(E)-1-Ethyl-4-oxo-N'-(4-pyridylmethyl-ene)-1,4-dihydroquinoline-3-carbo-hydrazide.

In the title compound, C(18)H(16)N(4)O(2), the plane defined by the ethyl C atoms and the attached N atom is inclined to the adjacent pyridine ring at an angle of 67.87 (16)°. The dihedral angle between the two heterocyclic rings is 3.33 (16)°. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond and the crystal structure by inter-molecular C-H⋯O hydrogen bonds, forming a one-dimensional structure.

Related literature

For the biological properties of oxoquinoline derivatives, see: Van Bambeke et al. (2005 ▶); Canuto et al. (2007 ▶); Lucero et al. (2006 ▶). For their potential use in the treatment of fungal and viral infections, see: Brideau et al. (2002 ▶); Souza et al. (2008 ▶) and in cancer chemotherapy, see: Chu et al. (1992 ▶). For acyl­hydrazones and their anti­leishmanial activity, see: Bernadino et al. (2006 ▶); Cunha et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H16N4O2

M = 320.35

Monoclinic,

a = 7.6460 (12) Å

b = 19.205 (2) Å

c = 10.7050 (9) Å

β = 99.722 (10)°

V = 1549.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.5 × 0.2 × 0.2 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

7914 measured reflections

2586 independent reflections

2001 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.102

S = 1.07

2586 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997 ▶); data reduction: HKL DENZO (Otwinowski & Minor 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903654X/wn2340sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903654X/wn2340Isup2.hkl

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

C18H16N4O2	F(000) = 672
Mr = 320.35	Dx = 1.373 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7914 reflections
a = 7.6460 (12) Å	θ = 5.2–25°
b = 19.205 (2) Å	µ = 0.09 mm−1
c = 10.7050 (9) Å	T = 293 K
β = 99.722 (10)°	Prism, yellow
V = 1549.4 (3) Å3	0.5 × 0.2 × 0.2 mm
Z = 4

Nonius KappaCCD diffractometer	2001 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 25.0°, θmin = 5.2°
Detector resolution: 9 pixels mm-1	h = −9→9
φ scans and ω scans winth κ offsets	k = −22→20
7914 measured reflections	l = −12→8
2586 independent reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0352P)2 + 0.5415P] where P = (Fo2 + 2Fc2)/3
2586 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.9168 (2)	0.11495 (9)	0.16391 (15)	0.0361 (4)
C2	0.8969 (2)	0.07582 (10)	0.05163 (16)	0.0455 (4)
H2	0.8539	0.0305	0.0514	0.055*
C3	0.9396 (3)	0.10304 (10)	−0.05772 (17)	0.0516 (5)
H3	0.9240	0.0768	−0.1318	0.062*
C4	1.0065 (3)	0.17027 (11)	−0.05650 (17)	0.0521 (5)
H4	1.0374	0.1886	−0.1302	0.063*
C5	1.0280 (2)	0.21026 (10)	0.05098 (16)	0.0471 (4)
H5	1.0740	0.2550	0.0500	0.056*
C6	0.9804 (2)	0.18344 (9)	0.16269 (15)	0.0374 (4)
C7	0.8708 (2)	0.08354 (9)	0.27920 (15)	0.0371 (4)
C8	0.8931 (2)	0.12883 (8)	0.38879 (15)	0.0365 (4)
C9	0.9529 (2)	0.19544 (9)	0.37882 (15)	0.0401 (4)
H9	0.9638	0.2235	0.4505	0.048*
C10	1.0520 (3)	0.29759 (10)	0.27524 (18)	0.0538 (5)
H10A	1.1500	0.3026	0.2291	0.065*
H10B	1.0931	0.3118	0.3622	0.065*
C11	0.9018 (3)	0.34469 (11)	0.2170 (2)	0.0750 (7)
H11A	0.9448	0.3915	0.2143	0.113*
H11B	0.8090	0.3432	0.2671	0.113*
H11C	0.8563	0.3293	0.1324	0.113*
C12	0.8472 (2)	0.10900 (9)	0.51400 (16)	0.0416 (4)
C13	0.6773 (2)	−0.04576 (9)	0.61567 (16)	0.0429 (4)
H13	0.6722	−0.0691	0.5391	0.051*
C14	0.6223 (2)	−0.08221 (9)	0.72279 (15)	0.0388 (4)
C15	0.5717 (2)	−0.15131 (9)	0.71190 (17)	0.0494 (5)
H15	0.5690	−0.1747	0.6356	0.059*
C16	0.5249 (3)	−0.18542 (10)	0.81527 (19)	0.0544 (5)
H16	0.4916	−0.2319	0.8057	0.065*
C17	0.5729 (3)	−0.08884 (11)	0.93622 (18)	0.0551 (5)
H17	0.5739	−0.0667	1.0136	0.066*
C18	0.6209 (2)	−0.05045 (10)	0.83932 (17)	0.0479 (4)
H18	0.6521	−0.0038	0.8514	0.057*
N1	0.99728 (18)	0.22334 (7)	0.27329 (12)	0.0402 (4)
N2	0.73182 (18)	0.01676 (7)	0.62429 (13)	0.0419 (4)
N3	0.7828 (2)	0.04327 (8)	0.51697 (14)	0.0445 (4)
N4	0.5248 (2)	−0.15582 (9)	0.92715 (15)	0.0541 (4)
O1	0.81667 (17)	0.02200 (6)	0.27864 (11)	0.0522 (3)
O2	0.8639 (2)	0.14902 (7)	0.60464 (12)	0.0636 (4)
H3N	0.776 (2)	0.0178 (10)	0.4436 (19)	0.057 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0335 (8)	0.0403 (10)	0.0342 (9)	0.0054 (7)	0.0048 (7)	−0.0024 (7)
C2	0.0512 (10)	0.0443 (10)	0.0408 (10)	0.0051 (8)	0.0074 (8)	−0.0066 (8)
C3	0.0632 (12)	0.0569 (12)	0.0346 (10)	0.0102 (10)	0.0078 (8)	−0.0070 (8)
C4	0.0603 (12)	0.0623 (13)	0.0366 (10)	0.0074 (10)	0.0163 (8)	0.0047 (9)
C5	0.0523 (11)	0.0506 (11)	0.0409 (10)	0.0003 (9)	0.0151 (8)	0.0035 (8)
C6	0.0360 (9)	0.0428 (10)	0.0343 (9)	0.0027 (7)	0.0088 (7)	−0.0018 (7)
C7	0.0364 (9)	0.0365 (9)	0.0388 (9)	0.0030 (7)	0.0075 (7)	−0.0011 (7)
C8	0.0391 (9)	0.0362 (9)	0.0354 (9)	0.0013 (7)	0.0101 (7)	−0.0018 (7)
C9	0.0456 (10)	0.0427 (10)	0.0342 (9)	−0.0017 (8)	0.0132 (7)	−0.0055 (7)
C10	0.0727 (13)	0.0478 (11)	0.0452 (10)	−0.0231 (10)	0.0227 (9)	−0.0063 (9)
C11	0.114 (2)	0.0441 (12)	0.0719 (15)	−0.0014 (13)	0.0312 (14)	0.0043 (11)
C12	0.0491 (10)	0.0379 (10)	0.0403 (10)	0.0021 (8)	0.0144 (8)	−0.0024 (8)
C13	0.0520 (10)	0.0398 (10)	0.0368 (9)	−0.0028 (8)	0.0071 (8)	−0.0011 (7)
C14	0.0380 (9)	0.0378 (9)	0.0394 (9)	0.0020 (7)	0.0029 (7)	0.0047 (7)
C15	0.0611 (12)	0.0424 (10)	0.0440 (10)	−0.0037 (9)	0.0066 (9)	0.0000 (8)
C16	0.0643 (13)	0.0409 (11)	0.0573 (12)	−0.0057 (9)	0.0084 (10)	0.0082 (9)
C17	0.0720 (13)	0.0519 (12)	0.0446 (11)	0.0025 (10)	0.0191 (9)	0.0019 (9)
C18	0.0584 (11)	0.0402 (10)	0.0457 (10)	−0.0006 (8)	0.0110 (8)	−0.0003 (8)
N1	0.0474 (8)	0.0392 (8)	0.0361 (8)	−0.0068 (6)	0.0128 (6)	−0.0033 (6)
N2	0.0500 (9)	0.0395 (9)	0.0381 (8)	−0.0008 (7)	0.0125 (6)	0.0029 (6)
N3	0.0613 (10)	0.0397 (9)	0.0353 (8)	−0.0056 (7)	0.0158 (7)	0.0001 (7)
N4	0.0598 (10)	0.0525 (10)	0.0521 (10)	0.0032 (8)	0.0149 (8)	0.0113 (8)
O1	0.0732 (9)	0.0387 (7)	0.0464 (7)	−0.0095 (6)	0.0147 (6)	−0.0056 (5)
O2	0.1082 (11)	0.0441 (8)	0.0471 (8)	−0.0128 (7)	0.0379 (7)	−0.0102 (6)

C1—C6	1.403 (2)	C10—H10B	0.9700
C1—C2	1.404 (2)	C11—H11A	0.9600
C1—C7	1.469 (2)	C11—H11B	0.9600
C2—C3	1.371 (2)	C11—H11C	0.9600
C2—H2	0.9300	C12—O2	1.227 (2)
C3—C4	1.388 (3)	C12—N3	1.357 (2)
C3—H3	0.9300	C13—N2	1.269 (2)
C4—C5	1.370 (2)	C13—C14	1.465 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.405 (2)	C14—C15	1.382 (2)
C5—H5	0.9300	C14—C18	1.390 (2)
C6—N1	1.398 (2)	C15—C16	1.384 (3)
C7—O1	1.2518 (19)	C15—H15	0.9300
C7—C8	1.447 (2)	C16—N4	1.326 (2)
C8—C9	1.369 (2)	C16—H16	0.9300
C8—C12	1.491 (2)	C17—N4	1.337 (2)
C9—N1	1.344 (2)	C17—C18	1.372 (3)
C9—H9	0.9300	C17—H17	0.9300
C10—N1	1.485 (2)	C18—H18	0.9300
C10—C11	1.511 (3)	N2—N3	1.3719 (19)
C10—H10A	0.9700	N3—H3N	0.92 (2)
C6—C1—C2	118.79 (15)	C10—C11—H11B	109.5
C6—C1—C7	121.70 (14)	H11A—C11—H11B	109.5
C2—C1—C7	119.52 (15)	C10—C11—H11C	109.5
C3—C2—C1	121.32 (17)	H11A—C11—H11C	109.5
C3—C2—H2	119.3	H11B—C11—H11C	109.5
C1—C2—H2	119.3	O2—C12—N3	123.61 (16)
C2—C3—C4	119.16 (17)	O2—C12—C8	122.81 (15)
C2—C3—H3	120.4	N3—C12—C8	113.58 (14)
C4—C3—H3	120.4	N2—C13—C14	121.97 (15)
C5—C4—C3	121.40 (17)	N2—C13—H13	119.0
C5—C4—H4	119.3	C14—C13—H13	119.0
C3—C4—H4	119.3	C15—C14—C18	116.92 (16)
C4—C5—C6	119.85 (17)	C15—C14—C13	120.43 (16)
C4—C5—H5	120.1	C18—C14—C13	122.65 (16)
C6—C5—H5	120.1	C14—C15—C16	119.58 (17)
N1—C6—C1	119.25 (14)	C14—C15—H15	120.2
N1—C6—C5	121.31 (16)	C16—C15—H15	120.2
C1—C6—C5	119.44 (15)	N4—C16—C15	123.99 (18)
O1—C7—C8	124.40 (15)	N4—C16—H16	118.0
O1—C7—C1	120.64 (14)	C15—C16—H16	118.0
C8—C7—C1	114.96 (14)	N4—C17—C18	124.58 (18)
C9—C8—C7	119.59 (14)	N4—C17—H17	117.7
C9—C8—C12	116.19 (14)	C18—C17—H17	117.7
C7—C8—C12	124.17 (15)	C17—C18—C14	119.08 (18)
N1—C9—C8	124.96 (15)	C17—C18—H18	120.5
N1—C9—H9	117.5	C14—C18—H18	120.5
C8—C9—H9	117.5	C9—N1—C6	119.53 (14)
N1—C10—C11	112.13 (16)	C9—N1—C10	118.75 (14)
N1—C10—H10A	109.2	C6—N1—C10	121.59 (13)
C11—C10—H10A	109.2	C13—N2—N3	115.25 (14)
N1—C10—H10B	109.2	C12—N3—N2	121.35 (15)
C11—C10—H10B	109.2	C12—N3—H3N	116.4 (12)
H10A—C10—H10B	107.9	N2—N3—H3N	122.2 (12)
C10—C11—H11A	109.5	C16—N4—C17	115.84 (16)
C6—C1—C2—C3	0.6 (2)	C6—C1—C2—H2	−179.4
C7—C1—C2—C3	−179.53 (16)	C7—C1—C2—H2	0.5
C1—C2—C3—C4	1.0 (3)	C1—C2—C3—H3	−179.0
C2—C3—C4—C5	−1.1 (3)	H2—C2—C3—H3	1.0
C3—C4—C5—C6	−0.6 (3)	H2—C2—C3—C4	−179.0
C2—C1—C6—N1	178.70 (14)	C2—C3—C4—H4	178.9
C7—C1—C6—N1	−1.2 (2)	H3—C3—C4—H4	−1.1
C2—C1—C6—C5	−2.2 (2)	H3—C3—C4—C5	178.9
C7—C1—C6—C5	177.95 (14)	C3—C4—C5—H5	179.4
C4—C5—C6—N1	−178.71 (16)	H4—C4—C5—H5	−0.6
C4—C5—C6—C1	2.2 (3)	H4—C4—C5—C6	179.4
C6—C1—C7—O1	−178.98 (15)	H5—C5—C6—C1	−177.8
C2—C1—C7—O1	1.1 (2)	H5—C5—C6—N1	1.3
C6—C1—C7—C8	1.0 (2)	C7—C8—C9—H9	178.8
C2—C1—C7—C8	−178.88 (14)	C12—C8—C9—H9	1.4
O1—C7—C8—C9	−179.87 (16)	H9—C9—N1—C10	−2.9
C1—C7—C8—C9	0.1 (2)	H9—C9—N1—C6	−178.9
O1—C7—C8—C12	−2.7 (3)	H10A—C10—C11—H11A	−54.6
C1—C7—C8—C12	177.27 (14)	H10A—C10—C11—H11B	−174.6
C7—C8—C9—N1	−1.2 (3)	H10A—C10—C11—H11C	65.4
C12—C8—C9—N1	−178.55 (15)	H10B—C10—C11—H11A	63.1
C9—C8—C12—O2	−1.1 (3)	H10B—C10—C11—H11B	−56.9
C7—C8—C12—O2	−178.36 (17)	H10B—C10—C11—H11C	−176.9
C9—C8—C12—N3	177.80 (15)	N1—C10—C11—H11A	−175.7
C7—C8—C12—N3	0.6 (2)	N1—C10—C11—H11B	64.3
N2—C13—C14—C15	−176.91 (16)	N1—C10—C11—H11C	−55.7
N2—C13—C14—C18	1.9 (3)	H10A—C10—N1—C6	−43.9
C18—C14—C15—C16	−0.8 (3)	H10A—C10—N1—C9	140.2
C13—C14—C15—C16	178.15 (16)	H10B—C10—N1—C6	−161.6
C14—C15—C16—N4	0.2 (3)	H10B—C10—N1—C9	22.5
N4—C17—C18—C14	−0.6 (3)	C8—C12—N3—H3N	1.0 (13)
C15—C14—C18—C17	0.9 (3)	H13—C13—C14—C15	3.1
C13—C14—C18—C17	−177.93 (17)	H13—C13—C14—C18	−178.1
C8—C9—N1—C6	1.1 (2)	H13—C13—N2—N3	−1.5
C8—C9—N1—C10	177.08 (16)	C13—C14—C15—H15	−1.8
C1—C6—N1—C9	0.2 (2)	C18—C14—C15—H15	179.2
C5—C6—N1—C9	−178.95 (15)	C13—C14—C18—H18	2.1
C1—C6—N1—C10	−175.74 (15)	C15—C14—C18—H18	−179.1
C5—C6—N1—C10	5.1 (2)	C14—C15—C16—H16	−179.8
C11—C10—N1—C9	−98.68 (19)	H15—C15—C16—H16	0.2
C11—C10—N1—C6	77.3 (2)	H15—C15—C16—N4	−179.8
C14—C13—N2—N3	178.47 (14)	H16—C16—N4—C17	−179.7
O2—C12—N3—N2	−0.3 (3)	H17—C17—C18—C14	179.4
C8—C12—N3—N2	−179.21 (14)	H17—C17—C18—H18	−0.6
C13—N2—N3—C12	−178.62 (16)	N4—C17—C18—H18	179.4
C15—C16—N4—C17	0.3 (3)	H17—C17—N4—C16	180.0
C18—C17—N4—C16	0.0 (3)	C13—N2—N3—H3N	1.2 (14)
C6—C1—C2—H2	−179.43 (1)	O2—C12—N3—H3N	179.9 (13)
C7—C1—C2—H2	0.46 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1	0.92 (2)	1.85 (2)	2.639 (2)	143.1 (17)
C10—H10A···O2i	0.97	2.46	3.398 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1	0.92 (2)	1.85 (2)	2.639 (2)	143.1 (17)
C10—H10A⋯O2i	0.97	2.46	3.398 (2)	163

Symmetry code: (i) .