N-(2-Fluoro­benzo­yl)-N′,N′′-bis­(4-methyl­phen­yl)phospho­ric triamide

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

doi:10.1107/S1600536811009640

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o934

doi:10.1107/S1600536811009640

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N-(2-Fluorobenzoyl)-N′,N′′-bis(4-methylphenyl)phosphoric 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 13 February 2011; accepted 14 March 2011; online 19 March 2011)

The P atom in the title compound, C₂₁H₂₁FN₃O₂P, is in a tetrahedral coordination environment and the environment of each N atom is essentially planar (sums of angles = 359.7, 359.9 and 358.4°). The phosphoryl and carbonyl groups adopt anti orientations with respect to each other. In the crystal, adjacent molecules are linked via N—H⋯O=P and two N—H⋯O=C hydrogen bonds into an extended chain parallel to the a axis.

Related literature

For a phosphorus ligand having a C(O)NHP(O) skeleton, see: Gholivand et al. (2010 ). For a related structure, see: Pourayoubi et al. (2010 ). For bond lengths in related structures, see: Sabbaghi et al. (2010 ) and references cited therein.

Experimental

Crystal data

C₂₁H₂₁FN₃O₂P
M_r = 397.38
Monoclinic, P 2₁ /n
a = 9.7697 (9) Å
b = 10.2197 (9) Å
c = 20.2404 (18) Å
β = 96.605 (1)°
V = 2007.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.959, T_max = 0.975
15865 measured reflections
4551 independent reflections
3411 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.127
S = 1.05
4551 reflections
264 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.87 (1)	1.92 (1)	2.780 (2)	171 (2)
N2—H2N⋯O1ⁱⁱ	0.86 (1)	2.08 (1)	2.886 (2)	156 (2)
N3—H3N⋯O1ⁱⁱ	0.86 (1)	2.24 (2)	2.945 (2)	139 (2)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+2, -z+1.

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/S1600536811009640/nc2222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009640/nc2222Isup2.hkl

checkCIF report

Comment top

Carbacylamidophosphates with a C(O)NHP(O) skeleton have attracted attention because of their roles as the O,O'-donor ligands for metal complexation (Gholivand et al., 2010). Following the previous works about carbacylamidophosphates such as P(O)[NHC(O)C₆H₃(2,6-F₂)][N(CH₃)(CH₂C₆H₅)]₂ (Pourayoubi et al., 2010), here, we report on the synthesis and crystal structure of the title compound, P(O)[NHC(O)C₆H₄(2-F)][NH—C₆H₄-4-CH₃]₂.

In the crystal structure of the title compound the phosphoryl and carbonyl groups adopt anti positions to each other. The P atom has a slightly distorted tetrahedral configuration (Fig. 1). The bond angles around the P atom are in the range of 101.09 (8)° to 116.67 (8)°. The P1—N2 and P1—N3 bonds (1.6361 (15) Å and 1.6291 (17) Å) are shorter than the P1—N1 bond (1.6872 (15) Å). The environment of the nitrogen atoms is essentially planar. The P═O bond length of 1.4723 (13) Å is comparable to those in similar compounds e.g. in P(O)[NHC(O)C₆H₄(4-NO₂)][NHC₆H₁₁]₂ (Sabbaghi et al., 2010).

In the crystal structure, adjacent molecules are linked via N_C(O)NHP(O)—H···O ═P and two N_amide—H···O ═C hydrogen bonds (see Table 1), into an extended chain parallel to the a axis.

Related literature top

For a phosphorus ligand having a C(O)NHP(O) skeleton, see: Gholivand et al. (2010). For a related structure, see: Pourayoubi et al. (2010). For bond lengths in related structures, see: Sabbaghi et al. (2010) and references cited therein.

Experimental top

2-F—C₆H₄C(O)NHP(O)Cl₂ has been synthesized from the reaction between phosphorus pentachloride (4.0 g, 19.2 mmol) and 2-fluorobenzamide (2.671 g, 19.2 mmol) in dry CCl₄ at 358 K (3 h) and then the treatment of formic acid (0.884 g, 19.2 mmol) at ice bath temperature. To a solution of 2-F—C₆H₄C(O)NHP(O)Cl₂ (0.3 g, 1.17 mmol) in dry chloroform (30 ml), a mixture of p-toluidine (0.251 g, 2.34 mmol) and triethylamine (0.237 g, 2.34 mmol) in dry chloroform (10 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 methanol/chloroform at room temperature. IR (KBr, cm^-1): 3308 (NH), 3030 (NH), 2896, 2627, 1639 (C═O), 1457, 1220, 1061, 944, 795.

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 of title compound with labeling. Displacement ellipsoids are drawn at the 50% probability level.

N-{bis[(4-methylphenyl)amino]phosphoryl}-2-fluorobenzamide top

Crystal data top

C₂₁H₂₁FN₃O₂P	F(000) = 832
M_r = 397.38	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7697 (9) Å	Cell parameters from 5744 reflections
b = 10.2197 (9) Å	θ = 2.2–27.5°
c = 20.2404 (18) Å	µ = 0.17 mm⁻¹
β = 96.605 (1)°	T = 100 K
V = 2007.5 (3) Å³	Block, colourless
Z = 4	0.25 × 0.15 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4551 independent reflections
Radiation source: fine-focus sealed tube	3411 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.959, T_max = 0.975	k = −11→13
15865 measured reflections	l = −25→25

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0669P)² + 0.498P] where P = (F_o² + 2F_c²)/3
4551 reflections	(Δ/σ)_max = 0.007
264 parameters	Δρ_max = 0.41 e Å⁻³
3 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₁H₂₁FN₃O₂P	V = 2007.5 (3) Å³
M_r = 397.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7697 (9) Å	µ = 0.17 mm⁻¹
b = 10.2197 (9) Å	T = 100 K
c = 20.2404 (18) Å	0.25 × 0.15 × 0.15 mm
β = 96.605 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4551 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3411 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.975	R_int = 0.035
15865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	3 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.41 e Å⁻³
4551 reflections	Δρ_min = −0.26 e Å⁻³
264 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
P1	0.72255 (5)	0.92119 (4)	0.50855 (2)	0.02136 (14)
F1	0.92737 (14)	1.40039 (12)	0.55287 (6)	0.0441 (3)
O1	0.91560 (13)	1.14443 (13)	0.50431 (6)	0.0293 (3)
O2	0.58757 (12)	0.86140 (12)	0.51487 (6)	0.0250 (3)
N1	0.69300 (16)	1.08365 (14)	0.50258 (7)	0.0210 (3)
H1N	0.6074 (11)	1.1095 (19)	0.4983 (9)	0.025*
N2	0.79772 (16)	0.87866 (15)	0.44363 (8)	0.0240 (3)
H2N	0.8811 (12)	0.8507 (19)	0.4525 (10)	0.029*
N3	0.84260 (16)	0.88686 (16)	0.56874 (8)	0.0267 (4)
H3N	0.9270 (12)	0.905 (2)	0.5636 (10)	0.032*
C1	0.8139 (2)	1.41838 (19)	0.50898 (9)	0.0296 (4)
C2	0.7701 (2)	1.5451 (2)	0.49516 (11)	0.0381 (5)
H2C	0.8194	1.6173	0.5157	0.046*
C3	0.6533 (2)	1.5647 (2)	0.45090 (11)	0.0379 (5)
H3B	0.6219	1.6511	0.4408	0.045*
C4	0.5822 (2)	1.4596 (2)	0.42132 (11)	0.0344 (5)
H4A	0.5029	1.4737	0.3903	0.041*
C5	0.6265 (2)	1.33331 (19)	0.43680 (9)	0.0278 (4)
H5A	0.5765	1.2612	0.4166	0.033*
C6	0.74372 (19)	1.31052 (17)	0.48164 (9)	0.0230 (4)
C7	0.79305 (18)	1.17460 (18)	0.49728 (8)	0.0220 (4)
C8	0.7441 (2)	0.89104 (17)	0.37612 (9)	0.0244 (4)
C9	0.6203 (2)	0.9545 (2)	0.35614 (10)	0.0319 (5)
H9A	0.5685	0.9914	0.3884	0.038*
C10	0.5725 (2)	0.9640 (2)	0.28921 (10)	0.0360 (5)
H10A	0.4886	1.0089	0.2762	0.043*
C11	0.6439 (2)	0.9096 (2)	0.24070 (10)	0.0404 (5)
C12	0.7657 (2)	0.8443 (2)	0.26118 (10)	0.0419 (6)
H12A	0.8157	0.8051	0.2288	0.050*
C13	0.8164 (2)	0.8347 (2)	0.32801 (10)	0.0341 (5)
H13A	0.9004	0.7898	0.3409	0.041*
C14	0.5884 (3)	0.9202 (3)	0.16774 (11)	0.0561 (7)
H14A	0.6098	0.8398	0.1446	0.084*
H14B	0.6313	0.9950	0.1479	0.084*
H14C	0.4884	0.9326	0.1636	0.084*
C15	0.8269 (2)	0.85706 (18)	0.63606 (9)	0.0260 (4)
C16	0.7217 (2)	0.7756 (2)	0.65213 (10)	0.0406 (5)
H16A	0.6570	0.7408	0.6180	0.049*
C17	0.7115 (2)	0.7452 (3)	0.71817 (11)	0.0506 (7)
H17A	0.6367	0.6929	0.7288	0.061*
C18	0.8072 (3)	0.7891 (2)	0.76906 (10)	0.0435 (6)
C19	0.9162 (3)	0.8633 (2)	0.75138 (11)	0.0507 (7)
H19A	0.9862	0.8909	0.7850	0.061*
C20	0.9253 (3)	0.8980 (2)	0.68584 (11)	0.0427 (6)
H20A	1.0000	0.9504	0.6752	0.051*
C21	0.7964 (3)	0.7510 (3)	0.84055 (11)	0.0657 (8)
H21A	0.8791	0.7801	0.8687	0.099*
H21B	0.7879	0.6557	0.8437	0.099*
H21C	0.7150	0.7926	0.8556	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0143 (3)	0.0263 (2)	0.0236 (2)	0.00103 (18)	0.00229 (18)	0.00314 (18)
F1	0.0442 (8)	0.0440 (7)	0.0404 (7)	−0.0137 (6)	−0.0116 (6)	−0.0023 (5)
O1	0.0150 (7)	0.0379 (8)	0.0351 (8)	−0.0004 (6)	0.0030 (6)	0.0005 (6)
O2	0.0142 (7)	0.0278 (7)	0.0330 (7)	−0.0001 (5)	0.0025 (5)	0.0038 (5)
N1	0.0143 (8)	0.0244 (8)	0.0245 (8)	0.0002 (6)	0.0038 (6)	0.0007 (6)
N2	0.0158 (8)	0.0297 (8)	0.0262 (8)	0.0048 (6)	0.0015 (6)	−0.0003 (6)
N3	0.0133 (8)	0.0388 (9)	0.0279 (9)	0.0000 (7)	0.0018 (7)	0.0086 (6)
C1	0.0288 (11)	0.0346 (11)	0.0252 (10)	−0.0079 (9)	0.0024 (8)	−0.0004 (8)
C2	0.0497 (15)	0.0292 (10)	0.0368 (12)	−0.0104 (10)	0.0106 (10)	−0.0051 (9)
C3	0.0433 (14)	0.0280 (11)	0.0443 (12)	0.0005 (9)	0.0135 (11)	0.0062 (9)
C4	0.0271 (11)	0.0353 (11)	0.0411 (12)	0.0002 (9)	0.0058 (9)	0.0084 (9)
C5	0.0231 (10)	0.0292 (10)	0.0317 (10)	−0.0033 (8)	0.0057 (8)	0.0011 (8)
C6	0.0202 (10)	0.0273 (9)	0.0227 (9)	−0.0035 (7)	0.0073 (7)	−0.0015 (7)
C7	0.0167 (10)	0.0303 (9)	0.0192 (9)	−0.0013 (7)	0.0033 (7)	−0.0019 (7)
C8	0.0212 (10)	0.0274 (9)	0.0247 (9)	−0.0034 (8)	0.0032 (8)	0.0010 (7)
C9	0.0270 (11)	0.0404 (11)	0.0278 (10)	0.0020 (9)	0.0019 (8)	−0.0030 (8)
C10	0.0290 (12)	0.0461 (12)	0.0313 (11)	0.0001 (10)	−0.0038 (9)	0.0029 (9)
C11	0.0345 (13)	0.0601 (15)	0.0262 (11)	−0.0110 (11)	0.0015 (9)	0.0024 (9)
C12	0.0351 (13)	0.0624 (15)	0.0300 (12)	−0.0047 (11)	0.0109 (10)	−0.0062 (10)
C13	0.0254 (11)	0.0452 (12)	0.0324 (11)	0.0013 (9)	0.0060 (9)	−0.0017 (9)
C14	0.0465 (16)	0.095 (2)	0.0262 (12)	−0.0108 (14)	0.0008 (11)	0.0069 (12)
C15	0.0234 (10)	0.0299 (10)	0.0248 (10)	0.0057 (8)	0.0040 (8)	0.0025 (7)
C16	0.0266 (12)	0.0627 (15)	0.0318 (11)	−0.0063 (10)	0.0001 (9)	0.0129 (10)
C17	0.0322 (13)	0.0782 (18)	0.0421 (14)	−0.0019 (12)	0.0075 (11)	0.0229 (12)
C18	0.0496 (15)	0.0558 (14)	0.0263 (11)	0.0136 (12)	0.0098 (10)	0.0039 (9)
C19	0.0709 (19)	0.0504 (14)	0.0284 (12)	−0.0100 (13)	−0.0048 (12)	−0.0038 (10)
C20	0.0499 (15)	0.0433 (13)	0.0336 (12)	−0.0166 (11)	−0.0006 (10)	0.0005 (9)
C21	0.074 (2)	0.095 (2)	0.0310 (13)	0.0190 (17)	0.0163 (13)	0.0111 (13)

Geometric parameters (Å, º) top

P1—O2	1.4723 (13)	C9—H9A	0.9500
P1—N3	1.6291 (17)	C10—C11	1.385 (3)
P1—N2	1.6361 (15)	C10—H10A	0.9500
P1—N1	1.6872 (15)	C11—C12	1.386 (3)
F1—C1	1.351 (2)	C11—C14	1.517 (3)
O1—C7	1.229 (2)	C12—C13	1.389 (3)
N1—C7	1.362 (2)	C12—H12A	0.9500
N1—H1N	0.872 (9)	C13—H13A	0.9500
N2—C8	1.412 (2)	C14—H14A	0.9800
N2—H2N	0.862 (9)	C14—H14B	0.9800
N3—C15	1.422 (2)	C14—H14C	0.9800
N3—H3N	0.863 (9)	C15—C20	1.375 (3)
C1—C6	1.380 (3)	C15—C16	1.390 (3)
C1—C2	1.382 (3)	C16—C17	1.387 (3)
C2—C3	1.382 (3)	C16—H16A	0.9500
C2—H2C	0.9500	C17—C18	1.384 (3)
C3—C4	1.378 (3)	C17—H17A	0.9500
C3—H3B	0.9500	C18—C19	1.387 (3)
C4—C5	1.385 (3)	C18—C21	1.514 (3)
C4—H4A	0.9500	C19—C20	1.386 (3)
C5—C6	1.396 (3)	C19—H19A	0.9500
C5—H5A	0.9500	C20—H20A	0.9500
C6—C7	1.492 (3)	C21—H21A	0.9800
C8—C9	1.391 (3)	C21—H21B	0.9800
C8—C13	1.392 (3)	C21—H21C	0.9800
C9—C10	1.384 (3)

O2—P1—N3	114.88 (8)	C9—C10—C11	121.7 (2)
O2—P1—N2	116.67 (8)	C9—C10—H10A	119.2
N3—P1—N2	101.09 (8)	C11—C10—H10A	119.2
O2—P1—N1	105.49 (8)	C10—C11—C12	117.8 (2)
N3—P1—N1	111.59 (8)	C10—C11—C14	120.6 (2)
N2—P1—N1	107.03 (8)	C12—C11—C14	121.6 (2)
C7—N1—P1	123.97 (13)	C11—C12—C13	121.5 (2)
C7—N1—H1N	118.3 (13)	C11—C12—H12A	119.2
P1—N1—H1N	117.4 (13)	C13—C12—H12A	119.2
C8—N2—P1	127.06 (13)	C12—C13—C8	120.0 (2)
C8—N2—H2N	117.9 (13)	C12—C13—H13A	120.0
P1—N2—H2N	114.9 (13)	C8—C13—H13A	120.0
C15—N3—P1	127.97 (13)	C11—C14—H14A	109.5
C15—N3—H3N	111.7 (14)	C11—C14—H14B	109.5
P1—N3—H3N	118.7 (14)	H14A—C14—H14B	109.5
F1—C1—C6	119.15 (18)	C11—C14—H14C	109.5
F1—C1—C2	118.14 (18)	H14A—C14—H14C	109.5
C6—C1—C2	122.7 (2)	H14B—C14—H14C	109.5
C3—C2—C1	118.7 (2)	C20—C15—C16	118.94 (18)
C3—C2—H2C	120.7	C20—C15—N3	119.60 (18)
C1—C2—H2C	120.7	C16—C15—N3	121.11 (18)
C4—C3—C2	120.4 (2)	C17—C16—C15	119.8 (2)
C4—C3—H3B	119.8	C17—C16—H16A	120.1
C2—C3—H3B	119.8	C15—C16—H16A	120.1
C3—C4—C5	119.9 (2)	C18—C17—C16	121.8 (2)
C3—C4—H4A	120.0	C18—C17—H17A	119.1
C5—C4—H4A	120.0	C16—C17—H17A	119.1
C4—C5—C6	120.93 (19)	C17—C18—C19	117.3 (2)
C4—C5—H5A	119.5	C17—C18—C21	120.8 (2)
C6—C5—H5A	119.5	C19—C18—C21	121.8 (2)
C1—C6—C5	117.37 (18)	C20—C19—C18	121.5 (2)
C1—C6—C7	121.68 (18)	C20—C19—H19A	119.2
C5—C6—C7	120.92 (16)	C18—C19—H19A	119.2
O1—C7—N1	121.22 (17)	C15—C20—C19	120.5 (2)
O1—C7—C6	123.01 (16)	C15—C20—H20A	119.8
N1—C7—C6	115.77 (15)	C19—C20—H20A	119.8
C9—C8—C13	118.93 (18)	C18—C21—H21A	109.5
C9—C8—N2	122.47 (16)	C18—C21—H21B	109.5
C13—C8—N2	118.58 (17)	H21A—C21—H21B	109.5
C10—C9—C8	120.08 (18)	C18—C21—H21C	109.5
C10—C9—H9A	120.0	H21A—C21—H21C	109.5
C8—C9—H9A	120.0	H21B—C21—H21C	109.5

O2—P1—N1—C7	178.66 (14)	C5—C6—C7—N1	−39.0 (2)
N3—P1—N1—C7	53.27 (16)	P1—N2—C8—C9	6.1 (3)
N2—P1—N1—C7	−56.46 (16)	P1—N2—C8—C13	−172.26 (15)
O2—P1—N2—C8	57.27 (18)	C13—C8—C9—C10	−1.7 (3)
N3—P1—N2—C8	−177.42 (15)	N2—C8—C9—C10	179.93 (18)
N1—P1—N2—C8	−60.53 (17)	C8—C9—C10—C11	1.1 (3)
O2—P1—N3—C15	−28.7 (2)	C9—C10—C11—C12	0.3 (3)
N2—P1—N3—C15	−155.21 (16)	C9—C10—C11—C14	179.3 (2)
N1—P1—N3—C15	91.30 (17)	C10—C11—C12—C13	−0.9 (3)
F1—C1—C2—C3	−179.31 (17)	C14—C11—C12—C13	180.0 (2)
C6—C1—C2—C3	−1.7 (3)	C11—C12—C13—C8	0.3 (3)
C1—C2—C3—C4	0.1 (3)	C9—C8—C13—C12	1.0 (3)
C2—C3—C4—C5	1.1 (3)	N2—C8—C13—C12	179.47 (19)
C3—C4—C5—C6	−0.7 (3)	P1—N3—C15—C20	−144.91 (18)
F1—C1—C6—C5	179.64 (15)	P1—N3—C15—C16	41.9 (3)
C2—C1—C6—C5	2.0 (3)	C20—C15—C16—C17	4.9 (3)
F1—C1—C6—C7	−2.4 (3)	N3—C15—C16—C17	178.1 (2)
C2—C1—C6—C7	179.95 (17)	C15—C16—C17—C18	−3.0 (4)
C4—C5—C6—C1	−0.8 (3)	C16—C17—C18—C19	−1.2 (4)
C4—C5—C6—C7	−178.77 (17)	C16—C17—C18—C21	−178.0 (2)
P1—N1—C7—O1	−8.6 (2)	C17—C18—C19—C20	3.3 (4)
P1—N1—C7—C6	170.55 (12)	C21—C18—C19—C20	−179.9 (2)
C1—C6—C7—O1	−37.7 (3)	C16—C15—C20—C19	−2.8 (3)
C5—C6—C7—O1	140.17 (18)	N3—C15—C20—C19	−176.1 (2)
C1—C6—C7—N1	143.13 (17)	C18—C19—C20—C15	−1.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.87 (1)	1.92 (1)	2.780 (2)	171 (2)
N2—H2N···O1ⁱⁱ	0.86 (1)	2.08 (1)	2.886 (2)	156 (2)
N3—H3N···O1ⁱⁱ	0.86 (1)	2.24 (2)	2.945 (2)	139 (2)

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁FN₃O₂P
M_r	397.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.7697 (9), 10.2197 (9), 20.2404 (18)
β (°)	96.605 (1)
V (Å³)	2007.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.25 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.959, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	15865, 4551, 3411
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.127, 1.05
No. of reflections	4551
No. of parameters	264
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.26

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	0.872 (9)	1.916 (10)	2.780 (2)	171.0 (19)
N2—H2N···O1ⁱⁱ	0.862 (9)	2.077 (12)	2.886 (2)	156.1 (19)
N3—H3N···O1ⁱⁱ	0.863 (9)	2.236 (15)	2.945 (2)	139.3 (18)

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

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged. The authors wish to thank Bruker AXS Inc. for the use of one of their SMART X2S benchtop instruments.

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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