N-(2,6-Difluoro­benzo­yl)-P,P-bis­(pyrrolidin-1-yl)phosphinic amide

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

doi:10.1107/S1600536811033216

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2444

doi:10.1107/S1600536811033216

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N-(2,6-Difluorobenzoyl)-P,P-bis(pyrrolidin-1-yl)phosphinic amide

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 3 August 2011; accepted 16 August 2011; online 27 August 2011)

The phosphoryl and carbonyl groups in the title compound, C₁₅H₂₀F₂N₃O₂P, are anti with respect to each other (but the P- and C-groups are separated by another atom) and the P atom is in a tetrahedral coordination environment. Two C atoms in one of the pyrrolidinyl fragments are disordered over two sets of sites with occupancies of 0.746 (8) and 0.254 (8). The environments of the pyrrolidinyl N atoms show a slight deviation from planarity and none of the three N atoms is involved in any hydrogen bond as an acceptor. In the crystal, pairs of intermolecular N—H⋯O hydrogen bonds form inversion dimers.

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 hydrogen-bond strength, see: Pourayoubi et al. (2011). For a related structure, see: Pourayoubi et al. (2010 ). For bond lengths, angles and torsion angles, see: Tarahhomi et al. (2011 ). For graph-set motifs, see Bernstein et al. (1995 ). For a related phosphoric triamide, see: Sabbaghi et al. (2010 ).

Experimental

Crystal data

C₁₅H₂₀F₂N₃O₂P
M_r = 343.31
Monoclinic, P 2₁ /n
a = 10.286 (3) Å
b = 14.873 (4) Å
c = 10.917 (3) Å
β = 99.296 (3)°
V = 1648.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.40 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.925, T_max = 0.952
13279 measured reflections
3776 independent reflections
2953 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.119
S = 1.05
3776 reflections
230 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86 (1)	1.90 (1)	2.757 (2)	175 (2)
Symmetry code: (i) -x+1, -y+1, -z.

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: 10.1107/S1600536811033216/jj2098sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033216/jj2098Isup2.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, C₁₅H₂₀F₂N₃O₂P (Fig. 1), was performed as a continuation of work on this family of compounds in our laboratory.

The carbon atoms C13 and C14 in one of the pyrrolidinyl fragments are disordered over two sets of sites with occupancies of 0.746 (8) and 0.254 (8). The P═O and C═O groups are in anti positions with respect to each other. The P atom is in a distorted tetrahedral environment as has been noted for other phosphoric triamides (Sabbaghi et al., 2010). The nitrogen atoms show sp² character, the average bond angles at the two tertiary N atoms being 117.8 and 118.7°, respectively. The P═O, C═O and P—N bond lengths, P—N—C bond angles and O—P—N—C torsion angles are within the expected values (Tarahhomi et al., 2011).

The P═O group and the N—H unit are syn with respect to one another. In the crystal, pairs of intermolecular N—H···O(P) hydrogen bonds (Table 1) form hydrogen-bonded dimers as R₂²(8) graph-set rings (Bernstein et al., 1995).

Related literature top

For patterns of hydrogen bonds in compounds containing a C(O)NHP(O) skeleton, see: Toghraee et al. (2011); Pourayoubi et al. (2011) and in compounds containing a C(O)NHP(O) skeleton, see: Toghraee et al. (2011). For hydrogen-bond strength, see: Pourayoubi et al. (2011). For a related structure, see: Pourayoubi et al. (2010). For bond lengths, angles and torsion angles, see: Tarahhomi et al. (2011). For graph-set motifs, see Bernstein et al. (1995). For related phosphoric triamides, see: Sabbaghi et al. (2010).

Experimental top

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

To a solution of 2,6—F₂C₆H₃C(O)NHP(O)Cl₂ (0.4 g, 1.46 mmol) in dry chloroform (30 ml), a solution of pyrrolidine (0.415 g, 5.84 mmol) in dry chloroform (10 ml) was added at 0 °C. After 4 h stirring, the solvent was removed and the product was washed with distilled water and recrystallized from a mixture of CH₃OH/DMF (4:1) at room temperature. Single crystals of the title compound were obtained from this solution at room temperature.

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) and Mercury (Macrae et al., 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 of title compound with labeling. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii.

N-(2,6-Difluorobenzoyl)-P,P-bis(pyrrolidin-1-yl)phosphinic amide top

Crystal data top

C₁₅H₂₀F₂N₃O₂P	F(000) = 720
M_r = 343.31	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7152 reflections
a = 10.286 (3) Å	θ = 2.5–27.9°
b = 14.873 (4) Å	µ = 0.20 mm⁻¹
c = 10.917 (3) Å	T = 100 K
β = 99.296 (3)°	Block, colourless
V = 1648.3 (7) Å³	0.40 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3776 independent reflections
Radiation source: fine-focus sealed tube	2953 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→13
T_min = 0.925, T_max = 0.952	k = −19→14
13279 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0419P)² + 1.0825P] where P = (F_o² + 2F_c²)/3
3776 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.39 e Å⁻³
7 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₅H₂₀F₂N₃O₂P	V = 1648.3 (7) Å³
M_r = 343.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.286 (3) Å	µ = 0.20 mm⁻¹
b = 14.873 (4) Å	T = 100 K
c = 10.917 (3) Å	0.40 × 0.30 × 0.25 mm
β = 99.296 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3776 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2953 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.952	R_int = 0.043
13279 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	7 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.39 e Å⁻³
3776 reflections	Δρ_min = −0.41 e Å⁻³
230 parameters

Special details top

Experimental. IR (KBr, ν, cm^-1): 3062 (NH), 2846, 1684, 1622, 1465, 1442, 1284, 1218, 1181, 1092, 1008, 876, 800, 768, 708, 586.

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	0.58132 (4)	0.60634 (4)	0.14444 (5)	0.02623 (15)
F1	0.06841 (11)	0.66217 (8)	0.14052 (12)	0.0357 (3)
F2	0.33806 (10)	0.40553 (8)	0.20332 (11)	0.0333 (3)
O1	0.34013 (13)	0.65942 (10)	0.26101 (14)	0.0340 (4)
O2	0.65277 (12)	0.54022 (11)	0.07877 (12)	0.0322 (4)
N1	0.42250 (14)	0.57290 (13)	0.12010 (15)	0.0283 (4)
H1A	0.402 (2)	0.5349 (12)	0.0604 (16)	0.034*
N2	0.64224 (15)	0.60885 (11)	0.29142 (15)	0.0260 (4)
N3	0.57871 (16)	0.71092 (14)	0.10109 (18)	0.0396 (5)
C1	0.08224 (17)	0.57212 (14)	0.15613 (17)	0.0249 (4)
C2	−0.02954 (17)	0.52080 (14)	0.15101 (18)	0.0282 (4)
H2A	−0.1144	0.5478	0.1386	0.034*
C3	−0.01492 (18)	0.42859 (15)	0.16440 (19)	0.0304 (5)
H3A	−0.0908	0.3919	0.1621	0.036*
C4	0.10900 (19)	0.38887 (14)	0.18117 (18)	0.0284 (4)
H4A	0.1190	0.3256	0.1904	0.034*
C5	0.21675 (17)	0.44419 (14)	0.18402 (17)	0.0260 (4)
C6	0.20909 (16)	0.53694 (13)	0.17294 (16)	0.0225 (4)
C7	0.32904 (17)	0.59659 (14)	0.18895 (17)	0.0249 (4)
C8	0.6309 (2)	0.68401 (14)	0.3773 (2)	0.0328 (5)
H8A	0.5548	0.7229	0.3452	0.039*
H8B	0.7120	0.7209	0.3900	0.039*
C9	0.6109 (3)	0.63821 (17)	0.4964 (2)	0.0440 (6)
H9A	0.5167	0.6244	0.4962	0.053*
H9B	0.6438	0.6761	0.5695	0.053*
C10	0.6916 (3)	0.55236 (17)	0.4966 (2)	0.0450 (6)
H10A	0.6603	0.5057	0.5497	0.054*
H10B	0.7862	0.5641	0.5265	0.054*
C11	0.6688 (2)	0.52362 (14)	0.36086 (18)	0.0334 (5)
H11A	0.7477	0.4934	0.3391	0.040*
H11B	0.5926	0.4823	0.3431	0.040*
C12	0.7037 (2)	0.75855 (18)	0.0940 (3)	0.0512 (7)
H12A	0.7311	0.7953	0.1693	0.061*	0.746 (8)
H12B	0.7748	0.7152	0.0857	0.061*	0.746 (8)
H12C	0.7680	0.7205	0.0597	0.061*	0.254 (8)
H12D	0.7447	0.7840	0.1748	0.061*	0.254 (8)
C13	0.6757 (6)	0.8164 (5)	−0.0173 (6)	0.0601 (19)	0.746 (8)
H13A	0.6871	0.7829	−0.0933	0.072*	0.746 (8)
H13B	0.7335	0.8700	−0.0094	0.072*	0.746 (8)
C14	0.5338 (4)	0.8424 (3)	−0.0195 (4)	0.0520 (13)	0.746 (8)
H14A	0.4933	0.8646	−0.1024	0.062*	0.746 (8)
H14B	0.5252	0.8890	0.0434	0.062*	0.746 (8)
C13A	0.6387 (15)	0.8325 (12)	0.0017 (13)	0.043 (4)	0.254 (8)
H13C	0.6062	0.8819	0.0495	0.051*	0.254 (8)
H13D	0.7061	0.8577	−0.0438	0.051*	0.254 (8)
C14A	0.5278 (10)	0.7968 (8)	−0.0887 (9)	0.048 (3)	0.254 (8)
H14C	0.5559	0.7543	−0.1492	0.057*	0.254 (8)
H14D	0.4704	0.8443	−0.1318	0.057*	0.254 (8)
C15	0.4701 (2)	0.7512 (2)	0.0127 (3)	0.0557 (8)
H15A	0.3910	0.7613	0.0518	0.067*	0.746 (8)
H15B	0.4462	0.7131	−0.0620	0.067*	0.746 (8)
H15C	0.4195	0.7936	0.0565	0.067*	0.254 (8)
H15D	0.4095	0.7034	−0.0250	0.067*	0.254 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0153 (2)	0.0358 (3)	0.0272 (3)	−0.00273 (19)	0.00216 (18)	0.0048 (2)
F1	0.0267 (6)	0.0268 (7)	0.0548 (8)	0.0024 (5)	0.0109 (5)	−0.0006 (6)
F2	0.0230 (5)	0.0356 (7)	0.0407 (7)	0.0057 (5)	0.0034 (5)	0.0040 (5)
O1	0.0278 (7)	0.0339 (9)	0.0410 (8)	−0.0075 (6)	0.0079 (6)	−0.0103 (7)
O2	0.0182 (6)	0.0502 (10)	0.0279 (7)	−0.0018 (6)	0.0030 (5)	−0.0034 (7)
N1	0.0187 (7)	0.0436 (11)	0.0230 (8)	−0.0054 (7)	0.0046 (6)	−0.0037 (8)
N2	0.0261 (8)	0.0215 (9)	0.0284 (8)	−0.0003 (6)	−0.0019 (6)	0.0007 (7)
N3	0.0218 (8)	0.0465 (12)	0.0508 (12)	0.0006 (8)	0.0067 (7)	0.0229 (10)
C1	0.0244 (8)	0.0237 (10)	0.0277 (9)	0.0011 (7)	0.0079 (7)	−0.0022 (8)
C2	0.0179 (8)	0.0351 (12)	0.0325 (10)	−0.0003 (8)	0.0067 (7)	−0.0042 (9)
C3	0.0251 (9)	0.0355 (12)	0.0318 (10)	−0.0099 (8)	0.0083 (8)	−0.0042 (9)
C4	0.0305 (9)	0.0264 (11)	0.0291 (10)	−0.0035 (8)	0.0074 (8)	0.0001 (8)
C5	0.0215 (8)	0.0323 (11)	0.0242 (9)	0.0032 (8)	0.0035 (7)	0.0001 (8)
C6	0.0180 (8)	0.0289 (11)	0.0213 (9)	−0.0024 (7)	0.0055 (7)	−0.0018 (8)
C7	0.0189 (8)	0.0306 (11)	0.0250 (9)	−0.0026 (7)	0.0027 (7)	0.0014 (8)
C8	0.0306 (10)	0.0233 (11)	0.0408 (12)	0.0019 (8)	−0.0047 (8)	−0.0049 (9)
C9	0.0621 (15)	0.0340 (13)	0.0371 (12)	0.0038 (11)	0.0115 (11)	−0.0074 (10)
C10	0.0674 (16)	0.0360 (14)	0.0287 (11)	0.0082 (12)	−0.0009 (11)	−0.0024 (10)
C11	0.0458 (12)	0.0254 (11)	0.0272 (10)	0.0066 (9)	0.0004 (9)	−0.0005 (9)
C12	0.0343 (11)	0.0389 (15)	0.085 (2)	−0.0063 (10)	0.0237 (12)	0.0122 (14)
C13	0.091 (4)	0.038 (3)	0.064 (3)	−0.025 (3)	0.052 (3)	−0.008 (2)
C14	0.081 (3)	0.040 (2)	0.036 (2)	−0.0016 (19)	0.0119 (19)	0.0143 (18)
C13A	0.048 (8)	0.046 (9)	0.035 (7)	−0.004 (6)	0.010 (6)	0.013 (6)
C14A	0.072 (7)	0.037 (6)	0.032 (6)	0.001 (5)	0.004 (5)	0.007 (5)
C15	0.0462 (13)	0.068 (2)	0.0523 (16)	0.0092 (13)	0.0052 (12)	0.0353 (14)

Geometric parameters (Å, º) top

P1—O2	1.4803 (16)	C9—H9B	0.9900
P1—N3	1.625 (2)	C10—C11	1.524 (3)
P1—N2	1.6261 (17)	C10—H10A	0.9900
P1—N1	1.6872 (16)	C10—H10B	0.9900
F1—C1	1.355 (2)	C11—H11A	0.9900
F2—C5	1.359 (2)	C11—H11B	0.9900
O1—C7	1.215 (2)	C12—C13	1.479 (7)
N1—C7	1.359 (2)	C12—C13A	1.566 (14)
N1—H1A	0.863 (9)	C12—H12A	0.9900
N2—C8	1.476 (3)	C12—H12B	0.9900
N2—C11	1.480 (3)	C12—H12C	0.9891
N3—C15	1.480 (3)	C12—H12D	0.9903
N3—C12	1.481 (3)	C13—C14	1.507 (7)
C1—C2	1.374 (3)	C13—H13A	0.9900
C1—C6	1.390 (2)	C13—H13B	0.9900
C2—C3	1.385 (3)	C14—C15	1.571 (4)
C2—H2A	0.9500	C14—H14A	0.9900
C3—C4	1.390 (3)	C14—H14B	0.9900
C3—H3A	0.9500	C13A—C14A	1.481 (15)
C4—C5	1.377 (3)	C13A—H13C	0.9900
C4—H4A	0.9500	C13A—H13D	0.9900
C5—C6	1.386 (3)	C14A—C15	1.500 (9)
C6—C7	1.507 (2)	C14A—H14C	0.9900
C8—C9	1.512 (3)	C14A—H14D	0.9900
C8—H8A	0.9900	C15—H15A	0.9900
C8—H8B	0.9900	C15—H15B	0.9900
C9—C10	1.523 (3)	C15—H15C	0.9892
C9—H9A	0.9900	C15—H15D	0.9898

O2—P1—N3	118.75 (10)	C13—C12—N3	105.4 (3)
O2—P1—N2	110.54 (8)	N3—C12—C13A	94.9 (6)
N3—P1—N2	104.53 (10)	C13—C12—H12A	110.7
O2—P1—N1	105.77 (9)	N3—C12—H12A	110.7
N3—P1—N1	105.44 (9)	C13A—C12—H12A	100.4
N2—P1—N1	111.79 (8)	C13—C12—H12B	110.7
C7—N1—P1	126.16 (14)	N3—C12—H12B	110.7
C7—N1—H1A	118.4 (15)	C13A—C12—H12B	130.1
P1—N1—H1A	115.3 (15)	H12A—C12—H12B	108.8
C8—N2—C11	110.53 (16)	C13—C12—H12C	94.3
C8—N2—P1	125.92 (13)	N3—C12—H12C	112.7
C11—N2—P1	119.72 (13)	C13A—C12—H12C	113.6
C15—N3—C12	110.05 (19)	H12A—C12—H12C	120.9
C15—N3—P1	123.53 (17)	C13—C12—H12D	120.5
C12—N3—P1	119.96 (15)	N3—C12—H12D	112.6
F1—C1—C2	118.29 (16)	C13A—C12—H12D	112.4
F1—C1—C6	117.78 (16)	H12B—C12—H12D	96.8
C2—C1—C6	123.90 (19)	H12C—C12—H12D	110.0
C1—C2—C3	118.04 (17)	C12—C13—C14	102.8 (4)
C1—C2—H2A	121.0	C12—C13—H13A	111.2
C3—C2—H2A	121.0	C14—C13—H13A	111.2
C2—C3—C4	121.09 (18)	C12—C13—H13B	111.2
C2—C3—H3A	119.5	C14—C13—H13B	111.2
C4—C3—H3A	119.5	H13A—C13—H13B	109.1
C5—C4—C3	117.83 (19)	C13—C14—C15	102.3 (4)
C5—C4—H4A	121.1	C13—C14—H14A	111.3
C3—C4—H4A	121.1	C15—C14—H14A	111.3
F2—C5—C4	117.79 (18)	C13—C14—H14B	111.3
F2—C5—C6	118.20 (16)	C15—C14—H14B	111.3
C4—C5—C6	123.97 (17)	H14A—C14—H14B	109.2
C5—C6—C1	115.16 (16)	C14A—C13A—C12	112.3 (12)
C5—C6—C7	122.82 (16)	C14A—C13A—H13C	109.1
C1—C6—C7	121.82 (18)	C12—C13A—H13C	109.1
O1—C7—N1	123.83 (17)	C14A—C13A—H13D	109.1
O1—C7—C6	121.16 (17)	C12—C13A—H13D	109.1
N1—C7—C6	114.99 (17)	H13C—C13A—H13D	107.9
N2—C8—C9	103.94 (17)	C13A—C14A—C15	91.4 (9)
N2—C8—H8A	111.0	C13A—C14A—H14C	113.4
C9—C8—H8A	111.0	C15—C14A—H14C	113.4
N2—C8—H8B	111.0	C13A—C14A—H14D	113.4
C9—C8—H8B	111.0	C15—C14A—H14D	113.4
H8A—C8—H8B	109.0	H14C—C14A—H14D	110.7
C8—C9—C10	103.24 (19)	N3—C15—C14A	108.5 (4)
C8—C9—H9A	111.1	N3—C15—C14	101.4 (2)
C10—C9—H9A	111.1	N3—C15—H15A	111.5
C8—C9—H9B	111.1	C14A—C15—H15A	134.5
C10—C9—H9B	111.1	C14—C15—H15A	111.5
H9A—C9—H9B	109.1	N3—C15—H15B	111.5
C9—C10—C11	103.61 (18)	C14A—C15—H15B	74.1
C9—C10—H10A	111.0	C14—C15—H15B	111.5
C11—C10—H10A	111.0	H15A—C15—H15B	109.3
C9—C10—H10B	111.0	N3—C15—H15C	110.1
C11—C10—H10B	111.0	C14A—C15—H15C	111.7
H10A—C10—H10B	109.0	C14—C15—H15C	80.1
N2—C11—C10	104.16 (17)	H15B—C15—H15C	133.1
N2—C11—H11A	110.9	N3—C15—H15D	109.8
C10—C11—H11A	110.9	C14A—C15—H15D	108.4
N2—C11—H11B	110.9	C14—C15—H15D	141.7
C10—C11—H11B	110.9	H15A—C15—H15D	77.4
H11A—C11—H11B	108.9	H15C—C15—H15D	108.3

O2—P1—N1—C7	160.11 (17)	P1—N1—C7—C6	−162.13 (14)
N3—P1—N1—C7	−73.26 (19)	C5—C6—C7—O1	−126.8 (2)
N2—P1—N1—C7	39.7 (2)	C1—C6—C7—O1	47.8 (3)
O2—P1—N2—C8	157.70 (16)	C5—C6—C7—N1	51.5 (2)
N3—P1—N2—C8	28.81 (18)	C1—C6—C7—N1	−133.96 (19)
N1—P1—N2—C8	−84.76 (18)	C11—N2—C8—C9	−16.4 (2)
O2—P1—N2—C11	−46.49 (17)	P1—N2—C8—C9	141.28 (16)
N3—P1—N2—C11	−175.38 (15)	N2—C8—C9—C10	33.4 (2)
N1—P1—N2—C11	71.05 (17)	C8—C9—C10—C11	−38.2 (2)
O2—P1—N3—C15	95.4 (2)	C8—N2—C11—C10	−7.4 (2)
N2—P1—N3—C15	−140.9 (2)	P1—N2—C11—C10	−166.62 (15)
N1—P1—N3—C15	−22.9 (2)	C9—C10—C11—N2	28.0 (2)
O2—P1—N3—C12	−53.6 (2)	C15—N3—C12—C13	−11.0 (4)
N2—P1—N3—C12	70.2 (2)	P1—N3—C12—C13	141.7 (3)
N1—P1—N3—C12	−171.80 (19)	C15—N3—C12—C13A	5.5 (7)
F1—C1—C2—C3	178.66 (18)	P1—N3—C12—C13A	158.3 (6)
C6—C1—C2—C3	0.5 (3)	N3—C12—C13—C14	33.6 (5)
C1—C2—C3—C4	−0.7 (3)	C13A—C12—C13—C14	−25 (2)
C2—C3—C4—C5	0.0 (3)	C12—C13—C14—C15	−42.7 (5)
C3—C4—C5—F2	178.50 (17)	C13—C12—C13A—C14A	89 (3)
C3—C4—C5—C6	0.9 (3)	N3—C12—C13A—C14A	−35.5 (12)
F2—C5—C6—C1	−178.62 (16)	C12—C13A—C14A—C15	47.7 (13)
C4—C5—C6—C1	−1.1 (3)	C12—N3—C15—C14A	23.9 (6)
F2—C5—C6—C7	−3.8 (3)	P1—N3—C15—C14A	−127.7 (5)
C4—C5—C6—C7	173.80 (18)	C12—N3—C15—C14	−15.1 (3)
F1—C1—C6—C5	−177.82 (17)	P1—N3—C15—C14	−166.7 (2)
C2—C1—C6—C5	0.3 (3)	C13A—C14A—C15—N3	−40.9 (10)
F1—C1—C6—C7	7.3 (3)	C13A—C14A—C15—C14	44.1 (8)
C2—C1—C6—C7	−174.62 (18)	C13—C14—C15—N3	35.1 (4)
P1—N1—C7—O1	16.1 (3)	C13—C14—C15—C14A	−70.4 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86 (1)	1.90 (1)	2.757 (2)	175 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₀F₂N₃O₂P
M_r	343.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.286 (3), 14.873 (4), 10.917 (3)
β (°)	99.296 (3)
V (Å³)	1648.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.40 × 0.30 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.925, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	13279, 3776, 2953
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.119, 1.05
No. of reflections	3776
No. of parameters	230
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.41

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 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—H1A···O2ⁱ	0.863 (9)	1.896 (10)	2.757 (2)	175 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

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

References

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