(E)-N′-(5-Chloro-2-hydroxy­benzyl­idene)-3,5-dihydroxy­benzohydrazide mono­hydrate

Deng, S.; Han, L.; Huang, S.; Zhang, H.; Diao, Y.; Liu, K.

doi:10.1107/S1600536809007788

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o721

doi:10.1107/S1600536809007788

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(E)-N′-(5-Chloro-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate

Sa Deng,^a Ling Han,^b Shan-shan Huang,^a Hou-li Zhang,^a Yun-peng Diao ^a ^* and Ke-xin Liu ^a ^*

^aCollege of Pharmacy, Dalian Medical University, Liaoning 116044, People's Republic of China, and ^bLiao Ning Benxi Third Pharmaceuticals Co Ltd, Liaoning 117004, People's Republic of China
^*Correspondence e-mail: dldiaoyp@126.com, kexinliu@dlmedu.edu.cn

(Received 1 March 2009; accepted 3 March 2009; online 11 March 2009)

In the title compound, C₁₄H₁₁ClN₂O₄·H₂O, the dihedral angle between the two benzene rings is 8.5 (2)° and an intramolecular O—H⋯N hydrogen bond is observed in the Schiff base molecule. In the crystal structure, the water molecule accepts an N—H⋯O hydrogen bond and makes O—H⋯O hydrogen bonds to two further Schiff base molecules. Further intermolecular O—H⋯O hydrogen bonds lead to the formation of layers parallel to the bc plane.

Related literature

For background to the synthesis of Schiff base compounds, see: Herrick et al. (2008 ); Suresh et al. (2007 ). For the biological activity of Schiff base compounds, see: Bhandari et al. (2008 ); Sinha et al. (2008 ). For a related structure, see: Jiang et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₄·H₂O
M_r = 324.71
Monoclinic, P 2₁ /c
a = 14.106 (3) Å
b = 8.0090 (16) Å
c = 13.127 (3) Å
β = 108.26 (3)°
V = 1408.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.943, T_max = 0.948
6975 measured reflections
2496 independent reflections
1437 reflections with I > 2σ(I)
R_int = 0.084

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.142
S = 1.04
2496 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.98	2.685 (4)	144
O1—H1⋯O5	0.82	2.47	2.952 (4)	119
O3—H3⋯O1ⁱ	0.82	2.10	2.916 (4)	173
O4—H4⋯O2ⁱⁱ	0.82	1.99	2.762 (4)	158
N2—H2⋯O5ⁱⁱ	0.86	2.09	2.931 (4)	164
O5—H5A⋯O2	0.85	1.91	2.760 (4)	174
O5—H5B⋯O4ⁱⁱⁱ	0.85	2.11	2.902 (4)	156
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+2, -y+1, -z+2.

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007788/hb2921sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007788/hb2921Isup2.hkl

checkCIF report

Comment top

Schiff base compounds can be easily synthesized from the reaction of aldehydes with primary amines (Herrick et al., 2008; Suresh et al., 2007). These compounds show interesting biological activities, especially antimicrobial activities (Bhandari et al., 2008; Sinha et al., 2008). In this paper, the crystal structure of the title compound, (I), containing a new Schiff base compound derived from the condensation reaction of 5-chlorosalicylaldehyde with 3,5-dihydroxybenzoic acid hydrazide is reported.

The Schiff base molecule of (I) displays a trans configuration with respect to the C=N and C—N bonds (Fig. 1). All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable to those in the related compound 3,5-dihydroxy-N'-(2-hydroxybenzylidene) benzohydrazide monohydrate (Jiang et al., 2008). The Schiff base molecule is nearly planar, the dihedral angle between the two benzene rings is 8.5 (2)°. An intramolecular O—H···N hydrogen bond is observed. In the crystal structure the water molecule links three symmetry related molecules through O—H···O and O—H···N hydrogen bonds (Table 1). Together with two further intermolecular O—H···O hydrogen bonds, layers parallel to the bc plane are formed (Fig. 2).

Related literature top

For background to the synthesis of Schiff base compounds, see: Herrick et al. (2008); Suresh et al. ( 2007). For the biological activity of Schiff base compounds, see: Bhandari et al. (2008); Sinha et al. (2008). For a related structure, see: Jiang et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

5-Chlorosalicylaldehyde (0.1 mmol, 15.6 mg) and 3,5-dihydroxybenzoic acid hydrazide (0.1 mmol, 16.8 mg) were dissolved in a 95% ethanol solution (10 ml). The mixture was stirred at room temperature to give a clear solution. Light yellow blocks of (I) were formed by gradual evaporation of the solvent over a period of nine days at room temperature.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. The dashed lines indicate hydrogen bonds.
	Fig. 2. The molecular packing of (I). The donor···acceptor contacts for the intermolecular hydrogen bonds are shown as dashed lines. H atoms are omitted for clarity.

(E)-N'-(5-Chloro-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate top

Crystal data top

C₁₄H₁₁ClN₂O₄·H₂O	F(000) = 672
M_r = 324.71	D_x = 1.531 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 575 reflections
a = 14.106 (3) Å	θ = 3.1–20.4°
b = 8.0090 (16) Å	µ = 0.30 mm⁻¹
c = 13.127 (3) Å	T = 298 K
β = 108.26 (3)°	Block, light yellow
V = 1408.3 (6) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	2496 independent reflections
Radiation source: fine-focus sealed tube	1437 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −16→13
T_min = 0.943, T_max = 0.948	k = −9→7
6975 measured reflections	l = −15→15

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0453P)² + 1.0153P] where P = (F_o² + 2F_c²)/3
2496 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₄H₁₁ClN₂O₄·H₂O	V = 1408.3 (6) Å³
M_r = 324.71	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.106 (3) Å	µ = 0.30 mm⁻¹
b = 8.0090 (16) Å	T = 298 K
c = 13.127 (3) Å	0.20 × 0.20 × 0.18 mm
β = 108.26 (3)°

Data collection top

Siemens SMART CCD diffractometer	2496 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	1437 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.948	R_int = 0.084
6975 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.04	Δρ_max = 0.28 e Å⁻³
2496 reflections	Δρ_min = −0.30 e Å⁻³
202 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
Cl1	0.45135 (9)	1.22680 (17)	0.91318 (10)	0.0558 (4)
N1	0.8522 (2)	0.8948 (4)	0.8966 (3)	0.0295 (8)
N2	0.9299 (2)	0.8091 (4)	0.9689 (2)	0.0291 (8)
H2	0.9246	0.7758	1.0291	0.035*
O1	0.7409 (2)	1.0093 (4)	0.7040 (2)	0.0439 (8)
H1	0.7853	0.9523	0.7442	0.066*
O2	1.02312 (19)	0.8242 (4)	0.8572 (2)	0.0380 (8)
O3	1.3085 (2)	0.4281 (4)	1.0233 (2)	0.0491 (9)
H3	1.2983	0.4456	0.9592	0.074*
O4	1.1915 (2)	0.5757 (4)	1.3090 (2)	0.0400 (8)
H4	1.1481	0.6308	1.3229	0.060*
O5	0.8783 (2)	0.7575 (4)	0.6646 (2)	0.0434 (8)
H5A	0.9196	0.7761	0.7263	0.065*
H5B	0.8435	0.6765	0.6750	0.065*
C1	0.6935 (3)	1.0274 (5)	0.8653 (3)	0.0274 (9)
C2	0.6769 (3)	1.0606 (5)	0.7568 (3)	0.0309 (10)
C3	0.5923 (3)	1.1451 (6)	0.6983 (3)	0.0426 (12)
H3A	0.5819	1.1666	0.6260	0.051*
C4	0.5231 (3)	1.1979 (6)	0.7450 (4)	0.0437 (12)
H4A	0.4662	1.2550	0.7050	0.052*
C5	0.5392 (3)	1.1652 (6)	0.8520 (3)	0.0364 (11)
C6	0.6229 (3)	1.0829 (5)	0.9126 (3)	0.0354 (11)
H6	0.6330	1.0638	0.9851	0.042*
C7	0.7800 (3)	0.9389 (5)	0.9314 (3)	0.0298 (10)
H7	0.7838	0.9127	1.0016	0.036*
C8	1.0139 (3)	0.7786 (5)	0.9438 (3)	0.0254 (9)
C9	1.0938 (3)	0.6850 (5)	1.0242 (3)	0.0252 (9)
C10	1.1629 (3)	0.6018 (5)	0.9869 (3)	0.0291 (10)
H10	1.1574	0.6065	0.9145	0.035*
C11	1.2398 (3)	0.5122 (5)	1.0569 (3)	0.0304 (10)
C12	1.2492 (3)	0.5052 (5)	1.1645 (3)	0.0334 (10)
H12	1.3011	0.4455	1.2117	0.040*
C13	1.1801 (3)	0.5882 (5)	1.2015 (3)	0.0285 (10)
C14	1.1025 (3)	0.6788 (5)	1.1327 (3)	0.0297 (10)
H14	1.0570	0.7345	1.1587	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0391 (7)	0.0748 (10)	0.0587 (8)	0.0186 (7)	0.0226 (6)	−0.0009 (7)
N1	0.0256 (18)	0.032 (2)	0.0297 (19)	0.0018 (16)	0.0075 (15)	0.0043 (16)
N2	0.0262 (18)	0.039 (2)	0.0238 (17)	0.0072 (16)	0.0095 (15)	0.0089 (16)
O1	0.0415 (18)	0.061 (2)	0.0333 (17)	0.0121 (17)	0.0175 (15)	0.0069 (16)
O2	0.0337 (17)	0.057 (2)	0.0252 (15)	0.0057 (15)	0.0122 (13)	0.0097 (15)
O3	0.0467 (19)	0.069 (2)	0.0379 (18)	0.0283 (18)	0.0223 (16)	0.0028 (17)
O4	0.0422 (19)	0.053 (2)	0.0282 (16)	0.0143 (16)	0.0160 (14)	0.0059 (14)
O5	0.0438 (18)	0.058 (2)	0.0298 (16)	−0.0058 (17)	0.0131 (14)	−0.0021 (15)
C1	0.022 (2)	0.031 (3)	0.026 (2)	0.0015 (19)	0.0036 (17)	0.0020 (19)
C2	0.029 (2)	0.037 (3)	0.029 (2)	0.000 (2)	0.0129 (19)	0.000 (2)
C3	0.041 (3)	0.057 (3)	0.027 (2)	0.010 (2)	0.006 (2)	0.009 (2)
C4	0.034 (3)	0.050 (3)	0.042 (3)	0.012 (2)	0.004 (2)	0.009 (2)
C5	0.026 (2)	0.044 (3)	0.041 (3)	0.008 (2)	0.014 (2)	−0.002 (2)
C6	0.035 (2)	0.043 (3)	0.031 (2)	0.000 (2)	0.015 (2)	−0.001 (2)
C7	0.028 (2)	0.036 (3)	0.028 (2)	−0.003 (2)	0.0116 (18)	0.0002 (19)
C8	0.025 (2)	0.028 (2)	0.025 (2)	−0.0002 (19)	0.0087 (17)	0.0024 (18)
C9	0.024 (2)	0.029 (2)	0.025 (2)	−0.0001 (18)	0.0104 (17)	−0.0021 (18)
C10	0.031 (2)	0.034 (3)	0.025 (2)	0.002 (2)	0.0119 (18)	−0.0024 (19)
C11	0.029 (2)	0.035 (3)	0.028 (2)	0.005 (2)	0.0111 (19)	−0.002 (2)
C12	0.032 (2)	0.039 (3)	0.029 (2)	0.008 (2)	0.0097 (19)	0.003 (2)
C13	0.028 (2)	0.032 (3)	0.026 (2)	−0.001 (2)	0.0088 (18)	0.0033 (19)
C14	0.027 (2)	0.037 (3)	0.028 (2)	0.003 (2)	0.0145 (19)	−0.001 (2)

Geometric parameters (Å, º) top

Cl1—C5	1.746 (4)	C3—C4	1.372 (6)
N1—C7	1.290 (4)	C3—H3A	0.9300
N1—N2	1.386 (4)	C4—C5	1.376 (6)
N2—C8	1.348 (4)	C4—H4A	0.9300
N2—H2	0.8600	C5—C6	1.368 (6)
O1—C2	1.364 (4)	C6—H6	0.9300
O1—H1	0.8200	C7—H7	0.9300
O2—C8	1.238 (4)	C8—C9	1.484 (5)
O3—C11	1.362 (4)	C9—C10	1.391 (5)
O3—H3	0.8200	C9—C14	1.392 (5)
O4—C13	1.373 (4)	C10—C11	1.382 (5)
O4—H4	0.8200	C10—H10	0.9300
O5—H5A	0.8500	C11—C12	1.378 (5)
O5—H5B	0.8500	C12—C13	1.387 (5)
C1—C2	1.395 (5)	C12—H12	0.9300
C1—C6	1.401 (5)	C13—C14	1.386 (5)
C1—C7	1.442 (5)	C14—H14	0.9300
C2—C3	1.377 (6)

C7—N1—N2	115.8 (3)	C1—C6—H6	120.0
C8—N2—N1	119.3 (3)	N1—C7—C1	122.3 (4)
C8—N2—H2	120.4	N1—C7—H7	118.8
N1—N2—H2	120.4	C1—C7—H7	118.8
C2—O1—H1	109.5	O2—C8—N2	121.6 (3)
C11—O3—H3	109.5	O2—C8—C9	121.8 (3)
C13—O4—H4	109.5	N2—C8—C9	116.6 (3)
H5A—O5—H5B	103.8	C10—C9—C14	119.7 (4)
C2—C1—C6	118.5 (4)	C10—C9—C8	116.8 (3)
C2—C1—C7	123.3 (4)	C14—C9—C8	123.4 (3)
C6—C1—C7	118.3 (4)	C11—C10—C9	120.4 (4)
O1—C2—C3	117.5 (4)	C11—C10—H10	119.8
O1—C2—C1	122.4 (4)	C9—C10—H10	119.8
C3—C2—C1	120.1 (4)	O3—C11—C12	117.6 (4)
C4—C3—C2	121.1 (4)	O3—C11—C10	122.1 (3)
C4—C3—H3A	119.5	C12—C11—C10	120.3 (4)
C2—C3—H3A	119.5	C11—C12—C13	119.2 (4)
C3—C4—C5	119.0 (4)	C11—C12—H12	120.4
C3—C4—H4A	120.5	C13—C12—H12	120.4
C5—C4—H4A	120.5	O4—C13—C14	121.5 (3)
C6—C5—C4	121.4 (4)	O4—C13—C12	117.2 (4)
C6—C5—Cl1	118.5 (3)	C14—C13—C12	121.4 (4)
C4—C5—Cl1	120.1 (3)	C13—C14—C9	119.0 (4)
C5—C6—C1	119.9 (4)	C13—C14—H14	120.5
C5—C6—H6	120.0	C9—C14—H14	120.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.98	2.685 (4)	144
O1—H1···O5	0.82	2.47	2.952 (4)	119
O3—H3···O1ⁱ	0.82	2.10	2.916 (4)	173
O4—H4···O2ⁱⁱ	0.82	1.99	2.762 (4)	158
N2—H2···O5ⁱⁱ	0.86	2.09	2.931 (4)	164
O5—H5A···O2	0.85	1.91	2.760 (4)	174
O5—H5B···O4ⁱⁱⁱ	0.85	2.11	2.902 (4)	156

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O₄·H₂O
M_r	324.71
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.106 (3), 8.0090 (16), 13.127 (3)
β (°)	108.26 (3)
V (Å³)	1408.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.943, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	6975, 2496, 1437
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.142, 1.04
No. of reflections	2496
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.98	2.685 (4)	144
O1—H1···O5	0.82	2.47	2.952 (4)	119
O3—H3···O1ⁱ	0.82	2.10	2.916 (4)	173
O4—H4···O2ⁱⁱ	0.82	1.99	2.762 (4)	158
N2—H2···O5ⁱⁱ	0.86	2.09	2.931 (4)	164
O5—H5A···O2	0.85	1.91	2.760 (4)	174
O5—H5B···O4ⁱⁱⁱ	0.85	2.11	2.902 (4)	156

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

Acknowledgements

This work was supported by a Project of the Dalian Science and Technology Bureau (grant No. 2008E11SF168).

References

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Volume 65| Part 4| April 2009| Page o721

doi:10.1107/S1600536809007788

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

(E)-N′-(5-Chloro-2-hy­droxy­benzyl­­idene)-3,5-di­hydroxy­benzohydrazide mono­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-(5-Chloro-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide monohydrate