N,N′-Dicyclo­hexyl-N′′-(2,6-difluoro­benzo­yl)-N,N′-dimethyl­phospho­ric triamide

Pourayoubi, M.; Tarahhomi, A.; Rheingold, A.L.; Golen, J.A.

doi:10.1107/S1600536811043029

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3027

doi:10.1107/S1600536811043029

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N,N′-Dicyclohexyl-N′′-(2,6-difluorobenzoyl)-N,N′-dimethylphosphoric triamide

Mehrdad Pourayoubi,^a ^* Atekeh Tarahhomi,^a Arnold L. Rheingold ^b and James A. Golen ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 20 September 2011; accepted 17 October 2011; online 22 October 2011)

In the title molecule, C₂₁H₃₂F₂N₃O₂P, the P=O and N—H groups are syn with respect to each other, and the P atom is bonded in a distorted tetrahedral 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 sp² character. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(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_r = 427.47
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.05
5053 reflections
267 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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) -x+1, -y+1, -z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043029/bh2384sup1.cif

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

checkCIF report

Comment top

The patterns of hydrogen bonds and their strengths on phosphoric triamides containing a C(O)NHP(O) skeleton have been discussed (Toghraee et al., 2011; Pourayoubi et al., 2011). The structure determination of the title compound, P(O)[2,6-F₂—C₆H₃C(O)NH][N(CH₃)C₆H₁₁]₂ (Fig. 1), was performed as part of a project in our laboratory on the synthesis of new derivatives of benzoyl phosphoric triamides with formula XC₆H_nC(O)NHP(O)Y₂ (for example, n = 3, X = 2,6-F₂ and Y = NHC(CH₃)₃: Pourayoubi et al., 2010).

In the title phosphoric triamide, the phosphoryl group adopts the anti orientation with respect to the carbonyl group; whereas it is in a syn position relative to the N—H unit. The tetrahedral environment at the P atom is distorted, as previously noted for other phosphoric triamides (Amirkhanov et al., 2010). The P═O, C═O and P—N bond lengths are within the expected ranges (Tarahhomi et al., 2011).

The hydrogen atom of the C(═O)NHP(═O) moiety is involved in an intermolecular –P═O···H—N– hydrogen bond. Pairs of this type of hydrogen bonds form hydrogen-bonded dimers in the crystal (as R₂²(8) rings; see: Bernstein et al., 1995).

Related literature top

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 top

2,6—F₂C₆H₃C(O)NHP(O)Cl₂ was prepared according to the literature method reported by Pourayoubi et al. (2010).

The title compound was synthesized from the reaction of 2,6—F₂C₆H₃C(O)NHP(O)Cl₂ (1.09 mmol) with N-methylcyclohexylamine (4.36 mmol) in dry chloroform (30 ml). The amine was added dropwise to a solution of 2,6—F₂C₆H₃C(O)NHP(O)Cl₂ at 273 K, with continuous stirring. After 4 h, the solvent was evaporated and the obtained solid was washed with distilled water and recrystallized from a mixture of chloroform and DMF (4:1 v/v) at room temperature. IR (KBr, ν, cm^-1): 3063 (NH), 2912, 2752, 1698, 1608, 1470, 1262, 1192, 1155, 997, 864, 815.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures top

Fig. 1. An ORTEP-style plot for the title compound. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii.

N,N'-Dicyclohexyl-N''-(2,6- difluorobenzoyl)-N,N'-dimethylphosphoric triamide top

Crystal data top

C₂₁H₃₂F₂N₃O₂P	Z = 2
M_r = 427.47	F(000) = 456
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0429P)² + 0.4607P] where P = (F_o² + 2F_c²)/3
5053 reflections	(Δ/σ)_max < 0.001
267 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.34 e Å⁻³
0 constraints

Crystal data top

C₂₁H₃₂F₂N₃O₂P	γ = 81.536 (1)°
M_r = 427.47	V = 1121.45 (10) Å³
Triclinic, P1	Z = 2
a = 10.2322 (6) Å	Mo Kα radiation
b = 10.6188 (5) Å	µ = 0.16 mm⁻¹
c = 11.2658 (6) Å	T = 100 K
α = 69.419 (1)°	0.35 × 0.30 × 0.25 mm
β = 79.269 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5053 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4421 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.961	R_int = 0.029
17147 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.32 e Å⁻³
5053 reflections	Δρ_min = −0.34 e Å⁻³
267 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₃₂F₂N₃O₂P
M_r	427.47
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.2322 (6), 10.6188 (5), 11.2658 (6)
α, β, γ (°)	69.419 (1), 79.269 (1), 81.536 (1)
V (Å³)	1121.45 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.946, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	17147, 5053, 4421
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.05
No. of reflections	5053
No. of parameters	267
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.34

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.859 (9)	1.895 (10)	2.7330 (13)	164.5 (14)

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Pourayoubi, M., Tarahhomi, A., Rheingold, A. L. & Golen, J. A. (2010). Acta Cryst. E66, o3159. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265–o272. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tarahhomi, A., Pourayoubi, M., Rheingold, A. L. & Golen, J. A. (2011). Struct. Chem. 22, 201–210. Web of Science CSD CrossRef CAS Google Scholar
Toghraee, M., Pourayoubi, M. & Divjakovic, V. (2011). Polyhedron, 30, 1680–1690. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 11| November 2011| Page o3027

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N,N′-Di­cyclo­hexyl-N′′-(2,6-di­fluoro­benzo­yl)-N,N′-di­methyl­phospho­ric tri­amide

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Acknowledgements

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