Phenyl N-[4-chloro-3-(trifluoro­meth­yl)phen­yl]carbamate

Hai-Tao Tang; Zheng Fang

doi:10.1107/S1600536809004942

. 2009 Feb 18;65(Pt 3):o537. doi: 10.1107/S1600536809004942

Phenyl N-[4-chloro-3-(trifluoromethyl)phenyl]carbamate

Hai-Tao Tang ^a, Zheng Fang ^a,^*

PMCID: PMC2968454 PMID: 21582197

Abstract

In the molecule of the title compound, C₁₄H₉ClF₃NO₂, the aromatic rings are oriented at a dihedral angle of 66.49 (3)°. Intramolecular C—H⋯F and C—H⋯O interactions result in the formation of one planar five- and one non-planar six-membered ring. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains.

Related literature

For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₉ClF₃NO₂
M _r = 315.67
Orthorhombic,
a = 8.5680 (17) Å
b = 11.152 (2) Å
c = 14.232 (3) Å
V = 1359.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 294 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.910, T _max = 0.969
2733 measured reflections
2465 independent reflections
1775 reflections with I > 2σ(I)
R _int = 0.034
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.188
S = 1.00
2465 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack (1983 ▶), 1012 Friedel pairs
Flack parameter: −0.1 (2)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004942/hk2623sup1.cif

e-65-0o537-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004942/hk2623Isup2.hkl

e-65-0o537-Isup2.hkl^{(121.1KB, 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
N—H0A⋯O2ⁱ	0.86	2.10	2.943 (5)	168
C9—H9A⋯O2	0.93	2.44	2.950 (5)	114
C13—H13A⋯F2	0.93	2.34	2.687 (5)	102

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

Some derivatives of benzoic acid are important chemical materials. We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C8-C13) are, of course, planar and the dihedral angle between them is A/B = 66.49 (3)°. The intramolecular C-H···F and C-H···O interactions (Table 1) result in the formations of one planar five- and one nonplanar six-membered rings C (F2/C12-C14/H13A) and D (O2/N/C7-C9/H9A). Ring C is oriented with respect to rings A and B at dihedral angles of 66.33 (3)° and 0.93 (3)°, respectively. So, rings B and C are nearly coplanar.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, phenyl chloroformate (1.0 ml) was added slowly to a cold solution of 4-chloro-3-(trifluoromethyl)benzenamine (1.0 g) and triethylamine (0.8 ml) in methylene chloride (10 ml) at 273 K. The mixture was then warmed and stirred for 1 h at room temperature. Then, it was washed with water (20 ml), dried and concentrated to give the title compound (yield; 1.3 g). Crystals suitable for X-ray analysis were obtained by slow evaporation of an methanol solution.