organic compounds
O,O′-Dimethyl (cyclohexylamido)thiophosphate
aDepartment of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran, bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and cDepartment of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, Brno CZ-61137, Czech Republic
*Correspondence e-mail: fahimeh_sabbaghi@yahoo.com
The P atom in the title compound, C8H18NO2PS, is bonded in a distorted tetrahedral PSO2N environment with bond angles in the range of 99.23 (5)–115.17 (4)°. The cyclohexane ring is disordered over two sets of sites with refined occupancies of 0.528 (5) and 0.472 (5). The ring in both disorder components adopts a chair conformation with the N—H group oriented equatorially. In the crystal, pairs of P=S⋯H—N hydrogen bonds form inversion dimers.
Related literature
For related structures, see: Chivers et al. (2003); Balazs et al. (1999); García-Hernández et al. (2006). For compounds with a P(S)(N)(O)2 skeleton, see: García-Hernández et al. (2006). For the distorted tetrahedral configuration of phosphoramidates and their chalco-derivatives, see: Rudd et al. (1996).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).
Supporting information
https://doi.org/10.1107/S160053681203766X/lh5513sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203766X/lh5513Isup2.hkl
To a solution of [CH3O]2P(S)Cl (1.7 mmol) in dry CH3CN (30 ml), a solution of cyclohexylamine (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 at 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. Nitrogen bound H atom was located in a difference Fourier map and refined isotropically. The disordered cyclohexyl group was modeled over two sites using similarity restraints on anisotropic displacement parameters. To maintain a correct hydrogen geometry, a dummy atom with zero occupancy was created and constrained to share the same site (EXYZ) and anisotropic displacement parameters (EADP) with a fully occupied carbon atom bound to N1.
The ═S bond (Chivers et al., 2003; Balazs et al., 1999; García-Hernández et al., 2006).
of the title compound (Fig. 1) was performed as a part of a project on the synthesis of a new phosphorus(V)-nitrogen compound belonging to the family of phosphoramidothioate with potential applications as S-donor ligands, similar to those observed for reported compounds with a PThe P═S (1.9351 (5) Å), P—O (1.5823 (10) and 1.5853 (9) Å) and P—N (1.6153 (12) Å) bond lengths are within the expected values for compounds with a P(S)(N)(O)2 skeleton (García-Hernández et al., 2006).
The P atom has a distorted tetrahedral configuration (Fig. 1) as it has been noted for phosphoramidates and their chalco-derivatives (Rudd et al., 1996). The bond angles at the P atom vary in the range 99.23 (5) [O1—P1—O2] to 115.17 (4)° [O1—P1—S1]. The C—O—P bond angles are 120.01 (9) [C1—O1—P1] and 119.12 (9)° [C2—O2—P1]. In the crystal, inversion dimers are formed by pairs of P═S···H—N hydrogen bonds, Table 1 and Fig. 2.
For related structures, see: Chivers et al. (2003); Balazs et al. (1999); García-Hernández et al. (2006). For compounds with a P(S)(N)(O)2 skeleton, see: García-Hernández et al. (2006). For the distorted tetrahedral configuration of phosphoramidates and their chalco-derivatives, see: Rudd et al. (1996).
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: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).C8H18NO2PS | Z = 2 |
Mr = 223.26 | F(000) = 240 |
Triclinic, P1 | Dx = 1.296 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.5214 (4) Å | Cell parameters from 2495 reflections |
b = 9.2078 (6) Å | θ = 3.2–27.7° |
c = 10.5763 (7) Å | µ = 0.40 mm−1 |
α = 67.447 (6)° | T = 120 K |
β = 80.212 (5)° | Prism, colourless |
γ = 78.863 (5)° | 0.50 × 0.50 × 0.30 mm |
V = 572.24 (6) Å3 |
Oxford Diffraction Xcalibur Sapphire2 diffractometer | 2017 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1731 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
Detector resolution: 8.4353 pixels mm-1 | θmax = 25.0°, θmin = 3.2° |
ω scan | h = −6→7 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | k = −10→10 |
Tmin = 0.942, Tmax = 1.000 | l = −11→12 |
3413 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0424P)2] where P = (Fo2 + 2Fc2)/3 |
2017 reflections | (Δ/σ)max < 0.001 |
170 parameters | Δρmax = 0.21 e Å−3 |
163 restraints | Δρmin = −0.33 e Å−3 |
C8H18NO2PS | γ = 78.863 (5)° |
Mr = 223.26 | V = 572.24 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.5214 (4) Å | Mo Kα radiation |
b = 9.2078 (6) Å | µ = 0.40 mm−1 |
c = 10.5763 (7) Å | T = 120 K |
α = 67.447 (6)° | 0.50 × 0.50 × 0.30 mm |
β = 80.212 (5)° |
Oxford Diffraction Xcalibur Sapphire2 diffractometer | 2017 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 1731 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 1.000 | Rint = 0.011 |
3413 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 163 restraints |
wR(F2) = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.21 e Å−3 |
2017 reflections | Δρmin = −0.33 e Å−3 |
170 parameters |
Experimental. IR (KBr, cm-1): 3298, 2924, 2852, 1441, 1296, 1237, 1189, 1096, 1043, 926, 800, 644. |
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 | Occ. (<1) | |
S1 | 0.70121 (6) | −0.24913 (4) | 0.59384 (4) | 0.02256 (13) | |
P1 | 0.79402 (5) | −0.18144 (4) | 0.39881 (4) | 0.01557 (12) | |
O1 | 0.71651 (15) | −0.27186 (11) | 0.31916 (10) | 0.0220 (3) | |
O2 | 1.03994 (14) | −0.21705 (11) | 0.36207 (10) | 0.0185 (2) | |
N1 | 0.7238 (2) | 0.00511 (14) | 0.31544 (13) | 0.0186 (3) | |
C1 | 0.7583 (3) | −0.44339 (18) | 0.36569 (19) | 0.0353 (4) | |
H1B | 0.6703 | −0.4816 | 0.3219 | 0.053* | |
H1C | 0.7260 | −0.4884 | 0.4659 | 0.053* | |
H1D | 0.9068 | −0.4763 | 0.3407 | 0.053* | |
C2 | 1.1800 (2) | −0.15705 (18) | 0.41653 (17) | 0.0270 (4) | |
H2A | 1.3260 | −0.1927 | 0.3884 | 0.041* | |
H2B | 1.1550 | −0.1971 | 0.5173 | 0.041* | |
H2C | 1.1541 | −0.0407 | 0.3809 | 0.041* | |
C3A | 0.7713 (2) | 0.08687 (16) | 0.16597 (15) | 0.0193 (3) | |
H3A | 0.8465 | 0.0061 | 0.1261 | 0.023* | 0.528 (5) |
C4A | 0.5781 (5) | 0.1703 (6) | 0.0909 (3) | 0.0248 (9) | 0.528 (5) |
H4A1 | 0.4971 | 0.2458 | 0.1332 | 0.030* | 0.528 (5) |
H4A2 | 0.4873 | 0.0906 | 0.1020 | 0.030* | 0.528 (5) |
C5A | 0.6336 (6) | 0.2606 (7) | −0.0631 (4) | 0.0305 (12) | 0.528 (5) |
H5A1 | 0.7026 | 0.1841 | −0.1076 | 0.037* | 0.528 (5) |
H5A2 | 0.5031 | 0.3161 | −0.1064 | 0.037* | 0.528 (5) |
C6A | 0.7785 (8) | 0.3804 (5) | −0.0864 (4) | 0.0309 (11) | 0.528 (5) |
H6A1 | 0.7043 | 0.4631 | −0.0501 | 0.037* | 0.528 (5) |
H6A2 | 0.8168 | 0.4328 | −0.1865 | 0.037* | 0.528 (5) |
C7A | 0.9772 (7) | 0.3018 (4) | −0.0158 (4) | 0.0251 (9) | 0.528 (5) |
H7A1 | 1.0658 | 0.3835 | −0.0290 | 0.030* | 0.528 (5) |
H7A2 | 1.0585 | 0.2260 | −0.0578 | 0.030* | 0.528 (5) |
C8A | 0.9216 (7) | 0.2137 (5) | 0.1383 (4) | 0.0235 (9) | 0.528 (5) |
H8A1 | 0.8522 | 0.2914 | 0.1814 | 0.028* | 0.528 (5) |
H8A2 | 1.0524 | 0.1596 | 0.1818 | 0.028* | 0.528 (5) |
H3B | 0.8963 | 0.0240 | 0.1326 | 0.023* | 0.472 (5) |
C4B | 0.5791 (6) | 0.0888 (6) | 0.0963 (4) | 0.0202 (9) | 0.472 (5) |
H4B1 | 0.5555 | −0.0214 | 0.1169 | 0.024* | 0.472 (5) |
H4B2 | 0.4515 | 0.1442 | 0.1329 | 0.024* | 0.472 (5) |
C5B | 0.6199 (7) | 0.1738 (6) | −0.0588 (4) | 0.0237 (10) | 0.472 (5) |
H5B1 | 0.7365 | 0.1106 | −0.0964 | 0.028* | 0.472 (5) |
H5B2 | 0.4929 | 0.1831 | −0.1025 | 0.028* | 0.472 (5) |
C6B | 0.6762 (10) | 0.3388 (6) | −0.0932 (5) | 0.0257 (12) | 0.472 (5) |
H6B1 | 0.7101 | 0.3888 | −0.1940 | 0.031* | 0.472 (5) |
H6B2 | 0.5536 | 0.4057 | −0.0646 | 0.031* | 0.472 (5) |
C7B | 0.8621 (10) | 0.3311 (6) | −0.0215 (5) | 0.0299 (11) | 0.472 (5) |
H7B1 | 0.8908 | 0.4402 | −0.0426 | 0.036* | 0.472 (5) |
H7B2 | 0.9880 | 0.2730 | −0.0569 | 0.036* | 0.472 (5) |
C8B | 0.8214 (9) | 0.2479 (5) | 0.1350 (4) | 0.0250 (10) | 0.472 (5) |
H8B1 | 0.9475 | 0.2403 | 0.1789 | 0.030* | 0.472 (5) |
H8B2 | 0.7026 | 0.3100 | 0.1722 | 0.030* | 0.472 (5) |
H1N | 0.634 (2) | 0.0509 (18) | 0.3521 (16) | 0.021 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0223 (2) | 0.0192 (2) | 0.0187 (2) | 0.00165 (15) | 0.00233 (15) | −0.00272 (16) |
P1 | 0.0129 (2) | 0.0147 (2) | 0.0178 (2) | 0.00016 (14) | −0.00189 (15) | −0.00541 (16) |
O1 | 0.0211 (5) | 0.0169 (5) | 0.0302 (6) | 0.0007 (4) | −0.0100 (5) | −0.0095 (5) |
O2 | 0.0130 (5) | 0.0207 (5) | 0.0226 (6) | −0.0006 (4) | −0.0017 (4) | −0.0097 (4) |
N1 | 0.0186 (6) | 0.0164 (7) | 0.0174 (7) | 0.0025 (5) | 0.0009 (5) | −0.0060 (5) |
C1 | 0.0376 (10) | 0.0200 (9) | 0.0541 (12) | 0.0017 (7) | −0.0183 (9) | −0.0170 (8) |
C2 | 0.0171 (8) | 0.0286 (9) | 0.0380 (10) | −0.0048 (6) | −0.0065 (7) | −0.0126 (8) |
C3A | 0.0214 (8) | 0.0181 (8) | 0.0163 (8) | 0.0006 (6) | −0.0008 (6) | −0.0059 (6) |
C4A | 0.0235 (16) | 0.030 (2) | 0.0192 (16) | −0.0038 (17) | −0.0037 (12) | −0.0069 (17) |
C5A | 0.026 (2) | 0.044 (4) | 0.0176 (19) | −0.005 (3) | −0.0063 (15) | −0.005 (2) |
C6A | 0.031 (3) | 0.026 (2) | 0.023 (2) | −0.0014 (19) | 0.0021 (18) | 0.0004 (16) |
C7A | 0.027 (2) | 0.0221 (18) | 0.0242 (18) | −0.0088 (17) | 0.0028 (18) | −0.0068 (14) |
C8A | 0.026 (2) | 0.021 (2) | 0.0226 (17) | −0.0055 (17) | −0.0026 (18) | −0.0059 (14) |
C3B | 0.0214 (8) | 0.0181 (8) | 0.0163 (8) | 0.0006 (6) | −0.0008 (6) | −0.0059 (6) |
C4B | 0.0229 (17) | 0.017 (2) | 0.0189 (18) | −0.0018 (18) | −0.0045 (13) | −0.0045 (17) |
C5B | 0.031 (2) | 0.021 (2) | 0.0209 (18) | −0.0037 (18) | −0.0053 (14) | −0.0081 (18) |
C6B | 0.038 (3) | 0.017 (3) | 0.018 (2) | −0.005 (2) | −0.003 (2) | −0.0017 (19) |
C7B | 0.037 (3) | 0.024 (2) | 0.028 (2) | −0.015 (2) | −0.004 (2) | −0.0028 (18) |
C8B | 0.031 (3) | 0.021 (2) | 0.0230 (19) | −0.007 (2) | −0.006 (2) | −0.0051 (16) |
S1—P1 | 1.9351 (5) | C6A—C7A | 1.521 (5) |
P1—O1 | 1.5823 (10) | C6A—H6A1 | 0.9900 |
P1—O2 | 1.5853 (9) | C6A—H6A2 | 0.9900 |
P1—N1 | 1.6153 (12) | C7A—C8A | 1.531 (5) |
O1—C1 | 1.4471 (18) | C7A—H7A1 | 0.9900 |
O2—C2 | 1.4456 (17) | C7A—H7A2 | 0.9900 |
N1—C3A | 1.4739 (18) | C8A—H8A1 | 0.9900 |
N1—H1N | 0.791 (16) | C8A—H8A2 | 0.9900 |
C1—H1B | 0.9800 | C4B—C5B | 1.523 (5) |
C1—H1C | 0.9800 | C4B—H4B1 | 0.9900 |
C1—H1D | 0.9800 | C4B—H4B2 | 0.9900 |
C2—H2A | 0.9800 | C5B—C6B | 1.523 (5) |
C2—H2B | 0.9800 | C5B—H5B1 | 0.9900 |
C2—H2C | 0.9800 | C5B—H5B2 | 0.9900 |
C3A—C4A | 1.519 (4) | C6B—C7B | 1.513 (6) |
C3A—C8A | 1.578 (4) | C6B—H6B1 | 0.9900 |
C3A—H3A | 1.0000 | C6B—H6B2 | 0.9900 |
C4A—C5A | 1.533 (5) | C7B—C8B | 1.534 (6) |
C4A—H4A1 | 0.9900 | C7B—H7B1 | 0.9900 |
C4A—H4A2 | 0.9900 | C7B—H7B2 | 0.9900 |
C5A—C6A | 1.512 (6) | C8B—H8B1 | 0.9900 |
C5A—H5A1 | 0.9900 | C8B—H8B2 | 0.9900 |
C5A—H5A2 | 0.9900 | ||
O1—P1—O2 | 99.23 (5) | C5A—C6A—H6A1 | 109.4 |
O1—P1—N1 | 105.48 (6) | C7A—C6A—H6A1 | 109.4 |
O2—P1—N1 | 107.01 (6) | C5A—C6A—H6A2 | 109.4 |
O1—P1—S1 | 115.17 (4) | C7A—C6A—H6A2 | 109.4 |
O2—P1—S1 | 114.80 (4) | H6A1—C6A—H6A2 | 108.0 |
N1—P1—S1 | 113.73 (5) | C6A—C7A—C8A | 110.4 (3) |
C1—O1—P1 | 120.01 (9) | C6A—C7A—H7A1 | 109.6 |
C2—O2—P1 | 119.12 (9) | C8A—C7A—H7A1 | 109.6 |
C3A—N1—P1 | 124.89 (10) | C6A—C7A—H7A2 | 109.6 |
C3A—N1—H1N | 115.6 (11) | C8A—C7A—H7A2 | 109.6 |
P1—N1—H1N | 117.5 (11) | H7A1—C7A—H7A2 | 108.1 |
O1—C1—H1B | 109.5 | C7A—C8A—C3A | 112.0 (3) |
O1—C1—H1C | 109.5 | C7A—C8A—H8A1 | 109.2 |
H1B—C1—H1C | 109.5 | C3A—C8A—H8A1 | 109.2 |
O1—C1—H1D | 109.5 | C7A—C8A—H8A2 | 109.2 |
H1B—C1—H1D | 109.5 | C3A—C8A—H8A2 | 109.2 |
H1C—C1—H1D | 109.5 | H8A1—C8A—H8A2 | 107.9 |
O2—C2—H2A | 109.5 | C5B—C4B—H4B1 | 109.8 |
O2—C2—H2B | 109.5 | C5B—C4B—H4B2 | 109.8 |
H2A—C2—H2B | 109.5 | H4B1—C4B—H4B2 | 108.3 |
O2—C2—H2C | 109.5 | C6B—C5B—C4B | 111.1 (3) |
H2A—C2—H2C | 109.5 | C6B—C5B—H5B1 | 109.4 |
H2B—C2—H2C | 109.5 | C4B—C5B—H5B1 | 109.4 |
N1—C3A—C4A | 113.92 (16) | C6B—C5B—H5B2 | 109.4 |
N1—C3A—C8A | 109.76 (17) | C4B—C5B—H5B2 | 109.4 |
C4A—C3A—C8A | 108.4 (2) | H5B1—C5B—H5B2 | 108.0 |
N1—C3A—H3A | 108.2 | C7B—C6B—C5B | 111.3 (4) |
C4A—C3A—H3A | 108.2 | C7B—C6B—H6B1 | 109.4 |
C8A—C3A—H3A | 108.2 | C5B—C6B—H6B1 | 109.4 |
C3A—C4A—C5A | 112.6 (3) | C7B—C6B—H6B2 | 109.4 |
C3A—C4A—H4A1 | 109.1 | C5B—C6B—H6B2 | 109.4 |
C5A—C4A—H4A1 | 109.1 | H6B1—C6B—H6B2 | 108.0 |
C3A—C4A—H4A2 | 109.1 | C6B—C7B—C8B | 111.5 (4) |
C5A—C4A—H4A2 | 109.1 | C6B—C7B—H7B1 | 109.3 |
H4A1—C4A—H4A2 | 107.8 | C8B—C7B—H7B1 | 109.3 |
C6A—C5A—C4A | 111.4 (3) | C6B—C7B—H7B2 | 109.3 |
C6A—C5A—H5A1 | 109.3 | C8B—C7B—H7B2 | 109.3 |
C4A—C5A—H5A1 | 109.3 | H7B1—C7B—H7B2 | 108.0 |
C6A—C5A—H5A2 | 109.3 | C7B—C8B—H8B1 | 109.8 |
C4A—C5A—H5A2 | 109.3 | C7B—C8B—H8B2 | 109.8 |
H5A1—C5A—H5A2 | 108.0 | H8B1—C8B—H8B2 | 108.3 |
C5A—C6A—C7A | 111.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···S1i | 0.791 (16) | 2.695 (17) | 3.4633 (13) | 164.3 (14) |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C8H18NO2PS |
Mr | 223.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 6.5214 (4), 9.2078 (6), 10.5763 (7) |
α, β, γ (°) | 67.447 (6), 80.212 (5), 78.863 (5) |
V (Å3) | 572.24 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.50 × 0.50 × 0.30 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Sapphire2 |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.942, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3413, 2017, 1731 |
Rint | 0.011 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.069, 1.07 |
No. of reflections | 2017 |
No. of parameters | 170 |
No. of restraints | 163 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.33 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···S1i | 0.791 (16) | 2.695 (17) | 3.4633 (13) | 164.3 (14) |
Symmetry code: (i) −x+1, −y, −z+1. |
Acknowledgements
Support of this investigation by the Zanjan Branch, Islamic Azad University, is gratefully acknowledged.
References
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The structure determination of the title compound (Fig. 1) was performed as a part of a project on the synthesis of a new phosphorus(V)-nitrogen compound belonging to the family of phosphoramidothioate with potential applications as S-donor ligands, similar to those observed for reported compounds with a P═S bond (Chivers et al., 2003; Balazs et al., 1999; García-Hernández et al., 2006).
The P═S (1.9351 (5) Å), P—O (1.5823 (10) and 1.5853 (9) Å) and P—N (1.6153 (12) Å) bond lengths are within the expected values for compounds with a P(S)(N)(O)2 skeleton (García-Hernández et al., 2006).
The P atom has a distorted tetrahedral configuration (Fig. 1) as it has been noted for phosphoramidates and their chalco-derivatives (Rudd et al., 1996). The bond angles at the P atom vary in the range 99.23 (5) [O1—P1—O2] to 115.17 (4)° [O1—P1—S1]. The C—O—P bond angles are 120.01 (9) [C1—O1—P1] and 119.12 (9)° [C2—O2—P1]. In the crystal, inversion dimers are formed by pairs of P═S···H—N hydrogen bonds, Table 1 and Fig. 2.