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

Liu, S.-Y.; Guo, Q.-Q.; Hao, Y.-M.; Wang, X.-L.

doi:10.1107/S1600536811023257

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1756

doi:10.1107/S1600536811023257

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

Shi-Yong Liu,^a ^* Qin-Qin Guo,^a Yu-Mei Hao ^b and Xiao-Ling Wang ^c

^aCollege of Chemistry and Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China, ^bDepartment of Chemistry, Baicheng Normal University, Baicheng 137000, People's Republic of China, and ^cDepartment of Chemistry, Liaoning Normal University, Dalian 116029, People's Republic of China
^*Correspondence e-mail: liushiyong2010@yahoo.cn

(Received 13 June 2011; accepted 15 June 2011; online 22 June 2011)

In the molecule of the title compound, C₁₇H₁₃N₃O₂, the naphthyl ring system and the pyridine ring form a dihedral angle of 12.2 (3)°. An intramolecular 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 molecule [r.m.s. deviation of all 22 non-H atoms = 0.107 (5) Å]. In the crystal, molecules are linked through intermolecular 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_r = 291.30
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.131
S = 0.99
1810 reflections
204 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.13 e Å⁻³

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

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811023257/sj5164sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811023257/sj5164Isup3.cml

checkCIF report

Comment top

Considerable attention has been focused on hydrazones and their medicinal applications (Hillmer et al., 2010; Zhu et al., 2009). A study of the crystal structures of such compounds is of particular interest (Khaledi et al., 2009). As a continuation of our work on the preparation and structure of such compounds (Liu & You, 2010; Liu & Wang, 2010), we report herein the crystal structure of the title compound, a new hydrazone.

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the C1—C10 naphthyl ring and the C13—C17/N3 pyridine ring is 12.2 (3) °. An intramolecular O1—H1···N1 hydrogen bond forms a six-membered ring, with an S(6) ring motif [Fig. 1] and contributes to the overall planarity of the molecule (Bernstein et al., 1995). All the bond lengths are comparable to those observed in related structures (Xu et al., 2009; Shafiq et al., 2009) and those we reported previously. In the crystal structure, molecules are linked through intermolecular N2–H2···N3 hydrogen bonds (Table 1), to form chains along the a axis (Fig. 2).

Related literature top

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 top

The title compound was prepared by the condensation reaction of 2-hydroxy-1-naphthaldehyde (1.0 mmol, 0.172 g) and nicotinohydrazide (1.0 mmol, 0.137 g) in methanol (50 ml) at ambient temperature. Colourless block-shaped single crystals suitable for X-ray structural determination were obtained by slow evaporation of the solution for a few days.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius and the intramolecular hydrogen bond is drawn as a dashed line.
	Fig. 2. The molecular packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

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

Crystal data top

C₁₇H₁₃N₃O₂	F(000) = 608
M_r = 291.30	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0547P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
1810 reflections	Δρ_max = 0.13 e Å⁻³
204 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₁₃N₃O₂	V = 1427.8 (9) Å³
M_r = 291.30	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.253 (2) Å	µ = 0.09 mm⁻¹
b = 12.335 (4) Å	T = 298 K
c = 18.511 (7) Å	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1810 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	921 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.984	R_int = 0.081
8787 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.13 e Å⁻³
1810 reflections	Δρ_min = −0.13 e Å⁻³
204 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃N₃O₂
M_r	291.30
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	6.253 (2), 12.335 (4), 18.511 (7)
V (Å³)	1427.8 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.982, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8787, 1810, 921
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.131, 0.99
No. of reflections	1810
No. of parameters	204
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

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

Hydrogen-bond geometry (Å, º) top

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	0.898 (10)	2.204 (19)	3.066 (5)	161 (4)

Symmetry code: (i) x+1/2, −y+3/2, −z.

Acknowledgements

The authors acknowledge the Undergraduate Innovation Group Project of Zhejiang Province (project No. 2010R428015).

References

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