N,N′-Di-8-quinolyl-2,2′-(o-phenyl­ene­di­oxy)diacetamide

Wang, J.-L.

doi:10.1107/S1600536809041312

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2844

https://doi.org/10.1107/S1600536809041312

Open

access

N,N′-Di-8-quinolyl-2,2′-(o-phenylenedioxy)diacetamide

Jing-Lin Wang ^a ^*

^aDepartment of Biology and Chemistry, Changzhi University, Changzhi, Shanxi 046011, People's Republic of China
^*Correspondence e-mail: jlwangczu@126.com

(Received 3 October 2009; accepted 9 October 2009; online 23 October 2009)

In the title compound, C₂₈H₂₂N₄O₄, the molecule lies on a crystallographic twofold axis. The quinoline ring is essentially planar (give max or rms deviation 0.0186 Å), and the dihedral angle between the quinoline ring and the central benzene ring is 19.1 (4)°. Intramolecular N—H⋯(N,O) and C—H⋯O hydrogen bonds contribute to the formation of the roughly planar configuration. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds, and weak π–π interactions between the pyridine rings and central benzene rings of the neighboring molecules [centroid–centroid separation = 3.9009 (6) Å].

Related literature

For background to the applications of amide-type acyclic polyethers, see: Guggi et al. (1977 ); Wen et al. (2002 ); West et al. (1992 ). For a related amide-type acyclic polyether structure, see: Wen et al. (2005 ).

Experimental

Crystal data

C₂₈H₂₂N₄O₄
M_r = 478.50
Orthorhombic, F d d 2
a = 32.648 (14) Å
b = 11.459 (4) Å
c = 12.516 (5) Å
V = 4682 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 K
0.20 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.982, T_max = 0.989
4687 measured reflections
1080 independent reflections
670 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.083
S = 1.00
1080 reflections
167 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −6.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.88 (4)	2.17 (4)	2.592 (5)	109 (3)
N2—H2A⋯N1	0.88 (4)	2.18 (4)	2.658 (5)	113 (3)
C7—H7⋯O1	0.93	2.32	2.915 (6)	121
C11—H11B⋯O1ⁱ	0.97	2.36	3.281 (6)	158
Symmetry code: (i) $[-x+{\script{1\over 4}}, y-{\script{1\over 4}}, z-{\script{1\over 4}}]$ .

Data collection: SMART (Bruker 2001 ); cell refinement: SAINT (Bruker 2001); data reduction: SAINT; 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: https://doi.org/10.1107/S1600536809041312/bq2164sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041312/bq2164Isup2.hkl

checkCIF report

Comment top

The amide-type acyclic polyethers have attracted wide attention in coordination chemistry and separation science because they have good complexing ability (West et al., 1992) and high selectivity to metal ions (Wen et al., 2002). In addition, this kind of compounds have been used successfully as active materials for ion-selective electrodes (Guggi et al., 1977). Here, we report the synthesis and structure of the title compound.

The asymmetric unit of (I) contains one half-molecule, the other half being related by a crystallographic twofold axis (Fig. 1). All bond lengths and angles in (I) are within normal ranges, and comparable with those in the related compound (Wen et al., 2005). The quinoline ring is essentially planar, with a dihedral angle of 2.1 (2)° between the benzene (C4—C9) ring and pyridine (C1—C4/C9/N1) ring. The dihedral angle between the quinoline ring and the central benzene ring is 19.1 (4)°. The amide N and C atoms are also planar configuration because the sum of the angles around atoms N2 and C10 are 359.3° and 360.0°, respectively. The intramolecular hydrogen bonds, N2—H2A···N1, N2—H2A···O2 and C7-H7···O1, form stable five- and six-membered rings, this being helpful to the formation of the planar configuration. The crystal packing is stabilized by intermolecular C11—H11B···O1 hydrogen bonds, and π-π interactions [short centroid-centroid separation = 3.9009 (6) Å] between the pyridine rings and central benzene rings of the neighboring molecules (Table 1 and Fig. 2).

Related literature top

For background to the applications of amide-type acyclic polyethers, see: Guggi et al. (1977); Wen et al. (2002); West et al. (1992). For a related amide-type acyclic polyether structure, see: Wen et al. (2005).

Experimental top

Compound (I) was prepared according to the literature method of Wen et al. (2005). Yellow single crystals suitable for an X-ray diffraction study were obtained by slow evaporation of a petroleum ether-ethyl acetate solution (1:3 v/v) over a period of 10 d.

Structure description top

For background to the applications of amide-type acyclic polyethers, see: Guggi et al. (1977); Wen et al. (2002); West et al. (1992). For a related amide-type acyclic polyether structure, see: Wen et al. (2005).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 20% probability displacement ellipsoids. [Symmetry code: (i) -x, 2-y, z].
	Fig. 2. The packing diagram of (I) viewed down c-axis. Intermolecular H-bonds are indicated by dashed lines. H atoms were omitted for clearance.

N,N'-Di-8-quinolyl-2,2'-(o-phenylenedioxy)diacetamide top

Crystal data top

C₂₈H₂₂N₄O₄	F(000) = 2000
M_r = 478.50	D_x = 1.358 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 925 reflections
a = 32.648 (14) Å	θ = 2.5–20.7°
b = 11.459 (4) Å	µ = 0.09 mm⁻¹
c = 12.516 (5) Å	T = 294 K
V = 4682 (3) Å³	Prism, yellow
Z = 8	0.20 × 0.14 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1080 independent reflections
Radiation source: fine-focus sealed tube	670 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −38→34
T_min = 0.982, T_max = 0.989	k = −12→13
4687 measured reflections	l = −14→11

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0372P)²] where P = (F_o² + 2F_c²)/3
1080 reflections	(Δ/σ)_max < 0.001
167 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₈H₂₂N₄O₄	V = 4682 (3) Å³
M_r = 478.50	Z = 8
Orthorhombic, Fdd2	Mo Kα radiation
a = 32.648 (14) Å	µ = 0.09 mm⁻¹
b = 11.459 (4) Å	T = 294 K
c = 12.516 (5) Å	0.20 × 0.14 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1080 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	670 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.989	R_int = 0.060
4687 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.15 e Å⁻³
1080 reflections	Δρ_min = −0.16 e Å⁻³
167 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.13016 (8)	1.0567 (3)	0.5394 (3)	0.0891 (10)
O2	0.03851 (7)	1.0165 (2)	0.39873 (19)	0.0631 (8)
N1	0.00878 (10)	0.8564 (3)	0.6781 (2)	0.0567 (8)
N2	0.07030 (10)	0.9673 (3)	0.5830 (3)	0.0588 (9)
C1	−0.02253 (12)	0.8058 (3)	0.7257 (3)	0.0617 (11)
H1	−0.0457	0.7900	0.6851	0.074*
C2	−0.02300 (13)	0.7745 (4)	0.8338 (4)	0.0695 (12)
H2	−0.0460	0.7392	0.8634	0.083*
C3	0.01028 (14)	0.7961 (4)	0.8944 (4)	0.0712 (12)
H3	0.0104	0.7760	0.9664	0.085*
C4	0.04461 (13)	0.8488 (3)	0.8485 (3)	0.0588 (10)
C5	0.08058 (15)	0.8758 (4)	0.9066 (4)	0.0772 (12)
H5	0.0827	0.8552	0.9783	0.093*
C6	0.11176 (16)	0.9313 (4)	0.8577 (4)	0.0818 (15)
H6	0.1352	0.9484	0.8968	0.098*
C7	0.11003 (13)	0.9644 (4)	0.7497 (4)	0.0717 (12)
H7	0.1319	1.0034	0.7182	0.086*
C8	0.07540 (11)	0.9384 (3)	0.6908 (3)	0.0562 (10)
C9	0.04230 (11)	0.8797 (3)	0.7402 (3)	0.0513 (10)
C10	0.09592 (12)	1.0223 (3)	0.5173 (3)	0.0599 (11)
C11	0.08113 (11)	1.0392 (3)	0.4046 (4)	0.0635 (11)
H11A	0.0866	1.1186	0.3818	0.076*
H11B	0.0957	0.9867	0.3571	0.076*
C12	0.02089 (10)	1.0103 (3)	0.2991 (3)	0.0583 (10)
C13	0.04141 (13)	1.0219 (3)	0.2046 (3)	0.0728 (12)
H13	0.0694	1.0369	0.2043	0.087*
C14	0.02013 (13)	1.0111 (4)	0.1088 (4)	0.0905 (17)
H14	0.0340	1.0194	0.0443	0.109*
H2A	0.0455 (12)	0.947 (3)	0.560 (3)	0.077 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0467 (16)	0.098 (2)	0.122 (2)	−0.0231 (15)	−0.007 (2)	0.003 (2)
O2	0.0432 (15)	0.086 (2)	0.0598 (18)	−0.0090 (13)	0.0050 (14)	−0.0031 (14)
N1	0.0398 (18)	0.055 (2)	0.075 (2)	0.0006 (16)	−0.0048 (18)	−0.0033 (16)
N2	0.036 (2)	0.065 (2)	0.075 (3)	−0.0069 (18)	−0.0018 (19)	−0.0029 (17)
C1	0.046 (3)	0.055 (2)	0.084 (3)	0.002 (2)	−0.004 (2)	−0.001 (2)
C2	0.068 (3)	0.061 (3)	0.080 (3)	0.002 (2)	0.012 (2)	−0.003 (2)
C3	0.087 (3)	0.062 (3)	0.064 (3)	0.011 (3)	0.002 (3)	−0.005 (2)
C4	0.060 (3)	0.049 (2)	0.067 (3)	0.009 (2)	−0.010 (2)	−0.0103 (19)
C5	0.090 (3)	0.068 (3)	0.073 (3)	0.010 (3)	−0.020 (3)	−0.006 (2)
C6	0.076 (4)	0.068 (3)	0.102 (4)	0.014 (3)	−0.045 (3)	−0.017 (3)
C7	0.053 (3)	0.066 (3)	0.097 (3)	0.000 (2)	−0.018 (2)	−0.008 (2)
C8	0.044 (3)	0.056 (2)	0.069 (3)	0.004 (2)	−0.010 (2)	−0.0128 (19)
C9	0.045 (2)	0.040 (2)	0.069 (3)	0.0099 (18)	−0.004 (2)	−0.0094 (19)
C10	0.040 (2)	0.053 (3)	0.087 (3)	0.001 (2)	0.005 (2)	−0.007 (2)
C11	0.043 (2)	0.060 (2)	0.088 (3)	−0.0094 (18)	0.011 (2)	0.000 (2)
C12	0.067 (2)	0.052 (2)	0.055 (2)	0.005 (2)	0.005 (2)	0.0020 (18)
C13	0.079 (3)	0.067 (3)	0.072 (3)	0.003 (2)	0.014 (3)	0.009 (2)
C14	0.124 (4)	0.087 (4)	0.061 (3)	0.024 (4)	0.013 (3)	0.005 (3)

Geometric parameters (Å, º) top

O1—C10	1.217 (4)	C5—C6	1.348 (6)
O2—C12	1.375 (4)	C5—H5	0.9300
O2—C11	1.417 (4)	C6—C7	1.406 (6)
N1—C1	1.317 (4)	C6—H6	0.9300
N1—C9	1.369 (4)	C7—C8	1.382 (5)
N2—C10	1.332 (5)	C7—H7	0.9300
N2—C8	1.399 (5)	C8—C9	1.415 (5)
N2—H2A	0.89 (4)	C10—C11	1.504 (5)
C1—C2	1.400 (5)	C11—H11A	0.9700
C1—H1	0.9300	C11—H11B	0.9700
C2—C3	1.348 (5)	C12—C13	1.366 (5)
C2—H2	0.9300	C12—C12ⁱ	1.384 (7)
C3—C4	1.397 (5)	C13—C14	1.391 (6)
C3—H3	0.9300	C13—H13	0.9300
C4—C9	1.403 (4)	C14—C14ⁱ	1.339 (9)
C4—C5	1.416 (5)	C14—H14	0.9300

C12—O2—C11	117.8 (3)	C6—C7—H7	120.4
C1—N1—C9	116.7 (3)	C7—C8—N2	124.1 (4)
C10—N2—C8	129.3 (4)	C7—C8—C9	119.6 (4)
C10—N2—H2A	120 (3)	N2—C8—C9	116.3 (3)
C8—N2—H2A	111 (3)	N1—C9—C4	122.9 (3)
N1—C1—C2	124.0 (4)	N1—C9—C8	117.1 (3)
N1—C1—H1	118.0	C4—C9—C8	120.1 (4)
C2—C1—H1	118.0	O1—C10—N2	126.1 (4)
C3—C2—C1	119.2 (4)	O1—C10—C11	117.8 (4)
C3—C2—H2	120.4	N2—C10—C11	116.0 (3)
C1—C2—H2	120.4	O2—C11—C10	109.9 (3)
C2—C3—C4	119.7 (4)	O2—C11—H11A	109.7
C2—C3—H3	120.2	C10—C11—H11A	109.7
C4—C3—H3	120.2	O2—C11—H11B	109.7
C3—C4—C9	117.6 (4)	C10—C11—H11B	109.7
C3—C4—C5	123.3 (4)	H11A—C11—H11B	108.2
C9—C4—C5	119.1 (4)	C13—C12—O2	125.1 (3)
C6—C5—C4	119.7 (4)	C13—C12—C12ⁱ	120.0 (2)
C6—C5—H5	120.1	O2—C12—C12ⁱ	114.91 (16)
C4—C5—H5	120.1	C12—C13—C14	119.5 (4)
C5—C6—C7	122.3 (4)	C12—C13—H13	120.2
C5—C6—H6	118.8	C14—C13—H13	120.2
C7—C6—H6	118.8	C14ⁱ—C14—C13	120.5 (2)
C8—C7—C6	119.2 (5)	C14ⁱ—C14—H14	119.8
C8—C7—H7	120.4	C13—C14—H14	119.8

C9—N1—C1—C2	−0.6 (6)	C3—C4—C9—C8	176.9 (4)
N1—C1—C2—C3	−0.2 (7)	C5—C4—C9—C8	−0.8 (5)
C1—C2—C3—C4	−0.3 (6)	C7—C8—C9—N1	179.8 (3)
C2—C3—C4—C9	1.5 (6)	N2—C8—C9—N1	0.4 (4)
C2—C3—C4—C5	179.2 (4)	C7—C8—C9—C4	0.3 (5)
C3—C4—C5—C6	−177.1 (4)	N2—C8—C9—C4	−179.1 (3)
C9—C4—C5—C6	0.6 (6)	C8—N2—C10—O1	1.7 (6)
C4—C5—C6—C7	0.1 (7)	C8—N2—C10—C11	179.5 (3)
C5—C6—C7—C8	−0.6 (7)	C12—O2—C11—C10	−170.3 (3)
C6—C7—C8—N2	179.8 (4)	O1—C10—C11—O2	−168.2 (3)
C6—C7—C8—C9	0.4 (6)	N2—C10—C11—O2	13.8 (4)
C10—N2—C8—C7	0.3 (6)	C11—O2—C12—C13	1.5 (5)
C10—N2—C8—C9	179.7 (3)	C11—O2—C12—C12ⁱ	−179.1 (4)
C1—N1—C9—C4	2.0 (5)	O2—C12—C13—C14	178.5 (3)
C1—N1—C9—C8	−177.4 (3)	C12ⁱ—C12—C13—C14	−0.9 (7)
C3—C4—C9—N1	−2.5 (5)	C12—C13—C14—C14ⁱ	−0.4 (8)
C5—C4—C9—N1	179.7 (3)

Symmetry code: (i) −x, −y+2, z.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₂N₄O₄
M_r	478.50
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	294
a, b, c (Å)	32.648 (14), 11.459 (4), 12.516 (5)
V (Å³)	4682 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick,1996)
T_min, T_max	0.982, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	4687, 1080, 670
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.083, 1.00
No. of reflections	1080
No. of parameters	167
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: SMART (Bruker 2001), SAINT (Bruker 2001), SHELXTL (Sheldrick, 2001).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guggi, M., Pretsch, E. & Simon, W. (1977). Anal. Chim. Acta, 91, 107–112. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wen, Y. H., Lahiri, S., Qin, Z., Wu, X. L. & Liu, W. S. (2002). J. Radioanal. Nucl. Chem. 253, 263–265. Web of Science CrossRef CAS Google Scholar
Wen, Y.-H., Li, M.-J., Zhang, S.-S. & Li, X.-M. (2005). Acta Cryst. E61, o3373–o3374. Web of Science CSD CrossRef IUCr Journals Google Scholar
West, S. J., Ozawa, S., Seller, K., Tan, S. S. & Simon, W. (1992). Anal. Chem. 64, 533–540. CrossRef CAS Web of Science Google Scholar