organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Tang, C.-B. (2006). Acta Cryst. E62, m2629-m2630.], 2007a[Tang, C.-B. (2007a). Acta Cryst. E63, m2654.],b[Tang, C.-B. (2007b). Acta Cryst. E63, m2785-m2786.],c[Tang, C.-B. (2007c). Acta Cryst. E63, o4545.],d[Tang, C.-B. (2007d). Acta Cryst. E63, o4841.]). For reference structural data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C19H16N2O3

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.971, Tmax = 0.972

  • 13232 measured reflections

  • 3550 independent reflections

  • 2161 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

H2 atom was located from a difference Fourier map and refined isotropically, with N—H distance restrained to 0.90 (1) Å. Other H atoms were constrained to ideal geometries, with C—H = 0.93–0.96 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C), 1.5Ueq(C19 and O1).

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
[Figure 1] Fig. 1. The molecular structure of the compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonds drawn as dashed lines.
N'-(2-Hydroxynaphthylidene)-4-methoxybenzohydrazide top
Crystal data top
C19H16N2O3F(000) = 672
Mr = 320.34Dx = 1.368 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1378 reflections
a = 11.159 (2) Åθ = 2.2–24.5°
b = 15.790 (3) ŵ = 0.09 mm1
c = 8.8300 (18) ÅT = 298 K
β = 91.70 (3)°Cut from a needle, colorless
V = 1555.2 (5) Å30.32 × 0.32 × 0.30 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3550 independent reflections
Radiation source: fine-focus sealed tube2161 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.971, Tmax = 0.972k = 2020
13232 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0391P)2 + 0.168P]
where P = (Fo2 + 2Fc2)/3
3550 reflections(Δ/σ)max = 0.001
222 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = 0.20 e Å3
Crystal data top
C19H16N2O3V = 1555.2 (5) Å3
Mr = 320.34Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.159 (2) ŵ = 0.09 mm1
b = 15.790 (3) ÅT = 298 K
c = 8.8300 (18) Å0.32 × 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)
Tmin = 0.971, Tmax = 0.972Rint = 0.052
13232 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0561 restraint
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.18 e Å3
3550 reflectionsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
O10.44682 (14)0.12307 (9)0.77419 (16)0.0569 (4)
H10.40890.15840.72440.085*
O20.24817 (13)0.32717 (8)0.67361 (14)0.0515 (4)
O30.02184 (13)0.57256 (9)0.17402 (17)0.0602 (5)
N10.30518 (14)0.17750 (9)0.55897 (17)0.0415 (4)
N20.25139 (15)0.24056 (10)0.47098 (17)0.0423 (4)
C10.35505 (16)0.03145 (12)0.5862 (2)0.0362 (4)
C20.42732 (17)0.04559 (13)0.7145 (2)0.0431 (5)
C30.48691 (18)0.02246 (15)0.7874 (2)0.0520 (6)
H30.53700.01210.87150.062*
C40.47221 (19)0.10234 (14)0.7367 (2)0.0526 (6)
H40.51240.14620.78680.063*
C50.39740 (17)0.12109 (13)0.6096 (2)0.0434 (5)
C60.3824 (2)0.20495 (13)0.5558 (3)0.0561 (6)
H60.42300.24890.60510.067*
C70.3101 (2)0.22238 (14)0.4342 (3)0.0608 (6)
H70.30070.27790.40070.073*
C80.2498 (2)0.15638 (14)0.3591 (3)0.0586 (6)
H80.20050.16830.27500.070*
C90.26197 (18)0.07449 (12)0.4075 (2)0.0458 (5)
H90.21980.03180.35660.055*
C100.33734 (16)0.05348 (11)0.5331 (2)0.0371 (5)
C110.29956 (17)0.10221 (12)0.5053 (2)0.0388 (5)
H110.25940.09260.41310.047*
C120.22727 (17)0.31534 (11)0.5375 (2)0.0376 (5)
C130.17287 (17)0.38188 (11)0.4404 (2)0.0365 (4)
C140.18459 (18)0.46552 (12)0.4857 (2)0.0454 (5)
H140.22590.47780.57610.054*
C150.13651 (19)0.53130 (12)0.4000 (2)0.0493 (5)
H150.14660.58710.43170.059*
C160.07353 (17)0.51333 (12)0.2674 (2)0.0427 (5)
C170.05869 (18)0.43022 (12)0.2214 (2)0.0453 (5)
H170.01470.41800.13290.054*
C180.10864 (17)0.36569 (12)0.3058 (2)0.0406 (5)
H180.09950.31010.27250.049*
C190.0515 (2)0.65852 (13)0.2009 (3)0.0685 (7)
H19A0.02240.67550.29740.103*
H19B0.01530.69310.12270.103*
H19C0.13700.66520.20070.103*
H20.251 (2)0.2301 (14)0.3703 (12)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0614 (11)0.0580 (10)0.0505 (10)0.0051 (8)0.0100 (8)0.0063 (8)
O20.0791 (11)0.0422 (8)0.0326 (8)0.0005 (7)0.0063 (7)0.0019 (6)
O30.0683 (11)0.0440 (9)0.0674 (11)0.0126 (7)0.0113 (8)0.0084 (8)
N10.0508 (11)0.0356 (9)0.0380 (9)0.0008 (8)0.0009 (8)0.0047 (7)
N20.0608 (11)0.0320 (9)0.0339 (9)0.0046 (8)0.0029 (9)0.0013 (7)
C10.0350 (10)0.0388 (11)0.0350 (11)0.0019 (8)0.0038 (8)0.0062 (8)
C20.0391 (11)0.0500 (13)0.0405 (12)0.0026 (10)0.0036 (9)0.0034 (10)
C30.0414 (12)0.0728 (16)0.0413 (13)0.0038 (11)0.0065 (10)0.0114 (11)
C40.0465 (13)0.0549 (14)0.0564 (14)0.0122 (10)0.0035 (11)0.0204 (11)
C50.0371 (11)0.0461 (12)0.0474 (12)0.0058 (9)0.0077 (9)0.0119 (10)
C60.0589 (15)0.0399 (13)0.0700 (16)0.0138 (11)0.0121 (12)0.0144 (11)
C70.0684 (16)0.0394 (13)0.0750 (17)0.0035 (11)0.0085 (14)0.0022 (12)
C80.0658 (16)0.0512 (14)0.0586 (15)0.0033 (11)0.0020 (12)0.0065 (11)
C90.0500 (13)0.0380 (11)0.0492 (13)0.0013 (9)0.0004 (10)0.0014 (9)
C100.0349 (11)0.0396 (11)0.0370 (11)0.0022 (9)0.0062 (9)0.0069 (9)
C110.0421 (12)0.0395 (11)0.0348 (11)0.0008 (9)0.0006 (9)0.0035 (9)
C120.0423 (11)0.0359 (11)0.0346 (11)0.0056 (8)0.0005 (9)0.0003 (8)
C130.0397 (11)0.0349 (10)0.0350 (11)0.0017 (8)0.0033 (8)0.0002 (8)
C140.0545 (13)0.0409 (12)0.0403 (12)0.0017 (10)0.0045 (10)0.0061 (9)
C150.0609 (14)0.0322 (11)0.0547 (14)0.0017 (10)0.0011 (11)0.0036 (10)
C160.0408 (11)0.0412 (12)0.0458 (12)0.0050 (9)0.0008 (9)0.0032 (9)
C170.0454 (13)0.0479 (13)0.0421 (12)0.0002 (10)0.0077 (10)0.0004 (10)
C180.0467 (12)0.0351 (11)0.0397 (11)0.0029 (9)0.0020 (9)0.0046 (9)
C190.0857 (19)0.0414 (13)0.0784 (18)0.0172 (12)0.0019 (14)0.0076 (12)
Geometric parameters (Å, º) top
O1—C21.347 (2)C7—C81.397 (3)
O1—H10.8200C7—H70.9300
O2—C121.231 (2)C8—C91.367 (3)
O3—C161.363 (2)C8—H80.9300
O3—C191.415 (2)C9—C101.411 (3)
N1—C111.281 (2)C9—H90.9300
N1—N21.388 (2)C11—H110.9300
N2—C121.350 (2)C12—C131.475 (3)
N2—H20.904 (9)C13—C141.385 (2)
C1—C21.389 (3)C13—C181.394 (3)
C1—C101.432 (2)C14—C151.384 (3)
C1—C111.455 (2)C14—H140.9300
C2—C31.409 (3)C15—C161.377 (3)
C3—C41.347 (3)C15—H150.9300
C3—H30.9300C16—C171.382 (3)
C4—C51.410 (3)C17—C181.371 (3)
C4—H40.9300C17—H170.9300
C5—C61.415 (3)C18—H180.9300
C5—C101.421 (3)C19—H19A0.9600
C6—C71.352 (3)C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C2—O1—H1109.5C9—C10—C5117.31 (18)
C16—O3—C19117.63 (17)C9—C10—C1123.40 (17)
C11—N1—N2116.28 (16)C5—C10—C1119.29 (18)
C12—N2—N1118.18 (15)N1—C11—C1121.04 (18)
C12—N2—H2126.4 (15)N1—C11—H11119.5
N1—N2—H2114.0 (15)C1—C11—H11119.5
C2—C1—C10119.24 (17)O2—C12—N2121.54 (17)
C2—C1—C11120.36 (18)O2—C12—C13121.46 (17)
C10—C1—C11120.39 (17)N2—C12—C13116.99 (16)
O1—C2—C1123.23 (18)C14—C13—C18117.57 (18)
O1—C2—C3116.45 (18)C14—C13—C12118.53 (17)
C1—C2—C3120.31 (19)C18—C13—C12123.89 (17)
C4—C3—C2120.7 (2)C15—C14—C13121.75 (19)
C4—C3—H3119.6C15—C14—H14119.1
C2—C3—H3119.6C13—C14—H14119.1
C3—C4—C5121.63 (19)C16—C15—C14119.34 (19)
C3—C4—H4119.2C16—C15—H15120.3
C5—C4—H4119.2C14—C15—H15120.3
C4—C5—C6121.66 (19)O3—C16—C15124.67 (18)
C4—C5—C10118.73 (19)O3—C16—C17115.39 (18)
C6—C5—C10119.6 (2)C15—C16—C17119.94 (18)
C7—C6—C5121.3 (2)C18—C17—C16120.17 (18)
C7—C6—H6119.4C18—C17—H17119.9
C5—C6—H6119.4C16—C17—H17119.9
C6—C7—C8119.5 (2)C17—C18—C13121.20 (18)
C6—C7—H7120.2C17—C18—H18119.4
C8—C7—H7120.2C13—C18—H18119.4
C9—C8—C7121.0 (2)O3—C19—H19A109.5
C9—C8—H8119.5O3—C19—H19B109.5
C7—C8—H8119.5H19A—C19—H19B109.5
C8—C9—C10121.29 (19)O3—C19—H19C109.5
C8—C9—H9119.4H19A—C19—H19C109.5
C10—C9—H9119.4H19B—C19—H19C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.582 (2)146
N2—H2···O2i0.90 (1)1.96 (1)2.834 (2)163 (2)
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC19H16N2O3
Mr320.34
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.159 (2), 15.790 (3), 8.8300 (18)
β (°) 91.70 (3)
V3)1555.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.32 × 0.32 × 0.30
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.971, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
13232, 3550, 2161
Rint0.052
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.136, 1.04
No. of reflections3550
No. of parameters222
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.582 (2)146.1
N2—H2···O2i0.904 (9)1.957 (12)2.834 (2)163 (2)
Symmetry code: (i) x, y+1/2, z1/2.
 

Acknowledgements

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

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTang, C.-B. (2006). Acta Cryst. E62, m2629–m2630.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationTang, C.-B. (2007a). Acta Cryst. E63, m2654.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationTang, C.-B. (2007b). Acta Cryst. E63, m2785–m2786.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationTang, C.-B. (2007c). Acta Cryst. E63, o4545.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationTang, C.-B. (2007d). Acta Cryst. E63, o4841.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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