N,N-Dimethyl-N',N''-diphenyl-phospho-ric triamide.

In the title compound, C(14)H(18)N(3)OP, a crystallographic mirror plane bis-ects the mol-ecule (the C,N,C atoms of the dimethyl-amido moiety and the P=O unit lie on the mirror plane). The P atom has a distorted tetra-hedral geometry; the bond angles at P are in the range 98.98 (11)-115.28 (7)°. In the crystal, the O atom of the P=O group acts as a double hydrogen-bond acceptor for two symmetry-equivalent N-H⋯O hydrogen bonds, building [001] chains containing R(2) (1)(6) loops.

Related literature

For bond lengths and angles in compounds having a [(N)P(O)(N)2] skeleton, see: Sabbaghi et al. (2011 ▶). For the double hydrogen-bond acceptor capability of the phosphoryl group, see: Pourayoubi et al. (2011 ▶).

Experimental

Crystal data

C14H18N3OP

M = 275.28

Orthorhombic,

a = 15.501 (3) Å

b = 10.8569 (17) Å

c = 8.1579 (13) Å

V = 1372.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.60 × 0.15 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.891, T max = 0.975

5356 measured reflections

1317 independent reflections

1272 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.084

S = 1.04

1317 reflections

108 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 604 Friedel pairs

Flack parameter: −0.11 (10)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811046058/hb6483sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046058/hb6483Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H18N3OP	Dx = 1.332 Mg m−3
Mr = 275.28	Melting point: NOT MEASURED K
Orthorhombic, Cmc21	Mo Kα radiation, λ = 0.71073 Å
a = 15.501 (3) Å	Cell parameters from 3006 reflections
b = 10.8569 (17) Å	θ = 3.4–25.5°
c = 8.1579 (13) Å	µ = 0.20 mm−1
V = 1372.9 (4) Å3	T = 100 K
Z = 4	Rod, colourless
F(000) = 584	0.60 × 0.15 × 0.13 mm

Bruker APEXII CCD diffractometer	1317 independent reflections
Radiation source: fine-focus sealed tube	1272 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −18→14
Tmin = 0.891, Tmax = 0.975	k = −13→11
5356 measured reflections	l = −9→9

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0623P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
1317 reflections	Δρmax = 0.22 e Å−3
108 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 604 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.11 (10)

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
H13	−0.0531 (17)	0.819 (2)	−0.158 (3)	0.043 (6)*
H11	0.0000	0.708 (4)	−0.186 (5)	0.052 (11)*
H12	0.0000	0.849 (4)	0.262 (6)	0.053 (11)*
H4	−0.0525 (13)	0.9247 (19)	0.112 (3)	0.028 (5)*
P1	0.0000	0.62183 (5)	0.12667 (6)	0.02090 (19)
O1	0.0000	0.63022 (15)	0.3089 (2)	0.0251 (4)
N1	0.08103 (10)	0.54350 (14)	0.0464 (2)	0.0254 (4)
H1A	0.0696	0.4706	0.0047	0.031*
N2	0.0000	0.76094 (19)	0.0485 (3)	0.0243 (5)
C1	0.34009 (13)	0.66067 (19)	0.0212 (2)	0.0271 (4)
H1	0.3986	0.6864	0.0142	0.033*
C2	0.31200 (13)	0.55744 (18)	−0.0645 (2)	0.0283 (4)
H2	0.3515	0.5125	−0.1303	0.034*
C3	0.22643 (11)	0.51958 (17)	−0.0546 (2)	0.0243 (4)
H3	0.2080	0.4485	−0.1128	0.029*
C4	0.16777 (13)	0.58505 (18)	0.0398 (2)	0.0232 (4)
C5	0.28212 (11)	0.72536 (16)	0.1165 (3)	0.0252 (4)
H5	0.3011	0.7954	0.1762	0.030*
C6	0.19609 (10)	0.68909 (16)	0.1260 (3)	0.0241 (4)
H6	0.1566	0.7349	0.1910	0.029*
C7	0.0000	0.8737 (2)	0.1449 (4)	0.0269 (6)
C8	0.0000	0.7773 (3)	−0.1284 (4)	0.0329 (6)

	U11	U22	U33	U12	U13	U23
P1	0.0224 (3)	0.0191 (3)	0.0212 (3)	0.000	0.000	0.0002 (3)
O1	0.0304 (10)	0.0227 (9)	0.0221 (10)	0.000	0.000	0.0036 (7)
N1	0.0246 (8)	0.0218 (8)	0.0300 (8)	−0.0009 (6)	0.0010 (6)	−0.0034 (6)
N2	0.0304 (11)	0.0218 (11)	0.0208 (12)	0.000	0.000	−0.0001 (8)
C1	0.0239 (9)	0.0308 (10)	0.0265 (9)	0.0005 (8)	−0.0006 (8)	0.0058 (8)
C2	0.0286 (9)	0.0314 (10)	0.0248 (9)	0.0073 (8)	0.0025 (8)	0.0006 (8)
C3	0.0289 (9)	0.0215 (9)	0.0225 (9)	0.0025 (7)	−0.0021 (8)	0.0006 (7)
C4	0.0264 (9)	0.0208 (10)	0.0224 (10)	0.0021 (8)	−0.0024 (7)	0.0032 (7)
C5	0.0296 (8)	0.0230 (8)	0.0230 (9)	0.0005 (7)	−0.0033 (9)	0.0038 (8)
C6	0.0269 (8)	0.0226 (8)	0.0227 (7)	0.0043 (7)	0.0013 (8)	−0.0007 (8)
C7	0.0342 (13)	0.0224 (13)	0.0241 (14)	0.000	0.000	0.0001 (10)
C8	0.0446 (17)	0.0310 (16)	0.0232 (14)	0.000	0.000	0.0029 (12)

P1—O1	1.489 (2)	C2—H2	0.9500
P1—N2	1.639 (2)	C3—C4	1.388 (3)
P1—N1i	1.6521 (16)	C3—H3	0.9500
P1—N1	1.6522 (16)	C4—C6	1.401 (3)
N1—C4	1.419 (2)	C5—C6	1.393 (2)
N1—H1A	0.8800	C5—H5	0.9500
N2—C8	1.454 (3)	C6—H6	0.9500
N2—C7	1.455 (3)	C7—H12	0.99 (5)
C1—C5	1.380 (3)	C7—H4	1.02 (2)
C1—C2	1.391 (3)	C8—H13	0.97 (3)
C1—H1	0.9500	C8—H11	0.89 (4)
C2—C3	1.391 (3)
O1—P1—N2	109.39 (11)	C4—C3—C2	120.39 (18)
O1—P1—N1i	115.28 (7)	C4—C3—H3	119.8
N2—P1—N1i	108.66 (8)	C2—C3—H3	119.8
O1—P1—N1	115.28 (7)	C3—C4—C6	119.10 (17)
N2—P1—N1	108.66 (8)	C3—C4—N1	118.62 (16)
N1i—P1—N1	98.98 (11)	C6—C4—N1	122.28 (16)
C4—N1—P1	124.87 (13)	C1—C5—C6	120.74 (18)
C4—N1—H1A	117.6	C1—C5—H5	119.6
P1—N1—H1A	117.6	C6—C5—H5	119.6
C8—N2—C7	115.7 (2)	C5—C6—C4	119.99 (17)
C8—N2—P1	119.9 (2)	C5—C6—H6	120.0
C7—N2—P1	124.38 (19)	C4—C6—H6	120.0
C5—C1—C2	119.30 (18)	N2—C7—H12	107 (2)
C5—C1—H1	120.4	N2—C7—H4	108.2 (13)
C2—C1—H1	120.4	H12—C7—H4	113.7 (18)
C1—C2—C3	120.49 (18)	N2—C8—H13	107.6 (15)
C1—C2—H2	119.8	N2—C8—H11	115 (3)
C3—C2—H2	119.8	H13—C8—H11	105.1 (19)
O1—P1—N1—C4	−72.29 (16)	C1—C2—C3—C4	0.6 (3)
N2—P1—N1—C4	50.87 (18)	C2—C3—C4—C6	−0.5 (3)
N1i—P1—N1—C4	164.16 (11)	C2—C3—C4—N1	179.88 (17)
O1—P1—N2—C8	180.0	P1—N1—C4—C3	−169.43 (13)
N1i—P1—N2—C8	−53.37 (7)	P1—N1—C4—C6	11.0 (2)
N1—P1—N2—C8	53.37 (7)	C2—C1—C5—C6	−0.7 (3)
O1—P1—N2—C7	0.0	C1—C5—C6—C4	0.7 (3)
N1i—P1—N2—C7	126.63 (7)	C3—C4—C6—C5	−0.1 (3)
N1—P1—N2—C7	−126.63 (7)	N1—C4—C6—C5	179.45 (18)
C5—C1—C2—C3	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.88	2.22	2.982 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.88	2.22	2.982 (2)	145

Symmetry code: (i) .