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organic compounds
3,5-Dihydroxy-N′-[(2-hydroxy-1-naphthyl)methylene]benzohydrazide
aSchool of Pharmacy, Dalian Medical University, Dalian 116044, People's Republic of China
*Correspondence e-mail: diaoyiwen@126.com
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); Diao (2007
); Diao et al. (2007
); Harrop et al. (2003
); Huang et al. (2007
); Li et al. (2007
); Ren et al. (2002
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000
); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000
); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536807062861/bi2266sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062861/bi2266Isup2.hkl
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.
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).
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).
Data collection: SMART (Bruker, 2000); cell
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). ![]() | Fig. 1. Molecular structure with displacement parameters drawn at the 30% probability level for non-H atoms. |
C18H14N2O4 | F(000) = 1344 |
Mr = 322.31 | Dx = 1.505 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5426 reflections |
a = 13.354 (3) Å | θ = 2.4–27.8° |
b = 14.133 (3) Å | µ = 0.11 mm−1 |
c = 15.077 (3) Å | T = 298 K |
V = 2845.5 (10) Å3 | Block, yellow |
Z = 8 | 0.30 × 0.28 × 0.27 mm |
Bruker SMART CCD diffractometer | 2949 independent reflections |
Radiation source: fine-focus sealed tube | 2433 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 26.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −16→15 |
Tmin = 0.968, Tmax = 0.971 | k = −17→11 |
15775 measured reflections | l = −18→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H 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 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
C18H14N2O4 | V = 2845.5 (10) Å3 |
Mr = 322.31 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 13.354 (3) Å | µ = 0.11 mm−1 |
b = 14.133 (3) Å | T = 298 K |
c = 15.077 (3) Å | 0.30 × 0.28 × 0.27 mm |
Bruker SMART CCD diffractometer | 2949 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2433 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.971 | Rint = 0.025 |
15775 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 1 restraint |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.20 e Å−3 |
2949 reflections | Δρmin = −0.19 e Å−3 |
223 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.70957 (9) | −0.44067 (6) | 0.65672 (7) | 0.0446 (3) | |
H1 | 0.6882 | −0.4716 | 0.6987 | 0.067* | |
O2 | 0.64726 (9) | −0.17869 (7) | 0.84818 (6) | 0.0425 (3) | |
H2 | 0.6418 | −0.2214 | 0.8847 | 0.064* | |
O3 | 0.61626 (10) | −0.17124 (7) | 0.45805 (7) | 0.0468 (3) | |
O4 | 0.61263 (10) | 0.02287 (7) | 0.29946 (7) | 0.0486 (3) | |
H4 | 0.6170 | −0.0031 | 0.3480 | 0.073* | |
N1 | 0.64522 (10) | −0.04149 (8) | 0.53870 (8) | 0.0359 (3) | |
N2 | 0.62939 (10) | 0.01212 (8) | 0.46461 (8) | 0.0363 (3) | |
C1 | 0.65842 (10) | −0.19422 (9) | 0.60952 (9) | 0.0308 (3) | |
C2 | 0.67691 (11) | −0.28981 (9) | 0.59712 (9) | 0.0336 (3) | |
H2A | 0.6811 | −0.3150 | 0.5402 | 0.040* | |
C3 | 0.68890 (11) | −0.34676 (9) | 0.67002 (9) | 0.0320 (3) | |
C4 | 0.68089 (11) | −0.31096 (9) | 0.75469 (9) | 0.0317 (3) | |
H4A | 0.6893 | −0.3504 | 0.8035 | 0.038* | |
C5 | 0.66031 (10) | −0.21629 (9) | 0.76661 (9) | 0.0308 (3) | |
C6 | 0.65109 (10) | −0.15717 (9) | 0.69414 (9) | 0.0317 (3) | |
H6 | 0.6400 | −0.0928 | 0.7022 | 0.038* | |
C7 | 0.63939 (11) | −0.13645 (9) | 0.52904 (9) | 0.0330 (3) | |
C8 | 0.62525 (11) | 0.10148 (9) | 0.47179 (9) | 0.0329 (3) | |
H8 | 0.6324 | 0.1299 | 0.5271 | 0.040* | |
C9 | 0.60931 (10) | 0.15896 (9) | 0.39384 (9) | 0.0306 (3) | |
C10 | 0.60344 (11) | 0.11717 (10) | 0.31095 (9) | 0.0350 (3) | |
C11 | 0.58622 (12) | 0.17008 (11) | 0.23410 (10) | 0.0423 (4) | |
H11 | 0.5823 | 0.1401 | 0.1793 | 0.051* | |
C12 | 0.57537 (12) | 0.26432 (11) | 0.23968 (10) | 0.0428 (4) | |
H12 | 0.5621 | 0.2988 | 0.1885 | 0.051* | |
C13 | 0.58356 (11) | 0.31214 (10) | 0.32116 (10) | 0.0373 (3) | |
C14 | 0.57676 (13) | 0.41122 (11) | 0.32600 (12) | 0.0503 (4) | |
H14 | 0.5644 | 0.4457 | 0.2746 | 0.060* | |
C15 | 0.58771 (15) | 0.45740 (11) | 0.40359 (14) | 0.0577 (5) | |
H15 | 0.5848 | 0.5231 | 0.4053 | 0.069* | |
C16 | 0.60341 (14) | 0.40619 (11) | 0.48111 (13) | 0.0540 (5) | |
H16 | 0.6103 | 0.4380 | 0.5347 | 0.065* | |
C17 | 0.60877 (12) | 0.30993 (10) | 0.47952 (11) | 0.0433 (4) | |
H17 | 0.6182 | 0.2770 | 0.5323 | 0.052* | |
C18 | 0.60030 (10) | 0.25964 (9) | 0.39969 (10) | 0.0325 (3) | |
H1A | 0.6770 (14) | −0.0170 (14) | 0.5862 (10) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0747 (8) | 0.0223 (5) | 0.0367 (6) | 0.0096 (5) | 0.0150 (5) | 0.0020 (4) |
O2 | 0.0740 (8) | 0.0276 (5) | 0.0261 (5) | 0.0017 (5) | 0.0004 (5) | −0.0018 (4) |
O3 | 0.0836 (9) | 0.0298 (5) | 0.0271 (5) | −0.0008 (5) | −0.0043 (5) | −0.0024 (4) |
O4 | 0.0827 (9) | 0.0315 (6) | 0.0316 (6) | 0.0044 (5) | −0.0025 (6) | −0.0048 (4) |
N1 | 0.0559 (8) | 0.0243 (6) | 0.0275 (6) | 0.0007 (5) | −0.0070 (5) | 0.0027 (5) |
N2 | 0.0542 (8) | 0.0258 (6) | 0.0290 (6) | 0.0012 (5) | −0.0034 (5) | 0.0028 (5) |
C1 | 0.0384 (7) | 0.0249 (6) | 0.0291 (7) | 0.0001 (5) | 0.0015 (5) | 0.0017 (5) |
C2 | 0.0453 (8) | 0.0275 (7) | 0.0280 (7) | 0.0016 (6) | 0.0047 (6) | −0.0022 (5) |
C3 | 0.0388 (7) | 0.0219 (6) | 0.0352 (7) | 0.0032 (5) | 0.0054 (6) | −0.0003 (5) |
C4 | 0.0396 (7) | 0.0267 (6) | 0.0288 (7) | 0.0019 (5) | 0.0017 (6) | 0.0042 (5) |
C5 | 0.0380 (7) | 0.0269 (6) | 0.0275 (7) | −0.0019 (5) | 0.0007 (5) | −0.0027 (5) |
C6 | 0.0413 (8) | 0.0224 (6) | 0.0315 (7) | 0.0010 (5) | 0.0006 (6) | −0.0010 (5) |
C7 | 0.0445 (8) | 0.0257 (6) | 0.0288 (7) | 0.0014 (6) | 0.0020 (6) | −0.0011 (5) |
C8 | 0.0434 (8) | 0.0262 (6) | 0.0292 (7) | 0.0011 (5) | −0.0024 (6) | −0.0012 (5) |
C9 | 0.0348 (7) | 0.0255 (6) | 0.0315 (7) | 0.0011 (5) | −0.0005 (5) | 0.0021 (5) |
C10 | 0.0408 (8) | 0.0318 (7) | 0.0324 (7) | 0.0021 (6) | 0.0004 (6) | 0.0007 (6) |
C11 | 0.0500 (9) | 0.0474 (9) | 0.0296 (8) | 0.0016 (7) | −0.0006 (6) | 0.0010 (6) |
C12 | 0.0463 (8) | 0.0475 (9) | 0.0346 (8) | 0.0041 (7) | 0.0014 (7) | 0.0164 (7) |
C13 | 0.0350 (7) | 0.0335 (7) | 0.0435 (8) | 0.0025 (6) | 0.0041 (6) | 0.0101 (6) |
C14 | 0.0563 (10) | 0.0338 (8) | 0.0607 (11) | 0.0060 (7) | 0.0075 (8) | 0.0189 (7) |
C15 | 0.0718 (12) | 0.0246 (7) | 0.0767 (13) | 0.0041 (7) | 0.0076 (10) | 0.0062 (8) |
C16 | 0.0724 (12) | 0.0295 (8) | 0.0602 (11) | 0.0032 (7) | −0.0002 (9) | −0.0059 (7) |
C17 | 0.0588 (10) | 0.0289 (7) | 0.0422 (9) | 0.0034 (6) | −0.0019 (7) | −0.0004 (6) |
C18 | 0.0337 (7) | 0.0261 (7) | 0.0378 (8) | 0.0016 (5) | 0.0015 (6) | 0.0040 (6) |
O1—C3 | 1.3704 (15) | C6—H6 | 0.930 |
O1—H1 | 0.820 | C8—C9 | 1.4445 (18) |
O2—C5 | 1.3511 (15) | C8—H8 | 0.930 |
O2—H2 | 0.820 | C9—C10 | 1.3845 (19) |
O3—C7 | 1.2177 (17) | C9—C18 | 1.4307 (18) |
O4—C10 | 1.3496 (17) | C10—C11 | 1.398 (2) |
O4—H4 | 0.820 | C11—C12 | 1.342 (2) |
N1—C7 | 1.3521 (17) | C11—H11 | 0.930 |
N1—N2 | 1.3661 (16) | C12—C13 | 1.406 (2) |
N1—H1A | 0.903 (9) | C12—H12 | 0.930 |
N2—C8 | 1.2688 (17) | C13—C14 | 1.405 (2) |
C1—C6 | 1.3826 (19) | C13—C18 | 1.4150 (19) |
C1—C2 | 1.3859 (18) | C14—C15 | 1.348 (3) |
C1—C7 | 1.4845 (18) | C14—H14 | 0.930 |
C2—C3 | 1.3716 (19) | C15—C16 | 1.391 (3) |
C2—H2A | 0.930 | C15—H15 | 0.930 |
C3—C4 | 1.3774 (19) | C16—C17 | 1.363 (2) |
C4—C5 | 1.3776 (17) | C16—H16 | 0.930 |
C4—H4A | 0.930 | C17—C18 | 1.402 (2) |
C5—C6 | 1.3810 (18) | C17—H17 | 0.930 |
C3—O1—H1 | 109.5 | C10—C9—C18 | 118.36 (12) |
C5—O2—H2 | 109.5 | C10—C9—C8 | 120.20 (12) |
C10—O4—H4 | 109.5 | C18—C9—C8 | 121.44 (12) |
C7—N1—N2 | 116.97 (11) | O4—C10—C9 | 122.13 (12) |
C7—N1—H1A | 119.6 (14) | O4—C10—C11 | 115.90 (13) |
N2—N1—H1A | 120.6 (14) | C9—C10—C11 | 121.96 (13) |
C8—N2—N1 | 119.28 (12) | C12—C11—C10 | 119.77 (14) |
C6—C1—C2 | 120.41 (12) | C12—C11—H11 | 120.1 |
C6—C1—C7 | 122.26 (12) | C10—C11—H11 | 120.1 |
C2—C1—C7 | 117.16 (12) | C11—C12—C13 | 121.54 (13) |
C3—C2—C1 | 118.99 (12) | C11—C12—H12 | 119.2 |
C3—C2—H2A | 120.5 | C13—C12—H12 | 119.2 |
C1—C2—H2A | 120.5 | C14—C13—C12 | 121.28 (14) |
O1—C3—C2 | 118.34 (12) | C14—C13—C18 | 119.30 (15) |
O1—C3—C4 | 120.46 (12) | C12—C13—C18 | 119.42 (13) |
C2—C3—C4 | 121.20 (12) | C15—C14—C13 | 121.38 (15) |
C3—C4—C5 | 119.55 (12) | C15—C14—H14 | 119.3 |
C3—C4—H4A | 120.2 | C13—C14—H14 | 119.3 |
C5—C4—H4A | 120.2 | C14—C15—C16 | 119.60 (15) |
O2—C5—C4 | 121.77 (12) | C14—C15—H15 | 120.2 |
O2—C5—C6 | 118.08 (12) | C16—C15—H15 | 120.2 |
C4—C5—C6 | 120.15 (12) | C17—C16—C15 | 120.85 (17) |
C5—C6—C1 | 119.64 (12) | C17—C16—H16 | 119.6 |
C5—C6—H6 | 120.2 | C15—C16—H16 | 119.6 |
C1—C6—H6 | 120.2 | C16—C17—C18 | 121.13 (15) |
O3—C7—N1 | 120.67 (12) | C16—C17—H17 | 119.4 |
O3—C7—C1 | 122.67 (12) | C18—C17—H17 | 119.4 |
N1—C7—C1 | 116.62 (12) | C17—C18—C13 | 117.72 (13) |
N2—C8—C9 | 119.79 (13) | C17—C18—C9 | 123.38 (13) |
N2—C8—H8 | 120.1 | C13—C18—C9 | 118.90 (13) |
C9—C8—H8 | 120.1 |
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 | 0.90 (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 formula | C18H14N2O4 |
Mr | 322.31 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 298 |
a, b, c (Å) | 13.354 (3), 14.133 (3), 15.077 (3) |
V (Å3) | 2845.5 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.30 × 0.28 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.968, 0.971 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15775, 2949, 2433 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.110, 1.03 |
No. of reflections | 2949 |
No. of parameters | 223 |
No. of restraints | 1 |
H-atom treatment | H 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).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4i | 0.82 | 1.96 | 2.7671 (15) | 166.6 |
O2—H2···O3i | 0.82 | 1.91 | 2.7227 (15) | 171.8 |
O4—H4···N2 | 0.82 | 1.78 | 2.5046 (16) | 146.5 |
N1—H1A···O1ii | 0.903 (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
Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100–6106. Web of Science CSD CrossRef PubMed CAS Google Scholar
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. Google Scholar
Diao, Y.-P. (2007). Acta Cryst. E63, m1453–m1454. Web of Science CSD CrossRef IUCr Journals Google Scholar
Diao, Y.-P., Shu, X.-H., Zhang, B.-J., Zhen, Y.-H. & Kang, T.-G. (2007). Acta Cryst. E63, m1816. CSD CrossRef IUCr Journals Google Scholar
Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410–411. Web of Science CSD CrossRef Google Scholar
Huang, S.-S., Zhou, Q. & Diao, Y.-P. (2007). Acta Cryst. E63, o4659. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, K., Huang, S.-S., Zhang, B.-J., Meng, D.-L. & Diao, Y.-P. (2007). Acta Cryst. E63, m2291. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
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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.