2-(2-Hy-droxy-propan-2-yl)-6-(prop-2-yn-yloxy)-1-benzofuran-3(2H)-one.

In the title compound, C14H14O4, the prop-2-yn-yloxy O-C-C C plane [maximum deviation = 0.0116 (12) Å] forms a dihedral angle of 78.44 (9)° with the benzofuran-3(2H)-one ring system. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming a tape along the a-axis direction. C-H⋯O inter-actions are observed between the tapes.

Related literature

For background to the development of hybrid drug candidates against tuberculosis, malaria and cancer, see: Morphy et al. (2004 ▶). For details of the synthesis of the title compound, see: Hoogendoorn et al. (2011 ▶).

Experimental

Crystal data

C14H14O4

M = 246.25

Triclinic,

a = 5.4199 (2) Å

b = 9.0785 (3) Å

c = 12.3555 (4) Å

α = 85.758 (2)°

β = 80.455 (2)°

γ = 81.829 (2)°

V = 592.65 (4) Å3

Z = 2

Cu Kα radiation

μ = 0.84 mm−1

T = 100 K

0.39 × 0.11 × 0.11 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.736, T max = 0.913

10266 measured reflections

1983 independent reflections

1888 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.082

S = 1.03

1983 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812045606/is5212sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045606/is5212Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045606/is5212Isup3.cml

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

C14H14O4	Z = 2
Mr = 246.25	F(000) = 260
Triclinic, P1	Dx = 1.38 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 5.4199 (2) Å	Cell parameters from 4605 reflections
b = 9.0785 (3) Å	θ = 4.9–66.1°
c = 12.3555 (4) Å	µ = 0.84 mm−1
α = 85.758 (2)°	T = 100 K
β = 80.455 (2)°	Needle, colourless
γ = 81.829 (2)°	0.39 × 0.11 × 0.11 mm
V = 592.65 (4) Å3

Bruker APEX DUO 4K CCD diffractometer	1983 independent reflections
Incoatec Quazar Multilayer Mirror monochromator	1888 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1	Rint = 0.025
φ and ω scans	θmax = 66.3°, θmin = 4.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −4→6
Tmin = 0.736, Tmax = 0.913	k = −10→10
10266 measured reflections	l = −14→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0364P)2 + 0.2704P] where P = (Fo2 + 2Fc2)/3
1983 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. Analytical data: 1H NMR (CDCl3, 400 MHZ): δ 7.55 (d, 1H), 6.69 (s, 1H), 6.66 (s, 1H), 4.74 (s, 2H), 4.36 (s, 1H), 3.26 (s, 1H), 2.58 (s, 1H), 1.33 (s, 3H), 1.18 (s, 3H); 13C NMR (CDCl3, 400 MHZ): δ 199.0, 175.0, 166.2, 125.4, 115.5, 112.1, 97.4, 89.8, 72.3, 56.3, 25.9, 23.9.The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 5 s/frame. A total of 4558 frames were collected with a frame width of 1° covering up to θ = 66.28° with 95.2% completeness accomplished.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.2006 (3)	0.84616 (15)	0.02726 (11)	0.0261 (3)
H1	0.1077	0.8209	−0.0259	0.031*
C2	0.3167 (2)	0.87773 (14)	0.09371 (10)	0.0223 (3)
C3	0.4670 (2)	0.91785 (15)	0.17253 (10)	0.0223 (3)
H3A	0.6387	0.9299	0.1339	0.027*
H3B	0.3894	1.0148	0.2026	0.027*
C4	0.2852 (2)	0.80294 (13)	0.34321 (10)	0.0172 (3)
C5	0.0548 (2)	0.89754 (13)	0.34541 (10)	0.0189 (3)
H5	0.0309	0.9688	0.2866	0.023*
C6	−0.1355 (2)	0.88612 (13)	0.43326 (10)	0.0180 (3)
H6	−0.2907	0.9504	0.4362	0.022*
C7	−0.0975 (2)	0.77883 (13)	0.51799 (10)	0.0167 (3)
C8	0.1301 (2)	0.68501 (13)	0.51207 (10)	0.0164 (3)
C9	0.3268 (2)	0.69443 (13)	0.42660 (10)	0.0177 (3)
H9	0.4822	0.6306	0.4246	0.021*
C10	−0.2529 (2)	0.73992 (13)	0.61999 (10)	0.0173 (3)
C11	−0.0979 (2)	0.60810 (13)	0.67327 (10)	0.0177 (3)
H11	−0.1864	0.5181	0.6763	0.021*
C12	−0.0406 (2)	0.62882 (13)	0.78842 (10)	0.0183 (3)
C13	0.1469 (2)	0.49897 (14)	0.82127 (11)	0.0237 (3)
H13A	0.3049	0.4962	0.7693	0.036*
H13B	0.0765	0.4055	0.8203	0.036*
H13C	0.1802	0.5115	0.8954	0.036*
C14	−0.2814 (2)	0.64049 (15)	0.87195 (10)	0.0233 (3)
H14A	−0.2438	0.6637	0.9432	0.035*
H14B	−0.3504	0.5455	0.8793	0.035*
H14C	−0.4052	0.7198	0.8472	0.035*
O1	0.05931 (15)	0.76695 (9)	0.78783 (7)	0.0193 (2)
H	0.2022	0.7612	0.7486	0.029*
O2	0.14038 (15)	0.58334 (9)	0.59873 (7)	0.0187 (2)
O3	0.48574 (16)	0.80822 (10)	0.26152 (7)	0.0215 (2)
O4	−0.46595 (15)	0.79629 (10)	0.65811 (7)	0.0215 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0272 (7)	0.0300 (7)	0.0206 (7)	−0.0034 (6)	−0.0019 (5)	−0.0033 (5)
C2	0.0241 (7)	0.0221 (6)	0.0176 (6)	−0.0009 (5)	0.0036 (5)	0.0003 (5)
C3	0.0251 (7)	0.0247 (7)	0.0167 (6)	−0.0065 (5)	−0.0002 (5)	0.0016 (5)
C4	0.0184 (6)	0.0194 (6)	0.0144 (6)	−0.0047 (5)	−0.0010 (5)	−0.0043 (5)
C5	0.0222 (6)	0.0188 (6)	0.0161 (6)	−0.0023 (5)	−0.0050 (5)	−0.0006 (5)
C6	0.0173 (6)	0.0185 (6)	0.0187 (6)	−0.0003 (5)	−0.0047 (5)	−0.0033 (5)
C7	0.0163 (6)	0.0180 (6)	0.0166 (6)	−0.0030 (4)	−0.0035 (5)	−0.0038 (5)
C8	0.0204 (6)	0.0151 (6)	0.0150 (6)	−0.0034 (5)	−0.0049 (5)	−0.0024 (4)
C9	0.0171 (6)	0.0186 (6)	0.0175 (6)	−0.0002 (5)	−0.0034 (5)	−0.0038 (5)
C10	0.0166 (6)	0.0197 (6)	0.0174 (6)	−0.0050 (5)	−0.0041 (5)	−0.0041 (5)
C11	0.0161 (6)	0.0187 (6)	0.0176 (6)	−0.0037 (5)	0.0003 (5)	−0.0010 (5)
C12	0.0184 (6)	0.0195 (6)	0.0171 (6)	−0.0046 (5)	−0.0021 (5)	0.0010 (5)
C13	0.0242 (7)	0.0239 (7)	0.0220 (7)	−0.0013 (5)	−0.0043 (5)	0.0033 (5)
C14	0.0214 (7)	0.0302 (7)	0.0175 (6)	−0.0045 (5)	−0.0013 (5)	0.0024 (5)
O1	0.0183 (5)	0.0207 (5)	0.0188 (4)	−0.0044 (3)	−0.0002 (3)	−0.0024 (3)
O2	0.0204 (5)	0.0182 (4)	0.0156 (4)	0.0009 (3)	−0.0002 (3)	0.0006 (3)
O3	0.0197 (5)	0.0272 (5)	0.0155 (4)	−0.0010 (3)	0.0005 (3)	0.0015 (3)
O4	0.0154 (5)	0.0279 (5)	0.0203 (5)	−0.0017 (3)	−0.0014 (3)	−0.0012 (4)

C1—C2	1.187 (2)	C9—H9	0.95
C1—H1	0.95	C10—O4	1.2264 (15)
C2—C3	1.4647 (18)	C10—C11	1.5338 (17)
C3—O3	1.4339 (15)	C11—O2	1.4561 (14)
C3—H3A	0.99	C11—C12	1.5359 (17)
C3—H3B	0.99	C11—H11	1
C4—O3	1.3586 (14)	C12—O1	1.4339 (14)
C4—C9	1.3952 (17)	C12—C14	1.5198 (17)
C4—C5	1.4092 (18)	C12—C13	1.5206 (17)
C5—C6	1.3767 (17)	C13—H13A	0.98
C5—H5	0.95	C13—H13B	0.98
C6—C7	1.3968 (17)	C13—H13C	0.98
C6—H6	0.95	C14—H14A	0.98
C7—C8	1.3906 (17)	C14—H14B	0.98
C7—C10	1.4454 (17)	C14—H14C	0.98
C8—O2	1.3640 (15)	O1—H	0.84
C8—C9	1.3777 (17)
C2—C1—H1	180	C7—C10—C11	105.72 (10)
C1—C2—C3	177.97 (13)	O2—C11—C10	105.17 (9)
O3—C3—C2	112.50 (10)	O2—C11—C12	108.40 (9)
O3—C3—H3A	109.1	C10—C11—C12	116.67 (10)
C2—C3—H3A	109.1	O2—C11—H11	108.8
O3—C3—H3B	109.1	C10—C11—H11	108.8
C2—C3—H3B	109.1	C12—C11—H11	108.8
H3A—C3—H3B	107.8	O1—C12—C14	106.41 (10)
O3—C4—C9	113.90 (10)	O1—C12—C13	110.61 (10)
O3—C4—C5	123.96 (11)	C14—C12—C13	110.22 (10)
C9—C4—C5	122.14 (11)	O1—C12—C11	109.16 (9)
C6—C5—C4	119.68 (11)	C14—C12—C11	110.66 (10)
C6—C5—H5	120.2	C13—C12—C11	109.74 (10)
C4—C5—H5	120.2	C12—C13—H13A	109.5
C5—C6—C7	119.14 (11)	C12—C13—H13B	109.5
C5—C6—H6	120.4	H13A—C13—H13B	109.5
C7—C6—H6	120.4	C12—C13—H13C	109.5
C8—C7—C6	119.71 (11)	H13A—C13—H13C	109.5
C8—C7—C10	107.37 (10)	H13B—C13—H13C	109.5
C6—C7—C10	132.92 (11)	C12—C14—H14A	109.5
O2—C8—C9	123.28 (11)	C12—C14—H14B	109.5
O2—C8—C7	113.74 (10)	H14A—C14—H14B	109.5
C9—C8—C7	122.98 (11)	C12—C14—H14C	109.5
C8—C9—C4	116.33 (11)	H14A—C14—H14C	109.5
C8—C9—H9	121.8	H14B—C14—H14C	109.5
C4—C9—H9	121.8	C12—O1—H	109.5
O4—C10—C7	128.78 (11)	C8—O2—C11	107.95 (9)
O4—C10—C11	125.50 (11)	C4—O3—C3	118.88 (9)
O3—C4—C5—C6	−178.39 (10)	O4—C10—C11—O2	−179.31 (10)
C9—C4—C5—C6	1.43 (18)	C7—C10—C11—O2	1.55 (12)
C4—C5—C6—C7	−1.02 (17)	O4—C10—C11—C12	−59.16 (16)
C5—C6—C7—C8	−0.40 (17)	C7—C10—C11—C12	121.70 (11)
C5—C6—C7—C10	178.94 (12)	O2—C11—C12—O1	68.57 (11)
C6—C7—C8—O2	−178.57 (10)	C10—C11—C12—O1	−49.84 (13)
C10—C7—C8—O2	1.93 (14)	O2—C11—C12—C14	−174.64 (9)
C6—C7—C8—C9	1.55 (18)	C10—C11—C12—C14	66.94 (13)
C10—C7—C8—C9	−177.94 (11)	O2—C11—C12—C13	−52.79 (12)
O2—C8—C9—C4	178.99 (10)	C10—C11—C12—C13	−171.21 (10)
C7—C8—C9—C4	−1.15 (18)	C9—C8—O2—C11	178.98 (10)
O3—C4—C9—C8	179.49 (10)	C7—C8—O2—C11	−0.89 (13)
C5—C4—C9—C8	−0.34 (17)	C10—C11—O2—C8	−0.46 (12)
C8—C7—C10—O4	178.84 (12)	C12—C11—O2—C8	−125.94 (10)
C6—C7—C10—O4	−0.6 (2)	C9—C4—O3—C3	−178.56 (10)
C8—C7—C10—C11	−2.06 (12)	C5—C4—O3—C3	1.28 (17)
C6—C7—C10—C11	178.53 (12)	C2—C3—O3—C4	−76.90 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H···O4i	0.84	2.01	2.8328 (12)	167
C1—H1···O1ii	0.95	2.45	3.3283 (16)	154
C5—H5···O1iii	0.95	2.52	3.3809 (15)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H⋯O4i	0.84	2.01	2.8328 (12)	167
C1—H1⋯O1ii	0.95	2.45	3.3283 (16)	154
C5—H5⋯O1iii	0.95	2.52	3.3809 (15)	152

Symmetry codes: (i) ; (ii) ; (iii) .