(E)-3-(4-Fluoro­phen­yl)-1-(4-methyl­phen­yl)­prop-2-en-1-one

In the title mol­ecule, C₁₆H₁₃FO, the planar 4-fluoro­phenyl and 4-methyl­phenyl groups are twisted from the prop-2-en-1-one group by 23.6 (6) and 18.9 (2)°, respectively, and by 26.1 (6)° from each other. The crystal packing is stabilized by inter­molecular C—H...O hydrogen bonding between a 4-methyl­phenyl hydrogen and the prop-2-en-1-one group, which links the mol­ecules into a chain along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 203 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.137
• Data-to-parameter ratio = 24.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.736     1.000
            Tmin(prime) and Tmax expected:      0.950     0.972
            RR(prime) =      0.754
            Please check that your absorption correction is appropriate.
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      15.99
            Cell volume su given      =      13.00
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.75
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       6.78 su

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.972
            Tmax scaled      0.972 Tmin scaled      0.716

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

---

S1. Comment

Chalcones are one of the major classes of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff and have recently been subjects of great interest for their interesting pharmacological activities (Di Carlo et al., 1999). A vast number of naturally occurring chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using these compounds or chalcone rich plant extracts as drugs or food preservatives (Dhar, 1981). Chalcones can be easily obtained from the aldol condensation of aromatic aldehydes and aromatic ketones. This class of compounds presents interesting biological properties such as cytotoxicity (Pandey et al., 2005; Bhat et al., 2005), antiherpes and antitumour activity and may be useful for the chemotherapy of leishmaniasis among others (Lawrence et al., 2001). A review on the bioactivities of chalcones is described (Dimmock et al., 1999). Chalcones and their heterocyclic analogs as potential antifungal chemotherapeutic agents (Opletalova & Sedivy, 1999) and chalcones and flavonoids as anti-tuberculosis agents have been published (Lin et al., 2002). Several organic compounds of chalcone derivatives are reported to have non-linear optics (NLO) properties because of their excellent blue light transmittance and good crystallization ability (Goto et al., 1991; Indira et al., 2002; Sarojini et al., 2006). The crystal structures of some fluorinated chalcones, viz., 1-(2,4-dichloro-5-fluorophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (Yathirajan et al., 2006), 1-(4-fluorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (Harrison et al., 2006) and 3-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one (Butcher et al., 2005) have been reported. In continuation of our work on chalcones, a new chalcone, (I), C₁₆H₁₃FO is synthesized and its crystal structure is reported.

The planar 4-fluorophenyl and 4-methylphenyl groups of the title molecule (Fig. 1) are twisted from the prop-2-en-1-one group by 23.6 (6) and 18.9 (2)°, respectively, and 26.1 (6)° from each other forming torsion angles of -12.7 (3)° [C9–C10–C11–C12] and 13.7 (2)° [C6–C1–C8–C9].

Intermolecular C—H···O hydrogen bonding interactions (Table 1) between H2A from the 4-methylphenyl group and the prop-2-en-1-one oxygen, which link the molecules into a chain along the b axis, stabilize crystal packing (Fig. 2).

Related literature

For related structure, see: Yathirajan et al. (2006); Harrison et al. (2006); Butcher et al. (2006 or???2005). For related literature, see: Goto et al. (1991); Indira et al. (2002); Lawrence et al. (2001); Pandey et al. (2005); Sarojini et al. (2006); Bhat et al. (2005); Dhar (1981); Di Carlo et al. (1999); Dimmock et al. (1999); Lin et al. (2002); Opletalova & Sedivy (1999).

S2. Experimental

4-Fluorobenzaldehyde (1.5 ml, 0.01 mol) in ethanol (50 ml) was mixed with 1-(4-methyl phenyl) ethanone (1.34 ml, 0.01 mol) and the mixture was treated with 10 ml of 10% KOH. The reaction mixture was then kept for constant stirring. The solid precipitate obtained was filtered, washed with alcohol and dried. The crystal growth was carried out in acetone by the slow evaporation technique (m.p.: 400 K). Analysis found: C 79.89, H 5.36%; C₁₆H₁₃FO requires: C 79.98, H 5.45%.

S3. Refinement

The H atoms, were refined using a riding model with C—H = 0.94–0.97 Å, and with U_iso(H) = 1.18–1.50U_eq(C).

Computing details

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

Figures

	Fig. 1. Molecular structure of the title compound, showing atom labelling and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, viewed down the a axis. Dashed lines indicate C—H···O hydrogen bonds.

(E)-3-(4-Fluorophenyl)-1-(4-methylphenyl)prop-2-en-1-one

Crystal data

C16H13FO	F(000) = 504
Mr = 240.26	Dx = 1.313 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3092 reflections
a = 11.0082 (7) Å	θ = 5.1–32.5°
b = 10.7499 (6) Å	µ = 0.09 mm^−1
c = 11.5415 (7) Å	T = 203 K
β = 117.122 (9)°	Prism, colorless
V = 1215.60 (13) Å^3	0.55 × 0.47 × 0.31 mm
Z = 4

Data collection

Oxford Diffraction Gemini R CCD diffractometer	4010 independent reflections
Radiation source: fine-focus sealed tube	1699 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 10.5081 pixels mm^-1	θmax = 32.5°, θmin = 5.1°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −13→15
Tmin = 0.737, Tmax = 1.000	l = −17→16
11487 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0694P)^2] where P = (Fo^2 + 2Fc^2)/3
4010 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	1.05207 (9)	0.89421 (9)	0.09765 (9)	0.0545 (3)
O1	0.52636 (11)	0.57091 (10)	0.35150 (10)	0.0447 (3)
C1	0.43320 (13)	0.75350 (13)	0.39312 (12)	0.0319 (3)
C2	0.38265 (14)	0.68882 (13)	0.46662 (13)	0.0346 (3)
H2A	0.4031	0.6039	0.4844	0.042*
C3	0.30284 (14)	0.74811 (15)	0.51359 (13)	0.0392 (4)
H3A	0.2703	0.7028	0.5634	0.047*
C4	0.26944 (14)	0.87354 (14)	0.48879 (13)	0.0382 (4)
C5	0.32190 (15)	0.93751 (15)	0.41701 (15)	0.0421 (4)
H5A	0.3024	1.0227	0.4003	0.050*
C6	0.40182 (15)	0.87941 (14)	0.36952 (15)	0.0393 (4)
H6A	0.4354	0.9252	0.3208	0.047*
C7	0.18030 (18)	0.93690 (17)	0.53779 (17)	0.0580 (5)
H7A	0.1745	1.0249	0.5174	0.087*
H7B	0.2191	0.9261	0.6313	0.087*
H7C	0.0897	0.9006	0.4963	0.087*
C8	0.52024 (14)	0.68530 (14)	0.34601 (13)	0.0330 (3)
C9	0.60209 (14)	0.75656 (14)	0.29695 (13)	0.0355 (3)
H9A	0.5780	0.8391	0.2689	0.043*
C10	0.70932 (14)	0.70500 (13)	0.29217 (14)	0.0356 (3)
H10A	0.7300	0.6231	0.3237	0.043*
C11	0.79915 (13)	0.75967 (13)	0.24395 (13)	0.0324 (3)
C12	0.76801 (14)	0.86948 (14)	0.17171 (13)	0.0354 (4)
H12A	0.6879	0.9130	0.1560	0.042*
C13	0.85251 (15)	0.91552 (14)	0.12290 (14)	0.0395 (4)
H13A	0.8311	0.9896	0.0744	0.047*
C14	0.96921 (14)	0.84977 (15)	0.14727 (14)	0.0380 (4)
C15	1.00536 (14)	0.74242 (15)	0.21885 (14)	0.0423 (4)
H15A	1.0866	0.7004	0.2354	0.051*
C16	0.91890 (15)	0.69798 (14)	0.26577 (14)	0.0411 (4)
H16A	0.9414	0.6237	0.3140	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0518 (6)	0.0635 (7)	0.0638 (6)	−0.0022 (4)	0.0398 (5)	0.0037 (5)
O1	0.0561 (7)	0.0299 (6)	0.0578 (7)	0.0011 (5)	0.0344 (6)	0.0029 (5)
C1	0.0322 (7)	0.0314 (8)	0.0338 (7)	−0.0024 (6)	0.0165 (6)	0.0000 (6)
C2	0.0347 (8)	0.0310 (8)	0.0382 (8)	−0.0015 (6)	0.0167 (7)	0.0033 (6)
C3	0.0392 (8)	0.0469 (10)	0.0376 (8)	−0.0066 (7)	0.0227 (7)	0.0015 (7)
C4	0.0370 (8)	0.0401 (9)	0.0403 (8)	0.0001 (7)	0.0202 (7)	−0.0032 (7)
C5	0.0484 (9)	0.0317 (8)	0.0517 (9)	0.0029 (7)	0.0277 (8)	0.0024 (7)
C6	0.0446 (8)	0.0342 (9)	0.0492 (9)	0.0008 (7)	0.0302 (8)	0.0072 (7)
C7	0.0650 (11)	0.0567 (12)	0.0707 (11)	0.0037 (9)	0.0471 (10)	−0.0056 (9)
C8	0.0311 (7)	0.0334 (9)	0.0345 (7)	0.0002 (6)	0.0149 (6)	0.0020 (6)
C9	0.0400 (8)	0.0294 (8)	0.0410 (8)	0.0013 (6)	0.0220 (7)	0.0019 (6)
C10	0.0399 (8)	0.0292 (8)	0.0415 (8)	0.0014 (6)	0.0219 (7)	0.0017 (6)
C11	0.0334 (7)	0.0308 (8)	0.0352 (7)	0.0001 (6)	0.0177 (6)	−0.0023 (6)
C12	0.0321 (7)	0.0339 (9)	0.0405 (8)	0.0029 (6)	0.0168 (7)	−0.0003 (6)
C13	0.0399 (8)	0.0372 (9)	0.0429 (8)	0.0019 (7)	0.0202 (7)	0.0049 (7)
C14	0.0361 (8)	0.0442 (10)	0.0396 (8)	−0.0048 (7)	0.0224 (7)	−0.0057 (7)
C15	0.0333 (7)	0.0501 (10)	0.0458 (9)	0.0087 (7)	0.0201 (7)	0.0011 (8)
C16	0.0439 (9)	0.0375 (9)	0.0461 (9)	0.0079 (7)	0.0241 (8)	0.0056 (7)

Geometric parameters (Å, º)

F1—C14	1.3655 (15)	C7—H7C	0.9700
O1—C8	1.2316 (16)	C8—C9	1.4779 (19)
C1—C6	1.393 (2)	C9—C10	1.3278 (19)
C1—C2	1.3940 (18)	C9—H9A	0.9400
C1—C8	1.4920 (18)	C10—C11	1.4610 (18)
C2—C3	1.3806 (19)	C10—H10A	0.9400
C2—H2A	0.9400	C11—C16	1.3921 (19)
C3—C4	1.393 (2)	C11—C12	1.395 (2)
C3—H3A	0.9400	C12—C13	1.3804 (19)
C4—C5	1.389 (2)	C12—H12A	0.9400
C4—C7	1.501 (2)	C13—C14	1.378 (2)
C5—C6	1.380 (2)	C13—H13A	0.9400
C5—H5A	0.9400	C14—C15	1.368 (2)
C6—H6A	0.9400	C15—C16	1.3775 (19)
C7—H7A	0.9700	C15—H15A	0.9400
C7—H7B	0.9700	C16—H16A	0.9400
C6—C1—C2	118.13 (12)	C9—C8—C1	119.33 (12)
C6—C1—C8	123.33 (12)	C10—C9—C8	120.56 (14)
C2—C1—C8	118.53 (13)	C10—C9—H9A	119.7
C3—C2—C1	120.72 (13)	C8—C9—H9A	119.7
C3—C2—H2A	119.6	C9—C10—C11	128.09 (14)
C1—C2—H2A	119.6	C9—C10—H10A	116.0
C2—C3—C4	121.46 (13)	C11—C10—H10A	116.0
C2—C3—H3A	119.3	C16—C11—C12	117.75 (13)
C4—C3—H3A	119.3	C16—C11—C10	119.28 (13)
C5—C4—C3	117.35 (13)	C12—C11—C10	122.92 (12)
C5—C4—C7	121.40 (14)	C13—C12—C11	121.31 (13)
C3—C4—C7	121.24 (14)	C13—C12—H12A	119.3
C6—C5—C4	121.78 (14)	C11—C12—H12A	119.3
C6—C5—H5A	119.1	C14—C13—C12	118.14 (14)
C4—C5—H5A	119.1	C14—C13—H13A	120.9
C5—C6—C1	120.55 (13)	C12—C13—H13A	120.9
C5—C6—H6A	119.7	F1—C14—C15	118.83 (13)
C1—C6—H6A	119.7	F1—C14—C13	118.27 (14)
C4—C7—H7A	109.5	C15—C14—C13	122.90 (14)
C4—C7—H7B	109.5	C14—C15—C16	117.83 (14)
H7A—C7—H7B	109.5	C14—C15—H15A	121.1
C4—C7—H7C	109.5	C16—C15—H15A	121.1
H7A—C7—H7C	109.5	C15—C16—C11	122.06 (14)
H7B—C7—H7C	109.5	C15—C16—H16A	119.0
O1—C8—C9	120.57 (12)	C11—C16—H16A	119.0
O1—C8—C1	120.07 (12)
C6—C1—C2—C3	0.52 (19)	C1—C8—C9—C10	159.24 (13)
C8—C1—C2—C3	179.32 (12)	C8—C9—C10—C11	178.29 (12)
C1—C2—C3—C4	0.4 (2)	C9—C10—C11—C16	169.98 (15)
C2—C3—C4—C5	−1.3 (2)	C9—C10—C11—C12	−12.7 (2)
C2—C3—C4—C7	178.75 (14)	C16—C11—C12—C13	0.2 (2)
C3—C4—C5—C6	1.2 (2)	C10—C11—C12—C13	−177.13 (13)
C7—C4—C5—C6	−178.76 (14)	C11—C12—C13—C14	0.1 (2)
C4—C5—C6—C1	−0.4 (2)	C12—C13—C14—F1	179.15 (12)
C2—C1—C6—C5	−0.5 (2)	C12—C13—C14—C15	−0.9 (2)
C8—C1—C6—C5	−179.28 (13)	F1—C14—C15—C16	−178.74 (12)
C6—C1—C8—O1	−168.27 (14)	C13—C14—C15—C16	1.3 (2)
C2—C1—C8—O1	12.99 (19)	C14—C15—C16—C11	−0.9 (2)
C6—C1—C8—C9	13.7 (2)	C12—C11—C16—C15	0.2 (2)
C2—C1—C8—C9	−165.02 (12)	C10—C11—C16—C15	177.66 (13)
O1—C8—C9—C10	−18.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1^i	0.94	2.53	3.3598 (17)	148

Symmetry code: (i) −x+1, −y+1, −z+1.