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

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

doi:10.1107/S1600536810037293

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2620

doi:10.1107/S1600536810037293

Open

access

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

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

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

(Received 9 August 2010; accepted 17 September 2010; online 25 September 2010)

The title compound, C₁₇H₁₆Cl₂N₂O₃·H₂O, displays a trans conformation with respect to the C=N double bond. The dihedral angle between the two benzene rings is 30.77 (5)° and there is one intramolecular N—H⋯O hydrogen bond. In the crystal, molecules are linked by hydrogen bonding to the water molecules of crystallization, which acts as both an acceptor and a donor, into a three-dimensional network.

Related literature

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

Experimental

Crystal data

C₁₇H₁₆Cl₂N₂O₃·H₂O
M_r = 385.23
Monoclinic, C 2/c
a = 32.925 (3) Å
b = 7.3733 (7) Å
c = 15.1252 (13) Å
β = 92.319 (2)°
V = 3668.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 295 K
0.21 × 0.16 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.925, T_max = 0.960
9328 measured reflections
3242 independent reflections
2320 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.127
S = 1.01
3242 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.39 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	1.77	2.494 (2)	146
N2—H2⋯O4ⁱ	0.86	2.16	3.004 (2)	168
O4—H18⋯O2ⁱⁱ	0.85	1.97	2.815 (2)	171
O4—H19⋯O1ⁱⁱⁱ	0.85	2.11	2.908 (2)	155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536810037293/fl2314sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037293/fl2314Isup2.hkl

checkCIF report

Comment top

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

(I) displays a trans conformation with respect to the C7=N1 double bond (Fig. 1). The N2-N1=C7-C6 torsion angle is -175.44 (18)°.The dihedral angle between the two benzene rings is 30.77 (molecules are linked into a three dimensional network by intermolecular N-H···O, O-H···O Hydrogen bonds involving the water molecule which acts as both a donor and an acceptor.( Table. 1, Fig. 1and Fig. 2).

Related literature top

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

Experimental top

4-methoxybenzohydrazide (0.01 mol,1.66 g) was dissolved in anhydrous ethanol (40 ml), and 1-(3,5-dichloro-2-hydroxyphenyl)propan-1-one (0.01 mol, 2.19 g) was added. The reaction mixture was refluxed for 6 h with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 82%). The compound (1.0 mmol, 0.37 g) was dissolved in dimethylformamide (15 ml) and kept at room temperature for 30 d to obtain colourless 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 (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.Dashed lines show intramolecular O–H···N hydrogen bonds.
	Fig. 2. Packing diagram of (I), showing intermolecular O—H···O and N—H···O hydrogen bonds with the water molecule (dashed lines).

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

Crystal data top

C₁₇H₁₆Cl₂N₂O₃·H₂O	F(000) = 1600
M_r = 385.23	D_x = 1.395 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2261 reflections
a = 32.925 (3) Å	θ = 2.7–22.8°
b = 7.3733 (7) Å	µ = 0.38 mm⁻¹
c = 15.1252 (13) Å	T = 295 K
β = 92.319 (2)°	Block, colourless
V = 3668.9 (6) Å³	0.21 × 0.16 × 0.11 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	3242 independent reflections
Radiation source: fine-focus sealed tube	2320 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −38→31
T_min = 0.925, T_max = 0.960	k = −7→8
9328 measured reflections	l = −17→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0624P)² + 2.1699P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3242 reflections	Δρ_max = 0.29 e Å⁻³
230 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)

Crystal data top

C₁₇H₁₆Cl₂N₂O₃·H₂O	V = 3668.9 (6) Å³
M_r = 385.23	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 32.925 (3) Å	µ = 0.38 mm⁻¹
b = 7.3733 (7) Å	T = 295 K
c = 15.1252 (13) Å	0.21 × 0.16 × 0.11 mm
β = 92.319 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3242 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2320 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.960	R_int = 0.027
9328 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
3242 reflections	Δρ_min = −0.39 e Å⁻³
230 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	0.90858 (2)	0.20782 (14)	0.56665 (4)	0.0858 (3)
Cl2	0.96867 (2)	0.10906 (15)	0.90003 (5)	0.0939 (4)
N1	0.78571 (6)	0.0580 (3)	0.76338 (12)	0.0430 (5)
N2	0.74565 (5)	0.0416 (3)	0.78172 (11)	0.0449 (5)
H2	0.7378	0.0201	0.8342	0.054*
O1	0.83142 (5)	0.1268 (2)	0.64024 (10)	0.0538 (5)
H1	0.8097	0.1104	0.6635	0.081*
O2	0.73122 (5)	0.0679 (2)	0.63564 (10)	0.0550 (5)
O3	0.55192 (6)	0.1318 (3)	0.76671 (15)	0.0877 (7)
O4	0.28854 (6)	0.0811 (2)	0.04707 (10)	0.0605 (5)
H18	0.2830	0.0895	−0.0081	0.091*
H19	0.3050	0.1670	0.0597	0.091*
C1	0.86185 (7)	0.1190 (3)	0.70224 (14)	0.0445 (6)
C2	0.90114 (8)	0.1561 (4)	0.67682 (15)	0.0528 (6)
C3	0.93372 (8)	0.1525 (4)	0.73556 (18)	0.0636 (7)
H3	0.9597	0.1786	0.7172	0.076*
C4	0.92734 (8)	0.1095 (4)	0.82283 (17)	0.0596 (7)
C5	0.88941 (7)	0.0692 (3)	0.85008 (16)	0.0503 (6)
H5	0.8860	0.0387	0.9090	0.060*
C6	0.85555 (7)	0.0729 (3)	0.79125 (14)	0.0409 (5)
C7	0.81465 (7)	0.0354 (3)	0.82230 (14)	0.0397 (5)
C8	0.80792 (7)	−0.0152 (3)	0.91630 (14)	0.0437 (5)
H8A	0.8310	−0.0844	0.9394	0.052*
H8B	0.7840	−0.0916	0.9186	0.052*
C9	0.80230 (9)	0.1511 (4)	0.97375 (16)	0.0606 (7)
H9A	0.8275	0.2160	0.9799	0.091*
H9B	0.7939	0.1141	1.0311	0.091*
H9C	0.7819	0.2284	0.9466	0.091*
C10	0.71868 (7)	0.0615 (3)	0.71071 (14)	0.0418 (5)
C11	0.67535 (7)	0.0788 (3)	0.72990 (14)	0.0422 (5)
C12	0.66180 (7)	0.1335 (3)	0.81114 (15)	0.0505 (6)
H12	0.6807	0.1569	0.8570	0.061*
C13	0.62131 (8)	0.1540 (4)	0.82595 (17)	0.0584 (7)
H13	0.6130	0.1909	0.8812	0.070*
C14	0.59297 (8)	0.1198 (4)	0.75892 (19)	0.0593 (7)
C15	0.60576 (8)	0.0678 (4)	0.67635 (18)	0.0621 (7)
H15	0.5867	0.0458	0.6306	0.075*
C16	0.64623 (7)	0.0488 (3)	0.66187 (16)	0.0522 (6)
H16	0.6545	0.0154	0.6061	0.063*
C17	0.53716 (10)	0.1785 (6)	0.8521 (2)	0.1014 (12)
H17A	0.5465	0.0903	0.8950	0.152*
H17B	0.5080	0.1802	0.8491	0.152*
H17C	0.5472	0.2962	0.8692	0.152*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0798 (6)	0.1289 (8)	0.0498 (4)	−0.0187 (5)	0.0173 (4)	−0.0021 (4)
Cl2	0.0387 (4)	0.1699 (10)	0.0722 (5)	0.0028 (4)	−0.0099 (3)	0.0112 (5)
N1	0.0393 (11)	0.0532 (12)	0.0363 (10)	0.0011 (9)	−0.0018 (8)	0.0007 (9)
N2	0.0402 (11)	0.0603 (13)	0.0340 (10)	−0.0005 (9)	−0.0003 (8)	0.0058 (9)
O1	0.0489 (10)	0.0745 (12)	0.0378 (9)	−0.0036 (9)	−0.0019 (7)	0.0026 (8)
O2	0.0523 (10)	0.0788 (12)	0.0337 (9)	0.0002 (9)	−0.0012 (7)	0.0023 (8)
O3	0.0422 (11)	0.1199 (19)	0.1009 (17)	0.0046 (11)	0.0012 (11)	−0.0046 (14)
O4	0.0738 (12)	0.0694 (12)	0.0379 (9)	−0.0159 (9)	−0.0028 (8)	0.0036 (8)
C1	0.0480 (14)	0.0468 (13)	0.0385 (12)	0.0019 (11)	−0.0019 (10)	−0.0035 (10)
C2	0.0504 (15)	0.0648 (16)	0.0439 (13)	0.0003 (12)	0.0082 (11)	−0.0045 (12)
C3	0.0432 (15)	0.085 (2)	0.0629 (17)	0.0017 (13)	0.0084 (13)	−0.0052 (15)
C4	0.0411 (14)	0.082 (2)	0.0554 (15)	0.0071 (13)	−0.0029 (12)	−0.0018 (14)
C5	0.0442 (14)	0.0633 (16)	0.0432 (13)	0.0097 (11)	−0.0017 (11)	0.0019 (11)
C6	0.0415 (13)	0.0423 (13)	0.0388 (12)	0.0050 (10)	−0.0013 (9)	−0.0020 (10)
C7	0.0445 (13)	0.0384 (12)	0.0359 (11)	0.0038 (10)	−0.0023 (10)	−0.0016 (9)
C8	0.0425 (13)	0.0489 (13)	0.0395 (12)	0.0017 (10)	−0.0031 (10)	0.0053 (10)
C9	0.0770 (18)	0.0666 (17)	0.0383 (13)	−0.0001 (14)	0.0055 (12)	−0.0033 (12)
C10	0.0462 (13)	0.0414 (13)	0.0374 (13)	−0.0004 (10)	−0.0044 (10)	0.0002 (10)
C11	0.0426 (13)	0.0409 (12)	0.0425 (12)	−0.0026 (10)	−0.0062 (10)	0.0040 (10)
C12	0.0459 (14)	0.0614 (16)	0.0436 (13)	0.0016 (12)	−0.0049 (11)	−0.0010 (11)
C13	0.0532 (16)	0.0683 (18)	0.0541 (15)	0.0056 (13)	0.0049 (13)	0.0004 (13)
C14	0.0417 (14)	0.0641 (17)	0.0719 (18)	0.0013 (12)	0.0004 (13)	0.0059 (14)
C15	0.0477 (16)	0.0732 (19)	0.0638 (17)	−0.0041 (13)	−0.0179 (13)	−0.0016 (14)
C16	0.0525 (15)	0.0557 (15)	0.0476 (14)	−0.0007 (12)	−0.0073 (11)	−0.0025 (11)
C17	0.0529 (19)	0.139 (3)	0.114 (3)	0.009 (2)	0.0225 (19)	−0.006 (3)

Geometric parameters (Å, º) top

Cl1—C2	1.736 (2)	C7—C8	1.495 (3)
Cl2—C4	1.757 (3)	C8—C9	1.519 (3)
N1—C7	1.289 (3)	C8—H8A	0.9700
N1—N2	1.364 (3)	C8—H8B	0.9700
N2—C10	1.374 (3)	C9—H9A	0.9600
N2—H2	0.8600	C9—H9B	0.9600
O1—C1	1.346 (3)	C9—H9C	0.9600
O1—H1	0.8200	C10—C11	1.473 (3)
O2—C10	1.225 (3)	C11—C12	1.384 (3)
O3—C14	1.364 (3)	C11—C16	1.395 (3)
O3—C17	1.440 (4)	C12—C13	1.369 (3)
O4—H18	0.8499	C12—H12	0.9300
O4—H19	0.8500	C13—C14	1.373 (4)
C1—C2	1.392 (3)	C13—H13	0.9300
C1—C6	1.412 (3)	C14—C15	1.388 (4)
C2—C3	1.365 (3)	C15—C16	1.366 (4)
C3—C4	1.382 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.364 (3)	C17—H17A	0.9600
C5—C6	1.398 (3)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.470 (3)

C7—N1—N2	122.80 (18)	C8—C9—H9A	109.5
N1—N2—C10	115.55 (18)	C8—C9—H9B	109.5
N1—N2—H2	122.2	H9A—C9—H9B	109.5
C10—N2—H2	122.2	C8—C9—H9C	109.5
C1—O1—H1	109.5	H9A—C9—H9C	109.5
C14—O3—C17	117.7 (2)	H9B—C9—H9C	109.5
H18—O4—H19	106.0	O2—C10—N2	119.8 (2)
O1—C1—C2	118.2 (2)	O2—C10—C11	123.0 (2)
O1—C1—C6	122.7 (2)	N2—C10—C11	117.13 (19)
C2—C1—C6	119.0 (2)	C12—C11—C16	117.7 (2)
C3—C2—C1	122.1 (2)	C12—C11—C10	123.3 (2)
C3—C2—Cl1	119.4 (2)	C16—C11—C10	118.9 (2)
C1—C2—Cl1	118.50 (18)	C13—C12—C11	121.9 (2)
C2—C3—C4	118.7 (2)	C13—C12—H12	119.1
C2—C3—H3	120.6	C11—C12—H12	119.1
C4—C3—H3	120.6	C12—C13—C14	119.7 (2)
C5—C4—C3	121.0 (2)	C12—C13—H13	120.1
C5—C4—Cl2	119.5 (2)	C14—C13—H13	120.1
C3—C4—Cl2	119.5 (2)	O3—C14—C13	124.8 (3)
C4—C5—C6	121.3 (2)	O3—C14—C15	115.7 (2)
C4—C5—H5	119.3	C13—C14—C15	119.5 (2)
C6—C5—H5	119.3	C16—C15—C14	120.4 (2)
C5—C6—C1	117.9 (2)	C16—C15—H15	119.8
C5—C6—C7	120.7 (2)	C14—C15—H15	119.8
C1—C6—C7	121.45 (19)	C15—C16—C11	120.7 (2)
N1—C7—C6	114.57 (19)	C15—C16—H16	119.6
N1—C7—C8	123.8 (2)	C11—C16—H16	119.6
C6—C7—C8	121.57 (18)	O3—C17—H17A	109.5
C7—C8—C9	111.64 (19)	O3—C17—H17B	109.5
C7—C8—H8A	109.3	H17A—C17—H17B	109.5
C9—C8—H8A	109.3	O3—C17—H17C	109.5
C7—C8—H8B	109.3	H17A—C17—H17C	109.5
C9—C8—H8B	109.3	H17B—C17—H17C	109.5
H8A—C8—H8B	108.0

C7—N1—N2—C10	−177.1 (2)	C1—C6—C7—C8	179.4 (2)
O1—C1—C2—C3	179.5 (2)	N1—C7—C8—C9	−88.7 (3)
C6—C1—C2—C3	−1.2 (4)	C6—C7—C8—C9	88.0 (3)
O1—C1—C2—Cl1	−0.7 (3)	N1—N2—C10—O2	9.7 (3)
C6—C1—C2—Cl1	178.64 (18)	N1—N2—C10—C11	−168.88 (19)
C1—C2—C3—C4	0.4 (4)	O2—C10—C11—C12	−157.1 (2)
Cl1—C2—C3—C4	−179.4 (2)	N2—C10—C11—C12	21.4 (3)
C2—C3—C4—C5	0.7 (4)	O2—C10—C11—C16	19.2 (3)
C2—C3—C4—Cl2	−178.6 (2)	N2—C10—C11—C16	−162.3 (2)
C3—C4—C5—C6	−1.1 (4)	C16—C11—C12—C13	1.4 (4)
Cl2—C4—C5—C6	178.2 (2)	C10—C11—C12—C13	177.8 (2)
C4—C5—C6—C1	0.3 (4)	C11—C12—C13—C14	0.0 (4)
C4—C5—C6—C7	−177.8 (2)	C17—O3—C14—C13	−1.9 (4)
O1—C1—C6—C5	−179.9 (2)	C17—O3—C14—C15	177.7 (3)
C2—C1—C6—C5	0.8 (3)	C12—C13—C14—O3	178.4 (2)
O1—C1—C6—C7	−1.8 (3)	C12—C13—C14—C15	−1.1 (4)
C2—C1—C6—C7	178.9 (2)	O3—C14—C15—C16	−178.9 (3)
N2—N1—C7—C6	−175.44 (18)	C13—C14—C15—C16	0.7 (4)
N2—N1—C7—C8	1.4 (3)	C14—C15—C16—C11	0.8 (4)
C5—C6—C7—N1	174.4 (2)	C12—C11—C16—C15	−1.9 (4)
C1—C6—C7—N1	−3.6 (3)	C10—C11—C16—C15	−178.4 (2)
C5—C6—C7—C8	−2.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.77	2.494 (2)	146
N2—H2···O4ⁱ	0.86	2.16	3.004 (2)	168
O4—H18···O2ⁱⁱ	0.85	1.97	2.815 (2)	171
O4—H19···O1ⁱⁱⁱ	0.85	2.11	2.908 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆Cl₂N₂O₃·H₂O
M_r	385.23
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	32.925 (3), 7.3733 (7), 15.1252 (13)
β (°)	92.319 (2)
V (Å³)	3668.9 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.21 × 0.16 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.925, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	9328, 3242, 2320
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.127, 1.01
No. of reflections	3242
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.39

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
O1—H1···N1	0.82	1.77	2.494 (2)	145.5
N2—H2···O4ⁱ	0.86	2.16	3.004 (2)	167.9
O4—H18···O2ⁱⁱ	0.85	1.97	2.815 (2)	171.1
O4—H19···O1ⁱⁱⁱ	0.85	2.11	2.908 (2)	155.4

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

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (grant 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. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2620

doi:10.1107/S1600536810037293

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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