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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1373.
Published online 2009 May 23. doi:  10.1107/S1600536809018947
PMCID: PMC2969598

N′-(2,4-Dimethoxy­benzyl­idene)-3,4,5-trihydroxy­benzohydrazide ethanol solvate

Abstract

The title compound, C16H16N2O6·C2H5OH, was synthesized from 3,4,5-trihydroxy­benzoyl­hydrazide and 2,4-dimethoxy­benzaldehyde in ethanol. The compound is not planar, with the two aromatic planes of the two aromatic rings twisted by 15.6 (1)°. The hydr­oxy groups are involved in both intra­molecular O—H(...)O and inter­molecular O—H(...)N and O—H(...)O hydrogen bonds and a C—H(...)O interaction also occurs.

Related literature

For related compounds, see Abdul Alhadi et al. (2009 [triangle]). For the parent N′-(2-hydroxy­benzyl­idene)benzohydrazide, see Lyubchova et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1373-scheme1.jpg

Experimental

Crystal data

  • C16H16N2O6·C2H6O
  • M r = 378.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1373-efi1.jpg
  • a = 7.8347 (1) Å
  • b = 17.5412 (3) Å
  • c = 13.0230 (2) Å
  • β = 93.936 (1)°
  • V = 1785.53 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 K
  • 0.31 × 0.16 × 0.12 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.967, T max = 0.987
  • 19580 measured reflections
  • 5188 independent reflections
  • 3586 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.121
  • S = 1.02
  • 5188 reflections
  • 253 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.27 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 I, global. DOI: 10.1107/S1600536809018947/hg2510sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018947/hg2510Isup2.hkl

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

Acknowledgments

The authors thank the University of Malaya for funding this study (Science Fund Grant 12-0-03-2031, 12-02-03-2051 and PJP FS350-2008)

supplementary crystallographic information

Experimental

A mixture of 3,4,5-trihydroxybenzoylhydrazide and 2,4-dimethoxybenzaldehyde were heated in ethanol (50 ml) for 12 h. The yellow crystals were obtained by recrystallization from ethanol.

Refinement

All H atoms were placed at calculated positions (C— H 0.95 - 0.99, N—H 0.88, and O—H 0.84 Å) with Uiso(H) set to 1.2 - 1.5times Ueq (C,N,O)

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C16H16N2O6.C2H5OH at 70% probability level. Hydrogen atoms are drawn as sphere of arbitrary radius.

Crystal data

C16H16N2O6·C2H6OF(000) = 800
Mr = 378.38Dx = 1.408 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3445 reflections
a = 7.8347 (1) Åθ = 2.8–29.1°
b = 17.5412 (3) ŵ = 0.11 mm1
c = 13.0230 (2) ÅT = 100 K
β = 93.936 (1)°Block, yellow
V = 1785.53 (5) Å30.31 × 0.16 × 0.12 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer5188 independent reflections
Radiation source: fine-focus sealed tube3586 reflections with I > 2σ(I)
graphiteRint = 0.041
ω scansθmax = 30.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→10
Tmin = 0.967, Tmax = 0.987k = −24→24
19580 measured reflectionsl = −18→18

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0566P)2 + 0.3538P] where P = (Fo2 + 2Fc2)/3
5188 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.26 e Å3

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
C11.15941 (17)0.21466 (7)0.76768 (10)0.0156 (3)
H11.14580.25830.72480.019*
C21.25203 (17)0.22016 (7)0.86245 (10)0.0153 (3)
C31.26837 (17)0.15678 (8)0.92716 (10)0.0154 (3)
C41.19696 (18)0.08744 (8)0.89317 (10)0.0170 (3)
C51.10756 (18)0.08150 (8)0.79830 (10)0.0176 (3)
H51.06050.03390.77600.021*
C61.08672 (17)0.14571 (7)0.73529 (10)0.0154 (3)
C70.98683 (17)0.14395 (8)0.63409 (10)0.0159 (3)
C80.74521 (17)0.00842 (8)0.49550 (10)0.0168 (3)
H80.7539−0.02960.54760.023 (4)*
C90.64100 (17)−0.00596 (8)0.40063 (10)0.0165 (3)
C100.57036 (17)−0.07846 (8)0.38154 (10)0.0163 (3)
C110.47202 (17)−0.09404 (8)0.29061 (10)0.0172 (3)
H110.4236−0.14310.27850.021*
C120.44633 (18)−0.03640 (8)0.21828 (11)0.0188 (3)
C130.51352 (19)0.03637 (8)0.23587 (11)0.0209 (3)
H130.49390.07540.18590.025*
C140.60860 (18)0.05093 (8)0.32640 (11)0.0190 (3)
H140.65330.10070.33890.023*
C150.2879 (2)−0.11915 (8)0.09897 (11)0.0227 (3)
H15A0.3824−0.15570.09780.034*
H15B0.2270−0.11690.03070.034*
H15C0.2087−0.13540.14980.034*
C160.5321 (2)−0.20516 (8)0.44383 (12)0.0247 (3)
H16A0.4072−0.20070.43580.037*
H16B0.5647−0.23640.50440.037*
H16C0.5737−0.22920.38240.037*
C170.7901 (2)0.81507 (9)0.72385 (14)0.0313 (4)
H19A0.69290.83700.68260.047*
H19B0.74820.78660.78180.047*
H19C0.85310.78060.68090.047*
C180.9073 (2)0.87827 (9)0.76416 (12)0.0259 (3)
H18A0.84580.91100.81130.031*
H18B1.00740.85590.80380.031*
N10.92094 (15)0.07647 (6)0.60343 (9)0.0168 (2)
H1'0.93790.03570.64220.030 (5)*
N20.82556 (15)0.07168 (6)0.50974 (9)0.0174 (2)
O10.96209 (13)0.20261 (5)0.58110 (7)0.0219 (2)
O21.32670 (14)0.28879 (5)0.88620 (7)0.0218 (2)
H21.35690.29010.94930.033*
O31.35316 (13)0.15568 (6)1.02261 (7)0.0209 (2)
H31.38770.19981.03810.031*
O41.21299 (15)0.02350 (6)0.95174 (8)0.0273 (3)
H41.27180.03321.00650.041*
O50.60584 (13)−0.13118 (6)0.45673 (7)0.0224 (2)
O60.35424 (14)−0.04532 (6)0.12604 (8)0.0264 (3)
O70.96498 (14)0.92367 (6)0.68270 (8)0.0229 (2)
H71.02910.89750.64750.034*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0190 (6)0.0138 (6)0.0137 (6)0.0025 (5)−0.0015 (5)0.0010 (5)
C20.0187 (6)0.0123 (6)0.0148 (6)−0.0006 (5)0.0000 (5)−0.0015 (5)
C30.0175 (6)0.0163 (6)0.0119 (6)0.0006 (5)−0.0021 (5)−0.0010 (5)
C40.0214 (7)0.0143 (6)0.0147 (6)0.0000 (5)−0.0029 (5)0.0027 (5)
C50.0223 (7)0.0140 (6)0.0159 (7)−0.0007 (5)−0.0034 (5)−0.0003 (5)
C60.0171 (6)0.0156 (6)0.0131 (6)0.0011 (5)−0.0020 (5)−0.0006 (5)
C70.0175 (6)0.0157 (6)0.0141 (6)0.0019 (5)−0.0016 (5)−0.0005 (5)
C80.0194 (7)0.0158 (6)0.0148 (6)0.0008 (5)−0.0021 (5)0.0007 (5)
C90.0170 (6)0.0168 (6)0.0151 (7)−0.0002 (5)−0.0021 (5)−0.0009 (5)
C100.0187 (7)0.0162 (6)0.0139 (6)0.0010 (5)−0.0010 (5)0.0013 (5)
C110.0188 (7)0.0162 (6)0.0161 (6)−0.0014 (5)−0.0020 (5)−0.0015 (5)
C120.0201 (7)0.0192 (7)0.0162 (7)0.0000 (5)−0.0059 (5)−0.0012 (5)
C130.0274 (8)0.0156 (6)0.0186 (7)−0.0001 (6)−0.0065 (6)0.0026 (5)
C140.0208 (7)0.0141 (6)0.0212 (7)−0.0009 (5)−0.0040 (5)−0.0008 (5)
C150.0287 (8)0.0186 (7)0.0197 (7)−0.0034 (6)−0.0074 (6)−0.0025 (6)
C160.0339 (8)0.0158 (7)0.0236 (8)−0.0045 (6)−0.0042 (6)0.0033 (6)
C170.0369 (9)0.0197 (7)0.0381 (10)−0.0044 (7)0.0079 (7)−0.0009 (7)
C180.0344 (8)0.0217 (7)0.0212 (7)0.0002 (6)−0.0020 (6)0.0049 (6)
N10.0215 (6)0.0151 (5)0.0129 (5)−0.0010 (4)−0.0063 (4)0.0013 (4)
N20.0199 (6)0.0172 (6)0.0142 (6)0.0000 (5)−0.0064 (4)−0.0011 (4)
O10.0323 (6)0.0142 (5)0.0176 (5)0.0012 (4)−0.0101 (4)0.0016 (4)
O20.0353 (6)0.0145 (5)0.0145 (5)−0.0057 (4)−0.0070 (4)0.0012 (4)
O30.0310 (6)0.0167 (5)0.0137 (5)−0.0028 (4)−0.0079 (4)0.0011 (4)
O40.0446 (7)0.0167 (5)0.0184 (5)−0.0065 (5)−0.0141 (5)0.0056 (4)
O50.0320 (6)0.0162 (5)0.0177 (5)−0.0042 (4)−0.0076 (4)0.0030 (4)
O60.0382 (6)0.0176 (5)0.0209 (5)−0.0043 (4)−0.0160 (5)0.0010 (4)
O70.0295 (6)0.0163 (5)0.0232 (6)0.0001 (4)0.0034 (4)−0.0001 (4)

Geometric parameters (Å, °)

C1—C61.3900 (18)C13—C141.3745 (19)
C1—C21.3914 (18)C13—H130.9500
C1—H10.9500C14—H140.9500
C2—O21.3647 (15)C15—O61.4308 (16)
C2—C31.3958 (18)C15—H15A0.9800
C3—O31.3687 (15)C15—H15B0.9800
C3—C41.3979 (18)C15—H15C0.9800
C4—O41.3574 (16)C16—O51.4258 (17)
C4—C51.3818 (18)C16—H16A0.9800
C5—C61.3965 (18)C16—H16B0.9800
C5—H50.9500C16—H16C0.9800
C6—C71.4862 (18)C17—C181.511 (2)
C7—O11.2466 (16)C17—H19A0.9800
C7—N11.3412 (17)C17—H19B0.9800
C8—N21.2830 (17)C17—H19C0.9800
C8—C91.4554 (18)C18—O71.4247 (18)
C8—H80.9500C18—H18A0.9900
C9—C141.4004 (19)C18—H18B0.9900
C9—C101.4023 (18)N1—N21.3889 (15)
C10—O51.3615 (16)N1—H1'0.8800
C10—C111.3948 (18)O2—H20.8400
C11—C121.3869 (19)O3—H30.8400
C11—H110.9500O4—H40.8400
C12—O61.3672 (16)O7—H70.8400
C12—C131.3938 (19)
C6—C1—C2120.50 (12)C12—C13—H13120.4
C6—C1—H1119.8C13—C14—C9121.44 (13)
C2—C1—H1119.8C13—C14—H14119.3
O2—C2—C1116.85 (12)C9—C14—H14119.3
O2—C2—C3123.07 (11)O6—C15—H15A109.5
C1—C2—C3120.06 (12)O6—C15—H15B109.5
O3—C3—C2125.32 (12)H15A—C15—H15B109.5
O3—C3—C4115.73 (11)O6—C15—H15C109.5
C2—C3—C4118.93 (11)H15A—C15—H15C109.5
O4—C4—C5117.51 (12)H15B—C15—H15C109.5
O4—C4—C3121.43 (12)O5—C16—H16A109.5
C5—C4—C3121.07 (12)O5—C16—H16B109.5
C4—C5—C6119.75 (12)H16A—C16—H16B109.5
C4—C5—H5120.1O5—C16—H16C109.5
C6—C5—H5120.1H16A—C16—H16C109.5
C1—C6—C5119.63 (12)H16B—C16—H16C109.5
C1—C6—C7117.84 (11)C18—C17—H19A109.5
C5—C6—C7122.52 (12)C18—C17—H19B109.5
O1—C7—N1121.44 (12)H19A—C17—H19B109.5
O1—C7—C6121.75 (12)C18—C17—H19C109.5
N1—C7—C6116.79 (12)H19A—C17—H19C109.5
N2—C8—C9120.91 (12)H19B—C17—H19C109.5
N2—C8—H8119.5O7—C18—C17111.58 (13)
C9—C8—H8119.5O7—C18—H18A109.3
C14—C9—C10118.24 (12)C17—C18—H18A109.3
C14—C9—C8121.81 (12)O7—C18—H18B109.3
C10—C9—C8119.95 (12)C17—C18—H18B109.3
O5—C10—C11123.45 (12)H18A—C18—H18B108.0
O5—C10—C9115.45 (11)C7—N1—N2119.19 (11)
C11—C10—C9121.09 (12)C7—N1—H1'120.4
C12—C11—C10118.67 (12)N2—N1—H1'120.4
C12—C11—H11120.7C8—N2—N1114.10 (11)
C10—C11—H11120.7C2—O2—H2109.5
O6—C12—C11123.82 (12)C3—O3—H3109.5
O6—C12—C13114.82 (12)C4—O4—H4109.5
C11—C12—C13121.36 (12)C10—O5—C16118.18 (11)
C14—C13—C12119.17 (13)C12—O6—C15118.75 (11)
C14—C13—H13120.4C18—O7—H7109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O30.842.542.9325 (13)109
O3—H3···O20.842.542.9325 (13)110
O4—H4···O30.842.252.7009 (14)114
N1—H1'···O7i0.882.042.8844 (15)160
O2—H2···O1ii0.841.862.6871 (13)170
O2—H2···N2ii0.842.572.9293 (15)107
O3—H3···O1ii0.841.882.7200 (13)177
O4—H4···O6iii0.842.142.7366 (14)127
C14—H14···O2iv0.952.423.3539 (17)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2510).

References

  • Abdul Alhadi, A. A., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o909. [PMC free article] [PubMed]
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Lyubchova, A., Cossé-Barbi, A., Doucet, J. P., Robert, F., Souron, J.-P. & Quarton, M. (1995). Acta Cryst. C51, 1893–1895.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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