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Acta Cryst. (2009). E65, o2978    [ doi:10.1107/S1600536809045279 ]

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

D.-S. Yang

Abstract top

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.

Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. Molecular packing as viewed along the b axis. Hydrogen bonds are shown as dashed lines.
3-Hydroxy-N'-(5-hydroxy-2-nitrobenzylidene)-2-naphthohydrazide top
Crystal data top
C18H13N3O5F(000) = 728
Mr = 351.31Dx = 1.474 Mg m−3
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 mm−1
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 top
Bruker SMART CCD
diffractometer		3425 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 top
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 = 1.04 w = 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 Å−3
1 restraintΔρmin = −0.19 e Å−3
0 constraints
Crystal data top
C18H13N3O5V = 1582.95 (7) Å3
Mr = 351.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.1588 (3) ŵ = 0.11 mm−1
b = 8.2562 (2) ÅT = 298 K
c = 19.5268 (5) Å0.23 × 0.20 × 0.20 mm
β = 104.867 (1)°
Data collection top
Bruker SMART CCD
diffractometer		3425 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2436 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.978Rint = 0.028
9168 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119Δρmax = 0.19 e Å−3
S = 1.04Δρmin = −0.19 e Å−3
3425 reflectionsAbsolute structure: ?
241 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

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