N′-(2-Hy­droxy-1-naphth­yl­methylidene)-3-meth­oxy­benzohydrazide

Hang, Z.-X.

doi:10.1107/S1600536810022026

organic compounds

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Volume 66| Part 7| July 2010| Page o1650

doi:10.1107/S1600536810022026

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N′-(2-Hydroxy-1-naphthylmethylidene)-3-methoxybenzohydrazide

Zhi-Xi Hang ^a ^*

^aCollege of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu 241000, People's Republic of China
^*Correspondence e-mail: hangzhx@163.com

(Received 1 June 2010; accepted 8 June 2010; online 16 June 2010)

In the title compound, C₁₉H₁₆N₂O₃, the dihedral angle between the naphthalene ring system and the benzene ring is 19.8 (3)°. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. In the crystal, molecules are linked via intermolecular N—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of hydrazone compounds, see: Arunkumar et al. (2006 ); Saxena et al. (2008 ); Zia-ur-Rehman et al. (2009 ); Galal et al. (2009 ); Bordoloi et al. (2009 ). For similar hydrazone compounds, see: Han et al. (2010 ); Wang et al. (2010 ); Qiao et al. (2010 ); Suleiman Gwaram et al. (2010 ); Sun et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₆N₂O₃
M_r = 320.34
Monoclinic, P 2₁ /n
a = 7.1700 (15) Å
b = 31.174 (7) Å
c = 7.4669 (16) Å
β = 109.746 (12)°
V = 1570.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.984, T_max = 0.984
9232 measured reflections
3405 independent reflections
1839 reflections with I > 2σ(I)
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.141
S = 0.92
3405 reflections
222 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.91 (1)	1.97 (1)	2.842 (3)	163 (2)
O1—H1⋯N1	0.82	1.85	2.574 (2)	146
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022026/rz2461sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022026/rz2461Isup2.hkl

checkCIF report

Comment top

Considerable interest has been focused on hydrazone compounds due to their excellent biological activities (Arunkumar et al., 2006; Saxena et al., 2008; Zia-ur-Rehman et al., 2009; Galal et al., 2009; Bordoloi et al., 2009). In the last few years, a great deal of hydrazone compounds have been prepared and characterized by X-ray diffraction (Han et al., 2010; Wang et al., 2010; Qiao et al., 2010; Suleiman Gwaram et al., 2010; Sun et al., 2009). The present paper reports a new hydrazone compound, N'-(2-hydroxynaphthylene)-3-methoxybenzohydrazide.

In the title compound (Fig. 1) the dihedral angle between the naphthalene ring system and the benzene ring is 19.8 (3)°. Bond lengths and angles are comparable to those found in similar hydrazone compounds cited above. An intramolecular O—H···N hydrogen bond (Table 1) stabilizes the molecular conformation. The molecules are linked via intermolecular N—H···O hydrogen bonds (Table 1), to form chains along the a axis (Fig. 2).

Related literature top

For the biological activity of hydrazone compounds, see: Arunkumar et al. (2006); Saxena et al. (2008); Zia-ur-Rehman et al. (2009); Galal et al. (2009); Bordoloi et al. (2009). For similar hydrazone compounds, see: Han et al. (2010); Wang et al. (2010); Qiao et al. (2010); Suleiman Gwaram et al. (2010); Sun et al. (2009).

Experimental top

Equimolar quantities (1 mmol) of 3-methoxybenzohydrazide and 2-hydroxy-1-naphthyaldehyde were mixed and stirred in methanol for 2 h at ambient temperature. The resulting mixture was concentrated under recuced pressure. The residue, purified by washing with cold methanol and diethyl ether, afforded the pure product of the hydrazone compound. Colourless single crystals suitable for X-ray diffraction were obtained on slow evaqporation of a methanol solution.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot of the title compound at the 30% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The intramolecular O–H···N hydrogen bond is drawn as a dashed line.
	Fig. 2. Packing diagram of the title compound viewed along the c axis. Intermolecular hydrogen bonds are shown as dashed lines.

N'-(2-Hydroxy-1-naphthylmethylidene)-3-methoxybenzohydrazide top

Crystal data top

C₁₉H₁₆N₂O₃	F(000) = 672
M_r = 320.34	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1460 reflections
a = 7.1700 (15) Å	θ = 2.5–24.0°
b = 31.174 (7) Å	µ = 0.09 mm⁻¹
c = 7.4669 (16) Å	T = 298 K
β = 109.746 (12)°	Block, colourless
V = 1570.9 (6) Å³	0.18 × 0.17 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3405 independent reflections
Radiation source: fine-focus sealed tube	1839 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ω scans	θ_max = 27.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.984, T_max = 0.984	k = −39→35
9232 measured reflections	l = −7→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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ²(F_o²) + (0.0597P)²] where P = (F_o² + 2F_c²)/3
3405 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O₃	V = 1570.9 (6) Å³
M_r = 320.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1700 (15) Å	µ = 0.09 mm⁻¹
b = 31.174 (7) Å	T = 298 K
c = 7.4669 (16) Å	0.18 × 0.17 × 0.17 mm
β = 109.746 (12)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3405 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1839 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.984	R_int = 0.093
9232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	Δρ_max = 0.22 e Å⁻³
3405 reflections	Δρ_min = −0.23 e Å⁻³
222 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.9564 (3)	0.21280 (5)	0.6283 (3)	0.0368 (5)
N2	0.9265 (3)	0.24056 (6)	0.4765 (3)	0.0377 (5)
O1	1.0227 (3)	0.19610 (5)	0.9820 (2)	0.0522 (5)
H1	1.0193	0.2108	0.8900	0.078*
O2	1.1086 (2)	0.29306 (4)	0.6668 (2)	0.0446 (4)
O3	0.8581 (3)	0.42263 (5)	0.2180 (3)	0.0610 (5)
C1	0.9067 (3)	0.14315 (6)	0.7351 (3)	0.0325 (5)
C2	0.9652 (3)	0.15572 (7)	0.9238 (3)	0.0374 (5)
C3	0.9684 (4)	0.12616 (8)	1.0675 (3)	0.0448 (6)
H3	1.0045	0.1353	1.1932	0.054*
C4	0.9194 (4)	0.08463 (8)	1.0244 (4)	0.0465 (6)
H4	0.9231	0.0656	1.1215	0.056*
C5	0.8625 (3)	0.06948 (7)	0.8351 (3)	0.0385 (6)
C6	0.8142 (4)	0.02588 (8)	0.7898 (4)	0.0512 (7)
H6	0.8181	0.0068	0.8867	0.061*
C7	0.7624 (4)	0.01126 (8)	0.6091 (5)	0.0632 (8)
H7	0.7330	−0.0176	0.5820	0.076*
C8	0.7539 (5)	0.04030 (8)	0.4638 (4)	0.0667 (8)
H8	0.7171	0.0305	0.3390	0.080*
C9	0.7981 (4)	0.08248 (8)	0.5010 (4)	0.0521 (7)
H9	0.7913	0.1009	0.4010	0.063*
C10	0.8543 (3)	0.09898 (7)	0.6881 (3)	0.0351 (5)
C11	0.8922 (3)	0.17435 (7)	0.5871 (3)	0.0358 (5)
H11	0.8354	0.1664	0.4601	0.043*
C12	1.0051 (3)	0.28023 (7)	0.5079 (3)	0.0330 (5)
C13	0.9564 (3)	0.30824 (7)	0.3373 (3)	0.0324 (5)
C14	0.9349 (3)	0.35181 (7)	0.3628 (3)	0.0363 (5)
H14	0.9528	0.3624	0.4839	0.044*
C15	0.8871 (3)	0.37955 (7)	0.2097 (4)	0.0417 (6)
C16	0.8640 (4)	0.36340 (9)	0.0300 (4)	0.0530 (7)
H16	0.8325	0.3819	−0.0736	0.064*
C17	0.8871 (4)	0.32039 (9)	0.0040 (4)	0.0535 (7)
H17	0.8726	0.3100	−0.1167	0.064*
C18	0.9320 (3)	0.29230 (7)	0.1567 (3)	0.0417 (6)
H18	0.9457	0.2631	0.1387	0.050*
C19	0.8793 (5)	0.44027 (8)	0.3982 (5)	0.0690 (9)
H19A	0.7877	0.4266	0.4486	0.104*
H19B	0.8525	0.4705	0.3853	0.104*
H19C	1.0122	0.4357	0.4830	0.104*
H2	0.836 (3)	0.2332 (9)	0.363 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0382 (11)	0.0332 (10)	0.0349 (11)	0.0007 (9)	0.0070 (9)	0.0046 (9)
N2	0.0449 (12)	0.0303 (10)	0.0301 (11)	−0.0025 (9)	0.0024 (9)	0.0034 (9)
O1	0.0689 (12)	0.0450 (10)	0.0397 (10)	−0.0084 (10)	0.0143 (10)	−0.0079 (8)
O2	0.0511 (10)	0.0396 (9)	0.0309 (9)	−0.0023 (8)	−0.0020 (8)	−0.0008 (7)
O3	0.0633 (13)	0.0403 (10)	0.0735 (14)	0.0055 (9)	0.0154 (11)	0.0180 (10)
C1	0.0297 (12)	0.0359 (12)	0.0311 (13)	0.0015 (10)	0.0091 (10)	0.0030 (10)
C2	0.0353 (13)	0.0369 (13)	0.0390 (14)	0.0017 (11)	0.0114 (11)	−0.0016 (11)
C3	0.0468 (15)	0.0558 (16)	0.0301 (13)	0.0031 (13)	0.0108 (12)	0.0026 (12)
C4	0.0460 (15)	0.0502 (15)	0.0443 (15)	0.0037 (13)	0.0167 (12)	0.0151 (13)
C5	0.0344 (13)	0.0353 (12)	0.0469 (15)	0.0032 (11)	0.0150 (11)	0.0058 (11)
C6	0.0495 (16)	0.0413 (14)	0.0623 (18)	0.0014 (13)	0.0184 (14)	0.0107 (14)
C7	0.071 (2)	0.0338 (14)	0.082 (2)	−0.0066 (13)	0.0229 (18)	−0.0013 (15)
C8	0.093 (2)	0.0472 (16)	0.0570 (19)	−0.0146 (16)	0.0211 (18)	−0.0146 (15)
C9	0.0714 (19)	0.0417 (14)	0.0436 (15)	−0.0093 (13)	0.0199 (14)	−0.0033 (12)
C10	0.0328 (12)	0.0344 (12)	0.0371 (13)	0.0016 (10)	0.0105 (11)	0.0010 (11)
C11	0.0370 (13)	0.0371 (12)	0.0296 (12)	0.0000 (11)	0.0065 (10)	−0.0002 (10)
C12	0.0326 (12)	0.0318 (12)	0.0305 (12)	0.0020 (10)	0.0054 (10)	−0.0011 (10)
C13	0.0285 (11)	0.0363 (12)	0.0282 (12)	−0.0034 (10)	0.0042 (9)	−0.0006 (10)
C14	0.0327 (12)	0.0370 (12)	0.0368 (13)	−0.0025 (10)	0.0084 (10)	−0.0009 (11)
C15	0.0333 (13)	0.0387 (13)	0.0481 (15)	−0.0008 (11)	0.0073 (11)	0.0112 (12)
C16	0.0485 (16)	0.0640 (18)	0.0408 (16)	−0.0083 (14)	0.0075 (12)	0.0168 (14)
C17	0.0556 (17)	0.0742 (19)	0.0307 (14)	−0.0132 (15)	0.0147 (12)	−0.0008 (14)
C18	0.0440 (14)	0.0447 (13)	0.0358 (14)	−0.0041 (12)	0.0126 (11)	−0.0034 (11)
C19	0.074 (2)	0.0426 (15)	0.100 (3)	0.0077 (15)	0.042 (2)	0.0013 (16)

Geometric parameters (Å, º) top

N1—C11	1.284 (3)	C7—C8	1.398 (4)
N1—N2	1.384 (2)	C7—H7	0.9300
N2—C12	1.346 (3)	C8—C9	1.359 (3)
N2—H2	0.905 (10)	C8—H8	0.9300
O1—C2	1.350 (2)	C9—C10	1.414 (3)
O1—H1	0.8200	C9—H9	0.9300
O2—C12	1.235 (3)	C11—H11	0.9300
O3—C15	1.364 (3)	C12—C13	1.485 (3)
O3—C19	1.413 (3)	C13—C14	1.387 (3)
C1—C2	1.384 (3)	C13—C18	1.391 (3)
C1—C10	1.439 (3)	C14—C15	1.381 (3)
C1—C11	1.450 (3)	C14—H14	0.9300
C2—C3	1.408 (3)	C15—C16	1.390 (3)
C3—C4	1.351 (3)	C16—C17	1.373 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.414 (3)	C17—C18	1.387 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.415 (3)	C18—H18	0.9300
C5—C10	1.418 (3)	C19—H19A	0.9600
C6—C7	1.351 (4)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600

C11—N1—N2	116.33 (18)	C9—C10—C5	116.9 (2)
C12—N2—N1	119.46 (18)	C9—C10—C1	123.6 (2)
C12—N2—H2	121.4 (18)	C5—C10—C1	119.5 (2)
N1—N2—H2	118.1 (18)	N1—C11—C1	121.1 (2)
C2—O1—H1	109.5	N1—C11—H11	119.5
C15—O3—C19	117.2 (2)	C1—C11—H11	119.5
C2—C1—C10	118.92 (19)	O2—C12—N2	123.04 (19)
C2—C1—C11	120.4 (2)	O2—C12—C13	121.64 (19)
C10—C1—C11	120.69 (19)	N2—C12—C13	115.32 (19)
O1—C2—C1	123.1 (2)	C14—C13—C18	120.0 (2)
O1—C2—C3	116.1 (2)	C14—C13—C12	117.57 (19)
C1—C2—C3	120.8 (2)	C18—C13—C12	122.48 (19)
C4—C3—C2	120.6 (2)	C15—C14—C13	120.5 (2)
C4—C3—H3	119.7	C15—C14—H14	119.7
C2—C3—H3	119.7	C13—C14—H14	119.7
C3—C4—C5	121.5 (2)	O3—C15—C14	125.3 (2)
C3—C4—H4	119.3	O3—C15—C16	115.5 (2)
C5—C4—H4	119.3	C14—C15—C16	119.2 (2)
C4—C5—C6	121.6 (2)	C17—C16—C15	120.6 (2)
C4—C5—C10	118.7 (2)	C17—C16—H16	119.7
C6—C5—C10	119.7 (2)	C15—C16—H16	119.7
C7—C6—C5	121.7 (2)	C16—C17—C18	120.4 (2)
C7—C6—H6	119.2	C16—C17—H17	119.8
C5—C6—H6	119.2	C18—C17—H17	119.8
C6—C7—C8	118.8 (2)	C17—C18—C13	119.3 (2)
C6—C7—H7	120.6	C17—C18—H18	120.4
C8—C7—H7	120.6	C13—C18—H18	120.4
C9—C8—C7	121.5 (3)	O3—C19—H19A	109.5
C9—C8—H8	119.3	O3—C19—H19B	109.5
C7—C8—H8	119.3	H19A—C19—H19B	109.5
C8—C9—C10	121.5 (2)	O3—C19—H19C	109.5
C8—C9—H9	119.2	H19A—C19—H19C	109.5
C10—C9—H9	119.2	H19B—C19—H19C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.91 (1)	1.97 (1)	2.842 (3)	163 (2)
O1—H1···N1	0.82	1.85	2.574 (2)	146

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₂O₃
M_r	320.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.1700 (15), 31.174 (7), 7.4669 (16)
β (°)	109.746 (12)
V (Å³)	1570.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.18 × 0.17 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.984, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9232, 3405, 1839
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.141, 0.92
No. of reflections	3405
No. of parameters	222
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)	0.22, −0.23

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
N2—H2···O2ⁱ	0.905 (10)	1.965 (13)	2.842 (3)	163 (2)
O1—H1···N1	0.82	1.85	2.574 (2)	146.1

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

Acknowledgements

The author acknowledges the Pivot Construction Subject of Applied Chemistry and the Teaching Group of the Courses Construction on Engineering Course Chemistry for financial support.

References

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