3-Hy-droxy-N'-[(E)-3-pyridyl-methyl-idene]-2-naphtho-hydrazide.

The title compound, C(17)H(13)N(3)O(2), displays an E configuration about the C=N bond. The mean planes of the pyridine and benzene rings make a dihedral angle of 31.2 (2)°. An intra-molecular O-H⋯O hydrogen bond is observed. In the crystal, inter-molecular N-H⋯N hydrogen bonding links the mol-ecules into a chain along [101].

Related literature

For related structures, see: Lv et al. (2006 ▶); Tarafder et al. (2002 ▶); Zhou et al. (2009 ▶); Huang (2009 ▶); Shafiq et al. (2009 ▶); Liang et al. (2008 ▶).

Experimental

Crystal data

C17H13N3O2

M = 291.30

Orthorhombic,

a = 11.0976 (11) Å

b = 10.4422 (9) Å

c = 23.9903 (17) Å

V = 2780.1 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.39 × 0.38 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.971

10663 measured reflections

2451 independent reflections

1486 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.07

2451 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025591/kp2338sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025591/kp2338Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025591/kp2338Isup3.cml

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

C17H13N3O2	F(000) = 1216
Mr = 291.30	Dx = 1.392 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2315 reflections
a = 11.0976 (11) Å	θ = 2.5–24.7°
b = 10.4422 (9) Å	µ = 0.09 mm−1
c = 23.9903 (17) Å	T = 298 K
V = 2780.1 (4) Å3	Block, brown
Z = 8	0.39 × 0.38 × 0.32 mm

Bruker SMART CCD area-detector diffractometer	2451 independent reflections
Radiation source: fine-focus sealed tube	1486 reflections with I > 2σ(I)
graphite	Rint = 0.043
phi and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.964, Tmax = 0.971	k = −12→12
10663 measured reflections	l = −16→28

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.033P)2 + 1.2301P] where P = (Fo2 + 2Fc2)/3
2451 reflections	(Δ/σ)max = 0.018
200 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.72696 (12)	0.13202 (13)	0.68223 (5)	0.0454 (4)
H1	0.6567	0.1573	0.6719	0.055*
N2	0.73782 (12)	0.03490 (13)	0.72100 (5)	0.0441 (4)
N3	0.51884 (13)	−0.26353 (14)	0.83141 (6)	0.0517 (4)
O1	0.92858 (10)	0.16623 (12)	0.67932 (5)	0.0587 (4)
O2	0.99947 (10)	0.37468 (13)	0.62980 (5)	0.0631 (4)
H2	1.0011	0.3162	0.6526	0.095*
C1	0.89726 (14)	0.36595 (16)	0.59886 (7)	0.0436 (5)
C2	0.88220 (15)	0.44499 (16)	0.55447 (7)	0.0478 (5)
H2A	0.9415	0.5053	0.5466	0.057*
C3	0.77958 (15)	0.43855 (15)	0.51990 (6)	0.0425 (5)
C4	0.76205 (18)	0.51752 (17)	0.47290 (7)	0.0559 (5)
H4	0.8195	0.5790	0.4640	0.067*
C5	0.66274 (19)	0.50506 (18)	0.44061 (7)	0.0611 (6)
H5	0.6528	0.5587	0.4100	0.073*
C6	0.57495 (18)	0.41305 (17)	0.45245 (7)	0.0594 (6)
H6	0.5079	0.4048	0.4295	0.071*
C7	0.58781 (16)	0.33592 (16)	0.49747 (7)	0.0513 (5)
H7	0.5288	0.2754	0.5054	0.062*
C8	0.68986 (15)	0.34632 (15)	0.53254 (6)	0.0409 (4)
C9	0.70638 (15)	0.26731 (15)	0.57943 (6)	0.0415 (5)
H9	0.6471	0.2076	0.5881	0.050*
C10	0.80619 (14)	0.27488 (15)	0.61284 (6)	0.0378 (4)
C11	0.82639 (15)	0.18724 (16)	0.66058 (6)	0.0420 (5)
C12	0.64006 (16)	−0.00150 (16)	0.74330 (6)	0.0447 (5)
H12	0.5686	0.0406	0.7347	0.054*
C13	0.63850 (14)	−0.10870 (15)	0.78229 (6)	0.0388 (4)
C14	0.74226 (16)	−0.16753 (17)	0.80160 (7)	0.0478 (5)
H14	0.8176	−0.1357	0.7918	0.057*
C16	0.62105 (17)	−0.31857 (17)	0.84855 (7)	0.0539 (5)
H15	0.6158	−0.3916	0.8706	0.065*
C17	0.53001 (16)	−0.15897 (18)	0.79985 (7)	0.0486 (5)
H17	0.4599	−0.1172	0.7890	0.058*
C15	0.73317 (16)	−0.27280 (17)	0.83522 (7)	0.0525 (5)
H18	0.8020	−0.3128	0.8489	0.063*

	U11	U22	U33	U12	U13	U23
N1	0.0402 (8)	0.0517 (8)	0.0444 (7)	0.0054 (7)	0.0001 (6)	0.0108 (7)
N2	0.0446 (8)	0.0480 (8)	0.0397 (7)	0.0038 (7)	0.0002 (7)	0.0052 (7)
N3	0.0461 (8)	0.0557 (9)	0.0533 (8)	−0.0090 (8)	0.0024 (7)	0.0052 (8)
O1	0.0406 (7)	0.0751 (8)	0.0603 (7)	0.0044 (7)	−0.0062 (6)	0.0105 (7)
O2	0.0445 (7)	0.0711 (8)	0.0737 (8)	−0.0115 (7)	−0.0106 (6)	0.0042 (7)
C1	0.0365 (9)	0.0458 (9)	0.0486 (10)	0.0007 (8)	0.0019 (8)	−0.0083 (8)
C2	0.0469 (10)	0.0396 (9)	0.0569 (10)	−0.0067 (9)	0.0099 (9)	−0.0016 (9)
C3	0.0494 (10)	0.0368 (9)	0.0414 (9)	0.0028 (8)	0.0086 (8)	−0.0026 (8)
C4	0.0716 (13)	0.0470 (10)	0.0490 (10)	0.0013 (10)	0.0134 (10)	0.0065 (9)
C5	0.0886 (14)	0.0533 (11)	0.0415 (10)	0.0139 (11)	0.0013 (10)	0.0065 (9)
C6	0.0766 (13)	0.0561 (11)	0.0455 (10)	0.0086 (11)	−0.0126 (10)	−0.0063 (9)
C7	0.0564 (11)	0.0456 (10)	0.0518 (10)	0.0003 (9)	−0.0067 (9)	−0.0038 (9)
C8	0.0472 (10)	0.0384 (9)	0.0372 (8)	0.0035 (8)	0.0021 (8)	−0.0045 (8)
C9	0.0426 (10)	0.0385 (9)	0.0434 (9)	−0.0058 (8)	0.0038 (8)	−0.0025 (8)
C10	0.0366 (9)	0.0372 (9)	0.0394 (8)	0.0006 (8)	0.0036 (7)	−0.0029 (7)
C11	0.0389 (9)	0.0458 (10)	0.0412 (9)	0.0008 (8)	0.0014 (8)	−0.0041 (8)
C12	0.0416 (10)	0.0499 (10)	0.0427 (9)	0.0049 (9)	−0.0043 (8)	0.0042 (8)
C13	0.0376 (9)	0.0444 (9)	0.0344 (8)	0.0011 (8)	−0.0011 (7)	−0.0007 (8)
C14	0.0373 (9)	0.0569 (11)	0.0491 (9)	−0.0016 (9)	0.0003 (8)	0.0072 (9)
C16	0.0593 (12)	0.0473 (10)	0.0552 (11)	−0.0049 (10)	−0.0015 (9)	0.0075 (9)
C17	0.0395 (10)	0.0602 (11)	0.0462 (9)	0.0004 (9)	−0.0042 (8)	−0.0008 (9)
C15	0.0427 (10)	0.0543 (11)	0.0606 (11)	0.0043 (9)	−0.0052 (9)	0.0130 (9)

N1—C11	1.349 (2)	C6—C7	1.355 (2)
N1—N2	1.3814 (17)	C6—H6	0.9300
N1—H1	0.8600	C7—C8	1.415 (2)
N2—C12	1.268 (2)	C7—H7	0.9300
N3—C17	1.334 (2)	C8—C9	1.407 (2)
N3—C16	1.336 (2)	C9—C10	1.370 (2)
O1—C11	1.2395 (19)	C9—H9	0.9300
O2—C1	1.3586 (19)	C10—C11	1.483 (2)
O2—H2	0.8200	C12—C13	1.459 (2)
C1—C2	1.358 (2)	C12—H12	0.9300
C1—C10	1.428 (2)	C13—C17	1.379 (2)
C2—C3	1.411 (2)	C13—C14	1.385 (2)
C2—H2A	0.9300	C14—C15	1.367 (2)
C3—C4	1.410 (2)	C14—H14	0.9300
C3—C8	1.418 (2)	C16—C15	1.371 (2)
C4—C5	1.353 (3)	C16—H15	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.397 (3)	C15—H18	0.9300
C5—H5	0.9300
C11—N1—N2	120.11 (13)	C7—C8—C3	119.14 (15)
C11—N1—H1	119.9	C10—C9—C8	122.64 (15)
N2—N1—H1	119.9	C10—C9—H9	118.7
C12—N2—N1	115.43 (14)	C8—C9—H9	118.7
C17—N3—C16	116.59 (15)	C9—C10—C1	118.26 (14)
C1—O2—H2	109.5	C9—C10—C11	122.59 (14)
C2—C1—O2	119.38 (15)	C1—C10—C11	119.04 (14)
C2—C1—C10	120.14 (15)	O1—C11—N1	122.22 (15)
O2—C1—C10	120.48 (15)	O1—C11—C10	121.84 (15)
C1—C2—C3	122.12 (15)	N1—C11—C10	115.94 (14)
C1—C2—H2A	118.9	N2—C12—C13	120.71 (15)
C3—C2—H2A	118.9	N2—C12—H12	119.6
C4—C3—C2	123.62 (16)	C13—C12—H12	119.6
C4—C3—C8	118.11 (15)	C17—C13—C14	117.05 (15)
C2—C3—C8	118.26 (14)	C17—C13—C12	119.88 (15)
C5—C4—C3	120.91 (17)	C14—C13—C12	123.02 (15)
C5—C4—H4	119.5	C15—C14—C13	119.52 (16)
C3—C4—H4	119.5	C15—C14—H14	120.2
C4—C5—C6	121.16 (17)	C13—C14—H14	120.2
C4—C5—H5	119.4	N3—C16—C15	123.29 (17)
C6—C5—H5	119.4	N3—C16—H15	118.4
C7—C6—C5	119.82 (18)	C15—C16—H15	118.4
C7—C6—H6	120.1	N3—C17—C13	124.45 (16)
C5—C6—H6	120.1	N3—C17—H17	117.8
C6—C7—C8	120.84 (17)	C13—C17—H17	117.8
C6—C7—H7	119.6	C14—C15—C16	119.00 (17)
C8—C7—H7	119.6	C14—C15—H18	120.5
C9—C8—C7	122.31 (15)	C16—C15—H18	120.5
C9—C8—C3	118.54 (15)
C11—N1—N2—C12	172.76 (15)	O2—C1—C10—C9	−178.18 (15)
O2—C1—C2—C3	178.39 (15)	C2—C1—C10—C11	178.32 (15)
C10—C1—C2—C3	−1.8 (2)	O2—C1—C10—C11	−1.9 (2)
C1—C2—C3—C4	−178.81 (16)	N2—N1—C11—O1	−9.7 (2)
C1—C2—C3—C8	0.2 (2)	N2—N1—C11—C10	170.29 (13)
C2—C3—C4—C5	178.62 (17)	C9—C10—C11—O1	156.80 (16)
C8—C3—C4—C5	−0.4 (2)	C1—C10—C11—O1	−19.4 (2)
C3—C4—C5—C6	−0.5 (3)	C9—C10—C11—N1	−23.2 (2)
C4—C5—C6—C7	1.1 (3)	C1—C10—C11—N1	160.67 (14)
C5—C6—C7—C8	−0.6 (3)	N1—N2—C12—C13	176.15 (13)
C6—C7—C8—C9	−179.64 (16)	N2—C12—C13—C17	−170.56 (16)
C6—C7—C8—C3	−0.3 (2)	N2—C12—C13—C14	6.9 (2)
C4—C3—C8—C9	−179.83 (15)	C17—C13—C14—C15	1.8 (2)
C2—C3—C8—C9	1.1 (2)	C12—C13—C14—C15	−175.73 (15)
C4—C3—C8—C7	0.8 (2)	C17—N3—C16—C15	0.0 (3)
C2—C3—C8—C7	−178.27 (15)	C16—N3—C17—C13	2.9 (2)
C7—C8—C9—C10	178.50 (16)	C14—C13—C17—N3	−3.8 (2)
C3—C8—C9—C10	−0.9 (2)	C12—C13—C17—N3	173.85 (15)
C8—C9—C10—C1	−0.7 (2)	C13—C14—C15—C16	0.7 (3)
C8—C9—C10—C11	−176.86 (15)	N3—C16—C15—C14	−1.7 (3)
C2—C1—C10—C9	2.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.87	2.6015 (18)	147
N1—H1···N3i	0.86	2.12	2.956 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.87	2.6015 (18)	147
N1—H1⋯N3i	0.86	2.12	2.956 (2)	165

Symmetry code: (i) .