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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2615.
Published online 2009 October 3. doi:  10.1107/S1600536809039300
PMCID: PMC2970986

(E)-N′-(2,5-Dimethoxy­benzyl­idene)-3,4-dihydroxy­benzohydrazide monohydrate

Abstract

In the title compound, C16H16N2O5·H2O, the dihedral angle between the two benzene rings is 25.9 (1)°. Intra­molecular O—H(...)O and N—H(...)O hydrogen bonds are observed. In the crystal, the components are linked into a three-dimensional network by O—H(...)O and O—H(...)(O,O) hydrogen bonds.

Related literature

For related structures, see: Pu (2008 [triangle]); Wang et al. (2009 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o2615-scheme1.jpg

Experimental

Crystal data

  • C16H16N2O5·H2O
  • M r = 334.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2615-efi1.jpg
  • a = 10.2573 (8) Å
  • b = 12.4199 (10) Å
  • c = 14.0042 (8) Å
  • β = 119.666 (4)°
  • V = 1550.2 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 295 K
  • 0.20 × 0.18 × 0.17 mm

Data collection

  • Siemens SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Siemens, 1996 [triangle]) T min = 0.978, T max = 0.981
  • 7993 measured reflections
  • 2735 independent reflections
  • 2110 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.098
  • S = 1.02
  • 2735 reflections
  • 220 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.15 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/S1600536809039300/hb5111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039300/hb5111Isup2.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. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Pu, 2008). As a part of our on going investigation in this field we have determined the crystal structure of the title compound, (I).

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 normal ranges (Allen et al., 1987), and are comparable to other Schiff base compounds containing 2,5-dimethoxybenzaldehyde (Wang et al., 2009). The dihedral angle between the two benzene rings is 25.9 (1)°. Intramolecular O—H···O and N—H···O hydrogen bonds are observed (Table 1). Molecules are linked into three-dimensional network by O—H···O hydrogen bonds (Fig. 2).

Experimental

2,5-Dimethoxybenzaldehyde (0.1 mmol, 16.6 mg) and 3,4-dihydroxybenzohydrazide (0.1 mmol, 16.9 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 six days at room temperature.

Refinement

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

C16H16N2O5·H2OF(000) = 704
Mr = 334.32Dx = 1.432 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2817 reflections
a = 10.2573 (8) Åθ = 2.3–28.0°
b = 12.4199 (10) ŵ = 0.11 mm1
c = 14.0042 (8) ÅT = 295 K
β = 119.666 (4)°Block, light yellow
V = 1550.2 (2) Å30.20 × 0.18 × 0.17 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer2735 independent reflections
Radiation source: fine-focus sealed tube2110 reflections with I > 2σ(I)
graphiteRint = 0.060
ω scansθmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Siemens, 1996)h = −12→10
Tmin = 0.978, Tmax = 0.981k = −14→14
7993 measured reflectionsl = −16→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.098w = 1/[σ2(Fo2) + (0.0472P)2 + 0.0836P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2735 reflectionsΔρmax = 0.30 e Å3
220 parametersΔρmin = −0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0092 (15)

Special details

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)

xyzUiso*/Ueq
O10.29807 (12)0.63600 (8)0.00386 (8)0.0415 (3)
H10.34780.67630.05580.062*
O20.25882 (12)0.49266 (9)−0.15328 (8)0.0451 (3)
H20.24790.5582−0.15610.068*
O30.50018 (13)0.24912 (8)0.30247 (8)0.0462 (3)
O40.83630 (14)0.60874 (9)0.70864 (9)0.0516 (3)
O50.84768 (13)0.17847 (9)0.81326 (9)0.0554 (4)
O60.71520 (13)0.60032 (9)0.33312 (9)0.0469 (3)
H170.73550.57470.28570.070*
H180.65600.65300.30210.070*
N10.56517 (14)0.42030 (10)0.36286 (9)0.0374 (3)
H1A0.56580.48730.34770.045*
N20.62828 (14)0.38569 (10)0.47007 (10)0.0386 (3)
C10.43573 (16)0.38751 (11)0.16836 (11)0.0311 (4)
C20.39529 (16)0.49534 (12)0.14219 (11)0.0324 (4)
H2A0.40680.54310.19700.039*
C30.33846 (15)0.53178 (12)0.03578 (12)0.0306 (3)
C40.31715 (16)0.45885 (12)−0.04685 (11)0.0328 (4)
C50.35509 (17)0.35223 (13)−0.02211 (12)0.0380 (4)
H50.34080.3041−0.07730.046*
C60.41477 (17)0.31659 (12)0.08543 (12)0.0363 (4)
H60.44090.24450.10200.044*
C70.50232 (16)0.34597 (12)0.28220 (12)0.0336 (4)
C80.69125 (17)0.45828 (13)0.54315 (12)0.0378 (4)
H80.68790.53000.52300.045*
C90.76899 (16)0.42735 (13)0.65942 (11)0.0346 (4)
C100.84706 (17)0.50414 (13)0.74194 (12)0.0364 (4)
C110.92900 (17)0.46990 (14)0.84979 (12)0.0410 (4)
H110.98250.52000.90490.049*
C120.93298 (18)0.36251 (14)0.87737 (12)0.0429 (4)
H120.98990.34100.95030.051*
C130.85242 (18)0.28700 (13)0.79661 (12)0.0396 (4)
C140.77166 (17)0.32066 (13)0.68859 (12)0.0390 (4)
H140.71760.27020.63400.047*
C150.9048 (2)0.68888 (14)0.79085 (14)0.0512 (5)
H15A0.86010.68840.83700.077*
H15B0.89030.75820.75670.077*
H15C1.01020.67430.83440.077*
C160.9447 (2)0.13853 (17)0.92118 (15)0.0683 (6)
H16A1.04610.15940.94420.102*
H16B0.93820.06140.92100.102*
H16C0.91510.16780.97100.102*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0508 (7)0.0360 (6)0.0266 (6)0.0042 (5)0.0106 (5)0.0021 (5)
O20.0597 (8)0.0478 (7)0.0227 (6)0.0049 (5)0.0166 (6)0.0044 (5)
O30.0635 (8)0.0327 (6)0.0257 (6)−0.0063 (5)0.0093 (6)0.0017 (5)
O40.0685 (8)0.0415 (7)0.0295 (6)−0.0086 (6)0.0126 (6)−0.0060 (5)
O50.0657 (8)0.0467 (7)0.0324 (7)−0.0016 (6)0.0079 (6)0.0076 (5)
O60.0586 (8)0.0424 (7)0.0345 (6)0.0024 (5)0.0190 (6)0.0026 (5)
N10.0499 (8)0.0325 (7)0.0176 (6)−0.0026 (6)0.0075 (6)0.0025 (5)
N20.0463 (8)0.0408 (8)0.0196 (6)−0.0029 (6)0.0093 (6)0.0009 (6)
C10.0319 (8)0.0328 (8)0.0222 (7)−0.0040 (6)0.0084 (6)−0.0006 (6)
C20.0339 (8)0.0351 (8)0.0226 (8)−0.0032 (6)0.0097 (7)−0.0039 (6)
C30.0280 (8)0.0335 (8)0.0243 (8)0.0000 (6)0.0084 (6)0.0013 (6)
C40.0326 (8)0.0427 (9)0.0200 (8)−0.0026 (7)0.0107 (7)0.0008 (6)
C50.0471 (10)0.0385 (9)0.0254 (8)−0.0036 (7)0.0156 (7)−0.0065 (7)
C60.0429 (9)0.0322 (8)0.0277 (8)−0.0012 (7)0.0128 (7)−0.0007 (7)
C70.0361 (9)0.0337 (9)0.0238 (8)−0.0029 (6)0.0094 (7)−0.0008 (6)
C80.0433 (9)0.0373 (9)0.0265 (8)−0.0001 (7)0.0125 (7)−0.0012 (7)
C90.0335 (9)0.0432 (9)0.0216 (8)0.0009 (6)0.0095 (7)−0.0026 (6)
C100.0388 (9)0.0410 (9)0.0268 (8)−0.0007 (7)0.0143 (7)−0.0034 (7)
C110.0438 (10)0.0484 (10)0.0233 (8)−0.0048 (7)0.0109 (7)−0.0091 (7)
C120.0454 (10)0.0542 (11)0.0204 (8)0.0024 (8)0.0097 (7)0.0005 (7)
C130.0425 (10)0.0427 (10)0.0278 (8)0.0002 (7)0.0130 (7)0.0009 (7)
C140.0413 (9)0.0433 (10)0.0240 (8)−0.0017 (7)0.0098 (7)−0.0041 (7)
C150.0569 (11)0.0437 (10)0.0422 (10)−0.0060 (8)0.0162 (9)−0.0106 (8)
C160.0812 (15)0.0597 (13)0.0383 (11)0.0024 (10)0.0099 (10)0.0188 (9)

Geometric parameters (Å, °)

O1—C31.3652 (17)C4—C51.375 (2)
O1—H10.8200C5—C61.388 (2)
O2—C41.3687 (16)C5—H50.9300
O2—H20.8198C6—H60.9300
O3—C71.2386 (17)C8—C91.466 (2)
O4—C101.3662 (19)C8—H80.9300
O4—C151.4173 (19)C9—C141.383 (2)
O5—C131.3729 (19)C9—C101.404 (2)
O5—C161.4254 (19)C10—C111.383 (2)
O6—H170.8500C11—C121.384 (2)
O6—H180.8508C11—H110.9300
N1—C71.3501 (18)C12—C131.384 (2)
N1—N21.3770 (17)C12—H120.9300
N1—H1A0.8595C13—C141.382 (2)
N2—C81.2740 (19)C14—H140.9300
C1—C61.387 (2)C15—H15A0.9600
C1—C21.396 (2)C15—H15B0.9600
C1—C71.482 (2)C15—H15C0.9600
C2—C31.380 (2)C16—H16A0.9600
C2—H2A0.9300C16—H16B0.9600
C3—C41.399 (2)C16—H16C0.9600
C3—O1—H1109.5C9—C8—H8120.4
C4—O2—H2109.4C14—C9—C10119.21 (14)
C10—O4—C15117.82 (12)C14—C9—C8119.97 (14)
C13—O5—C16117.19 (13)C10—C9—C8120.76 (14)
H17—O6—H18106.2O4—C10—C11124.61 (14)
C7—N1—N2118.09 (12)O4—C10—C9116.64 (13)
C7—N1—H1A120.9C11—C10—C9118.75 (15)
N2—N1—H1A121.0C10—C11—C12121.29 (15)
C8—N2—N1115.64 (13)C10—C11—H11119.4
C6—C1—C2119.12 (13)C12—C11—H11119.4
C6—C1—C7118.53 (13)C11—C12—C13120.12 (14)
C2—C1—C7122.35 (13)C11—C12—H12119.9
C3—C2—C1120.64 (13)C13—C12—H12119.9
C3—C2—H2A119.7O5—C13—C14115.51 (14)
C1—C2—H2A119.7O5—C13—C12125.69 (14)
O1—C3—C2124.19 (13)C14—C13—C12118.78 (15)
O1—C3—C4116.44 (13)C13—C14—C9121.79 (15)
C2—C3—C4119.36 (13)C13—C14—H14119.1
O2—C4—C5119.11 (13)C9—C14—H14119.1
O2—C4—C3120.48 (13)O4—C15—H15A109.5
C5—C4—C3120.41 (13)O4—C15—H15B109.5
C4—C5—C6119.89 (14)H15A—C15—H15B109.5
C4—C5—H5120.1O4—C15—H15C109.5
C6—C5—H5120.1H15A—C15—H15C109.5
C1—C6—C5120.56 (14)H15B—C15—H15C109.5
C1—C6—H6119.7O5—C16—H16A109.5
C5—C6—H6119.7O5—C16—H16B109.5
O3—C7—N1121.84 (13)H16A—C16—H16B109.5
O3—C7—C1122.25 (13)O5—C16—H16C109.5
N1—C7—C1115.91 (12)H16A—C16—H16C109.5
N2—C8—C9119.18 (14)H16B—C16—H16C109.5
N2—C8—H8120.4
C7—N1—N2—C8177.35 (14)N1—N2—C8—C9−176.41 (13)
C6—C1—C2—C3−1.5 (2)N2—C8—C9—C14−0.8 (2)
C7—C1—C2—C3177.70 (13)N2—C8—C9—C10176.25 (15)
C1—C2—C3—O1−179.19 (13)C15—O4—C10—C11−4.8 (2)
C1—C2—C3—C42.0 (2)C15—O4—C10—C9175.43 (14)
O1—C3—C4—O20.1 (2)C14—C9—C10—O4−177.86 (14)
C2—C3—C4—O2179.00 (13)C8—C9—C10—O45.1 (2)
O1—C3—C4—C5179.83 (13)C14—C9—C10—C112.4 (2)
C2—C3—C4—C5−1.2 (2)C8—C9—C10—C11−174.70 (14)
O2—C4—C5—C6179.82 (14)O4—C10—C11—C12179.15 (15)
C3—C4—C5—C60.1 (2)C9—C10—C11—C12−1.1 (2)
C2—C1—C6—C50.3 (2)C10—C11—C12—C13−0.9 (2)
C7—C1—C6—C5−178.94 (14)C16—O5—C13—C14172.04 (16)
C4—C5—C6—C10.4 (2)C16—O5—C13—C12−6.2 (3)
N2—N1—C7—O30.1 (2)C11—C12—C13—O5179.70 (15)
N2—N1—C7—C1179.86 (13)C11—C12—C13—C141.5 (2)
C6—C1—C7—O3−21.2 (2)O5—C13—C14—C9−178.57 (14)
C2—C1—C7—O3159.56 (15)C12—C13—C14—C9−0.2 (2)
C6—C1—C7—N1159.05 (14)C10—C9—C14—C13−1.8 (2)
C2—C1—C7—N1−20.2 (2)C8—C9—C14—C13175.35 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.822.032.8384 (15)168
O2—H2···O10.822.252.7014 (15)115
O2—H2···O5i0.822.433.0191 (15)130
O6—H17···O2ii0.852.062.9003 (15)169
O6—H18···O3i0.851.952.7837 (15)165
N1—H1A···O60.862.162.8592 (17)138

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5111).

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.
  • Pu, X.-H. (2008). Acta Cryst. E64, o1734. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART, SAINT and SADABS Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • 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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