N-(3-Fluoro­benzo­yl)-N′,N′′-bis­(4-methyl­phen­yl)phospho­ric triamide

Pourayoubi, M.; Shoghpour, S.; Bruno, G.; Amiri Rudbari, H.

doi:10.1107/S1600536811045314

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3034

doi:10.1107/S1600536811045314

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N-(3-Fluorobenzoyl)-N′,N′′-bis(4-methylphenyl)phosphoric triamide

Mehrdad Pourayoubi,^a ^* Samad Shoghpour,^a Giuseppe Bruno ^b and Hadi Amiri Rudbari ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDipartimento di Chimica Inorganica, Villaggio S. Agata, Salita Sperone 31, Università di Messina, 98166 Messina, Italy
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 3 October 2011; accepted 17 October 2011; online 29 October 2011)

In the title compound, C₂₁H₂₁FN₃O₂P, the NH and P(=O) groups of the C(=O)NHP(=O) fragment are in a syn arrangement with respect to each other, as are the two amide H atoms of the two CH₃–4-C₆H₄–NH moieties. In the crystal, molecules are linked through N—H⋯O(=P) and N—H⋯O(=C) hydrogen bonds, forming R₂²(8) and R₂²(12) rings, which are arranged in chains parallel to [010].

Related literature

For hydrogen-bond patterns in phosphoric triamides of the formula RC(O)NHP(O)[NR¹R²]₂ and RC(O)NHP(O)[NHR¹]₂, see: Toghraee et al. (2011 ). For different cyclic hydrogen-bond motifs, see: Pourayoubi et al. (2011 ).

Experimental

Crystal data

C₂₁H₂₁FN₃O₂P
M_r = 397.38
Monoclinic, P 2₁ /n
a = 10.2132 (5) Å
b = 9.8588 (4) Å
c = 20.2711 (9) Å
β = 93.621 (2)°
V = 2037.02 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 296 K
0.25 × 0.22 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.662, T_max = 0.745
20105 measured reflections
3844 independent reflections
3061 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.04
3844 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	1.97	2.7835 (18)	157
N3—H3⋯O1ⁱⁱ	0.86	2.06	2.8972 (18)	165
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX (Dolomanov et al., 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811045314/lh5349sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811045314/lh5349Isup2.hkl

checkCIF report

Comment top

The possible hydrogen bond patterns in crystal structure of phosphoric triamides of the general formula RC(O)NHP(O)[NR¹R²]₂ and RC(O)NHP(O)[NHR¹]₂ have been analyzed recently (Toghraee et al., 2011) and the hydrogen bonds strengths in these systems were discussed based on cyclic hydrogen bond motifs (Pourayoubi et al., 2011). It was concluded that the R₂²(8) ring motif is generated by a pair of P(═O)···H–N_C(O)NHP(O) hydrogen bonds between two neighboring molecules in the crystal packing of phosphoric triamides of the formula RC(O)NHP(O)[NR¹R²]₂ which contain a syn orientation of P(═O) versus N—H. In the case of phosphoric triamides of the formula RC(O)NHP(O)[NHR¹]₂, crystal structure is usually composed of a chain of R₂²(8) and R₂²(12) ring motifs which alternately connected to each other. However, a few other hydrogen bond patterns were also found. The R₂²(8) motif is formed by two P(═O)···H–N_C(O)NHP(O) hydrogen bonds and the R₂²(12) motif by two C(═O)···H–N_amide hydrogen bonds. In this work, the synthesis and crystal structure of a new phosphoric triamide, P(O)[NHC(O)C₆H₄(3-F)][NH–C₆H₄–4–CH₃]₂, is reported. This investigation was carried out as part of a comprehensive study on the hydrogen bonds pattern in phosphoric triamides with formula RC(O)NHP(O)[NHR¹]₂. The phosphorus atom has a distorted tetrahedral environment (Fig. 1). Comparison of the O–P–N angles indicates that the O–P–N1 angle is smaller than ideal tetrahedral (107.02 (7)°) and the O–P–N2 and O–P–N3 angles (113.75 (7)° and 116.29 (7)°, respectively) display larger than ideal values. This probably arises due to steric repulsion involving the P(═O) group. Moreover, there is no π···π interaction between the two para-methyl phenyl groups. The C(═O) and P(═O) groups of the C(═O)NHP(═O) moiety are in anti positions relative to each other, contrary to the syn orientation of P(═O) and NH groups. The P(═O), C(═O) and P–N bond lengths and P–N–C bond angles are in the range of the expected values. In the crystal structure, molecules are linked through P(═O)···H–N_C(O)NHP(O) and C(═ O)···H–N_amide hydrogen bonds (Table 1), to give a linear chain running along the b axis.

Related literature top

For hydrogen-bond patterns in phosphoric triamides of the formula RC(O)NHP(O)[NR¹R²]₂ and RC(O)NHP(O)[NHR¹]₂, see: Toghraee et al. (2011). For different cyclic hydrogen-bond motifs, see: Pourayoubi et al. (2011).

Experimental top

Synthesis of 3-F–C₆H₄C(O)NHP(O)Cl₂ A mixture of phosphorus pentachloride (3.773 g, 18.12 mmol) and 3-fluorobenzamide (2.521 g, 18.12 mmol) were refluxed in CCl₄ for 8 h, and then the resulting solution was cooled to the room temperature. Formic acid (0.834 g, 18.12 mmol) was syringed dropwise into the stirring solution in 20 min and stirred for 6 h to yield the white precipitate that was filtered and dried in vacuum.

Synthesis of the title molecule To a solution of 3-F–C₆H₄C(O)NHP(O)Cl₂ (0.256 g, 1 mmol) in CHCl₃ (20 ml), a mixture of p-toluidine (0.214 g, 2 mmol) and triethylamine (0.202 g, 2 mmol) in CHCl₃ (5 ml) was added dropwise at 273 K. After 4 h stirring, the solvent was evaporated in vacuum and then the resulting solid was washed with distilled water. Single crystals of title compound were obtained from a mixture of CH₃OH, CH₃CN and n-C₆H₁₄ after slow evaporation at room temperature. IR (KBr, cm^-1): 3355 (NH), 3313 (NH), 3081 (NH), 2921, 1651 (C═O), 1615, 1588, 1513, 1440, 1386, 1267, 1235, 1210, 961, 870, 861, 817, 751.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX (Dolomanov et al., 2003); 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. Ellipsoids are given at the 50% probability level.

N-(3-Fluorobenzoyl)-N',N''-bis(4-methylphenyl)phosphoric triamide top

Crystal data top

C₂₁H₂₁FN₃O₂P	F(000) = 832
M_r = 397.38	D_x = 1.296 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6910 reflections
a = 10.2132 (5) Å	θ = 2.3–25.1°
b = 9.8588 (4) Å	µ = 0.17 mm⁻¹
c = 20.2711 (9) Å	T = 296 K
β = 93.621 (2)°	Cubic, colorless
V = 2037.02 (16) Å³	0.25 × 0.22 × 0.14 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3844 independent reflections
Radiation source: fine-focus sealed tube	3061 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.7°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
T_min = 0.662, T_max = 0.745	k = −12→11
20105 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0537P)² + 0.6292P] where P = (F_o² + 2F_c²)/3
3844 reflections	(Δ/σ)_max = 0.003
255 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₁H₂₁FN₃O₂P	V = 2037.02 (16) Å³
M_r = 397.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.2132 (5) Å	µ = 0.17 mm⁻¹
b = 9.8588 (4) Å	T = 296 K
c = 20.2711 (9) Å	0.25 × 0.22 × 0.14 mm
β = 93.621 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3844 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3061 reflections with I > 2σ(I)
T_min = 0.662, T_max = 0.745	R_int = 0.030
20105 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	Δρ_max = 0.37 e Å⁻³
3844 reflections	Δρ_min = −0.35 e Å⁻³
255 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.55273 (4)	0.28199 (4)	0.97803 (2)	0.03501 (15)
F1	0.00592 (13)	0.50210 (15)	1.10740 (8)	0.0863 (5)
O1	0.32311 (13)	0.10156 (12)	0.97315 (7)	0.0522 (4)
O2	0.62121 (12)	0.41249 (11)	0.97696 (6)	0.0424 (3)
N1	0.39319 (14)	0.31600 (13)	0.98654 (7)	0.0384 (4)
H1	0.3699	0.3994	0.9901	0.046*
N2	0.56968 (16)	0.18952 (15)	0.91224 (7)	0.0457 (4)
H2	0.5594	0.1032	0.9149	0.055*
N3	0.59807 (15)	0.17934 (14)	1.03822 (7)	0.0407 (4)
H3	0.6244	0.1001	1.0273	0.049*
C1	0.0244 (2)	0.3949 (2)	1.06744 (11)	0.0523 (5)
C2	0.14869 (18)	0.36985 (19)	1.04838 (10)	0.0462 (5)
H2A	0.2185	0.4259	1.0621	0.055*
C3	0.16722 (17)	0.25899 (17)	1.00822 (9)	0.0381 (4)
C4	0.29931 (18)	0.21885 (16)	0.98807 (9)	0.0375 (4)
C5	0.60112 (19)	0.24700 (18)	0.85011 (9)	0.0439 (4)
C6	0.7180 (2)	0.3164 (2)	0.84531 (11)	0.0558 (5)
H6	0.7763	0.3256	0.8822	0.067*
C7	0.7477 (3)	0.3719 (3)	0.78558 (12)	0.0684 (7)
H7	0.8258	0.4196	0.7831	0.082*
C8	0.6657 (3)	0.3589 (2)	0.72965 (11)	0.0726 (7)
C9	0.7009 (4)	0.4217 (3)	0.66478 (14)	0.1173 (13)
H9A	0.7807	0.3818	0.6512	0.176*
H9B	0.7130	0.5176	0.6705	0.176*
H9C	0.6314	0.4053	0.6316	0.176*
C10	0.06158 (19)	0.1775 (2)	0.98825 (10)	0.0492 (5)
H10	0.0741	0.1025	0.9616	0.059*
C11	−0.0622 (2)	0.2074 (2)	1.00776 (12)	0.0601 (6)
H11	−0.1329	0.1531	0.9936	0.072*
C12	−0.0815 (2)	0.3170 (2)	1.04808 (12)	0.0591 (6)
H12	−0.1645	0.3374	1.0617	0.071*
C13	0.59854 (18)	0.20754 (18)	1.10666 (9)	0.0410 (4)
C14	0.6514 (2)	0.1138 (2)	1.15103 (10)	0.0577 (5)
H14	0.6853	0.0331	1.1357	0.069*
C15	0.6545 (3)	0.1384 (3)	1.21817 (12)	0.0753 (7)
H15	0.6903	0.0735	1.2473	0.090*
C16	0.6059 (3)	0.2569 (3)	1.24288 (11)	0.0699 (7)
C17	0.5550 (3)	0.3505 (3)	1.19855 (12)	0.0721 (7)
H17	0.5225	0.4317	1.2142	0.087*
C18	0.5505 (2)	0.3279 (2)	1.13088 (11)	0.0609 (6)
H18	0.5154	0.3933	1.1019	0.073*
C19	0.6086 (4)	0.2837 (4)	1.31697 (12)	0.1036 (11)
H19A	0.6172	0.3794	1.3250	0.155*
H19B	0.6818	0.2370	1.3386	0.155*
H19C	0.5286	0.2517	1.3340	0.155*
C20	0.5180 (2)	0.2333 (2)	0.79481 (11)	0.0633 (6)
H20	0.4392	0.1869	0.7974	0.076*
C21	0.5505 (3)	0.2879 (3)	0.73502 (11)	0.0772 (8)
H21	0.4936	0.2766	0.6978	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0371 (3)	0.0248 (2)	0.0440 (3)	0.00215 (18)	0.00981 (19)	−0.00342 (18)
F1	0.0618 (9)	0.0742 (9)	0.1262 (13)	0.0042 (7)	0.0322 (8)	−0.0372 (9)
O1	0.0543 (8)	0.0277 (6)	0.0757 (9)	−0.0005 (6)	0.0121 (7)	−0.0088 (6)
O2	0.0414 (7)	0.0284 (6)	0.0589 (8)	−0.0007 (5)	0.0146 (6)	−0.0053 (6)
N1	0.0370 (8)	0.0245 (7)	0.0543 (9)	0.0032 (6)	0.0083 (7)	−0.0023 (6)
N2	0.0605 (10)	0.0281 (7)	0.0503 (9)	−0.0020 (7)	0.0171 (8)	−0.0054 (7)
N3	0.0478 (9)	0.0273 (7)	0.0477 (9)	0.0088 (6)	0.0078 (7)	−0.0044 (6)
C1	0.0467 (11)	0.0432 (11)	0.0681 (13)	0.0050 (9)	0.0131 (10)	−0.0026 (10)
C2	0.0386 (10)	0.0372 (10)	0.0634 (12)	−0.0022 (8)	0.0082 (9)	−0.0043 (9)
C3	0.0394 (10)	0.0312 (8)	0.0441 (10)	−0.0004 (7)	0.0050 (8)	0.0047 (7)
C4	0.0427 (10)	0.0277 (8)	0.0424 (9)	−0.0009 (7)	0.0040 (8)	−0.0001 (7)
C5	0.0524 (11)	0.0362 (9)	0.0443 (10)	0.0017 (8)	0.0137 (9)	−0.0071 (8)
C6	0.0523 (12)	0.0636 (13)	0.0527 (12)	−0.0067 (10)	0.0117 (10)	−0.0048 (10)
C7	0.0773 (16)	0.0674 (15)	0.0634 (15)	−0.0214 (13)	0.0275 (13)	−0.0077 (12)
C8	0.113 (2)	0.0568 (13)	0.0499 (13)	−0.0161 (14)	0.0230 (14)	−0.0076 (11)
C9	0.200 (4)	0.098 (2)	0.0569 (16)	−0.045 (3)	0.036 (2)	0.0000 (16)
C10	0.0486 (12)	0.0433 (10)	0.0556 (12)	−0.0079 (9)	0.0027 (9)	−0.0022 (9)
C11	0.0420 (12)	0.0631 (14)	0.0747 (15)	−0.0108 (10)	−0.0004 (10)	0.0009 (12)
C12	0.0368 (11)	0.0619 (13)	0.0796 (15)	0.0015 (10)	0.0108 (10)	0.0076 (12)
C13	0.0419 (10)	0.0363 (9)	0.0450 (10)	−0.0035 (8)	0.0052 (8)	−0.0018 (8)
C14	0.0731 (15)	0.0432 (11)	0.0556 (13)	0.0021 (10)	−0.0059 (11)	0.0006 (9)
C15	0.110 (2)	0.0598 (14)	0.0541 (14)	−0.0110 (14)	−0.0124 (13)	0.0081 (12)
C16	0.0890 (18)	0.0740 (16)	0.0471 (12)	−0.0304 (14)	0.0079 (12)	−0.0068 (12)
C17	0.0956 (19)	0.0633 (14)	0.0590 (14)	−0.0005 (14)	0.0174 (13)	−0.0187 (12)
C18	0.0824 (16)	0.0496 (12)	0.0512 (12)	0.0142 (11)	0.0073 (11)	−0.0072 (10)
C19	0.148 (3)	0.116 (2)	0.0475 (14)	−0.048 (2)	0.0094 (16)	−0.0108 (15)
C20	0.0697 (15)	0.0617 (14)	0.0588 (13)	−0.0191 (12)	0.0068 (11)	−0.0095 (11)
C21	0.107 (2)	0.0759 (17)	0.0473 (13)	−0.0201 (16)	−0.0021 (13)	−0.0073 (12)

Geometric parameters (Å, º) top

P1—O2	1.4652 (12)	C9—H9A	0.9600
P1—N3	1.6297 (15)	C9—H9B	0.9600
P1—N2	1.6336 (15)	C9—H9C	0.9600
P1—N1	1.6830 (14)	C10—C11	1.380 (3)
F1—C1	1.352 (2)	C10—H10	0.9300
O1—C4	1.224 (2)	C11—C12	1.377 (3)
N1—C4	1.357 (2)	C11—H11	0.9300
N1—H1	0.8600	C12—H12	0.9300
N2—C5	1.436 (2)	C13—C14	1.376 (3)
N2—H2	0.8600	C13—C18	1.386 (3)
N3—C13	1.415 (2)	C14—C15	1.381 (3)
N3—H3	0.8600	C14—H14	0.9300
C1—C12	1.364 (3)	C15—C16	1.376 (4)
C1—C2	1.373 (3)	C15—H15	0.9300
C2—C3	1.383 (3)	C16—C17	1.367 (4)
C2—H2A	0.9300	C16—C19	1.523 (3)
C3—C10	1.385 (3)	C17—C18	1.388 (3)
C3—C4	1.488 (2)	C17—H17	0.9300
C5—C20	1.369 (3)	C18—H18	0.9300
C5—C6	1.385 (3)	C19—H19A	0.9600
C6—C7	1.380 (3)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C8	1.373 (4)	C20—C21	1.386 (3)
C7—H7	0.9300	C20—H20	0.9300
C8—C21	1.378 (4)	C21—H21	0.9300
C8—C9	1.517 (3)

O2—P1—N3	116.29 (8)	C8—C9—H9C	109.5
O2—P1—N2	113.75 (7)	H9A—C9—H9C	109.5
N3—P1—N2	103.00 (8)	H9B—C9—H9C	109.5
O2—P1—N1	107.02 (7)	C11—C10—C3	120.22 (19)
N3—P1—N1	106.15 (7)	C11—C10—H10	119.9
N2—P1—N1	110.37 (8)	C3—C10—H10	119.9
C4—N1—P1	123.49 (12)	C12—C11—C10	120.4 (2)
C4—N1—H1	118.3	C12—C11—H11	119.8
P1—N1—H1	118.3	C10—C11—H11	119.8
C5—N2—P1	122.47 (12)	C1—C12—C11	118.13 (19)
C5—N2—H2	118.8	C1—C12—H12	120.9
P1—N2—H2	118.8	C11—C12—H12	120.9
C13—N3—P1	126.55 (12)	C14—C13—C18	118.45 (19)
C13—N3—H3	116.7	C14—C13—N3	119.09 (17)
P1—N3—H3	116.7	C18—C13—N3	122.44 (17)
F1—C1—C12	118.31 (18)	C13—C14—C15	120.7 (2)
F1—C1—C2	118.40 (19)	C13—C14—H14	119.7
C12—C1—C2	123.3 (2)	C15—C14—H14	119.7
C1—C2—C3	118.11 (18)	C16—C15—C14	121.4 (2)
C1—C2—H2A	120.9	C16—C15—H15	119.3
C3—C2—H2A	120.9	C14—C15—H15	119.3
C2—C3—C10	119.83 (17)	C17—C16—C15	117.7 (2)
C2—C3—C4	122.14 (16)	C17—C16—C19	120.9 (3)
C10—C3—C4	117.95 (16)	C15—C16—C19	121.4 (3)
O1—C4—N1	120.64 (16)	C16—C17—C18	121.9 (2)
O1—C4—C3	121.13 (16)	C16—C17—H17	119.0
N1—C4—C3	118.22 (14)	C18—C17—H17	119.0
C20—C5—C6	118.93 (19)	C13—C18—C17	119.8 (2)
C20—C5—N2	121.18 (18)	C13—C18—H18	120.1
C6—C5—N2	119.89 (18)	C17—C18—H18	120.1
C7—C6—C5	119.7 (2)	C16—C19—H19A	109.5
C7—C6—H6	120.1	C16—C19—H19B	109.5
C5—C6—H6	120.1	H19A—C19—H19B	109.5
C8—C7—C6	122.1 (2)	C16—C19—H19C	109.5
C8—C7—H7	119.0	H19A—C19—H19C	109.5
C6—C7—H7	119.0	H19B—C19—H19C	109.5
C7—C8—C21	117.5 (2)	C5—C20—C21	120.5 (2)
C7—C8—C9	120.8 (3)	C5—C20—H20	119.8
C21—C8—C9	121.7 (3)	C21—C20—H20	119.8
C8—C9—H9A	109.5	C8—C21—C20	121.3 (2)
C8—C9—H9B	109.5	C8—C21—H21	119.4
H9A—C9—H9B	109.5	C20—C21—H21	119.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.97	2.7835 (18)	157
N3—H3···O1ⁱⁱ	0.86	2.06	2.8972 (18)	165

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁FN₃O₂P
M_r	397.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.2132 (5), 9.8588 (4), 20.2711 (9)
β (°)	93.621 (2)
V (Å³)	2037.02 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.25 × 0.22 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.662, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	20105, 3844, 3061
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.04
No. of reflections	3844
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.35

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX (Dolomanov et al., 2003), 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—H1···O2ⁱ	0.86	1.97	2.7835 (18)	157.0
N3—H3···O1ⁱⁱ	0.86	2.06	2.8972 (18)	164.6

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

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
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Blake, A. J., Champness, N. R. & Schröder, M. (2003). J. Appl. Cryst. 36, 1283–1284. Web of Science CrossRef CAS 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
Toghraee, M., Pourayoubi, M. & Divjakovic, V. (2011). Polyhedron, 30, 1680–1690. Web of Science CSD CrossRef CAS Google Scholar