5-Hy-droxy-7-phenyl-5-(prop-2-yn-1-yl)-5,6-dihydro-1-benzofuran-2(4H)-one monohydrate.

In the title compound, C(17)H(14)O(3)·H(2)O, the six-membered ring, which adopts a half-chair conformation, makes a dihedral angle of 24.3 (2)° with the phenyl ring. In the crystal, the components are linked by O-H⋯O hydrogen bonds involving the water mol-ecule, and the hy-droxy and carbonyl groups of the organic compound. These inter-actions form a square-like supra-molecular synthon unit which propagates as chains parallel to the crystallographic b axis. A C-H⋯O interaction also occurs.

Related literature

For related literature about the cited reactions, see: Bassetti et al. (2005 ▶); Beck et al. (2001 ▶); Liu et al. (2006 ▶); Ma & Gu (2005 ▶); Rudler et al. (2004 ▶).

Experimental

Crystal data

C17H14O3·H2O

M = 284.30

Monoclinic,

a = 9.1585 (2) Å

b = 9.2160 (3) Å

c = 17.4628 (5) Å

β = 91.145 (2)°

V = 1473.65 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ▶) T min = 0.982, T max = 0.983

5821 measured reflections

3360 independent reflections

2251 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.191

S = 1.14

3360 reflections

195 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.69 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: SIR2004 (Burla et al., 2005 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028400/zq2046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028400/zq2046Isup2.hkl

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

C17H14O3·H2O	F(000) = 600
Mr = 284.30	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3327 reflections
a = 9.1585 (2) Å	θ = 1.0–27.5°
b = 9.2160 (3) Å	µ = 0.09 mm−1
c = 17.4628 (5) Å	T = 293 K
β = 91.145 (2)°	Prismatic, colourless
V = 1473.65 (7) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Nonius KappaCCD diffractometer	3360 independent reflections
Radiation source: Enraf–Nonius FR590	2251 reflections with I > 2σ(I)
horizonally mounted graphite crystal	Rint = 0.028
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.2°
CCD rotation images, thick slices scans	h = −11→11
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	k = −11→11
Tmin = 0.982, Tmax = 0.983	l = −22→22
5821 measured reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.1074P)2] where P = (Fo2 + 2Fc2)/3
3360 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.50 e Å−3
3 restraints	Δρmin = −0.69 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
O10	0.09705 (15)	−0.35189 (15)	0.55947 (8)	0.0309 (4)
H10	0.0938	−0.3890	0.5168	0.046*
O21	0.07886 (17)	−0.41878 (17)	0.40700 (9)	0.0371 (4)
H21A	0.0106	−0.5029	0.4127	0.108 (13)*
H21B	0.0326	−0.3487	0.3699	0.080 (10)*
O1	0.15674 (17)	0.09639 (15)	0.59615 (7)	0.0299 (4)
O14	0.0447 (2)	0.21621 (17)	0.69040 (8)	0.0424 (5)
C16	0.2016 (2)	0.0987 (2)	0.42937 (12)	0.0332 (5)
H16	0.1281	0.1288	0.4617	0.040*
C5	0.2133 (2)	−0.0433 (2)	0.58766 (11)	0.0257 (5)
C9	0.2434 (2)	−0.2746 (2)	0.66557 (11)	0.0283 (5)
H9A	0.1778	−0.3283	0.6981	0.034*
H9B	0.3403	−0.2774	0.6889	0.034*
C11	0.3067 (2)	−0.4999 (2)	0.58931 (12)	0.0334 (5)
H11A	0.2479	−0.5566	0.6239	0.040*
H11B	0.2965	−0.5428	0.5388	0.040*
C8	0.2462 (2)	−0.3443 (2)	0.58623 (11)	0.0267 (5)
C2	0.1017 (3)	0.1045 (2)	0.66926 (11)	0.0319 (5)
C12	0.4598 (3)	−0.5102 (2)	0.61430 (12)	0.0327 (5)
C4	0.1930 (2)	−0.1211 (2)	0.65843 (10)	0.0260 (5)
C6	0.2752 (2)	−0.0953 (2)	0.52416 (11)	0.0244 (5)
C17	0.2193 (3)	0.1677 (3)	0.35963 (12)	0.0408 (6)
H17	0.1571	0.2432	0.3454	0.049*
C7	0.3324 (2)	−0.2498 (2)	0.53073 (11)	0.0281 (5)
H7A	0.4338	−0.2469	0.5478	0.034*
H7B	0.3288	−0.2945	0.4804	0.034*
C15	0.2936 (2)	−0.0165 (2)	0.45162 (11)	0.0264 (5)
C20	0.4029 (2)	−0.0591 (2)	0.40115 (11)	0.0325 (5)
H20	0.4645	−0.1357	0.4143	0.039*
C3	0.1265 (2)	−0.0318 (2)	0.70729 (11)	0.0308 (5)
H3	0.1009	−0.0542	0.7572	0.037*
C19	0.4203 (3)	0.0118 (3)	0.33181 (13)	0.0391 (6)
H19	0.4938	−0.0171	0.2991	0.047*
C18	0.3288 (3)	0.1249 (3)	0.31113 (12)	0.0412 (6)
H18	0.3409	0.1723	0.2647	0.049*
C13	0.5838 (3)	−0.5168 (3)	0.63321 (14)	0.0429 (6)
H13	0.6818	−0.5221	0.6481	0.051*

	U11	U22	U33	U12	U13	U23
O10	0.0292 (9)	0.0298 (8)	0.0334 (8)	0.0001 (6)	−0.0032 (6)	−0.0002 (6)
O21	0.0357 (9)	0.0365 (9)	0.0391 (9)	−0.0021 (7)	0.0032 (7)	0.0071 (7)
O1	0.0433 (9)	0.0239 (8)	0.0228 (7)	0.0043 (7)	0.0059 (6)	−0.0005 (6)
O14	0.0641 (12)	0.0332 (10)	0.0302 (8)	0.0141 (8)	0.0060 (7)	−0.0034 (7)
C16	0.0351 (13)	0.0383 (13)	0.0263 (11)	0.0022 (10)	0.0027 (9)	0.0027 (9)
C5	0.0274 (11)	0.0224 (11)	0.0275 (10)	0.0011 (8)	0.0006 (8)	0.0005 (8)
C9	0.0311 (12)	0.0276 (11)	0.0262 (10)	0.0018 (9)	0.0017 (8)	0.0045 (9)
C11	0.0361 (13)	0.0273 (11)	0.0367 (12)	0.0042 (10)	0.0008 (9)	0.0006 (9)
C8	0.0245 (11)	0.0258 (11)	0.0296 (10)	0.0006 (9)	−0.0016 (8)	0.0017 (8)
C2	0.0389 (13)	0.0326 (12)	0.0243 (10)	0.0026 (10)	0.0024 (9)	−0.0039 (9)
C12	0.0388 (15)	0.0298 (12)	0.0296 (11)	0.0069 (10)	0.0045 (9)	−0.0020 (9)
C4	0.0270 (11)	0.0273 (11)	0.0238 (10)	−0.0027 (9)	−0.0016 (8)	0.0008 (8)
C6	0.0225 (10)	0.0273 (11)	0.0235 (10)	−0.0015 (8)	0.0013 (8)	−0.0014 (8)
C17	0.0456 (15)	0.0438 (14)	0.0328 (12)	0.0013 (12)	−0.0017 (10)	0.0099 (10)
C7	0.0296 (12)	0.0271 (11)	0.0278 (10)	0.0013 (9)	0.0025 (8)	−0.0019 (8)
C15	0.0279 (12)	0.0284 (11)	0.0227 (10)	−0.0049 (9)	−0.0007 (8)	−0.0016 (8)
C20	0.0339 (13)	0.0368 (13)	0.0269 (11)	−0.0016 (10)	0.0040 (9)	−0.0015 (9)
C3	0.0362 (13)	0.0343 (12)	0.0219 (10)	0.0019 (10)	0.0040 (9)	0.0011 (8)
C19	0.0399 (14)	0.0498 (15)	0.0281 (11)	−0.0069 (11)	0.0096 (9)	−0.0014 (10)
C18	0.0477 (15)	0.0494 (15)	0.0265 (11)	−0.0089 (12)	0.0006 (10)	0.0096 (10)
C13	0.0374 (15)	0.0505 (16)	0.0407 (13)	0.0106 (12)	−0.0011 (11)	−0.0062 (11)

O10—C8	1.436 (2)	C11—H11B	0.9700
O10—H10	0.8200	C8—C7	1.533 (3)
O21—H21A	1.0020	C2—C3	1.437 (3)
O21—H21B	1.0021	C12—C13	1.179 (3)
O1—C2	1.384 (2)	C4—C3	1.341 (3)
O1—C5	1.397 (2)	C6—C15	1.473 (3)
O14—C2	1.215 (3)	C6—C7	1.521 (3)
C16—C17	1.386 (3)	C17—C18	1.383 (4)
C16—C15	1.405 (3)	C17—H17	0.9300
C16—H16	0.9300	C7—H7A	0.9700
C5—C6	1.344 (3)	C7—H7B	0.9700
C5—C4	1.444 (3)	C15—C20	1.403 (3)
C9—C4	1.492 (3)	C20—C19	1.387 (3)
C9—C8	1.528 (3)	C20—H20	0.9300
C9—H9A	0.9700	C3—H3	0.9300
C9—H9B	0.9700	C19—C18	1.381 (3)
C11—C12	1.463 (3)	C19—H19	0.9300
C11—C8	1.538 (3)	C18—H18	0.9300
C11—H11A	0.9700	C13—H13	0.9300
C8—O10—H10	109.5	C3—C4—C5	107.93 (18)
H21A—O21—H21B	107.9	C3—C4—C9	132.25 (18)
C2—O1—C5	106.88 (15)	C5—C4—C9	119.83 (17)
C17—C16—C15	120.6 (2)	C5—C6—C15	126.24 (19)
C17—C16—H16	119.7	C5—C6—C7	114.96 (17)
C15—C16—H16	119.7	C15—C6—C7	118.79 (16)
C6—C5—O1	125.43 (18)	C18—C17—C16	120.4 (2)
C6—C5—C4	126.35 (19)	C18—C17—H17	119.8
O1—C5—C4	108.21 (16)	C16—C17—H17	119.8
C4—C9—C8	109.49 (16)	C6—C7—C8	113.49 (16)
C4—C9—H9A	109.8	C6—C7—H7A	108.9
C8—C9—H9A	109.8	C8—C7—H7A	108.9
C4—C9—H9B	109.8	C6—C7—H7B	108.9
C8—C9—H9B	109.8	C8—C7—H7B	108.9
H9A—C9—H9B	108.2	H7A—C7—H7B	107.7
C12—C11—C8	114.41 (18)	C20—C15—C16	117.96 (19)
C12—C11—H11A	108.7	C20—C15—C6	119.86 (19)
C8—C11—H11A	108.7	C16—C15—C6	122.15 (19)
C12—C11—H11B	108.7	C19—C20—C15	120.8 (2)
C8—C11—H11B	108.7	C19—C20—H20	119.6
H11A—C11—H11B	107.6	C15—C20—H20	119.6
O10—C8—C9	106.40 (16)	C4—C3—C2	108.20 (18)
O10—C8—C7	108.67 (15)	C4—C3—H3	125.9
C9—C8—C7	110.64 (17)	C2—C3—H3	125.9
O10—C8—C11	107.82 (16)	C18—C19—C20	120.3 (2)
C9—C8—C11	111.90 (16)	C18—C19—H19	119.9
C7—C8—C11	111.21 (17)	C20—C19—H19	119.9
O14—C2—O1	119.52 (19)	C19—C18—C17	119.9 (2)
O14—C2—C3	131.7 (2)	C19—C18—H18	120.0
O1—C2—C3	108.78 (17)	C17—C18—H18	120.0
C13—C12—C11	178.7 (2)	C12—C13—H13	180.0
C2—O1—C5—C6	179.1 (2)	C5—C6—C7—C8	30.3 (3)
C2—O1—C5—C4	−0.7 (2)	C15—C6—C7—C8	−150.71 (18)
C4—C9—C8—O10	−66.2 (2)	O10—C8—C7—C6	60.3 (2)
C4—C9—C8—C7	51.7 (2)	C9—C8—C7—C6	−56.2 (2)
C4—C9—C8—C11	176.32 (17)	C11—C8—C7—C6	178.83 (16)
C12—C11—C8—O10	178.87 (16)	C17—C16—C15—C20	−0.2 (3)
C12—C11—C8—C9	−64.5 (2)	C17—C16—C15—C6	−178.1 (2)
C12—C11—C8—C7	59.8 (2)	C5—C6—C15—C20	156.6 (2)
C5—O1—C2—O14	−179.3 (2)	C7—C6—C15—C20	−22.3 (3)
C5—O1—C2—C3	0.9 (2)	C5—C6—C15—C16	−25.5 (3)
C6—C5—C4—C3	−179.6 (2)	C7—C6—C15—C16	155.6 (2)
O1—C5—C4—C3	0.2 (2)	C16—C15—C20—C19	0.7 (3)
C6—C5—C4—C9	0.0 (3)	C6—C15—C20—C19	178.67 (19)
O1—C5—C4—C9	179.82 (17)	C5—C4—C3—C2	0.3 (2)
C8—C9—C4—C3	154.0 (2)	C9—C4—C3—C2	−179.2 (2)
C8—C9—C4—C5	−25.5 (3)	O14—C2—C3—C4	179.5 (2)
O1—C5—C6—C15	−0.8 (3)	O1—C2—C3—C4	−0.8 (2)
C4—C5—C6—C15	179.0 (2)	C15—C20—C19—C18	−0.6 (3)
O1—C5—C6—C7	178.16 (18)	C20—C19—C18—C17	−0.1 (4)
C4—C5—C6—C7	−2.1 (3)	C16—C17—C18—C19	0.7 (4)
C15—C16—C17—C18	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O21	0.82	1.94	2.735 (2)	163
O21—H21A···O10i	1.00	1.74	2.728 (2)	169
O21—H21B···O14ii	1.00	1.75	2.754 (2)	176
C13—H13···O21iii	0.93	2.47	3.236 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10⋯O21	0.82	1.94	2.735 (2)	163
O21—H21A⋯O10i	1.00	1.74	2.728 (2)	169
O21—H21B⋯O14ii	1.00	1.75	2.754 (2)	176
C13—H13⋯O21iii	0.93	2.47	3.236 (3)	139

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