N,N-Di­methyl-N′,N′′-bis(4-methyl­phenyl)­phospho­ramidate

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.

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

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Computing details

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

Crystal data

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) Å^3	T = 298 K
Z = 4	Block, colorless
F(000) = 648	0.42 × 0.21 × 0.10 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.156	w = 1/[σ^2(Fo^2) + (0.0811P)^2 + 0.2692P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—N1^i	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—N1^i	116.1 (1)	C3—C2—H2	119.6
O1—P1—N2	108.3 (1)	C1—C2—H2	119.6
N1—P1—N1^i	98.4 (2)	C2—C3—H3	119.0
N1—P1—N2	108.7 (1)	C4—C3—H3	119.0
N1^i—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)
N1^i—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)
N1^i—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)
N1^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^ii	0.86	2.13	2.958 (3)	163

Symmetry code: (ii) x+1/2, −y+1/2, z.