N,N′-Dibenzyl-2,2′-[(1,3,4-oxadiazole-2,5-di­yl)bis­(o-phenyl­eneoxy)]diacet­amide

Wang, W.; Huang, Y.; Tang, N.

doi:10.1107/S1600536808033904

organic compounds

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doi:10.1107/S1600536808033904

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N,N′-Dibenzyl-2,2′-[(1,3,4-oxadiazole-2,5-diyl)bis(o-phenyleneoxy)]diacetamide

Wei Wang,^a Yong Huang ^a and Ning Tang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu, People's Republic of China
^*Correspondence e-mail: tangn@lzu.edu.cn

(Received 26 September 2008; accepted 17 October 2008; online 31 October 2008)

The compound, C₃₂H₂₈N₄O₅, which was synthesized by the reaction of 2,5-bis(2-hydroxylphenyl)-1,3,4-oxadiazole with N-benzyl-2-chloroacetamide, lies on a twofold rotation axis which passes through the mid-point of the N—N bond and the O atom of the oxadiazole unit. The phenylene and oxadiazole rings are almost coplanar [dihedral angle 1.67 (5)°]. The structure is stabilized by intramolecular N—H⋯O and N—H⋯N hydrogen bonds.

Related literature

For the biological and physical properties of 1,3,4-oxadiazole derivatives, see Gómez-Saiz et al. (2002 ); Wen et al. (2003 ); Kuo et al. (2006 ). For literature on metal complexes, see Dong et al. (2003 ); Zhou et al. (1996 ).

Experimental

Crystal data

C₃₂H₂₈N₄O₅
M_r = 548.58
Monoclinic, C 2/c
a = 17.0619 (15) Å
b = 15.2601 (15) Å
c = 10.6555 (9) Å
β = 90.611 (5)°
V = 2774.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.53 × 0.40 × 0.30 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: none
7913 measured reflections
2880 independent reflections
2335 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.158
S = 1.17
2880 reflections
187 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.86	2.15	2.5523 (16)	109
N2—H2A⋯N1	0.86	2.49	3.3524 (17)	177

Data collection: APEX2 (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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033904/ng2497sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033904/ng2497Isup2.hkl

checkCIF report

Comment top

Heterocyclic 1,3,4-oxadiazole and its derivatives have been studied for a long time because many of these derivatives show biological activity (Patricia et al., 2002) and electron-transporting capability (Wen et al., 2003), in particular as active compounds in organic light emitting diodes (OLEDs) (Kuo et al., 2006). At the same time, these five-membered oxadiazole ring can bind metal ions by N and O donors to expand various novel polymeric frameworks, some with open channels and interesting luminescence properties (Dong et al., 2003). We herein report the synthesis and crystal structure of a new amide-based 1,3,4-oxadiazole bridging ligand, namely the title compound, (I).

As seen from Fig. 1, the molecule of (I) possesses crystallographically imposed C₂ symmetry, with the two fold axis bisecting the central 1,3,4-oxadiazole ring. The central two phenyl rings and oxadiazole ring are almost coplanar. The amide groups of molecule appear to form intramolecular hydrogen bonds with both the phenoxy O atom and the oxadiazole N atom (Table 1). In addition, the centroid-to-centroid distance (4.344 Å) of the two terminal benzene rings is so much longer that it is difficult to regard this as representing a significantly π-π stacking interaction.

Related literature top

For the biological and physical properties of 1,3,4-oxadiazole derivatives, see Patricia et al. (2002); Wen et al. (20035); Kuo et al. (2006). For literature on metal complexes, see Dong et al. (2003); Zhou et al. (1996).

Experimental top

To 2,5-bis[2'-hydroxyl-phenyl]-1,3,4-oxadiazole (Zhou et al., 1996) (1.78 g, 7 mmol) in DMF (80 ml) was added sodium hydroxide (0.56 g, 14 mmol). The mixture was heated to 353 K and stirred for about 1 h. A solution of N-benzyl-2-chloroacetamide (2.94 g, 16 mmol) and potassium iodide (0.83 g, 5 mmol) in DMF (20 ml) was then added dropwise at a constant rate over 1 h. The reaction mixture was stirred at ca 353 K for an additional 48 h. The solvent was removed under vacuum, and then the residue was treated with water (100 ml). The precipitate was collected by filtration and washed with water (100 ml), then twice recrystallized from methanol to give colourless block crystals. ¹H NMR (400M Hz; CDCl₃, δ, p.p.m): 9.19 (t, 2H, N—H, J = 6 Hz), 8.04 (d, 2H, Ar—H, J = 8 Hz), 7.58 (t, 2H, Ar—H, J = 8 Hz), 7.24–7.15 (m, 12H, Ar—H), 7.06 (d, 2H, Ar—H, J = 8 Hz), 4.72 (s, 4H, O—CH₂), 4.32 (d, 4H, Ar—CH₂—N, J= 6 Hz); Yield 2.30 g (60%); m.p. 462–464 K; elemental analysis, calculated for C₃₂H₂₈N₄O₅, C 70.06, H 5.14, N 10.21%; found: C 70.18, H 5.02, N 10.22%. Colourless single crystals suitable for an X-ray diffraction study were obtained by slow evaporation of the methanol solvent at room temperature over a period of 5 d.

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing 20% probability displacement ellipsoids and the atom-labelling scheme. The intramolecular hydrogen bonds are shown as dashed lines.

N,N'-Dibenzyl-2,2'-[(1,3,4-oxadiazole-2,5-diyl)bis(o-phenyleneoxy)]diacetamide top

Crystal data top

C₃₂H₂₈N₄O₅	F(000) = 1152
M_r = 548.58	D_x = 1.313 Mg m⁻³
Monoclinic, C2/c	Melting point: 462 K
Hall symbol: -C2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.0619 (15) Å	Cell parameters from 3319 reflections
b = 15.2601 (15) Å	θ = 2.4–27.5°
c = 10.6555 (9) Å	µ = 0.09 mm⁻¹
β = 90.611 (5)°	T = 293 K
V = 2774.2 (4) Å³	Block, colourless
Z = 4	0.53 × 0.40 × 0.30 mm

Data collection top

Bruker APEXII diffractometer	2335 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 26.5°, θ_min = 1.8°
ϕ and ω scans	h = −21→20
7913 measured reflections	k = −12→19
2880 independent reflections	l = −13→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max = 0.001
2880 reflections	Δρ_max = 0.18 e Å⁻³
187 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0054 (10)

Crystal data top

C₃₂H₂₈N₄O₅	V = 2774.2 (4) Å³
M_r = 548.58	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.0619 (15) Å	µ = 0.09 mm⁻¹
b = 15.2601 (15) Å	T = 293 K
c = 10.6555 (9) Å	0.53 × 0.40 × 0.30 mm
β = 90.611 (5)°

Data collection top

Bruker APEXII diffractometer	2335 reflections with I > 2σ(I)
7913 measured reflections	R_int = 0.022
2880 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.17	Δρ_max = 0.18 e Å⁻³
2880 reflections	Δρ_min = −0.13 e Å⁻³
187 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
O1	0.5000	1.06829 (8)	0.7500	0.0488 (3)
O2	0.37163 (7)	0.91715 (7)	0.50427 (11)	0.0724 (4)
O3	0.32801 (7)	0.70855 (8)	0.38437 (12)	0.0822 (4)
N1	0.47305 (7)	0.93150 (7)	0.69949 (10)	0.0494 (3)
N2	0.41511 (7)	0.75799 (8)	0.52944 (11)	0.0586 (3)
H2A	0.4317	0.8025	0.5714	0.070*
C1	0.45891 (7)	1.01308 (8)	0.67330 (11)	0.0443 (3)
C2	0.40733 (7)	1.05489 (9)	0.58052 (11)	0.0466 (3)
C3	0.40137 (9)	1.14557 (10)	0.57514 (13)	0.0580 (4)
H3A	0.4307	1.1796	0.6308	0.070*
C4	0.35278 (9)	1.18603 (10)	0.48861 (15)	0.0677 (4)
H4A	0.3493	1.2468	0.4865	0.081*
C5	0.30953 (9)	1.13641 (11)	0.40562 (15)	0.0650 (4)
H5A	0.2772	1.1639	0.3469	0.078*
C6	0.31367 (8)	1.04601 (10)	0.40866 (14)	0.0582 (4)
H6A	0.2839	1.0127	0.3528	0.070*
C7	0.36253 (7)	1.00528 (9)	0.49553 (11)	0.0496 (3)
C8	0.32734 (8)	0.86010 (9)	0.42649 (13)	0.0560 (4)
H8A	0.3328	0.8770	0.3392	0.067*
H8B	0.2723	0.8633	0.4480	0.067*
C9	0.35711 (8)	0.76851 (9)	0.44569 (13)	0.0558 (4)
C10	0.45065 (9)	0.67305 (10)	0.55103 (16)	0.0654 (4)
H10A	0.5040	0.6820	0.5809	0.078*
H10B	0.4534	0.6424	0.4714	0.078*
C11	0.40855 (7)	0.61462 (8)	0.64410 (12)	0.0508 (3)
C12	0.41917 (10)	0.52501 (10)	0.63923 (16)	0.0682 (4)
H12A	0.4500	0.5013	0.5762	0.082*
C13	0.38524 (10)	0.46989 (11)	0.72545 (16)	0.0738 (5)
H13A	0.3937	0.4098	0.7209	0.089*
C14	0.33913 (10)	0.50362 (12)	0.81753 (14)	0.0709 (5)
H14A	0.3168	0.4668	0.8768	0.085*
C15	0.32603 (11)	0.59234 (12)	0.82183 (15)	0.0785 (5)
H15A	0.2937	0.6156	0.8832	0.094*
C16	0.36072 (10)	0.64747 (10)	0.73521 (14)	0.0666 (4)
H16A	0.3514	0.7075	0.7390	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0557 (7)	0.0377 (7)	0.0528 (7)	0.000	−0.0038 (6)	0.000
O2	0.0861 (8)	0.0440 (6)	0.0862 (8)	0.0010 (5)	−0.0371 (6)	−0.0052 (5)
O3	0.0976 (9)	0.0571 (8)	0.0913 (8)	−0.0035 (6)	−0.0217 (7)	−0.0175 (6)
N1	0.0536 (6)	0.0409 (6)	0.0537 (6)	−0.0004 (5)	−0.0055 (5)	−0.0002 (4)
N2	0.0599 (7)	0.0475 (7)	0.0682 (8)	−0.0027 (5)	−0.0049 (6)	0.0025 (5)
C1	0.0460 (6)	0.0409 (7)	0.0461 (7)	−0.0030 (5)	0.0036 (5)	−0.0002 (5)
C2	0.0466 (7)	0.0435 (7)	0.0496 (7)	−0.0019 (5)	0.0049 (5)	0.0055 (5)
C3	0.0656 (8)	0.0450 (8)	0.0632 (9)	−0.0054 (6)	−0.0017 (7)	0.0075 (6)
C4	0.0776 (10)	0.0459 (8)	0.0794 (11)	0.0010 (7)	−0.0042 (8)	0.0185 (7)
C5	0.0630 (9)	0.0619 (10)	0.0699 (9)	0.0028 (7)	−0.0057 (7)	0.0227 (7)
C6	0.0556 (8)	0.0609 (9)	0.0581 (8)	−0.0002 (6)	−0.0055 (6)	0.0075 (6)
C7	0.0506 (7)	0.0446 (7)	0.0536 (7)	−0.0002 (6)	0.0006 (6)	0.0047 (5)
C8	0.0567 (7)	0.0526 (9)	0.0584 (8)	−0.0057 (6)	−0.0091 (6)	−0.0043 (6)
C9	0.0578 (8)	0.0503 (8)	0.0593 (8)	−0.0043 (6)	0.0004 (6)	−0.0044 (6)
C10	0.0572 (8)	0.0597 (10)	0.0794 (10)	0.0068 (7)	0.0053 (7)	0.0083 (7)
C11	0.0485 (7)	0.0522 (8)	0.0516 (7)	0.0032 (6)	−0.0073 (5)	−0.0003 (5)
C12	0.0724 (10)	0.0589 (9)	0.0734 (10)	0.0188 (7)	0.0086 (8)	0.0065 (7)
C13	0.0816 (11)	0.0548 (9)	0.0850 (12)	0.0083 (8)	−0.0040 (9)	0.0156 (8)
C14	0.0796 (10)	0.0749 (11)	0.0581 (9)	−0.0146 (9)	−0.0069 (8)	0.0125 (7)
C15	0.0893 (12)	0.0861 (13)	0.0603 (10)	−0.0136 (10)	0.0152 (9)	−0.0130 (8)
C16	0.0819 (10)	0.0534 (8)	0.0644 (9)	−0.0039 (7)	0.0056 (7)	−0.0143 (7)

Geometric parameters (Å, º) top

O1—C1	1.3627 (14)	C6—C7	1.3863 (18)
O1—C1ⁱ	1.3627 (14)	C6—H6A	0.9300
O2—C7	1.3570 (16)	C8—C9	1.500 (2)
O2—C8	1.4151 (16)	C8—H8A	0.9700
O3—C9	1.2262 (17)	C8—H8B	0.9700
N1—C1	1.2979 (16)	C10—C11	1.5197 (19)
N1—N1ⁱ	1.408 (2)	C10—H10A	0.9700
N2—C9	1.3352 (19)	C10—H10B	0.9700
N2—C10	1.4484 (19)	C11—C16	1.3699 (19)
N2—H2A	0.8600	C11—C12	1.3805 (19)
C1—C2	1.4630 (16)	C12—C13	1.378 (2)
C2—C3	1.389 (2)	C12—H12A	0.9300
C2—C7	1.4009 (17)	C13—C14	1.365 (2)
C3—C4	1.379 (2)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.373 (2)
C4—C5	1.373 (2)	C14—H14A	0.9300
C4—H4A	0.9300	C15—C16	1.386 (2)
C5—C6	1.382 (2)	C15—H15A	0.9300
C5—H5A	0.9300	C16—H16A	0.9300

C1—O1—C1ⁱ	103.62 (13)	O2—C8—H8B	110.0
C7—O2—C8	120.64 (11)	C9—C8—H8B	110.0
C1—N1—N1ⁱ	106.43 (7)	H8A—C8—H8B	108.4
C9—N2—C10	121.32 (13)	O3—C9—N2	124.01 (14)
C9—N2—H2A	119.3	O3—C9—C8	119.20 (14)
C10—N2—H2A	119.3	N2—C9—C8	116.78 (12)
N1—C1—O1	111.76 (11)	N2—C10—C11	115.39 (11)
N1—C1—C2	132.28 (12)	N2—C10—H10A	108.4
O1—C1—C2	115.95 (11)	C11—C10—H10A	108.4
C3—C2—C7	118.20 (12)	N2—C10—H10B	108.4
C3—C2—C1	120.38 (12)	C11—C10—H10B	108.4
C7—C2—C1	121.42 (12)	H10A—C10—H10B	107.5
C4—C3—C2	121.12 (14)	C16—C11—C12	117.94 (13)
C4—C3—H3A	119.4	C16—C11—C10	122.48 (13)
C2—C3—H3A	119.4	C12—C11—C10	119.57 (12)
C5—C4—C3	119.91 (15)	C13—C12—C11	121.56 (14)
C5—C4—H4A	120.0	C13—C12—H12A	119.2
C3—C4—H4A	120.0	C11—C12—H12A	119.2
C4—C5—C6	120.56 (14)	C14—C13—C12	119.91 (16)
C4—C5—H5A	119.7	C14—C13—H13A	120.0
C6—C5—H5A	119.7	C12—C13—H13A	120.0
C5—C6—C7	119.57 (14)	C13—C14—C15	119.41 (14)
C5—C6—H6A	120.2	C13—C14—H14A	120.3
C7—C6—H6A	120.2	C15—C14—H14A	120.3
O2—C7—C6	123.90 (12)	C14—C15—C16	120.36 (15)
O2—C7—C2	115.47 (11)	C14—C15—H15A	119.8
C6—C7—C2	120.63 (13)	C16—C15—H15A	119.8
O2—C8—C9	108.39 (12)	C11—C16—C15	120.77 (15)
O2—C8—H8A	110.0	C11—C16—H16A	119.6
C9—C8—H8A	110.0	C15—C16—H16A	119.6

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	2.15	2.5523 (16)	109
N2—H2A···N1	0.86	2.49	3.3524 (17)	177

Experimental details

Crystal data
Chemical formula	C₃₂H₂₈N₄O₅
M_r	548.58
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	17.0619 (15), 15.2601 (15), 10.6555 (9)
β (°)	90.611 (5)
V (Å³)	2774.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.53 × 0.40 × 0.30

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7913, 2880, 2335
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.158, 1.17
No. of reflections	2880
No. of parameters	187
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.13

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	2.15	2.5523 (16)	109
N2—H2A···N1	0.86	2.49	3.3524 (17)	177

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20571035) and the Interdisciplinary Innovation Research Fund for Young Scholars, Lanzhou University (grant No. LZU200506).

References

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

N,N′-Di­benzyl-2,2′-[(1,3,4-oxa­diazole-2,5-di­yl)bis­­(o-phenyl­ene­oxy)]diacet­amide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N′-Dibenzyl-2,2′-[(1,3,4-oxadiazole-2,5-diyl)bis(o-phenyleneoxy)]diacetamide