organic compounds
Diphenyl (isopropylamido)phosphate
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, C15H18NO3P, is in a distorted tetrahedral P(O)(O)2N environment; the bond angles at P are in the range 98.16 (6)–115.82 (6)°. In the crystal, adjacent molecules are linked via N—H⋯O=P hydrogen bonds into a chain running parallel to the b axis. The methyl groups are disordered over two sets of sites in a 0.677 (14):0.323 (14) ratio. The crystal studied was a non-merohedral twin with a refined minor component of 22.31 (4)%.
Experimental
Crystal data
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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: 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: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).
Supporting information
10.1107/S1600536812047940/ff2090sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047940/ff2090Isup2.hkl
To a solution of [C6H5O]2P(O)Cl (2 mmol) in dry CH3CN (30 ml), a solution of isopropylamine (4 mmol) in the same solvent (5 ml) was added at ice bath temperature under stirring. After 4 h, the solvent was removed and the product was washed with distilled water and recrystallized from CH3CN/n-C6H14 (4:1) at room temperature. The single crystals suitable for X-ray analysis were obtained from this solution after a few days at room temperature.
The crystal sample was non-merohedrally twinned. Using data reduction software, a HKLF 5 file was produced for a two-component twin and used in the
The fractional contribution of the minor twin component converged to 0.2231 (4). 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 its position was refined while the N—H distance was fixed at 0.88 Å and the Uiso set to 1.2Ueq of N1. The disordered methyl groups were modeled over two sites while restraining their anisotropic displacement parameters to be approximately isotropic (ISOR). 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.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: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).C15H18NO3P | F(000) = 308 |
Mr = 291.27 | Dx = 1.322 Mg m−3 |
Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4432 (5) Å | Cell parameters from 3821 reflections |
b = 5.3030 (4) Å | θ = 3.4–27.5° |
c = 16.3443 (11) Å | µ = 0.19 mm−1 |
β = 90.453 (6)° | T = 120 K |
V = 731.78 (9) Å3 | Block, colourless |
Z = 2 | 0.45 × 0.42 × 0.40 mm |
Oxford Diffraction Xcalibur (Sapphire2) diffractometer | 6226 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 6040 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
Detector resolution: 8.4353 pixels mm-1 | θmax = 25.0°, θmin = 3.8° |
ω scan | h = −10→10 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | k = −6→6 |
Tmin = 0.918, Tmax = 0.926 | l = −19→19 |
6226 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 atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0626P)2 + 0.0183P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
6226 reflections | Δρmax = 0.17 e Å−3 |
208 parameters | Δρmin = −0.18 e Å−3 |
28 restraints | Absolute structure: Flack (1983), 1229 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (6) |
C15H18NO3P | V = 731.78 (9) Å3 |
Mr = 291.27 | Z = 2 |
Monoclinic, Pn | Mo Kα radiation |
a = 8.4432 (5) Å | µ = 0.19 mm−1 |
b = 5.3030 (4) Å | T = 120 K |
c = 16.3443 (11) Å | 0.45 × 0.42 × 0.40 mm |
β = 90.453 (6)° |
Oxford Diffraction Xcalibur (Sapphire2) diffractometer | 6226 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 6040 reflections with I > 2σ(I) |
Tmin = 0.918, Tmax = 0.926 | Rint = 0.000 |
6226 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | Δρmax = 0.17 e Å−3 |
S = 1.06 | Δρmin = −0.18 e Å−3 |
6226 reflections | Absolute structure: Flack (1983), 1229 Friedel pairs |
208 parameters | Absolute structure parameter: 0.05 (6) |
28 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 | Occ. (<1) | |
P1 | 0.49359 (4) | 0.20465 (6) | 0.51025 (3) | 0.01893 (9) | |
O1 | 0.46890 (12) | 0.20756 (19) | 0.41396 (6) | 0.0229 (3) | |
O2 | 0.32869 (12) | 0.3259 (2) | 0.53519 (6) | 0.0213 (2) | |
O3 | 0.52704 (12) | −0.04455 (19) | 0.54422 (6) | 0.0247 (3) | |
N1 | 0.62616 (15) | 0.4126 (2) | 0.53057 (8) | 0.0201 (3) | |
H1N | 0.603 (2) | 0.559 (3) | 0.5224 (10) | 0.024* | |
C1 | 0.33996 (19) | 0.0959 (3) | 0.37348 (10) | 0.0241 (4) | |
C2 | 0.2687 (2) | −0.1207 (3) | 0.40086 (13) | 0.0346 (4) | |
H2 | 0.3036 | −0.2017 | 0.4496 | 0.042* | |
C3 | 0.1433 (2) | −0.2176 (3) | 0.35464 (15) | 0.0454 (6) | |
H3 | 0.0915 | −0.3663 | 0.3727 | 0.054* | |
C4 | 0.0931 (2) | −0.1044 (4) | 0.28402 (14) | 0.0489 (6) | |
H4 | 0.0066 | −0.1725 | 0.2537 | 0.059* | |
C5 | 0.1686 (2) | 0.1079 (4) | 0.25735 (13) | 0.0440 (5) | |
H5 | 0.1359 | 0.1848 | 0.2075 | 0.053* | |
C6 | 0.2921 (2) | 0.2121 (3) | 0.30207 (11) | 0.0307 (4) | |
H6 | 0.3430 | 0.3614 | 0.2838 | 0.037* | |
C7 | 0.27851 (18) | 0.3331 (3) | 0.61695 (10) | 0.0197 (4) | |
C8 | 0.31935 (19) | 0.5376 (3) | 0.66473 (9) | 0.0244 (4) | |
H8 | 0.3868 | 0.6656 | 0.6441 | 0.029* | |
C9 | 0.2607 (2) | 0.5528 (3) | 0.74285 (10) | 0.0319 (4) | |
H9 | 0.2874 | 0.6928 | 0.7765 | 0.038* | |
C10 | 0.1630 (2) | 0.3656 (4) | 0.77258 (11) | 0.0376 (5) | |
H10 | 0.1232 | 0.3763 | 0.8267 | 0.045* | |
C11 | 0.1238 (2) | 0.1643 (3) | 0.72383 (12) | 0.0360 (5) | |
H11 | 0.0562 | 0.0361 | 0.7443 | 0.043* | |
C12 | 0.1817 (2) | 0.1460 (3) | 0.64507 (12) | 0.0306 (4) | |
H12 | 0.1547 | 0.0065 | 0.6113 | 0.037* | |
C13A | 0.79551 (19) | 0.3558 (3) | 0.54259 (10) | 0.0212 (4) | |
H13A | 0.8017 | 0.1911 | 0.5722 | 0.025* | 0.323 (14) |
C14A | 0.8579 (13) | 0.557 (2) | 0.6011 (9) | 0.042 (3) | 0.323 (14) |
H14A | 0.8401 | 0.7242 | 0.5773 | 0.064* | 0.323 (14) |
H14B | 0.9716 | 0.5312 | 0.6104 | 0.064* | 0.323 (14) |
H14C | 0.8021 | 0.5444 | 0.6533 | 0.064* | 0.323 (14) |
C15A | 0.8791 (19) | 0.324 (3) | 0.4671 (9) | 0.037 (3) | 0.323 (14) |
H15A | 0.8307 | 0.1869 | 0.4355 | 0.056* | 0.323 (14) |
H15B | 0.9902 | 0.2833 | 0.4788 | 0.056* | 0.323 (14) |
H15C | 0.8736 | 0.4808 | 0.4354 | 0.056* | 0.323 (14) |
C13B | 0.79551 (19) | 0.3558 (3) | 0.54259 (10) | 0.0212 (4) | 0.00 |
H13B | 0.8085 | 0.2301 | 0.5878 | 0.025* | 0.677 (14) |
C14B | 0.8824 (4) | 0.5997 (8) | 0.5652 (4) | 0.0306 (11) | 0.677 (14) |
H14D | 0.8633 | 0.7267 | 0.5227 | 0.046* | 0.677 (14) |
H14E | 0.9963 | 0.5662 | 0.5696 | 0.046* | 0.677 (14) |
H14F | 0.8434 | 0.6622 | 0.6177 | 0.046* | 0.677 (14) |
C15B | 0.8680 (8) | 0.2476 (13) | 0.4620 (4) | 0.0298 (11) | 0.677 (14) |
H15D | 0.8160 | 0.0877 | 0.4482 | 0.045* | 0.677 (14) |
H15E | 0.9818 | 0.2188 | 0.4701 | 0.045* | 0.677 (14) |
H15F | 0.8517 | 0.3683 | 0.4174 | 0.045* | 0.677 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.01606 (19) | 0.01911 (19) | 0.02163 (19) | 0.00093 (19) | 0.00011 (14) | 0.0017 (2) |
O1 | 0.0195 (6) | 0.0253 (6) | 0.0238 (6) | −0.0048 (5) | −0.0003 (5) | −0.0003 (5) |
O2 | 0.0173 (6) | 0.0247 (6) | 0.0218 (6) | 0.0019 (5) | −0.0019 (4) | 0.0017 (5) |
O3 | 0.0239 (6) | 0.0191 (6) | 0.0313 (6) | 0.0014 (4) | 0.0029 (5) | 0.0024 (5) |
N1 | 0.0184 (7) | 0.0154 (7) | 0.0265 (8) | 0.0024 (5) | −0.0008 (5) | 0.0027 (6) |
C1 | 0.0155 (8) | 0.0276 (9) | 0.0291 (10) | −0.0002 (7) | 0.0017 (7) | −0.0118 (7) |
C2 | 0.0318 (11) | 0.0258 (9) | 0.0462 (12) | −0.0045 (8) | −0.0004 (8) | −0.0038 (9) |
C3 | 0.0349 (12) | 0.0286 (11) | 0.0727 (17) | −0.0092 (9) | 0.0004 (11) | −0.0148 (11) |
C4 | 0.0245 (11) | 0.0615 (14) | 0.0604 (15) | −0.0062 (10) | −0.0054 (10) | −0.0292 (11) |
C5 | 0.0239 (11) | 0.0722 (16) | 0.0359 (12) | 0.0046 (10) | −0.0064 (8) | −0.0101 (11) |
C6 | 0.0207 (10) | 0.0402 (11) | 0.0313 (10) | 0.0021 (8) | 0.0023 (8) | −0.0036 (9) |
C7 | 0.0137 (9) | 0.0204 (8) | 0.0251 (9) | 0.0058 (6) | 0.0003 (7) | 0.0059 (7) |
C8 | 0.0262 (10) | 0.0223 (8) | 0.0248 (9) | −0.0025 (7) | −0.0027 (7) | 0.0031 (7) |
C9 | 0.0431 (12) | 0.0242 (10) | 0.0284 (10) | 0.0084 (9) | −0.0014 (8) | 0.0006 (8) |
C10 | 0.0368 (12) | 0.0450 (12) | 0.0312 (10) | 0.0186 (9) | 0.0138 (9) | 0.0091 (9) |
C11 | 0.0289 (11) | 0.0336 (11) | 0.0457 (13) | 0.0015 (8) | 0.0162 (9) | 0.0143 (9) |
C12 | 0.0237 (10) | 0.0255 (9) | 0.0427 (11) | 0.0001 (7) | 0.0052 (8) | 0.0003 (8) |
C13A | 0.0166 (9) | 0.0217 (8) | 0.0253 (9) | 0.0034 (6) | −0.0049 (7) | 0.0023 (7) |
C14A | 0.033 (4) | 0.043 (4) | 0.051 (4) | 0.008 (3) | −0.019 (3) | −0.007 (3) |
C15A | 0.030 (4) | 0.038 (5) | 0.043 (4) | 0.010 (4) | −0.006 (3) | −0.011 (4) |
C13B | 0.0166 (9) | 0.0217 (8) | 0.0253 (9) | 0.0034 (6) | −0.0049 (7) | 0.0023 (7) |
C14B | 0.0200 (15) | 0.0309 (18) | 0.041 (2) | 0.0000 (12) | −0.0056 (15) | −0.0077 (16) |
C15B | 0.0230 (18) | 0.035 (3) | 0.0317 (19) | −0.0010 (19) | 0.0069 (14) | −0.007 (2) |
P1—O3 | 1.4602 (11) | C9—C10 | 1.381 (3) |
P1—O1 | 1.5858 (11) | C9—H9 | 0.9500 |
P1—O2 | 1.5896 (11) | C10—C11 | 1.371 (3) |
P1—N1 | 1.6043 (14) | C10—H10 | 0.9500 |
O1—C1 | 1.4008 (19) | C11—C12 | 1.384 (2) |
O2—C7 | 1.4057 (17) | C11—H11 | 0.9500 |
N1—C13A | 1.4728 (19) | C12—H12 | 0.9500 |
N1—H1N | 0.811 (13) | C13A—C15A | 1.436 (15) |
C1—C2 | 1.373 (2) | C13A—C14A | 1.524 (8) |
C1—C6 | 1.378 (2) | C13A—H13A | 1.0000 |
C2—C3 | 1.393 (3) | C14A—H14A | 0.9800 |
C2—H2 | 0.9500 | C14A—H14B | 0.9800 |
C3—C4 | 1.366 (3) | C14A—H14C | 0.9800 |
C3—H3 | 0.9500 | C15A—H15A | 0.9800 |
C4—C5 | 1.367 (3) | C15A—H15B | 0.9800 |
C4—H4 | 0.9500 | C15A—H15C | 0.9800 |
C5—C6 | 1.383 (3) | C14B—H14D | 0.9800 |
C5—H5 | 0.9500 | C14B—H14E | 0.9800 |
C6—H6 | 0.9500 | C14B—H14F | 0.9800 |
C7—C12 | 1.367 (2) | C15B—H15D | 0.9800 |
C7—C8 | 1.379 (2) | C15B—H15E | 0.9800 |
C8—C9 | 1.376 (2) | C15B—H15F | 0.9800 |
C8—H8 | 0.9500 | ||
O3—P1—O1 | 114.19 (6) | C12—C7—O2 | 119.04 (14) |
O3—P1—O2 | 115.82 (6) | C8—C7—O2 | 118.95 (13) |
O1—P1—O2 | 98.16 (6) | C9—C8—C7 | 118.79 (15) |
O3—P1—N1 | 114.26 (7) | C9—C8—H8 | 120.6 |
O1—P1—N1 | 106.55 (6) | C7—C8—H8 | 120.6 |
O2—P1—N1 | 106.26 (6) | C8—C9—C10 | 120.31 (17) |
C1—O1—P1 | 124.07 (10) | C8—C9—H9 | 119.8 |
C7—O2—P1 | 121.74 (10) | C10—C9—H9 | 119.8 |
C13A—N1—P1 | 124.19 (11) | C11—C10—C9 | 119.82 (16) |
C13A—N1—H1N | 116.9 (13) | C11—C10—H10 | 120.1 |
P1—N1—H1N | 117.1 (13) | C9—C10—H10 | 120.1 |
C2—C1—C6 | 121.57 (16) | C10—C11—C12 | 120.63 (15) |
C2—C1—O1 | 122.74 (15) | C10—C11—H11 | 119.7 |
C6—C1—O1 | 115.65 (14) | C12—C11—H11 | 119.7 |
C1—C2—C3 | 117.70 (19) | C7—C12—C11 | 118.59 (17) |
C1—C2—H2 | 121.2 | C7—C12—H12 | 120.7 |
C3—C2—H2 | 121.2 | C11—C12—H12 | 120.7 |
C4—C3—C2 | 121.69 (19) | C15A—C13A—N1 | 113.1 (7) |
C4—C3—H3 | 119.2 | C15A—C13A—C14A | 116.8 (6) |
C2—C3—H3 | 119.2 | N1—C13A—C14A | 105.7 (4) |
C3—C4—C5 | 119.3 (2) | C15A—C13A—H13A | 106.9 |
C3—C4—H4 | 120.4 | N1—C13A—H13A | 106.9 |
C5—C4—H4 | 120.4 | C14A—C13A—H13A | 106.9 |
C4—C5—C6 | 120.8 (2) | H14D—C14B—H14E | 109.5 |
C4—C5—H5 | 119.6 | H14D—C14B—H14F | 109.5 |
C6—C5—H5 | 119.6 | H14E—C14B—H14F | 109.5 |
C1—C6—C5 | 118.93 (17) | H15D—C15B—H15E | 109.5 |
C1—C6—H6 | 120.5 | H15D—C15B—H15F | 109.5 |
C5—C6—H6 | 120.5 | H15E—C15B—H15F | 109.5 |
C12—C7—C8 | 121.86 (15) | ||
O3—P1—O1—C1 | 67.82 (12) | C2—C1—C6—C5 | 0.3 (3) |
O2—P1—O1—C1 | −55.32 (12) | O1—C1—C6—C5 | 177.98 (15) |
N1—P1—O1—C1 | −165.06 (11) | C4—C5—C6—C1 | 1.1 (3) |
O3—P1—O2—C7 | 48.50 (13) | P1—O2—C7—C12 | −95.01 (17) |
O1—P1—O2—C7 | 170.46 (11) | P1—O2—C7—C8 | 89.47 (14) |
N1—P1—O2—C7 | −79.57 (12) | C12—C7—C8—C9 | 0.0 (2) |
O3—P1—N1—C13A | 30.26 (15) | O2—C7—C8—C9 | 175.40 (15) |
O1—P1—N1—C13A | −96.81 (13) | C7—C8—C9—C10 | 0.2 (3) |
O2—P1—N1—C13A | 159.24 (12) | C8—C9—C10—C11 | −0.4 (3) |
P1—O1—C1—C2 | −33.7 (2) | C9—C10—C11—C12 | 0.3 (3) |
P1—O1—C1—C6 | 148.68 (12) | C8—C7—C12—C11 | −0.1 (3) |
C6—C1—C2—C3 | −1.2 (3) | O2—C7—C12—C11 | −175.45 (15) |
O1—C1—C2—C3 | −178.68 (16) | C10—C11—C12—C7 | −0.1 (3) |
C1—C2—C3—C4 | 0.7 (3) | P1—N1—C13A—C15A | 80.0 (6) |
C2—C3—C4—C5 | 0.7 (3) | P1—N1—C13A—C14A | −150.9 (7) |
C3—C4—C5—C6 | −1.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3i | 0.81 (1) | 2.23 (1) | 3.0065 (17) | 161 (2) |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C15H18NO3P |
Mr | 291.27 |
Crystal system, space group | Monoclinic, Pn |
Temperature (K) | 120 |
a, b, c (Å) | 8.4432 (5), 5.3030 (4), 16.3443 (11) |
β (°) | 90.453 (6) |
V (Å3) | 731.78 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.45 × 0.42 × 0.40 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur (Sapphire2) diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.918, 0.926 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6226, 6226, 6040 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.081, 1.06 |
No. of reflections | 6226 |
No. of parameters | 208 |
No. of restraints | 28 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.18 |
Absolute structure | Flack (1983), 1229 Friedel pairs |
Absolute structure parameter | 0.05 (6) |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), 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···O3i | 0.811 (13) | 2.228 (13) | 3.0065 (17) | 161.0 (15) |
Symmetry code: (i) x, y+1, z. |
Acknowledgements
Support of this investigation by Zanjan Branch, Islamic Azad University, is gratefully acknowledged.
References
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This work is a continuation of our studies of phosphoramidate compounds, during which the structures of various diphenyl amido phosphates, for example [C6H5O]2P(O)[NHCH(C2H5)(C6H5)] (Sabbaghi et al., 2011) were reported. Here, we report the synthesis and crystal structure determination of the title compound, [C6H5O]2P(O)[NHCH(CH3)2].
The P═O (1.4602 (11) Å), P—O (1.5858 (11) and 1.5896 (11) Å) and P—N (1.6043 (14) Å) bond lengths are within the expected values (Sabbaghi et al., 2011).
The P atom adopts a distorted tetrahedral configuration (Fig. 1). The bond angles at the P atom vary in the range 98.16 (6) [O1—P1—O2] to 115.82 (6)° [O3—P1—O2].
The C—O—P bond angles (124.07 (10) [C1—O1—P1] and 121.74 (10)° [C7—O2—P1]) and the C13A—N1—P1 (124.19 (11)°) bond angle are standard for this category of phosphoramidate compounds (Sabbaghi et al., 2011).
In the crystal structure, molecules are linked via N—H···O═P hydrogen bonds into extended chains running parallel to the b axis (Table 1).