organic compounds
Adjacent molecules of the title compound [alternative name: phosphoric bis(4-methylbenzamide) dimethylamide], C16H22N3OP, with tetrahedral phosphorus, are linked by twin N—HO [NO = 2.958 (3) Å] hydrogen bonds into a linear chain.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001587/cf6140sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001587/cf6140Isup2.hkl |
CCDC reference: 180809
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
C16H22N3OP | Dx = 1.228 Mg m−3 |
Mr = 303.34 | Melting point = 164–166 K |
Orthorhombic, Pnam | Mo Kα radiation, λ = 0.71073 Å |
a = 9.305 (9) Å | Cell parameters from 25 reflections |
b = 10.101 (2) Å | θ = 12.9–18.3° |
c = 17.454 (2) Å | µ = 0.17 mm−1 |
V = 1641 (2) Å3 | T = 298 K |
Z = 4 | Block, colorless |
F(000) = 648 | 0.42 × 0.21 × 0.10 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 1213 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
ω–2θ scans | h = −12→0 |
Absorption correction: empirical ψ scan (North et al., 1968) | k = 0→13 |
Tmin = 0.881, Tmax = 0.968 | l = −22→0 |
1939 measured reflections | 3 standard reflections every 120 min |
1939 independent reflections | intensity decay: 1% |
Refinement top
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)] = 0.051 | H-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 reflections | Δρmax = 0.30 e Å−3 |
105 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.021 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
P1 | 0.23185 (8) | 0.36794 (8) | 0.2500 | 0.0451 (3) | |
O1 | 0.0868 (2) | 0.3082 (2) | 0.2500 | 0.0592 (7) | |
N1 | 0.3375 (2) | 0.3255 (2) | 0.3212 (1) | 0.0534 (5) | |
N2 | 0.2141 (3) | 0.5281 (3) | 0.2500 | 0.0605 (8) | |
C1 | 0.3225 (2) | 0.3585 (2) | 0.3993 (1) | 0.0477 (6) | |
C2 | 0.4263 (3) | 0.3175 (3) | 0.4507 (2) | 0.0597 (7) | |
C3 | 0.4169 (3) | 0.3503 (3) | 0.5272 (2) | 0.0676 (8) | |
C4 | 0.3046 (3) | 0.4256 (3) | 0.5559 (2) | 0.0596 (7) | |
C5 | 0.2028 (3) | 0.4661 (3) | 0.5040 (2) | 0.0637 (7) | |
C6 | 0.2095 (2) | 0.4333 (3) | 0.4274 (2) | 0.0631 (7) | |
C7 | 0.2961 (3) | 0.4655 (3) | 0.6389 (2) | 0.0821 (9) | |
C8 | 0.3393 (4) | 0.6144 (4) | 0.2500 | 0.104 (2) | |
C9 | 0.0769 (4) | 0.5973 (5) | 0.2500 | 0.088 (2) | |
H1 | 0.4106 | 0.2775 | 0.3096 | 0.064* | |
H2 | 0.5035 | 0.2672 | 0.4335 | 0.072* | |
H3 | 0.4880 | 0.3209 | 0.5606 | 0.081* | |
H5 | 0.1264 | 0.5175 | 0.5211 | 0.076* | |
H6 | 0.1375 | 0.4616 | 0.3943 | 0.076* | |
H7a | 0.3687 | 0.5304 | 0.6496 | 0.123* | |
H7b | 0.3111 | 0.3892 | 0.6706 | 0.123* | |
H7c | 0.2030 | 0.5023 | 0.6493 | 0.123* | |
H8a | 0.4251 | 0.5617 | 0.2500 | 0.156* | |
H8b | 0.3377 | 0.6693 | 0.2949 | 0.156* | |
H9a | 0.0000 | 0.5339 | 0.2500 | 0.131* | |
H9b | 0.0701 | 0.6518 | 0.2051 | 0.131* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0286 (4) | 0.0472 (5) | 0.0594 (6) | −0.0036 (3) | 0.000 | 0.000 |
O1 | 0.036 (1) | 0.067 (2) | 0.074 (2) | −0.018 (1) | 0.000 | 0.000 |
N1 | 0.040 (1) | 0.061 (1) | 0.059 (1) | 0.012 (1) | −0.002 (1) | −0.008 (1) |
N2 | 0.029 (1) | 0.049 (2) | 0.103 (3) | 0.002 (1) | 0.000 | 0.000 |
C1 | 0.036 (1) | 0.048 (1) | 0.059 (1) | −0.002 (1) | 0.003 (1) | −0.004 (1) |
C2 | 0.051 (1) | 0.062 (2) | 0.066 (2) | 0.014 (1) | 0.004 (1) | 0.004 (1) |
C3 | 0.061 (2) | 0.080 (2) | 0.062 (2) | 0.013 (1) | −0.004 (1) | 0.006 (1) |
C4 | 0.055 (2) | 0.065 (2) | 0.059 (2) | −0.011 (1) | 0.006 (1) | −0.002 (1) |
C5 | 0.044 (1) | 0.077 (2) | 0.070 (2) | 0.005 (1) | 0.007 (1) | −0.016 (2) |
C6 | 0.038 (1) | 0.084 (2) | 0.068 (2) | 0.010 (1) | −0.006 (1) | −0.010 (1) |
C7 | 0.084 (2) | 0.098 (2) | 0.064 (2) | −0.005 (2) | 0.009 (2) | −0.006 (2) |
C8 | 0.054 (2) | 0.056 (2) | 0.202 (6) | −0.012 (2) | 0.000 | 0.000 |
C9 | 0.046 (2) | 0.076 (3) | 0.141 (4) | 0.023 (2) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
P1—O1 | 1.478 (2) | C5—C6 | 1.379 (4) |
P1—N2 | 1.626 (3) | N1—H1 | 0.860 |
P1—N1 | 1.642 (2) | C2—H2 | 0.930 |
P1—N1i | 1.642 (2) | C3—H3 | 0.930 |
N1—C1 | 1.409 (3) | C5—H5 | 0.930 |
N2—C8 | 1.455 (5) | C6—H6 | 0.930 |
N2—C9 | 1.456 (4) | C7—H7a | 0.960 |
C1—C2 | 1.383 (3) | C7—H7b | 0.960 |
C1—C6 | 1.384 (3) | C7—H7c | 0.960 |
C2—C3 | 1.379 (4) | C8—H8a | 0.960 |
C3—C4 | 1.386 (4) | C8—H8b | 0.960 |
C4—C5 | 1.373 (4) | C9—H9a | 0.960 |
C4—C7 | 1.506 (4) | C9—H9b | 0.960 |
O1—P1—N1 | 116.1 (1) | P1—N1—H1 | 116.2 |
O1—P1—N1i | 116.1 (1) | C3—C2—H2 | 119.6 |
O1—P1—N2 | 108.3 (1) | C1—C2—H2 | 119.6 |
N1—P1—N1i | 98.4 (2) | C2—C3—H3 | 119.0 |
N1—P1—N2 | 108.7 (1) | C4—C3—H3 | 119.0 |
N1i—P1—N2 | 108.7 (1) | C4—C5—H5 | 118.8 |
C1—N1—P1 | 127.6 (2) | C6—C5—H5 | 118.8 |
C8—N2—C9 | 114.5 (3) | C5—C6—H6 | 119.7 |
C8—N2—P1 | 121.0 (2) | C1—C6—H6 | 119.7 |
C9—N2—P1 | 124.5 (3) | C4—C7—H7a | 109.5 |
C2—C1—C6 | 117.6 (3) | C4—C7—H7b | 109.5 |
C2—C1—N1 | 119.2 (2) | H7a—C7—H7b | 109.5 |
C6—C1—N1 | 123.2 (2) | C4—C7—H7c | 109.5 |
C3—C2—C1 | 120.9 (2) | H7a—C7—H7c | 109.5 |
C2—C3—C4 | 121.9 (3) | H7b—C7—H7c | 109.5 |
C5—C4—C3 | 116.4 (3) | N2—C8—H8a | 109.5 |
C5—C4—C7 | 121.2 (3) | N2—C8—H8b | 109.5 |
C3—C4—C7 | 122.3 (3) | H8a—C8—H8b | 109.5 |
C4—C5—C6 | 122.5 (2) | N2—C9—H9a | 109.5 |
C5—C6—C1 | 120.6 (2) | N2—C9—H9b | 109.5 |
C1—N1—H1 | 116.2 | H9a—C9—H9b | 109.5 |
O1—P1—N1—C1 | −68.3 (2) | C6—C1—C2—C3 | 0.0 (4) |
N2—P1—N1—C1 | 54.0 (2) | N1—C1—C2—C3 | 178.6 (2) |
N1i—P1—N1—C1 | 167.1 (1) | C1—C2—C3—C4 | −0.3 (4) |
O1—P1—N2—C8 | 180.0 | C2—C3—C4—C5 | 0.0 (4) |
N1—P1—N2—C8 | 53.1 (1) | C2—C3—C4—C7 | −178.0 (3) |
N1i—P1—N2—C8 | −53.1 (1) | C3—C4—C5—C6 | 0.6 (4) |
O1—P1—N2—C9 | 0.0 | C7—C4—C5—C6 | 178.7 (3) |
N1—P1—N2—C9 | −126.9 (1) | C4—C5—C6—C1 | −0.9 (4) |
N1i—P1—N2—C9 | 126.9 (1) | C2—C1—C6—C5 | 0.6 (4) |
P1—N1—C1—C2 | −177.5 (2) | N1—C1—C6—C5 | −177.9 (2) |
P1—N1—C1—C6 | 1.0 (3) |
Symmetry code: (i) x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.86 | 2.13 | 2.958 (3) | 163 |
Symmetry code: (ii) x+1/2, −y+1/2, z. |