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

In the crystal structure of the title compound, C(19)H(18)N(4)O(3), the fused-ring system is essentially planar [maximum deviation is 0.031 (2) Å] while the dihedral angle between the ring system and the benzene ring is 12.64 (6)°.The carbohydrazide H atom is involved in an intra-molecular N-H⋯O hydrogen bond, forming a six-membered hydrogen-bonded ring. The mol-ecules arrange themselves into centrosymmetric dimers by means of inter-molecular O-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 ▶); Gavrilova & Bosnich (2004 ▶); Goswami & Mukherjee (1997 ▶); Hoock et al. (1999 ▶); Mintert & Sheldrick (1995 ▶); Nakatani et al. (2000 ▶); Nakataniz et al. (2001 ▶); Roma et al. (2000 ▶). For similar mol­ecules, see: Catalano et al. (2000 ▶).

Experimental

Crystal data

C19H18N4O3

M = 350.37

Monoclinic,

a = 7.6437 (2) Å

b = 13.3290 (2) Å

c = 17.2212 (4) Å

β = 98.1745 (14)°

V = 1736.72 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.2 × 0.14 × 0.1 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.990, T max = 0.991

35553 measured reflections

3583 independent reflections

2597 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.151

S = 1.04

3583 reflections

244 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.16 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009167/ng2560sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009167/ng2560Isup2.hkl

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

C19H18N4O3	F(000) = 736
Mr = 350.37	Dx = 1.34 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3643 reflections
a = 7.6437 (2) Å	θ = 2.4–26.4°
b = 13.3290 (2) Å	µ = 0.09 mm−1
c = 17.2212 (4) Å	T = 293 K
β = 98.1745 (14)°	Prism, light yellow
V = 1736.72 (7) Å3	0.2 × 0.14 × 0.1 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	3583 independent reflections
graphite	2597 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm-1	Rint = 0.064
ω scans	θmax = 26.7°, θmin = 2.4°
Absorption correction: multi-scan (Blessing, 1995)	h = −8→9
Tmin = 0.990, Tmax = 0.991	k = −16→16
35553 measured reflections	l = −21→21

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0654P)2 + 0.3979P] where P = (Fo2 + 2Fc2)/3
3583 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 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
O1	0.2080 (2)	0.01852 (11)	0.57270 (8)	0.0654 (4)
O3	−0.1795 (2)	−0.65000 (11)	0.71180 (9)	0.0686 (4)
H3O	−0.1729	−0.6919	0.6775	0.103*
N1	0.4591 (2)	0.22498 (12)	0.39012 (10)	0.0556 (4)
N3	0.1243 (2)	−0.16773 (13)	0.52592 (10)	0.0554 (4)
N4	0.0658 (2)	−0.26173 (12)	0.54348 (10)	0.0554 (4)
O2	0.1598 (2)	−0.20967 (11)	0.40138 (9)	0.0750 (5)
N2	0.3819 (2)	0.05987 (12)	0.36073 (9)	0.0532 (4)
C17	−0.1341 (3)	−0.55811 (15)	0.68611 (11)	0.0524 (5)
C14	−0.0321 (3)	−0.36963 (14)	0.63803 (11)	0.0517 (5)
C11	0.2538 (3)	0.03007 (14)	0.50649 (11)	0.0505 (5)
C10	0.2423 (3)	−0.04590 (14)	0.44689 (11)	0.0493 (5)
C16	−0.1130 (3)	−0.54200 (15)	0.60834 (11)	0.0567 (5)
H16	−0.1315	−0.594	0.5721	0.068*
C9	0.3081 (3)	−0.02682 (15)	0.37834 (12)	0.0544 (5)
H9	0.3009	−0.0779	0.3413	0.065*
C13	0.0289 (3)	−0.27273 (16)	0.61292 (12)	0.0561 (5)
C15	−0.0647 (3)	−0.44868 (15)	0.58534 (11)	0.0590 (5)
H15	−0.0533	−0.438	0.5329	0.071*
C6	0.3892 (3)	0.13908 (14)	0.41286 (11)	0.0494 (5)
C18	−0.1077 (3)	−0.48014 (16)	0.73924 (11)	0.0580 (5)
H18	−0.1243	−0.4903	0.7911	0.07*
C5	0.3272 (3)	0.12561 (14)	0.48473 (11)	0.0500 (5)
C2	0.4702 (3)	0.30211 (15)	0.43905 (13)	0.0586 (5)
C12	0.1715 (3)	−0.14835 (14)	0.45515 (12)	0.0539 (5)
C19	−0.0567 (3)	−0.38686 (15)	0.71523 (11)	0.0562 (5)
H19	−0.0385	−0.3348	0.7515	0.067*
C1	0.5445 (3)	0.39767 (17)	0.41103 (15)	0.0736 (7)
H1A	0.5764	0.3875	0.3597	0.11*
H1C	0.6474	0.4168	0.4466	0.11*
H1B	0.4573	0.4498	0.4089	0.11*
C4	0.3414 (3)	0.20843 (16)	0.53477 (13)	0.0648 (6)
H4	0.3023	0.2041	0.5834	0.078*
C3	0.4127 (4)	0.29585 (17)	0.51221 (13)	0.0716 (6)
H3	0.4229	0.3511	0.5456	0.086*
C7	0.4608 (3)	0.06988 (18)	0.28730 (12)	0.0679 (6)
H7A	0.4911	0.0038	0.2698	0.082*
H7B	0.5691	0.1086	0.2979	0.082*
C8	0.3387 (4)	0.1199 (3)	0.22344 (15)	0.1028 (10)
H8B	0.3956	0.1254	0.1774	0.154*
H8C	0.3093	0.1857	0.2403	0.154*
H8A	0.2328	0.0808	0.2116	0.154*
H13	0.045 (3)	−0.2191 (17)	0.6511 (13)	0.067 (6)*
H3N	0.131 (3)	−0.1174 (17)	0.5616 (13)	0.070 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0978 (11)	0.0566 (9)	0.0456 (8)	−0.0032 (8)	0.0238 (8)	0.0018 (6)
O3	0.1010 (12)	0.0523 (8)	0.0579 (9)	−0.0040 (8)	0.0296 (9)	0.0053 (7)
N1	0.0569 (10)	0.0537 (10)	0.0566 (10)	−0.0026 (8)	0.0098 (8)	0.0042 (8)
N3	0.0732 (11)	0.0448 (9)	0.0499 (10)	−0.0026 (8)	0.0139 (8)	0.0024 (8)
N4	0.0676 (11)	0.0446 (9)	0.0551 (10)	−0.0016 (8)	0.0125 (8)	0.0040 (7)
O2	0.1160 (14)	0.0533 (9)	0.0596 (9)	−0.0130 (8)	0.0259 (9)	−0.0086 (7)
N2	0.0632 (10)	0.0529 (9)	0.0466 (9)	−0.0036 (8)	0.0186 (7)	−0.0010 (7)
C17	0.0623 (12)	0.0483 (11)	0.0491 (11)	0.0007 (9)	0.0159 (9)	0.0051 (8)
C14	0.0608 (12)	0.0479 (10)	0.0481 (11)	−0.0006 (9)	0.0131 (9)	0.0019 (8)
C11	0.0581 (12)	0.0503 (11)	0.0436 (10)	0.0056 (9)	0.0093 (8)	0.0023 (8)
C10	0.0561 (11)	0.0473 (10)	0.0452 (10)	0.0009 (8)	0.0090 (8)	0.0025 (8)
C16	0.0767 (14)	0.0502 (11)	0.0454 (11)	−0.0023 (10)	0.0165 (10)	−0.0024 (8)
C9	0.0658 (13)	0.0496 (11)	0.0492 (11)	−0.0001 (9)	0.0132 (9)	−0.0043 (9)
C13	0.0698 (14)	0.0492 (11)	0.0507 (12)	0.0003 (10)	0.0130 (10)	−0.0005 (9)
C15	0.0837 (15)	0.0531 (12)	0.0438 (11)	−0.0039 (10)	0.0210 (10)	0.0011 (9)
C6	0.0526 (11)	0.0486 (10)	0.0472 (10)	0.0016 (8)	0.0082 (8)	0.0019 (8)
C18	0.0748 (14)	0.0598 (12)	0.0422 (10)	0.0000 (10)	0.0186 (9)	0.0041 (9)
C5	0.0579 (11)	0.0487 (11)	0.0439 (10)	0.0003 (9)	0.0084 (8)	0.0012 (8)
C2	0.0617 (13)	0.0507 (12)	0.0619 (13)	−0.0030 (9)	0.0038 (10)	0.0032 (10)
C12	0.0644 (13)	0.0476 (11)	0.0505 (11)	0.0016 (9)	0.0109 (9)	−0.0002 (9)
C19	0.0724 (13)	0.0526 (11)	0.0454 (10)	−0.0008 (10)	0.0143 (9)	−0.0043 (9)
C1	0.0827 (16)	0.0550 (13)	0.0837 (17)	−0.0096 (11)	0.0138 (13)	0.0068 (12)
C4	0.0901 (16)	0.0577 (13)	0.0476 (11)	−0.0027 (11)	0.0130 (11)	−0.0034 (9)
C3	0.1043 (19)	0.0523 (12)	0.0586 (13)	−0.0098 (12)	0.0126 (12)	−0.0079 (10)
C7	0.0866 (16)	0.0671 (14)	0.0573 (13)	−0.0084 (12)	0.0348 (12)	−0.0037 (10)
C8	0.111 (2)	0.144 (3)	0.0552 (15)	−0.011 (2)	0.0182 (15)	0.0164 (17)

O1—C11	1.249 (2)	C16—H16	0.93
O3—C17	1.364 (2)	C9—H9	0.93
O3—H3O	0.82	C13—H13	0.97 (2)
N1—C2	1.324 (3)	C15—H15	0.93
N1—C6	1.345 (2)	C6—C5	1.398 (3)
N3—C12	1.344 (3)	C18—C19	1.384 (3)
N3—N4	1.378 (2)	C18—H18	0.93
N3—H3N	0.91 (2)	C5—C4	1.395 (3)
N4—C13	1.275 (3)	C2—C3	1.394 (3)
O2—C12	1.229 (2)	C2—C1	1.502 (3)
N2—C9	1.340 (3)	C19—H19	0.93
N2—C6	1.382 (2)	C1—H1A	0.96
N2—C7	1.482 (2)	C1—H1C	0.96
C17—C18	1.380 (3)	C1—H1B	0.96
C17—C16	1.388 (3)	C4—C3	1.366 (3)
C14—C19	1.388 (3)	C4—H4	0.93
C14—C15	1.390 (3)	C3—H3	0.93
C14—C13	1.460 (3)	C7—C8	1.495 (4)
C11—C10	1.436 (3)	C7—H7A	0.97
C11—C5	1.462 (3)	C7—H7B	0.97
C10—C9	1.371 (3)	C8—H8B	0.96
C10—C12	1.483 (3)	C8—H8C	0.96
C16—C15	1.372 (3)	C8—H8A	0.96
C17—O3—H3O	109.5	C19—C18—H18	120
C2—N1—C6	117.86 (17)	C4—C5—C6	116.04 (18)
C12—N3—N4	120.71 (17)	C4—C5—C11	121.99 (18)
C12—N3—H3N	118.4 (15)	C6—C5—C11	121.97 (17)
N4—N3—H3N	120.9 (14)	N1—C2—C3	121.92 (19)
C13—N4—N3	115.59 (17)	N1—C2—C1	116.5 (2)
C9—N2—C6	119.42 (16)	C3—C2—C1	121.5 (2)
C9—N2—C7	120.42 (17)	O2—C12—N3	123.72 (19)
C6—N2—C7	120.13 (16)	O2—C12—C10	121.92 (18)
O3—C17—C18	118.75 (17)	N3—C12—C10	114.36 (17)
O3—C17—C16	121.44 (18)	C18—C19—C14	121.14 (19)
C18—C17—C16	119.80 (18)	C18—C19—H19	119.4
C19—C14—C15	117.65 (18)	C14—C19—H19	119.4
C19—C14—C13	121.51 (18)	C2—C1—H1A	109.5
C15—C14—C13	120.84 (18)	C2—C1—H1C	109.5
O1—C11—C10	124.68 (18)	H1A—C1—H1C	109.5
O1—C11—C5	120.61 (18)	C2—C1—H1B	109.5
C10—C11—C5	114.70 (16)	H1A—C1—H1B	109.5
C9—C10—C11	119.47 (18)	H1C—C1—H1B	109.5
C9—C10—C12	115.90 (17)	C3—C4—C5	119.9 (2)
C11—C10—C12	124.54 (17)	C3—C4—H4	120.1
C15—C16—C17	119.46 (18)	C5—C4—H4	120.1
C15—C16—H16	120.3	C4—C3—C2	119.8 (2)
C17—C16—H16	120.3	C4—C3—H3	120.1
N2—C9—C10	124.95 (18)	C2—C3—H3	120.1
N2—C9—H9	117.5	N2—C7—C8	112.4 (2)
C10—C9—H9	117.5	N2—C7—H7A	109.1
N4—C13—C14	120.13 (19)	C8—C7—H7A	109.1
N4—C13—H13	121.9 (13)	N2—C7—H7B	109.1
C14—C13—H13	117.9 (13)	C8—C7—H7B	109.1
C16—C15—C14	121.96 (18)	H7A—C7—H7B	107.9
C16—C15—H15	119	C7—C8—H8B	109.5
C14—C15—H15	119	C7—C8—H8C	109.5
N1—C6—N2	116.22 (17)	H8B—C8—H8C	109.5
N1—C6—C5	124.45 (18)	C7—C8—H8A	109.5
N2—C6—C5	119.32 (17)	H8B—C8—H8A	109.5
C17—C18—C19	119.94 (18)	H8C—C8—H8A	109.5
C17—C18—H18	120
C12—N3—N4—C13	178.2 (2)	N2—C6—C5—C4	179.03 (18)
O1—C11—C10—C9	−175.46 (19)	N1—C6—C5—C11	−179.47 (18)
C5—C11—C10—C9	3.8 (3)	N2—C6—C5—C11	−0.3 (3)
O1—C11—C10—C12	1.1 (3)	O1—C11—C5—C4	−3.1 (3)
C5—C11—C10—C12	−179.61 (18)	C10—C11—C5—C4	177.57 (19)
O3—C17—C16—C15	−179.0 (2)	O1—C11—C5—C6	176.24 (19)
C18—C17—C16—C15	0.5 (3)	C10—C11—C5—C6	−3.1 (3)
C6—N2—C9—C10	−2.4 (3)	C6—N1—C2—C3	0.3 (3)
C7—N2—C9—C10	175.4 (2)	C6—N1—C2—C1	−178.45 (19)
C11—C10—C9—N2	−1.3 (3)	N4—N3—C12—O2	3.0 (3)
C12—C10—C9—N2	−178.10 (19)	N4—N3—C12—C10	−176.28 (17)
N3—N4—C13—C14	−179.25 (18)	C9—C10—C12—O2	−5.6 (3)
C19—C14—C13—N4	173.6 (2)	C11—C10—C12—O2	177.8 (2)
C15—C14—C13—N4	−5.2 (3)	C9—C10—C12—N3	173.73 (18)
C17—C16—C15—C14	1.4 (3)	C11—C10—C12—N3	−2.9 (3)
C19—C14—C15—C16	−2.4 (3)	C17—C18—C19—C14	0.4 (3)
C13—C14—C15—C16	176.5 (2)	C15—C14—C19—C18	1.5 (3)
C2—N1—C6—N2	−179.19 (17)	C13—C14—C19—C18	−177.4 (2)
C2—N1—C6—C5	0.0 (3)	C6—C5—C4—C3	−0.1 (3)
C9—N2—C6—N1	−177.63 (18)	C11—C5—C4—C3	179.3 (2)
C7—N2—C6—N1	4.5 (3)	C5—C4—C3—C2	0.4 (4)
C9—N2—C6—C5	3.2 (3)	N1—C2—C3—C4	−0.5 (4)
C7—N2—C6—C5	−174.73 (19)	C1—C2—C3—C4	178.2 (2)
O3—C17—C18—C19	178.2 (2)	C9—N2—C7—C8	98.6 (3)
C16—C17—C18—C19	−1.4 (3)	C6—N2—C7—C8	−83.5 (3)
N1—C6—C5—C4	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1	0.91 (2)	1.91 (2)	2.660 (3)	139 (2)
O3—H3O···O2i	0.82	1.90	2.721 (3)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1	0.91 (2)	1.91 (2)	2.660 (3)	139 (2)
O3—H3O⋯O2i	0.82	1.90	2.721 (3)	179

Symmetry code: (i) .