PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o961.
Published online 2008 May 3. doi:  10.1107/S1600536808011768
PMCID: PMC2961356

(2,4-Dimethoxy­benzyl­idene)-2-hydroxy­benzohydrazide ethanol solvate

Abstract

In the planar title mol­ecule, C16H16N2O4·C2H6O, the planar Schiff base molecule is linked to the ethanol solvent mol­ecule by a hydr­oxy–amide hydrogen bond. The hydr­oxy group of the ethanol mol­ecule is a hydrogen-bond donor to the double-bonded N atom of an adjacent Sciff base, pairs of interactions taking place across a center of symmetry and giving rise to a hydrogen-bonded dimer.

Related literature

For the crystal structures of other substituted benzyl­idene-2-hydroxy­benzohydrazides, see: Li (2007 [triangle]); Liang et al. (2005 [triangle]); Luo (2007 [triangle]); Ma et al. (2005 [triangle]); Pan & Yang (2005a [triangle],b [triangle],c [triangle]); Qiu et al. (2006 [triangle]); Shao et al. (2004 [triangle]); Wang et al. (2007 [triangle]); Xu & Liu (2006 [triangle]); Yang (2006 [triangle]); Yang & Pan (2004 [triangle], 2005a [triangle],b [triangle]); Zhang et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o961-scheme1.jpg

Experimental

Crystal data

  • C16H16N2O4·C2H6O
  • M r = 346.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o961-efi1.jpg
  • a = 7.7909 (2) Å
  • b = 18.0539 (6) Å
  • c = 12.0001 (4) Å
  • β = 93.803 (2)°
  • V = 1684.17 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 (2) K
  • 0.20 × 0.15 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 13796 measured reflections
  • 3853 independent reflections
  • 2575 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.118
  • S = 1.03
  • 3853 reflections
  • 241 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011768/sg2239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011768/sg2239Isup2.hkl

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

Acknowledgments

We acknowledge the SAGA grant (06–02-03–0147) for support of this study, and the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

The crystal structures of a number of substituted benzylidene-2-hydroxybenzohydrazides have been reported (Li, 2007; Liang et al., 2005; Luo, 2007; Ma et al., 2005; Pan & Yang, 2005a,b,c; Qiu et al., 2006; Shao et al., 2004; Wang et al., 2007; Xu & Liu, 2006; Yang, 2006; Yang & Pan, 2004, 2005a,b; Zhang et al., 2006.

The 2,4-dimethoxy derivative crystallizes as an ethanol solvate (Scheme I, Fig. 1). The planar molecule of C16H16N2O4 is linked to the ethanol molecule by an amido···hydroxyethanol hydrogen bond [N–H···O 2.894 (2) Å]. The hydroxy unit of the ethanol molecule is a hydrogen-bond donor site to the double-bond nitrogen atom of an adjacent Sciff base [O–H···N 2.847 (2) Å], this interaction across a center of symmetry giving rise to a hydrogen-bonded dimer (Fig. 2).

Experimental

2-Hydroxybenzohydrazide (0.60 g, 4 mmol) and 2,4-dimethoxybenzaldehyde (0.66 g, 4 mmol) were heated in ethanol (30 ml) for 2 h. The solvent was removed by evaporation and the product recrystallized from ethanol.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5 U(C).

The oxygen- and nitrogen-bound H-atoms were located in a difference Fouier map, and were refined with a distance restraint (O–H = N–H 0.85 Å); their temperature factors were freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C16H16N2O4.C2H6O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.
Fig. 2.
Hydrogen-bonded dimeric structure.

Crystal data

C16H16N2O4·C2H6OF000 = 736
Mr = 346.38Dx = 1.366 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1895 reflections
a = 7.7909 (2) Åθ = 2.8–25.5º
b = 18.0539 (6) ŵ = 0.10 mm1
c = 12.0001 (4) ÅT = 100 (2) K
β = 93.803 (2)ºPrism, colorless
V = 1684.17 (9) Å30.20 × 0.15 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer2575 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 2.0º
ω scansh = −10→10
Absorption correction: Nonek = −20→23
13796 measured reflectionsl = −15→15
3853 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118  w = 1/[σ2(Fo2) + (0.0476P)2 + 0.175P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3853 reflectionsΔρmax = 0.21 e Å3
241 parametersΔρmin = −0.24 e Å3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.64682 (15)0.22307 (7)0.69448 (11)0.0248 (3)
O20.48542 (15)0.30514 (7)0.55256 (10)0.0253 (3)
O30.09164 (14)0.62457 (7)0.44328 (10)0.0224 (3)
O4−0.15888 (16)0.55131 (7)0.07909 (10)0.0280 (3)
O50.45339 (16)0.56902 (7)0.68732 (11)0.0256 (3)
N10.40917 (17)0.42200 (9)0.59366 (12)0.0191 (3)
N20.32044 (17)0.42928 (8)0.48948 (11)0.0195 (3)
C10.6546 (2)0.28297 (10)0.76338 (14)0.0199 (4)
C20.7381 (2)0.27412 (10)0.86870 (14)0.0219 (4)
H20.78580.22750.89040.026*
C30.7514 (2)0.33316 (11)0.94120 (14)0.0231 (4)
H30.80730.32661.01330.028*
C40.6847 (2)0.40220 (10)0.91101 (14)0.0230 (4)
H40.69620.44280.96140.028*
C50.6014 (2)0.41094 (10)0.80671 (14)0.0211 (4)
H50.55600.45810.78560.025*
C60.5825 (2)0.35172 (10)0.73132 (14)0.0180 (4)
C70.4908 (2)0.35796 (10)0.61929 (14)0.0192 (4)
C80.22902 (19)0.48872 (10)0.47864 (14)0.0188 (4)
H80.22770.52260.53910.023*
C90.1282 (2)0.50446 (10)0.37526 (14)0.0185 (4)
C100.0552 (2)0.57510 (10)0.35888 (14)0.0189 (4)
C11−0.0433 (2)0.59274 (10)0.26156 (14)0.0197 (4)
H11−0.09300.64050.25190.024*
C12−0.0677 (2)0.53942 (10)0.17899 (14)0.0213 (4)
C130.0016 (2)0.46857 (10)0.19353 (15)0.0227 (4)
H13−0.01730.43210.13690.027*
C140.0973 (2)0.45200 (10)0.29057 (14)0.0205 (4)
H140.14380.40360.30040.025*
C150.0125 (2)0.69592 (10)0.43449 (15)0.0240 (4)
H15A0.04560.72500.50150.036*
H15B−0.11280.69020.42750.036*
H15C0.05050.72150.36850.036*
C16−0.2167 (2)0.62483 (11)0.05390 (16)0.0281 (4)
H16A−0.27070.6264−0.02220.042*
H16B−0.11840.65880.05970.042*
H16C−0.30060.63980.10690.042*
C170.4115 (2)0.62589 (11)0.76362 (15)0.0278 (4)
H17A0.51860.65060.79290.033*
H17B0.35670.60330.82750.033*
C180.2921 (2)0.68255 (11)0.70951 (16)0.0310 (5)
H18A0.26080.71870.76550.046*
H18B0.18810.65790.67750.046*
H18C0.34960.70790.65020.046*
H1O0.594 (3)0.2375 (13)0.6331 (12)0.054 (7)*
H5O0.518 (2)0.5858 (13)0.6389 (15)0.052 (7)*
H1N0.410 (3)0.4596 (8)0.6371 (14)0.036 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0311 (7)0.0185 (7)0.0241 (7)0.0015 (5)−0.0021 (6)−0.0001 (6)
O20.0328 (7)0.0185 (7)0.0236 (7)0.0024 (5)−0.0045 (5)−0.0035 (6)
O30.0291 (6)0.0170 (7)0.0208 (7)0.0034 (5)−0.0009 (5)−0.0022 (5)
O40.0342 (7)0.0261 (8)0.0225 (7)0.0032 (6)−0.0077 (5)0.0004 (6)
O50.0313 (7)0.0212 (7)0.0247 (7)0.0003 (6)0.0063 (6)−0.0036 (6)
N10.0227 (7)0.0181 (8)0.0163 (8)−0.0002 (6)−0.0007 (6)−0.0006 (7)
N20.0206 (7)0.0205 (8)0.0169 (8)−0.0006 (6)−0.0012 (6)0.0010 (7)
C10.0190 (8)0.0193 (10)0.0218 (9)−0.0023 (7)0.0033 (7)−0.0003 (8)
C20.0212 (8)0.0210 (10)0.0233 (10)0.0009 (7)0.0000 (7)0.0044 (8)
C30.0224 (8)0.0285 (11)0.0183 (9)−0.0043 (8)0.0001 (7)0.0050 (8)
C40.0263 (9)0.0235 (10)0.0194 (9)−0.0042 (7)0.0031 (7)−0.0034 (8)
C50.0221 (8)0.0181 (10)0.0232 (10)−0.0003 (7)0.0022 (7)0.0017 (8)
C60.0192 (8)0.0169 (10)0.0181 (9)−0.0020 (7)0.0018 (6)0.0009 (7)
C70.0187 (8)0.0176 (10)0.0214 (9)−0.0012 (7)0.0024 (7)−0.0001 (8)
C80.0190 (8)0.0181 (9)0.0198 (9)−0.0010 (7)0.0044 (7)0.0001 (8)
C90.0191 (8)0.0187 (9)0.0179 (9)−0.0014 (7)0.0032 (6)0.0005 (8)
C100.0181 (8)0.0193 (10)0.0196 (9)−0.0026 (7)0.0043 (7)−0.0026 (8)
C110.0195 (8)0.0179 (10)0.0218 (9)0.0012 (7)0.0027 (7)0.0028 (8)
C120.0210 (8)0.0228 (10)0.0200 (9)−0.0026 (7)0.0009 (7)0.0018 (8)
C130.0253 (9)0.0206 (10)0.0218 (10)−0.0024 (7)−0.0006 (7)−0.0034 (8)
C140.0217 (8)0.0158 (9)0.0240 (10)−0.0014 (7)0.0023 (7)0.0007 (8)
C150.0268 (9)0.0187 (10)0.0267 (10)0.0036 (7)0.0032 (7)−0.0032 (8)
C160.0288 (9)0.0294 (11)0.0254 (10)0.0027 (8)−0.0031 (8)0.0047 (9)
C170.0319 (10)0.0270 (11)0.0245 (10)0.0004 (8)0.0026 (8)−0.0066 (9)
C180.0323 (10)0.0270 (12)0.0339 (11)0.0002 (8)0.0040 (8)−0.0023 (9)

Geometric parameters (Å, °)

O1—C11.360 (2)C8—C91.452 (2)
O1—H1O0.859 (9)C8—H80.9500
O2—C71.244 (2)C9—C141.398 (2)
O3—C101.366 (2)C9—C101.405 (2)
O3—C151.429 (2)C10—C111.391 (2)
O4—C121.369 (2)C11—C121.385 (2)
O4—C161.428 (2)C11—H110.9500
O5—C171.428 (2)C12—C131.395 (2)
O5—H5O0.848 (10)C13—C141.374 (2)
N1—C71.345 (2)C13—H130.9500
N1—N21.3941 (19)C14—H140.9500
N1—H1N0.855 (9)C15—H15A0.9800
N2—C81.290 (2)C15—H15B0.9800
C1—C21.392 (2)C15—H15C0.9800
C1—C61.405 (2)C16—H16A0.9800
C2—C31.375 (2)C16—H16B0.9800
C2—H20.9500C16—H16C0.9800
C3—C41.389 (3)C17—C181.501 (3)
C3—H30.9500C17—H17A0.9900
C4—C51.380 (2)C17—H17B0.9900
C4—H40.9500C18—H18A0.9800
C5—C61.402 (2)C18—H18B0.9800
C5—H50.9500C18—H18C0.9800
C6—C71.485 (2)
C1—O1—H1O106.2 (16)C11—C10—C9121.39 (16)
C10—O3—C15117.86 (13)C12—C11—C10118.89 (16)
C12—O4—C16117.97 (14)C12—C11—H11120.6
C17—O5—H5O110.7 (17)C10—C11—H11120.6
C7—N1—N2119.00 (15)O4—C12—C11123.77 (16)
C7—N1—H1N123.9 (14)O4—C12—C13115.29 (16)
N2—N1—H1N117.1 (14)C11—C12—C13120.94 (16)
C8—N2—N1113.99 (14)C14—C13—C12119.31 (17)
O1—C1—C2117.39 (16)C14—C13—H13120.3
O1—C1—C6122.35 (15)C12—C13—H13120.3
C2—C1—C6120.27 (16)C13—C14—C9121.74 (17)
C3—C2—C1119.77 (17)C13—C14—H14119.1
C3—C2—H2120.1C9—C14—H14119.1
C1—C2—H2120.1O3—C15—H15A109.5
C2—C3—C4121.28 (16)O3—C15—H15B109.5
C2—C3—H3119.4H15A—C15—H15B109.5
C4—C3—H3119.4O3—C15—H15C109.5
C5—C4—C3118.97 (17)H15A—C15—H15C109.5
C5—C4—H4120.5H15B—C15—H15C109.5
C3—C4—H4120.5O4—C16—H16A109.5
C4—C5—C6121.40 (17)O4—C16—H16B109.5
C4—C5—H5119.3H16A—C16—H16B109.5
C6—C5—H5119.3O4—C16—H16C109.5
C5—C6—C1118.29 (15)H16A—C16—H16C109.5
C5—C6—C7123.38 (16)H16B—C16—H16C109.5
C1—C6—C7118.32 (15)O5—C17—C18111.97 (15)
O2—C7—N1121.10 (16)O5—C17—H17A109.2
O2—C7—C6121.22 (15)C18—C17—H17A109.2
N1—C7—C6117.66 (15)O5—C17—H17B109.2
N2—C8—C9120.86 (16)C18—C17—H17B109.2
N2—C8—H8119.6H17A—C17—H17B107.9
C9—C8—H8119.6C17—C18—H18A109.5
C14—C9—C10117.70 (15)C17—C18—H18B109.5
C14—C9—C8123.06 (16)H18A—C18—H18B109.5
C10—C9—C8119.23 (16)C17—C18—H18C109.5
O3—C10—C11123.27 (16)H18A—C18—H18C109.5
O3—C10—C9115.32 (15)H18B—C18—H18C109.5
C7—N1—N2—C8171.60 (15)N2—C8—C9—C1412.2 (2)
O1—C1—C2—C3179.24 (15)N2—C8—C9—C10−168.70 (15)
C6—C1—C2—C3−0.6 (2)C15—O3—C10—C115.3 (2)
C1—C2—C3—C4−0.8 (2)C15—O3—C10—C9−176.25 (14)
C2—C3—C4—C51.0 (2)C14—C9—C10—O3−178.97 (14)
C3—C4—C5—C60.2 (2)C8—C9—C10—O31.9 (2)
C4—C5—C6—C1−1.6 (2)C14—C9—C10—C11−0.5 (2)
C4—C5—C6—C7178.61 (15)C8—C9—C10—C11−179.61 (15)
O1—C1—C6—C5−178.08 (14)O3—C10—C11—C12177.63 (14)
C2—C1—C6—C51.7 (2)C9—C10—C11—C12−0.7 (2)
O1—C1—C6—C71.8 (2)C16—O4—C12—C116.8 (2)
C2—C1—C6—C7−178.44 (14)C16—O4—C12—C13−173.16 (15)
N2—N1—C7—O2−1.3 (2)C10—C11—C12—O4−178.49 (15)
N2—N1—C7—C6−179.38 (13)C10—C11—C12—C131.5 (2)
C5—C6—C7—O2175.88 (16)O4—C12—C13—C14179.01 (14)
C1—C6—C7—O2−4.0 (2)C11—C12—C13—C14−0.9 (3)
C5—C6—C7—N1−6.1 (2)C12—C13—C14—C9−0.3 (3)
C1—C6—C7—N1174.10 (15)C10—C9—C14—C131.0 (2)
N1—N2—C8—C9−179.75 (14)C8—C9—C14—C13−179.89 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···O20.86 (1)1.74 (2)2.528 (2)151 (2)
O5—H5o···N2i0.85 (1)2.07 (1)2.847 (2)152 (2)
N1—H1n···O50.86 (1)2.09 (1)2.894 (2)157 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2239).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, W.-H. (2007). Acta Cryst. E63, o2136–o2137.
  • Liang, H.-D., Yang, J.-G., Yang, H. & Pan, F.-Y. (2005). Z. Kristallogr. New Cryst. Struct 220, 585–586.
  • Luo, Z.-G. (2007). Acta Cryst. E63, o3672.
  • Ma, J., Zhang, S.-P., Sheng, L.-Q., Fan, M., Yang, Y.-L. & Shao, S.-C. (2005). Acta Cryst. E61, o1747–o1748.
  • Pan, F.-Y. & Yang, J.-G. (2005a). Acta Cryst. E61, o354–o355.
  • Pan, F.-Y. & Yang, J.-G. (2005b). Z. Kristallogr. New Cryst. Struct.220, 515–516.
  • Pan, F.-Y. & Yang, J.-G. (2005c). Z. Kristallogr. New Cryst. Struct.220, 517–518.
  • Qiu, X.-Y., Luo, Z.-G., Yang, S.-L. & Liu, W.-S. (2006). Acta Cryst. E62, o3531–o3532.
  • Shao, S.-C., You, Z.-L., Xiong, Z.-D., Chen, B. & Zhu, H.-L. (2004). Acta Cryst. E60, o2187–o2188.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, N., Li, J.-P. & Pu, Y. L. (2007). Chin. J. Struct. Chem.26, 547–550.
  • Westrip, S. P. (2008). publCIF In preparation.
  • Xu, H.-M. & Liu, S.-X. (2006). Acta Cryst. E62, o3026–o3027.
  • Yang, D.-S. (2006). Acta Cryst. E62, o1591–o1592.
  • Yang, J.-G. & Pan, F.-Y. (2004). Acta Cryst. E60, o2009–o2010.
  • Yang, J.-G. & Pan, F.-Y. (2005a). Acta Cryst. E61, o1038–o1040.
  • Yang, J.-G. & Pan, F.-Y. (2005b). Acta Cryst. E61, o831–o832.
  • Zhang, Y., Zhang, S.-P., Wu, Y.-Y. & Shao, S.-C. (2006). Acta Cryst. E62, o119–o120.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography