2-Hy­droxy-2-trifluoro­methyl-3,4-dihydro-2H-1-benzopyran-4-one

Abdullah M Asiri; Hassan M Faidallah; Khalid A Alamry; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812029170

. 2012 Jun 30;68(Pt 7):o2299. doi: 10.1107/S1600536812029170

2-Hydroxy-2-trifluoromethyl-3,4-dihydro-2H-1-benzopyran-4-one

Abdullah M Asiri ^a,^b,^‡, Hassan M Faidallah ^b, Khalid A Alamry ^a,^b, Seik Weng Ng ^c, Edward R T Tiekink ^c,^*

PMCID: PMC3394075 PMID: 22798940

Abstract

The heterocyclic ring in the title compound, C₁₀H₇F₃O₃, has a half-boat conformation with the hydroxy-bearing C atom lying 0.595 (3) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.022 Å) in the direction of the hydroxy O atom. Linear supramolecular chains along the a axis, sustained by O—H⋯O hydrogen bonds between the hydroxy H and ketone O atoms, feature in the crystal packing. These chains are connected into a three-dimensional architecture by C—H⋯O and C—H⋯F contacts.

Related literature

For an example of an anticipated product formed between the reaction of bis(ethylidene)ethane-1,2-diamine with an anhydride, see: Asiri et al. (2011 ▶). For the crystal structure of a related compound, see: Wang et al. (1999 ▶).

Experimental

Crystal data

C₁₀H₇F₃O₃
M _r = 232.16
Triclinic,
a = 5.9516 (5) Å
b = 8.5188 (7) Å
c = 10.2036 (8) Å
α = 66.985 (8)°
β = 80.380 (7)°
γ = 78.311 (7)°
V = 464.05 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.528, T _max = 1.000
3161 measured reflections
2126 independent reflections
1665 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.171
S = 1.06
2126 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029170/su2468sup1.cif

e-68-o2299-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029170/su2468Isup2.hkl

e-68-o2299-Isup2.hkl^{(104.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812029170/su2468Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O2ⁱ	0.86 (3)	1.97 (3)	2.768 (2)	154 (3)
C2—H2⋯O1ⁱⁱ	0.95	2.60	3.444 (3)	148
C3—H3⋯F3ⁱⁱⁱ	0.95	2.52	3.338 (3)	144
C8—H8A⋯F1^iv	0.99	2.51	3.033 (2)	113
C8—H8B⋯O3^v	0.99	2.56	3.547 (2)	175

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

The authors are grateful to King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

The title compound, (I), was isolated unexpectedly from a reaction between N,N'-bis[1-(p-hydroxyhenyl)ethylidene]ethane-1,2-diamine and trifluoroacetic anhydride to yield the anticipated di-substituted ethylenediamine derivative in accord with literature precedents (Asiri et al., 2011).

In (I), Fig. 1, the heterocyclic ring has a half-boat conformation with the hydroxy bearing C9 atom lying 0.595 (3) Å out of the plane of the five remaining atoms [r.m.s. deviation = 0.022 Å] in the direction of the hydroxy O3 atom. A similar conformation was found in a literature precedent with phenyl rather than CF₃ and with OH and two OMe substituents on the benzene ring (Wang et al., 1999).

In the crystal, linear supramolecular chains sustained by O—H···O hydrogen bonds between the hydroxy H and ketone-O atoms (Table 1), are formed along the a axis (Fig. 2). These are connected into a three-dimensional architecture by C—H···O and C—H···F contacts (Fig. 3 and Table 1).

Experimental

A mixture of N,N'-bis[1-(p-hydroxyhenyl)ethylidene]ethane-1,2-diamine (0.01 M) in THF (30 ml) and trifluoroacetic anhydride (0.025 M) was refluxed for 2 h. The solid which separated on cooling was recrystallized from its ethanol solution. M. pt: 477–478 K. Yield: 70%.