N-(Quinolin-8-yl)quinoline-2-carbox-amide.

In the title compound, C(19)H(13)N(3)O, the dihedral angle between the two quinoline systems is 11.54 (3)°. The mol-ecular conformation is stabilized by intra-molecular N-H⋯N and C-H⋯O hydrogen bonds, with N-H⋯N being bifurcated towards the two N atoms of the two quinoline rings. In the crystal, there are weak intermolecular π-π inter-actions present involving the quinoline rings [centroid-centroid distance 3.7351 (14) Å].

Related literature

For the synthesis of the title compound and related structures, see: Kim et al. (2009 ▶). For applications of the title compound and background to the synthesis, see: Wang et al. (2011 ▶).

Experimental

Crystal data

C19H13N3O

M = 299.32

Orthorhombic,

a = 6.3651 (13) Å

b = 11.475 (2) Å

c = 19.861 (4) Å

V = 1450.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.25 × 0.15 × 0.15 mm

Data collection

Rigaku Saturn 724 CCD diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.978, T max = 0.987

6769 measured reflections

1553 independent reflections

1442 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.082

S = 1.06

1553 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020144/zl2476sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020144/zl2476Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020144/zl2476Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H13N3O	F(000) = 624
Mr = 299.32	Dx = 1.371 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac2ab	Cell parameters from 6054 reflections
a = 6.3651 (13) Å	θ = 3.4–29.0°
b = 11.475 (2) Å	µ = 0.09 mm−1
c = 19.861 (4) Å	T = 173 K
V = 1450.6 (5) Å3	Block, yellow
Z = 4	0.25 × 0.15 × 0.15 mm

Rigaku Saturn 724 CCD diffractometer	1553 independent reflections
Radiation source: Rotating Anode	1442 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.3°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→6
Tmin = 0.978, Tmax = 0.987	k = −13→13
6769 measured reflections	l = −23→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0494P)2] where P = (Fo2 + 2Fc2)/3
1553 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.10 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	−0.0149 (2)	0.41328 (13)	0.73413 (7)	0.0458 (4)
N1	−0.1752 (2)	0.46907 (14)	0.56729 (8)	0.0328 (4)
C1	−0.3327 (3)	0.44137 (16)	0.52317 (10)	0.0309 (4)
N2	0.1160 (2)	0.54135 (14)	0.65635 (8)	0.0336 (4)
H2A	0.0898	0.5707	0.6163	0.040*
C2	−0.3099 (3)	0.47410 (18)	0.45477 (10)	0.0367 (5)
H2	−0.1874	0.5146	0.4407	0.044*
N3	0.3570 (3)	0.69181 (14)	0.58750 (8)	0.0385 (4)
C3	−0.4630 (3)	0.44780 (19)	0.40896 (10)	0.0405 (5)
H3	−0.4453	0.4691	0.3631	0.049*
C4	−0.6456 (3)	0.38961 (18)	0.42926 (11)	0.0416 (5)
H4	−0.7514	0.3724	0.3970	0.050*
C5	−0.6737 (3)	0.35718 (18)	0.49498 (10)	0.0390 (5)
H5	−0.7993	0.3187	0.5082	0.047*
C6	−0.5164 (3)	0.38082 (16)	0.54318 (10)	0.0324 (5)
C7	−0.5302 (3)	0.34377 (17)	0.61049 (10)	0.0364 (5)
H7	−0.6505	0.3024	0.6257	0.044*
C8	−0.3693 (3)	0.36763 (17)	0.65394 (10)	0.0358 (5)
H8	−0.3739	0.3413	0.6993	0.043*
C9	−0.1960 (3)	0.43222 (16)	0.62995 (10)	0.0317 (5)
C10	−0.0232 (3)	0.46113 (17)	0.67895 (10)	0.0329 (4)
C11	0.2965 (3)	0.58357 (17)	0.68860 (10)	0.0322 (5)
C12	0.3571 (3)	0.55062 (19)	0.75238 (9)	0.0362 (5)
H12	0.2716	0.4994	0.7781	0.043*
C13	0.5465 (3)	0.59343 (19)	0.77909 (10)	0.0409 (6)
H13	0.5880	0.5697	0.8229	0.049*
C14	0.6721 (3)	0.66767 (18)	0.74419 (10)	0.0388 (5)
H14	0.7999	0.6945	0.7635	0.047*
C15	0.6127 (3)	0.70472 (17)	0.67950 (10)	0.0341 (5)
C16	0.7326 (3)	0.78261 (18)	0.64020 (11)	0.0404 (5)
H16	0.8604	0.8134	0.6572	0.049*
C17	0.6643 (4)	0.81326 (18)	0.57795 (11)	0.0423 (5)
H17	0.7423	0.8667	0.5513	0.051*
C18	0.4767 (4)	0.76476 (18)	0.55348 (10)	0.0436 (6)
H18	0.4330	0.7860	0.5094	0.052*
C19	0.4227 (3)	0.66226 (17)	0.65098 (10)	0.0315 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0481 (9)	0.0504 (9)	0.0389 (9)	−0.0030 (8)	−0.0031 (8)	0.0133 (7)
N1	0.0336 (9)	0.0318 (9)	0.0328 (9)	0.0016 (8)	0.0003 (8)	−0.0013 (7)
C1	0.0303 (10)	0.0286 (10)	0.0337 (10)	0.0012 (9)	0.0019 (9)	−0.0059 (8)
N2	0.0334 (9)	0.0372 (9)	0.0301 (8)	−0.0003 (8)	−0.0032 (8)	0.0028 (7)
C2	0.0339 (11)	0.0405 (12)	0.0356 (11)	−0.0021 (11)	0.0030 (9)	−0.0031 (9)
N3	0.0466 (10)	0.0354 (9)	0.0335 (9)	−0.0013 (9)	−0.0026 (9)	0.0011 (7)
C3	0.0426 (12)	0.0425 (12)	0.0366 (11)	0.0039 (11)	−0.0025 (10)	−0.0047 (10)
C4	0.0383 (12)	0.0374 (12)	0.0492 (14)	0.0031 (11)	−0.0089 (11)	−0.0080 (10)
C5	0.0342 (11)	0.0317 (11)	0.0512 (14)	−0.0025 (11)	−0.0032 (10)	−0.0044 (10)
C6	0.0317 (11)	0.0257 (10)	0.0397 (11)	0.0023 (9)	0.0021 (9)	−0.0040 (8)
C7	0.0357 (11)	0.0287 (10)	0.0448 (12)	0.0019 (10)	0.0075 (10)	−0.0004 (9)
C8	0.0393 (11)	0.0314 (10)	0.0367 (11)	0.0020 (10)	0.0046 (10)	0.0003 (9)
C9	0.0343 (11)	0.0276 (10)	0.0332 (11)	0.0046 (9)	0.0032 (9)	−0.0015 (8)
C10	0.0328 (11)	0.0327 (10)	0.0332 (10)	0.0056 (10)	0.0031 (9)	−0.0010 (9)
C11	0.0324 (11)	0.0337 (10)	0.0307 (11)	0.0043 (10)	−0.0002 (9)	−0.0053 (8)
C12	0.0385 (11)	0.0417 (12)	0.0283 (10)	0.0031 (11)	0.0018 (10)	−0.0015 (9)
C13	0.0418 (12)	0.0510 (14)	0.0300 (11)	0.0074 (12)	−0.0052 (10)	−0.0054 (9)
C14	0.0352 (11)	0.0462 (13)	0.0350 (12)	0.0071 (11)	−0.0055 (10)	−0.0104 (10)
C15	0.0360 (11)	0.0332 (10)	0.0330 (10)	0.0030 (10)	0.0024 (9)	−0.0092 (9)
C16	0.0402 (12)	0.0358 (11)	0.0454 (13)	−0.0030 (11)	0.0036 (10)	−0.0139 (10)
C17	0.0496 (14)	0.0350 (11)	0.0423 (13)	−0.0087 (11)	0.0051 (11)	−0.0044 (9)
C18	0.0563 (14)	0.0372 (12)	0.0374 (11)	−0.0050 (12)	−0.0009 (11)	0.0031 (9)
C19	0.0336 (10)	0.0313 (10)	0.0295 (10)	0.0053 (9)	0.0008 (9)	−0.0052 (8)

O1—C10	1.227 (2)	C7—H7	0.9500
N1—C9	1.321 (2)	C8—C9	1.412 (3)
N1—C1	1.369 (2)	C8—H8	0.9500
C1—C2	1.417 (3)	C9—C10	1.505 (3)
C1—C6	1.417 (3)	C11—C12	1.377 (3)
N2—C10	1.354 (3)	C11—C19	1.421 (3)
N2—C11	1.402 (2)	C12—C13	1.406 (3)
N2—H2A	0.8800	C12—H12	0.9500
C2—C3	1.367 (3)	C13—C14	1.358 (3)
C2—H2	0.9500	C13—H13	0.9500
N3—C18	1.318 (3)	C14—C15	1.405 (3)
N3—C19	1.371 (2)	C14—H14	0.9500
C3—C4	1.400 (3)	C15—C16	1.411 (3)
C3—H3	0.9500	C15—C19	1.421 (3)
C4—C5	1.369 (3)	C16—C17	1.357 (3)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.412 (3)	C17—C18	1.405 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.405 (3)	C18—H18	0.9500
C7—C8	1.367 (3)
C9—N1—C1	117.09 (17)	C8—C9—C10	117.92 (17)
N1—C1—C2	118.50 (18)	O1—C10—N2	124.89 (19)
N1—C1—C6	122.59 (17)	O1—C10—C9	120.68 (19)
C2—C1—C6	118.90 (18)	N2—C10—C9	114.42 (16)
C10—N2—C11	128.30 (17)	C12—C11—N2	123.71 (19)
C10—N2—H2A	115.8	C12—C11—C19	120.01 (19)
C11—N2—H2A	115.8	N2—C11—C19	116.26 (17)
C3—C2—C1	120.5 (2)	C11—C12—C13	119.4 (2)
C3—C2—H2	119.8	C11—C12—H12	120.3
C1—C2—H2	119.8	C13—C12—H12	120.3
C18—N3—C19	116.89 (19)	C14—C13—C12	122.1 (2)
C2—C3—C4	120.37 (19)	C14—C13—H13	118.9
C2—C3—H3	119.8	C12—C13—H13	118.9
C4—C3—H3	119.8	C13—C14—C15	119.8 (2)
C5—C4—C3	120.8 (2)	C13—C14—H14	120.1
C5—C4—H4	119.6	C15—C14—H14	120.1
C3—C4—H4	119.6	C14—C15—C16	123.5 (2)
C4—C5—C6	120.1 (2)	C14—C15—C19	119.3 (2)
C4—C5—H5	119.9	C16—C15—C19	117.19 (18)
C6—C5—H5	119.9	C17—C16—C15	119.7 (2)
C7—C6—C5	122.86 (19)	C17—C16—H16	120.2
C7—C6—C1	117.81 (18)	C15—C16—H16	120.2
C5—C6—C1	119.30 (18)	C16—C17—C18	119.0 (2)
C8—C7—C6	119.55 (19)	C16—C17—H17	120.5
C8—C7—H7	120.2	C18—C17—H17	120.5
C6—C7—H7	120.2	N3—C18—C17	124.4 (2)
C7—C8—C9	118.52 (19)	N3—C18—H18	117.8
C7—C8—H8	120.7	C17—C18—H18	117.8
C9—C8—H8	120.7	N3—C19—C11	117.95 (18)
N1—C9—C8	124.35 (19)	N3—C19—C15	122.76 (19)
N1—C9—C10	117.73 (18)	C11—C19—C15	119.28 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.88	2.27	2.693 (2)	109
N2—H2A···N3	0.88	2.27	2.684 (2)	109
C12—H12···O1	0.95	2.25	2.867 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1	0.88	2.27	2.693 (2)	109
N2—H2A⋯N3	0.88	2.27	2.684 (2)	109
C12—H12⋯O1	0.95	2.25	2.867 (2)	122