N,N′-Dimethyl-N,N′-diphenyl-3-oxa­penta­nediamide

Shaohong Yin; Yu Cui; Guangpu Wu; Qi You; Guoxin Sun

doi:10.1107/S1600536809022806

. 2009 Jun 20;65(Pt 7):o1654. doi: 10.1107/S1600536809022806

N,N′-Dimethyl-N,N′-diphenyl-3-oxapentanediamide

Shaohong Yin ^a, Yu Cui ^a, Guangpu Wu ^a, Qi You ^a, Guoxin Sun ^a,^*

PMCID: PMC2969191 PMID: 21582917

Abstract

In the title compound, C₁₈H₂₀N₂O₃, the two phenyl rings, adopt opposite orientations in the backbone and are oriented at a dihedral angle of 36.66 (3)°. In the crystal, intermolecular C—H⋯O interactions link the molecules into a three-dimensional network.

Related literature

For a related structure, see: Zhang et al. (2001 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₈H₂₀N₂O₃
M _r = 312.36
Monoclinic,
a = 10.7607 (11) Å
b = 10.7552 (12) Å
c = 14.7054 (14) Å
β = 102.897 (1)°
V = 1659.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.49 × 0.48 × 0.42 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.959, T _max = 0.965
8254 measured reflections
2897 independent reflections
1644 reflections with I > 2σ(I)
R _int = 0.082

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.159
S = 1.04
2897 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022806/hk2708sup1.cif

e-65-o1654-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022806/hk2708Isup2.hkl

e-65-o1654-Isup2.hkl^{(142.2KB, 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
C7—H7⋯O3ⁱ	0.93	2.53	3.436 (3)	165
C9—H9⋯O1ⁱⁱ	0.93	2.47	3.337 (3)	155
C12—H12B⋯O1ⁱⁱⁱ	0.96	2.48	3.346 (3)	151
C17—H17⋯O2^iv	0.93	2.52	3.432 (3)	167

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors thank the National Science Foundation of China (grant No. 203010008), the Science Foundation of Shandong Province (grant No. Q2003B01) and Key Subject Research Foundation of Shandong Province for support of this work.

supplementary crystallographic information

Comment

3-Oxapentanediamide derivatives show a highly selective complexation of lanthanide. We are interested in their performance to extract lanthanide ions. To obtain more information on the structural character and the reactivity of ligand with different lanthanide ions, we report herein the crystal structure of the title compound.

In the structure of the title compound (Fig 1), the bond lengths and angles are within normal ranges (Allen et al., 1987) and may be compared with the corresponding values in N,N'-diethyl-N,N'-diphenyl-3-oxapentanediamide (Zhang et al., 2001). The framework of the molecule is composed of a zigzag chain (C2—C1—O3—C10—C11) with two methylphenyl amide terminal groups. An interesting aspect of the molecular conformation concerns the two phenyl rings, which adopt opposite orientations in the backbone, and they are oriented at a dihedral angle of 36.66 (3)°. The moieties (O1/O3/N1/C1-C3) and (O2/N2/C10-C13) are planar [with maximum deviations of -0.036 (3) and 0.021 (3) Å for atoms C3 and C10, respectively] and the dihedral angle between them is 24.67 (3)°, which are oriented with respect to the adjacent rings A (C4-C9) and B (C13-C18) at dihedral angles of 72.97 (4) and 70.17 (3) °, respectively. Intramolecular C-H···O interactions (Table 1) result in the formation of a six-membered ring C (O1/O3/C1/C2/C10/H10B) having twisted conformation, and two five-membered rings D (O1/N1/C2/C3/H3A) and E (O2/N2/C11/C12/H12C) having envelope conformations with atoms H3A and H12C displaced by -0.415 (4) and -0.257 (5) Å. In the crystal structure, intermolecular C-H···O interactions (Table 1) link the molecules into a three-dimensional network.

Experimental

For the preparation of the title compound, a solution of diglycolic chloride (10 mmol) in anhydrous benzene (3 ml) was added dropwise to a mixture of N-methylphenylamine (25 mmol), anhydrous pyridine (2 ml) in anhydrous benzene (12.5 ml) in the ice-water bath. The mixture was stirred for 3 h, and then for another 3 h at room temperature. The crude product was recrystallized from toluene as the white solid (yield; 65%, m.p. 375 K). Crystals suitable for X-ray analysis were obtained from toluene by slow evaporation over a period of several days. C₁₈H₂₀N₂O₃: C 69.21, H 6.45, N 8.97%; found: C 69.09, H 6.32, N 8.78%. IR (KBr): v = 3056, 2973, 1666, 1593, 1497, 1120, 782, 704 cm ^-1.