PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2070.
Published online 2008 October 4. doi:  10.1107/S1600536808031395
PMCID: PMC2959633

(E)-4-Bromo-N′-(2-hydr­oxy-1-naphthyl­methyl­ene)benzohydrazide

Abstract

The title compound, C18H13BrN2O2, was synthesized by the reaction of 2-hydr­oxy-1-naphthaldehyde with 4-bromo­benzohydrazide. This Schiff base mol­ecule has an E configuration about the C=N bond and is almost planar, the dihedral angle between the mean planes through the substituted benzene ring and the naphthyl system being 6.6 (2)°. There is an intra­molecular O—H(...)N hydrogen bond involving the naphthyl hydr­oxy substituent and the N′ atom of the hydrazide group. In the crystal structure, mol­ecules are linked through inter­molecular N—-H(...)O hydrogen bonds to form chains extending along the b direction.

Related literature

For related structures, see: Brückner et al. (2000 [triangle]); Diao (2007 [triangle]); Diao et al. (2007 [triangle], 2008 [triangle]); Harrop et al. (2003 [triangle]); Huang et al. (2007 [triangle]); Li et al. (2007 [triangle]); Ren et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2070-scheme1.jpg

Experimental

Crystal data

  • C18H13BrN2O2
  • M r = 369.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2070-efi1.jpg
  • a = 6.185 (2) Å
  • b = 4.7638 (19) Å
  • c = 25.689 (10) Å
  • β = 95.449 (7)°
  • V = 753.5 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.74 mm−1
  • T = 298 (2) K
  • 0.30 × 0.30 × 0.28 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.494, T max = 0.514 (expected range = 0.446–0.464)
  • 5817 measured reflections
  • 3119 independent reflections
  • 2443 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.101
  • S = 0.90
  • 3119 reflections
  • 212 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.24 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1493 Friedel pairs
  • Flack parameter: 0.026 (12)

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; 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/S1600536808031395/su2066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031395/su2066Isup2.hkl

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

supplementary crystallographic information

Comment

Schiff base compounds have been found to have potential pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). Recently, a few Schiff base compounds obtained from the reaction of aldehydes with benzohydrazides have been reported (Diao et al., 2008; Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007). As a further study of such compounds, we report here on the structure of the title compound.

The title compound, a Schiff base synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 4-bromobenzohydrazide, is almost planar (Fig. 1), with the dihedral angle between the mean planes of the substituted benzene ring and the naphthyl ring being only 6.6 (2)°. The torsion angles C4—C6—N1—N2 and C8—C7—N2—N1 are 0.9 (3) and 2.9 (3)°, respectively. There is an intramolecular O-H···N hydrogen bond involving the naphthyl hydroxyl substituent and the NH H-atom of the hydrazide group (Table 1).

In the crystal molecules are linked via N–H···O intermolecular hydrogen bonds (Table 1), to form chains extending in the b direction (Fig. 2).

Experimental

4-Bromobenzaldehyde (0.1 mmol, 18.5 mg) and 2-hydroxy-1-naphthaldehyde (0.1 mmol, 17.2 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 1 h and cooled to room temperature. After keeping the solution in air for alomost two weeks, yellow block-like crystals of the title compound were formed.

Refinement

Atom H1 was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. The other H atoms were placed in calculated positions and treated as riding atoms, with C–H = 0.93 Å, O–H = 0.82 Å, and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound with displacement parameters drawn at the 30% probability level.
Fig. 2.
A persepctive view along the a axis of the crystal packing of the title compound.

Crystal data

C18H13BrN2O2F(000) = 372
Mr = 369.21Dx = 1.627 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
a = 6.185 (2) ÅCell parameters from 1589 reflections
b = 4.7638 (19) Åθ = 2.6–24.5°
c = 25.689 (10) ŵ = 2.74 mm1
β = 95.449 (7)°T = 298 K
V = 753.5 (5) Å3Block, yellow
Z = 20.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer3119 independent reflections
Radiation source: fine-focus sealed tube2443 reflections with I > 2σ(I)
graphiteRint = 0.034
ω scansθmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −7→7
Tmin = 0.494, Tmax = 0.514k = −6→6
5817 measured reflectionsl = −32→32

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101w = 1/[σ2(Fo2) + ]
S = 0.90(Δ/σ)max = 0.001
3119 reflectionsΔρmax = 0.31 e Å3
212 parametersΔρmin = −0.24 e Å3
3 restraintsAbsolute structure: Flack (1983), 1493 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.026 (12)

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
Br11.08310 (11)0.22527 (11)1.13545 (4)0.0685 (2)
O10.2012 (5)−0.3701 (5)0.99811 (12)0.0474 (7)
O2−0.3678 (6)−0.2844 (6)0.91908 (13)0.0509 (8)
H2−0.2458−0.24810.93270.076*
N10.1759 (5)0.0647 (6)0.96274 (13)0.0379 (7)
N2−0.0057 (5)−0.0129 (6)0.93167 (12)0.0377 (7)
C180.7851 (7)0.2520 (7)1.04481 (17)0.0407 (9)
H180.87750.39021.03420.049*
C10.8295 (7)0.1191 (9)1.09188 (16)0.0433 (9)
C20.6996 (7)−0.0854 (9)1.10869 (16)0.0480 (10)
H2A0.7329−0.17111.14100.058*
C30.5173 (7)−0.1632 (8)1.07685 (17)0.0432 (10)
H30.4282−0.30521.08750.052*
C40.4659 (6)−0.0328 (7)1.02954 (15)0.0340 (8)
C50.6012 (6)0.1770 (7)1.01362 (16)0.0369 (8)
H50.56730.26690.98180.044*
C60.2705 (6)−0.1305 (8)0.99609 (15)0.0350 (8)
C7−0.0776 (6)0.1545 (8)0.89501 (16)0.0357 (8)
H7−0.00230.31900.88930.043*
C8−0.2727 (6)0.0903 (7)0.86278 (15)0.0361 (8)
C9−0.4138 (6)−0.1175 (8)0.87700 (16)0.0399 (9)
C10−0.6139 (7)−0.1627 (9)0.8477 (2)0.0513 (11)
H10−0.7084−0.29750.85870.062*
C11−0.6716 (6)−0.0146 (9)0.80394 (19)0.0527 (11)
H11−0.8065−0.04620.78570.063*
C12−0.5319 (7)0.1866 (8)0.78536 (19)0.0459 (10)
C13−0.5851 (8)0.3322 (10)0.7382 (2)0.0558 (12)
H13−0.71770.29630.71910.067*
C14−0.4491 (8)0.5229 (10)0.71980 (18)0.0596 (12)
H14−0.48610.61560.68830.071*
C15−0.2513 (8)0.5774 (10)0.74925 (17)0.0568 (11)
H15−0.15760.71010.73720.068*
C16−0.1927 (6)0.4422 (8)0.79472 (15)0.0441 (9)
H16−0.05870.48060.81290.053*
C17−0.3314 (6)0.2444 (7)0.81494 (17)0.0377 (9)
H10.209 (11)0.245 (4)0.969 (3)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0451 (2)0.0994 (4)0.0583 (3)−0.0070 (3)−0.00903 (17)−0.0151 (3)
O10.0489 (17)0.0246 (13)0.068 (2)−0.0093 (12)−0.0010 (14)0.0020 (13)
O20.055 (2)0.0432 (16)0.055 (2)−0.0164 (13)0.0070 (15)−0.0067 (14)
N10.0431 (18)0.0268 (15)0.0425 (18)−0.0060 (14)−0.0022 (14)−0.0048 (13)
N20.0343 (15)0.0308 (15)0.0473 (19)−0.0038 (13)0.0002 (13)−0.0074 (14)
C180.036 (2)0.043 (2)0.044 (2)−0.0092 (17)0.0070 (17)−0.0058 (17)
C10.036 (2)0.047 (2)0.046 (3)−0.0004 (18)0.0002 (17)−0.0128 (19)
C20.050 (2)0.050 (3)0.042 (2)0.000 (2)−0.0038 (19)0.0053 (19)
C30.044 (2)0.035 (2)0.051 (3)−0.0049 (17)0.0040 (19)0.0034 (17)
C40.038 (2)0.0274 (18)0.037 (2)−0.0041 (15)0.0040 (15)−0.0030 (15)
C50.038 (2)0.0343 (19)0.038 (2)−0.0062 (15)0.0045 (16)−0.0027 (15)
C60.038 (2)0.0250 (18)0.043 (2)−0.0006 (16)0.0105 (17)−0.0058 (16)
C70.035 (2)0.0306 (18)0.041 (2)−0.0062 (15)0.0040 (16)−0.0041 (16)
C80.036 (2)0.0308 (18)0.041 (2)−0.0011 (16)0.0023 (16)−0.0111 (16)
C90.041 (2)0.035 (2)0.044 (2)−0.0055 (17)0.0084 (17)−0.0101 (17)
C100.038 (2)0.049 (2)0.068 (3)−0.0138 (19)0.008 (2)−0.015 (2)
C110.031 (2)0.060 (3)0.064 (3)−0.0061 (18)−0.0082 (18)−0.023 (2)
C120.038 (2)0.044 (2)0.055 (3)0.0017 (17)−0.0037 (19)−0.0178 (18)
C130.049 (3)0.057 (3)0.057 (3)0.009 (2)−0.013 (2)−0.015 (2)
C140.067 (3)0.068 (3)0.043 (3)0.010 (3)−0.003 (2)−0.001 (2)
C150.059 (3)0.066 (3)0.046 (3)−0.002 (2)0.008 (2)−0.001 (2)
C160.038 (2)0.051 (3)0.044 (2)−0.0058 (18)0.0023 (17)−0.0005 (19)
C170.033 (2)0.036 (2)0.043 (2)0.0018 (15)0.0005 (16)−0.0104 (16)

Geometric parameters (Å, °)

Br1—C11.907 (4)C7—C81.430 (5)
O1—C61.222 (5)C7—H70.9300
O2—C91.350 (5)C8—C91.391 (5)
O2—H20.8200C8—C171.448 (6)
N1—C61.359 (5)C9—C101.403 (6)
N1—N21.366 (4)C10—C111.346 (7)
N1—H10.89 (3)C10—H100.9300
N2—C71.281 (5)C11—C121.404 (6)
C18—C11.369 (6)C11—H110.9300
C18—C51.375 (6)C12—C131.407 (7)
C18—H180.9300C12—C171.419 (6)
C1—C21.359 (6)C13—C141.354 (7)
C2—C31.379 (6)C13—H130.9300
C2—H2A0.9300C14—C151.400 (7)
C3—C41.375 (5)C14—H140.9300
C3—H30.9300C15—C161.353 (6)
C4—C51.389 (5)C15—H150.9300
C4—C61.490 (5)C16—C171.406 (6)
C5—H50.9300C16—H160.9300
C9—O2—H2109.5C9—C8—C17118.1 (3)
C6—N1—N2117.7 (3)C7—C8—C17120.8 (3)
C6—N1—H1118 (5)O2—C9—C8122.7 (4)
N2—N1—H1121 (5)O2—C9—C10116.6 (4)
C7—N2—N1118.0 (3)C8—C9—C10120.8 (4)
C1—C18—C5118.7 (4)C11—C10—C9121.2 (4)
C1—C18—H18120.7C11—C10—H10119.4
C5—C18—H18120.7C9—C10—H10119.4
C2—C1—C18122.5 (4)C10—C11—C12121.3 (4)
C2—C1—Br1118.8 (3)C10—C11—H11119.4
C18—C1—Br1118.7 (3)C12—C11—H11119.4
C1—C2—C3118.6 (4)C11—C12—C13121.9 (4)
C1—C2—H2A120.7C11—C12—C17119.0 (4)
C3—C2—H2A120.7C13—C12—C17119.1 (4)
C4—C3—C2120.7 (4)C14—C13—C12121.9 (4)
C4—C3—H3119.7C14—C13—H13119.0
C2—C3—H3119.7C12—C13—H13119.0
C3—C4—C5119.3 (4)C13—C14—C15118.4 (4)
C3—C4—C6118.4 (3)C13—C14—H14120.8
C5—C4—C6122.2 (4)C15—C14—H14120.8
C18—C5—C4120.2 (4)C16—C15—C14121.8 (5)
C18—C5—H5119.9C16—C15—H15119.1
C4—C5—H5119.9C14—C15—H15119.1
O1—C6—N1122.3 (3)C15—C16—C17121.0 (4)
O1—C6—C4122.4 (3)C15—C16—H16119.5
N1—C6—C4115.3 (3)C17—C16—H16119.5
N2—C7—C8120.5 (3)C16—C17—C12117.7 (4)
N2—C7—H7119.8C16—C17—C8122.7 (4)
C8—C7—H7119.8C12—C17—C8119.5 (4)
C9—C8—C7121.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.89 (3)1.99 (3)2.841 (4)160 (6)
O2—H2···N20.821.862.580 (4)145

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2066).

References

  • Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem.39, 6100–6106. [PubMed]
  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Diao, Y.-P. (2007). Acta Cryst. E63, m1453–m1454.
  • Diao, Y.-P., Shu, X.-H., Zhang, B.-J., Zhen, Y.-H. & Kang, T.-G. (2007). Acta Cryst. E63, m1816.
  • Diao, Y.-P., Zhen, Y.-H., Han, X. & Deng, S. (2008). Acta Cryst. E64, o101. [PMC free article] [PubMed]
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410–411. [PubMed]
  • Huang, S.-S., Zhou, Q. & Diao, Y.-P. (2007). Acta Cryst. E63, o4659.
  • Li, K., Huang, S.-S., Zhang, B.-J., Meng, D.-L. & Diao, Y.-P. (2007). Acta Cryst. E63, m2291.
  • Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem.45, 410–419. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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