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3,4,5-Trihydr­­oxy-N′-(2-hydr­­oxy-5-nitro­benzyl­­idene)benzohydrazide mono­hydrate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 18 March 2009; accepted 23 March 2009; online 28 March 2009)

The benzohydrazide mol­ecule of the title compound, C14H11N3O7·H2O, is planar (r.m.s. deviation = 0.068 Å). The benzohydrazide mol­ecule and the uncoordinated water mol­ecule inter­act through O—H⋯O hydrogen bonds; these together with O—H⋯N and N—H⋯O hydrogen bonds form a three-dimensional network.

Related literature

For the the parent N′-(2-hydroxy­benzyl­idene)benzohydrazide, see: Lyubchova et al. (1995[Lyubchova, A., Cossé-Barbi, A., Doucet, J. P., Robert, F., Souron, J.-P. & Quarton, M. (1995). Acta Cryst. C51, 1893-1895.]). For other N′-(2-hydr­oxy-5-nitro­benzyl­idene)benzohydrazides, see: Ali et al. (2005[Ali, H. M., Puvaneswary, S. & Ng, S. W. (2005). Acta Cryst. E61, o3464-o3465.]); Lyubchova et al. (1995[Lyubchova, A., Cossé-Barbi, A., Doucet, J. P., Robert, F., Souron, J.-P. & Quarton, M. (1995). Acta Cryst. C51, 1893-1895.]); Xu & Liu (2006[Xu, H.-M. & Liu, S.-X. (2006). Acta Cryst. E62, o3026-o3027.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11N3O7·H2O

  • Mr = 351.27

  • Triclinic, [P \overline 1]

  • a = 7.0097 (2) Å

  • b = 7.8380 (2) Å

  • c = 13.2953 (3) Å

  • α = 75.597 (1)°

  • β = 88.826 (2)°

  • γ = 81.929 (2)°

  • V = 700.42 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.14 mm−1

  • T = 123 K

  • 0.15 × 0.10 × 0.02 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 6629 measured reflections

  • 3209 independent reflections

  • 2373 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.112

  • S = 1.03

  • 3209 reflections

  • 254 parameters

  • 7 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N2 0.84 (1) 1.81 (1) 2.581 (2) 152 (2)
O5—H5⋯O6i 0.84 (1) 2.16 (2) 2.847 (2) 139 (2)
O6—H6⋯O1wii 0.84 (1) 1.81 (1) 2.630 (2) 162 (2)
O7—H7⋯O4iii 0.84 (1) 1.87 (1) 2.715 (2) 177 (2)
O1w—H11⋯O5 0.84 (1) 2.13 (1) 2.918 (2) 156 (2)
O1w—H12⋯O1iv 0.84 (1) 2.13 (1) 2.962 (2) 169 (2)
N3—H3⋯O3v 0.88 (1) 2.07 (1) 2.890 (2) 155 (2)
Symmetry codes: (i) -x+2, -y+2, -z; (ii) x+1, y, z; (iii) -x+2, -y+2, -z+1; (iv) -x+1, -y+2, -z+1; (v) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

5-Nitro-2-hydroxybenzaldehyde (0.33 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 top

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 and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88±0.01 Å and O–H 0.84±0.01 Å, respectively; their temperature factors were refined isotropically.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C14H11N3O7.H2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
3,4,5-Trihydroxy-N'-(2-hydroxy-5-nitrobenzylidene)benzohydrazide monohydrate top
Crystal data top
C14H11N3O7·H2OZ = 2
Mr = 351.27F(000) = 364
Triclinic, P1Dx = 1.666 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0097 (2) ÅCell parameters from 2084 reflections
b = 7.8380 (2) Åθ = 2.7–28.3°
c = 13.2953 (3) ŵ = 0.14 mm1
α = 75.597 (1)°T = 123 K
β = 88.826 (2)°Plate, yellow
γ = 81.929 (2)°0.15 × 0.10 × 0.02 mm
V = 700.42 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer
2373 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 27.5°, θmin = 1.6°
ω scansh = 99
6629 measured reflectionsk = 1010
3209 independent reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1907P]
where P = (Fo2 + 2Fc2)/3
3209 reflections(Δ/σ)max = 0.001
254 parametersΔρmax = 0.42 e Å3
7 restraintsΔρmin = 0.25 e Å3
Crystal data top
C14H11N3O7·H2Oγ = 81.929 (2)°
Mr = 351.27V = 700.42 (3) Å3
Triclinic, P1Z = 2
a = 7.0097 (2) ÅMo Kα radiation
b = 7.8380 (2) ŵ = 0.14 mm1
c = 13.2953 (3) ÅT = 123 K
α = 75.597 (1)°0.15 × 0.10 × 0.02 mm
β = 88.826 (2)°
Data collection top
Bruker SMART APEX
diffractometer
2373 reflections with I > 2σ(I)
6629 measured reflectionsRint = 0.019
3209 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0387 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.42 e Å3
3209 reflectionsΔρmin = 0.25 e Å3
254 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.45792 (16)0.65420 (15)0.74975 (9)0.0199 (3)
O20.28084 (18)0.28619 (17)0.85473 (9)0.0280 (3)
O30.29787 (16)0.35460 (16)0.68665 (9)0.0235 (3)
O40.75724 (17)0.84619 (16)0.53567 (9)0.0241 (3)
O50.70666 (16)1.00100 (17)0.07165 (8)0.0216 (3)
O61.05293 (16)1.11263 (16)0.08126 (8)0.0195 (3)
O71.21628 (16)1.10003 (17)0.27137 (9)0.0216 (3)
O1W0.36719 (17)1.26409 (18)0.06982 (9)0.0236 (3)
N10.21856 (19)0.35371 (18)0.76939 (10)0.0188 (3)
N20.43352 (19)0.71596 (18)0.55014 (10)0.0174 (3)
N30.50987 (19)0.77875 (19)0.45456 (10)0.0182 (3)
C10.2933 (2)0.5835 (2)0.75146 (12)0.0170 (3)
C20.2175 (2)0.5116 (2)0.84825 (12)0.0206 (3)
H20.28240.51360.90990.025*
C30.0492 (2)0.4379 (2)0.85482 (12)0.0196 (3)
H3A0.00270.38900.92060.024*
C40.0440 (2)0.4361 (2)0.76366 (12)0.0173 (3)
C50.0277 (2)0.5064 (2)0.66704 (12)0.0172 (3)
H5A0.03920.50420.60600.021*
C60.1980 (2)0.5805 (2)0.65926 (12)0.0166 (3)
C70.2744 (2)0.6509 (2)0.55666 (12)0.0179 (3)
H7A0.20750.64850.49570.021*
C80.6794 (2)0.8441 (2)0.45388 (12)0.0158 (3)
C90.7687 (2)0.9115 (2)0.35203 (11)0.0152 (3)
C100.6888 (2)0.9198 (2)0.25525 (12)0.0157 (3)
H100.56830.87980.25040.019*
C110.7882 (2)0.9876 (2)0.16644 (11)0.0160 (3)
C120.9662 (2)1.0473 (2)0.17210 (12)0.0154 (3)
C131.0437 (2)1.0389 (2)0.26925 (12)0.0159 (3)
C140.9458 (2)0.9706 (2)0.35795 (12)0.0164 (3)
H140.99980.96370.42400.020*
H10.482 (3)0.691 (3)0.6866 (9)0.043 (7)*
H50.789 (3)1.020 (3)0.0256 (16)0.060 (8)*
H61.151 (2)1.158 (3)0.0912 (18)0.045 (7)*
H71.228 (3)1.117 (3)0.3308 (10)0.045 (7)*
H110.452 (3)1.191 (3)0.0523 (19)0.047 (7)*
H120.408 (3)1.278 (3)0.1260 (12)0.055 (8)*
H30.453 (3)0.769 (2)0.3981 (10)0.022 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0212 (6)0.0250 (6)0.0149 (6)0.0097 (5)0.0003 (5)0.0041 (5)
O20.0256 (6)0.0346 (7)0.0205 (6)0.0096 (5)0.0064 (5)0.0017 (5)
O30.0212 (6)0.0307 (7)0.0219 (6)0.0077 (5)0.0003 (5)0.0102 (5)
O40.0268 (6)0.0361 (7)0.0116 (5)0.0148 (5)0.0000 (5)0.0040 (5)
O50.0172 (6)0.0399 (7)0.0094 (5)0.0089 (5)0.0009 (4)0.0067 (5)
O60.0184 (6)0.0301 (7)0.0117 (5)0.0098 (5)0.0032 (4)0.0053 (5)
O70.0186 (6)0.0368 (7)0.0134 (6)0.0132 (5)0.0016 (5)0.0087 (5)
O1W0.0215 (6)0.0334 (7)0.0169 (6)0.0077 (5)0.0004 (5)0.0060 (5)
N10.0174 (7)0.0206 (7)0.0181 (7)0.0030 (5)0.0028 (5)0.0041 (6)
N20.0194 (7)0.0200 (7)0.0123 (6)0.0046 (5)0.0033 (5)0.0023 (5)
N30.0186 (7)0.0271 (8)0.0095 (6)0.0077 (6)0.0015 (5)0.0034 (5)
C10.0184 (7)0.0166 (8)0.0163 (8)0.0028 (6)0.0003 (6)0.0045 (6)
C20.0251 (8)0.0233 (9)0.0133 (8)0.0045 (7)0.0013 (6)0.0038 (6)
C30.0241 (8)0.0213 (8)0.0124 (7)0.0042 (7)0.0032 (6)0.0016 (6)
C40.0176 (7)0.0166 (8)0.0173 (8)0.0031 (6)0.0027 (6)0.0036 (6)
C50.0185 (7)0.0192 (8)0.0135 (7)0.0019 (6)0.0007 (6)0.0036 (6)
C60.0181 (8)0.0178 (8)0.0134 (7)0.0024 (6)0.0009 (6)0.0032 (6)
C70.0202 (8)0.0215 (8)0.0124 (7)0.0043 (6)0.0001 (6)0.0044 (6)
C80.0177 (7)0.0169 (8)0.0127 (7)0.0029 (6)0.0005 (6)0.0034 (6)
C90.0174 (7)0.0170 (8)0.0110 (7)0.0024 (6)0.0022 (6)0.0034 (6)
C100.0131 (7)0.0202 (8)0.0145 (7)0.0031 (6)0.0008 (6)0.0051 (6)
C110.0166 (7)0.0207 (8)0.0112 (7)0.0014 (6)0.0002 (6)0.0056 (6)
C120.0154 (7)0.0183 (8)0.0121 (7)0.0024 (6)0.0028 (6)0.0034 (6)
C130.0143 (7)0.0196 (8)0.0147 (7)0.0045 (6)0.0004 (6)0.0048 (6)
C140.0185 (7)0.0198 (8)0.0116 (7)0.0039 (6)0.0018 (6)0.0043 (6)
Geometric parameters (Å, º) top
O1—C11.3456 (19)C1—C61.415 (2)
O1—H10.840 (10)C2—C31.377 (2)
O2—N11.2263 (17)C2—H20.9500
O3—N11.2408 (17)C3—C41.393 (2)
O4—C81.2313 (18)C3—H3A0.9500
O5—C111.3684 (18)C4—C51.380 (2)
O5—H50.835 (10)C5—C61.391 (2)
O6—C121.3567 (18)C5—H5A0.9500
O6—H60.844 (10)C6—C71.460 (2)
O7—C131.3654 (18)C7—H7A0.9500
O7—H70.842 (10)C8—C91.486 (2)
O1W—H110.837 (10)C9—C141.394 (2)
O1W—H120.843 (10)C9—C101.397 (2)
N1—C41.454 (2)C10—C111.386 (2)
N2—C71.283 (2)C10—H100.9500
N2—N31.3705 (18)C11—C121.402 (2)
N3—C81.358 (2)C12—C131.394 (2)
N3—H30.882 (9)C13—C141.380 (2)
C1—C21.397 (2)C14—H140.9500
C1—O1—H1105.4 (16)C5—C6—C1118.80 (14)
C11—O5—H5109.5 (19)C5—C6—C7119.23 (14)
C12—O6—H6111.2 (16)C1—C6—C7121.96 (14)
C13—O7—H7106.8 (16)N2—C7—C6118.88 (14)
H11—O1W—H12105 (2)N2—C7—H7A120.6
O2—N1—O3122.81 (13)C6—C7—H7A120.6
O2—N1—C4119.27 (13)O4—C8—N3120.72 (14)
O3—N1—C4117.92 (13)O4—C8—C9121.07 (14)
C7—N2—N3119.72 (13)N3—C8—C9118.21 (13)
C8—N3—N2116.36 (13)C14—C9—C10119.94 (13)
C8—N3—H3123.5 (13)C14—C9—C8114.80 (13)
N2—N3—H3120.0 (13)C10—C9—C8125.25 (14)
O1—C1—C2117.78 (14)C11—C10—C9118.85 (14)
O1—C1—C6122.00 (14)C11—C10—H10120.6
C2—C1—C6120.21 (14)C9—C10—H10120.6
C3—C2—C1120.36 (15)O5—C11—C10118.74 (13)
C3—C2—H2119.8O5—C11—C12119.86 (13)
C1—C2—H2119.8C10—C11—C12121.36 (14)
C2—C3—C4119.02 (14)O6—C12—C13123.45 (13)
C2—C3—H3A120.5O6—C12—C11117.42 (13)
C4—C3—H3A120.5C13—C12—C11119.13 (13)
C5—C4—C3121.78 (14)O7—C13—C14122.96 (14)
C5—C4—N1118.55 (14)O7—C13—C12117.31 (13)
C3—C4—N1119.64 (14)C14—C13—C12119.73 (14)
C4—C5—C6119.81 (14)C13—C14—C9120.99 (14)
C4—C5—H5A120.1C13—C14—H14119.5
C6—C5—H5A120.1C9—C14—H14119.5
C7—N2—N3—C8179.41 (15)N2—N3—C8—C9179.23 (13)
O1—C1—C2—C3179.85 (15)O4—C8—C9—C141.7 (2)
C6—C1—C2—C30.3 (2)N3—C8—C9—C14177.85 (14)
C1—C2—C3—C40.0 (3)O4—C8—C9—C10177.86 (16)
C2—C3—C4—C50.1 (3)N3—C8—C9—C102.6 (2)
C2—C3—C4—N1178.09 (15)C14—C9—C10—C110.1 (2)
O2—N1—C4—C5177.95 (14)C8—C9—C10—C11179.45 (15)
O3—N1—C4—C51.8 (2)C9—C10—C11—O5177.89 (14)
O2—N1—C4—C30.3 (2)C9—C10—C11—C120.0 (2)
O3—N1—C4—C3179.95 (14)O5—C11—C12—O61.7 (2)
C3—C4—C5—C60.4 (2)C10—C11—C12—O6179.59 (14)
N1—C4—C5—C6177.79 (14)O5—C11—C12—C13177.58 (14)
C4—C5—C6—C10.7 (2)C10—C11—C12—C130.3 (2)
C4—C5—C6—C7178.65 (14)O6—C12—C13—O70.1 (2)
O1—C1—C6—C5179.54 (14)C11—C12—C13—O7179.35 (14)
C2—C1—C6—C50.6 (2)O6—C12—C13—C14179.91 (15)
O1—C1—C6—C71.2 (2)C11—C12—C13—C140.7 (2)
C2—C1—C6—C7178.71 (15)O7—C13—C14—C9179.26 (15)
N3—N2—C7—C6178.44 (14)C12—C13—C14—C90.8 (2)
C5—C6—C7—N2178.70 (15)C10—C9—C14—C130.5 (2)
C1—C6—C7—N20.6 (2)C8—C9—C14—C13179.11 (14)
N2—N3—C8—O40.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.84 (1)1.81 (1)2.581 (2)152 (2)
O5—H5···O6i0.84 (1)2.16 (2)2.847 (2)139 (2)
O6—H6···O1wii0.84 (1)1.81 (1)2.630 (2)162 (2)
O7—H7···O4iii0.84 (1)1.87 (1)2.715 (2)177 (2)
O1w—H11···O50.84 (1)2.13 (1)2.918 (2)156 (2)
O1w—H12···O1iv0.84 (1)2.13 (1)2.962 (2)169 (2)
N3—H3···O3v0.88 (1)2.07 (1)2.890 (2)155 (2)
Symmetry codes: (i) x+2, y+2, z; (ii) x+1, y, z; (iii) x+2, y+2, z+1; (iv) x+1, y+2, z+1; (v) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC14H11N3O7·H2O
Mr351.27
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)7.0097 (2), 7.8380 (2), 13.2953 (3)
α, β, γ (°)75.597 (1), 88.826 (2), 81.929 (2)
V3)700.42 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.15 × 0.10 × 0.02
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6629, 3209, 2373
Rint0.019
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.112, 1.03
No. of reflections3209
No. of parameters254
No. of restraints7
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.42, 0.25

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.84 (1)1.81 (1)2.581 (2)152 (2)
O5—H5···O6i0.84 (1)2.16 (2)2.847 (2)139 (2)
O6—H6···O1wii0.84 (1)1.81 (1)2.630 (2)162 (2)
O7—H7···O4iii0.84 (1)1.87 (1)2.715 (2)177 (2)
O1w—H11···O50.84 (1)2.13 (1)2.918 (2)156 (2)
O1w—H12···O1iv0.84 (1)2.13 (1)2.962 (2)169 (2)
N3—H3···O3v0.88 (1)2.07 (1)2.890 (2)155 (2)
Symmetry codes: (i) x+2, y+2, z; (ii) x+1, y, z; (iii) x+2, y+2, z+1; (iv) x+1, y+2, z+1; (v) x, y+1, z+1.
 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

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