N,N′-Dibenzyl-N′′-(2-chloro-2,2-difluoro­acet­yl)-N,N′-dimethyl­phospho­ric triamide

Raissi Shabari, A.; Pourayoubi, M.; Saneei, A.

doi:10.1107/S1600536811005423

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o663-o664

doi:10.1107/S1600536811005423

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N,N′-Dibenzyl-N′′-(2-chloro-2,2-difluoroacetyl)-N,N′-dimethylphosphoric triamide

Akbar Raissi Shabari,^a ^* Mehrdad Pourayoubi ^b and Anahid Saneei ^b

^aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran
^*Correspondence e-mail: a.raissi_shabari@yahoo.com

(Received 2 February 2011; accepted 14 February 2011; online 19 February 2011)

In the title molecule, C₁₈H₂₁ClF₂N₃O₂P, the P=O and N—H groups are syn to each other. The P atom adopts a slightly distorted tetrahedral environment and the N atoms of the tertiary amine groups are bonded in an essentially planar geometry. In the crystal, pairs of intermolecular N—H⋯O(P) hydrogen bonds form centrosymmetric dimers.

Related literature

For metal complexes with phosphoryl donor ligands, see: Gholivand et al. (2010 ). For a polyoxometalate-based inorganic–organic compound containing a phosphoryl ligand, see: Niu et al. (1996 ). For phosphoric triamide compounds having a C(=O)NHP(=O) skeleton, see: Pourayoubi & Sabbaghi (2009 ) and references cited therein. For bond lengths in related structures, see: Sabbaghi et al. (2010 ). For hydrogen-bond motifs, see: Etter et al. (1990 ); Bernstein et al. (1995 ). For the synthesis of the starting material, CClF₂C(O)NHP(O)Cl₂, see: Iriarte et al. (2008 ).

Experimental

Crystal data

C₁₈H₂₁ClF₂N₃O₂P
M_r = 415.80
Triclinic, $[P \overline 1]$
a = 10.3059 (9) Å
b = 10.5030 (9) Å
c = 10.9473 (9) Å
α = 71.743 (2)°
β = 67.294 (2)°
γ = 63.265 (2)°
V = 962.15 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 120 K
0.28 × 0.22 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.916, T_max = 0.954
9258 measured reflections
4148 independent reflections
3359 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.111
S = 1.00
4148 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond angles (°)

O1—P1—N2	112.34 (9)
O1—P1—N1	117.13 (9)
N2—P1—N1	107.02 (9)
O1—P1—N3	105.06 (9)
N2—P1—N3	110.57 (9)
N1—P1—N3	104.38 (9)
C1—N1—C2	114.36 (17)
C1—N1—P1	126.21 (15)
C2—N1—P1	119.42 (14)
C9—N2—C10	115.45 (17)
C9—N2—P1	121.56 (14)
C10—N2—P1	122.42 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1ⁱ	0.87	1.91	2.772 (3)	174
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005423/lh5205sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005423/lh5205Isup2.hkl

checkCIF report

Comment top

Phosphoryl donor ligands have been used to prepare coordination complexes (Gholivand et al., 2010) and polyoxometalate-based inorganic-organic hybrid compounds (Niu et al., 1996). The structure determination of title compound was performed as a part of a project on the synthesis of new potential phosphoric triamide ligands having a C(═O)NHP(═O) skeleton (Pourayoubi & Sabbaghi, 2009).

In the title compound, C₁₈H₂₁ClF₂N₃O₂P, the phosphoryl group and NH unit are syn to each other and the phosphorus atom has a slightly distorted tetrahedral configuration (Fig. 1). The P atom adopts a slightly distorted tetrahedral environment and the N atoms of the tertiary amine groups are bonded in an essentially planar geometry (see Table 1). The P═O bond length 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 (CClF₂)C(O) unit, the O—C—C—F dihedral angles showing the orientation of flourine atoms relative to carbonyl group are 17.7 (3) and 137.1 (2)° and the O—C—C—Cl dihedral angle is -101.9 (2)°.

The phosphoryl is a better H-acceptor relative to the carbonyl counterpart (Pourayoubi & Sabbaghi, 2009); so, the hydrogen atom of the C(═ O)NHP(═ O) group is involved in an intermolecular –P═O···H—N– hydrogen bond (see Table 2) to form a centrosymmetric dimeric aggregate [graph set: R₂²(8) (Etter et al., 1990; Bernstein et al., 1995)], Fig. 2.

Related literature top

For metal complexes with phosphoryl donor ligands, see: Gholivand et al. (2010). For a polyoxometalate-based inorganic–organic compound containing a phosphoryl ligand, see: Niu et al. (1996). For phosphoric triamide compounds having a C(═O)NHP(═O) skeleton, see: Pourayoubi & Sabbaghi (2009) and references cited therein. For bond lengths in related structures, see: Sabbaghi et al. (2010). For hydrogen-bond motifs, see: Etter et al. (1990); Bernstein et al. (1995). For the synthesis of the starting material, CClF₂C(O)NHP(O)Cl₂, see: Iriarte et al. (2008).

Experimental top

Synthesis of CClF₂C(O)NHP(O)Cl₂: CClF₂C(O)NHP(O)Cl₂ was prepared according to procedure reported by Iriarte et al. (2008) from a reaction between phosphorus pentachloride (16.91 mmol) and CClF₂C(O)NH₂ (16.91 mmol) in dry CCl₄ at 358 K (3 h) and then the treatment of formic acid (16.91 mmol) at ice bath temperature; then removing of solvent in vacuum to yield CClF₂C(O)NHP(O)Cl₂.

Synthesis of title compound: To a solution of CClF₂C(O)NHP(O)Cl₂ (1.04 mmol) in dry CHCl₃, a solution of N-methylbenzylamine (4.16 mmol) in dry CHCl₃ was added dropwise and stirred at 273 K. After 4 h, the solvent was removed at room temperature. The solid was washed with H₂O. The product was obtained after recrystallization from a methanol/n-heptane mixture (4:1) after a slow evaporation at room temperature. IR (KBr, cm^-1): 3066, 2886, 1729 (C═O), 1592, 1481, 1359, 1286, 1218, 1150, 1009, 965, 863, 809, 698. ¹⁹F NMR (470.59 MHz, DMSO-d6, 300 K, CFCl₃): -63.69 p.p.m. (s). ³¹P{¹H} NMR (202.46 MHz, DMSO-d6, 300 K, 85% H₃PO₄): 12.80 p.p.m. (s). ¹H NMR (500.13 MHz, DMSO-d6, 300 K, TMS): 2.48 (s, 3H, CH₃), 2.50 (s, 3H, CH₃), 4.16 (m, 4H, CH₂), 7.25–7.38 (m, 10H, Ar–H), 10.60 p.p.m. (s, 1H, NH). ¹³C NMR (125.76 MHz, DMSO-d6, 300 K, TMS): 33.16 (d, ²J(P,C) = 4.6 Hz, 2 C, CH₃), 51.78 (d, ²J(P,C) = 5.1 Hz, 2 C, CH₂), 118.08 (dt, 1C, CClF₂), 127.17 (s), 127.96 (s), 128.32 (s), 137.68 (d, ³J(P,C) = 3.9 Hz, 2 C, C_ipso), 159.81 p.p.m. (t, ²J(F,C) = 35.0 Hz, 1 C, C═O).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the H-bonded (dashed lines) centrosymmetric dimer (symmetry code: (A) 1-x, 1-y, -z).

N,N'-Dibenzyl-N''-(2-chloro-2,2-difluoroacetyl)- N,N'-dimethylphosphoric triamide top

Crystal data top

C₁₈H₂₁ClF₂N₃O₂P	Z = 2
M_r = 415.80	F(000) = 432
Triclinic, P1	D_x = 1.435 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3059 (9) Å	Cell parameters from 3946 reflections
b = 10.5030 (9) Å	θ = 2.3–29.1°
c = 10.9473 (9) Å	µ = 0.32 mm⁻¹
α = 71.743 (2)°	T = 120 K
β = 67.294 (2)°	Prism, colourless
γ = 63.265 (2)°	0.28 × 0.22 × 0.15 mm
V = 962.15 (14) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4148 independent reflections
Radiation source: fine-focus sealed tube	3359 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −13→13
T_min = 0.916, T_max = 0.954	k = −13→13
9258 measured reflections	l = −13→13

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)] = 0.049	Hydrogen site location: mixed
wR(F²) = 0.111	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0309P)² + 1.6759P] where P = (F_o² + 2F_c²)/3
4148 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₈H₂₁ClF₂N₃O₂P	γ = 63.265 (2)°
M_r = 415.80	V = 962.15 (14) Å³
Triclinic, P1	Z = 2
a = 10.3059 (9) Å	Mo Kα radiation
b = 10.5030 (9) Å	µ = 0.32 mm⁻¹
c = 10.9473 (9) Å	T = 120 K
α = 71.743 (2)°	0.28 × 0.22 × 0.15 mm
β = 67.294 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4148 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	3359 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.954	R_int = 0.025
9258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.00	Δρ_max = 0.39 e Å⁻³
4148 reflections	Δρ_min = −0.37 e Å⁻³
247 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	0.24133 (6)	0.55399 (6)	0.07097 (5)	0.01766 (13)
Cl1	0.40224 (7)	0.93801 (7)	−0.06620 (6)	0.03255 (16)
F1	0.45008 (15)	0.79512 (15)	0.15810 (14)	0.0304 (3)
F2	0.25207 (16)	0.99322 (15)	0.16926 (15)	0.0346 (3)
O1	0.37544 (16)	0.44767 (15)	−0.00684 (15)	0.0207 (3)
O2	0.09472 (17)	0.85802 (17)	0.16326 (17)	0.0290 (4)
N1	0.11179 (19)	0.66717 (19)	−0.00324 (17)	0.0194 (4)
N2	0.1560 (2)	0.47741 (19)	0.21311 (17)	0.0205 (4)
N3	0.3102 (2)	0.66075 (19)	0.09736 (18)	0.0197 (4)
H3N	0.4088	0.6297	0.0731	0.039 (8)*
C1	−0.0432 (3)	0.6755 (3)	0.0358 (2)	0.0300 (5)
H1A	−0.0678	0.6791	−0.0435	0.045*
H1B	−0.1129	0.7630	0.0751	0.045*
H1C	−0.0534	0.5902	0.1021	0.045*
C2	0.1497 (3)	0.7723 (2)	−0.1223 (2)	0.0232 (4)
H2A	0.2436	0.7795	−0.1257	0.028*
H2B	0.0671	0.8685	−0.1125	0.028*
C3	0.1726 (2)	0.7347 (2)	−0.2540 (2)	0.0215 (4)
C4	0.1249 (2)	0.8454 (2)	−0.3561 (2)	0.0241 (5)
H4A	0.0693	0.9420	−0.3396	0.029*
C5	0.1583 (3)	0.8152 (3)	−0.4825 (2)	0.0281 (5)
H5A	0.1265	0.8912	−0.5521	0.034*
C6	0.2378 (3)	0.6744 (3)	−0.5067 (2)	0.0299 (5)
H6A	0.2612	0.6537	−0.5929	0.036*
C7	0.2835 (3)	0.5633 (3)	−0.4041 (2)	0.0293 (5)
H7A	0.3371	0.4666	−0.4204	0.035*
C8	0.2511 (3)	0.5929 (2)	−0.2784 (2)	0.0254 (5)
H8A	0.2825	0.5165	−0.2088	0.030*
C9	0.0398 (3)	0.5614 (2)	0.3182 (2)	0.0254 (5)
H9A	−0.0450	0.5282	0.3573	0.038*
H9B	0.0031	0.6641	0.2790	0.038*
H9C	0.0839	0.5478	0.3885	0.038*
C10	0.2044 (3)	0.3195 (2)	0.2526 (2)	0.0235 (4)
H10A	0.2779	0.2738	0.1736	0.028*
H10B	0.1151	0.2927	0.2808	0.028*
C11	0.2766 (2)	0.2604 (2)	0.3657 (2)	0.0217 (4)
C12	0.4040 (3)	0.2854 (2)	0.3528 (2)	0.0249 (5)
H12A	0.4465	0.3391	0.2720	0.030*
C13	0.4683 (3)	0.2321 (2)	0.4577 (2)	0.0263 (5)
H13A	0.5547	0.2497	0.4485	0.032*
C14	0.4077 (3)	0.1535 (2)	0.5757 (2)	0.0267 (5)
H14A	0.4521	0.1177	0.6473	0.032*
C15	0.2827 (3)	0.1271 (2)	0.5896 (2)	0.0279 (5)
H15A	0.2415	0.0723	0.6702	0.034*
C16	0.2175 (3)	0.1812 (2)	0.4847 (2)	0.0250 (5)
H16A	0.1309	0.1635	0.4948	0.030*
C17	0.2317 (2)	0.7958 (2)	0.1275 (2)	0.0213 (4)
C18	0.3323 (3)	0.8782 (2)	0.1073 (2)	0.0242 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0166 (3)	0.0174 (3)	0.0179 (3)	−0.0063 (2)	−0.0047 (2)	−0.0021 (2)
Cl1	0.0383 (3)	0.0335 (3)	0.0279 (3)	−0.0217 (3)	−0.0053 (2)	−0.0007 (2)
F1	0.0315 (7)	0.0306 (7)	0.0366 (8)	−0.0135 (6)	−0.0154 (6)	−0.0052 (6)
F2	0.0362 (8)	0.0289 (7)	0.0408 (8)	−0.0132 (6)	−0.0024 (6)	−0.0182 (6)
O1	0.0184 (7)	0.0203 (7)	0.0230 (8)	−0.0061 (6)	−0.0055 (6)	−0.0059 (6)
O2	0.0209 (8)	0.0242 (8)	0.0371 (9)	−0.0052 (7)	−0.0030 (7)	−0.0108 (7)
N1	0.0179 (8)	0.0201 (9)	0.0189 (9)	−0.0076 (7)	−0.0057 (7)	−0.0004 (7)
N2	0.0197 (9)	0.0193 (9)	0.0186 (8)	−0.0077 (7)	−0.0038 (7)	0.0002 (7)
N3	0.0167 (8)	0.0188 (9)	0.0237 (9)	−0.0056 (7)	−0.0065 (7)	−0.0044 (7)
C1	0.0195 (11)	0.0406 (14)	0.0272 (12)	−0.0104 (10)	−0.0092 (9)	−0.0002 (10)
C2	0.0294 (11)	0.0194 (10)	0.0213 (11)	−0.0098 (9)	−0.0103 (9)	0.0008 (8)
C3	0.0211 (10)	0.0259 (11)	0.0195 (10)	−0.0124 (9)	−0.0057 (8)	−0.0013 (8)
C4	0.0208 (10)	0.0270 (11)	0.0239 (11)	−0.0105 (9)	−0.0070 (9)	−0.0005 (9)
C5	0.0277 (12)	0.0373 (13)	0.0210 (11)	−0.0146 (10)	−0.0114 (9)	0.0023 (9)
C6	0.0314 (12)	0.0449 (14)	0.0208 (11)	−0.0212 (11)	−0.0062 (9)	−0.0060 (10)
C7	0.0321 (12)	0.0300 (12)	0.0285 (12)	−0.0155 (10)	−0.0046 (10)	−0.0079 (10)
C8	0.0282 (11)	0.0242 (11)	0.0246 (11)	−0.0125 (9)	−0.0084 (9)	0.0001 (9)
C9	0.0250 (11)	0.0295 (12)	0.0173 (10)	−0.0114 (9)	−0.0016 (9)	−0.0023 (9)
C10	0.0275 (11)	0.0203 (10)	0.0243 (11)	−0.0116 (9)	−0.0102 (9)	0.0016 (8)
C11	0.0236 (10)	0.0171 (10)	0.0237 (11)	−0.0063 (8)	−0.0084 (9)	−0.0025 (8)
C12	0.0253 (11)	0.0253 (11)	0.0236 (11)	−0.0119 (9)	−0.0055 (9)	−0.0020 (9)
C13	0.0222 (11)	0.0258 (11)	0.0317 (12)	−0.0078 (9)	−0.0096 (9)	−0.0054 (9)
C14	0.0273 (11)	0.0249 (11)	0.0264 (11)	−0.0042 (9)	−0.0125 (9)	−0.0051 (9)
C15	0.0308 (12)	0.0236 (11)	0.0241 (11)	−0.0102 (10)	−0.0080 (9)	0.0026 (9)
C16	0.0242 (11)	0.0245 (11)	0.0268 (11)	−0.0116 (9)	−0.0092 (9)	0.0013 (9)
C17	0.0235 (11)	0.0205 (10)	0.0192 (10)	−0.0088 (9)	−0.0054 (8)	−0.0025 (8)
C18	0.0249 (11)	0.0205 (10)	0.0261 (11)	−0.0072 (9)	−0.0055 (9)	−0.0068 (9)

Geometric parameters (Å, º) top

P1—O1	1.4769 (15)	C5—H5A	0.9500
P1—N2	1.6241 (18)	C6—C7	1.391 (3)
P1—N1	1.6308 (18)	C6—H6A	0.9500
P1—N3	1.7093 (18)	C7—C8	1.387 (3)
Cl1—C18	1.768 (2)	C7—H7A	0.9500
F1—C18	1.345 (3)	C8—H8A	0.9500
F2—C18	1.336 (2)	C9—H9A	0.9800
O2—C17	1.215 (3)	C9—H9B	0.9800
N1—C1	1.453 (3)	C9—H9C	0.9800
N1—C2	1.471 (3)	C10—C11	1.512 (3)
N2—C9	1.469 (3)	C10—H10A	0.9900
N2—C10	1.469 (3)	C10—H10B	0.9900
N3—C17	1.353 (3)	C11—C16	1.387 (3)
N3—H3N	0.8700	C11—C12	1.399 (3)
C1—H1A	0.9800	C12—C13	1.387 (3)
C1—H1B	0.9800	C12—H12A	0.9500
C1—H1C	0.9800	C13—C14	1.383 (3)
C2—C3	1.517 (3)	C13—H13A	0.9500
C2—H2A	0.9900	C14—C15	1.379 (3)
C2—H2B	0.9900	C14—H14A	0.9500
C3—C4	1.393 (3)	C15—C16	1.391 (3)
C3—C8	1.394 (3)	C15—H15A	0.9500
C4—C5	1.394 (3)	C16—H16A	0.9500
C4—H4A	0.9500	C17—C18	1.543 (3)
C5—C6	1.384 (4)

O1—P1—N2	112.34 (9)	C7—C8—C3	120.0 (2)
O1—P1—N1	117.13 (9)	C7—C8—H8A	120.0
N2—P1—N1	107.02 (9)	C3—C8—H8A	120.0
O1—P1—N3	105.06 (9)	N2—C9—H9A	109.5
N2—P1—N3	110.57 (9)	N2—C9—H9B	109.5
N1—P1—N3	104.38 (9)	H9A—C9—H9B	109.5
C1—N1—C2	114.36 (17)	N2—C9—H9C	109.5
C1—N1—P1	126.21 (15)	H9A—C9—H9C	109.5
C2—N1—P1	119.42 (14)	H9B—C9—H9C	109.5
C9—N2—C10	115.45 (17)	N2—C10—C11	113.28 (18)
C9—N2—P1	121.56 (14)	N2—C10—H10A	108.9
C10—N2—P1	122.42 (15)	C11—C10—H10A	108.9
C17—N3—P1	127.29 (15)	N2—C10—H10B	108.9
C17—N3—H3N	117.5	C11—C10—H10B	108.9
P1—N3—H3N	114.0	H10A—C10—H10B	107.7
N1—C1—H1A	109.5	C16—C11—C12	118.6 (2)
N1—C1—H1B	109.5	C16—C11—C10	120.9 (2)
H1A—C1—H1B	109.5	C12—C11—C10	120.59 (19)
N1—C1—H1C	109.5	C13—C12—C11	120.2 (2)
H1A—C1—H1C	109.5	C13—C12—H12A	119.9
H1B—C1—H1C	109.5	C11—C12—H12A	119.9
N1—C2—C3	114.05 (17)	C14—C13—C12	120.4 (2)
N1—C2—H2A	108.7	C14—C13—H13A	119.8
C3—C2—H2A	108.7	C12—C13—H13A	119.8
N1—C2—H2B	108.7	C15—C14—C13	120.1 (2)
C3—C2—H2B	108.7	C15—C14—H14A	120.0
H2A—C2—H2B	107.6	C13—C14—H14A	120.0
C4—C3—C8	119.4 (2)	C14—C15—C16	119.6 (2)
C4—C3—C2	119.3 (2)	C14—C15—H15A	120.2
C8—C3—C2	121.15 (19)	C16—C15—H15A	120.2
C3—C4—C5	120.3 (2)	C11—C16—C15	121.2 (2)
C3—C4—H4A	119.8	C11—C16—H16A	119.4
C5—C4—H4A	119.8	C15—C16—H16A	119.4
C6—C5—C4	120.1 (2)	O2—C17—N3	127.4 (2)
C6—C5—H5A	120.0	O2—C17—C18	118.39 (19)
C4—C5—H5A	120.0	N3—C17—C18	114.16 (18)
C5—C6—C7	119.7 (2)	F2—C18—F1	107.18 (18)
C5—C6—H6A	120.1	F2—C18—C17	110.49 (18)
C7—C6—H6A	120.1	F1—C18—C17	111.98 (17)
C8—C7—C6	120.5 (2)	F2—C18—Cl1	108.70 (15)
C8—C7—H7A	119.8	F1—C18—Cl1	109.06 (15)
C6—C7—H7A	119.8	C17—C18—Cl1	109.35 (15)

O1—P1—N1—C1	115.12 (19)	C6—C7—C8—C3	−0.1 (3)
N2—P1—N1—C1	−12.0 (2)	C4—C3—C8—C7	1.2 (3)
N3—P1—N1—C1	−129.24 (19)	C2—C3—C8—C7	−173.7 (2)
O1—P1—N1—C2	−64.27 (18)	C9—N2—C10—C11	−61.8 (2)
N2—P1—N1—C2	168.61 (15)	P1—N2—C10—C11	109.64 (19)
N3—P1—N1—C2	51.38 (17)	N2—C10—C11—C16	122.1 (2)
O1—P1—N2—C9	167.42 (16)	N2—C10—C11—C12	−57.4 (3)
N1—P1—N2—C9	−62.69 (18)	C16—C11—C12—C13	−0.2 (3)
N3—P1—N2—C9	50.40 (19)	C10—C11—C12—C13	179.2 (2)
O1—P1—N2—C10	−3.55 (19)	C11—C12—C13—C14	0.2 (3)
N1—P1—N2—C10	126.34 (17)	C12—C13—C14—C15	0.3 (3)
N3—P1—N2—C10	−120.57 (16)	C13—C14—C15—C16	−0.6 (3)
O1—P1—N3—C17	158.89 (18)	C12—C11—C16—C15	−0.1 (3)
N2—P1—N3—C17	−79.68 (19)	C10—C11—C16—C15	−179.6 (2)
N1—P1—N3—C17	35.1 (2)	C14—C15—C16—C11	0.6 (4)
C1—N1—C2—C3	−75.1 (2)	P1—N3—C17—O2	13.3 (3)
P1—N1—C2—C3	104.32 (19)	P1—N3—C17—C18	−164.20 (15)
N1—C2—C3—C4	143.87 (19)	O2—C17—C18—F2	17.7 (3)
N1—C2—C3—C8	−41.2 (3)	N3—C17—C18—F2	−164.59 (18)
C8—C3—C4—C5	−1.5 (3)	O2—C17—C18—F1	137.1 (2)
C2—C3—C4—C5	173.5 (2)	N3—C17—C18—F1	−45.2 (2)
C3—C4—C5—C6	0.7 (3)	O2—C17—C18—Cl1	−101.9 (2)
C4—C5—C6—C7	0.4 (3)	N3—C17—C18—Cl1	75.8 (2)
C5—C6—C7—C8	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.87	1.91	2.772 (3)	174

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁ClF₂N₃O₂P
M_r	415.80
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	10.3059 (9), 10.5030 (9), 10.9473 (9)
α, β, γ (°)	71.743 (2), 67.294 (2), 63.265 (2)
V (Å³)	962.15 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.28 × 0.22 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.916, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	9258, 4148, 3359
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.111, 1.00
No. of reflections	4148
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.37

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Selected bond angles (º) top

O1—P1—N2	112.34 (9)	C1—N1—C2	114.36 (17)
O1—P1—N1	117.13 (9)	C1—N1—P1	126.21 (15)
N2—P1—N1	107.02 (9)	C2—N1—P1	119.42 (14)
O1—P1—N3	105.06 (9)	C9—N2—C10	115.45 (17)
N2—P1—N3	110.57 (9)	C9—N2—P1	121.56 (14)
N1—P1—N3	104.38 (9)	C10—N2—P1	122.42 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.87	1.91	2.772 (3)	174

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

Support of this investigation by Islamic Azad University–North Tehran Branch is gratefully acknowledged.

References

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
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Volume 67| Part 3| March 2011| Pages o663-o664

doi:10.1107/S1600536811005423

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

N,N′-Di­benzyl-N′′-(2-chloro-2,2-di­fluoro­acet­yl)-N,N′-di­methyl­phospho­ric tri­amide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

N,N′-Dibenzyl-N′′-(2-chloro-2,2-difluoroacetyl)-N,N′-dimethylphosphoric triamide