N-(4-Fluoro­benzo­yl)-N′,N′′-diisopropyl­phospho­ric triamide

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

doi:10.1107/S1600536812046326

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3406-o3407

doi:10.1107/S1600536812046326

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N-(4-Fluorobenzoyl)-N′,N′′-diisopropylphosphoric triamide

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

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and ^bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
^*Correspondence e-mail: pourayoubi@um.ac.ir

(Received 6 November 2012; accepted 9 November 2012; online 24 November 2012)

The asymmetric unit of the title phosphoric triamide, C₁₃H₂₁FN₃O₂P, consists of two independent molecules. In each molecule, the P=O group and the N—H unit belonging to the C(O)NHP(O) fragment are in a syn conformation with respect to each other. An intramolecular N—H⋯O hydrogen bond occurs in each molecule. The P atom adopts a distorted tetrahedral environment. The methyl groups of an isopropyl fragment are disordered over two sets of sites with refined occupancies of 0.458 (5) and 0.542 (5). In the crystal, molecules are linked through N—H⋯O(=P) and N—H⋯O(=C) hydrogen bonds into chains along [001].

Related literature

For related structures with a [C(O)NH]P(O)[NHC]₂ moiety, see: Pourayoubi et al. (2011 ); Raissi Shabari et al. (2012 ). For the preparation of the starting compound 4-F—C₆H₄C(O)NHP(O)Cl₂, see: Tarahhomi et al. (2011 ).

Experimental

Crystal data

C₁₃H₂₁FN₃O₂P
M_r = 301.30
Monoclinic, P 2₁ /c
a = 15.9974 (12) Å
b = 10.7474 (7) Å
c = 19.5478 (13) Å
β = 111.461 (2)°
V = 3127.8 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.22 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.959, T_max = 0.972
24038 measured reflections
6366 independent reflections
4979 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.140
S = 1.08
6366 reflections
385 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.28 e Å⁻³
Δρ_min = −1.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4ⁱ	0.87 (2)	1.97 (2)	2.832 (2)	172 (2)
N2—H2N⋯O3ⁱⁱ	0.85 (2)	2.18 (2)	3.010 (2)	167 (2)
N3—H3N⋯O1	0.83 (2)	2.51 (3)	2.990 (3)	118 (2)
N4—H4N⋯O2ⁱⁱⁱ	0.85 (2)	1.96 (2)	2.802 (2)	171 (3)
N5—H5N⋯O1ⁱⁱ	0.85 (2)	2.15 (2)	2.990 (2)	167 (2)
N6—H6N⋯O3	0.83 (2)	2.51 (3)	3.055 (3)	124 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: Mercury (Macrae et al., 2008 ) and 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/S1600536812046326/ff2089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046326/ff2089Isup2.hkl

checkCIF report

Comment top

The structure determination of the title compound, [4-F—C₆H₄C(O)NH]P(O)[NHCH(CH₃)₂]₂ (Fig. 1), was performed as a part of a project on the synthesis of new phosphoric triamides with a [C(O)NH]P(O)[NHC]₂ skeleton (Pourayoubi et al., 2011; Raissi Shabari et al., 2012).

The asymmetric unit of the title compound consists of two independent molecules. In one molecule, disorder with respect to the methyl carbon atoms C12 and C13 of an isopropyl group was treated using a two-part model (45.8/54.2) with restrained C—C distances of 1.55 (0.02) Å.

In the C(O)NHP(O) fragment, the phosphoryl group adopts a syn orientation with respect to the N—H unit. The P atoms are in a distorted tetrahedral environment as has been noted for other phosphoric triamides (Pourayoubi et al., 2011). The P═O, C═O and P—N bond lengths and the P—N—C bond angles are within the expected values (Pourayoubi et al., 2011; Raissi Shabari et al., 2012).

In the crystal structure, the molecules are linked through N—H···O(═P) and N—H···O(═C) hydrogen bonds into chains along [001], giving R₂²(8) and R₂²(12) rings (Fig. 2). This sequence of ring motifs is similar to most of the phosphoric triamides with a [C(O)NH]P(O)[NHC]₂ skeleton (Pourayoubi et al., 2011). Moreover, two intramolecular N—H···O(═C) hydrogen bonds (Table 1) are found in the structure.

Related literature top

For related structures with a [C(O)NH]P(O)[NHC]₂ moiety, see: Pourayoubi et al. (2011); Raissi Shabari et al. (2012). For the preparation of the starting compound 4-F—C₆H₄C(O)NHP(O)Cl₂, see: Tarahhomi et al. (2011)

Experimental top

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

To a solution of 4-F—C₆H₄C(O)NHP(O)Cl₂ (1 mmol) in chloroform (25 ml), a solution of isopropylamine (4 mmol) in chloroform (5 ml) was added at 273 K. After 4 h stirring, the solvent was removed and the product was washed with distilled water and recrystallized from a mixture of CH₃OH/DMF (5:1 v/v) 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: Mercury (Macrae et al., 2008) and 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 and atom labeling scheme for the title compound. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii.

Fig. 2. Part of the crystal packing of the title compound via the N—H···O hydrogen bonds parallel to [001], building R₂²(8) and R₂²(12) rings. The intermolecular hydrogen bonds are shown as dotted lines and the H atoms not involved in hydrogen bonding have been omitted for the sake of clarity. The CH(CH₃)₂ substituents are shown as balls. The intramolecular N—H···O hydrogen bonds are not shown.

N-(4-Fluorobenzoyl)-N',N''-diisopropylphosphoric triamide top

Crystal data top

C₁₃H₂₁FN₃O₂P	F(000) = 1280
M_r = 301.30	D_x = 1.280 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.9974 (12) Å	Cell parameters from 6765 reflections
b = 10.7474 (7) Å	θ = 2.7–26.4°
c = 19.5478 (13) Å	µ = 0.19 mm⁻¹
β = 111.461 (2)°	T = 100 K
V = 3127.8 (4) Å³	Block, colourless
Z = 8	0.22 × 0.20 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	6366 independent reflections
Radiation source: fine-focus sealed tube	4979 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 26.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −20→19
T_min = 0.959, T_max = 0.972	k = −12→13
24038 measured reflections	l = −24→24

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0604P)² + 3.5857P] where P = (F_o² + 2F_c²)/3
6366 reflections	(Δ/σ)_max = 0.024
385 parameters	Δρ_max = 1.28 e Å⁻³
11 restraints	Δρ_min = −1.25 e Å⁻³

Crystal data top

C₁₃H₂₁FN₃O₂P	V = 3127.8 (4) Å³
M_r = 301.30	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.9974 (12) Å	µ = 0.19 mm⁻¹
b = 10.7474 (7) Å	T = 100 K
c = 19.5478 (13) Å	0.22 × 0.20 × 0.15 mm
β = 111.461 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6366 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4979 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.972	R_int = 0.035
24038 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	11 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 1.28 e Å⁻³
6366 reflections	Δρ_min = −1.25 e Å⁻³
385 parameters

Special details top

Experimental. IR (KBr, ν, cm^-1): 3345, 3095, 2972, 1657, 1452, 1291, 1215, 1139, 1025, 887, 769, 683.

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	0.66641 (4)	0.16703 (5)	0.60938 (3)	0.01446 (15)
P2	0.21362 (4)	0.66868 (5)	0.64779 (3)	0.01601 (15)
F1	1.19973 (10)	0.26579 (16)	0.81566 (8)	0.0353 (4)
F2	0.75090 (10)	0.72695 (16)	0.81958 (8)	0.0346 (4)
O1	0.81182 (11)	0.27790 (16)	0.57067 (9)	0.0233 (4)
O2	0.62755 (10)	0.11428 (15)	0.66103 (8)	0.0184 (3)
O3	0.34880 (12)	0.81368 (16)	0.60767 (9)	0.0257 (4)
O4	0.18241 (11)	0.59057 (15)	0.69603 (8)	0.0191 (3)
N1	0.77938 (13)	0.17148 (18)	0.65776 (10)	0.0167 (4)
H1N	0.7967 (17)	0.148 (2)	0.7034 (10)	0.020*
N2	0.64876 (13)	0.08672 (17)	0.53551 (10)	0.0163 (4)
H2N	0.6444 (17)	0.124 (2)	0.4962 (11)	0.020*
N3	0.63066 (14)	0.30688 (18)	0.58047 (11)	0.0199 (4)
H3N	0.6526 (18)	0.333 (2)	0.5509 (13)	0.024*
N4	0.32492 (13)	0.69042 (18)	0.69250 (10)	0.0182 (4)
H4N	0.3451 (17)	0.668 (2)	0.7372 (10)	0.022*
N5	0.19346 (14)	0.60247 (18)	0.56892 (10)	0.0190 (4)
H5N	0.1955 (18)	0.647 (2)	0.5336 (12)	0.023*
N6	0.17165 (14)	0.80866 (19)	0.63345 (11)	0.0225 (4)
H6N	0.2011 (18)	0.861 (2)	0.6202 (15)	0.027*
C1	0.98985 (16)	0.3212 (2)	0.66618 (13)	0.0214 (5)
H1B	0.9655	0.3738	0.6245	0.026*
C2	1.07965 (17)	0.3330 (2)	0.71090 (14)	0.0239 (5)
H2C	1.1172	0.3931	0.7009	0.029*
C3	1.11214 (16)	0.2545 (2)	0.77028 (13)	0.0240 (5)
C4	1.06095 (17)	0.1645 (2)	0.78636 (13)	0.0248 (5)
H4C	1.0865	0.1105	0.8272	0.030*
C5	0.97113 (16)	0.1547 (2)	0.74148 (12)	0.0204 (5)
H5B	0.9343	0.0940	0.7519	0.024*
C6	0.93470 (15)	0.2335 (2)	0.68126 (12)	0.0163 (4)
C7	0.83791 (15)	0.2292 (2)	0.63192 (12)	0.0174 (5)
C8	0.67839 (16)	−0.0441 (2)	0.54144 (13)	0.0216 (5)
H8A	0.6991	−0.0683	0.5944	0.026*
C9	0.75718 (18)	−0.0592 (3)	0.51657 (15)	0.0314 (6)
H9A	0.8062	−0.0041	0.5455	0.047*
H9B	0.7384	−0.0377	0.4644	0.047*
H9C	0.7779	−0.1458	0.5238	0.047*
C10	0.59970 (19)	−0.1273 (3)	0.49919 (16)	0.0339 (6)
H10A	0.5511	−0.1153	0.5178	0.051*
H10B	0.6190	−0.2145	0.5057	0.051*
H10C	0.5782	−0.1059	0.4469	0.051*
C11	0.62386 (19)	0.4006 (2)	0.63394 (14)	0.0293 (6)
H11A	0.6168	0.4687	0.5974	0.044*	0.458 (5)
H11B	0.6167	0.3669	0.6792	0.044*	0.542 (5)
C12	0.7119 (6)	0.4539 (9)	0.6829 (5)	0.0619 (11)	0.458 (5)
H12A	0.7376	0.4014	0.7266	0.093*	0.458 (5)
H12B	0.7026	0.5382	0.6978	0.093*	0.458 (5)
H12C	0.7532	0.4570	0.6562	0.093*	0.458 (5)
C13	0.5276 (6)	0.4168 (8)	0.6273 (5)	0.0619 (11)	0.458 (5)
H13A	0.4995	0.3349	0.6244	0.093*	0.458 (5)
H13B	0.4948	0.4644	0.5828	0.093*	0.458 (5)
H13C	0.5258	0.4615	0.6704	0.093*	0.458 (5)
C12'	0.6977 (5)	0.5009 (7)	0.6466 (5)	0.0619 (11)	0.542 (5)
H12D	0.7565	0.4650	0.6752	0.093*	0.542 (5)
H12E	0.6857	0.5712	0.6736	0.093*	0.542 (5)
H12F	0.6977	0.5299	0.5991	0.093*	0.542 (5)
C13'	0.5514 (5)	0.4973 (6)	0.5888 (4)	0.0619 (11)	0.542 (5)
H13D	0.4917	0.4590	0.5731	0.093*	0.542 (5)
H13E	0.5639	0.5235	0.5455	0.093*	0.542 (5)
H13F	0.5532	0.5700	0.6196	0.093*	0.542 (5)
C14	0.53551 (17)	0.8319 (2)	0.69340 (13)	0.0209 (5)
H14A	0.5109	0.8941	0.6570	0.025*
C15	0.62753 (17)	0.8276 (2)	0.73154 (14)	0.0245 (5)
H15A	0.6664	0.8872	0.7229	0.029*
C16	0.66076 (16)	0.7340 (2)	0.78238 (13)	0.0241 (5)
C17	0.60747 (17)	0.6462 (2)	0.79746 (13)	0.0248 (5)
H17A	0.6330	0.5823	0.8325	0.030*
C18	0.51529 (16)	0.6533 (2)	0.75999 (13)	0.0227 (5)
H18A	0.4770	0.5946	0.7701	0.027*
C19	0.47844 (16)	0.7459 (2)	0.70771 (12)	0.0179 (5)
C20	0.37995 (16)	0.7536 (2)	0.66527 (12)	0.0186 (5)
C21	0.20729 (17)	0.4683 (2)	0.56179 (13)	0.0232 (5)
H21A	0.2013	0.4257	0.6053	0.028*
C22	0.2994 (2)	0.4408 (3)	0.5623 (2)	0.0550 (9)
H22A	0.3444	0.4811	0.6049	0.082*
H22B	0.3046	0.4728	0.5171	0.082*
H22C	0.3093	0.3507	0.5652	0.082*
C23	0.1340 (3)	0.4201 (3)	0.4942 (2)	0.0723 (14)
H23A	0.0754	0.4378	0.4974	0.108*
H23B	0.1409	0.3300	0.4904	0.108*
H23C	0.1378	0.4610	0.4506	0.108*
C24	0.07352 (18)	0.8274 (2)	0.60296 (14)	0.0277 (6)
H24A	0.0453	0.7512	0.6145	0.033*
C25	0.0378 (2)	0.8417 (3)	0.52048 (15)	0.0354 (7)
H25A	0.0521	0.7670	0.4982	0.053*
H25B	0.0655	0.9145	0.5072	0.053*
H25C	−0.0275	0.8529	0.5025	0.053*
C26	0.0489 (2)	0.9359 (3)	0.64109 (16)	0.0430 (8)
H26A	0.0694	0.9193	0.6940	0.064*
H26B	−0.0165	0.9470	0.6214	0.064*
H26C	0.0777	1.0117	0.6326	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0147 (3)	0.0187 (3)	0.0103 (3)	−0.0003 (2)	0.0049 (2)	−0.0013 (2)
P2	0.0177 (3)	0.0191 (3)	0.0117 (3)	0.0005 (2)	0.0059 (2)	0.0002 (2)
F1	0.0164 (8)	0.0524 (10)	0.0328 (8)	−0.0072 (7)	0.0038 (6)	−0.0086 (7)
F2	0.0178 (8)	0.0483 (10)	0.0357 (9)	−0.0050 (7)	0.0076 (6)	−0.0064 (7)
O1	0.0236 (9)	0.0325 (9)	0.0150 (8)	−0.0006 (7)	0.0085 (7)	0.0053 (7)
O2	0.0179 (8)	0.0257 (8)	0.0128 (7)	−0.0031 (7)	0.0070 (6)	−0.0031 (6)
O3	0.0286 (10)	0.0303 (9)	0.0171 (8)	−0.0017 (7)	0.0072 (7)	0.0081 (7)
O4	0.0197 (9)	0.0259 (9)	0.0128 (7)	−0.0032 (7)	0.0070 (6)	−0.0004 (6)
N1	0.0157 (10)	0.0243 (10)	0.0096 (8)	−0.0030 (8)	0.0039 (7)	0.0006 (7)
N2	0.0196 (10)	0.0201 (10)	0.0086 (8)	0.0011 (8)	0.0044 (7)	0.0010 (7)
N3	0.0234 (11)	0.0206 (10)	0.0172 (10)	0.0028 (8)	0.0093 (8)	0.0005 (8)
N4	0.0191 (10)	0.0253 (10)	0.0097 (9)	−0.0015 (8)	0.0047 (7)	0.0034 (7)
N5	0.0265 (11)	0.0193 (10)	0.0123 (9)	0.0025 (8)	0.0084 (8)	0.0021 (7)
N6	0.0251 (12)	0.0198 (10)	0.0228 (10)	0.0026 (8)	0.0091 (9)	−0.0005 (8)
C1	0.0225 (13)	0.0202 (12)	0.0264 (12)	0.0010 (9)	0.0146 (10)	0.0008 (9)
C2	0.0213 (13)	0.0214 (12)	0.0341 (14)	−0.0048 (10)	0.0163 (11)	−0.0051 (10)
C3	0.0148 (12)	0.0341 (14)	0.0235 (12)	−0.0031 (10)	0.0076 (9)	−0.0100 (10)
C4	0.0206 (13)	0.0354 (14)	0.0178 (11)	0.0021 (11)	0.0063 (10)	0.0037 (10)
C5	0.0179 (12)	0.0259 (12)	0.0187 (11)	−0.0023 (9)	0.0082 (9)	0.0013 (9)
C6	0.0159 (11)	0.0201 (11)	0.0147 (10)	−0.0008 (9)	0.0079 (9)	−0.0025 (8)
C7	0.0201 (12)	0.0192 (11)	0.0152 (11)	−0.0008 (9)	0.0089 (9)	−0.0007 (9)
C8	0.0252 (13)	0.0219 (12)	0.0169 (11)	0.0032 (10)	0.0067 (9)	−0.0015 (9)
C9	0.0239 (14)	0.0318 (14)	0.0384 (15)	0.0035 (11)	0.0112 (12)	−0.0096 (12)
C10	0.0354 (16)	0.0271 (14)	0.0448 (17)	−0.0065 (12)	0.0215 (13)	−0.0123 (12)
C11	0.0413 (16)	0.0229 (13)	0.0277 (13)	0.0037 (11)	0.0173 (12)	−0.0055 (10)
C12	0.083 (3)	0.046 (2)	0.070 (3)	−0.003 (2)	0.044 (2)	−0.0214 (19)
C13	0.083 (3)	0.046 (2)	0.070 (3)	−0.003 (2)	0.044 (2)	−0.0214 (19)
C12'	0.083 (3)	0.046 (2)	0.070 (3)	−0.003 (2)	0.044 (2)	−0.0214 (19)
C13'	0.083 (3)	0.046 (2)	0.070 (3)	−0.003 (2)	0.044 (2)	−0.0214 (19)
C14	0.0285 (13)	0.0173 (11)	0.0218 (12)	−0.0018 (10)	0.0151 (10)	−0.0013 (9)
C15	0.0243 (13)	0.0227 (12)	0.0329 (13)	−0.0075 (10)	0.0179 (11)	−0.0054 (10)
C16	0.0173 (12)	0.0326 (13)	0.0232 (12)	−0.0034 (10)	0.0082 (10)	−0.0093 (10)
C17	0.0234 (13)	0.0334 (14)	0.0185 (11)	0.0007 (10)	0.0088 (10)	0.0034 (10)
C18	0.0214 (13)	0.0295 (13)	0.0183 (11)	−0.0033 (10)	0.0085 (10)	0.0041 (10)
C19	0.0225 (12)	0.0200 (11)	0.0139 (10)	−0.0019 (9)	0.0099 (9)	−0.0023 (8)
C20	0.0242 (13)	0.0186 (11)	0.0140 (10)	−0.0005 (9)	0.0081 (9)	−0.0002 (9)
C21	0.0321 (14)	0.0202 (12)	0.0188 (11)	0.0048 (10)	0.0111 (10)	−0.0010 (9)
C22	0.053 (2)	0.0428 (19)	0.080 (3)	0.0130 (16)	0.037 (2)	−0.0067 (18)
C23	0.061 (2)	0.0353 (18)	0.087 (3)	0.0087 (17)	−0.013 (2)	−0.0311 (19)
C24	0.0289 (14)	0.0278 (13)	0.0281 (13)	0.0090 (11)	0.0124 (11)	0.0041 (10)
C25	0.0352 (16)	0.0377 (15)	0.0277 (14)	0.0128 (12)	0.0048 (12)	0.0006 (12)
C26	0.053 (2)	0.0476 (18)	0.0314 (15)	0.0243 (15)	0.0183 (14)	0.0018 (13)

Geometric parameters (Å, º) top

P1—O2	1.4788 (16)	C11—C12'	1.551 (7)
P1—N2	1.6159 (18)	C11—C13'	1.567 (7)
P1—N3	1.634 (2)	C11—H11A	1.0000
P1—N1	1.7065 (19)	C11—H11B	1.0000
P2—O4	1.4792 (16)	C12—H12A	0.9800
P2—N5	1.6197 (19)	C12—H12B	0.9800
P2—N6	1.629 (2)	C12—H12C	0.9800
P2—N4	1.688 (2)	C13—H13A	0.9800
F1—C3	1.362 (3)	C13—H13B	0.9800
F2—C16	1.359 (3)	C13—H13C	0.9800
O1—C7	1.231 (3)	C12'—H12D	0.9800
O3—C20	1.234 (3)	C12'—H12E	0.9800
N1—C7	1.365 (3)	C12'—H12F	0.9800
N1—H1N	0.868 (16)	C13'—H13D	0.9800
N2—C8	1.475 (3)	C13'—H13E	0.9800
N2—H2N	0.848 (16)	C13'—H13F	0.9800
N3—C11	1.484 (3)	C14—C15	1.386 (4)
N3—H3N	0.828 (17)	C14—C19	1.397 (3)
N4—C20	1.364 (3)	C14—H14A	0.9500
N4—H4N	0.849 (17)	C15—C16	1.377 (4)
N5—C21	1.473 (3)	C15—H15A	0.9500
N5—H5N	0.852 (17)	C16—C17	1.374 (4)
N6—C24	1.475 (3)	C17—C18	1.388 (3)
N6—H6N	0.833 (17)	C17—H17A	0.9500
C1—C2	1.388 (3)	C18—C19	1.393 (3)
C1—C6	1.395 (3)	C18—H18A	0.9500
C1—H1B	0.9500	C19—C20	1.490 (3)
C2—C3	1.374 (4)	C21—C22	1.498 (4)
C2—H2C	0.9500	C21—C23	1.502 (4)
C3—C4	1.375 (4)	C21—H21A	1.0000
C4—C5	1.387 (3)	C22—H22A	0.9800
C4—H4C	0.9500	C22—H22B	0.9800
C5—C6	1.393 (3)	C22—H22C	0.9800
C5—H5B	0.9500	C23—H23A	0.9800
C6—C7	1.496 (3)	C23—H23B	0.9800
C8—C9	1.516 (4)	C23—H23C	0.9800
C8—C10	1.519 (4)	C24—C25	1.509 (4)
C8—H8A	1.0000	C24—C26	1.512 (4)
C9—H9A	0.9800	C24—H24A	1.0000
C9—H9B	0.9800	C25—H25A	0.9800
C9—H9C	0.9800	C25—H25B	0.9800
C10—H10A	0.9800	C25—H25C	0.9800
C10—H10B	0.9800	C26—H26A	0.9800
C10—H10C	0.9800	C26—H26B	0.9800
C11—C12	1.497 (9)	C26—H26C	0.9800
C11—C13	1.508 (8)

O2—P1—N2	115.19 (10)	C13—C11—H11B	71.0
O2—P1—N3	114.04 (10)	C12'—C11—H11B	116.0
N2—P1—N3	104.94 (10)	C13'—C11—H11B	116.0
O2—P1—N1	104.88 (9)	H11A—C11—H11B	151.4
N2—P1—N1	108.28 (10)	C11—C12—H12A	109.5
N3—P1—N1	109.37 (10)	C11—C12—H12B	109.5
O4—P2—N5	111.19 (10)	H12A—C12—H12B	109.5
O4—P2—N6	114.82 (10)	C11—C12—H12C	109.5
N5—P2—N6	108.42 (10)	H12A—C12—H12C	109.5
O4—P2—N4	106.65 (9)	H12B—C12—H12C	109.5
N5—P2—N4	111.01 (10)	C11—C13—H13A	109.5
N6—P2—N4	104.57 (11)	C11—C13—H13B	109.5
C7—N1—P1	122.57 (16)	H13A—C13—H13B	109.5
C7—N1—H1N	120.4 (17)	C11—C13—H13C	109.5
P1—N1—H1N	115.9 (17)	H13A—C13—H13C	109.5
C8—N2—P1	119.54 (15)	H13B—C13—H13C	109.5
C8—N2—H2N	116.2 (18)	C11—C12'—H12D	109.5
P1—N2—H2N	119.1 (18)	C11—C12'—H12E	109.5
C11—N3—P1	119.18 (16)	H12D—C12'—H12E	109.5
C11—N3—H3N	114.6 (19)	C11—C12'—H12F	109.5
P1—N3—H3N	112.0 (19)	H12D—C12'—H12F	109.5
C20—N4—P2	125.15 (16)	H12E—C12'—H12F	109.5
C20—N4—H4N	119.2 (18)	C11—C13'—H13D	109.5
P2—N4—H4N	115.2 (18)	C11—C13'—H13E	109.5
C21—N5—P2	122.39 (16)	H13D—C13'—H13E	109.5
C21—N5—H5N	115.1 (18)	C11—C13'—H13F	109.5
P2—N5—H5N	118.0 (18)	H13D—C13'—H13F	109.5
C24—N6—P2	120.41 (17)	H13E—C13'—H13F	109.5
C24—N6—H6N	115 (2)	C15—C14—C19	120.9 (2)
P2—N6—H6N	116 (2)	C15—C14—H14A	119.6
C2—C1—C6	121.2 (2)	C19—C14—H14A	119.6
C2—C1—H1B	119.4	C16—C15—C14	117.8 (2)
C6—C1—H1B	119.4	C16—C15—H15A	121.1
C3—C2—C1	117.4 (2)	C14—C15—H15A	121.1
C3—C2—H2C	121.3	F2—C16—C17	117.8 (2)
C1—C2—H2C	121.3	F2—C16—C15	118.7 (2)
F1—C3—C2	118.4 (2)	C17—C16—C15	123.4 (2)
F1—C3—C4	118.1 (2)	C16—C17—C18	118.1 (2)
C2—C3—C4	123.5 (2)	C16—C17—H17A	120.9
C3—C4—C5	118.3 (2)	C18—C17—H17A	120.9
C3—C4—H4C	120.8	C17—C18—C19	120.6 (2)
C5—C4—H4C	120.8	C17—C18—H18A	119.7
C4—C5—C6	120.3 (2)	C19—C18—H18A	119.7
C4—C5—H5B	119.8	C18—C19—C14	119.1 (2)
C6—C5—H5B	119.8	C18—C19—C20	121.7 (2)
C5—C6—C1	119.2 (2)	C14—C19—C20	119.2 (2)
C5—C6—C7	122.7 (2)	O3—C20—N4	120.9 (2)
C1—C6—C7	118.0 (2)	O3—C20—C19	121.9 (2)
O1—C7—N1	121.2 (2)	N4—C20—C19	117.19 (19)
O1—C7—C6	121.1 (2)	N5—C21—C22	111.9 (2)
N1—C7—C6	117.63 (19)	N5—C21—C23	109.0 (2)
N2—C8—C9	111.0 (2)	C22—C21—C23	112.8 (3)
N2—C8—C10	109.9 (2)	N5—C21—H21A	107.6
C9—C8—C10	112.5 (2)	C22—C21—H21A	107.6
N2—C8—H8A	107.7	C23—C21—H21A	107.6
C9—C8—H8A	107.7	C21—C22—H22A	109.5
C10—C8—H8A	107.7	C21—C22—H22B	109.5
C8—C9—H9A	109.5	H22A—C22—H22B	109.5
C8—C9—H9B	109.5	C21—C22—H22C	109.5
H9A—C9—H9B	109.5	H22A—C22—H22C	109.5
C8—C9—H9C	109.5	H22B—C22—H22C	109.5
H9A—C9—H9C	109.5	C21—C23—H23A	109.5
H9B—C9—H9C	109.5	C21—C23—H23B	109.5
C8—C10—H10A	109.5	H23A—C23—H23B	109.5
C8—C10—H10B	109.5	C21—C23—H23C	109.5
H10A—C10—H10B	109.5	H23A—C23—H23C	109.5
C8—C10—H10C	109.5	H23B—C23—H23C	109.5
H10A—C10—H10C	109.5	N6—C24—C25	112.2 (2)
H10B—C10—H10C	109.5	N6—C24—C26	109.7 (2)
N3—C11—C12	114.5 (4)	C25—C24—C26	112.5 (2)
N3—C11—C13	110.7 (4)	N6—C24—H24A	107.4
C12—C11—C13	134.7 (5)	C25—C24—H24A	107.4
N3—C11—C12'	109.7 (3)	C26—C24—H24A	107.4
C12—C11—C12'	31.6 (4)	C24—C25—H25A	109.5
C13—C11—C12'	129.0 (4)	C24—C25—H25B	109.5
N3—C11—C13'	106.5 (3)	H25A—C25—H25B	109.5
C12—C11—C13'	115.8 (5)	C24—C25—H25C	109.5
C13—C11—C13'	49.7 (4)	H25A—C25—H25C	109.5
C12'—C11—C13'	89.6 (4)	H25B—C25—H25C	109.5
N3—C11—H11A	90.6	C24—C26—H26A	109.5
C12—C11—H11A	90.6	C24—C26—H26B	109.5
C13—C11—H11A	90.6	H26A—C26—H26B	109.5
C12'—C11—H11A	59.1	C24—C26—H26C	109.5
C13'—C11—H11A	41.1	H26A—C26—H26C	109.5
N3—C11—H11B	116.0	H26B—C26—H26C	109.5
C12—C11—H11B	87.7

O2—P1—N1—C7	−171.46 (18)	C5—C6—C7—O1	−163.0 (2)
N2—P1—N1—C7	65.1 (2)	C1—C6—C7—O1	17.6 (3)
N3—P1—N1—C7	−48.8 (2)	C5—C6—C7—N1	18.1 (3)
O2—P1—N2—C8	−57.3 (2)	C1—C6—C7—N1	−161.2 (2)
N3—P1—N2—C8	176.46 (17)	P1—N2—C8—C9	−109.6 (2)
N1—P1—N2—C8	59.74 (19)	P1—N2—C8—C10	125.23 (19)
O2—P1—N3—C11	43.7 (2)	P1—N3—C11—C12	75.4 (5)
N2—P1—N3—C11	170.64 (18)	P1—N3—C11—C13	−102.8 (4)
N1—P1—N3—C11	−73.4 (2)	P1—N3—C11—C12'	109.2 (4)
O4—P2—N4—C20	177.25 (18)	P1—N3—C11—C13'	−155.2 (3)
N5—P2—N4—C20	56.0 (2)	C19—C14—C15—C16	1.7 (3)
N6—P2—N4—C20	−60.7 (2)	C14—C15—C16—F2	179.0 (2)
O4—P2—N5—C21	−41.3 (2)	C14—C15—C16—C17	−0.6 (4)
N6—P2—N5—C21	−168.44 (19)	F2—C16—C17—C18	179.6 (2)
N4—P2—N5—C21	77.2 (2)	C15—C16—C17—C18	−0.8 (4)
O4—P2—N6—C24	−56.2 (2)	C16—C17—C18—C19	1.1 (4)
N5—P2—N6—C24	68.8 (2)	C17—C18—C19—C14	0.0 (3)
N4—P2—N6—C24	−172.75 (17)	C17—C18—C19—C20	178.3 (2)
C6—C1—C2—C3	0.4 (3)	C15—C14—C19—C18	−1.4 (3)
C1—C2—C3—F1	−178.9 (2)	C15—C14—C19—C20	−179.8 (2)
C1—C2—C3—C4	1.2 (4)	P2—N4—C20—O3	9.1 (3)
F1—C3—C4—C5	178.3 (2)	P2—N4—C20—C19	−170.58 (16)
C2—C3—C4—C5	−1.8 (4)	C18—C19—C20—O3	−161.9 (2)
C3—C4—C5—C6	0.8 (4)	C14—C19—C20—O3	16.4 (3)
C4—C5—C6—C1	0.8 (3)	C18—C19—C20—N4	17.7 (3)
C4—C5—C6—C7	−178.6 (2)	C14—C19—C20—N4	−164.0 (2)
C2—C1—C6—C5	−1.4 (3)	P2—N5—C21—C22	−92.0 (3)
C2—C1—C6—C7	178.0 (2)	P2—N5—C21—C23	142.6 (3)
P1—N1—C7—O1	−2.4 (3)	P2—N6—C24—C25	−94.2 (2)
P1—N1—C7—C6	176.42 (15)	P2—N6—C24—C26	140.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4ⁱ	0.87 (2)	1.97 (2)	2.832 (2)	172 (2)
N2—H2N···O3ⁱⁱ	0.85 (2)	2.18 (2)	3.010 (2)	167 (2)
N3—H3N···O1	0.83 (2)	2.51 (3)	2.990 (3)	118 (2)
N4—H4N···O2ⁱⁱⁱ	0.85 (2)	1.96 (2)	2.802 (2)	171 (3)
N5—H5N···O1ⁱⁱ	0.85 (2)	2.15 (2)	2.990 (2)	167 (2)
N6—H6N···O3	0.83 (2)	2.51 (3)	3.055 (3)	124 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₂₁FN₃O₂P
M_r	301.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.9974 (12), 10.7474 (7), 19.5478 (13)
β (°)	111.461 (2)
V (Å³)	3127.8 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.22 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.959, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	24038, 6366, 4979
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.140, 1.08
No. of reflections	6366
No. of parameters	385
No. of restraints	11
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.28, −1.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008) and SHELXTL (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···O4ⁱ	0.868 (16)	1.970 (17)	2.832 (2)	172 (2)
N2—H2N···O3ⁱⁱ	0.848 (16)	2.177 (17)	3.010 (2)	167 (2)
N3—H3N···O1	0.828 (17)	2.51 (3)	2.990 (3)	118 (2)
N4—H4N···O2ⁱⁱⁱ	0.849 (17)	1.960 (17)	2.802 (2)	171 (3)
N5—H5N···O1ⁱⁱ	0.852 (17)	2.154 (18)	2.990 (2)	167 (2)
N6—H6N···O3	0.833 (17)	2.51 (3)	3.055 (3)	124 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2.

Acknowledgements

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

References

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