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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o101
https://doi.org/10.1107/S1600536807062861

3,5-Dihydr­­oxy-N′-[(2-hydr­­oxy-1-naph­thyl)methyl­ene]benzohydrazide

Yun-Peng Diao,a* Yu-Hong Zhen,a Xu Hana and Sa Denga

aSchool of Pharmacy, Dalian Medical University, Dalian 116044, People's Republic of China
*Correspondence e-mail: diaoyiwen@126.com

(Received 20 November 2007; accepted 24 November 2007; online 6 December 2007)

In the title compound, C18H14N2O4, the dihedral angle between the benzene ring and the naphthyl ring system is 10.1 (2)°. The mol­ecule is nearly planar, with a mean deviation from the plane of 0.141 (2) Å for 24 non-H atoms. An intra­molecular O—H⋯N hydrogen bond forms a pseudo-6-membered ring and the mol­ecules are linked into sheets by inter­molecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For related structures, see: Brückner et al. (2000[Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100-6106.]); Diao (2007[Diao, Y.-P. (2007). Acta Cryst. E63, m1453-m1454.]); Diao et al. (2007[Diao, Y.-P., Shu, X.-H., Zhang, B.-J., Zhen, Y.-H. & Kang, T.-G. (2007). Acta Cryst. E63, m1816.]); Harrop et al. (2003[Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410-411.]); Huang et al. (2007[Huang, S.-S., Zhou, Q. & Diao, Y.-P. (2007). Acta Cryst. E63, o4659.]); Li et al. (2007[Li, K., Huang, S.-S., Zhang, B.-J., Meng, D.-L. & Diao, Y.-P. (2007). Acta Cryst. E63, m2291.]); Ren et al. (2002[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.]).

[Scheme 1]

Experimental

Crystal data

  • C18H14N2O4

  • Mr = 322.31

  • Orthorhombic, P b c a

  • a = 13.354 (3) Å

  • b = 14.133 (3) Å

  • c = 15.077 (3) Å

  • V = 2845.5 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 298 (2) K

  • 0.30 × 0.28 × 0.27 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART (Version 5.625), SAINT (Version 6.01). SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.971

  • 15775 measured reflections

  • 2949 independent reflections

  • 2433 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.110

  • S = 1.03

  • 2949 reflections

  • 223 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O4i 0.82 1.96 2.7671 (15) 167
O2—H2⋯O3i 0.82 1.91 2.7227 (15) 172
O4—H4⋯N2 0.82 1.78 2.5046 (16) 147
N1—H1A⋯O1ii 0.903 (9) 2.141 (12) 2.9929 (16) 157.0 (19)
Symmetry codes: (i) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART (Version 5.625), SAINT (Version 6.01). SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART (Version 5.625), SAINT (Version 6.01). SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000[Bruker (2000). SMART (Version 5.625), SAINT (Version 6.01). SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062861/bi2266sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062861/bi2266Isup2.hkl

checkCIF report


Comment top

Schiff base compounds have received much attention in recent years. Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). As part of our research programme on Schiff base compounds (Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007), we report here the structure of the title compound.

Related literature top

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

Experimental top

2-Hydroxy-1-naphthylaldehyde (1.0 mmol, 172.2 mg) and 3,5-dihydroxybenzoic acid hydrazide (1.0 mmol, 168.2 mg) were dissolved in a methanol solution (70 ml). The mixture was stirred at reflux for 1 h and cooled to room temperature. After keeping the solution in air for two days, yellow block-like crystals were formed.

Refinement top

H1A was located from a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H distances of 0.93 Å, O—H distances of 0.82 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).

Structure description top

Schiff base compounds have received much attention in recent years. Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). As part of our research programme on Schiff base compounds (Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007), we report here the structure of the title compound.

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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Molecular structure with displacement parameters drawn at the 30% probability level for non-H atoms.
3,5-Dihydroxy-N'-[(2-hydroxy-1-naphthyl)methylene]benzohydrazide top
Crystal data top
C18H14N2O4F(000) = 1344
Mr = 322.31Dx = 1.505 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5426 reflections
a = 13.354 (3) Åθ = 2.4–27.8°
b = 14.133 (3) ŵ = 0.11 mm−1
c = 15.077 (3) ÅT = 298 K
V = 2845.5 (10) Å3Block, yellow
Z = 80.30 × 0.28 × 0.27 mm
Data collection top
Bruker SMART CCD
diffractometer		2949 independent reflections
Radiation source: fine-focus sealed tube2433 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −16→15
Tmin = 0.968, Tmax = 0.971k = −17→11
15775 measured reflectionsl = −18→15
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0562P)2 + 0.7945P]
where P = (Fo2 + 2Fc2)/3
2949 reflections(Δ/σ)max = 0.001
223 parametersΔρmax = 0.20 e Å−3
1 restraintΔρmin = −0.19 e Å−3
Crystal data top
C18H14N2O4V = 2845.5 (10) Å3
Mr = 322.31Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.354 (3) ŵ = 0.11 mm−1
b = 14.133 (3) ÅT = 298 K
c = 15.077 (3) Å0.30 × 0.28 × 0.27 mm
Data collection top
Bruker SMART CCD
diffractometer		2949 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2433 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.971Rint = 0.025
15775 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.20 e Å−3
2949 reflectionsΔρmin = −0.19 e Å−3
223 parameters
Special details top

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) top
xyzUiso*/Ueq
O10.70957 (9)−0.44067 (6)0.65672 (7)0.0446 (3)
H10.6882−0.47160.69870.067*
O20.64726 (9)−0.17869 (7)0.84818 (6)0.0425 (3)
H20.6418−0.22140.88470.064*
O30.61626 (10)−0.17124 (7)0.45805 (7)0.0468 (3)
O40.61263 (10)0.02287 (7)0.29946 (7)0.0486 (3)
H40.6170−0.00310.34800.073*
N10.64522 (10)−0.04149 (8)0.53870 (8)0.0359 (3)
N20.62939 (10)0.01212 (8)0.46461 (8)0.0363 (3)
C10.65842 (10)−0.19422 (9)0.60952 (9)0.0308 (3)
C20.67691 (11)−0.28981 (9)0.59712 (9)0.0336 (3)
H2A0.6811−0.31500.54020.040*
C30.68890 (11)−0.34676 (9)0.67002 (9)0.0320 (3)
C40.68089 (11)−0.31096 (9)0.75469 (9)0.0317 (3)
H4A0.6893−0.35040.80350.038*
C50.66031 (10)−0.21629 (9)0.76661 (9)0.0308 (3)
C60.65109 (10)−0.15717 (9)0.69414 (9)0.0317 (3)
H60.6400−0.09280.70220.038*
C70.63939 (11)−0.13645 (9)0.52904 (9)0.0330 (3)
C80.62525 (11)0.10148 (9)0.47179 (9)0.0329 (3)
H80.63240.12990.52710.040*
C90.60931 (10)0.15896 (9)0.39384 (9)0.0306 (3)
C100.60344 (11)0.11717 (10)0.31095 (9)0.0350 (3)
C110.58622 (12)0.17008 (11)0.23410 (10)0.0423 (4)
H110.58230.14010.17930.051*
C120.57537 (12)0.26432 (11)0.23968 (10)0.0428 (4)
H120.56210.29880.18850.051*
C130.58356 (11)0.31214 (10)0.32116 (10)0.0373 (3)
C140.57676 (13)0.41122 (11)0.32600 (12)0.0503 (4)
H140.56440.44570.27460.060*
C150.58771 (15)0.45740 (11)0.40359 (14)0.0577 (5)
H150.58480.52310.40530.069*
C160.60341 (14)0.40619 (11)0.48111 (13)0.0540 (5)
H160.61030.43800.53470.065*
C170.60877 (12)0.30993 (10)0.47952 (11)0.0433 (4)
H170.61820.27700.53230.052*
C180.60030 (10)0.25964 (9)0.39969 (10)0.0325 (3)
H1A0.6770 (14)−0.0170 (14)0.5862 (10)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0747 (8)0.0223 (5)0.0367 (6)0.0096 (5)0.0150 (5)0.0020 (4)
O20.0740 (8)0.0276 (5)0.0261 (5)0.0017 (5)0.0004 (5)−0.0018 (4)
O30.0836 (9)0.0298 (5)0.0271 (5)−0.0008 (5)−0.0043 (5)−0.0024 (4)
O40.0827 (9)0.0315 (6)0.0316 (6)0.0044 (5)−0.0025 (6)−0.0048 (4)
N10.0559 (8)0.0243 (6)0.0275 (6)0.0007 (5)−0.0070 (5)0.0027 (5)
N20.0542 (8)0.0258 (6)0.0290 (6)0.0012 (5)−0.0034 (5)0.0028 (5)
C10.0384 (7)0.0249 (6)0.0291 (7)0.0001 (5)0.0015 (5)0.0017 (5)
C20.0453 (8)0.0275 (7)0.0280 (7)0.0016 (6)0.0047 (6)−0.0022 (5)
C30.0388 (7)0.0219 (6)0.0352 (7)0.0032 (5)0.0054 (6)−0.0003 (5)
C40.0396 (7)0.0267 (6)0.0288 (7)0.0019 (5)0.0017 (6)0.0042 (5)
C50.0380 (7)0.0269 (6)0.0275 (7)−0.0019 (5)0.0007 (5)−0.0027 (5)
C60.0413 (8)0.0224 (6)0.0315 (7)0.0010 (5)0.0006 (6)−0.0010 (5)
C70.0445 (8)0.0257 (6)0.0288 (7)0.0014 (6)0.0020 (6)−0.0011 (5)
C80.0434 (8)0.0262 (6)0.0292 (7)0.0011 (5)−0.0024 (6)−0.0012 (5)
C90.0348 (7)0.0255 (6)0.0315 (7)0.0011 (5)−0.0005 (5)0.0021 (5)
C100.0408 (8)0.0318 (7)0.0324 (7)0.0021 (6)0.0004 (6)0.0007 (6)
C110.0500 (9)0.0474 (9)0.0296 (8)0.0016 (7)−0.0006 (6)0.0010 (6)
C120.0463 (8)0.0475 (9)0.0346 (8)0.0041 (7)0.0014 (7)0.0164 (7)
C130.0350 (7)0.0335 (7)0.0435 (8)0.0025 (6)0.0041 (6)0.0101 (6)
C140.0563 (10)0.0338 (8)0.0607 (11)0.0060 (7)0.0075 (8)0.0189 (7)
C150.0718 (12)0.0246 (7)0.0767 (13)0.0041 (7)0.0076 (10)0.0062 (8)
C160.0724 (12)0.0295 (8)0.0602 (11)0.0032 (7)−0.0002 (9)−0.0059 (7)
C170.0588 (10)0.0289 (7)0.0422 (9)0.0034 (6)−0.0019 (7)−0.0004 (6)
C180.0337 (7)0.0261 (7)0.0378 (8)0.0016 (5)0.0015 (6)0.0040 (6)
Geometric parameters (Å, º) top
O1—C31.3704 (15)C6—H60.930
O1—H10.820C8—C91.4445 (18)
O2—C51.3511 (15)C8—H80.930
O2—H20.820C9—C101.3845 (19)
O3—C71.2177 (17)C9—C181.4307 (18)
O4—C101.3496 (17)C10—C111.398 (2)
O4—H40.820C11—C121.342 (2)
N1—C71.3521 (17)C11—H110.930
N1—N21.3661 (16)C12—C131.406 (2)
N1—H1A0.903 (9)C12—H120.930
N2—C81.2688 (17)C13—C141.405 (2)
C1—C61.3826 (19)C13—C181.4150 (19)
C1—C21.3859 (18)C14—C151.348 (3)
C1—C71.4845 (18)C14—H140.930
C2—C31.3716 (19)C15—C161.391 (3)
C2—H2A0.930C15—H150.930
C3—C41.3774 (19)C16—C171.363 (2)
C4—C51.3776 (17)C16—H160.930
C4—H4A0.930C17—C181.402 (2)
C5—C61.3810 (18)C17—H170.930
C3—O1—H1109.5C10—C9—C18118.36 (12)
C5—O2—H2109.5C10—C9—C8120.20 (12)
C10—O4—H4109.5C18—C9—C8121.44 (12)
C7—N1—N2116.97 (11)O4—C10—C9122.13 (12)
C7—N1—H1A119.6 (14)O4—C10—C11115.90 (13)
N2—N1—H1A120.6 (14)C9—C10—C11121.96 (13)
C8—N2—N1119.28 (12)C12—C11—C10119.77 (14)
C6—C1—C2120.41 (12)C12—C11—H11120.1
C6—C1—C7122.26 (12)C10—C11—H11120.1
C2—C1—C7117.16 (12)C11—C12—C13121.54 (13)
C3—C2—C1118.99 (12)C11—C12—H12119.2
C3—C2—H2A120.5C13—C12—H12119.2
C1—C2—H2A120.5C14—C13—C12121.28 (14)
O1—C3—C2118.34 (12)C14—C13—C18119.30 (15)
O1—C3—C4120.46 (12)C12—C13—C18119.42 (13)
C2—C3—C4121.20 (12)C15—C14—C13121.38 (15)
C3—C4—C5119.55 (12)C15—C14—H14119.3
C3—C4—H4A120.2C13—C14—H14119.3
C5—C4—H4A120.2C14—C15—C16119.60 (15)
O2—C5—C4121.77 (12)C14—C15—H15120.2
O2—C5—C6118.08 (12)C16—C15—H15120.2
C4—C5—C6120.15 (12)C17—C16—C15120.85 (17)
C5—C6—C1119.64 (12)C17—C16—H16119.6
C5—C6—H6120.2C15—C16—H16119.6
C1—C6—H6120.2C16—C17—C18121.13 (15)
O3—C7—N1120.67 (12)C16—C17—H17119.4
O3—C7—C1122.67 (12)C18—C17—H17119.4
N1—C7—C1116.62 (12)C17—C18—C13117.72 (13)
N2—C8—C9119.79 (13)C17—C18—C9123.38 (13)
N2—C8—H8120.1C13—C18—C9118.90 (13)
C9—C8—H8120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.962.7671 (15)167
O2—H2···O3i0.821.912.7227 (15)172
O4—H4···N20.821.782.5046 (16)147
N1—H1A···O1ii0.90 (1)2.14 (1)2.9929 (16)157 (2)
Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC18H14N2O4
Mr322.31
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)13.354 (3), 14.133 (3), 15.077 (3)
V (Å3)2845.5 (10)
Z8
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.30 × 0.28 × 0.27
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.968, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections		15775, 2949, 2433
Rint0.025
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.110, 1.03
No. of reflections2949
No. of parameters223
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.20, −0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.962.7671 (15)166.6
O2—H2···O3i0.821.912.7227 (15)171.8
O4—H4···N20.821.782.5046 (16)146.5
N1—H1A···O1ii0.903 (9)2.141 (12)2.9929 (16)157.0 (19)
Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+3/2, y+1/2, z.
 

Acknowledgements

This project is supported by a research grant from Dalian Medical University.

References

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 First citationBruker (2000). SMART (Version 5.625), SAINT (Version 6.01). SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o101
https://doi.org/10.1107/S1600536807062861
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