Crystal structure of (E)-4,4,4-tri­fluoro-3-phenyl­but-2-enoic acid

Barkov, A.

doi:10.1107/S2056989015023725

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Page o1090

https://doi.org/10.1107/S2056989015023725

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Crystal structure of (E)-4,4,4-trifluoro-3-phenylbut-2-enoic acid

Alexey Barkov ^a ^*

^aDepartment of Chemistry, Institute of Natural Sciences, Ural Federal University, pr. Lenina 51, 620000 Ekaterinburg, Russian Federation
^*Correspondence e-mail: alexey0077@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 19 October 2015; accepted 10 December 2015; online 31 December 2015)

In the title compound, C₁₀H₇F₃O₂, the dihedral angle between the benzene ring and the ethylene plane is 76.34 (11)°. In the crystal, O—H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [010].

Keywords: crystal structure; trifluoromethyl acid; hydrogen bonding.

CCDC reference: 1441578

1. Scheme

The title compound is shown below.

2. Experimental

2.1. Crystal data

C₁₀H₇F₃O₂
M_r = 216.16
Monoclinic, P 2₁ /c
a = 11.4093 (9) Å
b = 5.7749 (4) Å
c = 14.7469 (8) Å
β = 96.300 (6)°
V = 965.77 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 295 K
0.25 × 0.12 × 0.03 mm

2.2. Data collection

Agilent Xcalibur, Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.835, T_max = 1.000
3799 measured reflections
1960 independent reflections
1252 reflections with I > 2σ(I)
R_int = 0.022

2.3. Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.171
S = 1.02
1960 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.97 (3)	1.77 (3)	2.715 (2)	166 (3)
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1441578

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023725/hb7527sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015023725/hb7527Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015023725/hb7527Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989015023725/hb7527Isup4.cml

checkCIF report

Related literature top

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Structure description top

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Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. Ellipsoid plot.

(E)-4,4,4-Trifluoro-3-phenylbut-2-enoic acid top

Crystal data top

C₁₀H₇F₃O₂	F(000) = 440
M_r = 216.16	D_x = 1.487 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
a = 11.4093 (9) Å	Cell parameters from 816 reflections
b = 5.7749 (4) Å	θ = 2.8–24.2°
c = 14.7469 (8) Å	µ = 0.14 mm⁻¹
β = 96.300 (6)°	T = 295 K
V = 965.77 (11) Å³	Plate, colourless
Z = 4	0.25 × 0.12 × 0.03 mm

Data collection top

Agilent Xcalibur, Eos diffractometer	1960 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1252 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 15.9555 pixels mm^-1	θ_max = 26.4°, θ_min = 1.8°
ω scans	h = −14→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −7→6
T_min = 0.835, T_max = 1.000	l = −18→18
3799 measured reflections

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
1960 reflections	(Δ/σ)_max < 0.001
140 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₀H₇F₃O₂	V = 965.77 (11) Å³
M_r = 216.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4093 (9) Å	µ = 0.14 mm⁻¹
b = 5.7749 (4) Å	T = 295 K
c = 14.7469 (8) Å	0.25 × 0.12 × 0.03 mm
β = 96.300 (6)°

Data collection top

Agilent Xcalibur, Eos diffractometer	1960 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	1252 reflections with I > 2σ(I)
T_min = 0.835, T_max = 1.000	R_int = 0.022
3799 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.17 e Å⁻³
1960 reflections	Δρ_min = −0.25 e Å⁻³
140 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
F1	0.33889 (15)	0.9642 (4)	0.53424 (11)	0.0878 (6)
F2	0.16331 (17)	1.0064 (3)	0.47259 (11)	0.0956 (7)
F3	0.23597 (19)	1.2390 (3)	0.57582 (12)	0.0938 (6)
O1	−0.01828 (17)	0.4089 (3)	0.62622 (12)	0.0651 (6)
H1	−0.042 (3)	0.311 (6)	0.674 (2)	0.101 (11)*
O2	0.06645 (14)	0.5790 (3)	0.75208 (10)	0.0510 (5)
C1	0.04817 (19)	0.5707 (4)	0.66953 (15)	0.0439 (6)
C2	0.0965 (2)	0.7311 (4)	0.60493 (15)	0.0484 (6)
H2	0.0581	0.7394	0.5460	0.058*
C3	0.19045 (19)	0.8642 (4)	0.62488 (14)	0.0435 (5)
C4	0.2304 (2)	1.0167 (5)	0.55131 (17)	0.0565 (7)
C5	0.26860 (18)	0.8691 (4)	0.71297 (14)	0.0408 (5)
C6	0.3474 (2)	0.6892 (4)	0.73361 (17)	0.0536 (6)
H6	0.3493	0.5657	0.6933	0.064*
C7	0.4226 (2)	0.6914 (5)	0.81282 (19)	0.0683 (8)
H7	0.4753	0.5699	0.8258	0.082*
C8	0.4205 (3)	0.8706 (6)	0.87260 (18)	0.0703 (8)
H8	0.4713	0.8706	0.9264	0.084*
C9	0.3438 (3)	1.0505 (5)	0.85370 (18)	0.0719 (8)
H9	0.3428	1.1728	0.8947	0.086*
C10	0.2672 (2)	1.0519 (4)	0.77358 (17)	0.0555 (7)
H10	0.2153	1.1748	0.7608	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0745 (12)	0.1200 (16)	0.0741 (11)	−0.0052 (10)	0.0318 (9)	0.0103 (10)
F2	0.1015 (14)	0.1180 (16)	0.0611 (10)	−0.0450 (11)	−0.0194 (9)	0.0354 (10)
F3	0.1397 (17)	0.0535 (10)	0.0926 (13)	−0.0185 (10)	0.0318 (11)	0.0081 (10)
O1	0.0751 (13)	0.0738 (13)	0.0452 (9)	−0.0342 (10)	0.0011 (8)	0.0002 (9)
O2	0.0586 (11)	0.0528 (10)	0.0413 (9)	−0.0007 (7)	0.0039 (7)	−0.0017 (7)
C1	0.0409 (13)	0.0449 (13)	0.0454 (12)	0.0004 (9)	0.0022 (9)	−0.0006 (10)
C2	0.0481 (14)	0.0533 (14)	0.0424 (11)	−0.0035 (11)	−0.0016 (9)	0.0031 (11)
C3	0.0436 (13)	0.0414 (12)	0.0452 (12)	0.0013 (10)	0.0039 (9)	0.0006 (10)
C4	0.0573 (16)	0.0594 (16)	0.0526 (14)	−0.0103 (12)	0.0050 (11)	0.0034 (12)
C5	0.0394 (12)	0.0399 (12)	0.0435 (11)	−0.0034 (9)	0.0068 (9)	−0.0021 (10)
C6	0.0513 (14)	0.0470 (14)	0.0605 (14)	0.0025 (11)	−0.0030 (11)	−0.0087 (12)
C7	0.0594 (17)	0.0656 (18)	0.0750 (18)	0.0028 (13)	−0.0138 (13)	0.0047 (16)
C8	0.0666 (19)	0.087 (2)	0.0536 (15)	−0.0150 (17)	−0.0080 (13)	0.0038 (16)
C9	0.084 (2)	0.077 (2)	0.0546 (15)	−0.0144 (17)	0.0094 (14)	−0.0261 (15)
C10	0.0611 (16)	0.0498 (14)	0.0566 (14)	0.0052 (12)	0.0114 (11)	−0.0091 (12)

Geometric parameters (Å, º) top

F1—C4	1.326 (3)	C5—C6	1.386 (3)
F2—C4	1.320 (3)	C5—C10	1.385 (3)
F3—C4	1.333 (3)	C6—H6	0.9300
O1—H1	0.96 (3)	C6—C7	1.371 (3)
O1—C1	1.323 (3)	C7—H7	0.9300
O2—C1	1.213 (2)	C7—C8	1.361 (4)
C1—C2	1.478 (3)	C8—H8	0.9300
C2—H2	0.9300	C8—C9	1.367 (4)
C2—C3	1.326 (3)	C9—H9	0.9300
C3—C4	1.506 (3)	C9—C10	1.390 (4)
C3—C5	1.493 (3)	C10—H10	0.9300

C1—O1—H1	105.0 (18)	C10—C5—C3	121.9 (2)
O1—C1—C2	111.47 (19)	C10—C5—C6	118.9 (2)
O2—C1—O1	122.6 (2)	C5—C6—H6	119.7
O2—C1—C2	125.9 (2)	C7—C6—C5	120.7 (2)
C1—C2—H2	117.6	C7—C6—H6	119.7
C3—C2—C1	124.7 (2)	C6—C7—H7	119.8
C3—C2—H2	117.6	C8—C7—C6	120.3 (3)
C2—C3—C4	118.7 (2)	C8—C7—H7	119.8
C2—C3—C5	126.5 (2)	C7—C8—H8	119.9
C5—C3—C4	114.63 (19)	C7—C8—C9	120.1 (3)
F1—C4—F3	104.7 (2)	C9—C8—H8	119.9
F1—C4—C3	111.4 (2)	C8—C9—H9	119.8
F2—C4—F1	106.6 (2)	C8—C9—C10	120.4 (2)
F2—C4—F3	106.7 (2)	C10—C9—H9	119.8
F2—C4—C3	114.5 (2)	C5—C10—C9	119.6 (2)
F3—C4—C3	112.2 (2)	C5—C10—H10	120.2
C6—C5—C3	119.22 (19)	C9—C10—H10	120.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.97 (3)	1.77 (3)	2.715 (2)	166 (3)

Symmetry code: (i) −x, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.97 (3)	1.77 (3)	2.715 (2)	166 (3)

Symmetry code: (i) −x, y−1/2, −z+3/2.

Acknowledgements

The work was supported by Act 211 Government of the Russian Federation (contract No. 02.A03.21.0006).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar