The chalcone derivative (E)-1-(4-fluoro-phen-yl)-3-(4-hy-droxy-3-meth-oxy-phen-yl)prop-2-en-1-one monohydrate.

The title compound, C16H13FO3·H2O, has a cis disposition of the carbonyl and olefin bonds about the enone single bond. The arene rings are inclined to one another by 10.05 (6) Å. In the crystal, mol-ecules are linked via O-H⋯O hydrogen bonds involving the water mol-ecules, forming loops which are, in turn, linked via O-H.·O and C-H⋯F hydrogen bonds, forming sheets lying parallel to (103). These networks are linked via π-π inter-actions [centroid-centroid distance = 3.641 (1) Å] involving inversion-related 4-fluoro-phenyl and 4-hy-droxy-3-meth-oxy-phenyl rings.

Related literature

For background information on the biological activity of chalcones, see: Anto et al. (1995 ▶); Calliste et al. (2001 ▶); Nowakowska (2007 ▶); Kontogiorgis et al. (2008 ▶); Ducki (2009 ▶); Batovska & Todorova (2010 ▶); Batovska & Parushev (2010 ▶); Gupta et al. (2010 ▶); Varinska et al. (2010 ▶); Katsori & Hadjipavlou-Litina (2011 ▶); Orlikova, et al. (2011 ▶); Yadav et al. (2011 ▶); Kathiravan et al. (2012 ▶); Sahu et al. (2012 ▶). For related chalcone structures, see: Rabinovich (1970 ▶); Ohkura et al. (1973 ▶); Hunter & Sanders (1990 ▶); Arai et al. (1994 ▶); Wu et al. (2006 ▶); Teh et al. (2006 ▶); Yathirajan et al. (2006 ▶, 2007 ▶); Butcher et al. (2007 ▶); Hayashi et al. (2009 ▶).

Experimental

Crystal data

C16H13FO3·H2O

M = 290.29

Monoclinic,

a = 9.787 (2) Å

b = 10.993 (3) Å

c = 12.781 (3) Å

β = 95.722 (4)°

V = 1368.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.34 × 0.27 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2009 ▶) T min = 0.845, T max = 0.978

11909 measured reflections

3203 independent reflections

2855 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.02

3203 reflections

250 parameters

All H-atom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681300696X/pk2468sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300696X/pk2468Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300696X/pk2468Isup3.cml

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

C16H13FO3·H2O	F(000) = 608
Mr = 290.29	Dx = 1.409 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7532 reflections
a = 9.787 (2) Å	θ = 28.3–2.5°
b = 10.993 (3) Å	µ = 0.11 mm−1
c = 12.781 (3) Å	T = 100 K
β = 95.722 (4)°	Needle, pale yellow
V = 1368.2 (5) Å3	0.34 × 0.27 × 0.21 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3203 independent reflections
Radiation source: fine-focus sealed tube	2855 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2009)	h = −13→12
Tmin = 0.845, Tmax = 0.978	k = −13→14
11909 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	All H-atom parameters refined
S = 1.02	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.5324P] where P = (Fo2 + 2Fc2)/3
3203 reflections	(Δ/σ)max = 0.001
250 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The diffraction data were obtained from 3 sets of 606 frames, each of width 0.3 ° in ω, collected at φ = 0.00, 120.00 and 240.00 °. The scan time was 30 sec/frame.

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 > 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
F1	1.90355 (8)	−0.41277 (7)	0.21518 (6)	0.0284 (2)
O1	1.40402 (9)	−0.31928 (8)	0.47673 (7)	0.0243 (2)
O2	1.03808 (9)	0.36973 (8)	0.45389 (7)	0.0216 (2)
H2	0.977 (2)	0.3730 (17)	0.5032 (16)	0.043 (5)*
O3	1.23977 (10)	0.34671 (8)	0.33849 (7)	0.0237 (2)
O4	1.14188 (10)	−0.39678 (10)	0.40629 (8)	0.0266 (2)
H4A	1.227 (2)	−0.378 (2)	0.4266 (16)	0.052 (6)*
H4B	1.141 (2)	−0.472 (2)	0.3984 (17)	0.063 (7)*
C1	1.45724 (12)	−0.24717 (11)	0.41849 (9)	0.0184 (3)
C2	1.57311 (12)	−0.28995 (11)	0.36004 (9)	0.0178 (2)
C3	1.61894 (13)	−0.22551 (11)	0.27605 (10)	0.0210 (3)
H3	1.5730 (17)	−0.1494 (16)	0.2507 (13)	0.031 (4)*
C4	1.72921 (14)	−0.26744 (12)	0.22595 (10)	0.0233 (3)
H4	1.7621 (17)	−0.2243 (16)	0.1683 (13)	0.030 (4)*
C5	1.79286 (13)	−0.37355 (12)	0.26222 (10)	0.0215 (3)
C6	1.75010 (13)	−0.44096 (11)	0.34390 (10)	0.0211 (3)
H6	1.7980 (16)	−0.5140 (16)	0.3672 (12)	0.029 (4)*
C7	1.63853 (13)	−0.39926 (11)	0.39241 (10)	0.0201 (3)
H7	1.6074 (16)	−0.4430 (14)	0.4491 (13)	0.024 (4)*
C8	1.41072 (13)	−0.12016 (11)	0.40715 (10)	0.0195 (3)
H8	1.4531 (16)	−0.0693 (15)	0.3609 (13)	0.027 (4)*
C9	1.31350 (12)	−0.07855 (11)	0.46511 (10)	0.0189 (3)
H9	1.2769 (16)	−0.1366 (15)	0.5109 (12)	0.024 (4)*
C10	1.25059 (12)	0.04162 (11)	0.46436 (9)	0.0182 (2)
C11	1.14937 (13)	0.06159 (11)	0.53213 (10)	0.0196 (3)
H11	1.1290 (16)	−0.0018 (16)	0.5787 (13)	0.028 (4)*
C12	1.07706 (12)	0.17051 (11)	0.53043 (10)	0.0199 (3)
H12	1.0059 (16)	0.1842 (14)	0.5779 (12)	0.024 (4)*
C13	1.10616 (12)	0.26192 (11)	0.46193 (9)	0.0182 (3)
C14	1.21398 (12)	0.24626 (11)	0.39687 (9)	0.0187 (3)
C15	1.28376 (12)	0.13679 (11)	0.39695 (10)	0.0189 (3)
H15	1.3551 (16)	0.1271 (15)	0.3518 (13)	0.026 (4)*
C16	1.36498 (14)	0.34589 (13)	0.28868 (11)	0.0250 (3)
H16A	1.4443 (17)	0.3331 (15)	0.3422 (13)	0.028 (4)*
H16C	1.3620 (16)	0.2806 (14)	0.2335 (12)	0.023 (4)*
H16B	1.3695 (17)	0.4287 (15)	0.2550 (13)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0297 (4)	0.0264 (4)	0.0307 (4)	0.0078 (3)	0.0101 (3)	−0.0034 (3)
O1	0.0235 (5)	0.0194 (4)	0.0306 (5)	−0.0001 (4)	0.0062 (4)	0.0052 (4)
O2	0.0219 (4)	0.0178 (4)	0.0252 (5)	0.0039 (3)	0.0035 (4)	−0.0002 (3)
O3	0.0272 (5)	0.0195 (5)	0.0254 (5)	0.0023 (4)	0.0075 (4)	0.0047 (3)
O4	0.0229 (5)	0.0207 (5)	0.0369 (6)	0.0017 (4)	0.0063 (4)	0.0015 (4)
C1	0.0169 (5)	0.0181 (6)	0.0195 (6)	−0.0012 (4)	−0.0010 (4)	0.0003 (4)
C2	0.0186 (6)	0.0152 (5)	0.0191 (6)	−0.0001 (4)	−0.0006 (4)	−0.0014 (4)
C3	0.0260 (6)	0.0160 (6)	0.0209 (6)	0.0026 (5)	0.0017 (5)	−0.0001 (4)
C4	0.0307 (7)	0.0188 (6)	0.0213 (6)	0.0017 (5)	0.0070 (5)	0.0005 (5)
C5	0.0228 (6)	0.0202 (6)	0.0218 (6)	0.0028 (5)	0.0031 (5)	−0.0064 (5)
C6	0.0245 (6)	0.0155 (6)	0.0224 (6)	0.0043 (5)	−0.0018 (5)	−0.0021 (4)
C7	0.0243 (6)	0.0158 (6)	0.0199 (6)	−0.0001 (5)	0.0014 (5)	−0.0001 (5)
C8	0.0194 (6)	0.0170 (6)	0.0219 (6)	−0.0007 (5)	0.0013 (5)	0.0014 (5)
C9	0.0189 (6)	0.0175 (6)	0.0198 (6)	−0.0016 (4)	−0.0004 (5)	0.0011 (4)
C10	0.0178 (5)	0.0180 (6)	0.0183 (6)	−0.0003 (4)	−0.0005 (4)	−0.0016 (4)
C11	0.0201 (6)	0.0183 (6)	0.0206 (6)	−0.0025 (5)	0.0021 (5)	0.0007 (5)
C12	0.0176 (6)	0.0206 (6)	0.0218 (6)	−0.0008 (4)	0.0031 (5)	−0.0022 (5)
C13	0.0172 (5)	0.0167 (6)	0.0201 (6)	0.0009 (4)	−0.0011 (4)	−0.0031 (4)
C14	0.0199 (6)	0.0179 (6)	0.0179 (6)	−0.0013 (4)	0.0003 (5)	0.0004 (4)
C15	0.0185 (6)	0.0201 (6)	0.0183 (6)	0.0000 (4)	0.0024 (4)	−0.0008 (4)
C16	0.0262 (7)	0.0247 (7)	0.0247 (6)	−0.0011 (5)	0.0064 (5)	0.0046 (5)

F1—C5	1.3604 (14)	C6—H6	0.962 (17)
O1—C1	1.2374 (15)	C7—H7	0.945 (16)
O2—C13	1.3585 (15)	C8—C9	1.3430 (18)
O2—H2	0.91 (2)	C8—H8	0.939 (17)
O3—C14	1.3702 (15)	C9—C10	1.4572 (17)
O3—C16	1.4361 (16)	C9—H9	0.960 (16)
O4—H4A	0.88 (2)	C10—C11	1.3968 (17)
O4—H4B	0.83 (3)	C10—C15	1.4135 (17)
C1—C8	1.4712 (17)	C11—C12	1.3899 (18)
C1—C2	1.4947 (17)	C11—H11	0.950 (17)
C2—C3	1.3969 (18)	C12—C13	1.3811 (18)
C2—C7	1.4043 (17)	C12—H12	0.980 (16)
C3—C4	1.3874 (18)	C13—C14	1.4175 (17)
C3—H3	0.989 (17)	C14—C15	1.3837 (17)
C4—C5	1.3807 (18)	C15—H15	0.955 (16)
C4—H4	0.959 (17)	C16—H16A	0.992 (17)
C5—C6	1.3788 (19)	C16—H16C	1.005 (16)
C6—C7	1.3863 (18)	C16—H16B	1.009 (17)
C13—O2—H2	109.5 (12)	C8—C9—C10	128.85 (12)
C14—O3—C16	116.62 (10)	C8—C9—H9	116.0 (9)
H4A—O4—H4B	106 (2)	C10—C9—H9	115.1 (9)
O1—C1—C8	121.50 (11)	C11—C10—C15	118.81 (11)
O1—C1—C2	119.00 (11)	C11—C10—C9	117.62 (11)
C8—C1—C2	119.48 (11)	C15—C10—C9	123.54 (11)
C3—C2—C7	119.24 (11)	C12—C11—C10	121.14 (12)
C3—C2—C1	122.83 (11)	C12—C11—H11	120.2 (10)
C7—C2—C1	117.93 (11)	C10—C11—H11	118.7 (10)
C4—C3—C2	120.69 (12)	C13—C12—C11	120.00 (11)
C4—C3—H3	118.6 (10)	C13—C12—H12	119.0 (9)
C2—C3—H3	120.7 (10)	C11—C12—H12	121.0 (9)
C5—C4—C3	118.12 (12)	O2—C13—C12	123.52 (11)
C5—C4—H4	120.1 (10)	O2—C13—C14	116.73 (11)
C3—C4—H4	121.8 (10)	C12—C13—C14	119.74 (11)
F1—C5—C6	118.65 (11)	O3—C14—C15	125.71 (11)
F1—C5—C4	118.15 (12)	O3—C14—C13	114.20 (10)
C6—C5—C4	123.19 (12)	C15—C14—C13	120.09 (11)
C5—C6—C7	118.23 (12)	C14—C15—C10	120.06 (11)
C5—C6—H6	120.5 (9)	C14—C15—H15	119.1 (10)
C7—C6—H6	121.2 (9)	C10—C15—H15	120.8 (10)
C6—C7—C2	120.49 (12)	O3—C16—H16A	109.8 (9)
C6—C7—H7	120.2 (10)	O3—C16—H16C	110.4 (9)
C2—C7—H7	119.3 (9)	H16A—C16—H16C	110.4 (13)
C9—C8—C1	119.88 (11)	O3—C16—H16B	105.0 (10)
C9—C8—H8	121.7 (10)	H16A—C16—H16B	110.9 (14)
C1—C8—H8	118.4 (10)	H16C—C16—H16B	110.1 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4i	0.91 (2)	1.74 (2)	2.6479 (14)	173.5 (18)
O4—H4A···O1	0.88 (2)	1.90 (2)	2.7672 (15)	173 (2)
O4—H4B···O2ii	0.83 (3)	2.17 (3)	2.8485 (15)	139 (2)
O4—H4B···O3ii	0.83 (3)	2.38 (3)	3.1283 (15)	151 (2)
C8—H8···F1iii	0.94 (2)	2.48 (2)	3.3931 (17)	164 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4i	0.91 (2)	1.74 (2)	2.6479 (14)	173.5 (18)
O4—H4A⋯O1	0.88 (2)	1.90 (2)	2.7672 (15)	173 (2)
O4—H4B⋯O2ii	0.83 (3)	2.17 (3)	2.8485 (15)	139 (2)
O4—H4B⋯O3ii	0.83 (3)	2.38 (3)	3.1283 (15)	151 (2)
C8—H8⋯F1iii	0.94 (2)	2.48 (2)	3.3931 (17)	164 (1)

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