N,N′-Di-8-quinolyladipamide

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.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.120
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B   ..  O1      ..       2.66 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1
PLAT066_ALERT_1_G Predicted and Reported Transmissions Identical .          ?
PLAT128_ALERT_4_G Non-standard setting of Space-group P21/c   ....      P21/n

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

H atoms were positioned geometrically, with N—H = 0.86 Å and C—H = 0.95–0.99 Å, respectively, and constrained to ride on their parent atoms, with U_iso(H) = 1.2 U_eq(C,N).

Computing details

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

	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

Crystal data

C24H22N4O2	F(000) = 420
Mr = 398.46	Dx = 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) Å^3	0.24 × 0.20 × 0.12 mm
Z = 2

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0579P)^2 + 0.1339P] where P = (Fo^2 + 2Fc^2)/3
2048 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.14 e Å^−3
1 restraint	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C12^i	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—C12^i	112.39 (18)
C4—C5—H5	119.9	C11—C12—H12A	109.1
C5—C6—C7	121.21 (17)	C12^i—C12—H12A	109.1
C5—C6—H6	119.4	C11—C12—H12B	109.1
C7—C6—H6	119.4	C12^i—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—C12^i	176.88 (18)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

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···O1^ii	0.97	2.66	3.134 (2)	111

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