.0544 (7)	0.0553 (7)	−0.0037 (6)	0.0179 (6)	−0.0085 (6)
C11	0.0790 (11)	0.0666 (9)	0.0649 (8)	−0.0040 (8)	0.0339 (8)	−0.0095 (7)
O1	0.0912 (8)	0.0423 (5)	0.0835 (7)	−0.0214 (5)	0.0488 (6)	−0.0082 (4)
O2	0.0751 (7)	0.0571 (6)	0.0612 (6)	−0.0077 (5)	0.0334 (5)	0.0043 (4)
O3	0.0673 (6)	0.0475 (5)	0.0644 (6)	−0.0165 (4)	0.0354 (5)	−0.0110 (4)

C1—O1	1.3469 (14)	C7—O2	1.2384 (15)
C1—C6	1.3879 (16)	C7—C8	1.4918 (18)
C1—C2	1.4056 (16)	C8—H8A	0.91 (2)
C2—C3	1.3991 (16)	C8—H8B	0.94 (2)
C2—C7	1.4573 (16)	C8—H8C	0.95 (2)
C3—C4	1.3627 (17)	C9—O3	1.4275 (14)
C3—H3	0.9300	C9—C10	1.4529 (18)
C4—C5	1.3920 (16)	C9—H9A	0.9700
C4—H4	0.9300	C9—H9B	0.9700
C5—O3	1.3602 (14)	C10—C11	1.1712 (19)
C5—C6	1.3765 (16)	C11—H11	0.9300
C6—H6	0.9300	O1—H1	0.8200
O1—C1—C6	117.20 (10)	O2—C7—C8	119.53 (12)
O1—C1—C2	121.51 (11)	C2—C7—C8	119.89 (11)
C6—C1—C2	121.27 (10)	C7—C8—H8A	114.1 (12)
C3—C2—C1	117.34 (11)	C7—C8—H8B	112.2 (12)
C3—C2—C7	121.92 (10)	H8A—C8—H8B	110.2 (17)
C1—C2—C7	120.75 (10)	C7—C8—H8C	111.3 (12)
C4—C3—C2	122.03 (10)	H8A—C8—H8C	104.4 (16)
C4—C3—H3	119.0	H8B—C8—H8C	103.9 (17)
C2—C3—H3	119.0	O3—C9—C10	107.45 (10)
C3—C4—C5	119.24 (10)	O3—C9—H9A	110.2
C3—C4—H4	120.4	C10—C9—H9A	110.2
C5—C4—H4	120.4	O3—C9—H9B	110.2
O3—C5—C6	124.19 (10)	C10—C9—H9B	110.2
O3—C5—C4	114.68 (10)	H9A—C9—H9B	108.5
C6—C5—C4	121.13 (10)	C11—C10—C9	177.83 (15)
C5—C6—C1	118.99 (10)	C10—C11—H11	180.0
C5—C6—H6	120.5	C1—O1—H1	109.5
C1—C6—H6	120.5	C5—O3—C9	117.87 (9)
O2—C7—C2	120.59 (11)
O1—C1—C2—C3	−179.06 (12)	C4—C5—C6—C1	0.8 (2)
C6—C1—C2—C3	−0.40 (19)	O1—C1—C6—C5	178.60 (12)
O1—C1—C2—C7	0.7 (2)	C2—C1—C6—C5	−0.1 (2)
C6—C1—C2—C7	179.39 (12)	C3—C2—C7—O2	−179.90 (12)
C1—C2—C3—C4	0.3 (2)	C1—C2—C7—O2	0.3 (2)
C7—C2—C3—C4	−179.52 (12)	C3—C2—C7—C8	−0.1 (2)
C2—C3—C4—C5	0.4 (2)	C1—C2—C7—C8	−179.89 (13)
C3—C4—C5—O3	178.37 (12)	C6—C5—O3—C9	−1.1 (2)
C3—C4—C5—C6	−0.9 (2)	C4—C5—O3—C9	179.62 (12)
O3—C5—C6—C1	−178.44 (12)	C10—C9—O3—C5	175.97 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.83	2.5551 (14)	146
C4—H4···O3i	0.93	2.54	3.4609 (16)	172
C11—H11···O2ii	0.93	2.32	3.2337 (18)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.83	2.5551 (14)	146
C4—H4⋯O3i	0.93	2.54	3.4609 (16)	172
C11—H11⋯O2ii	0.93	2.32	3.2337 (18)	168

Symmetry codes: (i) ; (ii) .