organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721007, People's Republic of China
*Correspondence e-mail: desuoyang@yahoo.com.cn

(Received 21 October 2009; accepted 29 October 2009; online 4 November 2009)

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[Avaji, P. G., Vinod Kumar, C. H., Patil, S. A., Shivananda, K. N. & Nagaraju, C. (2009). Eur. J. Med. Chem. 44, 3552-3559.]); Charkoudian et al. (2007[Charkoudian, L. K., Pham, D. M., Kwon, A. M., Vangeloff, A. D. & Franz, K. J. (2007). J. Chem. Soc. Dalton Trans. pp. 5031-5042.]); Cukurovali et al. (2006[Cukurovali, A., Yilmaz, I., Gur, S. & Kazaz, C. (2006). Eur. J. Med. Chem. 41, 201-207.]). For related structures, see: Yang (2008a[Yang, D.-S. (2008a). Acta Cryst. E64, o1758.],b[Yang, D.-S. (2008b). Acta Cryst. E64, o1759.],c[Yang, D.-S. (2008c). Acta Cryst. E64, o1849.],d[Yang, D.-S. (2008d). Acta Cryst. E64, o1850.],e, 2007a[Yang, D.-S. (2007a). J. Chem. Crystallogr. 37, 343-348.],b[Yang, D.-S. (2007b). Acta Cryst. E63, o3738.],c[Yang, D.-S. (2007c). Acta Cryst. E63, o3739.]); Yang & Guo (2006[Yang, D.-S. & Guo, J.-B. (2006). Acta Cryst. E62, o4414-o4415.]).

[Scheme 1]

Experimental

Crystal data
  • C18H13N3O5

  • Mr = 351.31

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.978

  • 9168 measured reflections

  • 3425 independent reflections

  • 2436 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1 0.82 1.88 2.5987 (18) 146
N1—H1⋯O4i 0.898 (9) 2.144 (10) 3.0361 (19) 172.8 (18)
O5—H5⋯O1ii 0.82 1.88 2.6889 (17) 168
Symmetry codes: (i) -x+2, -y+1, -z; (ii) [-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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 CN 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 C12N2 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 CN 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 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 top
Bruker SMART CCD
diffractometer
3425 independent reflections
Radiation source: fine-focus sealed tube2436 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.975, Tmax = 0.978k = 1010
9168 measured reflectionsl = 2416
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 Å3
1 restraintΔρmin = 0.19 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.19 e Å3
3425 reflectionsΔρmin = 0.19 e Å3
241 parameters
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)
H30.43321.34820.02340.072*
C40.45611 (17)1.1865 (3)0.09781 (10)0.0582 (5)
C50.3359 (2)1.2237 (3)0.15133 (13)0.0833 (8)
H5A0.27561.30130.14280.100*
C60.3090 (3)1.1465 (4)0.21477 (15)0.1025 (11)
H60.22991.17170.24930.123*
C70.3980 (3)1.0294 (3)0.22928 (13)0.1001 (10)
H70.37820.97870.27330.120*
C80.5134 (2)0.9896 (3)0.17908 (11)0.0769 (7)
H80.57210.91160.18890.092*
C90.54456 (19)1.0664 (2)0.11211 (9)0.0541 (5)
C100.66309 (18)1.0299 (2)0.05915 (9)0.0477 (4)
H100.72240.95190.06830.057*
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, º) 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, º) 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, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC18H13N3O5
Mr351.31
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)10.1588 (3), 8.2562 (2), 19.5268 (5)
β (°) 104.867 (1)
V3)1582.95 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.23 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.975, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
9168, 3425, 2436
Rint0.028
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.119, 1.04
No. of reflections3425
No. of parameters241
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.19

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.821.882.5987 (18)146.3
N1—H1···O4i0.898 (9)2.144 (10)3.0361 (19)172.8 (18)
O5—H5···O1ii0.821.882.6889 (17)168.0
Symmetry codes: (i) x+2, y+1, z; (ii) x+5/2, y1/2, z+1/2.
 

Acknowledgements

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

References

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COMMUNICATIONS
ISSN: 2056-9890
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