N,N′-Dibenzyl-N′′-(2,4-difluoro­benzo­yl)-N,N′-dimethyl­phospho­ric triamide

Pourayoubi, M.; Shoghpour, S.; Torre-Fernández, L.; García-Granda, S.

doi:10.1107/S1600536811055115

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o270-o271

doi:10.1107/S1600536811055115

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N,N′-Dibenzyl-N′′-(2,4-difluorobenzoyl)-N,N′-dimethylphosphoric triamide

Mehrdad Pourayoubi,^a Samad Shoghpour,^a Laura Torre-Fernández ^b and Santiago García-Granda ^b ^*

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDepartamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo – CINN, C/ Julián Clavería, 8, 33006 Oviedo, Asturias, Spain
^*Correspondence e-mail: sgg@uniovi.es

(Received 25 November 2011; accepted 21 December 2011; online 7 January 2012)

In the title molecule, C₂₃H₂₄F₂N₃O₂P, the P atom is in a distorted tetrahedral P(=O)(N)(N)₂ environment, with the bond angles around the P atom in the range 106.78 (11)–114.10 (13)°. The phosphoryl and carbonyl groups, which are separated by an N atom, adopt an anti orientation relative to each other. In the C(=O)NHP(=O) fragment, the P—N bond is longer [1.683 (2) Å] and the O—P—N angle is smaller [106.78 (11)°] than the other P—N bonds [1.613 (2) and 1.632 (2) Å] and O—P—N bond angles [114.10 (13) and 110.83 (12)°], respectively. The N atoms have sp² character. In the crystal, pairs of P=O⋯H—N hydrogen bonds form inversion dimers with R₂²(8) ring motifs.

Related literature

For hydrogen-bond patterns in compounds with formula RC(O)NHP(O)[NR¹R²]₂ and RC(O)NHP(O)[NHR¹]₂ and for the discussion of different C(=O) versus P(=O) orientations in the C(O)NHP(O) fragment, see: Toghraee et al. (2011 ). For hydrogen-bond strengths in cyclic hydrogen-bond motifs and for bond lengths and angles, see: Pourayoubi et al. (2011 ). For graph-set analysis of hydrogen-bonds motifs, see: Bernstein et al. (1995 ). For the synthesis of the starting phosphorous–chlorine compound, see: Pourayoubi et al. (2010 ).

Experimental

Crystal data

C₂₃H₂₄F₂N₃O₂P
M_r = 443.42
Triclinic, $[P \overline 1]$
a = 10.3619 (6) Å
b = 10.7721 (10) Å
c = 11.6433 (8) Å
α = 70.523 (7)°
β = 72.495 (5)°
γ = 70.197 (7)°
V = 1126.65 (15) Å³
Z = 2
Cu Kα radiation
μ = 1.44 mm⁻¹
T = 300 K
0.17 × 0.14 × 0.03 mm

Data collection

Agilent Xcalibur Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.954, T_max = 1.000
10022 measured reflections
4209 independent reflections
2758 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.141
S = 1.01
4209 reflections
268 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5ⁱ	0.86	1.96	2.812 (3)	171
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811055115/fy2035sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055115/fy2035Isup2.hkl

checkCIF report

Comment top

In a recently published paper, the collective behavior of hydrogen bonds (HBs) in the crystal packing of phosphoramidates having a C(═O)NHP(═O)(N)₂ and C(═O)NHP(═O)(NH)₂ skeletons were considered (Toghraee et al., 2011). The authors attempted to arrive at some empirical rules which are useful for predicting hydrogen-bond patterns in systems having "two H-acceptors and one H-donor site" and "two H-acceptors and three H-donor sites". As a continuation, the hydrogen bond strengths in such systems were analyzed based on hydrogen bond motifs (Pourayoubi et al., 2011).

The structure determination of the title molecule, P(O)[NHC(O)C₆H₃(2,4-F₂)][N(CH₃)(CH₂C₆H₅)]₂ (Fig. 1), was performed according to our interest in the collection of structural data related to new compounds having a C(O)NHP(O) skeleton.

The phosphoryl and the carbonyl groups in the title molecule adopt an anti orientation relative to each other similarly to most of the carbacylamidophosphates. However, a few examples with a gauche orientation of these two groups were also reported (Toghraee et al., 2011). The phosphorus atom has a distorted tetrahedral configuration and the P═O, C═O, P—N bond lengths and P—N—C bond angles are within the expected values. In the crystal structure, pairs of intermolecular P═ O···H—N hydrogen bonds (Table 1) form centrosymmetric dimers, see Figure 2, as R₂²(8) rings (Bernstein et al., 1995).

Related literature top

For hydrogen-bond patterns in compounds with formula RC(O)NHP(O)[NR¹R²]₂ and RC(O)NHP(O)[NHR¹]₂ and for the discussion of different C(═O) versus P(═O) orientations in the C(O)NHP(O) fragment, see: Toghraee et al. (2011). For hydrogen-bond strengths in cyclic hydrogen-bond motifs and for bond lengths and angles, see: Pourayoubi et al. (2011). For graph-set analysis of hydrogen-bonds motifs, see: Bernstein et al. (1995). For the synthesis of the starting phosphorous–chlorine compound, see: Pourayoubi et al. (2010).

Experimental top

Synthesis of 2,4-F₂–C₆H₃C(O)NHP(O)Cl₂. 2,4-F₂–C₆H₃C(O)NHP(O)Cl₂ was prepared similarly to the procedure which was used for the preparation of 2,6-F₂–C₆H₃C(O)NHP(O)Cl₂ (Pourayoubi et al., 2010), but by using 2,4–F₂–C₆H₃C(O)NH₂ instead of 2,6–F₂–C₆H₃C(O)NH₂.

Synthesis of title molecule. To a solution of 2,4-F₂–C₆H₃C(O)NHP(O)Cl₂ (2 mmol) in CHCl₃ (20 ml), a solution of N-methylbenzylamine (8 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 CHCl₃ and n-C₇H₁₆ (5 to 1 v/v) after slow evaporation at room temperature. IR (KBr, cm^-1): 3064, 3043, 2872, 1683 (C═O), 1615, 1453, 1343, 1265, 1215, 1175, 1155, 1128, 1088, 1017, 959, 877, 820, 791, 738, 714.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 30% probability level.
	Fig. 2. A view of the centrosymmetric dimer formed by H-bonding. The H atoms not involved in the hydrogen bonding interaction have been omitted for clarity.

N,N'-Dibenzyl-N''-(2,4-difluorobenzoyl)- N,N'-dimethylphosphoric triamide top

Crystal data top

C₂₃H₂₄F₂N₃O₂P	Z = 2
M_r = 443.42	F(000) = 464
Triclinic, P1	D_x = 1.307 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 10.3619 (6) Å	Cell parameters from 2755 reflections
b = 10.7721 (10) Å	θ = 4.1–70.6°
c = 11.6433 (8) Å	µ = 1.44 mm⁻¹
α = 70.523 (7)°	T = 300 K
β = 72.495 (5)°	Plate, colorless
γ = 70.197 (7)°	0.17 × 0.14 × 0.03 mm
V = 1126.65 (15) Å³

Data collection top

Agilent Xcalibur Gemini R diffractometer	4209 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2758 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 10.2673 pixels mm^-1	θ_max = 70.7°, θ_min = 4.1°
ω scans	h = −8→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→13
T_min = 0.954, T_max = 1.000	l = −14→14
10022 measured reflections

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) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0585P)²] where P = (F_o² + 2F_c²)/3
4209 reflections	(Δ/σ)_max < 0.001
268 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₃H₂₄F₂N₃O₂P	γ = 70.197 (7)°
M_r = 443.42	V = 1126.65 (15) Å³
Triclinic, P1	Z = 2
a = 10.3619 (6) Å	Cu Kα radiation
b = 10.7721 (10) Å	µ = 1.44 mm⁻¹
c = 11.6433 (8) Å	T = 300 K
α = 70.523 (7)°	0.17 × 0.14 × 0.03 mm
β = 72.495 (5)°

Data collection top

Agilent Xcalibur Gemini R diffractometer	4209 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2758 reflections with I > 2σ(I)
T_min = 0.954, T_max = 1.000	R_int = 0.044
10022 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	Δρ_max = 0.47 e Å⁻³
4209 reflections	Δρ_min = −0.27 e Å⁻³
268 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	0.58022 (6)	0.27216 (7)	0.57829 (7)	0.0460 (2)
N2	0.4103 (2)	0.3411 (2)	0.5698 (2)	0.0484 (5)
H2	0.3866	0.4255	0.5297	0.058*
N3	0.6579 (2)	0.1967 (3)	0.4676 (2)	0.0586 (6)
N4	0.5904 (2)	0.1570 (2)	0.7108 (2)	0.0528 (6)
O5	0.63610 (18)	0.38484 (19)	0.5704 (2)	0.0595 (5)
O6	0.3324 (2)	0.1512 (2)	0.6516 (2)	0.0684 (6)
F7	0.0748 (2)	0.2082 (2)	0.5985 (2)	0.0946 (7)
F8	−0.24562 (18)	0.6018 (2)	0.6907 (2)	0.0991 (7)
C9	0.1600 (3)	0.3630 (3)	0.6399 (3)	0.0503 (7)
C10	0.1264 (3)	0.4859 (3)	0.6711 (3)	0.0594 (7)
H10	0.1977	0.5144	0.6792	0.071*
C11	−0.0098 (3)	0.5667 (4)	0.6902 (3)	0.0681 (6)
H11	−0.0315	0.6484	0.7115	0.082*
C12	−0.1121 (3)	0.5211 (4)	0.6763 (3)	0.0681 (6)
C13	−0.0871 (3)	0.4028 (3)	0.6477 (3)	0.0604 (5)
H13	−0.1592	0.3749	0.6400	0.072*
C14	0.0492 (3)	0.3252 (3)	0.6305 (3)	0.0604 (5)
C15	0.6261 (3)	0.2312 (3)	0.2566 (3)	0.0548 (7)
C16	0.5939 (3)	0.3719 (3)	0.2161 (3)	0.0689 (9)
H16	0.5505	0.4238	0.2739	0.083*
C17	0.6249 (4)	0.4357 (4)	0.0925 (4)	0.0835 (11)
H17	0.6024	0.5305	0.0666	0.100*
C18	0.6890 (4)	0.3607 (5)	0.0060 (4)	0.0868 (12)
H18	0.7097	0.4047	−0.0783	0.104*
C19	0.7225 (3)	0.2209 (4)	0.0442 (3)	0.0767 (10)
H19	0.7663	0.1699	−0.0142	0.092*
C20	0.6910 (3)	0.1556 (3)	0.1697 (3)	0.0586 (7)
H20	0.7135	0.0607	0.1954	0.070*
C21	0.7259 (3)	−0.0736 (3)	0.8050 (3)	0.0553 (7)
C22	0.7176 (3)	−0.2009 (3)	0.8816 (3)	0.0663 (8)
H22	0.6435	−0.2339	0.8862	0.080*
C23	0.8165 (4)	−0.2796 (4)	0.9508 (4)	0.0905 (12)
H23	0.8101	−0.3658	1.0010	0.109*
C24	0.9252 (4)	−0.2314 (5)	0.9463 (4)	0.1019 (14)
H24	0.9920	−0.2843	0.9940	0.122*
C25	0.9347 (4)	−0.1054 (5)	0.8716 (4)	0.0970 (13)
H25	1.0080	−0.0723	0.8690	0.116*
C26	0.8370 (3)	−0.0268 (4)	0.8002 (4)	0.0770 (10)
H26	0.8456	0.0582	0.7484	0.092*
C27	0.3063 (3)	0.2749 (3)	0.6210 (3)	0.0512 (7)
C28	0.5913 (3)	0.1608 (3)	0.3930 (3)	0.0622 (8)
H28A	0.4903	0.1859	0.4229	0.075*
H28B	0.6220	0.0627	0.4037	0.075*
C29	0.6160 (3)	0.0108 (3)	0.7288 (3)	0.0600 (8)
H29A	0.6461	−0.0092	0.6481	0.072*
H29B	0.5289	−0.0148	0.7704	0.072*
C30	0.8121 (3)	0.1484 (4)	0.4424 (4)	0.0864 (12)
H30A	0.8473	0.1766	0.4943	0.130*
H30B	0.8494	0.1865	0.3563	0.130*
H30C	0.8401	0.0505	0.4600	0.130*
C31	0.5236 (4)	0.2029 (4)	0.8241 (3)	0.0922 (13)
H31A	0.5110	0.2996	0.8052	0.138*
H31B	0.5819	0.1564	0.8842	0.138*
H31C	0.4340	0.1831	0.8575	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0399 (3)	0.0435 (4)	0.0562 (4)	−0.0113 (3)	−0.0114 (3)	−0.0136 (3)
N2	0.0407 (10)	0.0409 (12)	0.0630 (15)	−0.0116 (9)	−0.0131 (10)	−0.0100 (10)
N3	0.0524 (12)	0.0660 (16)	0.0568 (15)	−0.0061 (11)	−0.0139 (11)	−0.0230 (12)
N4	0.0536 (12)	0.0533 (14)	0.0517 (14)	−0.0087 (10)	−0.0142 (11)	−0.0167 (11)
O5	0.0465 (9)	0.0476 (11)	0.0894 (15)	−0.0148 (8)	−0.0206 (10)	−0.0161 (10)
O6	0.0572 (11)	0.0446 (12)	0.1014 (18)	−0.0157 (9)	−0.0223 (11)	−0.0092 (11)
F7	0.0756 (12)	0.0788 (14)	0.150 (2)	−0.0270 (10)	−0.0354 (13)	−0.0388 (14)
F8	0.0412 (9)	0.1202 (18)	0.1219 (19)	−0.0012 (10)	−0.0078 (10)	−0.0427 (15)
C9	0.0430 (13)	0.0523 (16)	0.0551 (17)	−0.0172 (12)	−0.0112 (12)	−0.0079 (13)
C10	0.0503 (15)	0.0680 (19)	0.065 (2)	−0.0196 (14)	−0.0077 (13)	−0.0238 (16)
C11	0.0461 (10)	0.0789 (16)	0.0738 (16)	−0.0124 (10)	−0.0027 (10)	−0.0261 (13)
C12	0.0461 (10)	0.0789 (16)	0.0738 (16)	−0.0124 (10)	−0.0027 (10)	−0.0261 (13)
C13	0.0479 (9)	0.0677 (13)	0.0672 (14)	−0.0239 (9)	−0.0129 (9)	−0.0101 (11)
C14	0.0479 (9)	0.0677 (13)	0.0672 (14)	−0.0239 (9)	−0.0129 (9)	−0.0101 (11)
C15	0.0556 (15)	0.0624 (18)	0.0538 (18)	−0.0246 (13)	−0.0113 (13)	−0.0154 (14)
C16	0.076 (2)	0.063 (2)	0.067 (2)	−0.0164 (16)	−0.0143 (17)	−0.0183 (17)
C17	0.088 (2)	0.077 (2)	0.070 (2)	−0.018 (2)	−0.022 (2)	0.002 (2)
C18	0.081 (2)	0.110 (3)	0.056 (2)	−0.025 (2)	−0.0169 (18)	−0.002 (2)
C19	0.0647 (19)	0.109 (3)	0.062 (2)	−0.0185 (19)	−0.0110 (16)	−0.036 (2)
C20	0.0537 (15)	0.071 (2)	0.0576 (19)	−0.0199 (14)	−0.0103 (14)	−0.0230 (16)
C21	0.0517 (15)	0.0591 (17)	0.0504 (17)	−0.0104 (13)	−0.0117 (13)	−0.0117 (14)
C22	0.0624 (17)	0.0610 (19)	0.064 (2)	−0.0105 (15)	−0.0121 (15)	−0.0088 (16)
C23	0.085 (3)	0.079 (3)	0.079 (3)	−0.004 (2)	−0.024 (2)	0.003 (2)
C24	0.072 (2)	0.113 (4)	0.095 (3)	0.013 (2)	−0.038 (2)	−0.014 (3)
C25	0.0576 (19)	0.119 (4)	0.112 (3)	−0.012 (2)	−0.036 (2)	−0.022 (3)
C26	0.0608 (18)	0.082 (2)	0.084 (3)	−0.0206 (17)	−0.0262 (17)	−0.005 (2)
C27	0.0479 (14)	0.0464 (16)	0.0629 (18)	−0.0154 (12)	−0.0173 (13)	−0.0107 (13)
C28	0.0791 (19)	0.0574 (18)	0.0570 (19)	−0.0301 (15)	−0.0025 (15)	−0.0216 (15)
C29	0.0641 (17)	0.0502 (17)	0.068 (2)	−0.0211 (14)	−0.0254 (15)	−0.0026 (15)
C30	0.0557 (18)	0.109 (3)	0.083 (3)	0.0049 (18)	−0.0099 (17)	−0.042 (2)
C31	0.098 (3)	0.105 (3)	0.059 (2)	0.006 (2)	−0.019 (2)	−0.034 (2)

Geometric parameters (Å, º) top

P1—O5	1.4787 (19)	C17—H17	0.9300
P1—N3	1.613 (2)	C18—C19	1.371 (5)
P1—N4	1.632 (2)	C18—H18	0.9300
P1—N2	1.683 (2)	C19—C20	1.386 (5)
N2—C27	1.370 (3)	C19—H19	0.9300
N2—H2	0.8600	C20—H20	0.9300
N3—C28	1.465 (4)	C21—C22	1.379 (4)
N3—C30	1.472 (4)	C21—C26	1.385 (4)
N4—C31	1.455 (4)	C21—C29	1.510 (4)
N4—C29	1.458 (4)	C22—C23	1.367 (5)
O6—C27	1.213 (3)	C22—H22	0.9300
F7—C14	1.351 (4)	C23—C24	1.372 (6)
F8—C12	1.357 (3)	C23—H23	0.9300
C9—C14	1.385 (4)	C24—C25	1.364 (6)
C9—C10	1.392 (4)	C24—H24	0.9300
C9—C27	1.487 (4)	C25—C26	1.375 (5)
C10—C11	1.381 (4)	C25—H25	0.9300
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.379 (5)	C28—H28A	0.9700
C11—H11	0.9300	C28—H28B	0.9700
C12—C13	1.345 (4)	C29—H29A	0.9700
C13—C14	1.370 (4)	C29—H29B	0.9700
C13—H13	0.9300	C30—H30A	0.9600
C15—C16	1.381 (4)	C30—H30B	0.9600
C15—C20	1.382 (4)	C30—H30C	0.9600
C15—C28	1.504 (4)	C31—H31A	0.9600
C16—C17	1.363 (5)	C31—H31B	0.9600
C16—H16	0.9300	C31—H31C	0.9600
C17—C18	1.373 (6)

O5—P1—N3	114.10 (13)	C15—C20—C19	120.1 (3)
O5—P1—N4	110.83 (12)	C15—C20—H20	120.0
N3—P1—N4	108.04 (13)	C19—C20—H20	120.0
O5—P1—N2	106.78 (11)	C22—C21—C26	118.3 (3)
N3—P1—N2	108.02 (12)	C22—C21—C29	120.1 (3)
N4—P1—N2	108.93 (12)	C26—C21—C29	121.7 (3)
C27—N2—P1	125.86 (19)	C23—C22—C21	121.1 (3)
C27—N2—H2	117.1	C23—C22—H22	119.4
P1—N2—H2	117.1	C21—C22—H22	119.4
C28—N3—C30	114.7 (2)	C22—C23—C24	120.1 (4)
C28—N3—P1	127.0 (2)	C22—C23—H23	120.0
C30—N3—P1	118.1 (2)	C24—C23—H23	120.0
C31—N4—C29	114.2 (3)	C25—C24—C23	119.7 (4)
C31—N4—P1	117.2 (2)	C25—C24—H24	120.2
C29—N4—P1	125.2 (2)	C23—C24—H24	120.2
C14—C9—C10	116.4 (3)	C24—C25—C26	120.5 (4)
C14—C9—C27	121.6 (3)	C24—C25—H25	119.7
C10—C9—C27	122.0 (2)	C26—C25—H25	119.7
C11—C10—C9	121.9 (3)	C25—C26—C21	120.4 (4)
C11—C10—H10	119.1	C25—C26—H26	119.8
C9—C10—H10	119.1	C21—C26—H26	119.8
C12—C11—C10	117.2 (3)	O6—C27—N2	121.8 (2)
C12—C11—H11	121.4	O6—C27—C9	122.0 (2)
C10—C11—H11	121.4	N2—C27—C9	116.2 (2)
C13—C12—F8	118.3 (3)	N3—C28—C15	112.2 (2)
C13—C12—C11	124.0 (3)	N3—C28—H28A	109.2
F8—C12—C11	117.7 (3)	C15—C28—H28A	109.2
C12—C13—C14	117.0 (3)	N3—C28—H28B	109.2
C12—C13—H13	121.5	C15—C28—H28B	109.2
C14—C13—H13	121.5	H28A—C28—H28B	107.9
F7—C14—C13	117.0 (3)	N4—C29—C21	112.5 (2)
F7—C14—C9	119.4 (3)	N4—C29—H29A	109.1
C13—C14—C9	123.6 (3)	C21—C29—H29A	109.1
C16—C15—C20	118.9 (3)	N4—C29—H29B	109.1
C16—C15—C28	120.8 (3)	C21—C29—H29B	109.1
C20—C15—C28	120.3 (3)	H29A—C29—H29B	107.8
C17—C16—C15	120.8 (3)	N3—C30—H30A	109.5
C17—C16—H16	119.6	N3—C30—H30B	109.5
C15—C16—H16	119.6	H30A—C30—H30B	109.5
C16—C17—C18	120.4 (4)	N3—C30—H30C	109.5
C16—C17—H17	119.8	H30A—C30—H30C	109.5
C18—C17—H17	119.8	H30B—C30—H30C	109.5
C19—C18—C17	119.8 (4)	N4—C31—H31A	109.5
C19—C18—H18	120.1	N4—C31—H31B	109.5
C17—C18—H18	120.1	H31A—C31—H31B	109.5
C18—C19—C20	120.0 (3)	N4—C31—H31C	109.5
C18—C19—H19	120.0	H31A—C31—H31C	109.5
C20—C19—H19	120.0	H31B—C31—H31C	109.5

O5—P1—N2—C27	−152.1 (2)	C28—C15—C16—C17	−179.7 (3)
N3—P1—N2—C27	84.8 (3)	C15—C16—C17—C18	−0.1 (6)
N4—P1—N2—C27	−32.3 (3)	C16—C17—C18—C19	−0.2 (6)
O5—P1—N3—C28	−133.5 (2)	C17—C18—C19—C20	0.3 (6)
N4—P1—N3—C28	102.7 (3)	C16—C15—C20—C19	−0.1 (4)
N2—P1—N3—C28	−15.0 (3)	C28—C15—C20—C19	179.8 (3)
O5—P1—N3—C30	51.3 (3)	C18—C19—C20—C15	−0.2 (5)
N4—P1—N3—C30	−72.4 (3)	C26—C21—C22—C23	−0.2 (5)
N2—P1—N3—C30	169.9 (2)	C29—C21—C22—C23	179.6 (3)
O5—P1—N4—C31	55.7 (3)	C21—C22—C23—C24	1.0 (6)
N3—P1—N4—C31	−178.6 (2)	C22—C23—C24—C25	−0.7 (7)
N2—P1—N4—C31	−61.5 (3)	C23—C24—C25—C26	−0.5 (7)
O5—P1—N4—C29	−146.5 (2)	C24—C25—C26—C21	1.2 (6)
N3—P1—N4—C29	−20.8 (3)	C22—C21—C26—C25	−0.9 (5)
N2—P1—N4—C29	96.3 (2)	C29—C21—C26—C25	179.3 (3)
C14—C9—C10—C11	−0.7 (5)	P1—N2—C27—O6	−18.5 (4)
C27—C9—C10—C11	−179.1 (3)	P1—N2—C27—C9	159.9 (2)
C9—C10—C11—C12	−0.4 (5)	C14—C9—C27—O6	−34.0 (5)
C10—C11—C12—C13	1.2 (6)	C10—C9—C27—O6	144.4 (3)
C10—C11—C12—F8	−177.8 (3)	C14—C9—C27—N2	147.6 (3)
F8—C12—C13—C14	178.3 (3)	C10—C9—C27—N2	−34.1 (4)
C11—C12—C13—C14	−0.7 (5)	C30—N3—C28—C15	−66.2 (4)
C12—C13—C14—F7	−178.3 (3)	P1—N3—C28—C15	118.5 (3)
C12—C13—C14—C9	−0.6 (5)	C16—C15—C28—N3	−58.5 (4)
C10—C9—C14—F7	178.9 (3)	C20—C15—C28—N3	121.6 (3)
C27—C9—C14—F7	−2.7 (5)	C31—N4—C29—C21	−68.0 (3)
C10—C9—C14—C13	1.2 (5)	P1—N4—C29—C21	133.6 (2)
C27—C9—C14—C13	179.7 (3)	C22—C21—C29—N4	148.0 (3)
C20—C15—C16—C17	0.2 (5)	C26—C21—C29—N4	−32.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5ⁱ	0.86	1.96	2.812 (3)	171

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₄F₂N₃O₂P
M_r	443.42
Crystal system, space group	Triclinic, P1
Temperature (K)	300
a, b, c (Å)	10.3619 (6), 10.7721 (10), 11.6433 (8)
α, β, γ (°)	70.523 (7), 72.495 (5), 70.197 (7)
V (Å³)	1126.65 (15)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.44
Crystal size (mm)	0.17 × 0.14 × 0.03

Data collection
Diffractometer	Agilent Xcalibur Gemini R diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.954, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10022, 4209, 2758
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.141, 1.01
No. of reflections	4209
No. of parameters	268
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.27

Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5ⁱ	0.86	1.96	2.812 (3)	171.1

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

Financial support from the Spanish Ministerio de Educacion y Ciencia (MAT2006–01997, MAT2010–15094 and the `Factoría de Cristalización' Consolider Ingenio 2010) and FEDER funding is acknowledged.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England. Google Scholar
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
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Pourayoubi, M., Tarahhomi, A., Rheingold, A. L. & Golen, J. A. (2010). Acta Cryst. E66, o3159. Web of Science CSD CrossRef 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
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Volume 68| Part 2| February 2012| Pages o270-o271

doi:10.1107/S1600536811055115

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N,N′-Di­benzyl-N′′-(2,4-di­fluoro­benzo­yl)-N,N′-di­methyl­phospho­ric tri­amide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N′-Dibenzyl-N′′-(2,4-difluorobenzoyl)-N,N′-dimethylphosphoric triamide