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Licensed Unlicensed Requires Authentication Published by De Gruyter (O) July 28, 2010

Crystal and molecular structures of P,P-dicyclohexyl-N-methyl-phosphinylthioformamide, P,P-dicyclohexyl-N-phenyl-phosphinylthioformamide, P,P-dicyclohexyl-N-methyl-thiophosphinylthioformamide, and P,P-dicyclohexyl-N-phenyl-thiophosphinylthioformamide

Abstract

The crystal structures of the title compounds P,P-dicyclohexyl-N-methyl-phosphinylthioformamide, [cHex2P(O)C(S)N(H)Me], C14H26ONPS, P,P-dicyclohexyl-N-phenylphosphinylthioformamide, [cHex2P(O)C(S)N(H)Ph], C19H28ONPS, P,P-dicyclohexyl-N-methylthiophosphinylthioformamide, [cHex2P(S)C(S)N(H)Me], C14H26NPS2, and P,P-dicyclohexyl-N-phenyl-thiophosphinylthioformamide, [cHex2P(S)C(S)N(H)Ph], C19H28NPS2, have been determined at room temperature. The green crystals of [cHex2P(O)C(S)N(H)Me] are monoclinic, space group C2/c, with unit cell dimensions a = 10.247(2) Å, b = 16.025(4) Å, c = 19.358(4) Å, β = 97.75(2)°, Z = 8 and Dx = 1.212 Mg m−3. Crystals of [cHex2P(O)C(S)N(H)Ph] are also monoclinic, space group C2/c, with unit cell dimensions a = 14.856(4) Å, b = 11.666(4) Å, c = 22.039(3) Å, β = 95.59(1)°, Z = 8 and Dx = 1.221 Mg m−3. The colorless crystals of [cHex2P(S)C(S)N(H)Me] are orthorhombic, crystallizing in the Pnma space group with dimensions a = 10.2600(9) Å, b = 15.447(2) Å, c = 10.141(3) Å, Z = 4 and Dx = 1.254 Mg m−3. Yellow crystals of [cHex2P(S)C(S)N(H)Ph] are triclinic, space group P[unk], with dimensions a = 9.766(2) Å, b = 11.111(2) Å, c = 9.388(2) Å α = 100.54(2)°, β = 104.66(1)° and γ = 83.86(1)°, Z = 2 and Dx = 1.249 Mg m−3. The structures were solved by directmethods and each refined by a full-matrix least-squares procedure to final R = 0.036 (0.046; 0.040; and 0.038) using 1383 (1257; 1362; and 2758) reflections for each of the above [cHex2P(Y)C(S)N(H)R] (where Y = O or S and R = Me or Ph) compounds, respectively. The conformation about the C–N bond in each of [cHex2P(Y)C(S)N(H)R] is Z. Important parameters for Y = O, R = Me: P = O 1.480(2), P–C 1.814(4), C = S 1.630(3) and C–N 1.306(4) Å; Y = O, R = Ph: P = O 1.479(4), P–C 1.817(5), C = S 1.618(5) and C–N 1.327(6) Å; Y = S, R = Me: P = S 1.942(1), P–C 1.823(4), C = S 1.644(4) and C–N 1.290(5) Å; and Y = S, R = Ph: P = S 1.9495(9), P–C 1.846(3), C = S 1.624(2) and C–N 1.317(3) Å. Symmetry related molecules of [cHex2P(O)C(S)N(H)R] associate in the lattice via hydrogen bonding contacts. The P–C(1) bond distances in the [cHex2P(Y)C(S)N(H)R] compounds are shown to be significantly shorter than those found in the related [Ph2P(Y)C(S)N(H)R] compounds.

Published Online: 2010-7-28
Published in Print: 1994-11-1

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