N-(2,3,4-Trifluoro­phen­yl)phthalimide

Xian-Shu Fu; Xiao-Ping Yu; Wei-Min Wang; Fang Lin

doi:10.1107/S1600536810024177

. 2010 Jun 30;66(Pt 7):o1859. doi: 10.1107/S1600536810024177

N-(2,3,4-Trifluorophenyl)phthalimide

Xian-Shu Fu ^a, Xiao-Ping Yu ^a, Wei-Min Wang ^a,^*, Fang Lin ^a

PMCID: PMC3006749 PMID: 21588056

Abstract

In the title compound, C₁₄H₆F₃NO₂, the benzene ring and the phthalimide ring system make a dihedral angle of 60.12 (7)°. Weak intermolecular C—H⋯O and C—H⋯F hydrogen bonds are present in the crystal structure.

Related literature

The title compound is a key intermediate in the synthesis of organic electro-luminescent materials, see: Han & Kay (2005 ▶). For the synthesis, see: Valkonen et al. (2007 ▶); Barchin et al. (2002 ▶). For related structures, see: Xu et al. (2006 ▶); Fu et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₆F₃NO₂
M _r = 277.20
Monoclinic,
a = 6.8422 (14) Å
b = 21.082 (4) Å
c = 7.9727 (16) Å
β = 101.98 (3)°
V = 1125.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.972, T _max = 0.983
8049 measured reflections
1980 independent reflections
1603 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.094
S = 1.03
1980 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024177/ng2787sup1.cif

e-66-o1859-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024177/ng2787Isup2.hkl

e-66-o1859-Isup2.hkl^{(97.4KB, hkl)}

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
C4—H4⋯O2ⁱ	0.95	2.55	3.1855 (18)	124
C10—H10⋯F1ⁱⁱ	0.95	2.54	3.3647 (18)	145
C11—H11⋯O1ⁱⁱⁱ	0.95	2.55	3.428 (2)	154

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

Acknowledgments

The work was supported by the Major Research Program of Zhejiang Province (No. 2008 C02007–2) and the Zhejiang Provincial Natural Science Foundation of China (No. Y307128).

supplementary crystallographic information

Comment

The title compound is a key intermediate in the synthesis of organic electro-luminescent materials. The emission of light by organic molecules exposed to an electric field has been wide investigated in both an academic and industrial context. (Han & Kay, 2005).

The molecular structure of the title compound is illustrated in Fig. 1. In the title compound, two rings are nearly planar, but the molecule as a whole is not planar. The dihedral angle between the benzene ring and the phthalimide plane is 60.12 (7) °, which is similar to 59.95 (4) ° found in a related compound N-(2-fluorophenyl)phthalimide (Xu et al. 2006). Weak intermolecular C—H···O and C—H···F hydrogen bonding are present in the crystal structure (Table 1).

Experimental

An acetic acid solution of phthalic anhydride (14.8 g, 100 mmol) and 2,3,4-trifluoroaniline (10.55 ml, 100 mmol) was refluxed overnight, and then filtered. The crude product was recrystallized from ethyl acetate.