(E)-O-Isopropyl N-(4-nitrophenyl)thiocarbamate

The configuration of the thione–aryl C—N single bond in the title molecule, C10H12N2O3S, is E. Centrosymmetrically related molecules are connected into a dimer via an eight-membered thioamide {⋯H—N—C=S}2 synthon and molecules are consolidated into the crystal structure via C—H⋯O interactions.

The configuration of the thione-aryl C-N single bond in the title molecule, C 10 H 12 N 2 O 3 S, is E. Centrosymmetrically related molecules are connected into a dimer via an eightmembered thioamide {Á Á ÁH-N-C S} 2 synthon and molecules are consolidated into the crystal structure via C-HÁ Á ÁO interactions.
The MBRS RISE program (GM 60655) is thanked for the support of CAE. We thank CNPq and FAPESP (Brazil) and UTSA for support to allow JZ-S to spend a sabbatical at UTSA.

Comment
The title thiocarbamate (I), Fig. 1, was investigated as a part of an on-going evaluation of the structural features of these molecules (Ho et al., 2005;Kuan et al., 2007) along with their phosphinegold(I) complexes (Ho et al., 2006;Ho & Tiekink, 2007). While the central portion of the molecule is planar, small twists are evident in the outer extremities as seen in the N1/C1/O1/H8 and C1/N1/C2/C3 torsion angles of 33 and −20.0 (5)°, respectively. Geometric parameters resemble those found in related systems (Ho et al., 2005;Kuan et al., 2007). The key synthon in the crystal structure is the eight-membered thioamide {···H-N-C=S} 2 synthon, Table 1, as found in most thiocarbamate structures (Kuan et al., 2007). The dimers thus formed stack into layers along the c axis with the alkyl groups projecting on either side to from aliphatic layers.
Interactions of the type C-H···O, involving each of the nitro-O atoms, are formed within and between layers, Table 1.

Experimental
Compound (I) was prepared by refluxing 4-nitrophenylisothiocyanate (Aldrich) with 2-propanol using standard methods (Ho et al., 2005). The yellow precipitate, which was obtained upon concentration of the reaction solution, was dissolved in diethyl ether and layered with hexane in a 1:1 ratio. Yellow crystals were isolated by slow evaporation; m. p. 465 − 469 K. IR

Refinement
All H atoms were included in the riding-model approximation with C-H = 0.95 to 1.00 Å and N-H = 0.88 Å, and with U iso (H) = 1.5U eq (methyl-C) or 1.2U eq (N and remaining-C).   as large as those based on F, and R-factors based on ALL data will be even larger.