4-Nitro­phenyl N-(2-isopropyl­thia­zol-4-ylmeth­yl)-N-methyl­carbamate

Hao Xu; Peng Wang; Wen-Long Huang

doi:10.1107/S1600536807063532

. 2007 Dec 6;64(Pt 1):o149. doi: 10.1107/S1600536807063532

4-Nitrophenyl N-(2-isopropylthiazol-4-ylmethyl)-N-methylcarbamate

Hao Xu ^a, Peng Wang ^b, Wen-Long Huang ^b,^*

PMCID: PMC2915217 PMID: 21200713

Abstract

In the title compound, C₁₅H₁₇N₃O₄S, the benzene and thiazole rings are oriented at a dihedral angle of 74.10 (3)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds are found.

Related literature

For related literature, see: Allen et al. (1987 ▶); Ishikawa et al. (1998 ▶); Riden & Hopkins (1961 ▶).

Experimental

Crystal data

C₁₅H₁₇N₃O₄S
M _r = 335.38
Orthorhombic,
a = 12.250 (3) Å
b = 10.876 (2) Å
c = 24.845 (5) Å
V = 3310.1 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) 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 = 0.937, T _max = 0.979
3281 measured reflections
3241 independent reflections
1335 reflections with I > 2σ(I)
R _int = 0.072
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.086
wR(F ²) = 0.217
S = 1.04
3241 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.39 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, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Siemens,1996 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063532/bq2046sup1.cif

e-64-0o149-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063532/bq2046Isup2.hkl

e-64-0o149-Isup2.hkl^{(159.1KB, 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
C2—H2C⋯O4ⁱ	0.96	2.58	3.493 (7)	159

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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

The title compound, C₁₅H₁₇N₃O₄S, is one of aromatic carbamates which are an important class of esters compounds and have widespread applications from pharmaceuticals (Ishikawa et al., 1998) to agronomy (Riden & Hopkins, 1961). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (C4/N1/C5/C6/S) and B (C10—C15) are almost planar and they are oriented at a dihedral angle of 74.1°.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules (Fig.2), in which they seem to be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, (I), a solution of N-methyl-N-((2-isopropyl-4-thiazoyl)methyl)amine (3.7 g, 21.7 mmol) and excess N-methyl morpholine in methylene chloride (70 ml) was cooled to 273 K, and treated with 4-nitophenyl chloroformate (6.0 g, 30 mmol). After being stirred for 6 h, the reaction mixture was diluted with CHCl₃, washed successively with 1 N HCl, saturated aqueous NaHCO₃, and saturated bine, dried over NaSO₄, and concentrated in vacuo. The residue was purified by silica gel chromatography with 100% CHCl₃ to provide the title compound, (I) (yield: 6.5 g, 87%). Crystals of (I) suitable for x-ray analysis were obtained by slow evaporation of an ethanol solution.