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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o996.
Published online 2010 March 31. doi:  10.1107/S160053681001130X
PMCID: PMC2983919

(E)-N′-(2,5-Dimethoxy­benzyl­idene)-2,4-dihydroxy­benzohydrazide

Abstract

In the title compound, C16H16N2O5, the dihedral angle between the two benzene rings is 4.2 (2)° and an intra­molecular O—H(...)O hydrogen bond generates an S(6) ring. In the crystal, mol­ecules are linked into layers lying parallel to the bc plane by O—H(...)O and N—H(...)O hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Bhandari et al. (2008 [triangle]); Sinha et al. (2008 [triangle]). For Schiff base compounds containing 2,5-dimethoxy­benzaldehyde, see: Wang et al. (2009 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

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Object name is e-66-0o996-scheme1.jpg

Experimental

Crystal data

  • C16H16N2O5
  • M r = 316.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o996-efi1.jpg
  • a = 7.8600 (16) Å
  • b = 15.358 (3) Å
  • c = 12.425 (3) Å
  • β = 99.80 (3)°
  • V = 1478.0 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 295 K
  • 0.18 × 0.17 × 0.15 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.981, T max = 0.984
  • 7757 measured reflections
  • 2626 independent reflections
  • 1698 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.112
  • S = 1.02
  • 2626 reflections
  • 212 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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/S160053681001130X/hb5375sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001130X/hb5375Isup2.hkl

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

supplementary crystallographic information

Comment

Schiff base compounds have been of great interest for many years. Some of the complexes derived from Schiff bases have been found to have pharmacological and antitumor properties (Bhandari et al., 2008; Sinha et al., 2008). In this paper, the crystal structure of the title compound, (I), a new Schiff base compound derived from the condensation reaction of 2,4-dihydroxybenzohydrazide with 2,5-dimethoxybenzaldehyde is reported.

The Schiff base molecule of the compound displays a trans configuration with respect to the C=N and C—N bonds(Fig. 1). All the bond lengths are within their normal ranges (Allen et al., 1987) and comparable to other Schiff base compounds containing 2,5-dimethoxybenzaldehyde (Wang et al., 2009). The dihedral angle between the two benzene rings is 4.2 (2)°. Intramolecular O—H···O hydrogen bonds are observed(Table 1). Molecules are linked into layers parallel to the bc plane by O—H···O and N—H···O hydrogen bonds(Fig. 2).

Experimental

2,5-dimethoxybenzaldehyde (0.1 mmol, 16.6 mg) and 2,4-dihydroxybenzohydrazide (0.1 mmol, 16.8 mg) were dissolved in a 95% ethanol solution (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Light yellow blocks of (I) were formed by gradual evaporation of the solvent over a period of three days at room temperature.

Refinement

All H atoms were placed in geometrically idealized positions, with C—H = 0.93–0.96 Å, O—H = 0.82–0.85 Å and N—H = 0.86 Å. Uiso(H) = 1.2Ueq(C,N), and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. The dashed lines indicate hydrogen bonds.
Fig. 2.
The molecular packing of (I). Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in the hydrogen bonds have been omitted for clarity.

Crystal data

C16H16N2O5F(000) = 664
Mr = 316.31Dx = 1.421 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1224 reflections
a = 7.8600 (16) Åθ = 2.7–22.4°
b = 15.358 (3) ŵ = 0.11 mm1
c = 12.425 (3) ÅT = 295 K
β = 99.80 (3)°Block, light yellow
V = 1478.0 (5) Å30.18 × 0.17 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2626 independent reflections
Radiation source: fine-focus sealed tube1698 reflections with I > 2σ(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→8
Tmin = 0.981, Tmax = 0.984k = −17→18
7757 measured reflectionsl = −13→14

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0464P)2 + 0.2321P] where P = (Fo2 + 2Fc2)/3
2626 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.20 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/Ueq
O10.5668 (2)0.18995 (10)0.34476 (11)0.0523 (5)
H10.60070.24040.34380.078*
O20.2931 (2)−0.02763 (10)0.10807 (13)0.0623 (5)
H20.3162−0.05730.16350.093*
O30.6343 (2)0.33256 (9)0.26549 (11)0.0477 (4)
O40.7730 (2)0.58885 (10)−0.13674 (12)0.0569 (5)
O51.0792 (2)0.67891 (10)0.28127 (12)0.0529 (4)
N10.6247 (2)0.35121 (10)0.08522 (13)0.0390 (5)
H1A0.59570.33310.01920.047*
N20.7069 (2)0.42982 (11)0.10809 (13)0.0390 (5)
C10.5091 (3)0.21858 (13)0.15178 (15)0.0329 (5)
C20.5058 (3)0.16342 (13)0.24143 (16)0.0354 (5)
C30.4396 (3)0.08035 (14)0.22852 (16)0.0391 (5)
H30.44360.04390.28870.047*
C40.3674 (3)0.05154 (14)0.12604 (17)0.0421 (6)
C50.3657 (3)0.10522 (15)0.03614 (17)0.0527 (7)
H50.31680.0857−0.03310.063*
C60.4356 (3)0.18663 (14)0.04918 (16)0.0451 (6)
H60.43420.2218−0.01190.054*
C70.5915 (3)0.30376 (13)0.17057 (16)0.0368 (5)
C80.7456 (3)0.47279 (13)0.02779 (17)0.0386 (5)
H80.71600.4520−0.04320.046*
C90.8368 (3)0.55503 (13)0.04948 (16)0.0365 (5)
C100.8507 (3)0.61312 (14)−0.03424 (16)0.0405 (5)
C110.9361 (3)0.69144 (14)−0.01112 (19)0.0463 (6)
H110.94480.7304−0.06720.056*
C121.0081 (3)0.71168 (15)0.09455 (18)0.0468 (6)
H121.06270.76510.10970.056*
C131.0003 (3)0.65342 (14)0.17882 (17)0.0405 (5)
C140.9151 (3)0.57596 (14)0.15574 (17)0.0380 (5)
H140.90940.53660.21190.046*
C151.1064 (3)0.61377 (16)0.36363 (18)0.0576 (7)
H15A0.99700.59380.37850.086*
H15B1.17260.63770.42900.086*
H15C1.16800.56580.33900.086*
C160.8212 (4)0.63418 (17)−0.22690 (18)0.0649 (8)
H16A0.78390.6936−0.22600.097*
H16B0.76790.6070−0.29380.097*
H16C0.94450.6324−0.22160.097*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0799 (12)0.0477 (11)0.0280 (8)−0.0122 (9)0.0054 (8)0.0022 (7)
O20.0909 (13)0.0381 (10)0.0523 (10)−0.0194 (9)−0.0042 (10)0.0057 (8)
O30.0727 (11)0.0384 (9)0.0312 (8)−0.0072 (8)0.0064 (7)−0.0044 (7)
O40.0792 (12)0.0540 (11)0.0359 (9)−0.0129 (9)0.0045 (8)0.0054 (7)
O50.0636 (11)0.0464 (10)0.0445 (9)−0.0064 (8)−0.0026 (8)−0.0036 (8)
N10.0569 (12)0.0289 (10)0.0321 (10)−0.0078 (9)0.0098 (8)−0.0038 (8)
N20.0502 (11)0.0294 (10)0.0384 (10)−0.0049 (8)0.0101 (9)−0.0028 (8)
C10.0414 (12)0.0287 (12)0.0293 (11)0.0003 (9)0.0075 (9)0.0018 (9)
C20.0394 (12)0.0395 (13)0.0283 (11)0.0013 (10)0.0082 (9)0.0015 (10)
C30.0469 (13)0.0365 (13)0.0343 (12)−0.0012 (10)0.0078 (10)0.0097 (10)
C40.0487 (14)0.0327 (13)0.0440 (13)−0.0046 (10)0.0058 (11)0.0039 (10)
C50.0797 (18)0.0412 (14)0.0332 (13)−0.0130 (13)−0.0014 (12)0.0002 (11)
C60.0657 (16)0.0386 (13)0.0300 (12)−0.0073 (11)0.0052 (11)0.0064 (10)
C70.0451 (13)0.0342 (12)0.0315 (12)0.0049 (10)0.0080 (10)0.0016 (10)
C80.0487 (14)0.0341 (13)0.0333 (12)−0.0013 (10)0.0076 (10)−0.0035 (10)
C90.0415 (13)0.0312 (12)0.0378 (12)0.0006 (10)0.0095 (10)0.0001 (10)
C100.0467 (14)0.0383 (13)0.0365 (12)0.0003 (10)0.0071 (11)0.0011 (10)
C110.0558 (15)0.0357 (13)0.0478 (14)−0.0033 (11)0.0099 (12)0.0075 (10)
C120.0521 (15)0.0331 (13)0.0550 (15)−0.0036 (10)0.0090 (12)0.0000 (11)
C130.0420 (13)0.0370 (13)0.0421 (13)−0.0014 (10)0.0061 (10)−0.0039 (10)
C140.0429 (13)0.0329 (12)0.0393 (12)0.0012 (10)0.0098 (10)0.0036 (9)
C150.0654 (17)0.0599 (17)0.0439 (14)−0.0057 (13)−0.0006 (13)0.0041 (12)
C160.089 (2)0.0674 (19)0.0395 (14)0.0021 (16)0.0143 (14)0.0098 (13)

Geometric parameters (Å, °)

O1—C21.355 (2)C5—C61.364 (3)
O1—H10.8200C5—H50.9300
O2—C41.351 (2)C6—H60.9300
O2—H20.8200C8—C91.455 (3)
O3—C71.251 (2)C8—H80.9300
O4—C101.367 (2)C9—C101.389 (3)
O4—C161.424 (3)C9—C141.396 (3)
O5—C131.375 (2)C10—C111.384 (3)
O5—C151.421 (3)C11—C121.374 (3)
N1—C71.348 (2)C11—H110.9300
N1—N21.376 (2)C12—C131.387 (3)
N1—H1A0.8600C12—H120.9300
N2—C81.275 (2)C13—C141.371 (3)
C1—C61.396 (3)C14—H140.9300
C1—C21.403 (3)C15—H15A0.9600
C1—C71.461 (3)C15—H15B0.9600
C2—C31.377 (3)C15—H15C0.9600
C3—C41.376 (3)C16—H16A0.9600
C3—H30.9300C16—H16B0.9600
C4—C51.387 (3)C16—H16C0.9600
C2—O1—H1109.5C9—C8—H8120.7
C4—O2—H2109.5C10—C9—C14118.8 (2)
C10—O4—C16117.56 (18)C10—C9—C8121.21 (19)
C13—O5—C15117.08 (17)C14—C9—C8119.95 (19)
C7—N1—N2117.31 (17)O4—C10—C11123.68 (19)
C7—N1—H1A121.3O4—C10—C9116.29 (19)
N2—N1—H1A121.3C11—C10—C9120.0 (2)
C8—N2—N1117.29 (17)C12—C11—C10120.1 (2)
C6—C1—C2116.88 (19)C12—C11—H11119.9
C6—C1—C7124.33 (18)C10—C11—H11119.9
C2—C1—C7118.77 (18)C11—C12—C13120.8 (2)
O1—C2—C3117.07 (18)C11—C12—H12119.6
O1—C2—C1121.30 (19)C13—C12—H12119.6
C3—C2—C1121.64 (19)C14—C13—O5124.6 (2)
C4—C3—C2119.61 (19)C14—C13—C12119.0 (2)
C4—C3—H3120.2O5—C13—C12116.4 (2)
C2—C3—H3120.2C13—C14—C9121.2 (2)
O2—C4—C3122.76 (19)C13—C14—H14119.4
O2—C4—C5117.22 (19)C9—C14—H14119.4
C3—C4—C5120.0 (2)O5—C15—H15A109.5
C6—C5—C4120.1 (2)O5—C15—H15B109.5
C6—C5—H5120.0H15A—C15—H15B109.5
C4—C5—H5120.0O5—C15—H15C109.5
C5—C6—C1121.75 (19)H15A—C15—H15C109.5
C5—C6—H6119.1H15B—C15—H15C109.5
C1—C6—H6119.1O4—C16—H16A109.5
O3—C7—N1119.56 (19)O4—C16—H16B109.5
O3—C7—C1120.54 (18)H16A—C16—H16B109.5
N1—C7—C1119.89 (18)O4—C16—H16C109.5
N2—C8—C9118.67 (19)H16A—C16—H16C109.5
N2—C8—H8120.7H16B—C16—H16C109.5
C7—N1—N2—C8176.80 (19)N1—N2—C8—C9−178.34 (17)
C6—C1—C2—O1−176.99 (19)N2—C8—C9—C10−166.4 (2)
C7—C1—C2—O14.5 (3)N2—C8—C9—C1414.8 (3)
C6—C1—C2—C32.6 (3)C16—O4—C10—C1117.6 (3)
C7—C1—C2—C3−175.98 (19)C16—O4—C10—C9−163.9 (2)
O1—C2—C3—C4176.54 (19)C14—C9—C10—O4179.36 (18)
C1—C2—C3—C4−3.0 (3)C8—C9—C10—O40.6 (3)
C2—C3—C4—O2−176.9 (2)C14—C9—C10—C11−2.1 (3)
C2—C3—C4—C51.7 (3)C8—C9—C10—C11179.09 (19)
O2—C4—C5—C6178.7 (2)O4—C10—C11—C12178.8 (2)
C3—C4—C5—C60.0 (4)C9—C10—C11—C120.4 (3)
C4—C5—C6—C1−0.4 (4)C10—C11—C12—C131.7 (3)
C2—C1—C6—C5−0.8 (3)C15—O5—C13—C1414.2 (3)
C7—C1—C6—C5177.6 (2)C15—O5—C13—C12−166.4 (2)
N2—N1—C7—O30.6 (3)C11—C12—C13—C14−1.9 (3)
N2—N1—C7—C1−178.22 (17)C11—C12—C13—O5178.70 (19)
C6—C1—C7—O3170.6 (2)O5—C13—C14—C9179.43 (19)
C2—C1—C7—O3−11.0 (3)C12—C13—C14—C90.0 (3)
C6—C1—C7—N1−10.6 (3)C10—C9—C14—C131.9 (3)
C2—C1—C7—N1167.86 (19)C8—C9—C14—C13−179.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O30.821.762.495 (2)148
O2—H2···O3i0.821.922.664 (2)151
N1—H1A···O1ii0.862.173.012 (2)166

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5375).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem.16, 1822–1831. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Sinha, D., Tiwari, A. K., Singh, S., Shukla, G., Mishra, P., Chandra, H. & Mishra, A. K. (2008). Eur. J. Med. Chem.43, 160–165. [PubMed]
  • Wang, S.-Y., Yuan, L., Xu, L., Zhang, Z., Diao, Y.-P. & Lv, D.-C. (2009). Acta Cryst. E65, o1154. [PMC free article] [PubMed]

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