3-(3,5-Difluoro­phen­yl)-1-phenyl­prop-2-en-1-one

The crystal structure of the title compound, C₁₅H₁₀F₂O, shows that the stereochemistry around the C=C double bond in the C=C-CO unit is trans.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.056
• wR factor = 0.122
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         41 Perc.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: Nonius SUPERGUI [Please provide reference]; cell refinement: NDIRAX [Please provide reference]; data reduction: NDIRAX; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(3,5-Difluorophenyl)-1-phenylprop-2-en-1-one

Crystal data

C15H10F2O	Z = 2
Mr = 244.24	F(000) = 252
Triclinic, P1	Dx = 1.344 Mg m^−3
Hall symbol: -P 1	Melting point: 382 K
a = 6.0359 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5002 (15) Å	θ = 1–27.5°
c = 13.637 (3) Å	µ = 0.10 mm^−1
α = 92.80 (3)°	T = 293 K
β = 96.10 (3)°	Block, colourless
γ = 99.82 (3)°	0.30 × 0.20 × 0.15 mm
V = 603.5 (2) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	910 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.079
Graphite monochromator	θmax = 25.5°, θmin = 5.1°
φ scans, and ω scans with κ offset	h = −7→7
5771 measured reflections	k = −9→8
2222 independent reflections	l = −16→16

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0495P)^2] where P = (Fo^2 + 2Fc^2)/3
2222 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.15 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.8048 (0.0226) x + 6.9580 (0.0130) y + 2.6690 (0.0314) z = 1.6648 (0.0126)

* 0.0000 (0.0000) C1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C3

Rms deviation of fitted atoms = 0.0000

- 2.8314 (0.0057) x + 7.0334 (0.0046) y + 1.8883 (0.0139) z = 1.3363 (0.0045)

Angle to previous plane (with approximate e.s.d.) = 3.35 (0.34)

* -0.0083 (0.0018) C11 * 0.0026 (0.0018) C12 * 0.0042 (0.0019) C13 * -0.0052 (0.0020) C14 * -0.0006 (0.0019) C15 * 0.0072 (0.0017) C16

Rms deviation of fitted atoms = 0.0054

- 2.4737 (0.0102) x + 7.1133 (0.0069) y + 2.3751 (0.0268) z = 1.7678 (0.0104)

Angle to previous plane (with approximate e.s.d.) = 4.39 (0.17)

* -0.0130 (0.0008) O1 * 0.0246 (0.0015) C1 * -0.0241 (0.0015) C2 * 0.0126 (0.0008) C3

Rms deviation of fitted atoms = 0.0194

- 2.0410 (0.0069) x + 7.2830 (0.0044) y + 1.8310 (0.0158) z = 1.8491 (0.0139)

Angle to previous plane (with approximate e.s.d.) = 4.90 (0.16)

* 0.0000 (0.0018) C21 * -0.0028 (0.0022) C22 * 0.0019 (0.0024) C23 * 0.0018 (0.0024) C24 * -0.0046 (0.0024) C25 * 0.0037 (0.0021) C26

Rms deviation of fitted atoms = 0.0029

- 2.8314 (0.0057) x + 7.0334 (0.0046) y + 1.8883 (0.0139) z = 1.3363 (0.0045)

Angle to previous plane (with approximate e.s.d.) = 8.21 (0.11)

* -0.0083 (0.0018) C11 * 0.0026 (0.0018) C12 * 0.0042 (0.0019) C13 * -0.0052 (0.0020) C14 * -0.0006 (0.0019) C15 * 0.0072 (0.0017) C16

Rms deviation of fitted atoms = 0.0054

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
C1	0.8182 (4)	0.3177 (3)	0.65539 (19)	0.0572 (7)
C2	0.6251 (4)	0.2694 (3)	0.57814 (18)	0.0568 (7)
H2	0.4892	0.2080	0.5955	0.068*
C3	0.6350 (4)	0.3090 (3)	0.48527 (19)	0.0550 (7)
H3	0.7725	0.3731	0.4711	0.066*
C11	0.4568 (4)	0.2648 (3)	0.40177 (18)	0.0504 (7)
C12	0.5074 (5)	0.3125 (4)	0.3071 (2)	0.0595 (7)
C13	0.3427 (5)	0.2671 (4)	0.22886 (19)	0.0690 (8)
C14	0.1287 (5)	0.1773 (4)	0.2376 (2)	0.0725 (8)
H14	0.0196	0.1467	0.1832	0.087*
C15	0.0844 (5)	0.1350 (4)	0.3311 (2)	0.0669 (8)
C16	0.2397 (4)	0.1765 (3)	0.41326 (19)	0.0581 (7)
H16	0.2011	0.1464	0.4754	0.070*
C21	0.7903 (4)	0.2839 (3)	0.76174 (18)	0.0507 (6)
C22	0.5845 (5)	0.2177 (4)	0.7937 (2)	0.0702 (8)
H22	0.4550	0.1920	0.7483	0.084*
C23	0.5680 (5)	0.1890 (5)	0.8924 (2)	0.0914 (10)
H23	0.4281	0.1451	0.9130	0.110*
C24	0.7562 (6)	0.2250 (5)	0.9591 (2)	0.0945 (11)
H24	0.7446	0.2057	1.0254	0.113*
C25	0.9635 (6)	0.2896 (5)	0.9293 (2)	0.0915 (10)
H25	1.0924	0.3129	0.9751	0.110*
C26	0.9796 (4)	0.3201 (4)	0.8306 (2)	0.0707 (8)
H26	1.1197	0.3655	0.8107	0.085*
F1	0.3947 (3)	0.3115 (3)	0.13626 (12)	0.1083 (7)
F2	−0.1259 (3)	0.0443 (2)	0.34343 (13)	0.0987 (6)
O1	1.0039 (3)	0.3846 (3)	0.63268 (13)	0.0946 (7)
H12	0.660 (4)	0.372 (3)	0.2958 (17)	0.073 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0505 (16)	0.0617 (18)	0.0555 (18)	−0.0012 (13)	0.0034 (13)	0.0107 (14)
C2	0.0541 (17)	0.0650 (19)	0.0479 (16)	0.0004 (13)	0.0034 (13)	0.0093 (14)
C3	0.0511 (15)	0.0577 (18)	0.0544 (17)	0.0042 (12)	0.0043 (13)	0.0085 (13)
C11	0.0513 (16)	0.0480 (16)	0.0518 (17)	0.0101 (12)	0.0026 (13)	0.0045 (13)
C12	0.0630 (19)	0.0595 (18)	0.0556 (19)	0.0080 (15)	0.0079 (15)	0.0075 (14)
C13	0.093 (2)	0.072 (2)	0.0414 (18)	0.0186 (18)	0.0000 (16)	0.0065 (15)
C14	0.078 (2)	0.069 (2)	0.064 (2)	0.0172 (17)	−0.0205 (16)	−0.0067 (17)
C15	0.0554 (19)	0.067 (2)	0.073 (2)	0.0070 (15)	−0.0076 (16)	−0.0015 (16)
C16	0.0589 (17)	0.0625 (18)	0.0535 (17)	0.0128 (14)	0.0058 (14)	0.0047 (13)
C21	0.0516 (16)	0.0512 (16)	0.0478 (15)	0.0075 (12)	0.0001 (13)	0.0062 (12)
C22	0.0587 (18)	0.090 (2)	0.0589 (19)	0.0018 (15)	0.0047 (14)	0.0154 (16)
C23	0.072 (2)	0.138 (3)	0.064 (2)	0.0094 (19)	0.0136 (17)	0.026 (2)
C24	0.099 (3)	0.135 (3)	0.0535 (19)	0.030 (2)	0.007 (2)	0.0183 (19)
C25	0.078 (2)	0.133 (3)	0.059 (2)	0.016 (2)	−0.0086 (17)	0.0089 (19)
C26	0.0575 (18)	0.093 (2)	0.0575 (18)	0.0060 (15)	0.0005 (15)	0.0072 (16)
F1	0.1340 (16)	0.1366 (17)	0.0501 (11)	0.0139 (12)	0.0021 (10)	0.0186 (10)
F2	0.0590 (11)	0.1153 (15)	0.1101 (14)	−0.0047 (9)	−0.0082 (9)	0.0021 (11)
O1	0.0619 (13)	0.1411 (19)	0.0685 (14)	−0.0191 (12)	0.0024 (10)	0.0285 (12)

Geometric parameters (Å, º)

C1—O1	1.225 (3)	C14—H14	0.9300
C1—C2	1.469 (3)	C15—F2	1.365 (3)
C1—C21	1.506 (3)	C15—C16	1.369 (3)
C2—C3	1.320 (3)	C16—H16	0.9300
C2—H2	0.9300	C21—C26	1.380 (3)
C3—C11	1.464 (3)	C21—C22	1.381 (3)
C3—H3	0.9300	C22—C23	1.384 (4)
C11—C16	1.392 (3)	C22—H22	0.9300
C11—C12	1.407 (3)	C23—C24	1.357 (4)
C12—C13	1.366 (4)	C23—H23	0.9300
C12—O1^i	3.400 (4)	C24—C25	1.374 (4)
C12—H12	0.98 (2)	C24—H24	0.9300
C13—C14	1.372 (4)	C25—C26	1.387 (4)
C13—F1	1.376 (3)	C25—H25	0.9300
C14—C15	1.372 (4)	C26—H26	0.9300
O1—C1—C2	119.5 (2)	F2—C15—C14	118.4 (3)
O1—C1—C21	119.9 (2)	C16—C15—C14	123.9 (3)
C2—C1—C21	120.6 (2)	C15—C16—C11	118.5 (3)
C3—C2—C1	123.3 (2)	C15—C16—H16	120.7
C3—C2—H2	118.4	C11—C16—H16	120.7
C1—C2—H2	118.4	C26—C21—C22	118.3 (3)
C2—C3—C11	128.2 (2)	C26—C21—C1	118.5 (2)
C2—C3—H3	115.9	C22—C21—C1	123.2 (2)
C11—C3—H3	115.9	C21—C22—C23	120.9 (3)
C16—C11—C12	119.1 (2)	C21—C22—H22	119.5
C16—C11—C3	122.0 (2)	C23—C22—H22	119.5
C12—C11—C3	118.9 (2)	C24—C23—C22	120.0 (3)
C13—C12—C11	118.8 (3)	C24—C23—H23	120.0
C13—C12—O1^i	138.4 (2)	C22—C23—H23	120.0
C11—C12—O1^i	100.35 (18)	C23—C24—C25	120.4 (3)
C13—C12—H12	119.7 (14)	C23—C24—H24	119.8
C11—C12—H12	121.4 (14)	C25—C24—H24	119.8
C12—C13—C14	123.3 (3)	C24—C25—C26	119.7 (3)
C12—C13—F1	118.5 (3)	C24—C25—H25	120.2
C14—C13—F1	118.2 (3)	C26—C25—H25	120.2
C15—C14—C13	116.3 (3)	C21—C26—C25	120.8 (3)
C15—C14—H14	121.9	C21—C26—H26	119.6
C13—C14—H14	121.9	C25—C26—H26	119.6
F2—C15—C16	117.7 (3)
O1—C1—C2—C3	−6.2 (4)	F2—C15—C16—C11	178.4 (2)
C21—C1—C2—C3	174.4 (3)	C14—C15—C16—C11	−0.9 (4)
C1—C2—C3—C11	178.5 (2)	C12—C11—C16—C15	1.7 (4)
C2—C3—C11—C16	2.9 (4)	C3—C11—C16—C15	−178.0 (2)
C2—C3—C11—C12	−176.8 (3)	O1—C1—C21—C26	−3.7 (4)
C16—C11—C12—C13	−1.3 (4)	C2—C1—C21—C26	175.7 (2)
C3—C11—C12—C13	178.4 (2)	O1—C1—C21—C22	176.6 (3)
C16—C11—C12—O1^i	164.17 (19)	C2—C1—C21—C22	−4.0 (4)
C3—C11—C12—O1^i	−16.1 (2)	C26—C21—C22—C23	0.3 (4)
C11—C12—C13—C14	0.2 (4)	C1—C21—C22—C23	180.0 (3)
O1^i—C12—C13—C14	−158.1 (2)	C21—C22—C23—C24	−0.4 (5)
C11—C12—C13—F1	−178.9 (2)	C22—C23—C24—C25	−0.1 (5)
O1^i—C12—C13—F1	22.9 (4)	C23—C24—C25—C26	0.7 (5)
C12—C13—C14—C15	0.7 (4)	C22—C21—C26—C25	0.4 (4)
F1—C13—C14—C15	179.7 (2)	C1—C21—C26—C25	−179.3 (3)
C13—C14—C15—F2	−179.5 (2)	C24—C25—C26—C21	−0.9 (5)
C13—C14—C15—C16	−0.3 (4)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1^i	0.98 (2)	2.56 (2)	3.400 (4)	143 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.