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The crystal structures of the title compounds  P , P -dicyclohexyl- N -methyl-phosphinylthioformamide, [ c Hex 2 P(O)C(S)N(H)Me], C 14 H 26 ONPS,  P , P -dicyclohexyl- N -phenylphosphinylthioformamide, [ c Hex 2 P(O)C(S)N(H)Ph], C 19 H 28 ONPS,  P , P -dicyclohexyl- N -methylthiophosphinylthioformamide, [ c Hex 2 P(S)C(S)N(H)Me], C 14 H 26 NPS 2 , and  P , P -dicyclohexyl- N -phenyl-thiophosphinylthioformamide, [ c Hex 2 P(S)C(S)N(H)Ph], C 19 H 28 NPS 2 , have been determined at room temperature. The green crystals of [ c Hex 2 P(O)C(S)N(H)Me] are monoclinic, space group  C 2/ 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  D  x  = 1.212 Mg m −3 . Crystals of [ c Hex 2 P(O)C(S)N(H)Ph] are also monoclinic, space group  C 2/ 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  D  x  = 1.221 Mg m −3 . The colorless crystals of [ c Hex 2 P(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  D  x  = 1.254 Mg m −3 . Yellow crystals of [ c Hex 2 P(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  D  x  = 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 [ c Hex 2 P(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 [ c Hex 2 P(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 [ c Hex 2 P(O)C(S)N(H)R] associate in the lattice via hydrogen bonding contacts. The P–C(1) bond distances in the [ c Hex 2 P(Y)C(S)N(H)R] compounds are shown to be significantly shorter than those found in the related [Ph 2 P(Y)C(S)N(H)R] compounds.

zeitschrift für kristallographie - crystalline materials

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