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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1600.
Published online 2009 June 17. doi:  10.1107/S1600536809022533
PMCID: PMC2969212

(E)-3-Bromo-N′-(2-hydr­oxy-1-naphthyl­idene)benzohydrazide

Abstract

The title compound, C18H13BrN2O2, was synthesized by the reaction of 2-hydr­oxy-1-naphthaldehyde with an equimolar quantity of 3-bromo­benzohydrazide in methanol. The dihedral angle between the benzene ring and the naphthyl ring system is 18.3 (2)°. An intra­molecular O—H(...)N hydrogen bond is observed between the phenolate O and imine N atoms. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O and C—H(...)O hydrogen bonds, forming a chain running along [101].

Related literature

For crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 [triangle]); Fun et al. (2008 [triangle]); Li & Ban (2009 [triangle]); Zhu et al. (2009 [triangle]); Yang (2007 [triangle]); You et al. (2008 [triangle]). For hydrazone compounds reported previously by our group, see: Qu et al. (2008 [triangle]); Yang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1600-scheme1.jpg

Experimental

Crystal data

  • C18H13BrN2O2
  • M r = 369.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1600-efi1.jpg
  • a = 7.257 (1) Å
  • b = 31.229 (2) Å
  • c = 7.327 (1) Å
  • β = 109.186 (2)°
  • V = 1568.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.63 mm−1
  • T = 298 K
  • 0.27 × 0.24 × 0.23 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.505, T max = 0.548
  • 9563 measured reflections
  • 3393 independent reflections
  • 2177 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.130
  • S = 1.03
  • 3393 reflections
  • 212 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.95 e Å−3
  • Δρmin = −0.74 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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/S1600536809022533/rz2335sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022533/rz2335Isup2.hkl

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

Acknowledgments

The Vital Foundation of Ankang University (project No. 2008AKXY012) and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02JK202) are gratefully acknowledged.

supplementary crystallographic information

Comment

Study on the crystal structures of hydrazone derivatives is a hot topic in structural chemistry. In the last few years, the crystal structures of a large number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008), the title new hydrazone compound derived from the reaction of 2-hydroxynaphthaldehyde with an equimolar quantity of 3-bromobenzohydrazide is reported.

In the title compound compound (Fig. 1), the dihedral angle between the benzene ring system and the naphthyl ring is 18.3 (2)°. An intramolecular O—H···N hydrogen bond is observed between the phenolate O and imine N atoms. In the crystal structure, molecules are linked through intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) to form a chain running along [101] (Fig. 2).

Experimental

The title compound was prepared by refluxing equimolar quantities of 2-hydroxynaphthaldehyde with 3-bromobenzohydrazide in methanol. Colourless block-like crystals were formed by slow evaporation of the solution in air.

Refinement

H2 was located in 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 idealized positions and constrained to ride on their parent atoms, with C–H distances of 0.93 Å, O–H distance 0.82 Å, and with Uiso(H) set at 1.2Ueq(C) or 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. The intermolecular O—H···N hydrogen bond is shown as a dashed line.
Fig. 2.
The molecular packing of the title compound, viewed along the c axis. Hydrogen bonds are drawn as dashed lines.

Crystal data

C18H13BrN2O2F(000) = 744
Mr = 369.21Dx = 1.564 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2089 reflections
a = 7.257 (1) Åθ = 2.5–24.1°
b = 31.229 (2) ŵ = 2.63 mm1
c = 7.327 (1) ÅT = 298 K
β = 109.186 (2)°Block, colourless
V = 1568.3 (3) Å30.27 × 0.24 × 0.23 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3393 independent reflections
Radiation source: fine-focus sealed tube2177 reflections with I > 2σ(I)
graphiteRint = 0.042
ω scansθmax = 27.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −9→9
Tmin = 0.505, Tmax = 0.548k = −33→39
9563 measured reflectionsl = −9→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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0521P)2 + 1.3512P] where P = (Fo2 + 2Fc2)/3
3393 reflections(Δ/σ)max = 0.001
212 parametersΔρmax = 0.95 e Å3
1 restraintΔρmin = −0.74 e Å3

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 > 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)

xyzUiso*/Ueq
Br10.65464 (7)0.056963 (13)0.64773 (9)0.0777 (2)
N10.5623 (4)0.28551 (9)0.3163 (4)0.0421 (7)
N20.5913 (4)0.25667 (9)0.4663 (4)0.0422 (7)
O10.4950 (4)0.30515 (9)−0.0423 (4)0.0582 (7)
H10.50180.28940.04910.087*
O20.4065 (4)0.20685 (8)0.2666 (3)0.0519 (7)
C10.6106 (5)0.35584 (11)0.2181 (5)0.0370 (8)
C20.5493 (5)0.34517 (12)0.0233 (5)0.0431 (8)
C30.5414 (6)0.37649 (14)−0.1167 (5)0.0548 (10)
H30.50410.3687−0.24630.066*
C40.5868 (6)0.41757 (14)−0.0669 (6)0.0564 (11)
H40.57890.4377−0.16280.068*
C50.6461 (5)0.43074 (12)0.1279 (5)0.0460 (9)
C60.6938 (6)0.47395 (13)0.1836 (7)0.0596 (11)
H60.68650.49430.08890.072*
C70.7495 (7)0.48622 (14)0.3699 (8)0.0687 (13)
H70.77650.51490.40260.082*
C80.7662 (7)0.45580 (14)0.5133 (7)0.0664 (12)
H80.80700.46430.64220.080*
C90.7234 (6)0.41362 (12)0.4677 (6)0.0536 (10)
H90.73610.39390.56620.064*
C100.6602 (5)0.39952 (11)0.2733 (5)0.0389 (8)
C110.6256 (5)0.32334 (11)0.3624 (5)0.0391 (8)
H110.68290.33020.49230.047*
C120.5114 (5)0.21769 (11)0.4285 (5)0.0377 (8)
C130.5620 (5)0.18763 (11)0.5957 (5)0.0380 (8)
C140.5772 (5)0.14454 (11)0.5566 (5)0.0414 (8)
H140.55390.13550.43000.050*
C150.6263 (5)0.11530 (12)0.7037 (6)0.0468 (9)
C160.6536 (6)0.12784 (14)0.8898 (6)0.0589 (11)
H160.68400.10770.98860.071*
C170.6359 (6)0.17036 (15)0.9303 (6)0.0599 (11)
H170.65460.17891.05670.072*
C180.5903 (5)0.20061 (12)0.7827 (5)0.0466 (9)
H180.57900.22940.81010.056*
H20.682 (5)0.2631 (14)0.580 (4)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0680 (3)0.0401 (3)0.1356 (5)0.0096 (2)0.0481 (3)0.0197 (3)
N10.0472 (18)0.0343 (15)0.0368 (16)0.0008 (13)0.0029 (13)0.0047 (13)
N20.0506 (19)0.0339 (15)0.0331 (15)−0.0033 (13)0.0015 (13)0.0031 (13)
O10.075 (2)0.0555 (17)0.0404 (15)−0.0080 (15)0.0144 (14)−0.0071 (13)
O20.0624 (18)0.0407 (14)0.0370 (14)−0.0040 (12)−0.0048 (12)−0.0023 (11)
C10.0329 (18)0.0374 (18)0.0396 (19)0.0012 (14)0.0102 (14)0.0042 (15)
C20.039 (2)0.048 (2)0.042 (2)0.0022 (16)0.0129 (16)0.0051 (17)
C30.060 (3)0.069 (3)0.035 (2)0.002 (2)0.0138 (18)0.0068 (19)
C40.057 (3)0.061 (3)0.055 (3)0.011 (2)0.023 (2)0.025 (2)
C50.039 (2)0.045 (2)0.056 (2)0.0066 (16)0.0200 (17)0.0120 (18)
C60.054 (3)0.043 (2)0.090 (3)0.0031 (19)0.034 (2)0.020 (2)
C70.075 (3)0.038 (2)0.100 (4)−0.008 (2)0.039 (3)−0.004 (2)
C80.074 (3)0.054 (3)0.073 (3)−0.013 (2)0.027 (2)−0.012 (2)
C90.066 (3)0.042 (2)0.054 (2)−0.0050 (19)0.022 (2)−0.0023 (18)
C100.0304 (18)0.0401 (18)0.047 (2)0.0021 (14)0.0135 (15)0.0042 (16)
C110.039 (2)0.0365 (19)0.0364 (18)0.0031 (15)0.0057 (15)0.0020 (15)
C120.0345 (19)0.0372 (18)0.0370 (19)0.0027 (14)0.0059 (15)−0.0028 (15)
C130.0315 (18)0.0393 (19)0.0391 (19)−0.0002 (15)0.0061 (14)0.0039 (15)
C140.0347 (19)0.0401 (19)0.048 (2)−0.0020 (15)0.0123 (16)0.0012 (17)
C150.035 (2)0.043 (2)0.064 (3)0.0002 (16)0.0188 (18)0.0123 (18)
C160.049 (3)0.067 (3)0.060 (3)0.001 (2)0.016 (2)0.026 (2)
C170.057 (3)0.082 (3)0.038 (2)−0.004 (2)0.0129 (18)0.009 (2)
C180.048 (2)0.048 (2)0.042 (2)−0.0047 (17)0.0140 (17)−0.0012 (17)

Geometric parameters (Å, °)

Br1—C151.894 (4)C6—H60.9300
N1—C111.272 (4)C7—C81.392 (6)
N1—N21.383 (4)C7—H70.9300
N2—C121.338 (4)C8—C91.369 (6)
N2—H20.90 (3)C8—H80.9300
O1—C21.350 (4)C9—C101.415 (5)
O1—H10.8200C9—H90.9300
O2—C121.227 (4)C11—H110.9300
C1—C21.389 (5)C12—C131.490 (5)
C1—C101.435 (5)C13—C181.378 (5)
C1—C111.444 (5)C13—C141.388 (5)
C2—C31.405 (5)C14—C151.368 (5)
C3—C41.345 (6)C14—H140.9300
C3—H30.9300C15—C161.369 (6)
C4—C51.410 (6)C16—C171.375 (6)
C4—H40.9300C16—H160.9300
C5—C61.419 (6)C17—C181.391 (5)
C5—C101.423 (5)C17—H170.9300
C6—C71.346 (6)C18—H180.9300
C11—N1—N2116.5 (3)C8—C9—H9119.4
C12—N2—N1119.1 (3)C10—C9—H9119.4
C12—N2—H2122 (3)C9—C10—C5117.4 (3)
N1—N2—H2118 (3)C9—C10—C1123.2 (3)
C2—O1—H1109.5C5—C10—C1119.4 (3)
C2—C1—C10118.9 (3)N1—C11—C1121.7 (3)
C2—C1—C11120.4 (3)N1—C11—H11119.2
C10—C1—C11120.7 (3)C1—C11—H11119.2
O1—C2—C1123.0 (3)O2—C12—N2122.7 (3)
O1—C2—C3116.6 (3)O2—C12—C13121.8 (3)
C1—C2—C3120.4 (3)N2—C12—C13115.5 (3)
C4—C3—C2121.2 (4)C18—C13—C14119.6 (3)
C4—C3—H3119.4C18—C13—C12123.2 (3)
C2—C3—H3119.4C14—C13—C12117.1 (3)
C3—C4—C5121.3 (4)C15—C14—C13120.2 (4)
C3—C4—H4119.4C15—C14—H14119.9
C5—C4—H4119.4C13—C14—H14119.9
C4—C5—C6122.2 (4)C14—C15—C16120.6 (4)
C4—C5—C10118.7 (4)C14—C15—Br1119.4 (3)
C6—C5—C10119.1 (4)C16—C15—Br1120.0 (3)
C7—C6—C5121.7 (4)C15—C16—C17119.8 (4)
C7—C6—H6119.1C15—C16—H16120.1
C5—C6—H6119.1C17—C16—H16120.1
C6—C7—C8119.6 (4)C16—C17—C18120.2 (4)
C6—C7—H7120.2C16—C17—H17119.9
C8—C7—H7120.2C18—C17—H17119.9
C9—C8—C7121.0 (4)C13—C18—C17119.5 (4)
C9—C8—H8119.5C13—C18—H18120.2
C7—C8—H8119.5C17—C18—H18120.2
C8—C9—C10121.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.584 (4)146
N2—H2···O2i0.90 (3)1.99 (2)2.840 (4)159 (4)
C11—H11···O2i0.922.423.138 (4)134

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: RZ2335).

References

  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707. [PMC free article] [PubMed]
  • Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o189. [PMC free article] [PubMed]
  • Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o1466. [PMC free article] [PubMed]
  • Qu, L.-Z., Yang, T., Cao, G.-B. & Wang, X.-Y. (2008). Acta Cryst. E64, o2061. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yang, D.-S. (2007). J. Chem. Crystallogr.37, 343-348.
  • Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186. [PMC free article] [PubMed]
  • You, Z.-L., Dai, W.-M., Xu, X.-Q. & Hu, Y.-Q. (2008). Pol. J. Chem.82, 2215-2219.
  • Zhu, C.-G., Wei, Y.-J. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o85. [PMC free article] [PubMed]

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