N,N'-Dibenzyl-N''-(2,6-difluoro-benzo-yl)-N,N'-dimethyl-phospho-ric triamide.

The phosphoryl and carbonyl groups in the title compound, C(23)H(24)F(2)N(3)O(2)P, are anti to each other. The P atom is in a tetra-hedral coordination environment and the environment of each N atom is essentially planar, the average bond angles at the two N atoms being 119.9 and 119.1°. The H atom of the C(=O)NHP(=O) group is involved in an inter-molecular -P=O⋯H-N- hydrogen bond, forming centrosymmetric dimers.

Related literature

For related structures, see: Pourayoubi & Sabbaghi (2009 ▶); Sabbaghi et al. (2010 ▶).

Experimental

Crystal data

C23H24F2N3O2P

M = 443.42

Triclinic,

a = 9.9370 (11) Å

b = 11.1093 (15) Å

c = 11.5902 (14) Å

α = 89.101 (4)°

β = 67.826 (4)°

γ = 71.664 (4)°

V = 1116.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 200 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART X2S benchtop CCD area-detector diffractometer

Absorption correction: multi-scan SADABS (Bruker, 2005 ▶) T min = 0.952, T max = 0.968

13602 measured reflections

5173 independent reflections

3851 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.126

S = 1.03

5173 reflections

286 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035725/ng5027sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035725/ng5027Isup2.hkl

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

C23H24F2N3O2P	Z = 2
Mr = 443.42	F(000) = 464
Triclinic, P1	Dx = 1.318 Mg m−3
a = 9.9370 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1093 (15) Å	Cell parameters from 5531 reflections
c = 11.5902 (14) Å	θ = 2.4–27.8°
α = 89.101 (4)°	µ = 0.16 mm−1
β = 67.826 (4)°	T = 200 K
γ = 71.664 (4)°	BLOCK, colorless
V = 1116.9 (2) Å3	0.30 × 0.25 × 0.20 mm

Bruker SMART X2S benchtop CCD area-detector diffractometer	5173 independent reflections
Radiation source: fine-focus sealed tube	3851 reflections with I > 2σ(I)
curved silicon crystal	Rint = 0.036
phi and ω scans	θmax = 27.8°, θmin = 2.4°
Absorption correction: multi-scan SADABS (Bruker, 2005)	h = −13→13
Tmin = 0.952, Tmax = 0.968	k = −14→14
13602 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.2218P] where P = (Fo2 + 2Fc2)/3
5173 reflections	(Δ/σ)max = 0.001
286 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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
P1	0.66485 (5)	0.42270 (4)	0.29906 (4)	0.02461 (13)
F1	0.41237 (17)	0.18210 (16)	0.50507 (15)	0.0723 (5)
F2	0.16095 (14)	0.43844 (12)	0.27352 (13)	0.0532 (4)
O1	0.50833 (16)	0.27969 (15)	0.19272 (13)	0.0445 (4)
O2	0.68882 (13)	0.46617 (12)	0.40757 (12)	0.0323 (3)
N1	0.48905 (16)	0.40601 (15)	0.35526 (15)	0.0277 (3)
N2	0.79630 (15)	0.28474 (13)	0.22927 (13)	0.0246 (3)
N3	0.66719 (17)	0.52094 (15)	0.19333 (15)	0.0358 (4)
C1	0.2810 (2)	0.2390 (2)	0.4858 (2)	0.0449 (5)
C2	0.1464 (3)	0.2189 (3)	0.5632 (2)	0.0583 (7)
H2A	0.1443	0.1678	0.6299	0.070*
C3	0.0152 (3)	0.2755 (3)	0.5402 (2)	0.0573 (7)
H3A	−0.0785	0.2634	0.5924	0.069*
C4	0.0174 (2)	0.3490 (2)	0.4434 (2)	0.0485 (6)
H4A	−0.0733	0.3880	0.4282	0.058*
C5	0.1560 (2)	0.3646 (2)	0.36861 (19)	0.0370 (5)
C6	0.2916 (2)	0.31110 (18)	0.38644 (17)	0.0315 (4)
C7	0.4403 (2)	0.32953 (18)	0.30107 (17)	0.0309 (4)
C8	0.86123 (19)	0.24379 (17)	0.09447 (16)	0.0280 (4)
H8A	0.8268	0.3173	0.0509	0.034*
H8B	0.8212	0.1771	0.0792	0.034*
C9	1.03733 (19)	0.19106 (16)	0.03916 (16)	0.0250 (4)
C10	1.1236 (2)	0.22336 (17)	0.09620 (17)	0.0296 (4)
H10A	1.0727	0.2797	0.1720	0.035*
C11	1.2842 (2)	0.17395 (19)	0.04339 (18)	0.0341 (4)
H11A	1.3419	0.1964	0.0836	0.041*
C12	1.3599 (2)	0.09219 (18)	−0.06744 (19)	0.0358 (5)
H12A	1.4693	0.0584	−0.1033	0.043*
C13	1.2756 (2)	0.06030 (19)	−0.12524 (19)	0.0393 (5)
H13A	1.3270	0.0049	−0.2017	0.047*
C14	1.1147 (2)	0.10908 (18)	−0.07202 (18)	0.0336 (4)
H14A	1.0575	0.0859	−0.1123	0.040*
C15	0.8149 (2)	0.18153 (18)	0.30902 (18)	0.0351 (4)
H15A	0.9229	0.1261	0.2767	0.053*
H15B	0.7497	0.1313	0.3084	0.053*
H15C	0.7842	0.2184	0.3951	0.053*
C16	0.5493 (2)	0.56887 (19)	0.14191 (18)	0.0382 (5)
H16A	0.4917	0.5083	0.1535	0.046*
H16B	0.6010	0.5705	0.0506	0.046*
C17	0.4345 (2)	0.70157 (17)	0.20021 (17)	0.0290 (4)
C18	0.3442 (2)	0.76890 (19)	0.13718 (19)	0.0360 (5)
H18A	0.3538	0.7308	0.0604	0.043*
C19	0.2409 (2)	0.8908 (2)	0.1858 (2)	0.0402 (5)
H19A	0.1796	0.9355	0.1426	0.048*
C20	0.2266 (2)	0.9478 (2)	0.2971 (2)	0.0414 (5)
H20A	0.1568	1.0319	0.3297	0.050*
C21	0.3144 (2)	0.88166 (19)	0.36020 (18)	0.0399 (5)
H21A	0.3047	0.9202	0.4368	0.048*
C22	0.4176 (2)	0.75831 (18)	0.31215 (18)	0.0344 (4)
H22A	0.4767	0.7130	0.3569	0.041*
C23	0.7939 (3)	0.5743 (2)	0.1510 (3)	0.0603 (7)
H23A	0.8498	0.5537	0.0599	0.091*
H23B	0.8646	0.5376	0.1925	0.091*
H23C	0.7516	0.6673	0.1724	0.091*
H1A	0.429 (2)	0.442 (2)	0.427 (2)	0.038 (6)*

	U11	U22	U33	U12	U13	U23
P1	0.0173 (2)	0.0247 (2)	0.0261 (2)	−0.00350 (17)	−0.00496 (17)	−0.00334 (17)
F1	0.0611 (9)	0.0976 (12)	0.0788 (11)	−0.0319 (9)	−0.0460 (8)	0.0389 (9)
F2	0.0449 (7)	0.0539 (8)	0.0632 (9)	−0.0087 (6)	−0.0301 (7)	0.0035 (7)
O1	0.0354 (8)	0.0614 (10)	0.0329 (8)	−0.0183 (7)	−0.0068 (6)	−0.0151 (7)
O2	0.0208 (6)	0.0398 (7)	0.0315 (7)	−0.0084 (5)	−0.0061 (5)	−0.0112 (6)
N1	0.0182 (7)	0.0342 (8)	0.0262 (8)	−0.0076 (6)	−0.0044 (6)	−0.0074 (7)
N2	0.0206 (7)	0.0242 (7)	0.0231 (7)	−0.0022 (6)	−0.0064 (6)	0.0009 (6)
N3	0.0259 (8)	0.0294 (8)	0.0446 (10)	−0.0035 (7)	−0.0107 (7)	0.0096 (7)
C1	0.0398 (12)	0.0603 (14)	0.0426 (12)	−0.0222 (11)	−0.0200 (10)	0.0059 (11)
C2	0.0607 (16)	0.0738 (18)	0.0467 (14)	−0.0402 (14)	−0.0133 (12)	0.0104 (13)
C3	0.0415 (13)	0.0695 (17)	0.0565 (15)	−0.0329 (13)	−0.0022 (11)	−0.0100 (13)
C4	0.0249 (10)	0.0540 (14)	0.0626 (15)	−0.0107 (10)	−0.0140 (10)	−0.0199 (12)
C5	0.0305 (10)	0.0391 (11)	0.0407 (11)	−0.0086 (8)	−0.0152 (9)	−0.0073 (9)
C6	0.0242 (9)	0.0382 (10)	0.0320 (10)	−0.0110 (8)	−0.0100 (8)	−0.0080 (8)
C7	0.0229 (9)	0.0361 (10)	0.0314 (10)	−0.0061 (8)	−0.0110 (8)	−0.0053 (8)
C8	0.0242 (9)	0.0297 (9)	0.0241 (9)	−0.0045 (7)	−0.0065 (7)	−0.0026 (7)
C9	0.0220 (8)	0.0247 (9)	0.0249 (9)	−0.0068 (7)	−0.0062 (7)	0.0030 (7)
C10	0.0291 (9)	0.0305 (9)	0.0268 (9)	−0.0079 (8)	−0.0100 (8)	0.0001 (7)
C11	0.0277 (10)	0.0394 (11)	0.0377 (11)	−0.0139 (8)	−0.0135 (8)	0.0078 (9)
C12	0.0202 (9)	0.0349 (10)	0.0431 (11)	−0.0073 (8)	−0.0042 (8)	0.0062 (9)
C13	0.0289 (10)	0.0364 (11)	0.0366 (11)	−0.0061 (8)	0.0008 (8)	−0.0093 (9)
C14	0.0275 (9)	0.0347 (10)	0.0341 (10)	−0.0113 (8)	−0.0063 (8)	−0.0046 (8)
C15	0.0328 (10)	0.0314 (10)	0.0344 (10)	−0.0050 (8)	−0.0106 (8)	0.0058 (8)
C16	0.0437 (11)	0.0322 (10)	0.0317 (10)	−0.0024 (9)	−0.0158 (9)	0.0019 (8)
C17	0.0267 (9)	0.0288 (9)	0.0299 (9)	−0.0078 (7)	−0.0107 (8)	0.0061 (8)
C18	0.0359 (10)	0.0403 (11)	0.0377 (11)	−0.0136 (9)	−0.0202 (9)	0.0070 (9)
C19	0.0299 (10)	0.0413 (12)	0.0511 (13)	−0.0066 (9)	−0.0222 (9)	0.0147 (10)
C20	0.0324 (10)	0.0326 (11)	0.0463 (12)	−0.0009 (8)	−0.0100 (9)	0.0057 (9)
C21	0.0426 (12)	0.0362 (11)	0.0322 (11)	−0.0068 (9)	−0.0103 (9)	0.0014 (9)
C22	0.0364 (10)	0.0304 (10)	0.0323 (10)	−0.0030 (8)	−0.0158 (8)	0.0060 (8)
C23	0.0362 (12)	0.0495 (14)	0.0853 (19)	−0.0157 (11)	−0.0129 (12)	0.0317 (13)

P1—O2	1.4796 (13)	C10—H10A	0.9500
P1—N3	1.6266 (16)	C11—C12	1.385 (3)
P1—N2	1.6405 (14)	C11—H11A	0.9500
P1—N1	1.6886 (15)	C12—C13	1.377 (3)
F1—C1	1.360 (2)	C12—H12A	0.9500
F2—C5	1.359 (2)	C13—C14	1.397 (3)
O1—C7	1.219 (2)	C13—H13A	0.9500
N1—C7	1.362 (2)	C14—H14A	0.9500
N1—H1A	0.83 (2)	C15—H15A	0.9800
N2—C8	1.463 (2)	C15—H15B	0.9800
N2—C15	1.471 (2)	C15—H15C	0.9800
N3—C16	1.462 (2)	C16—C17	1.524 (3)
N3—C23	1.474 (3)	C16—H16A	0.9900
C1—C6	1.383 (3)	C16—H16B	0.9900
C1—C2	1.386 (3)	C17—C22	1.380 (3)
C2—C3	1.380 (4)	C17—C18	1.397 (3)
C2—H2A	0.9500	C18—C19	1.385 (3)
C3—C4	1.375 (3)	C18—H18A	0.9500
C3—H3A	0.9500	C19—C20	1.384 (3)
C4—C5	1.386 (3)	C19—H19A	0.9500
C4—H4A	0.9500	C20—C21	1.378 (3)
C5—C6	1.383 (3)	C20—H20A	0.9500
C6—C7	1.512 (3)	C21—C22	1.396 (3)
C8—C9	1.529 (2)	C21—H21A	0.9500
C8—H8A	0.9900	C22—H22A	0.9500
C8—H8B	0.9900	C23—H23A	0.9800
C9—C14	1.389 (2)	C23—H23B	0.9800
C9—C10	1.389 (2)	C23—H23C	0.9800
C10—C11	1.395 (2)
O2—P1—N3	114.81 (8)	C12—C11—C10	120.19 (18)
O2—P1—N2	110.54 (7)	C12—C11—H11A	119.9
N3—P1—N2	107.66 (8)	C10—C11—H11A	119.9
O2—P1—N1	107.11 (8)	C13—C12—C11	119.55 (17)
N3—P1—N1	107.24 (8)	C13—C12—H12A	120.2
N2—P1—N1	109.34 (8)	C11—C12—H12A	120.2
C7—N1—P1	126.79 (13)	C12—C13—C14	120.31 (18)
C7—N1—H1A	116.4 (14)	C12—C13—H13A	119.8
P1—N1—H1A	116.5 (14)	C14—C13—H13A	119.8
C8—N2—C15	115.44 (14)	C9—C14—C13	120.73 (18)
C8—N2—P1	125.15 (12)	C9—C14—H14A	119.6
C15—N2—P1	116.63 (11)	C13—C14—H14A	119.6
C16—N3—C23	116.19 (17)	N2—C15—H15A	109.5
C16—N3—P1	126.13 (14)	N2—C15—H15B	109.5
C23—N3—P1	117.53 (14)	H15A—C15—H15B	109.5
F1—C1—C6	117.31 (18)	N2—C15—H15C	109.5
F1—C1—C2	119.0 (2)	H15A—C15—H15C	109.5
C6—C1—C2	123.7 (2)	H15B—C15—H15C	109.5
C3—C2—C1	117.9 (2)	N3—C16—C17	114.79 (16)
C3—C2—H2A	121.1	N3—C16—H16A	108.6
C1—C2—H2A	121.1	C17—C16—H16A	108.6
C4—C3—C2	121.4 (2)	N3—C16—H16B	108.6
C4—C3—H3A	119.3	C17—C16—H16B	108.6
C2—C3—H3A	119.3	H16A—C16—H16B	107.5
C3—C4—C5	118.0 (2)	C22—C17—C18	118.77 (17)
C3—C4—H4A	121.0	C22—C17—C16	122.46 (16)
C5—C4—H4A	121.0	C18—C17—C16	118.76 (17)
F2—C5—C6	117.05 (18)	C19—C18—C17	120.47 (19)
F2—C5—C4	119.21 (19)	C19—C18—H18A	119.8
C6—C5—C4	123.7 (2)	C17—C18—H18A	119.8
C5—C6—C1	115.30 (18)	C20—C19—C18	120.37 (18)
C5—C6—C7	121.65 (18)	C20—C19—H19A	119.8
C1—C6—C7	123.04 (17)	C18—C19—H19A	119.8
O1—C7—N1	123.93 (17)	C21—C20—C19	119.48 (19)
O1—C7—C6	121.61 (16)	C21—C20—H20A	120.3
N1—C7—C6	114.46 (15)	C19—C20—H20A	120.3
N2—C8—C9	112.58 (14)	C20—C21—C22	120.33 (19)
N2—C8—H8A	109.1	C20—C21—H21A	119.8
C9—C8—H8A	109.1	C22—C21—H21A	119.8
N2—C8—H8B	109.1	C17—C22—C21	120.56 (18)
C9—C8—H8B	109.1	C17—C22—H22A	119.7
H8A—C8—H8B	107.8	C21—C22—H22A	119.7
C14—C9—C10	118.49 (16)	N3—C23—H23A	109.5
C14—C9—C8	119.50 (15)	N3—C23—H23B	109.5
C10—C9—C8	122.01 (15)	H23A—C23—H23B	109.5
C9—C10—C11	120.73 (17)	N3—C23—H23C	109.5
C9—C10—H10A	119.6	H23A—C23—H23C	109.5
C11—C10—H10A	119.6	H23B—C23—H23C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.83 (2)	1.92 (2)	2.752 (2)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.83 (2)	1.92 (2)	2.752 (2)	173 (2)

Symmetry code: (i) .