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

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

doi:10.1107/S1600536809010812

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o910

doi:10.1107/S1600536809010812

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

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 23 March 2009; accepted 24 March 2009; online 28 March 2009)

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

Experimental

Crystal data

C₁₄H₁₁ClN₂O₅·2H₂O
M_r = 358.73
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.071
wR(F²) = 0.181
S = 1.07
2623 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.89	2.631 (5)	146
O3—H3⋯O1wⁱ	0.84	1.96	2.737 (6)	153
O4—H4⋯O1wⁱⁱ	0.84	1.80	2.599 (7)	158
O5—H5⋯O2ⁱⁱ	0.84	1.93	2.765 (5)	171
O1w—H11⋯O3	0.83	2.28	2.969 (6)	140
O1w—H12⋯O4ⁱⁱⁱ	0.84	2.07	2.900 (7)	170
O2w—H21⋯O1	0.84	2.15	2.946 (5)	157
O2w—H22⋯O2^iv	0.84	1.97	2.808 (5)	172
N2—H2⋯O2wⁱⁱ	0.88	2.03	2.882 (5)	162
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x, y-1, z.

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/S1600536809010812/tk2403sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010812/tk2403Isup2.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-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.

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 C₁₄H₁₁ClN₂O₅^.2H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₁₄H₁₁ClN₂O₅·2H₂O	F(000) = 744
M_r = 358.73	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1505 reflections
a = 30.5627 (12) Å	θ = 2.7–24.3°
b = 3.7539 (2) Å	µ = 0.30 mm⁻¹
c = 12.8882 (5) Å	T = 100 K
β = 90.450 (3)°	Prism, yellow
V = 1478.61 (11) Å³	0.36 × 0.04 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2623 independent reflections
Radiation source: fine-focus sealed tube	1801 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
ω scans	θ_max = 25.0°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→36
T_min = 0.899, T_max = 0.988	k = −4→4
10104 measured reflections	l = −15→14

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0537P)² + 5.5995P] where P = (F_o² + 2F_c²)/3
2623 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₄H₁₁ClN₂O₅·2H₂O	V = 1478.61 (11) Å³
M_r = 358.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 30.5627 (12) Å	µ = 0.30 mm⁻¹
b = 3.7539 (2) Å	T = 100 K
c = 12.8882 (5) Å	0.36 × 0.04 × 0.04 mm
β = 90.450 (3)°

Data collection top

Bruker SMART APEX diffractometer	2623 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1801 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.988	R_int = 0.097
10104 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.181	H-atom parameters constrained
S = 1.07	Δρ_max = 0.38 e Å⁻³
2623 reflections	Δρ_min = −0.49 e Å⁻³
221 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.53161 (4)	0.3168 (4)	0.59750 (10)	0.0244 (3)
O1	0.67086 (11)	0.6471 (10)	0.8994 (2)	0.0243 (9)
H1	0.6933	0.7236	0.8694	0.036*
O2	0.79657 (11)	0.9733 (10)	0.8420 (2)	0.0232 (9)
O3	0.94472 (12)	1.3696 (12)	0.7043 (3)	0.0349 (10)
H3	0.9663	1.3279	0.6661	0.052*
O4	0.94729 (12)	1.0933 (13)	0.5106 (3)	0.0395 (12)
H4	0.9481	0.9332	0.4651	0.059*
O5	0.87480 (11)	0.7706 (11)	0.4244 (2)	0.0245 (9)
H5	0.8498	0.7191	0.4013	0.037*
O1w	0.97110 (13)	0.8480 (13)	0.8663 (4)	0.0542 (14)
H11	0.9676	0.9037	0.8040	0.081*
H12	0.9666	1.0253	0.9042	0.081*
O2w	0.73755 (11)	0.1847 (10)	0.9961 (2)	0.0239 (8)
H21	0.7141	0.2633	0.9700	0.036*
H22	0.7554	0.1438	0.9482	0.036*
N1	0.71793 (13)	0.8677 (12)	0.7419 (3)	0.0194 (10)
N2	0.75565 (13)	0.9864 (12)	0.6939 (3)	0.0187 (9)
H2	0.7545	1.0529	0.6284	0.022*
C1	0.63896 (16)	0.5781 (13)	0.8275 (4)	0.0179 (11)
C2	0.60017 (17)	0.4266 (14)	0.8603 (4)	0.0209 (12)
H2A	0.5965	0.3740	0.9318	0.025*
C3	0.56699 (17)	0.3513 (14)	0.7916 (4)	0.0233 (12)
H3A	0.5403	0.2508	0.8151	0.028*
C4	0.57295 (16)	0.4243 (13)	0.6865 (4)	0.0189 (11)
C5	0.61125 (16)	0.5725 (13)	0.6514 (4)	0.0193 (11)
H5A	0.6148	0.6213	0.5797	0.023*
C6	0.64514 (16)	0.6516 (14)	0.7219 (4)	0.0179 (11)
C7	0.68550 (15)	0.7976 (13)	0.6815 (4)	0.0172 (11)
H7	0.6880	0.8421	0.6092	0.021*
C9	0.79416 (16)	1.0018 (14)	0.7457 (4)	0.0181 (11)
C10	0.83308 (16)	1.0434 (14)	0.6800 (4)	0.0183 (11)
C11	0.87050 (16)	1.1993 (15)	0.7207 (4)	0.0214 (12)
H11A	0.8704	1.2939	0.7890	0.026*
C12	0.90791 (16)	1.2173 (16)	0.6620 (4)	0.0266 (13)
C13	0.90870 (16)	1.0734 (15)	0.5623 (4)	0.0241 (13)
C14	0.87108 (16)	0.9157 (15)	0.5212 (4)	0.0219 (12)
C15	0.83293 (16)	0.9046 (14)	0.5784 (4)	0.0189 (11)
H15	0.8070	0.8046	0.5496	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0204 (7)	0.0272 (7)	0.0257 (7)	−0.0018 (6)	−0.0025 (5)	−0.0039 (6)
O1	0.026 (2)	0.031 (2)	0.0151 (17)	−0.0024 (18)	−0.0023 (15)	−0.0001 (17)
O2	0.0211 (19)	0.036 (2)	0.0122 (18)	0.0034 (17)	−0.0014 (14)	−0.0031 (16)
O3	0.022 (2)	0.049 (3)	0.034 (2)	−0.014 (2)	−0.0055 (17)	0.006 (2)
O4	0.021 (2)	0.070 (4)	0.028 (2)	−0.009 (2)	0.0042 (17)	0.011 (2)
O5	0.0199 (18)	0.042 (2)	0.0118 (17)	−0.0017 (18)	0.0023 (14)	−0.0004 (17)
O1w	0.027 (2)	0.056 (3)	0.079 (3)	0.013 (2)	0.012 (2)	0.017 (3)
O2w	0.0223 (18)	0.035 (2)	0.0139 (17)	0.0042 (17)	−0.0002 (14)	−0.0012 (17)
N1	0.015 (2)	0.024 (2)	0.019 (2)	0.0020 (18)	−0.0001 (17)	0.0006 (19)
N2	0.018 (2)	0.026 (2)	0.0121 (19)	−0.0012 (19)	0.0017 (17)	−0.0016 (19)
C1	0.023 (3)	0.016 (3)	0.014 (2)	0.002 (2)	−0.001 (2)	0.002 (2)
C2	0.027 (3)	0.022 (3)	0.013 (2)	0.002 (2)	0.005 (2)	0.000 (2)
C3	0.022 (3)	0.023 (3)	0.026 (3)	0.000 (2)	0.009 (2)	0.000 (2)
C4	0.017 (3)	0.017 (3)	0.023 (3)	0.001 (2)	0.000 (2)	−0.003 (2)
C5	0.025 (3)	0.020 (3)	0.013 (2)	0.004 (2)	0.001 (2)	0.000 (2)
C6	0.022 (3)	0.018 (3)	0.014 (2)	0.002 (2)	0.002 (2)	−0.001 (2)
C7	0.024 (3)	0.016 (3)	0.011 (2)	0.005 (2)	0.003 (2)	0.001 (2)
C9	0.021 (3)	0.018 (3)	0.015 (3)	0.001 (2)	−0.001 (2)	0.002 (2)
C10	0.019 (3)	0.023 (3)	0.013 (2)	0.003 (2)	−0.003 (2)	0.006 (2)
C11	0.022 (3)	0.024 (3)	0.018 (3)	0.001 (2)	−0.004 (2)	0.001 (2)
C12	0.019 (3)	0.036 (3)	0.025 (3)	−0.007 (2)	−0.006 (2)	0.013 (3)
C13	0.017 (3)	0.035 (3)	0.020 (3)	−0.001 (2)	0.000 (2)	0.009 (2)
C14	0.024 (3)	0.029 (3)	0.013 (2)	0.000 (2)	−0.002 (2)	0.007 (2)
C15	0.018 (3)	0.022 (3)	0.017 (2)	−0.001 (2)	−0.002 (2)	0.002 (2)

Geometric parameters (Å, º) top

Cl1—C4	1.747 (5)	C1—C6	1.403 (6)
O1—C1	1.365 (6)	C2—C3	1.371 (7)
O1—H1	0.8400	C2—H2A	0.9500
O2—C9	1.247 (6)	C3—C4	1.395 (7)
O3—C12	1.371 (6)	C3—H3A	0.9500
O3—H3	0.8400	C4—C5	1.376 (7)
O4—C13	1.361 (6)	C5—C6	1.403 (7)
O4—H4	0.8400	C5—H5A	0.9500
O5—C14	1.366 (6)	C6—C7	1.450 (7)
O5—H5	0.8400	C7—H7	0.9500
O1w—H11	0.8347	C9—C10	1.474 (7)
O1w—H12	0.8378	C10—C11	1.384 (7)
O2w—H21	0.8421	C10—C15	1.408 (7)
O2w—H22	0.8400	C11—C12	1.377 (7)
N1—C7	1.283 (6)	C11—H11A	0.9500
N1—N2	1.386 (6)	C12—C13	1.395 (8)
N2—C9	1.350 (6)	C13—C14	1.394 (7)
N2—H2	0.8800	C14—C15	1.385 (7)
C1—C2	1.384 (7)	C15—H15	0.9500

C1—O1—H1	109.5	C1—C6—C7	122.9 (4)
C12—O3—H3	109.5	C5—C6—C7	118.3 (4)
C13—O4—H4	109.5	N1—C7—C6	121.0 (4)
C14—O5—H5	109.5	N1—C7—H7	119.5
H11—O1w—H12	110.0	C6—C7—H7	119.5
H21—O2w—H22	109.0	O2—C9—N2	122.2 (4)
C7—N1—N2	115.9 (4)	O2—C9—C10	122.6 (4)
C9—N2—N1	121.2 (4)	N2—C9—C10	115.1 (4)
C9—N2—H2	119.4	C11—C10—C15	120.3 (5)
N1—N2—H2	119.4	C11—C10—C9	119.7 (4)
O1—C1—C2	118.6 (4)	C15—C10—C9	119.9 (4)
O1—C1—C6	121.4 (4)	C12—C11—C10	120.0 (5)
C2—C1—C6	120.0 (4)	C12—C11—H11A	120.0
C3—C2—C1	121.2 (5)	C10—C11—H11A	120.0
C3—C2—H2A	119.4	O3—C12—C11	119.0 (5)
C1—C2—H2A	119.4	O3—C12—C13	120.5 (5)
C2—C3—C4	119.0 (5)	C11—C12—C13	120.5 (5)
C2—C3—H3A	120.5	O4—C13—C14	123.5 (5)
C4—C3—H3A	120.5	O4—C13—C12	116.8 (5)
C5—C4—C3	121.1 (5)	C14—C13—C12	119.7 (5)
C5—C4—Cl1	119.4 (4)	O5—C14—C15	123.4 (4)
C3—C4—Cl1	119.5 (4)	O5—C14—C13	116.2 (4)
C4—C5—C6	119.9 (4)	C15—C14—C13	120.3 (5)
C4—C5—H5A	120.0	C14—C15—C10	119.2 (4)
C6—C5—H5A	120.0	C14—C15—H15	120.4
C1—C6—C5	118.8 (5)	C10—C15—H15	120.4

C7—N1—N2—C9	−166.9 (5)	N2—C9—C10—C11	154.5 (5)
O1—C1—C2—C3	−180.0 (5)	O2—C9—C10—C15	148.7 (5)
C6—C1—C2—C3	−1.1 (8)	N2—C9—C10—C15	−29.5 (7)
C1—C2—C3—C4	1.0 (8)	C15—C10—C11—C12	−0.4 (8)
C2—C3—C4—C5	−0.6 (8)	C9—C10—C11—C12	175.6 (5)
C2—C3—C4—Cl1	178.0 (4)	C10—C11—C12—O3	−179.3 (5)
C3—C4—C5—C6	0.2 (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—C5	179.6 (5)	C11—C12—C13—O4	−178.2 (5)
C2—C1—C6—C5	0.7 (7)	O3—C12—C13—C14	179.2 (5)
O1—C1—C6—C7	1.2 (8)	C11—C12—C13—C14	1.1 (8)
C2—C1—C6—C7	−177.7 (5)	O4—C13—C14—O5	1.3 (8)
C4—C5—C6—C1	−0.3 (7)	C12—C13—C14—O5	−178.0 (5)
C4—C5—C6—C7	178.2 (5)	O4—C13—C14—C15	179.9 (5)
N2—N1—C7—C6	176.3 (4)	C12—C13—C14—C15	0.6 (8)
C1—C6—C7—N1	−0.1 (8)	O5—C14—C15—C10	176.3 (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—C14	2.1 (7)
N1—N2—C9—C10	165.1 (4)	C9—C10—C15—C14	−173.9 (5)
O2—C9—C10—C11	−27.4 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.89	2.631 (5)	146
O3—H3···O1wⁱ	0.84	1.96	2.737 (6)	153
O4—H4···O1wⁱⁱ	0.84	1.80	2.599 (7)	158
O5—H5···O2ⁱⁱ	0.84	1.93	2.765 (5)	171
O1w—H11···O3	0.83	2.28	2.969 (6)	140
O1w—H12···O4ⁱⁱⁱ	0.84	2.07	2.900 (7)	170
O2w—H21···O1	0.84	2.15	2.946 (5)	157
O2w—H22···O2^iv	0.84	1.97	2.808 (5)	172
N2—H2···O2wⁱⁱ	0.88	2.03	2.882 (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.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O₅·2H₂O
M_r	358.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	30.5627 (12), 3.7539 (2), 12.8882 (5)
β (°)	90.450 (3)
V (Å³)	1478.61 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.36 × 0.04 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.899, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	10104, 2623, 1801
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.181, 1.07
No. of reflections	2623
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.49

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···N1	0.84	1.89	2.631 (5)	146
O3—H3···O1wⁱ	0.84	1.96	2.737 (6)	153
O4—H4···O1wⁱⁱ	0.84	1.80	2.599 (7)	158
O5—H5···O2ⁱⁱ	0.84	1.93	2.765 (5)	171
O1w—H11···O3	0.83	2.28	2.969 (6)	140
O1w—H12···O4ⁱⁱⁱ	0.84	2.07	2.900 (7)	170
O2w—H21···O1	0.84	2.15	2.946 (5)	157
O2w—H22···O2^iv	0.84	1.97	2.808 (5)	172
N2—H2···O2wⁱⁱ	0.88	2.03	2.882 (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.

Acknowledgements

We thank the University of Malaya for supporting this study.

References

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

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

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Experimental

Crystal data

Data collection

Refinement

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References

organic compounds

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