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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o910.
Published online 2009 March 28. doi:  10.1107/S1600536809010812
PMCID: PMC2968776

N′-(5-Chloro-2-hydroxy­benzyl­idene)-3,4,5-trihydroxy­benzohydrazide dihydrate

Abstract

The benzohydrazide mol­ecule in the title dihydrate, C14H11ClN2O5·2H2O, is non-planar, with the two aromatic rings at either side of the –C(=O)—NH—N=CH– unit forming a dihedral angle of 29.7 (2)°. The benzohydrazide mol­ecule is linked to the water mol­ecules by O—H(...)O and N—H(...)O hydrogen bonds, with other O—H(...)O hydrogen bonds leading to a layer structure.

Related literature

For the the parent N′-(2-hydroxy­benzyl­idene)benzohydrazide, see: Lyubchova et al. (1995 [triangle]). For other N′-(2-hydr­oxy-5-nitro­benzyl­idene)benzohydrazides, see: Ali et al. (2005 [triangle]); Lyubchova et al. (1995 [triangle]); Xu & Liu (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o910-scheme1.jpg

Experimental

Crystal data

  • C14H11ClN2O5·2H2O
  • M r = 358.73
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o910-efi1.jpg
  • a = 30.5627 (12) Å
  • b = 3.7539 (2) Å
  • c = 12.8882 (5) Å
  • β = 90.450 (3)°
  • V = 1478.61 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 100 K
  • 0.36 × 0.04 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.899, T max = 0.988
  • 10104 measured reflections
  • 2623 independent reflections
  • 1801 reflections with I > 2σ(I)
  • R int = 0.097

Refinement

  • R[F 2 > 2σ(F 2)] = 0.071
  • wR(F 2) = 0.181
  • S = 1.07
  • 2623 reflections
  • 221 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010812/tk2403sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010812/tk2403Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

5-Chloro-2-hydroxybenzaldehyde (0.31 g, 2 mmol) and 3,4,5-trihydroxybenzoylhydrazide (0.36 g, 2 mmol) were heated in ethanol (50 ml) for several hours. The solvent was removed and the product recrystallized from DMSO.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 Å, U(H) = 1.2U(C)], and were included in the refinement in the riding model approximation. The amino (0.88 Å) and hydroxy H-atoms (0.84 Å) were similarly generated with Uiso = 1.2Ueq(carrier atom) for N-H and Uiso = 1.5Ueq(carrier atom) for O-H. The water H-atoms were placed in chemically sensible positions on the basis of possible hydrogen bonds, but were not refined; Uiso = 1.5Ueq(O).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C14H11ClN2O5.2H2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C14H11ClN2O5·2H2OF(000) = 744
Mr = 358.73Dx = 1.611 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1505 reflections
a = 30.5627 (12) Åθ = 2.7–24.3°
b = 3.7539 (2) ŵ = 0.30 mm1
c = 12.8882 (5) ÅT = 100 K
β = 90.450 (3)°Prism, yellow
V = 1478.61 (11) Å30.36 × 0.04 × 0.04 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer2623 independent reflections
Radiation source: fine-focus sealed tube1801 reflections with I > 2σ(I)
graphiteRint = 0.097
ω scansθmax = 25.0°, θmin = 0.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −36→36
Tmin = 0.899, Tmax = 0.988k = −4→4
10104 measured reflectionsl = −15→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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0537P)2 + 5.5995P] where P = (Fo2 + 2Fc2)/3
2623 reflections(Δ/σ)max = 0.001
221 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.49 e Å3

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

xyzUiso*/Ueq
Cl10.53161 (4)0.3168 (4)0.59750 (10)0.0244 (3)
O10.67086 (11)0.6471 (10)0.8994 (2)0.0243 (9)
H10.69330.72360.86940.036*
O20.79657 (11)0.9733 (10)0.8420 (2)0.0232 (9)
O30.94472 (12)1.3696 (12)0.7043 (3)0.0349 (10)
H30.96631.32790.66610.052*
O40.94729 (12)1.0933 (13)0.5106 (3)0.0395 (12)
H40.94810.93320.46510.059*
O50.87480 (11)0.7706 (11)0.4244 (2)0.0245 (9)
H50.84980.71910.40130.037*
O1w0.97110 (13)0.8480 (13)0.8663 (4)0.0542 (14)
H110.96760.90370.80400.081*
H120.96661.02530.90420.081*
O2w0.73755 (11)0.1847 (10)0.9961 (2)0.0239 (8)
H210.71410.26330.97000.036*
H220.75540.14380.94820.036*
N10.71793 (13)0.8677 (12)0.7419 (3)0.0194 (10)
N20.75565 (13)0.9864 (12)0.6939 (3)0.0187 (9)
H20.75451.05290.62840.022*
C10.63896 (16)0.5781 (13)0.8275 (4)0.0179 (11)
C20.60017 (17)0.4266 (14)0.8603 (4)0.0209 (12)
H2A0.59650.37400.93180.025*
C30.56699 (17)0.3513 (14)0.7916 (4)0.0233 (12)
H3A0.54030.25080.81510.028*
C40.57295 (16)0.4243 (13)0.6865 (4)0.0189 (11)
C50.61125 (16)0.5725 (13)0.6514 (4)0.0193 (11)
H5A0.61480.62130.57970.023*
C60.64514 (16)0.6516 (14)0.7219 (4)0.0179 (11)
C70.68550 (15)0.7976 (13)0.6815 (4)0.0172 (11)
H70.68800.84210.60920.021*
C90.79416 (16)1.0018 (14)0.7457 (4)0.0181 (11)
C100.83308 (16)1.0434 (14)0.6800 (4)0.0183 (11)
C110.87050 (16)1.1993 (15)0.7207 (4)0.0214 (12)
H11A0.87041.29390.78900.026*
C120.90791 (16)1.2173 (16)0.6620 (4)0.0266 (13)
C130.90870 (16)1.0734 (15)0.5623 (4)0.0241 (13)
C140.87108 (16)0.9157 (15)0.5212 (4)0.0219 (12)
C150.83293 (16)0.9046 (14)0.5784 (4)0.0189 (11)
H150.80700.80460.54960.023*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0204 (7)0.0272 (7)0.0257 (7)−0.0018 (6)−0.0025 (5)−0.0039 (6)
O10.026 (2)0.031 (2)0.0151 (17)−0.0024 (18)−0.0023 (15)−0.0001 (17)
O20.0211 (19)0.036 (2)0.0122 (18)0.0034 (17)−0.0014 (14)−0.0031 (16)
O30.022 (2)0.049 (3)0.034 (2)−0.014 (2)−0.0055 (17)0.006 (2)
O40.021 (2)0.070 (4)0.028 (2)−0.009 (2)0.0042 (17)0.011 (2)
O50.0199 (18)0.042 (2)0.0118 (17)−0.0017 (18)0.0023 (14)−0.0004 (17)
O1w0.027 (2)0.056 (3)0.079 (3)0.013 (2)0.012 (2)0.017 (3)
O2w0.0223 (18)0.035 (2)0.0139 (17)0.0042 (17)−0.0002 (14)−0.0012 (17)
N10.015 (2)0.024 (2)0.019 (2)0.0020 (18)−0.0001 (17)0.0006 (19)
N20.018 (2)0.026 (2)0.0121 (19)−0.0012 (19)0.0017 (17)−0.0016 (19)
C10.023 (3)0.016 (3)0.014 (2)0.002 (2)−0.001 (2)0.002 (2)
C20.027 (3)0.022 (3)0.013 (2)0.002 (2)0.005 (2)0.000 (2)
C30.022 (3)0.023 (3)0.026 (3)0.000 (2)0.009 (2)0.000 (2)
C40.017 (3)0.017 (3)0.023 (3)0.001 (2)0.000 (2)−0.003 (2)
C50.025 (3)0.020 (3)0.013 (2)0.004 (2)0.001 (2)0.000 (2)
C60.022 (3)0.018 (3)0.014 (2)0.002 (2)0.002 (2)−0.001 (2)
C70.024 (3)0.016 (3)0.011 (2)0.005 (2)0.003 (2)0.001 (2)
C90.021 (3)0.018 (3)0.015 (3)0.001 (2)−0.001 (2)0.002 (2)
C100.019 (3)0.023 (3)0.013 (2)0.003 (2)−0.003 (2)0.006 (2)
C110.022 (3)0.024 (3)0.018 (3)0.001 (2)−0.004 (2)0.001 (2)
C120.019 (3)0.036 (3)0.025 (3)−0.007 (2)−0.006 (2)0.013 (3)
C130.017 (3)0.035 (3)0.020 (3)−0.001 (2)0.000 (2)0.009 (2)
C140.024 (3)0.029 (3)0.013 (2)0.000 (2)−0.002 (2)0.007 (2)
C150.018 (3)0.022 (3)0.017 (2)−0.001 (2)−0.002 (2)0.002 (2)

Geometric parameters (Å, °)

Cl1—C41.747 (5)C1—C61.403 (6)
O1—C11.365 (6)C2—C31.371 (7)
O1—H10.8400C2—H2A0.9500
O2—C91.247 (6)C3—C41.395 (7)
O3—C121.371 (6)C3—H3A0.9500
O3—H30.8400C4—C51.376 (7)
O4—C131.361 (6)C5—C61.403 (7)
O4—H40.8400C5—H5A0.9500
O5—C141.366 (6)C6—C71.450 (7)
O5—H50.8400C7—H70.9500
O1w—H110.8347C9—C101.474 (7)
O1w—H120.8378C10—C111.384 (7)
O2w—H210.8421C10—C151.408 (7)
O2w—H220.8400C11—C121.377 (7)
N1—C71.283 (6)C11—H11A0.9500
N1—N21.386 (6)C12—C131.395 (8)
N2—C91.350 (6)C13—C141.394 (7)
N2—H20.8800C14—C151.385 (7)
C1—C21.384 (7)C15—H150.9500
C1—O1—H1109.5C1—C6—C7122.9 (4)
C12—O3—H3109.5C5—C6—C7118.3 (4)
C13—O4—H4109.5N1—C7—C6121.0 (4)
C14—O5—H5109.5N1—C7—H7119.5
H11—O1w—H12110.0C6—C7—H7119.5
H21—O2w—H22109.0O2—C9—N2122.2 (4)
C7—N1—N2115.9 (4)O2—C9—C10122.6 (4)
C9—N2—N1121.2 (4)N2—C9—C10115.1 (4)
C9—N2—H2119.4C11—C10—C15120.3 (5)
N1—N2—H2119.4C11—C10—C9119.7 (4)
O1—C1—C2118.6 (4)C15—C10—C9119.9 (4)
O1—C1—C6121.4 (4)C12—C11—C10120.0 (5)
C2—C1—C6120.0 (4)C12—C11—H11A120.0
C3—C2—C1121.2 (5)C10—C11—H11A120.0
C3—C2—H2A119.4O3—C12—C11119.0 (5)
C1—C2—H2A119.4O3—C12—C13120.5 (5)
C2—C3—C4119.0 (5)C11—C12—C13120.5 (5)
C2—C3—H3A120.5O4—C13—C14123.5 (5)
C4—C3—H3A120.5O4—C13—C12116.8 (5)
C5—C4—C3121.1 (5)C14—C13—C12119.7 (5)
C5—C4—Cl1119.4 (4)O5—C14—C15123.4 (4)
C3—C4—Cl1119.5 (4)O5—C14—C13116.2 (4)
C4—C5—C6119.9 (4)C15—C14—C13120.3 (5)
C4—C5—H5A120.0C14—C15—C10119.2 (4)
C6—C5—H5A120.0C14—C15—H15120.4
C1—C6—C5118.8 (5)C10—C15—H15120.4
C7—N1—N2—C9−166.9 (5)N2—C9—C10—C11154.5 (5)
O1—C1—C2—C3−180.0 (5)O2—C9—C10—C15148.7 (5)
C6—C1—C2—C3−1.1 (8)N2—C9—C10—C15−29.5 (7)
C1—C2—C3—C41.0 (8)C15—C10—C11—C12−0.4 (8)
C2—C3—C4—C5−0.6 (8)C9—C10—C11—C12175.6 (5)
C2—C3—C4—Cl1178.0 (4)C10—C11—C12—O3−179.3 (5)
C3—C4—C5—C60.2 (8)C10—C11—C12—C13−1.2 (8)
Cl1—C4—C5—C6−178.4 (4)O3—C12—C13—O4−0.1 (8)
O1—C1—C6—C5179.6 (5)C11—C12—C13—O4−178.2 (5)
C2—C1—C6—C50.7 (7)O3—C12—C13—C14179.2 (5)
O1—C1—C6—C71.2 (8)C11—C12—C13—C141.1 (8)
C2—C1—C6—C7−177.7 (5)O4—C13—C14—O51.3 (8)
C4—C5—C6—C1−0.3 (7)C12—C13—C14—O5−178.0 (5)
C4—C5—C6—C7178.2 (5)O4—C13—C14—C15179.9 (5)
N2—N1—C7—C6176.3 (4)C12—C13—C14—C150.6 (8)
C1—C6—C7—N1−0.1 (8)O5—C14—C15—C10176.3 (5)
C5—C6—C7—N1−178.5 (5)C13—C14—C15—C10−2.2 (8)
N1—N2—C9—O2−13.1 (8)C11—C10—C15—C142.1 (7)
N1—N2—C9—C10165.1 (4)C9—C10—C15—C14−173.9 (5)
O2—C9—C10—C11−27.4 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.841.892.631 (5)146
O3—H3···O1wi0.841.962.737 (6)153
O4—H4···O1wii0.841.802.599 (7)158
O5—H5···O2ii0.841.932.765 (5)171
O1w—H11···O30.832.282.969 (6)140
O1w—H12···O4iii0.842.072.900 (7)170
O2w—H21···O10.842.152.946 (5)157
O2w—H22···O2iv0.841.972.808 (5)172
N2—H2···O2wii0.882.032.882 (5)162

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+5/2, z+1/2; (iv) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2403).

References

  • Ali, H. M., Puvaneswary, S. & Ng, S. W. (2005). Acta Cryst. E61, o3464–o3465.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). 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. (2009). publCIF In preparation.
  • Xu, H.-M. & Liu, S.-X. (2006). Acta Cryst. E62, o3026–o3027.

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