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

In the title mol-ecule, C(21)H(32)F(2)N(3)O(2)P, the P=O and N-H groups are syn with respect to each other, and the P atom is bonded in a distorted tetra-hedral environment. The phosphoryl group adopts an anti orientation with respect to the carbonyl group. The angles at the tertiary N atoms (with bond-angle sums of 358.4 and 357.0°) confirm their sp(2) character. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For hydrogen-bond patterns in compounds containing a C(O)NHP(O) skeleton, see: Toghraee et al. (2011 ▶); Pourayoubi et al. (2011 ▶). For background to phospho­ric triamide compounds containing a C(O)NHP(O) skeleton, and related bond lengths, angles and torsion angles, see: Pourayoubi et al. (2010 ▶); Amirkhanov et al. (2010 ▶); Tarahhomi et al. (2011 ▶). For a description of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H32F2N3O2P

M = 427.47

Triclinic,

a = 10.2322 (6) Å

b = 10.6188 (5) Å

c = 11.2658 (6) Å

α = 69.419 (1)°

β = 79.269 (1)°

γ = 81.536 (1)°

V = 1121.45 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.946, T max = 0.961

17147 measured reflections

5053 independent reflections

4421 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.05

5053 reflections

267 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.34 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 and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043029/bh2384sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043029/bh2384Isup2.hkl

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

C21H32F2N3O2P	Z = 2
Mr = 427.47	F(000) = 456
Triclinic, P1	Dx = 1.266 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2322 (6) Å	Cell parameters from 9954 reflections
b = 10.6188 (5) Å	θ = 2.4–28.0°
c = 11.2658 (6) Å	µ = 0.16 mm−1
α = 69.419 (1)°	T = 100 K
β = 79.269 (1)°	Block, colourless
γ = 81.536 (1)°	0.35 × 0.30 × 0.25 mm
V = 1121.45 (10) Å3

Bruker SMART CCD area-detector diffractometer	5053 independent reflections
Radiation source: fine-focus sealed tube	4421 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.946, Tmax = 0.961	k = −13→13
17147 measured reflections	l = −14→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.4607P] where P = (Fo2 + 2Fc2)/3
5053 reflections	(Δ/σ)max < 0.001
267 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.34 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
P1	0.42370 (3)	0.41644 (3)	0.20824 (3)	0.01482 (9)
F1	0.91928 (9)	0.33633 (12)	0.27902 (10)	0.0491 (3)
F2	0.68054 (9)	0.73518 (9)	0.04970 (9)	0.0363 (2)
O1	0.64907 (10)	0.41510 (13)	0.35266 (9)	0.0347 (3)
O2	0.35023 (8)	0.47928 (9)	0.09668 (8)	0.01753 (19)
N1	0.57558 (10)	0.47579 (11)	0.15972 (10)	0.0170 (2)
H1N	0.5985 (14)	0.5054 (14)	0.0781 (9)	0.020*
N2	0.34278 (10)	0.45423 (10)	0.33252 (9)	0.0165 (2)
N3	0.45145 (11)	0.25173 (11)	0.25782 (11)	0.0244 (2)
C1	0.91678 (14)	0.4643 (2)	0.19652 (16)	0.0392 (4)
C2	1.03613 (16)	0.5176 (3)	0.14059 (19)	0.0497 (5)
H2	1.1182	0.4669	0.1619	0.060*
C3	1.03445 (16)	0.6460 (3)	0.0529 (2)	0.0546 (6)
H3	1.1166	0.6842	0.0137	0.066*
C4	0.91532 (17)	0.7212 (2)	0.02025 (17)	0.0463 (5)
H4	0.9148	0.8099	−0.0405	0.056*
C5	0.79751 (14)	0.66235 (18)	0.07925 (15)	0.0333 (4)
C6	0.79311 (13)	0.53390 (17)	0.16838 (13)	0.0283 (3)
C7	0.66617 (13)	0.46961 (15)	0.23652 (13)	0.0236 (3)
C8	0.27329 (12)	0.59130 (12)	0.31148 (11)	0.0169 (2)
H8	0.2504	0.6255	0.2224	0.020*
C9	0.36202 (14)	0.69035 (14)	0.32103 (14)	0.0258 (3)
H9A	0.3890	0.6578	0.4075	0.031*
H9B	0.4439	0.6951	0.2575	0.031*
C10	0.28793 (18)	0.83088 (16)	0.29625 (17)	0.0388 (4)
H10A	0.3451	0.8918	0.3081	0.047*
H10B	0.2701	0.8673	0.2064	0.047*
C11	0.15626 (17)	0.82817 (16)	0.38598 (17)	0.0385 (4)
H11A	0.1743	0.8016	0.4753	0.046*
H11B	0.1085	0.9197	0.3635	0.046*
C12	0.06889 (15)	0.72885 (15)	0.37619 (16)	0.0328 (3)
H12A	0.0434	0.7605	0.2892	0.039*
H12B	−0.0139	0.7250	0.4385	0.039*
C13	0.14254 (13)	0.58770 (14)	0.40322 (13)	0.0222 (3)
H13A	0.1616	0.5529	0.4927	0.027*
H13B	0.0852	0.5257	0.3933	0.027*
C14	0.36037 (14)	0.37310 (14)	0.46557 (12)	0.0248 (3)
H14A	0.3893	0.4297	0.5066	0.037*
H14B	0.4281	0.2975	0.4658	0.037*
H14C	0.2754	0.3381	0.5129	0.037*
C15	0.57908 (14)	0.17673 (14)	0.22547 (14)	0.0277 (3)
H15	0.6473	0.2439	0.1874	0.033*
C16	0.57337 (16)	0.11177 (15)	0.12540 (14)	0.0335 (3)
H16A	0.5479	0.1824	0.0465	0.040*
H16B	0.5042	0.0468	0.1585	0.040*
C17	0.70838 (18)	0.03820 (16)	0.09313 (15)	0.0400 (4)
H17A	0.6998	−0.0088	0.0334	0.048*
H17B	0.7750	0.1049	0.0497	0.048*
C18	0.7570 (2)	−0.06431 (18)	0.21368 (16)	0.0476 (5)
H18A	0.6957	−0.1369	0.2517	0.057*
H18B	0.8468	−0.1059	0.1906	0.057*
C19	0.76312 (19)	0.00220 (19)	0.31179 (17)	0.0465 (5)
H19A	0.8303	0.0692	0.2766	0.056*
H19B	0.7914	−0.0671	0.3901	0.056*
C20	0.62703 (17)	0.07244 (16)	0.34615 (15)	0.0362 (4)
H20A	0.6341	0.1178	0.4076	0.043*
H20B	0.5613	0.0045	0.3877	0.043*
C21	0.33158 (15)	0.17706 (14)	0.30012 (15)	0.0304 (3)
H21A	0.3101	0.1560	0.2283	0.046*
H21B	0.2564	0.2325	0.3300	0.046*
H21C	0.3483	0.0930	0.3702	0.046*

	U11	U22	U33	U12	U13	U23
P1	0.01077 (15)	0.01879 (16)	0.01385 (15)	0.00019 (11)	−0.00010 (11)	−0.00559 (12)
F1	0.0221 (5)	0.0863 (8)	0.0401 (6)	0.0158 (5)	−0.0113 (4)	−0.0274 (6)
F2	0.0281 (5)	0.0433 (5)	0.0395 (5)	−0.0109 (4)	0.0008 (4)	−0.0161 (4)
O1	0.0187 (5)	0.0684 (8)	0.0170 (5)	0.0035 (5)	−0.0043 (4)	−0.0164 (5)
O2	0.0119 (4)	0.0264 (5)	0.0154 (4)	−0.0013 (3)	−0.0006 (3)	−0.0092 (4)
N1	0.0116 (5)	0.0268 (5)	0.0126 (5)	−0.0012 (4)	−0.0006 (4)	−0.0074 (4)
N2	0.0140 (5)	0.0206 (5)	0.0124 (5)	0.0026 (4)	−0.0013 (4)	−0.0044 (4)
N3	0.0186 (6)	0.0198 (5)	0.0281 (6)	0.0026 (4)	0.0060 (5)	−0.0061 (5)
C1	0.0152 (7)	0.0836 (13)	0.0351 (8)	0.0013 (7)	−0.0044 (6)	−0.0418 (9)
C2	0.0152 (7)	0.1089 (17)	0.0493 (11)	−0.0083 (9)	0.0001 (7)	−0.0576 (12)
C3	0.0188 (8)	0.1161 (19)	0.0591 (12)	−0.0293 (10)	0.0157 (8)	−0.0679 (13)
C4	0.0354 (9)	0.0766 (13)	0.0434 (10)	−0.0298 (9)	0.0141 (7)	−0.0405 (10)
C5	0.0183 (7)	0.0595 (10)	0.0340 (8)	−0.0111 (7)	0.0033 (6)	−0.0307 (8)
C6	0.0125 (6)	0.0588 (10)	0.0244 (7)	−0.0046 (6)	−0.0005 (5)	−0.0274 (7)
C7	0.0127 (6)	0.0419 (8)	0.0202 (6)	0.0028 (5)	−0.0026 (5)	−0.0170 (6)
C8	0.0153 (6)	0.0198 (6)	0.0155 (6)	0.0015 (5)	−0.0024 (4)	−0.0070 (5)
C9	0.0236 (7)	0.0311 (7)	0.0262 (7)	−0.0076 (6)	0.0032 (5)	−0.0154 (6)
C10	0.0485 (10)	0.0270 (8)	0.0419 (9)	−0.0089 (7)	0.0094 (8)	−0.0186 (7)
C11	0.0439 (10)	0.0299 (8)	0.0419 (9)	0.0036 (7)	0.0046 (7)	−0.0202 (7)
C12	0.0257 (8)	0.0348 (8)	0.0367 (8)	0.0103 (6)	−0.0032 (6)	−0.0163 (7)
C13	0.0143 (6)	0.0279 (7)	0.0246 (7)	0.0012 (5)	0.0004 (5)	−0.0120 (5)
C14	0.0206 (7)	0.0320 (7)	0.0141 (6)	0.0053 (5)	−0.0007 (5)	−0.0023 (5)
C15	0.0244 (7)	0.0221 (7)	0.0261 (7)	0.0086 (5)	0.0052 (6)	−0.0041 (5)
C16	0.0380 (9)	0.0265 (7)	0.0252 (7)	0.0099 (6)	0.0039 (6)	−0.0049 (6)
C17	0.0461 (10)	0.0314 (8)	0.0272 (8)	0.0161 (7)	0.0073 (7)	−0.0051 (6)
C18	0.0545 (12)	0.0374 (9)	0.0338 (9)	0.0271 (8)	0.0017 (8)	−0.0075 (7)
C19	0.0461 (11)	0.0447 (10)	0.0351 (9)	0.0269 (8)	−0.0058 (8)	−0.0087 (7)
C20	0.0383 (9)	0.0343 (8)	0.0266 (8)	0.0154 (7)	−0.0009 (7)	−0.0080 (6)
C21	0.0281 (8)	0.0204 (7)	0.0364 (8)	−0.0035 (5)	0.0085 (6)	−0.0078 (6)

P1—O2	1.4848 (9)	C11—C12	1.523 (2)
P1—N2	1.6348 (11)	C11—H11A	0.9900
P1—N3	1.6363 (11)	C11—H11B	0.9900
P1—N1	1.6854 (10)	C12—C13	1.5295 (19)
F1—C1	1.350 (2)	C12—H12A	0.9900
F2—C5	1.3552 (19)	C12—H12B	0.9900
O1—C7	1.2205 (16)	C13—H13A	0.9900
N1—C7	1.3612 (15)	C13—H13B	0.9900
N1—H1N	0.859 (9)	C14—H14A	0.9800
N2—C14	1.4725 (15)	C14—H14B	0.9800
N2—C8	1.4819 (15)	C14—H14C	0.9800
N3—C21	1.4707 (17)	C15—C16	1.528 (2)
N3—C15	1.4810 (17)	C15—C20	1.5314 (19)
C1—C2	1.369 (2)	C15—H15	1.0000
C1—C6	1.399 (2)	C16—C17	1.532 (2)
C2—C3	1.374 (3)	C16—H16A	0.9900
C2—H2	0.9500	C16—H16B	0.9900
C3—C4	1.390 (3)	C17—C18	1.526 (2)
C3—H3	0.9500	C17—H17A	0.9900
C4—C5	1.384 (2)	C17—H17B	0.9900
C4—H4	0.9500	C18—C19	1.521 (3)
C5—C6	1.382 (2)	C18—H18A	0.9900
C6—C7	1.5046 (18)	C18—H18B	0.9900
C8—C13	1.5271 (17)	C19—C20	1.530 (2)
C8—C9	1.5294 (17)	C19—H19A	0.9900
C8—H8	1.0000	C19—H19B	0.9900
C9—C10	1.527 (2)	C20—H20A	0.9900
C9—H9A	0.9900	C20—H20B	0.9900
C9—H9B	0.9900	C21—H21A	0.9800
C10—C11	1.524 (2)	C21—H21B	0.9800
C10—H10A	0.9900	C21—H21C	0.9800
C10—H10B	0.9900
O2—P1—N2	110.40 (5)	C11—C12—C13	110.95 (12)
O2—P1—N3	116.97 (6)	C11—C12—H12A	109.5
N2—P1—N3	105.60 (6)	C13—C12—H12A	109.5
O2—P1—N1	105.57 (5)	C11—C12—H12B	109.5
N2—P1—N1	112.66 (5)	C13—C12—H12B	109.5
N3—P1—N1	105.73 (6)	H12A—C12—H12B	108.0
C7—N1—P1	126.27 (9)	C8—C13—C12	110.68 (11)
C7—N1—H1N	118.7 (10)	C8—C13—H13A	109.5
P1—N1—H1N	114.7 (10)	C12—C13—H13A	109.5
C14—N2—C8	116.58 (10)	C8—C13—H13B	109.5
C14—N2—P1	123.33 (9)	C12—C13—H13B	109.5
C8—N2—P1	118.49 (8)	H13A—C13—H13B	108.1
C21—N3—C15	116.90 (11)	N2—C14—H14A	109.5
C21—N3—P1	115.51 (9)	N2—C14—H14B	109.5
C15—N3—P1	124.57 (9)	H14A—C14—H14B	109.5
F1—C1—C2	118.10 (16)	N2—C14—H14C	109.5
F1—C1—C6	118.56 (14)	H14A—C14—H14C	109.5
C2—C1—C6	123.28 (19)	H14B—C14—H14C	109.5
C1—C2—C3	118.40 (17)	N3—C15—C16	113.22 (12)
C1—C2—H2	120.8	N3—C15—C20	111.07 (11)
C3—C2—H2	120.8	C16—C15—C20	111.21 (12)
C2—C3—C4	121.52 (15)	N3—C15—H15	107.0
C2—C3—H3	119.2	C16—C15—H15	107.0
C4—C3—H3	119.2	C20—C15—H15	107.0
C5—C4—C3	117.7 (2)	C15—C16—C17	111.21 (14)
C5—C4—H4	121.1	C15—C16—H16A	109.4
C3—C4—H4	121.1	C17—C16—H16A	109.4
F2—C5—C6	118.33 (12)	C15—C16—H16B	109.4
F2—C5—C4	118.37 (17)	C17—C16—H16B	109.4
C6—C5—C4	123.29 (16)	H16A—C16—H16B	108.0
C5—C6—C1	115.79 (14)	C18—C17—C16	111.24 (13)
C5—C6—C7	124.16 (13)	C18—C17—H17A	109.4
C1—C6—C7	120.02 (15)	C16—C17—H17A	109.4
O1—C7—N1	123.71 (12)	C18—C17—H17B	109.4
O1—C7—C6	120.91 (11)	C16—C17—H17B	109.4
N1—C7—C6	115.38 (11)	H17A—C17—H17B	108.0
N2—C8—C13	111.30 (10)	C19—C18—C17	111.16 (14)
N2—C8—C9	112.22 (10)	C19—C18—H18A	109.4
C13—C8—C9	110.75 (10)	C17—C18—H18A	109.4
N2—C8—H8	107.4	C19—C18—H18B	109.4
C13—C8—H8	107.4	C17—C18—H18B	109.4
C9—C8—H8	107.4	H18A—C18—H18B	108.0
C10—C9—C8	110.65 (12)	C18—C19—C20	110.98 (16)
C10—C9—H9A	109.5	C18—C19—H19A	109.4
C8—C9—H9A	109.5	C20—C19—H19A	109.4
C10—C9—H9B	109.5	C18—C19—H19B	109.4
C8—C9—H9B	109.5	C20—C19—H19B	109.4
H9A—C9—H9B	108.1	H19A—C19—H19B	108.0
C11—C10—C9	111.80 (13)	C19—C20—C15	110.31 (12)
C11—C10—H10A	109.3	C19—C20—H20A	109.6
C9—C10—H10A	109.3	C15—C20—H20A	109.6
C11—C10—H10B	109.3	C19—C20—H20B	109.6
C9—C10—H10B	109.3	C15—C20—H20B	109.6
H10A—C10—H10B	107.9	H20A—C20—H20B	108.1
C12—C11—C10	110.74 (13)	N3—C21—H21A	109.5
C12—C11—H11A	109.5	N3—C21—H21B	109.5
C10—C11—H11A	109.5	H21A—C21—H21B	109.5
C12—C11—H11B	109.5	N3—C21—H21C	109.5
C10—C11—H11B	109.5	H21A—C21—H21C	109.5
H11A—C11—H11B	108.1	H21B—C21—H21C	109.5
O2—P1—N1—C7	164.83 (11)	P1—N1—C7—C6	−178.43 (10)
N2—P1—N1—C7	44.27 (13)	C5—C6—C7—O1	−131.18 (15)
N3—P1—N1—C7	−70.59 (12)	C1—C6—C7—O1	47.0 (2)
O2—P1—N2—C14	157.51 (10)	C5—C6—C7—N1	49.58 (19)
N3—P1—N2—C14	30.20 (11)	C1—C6—C7—N1	−132.22 (14)
N1—P1—N2—C14	−84.74 (11)	C14—N2—C8—C13	−50.03 (14)
O2—P1—N2—C8	−37.41 (10)	P1—N2—C8—C13	143.89 (9)
N3—P1—N2—C8	−164.72 (9)	C14—N2—C8—C9	74.73 (13)
N1—P1—N2—C8	80.35 (9)	P1—N2—C8—C9	−91.36 (11)
O2—P1—N3—C21	−60.31 (12)	N2—C8—C9—C10	178.90 (11)
N2—P1—N3—C21	62.93 (11)	C13—C8—C9—C10	−56.04 (15)
N1—P1—N3—C21	−177.45 (10)	C8—C9—C10—C11	55.54 (17)
O2—P1—N3—C15	99.32 (12)	C9—C10—C11—C12	−55.57 (19)
N2—P1—N3—C15	−137.44 (11)	C10—C11—C12—C13	56.09 (18)
N1—P1—N3—C15	−17.82 (13)	N2—C8—C13—C12	−177.37 (10)
F1—C1—C2—C3	177.59 (14)	C9—C8—C13—C12	57.05 (14)
C6—C1—C2—C3	0.3 (2)	C11—C12—C13—C8	−57.15 (16)
C1—C2—C3—C4	−0.3 (2)	C21—N3—C15—C16	54.69 (16)
C2—C3—C4—C5	0.0 (2)	P1—N3—C15—C16	−104.68 (13)
C3—C4—C5—F2	179.09 (13)	C21—N3—C15—C20	−71.27 (17)
C3—C4—C5—C6	0.2 (2)	P1—N3—C15—C20	129.36 (12)
F2—C5—C6—C1	−179.04 (12)	N3—C15—C16—C17	178.75 (11)
C4—C5—C6—C1	−0.2 (2)	C20—C15—C16—C17	−55.36 (16)
F2—C5—C6—C7	−0.8 (2)	C15—C16—C17—C18	54.61 (19)
C4—C5—C6—C7	178.10 (13)	C16—C17—C18—C19	−55.4 (2)
F1—C1—C6—C5	−177.37 (12)	C17—C18—C19—C20	56.9 (2)
C2—C1—C6—C5	−0.1 (2)	C18—C19—C20—C15	−57.2 (2)
F1—C1—C6—C7	4.3 (2)	N3—C15—C20—C19	−176.48 (14)
C2—C1—C6—C7	−178.47 (13)	C16—C15—C20—C19	56.45 (18)
P1—N1—C7—O1	2.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86 (1)	1.90 (1)	2.7330 (13)	165.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86 (1)	1.90 (1)	2.7330 (13)	165 (1)

Symmetry code: (i) .