Phenyl N-(1,3-thia­zol-2-yl)carbamate

Jian-Guo Tang; Yong-Zhong Wu; Sheng Bi; Guo-Hua Zhang; Cheng Guo

doi:10.1107/S1600536809020236

. 2009 Jun 6;65(Pt 7):o1478. doi: 10.1107/S1600536809020236

Phenyl N-(1,3-thiazol-2-yl)carbamate

Jian-Guo Tang ^a, Yong-Zhong Wu ^b, Sheng Bi ^a, Guo-Hua Zhang ^a, Cheng Guo ^a,^*

PMCID: PMC2969196 PMID: 21582780

Abstract

In the title compound, C₁₀H₈N₂O₂S, the planes of the aromatic rings are oriented at a dihedral angle of 66.69 (3)°. In the crystal structure, intermolecular N—H⋯N and C—H⋯O interactions link the molecules into a two-dimensional network, forming R ₂ ²(8) ring motifs. π–π contacts between the thiazole rings [centroid–centroid distance = 3.535 (1) Å] may further stabilize the structure. A weak C—H⋯π interaction is also found.

Related literature

For a related structure, see: Araujo et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₀H₈N₂O₂S
M _r = 220.24
Monoclinic,
a = 5.6430 (11) Å
b = 7.3910 (15) Å
c = 25.134 (5) Å
β = 91.21 (3)°
V = 1048.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.29 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 = 0.918, T _max = 0.972
2084 measured reflections
1880 independent reflections
1346 reflections with I > 2σ(I)
R _int = 0.027
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.160
S = 1.00
1880 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020236/hk2701sup1.cif

e-65-o1478-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020236/hk2701Isup2.hkl

e-65-o1478-Isup2.hkl^{(92.6KB, 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
N1—H1A⋯N2ⁱ	0.86	2.01	2.864 (4)	171
C3—H3A⋯O2ⁱⁱ	0.93	2.46	3.335 (4)	156
C5—H5A⋯Cg2ⁱⁱⁱ	0.93	2.98	3.736 (3)	139

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg2 is the centroid of the S/N2/C8–C10 ring.

Acknowledgments

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

supplementary crystallographic information

Comment

Some derivatives of phenol 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 (S/N2/C8-C10) are, of course, planar and they are oriented at a dihedral angle of 66.69 (3)°. Atoms O1, O2, N1, C4, C7, H1A, H9A and H10B are 0.118 (3), -0.063 (3), 0.028 (3), 0.172 (3), 0.023 (3), 0.051 (3), 0.002 (3) and -0.002 (3) Å away from the plane of ring B, respectively.

In the crystal structure, intermolecular N-H···N and C-H···O interactions (Table 1) link the molecules into a two-dimensional network forming R₂²(8) ring motifs (Bernstein et al., 1995) (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the thiazole rings, Cg2—Cg2ⁱ, [symmetry code: (i) 1 - x, -y, -z, where Cg2 is centroid of the ring B (S/N2/C8-C10)] may further stabilize the structure, with centroid-centroid distance of 3.535 (1) Å. There also exists a weak C—H···π interaction (Table 1).

Experimental

For the preparation of the title compound, phenyl chloroformate (1.0 ml) was added slowly to a cold solution of thiazol-2-amine (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) (Araujo et al., 2006). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.