N′-(2-Hydroxy­naphthyl­idene)-4-methoxy­benzo­hydrazide

Tang, C.-B.

doi:10.1107/S1600536808008076

organic compounds

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Volume 64| Part 4| April 2008| Page o768

doi:10.1107/S1600536808008076

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N′-(2-Hydroxynaphthylidene)-4-methoxybenzohydrazide

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: chunbao_tang@163.com

(Received 21 March 2008; accepted 25 March 2008; online 29 March 2008)

The title Schiff base compound, C₁₉H₁₆N₂O₃, was derived from the condensation reaction of 2-hydroxy-1-naphthylaldehyde with 4-methoxybenzohydrazide. The dihedral angle between the benzene ring and the naphthyl ring system is 6.8 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O intermolecular hydrogen bonds, forming chains running along the c axis.

Related literature

For related structures, see: Tang (2006 , 2007a ,b ,c ,d ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₆N₂O₃
M_r = 320.34
Monoclinic, P 2₁ /c
a = 11.159 (2) Å
b = 15.790 (3) Å
c = 8.8300 (18) Å
β = 91.70 (3)°
V = 1555.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.32 × 0.32 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.971, T_max = 0.972
13232 measured reflections
3550 independent reflections
2161 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.136
S = 1.04
3550 reflections
222 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 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
O1—H1⋯N1	0.82	1.86	2.582 (2)	146
N2—H2⋯O2ⁱ	0.904 (9)	1.957 (12)	2.834 (2)	163 (2)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536808008076/sj2478sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008076/sj2478Isup2.hkl

checkCIF report

Comment top

Recently, the author has reported the structures of several Schiff base compounds (Tang, 2006, 2007a,b,c,d) and, in continuation of work in this area, reports herein the structure of the title compound, (I), Fig. 1, a new Schiff base compound.

In the title compound (Fig. 1), the dihedral angle between the benzene ring and the naphtyl ring is 6.8 (2)°. The torsion angles C1—C11—N1—N2, C11—N1—N2—C12, and N1—N2—C12—C13 are 1.3 (2), 17.0 (2), and 1.5 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through N—H···O intermolecular hydrogen bonds (Table 1), forming chains running along the c axis (Fig. 2).

Related literature top

For related structures, see: Tang (2006, 2007a,b,c,d). For reference structural data, see: Allen et al. (1987).

Experimental top

2-Hydroxy-1-naphtylaldehyde (0.1 mmol, 17.2 mg) and 4-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were dissolved in an ethanol solution (20 ml). The mixture was stirred at reflux for 10 min to give a clear colorless solution. Colorless needle-like crystals of the compound were formed by slow evaporation of the solvent over several days.

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. The molecular structure of the compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonds drawn as dashed lines.

N'-(2-Hydroxynaphthylidene)-4-methoxybenzohydrazide top

Crystal data top

C₁₉H₁₆N₂O₃	F(000) = 672
M_r = 320.34	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1378 reflections
a = 11.159 (2) Å	θ = 2.2–24.5°
b = 15.790 (3) Å	µ = 0.09 mm⁻¹
c = 8.8300 (18) Å	T = 298 K
β = 91.70 (3)°	Cut from a needle, colorless
V = 1555.2 (5) Å³	0.32 × 0.32 × 0.30 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3550 independent reflections
Radiation source: fine-focus sealed tube	2161 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.971, T_max = 0.972	k = −20→20
13232 measured reflections	l = −11→11

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0391P)² + 0.168P] where P = (F_o² + 2F_c²)/3
3550 reflections	(Δ/σ)_max = 0.001
222 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O₃	V = 1555.2 (5) Å³
M_r = 320.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.159 (2) Å	µ = 0.09 mm⁻¹
b = 15.790 (3) Å	T = 298 K
c = 8.8300 (18) Å	0.32 × 0.32 × 0.30 mm
β = 91.70 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3550 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2161 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.972	R_int = 0.052
13232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	1 restraint
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.18 e Å⁻³
3550 reflections	Δρ_min = −0.20 e Å⁻³
222 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	0.44682 (14)	0.12307 (9)	0.77419 (16)	0.0569 (4)
H1	0.4089	0.1584	0.7244	0.085*
O2	0.24817 (13)	0.32717 (8)	0.67361 (14)	0.0515 (4)
O3	0.02184 (13)	0.57256 (9)	0.17402 (17)	0.0602 (5)
N1	0.30518 (14)	0.17750 (9)	0.55897 (17)	0.0415 (4)
N2	0.25139 (15)	0.24056 (10)	0.47098 (17)	0.0423 (4)
C1	0.35505 (16)	0.03145 (12)	0.5862 (2)	0.0362 (4)
C2	0.42732 (17)	0.04559 (13)	0.7145 (2)	0.0431 (5)
C3	0.48691 (18)	−0.02246 (15)	0.7874 (2)	0.0520 (6)
H3	0.5370	−0.0121	0.8715	0.062*
C4	0.47221 (19)	−0.10234 (14)	0.7367 (2)	0.0526 (6)
H4	0.5124	−0.1462	0.7868	0.063*
C5	0.39740 (17)	−0.12109 (13)	0.6096 (2)	0.0434 (5)
C6	0.3824 (2)	−0.20495 (13)	0.5558 (3)	0.0561 (6)
H6	0.4230	−0.2489	0.6051	0.067*
C7	0.3101 (2)	−0.22238 (14)	0.4342 (3)	0.0608 (6)
H7	0.3007	−0.2779	0.4007	0.073*
C8	0.2498 (2)	−0.15638 (14)	0.3591 (3)	0.0586 (6)
H8	0.2005	−0.1683	0.2750	0.070*
C9	0.26197 (18)	−0.07449 (12)	0.4075 (2)	0.0458 (5)
H9	0.2198	−0.0318	0.3566	0.055*
C10	0.33734 (16)	−0.05348 (11)	0.5331 (2)	0.0371 (5)
C11	0.29956 (17)	0.10221 (12)	0.5053 (2)	0.0388 (5)
H11	0.2594	0.0926	0.4131	0.047*
C12	0.22727 (17)	0.31534 (11)	0.5375 (2)	0.0376 (5)
C13	0.17287 (17)	0.38188 (11)	0.4404 (2)	0.0365 (4)
C14	0.18459 (18)	0.46552 (12)	0.4857 (2)	0.0454 (5)
H14	0.2259	0.4778	0.5761	0.054*
C15	0.13651 (19)	0.53130 (12)	0.4000 (2)	0.0493 (5)
H15	0.1466	0.5871	0.4317	0.059*
C16	0.07353 (17)	0.51333 (12)	0.2674 (2)	0.0427 (5)
C17	0.05869 (18)	0.43022 (12)	0.2214 (2)	0.0453 (5)
H17	0.0147	0.4180	0.1329	0.054*
C18	0.10864 (17)	0.36569 (12)	0.3058 (2)	0.0406 (5)
H18	0.0995	0.3101	0.2725	0.049*
C19	0.0515 (2)	0.65852 (13)	0.2009 (3)	0.0685 (7)
H19A	0.0224	0.6755	0.2974	0.103*
H19B	0.0153	0.6931	0.1227	0.103*
H19C	0.1370	0.6652	0.2007	0.103*
H2	0.251 (2)	0.2301 (14)	0.3703 (12)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0614 (11)	0.0580 (10)	0.0505 (10)	−0.0051 (8)	−0.0100 (8)	−0.0063 (8)
O2	0.0791 (11)	0.0422 (8)	0.0326 (8)	0.0005 (7)	−0.0063 (7)	−0.0019 (6)
O3	0.0683 (11)	0.0440 (9)	0.0674 (11)	0.0126 (7)	−0.0113 (8)	0.0084 (8)
N1	0.0508 (11)	0.0356 (9)	0.0380 (9)	0.0008 (8)	0.0009 (8)	0.0047 (7)
N2	0.0608 (11)	0.0320 (9)	0.0339 (9)	0.0046 (8)	−0.0029 (9)	0.0013 (7)
C1	0.0350 (10)	0.0388 (11)	0.0350 (11)	0.0019 (8)	0.0038 (8)	0.0062 (8)
C2	0.0391 (11)	0.0500 (13)	0.0405 (12)	−0.0026 (10)	0.0036 (9)	0.0034 (10)
C3	0.0414 (12)	0.0728 (16)	0.0413 (13)	0.0038 (11)	−0.0065 (10)	0.0114 (11)
C4	0.0465 (13)	0.0549 (14)	0.0564 (14)	0.0122 (10)	0.0035 (11)	0.0204 (11)
C5	0.0371 (11)	0.0461 (12)	0.0474 (12)	0.0058 (9)	0.0077 (9)	0.0119 (10)
C6	0.0589 (15)	0.0399 (13)	0.0700 (16)	0.0138 (11)	0.0121 (12)	0.0144 (11)
C7	0.0684 (16)	0.0394 (13)	0.0750 (17)	0.0035 (11)	0.0085 (14)	−0.0022 (12)
C8	0.0658 (16)	0.0512 (14)	0.0586 (15)	−0.0033 (11)	−0.0020 (12)	−0.0065 (11)
C9	0.0500 (13)	0.0380 (11)	0.0492 (13)	0.0013 (9)	−0.0004 (10)	0.0014 (9)
C10	0.0349 (11)	0.0396 (11)	0.0370 (11)	0.0022 (9)	0.0062 (9)	0.0069 (9)
C11	0.0421 (12)	0.0395 (11)	0.0348 (11)	−0.0008 (9)	0.0006 (9)	0.0035 (9)
C12	0.0423 (11)	0.0359 (11)	0.0346 (11)	−0.0056 (8)	0.0005 (9)	−0.0003 (8)
C13	0.0397 (11)	0.0349 (10)	0.0350 (11)	−0.0017 (8)	0.0033 (8)	−0.0002 (8)
C14	0.0545 (13)	0.0409 (12)	0.0403 (12)	−0.0017 (10)	−0.0045 (10)	−0.0061 (9)
C15	0.0609 (14)	0.0322 (11)	0.0547 (14)	0.0017 (10)	−0.0011 (11)	−0.0036 (10)
C16	0.0408 (11)	0.0412 (12)	0.0458 (12)	0.0050 (9)	−0.0008 (9)	0.0032 (9)
C17	0.0454 (13)	0.0479 (13)	0.0421 (12)	−0.0002 (10)	−0.0077 (10)	−0.0004 (10)
C18	0.0467 (12)	0.0351 (11)	0.0397 (11)	−0.0029 (9)	−0.0020 (9)	−0.0046 (9)
C19	0.0857 (19)	0.0414 (13)	0.0784 (18)	0.0172 (12)	0.0019 (14)	0.0076 (12)

Geometric parameters (Å, º) top

O1—C2	1.347 (2)	C7—C8	1.397 (3)
O1—H1	0.8200	C7—H7	0.9300
O2—C12	1.231 (2)	C8—C9	1.367 (3)
O3—C16	1.363 (2)	C8—H8	0.9300
O3—C19	1.415 (2)	C9—C10	1.411 (3)
N1—C11	1.281 (2)	C9—H9	0.9300
N1—N2	1.388 (2)	C11—H11	0.9300
N2—C12	1.350 (2)	C12—C13	1.475 (3)
N2—H2	0.904 (9)	C13—C14	1.385 (2)
C1—C2	1.389 (3)	C13—C18	1.394 (3)
C1—C10	1.432 (2)	C14—C15	1.384 (3)
C1—C11	1.455 (2)	C14—H14	0.9300
C2—C3	1.409 (3)	C15—C16	1.377 (3)
C3—C4	1.347 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.382 (3)
C4—C5	1.410 (3)	C17—C18	1.371 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.415 (3)	C18—H18	0.9300
C5—C10	1.421 (3)	C19—H19A	0.9600
C6—C7	1.352 (3)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600

C2—O1—H1	109.5	C9—C10—C5	117.31 (18)
C16—O3—C19	117.63 (17)	C9—C10—C1	123.40 (17)
C11—N1—N2	116.28 (16)	C5—C10—C1	119.29 (18)
C12—N2—N1	118.18 (15)	N1—C11—C1	121.04 (18)
C12—N2—H2	126.4 (15)	N1—C11—H11	119.5
N1—N2—H2	114.0 (15)	C1—C11—H11	119.5
C2—C1—C10	119.24 (17)	O2—C12—N2	121.54 (17)
C2—C1—C11	120.36 (18)	O2—C12—C13	121.46 (17)
C10—C1—C11	120.39 (17)	N2—C12—C13	116.99 (16)
O1—C2—C1	123.23 (18)	C14—C13—C18	117.57 (18)
O1—C2—C3	116.45 (18)	C14—C13—C12	118.53 (17)
C1—C2—C3	120.31 (19)	C18—C13—C12	123.89 (17)
C4—C3—C2	120.7 (2)	C15—C14—C13	121.75 (19)
C4—C3—H3	119.6	C15—C14—H14	119.1
C2—C3—H3	119.6	C13—C14—H14	119.1
C3—C4—C5	121.63 (19)	C16—C15—C14	119.34 (19)
C3—C4—H4	119.2	C16—C15—H15	120.3
C5—C4—H4	119.2	C14—C15—H15	120.3
C4—C5—C6	121.66 (19)	O3—C16—C15	124.67 (18)
C4—C5—C10	118.73 (19)	O3—C16—C17	115.39 (18)
C6—C5—C10	119.6 (2)	C15—C16—C17	119.94 (18)
C7—C6—C5	121.3 (2)	C18—C17—C16	120.17 (18)
C7—C6—H6	119.4	C18—C17—H17	119.9
C5—C6—H6	119.4	C16—C17—H17	119.9
C6—C7—C8	119.5 (2)	C17—C18—C13	121.20 (18)
C6—C7—H7	120.2	C17—C18—H18	119.4
C8—C7—H7	120.2	C13—C18—H18	119.4
C9—C8—C7	121.0 (2)	O3—C19—H19A	109.5
C9—C8—H8	119.5	O3—C19—H19B	109.5
C7—C8—H8	119.5	H19A—C19—H19B	109.5
C8—C9—C10	121.29 (19)	O3—C19—H19C	109.5
C8—C9—H9	119.4	H19A—C19—H19C	109.5
C10—C9—H9	119.4	H19B—C19—H19C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.582 (2)	146
N2—H2···O2ⁱ	0.90 (1)	1.96 (1)	2.834 (2)	163 (2)

Symmetry code: (i) x, −y+1/2, 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)	11.159 (2), 15.790 (3), 8.8300 (18)
β (°)	91.70 (3)
V (Å³)	1555.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.32 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.971, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	13232, 3550, 2161
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.136, 1.04
No. of reflections	3550
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)	0.18, −0.20

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
O1—H1···N1	0.82	1.86	2.582 (2)	146.1
N2—H2···O2ⁱ	0.904 (9)	1.957 (12)	2.834 (2)	163 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

Financial support from the Jiaying University Research Fund is gratefully acknowledged.

References

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