(E)-N′-[(2-Hy­droxy-1-naphthalen-1-yl)methyl­idene]-3-methyl­benzohydrazide

Liu, S.-Y.; Sun, S.-S.; Zheng, T.-T.; Zheng, X.-L.; Zhao, X.-F.; Li, X.-F.

doi:10.1107/S1600536811010361

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o965

doi:10.1107/S1600536811010361

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(E)-N′-[(2-Hydroxy-1-naphthalen-1-yl)methylidene]-3-methylbenzohydrazide

Shi-Yong Liu,^a ^* Shan-Shan Sun,^a Ting-Ting Zheng,^a Xiang-Lei Zheng,^a Xiao-Feng Zhao ^a and Xiao-Fang Li ^b

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

(Received 18 March 2011; accepted 19 March 2011; online 26 March 2011)

In the title compound, C₁₉H₁₆N₂O₂, the benzene ring and naphthyl ring system are inclined at a dihedral angle of 16.1 (3)°. An intramolecular O—H⋯N hydrogen bond influences the molecular conformation. In the crystal, molecules are linked through N—H⋯O hydrogen bonds into chains running along the a axis.

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010 ); Raj et al. (2007 ). For hydrazones we have reported previously, see: Liu & You (2010 ); Liu & Wang (2010 ). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009 ). For related structures, see: Xu et al. (2009 ); Shafiq et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₆N₂O₂
M_r = 304.34
Monoclinic, P 2₁ /n
a = 7.1927 (11) Å
b = 31.042 (4) Å
c = 7.3557 (11) Å
β = 108.455 (2)°
V = 1557.9 (4) 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 = 0.983, T_max = 0.985
8247 measured reflections
3295 independent reflections
1736 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.166
S = 1.04
3295 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.90 (1)	2.00 (1)	2.869 (3)	163 (3)
O1—H1⋯N1	0.82	1.85	2.567 (3)	146
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536811010361/sj5120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010361/sj5120Isup2.hkl

checkCIF report

Comment top

Considerable attention has been focused on hydrazones and their medicinal applications (Hillmer et al., 2010; Raj et al., 2007). The crystal structures of such compounds are of particular interest (Vijayakumar et al., 2009). As a continuation of our work on similar 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 benzene ring and the naphthyl ring system are inclined at a dihedral angle of 16.1 (3) °. The dihedral angle between the C1—C10 benzene ring and the C13—C18 naphthyl ring is 16.1 (3)°. 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 N–H···O hydrogen bonds, to form one-dimensional chains running along the a axis (Fig. 2 and Table 1).

Related literature top

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010); Raj et al. (2007). For hydrazones we have reported previously, see: Liu & You (2010); Liu & Wang (2010). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009). For related structures, see: Xu et al. (2009); Shafiq et al. (2009).

Experimental top

The title compound was prepared by the condensation reaction of 2-hydroxy-1-naphthaldehyde (0.05 mol, 8.6 g) and 3-methylbenzohydrazide (0.05 mol, 7.5 g) in anhydrous methanol (200 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 period of a week.

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-Hydroxy-1-naphthalen-1-yl)methylidene]- 3-methylbenzohydrazide top

Crystal data top

C₁₉H₁₆N₂O₂	F(000) = 640
M_r = 304.34	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2077 reflections
a = 7.1927 (11) Å	θ = 2.6–28.2°
b = 31.042 (4) Å	µ = 0.09 mm⁻¹
c = 7.3557 (11) Å	T = 298 K
β = 108.455 (2)°	Block, colourless
V = 1557.9 (4) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3295 independent reflections
Radiation source: fine-focus sealed tube	1736 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans	θ_max = 27.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
T_min = 0.983, T_max = 0.985	k = −33→39
8247 measured reflections	l = −9→9

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0465P)² + 1.2072P] where P = (F_o² + 2F_c²)/3
3295 reflections	(Δ/σ)_max < 0.001
214 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O₂	V = 1557.9 (4) Å³
M_r = 304.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1927 (11) Å	µ = 0.09 mm⁻¹
b = 31.042 (4) Å	T = 298 K
c = 7.3557 (11) Å	0.20 × 0.20 × 0.18 mm
β = 108.455 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3295 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1736 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.985	R_int = 0.045
8247 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	1 restraint
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.17 e Å⁻³
3295 reflections	Δρ_min = −0.20 e Å⁻³
214 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
N1	0.9044 (4)	0.21446 (7)	0.1747 (4)	0.0379 (6)
N2	0.8759 (4)	0.24304 (8)	0.0245 (4)	0.0390 (7)
O1	0.9690 (4)	0.19721 (7)	0.5307 (3)	0.0551 (7)
H1	0.9671	0.2122	0.4383	0.083*
O2	1.0611 (3)	0.29377 (6)	0.2203 (3)	0.0471 (6)
C1	0.8618 (4)	0.14411 (9)	0.2810 (4)	0.0337 (7)
C2	0.9202 (5)	0.15626 (10)	0.4718 (4)	0.0400 (8)
C3	0.9317 (5)	0.12581 (12)	0.6167 (5)	0.0525 (9)
H3	0.9674	0.1347	0.7439	0.063*
C4	0.8914 (5)	0.08380 (12)	0.5729 (5)	0.0542 (10)
H4	0.9004	0.0642	0.6707	0.065*
C5	0.8357 (5)	0.06922 (10)	0.3811 (5)	0.0422 (8)
C6	0.7989 (5)	0.02510 (11)	0.3339 (6)	0.0587 (11)
H6	0.8090	0.0052	0.4312	0.070*
C7	0.7494 (6)	0.01134 (11)	0.1513 (7)	0.0654 (12)
H7	0.7285	−0.0178	0.1234	0.079*
C8	0.7298 (6)	0.04084 (11)	0.0046 (6)	0.0622 (11)
H8	0.6937	0.0313	−0.1216	0.075*
C9	0.7629 (5)	0.08375 (10)	0.0430 (5)	0.0497 (9)
H9	0.7481	0.1029	−0.0577	0.060*
C10	0.8191 (4)	0.09950 (9)	0.2322 (4)	0.0358 (7)
C11	0.8430 (4)	0.17606 (9)	0.1302 (4)	0.0360 (7)
H11	0.7864	0.1685	0.0023	0.043*
C12	0.9562 (5)	0.28269 (9)	0.0607 (4)	0.0355 (7)
C13	0.9074 (4)	0.31232 (9)	−0.1072 (4)	0.0330 (7)
C14	0.8915 (4)	0.35600 (9)	−0.0735 (5)	0.0385 (8)
H14	0.9137	0.3654	0.0517	0.046*
C15	0.8436 (5)	0.38593 (10)	−0.2206 (5)	0.0456 (9)
C16	0.8164 (5)	0.37093 (12)	−0.4034 (5)	0.0551 (10)
H16	0.7840	0.3904	−0.5048	0.066*
C17	0.8357 (5)	0.32802 (12)	−0.4401 (5)	0.0560 (10)
H17	0.8191	0.3190	−0.5648	0.067*
C18	0.8798 (5)	0.29812 (10)	−0.2929 (5)	0.0421 (8)
H18	0.8906	0.2690	−0.3180	0.051*
C19	0.8209 (6)	0.43299 (10)	−0.1815 (6)	0.0701 (12)
H19A	0.9126	0.4496	−0.2228	0.105*
H19B	0.8456	0.4372	−0.0466	0.105*
H19C	0.6899	0.4421	−0.2501	0.105*
H2	0.782 (3)	0.2362 (10)	−0.085 (3)	0.048 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0403 (16)	0.0307 (14)	0.0373 (15)	0.0000 (12)	0.0046 (12)	0.0056 (12)
N2	0.0448 (17)	0.0299 (14)	0.0311 (16)	−0.0027 (12)	−0.0040 (13)	0.0032 (12)
O1	0.0730 (18)	0.0479 (14)	0.0415 (14)	−0.0114 (13)	0.0139 (14)	−0.0084 (11)
O2	0.0525 (15)	0.0393 (13)	0.0358 (13)	−0.0018 (11)	−0.0055 (11)	−0.0021 (10)
C1	0.0314 (17)	0.0342 (17)	0.0336 (17)	0.0031 (13)	0.0074 (14)	0.0037 (13)
C2	0.039 (2)	0.0409 (19)	0.0386 (19)	0.0010 (15)	0.0110 (16)	0.0014 (15)
C3	0.059 (2)	0.065 (2)	0.0294 (19)	0.0026 (19)	0.0086 (17)	0.0098 (17)
C4	0.053 (2)	0.057 (2)	0.053 (2)	0.0070 (18)	0.0164 (19)	0.0223 (19)
C5	0.0315 (18)	0.0382 (19)	0.056 (2)	0.0047 (14)	0.0121 (16)	0.0126 (16)
C6	0.049 (2)	0.041 (2)	0.087 (3)	0.0041 (17)	0.021 (2)	0.022 (2)
C7	0.067 (3)	0.033 (2)	0.094 (3)	−0.0100 (19)	0.023 (3)	−0.005 (2)
C8	0.071 (3)	0.042 (2)	0.072 (3)	−0.0121 (19)	0.021 (2)	−0.012 (2)
C9	0.056 (2)	0.0386 (19)	0.052 (2)	−0.0084 (16)	0.0147 (19)	−0.0020 (16)
C10	0.0284 (18)	0.0361 (17)	0.042 (2)	0.0035 (13)	0.0104 (15)	0.0034 (14)
C11	0.0352 (19)	0.0351 (17)	0.0339 (18)	0.0015 (14)	0.0056 (15)	0.0023 (14)
C12	0.0378 (19)	0.0307 (17)	0.0336 (19)	0.0043 (14)	0.0051 (15)	−0.0026 (14)
C13	0.0312 (17)	0.0301 (16)	0.0345 (18)	−0.0003 (13)	0.0056 (14)	0.0007 (13)
C14	0.0356 (19)	0.0314 (16)	0.045 (2)	−0.0033 (14)	0.0074 (15)	−0.0004 (14)
C15	0.0315 (19)	0.0367 (19)	0.066 (3)	−0.0003 (14)	0.0114 (17)	0.0126 (17)
C16	0.043 (2)	0.058 (2)	0.059 (3)	−0.0010 (18)	0.0089 (19)	0.0244 (19)
C17	0.055 (2)	0.073 (3)	0.039 (2)	−0.003 (2)	0.0122 (18)	0.0092 (19)
C18	0.042 (2)	0.0399 (18)	0.043 (2)	−0.0014 (15)	0.0107 (16)	−0.0012 (15)
C19	0.059 (3)	0.036 (2)	0.114 (4)	0.0054 (18)	0.027 (3)	0.019 (2)

Geometric parameters (Å, º) top

N1—C11	1.277 (4)	C8—C9	1.367 (4)
N1—N2	1.380 (3)	C8—H8	0.9300
N2—C12	1.350 (4)	C9—C10	1.408 (4)
N2—H2	0.898 (10)	C9—H9	0.9300
O1—C2	1.353 (4)	C11—H11	0.9300
O1—H1	0.8200	C12—C13	1.490 (4)
O2—C12	1.227 (3)	C13—C18	1.388 (4)
C1—C2	1.384 (4)	C13—C14	1.390 (4)
C1—C10	1.439 (4)	C14—C15	1.384 (4)
C1—C11	1.462 (4)	C14—H14	0.9300
C2—C3	1.407 (4)	C15—C16	1.377 (5)
C3—C4	1.352 (5)	C15—C19	1.508 (4)
C3—H3	0.9300	C16—C17	1.375 (5)
C4—C5	1.413 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.385 (4)
C5—C6	1.417 (5)	C17—H17	0.9300
C5—C10	1.419 (4)	C18—H18	0.9300
C6—C7	1.346 (5)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.388 (5)	C19—H19C	0.9600
C7—H7	0.9300

C11—N1—N2	116.3 (3)	C9—C10—C1	123.5 (3)
C12—N2—N1	118.8 (2)	C5—C10—C1	119.1 (3)
C12—N2—H2	123 (2)	N1—C11—C1	119.8 (3)
N1—N2—H2	116 (2)	N1—C11—H11	120.1
C2—O1—H1	109.5	C1—C11—H11	120.1
C2—C1—C10	119.2 (3)	O2—C12—N2	122.7 (3)
C2—C1—C11	120.7 (3)	O2—C12—C13	122.2 (3)
C10—C1—C11	120.2 (3)	N2—C12—C13	115.2 (3)
O1—C2—C1	123.0 (3)	C18—C13—C14	119.4 (3)
O1—C2—C3	116.2 (3)	C18—C13—C12	122.8 (3)
C1—C2—C3	120.8 (3)	C14—C13—C12	117.7 (3)
C4—C3—C2	120.7 (3)	C15—C14—C13	122.0 (3)
C4—C3—H3	119.7	C15—C14—H14	119.0
C2—C3—H3	119.7	C13—C14—H14	119.0
C3—C4—C5	121.2 (3)	C16—C15—C14	117.4 (3)
C3—C4—H4	119.4	C16—C15—C19	121.6 (3)
C5—C4—H4	119.4	C14—C15—C19	121.1 (3)
C4—C5—C6	121.7 (3)	C17—C16—C15	121.8 (3)
C4—C5—C10	119.1 (3)	C17—C16—H16	119.1
C6—C5—C10	119.2 (3)	C15—C16—H16	119.1
C7—C6—C5	121.4 (3)	C16—C17—C18	120.6 (3)
C7—C6—H6	119.3	C16—C17—H17	119.7
C5—C6—H6	119.3	C18—C17—H17	119.7
C6—C7—C8	119.8 (3)	C17—C18—C13	118.8 (3)
C6—C7—H7	120.1	C17—C18—H18	120.6
C8—C7—H7	120.1	C13—C18—H18	120.6
C9—C8—C7	120.9 (4)	C15—C19—H19A	109.5
C9—C8—H8	119.5	C15—C19—H19B	109.5
C7—C8—H8	119.5	H19A—C19—H19B	109.5
C8—C9—C10	121.3 (3)	C15—C19—H19C	109.5
C8—C9—H9	119.3	H19A—C19—H19C	109.5
C10—C9—H9	119.3	H19B—C19—H19C	109.5
C9—C10—C5	117.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (1)	2.00 (1)	2.869 (3)	163 (3)
O1—H1···N1	0.82	1.85	2.567 (3)	146

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₂O₂
M_r	304.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.1927 (11), 31.042 (4), 7.3557 (11)
β (°)	108.455 (2)
V (Å³)	1557.9 (4)
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	0.983, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	8247, 3295, 1736
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.166, 1.04
No. of reflections	3295
No. of parameters	214
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)	0.17, −0.20

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
N2—H2···O2ⁱ	0.898 (10)	2.000 (14)	2.869 (3)	163 (3)
O1—H1···N1	0.82	1.85	2.567 (3)	146

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Acknowledgements

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

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hillmer, A. S., Putcha, P., Levin, J., Hogen, T., Hyman, B. T., Kretzschmar, H., McLean, P. J. & Giese, A. (2010). Biochem. Biophys. Res. Commun. 391, 461–466. Web of Science CrossRef PubMed CAS Google Scholar
Liu, S.-Y. & Wang, X. (2010). Acta Cryst. E66, o1775. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, S.-Y. & You, Z. (2010). Acta Cryst. E66, o1652. Web of Science CSD CrossRef IUCr Journals Google Scholar
Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425–429. PubMed CAS Google Scholar
Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2898. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vijayakumar, S., Adhikari, A., Kalluraya, B. & Chandrasekharan, K. (2009). Opt. Mater. 31, 1564–1569. Web of Science CrossRef CAS Google Scholar
Xu, L., Huang, S.-S., Zhang, B.-J., Wang, S.-Y. & Zhang, H.-L. (2009). Acta Cryst. E65, o2412. Web of Science CSD CrossRef IUCr Journals Google Scholar