N,N′-Di-8-quinolyladipamide

Wang, S.-Y.; Xie, X.-L.; Huang, Q.-H.; Lin, Y.-S.

doi:10.1107/S1600536809017541

organic compounds

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Volume 65| Part 6| June 2009| Page o1399

doi:10.1107/S1600536809017541

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N,N′-Di-8-quinolyladipamide

Shi-Ying Wang,^a ^* Xing-Lei Xie,^a Qing-Hua Huang ^a and Yu-Sheng Lin ^a

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: wenyyhh@126.com

(Received 15 April 2009; accepted 11 May 2009; online 23 May 2009)

The complete molecule of the title compound, C₂₄H₂₂N₄O₂, is generated by a crystallographic inversion centre located at the mid-point of the central C—C bond. The quinoline ring system and the hexyl chain are both essentially planar, and the dihedral angle between them is 46.30 (2)°. Intramolecular N—H⋯N and C—H⋯O hydrogen bonds form five- and six-numbered rings, respectively. The crystal packing is stabilized by short C—H⋯O interactions.

Related literature

For details of the synthesis, see: Chen et al. (2007 ). For related structures, see: Chen et al. (2007); Wen et al. (2006 ).

Experimental

Crystal data

C₂₄H₂₂N₄O₂
M_r = 398.46
Monoclinic, P 2₁ /n
a = 9.923 (2) Å
b = 9.184 (2) Å
c = 11.722 (3) Å
β = 110.530 (4)°
V = 1000.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick,1996 ) T_min = 0.980, T_max = 0.990
5622 measured reflections
2048 independent reflections
1274 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.120
S = 1.00
2048 reflections
140 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1	0.892 (9)	2.23 (2)	2.676 (2)	110.4 (15)
C7—H7⋯O1	0.93	2.33	2.902 (2)	119
C11—H11B⋯O1ⁱ	0.97	2.66	3.134 (2)	111
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536809017541/fl2250sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017541/fl2250Isup2.hkl

checkCIF report

Comment top

Recently, Chen et al. (2007) reported the syntheses and crystal structures of the flexible ligand N,N'-di(2-pyridyl)adipamide and its several Ag(I) complexes. Theses complexes form topologically promising zigzag, helical or sinusoidal chain architectures because the flexible ligand can adopt three different conformations. To investigate the influence of the terminal groups on crystal structure, and to obtain a more topologically promising coordination framework, we synthesized and carried out the structure determination of the title compound, (I) (Fig. 1).

The molecule sits on a center of symmetry passing through the central C12—C12ⁱⁱ bond [symmetry code: (ii): -x, -y, -z] (Fig. 1). All bond lengths and angles in (I) show normal values and are comparable to those of the related compounds, N,N'-di(2-pyridyl)adipamide (Chen et al., 2007), and N-(quinolin-8-yl)-2-(quinolin-8-yloxy)acetamide (Wen et al., 2006). The quinoline group is essentially planar, with a dihedral angle of 1.70 (3)° between the benzene ring (C4—C9) and pyridine ring (C1—C4/C9/N1). The C10—C12/C10A—C12A unit is also planar, with the dihedral angle to the quinoline system of 46.30 (2)°. Two intramolecular hydrogen bonds, viz. N2—H2A···N1 and C7—H7···O1 (Fig. 1 and Table 1), form five- and six-membered rings, respectively, and affect the conformation of the molecule. The crystal packing is stabilized by short C11—H11B···O1 interactions (Fig. 2 and Table 1).

Related literature top

For details of the synthesis, see: Chen et al. (2007). For related structures, see: Chen et al. (2007); Wen et al. (2006).

Experimental top

The title compound was synthesized by a reaction of adipoyl chloride and 8-aminoquinoline according to literature method (Chen et al., 2007). Colourless single cystals suitable for X-ray diffraction were obtained by slow evaporation from a methanol solution over a period of 7 d.

Computing details top

Data collection: SMART (Bruker 2001); cell refinement: SAINT (Bruker 2001); data reduction: SAINT (Bruker 2001); 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 (I), with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. The packing diagram of (I), viewed down the b axis.

N,N'-Di-8-quinolyladipamide top

Crystal data top

C₂₄H₂₂N₄O₂	F(000) = 420
M_r = 398.46	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1501 reflections
a = 9.923 (2) Å	θ = 2.9–25.3°
b = 9.184 (2) Å	µ = 0.09 mm⁻¹
c = 11.722 (3) Å	T = 294 K
β = 110.530 (4)°	Column, colourless
V = 1000.4 (4) Å³	0.24 × 0.20 × 0.12 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2048 independent reflections
Radiation source: fine-focus sealed tube	1274 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −11→12
T_min = 0.980, T_max = 0.990	k = −11→9
5622 measured reflections	l = −9→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0579P)² + 0.1339P] where P = (F_o² + 2F_c²)/3
2048 reflections	(Δ/σ)_max < 0.001
140 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₄H₂₂N₄O₂	V = 1000.4 (4) Å³
M_r = 398.46	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.923 (2) Å	µ = 0.09 mm⁻¹
b = 9.184 (2) Å	T = 294 K
c = 11.722 (3) Å	0.24 × 0.20 × 0.12 mm
β = 110.530 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2048 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	1274 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.032
5622 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.14 e Å⁻³
2048 reflections	Δρ_min = −0.17 e Å⁻³
140 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	0.31418 (15)	−0.13777 (14)	0.23248 (14)	0.0793 (5)
N1	0.61637 (15)	0.28926 (17)	0.28795 (13)	0.0498 (4)
N2	0.41475 (15)	0.08554 (16)	0.26119 (14)	0.0440 (4)
C1	0.7142 (2)	0.3904 (2)	0.30187 (19)	0.0626 (6)
H1	0.6886	0.4723	0.2522	0.075*
C2	0.8543 (2)	0.3835 (3)	0.38633 (19)	0.0649 (6)
H2	0.9192	0.4585	0.3917	0.078*
C3	0.8942 (2)	0.2662 (2)	0.46005 (17)	0.0559 (5)
H3	0.9869	0.2602	0.5172	0.067*
C4	0.79507 (17)	0.1532 (2)	0.45011 (15)	0.0438 (5)
C5	0.82757 (19)	0.0257 (2)	0.52156 (17)	0.0518 (5)
H5	0.9178	0.0148	0.5816	0.062*
C6	0.72814 (19)	−0.0807 (2)	0.50313 (17)	0.0529 (5)
H6	0.7518	−0.1654	0.5494	0.063*
C7	0.59014 (19)	−0.0659 (2)	0.41559 (16)	0.0475 (5)
H7	0.5236	−0.1407	0.4044	0.057*
C8	0.55222 (17)	0.05739 (19)	0.34647 (15)	0.0390 (4)
C9	0.65611 (17)	0.16955 (18)	0.36128 (14)	0.0391 (4)
C10	0.30407 (18)	−0.0079 (2)	0.21278 (16)	0.0455 (5)
C11	0.16598 (18)	0.06244 (19)	0.13495 (17)	0.0477 (5)
H11A	0.1883	0.1489	0.0975	0.057*
H11B	0.1132	0.0930	0.1866	0.057*
C12	0.07120 (17)	−0.03564 (19)	0.03641 (16)	0.0447 (5)
H12A	0.0526	−0.1245	0.0731	0.054*
H12B	0.1214	−0.0618	−0.0183	0.054*
H2A	0.4032 (19)	0.1789 (11)	0.2388 (17)	0.057 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0648 (10)	0.0370 (8)	0.0939 (12)	−0.0048 (7)	−0.0250 (8)	0.0065 (8)
N1	0.0425 (9)	0.0574 (10)	0.0425 (9)	−0.0107 (8)	0.0061 (7)	0.0051 (8)
N2	0.0328 (8)	0.0376 (9)	0.0489 (9)	−0.0033 (6)	−0.0017 (7)	0.0043 (7)
C1	0.0590 (13)	0.0706 (14)	0.0506 (12)	−0.0212 (11)	0.0096 (10)	0.0115 (10)
C2	0.0532 (13)	0.0802 (15)	0.0543 (12)	−0.0290 (11)	0.0100 (10)	−0.0005 (11)
C3	0.0382 (10)	0.0782 (14)	0.0444 (11)	−0.0126 (10)	0.0058 (8)	−0.0063 (11)
C4	0.0344 (10)	0.0587 (12)	0.0354 (9)	−0.0033 (8)	0.0087 (8)	−0.0069 (9)
C5	0.0343 (10)	0.0684 (13)	0.0427 (10)	0.0058 (9)	0.0012 (8)	0.0007 (10)
C6	0.0446 (11)	0.0561 (12)	0.0479 (11)	0.0067 (9)	0.0037 (9)	0.0073 (9)
C7	0.0396 (10)	0.0478 (11)	0.0475 (11)	−0.0017 (8)	0.0060 (9)	0.0023 (9)
C8	0.0315 (9)	0.0452 (10)	0.0363 (9)	−0.0001 (7)	0.0068 (7)	−0.0019 (8)
C9	0.0347 (9)	0.0476 (10)	0.0334 (9)	−0.0005 (8)	0.0099 (8)	−0.0023 (8)
C10	0.0393 (10)	0.0374 (10)	0.0478 (10)	−0.0042 (8)	0.0005 (8)	−0.0004 (8)
C11	0.0379 (10)	0.0404 (10)	0.0521 (11)	−0.0023 (8)	0.0000 (9)	−0.0006 (9)
C12	0.0333 (10)	0.0419 (10)	0.0485 (10)	−0.0030 (7)	0.0014 (8)	0.0006 (8)

Geometric parameters (Å, º) top

O1—C10	1.213 (2)	C5—C6	1.351 (3)
N1—C1	1.312 (2)	C5—H5	0.9300
N1—C9	1.366 (2)	C6—C7	1.400 (2)
N2—C10	1.352 (2)	C6—H6	0.9300
N2—C8	1.404 (2)	C7—C8	1.366 (2)
N2—H2A	0.892 (9)	C7—H7	0.9300
C1—C2	1.397 (3)	C8—C9	1.424 (2)
C1—H1	0.9300	C10—C11	1.500 (2)
C2—C3	1.350 (3)	C11—C12	1.506 (2)
C2—H2	0.9300	C11—H11A	0.9700
C3—C4	1.407 (2)	C11—H11B	0.9700
C3—H3	0.9300	C12—C12ⁱ	1.519 (3)
C4—C5	1.410 (3)	C12—H12A	0.9700
C4—C9	1.415 (2)	C12—H12B	0.9700

C1—N1—C9	117.01 (16)	C8—C7—H7	119.7
C10—N2—C8	128.73 (15)	C6—C7—H7	119.7
C10—N2—H2A	119.0 (12)	C7—C8—N2	124.88 (16)
C8—N2—H2A	112.2 (12)	C7—C8—C9	119.34 (15)
N1—C1—C2	124.37 (19)	N2—C8—C9	115.76 (15)
N1—C1—H1	117.8	N1—C9—C4	122.70 (15)
C2—C1—H1	117.8	N1—C9—C8	117.95 (15)
C3—C2—C1	119.07 (18)	C4—C9—C8	119.36 (15)
C3—C2—H2	120.5	O1—C10—N2	122.93 (16)
C1—C2—H2	120.5	O1—C10—C11	122.42 (15)
C2—C3—C4	119.71 (18)	N2—C10—C11	114.63 (15)
C2—C3—H3	120.1	C10—C11—C12	113.62 (15)
C4—C3—H3	120.1	C10—C11—H11A	108.8
C3—C4—C5	123.78 (17)	C12—C11—H11A	108.8
C3—C4—C9	117.12 (17)	C10—C11—H11B	108.8
C5—C4—C9	119.08 (16)	C12—C11—H11B	108.8
C6—C5—C4	120.26 (17)	H11A—C11—H11B	107.7
C6—C5—H5	119.9	C11—C12—C12ⁱ	112.39 (18)
C4—C5—H5	119.9	C11—C12—H12A	109.1
C5—C6—C7	121.21 (17)	C12ⁱ—C12—H12A	109.1
C5—C6—H6	119.4	C11—C12—H12B	109.1
C7—C6—H6	119.4	C12ⁱ—C12—H12B	109.1
C8—C7—C6	120.70 (17)	H12A—C12—H12B	107.9

C9—N1—C1—C2	−0.3 (3)	C1—N1—C9—C8	−179.10 (17)
N1—C1—C2—C3	−0.3 (3)	C3—C4—C9—N1	−0.7 (2)
C1—C2—C3—C4	0.5 (3)	C5—C4—C9—N1	−179.61 (16)
C2—C3—C4—C5	178.89 (19)	C3—C4—C9—C8	179.22 (16)
C2—C3—C4—C9	0.0 (3)	C5—C4—C9—C8	0.3 (2)
C3—C4—C5—C6	−177.26 (18)	C7—C8—C9—N1	177.82 (16)
C9—C4—C5—C6	1.6 (3)	N2—C8—C9—N1	−3.5 (2)
C4—C5—C6—C7	−1.7 (3)	C7—C8—C9—C4	−2.1 (2)
C5—C6—C7—C8	−0.2 (3)	N2—C8—C9—C4	176.61 (15)
C6—C7—C8—N2	−176.52 (17)	C8—N2—C10—O1	−5.4 (3)
C6—C7—C8—C9	2.1 (3)	C8—N2—C10—C11	173.11 (17)
C10—N2—C8—C7	−14.2 (3)	O1—C10—C11—C12	−30.0 (3)
C10—N2—C8—C9	167.19 (17)	N2—C10—C11—C12	151.44 (17)
C1—N1—C9—C4	0.8 (3)	C10—C11—C12—C12ⁱ	176.88 (18)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.89 (1)	2.23 (2)	2.676 (2)	110 (2)
C7—H7···O1	0.93	2.33	2.902 (2)	119
C11—H11B···O1ⁱⁱ	0.97	2.66	3.134 (2)	111

Symmetry code: (ii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂N₄O₂
M_r	398.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	9.923 (2), 9.184 (2), 11.722 (3)
β (°)	110.530 (4)
V (Å³)	1000.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick,1996)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	5622, 2048, 1274
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.120, 1.00
No. of reflections	2048
No. of parameters	140
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)	0.14, −0.17

Computer programs: SMART (Bruker 2001), SAINT (Bruker 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.892 (9)	2.23 (2)	2.676 (2)	110.4 (15)
C7—H7···O1	0.93	2.33	2.902 (2)	119.0
C11—H11B···O1ⁱ	0.97	2.656	3.134 (2)	110.7

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the Outstanding Adult-Young Scientific Research Encouraging Foundation of Shandong Province, China (No. 2008BS0901) and the Natural Science Foundation of Shandong Province (No. Y2007B50).

References

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