N′-[(E)-1-(3,5-Dichloro-2-hy­droxy­phen­yl)ethyl­idene]-4-meth­oxy­benzo­hydrazide monohydrate

He, C.-H.; Zhang, J.-P.; Chang, J.-G.

doi:10.1107/S1600536810038328

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2667

doi:10.1107/S1600536810038328

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N′-[(E)-1-(3,5-Dichloro-2-hydroxyphenyl)ethylidene]-4-methoxybenzohydrazide monohydrate

Chun-Hong He,^a Jian-Ping Zhang ^a and Jian-Guo Chang ^a ^*

^aDepartment of Materials Science and chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: tsucjg@163.com

(Received 21 September 2010; accepted 25 September 2010; online 30 September 2010)

The title compound, C₁₆H₁₄Cl₂N₂O₃·H₂O, displays a trans conformation with respect to the C=N double bond. The dihedral angle between the two benzene rings is 4.98 (12)°. Intramolecular O—H⋯N and O—H⋯O hydrogen bonds occur. The crystal structure is stabilized by intermolecular O—H⋯O and N—H⋯O hydrogen bonds. In addition, there are π–π interactions between the chemically distinct benzene rings of inversion-related molecules [centroid–centroid separation = 3.715 (1) Å].

Related literature

For further details of the chemistry of the title compound, see: Carcelli et al. (1995 ); Salem (1998 ). For a related stucture, see: Chang et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₄Cl₂N₂O₃·H₂O
M_r = 371.21
Triclinic, $[P \overline 1]$
a = 7.033 (5) Å
b = 7.516 (7) Å
c = 16.647 (10) Å
α = 85.105 (10)°
β = 81.386 (12)°
γ = 79.414 (10)°
V = 853.7 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 298 K
0.30 × 0.23 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.906, T_max = 0.946
4423 measured reflections
2936 independent reflections
1997 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.170
S = 1.00
2936 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4	0.86	2.15	2.926 (5)	150
O1—H1⋯O2	0.82	2.58	3.287 (5)	146
O1—H1⋯N1	0.82	1.77	2.484 (5)	145
O4—H16⋯O1ⁱ	0.85	2.09	2.887 (5)	156
O4—H15⋯O2ⁱⁱ	0.85	1.88	2.726 (5)	176
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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/S1600536810038328/pk2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810038328/pk2270Isup2.hkl

checkCIF report

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions and their biological activity (Carcelli et al., 1995; Salem, 1998; Chang et al., 2007). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound, was synthesized and its crystal structure is reported here.

The title molecule displays a trans conformation with respect to the C7=N1 double bond (Fig. 1). The dihedral angle between the two benzene rings is 4.98 (12) °. The crystal structure is stabilized by intramolecular O—H···N, O—H···O and intermolecular O—H···O, N—H···O hydrogen bonds. (Table. 1, Figs. 1 and 2). There are π - π interactions between the chemically distinct benzene rings on inversion related molecules [Cg···Cg = 3.715 (1) Å; Cg represents a ring centroid].

Related literature top

For further details of the chemistry of the title compound, see: Carcelli et al. (1995); Salem (1998). For a related stucture, see: Chang et al. (2007).

Experimental top

4-methoxybenzohydrazide (0.01 mol,1.66 g) was dissolved in anhydrous ethanol (50 ml), and 1-(3,5-dichloro-2-hydroxyphenyl)ethanone (0.01 mol, 2.05 g) was added. The reaction mixture was refluxed for 5 h with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 78%). The compound (1.0 mmol,0.35 g) was dissolved in dimethylformamide (30 ml) and kept at room temperature for 20d to obtain yellow single crystals suitable for X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30° probability level. Dashed lines show intramolecular O—H···N, O—H···O and intermolecular N—H···O hydrogen bonds.
	Fig. 2. Packing diagram of compound, Showing intermolecular O—H···O and N—H···O hydrogen bonds (dashed lines).

N'-[(E)-1-(3,5-Dichloro-2-hydroxyphenyl)ethylidene]-4- methoxybenzohydrazide monohydrate top

Crystal data top

C₁₆H₁₄Cl₂N₂O₃·H₂O	Z = 2
M_r = 371.21	F(000) = 384
Triclinic, P1	D_x = 1.444 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.033 (5) Å	Cell parameters from 1429 reflections
b = 7.516 (7) Å	θ = 3.0–25.5°
c = 16.647 (10) Å	µ = 0.40 mm⁻¹
α = 85.105 (10)°	T = 298 K
β = 81.386 (12)°	Plate, yellow
γ = 79.414 (10)°	0.30 × 0.23 × 0.16 mm
V = 853.7 (11) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	2936 independent reflections
Radiation source: fine-focus sealed tube	1997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
T_min = 0.906, T_max = 0.946	k = −6→8
4423 measured reflections	l = −19→19

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0727P)² + 0.8688P] where P = (F_o² + 2F_c²)/3
2936 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₄Cl₂N₂O₃·H₂O	γ = 79.414 (10)°
M_r = 371.21	V = 853.7 (11) Å³
Triclinic, P1	Z = 2
a = 7.033 (5) Å	Mo Kα radiation
b = 7.516 (7) Å	µ = 0.40 mm⁻¹
c = 16.647 (10) Å	T = 298 K
α = 85.105 (10)°	0.30 × 0.23 × 0.16 mm
β = 81.386 (12)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2936 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1997 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.946	R_int = 0.025
4423 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.00	Δρ_max = 0.56 e Å⁻³
2936 reflections	Δρ_min = −0.32 e Å⁻³
220 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	1.0655 (2)	−0.37144 (18)	0.19059 (9)	0.0675 (5)
Cl2	0.8926 (3)	0.3075 (2)	0.05875 (8)	0.0774 (6)
O1	0.9149 (5)	−0.2090 (4)	0.34325 (19)	0.0462 (8)
H1	0.8675	−0.1599	0.3856	0.069*
O2	0.7613 (6)	−0.2102 (4)	0.5397 (2)	0.0611 (10)
O3	0.5111 (6)	0.0452 (6)	0.8985 (2)	0.0714 (12)
O4	0.7853 (6)	0.4252 (4)	0.5716 (3)	0.0710 (12)
N1	0.7805 (5)	0.0497 (5)	0.4303 (2)	0.0367 (9)
N2	0.7259 (5)	0.0879 (5)	0.5112 (2)	0.0392 (9)
H2	0.6983	0.1973	0.5264	0.047*
C1	0.8427 (6)	0.1022 (6)	0.2902 (3)	0.0360 (9)
C2	0.9122 (6)	−0.0844 (6)	0.2809 (3)	0.0374 (10)
C3	0.9789 (7)	−0.1428 (6)	0.2023 (3)	0.0442 (11)
C4	0.9757 (7)	−0.0251 (7)	0.1341 (3)	0.0488 (11)
H4	1.0221	−0.0668	0.0826	0.059*
C5	0.9020 (7)	0.1566 (7)	0.1441 (3)	0.0448 (11)
C6	0.8384 (7)	0.2200 (6)	0.2203 (3)	0.0419 (10)
H6	0.7918	0.3432	0.2255	0.050*
C7	0.7781 (6)	0.1720 (6)	0.3720 (3)	0.0357 (9)
C8	0.7186 (6)	−0.0562 (6)	0.5645 (3)	0.0387 (10)
C9	0.6577 (6)	−0.0211 (6)	0.6511 (3)	0.0387 (10)
C10	0.5662 (7)	0.1480 (7)	0.6775 (3)	0.0452 (11)
H10	0.5393	0.2442	0.6396	0.054*
C11	0.5141 (7)	0.1750 (7)	0.7606 (3)	0.0508 (12)
H11	0.4542	0.2887	0.7780	0.061*
C12	0.5526 (7)	0.0310 (7)	0.8165 (3)	0.0483 (11)
C13	0.6383 (7)	−0.1378 (7)	0.7914 (3)	0.0517 (12)
H13	0.6614	−0.2346	0.8294	0.062*
C14	0.6904 (7)	−0.1634 (7)	0.7088 (3)	0.0457 (11)
H14	0.7484	−0.2780	0.6919	0.055*
C15	0.4310 (10)	0.2206 (10)	0.9292 (4)	0.0819 (19)
H15A	0.5202	0.3029	0.9109	0.123*
H15B	0.4107	0.2103	0.9876	0.123*
H15C	0.3086	0.2657	0.9095	0.123*
C16	0.7148 (6)	0.3729 (4)	0.3805 (3)	0.0605 (15)
H16A	0.6850	0.3969	0.4371	0.091*
H16B	0.6008	0.4148	0.3542	0.091*
H16C	0.8183	0.4351	0.3555	0.091*
H15	0.7839	0.5382	0.5611	0.14 (3)*
H16	0.8905	0.3884	0.5919	0.09 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0958 (12)	0.0380 (7)	0.0647 (9)	−0.0048 (7)	−0.0002 (8)	−0.0142 (6)
Cl2	0.1369 (15)	0.0568 (9)	0.0331 (7)	−0.0125 (9)	−0.0067 (8)	0.0091 (6)
O1	0.067 (2)	0.0312 (17)	0.0383 (18)	−0.0054 (15)	−0.0049 (16)	0.0012 (14)
O2	0.104 (3)	0.0296 (18)	0.046 (2)	−0.0090 (18)	−0.0052 (19)	0.0065 (15)
O3	0.089 (3)	0.084 (3)	0.034 (2)	−0.001 (2)	−0.0038 (19)	0.0013 (19)
O4	0.090 (3)	0.037 (2)	0.096 (3)	−0.0169 (19)	−0.044 (3)	0.007 (2)
N1	0.050 (2)	0.031 (2)	0.0279 (19)	−0.0080 (16)	−0.0040 (16)	0.0009 (15)
N2	0.053 (2)	0.0283 (19)	0.035 (2)	−0.0060 (16)	−0.0037 (17)	−0.0006 (16)
C1	0.038 (2)	0.039 (2)	0.032 (2)	−0.0095 (18)	−0.0057 (17)	−0.0004 (17)
C2	0.041 (2)	0.033 (2)	0.038 (2)	−0.0108 (18)	−0.0052 (18)	0.0006 (18)
C3	0.048 (2)	0.041 (2)	0.045 (2)	−0.0085 (19)	−0.005 (2)	−0.007 (2)
C4	0.057 (3)	0.049 (3)	0.040 (2)	−0.013 (2)	−0.003 (2)	−0.006 (2)
C5	0.058 (3)	0.043 (2)	0.034 (2)	−0.013 (2)	−0.007 (2)	0.0028 (19)
C6	0.048 (2)	0.038 (2)	0.038 (2)	−0.0076 (19)	−0.0049 (19)	0.0003 (19)
C7	0.043 (2)	0.031 (2)	0.033 (2)	−0.0059 (17)	−0.0058 (18)	0.0025 (17)
C8	0.047 (2)	0.029 (2)	0.039 (2)	−0.0067 (18)	−0.0073 (19)	0.0035 (18)
C9	0.040 (2)	0.040 (2)	0.037 (2)	−0.0101 (18)	−0.0062 (18)	0.0037 (18)
C10	0.051 (3)	0.043 (2)	0.039 (2)	−0.005 (2)	−0.005 (2)	0.002 (2)
C11	0.057 (3)	0.047 (3)	0.046 (3)	−0.006 (2)	−0.002 (2)	−0.002 (2)
C12	0.048 (3)	0.059 (3)	0.037 (2)	−0.008 (2)	−0.005 (2)	0.001 (2)
C13	0.051 (3)	0.058 (3)	0.043 (2)	−0.006 (2)	−0.008 (2)	0.011 (2)
C14	0.050 (3)	0.044 (2)	0.041 (2)	−0.006 (2)	−0.005 (2)	0.006 (2)
C15	0.100 (5)	0.092 (5)	0.048 (3)	−0.004 (4)	0.003 (3)	−0.018 (3)
C16	0.098 (4)	0.035 (3)	0.041 (3)	−0.001 (3)	−0.001 (3)	−0.001 (2)

Geometric parameters (Å, º) top

Cl1—C3	1.731 (5)	C5—C6	1.376 (7)
Cl2—C5	1.742 (5)	C6—H6	0.9300
O1—C2	1.338 (5)	C7—C16	1.506 (5)
O1—H1	0.8200	C8—C9	1.474 (6)
O2—C8	1.231 (5)	C9—C14	1.385 (6)
O3—C12	1.362 (6)	C9—C10	1.391 (6)
O3—C15	1.440 (7)	C10—C11	1.399 (7)
O4—H15	0.8511	C10—H10	0.9300
O4—H16	0.8496	C11—C12	1.381 (7)
N1—C7	1.279 (5)	C11—H11	0.9300
N1—N2	1.383 (5)	C12—C13	1.372 (7)
N2—C8	1.344 (5)	C13—C14	1.389 (7)
N2—H2	0.8600	C13—H13	0.9300
C1—C6	1.401 (6)	C14—H14	0.9300
C1—C2	1.412 (6)	C15—H15A	0.9600
C1—C7	1.477 (6)	C15—H15B	0.9600
C2—C3	1.401 (6)	C15—H15C	0.9600
C3—C4	1.378 (7)	C16—H16A	0.9600
C4—C5	1.383 (7)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600

C2—O1—H1	109.5	C14—C9—C10	118.5 (4)
C12—O3—C15	118.7 (5)	C14—C9—C8	118.6 (4)
H15—O4—H16	104.1	C10—C9—C8	122.9 (4)
C7—N1—N2	123.2 (4)	C9—C10—C11	120.7 (5)
C8—N2—N1	115.9 (4)	C9—C10—H10	119.7
C8—N2—H2	122.0	C11—C10—H10	119.7
N1—N2—H2	122.0	C12—C11—C10	119.3 (5)
C6—C1—C2	118.5 (4)	C12—C11—H11	120.4
C6—C1—C7	120.8 (4)	C10—C11—H11	120.4
C2—C1—C7	120.7 (4)	O3—C12—C13	115.8 (5)
O1—C2—C3	118.2 (4)	O3—C12—C11	123.4 (5)
O1—C2—C1	123.3 (4)	C13—C12—C11	120.8 (5)
C3—C2—C1	118.5 (4)	C12—C13—C14	119.6 (5)
C4—C3—C2	122.3 (4)	C12—C13—H13	120.2
C4—C3—Cl1	119.1 (4)	C14—C13—H13	120.2
C2—C3—Cl1	118.6 (4)	C9—C14—C13	121.2 (5)
C3—C4—C5	118.5 (4)	C9—C14—H14	119.4
C3—C4—H4	120.8	C13—C14—H14	119.4
C5—C4—H4	120.8	O3—C15—H15A	109.5
C6—C5—C4	121.1 (4)	O3—C15—H15B	109.5
C6—C5—Cl2	119.6 (4)	H15A—C15—H15B	109.5
C4—C5—Cl2	119.3 (4)	O3—C15—H15C	109.5
C5—C6—C1	121.1 (4)	H15A—C15—H15C	109.5
C5—C6—H6	119.5	H15B—C15—H15C	109.5
C1—C6—H6	119.5	C7—C16—H16A	109.5
N1—C7—C1	114.5 (4)	C7—C16—H16B	109.5
N1—C7—C16	125.9 (4)	H16A—C16—H16B	109.5
C1—C7—C16	119.6 (4)	C7—C16—H16C	109.5
O2—C8—N2	119.6 (4)	H16A—C16—H16C	109.5
O2—C8—C9	122.8 (4)	H16B—C16—H16C	109.5
N2—C8—C9	117.6 (4)

C7—N1—N2—C8	173.8 (4)	C6—C1—C7—C16	−2.6 (6)
C6—C1—C2—O1	−177.2 (4)	C2—C1—C7—C16	176.7 (4)
C7—C1—C2—O1	3.5 (6)	N1—N2—C8—O2	0.7 (6)
C6—C1—C2—C3	1.7 (6)	N1—N2—C8—C9	−179.0 (4)
C7—C1—C2—C3	−177.5 (4)	O2—C8—C9—C14	14.7 (7)
O1—C2—C3—C4	177.9 (4)	N2—C8—C9—C14	−165.6 (4)
C1—C2—C3—C4	−1.1 (7)	O2—C8—C9—C10	−164.4 (5)
O1—C2—C3—Cl1	−1.4 (6)	N2—C8—C9—C10	15.3 (6)
C1—C2—C3—Cl1	179.7 (3)	C14—C9—C10—C11	2.0 (7)
C2—C3—C4—C5	−0.7 (7)	C8—C9—C10—C11	−178.9 (4)
Cl1—C3—C4—C5	178.5 (4)	C9—C10—C11—C12	−0.7 (7)
C3—C4—C5—C6	1.9 (7)	C15—O3—C12—C13	176.6 (5)
C3—C4—C5—Cl2	−178.9 (4)	C15—O3—C12—C11	−2.9 (8)
C4—C5—C6—C1	−1.3 (7)	C10—C11—C12—O3	178.5 (5)
Cl2—C5—C6—C1	179.6 (4)	C10—C11—C12—C13	−1.0 (8)
C2—C1—C6—C5	−0.6 (7)	O3—C12—C13—C14	−178.2 (4)
C7—C1—C6—C5	178.7 (4)	C11—C12—C13—C14	1.3 (8)
N2—N1—C7—C1	179.8 (4)	C10—C9—C14—C13	−1.7 (7)
N2—N1—C7—C16	−0.8 (7)	C8—C9—C14—C13	179.2 (4)
C6—C1—C7—N1	176.9 (4)	C12—C13—C14—C9	0.1 (7)
C2—C1—C7—N1	−3.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.86	2.15	2.926 (5)	150
O1—H1···O2	0.82	2.58	3.287 (5)	146
O1—H1···N1	0.82	1.77	2.484 (5)	145
O4—H16···O1ⁱ	0.85	2.09	2.887 (5)	156
O4—H15···O2ⁱⁱ	0.85	1.88	2.726 (5)	176

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄Cl₂N₂O₃·H₂O
M_r	371.21
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.033 (5), 7.516 (7), 16.647 (10)
α, β, γ (°)	85.105 (10), 81.386 (12), 79.414 (10)
V (Å³)	853.7 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.30 × 0.23 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.906, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	4423, 2936, 1997
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.170, 1.00
No. of reflections	2936
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.32

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
N2—H2···O4	0.86	2.15	2.926 (5)	150.1
O1—H1···O2	0.82	2.58	3.287 (5)	145.5
O1—H1···N1	0.82	1.77	2.484 (5)	145.1
O4—H16···O1ⁱ	0.85	2.09	2.887 (5)	155.9
O4—H15···O2ⁱⁱ	0.85	1.88	2.726 (5)	175.9

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

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (No. Y05–2–09)

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43–62. CrossRef CAS PubMed Web of Science Google Scholar
Chang, J.-G. & Ji, C.-Y. (2007). Acta Cryst. E63, o3212. Web of Science CSD CrossRef IUCr Journals Google Scholar
Salem, A. A. (1998). Microchem. J. 60, 51–66. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page o2667

doi:10.1107/S1600536810038328

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

N′-[(E)-1-(3,5-Di­chloro-2-hy­dr­oxy­phen­yl)ethyl­­idene]-4-meth­­oxy­benzo­hydrazide monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[(E)-1-(3,5-Dichloro-2-hydroxyphenyl)ethylidene]-4-methoxybenzohydrazide monohydrate