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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o2978.
Published online 2009 November 4. doi:  10.1107/S1600536809045279
PMCID: PMC2971756

3-Hydr­oxy-N′-(5-hydr­oxy-2-nitro­benzyl­idene)-2-naphthohydrazide

Abstract

The mol­ecule of the title compound, C18H13N3O5, displays an E configuration with respect to the C=N double bond. The dihedral angle between the benzene ring and the naphthyl system is 1.1 (2)°. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O and O—H(...)O hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological and structural chemistry of hydrazone compounds, see: Avaji et al. (2009 [triangle]); Charkoudian et al. (2007 [triangle]); Cukurovali et al. (2006 [triangle]). For related structures, see: Yang (2008a [triangle],b [triangle],c [triangle],d [triangle],e, 2007a [triangle],b [triangle],c [triangle]); Yang & Guo (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2978-scheme1.jpg

Experimental

Crystal data

  • C18H13N3O5
  • M r = 351.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2978-efi1.jpg
  • a = 10.1588 (3) Å
  • b = 8.2562 (2) Å
  • c = 19.5268 (5) Å
  • β = 104.867 (1)°
  • V = 1582.95 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 K
  • 0.23 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.975, T max = 0.978
  • 9168 measured reflections
  • 3425 independent reflections
  • 2436 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.119
  • S = 1.04
  • 3425 reflections
  • 241 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.19 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/S1600536809045279/bh2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045279/bh2256Isup2.hkl

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

Acknowledgments

The author acknowledges Baoji University of Arts and Sciences for support.

supplementary crystallographic information

Comment

Hydrazone compounds have been of great interest for their versatile biological and structural chemistry (Avaji et al., 2009; Charkoudian et al., 2007; Cukurovali et al., 2006). Recently, we have reported a few hydrazone compounds (Yang, 2008a,b,c,d,e, 2007a,b,c; Yang & Guo, 2006). As a further investigation of this work, the crystal structure of the title new hydrazone compound is reported.

In the title compound (Fig. 1), the molecule displays an E configuration with respect to the C═N double bond. The C13···C18 benzene ring forms dihedral angles of 28.6 (2) and 1.1 (2)°, respectively, with the O3—N3—O4 nitro group and the C1···C10 naphthyl ring. All bond lengths are within normal ranges. The C12═N2 bond length of 1.266 (2) Å, conforms to the value for a formal double bond. The bond length of 1.341 (2) Å between atoms C11 and N1 is intermediate between a C—N single bond and a C═N double bond, because of conjugation effects in the molecule.

In the crystal structure, molecules are linked through intermolecular N—H···O and O—H···O hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2).

Experimental

5-Hydroxy-2-nitrobenzaldehyde (0.1 mmol, 16.7 mg) and 3-hydroxy-2-naphthohydrazide (0.1 mmol, 20.2 mg) were dissolved in CHCl3 (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of 3 days, at room temperature.

Refinement

Atom H1 was located in a difference map and refined isotropically, with N—H distance restrained to 0.90 (1) Å. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with O—H distances of 0.82 Å, C—H distances of 0.93 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as a dashed line.
Fig. 2.
Molecular packing as viewed along the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C18H13N3O5F(000) = 728
Mr = 351.31Dx = 1.474 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2463 reflections
a = 10.1588 (3) Åθ = 2.5–26.6°
b = 8.2562 (2) ŵ = 0.11 mm1
c = 19.5268 (5) ÅT = 298 K
β = 104.867 (1)°Block, colorless
V = 1582.95 (7) Å30.23 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer3425 independent reflections
Radiation source: fine-focus sealed tube2436 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.975, Tmax = 0.978k = −10→10
9168 measured reflectionsl = −24→16

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0503P)2 + 0.3232P] where P = (Fo2 + 2Fc2)/3
3425 reflections(Δ/σ)max < 0.001
241 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = −0.19 e Å3
0 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.88109 (14)0.92607 (17)0.05530 (7)0.0462 (4)
N21.00455 (13)0.88709 (16)0.10140 (7)0.0446 (3)
N31.20940 (14)0.48961 (18)0.04801 (7)0.0461 (3)
O10.86564 (13)1.16125 (15)0.11112 (6)0.0575 (4)
O20.63397 (15)1.31345 (18)0.08033 (7)0.0689 (4)
H20.70841.28540.10520.103*
O31.13711 (14)0.56430 (16)−0.00173 (6)0.0612 (4)
O41.24674 (14)0.34954 (16)0.04217 (7)0.0695 (4)
O51.38574 (15)0.75885 (19)0.31532 (6)0.0721 (4)
H51.45650.71600.33770.108*
C10.69456 (16)1.10569 (19)0.00579 (8)0.0407 (4)
C20.60609 (17)1.2299 (2)0.01840 (9)0.0485 (4)
C30.49048 (18)1.2674 (3)−0.03235 (10)0.0601 (5)
H30.43321.3482−0.02340.072*
C40.45611 (17)1.1865 (3)−0.09781 (10)0.0582 (5)
C50.3359 (2)1.2237 (3)−0.15133 (13)0.0833 (8)
H5A0.27561.3013−0.14280.100*
C60.3090 (3)1.1465 (4)−0.21477 (15)0.1025 (11)
H60.22991.1717−0.24930.123*
C70.3980 (3)1.0294 (3)−0.22928 (13)0.1001 (10)
H70.37820.9787−0.27330.120*
C80.5134 (2)0.9896 (3)−0.17908 (11)0.0769 (7)
H80.57210.9116−0.18890.092*
C90.54456 (19)1.0664 (2)−0.11211 (9)0.0541 (5)
C100.66309 (18)1.0299 (2)−0.05915 (9)0.0477 (4)
H100.72240.9519−0.06830.057*
C110.81986 (16)1.06728 (19)0.06131 (8)0.0417 (4)
C121.04643 (17)0.7455 (2)0.09371 (9)0.0468 (4)
H120.99350.67740.05960.056*
C131.17752 (16)0.68736 (18)0.13789 (8)0.0398 (4)
C141.25482 (16)0.56598 (18)0.11681 (8)0.0381 (3)
C151.37767 (16)0.51385 (19)0.16009 (9)0.0429 (4)
H151.42760.43420.14430.051*
C161.42572 (16)0.5796 (2)0.22626 (8)0.0440 (4)
H161.50940.54710.25500.053*
C171.34847 (18)0.6951 (2)0.24990 (8)0.0466 (4)
C181.22688 (17)0.7487 (2)0.20549 (8)0.0481 (4)
H181.17720.82800.22160.058*
H10.8395 (18)0.8513 (19)0.0237 (8)0.066 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0433 (8)0.0423 (8)0.0426 (8)0.0066 (6)−0.0077 (6)−0.0034 (6)
N20.0416 (7)0.0449 (8)0.0399 (7)0.0064 (6)−0.0033 (6)0.0013 (6)
N30.0441 (8)0.0456 (8)0.0486 (8)−0.0067 (6)0.0117 (7)−0.0072 (7)
O10.0632 (8)0.0469 (7)0.0482 (7)0.0076 (6)−0.0119 (6)−0.0087 (6)
O20.0754 (10)0.0743 (10)0.0563 (8)0.0261 (8)0.0159 (7)−0.0026 (7)
O30.0687 (9)0.0642 (9)0.0433 (7)−0.0101 (7)0.0007 (6)−0.0002 (6)
O40.0683 (9)0.0559 (8)0.0786 (9)0.0076 (7)0.0085 (7)−0.0274 (7)
O50.0725 (10)0.0899 (11)0.0412 (7)0.0308 (8)−0.0088 (6)−0.0124 (7)
C10.0390 (8)0.0370 (8)0.0416 (8)−0.0019 (7)0.0022 (7)0.0075 (7)
C20.0475 (10)0.0517 (10)0.0469 (10)0.0047 (8)0.0133 (8)0.0101 (8)
C30.0431 (10)0.0710 (13)0.0687 (13)0.0150 (9)0.0189 (9)0.0243 (11)
C40.0378 (9)0.0711 (13)0.0591 (12)−0.0109 (9)0.0004 (8)0.0282 (10)
C50.0427 (11)0.1106 (19)0.0836 (16)−0.0086 (12)−0.0074 (11)0.0461 (15)
C60.0652 (15)0.120 (2)0.0910 (19)−0.0332 (16)−0.0366 (14)0.0452 (18)
C70.113 (2)0.0834 (18)0.0686 (15)−0.0412 (17)−0.0400 (15)0.0161 (13)
C80.0945 (16)0.0613 (13)0.0542 (12)−0.0199 (12)−0.0187 (11)0.0049 (10)
C90.0536 (11)0.0486 (10)0.0485 (10)−0.0154 (9)−0.0080 (8)0.0144 (8)
C100.0518 (10)0.0375 (8)0.0459 (9)−0.0020 (8)−0.0022 (8)0.0045 (7)
C110.0437 (9)0.0382 (8)0.0384 (8)0.0000 (7)0.0016 (7)0.0026 (7)
C120.0455 (9)0.0440 (9)0.0434 (9)0.0023 (8)−0.0022 (7)−0.0052 (7)
C130.0403 (8)0.0366 (8)0.0387 (8)0.0020 (7)0.0031 (7)0.0030 (7)
C140.0422 (8)0.0333 (8)0.0376 (8)−0.0044 (7)0.0082 (7)0.0001 (6)
C150.0438 (9)0.0363 (8)0.0497 (9)0.0043 (7)0.0141 (8)0.0035 (7)
C160.0409 (9)0.0443 (9)0.0430 (9)0.0060 (7)0.0038 (7)0.0090 (7)
C170.0506 (10)0.0494 (10)0.0350 (8)0.0053 (8)0.0022 (7)0.0009 (7)
C180.0499 (10)0.0462 (9)0.0436 (9)0.0140 (8)0.0037 (8)−0.0029 (7)

Geometric parameters (Å, °)

N1—C111.341 (2)C5—H5A0.9300
N1—N21.3812 (18)C6—C71.402 (4)
N1—H10.898 (9)C6—H60.9300
N2—C121.266 (2)C7—C81.362 (3)
N3—O31.2235 (18)C7—H70.9300
N3—O41.2315 (18)C8—C91.414 (3)
N3—C141.448 (2)C8—H80.9300
O1—C111.2378 (18)C9—C101.404 (2)
O2—C21.357 (2)C10—H100.9300
O2—H20.8200C12—C131.469 (2)
O5—C171.343 (2)C12—H120.9300
O5—H50.8200C13—C181.382 (2)
C1—C101.376 (2)C13—C141.399 (2)
C1—C21.426 (2)C14—C151.384 (2)
C1—C111.479 (2)C15—C161.371 (2)
C2—C31.364 (2)C15—H150.9300
C3—C41.405 (3)C16—C171.387 (2)
C3—H30.9300C16—H160.9300
C4—C91.414 (3)C17—C181.387 (2)
C4—C51.422 (3)C18—H180.9300
C5—C61.357 (4)
C11—N1—N2120.64 (13)C9—C8—H8119.8
C11—N1—H1120.7 (13)C10—C9—C4118.26 (17)
N2—N1—H1118.4 (13)C10—C9—C8122.1 (2)
C12—N2—N1114.48 (14)C4—C9—C8119.63 (18)
O3—N3—O4122.43 (14)C1—C10—C9122.28 (17)
O3—N3—C14120.03 (14)C1—C10—H10118.9
O4—N3—C14117.54 (14)C9—C10—H10118.9
C2—O2—H2109.5O1—C11—N1121.64 (14)
C17—O5—H5109.5O1—C11—C1121.38 (15)
C10—C1—C2118.58 (15)N1—C11—C1116.98 (14)
C10—C1—C11122.05 (15)N2—C12—C13120.90 (15)
C2—C1—C11119.31 (14)N2—C12—H12119.5
O2—C2—C3118.43 (17)C13—C12—H12119.5
O2—C2—C1121.50 (15)C18—C13—C14116.75 (14)
C3—C2—C1120.07 (17)C18—C13—C12119.55 (15)
C2—C3—C4121.34 (18)C14—C13—C12123.64 (14)
C2—C3—H3119.3C15—C14—C13121.96 (14)
C4—C3—H3119.3C15—C14—N3116.99 (14)
C3—C4—C9119.42 (16)C13—C14—N3121.04 (14)
C3—C4—C5122.1 (2)C16—C15—C14119.98 (15)
C9—C4—C5118.4 (2)C16—C15—H15120.0
C6—C5—C4120.2 (3)C14—C15—H15120.0
C6—C5—H5A119.9C15—C16—C17119.39 (15)
C4—C5—H5A119.9C15—C16—H16120.3
C5—C6—C7121.3 (2)C17—C16—H16120.3
C5—C6—H6119.4O5—C17—C16122.72 (15)
C7—C6—H6119.4O5—C17—C18117.25 (16)
C8—C7—C6120.1 (3)C16—C17—C18120.03 (15)
C8—C7—H7119.9C13—C18—C17121.79 (16)
C6—C7—H7119.9C13—C18—H18119.1
C7—C8—C9120.3 (3)C17—C18—H18119.1
C7—C8—H8119.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O10.821.882.5987 (18)146
N1—H1···O4i0.90 (1)2.14 (1)3.0361 (19)173 (2)
O5—H5···O1ii0.821.882.6889 (17)168

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+5/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2256).

References

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  • Cukurovali, A., Yilmaz, I., Gur, S. & Kazaz, C. (2006). Eur. J. Med. Chem. 41, 201–207. [PubMed]
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