(E)-O-IsopropylN-(4-nitrophenyl)thiocarbamate

Abstract

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.

Co-crystallization experiments of thiocarbamides with bipyridine-type molecules

“…56,61 This conformation favours the formation of the eight-membered {/H-N-C]S} 2 synthon in the crystal packing and indeed, this synthon is found in 15 of the 17 molecules. [53][54][55][56][57][58][59][60][61][62][63][64][65] In one structure, Oisopropyl N-(2-furoyl)thiocarbamate, intramolecular N-H/S and N-H/O (derived from the 2-furoyl ring) contacts preclude intermolecular association via N-H/S. 66 The final example of a molecule with an E-conformation presents a unique example where there are two independent molecules in the crystallographic asymmetric unit of O-benzyl N-((2-furyl)carbonyl)thiocarbamate.…”

[O-Isopropyl-N-(4-nitrophenyl)thiocarbamato-κS]-(tri-4-tolylphosphine-κP)gold(I)

“…This shows considerable lengthening and shortening in the thiocarbamate anion consistent with significant reorganization of π-electron density in 1 compared to that seen in the original thiocarbamide molecule [12]. The systematic changes in the angles subtended at the quaternary-C1 atom are also consistent with above, with the widest angles subtended by the imine-N1 atom, e.g., S1-C1-O1 is the narrowest angle in 1, at 108.3 4• , but is the widest, at 126.2 2• , in the free molecule [12]. The central CNOS chromophore is strictly planar with the r.m.s.…”

“…In the IR, characteristic bands ascribed to ν(C=N) [1330 (vs)], ν(C-O) [1139 (vs)] and ν(C-S) [1099 (vs)] were observed. No evidence was found for a signal due to N-H in the 1 H-NMR spectrum or of a band due to ν(N-H) in the IR spectrum [12]. In the UV spectrum, the most prominent band at λ abs 240 nm is attributed to the thiolate ligand-centered π→π* transition [13].…”

“…To a first approximation, the gold(I) center is linearly coordinated by thiolate-S1 and phosphane-P1 atoms. The thiolate assignment is readily vindicated by comparing the C1-S1 and C1-N1 bond lengths of 1, i.e., 1.771(5) and 1.260(8) Å, respectively, with the equivalent bonds of recorded for the free ligand, i.e., S=C(O-i-Pr)N(H)C6H4NO2-4, of 1.678 (3) and 1.352 (3) Å, respectively [12]. This shows considerable lengthening and shortening in the thiocarbamate anion consistent with significant reorganization of π-electron density in 1 compared to that seen in the original thiocarbamide molecule [12].…”

“…The thiolate assignment is readily vindicated by comparing the C1-S1 and C1-N1 bond lengths of 1, i.e., 1.771(5) and 1.260(8) Å, respectively, with the equivalent bonds of recorded for the free ligand, i.e., S=C(O-i-Pr)N(H)C6H4NO2-4, of 1.678 (3) and 1.352 (3) Å, respectively [12]. This shows considerable lengthening and shortening in the thiocarbamate anion consistent with significant reorganization of π-electron density in 1 compared to that seen in the original thiocarbamide molecule [12]. The systematic changes in the angles subtended at the quaternary-C1 atom are also consistent with above, with the widest angles subtended by the imine-N1 atom, e.g., S1-C1-O1 is the narrowest angle in 1, at 108.3(4)°, but is the widest, at 126.2(2)°, in the free molecule [12].…”