organic compounds
N,N-Dibenzyl-O,O′-dimethyl thiophosphate
aFaculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, bDepartment of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran, cDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and dDepartment of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, Brno CZ-61137, Czech Republic
*Correspondence e-mail: a.raissi_shabari@yahoo.com
The P atom in the title compound, C16H20NO2PS, is bonded in a distorted tetrahedral P(S)(O)2N environment with the bond angles at the P atom in the range 99.37 (7) to 115.68 (5)°. The angles at the amido N atom (with bond-angle sum of 357.8°) confirm its sp2 character. The C—O—P bond angles are 119.78 (11) and 119.39 (12)°.
Related literature
For a related phosphoramidothioate structure, see: Sabbaghi et al. (2012). For structures with a P—N(CH2C6H5)2 fragment, see: Pourayoubi et al. (2012).
Experimental
Crystal data
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004).
Supporting information
10.1107/S1600536812041220/lh5538sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041220/lh5538Isup2.hkl
To a solution of dimethyl chlorothiophosphate, [CH3O]2P(S)Cl, (1.7 mmol) in dry CH3CN (30 ml), a solution of dibenzylamine (3.4 mmol) in the same solvent (5 ml) was added at ice bath temperature. After 4 h stirring, the solvent was removed and the product was washed with distilled water and recrystallized from methanol at room temperature. The single crystals, suitable for X-ray analysis were obtained from this solution after a few days at room temperature.
All carbon bound H atoms were placed in calculated positions and were refined as riding with their Uiso set to either 1.2Ueq or 1.5Ueq (methyl) of the respective carrier atoms; in addition, the methyl H atoms were allowed to rotate about the C—C bond.
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004).Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level and H atoms are drawn as small spheres of arbitrary radii. |
C16H20NO2PS | F(000) = 680 |
Mr = 321.36 | Dx = 1.345 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2953 reflections |
a = 6.8377 (3) Å | θ = 3.1–27.6° |
b = 8.1115 (4) Å | µ = 0.31 mm−1 |
c = 28.6187 (16) Å | T = 120 K |
V = 1587.31 (14) Å3 | Prism, colourless |
Z = 4 | 0.75 × 0.55 × 0.25 mm |
Oxford Diffraction Xcalibur Sapphire2 diffractometer | 3010 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2747 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Detector resolution: 8.4353 pixels mm-1 | θmax = 27.7°, θmin = 3.1° |
ω scan | h = −4→8 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | k = −7→10 |
Tmin = 0.802, Tmax = 0.927 | l = −18→37 |
4397 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0379P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3010 reflections | Δρmax = 0.25 e Å−3 |
192 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 982 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.04 (7) |
C16H20NO2PS | V = 1587.31 (14) Å3 |
Mr = 321.36 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.8377 (3) Å | µ = 0.31 mm−1 |
b = 8.1115 (4) Å | T = 120 K |
c = 28.6187 (16) Å | 0.75 × 0.55 × 0.25 mm |
Oxford Diffraction Xcalibur Sapphire2 diffractometer | 3010 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2747 reflections with I > 2σ(I) |
Tmin = 0.802, Tmax = 0.927 | Rint = 0.014 |
4397 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.064 | Δρmax = 0.25 e Å−3 |
S = 1.03 | Δρmin = −0.31 e Å−3 |
3010 reflections | Absolute structure: Flack (1983), 982 Friedel pairs |
192 parameters | Absolute structure parameter: −0.04 (7) |
0 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.1193 (3) | 0.0377 (2) | 0.26315 (7) | 0.0250 (4) | |
H1A | −0.1339 | 0.0939 | 0.2330 | 0.037* | |
H1B | −0.2488 | 0.0089 | 0.2754 | 0.037* | |
H1C | −0.0420 | −0.0629 | 0.2589 | 0.037* | |
C2 | −0.2073 (3) | −0.0532 (2) | 0.40718 (7) | 0.0259 (4) | |
H2A | −0.3466 | −0.0609 | 0.4149 | 0.039* | |
H2B | −0.1372 | −0.0006 | 0.4331 | 0.039* | |
H2C | −0.1545 | −0.1640 | 0.4020 | 0.039* | |
C3 | −0.0215 (2) | 0.3937 (2) | 0.37593 (6) | 0.0155 (4) | |
H3A | −0.1422 | 0.3714 | 0.3579 | 0.019* | |
H3B | 0.0473 | 0.4869 | 0.3608 | 0.019* | |
C4 | 0.3118 (2) | 0.2750 (2) | 0.38807 (6) | 0.0150 (4) | |
H4A | 0.3780 | 0.1672 | 0.3918 | 0.018* | |
H4B | 0.3144 | 0.3312 | 0.4188 | 0.018* | |
C5 | −0.0757 (2) | 0.4412 (2) | 0.42528 (6) | 0.0159 (4) | |
C6 | 0.0174 (3) | 0.5705 (2) | 0.44800 (6) | 0.0200 (4) | |
H6 | 0.1180 | 0.6297 | 0.4324 | 0.024* | |
C7 | −0.0350 (3) | 0.6145 (2) | 0.49342 (7) | 0.0251 (4) | |
H7 | 0.0297 | 0.7031 | 0.5086 | 0.030* | |
C8 | −0.1815 (3) | 0.5286 (2) | 0.51624 (7) | 0.0245 (4) | |
H8 | −0.2167 | 0.5575 | 0.5473 | 0.029* | |
C9 | −0.2761 (3) | 0.4010 (2) | 0.49388 (7) | 0.0245 (4) | |
H9 | −0.3773 | 0.3426 | 0.5095 | 0.029* | |
C10 | −0.2240 (3) | 0.3574 (2) | 0.44868 (6) | 0.0200 (4) | |
H10 | −0.2903 | 0.2695 | 0.4335 | 0.024* | |
C11 | 0.4258 (2) | 0.3774 (2) | 0.35330 (6) | 0.0157 (4) | |
C12 | 0.4820 (3) | 0.3088 (2) | 0.31086 (6) | 0.0189 (4) | |
H12 | 0.4468 | 0.1982 | 0.3039 | 0.023* | |
C13 | 0.5879 (3) | 0.3985 (2) | 0.27863 (6) | 0.0215 (4) | |
H13 | 0.6242 | 0.3500 | 0.2497 | 0.026* | |
C14 | 0.6414 (3) | 0.5599 (2) | 0.28866 (6) | 0.0211 (4) | |
H14 | 0.7158 | 0.6217 | 0.2668 | 0.025* | |
C15 | 0.5860 (3) | 0.6299 (2) | 0.33044 (7) | 0.0223 (4) | |
H15 | 0.6212 | 0.7406 | 0.3372 | 0.027* | |
C16 | 0.4789 (3) | 0.5395 (2) | 0.36273 (7) | 0.0191 (4) | |
H16 | 0.4416 | 0.5887 | 0.3915 | 0.023* | |
N1 | 0.1058 (2) | 0.24562 (18) | 0.37470 (5) | 0.0143 (3) | |
O1 | −0.02041 (18) | 0.14624 (14) | 0.29598 (4) | 0.0176 (3) | |
O2 | −0.18301 (17) | 0.04395 (15) | 0.36533 (4) | 0.0186 (3) | |
P1 | 0.03212 (6) | 0.08173 (5) | 0.346520 (16) | 0.01436 (11) | |
S2 | 0.20827 (7) | −0.10397 (5) | 0.348938 (16) | 0.02011 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0280 (10) | 0.0296 (10) | 0.0173 (10) | −0.0001 (9) | −0.0063 (9) | −0.0056 (8) |
C2 | 0.0274 (10) | 0.0254 (10) | 0.0248 (10) | −0.0004 (9) | 0.0074 (9) | 0.0080 (8) |
C3 | 0.0169 (8) | 0.0151 (8) | 0.0145 (9) | 0.0038 (8) | −0.0013 (7) | 0.0016 (7) |
C4 | 0.0134 (8) | 0.0167 (8) | 0.0148 (9) | 0.0008 (7) | −0.0029 (8) | −0.0013 (7) |
C5 | 0.0153 (8) | 0.0151 (9) | 0.0174 (9) | 0.0069 (7) | −0.0009 (7) | 0.0013 (7) |
C6 | 0.0210 (9) | 0.0195 (9) | 0.0195 (10) | 0.0003 (8) | 0.0023 (8) | 0.0019 (8) |
C7 | 0.0310 (10) | 0.0208 (9) | 0.0237 (10) | 0.0016 (9) | −0.0035 (9) | −0.0038 (8) |
C8 | 0.0299 (10) | 0.0295 (10) | 0.0141 (9) | 0.0086 (9) | 0.0025 (9) | −0.0002 (8) |
C9 | 0.0211 (9) | 0.0289 (10) | 0.0235 (10) | 0.0049 (9) | 0.0059 (8) | 0.0087 (9) |
C10 | 0.0167 (8) | 0.0195 (9) | 0.0239 (10) | 0.0015 (7) | −0.0025 (8) | 0.0012 (8) |
C11 | 0.0107 (7) | 0.0207 (9) | 0.0158 (9) | 0.0037 (7) | −0.0026 (7) | 0.0025 (8) |
C12 | 0.0164 (8) | 0.0226 (9) | 0.0177 (10) | 0.0013 (8) | −0.0039 (8) | −0.0017 (7) |
C13 | 0.0179 (8) | 0.0323 (10) | 0.0142 (9) | 0.0038 (9) | −0.0017 (7) | 0.0013 (9) |
C14 | 0.0145 (8) | 0.0267 (10) | 0.0221 (10) | 0.0019 (8) | −0.0001 (8) | 0.0115 (8) |
C15 | 0.0187 (9) | 0.0163 (9) | 0.0320 (11) | 0.0024 (8) | −0.0015 (8) | 0.0057 (8) |
C16 | 0.0165 (8) | 0.0204 (9) | 0.0204 (9) | 0.0048 (8) | 0.0000 (8) | −0.0005 (8) |
N1 | 0.0125 (6) | 0.0175 (7) | 0.0130 (8) | 0.0033 (6) | −0.0023 (6) | −0.0018 (6) |
O1 | 0.0211 (6) | 0.0173 (6) | 0.0143 (6) | 0.0001 (5) | −0.0030 (6) | −0.0005 (5) |
O2 | 0.0157 (6) | 0.0207 (6) | 0.0194 (6) | −0.0011 (5) | 0.0011 (5) | 0.0035 (5) |
P1 | 0.01393 (19) | 0.0150 (2) | 0.0141 (2) | 0.00099 (17) | 0.00017 (19) | 0.00013 (19) |
S2 | 0.0221 (2) | 0.0173 (2) | 0.0209 (2) | 0.00575 (18) | 0.0001 (2) | −0.0006 (2) |
C1—O1 | 1.455 (2) | C7—H7 | 0.9500 |
C1—H1A | 0.9800 | C8—C9 | 1.378 (3) |
C1—H1B | 0.9800 | C8—H8 | 0.9500 |
C1—H1C | 0.9800 | C9—C10 | 1.387 (3) |
C2—O2 | 1.443 (2) | C9—H9 | 0.9500 |
C2—H2A | 0.9800 | C10—H10 | 0.9500 |
C2—H2B | 0.9800 | C11—C16 | 1.390 (2) |
C2—H2C | 0.9800 | C11—C12 | 1.390 (2) |
C3—N1 | 1.483 (2) | C12—C13 | 1.380 (3) |
C3—C5 | 1.510 (2) | C12—H12 | 0.9500 |
C3—H3A | 0.9900 | C13—C14 | 1.390 (3) |
C3—H3B | 0.9900 | C13—H13 | 0.9500 |
C4—N1 | 1.479 (2) | C14—C15 | 1.377 (3) |
C4—C11 | 1.513 (2) | C14—H14 | 0.9500 |
C4—H4A | 0.9900 | C15—C16 | 1.389 (3) |
C4—H4B | 0.9900 | C15—H15 | 0.9500 |
C5—C6 | 1.389 (2) | C16—H16 | 0.9500 |
C5—C10 | 1.392 (2) | N1—P1 | 1.6343 (15) |
C6—C7 | 1.395 (3) | O1—P1 | 1.5796 (12) |
C6—H6 | 0.9500 | O2—P1 | 1.5961 (12) |
C7—C8 | 1.384 (3) | P1—S2 | 1.9299 (6) |
O1—C1—H1A | 109.5 | C8—C9—C10 | 120.25 (18) |
O1—C1—H1B | 109.5 | C8—C9—H9 | 119.9 |
H1A—C1—H1B | 109.5 | C10—C9—H9 | 119.9 |
O1—C1—H1C | 109.5 | C9—C10—C5 | 120.73 (18) |
H1A—C1—H1C | 109.5 | C9—C10—H10 | 119.6 |
H1B—C1—H1C | 109.5 | C5—C10—H10 | 119.6 |
O2—C2—H2A | 109.5 | C16—C11—C12 | 118.45 (16) |
O2—C2—H2B | 109.5 | C16—C11—C4 | 121.75 (16) |
H2A—C2—H2B | 109.5 | C12—C11—C4 | 119.79 (16) |
O2—C2—H2C | 109.5 | C13—C12—C11 | 121.18 (18) |
H2A—C2—H2C | 109.5 | C13—C12—H12 | 119.4 |
H2B—C2—H2C | 109.5 | C11—C12—H12 | 119.4 |
N1—C3—C5 | 111.89 (13) | C12—C13—C14 | 119.78 (18) |
N1—C3—H3A | 109.2 | C12—C13—H13 | 120.1 |
C5—C3—H3A | 109.2 | C14—C13—H13 | 120.1 |
N1—C3—H3B | 109.2 | C15—C14—C13 | 119.71 (17) |
C5—C3—H3B | 109.2 | C15—C14—H14 | 120.1 |
H3A—C3—H3B | 107.9 | C13—C14—H14 | 120.1 |
N1—C4—C11 | 114.15 (14) | C14—C15—C16 | 120.36 (17) |
N1—C4—H4A | 108.7 | C14—C15—H15 | 119.8 |
C11—C4—H4A | 108.7 | C16—C15—H15 | 119.8 |
N1—C4—H4B | 108.7 | C15—C16—C11 | 120.51 (17) |
C11—C4—H4B | 108.7 | C15—C16—H16 | 119.7 |
H4A—C4—H4B | 107.6 | C11—C16—H16 | 119.7 |
C6—C5—C10 | 118.53 (17) | C4—N1—C3 | 114.98 (13) |
C6—C5—C3 | 121.21 (16) | C4—N1—P1 | 123.50 (11) |
C10—C5—C3 | 120.26 (17) | C3—N1—P1 | 119.30 (11) |
C5—C6—C7 | 120.77 (17) | C1—O1—P1 | 119.78 (11) |
C5—C6—H6 | 119.6 | C2—O2—P1 | 119.39 (12) |
C7—C6—H6 | 119.6 | O1—P1—O2 | 99.37 (7) |
C8—C7—C6 | 119.81 (18) | O1—P1—N1 | 104.62 (7) |
C8—C7—H7 | 120.1 | O2—P1—N1 | 105.89 (7) |
C6—C7—H7 | 120.1 | O1—P1—S2 | 115.68 (5) |
C9—C8—C7 | 119.91 (18) | O2—P1—S2 | 114.41 (5) |
C9—C8—H8 | 120.0 | N1—P1—S2 | 115.14 (6) |
C7—C8—H8 | 120.0 | ||
N1—C3—C5—C6 | 101.64 (19) | C12—C11—C16—C15 | −0.2 (2) |
N1—C3—C5—C10 | −79.63 (19) | C4—C11—C16—C15 | 179.07 (16) |
C10—C5—C6—C7 | 0.6 (3) | C11—C4—N1—C3 | −68.76 (18) |
C3—C5—C6—C7 | 179.38 (16) | C11—C4—N1—P1 | 94.17 (17) |
C5—C6—C7—C8 | 0.0 (3) | C5—C3—N1—C4 | −75.77 (18) |
C6—C7—C8—C9 | −0.6 (3) | C5—C3—N1—P1 | 120.53 (14) |
C7—C8—C9—C10 | 0.5 (3) | C1—O1—P1—O2 | −61.56 (14) |
C8—C9—C10—C5 | 0.1 (3) | C1—O1—P1—N1 | −170.81 (13) |
C6—C5—C10—C9 | −0.7 (3) | C1—O1—P1—S2 | 61.40 (14) |
C3—C5—C10—C9 | −179.47 (16) | C2—O2—P1—O1 | 166.17 (12) |
N1—C4—C11—C16 | 107.68 (18) | C2—O2—P1—N1 | −85.59 (14) |
N1—C4—C11—C12 | −73.1 (2) | C2—O2—P1—S2 | 42.31 (14) |
C16—C11—C12—C13 | 0.0 (3) | C4—N1—P1—O1 | −108.86 (14) |
C4—C11—C12—C13 | −179.28 (16) | C3—N1—P1—O1 | 53.38 (13) |
C11—C12—C13—C14 | 0.5 (3) | C4—N1—P1—O2 | 146.71 (13) |
C12—C13—C14—C15 | −0.8 (3) | C3—N1—P1—O2 | −51.06 (14) |
C13—C14—C15—C16 | 0.7 (3) | C4—N1—P1—S2 | 19.25 (16) |
C14—C15—C16—C11 | −0.1 (3) | C3—N1—P1—S2 | −178.52 (10) |
Experimental details
Crystal data | |
Chemical formula | C16H20NO2PS |
Mr | 321.36 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 120 |
a, b, c (Å) | 6.8377 (3), 8.1115 (4), 28.6187 (16) |
V (Å3) | 1587.31 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.75 × 0.55 × 0.25 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Sapphire2 diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.802, 0.927 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4397, 3010, 2747 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.654 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.064, 1.03 |
No. of reflections | 3010 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.31 |
Absolute structure | Flack (1983), 982 Friedel pairs |
Absolute structure parameter | −0.04 (7) |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), enCIFer (Allen et al., 2004).
Acknowledgements
Support of this investigation by the Islamic Azad University, North Tehran Branch, is gratefully acknowledged.
References
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Pourayoubi, M., Jasinski, J. P., Shoghpour Bayraq, S., Eshghi, H., Keeley, A. C., Bruno, G. & Amiri Rudbari, H. (2012). Acta Cryst. C68, o399–o404. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sabbaghi, F., Pourayoubi, M. & Nečas, M. (2012). Acta Cryst. E68, o2891. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The structure determination of the title compound (Fig. 1) was performed as a part of a project on the synthesis of a new phosphoramidothioate (Sabbaghi et al., 2012). The P═S (1.9299 (6) Å), P—O (1.5796 (12) and 1.5961 (12) Å) and P—N (1.6343 (15) Å) bond lengths are within the expected values. The P atom has a distorted tetrahedral configuration (Fig. 1). The bond angles at the P atom vary in the range 99.37 (7) (O1—P1—O2) to 115.68 (5)° (O1—P1—S2). The nitrogen atom shows sp2 character with the average bond angle 119.3° with the C—N—C angle (114.98 (13) Å) contracted relative to the P—N—C angles (123.50 (11) and 119.30 (11) Å) similar to previously reported compounds with a P—N(CH2C6H5)2 fragment (Pourayoubi et al., 2012).