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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o2990.
Published online 2009 November 4. doi:  10.1107/S1600536809043086
PMCID: PMC2971856

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

Abstract

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

An external file that holds a picture, illustration, etc.
Object name is e-65-o2990-scheme1.jpg

Experimental

Crystal data

  • C19H16N2O3
  • M r = 320.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2990-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.119
  • S = 1.04
  • 3349 reflections
  • 223 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

H2 was located from a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1)Å, and with Uiso restrained to 0.08Å2. Other H atoms were constrained to ideal geometries, with d(C—H) = 0.93-0.96 Å, d(O—H) = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O3 and C7).

Figures

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 ...

Crystal data

C19H16N2O3F(000) = 672
Mr = 320.34Dx = 1.383 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3028 reflections
a = 7.4990 (6) Åθ = 2.6–30.0°
b = 15.4256 (13) ŵ = 0.10 mm1
c = 13.3903 (12) ÅT = 298 K
β = 96.709 (4)°Block, yellow
V = 1538.3 (2) Å30.18 × 0.17 × 0.17 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3349 independent reflections
Radiation source: fine-focus sealed tube2520 reflections with I > 2σ(I)
graphiteRint = 0.023
ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.983, Tmax = 0.984k = −19→19
9323 measured reflectionsl = −17→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119w = 1/[σ2(Fo2) + (0.0572P)2 + 0.2454P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3349 reflectionsΔρmax = 0.20 e Å3
223 parametersΔρmin = −0.16 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0080 (13)

Special details

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)

xyzUiso*/Ueq
O10.12815 (15)1.07729 (7)0.87156 (7)0.0541 (3)
O20.53258 (17)0.75013 (6)1.13388 (7)0.0558 (3)
O30.43652 (16)0.74188 (7)0.81939 (7)0.0526 (3)
H30.45250.73910.75990.079*
N10.36704 (15)0.89208 (7)1.04707 (8)0.0409 (3)
N20.41657 (16)0.82106 (7)0.99432 (8)0.0408 (3)
C10.23017 (18)1.03244 (9)1.03531 (10)0.0394 (3)
C20.14420 (18)1.09540 (9)0.97151 (10)0.0399 (3)
C30.0791 (2)1.17049 (10)1.01086 (12)0.0502 (4)
H3A0.02211.21220.96820.060*
C40.0989 (3)1.18316 (11)1.11277 (13)0.0663 (5)
H40.05421.23341.13910.080*
C50.1840 (3)1.12260 (12)1.17626 (12)0.0731 (6)
H50.19761.13211.24530.088*
C60.2491 (2)1.04788 (10)1.13819 (11)0.0553 (4)
H60.30671.00711.18180.066*
C70.0339 (3)1.13737 (12)0.80462 (11)0.0631 (5)
H7A−0.08671.14360.82100.095*
H7B0.03131.11660.73690.095*
H7C0.09341.19250.81070.095*
C80.29350 (19)0.95271 (9)0.99292 (10)0.0422 (3)
H80.27950.94600.92340.051*
C90.49987 (18)0.75329 (8)1.04213 (9)0.0371 (3)
C100.55517 (17)0.68060 (8)0.97827 (9)0.0348 (3)
C110.52607 (18)0.67543 (9)0.87108 (9)0.0381 (3)
C120.5848 (2)0.60516 (9)0.82249 (10)0.0439 (3)
H120.56550.60300.75260.053*
C130.67397 (19)0.53573 (9)0.87531 (10)0.0410 (3)
C140.7369 (2)0.46152 (10)0.82747 (12)0.0561 (4)
H140.72060.45770.75770.067*
C150.8204 (2)0.39614 (10)0.88198 (14)0.0615 (5)
H150.85990.34800.84900.074*
C160.8481 (2)0.39985 (10)0.98705 (13)0.0558 (4)
H160.90600.35461.02350.067*
C170.79016 (19)0.46984 (9)1.03570 (11)0.0459 (3)
H170.80840.47201.10560.055*
C180.70267 (17)0.53921 (8)0.98165 (10)0.0370 (3)
C190.64040 (17)0.61253 (9)1.02959 (9)0.0376 (3)
H190.65790.61501.09940.045*
H20.398 (2)0.8200 (12)0.9273 (7)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0763 (8)0.0503 (6)0.0362 (5)0.0137 (5)0.0089 (5)0.0025 (4)
O20.0943 (9)0.0461 (6)0.0267 (5)0.0082 (5)0.0067 (5)−0.0025 (4)
O30.0792 (8)0.0541 (6)0.0249 (5)0.0150 (5)0.0074 (5)0.0044 (4)
N10.0482 (7)0.0378 (6)0.0375 (6)−0.0002 (5)0.0085 (5)−0.0037 (5)
N20.0546 (7)0.0381 (6)0.0302 (6)0.0043 (5)0.0072 (5)−0.0025 (5)
C10.0418 (7)0.0381 (7)0.0388 (7)−0.0053 (6)0.0063 (6)−0.0028 (6)
C20.0435 (8)0.0392 (7)0.0375 (7)−0.0052 (6)0.0059 (6)−0.0016 (6)
C30.0600 (9)0.0390 (8)0.0502 (8)0.0048 (7)0.0007 (7)−0.0027 (6)
C40.0891 (13)0.0515 (10)0.0554 (10)0.0164 (9)−0.0042 (9)−0.0200 (8)
C50.1083 (15)0.0666 (12)0.0402 (9)0.0207 (11)−0.0087 (9)−0.0189 (8)
C60.0726 (11)0.0507 (9)0.0398 (8)0.0091 (8)−0.0047 (7)−0.0034 (7)
C70.0817 (12)0.0653 (11)0.0412 (8)0.0150 (9)0.0030 (8)0.0094 (8)
C80.0514 (8)0.0423 (8)0.0338 (7)0.0004 (6)0.0087 (6)0.0007 (6)
C90.0471 (8)0.0370 (7)0.0279 (6)−0.0065 (6)0.0071 (5)−0.0007 (5)
C100.0398 (7)0.0376 (7)0.0274 (6)−0.0055 (5)0.0060 (5)−0.0005 (5)
C110.0457 (8)0.0412 (7)0.0279 (6)−0.0021 (6)0.0063 (5)0.0036 (5)
C120.0595 (9)0.0474 (8)0.0261 (6)−0.0037 (7)0.0102 (6)−0.0022 (6)
C130.0468 (8)0.0398 (7)0.0385 (7)−0.0054 (6)0.0137 (6)−0.0024 (6)
C140.0767 (11)0.0485 (9)0.0469 (9)−0.0011 (8)0.0237 (8)−0.0075 (7)
C150.0700 (11)0.0409 (9)0.0788 (12)0.0036 (8)0.0303 (9)−0.0059 (8)
C160.0529 (9)0.0421 (9)0.0737 (11)0.0035 (7)0.0128 (8)0.0066 (8)
C170.0446 (8)0.0430 (8)0.0498 (8)−0.0024 (6)0.0039 (6)0.0051 (6)
C180.0362 (7)0.0372 (7)0.0381 (7)−0.0056 (5)0.0068 (5)0.0009 (5)
C190.0427 (7)0.0415 (7)0.0280 (6)−0.0058 (6)0.0023 (5)0.0003 (5)

Geometric parameters (Å, °)

O1—C21.3587 (16)C7—H7B0.9600
O1—C71.4190 (18)C7—H7C0.9600
O2—C91.2253 (15)C8—H80.9300
O3—C111.3683 (16)C9—C101.4978 (18)
O3—H30.8200C10—C191.3713 (18)
N1—C81.2693 (17)C10—C111.4287 (17)
N1—N21.3778 (15)C11—C121.3635 (19)
N2—C91.3415 (17)C12—C131.409 (2)
N2—H20.892 (9)C12—H120.9300
C1—C61.3889 (19)C13—C181.4160 (18)
C1—C21.4000 (19)C13—C141.419 (2)
C1—C81.4571 (19)C14—C151.355 (2)
C2—C31.385 (2)C14—H140.9300
C3—C41.369 (2)C15—C161.399 (2)
C3—H3A0.9300C15—H150.9300
C4—C51.369 (2)C16—C171.358 (2)
C4—H40.9300C16—H160.9300
C5—C61.373 (2)C17—C181.4101 (19)
C5—H50.9300C17—H170.9300
C6—H60.9300C18—C191.4069 (19)
C7—H7A0.9600C19—H190.9300
C2—O1—C7117.92 (11)O2—C9—N2122.48 (12)
C11—O3—H3109.5O2—C9—C10120.42 (12)
C8—N1—N2114.72 (11)N2—C9—C10117.10 (11)
C9—N2—N1120.89 (11)C19—C10—C11117.92 (12)
C9—N2—H2118.3 (12)C19—C10—C9115.53 (11)
N1—N2—H2120.7 (12)C11—C10—C9126.54 (12)
C6—C1—C2118.21 (13)C12—C11—O3121.40 (11)
C6—C1—C8122.06 (13)C12—C11—C10120.25 (12)
C2—C1—C8119.71 (12)O3—C11—C10118.34 (11)
O1—C2—C3123.52 (13)C11—C12—C13121.71 (12)
O1—C2—C1116.10 (12)C11—C12—H12119.1
C3—C2—C1120.38 (13)C13—C12—H12119.1
C4—C3—C2119.77 (14)C12—C13—C18118.92 (12)
C4—C3—H3A120.1C12—C13—C14123.37 (13)
C2—C3—H3A120.1C18—C13—C14117.71 (13)
C3—C4—C5120.65 (15)C15—C14—C13120.96 (15)
C3—C4—H4119.7C15—C14—H14119.5
C5—C4—H4119.7C13—C14—H14119.5
C4—C5—C6120.15 (15)C14—C15—C16121.09 (15)
C4—C5—H5119.9C14—C15—H15119.5
C6—C5—H5119.9C16—C15—H15119.5
C5—C6—C1120.84 (15)C17—C16—C15119.77 (15)
C5—C6—H6119.6C17—C16—H16120.1
C1—C6—H6119.6C15—C16—H16120.1
O1—C7—H7A109.5C16—C17—C18120.85 (14)
O1—C7—H7B109.5C16—C17—H17119.6
H7A—C7—H7B109.5C18—C17—H17119.6
O1—C7—H7C109.5C19—C18—C17122.36 (12)
H7A—C7—H7C109.5C19—C18—C13118.02 (12)
H7B—C7—H7C109.5C17—C18—C13119.62 (12)
N1—C8—C1122.61 (12)C10—C19—C18123.16 (12)
N1—C8—H8118.7C10—C19—H19118.4
C1—C8—H8118.7C18—C19—H19118.4

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O30.89 (1)1.93 (1)2.6613 (14)138 (2)
O3—H3···O2i0.821.862.6689 (13)167

Symmetry codes: (i) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2010).

References

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