(E)-N'-[(2-Hydroxynaphthalen-1-yl)methylidene]nicotinohydrazide.

In the mol-ecule of the title compound, C(17)H(13)N(3)O(2), the naphthyl ring system and the pyridine ring form a dihedral angle of 12.2 (3)°. An intra-molecular O-H⋯N hydrogen bond generates a six-membered ring with an S(6) ring motif. This also contributes to the relative overall near planarity of the mol-ecule [r.m.s. deviation of all 22 non-H atoms = 0.107 (5) Å]. In the crystal, mol-ecules are linked through inter-molecular N-H⋯N hydrogen bonds, forming chains along the a axis.

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010 ▶); Zhu et al. (2009 ▶). For hydrazones we have reported previously, see: Liu & You (2010 ▶); Liu & Wang (2010 ▶). For related structures, see: Khaledi et al. (2009 ▶); Xu et al. (2009 ▶); Shafiq et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H13N3O2

M = 291.30

Orthorhombic,

a = 6.253 (2) Å

b = 12.335 (4) Å

c = 18.511 (7) Å

V = 1427.8 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.982, T max = 0.984

8787 measured reflections

1810 independent reflections

921 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.131

S = 0.99

1810 reflections

204 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023257/sj5164sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023257/sj5164Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023257/sj5164Isup3.cml

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

C17H13N3O2	F(000) = 608
Mr = 291.30	Dx = 1.355 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 536 reflections
a = 6.253 (2) Å	θ = 2.6–24.5°
b = 12.335 (4) Å	µ = 0.09 mm−1
c = 18.511 (7) Å	T = 298 K
V = 1427.8 (9) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	1810 independent reflections
Radiation source: fine-focus sealed tube	921 reflections with I > 2σ(I)
graphite	Rint = 0.081
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.982, Tmax = 0.984	k = −15→14
8787 measured reflections	l = −23→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0547P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
1810 reflections	Δρmax = 0.13 e Å−3
204 parameters	Δρmin = −0.13 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (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	0.7202 (5)	0.4933 (3)	0.16836 (14)	0.0776 (10)
H1	0.6042	0.5236	0.1638	0.116*
O2	0.2100 (5)	0.6667 (3)	0.21269 (15)	0.0921 (11)
N1	0.4016 (5)	0.5735 (3)	0.09932 (17)	0.0550 (9)
N2	0.2169 (6)	0.6340 (3)	0.09272 (17)	0.0556 (9)
N3	−0.3466 (6)	0.8162 (3)	0.06814 (18)	0.0623 (10)
C1	0.6656 (6)	0.4675 (3)	0.0409 (2)	0.0458 (9)
C2	0.7836 (7)	0.4540 (3)	0.1040 (2)	0.0556 (11)
C3	0.9784 (7)	0.3984 (3)	0.1031 (3)	0.0682 (13)
H3	1.0544	0.3890	0.1459	0.082*
C4	1.0576 (7)	0.3579 (3)	0.0404 (3)	0.0699 (13)
H4	1.1884	0.3220	0.0410	0.084*
C5	0.9465 (7)	0.3688 (3)	−0.0257 (3)	0.0577 (11)
C6	1.0301 (8)	0.3281 (3)	−0.0913 (3)	0.0772 (14)
H6	1.1625	0.2938	−0.0914	0.093*
C7	0.9201 (10)	0.3384 (4)	−0.1541 (3)	0.0875 (16)
H7	0.9771	0.3110	−0.1968	0.105*
C8	0.7219 (9)	0.3898 (4)	−0.1546 (2)	0.0768 (14)
H8	0.6467	0.3963	−0.1978	0.092*
C9	0.6364 (7)	0.4310 (3)	−0.0923 (2)	0.0609 (11)
H9	0.5034	0.4646	−0.0937	0.073*
C10	0.7465 (7)	0.4234 (3)	−0.0255 (2)	0.0501 (10)
C11	0.4700 (6)	0.5284 (3)	0.0414 (2)	0.0498 (10)
H11	0.3917	0.5354	−0.0011	0.060*
C12	0.1344 (7)	0.6808 (3)	0.1530 (2)	0.0592 (11)
C13	−0.0594 (7)	0.7491 (3)	0.1416 (2)	0.0532 (11)
C14	−0.1289 (10)	0.8127 (4)	0.1977 (2)	0.0980 (19)
H14	−0.0557	0.8128	0.2414	0.118*
C15	−0.3062 (10)	0.8761 (5)	0.1888 (3)	0.116 (2)
H15	−0.3548	0.9196	0.2264	0.140*
C16	−0.4116 (8)	0.8747 (4)	0.1241 (2)	0.0704 (13)
H16	−0.5343	0.9167	0.1191	0.085*
C17	−0.1735 (7)	0.7550 (3)	0.0787 (2)	0.0584 (11)
H17	−0.1266	0.7129	0.0402	0.070*
H2	0.165 (7)	0.648 (3)	0.0485 (11)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.085 (3)	0.085 (2)	0.0627 (19)	0.008 (2)	−0.0107 (17)	0.0032 (16)
O2	0.088 (3)	0.135 (3)	0.0539 (18)	0.046 (2)	−0.0086 (17)	−0.0062 (18)
N1	0.046 (2)	0.0574 (19)	0.062 (2)	0.0066 (18)	0.0041 (18)	−0.0025 (18)
N2	0.048 (2)	0.064 (2)	0.055 (2)	0.0080 (19)	0.0020 (18)	−0.0004 (18)
N3	0.055 (3)	0.064 (2)	0.068 (2)	0.004 (2)	0.0006 (19)	−0.0009 (18)
C1	0.041 (2)	0.041 (2)	0.056 (2)	−0.0007 (19)	0.0009 (19)	0.0080 (18)
C2	0.056 (3)	0.048 (2)	0.063 (3)	−0.002 (2)	−0.006 (2)	0.005 (2)
C3	0.060 (3)	0.063 (3)	0.081 (3)	0.006 (3)	−0.019 (3)	0.013 (3)
C4	0.047 (3)	0.045 (2)	0.117 (4)	0.007 (2)	−0.008 (3)	0.011 (3)
C5	0.048 (3)	0.038 (2)	0.087 (3)	−0.004 (2)	0.006 (3)	0.003 (2)
C6	0.054 (3)	0.061 (3)	0.117 (4)	−0.006 (3)	0.031 (3)	−0.014 (3)
C7	0.092 (4)	0.081 (3)	0.089 (4)	−0.007 (3)	0.028 (3)	−0.027 (3)
C8	0.089 (4)	0.078 (3)	0.064 (3)	−0.007 (3)	0.005 (3)	−0.001 (2)
C9	0.066 (3)	0.061 (2)	0.056 (2)	−0.001 (2)	0.004 (2)	−0.002 (2)
C10	0.045 (3)	0.041 (2)	0.064 (3)	−0.002 (2)	0.007 (2)	0.0061 (19)
C11	0.050 (3)	0.050 (2)	0.049 (2)	0.001 (2)	−0.0025 (19)	0.002 (2)
C12	0.056 (3)	0.070 (3)	0.052 (3)	0.010 (3)	0.004 (2)	−0.001 (2)
C13	0.058 (3)	0.054 (2)	0.047 (2)	0.008 (2)	0.004 (2)	0.0012 (19)
C14	0.122 (5)	0.121 (4)	0.051 (3)	0.066 (4)	−0.008 (3)	−0.018 (3)
C15	0.153 (6)	0.144 (5)	0.052 (3)	0.092 (5)	0.008 (3)	−0.010 (3)
C16	0.068 (3)	0.074 (3)	0.070 (3)	0.020 (3)	0.011 (3)	0.009 (3)
C17	0.052 (3)	0.063 (3)	0.061 (3)	0.003 (2)	0.001 (2)	−0.012 (2)

O1—C2	1.346 (4)	C6—C7	1.357 (7)
O1—H1	0.8200	C6—H6	0.9300
O2—C12	1.214 (4)	C7—C8	1.393 (7)
N1—C11	1.282 (4)	C7—H7	0.9300
N1—N2	1.381 (4)	C8—C9	1.370 (6)
N2—C12	1.358 (5)	C8—H8	0.9300
N2—H2	0.898 (10)	C9—C10	1.417 (5)
N3—C16	1.326 (5)	C9—H9	0.9300
N3—C17	1.334 (5)	C11—H11	0.9300
C1—C2	1.392 (5)	C12—C13	1.491 (6)
C1—C11	1.435 (5)	C13—C17	1.367 (5)
C1—C10	1.436 (5)	C13—C14	1.372 (5)
C2—C3	1.398 (6)	C14—C15	1.366 (6)
C3—C4	1.357 (6)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.368 (6)
C4—C5	1.414 (6)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.414 (6)	C17—H17	0.9300
C5—C10	1.421 (5)
C2—O1—H1	109.5	C7—C8—H8	119.7
C11—N1—N2	116.1 (3)	C8—C9—C10	121.4 (4)
C12—N2—N1	118.3 (3)	C8—C9—H9	119.3
C12—N2—H2	122 (3)	C10—C9—H9	119.3
N1—N2—H2	119 (3)	C9—C10—C5	117.2 (4)
C16—N3—C17	116.2 (4)	C9—C10—C1	123.4 (4)
C2—C1—C11	120.6 (4)	C5—C10—C1	119.4 (4)
C2—C1—C10	119.1 (4)	N1—C11—C1	121.1 (4)
C11—C1—C10	120.2 (4)	N1—C11—H11	119.4
O1—C2—C1	122.9 (4)	C1—C11—H11	119.4
O1—C2—C3	116.3 (4)	O2—C12—N2	122.6 (4)
C1—C2—C3	120.7 (4)	O2—C12—C13	121.8 (4)
C4—C3—C2	120.5 (4)	N2—C12—C13	115.6 (4)
C4—C3—H3	119.7	C17—C13—C14	116.6 (4)
C2—C3—H3	119.7	C17—C13—C12	125.1 (4)
C3—C4—C5	121.8 (4)	C14—C13—C12	118.3 (4)
C3—C4—H4	119.1	C15—C14—C13	119.6 (5)
C5—C4—H4	119.1	C15—C14—H14	120.2
C6—C5—C4	121.9 (5)	C13—C14—H14	120.2
C6—C5—C10	119.7 (4)	C14—C15—C16	119.3 (5)
C4—C5—C10	118.4 (4)	C14—C15—H15	120.4
C7—C6—C5	121.0 (5)	C16—C15—H15	120.4
C7—C6—H6	119.5	N3—C16—C15	122.9 (5)
C5—C6—H6	119.5	N3—C16—H16	118.5
C6—C7—C8	120.0 (5)	C15—C16—H16	118.5
C6—C7—H7	120.0	N3—C17—C13	125.4 (4)
C8—C7—H7	120.0	N3—C17—H17	117.3
C9—C8—C7	120.7 (5)	C13—C17—H17	117.3
C9—C8—H8	119.7

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.565 (4)	146
N2—H2···N3i	0.90 (1)	2.20 (2)	3.066 (5)	161 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.565 (4)	146
N2—H2⋯N3i	0.90 (1)	2.20 (2)	3.066 (5)	161 (4)

Symmetry code: (i) .