N,N,N′,N′-Tetra­ethyl-N′′-(2-fluoro­benzo­yl)phospho­ric triamide

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

doi:10.1107/S1600536811036944

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2643

https://doi.org/10.1107/S1600536811036944

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N,N,N′,N′-Tetraethyl-N′′-(2-fluorobenzoyl)phosphoric triamide

Atekeh Tarahhomi,^a Mehrdad Pourayoubi,^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 6 August 2011; accepted 12 September 2011; online 14 September 2011)

In the title compound, C₁₅H₂₅FN₃O₂P, the phosphoryl group is in an anti and syn orientation to the C=O and N—H groups, respectively. The P atom is in a distorted tetrahedral environment. One of the ethyl groups is disordered over two sets of sites with refined occupancies of 0.755 (6) and 0.245 (6). In addition, the F atom was refined as disordered with occupancies fixed at 0.9 and 0.1. This disorder corresponds to a rotation of approximately 180° of the fluorobenzene ring about its connecting C—C bond. In the crystal, pairs of intermolecular N—H⋯O(=P) hydrogen bonds form centrosymmetric dimers.

Related literature

For background to phosphoric triamide compounds containing a C(=O)NHP(=O) skeleton, see: Pourayoubi et al. (2011a ,b ); Tarahhomi et al. (2011 ). For the synthesis of the starting material 2-F—C₆H₄C(=O)NHP(=O)Cl₂, see: Pourayoubi et al. (2011a). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₂₅FN₃O₂P
M_r = 329.35
Monoclinic, P 2₁ /c
a = 10.9296 (9) Å
b = 12.2221 (10) Å
c = 12.3423 (10) Å
β = 91.443 (1)°
V = 1648.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.45 × 0.40 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.920, T_max = 0.937
11336 measured reflections
3741 independent reflections
3056 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.122
S = 1.08
3741 reflections
236 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.42 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 (2)	1.93 (2)	2.7714 (19)	167 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

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: 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: https://doi.org/10.1107/S1600536811036944/lh5308sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811036944/lh5308Isup2.hkl

checkCIF report

Comment top

Following our previous work on phosphoric triamides containing an XC(O)NHP(O) moiety, X = 2-F—C₆H₄ (Pourayoubi et al., 2011a), 4-F—C₆H₄ (Tarahhomi et al., 2011) and 2,6-F₂—C₆H₃ (Pourayoubi et al., 2011b), herein, we report the synthesis and crystal structure of the title compound, P(O)[2-F—C₆H₄C(O)NH][N(C₂H₅)₂]₂ (Fig. 1).

One of the —CH₂CH₃ groups in the diethylamido substituent N2 is disordered over two sets of sites with refined occupancies of 0.755 (6) and 0.245 (6). The fluorine atom of the aromatic ring is disordered over two sets of sites with occupancies of 0.9 and 0.1.

In the C(═O)NHP(═O) skeleton of 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 has been noted for the other phosphoric triamides. The P═O, C═O and P—N bond lengths are within the expected values (Pourayoubi et al. (2011b) and Tarahhomi et al. (2011)).

In the crystal, pairs of intermolecular N—H···O(P) hydrogen bonds form a hydrogen-bonded dimer with R₂²(8) graph-set notation (Bernstein et al., 1995).

Related literature top

For background to phosphoric triamide compounds containing a C(═O)NHP(═ O) skeleton, see: Pourayoubi et al. (2011a,b); Tarahhomi et al. (2011). For the synthesis of the starting material 2-F—C₆H₄C(═O)NHP(═O)Cl₂, see: Pourayoubi et al. (2011a). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

2-F—C₆H₄C(O)NHP(O)Cl₂ was prepared according to the literature method reported by Pourayoubi et al. (2011a).

The title compound was synthesized from the reaction of 0.40 g (1.56 mmol) 2-F—C₆H₄C(O)NHP(O)Cl₂ with 0.456 g (6.24 mmol) of diethyl amine in dry chloroform (30 ml). The amine was added dropwise to a solution of 2-F—C₆H₄C(O)NHP(O)Cl₂ at 273 K, with continuous stirring. After 17 h, the solvent was evaporated; the obtained solid was washed with distilled water and dissolved in a mixture of CH₃OH/DMF [4:1 (v/v)]. Single crystals were obtained from this solution after a few days at room temperature. IR (KBr, ν, cm^-1): 3061 (NH), 2970, 2886, 1675 (C═O), 1457, 1196, 1048, 946, 766.

Structure description top

In the crystal, pairs of intermolecular N—H···O(P) hydrogen bonds form a hydrogen-bonded dimer with R₂²(8) graph-set notation (Bernstein et al., 1995).

Computing details top

Data collection: APEX2 (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. The molecular structure of the title compound. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii. Disordered atoms are labeled with the suffix 'A'.

N,N,N',N'-Tetraethyl-N''-(2- fluorobenzoyl)phosphoric triamide top

Crystal data top

C₁₅H₂₅FN₃O₂P	F(000) = 704
M_r = 329.35	D_x = 1.327 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6938 reflections
a = 10.9296 (9) Å	θ = 2.5–27.9°
b = 12.2221 (10) Å	µ = 0.19 mm⁻¹
c = 12.3423 (10) Å	T = 100 K
β = 91.443 (1)°	Block, colourless
V = 1648.2 (2) Å³	0.45 × 0.40 × 0.35 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3741 independent reflections
Radiation source: fine-focus sealed tube	3056 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
φ and ω scans	θ_max = 28.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→7
T_min = 0.920, T_max = 0.937	k = −16→14
11336 measured reflections	l = −15→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0487P)² + 0.7763P] where P = (F_o² + 2F_c²)/3
3741 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.55 e Å⁻³
6 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₅H₂₅FN₃O₂P	V = 1648.2 (2) Å³
M_r = 329.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9296 (9) Å	µ = 0.19 mm⁻¹
b = 12.2221 (10) Å	T = 100 K
c = 12.3423 (10) Å	0.45 × 0.40 × 0.35 mm
β = 91.443 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3741 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3056 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.937	R_int = 0.051
11336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	6 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.55 e Å⁻³
3741 reflections	Δρ_min = −0.42 e Å⁻³
236 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
P1	0.62104 (4)	0.64819 (4)	0.52994 (4)	0.01901 (14)
F1	0.88953 (13)	0.41423 (11)	0.83105 (10)	0.0338 (3)	0.90
F1A	0.7449 (9)	0.3460 (7)	0.4748 (4)	0.019 (2)	0.10
O1	0.83305 (12)	0.57884 (11)	0.68306 (10)	0.0259 (3)
O2	0.52742 (11)	0.62160 (11)	0.44464 (10)	0.0230 (3)
N1	0.66071 (13)	0.52777 (13)	0.58794 (12)	0.0199 (3)
H1N	0.6116 (17)	0.4741 (15)	0.5750 (16)	0.024*
N2	0.57927 (14)	0.72748 (13)	0.62914 (12)	0.0260 (4)
N3	0.73894 (13)	0.70810 (12)	0.47587 (11)	0.0201 (3)
C1	0.86735 (17)	0.34892 (16)	0.74688 (15)	0.0254 (4)
H1A	0.8811	0.3968	0.8066	0.030*	0.10
C2	0.91255 (17)	0.24343 (17)	0.75327 (17)	0.0303 (5)
H2	0.9557	0.2194	0.8167	0.036*
C3	0.89453 (18)	0.17367 (17)	0.66716 (17)	0.0300 (4)
H3	0.9265	0.1014	0.6704	0.036*
C4	0.82999 (18)	0.20843 (16)	0.57575 (16)	0.0289 (4)
H4	0.8176	0.1603	0.5161	0.035*
C5	0.78342 (17)	0.31405 (16)	0.57156 (15)	0.0243 (4)
H5A	0.7374	0.3366	0.5092	0.029*	0.90
C6	0.80224 (15)	0.38782 (15)	0.65610 (14)	0.0200 (4)
C7	0.76718 (16)	0.50656 (15)	0.64574 (13)	0.0203 (4)
C8	0.5579 (3)	0.8451 (2)	0.6092 (2)	0.0279 (7)	0.755 (6)
H8A	0.5829	0.8629	0.5347	0.034*	0.755 (6)
H8B	0.6103	0.8880	0.6601	0.034*	0.755 (6)
C9	0.4260 (3)	0.8792 (3)	0.6222 (3)	0.0463 (10)	0.755 (6)
H9A	0.4164	0.9562	0.6016	0.069*	0.755 (6)
H9B	0.4033	0.8698	0.6980	0.069*	0.755 (6)
H9C	0.3728	0.8338	0.5756	0.069*	0.755 (6)
C8A	0.4916 (9)	0.8158 (7)	0.5807 (7)	0.032 (2)	0.245 (6)
H8AA	0.5086	0.8280	0.5032	0.038*	0.245 (6)
H8AB	0.4054	0.7922	0.5867	0.038*	0.245 (6)
C9A	0.5141 (8)	0.9196 (7)	0.6449 (7)	0.033 (3)	0.245 (6)
H9AA	0.4629	0.9785	0.6147	0.049*	0.245 (6)
H9AB	0.6005	0.9403	0.6409	0.049*	0.245 (6)
H9AC	0.4935	0.9073	0.7208	0.049*	0.245 (6)
C10	0.54246 (19)	0.68425 (18)	0.73515 (15)	0.0297 (4)
H10A	0.5370	0.7459	0.7868	0.036*
H10B	0.6071	0.6341	0.7629	0.036*
C11	0.4206 (2)	0.6232 (2)	0.7324 (2)	0.0485 (6)
H11A	0.3562	0.6713	0.7029	0.073*
H11B	0.4002	0.6010	0.8061	0.073*
H11C	0.4271	0.5582	0.6865	0.073*
C12	0.78030 (17)	0.66718 (17)	0.37025 (15)	0.0260 (4)
H12A	0.8211	0.7276	0.3318	0.031*
H12B	0.7077	0.6450	0.3259	0.031*
C13	0.86787 (19)	0.57083 (18)	0.37903 (18)	0.0358 (5)
H13A	0.9365	0.5897	0.4281	0.054*
H13B	0.8989	0.5536	0.3072	0.054*
H13C	0.8247	0.5071	0.4074	0.054*
C14	0.82939 (17)	0.77616 (15)	0.53521 (15)	0.0241 (4)
H14A	0.9105	0.7403	0.5329	0.029*
H14B	0.8062	0.7812	0.6121	0.029*
C15	0.8391 (2)	0.89111 (17)	0.48869 (18)	0.0343 (5)
H15A	0.8554	0.8867	0.4111	0.051*
H15B	0.9060	0.9304	0.5259	0.051*
H15C	0.7620	0.9303	0.4991	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0162 (2)	0.0221 (3)	0.0187 (2)	0.00183 (17)	0.00024 (16)	0.00116 (17)
F1	0.0485 (8)	0.0294 (7)	0.0229 (6)	0.0034 (6)	−0.0118 (6)	−0.0017 (5)
F1A	0.025 (5)	0.014 (5)	0.018 (5)	0.003 (4)	−0.003 (4)	0.003 (4)
O1	0.0268 (7)	0.0235 (7)	0.0271 (7)	−0.0039 (6)	−0.0082 (5)	0.0007 (5)
O2	0.0172 (6)	0.0280 (7)	0.0236 (6)	−0.0007 (5)	−0.0028 (5)	0.0052 (5)
N1	0.0158 (7)	0.0218 (8)	0.0220 (7)	−0.0009 (6)	−0.0011 (5)	0.0005 (6)
N2	0.0284 (8)	0.0253 (8)	0.0245 (8)	0.0068 (7)	0.0064 (6)	0.0005 (6)
N3	0.0192 (7)	0.0224 (8)	0.0186 (7)	−0.0011 (6)	−0.0006 (5)	−0.0006 (6)
C1	0.0255 (9)	0.0283 (10)	0.0221 (9)	−0.0044 (8)	−0.0043 (7)	0.0018 (7)
C2	0.0247 (9)	0.0319 (11)	0.0338 (11)	0.0001 (8)	−0.0069 (8)	0.0140 (9)
C3	0.0236 (10)	0.0250 (10)	0.0414 (12)	0.0022 (8)	0.0037 (8)	0.0071 (9)
C4	0.0309 (10)	0.0237 (10)	0.0323 (10)	−0.0007 (8)	0.0043 (8)	−0.0004 (8)
C5	0.0254 (9)	0.0253 (10)	0.0222 (9)	0.0001 (8)	−0.0007 (7)	0.0025 (7)
C6	0.0152 (8)	0.0223 (9)	0.0223 (9)	−0.0007 (7)	0.0006 (6)	0.0043 (7)
C7	0.0198 (8)	0.0241 (9)	0.0170 (8)	−0.0002 (7)	0.0011 (6)	0.0021 (7)
C8	0.0256 (16)	0.0286 (15)	0.0294 (15)	0.0069 (12)	−0.0018 (12)	−0.0034 (11)
C9	0.0295 (17)	0.0396 (19)	0.069 (2)	0.0107 (14)	−0.0061 (14)	−0.0157 (16)
C8A	0.036 (5)	0.033 (5)	0.026 (4)	0.020 (4)	−0.017 (4)	−0.011 (4)
C9A	0.038 (5)	0.029 (5)	0.031 (4)	0.013 (4)	−0.003 (4)	−0.007 (4)
C10	0.0339 (11)	0.0328 (11)	0.0229 (10)	−0.0025 (9)	0.0099 (8)	−0.0048 (8)
C11	0.0439 (14)	0.0531 (16)	0.0498 (14)	−0.0144 (12)	0.0241 (11)	−0.0154 (12)
C12	0.0223 (9)	0.0356 (11)	0.0203 (9)	−0.0060 (8)	0.0034 (7)	−0.0037 (8)
C13	0.0316 (11)	0.0344 (12)	0.0420 (12)	−0.0005 (9)	0.0155 (9)	−0.0062 (9)
C14	0.0246 (9)	0.0221 (9)	0.0255 (9)	−0.0045 (8)	−0.0025 (7)	−0.0002 (7)
C15	0.0424 (12)	0.0231 (10)	0.0375 (11)	−0.0042 (9)	0.0012 (9)	0.0017 (9)

Geometric parameters (Å, º) top

P1—O2	1.4855 (13)	C9—H9A	0.9800
P1—N2	1.6354 (16)	C9—H9B	0.9800
P1—N3	1.6387 (15)	C9—H9C	0.9800
P1—N1	1.6885 (16)	C8A—C9A	1.513 (11)
O1—C7	1.222 (2)	C8A—H8AA	0.9900
N1—C7	1.374 (2)	C8A—H8AB	0.9900
N1—H1N	0.860 (15)	C9A—H9AA	0.9800
N2—C8	1.476 (3)	C9A—H9AB	0.9800
N2—C10	1.476 (2)	C9A—H9AC	0.9800
N2—C8A	1.553 (7)	C10—C11	1.526 (3)
N3—C14	1.473 (2)	C10—H10A	0.9900
N3—C12	1.478 (2)	C10—H10B	0.9900
C1—C2	1.382 (3)	C11—H11A	0.9800
C1—C6	1.396 (2)	C11—H11B	0.9800
C1—H1A	0.9500	C11—H11C	0.9800
C2—C3	1.373 (3)	C12—C13	1.520 (3)
C2—H2	0.9500	C12—H12A	0.9900
C3—C4	1.382 (3)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9800
C4—C5	1.388 (3)	C13—H13B	0.9800
C4—H4	0.9500	C13—H13C	0.9800
C5—C6	1.390 (3)	C14—C15	1.522 (3)
C5—H5A	0.9500	C14—H14A	0.9900
C6—C7	1.506 (3)	C14—H14B	0.9900
C8—C9	1.514 (4)	C15—H15A	0.9800
C8—H8A	0.9900	C15—H15B	0.9800
C8—H8B	0.9900	C15—H15C	0.9800

O2—P1—N2	117.38 (8)	N2—C8A—H8AA	110.3
O2—P1—N3	110.11 (7)	C9A—C8A—H8AB	110.3
N2—P1—N3	106.10 (8)	N2—C8A—H8AB	110.3
O2—P1—N1	105.95 (8)	H8AA—C8A—H8AB	108.6
N2—P1—N1	105.82 (8)	C8A—C9A—H9AA	109.5
N3—P1—N1	111.47 (8)	C8A—C9A—H9AB	109.5
C7—N1—P1	126.13 (13)	H9AA—C9A—H9AB	109.5
C7—N1—H1N	118.0 (14)	C8A—C9A—H9AC	109.5
P1—N1—H1N	115.7 (14)	H9AA—C9A—H9AC	109.5
C8—N2—C10	116.79 (17)	H9AB—C9A—H9AC	109.5
C8—N2—C8A	33.4 (4)	N2—C10—C11	114.35 (18)
C10—N2—C8A	114.2 (4)	N2—C10—H10A	108.7
C8—N2—P1	119.88 (15)	C11—C10—H10A	108.7
C10—N2—P1	122.61 (14)	N2—C10—H10B	108.7
C8A—N2—P1	107.7 (3)	C11—C10—H10B	108.7
C14—N3—C12	114.42 (14)	H10A—C10—H10B	107.6
C14—N3—P1	125.08 (12)	C10—C11—H11A	109.5
C12—N3—P1	117.98 (12)	C10—C11—H11B	109.5
C2—C1—C6	122.54 (18)	H11A—C11—H11B	109.5
C2—C1—H1A	118.7	C10—C11—H11C	109.5
C6—C1—H1A	118.7	H11A—C11—H11C	109.5
C3—C2—C1	119.41 (18)	H11B—C11—H11C	109.5
C3—C2—H2	120.3	N3—C12—C13	113.92 (16)
C1—C2—H2	120.3	N3—C12—H12A	108.8
C2—C3—C4	120.08 (19)	C13—C12—H12A	108.8
C2—C3—H3	120.0	N3—C12—H12B	108.8
C4—C3—H3	120.0	C13—C12—H12B	108.8
C3—C4—C5	119.69 (19)	H12A—C12—H12B	107.7
C3—C4—H4	120.2	C12—C13—H13A	109.5
C5—C4—H4	120.2	C12—C13—H13B	109.5
C4—C5—C6	121.87 (17)	H13A—C13—H13B	109.5
C4—C5—H5A	119.1	C12—C13—H13C	109.5
C6—C5—H5A	119.1	H13A—C13—H13C	109.5
C5—C6—C1	116.39 (17)	H13B—C13—H13C	109.5
C5—C6—C7	121.92 (15)	N3—C14—C15	112.69 (16)
C1—C6—C7	121.34 (16)	N3—C14—H14A	109.1
O1—C7—N1	122.84 (17)	C15—C14—H14A	109.1
O1—C7—C6	121.22 (15)	N3—C14—H14B	109.1
N1—C7—C6	115.87 (15)	C15—C14—H14B	109.1
N2—C8—C9	113.5 (2)	H14A—C14—H14B	107.8
N2—C8—H8A	108.9	C14—C15—H15A	109.5
C9—C8—H8A	108.9	C14—C15—H15B	109.5
N2—C8—H8B	108.9	H15A—C15—H15B	109.5
C9—C8—H8B	108.9	C14—C15—H15C	109.5
H8A—C8—H8B	107.7	H15A—C15—H15C	109.5
C9A—C8A—N2	106.9 (6)	H15B—C15—H15C	109.5
C9A—C8A—H8AA	110.3

O2—P1—N1—C7	158.75 (14)	C4—C5—C6—C7	171.39 (17)
N2—P1—N1—C7	−75.93 (16)	C2—C1—C6—C5	0.7 (3)
N3—P1—N1—C7	38.97 (17)	C2—C1—C6—C7	−172.59 (17)
O2—P1—N2—C8	−72.0 (2)	P1—N1—C7—O1	17.5 (3)
N3—P1—N2—C8	51.5 (2)	P1—N1—C7—C6	−159.56 (12)
N1—P1—N2—C8	170.05 (18)	C5—C6—C7—O1	−139.50 (18)
O2—P1—N2—C10	97.97 (16)	C1—C6—C7—O1	33.4 (3)
N3—P1—N2—C10	−138.49 (15)	C5—C6—C7—N1	37.6 (2)
N1—P1—N2—C10	−19.96 (17)	C1—C6—C7—N1	−149.49 (17)
O2—P1—N2—C8A	−37.8 (5)	C10—N2—C8—C9	−56.1 (3)
N3—P1—N2—C8A	85.7 (5)	C8A—N2—C8—C9	37.9 (6)
N1—P1—N2—C8A	−155.7 (5)	P1—N2—C8—C9	114.5 (2)
O2—P1—N3—C14	159.56 (14)	C8—N2—C8A—C9A	−28.3 (5)
N2—P1—N3—C14	31.58 (16)	C10—N2—C8A—C9A	74.1 (8)
N1—P1—N3—C14	−83.15 (16)	P1—N2—C8A—C9A	−146.0 (6)
O2—P1—N3—C12	−39.48 (15)	C8—N2—C10—C11	100.8 (2)
N2—P1—N3—C12	−167.46 (13)	C8A—N2—C10—C11	63.7 (5)
N1—P1—N3—C12	77.81 (15)	P1—N2—C10—C11	−69.5 (2)
C6—C1—C2—C3	0.7 (3)	C14—N3—C12—C13	77.6 (2)
C1—C2—C3—C4	−1.0 (3)	P1—N3—C12—C13	−85.37 (18)
C2—C3—C4—C5	−0.1 (3)	C12—N3—C14—C15	75.8 (2)
C3—C4—C5—C6	1.6 (3)	P1—N3—C14—C15	−122.62 (16)
C4—C5—C6—C1	−1.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86 (2)	1.93 (2)	2.7714 (19)	167 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₅FN₃O₂P
M_r	329.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.9296 (9), 12.2221 (10), 12.3423 (10)
β (°)	91.443 (1)
V (Å³)	1648.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.45 × 0.40 × 0.35

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.920, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	11336, 3741, 3056
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.122, 1.08
No. of reflections	3741
No. of parameters	236
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.42

Computer programs: APEX2 (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	0.860 (15)	1.928 (16)	2.7714 (19)	167 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

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