PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1650.
Published online 2010 June 16. doi:  10.1107/S1600536810022026
PMCID: PMC3006874

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

Abstract

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 [triangle]); Saxena et al. (2008 [triangle]); Zia-ur-Rehman et al. (2009 [triangle]); Galal et al. (2009 [triangle]); Bordoloi et al. (2009 [triangle]). For similar hydrazone compounds, see: Han et al. (2010 [triangle]); Wang et al. (2010 [triangle]); Qiao et al. (2010 [triangle]); Suleiman Gwaram et al. (2010 [triangle]); Sun et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1650-scheme1.jpg

Experimental

Crystal data

  • C19H16N2O3
  • M r = 320.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1650-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.141
  • S = 0.92
  • 3405 reflections
  • 222 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.23 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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

The H2 atom was found from a difference Fourier map and refined with an isotropic displacement parameter of 0.08 Å2, and with the N–H distance restrained to 0.90 (1) Å. The remaining H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 and 0.96 Å, O–H = 0.82 Å, and Uiso(H) = 1.2 or 1.5Ueq(C, O).

Figures

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.

Crystal data

C19H16N2O3F(000) = 672
Mr = 320.34Dx = 1.355 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1460 reflections
a = 7.1700 (15) Åθ = 2.5–24.0°
b = 31.174 (7) ŵ = 0.09 mm1
c = 7.4669 (16) ÅT = 298 K
β = 109.746 (12)°Block, colourless
V = 1570.9 (6) Å30.18 × 0.17 × 0.17 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3405 independent reflections
Radiation source: fine-focus sealed tube1839 reflections with I > 2σ(I)
graphiteRint = 0.093
ω scansθmax = 27.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.984, Tmax = 0.984k = −39→35
9232 measured reflectionsl = −7→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 0.92w = 1/[σ2(Fo2) + (0.0597P)2] where P = (Fo2 + 2Fc2)/3
3405 reflections(Δ/σ)max < 0.001
222 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = −0.23 e Å3

Special details

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)

xyzUiso*/Ueq
N10.9564 (3)0.21280 (5)0.6283 (3)0.0368 (5)
N20.9265 (3)0.24056 (6)0.4765 (3)0.0377 (5)
O11.0227 (3)0.19610 (5)0.9820 (2)0.0522 (5)
H11.01930.21080.89000.078*
O21.1086 (2)0.29306 (4)0.6668 (2)0.0446 (4)
O30.8581 (3)0.42263 (5)0.2180 (3)0.0610 (5)
C10.9067 (3)0.14315 (6)0.7351 (3)0.0325 (5)
C20.9652 (3)0.15572 (7)0.9238 (3)0.0374 (5)
C30.9684 (4)0.12616 (8)1.0675 (3)0.0448 (6)
H31.00450.13531.19320.054*
C40.9194 (4)0.08463 (8)1.0244 (4)0.0465 (6)
H40.92310.06561.12150.056*
C50.8625 (3)0.06948 (7)0.8351 (3)0.0385 (6)
C60.8142 (4)0.02588 (8)0.7898 (4)0.0512 (7)
H60.81810.00680.88670.061*
C70.7624 (4)0.01126 (8)0.6091 (5)0.0632 (8)
H70.7330−0.01760.58200.076*
C80.7539 (5)0.04030 (8)0.4638 (4)0.0667 (8)
H80.71710.03050.33900.080*
C90.7981 (4)0.08248 (8)0.5010 (4)0.0521 (7)
H90.79130.10090.40100.063*
C100.8543 (3)0.09898 (7)0.6881 (3)0.0351 (5)
C110.8922 (3)0.17435 (7)0.5871 (3)0.0358 (5)
H110.83540.16640.46010.043*
C121.0051 (3)0.28023 (7)0.5079 (3)0.0330 (5)
C130.9564 (3)0.30824 (7)0.3373 (3)0.0324 (5)
C140.9349 (3)0.35181 (7)0.3628 (3)0.0363 (5)
H140.95280.36240.48390.044*
C150.8871 (3)0.37955 (7)0.2097 (4)0.0417 (6)
C160.8640 (4)0.36340 (9)0.0300 (4)0.0530 (7)
H160.83250.3819−0.07360.064*
C170.8871 (4)0.32039 (9)0.0040 (4)0.0535 (7)
H170.87260.3100−0.11670.064*
C180.9320 (3)0.29230 (7)0.1567 (3)0.0417 (6)
H180.94570.26310.13870.050*
C190.8793 (5)0.44027 (8)0.3982 (5)0.0690 (9)
H19A0.78770.42660.44860.104*
H19B0.85250.47050.38530.104*
H19C1.01220.43570.48300.104*
H20.836 (3)0.2332 (9)0.363 (2)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0382 (11)0.0332 (10)0.0349 (11)0.0007 (9)0.0070 (9)0.0046 (9)
N20.0449 (12)0.0303 (10)0.0301 (11)−0.0025 (9)0.0024 (9)0.0034 (9)
O10.0689 (12)0.0450 (10)0.0397 (10)−0.0084 (10)0.0143 (10)−0.0079 (8)
O20.0511 (10)0.0396 (9)0.0309 (9)−0.0023 (8)−0.0020 (8)−0.0008 (7)
O30.0633 (13)0.0403 (10)0.0735 (14)0.0055 (9)0.0154 (11)0.0180 (10)
C10.0297 (12)0.0359 (12)0.0311 (13)0.0015 (10)0.0091 (10)0.0030 (10)
C20.0353 (13)0.0369 (13)0.0390 (14)0.0017 (11)0.0114 (11)−0.0016 (11)
C30.0468 (15)0.0558 (16)0.0301 (13)0.0031 (13)0.0108 (12)0.0026 (12)
C40.0460 (15)0.0502 (15)0.0443 (15)0.0037 (13)0.0167 (12)0.0151 (13)
C50.0344 (13)0.0353 (12)0.0469 (15)0.0032 (11)0.0150 (11)0.0058 (11)
C60.0495 (16)0.0413 (14)0.0623 (18)0.0014 (13)0.0184 (14)0.0107 (14)
C70.071 (2)0.0338 (14)0.082 (2)−0.0066 (13)0.0229 (18)−0.0013 (15)
C80.093 (2)0.0472 (16)0.0570 (19)−0.0146 (16)0.0211 (18)−0.0146 (15)
C90.0714 (19)0.0417 (14)0.0436 (15)−0.0093 (13)0.0199 (14)−0.0033 (12)
C100.0328 (12)0.0344 (12)0.0371 (13)0.0016 (10)0.0105 (11)0.0010 (11)
C110.0370 (13)0.0371 (12)0.0296 (12)0.0000 (11)0.0065 (10)−0.0002 (10)
C120.0326 (12)0.0318 (12)0.0305 (12)0.0020 (10)0.0054 (10)−0.0011 (10)
C130.0285 (11)0.0363 (12)0.0282 (12)−0.0034 (10)0.0042 (9)−0.0006 (10)
C140.0327 (12)0.0370 (12)0.0368 (13)−0.0025 (10)0.0084 (10)−0.0009 (11)
C150.0333 (13)0.0387 (13)0.0481 (15)−0.0008 (11)0.0073 (11)0.0112 (12)
C160.0485 (16)0.0640 (18)0.0408 (16)−0.0083 (14)0.0075 (12)0.0168 (14)
C170.0556 (17)0.0742 (19)0.0307 (14)−0.0132 (15)0.0147 (12)−0.0008 (14)
C180.0440 (14)0.0447 (13)0.0358 (14)−0.0041 (12)0.0126 (11)−0.0034 (11)
C190.074 (2)0.0426 (15)0.100 (3)0.0077 (15)0.042 (2)0.0013 (16)

Geometric parameters (Å, °)

N1—C111.284 (3)C7—C81.398 (4)
N1—N21.384 (2)C7—H70.9300
N2—C121.346 (3)C8—C91.359 (3)
N2—H20.905 (10)C8—H80.9300
O1—C21.350 (2)C9—C101.414 (3)
O1—H10.8200C9—H90.9300
O2—C121.235 (3)C11—H110.9300
O3—C151.364 (3)C12—C131.485 (3)
O3—C191.413 (3)C13—C141.387 (3)
C1—C21.384 (3)C13—C181.391 (3)
C1—C101.439 (3)C14—C151.381 (3)
C1—C111.450 (3)C14—H140.9300
C2—C31.408 (3)C15—C161.390 (3)
C3—C41.351 (3)C16—C171.373 (3)
C3—H30.9300C16—H160.9300
C4—C51.414 (3)C17—C181.387 (3)
C4—H40.9300C17—H170.9300
C5—C61.415 (3)C18—H180.9300
C5—C101.418 (3)C19—H19A0.9600
C6—C71.351 (4)C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C11—N1—N2116.33 (18)C9—C10—C5116.9 (2)
C12—N2—N1119.46 (18)C9—C10—C1123.6 (2)
C12—N2—H2121.4 (18)C5—C10—C1119.5 (2)
N1—N2—H2118.1 (18)N1—C11—C1121.1 (2)
C2—O1—H1109.5N1—C11—H11119.5
C15—O3—C19117.2 (2)C1—C11—H11119.5
C2—C1—C10118.92 (19)O2—C12—N2123.04 (19)
C2—C1—C11120.4 (2)O2—C12—C13121.64 (19)
C10—C1—C11120.69 (19)N2—C12—C13115.32 (19)
O1—C2—C1123.1 (2)C14—C13—C18120.0 (2)
O1—C2—C3116.1 (2)C14—C13—C12117.57 (19)
C1—C2—C3120.8 (2)C18—C13—C12122.48 (19)
C4—C3—C2120.6 (2)C15—C14—C13120.5 (2)
C4—C3—H3119.7C15—C14—H14119.7
C2—C3—H3119.7C13—C14—H14119.7
C3—C4—C5121.5 (2)O3—C15—C14125.3 (2)
C3—C4—H4119.3O3—C15—C16115.5 (2)
C5—C4—H4119.3C14—C15—C16119.2 (2)
C4—C5—C6121.6 (2)C17—C16—C15120.6 (2)
C4—C5—C10118.7 (2)C17—C16—H16119.7
C6—C5—C10119.7 (2)C15—C16—H16119.7
C7—C6—C5121.7 (2)C16—C17—C18120.4 (2)
C7—C6—H6119.2C16—C17—H17119.8
C5—C6—H6119.2C18—C17—H17119.8
C6—C7—C8118.8 (2)C17—C18—C13119.3 (2)
C6—C7—H7120.6C17—C18—H18120.4
C8—C7—H7120.6C13—C18—H18120.4
C9—C8—C7121.5 (3)O3—C19—H19A109.5
C9—C8—H8119.3O3—C19—H19B109.5
C7—C8—H8119.3H19A—C19—H19B109.5
C8—C9—C10121.5 (2)O3—C19—H19C109.5
C8—C9—H9119.2H19A—C19—H19C109.5
C10—C9—H9119.2H19B—C19—H19C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.91 (1)1.97 (1)2.842 (3)163 (2)
O1—H1···N10.821.852.574 (2)146

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2461).

References

  • Arunkumar, S., Ramalakshmi, N., Saraswathy, T. & Aruloly, L. (2006). Indian J. Heterocycl. Chem.16, 29–32.
  • Bordoloi, M., Kotoky, R., Mahanta, J. J., Sarma, T. C. & Kanjilal, P. B. (2009). Eur. J. Med. Chem.44, 2754–2757. [PubMed]
  • Bruker (2002). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Galal, S. A., Hegab, K. H., Kassab, A. S., Rodriguez, M. L., Kerwin, S. M., El-Khamry, A. A. & El Diwani, H. I. (2009). Eur. J. Med. Chem.44, 1500–1508. [PubMed]
  • Han, Y.-Y., Li, Y.-H. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1085–o1086. [PMC free article] [PubMed]
  • Qiao, Y., Ju, X., Gao, Z. & Kong, L. (2010). Acta Cryst. E66, o95. [PMC free article] [PubMed]
  • Saxena, H. O., Faridi, U., Srivastava, S., Kumar, J. K., Darokar, M. P., Luqman, S., Chanotiya, C. S., Krishna, V., Negi, A. S. & Khanuja, S. P. S. (2008). Bioorg. Med. Chem. Lett.18, 3914–3918. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Suleiman Gwaram, N., Khaledi, H., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o721. [PMC free article] [PubMed]
  • Sun, Y., Li, H.-G., Wang, X., Fu, S. & Wang, D. (2009). Acta Cryst. E65, o262. [PMC free article] [PubMed]
  • Wang, H.-Y., Fan, C.-G. & Yang, Z.-N. (2010). Acta Cryst. E66, o1.
  • Zia-ur-Rehman, M., Choudary, J. A., Elsegood, M. R. J., Siddiqui, H. L. & Khan, K. M. (2009). Eur. J. Med. Chem.44, 1311–1316. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography