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The molecular structure of the title compound, Cy2P(=S)­C(=S)N(H)Ph (Cy is cyclo­hexyl) or C19H28NPS2, is virtually identical to that found in the previously reported triclinic polymorph. Thus, the conformation about the C-N bond is Z and the dimensions defining the central P(=S)C(=S)NC group in both forms are experimentally equivalent.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100410X/ci6013sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100410X/ci6013Isup2.hkl
Contains datablock I

CCDC reference: 162815

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.028
  • Data-to-parameter ratio = 15.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry




Comment top

Compounds of the general formula R2P(Y)C(S)N(H)R' (where R, R' = alkyl or aryl, and Y = 0, O, S or Se) are known to adopt of a variety of coordination modes in both their neutral and deprotonated forms (Siasios & Tiekink, 1996a,b; Horn et al., 2000). Consequently, systematic structural studies have been conducted on these ligands (Cowan et al., 1984; Siasios & Tiekink, 1994, 1995a,b). The structure of the title compound, Cy2P(S)C(S)N(H)Ph, (I), represents a second polymorph, a triclinic form having been determined previously (Siasios & Tiekink, 1994).

The key geometric parameters defining the P(S)C(S)NC chromphore [e.g. P1—S2 1.9655 (8) Å, C1—S1 1.639 (2) Å, P1—C1 1.866 (2) Å, N1—C1 1.334 (3) Å and S2—P1—C1—S1 - 166.1 (1)°] are equal within experimental error to those in the triclinic form (Siasios & Tiekink, 1994). The major difference between the polymorphs is found in the relative orientations of the cyclohexyl rings. Thus, whilst the P(S)C(S)N(H)Ph portions of the molecules are essentially superimposable in the two forms, the cyclohexyl groups are not. Referring to Fig. 1, it can be seen that the methine H atom bound to C8 is directed towards the same side of the molecule as S2, and the C14 H atom is directed towards the same side as the S1 atom. Opposite orientations are observed in the triclinic form (Siasios & Tiekink, 1994).

Experimental top

Crystals of the title compound (Ojima et al., 1969) were isolated by slow evaporation of a CH2Cl2 solution at room temperature (m. p. 382–385 K).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1992); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. A view of Cy2P(S)C(S)N(H)Ph in the monoclinic polymorph showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50° probability level (Johnson, 1976).
(I) top
Crystal data top
C19H28NPS2F(000) = 784
Mr = 365.53Dx = 1.210 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
a = 10.074 (1) ÅCell parameters from 25 reflections
b = 18.139 (2) Åθ = 11.0–12.2°
c = 11.3858 (9) ŵ = 0.35 mm1
β = 105.426 (8)°T = 293 K
V = 2005.6 (3) Å3Prismatic, yellow
Z = 40.25 × 0.20 × 0.15 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.025
Radiation source: Rigaku rotating anodeθmax = 30.1°, θmin = 2.7°
Graphite monochromatorh = 014
ω–2θ scansk = 025
6358 measured reflectionsl = 1615
6054 independent reflections3 standard reflections every 150 reflections
3143 reflections with I > 2σ(I) intensity decay: 0.6%
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.028 w = 1/[σ2(Fo) + 0.004|Fo|2]
S = 1.69(Δ/σ)max < 0.001
3143 reflectionsΔρmax = 0.21 e Å3
208 parametersΔρmin = 0.16 e Å3
Crystal data top
C19H28NPS2V = 2005.6 (3) Å3
Mr = 365.53Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.074 (1) ŵ = 0.35 mm1
b = 18.139 (2) ÅT = 293 K
c = 11.3858 (9) Å0.25 × 0.20 × 0.15 mm
β = 105.426 (8)°
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.025
6358 measured reflections3 standard reflections every 150 reflections
6054 independent reflections intensity decay: 0.6%
3143 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.028H-atom parameters constrained
S = 1.69Δρmax = 0.21 e Å3
3143 reflectionsΔρmin = 0.16 e Å3
208 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.39714 (8)0.20810 (4)0.11082 (7)0.0586 (2)
S20.28158 (7)0.06445 (4)0.40850 (6)0.0547 (2)
P10.39855 (6)0.09220 (3)0.30227 (6)0.0385 (2)
N10.2560 (2)0.21695 (10)0.2808 (2)0.0435 (6)
C10.3403 (2)0.1822 (1)0.2265 (2)0.0379 (6)
C20.1907 (2)0.2870 (1)0.2620 (2)0.0410 (7)
C30.2116 (2)0.3395 (1)0.1811 (2)0.0480 (8)
C40.1426 (3)0.4062 (1)0.1726 (2)0.0581 (9)
C50.0542 (3)0.4210 (1)0.2427 (3)0.0632 (9)
C60.0348 (3)0.3688 (2)0.3238 (3)0.067 (1)
C70.1021 (3)0.3019 (1)0.3345 (2)0.0550 (9)
C80.5784 (2)0.1064 (1)0.3875 (2)0.0412 (7)
C90.5899 (3)0.1720 (1)0.4746 (2)0.0519 (8)
C100.7367 (3)0.1806 (1)0.5543 (2)0.0645 (9)
C110.8383 (3)0.1882 (1)0.4780 (3)0.0662 (9)
C120.8283 (3)0.1227 (2)0.3930 (3)0.069 (1)
C130.6824 (3)0.1133 (1)0.3107 (2)0.0572 (9)
C140.3931 (2)0.0270 (1)0.1799 (2)0.0407 (7)
C150.2473 (3)0.0170 (1)0.0981 (2)0.0551 (8)
C160.2462 (3)0.0380 (2)0.0042 (2)0.0664 (10)
C170.3101 (3)0.1115 (1)0.0461 (3)0.0658 (10)
C180.4526 (3)0.1022 (1)0.1302 (3)0.0620 (9)
C190.4538 (3)0.0476 (1)0.2319 (2)0.0525 (8)
H10.23610.19000.34350.0521*
H20.27250.33010.13190.0576*
H30.15680.44250.11700.0697*
H40.00700.46680.23530.0758*
H50.02570.37880.37310.0800*
H60.08810.26610.39100.0660*
H70.60520.06310.43830.0495*
H80.56310.21660.42740.0622*
H90.52870.16410.52640.0622*
H100.74190.22430.60440.0774*
H110.76080.13760.60610.0774*
H120.81830.23300.43000.0795*
H130.93090.19080.53150.0795*
H140.89110.13020.34260.0825*
H150.85420.07840.44140.0825*
H160.67850.06910.26190.0686*
H170.65890.15580.25760.0686*
H180.44990.04640.13030.0488*
H190.18830.00120.14660.0661*
H200.21290.06420.06260.0661*
H210.15170.04630.05080.0797*
H220.29810.01750.05700.0797*
H230.25170.13470.09080.0790*
H240.31570.14280.02140.0790*
H250.48500.14960.16600.0745*
H260.51370.08440.08340.0745*
H270.54790.04030.28010.0630*
H280.39940.06730.28330.0630*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0833 (5)0.0449 (4)0.0609 (4)0.0122 (4)0.0422 (4)0.0146 (3)
S20.0665 (5)0.0497 (4)0.0583 (4)0.0028 (4)0.0345 (4)0.0140 (3)
P10.0460 (4)0.0315 (3)0.0410 (3)0.0029 (3)0.0170 (3)0.0051 (3)
N10.049 (1)0.041 (1)0.047 (1)0.0076 (10)0.0221 (10)0.0105 (9)
C10.041 (1)0.033 (1)0.041 (1)0.003 (1)0.013 (1)0.004 (1)
C20.036 (1)0.038 (1)0.048 (1)0.005 (1)0.008 (1)0.002 (1)
C30.047 (2)0.040 (1)0.060 (2)0.007 (1)0.020 (1)0.003 (1)
C40.060 (2)0.038 (1)0.075 (2)0.006 (1)0.015 (2)0.005 (1)
C50.058 (2)0.048 (2)0.080 (2)0.015 (1)0.012 (2)0.008 (2)
C60.055 (2)0.072 (2)0.077 (2)0.020 (2)0.025 (2)0.008 (2)
C70.052 (2)0.057 (2)0.062 (2)0.009 (1)0.026 (1)0.007 (1)
C80.045 (1)0.032 (1)0.047 (1)0.006 (1)0.012 (1)0.004 (1)
C90.059 (2)0.042 (2)0.053 (2)0.005 (1)0.012 (1)0.006 (1)
C100.069 (2)0.051 (2)0.065 (2)0.001 (2)0.003 (2)0.007 (1)
C110.054 (2)0.046 (2)0.090 (2)0.002 (1)0.003 (2)0.001 (2)
C120.048 (2)0.063 (2)0.096 (2)0.000 (1)0.022 (2)0.009 (2)
C130.050 (2)0.059 (2)0.067 (2)0.000 (1)0.023 (1)0.008 (1)
C140.049 (2)0.033 (1)0.042 (1)0.001 (1)0.017 (1)0.001 (1)
C150.058 (2)0.045 (2)0.059 (2)0.000 (1)0.010 (1)0.001 (1)
C160.073 (2)0.056 (2)0.062 (2)0.007 (2)0.006 (2)0.009 (1)
C170.082 (2)0.044 (2)0.073 (2)0.013 (2)0.025 (2)0.014 (1)
C180.075 (2)0.038 (1)0.075 (2)0.001 (1)0.025 (2)0.008 (1)
C190.060 (2)0.037 (1)0.061 (2)0.005 (1)0.018 (1)0.000 (1)
Geometric parameters (Å, º) top
S1—C11.639 (2)C8—C91.534 (3)
S2—P11.9655 (8)C8—C131.538 (3)
P1—C11.866 (2)C9—C101.524 (3)
P1—C81.832 (2)C10—C111.514 (4)
P1—C141.817 (2)C11—C121.518 (4)
N1—C11.334 (3)C12—C131.528 (3)
N1—C21.420 (3)C14—C151.527 (3)
C2—C31.380 (3)C14—C191.537 (3)
C2—C71.393 (3)C15—C161.532 (3)
C3—C41.387 (3)C16—C171.524 (4)
C4—C51.371 (3)C17—C181.509 (4)
C5—C61.372 (4)C18—C191.522 (3)
C6—C71.380 (3)
S1···C9i3.536 (2)
S2—P1—C1110.00 (7)C12—C11—H12109.2
S2—P1—C8112.35 (8)C12—C11—H13109.2
S2—P1—C14113.86 (8)H12—C11—H13109.5
C1—P1—C8105.51 (10)C11—C12—C13111.6 (2)
C1—P1—C14105.85 (10)C11—C12—H14108.9
C8—P1—C14108.7 (1)C11—C12—H15108.9
C1—N1—C2132.8 (2)C13—C12—H14108.9
C1—N1—H1113.6C13—C12—H15108.9
C2—N1—H1113.6H14—C12—H15109.5
S1—C1—P1119.2 (1)C8—C13—C12110.5 (2)
S1—C1—N1129.6 (2)C8—C13—H16109.2
P1—C1—N1111.1 (2)C8—C13—H17109.2
N1—C2—C3124.8 (2)C12—C13—H16109.2
N1—C2—C7115.4 (2)C12—C13—H17109.2
C3—C2—C7119.8 (2)H16—C13—H17109.5
C2—C3—C4119.1 (2)P1—C14—C15111.9 (2)
C2—C3—H2120.4P1—C14—C19110.5 (2)
C4—C3—H2120.4P1—C14—H18108.0
C3—C4—C5121.4 (2)C15—C14—C19110.5 (2)
C3—C4—H3119.3C15—C14—H18108.0
C5—C4—H3119.3C19—C14—H18108.0
C4—C5—C6119.2 (2)C14—C15—C16110.6 (2)
C4—C5—H4120.4C14—C15—H19109.2
C6—C5—H4120.4C14—C15—H20109.2
C5—C6—C7120.8 (2)C16—C15—H19109.2
C5—C6—H5119.6C16—C15—H20109.2
C7—C6—H5119.6H19—C15—H20109.5
C2—C7—C6119.7 (2)C15—C16—C17111.6 (2)
C2—C7—H6120.2C15—C16—H21109.0
C6—C7—H6120.2C15—C16—H22109.0
P1—C8—C9110.2 (2)C17—C16—H21108.9
P1—C8—C13116.0 (2)C17—C16—H22108.9
P1—C8—H7106.3H21—C16—H22109.5
C9—C8—C13111.0 (2)C16—C17—C18112.1 (2)
C9—C8—H7106.3C16—C17—H23108.8
C13—C8—H7106.3C16—C17—H24108.8
C8—C9—C10111.0 (2)C18—C17—H23108.8
C8—C9—H8109.1C18—C17—H24108.8
C8—C9—H9109.1H23—C17—H24109.5
C10—C9—H8109.1C17—C18—C19111.7 (2)
C10—C9—H9109.1C17—C18—H25108.9
H8—C9—H9109.5C17—C18—H26108.9
C9—C10—C11111.4 (2)C19—C18—H25108.9
C9—C10—H10109.0C19—C18—H26108.9
C9—C10—H11109.0H25—C18—H26109.5
C11—C10—H10109.0C14—C19—C18111.0 (2)
C11—C10—H11109.0C14—C19—H27109.1
H10—C10—H11109.5C14—C19—H28109.1
C10—C11—C12110.7 (2)C18—C19—H27109.1
C10—C11—H12109.2C18—C19—H28109.1
C10—C11—H13109.2H27—C19—H28109.5
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC19H28NPS2
Mr365.53
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.074 (1), 18.139 (2), 11.3858 (9)
β (°) 105.426 (8)
V3)2005.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6358, 6054, 3143
Rint0.025
(sin θ/λ)max1)0.706
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.028, 1.69
No. of reflections3143
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.16

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1992), SIR92 (Altomare et al., 1994), TEXSAN, ORTEPII (Johnson, 1976).

 

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