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

Abdul Alhadi, A.A.; Ali, H.M.; Ng, S.W.

doi:10.1107/S1600536809010563

organic compounds

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Volume 65| Part 4| April 2009| Page o908

doi:10.1107/S1600536809010563

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

Abeer A. Abdul Alhadi,^a Hapipah Mohd. Ali ^a and Seik Weng Ng ^a ^*

^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 ). For other N′-(2-hydroxy-5-nitrobenzylidene)benzohydrazides, see: Ali et al. (2005 ); Lyubchova et al. (1995); Xu & Liu (2006 ).

Experimental

Crystal data

C₁₄H₁₁N₃O₇·H₂O
M_r = 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)
R_int = 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
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯O1^iv	0.84 (1)	2.13 (1)	2.962 (2)	169 (2)
N3—H3⋯O3^v	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 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010563/tk2399sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010563/tk2399Isup2.hkl

checkCIF report

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.

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

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·H₂O	Z = 2
M_r = 351.27	F(000) = 364
Triclinic, P1	D_x = 1.666 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0097 (2) Å	Cell parameters from 2084 reflections
b = 7.8380 (2) Å	θ = 2.7–28.3°
c = 13.2953 (3) Å	µ = 0.14 mm⁻¹
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 tube	R_int = 0.019
Graphite monochromator	θ_max = 27.5°, θ_min = 1.6°
ω scans	h = −9→9
6629 measured reflections	k = −10→10
3209 independent reflections	l = −17→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0583P)² + 0.1907P] where P = (F_o² + 2F_c²)/3
3209 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.42 e Å⁻³
7 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₄H₁₁N₃O₇·H₂O	γ = 81.929 (2)°
M_r = 351.27	V = 700.42 (3) Å³
Triclinic, P1	Z = 2
a = 7.0097 (2) Å	Mo Kα radiation
b = 7.8380 (2) Å	µ = 0.14 mm⁻¹
c = 13.2953 (3) Å	T = 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 reflections	R_int = 0.019
3209 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	7 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.42 e Å⁻³
3209 reflections	Δρ_min = −0.25 e Å⁻³
254 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.45792 (16)	0.65420 (15)	0.74975 (9)	0.0199 (3)
O2	−0.28084 (18)	0.28619 (17)	0.85473 (9)	0.0280 (3)
O3	−0.29787 (16)	0.35460 (16)	0.68665 (9)	0.0235 (3)
O4	0.75724 (17)	0.84619 (16)	0.53567 (9)	0.0241 (3)
O5	0.70666 (16)	1.00100 (17)	0.07165 (8)	0.0216 (3)
O6	1.05293 (16)	1.11263 (16)	0.08126 (8)	0.0195 (3)
O7	1.21628 (16)	1.10003 (17)	0.27137 (9)	0.0216 (3)
O1W	0.36719 (17)	1.26409 (18)	0.06982 (9)	0.0236 (3)
N1	−0.21856 (19)	0.35371 (18)	0.76939 (10)	0.0188 (3)
N2	0.43352 (19)	0.71596 (18)	0.55014 (10)	0.0174 (3)
N3	0.50987 (19)	0.77875 (19)	0.45456 (10)	0.0182 (3)
C1	0.2933 (2)	0.5835 (2)	0.75146 (12)	0.0170 (3)
C2	0.2175 (2)	0.5116 (2)	0.84825 (12)	0.0206 (3)
H2	0.2824	0.5136	0.9099	0.025*
C3	0.0492 (2)	0.4379 (2)	0.85482 (12)	0.0196 (3)
H3A	−0.0027	0.3890	0.9206	0.024*
C4	−0.0440 (2)	0.4361 (2)	0.76366 (12)	0.0173 (3)
C5	0.0277 (2)	0.5064 (2)	0.66704 (12)	0.0172 (3)
H5A	−0.0392	0.5042	0.6060	0.021*
C6	0.1980 (2)	0.5805 (2)	0.65926 (12)	0.0166 (3)
C7	0.2744 (2)	0.6509 (2)	0.55666 (12)	0.0179 (3)
H7A	0.2075	0.6485	0.4957	0.021*
C8	0.6794 (2)	0.8441 (2)	0.45388 (12)	0.0158 (3)
C9	0.7687 (2)	0.9115 (2)	0.35203 (11)	0.0152 (3)
C10	0.6888 (2)	0.9198 (2)	0.25525 (12)	0.0157 (3)
H10	0.5683	0.8798	0.2504	0.019*
C11	0.7882 (2)	0.9876 (2)	0.16644 (11)	0.0160 (3)
C12	0.9662 (2)	1.0473 (2)	0.17210 (12)	0.0154 (3)
C13	1.0437 (2)	1.0389 (2)	0.26925 (12)	0.0159 (3)
C14	0.9458 (2)	0.9706 (2)	0.35795 (12)	0.0164 (3)
H14	0.9998	0.9637	0.4240	0.020*
H1	0.482 (3)	0.691 (3)	0.6866 (9)	0.043 (7)*
H5	0.789 (3)	1.020 (3)	0.0256 (16)	0.060 (8)*
H6	1.151 (2)	1.158 (3)	0.0912 (18)	0.045 (7)*
H7	1.228 (3)	1.117 (3)	0.3308 (10)	0.045 (7)*
H11	0.452 (3)	1.191 (3)	0.0523 (19)	0.047 (7)*
H12	0.408 (3)	1.278 (3)	0.1260 (12)	0.055 (8)*
H3	0.453 (3)	0.769 (2)	0.3981 (10)	0.022 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0212 (6)	0.0250 (6)	0.0149 (6)	−0.0097 (5)	−0.0003 (5)	−0.0041 (5)
O2	0.0256 (6)	0.0346 (7)	0.0205 (6)	−0.0096 (5)	0.0064 (5)	0.0017 (5)
O3	0.0212 (6)	0.0307 (7)	0.0219 (6)	−0.0077 (5)	0.0003 (5)	−0.0102 (5)
O4	0.0268 (6)	0.0361 (7)	0.0116 (5)	−0.0148 (5)	0.0000 (5)	−0.0040 (5)
O5	0.0172 (6)	0.0399 (7)	0.0094 (5)	−0.0089 (5)	0.0009 (4)	−0.0067 (5)
O6	0.0184 (6)	0.0301 (7)	0.0117 (5)	−0.0098 (5)	0.0032 (4)	−0.0053 (5)
O7	0.0186 (6)	0.0368 (7)	0.0134 (6)	−0.0132 (5)	0.0016 (5)	−0.0087 (5)
O1W	0.0215 (6)	0.0334 (7)	0.0169 (6)	−0.0077 (5)	0.0004 (5)	−0.0060 (5)
N1	0.0174 (7)	0.0206 (7)	0.0181 (7)	−0.0030 (5)	0.0028 (5)	−0.0041 (6)
N2	0.0194 (7)	0.0200 (7)	0.0123 (6)	−0.0046 (5)	0.0033 (5)	−0.0023 (5)
N3	0.0186 (7)	0.0271 (8)	0.0095 (6)	−0.0077 (6)	0.0015 (5)	−0.0034 (5)
C1	0.0184 (7)	0.0166 (8)	0.0163 (8)	−0.0028 (6)	0.0003 (6)	−0.0045 (6)
C2	0.0251 (8)	0.0233 (9)	0.0133 (8)	−0.0045 (7)	−0.0013 (6)	−0.0038 (6)
C3	0.0241 (8)	0.0213 (8)	0.0124 (7)	−0.0042 (7)	0.0032 (6)	−0.0016 (6)
C4	0.0176 (7)	0.0166 (8)	0.0173 (8)	−0.0031 (6)	0.0027 (6)	−0.0036 (6)
C5	0.0185 (7)	0.0192 (8)	0.0135 (7)	−0.0019 (6)	−0.0007 (6)	−0.0036 (6)
C6	0.0181 (8)	0.0178 (8)	0.0134 (7)	−0.0024 (6)	0.0009 (6)	−0.0032 (6)
C7	0.0202 (8)	0.0215 (8)	0.0124 (7)	−0.0043 (6)	−0.0001 (6)	−0.0044 (6)
C8	0.0177 (7)	0.0169 (8)	0.0127 (7)	−0.0029 (6)	0.0005 (6)	−0.0034 (6)
C9	0.0174 (7)	0.0170 (8)	0.0110 (7)	−0.0024 (6)	0.0022 (6)	−0.0034 (6)
C10	0.0131 (7)	0.0202 (8)	0.0145 (7)	−0.0031 (6)	0.0008 (6)	−0.0051 (6)
C11	0.0166 (7)	0.0207 (8)	0.0112 (7)	−0.0014 (6)	−0.0002 (6)	−0.0056 (6)
C12	0.0154 (7)	0.0183 (8)	0.0121 (7)	−0.0024 (6)	0.0028 (6)	−0.0034 (6)
C13	0.0143 (7)	0.0196 (8)	0.0147 (7)	−0.0045 (6)	0.0004 (6)	−0.0048 (6)
C14	0.0185 (7)	0.0198 (8)	0.0116 (7)	−0.0039 (6)	−0.0018 (6)	−0.0043 (6)

Geometric parameters (Å, º) top

O1—C1	1.3456 (19)	C1—C6	1.415 (2)
O1—H1	0.840 (10)	C2—C3	1.377 (2)
O2—N1	1.2263 (17)	C2—H2	0.9500
O3—N1	1.2408 (17)	C3—C4	1.393 (2)
O4—C8	1.2313 (18)	C3—H3A	0.9500
O5—C11	1.3684 (18)	C4—C5	1.380 (2)
O5—H5	0.835 (10)	C5—C6	1.391 (2)
O6—C12	1.3567 (18)	C5—H5A	0.9500
O6—H6	0.844 (10)	C6—C7	1.460 (2)
O7—C13	1.3654 (18)	C7—H7A	0.9500
O7—H7	0.842 (10)	C8—C9	1.486 (2)
O1W—H11	0.837 (10)	C9—C14	1.394 (2)
O1W—H12	0.843 (10)	C9—C10	1.397 (2)
N1—C4	1.454 (2)	C10—C11	1.386 (2)
N2—C7	1.283 (2)	C10—H10	0.9500
N2—N3	1.3705 (18)	C11—C12	1.402 (2)
N3—C8	1.358 (2)	C12—C13	1.394 (2)
N3—H3	0.882 (9)	C13—C14	1.380 (2)
C1—C2	1.397 (2)	C14—H14	0.9500

C1—O1—H1	105.4 (16)	C5—C6—C1	118.80 (14)
C11—O5—H5	109.5 (19)	C5—C6—C7	119.23 (14)
C12—O6—H6	111.2 (16)	C1—C6—C7	121.96 (14)
C13—O7—H7	106.8 (16)	N2—C7—C6	118.88 (14)
H11—O1W—H12	105 (2)	N2—C7—H7A	120.6
O2—N1—O3	122.81 (13)	C6—C7—H7A	120.6
O2—N1—C4	119.27 (13)	O4—C8—N3	120.72 (14)
O3—N1—C4	117.92 (13)	O4—C8—C9	121.07 (14)
C7—N2—N3	119.72 (13)	N3—C8—C9	118.21 (13)
C8—N3—N2	116.36 (13)	C14—C9—C10	119.94 (13)
C8—N3—H3	123.5 (13)	C14—C9—C8	114.80 (13)
N2—N3—H3	120.0 (13)	C10—C9—C8	125.25 (14)
O1—C1—C2	117.78 (14)	C11—C10—C9	118.85 (14)
O1—C1—C6	122.00 (14)	C11—C10—H10	120.6
C2—C1—C6	120.21 (14)	C9—C10—H10	120.6
C3—C2—C1	120.36 (15)	O5—C11—C10	118.74 (13)
C3—C2—H2	119.8	O5—C11—C12	119.86 (13)
C1—C2—H2	119.8	C10—C11—C12	121.36 (14)
C2—C3—C4	119.02 (14)	O6—C12—C13	123.45 (13)
C2—C3—H3A	120.5	O6—C12—C11	117.42 (13)
C4—C3—H3A	120.5	C13—C12—C11	119.13 (13)
C5—C4—C3	121.78 (14)	O7—C13—C14	122.96 (14)
C5—C4—N1	118.55 (14)	O7—C13—C12	117.31 (13)
C3—C4—N1	119.64 (14)	C14—C13—C12	119.73 (14)
C4—C5—C6	119.81 (14)	C13—C14—C9	120.99 (14)
C4—C5—H5A	120.1	C13—C14—H14	119.5
C6—C5—H5A	120.1	C9—C14—H14	119.5

C7—N2—N3—C8	−179.41 (15)	N2—N3—C8—C9	179.23 (13)
O1—C1—C2—C3	179.85 (15)	O4—C8—C9—C14	1.7 (2)
C6—C1—C2—C3	−0.3 (2)	N3—C8—C9—C14	−177.85 (14)
C1—C2—C3—C4	0.0 (3)	O4—C8—C9—C10	−177.86 (16)
C2—C3—C4—C5	−0.1 (3)	N3—C8—C9—C10	2.6 (2)
C2—C3—C4—N1	178.09 (15)	C14—C9—C10—C11	−0.1 (2)
O2—N1—C4—C5	177.95 (14)	C8—C9—C10—C11	179.45 (15)
O3—N1—C4—C5	−1.8 (2)	C9—C10—C11—O5	−177.89 (14)
O2—N1—C4—C3	−0.3 (2)	C9—C10—C11—C12	0.0 (2)
O3—N1—C4—C3	179.95 (14)	O5—C11—C12—O6	−1.7 (2)
C3—C4—C5—C6	0.4 (2)	C10—C11—C12—O6	−179.59 (14)
N1—C4—C5—C6	−177.79 (14)	O5—C11—C12—C13	177.58 (14)
C4—C5—C6—C1	−0.7 (2)	C10—C11—C12—C13	−0.3 (2)
C4—C5—C6—C7	178.65 (14)	O6—C12—C13—O7	−0.1 (2)
O1—C1—C6—C5	−179.54 (14)	C11—C12—C13—O7	−179.35 (14)
C2—C1—C6—C5	0.6 (2)	O6—C12—C13—C14	179.91 (15)
O1—C1—C6—C7	1.2 (2)	C11—C12—C13—C14	0.7 (2)
C2—C1—C6—C7	−178.71 (15)	O7—C13—C14—C9	179.26 (15)
N3—N2—C7—C6	178.44 (14)	C12—C13—C14—C9	−0.8 (2)
C5—C6—C7—N2	−178.70 (15)	C10—C9—C14—C13	0.5 (2)
C1—C6—C7—N2	0.6 (2)	C8—C9—C14—C13	−179.11 (14)
N2—N3—C8—O4	−0.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···O1^iv	0.84 (1)	2.13 (1)	2.962 (2)	169 (2)
N3—H3···O3^v	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.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₇·H₂O
M_r	351.27
Crystal system, space group	Triclinic, 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)
V (Å³)	700.42 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.15 × 0.10 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6629, 3209, 2373
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.112, 1.03
No. of reflections	3209
No. of parameters	254
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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···O1^iv	0.84 (1)	2.13 (1)	2.962 (2)	169 (2)
N3—H3···O3^v	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.

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Ali, H. M., Puvaneswary, S. & Ng, S. W. (2005). Acta Cryst. E61, o3464–o3465. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lyubchova, A., Cossé-Barbi, A., Doucet, J. P., Robert, F., Souron, J.-P. & Quarton, M. (1995). Acta Cryst. C51, 1893–1895. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Xu, H.-M. & Liu, S.-X. (2006). Acta Cryst. E62, o3026–o3027. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 4| April 2009| Page o908

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

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