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Adjacent mol­ecules of the title compound [alternative name: phospho­ric bis(4-methyl­benz­amide) di­methyl­amide], C16H22­N3OP, with tetrahedral phospho­rus, are linked by twin N—H...O [N...O = 2.958 (3) Å] hydrogen bonds into a linear chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001587/cf6140sup1.cif
Contains datablocks I, cf6140

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001587/cf6140Isup2.hkl
Contains datablock I

CCDC reference: 180809

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.156
  • Data-to-parameter ratio = 18.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CELDIM (Enraf-Nonius, 1994); data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

N,N-Dimethyl-N',N''-bis(4-methylphenyl)phosphoramidate top
Crystal data top
C16H22N3OPDx = 1.228 Mg m3
Mr = 303.34Melting point = 164–166 K
Orthorhombic, PnamMo Kα radiation, λ = 0.71073 Å
a = 9.305 (9) ÅCell parameters from 25 reflections
b = 10.101 (2) Åθ = 12.9–18.3°
c = 17.454 (2) ŵ = 0.17 mm1
V = 1641 (2) Å3T = 298 K
Z = 4Block, colorless
F(000) = 6480.42 × 0.21 × 0.10 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
1213 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
ω–2θ scansh = 120
Absorption correction: empirical
ψ scan (North et al., 1968)
k = 013
Tmin = 0.881, Tmax = 0.968l = 220
1939 measured reflections3 standard reflections every 120 min
1939 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.0811P)2 + 0.2692P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1939 reflectionsΔρmax = 0.30 e Å3
105 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (3)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.23185 (8)0.36794 (8)0.25000.0451 (3)
O10.0868 (2)0.3082 (2)0.25000.0592 (7)
N10.3375 (2)0.3255 (2)0.3212 (1)0.0534 (5)
N20.2141 (3)0.5281 (3)0.25000.0605 (8)
C10.3225 (2)0.3585 (2)0.3993 (1)0.0477 (6)
C20.4263 (3)0.3175 (3)0.4507 (2)0.0597 (7)
C30.4169 (3)0.3503 (3)0.5272 (2)0.0676 (8)
C40.3046 (3)0.4256 (3)0.5559 (2)0.0596 (7)
C50.2028 (3)0.4661 (3)0.5040 (2)0.0637 (7)
C60.2095 (2)0.4333 (3)0.4274 (2)0.0631 (7)
C70.2961 (3)0.4655 (3)0.6389 (2)0.0821 (9)
C80.3393 (4)0.6144 (4)0.25000.104 (2)
C90.0769 (4)0.5973 (5)0.25000.088 (2)
H10.41060.27750.30960.064*
H20.50350.26720.43350.072*
H30.48800.32090.56060.081*
H50.12640.51750.52110.076*
H60.13750.46160.39430.076*
H7a0.36870.53040.64960.123*
H7b0.31110.38920.67060.123*
H7c0.20300.50230.64930.123*
H8a0.42510.56170.25000.156*
H8b0.33770.66930.29490.156*
H9a0.00000.53390.25000.131*
H9b0.07010.65180.20510.131*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0286 (4)0.0472 (5)0.0594 (6)0.0036 (3)0.0000.000
O10.036 (1)0.067 (2)0.074 (2)0.018 (1)0.0000.000
N10.040 (1)0.061 (1)0.059 (1)0.012 (1)0.002 (1)0.008 (1)
N20.029 (1)0.049 (2)0.103 (3)0.002 (1)0.0000.000
C10.036 (1)0.048 (1)0.059 (1)0.002 (1)0.003 (1)0.004 (1)
C20.051 (1)0.062 (2)0.066 (2)0.014 (1)0.004 (1)0.004 (1)
C30.061 (2)0.080 (2)0.062 (2)0.013 (1)0.004 (1)0.006 (1)
C40.055 (2)0.065 (2)0.059 (2)0.011 (1)0.006 (1)0.002 (1)
C50.044 (1)0.077 (2)0.070 (2)0.005 (1)0.007 (1)0.016 (2)
C60.038 (1)0.084 (2)0.068 (2)0.010 (1)0.006 (1)0.010 (1)
C70.084 (2)0.098 (2)0.064 (2)0.005 (2)0.009 (2)0.006 (2)
C80.054 (2)0.056 (2)0.202 (6)0.012 (2)0.0000.000
C90.046 (2)0.076 (3)0.141 (4)0.023 (2)0.0000.000
Geometric parameters (Å, º) top
P1—O11.478 (2)C5—C61.379 (4)
P1—N21.626 (3)N1—H10.860
P1—N11.642 (2)C2—H20.930
P1—N1i1.642 (2)C3—H30.930
N1—C11.409 (3)C5—H50.930
N2—C81.455 (5)C6—H60.930
N2—C91.456 (4)C7—H7a0.960
C1—C21.383 (3)C7—H7b0.960
C1—C61.384 (3)C7—H7c0.960
C2—C31.379 (4)C8—H8a0.960
C3—C41.386 (4)C8—H8b0.960
C4—C51.373 (4)C9—H9a0.960
C4—C71.506 (4)C9—H9b0.960
O1—P1—N1116.1 (1)P1—N1—H1116.2
O1—P1—N1i116.1 (1)C3—C2—H2119.6
O1—P1—N2108.3 (1)C1—C2—H2119.6
N1—P1—N1i98.4 (2)C2—C3—H3119.0
N1—P1—N2108.7 (1)C4—C3—H3119.0
N1i—P1—N2108.7 (1)C4—C5—H5118.8
C1—N1—P1127.6 (2)C6—C5—H5118.8
C8—N2—C9114.5 (3)C5—C6—H6119.7
C8—N2—P1121.0 (2)C1—C6—H6119.7
C9—N2—P1124.5 (3)C4—C7—H7a109.5
C2—C1—C6117.6 (3)C4—C7—H7b109.5
C2—C1—N1119.2 (2)H7a—C7—H7b109.5
C6—C1—N1123.2 (2)C4—C7—H7c109.5
C3—C2—C1120.9 (2)H7a—C7—H7c109.5
C2—C3—C4121.9 (3)H7b—C7—H7c109.5
C5—C4—C3116.4 (3)N2—C8—H8a109.5
C5—C4—C7121.2 (3)N2—C8—H8b109.5
C3—C4—C7122.3 (3)H8a—C8—H8b109.5
C4—C5—C6122.5 (2)N2—C9—H9a109.5
C5—C6—C1120.6 (2)N2—C9—H9b109.5
C1—N1—H1116.2H9a—C9—H9b109.5
O1—P1—N1—C168.3 (2)C6—C1—C2—C30.0 (4)
N2—P1—N1—C154.0 (2)N1—C1—C2—C3178.6 (2)
N1i—P1—N1—C1167.1 (1)C1—C2—C3—C40.3 (4)
O1—P1—N2—C8180.0C2—C3—C4—C50.0 (4)
N1—P1—N2—C853.1 (1)C2—C3—C4—C7178.0 (3)
N1i—P1—N2—C853.1 (1)C3—C4—C5—C60.6 (4)
O1—P1—N2—C90.0C7—C4—C5—C6178.7 (3)
N1—P1—N2—C9126.9 (1)C4—C5—C6—C10.9 (4)
N1i—P1—N2—C9126.9 (1)C2—C1—C6—C50.6 (4)
P1—N1—C1—C2177.5 (2)N1—C1—C6—C5177.9 (2)
P1—N1—C1—C61.0 (3)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.862.132.958 (3)163
Symmetry code: (ii) x+1/2, y+1/2, z.
 

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