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Acta Cryst. (2008). E64, o961    [ doi:10.1107/S1600536808011768 ]

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

W. A. Yehye, A. Ariffin and S. W. Ng

Abstract top

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.

Comment top

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).

Related literature top

The crystal structures of other substituted benzylidene-2-hydroxybenzohydrazides have been reported; see: 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).

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C16H16N2O4.C2H6O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.
[Figure 2] Fig. 2. Hydrogen-bonded dimeric structure.
(2,4-Dimethoxybenzylidene)-2-hydroxybenzohydrazide ethanol solvate top
Crystal data top
C16H16N2O4·C2H6OF000 = 736
Mr = 346.38Dx = 1.366 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		2575 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 top
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 Å−3
241 parametersΔρmin = −0.24 e Å−3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C16H16N2O4·C2H6OV = 1684.17 (9) Å3
Mr = 346.38Z = 4
Monoclinic, P21/nMo Kα
a = 7.7909 (2) ŵ = 0.10 mm−1
b = 18.0539 (6) ÅT = 100 (2) K
c = 12.0001 (4) Å0.20 × 0.15 × 0.15 mm
β = 93.803 (2)º
Data collection top
Bruker SMART APEX
diffractometer		3853 independent reflections
Absorption correction: None2575 reflections with I > 2σ(I)
13796 measured reflectionsRint = 0.059
Refinement top
R[F2 > 2σ(F2)] = 0.0463 restraints
wR(F2) = 0.118H atoms treated by a mixture of
independent and constrained refinement
S = 1.03Δρmax = 0.21 e Å−3
3853 reflectionsΔρmin = −0.24 e Å−3
241 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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.

references
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