N,N′-Dicyclo­hexyl-N,N′-dimethyl-N′′-(4-nitro­benzo­yl)phospho­ric triamide

Fahimeh Sabbaghi; Mahnaz Rostami Chaijan; Mehrdad Pourayoubi

doi:10.1107/S1600536810023524

. 2010 Jun 23;66(Pt 7):o1754. doi: 10.1107/S1600536810023524

N,N′-Dicyclohexyl-N,N′-dimethyl-N′′-(4-nitrobenzoyl)phosphoric triamide

Fahimeh Sabbaghi ^a,^*, Mahnaz Rostami Chaijan ^b, Mehrdad Pourayoubi ^b

PMCID: PMC3006933 PMID: 21587970

Abstract

The P atom in the title compound, C₂₁H₃₃N₄O₄P, is in a slightly distorted tetrahedral coordination environment and the phosphoryl and carbonyl groups are anti to each other. The environment of each N atom is essentially planar (average angles of 119.9 and 118.4°). In the crystal structure, the H atom of the C(=O)NHP(=O) group is involved in an intermolecular –P=O⋯H–N– hydrogen bond, forming centrosymmetric dimers.

Related literature

For applications of compounds containing the –C(=O)NHP(=O)– skeleton, see: Gholivand et al. (2010 ▶). For related structures, see: Pourayoubi & Sabbaghi (2009 ▶); Sabbaghi et al. (2010 ▶).

Experimental

Crystal data

C₂₁H₃₃N₄O₄P
M _r = 436.48
Triclinic,
a = 8.6118 (16) Å
b = 10.838 (2) Å
c = 12.711 (2) Å
α = 93.089 (4)°
β = 106.792 (4)°
γ = 95.105 (3)°
V = 1127.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 120 K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T _min = 0.959, T _max = 0.969
12417 measured reflections
5955 independent reflections
4603 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.103
S = 1.00
5955 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.43 e Å⁻³

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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023524/lh5061sup1.cif

e-66-o1754-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023524/lh5061Isup2.hkl

e-66-o1754-Isup2.hkl^{(291.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	1.91	2.7622 (18)	167

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Symmetry code: (i) Inline graphic .

Acknowledgments

Support of this investigation by Islamic Azad University-Zanjan Branch is gratefully acknowledged.

supplementary crystallographic information

Comment

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). In the previous work, the structures of two compounds with a P(O)[NHC(O)C₆H₄(4-NO₂)] moiety have been investigated: P(O)[NHC(O)C₆H₄(4-NO₂)][N(CH(CH₃)₂)(CH₂C₆H₅)]₂ (Pourayoubi & Sabbaghi, 2009) and P(O)[NHC(O)C₆H₄(4-NO₂)][NHC₆H₁₁]₂ (Sabbaghi et al., 2010). Here, we report the synthesis and crystal structure of a third compound, P(O)[NHC(O)C₆H₄(4-NO₂)][N(CH₃)(C₆H₁₁)]₂. The phosphoryl and carbonyl groups are anti to each other and the phosphorus atom has a slightly distorted tetrahedral configuration (Fig 1). The bond angles around the P atom are in the range of 104.81 (7)°-117.28 (8)°. The P1–N3 and P1–N4 bond lengths (1.6315 (15) Å and 1.6446 (15) Å) are shorter than the P1–N1 bond (1.6859 (14) Å). The environment of the nitrogen atoms is essentially planar; the angles C8–N3–P1, C8–N3–C9 and P1–N3–C9 are 124.25 (12)°, 117.46 (14)° and 118.02 (11)°, respectively (with average = 119.9°). A similar result was obtained for the bond angles around N4 atom (average = 118.4°). Furthermore, the angle C1–N1–P1 is 125.20 (12)°. The P═O bond length of 1.4834 (13) Å is standard for phosphoramidate compounds. The hydrogen atom of the C(═O)NHP(═O) group is involved in an intermolecular –P═O···H—N– hydrogen bond (see Table 1) to form a centrosymmetric dimeric aggregate. A view of crystal packing along the a axis is shown in Fig. 2.

Experimental

4-NO₂—C₆H₄C(O)NHP(O)Cl₂ was prepared according to the procedure of literature (Sabbaghi et al., 2010). To a solution of (0.566 g, 2 mmol) 4-NO₂C₆H₄C(O)NHP(O)Cl₂ in CH₃CN (20 ml), a solution of N-methylcyclohexylamine (0.906 g, 8 mmol) in CH₃CN (5 ml) was added dropwise at 273K. After 4 h the solvent was removed in vacuum. Single crystals were obtained from a solution of title compound in CH₃CN and n-C₆H₁₄ (4:1) after slow evaporation at room temperature. IR (KBr, cm^-1): 3063, 2930, 2855, 1685, 1523, 1453, 1340, 1267, 1183, 1106, 1004, 848, 712.