2-[2-(Trifluoro­meth­yl)phen­yl]-2H-1-benzopyran-4(3H)-one

Francuski, B.M.; Ivković, B.; Stojanović, I.; Vladimirov, S.; Francuski, D.

doi:10.1107/S160053681201687X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1522

doi:10.1107/S160053681201687X

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2-[2-(Trifluoromethyl)phenyl]-2H-1-benzopyran-4(3H)-one

Bojana M. Francuski,^a Branka Ivković,^b ^* Ivana Stojanović,^b Sote Vladimirov ^b and Djordje Francuski ^c

^aVINČA Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade, PO Box 522, 11001 Belgrade, Serbia, ^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11010 Belgrade, Serbia, and ^cInstitute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11010 Belgrade, Serbia
^*Correspondence e-mail: blucic@pharmacy.bg.ac.rs

(Received 30 March 2012; accepted 17 April 2012; online 25 April 2012)

In the title compound, C₁₆H₁₁F₃O₂, the γ-pyranone ring adopts an envelope conformation with the chiral C atom standing out of the ring plane. In the crystal, molecules are linked by C—H⋯O and C—H⋯F interactions.

Related literature

For general background to flavones, see: Harborne & Williams (2000 ). For related flavonoids, see: Benavente-García & Castillo (2008 ); Rodeiro et al. (2006 ). For related structures, see: Wera et al. (2012 ); Białońska et al. (2007 ); Krishnaiah et al. (2005 ); Wu et al. (2005 ). For van der Waals radii, see: Bondi (1964 ).

Experimental

Crystal data

C₁₆H₁₁F₃O₂
M_r = 292.25
Orthorhombic, P n a 2₁
a = 8.2291 (9) Å
b = 22.020 (3) Å
c = 7.3355 (11) Å
V = 1329.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.18 × 0.02 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer
4585 measured reflections
2558 independent reflections
1462 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.087
wR(F²) = 0.109
S = 1.12
2558 reflections
190 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.54	3.311 (5)	140
C5—H5⋯F3ⁱⁱ	0.93	2.54	3.313 (5)	141
Symmetry codes: (i) x+1, y, z; (ii) $[-x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd., Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ), PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681201687X/kj2198sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201687X/kj2198Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201687X/kj2198Isup3.mol

Supporting information file. DOI: 10.1107/S160053681201687X/kj2198Isup4.cml

checkCIF report

Comment top

The title compound belongs to the group of flavanones which occur predominantly in citrus fruits. Citrus flavonoids were reported (Benavente-García & Castillo, 2008) as having antimicrobial, antifungal, antiviral, anti–allergenic, anti-inflammatory (Harborne & Williams, 2000) and antioxidant (Rodeiro et al., 2006) properties. Case control studies suggest that flavonoids may reduce the risk of cardiovascular disease and stroke. Considering the wide spectrum of activities of natural flavonoids further structure modification of these molecules is aimed to enhance their interaction with the target sites in cells.

The title compound adopts a typical conformation of flavanones with the γ–pyranone ring adopting the envelope conformation. In this conformation the carbon atoms C1, C6, C7, C8 and oxygen O1 are nearly coplanar with a root mean square deviation from the mean plane of 0.035 Å, while the C9 carbon atom is standing out from this plane with an atom–to–plane distance of 0.652 (6) Å. All bond lengths and angles in the title compound show usual values for this type of compounds (Wera et al., 2012; Białońska et al., 2007; Krishnaiah et al., 2005; Wu et al., 2005). In this crystal packing of the title compound there are 4 intramolecular, 2 intermolecular (C—H···O and C—H···F) and one π–π interaction. All of the fluoride atoms participate in weak intramolecular C—H···F interactions (Fig. 1) with H···F distances equal or shorter than 2.50 Å, which is shorter than the sum of their Van der Waals radii (Bondi, 1964). Two of the fluoride atoms interact with the hydrogen atom connected to the chiral carbon atom C9 while the third fluoride atom interacts with one of the phenyl hydrogen atoms (Table 1). The dihedral angle between Cg1 and Cg2 rings in previously published structures of flavanones (Wera et al., 2012; Białońska et al., 2007; Krishnaiah et al., 2005; Wu et al., 2005) is in the range from 55 to 75° while the corresponding dihedral angle in the case of the title compound is 66.06 (15)°.

The flavanone molecules are connected into rows by the C3—H3···O2 intermolecular interaction forming chains down the crystallographic a axis (Fig. 2). The second intermolecular interaction, C5—H5···F3, connects the molecules into another chain in the direction of the screw axis following the crystallographic c axis, thus forming a two dimensional net of molecules (Fig. 3). Strings of molecules along the crystallographic c axis are further connected by π–π interactions (Fig. 4). Perpendicular distance from the centroid of one Cg1 ring, molecule at (x, y, z), to the plane of the second Cg1 ring, molecule at (1 - x, 2 - y, 1/2 + z), and vice versa are 3.70 and 3.62 Å respectively, while the distance between the ring centroids measures 4.101 (3) Å. The Cg1 ring planes of molecules at (x, y, z) and (1 - x, 2 - y, 1/2 + z) are nearly parallel with the dihedral angle being 5.59 (3)°.

Related literature top

For general background to flavones, see: Harborne & Williams (2000). For related flavonoids, see: Benavente-García & Castillo (2008); Rodeiro et al. (2006). For related structures, see: Wera et al. (2012); Białońska et al. (2007); Krishnaiah et al. (2005); Wu et al. (2005). For van der Waals radii, see: Bondi (1964).

Experimental top

The proposed compound was prepared in two steps. The first step in the synthetic route consisted of the condensation of 2-hydroxy acetophenone with 2-trifluoromethylbenzaldehyde to give an α,β-unsaturated ketone (chalcone). In the second step the obtained chalcone was dissolved under stirring in a 50:50 water/ethanol mixture. The pH was set to 9.0 with 0.1 M NaOH and the reaction mixture was refluxed for 2 h after which it was cooled over night to room temperature. Small crystals of the title compound formed in the reaction vessel and, after draining excess fluid, the crystals were dried at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non–H atoms. H atoms are represented as small spheres of arbitrary radii. Intramolecular interactions are shown as dashed lines.
	Fig. 2. Molecular packing of the title compound and intermolecular interactions along the crystallographic a axis.
	Fig. 3. Molecular packing of the title compound and intermolecular interactions along the crystallographic c axis.
	Fig. 4. π–π interactions of two neighbouring Cg1 rings. Symmetry code: (i) 1 - x, 2 - y, 1/2 + z.

2-[2-(Trifluoromethyl)phenyl]-2H-1-benzopyran-4(3H)-one top

Crystal data top

C₁₆H₁₁F₃O₂	F(000) = 600
M_r = 292.25	D_x = 1.460 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 966 reflections
a = 8.2291 (9) Å	θ = 3.3–28.9°
b = 22.020 (3) Å	µ = 0.12 mm⁻¹
c = 7.3355 (11) Å	T = 293 K
V = 1329.2 (3) Å³	Needle, colourless
Z = 4	0.18 × 0.02 × 0.02 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	1462 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.049
Graphite monochromator	θ_max = 28.9°, θ_min = 3.7°
Detector resolution: 16.3280 pixels mm^-1	h = −11→10
ω scans	k = −28→29
4585 measured reflections	l = −9→9
2558 independent reflections

Refinement top

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.025P)²] where P = (F_o² + 2F_c²)/3
2558 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₆H₁₁F₃O₂	V = 1329.2 (3) Å³
M_r = 292.25	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 8.2291 (9) Å	µ = 0.12 mm⁻¹
b = 22.020 (3) Å	T = 293 K
c = 7.3355 (11) Å	0.18 × 0.02 × 0.02 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	1462 reflections with I > 2σ(I)
4585 measured reflections	R_int = 0.049
2558 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.087	1 restraint
wR(F²) = 0.109	H-atom parameters constrained
S = 1.12	Δρ_max = 0.16 e Å⁻³
2558 reflections	Δρ_min = −0.15 e Å⁻³
190 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

	x	y	z	U_iso*/U_eq
O1	0.3661 (3)	0.90660 (11)	0.7245 (5)	0.0481 (8)
O2	−0.0253 (3)	1.02162 (14)	0.7338 (6)	0.0901 (14)
F1	0.0147 (4)	0.74844 (13)	0.3065 (5)	0.1002 (11)
F2	0.1886 (3)	0.82036 (13)	0.2974 (4)	0.0759 (8)
F3	−0.0440 (3)	0.83559 (15)	0.4155 (5)	0.0867 (10)
C1	0.3889 (4)	0.96841 (17)	0.7160 (7)	0.0394 (10)
C2	0.5488 (4)	0.98855 (19)	0.7098 (7)	0.0475 (12)
H2	0.6339	0.9608	0.7105	0.057*
C3	0.5801 (5)	1.04910 (19)	0.7029 (7)	0.0496 (12)
H3	0.6872	1.0626	0.7023	0.060*
C4	0.4543 (5)	1.09121 (19)	0.6967 (7)	0.0581 (13)
H4	0.4767	1.1325	0.6878	0.070*
C5	0.2973 (5)	1.07110 (18)	0.7040 (7)	0.0557 (13)
H5	0.2132	1.0993	0.7028	0.067*
C6	0.2595 (4)	1.00912 (18)	0.7131 (7)	0.0416 (11)
C7	0.0917 (5)	0.98787 (19)	0.7367 (8)	0.0563 (14)
C8	0.0756 (4)	0.92045 (17)	0.7675 (7)	0.0555 (15)
H8A	−0.0302	0.9070	0.7254	0.067*
H8B	0.0831	0.9119	0.8969	0.067*
C9	0.2082 (4)	0.88567 (18)	0.6662 (6)	0.0393 (11)
H9	0.1964	0.8925	0.5349	0.047*
C10	0.2017 (4)	0.81852 (19)	0.7043 (6)	0.0365 (10)
C11	0.1381 (5)	0.7759 (2)	0.5836 (6)	0.0387 (11)
C12	0.1326 (5)	0.7148 (2)	0.6313 (7)	0.0478 (13)
H12	0.0877	0.6868	0.5509	0.057*
C13	0.1925 (5)	0.6955 (2)	0.7952 (8)	0.0540 (12)
H13	0.1884	0.6545	0.8253	0.065*
C14	0.2581 (5)	0.7360 (2)	0.9145 (7)	0.0583 (14)
H14	0.2998	0.7227	1.0254	0.070*
C15	0.2626 (5)	0.7976 (2)	0.8697 (7)	0.0505 (13)
H15	0.3071	0.8252	0.9518	0.061*
C16	0.0756 (6)	0.7942 (2)	0.4026 (8)	0.0594 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0319 (14)	0.0360 (17)	0.076 (2)	−0.0008 (13)	−0.0020 (16)	0.001 (2)
O2	0.0468 (16)	0.064 (2)	0.160 (4)	0.0188 (17)	0.013 (2)	0.002 (3)
F1	0.149 (3)	0.079 (2)	0.072 (2)	−0.041 (2)	−0.051 (2)	−0.002 (2)
F2	0.0938 (18)	0.087 (2)	0.0464 (17)	−0.0169 (17)	0.0070 (17)	0.0086 (19)
F3	0.0697 (18)	0.097 (2)	0.093 (2)	0.0126 (19)	−0.0212 (18)	0.022 (2)
C1	0.044 (2)	0.032 (2)	0.042 (3)	−0.002 (2)	0.007 (2)	−0.009 (3)
C2	0.035 (2)	0.046 (3)	0.062 (3)	0.000 (2)	0.007 (3)	0.001 (3)
C3	0.050 (2)	0.045 (3)	0.055 (3)	−0.011 (2)	0.006 (3)	0.005 (3)
C4	0.070 (3)	0.031 (2)	0.073 (4)	−0.011 (3)	0.018 (3)	−0.005 (3)
C5	0.060 (3)	0.036 (3)	0.071 (3)	0.009 (2)	0.010 (3)	−0.001 (3)
C6	0.041 (2)	0.036 (3)	0.049 (3)	0.002 (2)	0.005 (3)	−0.002 (3)
C7	0.047 (2)	0.047 (3)	0.076 (4)	0.002 (2)	0.006 (3)	−0.013 (4)
C8	0.037 (2)	0.045 (3)	0.085 (4)	−0.002 (2)	0.009 (3)	−0.004 (3)
C9	0.040 (2)	0.042 (2)	0.036 (3)	−0.003 (2)	0.005 (2)	−0.007 (2)
C10	0.0344 (19)	0.037 (3)	0.038 (3)	−0.005 (2)	0.001 (2)	0.002 (3)
C11	0.030 (2)	0.044 (3)	0.042 (3)	−0.001 (2)	−0.002 (2)	0.002 (3)
C12	0.056 (3)	0.041 (3)	0.046 (3)	−0.001 (3)	0.004 (2)	−0.005 (3)
C13	0.060 (3)	0.035 (3)	0.067 (3)	−0.004 (3)	0.005 (3)	0.006 (3)
C14	0.066 (3)	0.060 (4)	0.050 (3)	−0.009 (3)	−0.014 (3)	0.015 (3)
C15	0.061 (3)	0.046 (3)	0.045 (3)	−0.008 (2)	−0.001 (3)	−0.006 (3)
C16	0.060 (3)	0.058 (4)	0.060 (4)	−0.011 (3)	−0.016 (3)	0.001 (4)

Geometric parameters (Å, º) top

O1—C1	1.376 (4)	C7—C8	1.508 (5)
O1—C9	1.443 (4)	C8—C9	1.526 (5)
O2—C7	1.217 (4)	C8—H8A	0.9700
F1—C16	1.328 (5)	C8—H8B	0.9700
F2—C16	1.339 (5)	C9—C10	1.506 (5)
F3—C16	1.345 (5)	C9—H9	0.9800
C1—C2	1.389 (5)	C10—C15	1.391 (5)
C1—C6	1.392 (5)	C10—C11	1.392 (5)
C2—C3	1.359 (5)	C11—C12	1.390 (6)
C2—H2	0.9300	C11—C16	1.480 (7)
C3—C4	1.390 (5)	C12—C13	1.367 (6)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.367 (5)	C13—C14	1.361 (6)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.401 (5)	C14—C15	1.397 (6)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.468 (5)	C15—H15	0.9300

C1—O1—C9	115.2 (3)	O1—C9—C8	109.8 (3)
O1—C1—C2	116.5 (3)	C10—C9—C8	112.2 (3)
O1—C1—C6	122.3 (3)	O1—C9—H9	109.3
C2—C1—C6	121.2 (3)	C10—C9—H9	109.3
C3—C2—C1	119.6 (4)	C8—C9—H9	109.3
C3—C2—H2	120.2	C15—C10—C11	117.9 (4)
C1—C2—H2	120.2	C15—C10—C9	118.3 (4)
C2—C3—C4	121.0 (4)	C11—C10—C9	123.9 (4)
C2—C3—H3	119.5	C12—C11—C10	120.3 (4)
C4—C3—H3	119.5	C12—C11—C16	118.5 (4)
C5—C4—C3	119.1 (4)	C10—C11—C16	121.2 (4)
C5—C4—H4	120.4	C13—C12—C11	120.7 (5)
C3—C4—H4	120.4	C13—C12—H12	119.7
C4—C5—C6	121.8 (4)	C11—C12—H12	119.7
C4—C5—H5	119.1	C14—C13—C12	120.3 (5)
C6—C5—H5	119.1	C14—C13—H13	119.8
C1—C6—C5	117.3 (3)	C12—C13—H13	119.8
C1—C6—C7	120.8 (4)	C13—C14—C15	119.7 (5)
C5—C6—C7	121.6 (4)	C13—C14—H14	120.1
O2—C7—C6	123.2 (4)	C15—C14—H14	120.1
O2—C7—C8	122.3 (4)	C10—C15—C14	121.1 (4)
C6—C7—C8	114.5 (4)	C10—C15—H15	119.4
C7—C8—C9	111.0 (3)	C14—C15—H15	119.4
C7—C8—H8A	109.4	F1—C16—F2	106.4 (5)
C9—C8—H8A	109.4	F1—C16—F3	106.0 (4)
C7—C8—H8B	109.4	F2—C16—F3	104.9 (4)
C9—C8—H8B	109.4	F1—C16—C11	113.7 (4)
H8A—C8—H8B	108.0	F2—C16—C11	113.2 (4)
O1—C9—C10	106.9 (3)	F3—C16—C11	112.0 (5)

C9—O1—C1—C2	−158.8 (4)	C7—C8—C9—C10	176.3 (4)
C9—O1—C1—C6	21.0 (7)	O1—C9—C10—C15	43.2 (5)
O1—C1—C2—C3	−179.4 (5)	C8—C9—C10—C15	−77.3 (5)
C6—C1—C2—C3	0.7 (8)	O1—C9—C10—C11	−136.9 (4)
C1—C2—C3—C4	−1.8 (8)	C8—C9—C10—C11	102.7 (4)
C2—C3—C4—C5	2.2 (8)	C15—C10—C11—C12	1.7 (6)
C3—C4—C5—C6	−1.6 (8)	C9—C10—C11—C12	−178.2 (4)
O1—C1—C6—C5	−179.9 (4)	C15—C10—C11—C16	−178.1 (4)
C2—C1—C6—C5	−0.1 (7)	C9—C10—C11—C16	2.0 (6)
O1—C1—C6—C7	5.9 (7)	C10—C11—C12—C13	−1.4 (6)
C2—C1—C6—C7	−174.3 (5)	C16—C11—C12—C13	178.4 (4)
C4—C5—C6—C1	0.5 (8)	C11—C12—C13—C14	0.2 (7)
C4—C5—C6—C7	174.7 (5)	C12—C13—C14—C15	0.7 (7)
C1—C6—C7—O2	−179.4 (6)	C11—C10—C15—C14	−0.9 (6)
C5—C6—C7—O2	6.6 (9)	C9—C10—C15—C14	179.1 (4)
C1—C6—C7—C8	1.3 (7)	C13—C14—C15—C10	−0.3 (7)
C5—C6—C7—C8	−172.6 (5)	C12—C11—C16—F1	2.2 (7)
O2—C7—C8—C9	148.5 (5)	C10—C11—C16—F1	−178.0 (4)
C6—C7—C8—C9	−32.3 (6)	C12—C11—C16—F2	−119.4 (4)
C1—O1—C9—C10	−174.2 (4)	C10—C11—C16—F2	60.4 (6)
C1—O1—C9—C8	−52.2 (5)	C12—C11—C16—F3	122.3 (4)
C7—C8—C9—O1	57.6 (5)	C10—C11—C16—F3	−57.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···F2	0.98	2.36	3.068 (5)	129
C9—H9···F3	0.98	2.50	2.984 (5)	110
C12—H12···F1	0.93	2.33	2.677 (6)	102
C15—H15···O1	0.93	2.50	2.760 (5)	96
C3—H3···O2ⁱ	0.93	2.54	3.311 (5)	140
C5—H5···F3ⁱⁱ	0.93	2.54	3.313 (5)	141

Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁F₃O₂
M_r	292.25
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	8.2291 (9), 22.020 (3), 7.3355 (11)
V (Å³)	1329.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.18 × 0.02 × 0.02

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4585, 2558, 1462
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.680

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.087, 0.109, 1.12
No. of reflections	2558
No. of parameters	190
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···F2	0.98	2.36	3.068 (5)	129
C9—H9···F3	0.98	2.50	2.984 (5)	110
C12—H12···F1	0.93	2.33	2.677 (6)	102
C15—H15···O1	0.93	2.50	2.760 (5)	96
C3—H3···O2ⁱ	0.93	2.54	3.311 (5)	140
C5—H5···F3ⁱⁱ	0.93	2.54	3.313 (5)	141

Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, z+1/2.

Acknowledgements

We would like to thank Dr Vladimir Divjaković and Dr Agneš Kapor for the data acquisition and Dr Goran A. Bogdanović for his valuable suggestions. Our work was supported by Scientific Research Grants from the Serbian Ministry of Science and Technology (grant Nos. OI172041, ON172035 and ON173008).

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