N'-[(E)-Benzyl-idene]-1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazide.

In the title compound, C(19)H(18)N(4)O(2), the 1,8-naphthyridine ring system is essentially planar [r.m.s. deviation = 0.011 (3) Å]. The dihedral angle between the naphthyridine ring system and the phenyl ring is 28.95 (7)°. The carbohydrazide H atom is involved in an intra-molecular N-H⋯O hydrogen bond, forming a six-membered hydrogen-bonded ring. In the crystal, the mol-ecules arrange themselves into centrosymmetric dimers by means of inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the synthesis of heterocyclic compounds, see: Chen et al. (2001 ▶); Zia-ur-Rehman et al. (2006 ▶, 2009 ▶). For their biological activity, see: Ferrarini et al. (2000 ▶); Hoock et al. (1999 ▶); Nakatani et al. (2001 ▶); Roma et al. (2000 ▶). For related structures, see: Catalano et al. (2000 ▶); Deeba et al. (2009 ▶).

Experimental

Crystal data

C19H18N4O2

M = 334.37

Triclinic,

a = 7.1642 (1) Å

b = 8.8383 (1) Å

c = 14.4560 (2) Å

α = 82.624 (6)°

β = 85.454 (7)°

γ = 68.594 (5)°

V = 844.63 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.983, T max = 0.991

18153 measured reflections

3446 independent reflections

2105 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.175

S = 1.03

3446 reflections

236 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048739/is2485sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048739/is2485Isup2.hkl

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

C19H18N4O2	Z = 2
Mr = 334.37	F(000) = 352
Triclinic, P1	Dx = 1.315 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1642 (1) Å	Cell parameters from 18153 reflections
b = 8.8383 (1) Å	θ = 2.5–26.4°
c = 14.4560 (2) Å	µ = 0.09 mm−1
α = 82.624 (6)°	T = 293 K
β = 85.454 (7)°	Needles, yellow
γ = 68.594 (5)°	0.20 × 0.10 × 0.10 mm
V = 844.63 (4) Å3

Rigaku R-AXIS RAPID-S diffractometer	3446 independent reflections
Radiation source: fine-focus sealed tube	2105 reflections with I > 2σ(I)
graphite	Rint = 0.066
ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −8→8
Tmin = 0.983, Tmax = 0.991	k = −11→11
18153 measured reflections	l = −18→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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0691P)2 + 0.1621P] where P = (Fo2 + 2Fc2)/3
3446 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	−0.1188 (4)	0.2780 (3)	0.28444 (16)	0.0632 (7)
H1C	−0.1027	0.1871	0.3312	0.095*
H1A	−0.2588	0.3349	0.2734	0.095*
H1B	−0.0637	0.3511	0.3056	0.095*
C8	0.3626 (5)	−0.3046 (4)	0.26006 (19)	0.0813 (9)
H8A	0.4932	−0.3472	0.2304	0.122*
H8C	0.3494	−0.3818	0.3109	0.122*
H8B	0.3459	−0.2034	0.2834	0.122*
H13	0.603 (4)	−0.009 (3)	−0.3488 (17)	0.072 (8)*
H1N	0.454 (4)	−0.035 (3)	−0.2036 (17)	0.065 (8)*
C5	0.1821 (3)	0.1032 (3)	0.03208 (15)	0.0469 (5)
O1	0.3049 (3)	0.1303 (2)	−0.12329 (11)	0.0627 (5)
N4	0.0597 (3)	0.0569 (2)	0.19056 (12)	0.0476 (5)
N3	0.2269 (3)	−0.1657 (2)	0.10789 (12)	0.0466 (5)
N1	0.4915 (3)	−0.1421 (3)	−0.20600 (13)	0.0546 (5)
C10	0.3530 (3)	−0.1374 (3)	−0.04983 (14)	0.0468 (5)
C9	0.3224 (3)	−0.2282 (3)	0.03032 (15)	0.0477 (5)
H9	0.3716	−0.3413	0.0308	0.057*
N2	0.5729 (3)	−0.2165 (3)	−0.28556 (13)	0.0574 (5)
C11	0.2838 (3)	0.0374 (3)	−0.05407 (15)	0.0480 (5)
C6	0.1544 (3)	0.0025 (3)	0.11057 (14)	0.0444 (5)
O2	0.5063 (3)	−0.3819 (2)	−0.12262 (11)	0.0682 (5)
C2	−0.0111 (3)	0.2171 (3)	0.19557 (16)	0.0510 (6)
C3	0.0108 (4)	0.3277 (3)	0.12111 (17)	0.0631 (7)
H3	−0.0395	0.4393	0.1266	0.076*
C13	0.6167 (4)	−0.1254 (4)	−0.35312 (17)	0.0580 (6)
C7	0.2050 (4)	−0.2758 (3)	0.19052 (15)	0.0564 (7)
H7B	0.2152	−0.3795	0.1709	0.068*
H7A	0.0733	−0.2281	0.2199	0.068*
C14	0.6940 (4)	−0.1896 (3)	−0.44275 (15)	0.0549 (6)
C4	0.1069 (4)	0.2702 (3)	0.04011 (17)	0.0594 (7)
H4	0.1221	0.3431	−0.0097	0.071*
C12	0.4574 (4)	−0.2336 (3)	−0.12865 (15)	0.0522 (6)
C15	0.7825 (4)	−0.1063 (3)	−0.50867 (17)	0.0681 (7)
H15	0.7952	−0.0104	−0.4953	0.082*
C19	0.6743 (5)	−0.3296 (4)	−0.46494 (18)	0.0778 (9)
H19	0.6135	−0.3863	−0.4219	0.093*
C17	0.8318 (5)	−0.3036 (4)	−0.6144 (2)	0.0901 (10)
H17	0.8780	−0.3421	−0.6720	0.108*
C16	0.8518 (5)	−0.1637 (4)	−0.59383 (19)	0.0807 (9)
H16	0.9123	−0.1073	−0.6373	0.097*
C18	0.7436 (6)	−0.3872 (4)	−0.5502 (2)	0.0992 (12)
H18	0.7305	−0.4826	−0.5640	0.119*

	U11	U22	U33	U12	U13	U23
C1	0.0648 (16)	0.0627 (16)	0.0549 (15)	−0.0110 (13)	0.0065 (12)	−0.0216 (12)
C8	0.108 (2)	0.0676 (18)	0.0590 (16)	−0.0244 (17)	−0.0082 (16)	0.0081 (14)
C5	0.0490 (13)	0.0456 (12)	0.0439 (12)	−0.0144 (10)	0.0011 (10)	−0.0061 (10)
O1	0.0816 (13)	0.0578 (10)	0.0443 (9)	−0.0239 (9)	0.0122 (8)	−0.0018 (8)
N4	0.0495 (11)	0.0484 (11)	0.0412 (10)	−0.0126 (9)	0.0058 (8)	−0.0109 (8)
N3	0.0524 (11)	0.0450 (10)	0.0398 (10)	−0.0149 (9)	0.0093 (8)	−0.0096 (8)
N1	0.0641 (13)	0.0592 (13)	0.0389 (11)	−0.0206 (11)	0.0121 (9)	−0.0124 (9)
C10	0.0482 (13)	0.0518 (13)	0.0381 (11)	−0.0155 (10)	0.0046 (10)	−0.0082 (10)
C9	0.0492 (13)	0.0460 (12)	0.0448 (12)	−0.0133 (10)	0.0070 (10)	−0.0111 (10)
N2	0.0586 (13)	0.0661 (13)	0.0432 (11)	−0.0171 (10)	0.0096 (9)	−0.0136 (9)
C11	0.0504 (13)	0.0540 (13)	0.0392 (11)	−0.0192 (11)	0.0038 (10)	−0.0063 (10)
C6	0.0421 (12)	0.0461 (12)	0.0408 (11)	−0.0112 (10)	0.0033 (9)	−0.0070 (9)
O2	0.0869 (13)	0.0542 (11)	0.0533 (10)	−0.0148 (9)	0.0182 (9)	−0.0144 (8)
C2	0.0487 (13)	0.0503 (13)	0.0493 (13)	−0.0099 (11)	0.0003 (10)	−0.0133 (11)
C3	0.0777 (18)	0.0438 (13)	0.0589 (15)	−0.0108 (13)	0.0029 (13)	−0.0105 (11)
C13	0.0620 (16)	0.0665 (17)	0.0463 (14)	−0.0239 (13)	0.0064 (11)	−0.0119 (12)
C7	0.0746 (17)	0.0453 (13)	0.0436 (12)	−0.0187 (12)	0.0179 (12)	−0.0054 (10)
C14	0.0554 (15)	0.0638 (15)	0.0403 (12)	−0.0161 (12)	0.0055 (10)	−0.0076 (11)
C4	0.0732 (17)	0.0480 (14)	0.0499 (14)	−0.0157 (12)	0.0022 (12)	−0.0011 (11)
C12	0.0525 (14)	0.0578 (15)	0.0435 (13)	−0.0162 (12)	0.0070 (10)	−0.0111 (11)
C15	0.0797 (19)	0.0685 (17)	0.0563 (15)	−0.0290 (15)	0.0143 (13)	−0.0099 (13)
C19	0.110 (2)	0.0807 (19)	0.0517 (15)	−0.0485 (18)	0.0251 (15)	−0.0146 (14)
C17	0.125 (3)	0.095 (2)	0.0570 (17)	−0.048 (2)	0.0380 (17)	−0.0298 (16)
C16	0.095 (2)	0.089 (2)	0.0568 (16)	−0.0363 (18)	0.0282 (15)	−0.0125 (15)
C18	0.154 (3)	0.095 (2)	0.0663 (19)	−0.066 (2)	0.038 (2)	−0.0343 (17)

C1—C2	1.501 (3)	C9—H9	0.9300
C1—H1C	0.9600	N2—C13	1.279 (3)
C1—H1A	0.9600	O2—C12	1.220 (3)
C1—H1B	0.9600	C2—C3	1.397 (3)
C8—C7	1.501 (4)	C3—C4	1.369 (3)
C8—H8A	0.9600	C3—H3	0.9300
C8—H8C	0.9600	C13—C14	1.467 (3)
C8—H8B	0.9600	C13—H13	1.01 (3)
C5—C4	1.391 (3)	C7—H7B	0.9700
C5—C6	1.398 (3)	C7—H7A	0.9700
C5—C11	1.467 (3)	C14—C19	1.375 (4)
O1—C11	1.246 (3)	C14—C15	1.384 (3)
N4—C2	1.328 (3)	C4—H4	0.9300
N4—C6	1.345 (3)	C15—C16	1.378 (3)
N3—C9	1.339 (3)	C15—H15	0.9300
N3—C6	1.388 (3)	C19—C18	1.379 (4)
N3—C7	1.477 (3)	C19—H19	0.9300
N1—C12	1.354 (3)	C17—C16	1.367 (4)
N1—N2	1.379 (3)	C17—C18	1.370 (4)
N1—H1N	0.89 (3)	C17—H17	0.9300
C10—C9	1.373 (3)	C16—H16	0.9300
C10—C11	1.435 (3)	C18—H18	0.9300
C10—C12	1.494 (3)
C2—C1—H1C	109.5	C3—C2—C1	120.2 (2)
C2—C1—H1A	109.5	C4—C3—C2	119.4 (2)
H1C—C1—H1A	109.5	C4—C3—H3	120.3
C2—C1—H1B	109.5	C2—C3—H3	120.3
H1C—C1—H1B	109.5	N2—C13—C14	120.2 (2)
H1A—C1—H1B	109.5	N2—C13—H13	123.6 (14)
C7—C8—H8A	109.5	C14—C13—H13	116.3 (14)
C7—C8—H8C	109.5	N3—C7—C8	111.6 (2)
H8A—C8—H8C	109.5	N3—C7—H7B	109.3
C7—C8—H8B	109.5	C8—C7—H7B	109.3
H8A—C8—H8B	109.5	N3—C7—H7A	109.3
H8C—C8—H8B	109.5	C8—C7—H7A	109.3
C4—C5—C6	116.1 (2)	H7B—C7—H7A	108.0
C4—C5—C11	121.7 (2)	C19—C14—C15	118.3 (2)
C6—C5—C11	122.2 (2)	C19—C14—C13	121.3 (2)
C2—N4—C6	117.81 (19)	C15—C14—C13	120.3 (2)
C9—N3—C6	119.42 (18)	C3—C4—C5	120.2 (2)
C9—N3—C7	119.91 (18)	C3—C4—H4	119.9
C6—N3—C7	120.65 (17)	C5—C4—H4	119.9
C12—N1—N2	119.2 (2)	O2—C12—N1	123.7 (2)
C12—N1—H1N	117.7 (16)	O2—C12—C10	122.0 (2)
N2—N1—H1N	123.0 (16)	N1—C12—C10	114.2 (2)
C9—C10—C11	120.18 (19)	C16—C15—C14	120.8 (3)
C9—C10—C12	115.2 (2)	C16—C15—H15	119.6
C11—C10—C12	124.6 (2)	C14—C15—H15	119.6
N3—C9—C10	124.7 (2)	C14—C19—C18	120.9 (3)
N3—C9—H9	117.7	C14—C19—H19	119.5
C10—C9—H9	117.7	C18—C19—H19	119.5
C13—N2—N1	115.6 (2)	C16—C17—C18	120.0 (3)
O1—C11—C10	125.0 (2)	C16—C17—H17	120.0
O1—C11—C5	120.8 (2)	C18—C17—H17	120.0
C10—C11—C5	114.23 (19)	C17—C16—C15	120.0 (3)
N4—C6—N3	116.26 (19)	C17—C16—H16	120.0
N4—C6—C5	124.4 (2)	C15—C16—H16	120.0
N3—C6—C5	119.32 (18)	C17—C18—C19	120.0 (3)
N4—C2—C3	122.0 (2)	C17—C18—H18	120.0
N4—C2—C1	117.8 (2)	C19—C18—H18	120.0
C6—N3—C9—C10	−1.1 (3)	N4—C2—C3—C4	0.3 (4)
C7—N3—C9—C10	−179.3 (2)	C1—C2—C3—C4	−179.1 (2)
C11—C10—C9—N3	1.2 (4)	N1—N2—C13—C14	−176.7 (2)
C12—C10—C9—N3	−178.0 (2)	C9—N3—C7—C8	97.7 (3)
C12—N1—N2—C13	−174.3 (2)	C6—N3—C7—C8	−80.4 (3)
C9—C10—C11—O1	179.8 (2)	N2—C13—C14—C19	16.6 (4)
C12—C10—C11—O1	−1.2 (4)	N2—C13—C14—C15	−165.8 (2)
C9—C10—C11—C5	−0.3 (3)	C2—C3—C4—C5	0.0 (4)
C12—C10—C11—C5	178.8 (2)	C6—C5—C4—C3	−0.5 (4)
C4—C5—C11—O1	−0.4 (4)	C11—C5—C4—C3	179.3 (2)
C6—C5—C11—O1	179.4 (2)	N2—N1—C12—O2	4.9 (4)
C4—C5—C11—C10	179.6 (2)	N2—N1—C12—C10	−174.99 (19)
C6—C5—C11—C10	−0.6 (3)	C9—C10—C12—O2	2.0 (4)
C2—N4—C6—N3	179.8 (2)	C11—C10—C12—O2	−177.1 (2)
C2—N4—C6—C5	−0.5 (3)	C9—C10—C12—N1	−178.1 (2)
C9—N3—C6—N4	179.85 (19)	C11—C10—C12—N1	2.8 (3)
C7—N3—C6—N4	−2.0 (3)	C19—C14—C15—C16	−1.0 (4)
C9—N3—C6—C5	0.1 (3)	C13—C14—C15—C16	−178.7 (3)
C7—N3—C6—C5	178.3 (2)	C15—C14—C19—C18	0.9 (5)
C4—C5—C6—N4	0.8 (3)	C13—C14—C19—C18	178.6 (3)
C11—C5—C6—N4	−179.0 (2)	C18—C17—C16—C15	−0.3 (5)
C4—C5—C6—N3	−179.5 (2)	C14—C15—C16—C17	0.7 (5)
C11—C5—C6—N3	0.7 (3)	C16—C17—C18—C19	0.3 (6)
C6—N4—C2—C3	−0.1 (3)	C14—C19—C18—C17	−0.6 (6)
C6—N4—C2—C1	179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.89 (3)	1.93 (2)	2.674 (3)	140 (2)
C7—H7B···O2i	0.97	2.45	3.204 (3)	134
C9—H9···O2i	0.93	2.51	3.340 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.89 (3)	1.93 (2)	2.674 (3)	140 (2)
C7—H7B⋯O2i	0.97	2.45	3.204 (3)	134
C9—H9⋯O2i	0.93	2.51	3.340 (3)	149

Symmetry code: (i) .