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In the title mol­ecule, C15H11FO2, the 3-hydroxy­phenyl and 4-fluoro­phenyl groups are coplanar with each other and also with the plane of the prop-2-en-1-one linkage. Crystal packing is stabilized by inter­molecular O—H...O hydrogen bonding between the hydroxyl H atom and the prop-2-en-1-one O atom, which links the mol­ecules into a chain along the [010] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034964/ci2418sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034964/ci2418Isup2.hkl
Contains datablock I

CCDC reference: 657825

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.046
  • wR factor = 0.145
  • Data-to-parameter ratio = 24.6

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.643 1.000 Tmin(prime) and Tmax expected: 0.942 0.970 RR(prime) = 0.662 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.66
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Chalcones are known for their anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities. Among several organic compounds reported for non-linear optical (NLO) properties, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. We have synthesized a new chalcone, the title compound. In view of the importance of the title compound, its crystal structure is reported here.

The 3-hydroxyphenyl and 4-fluorophenyl groups of the title molecule (Fig. 1) are coplanar [dihedral angle = 3.11 (8)°] with each other and also with the propyl-2-ketone group, forming torsion angles C8—C9—C10—C11 and C8—C7—C1—C6 of 4.9 (2)° and -1.75 (18)°, respectively.

Intermolecular O—H···O hydrogen bonding interactions (Table 1) involving the hydroxyl group and the carbonyl O atom link the molecules into a chain along the [0 1 0] direction (Fig. 2).

Related literature top

For related structures, see: Butcher et al. (2006); Yathirajan et al. (2006, 2007); Fischer et al. (2007); Harrison et al. (2006). For related literature, see: Carlo et al. (1999); Fichou et al. (1988); Goto et al. (1991); Uchida et al. (1998); Zhao et al. (2000); Sarojini et al. (2006).

Experimental top

To a mixture of 1-(3-hydroxyphenyl)ethanone (1.36 g, 0.01 mol) and 4-fluoroacetophenone (1.38 g, 0.01 mol) in ethanol (20 ml), a solution of potassium hydroxide (5%, 5 ml) was added slowly with stirring. The mixture was stirred at room temperature for 6 h. The solid that precipitated was filtered off and washed with cold ethanol, dried and recrystallized from ethanol. X-ray quality crystals were obtained from ethyl acetate by slow evaporation (yield: 80%; m.p. 408–09 K). Analysis found: C 74.30, H 4.51%; C15H11ClO2 requires: C 74.37, H 4.58%.

Refinement top

All H atoms, except H1, were found in a difference map. But all H atoms were refined using a riding model with O—H = 0.83 Å and C—H = 0.94 Å, and with Uiso(H) = 1.19–1.20 Ueq(C,O). Owing to the poor diffraction quality of the crystal, the ratio of observed to unique reflections is low (47%).

Structure description top

Chalcones are known for their anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities. Among several organic compounds reported for non-linear optical (NLO) properties, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. We have synthesized a new chalcone, the title compound. In view of the importance of the title compound, its crystal structure is reported here.

The 3-hydroxyphenyl and 4-fluorophenyl groups of the title molecule (Fig. 1) are coplanar [dihedral angle = 3.11 (8)°] with each other and also with the propyl-2-ketone group, forming torsion angles C8—C9—C10—C11 and C8—C7—C1—C6 of 4.9 (2)° and -1.75 (18)°, respectively.

Intermolecular O—H···O hydrogen bonding interactions (Table 1) involving the hydroxyl group and the carbonyl O atom link the molecules into a chain along the [0 1 0] direction (Fig. 2).

For related structures, see: Butcher et al. (2006); Yathirajan et al. (2006, 2007); Fischer et al. (2007); Harrison et al. (2006). For related literature, see: Carlo et al. (1999); Fichou et al. (1988); Goto et al. (1991); Uchida et al. (1998); Zhao et al. (2000); Sarojini et al. (2006).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing atom labelling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed down the a axis. Dashed lines indicate O—H···O hydrogen bonds.
(2E)-3-(4-Fluorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one top
Crystal data top
C15H11FO2F(000) = 504
Mr = 242.24Dx = 1.342 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5107 reflections
a = 7.4149 (4) Åθ = 4.8–32.5°
b = 11.3162 (6) ŵ = 0.10 mm1
c = 14.7472 (8) ÅT = 203 K
β = 104.311 (6)°Prism, colourless
V = 1199.01 (11) Å30.59 × 0.47 × 0.31 mm
Z = 4
Data collection top
Oxford Diffraction Gemini R
diffractometer
4038 independent reflections
Radiation source: fine-focus sealed tube1916 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
Detector resolution: 10.5081 pixels mm-1θmax = 32.5°, θmin = 4.8°
φ and ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1617
Tmin = 0.643, Tmax = 1.000l = 2122
16754 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0687P)2]
where P = (Fo2 + 2Fc2)/3
4038 reflections(Δ/σ)max = 0.001
164 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C15H11FO2V = 1199.01 (11) Å3
Mr = 242.24Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.4149 (4) ŵ = 0.10 mm1
b = 11.3162 (6) ÅT = 203 K
c = 14.7472 (8) Å0.59 × 0.47 × 0.31 mm
β = 104.311 (6)°
Data collection top
Oxford Diffraction Gemini R
diffractometer
4038 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
1916 reflections with I > 2σ(I)
Tmin = 0.643, Tmax = 1.000Rint = 0.042
16754 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.06Δρmax = 0.25 e Å3
4038 reflectionsΔρmin = 0.17 e Å3
164 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F0.53494 (15)0.34667 (10)0.46126 (6)0.0827 (4)
O10.71674 (13)0.81902 (9)0.33109 (6)0.0491 (3)
H10.67310.87860.35070.059*
O20.83919 (12)0.53556 (8)0.10376 (6)0.0449 (3)
C10.65119 (16)0.70409 (10)0.09520 (8)0.0318 (3)
C20.71346 (16)0.71937 (11)0.19185 (8)0.0339 (3)
H2A0.79990.66580.22700.041*
C30.65035 (17)0.81164 (12)0.23650 (8)0.0360 (3)
C40.52401 (19)0.89189 (12)0.18486 (9)0.0436 (3)
H4A0.48120.95550.21480.052*
C50.4616 (2)0.87745 (13)0.08907 (10)0.0488 (4)
H5A0.37590.93170.05430.059*
C60.52293 (19)0.78494 (12)0.04362 (9)0.0426 (3)
H6A0.47900.77620.02150.051*
C70.72278 (15)0.60043 (10)0.05300 (8)0.0321 (3)
C80.65602 (16)0.57558 (11)0.04758 (8)0.0327 (3)
H8A0.56000.62200.08410.039*
C90.72904 (16)0.48853 (11)0.08792 (9)0.0347 (3)
H9A0.82440.44450.04850.042*
C100.67813 (16)0.45384 (11)0.18606 (9)0.0344 (3)
C110.54868 (19)0.51720 (12)0.25370 (9)0.0427 (3)
H11A0.49330.58520.23580.051*
C120.5007 (2)0.48226 (14)0.34577 (10)0.0523 (4)
H12A0.41330.52520.39080.063*
C130.5838 (2)0.38287 (15)0.37027 (10)0.0522 (4)
C140.7107 (2)0.31840 (14)0.30732 (11)0.0514 (4)
H14A0.76540.25080.32630.062*
C150.75793 (18)0.35409 (12)0.21479 (10)0.0418 (3)
H15A0.84540.31010.17060.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F0.1133 (9)0.0953 (8)0.0383 (6)0.0028 (7)0.0166 (5)0.0175 (5)
O10.0562 (6)0.0548 (6)0.0317 (5)0.0022 (5)0.0020 (4)0.0099 (4)
O20.0462 (5)0.0447 (5)0.0384 (5)0.0093 (4)0.0005 (4)0.0028 (4)
C10.0304 (6)0.0350 (6)0.0298 (6)0.0055 (5)0.0069 (5)0.0015 (5)
C20.0295 (6)0.0384 (7)0.0308 (6)0.0058 (5)0.0020 (5)0.0010 (5)
C30.0350 (7)0.0418 (7)0.0300 (7)0.0106 (5)0.0057 (5)0.0054 (5)
C40.0456 (8)0.0418 (8)0.0424 (8)0.0012 (6)0.0093 (6)0.0070 (6)
C50.0557 (9)0.0475 (8)0.0388 (8)0.0148 (7)0.0030 (6)0.0024 (6)
C60.0470 (8)0.0464 (8)0.0316 (7)0.0058 (6)0.0046 (6)0.0023 (6)
C70.0288 (6)0.0336 (6)0.0335 (6)0.0046 (5)0.0067 (5)0.0035 (5)
C80.0306 (6)0.0360 (7)0.0311 (6)0.0016 (5)0.0066 (5)0.0018 (5)
C90.0304 (6)0.0378 (7)0.0354 (7)0.0016 (5)0.0073 (5)0.0030 (5)
C100.0285 (6)0.0377 (7)0.0382 (7)0.0057 (5)0.0104 (5)0.0024 (5)
C110.0442 (7)0.0459 (8)0.0382 (8)0.0042 (6)0.0103 (6)0.0012 (6)
C120.0578 (9)0.0619 (10)0.0345 (8)0.0037 (8)0.0062 (7)0.0031 (7)
C130.0629 (10)0.0619 (10)0.0328 (8)0.0047 (8)0.0140 (7)0.0086 (7)
C140.0573 (9)0.0512 (9)0.0497 (9)0.0007 (7)0.0209 (7)0.0149 (7)
C150.0388 (7)0.0414 (8)0.0455 (8)0.0003 (6)0.0107 (6)0.0030 (6)
Geometric parameters (Å, º) top
F—C131.3635 (16)C7—C81.4700 (17)
O1—C31.3622 (15)C8—C91.3330 (17)
O1—H10.83C8—H8A0.94
O2—C71.2348 (14)C9—C101.4564 (17)
C1—C21.3962 (16)C9—H9A0.94
C1—C61.4009 (17)C10—C151.3884 (18)
C1—C71.4861 (17)C10—C111.3989 (18)
C2—C31.3766 (18)C11—C121.3739 (19)
C2—H2A0.94C11—H11A0.94
C3—C41.3890 (18)C12—C131.373 (2)
C4—C51.3832 (18)C12—H12A0.94
C4—H4A0.94C13—C141.359 (2)
C5—C61.379 (2)C14—C151.3825 (19)
C5—H5A0.94C14—H14A0.94
C6—H6A0.94C15—H15A0.94
C3—O1—H1109.5C9—C8—H8A119.4
C2—C1—C6118.83 (11)C7—C8—H8A119.4
C2—C1—C7117.59 (11)C8—C9—C10127.49 (12)
C6—C1—C7123.58 (11)C8—C9—H9A116.3
C3—C2—C1121.10 (11)C10—C9—H9A116.3
C3—C2—H2A119.4C15—C10—C11117.91 (12)
C1—C2—H2A119.4C15—C10—C9119.80 (12)
O1—C3—C2117.18 (11)C11—C10—C9122.28 (12)
O1—C3—C4123.05 (12)C12—C11—C10121.45 (13)
C2—C3—C4119.77 (12)C12—C11—H11A119.3
C5—C4—C3119.51 (13)C10—C11—H11A119.3
C5—C4—H4A120.2C13—C12—C11118.18 (14)
C3—C4—H4A120.2C13—C12—H12A120.9
C6—C5—C4121.25 (13)C11—C12—H12A120.9
C6—C5—H5A119.4C14—C13—F118.79 (14)
C4—C5—H5A119.4C14—C13—C12122.68 (13)
C5—C6—C1119.53 (12)F—C13—C12118.53 (14)
C5—C6—H6A120.2C13—C14—C15118.74 (14)
C1—C6—H6A120.2C13—C14—H14A120.6
O2—C7—C8120.57 (11)C15—C14—H14A120.6
O2—C7—C1118.94 (11)C14—C15—C10121.04 (13)
C8—C7—C1120.49 (10)C14—C15—H15A119.5
C9—C8—C7121.27 (11)C10—C15—H15A119.5
C6—C1—C2—C30.27 (18)C1—C7—C8—C9174.75 (11)
C7—C1—C2—C3178.49 (11)C7—C8—C9—C10179.81 (10)
C1—C2—C3—O1179.23 (10)C8—C9—C10—C15174.46 (12)
C1—C2—C3—C40.65 (19)C8—C9—C10—C114.9 (2)
O1—C3—C4—C5179.26 (12)C15—C10—C11—C120.2 (2)
C2—C3—C4—C50.6 (2)C9—C10—C11—C12179.18 (12)
C3—C4—C5—C60.2 (2)C10—C11—C12—C130.2 (2)
C4—C5—C6—C10.2 (2)C11—C12—C13—C140.0 (2)
C2—C1—C6—C50.15 (19)C11—C12—C13—F179.08 (13)
C7—C1—C6—C5178.82 (13)F—C13—C14—C15178.96 (12)
C2—C1—C7—O23.07 (16)C12—C13—C14—C150.1 (2)
C6—C1—C7—O2178.24 (11)C13—C14—C15—C100.1 (2)
C2—C1—C7—C8176.94 (10)C11—C10—C15—C140.10 (19)
C6—C1—C7—C81.75 (18)C9—C10—C15—C14179.32 (12)
O2—C7—C8—C95.25 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.831.912.7013 (13)159
Symmetry code: (i) x+3/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H11FO2
Mr242.24
Crystal system, space groupMonoclinic, P21/n
Temperature (K)203
a, b, c (Å)7.4149 (4), 11.3162 (6), 14.7472 (8)
β (°) 104.311 (6)
V3)1199.01 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.59 × 0.47 × 0.31
Data collection
DiffractometerOxford Diffraction Gemini R
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.643, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
16754, 4038, 1916
Rint0.042
(sin θ/λ)max1)0.755
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.145, 1.06
No. of reflections4038
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.831.912.7013 (13)159
Symmetry code: (i) x+3/2, y+1/2, z+1/2.
 

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