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The title compound, C15H11N3O, is basically planar except that the pyridine ring is slightly titled, the dihedral angle between the pyridyl and quinolyl rings being 3.55 (5)°. The crystal grows in two directions and the crystal packing is stabilized by π–π stacking interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100015158/na1484sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100015158/na1484Isup2.hkl
Contains datablock I

CCDC reference: 158275

Comment top

Quinoxaline derivatives, such as XK469, showed unusual solid-tumor selectivity and activity against multidrug-resistant cancer cells (Gao et al., 1999). Some platinum complexes of pyridine and quinoline ligands, such as trans-dichlorodipyridineplatinum(II) and trans-amminedichloroquinolineplatinum(II), show comparable anticancer activity to cisplatin in cisplatin-sensitive and -resistant cell lines (Wong & Giandomenico, 1999). Moreover, some metallointercalators have been widely used in DNA structural and mechanistic studies (Erkkila et al., 1999). The aminoquinoline-based ligands possess strong fluorescent property which could be used as a probe for DNA binding (Fahrni and O'halloran, 1999; Nasir et al., 1999). Therefore, we synthesized the title compound, (I), in order to investigate their binding ability towards metal ions and DNA. This ligand contains pyridine, amide and quinoline nitrogen atoms which are able to coordinate to metal ions, such as ZnII and CuII (Fahrni and O'halloran, 1999; Nasir et al., 1999; Amendola et al., 1999). Studies of the metal complexes of the ligand will be reported elsewhere. \scheme

The X-ray crystallographic study shows that both lengths and angles are within the normal ranges. The N2—C6 and N2—C7 bond distances in (I) are comparable to those in [N,N'-bis(2-pyridinecarboxamido)-1,2-benzene]copper(II) [1.337 (3) and 1.404 (2) Å; Chapman et al., 1980] and N,N'-(4,5-dichloro-o-phenylene)bis(4-tert-butylpyridine-2-carboxamide) [1.350 (4) and 1.401 (4) Å; Fun et al., 1999), while the C—C and CO bond lengths are similar to those reported in [N,N'-bis(2-pyridinecarboxamide)-1,2-benzene]nickel(II) monohydrate (Stephens & Vagg, 1986). The molecule of (I) is almost planar, except that the pyridyl ring is slightly tilted, the dihedral angle between pyridyl and quinolyl rings being 3.55 (5)°. There are four intramolecular hydrogen bonds in the crystal (see Table 2) which could be the driving force to have N1 and N3 in the same side of the molecule.

The crystal is a thin plate and grows in two different directions which cross each other and the angle between these two orientations is 60.8°. There is a ππ stacking interaction between the adjacent molecules packed in the same direction. The distance between the two adjacent parallel aromatic rings [C1–C5/N1 and C7i–C11i/C15i; symmetry code: (i) 1 - x, 2 - y,-z] is 3.68 (2) Å, and the shortest distance is C2···C9i of 3.481 (4) Å. This kind of interaction belongs to the face-to-face type, with a little offset, and the molecules are arranged in a head-to-tail fashion, i.e. the pyridyl group faces the quinoline group.

In order to understand the electron-donating ability of the three N atoms, ab initio calculations (method HF/3–21g*) in GAUSSIAN98 (Frisch et al., 1998) were carried out. This gave rise to electron-distribution values of -0.731 e, -1.095 e and -0.746 e for N1, N2 and N3, respectively.

Experimental top

The title compound was obtained by the reaction of one molar equivalent of pyridine-2-carboxylic acid and 8-aminoquinoline in the presence of one molar equivalent of triphenyl phosphite in pyridine at 473 K for 4 h (Leung et al., 1991). Single crystals suitable for X-ray diffraction were recrystallized from pyridine and ethanol.

Refinement top

All H atoms were placed in geometrically calculated positions (C—H = 0.93 Å and N—H = 0.86 Å), with Uiso = 1.2Ueq(parent atom).

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL(Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.
N-(8-quinolyl)-2-pyridinecarboxamide top
Crystal data top
C15H11N3OF(000) = 520
Mr = 249.27Dx = 1.354 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.677 (2) ÅCell parameters from 41 reflections
b = 7.915 (3) Åθ = 5.2–15.1°
c = 20.408 (5) ŵ = 0.09 mm1
β = 99.64 (2)°T = 293 K
V = 1222.5 (6) Å3Thick plate, colorless
Z = 40.50 × 0.50 × 0.40 mm
Data collection top
Siemens P4
diffractometer
1406 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.026
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
2θ/ω scansh = 19
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
k = 19
Tmin = 0.956, Tmax = 0.965l = 2424
3082 measured reflections3 standard reflections every 97 reflections
2149 independent reflections intensity decay: 7.1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0531P)2 + 0.0469P]
where P = (Fo2 + 2Fc2)/3
2149 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C15H11N3OV = 1222.5 (6) Å3
Mr = 249.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.677 (2) ŵ = 0.09 mm1
b = 7.915 (3) ÅT = 293 K
c = 20.408 (5) Å0.50 × 0.50 × 0.40 mm
β = 99.64 (2)°
Data collection top
Siemens P4
diffractometer
1406 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
Rint = 0.026
Tmin = 0.956, Tmax = 0.9653 standard reflections every 97 reflections
3082 measured reflections intensity decay: 7.1%
2149 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.07Δρmax = 0.17 e Å3
2149 reflectionsΔρmin = 0.16 e Å3
172 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
xyzUiso*/Ueq
O10.20798 (18)0.7992 (2)0.01580 (7)0.0709 (5)
N10.6691 (2)0.7271 (2)0.01886 (8)0.0547 (5)
N20.4150 (2)0.8663 (2)0.07432 (7)0.0496 (4)
H2B0.52610.85760.08930.060*
N30.5875 (2)0.9591 (2)0.19282 (8)0.0569 (5)
C10.7989 (3)0.6621 (3)0.00868 (11)0.0645 (6)
H1A0.91240.66320.01590.077*
C20.7751 (3)0.5928 (3)0.07184 (12)0.0698 (7)
H2A0.87010.54850.08910.084*
C30.6099 (3)0.5910 (3)0.10802 (11)0.0676 (6)
H3A0.58980.54500.15060.081*
C40.4720 (3)0.6580 (3)0.08092 (10)0.0590 (6)
H4A0.35760.65830.10480.071*
C50.5076 (2)0.7247 (2)0.01761 (9)0.0461 (5)
C60.3611 (3)0.7997 (3)0.01303 (9)0.0494 (5)
C70.3154 (2)0.9474 (2)0.11667 (9)0.0467 (5)
C80.1381 (2)0.9819 (3)0.10156 (10)0.0549 (5)
H8A0.07460.94910.06070.066*
C90.0517 (3)1.0666 (3)0.14763 (11)0.0641 (6)
H9A0.06891.08780.13680.077*
C100.1402 (3)1.1180 (3)0.20734 (11)0.0620 (6)
H10A0.08071.17440.23690.074*
C110.3241 (3)1.0855 (3)0.22468 (10)0.0531 (5)
C120.4277 (3)1.1372 (3)0.28501 (11)0.0667 (6)
H12A0.37591.19660.31610.080*
C130.6033 (3)1.1003 (3)0.29791 (11)0.0736 (7)
H13A0.67291.13440.33740.088*
C140.6763 (3)1.0095 (3)0.25017 (10)0.0706 (7)
H14A0.79590.98310.25970.085*
C150.4114 (2)0.9977 (3)0.17963 (9)0.0469 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0489 (9)0.0973 (13)0.0616 (9)0.0062 (9)0.0048 (7)0.0098 (9)
N10.0447 (10)0.0606 (12)0.0595 (10)0.0006 (9)0.0103 (8)0.0011 (8)
N20.0430 (9)0.0589 (11)0.0458 (9)0.0045 (8)0.0045 (7)0.0022 (8)
N30.0490 (10)0.0721 (13)0.0493 (10)0.0010 (9)0.0072 (8)0.0012 (9)
C10.0493 (12)0.0711 (16)0.0744 (15)0.0034 (12)0.0143 (11)0.0004 (13)
C20.0755 (16)0.0657 (16)0.0746 (15)0.0099 (13)0.0311 (13)0.0005 (13)
C30.0886 (17)0.0640 (15)0.0517 (13)0.0073 (14)0.0156 (12)0.0019 (11)
C40.0655 (13)0.0598 (14)0.0503 (12)0.0040 (12)0.0055 (10)0.0007 (11)
C50.0513 (11)0.0434 (11)0.0440 (10)0.0032 (10)0.0090 (9)0.0059 (9)
C60.0492 (12)0.0507 (12)0.0468 (11)0.0000 (10)0.0035 (9)0.0063 (10)
C70.0486 (11)0.0446 (12)0.0476 (10)0.0044 (10)0.0104 (9)0.0075 (9)
C80.0496 (12)0.0630 (14)0.0511 (11)0.0070 (11)0.0057 (9)0.0081 (11)
C90.0545 (12)0.0733 (16)0.0666 (14)0.0174 (12)0.0165 (11)0.0138 (12)
C100.0637 (14)0.0599 (15)0.0672 (14)0.0148 (12)0.0254 (12)0.0064 (11)
C110.0656 (13)0.0463 (12)0.0504 (11)0.0001 (11)0.0184 (10)0.0043 (10)
C120.0842 (17)0.0598 (15)0.0592 (13)0.0058 (13)0.0210 (12)0.0062 (11)
C130.0789 (17)0.0851 (19)0.0557 (13)0.0134 (15)0.0081 (12)0.0121 (13)
C140.0583 (13)0.0947 (19)0.0567 (13)0.0092 (14)0.0039 (11)0.0083 (13)
C150.0479 (11)0.0467 (12)0.0478 (11)0.0001 (10)0.0122 (9)0.0063 (9)
Geometric parameters (Å, º) top
O1—C61.223 (2)C5—C61.498 (3)
N1—C11.327 (3)C7—C81.372 (3)
N1—C51.335 (2)C7—C151.427 (3)
N2—C61.357 (2)C8—C91.408 (3)
N2—C71.401 (2)C9—C101.355 (3)
N3—C141.314 (2)C10—C111.420 (3)
N3—C151.368 (2)C11—C121.410 (3)
C1—C21.384 (3)C11—C151.408 (3)
C2—C31.357 (3)C12—C131.361 (3)
C3—C41.380 (3)C13—C141.401 (3)
C4—C51.380 (3)
C1—N1—C5116.9 (2)C8—C7—C15119.4 (2)
C6—N2—C7129.3 (2)N2—C7—C15115.5 (2)
C14—N3—C15117.1 (2)C7—C8—C9120.4 (2)
N1—C1—C2123.8 (2)C10—C9—C8121.5 (2)
C3—C2—C1118.5 (2)C9—C10—C11119.9 (2)
C2—C3—C4119.2 (2)C12—C11—C15116.9 (2)
C5—C4—C3118.5 (2)C12—C11—C10123.8 (2)
N1—C5—C4123.2 (2)C15—C11—C10119.2 (2)
N1—C5—C6117.0 (2)C13—C12—C11120.1 (2)
C4—C5—C6119.8 (2)C12—C13—C14118.3 (2)
O1—C6—N2124.4 (2)N3—C14—C13124.5 (2)
O1—C6—C5121.7 (2)N3—C15—C11123.0 (2)
N2—C6—C5113.9 (2)N3—C15—C7117.3 (2)
C8—C7—N2125.1 (2)C11—C15—C7119.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···N10.862.212.653 (2)112
N2—H2B···N30.862.242.659 (2)110
C4—H4A···O10.932.562.833 (3)97
C8—H8A···O10.932.332.923 (3)121

Experimental details

Crystal data
Chemical formulaC15H11N3O
Mr249.27
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)7.677 (2), 7.915 (3), 20.408 (5)
β (°) 99.64 (2)
V3)1222.5 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.50 × 0.50 × 0.40
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(North et al., 1968)
Tmin, Tmax0.956, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections
3082, 2149, 1406
Rint0.026
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.122, 1.07
No. of reflections2149
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.16

Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL(Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
O1—C61.223 (2)N2—C71.401 (2)
N1—C11.327 (3)N3—C141.314 (2)
N1—C51.335 (2)N3—C151.368 (2)
N2—C61.357 (2)C5—C61.498 (3)
C1—N1—C5116.9 (2)C4—C5—C6119.8 (2)
C6—N2—C7129.3 (2)O1—C6—N2124.4 (2)
C14—N3—C15117.1 (2)O1—C6—C5121.7 (2)
N1—C5—C6117.0 (2)N2—C6—C5113.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···N10.862.212.653 (2)112
N2—H2B···N30.862.242.659 (2)110
C4—H4A···O10.932.562.833 (3)97
C8—H8A···O10.932.332.923 (3)121
 

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