3-Hy­droxy-N′-[(E)-3-pyridyl­methyl­idene]-2-naphtho­hydrazide

Li, C.; Zhang, X.; Wu, Q.; Yin, H.

doi:10.1107/S1600536811025591

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1912

doi:10.1107/S1600536811025591

Open

access

3-Hydroxy-N′-[(E)-3-pyridylmethylidene]-2-naphthohydrazide

Chuan Li,^a Xiuyun Zhang,^a Qingkun Wu ^a and Handong Yin ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 17 June 2011; accepted 29 June 2011; online 6 July 2011)

The title compound, C₁₇H₁₃N₃O₂, 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 intramolecular O—H⋯O hydrogen bond is observed. In the crystal, intermolecular N—H⋯N hydrogen bonding links the molecules 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_r = 291.30
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.07
2451 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025591/kp2338sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811025591/kp2338Isup3.cml

checkCIF report

Comment top

Schiff bases have been extensively investigated because of their important applications in coordination chemistry, catalysis and biological processes. (Lv et al., 2006; Tarafder et al., 2002; Zhou et al., 2009). In continuation of our research of organotin derivatives, the title compound, a novel Schiff base, was prepared and its crystal structure presented (Fig. 1). The structure of the molecule shows an E configuration about the C=N bond. The mean planes of the pyridine and benzene rings make the dihedral angle of 31.20 (15)°. Intramolecular O—H···O hydrogen bond was observed (Fig. 1 and Table 1). All bond lengths and angles are normal and correspond to those observed in the related componds (Huang (2009); Shafiq et al., 2009; Liang et al., 2008). In the crystal structure, intermolecular N—H···N hydrogen bonds link the molecules into a chain (Fig.2 and Table 1).

Related literature top

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 top

The methanol solution of 3-pyridinecarboxaldehyde(0.2 mol) was added dropwise to a solution of 3-hydroxy-2-naphthohydrazide(0.2 mol) in mehtanol. Then the mixture was stirred at room temperature for 6 h, during which time a brown precipitate was observed. The precipitate was filtrated off and the obtained solid was recrystallised from methanol. Anal. Calc (%) for C₁₇H₁₃N₃O₂ (291.30): C, 70.11; H, 4.45; N, 14.48. Found (%): C, 70.09; H, 4.50; N, 14.43.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids. An O—H···O intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. View of the chain formed by N—H···N hydrogen bond.

3-Hydroxy-N'-[(E)-3-pyridylmethylidene]-2-naphthohydrazide top

Crystal data top

C₁₇H₁₃N₃O₂	F(000) = 1216
M_r = 291.30	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.033P)² + 1.2301P] where P = (F_o² + 2F_c²)/3
2451 reflections	(Δ/σ)_max = 0.018
200 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₃N₃O₂	V = 2780.1 (4) Å³
M_r = 291.30	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.0976 (11) Å	µ = 0.09 mm⁻¹
b = 10.4422 (9) Å	T = 298 K
c = 23.9903 (17) Å	0.39 × 0.38 × 0.32 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2451 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1486 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.971	R_int = 0.043
10663 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.07	Δρ_max = 0.16 e Å⁻³
2451 reflections	Δρ_min = −0.18 e Å⁻³
200 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃N₃O₂
M_r	291.30
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	11.0976 (11), 10.4422 (9), 23.9903 (17)
V (Å³)	2780.1 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.39 × 0.38 × 0.32

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.964, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	10663, 2451, 1486
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.07
No. of reflections	2451
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+3/2.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20771053), the National Basic Research Program (No. 2010CB234601) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huang, H.-T. (2009). Acta Cryst. E65, o892. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liang, Q.-F., Feng, H.-M. & Li, F.-Q. (2008). Acta Cryst. E64, o1008. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lv, J., Liu, T., Cai, S., Wang, X., Liu, L. & Wang, Y. (2006). J. Inorg. Biochem. 100, 1888–1896. Web of Science CrossRef PubMed CAS Google Scholar
Shafiq, Z., Yaqub, M., Tahir, M. N., Nawaz, M. H. & Iqbal, M. S. (2009). Acta Cryst. E65, o2845–o2846. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tarafder, M. T. H., Jin, K. T., Crouse, K. A., Ali, A. M. & Yamin, B. M. (2002). Polyhedron, 21, 2547–2554. Web of Science CSD CrossRef CAS Google Scholar
Zhou, J.-C., Li, N.-X., Zhang, C.-M. & Zhang, Z.-Y. (2009). Acta Cryst. E65, o1949. Web of Science CSD CrossRef IUCr Journals Google Scholar