3-Hydr­oxy-N′-(2-methoxy­benzyl­idene)-2-naphthohydrazide

Hao, Y.-M.

doi:10.1107/S1600536809043086

organic compounds

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Volume 65| Part 12| December 2009| Page o2990

doi:10.1107/S1600536809043086

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3-Hydroxy-N′-(2-methoxybenzylidene)-2-naphthohydrazide

Yu-Mei Hao ^a ^*

^aDepartment of Chemistry, Baicheng Normal University, Baicheng 137000, People's Republic of China
^*Correspondence e-mail: jyxygzb@163.com

(Received 7 September 2009; accepted 19 October 2009; online 4 November 2009)

In the title Schiff base compound, C₁₉H₁₆N₂O₃, the dihedral angle between the mean planes of the benzene ring and the naphthyl ring system is 0.8 (2)°. The mean plane of the hydrazide group forms dihedral angles of 2.0 (2) and 2.2 (2)°, respectively, with the mean planes of the benzene ring and the naphthyl ring system. A strong intramolecular N—H⋯O hydrogen bond is present. In the crystal, intermolecular O—H⋯O hydrogen bonds form chains along the c axis and help to provide stability in the crystal packing.

Related literature

For the pharmaceutical and medicinal activities of Schiff bases, see: Dao et al. (2000 ); Sriram et al. (2006 ); Karthikeyan et al. (2006 ). For the coordination chemistry of Schiff bases, see: Ali et al. (2008 ); Kargar et al. (2009 ); Yeap et al. (2009 ). For the crystal structures of Schiff base compounds, see: Fun et al. (2009 ); Nadeem et al. (2009 ); Eltayeb et al. (2008 ); Hao (2009a ,b ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₆N₂O₃
M_r = 320.34
Monoclinic, P 2₁ /c
a = 7.4990 (6) Å
b = 15.4256 (13) Å
c = 13.3903 (12) Å
β = 96.709 (4)°
V = 1538.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 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 = 0.983, T_max = 0.984
9323 measured reflections
3349 independent reflections
2520 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.119
S = 1.04
3349 reflections
223 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.892 (9)	1.929 (14)	2.6613 (14)	138.3 (16)
O3—H3⋯O2ⁱ	0.82	1.86	2.6689 (13)	167
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043086/jj2010sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809043086/jj2010Isup2.hkl

checkCIF report

Comment top

Schiff base compounds, important to the pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006), have been used as versatile ligands in a variety of coordination chemistry applications (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). A number of contributions to these areas have been recently reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). With our continued interest in the structural chararcterization of these compounds (Hao, 2009a,b) the title compound, C₁₉H₁₆N₂O₃, (I), is reported.

In the title compound,(I), the mean plane of the hydrazide group, O2/C9/N2/N1/C8, forms dihedral angles of 2.0 (2) and 2.2 (2)°, with the mean planes of the benzene (C1–C6) and naphthyl rings (C10–C19), respectively (Fig. 1). The dihedral angle between the mean planes of the benzene and naphthyl rings is 0.9 (2)°, indicating the planarity of the molecule. All the bond lengths and angles are within normal values (Allen et al., 1987). Crystal packing is enhanced by strong intramolecular N—H···O and intermolecular O—H···O hydrogen bonds (Table 1), forming infinite one-dimensional chains running along the c axis of the unit cell (Fig. 2).

Related literature top

For the pharmaceutical and medicinal activities of Schiff bases, see: Dao et al. (2000); Sriram et al. (2006); Karthikeyan et al. (2006). For the coordination chemistry of Schiff bases, see: Ali et al. (2008); Kargar et al. (2009); Yeap et al. (2009). For the crystal structures of Schiff base compounds, see: Fun et al. (2009); Nadeem et al. (2009); Eltayeb et al. (2008); Hao (2009a,b). For bond-length data, see: Allen et al. (1987).

Experimental top

2-Methoxybenzaldehyde (0.1 mmol, 13.6 mg) and 3-hydroxy-2-naphthohydrazide (0.1 mmol) were refluxed in a 30 ml methanol solution for 30 min to give a clear colorless solution. Colorless block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.

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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids. A strong intramolecular N—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. Molecular packing of the title compound. Strong intramolecular N—H···O and intermolecular O—H···O hydrogen bonds (shown as dashed lines) form chains of molecules along the c axis of the unit cell help to provide stability in crystal packing. .

3-Hydroxy-N'-(2-methoxybenzylidene)-2-naphthohydrazide top

Crystal data top

C₁₉H₁₆N₂O₃	F(000) = 672
M_r = 320.34	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3028 reflections
a = 7.4990 (6) Å	θ = 2.6–30.0°
b = 15.4256 (13) Å	µ = 0.10 mm⁻¹
c = 13.3903 (12) Å	T = 298 K
β = 96.709 (4)°	Block, yellow
V = 1538.3 (2) Å³	0.18 × 0.17 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3349 independent reflections
Radiation source: fine-focus sealed tube	2520 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.983, T_max = 0.984	k = −19→19
9323 measured reflections	l = −17→14

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0572P)² + 0.2454P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3349 reflections	Δρ_max = 0.20 e Å⁻³
223 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0080 (13)

Crystal data top

C₁₉H₁₆N₂O₃	V = 1538.3 (2) Å³
M_r = 320.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4990 (6) Å	µ = 0.10 mm⁻¹
b = 15.4256 (13) Å	T = 298 K
c = 13.3903 (12) Å	0.18 × 0.17 × 0.17 mm
β = 96.709 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3349 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2520 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.984	R_int = 0.023
9323 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.20 e Å⁻³
3349 reflections	Δρ_min = −0.16 e Å⁻³
223 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 > 2σ(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	0.12815 (15)	1.07729 (7)	0.87156 (7)	0.0541 (3)
O2	0.53258 (17)	0.75013 (6)	1.13388 (7)	0.0558 (3)
O3	0.43652 (16)	0.74188 (7)	0.81939 (7)	0.0526 (3)
H3	0.4525	0.7391	0.7599	0.079*
N1	0.36704 (15)	0.89208 (7)	1.04707 (8)	0.0409 (3)
N2	0.41657 (16)	0.82106 (7)	0.99432 (8)	0.0408 (3)
C1	0.23017 (18)	1.03244 (9)	1.03531 (10)	0.0394 (3)
C2	0.14420 (18)	1.09540 (9)	0.97151 (10)	0.0399 (3)
C3	0.0791 (2)	1.17049 (10)	1.01086 (12)	0.0502 (4)
H3A	0.0221	1.2122	0.9682	0.060*
C4	0.0989 (3)	1.18316 (11)	1.11277 (13)	0.0663 (5)
H4	0.0542	1.2334	1.1391	0.080*
C5	0.1840 (3)	1.12260 (12)	1.17626 (12)	0.0731 (6)
H5	0.1976	1.1321	1.2453	0.088*
C6	0.2491 (2)	1.04788 (10)	1.13819 (11)	0.0553 (4)
H6	0.3067	1.0071	1.1818	0.066*
C7	0.0339 (3)	1.13737 (12)	0.80462 (11)	0.0631 (5)
H7A	−0.0867	1.1436	0.8210	0.095*
H7B	0.0313	1.1166	0.7369	0.095*
H7C	0.0934	1.1925	0.8107	0.095*
C8	0.29350 (19)	0.95271 (9)	0.99292 (10)	0.0422 (3)
H8	0.2795	0.9460	0.9234	0.051*
C9	0.49987 (18)	0.75329 (8)	1.04213 (9)	0.0371 (3)
C10	0.55517 (17)	0.68060 (8)	0.97827 (9)	0.0348 (3)
C11	0.52607 (18)	0.67543 (9)	0.87108 (9)	0.0381 (3)
C12	0.5848 (2)	0.60516 (9)	0.82249 (10)	0.0439 (3)
H12	0.5655	0.6030	0.7526	0.053*
C13	0.67397 (19)	0.53573 (9)	0.87531 (10)	0.0410 (3)
C14	0.7369 (2)	0.46152 (10)	0.82747 (12)	0.0561 (4)
H14	0.7206	0.4577	0.7577	0.067*
C15	0.8204 (2)	0.39614 (10)	0.88198 (14)	0.0615 (5)
H15	0.8599	0.3480	0.8490	0.074*
C16	0.8481 (2)	0.39985 (10)	0.98705 (13)	0.0558 (4)
H16	0.9060	0.3546	1.0235	0.067*
C17	0.79016 (19)	0.46984 (9)	1.03570 (11)	0.0459 (3)
H17	0.8084	0.4720	1.1056	0.055*
C18	0.70267 (17)	0.53921 (8)	0.98165 (10)	0.0370 (3)
C19	0.64040 (17)	0.61253 (9)	1.02959 (9)	0.0376 (3)
H19	0.6579	0.6150	1.0994	0.045*
H2	0.398 (2)	0.8200 (12)	0.9273 (7)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0763 (8)	0.0503 (6)	0.0362 (5)	0.0137 (5)	0.0089 (5)	0.0025 (4)
O2	0.0943 (9)	0.0461 (6)	0.0267 (5)	0.0082 (5)	0.0067 (5)	−0.0025 (4)
O3	0.0792 (8)	0.0541 (6)	0.0249 (5)	0.0150 (5)	0.0074 (5)	0.0044 (4)
N1	0.0482 (7)	0.0378 (6)	0.0375 (6)	−0.0002 (5)	0.0085 (5)	−0.0037 (5)
N2	0.0546 (7)	0.0381 (6)	0.0302 (6)	0.0043 (5)	0.0072 (5)	−0.0025 (5)
C1	0.0418 (7)	0.0381 (7)	0.0388 (7)	−0.0053 (6)	0.0063 (6)	−0.0028 (6)
C2	0.0435 (8)	0.0392 (7)	0.0375 (7)	−0.0052 (6)	0.0059 (6)	−0.0016 (6)
C3	0.0600 (9)	0.0390 (8)	0.0502 (8)	0.0048 (7)	0.0007 (7)	−0.0027 (6)
C4	0.0891 (13)	0.0515 (10)	0.0554 (10)	0.0164 (9)	−0.0042 (9)	−0.0200 (8)
C5	0.1083 (15)	0.0666 (12)	0.0402 (9)	0.0207 (11)	−0.0087 (9)	−0.0189 (8)
C6	0.0726 (11)	0.0507 (9)	0.0398 (8)	0.0091 (8)	−0.0047 (7)	−0.0034 (7)
C7	0.0817 (12)	0.0653 (11)	0.0412 (8)	0.0150 (9)	0.0030 (8)	0.0094 (8)
C8	0.0514 (8)	0.0423 (8)	0.0338 (7)	0.0004 (6)	0.0087 (6)	0.0007 (6)
C9	0.0471 (8)	0.0370 (7)	0.0279 (6)	−0.0065 (6)	0.0071 (5)	−0.0007 (5)
C10	0.0398 (7)	0.0376 (7)	0.0274 (6)	−0.0055 (5)	0.0060 (5)	−0.0005 (5)
C11	0.0457 (8)	0.0412 (7)	0.0279 (6)	−0.0021 (6)	0.0063 (5)	0.0036 (5)
C12	0.0595 (9)	0.0474 (8)	0.0261 (6)	−0.0037 (7)	0.0102 (6)	−0.0022 (6)
C13	0.0468 (8)	0.0398 (7)	0.0385 (7)	−0.0054 (6)	0.0137 (6)	−0.0024 (6)
C14	0.0767 (11)	0.0485 (9)	0.0469 (9)	−0.0011 (8)	0.0237 (8)	−0.0075 (7)
C15	0.0700 (11)	0.0409 (9)	0.0788 (12)	0.0036 (8)	0.0303 (9)	−0.0059 (8)
C16	0.0529 (9)	0.0421 (9)	0.0737 (11)	0.0035 (7)	0.0128 (8)	0.0066 (8)
C17	0.0446 (8)	0.0430 (8)	0.0498 (8)	−0.0024 (6)	0.0039 (6)	0.0051 (6)
C18	0.0362 (7)	0.0372 (7)	0.0381 (7)	−0.0056 (5)	0.0068 (5)	0.0009 (5)
C19	0.0427 (7)	0.0415 (7)	0.0280 (6)	−0.0058 (6)	0.0023 (5)	0.0003 (5)

Geometric parameters (Å, º) top

O1—C2	1.3587 (16)	C7—H7B	0.9600
O1—C7	1.4190 (18)	C7—H7C	0.9600
O2—C9	1.2253 (15)	C8—H8	0.9300
O3—C11	1.3683 (16)	C9—C10	1.4978 (18)
O3—H3	0.8200	C10—C19	1.3713 (18)
N1—C8	1.2693 (17)	C10—C11	1.4287 (17)
N1—N2	1.3778 (15)	C11—C12	1.3635 (19)
N2—C9	1.3415 (17)	C12—C13	1.409 (2)
N2—H2	0.892 (9)	C12—H12	0.9300
C1—C6	1.3889 (19)	C13—C18	1.4160 (18)
C1—C2	1.4000 (19)	C13—C14	1.419 (2)
C1—C8	1.4571 (19)	C14—C15	1.355 (2)
C2—C3	1.385 (2)	C14—H14	0.9300
C3—C4	1.369 (2)	C15—C16	1.399 (2)
C3—H3A	0.9300	C15—H15	0.9300
C4—C5	1.369 (2)	C16—C17	1.358 (2)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.373 (2)	C17—C18	1.4101 (19)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.4069 (19)
C7—H7A	0.9600	C19—H19	0.9300

C2—O1—C7	117.92 (11)	O2—C9—N2	122.48 (12)
C11—O3—H3	109.5	O2—C9—C10	120.42 (12)
C8—N1—N2	114.72 (11)	N2—C9—C10	117.10 (11)
C9—N2—N1	120.89 (11)	C19—C10—C11	117.92 (12)
C9—N2—H2	118.3 (12)	C19—C10—C9	115.53 (11)
N1—N2—H2	120.7 (12)	C11—C10—C9	126.54 (12)
C6—C1—C2	118.21 (13)	C12—C11—O3	121.40 (11)
C6—C1—C8	122.06 (13)	C12—C11—C10	120.25 (12)
C2—C1—C8	119.71 (12)	O3—C11—C10	118.34 (11)
O1—C2—C3	123.52 (13)	C11—C12—C13	121.71 (12)
O1—C2—C1	116.10 (12)	C11—C12—H12	119.1
C3—C2—C1	120.38 (13)	C13—C12—H12	119.1
C4—C3—C2	119.77 (14)	C12—C13—C18	118.92 (12)
C4—C3—H3A	120.1	C12—C13—C14	123.37 (13)
C2—C3—H3A	120.1	C18—C13—C14	117.71 (13)
C3—C4—C5	120.65 (15)	C15—C14—C13	120.96 (15)
C3—C4—H4	119.7	C15—C14—H14	119.5
C5—C4—H4	119.7	C13—C14—H14	119.5
C4—C5—C6	120.15 (15)	C14—C15—C16	121.09 (15)
C4—C5—H5	119.9	C14—C15—H15	119.5
C6—C5—H5	119.9	C16—C15—H15	119.5
C5—C6—C1	120.84 (15)	C17—C16—C15	119.77 (15)
C5—C6—H6	119.6	C17—C16—H16	120.1
C1—C6—H6	119.6	C15—C16—H16	120.1
O1—C7—H7A	109.5	C16—C17—C18	120.85 (14)
O1—C7—H7B	109.5	C16—C17—H17	119.6
H7A—C7—H7B	109.5	C18—C17—H17	119.6
O1—C7—H7C	109.5	C19—C18—C17	122.36 (12)
H7A—C7—H7C	109.5	C19—C18—C13	118.02 (12)
H7B—C7—H7C	109.5	C17—C18—C13	119.62 (12)
N1—C8—C1	122.61 (12)	C10—C19—C18	123.16 (12)
N1—C8—H8	118.7	C10—C19—H19	118.4
C1—C8—H8	118.7	C18—C19—H19	118.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.89 (1)	1.93 (1)	2.6613 (14)	138 (2)
O3—H3···O2ⁱ	0.82	1.86	2.6689 (13)	167

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₂O₃
M_r	320.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.4990 (6), 15.4256 (13), 13.3903 (12)
β (°)	96.709 (4)
V (Å³)	1538.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
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	0.983, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9323, 3349, 2520
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.119, 1.04
No. of reflections	3349
No. of parameters	223
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)	0.20, −0.16

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···O3	0.892 (9)	1.929 (14)	2.6613 (14)	138.3 (16)
O3—H3···O2ⁱ	0.82	1.86	2.6689 (13)	166.8

Symmetry code: (i) x, −y+3/2, z−1/2.

References

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Volume 65| Part 12| December 2009| Page o2990

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